TW202019889A - 3-(1h-1,2,4-triazol-1-yl) benzoic acid amide derivative and pest control agent - Google Patents

3-(1h-1,2,4-triazol-1-yl) benzoic acid amide derivative and pest control agent Download PDF

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TW202019889A
TW202019889A TW108129126A TW108129126A TW202019889A TW 202019889 A TW202019889 A TW 202019889A TW 108129126 A TW108129126 A TW 108129126A TW 108129126 A TW108129126 A TW 108129126A TW 202019889 A TW202019889 A TW 202019889A
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alkyl
haloalkyl
cycloalkyl
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榎本幸浩
志鎌大介
田中皓祐
鳥谷部啓二
村松義浩
阿部晋
高根澤陽
松田武
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日商組合化學工業股份有限公司
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/647—Triazoles; Hydrogenated triazoles
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    • A—HUMAN NECESSITIES
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    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
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    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
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    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
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    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
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    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
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    • C07—ORGANIC CHEMISTRY
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    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Abstract

An object of the present invention is to provide an excellent pest control agent. The present invention provides a pest control agent which contains 3-(1H-1,2,4-triazol-1-yl) benzoic acid amide derivative represented by the general formula [I] or an agriculturally acceptable salt thereof as an active ingredient. [In the formula, R1 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6 cycloalkyl group or the likes, R2 represents a hydrogen atom, A represents an oxygen atom or a sulfur atom, R3 represents a halogen atom, a C1-C6 alkyl group or the likes, n represents an integer of 0-3, R4 represents a halogen atom, a C1-C6 alkyl group or the likes, R5 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, -NH2, -N(R12)R14 or the likes, R6 represents a hydrogen atom, a C1-C6 alkyl group, -NH2, -N(R12)R14, -N(R10)C(=O)R14 or the likes].

Description

3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物及有害生物防除劑 3-(1H-1,2,4-triazol-1-yl)benzamide derivatives and pest control agents

本發明係關於新穎的3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物或其農業上可容許之鹽、含有該衍生物或其鹽作為有效成分之有害生物防除劑及製造中間物。 The present invention relates to a novel 3-(1H-1,2,4-triazol-1-yl)benzamide derivative or its agriculturally acceptable salt, containing the derivative or its salt as an active ingredient Pest control agent and manufacturing intermediates.

於專利文獻1與2中係記載一種具有有害生物防除效果之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物。專利文獻1與2所記載之化合物僅限定於在鍵結於苯甲醯胺的3號位之***環的3號位上鍵結有1H-吡唑-5-基之化合物。 Patent Documents 1 and 2 describe a 3-(1H-1,2,4-triazol-1-yl)benzamide derivative having a pest control effect. The compounds described in Patent Documents 1 and 2 are limited to compounds in which 1H-pyrazol-5-yl is bonded to the 3rd position of the triazole ring at the 3rd position of benzamide.

於專利文獻3中係記載一種具有P2X3或P2X2/3受體拮抗劑活性之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物。專利文獻3所記載之化合物僅限定於在苯甲醯胺的5號位上鍵結有5-甲基吡啶-2-基之化合物。再者，於專利文獻3中亦無任何關於殺蟲活性之記載。 Patent Document 3 describes a 3-(1H-1,2,4-triazol-1-yl)benzamide derivative having P2X3 or P2X2/3 receptor antagonist activity. The compound described in Patent Document 3 is limited to compounds in which 5-methylpyridin-2-yl is bonded to the 5-position of benzamide. In addition, Patent Document 3 does not have any description about insecticidal activity.

於專利文獻4中係記載一種具有P2X7受體阻礙活性之苯甲醯胺衍生物。專利文獻4所記載之化合物雖是在苯甲醯胺的3號位上鍵結有4,5-二氫-5-側氧基-1H-1,2,4-***-1-基之化合物，但僅限定於N-(經羥基取代之環烷基烷基)苯甲醯胺。於專利文獻4中亦無任何關於殺蟲活性之記載。 Patent Document 4 describes a benzamide derivative having P2X7 receptor inhibitory activity. Although the compound described in Patent Document 4 has 4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl bonded to the 3-position of benzamide Compounds, but only limited to N-(hydroxyalkyl substituted cycloalkylalkyl) benzamide. In Patent Document 4, there is no record about insecticidal activity.

於專利文獻5中係記載一種具有除草活性之苯基胺磺醯基接醯胺衍生物。專利文獻5所記載之化合物僅限定於在苯基胺磺醯基羧醯胺的3號位上鍵結有4,5-二氫-5-側氧基-1H-1,2,4-***-1-基之化合物。再者，於專利文獻5中亦無任何關於殺蟲活性之記載。 Patent Document 5 describes a herbicidal activity of phenylamine sulfonamide amide derivatives. The compound described in Patent Document 5 is only limited to 4,5-dihydro-5-pentoxy-1H-1,2,4-triphenylene bonded to the 3-position of phenylsulfamoylcarboxamide Azole-1-yl compounds. In addition, Patent Document 5 does not have any description about insecticidal activity.

於專利文獻6中係記載一種具有Xa因子阻礙活性之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物。專利文獻6所記載之化合物僅限定於在***環的5號位上鍵結有苯基胺基羰基、吡啶基胺基羰基、嘧啶基胺基羰基之化合物。再者，於專利文獻6中亦無任何關於殺蟲活性之記載。 Patent Document 6 describes a 3-(1H-1,2,4-triazol-1-yl)benzamide derivative having factor Xa inhibitory activity. The compound described in Patent Document 6 is limited to compounds in which a phenylaminocarbonyl group, a pyridylaminocarbonyl group, and a pyrimidinylaminocarbonyl group are bonded to the 5-position of the triazole ring. In addition, Patent Document 6 does not have any description about insecticidal activity.

[先前技術文獻] [Prior Technical Literature] [專利文獻] [Patent Literature]

[專利文獻1]國際公開第2017/108569號 [Patent Literature 1] International Publication No. 2017/108569

[專利文獻2]國際公開第2017/012970號 [Patent Literature 2] International Publication No. 2017/012970

[專利文獻3]國際公開第2009/077366號 [Patent Document 3] International Publication No. 2009/077366

[專利文獻4]國際公開第2004/058731號 [Patent Document 4] International Publication No. 2004/058731

[專利文獻5]國際公開第2001/083459號 [Patent Literature 5] International Publication No. 2001/083459

[專利文獻6]國際公開第1998/028269號 [Patent Literature 6] International Publication No. 1998/028269

對有用作物使用之有害生物防除劑，較佳為施用在土壤或莖葉且在低藥量下即顯示充分的有害生物防除效果之藥劑。再者，對於化學物質的安全性以及對環境帶來之影響之要求逐漸增高，期待著開發出更安全的有害生物防除劑。再者，近年來由於長期使用殺蟲劑、殺蟎劑、殺線蟲劑等有害生物防除劑，逐漸出現對該有害生物防除劑具有抵抗性之有害生物，因而完全地防除有害生物變得困難。再者，關於人畜毒性高之有害生物防除劑的使用，對於作業人員而言有安全性等方面之問題。 The pest control agent used for useful crops is preferably an agent applied to soil or stems and leaves and showing sufficient pest control effect at a low dose. In addition, the requirements for the safety of chemical substances and the impact on the environment are gradually increasing, and we look forward to developing safer pest control agents. Furthermore, in recent years, due to the long-term use of pest control agents such as insecticides, acaricides, and nematicides, pests that are resistant to the pest control agents have gradually appeared, so it has become difficult to completely control the pests. Furthermore, the use of pest control agents with high toxicity to humans and animals poses safety and other problems for the workers.

本發明之課題係於如此的情況下，提供一種解決以往有害生物防除劑所具有之前述般的問題，進一步具有優異的安全性、防除效果、殘效性等之有害生物防除劑、以及一種用於此之新穎的化合物。 The object of the present invention is to provide a pest control agent that solves the aforementioned problems of conventional pest control agents, further has excellent safety, control effect, residual effect, etc. This is a novel compound.

本發明者們為了開發出具有前述較佳特性之有害生物防除劑，係合成各種3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物並對其生理活性進行精心探討。結果發現以下述通式[I]所表示之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物(以下，亦稱為本發明之化合物)對於各種有害生物具有優異的防除效果，更持續地進行研究進而完成本發明。 The present inventors synthesized various 3-(1H-1,2,4-triazol-1-yl)benzamide derivatives and developed their physiological activities in order to develop a pest control agent with the aforementioned preferred characteristics Have a careful discussion. As a result, it was found that 3-(1H-1,2,4-triazol-1-yl)benzamide derivatives (hereinafter, also referred to as the compounds of the present invention) represented by the following general formula [I] are harmful to various The organism has an excellent control effect, and more continuous research is carried out to complete the present invention.

亦即，本發明係關於下述事項者。 That is, the present invention relates to the following matters.

(1)一種下述通式[I]表示之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物或其農業上所容許之鹽， (1) A 3-(1H-1,2,4-triazol-1-yl) benzamide derivative represented by the following general formula [I] or its agriculturally acceptable salt,

Figure 108129126-A0202-12-0004-207
Figure 108129126-A0202-12-0004-207

式中， In the formula,

R1表示氫原子、C1至C6烷基、C1至C6鹵烷基、經R7任意地取代之C1至C6烷基、C3至C6環烷基、C3至C6鹵環烷基、經R8任意地取代之C3至C6環烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、-NH2、-N(R9)R10、-OH、-OR11、-S(=O)2R11、-CH=NOR11或飽和雜環， R 1 represents a hydrogen atom, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl, optionally substituted by R 7 of a C 1 to C 6 alkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, C 3 to C 6 cycloalkyl optionally substituted by R 8 , C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 To C 6 haloalkynyl, -NH 2 , -N(R 9 )R 10 , -OH, -OR 11 , -S(=O) 2 R 11 , -CH=NOR 11, or saturated heterocyclic ring,

R2表示氫原子、氰基、C1至C6烷基、C1至C6鹵烷基、經R7任意地取代之C1至C6烷基、C3至C6環烷基、C2至C6烯基、C2至C6炔基、-S(=O)2R11、-C(=O)R11、-C(=O)OR11、-C(=O)NH2、-C(=O)N(R12)R11、-C(=O)N(R12)OR11，或是R1及R2可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 2 represents a hydrogen atom, a cyano group, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a C 1 to C 6 alkyl group optionally substituted by R 7 , a C 3 to C 6 cycloalkyl group, C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, -S(=O) 2 R 11 , -C(=O)R 11 , -C(=O)OR 11 , -C(=O) NH 2 , -C(=O)N(R 12 )R 11 , -C(=O)N(R 12 )OR 11 , or R 1 and R 2 can be bonded to each other to form C 2 to C 6 Alkylene bond, in which case the alkylene bond can contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond can be monovalent by halogen atom or C 1 to C 6 alkyl group Replace or replace more,

A表示氧原子或硫原子， A represents an oxygen atom or a sulfur atom,

R3表示鹵素原子、氰基、C1至C6烷基、C1至C6鹵烷基、C1至C6烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、-NH2、-N(R9)R10、-C(=O)NH2或-C(=S)NH2， R 3 represents a halogen atom, cyano group, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, C 1 to C 6 alkoxy group, C 1 to C 6 alkylthio group, C 1 to C 6 Alkylsulfinyl, C 1 to C 6 alkylsulfonyl, -NH 2 , -N(R 9 )R 10 , -C(=O)NH 2 or -C(=S)NH 2 ,

n表示0至3的整數， n represents an integer from 0 to 3,

R4表示鹵素原子、氰基、硝基、C1至C6烷基、C1至C6烷氧基C1至C6烷基、C1至C6烷基硫基C1至C6烷基、氰基C1至C6烷基、C1至C6鹵烷基、C3至C6環烷基、C3至C6鹵環烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、-OH、C1至C6烷氧基、C1至C6鹵烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、-NH2或-N(R9)R10， R 4 represents a halogen atom, cyano, nitro, C 1 to C 6 alkyl, C 1 to C 6 alkoxy C 1 to C 6 alkyl, C 1 to C 6 alkylthio C 1 to C 6 Alkyl, cyano C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, -OH, C 1 to C 6 alkoxy, C 1 to C 6 haloalkoxy, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfinyl, C 1 to C 6 haloalkylthio, C 1 to C 6 haloalkyl Sulfonyl, C 1 to C 6 haloalkyl sulfonyl, -NH 2 or -N(R 9 )R 10 ,

R5表示氫原子、鹵素原子、氰基、硝基、C1至C6烷基、C1至C6鹵烷基、經R13任意地取代之C1至C6烷基、經R13任意地取代之C1至C6鹵烷基、C3至C6環烷基、C3至C6鹵環烷基、經R8任意地取代之C3至C6環烷基、C2至C6烯基、C2至C6鹵烯基、經R13任意地取代之C2至C6烯基、C2至C6炔基、C2至C6鹵炔基、經R13任意地取代之C2至C6炔基、-OH、-OC(=O)R14、-OS(=O)2R14、-OSi(R14)2R12、C1至C6烷氧基、C1至C6鹵烷氧基、經R13任意地取代之C1至C6烷氧基、經R13任意地取代之C1至C6鹵烷氧基、C2至C6烯基氧基、C2至C6鹵烯基氧基、C2至C6炔基氧基、C2至C6鹵炔基氧基、C3至C6環烷基氧基、C3至C6鹵環烷基氧基、無取代或經(Z)p1取代之苯基氧基、芳香族雜環氧基、飽和雜環氧基、-SH、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、經R13任意地取代之C1至C6烷基硫基、經R13任意地取代之C1至C6烷基亞磺醯基、經R13任意地取代之C1至C6烷基磺醯基、經R13任意地取代之C1至C6鹵烷基硫基、經R13任意地取代之C1至C6鹵烷基亞磺醯基、經R13任意地取 代之C1至C6鹵烷基磺醯基、C2至C6烯基硫基、C2至C6烯基亞磺醯基、C2至C6烯基磺醯基、C2至C6鹵烯基硫基、C2至C6鹵烯基亞磺醯基、C2至C6鹵烯基磺醯基、C2至C6炔基硫基、C2至C6炔基亞磺醯基、C2至C6炔基磺醯基、C3至C6環烷基硫基、C3至C6環烷基亞磺醯基、C3至C6環烷基磺醯基、無取代或經(Z)p1取代之苯基硫基、無取代或經(Z)p1取代之苯基亞磺醯基、無取代或經(Z)p1取代之苯基磺醯基、芳香族雜環硫基、芳香族雜環亞磺醯基、芳香族雜環磺醯基、飽和雜環硫基、飽和雜環亞磺醯基、飽和雜環磺醯基、-NH2、-N(R12)R14、-N(R10)C(=O)H、-N(R10)C(=O)R14、-N(R10)C(=O)OR14、-N(R10)C(=O)NH2、-N(R10)C(=O)N(R12)R14、-N(R10)C(=O)N(R12)OR14、-N(R10)C(=S)NH2、-N(R10)C(=S)N(R12)R14、-N(R10)S(=O)2R14、-N(R10)S(=O)2NH2、-N(R10)S(=O)2N(R12)R14、-C(=O)H、-C(=O)R14、-C(=O)OH、-C(=O)OR14、-C(=O)NH2、-C(=O)N(R12)R14、-C(=O)N(R12)OR14、-C(R15)=NOH或-C(R15)=NOR14， R 5 represents a hydrogen atom, a halogen atom, cyano, nitro, C 1 to C 6 -alkyl, C 1 to C 6 haloalkyl, optionally substituted with R of C 13 1 to C 6 alkyl, R 13 the optionally substituted with a C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, optionally substituted with R of C 8 3 to C 6 cycloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl group, with R optionally substituted with of C 13 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, by R 13 Optionally substituted C 2 to C 6 alkynyl, -OH, -OC(=O)R 14 , -OS(=O) 2 R 14 , -OSi(R 14 ) 2 R 12 , C 1 to C 6 alkane group, C 1 to C 6 haloalkoxy, optionally substituted by R 13 of a C 1 to C 6 alkoxy, optionally substituted by R 13 of a C 1 to C 6 haloalkoxy, C 2 to C 6 alkenyloxy, C 2 to C 6 haloalkenyloxy, C 2 to C 6 alkynyloxy, C 2 to C 6 haloalkynyloxy, C 3 to C 6 cycloalkyloxy, C 3 to C 6 halocycloalkyloxy, unsubstituted or substituted (Z)p 1 phenyloxy, aromatic heterocyclic oxy, saturated heterocyclic oxy, -SH, C 1 to C 6 alkyl Thio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 haloalkylthio, C 1 to C 6 haloalkylsulfinyl, a C 1 to C 6 haloalkyl sulfo acyl, optionally substituted by R 13 of a C 1 to C 6 alkylthio, optionally substituted by R of C 13 1 to C 6 alkylsulfinyl acyl, with R 13 of optionally substituted a C 1 to C 6 alkylsulfonyl group, optionally substituted by R of C 13 1 to C 6 haloalkyl group, optionally substituted by R of C 13 1 to C 6 alkylsulfinyl halo Sulfonyl, C 1 to C 6 haloalkyl sulfonyl optionally substituted by R 13 , C 2 to C 6 alkenylthio, C 2 to C 6 alkenylsulfinyl, C 2 to C 6 Alkenylsulfonyl, C 2 to C 6 haloalkenylthio, C 2 to C 6 haloalkenylsulfinyl, C 2 to C 6 haloalkenylsulfonyl, C 2 to C 6 alkynylsulfide group, C 2 to C 6 alkynyl alkylsulfinyl acyl, C 2 to C 6 alkynyl group sulfo acyl, C 3 to C 6 cycloalkyl group, C 3 to C 6 cycloalkyl acyl alkylsulfinyl, C 3 to C 6 cycloalkylsulfonyl, unsubstituted or substituted with (Z)p 1 phenylthio, unsubstituted or substituted with (Z)p 1 phenylsulfinyl, unsubstituted or substituted ( Z) P 1 substituted phenylsulfonyl, aromatic heterocyclic sulfenyl, aromatic heterocyclic sulfenyl, aromatic heterocyclic sulfonyl, saturated heterocyclic sulfenyl, saturated heterocyclic sulfenyl, Saturated heterocyclic sulfonyl, -NH 2 , -N(R 12 )R 14 , -N(R 10 )C(=O)H, -N(R 10 )C(=O )R 14 , -N(R 10 )C(=O)OR 14 , -N(R 10 )C(=O)NH 2 , -N(R 10 )C(=O)N(R 12 )R 14 , -N(R 10 )C(=O)N(R 12 )OR 14 , -N(R 10 )C(=S)NH 2 , -N(R 10 )C(=S)N(R 12 ) R 14 , -N(R 10 )S(=O) 2 R 14 , -N(R 10 )S(=O) 2 NH 2 , -N(R 10 )S(=O) 2 N(R 12 ) R 14 , -C(=O)H, -C(=O)R 14 , -C(=O)OH, -C(=O)OR 14 , -C(=O)NH 2 , -C(= O)N(R 12 )R 14 , -C(=O)N(R 12 )OR 14 , -C(R 15 )=NOH or -C(R 15 )=NOR 14 ,

R6表示氫原子、鹵素原子、氰基、硝基、C1至C6烷基、C1至C6鹵烷基、經R7任意地取代之C1至C6烷基、C3至C6環烷基、C3至C6鹵環烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、-OH、C1至C6烷氧基、C1至C6鹵烷氧基、經R7任意地取代之C1至C6烷氧基、C2至C6烯基氧基、C2至C6鹵烯基氧基、C2至C6炔基氧基、C2至C6鹵炔基氧基、C3至C6環烷基氧基、C3至C6鹵環烷基氧基、-SH、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、C2至C6烯基硫基、C2至C6烯基亞磺醯基、C2至C6烯基磺醯基、C2至C6炔基硫 基、C2至C6炔基亞磺醯基、C2至C6炔基磺醯基、C3至C6環烷基硫基、C3至C6環烷基亞磺醯基、C3至C6環烷基磺醯基、-NH2、-N(R12)R14、-N(R10)C(=O)H、-N(R10)C(=O)R14、-N(R10)C(=O)OR14、-N(R10)C(=O)NH2、-N(R10)C(=O)N(R12)R14、-N(R10)C(=O)N(R12)OR14、-N(R10)C(=S)NH2、-N(R10)C(=S)N(R12)R14、-N(R10)S(=O)2R14、-N(R10)S(=O)2NH2、-N(R10)S(=O)2N(R12)R14、-N=C(R12)R14、-N=C(R15)N(R12)R14、-NHC(R15)=NOR14、-N=S(R14)R12、-N=S(=O)(R14)R12、-N(R10)NH2、-N(R10)N(R12)R14、-N(R10)N(R10)C(=O)H、-N(R10)N(R10)C(=O)R14、-N(R10)N(R10)C(=O)OR14、-N(R10)N(R10)S(=O)2R14、-C(=O)H、-C(=O)R14、-C(R15)=NOH、-C(R15)=NOR14、-C(=O)OH、-C(=O)OR14、-C(=O)NH2或-C(=O)N(R12)R11， R 6 represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a C 1 to C 6 alkyl group optionally substituted by R 7 , a C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, -OH, a C 1 to C 6 alkoxy group, C 1 to C 6 haloalkoxy, optionally substituted by R 7 of a C 1 to C 6 alkoxy, C 2 to C 6 alkenyloxy, C 2 To C 6 haloalkenyloxy, C 2 to C 6 alkynyloxy, C 2 to C 6 haloalkynyloxy, C 3 to C 6 cycloalkyloxy, C 3 to C 6 halocycloalkyl Oxygen, -SH, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 haloalkylthio, C 1 to C 6 haloalkylsulfinyl, C 1 to C 6 haloalkylsulfonyl, C 2 to C 6 alkenylthio, C 2 to C 6 alkenylsulfinyl, C 2 to C 6 alkenylsulfonyl, C 2 to C 6 alkynylsulfanyl, C 2 to C 6 alkynylsulfinyl, C 2 to C 6 alkynylsulfonyl, C 3 to C 6 cycloalkylsulfide Group, C 3 to C 6 cycloalkylsulfinyl, C 3 to C 6 cycloalkylsulfonyl, -NH 2 , -N(R 12 )R 14 , -N(R 10 )C(=O )H, -N(R 10 )C(=O)R 14 , -N(R 10 )C(=O)OR 14 , -N(R 10 )C(=O)NH 2 , -N(R 10 )C(=O)N(R 12 )R 14 , -N(R 10 )C(=O)N(R 12 )OR 14 , -N(R 10 )C(=S)NH 2 , -N( R 10 )C(=S)N(R 12 )R 14 , -N(R 10 )S(=O) 2 R 14 , -N(R 10 )S(=O) 2 NH 2 , -N(R 10 )S(=O) 2 N(R 12 )R 14 , -N=C(R 12 )R 14 , -N=C(R 15 )N(R 12 )R 14 , -NHC(R 15 )= NOR 14 , -N=S(R 14 )R 12 , -N=S(=O)(R 14 )R 12 , -N(R 10 )NH 2 , -N(R 10 )N(R 12 )R 14 , -N(R 10 )N(R 10 )C(=O)H, -N(R 10 )N(R 10 )C(=O)R 14 , -N(R 10 )N(R 10 ) C(=O)OR 14 , -N(R 10 )N(R 10 )S(=O) 2 R 14 , -C(=O)H, -C(=O )R 14 , -C(R 15 )=NOH, -C(R 15 )=NOR 14 , -C(=O)OH, -C(=O)OR 14 , -C(=O)NH 2 or- C(=O)N(R 12 )R 11 ,

R7表示氰基、C3至C6環烷基、C3至C6鹵環烷基、-OH、C1至C6烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、-C(=O)OH、-C(=O)OR11、-C(=O)NH2或-C(=O)N(R12)R11， R 7 represents cyano, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, -OH, C 1 to C 6 alkoxy, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, -C(=O)OH, -C(=O)OR 11 , -C(=O)NH 2 or -C(= O)N(R 12 )R 11 ,

R8表示氰基、C1至C6烷基、C1至C6鹵烷基、C3至C6環烷基、C3至C6鹵環烷基、-C(=O)OR11、-C(=O)NH2或-C(=O)N(R12)R11， R 8 represents cyano, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, -C(=O)OR 11 , -C(=O)NH 2 or -C(=O)N(R 12 )R 11 ,

R9表示C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6炔基、C3至C6環烷基、-C(=O)H、-C(=O)R11、-C(=O)OR11、-C(=O)NH2、-C(=O)N(R12)R11或-S(=O)2R11， R 9 represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 3 to C 6 cycloalkyl, -C(=O )H, -C(=O)R 11 , -C(=O)OR 11 , -C(=O)NH 2 , -C(=O)N(R 12 )R 11 or -S(=O) 2 R 11 ,

R10表示氫原子、C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6炔基、C3至C6環烷基、-C(=O)R11、-C(=O)OR11或-S(=O)2R11，或是R9及R10可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1 個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 10 represents a hydrogen atom, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 3 to C 6 cycloalkyl, -C (=O)R 11 , -C(=O)OR 11 or -S(=O) 2 R 11 , or R 9 and R 10 may be bonded to each other to form a C 2 to C 6 alkylene bond, At this time, the alkylene bond may contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond may be mono- or multi-substituted by a halogen atom or a C 1 to C 6 alkyl group,

R11表示C1至C6烷基、C1至C6鹵烷基、C1至C6烷氧基C1至C6烷基、C1至C6烷基硫C1至C6烷基、氰基C1至C6烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基或C3至C6鹵環烷基， R 11 represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy C 1 to C 6 alkyl, C 1 to C 6 alkyl sulfur C 1 to C 6 alkyl Group, cyano C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl or C 3 to C 6 halocycloalkyl,

R12表示氫原子、氰基、C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基或C3至C6鹵環烷基，或是R11及R12可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 12 represents a hydrogen atom, cyano group, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, C 2 to C 6 alkenyl group, C 2 to C 6 haloalkenyl group, C 2 to C 6 alkynyl group , C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl or C 3 to C 6 halocycloalkyl, or R 11 and R 12 may be bonded to each other to form C 2 to C 6 alkylene Base bond, this alkylene bond may contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond may be mono-substituted by halogen atom or C 1 to C 6 alkyl group or Replace more,

R13表示氰基、C3至C6環烷基、C3至C6鹵環烷基、-OH、-OR14、-OC(=O)R14、-OS(=O)2R14、-OSi(R14)2R12、-SH、-SR14、-S(=O)R14、-S(=O)2R14、-S(=O)2N(R12)R14、-NH2、-N(R12)R14、-N(R10)C(=O)H、-N(R10)C(=O)R14、-N(R10)C(=O)OR14、-N(R10)C(=O)NH2、-N(R10)C(=O)N(R12)R14、-N(R10)C(=O)N(R12)OR14、-N(R10)C(=S)NH2、-N(R10)C(=S)N(R12)R14、-N(R10)S(=O)2R14、-N(R10)S(=O)2NH2、-N(R10)S(=O)2N(R12)R14、-C(=O)H、-C(=O)R14、-C(=O)OH、-C(=O)OR14、-C(=O)NH2、-C(=O)N(R12)R14、-C(=S)NH2、-C(=S)N(R12)R14、-C(R15)=NOH、-C(R15)=NOR14、-Si(R14)2R12、無取代或經(Z)p1取代之苯基、芳香族雜環或飽和雜環， R 13 represents cyano, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, -OH, -OR 14 , -OC(=O)R 14 , -OS(=O) 2 R 14 , -OSi(R 14 ) 2 R 12 , -SH, -SR 14 , -S(=O)R 14 , -S(=O) 2 R 14 , -S(=O) 2 N(R 12 )R 14 , -NH 2 , -N(R 12 )R 14 , -N(R 10 )C(=O)H, -N(R 10 )C(=O)R 14 , -N(R 10 )C( =O)OR 14 , -N(R 10 )C(=O)NH 2 , -N(R 10 )C(=O)N(R 12 )R 14 , -N(R 10 )C(=O) N(R 12 )OR 14 , -N(R 10 )C(=S)NH 2 , -N(R 10 )C(=S)N(R 12 )R 14 , -N(R 10 )S(= O) 2 R 14 , -N(R 10 )S(=O) 2 NH 2 , -N(R 10 )S(=O) 2 N(R 12 )R 14 , -C(=O)H,- C(=O)R 14 , -C(=O)OH, -C(=O)OR 14 , -C(=O)NH 2 , -C(=O)N(R 12 )R 14 , -C (=S)NH 2 , -C(=S)N(R 12 )R 14 , -C(R 15 )=NOH, -C(R 15 )=NOR 14 , -Si(R 14 ) 2 R 12 , Unsubstituted or substituted (Z)p 1 phenyl, aromatic heterocyclic or saturated heterocyclic,

R14表示C1至C6烷基、C1至C6鹵烷基、C1至C6烷氧基C1至C6烷基、C1至C6烷基硫C1至C6烷基、氰基C1至C6烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基、C3至C6鹵環烷基、無取代或經(Z)p1取代之苯基、無取代或經(Z)p1取代之苯基C1至C6烷基、芳香族雜環、芳香族雜環C1至C6烷基、飽和雜環或飽和雜環C1至C6烷基，或是R12及R14可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 14 represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy C 1 to C 6 alkyl, C 1 to C 6 alkyl sulfur C 1 to C 6 alkyl Group, cyano C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, unsubstituted or substituted with (Z)p 1 phenyl, unsubstituted or substituted with (Z)p 1 phenyl C 1 to C 6 alkyl, Aromatic heterocycle, aromatic heterocycle C 1 to C 6 alkyl, saturated heterocycle or saturated heterocycle C 1 to C 6 alkyl, or R 12 and R 14 may be bonded to each other to form C 2 to C 6 alkylene bond, in which case the alkylene bond can contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond can be performed by a halogen atom or a C 1 to C 6 alkyl group Single or multiple substitution,

R15表示氫原子、鹵素原子、-NH2、氰基、C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基或C3至C6鹵環烷基，或是R14及R15可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 15 represents a hydrogen atom, a halogen atom, -NH 2 , cyano, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl or C 3 to C 6 halocycloalkyl, or R 14 and R 15 may be bonded to each other to form C 2 to C 6 alkylene bond, in which case the alkylene bond can contain 1 oxygen atom, sulfur atom or nitrogen atom, and C 2 to C 6 alkylene bond can be through halogen atom or C 1 to C 6 alkyl groups are mono- or poly-substituted,

Z表示鹵素原子、氰基、硝基、C1至C6烷基、C1至C6鹵烷基、-OH、C1至C6烷氧基、C1至C6鹵烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、-NH2、單(C1至C6烷基)胺基、二(C1至C6烷基)胺基、C1至C6烷基羰基胺基、N-(C1至C6烷基羰基)-N-(C1至C6烷基)胺基、C1至C6烷氧基羰基胺基、N-(C1至C6烷氧基羰基)-N-(C1至C6烷基)胺基、C1至C6烷基磺醯基胺基、N-(C1至C6烷基磺醯基)-N-(C1至C6烷基)胺基、C1至C6鹵烷基磺醯基胺基、N-(C1至C6鹵烷基磺醯基)-N-(C1 至C6烷基)胺基、-C(=O)NH2、單(C1至C6烷基)胺基羰基、二(C1至C6烷基)胺基羰基、單(C1至C6鹵烷基)胺基羰基或苯基， Z represents halogen atom, cyano group, nitro group, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, -OH, C 1 to C 6 alkoxy group, C 1 to C 6 haloalkoxy group, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 haloalkylthio, C 1 to C 6 halo Alkylsulfinyl, C 1 to C 6 haloalkylsulfonyl, -NH 2 , mono(C 1 to C 6 alkyl)amino, di(C 1 to C 6 alkyl)amino, C 1 to C 6 alkylcarbonylamino, N-(C 1 to C 6 alkylcarbonyl)-N-(C 1 to C 6 alkyl)amino, C 1 to C 6 alkoxycarbonylamino, N -(C 1 to C 6 alkoxycarbonyl)-N-(C 1 to C 6 alkyl)amino, C 1 to C 6 alkylsulfonylamino, N-(C 1 to C 6 alkyl) Sulfonyl)-N-(C 1 to C 6 alkyl)amino, C 1 to C 6 haloalkylsulfonylamino, N-(C 1 to C 6 haloalkylsulfonyl)-N -(C 1 to C 6 alkyl)amino, -C(=O)NH 2 , mono(C 1 to C 6 alkyl)aminocarbonyl, di(C 1 to C 6 alkyl)aminocarbonyl, Mono(C 1 to C 6 haloalkyl)aminocarbonyl or phenyl,

芳香族雜環表示下列者， Aromatic heterocycle means the following,

Figure 108129126-A0202-12-0010-208
Figure 108129126-A0202-12-0010-208

飽和雜環表示下列者， Saturated heterocycle means the following,

Figure 108129126-A0202-12-0010-209
Figure 108129126-A0202-12-0010-209

p1表示0至5的整數， p 1 represents an integer from 0 to 5,

p2表示0至4的整數， p 2 represents an integer from 0 to 4,

p3表示0至3的整數， p 3 represents an integer from 0 to 3,

p4表示0至2的整數， p 4 represents an integer from 0 to 2,

t表示0或1的整數。 t represents an integer of 0 or 1.

(2)一種農藥組成物，該農藥組成物係含有前述(1)所述之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物或其農業上所容許之鹽作為有效成分。 (2) A pesticide composition containing the 3-(1H-1,2,4-triazol-1-yl)benzamide derivative described in (1) or its agricultural application Allowable salt as an active ingredient.

(3)如前述(2)所述之農藥組成物，其中，農藥組成物更含有界面活性劑。 (3) The pesticide composition as described in (2) above, wherein the pesticide composition further contains a surfactant.

(4)一種有害生物防除劑，該有害生物防除劑係含有前述(1)所述之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物或其農業上所容許之鹽作為活性成分。 (4) A pest control agent containing the 3-(1H-1,2,4-triazol-1-yl)benzamide derivative or its agriculture described in (1) above The salts allowed above are used as active ingredients.

(5)如前述(4)所述之有害生物防除劑，其中，有害生物防除劑為殺蟲劑、殺線蟲劑及殺蟎劑。 (5) The pest control agent as described in (4) above, wherein the pest control agent is an insecticide, nematicide and acaricide.

(6)如前述(5)所述之有害生物防除劑，該有害生物防除劑係對於栽培農園藝用植物之水田、田地、草地、果樹園、非農耕地、溫室、育苗設施、植物工廠中的有害生物具有防除效力。 (6) The pest control agent as described in (5) above, which is used in paddy fields, fields, grasslands, orchards, non-agricultural land, greenhouses, nursery facilities, and plant factories for cultivating agricultural and horticultural plants Of harmful organisms have the control effect.

(7)如前述(6)所述之有害生物防除劑，其中，農園藝用植物是藉由育種法或基因重組技術而被賦有抗性之植物。 (7) The pest control agent according to (6) above, wherein the plant for agricultural and horticultural purposes is a plant imparted with resistance by breeding methods or genetic recombination techniques.

(8)一種有害生物的防除方法，該防除方法係使用前述(1)所述之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物或其農業上所容許之鹽的有效成分量。 (8) A pest control method using the 3-(1H-1,2,4-triazol-1-yl)benzamide derivative described in (1) or its agricultural application Allowable amount of active ingredient in salt.

(9)一種有害生物的防除方法，該防除方法係將含有前述(1)所述之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物或其農業上所容許之鹽作為有效成分之農藥組成物，同時或分批地作用於農園藝用作物或是欲生育或正在生育農園藝用作物之場所來進行。 (9) A method for controlling harmful organisms, which comprises the 3-(1H-1,2,4-triazol-1-yl)benzamide derivative or its agriculture The pesticide composition with the salt allowed as an active ingredient can act on agricultural or horticultural uses or batches of places where agricultural or horticultural uses are to be produced or are being carried out simultaneously or in batches.

(10)如前述(8)或(9)所述之有害生物的防除方法，其中，施用有害生物防除劑之場所為水田、田地、草地、果樹園、非農耕地、溫室、育苗設施、植物工廠。 (10) The pest control method as described in (8) or (9) above, wherein the place where the pest control agent is applied is a paddy field, field, grassland, orchard, non-agricultural land, greenhouse, nursery facility, plant factory.

(11)如前述(8)至(10)中任一項所述之有害生物的防除方法，其中，將前述(1)所述之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物或其農業上所容許之鹽使用為殺蟲劑、殺線蟲劑及殺蟎劑。 (11) The pest control method according to any one of (8) to (10) above, wherein the 3-(1H-1,2,4-triazole-1 described in (1) above is used -Base) benzamide derivatives or their agriculturally acceptable salts are used as insecticides, nematicides and acaricides.

(12)一種有害生物防除劑的使用方法，該使用方法係將前述(4)至(7)中任一項所述之有害生物防除劑使用在對農園藝用作物之有害生物的防除。 (12) A method for using a pest control agent using the pest control agent described in any one of (4) to (7) above for the control of pests for agricultural and horticultural use.

(13)一種下述通式[II]表示之3-(1H-1,2,4-***-1-基)苯甲酸衍生物或其鹽， (13) A 3-(1H-1,2,4-triazol-1-yl)benzoic acid derivative or its salt represented by the following general formula [II],

Figure 108129126-A0202-12-0012-210
Figure 108129126-A0202-12-0012-210

式中， In the formula,

K表示-OH、C1至C6烷氧基、C1至C6鹵烷氧基、苯基氧基或是無取代或經(Z)p1取代之苯基C1至C6烷氧基， K represents -OH, C 1 to C 6 alkoxy, C 1 to C 6 haloalkoxy, phenyloxy or unsubstituted or substituted with (Z)p 1 phenyl C 1 to C 6 alkoxy base,

R3表示鹵素原子、氰基、C1至C6烷基、C1至C6鹵烷基、C1至C6烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、-NH2、-N(R9)R10、-C(=O)NH2或-C(=S)NH2， R 3 represents a halogen atom, cyano group, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, C 1 to C 6 alkoxy group, C 1 to C 6 alkylthio group, C 1 to C 6 Alkylsulfinyl, C 1 to C 6 alkylsulfonyl, -NH 2 , -N(R 9 )R 10 , -C(=O)NH 2 or -C(=S)NH 2 ,

n表示0至3的整數， n represents an integer from 0 to 3,

R4表示鹵素原子、氰基、硝基、C1至C6烷基、C1至C6烷氧基C1至C6烷基、C1至C6烷基硫C1至C6烷基、氰基C1至C6烷基、C1至C6鹵烷 基、C3至C6環烷基、C3至C6鹵環烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、-OH、C1至C6烷氧基、C1至C6鹵烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、-NH2或-N(R9)R10， R 4 represents a halogen atom, cyano group, nitro group, C 1 to C 6 alkyl group, C 1 to C 6 alkoxy group C 1 to C 6 alkyl group, C 1 to C 6 alkyl sulfur C 1 to C 6 alkyl group Group, cyano C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, C 2 to C 6 alkenyl, C 2 To C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, -OH, C 1 to C 6 alkoxy, C 1 to C 6 haloalkoxy, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfinyl, C 1 to C 6 haloalkylthio, C 1 to C 6 haloalkylsulfinyl Acyl, C 1 to C 6 haloalkylsulfonyl, -NH 2 or -N(R 9 )R 10 ,

R5表示氫原子、鹵素原子、氰基、硝基、C1至C6烷基、C1至C6鹵烷基、經R13任意地取代之C1至C6烷基、經R13任意地取代之C1至C6鹵烷基、C3至C6環烷基、C3至C6鹵環烷基、經R8任意地取代之C3至C6環烷基、C2至C6烯基、C2至C6鹵烯基、經R13任意地取代之C2至C6烯基、C2至C6炔基、C2至C6鹵炔基、經R13任意地取代之C2至C6炔基、-OH、-OS(=O)2R14、-OSi(R14)2R12、C1至C6烷氧基、C1至C6鹵烷氧基、經R13任意地取代之C1至C6烷氧基、經R13任意地取代之C1至C6鹵烷氧基、C2至C6烯基氧基、C2至C6鹵烯基氧基、C2至C6炔基氧基、C2至C6鹵炔基氧基、C3至C6環烷基氧基、C3至C6鹵環烷基氧基、無取代或經(Z)p1取代之苯基氧基、芳香族雜環氧基、飽和雜環氧基、-SH、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、經R13任意地取代之C1至C6烷基硫基、經R13任意地取代之C1至C6烷基亞磺醯基、經R13任意地取代之C1至C6烷基磺醯基、經R13任意地取代之C1至C6鹵烷基硫基、經R13任意地取代之C1至C6鹵烷基亞磺醯基、經R13任意地取代之C1至C6鹵烷基磺醯基、C2至C6烯基硫基、C2至C6烯基亞磺醯基、C2至C6烯基磺醯基、C2至C6鹵烯基硫基、C2至C6鹵烯基亞磺醯基、C2至C6鹵烯基磺 醯基、C2至C6炔基硫基、C2至C6炔基亞磺醯基、C2至C6炔基磺醯基、C3至C6環烷基硫基、C3至C6環烷基亞磺醯基、C3至C6環烷基磺醯基、無取代或經(Z)p1取代之苯基硫基、無取代或經(Z)p1取代之苯基亞磺醯基、無取代或經(Z)p1取代之苯基磺醯基、芳香族雜環硫基、芳香族雜環亞磺醯基、芳香族雜環磺醯基、飽和雜環硫基、飽和雜環亞磺醯基、飽和雜環磺醯基、-NH2、-N(R12)R14、-N(R10)C(=O)H、-N(R10)C(=O)R14、-N(R10)C(=O)OR14、-N(R10)C(=O)NH2、-N(R10)C(=O)N(R12)R14、-N(R10)C(=O)N(R12)OR14、-N(R10)C(=S)NH2、-N(R10)C(=S)N(R12)R14、-N(R10)S(=O)2R14、-N(R10)S(=O)2NH2、-N(R10)S(=O)2N(R12)R14、-C(=O)H、-C(=O)R14、-C(=O)NH2、-C(=O)N(R12)R14、-C(=O)N(R12)OR14、-C(R15)=NOH或-C(R15)=NOR14， R 5 represents a hydrogen atom, a halogen atom, cyano, nitro, C 1 to C 6 -alkyl, C 1 to C 6 haloalkyl, optionally substituted with R of C 13 1 to C 6 alkyl, R 13 the optionally substituted with a C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, optionally substituted with R of C 8 3 to C 6 cycloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl group, with R optionally substituted with of C 13 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, by R 13 Optionally substituted C 2 to C 6 alkynyl, -OH, -OS(=O) 2 R 14 , -OSi(R 14 ) 2 R 12 , C 1 to C 6 alkoxy, C 1 to C 6 halo alkoxy, optionally substituted by R of C 13 1 to C 6 alkoxy, optionally substituted by R of C 13 1 to C 6 haloalkoxy, C 2 to C 6 alkenyloxy, C 2 to C 6 haloalkenyloxy, C 2 to C 6 alkynyloxy, C 2 to C 6 haloalkynyloxy, C 3 to C 6 cycloalkyloxy, C 3 to C 6 halocycloalkyloxy Group, unsubstituted or substituted (Z)p 1 phenyloxy, aromatic heterocyclic oxy, saturated heterocyclic oxy, -SH, C 1 to C 6 alkylthio, C 1 to C 6 alkyl Sulfenyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 haloalkylthio, C 1 to C 6 haloalkylsulfinyl, C 1 to C 6 haloalkylsulfonyl acyl, optionally substituted by R 13 of a C 1 to C 6 alkylthio, optionally substituted by R 13 of a C 1 to C 6 alkylsulfinyl acyl, optionally substituted by the R 13 C 1 to C 6 alkylsulfonyl group, optionally substituted by R 13 of a C 1 to C 6 haloalkyl group, optionally substituted with R of C 13 1 to C 6 alkylsulfinyl halo acyl, optionally by R 13 Substituted C 1 to C 6 haloalkylsulfonyl, C 2 to C 6 alkenylsulfanyl, C 2 to C 6 alkenylsulfinyl, C 2 to C 6 alkenylsulfonyl, C 2 to C 6 haloalkenylthio, C 2 to C 6 haloalkenylsulfinyl, C 2 to C 6 haloalkenylsulfonyl, C 2 to C 6 alkynylthio, C 2 to C 6 alkynyl Sulfonyl, C 2 to C 6 alkynylsulfonyl, C 3 to C 6 cycloalkylsulfanyl, C 3 to C 6 cycloalkylsulfinyl, C 3 to C 6 cycloalkylsulfonyl Group, unsubstituted or substituted with (Z)p 1 phenylthio, unsubstituted or substituted with (Z)p 1 phenylsulfinyl, unsubstituted or substituted with (Z)p 1 phenylsulfonyl Acyl, aromatic heterocyclic sulfide, aromatic heterocyclic sulfenyl, aromatic heterocyclic sulfonyl, saturated heterocyclic sulfide, saturated heterocyclic sulfenyl, saturated heterocyclic sulfonyl, -NH 2 , -N(R 12 )R 14 , -N(R 10 )C(=O)H, -N(R 10 )C(=O)R 14 , -N(R 1 0 )C(=O)OR 14 , -N(R 10 )C(=O)NH 2 , -N(R 10 )C(=O)N(R 12 )R 14 , -N(R 10 )C (=O)N(R 12 )OR 14 , -N(R 10 )C(=S)NH 2 , -N(R 10 )C(=S)N(R 12 )R 14 , -N(R 10 )S(=O) 2 R 14 , -N(R 10 )S(=O) 2 NH 2 , -N(R 10 )S(=O) 2 N(R 12 )R 14 , -C(=O )H, -C(=O)R 14 , -C(=O)NH 2 , -C(=O)N(R 12 )R 14 , -C(=O)N(R 12 )OR 14 ,- C(R 15 )=NOH or -C(R 15 )=NOR 14 ,

R6表示氫原子、鹵素原子、氰基、硝基、C1至C6烷基、C1至C6鹵烷基、經R7任意地取代之C1至C6烷基、C3至C6環烷基、C3至C6鹵環烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、-OH、C1至C6烷氧基、C1至C6鹵烷氧基、經R7任意地取代之C1至C6烷氧基、C2至C6烯基氧基、C2至C6鹵烯基氧基、C2至C6炔基氧基、C2至C6鹵炔基氧基、C3至C6環烷基氧基、C3至C6鹵環烷基氧基、-SH、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、C2至C6烯基硫基、C2至C6烯基亞磺醯基、C2至C6烯基磺醯基、C2至C6炔基硫基、C2至C6炔基亞磺醯基、C2至C6炔基磺醯基、C3至C6環烷基硫基、C3至C6環烷基亞磺醯基、C3至C6環烷基磺醯基、-NH2、-N(R12)R14、-N(R10)C(=O)H、 -N(R10)C(=O)R14、-N(R10)C(=O)OR14、-N(R10)C(=O)NH2、-N(R10)C(=O)N(R12)R14、-N(R10)C(=O)N(R12)OR14、-N(R10)C(=S)NH2、-N(R10)C(=S)N(R12)R14、-N(R10)S(=O)2R14、-N(R10)S(=O)2NH2、-N(R10)S(=O)2N(R12)R14、-N=C(R12)R14、-N=C(R15)N(R12)R14、-NHC(R15)=NOR14、-N=S(R14)R12、-N=S(=O)(R14)R12、-N(R10)NH2、-N(R10)N(R12)R14、-N(R10)N(R10)C(=O)H、-N(R10)N(R10)C(=O)R14、-N(R10)N(R10)C(=O)OR14、-N(R10)N(R10)S(=O)2R14、-C(=O)H、-C(=O)R14、-C(R15)=NOH、-C(R15)=NOR14、-C(=O)NH2或-C(=O)N(R12)R11， R 6 represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a C 1 to C 6 alkyl group optionally substituted by R 7 , a C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, -OH, a C 1 to C 6 alkoxy group, C 1 to C 6 haloalkoxy, optionally substituted by R 7 of a C 1 to C 6 alkoxy, C 2 to C 6 alkenyloxy, C 2 To C 6 haloalkenyloxy, C 2 to C 6 alkynyloxy, C 2 to C 6 haloalkynyloxy, C 3 to C 6 cycloalkyloxy, C 3 to C 6 halocycloalkyl Oxygen, -SH, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 haloalkylthio, C 1 to C 6 haloalkylsulfinyl, C 1 to C 6 haloalkylsulfonyl, C 2 to C 6 alkenylthio, C 2 to C 6 alkenylsulfinyl, C 2 to C 6 alkenylsulfonyl, C 2 to C 6 alkynylsulfanyl, C 2 to C 6 alkynylsulfinyl, C 2 to C 6 alkynylsulfonyl, C 3 to C 6 cycloalkylsulfide Group, C 3 to C 6 cycloalkylsulfinyl, C 3 to C 6 cycloalkylsulfonyl, -NH 2 , -N(R 12 )R 14 , -N(R 10 )C(=O )H, -N(R 10 )C(=O)R 14 , -N(R 10 )C(=O)OR 14 , -N(R 10 )C(=O)NH 2 , -N(R 10 )C(=O)N(R 12 )R 14 , -N(R 10 )C(=O)N(R 12 )OR 14 , -N(R 10 )C(=S)NH 2 , -N( R 10 )C(=S)N(R 12 )R 14 , -N(R 10 )S(=O) 2 R 14 , -N(R 10 )S(=O) 2 NH 2 , -N(R 10 )S(=O) 2 N(R 12 )R 14 , -N=C(R 12 )R 14 , -N=C(R 15 )N(R 12 )R 14 , -NHC(R 15 )= NOR 14 , -N=S(R 14 )R 12 , -N=S(=O)(R 14 )R 12 , -N(R 10 )NH 2 , -N(R 10 )N(R 12 )R 14 , -N(R 10 )N(R 10 )C(=O)H, -N(R 10 )N(R 10 )C(=O)R 14 , -N(R 10 )N(R 10 ) C(=O)OR 14 , -N(R 10 )N(R 10 )S(=O) 2 R 14 , -C(=O)H, -C(= O)R 14 , -C(R 15 )=NOH, -C(R 15 )=NOR 14 , -C(=O)NH 2 or -C(=O)N(R 12 )R 11 ,

R7表示氰基、C3至C6環烷基、C3至C6鹵環烷基、-OH、C1至C6烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、-C(=O)NH2或-C(=O)N(R12)R11， R 7 represents cyano, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, -OH, C 1 to C 6 alkoxy, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, -C(=O)NH 2 or -C(=O)N(R 12 )R 11 ,

R8表示氰基、C1至C6烷基、C1至C6鹵烷基、C3至C6環烷基、C3至C6鹵環烷基、-C(=O)NH2或-C(=O)N(R12)R11， R 8 represents cyano, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, -C(=O)NH 2 Or -C(=O)N(R 12 )R 11 ,

R9表示C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6炔基、C3至C6環烷基、-C(=O)H、-C(=O)R11、-C(=O)OR11、-C(=O)NH2、-C(=O)N(R12)R11或-S(=O)2R11， R 9 represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 3 to C 6 cycloalkyl, -C(=O )H, -C(=O)R 11 , -C(=O)OR 11 , -C(=O)NH 2 , -C(=O)N(R 12 )R 11 or -S(=O) 2 R 11 ,

R10表示氫原子、C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6炔基、C3至C6環烷基、-C(=O)R11、-C(=O)OR11或-S(=O)2R11，或是R9及R10可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 10 represents a hydrogen atom, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 3 to C 6 cycloalkyl, -C (=O)R 11 , -C(=O)OR 11 or -S(=O) 2 R 11 , or R 9 and R 10 may be bonded to each other to form a C 2 to C 6 alkylene bond, At this time, the alkylene bond may contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond may be mono- or multi-substituted by a halogen atom or a C 1 to C 6 alkyl group,

R11表示C1至C6烷基、C1至C6鹵烷基、C1至C6烷氧基C1至C6烷基、C1至C6烷基硫C1至C6烷基、氰基C1至C6烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基或C3至C6鹵環烷基， R 11 represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy C 1 to C 6 alkyl, C 1 to C 6 alkyl sulfur C 1 to C 6 alkyl Group, cyano C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl or C 3 to C 6 halocycloalkyl,

R12表示氫原子、氰基、C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基或C3至C6鹵環烷基，或是R11及R12可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 12 represents a hydrogen atom, cyano group, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, C 2 to C 6 alkenyl group, C 2 to C 6 haloalkenyl group, C 2 to C 6 alkynyl group , C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl or C 3 to C 6 halocycloalkyl, or R 11 and R 12 may be bonded to each other to form C 2 to C 6 alkylene Base bond, this alkylene bond may contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond may be mono-substituted by halogen atom or C 1 to C 6 alkyl group or Replace more,

R13表示氰基、C3至C6環烷基、C3至C6鹵環烷基、-OH、-OR14、-OS(=O)2R14、-OSi(R14)2R12、-SH、-SR14、-S(=O)R14、-S(=O)2R14、-S(=O)2N(R12)R14、-NH2、-N(R12)R14、-N(R10)C(=O)H、-N(R10)C(=O)R14、-N(R10)C(=O)OR14、-N(R10)C(=O)NH2、-N(R10)C(=O)N(R12)R14、-N(R10)C(=O)N(R12)OR14、-N(R10)C(=S)NH2、-N(R10)C(=S)N(R12)R14、-N(R10)S(=O)2R14、-N(R10)S(=O)2NH2、-N(R10)S(=O)2N(R12)R14、-C(=O)H、-C(=O)R14、-C(=O)NH2、-C(=O)N(R12)R14、-C(=S)NH2、-C(=S)N(R12)R14、-C(R15)=NOH、-C(R15)=NOR14、-Si(R14)2R12、無取代或經(Z)p1取代之苯基、芳香族雜環或飽和雜環， R 13 represents cyano, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, -OH, -OR 14 , -OS(=O) 2 R 14 , -OSi(R 14 ) 2 R 12 , -SH, -SR 14 , -S(=O)R 14 , -S(=O) 2 R 14 , -S(=O) 2 N(R 12 )R 14 , -NH 2 , -N( R 12 )R 14 , -N(R 10 )C(=O)H, -N(R 10 )C(=O)R 14 , -N(R 10 )C(=O)OR 14 , -N( R 10 )C(=O)NH 2 , -N(R 10 )C(=O)N(R 12 )R 14 , -N(R 10 )C(=O)N(R 12 )OR 14 ,- N(R 10 )C(=S)NH 2 , -N(R 10 )C(=S)N(R 12 )R 14 , -N(R 10 )S(=O) 2 R 14 , -N( R 10 )S(=O) 2 NH 2 , -N(R 10 )S(=O) 2 N(R 12 )R 14 , -C(=O)H, -C(=O)R 14 ,- C(=O)NH 2 , -C(=O)N(R 12 )R 14 , -C(=S)NH 2 , -C(=S)N(R 12 )R 14 , -C(R 15 )=NOH, -C(R 15 )=NOR 14 , -Si(R 14 ) 2 R 12 , unsubstituted or substituted (Z)p 1 phenyl, aromatic heterocycle or saturated heterocycle,

R14表示C1至C6烷基、C1至C6鹵烷基、C1至C6烷氧基C1至C6烷基、C1至C6烷基硫C1至C6烷基、氰基C1至C6烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基、C3至C6鹵環烷基、無取代或經(Z)p1取代之苯基、無取代或經(Z)p1取代之苯基C1 至C6烷基、芳香族雜環、芳香族雜環C1至C6烷基、飽和雜環或飽和雜環C1至C6烷基，或是R12及R14可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 14 represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy C 1 to C 6 alkyl, C 1 to C 6 alkyl sulfur C 1 to C 6 alkyl Group, cyano C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, unsubstituted or substituted with (Z)p 1 phenyl, unsubstituted or substituted with (Z)p 1 phenyl C 1 to C 6 alkyl, Aromatic heterocycle, aromatic heterocycle C 1 to C 6 alkyl, saturated heterocycle or saturated heterocycle C 1 to C 6 alkyl, or R 12 and R 14 may be bonded to each other to form C 2 to C 6 alkylene bond, in which case the alkylene bond can contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond can be performed by a halogen atom or a C 1 to C 6 alkyl group Single or multiple substitution,

R15表示氫原子、鹵素原子、-NH2、氰基、C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基或C3至C6鹵環烷基，或是R14及R15可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 15 represents a hydrogen atom, a halogen atom, -NH 2 , cyano, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl or C 3 to C 6 halocycloalkyl, or R 14 and R 15 may be bonded to each other to form C 2 to C 6 alkylene bond, in which case the alkylene bond can contain 1 oxygen atom, sulfur atom or nitrogen atom, and C 2 to C 6 alkylene bond can be through halogen atom or C 1 to C 6 alkyl groups are mono- or poly-substituted,

Z表示鹵素原子、氰基、硝基、C1至C6烷基、C1至C6鹵烷基、-OH、C1至C6烷氧基、C1至C6鹵烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、-NH2、單(C1至C6烷基)胺基、二(C1至C6烷基)胺基、C1至C6烷基羰基胺基、N-(C1至C6烷基羰基)-N-(C1至C6烷基)胺基、C1至C6烷氧基羰基胺基、N-(C1至C6烷氧基羰基)-N-(C1至C6烷基)胺基、C1至C6烷基磺醯基胺基、N-(C1至C6烷基磺醯基)-N-(C1至C6烷基)胺基、C1至C6鹵烷基磺醯基胺基、N-(C1至C6鹵烷基磺醯基)-N-(C1至C6烷基)胺基、-C(=O)NH2、單(C1至C6烷基)胺基羰基、二(C1至C6烷基)胺基羰基、單(C1至C6鹵烷基)胺基羰基或苯基， Z represents halogen atom, cyano group, nitro group, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, -OH, C 1 to C 6 alkoxy group, C 1 to C 6 haloalkoxy group, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 haloalkylthio, C 1 to C 6 halo Alkylsulfinyl, C 1 to C 6 haloalkylsulfonyl, -NH 2 , mono(C 1 to C 6 alkyl)amino, di(C 1 to C 6 alkyl)amino, C 1 to C 6 alkylcarbonylamino, N-(C 1 to C 6 alkylcarbonyl)-N-(C 1 to C 6 alkyl)amino, C 1 to C 6 alkoxycarbonylamino, N -(C 1 to C 6 alkoxycarbonyl)-N-(C 1 to C 6 alkyl)amino, C 1 to C 6 alkylsulfonylamino, N-(C 1 to C 6 alkyl) Sulfonyl)-N-(C 1 to C 6 alkyl)amino, C 1 to C 6 haloalkylsulfonylamino, N-(C 1 to C 6 haloalkylsulfonyl)-N -(C 1 to C 6 alkyl)amino, -C(=O)NH 2 , mono(C 1 to C 6 alkyl)aminocarbonyl, di(C 1 to C 6 alkyl)aminocarbonyl, Mono(C 1 to C 6 haloalkyl)aminocarbonyl or phenyl,

芳香族雜環表示下列者， Aromatic heterocycle means the following,

Figure 108129126-A0202-12-0018-211
Figure 108129126-A0202-12-0018-211

飽和雜環表示下列者， Saturated heterocycle means the following,

Figure 108129126-A0202-12-0018-212
Figure 108129126-A0202-12-0018-212

p1表示0至5的整數， p 1 represents an integer from 0 to 5,

p2表示0至4的整數， p 2 represents an integer from 0 to 4,

p3表示0至3的整數， p 3 represents an integer from 0 to 3,

p4表示0至2的整數， p 4 represents an integer from 0 to 2,

t表示0或1的整數。 t represents an integer of 0 or 1.

(14)一種下述通式[III]表示之1-苯基-1H-1,2,4-***衍生物或其鹽， (14) A 1-phenyl-1H-1,2,4-triazole derivative represented by the following general formula [III] or a salt thereof,

Figure 108129126-A0202-12-0018-213
Figure 108129126-A0202-12-0018-213

式中， In the formula,

W表示氫原子、鹵素原子或氰基， W represents a hydrogen atom, a halogen atom or a cyano group,

R3表示鹵素原子、氰基、C1至C6烷基、C1至C6鹵烷基、C1至C6烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、-NH2、-N(R9)R10、-C(=O)NH2或-C(=S)NH2， R 3 represents a halogen atom, cyano group, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, C 1 to C 6 alkoxy group, C 1 to C 6 alkylthio group, C 1 to C 6 Alkylsulfinyl, C 1 to C 6 alkylsulfonyl, -NH 2 , -N(R 9 )R 10 , -C(=O)NH 2 or -C(=S)NH 2 ,

n表示0至3的整數， n represents an integer from 0 to 3,

R4表示鹵素原子、氰基、硝基、C1至C6烷基、C1至C6烷氧基C1至C6烷基、C1至C6烷基硫C1至C6烷基、氰基C1至C6烷基、C1至C6鹵烷基、C3至C6環烷基、C3至C6鹵環烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、-OH、C1至C6烷氧基、C1至C6鹵烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、-NH2或-N(R9)R10， R 4 represents a halogen atom, cyano group, nitro group, C 1 to C 6 alkyl group, C 1 to C 6 alkoxy group C 1 to C 6 alkyl group, C 1 to C 6 alkyl sulfur C 1 to C 6 alkyl group Group, cyano C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, C 2 to C 6 alkenyl, C 2 To C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, -OH, C 1 to C 6 alkoxy, C 1 to C 6 haloalkoxy, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfinyl, C 1 to C 6 haloalkylthio, C 1 to C 6 haloalkylsulfinyl Acyl, C 1 to C 6 haloalkylsulfonyl, -NH 2 or -N(R 9 )R 10 ,

R5表示氫原子、鹵素原子、氰基、硝基、C1至C6烷基、C1至C6鹵烷基、經R13任意地取代之C1至C6烷基、經R13任意地取代之C1至C6鹵烷基、C3至C6環烷基、C3至C6鹵環烷基、經R8任意地取代之C3至C6環烷基、C2至C6烯基、C2至C6鹵烯基、經R13任意地取代之C2至C6烯基、C2至C6炔基、C2至C6鹵炔基、經R13任意地取代之C2至C6炔基、-OH、-OC(=O)R14、-OS(=O)2R14、-OSi(R14)2R12、C1至C6烷氧基、C1至C6鹵烷氧基、經R13任意地取代之C1至C6烷氧基、經R13任意地取代之C1至C6鹵烷氧基、C2至C6烯基氧基、C2至C6鹵烯基氧基、C2至C6炔基氧基、C2至C6鹵炔基氧基、C3至C6環烷基氧基、C3至C6鹵環烷基氧基、無取代或經(Z)p1取代之苯基氧基、芳香族雜環氧基、飽和雜環氧基、-SH、C1 至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、經R13任意地取代之C1至C6烷基硫基、經R13任意地取代之C1至C6烷基亞磺醯基、經R13任意地取代之C1至C6烷基磺醯基、經R13任意地取代之C1至C6鹵烷基硫基、經R13任意地取代之C1至C6鹵烷基亞磺醯基、經R13任意地取代之C1至C6鹵烷基磺醯基、C2至C6烯基硫基、C2至C6烯基亞磺醯基、C2至C6烯基磺醯基、C2至C6鹵烯基硫基、C2至C6鹵烯基亞磺醯基、C2至C6鹵烯基磺醯基、C2至C6炔基硫基、C2至C6炔基亞磺醯基、C2至C6炔基磺醯基、C3至C6環烷基硫基、C3至C6環烷基亞磺醯基、C3至C6環烷基磺醯基、無取代或經(Z)p1取代之苯基硫基、無取代或經(Z)p1取代之苯基亞磺醯基、無取代或經(Z)p1取代之苯基磺醯基、芳香族雜環硫基、芳香族雜環亞磺醯基、芳香族雜環磺醯基、飽和雜環硫基、飽和雜環亞磺醯基、飽和雜環磺醯基、-NH2、-N(R12)R14、-N(R10)C(=O)H、-N(R10)C(=O)R14、-N(R10)C(=O)OR14、-N(R10)C(=O)NH2、-N(R10)C(=O)N(R12)R14、-N(R10)C(=O)N(R12)OR14、-N(R10)C(=S)NH2、-N(R10)C(=S)N(R12)R14、-N(R10)S(=O)2R14、-N(R10)S(=O)2NH2、-N(R10)S(=O)2N(R12)R14、-C(=O)H、-C(=O)R14、-C(=O)OH、-C(=O)OR14、-C(=O)NH2、-C(=O)N(R12)R14、-C(=O)N(R12)OR14、-C(R15)=NOH或-C(R15)=NOR14， R 5 represents a hydrogen atom, a halogen atom, cyano, nitro, C 1 to C 6 -alkyl, C 1 to C 6 haloalkyl, optionally substituted with R of C 13 1 to C 6 alkyl, R 13 the optionally substituted with a C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, optionally substituted with R of C 8 3 to C 6 cycloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl group, with R optionally substituted with of C 13 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, by R 13 Optionally substituted C 2 to C 6 alkynyl, -OH, -OC(=O)R 14 , -OS(=O) 2 R 14 , -OSi(R 14 ) 2 R 12 , C 1 to C 6 alkane group, C 1 to C 6 haloalkoxy, optionally substituted by R 13 of a C 1 to C 6 alkoxy, optionally substituted by R 13 of a C 1 to C 6 haloalkoxy, C 2 to C 6 alkenyloxy, C 2 to C 6 haloalkenyloxy, C 2 to C 6 alkynyloxy, C 2 to C 6 haloalkynyloxy, C 3 to C 6 cycloalkyloxy, C 3 to C 6 halocycloalkyloxy, unsubstituted or substituted (Z)p 1 phenyloxy, aromatic heterocyclic oxy, saturated heterocyclic oxy, -SH, C 1 to C 6 alkyl Thio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 haloalkylthio, C 1 to C 6 haloalkylsulfinyl, a C 1 to C 6 haloalkyl sulfo acyl, optionally substituted by R 13 of a C 1 to C 6 alkylthio, optionally substituted by R of C 13 1 to C 6 alkylsulfinyl acyl, with R 13 of optionally substituted a C 1 to C 6 alkylsulfonyl group, optionally substituted by R of C 13 1 to C 6 haloalkyl group, optionally substituted by R of C 13 1 to C 6 alkylsulfinyl halo Sulfonyl, C 1 to C 6 haloalkyl sulfonyl optionally substituted by R 13 , C 2 to C 6 alkenylthio, C 2 to C 6 alkenylsulfinyl, C 2 to C 6 Alkenylsulfonyl, C 2 to C 6 haloalkenylthio, C 2 to C 6 haloalkenylsulfinyl, C 2 to C 6 haloalkenylsulfonyl, C 2 to C 6 alkynylsulfide group, C 2 to C 6 alkynyl alkylsulfinyl acyl, C 2 to C 6 alkynyl group sulfo acyl, C 3 to C 6 cycloalkyl group, C 3 to C 6 cycloalkyl acyl alkylsulfinyl, C 3 to C 6 cycloalkylsulfonyl, unsubstituted or substituted with (Z)p 1 phenylthio, unsubstituted or substituted with (Z)p 1 phenylsulfinyl, unsubstituted or substituted ( Z) P 1 substituted phenylsulfonyl, aromatic heterocyclic sulfenyl, aromatic heterocyclic sulfenyl, aromatic heterocyclic sulfonyl, saturated heterocyclic sulfenyl, saturated heterocyclic sulfenyl, Saturated heterocyclic sulfonyl, -NH 2 , -N(R 12 )R 14 , -N(R 10 )C(=O)H, -N(R 10 )C(=O )R 14 , -N(R 10 )C(=O)OR 14 , -N(R 10 )C(=O)NH 2 , -N(R 10 )C(=O)N(R 12 )R 14 , -N(R 10 )C(=O)N(R 12 )OR 14 , -N(R 10 )C(=S)NH 2 , -N(R 10 )C(=S)N(R 12 ) R 14 , -N(R 10 )S(=O) 2 R 14 , -N(R 10 )S(=O) 2 NH 2 , -N(R 10 )S(=O) 2 N(R 12 ) R 14 , -C(=O)H, -C(=O)R 14 , -C(=O)OH, -C(=O)OR 14 , -C(=O)NH 2 , -C(= O)N(R 12 )R 14 , -C(=O)N(R 12 )OR 14 , -C(R 15 )=NOH or -C(R 15 )=NOR 14 ,

R6表示氫原子、鹵素原子、氰基、硝基、C1至C6烷基、C1至C6鹵烷基、經R7任意地取代之C1至C6烷基、C3至C6環烷基、C3至C6鹵環烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、-OH、C1至C6烷氧基、C1至C6鹵烷氧基、經R7任意地取代之C1至C6烷氧基、 C2至C6烯基氧基、C2至C6鹵烯基氧基、C2至C6炔基氧基、C2至C6鹵炔基氧基、C3至C6環烷基氧基、C3至C6鹵環烷基氧基、-SH、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、C2至C6烯基硫基、C2至C6烯基亞磺醯基、C2至C6烯基磺醯基、C2至C6炔基硫基、C2至C6炔基亞磺醯基、C2至C6炔基磺醯基、C3至C6環烷基硫基、C3至C6環烷基亞磺醯基、C3至C6環烷基磺醯基、-NH2、-N(R12)R14、-N(R10)C(=O)H、-N(R10)C(=O)R14、-N(R10)C(=O)OR14、-N(R10)C(=O)NH2、-N(R10)C(=O)N(R12)R14、-N(R10)C(=O)N(R12)OR14、-N(R10)C(=S)NH2、-N(R10)C(=S)N(R12)R14、-N(R10)S(=O)2R14、-N(R10)S(=O)2NH2、-N(R10)S(=O)2N(R12)R14、-N=C(R12)R14、-N=C(R15)N(R12)R14、-NHC(R15)=NOR14、-N=S(R14)R12、-N=S(=O)(R14)R12、-N(R10)NH2、-N(R10)N(R12)R14、-N(R10)N(R10)C(=O)H、-N(R10)N(R10)C(=O)R14、-N(R10)N(R10)C(=O)OR14、-N(R10)N(R10)S(=O)2R14、-C(=O)H、-C(=O)R14、-C(R15)=NOH、-C(R15)=NOR14、-C(=O)OH、-C(=O)OR14、-C(=O)NH2或-C(=O)N(R12)R11， R 6 represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a C 1 to C 6 alkyl group optionally substituted by R 7 , a C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, -OH, a C 1 to C 6 alkoxy group, C 1 to C 6 haloalkoxy, optionally substituted by R 7 of a C 1 to C 6 alkoxy, C 2 to C 6 alkenyloxy, C 2 To C 6 haloalkenyloxy, C 2 to C 6 alkynyloxy, C 2 to C 6 haloalkynyloxy, C 3 to C 6 cycloalkyloxy, C 3 to C 6 halocycloalkyl Oxygen, -SH, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 haloalkylthio, C 1 to C 6 haloalkylsulfinyl, C 1 to C 6 haloalkylsulfonyl, C 2 to C 6 alkenylthio, C 2 to C 6 alkenylsulfinyl, C 2 to C 6 alkenylsulfonyl, C 2 to C 6 alkynylsulfanyl, C 2 to C 6 alkynylsulfinyl, C 2 to C 6 alkynylsulfonyl, C 3 to C 6 cycloalkylsulfide Group, C 3 to C 6 cycloalkylsulfinyl, C 3 to C 6 cycloalkylsulfonyl, -NH 2 , -N(R 12 )R 14 , -N(R 10 )C(=O )H, -N(R 10 )C(=O)R 14 , -N(R 10 )C(=O)OR 14 , -N(R 10 )C(=O)NH 2 , -N(R 10 )C(=O)N(R 12 )R 14 , -N(R 10 )C(=O)N(R 12 )OR 14 , -N(R 10 )C(=S)NH 2 , -N( R 10 )C(=S)N(R 12 )R 14 , -N(R 10 )S(=O) 2 R 14 , -N(R 10 )S(=O) 2 NH 2 , -N(R 10 )S(=O) 2 N(R 12 )R 14 , -N=C(R 12 )R 14 , -N=C(R 15 )N(R 12 )R 14 , -NHC(R 15 )= NOR 14 , -N=S(R 14 )R 12 , -N=S(=O)(R 14 )R 12 , -N(R 10 )NH 2 , -N(R 10 )N(R 12 )R 14 , -N(R 10 )N(R 10 )C(=O)H, -N(R 10 )N(R 10 )C(=O)R 14 , -N(R 10 )N(R 10 ) C(=O)OR 14 , -N(R 10 )N(R 10 )S(=O) 2 R 14 , -C(=O)H, -C(= O)R 14 , -C(R 15 )=NOH, -C(R 15 )=NOR 14 , -C(=O)OH, -C(=O)OR 14 , -C(=O)NH 2 or -C(=O)N(R 12 )R 11 ,

R7表示氰基、C3至C6環烷基、C3至C6鹵環烷基、-OH、C1至C6烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、-C(=O)OH、-C(=O)OR11、-C(=O)NH2或-C(=O)N(R12)R11， R 7 represents cyano, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, -OH, C 1 to C 6 alkoxy, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, -C(=O)OH, -C(=O)OR 11 , -C(=O)NH 2 or -C(= O)N(R 12 )R 11 ,

R8表示氰基、C1至C6烷基、C1至C6鹵烷基、C3至C6環烷基、C3至C6鹵環烷基、-C(=O)OR11、-C(=O)NH2或-C(=O)N(R12)R11， R 8 represents cyano, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, -C(=O)OR 11 , -C(=O)NH 2 or -C(=O)N(R 12 )R 11 ,

R9表示C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6炔基、C3至C6環烷基、-C(=O)H、-C(=O)R11、-C(=O)OR11、-C(=O)NH2、-C(=O)N(R12)R11或-S(=O)2R11， R 9 represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 3 to C 6 cycloalkyl, -C(=O )H, -C(=O)R 11 , -C(=O)OR 11 , -C(=O)NH 2 , -C(=O)N(R 12 )R 11 or -S(=O) 2 R 11 ,

R10表示氫原子、C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6炔基、C3至C6環烷基、-C(=O)R11、-C(=O)OR11或-S(=O)2R11，或是R9及R10可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 10 represents a hydrogen atom, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 3 to C 6 cycloalkyl, -C (=O)R 11 , -C(=O)OR 11 or -S(=O) 2 R 11 , or R 9 and R 10 may be bonded to each other to form a C 2 to C 6 alkylene bond, At this time, the alkylene bond may contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond may be mono- or multi-substituted by a halogen atom or a C 1 to C 6 alkyl group,

R11表示C1至C6烷基、C1至C6鹵烷基、C1至C6烷氧基C1至C6烷基、C1至C6烷基硫C1至C6烷基、氰基C1至C6烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基或C3至C6鹵環烷基， R 11 represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy C 1 to C 6 alkyl, C 1 to C 6 alkyl sulfur C 1 to C 6 alkyl Group, cyano C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl or C 3 to C 6 halocycloalkyl,

R12表示氫原子、氰基、C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基或C3至C6鹵環烷基，或是R11及R12可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 12 represents a hydrogen atom, cyano group, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, C 2 to C 6 alkenyl group, C 2 to C 6 haloalkenyl group, C 2 to C 6 alkynyl group , C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl or C 3 to C 6 halocycloalkyl, or R 11 and R 12 may be bonded to each other to form C 2 to C 6 alkylene Base bond, this alkylene bond may contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond may be mono-substituted by halogen atom or C 1 to C 6 alkyl group or Replace more,

R13表示氰基、C3至C6環烷基、C3至C6鹵環烷基、-OH、-OR14、-OC(=O)R14、-OS(=O)2R14、-OSi(R14)2R12、-SH、-SR14、-S(=O)R14、-S(=O)2R14、-S(=O)2N(R12)R14、-NH2、-N(R12)R14、-N(R10)C(=O)H、-N(R10)C(=O)R14、-N(R10)C(=O)OR14、-N(R10)C(=O)NH2、-N(R10)C(=O)N(R12)R14、-N(R10)C(=O)N(R12)OR14、-N(R10)C(=S)NH2、-N(R10)C(=S)N (R12)R14、-N(R10)S(=O)2R14、-N(R10)S(=O)2NH2、-N(R10)S(=O)2N(R12)R14、-C(=O)H、-C(=O)R14、-C(=O)OH、-C(=O)OR14、-C(=O)NH2、-C(=O)N(R12)R14、-C(=S)NH2、-C(=S)N(R12)R14、-C(R15)=NOH、-C(R15)=NOR14、-Si(R14)2R12、無取代或經(Z)p1取代之苯基、芳香族雜環或飽和雜環， R 13 represents cyano, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, -OH, -OR 14 , -OC(=O)R 14 , -OS(=O) 2 R 14 , -OSi(R 14 ) 2 R 12 , -SH, -SR 14 , -S(=O)R 14 , -S(=O) 2 R 14 , -S(=O) 2 N(R 12 )R 14 , -NH 2 , -N(R 12 )R 14 , -N(R 10 )C(=O)H, -N(R 10 )C(=O)R 14 , -N(R 10 )C( =O)OR 14 , -N(R 10 )C(=O)NH 2 , -N(R 10 )C(=O)N(R 12 )R 14 , -N(R 10 )C(=O) N(R 12 )OR 14 , -N(R 10 )C(=S)NH 2 , -N(R 10 )C(=S)N (R 12 )R 14 , -N(R 10 )S(= O) 2 R 14 , -N(R 10 )S(=O) 2 NH 2 , -N(R 10 )S(=O) 2 N(R 12 )R 14 , -C(=O)H,- C(=O)R 14 , -C(=O)OH, -C(=O)OR 14 , -C(=O)NH 2 , -C(=O)N(R 12 )R 14 , -C (=S)NH 2 , -C(=S)N(R 12 )R 14 , -C(R 15 )=NOH, -C(R 15 )=NOR 14 , -Si(R 14 ) 2 R 12 , Unsubstituted or substituted (Z)p 1 phenyl, aromatic heterocyclic or saturated heterocyclic,

R14表示C1至C6烷基、C1至C6鹵烷基、C1至C6烷氧基C1至C6烷基、C1至C6烷基硫C1至C6烷基、氰基C1至C6烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基、C3至C6鹵環烷基、無取代或經(Z)p1取代之苯基、無取代或經(Z)p1取代之苯基C1至C6烷基、芳香族雜環、芳香族雜環C1至C6烷基、飽和雜環或飽和雜環C1至C6烷基，或是R12及R14可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 14 represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy C 1 to C 6 alkyl, C 1 to C 6 alkyl sulfur C 1 to C 6 alkyl Group, cyano C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, unsubstituted or substituted with (Z)p 1 phenyl, unsubstituted or substituted with (Z)p 1 phenyl C 1 to C 6 alkyl, Aromatic heterocycle, aromatic heterocycle C 1 to C 6 alkyl, saturated heterocycle or saturated heterocycle C 1 to C 6 alkyl, or R 12 and R 14 may be bonded to each other to form C 2 to C 6 alkylene bond, in which case the alkylene bond can contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond can be performed by a halogen atom or a C 1 to C 6 alkyl group Single or multiple substitution,

R15表示氫原子、鹵素原子、-NH2、氰基、C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基或C3至C6鹵環烷基，或是R14及R15可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 15 represents a hydrogen atom, a halogen atom, -NH 2 , cyano, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl or C 3 to C 6 halocycloalkyl, or R 14 and R 15 may be bonded to each other to form C 2 to C 6 alkylene bond, in which case the alkylene bond can contain 1 oxygen atom, sulfur atom or nitrogen atom, and C 2 to C 6 alkylene bond can be through halogen atom or C 1 to C 6 alkyl groups are mono- or poly-substituted,

Z表示鹵素原子、氰基、硝基、C1至C6烷基、C1至C6鹵烷基、-OH、C1至C6烷氧基、C1至C6鹵烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、-NH2、單(C1至C6烷基)胺基、二(C1至C6烷 基)胺基、C1至C6烷基羰基胺基、N-(C1至C6烷基羰基)-N-(C1至C6烷基)胺基、C1至C6烷氧基羰基胺基、N-(C1至C6烷氧基羰基)-N-(C1至C6烷基)胺基、C1至C6烷基磺醯基胺基、N-(C1至C6烷基磺醯基)-N-(C1至C6烷基)胺基、C1至C6鹵烷基磺醯基胺基、N-(C1至C6鹵烷基磺醯基)-N-(C1至C6烷基)胺基、-C(=O)NH2、單(C1至C6烷基)胺基羰基、二(C1至C6烷基)胺基羰基、單(C1至C6鹵烷基)胺基羰基或苯基， Z represents halogen atom, cyano group, nitro group, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, -OH, C 1 to C 6 alkoxy group, C 1 to C 6 haloalkoxy group, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 haloalkylthio, C 1 to C 6 halo Alkylsulfinyl, C 1 to C 6 haloalkylsulfonyl, -NH 2 , mono(C 1 to C 6 alkyl)amino, di(C 1 to C 6 alkyl)amino, C 1 to C 6 alkylcarbonylamino, N-(C 1 to C 6 alkylcarbonyl)-N-(C 1 to C 6 alkyl)amino, C 1 to C 6 alkoxycarbonylamino, N -(C 1 to C 6 alkoxycarbonyl)-N-(C 1 to C 6 alkyl)amino, C 1 to C 6 alkylsulfonylamino, N-(C 1 to C 6 alkyl) Sulfonyl)-N-(C 1 to C 6 alkyl)amino, C 1 to C 6 haloalkylsulfonylamino, N-(C 1 to C 6 haloalkylsulfonyl)-N -(C 1 to C 6 alkyl)amino, -C(=O)NH 2 , mono(C 1 to C 6 alkyl)aminocarbonyl, di(C 1 to C 6 alkyl)aminocarbonyl, Mono(C 1 to C 6 haloalkyl)aminocarbonyl or phenyl,

芳香族雜環表示下列者， Aromatic heterocycle means the following,

Figure 108129126-A0202-12-0024-214
Figure 108129126-A0202-12-0024-214

飽和雜環表示下列者， Saturated heterocycle means the following,

Figure 108129126-A0202-12-0024-215
Figure 108129126-A0202-12-0024-215

p1表示0至5的整數， p 1 represents an integer from 0 to 5,

p2表示0至4的整數， p 2 represents an integer from 0 to 4,

p3表示0至3的整數， p 3 represents an integer from 0 to 3,

p4表示0至2的整數， p 4 represents an integer from 0 to 2,

t表示0或1的整數。 t represents an integer of 0 or 1.

(15)一種前述(1)所述之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物的製造方法，該製造方法係以前述(14)所述之1-苯基-1H-1,2,4-***衍生物或其鹽作為原料。 (15) A method for producing a 3-(1H-1,2,4-triazol-1-yl) benzamide derivative described in (1) above, which is described in (14) above The 1-phenyl-1H-1,2,4-triazole derivative or its salt is used as a raw material.

本發明之通式[I]所表示之化合物係具有優異的有害生物防除作用，對於半翅目(Hemiptera)害蟲、鱗翅目(Lepidoptera)害蟲、鞘翅目(Coleoptera)害蟲、雙翅目(Diptera)害蟲、膜翅目(Hymenoptera)害蟲、直翅目(Orthoptera)害蟲、纓翅目(Thysanoptera)害蟲、葉蟎(Tetranychidae)類、植物寄生性線蟲類等廣範圍的有害生物顯示出優異防除效果，再者，亦可對具有抗藥劑性之有害生物進行防除。 The compound represented by the general formula [I] of the present invention has an excellent pest control effect against Hemiptera pests, Lepidoptera pests, Coleoptera pests, and Diptera pests. Pests, Hymenoptera pests, Orthoptera pests, Thysanoptera pests, Tetranychidae, Tetranychidae, plant parasitic nematodes and other pests show excellent control effect, In addition, it can also control pests that are resistant to chemicals.

尤其是，含有本發明之化合物之有害生物防除劑，對於以二點葉蟎(Tetranychus urticae Koch)、神澤氏葉蟎(Tetranychus kanzawai Kishida)、柑橘葉蟎(Panonychus citri)等為代表之葉蟎類；以褐飛蝨(Nilaparvata lugens stal)、偽黑尾葉蟬(Nephotettix cincticeps)、綿蚜(Aphis gossypii)等為代表之半翅目害蟲；以水稻水象鼻蟲(Lissorhoptrus oryzophilus Kuschel)、負泥蟲(Oulema oryzae)、豔金龜(Mimela splendens)等為代表之鞘翅目害蟲；根瘤線蟲(Meloidogyne incognita)等線蟲類；以及以小菜蛾(Plutella xylostella)、二化螟(Chilo suppressalis)、番茄夜蛾(Helicoverpa armigera)等為代表之鱗翅目害蟲係顯示出卓越成效。再者，由於滲透移動性優異，所以可實施以土壤處理進行之安全且省力的施用方法。 In particular, the pest control agent containing the compound of the present invention is suitable for spider mites represented by Tetranychus urticae Koch, Tetranychus kanzawai Kishida, Panonychus citri, etc. Classes: Hemiptera pests represented by brown planthopper (Nilaparvata lugens stal), pseudo black-tailed leafhopper (Nephotettix cincticeps), cotton aphid (Aphis gossypii), etc.; represented by rice water weevils (Lissorhoptrus oryzophilus Kuschel), negative mudworms (Oulema oryzae), Michela splendens and other coleoptera pests; nematodes such as Meloidogyne incognita; and Plutella xylostella, Chilo suppressalis, and Spodoptera exigua Helicoverpa armigera) and other Lepidoptera pests have shown excellent results. Furthermore, since it has excellent penetration mobility, it is possible to implement a safe and labor-saving application method by soil treatment.

以下說明本說明書中所記載之記號及用語。 The symbols and terms described in this manual are explained below.

於本發明中所謂「有害生物防除劑」意指於農園藝領域、家畜及寵物等動物、家庭用或防疫用的殺蟲劑、殺蟎劑、殺線蟲劑等。 In the present invention, the term "harmful organism control agent" means insecticides, acaricides, nematicides, etc. in the agricultural and horticultural fields, animals such as livestock and pets, household or epidemic prevention.

於本發明中所謂「鹵素原子」係表示氟原子、氯原子、溴原子、碘原子。 In the present invention, the "halogen atom" means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

於本發明中所謂「C1至C6」等標示意指接續元素符號之數字表示碳數，例如，在此情形中，表示碳數為1至6個的範圍中之任一個。 In the present invention, the so-called “C 1 to C 6 ”and other symbols indicate that the number of the successive element symbol represents the carbon number. For example, in this case, it represents any one of the carbon number in the range of 1 to 6.

於本發明中所謂「C1至C6烷基」在無特別限定下係表示碳數為1至6之直鏈或分枝鏈狀的烷基，可列舉例如：甲基、乙基、正丙基、異丙基、正丁基、第二丁基、異丁基、第三丁基、正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1-乙基丙基、1,1-二甲基丙基、1,2-二甲基丙基、新戊基、正己基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1-乙基丁基、2-乙基丁基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基或1-乙基-2-甲基丙基等基。 In the present invention, the "C 1 to C 6 alkyl group" means a straight or branched chain alkyl group having 1 to 6 carbon atoms, and examples thereof include methyl, ethyl, and n Propyl, isopropyl, n-butyl, second butyl, isobutyl, third butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3- Methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3- Dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1, Groups such as 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, or 1-ethyl-2-methylpropyl.

於本發明中所謂「C1至C6鹵烷基」在無特別限定下係表示經相同或相異之1至13個鹵素原子所取代之碳數為1至6之直鏈或分枝鏈狀的鹵烷基，可列舉例如：氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、溴甲基、二溴甲基、三溴甲基、碘甲基、氯二氟甲基、二氯氟甲基、1-氟乙基、2-氟乙基、1,1-二氟乙基、2,2-二氟乙基、2,2,2-三 氟乙基、1,1,2,2-四氟乙基、五氟乙基、1-氯乙基、2-氯乙基、1,1-二氯乙基、2,2-二氯乙基、2,2,2-三氯乙基、1,1,2,2-四氯乙基、五氯乙基、1-溴乙基、2-溴乙基、2,2,2-三溴乙基、1-碘乙基、2-碘乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2-三氯乙基、1-氟丙基、2-氟丙基、3-氟丙基、1,1-二氟丙基、2,2-二氟丙基、3,3-二氟丙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、七氟丙基、1-氟丙烷-2-基、2-氟丙烷-2-基、1,1-二氟丙烷-2-基、1,2-二氟丙烷-2-基、1,3-二氟丙烷-2-基、1,2,3-三氟丙烷-2-基、1,1,3,3-四氟丙烷-2-基、1,1,1,3,3,3-六氟丙烷-2-基、七氟丙烷-2-基、1-氯丙基、2-氯丙基、3-氯丙基、1,1-二氯丙基、2,2-二氯丙基、3,3-二氯丙基、3,3,3-三氯丙基、2,2,3,3,3-五氯丙基、七氯丙基、1-氯丙烷-2-基、2-氯丙烷-2-基、1,1-二氯丙烷-2-基、1,2-二氯丙烷-2-基、1,3-二氯丙烷-2-基、1,2,3-三氯丙烷-2-基、1,1,3,3-四氯丙烷-2-基、1,1,1,3,3,3-六氯丙烷-2-基、七氯丙烷-2-基、1-溴丙基、2-溴丙基、3-溴丙基、1-溴丙烷-2-基、2-溴丙烷-2-基、1-碘丙基、2-碘丙基、3-碘丙基、1-碘丙烷-2-基、2-碘丙烷-2-基、1-氟丁基、2-氟丁基、3-氟丁基、4-氟丁基、4,4-二氟丁基、4,4,4-三氟丁基、3,3,4,4,4-五氟丁基、2,2,3,3,4,4,4-七氟丁基、九氟丁基、1,1,1-三氟丁烷-2-基、4,4,4-三氟丁烷-2-基、3,3,4,4,4-五氟丁烷-2-基、九氟丁烷-2-基、1,1,1,3,3,3-六氟-2-(三氟甲基)丙烷-2-基、1-氯丁基、2-氯丁基、3-氯丁基、4-氯丁基、4,4-二氯丁基、4,4,4-三氯丁基、九氯丁基、1,1,1-三氯丁烷-2-基、4,4,4-三氯丁烷-2-基、九氯丁烷-2-基、1-溴丁基、2-溴丁基、3-溴丁基、4-溴丁基、1-碘丁基、2-碘丁基、3-碘丁基、4-碘丁基、4-氯-1,1,2,2,3,3,4,4-八氟丁基、4-溴-1,1,2,2,3,3,4,4-八氟丁基、1-氟戊基、2-氟戊基、3-氟戊基、4-氟戊基、 5-氟戊基、5,5,5-三氟戊基、4,4,5,5,5-五氟戊基、3,3,4,4,5,5,5-七氟戊基、2,2,3,3,4,4,5,5,5-九氟戊基、十一氟戊基、1-氯戊基、2-氯戊基、3-氯戊基、4-氯戊基、5-氯戊基、5,5,5-三氯戊基、4,4,5,5,5-五氯戊基、3,3,4,4,5,5,5-七氯戊基、2,2,3,3,4,4,5,5,5-九氯戊基、十一氯戊基、1-溴戊基、2-溴戊基、3-溴戊基、4-溴戊基、5-溴戊基、5-碘戊基、1-氟己基、2-氟己基、3-氟己基、4-氟己基、5-氟己基、6-氟己基、6,6,6-三氟己基、5,5,6,6,6-五氟己基、4,4,5,5,6,6,6-七氟己基、3,3,4,4,5,5,6,6,6-九氟己基、2,2,3,3,4,4,5,5,6,6,6-十一氟己基、十三氟己基、1-氯己基、2-氯己基、3-氯己基、4-氯己基、5-氯己基、6-氯己基、5-溴己基、6-溴己基、5-碘己基或6-碘己基等基。 In the present invention, the so-called "C 1 to C 6 haloalkyl group" means a straight or branched chain with 1 to 6 carbon atoms substituted by the same or different 1 to 13 halogen atoms, unless otherwise specified. Examples of haloalkyl groups include fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl Group, iodomethyl, chlorodifluoromethyl, dichlorofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2, 2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 1-chloroethyl, 2-chloroethyl, 1,1-dichloroethyl, 2, 2-dichloroethyl, 2,2,2-trichloroethyl, 1,1,2,2-tetrachloroethyl, pentachloroethyl, 1-bromoethyl, 2-bromoethyl, 2, 2,2-tribromoethyl, 1-iodoethyl, 2-iodoethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2-tris Chloroethyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 3,3-difluoropropyl, 3 ,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-fluoropropane-2-yl, 2-fluoropropane-2-yl, 1, 1-difluoropropane-2-yl, 1,2-difluoropropane-2-yl, 1,3-difluoropropane-2-yl, 1,2,3-trifluoropropane-2-yl, 1, 1,3,3-tetrafluoropropane-2-yl, 1,1,1,3,3,3-hexafluoropropane-2-yl, heptafluoropropane-2-yl, 1-chloropropyl, 2-chloropropyl Group, 3-chloropropyl, 1,1-dichloropropyl, 2,2-dichloropropyl, 3,3-dichloropropyl, 3,3,3-trichloropropyl, 2,2, 3,3,3-pentachloropropyl, heptachloropropyl, 1-chloropropane-2-yl, 2-chloropropane-2-yl, 1,1-dichloropropane-2-yl, 1,2- Dichloropropane-2-yl, 1,3-dichloropropane-2-yl, 1,2,3-trichloropropane-2-yl, 1,1,3,3-tetrachloropropane-2-yl, 1,1,1,3,3,3-hexachloropropane-2-yl, heptachloropropane-2-yl, 1-bromopropyl, 2-bromopropyl, 3-bromopropyl, 1-bromopropane -2-yl, 2-bromopropane-2-yl, 1-iodopropyl, 2-iodopropyl, 3-iodopropyl, 1-iodopropane-2-yl, 2-iodopropane-2-yl, 1-fluorobutyl, 2-fluorobutyl, 3-fluorobutyl, 4-fluorobutyl, 4,4-difluorobutyl, 4,4,4-trifluorobutyl, 3,3,4, 4,4-pentafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl, nonafluorobutyl, 1,1,1-trifluorobutan-2-yl, 4, 4,4-trifluorobutane-2-yl, 3,3,4,4,4-pentafluorobutane-2-yl, nonafluorobutane-2-yl, 1,1,1,3,3 ,3-Hexafluoro-2-(trifluoromethyl)propane-2-yl, 1-chlorobutyl, 2-chlorobutyl, 3-chlorobutyl, 4-chlorobutyl, 4,4-dichloro Butyl, 4,4,4-trichloro Butyl, nonachlorobutyl, 1,1,1-trichlorobutan-2-yl, 4,4,4-trichlorobutan-2-yl, nonachlorobutan-2-yl, 1-bromo Butyl, 2-bromobutyl, 3-bromobutyl, 4-bromobutyl, 1-iodobutyl, 2-iodobutyl, 3-iodobutyl, 4-iodobutyl, 4-chloro-1 ,1,2,2,3,3,4,4-octafluorobutyl, 4-bromo-1,1,2,2,3,3,4,4-octafluorobutyl, 1-fluoropentyl , 2-fluoropentyl, 3-fluoropentyl, 4-fluoropentyl, 5-fluoropentyl, 5,5,5-trifluoropentyl, 4,4,5,5,5-pentafluoropentyl , 3,3,4,4,5,5,5-heptafluoropentyl, 2,2,3,3,4,4,5,5,5-nonafluoropentyl, undecafluoropentyl, 1 -Chloropentyl, 2-chloropentyl, 3-chloropentyl, 4-chloropentyl, 5-chloropentyl, 5,5,5-trichloropentyl, 4,4,5,5,5- Pentachloropentyl, 3,3,4,4,5,5,5-heptachloropentyl, 2,2,3,3,4,4,5,5,5-nonachloropentyl, undecyl chloride Amyl, 1-bromopentyl, 2-bromopentyl, 3-bromopentyl, 4-bromopentyl, 5-bromopentyl, 5-iodopentyl, 1-fluorohexyl, 2-fluorohexyl, 3 -Fluorohexyl, 4-fluorohexyl, 5-fluorohexyl, 6-fluorohexyl, 6,6,6-trifluorohexyl, 5,5,6,6,6-pentafluorohexyl, 4,4,5,5 ,6,6,6-heptafluorohexyl, 3,3,4,4,5,5,6,6,6-nonafluorohexyl, 2,2,3,3,4,4,5,5,6 , 6,6-undecylfluorohexyl, tridecylfluorohexyl, 1-chlorohexyl, 2-chlorohexyl, 3-chlorohexyl, 4-chlorohexyl, 5-chlorohexyl, 6-chlorohexyl, 5-bromohexyl, Groups such as 6-bromohexyl, 5-iodohexyl or 6-iodohexyl.

於本發明中所謂「C3至C6環烷基」在無特別限定下係表示碳數為3至6的環烷基，可列舉例如：環丙基、環丁基、環戊基或環己基等基。 In the present invention, “C 3 to C 6 cycloalkyl” means a cycloalkyl group having 3 to 6 carbon atoms without particular limitation, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, or cyclo Hexyl and other groups.

於本發明中所謂「C3至C6鹵環烷基」在無特別限定下係表示經相同或相異之1至11個鹵素原子取代之碳數為3至6的環烷基，可列舉例如：1-氟環丙基、2-氟環丙基、2,2-二氟環丙基、2,2,3,3-四氟環丙基、1-氯環丙基、2-氯環丙基、2,2-二氯環丙基、2,2,3,3-四氯環丙基、2,2-二溴環丙基、2,2-二碘環丙基、1-氟環丁基、2-氟環丁基、3-氟環丁基、3,3-二氟環丁基、七氟環丁基、2-氯環丁基、3-氯環丁基、3,3-二氯環丁基、3,3-二溴環丁基、3,3-二碘環丁基、1-氟環戊基、2-氟環戊基、3-氟環戊基、2,2-二氟環戊基、3,3-二氟環戊基、九氟環戊基、2,2-二氯環戊基、3,3-二氯環戊基、2,2-二溴環戊基、3,3-二溴環戊基、2,2-二碘環戊基、3,3-二碘環戊基、1-氟環己基、2-氟環己基、3-氟環己基、4-氟環己基、2,2-二氟環己基、 3,3-二氟環己基、4,4-二氟環己基、1-氯環己基、2-氯環己基、3-氯環己基、4-氯環己基、2,2-二氯環己基、3,3-二氯環己基、4,4-二氯環己基、3,3-二溴環己基、4,4-二溴環己基、3,3-二碘環己基或4,4-二碘環己基等基。 In the present invention, the so-called "C 3 to C 6 halocycloalkyl" means a cycloalkyl group having 3 to 6 carbon atoms substituted with the same or different 1 to 11 halogen atoms, without particular limitation. For example: 1-fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl, 1-chlorocyclopropyl, 2-chloro Cyclopropyl, 2,2-dichlorocyclopropyl, 2,2,3,3-tetrachlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-diiodocyclopropyl, 1- Fluorocyclobutyl, 2-fluorocyclobutyl, 3-fluorocyclobutyl, 3,3-difluorocyclobutyl, heptafluorocyclobutyl, 2-chlorocyclobutyl, 3-chlorocyclobutyl, 3 ,3-dichlorocyclobutyl, 3,3-dibromocyclobutyl, 3,3-diiodocyclobutyl, 1-fluorocyclopentyl, 2-fluorocyclopentyl, 3-fluorocyclopentyl, 2,2-difluorocyclopentyl, 3,3-difluorocyclopentyl, nonafluorocyclopentyl, 2,2-dichlorocyclopentyl, 3,3-dichlorocyclopentyl, 2,2- Dibromocyclopentyl, 3,3-dibromocyclopentyl, 2,2-diiodocyclopentyl, 3,3-diiodocyclopentyl, 1-fluorocyclohexyl, 2-fluorocyclohexyl, 3- Fluorocyclohexyl, 4-fluorocyclohexyl, 2,2-difluorocyclohexyl, 3,3-difluorocyclohexyl, 4,4-difluorocyclohexyl, 1-chlorocyclohexyl, 2-chlorocyclohexyl, 3 -Chlorocyclohexyl, 4-chlorocyclohexyl, 2,2-dichlorocyclohexyl, 3,3-dichlorocyclohexyl, 4,4-dichlorocyclohexyl, 3,3-dibromocyclohexyl, 4,4 -Dibromocyclohexyl, 3,3-diiodocyclohexyl or 4,4-diiodocyclohexyl and other groups.

於本發明中所謂「C2至C6烯基」在無特別限定下係表示碳數為2至6之直鏈或分枝鏈狀的烯基，可列舉例如：乙烯基、1-丙烯基、異丙烯基、2-丙烯基、1-丁烯基、1-甲基-1-丙烯基、2-丁烯基、1-甲基-2-丙烯基、3-丁烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、1,3-丁二烯基、1-戊烯基、1-乙基-2-丙烯基、2-戊烯基、1-甲基-1-丁烯基、3-戊烯基、1-甲基-2-丁烯基、4-戊烯基、1-甲基-3-丁烯基、3-甲基-1-丁烯基、1,2-二甲基-2-丙烯基、1,1-二甲基-2-丙烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1,2-二甲基-1-丙烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,3-戊二烯基、1-乙烯基-2-丙烯基、1-己烯基、1-丙基-2-丙烯基、2-己烯基、1-甲基-1-戊烯基、1-乙基-2-丁烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-4-戊烯基、1-乙基-3-丁烯基、1-(異丁基)乙烯基、1-乙基-1-甲基-2-丙烯基、1-乙基-2-甲基-2-丙烯基、1-(異丙基)-2-丙烯基、2-甲基-2-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1,3-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1,5-己二烯基、1-乙烯基-3-丁烯基或2,4-己二烯基等基。 In the present invention, the "C 2 to C 6 alkenyl group" refers to a straight-chain or branched-chain alkenyl group having 2 to 6 carbon atoms without particular limitation, and examples thereof include vinyl groups and 1-propenyl groups. , Isopropenyl, 2-propenyl, 1-butenyl, 1-methyl-1-propenyl, 2-butenyl, 1-methyl-2-propenyl, 3-butenyl, 2- Methyl-1-propenyl, 2-methyl-2-propenyl, 1,3-butadienyl, 1-pentenyl, 1-ethyl-2-propenyl, 2-pentenyl, 1 -Methyl-1-butenyl, 3-pentenyl, 1-methyl-2-butenyl, 4-pentenyl, 1-methyl-3-butenyl, 3-methyl-1 -Butenyl, 1,2-dimethyl-2-propenyl, 1,1-dimethyl-2-propenyl, 2-methyl-2-butenyl, 3-methyl-2-butene Alkenyl, 1,2-dimethyl-1-propenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,3-pentadienyl, 1-ethylene 2-propenyl, 1-hexenyl, 1-propyl-2-propenyl, 2-hexenyl, 1-methyl-1-pentenyl, 1-ethyl-2-butenyl , 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-4-pentenyl, 1-ethyl-3-butenyl, 1-(isobutyl) vinyl , 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-2-propenyl, 1-(isopropyl)-2-propenyl, 2-methyl-2 -Pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1,3-dimethyl-2-butenyl, 1,1-dimethyl-3 -Butenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-3 -Butenyl, 1,1,2-trimethyl-2-propenyl, 1,5-hexadienyl, 1-vinyl-3-butenyl or 2,4-hexadienyl .

於本發明中所謂「C2至C6鹵烯基」在無特別限定下係表示經相同或相異之1至11個鹵素原子取代之碳數為2至6之直鏈或分枝鏈狀的烯基，可列舉例如：1-氟乙烯基、2-氟乙烯基、1,2-二氟乙烯基、2,2- 二氟乙烯基、三氟乙烯基、1-氯乙烯基、2-氯乙烯基、1,2-二氯乙烯基、2,2-二氯乙烯基、三氯乙烯基、1,2-二溴乙烯基、2,2-二溴乙烯基、三溴乙烯基、1,2-二碘乙烯基、2,2-二碘乙烯基、三碘乙烯基、1-氟-2-丙烯基、2-氟-2-丙烯基、3-氟-2-丙烯基、2,3-二氟-2-丙烯基、3,3-二氟-2-丙烯基、3,3-二氟-1-丙烯基、2,3,3-三氟-2-丙烯基、3,3,3-三氟-1-丙烯基、2-氯-3,3,3-三氟-1-丙烯基、1,2,3,3,3-五氟-1-丙烯基、1-氯-2-丙烯基、2-氯-2-丙烯基、3-氯-2-丙烯基、2,3-二氯-2-丙烯基、3,3-二氯-2-丙烯基、3,3-二氯-1-丙烯基、2,3,3-三氯-2-丙烯基、3,3,3-三氯-1-丙烯基、3-溴-2-丙烯基、3,3-二溴-2-丙烯基、3,3-二碘-2-丙烯基、2,2-二氟-1-丙烯-2-基、3,3,3-三氟-1-丙烯-2-基、3,3,3-三氯-1-丙烯-2-基、4-氟-3-丁烯基、4,4-二氟-3-丁烯基、4,4-二氟-3-丁烯-2-基、4,4,4-三氟-2-丁烯基、3,4,4-三氟-3-丁烯基、2-三氟甲基-2-丙烯基、2-三氟甲基-3,3-二氟-2-丙烯基、4,4,4-三氟-3-氯-2-丁烯基、4,4-二氯-3-丁烯基、4,4,4-三氯-2-丁烯基、2-三氯甲基-2-丙烯基、5,5-二氟-4-戊烯基、4,5,5-三氟-4-戊烯基、5,5,5-三氟-3-戊烯基、4,4,4-三氟-3-甲基-2-丁烯基、4,4,4-三氟-3-三氟甲基-2-丁烯基、5,5-二氯-4-戊烯基、4,4,4-三氯-3-甲基-2-丁烯基、6,6-二氟-5-己烯基、5,6,6-三氟-5-戊烯基、6,6,6-三氟-4-戊烯基、5,5,5-三氟-4-甲基-3-戊烯基、5,5,5-三氟-4-三氟甲基-3-戊烯基、6,6-二氯-5-己烯基或5,5,5-三氯-4-甲基-3-戊烯基等基。 In the present invention, the term "C 2 to C 6 haloalkenyl" means, without particular limitation, a linear or branched chain of 2 to 6 carbon atoms substituted with the same or different 1 to 11 halogen atoms The alkenyl group includes, for example, 1-fluorovinyl, 2-fluorovinyl, 1,2-difluorovinyl, 2,2-difluorovinyl, trifluorovinyl, 1-chlorovinyl, 2 -Chlorovinyl, 1,2-dichlorovinyl, 2,2-dichlorovinyl, trichlorovinyl, 1,2-dibromovinyl, 2,2-dibromovinyl, tribromovinyl , 1,2-diiodovinyl, 2,2-diiodovinyl, triiodovinyl, 1-fluoro-2-propenyl, 2-fluoro-2-propenyl, 3-fluoro-2-propenyl , 2,3-difluoro-2-propenyl, 3,3-difluoro-2-propenyl, 3,3-difluoro-1-propenyl, 2,3,3-trifluoro-2-propenyl , 3,3,3-trifluoro-1-propenyl, 2-chloro-3,3,3-trifluoro-1-propenyl, 1,2,3,3,3-pentafluoro-1-propenyl , 1-chloro-2-propenyl, 2-chloro-2-propenyl, 3-chloro-2-propenyl, 2,3-dichloro-2-propenyl, 3,3-dichloro-2-propenyl Group, 3,3-dichloro-1-propenyl, 2,3,3-trichloro-2-propenyl, 3,3,3-trichloro-1-propenyl, 3-bromo-2-propenyl , 3,3-dibromo-2-propenyl, 3,3-diiodo-2-propenyl, 2,2-difluoro-1-propen-2-yl, 3,3,3-trifluoro-1 -Propen-2-yl, 3,3,3-trichloro-1-propen-2-yl, 4-fluoro-3-butenyl, 4,4-difluoro-3-butenyl, 4,4 -Difluoro-3-buten-2-yl, 4,4,4-trifluoro-2-butenyl, 3,4,4-trifluoro-3-butenyl, 2-trifluoromethyl- 2-propenyl, 2-trifluoromethyl-3,3-difluoro-2-propenyl, 4,4,4-trifluoro-3-chloro-2-butenyl, 4,4-dichloro- 3-butenyl, 4,4,4-trichloro-2-butenyl, 2-trichloromethyl-2-propenyl, 5,5-difluoro-4-pentenyl, 4,5, 5-trifluoro-4-pentenyl, 5,5,5-trifluoro-3-pentenyl, 4,4,4-trifluoro-3-methyl-2-butenyl, 4,4, 4-trifluoro-3-trifluoromethyl-2-butenyl, 5,5-dichloro-4-pentenyl, 4,4,4-trichloro-3-methyl-2-butenyl , 6,6-difluoro-5-hexenyl, 5,6,6-trifluoro-5-pentenyl, 6,6,6-trifluoro-4-pentenyl, 5,5,5- Trifluoro-4-methyl-3-pentenyl, 5,5,5-trifluoro-4-trifluoromethyl-3-pentenyl, 6,6-dichloro-5-hexenyl or 5 , 5,5-trichloro-4-methyl-3-pentenyl and other groups.

於本發明中所謂「C2至C6炔基」在無特別限定下係表示碳數為2至6之直鏈或分枝鏈狀的炔基，可列舉例如：乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、1-甲基-2-丙炔基、2-丁炔基、3-丁炔基、1-戊炔基、1-乙基-2-丙炔基、2-戊炔基、3-戊炔基、1-甲基-2-丁炔基、4-戊炔基、1- 甲基-3-丁炔基、2-甲基-3-丁炔基、1-己炔基、1-(正丙基)-2-丙炔基、2-己炔基、1-乙基-2-丁炔基、3-己炔基、1-甲基-2-戊炔基、1-甲基-3-戊炔基、4-甲基-1-戊炔基、3-甲基-1-戊炔基、5-己炔基、1-乙基-3-丁炔基、1-乙基-1-甲基-2-丙炔基、1-(異丙基)-2-丙炔基、1,1-二甲基-2-丁炔基或2,2-二甲基-3-丁炔基等基。 In the present invention, the "C 2 to C 6 alkynyl group" refers to a straight or branched chain alkynyl group having 2 to 6 carbon atoms without particular limitation, and examples thereof include ethynyl and 1-propyne Group, 2-propynyl, 1-butynyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 1-ethyl-2- Propynyl, 2-pentynyl, 3-pentynyl, 1-methyl-2-butynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3 -Butynyl, 1-hexynyl, 1-(n-propyl)-2-propynyl, 2-hexynyl, 1-ethyl-2-butynyl, 3-hexynyl, 1- Methyl-2-pentynyl, 1-methyl-3-pentynyl, 4-methyl-1-pentynyl, 3-methyl-1-pentynyl, 5-hexynyl, 1- Ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, 1-(isopropyl)-2-propynyl, 1,1-dimethyl-2-butane Alkynyl or 2,2-dimethyl-3-butynyl and other groups.

於本發明中所謂「C2至C6鹵炔基」在無特別限定下係表示經相同或相異之1至9個鹵素原子取代之碳數為2至6之直鏈或分枝鏈狀的炔基，可列舉例如：氟乙炔基、氯乙炔基、溴乙炔基、碘乙炔基、3-氟-2-丙炔基、3-氯-2-丙炔基、3-溴-2-丙炔基、3-碘-2-丙炔基、4-氟-3-丁炔基、4-氯-3-丁炔基、4-溴-3-丁炔基、4-碘-3-丁炔基、4,4-二氟-2-丁炔基、4,4-二氯-2-丁炔基、4,4,4-三氟-2-丁炔基、4,4,4-三氯-2-丁炔基、3-氟-1-甲基-2-丙炔基、3-氯-1-甲基-2-丙炔基、5-氟-4-戊炔基、5-氯-4-戊炔基、5,5,5-三氟-3-戊炔基、5,5,5-三氯-3-戊炔基、4-氟-2-甲基-3-丁炔基、4-氯-2-甲基-3-丁炔基、6-氟-5-己炔基、6-氯-5-己炔基、6,6,6-三氟-4-己炔基、6,6,6-三氯-4-己炔基、5-氟-3-甲基-4-戊炔基或5-氯-3-甲基-4-戊炔基等基。 In the present invention, the term "C 2 to C 6 haloalkynyl" refers to a straight or branched chain of 2 to 6 carbon atoms substituted with the same or different 1 to 9 halogen atoms, unless otherwise specified. The alkynyl group includes, for example, fluoroethynyl, chloroethynyl, bromoethynyl, iodoethynyl, 3-fluoro-2-propynyl, 3-chloro-2-propynyl, 3-bromo-2- Propynyl, 3-iodo-2-propynyl, 4-fluoro-3-butynyl, 4-chloro-3-butynyl, 4-bromo-3-butynyl, 4-iodo-3- Butynyl, 4,4-difluoro-2-butynyl, 4,4-dichloro-2-butynyl, 4,4,4-trifluoro-2-butynyl, 4,4,4 -Trichloro-2-butynyl, 3-fluoro-1-methyl-2-propynyl, 3-chloro-1-methyl-2-propynyl, 5-fluoro-4-pentynyl, 5-chloro-4-pentynyl, 5,5,5-trifluoro-3-pentynyl, 5,5,5-trichloro-3-pentynyl, 4-fluoro-2-methyl-3 -Butynyl, 4-chloro-2-methyl-3-butynyl, 6-fluoro-5-hexynyl, 6-chloro-5-hexynyl, 6,6,6-trifluoro-4 -Hexynyl, 6,6,6-trichloro-4-hexynyl, 5-fluoro-3-methyl-4-pentynyl or 5-chloro-3-methyl-4-pentynyl, etc. base.

於本發明中所謂「C1至C6烷氧基」在無特別限定下係表示烷基部分為上述意義之(C1至C6烷基)-O-基，可列舉例如：甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、第二丁氧基、第三丁氧基、正戊氧基、1-甲基丁氧基、2-甲基丁氧基、3-甲基丁氧基、1-乙基丙氧基、1,1-二甲基丙氧基、1,2-二甲基丙氧基或正己氧基等基。 In the present invention, the term "C 1 to C 6 alkoxy" refers to an (C 1 to C 6 alkyl)-O- group having the above-mentioned meaning unless otherwise specified. Examples include: methoxy , Ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, second butoxy, third butoxy, n-pentyloxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1-ethylpropoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy or n-hexyloxy, etc. base.

於本發明中所謂「C1至C6鹵烷氧基」，在無特別限定下係表示鹵烷基部分為上述意義之(C1至C6鹵烷基)-O-基，可列舉例如：二氟 甲氧基、二氯甲氧基、三氟甲氧基、三氯甲氧基、三溴甲氧基、氯二氟甲氧基、溴二氟甲氧基、2-氟乙氧基、1-氯乙氧基、2-氯乙氧基、1-溴乙氧基、2-溴乙氧基、2,2-二氟乙氧基、1,2-二氯乙氧基、2,2-二氯乙氧基、2,2,2-三氟乙氧基、2,2,2-三氯乙氧基、1,1,2,2-四氟乙氧基、五氟乙氧基、2-溴-2-氯乙氧基、2-氯-1,1,2,2-四氟乙氧基、1-氯-1,2,2,2-四氟乙氧基、1-氯丙氧基、2-氯丙氧基、3-氯丙氧基、2-溴丙氧基、3-溴丙氧基、2-溴-1-甲基乙氧基、3-碘丙氧基、2,3-二氯丙氧基、2,3-二溴丙氧基、3,3,3-三氟丙氧基、3,3,3-三氟-2-丙氧基、3,3,3-三氯丙氧基、3-溴-3,3-二氟丙氧基、2,2-二氟丙氧基、3,3-二氯-3-氟丙氧基、2,2,3,3-四氟丙氧基、1-溴-3,3,3-三氟丙氧基、2,2,3,3,3-五氟丙氧基、2,2,2-三氟-1-三氟甲基乙氧基、七氟丙氧基、七氟-2-丙氧基、1,2,2,2-四氟-1-三氟甲基乙氧基、1,1,2,3,3,3-六氟丙氧基、2-氯丁氧基、3-氯丁氧基、4-氯丁氧基、2-氯-1,1-二甲基乙氧基、4-溴丁氧基、3-溴-2-甲基丙氧基、2-溴-1,1-二甲基乙氧基、2,2-二氯-1,1-二甲基乙氧基、2-氯-1-氯甲基-2-甲基乙氧基、4,4,4-三氟丁氧基、3,3,3-三氟-1-甲基丙氧基、3,3,3-三氟-2-甲基丙氧基、2,3,4-三氯丁氧基、2,2,2-三氯-1,1-二甲基乙氧基、4-氯-4,4-二氟丁氧基、4,4-二氯-4-氟丁氧基、4-溴-4,4-二氟丁氧基、2,4-二溴-4,4-二氟丁氧基、3,4-二氯-3,4,4-三氟丁氧基、3,3-二氯-4,4,4-三氟丁氧基、4-溴-3,3,4,4-四氟丁氧基、4-溴-3-氯-3,4,4-三氟丁氧基、2,2,3,3,4,4-六氟丁氧基、2,2,3,4,4,4-六氟丁氧基、2,2,2-三氟-1-甲基-1-三氟甲基乙氧基、3,3,3-三氟-2-三氟甲基丙氧基、2,2,3,3,4,4,4-七氟丁氧基、3,3,4,4,4-五氟-2-丁氧基、2,3,3,3-四氟-2-三氟甲基丙氧基、1,1,2,2,3,3,4,4-八氟丁氧基、九氟丁氧基、全氟第三丁氧基、4-氯- 1,1,2,2,3,3,4,4-八氟丁氧基、5,5,5-三氟戊氧基、4,4,5,5,5-五氟戊氧基、3,3,4,4,5,5,5-七氟戊氧基、3,3,4,4,5,5,5-七氟-2-戊氧基、2,2,3,3,4,4,5,5,5-九氟戊氧基、2,2,3,3,4,4,5,5-八氟戊氧基、全氟戊氧基、4,4,5,5,5-五氟-2-丁氧基、2,2-雙(三氟甲基)丙氧基、2,2,3,3,4,4,5,5,6,6,6-十一氟己氧基、3,3,4,4,5,5,6,6,6-九氟己氧基、4,4,5,5,6,6,6-七氟己氧基、2,2,3,3,4,4,5,5,6,6-十氟己氧基、4,4,4-三氟-3,3-雙(三氟甲基)丁基氧基、全氟己氧基等基。 In the present invention, the so-called "C 1 to C 6 haloalkoxy group" means, without particular limitation, that the haloalkyl part is the (C 1 to C 6 haloalkyl)-O- group in the above meaning, and examples include : Difluoromethoxy, dichloromethoxy, trifluoromethoxy, trichloromethoxy, tribromomethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy Group, 1-chloroethoxy, 2-chloroethoxy, 1-bromoethoxy, 2-bromoethoxy, 2,2-difluoroethoxy, 1,2-dichloroethoxy, 2,2-dichloroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, 1,1,2,2-tetrafluoroethoxy, pentafluoro Ethoxy, 2-bromo-2-chloroethoxy, 2-chloro-1,1,2,2-tetrafluoroethoxy, 1-chloro-1,2,2,2-tetrafluoroethoxy , 1-chloropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2-bromo-1-methylethoxy, 3- Iodopropoxy, 2,3-dichloropropoxy, 2,3-dibromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trifluoro-2-propoxy Group, 3,3,3-trichloropropoxy, 3-bromo-3,3-difluoropropoxy, 2,2-difluoropropoxy, 3,3-dichloro-3-fluoropropoxy Group, 2,2,3,3-tetrafluoropropoxy, 1-bromo-3,3,3-trifluoropropoxy, 2,2,3,3,3-pentafluoropropoxy, 2, 2,2-trifluoro-1-trifluoromethylethoxy, heptafluoropropoxy, heptafluoro-2-propoxy, 1,2,2,2-tetrafluoro-1-trifluoromethyl ethyl Oxy, 1,1,2,3,3,3-hexafluoropropoxy, 2-chlorobutoxy, 3-chlorobutoxy, 4-chlorobutoxy, 2-chloro-1,1- Dimethylethoxy, 4-bromobutoxy, 3-bromo-2-methylpropoxy, 2-bromo-1,1-dimethylethoxy, 2,2-dichloro-1, 1-dimethylethoxy, 2-chloro-1-chloromethyl-2-methylethoxy, 4,4,4-trifluorobutoxy, 3,3,3-trifluoro-1- Methylpropoxy, 3,3,3-trifluoro-2-methylpropoxy, 2,3,4-trichlorobutoxy, 2,2,2-trichloro-1,1-dimethyl Ethoxy, 4-chloro-4,4-difluorobutoxy, 4,4-dichloro-4-fluorobutoxy, 4-bromo-4,4-difluorobutoxy, 2,4 -Dibromo-4,4-difluorobutoxy, 3,4-dichloro-3,4,4-trifluorobutoxy, 3,3-dichloro-4,4,4-trifluorobutoxy Group, 4-bromo-3,3,4,4-tetrafluorobutoxy, 4-bromo-3-chloro-3,4,4-trifluorobutoxy, 2,2,3,3,4, 4-hexafluorobutoxy, 2,2,3,4,4,4-hexafluorobutoxy, 2,2,2-trifluoro-1-methyl-1-trifluoromethylethoxy, 3,3,3-trifluoro-2-trifluoromethylpropoxy, 2,2,3,3,4,4,4-heptafluorobutoxy, 3,3,4,4,4-penta Fluoro-2-butoxy, 2,3,3,3-tetrafluoro-2-trifluoromethylpropoxy, 1,1,2,2 ,3,3,4,4-octafluorobutoxy, nonafluorobutoxy, perfluoro third butoxy, 4-chloro- 1,1,2,2,3,3,4,4-octa Fluorobutoxy, 5,5,5-trifluoropentyloxy, 4,4,5,5,5-pentafluoropentyloxy, 3,3,4,4,5,5,5-heptafluoropentyl Oxygen, 3,3,4,4,5,5,5-heptafluoro-2-pentyloxy, 2,2,3,3,4,4,5,5,5-nonafluoropentyloxy, 2,2,3,3,4,4,5,5-octafluoropentyloxy, perfluoropentyloxy, 4,4,5,5,5-pentafluoro-2-butoxy, 2,2 -Bis(trifluoromethyl)propoxy, 2,2,3,3,4,4,5,5,6,6,6-undecylfluorohexyloxy, 3,3,4,4,5 ,5,6,6,6-nonafluorohexyloxy, 4,4,5,5,6,6,6-heptafluorohexyloxy, 2,2,3,3,4,4,5,5 , 6,6-decafluorohexyloxy, 4,4,4-trifluoro-3,3-bis (trifluoromethyl) butyloxy, perfluorohexyloxy and other groups.

於本發明中所謂「C2至C6烯基氧基」在無特別限定下係表示烯基部分為上述意義之(C2至C6烯基)-O-基，可列舉例如：2-丙烯基氧基、1-甲基-2-丙烯基氧基、2-甲基-2-丙烯基氧基、2-丁烯基氧基、3-丁烯基氧基、3-甲基-2-丁烯基氧基、4-甲基-3-丁烯基氧基、4-戊烯基氧基或5-己烯基氧基等基。 In the present invention, the so-called "C 2 to C 6 alkenyloxy group" means that the alkenyl moiety is (C 2 to C 6 alkenyl)-O- group in the above meaning without particular limitation, and examples include: 2- Propenyloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-butenyloxy, 3-butenyloxy, 3-methyl- Groups such as 2-butenyloxy, 4-methyl-3-butenyloxy, 4-pentenyloxy or 5-hexenyloxy.

於本發明中所謂「C2至C6鹵烯基氧基」在無特別限定下係表示鹵烯基部分為上述意義之(C2至C6鹵烯基)-O-基，可列舉例如：3-氯-2-丙烯基氧基、3,3-二氯-2-丙烯基氧基、3,3-二氟-2-丙烯基氧基、3,3,3-三氟-1-丙烯基氧基、2,3,3,3-四氟-1-丙烯基氧基、4,4,4-三氟-2-丁烯基氧基、3,4,4-三氟-3-丁烯基氧基、5-氯-3-戊烯基氧基或6-氟-2-己烯基氧基等基。 In the present invention, the so-called "C 2 to C 6 haloalkenyloxy group" means that the haloalkenyl moiety is (C 2 to C 6 haloalkenyl)-O- group without any particular limitation, and examples include : 3-chloro-2-propenyloxy, 3,3-dichloro-2-propenyloxy, 3,3-difluoro-2-propenyloxy, 3,3,3-trifluoro-1 -Propenyloxy, 2,3,3,3-tetrafluoro-1-propenyloxy, 4,4,4-trifluoro-2-butenyloxy, 3,4,4-trifluoro- Groups such as 3-butenyloxy, 5-chloro-3-pentenyloxy or 6-fluoro-2-hexenyloxy.

於本發明中所謂「C2至C6炔基氧基」在無特別限定下係表示炔基部分為上述意義之(C2至C6炔基)-O-基，可列舉例如：2-丙炔基氧基、1-甲基-2-丙炔基氧基、1-乙基-2-丙炔基氧基、2-丁炔基氧基、3-丁炔基氧基、1-甲基-2-丁炔基氧基、2-戊炔基氧基、4-戊炔基氧基或4,4-二甲基-2-戊炔基氧基等基。 In the present invention, the so-called "C 2 to C 6 alkynyloxy group" means that the alkynyl moiety is (C 2 to C 6 alkynyl)-O- group in the above meaning without particular limitation, and examples include: 2- Propynyloxy, 1-methyl-2-propynyloxy, 1-ethyl-2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1- Groups such as methyl-2-butynyloxy, 2-pentynyloxy, 4-pentynyloxy or 4,4-dimethyl-2-pentynyloxy.

於本發明中所謂「C2至C6鹵炔基氧基」，在無特別限定下係表示鹵炔基部分為上述意義之(C2至C6鹵炔基)-O-基，可列舉例如：4,4,4-三氟-2-丁炔基氧基、5,5,5-三氟-3-戊炔基氧基或1-甲基-4,4,4-三氟-2-丁炔基氧基等基。 In the present invention, the so-called "C 2 to C 6 haloalkynyloxy group" means that the haloalkynyl part is (C 2 to C 6 haloalkynyl)-O- group without the above-mentioned meaning, and can be exemplified For example: 4,4,4-trifluoro-2-butynyloxy, 5,5,5-trifluoro-3-pentynyloxy or 1-methyl-4,4,4-trifluoro- 2-butynyloxy and other groups.

於本發明中所謂「C3至C6環烷基氧基」在無特別限定下係表示環烷基部分為上述意義之(C3至C6環烷基)-O-基，可列舉例如：環丙氧基、環丁氧基、環戊基氧基或環己氧基等基。 In the present invention, the so-called "C 3 to C 6 cycloalkyloxy" means that the cycloalkyl moiety is the (C 3 to C 6 cycloalkyl)-O- group in the above meaning without particular limitation, and examples include : Cyclopropoxy, cyclobutoxy, cyclopentyloxy or cyclohexyloxy and other groups.

於本發明中所謂「C3至C6鹵環烷基氧基」在無特別限定下係表示鹵環烷基部分為上述意義之(C3至C6鹵環烷基)-O-基，可列舉例如：2,2-二氟環丙氧基、2,2-二氯環丙氧基、3,3-二氟環丁氧基、3,3-二氯環丁氧基、3-氟環戊基氧基、3,3-二氟環戊基氧基、九氟環戊基氧基、3,3-二氯環戊基氧基、4,4-二氟環己氧基或4,4-二氯環己氧基等基。 In the present invention, the so-called "C 3 to C 6 halocycloalkyloxy" means that the halocycloalkyl moiety is the above-mentioned (C 3 to C 6 halocycloalkyl)-O- group, without particular limitation, For example, 2,2-difluorocyclopropoxy, 2,2-dichlorocyclopropoxy, 3,3-difluorocyclobutoxy, 3,3-dichlorocyclobutoxy, 3- Fluorocyclopentyloxy, 3,3-difluorocyclopentyloxy, nonafluorocyclopentyloxy, 3,3-dichlorocyclopentyloxy, 4,4-difluorocyclohexyloxy or 4,4-Dichlorocyclohexyloxy and other groups.

於本發明中所謂「芳香族雜環氧基」在無特別限定下係表示芳香族雜環部分為上述意義之(芳香族雜環)-O-基，可列舉例如：吡啶-2-基氧基、吡啶-3-基氧基、吡啶-4-基氧基、吡

Figure 108129126-A0202-12-0034-126
-2-基氧基、嗒
Figure 108129126-A0202-12-0034-127
-3-基氧基、嗒
Figure 108129126-A0202-12-0034-128
-4-基氧基、嘧啶-2-基氧基、嘧啶-4-基氧基、嘧啶-5-基氧基、噻唑-2-基氧基、噻唑-4-基氧基或噻唑-5-基氧基等基。 In the present invention, the term "aromatic heterocyclic oxy group" means that the aromatic heterocyclic moiety is (aromatic heterocyclic)-O- group of the above meaning without particular limitation, and examples include pyridin-2-yloxy Group, pyridin-3-yloxy, pyridin-4-yloxy, pyridine
Figure 108129126-A0202-12-0034-126
-2-yloxy, ta
Figure 108129126-A0202-12-0034-127
-3-yloxy, ta
Figure 108129126-A0202-12-0034-128
-4-yloxy, pyrimidin-2-yloxy, pyrimidin-4-yloxy, pyrimidin-5-yloxy, thiazol-2-yloxy, thiazol-4-yloxy or thiazole-5 -Radicals such as radicals.

於本發明中所謂「飽和雜環氧基」在無特別限定下係表示飽和雜環部分為上述意義之(飽和雜環)-O-基，可列舉例如：氧環丁烷-3-基氧基、四氫呋喃-2-基氧基、四氫呋喃-3-基氧基、(四氫-2H-啶喃-2-基)氧基、(四氫-2H-哌喃-3-基)氧基或(四氫-2H-哌喃-4-基)氧基等基。 In the present invention, the term "saturated heterocyclic oxy group" means that the saturated heterocyclic moiety is a (saturated heterocyclic)-O- group of the above meaning without particular limitation, and examples include oxycyclobutane-3-yloxy Group, tetrahydrofuran-2-yloxy, tetrahydrofuran-3-yloxy, (tetrahydro-2H-pyran-2-yl)oxy, (tetrahydro-2H-piperan-3-yl)oxy or (Tetrahydro-2H-piperan-4-yl)oxy and other groups.

於本發明中所謂「C1至C6烷基硫基」在無特別限定下係表示烷基部分為上述意義之(C1至C6烷基)-S-基，可列舉例如：甲基硫基、乙基硫基、正丙基硫基、異丙基硫基、正丁基硫基、異丁基硫基、第二丁基硫基或第三丁基硫基、戊基硫基、己基硫基等基。 In the present invention, the so-called "C 1 to C 6 alkylthio group" means that the alkyl portion is the (C 1 to C 6 alkyl)-S- group in the above meaning without particular limitation, and examples include: methyl Sulfur, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, second or third butylthio, pentylthio , Hexylthio and other groups.

於本發明中所謂「C1至C6烷基亞磺醯基」在無特別限定下係表示烷基部分為上述意義之(C1至C6烷基)-S(=O)-基，可列舉例如：甲基亞磺醯基、乙基亞磺醯基、正丙基亞磺醯基、異丙基亞磺醯基、正丁基亞磺醯基、異丁基亞磺醯基、第二丁基亞磺醯基、第三丁基亞磺醯基、戊基亞磺醯基或己基亞磺醯基等基。 In the present invention, the so-called "C 1 to C 6 alkylsulfinyl group" means that the alkyl portion is the (C 1 to C 6 alkyl)-S(=O)- group in the above meaning unless otherwise specified. For example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, Groups such as second butylsulfinyl, third butylsulfinyl, pentylsulfinyl, or hexylsulfinyl.

於本發明中所謂「C1至C6烷基磺醯基」，在無特別限定下係表示烷基部分為上述意義之(C1至C6烷基)-S(=O)2-基，可列舉例如：甲基磺醯基、乙基磺醯基、正丙基磺醯基、異丙基磺醯基、正丁基磺醯基、異丁基磺醯基、第二丁基磺醯基、第三丁基磺醯基、戊基磺醯基或己基磺醯基等基。 In the present invention, the so-called "C 1 to C 6 alkylsulfonyl" refers to the (C 1 to C 6 alkyl)-S(=O) 2 -group in which the alkyl part has the above meaning unless otherwise specified. , For example: methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, second butylsulfonate Acyl, tert-butylsulfonyl, pentylsulfonyl or hexylsulfonyl and other groups.

於本發明中所謂「C1至C6鹵烷基硫基」在無特別限定下係表示鹵烷基部分為上述意義之(C1至C6鹵烷基)-S-基，可列舉例如：氟甲基硫基、二氟甲基硫基、三氟甲基硫基、三氯甲基硫基、2,2,2-三氟乙基硫基、五氟乙基硫基、2,2,2-三氯乙基硫基、3,3,3-三氟丙基硫基、1,1,2,3,3,3-六氟丙基硫基、七氟丙基硫基、1,1,1,3,3,3-六氟丙烷-2-基硫基、七氟丙烷-2-基硫基或4,4,4-三氟丁基硫基等基。 In the present invention, the so-called "C 1 to C 6 haloalkylthio group" means that the haloalkyl part is the (C 1 to C 6 haloalkyl)-S- group in the above meaning without particular limitation, and examples include : Fluoromethylthio, difluoromethylthio, trifluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, pentafluoroethylthio, 2, 2,2-trichloroethylthio, 3,3,3-trifluoropropylthio, 1,1,2,3,3,3-hexafluoropropylthio, heptafluoropropylthio, 1,1,1,3,3,3-Hexafluoropropane-2-ylsulfanyl, heptafluoropropane-2-ylsulfanyl or 4,4,4-trifluorobutylsulfanyl and other groups.

於本發明中所謂「C1至C6鹵烷基亞磺醯基」在無特別限定下係表示鹵烷基部分為上述意義之(C1至C6鹵烷基)-S(=O)-基，可列舉例 如：二氟甲基亞磺醯基、三氟甲基亞磺醯基、三氯甲基亞磺醯基、2,2,2-三氟乙基亞磺醯基、2,2,2-三氯乙基亞磺醯基、五氟乙基亞磺醯基、3,3,3-三氟丙基亞磺醯基、七氟丙基亞磺醯基或七氟-2-丙基亞磺醯基等基。 In the present invention, the so-called "C 1 to C 6 haloalkylsulfinyl" group means that the haloalkyl part has the above meaning (C 1 to C 6 haloalkyl)-S(=O) -Group, for example: difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2 ,2,2-trichloroethylsulfinyl, pentafluoroethylsulfinyl, 3,3,3-trifluoropropylsulfinyl, heptafluoropropylsulfinyl or heptafluoro- 2-propylsulfinyl and other groups.

於本發明中所謂「C1至C6鹵烷基磺醯基」在無特別限定下係表示鹵烷基部分為上述意義之(C1至C6鹵烷基)-S(=O)2-基，可列舉例如：二氟甲基磺醯基、三氟甲基磺醯基、三氯甲基磺醯基、2,2,2-三氟乙基磺醯基、五氟乙基磺醯基、3,3,3-三氟丙基磺醯基、七氟丙基磺醯基、或七氟-2-丙基磺醯基等基。 In the present invention, the so-called "C 1 to C 6 haloalkylsulfonyl" means that the haloalkyl part has the above meaning (C 1 to C 6 haloalkyl)-S(=O) 2 -Group, for example: difluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, pentafluoroethylsulfonate Acyl, 3,3,3-trifluoropropylsulfonyl, heptafluoropropylsulfonyl, or heptafluoro-2-propylsulfonyl and other groups.

於本發明中所謂「C2至C6烯基硫基」在無特別限定下係表示烯基部分為上述意義之(C2至C6烯基)-S-基，可列舉例如：2-丙烯基硫基、2-丁烯基硫基、3-丁烯基硫基、2-戊烯基硫基、3-戊烯基硫基、4-戊烯基硫基、2-甲基-2-丁烯基硫基、2,4-戊二烯基硫基、2-己烯基硫基、3-己烯基硫基、4-己烯基硫基、5-己烯基硫基或2,4-己二烯基硫基等基。 In the present invention, the so-called "C 2 to C 6 alkenylthio group" means that the alkenyl moiety is (C 2 to C 6 alkenyl)-S- group in the above meaning without particular limitation, and examples include: 2- Propylenethio, 2-butenylthio, 3-butenylthio, 2-pentenylthio, 3-pentenylthio, 4-pentenylthio, 2-methyl- 2-butenylthio, 2,4-pentadienylthio, 2-hexenylthio, 3-hexenylthio, 4-hexenylthio, 5-hexenylthio Or 2,4-hexadienylthio and other groups.

於本發明中所謂「C2至C6烯基亞磺醯基」在無特別限定下係表示烯基部分為上述意義之(C2至C6烯基)-S(=O)-基，可列舉例如：2-丙烯基亞磺醯基、2-丁烯基亞磺醯基、3-丁烯基亞磺醯基、2-戊烯基亞磺醯基、3-戊烯基亞磺醯基、4-戊烯基亞磺醯基、2-甲基-2-丁烯基亞磺醯基、2,4-戊二烯基亞磺醯基、2-己烯基亞磺醯基、3-己烯基亞磺醯基、4-己烯基亞磺醯基、5-己烯基亞磺醯基或2,4-己二烯基亞磺醯基等基。 In the present invention, the so-called "C 2 to C 6 alkenylsulfinyl" means that the alkenyl part is the (C 2 to C 6 alkenyl)-S(=O)- group in the above meaning unless otherwise specified. For example, 2-propenyl sulfenyl group, 2-butenyl sulfinyl group, 3-butenyl sulfinyl group, 2-pentenyl sulfinyl group, 3-pentenyl sulfinyl group Acyl, 4-pentenylsulfinyl, 2-methyl-2-butenylsulfinyl, 2,4-pentadienylsulfinyl, 2-hexenylsulfinyl , 3-hexenyl sulfenyl, 4-hexenyl sulfenyl, 5-hexenyl sulfenyl or 2,4-hexadienyl sulfenyl and other groups.

於本發明中所謂「C2至C6烯基磺醯基」在無特別限定下係表示烯基部分為上述意義之(C2至C6烯基)-S(=O)2-基，可列舉例如：2-丙烯基磺醯基、2-丁烯基磺醯基、3-丁烯基磺醯基、2-戊烯基磺醯基、3-戊烯 基磺醯基、4-戊烯基磺醯基、2-甲基-2-丁烯基磺醯基、2,4-戊二烯基磺醯基、2-己烯基磺醯基、3-己烯基磺醯基、4-己烯基磺醯基、5-己烯基磺醯基或2,4-己二烯基磺醯基等基。 In the present invention, the so-called "C 2 to C 6 alkenylsulfonyl" means that the alkenyl part is the (C 2 to C 6 alkenyl)-S(=O) 2 -group in the above meaning unless otherwise specified. For example, 2-propenylsulfonyl, 2-butenylsulfonyl, 3-butenylsulfonyl, 2-pentenylsulfonyl, 3-pentenylsulfonyl, 4- Pentenylsulfonyl, 2-methyl-2-butenylsulfonyl, 2,4-pentadienylsulfonyl, 2-hexenylsulfonyl, 3-hexenylsulfonyl , 4-hexenylsulfonyl, 5-hexenylsulfonyl or 2,4-hexadienylsulfonyl and other groups.

於本發明中所謂「C2至C6鹵烯基硫基」在無特別限定下係表示烯基部分為上述意義之(C2至C6鹵烯基)-S-基，可列舉例如：3-氯-2-丙烯基硫基、3,3-二氯-2-丙烯基硫基、3,3-二氟-2-丙烯基硫基、3,3,3-三氟-1-丙烯基硫基、2,3,3,3-四氟-1-丙烯基硫基、4,4,4-三氟-2-丁烯基硫基、3,4,4-三氟-3-丁烯基硫基、5-氯-3-戊烯基硫基或6-氟-2-己烯基硫基等基。 In the present invention, the so-called "C 2 to C 6 haloalkenylthio group" means that the alkenyl moiety is (C 2 to C 6 haloalkenyl)-S- group without any particular limitation, and examples include: 3-chloro-2-propenylthio, 3,3-dichloro-2-propenylthio, 3,3-difluoro-2-propenylthio, 3,3,3-trifluoro-1- Propylenethio, 2,3,3,3-tetrafluoro-1-propenylthio, 4,4,4-trifluoro-2-butenylthio, 3,4,4-trifluoro-3 -Butenylthio, 5-chloro-3-pentenylthio or 6-fluoro-2-hexenylthio and other groups.

於本發明中所謂「C2至C6鹵烯基亞磺醯基」在無特別限定下係表示烯基部分為上述意義之(C2至C6鹵烯基)-S(=O)-基，可列舉例如：3-氯-2-丙烯基亞磺醯基、3,3-二氯-2-丙烯基亞磺醯基、3,3-二氟-2-丙烯基亞磺醯基、3,3,3-三氟-1-丙烯基亞磺醯基、2,3,3,3-四氟-1-丙烯基亞磺醯基、4,4,4-三氟-2-丁烯基亞磺醯基、3,4,4-三氟-3-丁烯基亞磺醯基、5-氯-3-戊烯基亞磺醯基或6-氟-2-己烯基亞磺醯基等基。 In the present invention, the so-called "C 2 to C 6 haloalkenyl sulfenyl" means that the alkenyl part has the above meaning (C 2 to C 6 haloalkenyl) -S(=O)- Examples include: 3-chloro-2-propenylsulfinamide, 3,3-dichloro-2-propenylsulfinamide, 3,3-difluoro-2-propenylsulfinamide , 3,3,3-trifluoro-1-propenylsulfinyl, 2,3,3,3-tetrafluoro-1-propenylsulfinyl, 4,4,4-trifluoro-2- Butenylsulfinyl, 3,4,4-trifluoro-3-butenylsulfinyl, 5-chloro-3-pentenylsulfinyl or 6-fluoro-2-hexenyl Sulfonyl and other groups.

於本發明中所謂「C2至C6鹵烯基磺醯基」在無特別限定下係表示烯基部分為上述意義之(C2至C6鹵烯基)-S(=O)2-基，可列舉例如：3-氯-2-丙烯基磺醯基、3,3-二氯-2-丙烯基磺醯基、3,3-二氟-2-丙烯基磺醯基、3,3,3-三氟-1-丙烯基磺醯基、2,3,3,3-四氟-1-丙烯基磺醯基、4,4,4-三氟-2-丁烯基磺醯基、3,4,4-三氟-3-丁烯基磺醯基、5-氯-3-戊烯基磺醯基或6-氟-2-己烯基磺醯基等基。 In the present invention, the so-called "C 2 to C 6 haloalkenylsulfonyl" means that the alkenyl part has the above meaning (C 2 to C 6 haloalkenyl) -S(=O) 2- Examples include: 3-chloro-2-propenylsulfonyl, 3,3-dichloro-2-propenylsulfonyl, 3,3-difluoro-2-propenylsulfonyl, 3, 3,3-trifluoro-1-propenylsulfonyl, 2,3,3,3-tetrafluoro-1-propenylsulfonyl, 4,4,4-trifluoro-2-butenylsulfonyl Group, 3,4,4-trifluoro-3-butenylsulfonyl, 5-chloro-3-pentenylsulfonyl, 6-fluoro-2-hexenylsulfonyl and other groups.

於本發明中所謂「C2至C6炔基硫基」在無特別限定下係表示炔基部分為上述意義之(C2至C6炔基)-S-基，可列舉例如：丙炔基硫基、 1-丁炔-3-基硫基、3-甲基-1-丁炔-3-基硫基、2-丁炔基硫基、3-丁炔基硫基、2-戊炔基硫基、3-戊炔基硫基、4-戊炔基硫基或5-己炔基硫基等基。 In the present invention, the so-called "C 2 to C 6 alkynylthio group" means that the alkynyl part is (C 2 to C 6 alkynyl)-S- group in the above meaning without particular limitation, and examples include propyne Thio, 1-butyn-3-ylthio, 3-methyl-1-butyn-3-ylthio, 2-butynylthio, 3-butynylthio, 2-pentyl Groups such as alkynylthio, 3-pentynylthio, 4-pentynylthio or 5-hexynylthio.

於本發明中所謂「C2至C6炔基亞磺醯基」在無特別限定下係表示炔基部分為上述意義之(C2至C6炔基)-S(=O)-基，可列舉例如：丙炔基亞磺醯基、1-丁炔-3-基亞磺醯基、3-甲基-1-丁炔-3-基亞磺醯基、2-丁炔基亞磺醯基、3-丁炔基亞磺醯基、2-戊炔基亞磺醯基、3-戊炔基亞磺醯基、4-戊炔基亞磺醯基或5-己炔基亞磺醯基等基。 In the present invention, the so-called "C 2 to C 6 alkynylsulfinyl" group means that the alkynyl part is the (C 2 to C 6 alkynyl)-S(=O)- group in the above meaning unless otherwise specified. Examples include: propynylsulfinyl, 1-butyn-3-ylsulfinyl, 3-methyl-1-butyn-3-ylsulfinyl, 2-butynylsulfinyl Acyl, 3-butynylsulfinyl, 2-pentynylsulfinyl, 3-pentynylsulfinyl, 4-pentynylsulfinyl, or 5-hexynylsulfinyl Acyl and other bases.

於本發明中所謂「C2至C6炔基磺醯基」在無特別限定下係表示炔基部分為上述意義之(C2至C6炔基)-S(=O)2-基，可列舉例如：丙炔基磺醯基、1-丁炔-3-基磺醯基、3-甲基-1-丁炔-3-基磺醯基、2-丁炔基磺醯基、3-丁炔基磺醯基、2-戊炔基磺醯基、3-戊炔基磺醯基、4-戊炔基磺醯基或5-己炔基磺醯基等基。 In the present invention, the so-called "C 2 to C 6 alkynylsulfonyl" means that the alkynyl part is (C 2 to C 6 alkynyl)-S(=O) 2 -group, which has the above meaning, without particular limitation, Examples include: propynylsulfonyl, 1-butyn-3-ylsulfonyl, 3-methyl-1-butyn-3-ylsulfonyl, 2-butynylsulfonyl, 3 -Butynylsulfonyl, 2-pentynylsulfonyl, 3-pentynylsulfonyl, 4-pentynylsulfonyl, 5-hexynylsulfonyl and other groups.

於本發明中所謂「C3至C6環烷基硫基」在無特別限定下係表示環烷基部分為上述意義之(C3至C6環烷基)-S-基，可列舉例如：環丙基硫基、環丁基硫基、環戊基硫基或環己基硫基等基。 In the present invention, the so-called "C 3 to C 6 cycloalkylthio group" means that the cycloalkyl moiety is the (C 3 to C 6 cycloalkyl)-S- group in the above meaning without particular limitation, and examples include : Cyclopropylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio and other groups.

於本發明中所謂「C3至C6環烷基亞磺醯基」在無特別限定下係表示環烷基部分為上述意義之(C3至C6環烷基)-S(=O)-基，可列舉例如：環丙基亞磺醯基、環丁基亞磺醯基、環戊基亞磺醯基或環己基亞磺醯基等基。 In the present invention, the so-called "C 3 to C 6 cycloalkylsulfinyl group" means that the cycloalkyl part has the above meaning (C 3 to C 6 cycloalkyl)-S(=O) unless otherwise specified. -Group includes, for example, cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, or cyclohexylsulfinyl.

於本發明中所謂「C3至C6環烷基磺醯基」在無特別限定下係表示環烷基部分為上述意義之(C3至C6環烷基)-S(=O)2-基，可列舉例如：環丙基磺醯基、環丁基磺醯基、環戊基磺醯基或環己基磺醯基等基。 In the present invention, the so-called "C 3 to C 6 cycloalkylsulfonyl" means that the cycloalkyl portion is (C 3 to C 6 cycloalkyl)-S(=O) 2 unless otherwise specified. -Group includes, for example, groups such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl.

於本發明中所謂「芳香族雜環硫基」在無特別限定下係表示芳香族雜環部分為上述意義之(芳香族雜環)-S-基，可列舉例如：吡啶-2-基硫基、吡啶-3-基硫基、吡啶-4-基硫基、吡

Figure 108129126-A0202-12-0039-137
-2-基硫基、嗒
Figure 108129126-A0202-12-0039-138
-3-基硫基、嗒
Figure 108129126-A0202-12-0039-139
-4-基硫基、嘧啶-2-基硫基、嘧啶-4-基硫基、嘧啶-5-基硫基、噻唑-2-基硫基、噻唑-4-基硫基或噻唑-5-基硫基等基。 In the present invention, the "aromatic heterocyclic thio group" means that the aromatic heterocyclic moiety is the (aromatic heterocyclic)-S- group in the above meaning without particular limitation, and examples include pyridin-2-ylsulfide , Pyridin-3-ylthio, pyridin-4-ylthio, pyridine
Figure 108129126-A0202-12-0039-137
-2-ylthio
Figure 108129126-A0202-12-0039-138
-3-ylthio
Figure 108129126-A0202-12-0039-139
-4-ylthio, pyrimidin-2-ylthio, pyrimidin-4-ylthio, pyrimidin-5-ylthio, thiazol-2-ylthio, thiazol-4-ylthio or thiazole-5 -Base thio and other bases.

於本發明中所謂「芳香族雜環亞磺醯基」在無特別限定下係表示芳香族雜環部分為上述意義之(芳香族雜環)-S(=O)-基，可列舉例如：吡啶-2-基亞磺醯基、吡啶-3-基亞磺醯基、吡啶-4-基亞磺醯基、吡

Figure 108129126-A0202-12-0039-140
-2-基亞磺醯基、嗒
Figure 108129126-A0202-12-0039-141
-3-基亞磺醯基、嗒
Figure 108129126-A0202-12-0039-142
-4-基亞磺醯基、嘧啶-2-基亞磺醯基、嘧啶-4-基亞磺醯基、嘧啶-5-基亞磺醯基、噻唑-2-基亞磺醯基、噻唑-4-基亞磺醯基或噻唑-5-基亞磺醯基等基。 In the present invention, the term "aromatic heterocyclic sulfenyl" means that the aromatic heterocyclic moiety is the (aromatic heterocyclic)-S(=O)- group in the above meaning without particular limitation. Examples include: Pyridin-2-ylsulfinyl, pyridin-3-ylsulfinyl, pyridin-4-ylsulfinyl, pyridine
Figure 108129126-A0202-12-0039-140
-2-ylsulfinyl, ta
Figure 108129126-A0202-12-0039-141
-3-ylsulfinyl, ta
Figure 108129126-A0202-12-0039-142
-4-ylsulfinyl, pyrimidin-2-ylsulfinyl, pyrimidin-4-ylsulfinyl, pyrimidin-5-ylsulfinyl, thiazol-2-ylsulfinyl, thiazole Groups such as -4-ylsulfinyl or thiazol-5-ylsulfinyl.

於本發明中所謂「芳香族雜環磺醯基」在無特別限定下係表示芳香族雜環部分為上述意義之(芳香族雜環)-S(=O)2-基，可列舉例如：吡啶-2-基磺醯基、吡啶-3-基磺醯基、吡啶-4-基磺醯基、吡

Figure 108129126-A0202-12-0039-143
-2-基磺醯基、嗒
Figure 108129126-A0202-12-0039-145
-3-基磺醯基、嗒
Figure 108129126-A0202-12-0039-167
-4-基磺醯基、嘧啶-2-基磺醯基、嘧啶-4-基磺醯基、嘧啶-5-基磺醯基、噻唑-2-基磺醯基、噻唑-4-基磺醯基或噻唑-5-基磺醯基等基。 In the present invention, the "aromatic heterocyclic sulfonyl group" means that the aromatic heterocyclic moiety is the (aromatic heterocyclic)-S(=O) 2 -group in the above meaning without particular limitation, and examples include: Pyridin-2-ylsulfonyl, pyridin-3-ylsulfonyl, pyridin-4-ylsulfonyl, pyridine
Figure 108129126-A0202-12-0039-143
-2-yl sulfonamide, ta
Figure 108129126-A0202-12-0039-145
-3-ylsulfonyl
Figure 108129126-A0202-12-0039-167
-4-ylsulfonyl, pyrimidin-2-ylsulfonyl, pyrimidin-4-ylsulfonyl, pyrimidin-5-ylsulfonyl, thiazol-2-ylsulfonyl, thiazol-4-ylsulfon Acyl or thiazol-5-ylsulfonyl and other groups.

於本發明中所謂「飽和雜環硫基」在無特別限定下係表示飽和雜環部分為上述意義之(飽和雜環)-S-基，可列舉例如：氧環丁烷-3-基硫基、四氫呋喃-2-基硫基、四氫呋喃-3-基硫基、(四氫-2H-哌喃-2-基)硫基、(四氫-2H-哌喃-3-基)硫基或(四氫-2H-哌喃-4-基)硫基等基。 In the present invention, the "saturated heterocyclic thio group" means that the saturated heterocyclic moiety is a (saturated heterocyclic)-S- group in the above meaning unless otherwise specified, and examples include: oxocyclobutane-3-yl sulfide Group, tetrahydrofuran-2-ylthio, tetrahydrofuran-3-ylthio, (tetrahydro-2H-piperan-2-yl)thio, (tetrahydro-2H-piperan-3-yl)thio or (Tetrahydro-2H-piperan-4-yl)thio and other groups.

於本發明中所謂「飽和雜環亞磺醯基」在無特別限定下係表示飽和雜環部分為上述意義之(飽和雜環)-S(=O)-基，可列舉例如：氧環丁烷-3-基亞磺醯基、四氫呋喃-2-基亞磺醯基、四氫呋喃-3-基亞磺醯基、(四氫-2H-哌喃-2-基)亞磺醯基、(四氫-2H-哌喃-3-基)亞磺醯基或(四氫-2H-哌喃-4-基)亞磺醯基等基。 In the present invention, the "saturated heterocyclic sulfinyl group" means that the saturated heterocyclic moiety is a (saturated heterocyclic)-S(=O)- group of the above meaning without particular limitation, and examples include oxetane Alkan-3-ylsulfinyl, tetrahydrofuran-2-ylsulfinyl, tetrahydrofuran-3-ylsulfinyl, (tetrahydro-2H-piperan-2-yl)sulfinyl, (four Hydrogen-2H-piperan-3-yl)sulfinyl or (tetrahydro-2H-piperan-4-yl)sulfinyl and other groups.

於本發明中所謂「飽和雜環磺醯基」在無特別限定下係表示飽和雜環部分為上述意義之(飽和雜環)-S(=O)2-基，可列舉例如：氧環丁烷-3-基磺醯基、四氫呋喃-2-基磺醯基、四氫呋喃-3-基磺醯基、(四氫-2H-哌喃-2-基)磺醯基、(四氫-2H-哌喃-3-基)磺醯基或(四氫-2H-哌喃-4-基)磺醯基等基。 In the present invention, the "saturated heterocyclic sulfonyl group" means that the saturated heterocyclic moiety is a (saturated heterocyclic)-S(=O) 2 -group of the above meaning without particular limitation, and examples include oxetane Alkyl-3-ylsulfonyl, tetrahydrofuran-2-ylsulfonyl, tetrahydrofuran-3-ylsulfonyl, (tetrahydro-2H-piperan-2-yl)sulfonyl, (tetrahydro-2H- Piperan-3-yl)sulfonyl or (tetrahydro-2H-piperan-4-yl)sulfonyl and other groups.

於本發明中所謂「C1至C6烷氧基C1至C6烷基」在無特別限定下係表示烷氧基部分及烷基部分為上述意義之(C1至C6烷氧基)-(C1至C6烷基)，可列舉例如：甲氧基甲基、乙氧基甲基、正丙氧基甲基、異丙氧基甲基、第三丁氧基甲基、1-甲氧基乙基、1-甲氧基-1-甲基乙基、2-甲氧基乙基、1-乙氧基乙基、2-乙氧基乙基、2-異丙氧基乙基、3-甲氧基丙基、2-甲氧基丙基、3-乙氧基丙基、4-甲氧基丁基或4-乙氧基丁基等基。 In the present invention, the so-called "C 1 to C 6 alkoxy C 1 to C 6 alkyl" means that the alkoxy part and the alkyl part have the above meanings without particular limitation (C 1 to C 6 alkoxy )-(C 1 to C 6 alkyl), for example: methoxymethyl, ethoxymethyl, n-propoxymethyl, isopropoxymethyl, third butoxymethyl, 1-methoxyethyl, 1-methoxy-1-methylethyl, 2-methoxyethyl, 1-ethoxyethyl, 2-ethoxyethyl, 2-isopropoxy Groups such as ethyl, 3-methoxypropyl, 2-methoxypropyl, 3-ethoxypropyl, 4-methoxybutyl or 4-ethoxybutyl.

於本發明中所謂「C1至C6烷基硫基C1至C6烷基」在無特別限定下係表示烷基硫基部分及烷基部分為上述意義之(C1至C6烷基硫基)-(C1至C6烷基)，可列舉例如：甲基硫基甲基、2-(甲基硫基)乙基、3-(甲基硫基)丙基、4-(甲基硫基)丁基、乙基硫基甲基、丙基硫基甲基、丁基硫基甲基或戊基硫基甲基等基。 In the present invention, the term "C 1 to C 6 alkylthio C 1 to C 6 alkyl" means, without particular limitation, that the alkylthio moiety and the alkyl moiety have the above meaning (C 1 to C 6 alkyl Alkylthio)-(C 1 to C 6 alkyl), for example, methylthiomethyl, 2-(methylthio)ethyl, 3-(methylthio)propyl, 4- Groups such as (methylthio)butyl, ethylthiomethyl, propylthiomethyl, butylthiomethyl, or pentylthiomethyl.

於本發明中所謂「氰基C1至C6烷基」在無特別限定下係表示烷基部分為上述意義之(氰基)-(C1至C6烷基)，可列舉例如：氰基甲基、1-氰基乙基、2-氰基乙基、3-氰基丙基、2-氰基丙烷-2-基、1-氰基丁基、4-氰基丁基、5-氰基戊基或6-氰基己基等基。 In the present invention, the term "cyano C 1 to C 6 alkyl" means that the alkyl portion is (cyano)-(C 1 to C 6 alkyl) in the above meaning without particular limitation, and examples include: cyano Methyl, 1-cyanoethyl, 2-cyanoethyl, 3-cyanopropyl, 2-cyanopropan-2-yl, 1-cyanobutyl, 4-cyanobutyl, 5 -Groups such as cyanopentyl or 6-cyanohexyl.

於本發明中所謂「苯基C1至C6烷基」，在無特別限定下係表示烷基部分為上述意義之苯基-(C1至C6烷基)，可列舉例如：苄基、1-苯基乙基、2-苯基乙基、3-苯基丙基、4-苯基丁基、5-苯基戊基或6-苯基己基等基。 In the present invention, the term "phenyl C 1 to C 6 alkyl" refers to the phenyl-(C 1 to C 6 alkyl) of the above-mentioned meaning without limitation, and examples include benzyl , 1-phenylethyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl or 6-phenylhexyl and other groups.

於本發明中所謂「苯基C1至C6烷氧基」，在無特別限定下係表示烷氧基部分為上述意義之苯基-(C1至C6烷氧基)，可列舉例如：苄基氧基、1-苯基乙氧基、2-苯基乙氧基、3-苯基丙氧基、4-苯基丁氧基、5-苯基戊氧基或6-苯基己氧基等基。 In the present invention, the term "phenyl C 1 to C 6 alkoxy" refers to phenyl-(C 1 to C 6 alkoxy), which means that the alkoxy part is the above-mentioned meaning, without particular limitation. : Benzyloxy, 1-phenylethoxy, 2-phenylethoxy, 3-phenylpropoxy, 4-phenylbutoxy, 5-phenylpentoxy or 6-phenyl Hexyloxy and other groups.

於本發明中所謂「芳香族雜環C1至C6烷基」在無特別限定下係表示芳香族雜環及烷基部分為上述意義之芳香族雜環-(C1至C6烷基)，可列舉例如：吡啶-2-基甲基、吡啶-3-基甲基、吡啶-4-基甲基、吡啶-2-基乙基、吡

Figure 108129126-A0202-12-0041-147
-2-基甲基、嗒
Figure 108129126-A0202-12-0041-148
-3-基甲基、嗒
Figure 108129126-A0202-12-0041-149
-4-基甲基、嘧啶-2-基甲基、嘧啶-4-基甲基、嘧啶-5-基甲基、噻唑-2-基甲基、噻唑-4-基甲基或噻唑-5-基甲基等基。 In the present invention, the term "aromatic heterocyclic C 1 to C 6 alkyl" refers to an aromatic heterocyclic ring and the alkyl portion is an aromatic heterocyclic ring having the above meaning -(C 1 to C 6 alkyl) ), for example: pyridin-2-ylmethyl, pyridin-3-ylmethyl, pyridin-4-ylmethyl, pyridin-2-ylethyl, pyridine
Figure 108129126-A0202-12-0041-147
-2-ylmethyl, ta
Figure 108129126-A0202-12-0041-148
-3-ylmethyl
Figure 108129126-A0202-12-0041-149
-4-ylmethyl, pyrimidin-2-ylmethyl, pyrimidin-4-ylmethyl, pyrimidin-5-ylmethyl, thiazol-2-ylmethyl, thiazol-4-ylmethyl or thiazole-5 -Methylmethyl and other groups.

於本發明中所謂「飽和雜環C1至C6烷基」在無特別限定下係表示飽和雜環及烷基部分為上述意義之飽和雜環-(C1至C6烷基)，可列舉例如：氧環丁烷-3-基甲基、四氫呋喃-2-基甲基、四氫呋喃-3-基甲基、(四 氫-2H-哌喃-2-基)甲基、(四氫-2H-哌喃-3-基)甲基或(四氫-2H-哌喃-4-基)甲基等基。 In the present invention, "saturated heterocyclic ring C 1 to C 6 alkyl" means a saturated heterocyclic ring and the alkyl part is a saturated heterocyclic ring-(C 1 to C 6 alkyl) of the above meaning unless otherwise specified. Examples include: oxycyclobutane-3-ylmethyl, tetrahydrofuran-2-ylmethyl, tetrahydrofuran-3-ylmethyl, (tetrahydro-2H-piperan-2-yl)methyl, (tetrahydro- 2H-piperan-3-yl)methyl or (tetrahydro-2H-piperan-4-yl)methyl and other groups.

於本發明中所謂「單(C1至C6烷基)胺基」在無特別限定下係表示烷基部分為上述意義之(C1至C6烷基)-NH-基，可列舉例如：甲基胺基、乙基胺基或正丙基胺基等基。 In the present invention, the so-called "mono(C 1 to C 6 alkyl)amino group" means that the alkyl portion is the (C 1 to C 6 alkyl)-NH- group in the above meaning without particular limitation, and examples include : Methylamino group, ethylamino group or n-propylamino group.

於本發明中所謂「二(C1至C6烷基)胺基」在無特別限定下係表示烷基部分為上述意義之(C1至C6烷基)2-N-基，2個烷基可彼此相異，可列舉例如：二甲基胺基、甲基乙基胺基或甲基正丙基胺基等基。 In the present invention, the so-called "di(C 1 to C 6 alkyl)amino group" means that the alkyl portion is the (C 1 to C 6 alkyl) 2 -N- group in the above meaning without limitation, 2 The alkyl groups may be different from each other, and examples thereof include groups such as dimethylamino, methylethylamino, and methyl-n-propylamino.

於本發明中所謂「C1至C6烷基羰基胺基」在無特別限定下係表示烷基部分為上述意義之(C1至C6烷基)-C(=O)-NH-基，可列舉例如：乙醯基胺基、丙醯基胺基、丁醯基胺基或異丁醯基胺基等基。 In the present invention, the so-called "C 1 to C 6 alkylcarbonylamino group" means that the alkyl portion is (C 1 to C 6 alkyl)-C(=O)-NH- group without any particular limitation. , Examples include groups such as an acetamido group, a propylamino group, a butylamino group, or an isobutylamino group.

於本發明中所謂「N-(C1至C6烷基羰基)-N-(C1至C6烷基)胺基」在無特別限定下係表示胺基的2個氫原子分別經(C1至C6烷基)-C(=O)-基及(C1至C6烷基)-基取代之基，可列舉例如：N-甲基乙醯基胺基、N-甲基丙醯基胺基、N-甲基丁醯基胺基或N-甲基異丁醯基胺基等基。 In the present invention, the so-called "N-(C 1 to C 6 alkylcarbonyl)-N-(C 1 to C 6 alkyl)amino group" means, without particular limitation, that two hydrogen atoms of the amine group respectively pass ( C 1 to C 6 alkyl)-C(=O)- group and (C 1 to C 6 alkyl)- group substituted groups, for example: N-methylacetamide, N-methyl Groups such as acrylamino, N-methylbutylamide, or N-methylisobutylamide.

於本發明中所謂「C1至C6烷氧基羰基胺基」在無特別限定下係表示烷氧基部分為上述意義之(C1至C6烷氧基)-C(=O)-NH-基，可列舉例如：甲氧基羰基胺基、乙氧基羰基胺基、正丙氧基羰基胺基或異丙氧基羰基胺基等基。 In the present invention, the so-called "C 1 to C 6 alkoxycarbonylamino group" means that (C 1 to C 6 alkoxy)-C(=O)- Examples of the NH- group include a methoxycarbonylamino group, an ethoxycarbonylamino group, an n-propoxycarbonylamino group, or an isopropoxycarbonylamino group.

於本發明中所謂「N-(C1至C6烷氧基羰基)-N-(C1至C6烷基)胺基」在無特別限定下係表示胺基的2個氫原子分別經(C1至C6烷氧基)-C(=O)-基及(C1至C6烷基)-基取代之基，可列舉例如：甲氧基羰基-(N- 甲基)-胺基、乙氧基羰基-(N-甲基)-胺基、正丙氧基羰基-(N-甲基)-胺基或異丙氧基羰基-(N-甲基)-胺基等基。 In the present invention, the so-called "N-(C 1 to C 6 alkoxycarbonyl)-N-(C 1 to C 6 alkyl)amino group" means, without particular limitation, that the two hydrogen atoms of the amine group pass through The group substituted by (C 1 to C 6 alkoxy)-C(=O)- group and (C 1 to C 6 alkyl)- group can be exemplified by methoxycarbonyl-(N-methyl)- Amino, ethoxycarbonyl-(N-methyl)-amino, n-propoxycarbonyl-(N-methyl)-amino or isopropoxycarbonyl-(N-methyl)-amino, etc. base.

於本發明中所謂「C1至C6烷基磺醯基胺基」在無特別限定下係表示烷基部分為上述意義之(C1至C6烷基)-S(=O)2-NH-基，可列舉例如：甲基磺醯基胺基、乙基磺醯基胺基、正丙基磺醯基胺基、異丙基磺醯基胺基或第三丁基磺醯基胺基等基。 In the present invention, the so-called "C 1 to C 6 alkylsulfonylamino group" means that (C 1 to C 6 alkyl)-S(=O) 2- NH- group, for example, methylsulfonamide, ethylsulfonamide, n-propylsulfonamide, isopropylsulfonamide, or tert-butylsulfonamide基等基。 Base and other base.

於本發明中所謂「N-(C1至C6烷基磺醯基)-N-(C1至C6烷基)胺基」在無特別限定下係表示胺基的2個氫原子分別經(C1至C6烷基)-S(=O)2-基及(C1至C6烷基)-基取代之基，可列舉例如：N-甲基甲基磺醯基胺基、N-甲基乙基磺醯基胺基、N-甲基正丙基磺醯基胺基、N-甲基異丙基磺醯基胺基或N-甲基第三丁基磺醯基胺基等基。 In the present invention, the so-called "N-(C 1 to C 6 alkylsulfonyl)-N-(C 1 to C 6 alkyl)amino group" means, without particular limitation, two hydrogen atoms of the amine group The group substituted with (C 1 to C 6 alkyl)-S(=O) 2 -group and (C 1 to C 6 alkyl)- group can be exemplified by N-methylmethylsulfonylamino group , N-methyl ethyl sulfonamide, N-methyl n-propyl sulfonamide, N-methyl isopropyl sulfonamide, or N-methyl tertiary butyl sulfonamide Amine and other groups.

於本發明中所謂「C1至C6鹵烷基磺醯基胺基」在無特別限定下係表示鹵烷基部分為上述意義之(C1至C6鹵烷基)-S(=O)2-NH-基，可列舉例如：氟甲基磺醯基胺基、二氟甲基磺醯基胺基、三氟甲基磺醯基胺基、氯甲基磺醯基胺基、三氯甲基磺醯基胺基、2,2,2-三氟乙基磺醯基胺基、2,2-二氟乙基磺醯基胺基或3,3,3-三氟丙基磺醯基胺基等基。 In the present invention, the so-called "C 1 to C 6 haloalkylsulfonylamino group" means that the haloalkyl part has the above meaning (C 1 to C 6 haloalkyl)-S(=O ) 2 -NH- group, for example: fluoromethylsulfonylamino group, difluoromethylsulfonylamino group, trifluoromethylsulfonylamino group, chloromethylsulfonylamino group, tris Chloromethylsulfonamide, 2,2,2-trifluoroethylsulfonamide, 2,2-difluoroethylsulfonamide, or 3,3,3-trifluoropropylsulfonate Acylamino and other groups.

於本發明中所謂「N-(C1至C6鹵烷基磺醯基)-N-(C1至C6烷基)胺基」在無特別限定下係表示胺基的2個氫原子分別經(C1至C6鹵烷基)-S(=O)2-基及(C1至C6烷基)-基取代之基，可列舉例如：N-甲基氟甲基磺醯基胺基、N-甲基二氟甲基磺醯基胺基、N-甲基三氟甲基磺醯基胺基、N-甲基氯甲基磺醯基胺基、N-甲基三氯甲基磺醯基胺基、N-甲基-2,2,2-三 氟乙基磺醯基胺基、N-甲基-2,2-二氟乙基磺醯基胺基或N-甲基-3,3,3-三氟丙基磺醯基胺基等基。 In the present invention, the so-called "N-(C 1 to C 6 haloalkylsulfonyl)-N-(C 1 to C 6 alkyl)amino group" means 2 hydrogen atoms of the amine group without particular limitation Groups substituted with (C 1 to C 6 haloalkyl)-S(=O) 2 -groups and (C 1 to C 6 alkyl)- groups, respectively, for example: N-methylfluoromethylsulfonamide Aminoamino, N-methyldifluoromethylsulfonylamino, N-methyltrifluoromethylsulfonylamino, N-methylchloromethylsulfonylamino, N-methyltris Chloromethylsulfonamide, N-methyl-2,2,2-trifluoroethylsulfonamide, N-methyl-2,2-difluoroethylsulfonamide or N -Methyl-3,3,3-trifluoropropylsulfonylamino and other groups.

於本發明中所謂「單(C1至C6烷基)胺基羰基」在無特別限定下係表示烷基部分為上述意義之(C1至C6烷基)-NH-C(=O)-基，可列舉例如：甲基胺基羰基、乙基胺基羰基、丙基胺基羰基或異丙基胺基羰基等基。 In the present invention, the so-called "mono(C 1 to C 6 alkyl)aminocarbonyl group" means that (C 1 to C 6 alkyl)-NH-C(=O )- group, for example, a group such as methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, or isopropylaminocarbonyl.

於本發明中所謂「二(C1至C6烷基)胺基羰基」在無特別限定下係表示烷基部分為上述意義之(C1至C6烷基)2-N-C(=O)-基、2個烷基可彼此相異，可列舉例如：二甲基胺基羰基、二乙基胺基羰基或二異丙基胺基羰基等基。 In the present invention, the so-called "di(C 1 to C 6 alkyl)aminocarbonyl group" means that the alkyl portion is (C 1 to C 6 alkyl) 2 -NC(=O) unless otherwise specified. -Group and two alkyl groups may be different from each other, and examples thereof include groups such as dimethylaminocarbonyl, diethylaminocarbonyl, or diisopropylaminocarbonyl.

於本發明中所謂「單(C1至C6鹵烷基)胺基羰基」在無特別限定下係表示鹵烷基部分為上述意義之(C1至C6鹵烷基)-NH-C(=O)-基，可列舉例如：2-氟乙基胺基羰基、2,2,2-三氟乙基胺基羰基、2,2,2-三氯乙基胺基羰基或1,1,1,3,3,3-六氟-2-丙基胺基羰基等基。 In the present invention, the term "mono(C 1 to C 6 haloalkyl)aminocarbonyl" means that the haloalkyl part is of the above meaning (C 1 to C 6 haloalkyl)-NH-C, without particular limitation. (=O)- group, for example: 2-fluoroethylaminocarbonyl, 2,2,2-trifluoroethylaminocarbonyl, 2,2,2-trichloroethylaminocarbonyl or 1, 1,1,3,3,3-hexafluoro-2-propylaminocarbonyl and other groups.

於本發明中所謂「經R7任意地取代之C1至C6烷基」、「經R13任意地取代之C1至C6烷基」等標示係表示與碳原子鍵結之氫原子經任意的R7或R13取代之烷基，進行取代之R7或R13的數目可在各自指定的碳原子數範圍內任意地選擇。烷基上的取代基R7或R13存在有2個以上時，各R7或R13可彼此相同或彼此相異。 Labeling system in the present invention so-called "optionally substituted by R 7 of a C 1 to C 6 alkyl", "optionally substituted by R 13 of a C 1 to C 6 alkyl group" and the like denotes knot carbon atom bonded hydrogen atoms The number of the substituted R 7 or R 13 alkyl group and the number of the substituted R 7 or R 13 can be arbitrarily selected within the range of the designated number of carbon atoms. When there are two or more substituents R 7 or R 13 on the alkyl group, each R 7 or R 13 may be the same as or different from each other.

於本發明中所謂「經R13任意地取代之C1至C6鹵烷基」等標示係表示與碳原子鍵結之氫原子經任意的R13取代之鹵烷基，進行取代 之R13的數目可在各自指定的碳原子數範圍內任意地選擇。於鹵烷基上的取代基R13存在有2個以上時，各R13可彼此相同或彼此相異。 The present invention is based on the so-called denoted "substituents of R 13 optionally via a C 1 to C 6 haloalkyl", etc. represents a carbon atom knot hydrogen atoms substituted with any of R 13 haloalkyl, the substituent R 13 for The number of can be arbitrarily selected within the range of the number of carbon atoms designated by each. When there are two or more substituents R 13 on the haloalkyl group, each R 13 may be the same as or different from each other.

於本發明中所謂「經R8任意地取代之C3至C6環烷基」等標示係表示與碳原子鍵結之氫原子經任意的R8取代之環烷基，進行取代之R8的數目可在各自指定的碳原子數範圍內任意地選擇。於環烷基上的取代基R8存在有2個以上時，各R8可彼此相同或彼此相異。 In the present invention, the so-called “C 3 to C 6 cycloalkyl optionally substituted by R 8 ”and the like indicate that the hydrogen atom bonded to the carbon atom is substituted by an arbitrary R 8 , and the substituted R 8 The number of can be arbitrarily selected within the range of the number of carbon atoms designated by each. When there are two or more substituents R 8 on the cycloalkyl group, each R 8 may be the same as or different from each other.

於本發明中所謂「經R13任意地取代之C2至C6烯基」等標示係表示與碳原子鍵結之氫原子經任意的R13取代之烯基，進行取代之R13的數目可在各自指定的碳原子數範圍內任意地選擇。於烯基上的取代基R13存在有2個以上時，各R13可彼此相同或彼此相異。 In the present invention, marked lines called "through R 13 is optionally substituted with of C 2 to C 6 alkenyl group", etc. represented by the junction of the carbon atom bonded hydrogen atoms are any of R 13 substituents of the alkenyl group, for the number of substituents of R 13 is It can be arbitrarily selected within the range of the number of carbon atoms designated by each. When there are two or more substituents R 13 on the alkenyl group, each R 13 may be the same as or different from each other.

於本發明中所謂「經R13任意地取代之C2至C6炔基」等標示係表示與碳原子鍵結之氫原子經任意的R13任意地取代之炔基，進行取代之R13的數目可在各自指定的碳原子數範圍內任意地選擇。於炔基上的取代基R13存在有2個以上時，各R13可彼此相同或彼此相異。 In the present invention, the so-called "C 2 to C 6 alkynyl group optionally substituted by R 13 "and the like refer to an alkynyl group optionally substituted by an arbitrary R 13 for a hydrogen atom bonded to a carbon atom, and the substituted R 13 The number of can be arbitrarily selected within the range of the number of carbon atoms designated by each. When there are two or more substituents R 13 on the alkynyl group, each R 13 may be the same as or different from each other.

於本發明中所謂「經R7任意地取代之C1至C6烷氧基」、「經R13任意地取代之C1至C6烷氧基」等標示係表示與碳原子鍵結之氫原子經任意的R7或R13取代之烷氧基，進行取代之R7或R13的數目可在各自指定的碳原子數範圍內任意地選擇。於烷氧基上的取代基R7或R13存在有2個以上時，各R7或R13可彼此相同或彼此相異。 In the present invention, the term "optionally substituted by R 7 of a C 1 to C 6 alkoxy", "optionally substituted by the R 13 is a C 1 to C 6 alkoxy" etc. represents a carbon atom marked lines of bonded The alkoxy group in which the hydrogen atom is substituted by any R 7 or R 13 , and the number of R 7 or R 13 to be substituted can be arbitrarily selected within the range of the number of carbon atoms designated by each. When there are two or more substituents R 7 or R 13 on the alkoxy group, each R 7 or R 13 may be the same as or different from each other.

於本發明中所謂「經R13任意地取代之C1至C6鹵烷氧基」等標示係表示與碳原子鍵結之氫原子經任意的R13取代之鹵烷氧基，進行 取代之R13的數目可在各自指定的碳原子數範圍內任意地選擇。於鹵烷氧基上的取代基R13存在有2個以上時，各R13可彼此相同或彼此相異。 In the present invention, the so-called “C 1 to C 6 haloalkoxy optionally substituted by R 13 ”means that the hydrogen atom bonded to the carbon atom is substituted by haloalkoxy substituted by any R 13 . The number of R 13 can be arbitrarily selected within the range of the number of carbon atoms designated by each. When there are two or more substituents R 13 on the haloalkoxy group, each R 13 may be the same as or different from each other.

於本發明中所謂「經R13任意地取代之C1至C6烷基硫基」等標示係表示與碳原子鍵結之氫原子經任意的R13取代之烷基硫基，進行取代之R13的數目可在各自指定的碳原子數範圍內任意地選擇。於烷基硫基上的取代基R13存在有2個以上時，各R13可彼此相同或彼此相異。 In the present invention, the so-called "C 1 to C 6 alkylthio group optionally substituted with R 13 "and the like indicate that the hydrogen atom bonded to the carbon atom is substituted with an arbitrary R 13 substituted alkylthio group. The number of R 13 can be arbitrarily selected within the range of the number of carbon atoms designated by each. When there are two or more substituents R 13 on the alkylthio group, each R 13 may be the same as or different from each other.

於本發明中所謂「經R13任意地取代之C1至C6烷基亞磺醯基」等標示係表示與碳原子鍵結之氫原子經任意的R13取代之烷基亞磺醯基，進行取代之R13的數目可在各自指定的碳原子數範圍內任意地選擇。於烷基亞磺醯基上的取代基R13存在有2個以上時，各R13可彼此相同或彼此相異。 In the present invention, the so-called "C 1 to C 6 alkylsulfinyl arbitrarily substituted with R 13 "or the like means an alkyl sulfinyl group in which a hydrogen atom bonded to a carbon atom is optionally substituted with R 13 The number of R 13 to be substituted can be arbitrarily selected within the range of the number of carbon atoms designated by each. When there are two or more substituents R 13 on the alkylsulfinyl group, each R 13 may be the same as or different from each other.

於本發明中所謂「經R13任意地取代之C1至C6烷基磺醯基」等標示係表示與碳原子鍵結之氫原子經任意的R13取代之烷基磺醯基，進行取代之R13的數目可在各自指定的碳原子數範圍內任意地選擇。烷基磺醯基上的取代基R13存在有2個以上時，各R13可彼此相同或彼此相異。 In the present invention, the so-called "C 1 to C 6 alkylsulfonyl arbitrarily substituted with R 13 "and other labels indicate an alkyl sulfonyl group in which a hydrogen atom bonded to a carbon atom is substituted with an arbitrary R 13 . The number of substituted R 13 can be arbitrarily selected within the range of the number of carbon atoms designated by each. When there are two or more substituents R 13 on the alkylsulfonyl group, each R 13 may be the same as or different from each other.

於本發明中所謂「經R13任意地取代之C1至C6鹵烷基硫基」等標示係表示與碳原子鍵結之氫原子經任意的R13取代之鹵烷基硫基，進行取代之R13的數目可在各自指定的碳原子數範圍內任意地選擇。於鹵烷基硫基上的取代基R13存在有2個以上時，各R13可彼此相同或彼此相異。 In the present invention, the so-called “C 1 to C 6 haloalkylthio group optionally substituted by R 13 ”indicates that the hydrogen atom bonded to the carbon atom is substituted by an haloalkylthio group optionally substituted by R 13 . The number of substituted R 13 can be arbitrarily selected within the range of the number of carbon atoms designated by each. When there are two or more substituents R 13 on the haloalkylthio group, each R 13 may be the same as or different from each other.

於本發明中所謂「經R13任意地取代之C1至C6鹵烷基亞磺醯基」等標示係表示與碳原子鍵結之氫原子經任意的R13取代之鹵烷基亞 磺醯基，進行取代之R13的數目可在各自指定的碳原子數範圍內任意地選擇。於鹵烷基亞磺醯基上的取代基R13存在有2個以上時，各R13可彼此相同或彼此相異。 In the present invention, the so-called "C 1 to C 6 haloalkylsulfinylsulfonyl group optionally substituted by R 13 "means that the hydrogen atom bonded to the carbon atom is optionally substituted by haloalkylsulfinyl group R 13 The number of the substituted aryl group and R 13 can be arbitrarily selected within the range of the number of carbon atoms designated by each. When there are two or more substituents R 13 on the haloalkylsulfinyl group, each R 13 may be the same as or different from each other.

於本發明中所謂「經R13任意地取代之C1至C6鹵烷基磺醯基」等標示係表示與碳原子鍵結之氫原子經任意的R13取代之鹵烷基磺醯基，進行取代之R13的數目可在各自指定的碳原子數範圍內任意地選擇。於鹵烷基磺醯基上的取代基R13存在有2個以上時，各R13可彼此相同或彼此相異。 In the present invention, the so-called "C 1 to C 6 haloalkylsulfonyl arbitrarily substituted with R 13 "and the like means that the hydrogen atom bonded to the carbon atom is substituted with an arbitrary R 13 haloalkyl sulfonyl The number of R 13 to be substituted can be arbitrarily selected within the range of the number of carbon atoms designated by each. When there are two or more substituents R 13 on the haloalkylsulfonyl group, each R 13 may be the same as or different from each other.

於本發明中，[R1及R2可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子]、[R9及R10可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子]、[R11及R12可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子]或[R12及R14可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子]等標示之藉由該伸烷基鍵及與該伸烷基鍵相鄰接之原子所形成之雜環的具體例，可列舉例如：氮丙啶(Aziridine)、四氫吖唉(Azetidine)、吡咯啶(Pyrrolidine)、

Figure 108129126-A0202-12-0047-164
唑烷(Oxazolidine)、
Figure 108129126-A0202-12-0047-130
唑啉(Oxazoline)、異
Figure 108129126-A0202-12-0047-165
唑啉、四氫噻唑(Thiazolidine)、咪唑啶(Imidazolidine)、哌啶(Piperidine)、嗎啉(Morpholine)、硫代嗎啉(Thiomorpholine)、硫代嗎啉-1-氧化物、硫代嗎啉-1,1-二氧化物、哌
Figure 108129126-A0202-12-0047-132
(Piperazine)、六亞甲基亞胺(Homopiperidine)或七亞甲基亞胺等基。 In the present invention, [R 1 and R 2 may be bonded to each other to form a C 2 to C 6 alkylene bond, in which case the alkylene bond may contain 1 oxygen atom, sulfur atom or nitrogen atom], [ R 9 and R 10 may be bonded to each other to form a C 2 to C 6 alkylene bond, in which case the alkylene bond may contain 1 oxygen atom, sulfur atom or nitrogen atom], [R 11 and R 12 may Bonding to each other to form a C 2 to C 6 alkylene bond, in which case the alkylene bond may contain 1 oxygen atom, sulfur atom or nitrogen atom] or [R 12 and R 14 may be bonded to each other to form C 2 to C 6 alkylene bond, in which case the alkylene bond may contain 1 oxygen atom, sulfur atom or nitrogen atom] etc. by the alkylene bond and adjacent to the alkylene bond Specific examples of the heterocyclic ring formed by the atoms include, for example, Aziridine, Azetidine, Pyrrolidine,
Figure 108129126-A0202-12-0047-164
Oxazolidine,
Figure 108129126-A0202-12-0047-130
Oxazoline, iso
Figure 108129126-A0202-12-0047-165
Oxazoline, Thiazolidine, Imidazolidine, Piperidine, Morpholine, Thiomorpholine, Thiomorpholine-1-oxide, Thiomorpholine -1,1-dioxide, piper
Figure 108129126-A0202-12-0047-132
(Piperazine), hexamethyleneimine (Homopiperidine) or heptamethyleneimine and other groups.

於本發明中，[R14及R15可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子]等標示之藉由該伸烷基鍵及與該伸烷基鍵相鄰接之原子所形成之雜環的具體例，可列舉例如：4,5-二氫異

Figure 108129126-A0202-12-0048-133
唑等基。 In the present invention, [R 14 and R 15 may be bonded to each other to form a C 2 to C 6 alkylene bond, in which case the alkylene bond may contain 1 oxygen atom, sulfur atom or nitrogen atom] etc. Specific examples of the heterocyclic ring formed by the alkylene bond and the atoms adjacent to the alkylene bond include, for example, 4,5-dihydroiso
Figure 108129126-A0202-12-0048-133
Azole and other groups.

於本發明中，[C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代]等標示，係與構成伸烷基鍵之碳原子鍵結的氫原子藉由鹵素原子或C1至C6烷基取代而成之C2至C6伸烷基鍵，進行取代之鹵素原子或C1至C6烷基的數目在單取代之情形中，係表示鹵素原子或C1至C6烷基中之任一者作為取代基進行取代，在多取代之情形中，係表示2個以上的鹵素原子或C1至C6烷基中之任一者作為取代基進行取代。再者，於C2至C6伸烷基鍵上進行多取代時(亦即，存在2個以上取代基時)，各取代基可彼此相同或彼此相異。 In the present invention, [C 2 to C 6 alkylene bond can be mono- or multi-substituted by halogen atom or C 1 to C 6 alkyl group], etc., it is bonded to the carbon atom constituting the alkylene bond the number of hydrogen atoms by a halogen atom or a C 1 to C 6 alkyl substituted with of C 2 to C 6 alkylene bond, a substitution of a halogen atom or a C 1 to C 6 alkyl mono-substituted in the case of , Means a halogen atom or any one of C 1 to C 6 alkyl groups is substituted as a substituent, in the case of multiple substitution, it means two or more halogen atoms or any one of C 1 to C 6 alkyl groups One is substituted as a substituent. Furthermore, when multiple substitution is performed on the C 2 to C 6 alkylene bond (that is, when there are more than two substituents), each substituent may be the same as or different from each other.

於本發明中所謂農業上所容許之鹽以及鹽，在通式[I]所表示之本發明之化合物中，於該結構中存在有羥基、羧基或胺基等時，意指此等與金屬或有機鹼之鹽或是與無機酸或有機酸之鹽，金屬可列舉出鈉或鉀等鹼金屬或是鎂或鈣等鹼土類金屬，有機鹼可列舉出三乙胺或二異丙胺等，無機酸可列舉出鹽酸、氫溴酸或硫酸等，再者，有機酸可列舉出甲酸、乙酸、甲烷磺酸、4-甲苯磺酸或三氟甲烷磺酸等。 In the present invention, the so-called agriculturally acceptable salts and salts, in the compound of the present invention represented by the general formula [I], when there is a hydroxyl group, a carboxyl group, an amine group, etc. in the structure, it means that these and the metal Or salts of organic bases or salts with inorganic acids or organic acids, metals include alkali metals such as sodium or potassium, or alkaline earth metals such as magnesium or calcium, and organic bases include triethylamine or diisopropylamine, Examples of inorganic acids include hydrochloric acid, hydrobromic acid, sulfuric acid, and the like, and examples of organic acids include formic acid, acetic acid, methanesulfonic acid, 4-toluenesulfonic acid, and trifluoromethanesulfonic acid.

接著於表1至表25中顯示通式[I]所表示之本發明之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物所包含之化合物的代表性化合物例，於表26至表55中顯示通式[II]所表示之本發明之3-(1H-1,2,4-***-1-基)苯甲酸衍生物所包含之化合物的代表性化合物例，於表56至表58中顯示通式 [III]所表示之本發明之1-苯基-1H-1,2,4-***衍生物所包含之化合物的代表性化合物例。然而，本發明之衍生物所包含之化合物並不限定於此等。再者，於後述記載中參考表中的化合物號碼。 Next, the representative of the compound contained in the 3-(1H-1,2,4-triazol-1-yl) benzamide derivative of the present invention represented by the general formula [I] is shown in Tables 1 to 25 Examples of inert compounds are shown in Tables 26 to 55 in the compounds contained in the 3-(1H-1,2,4-triazol-1-yl)benzoic acid derivative of the present invention represented by the general formula [II] Representative compound examples with general formulas shown in Tables 56 to 58 [III] A representative compound example of the compound contained in the 1-phenyl-1H-1,2,4-triazole derivative of the present invention represented by [III]. However, the compounds included in the derivatives of the present invention are not limited to these. In addition, the compound numbers in the table are referred to in the description below.

此外，本發明之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物、3-(1H-1,2,4-***-1-基)苯甲酸衍生物或1-苯基-1H-1,2,4-***衍生物所包含之化合物中，根據取代基種類而存在有E-體及Z-體的幾何異構物之情形，惟，本發明係包含此等E-體、Z-體或是以任意比率含有E-體及Z-體之混合物。再者，本發明所包含之化合物存在有起因於1個或2個以上不對稱碳原子及不對稱硫原子的存在所致之光學異構物，惟，本發明係包含全部的光學活性體、外消旋體或非鏡像異構物。 In addition, the 3-(1H-1,2,4-triazol-1-yl)benzamide derivative and 3-(1H-1,2,4-triazol-1-yl)benzoic acid of the present invention The derivative or the compound included in the 1-phenyl-1H-1,2,4-triazole derivative may have geometric isomers of E-form and Z-form depending on the type of substituent, but, The present invention includes these E-body, Z-body or a mixture containing the E-body and Z-body in any ratio. Furthermore, the compounds included in the present invention have optical isomers due to the presence of one or more asymmetric carbon atoms and asymmetric sulfur atoms. However, the present invention includes all optically active substances, Racemate or diastereomer.

本說明書中之表中的下列標示，例如為下述所示般分別表示所對應之基。 The following symbols in the tables in this specification are, for example, the corresponding bases as shown below.

Me：甲基、 Me: methyl,

Et：乙基、 Et: ethyl,

n-Pr：正丙基、 n-Pr: n-propyl,

i-Pr：異丙基、 i-Pr: isopropyl,

c-Pr：環丙基、 c-Pr: cyclopropyl,

n-Bu：正丁基、 n-Bu: n-butyl,

s-Bu：第二丁基、 s-Bu: second butyl,

i-Bu：異丁基、 i-Bu: isobutyl,

t-Bu：第三丁基、 t-Bu: tertiary butyl,

c-Bu：環丁基、 c-Bu: cyclobutyl,

n-Pen：正戊基、 n-Pen: n-pentyl,

c-Pen：環戊基、 c-Pen: cyclopentyl,

n-Hex：正己基、 n-Hex: n-hexyl,

c-Hex：環己基、 c-Hex: cyclohexyl,

c-Pr(2,2-F2)：2,2-二氟環丙基 c-Pr(2,2-F 2 ): 2,2-difluorocyclopropyl

Ph：苯基、 Ph: phenyl,

3-Py：3-吡啶基 3-Py: 3-pyridyl

Ph(4-CF3)：4-三氟甲基苯基、 Ph(4-CF 3 ): 4-trifluoromethylphenyl,

Ph(3-OMe,4-OH)：4-羥基-3-甲氧基苯基、 Ph(3-OMe,4-OH): 4-hydroxy-3-methoxyphenyl,

[表1]

Figure 108129126-A0202-12-0051-216
[Table 1]
Figure 108129126-A0202-12-0051-216

[表2]

Figure 108129126-A0202-12-0052-217
[Table 2]
Figure 108129126-A0202-12-0052-217

[表3]

Figure 108129126-A0202-12-0053-218
[table 3]
Figure 108129126-A0202-12-0053-218

[表4]

Figure 108129126-A0202-12-0054-219
[Table 4]
Figure 108129126-A0202-12-0054-219

[表5]

Figure 108129126-A0202-12-0055-220
[table 5]
Figure 108129126-A0202-12-0055-220

[表6]

Figure 108129126-A0202-12-0056-221
[Table 6]
Figure 108129126-A0202-12-0056-221

[表7]

Figure 108129126-A0202-12-0057-222
[Table 7]
Figure 108129126-A0202-12-0057-222

[表8]

Figure 108129126-A0202-12-0058-223
[Table 8]
Figure 108129126-A0202-12-0058-223

[表9]

Figure 108129126-A0202-12-0059-224
[Table 9]
Figure 108129126-A0202-12-0059-224

[表10]

Figure 108129126-A0202-12-0060-225
[Table 10]
Figure 108129126-A0202-12-0060-225

[表11]

Figure 108129126-A0202-12-0061-226
[Table 11]
Figure 108129126-A0202-12-0061-226

[表12]

Figure 108129126-A0202-12-0062-227
[Table 12]
Figure 108129126-A0202-12-0062-227

[表13]

Figure 108129126-A0202-12-0063-228
[Table 13]
Figure 108129126-A0202-12-0063-228

[表14]

Figure 108129126-A0202-12-0064-229
[Table 14]
Figure 108129126-A0202-12-0064-229

[表15]

Figure 108129126-A0202-12-0065-230
[Table 15]
Figure 108129126-A0202-12-0065-230

[表16]

Figure 108129126-A0202-12-0066-231
[Table 16]
Figure 108129126-A0202-12-0066-231

[表17]

Figure 108129126-A0202-12-0067-232
[Table 17]
Figure 108129126-A0202-12-0067-232

[表18]

Figure 108129126-A0202-12-0068-233
[Table 18]
Figure 108129126-A0202-12-0068-233

[表19]

Figure 108129126-A0202-12-0069-234
[Table 19]
Figure 108129126-A0202-12-0069-234

[表20]

Figure 108129126-A0202-12-0070-235
[Table 20]
Figure 108129126-A0202-12-0070-235

[表21]

Figure 108129126-A0202-12-0071-236
[Table 21]
Figure 108129126-A0202-12-0071-236

[表22]

Figure 108129126-A0202-12-0072-237
[Table 22]
Figure 108129126-A0202-12-0072-237

[表23]

Figure 108129126-A0202-12-0073-238
[Table 23]
Figure 108129126-A0202-12-0073-238

[表24]

Figure 108129126-A0202-12-0074-239
[Table 24]
Figure 108129126-A0202-12-0074-239

[表25]

Figure 108129126-A0202-12-0075-240
[Table 25]
Figure 108129126-A0202-12-0075-240

[表26]

Figure 108129126-A0202-12-0076-241
[Table 26]
Figure 108129126-A0202-12-0076-241

[表27]

Figure 108129126-A0202-12-0077-242
[Table 27]
Figure 108129126-A0202-12-0077-242

[表28]

Figure 108129126-A0202-12-0078-243
[Table 28]
Figure 108129126-A0202-12-0078-243

[表29]

Figure 108129126-A0202-12-0079-244
[Table 29]
Figure 108129126-A0202-12-0079-244

[表30]

Figure 108129126-A0202-12-0080-245
[Table 30]
Figure 108129126-A0202-12-0080-245

[表31]

Figure 108129126-A0202-12-0081-246
[Table 31]
Figure 108129126-A0202-12-0081-246

[表32]

Figure 108129126-A0202-12-0082-247
[Table 32]
Figure 108129126-A0202-12-0082-247

[表33]

Figure 108129126-A0202-12-0083-248
[Table 33]
Figure 108129126-A0202-12-0083-248

[表34]

Figure 108129126-A0202-12-0084-249
[Table 34]
Figure 108129126-A0202-12-0084-249

[表35]

Figure 108129126-A0202-12-0085-250
[Table 35]
Figure 108129126-A0202-12-0085-250

[表36]

Figure 108129126-A0202-12-0086-251
[Table 36]
Figure 108129126-A0202-12-0086-251

[表37]

Figure 108129126-A0202-12-0087-252
[Table 37]
Figure 108129126-A0202-12-0087-252

[表38]

Figure 108129126-A0202-12-0088-253
[Table 38]
Figure 108129126-A0202-12-0088-253

[表39]

Figure 108129126-A0202-12-0089-254
[Table 39]
Figure 108129126-A0202-12-0089-254

[表40]

Figure 108129126-A0202-12-0090-255
[Table 40]
Figure 108129126-A0202-12-0090-255

[表41]

Figure 108129126-A0202-12-0091-256
[Table 41]
Figure 108129126-A0202-12-0091-256

[表42]

Figure 108129126-A0202-12-0092-257
[Table 42]
Figure 108129126-A0202-12-0092-257

[表43]

Figure 108129126-A0202-12-0093-258
[Table 43]
Figure 108129126-A0202-12-0093-258

[表44]

Figure 108129126-A0202-12-0094-259
[Table 44]
Figure 108129126-A0202-12-0094-259

[表45]

Figure 108129126-A0202-12-0095-260
[Table 45]
Figure 108129126-A0202-12-0095-260

[表46]

Figure 108129126-A0202-12-0096-261
[Table 46]
Figure 108129126-A0202-12-0096-261

[表47]

Figure 108129126-A0202-12-0097-262
[Table 47]
Figure 108129126-A0202-12-0097-262

[表48]

Figure 108129126-A0202-12-0098-263
[Table 48]
Figure 108129126-A0202-12-0098-263

[表49]

Figure 108129126-A0202-12-0099-264
[Table 49]
Figure 108129126-A0202-12-0099-264

[表50]

Figure 108129126-A0202-12-0100-265
[Table 50]
Figure 108129126-A0202-12-0100-265

[表51]

Figure 108129126-A0202-12-0101-266
[Table 51]
Figure 108129126-A0202-12-0101-266

[表52]

Figure 108129126-A0202-12-0102-267
[Table 52]
Figure 108129126-A0202-12-0102-267

[表53]

Figure 108129126-A0202-12-0103-268
[Table 53]
Figure 108129126-A0202-12-0103-268

[表54]

Figure 108129126-A0202-12-0104-269
[Table 54]
Figure 108129126-A0202-12-0104-269

[表55]

Figure 108129126-A0202-12-0105-270
[Table 55]
Figure 108129126-A0202-12-0105-270

[表56]

Figure 108129126-A0202-12-0106-271
[Table 56]
Figure 108129126-A0202-12-0106-271

[表57]

Figure 108129126-A0202-12-0107-272
[Table 57]
Figure 108129126-A0202-12-0107-272

[表58]

Figure 108129126-A0202-12-0108-273
[Table 58]
Figure 108129126-A0202-12-0108-273

另一方面，通式[I]所表示之本發明之化合物可依循下述所示之製造法來製造，但並不限定於此等方法。此外，以下例如將「通式[I-1]所表示之化合物」及「化合物[I-1]」設為同義。 On the other hand, the compound of the present invention represented by the general formula [I] can be produced according to the production method shown below, but it is not limited to these methods. In the following, for example, "a compound represented by the general formula [I-1]" and "compound [I-1]" are synonymous.

〈製造方法1〉 <Manufacturing method 1>

本發明之化合物中，通式[I-1]所表示之化合物例如可使用通式[III-1]所表示之化合物並依循由下述所例示之反應式所組成之方法來製造。 Among the compounds of the present invention, the compound represented by the general formula [I-1] can be produced, for example, using the compound represented by the general formula [III-1] and following the method composed of the reaction formula exemplified below.

Figure 108129126-A0202-12-0109-274
Figure 108129126-A0202-12-0109-274

(式中，R1、R2、R3、R4、R5、R6、K及n表示與前述相同意義，Ra表示氫原子、鹵素原子、氰基、-C(=O)K或-C(=O)NR1R2，L1表示鹵素原子，L2表示C1至C6烷氧基或C1至C6烷基硫基，Rb表示C1至C6烷基等) (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , K and n have the same meaning as described above, R a represents a hydrogen atom, a halogen atom, a cyano group, -C(=O)K Or -C(=O)NR 1 R 2 , L 1 represents a halogen atom, L 2 represents C 1 to C 6 alkoxy or C 1 to C 6 alkylthio, R b represents C 1 to C 6 alkyl Wait)

(步驟1-1) (Step 1-1)

亦即，通式[I-1]所表示之化合物可藉由在適當之鹼的存在下，於適當的溶劑中使通式[III-1]所表示之化合物與化合物[IV-1]或化合物[IV-2]進行反應而製造。 That is, the compound represented by the general formula [I-1] can be prepared by using the compound represented by the general formula [III-1] and the compound [IV-1] in the presence of an appropriate base in an appropriate solvent or The compound [IV-2] is produced by reacting.

相對於化合物[III-1]1莫耳，本步驟中所使用之化合物[IV-1]或化合物[IV-2]的使用量可適當地選自1莫耳至相當於溶劑量的範圍，較佳為1.0至2.0莫耳。 The use amount of the compound [IV-1] or the compound [IV-2] used in this step can be appropriately selected from the range of 1 mole to the amount of the solvent relative to the compound [III-1] 1 mole. It is preferably 1.0 to 2.0 moles.

本步驟中所能夠使用之鹼可列舉例如：氫氧化鈉、氫氧化鉀、氫氧化鋰等鹼金屬的氫氧化物類；氫氧化鈣、氫氧化鎂等鹼土類金屬的氫氧化物類；碳酸鈉、碳酸鉀等鹼金屬的碳酸鹽類；碳酸氫鈉、碳酸氫鉀等鹼金屬的重碳酸鹽類等無機鹼類；氫化鈉、氫化鉀等金屬氫化物類；甲氧化鈉、乙氧化鈉、第三丁氧化鉀等醇的金屬鹽類；或是三乙胺、N,N-二甲基苯胺、吡啶、4-N,N-二甲基胺基吡啶、1,8-二氮雜雙環[5,4,0]-7-十一烯等有機鹼類等。此外，相對於化合物[III-1]1莫耳，鹼的使用量可適當地選自1至5莫耳的範圍，較佳為1.0至3.0莫耳。 Examples of the base that can be used in this step include: hydroxides of alkali metals such as sodium hydroxide, potassium hydroxide, and lithium hydroxide; hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide; and carbonic acid Carbonates of alkali metals such as sodium and potassium carbonate; inorganic bases such as bicarbonates of alkali metals such as sodium bicarbonate and potassium bicarbonate; metal hydrides such as sodium hydride and potassium hydride; sodium methoxide and sodium ethoxide , Metal salts of alcohols such as potassium tributoxide, or triethylamine, N,N-dimethylaniline, pyridine, 4-N,N-dimethylaminopyridine, 1,8-diaza Bicyclic [5,4,0]-7-undecene and other organic bases. In addition, the amount of the base used can be appropriately selected from the range of 1 to 5 moles relative to 1 mole of compound [III-1], preferably 1.0 to 3.0 moles.

本步驟中所能夠使用之溶劑可列舉例如：二***、環戊基甲醚、四氫呋喃、2-甲基四氫呋喃、1,4-二

Figure 108129126-A0202-12-0110-150
烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇等醇類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；乙酸乙酯等酯類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；吡啶、甲吡啶(Picoline)等吡啶類或此等混合溶劑等。此外，相對於化合物[III-1]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至10公升。 Examples of solvents that can be used in this step include: diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-bis
Figure 108129126-A0202-12-0110-150
Ethers such as alkane; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrole Aprotic polar solvents such as pyridone, dimethyl sulfoxide, cis-butane, 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol; dichloromethane, Halogenated hydrocarbons such as chloroform and 1,2-dichloroethane; esters such as ethyl acetate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; pyridines such as pyridine and picoline Or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 100 liters relative to 1 mole of the compound [III-1], preferably 0.3 to 10 liters.

本步驟之反應溫度可選自從0℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於0℃至150℃的範圍內進行。 The reaction temperature in this step can be selected from any temperature range from 0°C to the reflux temperature in the reaction system, and preferably can be performed in the range of 0°C to 150°C.

本步驟之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為15分鐘至24小時。 Although the reaction time in this step varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 15 minutes to 24 hours.

反應結束後，將反應混合物注加於水中並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[I-1]。單離出之化合物[I-1]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water and extracted with an organic solvent, followed by concentration and other operations, whereby the compound [I-1] can be isolated. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc. as required.

(步驟1-2) (Step 1-2)

再者，通式[I-1]所表示之化合物可藉由使通式[III-1]所表示之化合物與胺基化劑進行反應而製造通式[III-2]所表示之化合物，然後在適當之鹼的存在下或不存在下、適當之酸觸媒的存在下或不存在下，於適當的溶劑中使此化合物[III-2]與化合物[IV-3]或化合物[IV-4]進行反應而製造。 Furthermore, the compound represented by general formula [I-1] can produce the compound represented by general formula [III-2] by reacting the compound represented by general formula [III-1] with an aminating agent, Then, in the presence or absence of an appropriate base, the presence or absence of an appropriate acid catalyst, the compound [III-2] and compound [IV-3] or compound [IV -4] Manufactured by reacting.

本步驟中能夠使用之胺基化劑可列舉例如：氨、氨水等。此外，相對於化合物[III-1]1莫耳，胺基化劑的使用量可適當地選自1至30莫耳的範圍，較佳為1.0至25.0莫耳。 Examples of the aminating agent that can be used in this step include ammonia and ammonia water. In addition, the amount of the aminating agent used can be appropriately selected from the range of 1 to 30 moles relative to 1 mole of compound [III-1], preferably 1.0 to 25.0 moles.

本步驟中能夠使用之溶劑可列舉例如：二***、環戊基甲醚、四氫呋喃、2-甲基四氫呋喃、1,4-二

Figure 108129126-A0202-12-0111-134
烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；乙腈、丙腈等腈類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇等醇類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；乙酸乙酯等酯類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；吡啶、甲吡啶等吡啶類或此等混合溶劑等。此外，相對於化合物[III-1]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至10公升。 Examples of solvents that can be used in this step include: diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-bis
Figure 108129126-A0202-12-0111-134
Ethers such as alkanes; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile and propionitrile; N,N-dimethylformamide, N,N-dimethylacetamide, Aprotic polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; methanol, ethanol, 2-propanol Alcohols; dichloromethane, chloroform, 1,2-dichloroethane and other halogenated hydrocarbons; ethyl acetate and other esters; pentane, hexane, cyclohexane, heptane and other aliphatic hydrocarbons; pyridine, Pyridines such as picoline or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 100 liters relative to 1 mole of the compound [III-1], preferably 0.3 to 10 liters.

本步驟之反應溫度可選自從-30℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於-10℃至100℃的範圍內進行。 The reaction temperature in this step can be selected from any temperature range from -30°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of -10°C to 100°C.

本步驟之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為15分鐘至24小時。 Although the reaction time in this step varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 15 minutes to 24 hours.

反應結束後將反應混合物注加於水中並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[III-2]。單離出之化合物[III-2]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water and extracted with an organic solvent, followed by concentration, etc., whereby the compound [III-2] can be isolated. The isolated compound [III-2] can be further purified by column chromatography, recrystallization, etc. as required.

(步驟1-3) (Steps 1-3)

相對於化合物[III-2]1莫耳，本步驟中使用之化合物[IV-3]或化合物[IV-4]的使用量可適當地選自從1莫耳至相當於溶劑量的範圍，較佳為1.0至10.0莫耳。惟，化合物[IV-4]亦可作為上述溶劑使用。 The amount of compound [IV-3] or compound [IV-4] used in this step can be appropriately selected from the range from 1 mole to the equivalent amount of solvent relative to 1 mole of compound [III-2]. Preferably, it is 1.0 to 10.0 mol. However, the compound [IV-4] can also be used as the above solvent.

於本步驟中使用酸觸媒時，能夠使用之酸觸媒可列舉例如：甲烷磺酸或對甲苯磺酸等磺酸類；鹽酸、氫溴酸或硫酸等無機酸類；乙酸或三氟乙酸等羧酸類等。此外，相對於化合物[III-2]1莫耳，酸觸媒的使用量可適當地選自0.01莫耳至10莫耳的範圍，較佳為0.05至1.0莫耳。 When an acid catalyst is used in this step, examples of acid catalysts that can be used include: methanesulfonic acid or p-toluenesulfonic acid; sulfonic acids such as hydrochloric acid, hydrobromic acid, or sulfuric acid; carboxylic acids such as acetic acid or trifluoroacetic acid Acids, etc. In addition, the amount of the acid catalyst used can be appropriately selected from the range of 0.01 mol to 10 mol, preferably 0.05 to 1.0 mol relative to 1 mol of the compound [III-2].

於本步驟中使用鹼時，能夠使用之鹼可列舉例如：氫氧化鈉、氫氧化鉀、氫氧化鋰等鹼金屬的氫氧化物類；氫氧化鈣、氫氧化鎂等鹼土類金屬的氫氧化物類；碳酸鈉、碳酸鉀等鹼金屬的碳酸鹽類；碳酸氫鈉、碳酸氫鉀等鹼金屬的重碳酸鹽類等無機鹼類；氫化鈉、氫化鉀等金屬氫化物類；甲氧化鈉、乙氧化鈉、第三丁氧化鉀等醇的金屬鹽類；或三乙胺、N,N-二甲基苯胺、吡啶、4-N,N-二甲基胺基吡啶、1,8-二氮雜雙環[5,4,0]-7-十一 烯等有機鹼類等。此外，相對於化合物[III-2]1莫耳，鹼的使用量可適當地選自從1莫耳至相當於溶劑量的範圍，較佳為1.0至1.5莫耳。 When an alkali is used in this step, the alkali that can be used includes, for example, hydroxides of alkali metals such as sodium hydroxide, potassium hydroxide, and lithium hydroxide; hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide Species; carbonates of alkali metals such as sodium carbonate and potassium carbonate; inorganic bases such as bicarbonates of alkali metals such as sodium bicarbonate and potassium bicarbonate; metal hydrides such as sodium hydride and potassium hydride; sodium methoxide , Sodium ethoxide, potassium tributoxide and other metal salts of alcohol; or triethylamine, N,N-dimethylaniline, pyridine, 4-N,N-dimethylaminopyridine, 1,8- Diazabicyclo[5,4,0]-7-eleven Organic bases such as alkenes. In addition, the amount of the base used can be appropriately selected from the range of 1 mole to the equivalent of the solvent relative to 1 mole of the compound [III-2], preferably 1.0 to 1.5 moles.

本步驟中能夠使用之溶劑可列舉例如：二***、環戊基甲醚、四氫呋喃、2-甲基四氫呋喃、1,4-二

Figure 108129126-A0202-12-0113-163
烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；乙腈、丙腈等腈類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇等醇類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；乙酸乙酯等酯類；戊烷、己烷、環己烷及庚烷等脂肪族烴類；吡啶、甲吡啶等吡啶類；正甲酸三甲酯、正甲酸三乙酯、正乙酸三甲酯、正乙酸三乙酯等原酯類或此等混合溶劑等。相對於化合物[III-2]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至10公升。 Examples of solvents that can be used in this step include: diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-bis
Figure 108129126-A0202-12-0113-163
Ethers such as alkanes; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile and propionitrile; N,N-dimethylformamide, N,N-dimethylacetamide, Aprotic polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; methanol, ethanol, 2-propanol Alcohols; dichloromethane, chloroform, 1,2-dichloroethane and other halogenated hydrocarbons; ethyl acetate and other esters; pentane, hexane, cyclohexane and heptane and other aliphatic hydrocarbons; pyridine, Pyridines such as picoline; trimethyl orthoformate, triethyl orthoformate, trimethyl orthoacetate, triethyl orthoacetate and other mixed solvents. The use amount of the solvent is 0.1 to 100 liters, preferably 0.3 to 10 liters relative to 1 mole of compound [III-2].

本步驟之反應溫度可選自從-30℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於-10℃至100℃的範圍內進行。 The reaction temperature in this step can be selected from any temperature range from -30°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of -10°C to 100°C.

本步驟之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為15分鐘至24小時。 Although the reaction time in this step varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 15 minutes to 24 hours.

反應結束後將反應混合物注加於水中並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[I-1]。單離出之化合物[I-1]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water and extracted with an organic solvent, followed by concentration and other operations, whereby the compound [I-1] can be isolated. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc. as required.

〈製造方法2〉 <Manufacturing method 2>

本發明之化合物中，通式[I-1]所表示之化合物及通式[I-2]所表示之化合物，係例如可使用通式[III-3]所表示之化合物並依循由下述所例示之反應式所組成之方法來製造。 Among the compounds of the present invention, the compound represented by the general formula [I-1] and the compound represented by the general formula [I-2] are, for example, compounds represented by the general formula [III-3] and can be used in accordance with the following Manufactured by the method composed of the illustrated reaction formula.

Figure 108129126-A0202-12-0114-275
Figure 108129126-A0202-12-0114-275

(式中，R3、R4、R5、R6、Ra及n表示與前述相同意義，L3表示鹵素原子、C1至C6烷氧基、C1至C6鹵烷氧基、苯基氧基、C1至C6烷基硫基或C1至C6鹵烷基硫基) (Wherein, R 3, R 4, R 5, R 6, R a and n represent the same meaning, L 3 represents a halogen atom, C 1 to C 6 alkoxy group, C 1 to C 6 haloalkoxy , Phenyloxy, C 1 to C 6 alkylthio or C 1 to C 6 haloalkylthio)

(步驟2-1) (Step 2-1)

亦即，通式[I-1]所表示之化合物可藉由在適當之酸的存在下或不存在下，於適當的溶劑中使從化合物[IV-5]與酸鹵化物及酸酐等所衍生之化合物[IV-6]與通式[III-3]所表示之化合物進行反應而製造。 That is, the compound represented by the general formula [I-1] can be obtained from the compound [IV-5] and acid halide and acid anhydride in the presence or absence of an appropriate acid in an appropriate solvent. The derivative compound [IV-6] is produced by reacting the compound represented by the general formula [III-3].

相對於化合物[III-3]1莫耳，本步驟中所使用之化合物[IV-6]的使用量可適當地選自1至5莫耳的範圍，較佳為1.0至2.5莫耳。 The use amount of the compound [IV-6] used in this step can be appropriately selected from the range of 1 to 5 moles, preferably 1.0 to 2.5 moles relative to 1 mole of compound [III-3].

於本步驟中使用酸時，能夠使用之酸，可列舉例如：甲烷磺酸或對甲苯磺酸等磺酸類；鹽酸、氫溴酸或硫酸等無機酸類；乙酸或三氟乙酸等羧 酸類等。此外，相對於化合物[III-3]1莫耳，酸的使用量可適當地選自0.001至10莫耳的範圍，較佳為0.001至3.0莫耳。 When the acid is used in this step, the acids that can be used include, for example, sulfonic acids such as methanesulfonic acid or p-toluenesulfonic acid; inorganic acids such as hydrochloric acid, hydrobromic acid or sulfuric acid; carboxylic acids such as acetic acid or trifluoroacetic acid Acids, etc. In addition, the amount of acid used can be appropriately selected from the range of 0.001 to 10 mol, preferably 0.001 to 3.0 mol, relative to 1 mol of compound [III-3].

本步驟中能夠使用之溶劑可列舉例如：二***、環戊基甲醚、四氫呋喃、2-甲基四氫呋喃、1,4-二

Figure 108129126-A0202-12-0115-151
烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；乙腈、丙腈等腈類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇等醇類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；水或此等混合溶劑等。此外，相對於化合物[III-3]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至10公升。 Examples of solvents that can be used in this step include: diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-bis
Figure 108129126-A0202-12-0115-151
Ethers such as alkanes; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile and propionitrile; N,N-dimethylformamide, N,N-dimethylacetamide, Aprotic polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; methanol, ethanol, 2-propanol Alcohols; dichloromethane, chloroform, 1,2-dichloroethane and other halogenated hydrocarbons; pentane, hexane, cyclohexane, heptane and other aliphatic hydrocarbons; water or these mixed solvents, etc. In addition, the amount of the solvent used is 0.1 to 100 liters, preferably 0.3 to 10 liters relative to 1 mole of the compound [III-3].

本步驟之反應溫度可選自從-30℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於-10℃至100℃的範圍內進行。 The reaction temperature in this step can be selected from any temperature range from -30°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of -10°C to 100°C.

本步驟之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為10分鐘至20小時。 Although the reaction time in this step varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 10 minutes to 20 hours.

反應結束後將反應混合物注加於水中並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[I-1]。單離出之化合物[I-1]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water and extracted with an organic solvent, followed by concentration and other operations, whereby the compound [I-1] can be isolated. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc. as required.

(步驟2-2) (Step 2-2)

再者，通式[I-2]所表示之化合物可在適當的溶劑中使從化合物[IV-7]、二硫化碳及鹵化烷等所衍生之化合物[IV-8]與通式[III-3]所表示之化合物進行反應而製造。 In addition, the compound represented by the general formula [I-2] can be obtained by compound [IV-8] and general formula [III-3 derived from the compound [IV-7], carbon disulfide, alkyl halide, etc. in an appropriate solvent ] The compound represented by the reaction is produced.

相對於化合物[III-3]1莫耳，本步驟中所使用之化合物[IV-8]的使用量可適當地選自1至10莫耳的範圍，較佳為1.0至1.5莫耳。 The amount of the compound [IV-8] used in this step can be appropriately selected from the range of 1 to 10 moles relative to 1 mole of compound [III-3], preferably 1.0 to 1.5 moles.

本步驟中能夠使用之溶劑可列舉例如：與前述步驟3中所說明者為同樣之溶劑。相對於化合物[III-3]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至10公升。 Examples of the solvent that can be used in this step include the same solvents as those described in step 3 above. The use amount of the solvent is 0.1 to 100 liters, preferably 0.3 to 10 liters relative to 1 mole of compound [III-3].

本步驟之反應溫度可選自從-30℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於-10℃至100℃的範圍內進行。 The reaction temperature in this step can be selected from any temperature range from -30°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of -10°C to 100°C.

本步驟之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為10分鐘至20小時。 Although the reaction time in this step varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 10 minutes to 20 hours.

反應結束後將反應混合物注加於水中並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[I-2]。或者是，亦可藉由從反應混合物中將溶劑濃縮而單離出化合物[I-2]。單離出之化合物[I-2]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water and extracted with an organic solvent, followed by concentration and other operations, whereby the compound [I-2] can be isolated. Alternatively, the compound [I-2] can also be isolated by concentrating the solvent from the reaction mixture. The isolated compound [I-2] can be further purified by column chromatography, recrystallization, etc. as required.

〈製造方法3〉 <Manufacturing method 3>

本發明之化合物中，通式[I-4]所表示之化合物、通式[I-5]所表示之化合物及通式[I-6]所表示之化合物，例如，可使用通式[I-3]所表示之化合物並依循由下述所例示之反應式所組成之方法來製造。 Among the compounds of the present invention, the compound represented by the general formula [I-4], the compound represented by the general formula [I-5] and the compound represented by the general formula [I-6], for example, the general formula [I -3] The compound represented is produced according to the method composed of the reaction formula exemplified below.

Figure 108129126-A0202-12-0117-276
Figure 108129126-A0202-12-0117-276

(式中，R3、R4、R6、R13、Ra、Z、p1及n表示與前述相同意義，M表示鹼金屬或鹼土類金屬，較佳的鹼金屬可列舉出鈉或鉀，R5a表示C1至C6烷基、C1至C6鹵烷基、經R13任意地取代之C1至C6烷基、經R13任意地取代之C1至C6鹵烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C3至C6環烷基、C3至C6鹵環烷基、無取代或經(Z)p1取代之苯基、芳香族雜環或飽和雜環) (Wherein, R 3, R 4, R 6, R 13, R a, Z, p 1 , and n represents the same meaning, M is an alkali metal or an alkaline earth metal, preferably alkali metals include sodium or K, R 5a represents a C 1 to C 6 alkyl, a C 1 to C 6 haloalkyl, optionally substituted with R of C 13 1 to C 6 alkyl, optionally substituted with R of C 6 to C 13 1 halo Alkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, unsubstituted or (Phenyl, aromatic heterocycle or saturated heterocycle substituted with (Z)p 1 )

亦即，通式[I-4]所表示之化合物、通式[I-5]所表示之化合物及通式[I-6]所表示之化合物，可於適當的溶劑中依據Organic Syntheses,Coll.Vol.3,p.185(1955)所記載的方法(例如，藉由使用鹽酸及硫酸等無機酸與亞硝酸鹽或亞硝酸烷酯之方法)，將化合物[I-3]形成為重氮鹽後，在化合物[IV-9]所表示之硫醇的鹽、化合物[IV-10]所表示之二硫化物類或鹵化銅的存在下或不存在下，於適當的溶劑中進行反應而分別製造。 That is, the compound represented by the general formula [I-4], the compound represented by the general formula [I-5] and the compound represented by the general formula [I-6] can be used in an appropriate solvent according to Organic Syntheses, Coll .Vol.3, p.185 (1955) method (for example, by using hydrochloric acid and sulfuric acid and other inorganic acids and nitrite or alkyl nitrite method), the compound [I-3] is formed into diazo After the salt, the reaction is carried out in an appropriate solvent in the presence or absence of the thiol salt represented by compound [IV-9], the disulfide represented by compound [IV-10], or copper halide. Made separately.

(步驟3-1) (Step 3-1)

相對於化合物[I-3]1莫耳，本步驟中所使用之化合物[IV-9]或化合物[IV-10]的使用量可適當地選自1至5莫耳的範圍，較佳為1.0至2.0莫耳。 The amount of the compound [IV-9] or compound [IV-10] used in this step can be appropriately selected from the range of 1 to 5 moles relative to 1 mole of compound [I-3], preferably 1.0 to 2.0 moles.

本步驟中能夠使用之溶劑可列舉例如：二***、環戊基甲醚、四氫呋喃、2-甲基四氫呋喃、1,4-二

Figure 108129126-A0202-12-0118-152
烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；乙腈、丙腈等腈類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮等非質子性極性溶劑類；鹽酸、硫酸等無機酸類；乙酸等羧酸類；水或此等混合溶劑等。相對於化合物[I-3]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至10公升。 Examples of solvents that can be used in this step include: diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-bis
Figure 108129126-A0202-12-0118-152
Ethers such as alkane; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane; nitriles such as acetonitrile and propionitrile; N, N -Dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2- Aprotic polar solvents such as imidazolidinone; inorganic acids such as hydrochloric acid and sulfuric acid; carboxylic acids such as acetic acid; water or these mixed solvents. The amount of the solvent used is 0.1 to 100 liters, preferably 0.3 to 10 liters relative to 1 mole of compound [I-3].

本步驟之反應溫度可選自從-70℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於-20℃至100℃的範圍內進行。 The reaction temperature in this step can be selected from any temperature range from -70°C to the reflux temperature in the reaction system, and preferably can be performed in the range of -20°C to 100°C.

本步驟之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為10分鐘至24小時。 Although the reaction time in this step varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 10 minutes to 24 hours.

反應結束後將反應混合物注加於水中並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[I-4]。單離出之化合物[I-4]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water and extracted with an organic solvent, followed by concentration and other operations, whereby the compound [I-4] can be isolated. The isolated compound [I-4] can be further purified by column chromatography, recrystallization, etc. as required.

(步驟3-2) (Step 3-2)

本步驟中能夠使用之鹵化銅可列舉例如：氯化銅(I)、溴化銅(I)、碘化銅(I)、氯化銅(II)、溴化銅(II)等。相對於化合物[I-3]1莫耳，鹵化銅的使用量可適當地選自0至5莫耳的範圍，較佳為1.0至2.5莫耳。 Examples of the copper halide that can be used in this step include copper (I), copper (I) bromide, copper (I) iodide, copper (II) chloride, and copper (II) bromide. The use amount of copper halide can be appropriately selected from the range of 0 to 5 moles relative to 1 mole of compound [I-3], preferably 1.0 to 2.5 moles.

本步驟中能夠使用之溶劑、反應溫度及反應時間係與步驟3-1相同。 The solvent, reaction temperature and reaction time that can be used in this step are the same as in step 3-1.

反應結束後將反應混合物注加於水中並中和後，濾取所析出之固體或利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[I-5]。單離出之化合物[I-5]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water and neutralized, and the precipitated solid is filtered out or extracted with an organic solvent and then concentrated to perform operations such as isolation of the compound [I-5]. The isolated compound [I-5] can be further purified by column chromatography, recrystallization, etc. as required.

(步驟3-3) (Step 3-3)

本步驟中能夠使用之溶劑可列舉例如：二***、環戊基甲醚、四氫呋喃、2-甲基四氫呋喃、1,4-二

Figure 108129126-A0202-12-0119-154
烷等醚類；乙腈、丙腈等腈類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮等非質子性極性溶劑類或此等混合溶劑等。相對於化合物[I-3]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至30公升。 Examples of solvents that can be used in this step include: diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-bis
Figure 108129126-A0202-12-0119-154
Ethers such as alkane; nitriles such as acetonitrile and propionitrile; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylmethylene Aprotic polar solvents such as ballast, ciprosone, 1,3-dimethyl-2-imidazolidinone, or these mixed solvents. The amount of the solvent used is 0.1 to 100 liters, preferably 0.3 to 30 liters relative to 1 mole of compound [I-3].

本步驟之反應溫度及反應時間係與步驟3-1相同。 The reaction temperature and reaction time in this step are the same as in step 3-1.

反應結束後將反應混合物注加於水中並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[I-6]。或者是，亦可藉由從反應混合物中將溶劑濃縮而單離出化合物[I-6]。單離出之化合物[I-6]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water and extracted with an organic solvent, followed by concentration and other operations, whereby the compound [I-6] can be isolated. Alternatively, the compound [I-6] can also be isolated by concentrating the solvent from the reaction mixture. The isolated compound [I-6] can be further purified by column chromatography, recrystallization, etc. as required.

〈製造方法4〉 <Manufacturing method 4>

本發明之化合物中，通式[I-8]所表示之化合物例如可使用通式[I-7]所表示之化合物並依循由下述所例示之反應式所組成之方法來製造。 Among the compounds of the present invention, the compound represented by the general formula [I-8] can be produced, for example, using the compound represented by the general formula [I-7] and following the method composed of the reaction formula exemplified below.

Figure 108129126-A0202-12-0119-277
Figure 108129126-A0202-12-0119-277

(式中，R3、R4、R5a、R6、Ra及n表示與前述相同意義，m表示1或2的整數) (Wherein, R 3, R 4, R 5a, R 6, R a and n represent the same meaning, m represents an integer of 1 or 2)

亦即，通式[I-8]所表示之化合物可藉由在適當之觸媒的存在下或不存在下，於適當的溶劑中使化合物[I-7]與氧化劑進行反應而製造。 That is, the compound represented by the general formula [I-8] can be produced by reacting the compound [I-7] with an oxidizing agent in an appropriate solvent in the presence or absence of an appropriate catalyst.

本反應中能夠使用之氧化劑可列舉例如：過氧化氫、間氯過氧苯甲酸、過碘酸鈉、OXONE(E.I.Du Pont公司商品名稱；過氧硫酸氫鉀含有物)、N-氯琥珀醯亞胺、N-溴琥珀醯亞胺、次氯酸第三丁酯、次氯酸鈉等。氧化劑的使用量雖與通式[I-8]所表示之化合物之硫原子的氧化數m相依，惟，相對於化合物[I-7]1莫耳，可適當地選自1至5莫耳的範圍，較佳為1.0至2.5莫耳。 Examples of oxidizing agents that can be used in this reaction include: hydrogen peroxide, m-chloroperoxybenzoic acid, sodium periodate, OXONE (trade name of EIDu Pont; potassium peroxysulfate-containing substance), N-chlorosuccinyl Imine, N-bromosuccinimide, tertiary butyl hypochlorite, sodium hypochlorite, etc. Although the amount of the oxidizing agent depends on the oxidation number m of the sulfur atom of the compound represented by the general formula [I-8], it can be appropriately selected from 1 to 5 moles relative to the compound [I-7] 1 mole. The range is preferably 1.0 to 2.5 moles.

本反應中能夠使用之觸媒可列舉例如：鎢酸鈉等。相對於化合物[I-7]1莫耳，觸媒的使用量可適當地選自0.01至1莫耳的範圍，較佳為0.01至0.1莫耳。 Examples of catalysts that can be used in this reaction include sodium tungstate. The amount of the catalyst used can be appropriately selected from the range of 0.01 to 1 mol, preferably 0.01 to 0.1 mol relative to 1 [mol] of compound [I-7].

本反應中能夠使用之溶劑可列舉例如：苯、甲苯、二甲苯、氯苯等芳香族烴類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇等醇類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；乙酸、水或此等混合溶劑等。相對於化合物[I-7]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至15公升。 Examples of solvents that can be used in this reaction include aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; N,N-dimethylformamide, N,N-dimethylacetamide, and N- Aprotic polar solvents such as methyl-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol Halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane; acetic acid, water, or mixed solvents such as these. The amount of the solvent used is 0.1 to 100 liters, preferably 0.3 to 15 liters relative to 1 mole of compound [I-7].

本反應之反應溫度通常可選自從-30℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於-10℃至100℃的範圍內進行。 The reaction temperature of this reaction can be generally selected from any temperature range from -30°C to the reflux temperature in the reaction system, and is preferably carried out in the range of -10°C to 100°C.

本反應之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為10分鐘至24小時。 Although the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 10 minutes to 24 hours.

反應結束後將反應混合物注加於水中等並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[I-8]。單離出之化合物[I-8]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water, etc., extracted with an organic solvent, and then concentrated and the like, whereby the compound [I-8] can be isolated. The single isolated compound [I-8] can be further purified by column chromatography, recrystallization, etc. as required.

〈製造方法5〉 <Manufacturing method 5>

本發明之化合物中，通式[I-11]所表示之化合物例如可使用通式[I-9]所表示之化合物並依循由下述所例示之反應式所組成之方法來製造。 Among the compounds of the present invention, the compound represented by the general formula [I-11] can be produced, for example, using the compound represented by the general formula [I-9] and following the method composed of the reaction formula exemplified below.

Figure 108129126-A0202-12-0121-278
Figure 108129126-A0202-12-0121-278

(式中，R3、R4、R6、Ra及n表示與前述相同意義，Rc表示甲基或三氟甲基) (Wherein, R 3, R 4, R 6, R a and n represent the same meaning as the foregoing, R c represents methyl or trifluoromethyl)

亦即，通式[I-11]所表示之化合物可藉由使化合物[I-9]與乙酸酐或三氟乙酸酐進行反應而製造化合物[I-10]，接著，在適當之鹼或適當之酸的存在下，於適當的溶劑中使化合物[I-10]水解而製造。 That is, the compound represented by the general formula [I-11] can be produced by reacting the compound [I-9] with acetic anhydride or trifluoroacetic anhydride to produce the compound [I-10], and then, in an appropriate base or It is produced by hydrolyzing compound [I-10] in an appropriate solvent in the presence of an appropriate acid.

相對於化合物[I-9]1莫耳，本反應中所使用之乙酸酐或三氟乙酸酐的使用量可選自從1莫耳至相當於溶劑量的範圍，較佳為1.0至7.0莫耳。 The amount of acetic anhydride or trifluoroacetic anhydride used in this reaction can be selected from the range of 1 mole to the equivalent of the solvent relative to 1 mole of compound [I-9], preferably 1.0 to 7.0 moles .

本反應中能夠使用之溶劑可列舉例如：二***、環戊基甲醚、四氫呋喃、2-甲基四氫呋喃、1,4-二

Figure 108129126-A0202-12-0121-155
烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；甲醇、乙醇、2-丙醇 等醇類；乙腈、丙腈等腈類；乙酸乙酯等酯類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；水或此等混合溶劑等。此外，相對於化合物[I-9]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至10公升。 Examples of solvents that can be used in this reaction include: diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-bis
Figure 108129126-A0202-12-0121-155
Ethers such as alkanes; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; halogenated hydrocarbons such as methylene chloride, chloroform, and 1,2-dichloroethane; alcohols such as methanol, ethanol, and 2-propanol Nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; water or mixed solvents such as these. In addition, the amount of the solvent used is 0.1 to 100 liters, preferably 0.3 to 10 liters relative to 1 mole of compound [I-9].

於本反應中使用鹼時，能夠使用之鹼可列舉例如：氫氧化鋰、氫氧化鈉、氫氧化鉀等鹼金屬的氫氧化物類；氫氧化鈣、氫氧化鎂等鹼土類金屬的氫氧化物類；碳酸鈉、碳酸鉀等鹼金屬的碳酸鹽類等無機鹼類；甲氧化鈉、乙氧化鈉、第三丁氧化鉀等醇的金屬鹽類或三乙胺、N,N-二甲基苯胺、吡啶、4-N,N-二甲基胺基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一烯等有機鹼類等。此外，相對於化合物[I-9]1莫耳，鹼的使用量可適當地選自1至10莫耳的範圍，較佳為1.0至5.0莫耳。 When an alkali is used in this reaction, the alkali that can be used includes, for example, hydroxides of alkali metals such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide Species; inorganic alkalis such as carbonates of alkali metals such as sodium carbonate and potassium carbonate; metal salts of alcohols such as sodium methoxide, sodium ethoxide, and third potassium butoxide or triethylamine, N,N-dimethyl Organic bases such as aniline, pyridine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]-7-undecene, etc. In addition, the amount of the base used can be appropriately selected from the range of 1 to 10 moles relative to 1 mole of compound [I-9], preferably 1.0 to 5.0 moles.

於本反應中使用酸時，能夠使用之酸可列舉例如：鹽酸、氫溴酸或硫酸等無機酸類；乙酸或三氟乙酸等羧酸類等。相對於化合物[I-9]1莫耳，酸的使用量可適當地選自從1莫耳至相當於溶劑量的範圍，較佳為1至100莫耳。 When an acid is used in this reaction, examples of the acid that can be used include inorganic acids such as hydrochloric acid, hydrobromic acid, and sulfuric acid; carboxylic acids such as acetic acid and trifluoroacetic acid; The amount of the acid used can be appropriately selected from the range of 1 mole to the equivalent of the solvent relative to 1 mole of compound [I-9], preferably 1 to 100 moles.

本反應之反應溫度於任一反應中，皆可選自從-10℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於0℃至50℃的溫度範圍內進行。 The reaction temperature of this reaction can be selected from any temperature range from -10°C to the reflux temperature in the reaction system in any reaction, and preferably can be carried out in the temperature range of 0°C to 50°C.

本反應之反應時間於任一反應中，雖因反應溫度、反應基質、反應量等而有所不同，但通常為5分鐘至24小時。 The reaction time of this reaction is different in any reaction, although it varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but it is usually 5 minutes to 24 hours.

反應結束後將反應混合物注加於水中等並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[I-11]。單離出之化合物[I-11]可因應所需藉由管柱層析、再結晶等進行進一步精製。再者，化合物[I-11]亦可在不進行單離及精製下使用於下一反應(製造方法6)。 After the reaction is completed, the reaction mixture is poured into water, etc., extracted with an organic solvent, and then concentrated and the like, whereby the compound [I-11] can be isolated. The single isolated compound [I-11] can be further purified by column chromatography, recrystallization, etc. as required. In addition, the compound [I-11] can also be used for the next reaction without isolation and purification (Production Method 6).

〈製造方法6〉 <Manufacturing method 6>

本發明之化合物中，通式[I-12]所表示之化合物例如可使用通式[III-3]所表示之化合物並依循由下述所例示之反應式所組成之方法來製造。 Among the compounds of the present invention, the compound represented by the general formula [I-12] can be produced, for example, using the compound represented by the general formula [III-3] and following the method composed of the reaction formula exemplified below.

Figure 108129126-A0202-12-0123-279
Figure 108129126-A0202-12-0123-279

(式中，R3、R4、R6、Ra、Rb、L1、A及n表示與前述相同意義) (In the formula, R 3 , R 4 , R 6 , R a , R b , L 1 , A and n represent the same meaning as above)

(步驟6-1) (Step 6-1)

亦即，通式[I-12]所表示之化合物可在適當之酸的存在下，於適當的溶劑中使通式[III-3]所表示之化合物與氰酸鹽或硫氰酸鹽進行反應而形成通式[III-4]所表示之化合物後，於適當之鹼的存在下或適當之酸觸媒的存在下，於適當的溶劑中使此化合物[III-4]與化合物[IV-3]或化合物[IV-4]進行反應而製造。 That is, the compound represented by the general formula [I-12] can be carried out in the presence of an appropriate acid in a suitable solvent with the compound represented by the general formula [III-3] and cyanate or thiocyanate After the reaction to form the compound represented by the general formula [III-4], in the presence of a suitable base or a suitable acid catalyst, the compound [III-4] and the compound [IV -3] or compound [IV-4] is produced by reacting.

本反應中能夠使用之氰酸鹽或硫氰酸鹽可列舉例如：氰酸鈉、氰酸鉀、氰酸銨、硫氰酸鈉、硫氰酸鉀、硫氰酸銨等。相對於化合物[III-3]1莫耳，氰酸鹽或硫氰酸鹽的使用量可選自從1莫耳至10莫耳的範圍，較佳為1.0至6.0莫耳。 Examples of the cyanate or thiocyanate that can be used in this reaction include sodium cyanate, potassium cyanate, ammonium cyanate, sodium thiocyanate, potassium thiocyanate, and ammonium thiocyanate. The amount of cyanate or thiocyanate used can be selected from the range of 1 mol to 10 mol, preferably 1.0 to 6.0 mol, relative to 1 mol of compound [III-3].

本步驟中能夠使用之酸，可列舉例如：鹽酸或氫溴酸等無機酸類等。相對於化合物[III-4]1莫耳，酸的使用量可適當地選自從1莫耳至相當於溶劑量的範圍，較佳為1.0至10.0莫耳。 Examples of the acid that can be used in this step include inorganic acids such as hydrochloric acid and hydrobromic acid. The amount of the acid used can be appropriately selected from the range of 1 mole to the equivalent of the solvent relative to 1 mole of compound [III-4], preferably 1.0 to 10.0 mole.

本步驟中能夠使用之溶劑可列舉例如：乙腈、丙腈等腈類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇等醇類；水或此等混合溶劑等。此外，相對於化合物[III-3]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至10公升。 Examples of solvents that can be used in this step include nitriles such as acetonitrile and propionitrile; N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidine Aprotic polar solvents such as ketones, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol; water or mixtures of these Solvent, etc. In addition, the amount of the solvent used is 0.1 to 100 liters, preferably 0.3 to 10 liters relative to 1 mole of the compound [III-3].

本步驟之反應溫度可選自從-30℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於-10℃至100℃的溫度範圍內進行。 The reaction temperature in this step can be selected from any temperature range from -30°C to the reflux temperature in the reaction system, and preferably can be performed in a temperature range of -10°C to 100°C.

本步驟之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為10分鐘至20小時。 Although the reaction time in this step varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 10 minutes to 20 hours.

反應結束後將反應混合物注加於水中並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[I-12]。單離出之化合物[I-12]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water and extracted with an organic solvent, followed by concentration and other operations, whereby the compound [I-12] can be isolated. The single isolated compound [I-12] can be further purified by column chromatography, recrystallization, etc. as required.

(步驟6-2) (Step 6-2)

通式[I-12]所表示之化合物可使用與製造方法1的步驟1-3相同之條件，使通式[III-4]所表示之化合物進行反應而製造。 The compound represented by general formula [I-12] can be produced by reacting the compound represented by general formula [III-4] using the same conditions as steps 1-3 of production method 1.

〈製造方法7〉 <Manufacturing method 7>

本發明之化合物中，通式[I-14]所表示之化合物例如可使用通式[I-13]所表示之化合物並依循由下述所例示之反應式所組成之方法來製造。 Among the compounds of the present invention, the compound represented by the general formula [I-14] can be produced, for example, using the compound represented by the general formula [I-13] and following the method composed of the reaction formula exemplified below.

Figure 108129126-A0202-12-0125-280
Figure 108129126-A0202-12-0125-280

(式中，R3、R4、R5a、R6、R10、Ra、Rb及n表示與前述相同意義，Y表示氧原子、硫原子或NR10，L4表示鹵素原子、甲烷磺醯基氧基、三氟甲烷磺醯基氧基、九氟丁烷磺醯基氧基、苯磺醯基氧基、對甲苯磺醯基氧基或-S(=O)2Rb，R5b表示氟原子、C1至C6烷氧基、C1至C6鹵烷基或C1至C6鹵烷氧基) (In the formula, R 3 , R 4 , R 5a , R 6 , R 10 , R a , R b and n represent the same meaning as above, Y represents an oxygen atom, sulfur atom or NR 10 , L 4 represents a halogen atom, methane Sulfonyloxy, trifluoromethanesulfonyloxy, nonafluorobutanesulfonyloxy, benzenesulfonyloxy, p-toluenesulfonyloxy or -S(=O) 2 R b , R 5b represents a fluorine atom, C 1 to C 6 alkoxy, C 1 to C 6 haloalkyl or C 1 to C 6 haloalkoxy)

亦即，通式[I-14]所表示之化合物可藉由在適當之鹼的存在下或不存在下，適當之自由基起始劑的存在下或不存在下，於適當的溶劑中使通式[I-13]所表示之化合物與化合物[IV-11]或化合物[IV-12]進行反應而製造。 That is, the compound represented by the general formula [I-14] can be used in an appropriate solvent in the presence or absence of an appropriate base, in the presence or absence of an appropriate radical initiator The compound represented by the general formula [I-13] is reacted with the compound [IV-11] or the compound [IV-12] to produce.

相對於化合物[I-13]1莫耳，本反應中所使用之化合物[IV-11]或化合物[IV-12]的使用量可適當地選自1至20莫耳的範圍，較佳為1.1至5.5莫耳。 The amount of the compound [IV-11] or the compound [IV-12] used in this reaction can be appropriately selected from the range of 1 to 20 moles relative to 1 mole of compound [I-13], preferably 1.1 to 5.5 moles.

本反應中能夠使用之鹼可列舉例如：氫氧化鈉、氫氧化鉀、氫氧化鋰等鹼金屬的氫氧化物類；氫氧化鈣、氫氧化鎂等鹼土類金屬的氫氧化物類；碳酸鈉、碳酸鉀等鹼金屬的碳酸鹽類；碳酸氫鈉、碳酸氫鉀等鹼金屬重碳酸鹽類等無機鹼類；氫化鈉、氫化鉀等金屬氫化物類；甲氧化鈉、乙氧化鈉、第三丁氧化鉀等醇的金屬鹽類或三乙胺、N,N-二甲基苯胺、吡啶、4-N,N-二甲基胺基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一烯等有機鹼類等。此外，相對於化合物[I-13]1莫耳，鹼的使用量可適當地選自1至5莫耳的範 圍，較佳為1.0至2.0莫耳。惟，三乙胺、吡啶等有機鹼類亦可作為上述溶劑使用。本反應中能夠使用之自由基起始劑可列舉例如：亞硫酸、亞硫酸鹽、Rongalite(商品名，甲醛次硫酸氫鈉)等亞硫酸加成物等。此外，相對於化合物[I-13]1莫耳，自由基起始劑的使用量可適當地選自0.01至5莫耳的範圍，較佳為0.01至1.2莫耳。 Examples of the base that can be used in this reaction include: hydroxides of alkali metals such as sodium hydroxide, potassium hydroxide, and lithium hydroxide; hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide; and sodium carbonate , Potassium carbonate and other alkali metal carbonates; sodium bicarbonate, potassium bicarbonate and other alkali metal bicarbonates and other inorganic bases; sodium hydride, potassium hydride and other metal hydrides; sodium methoxide, sodium ethoxide, the first Metal salts of alcohols such as potassium tributoxide or triethylamine, N,N-dimethylaniline, pyridine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5.4. 0]-7-undecene and other organic bases. In addition, the amount of base used can be appropriately selected from the range of 1 to 5 moles relative to 1 mole of compound [I-13] It is preferably 1.0 to 2.0 moles. However, organic bases such as triethylamine and pyridine can also be used as the above solvents. Examples of the radical initiator that can be used in this reaction include sulfurous acid adducts such as sulfurous acid, sulfite, and Rongalite (trade name, sodium formaldehyde sulfoxylate). In addition, the amount of the radical initiator used can be appropriately selected from the range of 0.01 to 5 moles relative to 1 mole of compound [I-13], preferably 0.01 to 1.2 moles.

本反應中能夠使用之溶劑可列舉例如：二***、環戊基甲醚、四氫呋喃、2-甲基四氫呋喃、1,4-二

Figure 108129126-A0202-12-0126-136
烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；乙腈、丙腈等腈類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇等醇類；乙酸乙酯等酯類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；吡啶、甲吡啶等吡啶類；三乙胺、三丁胺等第三胺類；水或此等混合溶劑等。此外，相對於化合物[I-13]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至10公升。 Examples of solvents that can be used in this reaction include: diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-bis
Figure 108129126-A0202-12-0126-136
Ethers such as alkane; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane; nitriles such as acetonitrile and propionitrile; N, N -Dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2- Aprotic polar solvents such as imidazolidinone; alcohols such as methanol, ethanol, 2-propanol; esters such as ethyl acetate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane; pyridine, Pyridines such as picoline; third amines such as triethylamine and tributylamine; water or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 100 liters, preferably 0.3 to 10 liters relative to 1 mole of the compound [I-13].

本反應之反應溫度可選自從-30℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於0℃至150℃的範圍內進行。 The reaction temperature of this reaction can be selected from any temperature range from -30°C to the reflux temperature in the reaction system, and it is preferably carried out in the range of 0°C to 150°C.

本反應之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為10分鐘至20小時。 Although the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 10 minutes to 20 hours.

反應結束後將反應混合物注加於水中等並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[I-14]。單離出之化合物[I-14]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water, etc., extracted with an organic solvent, and then concentrated and the like, whereby the compound [I-14] can be isolated. The isolated compound [I-14] can be further purified by column chromatography, recrystallization, etc. as required.

〈製造方法8〉 <Manufacturing method 8>

本發明之化合物中，通式[I-15]所表示之化合物、通式[I-16]所表示之化合物及通式[I-17]所表示之化合物，例如可使用通式[I-2]所表示之化合物並依循由下述所例示之反應式所組成之方法來製造。 Among the compounds of the present invention, the compound represented by the general formula [I-15], the compound represented by the general formula [I-16] and the compound represented by the general formula [I-17], for example, the general formula [I- 2] The compound represented by the method is produced according to the method composed of the reaction formula exemplified below.

Figure 108129126-A0202-12-0127-281
Figure 108129126-A0202-12-0127-281

(式中，R3、R4、R5、Ra、M、L1及n表示與前述相同意義，R6a表示C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6炔基或C3至C6環烷基) (In the formula, R 3 , R 4 , R 5 , R a , M, L 1 and n represent the same meaning as described above, R 6a represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 To C 6 alkenyl, C 2 to C 6 alkynyl or C 3 to C 6 cycloalkyl)

(步驟8-1) (Step 8-1)

亦即，通式[I-15]所表示之化合物可使用與製造方法3的步驟3-1相同之條件，使通式[I-2]所表示之化合物進行反應而製造。 That is, the compound represented by the general formula [I-15] can be produced by reacting the compound represented by the general formula [I-2] using the same conditions as in step 3-1 of the production method 3.

(步驟8-2) (Step 8-2)

再者，通式[I-16]所表示之化合物可使用與製造方法3的步驟3-2相同之條件，使通式[I-2]所表示之化合物進行反應而製造。 The compound represented by the general formula [I-16] can be produced by reacting the compound represented by the general formula [I-2] using the same conditions as in step 3-2 of the production method 3.

(步驟8-3) (Step 8-3)

再者，通式[I-17]所表示之化合物可使用與製造方法3的步驟3-3相同之條件，使通式[I-2]所表示之化合物進行反應而製造。 The compound represented by the general formula [I-17] can be produced by reacting the compound represented by the general formula [I-2] using the same conditions as in step 3-3 of the production method 3.

〈製造方法9〉 <Manufacturing method 9>

本發明之化合物中，通式[I-1]所表示之化合物例如可使用通式[I-2]所表示之化合物並依循由下述所例示之反應式所組成之方法來製造。 Among the compounds of the present invention, the compound represented by the general formula [I-1] can be produced, for example, using the compound represented by the general formula [I-2] and following the method composed of the reaction formula exemplified below.

Figure 108129126-A0202-12-0128-282
Figure 108129126-A0202-12-0128-282

(式中，R3、R4、R5、R6、Ra及n表示與前述相同意義) (Wherein, R 3, R 4, R 5, R 6, R a and n represent the same meaning as aforementioned)

亦即，通式[I-1]所表示之化合物可藉由在適當之溶劑的存在下或不存在下、適當之鹼的存在下或不存在下、適當之酸的存在下或不存在下、適當之脫水縮合劑的存在下或不存在下，使通式[I-2]所表示之化合物與適當的親電子試劑進行反應而製造。 That is, the compound represented by the general formula [I-1] can be prepared by the presence or absence of an appropriate solvent, the presence or absence of an appropriate base, the presence or absence of an appropriate acid 1. In the presence or absence of a suitable dehydrating condensation agent, the compound represented by the general formula [I-2] is reacted with a suitable electrophilic reagent to produce.

相對於化合物[I-2]1莫耳，本反應中所使用之親電子試劑的使用量可適當地選自從1莫耳至相當於溶劑量的範圍，較佳為1至150莫耳。 The use amount of the electrophile used in the present reaction can be appropriately selected from the range of 1 mole to the equivalent of the solvent, preferably 1 to 150 moles relative to 1 mole of the compound [I-2].

於本反應中使用鹼時，能夠使用之鹼可列舉例如：氫氧化鈉、氫氧化鉀、氫氧化鋰等鹼金屬的氫氧化物類；氫氧化鈣、氫氧化鎂等鹼土類金屬的氫氧化物類；碳酸鈉、碳酸鉀等鹼金屬的碳酸鹽類；碳酸氫鈉、碳酸氫 鉀等鹼金屬的重碳酸鹽類等無機鹼類；氫化鈉、氫化鉀等金屬氫化物類；甲氧化鈉、乙氧化鈉、第三丁氧化鉀等醇的金屬鹽類或三乙胺、N,N-二甲基苯胺、吡啶、4-N,N-二甲基胺基吡啶、1,8-二氮雜雙環[5,4,0]-7-十一烯等有機鹼類等。此外，在使用鹼時，相對於化合物[I-2]1莫耳，鹼的使用量可適當地選自0.01至5莫耳的範圍，較佳為0.1至3.0莫耳。 When an alkali is used in this reaction, the alkali that can be used includes, for example, hydroxides of alkali metals such as sodium hydroxide, potassium hydroxide, and lithium hydroxide; hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide Types; carbonates of alkali metals such as sodium carbonate and potassium carbonate; sodium bicarbonate and bicarbonate Inorganic bases such as bicarbonates of alkali metals such as potassium; metal hydrides such as sodium hydride and potassium hydride; metal salts of alcohols such as sodium methoxide, sodium ethoxide and third potassium butoxide or triethylamine and N , N-dimethylaniline, pyridine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5,4,0]-7-undecene and other organic bases. In addition, when a base is used, the amount of the base used can be appropriately selected from the range of 0.01 to 5 moles relative to 1 mole of the compound [I-2], preferably 0.1 to 3.0 moles.

於本反應中使用酸時，能夠使用之酸為路易斯酸可列舉例如：甲烷磺酸或對甲苯磺酸等磺酸類；鹽酸、氫溴酸或硫酸等無機酸類；乙酸或三氟乙酸等羧酸類等。此外，相對於化合物[I-2]1莫耳，酸的使用量可適當地選自0.001至5莫耳的範圍，較佳為0.01至2.0莫耳。 When an acid is used in this reaction, the acid that can be used is a Lewis acid. Examples include sulfonic acids such as methanesulfonic acid or p-toluenesulfonic acid; inorganic acids such as hydrochloric acid, hydrobromic acid, or sulfuric acid; and carboxylic acids such as acetic acid or trifluoroacetic acid. Wait. In addition, the amount of acid used can be appropriately selected from the range of 0.001 to 5 mols relative to 1 mol of the compound [I-2], preferably 0.01 to 2.0 mols.

於本反應中使用脫水縮合劑時，能夠使用之脫水縮合劑可列舉例如：N,N’-二環己基碳二亞胺、1-乙基-3-(3-二甲基胺基丙基)碳二亞胺鹽酸鹽、1-乙基-3-(3-二甲基胺基丙基)碳二亞胺、O-(苯并***-1-基)-N,N,N’,N’-四甲基脲鹽六氟磷酸酯、氯化4-(4,6-二甲氧基-1,3,5-三

Figure 108129126-A0202-12-0129-156
-2-基)-4-甲基嗎啉鹽、1-羥基苯并***或此等混合物等。此外，相對於化合物[I-2]1莫耳，脫水縮合劑的使用量可分別適當地選自1至3莫耳的範圍，較佳分別為1.0至1.2莫耳。 When a dehydrating condensing agent is used in this reaction, examples of dehydrating condensing agents that can be used include: N,N'-dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl )Carbodiimide hydrochloride, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, O-(benzotriazol-1-yl)-N,N,N ',N'-Tetramethylurea salt hexafluorophosphate, 4-(4,6-dimethoxy-1,3,5-trichloride)
Figure 108129126-A0202-12-0129-156
-2-yl)-4-methylmorpholine salt, 1-hydroxybenzotriazole, or a mixture of these. In addition, the use amount of the dehydrating condensing agent can be appropriately selected from the range of 1 to 3 moles relative to 1 mole of the compound [I-2], preferably 1.0 to 1.2 moles, respectively.

本反應中能夠使用之溶劑可列舉例如：二***、環戊基甲醚、四氫呋喃、2-甲基四氫呋喃、1,4-二

Figure 108129126-A0202-12-0129-157
烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；乙腈、丙腈等腈類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇等醇類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；戊烷、己烷、環己烷、庚烷等脂肪族烴類或此等混合溶劑 等。此外，相對於化合物[I-2]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至20公升。 Examples of solvents that can be used in this reaction include: diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-bis
Figure 108129126-A0202-12-0129-157
Ethers such as alkanes; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile and propionitrile; N,N-dimethylformamide, N,N-dimethylacetamide, Aprotic polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; methanol, ethanol, 2-propanol Alcohols such as dichloromethane, chloroform, 1,2-dichloroethane and other halogenated hydrocarbons; pentane, hexane, cyclohexane, heptane and other aliphatic hydrocarbons or mixed solvents. In addition, the amount of the solvent used is 0.1 to 100 liters relative to 1 mol of the compound [I-2], preferably 0.3 to 20 liters.

本反應之反應溫度可選自從-20℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於0℃至150℃的範圍內進行。 The reaction temperature of this reaction can be selected from any temperature range from -20°C to the reflux temperature in the reaction system, and it can preferably be carried out in the range of 0°C to 150°C.

本反應之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為15分鐘至24小時。 Although the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 15 minutes to 24 hours.

反應結束後將反應混合物注加於水中並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[I-1]。單離出之化合物[I-1]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water and extracted with an organic solvent, followed by concentration and other operations, whereby the compound [I-1] can be isolated. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc. as required.

〈製造方法10〉 <Manufacturing method 10>

本發明之化合物中，通式[I-1]所表示之化合物例如可使用通式[I-18]所表示之化合物並依循由下述所例示之反應式所組成之方法來製造。 Among the compounds of the present invention, the compound represented by the general formula [I-1] can be produced, for example, using the compound represented by the general formula [I-18] and following the method composed of the reaction formula exemplified below.

Figure 108129126-A0202-12-0130-283
Figure 108129126-A0202-12-0130-283

(式中，R3、R4、R5、R6、Ra及n表示與前述相同意義，L5表示氫原子、鹵素原子、甲基硫基、甲基亞磺醯基、甲基磺醯基或對甲苯磺醯基等) (Wherein, R 3, R 4, R 5, R 6, R a and n represent the same meaning, L 5 represents a hydrogen atom, a halogen atom, a methylthio group, methylsulfinyl acyl, sulfo methyl (Acyl or p-toluenesulfonyl, etc.)

亦即，通式[I-1]所表示之本發明之化合物，可藉由在適當之鹼的存在下或不存在下，於適當的溶劑中使通式[I-18]所表示之化合物與化合物[IV-15]進行反應而製造。 That is, the compound of the present invention represented by the general formula [I-1] can be prepared by using the compound represented by the general formula [I-18] in an appropriate solvent in the presence or absence of an appropriate base It is produced by reacting with compound [IV-15].

相對於化合物[I-18]1莫耳，於本反應中所使用之化合物[IV-15]的使用量可適當地選自從1莫耳至相當於溶劑量的範圍，較佳為1.0至10.0莫耳。 The use amount of the compound [IV-15] used in this reaction can be appropriately selected from the range from 1 mole to the equivalent amount of the solvent relative to 1 mole of the compound [I-18], preferably 1.0 to 10.0 Moore.

於本反應中使用鹼時，能夠使用之鹼可列舉例如：氫氧化鈉、氫氧化鉀、氫氧化鋰等鹼金屬的氫氧化物類；氫氧化鈣、氫氧化鎂等鹼土類金屬的氫氧化物類；碳酸鈉、碳酸鉀等鹼金屬的碳酸鹽類；碳酸氫鈉、碳酸氫鉀等鹼金屬的重碳酸鹽類等無機鹼類；氫化鈉、氫化鉀等金屬氫化物類；甲氧化鈉、乙氧化鈉、第三丁氧化鉀等醇的金屬鹽類或三乙胺、N,N-二甲基苯胺、吡啶、4-N,N-二甲基胺基吡啶、1,8-二氮雜雙環[5,4,0]-7-十一烯等有機鹼類等。此外，相對於化合物[I-18]1莫耳，鹼的使用量可適當地選自1至10莫耳的範圍，較佳為1.0至3.0莫耳。 When an alkali is used in this reaction, the alkali that can be used includes, for example, hydroxides of alkali metals such as sodium hydroxide, potassium hydroxide, and lithium hydroxide; hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide Species; carbonates of alkali metals such as sodium carbonate and potassium carbonate; inorganic bases such as bicarbonates of alkali metals such as sodium bicarbonate and potassium bicarbonate; metal hydrides such as sodium hydride and potassium hydride; sodium methoxide , Sodium ethoxide, potassium tributoxide and other metal salts of alcohol or triethylamine, N,N-dimethylaniline, pyridine, 4-N,N-dimethylaminopyridine, 1,8-di Organic bases such as azabicyclo[5,4,0]-7-undecene. In addition, the amount of the base used can be appropriately selected from the range of 1 to 10 mols relative to 1 mol of the compound [I-18], preferably 1.0 to 3.0 mols.

本反應中能夠使用之溶劑可列舉例如：二***、環戊基甲醚、四氫呋喃、2-甲基四氫呋喃、1,4-二

Figure 108129126-A0202-12-0131-158
烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；乙腈、丙腈等腈類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇等醇類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；丙酮、丁酮、環己酮等酮類；水或此等混合溶劑等。此外，相對於化合物[I-18]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至20公升。 Examples of solvents that can be used in this reaction include: diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-bis
Figure 108129126-A0202-12-0131-158
Ethers such as alkanes; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile and propionitrile; N,N-dimethylformamide, N,N-dimethylacetamide, Aprotic polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; methanol, ethanol, 2-propanol Alcohols; dichloromethane, chloroform, 1,2-dichloroethane and other halogenated hydrocarbons; pentane, hexane, cyclohexane, heptane and other aliphatic hydrocarbons; acetone, butanone, cyclohexanone, etc. Ketones; water or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 100 liters relative to 1 mol of the compound [I-18], preferably 0.3 to 20 liters.

本反應之反應溫度可選自從-20℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於-10℃至150℃的範圍內進行。 The reaction temperature of this reaction can be selected from any temperature range from -20°C to the reflux temperature in the reaction system, and it can preferably be carried out in the range of -10°C to 150°C.

本反應之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為15分鐘至20小時。 Although the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 15 minutes to 20 hours.

反應結束後將反應混合物注加於水中並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[I-1]。單離出之化合物[I-1]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water and extracted with an organic solvent, followed by concentration and other operations, whereby the compound [I-1] can be isolated. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc. as required.

〈製造方法11〉 <Manufacturing method 11>

本發明之化合物中，通式[I-1]所表示之化合物例如可使用通式[IV-16]所表示之化合物並依循由下述所例示之反應式所組成之方法來製造。 Among the compounds of the present invention, the compound represented by the general formula [I-1] can be produced, for example, using the compound represented by the general formula [IV-16] and following the method composed of the reaction formula exemplified below.

Figure 108129126-A0202-12-0132-284
Figure 108129126-A0202-12-0132-284

(式中，R3、R4、R5、R6、Ra及n表示與前述相同意義，L6表示鹵素原子、甲烷磺醯基氧基、三氟甲烷磺醯基氧基、九氟丁烷磺醯基氧基、苯磺醯基氧基、對甲苯磺醯基氧基、二甲基胺磺醯基氧基、二羥基氧硼基(B(OH)2)或頻那醇硼烷-2-基(Pinacolborane-2-yl)等) (Wherein, R 3, R 4, R 5, R 6, R a and n represent the same meaning, L 6 represents a halogen atom, acyl group methane sulfonic, trifluoromethane sulfonic acyl group, nonafluoro Butanesulfonyloxy, benzenesulfonyloxy, p-toluenesulfonyloxy, dimethylaminesulfonyloxy, dihydroxyoxyboron (B(OH) 2 ) or pinacol boron (Pinacolborane-2-yl) etc.)

亦即，通式[I-1]所表示之化合物可藉由依據國際公開專利公報WO2006/043635號或歐洲專利公報EP3002279號所記載之方法或其方法，使化合物[IV-16]與化合物[IV-17]進行芳香族親核取代反應或交叉偶合反應而製造。 That is, the compound represented by the general formula [I-1] can make the compound [IV-16] and the compound [by the method described in International Publication Patent Publication WO2006/043635 or European Patent Publication EP3002279 or its method IV-17] Manufactured by performing aromatic nucleophilic substitution reaction or cross-coupling reaction.

〈製造方法12〉 <Manufacturing method 12>

本發明之化合物中，通式[II-2]所表示之化合物例如可使用通式[III-4]所表示之化合物並依循由下述所例示之反應式所組成之方法來製造。 Among the compounds of the present invention, the compound represented by the general formula [II-2] can be produced, for example, using the compound represented by the general formula [III-4] and following the method composed of the reaction formula exemplified below.

Figure 108129126-A0202-12-0133-285
Figure 108129126-A0202-12-0133-285

(式中，R3、R4、R5、R6、Z、p1及n表示與前述相同意義，X表示鹵素原子，Rd表示C1至C6烷基、苯基或無取代或經(Z)p1取代之苯基C1至C6烷基等) (In the formula, R 3 , R 4 , R 5 , R 6 , Z, p 1 and n represent the same meaning as described above, X represents a halogen atom, R d represents C 1 to C 6 alkyl, phenyl or unsubstituted or Phenyl C 1 to C 6 alkyl substituted with (Z)p 1 etc.)

亦即，通式[II-2]所表示之化合物可藉由在適當之觸媒的存在下或不存在下，於適當的溶劑中使通式[III-5]所表示之化合物氰基化而形成通式[III-6]所表示之化合物後，在適當之酸或鹼的存在下，於適當的溶劑中進行水解反應而製造。 That is, the compound represented by the general formula [II-2] can be cyanated by the compound represented by the general formula [III-5] in the presence or absence of an appropriate catalyst in an appropriate solvent After forming the compound represented by the general formula [III-6], it is produced by carrying out a hydrolysis reaction in an appropriate solvent in the presence of an appropriate acid or base.

(步驟12-1) (Step 12-1)

本步驟中所使用之氰化合物可列舉例如：氰化鈉、氰化鉀、氰化銨、氰化鋅、氰化銅、或此等混合物。此外，相對於化合物[III-5]1莫耳，氰化合物的使用量通常可適當地選自1至100莫耳的範圍，較佳為1.0至5.0莫耳。 Examples of the cyanide compound used in this step include sodium cyanide, potassium cyanide, ammonium cyanide, zinc cyanide, copper cyanide, and mixtures thereof. In addition, the amount of the cyanide compound used may be appropriately selected from the range of 1 to 100 moles relative to 1 mole of compound [III-5], preferably 1.0 to 5.0 moles.

本步驟中所使用之觸媒可列舉例如：四(三苯基膦)鈀。此外，相對於化合物[III-5]1莫耳，觸媒的使用量通常可適當地選自0.001至0.5莫耳的範圍，較佳為0.01至0.1莫耳。 Examples of the catalyst used in this step include tetrakis(triphenylphosphine)palladium. In addition, the amount of the catalyst used can be appropriately selected from the range of 0.001 to 0.5 mol, preferably 0.01 to 0.1 mol, relative to 1 mol of the compound [III-5].

本步驟中能夠使用之溶劑可列舉例如：二***、環戊基甲醚、四氫呋喃、2-甲基四氫呋喃、1,4-二

Figure 108129126-A0202-12-0134-159
烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；乙腈、丙腈等腈類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇等醇類；乙酸乙酯等酯類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；吡啶、甲吡啶等吡啶類；水、或此等混合溶劑等。此外，相對於化合物[III-5]1莫耳，溶劑的使用量為0.1至500公升，較佳為0.3至50公升。 Examples of solvents that can be used in this step include: diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-bis
Figure 108129126-A0202-12-0134-159
Ethers such as alkane; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane; nitriles such as acetonitrile and propionitrile; N, N -Dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2- Aprotic polar solvents such as imidazolidinone; alcohols such as methanol, ethanol, 2-propanol; esters such as ethyl acetate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane; pyridine, Pyridines such as picoline; water, or mixed solvents such as these. In addition, the amount of the solvent used is 0.1 to 500 liters relative to 1 mole of the compound [III-5], preferably 0.3 to 50 liters.

本步驟之反應溫度通常可選自從-30℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於0℃至150℃的範圍內進行。 The reaction temperature in this step can be generally selected from any temperature range from -30°C to the reflux temperature in the reaction system, and preferably can be performed in the range of 0°C to 150°C.

本步驟之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為10分鐘至72小時。 Although the reaction time in this step varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 10 minutes to 72 hours.

反應結束後將反應混合物注加於水中，濾取所析出之固體或利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[III-6]。單離出之化合物[III-6]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water, and the precipitated solid is filtered off or extracted with an organic solvent and then concentrated, and the compound [III-6] can be isolated. The isolated compound [III-6] can be further purified by column chromatography, recrystallization, etc. as required.

(步驟12-2) (Step 12-2)

本步驟中能夠使用之酸可列舉例如：鹽酸、氫溴酸或硫酸等無機酸類；乙酸或三氟乙酸等羧酸類；甲烷磺酸或三氟甲烷磺酸等磺酸類等。此外，相對於化合物[III-6]1莫耳，酸的使用量可適當地選自從1至相當於溶劑量莫耳的範圍較佳為1.0至100.0莫耳。 Examples of the acid that can be used in this step include inorganic acids such as hydrochloric acid, hydrobromic acid, and sulfuric acid; carboxylic acids such as acetic acid or trifluoroacetic acid; and sulfonic acids such as methanesulfonic acid or trifluoromethanesulfonic acid. In addition, the amount of acid used can be appropriately selected from the range of 1 to a molar amount equivalent to the solvent relative to 1 mole of the compound [III-6], preferably 1.0 to 100.0 moles.

本步驟中能夠使用之鹼可列舉例如：氫氧化鈉、氫氧化鉀、氫氧化鋰等鹼金屬的氫氧化物類；碳酸鈉、碳酸鉀等鹼金屬的碳酸鹽類；碳酸氫鈉、碳酸氫鉀等鹼金屬的重碳酸鹽類等無機鹼類等。此外，相對於化合物[III-6]1莫耳，鹼的使用量可適當地選自0.1至50莫耳的範圍，較佳為0.5至20.0莫耳。 Examples of the base that can be used in this step include: hydroxides of alkali metals such as sodium hydroxide, potassium hydroxide, and lithium hydroxide; carbonates of alkali metals such as sodium carbonate and potassium carbonate; sodium bicarbonate and hydrogen carbonate Inorganic bases such as potassium bicarbonate and other alkali metals. In addition, the amount of the base used can be appropriately selected from the range of 0.1 to 50 moles, preferably 0.5 to 20.0 moles relative to 1 mole of compound [III-6].

本步驟中能夠使用之溶劑可列舉例如：二***、環戊基甲醚、四氫呋喃、2-甲基四氫呋喃、1,4-二

Figure 108129126-A0202-12-0135-160
烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；乙腈、丙腈等腈類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇等醇類；丙酮、丁酮、環己酮等酮類；水、或此等混合溶劑等。此外，相對於化合物[III-6]1莫耳，溶劑的使用量為0.1至500公升，較佳為0.3至30公升。 Examples of solvents that can be used in this step include: diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-bis
Figure 108129126-A0202-12-0135-160
Ethers such as alkanes; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile and propionitrile; N,N-dimethylformamide, N,N-dimethylacetamide, Aprotic polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; methanol, ethanol, 2-propanol Alcohols; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; water, or mixed solvents such as these. In addition, the amount of the solvent used is 0.1 to 500 liters relative to 1 mole of compound [III-6], preferably 0.3 to 30 liters.

本步驟之反應溫度通常可選自從-30℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於0℃至150℃的範圍內進行。 The reaction temperature in this step can be generally selected from any temperature range from -30°C to the reflux temperature in the reaction system, and preferably can be performed in the range of 0°C to 150°C.

本步驟之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為10分鐘至72小時。 Although the reaction time in this step varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 10 minutes to 72 hours.

反應結束後將反應混合物注加於水中並中和後，濾取所析出之固體或利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[II-2]。單離出之化合物[II-2]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water and neutralized, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated, thereby isolating compound [II-2]. The isolated compound [II-2] can be further purified by column chromatography, recrystallization, etc. as required.

(步驟12-3) (Step 12-3)

此外，通式[II-2]所表示之化合物可依據J.Organometal.Chem.,358卷，563頁至565頁(1988年)所記載之方法或其方法，並且藉由使用鈀等過渡金屬觸媒之CO***反應來製造。 In addition, the compound represented by the general formula [II-2] can be based on the method described in J. Organometal.Chem., volume 358, pages 563 to 565 (1988) or its method, and by using a transition metal such as palladium The catalyst is produced by CO insertion reaction.

再者，通式[II-2]所表示之化合物可依據Chem.Rev.,90卷，879頁至933頁(1990年)所記載之方法或其方法，並解藉由在鋰化後與碳酸氣體反應而製造。 Furthermore, the compound represented by the general formula [II-2] can be based on the method described in Chem. Rev., Volume 90, pages 879 to 933 (1990) or its method, and the solution can be Carbonate gas is produced by reaction.

(步驟12-4) (Step 12-4)

進一步，通式[II-2]所表示之化合物可依據J.Org.Chem.,39卷，3318頁至3326頁(1974年)所記載之方法或其方法，並且藉由使用鈀等過渡金屬觸媒之CO***反應來形成通式[II-1]所表示之化合物後，在適當之酸或鹼的存在下，於適當的溶劑中進行水解反應而製造。 Further, the compound represented by the general formula [II-2] can be based on the method described in J. Org. Chem., Volume 39, pages 3318 to 3326 (1974) or its method, and by using a transition metal such as palladium After the CO insertion reaction of the catalyst to form the compound represented by the general formula [II-1], it is produced by performing a hydrolysis reaction in an appropriate solvent in the presence of an appropriate acid or base.

(步驟12-5) (Step 12-5)

本步驟中能夠使用之酸、鹼、溶劑、反應溫度及反應時間係與步驟12-2相同。 The acid, base, solvent, reaction temperature and reaction time that can be used in this step are the same as in step 12-2.

反應結束後將反應混合物注加於水中並中和後，濾取所析出之固體或利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[II-2]。單離出之化合物[II-2]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water and neutralized, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated, thereby isolating compound [II-2]. The isolated compound [II-2] can be further purified by column chromatography, recrystallization, etc. as required.

〈製造方法13〉 <Manufacturing method 13>

本發明之化合物中，通式[I-19]所表示之化合物例如可使用通式[II-2]所表示之化合物並依循由下述所例示之反應式所組成之方法來製造。 Among the compounds of the present invention, the compound represented by the general formula [I-19] can be produced, for example, using the compound represented by the general formula [II-2] and following the method composed of the reaction formula exemplified below.

Figure 108129126-A0202-12-0137-286
Figure 108129126-A0202-12-0137-286

(式中，R1、R2、R3、R4、R5、R6、Rb及n表示與前述相同意義，L7表示鹵素原子、-OC(=O)ORb、甲烷磺醯基氧基、三氟甲烷磺醯基氧基、苯磺醯基氧基或對甲苯磺醯基氧基) (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R b and n represent the same meaning as above, L 7 represents a halogen atom, -OC(=O)OR b , methanesulfonamide Yloxy, trifluoromethanesulfonyloxy, benzenesulfonyloxy or p-toluenesulfonyloxy)

(步驟13-1) (Step 13-1)

亦即，通式[I-19]所表示之化合物可藉由在適當之脫水縮合劑及適當之鹼的存在下或不存在下，於適當的溶劑中使通式[II-2]所表示之化合物與化合物[IV-18]進行反應而製造。 That is, the compound represented by the general formula [I-19] can be represented by the general formula [II-2] in the presence or absence of an appropriate dehydration condensing agent and an appropriate base in an appropriate solvent The compound is produced by reacting the compound [IV-18].

相對於化合物[II-2]1莫耳，本步驟中所使用之化合物[IV-18]的使用量可適當地選自1至10莫耳的範圍，較佳為1.0至5.0莫耳。 The use amount of the compound [IV-18] used in this step can be appropriately selected from the range of 1 to 10 moles, preferably 1.0 to 5.0 moles relative to 1 mole of the compound [II-2].

本步驟中能夠使用之脫水縮合劑可列舉例如：N,N’-二環己基碳二亞胺、1-乙基-3-(3-二甲基胺基丙基)碳二亞胺鹽酸鹽、1-乙基-3-(3-二甲基胺 基丙基)碳二亞胺、O-(苯并***-1-基)-N,N,N',N’-四甲基脲鹽六氟磷酸酯、氯化4-(4,6-二甲氧基-1,3,5-三

Figure 108129126-A0202-12-0138-161
-2-基)-4-甲基嗎啉鹽、1-羥基苯并***或此等混合物等。此外，相對於化合物[II-2]1莫耳，脫水縮合劑的使用量分別可適當地選自1至5莫耳的範圍，較佳分別為1.0至3.0莫耳。 Examples of dehydrating condensation agents that can be used in this step include: N,N'-dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloric acid Salt, 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide, O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyl Urea salt hexafluorophosphate, 4-(4,6-dimethoxy-1,3,5-trichloride)
Figure 108129126-A0202-12-0138-161
-2-yl)-4-methylmorpholine salt, 1-hydroxybenzotriazole, or a mixture of these. In addition, the use amount of the dehydrating condensing agent can be appropriately selected from the range of 1 to 5 moles relative to 1 mole of the compound [II-2], preferably 1.0 to 3.0 moles, respectively.

於本步驟中使用鹼時，能夠使用之鹼可列舉例如：三乙胺、4-甲基嗎啉、二異丙基乙胺、1,8-二氮雜雙環[5.4.0]-7-十一烯、吡啶、4-N,N-二甲基胺基吡啶、2,6-二甲基吡啶(Lutidine)等有機鹼類等。此外，相對於化合物[II-2]1莫耳，鹼的使用量可適當地選自0.1至5莫耳的範圍，較佳為0.1至3.0莫耳。 When a base is used in this step, examples of usable bases include triethylamine, 4-methylmorpholine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7- Organic bases such as undecene, pyridine, 4-N,N-dimethylaminopyridine, 2,6-lutidine (Lutidine), etc. In addition, the amount of the base used can be appropriately selected from the range of 0.1 to 5 moles relative to 1 mole of the compound [II-2], preferably 0.1 to 3.0 moles.

本步驟中能夠使用之溶劑可列舉例如：二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；乙酸乙酯等酯類；乙腈、丙腈等腈類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮等非質子性極性溶劑類；二***、環戊基甲醚、四氫呋喃、2-甲基四氫呋喃、1,4-二

Figure 108129126-A0202-12-0138-162
烷等醚類或此等混合溶劑等。此外，相對於化合物[II-2]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至50公升。 Examples of solvents that can be used in this step include: dichloromethane, chloroform, 1,2-dichloroethane and other halogenated hydrocarbons; pentane, hexane, cyclohexane, heptane and other aliphatic hydrocarbons; ethyl acetate Esters such as esters; nitriles such as acetonitrile and propionitrile; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylmethylene Aprotic polar solvents such as citric acid, cyclobutane, 1,3-dimethyl-2-imidazolidinone; diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-di
Figure 108129126-A0202-12-0138-162
Ethers such as alkanes or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 100 liters, preferably 0.3 to 50 liters relative to 1 mole of the compound [II-2].

本步驟可因應所需在觸媒的存在下進行，觸媒可適當地選自4-N,N-二甲基胺基吡啶等。此外，相對於化合物[II-2]1莫耳，所使用之觸媒的使用量可適當地選自0.001至1莫耳的範圍，較佳為0.01至0.1莫耳。 This step can be carried out in the presence of a catalyst as needed, and the catalyst can be appropriately selected from 4-N,N-dimethylaminopyridine and the like. In addition, the amount of the catalyst used can be appropriately selected from the range of 0.001 to 1 mol, preferably 0.01 to 0.1 mol, relative to 1 mol of the compound [II-2].

本步驟之反應溫度可選自從-20℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於0℃至80℃的範圍內進行。 The reaction temperature in this step can be selected from any temperature range from -20°C to the reflux temperature in the reaction system, and preferably can be performed in the range of 0°C to 80°C.

本步驟之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為1分鐘至100小時。 Although the reaction time in this step varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 1 minute to 100 hours.

反應結束後將反應混合物注加於水中並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[I-19]。單離出之化合物[I-19]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water and extracted with an organic solvent, followed by concentration and other operations, whereby the compound [I-19] can be isolated. The single isolated compound [I-19] can be further purified by column chromatography, recrystallization, etc. as required.

(步驟13-2) (Step 13-2)

再者，通式[I-19]所表示之本發明之化合物，可藉由在適當之觸媒的存在下或不存在下，於適當的溶劑中將通式[II-2]所表示之化合物轉換為屬於酸鹵化物或混合酸酐等活性衍生物的化合物[II-3]後，在適當之鹼的存在下，於適當的溶劑中與化合物[IV-18]進行反應而製造。 Furthermore, the compound of the present invention represented by the general formula [I-19] can be represented by the general formula [II-2] in an appropriate solvent in the presence or absence of an appropriate catalyst After the compound is converted to the compound [II-3] which is an active derivative such as acid halide or mixed acid anhydride, it is produced by reacting with the compound [IV-18] in an appropriate solvent in the presence of an appropriate base.

為了將化合物[II-2]轉換為酸鹵化物，可使用亞硫醯氯(Thionyl Chloride)或草醯氯(Oxalyl Chloride)等。其他轉換為活性衍生物之試劑可使用氯碳酸異丁酯、氯化甲烷磺醯、氯化三氟甲烷磺醯、氯化對甲苯磺醯等。此外，相對於化合物[II-2]1莫耳，轉換為活性衍生物之試劑的使用量可適當地選自0.5至5莫耳的範圍，較佳為0.5至2.2莫耳。 In order to convert the compound [II-2] to an acid halide, Thionyl Chloride, Oxalyl Chloride, or the like can be used. Other reagents converted to active derivatives can be isobutyl chlorocarbonate, methanesulfonamide chloride, trifluoromethanesulfonamide chloride, p-toluenesulfonamide chloride, etc. In addition, the amount of the agent converted into the active derivative is suitably selected from the range of 0.5 to 5 moles, preferably 0.5 to 2.2 moles relative to 1 mole of compound [II-2].

於本步驟中使用觸媒時，能夠使用之觸媒可列舉例如：N,N-二甲基甲醯胺等。此外，相對於化合物[II-2]1莫耳，觸媒的使用量可適當地選自0.01至1莫耳的範圍，較佳為0.01至0.3莫耳。 When a catalyst is used in this step, examples of the catalyst that can be used include N,N-dimethylformamide and the like. In addition, the amount of the catalyst used can be appropriately selected from the range of 0.01 to 1 mol, preferably 0.01 to 0.3 mol, relative to 1 mol of the compound [II-2].

本步驟中能夠使用之溶劑可列舉例如：二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；苯、甲苯、二甲苯、氯苯等芳香族烴類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；乙腈、丙腈等腈類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪 唑啶酮等非質子性極性溶劑類；二***、環戊基甲醚、四氫呋喃、2-甲基四氫呋喃、1,4-二

Figure 108129126-A0202-12-0140-168
烷等醚類或此等混合溶劑等。此外，相對於化合物[II-2]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至10公升。 Examples of solvents that can be used in this step include: dichloromethane, chloroform, 1,2-dichloroethane and other halogenated hydrocarbons; benzene, toluene, xylene, chlorobenzene and other aromatic hydrocarbons; pentane and hexane , Cyclohexane, heptane and other aliphatic hydrocarbons; acetonitrile, propionitrile and other nitriles; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2- Aprotic polar solvents such as pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyl Tetrahydrofuran, 1,4-di
Figure 108129126-A0202-12-0140-168
Ethers such as alkanes or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 100 liters, preferably 0.3 to 10 liters relative to 1 mole of the compound [II-2].

本步驟之反應溫度可選自從-20℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於0℃至80℃的範圍內進行。 The reaction temperature in this step can be selected from any temperature range from -20°C to the reflux temperature in the reaction system, and preferably can be performed in the range of 0°C to 80°C.

本步驟之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為1分鐘至48小時。 Although the reaction time in this step varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 1 minute to 48 hours.

反應結束後藉由進行濃縮等操作，可單離出化合物[II-3]。 After the reaction, the compound [II-3] can be isolated by performing operations such as concentration.

(步驟13-3) (Step 13-3)

於含有所得到之化合物[II-3]之反應溶液中，通常，在適當之鹼的存在下，於適當的溶劑中使化合物[IV-18]反應，藉此可製造化合物[I-19]。 In the reaction solution containing the obtained compound [II-3], usually, the compound [IV-18] is reacted in an appropriate solvent in the presence of a suitable base, whereby the compound [I-19] can be produced .

相對於化合物[II-2]1莫耳，本步驟中所使用之化合物[IV-18]的使用量可適當地選自1至3莫耳的範圍，較佳為1.0至2.5莫耳。 The use amount of the compound [IV-18] used in this step can be appropriately selected from the range of 1 to 3 moles, preferably 1.0 to 2.5 moles relative to 1 mole of the compound [II-2].

本步驟中能夠使用之鹼可列舉例如：氫氧化鈉、氫氧化鉀、氫氧化鋰等鹼金屬的氫氧化物類；碳酸鈉、碳酸鉀等鹼金屬的碳酸鹽類；碳酸氫鈉、碳酸氫鉀等鹼金屬的重碳酸鹽類等無機鹼類；氫化鈉、氫化鉀等金屬氫化物類或三乙胺、N,N-二甲基苯胺、吡啶、4-N,N-二甲基胺基吡啶、1,8-二氮雜雙環[5,4,0]-7-十一烯等有機鹼類等。此外，相對於化合物[II-2]1莫耳，鹼的使用量可適當地選自1至5莫耳的範圍，較佳為1.0至2.5莫耳。 Examples of the base that can be used in this step include: hydroxides of alkali metals such as sodium hydroxide, potassium hydroxide, and lithium hydroxide; carbonates of alkali metals such as sodium carbonate and potassium carbonate; sodium bicarbonate and hydrogen carbonate Inorganic bases such as potassium and other alkali metal bicarbonates; metal hydrides such as sodium hydride and potassium hydride or triethylamine, N,N-dimethylaniline, pyridine, 4-N,N-dimethylamine Organic bases such as pyridine, 1,8-diazabicyclo[5,4,0]-7-undecene, etc. In addition, the amount of the base used can be appropriately selected from the range of 1 to 5 moles relative to 1 mole of compound [II-2], preferably 1.0 to 2.5 moles.

本步驟中能夠使用之溶劑可列舉例如：二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；苯、甲苯、二甲苯、氯苯等芳香族烴類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；乙腈、丙腈等腈類；N,N-二甲基甲醯胺、N,N-二 甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮等非質子性極性溶劑類；二***、環戊基甲醚、四氫呋喃、2-甲基四氫呋喃、1,4-二

Figure 108129126-A0202-12-0141-169
烷等醚類；水或此等混合溶劑等。此外，相對於化合物[II-2]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至10公升。 Examples of solvents that can be used in this step include: dichloromethane, chloroform, 1,2-dichloroethane and other halogenated hydrocarbons; benzene, toluene, xylene, chlorobenzene and other aromatic hydrocarbons; pentane and hexane , Cyclohexane, heptane and other aliphatic hydrocarbons; acetonitrile, propionitrile and other nitriles; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2- Aprotic polar solvents such as pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyl Tetrahydrofuran, 1,4-di
Figure 108129126-A0202-12-0141-169
Ethers such as alkanes; water or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 100 liters, preferably 0.3 to 10 liters relative to 1 mole of the compound [II-2].

本步驟之反應溫度可選自從-20℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於0℃至80℃的範圍內進行。 The reaction temperature in this step can be selected from any temperature range from -20°C to the reflux temperature in the reaction system, and preferably can be performed in the range of 0°C to 80°C.

本步驟之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為1分鐘至48小時。 Although the reaction time in this step varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 1 minute to 48 hours.

反應結束後將反應混合物注加於水中並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[I-19]。單離出之化合物[I-19]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water and extracted with an organic solvent, followed by concentration and other operations, whereby the compound [I-19] can be isolated. The single isolated compound [I-19] can be further purified by column chromatography, recrystallization, etc. as required.

〈製造方法14〉 <Manufacturing method 14>

本發明之化合物中，通式[I]所表示之化合物例如可使用通式[I-20]所表示之化合物並依循由下述所例示之反應式所組成之方法來製造。 Among the compounds of the present invention, the compound represented by the general formula [I] can be produced, for example, using the compound represented by the general formula [I-20] and following the method composed of the reaction formula exemplified below.

Figure 108129126-A0202-12-0141-36
Figure 108129126-A0202-12-0141-36

(式中，A、R1、R2、R3、R4、R5、R6及n表示與前述相同意義，L8表示鹵素原子、甲烷磺醯基氧基、三氟甲烷磺醯基氧基、九氟丁烷磺醯基氧基、苯磺醯基氧基或對甲苯磺醯基氧基等) (In the formula, A, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n represent the same meaning as above, L 8 represents a halogen atom, methanesulfonyloxy, trifluoromethanesulfonyl Oxy, nonafluorobutanesulfonyloxy, benzenesulfonyloxy or p-toluenesulfonyloxy, etc.)

亦即，通式[I]所表示之本發明之化合物可藉由在適當之鹼的存在下或不存在下，於適當的溶劑中使通式[I-20]所表示之化合物與化合物[IV-19]進行反應而製造。 That is, the compound of the present invention represented by the general formula [I] can be prepared by using the compound represented by the general formula [I-20] and the compound [in the presence or absence of an appropriate base in an appropriate solvent IV-19] Manufactured by reaction.

相對於化合物[I-20]1莫耳，本反應中所使用之化合物[IV-19]的使用量可適當地選自1至100莫耳的範圍，較佳為1.0至10.0莫耳。 The amount of the compound [IV-19] used in this reaction can be appropriately selected from the range of 1 to 100 moles relative to 1 mole of the compound [I-20], preferably 1.0 to 10.0 moles.

於本反應中使用鹼時，能夠使用之鹼可列舉例如：氫氧化鈉、氫氧化鉀、氫氧化鋰等鹼金屬的氫氧化物類；氫氧化鈣、氫氧化鎂等鹼土類金屬的氫氧化物類；碳酸鈉、碳酸鉀等鹼金屬的碳酸鹽類；碳酸氫鈉、碳酸氫鉀等鹼金屬的重碳酸鹽類等無機鹼類；氫化鈉、氫化鉀等金屬氫化物類；甲氧化鈉、乙氧化鈉、第三丁氧化鉀等醇的金屬鹽類或三乙胺、N,N-二甲基苯胺、吡啶、4-N,N-二甲基胺基吡啶、1,8-二氮雜雙環[5,4,0]-7-十一烯等有機鹼類等。此外，相對於化合物[I-20]1莫耳，鹼的使用量可適當地選自1至10莫耳的範圍，較佳為1.0至5.0莫耳。 When an alkali is used in this reaction, the alkali that can be used includes, for example, hydroxides of alkali metals such as sodium hydroxide, potassium hydroxide, and lithium hydroxide; hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide Species; carbonates of alkali metals such as sodium carbonate and potassium carbonate; inorganic bases such as bicarbonates of alkali metals such as sodium bicarbonate and potassium bicarbonate; metal hydrides such as sodium hydride and potassium hydride; sodium methoxide , Sodium ethoxide, potassium tributoxide and other metal salts of alcohol or triethylamine, N,N-dimethylaniline, pyridine, 4-N,N-dimethylaminopyridine, 1,8-di Organic bases such as azabicyclo[5,4,0]-7-undecene. In addition, the amount of the base used can be appropriately selected from the range of 1 to 10 mols relative to 1 mol of the compound [I-20], preferably 1.0 to 5.0 mols.

本反應中能夠使用之溶劑可列舉例如：二***、環戊基甲醚、四氫呋喃、2-甲基四氫呋喃、1,4-二

Figure 108129126-A0202-12-0142-170
烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；乙酸乙酯等酯類；乙腈、丙腈等腈類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇等醇類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；丙酮、丁酮、環己酮等酮類或此等混合溶劑等。相對於化合物[I-20]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至20公升。 Examples of solvents that can be used in this reaction include: diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-bis
Figure 108129126-A0202-12-0142-170
Ethers such as alkane; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; esters such as ethyl acetate; nitriles such as acetonitrile and propionitrile; N,N-dimethylformamide, N,N- Aprotic polar solvents such as dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; methanol , Ethanol, 2-propanol and other alcohols; dichloromethane, chloroform, 1,2-dichloroethane and other halogenated hydrocarbons; pentane, hexane, cyclohexane, heptane and other aliphatic hydrocarbons; acetone, Ketones such as butanone and cyclohexanone or these mixed solvents. The use amount of the solvent is 0.1 to 100 liters, preferably 0.3 to 20 liters relative to 1 mole of the compound [I-20].

本反應之反應溫度可選自從-20℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於-10℃至80℃的範圍內進行。 The reaction temperature of the present reaction can be selected from any temperature range from -20°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of -10°C to 80°C.

本反應之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為15分鐘至48小時。 Although the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 15 minutes to 48 hours.

反應結束後將反應混合物注加於水中並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[I]。單離出之化合物[I]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water and extracted with an organic solvent, followed by concentration and other operations, whereby compound [I] can be isolated. The isolated compound [I] can be further purified by column chromatography, recrystallization, etc. as required.

〈製造方法15〉 <Manufacturing method 15>

本發明之化合物中，通式[I-21]所表示之化合物例如可使用通式[I-19]所表示之化合物並依循由下述所例示之反應式所組成之方法來製造。 Among the compounds of the present invention, the compound represented by the general formula [I-21] can be produced, for example, using the compound represented by the general formula [I-19] and following the method composed of the reaction formula exemplified below.

Figure 108129126-A0202-12-0143-37
Figure 108129126-A0202-12-0143-37

(式中，R1、R2、R3、R4、R5、R6及n表示與前述相同意義) (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n represent the same meaning as above)

亦即，通式[I-21]所表示之化合物可藉由在適當之鹼的存在下或不存在下，於適當之溶劑的存在下或不存在下，使通式[I-19]所表示之化合物與適當的硫羰化劑進行反應而製造。 That is, the compound represented by the general formula [I-21] can be represented by the general formula [I-19] in the presence or absence of an appropriate base, in the presence or absence of an appropriate solvent The compound represented is produced by reacting with an appropriate thiocarbonylating agent.

本反應中所使用之硫羰化劑可列舉出五硫化二磷或勞森試劑(Lawesson's Reagent，2,4-雙(4-甲氧基苯基)-1,3,2,4-二噻二磷雜丁環-2,4-二硫化物)等。此外，相對於化合物[I-19]1莫耳，硫羰化劑的使用量可適當地選自0.5至100莫耳的範圍，較佳為0.5至3.0莫耳。 The thiocarbonylating agent used in this reaction may include phosphorus pentasulfide or Lawesson's Reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphospha Butadiene-2,4-disulfide) etc. In addition, the use amount of the thiocarbonylating agent can be appropriately selected from the range of 0.5 to 100 moles relative to 1 mole of the compound [I-19], preferably 0.5 to 3.0 moles.

於本反應中鹼的添加並非必須，惟在使用鹼時，能夠使用之鹼可列舉例如：碳酸鈉、碳酸鉀等鹼金屬的碳酸鹽類等無機鹼類或三乙胺、N,N-二甲基苯胺、吡啶、4-N,N-二甲基胺基吡啶、1,8-二氮雜雙環[5,4,0]-7-十一烯等有機鹼類等。此外，相對於化合物[I-19]1莫耳，鹼的使用量可適當地選自0.01至10莫耳的範圍，較佳為0.1至2.0莫耳。 It is not necessary to add a base in this reaction, but when using a base, the base that can be used includes, for example, inorganic bases such as alkali metal carbonates such as sodium carbonate and potassium carbonate or triethylamine, N,N-di Organic bases such as toluidine, pyridine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5,4,0]-7-undecene, etc. In addition, the amount of the base used can be appropriately selected from the range of 0.01 to 10 moles relative to 1 mole of compound [I-19], preferably 0.1 to 2.0 moles.

本反應中能夠使用之溶劑可列舉例如：二***、環戊基甲醚、四氫呋喃、2-甲基四氫呋喃、1,4-二

Figure 108129126-A0202-12-0144-171
烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；二甲基亞碸、環丁碸等非質子性極性溶劑類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；戊烷、己烷、環己烷、庚烷等脂肪族烴類或此等混合溶劑等。此外，相對於化合物[I-19]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至15公升。 Examples of solvents that can be used in this reaction include: diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-bis
Figure 108129126-A0202-12-0144-171
Ethers such as alkanes; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aprotic polar solvents such as dimethyl sulfoxide and cyclobutane; dichloromethane, chloroform, 1,2-dichloroethane Halogenated hydrocarbons such as alkanes; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane, or these mixed solvents; In addition, the amount of the solvent used is 0.1 to 100 liters, preferably 0.3 to 15 liters relative to 1 mole of the compound [I-19].

本反應之反應溫度可選自從0℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於0℃至150℃的範圍內進行。 The reaction temperature of this reaction can be selected from any temperature range from 0°C to the reflux temperature in the reaction system, and it is preferably carried out in the range of 0°C to 150°C.

本反應之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為15分鐘至48小時。 Although the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 15 minutes to 48 hours.

反應結束後將反應混合物注加於水中並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[I-19]。單離出之化合物[I-19]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water and extracted with an organic solvent, followed by concentration and other operations, whereby the compound [I-19] can be isolated. The single isolated compound [I-19] can be further purified by column chromatography, recrystallization, etc. as required.

〈中間物的製造方法1〉 <Method of Manufacturing Intermediate 1>

通式[III-3]所表示之化合物例如可使用通式[III-7]所表示之化合物並依循由下述所例示之反應式所組成之方法來製造。 The compound represented by the general formula [III-3] can be produced, for example, using the compound represented by the general formula [III-7] and following the method composed of the reaction formula exemplified below.

Figure 108129126-A0202-12-0145-38
Figure 108129126-A0202-12-0145-38

(式中，R3、R4、Ra及n表示與前述相同意義) (Wherein, R 3, R 4, R a and n represent the same meaning as aforementioned)

(步驟1’-1) (Step 1’-1)

亦即，通式[III-8]所表示之化合物可依據實驗化學講座第4版(丸善)、第26卷之「還原一般的項目」，藉由還原通式[III-7]所表示之硝基化合物而製造。 That is, the compound represented by the general formula [III-8] can be expressed by reducing the general formula [III-7] according to the "General Items of Reduction" in the fourth edition of the Lecture on Experimental Chemistry (Maruzen), Volume 26 Nitro compounds.

化合物[III-7]可使用一般所能夠取得之試劑，再者，亦可依據國際公開專利公報WO2009/078481號所記載之方法或其方法來製造。 Compound [III-7] can be obtained using generally available reagents, or it can be produced according to the method described in International Publication Patent Publication WO2009/078481 or its method.

(步驟1’-2) (Step 1’-2)

通式[III-3]所表示之化合物可藉由在適當之無機酸的存在下，於適當的溶劑中使通式[III-8]所表示之化合物與亞硝酸鹽進行反應形成重氮鹽後，藉由鋅粉末、亞硫酸鈉、氯化錫等金屬還原試劑將此還原而製造。 The compound represented by the general formula [III-3] can form a diazonium salt by reacting the compound represented by the general formula [III-8] with a nitrite in an appropriate solvent in the presence of a suitable inorganic acid After that, it is produced by reducing this with a metal reducing agent such as zinc powder, sodium sulfite, and tin chloride.

本步驟中能夠使用之無機酸可列舉出鹽酸、硫酸等。此外，相對於化合物[III-8]1莫耳，無機酸的使用量可適當地選自2至10莫耳的範圍，較佳為2.0至5.0莫耳。 Examples of inorganic acids that can be used in this step include hydrochloric acid and sulfuric acid. In addition, the amount of the inorganic acid used can be appropriately selected from the range of 2 to 10 moles relative to 1 mole of the compound [III-8], preferably 2.0 to 5.0 moles.

相對於化合物[III-8]1莫耳，本步驟中所使用之亞硝酸鹽的使用量可適當地選自1至5莫耳的範圍，較佳為1.0至1.2莫耳。 The amount of nitrite used in this step can be appropriately selected from the range of 1 to 5 moles relative to 1 mole of compound [III-8], preferably 1.0 to 1.2 moles.

相對於化合物[III-8]1莫耳，本步驟中能夠使用之金屬還原試劑的使用量可適當地選自1至20莫耳的範圍，較佳為1.0至5.0莫耳。 The amount of the metal reducing agent that can be used in this step can be appropriately selected from the range of 1 to 20 moles, preferably 1.0 to 5.0 moles relative to 1 mole of compound [III-8].

本步驟中能夠使用之溶劑可列舉例如：水、鹽酸、硫酸、乙酸或此等混合溶劑等。此外，相對於化合物[III-8]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至10公升。 Examples of the solvent that can be used in this step include water, hydrochloric acid, sulfuric acid, acetic acid, and mixed solvents of these. In addition, the amount of the solvent used is 0.1 to 100 liters relative to 1 mole of compound [III-8], preferably 0.3 to 10 liters.

本步驟之反應溫度可選自從-20℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於-5℃至20℃的範圍內進行。 The reaction temperature in this step can be selected from any temperature range from -20°C to the reflux temperature in the reaction system, and is preferably performed in the range of -5°C to 20°C.

本步驟之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為30分鐘至5小時。 Although the reaction time in this step varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 30 minutes to 5 hours.

反應結束後將反應混合物注加於水中並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[III-3]。單離出之化合物[III-3]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction, the reaction mixture is poured into water and extracted with an organic solvent, followed by concentration, etc., whereby the compound [III-3] can be isolated. The isolated compound [III-3] can be further purified by column chromatography, recrystallization, etc. as required.

〈中間物的製造方法2〉 <Manufacturing method of intermediate 2>

通式[III-1]所表示之化合物例如可使用通式[III-3]所表示之化合物並依循由下述所例示之反應式所組成之方法來製造。 The compound represented by the general formula [III-1] can be produced, for example, using the compound represented by the general formula [III-3] and following the method composed of the reaction formula exemplified below.

Figure 108129126-A0202-12-0146-40
Figure 108129126-A0202-12-0146-40

(式中，R3、R4、R5、R6、Ra、Rb、L1、L3及n表示與前述相同意義) (Wherein, R 3, R 4, R 5, R 6, R a, R b, L 1, L 3 and n are the same meaning as aforementioned)

(步驟2’-1) (Step 2’-1)

亦即，通式[III-1]所表示之化合物可藉由在適當之酸觸媒的存在下或不存在下，於適當的溶劑中使通式[III-3]所表示之化合物與化合物[IV-20]或化合物[IV-21]進行反應而形成通式[III-9]所表示之化合物後，藉由鹵化劑進行反應而製造。 That is, the compound represented by the general formula [III-1] can be prepared by using the compound represented by the general formula [III-3] and the compound in the presence or absence of an appropriate acid catalyst in an appropriate solvent After [IV-20] or compound [IV-21] is reacted to form the compound represented by general formula [III-9], it is produced by reacting with a halogenating agent.

相對於化合物[III-3]1莫耳，本步驟中所使用之化合物[IV-20]或化合物[IV-21]的使用量可適當地選自1至5莫耳的範圍，較佳為1.0至1.2莫耳。 The amount of the compound [IV-20] or compound [IV-21] used in this step can be appropriately selected from the range of 1 to 5 moles relative to 1 mole of compound [III-3], preferably 1.0 to 1.2 mol.

本步驟中能夠使用之酸觸媒可列舉例如：甲烷磺酸或對甲苯磺酸等磺酸類；四氯化鈦等路易斯酸等。此外，相對於化合物[III-3]1莫耳，酸觸媒的使用量可適當地選自0.001至5莫耳的範圍，較佳為0.01至1.2莫耳。 Examples of acid catalysts that can be used in this step include methanesulfonic acid and p-toluenesulfonic acid, and other Lewis acids such as titanium tetrachloride. In addition, the amount of the acid catalyst used can be appropriately selected from the range of 0.001 to 5 mols relative to 1 mol of the compound [III-3], preferably 0.01 to 1.2 mols.

本步驟中能夠使用之溶劑可列舉例如：二***、環戊基甲醚、四氫呋喃、2-甲基四氫呋喃、1,4-二

Figure 108129126-A0202-12-0147-172
烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；乙腈、丙腈等腈類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇、異丙醇等醇類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；吡啶、甲吡啶等吡啶類或此等混合溶劑等。此外，相對於化合物[III-3]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至10公升。 Examples of solvents that can be used in this step include: diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-bis
Figure 108129126-A0202-12-0147-172
Ethers such as alkanes; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile and propionitrile; N,N-dimethylformamide, N,N-dimethylacetamide, Aprotic polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; methanol, ethanol, 2-propanol , Alcohols such as isopropyl alcohol; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane; pyridines such as pyridine and picoline or mixed solvents of these. In addition, the amount of the solvent used is 0.1 to 100 liters, preferably 0.3 to 10 liters relative to 1 mole of the compound [III-3].

本步驟中所使用之鹵化劑可列舉例如：氯、N-氯琥珀醯亞胺、N-溴琥珀醯亞胺、次氯酸第三丁酯等。此外，相對於化合物[III-9]1莫耳，鹵化劑的使用量可適當地選自1至5莫耳的範圍，較佳為1.0至1.1莫耳。 Examples of the halogenating agent used in this step include chlorine, N-chlorosuccinimide, N-bromosuccinimide, and tertiary butyl hypochlorite. In addition, the use amount of the halogenating agent can be appropriately selected from the range of 1 to 5 moles relative to 1 mole of the compound [III-9], preferably 1.0 to 1.1 moles.

本步驟之反應溫度可選自從-70℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於-20℃至100℃的範圍內進行。 The reaction temperature in this step can be selected from any temperature range from -70°C to the reflux temperature in the reaction system, and preferably can be performed in the range of -20°C to 100°C.

本步驟之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為15分鐘至24小時。 Although the reaction time in this step varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 15 minutes to 24 hours.

反應結束後將反應混合物注加於水中並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[III-1]。單離出之化合物[III-1]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water and extracted with an organic solvent, followed by concentration, etc., whereby the compound [III-1] can be isolated. The isolated compound [III-1] can be further purified by column chromatography, recrystallization, etc. as required.

(步驟2’-2) (Step 2’-2)

再者，通式[III-1]所表示之化合物可藉由在適當之鹼的存在下或不存在下，於適當的溶劑中使通式[III-3]所表示之化合物與化合物[IV-22]進行反應而形成通式[III-10]所表示之化合物後，藉由鹵化劑進行反應而製造。 Furthermore, the compound represented by the general formula [III-1] can be prepared by using the compound represented by the general formula [III-3] and the compound [IV in the presence or absence of an appropriate base in an appropriate solvent -22] After the reaction to form the compound represented by the general formula [III-10], it is produced by reacting with a halogenating agent.

相對於化合物[III-3]1莫耳，本步驟中所使用之化合物[IV-22]的使用量可適當地選自1至15莫耳的範圍，較佳為1.0至7.0莫耳。 The use amount of the compound [IV-22] used in this step can be appropriately selected from the range of 1 to 15 moles relative to 1 mole of compound [III-3], preferably 1.0 to 7.0 moles.

本步驟中能夠使用之鹼可列舉例如：氫氧化鈉、氫氧化鉀、氫氧化鋰等鹼金屬的氫氧化物類；氫氧化鈣、氫氧化鎂等鹼土類金屬的氫氧化物類；碳酸鈉、碳酸鉀等鹼金屬的碳酸鹽類；碳酸氫鈉、碳酸氫鉀等鹼金屬的重碳酸鹽類等無機鹼類；氫化鈉、氫化鉀等金屬氫化物類；甲氧化鈉、乙氧化鈉、第三丁氧化鉀等醇的金屬鹽類；或三乙胺、N,N-二甲基苯胺、吡啶、4-N,N-二甲基胺基吡啶、1,8-二氮雜雙環[5,4,0]-7-十一烯等有機鹼類等。此外，相對於化合物[III-3]1莫耳，鹼的使用量可適當地選自1至10莫耳的範圍，較佳為1.0至1.2莫耳。 Examples of the base that can be used in this step include: hydroxides of alkali metals such as sodium hydroxide, potassium hydroxide, and lithium hydroxide; hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide; sodium carbonate , Potassium carbonate and other alkali metal carbonates; sodium bicarbonate, potassium bicarbonate and other alkali metal bicarbonates and other inorganic bases; sodium hydride, potassium hydride and other metal hydrides; sodium methoxide, sodium ethoxide, Metal salts of alcohols such as potassium tributoxide; or triethylamine, N,N-dimethylaniline, pyridine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[ 5,4,0]-7-undecene and other organic bases. In addition, the amount of the base used can be appropriately selected from the range of 1 to 10 moles relative to 1 mole of compound [III-3], preferably 1.0 to 1.2 moles.

本步驟中能夠使用之溶劑可列舉例如：二***、環戊基甲醚、四氫呋喃、2-甲基四氫呋喃、1,4-二

Figure 108129126-A0202-12-0149-173
烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；乙腈、丙腈等腈類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇等醇類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；乙酸乙酯等酯類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；吡啶、甲吡啶等吡啶類或此等混合溶劑等。此外，相對於化合物[III-3]1莫耳，溶劑的使用量為0.1至100公升，較佳為0.3至10公升。 Examples of solvents that can be used in this step include: diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-bis
Figure 108129126-A0202-12-0149-173
Ethers such as alkanes; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile and propionitrile; N,N-dimethylformamide, N,N-dimethylacetamide, Aprotic polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; methanol, ethanol, 2-propanol Alcohols; dichloromethane, chloroform, 1,2-dichloroethane and other halogenated hydrocarbons; ethyl acetate and other esters; pentane, hexane, cyclohexane, heptane and other aliphatic hydrocarbons; pyridine, Pyridines such as picoline or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 100 liters, preferably 0.3 to 10 liters relative to 1 mole of the compound [III-3].

本步驟中能夠使用之鹵化劑可列舉例如：三氯化磷、三溴化磷、亞硫醯氯、氧基氯化磷、五氯化磷、三苯基膦/四氯化碳或三苯基膦/四溴化碳等。此外，相對於化合物[III-10]1莫耳，鹵化劑的使用量可適當地選自從1莫耳至相當於溶劑量的範圍，較佳為1.0至5.0莫耳。 Examples of the halogenating agent that can be used in this step include: phosphorus trichloride, phosphorus tribromide, thionyl chloride, phosphorus oxychloride, phosphorus pentachloride, triphenylphosphine/carbon tetrachloride, or tribenzene Phosphine/carbon tetrabromide, etc. In addition, the use amount of the halogenating agent can be appropriately selected from the range of 1 mole to the equivalent amount of the solvent relative to 1 mole of the compound [III-10], preferably 1.0 to 5.0 moles.

本步驟之反應溫度可選自從-70℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於-20℃至100℃的範圍內進行。 The reaction temperature in this step can be selected from any temperature range from -70°C to the reflux temperature in the reaction system, and preferably can be performed in the range of -20°C to 100°C.

本步驟之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為15分鐘至24小時。 Although the reaction time in this step varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 15 minutes to 24 hours.

反應結束後將反應混合物注加於水中並利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[III-1]。或者是，亦可藉由從反應混合物中將溶劑濃縮而單離出化合物[III-1]。單離出之化合物[III-1]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water and extracted with an organic solvent, followed by concentration, etc., whereby the compound [III-1] can be isolated. Alternatively, the compound [III-1] can also be isolated by concentrating the solvent from the reaction mixture. The isolated compound [III-1] can be further purified by column chromatography, recrystallization, etc. as required.

〈中間物的製造方法3〉 <Manufacturing method of intermediate 3>

通式[III-5]所表示之化合物例如可使用通式[III-11]所表示之化合物並依循由下述所例示之反應式所組成之方法來製造。 The compound represented by the general formula [III-5] can be produced, for example, using the compound represented by the general formula [III-11] and following the method composed of the reaction formula exemplified below.

Figure 108129126-A0202-12-0150-41
Figure 108129126-A0202-12-0150-41

(式中，R3、R4、R5、R6、X及n表示與前述相同意義) (In the formula, R 3 , R 4 , R 5 , R 6 , X and n represent the same meaning as above)

亦即，通式[III-5]所表示之化合物可藉由在適當的溶劑中使通式[III-11]所表示之化合物與鹵化劑進行反應而製造。 That is, the compound represented by the general formula [III-5] can be produced by reacting the compound represented by the general formula [III-11] with a halogenating agent in an appropriate solvent.

本反應中能夠使用之鹵化劑可列舉出：氯、氯化磺醯、N-氯琥珀醯亞胺、溴、N-溴琥珀醯亞胺、1,3-二溴-5,5-乙內醯脲、碘、N-碘琥珀醯亞胺、1,3-二碘-5,5-乙內醯脲等。此外，相對於化合物[III-11]1莫耳，鹵化劑的使用量可適當地選自0.5至10莫耳的範圍，較佳為0.5至2.0莫耳。 Examples of halogenating agents that can be used in this reaction include: chlorine, sulfonamide chloride, N-chlorosuccinimide, bromine, N-bromosuccinimide, 1,3-dibromo-5,5-acetone Acetyl urea, iodine, N-iodosuccinimide, 1,3-diiodo-5,5-hydantoin, etc. In addition, the use amount of the halogenating agent can be appropriately selected from the range of 0.5 to 10 moles, preferably 0.5 to 2.0 moles relative to 1 mole of the compound [III-11].

本反應中能夠使用之溶劑可列舉例如：二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；乙腈、丙腈等腈類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮等非質子性極性溶劑類；乙酸、丙酸、三氟乙酸等羧酸類；硫酸、水、或此等混合溶劑等。此外，相對於化合物[III-11]1莫耳，溶劑的使用量為0.1至300公升，較佳為0.3至20公升。 Examples of solvents that can be used in this reaction include halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; acetonitrile, Nitriles such as propionitrile; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1 , 3-dimethyl-2-imidazolidinone and other aprotic polar solvents; carboxylic acids such as acetic acid, propionic acid, trifluoroacetic acid; sulfuric acid, water, or mixed solvents of these. In addition, the amount of the solvent used is 0.1 to 300 liters relative to 1 mole of the compound [III-11], preferably 0.3 to 20 liters.

本反應之反應溫度通常可選自從-70℃至反應系統中的迴流溫度為止之任意的溫度範圍，較佳可於-20℃至100℃的範圍內進行。 The reaction temperature of this reaction can be generally selected from any temperature range from -70°C to the reflux temperature in the reaction system, and is preferably carried out in the range of -20°C to 100°C.

本反應之反應時間雖因反應溫度、反應基質、反應量等而有所不同，但通常為10分鐘至24小時。 Although the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., it is usually 10 minutes to 24 hours.

反應結束後將反應混合物注加於水中，濾取所析出之固體或利用有機溶劑萃取後進行濃縮等操作，藉此可單離出化合物[III-5]。單離出之化合物[III-5]可因應所需藉由管柱層析、再結晶等進行進一步精製。 After the reaction is completed, the reaction mixture is poured into water, and the precipitated solid is filtered out or extracted with an organic solvent and then concentrated, and the compound [III-5] can be isolated. The isolated compound [III-5] can be further purified by column chromatography, recrystallization, etc. as required.

本發明之通式[II]所表示之3-(1H-1,2,4-***-1-基)苯甲酸衍生物或其酯體，係有用於作為在製造本發明之通式[I]所表示之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物或其農業上可容許之鹽時之中間物的化合物。 The 3-(1H-1,2,4-triazol-1-yl)benzoic acid derivative represented by the general formula [II] of the present invention or its ester body is useful as a general formula for producing the present invention [ I] The compound represented by 3-(1H-1,2,4-triazol-1-yl)benzamide derivative or its agriculturally acceptable salt represented by the intermediate.

再者，本發明之通式[III]所表示之1-苯基-1H-1,2,4-***衍生物，係有用於作為在製造本發明之通式[II]所表示之3-(1H-1,2,4-***-1-基)苯甲酸衍生物或其酯體時之中間物的化合物。 Furthermore, the 1-phenyl-1H-1,2,4-triazole derivative represented by the general formula [III] of the present invention is useful for the production of the general formula [II] represented by the present invention [3] -Intermediate compounds when (1H-1,2,4-triazol-1-yl)benzoic acid derivatives or their esters are used.

本發明之農藥組成物係含有本發明之通式[I]所表示之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物或其農業上可容許之鹽作為有效成分。 The pesticide composition of the present invention contains the 3-(1H-1,2,4-triazol-1-yl) benzamide derivative represented by the general formula [I] of the present invention or its agriculturally acceptable Salt as an active ingredient.

本發明之農藥組成物可因應所需含有通常被使用在農藥製劑之添加成分(載體)。 The pesticide composition of the present invention may contain additional components (carriers) that are usually used in pesticide preparations as needed.

本發明之有害生物防除劑係含有本發明之通式[I]所表示之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物或其農業上可容許之鹽作為有效成分。本發明之有害生物防除劑具代表性者為殺蟲劑、殺蟎劑及殺線蟲劑。 The pest control agent of the present invention contains the 3-(1H-1,2,4-triazol-1-yl) benzamide derivative represented by the general formula [I] of the present invention or its agriculturally acceptable The salt as an active ingredient. The representative pest control agents of the present invention are insecticides, acaricides and nematicides.

本發明的有害生物防除劑係因應所需可含有在農藥製劑通常被使用的添加成分(載體)。 The pest control agent of the present invention may contain additional components (carriers) that are usually used in pesticide preparations as needed.

該添加成分可舉：固體載體或液體載體等載體、界面活性劑、結合劑及賦黏劑、增黏劑、著色劑、擴展劑、展著劑、抗凍劑、抗結塊劑、崩解劑、抗分解劑等，因應其他所需時，也可使用防腐劑及植物片等作為添加成分。再者，此等添加成分是可以使用1種，再者，也可以將2種以上組合使用。 Examples of the added component include carriers such as solid carriers or liquid carriers, surfactants, binders and tackifiers, tackifiers, colorants, extenders, spreading agents, antifreeze agents, anti-caking agents, and disintegration Agents, anti-decomposition agents, etc., according to other needs, preservatives and plant tablets can also be used as additional ingredients. In addition, one type of these additional components may be used, or two or more types may be used in combination.

以下，詳細地說明上述添加成分。 Hereinafter, the above-mentioned added components will be described in detail.

固體載體例如可舉：葉蠟石黏土、高嶺黏土、矽石黏土、滑石、矽藻土、沸石、皂土、酸性白土、活性白土、鎂鋁海泡石(attapulgite)黏土、蛭石、珍珠岩、浮石、白碳(合成矽酸、合成矽酸鹽等)、二氧化鈦等礦物系載體；木質粉、玉米莖、核桃殼、果實核、稻殼、鋸木屑、麩皮、大豆粉、粉末纖維素、澱粉、糊精、糖類等植物性載體；碳酸鈣、硫酸銨、硫酸鈉、氯化鉀等無機鹽類載體；聚乙烯、聚丙烯、聚氯乙烯、聚乙酸乙烯酯、乙烯-乙酸乙烯酯共聚物、尿素-醛樹脂等高分子載體等。 Examples of solid carriers include pyrophyllite clay, kaolin clay, silica clay, talc, diatomaceous earth, zeolite, bentonite, acid clay, activated clay, attapulgite clay, vermiculite, and perlite , Pumice, white carbon (synthetic silicic acid, synthetic silicate, etc.), titanium dioxide and other mineral-based carriers; wood flour, corn stalks, walnut shells, fruit kernels, rice husks, sawdust, bran, soy flour, powdered cellulose , Starch, dextrin, sugar and other vegetable carriers; calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride and other inorganic salt carriers; polyethylene, polypropylene, polyvinyl chloride, polyvinyl acetate, ethylene-vinyl acetate Polymer carriers such as copolymers and urea-aldehyde resins.

液體載體例如可舉：甲醇、乙醇、丙醇、2-丙醇、丁醇、環己醇等一元醇類；乙二醇、二乙二醇、丙二醇、己二醇、聚乙二醇、聚丙二醇、甘油等多元醇類；丙烯系二醇醚等多元醇衍生物類；丙酮、甲基乙基酮、甲基異丁基酮、二異丁基酮、環己酮、異佛酮等酮類；***、1,4-二

Figure 108129126-A0202-12-0152-174
烷、2-乙氧基乙醇(cellosolve)、二丙基醚、四氫呋喃等醚類；直鏈烷烴(normal paraffin)、環烷烴(naphthene)、異構烷烴(isoparaffin)、煤油、礦油等脂肪族烴類；甲苯、C9-C10烷基苯、二甲苯、溶劑石油腦(solvent naphtha)、烷基萘、高沸點芳香族烴等芳香族烴類；1,2-二氯乙烷、氯仿、四氯化碳等鹵化烴類；乙酸乙酯、苯二甲酸二異丙酯、苯二甲酸二丁酯、苯二甲酸二辛酯、己二酸二甲酯等酯類；γ-丁內酯之等內酯類；N,N-二甲基甲醯胺、N,N-二乙基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯酮等醯胺類；乙腈等腈類；二甲基亞碸等硫化合物類；大豆油、菜籽油、棉籽油、椰子油、蓖麻籽油等植物油；水等。 Examples of the liquid carrier include monohydric alcohols such as methanol, ethanol, propanol, 2-propanol, butanol, and cyclohexanol; ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, and polyethylene glycol. Polyols such as propylene glycol and glycerin; polyhydric alcohol derivatives such as propylene glycol ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, and isophorone Class; ether, 1,4-di
Figure 108129126-A0202-12-0152-174
Alkanes, 2-ethoxyethanol (cellosolve), dipropyl ether, tetrahydrofuran and other ethers; linear paraffins (normal paraffin), naphthene (naphthene), isoparaffin (isoparaffin), kerosene, mineral oil and other aliphatic Hydrocarbons; aromatic hydrocarbons such as toluene, C 9 -C 10 alkylbenzene, xylene, solvent naphtha, alkyl naphthalene, high-boiling aromatic hydrocarbons; 1,2-dichloroethane, chloroform , Halogenated hydrocarbons such as carbon tetrachloride; ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate and other esters; γ-butyrolene Lactones such as esters; N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, etc. Acetamides; nitriles such as acetonitrile; sulfur compounds such as dimethyl sulfoxide; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, coconut oil, castor seed oil; water, etc.

界面活性劑沒有特別的限制，佳者是在水中顯示凝膠化、或表現膨潤性者，例如可舉：山梨醇酐脂肪酸酯、聚氧乙烯山梨醇酐脂肪酸酯、蔗糖脂肪酸酯、聚氧乙烯脂肪酸酯、聚氧乙烯樹脂酸酯、聚氧乙烯脂肪酸二酯、聚氧乙烯烷基醚、聚氧乙烯烷基苯基醚、聚氧乙烯二烷基苯基醚、聚氧乙烯烷基苯基醚福馬林縮合物、聚氧乙烯聚氧丙烯崁段共聚物、烷基聚氧乙烯聚丙烯崁段共聚物醚、聚氧乙烯烷基胺、聚氧乙烯脂肪醯胺、聚氧乙烯脂肪酸雙苯基醚、聚伸烷基苄基苯基醚、聚氧伸烷基苯乙烯基苯基醚、乙炔二醇、聚氧伸烷基加成乙炔二醇、聚氧乙烯醚型聚矽氧、酯型聚矽氧、氟系界面活性劑、聚氧乙烯蓖麻籽油、聚氧乙烯硬化蓖麻籽油等非離子性界面活性劑；烷基硫酸鹽、聚氧乙烯烷基醚硫酸鹽、聚氧乙烯烷基苯基醚硫酸鹽、聚氧乙烯苯乙烯基苯基醚硫酸鹽、烷基苯磺酸鹽、木質素磺酸鹽、烷基磺基琥珀酸鹽、萘磺酸鹽、烷基萘磺酸鹽、萘磺酸的福馬林縮合物的鹽、烷基萘磺酸的福馬林縮合物的鹽、脂肪酸鹽、聚羧酸鹽、N-甲基-脂肪酸肌胺酸酯、樹脂酸鹽、聚氧乙烯烷基醚磷酸鹽、聚氧乙烯烷基苯基醚磷酸鹽等陰離子性界面活性劑；月桂基胺鹽酸鹽、硬脂基胺鹽酸鹽、油基胺鹽酸鹽、硬脂基胺乙酸鹽、硬脂基胺丙基胺乙酸鹽、氯化烷基 三甲基銨、烷基二甲基羥基氯苯胺等烷基胺鹽等的陽離子界面活性劑；二烷基二胺基乙基甜菜鹼、烷基二甲基苄基甜菜鹼等甜菜鹼型、二烷基胺基乙基甘胺酸、烷基二甲基苄基甘胺酸等胺基酸型等的兩性界面活性劑等。 The surfactant is not particularly limited, and the one that shows gelation or swelling in water is preferred, for example: sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, Polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene Alkylphenyl ether formalin condensate, polyoxyethylene polyoxypropylene segment copolymer, alkyl polyoxyethylene polypropylene segment copolymer ether, polyoxyethylene alkylamine, polyoxyethylene fatty amide, polyoxyethylene Ethylene fatty acid diphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene glycol, polyoxyalkylene addition acetylene glycol, polyoxyethylene ether type poly Non-ionic surfactants such as silicone, ester-type silicone, fluorine-based surfactants, polyoxyethylene castor seed oil, polyoxyethylene hardened castor seed oil; alkyl sulfates, polyoxyethylene alkyl ethers Sulfate, polyoxyethylene alkyl phenyl ether sulfate, polyoxyethylene styryl phenyl ether sulfate, alkyl benzene sulfonate, lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonic acid Salt, alkyl naphthalene sulfonate, formalin condensate of naphthalene sulfonic acid, formalin condensate of alkyl naphthalene sulfonate, fatty acid salt, polycarboxylate, N-methyl-fatty acid sarcosinate Ester, resin acid salt, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl phenyl ether phosphate and other anionic surfactants; laurylamine hydrochloride, stearylamine hydrochloride, oleylamine Hydrochloride, stearylamine acetate, stearylaminepropylamine acetate, alkyl chloride Cationic surfactants such as alkylamine salts such as trimethylammonium and alkyldimethylhydroxychloroaniline; betaine types such as dialkyldiaminoethyl betaine and alkyldimethylbenzyl betaine, Amphoteric surfactants such as amino acid types such as dialkylaminoethylglycine and alkyldimethylbenzylglycine etc.

鍵結劑及賦黏劑例如可舉：羧甲基纖維素及其鹽、糊精、水溶性澱粉、黃原膠、瓜爾膠、蔗糖，聚乙烯吡咯烷酮、***樹膠、聚乙烯醇、聚乙酸乙烯酯，聚丙烯酸鈉、平均分子量6000至20000的聚乙二醇、平均分子量10萬至500萬的聚環氧乙烷，天然磷脂質(例如，腦磷脂酸、卵磷脂等)等。 Examples of binding agents and tackifiers include carboxymethyl cellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, and polyacetic acid Vinyl esters, sodium polyacrylate, polyethylene glycol with an average molecular weight of 6,000 to 20,000, polyethylene oxide with an average molecular weight of 100,000 to 5 million, natural phospholipids (eg, cephalinic acid, lecithin, etc.), etc.

增黏劑例如可舉：黃原膠、瓜爾膠、羧甲基纖維素、聚乙烯吡咯烷酮、羧乙烯聚合物、丙烯酸系聚合物、澱粉衍生物、多糖類等水溶性高分子；如高純度皂土，白碳的無機微粉等。 Examples of the thickener include xanthan gum, guar gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch derivatives, polysaccharides, and other water-soluble polymers; such as high purity Bentonite, inorganic fine powder of white carbon, etc.

著色劑例如可舉：氧化鐵、氧化鈦、普魯士藍等無機顏料；茜素染料、偶氮染料、金屬酞花青染料等有機染料等。 Examples of the colorant include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue; organic dyes such as alizarin dye, azo dye, and metal phthalocyanine dye.

擴展劑例如可舉：聚矽氧系界面活性劑、纖維素粉末、糊精、加工澱粉、聚胺基羧酸螯合物化合物、交聯聚乙烯基吡咯烷酮、順丁烯二酸及苯乙烯類、甲基丙烯酸共聚物、多元醇的聚合物與二甲酸酐的半酯、聚苯乙烯磺酸的水溶性鹽等。 Examples of the extender include polysiloxane-based surfactants, cellulose powder, dextrin, processed starch, polyaminocarboxylic acid chelate compounds, cross-linked polyvinylpyrrolidone, maleic acid, and styrenes. , Methacrylic acid copolymers, polyhydric alcohol polymers and half esters of dicarboxylic anhydride, water-soluble salts of polystyrene sulfonic acid, etc.

展著劑例如可舉：二烷基磺基琥珀酸鈉、聚氧乙烯烷基醚、聚氧乙烯烷基苯基醚、聚氧乙烯脂肪酸酯等各種界面活性劑；石蠟、萜烯、聚醯胺樹脂、聚丙烯酸鹽、聚氧乙烯、蠟、聚乙烯基烷基醚、烷基酚福馬林縮合物、合成樹脂乳液等。 Examples of the spreading agent include various surfactants such as sodium dialkylsulfosuccinate, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene fatty acid ester; paraffin, terpene, poly Acetamide resin, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ether, alkylphenol formalin condensate, synthetic resin emulsion, etc.

抗凍劑例如可舉：乙二醇、二乙二醇、丙二醇、甘油等多元醇類等。 Examples of antifreeze agents include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

抗結塊劑例如可舉：澱粉、海藻酸、甘露糖、半乳糖等多糖類；聚乙烯吡咯烷酮、白碳、酯膠、石油樹脂等。 Examples of anti-caking agents include polysaccharides such as starch, alginic acid, mannose, and galactose; polyvinylpyrrolidone, white carbon, ester gum, petroleum resin, and the like.

崩解劑例如可舉：三聚磷酸鈉、六偏磷酸鈉、硬脂酸金屬鹽、纖維素粉末、糊精、甲基丙烯酸酯的共聚物、聚乙烯吡咯烷酮、聚胺基羧酸螯合物化合物、磺化苯乙烯/異丁烯/順丁烯二酸酐共聚物、澱粉/聚丙烯腈接枝共聚物等。 Examples of the disintegrant include sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylate copolymer, polyvinylpyrrolidone, and polyaminocarboxylic acid chelate. Compounds, sulfonated styrene/isobutylene/maleic anhydride copolymer, starch/polyacrylonitrile graft copolymer, etc.

抗分解劑例如可舉：沸石、生石灰、氧化鎂等乾燥劑；酚系、胺系、硫系、磷酸系等抗氧化劑；水楊酸系、二苯基酮系等紫外線吸收劑等。 Examples of the anti-decomposition agent include desiccants such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenol-based, amine-based, sulfur-based, and phosphoric acid-based; ultraviolet absorbers such as salicylic acid-based and diphenyl ketone-based.

另一方面，本發明的有害生物防除劑中，含有上述添加成分時，關於其添加比率是以質量基準，在固體載體或液體載體等載體通常是在5至95%，佳者是20至90%的範圍選用，界面活性劑通常是在0.1%至30%，佳者是0.5至10%的範圍選用，其他添加劑是在0.1至30%，佳者是0.5至10%的範圍選用。 On the other hand, when the pest control agent of the present invention contains the above-mentioned added components, the addition ratio thereof is based on mass, and it is usually 5 to 95% in a solid carrier or liquid carrier, preferably 20 to 90 It is selected in the range of %, and the surfactant is usually selected in the range of 0.1% to 30%, preferably in the range of 0.5 to 10%, and other additives are selected in the range of 0.1 to 30%, preferably in the range of 0.5 to 10%.

本發明的有害生物防除劑是製劑化成下列任意劑型的製劑使用：粉劑、粉粒劑、粒劑、水和劑、水溶劑、顆粒水和劑、錠劑、轉移(jumper agent)劑、乳劑、油劑、液劑、懸浮劑(flowable agent)、乳化劑、微乳化劑、懸浮乳劑(Suspoemulsion)、微量散布劑、微膠囊劑、薰蒸劑、煙霧劑、誘餌劑、膏狀製劑等。 The pest control agent of the present invention is a preparation formulated into any of the following dosage forms: powder, powder granule, granule, water and agent, water solvent, granular water and agent, lozenge, jumper agent, emulsion, Oils, liquids, flowable agents, emulsifiers, microemulsifiers, suspension emulsions (Suspoemulsion), micro-dispersants, microcapsules, fumigants, aerosols, bait agents, paste preparations, etc.

此等製劑在實際的使用時，可直接使用，或者是以水等烯釋劑烯釋成預定濃度使用。含有本發明的化合物之各種製劑或其烯釋物的施用係以通常一般所行之施用方法，亦即，以散布(例如，噴霧、霧化、微粒化、散粉、散粒、水面施用、箱施用等)、土壤施用(例如，混入、灌注等)、表面施用(例如，塗布、粉衣、被覆等)、種子處理(例如，塗抹、粉衣處理等)、浸漬、毒餌、薰蒸施用等施用。再者，也可將前述有效成分在飼料中混合而給予家畜，兒防除在其***物中的有害蟲，特別是有害昆蟲的產生、成長。 When these preparations are actually used, they can be used directly, or they can be released to a predetermined concentration with a release agent such as water. The application of various preparations containing the compound of the present invention or its alkenes is by the usual general application method, that is, by spraying (for example, spraying, atomizing, micronizing, loose powder, loose granules, water surface application, tank Application, etc.), soil application (eg, mixing, infusion, etc.), surface application (eg, coating, powder coating, coating, etc.), seed treatment (eg, painting, powder coating treatment, etc.), dipping, poison bait, fumigation application, etc. Apply. In addition, the aforementioned active ingredients may be mixed in feed and given to livestock to prevent harmful insects in their excrement, especially the generation and growth of harmful insects.

本發明的有害生物的防除方法，係藉由在前述的施用方法中使用本發明的通式[I]表示的5-(1,2,4-***-5-基)苯甲醯胺衍生物或其在農業上可容許的鹽的有效成分量而實施。 The pest control method of the present invention is derived by using 5-(1,2,4-triazol-5-yl)benzamide represented by the general formula [I] of the present invention in the aforementioned application method The amount of the active ingredient of the substance or its agriculturally acceptable salt is implemented.

關於本發明的有害生物防除劑的有效成分的調配比率(質量%)可因應所需而適當地選擇。例如，製成粉劑、粉粒劑、微粒劑等時是在0.01至20%，佳者是0.05至10%的範圍適當地選擇為佳，製成粒劑等時是在0.1至30%，佳者是在0.5至20%的範圍適當地選擇為佳，製成水和劑、顆粒水和劑等時是在1至70%，佳者是在5至50%的範圍適當地選擇為佳，製成水溶劑、液劑等時是在1至95%，佳者是在10至80%的範圍適當地選擇為佳，製成乳劑等時是在5至90%，佳者是在10至80%的範圍適當地選擇為佳，製成油劑等時是在1至50%，佳者是在5至30%的範圍適當地選擇為佳，製成懸浮劑等時是在5至60%，佳者是在10至50%的範圍適當地選擇為佳，製成乳化劑、微乳化劑、懸浮乳劑等時是在5至70%，佳者是在10至60%的範圍適當地選擇為佳，製成錠劑、誘餌劑、膏 狀製劑等時在1至80%，佳者是在5至50%的範圍適當地選擇為佳，製成薰蒸劑等時在0.1至50%，佳者是在1至30%的範圍適當地選擇為佳，製成煙霧劑等時在0.05至20%，佳者是在0.1至10%的範圍適當地選擇為佳。 The compounding ratio (mass %) of the active ingredient of the pest control agent of the present invention can be appropriately selected according to needs. For example, when it is made into powders, granules, granules, etc., it is in the range of 0.01 to 20%, preferably in the range of 0.05 to 10%, and it is preferably selected in the range of 0.05 to 10%. It is preferably selected in the range of 0.5 to 20%, and it is preferably in the range of 1 to 70% when it is made into water and agent, granular water and agent, etc. It is preferably selected in the range of 5 to 50%. When it is made into water solvent, liquid agent, etc., it is in the range of 1 to 95%, preferably in the range of 10 to 80%. It is preferably selected in the range of 10 to 80%, and when it is made into emulsion, it is in the range of 5 to 90%, and the best is in the range of 10 to The range of 80% is preferably selected appropriately, when it is made into an oil agent, etc., it is 1 to 50%, and the case is preferably selected within a range of 5 to 30%, when it is made into a suspension agent, etc., it is 5 to 60. %, the better is appropriately selected in the range of 10 to 50%, preferably 5 to 70% when made into emulsifiers, microemulsifiers, suspending emulsions, etc., preferably in the range of 10 to 60% Choose better, make lozenges, baits, ointments The equivalent preparation is in the range of 1 to 80%, preferably in the range of 5 to 50%, preferably in the range of 0.1 to 50%, preferably in the range of 1 to 30%, when making the fumigant, etc. It is better to choose the place, when it is made into aerosol, etc., it is 0.05 to 20%, and the better is to choose it properly in the range of 0.1 to 10%.

此等製劑是烯釋成適當的濃度而散布或直接施用。 These formulations are released or applied directly to the appropriate concentration.

本發明的有害生物防除劑的施用係以烯釋劑烯釋使用時，通常以0.1至5000ppm的有效成分濃度進行。將製劑直接使用時的每單位面積的施用量，以有效成分化合物而言，每1ha使用0.1至5000g，惟，不限定於此等。 The application of the pest control agent of the present invention is usually carried out at an active ingredient concentration of 0.1 to 5000 ppm when it is used as a release agent. When the preparation is directly used, the application amount per unit area is 0.1 to 5000 g per 1ha for the active ingredient compound, but it is not limited thereto.

此外，本發明的有害生物防除劑不僅是將本發明的化合物單獨作為有效成分也充分有效，因應所需也可與其他肥料、農藥，例如，殺蟲劑、殺蟎劑、殺線蟲劑、增效劑、殺菌劑、抗病毒劑、誘引劑、除草劑、植物生長調整劑等混用、併用，此時也有表現更進一步優異的效果的情況。 In addition, the pest control agent of the present invention is not only effective when the compound of the present invention is used alone as an active ingredient, but can also be combined with other fertilizers and pesticides, such as insecticides, acaricides, nematicides, Effective agents, fungicides, antiviral agents, attractants, herbicides, plant growth regulators, etc. are mixed and used together, and in this case, even further excellent effects may be exhibited.

其次，例示可以混合或併用的公知殺蟲劑、殺蟎劑、殺線蟲劑、增效劑化合物。 Next, exemplified well-known insecticides, acaricides, nematicides, and synergist compounds that can be mixed or used together.

殺蟲活性成分： Insecticidal active ingredients:

阿納寧(acrinathrin)、印楝素(azadirachtin)、甲基吡啶磷(azamethiphos)、acynonapyr(通用名)、乙基谷速松(azinphos-ethyl)、甲基谷速松(azinphos-methyl)、亞醌蟎(acequinocyl)、亞滅培(acetamiprid)、乙醯蟲腈(acetoprole)、毆殺松(acephate)、亞環鍚(azocyclotin)、阿巴汀(abamectin)、雙丙環蟲酯(afidopyropen)、阿弗索拉納(afoxolaner)、磺胺蟎酯(amidoflumet)、三亞蟎(amitraz)、棉鈴威(alanycarb)、得滅克 (aldicarb)、涕滅威(aldoxycarb)、亞烈寧(allethrin)[包含d-順式-反式-體，d-反式-體]、依殺松(isazophos)、氯唑磷(isamidofos)、水胺硫磷(isocarbophos)、加福松(isoxathion)、isocycloseram(通用名)、甲基異柳磷(isofenphos-methyl)、滅必蝨(isoprocarb)、ε-甲氧苄氟菊酯單體(epsilon-metofluthrin)、ε-甲氧苄氟菊酯單體(epsilon-momfluorothrin)、伊維菌素(ivermectin)、滅線蟲松(imicyafos)、益達胺(imidacloprid)、依普寧(imiprothrin)、因得克(indoxacarb)、益化利(esfenvalerate)、愛芬克(ethiofencarb)、愛殺松(ethion)、益斯普(ethiprole)、二溴乙烯(ethylene dibromide)、依殺蟎(etoxazole)、依芬寧(etofenprox)、普伏松(ethoprophos)、益多松(etrimfos)、因滅汀(emamectin)、因滅汀(emamectin benzoate)、安殺番(endosulfan)、益避寧(empenthrin)、oxazosulfyl(通用名)、歐殺滅(oxamyl)、滅多松(oxydemeton-methyl)、異亞碸磷(oxydeprofos)、歐滅松(omethoate)、克線丹(cadusafos)、κ-七氟菊酯(κ-tefluthrin)、κ-畢芬寧(κ-bifenthrin)、水黃皮素(karanjin)、培丹(cartap)、加保利(carbaryl)、丁基加保扶(carbosulfan)、加保扶(carbofuran)、γ-BHC(gamma-BHC)、滅爾蝨(xylylcarb)、拜裕松(quinalphos)、烯蟲炔酯(kinoprene)、蟎離丹(chinomethionat)、蠅毒磷(coumaphos)、冰晶石(cryolite)、可尼丁(clothianidin)、克芬蟎(clofentezine)、可芬諾(chromafenozide)、剋安勃(chlorantraniliprole)、氯氧磷(chlorethoxyfos)、氯丹(chlordane)、氯化苦(chloropicrin)、陶斯松(chlorpyrifos)、甲基陶斯松(chlorpyrifos-methyl)、克凡派(chlorfenapyr)、氯芬松(chlorfenvinphos)、克福隆(chlorfluazuron)、氯甲磷(chlormephos)、右旋 反式氯丙炔菊酯(chloroprallethrin)、溴氰蟲醯胺(cyazypyr)、氰乃松(cyanophos)、汰芬隆(diafenthiuron)、除線特(diamidafos)、氰蟲醯胺(cyantraniliprole)、得氯蟎(dienochlor)、唑蟎氰(cyenopyrafen)、殺力松(dioxabenzofos)、苯蟲醚(diofenolan)、環溴蟲醯胺(cyclaniliprole)、環氧蟲啶(cycloxaprid)、雙特松(dicrotophos)、除線磷(dichlofenthion)、乙氰菊酯(cycloprothrin)、二氯松(dichlorvos)、dicloromezotiaz(通用名)、大克蟎(dicofol)、環蟲腈(dicyclanil)、二硫松(disulfoton)、達特南(dinotefuran)、敌蟎通(dinobuton)、氯氟氰蟲醯胺(cyhalodiamide)、賽洛寧(cyhalothrin)[包含γ-體，λ-體]、賽芬寧(cyphenothrin)[包含(1R)-反式-體]、賽扶寧(cyfluthrin)[包含β-體]、二福隆(diflubenzuron)、賽芬蟎(cyflumetofen)、氟蟎

Figure 108129126-A0202-12-0159-175
(diflovidazin)、錫滿丹(cyhexatin)、亞滅寧(cypermethrin)[包含α-體、β-體、θ-體、ζ-體]、dimpropyridaz(通用名)、二甲基-2,2,2-三氯-1-羥乙基膦酸酯(DEP)、甲基毒蟲畏(dimethylvinphos)、大滅松(dimethoate)、四氟甲醚菊酯(dimefluthrin)、矽護芬(silafluofen)、賽滅淨(cyromazine)、賜諾特(spinetoram)、賜諾殺(spinosad)、賜派芬(spirodiclofen)、賜滅派(spirotetramat)、spiropidion(通用名)、賜滅芬(spiromesifen)、速克吩鈉鹽(sulcofuron-sodium)、氟蟲胺(sulfluramid)、碸蟲啶(sulfoxaflor)、治螟磷(sulfotep)、大利松(diazinon)、賽果培(thiacloprid)、賽速安(thiamethoxam)、tioxazafen(通用名)、硫敵克(thiodicarb)、硫賜安(thiocyclam)、殺蟲雙(thiosultap)、硫磷
Figure 108129126-A0202-12-0159-176
(thionazin)、硫伐隆(thiofanox)、硫滅松(thiometon)、tyclopyrazoflor(通用名)、四剋安勃(tetrachlorantraniliprole)、樂本松(tetrachlorvinphos)、得脫蟎 (tetradifon)、氟氰蟲醯胺(tetraniliprole)、四氟醚菊酯(tetramethylfluthrin)、治滅寧(tetramethrin)、丁基嘧啶磷(tebupirimfos)、得芬諾(tebufenozide)、得芬瑞(tebufenpyrad)、汰福寧(tefluthrin)、得福隆(teflubenzuron)、滅賜松(demeton-S-methyl)、雙硫磷(temephos)、第滅寧(deltamethrin)、托福松(terbufos)、泰滅寧(tralomethrin)、拜富寧(transfluthrin)、唑蚜威(triazamate)、三落松(triazophos)、三氯松(trichlorfon)、殺蟲隆(triflumuron)、三氟苯嘧啶(triflumezopyrim)、混殺威(trimethacarb)、脫芬瑞(tolfenpyrad)、乃力松(naled)、尼古丁(nicotine)、烯啶蟲胺(nitenpyram)、尼莫克汀(nemadectin)、諾伐隆(novaluron)、諾福隆(noviflumuron)、臘蚧輪刺抱菌(Verticillium lecanii)、烯蟲乙酯(hydroprene)、液化澱粉芽孢桿菌(Bacillus amyloliquefaciens)、堅強芽孢桿菌(Bacillus firmus)、球形芽孢桿菌(Bacillus sphaericus)、枯草桿菌(Bacillus subtillis)、蘇力菌(Bacillus thuringiensis)、蘇力菌(Bacillus thuringiensis)生產的昆蟲毒素、蘇力菌相澤氏亞種(Bacillus thuringiensis subsp.Aizawai)、蘇力菌以色列亞種(Bacillus thuringiensis subsp.Israelensis)、蘇力菌庫斯克亞種(Bacillus thuringiensis subsp.Kurstaki)、蘇力菌擬步行亞種(Bacillus thuringiensis subsp.Tenebrionis)、日本甲蟲芽孢桿菌(Bacillus popilliae)、巴斯德穿刺桿菌胞子(Pasteuriapenetrans spore)、繁米松(vamidothion)、巴拉松(parathion)、甲基巴拉松(parathion-methyl)、合芬寧(halfenprox)、合芬隆(halofenozide)、二丙烯除蟲菊酯(bioallethrin)、S-環戊烯基二丙烯除蟲菊酯(bioallethrin S-cyclopentenyl)、苄呋菊酯(bioresmethrin)、雙-(2-氯-1-甲基乙基)醚(DCIP)、雙三氟蟲脲 (bistrifluron)、愛美松(hydramethylnon)必芬蟎(bifenazate)、畢芬寧(bifenthrin)、氟他胺(pyflubumide)、協力精(piperonyl butoxide)、派滅淨(pymetrozine)、白克松(pyraclofos)、派福若(pyrafluprole)、必芬松(pyridaphenthion)、畢達本(pyridaben)、三氟甲吡醚(pyridalyl)、哌氟喹腙(pyrifluquinazon)、吡普若(pyriprole)、百利普芬(pyriproxyfen)、比加普(pirimicarb)、畢汰芬(pyrimidifen)、嘧蟎胺(pyriminostrobin)、甲基亞特松(pirimiphos-methyl)、除蟲菊素(pyrethrine)、氨磺磷(famphur)、芬普尼(fipronil)、芬殺蟎(fenazaquin)、芬滅松(fenamiphos)、撲滅松(fenitrothion)、芬諾克(fenoxycarb)、芬硫克(fenothiocarb)、酚丁滅蝨(phenothrin)[包含(1R)-反式-體]、丁基滅必蝨(fenobucarb)、芬殺松(fenthion)、賽達松(phenthoate)、芬化利(fenvalerate)、芬普蟎(fenpyroximate)、芬佈賜(fenbutatin oxide)、芬普寧(fenpropathrin)、大福松(fonofos)、磺醯氟(sulfuryl fluoride)、佈嘉信(butocarboxim)、丁酮碸威(butoxycarboxim)、布芬淨(buprofezin)、呋線威(furathiocarb)、普亞列寧(prallethrin)、嘧蟎酯(fluacrypyrim)、三氟咪啶醯胺(fluazaindolizine)、克福隆(fluazuron)、氟速芬(fluensulfone)、福拜倫(fluopyram)、氟乙酸鈉鹽(sodium fluoroacetate)、fluxametamide(fluxametamide)、氟環脲(flucycloxuron)、護賽寧(flucythrinate)、氟硫滅(flusulfamide)、賽扶寧(fluthrin)、氟胺氰菊酯(fluvalinate)[包含τ-體]、氟吡呋喃酮(flupyradifurone)、吡氟硫磷(flupyrazofos)、flupyrimin(通用名)、丁蟲腈(flufiprole)、嘧蟲胺(flufenerim)、氟菌螨酯(flufenoxystrobin)、氟芬隆(flufenoxuron)、菲殺碸(fluhexafon)、氟大滅(flubendiamide)、氟氯苯菊酯 (flumethrin)、弗雷拉納(fluralaner)、氟蟲芬(flurimfen)、茉莉酮(jasmone)、順式-茉莉酮(cis-jasmone)、普硫松(prothiofos)、羅芬布(protrifenbute)、氟尼胺(flonicamid)、加護松(propaphos)、毆蟎多(propargite)、佈飛松(profenofos)、溴蟲氟苯雙醯胺(broflanilide)、四氟苯甲菊酯(profluthrin)、撲達松(propetamphos)、安丹(propoxur)、弗洛梅托昆(flometoquin)、新殺蟎(bromopropylate)、合賽多(hexythiazox)、六伏隆(hexaflumuron)、細腳擬青黴(Pacilimyces tenuipes)、玫煙色擬青黴(Paecilomyces fumosoroceus)、淡紫擬青黴菌(Paecilomyces lilacinus)、右旋七氟甲醚菊酯(heptafluthrin)、飛達松(heptenophos)、百滅寧(permethrin)、benclothiaz(benclothiaz)、benzpyrimoxan(通用名)、免速達(bensultap)、苯蟎特(benzoximate)、免敵克(bendiocarb)、免扶克(benfuracarb)、纖細白僵菌(Beauveria tenella)、巴氏蠶白僵菌(Beauveria bassiana)、布氏白僵菌(Beauveria brongniartii)、巴賽松(phoxim)、裕必松(phosalone)、福賽絕(fosthiazate)、丁硫環磷(fosthietan)、福賜米松(phosphamidon)、益滅松(phosmet)、抗蟎素複合體(polynactins)、覆滅璊(formetanate)、福瑞松(phorate)、機油(machine oil)、馬拉松(malathion)、密滅汀(milbemectin)、滅加松(mecarbam)、倍硫磷亞碸(mesulfenfos)、納乃得(methomyl)、聚乙醛(metaldehyde)、美氟綜(metaflumizone)、達馬松(methamidophos)、威百畝(metham)、滅賜克(methiocarb)、滅大松(methidathion)、異硫氰酸甲酯(methyl isothiocyanate)、溴化甲烷(methyl bromide)、甲氧氯(methoxychlor)、滅芬諾(methoxyfenozide)、對甲氧基甲基菊酯(methothrin)、美特寧(metofluthrin)、美賜平(methoprene)、治滅蝨 (metolcarb)、美文松(mevinphos)、氯氟醚菊酯(meperfluthrin)、瘤捕單頂孢菌(Monacrosporium phymatophagum)、亞素靈(monocrotophos)、沒氟菊酯(momfluorothrin)、哈氏木黴菌(Trichoderma harzianum)、夜蛾誘劑A(litlure-A)、夜蛾誘劑B(litlure-B)、磷化鋁(aluminium phosphide)、磷化鋅(zinc phosphide)、磷化氫(phosphine)、祿芬隆(lufenuron)、rescalure(紅圓蚧引誘劑)、列滅寧(resmethrin)、雷皮菌素(lepimectin)、魚藤精(rotenone)、核多角體病病毒包埋體、芬佈賜(fenbutatin oxide)、氰化鈣(calcium cyanide)、有機錫化合物(organotins)、硫酸尼古丁(nicotine-sulfate)、(Z)-11-十四烯基=乙酸酯、(Z)-11-十六碳烯醇、(Z)-11-十六碳烯基=乙酸酯、(Z)-9,12-十四碳二烯基=乙酸酯、(Z)-9-十四碳烯-1-醇、(Z,E)-9,11-十四碳二烯基=乙酸酯、(Z,E)-9,12-十四碳二烯基=乙酸酯、1,1,1-三氯-2,2-雙(4-氯苯基)乙烷(DDT)、1,3-二氯丙烯(1,3-dichloropropene)、2-氯-4-氟-5-[(5-三氟甲)基硫基)戊基氧]苯基2,2,2-三氟乙基亞碸(化學名，CAS登錄號碼：1472050-04-6)、2,4-二氯-5-{2-[4-(三氟甲基)苯基]乙氧基}苯基2,2,2-三氟乙基亞碸(化學名，CAS登錄號碼：1472052-11-1)、2,4-二甲基-5-[6-(三氟甲)基硫基)己氧基]苯基-2,2,2-三氟乙基亞碸(化學名，CAS登錄號碼：1472050-34-2)、2-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)亞磺醯基]苯氧基}-5-(三氟甲基)吡啶(化學名，CAS登錄號碼：1448758-62-0)、3-氯-2-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)亞磺醯基]苯氧基}-5-(三氟甲基)吡啶(化學名，CAS登錄號碼：1448761-28-1)、4,6-二硝基-o-甲酚(DNOC)、4-氟-2-甲基-5-(5,5-二甲基己氧基]苯基2,2,2-三氟乙基亞碸(化學名，CAS登錄號碼：1472047-71-4)、Bt蛋白質(Cry1Ab、 Cry1Ac、Cry1Fa、Cry2Ab、mCry3A、Cry3Ab、Cry3Bb、Cry34/35Ab1)、CL900167(編碼序號)、NA-85(編碼序號)、NI-30(編碼序號)、O,O-二乙基-O-[4-(二甲基胺磺醯基)苯基]-硫代磷酸酯(DSP)、O-乙基-O-4-(硝基苯基)苯基硫代臉酸酯(EPN)、RU15525(編碼序號)、XMC(XMC)、Z-13-二十碳烯-10-酮、ZXI8901(編碼序號)、F4260(編碼序號)。 Anacrinthrin, azadirachtin, azamethiphos, acynonapyr (common name), azinphos-ethyl, azinphos-methyl, azinphos-methyl, Acequinocyl, acetamiprid, acetoprole, acephate, azocyclotin, abamectin, afidopyropen , Afoxolaner, amidoflumet, amitraz, alanycarb, aldicarb, aldoxycarb, allethrin [ Contains d-cis-trans-body, d-trans-body], isazophos, isamidofos, isocarbophos, isoxathion, isocycloseram (general purpose Name), isofenphos-methyl, isoprocarb, epsilon-metofluthrin, epsilon-metofluthrin (epsilon- momfluorothrin), ivermectin, imicyafos, imidacloprid, imiprothrin, indoxacarb, esfenvalerate, ethiofencarb ), ethion, ethiprole, ethylene dibromide, etoxazole, etofenprox, ethoprophos, etrimfos ), emamectin, emamectin benzoate, endosulfan, empenthrin, oxazosulfyl (common name), oxamyl, oxydemeton-methyl ), oxydeprofos, omethoate, cadusafos, κ-tefluthrin, κ-bifenthri n), karanjin, cartap, carbaryl, butyl carbosulfan, carbosulfan, carbofuran, γ-BHC (gamma-BHC), chlor Lice (xylylcarb), quinalphos, kinoprene, chinomethionat, coumaphos, cryolite, clothianidin, kefir mite (clofentezine), chromafenozide, chlorantraniliprole, chlorethoxyfos, chlordane, chloropicrin, chlorpyrifos, chlorpyrifos-methyl ), chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chloroprallethrin, cyazypyr ), cyanophos, diafenthiuron, diamidafos, cyantraniliprole, dienochlor, cyenopyrafen, dioxabenzofos ), diofenolan, cyclaniliprole, cycloxaprid, dicrotophos, dichlofenthion, cycloprothrin, dichloro Pine (dichlorvos), dicloromezotiaz (common name), dicofol, dicyclanil, disulfoton, dinotefuran, dinobuton, chlorofluorocyanide Cyhalodiamide, cyhalothrin [containing γ-body, λ-body], cyphenothrin [containing (1R)-trans-body], cyfluthrin [containing β -Body], diflubenzuron, cyflumetofen, fluoromite
Figure 108129126-A0202-12-0159-175
(diflovidazin), cyhexatin, cypermethrin [including α-body, β-body, θ-body, ζ-body], dimpropyridaz (common name), dimethyl-2,2, 2-trichloro-1-hydroxyethylphosphonate (DEP), dimethylvinphos, dimethoate, dimefluthrin, silafluofen, Cyromazine, spinotoram, spinosad, spirodiclofen, spirotetramat, spiropidion (common name), spiromesifen, speed Sulcofuron-sodium, sulfluramid, sulfoxaflor, sulfotep, diazinon, thiacloprid, thiamethoxam, tioxazafen (common name), thiodicarb, thiocyclam, thiosultap, thiophosphor
Figure 108129126-A0202-12-0159-176
(thionazin), thiofanox, thiometon, tyclopyrazoflor (general name), tetrachlorantraniliprole, tetrachlorantraniliprole, tetrachlorvinphos, tetradifon, chlorfenapyr Amine (tetraniliprole), tetramethylfluthrin, tetramethrin, tetramethrin, tebupirimfos, tebufenozide, tebufenpyrad, tefluthrin, Teflubenzuron, demeton-S-methyl, temephos, deltamethrin, terbufos, tralomethrin, transfluthrin ), triazamate, triazophos, trichlorfon, triflumuron, triflumezopyrim, trimethacarb, tolfenpyrad ), naled, nicotine, nitenpyram, nemadectin, novaluron, noviflumuron, and Pseudoceras (Verticillium lecanii), hydroprene, Bacillus amyloliquefaciens, Bacillus firmus, Bacillus sphaericus, Bacillus subtillis, Bacillus thuringiensis), insect toxin produced by Bacillus thuringiensis, Bacillus thuringiensis subsp.Aizawai, Bacillus thuringiensis subsp.Israelensis, Sullicus cusca Species (Bacillus thuringiensis subsp. Kurstaki), Bacillus turingiensis subsp. (Bacillus t huringiensis subsp.Tenebrionis), Bacillus popilliae, Pasteuriapenetrans spore, vamidothion, parathion, parathion-methyl, Halfenprox, halofenozide, bioallethrin, bioallethrin S-cyclopentenyl, bioresmethrin , Bis-(2-chloro-1-methylethyl) ether (DCIP), bistrifluron (bistrifluron), hydramethylnon (bifenazate), bifenthrin (bifenthrin), flutamide ( pyflubumide, piperonyl butoxide, pymetrozine, pyraclofos, pyrafluprole, pyridaphenthion, pyridaben, pyridalyl ), pyrifluquinazon, pyriprole, pyriproxyfen, pirimicarb, pyrimidifen, pyriminostrobin, methylyate Pine (pirimiphos-methyl), pyrethrine (pyrethrine), sulfamethoxam (famphur), fenpronil (fipronil), fenazaquin (fenazaquin), fenamiphos (fenamiphos), fenmazon (fenitrothion), fen Fenoxycarb, Fenothiocarb, Phenothrin [including (1R)-trans-body], Fenobucarb, Fenthion, Saida Phenthoate, fenvalerate, fenpyroximate, fenbutatin oxide, fenpropathrin, fenpropathrin, fonofos, sulfonyl fluoride, bujiaxin ( butocarboxim), butoxycarbox im), buprofezin, furathiocarb, prallethrin, fluacrypyrim, fluazaindolizine, fluazuron, fluazuron Fluensulfone, Fluopyram, sodium fluoroacetate, fluxametamide (fluxametamide), flucycloxuron, flucythrinate, flusulfamide, flusulfamide, and safinin (fluthrin), fluvalinate [containing τ-body], flupyradifurone, flupyrazofos, flupyrimin (common name), flufiprole, pyrimidine Flufenerim, flufenoxystrobin, flufenoxuron, fluhexafon, flubendiamide, flumethrin, fluralaner , Flurimfen, jasmone, cis-jasmone, prothiofos, protrifenbute, flonicamid, propaphos ), propargite, profenofos, broflanilide, profluthrin, propetamphos, propoxur, propofol Flometoquin, bromopropylate, hexythiazox, hexaflumuron, Pacilimyces tenuipes, Paecilomyces fumosoroceus, lilac Paecilomyces lilacinus, heptafluthrin, heptenophos, permethrin, benclothiaz (benclothiaz), benzpyrimoxan (common name), bensulta p), benzoximate, bendiocarb, benfuracarb, Beauveria tenella, Beauveria bassiana, Beauveria bassiana ( Beauveria brongniartii), phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosmet, anti-mite Polynactins, formetanate, phorate, machine oil, malathion, milbemectin, mecarbam, mesulfenfos ), metomyl, metaldehyde, metaflumizone, methamidophos, metham, methiocarb, methidathion, Methyl isothiocyanate, methyl bromide, methoxychlor, methoxyfenozide, methothrin, metofluthrin ), metoprene, metolcarb, mevinphos, meperfluthrin, Monacrosporium phymatophagum, monocrotophos, no Momfluorothrin, Trichoderma harzianum, Spodoptera lure A (litlure-A), Spodoptera lure B (litlure-B), aluminum phosphide, zinc phosphide ( zinc phosphide, phosphine, lufenuron, rescalure (red attractant), resmethrin, lepimectin, rotenone, nucleus Polyhedrosis virus embedded body, fenbutatin oxide, calcium cyani de), organic tin compounds (organotins), nicotine sulfate (nicotine-sulfate), (Z)-11-tetradecenyl = acetate, (Z)-11-hexadecenol, (Z)-11 -Hexadecenyl=acetate, (Z)-9,12-tetradecadienyl=acetate, (Z)-9-tetradecen-1-ol, (Z,E) -9,11-tetradecadienyl=acetate, (Z,E)-9,12-tetradecadienyl=acetate, 1,1,1-trichloro-2,2- Bis(4-chlorophenyl)ethane (DDT), 1,3-dichloropropene (1,3-dichloropropene), 2-chloro-4-fluoro-5-[(5-trifluoromethyl)thio )Pentyloxy]phenyl 2,2,2-trifluoroethyl sulfoxide (chemical name, CAS registration number: 1472050-04-6), 2,4-dichloro-5-{2-[4-( Trifluoromethyl)phenyl]ethoxy}phenyl 2,2,2-trifluoroethyl sulfoxide (chemical name, CAS registration number: 1472052-11-1), 2,4-dimethyl-5 -[6-(trifluoromethyl)thio)hexyloxy]phenyl-2,2,2-trifluoroethyl sulfoxide (chemical name, CAS registration number: 1472050-34-2), 2-{ 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenoxy}-5-(trifluoromethyl)pyridine (chemical name, CAS registration number : 1448758-62-0), 3-chloro-2-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenoxy}-5 -(Trifluoromethyl)pyridine (chemical name, CAS registration number: 1448761-28-1), 4,6-dinitro-o-cresol (DNOC), 4-fluoro-2-methyl-5- (5,5-dimethylhexyloxy)phenyl 2,2,2-trifluoroethyl sulfoxide (chemical name, CAS registration number: 1472047-71-4), Bt protein (Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1), CL900167 (coding serial number), NA-85 (coding serial number), NI-30 (coding serial number), O,O-diethyl-O-(4-(two (Methylsulfamoyl) phenyl]-thiophosphate (DSP), O-ethyl-O-4-(nitrophenyl) phenyl thiofacet (EPN), RU15525 (coding number) , XMC (XMC), Z-13-Eicosene-10-one, ZXI8901 (coding serial number), F4260 (coding serial number).

其次，例示可以混合或併用的公知的殺菌劑或病害防除劑化合物。 Next, exemplified well-known fungicides or disease control compound compounds that can be mixed or used together.

殺菌活性成分： Bactericidal active ingredients:

阿扎康唑(azaconazole)、噻二唑素-S-甲基(acibenzolar-S-methyl)、亞托敏(azoxystrobin)、敵菌靈(anilazine)、安美速(amisulbrom)、aminopyrifen(通用名)、滅脫定(ametoctradin)、艾迪嗎林(aldimorph)、亞汰尼(isotianil)、益拜若(isopyrazam)、艾索非他滅(isofetamid)、異丙噻菌胺(isoflucypram)、亞賜圃(isoprothiolane)、種菌唑(ipconazole)、ipflufenoquin(通用名)、ipfentrifluconazole(通用名)、依普同(iprodione)、丙森辛(iprovalicarb)、丙基喜樂松(iprobenfos)、依滅列(imazalil)、雙胍辛胺烷苯磺酸鹽(iminoctadine-albesilate)、雙胍辛胺乙酸鹽(iminoctadine-triacetate)、易胺座(imibenconazole)、inpyrfluxam(通用名)、imprimatin A(植物免疫引發化合物)、imprimatin B(植物免疫引發化合物)、護粒松(edifenphos)、乙環唑(etaconazole)、噻唑菌胺(ethaboxam)、依瑞莫(ethirimol)、乙氧基喹因(ethoxyquin)、依得利(etridiazole)、烯肟菌酯(enestroburin)、烯肟菌酯(enoxastrobin)、依普座(epoxiconazole)、有機油(organic oils)、歐殺斯(oxadixyl)、噁嗪拉唑(oxazinylazole)、奧賽普林 (oxathiapiprolin)、嘉保信(oxycarboxin)、快得寧(oxine-copper)、土黴素(oxytetracycline)、

Figure 108129126-A0202-12-0165-177
咪唑反丁烯二酸鹽(oxpoconazole-fumarate)、歐索林酸(oxolinic acid)、二辛酸銅(copper dioctanoate)、辛異噻啉酮(octhilinone)、呋醯胺(ofurace)、肟醚菌胺(orysastrobin)、鄰苯基苯酚(o-phenylphenol)、嘉賜黴素(kasugamycin)、四氯丹(captafol)、加普胺(carpropamid)、加保扶(carbendazim)、嘉保信(carboxin)、香旱芹酮(carvone)、快諾芬(quinoxyfen)、quinofumelin(通用名)、蟎離丹(chinomethionat)、蓋普丹(captan)、喹康唑(quinconazole)、五氯硝苯(quintozene)、雙胍鹽(guazatine)、銅合浦單劑(cufraneb)、甲香菌酯(coumethoxystrobin)、丁香菌酯.(coumoxystrobin)、克收欣(kresoxim-methyl)、抑霉胺(clozylacon)、克氯得(chlozolinate)、四氯異苯腈(chlorothalonil)、地茂散(chloroneb)、賽座滅(cyazofamid)、乙霉威(diethofencarb)、雙氯氰菌胺(diclocymet)、益發靈(dichlofluanid)、dichlobentiazox(通用名)、達滅淨(diclomezine)、大克爛(dicloran)、雙氯酚(dichlorophen)、二氰蒽醌(dithianon)、達克利(diniconazole)、達克利-M(diniconazole-M)、鋅乃浦(zineb)、白粉克(dinocap)、dipymetitrone(通用名)、二苯基胺(diphenylamine)、二待克利(difenoconazole)、賽芬胺(cyflufenamid)、二氟林(diflumetorim)、環克座(cyproconazole)、賽普洛(cyprodinil)、硅氟唑(simeconazole)、二甲嘧酚(dimethirimol)、二硫二甲烷(dimethyl disulfide)、達滅芬(dimethomorph)、克絕(cymoxanil)、醚菌胺(dimoxystrobin)、霍氏假單胞菌HAI-0804(Pseudomonas rhodesiae HAI-0804)、吉闌(ziram)、硅噻菌胺(silthiofam)、鏈黴素(streptomycin)、 螺環菌胺(spiroxamine)、先正達(sedaxane)、座賽胺(zoxamide)、苯並烯氟菌唑(solatenol)、邁隆(dazomet)、黃藍狀菌(Talaromyces flavus)、噻醯菌胺(tiadinil)、腐絕(thiabendazole)、福美雙(thiram)、多保淨(thiophanate)、甲基多保淨(thiophanate-methyl)、賽氟滅(thifluzamide)、福美雙(thiram)、四氯硝基苯(tecnazene)、克枯爛(tecloftalam)、四克利(tetraconazole)、咪菌威(debacarb)、得克利(tebuconazole)、氟硅唑(tebufloquin)、療黴舒(terbinafine)、多寧(dodine)、嗎菌靈(dodemorph)、三泰隆(triadimenol)、三泰芬(triadimefon)、咪唑
Figure 108129126-A0202-12-0166-178
(triazoxide)、水楊菌胺(trichlamide)、氯啶菌酯(triclopyricarb)、深綠木霉(Trichoderma atroviride)、三賽唑(tricyclazole)、滅菌唑(triticonazole)、三得芬(tridemorph)、賽福座(triflumizole)三氟敏(trifloxystrobin)、賽福寧(triforine)、甲基益發靈(tolylfluanid)、脫克松(tolclofos-methyl)、甲磺菌胺(tolnifanide)、托普洛卡(tolprocarb)、代森鈉(nabam)、納他黴素(natamycin)、萘替芬(naftifine)、氯草定(nitrapyrin)、酞菌酯(nitrothal-isopropyl)、尼瑞莫(nuarimol)、壬基酚磺酸銅(copper nonyl phenol sulphonate)、枯草桿菌(Bacillus subtilis)(菌株：QST 713)、維利黴素(validamycin)、伐利芬(valifenalate)、皮卡布西(picarbutrazox)、聯苯吡菌胺(bixafen)、啶氧菌酯(picoxystrobin)、pydiflumetofen(通用名)、比多農(bitertanol)、樂殺蟎(binapacryl)、β-檜酚酮(hinokitiol)、聯苯(biphenyl)、哌丙靈(piperalin)、殺紋寧(hymexazol)、唑菌酯(pyraoxystrobin)、百克敏(pyraclostrobin)、pyraziflumid(通用名)、白粉松(pyrazophos)、pyrapropoyne(通用名)、唑胺菌酯(pyrametostrobin)、pyriofenone(通用名)、啶菌
Figure 108129126-A0202-12-0166-179
唑(pyrisoxazole)、氟醚菌醯胺 (pyridachlometyl)、比芬諾(pyrifenox)、稗草畏(pyributicarb)、吡菌苯威(pyribencarb)、派美尼(pyrimethanil)、百快隆(pyroquilon)、免克寧(vinclozolin)、福美鐵(ferbam)、凡殺同(famoxadone)、吩
Figure 108129126-A0202-12-0167-180
氧化物(phenazine oxide)、咪唑菌酮(fenamidone)、烯肟菌胺(fenaminstrobin)、芬瑞莫(fenarimol)、芬諾尼(fenoxanil)、富米綜(ferimzone)、拌種咯(fenpiclonil)、fenpicoxamid(通用名)、胺苯吡菌酮(fenpyrazamine)、芬克座(fenbuconazole)、甲呋醯胺(fenfuram)、苯锈啶(fenpropidin)、芬普福(fenpropimorph)、環菌胺(fenhexamid)、福爾培(folpet)、熱必斯(phthalide)、布瑞莫(bupirimate)、麥穗靈(fuberidazole)、滅瘟素-S(blasticidin-S)、福拉比(furametpyr)、呋霜靈(furalaxyl)、呋喃羧酸(furancarboxylic acid)、呋霜靈(fluazinam)、氟茚唑菌胺(fluindapyr)、氟嘧菌酯(fluoxastrobin)、fluoxapiprolin(通用名)、氟比來(fluopicolide)、氟醚菌醯胺(fluopimomide)、福拜倫(fluopyram)、氟氯菌核利(fluoroimide)、福賽斯(fluxapyroxad)、氟喹唑(fluquinconazole)、氟康唑(furconazole)、順式氟康唑(furconazole-cis)、護汰寧(fludioxonil)、護矽得(flusilazole)、氟硫滅(flusulfamide)、氟噻唑(flutianil)、福多寧(flutolanil)、護汰芬(flutriafol)、氟菌蟎酯(flufenoxystrobin)、氟醯菌胺(flumetover)、氟嗎啉(flumorph)、普快淨(proquinazid)、撲克拉(prochloraz)、撲滅寧(procymidone)、硫菌威(prothiocarb)、丙硫菌唑(prothioconazole)、溴硝丙二醇(bronopol)、普拔克鹽酸鹽(propamocarb-hydrochloride)、普克利(propiconazole)、丙森锌(propineb)、撲殺熱(probenazole)、溴克座(bromuconazole)、氟美多喹(flometoquin)、florylpicoxamid(通用名)、菲 克利(hexaconazole)、本達樂(benalaxyl)、本達樂M(benalaxyl-M)、麥銹靈(benodanil)、苯菌靈(benomyl)、披扶座(pefurazoate)、平克座(penconazole)、賓克隆(pencycuron)、苯并烯氟菌唑(benzovindiflupyr)、佈生(benthiazole)、苯噻菌胺(benthiavalicarb-isopropyl)、吡噻菌胺(penthiopyrad)、平氟芬(penflufen)、白克列(boscalid)、福賽得(fosetyl)(alminium，calcium，sodium)、多抗霉素(polyoxin)、福代鋅(polycarbamate)、波爾多液(Bordeaux mixture)、代森錳銅(mancopper)、鋅錳乃浦(mancozeb)、曼普胺(mandipropamid)、滿得賓(mandestrobin)、錳乃浦(maneb)、邁克尼(myclobutanil)、礦油(mineral oils)、米多霉素(mildiomycin)、滅速克(methasulfocarb)、威百畝(metam)、右滅達樂(metalaxyl)、右滅達樂M(metalaxyl-M)、代森聯(metiram)、metyltetraprole(通用名，苯基吡唑類)、滅特座(metconazole)、苯氧菌胺(metominostrobin)、滅芬農(metrafenone)、滅派林(mepanipyrim)、氯氟醚菌唑(mefentrifluconazole)、敵蟎普(meptyldinocap)、滅普寧(mepronil)、碘克(iodocarb)、海帶多醣(laminarin)、葡萄根瘤菌(Rhizobium vitis)、亞磷酸及鹽(phosphorous acid and salts)、鹼性氯化銅(copper oxychloride)、銀(silver)、氧化亞銅(cuprous oxide)、氫氧化銅(copper hydroxide)、碳酸氫鉀(potassium bicarbonate)、碳酸氫鈉(sodium bicarbonate)、硫(sulfur)、硫酸羥基喹啉(oxyquinoline sulfate)、硫酸銅(copper sulfate)、(3,4-二氯異噻唑-5-基)甲基4-(第三丁基)苯甲酸酯(化學名，CAS登錄號碼：1231214-23-5)、BAF-045(編碼序號)、BAG-010(編碼序號)、UK-2A(編碼序號)、十二烷基苯磺酸雙乙烯二胺銅錯鹽[II](DBEDC)、MIF-1002(編碼序號)、 NF-180(編碼序號)、乙酸三苯基錫(TPTA)、三苯基氯化錫(TPTC)、氫氧化三苯基錫(TPTH)、非病原性Erwinia carotovora，F9650(編碼序號)。 Azaconazole, acibenzolar-S-methyl, azoxystrobin, anilazine, anisulbrom, aminopyrifen (common name) , Ametoctradin, aldimorph, isotianil, isopyrazam, isofetamid, isoflucypram, and aci Isoprothiolane, ipconazole, ipflufenoquin (common name), ipfentrifluconazole (common name), iprodione, iprodione, iprovalicarb, iprobenfos, imazalil ), iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, inpyrfluxam (common name), imprimatin A (plant immune inducing compound), imprimatin B (plant immune triggering compound), edifenphos, etaconazole, ethaboxam, ethirimol, ethoxyquin, and etridiazole ), enestroburin, enoxastrobin, epoxiconazole, organic oils, oxadixyl, oxazinylazole, oxseprine (oxathiapiprolin), oxycarboxin, oxine-copper, oxytetracycline,
Figure 108129126-A0202-12-0165-177
Oxpoconazole-fumarate, oxolinic acid, copper dioctanoate, octhilinone, octhilinone, ofurace, and oxamid (orysastrobin), o-phenylphenol, kasugamycin, captafol, carpropamid, carbendazim, carboxin, incense Carvone, quinoxyfen, quinofumelin (common name), chinomethionat, captan, quinconazole, quintozene, biguanide (guazatine), cufraneb, coumethoxystrobin, syringamate (coumoxystrobin), kresoxim-methyl, clozylacon, chlozolinate , Chlorothalonil, chloroneb, cyazofamid, diethofencarb, diclocymet, dichlofluanid, dichlobentiazox (common name) ), diclomezine, dicloran, dichlorophen, dithianon, diniconazole, diniconazole-M, zinc naipura (zineb), dinocap, dipymetitrone (common name), diphenylamine (diphenylamine), diifenoconazole, cyflufenamid, diflumetorim, cyproconazole ), cyprodinil, simeconazole, dimethirimol, dimethyl disulfide, dimethomorph, cymoxanil, and tebufenol ( dimoxystrobin), Pseudomonas cholerae HAI-0804 (Pseu domonas rhodesiae HAI-0804), ziram, silthiofam, streptomycin, spiroxamine, sedaxane, zoxamide, Solatenol, dazomet, Talaromyces flavus, tiadinil, thiabendazole, thiram, thiophanate ), thiophanate-methyl, thifluzamide, thiram, tecnazene, tecloftalam, tetraconazole, imibacillus Debacarb, tebuconazole, tebufloquin, terbinafine, dodine, dodemorph, triadimenol, triadimefon Imidazole
Figure 108129126-A0202-12-0166-178
(triazoxide), trichlamide, triclopyricarb, Trichoderma atroviride, tricyclazole, trigononazole, tridmorph Triflumizole trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl, tolnifanide, tolprocarb ), nabam, natamycin, naftifine, nitrapyrin, nitrothal-isopropyl, nuarimol, nonylphenol Copper nonyl phenol sulphonate, Bacillus subtilis (strain: QST 713), valithromycin (validamycin), valifenalate, picarbutrazox, bifenpyr (bixafen), picoxystrobin, pydiflumetofen (common name), bitertanol (bitertanol), binapacryl, β-hinokitiol, biphenyl, piperazine (piperalin), hymexazol, pyraoxystrobin, pyraclostrobin, pyraziflumid (common name), pyrazophos, pyrapropoyne (common name), pyramethostrobin (pyrametostrobin), pyriofenone (common name), pyridoxine
Figure 108129126-A0202-12-0166-179
Pyrisoxazole, pyridachlometyl, pyrifenox, pyributicarb, pyrribencarb, pyrimethanil, pyroquilon, Vinclozolin, ferbam, famoxadone, phen
Figure 108129126-A0202-12-0167-180
Oxide (phenazine oxide), fenamidone, fenaminstrobin, fenarimol, fenoxanil, ferimzone, fenpiclonil, fenpicoxamid (common name), fenpyrazamine, fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid , Folpet, phthalide, bupirimate, fuberidazole, blasticidin-S, furametpyr, furaxyl (furalaxyl), furancarboxylic acid, fluazinam, fluindapyr, fluoxastrobin, fluoxapiprolin (common name), fluopicolide, fluorine Fluopimomide, fluopyram, fluoroimide, fluxapyroxad, fluquinconazole, fluconconazole, cisfluconazole (furconazole-cis), fludioxonil, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fludioxol Flufenoxystrobin, flumetover, flumorph, proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole (prothioconazole), bronopol, propamocarb-hydrochloride, propiconazole, propineb, probenazole, bromuconazole, fluorine Flometoquin, florylpicox amid (common name), hexaconazole, benalaxyl, benalaxyl-M, benodanil, benomyl, pefurazoate, Penconazole, pencycuron, benzovindiflupyr, benthiazole, benthiavalicarb-isopropyl, penthiopyrad, penflufen (penflufen), boscalid, fosetyl (alminium, calcium, sodium), polyoxin, polycarbamate, Bordeaux mixture, mancozeb Copper, mancozeb, mancozeb, mandipropamid, mandestrobin, maneb, myclobutanil, mineral oils, and mildew Mildiomycin, methasulfocarb, metam, metalaxyl, metalaxyl-M, metiram, metyltetraprole (common name, (Phenylpyrazoles), metconazole, metominostrobin, metrafenone, mepanipyrim, mefentrifluconazole, mepteridinocap ), mepronil, iodocarb, laminin, Rhizobium vitis, phosphorous acid and salts, copper oxychloride, silver (silver), cuprous oxide, copper hydroxide, potassium bicarbonate, sodium bicarbonate, sulfur, oxyquinoline sulfate, Copper sulfat e), (3,4-dichloroisothiazol-5-yl)methyl 4-(third butyl) benzoate (chemical name, CAS registration number: 1231214-23-5), BAF-045( (Code No.), BAG-010 (Code No.), UK-2A (Code No.), dodecylbenzenesulfonic acid diethylenediamine copper salt [II] (DBEDC), MIF-1002 (Code No.), NF -180 (coding number), triphenyltin acetate (TPTA), triphenyltin chloride (TPTC), triphenyltin hydroxide (TPTH), non-pathogenic Erwinia carotovora, F9650 (coding number).

其次，將可以混合或併用的公知的除草劑化合物、植物生長調整劑化合物例示如下述。 Next, the known herbicide compounds and plant growth regulator compounds that can be mixed or used together are exemplified as follows.

除草活性成分： Herbicidal active ingredients:

碘草腈(ioxynil)、苯草醚(aclonifen)、丙烯醛(acrolein)、草芬定(azafenidin)、亞喜芬(acifluorfen)(包含鈉等鹽)、四唑嘧磺隆(azimsulfuron)、亞速爛(asulam)、乙草胺(acetochlor)、草脫淨(atrazine)、莎稗磷(anilofos)、胺唑草酮(amicarbazone)、醯嘧磺隆(amidosulfuron)、滅草強(amitrole)、氯丙嘧啶酸(aminocyclopyrachlor)、氯胺吡啶酸(aminopyralid)、甲基胺草磷(amiprofos-methyl)、愛落殺(ametryn)、拉草(alachlor)、亞汰草(alloxydim)、環丙嘧啶醇(ancymidol)、愛速隆(isouron)、異

Figure 108129126-A0202-12-0169-181
氯草酮(isoxachlortole)、異
Figure 108129126-A0202-12-0169-182
唑草酮(isoxaflutole)、伊索本(isoxaben)、異癸醇乙氧基化物(Isodecylalkoholethoxylate)、異丙隆(isoproturon)、***醯草胺(ipfencarbazone)、滅草喹(imazaquin)、甲基咪草煙(imazapic)(包含胺等鹽)、依滅草(imazapyr)(包含異丙胺等鹽)、甲基咪草酸(imazamethabenz-methyl)、甲氧咪草煙(imazamox)、咪草烟(imazethapyr)、依速隆(imazosulfuron)、茚
Figure 108129126-A0202-12-0169-183
氟草胺(indaziflam)、茚草酮(indanofan)、甘草津(eglinazine-ethyl)、禾草畏(esprocarb)、甲磺隆(ethametsulfuro正methyl)、乙丁烯氟靈(ethalfluralin)、磺噻隆(ethidimuron)、亞速隆(ethoxysulfuron)、氯氟草醚乙酯(ethoxyfen-ethyl)、益覆滅(ethofumesate)、乙氧苯草胺(etobenzanid)、草藻滅(endothal-disodium)、樂滅草 (oxadiazon)、丙炔
Figure 108129126-A0202-12-0170-184
草酮(oxadiargyl)、
Figure 108129126-A0202-12-0170-185
草酮(oxaziclomefone)、環氧嘧磺隆(oxasulfuron)、復祿芬(oxyfluorfen)、歐拉靈(oryzalin)、嘧苯胺磺隆(orthosulfamuron)、坪草丹(orbencarb)、油酸(oleic acid)、苯酮唑(cafenstrole)、乙基克繁草(carfentrazone-ethyl)、特胺靈(karbutilate)、卡草胺(carbetamide)、快伏草(quizalofop)、快伏草(quizalofop-ethyl)、快伏草(quizalofop-P-ethyl)、喹禾糠酯(quizalofop-P-tefuryl)、莫克草(quinoclamine)、二氯喹啉酸(quinclorac)、氯甲喹啉酸(quinmerac)、苄草隆(cumyluron)、氯醯草膦(clacyfos)、嘉磷塞(glyphosate)(包含鈉、鉀、胺、丙基胺、異丙胺、二甲基胺或三甲基硫等鹽)、固殺草(glufosinate)(胺或鈉等鹽包含)、固殺草P(glufosinate-P)、固殺草P鈉鹽(glufosinate-P-sodium)、剋草同(clethodim)、clodinafop-炔丙基(clodinafop-propargyl)、畢克草(clopyralid)、可滅蹤(clomazone)、甲氧基護谷(chlomethoxyfen)、克普草(clomeprop)、氯酯磺草胺(cloransulam-methyl)、草滅平(chloramben)、殺草敏(chloridazon)、氯嘧磺隆(chlorimuron-ethyl)、氯磺隆(chlorsulfuron)、氯酸二甲酯(chlorthal-dimethyl)、草克樂(chlorthiamid)、氯醯亞胺(chlorphthalim)、整形素(chlorflurenol-methyl)、克普芬(chlorpropham)、氯溴隆(chlorbromuron)、枯草隆(chloroxuron)、綠麥隆(chlorotoluron)、ketospiradox(ketospiradox)(包含鈉、鈣或銨等鹽)、苯嘧磺草胺(saflufenacil)、假蒟亭鹼(sarmentine)、氰乃淨(cyanazine)、氰胺(cyanamide)、達有龍(diuron)、乙醯甲草胺(diethatyl-ethyl)、麥草畏(dicamba)(包含胺、二乙胺、異丙胺、二甘醇胺、鈉或鋰等鹽)、草滅特(cycloate)、環殺草(cycloxydim)、雙氯磺草安(diclosulam)、環磺隆 (cyclosulfamuron)、cyclopyranil(通用名，吡唑類除草劑)、cyclopyrimorate(通用名)、敵草腈(dichlobenil)、禾草靈(diclofop-P-methyl)、禾草靈(diclofop-methyl)、2,4滴丙酸鹽(dichlorprop)、2,4滴丙酸鹽-P(dichlorprop-P)、敵草快(diquat)、汰硫草(dithiopyr)、環草隆(siduron)、達乃安(dinitramine)、吲哚酮草酯(cinidon-ethyl)、醚磺隆(西速隆)(cinosulfuron)、達諾殺(dinoseb)、特垃酚(dinoterb)、氰氟草酯(cyhalofop-butyl)、大芬滅(diphenamid)、野燕枯(difenzoquat)、吡氟草胺(diflufenican)、二氟吡隆(diflufenzopyr)、草滅淨(simazine)、莫多草(dimethachlor)、愛落殺(dimethametryn)、汰草滅(dimethenamid)、汰草滅P(dimethenamid-P)、西草淨(simetryn)、哌草丹(dimepiperate)、
Figure 108129126-A0202-12-0171-186
唑隆(dimefuron)、環庚草醚(cinmethylin)、滅草靈(swep)、磺草酮(sulcotrione)、甲磺草胺(sulfentrazone)、草硫膦(sulfosate)、磺醯磺隆(sulfosulfuron)、甲嘧磺隆(sulfometuron-methyl)、西殺草(sethoxydim)、特草定(terbacil)、汰草龍(daimuron)、thaxtomin A(通用名)、茅草枯(dalapon)、噻草定(thiazopyr)、氟丙嘧草酯(tiafenacil)、噻酮磺隆(thiencarbazone)(包含鈉鹽、甲基酯等)、仲草(tiocarbazil)、禾草丹(thiobencarb)、噻苯隆(thidiazimin)、噻苯隆(thidiazuron)、甲基噻吩磺隆(thifensulfuron-methyl)、甜菜胺(desmedipham)、敵草淨(desmetryne)、tetflupyrolimet(通用名)、欣克草(thenylchlor)、牧草胺(tebutam)、特丁噻草隆(tebuthiuron)、得殺草(tepraloxydim)、特糠酯酮(tefuryltrione)、特丁津(terbuthylazine)、去草淨(terbutryn)、特丁通(terbumeton)、環磺酮(tembotrione)、苯唑草酮(topramezone)、肟草酮(tralkoxydim)、三
Figure 108129126-A0202-12-0171-187
氟草胺(triaziflam)、醚苯磺隆 (triasulfuron)、氟酮磺草胺(triafamone)、野麥畏(tri-allate)、草達津(trietazine)、綠草定(triclopyr)、三氯比(triclopyr-butotyl)、三氟甲磺隆(tritosulfuron)、trifludimoxazin(通用名)、氟胺磺隆(triflusulfuron-methyl)、氟樂靈(trifluralin)、三氟啶磺隆鈉鹽(trifloxysulfuron-sodium)、苯磺隆(tribenuron-methyl)、tolpyralate(通用名)、鈉得爛(naptalam)(包含鈉等鹽)、萘丙胺(naproanilide)、敵草胺(napropamide)、滅落脫(napropamide-M)、烟嘧磺隆(nicosulfuron)、草不隆(neburon)、氟草敏(norflurazon)、滅草猛(vernolate)、巴拉刈二氯鹽(paraquat dichloride)、氟氯吡啶酯(halauxifen-benzyl)、氟氯吡啶酯(halauxifen-methyl)、甲基合氯氟(haloxyfop)、甲基合氯氟(haloxyfop-P)、吡氟甲禾靈(haloxyfop-etotyl)、氟硝磺醯胺(halosafen)、氯吡嘧磺隆(halosulfuron-methyl)、bixlozone(bixlozone)、畢克爛(picloram)、氟吡醯草胺(picolinafen)、氟吡草酮(bicyclopyrone)、雙草醚(bispyribac-sodium)、唑啉草酯(pinoxaden)、必芬諾(bifenox)、哌草磷(piperophos)、雙唑草腈(pyraclonil)、磺醯草吡唑(pyrasulfotole)、苄草唑(pyrazoxyfen)、百速隆(pyrazosulfuron-ethyl)、苄草唑(pyrazolynate)、雙丙胺磷(bilanafos)、派芬草(pyraflufen-ethyl)、氯苯噠醇(pyridafol)、嘧硫草醚(pyrithiobac-sodium)、必汰草(pyridate)、環酯草醚(pyriftalid)、稗草畏(pyributicarb)、嘧啶肟草醚(pyribenzoxim)、pyrimisulfan(通用名)、甲基嘧草醚(pyriminobac-methyl)、碸吡草唑(pyroxasulfone)、甲氧磺草胺(pyroxsulam)、棉胺寧(phenisopham)、非草隆(fenuron)、fenoxasulfone(通用名)、
Figure 108129126-A0202-12-0172-188
唑禾草靈(fenoxaprop)(包含甲基、乙基、異丙基酯)、精
Figure 108129126-A0202-12-0172-189
唑禾草靈(fenoxaprop-P)(包含甲基、乙基、異丙基 酯)、fenquinotrione(通用名)、噻唑禾草靈(fenthiaprop-ethyl)、四唑醯草胺(fentrazamide)、甜菜寧(phenmedipham)、丁基拉草(butachlor)、布芬草(butafenacil)、丁胺磷(butamifos)、丁酸酯(butylate)、丁烯草胺(butenachlor)、比達寧(butralin)、丁苯草酮(butroxydim)、伏速隆(flazasulfuron)、麥草氟(flamprop)(包含甲基、乙基、異丙基酯)、麥草氟M(flamprop-M)(包含甲基、乙基、異丙基酯)、甲基氟嘧磺隆(primisulfuro 正methyl)、伏寄普(fluazifop-butyl)、伏寄普(fluazifop-P-butyl)、異丙吡草酯(fluazolate)、伏草隆(fluometuron)、乙羧氟草醚(fluoroglycofe正ethyl)、氟酮磺隆鈉鹽(flucarbazone-sodium)、氟消草(fluchloralin)、氟吡磺隆(flucetosulfuron)、
Figure 108129126-A0202-12-0173-190
草酸甲酯(fluthiacet-methyl)、氟啶嘧磺隆(flupyrsulfuro正methyl)(包含鈉、鈣或銨等鹽)、氟噻草胺(flufenacet)、氟嗒
Figure 108129126-A0202-12-0173-191
草酯(flufenpyr-ethyl)、氟丙酸酯(flupropanate)、氟洛普塞(flupoxame)、丙炔氟草胺(flumioxazin)、氟烯草酸(flumiclorac-pentyl)、唑嘧磺草胺(flumetsulam)、氟啶草酮(fluridone)、呋草酮(flurtamone)、氟氯比(fluroxypyr)(包含丁基甲酯、甲基庚酯等酯體，鈉、鈣或銨等鹽)、氟咯草酮(flurochloridone)、普拉草(pretilachlor)、甲基苄肼鈉鹽(procarbazone-sodium)、胺氟樂靈(prodiamine)、氟磺隆(prosulfuron)、苄草丹(prosulfocarb)、普拔草(propaquizafop)、毒草安(propachlor)、普拔根(propazine)、除草靈(propanil)、拿草特(propyzamide)、異丙草胺(propisochlor)、丙
Figure 108129126-A0202-12-0173-192
嘧磺隆(propyrisulfuron)、苯胺靈(propham)、氟唑草胺(profluazol)、調環酸鈣(prohexadione-calcium)、丙苯磺隆(propoxycarbazone)、丙苯磺隆(propoxycarbazone-sodium)、環苯草酮 (profoxydim)、除草定(bromacil)、溴殺草敏(brompyrazon)、撲草淨(prometryn)、撲滅通(prometon)、溴苯腈(bromoxynil)(包含丁酸、辛酸或庚酸等酯體)、殺草全(bromofenoxim)、溴芬諾(bromobutide)、雙氟磺草胺(florasulam)、氯氟吡啶酯(florpyrauxifen)、氯氟吡啶酯(florpyrauxifen-benzyl)、菲殺淨(hexazinone)烯草胺(pethoxamid)、草除靈(benazolin)、平速爛(penoxsulam)、heptamaloxyloglucan(heptamaloxyloglucan)、氟丁醯草胺(beflubutamid)、氟丁醯草胺-M(beflubutamid-M)、丁烯酸苯酯(pebulate)、壬酸(pelargonic acid)、茚蟲威(bencarbazone)、施得圃(pendimethalin)、雙苯嘧草酮(benzfendizone)、地散磷(bensulide)、免速隆(bensulfuron-methyl)、苯并雙環酮(benzobicyclon)、吡草酮(benzofenap)、滅草松(bentazone)、蔬草滅(pentanochlor)、環戊惡草酮(pentoxazone)、倍尼芬(benfluralin)、呋草黃(benfuresate)、殺木膦(fosamine)、氟磺胺草醚(fomesafen)、甲醯胺磺隆(foramsulfuron)、氯吡苯脲(forchlorfenuron)、2-甲基-4氯丙酸(mecoprop)(包含鈉、鉀、異丙胺、三乙醇胺、二甲基胺等鹽)、高甲氯丙酸鉀鹽(mecoprop-P-potassium)、甲磺胺磺窿(mesosulfuron)(包含甲酯等酯體)、硝磺草酮(mesotrione)、滅草胺(metazachlor)、
Figure 108129126-A0202-12-0174-193
吡嘧磺隆(metazosulfuron)、噻唑隆(methabenzthiazuron)、苯
Figure 108129126-A0202-12-0174-194
草酮(metamitron)、
Figure 108129126-A0202-12-0174-195
唑醯草胺(metamifop)、威百畝(metam)、甲基砷酸二鈉(DSMA)、methiozolin(通用名)、滅草隆(methyldymuron)、甲氧隆(metoxuron)、磺草唑胺(metosulam)、甲磺隆(metsulfuron-methyl)、撲奪草(metobromuron)、甲氧苯草隆(metobenzuron)、莫多草(metolachlor)、滅必淨(metribuzin)、縮節胺(mepiquat chloride)、滅芬草(mefenacet)、單嘧 磺隆(monosulfuron)(包含甲基、乙基、異丙基酯)、氯谷隆(monolinuron)、禾草敵(molinate)、碘磺隆(iodosulfuron)、甲基二磺隆鈉鹽(iodosulfulon-methyl-sodium)、iofensulfuron(iofensulfuron)、鵬橫隆-乙基鈉(iofensulfuron-sodium)、乳氟禾草靈(lactofen)、lancotrione(通用名)、理有龍(linuron)、碸嘧磺隆(rimsulfuron)、環草定(lenacil)、2,2,2-三氯乙酸(TCA)(包含鈉、鈣或銨等鹽)、2,3,6-三氯苯甲酸(2,3,6-TBA)、2,4,5-三氯苯氧基乙酸(2,4,5-T)、2,4-二氯苯氧基乙酸(2,4-D)(包含胺、二乙胺、三乙醇胺、異丙胺、鈉或鋰等鹽)、2-胺基-3-氯-1,4-萘醌(ACN)、2-甲基-4-氯苯氧基乙酸(MCPA)(包含鈉鹽、乙基酯等)、2-甲基-4-氯苯氧基丁酸(MCPB)(包含鈉鹽、乙基酯等)、4-(2,4-二氯苯氧基)丁酸(2,4-DB)、4,6-二硝基-O-甲酚(DNOC)(包含胺或鈉等鹽)、AE-F-150944(編碼序號)、IR-6396(編碼序號)、MCPA硫基乙基(MCPA-thioethyl)、SYP-298(編碼序號)、SYP-300(編碼序號)、S-乙基二丙基硫基胺甲酸酯(EPTC)、S-莫多草(S-metolachlor)、S-9750(編碼序號)、MSMA(MSMA)、HW-02(編碼序號)、NC-653(編碼序號)、S-523(編碼序號)、SL-1201(編碼序號)。 Ioxynil, aclonifen, acrolein, azafenidin, acifluorfen (including sodium and other salts), azimsulfuron, azimsulfuron, Asulam, acetochlor, atrazine, anilofos, amicarbazone, amidosulfuron, amtrole, Aminocyclopyrachlor, aminopyralid, amiprofos-methyl, ametryn, alachlor, alloxydim, cypropyrimidine Alcohol (ancymidol), isouron, different
Figure 108129126-A0202-12-0169-181
Chlorfenone (isoxachlortole), iso
Figure 108129126-A0202-12-0169-182
Isoxaflutole, isoxaben, Isodecylalkoholethoxylate, isoproturon, ipfencarbazone, imazaquin, methyl Imazapic (containing salts such as amine), imazapyr (containing salts such as isopropylamine), imazamethabenz-methyl, imazamox, imazamox (imazamox) imazethapyr), imazosulfuron, indene
Figure 108129126-A0202-12-0169-183
Indaziflam, indanofan, eglinazine-ethyl, esprocarb, ethametsulfuro-methyl, ethalfluralin, sulfathion (ethidimuron), ethoxysulfuron, ethoxyfen-ethyl, ethofumesate, etobenzanid, endothal-disodium, lemethamate (oxadiazon), propyne
Figure 108129126-A0202-12-0170-184
Oxadiargyl,
Figure 108129126-A0202-12-0170-185
Oxaziclomefone, oxasulfuron, oxyfluorfen, oryzalin, orthosulfamuron, orbencarb, oleic acid , Cafenstrole, carfentrazone-ethyl, carbutilate, carbetamide, carbetamide, quizalofop, quizalofop-ethyl, fast Quizalofop-P-ethyl, quizalofop-P-tefuryl, quinoclamine, quinclorac, quinmerac, bensulfuron-methyl (quinmerac) cumyluron), clacyfos, glyphosate (containing sodium, potassium, amine, propylamine, isopropylamine, dimethylamine or trimethylsulfide), glufosinate ) (Including salts such as amine or sodium), glufosinate-P, glufosinate-P-sodium, clethodim, clodinafop-propargyl ), clopyralid, clomazone, chlomethoxyfen, clomeprop, cloransulam-methyl, chloramben, Chloridazon, chlorimuron-ethyl, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, chlorphthalim, Chlorflurenol-methyl, chlorpropham, chlorbromuron, chloroxuron, chlorotoluron, ketospiradox (ketospiradox) (including salts such as sodium, calcium or ammonium), Saflufenacil, sarmentine, cyanazine, cyanamide, diuron, acetochlor (d iethatyl-ethyl), dicamba (containing amine, diethylamine, isopropylamine, diglycolamine, sodium or lithium, etc.), cycloate, cycloxydim, dichlorosulfonate Diclosulam, cyclosulfamuron, cyclopyranil (common name, pyrazole herbicide), cyclopyrimorate (common name), dichlobenil, diclofop-P-methyl, he Diclofop-methyl, 2,4 drops of propionate (dichlorprop), 2,4 drops of propionate-P (dichlorprop-P), diquat (diquat), dithiopyr (dithiopyr), cyclic grass Siduron, dinitramine, cinidon-ethyl, cinosulfuron, dinoseb, dinoterb, cyanogen Cyhalofop-butyl, diphenamid, difenzoquat, diflufenican, diflufenzopyr, simazine, madochlor ( dimethachlor), dimethametryn, dimethenamid, dimethenamid-P, dimethenamid-P, simetryn, dimepiperate,
Figure 108129126-A0202-12-0171-186
Dimefuron, cinmethylin, swip, sulcotrione, sulfentrazone, sulfosate, sulfosulfuron , Sulfometuron-methyl, sethoxydim, terbacil, daimuron, thaxtomin A (common name), dalapon, thiazopyr ), tiafenacil, thiencarbazone (including sodium salts, methyl esters, etc.), tiocarbazil, thiobencarb, thidiazimin, thiophene Thidiazuron, thifensulfuron-methyl, desmedipham, desmetryne, tetflupyrolimet (common name), thenylchlor, thenylchlor, tebutam, special Tebuthiuron, tepraloxydim, tefuryltrione, terbuthylazine, terbutryn, terbumeton, tembotrione , Topramezone (topramezone), oxachlor (tralkoxydim), three
Figure 108129126-A0202-12-0171-187
Triaziflam, triasulfuron, triafamone, tri-allate, trietazine, triclopyr, triclosan (triclopyr-butotyl), tritosulfuron (tritosulfuron), trifludimoxazin (common name), triflusulfuron-methyl (triflusulfuron-methyl), trifluralin (trifluralin), trifloxysulfuron-sodium , Tribenuron-methyl (tribenuron-methyl), tolpyralate (common name), sodium decay (naptalam) (including sodium and other salts), naproanilide (naproanilide), napropamide (napropamide), mesoprote (napropamide-M) , Nicosulfuron, niburon, norflurazon, vernolate, paraquat dichloride, halauxifen-benzyl , Haloxyifen-methyl, haloxyfop, haloxyfop-P, haloxyfop-etotyl, halosafen , Halosulfuron-methyl, bixlozone (bixlozone), picloram, picolinafen, bicyclopyrone, bispyribac-sodium, Pinoxaden, bifenox, piperophos, pyraclonil, pyrasulfotole, pyrazoxyfen, pyrazolone (pyrazoxyfen) pyrazosulfuron-ethyl, pyrazolynate, bilanafos, pyraflufen-ethyl, pyridafol, pyrithiobac-sodium, pygall ( pyridate), pyriftalid, pyributicarb, pyribenzoxim, pyrimis ulfan (common name), pyriminobac-methyl, pyroxasulfone, pyroxasulfone, pyroxsulam, phenisopham, fenuron, fenoxasulfone (fenoxasulfone) common name),
Figure 108129126-A0202-12-0172-188
Fenoxaprop (containing methyl, ethyl, isopropyl ester), refined
Figure 108129126-A0202-12-0172-189
Fenoxaprop-P (containing methyl, ethyl, isopropyl ester), fenquinotrione (common name), fenthiaprop-ethyl, fenthiaprop-ethyl, fentrazamide, beetin (phenmedipham), butachlor, butafenacil, butamifos, butylate, butenachlor, butralin, butylene Butroxydim, flazasulfuron, flamprop (containing methyl, ethyl, isopropyl ester), flamprop-M (including methyl, ethyl, isopropyl Esters), primisulfuro-n-methyl, fluazifop-butyl, fluazifop-P-butyl, fluazifop-P-butyl, fluazolate, fluometuron ), fluoroglycofe orthoethyl, flucarbazone-sodium, fluchloralin, flucetosulfuron,
Figure 108129126-A0202-12-0173-190
Fluthiacet-methyl, flupyrsulfuro-n-methyl (containing sodium, calcium, or ammonium salts), flufenacet, and flufenacet
Figure 108129126-A0202-12-0173-191
Flufenpyr-ethyl, flupropanate, flupoxame, flumioxazin, flumiclorac-pentyl, flumetsulam , Fluridone, flurtamone, fluroxypyr (including butyl methyl ester, methyl heptyl ester and other esters, sodium, calcium or ammonium and other salts), flurochloridone (flurochloridone ), pretilachlor, procarbazone-sodium, prodiamine, prodiuron, prosulfuron, prosulfocarb, propaquizafop, Propachlor, propazine, propanil, propyzamide, propisochlor, propionate
Figure 108129126-A0202-12-0173-192
Propyrisulfuron, Propham, Profluazol, Prohexadione-calcium, Propoxycarbazone, Propoxycarbazone-sodium, Ring Profoxydim, bromacil, brompyrazon, prometryn, prometon, bromoxynil (including butyric acid, caprylic acid or enanthic acid, etc.) (Ester), bromofenoxim, bromobutide, flosulam, florpyrauxifen, florpyrauxifen-benzyl, hexazinone ) Penthoxamid, benazolin, penoxsulam, heptamaloxyloglucan (heptamaloxyloglucan), beflubutamid, beflubutamid-M, butene Pebulate, pelargonic acid, bencarbazone, pendimethalin, benzfendizone, bensulide, bensulfuron-methyl ), benzobicyclon, benzofenap, bentazone, pentanochlor, pentoxazone, benfluralin, furfur yellow (benfuresate), fosamine, fomesafen, foramsulfuron, forchlorfenuron, 2-methyl-4 chloropropionic acid (mecoprop) (including (Sodium, potassium, isopropylamine, triethanolamine, dimethylamine and other salts), mecoprop-P-potassium, mesosulfuron (including methyl esters and other esters), nitrate Mesotrione, metazachlor,
Figure 108129126-A0202-12-0174-193
Pyrazosulfuron (metazosulfuron), thiazolone (methabenzthiazuron), benzene
Figure 108129126-A0202-12-0174-194
Metamitron,
Figure 108129126-A0202-12-0174-195
Metamifop, metam, disodium methyl arsenate (DSMA), metiozolin (common name), methyldymuron, metoxuron, sulfoxazone (metoxuron) metosulam), metsulfuron-methyl, metobromuron, metobenzuron, metolachlor, metribuzin, mepiquat chloride, Mefenacet, monosulfuron (containing methyl, ethyl, and isopropyl esters), monolinuron, molinate, iodosulfuron, and formazan Iodosulfulon-methyl-sodium, iofensulfuron (iofensulfuron), iofensulfuron-sodium, iofensulfuron-sodium, lactofen, lancotrione (common name), and liyoulong (linuron), rimsulfuron, lenacil, 2,2,2-trichloroacetic acid (TCA) (including sodium, calcium or ammonium salts), 2,3,6-trichloro Benzoic acid (2,3,6-TBA), 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), 2,4-dichlorophenoxyacetic acid (2,4-D ) (Including amine, diethylamine, triethanolamine, isopropylamine, sodium or lithium and other salts), 2-amino-3-chloro-1,4-naphthoquinone (ACN), 2-methyl-4-chlorobenzene Oxyacetic acid (MCPA) (including sodium salt, ethyl ester, etc.), 2-methyl-4-chlorophenoxybutyric acid (MCPB) (including sodium salt, ethyl ester, etc.), 4-(2,4 -Dichlorophenoxy)butyric acid (2,4-DB), 4,6-dinitro-O-cresol (DNOC) (including salts such as amine or sodium), AE-F-150944 (coding serial number) , IR-6396 (coding serial number), MCPA-thioethyl (MCPA-thioethyl), SYP-298 (coding serial number), SYP-300 (coding serial number), S-ethyldipropylthiocarbamate ( EPTC), S-metolachlor, S-9750 (coding serial number), MSMA (MSMA), HW-02 (coding serial number), NC-653 (coding serial number), S-523 (coding serial number) , SL-1201 (coding serial number).

植物生長調節劑： Plant Growth Regulator:

1-萘基乙醯胺(1-naphthylacetamide)、1-甲基環丙烯(1-methylcyclopropene)、2,6-二異丙基萘(2,6-diisopropylnaphthalene)、4-側氧基-4-(2-苯基乙基)胺基丁酸(化學名，CAS登錄號碼：1083-55-2)、4-氯苯氧基乙酸(4-CPA)、正癸醇(n-decanol)、艾維激素(aviglycine)、嘧啶醇(ancymidol)、離層酸(abscisic acid)、依鈉素(inabenfide)、吲哚乙酸(indole acetic acid)、吲哚丁酸(indole butyric acid)、單克素(uniconazole)、單克 素-P(uniconazole-P)、Ecolyst(Ecolyst)、吲熟酯(ethychlozate)、益收生長素(ethephon)、丙醯芸苔素內酯(epocholeone)、奧辛硫酸鹽(oxine-sulfate)、香旱芹酮(carvone)、甲酸鈣(calcium formate)、坐果酸(cloxyfonac)、坐果酸鉀鹽(cloxyfonac-potassium)、坐果安(cloprop)、克美素(chlormequat)、膽鹼(choline)、細胞***素(cytokinins)、環丙草胺(cyclanilide)、敵草克(dikegulac)、赤黴酸(gibberellin acid)、穫萎得(dimethipin)、殺雄啉(sintofen)、丁醯肼(daminozide)、噻苯隆(thidiazuron)、三十烷醇(triacontanol)、抗倒酯(trinexapac-ethyl)、巴克素(paclobutrazol)、石蠟(paraffin)、氟節胺(flumetralin)、呋嘧醇(flurprimidol)、抑草丁(flurenol)、pronitridine(通用名)、茉莉酸丙酯(prohydrojasmon)、調環酸鈣鹽(prohexadione-calcium)、heptamaloxyloglucan(通用名)、苄胺嘌呤(benzylaminopurine)、氯吡苯脲(forchlorfenuron)、順丁烯二醯肼(maleic hydrazide)、缩節胺(mepiquat chloride)、氟磺醯草胺(mefluidide)、過氧化鈣。 1-naphthylacetamide, 1-methylcyclopropene, 2,6-diisopropylnaphthalene, 4-oxo-4- (2-Phenylethyl)aminobutyric acid (chemical name, CAS registration number: 1083-55-2), 4-chlorophenoxyacetic acid (4-CPA), n-decanol (n-decanol), Ai Aviglycine, ancymidol, abscisic acid, inabenfide, indole acetic acid, indole butyric acid, monogram ( uniconazole), single gram -P (uniconazole-P), Ecolyst (Ecolyst), indyl ester (ethychlozate), ethephon, ethephon, acetolactone (epocholeone), oxine-sulfate (oxine-sulfate), Carvone, calcium formate, cloxyfonac, cloxyfonac-potassium, cloprop, chlormequat, choline, cells Cytokinins, cyclanilide, dikegulac, gibberellin acid, dimethipin, sintofen, daminozide, Thidiazuron, triacontanol, trinexapac-ethyl, paclobutrazol, paraffin, flumetralin, flurprimidol, and Flurenol, pronitridine (generic name), propyl jasmonate (prohydrojasmon), prohexadione-calcium, heptamaloxyloglucan (generic name), benzylaminopurine (benzylaminopurine), forchlorfenuron ), maleic hydrazide, maleic hydrazide, mepiquat chloride, mefluidide, and calcium peroxide.

其次，將可以混合或併用的公知的藥害減輕化合物例示如下。 Next, the known phytotoxicity-reducing compounds that can be mixed or used together are exemplified as follows.

雙苯

Figure 108129126-A0202-12-0176-196
唑酸(isoxadifen)、雙苯
Figure 108129126-A0202-12-0176-197
唑酸乙酯(isoxadifen-ethyl)、解草腈(oxabetrinil)、解毒喹(cloquintcet-mexyl)、增效磷(dietholate)、解草胺腈(cyometrinil)、二氯丙烯胺(dichlormid)、二環酮(dicyclonone)、環丙磺醯胺(cyprosulfamide)、1,8-萘二甲酸酐(1,8-Naphthalic Anhydride)、解草唑(fenchlorazole-O-ethyl)、解草啶(fenclorim)、解草
Figure 108129126-A0202-12-0176-198
唑(furilazole)、氟草肟(fluxofenim)、解草胺 (flurazole)、解草酮(benoxacor)、mephenate(通用名)、吡唑解草酸(mefenpyr)、吡唑解草酸乙酯(mefenpyr-ethyl)、吡唑解草酸二乙酯(mefenpyr-diethyl)、低級烷基取代苯甲酸、2,2-二氯-N-(1,3-二
Figure 108129126-A0202-12-0177-199
烷-2-基甲基)-N-(2-丙烯基)乙醯胺(PPG-1292)、2-二氯甲基-2-甲基-1,3-二
Figure 108129126-A0202-12-0177-200
烷(MG-191)、3-二氯乙醯基-2,2，5-三甲基-1,3-
Figure 108129126-A0202-12-0177-201
唑烷(R-29148)、4-二氯乙醯基-1-氧雜-4-氮雜螺環[4.5]癸烷(AD-67)、MON4660(編碼序號)、metcamifen(通用名)、N1,N2-二烯丙基-N2-二氯乙醯基甘胺醯胺(DKA-24)、TI-35(編碼序號)。 Bisbenzene
Figure 108129126-A0202-12-0176-196
Izodic acid (isoxadifen), bisbenzene
Figure 108129126-A0202-12-0176-197
Isoxadifen-ethyl, oxabetrinil, cloquintcet-mexyl, dietholate, cyometrinil, dichlormid, dicyclo Dicyclonone, cyprosulfamide, 1,8-Naphthalic Anhydride, fenchlorazole-O-ethyl, fenclorim, fenclorim grass
Figure 108129126-A0202-12-0176-198
Furilazole, fluxofenim, flurazole, benoxacor, mephenate (common name), mefenpyr, mefenpyr-ethyl ), mefenpyr-diethyl pyrazolate (mefenpyr-diethyl), lower alkyl substituted benzoic acid, 2,2-dichloro-N-(1,3-di
Figure 108129126-A0202-12-0177-199
Alkan-2-ylmethyl)-N-(2-propenyl)acetamide (PPG-1292), 2-dichloromethyl-2-methyl-1,3-di
Figure 108129126-A0202-12-0177-200
Alkane (MG-191), 3-dichloroacetyl-2,2,5-trimethyl-1,3-
Figure 108129126-A0202-12-0177-201
Oxazolidine (R-29148), 4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67), MON4660 (coding number), metcamifen (common name), N1,N2-diallyl-N2-dichloroacetamideglycamine (DKA-24), TI-35 (coding number).

按照上述所構成的本發明之有害生物防除劑，對於直翅目害蟲、纓翅目害蟲、半翅目害蟲、鞘翅目害蟲、雙翅目害蟲、鱗翅目害蟲、膜翅目害蟲、彈尾目害蟲、衣魚目害蟲、蜚蠊目害蟲、囓蟲目害蟲、食毛目害蟲、蝨目害蟲、植物寄生性蟎類、植物寄生性線蟲類、植物寄生性軟體動物、其他有害動物、令人不舒服的動物、衛生害蟲、寄生蟲等有害生物顯示優異之防除效果。如此的有害生物可例示如下述之生物種。 The pest control agent of the present invention constituted as described above is suitable for orthoptera pests, Thysanoptera pests, hemiptera pests, Coleoptera pests, Diptera pests, Lepidoptera pests, Hymenoptera pests, and Pteroceras pests. , Chlamydomonas pests, Blattidae pests, Rodentes pests, Trichoderma pests, Liceles pests, plant parasitic mites, plant parasitic nematodes, plant parasitic mollusks, other harmful animals, unpleasant Comfortable animals, sanitary pests, parasites and other harmful organisms show excellent control effect. Such pests can be exemplified by the following biological species.

直翅目害蟲例如可舉：螽蟖科之黑頸鉤額螽(Ruspolia lineosa)等；蟋蟀科之閻魔蟋蟀(Teleogryllus emma)、梨片蟋(Truljalia hibinonis)等；螻蛄科之螻蛄(Gryllotalpa orientalis)、蝗蟲科之小翅蝗蟲(Oxya hyla intricate)、東亞飛蝗(Locusta migratoria)、血黑蝗(Melanoplus sanguinipes)、異黑蝗(Melanoplus differentialis)、赤脛黑蝗(Melanoplus femurrubrum)等；背負蝗科之背負蝗(Atractomorpha lata)；松蟲科之茅蟋蟀(Euscyrtus japonicus)；蚤蝗蟲科之日本蚤蝗蟲(Xya japonicus)等。 Orthoptera pests include, for example: Ruspolia lineosa, and other species; Teleogryllus emma, Truljalia hibinonis, etc.; Gryllot pa (Gryllot) , Oxya hyla intricate of the locust family, Locusta migratoria, Melanoplus sanguinipes, Melanoplus differentialis, Melanoplus femurrubrum, etc.; carrying the locust family Carrying locust (Atractomorpha lata); Cricket (Euscyrtus japonicus) of the pine insect family; Japanese flea locust (Xya japonicus) of the flea locust family.

纓翅目害蟲例如可舉：薊馬科之台灣薊馬(Frankliniella intonsa)、西方薊馬(Frankliniella occidentalis)、小黃薊馬(Scirtothrips dorsalis)、南黃薊馬(Thrips palmi)、蔥薊馬(Thrips tabaci)、日本煙草薊馬(Thrips setosus)、變葉木薊馬(Heliothrips haemorrhoidalis)、稻薊馬(Stenchaetothrips biformis)等；管薊馬科之柿管薊馬(Ponticulothrips diospyrosi)、芥辣管薊馬(Liothrips wasabiae)、稻管薊馬(Haplothrips aculeatus)等。 Examples of the Thysanoptera pests are: Thrips Taiwan thrips (Frankliniella intonsa), Western thrips (Frankliniella occidentalis), Small yellow thrips (Scirtothrips dorsalis), Southern yellow thrips (Thrips palmi), Onion thrips (Thrips palmi) Thrips tabaci), Japanese tobacco thrips (Thrips setosus), leaf thrips (Heliothrips haemorrhoidalis), rice thrips (Stenchaetothrips biformis), etc.; persimmon thrips (Ponticulothrips diospyrosi), mustard tube thrips (Liothrips wasabiae), rice tube thrips (Haplothrips aculeatus), etc.

半翅目害蟲例如可舉：蟬科之姬草蟬(Mogannia minuta)等；沫蟬科(Cercopidae)之白帶尖胸沫蟬(Aphrophora intermedia)、甘蔗沬蟬(Mahanarva fimbriolata)等；角蟬科之褐角蟬(Machaerotypus sibiricus)等；葉蟬科之葡萄葉蟬(Arboridia apicalis)、茶小綠葉蟬(Empoasca onukii)、偽黑尾葉蟬(Nephotettix cincticeps)、馬來亞黑尾葉蟬(Nephotettix malayanus)、台灣黑尾葉蟬(Nephotettix virescens)、黑條黑尾葉蟬(Nephotettix nigropictus)、電光紋葉蟬(Recilia dorsalis)、二點小綠葉蟬(Amrasca biguttula)、檬果褐葉蟬(Idioscopus nitidulus、Idioscopus clypealis、Amritodus atkinsoni)、電光紋葉蟬(Recilia dorsalis)、馬鈴薯葉蟬(Empoasca fabae)、玉米葉蟬(Dalbulus maidis)等；菱飛蝨科之菱飛蝨(Pentastiridius apicalis)等；稻蝨科之斑飛蝨(Laodelphax striatellus)、褐飛蝨(Nilaparvata lugens)、白背飛蝨(Sogatella furcifera)、玉米飛蝨(Peregrinus maidis)等；縞飛蝨科之縞飛蝨(Nisia nervosa)等；長翅飛蝨科之砂糖斑長飛蝨(Kamendaka saccharivora)等；小頭飛蝨科之紅黴菌飛蝨(Achilus flammeus)等；廣翅蠟蟬科之鼈甲廣翅蠟蟬(Orosanga japonicus) 等；青翅飛蝨科之禾草褐蛾蠟蟬(Mimophantia maritima)等；木蝨科之梨木蝨(Cacopsylla pyrisuga)、柑橘木蝨(Diaphorina citri)等；榕木蝨科之芒果木蝨(Calophya mangiferae)等；根瘤蚜科之葡萄根瘤蚜(Daktulosphaira vitifoliae)等；球蚜科之落葉松球蚜(Adelges laricis)、鐵杉球蚜(Adelges tsugae)等；蚜科之豌豆蚜(Acyrthosiphon pisum)、棉蚜(Aphis gossypii)、橘捲葉蚜(Aphis spiraecola)、偽菜蚜(Lipaphis erysimi)、菜蚜(Brevicoryne brassicae)、桃紅蚜(Myzus persicae)、麥綠蚜(Schizaphis graminum)、稻麥蚜(Rhopalosiphum padi)、小橘蚜(Toxoptera aurantii)、馬鈴薯長鬚蚜(Aulacorthum solani)、馬鈴薯網管蚜(Macrosiphum euphorbiae)、萵苣衲長管蚜(Nasonovia ribisnigri)、麥長管蚜(Sitobion avenae)、大豆蚜(Aphis glycines)等；粉蝨科之茶刺粉蝨(Aleurocanthus camelliae)、柑桔黑刺粉蝨(Aleurocanthus spiniferus)、煙草粉蝨(Bemisia tabaci)、銀葉粉蝨(Bemisia argentifolii)、溫室粉蝨(Trialeurodes vaporariorum)等；碩介殼蟲科之草履介殼蟲(Drosicha corpulenta)、吹綿介殼蟲(Icerya purchasi)等；粉介殼蟲之鳳梨嫡粉介殼蟲(Dysmicoccus brevipes)、柑桔粉介殼蟲(Planococcus citri)、桑粉介殼蟲(Pseudococcus comstocki)等；介殼蟲科之角蠟介殼蟲(Ceroplastes ceriferus)、紅蠟介殼蟲(Ceroplastes rubens)等；仁介殼蟲科之甘蔗仁介殼蟲(Aclerda takahashii)等；盾介殼蟲科之橘紅腎圓盾介殼蟲(Aonidiella aurantii)、梨齒盾介殼蟲(Diaspidiotus perniciosus)、桑白盾介殼蟲(Pseudaulacaspis pentagona)、矢尖盾介殼蟲(Unaspis yanonensis)等；盲椿象科之美國牧草盲椿象(Lygus lineolaris)、紅鬚細綠盲椿象(Trigonotylus caelestialium)、綠盲椿象(Apolygus lucorum)、煙草盲椿象 (Nesidiocoris tenuis)、庭園盲椿象(Halticus bractatus)等；軍配蟲科之杜鵑軍配蟲(Stephanitis pyrioides)、梨軍配蟲(Stephanitis nashi)等；椿象科之皺紋菜椿象(Eurydema rugosum)、大二星椿象(Eysarcoris lewisi)、二星椿象(Eysarcoris aeneus)、稻椿象(Lagynotomus elongatus)、南方綠椿象(Nezara viridula)、珀椿象(Plautia crossota)、東方稻綠椿象(Nezara antennata)、褐椿象(Euschistus heros)、紅帶月椿象(Piezodorus guildini)、稻椿象(Tibraca limbativentris)、綠苺椿象(Dichelops furcatus)等；圓椿象科之台灣圓椿象(Megacopta cribraria)等；異尾椿象科之梨椿象(Urochela luteovoria)等；長椿象科之甘蔗小翅長椿象(Cavelerius saccharivorus)等；突眼長椿象科之豆突眼長椿象(Malcus japonicus)等；紅椿象科之離斑棉紅椿象(Dysdercus cingulatus)等；蛛緣椿象科之禾蛛緣椿象(Leptocorisa acuta)、中華稻緣椿象(Leptocorisa chinensis)等；緣椿象科之紋鬚同緣椿象(Anacanthocoris striicornis)等；姬緣椿象科之赤姬緣椿象(Rhopalus maculatus)等；土椿象科之褐土椿象(Scaptocoris castanea)等；臭蟲科之溫帶臭蟲(Cimex lectularis)等。 Hemiptera pests include, for example: Mogannia minuta and the like; Aphrophora intermedia of Cercopidae, Acanophora intermedia, Mahanarva fimbriolata, etc.; Brown-horned cicada (Machaerotypus sibiricus), etc.; grape leaf cicada (Arboridia apicalis), tea small green leaf cicada (Empoasca onukii), pseudo black-tailed cicada (Nephotettix cincticeps), Malayan black-tailed cicada (Nephotettix malayanus) ), Taiwan black-tailed leafhopper (Nephotettix virescens), black-striped blacktail leafhopper (Nephotettix nigropictus), electro-optic leafhopper (Recilia dorsalis), two-pointed green leafhopper (Amrasca biguttula), lemon fruit brown leafhopper (Idioscopus nitidulus) , Idioscopus clypealis, Amritodus atkinsoni), Recilia dorsalis, potato leafhopper (Empoasca fabae), corn leafhopper (Dalbulus maidis), etc.; Pentastiridius apicalis, etc.; rice planthopper Laodelphax striatellus, brown planthopper (Nilaparvata lugens), white-backed planthopper (Sogatella furcifera), corn planthopper (Peregrinus maidis), etc.; Nisia nervosa, etc.; long-winged Kamendaka saccharivora of the planthopper family, etc.; Achilus flammeus of the red-headed planthopper family, Achilus flammeus, etc.; Orosanga japonicus Etc.; Mimophantia maritima, etc.; Cacopsylla pyrisuga, Diaphorina citri, etc.; Mango wood lice (Calophya) mangiferae), etc.; Daktulosphaira vitifoliae, etc.; Adelges laricis, Adelges largais, Adelges tsugae, etc.; Acyrthosiphon pisum, cotton Aphis (Aphis gossypii), Aphis spiraecola, Lipaphis erysimi, Vegetable aphid (Brevicoryne brassicae), Myzus persicae, Myzus persicae, Schizaphis graminum, Rice and wheat aphid (Rhopalosiphum) padi), Toxoptera aurantii, Aulacorthum solani, Potato network aphid (Macrosiphum euphorbiae), lettuce genus aphid (Nasonovia ribisnigri), wheat long tube aphid (Sitobion avenae), soybean aphid Aphis glycines), etc.; Aleurocanthus camelliae, Aleurocanthus spiniferus, Bemisia tabaci, Bemisia argentifolii, greenhouse whitefly Trialeurodes vaporariorum); Drosicha corpulenta, Icerya purchasi, etc.; Dysmicoccus brevipes, Planococcus citri ), mulberry scale insects (Pseudococcus comstocki), etc.; Ceroplastes ceriferus, Ceroplastes rubens, etc.; Sugarcane scale insects (Aclerda takahashii), etc.; Orange-red kidney round shield shell insect (Aonidiella aurantii) and pear-toothed shell insect (Diaspidiotus) perniciosus), Pseudaulacaspis pentagona, Unaspis yanonensis, etc.; Lygus lineolaris, Trigonotylus caelestialium, green blind Stink bug (Apolygus lucorum), tobacco blind stink bug (Nesidiocoris tenuis), garden blind stink bugs (Halticus bractatus), etc.; junior worms (Stephanitis pyrioides), pear army worms (Stephanitis nashi), etc.; Eurydema rugosum, big two-star stink bugs Eysarcoris lewisi), two-star stink bug (Eysarcoris aeneus), rice stink bug (Lagynotomus elongatus), southern green stink bug (Nezara viridula), perch stink bug (Plautia crossota), oriental rice stink bug (Nezara antennata), brown stink bug (Euschistus heros), red Piezodorus guildini, Tibraca limbativentris, Dichelops furcatus, etc.; Megacopta cribraria of Taiwan's round torus, Megaropta cribraria, etc.; Urochela luteovoria, etc.; The sugarcane small-winged stink bug (Cavelerius saccharivorus) of the elephantae family; Malcus japonicus, etc.; Dysdercus cingulatus of the red stink bug (Dysdercus cingulatus); arachnids Branches of the family Liptocorisa acuta, Leptocorisa chinensis, etc.; Anacanthocoris striicornis, etc.; Rhopalus maculatus, etc. ; Cinex lectularis (Cimex lectularis), etc.;

鞘翅目害蟲例如可舉：金龜子科之銅色麗金龜(Anomara cuprea)、紅銅麗金龜(Anomara rufocuprea)、豆金龜(Popillia japonica)、小青花金龜(Oxycetonia jucunda)、櫻桃小麗金龜(Anomala geniculata)、椰子犀角金龜(Oryctes rhinoceros)、茶色長金龜(Heptophylla picea)、六月金龜(Phyllophaga cuyabana)等；叩頭蟲科之鳶色細胸叩頭蟲(Agriotes ogurae)、直條叩頭蟲(Agriotes lineatus)、暗色叩頭蟲(Agriotes obscurus)、沖繩梳爪叩頭蟲(Melanotus okinawensis)、圓首梳爪叩頭蟲(Melanotus fortnumi)等；鰹節蟲科之姬圓鰹節蟲(Anthrenus verbasci)等；長蠹蟲科之二突異翅長蠹蟲(Heterobostrychus hamatipennis)等；食骸蟲科之藥材甲蟲(Stegobium paniceum)等；蛛甲科之棕蛛甲(Pitinus clavipes)等；穀盜蟲科之大穀盜(Tenebroides mauritanicus)等；郭公蟲科之赤足郭金蟲(Necrobia rufipes)；出尾蟲科之黃斑露尾甲(Carpophilus hemipterus)、油菜花露尾甲(Meligethes seneus)等；細扁蟲科之背圓粉扁蟲(Ahasverus advena)等；姬扁蟲科之角胸粉扁蟲(Cryptolestes ferrugineus)等；瓢蟲科之墨西哥豆瓢蟲(Epilachna varivestis)、茄二十八星瓢蟲(Henosepilachna vigintioctopunctata)等；擬步行蟲科之黃粉蟲(Tenebrio molitor)、擬穀盜(Tribolium castaneum)等；芫菁科之豆莞菁(Epicauta gorhami)等；天牛科之光肩星天牛(Anoplophora glabripennis)、葡萄虎天牛(Xylotrechus pyrrhoderus)、松斑天牛(Monochamus alternatus)、大豆黑光天牛(Dectes texanus)等；豆象科之綠豆象(Callosobruchus chinensis)等；金花蟲科之科羅拉多金花蟲(Leptinotarsa decemlineata)、西方玉米根蟲(Diabrotica virgifera virgifera)、北方玉米根蟲(Diabrotica barberi)、南方玉米根蟲(Diabrotica undecimpunctata howardi)、黃守瓜(Aulacophora femoralis)、甘藍金花蟲(Phaedon brassicae)、甜菜大龜甲(Cassida nebulosa)、水稻負泥蟲(Oulema oryzae)、墨西哥大豆瓢蟲(Epilachna varivestis)、黃條葉蚤(Phyllotreta striolata)、茶肖葉甲(Demotina fasciculata)、油菜金頭跳甲(Psylliodes chrysocephala)、菜豆黃跳甲(Cerotoma trifurcate)、葡萄肖跳甲(Colaspis brunnea)、愛荷華肖跳甲(Colaspis crinnicornis)、大豆跳甲(Odontota horni)、玉米跳甲(Chaetocnema pulicaria)、帶斑黃瓜葉甲 (Diabrotica balteata)等；三維象蟲科之甘藷蟻象(Cylas formicarius)等；象鼻蟲科之苜蓿葉象鼻蟲(Hypera postica)、蔬菜象蟲(Listroderes costirostris)、甘藷象鼻蟲(Euscepes postfasciatus)、栗象鼻蟲(Curculio sikkimensis)、墨西哥棉鈴象鼻蟲(Anthonomus grandis)、豆莖象鼻蟲(Sternechus subsignatus)等；稻象鼻蟲科之二星稻象(Echinocnemus bipunctatus)、稻根象鼻蟲(Lissorhoptrus oryzophilus)、南美稻象鼻蟲(Oryzophagus oryzae)等；椰象鼻蟲科之玉米象鼻蟲(Sitophilus zeamais)、芝隱喙象鼻蟲(Sphenophorus venatus)、甘蔗象鼻蟲(Sphenophorus levis)等；木蠹蟲科之縱坑切梢小蠹(Tomicus piniperda)等；長小蠹蟲科之臺日截尾長小蠹(Crossotarsus niponicus)等；粉蠹科之褐粉蠹(Lyctus brunneus)等。 Coleoptera pests include, for example: Anomara cuprea (Anomara cuprea), red copper beetle (Anomara rufocuprea), bean chafer (Popillia japonica), blue-and-white chafer (Oxycetonia jucunda), cherry chamomile (Anomala geniculata) ), coconut rhinoceros chafer (Oryctes rhinoceros), brown chafer (Heptophylla picea), June chafer (Phyllophaga cuyabana), etc.; Agriotes ogurae, Agriotes ogurae, Agriotes lineatus, Dark-colored beetle (Agriotes obscurus), Okinawa comb-clawed beetle (Melanotus okinawensis), round-headed comb-clawed beetle (Melanotus) fortnumi), etc.; Anthrenus verbasci, etc.; Heterobostrychus hamatipennis, etc.; Stegobium paniceum, etc.; Arachnidae Pitinus clavipes, etc.; Tenebroides mauritanicus, etc.; Necrobia rufipes, Guopoidae; Carpophilus hemipterus 、Meligethes seneus, etc.; Ahasverus advena, etc.; Cryptolestes ferrugineus, etc.; Mexican beans of Coccinellidae Ladybug (Epilachna varivestis), eggplant twenty-eight star ladybug (Henosepilachna vigintioctopunctata), etc.; Tenebrio molitor, Tribolium castaneum, etc.; Beans of the family Corolla Epicauta gorhami), etc.; Anoplophora glabripennis, Xylotrechus pyrrhoderus, Monochamus alternatus, Dectes texanus, etc.; Mung bean like Leguminosae Callosobruchus chinensis), etc.; Colorado golden bug (Leptinotarsa decemlineata), western corn rootworm (Diabrotica virgifera virgifera), northern corn rootworm (Diabrotica barberi), southern corn rootworm (Diabrotica undecimpunctata howardi), Huang Shou Melon (Aulacophora femoralis), Brassica brassicae (Phaedon brassicae), beet beetle (Cassida nebulosa), rice negative mudworm (Oulema oryzae), Mexican soybean ladybug (Epilachna varivestis), yellow stripe fleas (Phyllotreta striolata), Teatina leaf beetle (Demotina fasciculata), rapeseed golden-headed beetle (Psylliod es chrysocephala), Cerotoma trifurcate, Colaspis brunnea, Colaspis crinnicornis, Odontota horni, Chaetocnema pulicaria, belt Cucumber leaf beetle (Diabrotica balteata), etc.; three-dimensional weevil family of sweet potato ant elephant (Cylas formicarius), etc.; weevil family of alfalfa leaf weevil (Hypera postica), vegetable weevil (Listroderes costirostris), sweet potato weevil (Euscepes postfasciatus ), chestnut weevil (Curculio sikkimensis), Mexican cotton boll weevil (Anthonomus grandis), bean stem weevil (Sternechus subsignatus), etc.; Echinocnemus bipunctatus, rice root weevil Insects (Lissorhoptrus oryzophilus), South American rice weevils (Oryzophagus oryzae), etc.; Coco weevil corn corn weevils (Sitophilus zeamais), Zhibei beak weevils (Sphenophorus venatus), sugarcane weevils (Sphenophorus levis ), etc.; Tomicus piniperda, the longitudinal pit-cutting bark of the wood codidae; Crossotarsus niponicus, etc.; Lyctus brunneus, etc. of the powder codidae.

雙翅目害蟲例如可舉：大蚊科之切蛀大蚊(Tipula aino)等；毛蚋科之毛蚋(Plecia nearctica)等；蕈蚋科之香菇蚋(Exechia shiitakevora)等；黑翅蕈蚋科之馬鈴薯黑翅蕈蚋(Pnyxia scabiei)、矮黑翅蕈蚋(Bradysia agrestis)等；癭蚋科之大豆莢癭蚋(Asphondylia yushimai)、小麥癭蚋(Mayetiola destructor)、藍莓癭蚋(Dasineura oxycoccana)等；蚊科之(埃及斑蚊)(Aedes aegypti)、淡色庫蚊(Culex pipiens pallens)等；蚋科之牛蚋(Simulium takahashii)等；搖蚊科之稻搖蚊(Chironomus oryzae)等；虻科之合瘤斑虻(Chrysops suavis)、牛虻(Tabanus trigonus)等；Syrphidae之灰條球蚜蠅(Eumerus strigatus)等；果實蠅科之東方果實蠅(Bactrocera dorsalis)、日本櫻桃果實蠅(Euphranta japonica)、地中海果實蠅(Ceratitis capitata)等；潛葉蠅科之非洲菊斑潛葉蠅(Liriomyza trifolii)、蔬菜斑潛葉 蠅(Liriomyza sativae)、稻潛葉蠅(Agromyza oryzae)、茄斑潛葉蠅(Liriomyza bryoniae)、韭菜葉蠅(Chromatomyia horticola)、蔥潛葉蠅(Liriomyza chinensis)、南美斑潛蠅(Liriomyza trifolii)等；杆蠅科之麥杆蠅(Meromyza nigriventris)等(果蠅科)之斑翅果蠅(Drosophila suzukii)、黑腹果蠅(Drosophila melanogaster)等；水蠅科之(稻小潛葉蠅)(Hydrellia griseola)等；蝨蠅科之馬蝨蠅(Hippobosca equina)等；糞蠅科之笹川糞蠅(Parallelpmma sasakawae)等；花蠅科之蔥地種蠅(Delia antiqua)、灰地種蠅(Delia platura)等；廁蠅科之廁蠅(Fannia canicularis)等；家蠅科之家蠅(Musca domestica)、螫蠅(Stomoxys calcitrans)等；肉蠅科之肉蠅(Sarcophaga peregrina)等；馬蠅科之馬蠅(Gasterophilus intestinalis)等；牛蠅科之牛蠅(紋皮蠅)(Hypoderma lineatum)等；羊蠅科之羊蠅(Oestrus ovis)等。 Diptera pests include, for example: Tipula aino, etc.; Plecia nearctica, etc.; Exechia shiitakevora, etc.; Black-winged fungus Pnyxia scabiei, Bradysia agrestis, etc.; Asphondylia yushimai, Mayetiola destructor, and Dasineura oxycoccana ), etc.; Aedes aegypti, Culex pipiens pallens, etc.; Simulium takahashii, etc.; Chironomus oryzae, etc.; Chrysops suavis, Tabanus trigonus, etc.; Eumerus strigatus, Syrphidae, etc.; Bactrocera dorsalis, Euphranta, Japanese fruit fly japonica), Mediterranean fruit fly (Ceratitis capitata), etc.; Liriomyza trifolii, Liriomyza trifolii Liriomyza sativae, Agromyza oryzae, Liriomyza bryoniae, Chromatomyia horticola, Liriomyza chinensis, Liriomyza trifolii Etc.; Drosophila suzukii (Drosophila suzukii), Drosophila melanogaster etc. (Meromyza nigriventris) and Drosophila melanogaster etc. (Hydrellia griseola), etc.; Hippobosca equina, etc.; Parallelpmma sasakawae, etc.; Delia antiqua, Grey land fly Delia platura), etc.; Fannia canicularis, etc.; Musca domestica, Stomoxys calcitrans, etc.; Sarcophaga peregrina, etc.; Horsefly Horsefly of the family (Gasterophilus intestinalis), etc.; Bovine fly (Hypoderma lineatum) of the family Bovididae (Hypoderma lineatum), etc.; Oestrus ovis of the family Muscidae, etc.

鱗翅目害蟲例如可舉：蝠蛾科之淡緣蝠蛾(Endoclita excrescens)等；艷小蛾科之葡萄艶小蛾(Antispila ampelopsia)等；木蠹蛾科之六星黑點蠹蛾(Zeuzera leuconotum)、姬木蠹蛾(Cossus insularis)等；捲葉蛾科之角紋黃捲葉蛾(Archips fuscocupreanus)、蘋果角紋黃捲葉蛾(Adoxophyes orana fasciata)、梨小喰心蟲(Grapholitha molesta)、茶捲葉蛾(Homona magnanima)、大豆喰心蟲(Leguminivora glycinivorella)、蘋果蠹蛾(Cydia pomonella)、葡萄花翅小捲蛾(Lobesia botrana)等；細葉捲蛾科之葡萄細葉捲蛾(Eupoecilia ambiguella)等；蓑蛾科之黑艷蓑蛾(Bambalina sp.)、微型大蓑蛾(Eumeta minuscula)等；蕈蛾科之穀蛾(Nemapogon granella)、衣蛾(Tinea translucens)等；稜巢蛾科之梨矮蛾 (Bucculatrix pyrivorella)等；潛葉蛾科之桃潛葉蛾(Lyonetia clerkella)、銀紋潛葉蛾(Lyonetiaprunifoliella malinella)等；細蛾科之茶細蛾(Caloptilia theivora)、金紋細蛾(Phyllonorycter ringoniella)等；小潛葉蛾科之柑橘潛葉蛾(Phyllocnistis citrella)等；偽菜蛾科之蔥葉蛾(Acrolepiopsis sapporensis)等；菜蛾科之小菜蛾(Plutella xylostella)；巢蛾科之蘋果巢蛾(Yponomeuta orientalis)等；銀蛾科之蘋果銀蛾(Argyresthia conjugella)等；透翅蛾科之葡萄透翅蛾(Nokona regalis)、蘋果透翅蛾(Synanthedon hector)等；旋蛾科之馬鈴薯麥蛾(Phthorimaea operculella)、麥蛾(Sitotroga cerealella)、棉紅鈴麥蛾(Pectinophora gossypiella)、番茄葉牙蛾(Tuta absoluta)等；果蛀蛾科之(桃蛀果蛾)(Carposina sasakii)等；斑蛾科之梨葉斑蛾(Illiberis pruni)等；刺蛾科之黃刺蛾(Monema flavescens)等；草螟科之日本巢草螟(Ancylolomia japonica)、二化螟(Chilo suppressalis)、稻緃卷葉野螟(Cnaphalocrocis medinalis)、亞洲玉米蛾(Ostrinia furnacalis)、菜心蛾(Hellulla undalis)、桃胡麻斑野螟蛾(Conogethes punctiferlis)、(瓜絹野螟)(Diaphania indica)、早熟禾擬睛草螟(Parapediasia teterrella)、歐洲玉米螟(Ostrinia nubilalis)等；甘蔗桿草螟(Diatraea saccharalis)、螟蛾科之粉斑螟蛾(Cadra cautella)、蠟螟(Galleria mellonella)等；羽蛾科之葡萄羽蛾(Nippoptilia vitis)等；鳳蝶科之柑橘鳳蝶(Papilio xuthus)等；粉蝶科之白紋蝶(Pieris rapae)等；弄蝶科之稻弄蝶(Parnara guttata)等；尺蛾科之腎斑尺蛾(Ascotis selenaria)等；枯葉蛾科之赤松毛蟲(Dendrolimus spectabilis)、帶枯葉蛾(Malacosoma neustrium testaceum)等；天蛾科之蝦殼天蛾(Agrius convolvuli)等；毒蛾科之茶毒蛾(Arna pseudoconspersa)、 小白蚊毒蛾(Orygia recens approximans)、(舞毒蛾)(Lymantria dispar)等；燈蛾科之美國白蛾(Hyphantria cunea)等；夜蛾科之小地老虎(Agrotis ipsilon)、黃地老虎(Agrotis segetum)、黑點銀紋夜蛾(Autographa nigrisigna)、棉鈴實夜蛾(Helicoverpa armigera)、玉米蛾(Helicoverpa zea)、煙草芽夜蛾(Heliothis virescens)、甜菜斜紋夜蛾(Spodoptera exigua)、斜紋夜蛾(Spodoptera litura)、大豆尺蠖(Chrysodeix includens)、草地夜蛾(Spodoptera frugiperda)、銅色切夜蛾(Nephelodes minians)等。 For example, Lepidoptera pests include: Endoclita excrescens of the family Helicopteridae; Antispila ampelopsia, etc.; Six-star black spot moth (Zeuzera leuconotum) ), Cossus insularis, etc.; Archips fuscocupreanus, Adoxophyes orana fasciata, Grapholitha molesta, Homona magnanima ), Soybean heartworm (Leguminivora glycinivorella), apple codling moth (Cydia pomonella), grape flower winged small roller moth (Lobesia botrana), etc.; grape leaf moth (Eupoecilia ambiguella), etc.; Bambalina sp., Eumeta minuscula, etc.; Nemapogon granella, Tinea translucens, etc.; pear dwarf moths (Bucculatrix pyrivorella), etc.; Lyonetia clerkella, Lyonetia prunifoliella malinella, etc.; Caloptilia theivora, Phylonorycter ringoniella Etc.; Phyllocnistis citrella, etc.; Acrolepiopsis sapporensis, etc.; Plutella xylostella; Plutella xylostella; apple nest moth (Yponomeuta orientalis), etc.; Argyresthia conjugella, etc.; Nokona regalis, Synanthedon hector, etc.; Potato wheat moth (Phthorimaea operculella), wheat moth (Sitotroga cerealella), cotton red bell wheat moth (Pectinophora gossypiella), tomato leaf tooth moth (Tuta absoluta), etc.; fruit moth family (Peach borer fruit moth) (Carposina sasakii), etc.; spot Illiberis pruni, etc.; Monema flavescens, etc.; Ancylolomia japonica, Chilo suppressalis, rice curl Leaf moth (Cnaphalocrocis medinalis), Asian corn moth (Ostrinia furnacalis), cabbage moth (Hellulla undalis), peach flax moth (Conogethes punctiferlis), (Diaphania indica), bluegrass Grass worm (Parapediasia teterrella), European corn borer (Ostrinia nubilalis), etc.; Sugarcane stem borer (Diatraea saccharalis), meal moth (Cadra cautella), wax moth (Galleria mellonella), etc.; Grape feather moth (Nippoptilia vitis), etc.; Papilio xuthus (Papilio xuthus), etc.; Pieris rapae (Pieris rapae), etc.; Nymphalidae Parnara guttata, etc.; Ascotis selenaria, etc.; Dendrolimus spectabilis, Malacosoma neustrium testaceum, etc.; Shrimp Shell hawk moth (Agrius convolvuli), etc.; tea poison moth (Arna pseudoconspersa), Orygia recens approximans, Lymantria dispar, etc.; Hyphantria cunea, etc.; Agrotis ipsilon, Agrotis segetum), Autographa nigrisigna, Helicoverpa armigera, corn moth (Helicoverpa zea), Heliothis virescens, Heliothis virescens, Spodoptera exigua, Spodoptera exigua Moth (Spodoptera litura), soybean inchworm (Chrysodeix includens), Spodoptera frugiperda, Nephelodes minians, etc.

膜翅目例如可舉：三節葉蜂科之玫瑰三節葉蜂(Arge pagana)等；葉蜂科之栗葉蜂(Apethymus kuri)、蕪菁葉蜂(Athalia rosae ruficornis)等；癭蜂科之板栗癭蜂(Dryocosmus kuriphilus)等；胡蜂科之黃色胡蜂(Vespa simillima xanthoptera)等；蟻科之入侵紅火蟻(Solenopsis invicta)、阿根廷蟻(Linepithema humile)等；切葉蟻科之薔薇切葉蟻(Megachile nipponica)等。 Examples of Hymenoptera include: Arge pagana and other three species: Apethymus kuri, Athalia rosae ruficornis, etc.; Chestnut gall in the family Meloididae Bees (Dryocosmus kuriphilus), etc.; Vespa simillima xanthoptera, etc.; Solenopsis invicta, Linepithema humile, etc.; Megachile nipponica )Wait.

彈尾目害蟲例如可舉：圓跳蟲科之黃星圓跳蟲(Bourletiella hortensis)等。 For example, the Collembola pests include Bourletiella hortensis and the like.

纓尾目害蟲例如可舉：衣魚科之(衣魚)(Lepisma saccharina)、絨毛衣魚(Ctenolepisma villosa)等。 Examples of tassel-tailed pests include Lepisma saccharina and Ctenolepisma villosa.

蜚蠊目害蟲例如可舉：蜚蠊科之美洲家蠊(Periplaneta americana)；姬蜚蠊科之德國姬蜚蠊(Blattella germanica)；白蟻科之台灣白蟻(Odontotermes formosanus)；木白蟻科科之小楹白蟻(Incisitermes minor)、截頭堆砂白蟻(Cryptotermes domesticus)；溝頭白蟻科之家白蟻(Coptotermes formosanus)、大和白蟻(Reticulitermes speratus)等。 Examples of pests in the order Blattella include: Periplaneta americana in the family Blattella; Blattella germanica in the family Blattella germanica; Odontotermes formosanus in the termite family; Incisitermes minor, Cryptotermes domesticus; Coptotermes formosanus, Reticulitermes speratus, etc.

囓蟲目害蟲例如可舉：節嚙蟲科之粉茶柱蟲(Trogium pulsatorium)等；書蝨科之淡黑書蝨(Liposcelis corrodens)等。 Pests of the order Rodentia include, for example, Trogium pulsatorium of the family Rodentia; Liposcelis corrodens of the family Leptidae.

革翅目害蟲例如可舉：大蠼螋蟲科之大蠼螋蟲(Labodura riparia)等。 Examples of the pests of the order Lepidoptera include Labodura riparia and the like.

食毛目害蟲例如可舉：短角鳥蝨科之雞長羽蝨(Menopon pallidum)等；畜翅蝨科之牛羽蝨(Damalinia bovis)等。 Examples of the insects of the order Trichophyta include: Menopon pallidum of the short-horned bird lice family; Damalia bovis of the family Lepidoptera.

蝨目害蟲例如可舉：畜蝨科之豬血蝨(Haematopinus suis)等；人蝨科之人蝨(Pediculus humanus)等；畜毛蝨科之犬毛蝨(Linognathus setosus)等；毛蝨科之陰蝨(Pthirus pubis)等。 Examples of lice-order pests include: Haematopinus suis, etc.; Pediculus humanus, etc.; Linognathus setosus, etc.; Pthirus pubis, etc.

壁蝨目害蟲例如可舉：走蟎科之麥大背肚蟎(Penthaleus major)等；塵蟎科之仙克來塵蟎(Phytonemus pallidus)、茶塵蟎(Polyphagotarsonemus latus)等；蒲蟎科之一種蒲蟎(Siteroptes sp.)等；偽葉蟎科之葡萄短鬚蟎(Brevipalpus lewisi)等；杜克葉蟎科之孔雀杜克葉蟎(Tuckerella pavoniformis)等；葉蟎科之杏葉蟎(Eotetranychus boreus)、柑橘葉蟎(柑桔紅蜘蛛)(Panonychus citri)、(蘋果葉蟎)(Panonychus ulmi)、二點葉蟎(Tetranychus urticae)、神澤葉蟎(Tetranychus kanzawai)等；納氏癭蟎科之松三毛癭蟎(Trisetacus pini)等；節蜱科之桔刺皮節蜱(Aculops pelekassi)、梨銹蜱(Epitrimerus pyri)、柑桔皺葉刺節蜱(Phyllocoptruta oleivora)、番茄刺皮癟蟎(Aculops lycopersici)等；双羽爪節蜱科之假黃楊節蜱(Diptacus crenatae)等；粉蟎科之橢圓食粉蟎(Aleuroglyphus ovatus)、腐食酪蟎(Tyrophagus putrescentiae)、羅賓根蟎(Rhizoglyphus robini)；瓦蟎科之蜜蜂蟹蟎(Varroa jacobsoni)等；皮刺蟎科之雞皮刺蟎(Dermanyssus gallinae)等；巨刺蟎科之林禽刺蟎(Ornithonyssus sylvialum)等；硬蜱科之微小牛蜱(Boophilus microplus)、血紅扇頭蜱(Rhipicephalus sanguineus)、長角血蜱(Haemaphysalis longicornis)等；疥蟎科之疥蟎(Sarcoptes scabiei)等。 Examples of tick insects include: Penthaleus major, etc.; Phytonemus pallidus, Polyphagotarsonemus latus, etc.; one of the family Acaridae Siteroptes sp., etc.; Brevipalpus lewisi, etc.; Tuckerella pavoniformis, etc.; Eotetranychus, Tetranychus boreus), Citrus spider mite (Panonychus citri), (Apple spider mite) (Panonychus ulmi), Tetranychus urticae, Tetranychus kanzawai, etc.; N. gallinae Trisetacus pini, etc.; Aculops pelekassi, Epitrimerus pyri, Phyllocoptruta oleivora, tomato prickly spider mite (Aculops lycopersici), etc.; Diptacus crenatae, etc.; Aleuroglyphus ovatus, Tyrophagus putrescentiae, Rhizoglyphus robini); Varroa jacobsoni, etc.; Dermanyssus gallinae), etc.; Ornithonyssus sylvialum, etc.; Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, etc.; Sarcoptes scabiei and others.

植物寄生性線蟲類例如可舉：長囊亞科(Longidorinae)之劍線蟲(Xiphinema index)等；毛刺科毛刺線蟲屬(Trichodorus)之較小擬毛刺線蟲(Paratrichodorus minor)等；小桿科(Rhabditidae)小桿線蟲屬之一種等；墊刃科(Tylenchidae)之一種野外墊刃屬(Aglenchus sp.)等；錐墊刃科(Tylodoridae)之一種頭刃線蟲屬(Cephalenchus sp.)等；粒線蟲(Anguina)科之草苺芽線蟲(Nothotylenchus acris)、馬鈴薯腐敗線蟲(Ditylenchus destructor)等；腎形線蟲紐帶科(Hoplolaimidae)科之腎形腎臟線蟲(Rotylenchulus reniformis)、雙宫螺旋線蟲(Helicotylenchus dihystera)等；針線蟲科(Paratylenchus)之彎曲短體線蟲(Paratylenchus curvitatus)等；根瘤線蟲科(Meloidogyneae)之南方根瘤線蟲(Meloidogyne incognita)、北方根瘤線蟲(Meloidogyne hapla)、瓜哇根瘤線蟲(Meloidogyne javanica)、哥倫比亞根瘤線蟲(Meloidogyne chitwoodi)、偽哥倫比亞根瘤線虫(Meloidogyne fallax)等；異皮科(Heteroderidae)之馬鈴薯黃金線蟲(Globodera rostochiensis)、馬鈴薯胞囊線蟲(Globodera pallida)、大豆胞囊線蟲(Heterodera glycines)、甜菜胞囊線蟲(Heterodera Schachtii)等；矮化線蟲屬(Terotylenchus)之矮化線蟲(Tylenchorhynchus claytoni)等；平滑墊刃屬(Psilenchus)之平滑墊刃線蟲之一種(Psilenchus sp.)等；環狀線蟲(Chriconemella)科之環紋線蟲的一種(Criconemoides sp.)等；墊刃線蟲科 (Tylenchulidiae)之柑桔根線蟲(Tylenchulus semipenetrans)等；球形線蟲(Spharonema)科之山茶球形線蟲(Sphaeronema camelliae)等；短體科(Pratylenchidae)的柑桔潛根線蟲(Radopholus citrophilus)、香蕉潛根線蟲(Radopholus similis)、偽根腐線蟲(Nacobbus aberrans)、北方根腐線蟲(Pratylenchus penetrans)、南方根腐線蟲(Pratylenchus coffeae)、玉米根腐線蟲(Pratylenchus zeae)、鳳梨根腐線蟲(Pratylenchus brachyurus)等；小齒科(Iotonchidae)之鮑魚菇厚皮病線蟲(Iotonchium ungulatum)等；滑刃科(Aphelenchus)之燕麥真滑刃線蟲(Aphelenchus avenae)等；滑刃總科(Aphelenchoidae)之稻心枯線蟲(Aphelenchoides besseyi)、草苺線蟲(Aphelenchoides fragariae)等；寄生滑刃科(Parasitaphelenchidae)之松材線蟲(Bursaphelenchus xylophilus)等。 Examples of plant-parasitic nematodes include: Xiphinema index of Longidorinae; Paratrichodorus minor, etc. of Trichodorus genus; and Rhabditidae ) One of the genus C. elegans; one of the genus Aglenchus sp. of Tylenchidae; the other of genus Cephalenchus sp. of Tylodoridae; the nematode (Anguina) family of strawberry bud nematodes (Nothotylenchus acris), potato spoilage nematodes (Ditylenchus destructor), etc.; kidney-shaped nematode (Roplolenmidae) family (Rotylenchulus reniformis), double palace spiral nematode (Helicotylenchus dihystera), etc. ; Paratylenchus curvitatus, etc.; Meloidogyne incognita (Meloidogyne incognita), Meloidogyne hapla (Meloidogyne hapla), Meloidogyne javanica (Meloidogyne javanica), Meloidogyne chitwoodi, Meloidogyne fallax, etc.; Globodera rostochiensis, Globodera pallida, Heterodera glycines, Heteroderidae ), beet cyst nematode (Heterodera Schachtii), etc.; dwarf nematode (Tylenchorhynchus claytoni) of the dwarf nematode genus (Terotylenchus); Psilenchus sp., etc. A type of ringworm nematode (Criconemoides sp.) of the family Chriconemella, etc.; pad-nematode family (Tylenchulidiae) citrus root nematode (Tylenchulus semipenetrans), etc.; spherical nematode (Spharonema) family camellia spherical nematode (Sphaeronema camelliae), etc.; short body (Pratylenchidae) citrus root nematode (Radopholus citrophilus), banana root root Nematodes (Radopholus similis), pseudo-root rot nematodes (Nacobbus aberrans), northern root rot nematodes (Pratylenchus penetrans), southern root rot nematodes (Pratylenchus coffeae), corn root rot nematodes (Pratylenchus zeae), pine root rot nematodes (Pratylenchus zeae), pineapple root rot nematodes (Pratylenchus brachyurus) Etc.; Iotonchium ungulatum of Iotonchidae, etc.; Aphelenchus avenae of Aphelenchus, etc.; Rice heart withered of Aphelenchoidae, etc. Nematodes (Aphelenchoides besseyi), Strawberry nematodes (Aphelenchoides fragariae), etc.; Parasitic Slippers (Parasitaphelenchidae) pine wood nematodes (Bursaphelenchus xylophilus), etc.

植物寄生性軟體動物例如可舉：蘋果螺科之福壽螺(Pomacea canaliculata)等；皺足蛞蝓科之皺足蛞蝓(Leavicaulis alte)等；非洲大蝸牛科之非洲大蝸牛(Achatina fulica)等；黏液蛞蝓科之雙線蛞蝓(Meghimatium bilineatum)等；陸地粗貝科之陸地粗貝(Succinea lauta)等；圓盤蝸牛科(Discidae)之淺圓盤螺(Discus pauper)等；琥珀貝科之蝦夷琥珀貝(Zonitoides yessoensis)等；蛞蝓科之黃蛞蝓(Limax flavus)、瓦侖西亞列蛞蝓(Lehmannia valentiana)、網紋野蛞蝓(Deroceras reticulatum)等；鼈甲蝸牛科之播磨蝸牛(Parakaliella harimensis)等；扁蝸牛科之琉球球蝸牛(Acusta despecta sieboldiana)、扁蝸牛(Bradybaena similaris)等。 Examples of plant-parasitic mollusks include: Pomacea canaliculata of the apple snail family; Leavicaulis alte of the sauropoda family; Leavicaulis alte, etc.; Achatina fulica of the African snail family; mucus slugs Branches of Meghimatium bilineatum, etc.; Succinea lauta, etc.; Discus pauper, etc. of Discidae; Amber shell (Zonitoides yessoensis), etc.; Limax flavus, Lehmannia valentiana, Deroceras reticulatum, etc.; Sophia snails (Parakaliella harimensis), etc.; The Ryukyu ball snail (Acusta despecta sieboldiana), flat snail (Bradybaena similaris) and so on.

其他有害動物、令人不舒服的動物、衛生害蟲、家畜害蟲、寄生蟲等之有害生物例如可舉：美國蜊蛄科之美國蜊蛄(Procambarus clarkii)等；等足目(Isopoda)的鼠婦科(Porcellionidae)之糙瓷鼠婦(Porcellio scaber)等；卷殼蟲科之鼠婦(Armadillidium vulgare)等；蚰蜓目(Scutigeromorpha)蚰蜓科(Scutigeridae)的蚰蜓及蜈蚣目之模棘蜈蚣(Scolopendra subspinipes)等之蜈蚣害蟲目；帶馬陸目(Polydesmoidea)奇馬陸科(Paradoxosomatidae)的高雅酸帶馬陸(Oxidus gracilis)等之倍足綱(Diplopoda)害蟲；蜘蛛目姬蜘蛛科之紅背蜘蛛(Theridiidae hasseltii)等；蜘蛛目袋蜘蛛科之日本美女蜘蛛(Chiracanthium japonicum)等、蠍目之土耳其黑肥尾蝎(Androctonus crassicauda)等；線形動物體內寄生蟲之蛔蟲類蛔蟲(Ascaris lumbricoides)等；蟯蟲類(Syphacia sp.)等；絲蟲類班氏絲蟲(Wuchereria bancrofti)等；扁形動物體內寄生蟲之肝吸蟲(Distomum sp.)、衛氏肺吸蟲(Paragonimus westermanii)、橫川肺吸蟲(Metagonimus yokokawai)、日本住血吸蟲(Schistosoma japonicum)、有鉤條蟲(Taenia solium)、無鉤條蟲(Taeniarhynchus saginatus)、包生條蟲屬(Echinococcus sp.)、廣節裂頭條蟲(Diphyllobothrium latum)等。 Other harmful animals, uncomfortable animals, sanitary pests, domestic animal pests, parasites and other harmful organisms can be exemplified by: Procambarus (Procambarus) clarkii), etc.; Porcellio scaber of Isopoda, Porcellionidae, etc.; Armadillidium vulgare, etc.; Scutigeromorpha, Scorpionidae (Scutigeromorpha) Scutigeridae, Scolopendra subspinipes and other centipedes pests; Polydesmoidea with Polydesmoidea, Paradoxosomatidae, and Oxidus gracilis with ip D, Oddus gracilis, etc. ) Pests; Theridiidae hasseltii, etc.; Chiracanthium japonicum, etc.; Andractonus crassicauda, etc.; Linear animals Ascaris lumbricoides, etc.; Syphacia sp., etc.; Wuchereria bancrofti, etc.; Distomum sp. Paragonimus westermanii, Metagonimus yokokawai, Schistosoma japonicum, Taenia solium, Taeniarhynchus saginatus, echinococcidus (Echinococcus sp.), Diphyllobothrium latum, etc.

本發明的有害生物防除劑是對既有的有害生物防除劑獲得抵抗性的，前述例示的有害生物等也表現防除效果。再者，本發明的有害生物防除劑也可對經過基因重組、人工交配等而獲得抗害蟲性、抗病害性、抗除草劑性等特性的植物使用。 The pest control agent of the present invention is resistant to existing pest control agents, and the pests exemplified above also exhibit a control effect. In addition, the pest control agent of the present invention can also be used for plants that have acquired characteristics such as insect resistance, disease resistance, and herbicide resistance through genetic recombination and artificial mating.

本發明的「藉由育種法或基因重組技術而被賦有抗性的植物」意指不僅包含以古典的品種交配而被賦有抗性、以基因重組技術而被賦有抗性，亦包含藉由在至今為止的交配技術中組合分子生物學手法的新育種技術(New Plant Breeding Techniques，NBTs)而被賦有抗性的植物。 新育種技術(NBTs)記載於書籍「來理解新植物育種技術吧」(國際文獻公司，大澤良，江面浩著作)、評論文章「Genome Editing Tools in Plants」(Genes 2017,8,399，Tapan Kumar Mohanta，Tufail Bashir，Abeer Hashem，Elsayed Fathi Abd＿Allah and Hanhong Bae著)等。 The term "plants that are endowed with resistance by breeding methods or gene recombination techniques" in the present invention means not only the resistance given by mating with classical varieties, but also the resistance endowed with genetic recombination techniques. Among the mating technologies so far, new plant breeding techniques (NBTs) combining molecular biology techniques have been given plants that are resistant. New breeding techniques (NBTs) are recorded in the book "Let's understand the new plant breeding techniques" (International Literature Corporation, Ozawa Liang, Jiang Mianhao works), the review article "Genome Editing Tools in Plants" (Genes 2017, 8,399, Tapan Kumar Mohanta, Tufail Bashir, Abeer Hashem, Elsayed Fathi Abd_Allah and Hanhong Bae) and so on.

其次，將本發明化合物的製造方法、製劑方法以及用途在下述的實施例詳細地說明，惟，本發明不受此等實施例的任何限制。此外，本發明化合物的物性值的熔點係利用YANACO製之MP-500V微量熔點測定裝置測定。折射率係使用ATAGO製之ABBE折射計測定。1H NMR譜係使用日本電子製JNM-LA400(400MHz)、JNM-LA300(300MHz)或JNM-ECS300(300MHz)，以四甲基矽烷(TMS)作為內部標準而測定。高分解能質量分析譜(HRMS)係使用Thermo Fisher Scientific製之Q Exactive Focus Hybrid Quadrupole-Orbitrap LC-MS/MS System(ESI，positive mode)測定。 Next, the production method, preparation method, and use of the compound of the present invention will be described in detail in the following examples, but the present invention is not limited by these examples. In addition, the melting point of the physical property value of the compound of the present invention was measured using an MP-500V trace melting point measuring device manufactured by YANACO. The refractive index was measured using an ABBE refractometer manufactured by ATAGO. The 1 H NMR spectrum was measured using JNM-LA400 (400 MHz), JNM-LA300 (300 MHz) or JNM-ECS300 (300 MHz) manufactured by JEOL Ltd., using tetramethylsilane (TMS) as an internal standard. The high resolution energy mass analysis spectrum (HRMS) was measured using a Q Exactive Focus Hybrid Quadrupole-Orbitrap LC-MS/MS System (ESI, positive mode) manufactured by Thermo Fisher Scientific.

再者，在此亦一同記載本發明化合物之製造中間物的製造法。 In addition, the method for producing the intermediate of the compound of the present invention is also described here.

[實施例1] [Example 1]

5-[5-胺基-3-(三氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基-N-(2,2,2-三氟乙基)苯甲醯胺(本發明之化合物號碼：A-0001)的製造 5-[5-Amino-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methyl-N-(2,2,2 -Production of trifluoroethyl) benzamide (the compound number of the present invention: A-0001)

(1)5-胺基-4-氟-2-甲基苯甲酸乙酯的製造 (1) Manufacture of ethyl 5-amino-4-fluoro-2-methylbenzoate

將依據國際公開專利公報WO2009/078481號所記載的方法所製造之4-氟-2-甲基-5-硝基苯甲酸乙酯16.80g(73.95mmol)溶解於乙醇800mL，並加入10%鈀碳1.68g。然後，在氫環境下於室溫下攪拌5小時。反應結束 後以矽藻土過濾反應混合物，並在減壓下濃縮濾液。藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=3：1)精製殘渣，而得到目標物12.20g(產率84%)。 16.80 g (73.95 mmol) of ethyl 4-fluoro-2-methyl-5-nitrobenzoate produced according to the method described in International Publication Patent Publication WO2009/078481 was dissolved in 800 mL of ethanol, and 10% palladium was added Carbon 1.68g. Then, it was stirred at room temperature for 5 hours under a hydrogen atmosphere. End of reaction The reaction mixture was then filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 3:1) to obtain 12.20 g of the target product (yield 84%).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：1.37(3H,t),2.48(3H,s),3.66(2H,brs),4.32(2H,q),6.85(1H,d),7.41(1H,d) 1 H-NMR data (400MHz, CDCl 3 /TMS δ (ppm)): 1.37 (3H, t), 2.48 (3H, s), 3.66 (2H, brs), 4.32 (2H, q), 6.85 (1H, d), 7.41 (1H, d)

(2)4-氟-5-肼基-2-甲基苯甲酸乙酯的製造 (2) Manufacture of ethyl 4-fluoro-5-hydrazino-2-methylbenzoate

使5-胺基-4-氟-2-甲基苯甲酸乙酯24.45g(124.0mmol)懸浮於濃鹽酸100mL，在冰冷下於0至5℃滴入於30mL的水中溶解有亞硝酸鈉9.41g(136mmol)之水溶液。然後於滴入結束後，一面保持在同一溫度一面攪拌1小時。將於濃鹽酸100mL中溶解有氯化錫47.02g(247.9mmol)之溶液一面保持在同一溫度一面緩慢地滴入於前述反應混合物，並進一步於室溫下攪拌2小時。反應結束後添加乙酸乙酯，藉由氫氧化鈉水溶液進行中和並以矽藻土過濾不溶物。水洗有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由正己烷洗淨所得到之粗生成物，而得到目標物20.48g(產率78%)。 24.45 g (124.0 mmol) of ethyl 5-amino-4-fluoro-2-methylbenzoate was suspended in 100 mL of concentrated hydrochloric acid, and was dropped into 30 mL of water under ice cooling at 0 to 5° C. Dissolved sodium nitrite 9.41 g (136 mmol) in water. Then, after completion of the dropping, the mixture was stirred at the same temperature for 1 hour. A solution of 47.02 g (247.9 mmol) of tin chloride dissolved in 100 mL of concentrated hydrochloric acid was slowly dropped into the aforementioned reaction mixture while maintaining the same temperature, and further stirred at room temperature for 2 hours. After the reaction was completed, ethyl acetate was added, neutralized with an aqueous sodium hydroxide solution, and the insoluble matter was filtered through celite. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting crude product was washed with n-hexane to obtain 20.48 g of the target product (yield 78%).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：1.39(3H,t),2.50(3H,s),3.59(2H,brs),4.35(2H,q),5.34(1H,brs),6.85(1H,d),7.66(1H,d) 1 H-NMR data (400MHz, CDCl 3 /TMS δ (ppm)): 1.39 (3H, t), 2.50 (3H, s), 3.59 (2H, brs), 4.35 (2H, q), 5.34 (1H, brs), 6.85 (1H, d), 7.66 (1H, d)

(3)4-氟-2-甲基-5-[2-(2,2,2-三氟亞乙基)肼基]苯甲酸乙酯的製造 (3) Production of ethyl 4-fluoro-2-methyl-5-[2-(2,2,2-trifluoroethylene)hydrazino]benzoate

將4-氟-5-肼基-2-甲基苯甲酸乙酯10.00g(47.12mmol)、三氟乙醛乙基半縮醛10.18g(70.65mmol)、對甲苯磺酸一水合物0.41g(2.2mmol)及乙醇 70mL之混合物加熱迴流4.5小時。於室溫下放置冷卻後，於減壓下濃縮所得到之反應混合物而得到粗製目標物。不進行精製而直接使用在下一步驟。 Ethyl 4-fluoro-5-hydrazino-2-methylbenzoate 10.00g (47.12mmol), trifluoroacetaldehyde ethyl hemiacetal 10.18g (70.65mmol), p-toluenesulfonic acid monohydrate 0.41g (2.2mmol) and ethanol The 70 mL mixture was heated to reflux for 4.5 hours. After leaving to cool at room temperature, the resulting reaction mixture was concentrated under reduced pressure to obtain a crude target. It is used directly in the next step without purification.

(4)5-[2-(1-溴-2,2,2-三氟伸乙基)肼基]-4-氟-2-甲基苯甲酸乙酯的製造 (4) Production of ethyl 5-[2-(1-bromo-2,2,2-trifluoroethylidene)hydrazino]-4-fluoro-2-methylbenzoate

將粗製的4-氟-2-甲基-5-[2-(2,2,2-三氟伸乙基)肼基]苯甲酸乙酯溶解於N,N-二甲基甲醯胺35mL，在冰冷下於0至5℃添加N-溴琥珀醯亞胺8.55g(48.0mmol)，一面保持在同一溫度一面攪拌1小時。反應結束後添加水並以乙酸乙酯來萃取，藉由飽和食鹽水洗淨所得到之有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑而得到粗製目標物。不進行精製而直接使用在下一步驟。 Dissolve crude ethyl 4-fluoro-2-methyl-5-[2-(2,2,2-trifluoroethylidene)hydrazino]benzoate in 35 mL of N,N-dimethylformamide Under ice cooling, 8.55 g (48.0 mmol) of N-bromosuccinimide was added at 0 to 5° C., and the mixture was stirred at the same temperature for 1 hour. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a crude target. It is used directly in the next step without purification.

(5)5-[5-胺基-3-(三氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸乙酯(本發明之化合物號碼：C-0002)的製造 (5) 5-[5-Amino-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methylbenzoic acid ethyl ester (this Invention compound number: C-0002)

於室溫下將三乙胺14.30g(141.3mmol)添加至粗製的5-[2-(1-溴-2,2,2-三氟伸乙基)肼基]-4-氟-2-甲基苯甲酸乙酯、S-甲基異硫脲碘化氫鹽15.41g(70.67mmol)及四氫呋喃140mL之混合物，然後加熱迴流3小時。於室溫下放置冷卻後，於減壓下濃縮反應混合物，將水添加至殘渣並以乙酸乙酯進行萃取，藉由飽和食鹽水洗淨所得到之有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由正己烷與二異丙醚洗淨所得到之粗生成物，而得到目標物11.63g(產率74%，3步驟)。 At room temperature, 14.30 g (141.3 mmol) of triethylamine was added to the crude 5-[2-(1-bromo-2,2,2-trifluoroethylidene)hydrazino]-4-fluoro-2- A mixture of 15.41 g (70.67 mmol) of ethyl methylbenzoate, S-methylisothiourea hydrogen iodide and 140 mL of tetrahydrofuran was then heated to reflux for 3 hours. After leaving to cool at room temperature, the reaction mixture was concentrated under reduced pressure, water was added to the residue and extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting crude product was washed with n-hexane and diisopropyl ether to obtain 11.63 g of the target product (yield 74%, 3 steps).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：1.40(3H,t),2.70(3H,s),4.37(2H,q),5.20(2H,brs),7.21(1H,d),8.13(1H,d) 1 H-NMR data (400MHz, CDCl 3 /TMS δ (ppm)): 1.40 (3H, t), 2.70 (3H, s), 4.37 (2H, q), 5.20 (2H, brs), 7.21 (1H, d), 8.13 (1H, d)

(6)5-[5-胺基-3-(三氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸(本發明之化合物號碼：B-0001)的製造 (6) 5-[5-Amino-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methylbenzoic acid (of the present invention) Compound number: B-0001)

將氫氧化鋰一水合物2.71g(64.6mmol)添加至5-[5-胺基-3-(三氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸乙酯7.14g(21.5mmol)、甲醇40mL、四氫呋喃80mL及水40mL之混合物，於室溫下攪拌1.5小時。反應結束後，於減壓下濃縮所得到之反應混合物，將10%檸檬酸水溶液添加至殘渣以使反應混合物成為酸性而使固體析出。對固體進行過濾、水洗、乾燥而得到粗製目標物6.09g(產率93%)。 Lithium hydroxide monohydrate 2.71 g (64.6 mmol) was added to 5-[5-amino-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-4- A mixture of 7.14 g (21.5 mmol) of ethyl fluoro-2-methylbenzoate, 40 mL of methanol, 80 mL of tetrahydrofuran and 40 mL of water was stirred at room temperature for 1.5 hours. After the reaction was completed, the resulting reaction mixture was concentrated under reduced pressure, and a 10% citric acid aqueous solution was added to the residue to make the reaction mixture acidic, and a solid was precipitated. The solid was filtered, washed with water, and dried to obtain 6.09 g of a crude target substance (yield 93%).

1H-NMR資料(400MHz,DMSO-d6/TMS δ(ppm))：2.62(3H,s),7.04(2H,s),7.51(1H,d),7.98(1H,d),13.21(1H,brs) 1 H-NMR data (400MHz, DMSO-d 6 /TMS δ (ppm)): 2.62 (3H, s), 7.04 (2H, s), 7.51 (1H, d), 7.98 (1H, d), 13.21 ( 1H,brs)

(7)5-[5-胺基-3-(三氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基-N-(2,2,2-三氟乙基)苯甲醯胺的製造 (7) 5-[5-Amino-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methyl-N-(2, 2,2-Trifluoroethyl) Benzoamide

在冰冷下將2,2,2-三氟乙胺2.36g(23.8mmol)、三乙胺2.41g(23.8mmol)添加至5-[5-胺基-3-(三氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸3.62g(11.9mmol)、1-乙基-3-(3-二甲基胺基丙基)碳二亞胺鹽酸鹽2.74g(14.3mmol)、1-羥基苯并***一水合物2.19g(14.3mmol)、二氯甲烷80mL及四氫呋喃80mL之混合物，於室溫下攪拌24小時。反應結束後，於減壓下濃縮所得到之反應混合物，將乙酸乙酯添加至殘渣並藉由飽和碳酸氫鈉水溶液、飽和食鹽水洗淨有機層，並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=1：2)精製，而得到目標物4.05g(產率88%)。 Under ice cooling, 2.36 g (23.8 mmol) of 2,2,2-trifluoroethylamine and 2.41 g (23.8 mmol) of triethylamine were added to 5-[5-amino-3-(trifluoromethyl)-1H -1,2,4-triazol-1-yl]-4-fluoro-2-methylbenzoic acid 3.62g (11.9mmol), 1-ethyl-3-(3-dimethylaminopropyl) A mixture of 2.74 g (14.3 mmol) of carbodiimide hydrochloride, 2.19 g (14.3 mmol) of 1-hydroxybenzotriazole monohydrate, 80 mL of dichloromethane and 80 mL of tetrahydrofuran was stirred at room temperature for 24 hours. After the reaction was completed, the resulting reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, the organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 2) to obtain 4.05 g of the target product (yield 88%).

1H-NMR資料(400MHz,DMSO-d6/TMS δ(ppm))：2.43(3H,s),4.03-4.09(2H,M),7.04(2H,s),7.48(1H,d),7.60(1H,d),9.06(1H,t) 1 H-NMR data (400MHz, DMSO-d 6 /TMS δ (ppm)): 2.43 (3H, s), 4.03-4.09 (2H, M), 7.04 (2H, s), 7.48 (1H, d), 7.60(1H,d),9.06(1H,t)

[實施例2] [Example 2]

5-[5-乙醯胺-3-(三氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基-N-(2,2,2-三氟乙基)苯甲醯胺(本發明之化合物號碼：A-0077)的製造 5-[5-acetamide-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methyl-N-(2,2, 2-Trifluoroethyl) Benzoamide (Compound No. of the Invention: A-0077)

(1)5-[5-(N-乙醯基乙醯胺)-3-(三氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸乙酯(本發明之化合物號碼：C-0083)的製造 (1) 5-[5-(N-Acetylacetamide)-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-4-fluoro-2- Production of ethyl toluate (Compound No. of the present invention: C-0083)

將乙醯氯1.98g(25.2mmol)添加至5-[5-胺基-3-(三氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸乙酯0.84g(2.5mmol)的甲苯溶液20mL，加熱迴流4小時後，進一步添加乙醯氯20mL並加熱迴流20小時。於室溫下放置冷卻後，於減壓下濃縮所得到之反應混合物，藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=2：1)精製殘渣，而得到目標物1.02g(產率97%)。 1.98 g (25.2 mmol) of acetyl chloride was added to 5-[5-amino-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-4-fluoro-2 -20 mL of a toluene solution of 0.84 g (2.5 mmol) of ethyl toluate, heated to reflux for 4 hours, further added 20 mL of acetyl chloride and heated to reflux for 20 hours. After leaving to cool at room temperature, the resulting reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1) to obtain the target 1.02g (yield 97%).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：1.40(3H,t),2.34(6H,s),2.70(3H,s),4.36(2H,q),7.17(1H,d),8.09(1H,d) 1 H-NMR data (400MHz, CDCl 3 /TMS δ (ppm)): 1.40 (3H, t), 2.34 (6H, s), 2.70 (3H, s), 4.36 (2H, q), 7.17 (1H, d), 8.09 (1H, d)

(2)5-[5-乙醯胺-3-(三氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸乙酯(本發明之化合物號碼：C-0082)的製造 (2) 5-[5-acetamide-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methylbenzoic acid ethyl ester ( Production of the compound number of the present invention: C-0082)

將碳酸氫鈉0.62g(7.4mmol)添加至5-[5-(N-乙醯基乙醯胺)-3-(三氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸乙酯1.02g(2.45mmol)、乙醇5mL及水5mL之混合物，於室溫下攪拌3小時後，進一步添加碳酸鉀0.10g(0.72mmol)並於室溫下攪拌3小時。反應結束後添加乙酸乙酯，以 水、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=1：1)精製，而得到目標物0.78g(產率85%)。 Add 0.62 g (7.4 mmol) of sodium bicarbonate to 5-[5-(N-acetylacetamide)-3-(trifluoromethyl)-1H-1,2,4-triazole-1- Yl]-4-fluoro-2-methylbenzoic acid ethyl ester 1.02g (2.45mmol), a mixture of ethanol 5mL and water 5mL, stirred at room temperature for 3 hours, further added potassium carbonate 0.10g (0.72mmol) and Stir at room temperature for 3 hours. After the reaction, add ethyl acetate to The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1:1) to obtain 0.78 g of the target product (85% yield).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：1.39(3H,t),2.22(3H,brs),2.70(3H,s),4.37(2H,q),7.16(1H,d),8.15(1H,d) 1 H-NMR data (400MHz, CDCl 3 /TMS δ (ppm)): 1.39 (3H, t), 2.22 (3H, brs), 2.70 (3H, s), 4.37 (2H, q), 7.16 (1H, d), 8.15(1H,d)

(3)5-[5-乙醯胺-3-(三氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸(本發明之化合物號碼：B-0077)的製造 (3) 5-[5-acetamide-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methylbenzoic acid (present invention Compound number: B-0077)

將氫氧化鋰一水合物0.38g(9.1mmol)添加至5-[5-乙醯胺-3-(三氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸乙酯0.68g(1.8mmol)、甲醇10mL、四氫呋喃5mL及水10mL之混合物，於室溫下攪拌一小時。反應結束後添加乙酸乙酯，以2N鹽酸、水、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑而得到粗製目標物0.52g(產率83%)。 0.38 g (9.1 mmol) of lithium hydroxide monohydrate was added to 5-[5-acetamide-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-4 -A mixture of 0.68 g (1.8 mmol) of ethyl fluoro-2-methylbenzoate, 10 mL of methanol, 5 mL of tetrahydrofuran and 10 mL of water, and stirred at room temperature for one hour. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with 2N hydrochloric acid, water, and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 0.52 g of crude target product (yield 83%).

1H-NMR資料(400MHz,DMSO-d6/TMS δ(ppm))：1.98(3H,s),2.62(3H,s),7.52(1H,d),8.06(1H,d),11.20(1H,brs),13.23(1H,brs) 1 H-NMR data (400MHz, DMSO-d 6 /TMS δ (ppm)): 1.98 (3H, s), 2.62 (3H, s), 7.52 (1H, d), 8.06 (1H, d), 11.20 ( 1H,brs),13.23(1H,brs)

(4)5-[5-乙醯胺-3-(三氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基-N-(2,2,2-三氟乙基)苯甲醯胺的製造 (4) 5-[5-acetamide-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methyl-N-(2 ,2,2-trifluoroethyl)benzamide

在冰冷下將三乙胺0.28g(2.8mmol)添加至5-[5-乙醯胺-3-(三氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸0.40g(1.2mmol)、2,2,2-三氟乙胺0.14g(1.4mmol)、1-羥基苯并***一水合物0.16g(1.0mmol)、1-乙基-3-(3-二甲基胺基丙基)碳二亞胺鹽酸鹽0.27g(1.4mmol)及二氯甲烷10mL之混合物，於室溫下攪拌一晚。反應結束後添加乙酸乙酯，以水、飽和食鹽水 洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=1：2)精製，而得到目標物0.35g(產率71%)。 Under ice cooling, 0.28 g (2.8 mmol) of triethylamine was added to 5-[5-acetamide-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-4 -Fluoro-2-methylbenzoic acid 0.40g (1.2mmol), 2,2,2-trifluoroethylamine 0.14g (1.4mmol), 1-hydroxybenzotriazole monohydrate 0.16g (1.0mmol), A mixture of 0.27 g (1.4 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 10 mL of dichloromethane was stirred at room temperature overnight. After the reaction is completed, ethyl acetate is added, followed by water and saturated brine The organic layer was washed and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 2) to obtain 0.35 g of the target product (yield 71%).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：2.20(3H,brs),2.53(3H,s),4.04-4.15(2H,M),6.65(1H,t),7.15(1H,d),7.62(1H,d),8.89(1H,brs) 1 H-NMR data (400MHz, CDCl 3 /TMS δ (ppm)): 2.20 (3H, brs), 2.53 (3H, s), 4.04-4.15 (2H, M), 6.65 (1H, t), 7.15 ( 1H,d),7.62(1H,d),8.89(1H,brs)

[實施例3] [Example 3]

5-[5-胺基-3-(二氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基-N-(2,2,2-三氟乙基)苯甲醯胺(本發明之化合物號碼：A-0243)的製造 5-[5-Amino-3-(difluoromethyl)-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methyl-N-(2,2,2 -Production of trifluoroethyl) benzamide (compound number of the present invention: A-0243)

(1)5-[2-(2,2-二氟乙醯基)肼基]-4-氟-2-甲基苯甲酸乙酯的製造 (1) Production of ethyl 5-[2-(2,2-difluoroethylacyl)hydrazino]-4-fluoro-2-methylbenzoate

於50℃將4-氟-5-肼基-2-甲基苯甲酸乙酯3.37g(15.9mmol)、二氟乙酸乙酯11.8g(95.1mmol)及四氫呋喃30mL之混合物攪拌7.5小時後，進一步加熱迴流1.5小時。於室溫下放置冷卻後，於減壓下濃縮所得到之反應混合物，藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=3：1)精製殘渣而得到目標物2.50g(產率54%)。 A mixture of 3.37 g (15.9 mmol) of ethyl 4-fluoro-5-hydrazino-2-methylbenzoate, 11.8 g (95.1 mmol) of ethyl difluoroacetate and 30 mL of tetrahydrofuran was stirred at 50° C. for 7.5 hours, and further Heat to reflux for 1.5 hours. After leaving to cool at room temperature, the resulting reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 3: 1) to obtain the target substance. 2.50g (yield 54%).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：1.38(3H,t),2.52(3H,s),4.33(2H,q),6.06(1H,t),6.19(1H,s),6.94(1H,d),7.51(1H,d),8.08(1H,brs) 1 H-NMR data (400MHz, CDCl 3 /TMS δ (ppm)): 1.38 (3H, t), 2.52 (3H, s), 4.33 (2H, q), 6.06 (1H, t), 6.19 (1H, s), 6.94 (1H, d), 7.51 (1H, d), 8.08 (1H, brs)

(2)5-[2-(1-氯-2,2-二氟伸乙基)肼基]-4-氟-2-甲基苯甲酸乙酯的製造 (2) Production of ethyl 5-[2-(1-chloro-2,2-difluoroethylidene)hydrazino]-4-fluoro-2-methylbenzoate

將5-[2-(2,2-二氟乙醯基)肼基]-4-氟-2-甲基苯甲酸乙酯2.50g(8.61mmol)、四氯化碳3.97g(25.8mmol)、三苯基膦2.94g(11.2mmol)及乙腈30mL之混合物加熱迴流2小時。於室溫下放置冷卻後，於減壓下濃縮所得到之反應混合物，藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=4：1)精製殘渣而得到目標物2.38g(產率90%)。 Combine ethyl 5-[2-(2,2-difluoroethylacyl)hydrazino]-4-fluoro-2-methylbenzoate ethyl ester 2.50 g (8.61 mmol) and carbon tetrachloride 3.97 g (25.8 mmol) , A mixture of 2.94g (11.2mmol) of triphenylphosphine and 30mL of acetonitrile was heated to reflux for 2 hours. After leaving to cool at room temperature, the resulting reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 1) to obtain the target substance. 2.38g (yield 90%).

(3)5-[5-胺基-3-(二氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸乙酯(本發明之化合物號碼：C-0251)的製造 (3) 5-[5-Amino-3-(difluoromethyl)-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methylbenzoic acid ethyl ester (this Invention compound number: C-0251)

於室溫下將三乙胺2.34g(23.1mmol)添加至5-[2-(1-氯-2,2-二氟伸乙基)肼基]-4-氟-2-甲基苯甲酸乙酯2.38g(7.71mmol)、S-甲基異硫脲碘化氫鹽2.52g(11.6mmol)及四氫呋喃30mL之混合物，然後加熱迴流7.5小時。於室溫下放置冷卻後，於減壓下濃縮所得到之反應混合物，將水添加至殘渣並以乙酸乙酯進行萃取，以飽和食鹽水洗淨所得到有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=1：1至2：3)精製，而得到目標物0.76g(產率31%)。 2.34 g (23.1 mmol) of triethylamine was added to 5-[2-(1-chloro-2,2-difluoroethylidene)hydrazino]-4-fluoro-2-methylbenzoic acid at room temperature A mixture of 2.38 g (7.71 mmol) of ethyl ester, 2.52 g (11.6 mmol) of S-methylisothiourea hydrogen iodide salt and 30 mL of tetrahydrofuran was heated under reflux for 7.5 hours. After leaving to cool at room temperature, the resulting reaction mixture was concentrated under reduced pressure, water was added to the residue and extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate . The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1:1 to 2: 3) to obtain 0.76 g of the target product (yield 31%) ).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：1.40(3H,t),2.69(3H,s),4.37(2H,q),4.66(2H,brs),6.60(1H,t),7.19(1H,d),8.12(1H,d) 1 H-NMR data (400MHz, CDCl 3 /TMS δ (ppm)): 1.40 (3H, t), 2.69 (3H, s), 4.37 (2H, q), 4.66 (2H, brs), 6.60 (1H, t), 7.19(1H,d), 8.12(1H,d)

(4)5-[5-胺基-3-(二氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸(本發明之化合物號碼：B-0240)的製造 (4) 5-[5-Amino-3-(difluoromethyl)-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methylbenzoic acid (of the present invention) Compound number: B-0240)

將氫氧化鋰一水合物0.30g(7.2mmol)添加至5-[5-胺基-3-(二氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸乙酯0.76g(2.4mmol)、甲醇5mL、四氫呋喃10mL及水5mL之混合物，於0℃攪拌1.5小時後，進一步於室 溫下攪拌1小時。反應結束後，於減壓下濃縮所得到之反應混合物，將10%檸檬酸水溶液添加至殘渣，使反應混合物成為酸性而使固體析出。對固體進行過濾、水洗、乾燥而得到粗製目標物0.63g(產率91%)。 0.30 g (7.2 mmol) of lithium hydroxide monohydrate was added to 5-[5-amino-3-(difluoromethyl)-1H-1,2,4-triazol-1-yl]-4- A mixture of 0.76 g (2.4 mmol) of ethyl fluoro-2-methylbenzoate, 5 mL of methanol, 10 mL of tetrahydrofuran, and 5 mL of water was stirred at 0°C for 1.5 hours, and then further stored in a room Stir at room temperature for 1 hour. After the reaction was completed, the resulting reaction mixture was concentrated under reduced pressure, and a 10% citric acid aqueous solution was added to the residue to make the reaction mixture acidic and precipitate a solid. The solid was filtered, washed with water, and dried to obtain 0.63 g of crude target product (yield 91%).

1H-NMR資料(400MHz,DMSO-d6/TMS δ(ppm))：2.61(3H,s),6.81(2H,s),6.85(1H,t),7.49(1H,d),7.93(1H,d),13.22(1H,brs) 1 H-NMR data (400MHz, DMSO-d 6 /TMS δ (ppm)): 2.61 (3H, s), 6.81 (2H, s), 6.85 (1H, t), 7.49 (1H, d), 7.93 ( 1H,d),13.22(1H,brs)

(5)5-[5-胺基-3-(二氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基-N-(2,2,2-三氟乙基)苯甲醯胺的製造 (5) 5-[5-Amino-3-(difluoromethyl)-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methyl-N-(2, 2,2-Trifluoroethyl) Benzoamide

在冰冷下將2,2,2-三氟乙胺0.44g(4.4mmol)、三乙胺0.45g(4.5mmol)添加至5-[5-胺基-3-(二氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸0.63g(2.2mmol)、1-乙基-3-(3-二甲基胺基丙基)碳二亞胺鹽酸鹽0.51g(2.7mmol)、1-羥基苯并***一水合物0.40g(2.6mmol)、二氯甲烷20mL及四氫呋喃20mL之混合物，於室溫下攪拌24小時。反應結束後，於減壓下濃縮所得到之反應混合物，將乙酸乙酯添加至殘渣，以飽和碳酸氫鈉水溶液、飽和食鹽水來洗有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=1：2)精製，而得到目標物0.52g(產率64%)。 Under ice-cooling, add 2,4,2-trifluoroethylamine 0.44 g (4.4 mmol) and triethylamine 0.45 g (4.5 mmol) to 5-[5-amino-3-(difluoromethyl)-1H -1,2,4-triazol-1-yl]-4-fluoro-2-methylbenzoic acid 0.63g (2.2mmol), 1-ethyl-3-(3-dimethylaminopropyl) A mixture of 0.51 g (2.7 mmol) of carbodiimide hydrochloride, 0.40 g (2.6 mmol) of 1-hydroxybenzotriazole monohydrate, 20 mL of dichloromethane and 20 mL of tetrahydrofuran was stirred at room temperature for 24 hours. After the reaction was completed, the resulting reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 2) to obtain 0.52 g of the target product (64% yield).

1H-NMR資料(400MHz,DMSO-d6/TMS δ(ppm))：2.43(3H,s),4.05-4.09(2H,M),6.80(2H,s),6.85(1H,t),7.46(1H,d),7.54(1H,d),9.06(1H,t) 1 H-NMR data (400MHz, DMSO-d 6 /TMS δ (ppm)): 2.43 (3H, s), 4.05-4.09 (2H, M), 6.80 (2H, s), 6.85 (1H, t), 7.46(1H,d), 7.54(1H,d), 9.06(1H,t)

[實施例4] [Example 4]

4-氟-2-甲基-5-[5-甲基-3-(三氟甲基)-1H-1,2,4-***-1-基]-N-(2,2,2-三氟乙基)苯甲醯胺(本發明之化合物號碼：A-0102)的製造 4-fluoro-2-methyl-5-[5-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-N-(2,2,2 -Production of trifluoroethyl) benzamide (compound number of the present invention: A-0102)

(1)5-[2-(1-胺基-2,2,2-三氟伸乙基)肼基]-4-氟-2-甲基苯甲酸乙酯的製造 (1) Production of ethyl 5-[2-(1-amino-2,2,2-trifluoroethylidene)hydrazino]-4-fluoro-2-methylbenzoate

在冰冷下將28%氨水10mL添加至粗製之5-[2-(1-溴-2,2,2-三氟伸乙基)肼基]-4-氟-2-甲基苯甲酸乙酯2.58g(6.95mmol)的氯仿溶液30mL，於室溫下攪拌1小時。反應結束後添加氯仿，以水洗淨有機層並藉由無水硫酸鈉進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=4：1至3：1)精製，而得到目標物1.27g(產率60%)。 Under ice-cooling, add 10 mL of 28% ammonia water to the crude ethyl 5-[2-(1-bromo-2,2,2-trifluoroethylidene)hydrazino]-4-fluoro-2-methylbenzoate 30 mL of 2.58 g (6.95 mmol) of chloroform solution was stirred at room temperature for 1 hour. After the reaction was completed, chloroform was added, and the organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 1 to 3: 1) to obtain 1.27 g of the target substance (60% yield) ).

1H-NMR資料(300MHz,CDCl3/TMS δ(ppm))：1.38(3H,t),2.51(3H,s),4.33(2H,q),4.47(2H,brs),6.23(1H,s),6.89(1H,d),7.93(1H,d) 1 H-NMR data (300MHz, CDCl 3 /TMS δ (ppm)): 1.38 (3H, t), 2.51 (3H, s), 4.33 (2H, q), 4.47 (2H, brs), 6.23 (1H, s), 6.89 (1H, d), 7.93 (1H, d)

(2)4-氟-2-甲基-5-[5-甲基-3-(三氟甲基)-1H-1,2,4-***-1-基]苯甲酸乙酯(本發明之化合物號碼：C-0109)的製造 (2) 4-fluoro-2-methyl-5-[5-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]benzoic acid ethyl ester (this Invention compound number: C-0109)

在冰冷下將乙醯氯0.49g(6.2mmol)添加至5-[2-(1-胺基-2,2,2-三氟伸乙基)肼基]-4-氟-2-甲基苯甲酸乙酯1.27g(4.13mmol)的N,N-二甲基乙醯胺溶液10mL，於140℃攪拌1小時。於室溫下放置冷卻後添加乙酸乙酯，以水、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=4：1)精製，而得到目標物1.10g(產率80%)。 Under ice cooling, 0.49 g (6.2 mmol) of acetyl chloride was added to 5-[2-(1-amino-2,2,2-trifluoroethylidene)hydrazino]-4-fluoro-2-methyl A solution of 1.27 g (4.13 mmol) of ethyl benzoate in 10 mL of N,N-dimethylacetamide was stirred at 140° C. for 1 hour. After leaving to cool at room temperature, ethyl acetate was added, and the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4:1) to obtain 1.10 g of the target product (yield 80%).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：1.40(3H,t),2.47(3H,s),2.72(3H,s),4.38(2H,q),7.20(1H,d),8.09(1H,d) 1 H-NMR data (400 MHz, CDCl 3 /TMS δ (ppm)): 1.40 (3H, t), 2.47 (3H, s), 2.72 (3H, s), 4.38 (2H, q), 7.20 (1H, d), 8.09 (1H, d)

(3)4-氟-2-甲基-5-[5-甲基-3-(三氟甲基)-1H-1,2,4-***-1-基]苯甲酸(本發明之化合物號碼：B-0102)的製造 (3) 4-fluoro-2-methyl-5-[5-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]benzoic acid (of the present invention) Compound number: B-0102)

將濃鹽酸10mL添加至4-氟-2-甲基-5-[5-甲基-3-(三氟甲基)-1H-1,2,4-***-1-基]苯甲酸乙酯1.10g(3.32mmol)的乙酸溶液5mL，於100℃攪拌19小時。於室溫下放置冷卻後添加水，以氯仿進行萃取並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑而得到粗製目標物1.02g(產率定量性)。 10 mL of concentrated hydrochloric acid was added to ethyl 4-fluoro-2-methyl-5-[5-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]benzoate 5 mL of an acetic acid solution of 1.10 g (3.32 mmol) of the ester was stirred at 100° C. for 19 hours. After cooling at room temperature, water was added, extracted with chloroform, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.02 g of crude target substance (quantitative yield).

1H-NMR資料(300MHz,CDCl3/TMS δ(ppm))：2.48(3H,s),2.75(3H,s),7.24(1H,d),8.22(1H,d) 1 H-NMR data (300MHz, CDCl 3 /TMS δ (ppm)): 2.48 (3H, s), 2.75 (3H, s), 7.24 (1H, d), 8.22 (1H, d)

(4)4-氟-2-甲基-5-[5-甲基-3-(三氟甲基)-1H-1,2,4-***-1-基]-N-(2,2,2-三氟乙基)苯甲醯胺的製造 (4) 4-fluoro-2-methyl-5-[5-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-N-(2, 2,2-Trifluoroethyl) Benzoamide

在冰冷下將2,2,2-三氟乙胺0.33g(3.3mmol)、三乙胺0.33g(3.3mmol)添加至4-氟-2-甲基-5-[5-甲基-3-(三氟甲基)-1H-1,2,4-***-1-基]苯甲酸0.50g(1.7mmol)、1-乙基-3-(3-二甲基胺基丙基)碳二亞胺鹽酸鹽0.38g(2.0mmol)、1-羥基苯并***一水合物0.30g(2.0mmol)及二氯甲烷20mL之混合物，於室溫下攪拌18小時。反應結束後，於減壓下濃縮所得到之反應混合物，將乙酸乙酯添加至殘渣，以飽和碳酸氫鈉水溶液、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=2：1至1：1)精製，而得到目標物0.55g(產率87%)。 Under ice-cooling, add 2,3,2,2-trifluoroethylamine 0.33 g (3.3 mmol) and triethylamine 0.33 g (3.3 mmol) to 4-fluoro-2-methyl-5-[5-methyl-3 -(Trifluoromethyl)-1H-1,2,4-triazol-1-yl]benzoic acid 0.50g (1.7mmol), 1-ethyl-3-(3-dimethylaminopropyl) A mixture of 0.38 g (2.0 mmol) of carbodiimide hydrochloride, 0.30 g (2.0 mmol) of 1-hydroxybenzotriazole monohydrate and 20 mL of dichloromethane was stirred at room temperature for 18 hours. After the reaction was completed, the resulting reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, and the organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1 to 1:1) to obtain 0.55 g of the target substance (yield 87%) ).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：2.47(3H,s),2.56(3H,s),4.07-4.15(2H,M),6.11(1H,brs),7.24(1H,d),7.55(1H,d) 1 H-NMR data (400MHz, CDCl 3 /TMS δ (ppm)): 2.47 (3H, s), 2.56 (3H, s), 4.07-4.15 (2H, M), 6.11 (1H, brs), 7.24 ( 1H,d),7.55(1H,d)

[實施例5] [Example 5]

4-氟-2-甲基-5-[5-甲基-3-(三氟甲基)-1H-1,2,4-***-1-基]-N-[(甲基硫基)甲基]-N-(2,2,2-三氟乙基)苯甲醯胺(本發明之化合物號碼：A-0739)的製造 4-fluoro-2-methyl-5-[5-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-N-[(methylthio )Methyl]-N-(2,2,2-trifluoroethyl)benzamide (Compound No. of the present invention: A-0739)

於室溫下將氫化鈉0.20g(純度55%4.6mmol)添加至4-氟-2-甲基-5-[5-甲基-3-(三氟甲基)-1H-1,2,4-***-1-基]-N-(2,2,2-三氟乙基)苯甲醯胺0.50g(1.3mmol)的N,N-二甲基甲醯胺溶液20mL，於室溫下攪拌30分鐘。然後，於室溫下添加氯甲基甲基硫化物0.63g(6.5mmol)，並於室溫下進一步攪拌4小時。反應結束後添加水，以乙酸乙酯與己烷之混合溶劑進行萃取，以飽和食鹽水洗淨所得到之有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=4：1)精製，而得到目標物0.27g(產率47%)。 At room temperature, 0.20 g of sodium hydride (purity 55% 4.6 mmol) was added to 4-fluoro-2-methyl-5-[5-methyl-3-(trifluoromethyl)-1H-1,2, 4-Triazol-1-yl]-N-(2,2,2-trifluoroethyl)benzamide 0.50g (1.3mmol) in N,N-dimethylformamide 20mL, in the room Stir at room temperature for 30 minutes. Then, 0.63 g (6.5 mmol) of chloromethylmethyl sulfide was added at room temperature, and further stirred at room temperature for 4 hours. After the reaction was completed, water was added, extraction was performed with a mixed solvent of ethyl acetate and hexane, and the resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 1) to obtain 0.27 g of the target product (yield 47%).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：2.04(3H,S),2.41(3H,s),2.47(3H,s),4.43(4H,M),7.23(1H,d),7.36(1H,d) 1 H-NMR data (400MHz, CDCl 3 /TMS δ (ppm)): 2.04 (3H, S), 2.41 (3H, s), 2.47 (3H, s), 4.43 (4H, M), 7.23 (1H, d), 7.36 (1H, d)

[實施例6] [Example 6]

4-氟-2-甲基-5-[5-甲基-3-(三氟甲基)-1H-1,2,4-***-1-基]-N-(2,2,2-三氟乙基)硫代苯甲醯胺(本發明之化合物號碼：A-0727)的製造 4-fluoro-2-methyl-5-[5-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-N-(2,2,2 -Production of trifluoroethyl) thiobenzamide (the compound number of the present invention: A-0727)

將4-氟-2-甲基-5-[5-甲基-3-(三氟甲基)-1H-1,2,4-***-1-基]-N-(2,2,2-三氟乙基)苯甲醯胺0.80g(2.1mmol)、勞森試劑0.94g(2.3mmol)及甲苯30mL之混合物加熱迴流13.5小時。於室溫下放置冷卻後，藉由過濾去除所析出之固體並在減壓下濃縮濾液。藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=2：1)精製殘渣，而得到目標物0.14g(產率17%)。 4-fluoro-2-methyl-5-[5-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-N-(2,2, A mixture of 0.80 g (2.1 mmol) of 2-trifluoroethyl)benzamide, 0.94 g (2.3 mmol) of Lawesson's reagent and 30 mL of toluene was heated to reflux for 13.5 hours. After leaving to cool at room temperature, the precipitated solid was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2:1) to obtain 0.14 g of the target product (yield 17%).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：2.47(3H,s),2.49(3H,d),4.56-4.64(2H,M),7.19(1H,d),7.38(1H,brs),7.44(1H,d) 1 H-NMR data (400 MHz, CDCl 3 /TMS δ (ppm)): 2.47 (3H, s), 2.49 (3H, d), 4.56-4.64 (2H, M), 7.19 (1H, d), 7.38 ( 1H,brs),7.44(1H,d)

[實施例7] [Example 7]

5-[5-氯-3-(三氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基-N-(2,2,2-三氟乙基)苯甲醯胺(本發明之化合物號碼：A-0195)的製造 5-[5-chloro-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methyl-N-(2,2,2- Production of trifluoroethyl) benzamide (compound number of the present invention: A-0195)

在冰冷下將亞硝酸第三丁酯0.54g(5.2mmol)添加至5-[5-胺基-3-(三氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基-N-(2,2,2-三氟乙基)苯甲醯胺1.00g(2.60mmol)、氯化銅(II)0.70g(5.2mmol)及乙腈20mL之混合物，於室溫下攪拌4小時。反應結束後添加乙酸乙酯，以水、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=2：1)精製，而得到目標物0.86g(產率82%)。 Under ice cooling, 0.54 g (5.2 mmol) of tert-butyl nitrite was added to 5-[5-amino-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl] -4-fluoro-2-methyl-N-(2,2,2-trifluoroethyl)benzamide 1.00g (2.60mmol), copper(II) chloride 0.70g (5.2mmol) and acetonitrile 20mL The mixture was stirred at room temperature for 4 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1) to obtain 0.86 g of the target product (yield 82%).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：2.57(3H,s),4.09-4.13(2H,M),6.10(1H,s),7.25(1H,d),7.55(1H,d) 1 H-NMR data (400MHz, CDCl 3 /TMS δ (ppm)): 2.57 (3H, s), 4.09-4.13 (2H, M), 6.10 (1H, s), 7.25 (1H, d), 7.55 ( 1H,d)

[實施例8] [Example 8]

4-氟-5-[5-甲氧基-3-(三氟甲基)-1H-1,2,4-***-1-基]-2-甲基-N-(2,2,2-三氟乙基)苯甲醯胺(本發明之化合物號碼：A-0212)的製造 4-fluoro-5-[5-methoxy-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-2-methyl-N-(2,2, 2-Trifluoroethyl) Benzoamide (Compound No. of the Invention: A-0212)

將碳酸鉀0.23g(1.7mmol)添加至5-[5-氯-3-(三氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基-N-(2,2,2-三氟乙基)苯甲醯胺0.55g(1.4mmol)的甲醇溶液20mL，於室溫下攪拌4小時。反應結束後，於減壓下濃縮所得到之反 應混合物並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=2：1)精製殘渣，而得到目標物0.47g(產率86%)。 Add 0.23 g (1.7 mmol) of potassium carbonate to 5-[5-chloro-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methyl A solution of 0.55 g (1.4 mmol) of methyl-N-(2,2,2-trifluoroethyl)benzamide in 20 mL of methanol was stirred at room temperature for 4 hours. After the reaction is completed, the resulting reaction is concentrated under reduced pressure The mixture was purified and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1) to obtain 0.47 g of the target product (yield 86%).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：2.52(3H,s),4.06-4.14(2H,M),4.19(3H,s),6.09(1H,brs),7.17(1H,d),7.53(1H,d) 1 H-NMR data (400MHz, CDCl 3 /TMS δ (ppm)): 2.52 (3H, s), 4.06-4.14 (2H, M), 4.19 (3H, s), 6.09 (1H, brs), 7.17 ( 1H,d),7.53(1H,d)

[實施例9] [Example 9]

4-氟-2-甲基-N-(2,2,2-三氟乙基)-5-[3-(三氟甲基)-1H-1,2,4-***-1-基]苯甲醯胺(本發明之化合物號碼：A-0062)的製造 4-fluoro-2-methyl-N-(2,2,2-trifluoroethyl)-5-[3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl ] Production of benzamide (Compound No. of the present invention: A-0062)

將亞硝酸第三丁酯0.07g(0.68mmol)添加至5-[5-胺基-3-(三氟甲基)-1H-1,2,4-***-1-基]-4-氟-2-甲基-N-(2,2,2-三氟乙基)苯甲醯胺0.22g(0.57mmol)的四氫呋喃溶液15mL，並加熱迴流4小時。於室溫下放置冷卻後，於減壓下濃縮所得到之反應混合物並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=1：1)精製殘渣，而得到目標物0.16g(產率76%)。 0.07 g (0.68 mmol) of tert-butyl nitrite was added to 5-[5-amino-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-4- A solution of 0.22 g (0.57 mmol) of fluoro-2-methyl-N-(2,2,2-trifluoroethyl)benzamide in tetrahydrofuran was 15 mL, and heated to reflux for 4 hours. After leaving to cool at room temperature, the resulting reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1:1) to obtain the target 0.16g (yield 76%).

1H-NMR資料(400MHz,DMSO-d6/TMS δ(ppm))：2.43(3H,s),4.05-4.14(2H,M),7.59(1H,d),7.83(1H,d),9.18(1H,t),9.35(1H,s) 1 H-NMR data (400MHz, DMSO-d 6 /TMS δ (ppm)): 2.43 (3H, s), 4.05-4.14 (2H, M), 7.59 (1H, d), 7.83 (1H, d), 9.18(1H,t),9.35(1H,s)

[實施例10] [Example 10]

4-氟-5-[3-(1,1,2,3,3,3-六氟丙氧基)-5-甲基-1H-1,2,4-***-1-基]-2-甲基-N-(2,2,2-三氟乙基)苯甲醯胺(本發明之化合物號碼：A-1043)的製造 4-fluoro-5-[3-(1,1,2,3,3,3-hexafluoropropoxy)-5-methyl-1H-1,2,4-triazol-1-yl]- Production of 2-methyl-N-(2,2,2-trifluoroethyl)benzamide (Compound No. of the present invention: A-1043)

(1)1-(2-氟-4-甲基苯基)半卡肼的製造 (1) Production of 1-(2-fluoro-4-methylphenyl) hemicarbazide

將氰酸鉀7.72g(純度90%85.7mmol)添加至依據美國專利公報US2009/0156642號所記載的方法所製造之(2-氟-4-甲基苯基)肼6.00g (42.8mmol)的2M鹽酸溶液100mL，於室溫下攪拌3.5小時後，進一步添加氰酸鈉10.82g(純度90%149.8mmol)，於室溫下攪拌2.5小時。對所析出之固體進行過濾、水洗、乾燥而得到粗製目標物5.43g(產率69%)。 Potassium cyanate 7.72g (purity 90% 85.7mmol) was added to 6.00g of (2-fluoro-4-methylphenyl) hydrazine manufactured according to the method described in US Patent Publication No. US2009/0156642 100 mL of a 2M hydrochloric acid solution (42.8 mmol) was stirred at room temperature for 3.5 hours, then 10.82 g of sodium cyanate (purity 90% 149.8 mmol) was further added, and stirred at room temperature for 2.5 hours. The precipitated solid was filtered, washed with water, and dried to obtain 5.43 g of crude target product (yield 69%).

1H-NMR資料(300MHz,DMSO-d6/TMS δ(ppm))：2.15(3H,s),5.90(2H,brs),6.67(1H,t),6.78-6.86(2H,M),7.34(1H,brs),7.64(1H,brs) 1 H-NMR data (300MHz, DMSO-d 6 /TMS δ (ppm)): 2.15 (3H, s), 5.90 (2H, brs), 6.67 (1H, t), 6.78-6.86 (2H, M), 7.34(1H,brs),7.64(1H,brs)

(2)1-(2-氟-4-甲基苯基)-5-甲基-1H-1,2,4-***-3-醇(本發明之化合物號碼：D-2019)的製造 (2) Production of 1-(2-fluoro-4-methylphenyl)-5-methyl-1H-1,2,4-triazol-3-ol (the compound number of the present invention: D-2019)

於100℃將1-(2-氟-4-甲基苯基)半卡肼5.43g(29.6mmol)、對甲苯磺酸一水合物0.56g(2.9mmol)及原乙酸三乙酯(triethyl orthoacetate)50mL之混合物攪拌4.5小時。於室溫下放置冷卻後，於減壓下濃縮所得到之反應混合物，以二異丙醚洗淨所得到之粗生成物而得到目標物5.41g(產率88%)。 At 100 °C, 1-(2-fluoro-4-methylphenyl) hemicarbazide 5.43 g (29.6 mmol), p-toluenesulfonic acid monohydrate 0.56 g (2.9 mmol) and triethyl orthoacetate ) The 50 mL mixture was stirred for 4.5 hours. After leaving to cool at room temperature, the resulting reaction mixture was concentrated under reduced pressure, and the resulting crude product was washed with diisopropyl ether to obtain 5.41 g of the target product (yield 88%).

1H-NMR資料(300MHz,DMSO-d6/TMS δ(ppm))：2.13(3H,d),2.35(3H,s),7.14(1H,d),7.28(1H,dd),7.41(1H,t),11.03(1H,brs) 1 H-NMR data (300MHz, DMSO-d 6 /TMS δ (ppm)): 2.13 (3H, d), 2.35 (3H, s), 7.14 (1H, d), 7.28 (1H, dd), 7.41 ( 1H,t),11.03(1H,brs)

(3)1-(2-氟-4-甲基苯基)-3-(1,1,2,3,3,3-六氟丙氧基)-5-甲基-1H-1,2,4-***(本發明之化合物號碼：D-2023)的製造 (3) 1-(2-fluoro-4-methylphenyl)-3-(1,1,2,3,3,3-hexafluoropropoxy)-5-methyl-1H-1,2 ,4-Triazole (Compound No. of the present invention: D-2023)

在冰冷下將六氟丙烯8.50g(56.7mmol)吹入至1-(2-氟-4-甲基苯基)-5-甲基-1H-1,2,4-***-3-醇2.40g(11.6mmol)、三乙胺10mL及N,N-二甲基甲醯胺50mL之混合物，於室溫下攪拌16小時。反應結束後添加乙酸乙酯，以稀鹽酸、水、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=4：1)精製，而得到目標物2.21g(產率53%)。 Under ice-cooling, 8.50 g (56.7 mmol) of hexafluoropropylene was blown into 1-(2-fluoro-4-methylphenyl)-5-methyl-1H-1,2,4-triazol-3-ol A mixture of 2.40 g (11.6 mmol), 10 mL of triethylamine and 50 mL of N,N-dimethylformamide was stirred at room temperature for 16 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with dilute hydrochloric acid, water, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 1) to obtain 2.21 g of the target product (yield 53%).

1H-NMR資料(300MHz,CDCl3/TMS δ(ppm))：2.36(3H,d),2.43(3H,s),5.18-5.43(1H,M),7.06-7.10(2H,M),7.32(1H,t) 1 H-NMR data (300MHz, CDCl 3 /TMS δ (ppm)): 2.36 (3H, d), 2.43 (3H, s), 5.18-5.43 (1H, M), 7.06-7.10 (2H, M), 7.32(1H,t)

(4)1-(2-氟-5-碘-4-甲基苯基)-3-(1,1,2,3,3,3-六氟丙氧基)-5-甲基-1H-1,2,4-***(本發明之化合物號碼：D-1019)的製造 (4) 1-(2-fluoro-5-iodo-4-methylphenyl)-3-(1,1,2,3,3,3-hexafluoropropoxy)-5-methyl-1H -Manufacture of 1,1,2,4-triazole (Compound No. of the present invention: D-1019)

在冰冷下將N-碘琥珀醯亞胺1.40g(6.22mmol)添加至1-(2-氟-4-甲基苯基)-3-(1,1,2,3,3,3-六氟丙氧基)-5-甲基-1H-1,2,4-***2.12g(5.93mmol)的濃硫酸溶液15mL，於冰冷下攪拌5小時。反應結束後將反應溶液倒入於冰水，以乙酸乙酯進行萃取，以水、1N硫代硫酸鈉水溶液、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑而得到粗製目標物2.69g(產率94%)。 Under ice-cooling, 1.40 g (6.22 mmol) of N-iodosuccinimide was added to 1-(2-fluoro-4-methylphenyl)-3-(1,1,2,3,3,3-hexa Fluoropropoxy)-5-methyl-1H-1,2,4-triazole 2.12 g (5.93 mmol) of concentrated sulfuric acid solution 15 mL, and stirred under ice cooling for 5 hours. After the reaction, the reaction solution was poured into ice water, extracted with ethyl acetate, the organic layer was washed with water, 1N sodium thiosulfate aqueous solution, and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 2.69 g of a crude target product (yield 94%).

1H-NMR資料(300MHz,CDCl3/TMS δ(ppm))：2.38(3H,d),2.49(3H,s),5.17-5.41(1H,M),7.17(1H,d),7.88(1H,d) 1 H-NMR data (300MHz, CDCl 3 /TMS δ (ppm)): 2.38 (3H, d), 2.49 (3H, s), 5.17-5.41 (1H, M), 7.17 (1H, d), 7.88 ( 1H,d)

(5)4-氟-5-[3-(1,1,2,3,3,3-六氟丙氧基)-5-甲基-1H-1,2,4-***-1-基]-2-甲基苯甲腈(本發明之化合物號碼：D-0018)的製造 (5) 4-fluoro-5-(3-(1,1,2,3,3,3-hexafluoropropoxy)-5-methyl-1H-1,2,4-triazole-1- Yl]-2-methylbenzonitrile (Compound No. of the present invention: D-0018)

將氰化銅(I)1.25g(14.0mmol)添加至1-(2-氟-5-碘-4-甲基苯基)-3-(1,1,2,3,3,3-六氟丙氧基)-5-甲基-1H-1,2,4-***2.69g(5.57mmol)的N,N-二甲基乙醯胺溶液20mL，於100℃攪拌22.5小時。於室溫下放置冷卻後添加乙酸乙酯，以氨水、水、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=4：3)精製，而得到目標物1.94g(產率91%)。 Add 1.25g (14.0mmol) of copper(I) cyanide to 1-(2-fluoro-5-iodo-4-methylphenyl)-3-(1,1,2,3,3,3-hexa Fluoropropoxy)-5-methyl-1H-1,2,4-triazole 2.69 g (5.57 mmol) in N,N-dimethylacetamide solution 20 mL, and stirred at 100° C. for 22.5 hours. After leaving to cool at room temperature, ethyl acetate was added, and the organic layer was washed with ammonia water, water, and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 3) to obtain 1.94 g of the target product (yield 91%).

1H-NMR資料(300MHz,CDCl3/TMS δ(ppm))：2.39(3H,d),2.65(3H,s),5.16-5.40(1H,M),7.28(1H,d),7.77(1H,d) 1 H-NMR data (300MHz, CDCl 3 /TMS δ(ppm)): 2.39(3H,d), 2.65(3H,s),5.16-5.40(1H,M),7.28(1H,d),7.77( 1H,d)

(6)4-氟-5-[3-(1,1,2,3,3,3-六氟丙氧基)-5-甲基-1H-1,2,4-***-1-基]-2-甲基苯甲酸(本發明之化合物號碼：B-1035)的製造 (6) 4-fluoro-5-(3-(1,1,2,3,3,3-hexafluoropropoxy)-5-methyl-1H-1,2,4-triazole-1- -Yl]-2-methylbenzoic acid (the compound number of the present invention: B-1035)

於100℃將4-氟-5-[3-(1,1,2,3,3,3-六氟丙氧基)-5-甲基-1H-1,2,4-***-1-基]-2-甲基苯甲腈1.85g(4.84mmol)、1,4-二

Figure 108129126-A0202-12-0206-202
烷1mL及60%硫酸12mL之混合物攪拌20小時。於室溫下放置冷卻後添加乙酸乙酯，以水、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑而得到粗製目標物1.98g(產率定量性)。 4-fluoro-5-[3-(1,1,2,3,3,3-hexafluoropropoxy)-5-methyl-1H-1,2,4-triazole-1 at 100°C -Yl]-2-methylbenzonitrile 1.85g (4.84mmol), 1,4-di
Figure 108129126-A0202-12-0206-202
A mixture of 1 mL of alkane and 12 mL of 60% sulfuric acid was stirred for 20 hours. After leaving to cool at room temperature, ethyl acetate was added, and the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.98 g of crude target substance (quantitative yield).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：2.40(3H,d),2.73(3H,s),5.17-5.42(1H,M),7.21(1H,d),8.21(1H,d) 1 H-NMR data (400MHz, CDCl 3 /TMS δ (ppm)): 2.40 (3H, d), 2.73 (3H, s), 5.17-5.42 (1H, M), 7.21 (1H, d), 8.21 ( 1H,d)

(7)4-氟-5-[3-(1,1,2,3,3,3-六氟丙氧基)-5-甲基-1H-1,2,4-***-1-基]-2-甲基-N-(2,2,2-三氟乙基)苯甲醯胺的製造 (7) 4-fluoro-5-(3-(1,1,2,3,3,3-hexafluoropropoxy)-5-methyl-1H-1,2,4-triazole-1- Yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzamide

在冰冷下將2,2,2-三氟乙胺0.22g(2.2mmol)、N,N-二異丙基乙胺0.23g(1.8mmol)添加至4-氟-5-[3-(1,1,2,3,3,3-六氟丙氧基)-5-甲基-1H-1,2,4-***-1-基]-2-甲基苯甲酸0.60g(1.5mmol)、1-乙基-3-(3-二甲基胺基丙基)碳二亞胺鹽酸鹽0.35g(1.8mmol)、1-羥基苯并***一水合物0.28g(1.8mmol)及四氫呋喃20mL之混合物，於室溫下攪拌96小時。反應結束後，於減壓下濃縮所得到之反應混合物，將乙酸乙酯添加至殘渣，以飽和碳酸氫鈉水溶液、飽和食鹽水洗淨有機層，並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=1：1)精製，而得到目標物0.62g(產率86%)。 0.22 g (2.2 mmol) of 2,2,2-trifluoroethylamine and 0.23 g (1.8 mmol) of N,N-diisopropylethylamine were added to 4-fluoro-5-[3-(1 ,1,2,3,3,3-hexafluoropropoxy)-5-methyl-1H-1,2,4-triazol-1-yl]-2-methylbenzoic acid 0.60g (1.5mmol ), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride 0.35g (1.8mmol), 1-hydroxybenzotriazole monohydrate 0.28g (1.8mmol) A mixture of 20 mL of tetrahydrofuran was stirred at room temperature for 96 hours. After the reaction was completed, the resulting reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, and the organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1:1) to obtain 0.62 g of the target product (yield 86%).

1H-NMR資料(300MHz,CDCl3/TMS δ(ppm))：2.38(3H,d),2.52(3H,s),4.03-4.14(2H,M),5.16-5.40(1H,M),6.21(1H,t),7.19(1H,d),7.52(1H,d) 1 H-NMR data (300MHz, CDCl 3 /TMS δ(ppm)): 2.38(3H,d), 2.52(3H,s), 4.03-4.14(2H,M),5.16-5.40(1H,M), 6.21(1H,t), 7.19(1H,d), 7.52(1H,d)

[實施例11] [Example 11]

5-[5-胺基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***-1-基]-4-氟-2-甲基-N-(2,2,2-三氟乙基)苯甲醯胺(本發明之化合物號碼：A-2170)的製造 5-[5-Amino-3-(2,2,2-trifluoroethylthio)-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methyl- Production of N-(2,2,2-trifluoroethyl)benzamide (Compound No. of the present invention: A-2170)

(1)N-氰基二硫代亞胺基碳酸二(2,2,2-三氟乙基)的製造 (1) Manufacture of N-cyanodithioiminocarbonic acid bis(2,2,2-trifluoroethyl)

在冰冷下將三氟甲烷磺酸2,2,2-三氟乙酯20.06g(86.43mmol)添加至依據國際公開專利公報WO1994/026706號所記載的方法所製造之N-氰基二硫代亞胺基碳酸二鉀7.00g(36.0mmol)的二甲基亞碸溶液50mL，於室溫下攪拌67小時。反應結束後添加乙酸乙酯，以水、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑而得到粗製目標物6.81g(產率67%)。 Under ice cooling, 20.06 g (86.43 mmol) of 2,2,2-trifluoroethyl trifluoromethanesulfonate was added to N-cyanodithio produced by the method described in International Publication Patent Publication WO1994/026706 A solution of 7.00 g (36.0 mmol) of dipotassium imino carbonate in 50 mL of dimethyl sulfoxide was stirred at room temperature for 67 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 6.81 g of a crude target product (yield 67%).

1H-NMR資料(300MHz,CDCl3/TMS δ(ppm))：3.93(4H,q) 1 H-NMR data (300MHz, CDCl 3 /TMS δ(ppm)): 3.93(4H,q)

(2)5-[5-胺基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸乙酯(本發明之化合物號碼：C-2158)的製造 (2) 5-[5-Amino-3-(2,2,2-trifluoroethylthio)-1H-1,2,4-triazol-1-yl]-4-fluoro-2- Production of ethyl toluate (Compound No. of the present invention: C-2158)

將N-氰基二硫代亞胺基碳酸二(2,2,2-三氟乙基)6.81g(24.1mmol)添加至4-氟-5-肼基-2-甲基苯甲酸乙酯4.97g(23.4mmol)的乙醇溶液140mL，並加熱迴流5.5小時。於室溫下放置冷卻後，於減壓下濃縮所得到之反應混合物並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=1：1)精製殘渣，而得到目標物5.49g(產率62%)。 Add 6.81 g (24.1 mmol) of N-cyanodithioimidocarbonic acid bis(2,2,2-trifluoroethyl) to ethyl 4-fluoro-5-hydrazino-2-methylbenzoate 140 mL of 4.97 g (23.4 mmol) of ethanol solution was heated to reflux for 5.5 hours. After leaving to cool at room temperature, the resulting reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1:1) to obtain the target 5.49g (yield 62%).

1H-NMR資料(300MHz,CDCl3/TMS δ(ppm))：1.38(3H,t),2.66(3H,s),3.79(2H,q),4.35(2H,q),4.58(2H,brs),7.15(1H,d),8.09(1H,d) 1 H-NMR data (300MHz, CDCl 3 /TMS δ (ppm)): 1.38 (3H, t), 2.66 (3H, s), 3.79 (2H, q), 4.35 (2H, q), 4.58 (2H, brs), 7.15(1H,d), 8.09(1H,d)

(3)5-[5-胺基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸(本發明之化合物號碼：B-2143)的製造 (3) 5-[5-Amino-3-(2,2,2-trifluoroethylthio)-1H-1,2,4-triazol-1-yl]-4-fluoro-2- Production of toluic acid (Compound No. of the present invention: B-2143)

將氫氧化鋰一水合物1.83g(43.6mmol)添加至5-[5-胺基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸乙酯5.49g(14.5mmol)、乙醇15mL、四氫呋喃50mL及水25mL之混合物，於室溫下攪拌3小時。反應結束後添加乙酸乙酯，以2N鹽酸、水、飽和食鹽水洗淨有機層並藉由無水硫酸鈉進行乾燥。於減壓下餾除溶劑而得到粗製目標物5.56g(產率定量性)。 1.83g (43.6mmol) of lithium hydroxide monohydrate was added to 5-[5-amino-3-(2,2,2-trifluoroethylthio)-1H-1,2,4-triazole A mixture of 5.49 g (14.5 mmol) of ethyl-1-fluoro]-4-fluoro-2-methylbenzoate, 15 mL of ethanol, 50 mL of tetrahydrofuran and 25 mL of water was stirred at room temperature for 3 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with 2N hydrochloric acid, water, and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 5.56 g of crude target substance (quantitative yield).

1H-NMR資料(300MHz,DMSO-d6/TMS δ(ppm))：2.56(3H,s),4.00(2H,q),6.70(2H,brs),7.42(1H,d),7.84(1H,d) 1 H-NMR data (300MHz, DMSO-d 6 /TMS δ (ppm)): 2.56 (3H, s), 4.00 (2H, q), 6.70 (2H, brs), 7.42 (1H, d), 7.84 ( 1H,d)

(4)5-[5-胺基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***-1-基]-4-氟-2-甲基-N-(2,2,2-三氟乙基)苯甲醯胺的製造 (4) 5-[5-Amino-3-(2,2,2-trifluoroethylthio)-1H-1,2,4-triazol-1-yl]-4-fluoro-2- Production of methyl-N-(2,2,2-trifluoroethyl)benzamide

在冰冷下將1-乙基-3-(3-二甲基胺基丙基)碳二亞胺鹽酸鹽3.28g(17.1mmol)添加至5-[5-胺基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸3.00g(8.56mmol)、三氟乙胺3.39g(34.2mmol)、1-羥基苯并***一水合物2.62g(17.1mmol)、N,N-二異丙基乙胺2.21g(17.1mmol)及四氫呋喃60mL之混合物，於室溫下攪拌63小時。反應結束後，於減壓下濃縮所得到之反應混合物，將乙酸乙酯添加至殘渣，以飽和碳酸氫鈉水溶液、飽和食鹽水洗淨有機層並藉由無水硫酸鈉進行乾燥。於 減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，氯仿：甲醇=10：1至5：1)精製，而得到目標物2.89g(產率78%)。 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride 3.28g (17.1mmol) was added to 5-[5-amino-3-(2, 2,2-trifluoroethylthio)-1H-1,2,4-triazol-1-yl)-4-fluoro-2-methylbenzoic acid 3.00g (8.56mmol), trifluoroethylamine 3.39 A mixture of g (34.2 mmol), 1-hydroxybenzotriazole monohydrate 2.62 g (17.1 mmol), N,N-diisopropylethylamine 2.21 g (17.1 mmol) and tetrahydrofuran 60 mL, stirred at room temperature 63 hours. After the reaction was completed, the resulting reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, and the organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine and dried over anhydrous sodium sulfate. in The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, chloroform: methanol = 10:1 to 5:1) to obtain 2.89 g of the target substance (yield 78%).

1H-NMR資料(300MHz,DMSO-d6/TMS δ(ppm))：2.37(3H,s),3.95-4.09(4H,M),6.70(2H,brs),7.38(1H,d),7.45(1H,d),9.01(1H,t) 1 H-NMR data (300MHz, DMSO-d 6 /TMS δ (ppm)): 2.37 (3H, s), 3.95-4.09 (4H, M), 6.70 (2H, brs), 7.38 (1H, d), 7.45(1H,d),9.01(1H,t)

[實施例12] [Example 12]

5-[3-(二氟甲基硫基)-5-甲基-1H-1,2,4-***-1-基]-4-氟-2-甲基-N-(2,2,2-三氟乙基)苯甲醯胺(本發明之化合物號碼：A-2114)的製造 5-[3-(Difluoromethylthio)-5-methyl-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methyl-N-(2,2 ,2-Trifluoroethyl) Benzoamide (Compound No. of the Invention: A-2114)

(1)5-(3-胺基-5-甲基-1H-1,2,4-***-1-基)-4-氟-2-甲基苯甲酸乙酯(本發明之化合物號碼：C-2319)的製造 (1) 5-(3-Amino-5-methyl-1H-1,2,4-triazol-1-yl)-4-fluoro-2-methylbenzoic acid ethyl ester (Compound No. of the present invention) : C-2319)

在冰冷下將三乙胺9.54g(94.3mmol)、乙醯氯2.96g(37.7mmol)添加至S-甲基異硫脲氫碘酸鹽8.22g(37.7mmol)的四氫呋喃溶液50mL，於室溫下攪拌30分鐘。在冰冷下將4-氟-5-肼基-2-甲基苯甲酸乙酯4.00g(18.9mmol)的四氫呋喃溶液20mL滴入於所得到之反應混合物，並加熱迴流2小時。放置冷卻至室溫後添加乙酸乙酯，以水、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑，添加乙醇40mL、濃硫酸1mL並加熱迴流一晚。於室溫下放置冷卻後，添加飽和碳酸氫鈉溶液、乙酸乙酯，以水、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑，以乙酸乙酯、正已烷洗淨所析出之結晶而得到目標物2.74g(產率52%)。 Under ice cooling, 9.54 g (94.3 mmol) of triethylamine and 2.96 g (37.7 mmol) of acetyl chloride were added to a solution of 8.22 g (37.7 mmol) of S-methylisothiourea hydroiodide in 50 mL of tetrahydrofuran at room temperature Stir for 30 minutes. Under ice cooling, 20 mL of a tetrahydrofuran solution of 4.00 g (18.9 mmol) of ethyl 4-fluoro-5-hydrazino-2-methylbenzoate was dropped into the resulting reaction mixture, and heated to reflux for 2 hours. After leaving to cool to room temperature, ethyl acetate was added, and the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, 40 mL of ethanol and 1 mL of concentrated sulfuric acid were added and heated to reflux overnight. After leaving to cool at room temperature, a saturated sodium bicarbonate solution and ethyl acetate were added, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the precipitated crystals were washed with ethyl acetate and n-hexane to obtain 2.74 g of the target product (yield 52%).

1H-NMR資料(400MHz,CDCl3/TMSδ(ppm))：1.38(3H,t),2.29(3H,d),2.67(3H,s),4.20(2H,brs),4.35(2H,q),7.13(1H,d),8.06(1H,d) 1 H-NMR data (400MHz, CDCl 3 / TMSδ (ppm)): 1.38 (3H, t), 2.29 (3H, d), 2.67 (3H, s), 4.20 (2H, brs), 4.35 (2H, q ), 7.13(1H,d), 8.06(1H,d)

(2)4-氟-2-甲基-5-[5-甲基-3-(甲基硫基)-1H-1,2,4-***-1-基]苯甲酸乙酯(本發明之化合物號碼：C-2009)的製造 (2) 4-fluoro-2-methyl-5-[5-methyl-3-(methylthio)-1H-1,2,4-triazol-1-yl]benzoic acid ethyl ester (this Invention compound number: C-2009)

在冰冷下將亞硝酸第三丁酯17.38g(168.5mmol)添加至5-(3-胺基-5-甲基-1H-1,2,4-***-1-基)-4-氟-2-甲基苯甲酸乙酯21.11g(75.86mmol)、二硫化二甲基14.29g(151.7mmol)、氯仿150mL之混合物，於室溫下攪拌24小時。於減壓下濃縮所得到之反應混合物，並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=4：3)精製殘渣而得到目標物14.96g(產率64%)。 Under ice cooling, 17.38 g (168.5 mmol) of tert-butyl nitrite was added to 5-(3-amino-5-methyl-1H-1,2,4-triazol-1-yl)-4-fluoro A mixture of 21.11 g (75.86 mmol) of ethyl-2-methylbenzoate, 14.29 g (151.7 mmol) of dimethyl disulfide, and 150 mL of chloroform was stirred at room temperature for 24 hours. The resulting reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 3) to obtain 14.96 g of the target product (yield 64%) ).

1H-NMR資料(300MHz,CDCl3/TMS δ(ppm))：1.37(3H,t),2.35(3H,d),2.60(3H,s),2.67(3H,s),4.34(2H,q),7.14(1H,d),8.06(1H,d) 1 H-NMR data (300MHz, CDCl 3 /TMS δ (ppm)): 1.37 (3H, t), 2.35 (3H, d), 2.60 (3H, s), 2.67 (3H, s), 4.34 (2H, q), 7.14(1H,d), 8.06(1H,d)

(3)4-氟-2-甲基-5-[5-甲基-3-(甲基亞磺醯基)-1H-1,2,4-***-1-基]苯甲酸乙酯(本發明之化合物號碼：C-2011)的製造 (3) 4-fluoro-2-methyl-5-[5-methyl-3-(methylsulfinyl)-1H-1,2,4-triazol-1-yl]benzoic acid ethyl ester (Compound No. of the present invention: C-2011)

在冰冷下將間氯過苯甲酸13.24g(純度：約65%、49.02mmol)添加至4-氟-2-甲基-5-[5-甲基-3-(甲基硫基)-1H-1,2,4-***-1-基]苯甲酸乙酯15.90g(51.40mmol)的二氯甲烷溶液120mL，並攪拌2小時。反應結束後，將1N硫代硫酸鈉水溶液添加至反應溶液中以使過剩的過氧化物分解。然後，添加乙酸乙酯，以飽和碳酸氫鈉水溶液、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=1：4至1：10)精製，而得到目標物13.43g(產率80%)。 Under ice cooling, 13.24 g of m-chloroperbenzoic acid (purity: about 65%, 49.02 mmol) was added to 4-fluoro-2-methyl-5-[5-methyl-3-(methylthio)-1H -120 mL of a dichloromethane solution of 15.90 g (51.40 mmol) of ethyl -1,2,4-triazol-1-yl]benzoate and stirred for 2 hours. After the reaction was completed, a 1N sodium thiosulfate aqueous solution was added to the reaction solution to decompose excess peroxide. Then, ethyl acetate was added, and the organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 4 to 1: 10) to obtain 13.43 g of the target product (80% yield) ).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：1.37(3H,t),2.45(3H,d),2.67(3H,s),3.05(3H,s),4.34(2H,q),7.18(1H,d),8.11(1H,d) 1 H-NMR data (400MHz, CDCl 3 /TMS δ (ppm)): 1.37 (3H, t), 2.45 (3H, d), 2.67 (3H, s), 3.05 (3H, s), 4.34 (2H, q), 7.18(1H,d),8.11(1H,d)

(4)4-氟-5-(3-巰基-5-甲基-1H-1,2,4-***-1-基)-2-甲基苯甲酸甲酯(本發明之化合物號碼：C-2002)的製造 (4) 4-fluoro-5-(3-mercapto-5-methyl-1H-1,2,4-triazol-1-yl)-2-methylbenzoic acid methyl ester (the compound number of the present invention: C-2002)

將三氟乙酸酐52.02g(247.7mmol)添加至4-氟-2-甲基-5-[5-甲基-3-(甲基亞磺醯基)-1H-1,2,4-***-1-基]苯甲酸乙酯13.43g(41.28mmol)的氯仿溶液150mL，於室溫下攪拌14小時。於減壓下餾除溶劑並將殘渣溶解於甲醇100mL。在冰冷下添加碳酸鉀17.12g(123.9mmol)，於室溫下攪拌5.5小時。添加鹽酸調整成pH5後，添加飽和食鹽水並以乙酸乙酯進行萃取，並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑而得到粗製目標物。不進行精製而直接使用在下一步驟。 52.02g (247.7mmol) of trifluoroacetic anhydride was added to 4-fluoro-2-methyl-5-[5-methyl-3-(methylsulfinyl)-1H-1,2,4-tri 150 mL of a chloroform solution of 13.43 g (41.28 mmol) of ethyl oxazol-1-yl]benzoate was stirred at room temperature for 14 hours. The solvent was distilled off under reduced pressure and the residue was dissolved in 100 mL of methanol. Under ice cooling, 17.12 g (123.9 mmol) of potassium carbonate was added, and the mixture was stirred at room temperature for 5.5 hours. After adding hydrochloric acid to adjust to pH 5, saturated brine was added, extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a crude target. It is used directly in the next step without purification.

1H-NMR資料(300MHz,CDCl3/TMS δ(ppm))：2.44(3H,d),2.70(3H,s),3.90(3H,s),7.19(1H,d),8.08(1H,d) 1 H-NMR data (300MHz, CDCl 3 /TMS δ (ppm)): 2.44 (3H, d), 2.70 (3H, s), 3.90 (3H, s), 7.19 (1H, d), 8.08 (1H, d)

(5)5-[3-(二氟甲基硫基)-5-甲基-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸甲基(本發明之化合物號碼：C-2111)的製造 (5) 5-[3-(difluoromethylthio)-5-methyl-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methylbenzoic acid methyl (Compound No. of the present invention: C-2111)

將氯二氟甲烷吹入至粗製的4-氟-5-(3-巰基-5-甲基-1H-1,2,4-***-1-基)-2-甲基苯甲酸甲酯1.20g(純度：約63%、2.69mmol)、碳酸鉀0.56g(4.1mmol)、Rongalite0.21g(1.4mmol)及N,N-二甲基甲醯胺10mL之混合物，於60℃攪拌5小時。反應結束後添加乙酸乙酯，以水、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝 膠管柱層析(展開溶劑，正己烷：乙酸乙酯=3：2)精製，而得到目標物0.42g(產率47%)。 Chlorodifluoromethane is blown into the crude methyl 4-fluoro-5-(3-mercapto-5-methyl-1H-1,2,4-triazol-1-yl)-2-methylbenzoate A mixture of 1.20g (purity: about 63%, 2.69mmol), potassium carbonate 0.56g (4.1mmol), Rongalite 0.21g (1.4mmol) and N,N-dimethylformamide 10mL, stirred at 60°C for 5 hours . After the reaction was completed, ethyl acetate was added, and the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. Distill off the solvent under reduced pressure and condense by silica Column chromatography (developing solvent, n-hexane: ethyl acetate = 3: 2) was purified to obtain 0.42 g of the target product (yield 47%).

1H-NMR資料(300MHz,CDCl3/TMS δ(ppm))：2.40(3H,d),2.69(3H,s),3.89(3H,s),7.14(1H,d),7.46(1H,t),8.07(1H,d) 1 H-NMR data (300 MHz, CDCl 3 /TMS δ (ppm)): 2.40 (3H, d), 2.69 (3H, s), 3.89 (3H, s), 7.14 (1H, d), 7.46 (1H, t),8.07(1H,d)

(6)5-[3-(二氟甲基硫基)-5-甲基-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸(本發明之化合物號碼：B-2098)的製造 (6) 5-[3-(difluoromethylthio)-5-methyl-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methylbenzoic acid (this Invention compound number: B-2098)

將氫氧化鋰一水合物0.16g(3.8mmol)添加至5-[3-(二氟甲基硫基)-5-甲基-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸甲酯0.42g(1.3mmol)、乙醇5mL、四氫呋喃10mL及水5mL之混合物，於室溫下攪拌1小時。反應結束後，於減壓下濃縮所得到之反應混合物，將乙酸乙酯添加至殘渣，藉由稀檸檬酸水溶液、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑而得到粗製目標物0.45g(產率定量性)。 0.16g (3.8mmol) of lithium hydroxide monohydrate was added to 5-[3-(difluoromethylthio)-5-methyl-1H-1,2,4-triazol-1-yl]- A mixture of 0.42 g (1.3 mmol) of methyl 4-fluoro-2-methylbenzoate, 5 mL of ethanol, 10 mL of tetrahydrofuran and 5 mL of water was stirred at room temperature for 1 hour. After the reaction was completed, the resulting reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, the organic layer was washed with dilute citric acid aqueous solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 0.45 g of crude target product (quantitative yield).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：2.43(3H,d),2.75(3H,s),7.23(1H,d),7.47(1H,t),8.21(1H,d) 1 H-NMR data (400MHz, CDCl 3 /TMS δ (ppm)): 2.43 (3H, d), 2.75 (3H, s), 7.23 (1H, d), 7.47 (1H, t), 8.21 (1H, d)

(7)5-[3-(二氟甲基硫基)-5-甲基-1H-1,2,4-***-1-基]-4-氟-2-甲基-N-(2,2,2-三氟乙基)苯甲醯胺的製造 (7) 5-[3-(difluoromethylthio)-5-methyl-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methyl-N-( 2,2,2-Trifluoroethyl) Benzoamide

在冰冷下將2,2,2-三氟乙胺0.10g(1.0mmol)、N,N-二異丙基乙胺0.10g(0.99mmol)添加至5-[3-(二氟甲基硫基)-5-甲基-1H-1,2,4-***-1-基]-4-氟-2-甲基苯甲酸0.21g(0.66mmol)、1-乙基-3-(3-二甲基胺基丙基)碳二亞胺鹽酸鹽0.15g(0.78mmol)、1-羥基苯并***一水合物0.12g(0.78mmol)及四氫呋喃15mL之混合物，於室溫下攪拌18小時。反應結束後，於減壓下濃縮所得到之反應混合物，將乙酸乙酯添加至殘渣，以飽和 碳酸氫鈉水溶液、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=1：2)精製，而得到目標物0.21g(產率80%)。 Under ice-cooling, add 0.10 g (1.0 mmol) of 2,2,2-trifluoroethylamine and 0.10 g (0.99 mmol) of N,N-diisopropylethylamine to 5-[3-(difluoromethylsulfide Yl)-5-methyl-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methylbenzoic acid 0.21g (0.66mmol), 1-ethyl-3-(3 -A mixture of 0.15g (0.78mmol) of dimethylaminopropyl) carbodiimide hydrochloride, 0.12g (0.78mmol) of 1-hydroxybenzotriazole monohydrate and 15mL of tetrahydrofuran, stirred at room temperature 18 hours. After the reaction was completed, the resulting reaction mixture was concentrated under reduced pressure, and ethyl acetate was added to the residue to saturate The organic layer was washed with an aqueous solution of sodium bicarbonate and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 2) to obtain 0.21 g of the target product (yield 80%).

1H-NMR資料(300MHz,CDCl3/TMS δ(ppm))：2.40(3H,d),2.53(3H,s),4.03-4.14(2H,M),6.18(1H,t),7.19(1H,d),7.43(1H,t),7.52(1H,d) 1 H-NMR data (300 MHz, CDCl 3 /TMS δ (ppm)): 2.40 (3H, d), 2.53 (3H, s), 4.03-4.14 (2H, M), 6.18 (1H, t), 7.19 ( 1H,d),7.43(1H,t),7.52(1H,d)

[實施例13] [Example 13]

5-[3-氯-5-甲基-1H-1,2,4-***-1-基]-4-氟-2-甲基-N-(2,2,2-三氟乙基)苯甲醯胺(本發明之化合物號碼：A-2453)的製造 5-[3-chloro-5-methyl-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methyl-N-(2,2,2-trifluoroethyl ) Production of benzamide (Compound No. of the present invention: A-2453)

(1)5-(3-氯-5-甲基-1H-1,2,4-***-1-基)-4-氟-2-甲基苯甲酸乙酯(本發明之化合物號碼：C-2342)的製造 (1) 5-(3-chloro-5-methyl-1H-1,2,4-triazol-1-yl)-4-fluoro-2-methylbenzoic acid ethyl ester (Compound No. of the present invention: C-2342)

在冰冷下將亞硝酸第三丁酯0.82g(7.2mmol)的乙腈溶液5mL添加至5-(3-胺基-5-甲基-1H-1,2,4-***-1-基)-4-氟-2-甲基苯甲酸乙酯1.00g(3.59mmol)、氯化銅(II)0.97g(7.2mmol)、乙腈10mL之混合物，並攪拌2小時。反應結束後添加乙酸乙酯，以水、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=2：1)精製，而得到目標物0.58g(產率54%)。 Under ice-cooling, 5 mL of an acetonitrile solution of 0.82 g (7.2 mmol) of tert-butyl nitrite was added to 5-(3-amino-5-methyl-1H-1,2,4-triazol-1-yl) A mixture of 1.00 g (3.59 mmol) of ethyl-4-fluoro-2-methylbenzoate, 0.97 g (7.2 mmol) of copper(II) chloride and 10 mL of acetonitrile, and stirred for 2 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1) to obtain 0.58 g of the target product (yield 54%).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：1.39(3H,t),2.40(3H,d),2.70(3H,s),4.37(2H,q),7.18(1H,d),8.08(1H,d) 1 H-NMR data (400 MHz, CDCl 3 /TMS δ (ppm)): 1.39 (3H, t), 2.40 (3H, d), 2.70 (3H, s), 4.37 (2H, q), 7.18 (1H, d), 8.08 (1H, d)

(2)5-(3-氯-5-甲基-1H-1,2,4-***-1-基)-4-氟-2-甲基苯甲酸(本發明之化合物號碼：B-2320)的製造 (2) 5-(3-chloro-5-methyl-1H-1,2,4-triazol-1-yl)-4-fluoro-2-methylbenzoic acid (the compound number of the present invention: B- 2320) Manufacturing

將氫氧化鋰一水合物0.31g(7.4mmol)添加至5-(3-氯-5-甲基-1H-1,2,4-***-1-基)-4-氟-2-甲基苯甲酸乙酯0.44g(1.5mmol)、甲醇10mL、四氫呋喃10mL及水10mL之混合物，於室溫下攪拌一晚。反應結束後添加乙酸乙酯，以2N鹽酸、水、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並以二異丙醚洗淨所析出之結晶，而得到目標物0.25g(產率63%)。 Add 0.31 g (7.4 mmol) of lithium hydroxide monohydrate to 5-(3-chloro-5-methyl-1H-1,2,4-triazol-1-yl)-4-fluoro-2-methyl A mixture of 0.44 g (1.5 mmol) of ethyl benzoate, 10 mL of methanol, 10 mL of tetrahydrofuran and 10 mL of water was stirred at room temperature overnight. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with 2N hydrochloric acid, water, and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the precipitated crystals were washed with diisopropyl ether to obtain 0.25 g of the target substance (yield 63%).

1H-NMR資料(400MHz,DMSO-d6/TMS δ(ppm))：2.34(3H,s),2.63(3H,s),7.57(1H,d),8.10(1H,d),13.31(1H,brs) 1 H-NMR data (400MHz, DMSO-d 6 /TMS δ (ppm)): 2.34 (3H, s), 2.63 (3H, s), 7.57 (1H, d), 8.10 (1H, d), 13.31 ( 1H,brs)

(3)5-[3-氯-5-甲基-1H-1,2,4-***-1-基]-4-氟-2-甲基-N-(2,2,2-三氟乙基)苯甲醯胺的製造 (3) 5-[3-chloro-5-methyl-1H-1,2,4-triazol-1-yl]-4-fluoro-2-methyl-N-(2,2,2-tri Fluoroethyl) benzamide

將2,2,2-三氟乙胺0.11g(1.1mmol)、1-羥基苯并***一水合物0.13g(0.85mmol)、1-乙基-3-(3-二甲基胺基丙基)碳二亞胺鹽酸鹽0.21g(1.1mmol)添加至5-(3-氯-5-甲基-1H-1,2,4-***-1-基)-4-氟-2-甲基苯甲酸0.25g(0.93mmol)的二氯甲烷溶液10mL。在冰冷下添加三乙胺0.23g(2.3mmol)並於室溫下攪拌一晚。反應結束後添加乙酸乙酯，以水、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並以正己烷洗淨所析出之結晶，而得到目標物0.25g(產率77%)。 0.12g (1.1mmol) of 2,2,2-trifluoroethylamine, 0.13g (0.85mmol) of 1-hydroxybenzotriazole monohydrate, 1-ethyl-3-(3-dimethylamino Propyl)carbodiimide hydrochloride 0.21g (1.1mmol) was added to 5-(3-chloro-5-methyl-1H-1,2,4-triazol-1-yl)-4-fluoro- A solution of 2-methylbenzoic acid 0.25g (0.93mmol) in dichloromethane 10mL. 0.23 g (2.3 mmol) of triethylamine was added under ice cooling and stirred at room temperature overnight. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the precipitated crystals were washed with n-hexane to obtain 0.25 g of the target product (yield 77%).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：2.39(3H,d),2.54(3H,s),4.04-4.14(2H,M),6.52(1H,t),7.19(1H,d),7.54(1H,d) 1 H-NMR data (400MHz, CDCl 3 /TMS δ (ppm)): 2.39 (3H, d), 2.54 (3H, s), 4.04-4.14 (2H, M), 6.52 (1H, t), 7.19 ( 1H,d),7.54(1H,d)

[實施例14] [Example 14]

4-氟-2-甲基-5-[5-甲基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***-1-基]-N-(2,2,2-三氟乙基)苯甲醯胺(本發明之化合物號碼：A-2261)的製造 4-fluoro-2-methyl-5-[5-methyl-3-(2,2,2-trifluoroethylthio)-1H-1,2,4-triazol-1-yl]- Production of N-(2,2,2-trifluoroethyl)benzamide (Compound No. of the present invention: A-2261)

(1)5-甲基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***的製造 (1) Production of 5-methyl-3-(2,2,2-trifluoroethylthio)-1H-1,2,4-triazole

將1,1,1-三氟-2-碘乙烷14.59g(69.50mmol)添加至依據Indian J.Chem.Sec.B,38B卷，18頁至23頁(1999年)所記載的方法所製造之5-甲基-1,2-二氫-3H-1,2,4-***-3-硫酮4.00g(34.7mmol)、碳酸鉀5.76g(41.7mmol)、Rongalite1.61g(10.5mmol)及N,N-二甲基甲醯胺20mL之混合物，並於40℃攪拌3日。反應結束後添加乙酸乙酯，以稀碳酸氫鈉水溶液、飽和食鹽水洗淨有機層並藉由無水硫酸鈉進行乾燥。於減壓下餾除溶劑而得到粗製目標物6.04g(產率88%)。 Add 1,59-trifluoro-2-iodoethane 14.59g (69.50mmol) to the method described in Indian J. Chem. Sec. B, Volume 38B, pages 18 to 23 (1999) Production of 5-methyl-1,2-dihydro-3H-1,2,4-triazole-3-thione 4.00g (34.7mmol), potassium carbonate 5.76g (41.7mmol), Rongalite 1.61g (10.5 mmol) and 20 mL of N,N-dimethylformamide, and stirred at 40°C for 3 days. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with dilute aqueous sodium bicarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 6.04 g of crude target product (yield 88%).

1H-NMR資料(400MHz,DMSO-d6/TMS δ(ppm))：2.33(3H,s),4.07(2H,q),13.77(1H,brs) 1 H-NMR data (400MHz, DMSO-d 6 /TMS δ (ppm)): 2.33 (3H, s), 4.07 (2H, q), 13.77 (1H, brs)

(2)3-氟-4-[5-甲基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***-1-基]苯甲醛(本發明之化合物號碼：D-2032)的製造 (2) 3-fluoro-4-[5-methyl-3-(2,2,2-trifluoroethylthio)-1H-1,2,4-triazol-1-yl]benzaldehyde ( The compound number of the present invention: D-2032)

將5-甲基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***3.00g(15.2mmol)、3,4-二氟苯甲醛3.24g(22.8mmol)、碳酸鉀3.15g(22.8mmol)及乙腈18mL之混合物加熱迴流2.5小時。於室溫下放置冷卻後，添加乙酸乙酯與正己烷並以矽藻土過濾不溶物。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=2：1)精製，而得到目標物2.68g(產率55%)。 5-methyl-3-(2,2,2-trifluoroethylthio)-1H-1,2,4-triazole 3.00g (15.2mmol), 3,4-difluorobenzaldehyde 3.24g A mixture of (22.8 mmol), 3.15 g (22.8 mmol) of potassium carbonate and 18 mL of acetonitrile was heated to reflux for 2.5 hours. After leaving to cool at room temperature, ethyl acetate and n-hexane were added and the insoluble material was filtered through celite. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1) to obtain 2.68 g of the target product (yield 55%).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：2.44(3H,d),3.86(2H,q),7.70(1H,t),7.79-7.86(2H,M),10.06(1H,s) 1 H-NMR data (400MHz, CDCl 3 /TMS δ (ppm)): 2.44 (3H, d), 3.86 (2H, q), 7.70 (1H, t), 7.79-7.86 (2H, M), 10.06 ( 1H,s)

(3){3-氟-4-[5-甲基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***-1-基]苯基}甲醇(本發明之化合物號碼：D-2033)的製造 (3){3-fluoro-4-[5-methyl-3-(2,2,2-trifluoroethylthio)-1H-1,2,4-triazol-1-yl]phenyl }Manufacture of methanol (Compound No. of the present invention: D-2033)

在冰冷下將3-氟-4-[5-甲基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***-1-基]苯甲醛2.68g(8.39mmol)的四氫呋喃溶液10mL添加至氫化硼鈉0.44g(12mmol)的四氫呋喃溶液10mL，並攪拌2小時。反應結束後，將1N鹽酸添加至反應溶液中以使過剩的氫化硼鈉分解。然後以乙酸乙酯進行萃取，以飽和碳酸氫鈉水溶液、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=1：2)精製，而得到目標物2.07g(產率77%)。 Under ice cooling, 3-fluoro-4-[5-methyl-3-(2,2,2-trifluoroethylthio)-1H-1,2,4-triazol-1-yl]benzaldehyde 2.68 g (8.39 mmol) of tetrahydrofuran solution 10 mL was added to 0.44 g (12 mmol) of sodium borohydride tetrahydrofuran solution 10 mL and stirred for 2 hours. After the reaction was completed, 1N hydrochloric acid was added to the reaction solution to decompose excess sodium borohydride. Then, extraction was performed with ethyl acetate, and the organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 2) to obtain 2.07 g of the target product (yield 77%).

1H-NMR資料(300MHz,CDCl3/TMS δ(ppm))：2.37(3H,d),3.84(2H,q),4.79(2H,s),7.22-7.33(2H,M),7.42(1H,t) 1 H-NMR data (300MHz, CDCl 3 /TMS δ(ppm)): 2.37(3H,d), 3.84(2H,q),4.79(2H,s),7.22-7.33(2H,M),7.42( 1H,t)

(4)1-[4-(氯甲基)-2-氟苯基]-5-甲基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***(本發明之化合物號碼：D-2034)的製造 (4) 1-[4-(chloromethyl)-2-fluorophenyl]-5-methyl-3-(2,2,2-trifluoroethylthio)-1H-1,2,4 -Manufacture of triazole (Compound No. of the present invention: D-2034)

於室溫下將三苯基膦3.38g(12.9mmol)添加至{3-氟-4-[5-甲基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***-1-基]苯基}甲醇2.07g(6.44mmol)、四氯化碳7.90g(51.4mmol)及四氫呋喃20mL之混合物，於50℃攪拌3小時後，進一步加熱迴流2小時。於室溫下放置冷卻後，添加二異丙基醚與乙酸乙酯並以矽藻土過濾不溶物。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=2：1)精製，而得到目標物1.68g(產率77%)。 3.38g (12.9mmol) of triphenylphosphine was added to {3-fluoro-4-[5-methyl-3-(2,2,2-trifluoroethylthio)-1H-1 at room temperature , 2,4-triazol-1-yl]phenyl}methanol 2.07g (6.44mmol), carbon tetrachloride 7.90g (51.4mmol) and a mixture of tetrahydrofuran 20mL, stirred at 50 ℃ for 3 hours, further heated to reflux 2 hours. After leaving to cool at room temperature, diisopropyl ether and ethyl acetate were added and the insoluble matter was filtered through celite. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1) to obtain 1.68 g of the target product (yield 77%).

1H-NMR資料(300MHz,CDCl3/TMS δ(ppm))：2.38(3H,d),3.84(2H,q),4.61(2H,s),7.30-7.35(2H,M),7.45(1H,t) 1 H-NMR data (300MHz, CDCl 3 /TMS δ (ppm)): 2.38 (3H, d), 3.84 (2H, q), 4.61 (2H, s), 7.30-7.35 (2H, M), 7.45 ( 1H,t)

(5)1-(2-氟-4-甲基苯基)-5-甲基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***(本發明之化合物號碼：D-2028)的製造 (5) 1-(2-fluoro-4-methylphenyl)-5-methyl-3-(2,2,2-trifluoroethylthio)-1H-1,2,4-triazole (Compound No. of the present invention: D-2028)

在冰冷下將氫化硼鈉0.17g(4.5mmol)添加至1-[4-(氯甲基)-2-氟苯基]-5-甲基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***1.55g(4.56mmol)的二甲基亞碸溶液18mL，於室溫下攪拌4小時。然後添加氫化硼鈉0.03g(0.8mmol)並於室溫下攪拌1小時。反應結束後，將1N鹽酸添加至反應溶液中以使過剩的氫化硼鈉分解。然後以乙酸乙酯進行萃取，以水、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑而得到粗製目標物1.60g(產率定量性)。 Under ice cooling, 0.17 g (4.5 mmol) of sodium boron hydride was added to 1-[4-(chloromethyl)-2-fluorophenyl]-5-methyl-3-(2,2,2-trifluoroethane Thiosulfide)-1H-1,2,4-triazole 1.55 g (4.56 mmol) in 18 mL of dimethyl sulfoxide solution and stirred at room temperature for 4 hours. Then, sodium borohydride 0.03 g (0.8 mmol) was added and stirred at room temperature for 1 hour. After the reaction was completed, 1N hydrochloric acid was added to the reaction solution to decompose excess sodium borohydride. Then, extraction was performed with ethyl acetate, and the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.60 g of crude target product (quantitative yield).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：2.48(3H,s),2.52(3H,s),3.84(2H,q),7.10-7.18(2H,M),7.32(1H,t) 1 H-NMR data (400MHz, CDCl 3 /TMS δ (ppm)): 2.48 (3H, s), 2.52 (3H, s), 3.84 (2H, q), 7.10-7.18 (2H, M), 7.32 ( 1H,t)

(6)1-(2-氟-5-碘-4-甲基苯基)-5-甲基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***(本發明之化合物號碼：D-1021)的製造 (6) 1-(2-fluoro-5-iodo-4-methylphenyl)-5-methyl-3-(2,2,2-trifluoroethylthio)-1H-1,2, Production of 4-triazole (Compound No. of the present invention: D-1021)

在冰冷下將N-碘琥珀醯亞胺1.18g(5.24mmol)添加至1-(2-氟-4-甲基苯基)-5-甲基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***1.60g(5.24mmol)的濃硫酸溶液18mL，於冰冷下攪拌7小時。然後，添加N-碘琥珀醯亞胺0.94g(4.2mmol)並於室溫下攪拌17小時。反應結束後，將反應溶液倒入於冰水並以乙酸乙酯進行萃取，以水、1N硫代硫酸鈉水溶液、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑而得到粗製目標物1.93g(產率85%)。 1.18 g (5.24 mmol) of N-iodosuccinimide was added to 1-(2-fluoro-4-methylphenyl)-5-methyl-3-(2,2,2-trifluoro 18 mL of concentrated sulfuric acid solution of 1.60 g (5.24 mmol) of ethylthio)-1H-1,2,4-triazole was stirred under ice cooling for 7 hours. Then, 0.94 g (4.2 mmol) of N-iodosuccinimide was added and stirred at room temperature for 17 hours. After the reaction was completed, the reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water, 1N sodium thiosulfate aqueous solution, and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.93 g of a crude target product (yield 85%).

1H-NMR資料(300MHz,CDCl3/TMS δ(ppm))：2.36(3H,d),2.49(3H,s),3.83(2H,q),7.16(1H,d),7.85(1H,d) 1 H-NMR data (300MHz, CDCl 3 /TMS δ (ppm)): 2.36 (3H, d), 2.49 (3H, s), 3.83 (2H, q), 7.16 (1H, d), 7.85 (1H, d)

(7)4-氟-2-甲基-5-[5-甲基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***-1-基]苯甲腈(本發明之化合物號碼：D-0020)的製造 (7) 4-fluoro-2-methyl-5-[5-methyl-3-(2,2,2-trifluoroethylthio)-1H-1,2,4-triazole-1- Base] Benzonitrile (Compound No. of the present invention: D-0020)

將氰化銅(I)0.80g(8.9mmol)添加至1-(2-氟-5-碘-4-甲基苯基)-5-甲基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***1.93g(4.48mmol)的N,N-二甲基乙醯胺溶液18mL，於100℃攪拌16小時。於室溫下放置冷卻後，添加乙酸乙酯與水並以矽藻土過濾不溶物。以1N鹽酸、水、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=1：1)精製，而得到目標物1.26g(產率85%)。 0.80 g (8.9 mmol) of copper (I) cyanide was added to 1-(2-fluoro-5-iodo-4-methylphenyl)-5-methyl-3-(2,2,2-trifluoro Ethylthio)-1H-1,2,4-triazole 1.93 g (4.48 mmol) in N,N-dimethylacetamide solution 18 mL, and stirred at 100° C. for 16 hours. After leaving to cool at room temperature, ethyl acetate and water were added and the insoluble material was filtered through celite. The organic layer was washed with 1N hydrochloric acid, water, and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1:1) to obtain 1.26 g of the target product (yield 85%).

1H-NMR資料(300MHz,CDCl3/TMS δ(ppm))：2.38(3H,d),2.64(3H,s),3.83(2H,q),7.26(1H,d),7.75(1H,d) 1 H-NMR data (300MHz, CDCl 3 /TMS δ (ppm)): 2.38 (3H, d), 2.64 (3H, s), 3.83 (2H, q), 7.26 (1H, d), 7.75 (1H, d)

(8)4-氟-2-甲基-5-[5-甲基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***-1-基]苯甲酸(本發明之化合物號碼：B-2189)的製造 (8) 4-fluoro-2-methyl-5-[5-methyl-3-(2,2,2-trifluoroethylthio)-1H-1,2,4-triazole-1- ] Benzoic acid (Compound No. of the present invention: B-2189)

於100℃將4-氟-2-甲基-5-[5-甲基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***-1-基]苯甲腈1.26g(3.81mmol)、1,4-二

Figure 108129126-A0202-12-0218-203
烷5mL及60%硫酸36mL之混合物攪拌20.5小時。於室溫下放置冷卻後，添加乙酸乙酯，以水、稀鹽酸、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑而得到粗製目標物1.32g(產率99%)。 4-fluoro-2-methyl-5-[5-methyl-3-(2,2,2-trifluoroethylthio)-1H-1,2,4-triazole-1 at 100°C -Yl]benzonitrile 1.26g (3.81mmol), 1,4-di
Figure 108129126-A0202-12-0218-203
A mixture of 5 mL of alkane and 36 mL of 60% sulfuric acid was stirred for 20.5 hours. After leaving to cool at room temperature, ethyl acetate was added, and the organic layer was washed with water, dilute hydrochloric acid, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.32 g of crude target product (yield 99%).

1H-NMR資料(400MHz,CDCl3/TMS δ(ppm))：2.41(3H,d),2.74(3H,s),3.85(2H,q),7.21(1H,d),8.20(1H,d) 1 H-NMR data (400MHz, CDCl 3 /TMS δ (ppm)): 2.41 (3H, d), 2.74 (3H, s), 3.85 (2H, q), 7.21 (1H, d), 8.20 (1H, d)

(9)4-氟-2-甲基-5-[5-甲基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***-1-基]-N-(2,2,2-三氟乙基)苯甲醯胺的製造 (9) 4-fluoro-2-methyl-5-[5-methyl-3-(2,2,2-trifluoroethylthio)-1H-1,2,4-triazole-1- Radical]-N-(2,2,2-trifluoroethyl)benzamide production

將草醯氯1.31g(10.3mmol)添加至4-氟-2-甲基-5-[5-甲基-3-(2,2,2-三氟乙基硫基)-1H-1,2,4-***-1-基]苯甲酸3.00g(8.59mmol)、N,N-二甲基甲 醯胺0.06g(0.8mmol)及氯仿20mL之混合物，於室溫下攪拌1.5小時。反應結束後，於減壓下餾除溶劑並將殘渣溶解於氯仿20mL，在冰冷下添加至2,2,2-三氟乙胺1.70g(17.2mmol)、三乙胺1.74g(17.2mmol)及氯仿20mL之混合物，於室溫下攪拌一晚。反應結束後，添加氯仿，以水、飽和食鹽水洗淨有機層並藉由無水硫酸鎂進行乾燥。於減壓下餾除溶劑並藉由氧化矽凝膠管柱層析(展開溶劑，正己烷：乙酸乙酯=3：1至1：1)精製，而得到目標物2.91g(產率79%)。 Add 1.31 g (10.3 mmol) of oxalyl chloride to 4-fluoro-2-methyl-5-[5-methyl-3-(2,2,2-trifluoroethylthio)-1H-1, 2,4-triazol-1-yl]benzoic acid 3.00g (8.59mmol), N,N-dimethyl formaldehyde A mixture of 0.06 g (0.8 mmol) of amide and 20 mL of chloroform was stirred at room temperature for 1.5 hours. After the reaction was completed, the solvent was distilled off under reduced pressure and the residue was dissolved in 20 mL of chloroform, and added under ice cooling to 1.70 g (17.2 mmol) of 2,2,2-trifluoroethylamine and 1.74 g (17.2 mmol) of triethylamine. A mixture of 20 mL of chloroform was stirred at room temperature overnight. After the reaction was completed, chloroform was added, the organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 3: 1 to 1:1) to obtain 2.91 g of the target substance (yield 79%) ).

1H-NMR資料(300MHz,CDCl3/TMS δ(ppm))：2.36(3H,d),2.52(3H,s),3.83(2H,q),4.03-4.14(2H,q),6.16(1H,t),7.17(1H,d),7.50(1H,d) 1 H-NMR data (300MHz, CDCl 3 /TMS δ (ppm)): 2.36 (3H, d), 2.52 (3H, s), 3.83 (2H, q), 4.03-4.14 (2H, q), 6.16 ( 1H,t),7.17(1H,d),7.50(1H,d)

將包括前述實施例中之值之依據前述實施例所製造之本發明之化合物[I]的物性值(熔點、折射率及1H-NMR光譜資料)顯示於下述表59至表70中，將包括前述實施例中之值之屬於製造中間物之本發明之化合物[II]的物性值顯示於下述表71至表84中，將包括前述實施例中之值之屬於製造中間物之本發明之化合物[III]的物性值顯示於下述表85至表90中。此外，表中的化合物號碼與記號係與前述相同意義。 The physical property values (melting point, refractive index and 1 H-NMR spectral data) of the compound [I] of the present invention manufactured according to the foregoing examples including the values in the foregoing examples are shown in Tables 59 to 70 below, The physical property values of the compound [II] of the present invention, which includes the values in the foregoing examples, belonging to the production intermediates are shown in the following Tables 71 to 84, and the values of the foregoing embodiments, which belong to the production intermediates, The physical property values of the compound [III] of the invention are shown in Table 85 to Table 90 below. In addition, the compound numbers and symbols in the table have the same meaning as described above.

[表59]

Figure 108129126-A0202-12-0220-126
[Table 59]
Figure 108129126-A0202-12-0220-126

[表60]

Figure 108129126-A0202-12-0221-127
[Table 60]
Figure 108129126-A0202-12-0221-127

[表61]

Figure 108129126-A0202-12-0222-129
[Table 61]
Figure 108129126-A0202-12-0222-129

[表62]

Figure 108129126-A0202-12-0223-130
[Table 62]
Figure 108129126-A0202-12-0223-130

[表63]

Figure 108129126-A0202-12-0224-131
[Table 63]
Figure 108129126-A0202-12-0224-131

[表64]

Figure 108129126-A0202-12-0225-133
[Table 64]
Figure 108129126-A0202-12-0225-133

[表65]

Figure 108129126-A0202-12-0226-134
[Table 65]
Figure 108129126-A0202-12-0226-134

[表66]

Figure 108129126-A0202-12-0227-135
[Table 66]
Figure 108129126-A0202-12-0227-135

[表67]

Figure 108129126-A0202-12-0228-136
[Table 67]
Figure 108129126-A0202-12-0228-136

[表68]

Figure 108129126-A0202-12-0229-139
[Table 68]
Figure 108129126-A0202-12-0229-139

[表69]

Figure 108129126-A0202-12-0230-140
[Table 69]
Figure 108129126-A0202-12-0230-140

[表70]

Figure 108129126-A0202-12-0231-144
[Table 70]
Figure 108129126-A0202-12-0231-144

[表71]

Figure 108129126-A0202-12-0231-145
[Table 71]
Figure 108129126-A0202-12-0231-145

[表72]

Figure 108129126-A0202-12-0232-146
[Table 72]
Figure 108129126-A0202-12-0232-146

[表73]

Figure 108129126-A0202-12-0233-147
[Table 73]
Figure 108129126-A0202-12-0233-147

[表74]

Figure 108129126-A0202-12-0234-148
[Table 74]
Figure 108129126-A0202-12-0234-148

[表75]

Figure 108129126-A0202-12-0235-151
[Table 75]
Figure 108129126-A0202-12-0235-151

[表76]

Figure 108129126-A0202-12-0236-152
[Table 76]
Figure 108129126-A0202-12-0236-152

[表77]

Figure 108129126-A0202-12-0237-153
[Table 77]
Figure 108129126-A0202-12-0237-153

[表78]

Figure 108129126-A0202-12-0238-154
[Table 78]
Figure 108129126-A0202-12-0238-154

[表79]

Figure 108129126-A0202-12-0239-155
[Table 79]
Figure 108129126-A0202-12-0239-155

[表80]

Figure 108129126-A0202-12-0240-156
[Table 80]
Figure 108129126-A0202-12-0240-156

[表81]

Figure 108129126-A0202-12-0241-157
[Table 81]
Figure 108129126-A0202-12-0241-157

[表82]

Figure 108129126-A0202-12-0242-158
[Table 82]
Figure 108129126-A0202-12-0242-158

[表83]

Figure 108129126-A0202-12-0243-159
[Table 83]
Figure 108129126-A0202-12-0243-159

[表84]

Figure 108129126-A0202-12-0244-160
[Table 84]
Figure 108129126-A0202-12-0244-160

[表85]

Figure 108129126-A0202-12-0245-162
[Table 85]
Figure 108129126-A0202-12-0245-162

[表86]

Figure 108129126-A0202-12-0246-163
[Table 86]
Figure 108129126-A0202-12-0246-163

[表87]

Figure 108129126-A0202-12-0247-164
[Table 87]
Figure 108129126-A0202-12-0247-164

[表88]

Figure 108129126-A0202-12-0248-165
[Table 88]
Figure 108129126-A0202-12-0248-165

[表89]

Figure 108129126-A0202-12-0249-166
[Table 89]
Figure 108129126-A0202-12-0249-166

[表90]

Figure 108129126-A0202-12-0250-167
[Table 90]
Figure 108129126-A0202-12-0250-167

接著，具體地說明使用了如上般所製造出之本發明之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物或其農業上所容許之鹽之本發明之有害生物防除劑的製劑例。惟，化合物、添加劑的種類及調配比率並不僅限定於此，可在廣範圍內進行變更。再者，於下述說明中，「份」意指質量份。 Next, the basis of using the 3-(1H-1,2,4-triazol-1-yl)benzamide derivative of the present invention produced as described above or its agriculturally acceptable salt will be specifically described Examples of the preparation of the pest control agent of the invention. However, the types and blending ratios of compounds and additives are not limited to this, and can be changed in a wide range. Furthermore, in the following description, "parts" means parts by mass.

[製劑例1]乳劑 [Formulation Example 1] Emulsion

Figure 108129126-A0202-12-0250-42
Figure 108129126-A0202-12-0250-42

將上述物質均勻地溶解而成為乳劑。 The above-mentioned substances are uniformly dissolved to form an emulsion.

[製劑例2]水合劑 [Formulation Example 2] Hydrating agent

Figure 108129126-A0202-12-0250-43
Figure 108129126-A0202-12-0250-43

Figure 108129126-A0202-12-0251-44
Figure 108129126-A0202-12-0251-44

將上述物質均勻地混合粉碎而成為水合劑。 The above materials are uniformly mixed and pulverized to become a hydrating agent.

[製劑例3]粉劑 [Formulation Example 3] Powder

Figure 108129126-A0202-12-0251-45
Figure 108129126-A0202-12-0251-45

將上述物質均勻地混合粉碎而成為粉劑。 The above materials are uniformly mixed and pulverized into a powder.

[製劑例4]粒劑 [Formulation Example 4] Granules

Figure 108129126-A0202-12-0251-46
Figure 108129126-A0202-12-0251-46

將上述物質均勻地混合粉碎。在此混合物中添加相當於水20份的量並混練，使用擠壓式粒化機加工為14至32網目的粒狀後，進行乾燥而成為粒劑。 The above materials are uniformly mixed and pulverized. To this mixture, an amount equivalent to 20 parts of water was added and kneaded, and processed into granules of 14 to 32 meshes using an extrusion granulator, and then dried to form granules.

[製劑例5]水懸粉劑 [Formulation Example 5] Water suspension powder

Figure 108129126-A0202-12-0251-47
Figure 108129126-A0202-12-0251-47

水 68.98份 68.98 servings of water

藉由高速攪拌機將上述物質混合30分鐘後，藉由濕式粉碎機進行粉碎而成為水懸粉劑。 After mixing the above materials with a high-speed mixer for 30 minutes, it was pulverized by a wet pulverizer to become an aqueous suspension powder.

[製劑例6]顆粒水合劑 [Formulation Example 6] Granule hydrating agent

Figure 108129126-A0202-12-0252-48
Figure 108129126-A0202-12-0252-48

將上述物質混練並擠壓而粒化。藉由流動層乾燥機來乾燥所得到之粒狀物而得到顆粒水合劑。 The above materials are kneaded and squeezed to granulate. The granules obtained were dried by a fluidized bed dryer to obtain granule hydrating agent.

接著，使用試驗例說明本發明之有害生物防除劑所發揮之效果。 Next, the effects of the pest control agent of the present invention will be described using test examples.

[試驗例1]小菜蛾殺蟲活性試驗 [Test Example 1] Pesticide activity test of diamondback moth

將依據製劑例2所調製之水合劑作為有效成分並以水稀釋為500ppm的濃度。將高麗菜葉浸漬於該藥液中，風乾後裝入於塑膠杯。將10隻小菜蛾2齡幼蟲放入其中並上蓋。然後，放置在25℃的恆溫室，於6日後調查死蟲數並藉由數學式1的計算式求取死蟲率。試驗是以1連續方式來進行。 The hydrating agent prepared according to Preparation Example 2 was used as an active ingredient and diluted with water to a concentration of 500 ppm. Korean cabbage leaves were immersed in the drug solution, air-dried and placed in a plastic cup. Ten second-instar larvae of Plutella xylostella were placed in it and covered. Then, it was placed in a constant temperature room at 25°C, and after 6 days, the number of dead insects was investigated and the dead insect rate was obtained by the calculation formula of Mathematical Formula 1. The test is conducted in a continuous manner.

[數學式1]

Figure 108129126-A0202-12-0253-49
[Mathematical formula 1]
Figure 108129126-A0202-12-0253-49

以下係列舉出藉由此試驗顯示出死蟲率90%以上之化合物的化合物號碼。 The following series cite the compound numbers of compounds whose death rate is more than 90% by this test.

A-0018、A-0063、A-0082、A-0104、A-0106、A-0110、A-0113、A-0115、A-0139、A-0176、A-0185、A-0331、A-0386、A-0433、A-0522、A-0539、A-0574、A-0627、A-0648、A-0656、A-0687、A-0689、A-0691、A-0732、A-0745、A-0754、A-0761、A-0773、A-0774、A-1043、A-2196、A-2281、A-2287、A-2331、A-2339、A-2341、A-2345、A-2347、A-2380、A-2381、A-2382、A-2383、A-2384、A-2392、A-2409、A-2410、A-2412、A-2413、A-2420、A-2455、B-0001、B-0077、B-2297、C-0240、D-2011、D-2014、D-2015、D-2016 A-0018, A-0063, A-0082, A-0104, A-0106, A-0110, A-0113, A-0115, A-0139, A-0176, A-0185, A-0331, A- 0386, A-0433, A-0522, A-0539, A-0574, A-0627, A-0648, A-0656, A-0687, A-0689, A-0691, A-0732, A-0745, A-0754, A-0761, A-0773, A-0774, A-1043, A-2196, A-2281, A-2287, A-2331, A-2339, A-2341, A-2345, A- 2347, A-2380, A-2381, A-2382, A-2383, A-2384, A-2392, A-2409, A-2410, A-2412, A-2413, A-2420, A-2455, B-0001, B-0077, B-2297, C-0240, D-2011, D-2014, D-2015, D-2016

[試驗例2]褐飛蝨殺蟲活性試驗 [Test Example 2] Insecticide activity test of brown planthopper

將依據製劑例2所調製之水合劑作為有效成分並以水稀釋為500ppm的濃度。將水稻的發芽稻穀浸漬在該藥液並裝入於塑膠杯。將10隻褐飛蝨2齡幼蟲放入此塑膠杯中並上蓋。然後，放置在25℃的恆溫室，於6日後調查死蟲數並藉由數學式1的計算式來求取死蟲率。試驗是以1連續方式來進行。 The hydrating agent prepared according to Preparation Example 2 was used as an active ingredient and diluted with water to a concentration of 500 ppm. The germinated rice paddy is immersed in the liquid medicine and filled in a plastic cup. Place 10 second-instar larvae of brown planthopper into the plastic cup and cover. Then, it was placed in a constant temperature room at 25°C, and after 6 days, the number of dead insects was investigated and the dead insect rate was determined by the calculation formula of Mathematical Formula 1. The test is conducted in a continuous manner.

使用國際公開第2017/012970號所記載之化合物號碼35作為比較化合物，並進行與上述相同之試驗。比較化合物的結構如下所述。 The compound number 35 described in International Publication No. 2017/012970 was used as a comparative compound, and the same test as above was conducted. The structure of the comparative compound is as follows.

國際公開第2017/012970號 International Publication No. 2017/012970

Figure 108129126-A0202-12-0254-50
Figure 108129126-A0202-12-0254-50

以下列舉出藉由此試驗顯示出死蟲率90%以上之化合物的化合物號碼。 Listed below are the compound numbers of the compounds whose death rate is more than 90% by this test.

A-0001、A-0002、A-0066、A-0075、A-0077、A-0079、A-0082、A-0096、A-0102、A-0110、A-0112、A-0114、A-0121、A-0124、A-0166、A-0176、A-0191、A-0192、A-0230、A-0232、A-0243、A-0244、A-0252、A-0254、A-0261、A-0263、A-0334、A-0335、A-0340、A-0345、A-0346、A-0381、A-0382、A-0393、A-0394、A-0399、A-0432、A-0434、A-0440、A-0443、A-0445、A-0475、A-0476、A-0521、A-0524、A-0529、A-0532、A-0533、A-0538、A-0571、A-0573、A-0574、A-0581、A-0586、A-0617、A-0641、A-0645、A-0647、A-0648、A-0654、A-0655、A-0656、A-0657、A-0658、A-0659、A-0661、A-0669、A-0674、A-0685、A-0728、A-0734、A-0745、A-0754、A-0756、A-0760、A-0766、A-0767、A-1014、A-1020、A-1021、A-1023、A-1024、A-1025、A-1043、A-1044、A-1045、A-1046、A-1096、A-2017、A-2020、A-2056、A-2059、A-2114、A-2117、A-2140、A-2170、A-2184、A-2197、A-2218、A-2240、A-2243、A-2246、A-2281、A-2289、A-2315、A-2316、A-2373、A-2378、A-2382、A-2384、A-2385、A-2386、A-2392、A-2414、A-2415、A-2453、B-0001、B-0257、B-2003、 C-0111、C-0184、C-0238、C-0240、C-2344、D-1004、D-1005、D-2001、D-2002、D-2003、D-2004、D-2011、D-2016、D-2017、D-2022、D-2023 A-0001, A-0002, A-0066, A-0075, A-0077, A-0079, A-0082, A-0096, A-0102, A-0110, A-0112, A-0114, A- 0121, A-0124, A-0166, A-0176, A-0191, A-0192, A-0230, A-0232, A-0243, A-0244, A-0252, A-0254, A-0261, A-0263, A-0334, A-0335, A-0340, A-0345, A-0346, A-0381, A-0382, A-0393, A-0394, A-0399, A-0432, A- 0434, A-0440, A-0443, A-0445, A-0475, A-0476, A-0521, A-0524, A-0529, A-0532, A-0533, A-0538, A-0571, A-0573, A-0574, A-0581, A-0586, A-0617, A-0641, A-0645, A-0647, A-0648, A-0654, A-0655, A-0656, A- 0657, A-0658, A-0659, A-0661, A-0669, A-0674, A-0685, A-0728, A-0734, A-0745, A-0754, A-0756, A-0760, A-0766, A-0767, A-1014, A-1020, A-1021, A-1023, A-1024, A-1025, A-1043, A-1044, A-1045, A-1046, A- 1096, A-2017, A-2020, A-2056, A-2059, A-2114, A-2117, A-2140, A-2170, A-2184, A-2197, A-2218, A-2240, A-2243, A-2246, A-2281, A-2289, A-2315, A-2316, A-2373, A-2378, A-2382, A-2384, A-2385, A-2386, A- 2392, A-2414, A-2415, A-2453, B-0001, B-0257, B-2003, C-0111, C-0184, C-0238, C-0240, C-2344, D-1004, D-1005, D-2001, D-2002, D-2003, D-2004, D-2011, D- 2016, D-2017, D-2022, D-2023

另一方面，比較化合物35(國際公開第2017/012970號所記載)於500ppm的濃度下未顯示出活性。 On the other hand, Comparative Compound 35 (described in International Publication No. 2017/012970) showed no activity at a concentration of 500 ppm.

[試驗例3]二點葉蟎防除效果試驗 [Test Example 3] Experiment on the control effect of Tetranychus urticae

將依據製劑例2所調製之水合劑作為有效成分並以水稀釋為500ppm的濃度。將預先接種了35隻二點葉蟎雌成蟲之大豆苗浸漬在該藥液並風乾。將處理後的大豆苗放置在25℃的恆溫室，於13日後調查雌成蟲的生存蟲數並藉由數學式2的計算式求取防除值。試驗是以1連續方式來進行。 The hydrating agent prepared according to Preparation Example 2 was used as an active ingredient and diluted with water to a concentration of 500 ppm. Soybean seedlings previously inoculated with 35 female Tetranychus urticae female adults were dipped in the drug solution and air-dried. The treated soybean seedlings were placed in a constant temperature room at 25°C, and after 13 days, the number of surviving insects of female adults was investigated and the control value was obtained by the calculation formula of Mathematical Formula 2. The test is conducted in a continuous manner.

[0446] [0446]

Figure 108129126-A0202-12-0255-51
Figure 108129126-A0202-12-0255-51

使用國際公開第2017/012970號所記載之化合物號碼35作為比較化合物，並進行與上述相同之試驗。 The compound number 35 described in International Publication No. 2017/012970 was used as a comparative compound, and the same test as above was conducted.

以下列舉出藉由此試驗顯示出防除值90以上之化合物的化合物號碼。 The following lists the compound numbers of the compounds whose control value shows 90 or more.

A-0001、A-0014、A-0016、A-0029、A-0062、A-0063、A-0066、A-0075、A-0077、A-0079、A-0082、A-0095、A-0096、A-0097、A-0100、A-0101、A-0102、A-0104、A-0105、A-0107、A-0108、A-0110、A-0113、A-0121、A-0123、A-0124、A-0127、A-0135、A-0139、A-0157、A-0178、 A-0180、A-0185、A-0189、A-0190、A-0191、A-0192、A-0195、A-0200、A-0210、A-0211、A-0212、A-0213、A-0214、A-0216、A-0231、A-0232、A-0242、A-0243、A-0244、A-0252、A-0254、A-0255、A-0257、A-0260、A-0261、A-0262、A-0332、A-0334、A-0335、A-0340、A-0341、A-0346、A-0381、A-0382、A-0383、A-0384、A-0385、A-0386、A-0387、A-0388、A-0393、A-0394、A-0398、A-0399、A-0400、A-0432、A-0433、A-0440、A-0443、A-0445、A-0472、A-0473、A-0474、A-0475、A-0476、A-0481、A-0485、A-0521、A-0522、A-0523、A-0524、A-0529、A-0530、A-0531、A-0532、A-0537、A-0538、A-0571、A-0572、A-0573、A-0581、A-0582、A-0583、A-0586、A-0618、A-0620、A-0626、A-0627、A-0635、A-0640、A-0641、A-0645、A-0646、A-0650、A-0654、A-0655、A-0656、A-0657、A-0658、A-0659、A-0661、A-0662、A-0663、A-0665、A-0684、A-0686、A-0697、A-0727、A-0728、A-0732、A-0734、A-0739、A-0745、A-0754、A-0756、A-0763、A-0764、A-0766、A-0767、A-0769、A-0770、A-0772、A-0773、A-0774、A-0775、A-0777、A-0782、A-0783、A-1007、A-1009、A-1014、A-1020、A-1021、A-1022、A-1023、A-1024、A-1025、A-1033、A-1043、A-1044、A-1045、A-1046、A-1095、A-1096、A-2003、A-2006、A-2009、A-2017、A-2018、A-2019、A-2020、A-2032、A-2055、A-2057、A-2059、A-2114、A-2117、A-2140、A-2169、A-2170、A-2183、A-2197、A-2218、A-2239、A-2240、A-2243、A-2246、A-2261、A-2274、A-2294、A-2295、A-2303、A-2315、A-2316、A-2318、A-2324、A-2331、A-2345、A-2352、A-2373、A-2380、A-2381、A-2383、A-2385、A-2386、A-2392、 A-2395、A-2396、A-2397、A-2410、A-2414、A-2416、A-2417、A-2453、A-2455、A-2457、A-2460、C-0111、D-2013 A-0001, A-0014, A-0016, A-0029, A-0062, A-0063, A-0066, A-0075, A-0077, A-0079, A-0082, A-0095, A- 0096, A-0097, A-0100, A-0101, A-0102, A-0104, A-0105, A-0107, A-0108, A-0110, A-0113, A-0121, A-0123, A-0124, A-0127, A-0135, A-0139, A-0157, A-0178, A-0180, A-0185, A-0189, A-0190, A-0191, A-0192, A-0195, A-0200, A-0210, A-0211, A-0212, A-0213, A- 0214, A-0216, A-0231, A-0232, A-0242, A-0243, A-0244, A-0252, A-0254, A-0255, A-0257, A-0260, A-0261, A-0262, A-0332, A-0334, A-0335, A-0340, A-0341, A-0346, A-0381, A-0382, A-0383, A-0384, A-0385, A- 0386, A-0387, A-0388, A-0393, A-0394, A-0398, A-0399, A-0400, A-0432, A-0433, A-0440, A-0443, A-0445, A-0472, A-0473, A-0474, A-0475, A-0476, A-0481, A-0485, A-0521, A-0522, A-0523, A-0524, A-0529, A- 0530, A-0531, A-0532, A-0537, A-0538, A-0571, A-0572, A-0573, A-0581, A-0582, A-0583, A-0586, A-0618, A-0620, A-0626, A-0627, A-0635, A-0640, A-0641, A-0645, A-0646, A-0650, A-0654, A-0655, A-0656, A- 0657, A-0658, A-0659, A-0661, A-0662, A-0663, A-0665, A-0684, A-0686, A-0697, A-0727, A-0728, A-0732, A-0734, A-0739, A-0745, A-0754, A-0756, A-0763, A-0764, A-0766, A-0767, A-0769, A-0770, A-0772, A- 0773, A-0774, A-0775, A-0777, A-0782, A-0783, A-1007, A-1009, A-1014, A-1020, A-1021, A-1022, A-1023, A-1024, A-1025, A-1033, A-1043, A-1044, A-1045, A-1046, A-1095, A-1096, A-2003, A-2006, A-2009, A- 2017, A-2018, A-2019, A-2020, A-2032, A-2055 , A-2057, A-2059, A-2114, A-2117, A-2140, A-2169, A-2170, A-2183, A-2197, A-2218, A-2239, A-2240, A -2243, A-2246, A-2261, A-2274, A-2294, A-2295, A-2303, A-2315, A-2316, A-2318, A-2324, A-2331, A-2345 , A-2352, A-2373, A-2380, A-2381, A-2383, A-2385, A-2386, A-2392, A-2395, A-2396, A-2397, A-2410, A-2414, A-2416, A-2417, A-2453, A-2455, A-2457, A-2460, C-0111, D- 2013

另一方面，比較化合物35(國際公開第2017/012970號所記載)於500ppm的濃度下未顯示出活性。 On the other hand, Comparative Compound 35 (described in International Publication No. 2017/012970) showed no activity at a concentration of 500 ppm.

[試驗例4]根瘤線蟲制線蟲活性試驗 [Test Example 4] Nematode activity test by Rhizobia

將試驗化合物溶解於含有1%的tween20之N,N-二甲基甲醯胺，將此溶液作為有效成分並以水稀釋為20ppm的濃度。將此藥液0.5mL與含有約30隻根瘤線蟲第二期幼蟲之懸浮液0.5mL混合並將有效成分設為10ppm的濃度，放置在25℃的恆溫室。於5日後在顯微鏡下計算生存線蟲數，並藉由數學式3的計算式求取制線蟲活性。試驗是以2連續方式來進行。 The test compound was dissolved in N,N-dimethylformamide containing 1% of tween20, and this solution was used as an active ingredient and diluted with water to a concentration of 20 ppm. 0.5 mL of this drug solution was mixed with 0.5 mL of a suspension containing about 30 second-stage larval nematode larvae and the active ingredient was set to a concentration of 10 ppm, and placed in a constant temperature room at 25°C. After 5 days, the number of viable nematodes was counted under a microscope, and the nematode control activity was obtained by the calculation formula of Mathematical Formula 3. The test was conducted in 2 continuous modes.

Figure 108129126-A0202-12-0257-52
Figure 108129126-A0202-12-0257-52

使用國際公開第2017/012970號所記載之化合物號碼35作為比較化合物並進行與上述相同之試驗。 The compound number 35 described in International Publication No. 2017/012970 was used as a comparative compound and the same test as above was conducted.

以下列舉出藉由此試驗顯示出制線蟲率90%以上之化合物的化合物號碼。 Listed below are the compound numbers of compounds that showed that the nematode production rate was more than 90% through this test.

A-0001、A-0014、A-0016、A-0024、A-0025、A-0029、A-0048、A-0049、A-0052、A-0062、A-0063、A-0066、A-0075、A-0076、A-0077、 A-0079、A-0082、A-0095、A-0101、A-0102、A-0104、A-0105、A-0108、A-0109、A-0110、A-0113、A-0121、A-0122、A-0123、A-0124、A-0135、A-0139、A-0161、A-0165、A-0178、A-0184、A-0185、A-0189、A-0190、A-0191、A-0195、A-0197、A-0200、A-0210、A-0212、A-0216、A-0227、A-0230、A-0242、A-0243、A-0244、A-0252、A-0254、A-0255、A-0257、A-0261、A-0332、A-0335、A-0340、A-0381、A-0382、A-0387、A-0393、A-0394、A-0399、A-0432、A-0433、A-0440、A-0443、A-0476、A-0481、A-0521、A-0522、A-0523、A-0529、A-0530、A-0531、A-0532、A-0538、A-0571、A-0573、A-0581、A-0582、A-0586、A-0620、A-0634、A-0640、A-0641、A-0645、A-0646、A-0649、A-0650、A-0655、A-0656、A-0657、A-0658、A-0659、A-0663、A-0665、A-0683、A-0685、A-0697、A-0727、A-0728、A-0734、A-0745、A-0754、A-0756、A-0762、A-0763、A-0764、A-0766、A-0767、A-0769、A-0773、A-1014、A-1020、A-1021、A-1022、A-1023、A-1024、A-1025、A-1033、A-1043、A-1045、A-1046、A-1078、A-1083、A-1095、A-1096、A-2003、A-2006、A-2018、A-2019、A-2020、A-2055、A-2056、A-2057、A-2058、A-2065、A-2114、A-2117、A-2140、A-2167、A-2169、A-2170、A-2173、A-2183、A-2184、A-2195、A-2196、A-2197、A-2218、A-2228、A-2239、A-2240、A-2243、A-2244、A-2246、A-2261、A-2264、A-2275、A-2281、A-2286、A-2287、A-2291、A-2294、A-2295、A-2315、A-2316、A-2325、A-2331、A-2337、A-2339、A-2340、A-2343、A-2345、A-2346、A-2347、A-2348、A-2352、A-2372、A-2373、A-2374、A-2378、A-2379、A-2380、A-2381、A-2383、A-2392、A-2395、 A-2396、A-2397、A-2409、A-2410、A-2411、A-2412、A-2413、A-2414、A-2415、A-2416、A-2417、A-2419、A-2420、A-2453、A-2455、A-2457、A-2460 A-0001, A-0014, A-0016, A-0024, A-0025, A-0029, A-0048, A-0049, A-0052, A-0062, A-0063, A-0066, A- 0075, A-0076, A-0077, A-0079, A-0082, A-0095, A-0101, A-0102, A-0104, A-0105, A-0108, A-0109, A-0110, A-0113, A-0121, A- 0122, A-0123, A-0124, A-0135, A-0139, A-0161, A-0165, A-0178, A-0184, A-0185, A-0189, A-0190, A-0191, A-0195, A-0197, A-0200, A-0210, A-0212, A-0216, A-0227, A-0230, A-0242, A-0243, A-0244, A-0252, A- 0254, A-0255, A-0257, A-0261, A-0332, A-0335, A-0340, A-0381, A-0382, A-0387, A-0393, A-0394, A-0399, A-0432, A-0433, A-0440, A-0443, A-0476, A-0481, A-0521, A-0522, A-0523, A-0529, A-0530, A-0531, A- 0532, A-0538, A-0571, A-0573, A-0581, A-0582, A-0586, A-0620, A-0634, A-0640, A-0641, A-0645, A-0646, A-0649, A-0650, A-0655, A-0656, A-0657, A-0658, A-0659, A-0663, A-0665, A-0683, A-0685, A-0697, A- 0727, A-0728, A-0734, A-0745, A-0754, A-0756, A-0762, A-0763, A-0764, A-0766, A-0767, A-0769, A-0773, A-1014, A-1020, A-1021, A-1022, A-1023, A-1024, A-1025, A-1033, A-1043, A-1045, A-1046, A-1078, A- 1083, A-1095, A-1096, A-2003, A-2006, A-2018, A-2019, A-2020, A-2055, A-2056, A-2057, A-2058, A-2065, A-2114, A-2117, A-2140, A-2167, A-2169, A-2170, A-2173, A-2183, A-2184, A-2195, A-2196, A-2197, A- 2218, A-2228, A-2239, A-2240, A-2243, A-2244 , A-2246, A-2261, A-2264, A-2275, A-2281, A-2286, A-2287, A-2291, A-2294, A-2295, A-2315, A-2316, A -2325, A-2331, A-2337, A-2339, A-2340, A-2343, A-2345, A-2346, A-2347, A-2348, A-2352, A-2372, A-2373 , A-2374, A-2378, A-2379, A-2380, A-2381, A-2383, A-2392, A-2395, A-2396, A-2397, A-2409, A-2410, A-2411, A-2412, A-2413, A-2414, A-2415, A-2416, A-2417, A-2419, A- 2420, A-2453, A-2455, A-2457, A-2460

另一方面，比較化合物35(國際公開第2017/012970號所記載)於10ppm的濃度下未顯示出活性。 On the other hand, Comparative Compound 35 (described in International Publication No. 2017/012970) showed no activity at a concentration of 10 ppm.

[產業上之可利用性] [Industry availability]

本發明之通式[I]所表示之化合物或其鹽係具有優異的有害生物防除作用，乃有用於作為農藥或殺蟲劑等之有效成分。再者，本發明之通式[II]所表示之化合物以及本發明之通式[III]所表示之化合物係有用於作為通式[I]所表示之化合物的製造中間物。本發明在此等領域等中具有產業上之可利用性。 The compound represented by the general formula [I] of the present invention or a salt thereof has an excellent pest control effect, and is useful as an active ingredient for pesticides, insecticides and the like. Furthermore, the compound represented by the general formula [II] of the present invention and the compound represented by the general formula [III] of the present invention are useful as intermediates for the production of the compound represented by the general formula [I]. The present invention has industrial applicability in these fields and the like.

Figure 108129126-A0202-11-0003-206
Figure 108129126-A0202-11-0003-206

Claims (14)

一種3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物或其農業上所容許之鹽，該3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物係下述通式[I]表示者， A 3-(1H-1,2,4-triazol-1-yl) benzamide derivative or its agriculturally acceptable salt, the 3-(1H-1,2,4-triazole-1 -Yl)benzamide derivatives are represented by the following general formula [I],
Figure 108129126-A0202-13-0001-53
Figure 108129126-A0202-13-0001-53
 式中， In the formula, R1表示氫原子、C1至C6烷基、C1至C6鹵烷基、經R7任意地取代之C1至C6烷基、C3至C6環烷基、C3至C6鹵環烷基、經R8任意地取代之C3至C6環烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、-NH2、-N(R9)R10、-OH、-OR11、-S(=O)2R11、-CH=NOR11或飽和雜環， R 1 represents a hydrogen atom, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl, optionally substituted by R 7 of a C 1 to C 6 alkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, C 3 to C 6 cycloalkyl optionally substituted by R 8 , C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 To C 6 haloalkynyl, -NH 2 , -N(R 9 )R 10 , -OH, -OR 11 , -S(=O) 2 R 11 , -CH=NOR 11, or saturated heterocyclic ring, R2表示氫原子、氰基、C1至C6烷基、C1至C6鹵烷基、經R7任意地取代之C1至C6烷基、C3至C6環烷基、C2至C6烯基、C2至C6炔基、-S(=O)2R11、-C(=O)R11、-C(=O)OR11、-C(=O)NH2、-C(=O)N(R12)R11、-C(=O)N(R12)OR11，或是R1及R2可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 2 represents a hydrogen atom, a cyano group, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a C 1 to C 6 alkyl group optionally substituted by R 7 , a C 3 to C 6 cycloalkyl group, C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, -S(=O) 2 R 11 , -C(=O)R 11 , -C(=O)OR 11 , -C(=O) NH 2 , -C(=O)N(R 12 )R 11 , -C(=O)N(R 12 )OR 11 , or R 1 and R 2 can be bonded to each other to form C 2 to C 6 Alkylene bond, in which case the alkylene bond can contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond can be monovalent by halogen atom or C 1 to C 6 alkyl group Replace or replace more, A表示氧原子或硫原子， A represents an oxygen atom or a sulfur atom, R3表示鹵素原子、氰基、C1至C6烷基、C1至C6鹵烷基、C1至C6烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、-NH2、-N(R9)R10、-C(=O)NH2或-C(=S)NH2， R 3 represents a halogen atom, cyano group, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, C 1 to C 6 alkoxy group, C 1 to C 6 alkylthio group, C 1 to C 6 Alkylsulfinyl, C 1 to C 6 alkylsulfonyl, -NH 2 , -N(R 9 )R 10 , -C(=O)NH 2 or -C(=S)NH 2 , n表示0至3的整數， n represents an integer from 0 to 3, R4表示鹵素原子、氰基、硝基、C1至C6烷基、C1至C6烷氧基C1至C6烷基、C1至C6烷基硫基C1至C6烷基、氰基C1至C6烷基、C1至C6鹵烷基、C3至C6環烷基、C3至C6鹵環烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、-OH、C1至C6烷氧基、C1至C6鹵烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、-NH2或-N(R9)R10， R 4 represents a halogen atom, cyano, nitro, C 1 to C 6 alkyl, C 1 to C 6 alkoxy C 1 to C 6 alkyl, C 1 to C 6 alkylthio C 1 to C 6 Alkyl, cyano C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, -OH, C 1 to C 6 alkoxy, C 1 to C 6 haloalkoxy, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfinyl, C 1 to C 6 haloalkylthio, C 1 to C 6 haloalkyl Sulfonyl, C 1 to C 6 haloalkyl sulfonyl, -NH 2 or -N(R 9 )R 10 , R5表示氫原子、鹵素原子、氰基、硝基、C1至C6烷基、C1至C6鹵烷基、經R13任意地取代之C1至C6烷基、經R13任意地取代之C1至C6鹵烷基、C3至C6環烷基、C3至C6鹵環烷基、經R8任意地取代之C3至C6環烷基、C2至C6烯基、C2至C6鹵烯基、經R13任意地取代之C2至C6烯基、C2至C6炔基、C2至C6鹵炔基、經R13任意地取代之C2至C6炔基、-OH、-OC(=O)R14、-OS(=O)2R14、-OSi(R14)2R12、C1至C6烷氧基、C1至C6鹵烷氧基、經R13任意地取代之C1至C6烷氧基、經R13任意地取代之C1至C6鹵烷氧基、C2至C6烯基氧基、C2至C6鹵烯基氧基、C2至C6炔基氧基、C2至C6鹵炔基氧基、C3至C6環烷基氧基、C3至C6鹵環烷基氧基、無取代或經(Z)p1取代之苯基氧基、芳香族雜環氧基、飽和雜環氧基、-SH、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵 烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、經R13任意地取代之C1至C6烷基硫基、經R13任意地取代之C1至C6烷基亞磺醯基、經R13任意地取代之C1至C6烷基磺醯基、經R13任意地取代之C1至C6鹵烷基硫基、經R13任意地取代之C1至C6鹵烷基亞磺醯基、經R13任意地取代之C1至C6鹵烷基磺醯基、C2至C6烯基硫基、C2至C6烯基亞磺醯基、C2至C6烯基磺醯基、C2至C6鹵烯基硫基、C2至C6鹵烯基亞磺醯基、C2至C6鹵烯基磺醯基、C2至C6炔基硫基、C2至C6炔基亞磺醯基、C2至C6炔基磺醯基、C3至C6環烷基硫基、C3至C6環烷基亞磺醯基、C3至C6環烷基磺醯基、無取代或經(Z)p1取代之苯基硫基、無取代或經(Z)p1取代之苯基亞磺醯基、無取代或經(Z)p1取代之苯基磺醯基、芳香族雜環硫基、芳香族雜環亞磺醯基、芳香族雜環磺醯基、飽和雜環硫基、飽和雜環亞磺醯基、飽和雜環磺醯基、-NH2、-N(R12)R14、-N(R10)C(=O)H、-N(R10)C(=O)R14、-N(R10)C(=O)OR14、-N(R10)C(=O)NH2、-N(R10)C(=O)N(R12)R14、-N(R10)C(=O)N(R12)OR14、-N(R10)C(=S)NH2、-N(R10)C(=S)N(R12)R14、-N(R10)S(=O)2R14、-N(R10)S(=O)2NH2、-N(R10)S(=O)2N(R12)R14、-C(=O)H、-C(=O)R14、-C(=O)OH、-C(=O)OR14、-C(=O)NH2、-C(=O)N(R12)R14、-C(=O)N(R12)OR14、-C(R15)=NOH或-C(R15)=NOR14， R 5 represents a hydrogen atom, a halogen atom, cyano, nitro, C 1 to C 6 -alkyl, C 1 to C 6 haloalkyl, optionally substituted with R of C 13 1 to C 6 alkyl, R 13 the optionally substituted with a C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, optionally substituted with R of C 8 3 to C 6 cycloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl group, with R optionally substituted with of C 13 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, by R 13 Optionally substituted C 2 to C 6 alkynyl, -OH, -OC(=O)R 14 , -OS(=O) 2 R 14 , -OSi(R 14 ) 2 R 12 , C 1 to C 6 alkane group, C 1 to C 6 haloalkoxy, optionally substituted by R 13 of a C 1 to C 6 alkoxy, optionally substituted by R 13 of a C 1 to C 6 haloalkoxy, C 2 to C 6 alkenyloxy, C 2 to C 6 haloalkenyloxy, C 2 to C 6 alkynyloxy, C 2 to C 6 haloalkynyloxy, C 3 to C 6 cycloalkyloxy, C 3 to C 6 halocycloalkyloxy, unsubstituted or substituted (Z)p 1 phenyloxy, aromatic heterocyclic oxy, saturated heterocyclic oxy, -SH, C 1 to C 6 alkyl Thio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 haloalkylthio, C 1 to C 6 haloalkylsulfinyl, a C 1 to C 6 haloalkyl sulfo acyl, optionally substituted by R 13 of a C 1 to C 6 alkylthio, optionally substituted by R of C 13 1 to C 6 alkylsulfinyl acyl, with R 13 of optionally substituted a C 1 to C 6 alkylsulfonyl group, optionally substituted by R of C 13 1 to C 6 haloalkyl group, optionally substituted by R of C 13 1 to C 6 alkylsulfinyl halo Sulfonyl, C 1 to C 6 haloalkyl sulfonyl optionally substituted by R 13 , C 2 to C 6 alkenylthio, C 2 to C 6 alkenylsulfinyl, C 2 to C 6 Alkenylsulfonyl, C 2 to C 6 haloalkenylthio, C 2 to C 6 haloalkenylsulfinyl, C 2 to C 6 haloalkenylsulfonyl, C 2 to C 6 alkynylsulfide group, C 2 to C 6 alkynyl alkylsulfinyl acyl, C 2 to C 6 alkynyl group sulfo acyl, C 3 to C 6 cycloalkyl group, C 3 to C 6 cycloalkyl acyl alkylsulfinyl, C 3 to C 6 cycloalkylsulfonyl, unsubstituted or substituted with (Z)p 1 phenylthio, unsubstituted or substituted with (Z)p 1 phenylsulfinyl, unsubstituted or substituted ( Z) P 1 substituted phenylsulfonyl, aromatic heterocyclic sulfenyl, aromatic heterocyclic sulfenyl, aromatic heterocyclic sulfonyl, saturated heterocyclic sulfenyl, saturated heterocyclic sulfenyl, Saturated heterocyclic sulfonyl, -NH 2 , -N(R 12 )R 14 , -N(R 10 )C(=O)H, -N(R 10 )C(=O )R 14 , -N(R 10 )C(=O)OR 14 , -N(R 10 )C(=O)NH 2 , -N(R 10 )C(=O)N(R 12 )R 14 , -N(R 10 )C(=O)N(R 12 )OR 14 , -N(R 10 )C(=S)NH 2 , -N(R 10 )C(=S)N(R 12 ) R 14 , -N(R 10 )S(=O) 2 R 14 , -N(R 10 )S(=O) 2 NH 2 , -N(R 10 )S(=O) 2 N(R 12 ) R 14 , -C(=O)H, -C(=O)R 14 , -C(=O)OH, -C(=O)OR 14 , -C(=O)NH 2 , -C(= O)N(R 12 )R 14 , -C(=O)N(R 12 )OR 14 , -C(R 15 )=NOH or -C(R 15 )=NOR 14 , R6表示氫原子、鹵素原子、氰基、硝基、C1至C6烷基、C1至C6鹵烷基、經R7任意地取代之C1至C6烷基、C3至C6環烷基、C3至C6鹵環烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、-OH、C1至C6烷氧基、C1至C6鹵烷氧基、經R7任意地取代之C1至C6烷氧基、C2至C6烯基氧基、C2至C6鹵烯基氧基、C2至C6炔基氧基、C2至C6鹵炔 基氧基、C3至C6環烷基氧基、C3至C6鹵環烷基氧基、-SH、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、C2至C6烯基硫基、C2至C6烯基亞磺醯基、C2至C6烯基磺醯基、C2至C6炔基硫基、C2至C6炔基亞磺醯基、C2至C6炔基磺醯基、C3至C6環烷基硫基、C3至C6環烷基亞磺醯基、C3至C6環烷基磺醯基、-NH2、-N(R12)R14、-N(R10)C(=O)H、-N(R10)C(=O)R14、-N(R10)C(=O)OR14、-N(R10)C(=O)NH2、-N(R10)C(=O)N(R12)R14、-N(R10)C(=O)N(R12)OR14、-N(R10)C(=S)NH2、-N(R10)C(=S)N(R12)R14、-N(R10)S(=O)2R14、-N(R10)S(=O)2NH2、-N(R10)S(=O)2N(R12)R14、-N=C(R12)R14、-N=C(R15)N(R12)R14、-NHC(R15)=NOR14、-N=S(R14)R12、-N=S(=O)(R14)R12、-N(R10)NH2、-N(R10)N(R12)R14、-N(R10)N(R10)C(=O)H、-N(R10)N(R10)C(=O)R14、-N(R10)N(R10)C(=O)OR14、-N(R10)N(R10)S(=O)2R14、-C(=O)H、-C(=O)R14、-C(R15)=NOH、-C(R15)=NOR14、-C(=O)OH、-C(=O)OR14、-C(=O)NH2或-C(=O)N(R12)R11， R 6 represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a C 1 to C 6 alkyl group optionally substituted by R 7 , a C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, -OH, C1 to C 6 alkoxy group, C 1 to C 6 haloalkoxy, optionally substituted by R 7 of a C 1 to C 6 alkoxy, C 2 to C 6 alkenyloxy, C 2 to C 6 haloalkenyloxy, C 2 to C 6 alkynyloxy, C 2 to C 6 haloalkynyloxy, C 3 to C 6 cycloalkyloxy, C 3 to C 6 halocycloalkyloxy Group, -SH, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 haloalkylthio, C 1 to C 6 haloalkylsulfinyl, C 1 to C 6 haloalkylsulfonyl, C 2 to C 6 alkenylthio, C 2 to C 6 alkenylsulfinyl, C 2 to C 6 alkenylsulfonyl, C 2 to C 6 alkynylsulfanyl, C 2 to C 6 alkynylsulfinyl, C 2 to C 6 alkynylsulfonyl, C 3 to C 6 cycloalkylsulfanyl , C 3 to C 6 cycloalkylsulfinyl, C 3 to C 6 cycloalkylsulfinyl, -NH 2 , -N(R 12 )R 14 , -N(R 10 )C(=O) H, -N(R 10 )C(=O)R 14 , -N(R 10 )C(=O)OR 14 , -N(R 10 )C(=O)NH 2 , -N(R 10 ) C(=O)N(R 12 )R 14 , -N(R 10 )C(=O)N(R 12 )OR 14 , -N(R 10 )C(=S)NH 2 , -N(R 10 )C(=S)N(R 12 )R 14 , -N(R 10 )S(=O) 2 R 14 , -N(R 10 )S(=O) 2 NH 2 , -N(R 10 )S(=O) 2 N(R 12 )R 14 , -N=C(R 12 )R 14 , -N=C(R 15 )N(R 12 )R 14 , -NHC(R 15 )=NOR 14 , -N=S(R 14 )R 12 , -N=S(=O)(R 14 )R 12 , -N(R 10 )NH 2 , -N(R 10 )N(R 12 )R 14 , -N(R 10 )N(R 10 )C(=O)H, -N(R 10 )N(R 10 )C(=O)R 14 , -N(R 10 )N(R 10 )C (=O)OR 14 , -N(R 10 )N(R 10 )S(=O) 2 R 14 , -C(=O)H, -C(=O) R 14 , -C(R 15 )=NOH, -C(R 15 )=NOR 14 , -C(=O)OH, -C(=O)OR 14 , -C(=O)NH 2 or -C (=O)N(R 12 )R 11 , R7表示氰基、C3至C6環烷基、C3至C6鹵環烷基、-OH、C1至C6烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、-C(=O)OH、-C(=O)OR11、-C(=O)NH2或-C(=O)N(R12)R11， R 7 represents cyano, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, -OH, C 1 to C 6 alkoxy, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, -C(=O)OH, -C(=O)OR 11 , -C(=O)NH 2 or -C(= O)N(R 12 )R 11 , R8表示氰基、C1至C6烷基、C1至C6鹵烷基、C3至C6環烷基、C3至C6鹵環烷基、-C(=O)OR11、-C(=O)NH2或-C(=O)N(R12)R11， R 8 represents cyano, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, -C(=O)OR 11 , -C(=O)NH 2 or -C(=O)N(R 12 )R 11 , R9表示C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6炔基、C3至C6環烷基、-C(=O)H、-C(=O)R11、-C(=O)OR11、-C(=O)NH2、-C(=O)N(R12)R11或-S(=O)2R11， R 9 represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 3 to C 6 cycloalkyl, -C(=O )H, -C(=O)R 11 , -C(=O)OR 11 , -C(=O)NH 2 , -C(=O)N(R 12 )R 11 or -S(=O) 2 R 11 , R10表示氫原子、C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6炔基、C3至C6環烷基、-C(=O)R11、-C(=O)OR11或-S(=O)2R11，或是R9及R10可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 10 represents a hydrogen atom, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 3 to C 6 cycloalkyl, -C (=O)R 11 , -C(=O)OR 11 or -S(=O) 2 R 11 , or R 9 and R 10 may be bonded to each other to form a C 2 to C 6 alkylene bond, At this time, the alkylene bond may contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond may be mono- or multi-substituted by a halogen atom or a C 1 to C 6 alkyl group, R11表示C1至C6烷基、C1至C6鹵烷基、C1至C6烷氧基C1至C6烷基、C1至C6烷基硫C1至C6烷基、氰基C1至C6烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基或C3至C6鹵環烷基， R 11 represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy C 1 to C 6 alkyl, C 1 to C 6 alkyl sulfur C 1 to C 6 alkyl Group, cyano C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl or C 3 to C 6 halocycloalkyl, R12表示氫原子、氰基、C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基或C3至C6鹵環烷基，或是R11及R12可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 12 represents a hydrogen atom, cyano group, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, C 2 to C 6 alkenyl group, C 2 to C 6 haloalkenyl group, C 2 to C 6 alkynyl group , C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl or C 3 to C 6 halocycloalkyl, or R 11 and R 12 may be bonded to each other to form C 2 to C 6 alkylene Base bond, this alkylene bond may contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond may be mono-substituted by halogen atom or C 1 to C 6 alkyl group or Replace more, R13表示氰基、C3至C6環烷基、C3至C6鹵環烷基、-OH、-OR14、-OC(=O)R14、-OS(=O)2R14、-OSi(R14)2R12、-SH、-SR14、-S(=O)R14、-S(=O)2R14、-S(=O)2N(R12)R14、-NH2、-N(R12)R14、-N(R10)C(=O)H、-N(R10)C(=O)R14、-N(R10)C(=O)OR14、-N(R10)C(=O)NH2、-N(R10)C(=O)N(R12)R14、-N(R10)C(=O)N(R12)OR14、-N(R10)C(=S)NH2、-N(R10)C(=S)N(R12)R14、-N(R10)S(=O)2R14、-N(R10)S(=O)2NH2、-N(R10)S(=O)2N(R12)R14、-C(=O)H、-C(=O)R14、-C(=O)OH、-C(=O)OR14、-C(=O)NH2、-C(=O)N(R12)R14、-C(=S)NH2、-C(=S)N(R12)R14、-C(R15)=NOH、-C(R15) =NOR14、-Si(R14)2R12、無取代或經(Z)p1取代之苯基、芳香族雜環或飽和雜環， R 13 represents cyano, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, -OH, -OR 14 , -OC(=O)R 14 , -OS(=O) 2 R 14 , -OSi(R 14 ) 2 R 12 , -SH, -SR 14 , -S(=O)R 14 , -S(=O) 2 R 14 , -S(=O) 2 N(R 12 )R 14 , -NH 2 , -N(R 12 )R 14 , -N(R 10 )C(=O)H, -N(R 10 )C(=O)R 14 , -N(R 10 )C( =O)OR 14 , -N(R 10 )C(=O)NH 2 , -N(R 10 )C(=O)N(R 12 )R 14 , -N(R 10 )C(=O) N(R 12 )OR 14 , -N(R 10 )C(=S)NH 2 , -N(R 10 )C(=S)N(R 12 )R 14 , -N(R 10 )S(= O) 2 R 14 , -N(R 10 )S(=O) 2 NH 2 , -N(R 10 )S(=O)2N(R 12 )R 14 , -C(=O)H, -C (=O)R 14 , -C(=O)OH, -C(=O)OR 14 , -C(=O)NH 2 , -C(=O)N(R 12 )R 14 , -C( =S)NH 2 , -C(=S)N(R 12 )R 14 , -C(R 15 )=NOH, -C(R 15 ) =NOR 14 , -Si(R 14 ) 2 R 12 , none Phenyl, aromatic heterocycle or saturated heterocycle substituted or substituted by (Z)p 1 , R14表示C1至C6烷基、C1至C6鹵烷基、C1至C6烷氧基C1至C6烷基、C1至C6烷基硫C1至C6烷基、氰基C1至C6烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基、C3至C6鹵環烷基、無取代或經(Z)p1取代之苯基、無取代或經(Z)p1取代之苯基C1至C6烷基、芳香族雜環、芳香族雜環C1至C6烷基、飽和雜環或飽和雜環C1至C6烷基，或是R12及R14可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 14 represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy C 1 to C 6 alkyl, C 1 to C 6 alkyl sulfur C 1 to C 6 alkyl Group, cyano C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, unsubstituted or substituted with (Z)p 1 phenyl, unsubstituted or substituted with (Z)p 1 phenyl C 1 to C 6 alkyl, Aromatic heterocycle, aromatic heterocycle C 1 to C 6 alkyl, saturated heterocycle or saturated heterocycle C 1 to C 6 alkyl, or R 12 and R 14 may be bonded to each other to form C 2 to C 6 alkylene bond, in which case the alkylene bond can contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond can be performed by a halogen atom or a C 1 to C 6 alkyl group Single or multiple substitution, R15表示氫原子、鹵素原子、-NH2、氰基、C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基或C3至C6鹵環烷基，或是R14及R15可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 15 represents a hydrogen atom, a halogen atom, -NH 2 , cyano, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl or C 3 to C 6 halocycloalkyl, or R 14 and R 15 may be bonded to each other to form C 2 to C 6 alkylene bond, in which case the alkylene bond can contain 1 oxygen atom, sulfur atom or nitrogen atom, and C 2 to C 6 alkylene bond can be through halogen atom or C 1 to C 6 alkyl groups are mono- or poly-substituted, Z表示鹵素原子、氰基、硝基、C1至C6烷基、C1至C6鹵烷基、-OH、C1至C6烷氧基、C1至C6鹵烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、-NH2、單(C1至C6烷基)胺基、二(C1至C6烷基)胺基、C1至C6烷基羰基胺基、N-(C1至C6烷基羰基)-N-(C1至C6烷基)胺基、C1至C6烷氧基羰基胺基、N-(C1至C6烷氧基羰基)-N-(C1至C6烷基)胺基、C1至C6烷基磺醯基胺基、N-(C1至C6烷基磺醯基)-N-(C1至C6 烷基)胺基、C1至C6鹵烷基磺醯基胺基、N-(C1至C6鹵烷基磺醯基)-N-(C1至C6烷基)胺基、-C(=O)NH2、單(C1至C6烷基)胺基羰基、二(C1至C6烷基)胺基羰基、單(C1至C6鹵烷基)胺基羰基或苯基， Z represents halogen atom, cyano group, nitro group, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, -OH, C 1 to C 6 alkoxy group, C 1 to C 6 haloalkoxy group, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 haloalkylthio, C 1 to C 6 halo Alkylsulfinyl, C 1 to C 6 haloalkylsulfonyl, -NH 2 , mono(C 1 to C 6 alkyl)amino, di(C 1 to C 6 alkyl)amino, C 1 to C 6 alkylcarbonylamino, N-(C 1 to C 6 alkylcarbonyl)-N-(C 1 to C 6 alkyl)amino, C 1 to C 6 alkoxycarbonylamino, N -(C 1 to C 6 alkoxycarbonyl)-N-(C 1 to C 6 alkyl)amino, C 1 to C 6 alkylsulfonylamino, N-(C 1 to C 6 alkyl) Sulfonyl)-N-(C 1 to C 6 alkyl)amino, C 1 to C 6 haloalkylsulfonylamino, N-(C 1 to C 6 haloalkylsulfonyl)-N -(C 1 to C 6 alkyl)amino, -C(=O)NH 2 , mono(C 1 to C 6 alkyl)aminocarbonyl, di(C 1 to C 6 alkyl)aminocarbonyl, Mono(C 1 to C 6 haloalkyl)aminocarbonyl or phenyl, 芳香族雜環表示下列者 Aromatic heterocycle means the following
Figure 108129126-A0202-13-0007-54
Figure 108129126-A0202-13-0007-54
 飽和雜環表示下列者 Saturated heterocycle means the following
Figure 108129126-A0202-13-0007-55
Figure 108129126-A0202-13-0007-55
 p1表示0至5的整數， p 1 represents an integer from 0 to 5, p2表示0至4的整數， p 2 represents an integer from 0 to 4, p3表示0至3的整數， p 3 represents an integer from 0 to 3, p4表示0至2的整數， p 4 represents an integer from 0 to 2, t表示0或1的整數。 t represents an integer of 0 or 1. 一種農藥組成物，該農藥組成物係含有申請專利範圍第1項所述之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物或其農業上所容許之鹽作為有效成分。 A pesticide composition containing 3-(1H-1,2,4-triazol-1-yl)benzamide derivatives described in item 1 of the scope of patent application or agriculturally acceptable The salt as an active ingredient. 如申請專利範圍第2項所述之農藥組成物，該農藥組成物更含有界面活性劑。 As in the pesticide composition described in item 2 of the patent application scope, the pesticide composition further contains a surfactant. 一種有害生物防除劑，該有害生物防除劑係含有申請專利範圍第1項所述之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物或其農業上所容許之鹽作為活性成分。 A pest control agent containing 3-(1H-1,2,4-triazol-1-yl)benzamide derivatives described in item 1 of the patent application scope or its agricultural application Allowable salts are used as active ingredients. 如申請專利範圍第4項所述之有害生物防除劑，該有害生物防除劑為殺蟲劑、殺線蟲劑及殺蟎劑。 The pest control agent as described in item 4 of the patent application scope, the pest control agent is an insecticide, nematicide and acaricide. 如申請專利範圍第5項所述之有害生物防除劑，該有害生物防除劑係對於栽培農園藝用植物之田地或水田中的有害生物具有防除效力。 The pest control agent as described in item 5 of the patent application scope, the pest control agent has a control effect against pests in a field or a paddy field where plants for agriculture and horticulture are cultivated. 如申請專利範圍第6項所述之有害生物防除劑，其中，農園藝用植物係藉由育種法或基因重組技術而被賦有抗性之植物。 The pest control agent as described in item 6 of the patent application scope, wherein the agricultural and horticultural plants are plants that have been conferred resistance by breeding methods or genetic recombination techniques. 一種有害生物的防除方法，該防除方法係使用申請專利範圍第1項所述之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物或其農業上所容許之鹽的有效成分量。 A method for controlling harmful organisms, which uses 3-(1H-1,2,4-triazol-1-yl)benzamide derivatives described in item 1 of the scope of patent application or its agricultural application Allowable amount of active ingredient in salt. 一種有害生物的防除方法，該防除方法係使含有申請專利範圍第1項所述之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物或其農業上所容許之鹽作為有效成分之農藥組成物，同時或分批地作用於農園藝用作物或是欲生育或正在生育農園藝用作物之場所來進行。 A method for controlling harmful organisms, which contains 3-(1H-1,2,4-triazol-1-yl)benzamide derivatives or its agricultural application The allowable salt is used as the active ingredient of the pesticide composition, at the same time or in batches to act on agricultural and horticultural uses or places where they want to have or are growing agricultural and horticultural uses. 如申請專利範圍第8或9項所述之有害生物的防除方法，其中，施用有害生物防除劑之場所為水田、田地、草地、果樹園、非農耕地、溫室、育苗設施、植物工廠中之任一者。 The pest control method as described in item 8 or 9 of the scope of the patent application, where the pest control agent is applied to paddy fields, fields, grasslands, orchards, non-agricultural land, greenhouses, nursery facilities, plant factories Any one. 如申請專利範圍第8至10項中任一項所述之有害生物的防除方法，其中，將申請專利範圍第1項所述之3-(1H-1,2,4-***-1-基)苯甲醯胺衍生物或其農業上所容許之鹽使用為殺蟲劑、殺線蟲劑及殺蟎劑。 The pest control method as described in any of items 8 to 10 of the patent application scope, wherein 3-(1H-1,2,4-triazole-1- Base) benzamide derivatives or their agriculturally acceptable salts are used as insecticides, nematicides and acaricides. 一種有害生物防除劑的使用方法，該使用方法係將申請專利範圍第4至7項中任一項所述之有害生物防除劑使用在對農園藝用作物有害之有害生物的防除。 A method for using a pest control agent, which uses the pest control agent described in any one of items 4 to 7 of the patent application range in the control of pests harmful to agricultural and horticultural use. 一種3-(1H-1,2,4-***-1-基)苯甲酸衍生物或其鹽，該3-(1H-1,2,4-***-1-基)苯甲酸衍生物係下述通式[II]表示者， 3-(1H-1,2,4-triazol-1-yl)benzoic acid derivative or salt thereof, the 3-(1H-1,2,4-triazol-1-yl)benzoic acid derivative It is represented by the following general formula [II],
Figure 108129126-A0202-13-0009-56
Figure 108129126-A0202-13-0009-56
 所表示， Said, 式中， In the formula, K表示-OH、C1至C6烷氧基、C1至C6鹵烷氧基、苯基氧基或是無取代或經(Z)p1取代之苯基C1至C6烷氧基， K represents -OH, C 1 to C 6 alkoxy, C 1 to C 6 haloalkoxy, phenyloxy or unsubstituted or substituted with (Z)p 1 phenyl C 1 to C 6 alkoxy base, R3表示鹵素原子、氰基、C1至C6烷基、C1至C6鹵烷基、C1至C6烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、-NH2、-N(R9)R10、-C(=O)NH2或-C(=S)NH2， R 3 represents a halogen atom, cyano group, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, C 1 to C 6 alkoxy group, C 1 to C 6 alkylthio group, C 1 to C 6 Alkylsulfinyl, C 1 to C 6 alkylsulfonyl, -NH 2 , -N(R 9 )R 10 , -C(=O)NH 2 or -C(=S)NH 2 , n表示0至3的整數， n represents an integer from 0 to 3, R4表示鹵素原子、氰基、硝基、C1至C6烷基、C1至C6烷氧基C1至C6烷基、C1至C6烷基硫C1至C6烷基、氰基C1至C6烷基、C1至C6鹵烷 基、C3至C6環烷基、C3至C6鹵環烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、-OH、C1至C6烷氧基、C1至C6鹵烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、-NH2或-N(R9)R10， R 4 represents a halogen atom, cyano group, nitro group, C 1 to C 6 alkyl group, C 1 to C 6 alkoxy group C 1 to C 6 alkyl group, C 1 to C 6 alkyl sulfur C 1 to C 6 alkyl group Group, cyano C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, C 2 to C 6 alkenyl, C 2 To C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, -OH, C 1 to C 6 alkoxy, C 1 to C 6 haloalkoxy, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfinyl, C 1 to C 6 haloalkylthio, C 1 to C 6 haloalkylsulfinyl Acyl, C 1 to C 6 haloalkylsulfonyl, -NH 2 or -N(R 9 )R 10 , R5表示氫原子、鹵素原子、氰基、硝基、C1至C6烷基、C1至C6鹵烷基、經R13任意地取代之C1至C6烷基、經R13任意地取代之C1至C6鹵烷基、C3至C6環烷基、C3至C6鹵環烷基、經R8任意地取代之C3至C6環烷基、C2至C6烯基、C2至C6鹵烯基、經R13任意地取代之C2至C6烯基、C2至C6炔基、C2至C6鹵炔基、經R13任意地取代之C2至C6炔基、-OH、-OS(=O)2R14、-OSi(R14)2R12、C1至C6烷氧基、C1至C6鹵烷氧基、經R13任意地取代之C1至C6烷氧基、經R13任意地取代之C1至C6鹵烷氧基、C2至C6烯基氧基、C2至C6鹵烯基氧基、C2至C6炔基氧基、C2至C6鹵炔基氧基、C3至C6環烷基氧基、C3至C6鹵環烷基氧基、無取代或經(Z)p1取代之苯基氧基、芳香族雜環氧基、飽和雜環氧基、-SH、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、經R13任意地取代之C1至C6烷基硫基、經R13任意地取代之C1至C6烷基亞磺醯基、經R13任意地取代之C1至C6烷基磺醯基、經R13任意地取代之C1至C6鹵烷基硫基、經R13任意地取代之C1至C6鹵烷基亞磺醯基、經R13任意地取代之C1至C6鹵烷基磺醯基、C2至C6烯基硫基、C2至C6烯基亞磺醯基、C2至C6烯基磺醯基、C2至C6鹵烯基硫基、C2至C6鹵烯基亞磺醯基、C2至C6鹵烯基磺 醯基、C2至C6炔基硫基、C2至C6炔基亞磺醯基、C2至C6炔基磺醯基、C3至C6環烷基硫基、C3至C6環烷基亞磺醯基、C3至C6環烷基磺醯基、無取代或經(Z)p1取代之苯基硫基、無取代或經(Z)p1取代之苯基亞磺醯基、無取代或經(Z)p1取代之苯基磺醯基、芳香族雜環硫基、芳香族雜環亞磺醯基、芳香族雜環磺醯基、飽和雜環硫基、飽和雜環亞磺醯基、飽和雜環磺醯基、-NH2、-N(R12)R14、-N(R10)C(=O)H、-N(R10)C(=O)R14、-N(R10)C(=O)OR14、-N(R10)C(=O)NH2、-N(R10)C(=O)N(R12)R14、-N(R10)C(=O)N(R12)OR14、-N(R10)C(=S)NH2、-N(R10)C(=S)N(R12)R14、-N(R10)S(=O)2R14、-N(R10)S(=O)2NH2、-N(R10)S(=O)2N(R12)R14、-C(=O)H、-C(=O)R14、-C(=O)NH2、-C(=O)N(R12)R14、-C(=O)N(R12)OR14、-C(R15)=NOH或-C(R15)=NOR14， R 5 represents a hydrogen atom, a halogen atom, cyano, nitro, C 1 to C 6 -alkyl, C 1 to C 6 haloalkyl, optionally substituted with R of C 13 1 to C 6 alkyl, R 13 the optionally substituted with a C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, optionally substituted with R of C 8 3 to C 6 cycloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl group, with R optionally substituted with of C 13 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, by R 13 Optionally substituted C 2 to C 6 alkynyl, -OH, -OS(=O) 2 R 14 , -OSi(R 14 ) 2 R 12 , C 1 to C 6 alkoxy, C 1 to C 6 halo alkoxy, optionally substituted by R of C 13 1 to C 6 alkoxy, optionally substituted by R of C 13 1 to C 6 haloalkoxy, C 2 to C 6 alkenyloxy, C 2 to C 6 haloalkenyloxy, C 2 to C 6 alkynyloxy, C 2 to C 6 haloalkynyloxy, C 3 to C 6 cycloalkyloxy, C 3 to C 6 halocycloalkyloxy Group, unsubstituted or substituted (Z)p 1 phenyloxy, aromatic heterocyclic oxy, saturated heterocyclic oxy, -SH, C 1 to C 6 alkylthio, C1 to C 6 alkyl Sulfonyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 haloalkylthio, C 1 to C 6 haloalkylsulfinyl, C 1 to C 6 haloalkylsulfonyl group, optionally substituted with R 13 of a C 1 to C 6 alkylthio, optionally substituted by R of C 13 1 to C 6 alkylsulfinyl acyl, optionally substituted with R 13 a C 1 to C 6 of alkylsulfonyl group, optionally substituted with R of C 13 1 to C 6 haloalkyl group, optionally substituted by R 13 of a C 1 to C 6 alkylsulfinyl halo acyl, optionally substituted by R 13 Of C 1 to C 6 haloalkylsulfonyl, C 2 to C 6 alkenylsulfanyl, C 2 to C 6 alkenylsulfinyl, C 2 to C 6 alkenylsulfonyl, C 2 to C 6 haloalkenylthio, C 2 to C 6 haloalkenylsulfinyl, C 2 to C 6 haloalkenylsulfonyl, C 2 to C 6 alkynylthio, C 2 to C 6 alkynyl Sulfonyl, C 2 to C 6 alkynyl sulfonyl, C 3 to C 6 cycloalkylsulfanyl, C 3 to C 6 cycloalkylsulfinyl, C 3 to C 6 cycloalkylsulfonyl , Unsubstituted or substituted with (Z)p 1 phenylthio, unsubstituted or substituted with (Z)p 1 phenylsulfinyl, unsubstituted or substituted with (Z)p 1 phenylsulfonyl Group, aromatic heterocyclic thio group, aromatic heterocyclic sulfenyl group, aromatic heterocyclic sulfonyl group, saturated heterocyclic sulfenyl group, saturated heterocyclic sulfinyl group, saturated heterocyclic sulfonyl group, -NH 2 , -N(R 12 )R 14 , -N(R 10 )C(=O)H, -N(R 10 )C(=O)R 14 , -N(R 10 )C(=O)OR 14 , -N(R 10 )C(=O)NH 2 , -N(R 10 )C(=O)N(R 12 )R 14 , -N(R 10 )C( =O)N(R 12 )OR 14 , -N(R 10 )C(=S)NH 2 , -N(R 10 )C(=S)N(R 12 )R 14 , -N(R 10 ) S(=O) 2 R 14 , -N(R 10 )S(=O) 2 NH 2 , -N(R 10 )S(=O) 2 N(R 12 )R 14 , -C(=O) H, -C(=O)R 14 , -C(=O)NH 2 , -C(=O)N(R 12 )R 14 , -C(=O)N(R 12 )OR 14 , -C (R 15 )=NOH or -C(R 15 )=NOR 14 , R6表示氫原子、鹵素原子、氰基、硝基、C1至C6烷基、C1至C6鹵烷基、經R7任意地取代之C1至C6烷基、C3至C6環烷基、C3至C6鹵環烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、-OH、C1至C6烷氧基、C1至C6鹵烷氧基、經R7任意地取代之C1至C6烷氧基、C2至C6烯基氧基、C2至C6鹵烯基氧基、C2至C6炔基氧基、C2至C6鹵炔基氧基、C3至C6環烷基氧基、C3至C6鹵環烷基氧基、-SH、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、C2至C6烯基硫基、C2至C6烯基亞磺醯基、C2至C6烯基磺醯基、C2至C6炔基硫基、C2至C6炔基亞磺醯基、C2至C6炔基磺醯基、C3至C6環烷基硫基、C3至C6環烷基亞磺醯基、C3至C6環烷基磺醯基、-NH2、-N(R12)R14、-N(R10)C(=O)H、 -N(R10)C(=O)R14、-N(R10)C(=O)OR14、-N(R10)C(=O)NH2、-N(R10)C(=O)N(R12)R14、-N(R10)C(=O)N(R12)OR14、-N(R10)C(=S)NH2、-N(R10)C(=S)N(R12)R14、-N(R10)S(=O)2R14、-N(R10)S(=O)2NH2、-N(R10)S(=O)2N(R12)R14、-N=C(R12)R14、-N=C(R15)N(R12)R14、-NHC(R15)=NOR14、-N=S(R14)R12、-N=S(=O)(R14)R12、-N(R10)NH2、-N(R10)N(R12)R14、-N(R10)N(R10)C(=O)H、-N(R10)N(R10)C(=O)R14、-N(R10)N(R10)C(=O)OR14、-N(R10)N(R10)S(=O)2R14、-C(=O)H、-C(=O)R14、-C(R15)=NOH、-C(R15)=NOR14、-C(=O)NH2或-C(=O)N(R12)R11， R 6 represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a C 1 to C 6 alkyl group optionally substituted by R 7 , a C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, -OH, a C 1 to C 6 alkoxy group, C 1 to C 6 haloalkoxy, optionally substituted by R 7 of a C 1 to C 6 alkoxy, C 2 to C 6 alkenyloxy, C 2 To C 6 haloalkenyloxy, C 2 to C 6 alkynyloxy, C 2 to C 6 haloalkynyloxy, C 3 to C 6 cycloalkyloxy, C 3 to C 6 halocycloalkyl Oxygen, -SH, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 haloalkylthio, C 1 to C 6 haloalkylsulfinyl, C 1 to C 6 haloalkylsulfonyl, C 2 to C 6 alkenylthio, C 2 to C 6 alkenylsulfinyl, C 2 to C 6 alkenylsulfonyl, C 2 to C 6 alkynylsulfanyl, C 2 to C 6 alkynylsulfinyl, C 2 to C 6 alkynylsulfonyl, C 3 to C 6 cycloalkylsulfide Group, C 3 to C 6 cycloalkylsulfinyl, C 3 to C 6 cycloalkylsulfonyl, -NH 2 , -N(R 12 )R 14 , -N(R 10 )C(=O )H, -N(R 10 )C(=O)R 14 , -N(R 10 )C(=O)OR 14 , -N(R 10 )C(=O)NH 2 , -N(R 10 )C(=O)N(R 12 )R 14 , -N(R 10 )C(=O)N(R 12 )OR 14 , -N(R 10 )C(=S)NH 2 , -N( R 10 )C(=S)N(R 12 )R 14 , -N(R 10 )S(=O) 2 R 14 , -N(R 10 )S(=O) 2 NH 2 , -N(R 10 )S(=O) 2 N(R 12 )R 14 , -N=C(R 12 )R 14 , -N=C(R 15 )N(R 12 )R 14 , -NHC(R 15 )= NOR 14 , -N=S(R 14 )R 12 , -N=S(=O)(R 14 )R 12 , -N(R 10 )NH 2 , -N(R 10 )N(R 12 )R 14 , -N(R 10 )N(R 10 )C(=O)H, -N(R 10 )N(R 10 )C(=O)R 14 , -N(R 10 )N(R 10 ) C(=O)OR 14 , -N(R 10 )N(R 10 )S(=O) 2 R 14 , -C(=O)H, -C(= O)R 14 , -C(R 15 )=NOH, -C(R 15 )=NOR 14 , -C(=O)NH 2 or -C(=O)N(R 12 )R 11 , R7表示氰基、C3至C6環烷基、C3至C6鹵環烷基、-OH、C1至C6烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、-C(=O)NH2或-C(=O)N(R12)R11， R 7 represents cyano, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, -OH, C 1 to C 6 alkoxy, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, -C(=O)NH 2 or -C(=O)N(R 12 )R 11 , R8表示氰基、C1至C6烷基、C1至C6鹵烷基、C3至C6環烷基、C3至C6鹵環烷基、-C(=O)NH2或-C(=O)N(R12)R11， R 8 represents cyano, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, -C(=O)NH 2 Or -C(=O)N(R 12 )R 11 , R9表示C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6炔基、C3至C6環烷基、-C(=O)H、-C(=O)R11、-C(=O)OR11、-C(=O)NH2、-C(=O)N(R12)R11或-S(=O)2R11， R 9 represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 3 to C 6 cycloalkyl, -C(=O )H, -C(=O)R 11 , -C(=O)OR 11 , -C(=O)NH 2 , -C(=O)N(R 12 )R 11 or -S(=O) 2 R 11 , R10表示氫原子、C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6炔基、C3至C6環烷基、-C(=O)R11、-C(=O)OR11或-S(=O)2R11，或是R9及R10可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 10 represents a hydrogen atom, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 3 to C 6 cycloalkyl, -C (=O)R 11 , -C(=O)OR 11 or -S(=O) 2 R 11 , or R 9 and R 10 may be bonded to each other to form a C 2 to C 6 alkylene bond, At this time, the alkylene bond may contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond may be mono- or multi-substituted by a halogen atom or a C 1 to C 6 alkyl group, R11表示C1至C6烷基、C1至C6鹵烷基、C1至C6烷氧基C1至C6烷基、C1至C6烷基硫C1至C6烷基、氰基C1至C6烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基或C3至C6鹵環烷基， R 11 represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy C 1 to C 6 alkyl, C 1 to C 6 alkyl sulfur C 1 to C 6 alkyl Group, cyano C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl or C 3 to C 6 halocycloalkyl, R12表示氫原子、氰基、C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基或C3至C6鹵環烷基，或是R11及R12可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 12 represents a hydrogen atom, cyano group, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, C 2 to C 6 alkenyl group, C 2 to C 6 haloalkenyl group, C 2 to C 6 alkynyl group , C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl or C 3 to C 6 halocycloalkyl, or R 11 and R 12 may be bonded to each other to form C 2 to C 6 alkylene Base bond, this alkylene bond may contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond may be mono-substituted by halogen atom or C 1 to C 6 alkyl group or Replace more, R13表示氰基、C3至C6環烷基、C3至C6鹵環烷基、-OH、-OR14、-OS(=O)2R14、-OSi(R14)2R12、-SH、-SR14、-S(=O)R14、-S(=O)2R14、-S(=O)2N(R12)R14、-NH2、-N(R12)R14、-N(R10)C(=O)H、-N(R10)C(=O)R14、-N(R10)C(=O)OR14、-N(R10)C(=O)NH2、-N(R10)C(=O)N(R12)R14、-N(R10)C(=O)N(R12)OR14、-N(R10)C(=S)NH2、-N(R10)C(=S)N(R12)R14、-N(R10)S(=O)2R14、-N(R10)S(=O)2NH2、-N(R10)S(=O)2N(R12)R14、-C(=O)H、-C(=O)R14、-C(=O)NH2、-C(=O)N(R12)R14、-C(=S)NH2、-C(=S)N(R12)R14、-C(R15)=NOH、-C(R15)=NOR14、-Si(R14)2R12、無取代或經(Z)p1取代之苯基、芳香族雜環或飽和雜環， R 13 represents cyano, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, -OH, -OR 14 , -OS(=O) 2 R 14 , -OSi(R 14 ) 2 R 12 , -SH, -SR 14 , -S(=O)R 14 , -S(=O) 2 R 14 , -S(=O) 2 N(R 12 )R 14 , -NH 2 , -N( R 12 )R 14 , -N(R 10 )C(=O)H, -N(R 10 )C(=O)R 14 , -N(R 10 )C(=O)OR 14 , -N( R 10 )C(=O)NH 2 , -N(R 10 )C(=O)N(R 12 )R 14 , -N(R 10 )C(=O)N(R 12 )OR 14 ,- N(R 10 )C(=S)NH 2 , -N(R 10 )C(=S)N(R 12 )R 14 , -N(R 10 )S(=O) 2 R 14 , -N( R 10 )S(=O) 2 NH 2 , -N(R 10 )S(=O) 2 N(R 12 )R 14 , -C(=O)H, -C(=O)R 14 ,- C(=O)NH 2 , -C(=O)N(R 12 )R 14 , -C(=S)NH 2 , -C(=S)N(R 12 )R 14 , -C(R 15 )=NOH, -C(R 15 )=NOR 14 , -Si(R 14 ) 2 R 12 , unsubstituted or substituted (Z)p 1 phenyl, aromatic heterocycle or saturated heterocycle, R14表示C1至C6烷基、C1至C6鹵烷基、C1至C6烷氧基C1至C6烷基、C1至C6烷基硫C1至C6烷基、氰基C1至C6烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基、C3至C6鹵環烷基、無取代或經(Z)p1取代之苯基、無取代或經(Z)p1取代之苯基C1 至C6烷基、芳香族雜環、芳香族雜環C1至C6烷基、飽和雜環或飽和雜環C1至C6烷基，或是R12及R14可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 14 represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy C 1 to C 6 alkyl, C 1 to C 6 alkyl sulfur C 1 to C 6 alkyl Group, cyano C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, unsubstituted or substituted with (Z)p 1 phenyl, unsubstituted or substituted with (Z)p 1 phenyl C 1 to C 6 alkyl, Aromatic heterocycle, aromatic heterocycle C 1 to C 6 alkyl, saturated heterocycle or saturated heterocycle C 1 to C 6 alkyl, or R 12 and R 14 may be bonded to each other to form C 2 to C 6 alkylene bond, in which case the alkylene bond can contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond can be performed by a halogen atom or a C 1 to C 6 alkyl group Single or multiple substitution, R15表示氫原子、鹵素原子、-NH2、氰基、C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基或C3至C6鹵環烷基，或是R14及R15可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 15 represents a hydrogen atom, a halogen atom, -NH 2 , cyano, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl or C 3 to C 6 halocycloalkyl, or R 14 and R 15 may be bonded to each other to form C 2 to C 6 alkylene bond, in which case the alkylene bond can contain 1 oxygen atom, sulfur atom or nitrogen atom, and C 2 to C 6 alkylene bond can be through halogen atom or C 1 to C 6 alkyl groups are mono- or poly-substituted, Z表示鹵素原子、氰基、硝基、C1至C6烷基、C1至C6鹵烷基、-OH、C1至C6烷氧基、C1至C6鹵烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、-NH2、單(C1至C6烷基)胺基、二(C1至C6烷基)胺基、C1至C6烷基羰基胺基、N-(C1至C6烷基羰基)-N-(C1至C6烷基)胺基、C1至C6烷氧基羰基胺基、N-(C1至C6烷氧基羰基)-N-(C1至C6烷基)胺基、C1至C6烷基磺醯基胺基、N-(C1至C6烷基磺醯基)-N-(C1至C6烷基)胺基、C1至C6鹵烷基磺醯基胺基、N-(C1至C6鹵烷基磺醯基)-N-(C1至C6烷基)胺基、-C(=O)NH2、單(C1至C6烷基)胺基羰基、二(C1至C6烷基)胺基羰基、單(C1至C6鹵烷基)胺基羰基或苯基， Z represents halogen atom, cyano group, nitro group, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, -OH, C 1 to C 6 alkoxy group, C 1 to C 6 haloalkoxy group, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 haloalkylthio, C 1 to C 6 halo Alkylsulfinyl, C 1 to C 6 haloalkylsulfonyl, -NH 2 , mono(C 1 to C 6 alkyl)amino, di(C 1 to C 6 alkyl)amino, C 1 to C 6 alkylcarbonylamino, N-(C 1 to C 6 alkylcarbonyl)-N-(C 1 to C 6 alkyl)amino, C 1 to C 6 alkoxycarbonylamino, N -(C 1 to C 6 alkoxycarbonyl)-N-(C 1 to C 6 alkyl)amino, C 1 to C 6 alkylsulfonylamino, N-(C 1 to C 6 alkyl) Sulfonyl)-N-(C 1 to C 6 alkyl)amino, C 1 to C 6 haloalkylsulfonylamino, N-(C 1 to C 6 haloalkylsulfonyl)-N -(C 1 to C 6 alkyl)amino, -C(=O)NH 2 , mono(C 1 to C 6 alkyl)aminocarbonyl, di(C 1 to C 6 alkyl)aminocarbonyl, Mono(C 1 to C 6 haloalkyl)aminocarbonyl or phenyl, 芳香族雜環表示下列者， Aromatic heterocycle means the following,
Figure 108129126-A0202-13-0015-58
Figure 108129126-A0202-13-0015-58
 飽和雜環表示下列者， Saturated heterocycle means the following,
Figure 108129126-A0202-13-0015-59
Figure 108129126-A0202-13-0015-59
 p1表示0至5的整數， p 1 represents an integer from 0 to 5, p2表示0至4的整數， p 2 represents an integer from 0 to 4, p3表示0至3的整數， p 3 represents an integer from 0 to 3, p4表示0至2的整數， p 4 represents an integer from 0 to 2, t表示0或1的整數。 t represents an integer of 0 or 1. 一種1-苯基-1H-1,2,4-***衍生物或其鹽，該1-苯基-1H-1,2,4-***衍生物為下述通式[III]表示者， A 1-phenyl-1H-1,2,4-triazole derivative or a salt thereof, the 1-phenyl-1H-1,2,4-triazole derivative is represented by the following general formula [III] ,
Figure 108129126-A0202-13-0015-57
Figure 108129126-A0202-13-0015-57
 式中， In the formula, W表示氫原子、鹵素原子或氰基， W represents a hydrogen atom, a halogen atom or a cyano group, R3表示鹵素原子、氰基、C1至C6烷基、C1至C6鹵烷基、C1至C6烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、-NH2、-N(R9)R10、-C(=O)NH2或-C(=S)NH2， R 3 represents a halogen atom, cyano group, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, C 1 to C 6 alkoxy group, C 1 to C 6 alkylthio group, C 1 to C 6 Alkylsulfinyl, C 1 to C 6 alkylsulfonyl, -NH 2 , -N(R 9 )R 10 , -C(=O)NH 2 or -C(=S)NH 2 , n表示0至3的整數， n represents an integer from 0 to 3, R4表示鹵素原子、氰基、硝基、C1至C6烷基、C1至C6烷氧基C1至C6烷基、C1至C6烷基硫C1至C6烷基、氰基C1至C6烷基、C1至C6鹵烷基、C3至C6環烷基、C3至C6鹵環烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、-OH、C1至C6烷氧基、C1至C6鹵烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、-NH2或-N(R9)R10， R 4 represents a halogen atom, cyano group, nitro group, C 1 to C 6 alkyl group, C 1 to C 6 alkoxy group C 1 to C 6 alkyl group, C 1 to C 6 alkyl sulfur C 1 to C 6 alkyl group Group, cyano C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, C 2 to C 6 alkenyl, C 2 To C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, -OH, C 1 to C 6 alkoxy, C 1 to C 6 haloalkoxy, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfinyl, C 1 to C 6 haloalkylthio, C 1 to C 6 haloalkylsulfinyl Acyl, C 1 to C 6 haloalkylsulfonyl, -NH 2 or -N(R 9 )R 10 , R5表示氫原子、鹵素原子、氰基、硝基、C1至C6烷基、C1至C6鹵烷基、經R13任意地取代之C1至C6烷基、經R13任意地取代之C1至C6鹵烷基、C3至C6環烷基、C3至C6鹵環烷基、經R8任意地取代之C3至C6環烷基、C2至C6烯基、C2至C6鹵烯基、經R13任意地取代之C2至C6烯基、C2至C6炔基、C2至C6鹵炔基、經R13任意地取代之C2至C6炔基、-OH、-OC(=O)R14、-OS(=O)2R14、-OSi(R14)2R12、C1至C6烷氧基、C1至C6鹵烷氧基、經R13任意地取代之C1至C6烷氧基、經R13任意地取代之C1至C6鹵烷氧基、C2至C6烯基氧基、C2至C6鹵烯基氧基、C2至C6炔基氧基、C2至C6鹵炔基氧基、C3至C6環烷基氧基、C3至C6鹵環烷基氧基、無取代或經(Z)p1取代之苯基氧基、芳香族雜環氧基、飽和雜環氧基、-SH、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵 烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、經R13任意地取代之C1至C6烷基硫基、經R13任意地取代之C1至C6烷基亞磺醯基、經R13任意地取代之C1至C6烷基磺醯基、經R13任意地取代之C1至C6鹵烷基硫基、經R13任意地取代之C1至C6鹵烷基亞磺醯基、經R13任意地取代之C1至C6鹵烷基磺醯基、C2至C6烯基硫基、C2至C6烯基亞磺醯基、C2至C6烯基磺醯基、C2至C6鹵烯基硫基、C2至C6鹵烯基亞磺醯基、C2至C6鹵烯基磺醯基、C2至C6炔基硫基、C2至C6炔基亞磺醯基、C2至C6炔基磺醯基、C3至C6環烷基硫基、C3至C6環烷基亞磺醯基、C3至C6環烷基磺醯基、無取代或經(Z)p1取代之苯基硫基、無取代或經(Z)p1取代之苯基亞磺醯基、無取代或經(Z)p1取代之苯基磺醯基、芳香族雜環硫基、芳香族雜環亞磺醯基、芳香族雜環磺醯基、飽和雜環硫基、飽和雜環亞磺醯基、飽和雜環磺醯基、-NH2、-N(R12)R14、-N(R10)C(=O)H、-N(R10)C(=O)R14、-N(R10)C(=O)OR14、-N(R10)C(=O)NH2、-N(R10)C(=O)N(R12)R14、-N(R10)C(=O)N(R12)OR14、-N(R10)C(=S)NH2、-N(R10)C(=S)N(R12)R14、-N(R10)S(=O)2R14、-N(R10)S(=O)2NH2、-N(R10)S(=O)2N(R12)R14、-C(=O)H、-C(=O)R14、-C(=O)OH、-C(=O)OR14、-C(=O)NH2、-C(=O)N(R12)R14、-C(=O)N(R12)OR14、-C(R15)=NOH或-C(R15)=NOR14， R 5 represents a hydrogen atom, a halogen atom, cyano, nitro, C 1 to C 6 -alkyl, C 1 to C 6 haloalkyl, optionally substituted with R of C 13 1 to C 6 alkyl, R 13 the optionally substituted with a C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, optionally substituted with R of C 8 3 to C 6 cycloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl group, with R optionally substituted with of C 13 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, by R 13 Optionally substituted C 2 to C 6 alkynyl, -OH, -OC(=O)R 14 , -OS(=O) 2 R 14 , -OSi(R 14 ) 2 R 12 , C 1 to C 6 alkane group, C 1 to C 6 haloalkoxy, optionally substituted by R 13 of a C 1 to C 6 alkoxy, optionally substituted by R 13 of a C 1 to C 6 haloalkoxy, C 2 to C 6 alkenyloxy, C 2 to C 6 haloalkenyloxy, C 2 to C 6 alkynyloxy, C 2 to C 6 haloalkynyloxy, C 3 to C 6 cycloalkyloxy, C 3 to C 6 halocycloalkyloxy, unsubstituted or substituted (Z)p 1 phenyloxy, aromatic heterocyclic oxy, saturated heterocyclic oxy, -SH, C 1 to C 6 alkyl Thio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 haloalkylthio, C 1 to C 6 haloalkylsulfinyl, a C 1 to C 6 haloalkyl sulfo acyl, optionally substituted by R 13 of a C 1 to C 6 alkylthio, optionally substituted by R of C 13 1 to C 6 alkylsulfinyl acyl, with R 13 of optionally substituted a C 1 to C 6 alkylsulfonyl group, optionally substituted by R of C 13 1 to C 6 haloalkyl group, optionally substituted by R of C 13 1 to C 6 alkylsulfinyl halo Sulfonyl, C 1 to C 6 haloalkyl sulfonyl optionally substituted by R 13 , C 2 to C 6 alkenylthio, C 2 to C 6 alkenylsulfinyl, C 2 to C 6 Alkenylsulfonyl, C 2 to C 6 haloalkenylthio, C 2 to C 6 haloalkenylsulfinyl, C 2 to C 6 haloalkenylsulfonyl, C 2 to C 6 alkynylsulfide group, C 2 to C 6 alkynyl alkylsulfinyl acyl, C 2 to C 6 alkynyl group sulfo acyl, C 3 to C 6 cycloalkyl group, C 3 to C 6 cycloalkyl acyl alkylsulfinyl, C 3 to C 6 cycloalkylsulfonyl, unsubstituted or substituted with (Z)p 1 phenylthio, unsubstituted or substituted with (Z)p 1 phenylsulfinyl, unsubstituted or substituted ( Z) P 1 substituted phenylsulfonyl, aromatic heterocyclic sulfenyl, aromatic heterocyclic sulfenyl, aromatic heterocyclic sulfonyl, saturated heterocyclic sulfenyl, saturated heterocyclic sulfenyl, Saturated heterocyclic sulfonyl, -NH 2 , -N(R 12 )R 14 , -N(R 10 )C(=O)H, -N(R 10 )C(=O )R 14 , -N(R 10 )C(=O)OR 14 , -N(R 10 )C(=O)NH 2 , -N(R 10 )C(=O)N(R 12 )R 14 , -N(R 10 )C(=O)N(R 12 )OR 14 , -N(R 10 )C(=S)NH 2 , -N(R 10 )C(=S)N(R 12 ) R 14 , -N(R 10 )S(=O) 2 R 14 , -N(R 10 )S(=O) 2 NH 2 , -N(R 10 )S(=O) 2 N(R 12 ) R 14 , -C(=O)H, -C(=O)R 14 , -C(=O)OH, -C(=O)OR 14 , -C(=O)NH 2 , -C(= O)N(R 12 )R 14 , -C(=O)N(R 12 )OR 14 , -C(R 15 )=NOH or -C(R 15 )=NOR 14 , R6表示氫原子、鹵素原子、氰基、硝基、C1至C6烷基、C1至C6鹵烷基、經R7任意地取代之C1至C6烷基、C3至C6環烷基、C3至C6鹵環烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、-OH、C1至C6烷氧基、C1至C6鹵烷氧基、經R7任意地取代之C1至C6烷氧基、C2至C6烯基氧基、C2至C6鹵烯基氧基、C2至C6炔基氧基、C2至C6鹵炔 基氧基、C3至C6環烷基氧基、C3至C6鹵環烷基氧基、-SH、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、C2至C6烯基硫基、C2至C6烯基亞磺醯基、C2至C6烯基磺醯基、C2至C6炔基硫基、C2至C6炔基亞磺醯基、C2至C6炔基磺醯基、C3至C6環烷基硫基、C3至C6環烷基亞磺醯基、C3至C6環烷基磺醯基、-NH2、-N(R12)R14、-N(R10)C(=O)H、-N(R10)C(=O)R14、-N(R10)C(=O)OR14、-N(R10)C(=O)NH2、-N(R10)C(=O)N(R12)R14、-N(R10)C(=O)N(R12)OR14、-N(R10)C(=S)NH2、-N(R10)C(=S)N(R12)R14、-N(R10)S(=O)2R14、-N(R10)S(=O)2NH2、-N(R10)S(=O)2N(R12)R14、-N=C(R12)R14、-N=C(R15)N(R12)R14、-NHC(R15)=NOR14、-N=S(R14)R12、-N=S(=O)(R14)R12、-N(R10)NH2、-N(R10)N(R12)R14、-N(R10)N(R10)C(=O)H、-N(R10)N(R10)C(=O)R14、-N(R10)N(R10)C(=O)OR14、-N(R10)N(R10)S(=O)2R14、-C(=O)H、-C(=O)R14、-C(R15)=NOH、-C(R15)=NOR14、-C(=O)OH、-C(=O)OR14、-C(=O)NH2或-C(=O)N(R12)R11， R 6 represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a C 1 to C 6 alkyl group optionally substituted by R 7 , a C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, -OH, C1 to C 6 alkoxy group, C 1 to C 6 haloalkoxy, optionally substituted by R 7 of a C 1 to C 6 alkoxy, C 2 to C 6 alkenyloxy, C 2 to C 6 haloalkenyloxy, C 2 to C 6 alkynyloxy, C 2 to C 6 haloalkynyloxy, C 3 to C 6 cycloalkyloxy, C 3 to C 6 halocycloalkyloxy Group, -SH, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 haloalkylthio, C 1 to C 6 haloalkylsulfinyl, C 1 to C 6 haloalkylsulfonyl, C 2 to C 6 alkenylthio, C 2 to C 6 alkenylsulfinyl, C 2 to C 6 alkenylsulfonyl, C 2 to C 6 alkynylsulfanyl, C 2 to C 6 alkynylsulfinyl, C 2 to C 6 alkynylsulfonyl, C 3 to C 6 cycloalkylsulfanyl , C 3 to C 6 cycloalkylsulfinyl, C 3 to C 6 cycloalkylsulfinyl, -NH 2 , -N(R 12 )R 14 , -N(R 10 )C(=O) H, -N(R 10 )C(=O)R 14 , -N(R 10 )C(=O)OR 14 , -N(R 10 )C(=O)NH 2 , -N(R 10 ) C(=O)N(R 12 )R 14 , -N(R 10 )C(=O)N(R 12 )OR 14 , -N(R 10 )C(=S)NH 2 , -N(R 10 )C(=S)N(R 12 )R 14 , -N(R 10 )S(=O) 2 R 14 , -N(R 10 )S(=O) 2 NH 2 , -N(R 10 )S(=O) 2 N(R 12 )R 14 , -N=C(R 12 )R 14 , -N=C(R 15 )N(R 12 )R 14 , -NHC(R 15 )=NOR 14 , -N=S(R 14 )R 12 , -N=S(=O)(R 14 )R 12 , -N(R 10 )NH 2 , -N(R 10 )N(R 12 )R 14 , -N(R 10 )N(R 10 )C(=O)H, -N(R 10 )N(R 10 )C(=O)R 14 , -N(R 10 )N(R 10 )C (=O)OR 14 , -N(R 10 )N(R 10 )S(=O) 2 R 14 , -C(=O)H, -C(=O) R 14 , -C(R 15 )=NOH, -C(R 15 )=NOR 14 , -C(=O)OH, -C(=O)OR 14 , -C(=O)NH 2 or -C (=O)N(R 12 )R 11 , R7表示氰基、C3至C6環烷基、C3至C6鹵環烷基、-OH、C1至C6烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、-C(=O)OH、-C(=O)OR11、-C(=O)NH2或-C(=O)N(R12)R11， R 7 represents cyano, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, -OH, C 1 to C 6 alkoxy, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, -C(=O)OH, -C(=O)OR 11 , -C(=O)NH 2 or -C(= O)N(R 12 )R 11 , R8表示氰基、C1至C6烷基、C1至C6鹵烷基、C3至C6環烷基、C3至C6鹵環烷基、-C(=O)OR11、-C(=O)NH2或-C(=O)N(R12)R11， R 8 represents cyano, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, -C(=O)OR 11 , -C(=O)NH 2 or -C(=O)N(R 12 )R 11 , R9表示C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6炔基、C3至C6環烷基、-C(=O)H、-C(=O)R11、-C(=O)OR11、-C(=O)NH2、-C(=O)N(R12)R11或-S(=O)2R11， R 9 represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 3 to C 6 cycloalkyl, -C(=O )H, -C(=O)R 11 , -C(=O)OR 11 , -C(=O)NH 2 , -C(=O)N(R 12 )R 11 or -S(=O) 2 R 11 , R10表示氫原子、C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6炔基、C3至C6環烷基、-C(=O)R11、-C(=O)OR11或-S(=O)2R11，或是R9及R10可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 10 represents a hydrogen atom, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 3 to C 6 cycloalkyl, -C (=O)R 11 , -C(=O)OR 11 or -S(=O) 2 R 11 , or R 9 and R 10 may be bonded to each other to form a C 2 to C 6 alkylene bond, At this time, the alkylene bond may contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond may be mono- or multi-substituted by a halogen atom or a C 1 to C 6 alkyl group, R11表示C1至C6烷基、C1至C6鹵烷基、C1至C6烷氧基C1至C6烷基、C1至C6烷基硫C1至C6烷基、氰基C1至C6烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基或C3至C6鹵環烷基， R 11 represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy C 1 to C 6 alkyl, C 1 to C 6 alkyl sulfur C 1 to C 6 alkyl Group, cyano C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl or C 3 to C 6 halocycloalkyl, R12表示氫原子、氰基、C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基或C3至C6鹵環烷基，或是R11及R12可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 12 represents a hydrogen atom, cyano group, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, C 2 to C 6 alkenyl group, C 2 to C 6 haloalkenyl group, C 2 to C 6 alkynyl group , C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl or C 3 to C 6 halocycloalkyl, or R 11 and R 12 may be bonded to each other to form C 2 to C 6 alkylene Base bond, this alkylene bond may contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond may be mono-substituted by halogen atom or C 1 to C 6 alkyl group or Replace more, R13表示氰基、C3至C6環烷基、C3至C6鹵環烷基、-OH、-OR14、-OC(=O)R14、-OS(=O)2R14、-OSi(R14)2R12、-SH、-SR14、-S(=O)R14、-S(=O)2R14、-S(=O)2N(R12)R14、-NH2、-N(R12)R14、-N(R10)C(=O)H、-N(R10)C(=O)R14、-N(R10)C(=O)OR14、-N(R10)C(=O)NH2、-N(R10)C(=O)N(R12)R14、-N(R10)C(=O)N(R12)OR14、-N(R10)C(=S)NH2、-N(R10)C(=S)N (R12)R14、-N(R10)S(=O)2R14、-N(R10)S(=O)2NH2、-N(R10)S(=O)2N(R12)R14、-C(=O)H、-C(=O)R14、-C(=O)OH、-C(=O)OR14、-C(=O)NH2、-C(=O)N(R12)R14、-C(=S)NH2、-C(=S)N(R12)R14、-C(R15)=NOH、-C(R15)=NOR14、-Si(R14)2R12、無取代或經(Z)p1取代之苯基、芳香族雜環或飽和雜環， R 13 represents cyano, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, -OH, -OR 14 , -OC(=O)R 14 , -OS(=O) 2 R 14 , -OSi(R 14 ) 2 R 12 , -SH, -SR 14 , -S(=O)R 14 , -S(=O) 2 R 14 , -S(=O) 2 N(R 12 )R 14 , -NH 2 , -N(R 12 )R 14 , -N(R 10 )C(=O)H, -N(R 10 )C(=O)R 14 , -N(R 10 )C( =O)OR 14 , -N(R 10 )C(=O)NH 2 , -N(R 10 )C(=O)N(R 12 )R 14 , -N(R 10 )C(=O) N(R 12 )OR 14 , -N(R 10 )C(=S)NH 2 , -N(R 10 )C(=S)N (R 12 )R 14 , -N(R 10 )S(= O) 2 R 14 , -N(R 10 )S(=O) 2 NH 2 , -N(R 10 )S(=O) 2 N(R 12 )R 14 , -C(=O)H,- C(=O)R 14 , -C(=O)OH, -C(=O)OR 14 , -C(=O)NH 2 , -C(=O)N(R 12 )R 14 , -C (=S)NH 2 , -C(=S)N(R 12 )R 14 , -C(R 15 )=NOH, -C(R 15 )=NOR 14 , -Si(R 14 ) 2 R 12 , Unsubstituted or substituted (Z)p 1 phenyl, aromatic heterocyclic or saturated heterocyclic, R14表示C1至C6烷基、C1至C6鹵烷基、C1至C6烷氧基C1至C6烷基、C1至C6烷基硫C1至C6烷基、氰基C1至C6烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基、C3至C6鹵環烷基、無取代或經(Z)p1取代之苯基、無取代或經(Z)p1取代之苯基C1至C6烷基、芳香族雜環、芳香族雜環C1至C6烷基、飽和雜環或飽和雜環C1至C6烷基，或是R12及R14可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 14 represents C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy C 1 to C 6 alkyl, C 1 to C 6 alkyl sulfur C 1 to C 6 alkyl Group, cyano C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl, C 3 to C 6 halocycloalkyl, unsubstituted or substituted with (Z)p 1 phenyl, unsubstituted or substituted with (Z)p 1 phenyl C 1 to C 6 alkyl, Aromatic heterocycle, aromatic heterocycle C 1 to C 6 alkyl, saturated heterocycle or saturated heterocycle C 1 to C 6 alkyl, or R 12 and R 14 may be bonded to each other to form C 2 to C 6 alkylene bond, in which case the alkylene bond can contain 1 oxygen atom, sulfur atom or nitrogen atom, and the C 2 to C 6 alkylene bond can be performed by a halogen atom or a C 1 to C 6 alkyl group Single or multiple substitution, R15表示氫原子、鹵素原子、-NH2、氰基、C1至C6烷基、C1至C6鹵烷基、C2至C6烯基、C2至C6鹵烯基、C2至C6炔基、C2至C6鹵炔基、C3至C6環烷基或C3至C6鹵環烷基，或是R14及R15可相互地鍵結而形成C2至C6伸烷基鍵，此時此伸烷基鍵可含有1個氧原子、硫原子或氮原子，且C2至C6伸烷基鍵可藉由鹵素原子或C1至C6烷基進行單取代或多取代， R 15 represents a hydrogen atom, a halogen atom, -NH 2 , cyano, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl, C 2 to C 6 alkynyl, C 2 to C 6 haloalkynyl, C 3 to C 6 cycloalkyl or C 3 to C 6 halocycloalkyl, or R 14 and R 15 may be bonded to each other to form C 2 to C 6 alkylene bond, in which case the alkylene bond can contain 1 oxygen atom, sulfur atom or nitrogen atom, and C 2 to C 6 alkylene bond can be through halogen atom or C 1 to C 6 alkyl groups are mono- or poly-substituted, Z表示鹵素原子、氰基、硝基、C1至C6烷基、C1至C6鹵烷基、-OH、C1至C6烷氧基、C1至C6鹵烷氧基、C1至C6烷基硫基、C1至C6烷基亞磺醯基、C1至C6烷基磺醯基、C1至C6鹵烷基硫基、C1至C6鹵烷基亞磺醯基、C1至C6鹵烷基磺醯基、-NH2、單(C1至C6烷基)胺基、二(C1至C6烷 基)胺基、C1至C6烷基羰基胺基、N-(C1至C6烷基羰基)-N-(C1至C6烷基)胺基、C1至C6烷氧基羰基胺基、N-(C1至C6烷氧基羰基)-N-(C1至C6烷基)胺基、C1至C6烷基磺醯基胺基、N-(C1至C6烷基磺醯基)-N-(C1至C6烷基)胺基、C1至C6鹵烷基磺醯基胺基、N-(C1至C6鹵烷基磺醯基)-N-(C1至C6烷基)胺基、-C(=O)NH2、單(C1至C6烷基)胺基羰基、二(C1至C6烷基)胺基羰基、單(C1至C6鹵烷基)胺基羰基或苯基， Z represents halogen atom, cyano group, nitro group, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, -OH, C 1 to C 6 alkoxy group, C 1 to C 6 haloalkoxy group, C 1 to C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 haloalkylthio, C 1 to C 6 halo Alkylsulfinyl, C 1 to C 6 haloalkylsulfonyl, -NH 2 , mono(C 1 to C 6 alkyl)amino, di(C 1 to C 6 alkyl)amino, C 1 to C 6 alkylcarbonylamino, N-(C 1 to C 6 alkylcarbonyl)-N-(C 1 to C 6 alkyl)amino, C 1 to C 6 alkoxycarbonylamino, N -(C 1 to C 6 alkoxycarbonyl)-N-(C 1 to C 6 alkyl)amino, C 1 to C 6 alkylsulfonylamino, N-(C 1 to C 6 alkyl) Sulfonyl)-N-(C 1 to C 6 alkyl)amino, C 1 to C 6 haloalkylsulfonylamino, N-(C 1 to C 6 haloalkylsulfonyl)-N -(C 1 to C 6 alkyl)amino, -C(=O)NH 2 , mono(C 1 to C 6 alkyl)aminocarbonyl, di(C 1 to C 6 alkyl)aminocarbonyl, Mono(C 1 to C 6 haloalkyl)aminocarbonyl or phenyl, 芳香族雜環表示下列者， Aromatic heterocycle means the following,
Figure 108129126-A0202-13-0021-60
Figure 108129126-A0202-13-0021-60
 飽和雜環表示下列者， Saturated heterocycle means the following,
Figure 108129126-A0202-13-0021-61
Figure 108129126-A0202-13-0021-61
 p1表示0至5的整數， p 1 represents an integer from 0 to 5, p2表示0至4的整數， p 2 represents an integer from 0 to 4, p3表示0至3的整數， p 3 represents an integer from 0 to 3, p4表示0至2的整數， p 4 represents an integer from 0 to 2, t表示0或1的整數。 t represents an integer of 0 or 1.
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