CN109305964B - Fungicide hydroximoyl-tetrazole derivatives - Google Patents

Fungicide hydroximoyl-tetrazole derivatives Download PDF

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CN109305964B
CN109305964B CN201710620721.6A CN201710620721A CN109305964B CN 109305964 B CN109305964 B CN 109305964B CN 201710620721 A CN201710620721 A CN 201710620721A CN 109305964 B CN109305964 B CN 109305964B
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CN109305964A (en
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李义涛
熊力
卢辉
林健
刘新烁
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Dongguan dongyangguang pesticide R & D Co., Ltd
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Dongguan Dongyang Guangke Research and Development Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The present invention provides a kind of fungicide hydroximoyl-tetrazole derivatives；Specifically, the present invention relates to oximido-terazole derivatives, their preparation method, and their purposes as fungicide active agents, and its form of Fungicidal composition, and the method for controlling with these compound or compositions plant pathogenic fungi (plant pathogenic fungi especially in plant).

Description

Fungicide hydroximoyl-tetrazole derivatives
Technical field
The present invention relates to oximido (hydroximoyl)-terazole derivatives, their preparation method and their conducts are killed The purposes of fungi activity agent and its form of Fungicidal composition, and phytopathy is controlled with these compound or compositions The method of fungal pathogens (plant pathogenic fungi especially in plant).
Background technique
In Japanese patent application JP 2011012088, the tetrazole radical 9 oxime derivate with following formula chemical structure is disclosed:
Wherein A is substituted or unsubstituted heterocycle；B is a key or substituted or unsubstituted alkylidene；X be replace or Unsubstituted aromatic rings or non-aromatic ring；Y is substituted or unsubstituted aryl.
In PCT Patent Application WO 9929689, the derivative with following formula chemical structure is disclosed:
Wherein HetA indicates that the nitrogenous aromatic rings in substituted or unsubstituted 6 containing 1 or 2 nitrogen-atoms yuan or its benzo are thick Ring-like nitrogenous aromatic rings；HetB indicates substituted or unsubstituted 1,2,3- thiadiazoles -5- base, 1,2,5- thiadiazoles -3- base or 1, 2,5- oxadiazoles -3- base；R1Indicate hydrogen atom or low alkyl group；X represents halogen atom, nitro, hydroxyl, cyano etc.；N indicates 0-3 Integer.
The compound of the present invention is not disclosed in this two patents document.
People pay high attention to always the application of novel pesticide compound in agriculture field, to avoid or prevention and control to active ingredient There is the generation of the bacterial strain of drug resistance.Same people pay high attention to use compounds more higher than known compound activity, mesh Be marked in reduce used in reactive compound amount, maintain at the same time at least with the comparable effect of known compound.This hair It is bright provide one kind have the advantages that said effect or noval chemical compound.
Summary of the invention
The present invention provides formula (I) compound represented, the salt of compound shown in formula (I), N- oxide, metal complex, Metal complexes or (E) and (Z) isomers and their mixture:
Wherein:
Y1、Y2、Y3And Y4Be each independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxyl, alkyl, Alkenyl, alkynyl, alkoxy, alkenyloxy group, alkynyloxy group, aryl, heteroaryl, naphthenic base, heterocycle, aryl alkyl, heteroaryl alkyl, Cycloalkyl-alkyl, heterocyclylalkyl group ,-C (=O)-alkyl ,-C (=O)-alkenyl ,-C (=O)-alkynyl ,-C (=O)-aryl ,-C (=O)-heteroaryl ,-C (=O)-naphthenic base ,-C (=O)-heterocycle ,-C (=O)-O- alkyl ,-C (=O)-O- alkenyl ,-C (=O)-O- alkynyl ,-C (=O)-alkylene-aryl ,-C (=O)-alkenylene-aryl ,-C (=O)-alkylene-heteroaryl ,-C (=O)-alkenylene-heteroaryl ,-C (=O)-alkylene-cycloalkyl ,-C (=O)-alkenylene-naphthenic base ,-C (=O)-alkylene Base-heterocycle ,-C (=O)-alkenylene-heterocycle ,-S (=O)2Alkyl ,-S (=O)2Alkenyl ,-S (=O)2Alkynyl ,-S (=O)2Aryl ,-S (=O)2Heteroaryl ,-S (=O)2Naphthenic base ,-S (=O)2Heterocycle ,-OX or-NRaRb；Wherein Y1、 Y2、Y3And Y4Respectively R is selected from by 1,2,3,4,5,6,7,8,9 or 10 individually optionally1Substituent group replaced；
Each X independently be hydrogen, alkyl, alkenyl, alkynyl ,-C (=O)-alkyl ,-C (=O)-alkenyl ,-C (=O)-alkynyl ,- C (=O)-aryl ,-C (=O)-heteroaryl ,-C (=O)-naphthenic base ,-C (=O)-heterocycle ,-C (=O)-O- alkyl ,-C (= O)-O- alkenyl ,-C (=O)-O- alkynyl ,-S (=O)2Alkyl ,-S (=O)2Alkenyl ,-S (=O)2Alkynyl ,-S (=O)2Virtue Base ,-S (=O)2Heteroaryl ,-S (=O)2Naphthenic base ,-S (=O)2Heterocycle, aryl alkyl, heteroaryl alkyl, naphthenic base Alkyl or heterocyclylalkyl group；Wherein each X is selected from R by 1,2,3,4,5,6,7,8,9 or 10 individually optionally1aSubstituent group taken Generation；
RaAnd RbIt is each independently alkyl, alkenyl, alkynyl ,-C (=O)-alkyl ,-C (=O)-alkenyl ,-C (=O)-alkynes Base ,-C (=O)-O- alkyl ,-C (=O)-O- alkenyl or-C (=O)-O- alkynyl；
Each R1And R1aIt independently is fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxyl, alkyl, halogenated alkyl, alkane Oxygroup, halogenated alkoxy, alkylamino, halogenated alkylamino, alkylthio group, halogenated alkylthio ,-C (=O)-alkyl ,-C (=O)-alkene Base ,-C (=O)-alkynyl ,-S (=O)2Alkyl ,-S (=O)2Alkenyl or-S (=O)2Alkynyl；
A and T is each independently aryl, heteroaryl, naphthenic base, cycloalkenyl or heterocycle；Wherein A and T respectively independently appoints Selection of land is selected from R by 1,2,3,4,5,6,7,8,9 or 102Substituent group replaced；
Each R2It independently is fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxyl, alkyl, halogenated alkyl, alcoxyl Base, halogenated alkoxy, alkylamino, halogenated alkylamino, alkylthio group or halogenated alkylthio；
Wherein X, Ra、Rb、R1And R2R is respectively selected from by one or more individually optionally3Substituent group replaced；
Each R3It independently is hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, nitro, amino, carboxyl, C1-6Alkyl, C2-6Alkenyl, C2-6Alkynyl, halogenated C1-6Alkyl, halogenated C2-6Alkenyl, halogenated C2-6The C that alkynyl, hydroxyl replace1-6The C that alkyl, amino replace1-6Alkane The C that base, cyano replace1-6Alkyl, C1-6Alkoxy, halogenated C1-6The C that alkoxy, hydroxyl replace1-6Alkoxy, amino replace C1-6The C that alkoxy, cyano replace1-6Alkoxy, C1-6Alkylamino, C3-8Naphthenic base, C6-10Aryl or C1-9Heteroaryl.
In some of embodiments, Y1、Y2、Y3And Y4It is each independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyanogen Base, hydroxyl, carboxyl, C1-10Alkyl, C2-8Alkenyl, C2-8Alkynyl, C1-10Alkoxy, C2-8Alkenyloxy group, C2-8Alkynyloxy group, C6-10Aryl, C1-9Heteroaryl, C3-12Naphthenic base, C2-12Heterocycle, C6-10Aryl C1-6Alkyl, C1-9Heteroaryl C1-6Alkyl, C3-12Naphthenic base C1-6 Alkyl, C2-12Heterocycle C1-6Alkyl ,-C (=O)-C1-10Alkyl ,-C (=O)-C2-8Alkenyl ,-C (=O)-C2-8Alkynyl ,-C (= O)-C6-10Aryl ,-C (=O)-C1-9Heteroaryl ,-C (=O)-C3-12Naphthenic base ,-C (=O)-C2-12Heterocycle ,-C (=O)-O- C1-8Alkyl ,-C (=O)-O-C2-8Alkenyl ,-C (=O)-O-C2-8Alkynyl ,-C (=O)-C1-6Alkylidene-C6-10Aryl ,-C (= O)-C2-6Alkenylene-C6-10Aryl ,-C (=O)-C1-6Alkylidene-C1-9Heteroaryl ,-C (=O)-C2-6Alkenylene-C1-9Heteroaryl Base ,-C (=O)-C1-6Alkylidene-C3-8Naphthenic base ,-C (=O)-C2-6Alkenylene-C3-8Naphthenic base ,-C (=O)-C1-6Alkylidene- C2-10Heterocycle ,-C (=O)-C2-6Alkenylene-C2-10Heterocycle ,-S (=O)2-C1-6Alkyl ,-S (=O)2-C2-6Alkenyl ,-S (=O)2-C2-6Alkynyl ,-S (=O)2-C6-10Aryl ,-S (=O)2-C1-9Heteroaryl ,-S (=O)2-C3-8Naphthenic base ,-S (=O)2- C2-10Heterocycle ,-OX or-NRaRb；Wherein Y1、Y2、Y3And Y4Respectively individually optionally by 1,2,3,4,5,6,7,8,9 or 10 Selected from R1Substituent group replaced；
Wherein X, Ra、RbAnd R1With meaning as described in the present invention.
In some of embodiments, each X independently is hydrogen, C1-8Alkyl, C2-8Alkenyl, C2-8Alkynyl ,-C (=O)-C1-10 Alkyl ,-C (=O)-C2-8Alkenyl ,-C (=O)-C2-8Alkynyl ,-C (=O)-C6-10Aryl ,-C (=O)-C1-9Heteroaryl ,-C (= O)-C3-12Naphthenic base ,-C (=O)-C2-12Heterocycle ,-C (=O)-O-C1-10Alkyl ,-C (=O)-O-C2-8Alkenyl ,-C (=O)- O-C2-8Alkynyl ,-S (=O)2-C1-10Alkyl ,-S (=O)2-C2-8Alkenyl ,-S (=O)2-C2-8Alkynyl ,-S (=O)2-C6-10Virtue Base ,-S (=O)2-C1-9Heteroaryl ,-S (=O)2-C3-12Naphthenic base ,-S (=O)2-C2-12Heterocycle, C6-10Aryl C1-6Alkyl, C1-9Heteroaryl C1-6Alkyl, C3-12Naphthenic base C1-6Alkyl or C2-12Heterocycle C1-6Alkyl；Wherein each X individually optionally by 1,2, 3,4,5,6,7,8,9 or 10 are selected from R1aSubstituent group replaced；
Wherein R1aWith meaning as described in the present invention.
In some of embodiments, RaAnd RbIt is each independently C1-6Alkyl, C2-6Alkenyl, C2-6Alkynyl ,-C (=O)- C1-6Alkyl ,-C (=O)-C2-6Alkenyl ,-C (=O)-C2-6Alkynyl ,-C (=O)-O-C1-6Alkyl ,-C (=O)-O-C2-6Alkenyl Or-C (=O)-O-C2-6Alkynyl.
In some of embodiments, each R1And R1aIt independently is fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxylic Base, C1-6Alkyl, halogenated C1-6Alkyl, C1-6Alkoxy, halogenated C1-6Alkoxy, C1-6Alkylamino, halogenated C1-6Alkylamino, C1-6Alkane Sulfenyl, halogenated C1-6Alkylthio group ,-C (=O)-C1-6Alkyl ,-C (=O)-C2-6Alkenyl ,-C (=O)-C2-6Alkynyl ,-S (=O)2- C1-6Alkyl ,-S (=O)2-C2-6Alkenyl or-S (=O)2-C2-6Alkynyl.
In some of embodiments, A and T are each independently C6-10Aryl, C1-9Heteroaryl, C3-8Naphthenic base, C3-8Ring Alkenyl or C2-10Heterocycle；Wherein A and T is selected from R by 1,2,3,4,5,6,7,8,9 or 10 respectively individually optionally2Substituent group It is replaced；
Wherein R2With meaning as described in the present invention.
In some of embodiments, each R2Independently be fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxyl, C1-6Alkyl, halogenated C1-6Alkyl, C1-6Alkoxy, halogenated C1-6Alkoxy, C1-6Alkylamino, halogenated C1-6Alkylamino, C1-6Alkylthio group Or halogenated C1-6Alkylthio group.
In some of embodiments, Y1、Y2、Y3And Y4It is each independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyanogen Base, hydroxyl, carboxyl, C1-8Alkyl, C2-6Alkenyl, C2-6Alkynyl, C1-6Alkoxy, C2-4Alkenyloxy group, C2-4Alkynyloxy group, C6-10Aryl, C1-5Heteroaryl, C3-6Naphthenic base, C3-8Heterocycle, C6-10Aryl C1-3Alkyl, C1-9Heteroaryl C1-3Alkyl, C3-6Naphthenic base C1-3Alkane Base, C3-8Heterocycle C1-3Alkyl ,-C (=O)-C1-8Alkyl ,-C (=O)-C2-6Alkenyl ,-C (=O)-C2-6Alkynyl ,-C (=O)- C6-10Aryl ,-C (=O)-C1-9Heteroaryl ,-C (=O)-C3-10Naphthenic base ,-C (=O)-C3-8Heterocycle ,-C (=O)-O-C1-6 Alkyl ,-C (=O)-O-C2-6Alkenyl ,-C (=O)-O-C2-6Alkynyl ,-C (=O)-C1-4Alkylidene-C6-10Aryl ,-C (=O)- C2-4Alkenylene-C6-10Aryl ,-C (=O)-C1-4Alkylidene-C1-5Heteroaryl ,-C (=O)-C2-4Alkenylene-C1-5Heteroaryl ,-C (=O)-C1-4Alkylidene-C3-6Naphthenic base ,-C (=O)-C2-4Alkenylene-C3-6Naphthenic base ,-C (=O)-C1-4Alkylidene-C2-6It is miscellaneous Ring group ,-C (=O)-C2-4Alkenylene-C2-6Heterocycle ,-S (=O)2-C1-4Alkyl ,-S (=O)2-C2-4Alkenyl ,-S (=O)2- C2-4Alkynyl ,-S (=O)2-C6-10Aryl ,-S (=O)2-C1-5Heteroaryl ,-S (=O)2-C3-6Naphthenic base ,-S (=O)2-C2-6It is miscellaneous Ring group ,-OX or-NRaRb；Wherein Y1、Y2、Y3And Y4Respectively R is selected from by 1,2,3,4,5,6,7,8,9 or 10 individually optionally1 Substituent group replaced；
Wherein X, Ra、RbAnd R1With meaning as described in the present invention.
In some of embodiments, each X independently is hydrogen, C1-6Alkyl, C2-6Alkenyl, C2-6Alkynyl ,-C (=O)-C1-6 Alkyl ,-C (=O)-C2-6Alkenyl ,-C (=O)-C2-6Alkynyl ,-C (=O)-C6-10Aryl ,-C (=O)-C1-5Heteroaryl ,-C (= O)-C3-6Naphthenic base ,-C (=O)-C3-8Heterocycle ,-C (=O)-O-C1-4Alkyl ,-C (=O)-O-C2-4Alkenyl ,-C (=O)-O- C2-4Alkynyl ,-S (=O)2-C1-4Alkyl ,-S (=O)2-C2-4Alkenyl ,-S (=O)2-C2-4Alkynyl ,-S (=O)2-C6-10Aryl ,-S (=O)2-C1-9Heteroaryl ,-S (=O)2-C3-6Naphthenic base ,-S (=O)2-C3-8Heterocycle, C6-10Aryl C1-3Alkyl, C1-5Heteroaryl Base C1-3Alkyl, C3-6Naphthenic base C1-3Alkyl or C3-8Heterocycle C1-3Alkyl；Wherein each X individually optionally by 1,2,3,4,5,6, 7,8,9 or 10 are selected from R1aSubstituent group replaced；
Wherein R1aWith meaning as described in the present invention.
In some of embodiments, RaAnd RbIt is each independently C1-4Alkyl, C2-4Alkenyl, C2-4Alkynyl ,-C (=O)- C1-4Alkyl ,-C (=O)-C2-4Alkenyl ,-C (=O)-C2-4Alkynyl ,-C (=O)-O-C1-4Alkyl ,-C (=O)-O-C2-4Alkenyl Or-C (=O)-O-C2-4Alkynyl.
In some of embodiments, each R1And R1aIt independently is fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxylic Base, C1-4Alkyl, halogenated C1-4Alkyl, C1-4Alkoxy, halogenated C1-4Alkoxy, C1-4Alkylamino, halogenated C1-4Alkylamino, C1-4Alkane Sulfenyl, halogenated C1-4Alkylthio group ,-C (=O)-C1-4Alkyl ,-C (=O)-C2-4Alkenyl ,-C (=O)-C2-4Alkynyl ,-S (=O)2- C1-4Alkyl ,-S (=O)2-C2-4Alkenyl or-S (=O)2-C2-4Alkynyl.
In other embodiment, Y1、Y2、Y3And Y4It is each independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyanogen Base, hydroxyl, carboxyl ,-OCH3、-OCH2CH3、-OCH2CH2CH3、-OCH(CH3)2、-OCH2CH(CH3)2、-OC(CH3)3、- OCH2CH2CH2CH2CH3、-OCH2CH2CH(CH3)2、-OCH2CH(CH3)CH2CH3、-OCH(CH2CH3)2、-OC(CH3)2CH2CH3、- OCH2CH2CH2CH2CH2CH3,-OCH=CH2、-OCH2CH=CH2、-OCH2CH2CH=CH2、-OCH2CH=CHCH3、- OCH2CH2CH2CH=CH2、-OCH2CH2CH=CHCH3、-OC≡CH、-OCH2-C≡CH、-OCH2-C≡CCH3、-OCH2CH2-C ≡CH、-OCH2-C≡CCH2CH3,-OX or-N (Boc)2；Wherein Y1、Y2、Y3And Y4Respectively individually optionally by by 1,2,3,4,5 Or 6 be selected from R1Substituent group replaced；
Wherein R1With meaning as described in the present invention.
In other embodiment, each X independently is hydrogen ,-CH3、-CH2CH3、-CH2CH2CH3、-CH(CH3)2、- CH2CH(CH3)2、-C(CH3)3、-CH2CH2CH2CH2CH3、-CH2CH2CH(CH3)2、-CH2CH(CH3)CH2CH3、-CH (CH2CH3)2、-C(CH3)2CH2CH3、-CH2CH2CH2CH2CH2CH3,-CH=CH2、-CH2CH=CH2、-CH2CH2CH=CH2、- CH2CH=CHCH3、-C≡CH、-CH2-C≡CH、-CH2-C≡CCH3,-C (=O)-CH3,-C (=O)-CH2CH3,-C (=O)- CH2CH2CH3,-C (=O)-CH (CH3)2,-C (=O)-CH2CH(CH3)2,-C (=O)-C (CH3)3,-C (=O)- CH2CH2CH2CH2CH3,-C (=O)-CH2CH2CH(CH3)2,-C (=O)-CH2CH(CH3)CH2CH3,-C (=O)-CH (CH2CH3)2,-C (=O)-C (CH3)2CH2CH3,-C (=O)-CH2CH2CH2CH2CH2CH3,-C (=O)-CH2CH2CH2CH (CH3)2,-C (=O)-CH=CH2,-C (=O)-CH2CH=CH2,-C (=O)-C ≡ CH ,-C (=O)-CH2- C ≡ CH ,-C (= O)-O-CH3,-C (=O)-O-CH2CH3,-C (=O)-O-CH2CH2CH3Or-C (=O)-O-CH (CH3)2；
Or each X independently is following subformula:
Wherein each X is selected from R by 1,2,3,4,5,6,7,8,9 or 10 individually optionally1aSubstituent group replaced；
Wherein R1aWith meaning as described in the present invention.
In other embodiment, each R1And R1aIt independently is fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxylic Base, methyl, ethyl, n-propyl, isopropyl, normal-butyl, tert-butyl, trifluoromethyl, methoxyl group, ethyoxyl, positive propoxy, isopropyl Oxygroup ,-NHCH3、-N(CH3)2、-NHCH2CH3、-SCH3、-SCH2CH3、-SCF3Or-SCH2CF3。
In some of embodiments, A and T are each independently C6-10Aryl, C1-9Heteroaryl, C3-6Naphthenic base, C3-6Ring Alkenyl or C2-8Heterocycle；Wherein A and T is selected from R by 1,2,3,4,5,6,7,8,9 or 10 respectively individually optionally2Substituent group It is replaced；
Wherein R2With meaning as described in the present invention.
In some of embodiments, each R2Independently be fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxyl, C1-4Alkyl, halogenated C1-4Alkyl, C1-4Alkoxy, halogenated C1-4Alkoxy, C1-4Alkylamino, halogenated C1-4Alkylamino, C1-4Alkylthio group Or halogenated C1-4Alkylthio group.
In other embodiment, A is following subformula:
In other embodiment, T is following subformula:
In some of embodiments, the present invention relates to a kind of compounds, for such as formula (Ia) compound represented or formula (Ia) salt of compound shown in, N- oxide, metal complex, metal complexes or (E) and (Z) isomers and they Mixture:
Wherein X, Y1、Y2And Y4With meaning as described in the present invention.
In some of embodiments, the present invention relates to a kind of compounds, for such as formula (Ib) compound represented or formula (Ib) salt of compound shown in, N- oxide, metal complex, metal complexes or (E) and (Z) isomers and they Mixture:
Wherein X, Y1、Y2And Y4With meaning as described in the present invention.
In some of embodiments, the present invention relates to a kind of compounds, for such as formula (II) compound represented or formula (II) salt of compound shown in, N- oxide, metal complex, metal complexes or (E) and (Z) isomers and they Mixture:
Wherein X has meaning as described in the present invention.
In some of embodiments, the present invention relates to a kind of compounds, for such as formula (IIa) compound represented or formula (IIa) salt of compound shown in, N- oxide, metal complex, metal complexes or (E) and (Z) isomers and they Mixture:
Wherein X has meaning as described in the present invention.
In some of embodiments, the present invention provides a kind of compound, is the compound with one of following structure Or salt, N- oxide, metal complex, metal complexes or (E) and (Z) isomery with one of following structural compounds Body and their mixture:
On the other hand, the present invention provides a kind of composition, includes compound of the present invention.
Some of embodiments are that it is living that composition of the present invention further includes acceptable surface in Pesticide Science Property agent and carrier.
On the other hand, the present invention provides compound of the present invention or composition of the present invention in control of plant disease Application.
Some of embodiments are that compound of the present invention or composition of the present invention are therapeutic or preventative Control the application in the plant pathogenic fungi of plant or crop.
Other embodiment is that compound of the present invention or composition of the present invention are in prevention and treatment cucumber downy mildew Application in bacterium or/and botrytis cinerea pers.
On the other hand, the present invention provides the side of the plant pathogenic fungi of the therapeutic or preventive control plant of one kind or crop Compound of the present invention or composition of the present invention are administered to seed, plant or fruit or are administered to just by method In the soil for growing or needing growing plant.
Formula (I) compound represented may be deposited with different stereoisomer or optical isomer or tautomeric form ?.The present invention includes the mixture and isotope form example of all such isomers and tautomer and its various ratios Such as deuterated compound.
It is worth noting that, the stereochemical structure of oxime part present in oximido-terazole derivatives of the present invention include (E) or (Z) isomers, and these stereoisomers constitute a part of the invention.
In the presence of the compound of the present invention can be in the form of tautomer, in where applicable, institute above and below It states compound and is interpreted as also including corresponding tautomeric form, even if these tautomeric forms are not bright in each case Really refer to.
The structure that the general formula that there is the compound of isotope enrichment the present invention to provide is described, in addition to one or more atom quilts It is replaced with selected atomic weight or the atom of mass number.The Exemplary isotopes that can be introduced into the compounds of this invention include hydrogen, Carbon, nitrogen, oxygen, phosphorus, sulphur, fluorine and chlorine isotope, such as2H,3H,11C,13C,14C,15N,17O,18O,18F,31P,32P,35S,36Cl With125I。
Any asymmetric atom (for example, carbon etc.) of disclosed compound of present invention can be enriched with racemic or enantiomer Form exist, such as (R)-, (S)-or (R, S)-configuration exist.
Content noted earlier only outlines certain aspects of the invention, but be not limited to these aspect and it is otherwise in Appearance will make more specific complete description below.
Detailed description of the invention
Definition and general terms
It will now be described in more detail certain embodiments of the present invention, the example is by the structural formula and chemical formula explanation that are appended.This Invention is intended to cover all replacement, modification and equivalent technical solutions, they are included in the present invention defined such as claim In range.Those skilled in the art will appreciate that many can be used in similar or equivalent method and material of the present invention The practice present invention.The present invention is not limited to method of the present invention and material.In document, patent and the similar material combined One or more or contradict in the case where (including but not limited to defined in term, term application, institutes different from the application Technology of description, etc.), it is subject to the application.
It will further be appreciated that certain features of the invention, be it is clearly visible, carry out in a number of independent embodiments Description, but can also provide in combination in a single embodiment.Conversely, various features of the invention, for brevity, It is described in a single embodiment, but can also be individually or with the offer of any suitable sub-portfolio.
Unless otherwise stated, all scientific and technical terminologies used in the present invention have with those skilled in the art of the invention's It is generally understood identical meaning.All patents of the present invention and public publication are integrally incorporated this hair by reference It is bright.
Unless otherwise stated, following definition used in the present invention should be applied.For purposes of the present invention, chemical element With the periodic table of elements CAS editions, and " Handbook of Chemistry and Physics ", the 75th edition, 1994 is consistent.In addition, organic chemistry General Principle can With reference to " Organic Chemistry ", Thomas Sorrell, University Science Books, Sausalito: 1999, and " March's Advanced Organic Chemistry " by Michael B.Smith and Jerry Description in March, John Wiley&Sons, New York:2007, entire contents are incorporated by reference into the present invention.
There is apparent conflict unless otherwise indicated or in context, the article " one " used herein, " one (kind) " " described " is intended to include "at least one" or " one or more ".Therefore, these articles used herein refer to one or The article of more than one (i.e. at least one) object.For example, " component " refers to one or more components, it is possible to have more than one Component be taken into account in the embodiment of the embodiment and use or use.
Term "comprising" is open language, that is, includes content specified by the present invention, but be not precluded otherwise Content.
" stereoisomer " refers to identical chemical constitution, but the spatially different change of arrangement mode of atom or group Close object.Stereoisomer includes enantiomter, diastereoisomer, conformer (rotational isomer), geometric isomer (cis/trans) isomers, atropisomer, etc..
" enantiomter " refers to two isomers that cannot be overlapped but be mutually mirror of a compound.
" diastereoisomer " refer to there are two or multiple chiral centres and its molecule not alloisomerism of mirror image each other Body.Diastereoisomer has different physical properties, such as fusing point, boiling point, spectral property and reactivity.Diastereoisomer is mixed Such as electrophoresis and chromatography, such as HPLC can be operated by high resolution analysis to separate by closing object.
Stereochemical definitions used in the present invention and rule generally follow S.P.Parker, Ed., McGraw-Hill Dictionary of Chemical Terms(1984)McGraw-Hill Book Company,New York；and Eliel,E.and Wilen,S.,“Stereochemistry of Organic Compounds”,John Wiley&Sons, Inc., New York, Stereochemical definitions described in 1994 and rule.
Many organic compounds exist with optical active forms, i.e., they, which have, rotates the plane of linearly polarized light Ability.When describing optically active compound, indicate molecule about one or more hand using prefix D and L or R and S The absolute configuration at property center.Prefix d and l or (+) and (-) are the symbols for the rotation of linearly polarized light caused by appointed compound, Wherein (-) or l indicate that compound is left-handed.Prefix is (+) or the compound of d is dextrorotation.A kind of specific alloisomerism Body is enantiomter, and the mixture of this isomers is referred to as enantiomeric mixture.The 50:50 mixture of enantiomter Referred to as racemic mixture or racemic modification, when chemical reaction or in the process without stereoselectivity or stereospecificity when, It may occur in which such case.
As described in the invention, the compound of the present invention can be optionally replaced one or more substituent groups, such as General formula compound above, or as example special inside embodiment, subclass, and a kind of compound that the present invention is included. It should be appreciated that this term can be used interchangeably " optionally replacing " this term with " substituted or non-substituted ".In general, art " substituted " the one or more hydrogen atoms indicated in given structure of language are replaced specific substituent group.Unless other aspect tables Bright, an optional substituent group can be replaced at various substitutable position of that group.When in given structural formula not Only a position can be replaced one or more substituent groups selected from specific group, then substituent group can identical or differently Replace at various locations.Wherein the substituent group can be, but be not limited to, deuterium, fluorine, chlorine, bromine, iodine, cyano, hydroxyl, nitre Base, amino, carboxyl, alkyl, alkoxy, alkoxyalkyl, alkyloxy-alkoxy, alkoxy alkylamino, aryloxy group, heteroaryl oxygen Base, heterocycle oxygroup, alkoxy aryl, heteroarylalkoxy, heterocyclylalkoxy, cycloalkyl alkoxy, alkylamino, alkylamino Alkyl, alkylamino alkylamino, cycloalkyl amino, amino-n-cycloalkyl, alkylthio group, halogenated alkyl, halogenated alkoxy, hydroxyl replace Alkyl, hydroxyl replace alkylamino, cyano replace alkyl, cyano replace alkoxy, cyano replace alkylamino, amino Substituted alkyl, alkyl acyl, miscellaneous alkyl, naphthenic base, cycloalkenyl, cycloalkyl-alkyl, heterocycle, heterocyclylalkyl group, heterocycle Acyl group, aryl, aryl alkyl, fragrant amino, heteroaryl, heteroaryl alkyl, heteroaryl amino, amide groups, sulfonyl, aminosulfonyl Base etc..
In addition, it is necessary to explanation, unless otherwise explicitly point out, in the present invention used by describing mode " each ... independently be " and " ... be each independently " and " ... independently be " can be interchanged, and shall be understood in a broad sense, both may be used To refer among the different groups, does not influence mutually, can also indicate in phase between expressed specific option between the same symbol In same group, do not influenced mutually between expressed specific option between the same symbol.
It is disclosed in the substituent group of each section of this specification, disclosed compound of present invention according to radical species or range.It is special It does not point out, the present invention includes each independent sub-combinations thereof of each member of these radical species and range.For example, term “C1-C6Alkyl " or " C1-6Alkyl " refers in particular to the methyl being individually disclosed, ethyl, C3Alkyl, C4Alkyl, C5Alkyl and C6Alkyl.
Terminology used in the present invention " alkyl " or " alkyl group ", indicate contain 1 to 20 carbon atom, the straight chain of saturation or Branch univalent hydrocarbyl group；Replaced the substituent group that wherein alkyl group is optionally described by one or more present invention. Unless otherwise detailed instructions, alkyl group contains 1-20 carbon atom.In one embodiment, alkyl group contains 1-12 carbon Atom；In one embodiment, alkyl group contains 1-8 carbon atom；In another embodiment, alkyl group contains 1-6 A carbon atom；In yet another embodiment, alkyl group contains 1-4 carbon atom；Also in one embodiment, alkyl group contains There is 1-3 carbon atom.
The example of alkyl group includes, but is not limited to, methyl (Me ,-CH3), ethyl (Et ,-CH2CH3), n-propyl (n- Pr、-CH2CH2CH3), isopropyl (i-Pr ,-CH (CH3)2), normal-butyl (n-Bu ,-CH2CH2CH2CH3), isobutyl group (i-Bu ,- CH2CH(CH3)2), sec-butyl (s-Bu ,-CH (CH3)CH2CH3), tert-butyl (t-Bu ,-C (CH3)3), n-pentyl (- CH2CH2CH2CH2CH3), 2- amyl (- CH (CH3)CH2CH2CH3), 3- amyl (- CH (CH2CH3)2), 2- methyl -2- butyl (- C (CH3)2CH2CH3), 3- methyl -2- butyl (- CH (CH3)CH(CH3)2), 3- methyl-1-butyl (- CH2CH2CH(CH3)2), 2- first Base -1- butyl (- CH2CH(CH3)CH2CH3), n-hexyl (- CH2CH2CH2CH2CH2CH3), 2- hexyl (- CH (CH3) CH2CH2CH2CH3), 3- hexyl (- CH (CH2CH3)(CH2CH2CH3)), 2- methyl -2- amyl (- C (CH3)2CH2CH2CH3), 3- first Base -2- amyl (- CH (CH3)CH(CH3)CH2CH3), 4- methyl -2- amyl (- CH (CH3)CH2CH(CH3)2), 3- methyl -3- penta Base (- C (CH3)(CH2CH3)2), 2- methyl -3- amyl (- CH (CH2CH3)CH(CH3)2), 2,3- dimethyl -2- butyl (- C (CH3)2CH(CH3)2), 3,3- dimethyl -2- butyl (- CH (CH3)C(CH3)3), etc..
Term " alkylidene " expression removes the two of two obtained saturations of hydrogen atom from the linear chain or branched chain hydrocarbon of saturation Valency alkyl group.Unless otherwise detailed instructions, alkylidene group contains 1-12 carbon atom.In one embodiment, alkylidene Group contains 1-8 carbon atom；In one embodiment, alkylidene group contains 1-6 carbon atom；In another embodiment In, alkylidene group contains 1-4 carbon atom；In yet another embodiment, alkylidene group contains 1-3 carbon atom；Also exist In one embodiment, alkylidene group contains 1-2 carbon atom.Such example includes methylene (- CH2), ethylidene (- CH2CH2), propylidene (- CH2CH2CH2) ,-CH (CH3)CH2,-C (CH3)2,-CH2CH2CH(CH3)-,-CH2CH2C (CH3)2, etc..
Term " alkenyl " indicates the linear chain or branched chain monovalent hydrocarbon containing 2-12 carbon atom, wherein at least one insatiable hunger And site, that is, there is a carbon-to-carbon sp2Double bond, wherein the alkenyl group can be retouched optionally by one or more present invention Replaced the substituent group stated comprising the positioning of " cis " and " tans ", or the positioning of " E " and " Z ".In one embodiment, Alkenyl group includes 2-8 carbon atom；In another embodiment, alkenyl group includes 2-6 carbon atom；In another embodiment party In case, alkenyl group includes 2-4 carbon atom.The example of alkenyl group includes, but is not limited to, vinyl (- CH=CH2), Allyl (- CH2CH=CH2), acrylic (CH3- CH=CH-), the cyclobutenyl (CH of oxo3- C (=O)-CH=CH-) etc..
The obtained divalent alkylene base base of two hydrogen atoms is removed in term " alkenylene " expression from linear chain or branched chain alkene Group.Unless otherwise detailed instructions, alkenylene group contains 1-12 carbon atom.In one embodiment, alkenylene group contains 1-8 carbon atom；In one embodiment, alkenylene group contains 1-6 carbon atom；In another embodiment, alkenylene Group contains 1-4 carbon atom；In yet another embodiment, alkenylene group contains 1-3 carbon atom；Also in an embodiment In, alkenylene group contains 1-2 carbon atom.Such example includes-CH=CH- ,-CH=CH-CH2,-CH=CH-CH (CH3)-,-CH=CH-C (CH3)2, etc..
Term " alkynyl " indicates the linear chain or branched chain monovalent hydrocarbon containing 2-12 carbon atom, wherein at least one carbon- Tri- key of carbon sp.In one embodiment, alkynyl group includes 2-8 carbon atom；In another embodiment, alkynyl group includes 2-6 carbon atom；In yet another embodiment, alkynyl group includes 2-4 carbon atom.The example of alkynyl group includes, but simultaneously It is not limited to ,-C ≡ CH ,-CH2-C≡CH、-CH2-C≡CCH3、-CH2CH2-C≡CH、-CH2-C≡CCH2CH3Etc..
Term " alkoxy " indicates that alkyl group is connected by oxygen atom with molecule rest part, and wherein alkyl group has Meaning as described in the present invention.The example of alkoxy base includes, but is not limited to, methoxyl group (MeO ,-OCH3), ethyoxyl (EtO、-OCH2CH3), 1- propoxyl group (n-PrO, n- propoxyl group ,-OCH2CH2CH3), 2- propoxyl group (i-PrO, i- propoxyl group ,- OCH(CH3)2) etc..
Term " alkyl amino " or " alkylamino " include " N- alkyl amino " and " N, N- dialkyl amido ", wherein amino base Group is separately replaced one or two alkyl group.Some of embodiments are that alkyl amino is one or two C1-6Alkyl is connected to the alkylamino group of the lower level on nitrogen-atoms.Other embodiment is that alkyl amino is C1-3's The alkylamino group of lower level.Suitable alkylamino group can be alkyl monosubstituted amino or dialkyl amido, such reality Example includes, but is not limited to, N- methylamino, N- ethylamino, N, N- dimethylamino, N, N- lignocaine etc..
Term " alkylthio group " refers to that the alkyl of linear chain or branched chain is connected on the sulphur atom of divalent, and wherein alkyl group has such as Meaning of the present invention.The example of alkylthio radicals includes, but is not limited to ,-SCH3、-SCH2CH3、-SCH2CH2CH3Deng Deng.
Term " halogen " refers to fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).
Term " halogenated alkyl " indicates alkyl group replaced one or more halogen atoms, and such example includes, But it is not limited to ,-CF3,-CHF2,-CH2Cl ,-CH2CF3,-CH2CHF2,-CH2CH2CF3Deng.
Term " halogenated alkoxy " expression alkoxy base is replaced one or more halogen atoms, such example packet Contain, but is not limited to ,-OCF3,-OCHF2,-OCHCl2,-OCH2CHF2,-OCH2CHCl2,-OCH (CH3)CHF2Deng.
Term " halogenated alkylamino " indicates alkylamino radicals replaced one or more halogen atoms.
Term " halogenated alkylthio " indicates alkylthio radicals replaced one or more halogen atoms.
Term " naphthenic base " indicates containing 3-12 carbon atom, monovalent or multivalence saturation monocyclic, bicyclic or tricyclic body System.In one embodiment, naphthenic base includes 3-10 carbon atom；In another embodiment, naphthenic base includes that 3-8 carbon is former Son；In yet another embodiment, naphthenic base includes 3-6 carbon atom.The group of naphthene base is optionally by one or more sheets It invents replaced described substituent group.Such example includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopenta, hexamethylene Base, suberyl, cyclooctyl, cyclononyl, cyclodecyl, ring undecyl, cyclo-dodecyl, etc.；Or naphthenic base includes, but simultaneously It is not limited to having structure:
Term " cycloalkenyl " indicates containing 3-12 carbon atom, monovalent or multivalence monocyclic, bicyclic or tricyclic system, until It less include a carbon-carbon double bond, the ring system is nonaromatic.In one embodiment, cycloalkenyl includes that 3-10 carbon is former Son；In another embodiment, cycloalkenyl includes 3-8 carbon atom；In yet another embodiment, cycloalkenyl includes 3-6 carbon Atom.The cycloalkenyl groups are optionally replaced one or more substituent groups described in the invention.Such example packet It includes, but is not limited to, cyclobutane base, cyclopentenyl, cyclohexenyl group, cyclohexadienyl etc..
Term " heterocycle " and " heterocycle " are used interchangeably here, all refer to the saturation comprising 3-15 annular atom or portion Divide unsaturated monocyclic, bicyclic or tricyclic, does not include aromatic rings, and at least one annular atom in monocyclic, bicyclic or tricyclic wherein Selected from nitrogen, sulphur and oxygen atom.Unless otherwise stated, heterocycle can be carbon-based or nitrogen base, and-CH2Group can be optionally It is substituted by-C (=O)-.The sulphur atom of ring can optionally be oxidized to S- oxide.The nitrogen-atoms of ring can be optionally by oxygen It is melted into N- oxygen compound.The example of heterocycle includes, but are not limited to Oxyranyle, azelidinyl, oxetanylmethoxy, sulphur Heterocycle butyl, pyrrolidinyl (such as 2- pyrrolidinyl), 2- pyrrolinyl, 3- pyrrolinyl, pyrazolidinyl, imidazolinyl, imidazoles Alkyl, tetrahydrofuran base, dihydrofuryl, tetrahydro-thienyl, dihydrothiophene, 1,3- dioxy cyclopenta, two sulphur cyclopenta, four Hydrogen pyranose, dihydro pyranyl, 2H- pyranose, 4H- pyranose, tetrahydro thiapyran base, piperidyl (2- piperidyl, 3- piperidyl, 4- piperidyl), morpholinyl, thio-morpholinyl, (1- oxo)-thio-morpholinyl, (1,1- dioxo)-thio-morpholinyl, piperazine Base, dioxanes base, dithianyl, thiophene oxane base, high piperazine base, homopiperidinyl, oxepane alkyl, thia cycloheptyl alkyl, 2- Oxa- -5- azabicyclo [2.2.1] hept- 5- base, tetrahydro pyridyl.- CH in heterocycle2The reality that group is replaced by-C (=O)- Example includes, but are not limited to 2- oxo-pyrrolidine base, oxo -1,3-thiazoles alkyl, 2- piperidone base, 3,5- dioxy piperazine piperidinyls. The example that sulphur atom is oxidized in heterocycle includes, but are not limited to sulfolane base, 1,1- dioxothiomorpholinyl.It is described miscellaneous Cyclic groups are optionally replaced one or more substituent groups described in the invention.
In one embodiment, heterocycle includes 2-12 carbon atom and at least one is selected from the miscellaneous of nitrogen, sulphur and oxygen atom Atom；In one embodiment, heterocycle includes 2-10 carbon atom and at least one is selected from the miscellaneous original of nitrogen, sulphur and oxygen atom Son；In one embodiment, heterocycle includes 2-8 carbon atom and at least one is selected from the hetero atom of nitrogen, sulphur and oxygen atom；? In one embodiment, heterocycle includes 2-6 carbon atom and at least one is selected from the hetero atom of nitrogen, sulphur and oxygen atom；It is real one It applies in scheme, heterocycle includes 2-4 carbon atom and at least one is selected from the hetero atom of nitrogen, sulphur and oxygen atom；In an embodiment party In case, heterocycle includes 3-12 carbon atom and at least one is selected from the hetero atom of nitrogen, sulphur and oxygen atom；In an embodiment In, heterocycle includes 3-10 carbon atom and at least one is selected from the hetero atom of nitrogen, sulphur and oxygen atom；In one embodiment, Heterocycle includes 3-8 carbon atom and at least one is selected from the hetero atom of nitrogen, sulphur and oxygen atom；In one embodiment, heterocycle Base includes 3-6 carbon atom and at least one is selected from the hetero atom of nitrogen, sulphur and oxygen atom；In one embodiment, heterocycle packet Containing 2-5 carbon atom and at least one hetero atom selected from nitrogen, sulphur and oxygen atom.
Contain one or more degrees of unsaturation in " unsaturated " the expression group of term as used in the present invention.
Term " hetero atom " refers to O, S, N, P and Si, the form including any oxidation state of N, S and P；Primary, secondary, tertiary amine and season The form of ammonium salt；Or the substituted form of hydrogen in heterocycle on nitrogen-atoms, for example, N is (as in 3,4- dihydro-2 h-pyrrole base N), NH (as the NH in pyrrolidinyl) or NR (NR in pyrrolidinyl replaced as N-).
Term " aryl " indicates the monocycle containing 6-14 annular atom or 6-12 annular atom or 6-10 annular atom, double The carbocyclic ring system of ring and tricyclic, wherein at least one ring system be it is aromatic, wherein each ring system include 3-7 original Molecular ring, and there are one or more attachment points to be connected with the rest part of molecule.Term " aryl " can be with term " fragrance Ring " is used interchangeably.The example of aryl group may include phenyl, indenyl, naphthalene and anthryl.The aryl group is optionally by one Replaced a or multiple substituent groups described in the invention.
Monocycle of term " heteroaryl " expression containing 5-12 annular atom or 5-10 annular atom or 5-6 annular atom, Bicyclic and three-ring system, wherein at least one ring system are aromatic, and at least one ring system includes one or more miscellaneous Atom, wherein each ring system includes 5-7 former molecular ring, and has one or more attachment points and molecule rest part It is connected.Term " heteroaryl " can be used interchangeably with term " hetero-aromatic ring " or " heteroaromatics ".The heteroaryl groups are appointed Selection of land is replaced one or more substituent groups described in the invention.In one embodiment, 5-10 original is molecular miscellaneous Aryl includes 1,2,3 or 4 hetero atom for being independently selected from O, S and N.
In one embodiment, heteroaryl basis representation contains 1-9 carbon atom and at least one is selected from nitrogen, sulphur and oxygen atom Hetero atom；In one embodiment, heteroaryl basis representation contains 1-6 carbon atom and at least one is selected from nitrogen, sulphur and oxygen atom Hetero atom；In one embodiment, heteroaryl basis representation contains 1-5 carbon atom and at least one is selected from nitrogen, sulphur and oxygen atom Hetero atom；In one embodiment, heteroaryl basis representation contains 1-4 carbon atom and at least one is selected from nitrogen, sulphur and oxygen atom Hetero atom；In one embodiment, heteroaryl basis representation contains 2-4 carbon atom and at least one is selected from nitrogen, sulphur and oxygen atom Hetero atom.
The example of heteroaryl groups includes, but is not limited to, 2- furyl, 3- furyl, TMSIM N imidazole base, 2- imidazole radicals, 4- imidazole radicals, 5- imidazole radicals, 3- isoxazolyl, 4- isoxazolyl, 5- isoxazolyl, 2- oxazolyl, 4- oxazolyl, 5- oxazole Base, N- pyrrole radicals, 2- pyrrole radicals, 3- pyrrole radicals, 2- pyridyl group, 3- pyridyl group, 4- pyridyl group, 2- pyrimidine radicals, 4- pyrimidine radicals, 5- Pyrimidine radicals, pyridazinyl (such as 3- pyridazinyl), 2- thiazolyl, 4- thiazolyl, 5- thiazolyl, tetrazole radical (such as 5- tetrazole radical), triazole Base (such as 2- triazolyl and 5- triazolyl), 2- thienyl, 3- thienyl, pyrazolyl, isothiazolyl, 1,2,3-oxadiazoles base, 1, 2,5- oxadiazoles bases, 1,2,4- oxadiazoles base, 1,2,3-triazoles base, 1,2,3- thio biphosphole base, 1,3,4- thio biphosphole base, 1, 2,5- thio biphosphole bases, pyrazinyl, 1,3,5-triazines base, pyrimidine ketone group, pyriconyl；It also include below bicyclic, but never It is bicyclic to be limited to these: benzimidazolyl, benzofuranyl, benzo tetrahydrofuran base, benzothienyl, indyl (such as 2- indoles Base), etc..
In one embodiment, heteroaryl groups are following subformula:
Etc..
Term " aryl alkyl " refers to that alkyl is substituted with aryl, and is connected by alkyl group with the rest part of molecule；Its Middle alkyl and aryl group have meaning as described in the present invention.Term " heteroaryl alkyl " refers to that alkyl is substituted by heteroaryl, It is connected by alkyl group with the rest part of molecule；Wherein alkyl or heteroaryl groups have meaning as described in the present invention. Term " cycloalkyl-alkyl " refers to that alkyl is substituted by cycloalkyl, and is connected by alkyl group with the rest part of molecule；Wherein alkane Base or group of naphthene base have meaning as described in the present invention.Term " heterocyclylalkyl group " refers to that alkyl is replaced by heterocycle, leads to Alkyl group is crossed to be connected with the rest part of molecule；Wherein alkyl or heterocyclyl groups have meaning as described in the present invention.
As described herein, attachment point can be connected any attachable position on ring with molecule rest part；Such as formula a In have an attachment point that can be connected with molecule rest part, as shown in formula b, formula c and formula d.It is attached when ring is bicyclic or polycyclic Point can be connected with molecule rest part any attachable position on each ring；As there is an attachment point can be in formula e Molecule rest part is connected, as shown in formula f, formula g, formula h, formula i and formula j.
As described herein,It indicates that the compound comprising carbon-to-nitrogen double bon can be Z configuration, is also possible to E configuration, Or indicate the mixture of Z configuration and E configuration.
When the compound of the present invention includes an acid moieties, the salt of compound of the present invention, including derived from alkali gold Belong to or those of alkaline-earth metal and is derived from those of ammonia and amine.Preferred cation includes sodium, potassium, magnesium and has chemistry Formula N+(R19R20R21R22) ammonium cation, wherein R19、R20、R21And R22Independently selected from hydrogen, C1-C6Alkyl and C1-C6Hydroxyl alkane Base.The salt of compound with chemical formula (I) can by with metal hydroxides (such as sodium hydroxide) or amine (such as ammonia, Trimethylamine, diethanol amine, 2- methyl mercapto propylamine, diallyl amine, 2- butoxyethylamine, morpholine, ring lauryl amine or benzylamine) to tool There is the compound of chemical formula (I) to be handled to prepare.
When the compound of the present invention includes an alkali part, acceptable salt can be formed by organic acid and inorganic acid, Such as acetic acid, propionic acid, lactic acid, citric acid, tartaric acid, succinic acid, fumaric acid, maleic acid, malonic acid, mandelic acid, malic acid, neighbour Phthalic acid, hydrochloric acid, hydrobromic acid, phosphoric acid, nitric acid, sulfuric acid, methanesulfonic acid, naphthalene sulfonic acids, benzene sulfonic acid, toluenesulfonic acid, camphorsulfonic acid with And similarly known acceptable acid.
Composition and preparation of the compounds of this invention and application thereof
The present invention provides a kind of fungicide composite, the composition includes: a effective amount of logical as herein defined Formula (I) compound acceptable carrier (support), carrier or filler (filler) as active constituent and agriculturally.
According to the present invention, term " carrier " indicates a kind of natural or synthesis organic or inorganic compound, with formula (I) Active compound or joint so that reactive compound is easier to be applied to plant, especially to the part of plant. Therefore, this carrier is usually inert, and should be agriculturally acceptable.Carrier can be solid or liquid.Suitable load The example of body include clay, natural or synthetic silicate, silica, resin, wax, solid fertilizer, water, alcohols (especially Butanol), organic solvent, mineral oil and vegetable oil and its derivative.Also the mixture of such carrier can be used.
Composition of the invention can also include other components.Specifically, the composition also may include surfactant. The surfactant can be ionic or non-ionic emulsifier, dispersing agent or wetting agent or these surfactants Mixture.Such as, it may include polyacrylate, lignosulphonates, sulfocarbolate or naphthalene sulfonate, ethylene oxide and fatty alcohol or With fatty acid or with the condensation polymer of fatty amine, substituted phenol (especially alkyl phenol or aryl phenol), the salt of sulfosuccinate, ox Sulfonic acid (especially taurine Arrcostab), the phosphate of oxyethylated alcohol or phenol, polyalcohol aliphatic ester and The derivative of above compound comprising sulfate radical, sulfonate radical or phosphonate functional group.In general, when reactive compound and/or lazy When medium reagent that is that property carrier is insoluble in water and being applied is water, it is necessary to which there are at least one surfactants.Preferably, With the poidometer of composition, the content of surfactant is 5-40 weight %.
Optionally, may also include other components, for example, protective colloid, adhesive, thickener, thixotropic agent, bleeding agent, Stabilizer, chelating agent.It more generally, can be by the reactive compound and any solid or liquid that meet common preparation technique Additive is combined.
In general, composition of the invention may include the reactive compound of 0.05-99 weight %, preferably 10-70 weight %.
Composition of the invention can in a variety of manners using and can be used for various preparations, such as aerosol dispersing agent, glue Capsule suspending agent (capsule suspension), harl concentrating agents, can dusting powder, emulsifiable concentrating agents, oil-in-water emulsion, oil Packet aqueous emulsion, encapsulated granula, fine grained agent, the flowable concentrating agents for seed treatment, gas (under pressure) preparation, gas hair Raw agent, granule, hot mist concentrating agents, big granula, fine granule, oily dispersible powder, the flowable concentrating agents of oily compatibility, oil are mixed Insoluble liquid, paste, plant spillikin, the seed for doing kind of a pulvis for processing, coated pesticidal, soluble concentrating agents, solubility Pulvis, the solution for seed treatment, suspension concentrating agents (flowable concentrating agents), ultra-low volume (ULV) liquid, ultra-low volume (ULV) granula or tablet, water dispersible pulvis, water-soluble granule or tablet for slurries processing, use can be dispersed in suspending agent, water In the water solube powder and wettability pulvis of seed treatment.These compositions not only include that will use suitable equipment (example Such as sprayer or dusting equipment) it is applied to the composition on processed plant or seed, and be included in and be applied to crops The commercial composite for the concentration that must be diluted before.
Preparation can be prepared by mode known to script, such as by the way that active constituent and at least one is following conventional It is prepared by material mixing: expanding material, surfactant, solvent or diluent, adjuvant, emulsifier, dispersing agent and/or binder or Fixative, wetting agent, waterproofing agent, (if applicable) desiccant and UV stabilizer, and (if applicable) dyestuff With pigment, defoaming agent, preservative, inorganic and organic thickening agent, adhesive, gibberellin and other processing aids and water.According to Preparation type to be prepared needs other procedure of processings, such as wet grinding, dry grinding and granulation.
In solid pharmaceutical preparation, the vegetalitas such as soy meal, wheat flour powder, diatomite, apatite, gypsum, cunning can be used Organic and inorganic compounds such as the minerals such as stone, bentonite, pyrophillite, clay micropowder, sodium benzoate, urea, sodium sulphate etc. Additive and/or carrier.
In liquid preparation, can be used the petroleum distillates such as kerosene, dimethylbenzene and solvent naphtha, hexamethylene, cyclohexanone, Dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloro ethylene, methyl iso-butyl ketone (MIBK), mineral oil, vegetable oil, water equal solvent.
It is a further object of the invention to provide a kind of method of control plant, the plant pathogenic fungi of crop or seed, It is characterized in that, by agriculturally effectively and substantially non-phytotoxic amount microbicide compositions of the invention with seed treatment, Leaf portion applies, stem applies, be impregnated with or the mode of trickle irrigation application (chemistry applies) is applied to following part: seed, plant or plant Object fruit, or planted or intended the soil or inert base (such as inorganic matrix, such as sand, asbestos, mineral wool of planting plants； Expand minerals, such as perlite, vermiculite, zeolite or expanded clay), float stone, pyroclast substance or material, synthesis it is organic Matrix (such as polyurethane), organic substrate (such as peat, compost, trees waste product (such as coconut husk, wood-fibred or sawdust, tree Skin)) or fluid matrix (such as floating hydroponic system, nutrient film techinique, gas carrying agent system).
The amount of application of fungicide of the present invention according to meteorological condition, dosage form, Dressing date, method of administration, application place, Control object disease, object crop etc. are different and different, but usually every 1 hectare of effective component chemical combination object amount is 0.01~1000g, excellent It is selected as 10~100g.
Term administering is in plant to be processed " it is understood to refer to for purposes of the present invention, it can be by following various Processing method applies the composition pesticide as present subject matter:
One, liquid of the aerial part spraying comprising one of the composition of Xiang Suoshu plant；
Two, it dusts in the surrounding plants, particle or powder is incorporated into soil, is spraying and when the plant is It is injected or is smeared in the case where trees；
Three, by the plant protection mixture comprising one of the composition, to the seed of the plant carry out coating or Film coating.
Method of the invention can be healing, prevention or the method eradicated.
It is such as but not limited to the crop of composition pesticide or combined treatment of the invention, such as vine, can also be Cereal, vegetables, clover, soybean, commercially available garden crop, turf, trees or gardening plant.
Processing method of the invention can also be used to handling propagation material (such as stem tuber or rhizome) and seed, seedling or Transplant seedling and plant or transplanting plant.The processing method can also be used for processing root.Processing method of the invention can also be used for Handle the aerial part of plant, such as the trunk in relation to plant, stem or stalk, leaf, flower and fruit.
Can with or can have cotton, flax, liana, fruit or vegetables with the plant that method of the invention is protected Crop, as (for example, pip fruit, such as apple and pears, there are also drupe, such as apricot, almond for rosaceae (Rosaceae sp.) (almond) and peach), tea sugarcane scarabaeidae (Ribesioidae sp.), Juglandaceae (Juglandaceae sp.), Betulaceae (Betulaceae sp.), Anacardiaceae (Anacardiaceae sp.), Fagaceae (Fagaceae sp.), Moraceae (Moraceae sp.), Oleaceae (Oleaceae sp.), Actinidiaceae (Actinidaceaesp.), Lauraceae (Lauraceae Sp.), Musaceae (Musaceae sp.) (such as Banana tree and powder bajiao banana (plantins)), Rubiaceae (Rubiaceae Sp.), Theaceae (Theaceae sp.), Sterculiaceae (Sterculiceae sp.), Rutaceae (Rutaceae sp.) (such as Lemon, orange and grape fruit)；Solanaceae (Solanaceae sp.) (such as tomato), Liliaceae (Liliaceae sp.) are purple Aster section (Asteraceae sp.) (such as lettuce), Umbelliferae (Umbelliferae sp.), Cruciferae (Cruciferae Sp.), Chenopodiaceae (Chenopodiaceae sp.), Curcurbitaceae (Cucurbitaceae sp.), Papilionaceae (Papilionaceae sp.) (such as pea), rosaceae (Rosaceae sp.) (such as strawberry)；Chief crop, such as grass Section (Graminae sp.) (such as corn, lawn or cereal such as wheat, rice, barley and triticale), aster section (Asteraceae Sp.) (such as sunflower), crucifer (such as rape), pulse family (Fabacae sp.) (such as peanut), Papilionaceae (Papilionaceae sp.) (such as soybean), Solanaceae (Solanaceae sp.) (such as potato), Chenopodiaceae (Chenopodiaceae sp.) (such as beet root)；Garden crop and forestry crop；And the genetic changec of these crops Homologue.
In the disease of controllable plant or crop by the method for the invention, it can be mentioned that:
Powdery mildew, such as:
Powdery mildew (Blumeria diseases) is caused by such as wheat powdery mildew (Blumeria graminis)；
Podosphaera disease (Podosphaera diseases), by for example white cross hair list softgel shell (Podosphaera Leuco-tricha) cause；
Sphaerotheca disease (Sphaerotheca diseases), by such as Siberian cocklebur monofilament shell (Sphaerotheca Fuliginea caused by)；
Uncinula disease (Uncinula diseases), such as caused by grape fishing line shell (Uncinula necator)；
Rust, such as:
Glue Rust is sick (Gymnosporangium diseases), by such as absorption unit rest fungus (Gymnosporangium Sabinae) cause；
Hunchbacked spore rust (Hemileia diseases), is drawn by such as coffee rust (Hemileia vastatrix) It rises；
Phakopsora disease (Phakopsora diseases), by such as Phakopsora pachyrhizi (Phakopsora Pachyrhizi) or mountain horseleech layer rest fungus (Phakopsora meibomiae) causes；
Puccinia disease (Puccinia diseases), such as drawn by Puccinia recondita (Puccinia recondite) It rises；
Uromyces disease (Uromyces diseases), by such as wart top uromyce (Uromyces Appendiculatus) cause；
Oomycetes disease (Oomycete diseases), such as:
Bremia disease (Bremia diseases) is obstructed mould (Bremia lactucae) by such as lettuce disk and is caused；
Peronospora disease (Peronospora diseases), by such as pea downy mildew (Peronospora pisi) or rape Downy mildew (P.brassicae) causes；
Phytophthora disease (Phytophthora diseases), by such as phytophthora infestans (Phytophthora Infestans) cause；
Plasmopara disease (Plasmopara diseases), by the raw uniaxial mould (Plasmopara of such as grape Viticola) cause；
Pseudoperonospora disease (Pseudoperonospora diseases), by such as humulus grass downy mildew Caused by (Pseudoperonospora humuli) or cucumber downy mildew (Pseudoperonospora cubensis)；
Pythium disease (Pythium diseases), is caused by such as Pythium ultimum (Pythium ultimum)；
Leaf spot, leaf blotch and leaf blight, such as:
Alternaria disease (Alternaria diseases), such as drawn by alternaria solani sorauer (Alternaria solani) It rises；
Cercospora disease (Cercospora diseases), it is raw tail spore (Cercospora beticola) by such as beet Cause；
Chrysosporium disease (Cladiosporum diseases), such as by melon fruit fly (Cladiosporium Cucumerinum) cause；
Cochliobolus disease (Cochliobolus diseases), such as by standing grain cochliobolus (Cochliobolus Sativus) cause；
Colletotrichum disease (Colletotrichum diseases) pierces disk spore (Colletotrichum by such as beans Lindemuthianum) cause；
Olive peacock's eye disease disease (Cycloconium diseases), by such as olive peacock plaque (Cycloconium oleaginum) causes；
Beancurd sheet shell bacterium layer is sick (Diaporthe diseases), is drawn by seat shell between such as citrus (Diaporthe citri) It rises；
Elsinoe disease (Elsinoe diseases), by such as citrus Elsinochrome (Elsinoe fawcettii) Cause；
Long spore belongs to sick (Gloeosporium diseases), by for example happy long spore (Gloeosporium of colour disk Laeticolor) cause；
Small cluster shell belongs to sick (Glomerella diseases), by such as GLOMERFLLA CINGULATA (Glomerella cingulate) Cause；
Ball seat Pseudomonas is sick (Guignardia diseases), by such as grape Guignardia (Guignardia Bidwellii) cause；
Leptosphaeria disease (Leptosphaeria diseases), by such as Cruciferae ball cavity bacteria (Leptosphaeria maculans), the withered ball cavity bacteria (Leptosphaeria nodorum) of grain husk cause；
Rice blast (Magnaporthe diseases) is caused by such as rice blast fungus (Magnaporthe grisea)；
Mycosphaerella disease (Mycosphaerella diseases), by such as standing grain green-ball chamber bacterium (Mycosphaerella Graminicola), peanut spherical cavity bacterium (Mycosphaerella arachidicola), banana secret note tikka bacterium Caused by (Mycosphaerella fijiensis)；
Septoria disease (Phaeosphaeria diseases), by such as phaeosphaeria nodorum (Phaeosphaeria Nodorum) cause；
Pyrenophora disease (Pyrenophora diseases), such as drawn by circle nuclear cavity bacteria (Pyrenophora teres) It rises；
Ramularia disease (Ramularia diseases), by for example pungent strutting every spore (Ramularia collo- Cygni) cause；
Beak genuss disease (Rhynchosporium diseases), by such as rye beak spore (Rhynchosporium Secalis) cause；
Septoria disease (Septoria diseases), by such as Septoria apii (Septoria apii) or tomato Septoria musiva (Septoria lycopersici) causes；
Core coral bacterium is sick (Typhula diseases), is caused by for example yellowish pink core coral bacterium (Typhula incarnata)；
Venturia disease (Venturia diseases), such as drawn by venturia inaequalis (Venturia inaequalis) It rises；
Root disease and stem disease, such as:
Photovoltaicing leather bacteria disease (Corticium diseases), is drawn by such as standing grain photovoltaicing leather bacteria (Corticium graminearum) It rises；
(mould) category of Fusariumsp is sick (Fusarium diseases), is drawn by for example sharp fusarium (Fusarium oxysporum) It rises；
Sturgeon shape belongs to sick (Gaeumannomyces diseases), by such as gaeumannomyce (Gaeumannomyces Graminis) cause；
Rhizoctonia disease (Rhizoctonia diseases), by such as Rhizoctonia solani Kuhn (Rhizoctonia solani) Cause；
Ta Pusi (Tapesia diseases), by such as Ta Pusi clostruidium (Tapesia acuformis) Cause；
Thiclaviopsis disease (Thielaviopsis diseases), by such as thielaviopsis sp (Thielaviopsis Basicola) cause；
Ear fringe and panicle disease, such as:
Alternaria disease (Alternaria diseases), is caused by such as rod method (Alternaria spp.)；
Aspergillosis (Aspergillus diseases) is caused by such as aspergillus flavus (Aspergillus flavus)；
Branch spore is sick (Cladosporium diseases), is caused by such as branch spore (Cladosporium spp.)；
Claviceps disease (Claviceps diseases), is caused by such as ergot (Claviceps purpurea)；
(mould) category of Fusariumsp is sick (Fusarium diseases), is drawn by such as machete fusarium (Fusarium culmorum) It rises；
Head blight (Gibberella diseases) is caused by such as Gibberella zeae (Gibberella zeae)；
Rice Gerlachia oryaae (Monographella diseases), by such as rice cloud shape bacterium (Monographella Nivalis) cause；
Smut and bunt, such as:
Axis Ustilago is sick (Sphacelotheca diseases), by such as silk axis smut (Sphacelotheca Reilinana) cause；
Tilletia disease (Tilletia diseases), by such as Tilletia caries (Tilletia caries) Cause；
Urocystis disease (Urocystis diseases), by such as hidden smut (Urocystis occulta) Cause；
Ustilago disease (Ustilago diseases), is caused by such as naked smut (Ustilago nuda)；
Fruit rot and mycosis, such as:
Aspergillosis (Aspergillus diseases) is caused by such as aspergillus flavus (Aspergillus flavus)；
Botrytis belongs to sick (Botrytis diseases), is caused by such as botrytis (Botrytis cinerea) 's；
Penicilliosis (Penicillium diseases) is drawn by such as sweet potato mould (Penicillium expansum) It rises；
Sclerotinia disease (Sclerotinia diseases), by such as sclerotinite (Sclerotinia Sclerotiorum) cause；
Verticillium disease (Verticilium diseases), by such as black and white wheel branch spore (Verticillium Alboatrum) cause；
Rotten, mouldy, withered, corrupt and samping off in seed and soil:
Alternariosis (Alternaria diseases), by such as mustard rod method (Alternaria brassicicola) Cause；
Aphanomyces disease (Aphanomyces diseases), by such as mould (Aphanomyces of pea silk capsule Euteiches) cause；
Ascochyta disease (Ascochyta diseases), is drawn by such as two born of the same parents bacterium of crystalline lens (Ascochyta lentis) It rises；
Aspergillosis (Aspergillus diseases) is caused by such as aspergillus flavus (Aspergillus flavus)；
Branch spore is sick (Cladosporium diseases), is drawn by such as multi-trunk natalensis (Cladosporium herbarum) It rises；
Cochliobolus disease (Cochliobolus diseases), such as by standing grain cochliobolus (Cochliobolus Sativus) (Conidiaform:Drechslera, Bipolaris Syn:Helminthosporium) causes；
It is sick (Colletotrichum diseases) to pierce disk spore, disk spore (Colletotrichum is pierced by such as coccoid Coccodes) cause；
(mould) category of Fusariumsp is sick (Fusarium diseases), is drawn by such as machete fusarium (Fusarium culmorum) It rises；
Head blight (Gibberella diseases) is caused by such as Gibberella zeae (Gibberella zeae)；
Shell ball spore is sick (Macrophomina diseases), by such as beans shell ball spore (Macrophomina Phaseolina) cause；
Rice Gerlachia oryaae (Monographella diseases), by such as rice cloud shape bacterium (Monographella Nivalis) cause；
Penicilliosis (Penicillium diseases) is drawn by such as sweet potato mould (Penicillium expansum) It rises；
Phoma sp disease (Phoma diseases), is caused by such as balck shank (Phoma lingam)；
Fungi point mold (Phomopsis diseases) is caused by such as soybean Phoma sp (Phomopsis sojae)；
Phytophthora disease (Phytophthora diseases), is drawn by such as Phytophthora cactorum (Phytophthora cactorum) It rises；
Nuclear cavity bacteria disease (Pyrenophora diseases), by such as wheat nuclear cavity bacteria (Pyrenophora graminea) Cause；
Pyricularia Sacc. disease (Pyricularia diseases), is caused by such as Magnaporthe grisea (Pyricularia oryzae) 's；
Pythium disease (Pythium diseases), is caused by such as Pythium ultimum (Pythium ultimum)；
Rhizoctonia disease (Rhizoctonia diseases), by such as Rhizoctonia solani Kuhn (Rhizoctonia solani) Cause；
Head mold disease (Rhizopus diseases) is caused by such as Rhizopus oryzae (Rhizopus oryzae)；
Pyrenomycetes disease (Sclerotium diseases), is drawn by such as Sclerotium rolfsii (Sclerotium rolfsii) It rises；
Septoria musiva disease (Septoria diseases), such as caused by phaeosphaeria nodorum (Septoria nodorum)；
Core coral bacterium is sick (Typhula diseases), is caused by for example yellowish pink core coral bacterium (Typhula incarnata)；
It is sick (Verticillium diseases) to take turns branch spore, by such as Verticilliumdahliae (Verticillium Dahliae) cause；
Ulcer, cracking and top dry, such as:
Nectria disease (Nectria diseases), is drawn by for example dry red shell bacterium of cancer clump (Nectria galligena) It rises；
Wilt disease, such as:
Chain sclerotinia sclerotiorum belong disease (Monilinia diseases), is drawn by such as drupe chain sclerotinia sclerotiorum (Monilinia laxa) It rises；
Leaf bubble or leaf curl, such as:
Exoascus disease (Taphrina diseases) is drawn by for example lopsided external capsule bacterium (Taphrina deformans) It rises；
Wood plant decline disease, such as:
It is sick (Esca diseases) according to section, drawn by such as head mold lattice spore bacterium (Phaeomoniella clamydospora) It rises；
Eutypa dieback (Eutypa dyeback) is caused by such as grapevine da mping-off fungi (Eutypa lata)；
Dutch elm disease (Dutch elm disease), is caused by such as silique category mite (Ceratocystsc ulmi)；
Colored and seed disease, such as:
Botrytis belongs to sick (Botrytis diseases), is caused by such as botrytis (Botrytis cinerea) 's；
Tubers disease, such as:
Rhizoctonia disease (Rhizoctonia diseases), by such as Rhizoctonia solani Kuhn (Rhizoctonia solani) Cause；
Helminthosporium disease (Helminthosporium diseases), by for example founding the compacted spore of withered length (Helminthosporium solani) causes.
The compound of the present invention can also be with one or more insecticides, fungicide, bactericide, attractant, acaricide Or pheromonal activity substance or other biologically active compounds mix.Thus obtained mixture has broad spectrum of activity. It is particularly advantageous with the mixture of other Fungicidal compounds.The mixture of compound comprising formula (I) and bactericidal compound It is also particularly advantageous with composition of the invention.
The example for the fungicide that can be suitably mixed is selected from following: benzimidazole methyl carbamate class is antifungal The compound of agent, the compound of dicarboximide class fungicide, demethylation inhibin class fungicide compound, benzamide Compound, the amine/morpholine of class fungicide kill the change of the compound of class epiphyte pharmaceutical, phosphatide biosynthesis inhibin class fungicide Close object, the compound of carboxyl acylamide fungicide, the compound of hydroxyl (2- amino -) pyrimidine fungicide, aniline pyrimidine class The compound of fungicide, the compound of N- carbanilate class fungicide, inhibin class fungicide outside quinone Compound, the compound of phenylpyrrole class fungicide, the compound of quinolines fungicide, lipid peroxidized inhibin class are killed The compound of epiphyte pharmaceutical, melanocyte biosynthesis inhibin-reduction enzyme fungicide compound, melanocyte biosynthesis inhibit Element-the compound of dehydration enzyme fungicide, the compound of hydroxy benzenes amine fungicide, squalene-epoxidase inhibin class The compound of fungicide, the compound of polyoxin class fungicide, the compound of phenyl ureas fungicide, the suppression of quinone inside Compound, the enol pyrans uronic acid antibiotics of the compound, benzamides fungicide of making plain class fungicide kill very The compound of microbial inoculum, the compound of own pyrans sugar-antibiotics fungicide, glucopyranosyl antibiotic: protein synthesizes class Compound, the glucopyranosyl antibiotic of fungicide: the compound of trehalase and inose biosynthesis class fungicide, The compound of cyanoacetamide oximes fungicide, the compound of Carbamates fungicide, oxidative phosphorylation uncoupling The compound of class fungicide, the compound of organic tin fungicide, the compound of carboxylic acids fungicide, the heteroaryl same clan kill The compound of epiphyte pharmaceutical, the compound of phosphonic acid ester fungicide, the compound of phthalamidic acid class fungicide, phentriazine class are killed The compound of epiphyte pharmaceutical, the compound of benzene sulfonamide fungicide, pyridazinone fungicide compound, thiophenecarboxamides The compound of class fungicide, the compound of pyrimidine amides fungicide, carboxyl acylamide fungicide compound, tetracycline The compound of antibiotics fungicide, the compound of thiocarbamates fungicide, benzamides fungicide Compound, the host plant defence compound of induction type fungicide, multidigit point contact activity class fungicide compound And the compound of other fungicides.
Further, the example of fungicide compound is selected from following: benomyl, carbendazim, thiophanate-methyl, corruption are mould Benefit, iprodione, vinclozolin, epoxiconazole, Fluquinconazole, Triadimenol, simeconazoles, kind bacterium azoles, triforine, cyproconazole, Difenoconazole, Flusilazole, Flutriafol, metconazole, nitrile bacterium azoles, prochloraz, propiconazole, prothioconazoles, Tebuconazole, fluorine ether azoles, Metalaxyl-M, first White spirit, mefenoxam, M 9834, benalaxyl-M, furalaxyl, ofurace, Wakil, cartap, dodemorph, butylbenzene Morpholine, tridemorph, Trimorfamid Fademorf, fenpropidin, pipron, volution bacterium amine, edifenphos, Isoprothiolane, Boscalid, pyrrole thiophene bacterium Amine, bixafen, carboxin, oxycarboxin, ethirimol, cyprodinil, diethofencarb, Fluoxastrobin, pyraclostrobin, gram glad, oxime of receipts Bacterium ester, ZEN 90160, pyribencarb, Famoxate, Fenamidone, discostrobin, enestrobin, dimoxystrobin, benzene Oxygen bacterium amine, orysastrobin, fluoxastrobin, fenpiclonil, fludioxonil, fast promise sweet smell, chloroneb, pyroquilon, tricyclazole, cyclopropyl acyl bacterium Amine, fenhexamid, pyributicarb, polyoxin, Pencycuron, match seat go out, amisulbrom, oxamides, blasticidin S-S, spring thunder Mycin, streptomysin, jinggangmeisu, cymoxanil, Propamocarb, prothiocarb, iodo propinyl butyl carbamate, fluazinam, pleasure are killed Mite, ferimzone, dinocap, dinocap, fentin acetate, oxolinic acid, hymexazol, phosphorous acid and its various salt, triethylphosphine acid Aluminium, tecloftalam, azoles bacterium piperazine, flusulfamide, diclomezine, Silthiopham, difluoro woods, dimethomorph, benzene metsulfovax, benzene metsulfovax-are different Propyl, Propineb, downy mildew go out, mandipropamid, flumorph, oxytetracycline, methasulfocarb, fluopicolide, fluopyram, I Acid benzene-S-methyl, Cupravit, copper sulphate, Kocide SD, Bordeaux mixture composition (ternary copper sulphate), elementary sulfur, maneb Zinc, Carbatene, Propineb, fervam, maneb, arasan, zineb, ziram, folpet, captan, enemy Bacterium pellet, Bravo, Guardian, cyflufenamid, the third oxygen quinoline, metrafenone, the chloro- 6- of 5- (2,4,6- trifluorophenyl) -7- (4- first Phenylpiperidines -1- base) [1,2,4] triazol [1,5-a] pyrimidine, the iodo- 3- propyl -4H-1- benzopyran-4-one of 2- butoxy -6-, 3- [5- (4- chlorphenyl) -2,3- dimethyl -3- isoxazolidinyl] pyridine, N- [1- [[[1- (4- cyano-phenyl) ethyl] sulphonyl Base] methyl] propyl] carbamic acid 4- fluorobenzene ester, N- [[(cyclo propyl methoxy) amino] [6- (difluoro-methoxy) -2,3- difluoro Phenyl] methylene] phenyl acetamide, N '-[4- [4- chloro- 3- (trifluoromethyl) phenoxy group] -2,5- 3,5-dimethylphenyl]-N- ethyl - N- methyl carboximidamide, 2- [[2- fluoro- 5- (trifluoromethyl) phenyl] sulfenyl] -2- [3- (2- methoxyphenyl) Asia -2- thiazole Alkyl] acetonitrile and N- (the chloro- 2- nitrobenzophenone of 4-)-N- ethyl -4- methyl benzenesulfonamide.
The example for the bactericide that can be suitably mixed can be selected from following: bronopol, double fluorine phenol, N-Serve, dimethyl Aminodithioformic acid nickel, kasugarnycin, octhilinone, furancarboxylic acid, terramycin, probenazole, streptomysin, tecloftalam, copper sulphate With other copper agents.
General synthesis process
In the present specification, if there are any difference between chemical name and chemical structure, structure is dominant.Generally Ground, the compound of the present invention described method can be prepared through the invention, unless there are further instruction.Following Synthetic schemes and embodiment 1-39 are for being further illustrated the contents of the present invention.
Synthetic schemes one
Target compound 1 can be prepared by synthetic schemes one, and wherein halo indicates that halogen, X have such as institute of the present invention The meaning stated.It reacts the compound of embodiment 1 and X-halo to obtain target compound 1.
Embodiment
Embodiment 1 (Z)-(1- methyl-1 H- tetrazolium -5- base) (phenyl) ketone O- ((7- chlorobenzene simultaneously [d] isoxazole -3- base) Methyl) oxime
The synthesis of step 1, intermediate 2- hydroxyl -3- chloro-acetophenone
2- chlorophenol (19.2g, 150.0mmol) is added in the three neck round bottom of 500.0mL, is added dropwise at 0 DEG C Chloroacetic chloride (12.9g, 165.0mmol) after completion of dropwise addition, is stirred at room temperature 2 hours.130 DEG C are then heated to, by anhydrous three Aluminium chloride (35.9g, 270.0mmol) is added in round-bottomed flask, is stirred 2 hours.After reaction, water quenching is carefully added dropwise to go out instead It answers, ethyl acetate extraction, after washing, saturated common salt washing and anhydrous sodium sulfate drying, is concentrated to give crude product.
The synthesis of step 2, intermediate (E) -1- (3- chlorine-2-hydroxyl phenyl) acetophenone oxime
2- hydroxyl -3- chloro-acetophenone (23.0g, 135.0mmol) and hydroxylamine hydrochloride (18.6g, 270.0mmol) are dissolved in first In alcohol (200.0mL), sodium acetate (25.5g, 311.0mmol) is then added.It is heated to reflux 12 hours, after reaction, Filtering, concentration are added water dissolution, then are extracted with ethyl acetate, and collect organic solvent through washing, saturated common salt washing and anhydrous sulphur Sour sodium is dry, is concentrated to get crude product.
The synthesis of the chloro- 3- methyl benzo isoxazole of step 3, intermediate 7-
By (E) -1- (3- chlorine-2-hydroxyl phenyl) acetophenone oxime (22.0g, 119.0mmol), anhydrous sodium acetate (22.0g, It 274.0mmol) is dissolved in DMF (100.0mL), flows back 12 hours with acetic anhydride (85.0g, 833.0mmol), after reaction, A certain amount of ice water is added into reaction solution, ethyl acetate extraction is dry through washing, saturated common salt washing and anhydrous sodium sulfate Afterwards, concentration, column chromatography (petrol ether/ethyl acetate (v/v)=10/1), obtain product (4.0g).
The synthesis of step 4, intermediate 3- (bromomethyl) -7- chloro-benzisoxazole
By the chloro- 3- methyl benzo isoxazole (4.0g, 24.0mmol) of 7-, NBS (12.8g, 72.0mmol) and AIBN (1.6g, 9.6mmol) is dissolved in carbon tetrachloride (100mL), is flowed back 12 hours, after reaction, is filtered, concentration, column chromatography (petrol ether/ethyl acetate (v/v)=10/1), obtains product (1.8g).
Step 5, ((7- chlorobenzene is simultaneously [d] different by (phenyl) ketone O- for target compound (Z)-(1- methyl-1 H- tetrazolium -5- base) Oxazole -3- base) methyl) oxime synthesis
At room temperature, 3- (bromomethyl) -7- chloro-benzisoxazole (247.0mg, 1.0mmol) is dissolved in DMF (10.0mL), Sequentially add potassium carbonate (276.0mg, 2.0mmol) and (Z)-(1- methyl-1 H- tetrazolium -5- base) (phenyl) ketoxime (162.0mg, 0.8mmol) after being stirred overnight, water quenching reaction, ethyl acetate extraction, through water are carefully added dropwise into reaction solution It washes, after saturated common salt washing and anhydrous sodium sulfate drying, concentration, column chromatography (petrol ether/ethyl acetate (v/v)=3/1) obtain white Color solid (150.0mg, 41%).
1H NMR(400MHz,CDCl3):δ7.58-7.53(m,2H),7.50-7.44(m,3H),7.40-7.36(m,2H), 7.32-7.28(m,1H),5.66(s,2H),3.91(s,3H).
LC-MS:m/z 369.10[M+H]+.
The objective body compound of table 1 can be obtained using corresponding raw material by the similar synthetic method of embodiment 1.
Table 1
Embodiment 11 (Z)-(1- methyl-1 H- tetrazolium -5- base) (phenyl) ketone O- ((5- hydroxy benzo [d] isoxazole -3- Base) methyl) oxime
The synthesis of step 1, intermediate (E) -1- (2,5- dihydroxy phenyl) acetophenone oxime
By 2,5-dihydroxyacetophenone (15.2g, 100.0mmol), hydroxylamine hydrochloride (13.8g, 200.0mmol) and anhydrous second Sour sodium (18.9g, 230.0mmol) is substantially soluble in methanol (200.0mL), and flow back 2h, and reaction solution is filtered, and is concentrated, and use is water-soluble Solution, ethyl acetate extraction are concentrated to give crude product after washing, saturated common salt washing and anhydrous sodium sulfate drying.
The synthesis of step 2, intermediate 3- methyl benzo isoxazole -5- acetic acid esters
(E) -1- (2,5- dihydroxy phenyl) acetophenone oxime (9.6g, 57.5mmol) is dissolved in DMF (100.0mL).Then Add anhydrous sodium acetate (10.8g, 132.3mmol) and acetic anhydride (41.1g, 402.5mmol) reflux 12h.After reaction, Vacuum distillation removes acetic anhydride and DMF, and a certain amount of water is then added, and ethyl acetate extraction is concentrated, and dry, column chromatographs (petroleum Ether/ethyl acetate (v/v)=10/1), obtain product (6.0g, 55%).
The synthesis of step 3, intermediate 3- (bromomethyl) benzo isoxazole -5- acetic acid esters
At room temperature, 3- methyl benzo isoxazole -5- acetic acid esters (3.8g, 20.0mmol) is dissolved in CCl4In (50mL), according to Secondary addition NBS (10.7g, 60.0mmol) and AIBN (1.3g, 8.0mmol), flow back 12h, after reaction, filters, concentration, column It chromatographs (petrol ether/ethyl acetate (v/v)=10/1), obtains product (1.5g, 28%).
Step 4, intermediate (Z) -3- (((((1- methyl-1 H- tetrazolium -5- base) (phenyl) methylene) amino) oxygroup) first Base) benzo [d] isoxazole -5- yl acetate synthesis
By 3- methyl benzo isoxazole -5- acetic acid esters (4.0g, 15.0mmol) and (Z)-(1- methyl-1 H- tetrazolium -5- base) (phenyl) ketoxime (2.4g, 12.0mmol) is dissolved in DMF (40mL), then adds potassium carbonate (4.1g, 30.0mmol), 12h is stirred at room temperature, after reaction, water is added, and be extracted with ethyl acetate, through washing, saturated common salt washing and anhydrous sulphur After sour sodium is dry, concentration, column chromatography (petrol ether/ethyl acetate (v/v)=5/1) obtain product (3.5g, 57%).
Step 5, target compound (Z)-(1- methyl-1 H- tetrazolium -5- base) (phenyl) ketone O- ((5- hydroxy benzo [d] Isoxazole -3- base) methyl) oxime synthesis
By (Z) -3- (((((1- methyl-1 H- tetrazolium -5- base) (phenyl) methylene) amino) oxygroup) methyl) benzo [d] Isoxazole -5- yl acetate (5.9g, 15.0mmol) is dissolved in the mixed solution of tetrahydrofuran and water (tetrahydrofuran/water (v/ V)=1/1), sodium hydroxide (1.2g, 30.0mmol) then is added, is stirred overnight at room temperature, after reaction, be concentrated, be added Water dissolution, is extracted with ethyl acetate, dry, and concentration, column chromatography (petrol ether/ethyl acetate (v/v)=4/1) obtain white solid (1.5g, 29%).
1H NMR(400MHz,CDCl3):δ7.80(s,1H),7.50-7.45(m,4H),7.42-7.38(m,2H),7.17- 7.15 (m, 1H) 6.90 (d, J=2.4Hz, 1H) 6.26 (s, 1H) 5.65 (s, 2H), 3.95 (s, 3H)
LC-MS:m/z 350.54[M+H]+.
Embodiment 12 (Z) -3- (((((1- methyl-1 H- tetrazolium -5- base) (phenyl) methylene) amino) oxygroup) methyl) benzene And [d] isoxazole -5- base heptanoate
By (Z)-(1- methyl-1 H- tetrazolium -5- base) (phenyl) ketone O- ((5- hydroxy benzo [d] isoxazole -3- base) first Base) oxime (200.0mg, 0.6mmol) is dissolved in methylene chloride (20.0mL), be then added triethylamine (242.0mg, 2.4mmol) with DMAP (7.3mg, 0.06mmol), oenanthyl chloro (178.0mmol) then is added dropwise.It is stirred overnight, reacts at room temperature After, concentration, column chromatography (petrol ether/ethyl acetate (v/v)=10/3) obtain white solid (110mg, 41%).
The objective body compound of table 2 can be obtained using corresponding raw material by the similar synthetic method of embodiment 12.
Table 2
Biological Examples
This test case is used to measure the bactericidal activity of compound obtained in embodiment.Experiment target in this test case is designated as Botrytis cinerea pers and bacterium of downy mildew of cucumber.It is spare that 1%EC is dissolved into DMF.Using living body pot-culture method, these compounds are evaluated To 2 experiment target target bactericidal activities under 500mg/L dosage.Test method (is killed using initiative pesticide bioactivity evaluation SOP Microbial inoculum volume).
Bacterium of downy mildew of cucumber (Pseudoperonospora cubensis): 1 leaf period (plucking growing point) of selection is long The consistent potting cucumber seedling of gesture, naturally dry after spraying treatment, is inoculated with afterwards for 24 hours after processing, takes fresh cucumber downy mildew sick Leaf dips the lower sick leaf back sporangium of distillation washing with writing brush, is made into sporangia suspension (2-3 × 105/ml).With inoculation Sprayer (pressure 0.1MPa) even spraying on cucumber seedling is inoculated with, and the test material after inoculation moves to phjytotron, keeps opposite Humidity 100%, temperature are 21 DEG C or so, keep 21 DEG C of temperature or so afterwards for 24 hours, and 95% or so moisturizing of relative humidity induces, after 5d Classification investigation is carried out depending on blank control incidence, refers to calculating preventive effect by disease.
Botrytis cinerea pers (Botrytis cinerea): blade bacterination process is used.Select two leaf period growing ways consistent Potting cucumber seedling connects bacteria cake on blade after reagent spray dries.After 24-26 DEG C of half-light moisturizing for 24 hours, restore natural lighting Moisturizing culture about 3d.Each vaccination lesion diameter is measured with slide calliper rule after the onset of wait compare sufficiently, calculates preventive effect.
Test result
Embodiment 2, embodiment 3, embodiment 4, embodiment 13, embodiment 17, embodiment 25 and embodiment 34 are to cucumber cream Mildew preventive effect reaches 100%.
Embodiment 13, embodiment 14, embodiment 19, embodiment 25, embodiment 27, embodiment 32 and embodiment 33 are to cucumber The preventive effect of gray mold reaches 100%.
It is very good that the compounds of this invention has plant pathogenic fungi, especially bacterium of downy mildew of cucumber and botrytis cinerea pers Control efficiency；Better than oximido-tetrazole compound of commercially available fungicide and structure proximate.

Claims (5)

1. a kind of compound is the salt or (E) and (Z) isomery of the compound as shown in formula (II) compound represented or formula (II) Body and their mixture:
Wherein:
X is C2-4Alkenyl ,-C (=O)-phenyl ,-C (=O)-pyridyl group ,-C (=O)-thienyl ,-S (=O)2Phenyl ,-S (= O)2Pyridyl group or phenyl C1-3Alkyl-；X is selected from R by 1 or 2 individually optionally1aSubstituent group replaced；
Each R1aIt independently is fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxyl, C1-4Alkyl, halogenated C1-4Alkyl, C1-4 Alkoxy or halogenated C1-4Alkoxy.
2. compound according to claim 1, in which:
X is-CH=CH2；Or X is following subformula:
Wherein each X is selected from R by 1 or 2 individually optionally1aSubstituent group replaced；
Each R1aIt independently is fluorine, chlorine, bromine or iodine.
3. a kind of compound, be the compound with one of following structure or the salt with one of following structural compounds or (E) and (Z) isomers and their mixture:
4. a kind of composition, living comprising surface acceptable in compound described in claim 1-3 any one and Pesticide Science Property agent and carrier.
5. compound described in claim 1-3 any one or composition as claimed in claim 4 are in control of plant disease Application.
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