JPH04112872A - Plant phycomycete disease control agent containing isonicotinic acid derivative as active ingredient - Google Patents
Plant phycomycete disease control agent containing isonicotinic acid derivative as active ingredientInfo
- Publication number
- JPH04112872A JPH04112872A JP23049590A JP23049590A JPH04112872A JP H04112872 A JPH04112872 A JP H04112872A JP 23049590 A JP23049590 A JP 23049590A JP 23049590 A JP23049590 A JP 23049590A JP H04112872 A JPH04112872 A JP H04112872A
- Authority
- JP
- Japan
- Prior art keywords
- group
- agent
- active ingredient
- lower alkyl
- disease control
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 201000010099 disease Diseases 0.000 title claims abstract description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 25
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 24
- 239000004480 active ingredient Substances 0.000 title claims abstract description 9
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical class OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical class NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- -1 N-substituted pyrazolyl group Chemical group 0.000 claims description 21
- 241000233866 Fungi Species 0.000 claims description 12
- 241000195493 Cryptophyta Species 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 16
- 239000000843 powder Substances 0.000 abstract description 8
- 239000000839 emulsion Substances 0.000 abstract description 7
- 239000008187 granular material Substances 0.000 abstract description 5
- 239000002270 dispersing agent Substances 0.000 abstract description 3
- 239000003995 emulsifying agent Substances 0.000 abstract description 3
- 239000000080 wetting agent Substances 0.000 abstract description 3
- 239000003085 diluting agent Substances 0.000 abstract description 2
- 230000009969 flowable effect Effects 0.000 abstract description 2
- 241000233679 Peronosporaceae Species 0.000 abstract 1
- 238000013329 compounding Methods 0.000 abstract 1
- 239000002245 particle Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 5
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 241000233614 Phytophthora Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 241000233622 Phytophthora infestans Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 235000009754 Vitis X bourquina Nutrition 0.000 description 3
- 235000012333 Vitis X labruscana Nutrition 0.000 description 3
- 240000006365 Vitis vinifera Species 0.000 description 3
- 235000014787 Vitis vinifera Nutrition 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000233616 Phytophthora capsici Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241000219094 Vitaceae Species 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000008361 aminoacetonitriles Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 150000003851 azoles Chemical class 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 235000021021 grapes Nutrition 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
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- SLWCJTWQTBPPDJ-UHFFFAOYSA-N 2-amino-4-methylpent-3-enenitrile Chemical compound CC(C)=CC(N)C#N SLWCJTWQTBPPDJ-UHFFFAOYSA-N 0.000 description 1
- YHKLLTUNTUJQSB-UHFFFAOYSA-N 2-chloro-6-methylpyridine-4-carbonyl chloride Chemical compound CC1=CC(C(Cl)=O)=CC(Cl)=N1 YHKLLTUNTUJQSB-UHFFFAOYSA-N 0.000 description 1
- AJVPPRMYXQSRIB-UHFFFAOYSA-N 2-chloro-n-(cyanomethyl)pyridine-4-carboxamide Chemical compound ClC1=CC(C(=O)NCC#N)=CC=N1 AJVPPRMYXQSRIB-UHFFFAOYSA-N 0.000 description 1
- NPRZWOJTSGFSBF-UHFFFAOYSA-N 2-chloropyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC(Cl)=C1 NPRZWOJTSGFSBF-UHFFFAOYSA-N 0.000 description 1
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- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- 238000007059 Strecker synthesis reaction Methods 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
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- NQSJOBCWGOKIMH-UHFFFAOYSA-N n-(cyanomethyl)pyridine-4-carboxamide Chemical class N#CCNC(=O)C1=CC=NC=C1 NQSJOBCWGOKIMH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
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- OWKRYNJWNLBLNR-UHFFFAOYSA-N pent-3-ynenitrile Chemical compound CC#CCC#N OWKRYNJWNLBLNR-UHFFFAOYSA-N 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
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- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical class ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は一部新規な化合物を含むイソニコチン酸アミド
誘導体を有効成分として含有することを特徴とする藻菌
類による植物病害防除剤に関するものである。[Detailed Description of the Invention] [Field of Industrial Application] The present invention relates to an agent for controlling plant diseases caused by algae and fungi, which is characterized by containing as an active ingredient an isonicotinamide derivative containing a partially novel compound. be.
現在、藻菌類による植物病害に対してはキャブタン、キ
ャプタホル、ジチオカーバメート系殺菌剤、クロロタロ
ニルなどが広く用いられている。Currently, cabtane, captafol, dithiocarbamate fungicides, chlorothalonil, and the like are widely used to treat plant diseases caused by algal fungi.
しかし、これらの薬剤は予防効果か主であり、治療効果
かほとんとないことから、発病か認められてからの薬剤
処理による防除という場面には使用てきないという欠点
をもっている。However, these drugs have only a preventive effect and little therapeutic effect, so they have the disadvantage that they cannot be used for control by chemical treatment after the onset of the disease is recognized.
一方、その後開発されたアシルアラニン系殺菌剤、たと
えばメタラキシルは治療効果もあわせもっているか、既
にその薬剤耐性菌の出現により、防除効果か低下してき
ており問題となってきている。On the other hand, the acylalanine fungicides that have been developed since then, such as metalaxyl, have become a problem because their control effects have been reduced due to the appearance of drug-resistant bacteria, although they may also have therapeutic effects.
イソニコチン酸アミド誘導体に関しては、本出願人によ
り、特開昭６２−２６５２６２号公報、特開昭６３１３
０５８２号公報、特開昭６３−１３０５８３号公報にお
いて、イネいもち病、イネ白葉枯病、キュウリ斑点細菌
病に対して高い防除効果を示すことか開示されているか
、ぺと病や疫病なとの藻菌類による植物病害に対する防
除効果については全く報告されていない。Regarding isonicotinic acid amide derivatives, the present applicant has disclosed JP-A-62-265262 and JP-A-6313.
No. 0582 and Japanese Unexamined Patent Publication No. 63-130583 disclose whether it shows a high control effect on rice blast, rice bacterial leaf blight, and cucumber spot bacterial disease, or whether it shows high control effects on rice blast, rice leaf blight, and cucumber spot bacterial disease. There have been no reports on the control effect on plant diseases caused by algae and fungi.
本発明は藻菌類による植物病害に対して、新しい作用性
を有し、予防効果、治療効果を示す殺菌剤を提供するこ
とを課題とする。An object of the present invention is to provide a fungicide that has a new action and exhibits preventive and therapeutic effects against plant diseases caused by algal fungi.
前記課題を解決するために、イソニコチン酸アミド誘導
体について鋭意研究した結果、一部新規化合物を含む以
下に示す下記一般式〔■〕の化合物群かへと病や疫病な
との藻菌類による植物病害に対してすぐれた予防効果、
治療効果を示すことを見い出し、本発明を完成させるに
至った。In order to solve the above problems, as a result of intensive research on isonicotinic acid amide derivatives, we found that the group of compounds represented by the following general formula [■], including some new compounds, has been found to be effective against plants caused by algae and fungi such as Phytophthora and Phytophthora. Excellent preventive effect against diseases,
The present inventors have discovered that it exhibits therapeutic effects and have completed the present invention.
すなわち、本発明は一般式
〔式中、Ｘは水素原子または塩素原子を示し、Ｙは、Ｘ
か水素原子であるときには、塩素原子、低級アルコキシ
基、低級アルキルチオ基、シアノ基、またはニトロ基を
示し、Ｘか塩素原子であるときには低級アルキル基、低
級アルコキシ基または低級アルキルチオ基を示し、Ｒ’
は水素原子、低級アルキル基、フェニル基またはベンジ
ル基を示し、Ｒ２は水素原子、低級アルキル低級アルケ
ニル基、低級アルコキノ基、）１０ケン原子またはフェ
ノキシ基で置換されてし）でもよいフェニル基、フリル
基、チエニル基、Ｎ−置換ピラゾリル基、Ｎ−置換イミ
ダゾリル基またはＮ−置換トリアゾリル基を示し、ｎは
１または２の整数を示す。〕て表わされるイソニコチン
酸アミド誘導体を有効成分として含有することを特徴と
する藻菌類による植物病害防除剤に関するものである。That is, the present invention is based on the general formula [wherein, X represents a hydrogen atom or a chlorine atom, and Y represents
When X is a hydrogen atom, it represents a chlorine atom, a lower alkoxy group, a lower alkylthio group, a cyano group, or a nitro group, and when X is a chlorine atom, it represents a lower alkyl group, a lower alkoxy group, or a lower alkylthio group, and R'
represents a hydrogen atom, a lower alkyl group, a phenyl group or a benzyl group; group, thienyl group, N-substituted pyrazolyl group, N-substituted imidazolyl group or N-substituted triazolyl group, and n represents an integer of 1 or 2. The present invention relates to a plant disease control agent caused by algal fungi, which is characterized by containing an isonicotinic acid amide derivative represented by the following formula as an active ingredient.
一般式ＣＩ）においてＲ２か、低級アルケニル基゛、ハ
ロゲン原子で置換されたフェニル基、Ｎ−置換ピラゾリ
ル基、Ｎ−置換イミダゾリル基およびＮ−置換トリアゾ
リル基である化合物、およびＹか、シアノ基、ニトロ基
および低級アルキル基である化合物は新規化合物である
。In the general formula CI), R2 is a lower alkenyl group, a phenyl group substituted with a halogen atom, an N-substituted pyrazolyl group, an N-substituted imidazolyl group, and an N-substituted triazolyl group, and Y or a cyano group, Compounds that are nitro and lower alkyl groups are new compounds.
一般式ＣＩ）で表わされるイソニコチン酸アミド誘導体
は以下の方法によって製造することかてきる。The isonicotinic acid amide derivative represented by the general formula CI) can be produced by the following method.
一般式
〔式中、Ｘ，Ｙは前記と同じ意味を有する。〕で表わさ
れるイソニコチン酸クロライド誘導体を
一般式
〔式中、Ｒ１は前記と同じ意味を有し、Ｒ′は水素原子
、低級アルキル基、低級アルケニル基、）＼ロゲン原子
またはフェノキシ基で置換されてし゛てもよいフェニル
基、フ＋Ｊ ）し基まｔこ（まチエニル基を示す。）
で表わされるアミノアセトニトリル誘導体また（よその
塩と、場合により塩基の存在下に不活性な溶媒中で反応
させることにより得られる。General formula [wherein, X and Y have the same meanings as above]. ] The isonicotinic acid chloride derivative represented by the general formula [wherein R1 has the same meaning as above, and R' is a hydrogen atom, a lower alkyl group, a lower alkenyl group, An aminoacetonitrile derivative represented by a phenyl group (which may be a phenyl group) or (indicates a phenyl group) or (another salt and optionally a base) in an inert solvent. Obtained by reaction.
ここにいう塩基としては、トリエチルアミン、トリブチ
ルアミン、Ｎ、 Ｎ−ツメチルアニリン、Ｎメチルモル
ホリン、ピリジン、４−ジメチルアミノピリジン等の第
３級アミン、水酸化ナトリウム、水酸化カリウム、炭酸
ナトリウム、炭酸カリウム、炭酸水素ナトリウム、水素
化ナトリウム等の無機塩基かあげられる。また不活性溶
媒としては、水あるいは有機溶媒たとえばヘキサン、ヘ
プタン等の脂肪族炭化水素類、ヘンセン、トルエン等の
芳香族炭化水素類、ジクロロメタ〕、クロロホルム等の
ハロゲン化炭化水素類、ジエチルエーテル、テトラヒド
ロフラン等のエーテル類、アセトン、メチルエチルケト
ン等のケトン類、アセトニトリル、プロピオニトリル等
のニトリル類、酢酸エチル、プロピオン酸エチル等のエ
ステル類、ジメチルホルムアミド、ジメチルスルホキシ
ド等の非プロトン性極性溶媒かあげられ、さらに、ピリ
ジンは上記の塩基と溶媒を兼ねて用いることかできる。The bases mentioned here include tertiary amines such as triethylamine, tributylamine, N,N-trimethylaniline, N-methylmorpholine, pyridine, and 4-dimethylaminopyridine, sodium hydroxide, potassium hydroxide, sodium carbonate, and carbonic acid. Examples include inorganic bases such as potassium, sodium hydrogen carbonate, and sodium hydride. Examples of inert solvents include water or organic solvents such as aliphatic hydrocarbons such as hexane and heptane, aromatic hydrocarbons such as Hensen and toluene, halogenated hydrocarbons such as dichloromethane, chloroform, diethyl ether, and tetrahydrofuran. ethers such as acetone, ketones such as methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, esters such as ethyl acetate and ethyl propionate, and aprotic polar solvents such as dimethylformamide and dimethyl sulfoxide. Furthermore, pyridine can be used both as the above base and as a solvent.
また上記の溶媒を混合して用いることもてきる。反応温
度および反応時間は、−１０°Ｃ〜１００°Ｃ１好まし
くは、０°Ｃ〜５０°Ｃの範囲、約３０分〜２４時間、
好ましくは１〜８時間の範囲で行ゎ第１る。反応終了後
、常法に従い後処理を行い、必要に応して再結晶あるい
はカラムクロマトクラフィーによって精製することかで
きる。It is also possible to use a mixture of the above solvents. The reaction temperature and reaction time are in the range of -10°C to 100°C, preferably 0°C to 50°C, about 30 minutes to 24 hours,
It is preferably carried out for 1 to 8 hours. After completion of the reaction, post-treatment can be carried out according to conventional methods, and if necessary, it can be purified by recrystallization or column chromatography.
−数式（Ｉ［）て表わされるアミノアセトニトリル誘導
体は、
一般式
％式％［）
Ｃ式中、Ｒ′は前記と同し意味を有する。〕で表わされ
るアルデヒドとシアン化水素およびＲ’ＮＨ２を反応（
いわゆるストレッカー反応）さぜることにより得られる
。- The aminoacetonitrile derivative represented by the formula (I [) has the general formula % formula % [) C where R' has the same meaning as above. ] is reacted with hydrogen cyanide and R'NH2 (
(so-called Strecker reaction).
Ｒが低級アルコキシ基、Ｎ−置換ピラゾリル基、Ｎ−置
換イミダゾリル基またはＮ−置換トリアプリル基である
化合物は、以下の方法によって製造することかできる。A compound in which R is a lower alkoxy group, an N-substituted pyrazolyl group, an N-substituted imidazolyl group, or an N-substituted triaryl group can be produced by the following method.
前記方法によって得られた
〔式中、Ｘ、Ｙ、Ｒ’と前記と同し意味を有する。〕で
表わされるＮ−シアノメチルイソニコチン酸アミ゛ド誘
導体を溶媒中てノ１０ゲン化剤と反応させ一般式
〔式中、Ｘ、Ｙ、Ｒ’と前記と同じ意味を有し、Ｚはハ
ロゲン原子を示す。〕
て表わされるハロゲン化中間体を得、次いてこの中間体
を塩基の存在下
一般式
％式％
〔式中、Ｑは低級アルコキシ基、ｌ−ピラプリル基、ｌ
−イミダゾリル基、１−トリアプリル基を示す。〕
て表わされるアルコール類、アゾール類と反応させるこ
とにより得られる。obtained by the above method [wherein, X, Y, and R' have the same meanings as above. ] An N-cyanomethylisonicotinic acid amide derivative represented by the general formula [wherein X, Y, and R' have the same meanings as above, and Z is Indicates a halogen atom. [In the formula, Q is a lower alkoxy group, l-pyrapril group, l-pyrapril group,
-Imidazolyl group, 1-triaryl group. ] It can be obtained by reacting with alcohols and azoles represented by
溶媒としてはジクロロメタン、クロロホルム等の脂肪族
ハロゲン化物か好−ましく、さらに、酢酸メチル、酢酸
エチル等のエステル類を用いることかできる。ハロケン
化剤としては塩素および臭素か好ましい。反応は、０°
Ｃ−１００’Ｃ１好ましくは２０°Ｃ〜５０°Ｃて行い
、ハロゲン化中間体を単離してもよいか、通常は、単離
することなくそのままアルコール類、アゾール類と反応
させることかできる。この反応は塩基の存在下で行うの
が好ましく塩基としては、トリエチルアミン、Ｎ、 Ｎ
−ジメチルアニリン、ピリジン等の第３級アミンや炭酸
すトリウム、炭酸カリウム、炭酸水素ナトリウム、水酸
化ナトリウム、水酸化カリウム等の無機塩基等があげら
れる。反応は一１Ｏ°Ｃ〜５０°Ｃて行うのか好ましく
、常法により後処理を行い、必要に応して再結晶あるい
はカラムクロマトクラフィーによって精製することかで
きる。Preferred solvents include aliphatic halides such as dichloromethane and chloroform, and esters such as methyl acetate and ethyl acetate may also be used. Chlorine and bromine are preferred as the halosaponizing agent. The reaction is 0°
C-100'C1 Preferably, the reaction is carried out at 20°C to 50°C, and the halogenated intermediate may be isolated, or usually, it may be directly reacted with alcohols or azoles without isolation. This reaction is preferably carried out in the presence of a base, such as triethylamine, N, N
- Tertiary amines such as dimethylaniline and pyridine; inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, sodium hydroxide, and potassium hydroxide; and the like. The reaction is preferably carried out at -10°C to 50°C, post-treatment can be carried out by conventional methods, and if necessary, purification can be carried out by recrystallization or column chromatography.
本発明防除剤か優れた防除効果を示す藻菌類による植物
病害としては、ブドウのへと病（Ｐｌａｓｍ。Plant diseases caused by algae and fungi that exhibit excellent control effects with the pesticidal agent of the present invention include grape blight (Plasm).
ｐａｒａ ｖｉｔｉｃｏｌａ）、ウリ類のへと病（Ｐｓ
ｅｕｄｏｐｅｒｏｎｏｓｐｏｒａ ｃｕｂｅｎｓｉｓ）
、アブラナ科野菜のへと病（Ｐｅｒｏｎｏｓｐｏｒａ
ｂｒａｓｓｉｃａｅ） 、ネギのへと病（Ｐｅｒｏｎｏ
ｓｐｏｒａｄｅｓｔｒｕｃｔｏｒ） 、ホウレン草のへ
と病（Ｐｅｒｏｎｏｓｐ。para viticola), cucurbit blight (Ps
eudoperonospora cubensis)
, Peronospora blight of cruciferous vegetables
brassicae), green onion rot disease (Perono brassicae),
sporadestructor), spinach blight (Peronosp.
ｒａ ５ｐｉｎａｃｉａｅ）、ダイブのへと病（Ｐｅｒ
ｏｎｏｓｐｏｒａ ｍａｎ−ｓｂｕｒｉｃａ）、ソラマ
メのへと病（Ｐｅｒｏｎｏｓｐｏｒａ ｖｉｃｉａｅ）
、ホップのへと病（Ｐｓｅｕｄｏｐｅｒｏｎｏｓｐｏｒ
ａ ｈｕｍｕｌｉ）、トマト、キュウリの灰色疫病（Ｐ
ｈｙｔｏｐｈｔｈｏｒａ ｃａｐｓｉｃｉ）ジャガイモ
、トマト、ナスの疫病（Ｐｈｙｔｏｐｈｔｈｏｒａｉｎ
ｆｅｓｔａｎｓ）、パイナツプルの疫病（Ｐｈｙｔｏｐ
ｈ、ｔｈｏｒａｃ＋ｎｎａｍｏｍｉ）、タバコの疫病（
Ｐｈｙｔｏｐｈｔｈｏｒａ ｎ１ｃｏｔｉａｎａ ｖａ
ｒ、 ｎ１ｃｏｔｉａｎａ）、ピシューム属菌等による
各種作物の立枯病等が挙げられる。ra 5 pinaciae), diver's disease (Per.
onospora man-sburica), faba bean rot disease (Peronospora viciae)
, Pseudoperonospor
a humuli), gray late blight of tomatoes and cucumbers (P
phytophthora capsici) Late blight of potatoes, tomatoes, and eggplants (Phytophthora capsici)
festans), Pineapple Phytophthora (Phytop)
h, thorac+nnamomi), tobacco blight (
Phytophthora n1cotiana va
r, n1cotiana), damping-off diseases of various crops caused by Pythium genus bacteria, etc.
本発明化合物を藻菌類による植物病害防除剤の有効成分
として使用する場合、本発明化合物を１種又は２種以上
使用してもよい。When the compound of the present invention is used as an active ingredient of an agent for controlling plant diseases caused by algae and fungi, one or more compounds of the present invention may be used.
本発明化合物を藻菌類による植物病害防除剤として使用
する場合、使用目的に応してそのまま力・または効果を
助長あるいは安定にするために農薬補助剤を混用して、
農薬製造分野において一般に行われている方法により、
粉剤、細粒剤、粒剤、水和剤、フロアブル剤および乳剤
等の製造形態にして使用することかできる。When the compound of the present invention is used as a plant disease control agent caused by algae, depending on the purpose of use, it may be mixed with an agricultural chemical adjuvant to enhance or stabilize its power or effect.
By the method commonly used in the agricultural chemical manufacturing field,
It can be used in the form of powders, fine granules, granules, wettable powders, flowable preparations, emulsions and the like.
これらの種々の製剤は実際の使用に際しては直接そのま
ま使用するか、または水で所望の濃度に希釈して使用す
ることかできる。In actual use, these various formulations can be used directly or diluted with water to a desired concentration.
ここにいう農薬補助剤としては担体（希釈剤）およびそ
の他の補助剤たとえば展着剤、乳化剤、湿展剤、分散剤
、固着剤、崩壊剤等をあげることかできる。Examples of the agrochemical auxiliary agent herein include carriers (diluents) and other auxiliary agents such as spreading agents, emulsifiers, wetting agents, dispersants, fixing agents, and disintegrants.
液体担体としてはトルエン、キシレン等の芳香族炭化水
素、メタノール、ブタノール、クリコール等のアルコー
ル類、アセトン等のケトン預、ジメチルホルムアミド等
のアミド類、ンメチルスルホキシト等のスルホキシド類
、メチルナフタレン、ンタロヘキサン、動植物油、脂肪
酸、脂肪酸エステル等があげられる。Examples of liquid carriers include aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol, and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as methyl sulfoxide, methylnaphthalene, and ntalohexane. , animal and vegetable oils, fatty acids, fatty acid esters, etc.
固体担体としてはクレー、カオリン、タルク、珪藻土、
ンリカ、炭酸カルシウム、モンモリロナイト、ヘントナ
イト、長石、石英、アルミナ、鋸屑等があげられる。Solid carriers include clay, kaolin, talc, diatomaceous earth,
Examples include calcium carbonate, montmorillonite, hentonite, feldspar, quartz, alumina, and sawdust.
また乳化剤または分散剤としては通常界面活性剤か使用
され、たとえば高級アルコール硫酸ナトノウム、ステア
リルトリメチルアンモニウムクロライド、ポリオキシエ
チレンアルキルフェニルエーテル、ラウリルヘタイン等
の陰イオン系界面活性剤、陽イオン系界面活性剤、非イ
オン系界面活性剤、両回イオン系界面活性剤かあげられ
る。In addition, surfactants are usually used as emulsifiers or dispersants, such as anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, laurylhetaine, and cationic surfactants. Examples include surfactants, nonionic surfactants, and both ionic surfactants.
展着剤としてはポリオキシエチレンノニルフェニルエー
テル、ポリオキシエチレンラウリルエーテル等か、湿展
剤としてはポリオキシエチレンノニルフェニルエーテル
、ジアルキルスルホサクシネート等か、固着剤としては
カルホキジメチルセルロース、ポリヒニルアルコール等
か、崩壊剤としてはリクニンスルホン酸ナトリウム、ラ
ウリル硫酸ナトリウム等があげられる。Spreading agents include polyoxyethylene nonylphenyl ether and polyoxyethylene lauryl ether; wetting agents include polyoxyethylene nonylphenyl ether and dialkyl sulfosuccinate; and fixing agents include carboxydimethyl cellulose and polyhyperoxyethylene. disintegrants include sodium ricnin sulfonate, sodium lauryl sulfate, etc.
いずれの製剤もそのまま単独で使用できるのみならず、
他の農園芸用殺菌剤、殺虫剤、植物生長調節剤、殺ダニ
剤と混合して使用することもてきる。Not only can each formulation be used alone, but
It can also be used in combination with other agricultural and horticultural fungicides, insecticides, plant growth regulators, and acaricides.
本発明藻菌類による植物病害防除剤における有効成分化
合物含量は、製剤形態、施用する方法、その他の条件に
よって種々異なり場合によっては有効成分化合物のみて
よいか、通常は０．５〜９５９６（重量）好ましくは２
〜７０％（重量）の範囲である。The content of the active ingredient compound in the plant disease control agent caused by algae and fungi of the present invention varies depending on the formulation form, method of application, and other conditions. Preferably 2
~70% (by weight).
本発明の殺菌剤は、有効成分濃度が好ましくはｌＯ〜４
０００ｐｐｍで植物の草葉に散布することかでき土壌に
散布する場合は有効成分散布量は０．０２〜ｉｆｆｋｇ
／１０ａか好ましい。The disinfectant of the present invention preferably has an active ingredient concentration of 10 to 4
000ppm can be sprayed on the leaves of plants, and when spraying on soil, the amount of active ingredient sprayed is 0.02~iffkg
/10a is preferable.
本発明に係る藻菌類による植物病害防除剤は、へと病や
疫病に対して、優れた予防効果、治療効果を有し、さら
に薬剤耐１生菌の出現により防除効果か低下している場
面でも十分な防除効果か期待てきる。このように本発明
に係る藻菌類による植物病害防除剤は優れた特性を具備
しており、有用である。The agent for controlling plant diseases caused by algae and fungi according to the present invention has excellent preventive and therapeutic effects against flatworm and late blight, and furthermore, in situations where the control effect is reduced due to the appearance of drug-resistant viable bacteria. However, I am hopeful that it will have a sufficient control effect. As described above, the plant disease control agent using algae and fungi according to the present invention has excellent properties and is useful.
以下にイソニコチン酸アミド誘導体の参考合成例をあげ
て具体的に示す。Reference synthesis examples of isonicotinic acid amide derivatives will be specifically described below.
参考合成例１゜
２−（２−クロロイソニコチニルアミノ）−４メチル−
３−ペンチンニトリル（Ｎｏ、３）の合成。Reference synthesis example 1゜2-(2-chloroisonicotinylamino)-4methyl-
Synthesis of 3-pentynenitrile (No, 3).
２−アミノ−４−メチル−３−ペンテンニトリル１．９
８ｇ（１８，０ミリモル）、トリエチルアミン２ ｒＪ
（１４，４ミリモル）、アセトニトリル３０ｍＦの溶液
に、０°Ｃに保ちなから２−クロロイソニコチン酸クロ
ライド２．１ｇ（１１，９ミリモル）を滴下した。室温
で１．５時間攪拌後、水中てこ注ぎ酢酸エチルで抽出し
た。2-amino-4-methyl-3-pentenenitrile 1.9
8 g (18,0 mmol), triethylamine 2 rJ
(14.4 mmol) and 2.1 g (11.9 mmol) of 2-chloroisonicotinic acid chloride was added dropwise to a solution of 30 mF acetonitrile while keeping the temperature at 0°C. After stirring at room temperature for 1.5 hours, the mixture was poured into water and extracted with ethyl acetate.
有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムて乾
燥しＴこ後、溶媒を留去し、得られた粗生成物をノリカ
ケルカラムクロマトクラフィーにより精製して、２−（
２−クロロイソニコチニルアミノ）−４−メチル−３−
ペンチンニトリルＬｌ、３ｇ（収率４３．３９ゎ）を得
た。The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, the solvent was distilled off, and the resulting crude product was purified by Norikakel column chromatography to obtain 2-(
2-chloroisonicotinylamino)-4-methyl-3-
3 g (yield: 43.39㎎) of pentynitrile L1 was obtained.
ｍ、ｐ、 ８５〜８６°Ｃ
参考合成例２
２−（２−り０ロイソニコチニルアミノ）−２（ＩＩ（
−１，２，４−トリアゾール−１−イル）アセトニトリ
ル（Ｎｏ、Ｉ４）の合成
Ｎ−（シアノメチル）−２−クロロイソニコチン酸アミ
ド８ ｇ（４０，９ミリモル）、乾燥酢酸エチル１４０
ｍ１を加熱攪拌し結晶を溶解した後に、５０〜５５°Ｃ
に保ちながら臭素２．２ｍｌを滴下した。１０分間攪拌
し、窒素ガスを吹き込み、生成した臭化水素を除去した
後、５°Ｃ以下に冷却し、ＩＨ−１，２，４トリアゾー
ル５．９３ｇ（８５，９ミリモル）を加えた。ひき続き
、同温度でトリエチルアミン１２ｍ１を滴下しその後室
温で２時間攪拌した。飽和食塩水を加え有機層を無水硫
酸すｈ ＩＪウムて乾燥した後、溶媒を留去し、得られ
た粗生成物をシリカゲルクロマトクラフィーにより精製
して、２−（２−クロロイソニコチニルアミノ） −２
−（ＩＨ−１，２，４−トリアゾール−１−イル）アセ
トニトリル４．３ｇ（収率４０％）を得た。m, p, 85-86°C Reference synthesis example 2 2-(2-ri0leusonicotinylamino)-2(II(
Synthesis of -1,2,4-triazol-1-yl)acetonitrile (No, I4) N-(cyanomethyl)-2-chloroisonicotinic acid amide 8 g (40,9 mmol), dry ethyl acetate 140
After heating and stirring m1 to dissolve the crystals, heat to 50-55°C.
2.2 ml of bromine was added dropwise while maintaining the temperature. After stirring for 10 minutes and blowing nitrogen gas to remove generated hydrogen bromide, the mixture was cooled to below 5°C, and 5.93 g (85.9 mmol) of IH-1,2,4 triazole was added. Subsequently, 12 ml of triethylamine was added dropwise at the same temperature, followed by stirring at room temperature for 2 hours. After adding saturated brine and drying the organic layer over anhydrous sulfuric acid, the solvent was distilled off, and the resulting crude product was purified by silica gel chromatography to obtain 2-(2-chloroisonicotinyl). amino) -2
-(IH-1,2,4-triazol-1-yl)acetonitrile 4.3g (yield 40%) was obtained.
ｍ、ｐ、 １８６〜１８８°Ｃ
参考合成例３
Ｎ−（シアノメチル）−２−クロロ−６−メチルイソニ
コチン酸アミド（Ｎｏ、 ２７）の合成：水酸化ナトリ
ウム２．４ｇ（５６ミリモル）を水２４ｍｊに溶解し、
この溶液にアミノアセトニトリル硫酸塩３．６ｇ（１７
ミリモル）を加えた後、５°Ｃ以下て２−クロロ−６−
メチルイソニコチン酸クロライド３、２３ｇ （１７
ミリモル）のエーテル（３０ｙｄ ）溶液を滴下した。m, p, 186-188°C Reference synthesis example 3 Synthesis of N-(cyanomethyl)-2-chloro-6-methylisonicotinic acid amide (No. 27): 2.4 g (56 mmol) of sodium hydroxide was added to water. Dissolved in 24mj,
Add 3.6 g (17 g) of aminoacetonitrile sulfate to this solution.
2-chloro-6-
Methylisonicotinic acid chloride 3.23g (17
A solution of 30 mmol) in ether (30 yd) was added dropwise.
その後室温にて２時間攪拌し、反応液を水にあけ、酢酸
エチルで抽出した。有機層を飽和食塩水で洗い、無水硫
酸ナト１，１ウムて乾燥した後、溶媒を濃縮し、得られ
た粗生成物をシリカゲルクロマトクラフィーにより精製
して、Ｎ−（シアンメチル）−２−クロロ−６−メチル
イソニコチン酸アミド２．４ｇ（収率７６．１％）を得
た。Thereafter, the mixture was stirred at room temperature for 2 hours, and the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over 1.1 um of anhydrous sodium sulfate, the solvent was concentrated, and the resulting crude product was purified by silica gel chromatography to obtain N-(cyanmethyl)-2. 2.4 g (yield 76.1%) of -chloro-6-methylisonicotinic acid amide was obtained.
ｍ、ｐ、 １２４〜１２５ °Ｃ一般式数式）
で表わされるイソニコチ〉酸アミド誘導体の代表例を物
性値とともに第１表に示すＹ／′−
以下に製剤例を示すか、農薬補助剤の種類および混合比
率はこれらのみて限定されることなく、広い範囲で使用
可能である。なお「部」とあるのは重量部を意味する。m, p, 124-125 °C (general formula)
Typical examples of isonicotinic acid amide derivatives represented by Y/' are shown in Table 1 along with their physical properties. Can be used in a wide range. Note that "parts" means parts by weight.
製剤例１． 粉 剤
化合物Ｎｏ、 ３．２部およびクレー９８部を混合粉砕
し、粉剤とする。Formulation example 1. Powder Compound No. 3.2 parts and 98 parts of clay were mixed and ground to obtain a powder.
製剤例２． 水和剤
化合物Ｎｏ、１１．２０部とカオリン７５部と高級アル
コール硫酸ナトリウム３部およびリグニンスルホン酸ナ
トリウム２部とを混合粉砕し水和剤とする。Formulation example 2. Wettable powder compound No. 11.20 parts, 75 parts of kaolin, 3 parts of higher alcohol sodium sulfate, and 2 parts of sodium ligninsulfonate are mixed and ground to obtain a wettable powder.
製剤例３． 粒 剤
微粉砕した化合物Ｎ０９６．８部、珪藻土３６部ベント
ナイト２４部、タルク３０部および崩壊剤２部を混合し
た後、水１８部を加え、均等に湿潤させ次に射出成形機
を通して押し出し、造粒し、製粒機て整粒した後、乾燥
し粉径０．６ｍｍ〜１ｍｍの粒剤とする。Formulation example 3. After mixing 96.8 parts of finely ground compound N0, 36 parts of diatomaceous earth, 24 parts of bentonite, 30 parts of talc and 2 parts of disintegrating agent, 18 parts of water was added, the mixture was evenly moistened, and then extruded through an injection molding machine to form a mixture. After granulating and sizing using a granulator, it is dried to form granules with a powder diameter of 0.6 mm to 1 mm.
製剤例４． 微粒剤
化合物Ｎｏ、２７．５部をメタノール５部に溶かし８０
〜２５０メツシユの粒状クレー９５部に混合滴下した後
乾燥し微粒剤とする。Formulation example 4. Dissolve 27.5 parts of fine granule compound No. 80 in 5 parts of methanol.
The mixture is mixed and dropped into 95 parts of granular clay of ~250 meshes, and then dried to form fine granules.
製剤例５． 乳 剤
化合物Ｎｏ、２２．３０部をキシレン５２部に溶解し、
これにアルキルフェノールエチレンオキシド縮合物とア
ルキルヘンセンスルホン酸カルシウムの混合物（８・２
）１８部を混合溶解して乳剤とする。Formulation example 5. Emulsion compound No. 22.30 parts was dissolved in 52 parts of xylene,
To this was added a mixture of alkylphenol ethylene oxide condensate and calcium alkylhensene sulfonate (8.2
) are mixed and dissolved to form an emulsion.
本則は水で薄めて、乳濁液として使用する。The basic rule is to dilute it with water and use it as an emulsion.
次に本発明の効果に関する試験例を示す。Next, test examples regarding the effects of the present invention will be shown.
試験例１．ブドウペと病防除試験（予防効果）鉢植え（
径１０ａｎ）のブドウの葉に製剤例２，５と同等に製造
した本発明の水和剤及び乳剤を所定濃度に希釈し噴霧し
た。薬剤風乾後にへど病（Ｐｌａｓｍｏｐａｒａ ｖｉ
ｔｉｃｏｌａ）の水性胞子懸濁液を接種し、２０°Ｃ〜
２２°Ｃ１湿度１００％の接種箱内に２日間引き続き温
室内（２０°Ｃ〜３０°Ｃ）に７日間放置したのち発病
程度を調査した。Test example 1. Grape blight and disease control test (preventive effect) potted plants (
The hydrating agent and emulsion of the present invention prepared in the same manner as in Formulation Examples 2 and 5 were diluted to a predetermined concentration and sprayed onto grape leaves having a diameter of 10 ann. Plasmopara vi
ticola) and inoculated with an aqueous spore suspension of 20°C.
The seeds were left in an inoculation box at 22°C and 100% humidity for 2 days and then in a greenhouse (20°C to 30°C) for 7 days, and then the degree of disease onset was investigated.
結果は第２表に示した。The results are shown in Table 2.
第
表
ヨ＊ 発病程度
０：病斑なし
ｌ 病斑面積率５％以下
２ 〃 ５−’ａ％
３、 〃 顆へ印％
４ 〃 艶％以上
＊＊・対照薬剤
［水相剤（テトラクロルイソフタロニトリル）商品名、
ダコニール永和剤
試験例２．ブドウへと病防除試験（治療効果）鉢植え（
径１０ｃｍ）のブドウの葉にへど病（Ｐｌａｓｍｏｐａ
ｒａ Ｖｉｔｉｃｏｌａ）の水性胞子懸濁液を接種し２
０°Ｃ〜２２°Ｃ１湿度１００％の接種箱内に２日間放
置後、製剤例２，５と同等に製造した本発明の水和剤及
び乳剤を所定濃度に希釈し噴霧した。さらに温室内（２
０°Ｃ〜３０°Ｃ）に７日間放置したのち発病程度を調
査した。Table 1 * Degree of onset: 0: No lesions l Lesion area rate 5% or less 2 5-'a% 3, Mark on condyle % 4 Gloss % or more** Control drug [aqueous phase agent (tetrachlor) isophthalonitrile) product name,
Daconil permanent agent test example 2. Disease control test (therapeutic effect) on grapes (
Plasmopa on leaves of grapes with a diameter of 10 cm
ra Viticola) was inoculated with an aqueous spore suspension.
After being left in an inoculation box at 0°C to 22°C and 100% humidity for 2 days, the wettable powder and emulsion of the present invention prepared in the same manner as in Formulation Examples 2 and 5 were diluted to a predetermined concentration and sprayed. Furthermore, inside the greenhouse (2
After being left at 0°C to 30°C for 7 days, the degree of disease onset was investigated.
結果は第３表に示した。The results are shown in Table 3.
第
表
発病日！
０・発病なし
ｌ・発病面積率５％以下
２、 〃 ５寸％
３： 〃 々〜印％
４： 〃 艶％以上
対照薬削
メタラキシル士マンセプ昆合削ｇ名：リドミルＭＺｙｈ
木済０（１０％＋５５％）
牛看旧土原ル（日オイヒ馬褥式Ｘ埒土The first day of illness! 0・No disease onset l・Infection area rate 5% or less 2, 〃 5 cm% 3: 〃 ~ mark % 4: 〃 Gloss% or more
Mokusai 0 (10% + 55%) Gyukan old Dowararu
Claims (1)
が水素原子であるときには塩素原子、低級アルコキシ基
、低級アルキルチオ基、シアノ基またはニトロ基を示し
、Ｘが塩素原子であるときには低級アルキル基、低級ア
ルコキシ基または低級アルキルチオ基を示し、Ｒ＾１は
水素原子、低級アルキル基、フェニル基またはベンジル
基を示し、Ｒ＾２は水素原子、低級アルキル基、低級ア
ルケニル基、低級アルコキシ基、ハロゲン原子またはフ
ェノキシ基で置換されていてもよいフェニル基、フリル
基、チエニル基、Ｎ−置換ピラゾリル基、Ｎ−置換イミ
ダゾリル基またはＮ−置換トリアゾリル基を示し、ｎは
１または２の整数を示す。〕で表わされるイソニコチン
酸アミド誘導体を有効成分として含有することを特徴と
する藻菌類による植物病害防除剤。[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [I] [In the formula, X represents a hydrogen atom or a chlorine atom, and Y represents
When X is a hydrogen atom, it represents a chlorine atom, a lower alkoxy group, a lower alkylthio group, a cyano group, or a nitro group, and when X is a chlorine atom, it represents a lower alkyl group, a lower alkoxy group, or a lower alkylthio group, and R^1 is Represents a hydrogen atom, a lower alkyl group, a phenyl group or a benzyl group, and R^2 is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group, a phenyl group optionally substituted with a halogen atom or a phenoxy group, or furyl. group, thienyl group, N-substituted pyrazolyl group, N-substituted imidazolyl group or N-substituted triazolyl group, and n represents an integer of 1 or 2. ] A plant disease control agent caused by algae and fungi, characterized by containing an isonicotinic acid amide derivative represented by the following as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23049590A JPH04112872A (en) | 1990-09-03 | 1990-09-03 | Plant phycomycete disease control agent containing isonicotinic acid derivative as active ingredient |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23049590A JPH04112872A (en) | 1990-09-03 | 1990-09-03 | Plant phycomycete disease control agent containing isonicotinic acid derivative as active ingredient |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04112872A true JPH04112872A (en) | 1992-04-14 |
Family
ID=16908668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23049590A Pending JPH04112872A (en) | 1990-09-03 | 1990-09-03 | Plant phycomycete disease control agent containing isonicotinic acid derivative as active ingredient |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04112872A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0953565A3 (en) * | 1998-05-01 | 2002-12-04 | Nihon Nohyaku Co., Ltd. | Aminoacetonitrile derivative, agricultural and horticultural insecticide containing the same, and use thereof |
| WO2004024704A1 (en) * | 2002-09-11 | 2004-03-25 | Novartis Ag | Organic compounds |
| WO2009011305A1 (en) * | 2007-07-13 | 2009-01-22 | Sumitomo Chemical Company, Limited | Amide compound and method for controlling plant disease using the same |
-
1990
- 1990-09-03 JP JP23049590A patent/JPH04112872A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0953565A3 (en) * | 1998-05-01 | 2002-12-04 | Nihon Nohyaku Co., Ltd. | Aminoacetonitrile derivative, agricultural and horticultural insecticide containing the same, and use thereof |
| EP1445251A1 (en) * | 1998-05-01 | 2004-08-11 | Nihon Nohyaku Co., Ltd. | Aminoacetonitrile derivative, agricultural and horticultural insecticitde containing the same, and use thereof |
| WO2004024704A1 (en) * | 2002-09-11 | 2004-03-25 | Novartis Ag | Organic compounds |
| WO2009011305A1 (en) * | 2007-07-13 | 2009-01-22 | Sumitomo Chemical Company, Limited | Amide compound and method for controlling plant disease using the same |
| JP2009040775A (en) * | 2007-07-13 | 2009-02-26 | Sumitomo Chemical Co Ltd | Amide compound and its plant disease control application |
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