JPS62249975A - Anilide derivative and germicide containing said derivative as active ingredient - Google Patents
Anilide derivative and germicide containing said derivative as active ingredientInfo
- Publication number
- JPS62249975A JPS62249975A JP9259286A JP9259286A JPS62249975A JP S62249975 A JPS62249975 A JP S62249975A JP 9259286 A JP9259286 A JP 9259286A JP 9259286 A JP9259286 A JP 9259286A JP S62249975 A JPS62249975 A JP S62249975A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- formulas
- tables
- methyl
- solvent
- 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
- 239000004480 active ingredient Substances 0.000 title claims abstract description 11
- 150000003931 anilides Chemical class 0.000 title claims description 10
- 230000002070 germicidal effect Effects 0.000 title abstract 3
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 14
- 239000000645 desinfectant Substances 0.000 claims 1
- 230000001954 sterilising effect Effects 0.000 claims 1
- 238000004659 sterilization and disinfection Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 15
- -1 carboxylic acid halide Chemical class 0.000 abstract description 13
- 241000196324 Embryophyta Species 0.000 abstract description 10
- 239000002904 solvent Substances 0.000 abstract description 10
- 241000209140 Triticum Species 0.000 abstract description 5
- 235000021307 Triticum Nutrition 0.000 abstract description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 4
- 238000009835 boiling Methods 0.000 abstract description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract description 4
- 241000221198 Basidiomycota Species 0.000 abstract description 3
- 244000005700 microbiome Species 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 230000035515 penetration Effects 0.000 abstract description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- MFHROBYDUTYIJH-UHFFFAOYSA-N 2-methyl-3-propan-2-yloxyaniline Chemical compound CC(C)OC1=CC=CC(N)=C1C MFHROBYDUTYIJH-UHFFFAOYSA-N 0.000 abstract 1
- 241001617088 Thanatephorus sasakii Species 0.000 abstract 1
- 244000052616 bacterial pathogen Species 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 238000007710 freezing Methods 0.000 abstract 1
- 230000008014 freezing Effects 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000005012 migration Effects 0.000 abstract 1
- 238000013508 migration Methods 0.000 abstract 1
- 230000001717 pathogenic effect Effects 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 201000010099 disease Diseases 0.000 description 11
- 241000209094 Oryza Species 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 235000007164 Oryza sativa Nutrition 0.000 description 9
- 235000009566 rice Nutrition 0.000 description 9
- 239000000417 fungicide Substances 0.000 description 8
- 230000000855 fungicidal effect Effects 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 239000004927 clay Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 239000000440 bentonite Substances 0.000 description 3
- 229910000278 bentonite Inorganic materials 0.000 description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 230000002262 irrigation Effects 0.000 description 3
- 238000003973 irrigation Methods 0.000 description 3
- 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 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 229910052814 silicon oxide Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241000959260 Typhula Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 244000000005 bacterial plant pathogen Species 0.000 description 2
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZVXKYWHJBYIYNI-UHFFFAOYSA-N 1h-pyrazole-4-carboxamide Chemical compound NC(=O)C=1C=NNC=1 ZVXKYWHJBYIYNI-UHFFFAOYSA-N 0.000 description 1
- ANMPRMFIJIIMFE-UHFFFAOYSA-N 2-(fluoromethyl)benzoyl chloride Chemical compound FCC1=CC=CC=C1C(Cl)=O ANMPRMFIJIIMFE-UHFFFAOYSA-N 0.000 description 1
- QMGBIPKOKCSUCL-UHFFFAOYSA-N 3-propan-2-yloxyaniline Chemical compound CC(C)OC1=CC=CC(N)=C1 QMGBIPKOKCSUCL-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 235000021537 Beetroot Nutrition 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241000998584 Nuda Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 241000918585 Pythium aphanidermatum Species 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 244000250129 Trigonella foenum graecum Species 0.000 description 1
- 235000001484 Trigonella foenum graecum Nutrition 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- PANBYUAFMMOFOV-UHFFFAOYSA-N sodium;sulfuric acid Chemical compound [Na].OS(O)(=O)=O PANBYUAFMMOFOV-UHFFFAOYSA-N 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は、新規なアニリド誘導体およびそれを有効成分
として含有する殺菌剤に関する０〈従来の技術〉
従来、例えば、力μホキシン、メプロニルおよび特開昭
６０−８４９４９号公報に記載のアニリド誘導体が殺菌
剤の有効成分として用いうろことが知られている。Detailed Description of the Invention <Industrial Application Field> The present invention relates to a novel anilide derivative and a fungicide containing the same as an active ingredient. It is known that the anilide derivative described in JP-A-60-84949 can be used as an active ingredient of a fungicide.
〈発明が解決しようとする問題点〉
しかしながら、これらのアニリド読導体は、殺菌活性が
充分とは言い難く必ずしも満足すべきものではない◎
〈問題を解決するための手段〉
本発明者らは、このような状況に鑑み、優れた殺菌活性
を有する化合物を開発すべく種々検討した結果、２−メ
チ／Ｌ／−８−イソプロポキシアニリド誘導体が、上記
のような欠点の少ない、優れた殺菌活性を有することを
見出し本発明に至った。<Problems to be Solved by the Invention> However, these anilide reading conductors are not necessarily satisfactory as their bactericidal activity cannot be said to be sufficient. <Means for Solving the Problems> The present inventors have solved this problem. In view of this situation, we conducted various studies to develop a compound with excellent bactericidal activity. As a result, we found that 2-methy/L/-8-isopropoxyanilide derivative has excellent bactericidal activity with few of the above-mentioned drawbacks. This discovery led to the present invention.
すなわち、本発明は、一般式［Ｉ］
または相異なり、水素原子、ハロゲン原子、メチ１ｖＩ
Ａ；ｔたけトリフルオロメチル基を表わす０）で示され
る基を表わすＯ〕
で示される２−メチ／Ｌ／−８−イソプロボキＶアニリ
ド誘導体（以下、本発明化合物と称する０）およびそれ
を有効成分として含有する殺菌剤を提供するものである
Ｏ
本発明化合物は、種々の植物病原菌、特に担子菌類に属
する微生物による植物病害に対して予防的、活療的、浸
透移行的殺菌効力を有することから殺菌剤の有効成分と
して用いることができる０
本発明化合物が優れた効力を有する植物病害としては、
例えばイネの紋枯病（Ｒｈｉｚｏｃｔｏｎｌａｓｏｌａ
ｎｉ ）、疑似紋枯病（Ｒｈｌｚｏｅｔｏｎｌａ ｏｒ
ｙ＊＊ｅ、 Ｒ。That is, the present invention relates to the general formula [I] or, differently, a hydrogen atom, a halogen atom, a methyl
A; O representing a group represented by 0) representing a trifluoromethyl group] A 2-methy/L/-8-isoproboxyV anilide derivative (hereinafter referred to as the compound of the present invention) represented by O The compound of the present invention, which provides a fungicide contained as a component, has preventive, curative, and systemic bactericidal effects against plant diseases caused by various plant pathogenic bacteria, particularly microorganisms belonging to Basidiomycetes. The plant diseases for which the compound of the present invention has excellent efficacy include the following:
For example, rice sheath blight (Rhizocton lasola)
ni), pseudosheath blight (Rhlzoetonla or
y**e, R.
ｍｏｌａｎｌ Ｗ Ｂ ｑ ） 、ムギ類のさび病（Ｐ
ｕｃｅｌｎｌｍｓｔｒｉｌｆｏｒｍｌｓ 、Ｐ、
ｇｒａｍｉｎｌｓ 、Ｐ、 ｒｅｃｏｎｄｌｔａ
、 Ｐ。molanl W Bq), wheat rust (P
ucelnlmstrilforms,P,
gramins, P. recondlta
, P.
ｈｏｒｄ＠ｌ ）、雪腐病（Ｔｙｐｈｕｌａ １ｎｅａ
ｒｎａｔａ、 Ｔ。hord@l ), snow rot (Typhula 1nea
rnata, T.
量ｓｈｌｋａｒｌｅｎｓ１ｍ ）、裸黒穂病（Ｕｓｔｌ
ｌａｇｏ ｔｒ口ｉｅｉ。amount shlkarlens1m), naked smut (Ustl
Lago tr mouth iei.
Ｕ、 ｎｕｄａ）、各種作物の立枯病（Ｒｈｉｚｏｅｔ
ｏｎｌｍｓｏｌａｎｉ ）、白絹病（Ｃｏｒｔｉｏｌｕ
ｍ ｒｏｌｆｇｉｌ）、ジャガイモ、ビートのりジフト
ニア病（Ｒｈｉｚｏｅｔｏｎｉｍｓｏｌａｎｌ ）、ナ
シの赤星病（Ｇｙｍｎｏａｐｏｒａｎｇｌｕｍ ｈａｒ
ａｏａｎｕｍ）リンゴの黒星病（Ｖ＠ｎｔｕｒｉｓ ｌ
ｎａｓｑｕａｒｌｇ）、牧草、芝生等の葉腐病（Ｒｈｌ
ｚｏａｔｏｎｉａ ５ｏｌａｎｌ ）、白絹病（Ｃｏｒ
ｔｉｅｌｕｍ ｒｏｌｆｓｌｌ ）１１葉さび病（Ｕｒ
ｏｍｙａｅｍｔｒｌｆｏｌｉｌ ）、雪腐病（Ｔｙｐｈ
ｕｌａ １ｎｃａｒｎａｔａ、 Ｔ。U, nuda), damping-off disease of various crops (Rhizoet
onlmsolani), white silk disease (Cortiolu
m rolfgil), potato, beetroot diphtonia (Rhizoetonimsolanl), pear red star disease (Gymnoaporanglum har)
aoanum) apple scab disease (V@nturis l)
nasquarlg), leaf rot disease of grasses, lawns, etc. (Rhl
zoatonia 5olanl), white silk disease (Cor
tielum rolfsll) 11 Leaf rust (Ur
omyaemtrlfolil), snow rot (Typh
ula 1ncarnata, T.
１ｓｈｉｋａｒｌｅｎｓ１ｍ ）等が挙げられる０本発
明化合物を殺菌剤の有効成分として用いる場合は、他の
何らの成分も加えずそのまま用いてもよいが、通常は、
固体担体、液体担体、界面活性剤その他の製剤用補助剤
と混合して、乳剤、水利剤、懸濁剤、粒剤、粉剤、液剤
等に製剤して用いる。When using the compound of the present invention as an active ingredient of a fungicide, it may be used as it is without adding any other ingredients, but usually,
It is used by mixing with solid carriers, liquid carriers, surfactants, and other formulation auxiliaries to formulate emulsions, aqueous agents, suspensions, granules, powders, liquids, etc.
これらの製剤中の有効成分としての本発明化合物の含有
量は、ｖ′１に比テ０．１〜９９．９ ＊、好ましくけ
０．２〜８０％の範囲である。The content of the compound of the present invention as an active ingredient in these preparations is in the range of 0.1 to 99.9*, preferably 0.2 to 80%, relative to v'1.
上記製剤において、固体担体としては、カオリンクレー
、アッタバルジャイトクレー、ベントナイト、酸性白土
、パイロフィライト、タルク、珪藻土、方解石、トウモ
ロコＶ穂軸粉、クルミ殻粉、尿素、硫酸アンモニウム、
合成含水酸化珪素等の微粉末あるいは粒状物があげられ
、液体担体としては、キシレン、メチルナフタレン等の
芳香族膨化水素類、イソプロパツール、エチレングリコ
ール、セｐソμプ等のアルコール類、ア十トン、シクロ
ヘキサノン、イソホロン等のケトン類、大豆油、ｆ／ｉ
ｌ実油等の植物油、ジメチルスルホキシト、アセトニト
リμ、水篩があげられる〇
乳化、分散、湿展等のために用いられる界面活性剤とし
ては、アルキ／Ｉ／硫酸エステ／Ｉ／塩、アルキ／Ｉ／
（アリ−／Ｌ／）ス／Ｉ／由ン酸塩、シアルキ〜ス〃ホ
こけ〈酸塩、ポリオキシエチレンアルキルアリーｐエー
テルシん酸二７テＪ” 塩、ナフタレンスルホン酸ホ〃
マリン縮合物等の陰イオン界面活性剤、ポリオキシエチ
レンアルキルエーテル、ポリオキシエチレンポリオキシ
プロ上０レンブロツクコボリマー、ソルビタン脂肪酸エ
ステル、ポリオキシエチレンソルビタン脂肪酸エステル
等の非イオン界面活性剤等があげられるＯ膨剤用補助剤
としては、リグニンスルホン酸塩、アルギン酸塩、ポリ
ビニルアルコール、アラビアガム、ＣＭＣ（カルボキシ
メチルセルロー、ｚ）、ＰＡＰ（酸性りん酸イソプロピ
ｌｖ）等があげられる。In the above formulation, the solid carriers include kaolin clay, attabulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn V cob powder, walnut shell powder, urea, ammonium sulfate,
Examples include fine powders or granules such as synthetic hydrous silicon oxide, and liquid carriers include aromatic swollen hydrogens such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and sepsoprop. Juton, cyclohexanone, ketones such as isophorone, soybean oil, f/i
Examples of surfactants used for emulsification, dispersion, wet spreading, etc. include alkyl/I/sulfuric acid ester/I/salt, alkyl /I/
(Ary-/L/)su/I/ phosphate, sialkyl aryp ether sulfonate, polyoxyethylene alkyl aryp ether sulfonate diphosphate, naphthalene sulfonate
Examples include anionic surfactants such as marine condensates, nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene polyoxypropylene block copolymer, sorbitan fatty acid ester, and polyoxyethylene sorbitan fatty acid ester. Examples of adjuvants for the O swelling agent include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose, z), PAP (isopropyl acid phosphate lv), and the like.
これらの製剤は、希釈せずそのまま、または例えば水で
希釈して植物体に直接施用するかあるいは土壊に施用す
る０さらに詳しくは植物体へ散布または散粉するか、土
壌表面へ散布、散粉または散粒するか、あるいは必要に
応じその後さらに土壊と混和するなど種々の形態で使用
される０
また、他の殺菌剤と混合して用いることにより、殺菌効
力の増強をも期待できる。さらに、殺虫剤、殺ダニ剤、
殺線虫剤、除草剤、植物生長調節剤、肥料、土壊改良剤
と混合して用いることもできる。These preparations can be applied undiluted or, for example, diluted with water, directly to plants or applied to soil damage. It can be used in various forms, such as by scattering it, or by mixing it with soil destruction if necessary.In addition, it can be expected to increase its bactericidal efficacy by mixing it with other bactericidal agents. In addition, insecticides, acaricides,
It can also be used in combination with nematicides, herbicides, plant growth regulators, fertilizers, and soil damage improvers.
なお、本発明化合物は、水田、畑地、果樹園、牧草地、
芝生地等の殺菌剤の有効成分として用いることができる
◎
本発明化合物を殺菌剤の有効成分として用いる場合、そ
の施用量は、気象条件、製剤形態、施用時期、方法、場
所、対象病害、対象作物等によっても異なるが、通常１
アールあたシ０．６〜１００２、好ましくは、１ｆ〜５
０ｆであシ、乳剤、水利剤、懸濁剤、液剤等を水で希釈
して施用する場合、その施用濃度は、０．００１％〜１
％、好ましくは、０．００５％〜０．５％であシ、また
粒剤、粉剤等（住、なんら希釈することなくそのまま施
用する〇
本発明化合物としては、例えば次のようなものが挙げら
れる。The compound of the present invention can be used in rice fields, fields, orchards, pastures,
It can be used as an active ingredient of a fungicide for lawns, etc. ◎ When the compound of the present invention is used as an active ingredient of a fungicide, the amount of application should be determined depending on weather conditions, formulation form, application time, method, location, target disease, and target. Although it varies depending on the crop etc., usually 1
R at 0.6 to 1002, preferably 1f to 5
When applying 0f, emulsions, irrigation agents, suspensions, liquids, etc. diluted with water, the application concentration is 0.001% to 1%.
%, preferably 0.005% to 0.5%, as well as granules, powders, etc. (apply as is without any dilution) Examples of the compounds of the present invention include the following: It will be done.
２−メチル−Ｎ−（２−メチル−８−イソプローキシフ
ェニル）フラン−８−カルボキサミド
２−トリフルオロメチｐ−Ｎ−（２−メチμｍ８−イソ
ブロポキシフエニ／Ｉ／）フラン−８−カルボキサミド
２．５−ジメチル−Ｎ−（２−メチ／Ｌ’−８−イソブ
ｐボキシフェニｌＬ／）フラン−８−カルボキサミド
５−メチル−２−トリフルオロメチル−Ｎ−（２−メチ
Ａ／−８−イソプロボキンフエニ／Ｌ／）フラン−８−
カルボキサミド
２−メチル−Ｎ−（２−メチ／Ｌ’−８−イソプロボキ
ＶフェニＡ／）チオフェン−８−カルボキサミド
２−トリフルオロメチル−Ｎ−（２−メチル−８−イソ
プロボキシフエニ／Ｉ／）チオフェン−８−カルボキサ
ミド
２．５−ジメチμ−Ｎ−（２−メチル−８−イソブロボ
キＶフェニル）チオフェン−８−力〃ボキサミド
５−メチル−２−トリフルオロメチル−Ｎ−（２−メチ
ｌＬ／−８−イソブロボキシフエニ／Ｌ／）チオフェン
−８−カルボキサミド
８−メチル−Ｎ−（２−メチ／Ｌ／−８−イソプロポキ
シフェニμ）チオフェン−２−カルボキサミド
８−トリフルオロメチル−Ｎ−（２−メチル−８−イソ
ブロボキシフェニμ）チオフェン−８−力μボキサミド
８．５−ジメチル−Ｎ−（２−メチ／Ｉ／−８−イソプ
ロボキシフェニ／Ｌ／）チオフェン−２−カルボキサミ
ド
５−メチｙｖ−８−）リフルオロメチル−Ｎ＝（２−メ
チ／ｌ／−８−イソブロポキシフェニ／Ｉ／）チオフェ
ン−２−カルボキサミド
１．８−ジメチμ−Ｎ−（２−メチ／Ｉ／−８−イソプ
ロポキシフェニ／Ｉ／）ビクゾー／Ｌ’−４−カルボキ
サミド
１．５−ジメチμ−Ｎ−（２−メチ／Ｌ’−８−イソプ
ロポキシフェニ／Ｌ／）ピラシー／Ｌ／−４−力ルボキ
サミド
１−メチ／Ｌ’ −８−）リフルオロメチル−’Ｎ −
（２−メチＡ／−８−イソプロポキシフェニ／Ｉ／）ピ
ッジー／ｌ／−４−カルボキサミド
１−メチ／Ｌ’−５−）リフルオロメチル−Ｎ−（２−
メチ／Ｉ／−８−イソプロボキシフェニ／Ｌ／）ピッジ
ー／ｌ／−４−カルボキサミド
１．８．５−）リメチルーＮ−（２−メチル−８−イソ
プロポキシフェニ／ｌ／）ピラゾール−４−カμボキサ
ミド
１．８−ジメチ１ｖ−５−）リフルオロメチル−Ｎ−（
２−メチル−８−イソプロボキシフェ二／Ｌ／）ピラシ
ー／Ｌ’−４−カルボキサミド１．５−ジメチル−８−
トリフルオロメチル−Ｎ−（２−メチ／Ｉ／−８−イソ
プロポキシフェニμ）ヒラシー／ｌ／−４−カルボキサ
ミド５−クロロ−１，８−ジメチμ−Ｎ−（２−メチ１
ｖ−８−イソプロポキシフェニル）ピッジー／ｌ／−４
−カルボキサミド
１．８−ジメチＡ／−５−フルオロ−Ｎ −（２−メチ
）ｖ−３−イソプロボキシフェニ／ｌ／）ピッジー／ｌ
／−４−カルボキサミド
３−クロロ−１，５−ジメチル−Ｎ−（２−メチ１ｖ−
Ｂ−イソプロポキンフェニル）ピッジー／Ｌ’−４−カ
ルボキサミド
１．５−ジメチ／ｌ／−８−フルオロ−Ｎ−（２−メチ
ル−８−イソプロポキシフェニ／Ｌ／）ピラゾール−４
−カルボキサミド
５−クロロ−１−メチ／Ｌ／８−トリフルオロメチル−
Ｎ−（２−メチ）ｖ−８−イソプロボキシフェニ／Ｌ／
）ピフゾー／Ｌ’−４−カμボキサミド５−フルオロ−
１−メチ／ｌ／−８−トリフルオロメチル−Ｎ−（２−
メチｆｉ／−３−イソプロポキシフェニル）ピッジー／
ｌ／−４−カルボキサミド
３．５−ジクロロ−１−メチル−Ｎ−（２−メチル−８
−イソブロポキシフェニ／Ｉ／）ピッゾール−４−カル
ホキサミド
３．５−ジフルオロ−１−メチル−Ｎ−（２−メチル−
８−イソプロポキシフェニ／ｌ／）ピラシー／ｌ／−４
−カルボキサミド
本発明化合物は例えば一般式
と同じ意味を表わす０）で示される基を表わし、Ｘはハ
ロゲン原子を表わす０〕
で示されるカルボン酸ハライドと２−メチ／Ｉ’−８−
イソプロポキシアニリンとを反応させることによって製
造するととができるＯ
仁の場合、２−メチ／Ｉ／−８−イソプロポキシアニリ
ン１当量に適当な溶媒、たとえばベンゼン、トルエン、
キシレン等の炭化水素、クロロベンゼン、塩化メチレン
、クロロホルム、四塩化ｔ＃素等のハロゲン化度化水素
類、ジイソプロヒルエーテル、テトラヒドロフラン、ジ
オキサン等のエーテ／Ｌ／類、アセトン、メチルエチル
ケトン等のケトン類、酢酸エチ／Ｌ−′等ノエステル類
、アセトニトリル等のニドυμ類、ジメチルヌルホキシ
ト、ジメチルホルムアミド、水等を加よるかまたは無溶
媒で、通常０．４〜１．６当量、好ましくは０，５〜１
．１当量の一般式■で示されるカルボン酸ハフイドを反
応させる。2-Methyl-N-(2-methyl-8-isoproxyphenyl)furan-8-carboxamide 2-trifluoromethi p-N-(2-methyμm8-isopropoxyphenyl/I/)furan-8- Carboxamide 2.5-dimethyl-N-(2-methy/L'-8-isobupboxyphenyl/)furan-8-carboxamide 5-methyl-2-trifluoromethyl-N-(2-methyA/-8 -isoproboquinpheni/L/)furan-8-
Carboxamide 2-methyl-N-(2-methy/L'-8-isoproboxypheniA/)thiophene-8-carboxamide 2-trifluoromethyl-N-(2-methyl-8-isoproboxypheni/I/ ) Thiophene-8-carboxamide 2,5-dimethymu-N-(2-methyl-8-isobroboxyVphenyl)thiophene-8-carboxamide 5-methyl-2-trifluoromethyl-N-(2-methyllL /-8-isopropoxyphenylene/L/)thiophene-8-carboxamide 8-methyl-N-(2-methy/L/-8-isopropoxypheniμ)thiophene-2-carboxamide 8-trifluoromethyl-N -(2-Methyl-8-isoproboxyphenyleneμ)thiophene-8-forceμboxamide 8.5-dimethyl-N-(2-methy/I/-8-isoproboxyphenylene/L/)thiophene-2 -carboxamide 5-methyv-8-)lifluoromethyl-N=(2-methy/l/-8-isobropoxypheny/I/)thiophene-2-carboxamide 1,8-dimethyyv-N-(2- Methi/I/-8-isopropoxyphenylene/I/) bikuzo/L'-4-carboxamide 1,5-dimethyμ-N-(2-methy/L'-8-isopropoxyphenylene/L/) piracy/ L/-4-ruboxamide 1-methy/L'-8-)lifluoromethyl-'N-
(2-methyA/-8-isopropoxyphenylene/I/)pidgey/l/-4-carboxamide 1-methy/L'-5-)lifluoromethyl-N-(2-
Methyl/I/-8-isopropoxyphenylene/L/)pidgey/l/-4-carboxamide 1.8.5-)limethyl-N-(2-methyl-8-isopropoxyphenylene/l/)pyrazole-4 -caμboxamide 1,8-dimethy1v-5-)lifluoromethyl-N-(
2-Methyl-8-isoproboxyphenylene/L/)piracy/L'-4-carboxamide 1,5-dimethyl-8-
Trifluoromethyl-N-(2-methy/I/-8-isopropoxypheniμ)hiracy/l/-4-carboxamide 5-chloro-1,8-dimethyμ-N-(2-methy1
v-8-isopropoxyphenyl) pidgey/l/-4
-carboxamide 1,8-dimethyA/-5-fluoro-N -(2-methy)v-3-isoproboxypheny/l/)pidgey/l
/-4-carboxamide 3-chloro-1,5-dimethyl-N-(2-methy1v-
B-isopropoquinphenyl)pidgey/L'-4-carboxamide 1,5-dimethy/l/-8-fluoro-N-(2-methyl-8-isopropoxypheny/L/)pyrazole-4
-Carboxamide 5-chloro-1-methy/L/8-trifluoromethyl-
N-(2-methy)v-8-isoproboxypheny/L/
) pifzo/L'-4-caμboxamide 5-fluoro-
1-Methyl/l/-8-trifluoromethyl-N-(2-
methifi/-3-isopropoxyphenyl)pidgey/
l/-4-carboxamide 3,5-dichloro-1-methyl-N-(2-methyl-8
-isobropoxyphenylene/I/) pizzol-4-carfoxamide 3,5-difluoro-1-methyl-N-(2-methyl-
8-isopropoxyphenylene/l/) piracy/l/-4
-Carboxamide The compound of the present invention represents, for example, a group represented by 0) which has the same meaning as the general formula, and X represents a halogen atom.
In the case of O, which can be prepared by reacting with isopropoxyaniline, one equivalent of 2-methy/I/-8-isopropoxyaniline is mixed with a suitable solvent such as benzene, toluene,
Hydrocarbons such as xylene, halogenated hydrogen dihydrides such as chlorobenzene, methylene chloride, chloroform, and tetrachloride, ethers/L/s such as diisopropyl ether, tetrahydrofuran, and dioxane, and ketones such as acetone and methyl ethyl ketone. , esters such as ethyl acetate/L-', nitrides such as acetonitrile, dimethylnulphoxide, dimethylformamide, water, etc., or without a solvent, usually 0.4 to 1.6 equivalents, preferably 0. ,5~1
．． One equivalent of a carboxylic acid hafide represented by the general formula (2) is reacted.
マタ、一般式叩で示されるカルボン酸ハフイドに上記溶
媒類を加えるかあるいは無溶媒で２−メチ／ｌ／８−イ
ソプロポキンアニリンを加えて反応させるととも可能で
ある〇
反応は溶媒の没固点から沸点までの任意の温度、好まし
くは０℃から溶媒の沸点までの温度で行なうととができ
、必要に応じては加熱あるいは冷却することができる〇
使用する一般式叩で示されるカルボン酸ハライドとして
は、カルボン酸クロライド、力μボン酸フルオライド、
カルボン酸ブロマイド等をあげるととができる〇
さらに該反応には、脱酸剤として水酸化ナトリウム、水
酸化カリウム、トリエチルアミン、Ｎ−メチルモルホリ
ン、トリエチルアミン、ビリジン等を使用することがで
きる。It is possible to react by adding the above solvents to the carboxylic acid hafide represented by the general formula, or by adding 2-methy/l/8-isopropoquine aniline without a solvent.〇The reaction is caused by solidification of the solvent. The reaction can be carried out at any temperature from 0°C to the boiling point, preferably from 0°C to the boiling point of the solvent, and can be heated or cooled as necessary. Carboxylic acid represented by the general formula used Examples of halides include carboxylic acid chloride, μboxylic acid fluoride,
Carboxylic acid bromide and the like can be used. Furthermore, in the reaction, sodium hydroxide, potassium hydroxide, triethylamine, N-methylmorpholine, triethylamine, pyridine, etc. can be used as a deoxidizing agent.
これらの脱酸剤は通常触媒量から２当量の範囲で使用さ
れるが、好ましくは０．９５〜１．１当量で反応を行な
うことができる。These deoxidizing agents are usually used in an amount ranging from a catalytic amount to 2 equivalents, but preferably 0.95 to 1.1 equivalents can carry out the reaction.
上記のような製造法によシ得られた本発明化合物は、必
要に応じて再結晶あるいはカラムクロマトグラフィーに
よって精製することもできるＯ
〈実施例〉
以下、本発明を製造例、製剤例および試験例によりさら
に詳しく説明する。The compound of the present invention obtained by the above production method can be purified by recrystallization or column chromatography if necessary. This will be explained in more detail using an example.
〈製造例〉
２−メチ／Ｉ／−８−イソプロポキンアニリン６６０ｍ
Ｆおよびピリジン２ｍｌのトルエン１０ｍｊ溶液に室温
で攪拌しつつ、２−）！ｊフルオロメチルベンゾイルク
ロリド８８４ｍＦのトルエン５ｍＪ溶液を流加し、その
後室温で１２時間攪拌した。次に、反応溶液を冷水に注
入し、分液した後、水層を酢酸エチルで抽出した０得ら
れた有機層と酢酸エチル層を混合し無水硫酸マグネシウ
ムで乾燥した後溶媒を減圧留去した◎残査をトルエン／
ｎ−ヘキサン混合溶媒を用いて再Ｍ晶Ｌ、２−）リフル
オロメチル−Ｎ−（２−メチＡ／−３−イソプロポキシ
フェニ）Ｖ）ベンズアミド１．０５Ｆを得たＯ
ｍｐ、 １５２．４℃
このような製造法によって得られる本発明化合物の代表
的なもののいくつかを第１表に示す。<Production example> 2-methy/I/-8-isopropoquine aniline 660m
F and 2 ml of pyridine in 10 mj of toluene solution while stirring at room temperature, 2-)! A solution of 884 mF of fluoromethylbenzoyl chloride in 5 mJ of toluene was added, and then stirred at room temperature for 12 hours. Next, the reaction solution was poured into cold water and separated, and the aqueous layer was extracted with ethyl acetate. The obtained organic layer and ethyl acetate layer were mixed, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. ◎Residue to toluene/
Re-M crystal L, 2-)lifluoromethyl-N-(2-methyA/-3-isopropoxyphenylene)V)benzamide 1.05F was obtained using n-hexane mixed solvent O mp, 152.4 Table 1 shows some typical compounds of the present invention obtained by such a production method.
第 １ 表
で示される本発明化合物
次に製剤例を示す。なお、本発明化合物は第１表の化合
物番号で示す。部は重量部である。Formulation examples of the compounds of the present invention shown in Table 1 are shown below. The compounds of the present invention are indicated by compound numbers in Table 1. Parts are parts by weight.
製剤例１
本発明化合物（１１〜０ηの各々ｆｉ ０部、リグニン
ヌルホン酸カルシウム８部、ツウリフに／硫酸ナトリウ
ム２部および合成含水酸化珪素４５部をよく粉砕混合し
て水利剤を得る。Formulation Example 1 A water conservancy is obtained by thoroughly pulverizing and mixing 0 part of each of the compounds of the present invention (fi of 11 to 0η), 8 parts of calcium lignin sulfonate, 2 parts of sodium sulfuric acid/sulfate, and 45 parts of synthetic hydrous silicon oxide.
製剤例２
本発明化合物（１）〜（ＩＩ）の各々１部部、ポリオキ
シエチレンスチリンフェニルエーテＡ／ １４ 部、＝
ドデシルベンゼンスルホン酸カルシウム６部、キＶレン
７０部をよく混合して乳剤を得る０製剤例８
本発明化合物（１）〜０１）の各々２部、合成含水酸化
珪素１部、リグニンスルホン酸カルシウム２部、ベント
ナイト８０部およびカオリンクレー６５部をよく粉砕混
合し、水を加えてよく練り合せた後、造粒乾燥して粒剤
を得る０
製剤例４
本発明化合物（１）〜（１１）の各々２５部、ポリオキ
Ｖエチレンソルビタンモノオレエート８部、０Ｍ０８部
、水６９部を混合し、粒度が５ミクロン以下になるまて
湿式粉砕して懸濁剤を得る〇製剤例５
本発明化合物（１）〜０１）の各々２部、カオリンクレ
ー８８部およびタルク１０部をよく粉砕混合して粉剤を
得る０
次に本発明化合物が殺菌剤の有効成分として有用である
ことを試験例で示す。力お、本発明化合物は、第１表の
化合物番号で示し、比較対照に用いた化合物は第２表の
化合物記号で示す。Formulation Example 2 1 part each of the compounds (1) to (II) of the present invention, 14 parts of polyoxyethylene styrine phenyl ether A/=
Formulation Example 8: 6 parts of calcium dodecylbenzenesulfonate and 70 parts of dichloromethane are thoroughly mixed to obtain an emulsion. 2 parts each of the compounds (1) to 01) of the present invention, 1 part of synthetic hydrous silicon oxide, and calcium ligninsulfonate. 2 parts of bentonite, 80 parts of bentonite, and 65 parts of kaolin clay are thoroughly ground and mixed, water is added, and the mixture is thoroughly kneaded, followed by granulation and drying to obtain granules. Formulation Example 4 Present Compounds (1) to (11) 25 parts of each of the above, 8 parts of polyoxy V ethylene sorbitan monooleate, 8 parts of 0M0, and 69 parts of water are mixed and wet-pulverized until the particle size becomes 5 microns or less to obtain a suspension. Formulation Example 5 Compound of the Invention 2 parts of each of (1) to 01), 88 parts of kaolin clay, and 10 parts of talc are thoroughly ground and mixed to obtain a powder. Next, test examples will show that the compound of the present invention is useful as an active ingredient of a fungicide. . Compounds of the present invention are indicated by compound numbers in Table 1, and compounds used for comparison are indicated by compound symbols in Table 2.
第 ２ 表
試験例１ イネ紋枯病予防効果試験
プラスチックポットに砂埃上を詰め、イネ（近畿８８号
）を播種し、温室内で６０日間育成した０６〜７葉が展
開したイネの幼苗に、製剤例２に準じて乳剤にした供試
化合物を、水で希釈して所定濃度にし、それを葉面に充
分付着するように茎葉散布した。散布４時間後、イネ紋
枯病菌の含冒寒天片を貼付接種した０接種後２８℃、多
湿下で４日間育成し、防除効力を調査した。Table 2 Test Example 1 Preventive effect test on rice sheath blight A plastic pot was filled with dust, rice (Kinki No. 88) was sown and grown in a greenhouse for 60 days. A test compound made into an emulsion according to Formulation Example 2 was diluted with water to a predetermined concentration, and was sprayed on foliage so that it would sufficiently adhere to the leaf surface. Four hours after the spraying, agar pieces impregnated with the rice sheath blight fungus were pasted and inoculated. After 0 inoculation, the plants were grown for 4 days at 28° C. under humid conditions, and their control efficacy was investigated.
その結果を第８表に示す。The results are shown in Table 8.
尚、防除効力は、調査時の供試植物の発病状態すなわち
葉、茎等の菌詐、病斑の程度を肉眼観察し、菌叢、病斑
が全く認められなければｌ」、１０部程度認められれば
「４」、ａＯ＊程度認められればｒ８Ｊ、５０部６程度
認められればｒＬＩ、７０部程度認められれば「１」、
それ以上で化合物を供試していない場合の発病状態と差
が認められなければ印」として、θ〜５の６段階に評価
し、０．１．２．８．４．６で示す。In addition, the control efficacy is determined by visually observing the disease state of the test plants at the time of investigation, that is, the extent of bacterial flora and lesions on leaves, stems, etc., and if no bacterial flora or lesions are observed at all, approximately 10 parts. ``4'' if approved, r8J if approx.
If there is no difference from the disease onset state in the case where no compound is tested, it is marked as ``marked'' and evaluated on a 6-level scale of θ to 5, and indicated as 0.1.2.8.4.6.
第 ８ 表
試験例２ イネ紋枯病浸透移行効果試験１８０ｍＪ容の
プラスチックポットに砂壌土を詰め、イネ（近畿８８号
）を播種し、温室内で８週間育成した。６〜７葉が展開
したイネに、製剤例２に準じて乳剤にした供試化合物を
水で希釈し、その所定量を土壊に潅注した０潅注後７日
間温室内で育成し、イネ紋枯病菌の食菌寒天片を貼付接
種した０接種後２８℃、多湿下で４日間育成し、防除力
を調査した。Table 8 Test Example 2 Rice sheath blight penetration and transfer effect test A 180 mJ capacity plastic pot was filled with sandy loam, and rice (Kinki No. 88) was sown and grown in a greenhouse for 8 weeks. A test compound prepared as an emulsion according to Formulation Example 2 was diluted with water on a rice plant with 6 to 7 leaves developed, and a predetermined amount of it was irrigated into the soil.After irrigation, the rice was grown in a greenhouse for 7 days, and the rice pattern was After 0 inoculation, the plants were grown for 4 days at 28° C. under humid conditions, and their control ability was investigated.
結果を第４表に示す〇
第 ４ 表
試験例８ コムギ赤さび病治療効果試験プラスチックポ
ットに砂壌土を詰め、コムギ（農林７８号）を播種し、
温室内で１０日間育成した０第２〜８葉が展開したコム
ギの幼苗に、コムギ赤さび病菌を散粉接種した０接種後
２８℃、多湿下で１日育成し、製剤例１に準じて水利剤
にした供試化合物を水で希釈して所定濃度にし、それを
葉面に充分付着するように茎葉散布した０散布後２８℃
照明下で７日間育成し、防除効力を調査した〇
結果を第５表に示す。The results are shown in Table 4 Table 4 Test Example 8 Wheat Rust Treatment Efficacy Test A plastic pot was filled with sandy loam and wheat (Norin No. 78) was sown.
Wheat seedlings grown in a greenhouse for 10 days and with 2nd to 8th leaves developed were dust inoculated with wheat rust fungus. After inoculation, the seedlings were grown for 1 day at 28°C and under high humidity, and an irrigation agent was prepared according to Formulation Example 1. The test compound was diluted with water to a predetermined concentration, and sprayed on the foliage to ensure sufficient adhesion to the leaf surface.After spraying at 28°C.
Table 5 shows the results of cultivating under lighting for 7 days and investigating the pesticidal efficacy.
＼８、
第 ５ 表
〈発明の効果〉
本発明化合物は、種々の植物病原菌、特に担子菌類に属
する微生物による植物病害に対して卓効を示すことから
、殺菌剤の有効成分として種々の用途に用いることがで
きる。\8, Table 5 <Effects of the Invention> The compounds of the present invention are highly effective against plant diseases caused by various plant pathogenic bacteria, especially microorganisms belonging to the Basidiomycetes, and therefore can be used in various applications as active ingredients of fungicides. Can be used.
（２７完）(27 completed)
Claims (1)
、▲数式、化学式、表等があります▼ または▲数式、化学式、表等があります▼ （ここでＲ＾１およびＲ＾２は同一または相異なり水素
原子、ハロゲン原子、メチル基または トリフルオロメチル基を表わす。）で示さ れる基を表わす。〕 で示されるアニリド誘導体。 （２）上記一般式で示されるアニリド誘導体において、
Ｒが一般式▲数式、化学式、表等があります▼、▲数式
、化学式、表等があります▼または ▲数式、化学式、表等があります▼で示される基である
特許請求の範囲 第１項記載のアニリド誘導体。 （８）一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｒは一般式▲数式、化学式、表等があります▼
、▲数式、化学式、表等があります▼ または▲数式、化学式、表等があります▼ （ここでＲ＾１およびＲ＾２は同一または相異なり水素
原子、ハロゲン原子、メチル基または トリフルオロメチル基を表わす。）で示さ れる基を表わす。〕 で示されるアニリド誘導体を有効成分として含有するこ
とを特徴とする殺菌剤。 （４）上記一般式で示されるアニリド誘導体においてＲ
が式▲数式、化学式、表等があります▼、▲数式、化学
式、表等があります▼または ▲数式、化学式、表等があります▼で示される基である
特許請求の範囲 第８項記載の殺菌剤。[Claims] (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R is a general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (Here, R^1 and R^2 are the same or different and are hydrogen atoms, halogen atoms, methyl groups, or trifluoromethyl represents a group represented by ). ] Anilide derivative represented by. (2) In the anilide derivative represented by the above general formula,
Claim 1 states that R is a group represented by the general formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Anilide derivative of. (8) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R is the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (Here, R^1 and R^2 are the same or different and are hydrogen atoms, halogen atoms, methyl groups, or trifluoromethyl represents a group represented by ). ] A disinfectant characterized by containing an anilide derivative represented by the following as an active ingredient. (4) In the anilide derivative represented by the above general formula, R
is a group represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ The sterilization according to claim 8 agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9259286A JPS62249975A (en) | 1986-04-22 | 1986-04-22 | Anilide derivative and germicide containing said derivative as active ingredient |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9259286A JPS62249975A (en) | 1986-04-22 | 1986-04-22 | Anilide derivative and germicide containing said derivative as active ingredient |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62249975A true JPS62249975A (en) | 1987-10-30 |
Family
ID=14058715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9259286A Pending JPS62249975A (en) | 1986-04-22 | 1986-04-22 | Anilide derivative and germicide containing said derivative as active ingredient |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62249975A (en) |
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| US5223526A (en) * | 1991-12-06 | 1993-06-29 | Monsanto Company | Pyrazole carboxanilide fungicides and use |
| WO1996038419A1 (en) * | 1995-05-31 | 1996-12-05 | Nissan Chemical Industries, Ltd. | 5-pyrazolecarboxamide derivatives and plant disease control agent |
| WO2003010149A1 (en) * | 2001-07-25 | 2003-02-06 | Bayer Cropscience Ag | Pyrazolylcarboxanilides as fungicides |
| JP2006518345A (en) * | 2003-01-29 | 2006-08-10 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | Pyrazolylcarboxyanilides for controlling undesirable microorganisms |
| US7501530B2 (en) | 2003-03-24 | 2009-03-10 | Basf Aktiengesellschaft | Trifluoromethyl-thiophene carboxylic acid aniledes and use thereof as fungicides |
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| WO2011142009A1 (en) * | 2010-05-12 | 2011-11-17 | 株式会社エス・ディー・エス バイオテック | Preservative for preserving wood and method for treating wood |
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1986
- 1986-04-22 JP JP9259286A patent/JPS62249975A/en active Pending
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| WO1996038419A1 (en) * | 1995-05-31 | 1996-12-05 | Nissan Chemical Industries, Ltd. | 5-pyrazolecarboxamide derivatives and plant disease control agent |
| WO2003010149A1 (en) * | 2001-07-25 | 2003-02-06 | Bayer Cropscience Ag | Pyrazolylcarboxanilides as fungicides |
| JP2005501044A (en) * | 2001-07-25 | 2005-01-13 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | Pyrazolylcarboxanilide as a fungicide |
| US7538073B2 (en) | 2001-07-25 | 2009-05-26 | Bayer Cropscience Ag | Pyrazoylcarboxanilides as fungicides |
| JP2010195800A (en) * | 2001-07-25 | 2010-09-09 | Bayer Cropscience Ag | Pyrazolylcarboxanilide as sterilizer |
| JP2013136581A (en) * | 2001-07-25 | 2013-07-11 | Bayer Cropscience Ag | Pyrazolylcarboxanilide as fungicide |
| JP2006518345A (en) * | 2003-01-29 | 2006-08-10 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | Pyrazolylcarboxyanilides for controlling undesirable microorganisms |
| US7501530B2 (en) | 2003-03-24 | 2009-03-10 | Basf Aktiengesellschaft | Trifluoromethyl-thiophene carboxylic acid aniledes and use thereof as fungicides |
| JP2010150186A (en) * | 2008-12-25 | 2010-07-08 | Sds Biotech Corp | Wood preservation antiseptic and wood treating method |
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| CN108059613B (en) * | 2016-11-09 | 2020-09-25 | 沈阳中化农药化工研发有限公司 | Pyrazole amide compound and application thereof |
| CN109548787A (en) * | 2018-10-20 | 2019-04-02 | 南通江山农药化工股份有限公司 | A kind of bactericidal composition and its application |
| CN111285807A (en) * | 2018-12-07 | 2020-06-16 | 沈阳中化农药化工研发有限公司 | Pyrazole amide compound and application thereof |
| CN111285807B (en) * | 2018-12-07 | 2023-06-23 | 沈阳中化农药化工研发有限公司 | Pyrazole amide compound and application thereof |
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