WO2002034049A1 - Compositions microbicides utilisees dans le domaine agricole et horticole et contenant des derives de sulfonanilide - Google Patents

Compositions microbicides utilisees dans le domaine agricole et horticole et contenant des derives de sulfonanilide Download PDF

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Publication number
WO2002034049A1
WO2002034049A1 PCT/JP2001/009178 JP0109178W WO0234049A1 WO 2002034049 A1 WO2002034049 A1 WO 2002034049A1 JP 0109178 W JP0109178 W JP 0109178W WO 0234049 A1 WO0234049 A1 WO 0234049A1
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group
agricultural
horticultural use
use according
microbicidal composition
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PCT/JP2001/009178
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English (en)
Japanese (ja)
Inventor
Takanori Tabuchi
Ryo Ishikawa
Tetsuhiro Yamamoto
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Sumitomo Chemical Takeda Agro Company, Limited
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Priority to AU2001295972A priority Critical patent/AU2001295972A1/en
Publication of WO2002034049A1 publication Critical patent/WO2002034049A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides

Definitions

  • the present invention relates to a microbicidal composition for agricultural and horticultural use containing a sulfonulylide derivative.
  • JP-B-47-15119 JP-A-56-20564, JP-A-57-31655, JP-A-58-118558, JP-A-58-219159, JP-A-61-197553, JP-A-61-200959, JP-A-61-200960, JP-A-61-205247, JP-A-61-205248, JP-A-61-257960, JP-A-61-271270, JP-A-61-271270 62-190104, JP-A-63-270658, JP-A-11-156953, JP-A-11-272566, JP-A-2-72151, JP-A-2-96560, JP-A-2-212467, JP-A-2-231465, U.S.
  • penzinoles sulfonides and styrene sulfonides as microbicidal compositions for agricultural and horticultural use.
  • Compounds having a haloalkyl group, a cyano group, or a thiocarbamoyl group at the onoleto position of the benzene ring on the phosphorous side are those having a benzenesnolephoeno W rule of 41-triphnoleo-methinolebenzenes / lefonyl, 3,5- It has not been reported except for compounds which are disubstituted benzenesulfonyl.
  • An object of the present invention is to provide an agricultural and horticultural microbicidal composition containing a sulfonanilide derivative, which has a small effect on human animals, natural enemies, the environment, fishes and crops, is safe and has an excellent control effect on resistant microorganisms.
  • the present inventors have conducted intensive studies for many years in order to find a compound having an excellent microbicidal activity, and as a result, have found that a sulfonyllide derivative having a specific structure or a salt thereof Surprisingly have a very strong microbicidal action and It has been found to have little impact on livestock, natural enemies, the environment, fish and crops and is safe.
  • the present invention has been completed.
  • the present inventors have conducted intensive studies for many years to find a compound having excellent microbicidal activity in order to solve the above-mentioned problems, and as a result, surprisingly, a sulfonuride derivative having a specific structure or a salt thereof was unexpectedly obtained.
  • the present invention has been completed. That is, the present invention
  • X 1, X 2, X 3 and X 4 are each independently a hydrogen atom, an alkyl group, ⁇ preparative 3 alkoxy group, a halogen atom or Shiano group, Y ⁇ DOO 3 Haroa alkyl group, Chio a carbamoyl group, Shiano group or a nitro group, Z is ⁇ 3 ⁇ .
  • a microbial biocidal composition for agricultural and horticultural use containing the sulfonanilide derivative (I) or a salt thereof as an active ingredient;
  • Z is a halogen atom, methylthio group, cyano group or -toro group, and m is one or more.
  • microbicidal composition for agricultural and horticultural use according to the above (6), wherein Z is a halogen atom, a methylthio group, a cyano group or a nitro group, and m is 1 or 2.
  • the present invention provides the microbicidal composition for agricultural and horticultural use according to any one of the above (1) to (15), which is used for disinfecting clubroot fungi or Aphanomyces spp. On cruciferous crops.
  • the sulfonanilide derivative (I) may have optically active, diastereomeric and / or geometric isomers.
  • the present invention includes each of these isomers and a mixture of these isomers.
  • examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • haloalkyl group for Y examples include, for example, fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, chlorofluoromethyl group, bromofluoromethyl group, chlorodifluoromethyl group, Nore, trichloromethyl, tribromomethinole,
  • 2,2,2-Trifnoroleochinole group 2,2,2-Trichloromethyl group, 1,1,2,2-tetrafluoroethyl group, Pentafluoroethyl group, 2,2 , 2-trifluoro-11- (trifluoromethyl) ethyl group, heptafluoropropyl group and the like. ⁇
  • Examples thereof include a methoxy group, an ethoxy group, a propoxy group, and an isopropoxy group.
  • A is preferably a chemical bond, and X 1 and X 4 are preferably hydrogen atoms.
  • X 2 and X 3 are preferably a hydrogen atom or a —3 alkyl group, particularly preferably a hydrogen atom, a methyl group or an ethyl group.
  • Y is preferably a cyano group or a nitro group, particularly preferably a nitro group.
  • the salt of the sulfonide derivative (I) may be any salt acceptable in agrochemical chemistry.
  • the sulfonide derivative (I) has basic properties, for example, salts of inorganic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, nitric acid, perchloric acid, etc. ,
  • inorganic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, nitric acid, perchloric acid, etc.
  • acetic acid, propionic acid tartaric acid, malic acid, citric acid
  • Salts of organic acids such as acid, succinic acid, benzoic acid, picric acid, methanesulfonic acid, p-toluenesulfonic acid and the like can be mentioned.
  • the sulfonanilide derivative (I) has an acidic property, for example, an alkali metal salt such as lithium, sodium, and potassium; an alkaline earth metal salt such as magnesium and calcium; for example, iron, copper, zinc, and manganese; Heavy metal salts such as ammonia, methylamine, dimethylamine, trimethylamine, triethynoleamine, ethylenediamine, TME DA (tetramethylethylenediamine), aniline, N, N-dimethyl / leaniline, pyridin, lutidine, Examples thereof include ammonium salts such as collidine and hydrazine, for example, salts with urea, guanine and the like.
  • an alkali metal salt such as lithium, sodium, and potassium
  • an alkaline earth metal salt such as magnesium and calcium
  • iron, copper, zinc, and manganese Heavy metal salts such as ammonia, methylamine, dimethylamine, trimethylamine, triethynoleamine, ethylened
  • an active ingredient is mixed or dispersed with an appropriate liquid carrier, or mixed or adsorbed with an appropriate solid carrier depending on the purpose of use, as an emulsion, oil, aqueous suspension, Emulsion, liquid, ULV, wettable powder, powder, DL (driftless) powder, granule, fine granule, fine granule F, flowable, drive mouth abs, tablet, jumbo, spray, ointment, paste, Used as a form for foams, aerosols, microforces, seed coatings, smokers, and sticks for plant irrigation.
  • preparations may be used, if necessary, for example, emulsifiers, suspending agents, spreading agents, penetrants, wetting agents, dispersants, mucilage agents, stabilizers, binders, flow aids, anti-caking agents, flocculants, oxidants Inhibitors, suspending agents, antifoaming agents, antifreezing agents, preservatives, moisture removers, ultraviolet absorbers, ultraviolet scattering agents, coloring agents, suspension stabilizers, etc. may be added, prepared in a manner known per se can do.
  • an emulsion can be produced by uniformly mixing and dissolving a sulfonanilide derivative (I) or a salt thereof, an emulsifier, an organic solvent and the like.
  • granules, wettable powders can be produced by uniformly mixing and granulating a sulfonanilide derivative (I) or a salt thereof, a dispersant (surfactant), a binder, a bulking agent (or a solid carrier), and the like.
  • powders, DL powders and the like can be produced by uniformly mixing and pulverizing a snorehon-lide derivative (I) or a salt thereof, a bulking agent (or a solid carrier) and the like.
  • a flowable agent is produced by mixing and dispersing components such as a sulfonanilide derivative (I) or a salt thereof and a dispersant using a stirrer, and wet-milling using a dyno mill or the like.
  • a jumbo agent can be produced by uniformly mixing and granulating a sulfonamide derivative (I) or a salt thereof, a dispersant (surfactant), a binder, a suspending agent, a bulking agent (or a solid carrier), and the like. . '
  • Jumbo powders, powders, granules, wettable powders, wettable powders, etc. may be packaged in water-soluble films in 20 to 200 g units for easy application.
  • the water-soluble film include polyvinyl alcohol, carboxymethylcellose, starch, gelatin, polypyrrolidone, polyacrylic acid and salts thereof, and pullulan (trade name, sold by Hayashibara Co., Ltd.).
  • starch-based polysaccharides, and thermoplastic water-soluble polymers such as Paogen (trade name, sold by Dai-ichi Kogyo Seiyaku Co., Ltd.).
  • liquid carrier examples include water, methanol, ethanol, propanol, isopropanol, alcohols such as ethylene glycol, etc., ketones such as acetone, methyl ethyl ketone, etc., for example, 1,4-dioxane, tetrahydrofuran Ethers such as ethylene glycolone monomethyl ether and propylene glycol monomethyl ether; ethylene hydrocarbons such as kerosene, kerosene, fuel oil, machine oils, and edible oils such as benzene and toluene , Xylene, solvent naphtha, methylnaphthalene, etc., aromatic hydrocarbons, such as dichloromethane, chloroform, carbon tetrachloride, etc., halogenated hydrocarbons, such as N, N-dimethylformamide, N, N-dimethyl Solvents such as acid amides such as acetamide, for example, esters such as
  • solid carriers include vegetable powders such as soybean flour, tobacco flour, flour, and wood flour; clays such as kaolin, bentonite, and acid clay; Talcs, for example, mineral powders such as silicas such as diatomaceous earth and mica powder, calcium carbonate, alumina, sulfur powders, activated carbon and the like are used, and one or more (preferably one to three) of these are suitably used. It can be used as appropriate by mixing in proportions.
  • ointment bases include, for example, polyethylene glycol, polyethylene, polyhydric alcohol esters of higher fatty acids such as glyceryl monostearate, cellulose derivatives such as methylcellulose, sodium alginate, bentonite, higher alcohols, such as glycerin
  • polyhydric alcohols such as petrolatum, petrolatum, white petrolatum, liquid paraffin, lard, various vegetable oils, lanolin, dehydrated lanolin, hardened oil, resins, etc. (preferably:!: ⁇ 3 types).
  • surfactants shown below to the above or the like are appropriately used.
  • 'Surfactants used as emulsifiers, spreading agents, penetrants, and dispersants include, as necessary' stones, polyoxyethylene alkylaryl ethers [e.g., Neugen
  • TM (TM indicates that it is a registered trademark), 'A 142 (E ⁇ A142) TM; Daiichi Kogyo Seiyaku Co., Ltd., Nonal ⁇ ; Toho Chemical Co., Ltd.] , 'Alkyl sulfates [eg, Emar 10 TM , Emar 40 TM ; manufactured by Kao Corporation], alkyl sulfonates [eg, neogen, Neogen T TM ; manufactured by Daiichi Kogyo Seiyaku Co., Ltd., Neopellets box; manufactured by Kao Corporation], polyethylene glycol ethers [e.g., Nonipol 8 5 TM, Nonipol 1 0 0 TM, Nonipol 1 6 0 TM; Sanyo Kasei Co., Ltd.], Okaa Le call esters [e.g., Nonionic and anionic surfactants such as Tween 20 TM and Tween 80 TM ; manufactured by Kao Corporation].
  • an insecticide an acaricide, a nematicide, a plant hormone, a plant growth regulator, a fungicide, a synergist, an attractant, a repellent, a pigment, a fertilizer.
  • an insecticide an acaricide, a nematicide, a plant hormone, a plant growth regulator, a fungicide, a synergist, an attractant, a repellent, a pigment, a fertilizer.
  • the present invention includes an agricultural and horticultural microbicide containing the sulfonanilide derivative (I) or a salt thereof and another pesticidal active ingredient.
  • Other pesticide active ingredients It may be contained in the same preparation as the sulfonide derivative (I) or a salt thereof. Alternatively, they may be mixed at the time of use after being formulated into separate formulations. Representative examples of insecticides, acaricides, and nematicides that can be used by mixing with the sulfonanilide derivative (I) or a salt thereof are shown below.
  • Asefeto (a Ce phate), Asetamipu di K cetamiprid), Akurina Bok Jin (acrinathrin), Aranikanorebu (alanycarb), aldrin (aldrin), allethrin (allethrin), aluminum phosphide (Aluminum phosphide) amino Torazu (amitraz), arsenite Acid (Arsenic acid), avermectin '(avermectin-B), Benyaku, becaniolev, benfracanoleb
  • PAP phenthoate: PAP
  • hosalon phosalone
  • phosmet phosmet: PMP
  • pirimicarb piriraicarb
  • pirimiphos Methinole piriraiphos-methyl
  • potassium oleate Potassium oleate
  • profenofos propaphos
  • Tef lubenzuron Tefunore Bok phosphorus (tefluth: rin), temephos (temephos), Te Bok easier Ronorebinhosu (tetrachlorvinphos), tetradifon (tetradifon), Chiakuropuri de (thiacloprid), Chiame Tokisamu (thiamethoxatn), Chioshikuramu (thiocyclara), Chiojikanorebu (Thiodicarb), thiometon, tolfenpyrad
  • fluazinara fluazinara
  • fluodioxonil fludioxonil
  • flunoremetoba flumetover
  • flunolenoreimide fluoroimide
  • funolequin conazo mono fluquinconazole
  • funoresnolefamide f lusatn
  • prochloraz procymidone
  • the diseases controlled by the sulfonanilide derivative (I) or its salt are: For example, blast (Pyricularia oryzae), sesame leaf blight +
  • Wheat diseases such as (Septoria tritici) and naked smut (Ustilago tritici), for example, maize diseases such as seedling blight (Pythium debaryanum), for example, red snow rot
  • Uromyces fabae, Uromyces 'phaseoli Broad bean diseases such as Botrytis cinerea', Endo diseases such as root rot (Aphanomyces euteiches), and laccasei such as brown spot (Mycosphaerella arachidicola) Diseases, for example, cabbage diseases such as seedling wilt (Rhizoctonia solani), such as powdery mildew (Sphaerotheca fuliginea), vine disease
  • the agricultural and horticultural microbicide containing the sulfonanilide derivative (I) or a salt thereof of the present invention as an active ingredient can be used in the same manner as a conventional microbicide.
  • it can be used for nursery box treatment, crop foliage application, post-transplant irrigation treatment, crop plant treatment, paddy water application, seed treatment or soil mixing treatment, direct application to fruit tree trunks, etc.
  • it is particularly preferable to use a soil mixing treatment, a nursery box treatment or a treatment at the time of irrigation after transplantation.
  • the amount of application can be varied over a wide range according to the time of application, the place of application, the method of application, etc.
  • the amount of active ingredient (sulfoneuride derivative (I) or its salt) per hectare is zero. 3 g ⁇ : LO, 00 g, preferably 50 g ⁇ 5, It is desirable that the application be made to be 0 0 g.
  • the composition of the present invention is a wettable powder
  • the composition is diluted so that the final concentration of the active ingredient is in the range of 0.1 to 10 ppm, preferably 10 to 10 ppm. And use it.
  • the content of the sulfonide derivative (I) or a salt thereof is usually about 0.1 to 80% by weight, preferably about 1 to 20% by weight, based on the whole preparation.
  • sulfonide derivative (I) or a salt thereof when used in emulsions, solutions, wettable powders (eg, water-dispersible granules), aqueous suspension preparations, microemulsions, etc., they are usually about 1 to 80% by weight, preferably about 1 to 80% by weight. About 20% by weight is appropriate.
  • the amount is usually about 0.1 to 50% by weight, preferably about 1 to 20% by weight.
  • the amount is usually about 5 to 50% by weight, preferably about 1 to 20% by weight.
  • Other pesticidal active ingredients eg, insecticides, acaricides, herbicides and Z or microbicides
  • incorporated in the composition of the present invention are usually about 1 to 80% by weight based on the total amount of the preparation. The preferred is about 1 to 20 weight. /. Used in a range of degrees.
  • the content of additives other than the above-mentioned active ingredients varies depending on the type or content of the pesticidal active ingredient or the dosage form of the preparation, but is usually about 0.001 to 99.9% by weight, preferably about 1%.
  • the surfactant is usually about 1 to 20% by weight, preferably about 1 to 15% by weight, and the flow aid is about 1 to 20% by weight based on the total amount of the composition. It is preferable to add about 1 to 90% by weight, preferably about 1 to 70% by weight, of the carrier. Specifically, when a liquid preparation is produced, a surfactant is usually added in an amount of about 1 to 20% by weight, preferably about 1 to 10% by weight, and water is added in an amount of about 20 to 90% by weight. Is preferred.
  • the emulsion, water-dispersible powder (eg, water-dispersible granule) and the like are preferably diluted with water or the like and increased in volume (for example, about 100 to 5,000 times) before spraying.
  • the sulfonide derivative (I) or a salt thereof can be prepared, for example, by condensing a specific raw material compound shown in the following method A and method B, or by converting a specific raw material compound shown in the method C into two or more. Can be manufactured.
  • the leaving group L is, for example, a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, for example, a benzenesulfo-loxy group, a p-toluenesulfo -Represents an aromatic sulfonyloxy group such as a 4-hydroxyl-benzenebenzenesulfonyloxy group.
  • halogen atom such as iodine atom
  • main butoxy group an ethoxy group
  • ⁇ preparative 3 alkoxy group such as a propoxy group, for example methylthio group, Echiruchio group
  • ⁇ preparative 3 alkylthio group such as a propylthio group, e.g. methane sulfide El group, Etansurufuie group, such as propane sulfide El group.
  • C 3 s- alkane sulfonyl groups such as methans / lefonyl groups, ethanes-no-lefonyl groups, propanesulfonyl groups, etc.
  • Aromatic sulfonyl groups such as benzene sulfoninole group and 4-nitrobenzene sulfoninole group; alkane sulfooxy groups such as methanesulfonyloxy, ethanesulfuroxy and propanesulfonyloxy groups; and benzenesulfonylo
  • Aromatic sulfooxy groups such as xy group, p-toluenesulfonyloxy group, 4-nitrobenzenesulfonyloxy group, phenoxy group and the like.
  • Solvents used in a solvent include, for example, petroleum ether, pentane, hexane, and cyclohexane, hydrocarbons such as hexane, benzene, toluene, and xylene, for example, dichloromethane, chlorohonolem, and tetrahydrocarbon.
  • Halogenated hydrocarbons such as 1,2-dichloroethane, 1,2-dichloroethylene, trichloroethylene, and benzene, for example, dimethyl ether, diisopropylether, tetrahydrofuran, 1,4-dioxane, dimethoxetane, ethylene glycolone Aethenoles such as monomethinole ether and diethylene glycol dimethyl ether; esters such as ethyl acetate and butyl acetate; ketones such as acetone and methyl ethyl ketone; and nitrinoles such as acetonitrile and propionitrile
  • amides such as N, N-dimethylformamide, N, N-dimethylacetamide, and N-methinolepyrrolidone
  • sulfoxides such as dimethyl sulfoxide
  • sulfones such as sulfolane
  • Examples of such compounds include
  • Acids or bases may be added to promote the reaction, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, sulfuric acid, nitric acid, perchloric acid
  • Inorganic acids such as acids, for example, formic acid, acetic acid, propionic acid, trifluoroacetic acid, tartaric acid, malic acid, citric acid, oxalic acid, succinic acid, benzoic acid, picric acid, methanesulfonic acid, -toluenesulfonic acid, trifluorosulfonic acid
  • the base include organic acids such as methanesulfonic acid and the like.
  • the base examples include metal hydroxides such as lithium hydroxide, sodium hydroxide, hydroxy potassium and hydroxy calcium hydroxide, for example, sodium carbonate, potassium carbonate, and the like.
  • Metal carbonates such as sodium bicarbonate and hydrogen bicarbonate, metal water such as sodium hydride, hydrogen hydride and calcium hydride
  • Metal amides such as lithium disopropylamide, sodium amide and potassium amide
  • organic lithium reagents such as methyllithium, n_butyllithium, sec-butyllithium, tert-butyllithium and phenyllithium ,
  • organic magnesium reagents such as methylmagnesium bromide and ethylmagnesium chloride
  • metals such as lithium metal, sodium metal, metal spheres, and the like, for example, trimethylamine, triethylamine, disodium Propylethylamine, N, N-dimethylaniline, pyridine, lutidine,
  • Organic salts such as And the like.
  • the raw material represented by the formula (VI) can be produced by a method similar to the method A or the method B or a method analogous thereto.
  • Method C is 30 to 30%; LOO% nitric acid and fuming nitric acid are commonly used, for example, alkali metal nitrates such as sodium nitrate and potassium nitrate, and alkyl nitrates such as ethyl nitrate and amyl nitrate. , nitro Yu arm tetrafluoropropoxy O b Poreto (N 0 2 BF 4), nitro E ⁇ beam triflate Ruo b methanesulfonate (N 0 2 CF 3 S 0 3), nitrogen oxides (e.g., N_ ⁇ 2, N 2 0 3 it may be used N 2 0 There N 2 0 5) or the like.
  • alkali metal nitrates such as sodium nitrate and potassium nitrate
  • alkyl nitrates such as ethyl nitrate and amyl nitrate.
  • nitrogen oxides e.g., N_ ⁇ 2, N 2
  • the nitrating agent can be used in an amount of about 1.0 to 20 equivalents based on the raw material (VI), but is preferably 1.0 to 10 equivalents when nitric acid is used. Further, when using 90% or more of nitric acid, about 1.0 to 3.0 equivalent is preferable.
  • the nitration reaction may be carried out without solvent, but is usually carried out in the presence of an acidic solvent such as sulfuric acid, acetic acid, acetic anhydride, anhydrous trifluoroacetic acid, and trifluorosulfonic acid. If desired, a solvent which does not adversely influence the reaction or a mixture thereof may be used.
  • Such a solvent examples include the same solvents as those described in Method A or Method B, in addition to the acidic solvents described above. These solvents can be used alone, or, if necessary, two or more (preferably two to three) in an appropriate ratio, for example, about 1: 1 to 1:10 (by volume) ) May be used as a mixture.
  • reaction solvent is not homogeneous, for example, triethylbenzylammonium chloride, tri-n-octylmethylammonium chloride, trimethyldecylammonium chloride, tetramethylammonium-bromobromide, cetyl
  • the reaction may be carried out in the presence of a quaternary ammonium salt such as pyridinium bromide or a phase transfer catalyst such as crown ethers.
  • Particularly preferred solvents are acetic acid and acetic anhydride.
  • the temperature of this reaction is usually in the range of about 150 to 200 ° C, preferably about 120 to: L30 ° C. Reaction times range from about 1 minute to 48 hours, preferably from about 15 minutes to 10 hours.
  • the figures in parentheses indicate the volume mixing ratio of each solvent.
  • the NMR (nuclear magnetic resonance) spectrum indicates proton NMR, which was measured with a Bruker AC-200P (200 MHz) spectrometer using tetramethylsilane as the internal standard. Values are given in ppm.
  • the abbreviations used in the following Reference Examples, Examples and Tables have the following meanings.
  • the sulfonanilide derivative (I) shown in Table 2 was produced by the same method as in the above example or a method analogous thereto.
  • the symbol A in the production method column indicates that it was produced by the same method as in Example 1 or Example 2 or a method analogous thereto, and the symbol B indicates that it was produced by the same method as Example 3 or a method analogous thereto.
  • the symbol C indicate that the compound was produced by the same method as in Example 4 or Example 5, or a method analogous thereto, but the method for producing each compound is limited to the method described in Table 2. It should not be. +
  • the prepared drug solution was irrigated into soil contaminated with clubroot so that the active ingredient was 353.7 mg / m 2 , mixed well, and then seeded with Komatsuna. After cultivation in a greenhouse for 4 to 6 weeks, the roots of Komatsuna were washed out and examined for disease severity, and the results were expressed using the following control values.
  • Control value 3 Disease severity 30% or less
  • Control value 2 Disease severity 31-40%
  • Control value 1 Disease severity 41 to 50%
  • Control value 0 Disease incidence 5 1% or more Table 3 ⁇ Control test results
  • the sulfonanilide derivative (I) or a salt thereof has a microbicidal action, has a small effect on human animals, natural enemies, the environment, fish, and crops, is safe, and has an excellent control effect on drug-resistant microorganisms. Therefore, it is useful as an excellent agricultural and horticultural microbicide. In particular, it has an excellent control effect on soil diseases such as root-knot disease of cruciferous plants (for example, canola, potato, cauliflower, cabbage, komatsuna, rapeseed, Chinese cabbage) and diseases caused by Aphanomyces genus bacteria. Have.

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Abstract

L'invention concerne des compositions microbicides utilisées dans le domaine agricole et horticole, et contenant comme ingrédient actif des dérivés de sulfonanilide représentés par la formule générale (I) ou leurs sels. Lesdites compositions peuvent être utilisées en toute sécurité de par leur faible influence sur les êtres humains, les animaux domestiques, les ennemis naturels, l'environnement, les poissons et les récoltes, et elles ont d'excellents effets même sur les microbes résistants.
PCT/JP2001/009178 2000-10-23 2001-10-19 Compositions microbicides utilisees dans le domaine agricole et horticole et contenant des derives de sulfonanilide WO2002034049A1 (fr)

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JP2009520738A (ja) * 2005-12-22 2009-05-28 ノバルティス アクチエンゲゼルシャフト Ｃｃｒ９活性の阻害剤
CN106008288A (zh) * 2016-06-15 2016-10-12 西北农林科技大学 一种苯磺酰胺类化合物及其用途
CN113322285A (zh) * 2021-06-02 2021-08-31 青岛农垦海洋生物股份有限公司 一种利用荧光假单胞菌发酵生产诺尔霉素的方法
CN114163362A (zh) * 2021-12-31 2022-03-11 山东第一医科大学(山东省医学科学院) 一种n-苯磺酰基-4-卤-2-硝基苯胺制备方法

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Cited By (5)

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Publication number Priority date Publication date Assignee Title
JP2009520738A (ja) * 2005-12-22 2009-05-28 ノバルティス アクチエンゲゼルシャフト Ｃｃｒ９活性の阻害剤
CN106008288A (zh) * 2016-06-15 2016-10-12 西北农林科技大学 一种苯磺酰胺类化合物及其用途
CN113322285A (zh) * 2021-06-02 2021-08-31 青岛农垦海洋生物股份有限公司 一种利用荧光假单胞菌发酵生产诺尔霉素的方法
CN114163362A (zh) * 2021-12-31 2022-03-11 山东第一医科大学(山东省医学科学院) 一种n-苯磺酰基-4-卤-2-硝基苯胺制备方法
CN114163362B (zh) * 2021-12-31 2023-04-07 山东第一医科大学(山东省医学科学院) 一种n-苯磺酰基-4-卤-2-硝基苯胺制备方法

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