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WO2005122761A1 - Composition bactéricide - Google Patents

Composition bactéricide Download PDF

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Publication number
WO2005122761A1
WO2005122761A1 PCT/JP2005/011214 JP2005011214W WO2005122761A1 WO 2005122761 A1 WO2005122761 A1 WO 2005122761A1 JP 2005011214 W JP2005011214 W JP 2005011214W WO 2005122761 A1 WO2005122761 A1 WO 2005122761A1
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Prior art keywords
group
formula
alkyl group
atom
compound represented
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PCT/JP2005/011214
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English (en)
Japanese (ja)
Inventor
Masato Soma
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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Publication of WO2005122761A1 publication Critical patent/WO2005122761A1/fr
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A01N47/14—Di-thio analogues thereof

Definitions

  • X represents an oxygen atom or a sulfur atom
  • the present invention provides a method for controlling a plant disease, which comprises applying an effective amount of the compound (I) and the compound (II) to a plant or soil where the plant grows.
  • a method for controlling a plant disease which comprises applying an effective amount of the compound (I) and the compound (II) to a plant or soil where the plant grows.
  • Examples of the halogen atom represented by R 1 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and examples of the C 11 -C 4 alkyl group include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
  • C1-C2 alkyl groups include methyl and ethyl groups;
  • C1-C4 haloalkyl groups include, for example, Examples include a fluoromethyl group, a difluoromethyl group and a trifluoromethyl group.
  • Examples of the 02-4-alkenyl group include a vinyl group, a 1-methylvinyl group, a 1-propenyl group, a 2-propenyl group, and a 1-methyl- A 2-propenyl group, a 2-methyl-2-propyl group, a 2-butenyl group and a 3-butenyl group.
  • Examples of the C 2 -C 4 alkynyl group include an ethynyl group, A C1-C4 alkoxy group such as a methoxy group, an ethoxy group, a propoxy group, and an isopropoxy group.
  • Examples of the C1-C4 alkoxy group include a methoxy group, a ethoxy group, a propoxy group, and an isopropoxy group. Butoxy group, isobutoxy group, sec-butoxy group and tert-butoxy group.
  • Examples of the C1-C4 haloalkoxy group include fluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, Examples include a 2,2-trifluoroethoxy group, a 1,1,2,2-tetrafluoroethoxy group and a 2-fluoroethoxy group.
  • Examples of the C 2 -C 4 alkynyl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-methyl-2-propynyl group, a 2-butynyl group and a 3-butynyl group.
  • the C 3- C 5 polymethylene group and R 1 and R 2 has decreased together, trimethylene group, and tetramethylene group and a pentamethylene group, the C 3- C 4 Porimechire down, trimethylene and tetramethylene And methylene groups.
  • Examples of the C 1 -C 4 alkyl group represented by R 5 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group and a tert-butyl group.
  • Examples of the 2 alkyl group include a methyl group and an ethyl group
  • examples of the C 3 -C 4 alkenyl group include a 2-propenyl group, a 1-methyl-2-propenyl group, and a 2-methyl-2-propyl group.
  • X is an oxygen atom or a sulfur atom
  • R 1 is a halogen atom or a C 1 -C 2 alkyl group
  • R 2 is a hydrogen atom
  • X is an oxygen atom
  • R 1 is hydrogen Atom, halogen atom or C1-C2 alkyl group
  • R 2 is a hydrogen atom or a halogen atom
  • R 1 and R 2 are taken together to form a C 3 -C 4 polymethylene group or 1,3-butadiene 1
  • R 4 is a C 1 -C 2 alkyl group
  • R 5 is a CI—C 2 alkyl group, a C 3 alkenyl group or a C 3 alkynyl group.
  • Table 1 shows specific examples of the compound (I) together with the compound number.
  • a compound represented by the formula (2-1) wherein X is an oxygen atom and a compound represented by the formula (2-2) wherein X is a sulfur atom are produced, for example, according to the following scheme. can do.
  • R 2 represents a hydrogen atom, a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 2 -C 4 alkenyl group or a C 2 -C 4 alkynyl group, or R 1 and R 2 represent Together represent a C3-C5 polymethylene group or a 1,3-butadiene-1,4-diyl group,
  • R 4 represents a C 1 -C 3 alkyl group
  • R 6 represents a methyl group, an ethyl group or a propyl group
  • L 1 represents a chlorine atom or a bromine atom
  • L 2 represents a halogen atom
  • the reaction is carried out in the presence or absence of a solvent, usually in the presence of a base.
  • a solvent usually in the presence of a base.
  • the solvent used in the reaction include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, tert-butyl methyl ether, and aliphatic hydrocarbons such as hexane, heptane, and octane; Aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as benzene and the like, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile and butylonitrile, N, N-dimethylformamide And sulfoxides such as dimethyl sulfoxide and mixtures thereof.
  • ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glyco
  • the amount of the reagent used in the reaction is usually 1 to 10 mol of the base and 1 to 5 mol of the compound of the formula (4) per 1 mol of the compound of the formula (3). is there.
  • the reaction temperature of the reaction is usually in the range of 0 to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound represented by the formula (5) is isolated by pouring the reaction mixture into water, extracting with an organic solvent, and performing a post-treatment operation such as drying and concentration of the organic layer. Can be.
  • the isolated compound represented by the formula (5) can be further purified by operations such as chromatography and recrystallization. Process ((1)-2)
  • the compound represented by the formula (7) can be produced by reacting the compound represented by the formula (5) with the compound represented by the formula (6).
  • the reaction is performed in the presence of a base in the presence of a solvent.
  • Examples of the base used in the reaction include carbonates such as sodium carbonate and potassium carbonate, alkali metal hydrides such as sodium hydride and potassium hydride, sodium methoxide, sodium ethoxide and potassium tert-butoxide. Metal alkoxides.
  • the amount of the reagent used in the reaction is usually a ratio of 1 to 10 mol of the base to 1 mol of the compound of the formula (5), and a ratio of 1 to 5 mol of the compound of the formula (6). It is.
  • the compound represented by the formula (7) is isolated by pouring the reaction mixture into water, extracting the organic solvent, and performing a post-treatment operation such as drying and concentration of the organic layer. Can be.
  • the isolated compound represented by the formula (7) can be further purified by operations such as chromatography and recrystallization.
  • Process ((1) 1 3) The compound represented by the formula (8) can be produced by reacting the compound represented by the formula (7) with hydrogen in the presence of a hydrogenation catalyst.
  • the reaction is usually performed in a hydrogen atmosphere, usually in the presence of a solvent.
  • the amount of the hydrogenation catalyst used in the reaction is usually 0.001 to 0.5 mol per 1 mol of the compound represented by the formula (7).
  • the reaction is usually performed under a hydrogen atmosphere at 1 to 100 atm.
  • the reaction can be carried out in the presence of an acid (such as hydrochloric acid) if necessary.
  • an acid such as hydrochloric acid
  • the reaction temperature of the reaction is usually in the range of 120 to 100 ° C., and the reaction time is usually 0.20.
  • the range is 1-2 hours.
  • the compound represented by the formula (10) can be produced by reacting a compound represented by the formula (8) with a compound represented by the formula (9).
  • reaction is carried out in the presence or absence of a solvent, usually in the presence of a base.
  • aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as ethyl benzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile and ptyronitrile, N, N-dimethylformamide and the like
  • aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as ethyl benzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile and ptyronitrile, N, N-dimethylformamide and the like
  • acids amides such as dimethyl sulfoxide, and mixtures thereof.
  • Examples of the base used in the reaction include carbonates such as sodium carbonate and potassium carbonate, triethylamine, diisopropylethylamine, 1,8-diaza Tertiary amines such as bicyclo [5.4.0] pendec 7-ene, 1,5-diazabicyclo [4.3.0] non-5-ene and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine Group compounds.
  • the reaction temperature of the reaction is usually in the range of 0 to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound represented by the formula (10) can be isolated by performing post-treatment operations such as adding an organic solvent to the reaction mixture, if necessary, followed by filtration and concentration of the filtrate. .
  • the isolated compound represented by the formula (10) can be further purified by an operation such as distillation, chromatography, and recrystallization.
  • the compound represented by the formula (11) can be produced by reacting the compound represented by the formula (10) with water in the presence of a base.
  • the reaction is usually performed in the presence of water and an organic solvent.
  • organic solvent used in the reaction examples include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether; aromatic hydrocarbons such as toluene and xylene; Examples include halogenated hydrocarbons such as benzene, nitriles such as acetonitrile and ptyronitrile, alcohols such as methanol, ethanol, and propanol, and mixtures thereof.
  • ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether
  • aromatic hydrocarbons such as toluene and xylene
  • halogenated hydrocarbons such as benzene, nitriles such as acetonitrile and ptyronitrile, alcohols such as methanol, ethanol, and propanol, and mixtures
  • Examples of the base used in the reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide.
  • the amount of the base used in the reaction is usually 1 to 10 mol per 1 mol of the compound represented by the formula (10).
  • the reaction temperature of the reaction is usually in the range of 0 to 150, and the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound represented by the formula (12) can be produced by reacting the compound represented by the formula (11) with a chlorinating agent.
  • chlorinating agent used in the reaction examples include thionyl chloride, oxalyl chloride and phosphorus oxychloride.
  • the reaction temperature of the reaction is usually in the range of 30 to 150 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound represented by the formula (12) can be isolated by performing an operation such as concentration of the reaction mixture as it is.
  • the isolated compound represented by the formula (12) is used as it is in the reaction of the next step.
  • the compound represented by the formula (2-1) can be produced by reacting the compound represented by the formula (12) with the compound represented by the formula (13).
  • the reaction is usually performed in the presence of a solvent and in the presence of a base.
  • solvent used in the reaction examples include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether; and aliphatic hydrocarbons such as hexane, heptane, and octane.
  • Aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as benzene benzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile and butylonitrile, N, N— Acid amides such as dimethylformamide, dimethyls Sulfoxides such as rufoxide and mixtures thereof.
  • Examples of the base used in the reaction include carbonates such as sodium carbonate and potassium carbonate, triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] pendec-7-ene, 1,5 —Diazabicyclo [4.3.0] non— Tertiary amines such as 5-ene and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
  • the amount of the reagent used in the reaction is usually 1 to 10 mol of the base to 1 mol of the compound represented by the formula (12), and 1 to 5 mol of the compound represented by the formula (13) usually. It is.
  • the reaction temperature of the reaction is usually in the range of 20 to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
  • the reaction mixture After the completion of the reaction, (i) the reaction mixture is poured into water and extracted with an organic solvent. After washing, drying and concentration, or (ii) a post-treatment operation such as adding a small amount of water to the reaction mixture, concentrating under reduced pressure, and collecting the obtained solid by filtration, yields the formula (2) —
  • the compound of 1) can be isolated.
  • the isolated compound represented by the formula (2-1) can be further purified by a technique such as chromatography and recrystallization. Process ((1) i 8)
  • the reaction is usually performed in the presence of a solvent.
  • Examples of the solvent used in the reaction include acid amides such as N, N-dimethylformamide, sulfoxides such as dimethylsulfoxide, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixtures thereof.
  • the amount of the reagent used in the reaction is such that the compound represented by the formula (13) is usually in a ratio of 1 to 3 mol per 1 mol of the compound represented by the formula (11), and the dehydrating agent is usually used.
  • the ratio is 1 to 5 mol.
  • the reaction temperature of the reaction is usually in the range of 0 to 140 ° C., and the reaction time is usually 0.:! ⁇ 24 hours range.
  • solvent used in the reaction examples include 1,4-dioxane, tetrahydrofuran, ethers such as ethylene glycol dimethyl ether and tert-butyl methyl ether, aliphatic hydrocarbons such as hexane, heptane, and octane; Aromatic hydrocarbons such as benzene and xylene; halogenated hydrocarbons such as chlorobenzene; nitriles such as acetonitrile and ptyronitrile; sulfoxides such as dimethylsulfoxide; and mixtures thereof.
  • the amount of the Lawson reagent used in the reaction is usually 1 to 10 mol per 1 mol of the compound represented by the formula (2-1).
  • the reaction temperature of the reaction is usually in the range of 50 to 150 ° C, and the reaction time is usually in the range of 0.5 to 24 hours.
  • Examples of the dehydrating agent used in the reaction include WSC, carbodiimides such as 1,3-dicyclohexyl carbodiimide.
  • the reaction temperature of the reaction is usually in the range of 0 to 140 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound represented by the formula (2-3) can also be produced by reacting the compound represented by the formula (15) with the compound represented by the formula (12) in the presence of a base.
  • the reaction is usually performed in the presence of a solvent.
  • solvent used in the reaction examples include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, tert-butyl methyl ether, and aliphatic hydrocarbons such as hexane, heptane, and octane.
  • Examples of the base used in the reaction include carbonates such as sodium carbonate and potassium carbonate, triethylamine, diisopropylethylamine, 1,8-diaza Tertiary amines such as bicyclo [5.4.0] pentadec-7-ene, 1,5-diazabicyclo [4.3.0] non-5-ene and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine Group compounds.
  • the amount of the reagent used in the reaction is usually 1 to 10 mol of the base per 1 mol of the compound represented by the formula (12), and 1 to 5 mol of the compound represented by the formula (15) usually. It is.
  • the reaction mixture is poured into water and extracted with an organic solvent, and the organic layer is optionally treated with acidic water (dilute hydrochloric acid, etc.) and / or basic water (sodium hydrogen carbonate aqueous solution, etc.) After washing, drying and concentration, or (ii) a post-treatment operation such as adding a small amount of water to the reaction mixture, concentrating under reduced pressure, and collecting the obtained solid by filtration, yields the formula (2) —
  • the compound of 3) can be isolated.
  • the isolated compound represented by the formula (2-3) can be further purified by a technique such as chromatography and recrystallization.
  • the compound represented by the formula (13) can be produced, for example, by reacting a compound represented by the formula (16) with a cyanide, an ammonium salt and an ammonium salt.
  • the reaction is usually performed in the presence of a solvent.
  • ammonium salt used in the reaction examples include ammonium chloride and ammonium bromide.
  • the amount of the reagent used in the reaction is usually 1 to 5 mol of the cyanide, 1 to 5 mol of the ammonium salt usually, and ammonia is usually 1 mol of the compound of the formula (16). The ratio is from 1 mol to a large excess.
  • the reaction temperature of the reaction is usually in the range of 110 to 100 ° C, and the reaction time is usually in the range of 1 to 50 hours.
  • 34.5 mg of N- (3,4-dimethylpentyl) -13- ⁇ 3-methoxy-14- (2-propieroxy) phenyl ⁇ propanethioamide) was obtained.
  • a mixed solution of 0.50 g of [phenyl] propion chloride and 3 ml of tetrahydrofuran was added at 0 to 5 ° C, and the mixture was stirred at room temperature for 1 hour. Thereafter, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with 5% hydrochloric acid, water, a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, dried over magnesium sulfate, and concentrated under reduced pressure.
  • a mixture of 31 g of aluminum chloride and 15 Oral of methylene chloride was ice-cooled, 30 g of ethyl oxalyl chloride was mixed, and the mixture was stirred under ice-cooling for 30 minutes.
  • the obtained mixture was gradually added to a mixture of 22 g of indane and 200 ml of methylene chloride under ice-cooling, followed by stirring at room temperature for 1 hour.
  • N- (5,6,7,8-tetrahydronaphthalene-l-2-ylmethyl) -13- ⁇ 3-methoxy-41- (2-propynyloxy) phenyl ⁇ propanamide 637mg, mouth reagent 769mg and tetrahydrofuran 1 Om1 was mixed and stirred at 65 ° C. for 3 hours. Thereafter, the reaction mixture was cooled and concentrated under reduced pressure. Water was added to the residue and extracted with ethyl acetate. The organic layer was sequentially washed with 5% hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure.
  • the ethylenebisdithiocarbamate compound means a salt of ethylenebisdithiocarbamate.
  • the ethylenebisdithiocarbamate compounds include zineb (generic name) [chemical name: zinc ethylenebis (di thiocarbamete) (polymeric)], maneb (generic name) [chemical name: manganese ethylenebis (dithiocarb teba polymeric)] and mansef (Generic name) [manganese ethylenebis (di thiocarbamete; (polymeric) complex with zinc salt]).
  • composition of the present invention include, for example, the following.
  • X is an oxygen atom or a sulfur atom
  • R 1 is a halogen atom or a C 1 -C 2 alkyl group
  • R 2 is a hydrogen atom, a halogen atom or a C A force that is a 1-C 2 alkyl group, or R 1 and R 2 together form a C 3 -C 4 polyethylene group or a 1,3-butadiene 1,4-diyl group
  • R 3 is hydrogen
  • X is an oxygen atom
  • R 1 is a hydrogen atom, a halogen atom or a C 1 -C 2 alkyl group
  • R 2 is a hydrogen atom or a halogen atom
  • R 1 and R 2 are joined together to form a C3-C4 polymethylene group or 1,3-butadiene-1,4-diyl group
  • R 3 is a cyano group
  • R 4 is a C 1 -C 2 alkyl group.
  • the amide compound represented by the formula (1) is N— (4-cyclobenzyl) 13- ⁇ 3-methoxy-41- (2-propynyloxy) phenyl ⁇ propanamide (i) Or the bactericidal composition of (ii).
  • the composition of the present invention includes, for example, rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), crest blight;) hei (Rhizoctonia solani)> barley powdery mildew (Erysiphe graminis, f. Sp. , f. sp.triticu, Fusarium head blight (Gibberella zeae), Rust (Puccinia str i if ormis, P. graminis, P.
  • the mixing ratio of the compound (I) and the compound (II) is not particularly limited. 0 parts by weight, preferably in the range of 0.5 to 50 parts by weight. That is, in the composition of the present invention, the mixing ratio of the compound (I) and the compound (II) is usually from 10: 1 to 1: 100, preferably from 2: 1 to L: 50.
  • composition of the present invention may be a mixture of the compound (I) and the compound (II) itself, but is usually a solid carrier, a liquid carrier, or a gaseous carrier, if necessary, a surfactant, a fixing agent, a dispersant, Formulation into wettable powders, suspensions, granules, dry floor tablets, emulsions, aqueous liquids, oils, smokers, aerosols, microcapsules, etc. .
  • composition of the present invention can be prepared by mixing the formulated compound (I) with the formulated compound (II).
  • Compound (I) and compound (II) can be mixed at the time of application.
  • These preparations usually contain the active ingredient compound in a total amount of 0.1 to 99% by weight, preferably 0.2 to 90% by weight.
  • Solid carriers include clays (kaolin clay, diatomaceous earth, synthetic hydrous silicon oxide, attapulgite clay, bentonite, acid clay, etc.), talcs, and other inorganic minerals (sericite, quartz powder, sulfur powder) , Activated carbon, calcium carbonate, hydrated silica, etc.) and fine powders or granules such as chemical fertilizers (ammonium sulfate, phosphorous ammonium, ammonium nitrate, urea, salt ammonium, etc.).
  • the liquid carrier include water, alcohols and the like.
  • gaseous carrier examples include butane gas, carbon dioxide gas, and fluorocarbon gas.
  • Surfactants include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and their polyoxyethylenates, polyethers. Tylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives and the like.
  • fixatives and dispersants include casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, saccharides, synthetic water-soluble polymers (polyvinyl alcohol, polypinyl pyrrolyl).
  • composition of the present invention is applied as it is or diluted with water to a plant or a soil where the plant grows.
  • the formulation or its water dilution is sprayed on the soil surface, and the formulation or its water dilution is mixed with the soil.
  • the application rate is determined by the type of the active ingredient compound, the mixing ratio, the weather conditions, the formulation, the application time, the application method, the application place, and the control. It can be varied depending on the type of the target disease, the type of the crop to be controlled, etc., but is usually 0.01 to from the total amount of the active ingredient compound per 10 Om 2 : L 000 g, preferably 0.1 to : LOO g.
  • Emulsions, wettable powders, suspensions, and the like are usually diluted with water so that the active ingredient concentration is 0.0001 to 1% by weight, preferably 0.001 to 0.5% by weight. And powders are usually applied as they are.
  • the preparation of the composition of the present invention can also be used in treatment methods such as seed treatment and ULV.
  • the seed treatment method include a seed dressing treatment with the composition of the present invention, a seed immersion treatment in the composition of the present invention, and a seed spraying treatment of the composition of the present invention.
  • the application rate is usually from 0.01 to 50 g, preferably from 0.01 to: LO g, based on the total amount of the active ingredient compound per kg of seed.
  • the composition of the present invention can be used together with other fungicides, insecticides, acaricides, nematicides, herbicides, fertilizers, soil conditioners, and the like.
  • the present invention will be described in more detail with reference to formulation examples and test examples, but the present invention is not limited to the following examples. Parts represent parts by weight.
  • E Expected control value (%) when active compound A is treated with mppm and active compound B is treated with nppm (hereinafter referred to as expected control value)
  • a plastic pot was filled with sandy loam and sown with grapes (variety: Berry A). The plant was grown in a greenhouse for 40 days.
  • a test agent prepared as a wettable powder according to Formulation Example 5 was diluted to a predetermined concentration with water, and sprayed with foliage so as to adhere sufficiently to the leaf surface of a grape seedling having three true leaves developed.
  • a suspension of zoosporangia of the grape downy mildew was spray-inoculated to the foliage of the seedling of the grape. After inoculation, the grape seedlings were allowed to stand overnight at 23 T and high humidity, and then grown in a greenhouse for 7 days.
  • composition of the present invention has an excellent effect in controlling plant diseases, and particularly exhibits an excellent effect in controlling plant diseases caused by alga (egg fungi) such as downy mildew and plague.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention décrit une composition bactéricide contenant un composé d’amide représenté par la formule (1) figurant ci-dessous et un composé d’éthylènebisdithiocarbamate en tant qu’ingrédients actifs. La présente invention décrit également une méthode pour contrôler les maladies végétales dans laquelle le composé d’amide représenté par la formule (1) figurant ci-dessous et le composé d’éthylènebisdithiocarbamate sont appliqués à une plante ou au sol sur lequel pousse la plante. (1)
PCT/JP2005/011214 2004-06-17 2005-06-14 Composition bactéricide Ceased WO2005122761A1 (fr)

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JP2004179470 2004-06-17
JP2004-179470 2004-06-17

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WO2005122761A1 true WO2005122761A1 (fr) 2005-12-29

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103039597A (zh) * 2012-12-27 2013-04-17 中国检验检疫科学研究院 一种针对水果采后真菌病害的丙酸热水处理技术及应用

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58140055A (ja) * 1982-02-12 1983-08-19 Sumitomo Chem Co Ltd Ｎ−ベンジル−フエニルアセトアミド誘導体、その製造法およびこれらを有効成分として含有する農園芸用殺菌剤
WO2004058685A1 (fr) * 2002-12-24 2004-07-15 Sumitomo Chemical Company, Limited Amide et procede de lutte contre les maladies des plantes au moyen de ce compose

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