WO1998002414A1 - Composes de n-phenylcarbamate, procede de preparation de ces composes et bactericides agricoles et horticoles - Google Patents

Composes de n-phenylcarbamate, procede de preparation de ces composes et bactericides agricoles et horticoles Download PDF

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Publication number
WO1998002414A1
WO1998002414A1 PCT/JP1997/002417 JP9702417W WO9802414A1 WO 1998002414 A1 WO1998002414 A1 WO 1998002414A1 JP 9702417 W JP9702417 W JP 9702417W WO 9802414 A1 WO9802414 A1 WO 9802414A1
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Prior art keywords
carbon atoms
group
compound
alkyl group
formula
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PCT/JP1997/002417
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English (en)
Japanese (ja)
Inventor
Masanori Watanabe
Toshinobu Tanaka
Shin Suizu
Takehiko Asahara
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Ube Industries, Ltd.
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Publication of WO1998002414A1 publication Critical patent/WO1998002414A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/58—Derivatives of thiocarboxylic acids, the doubly-bound oxygen atoms being replaced by nitrogen atoms, e.g. imino-thio ethers
    • 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
    • A01N47/20—N-Aryl derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Definitions

  • N-phenyl carbamate compound its production method and fungicide for agricultural and horticultural use
  • the present invention relates to a novel N-phenylcarbamate compound useful as a fungicide for pus horticulture.
  • N-phenyl carbamate compounds have bactericidal activity (for example, W093- 3504, JP-A-5-170726, Japanese Unexamined Patent Application Publication No. Hei 6-5-67556, Japanese Unexamined Patent Publication No. Hei 6-271715, Japanese Unexamined Patent Publication No. Hei 6-34007, and Japanese Unexamined Patent Publication No. Hei 7-145137. ).
  • N-phenyl carbamate compounds cannot be said to have sufficient bactericidal activity.
  • compounds having more excellent bactericidal activity are required.
  • the present invention is as follows.
  • the first invention has the following formula (1):
  • R 1 is a hydrogen atom, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, an alkynyl group having 3 to 5 carbon atoms, an alkoxyalkyl group having 2 to 5 carbon atoms, number 3-5 alkenyl group or C - C0 2
  • R 4 represents; in here, R 4 represents a Sumifukuro number 1-4 alkyl groups;
  • R 2 is 1-4 alkyl group having a carbon number
  • R 3 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cyano group, an alkoxy group having 1 to 4 carbon atoms, and a carbon atom having 1 to 4 carbon atoms.
  • R 2 has the same meaning as described above;
  • X is a chlorine atom or a bromine atom; a compound represented by the following formula (compound (2)):
  • R 2, 8 3, and (1 is the same as defined above,
  • the present invention relates to a method for producing an N-phenyl carbamate compound (compound (1-a)) represented by
  • a third invention relates to the above compound (1-1a)
  • R 1 ′ is an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, an alkynyl group having 3 to 5 carbon atoms, an alkoxyalkyl group having 2 to 5 carbon atoms or one C 0 2 represents R 4 ; wherein represents an alkyl group having 1 to 4 carbon atoms; and Y represents a chlorine atom, a bromine atom,
  • R 1 ′, R 2 , 3 and 1 ⁇ are as defined above,
  • the present invention relates to a method for producing an N-phenyl carbamate compound (compound (1-b)) represented by
  • the fourth invention is a first invention.
  • R 1 represents an alkoxy group having 1 to 4 carbon atoms
  • R 2 and X are as defined above,
  • R ′, R 2 , R 3 and n are as defined above,
  • the present invention relates to a method for producing an N-phenyl carbamate compound (compound (1-c)) represented by
  • the fifth invention relates to a fungicide for agricultural and horticultural use containing the compound (1) as an active ingredient.
  • R ′ to R 4 represented by the novel N-phenyl carbamate compound as the target compound and the raw material for producing the compound are as follows.
  • R ′ is a hydrogen atom, an alkoxy group having 4 to 4 carbon atoms, an alkyl group having 4 to 4 carbon atoms, an alkynyl group having 3 to 5 carbon atoms, an alkoxyalkyl group having 2 to 5 carbon atoms can 3-5 alkenyl group or a carbon C0 2 R 4 is exemplified, this Here, R 4 represents an alkyl group having 4 to 4 carbon atoms. Examples of the alkyl group include a linear or branched one, and preferably CH 3 .
  • the alkoxy group there may be mentioned a straight or branched, good Mashiku is CH 3 0, C 2 H 5 0.
  • alkyl group examples include a linear or branched one, and preferably C 2 H S.
  • alkynyl group examples include straight-chain or branched ones, and preferably HC ⁇ CCH 2 .
  • alkoxyalkyl group although Ru may be mentioned a straight or branched, preferably Flip 1 "1 3 0_Rei_1 ⁇ 1 2 Dearu.
  • alkenyl group examples include a linear or branched alkenyl group, and preferably CH 2 CHCHCH 2 .
  • R ′ examples include the same alkyl group, alkenyl group, alkynyl group, alkoxyalkyl group and —CO 2 R 4 (R 4 has the same meaning as described above) as described for R 1 .
  • the R " include the same alkoxy groups as mentioned in R 1.
  • R 2 examples include an alkyl group having 1 to 4 carbon atoms.
  • the alkizole group may be a straight-chain or branched one, and is preferably CH 3 or C 2 H 5 .
  • R 3 includes a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cyano group, an alkoxy group having 1 to 4 carbon atoms, and 1 to 4 carbon atoms.
  • halogen atom examples include a chlorine atom, an iodine atom, an iodine atom, and a fluorine atom.
  • the substitution position of the halogen atom is not particularly limited.
  • alkyl group examples include straight-chain or branched ones, and preferably CH 3 , C 2 H 5 or C 3 H 7 .
  • substitution position of the alkyl group is not particularly limited, but is preferably a 3-, 4- or 5-position.
  • haloalkyl group linear or branched, chlorine ⁇ , iodine IS element
  • a hard mouth Gen atoms such as the back MotoHara element and fluorine atoms, the good Mashiku CF 3 It is.
  • the substitution position of the haloalkyl group is not particularly limited.
  • the substitution position of the cyano group is not particularly limited, but is preferably 3- or 4-position.
  • alkoxy group examples include a linear or branched alkoxy group, preferably OCH 3 or OC 2 H 5 .
  • the substitution position of the alkoxy group is not particularly limited, but is preferably a 3-, 4- or 5-position.
  • the haloalkoxy group there may be mentioned a straight or branched, preferably a OCF 3, OC F 2 CH F 2 or OC F 2 CH FC F 3.
  • the g-position of the haloalkoxy group is not particularly limited, but is preferably a 4-position.
  • alkyl group examples include straight-chain or branched ones, and preferably S CH 3 .
  • substitution position of the alkylthio group is not particularly limited, but is preferably the 3-position.
  • substitution position of the amino group is not particularly limited, but is preferably the 3-position.
  • n can be an integer of 1 to 5, preferably 1, 2, 3 or 5.
  • Examples of the compound (1) include those obtained by combining the above-mentioned various substituents.
  • Preferred compounds from the viewpoint of medicinal effects are as follows.
  • R 1 is an alkoxy group having 1 to 4 carbon atoms
  • R 2 is an alkyl group having 1 to 4 carbon atoms
  • (R 3 ) is a hydrogen atom.
  • R 1 is an alkoxy group having 1 to 4 carbon atoms
  • R 2 is an alkyl group having 1 to 4 carbon atoms
  • (R 3 ) ⁇ is a halogen atom.
  • R ′ is an alkynyl group having 3 to 5 carbon atoms
  • R 2 is an alkynyl group having 1 to 4 carbon atoms
  • (R 3 ) ⁇ is a halogen atom.
  • R 1 is an alkoxyalkyl group having 2 to 5 carbon atoms
  • R 2 is an alkyl group having 1 to 4 carbon atoms
  • (R 3 ) ⁇ is a halogen atom.
  • R 1 is 1-4 alkoxy group having a carbon number
  • R 2 is alkyl Le group number ⁇ to 4 carbons
  • (R 3) ⁇ is an alkyl group of one to four carbon atoms some stuff.
  • R 1 is an alkoxy group having 1 to 4 carbon atoms
  • R 2 is an alkyl group having 1 to 4 carbon atoms
  • (R 3 ) ⁇ is a haloalkyl group having 1 to 4 carbon atoms.
  • R ' is ⁇ Li alkynyl group having 3-5 carbons
  • R 2 is alkyl Le group having 1 to 4 carbon
  • (R 3) ⁇ is C 1-4 haloalkyl group having a carbon What is.
  • R 1 is an alkoxyalkyl group number 2-5 carbons
  • 8 2 is 1 to 4 alkyl groups having a carbon number
  • (R 3) eta is a haloalkyl group having ⁇ to 4 carbons some stuff.
  • R 1 is an alkoxy group having 1 to 4 carbon atoms
  • R 2 is an alkyl group having 1 to 4 carbon atoms
  • (R 3 ) ⁇ is a cyano group.
  • R 1 is an alkoxy group having 1 to 4 carbon atoms
  • R 2 is an alkyl group having 1 to 4 carbon atoms
  • (R 3 ) ⁇ is an alkoxy group having 1 to 4 carbon atoms.
  • R 1 is a hydrogen atom
  • R 2 is an alkyl group having 1 to 4 carbon atoms
  • R 1 is an alkenyl group having 3 to 5 carbon atoms
  • R 2 is an alkyl group having 1 to 4 carbon atoms
  • (R 3 ) n is an alkoxy group having 1 to 4 carbon atoms.
  • R 1 is an alkynyl group having 3 to 5 carbon atoms
  • R 2 is an alkyl group having 1 to 4 carbon atoms
  • (R 3 ) ⁇ is an alkoxy group having 1 to 4 carbon atoms thing.
  • R 1 is an alkoxyalkyl group having 2 to 5 carbon atoms
  • R 2 is an alkyl group having 1 to 4 carbon atoms
  • (R 3 ) ⁇ is an alkoxy group having 4 to 4 carbon atoms thing.
  • (R 3 ) ⁇ is alkoxy having 1 to 4 carbons.
  • R 1 is an alkoxy group having 1 to 4 carbon atoms
  • R 2 is an alkyl group having 1 to 4 carbon atoms
  • (R 3 ) ⁇ is a haloalkoxy group having 1 to 4 carbon atoms.
  • R 1 is an alkynyl group having 3 to 5 carbon atoms
  • R 2 is an alkynyl group having 1 to 4 carbon atoms
  • (R 3 ) ⁇ is a haloalkoxy group having 1 to 4 carbon atoms.
  • R 1 is an alkoxy group having 1 to 4 carbon atoms
  • R 2 is an alkyl group having 1 to 4 carbon atoms
  • (R 3 ) is an alkylthio group.
  • R ′ is an alkoxy group having 1 to 4 carbon atoms
  • R 2 is an alkyl group having 1 to 4 carbon atoms
  • (R 3 ). Are the two groups.
  • Preferred specific examples of these compounds (1) are compounds 1, 3, 5, 6, 8 to 14, 16, 16, 18 to 21, 23, 25 to 25 shown in Table 1 below. 27, 29-33, 35-37, 39-45, 47, 49, 51, 53, 55, 57-62 and 64.
  • Compound (1) can be synthesized by the following synthesis methods 1 to 3.
  • Synthesis method 1 Compound (1-1a) (compound (1) in which R 1 is a hydrogen atom) is produced by reacting compound (2) with compound (3) in a solvent as shown below. This reaction can be accelerated in the presence of a base.
  • R 1 , R 2 , R 3 , n and X are as described above.
  • the reaction step is usually performed in the presence of a solvent and a base.
  • the type of the solvent is not particularly limited as long as it does not directly participate in the reaction, and examples thereof include alcohols such as isopropanol, t-butanol, and diethylene glycol; and ketones such as acetone, methyl ethyl ketone, and cyclohexanone.
  • Aliphatic hydrocarbons such as n-hexane and cyclohexane; ethers such as getyl ether, diisopropyl ether, tetrahydrofuran, and dichlorohexane; dichloroethane, chloroform, carbon tetrachloride, tetra Halogenated hydrocarbons such as chloroethane; aromatic hydrocarbons such as benzene, chlorobenzene, toluene, xylene; ditolyls such as acetonitrile and propionitrile; dimethylformamide, dimethylsulfoxide And polar solvents such as sulfolane; and A mixture of these solvents and the like can be mentioned.
  • the amount of the compound (2) and the compound (3) to be used is preferably in a molar ratio of (1:10) to (10: 1), and more preferably (1: 3) to (3: 1). Range.
  • the amount of the solvent used may be such that the compound (3) is used in an amount of 0.1 to 80% by weight; preferably 0.1 to 40% by weight.
  • an inorganic base and an organic base can be used, and an organic base is preferable.
  • Examples of the inorganic base include sodium carbonate, potassium carbonate, calcium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, calcium hydroxide, and other alkaline metal or alkaline earth metal carbonates. And hydroxides; and hydrides of alkali metals such as lithium hydride and sodium hydride.
  • organic base examples include alkoxides of alkali metal atoms such as sodium methoxide and potassium t-butoxide, getylamine, triethylamine, and pyridine.
  • the amount of the base to be used is 0.01 to 5 moles, preferably 0.8 to 2 moles, per 1 mole of Compound (3).
  • the reaction temperature is in the range from 140 to the boiling point of the solvent used, preferably from 0 to 7.
  • the reaction time varies depending on the above-mentioned concentration and temperature, but is usually 0.5 to 24 hours, preferably 1 to 10 hours.
  • Compound (2) can be synthesized according to the method described in JP-A-6-340607.
  • the compound (3) can be obtained by reacting an amide with a sulfur-containing reagent (eg, pentasulfide or Lawson's reagent) according to the method described in JP-A-6-92929.
  • a sulfur-containing reagent eg, pentasulfide or Lawson's reagent
  • the target compound ( ⁇ ⁇ a) shown in Table 1 described below produced as described above is subjected to ordinary post-treatments such as extraction, leaching, filtration and the like. It can be appropriately purified by known means such as recrystallization and various types of chromatography.
  • R 1 ′, R 2 , R 3 , n, X and Y are as defined above.
  • the type of the solvent is not particularly limited as long as it does not directly participate in the present reaction, and examples thereof include those described in Synthesis Method 1.
  • Use of the solvent S can be used such that the amount of the compound ( ⁇ a) is from 0.1 to 80% by weight; preferably, from 0.1 to 40% by weight.
  • Examples of the base include those described in Synthetic Method 1, and are preferably inorganic bases.
  • the amount of the base used is 0.001 to 5 times mol based on compound (1-a), 0.8 to 2 moles is preferable.
  • the reaction temperature is in the range of from 140 ° C to the boiling point of the solvent to be used, preferably from 110 to 70 ° C.
  • the catalyst examples include benzyl triethylammonium chloride and ⁇ -butylammonium bromide tetral.
  • the amount of the catalyst to be used is from ⁇ to 20% by weight, preferably from 3 to 10% by weight, based on the weight of compound (1-a).
  • the reaction time varies depending on the above-mentioned concentration and temperature, but is usually from instant to 12 hours, preferably 0.5 to 8 hours.
  • the target compound (1 -b) produced as described in Table 1 below is subjected to ordinary post-treatments such as extraction, concentration, and filtration, and then re-used as necessary. It can be appropriately purified by known means such as crystals and various types of chromatography.
  • Compound (1-1c) (compound in which R 1 in compound (1) is an alkoxy group having 1 to 4 carbon atoms) is prepared by compound (3) and compound (5) in a solvent as shown below. It can be produced by reacting. This reaction is facilitated by the presence of a base.
  • R′R 2 , R 3 , n and X are as defined above.
  • the type of the solvent is not particularly limited as long as it does not directly participate in the present reaction, and examples thereof include those described in Synthesis Method 1.
  • the amounts of compound (5) and compound (3) used are preferably in a molar ratio of (1:10) to (10: 1), more preferably ( ⁇ : 3) to (3: ⁇ ). Range.
  • the solvent may be used in such an amount that the compound (5) is contained in an amount of 0.1 to 80% by weight; preferably 0.1 to 40% by weight.
  • Examples of the base include those described in Synthesis Method II, and are preferably organic bases.
  • the amount of the base to be used is 001 to 5 moles, preferably 0.8 to 2 moles, relative to compound (5).
  • the reaction temperature is in the range of from 40 ° C to the boiling point of the solvent used, preferably from 110 to 70 ° C.
  • the reaction time varies depending on the above-mentioned concentration and temperature, but is usually 0.5 to 24 hours, preferably ⁇ to 10 hours.
  • Compound (5) can be converted to N-2-methylphenylhydroxylamine through 2-toluene toluene according to the method described in JP-A-6-340607, for example, as shown below.
  • CI C0 2 R 2 (wherein, R 2 has the same meaning as defined above) in which after the reaction in the presence of a base, such as by O- alkyl turned into alkyl halides, with further N- halosuccinimide
  • NCS N-chlorosuccinimide
  • NBS N-promosuccinimide
  • the target compound (11-C) shown in Table 1 described below, produced as described above is subjected to ordinary post-treatments such as extraction, concentration, filtration, and the like, if necessary. It can be appropriately purified by known means such as crystals and various types of chromatography. (Effect of controlling pathogenic bacteria)
  • Examples of the pathogens of agriculture in which the compound (1) of the present invention has a controlling effect include rice blast, cucumber and disease, barley powdery mildew, wheat leaf rust and the like.
  • the agricultural and horticultural fungicide of the present invention contains at least one compound (1) as an active ingredient.
  • the compound (1) can be used alone, but it is usually compounded with a carrier, a surfactant, a dispersant, an auxiliary agent and the like (for example, powders, emulsions, fine granules, granules, water, etc.). Prepared as a composition such as a wetting agent, an oily suspension, or an aerosol).
  • Carriers include, for example, solid carriers such as talc, bentonite, clay, kaolin, cadmium earth, white carbon, vermiculite, slaked lime, cake sand, ammonium sulfate and urea; hydrocarbons (kerosene, mineral oil, etc.), aromatics Hydrocarbons (benzene, toluene, xylene, etc.), chlorinated hydrocarbons (chloroform, carbon tetrachloride, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, cyclohexanone, isophorone, etc.) ), Liquid carriers such as esters (ethyl acetate, ethylene glycol acetate, dibutyl maleate, etc.), alcohols (methanol, n-hexanol, ethylene glycol, etc.), polar solvents (dimethylformamide, dimethyl sulfoxide, etc.)
  • surfactants and dispersants that can be used to improve the performance of this drug, such as adhesion to animals and plants, improved absorption, sensitivity of drugs, emulsification, and spreading, include alcohol sulfates and alkyls. Sulfonates, ligninsulfonates, polyoxyethylene render alcohols and the like can be mentioned. And the properties of the formulation For improvement, for example, carboxymethylcellulose, polyethylene glycol, gum arabic and the like can be used as adjuvants.
  • the above-mentioned carrier, surfactant, dispersant, and auxiliary can be used alone or in appropriate combination, respectively, according to the respective purposes.
  • the active ingredient is usually 1 to 50% by weight for emulsions, usually 0.3 to 25% by weight for powders, usually 1 to 90% by weight for wettable powders, and 1 to 90% by weight for granules. It is usually 0.5 to 10% by weight, for oils it is usually 0.5 to 5% by weight, and for azole it is usually 0.5 "to 5% by weight.
  • Toxanone (trade name; manufactured by Sanyo Chemical Industries, Ltd.) (10 parts by weight) was added to 20 parts by weight of Yidani-Daizotsu 58 and 70 parts by weight of xylene, mixed uniformly, and dissolved to obtain an emulsion.
  • Control efficacy test for cucumber and disease (preventive effect)
  • One cucumber (cultivar: Sagami Hanjiro) is grown per pot in a 6 cm diameter plastic flowerpot, and a 1.5-leaf seedling contains an acetone solution of the active ingredient compound and a surfactant. 0.05%) A drug diluted to a predetermined concentration with water was sprayed at 20 ml per pot.
  • the plants were cultivated in a glass greenhouse for 2 days, and then cucumber and zoospores were prepared from the diseased leaves, and the whole plant was inoculated by spraying on the reverse surface of the leaves.
  • the plants were kept in the dark for 2 days at 2 CTC for 1 day, and then grown in a glass greenhouse for 5 days.
  • the control rate was calculated from the lesion area of the treated plot and the untreated plot.
  • Control value is based on the percent control (%) are shown in Table 2, in 6 steps of 0 to 5 £
  • the plants were cultivated in a glass greenhouse for 2 days, and the conidia suspension of rice blast fungus was uniformly inoculated into the leaves of the plants by spraying.
  • the drug effect was determined by comparing the degree of the lesion in the untreated section with the control value standard described in the above (1).
  • a 10-year-old barley (cultivar: wheat) is grown in a plastic flowerpot with a diameter of 6 cm per pot, and an acetone solution of the active ingredient compound is surface-active on 1.5-leaf seedlings.
  • the plants were cultivated in a glass greenhouse for 2 days, and then the congeners of the congenium of the powdery mildew powdery mildew were collected from the diseased leaves and sprinkled evenly over the plants to inoculate them.
  • the drug effect was determined by comparing the degree of the lesion in the untreated plot with the control value standard described in the above (1).
  • the plants were cultivated for 2 days in a glass greenhouse, and then a suspension of spores of Fusarium head blight was uniformly inoculated by atomization. After inoculation, they were grown in a glass greenhouse for 10 days, and the degree of leaf rust spots of wheat on the first leaf was investigated.
  • the drug effect was determined by comparing the degree of the lesion in the untreated plot with the control value standard described in the above (1).
  • the N-phenyl carbamate compound of the present invention exhibits an excellent bactericidal action against rice blast fungus, cucumber fungus, barley powdery mildew, wheat rust, etc., and is useful as a fungicide for agriculture and horticulture. It is something.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • 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)
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  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des composés de N-phénylcarbamate représentés par la formule (1). Dans cette formule, R1 représente un atome d'hydrogène, un groupe alcoxy comportant 1 à 4 atomes de carbone, un groupe alkyle comportant 1 à 4 atomes de carbone, un groupe alcynyle ayant 3 à 5 atomes de carbone, un groupe alcoxyalkyle ayant 2 à 5 atomes de carbone, un groupe alcényle possédant 3 à 5 atomes de carbone, ou -CO¿2?R?4 où R4¿ représente un groupe alkyle ayant 1 à 4 atomes de carbone; R2 représente un groupe alkyle ayant 1 à 4 atomes de carbone, R3 représente un atome d'hydrogène, un atome d'halogène, un groupe alkyle ayant 1 à 4 atomes de carbone, un groupe haloalkyle ayant 1 à 4 atomes de carbone, un groupe cyano, un groupe alcoxy ayant 1 à 4 atomes de carbone, un groupe haloalcoxy présentant 1 à 4 atomes de carbone, un groupe alkylthio avec 1 à 4 atomes de carbone ou un groupe nitro; et n est un nombre entier compris entre 1 et 5.
PCT/JP1997/002417 1996-07-12 1997-07-11 Composes de n-phenylcarbamate, procede de preparation de ces composes et bactericides agricoles et horticoles WO1998002414A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP8183502A JPH1025278A (ja) 1996-07-12 1996-07-12 Ｎ−フェニルカーバメート化合物、その製法及び農園芸用の殺菌剤
JP8/183502 1996-07-12

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Publication number Priority date Publication date Assignee Title
EP1178036A1 (fr) * 2000-08-04 2002-02-06 Aventis Cropscience S.A. Dérivés de phénylimidates fongicides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05170726A (ja) * 1991-02-07 1993-07-09 Ishihara Sangyo Kaisha Ltd Ｎ−フェニルカーバメート系化合物、それらの製造方法及びそれらを含有する有害生物防除剤
JPH06340607A (ja) * 1993-04-04 1994-12-13 Nippon Nohyaku Co Ltd Ｎ−置換フェニルカルバミン酸誘導体及びその製造方法並びに農園芸用殺菌剤
JPH07502747A (ja) * 1992-01-29 1995-03-23 ビーエーエスエフ　アクチェンゲゼルシャフト カルバメートおよびそれらを含む作物保護剤

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05170726A (ja) * 1991-02-07 1993-07-09 Ishihara Sangyo Kaisha Ltd Ｎ−フェニルカーバメート系化合物、それらの製造方法及びそれらを含有する有害生物防除剤
JPH07502747A (ja) * 1992-01-29 1995-03-23 ビーエーエスエフ　アクチェンゲゼルシャフト カルバメートおよびそれらを含む作物保護剤
JPH06340607A (ja) * 1993-04-04 1994-12-13 Nippon Nohyaku Co Ltd Ｎ−置換フェニルカルバミン酸誘導体及びその製造方法並びに農園芸用殺菌剤

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