WO1995011226A1 - Derives de benzene substitues, leur procede de production et compositions biocides les contenant destinees a la lutte contre des organismes nuisibles - Google Patents

Derives de benzene substitues, leur procede de production et compositions biocides les contenant destinees a la lutte contre des organismes nuisibles Download PDF

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WO1995011226A1
WO1995011226A1 PCT/JP1994/001711 JP9401711W WO9511226A1 WO 1995011226 A1 WO1995011226 A1 WO 1995011226A1 JP 9401711 W JP9401711 W JP 9401711W WO 9511226 A1 WO9511226 A1 WO 9511226A1
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group
substituted
compound
alkoxy
aryl
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PCT/JP1994/001711
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English (en)
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Hisaya Nishide
Shigeru Mitani
Minako Inoue
Kanako Nakano
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Ishihara Sangyo Kaisha Ltd.
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Priority to AU78630/94A priority Critical patent/AU7863094A/en
Publication of WO1995011226A1 publication Critical patent/WO1995011226A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • 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
    • A01N47/02—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 no bond to a nitrogen atom
    • A01N47/06—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 no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • 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
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/54—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
    • C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/44—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
    • C07C329/02—Monothiocarbonic acids; Derivatives thereof
    • C07C329/04—Esters of monothiocarbonic acids
    • C07C329/06—Esters of monothiocarbonic acids having sulfur atoms of thiocarbonic groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C333/02—Monothiocarbamic acids; Derivatives thereof
    • C07C333/04—Monothiocarbamic acids; Derivatives thereof having nitrogen atoms of thiocarbamic groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/96—Esters of carbonic or haloformic acids

Definitions

  • the present invention relates to substituted benzene derivatives, processes for their production, biocidal compositions for control of harmful organisms containing them as active ingredients and intermediates thereof.
  • carbamate compounds derived from physostigmine have been practically used as insecticides. These carbamate insecticides are nervous system distracting agents having acetylcholine esterase inhibitory
  • the compounds of the present invention are different in the chemical structure from these carbamate compounds.
  • substituted benzene derivatives having a certain specific structure such as a carbamate, carbonate or thiocarbamate structure, exhibit excellent biocidal activities against harmful organisms.
  • the present invention has been accomplished on the basis of this discovery.
  • the present invention provides a substituted benzene derivative of the formula (I)
  • A is an aryloxy group which may be substituted, an arylthio group which may be substituted or
  • R 1 and R 2 which are independent of each other is an alkyl group which may be substituted, or an aryl group which may be substituted, n is 1 or 2
  • B is a halogen atom, an alkyl group, an aryl group, an alkoxy group, a cycloalkyl group, a cycloalkyloxy group, a haloalkyl group, a haloalkyloxy group, a cyano group or a nitro group
  • m is an integer of from 0 to 4
  • X is an oxygen atom or a sulfur atom
  • Y is an alkoxy group, an alkylthio group, an amino group, an alkylamino group or a dialkylamino group, processes for its production, a biocidal composition for control of harmful organisms containing it as an active ingredient, and an
  • the aryl moiety or the aryl group for A, B or each of R 1 and R 2 in the formula (I) includes, for example, phenyl, pyridyl, thienyl, furanyl, pyrrolyl, pyrazolyl, imidazolyl, indanyl, pirazinyl, isoxazolyl and
  • the substituents for the aryloxy group which may be substituted or the arylthio group which may be substituted in the definition of A or for the aryl group which may be substituted in the definition of each of R 1 and R 2 include, for example, halogen atoms; C 1-4 alkyl groups which may be substituted by halogen or C 1-4 alkoxy; aryl groups which may be substituted by halogen or C 1-4 alkoxy; a nitro group; a cyano group; C 1-4 alkoxy groups which may be substituted by halogen; C 1-4
  • alkylthio groups an amino group; di-C 1-4 alkylamino groups; and methylenedioxy groups which may be
  • the number of substituents may be one or more, and when the number of substituents is more than one, the plurality of substituents may be the same or different.
  • the alkyl group which may be substituted in the definition of each of R 1 and R 2 may be a C 1-6 linear or branched alkyl group, such as methyl, ethyl, propyl, butyl, pentyl or hexyl. Its substituents include, for example, halogen atoms; a cyano group; C 1-4 alkoxy groups; and C 1-4 alkylthio groups.
  • the number of substituents may be one or more, and when the number of substituents is more than, one, the plurality of
  • the halogen atom, the halogen atom in the haloalkyl or haloalkyloxy group, or the halogen atom constituting a substituent includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • the alkyl group or the alkyl moiety in each of the alkoxy group, the haloalkyl group or the haloalkyloxy group may be a C 1-6 linear or branched alkyl group.
  • the cycloalkyl group or the cycloalkyl moiety in the cycloalkyloxy group may be the one having from 3 to 8 carbon atoms.
  • substituents defined by B when m is two or more, the plurality of the substituents may be the same or different.
  • the alkyl moiety in each of the alkoxy group, the alkylthio group, the alkylamino group and the dialkylamino group may be a C 1-8 linear or branched alkyl group. Further, in the case of the dialkylamino group, the number of carbon atoms in the two alkyl moieties may be the same or different.
  • R 1 and R 2 substituted, for each of R 1 and R 2 , or the aryl group for B, is phenyl, pyridyl, thienyl, furanyl, pirrolyl, pirazolyl, imidazolyl, indanyl, pyrazinyl, isooxazolyl or isothiazolyl; the aryloxy group which may be substituted, or the arylthio group which may be substituted, for A, or the aryl group which may be substituted for each of R 1 and R 2 , may have one or more substituents selected from the group consisting of halogen atoms; C 1-4 alkyl groups which may be substituted by halogen or C 1-4 alkoxy; aryl groups which may be substituted by halogen or C 1-4 alkoxy; a nitro group; a cyano group; C 1-4 alkoxy groups which may be substituted by halogen; C 1-4 alkylthio groups; an amino
  • halogen provided that when the number of substituents is more than one, the plurality of substituents may be the same or different; and the alkyl group which may be substituted, for each of R 1 and R 2 , may have one or more substituents selected from the group consisting of halogen atoms; a cyano group; C 1-4 alkoxy groups; and C 1-4 alkylthio groups.
  • a substituted benzene derivative of the formula (I), wherein A is -ON C(R 1 )R 2 wherein R 1 and R 2 are as defined above, X is an oxygen atom, n is 1, and m is 0.
  • the substituted benzene derivative of the formula (I) can be produced by the following method (A) or (B).
  • Y 1 is an alkoxy group, an alkylthio group or a dialkylamino group, and Hal is a halogen atom.
  • Method (A) is carried out usually in the presence of a solvent and a base.
  • the solvent may, for example, be an aromatic hydrocarbon such as benzene, toluene, xylene or chlorobenzene; a halogenated aliphatic hydrocarbon such as chloroform, carbon tetrachloride, methylene chloride, dichloroethane or trichloroethane; a cyclic or non-cyclic aliphatic hydrocarbon such as n-hexane or cyclohexane; an ether such as diethyl ether, dioxane or tetrahydrofuran; a ketone such as acetone, methyl ethyl ketone or methyl isobutyl ketone; a nitrile such as acetonitrile or propionitrile; or an aprotic polar solvent such as dimethylformamide, N-methyl-2- pyrrolidone, dimethylsulfox
  • the base may be an inorganic base or an organic base.
  • the inorganic base may, for example, be an alkali metal hydroxide such as sodium hydroxide or potassium
  • the organic base may, for example, be pyridine, triethylamine or diisopropylethylamine.
  • the reaction temperature is usually from -20°C to the boiling point of the solvent, preferably from 0 to 50°C, and the reaction time is usually from 0.5 to 24 hours.
  • M-OCN represents a cyanate
  • M is an alkali metal
  • R represents an isocyanate, and R is an alkyl group.
  • Method (B) is carried out usually in the presence of a solvent.
  • a catalyst may be used.
  • the solvent may be the same as used for the above-mentioned method (A).
  • the catalyst may, for example, be an acid such as boron trifluoride, hydrochloric acid, aluminum chloride, an alkyltin chloride or an alkyltin acetate, or a base such as triethylamine, pyridine, dimethylaniline, dimethylaminopyridine, 1,4-diazabicyclo(2,2,2)octane, N-piperidine or sodium acetate.
  • the reaction temperature is usually from -20°C to the boiling point of the
  • reaction time is usually from 0.5 to 24 hours.
  • the compound of the formula (II) can be prepared, for example, by the following reactions (C) to (E).
  • Ar represents an aryl group which may be substituted.
  • Method (C) can be carried out by acetylating two OH groups in substituted or unsubstituted saligenin, followed by the reaction with a compound of the formula (V-1), (V-2) or (V-3) and a base such as sodium hydride or butyl lithium, to obtain an alkali metal salt.
  • the reaction is conducted in the presence of a solvent.
  • the solvent may be the same as used in the above method (A).
  • the reaction temperature is usually from -20°C to the boiling point of the solvent, and the reaction time is usually from 0.5 to 24 hours.
  • A, B and m are as defined above, and R is an alkyl group.
  • the compound of the formula (II-4) can be prepared by the five step reactions.
  • substituted or unsubstituted thiosalicylic acid is reacted with protecting agents.
  • the carboxyl group of the thiosalicylic acid is esterified with an alcohol such as methanol
  • the SH group of this esterified product is converted to sulfide with dihydropyran.
  • the respective reactions can be conducted under the conditions commonly employed for the esterification and the sulfide-conversion, respectively.
  • the third step is a reduction of the carbonyl group of this sulfide compound.
  • a reducing agent such as lithium aluminum hydride is applied.
  • the reaction condition may be the one commonly used.
  • the fourth step is a condensation reaction of the substituent A of this reduced product. This reaction can be accomplished by the following method.
  • the above reaction is carried out in the presence of a solvent as well as an alkyl or aryl phosphine such as tributyl phosphine and an azocarboxylic acid ester such as diethyl azodicarboxylate.
  • the solvent may be the same as used in the above-mentioned method (A).
  • the reaction temperature is usually from -78°C to +70°C, and the reaction time is usually from 0.5 to 24 hours.
  • the fifth step is a reaction for removing the
  • iodine is employed for this reaction.
  • the reaction proceeds at room temperature, whereby a dimer of the compound of the formula (II-4) is formed by a disulfide bond and then converted by a reducing agent such as lithium aluminum hydride to the compound of the formula (II-4).
  • a reducing agent such as lithium aluminum hydride
  • silver nitrate or the like may be employed to convert it to silver mercaptide, whereupon the tetrahydropyranyl group is removed, followed by hydrolysis with weak acid, to obtain the free compound of the formula (II-4).
  • A, B and m are as defined above, and R is an alkyl group.
  • the compound of the above formula (II-5) can be prepared by the five step reactions.
  • substituted or unsubstituted O-hydroxyphenylacetic acid is protected with appropriate masking group, respectively.
  • the carboxyl group is esterified in the same manner as in the above-mentioned thiosalicylic acid
  • the OH group of this esterified product is etherified with benzyl bromide.
  • the reaction condition for this etherification reaction may be that one commonly used.
  • the third step is a reduction of the carbonyl group of this etherified product, and the same method as in the third step of the above-mentioned method (D) may be employed.
  • the fourth step is a condensation reaction of the substituent A. This reaction can be accomplished by the following method.
  • a compound of the formula (IV-3) is once reacted with p-toluenesulfonyl chloride or methanesulfonyl chloride in order to make it leaving group, in the presence of a base such as triethylamine and a solvent, to obtain a tosylate or mesylate of the compound of the formula (IV-3).
  • a base such as triethylamine and a solvent
  • the tosylate or mesylate of the compound of the formula (IV-3) is reacted with a compound obtained by reacting a compound of the formula (V-1), (V-2) or (V-3) with sodium hydride or butyl lithium, in the presence of a solvent.
  • the solvent to be used for this reaction may be the same as used in the above-mentioned method (A).
  • the reaction temperature is usually from -20°C to the boiling point of the
  • reaction time is usually from 0.5 to 24 hours.
  • the fifth step is a reaction for removing the benzyl group.
  • palladium-carbon or platinum oxide may, for example, be used as the catalyst, and by stirring under a hydrogen atmosphere, the compound of the formula (II-5) can readily be obtained.
  • the compound of the formula (I) according to the present invention is useful as an active ingredient of biocidal compositions for control of harmful organisms.
  • the compound of the formula (I) can be used as the active ingredient of agricultural and
  • horticultural fungicides to exhibit an excellent effect of controlling plant diseases such as rice blast, rice sheath blight, rice helminthosporium leaf spot, cucumber anthracnose, cucumber powdery mildew, cucumber downy mildew, tomato late blight, tomato early blight, citrus melanose, citrus common green mold, apple and pear scab, apple alternaria blotch, grape downy mildew, and gray mold, sclerotinia rot and rust of various crops; and soil diseases caused by phytopathogenic fungi such as
  • the compound of the formula (I) exhibits an especially excellent effect of controlling rice blast, powdery mildew of various crops, gray mold of various crops, sclerotinia rot of various crops, cucumber and grape downy mildew, and tomato and potato late blights.
  • the compound of the present invention exhibits not only a long-term residual effect and an excellent preventive effect, but also has a curative effect to enable disease control to be effected through treatment therewith after infection. Furthermore, disease control is possible through soil treatment with the compound of the present invention.
  • the compound of the present invention is effective not only against sensitive strains but also against various resistant strains such as Benomyl-resistant powdery mildew, Metalaxyl-resistant downy mildew, and Benomyl-and/or dicarboximide-resistant gray mold.
  • the compound of the present invention has an
  • the compound of the present invention may be used in combination with an adjuvant((s) to prepare various formulations such as an emulsifiable concentrate, a dust, a wettable powder, an aqueous solution, granules, a suspension concentrate, etc. like in the case of
  • the adjuvant there can be mentioned carriers, emulsifying agents, suspending agents, dispersants, spreaders, penetrating agents, wetting agents, thickening agents, and stabilizing agents, which may be appropriately added to the compound of the present invention as desired.
  • Carriers are classified into solid carriers and liquid carriers.
  • solid carriers include animal or vegetable powders such as starch, sugar, cellulose powder, cyclodextrin, activated carbon, soybean powder, wheat powder, chaff powder, wood powder, fish powder, and powdery milk; and mineral powders such as talc, kaolin, bentonite, bentonite-alkylamine complex, calcium carbonate, calcium sulfate, sodium bicarbonate, zeolite, diatomaceous earth, white carbon, clay, alumina, silica, and sulfur powder.
  • animal or vegetable powders such as starch, sugar, cellulose powder, cyclodextrin, activated carbon, soybean powder, wheat powder, chaff powder, wood powder, fish powder, and powdery milk
  • mineral powders such as talc, kaolin, bentonite, bentonite-alkylamine complex, calcium carbonate, calcium sulfate, sodium bicarbonate, zeolite, diatomaceous earth, white carbon, clay,
  • liquid carriers examples include water; animal or vegetable oils such as soybean oil, cotton seed oil, and corn oil; alcohols such as ethyl alcohol and ethylene glycol; ketones such as acetone and methyl ethyl ketone; ethers such as dioxane and tetrahydrofuran; aliphatic hydrocarbons such as kerosine, lamp oil, and liquid paraffin; aromatics, phenols, phenols, phenolsulfate, ethylene glycol, ethylene glycol, ketone, ethers such as dioxane and tetrahydrofuran; aliphatic hydrocarbons such as kerosine, lamp oil, and liquid paraffin; aromatic
  • hydrocarbons such as xylene, trimethylbenzene,
  • halogenated hydrocarbons such as chloroform and
  • chlorobenzene acid amides such as dimethylformamide
  • esters such as ethyl acetate and fatty acid glycerin esters; nitriles such as acetonitrile; sulfur-containing compounds such as dimethylsulfoxide; and N-methoxypyrrolidone.
  • the suitable blending weight ratio of the compound of the present invention to the adjuvant(s) is generally in the range of 0.05:99.95 to 90:10, and preferably in the range of 0.2:99.8 to 80:20.
  • the concentration of the compound of the present invention at the time of application varies depending on the crop as the object of application treatment, the way of application, the form of a formulation, the dose, etc., and hence cannot be generically determined.
  • the concentration of the compound of the present invention as the active ingredient may usually be in the range of 0.1 to 10,000 ppm, and preferably in the range of 1 to 2,000 ppm.
  • the dose may usually be in the range of 10 to 100,000 g/ha
  • biocidal composition of the present invention for control of harmful organisms, which
  • the above components are uniformly mixed to obtain a wettable powder.
  • the above components are uniformly mixed to obtain a dust.
  • the above components are mixed and finely pulverized to obtain an aqueous suspension concentrate.
  • the compound of the present invention may be used in mixture or combination with other agricultural chemical(s), examples of which include insecticides, acaricides, nematocides, fungicides, antiviral agents, attractants, herbicides, and plant growth regulators. in this case, the effect of the compound or biocidal
  • composition of the present invention may sometimes be enhanced.
  • active ingredients of such insecticides, acaricides or nematocides include the following compounds:
  • O-ethyl O-(4-nitrophenyl)phenyl phosphonothioate (common name: EPN)
  • O,O-diethyl O-(2-isopropyl-6-methylpyrimidin-4- yl)phosphorothioate (common name: Diazinon)
  • the compound of the present invention may also be used in mixture or combination with microbial
  • agricultural chemicals such as B.T. and insect viruses
  • antibiotics such as avermectin and milbemycin.
  • active ingredients of the aforementioned fungicides include the following
  • Maneb ethylenebis (dithiocarbamate (Maneb) (common name: Mancozeb),
  • cupric hydroxide (common name: cupric hydroxide), and copper 8-quinolinolate (common name: Oxine-Copper); Isoxazole compounds
  • triphenyltin hydroxide (common name: Fentin
  • triphenyltin acetate (common name: Fentin Acetate); Urea compounds
  • fungicides include anthraquinone compounds, crotonic acid copmounds and antibiotics.
  • the suitable blending weight ratio of the substituted benzene derivative of the present invention represented by the formula (I) to the other agricultural chemical(s) when used in mixture or combination may generally be in the range of 1:300 to 300:1, and preferably in the range of 1:100 to 100:1.
  • Example 5 (6) and 0.44 g (4.36 mmol) of triethylamine were dissolved in 25 ml of dry acetonitrile, and 0.41 g (4.36 mmol) of methyl chlorocarbonate was added thereto under cooling with ice. The mixture was stirred
  • the area, number or length of lesions is less than 10% of that in the non-treated plot.
  • the area, number or length of lesions is less than 40% of that in the non-treated plot.
  • the area, number or length of lesions is less than 70% of that in the non-treated plot.
  • polyethylene pot having a diameter of 7.5 cm.
  • the pot was kept in a constant-temperature chamber at 22 to 24°C for about 24 hours, after which the cucumber was dusted and inoculated with conidia of fungi of powdery mildew (Sphaerotheca fuliginea).
  • the area of lesions on the first leaf was examined to find a rating as the index of control according to the above- mentioned criteria for evaluation. The results were as follows.
  • Compound No. 1 exhibited a rating of 4 as the index of control at a concentration of 500 ppm and Compound No. 4 exhibited a rating of 5 as the index of control at a concentration of 250 ppm.
  • polyethylene pot having a diameter of 7.5 cm.
  • the pot was kept in a constant-temperature chamber at 22 to 24°C for about 24 hours, after which the cucumber was sprayed and
  • Rice plant (cultivar: Koshihirakri) was cultivated in a polyethylene pot having a diameter of 7.5 cm. When the rice plant reached a four-leaf stage, it was sprayed with 20 ml of a solution having a predetermined active
  • the pot was kept in a constant-temperature chamber at 22 to 24°C for about 24 hours, after which the rice plant was sprayed and inoculated with a spore suspension of fungi of blast (Pyricularia oryzae). Fifth to seventh day after the inoculation, the number of lesions was examined to find a rating as the index of control according to the aforementioned criteria for evaluation.
  • Compound Nos. 1 and 9 exhibited a rating of 5 as the index of at a concentration of 500 ppm and Compound Nos. 11, 19 and 22 exhibited a rating of 4 as the index of control at a concentration of 500 ppm.
  • Tomato (cultivar: Ponderosa) was cultivated in a polyethylene pot having a diameter of 7.5 cm. When the tomato reached a four-leaf stage, it was sprayed with 10 ml of a solution having a predetermined active ingredient concentration through a spray gun. The pot was kept in a constant-temperature chamber at 22 to 24°C for about 24 hours, after which the tomato plant was sprayed and inoculated with a zoosporangia suspension of fungi of late blight (Phytophthora infestans). Third to fourth day after the inoculation, the area of lesions was examined to find a rating as the index of control according to the aforementioned criteria for evaluation.
  • Compound Nos. 6, 9 and 10 exhibited a rating of 5 as the index of control at a concentration of 500 ppm and Compound Nos. 22, 24 and 25 exhibited a rating of 4 as the index of control at a concentration of 500 ppm.
  • polyethylene pot having a diameter of 7.5 cm.
  • the pot was kept in a constant-temperature chamber at 22 to 24°C for about 24 hours, after which the first leaf was inoculated with a spore suspension of fungi of Benomyl- and dicarboximide-sensitive gray mold (Botrytis cinerea) in a potato glucose broth.
  • the length of lesions was examined to find a rating as the index of control according to the above-mentioned
  • Compound Nos. 7, 17 and 18 exhibited a rating of 5 as the index of control at a concentration of 500 ppm, and Compound Nos. 3 and 8 exhibited a rating of 4 as the index of control at a concentration of 500 ppm.
  • An aqueous dispersion containing from 25 to 200 ppm of Compound No. 17, 18 or 23 and from 25 to 200 ppm of Fluazinam or Chlorophthalonil, as active ingredients, is applied to the locus of plants such as cucumber, egg plant and grape, where gray mold is infested, whereby the growth of the gray mold is excellently controlled.

Abstract

Dérivé de benzène substitué de formule (I) dans laquelle A représente un groupe aryloxy qui peut être substitué, un groupe arylthio qui peut être substitué ou -ON=C(R?1)R2, R1 et R2¿ étant chacun indépendamment l'un de l'autre un groupe alkyle qui peut être substitué, ou un groupe aryle qui peut être substitué, n représente 1 ou 2, B représente un atome d'halogène, un groupe alkyle, un groupe aryle, un groupe alcoxy, un groupe cycloalkyle, un groupe cycloalkyloxy, un groupe haloalkyle, un groupe haloalkyloxy, un groupe cyano ou un groupe nitro, m représente un nombre entier de 0 à 4, X représente un atome d'oxygène ou un atome de soufre et Y représente un groupe alcoxy, un groupe alkylthio, un groupe amino, un groupe alkylamino ou un groupe dialkylamino.
PCT/JP1994/001711 1993-10-20 1994-10-13 Derives de benzene substitues, leur procede de production et compositions biocides les contenant destinees a la lutte contre des organismes nuisibles WO1995011226A1 (fr)

Priority Applications (1)

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AU78630/94A AU7863094A (en) 1993-10-20 1994-10-13 Substituted benzene derivatives, processes for their production and biocidal composition for control of harmful organisms containing them

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JP5/285602 1993-10-20
JP28560293 1993-10-20

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CN105814024A (zh) * 2013-12-12 2016-07-27 住友化学株式会社 芳族化合物及其用途
US11426412B2 (en) 2017-10-18 2022-08-30 Jubilant Epipad LLC Imidazo-pyridine compounds as PAD inhibitors
US11459338B2 (en) 2017-11-24 2022-10-04 Jubilant Episcribe Llc Heterocyclic compounds as PRMT5 inhibitors
US11529341B2 (en) 2018-03-13 2022-12-20 Jubilant Prodel LLC Bicyclic compounds as inhibitors of PD1/PD-L1 interaction/activation
US11629135B2 (en) 2017-11-06 2023-04-18 Jubilant Prodell Llc Pyrimidine derivatives as inhibitors of PD1/PD-L1 activation
US11833156B2 (en) 2017-09-22 2023-12-05 Jubilant Epipad LLC Heterocyclic compounds as pad inhibitors

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105814024A (zh) * 2013-12-12 2016-07-27 住友化学株式会社 芳族化合物及其用途
EP3081559A4 (fr) * 2013-12-12 2017-10-04 Sumitomo Chemical Company, Limited Composé aromatique et son application
US11833156B2 (en) 2017-09-22 2023-12-05 Jubilant Epipad LLC Heterocyclic compounds as pad inhibitors
US11426412B2 (en) 2017-10-18 2022-08-30 Jubilant Epipad LLC Imidazo-pyridine compounds as PAD inhibitors
US11629135B2 (en) 2017-11-06 2023-04-18 Jubilant Prodell Llc Pyrimidine derivatives as inhibitors of PD1/PD-L1 activation
US11459338B2 (en) 2017-11-24 2022-10-04 Jubilant Episcribe Llc Heterocyclic compounds as PRMT5 inhibitors
US11529341B2 (en) 2018-03-13 2022-12-20 Jubilant Prodel LLC Bicyclic compounds as inhibitors of PD1/PD-L1 interaction/activation

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JPH07179402A (ja) 1995-07-18

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