WO2002092584A1 - Derives du thiadiazole, pesticides a usage agricole et horticole, et leurs utilisations - Google Patents

Derives du thiadiazole, pesticides a usage agricole et horticole, et leurs utilisations Download PDF

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Publication number
WO2002092584A1
WO2002092584A1 PCT/JP2002/004592 JP0204592W WO02092584A1 WO 2002092584 A1 WO2002092584 A1 WO 2002092584A1 JP 0204592 W JP0204592 W JP 0204592W WO 02092584 A1 WO02092584 A1 WO 02092584A1
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group
alkyl
alkylamino
halo
different
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PCT/JP2002/004592
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English (en)
Japanese (ja)
Inventor
Hayami Nakao
Yoshihiro Matsuzaki
Masanori Tohnishi
Masayuki Morimoto
Shinsuke Fujioka
Tsuyoshi Takemoto
Koki Mamezuka
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Nihon Nohyaku Co., Ltd.
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Publication of WO2002092584A1 publication Critical patent/WO2002092584A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero 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
    • A01N47/08—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
    • 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/32—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing >N—CO—N< or >N—CS—N< groups directly attached to a cycloaliphatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to a thiaziazole derivative, an agricultural and horticultural drug containing the compound as an active ingredient, and a method for using the same.
  • the present inventors have conducted intensive studies to develop a novel agricultural and horticultural drug.
  • the thiadiazole derivative represented by the general formula (I) of the present invention is a novel compound not described in any literature,
  • the present invention has been found to be useful as a drug, specifically an insecticide, acaricide, fungicide, and herbicide, and has completed the present invention.
  • the present invention provides a compound represented by the general formula (I)
  • R is a hydrogen atom, a cyano group, a nitro group, a -C 6 alkyl group, a C 3 -C 6 cycloalkyl group, which may be the same or different, a -C 6 alkoxy group, a mono C 6 alkyl amino group, It represents a substituted-alkyl group having one or more substituents selected from di-alkylamino groups which may be the same or different, or a C 6 alkoxycarbonyl group.
  • Y is a halogen atom, c r c 6 alkyl group, Nono b c r c 6 alkyl group, - c 6 alkylthio O group, or phenoxy substituted halo CfCg alkyl group group, C 3 -C 6 Shikuroarukinore group, halo C 3 - C 6 cycloalkyl group, _ (6 alkoxy group, halo ( ⁇ C 6 alkoxy group, Cf C 6 alkylthio group, Nono b (: ⁇ C 6 alkylthio group, C r C 6 alkylsulfinyl group, Nono b C ⁇ C 6 alkylsulfinyl group, - C 6 alkylsulfonyl group, halo d-c 6 Al alkylsulfonyl group, mono c r c 6 alkylamino group, the same or different and may di - C 6 alkylamino group, mono
  • A is the formula (II) (In the formula, X 1 , X 2 , X 3 , and X 4 may be the same or different, and may be a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C r C 6 alkyl group, a halo CfCe alkyl group, a C 3- C 6 cycloalkyl group, Nono b c 3 - c 6 cycloalkyl group, c 6 alkoxy group, Nono b c r c 6 alkoxy group, C r C 6 alkylthio group, Nono b C ⁇ C 6 alkylthio group, (: ⁇ c 6 Arukirusurufu Iniru group, Nono b C r C 6 alkyl sulfide el group, ( ⁇ c 6 alkylsulfonyl group, Nono port (: ⁇ alkylsulfonyl group, a
  • V is Cf C 6 alkyl groups, halo ( ⁇ c 6 alkyl group, - c 6 alkoxy group, halo - C 6 alkoxy group, a mono - c 6 alkylamino group, the same or different and may di - C 6 alkylamino group, monohalo - c 6 alkyl amino groups, the same or different and may dihalo CFC 6 alkylamino group, c r c 6 alkoxy c r c 6 Al kill group, halo C -Ce alkoxy ( ⁇ _ (: 6 alkyl, - C 6 alkylthio - C 6 alkyl group, C port c r c 6 alkylthio c ⁇ c 6 alkyl group, c t - c 6 alkyls
  • U is hydrogen atom, an alkyl group, a halo c r c 8 alkyl group, c 2 - c 8 alkenyl group, Nono b C 2 _C 8 alkenyl group, C 3 - C 5 alkynyl group, Nono b C 3 -C 5 alkynyl group , c 6 ⁇ Norekokishi C ⁇ Ce alkyl group, Nono b C ⁇ C 6 alkoxy - C 6 alkyl group, - C 6 alkylene thioether CFC 6 alkyl group, Nono b - c 6 alkylthio c ⁇ c 6 alkyl group, c 6 alkyl Rusurufieru c r c 6 alkyl group, Nono b c r c 6 alkylsulfinyl cc 6 alkyl group, C r C 6 alkylsulfonyl - ⁇ alkyl group, halo C, -
  • Z represents an oxygen atom or a sulfur atom.
  • the present invention relates to a thiadiazole derivative represented by the formula (I), an agricultural and horticultural drug containing the compound as an active ingredient, and a method for using the same.
  • halogen atom represents a chlorine atom, bromine atom, iodine atom or fluorine atom
  • n ⁇ represents normal
  • ⁇ s ⁇ Indicates a secondary one
  • ⁇ t -J indicates a tertiary one
  • C Factory C 6 alkyl means, for example, methinole, ethyl, n-propyl, i-propyl, n-butyl, i-butinole, s-butinole, t one Puchinore, n- Penchinore, neopentyl Le, shows a linear or branched chain carbon atoms 1-6 alkyl groups hexyl, etc., to n-, "halo C r C 6 alkyl” are the same or A straight-chain or branched alkyl group having 1 to 6 carbon atoms, which is
  • C 2 -C 8 alkenyl refers to a linear or branched chain having one or more double bonds such as bur, aryl, 2-buteninole, 3-butul, prenyl, and 4,6-octactenyl. 2 to 2 carbon atoms
  • C 3 -C 5 alkynyl is a straight-chain or branched-chain carbon atom having one or more triple bonds such as 2 propyl, 2-butynyl, and 3-pentynyl. Shows the number 3 to 5 alkynyl groups.
  • heterocyclic group refers to a 5- or 6-membered heterocyclic group having at least one heteroatom selected from an oxygen atom, a sulfur atom or a nitrogen atom, such as a pyridyl group, a pyridine-N-oxide group, Pyrimidinyl group, furyl group, tetrahydrofuryl group, chenyl group, tetrahydrochenyl group, tetrahydroviranyl group, tetrahydrothiopyranyl group, oxazolyl group, isoxazolyl group, oxaziazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, thiadiazolyl group Examples thereof include a triazolyl group and a pyrazolyl group.
  • the thiadiazole derivative represented by the general formula (I) of the present invention may contain one or more asymmetric carbon atoms or asymmetric centers in its structural formula, and may contain two or more optical isomers and In some cases, diastereomers may be present, and the present invention includes all optical isomers and mixtures including them in any ratio.
  • the thiadiazole derivative represented by the general formula (I) of the present invention may have two kinds of geometric isomers derived from a carbon-carbon double bond in the structure in the structure in some cases. It is intended to include all geometric isomers and mixtures containing them in any proportion.
  • Z is preferably an oxygen atom
  • R is preferably a hydrogen atom
  • Y is (C) C 6 alkyl is preferred
  • W is preferably a carbon atom
  • X 1 is a halogen atom
  • X 2 is preferably a hydrogen atom
  • X 3 is preferably a halogen atom
  • X 4 is preferably a hydrogen atom
  • T is 1 O—, one S-, preferably, U is c r c 8 alkyl group, halo c r 3 ⁇ 4 alkyl group, C r C 8 alkenyl group, halo C FCG alkenyl good Good.
  • the fungicide, Z is preferably an oxygen atom
  • R represents a hydrogen atom
  • Y is (Nono port) C r C 6 alkyl are preferred
  • W is preferably a carbon atom
  • ⁇ x 4 is a hydrogen atom, a halogen atom, - c 6 alkyl group is preferable, tau is - s-, one
  • Z is preferably an oxygen atom
  • R is preferably a hydrogen atom
  • C r C 6 alkyl is preferable
  • Y is preferably a C 6 alkyl
  • W is preferably a carbon atom
  • X 1 is preferably a halogen atom.
  • X 2 is preferably a hydrogen atom
  • X 3 is a hydrogen atom, preferably halogen atom
  • X 4 is preferably a hydrogen atom
  • T is one S-, -SO-, one S_ ⁇ 2 one preferably, U is c r c 8 alkyl group, halo c r c 8 alkyl group, c r c 8 alkenyl group, c 3 - c 5 alkynyl group.
  • the thiadiazole derivative represented by the general formula (1) of the present invention can be produced, for example, by the production method shown below.
  • T is one O—, one S—, one SO—, One S 0 2 —, one CH 2 —, and U is the same as above.
  • the aromatic carboxylic acid derivative represented by the general formula (IV) is reacted with the 2-aminothiadiazole represented by the general formula (V) using a condensing agent or the like in the presence of an inert solvent and a base.
  • a thiadiazole derivative represented by the general formula (1-1) can be produced.
  • the condensing agent used in this reaction include getyl cyanophosphate (DEPC), carbodidiimidazolone (CDI), 1,3-dihexyl hexyl carbodiimide (DCC), and chlorinated esternoles. And 2-chloro-1-methylpyridinium iodide.
  • Examples of the base used in this reaction include an inorganic base and an organic base.
  • Examples of the inorganic base include hydroxides of alkali metal atoms such as sodium hydroxide and hydroxylating hydride, sodium hydride, and hydrogenating hydride.
  • Alkali metal hydrides such as alkali metal salts of alcohols such as sodium methoxide and potassium butoxide, sodium carbonate, carbonate lime, carbonates such as sodium hydrogen carbonate, and organic bases such as triethylamine, Pyridine, DBU and the like can be exemplified, and the amount of the pyridine and DBU used may be selected from the range of equimolar to excess molar with respect to the aromatic carboxylic acid derivative represented by the general formula (IV).
  • the inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene, methylene chloride, chloroform, and carbon tetrachloride.
  • Halogenated hydrocarbons such as benzene, dichlorobenzene, etc., chain or cyclic ethers such as getyl ether, dioxane and tetrahydrofuran, and esters such as ethyl acetate Amides such as dimethylformamide and dimethylacetamide; dimethylsulfoxide; 1,3-dimethyl-2-imidazolidinone; and inert solvents such as acetone and methylethylketone.
  • the inert solvents can be used alone or as a mixture of two or more.
  • each reactant may be used in an equimolar amount.However, any of the reactants can be used in excess, and the reaction temperature is from room temperature to the boiling point of the inert solvent used.
  • the reaction time is not constant depending on the reaction scale and the reaction temperature, and may be in the range of several minutes to 48 hours.
  • the desired product may be isolated from the reaction system containing the desired product by a conventional method. If necessary, the desired product can be produced by recrystallization, purification by column chromatography, or the like.
  • the aromatic carboxylic acid derivative represented by the general formula (IV) is converted into a halogenated acyl derivative (VI) by using a halogenating agent or the like in the presence or absence of an inert solvent, thereby obtaining the halogenated acyl derivative.
  • a halogenating agent or the like By isolating (VI) or not isolating and reacting the aminothiadiazole derivative represented by the general formula (V) with a base or the like in the presence of an inert solvent, the compound represented by the general formula (1) -1) Thiadiazole derivative represented by 1.)
  • General formula (IV) ⁇ General formula (VI)
  • halogenating agent used in this reaction examples include, for example, halogenating agents such as thionyl chloride, phosphorus oxychloride, trichlorine ichlin, phosphorus tribromide, phosphorus oxybromide, and dichloromethyl methyl ether.
  • the amount may be appropriately selected and used from the range of 1 to 100 equivalents to the aromatic carboxylic acid derivative represented by the general formula (IV).
  • the inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene, methylene chloride, chloroform, and carbon tetrachloride. And inert solvents such as halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene and the like, and esters such as ethyl acetate and the like. They can be used alone or as a mixture of two or more.
  • aromatic hydrocarbons such as benzene, toluene, and xylene, methylene chloride, chloroform, and carbon tetrachloride.
  • inert solvents such as halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene and the like, and esters such as ethyl acetate and the like. They can be used alone or as a mixture of two or more.
  • the reaction can be carried out at a temperature from room temperature to the boiling point of the inert solvent to be used.
  • the reaction time is not fixed depending on the reaction scale and the reaction temperature, but may be within a range from several minutes to 48 hours. After completion of the reaction, it can be isolated from the reaction system containing the desired product by a conventional method or used without isolation for the next reaction.
  • the bases or inert solvents exemplified in Production Method 1 can be used as the base or inert solvent used in this reaction.
  • each reactant may be used in an equimolar amount.However, any of the reactants can be used in excess, and the reaction temperature is from room temperature to the boiling point of the inert solvent used.
  • the reaction time may be varied within a range of several minutes to 48 hours, which varies depending on the reaction scale and the reaction temperature.
  • the desired product may be isolated from the reaction system containing the desired product by a conventional method, and the desired product may be produced by recrystallization, column chromatography or the like, if necessary.
  • This reaction can be carried out according to Production method 1 or 2.
  • the reduction method that can be used in this reaction includes a conventional method for reducing a nitro group, for example, a method using a metal such as iron, zinc, or tin and an acid such as formic acid, acetic acid, or hydrochloric acid as a reducing agent, Raney nickel in a hydrogen atmosphere, A method using palladium, platinum, or the like can be given.
  • the inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction.
  • examples thereof include alcohols such as methanol, ethanol, and 2-propanol, tetrahydrofuran, dioxane, and 1,2-dimethyloxetane.
  • Ethers formic acid, acetic acid, propionic acid, hydrochloric acid and other acids, and inert solvents such as water. These inert solvents can be used alone or in combination of two or more. .
  • the reaction can be carried out at a temperature ranging from room temperature to the boiling point of the inert solvent used.
  • the reaction time is not fixed depending on the reaction scale and the reaction temperature, but may be carried out within a range from several minutes to 48 hours.
  • acylating agent used in this reaction examples include acid halides such as diacetylacetyl and benzoyl chloride, and halogenated carbonates such as methyl methyl carbonate, ethyl ethyl carbonate and phenyl ethyl carbonate. be able to.
  • the amino group is modified by using a halogenated carbamic acid such as dimethyl benzoyl amide or diphenyl carbamoyl oxysulfide, or an isocyanate such as methyl isocyanate, ethyl isocyanate or phenyl isocyanate. You can also.
  • Examples of the base used in this reaction include an inorganic base and an organic base.
  • hydroxides of alkali metal atoms such as sodium hydroxide and hydroxylating power
  • hydrides of alkali metals such as sodium hydride and hydrogenating power
  • alcohols such as sodium ethoxide, potassium t-butoxide
  • Examples of carbonates such as potassium metal salt, sodium carbonate, carbonated carbonate, sodium hydrogencarbonate and the like
  • organic bases include, for example, triethylamine, pyridine, DBU and the like.
  • the inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction.
  • aromatic hydrocarbons such as benzene, toluene, and xylene, methylene chloride, chloroform, and tetrachloride.
  • Halogenated hydrocarbons such as arsenic carbon, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, ethers such as tetrahydrofuran, dioxane, 1,2-dimethoxyethane, and esters such as ethyl acetate And the like.
  • ethers such as tetrahydrofuran, dioxane, 1,2-dimethoxyethane
  • esters such as ethyl acetate And the like.
  • each reactant may be used in an equimolar amount.However, any of the reactants can be used in excess, and the reaction temperature is from room temperature to the boiling point of the inert solvent used.
  • the reaction time is not constant depending on the reaction scale and the reaction temperature, and may be in the range of several minutes to 48 hours.
  • the desired product may be isolated from the reaction system containing the desired product by a conventional method. If necessary, the desired product can be produced by recrystallization, purification by column chromatography, or the like.
  • the aromatic carboxylic acid derivative represented by the general formula (IV) can be produced according to a conventional method or a known method, for example, a method illustrated below.
  • the compound (IV-3) in which Q is represented by ⁇ U can be obtained by a conventional method, for example, by converting the hydroxycarboxylic acid derivative (IV-2) to ethanol.
  • the ester CEX) is treated with an alkyl halide in the presence of a base, for example, by heating in an alcoholic solvent such as sulfuric acid and borane trifluorofluoride getyl etherate in the presence of an acid catalyst.
  • an ether compound (IX-1) can be produced, and the ether compound ( ⁇ - ⁇ ) can be hydrolyzed by a conventional method, for example, using sodium hydroxide or the like.
  • the compound (IV-5) in which Q is SU is, for example, an aminocarboxylic acid derivative represented by the general formula (IV-4).
  • X J. Chem. So Perkin Trans. 1, p385 (1984)
  • X reduced to thiol by a conventional method, alkylated by various alkylation methods, and then hydrolyzed.
  • the compound (IV-5) in which Q is represented by SU is, for example, a hydroxycarboxylic acid derivative represented by the general formula (IX).
  • the aminothiadiazole derivative represented by the general formula (V) can be synthesized according to a known method (J. Het. Chem., 3336 (1966)).
  • cPr represents a cyclopropyl group
  • cPen represents a cyclopentyl group
  • c_Hex represents a cyclohexyl group
  • Ph represents a phenyl group
  • Pyd represents pyridyl.
  • P yz is a pyrazolyl group
  • Th i is a phenyl group Is shown.
  • the thiadiazole derivative represented by the general formula (I) of the present invention exhibits pest control activity, for example, insecticidal activity, acaricidal activity, fungicidal activity, and herbicidal activity, and can be used as an agricultural and horticultural drug.
  • Agricultural and horticultural chemicals containing the thiadiazole derivative represented by the general formula (I) of the present invention as an active ingredient are suitable for paddy rice, fruit trees, vegetables, other crops and flowers. It is suitable for controlling various pests such as agriculture, forestry, horticulture, stored grain pests, sanitary pests and nematodes.
  • insecticides or acaricides for agricultural and horticultural use
  • various pests such as agriculture, forestry, horticulture, stored grain pests, sanitary pests and nematodes.
  • Adoxophyes orana fasciata Adoxophyes sp.
  • Gusarecentiyu Pratylenchus coffeae
  • Lingual cysts Glabodera rostchiensis
  • Nekobu sensuyu Meloidogyne sp.
  • Mirenunesenchyu Tylenchulus
  • Agricultural and horticultural chemicals containing the thiadiazole derivative represented by the general formula (I) of the present invention as an active ingredient and in particular, agricultural and horticultural fungicides can be broadly classified as filamentous fungal diseases, for example, incomplete fungi (for example, Botrytis spp., Helminthosporium spp., Fusarium spp., Septoria spp., Sarcospora spp., Pyricularia spp. Alterna spp.
  • incomplete fungi for example, Botrytis spp., Helminthosporium spp., Fusarium spp., Septoria spp., Sarcospora spp., Pyricularia spp. Alterna spp.
  • Basidiomycetes eg, Hemileia genus disease, Rhizoctonia genus, Puccinia genus disease, etc.
  • Ascomycetes eg, Venturia genus disease, Podosphaera
  • Genus disease Erysiphe genus disease, Monilinia genus disease
  • Pensinula Unsinul
  • fungi eg, diseases of the genus Ascochyta, diseases of the genus Phoma, diseases of the genus Pythium, diseases of the genus Corticium, diseases of the genus Pyrenophora, etc. It can be used to control diseases and the like.
  • fungi eg, diseases of the genus Ascochyta, diseases of the genus Phoma, diseases of the genus Pythium, diseases of the genus Corticium, diseases of the genus Pyrenophora, etc.
  • Individual diseases include, for example, rice blast (Pyricularia oryzae), rice rhizoctonia solani (Rhizoctonia solani) ⁇ rice leaf defoliation (Cochiobolus raiyabeanus), rice seedling wilt ;! Hei (Rhizopus chinensis, Pythium graminicola, Fusarium) graminicola, Fusarium roseum, Mucor sp., Phoma sp., Tricoderma sp.), rice messy disease (Gibberella fujikuroi), oats and wheat.
  • Agricultural and horticultural chemicals containing the thiadiazole derivative represented by the general formula (I) of the present invention as an active ingredient particularly herbicides for agricultural and horticultural use include, for example, barnyardgrass (first-year grassy grass, paddy field pests), tamagayari (potassium japonicus) Family annual grass, paddy field weeds), pine trees (perennial grasses of the scrophulariaceae family, swamps, waterways, paddy fields, perennial grasses of paddy fields), ⁇ ⁇ (perfume family, paddy fields, wetlands, wetlands, ditch) Grass), Firefly (perenniaceous perennial grass, paddy field, swamp, ditch), Sparrow butterfly (grass weed, paddy field, low swamp), Emberk (grass annual, grassland, wasteland, field) Occurrence), Artemisia (Asteraceae perennial grass, Occurs in the mountains and fields), Meishishiba (Gramineae annuals,
  • Agricultural and horticultural agents particularly agricultural and horticultural insecticides, acaricides, fungicides, herbicides, and the like, which comprise the thiadiazole derivative represented by the general formula (1) of the present invention as an active ingredient, include paddy crops and upland crops.
  • the agricultural and horticultural drug of the present invention is generally used after being formulated into a convenient form according to a conventional method for agricultural chemical formulation.
  • the thiadiazole derivatives represented by the general formula (I) are dissolved, separated, suspended, mixed, and impregnated by mixing them in a suitable inert carrier or, if necessary, together with an auxiliary in a suitable ratio. It may be adsorbed or adhered and formulated into an appropriate dosage form, for example, a suspension, emulsion, liquid, wettable powder, wettable powder, granule, powder, tablet, pack or the like.
  • the inert carrier that can be used in the present invention may be either solid or liquid.
  • the material that can be a solid carrier include soybean flour, cereal flour, wood flour, bark flour, saw flour, and tobacco stem flour.
  • Silicas ⁇ eg diatomaceous earth, silica sand, mica, white carbon (Synthetic high-dispersion silicic acid also called hydrous fine silicon powder and hydrous silicic acid, some of which contain calcium silicate as a main component depending on the product.) ⁇
  • Activated carbon iodine powder, Inorganic mineral powders such as pumice, calcined diatomaceous earth, crushed bricks, fly ash, sand, calcium carbonate, calcium
  • the material that can be a liquid carrier is selected from those having a solvent function per se and those capable of dispersing the active ingredient compound with the aid of an adjuvant even without the solvent function.
  • the following carriers can be exemplified, and these are used alone or in the form of a mixture of two or more kinds, for example, water, alcohols (eg, For example, methanol, ethanol, isopropanol, butanol, ethylene glycol, etc., ketones (eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), ethers (Eg, ethyl ether, dioxane, cellosolve, dipropinole ethereol, tetrahydrofuran, etc.), aliphatic hydrocarbons (eg, kerosene, mineral oil, etc.), aromatic hydrocarbons (eg, benzen
  • Examples of the other adjuvants include the following representative adjuvants. These adjuvants are used according to the purpose, and may be used alone or in combination of two or more kinds. In some cases, it is possible to use no auxiliaries at all.
  • Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and Z or wetting the active ingredient compounds, such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene higher fatty acid ester, polyoxyethylene resin
  • surfactants such as acid esters, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfonates, naphthalene sulfonic acid condensates, lignin sulfonates, and higher alcohol sulfate esters can do.
  • auxiliaries For the purpose of stabilizing the dispersion of the active ingredient compound, adhering and / or binding, the following auxiliaries may be used.
  • auxiliaries such as noresenorelose, gum arabic, polyvinylinoleanol, pine oil, bran oil, bentonite, and ligninsulfonate can also be used.
  • adjuvants can be used to improve the flowability of the solid product.
  • adjuvants such as Pettas, stearates, and alkyl phosphates can be used.
  • a peptizer for the suspension product for example, a naphthalene sulfonic acid condensate, a condensed phosphate or the like may be used.
  • an antifoaming agent for example, an auxiliary agent such as silicone oil can be used.
  • an auxiliary agent such as silicone oil
  • preservatives 1,2-benzisothiazolin-3-one, parachlorometa-xylenol, butyl benzoate and the like can also be added.
  • a functional spreading agent such as a metabolic decomposition inhibitor such as piperonyl butoxide, an antifreezing agent such as propylene glycol, an antioxidant such as BHT, an ultraviolet absorber, and the like. Additives can also be added.
  • the compounding ratio of the active ingredient compound can be adjusted as necessary, and it can be appropriately selected and used from the range of 0.01 to 90 parts by weight in 100 parts by weight of the agricultural and horticultural insecticide.
  • the weight is 0.01 to 50 weight. /.
  • the content is preferably from 0.01 to 50% by weight.
  • the agricultural and horticultural insecticide, acaricide, fungicide, and herbicide of the present invention are used for controlling various pests, diseases, and weeds, or they are appropriately diluted or suspended with water or the like to control pests.
  • An effective amount may be applied to crops where the occurrence of the pest, disease, or weed is predicted or where the occurrence is not preferred.
  • the amount of the agricultural and horticultural agent used in the present invention depends on various factors, for example, the purpose, target pests, crop growth status, pests, diseases, weed occurrence tendency, weather, environmental conditions, dosage form, application method, application place, Although it fluctuates depending on the application time, etc., the active ingredient compound may be appropriately selected from the range of 0.001 g to 10 kg per 10 ares, preferably 0.01 g to 1 kg according to the purpose. Good.
  • the agricultural and horticultural chemicals of the present invention may further contain other agricultural and horticultural insecticides, acaricides, nematicides, and the like for the purpose of extending pests and diseases to be controlled, diseases, weeds, suitable periods for controlling, or reducing the amount of drugs. It can be used in combination with fungicides, herbicides, biological pesticides, etc., and can also be used in combination with plant growth regulators, fertilizers, etc., depending on the application.
  • Other agricultural and horticultural insecticides, acaricides, and nematicides used for such purposes include, for example, ethion, trich-mouth norehon, metamidophos, acephate, dichlorvos, mevinfos, monocrotophos, malathion, dimethate, honoremothion.
  • Examples of agricultural and horticultural fungicides used for the same purpose include sulfur, lime-sulfur mixture, and Copper sulfate, iprobenphos, edifenphos, tolcophos methyl, chiram, polycarbamate, zineb, manzeb, mancozeb, provevineb, thiophanate, thiophanate methyl, benomyl, iminoctadine acetate, iminoctazin albesylate, mepronil, Flutolanil, penciclon, flametopinole, tifluzamide, metalaxyl, oxadixyl, carpropamide, diclofluanide, phnoresnoreffamide, chlorothaloninole, kresoxime 'methyl, phenoxanil (NNF-9425), ehoxanol Zole, Fluorimide, Procymidone, Vinclozolin, Iprodione,
  • nuclear polyhedrosis virus NPV
  • granulosis virus GV
  • cytoplasmic polyhedrosis virus NPV
  • NPV nuclear polyhedrosis virus
  • GV granulosis virus
  • cytoplasmic polyhedrosis virus NPV
  • NPV nuclear polyhedrosis virus
  • GV granulosis virus
  • cytoplasmic polyhedrosis virus cytoplasmic polyhedrosis virus
  • Trichoderma lignolan a microbial pesticide used as an insecticide or nematicide such as (Steinernema carpocapsae), Stana ' ⁇ Steinernema kushidai, Pasteuria' Pasteuria penetrans', etc.
  • Agrobacterium radiobactor non-pathogenic Erwinia carotovora (Erwinia carotovora), microbial pesticides used as bactericides such as Bacillus subtilis (Bacillus subtilis), and herbicides such as Zanthomonas campestris Similar effects can be expected by mixing and using biological pesticides to be used.
  • biopesticides for example, Encarsia formosa, Coleman: Aphidius colemani, Aphidoletes aphidimyza), Isyah dime (Diglyphus isaea), Nomomogli imayunochi (Dacnusa sibirica), chili cabridina (Phytoseiulus persimilis), Kucumeri liskabridani (Amblyseius cucumeris) The Beauveria 'Beauveria
  • At least 10 parts of a mixture with calcium alkylbenzenesulfonate is uniformly mixed and dissolved to form an emulsion.
  • Test example 1 Insecticidal test against Japanese moth (Plutella xylostella)
  • the adult Chinese moth is released to Chinese cabbage seedlings to lay eggs. Two days after the release, Chinese cabbage seedlings with spawning eggs are treated with 50% of the drugs containing the compounds listed in Tables 1 to 5 as active ingredients.
  • Test Example 2 Acaricidal test against Namihadani (Tetranychus urticae)
  • a leaf disc having a diameter of 2 cm was prepared from the leaf of a wing, and placed on a wet filter paper, inoculated with a female adult, and diluted with a turntable at 500 ppm to prepare the compounds described in Tables 1 to 5.
  • 5 Oml of a drug solution as an active ingredient was evenly sprayed, and after spraying, allowed to stand in a constant temperature room at 25 ° C. Two days after drug treatment, the number of surviving and dead insects was examined.
  • Test Example 3 Test of herbicidal effect on paddy field weeds before emergence
  • Test example 4 Control test against tomato blight
  • Three leaf tomato (cultivar: Pontelosa), which was prepared by diluting a drug containing the compound of the present invention shown in Tables 1 to 5 as an active ingredient prepared according to the formulation example with water to a predetermined concentration and cultivating in a pot Foliage.
  • a zoospore suspension of Phytophthora infestans was sprayed and inoculated.
  • Five days after inoculation the degree of disease on each leaf was examined.
  • Test example 5 Control test for apple scab
  • the compounds containing the compounds of the present invention described in Tables 1 to 5 as active ingredients prepared according to the formulation examples were diluted to a predetermined concentration with water, and the foliage was added to apple seedlings (variety: Wang Lin) cultivated in pots. Sprayed. One day after spraying, a conidia suspension of apple scab (Venturia inaequalis) was spray-inoculated. Two weeks after the inoculation, the disease incidence of each leaf was examined.

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

Abstract

L'invention porte sur des dérivés du thiadiazole de formule générale (I), sur des pesticides à usage agricole et horticole contenant lesdits dérivés comme principe actif, et sur leurs utilisations. Dans la formule (I) R est H, cyano, nitro, C1-6 alkyle, C3-6 cycloalkyle, C1-6 alkyle substitué, ou analogues; Y est halogéno, C1-6 alkyle, C1-6 haloalkyle, ou analogues; Z est O ou S; A est un groupe représenté par la formule (II); W est C ou N; et Q est T-U (T étant -O-, -S-, -CH2-, ou analogues; et U est H, C1-6 alkyle, ou analogues).
PCT/JP2002/004592 2001-05-14 2002-05-13 Derives du thiadiazole, pesticides a usage agricole et horticole, et leurs utilisations WO2002092584A1 (fr)

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JP2014510088A (ja) * 2011-03-22 2014-04-24 バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー Ｎ−（１，３，４−オキサジアゾール−２−イル）アリールカルボキサミドおよび除草剤としてのその使用
US8846727B2 (en) 2009-05-12 2014-09-30 Romark Laboratories, L.C. Haloalkyl heteroaryl benzamide compounds
US8895752B2 (en) 2007-08-03 2014-11-25 Romark Laboratories L.C. Alkylsulfonyl-substituted thiazolide compounds
US9023877B2 (en) 2009-06-26 2015-05-05 Romark Laboratories L.C. Compounds and methods for treating influenza
WO2015117912A1 (fr) * 2014-02-07 2015-08-13 Syngenta Participations Ag Dérivés d'amide pesticidement actifs comportant des substituants contenant du soufre
WO2016087265A1 (fr) * 2014-12-01 2016-06-09 Syngenta Participations Ag Dérivés amide hétérocycliques actifs à action pesticide comportant des substituants contenant du soufre
WO2016087257A1 (fr) * 2014-12-01 2016-06-09 Syngenta Participations Ag Dérivés amide hétérocycliques à activité pesticide comportant des substituants contenant du soufre
JP2019500365A (ja) * 2015-12-17 2019-01-10 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ ベンズアミド化合物及び除草剤としてのそれらの使用
WO2020254530A1 (fr) 2019-06-18 2020-12-24 Syngenta Crop Protection Ag Dérivés de 7-sulfonyl-n-(1,3,4-thiadiazol-2-yl)-quinoxaline-6-carboxamide et dérivés respectifs de -benzimidazole-5-, -imidazo[4,5-b]pyridine-5-, -3h-furo[3,2b]pyridine-5-, -quinoléine-2- et -naphtalène-2-carboxamide utilisés en tant que pesticides
WO2021153720A1 (fr) * 2020-01-31 2021-08-05 クミアイ化学工業株式会社 Dérivé d'amide d'acide 3-alcoxybenzoïque et agent de lutte contre les nuisibles

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US8895752B2 (en) 2007-08-03 2014-11-25 Romark Laboratories L.C. Alkylsulfonyl-substituted thiazolide compounds
US9126992B2 (en) 2009-05-12 2015-09-08 Romark Laboratories, L.C. Haloalkyl heteroaryl benzamide compounds
US8846727B2 (en) 2009-05-12 2014-09-30 Romark Laboratories, L.C. Haloalkyl heteroaryl benzamide compounds
USRE47786E1 (en) 2009-05-12 2019-12-31 Romark Laboratories L.C. Haloalkyl heteroaryl benzamide compounds
EA021587B1 (ru) * 2009-05-12 2015-07-30 РОМАРК ЛЭБОРЕТЕРИЗ Эл. Си. Соединения галогеналкилгетероарилбензамида
USRE46724E1 (en) 2009-05-12 2018-02-20 Romark Laboratories, L.C. Haloalkyl heteroaryl benzamide compounds
US9820975B2 (en) 2009-06-26 2017-11-21 Romark Laboratories L.C. Compounds and methods for treating influenza
US10912768B2 (en) 2009-06-26 2021-02-09 Romark Laboratories L.C. Compounds and methods for treating influenza
US11850237B2 (en) 2009-06-26 2023-12-26 Romark Laboratories L.C. Compounds and methods for treating influenza
US9023877B2 (en) 2009-06-26 2015-05-05 Romark Laboratories L.C. Compounds and methods for treating influenza
US9345690B2 (en) 2009-06-26 2016-05-24 Romark Laboratories L.C. Compounds and methods for treating influenza
US10363243B2 (en) 2009-06-26 2019-07-30 Romark Laboratories L.C. Compounds and methods for treating influenza
JP2014510088A (ja) * 2011-03-22 2014-04-24 バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー Ｎ−（１，３，４−オキサジアゾール−２−イル）アリールカルボキサミドおよび除草剤としてのその使用
WO2015117912A1 (fr) * 2014-02-07 2015-08-13 Syngenta Participations Ag Dérivés d'amide pesticidement actifs comportant des substituants contenant du soufre
CN107108568A (zh) * 2014-12-01 2017-08-29 先正达参股股份有限公司 具有含硫取代基的杀有害生物活性酰胺杂环衍生物
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JP2018502148A (ja) * 2014-12-01 2018-01-25 シンジェンタ パーティシペーションズ アーゲー 硫黄含有置換基を有する殺有害生物的に活性なアミド複素環式誘導体
CN107108568B (zh) * 2014-12-01 2021-08-10 先正达参股股份有限公司 具有含硫取代基的杀有害生物活性酰胺杂环衍生物
US10494366B2 (en) 2014-12-01 2019-12-03 Syngenta Participations Ag Pesticidally active amide heterocyclic derivatives with sulphur containing substituents
CN107001352A (zh) * 2014-12-01 2017-08-01 先正达参股股份有限公司 具有含硫取代基的杀有害生物活性酰胺杂环衍生物
US10590123B2 (en) 2014-12-01 2020-03-17 Syngenta Participations Ag Pesticidally active amide heterocyclic derivatives with sulphur containing substituents
WO2016087257A1 (fr) * 2014-12-01 2016-06-09 Syngenta Participations Ag Dérivés amide hétérocycliques à activité pesticide comportant des substituants contenant du soufre
WO2016087265A1 (fr) * 2014-12-01 2016-06-09 Syngenta Participations Ag Dérivés amide hétérocycliques actifs à action pesticide comportant des substituants contenant du soufre
CN107001352B (zh) * 2014-12-01 2021-06-04 先正达参股股份有限公司 具有含硫取代基的杀有害生物活性酰胺杂环衍生物
JP2019500365A (ja) * 2015-12-17 2019-01-10 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ ベンズアミド化合物及び除草剤としてのそれらの使用
WO2020254530A1 (fr) 2019-06-18 2020-12-24 Syngenta Crop Protection Ag Dérivés de 7-sulfonyl-n-(1,3,4-thiadiazol-2-yl)-quinoxaline-6-carboxamide et dérivés respectifs de -benzimidazole-5-, -imidazo[4,5-b]pyridine-5-, -3h-furo[3,2b]pyridine-5-, -quinoléine-2- et -naphtalène-2-carboxamide utilisés en tant que pesticides
JPWO2021153720A1 (fr) * 2020-01-31 2021-08-05
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