WO2003084927A1 - Haloalcenes, procede de production et agents de protection phytosanitaire les contenant - Google Patents

Haloalcenes, procede de production et agents de protection phytosanitaire les contenant Download PDF

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Publication number
WO2003084927A1
WO2003084927A1 PCT/JP2003/004331 JP0304331W WO03084927A1 WO 2003084927 A1 WO2003084927 A1 WO 2003084927A1 JP 0304331 W JP0304331 W JP 0304331W WO 03084927 A1 WO03084927 A1 WO 03084927A1
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compound
oxo
heterocyclic group
group
salt
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PCT/JP2003/004331
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English (en)
Japanese (ja)
Inventor
Hiroshi Okada
Masayuki Morita
Tsuyoshi Ueda
Hiromi Takeo
Hidemasa Kominami
Kenichi Nakamoto
Yayoi Yoshida
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Ishihara Sangyo Kaisha, Ltd.
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Priority to AU2003221032A priority Critical patent/AU2003221032A1/en
Publication of WO2003084927A1 publication Critical patent/WO2003084927A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/36—Nitrogen atoms

Definitions

  • Haloalkene compounds methods for their production and pesticides containing them
  • the present invention relates to a novel octaloalkene compound useful as an active ingredient of a pesticidal agent.
  • the present inventors have conducted various studies on halalkane-based compounds to find a better pest control agent. As a result, they have found that a novel haloalkene-based compound has a very high control effect on harmful organisms at a low dose and completed the present invention. That is, the present invention provides a compound of the formula (I):
  • [X 1 and X 2 are each halogen, Y is a hydrogen atom or halogen, and n is
  • Q is 1) chenyl, furyl, pyrrolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiadiazo one
  • halogen in X 1 , X 2 and Y include each atom of fluorine, chlorine, bromine or iodine.
  • the heterocyclic group in Q may have several combinations depending on the position of the hetero atom or the difference of the fused site, but the present invention includes all of them.
  • thiadiazolyl includes 1,2,3-thiadiazolyl and 1,3,4-thiadiazolyl
  • triazolyl includes 1,2,3-triazolyl and 1,2,4-triazolyl.
  • Triazinyl includes 1,2,4_triazinyl and 1,3,5-triazinyl; benzochenil includes benzo [b] phenyl and benzo [c] phenyl;
  • Benzofuranyl includes benzo [b] furanyl and benzo [c] furanyl -
  • Benzoisothiazolyl includes 1,2-benzoisothiazolyl and 2,1-benzoisothiazolyl
  • benzoisoxazolyl includes 1,2-benzoisoxazolyl
  • 2, 1- Benzoisoxazolyl is included
  • benzothiadiazolyl includes 1,2,3-benzothiadiazolyl and 2,1,3-benzothiadiazolyl. The same applies to a partially saturated heterocyclic group, a saturated heterocyclic group, or an oxo or thioxo heterocyclic group.
  • the partially saturated heterocyclic group in Q is obtained by partially hydrogenating the above-mentioned heterocyclic group.
  • the saturated heterocyclic group in Q is one in which the above-mentioned heterocyclic group is completely hydrogenated, and examples thereof include tetrahydrofuranyl, pyrrolidinyl, piberidinyl, piperazinyl, and morpholiel.
  • the oxo or oxo heterocyclic group in Q is the dithiazolyl, oxazinyl, thiazinyl, partially saturated heterocyclic group or a methylene moiety in the saturated heterocyclic group converted to oxo or thioxo, for example, 2-oxotetrahydrophenyl, 2-thiotetrahydrophenyl, 2-oxotetrahydrofuranyl, 2-oxotetrahydrofuranyl, 2-oxotetrahydrofuranyl, 2-oxopyrrolidinyl, 2,5-dioxopyrrolidinyl, 2,4- Dioxothiazolidinyl, 4-oxo-4,5-dihydroxazolyl, 4-oxo-1,4,5-dihydro_1H_imidazole-2-yl, 5-oxo-1 4,5-dihydro-1H —Pyrazolyl, 3-oxo-1,2,3-d
  • the number of the substituents of the heterocyclic group, partially saturated heterocyclic group, saturated heterocyclic group, or oxo or oxo heterocyclic group (all the heterocyclic parts may be substituted) in Q May be 1 or 2 or more. In the case of 2 or more, these substituents may be the same or different.
  • Q examples include for example, halogen, nitro, Shiano, (C ⁇ _ 8) alkyl, C port (Ci 8) alkyl, optionally Ariru portion substituted Ariru (Ci -
  • heteroaryl-alkyl to Heteroariru part may be substituted - 8) alkyl, (C 3 _ 8) cycloalkyl, halo (C 3 _ 8) cycloalkyl, (C 2 one 8) alkenyl, halo (C 2 - 8) Arukeniru, (C 2 one 8) alkynyl, Bruno, mouth (C 2 8) alkynyl, optionally substituted Ariru, Teroariru to but it may also be substituted, -NR 1 R 2, -OR 1 , -SR 1 , -SOR 1 , — S ⁇ 2 R 1 , -SO z NR 1 R 2 , -COR 1 , one C ⁇ 2 R 1 , -COSR 1 , one CSOR 1 , — OCOR 3 ,- CH 2 CN and the like.
  • R 1 and R 2 are each independently a hydrogen atom, (ju- 8 ) alkyl, halo- 8 ) alkyl, aryl (Ci- 8 ) alkyl optionally substituted with aryl, and heteroaryl with aryl. also to be heteroaryl (d - 8) alkyl, (C 3 - 8) cycloalkyl, halo (C 3 _ 8) cycloalkyl, (C 2 8) an alkenyl, halo (C 2 8) Arukeniru, (C 2 8) alkynyl, Nono b (C 2 _ 8) ⁇ Rukiniru, Teroari Lumpur to which may be optionally Ariru or substituted optionally substituted.
  • R 3 is _ 8) alkyl, halo (Ci _ 8) alkyl, Ariru moiety may be substituted Ariru ( ⁇ one 8) alkyl, Heteroariru portion heteroaryl optionally substituted (Ci one 8) alkyl, (C 3 8) cycloalkyl, Bruno, mouth (C 3 8) cycloalkyl, (C 2 _ 8) alkenyl, halo (C 2 _ 8) alkenyl Le, (C 2 8) alkynyl, halo (C 2 _ 8 ) alkynyl, optionally substituted Aryl or an optionally substituted heteroaryl.
  • Hetero ring group in Q heterocyclic group partially saturated, the substituents of the saturated heterocyclic group, Okiso or Chioki Sohetero Hajime Tamaki (heterocyclic moiety to all of the optionally substituted), R 1
  • R 1 Examples of the substituent of the aryl which may be substituted or the substituent of the heteroaryl which may be substituted included in each of R 2 and R 3 include, for example, halogen, nitro, cyano, (Ci 8 ) alkyl, halo (Ci - 8) alkyl, (C 3 -
  • R and R 5 are each independently hydrogen atom, - 8) alkyl, halo (Ci _ 8) alkyl, (C 3 8) cycloalkyl, Bruno, mouth (C 3 - 8) cycloalkyl, (C 2
  • Arukeniru Roh, mouth (C 2 - 8) Arukeniru, is a (C 2 _ 8) alkynyl or halo (C 2 _ 8) alkynyl.
  • aryl or aryl moiety examples include, for example, phenyl, naphthyl, phenanthrenyl, anthracenyl, indenyl, indanyl and the like.
  • heteroaryl or heteroaryl moiety include those similar to the heterocyclic group in the aforementioned Q.
  • the - alkyl or alkyl moiety of 8 may be linear or branched, and specific examples thereof, for example methyl, Echiru, propyl, isopropyl, heptyl, tert-butyl, pentyl, hexyl, heptyl, Okuchiru etc. But It is.
  • C 3 described above - is a specific example of a cycloalkyl or cycloalkyl moiety of 8, such as cyclopropyl, cyclopentyl, cyclohexyl, Petit cyclohexane Le, and the like Shikurookuchiru.
  • C 2 mentioned above - alkenyl or alkenyl moiety of 8 may be linear or branched, and specific examples thereof include vinyl, 1-Purobe alkenyl, Ariru, iso propenyl, 1-butenyl, 1 , 3-butenyl, 1-hexenyl, 1-heptenyl, 4-octenyl and the like.
  • C 2 mentioned above - alkynyl or alkynyl moiety of 8 may be linear or branched, and specific examples thereof, for example Echiniru, 2-heptynyl, 2-pentyl two Le, hexynyl to 3, 4 Jimechiru - 2-pentinyl, 4-octinyl and the like.
  • halogen or the halogen as a substituent include each atom of fluorine, chlorine, bromine or iodine.
  • the number of halogens as a substituent may be 1 or 2 or more. In the case of 2 or more, each halogen may be the same or different.
  • the halogen may be substituted at any position.
  • Examples of the salt of the haloalkene compound represented by the formula (I) include all salts that are agriculturally acceptable, for example, alkali metal salts such as sodium salt and potassium salt; magnesium salt, calcium Alkaline earth metal salts such as salts; ammonium salts such as dimethylamine salts and triethylamine salts; inorganic salts such as hydrochlorides, perchlorates, sulfates, and nitrates; acetates, methanesulfonates Organic acid salts and the like.
  • alkali metal salts such as sodium salt and potassium salt
  • magnesium salt calcium Alkaline earth metal salts such as salts
  • ammonium salts such as dimethylamine salts and triethylamine salts
  • inorganic salts such as hydrochlorides, perchlorates, sulfates, and nitrates
  • acetates, methanesulfonates Organic acid salts and the like.
  • the haloalkene compound represented by the formula (I) may have a geometric isomer or an optical isomer, and the present invention includes both isomers and isomer mixtures.
  • the haloalkene-based compound represented by the formula (I) or a salt thereof (hereinafter, abbreviated as the compound of the present invention) can be produced according to the following reactions [A] to [C] and a usual salt production method. . H 2 NQ
  • Reaction [A] is performed in the presence of a base, if necessary.
  • the base include, for example, trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6-dimethylpyridine, 4-pyrrolidinopyridine, N-methylmorpholine, N, N —Dimethylaniline, N, N—Jetylaniline, N—Ethyl—N—Methylaniline, 1,8—Diazabicyclo [5.4.0] 17-Pendecene, 1,4-Diazabicyclo [2.2.2]
  • Octane Tertiary amines such as sodium and potassium; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium butoxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; Alkali metal hydroxides such as sodium hydroxide and potassium hydroxide An alkali metal
  • Reaction [A] is performed in the presence of a solvent, if necessary.
  • the solvent may be any solvent which is inert to the reaction, for example, aliphatic hydrocarbons such as pentane, hexane, heptane, octane, cyclohexane; benzene, toluene, xylene, pyridine and the like.
  • Aromatic hydrocarbons such as benzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, and trichlorobenzene; getyl ether, butyl ethyl ether , Such as tetrahydrofuran, dioxane, dimethoxyethane, and anisol Esters such as methyl acetate, ethyl acetate, and propyl acetate; ketones such as acetone, getyl ketone, methyl ethyl ketone, and methyl isobutyl ketone; acetonitrile, propionitrile, N, N-dimethylformamide, One or more kinds are appropriately selected from polar aprotic solvents such as tyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide, and N-methylpyrrolidon
  • Reaction [A] is performed in an atmosphere of an inert gas as necessary.
  • the inert gas include gases such as nitrogen, helium, and argon.
  • the reaction temperature of the reaction [A] is usually -78 to +250: desirably 0 to 150, and the reaction time is usually 0.1 to 72 hours, desirably 0.1 to 24 hours.
  • the reaction [B] is carried out by azeotropic dehydration in the presence of a solvent or in the presence of a condensing agent.
  • the solvent used in the azeotropic dehydration may be any solvent as long as it is an inert solvent for the reaction.
  • one or more of the solvents exemplified in the above-mentioned reaction [A] are appropriately selected.
  • a solvent may be used as necessary.
  • the solvent used here may be any solvent that is inert to the reaction.
  • One or more kinds are appropriately selected from those exemplified in the reaction [A].
  • Examples of the condensing agent used in the reaction [B] include 1,3-dicyclohexylcarbodiimide, 1,3-diisopropylcarbodiimide, and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride.
  • Carbodiimides dichloridophenyl phosphate, getyl phosphorocyanidate, 1 , 3,5-Triaza 2,4,6 —Triphosphorine 1,2,2,4,4,6,6-hexahexyl chloride, cyanuric chloride, isobutyl chloroformate, chlorosulfonyl isocyanate, N, N ' —Capillonyldiimidazole, trifluoroacetic anhydride and the like.
  • the condensing agent is used in an amount of 1 to 5 times, preferably 1 to 2 times the mole of the compound of the formula (IV).
  • Reaction [ ⁇ ] is performed in the presence of a base, if necessary.
  • the base include, for example, trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6-dimethylpyridine, 4-pyrrolidinopyridine, ⁇ ⁇ ⁇ -methylmorpholine, ⁇ , ⁇ —
  • tertiary amines such as dimethyl aniline, ⁇ , ⁇ -getyl aniline and ⁇ -ethyl- ⁇ -methyl aniline are appropriately selected.
  • the base is used in an amount of 0.1 to 5 times, preferably 0.1 to 2 times the mole of the compound of the formula (IV).
  • Reaction [ ⁇ ] is performed under an inert gas atmosphere as necessary.
  • the inert gas include gases such as nitrogen, helium, and argon.
  • the reaction temperature of the reaction [ ⁇ ] is usually -78 to +250, preferably 0 to 150, and the reaction time is usually 0.1 to 72 hours, preferably 0.1 to 24 hours.
  • Reaction [C] is performed in the presence of a base, if necessary.
  • a base is appropriately selected from those exemplified in the above reaction [A].
  • the base is used in an amount of 0.0 :! to 5 times, preferably 0.01 to 2 times, the mole of the compound of the formula (V).
  • Reaction [C] is performed in the presence of a solvent, if necessary.
  • Solvents are solvents inert to the reaction Any one of them may be used as long as it is selected, for example, one or two or more from those exemplified in the reaction [A].
  • Reaction [C] is performed under an inert gas atmosphere as necessary.
  • the inert gas include gases such as nitrogen, helium, and argon.
  • the reaction temperature of the reaction [C] is usually -78 to +250 t: desirably 0 to 150, and the reaction time is usually 0.1 to 72 hours, desirably 0.1 to 24 hours.
  • Each starting material represented by the formula (II), the formula (IV) or the formula (V) used in the above-mentioned reactions [A] to [C] is a known compound or WO92Z15555 It can be produced by the method described in No. 5, EP 4 332 861, or a method analogous thereto. More specifically, (1) a method described on pages 15 to 16 of W092Z155555, followed by a method of appropriately performing ordinary chlorination or esterification, Synthetic Examples 16 to 22, 28 or 42, and methods analogous thereto, and (2) Synthetic Examples 8 to 10 or 1 in EP 4 328 61 It can be produced by the method described in 6, and a method analogous thereto.
  • the pest controlling agent containing the compound of the present invention is, for example, a controlling agent for various pests which are problematic in the field of agriculture and horticulture, that is, a controlling agent for agriculture and horticulture, and a controlling agent for pests parasitic on animals, that is, animals. Particularly useful as a parasitic control agent.
  • agricultural and horticultural pest control agents are useful as insecticides, miticides, nematicides, soil-killing insecticides, and, for example, Namihadani, Nisenamihadani, Kansahada two, Citrus spider mite, Apple spider mite, Tyrannophorida, Plant-parasitic mites such as Citrus abandonii, Scarlet mite, etc .; Aphids such as Peach aphid, Aphid aphid, Acer aegypti, Coleoptera, Spodoptera litura, Codling moth, Ball worm, Tobacco bad worm, Gypsophila, Kobnomimeiga, Chiyanococcus Tribulus terrestris, Colorado potato beetle, Periplane beetle, Ball wisdom building, Scarabaeidae, Leafhoppers, Scarabaeidae, Stinkbugs, Whiteflies, Azamazuma, Babayu, Hanabae, Scaraba
  • the agricultural and horticultural pesticide containing the compound of the present invention is particularly effective for controlling plant parasitic mites, agricultural pests, plant parasitic nematodes, and the like.
  • the agricultural and horticultural pesticidal composition containing the compound of the present invention is also effective for controlling various pests that are resistant to chemicals such as organophosphates, carbamates, and synthetic pyrethroids.
  • the compound of the present invention has excellent systemic transfer properties
  • soil harmful insects, mites and nematodes are treated.
  • it can also control pests in foliage.
  • Another desirable embodiment of the pesticidal agent containing the compound of the present invention is to comprehensively control the above-mentioned plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods, soil pests and the like. Pest control agents for agricultural and horticultural use.
  • Agricultural and horticultural pesticides containing the compound of the present invention are usually mixed with the compound and various agricultural auxiliaries to obtain powders, granules, wettable granules, wettable powders, aqueous suspensions, oils It is used in various forms such as suspensions, aqueous solvents, emulsions, liquids, pastes, aerosols, and micro-sprays, but is used in the usual fields as long as it meets the purpose of the present invention. It can be in any of the known formulation forms.
  • Adjuvants used in the formulation include diatomaceous earth, slaked lime, calcium carbonate, talc, white rib, a mixture of violin, bentonite, kaolinite and sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch.
  • Solid carriers such as water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, dimethylformamide, dimethylacetamide, N-methyl-2 —Pyrrolidone, Arco Solvents such as fatty acid salts, benzoates, alkyl sulfosuccinates, dialkyl sulfosuccinates, polycarboxylates, alkyl sulfates, alkyl sulfates, alkyl aryl sulfates, alkyl diglycolates Tersulfate, alcohol sulfate, alkyl sulfonate, alkyl aryl sulfonate, aryl sulfonate, lignin sulfonate, alkyl diphenyl ether disulfonate
  • these components can be appropriately selected and used without departing from the purpose of the present invention.
  • adjuvants they can be appropriately selected from those known in the art and used, for example, extenders, thickeners, anti-settling agents, anti-freezing agents, dispersion stabilizers, and safeners.
  • auxiliaries such as fungicides can also be used.
  • the compounding ratio of the compound of the present invention and various adjuvants is 0.001: 99.999 to 95: 5. Preferably, it is 0.005: 99.995 to 90:10.
  • the concentration of the active ingredient is 0.05 to 800,000 ppm, preferably 0.5 to 500,000 ppm, and the application rate per unit area is 0.05 to 500,000 g of the compound of the present invention per hectare, preferably 1 to 500 g. It is 30000g.
  • the present invention also includes a method for controlling pests by such an application method, particularly a method for controlling plant parasitic mites, agricultural pests, and plant parasitic nematodes.
  • Various formulations of the agricultural and horticultural pesticides containing the compound of the present invention, or the diluted product thereof, are applied by a generally applied application method, that is, spraying (for example, spraying, spraying, misting, atomizing, Spraying, water surface application, etc.), soil application (mixing, irrigation, etc.), surface application (application, dressing, coating, etc.), immersion poison bait etc.
  • spraying for example, spraying, spraying, misting, atomizing, Spraying, water surface application, etc.
  • soil application mixtureing, irrigation, etc.
  • surface application application, dressing, coating, etc.
  • immersion poison bait etc etc.
  • It can also be applied by the so-called ultra low volume spraying method. In this method, it is possible to contain 100% of the active ingredient.
  • the agricultural and horticultural pesticide containing the compound of the present invention can be mixed with or used in combination with other agricultural chemicals, fertilizers, chemical mitigation agents, and the like. In this case, more excellent effects and operability are exhibited.
  • Other pesticides include herbicides, insecticides, acaricides, nematicides, soil pesticides, fungicides, antivirals, attractants, antibiotics, plant hormones, plant growth regulators, etc.
  • a mixed pest control composition in which the compound of the present invention and one or more active compounds of other pesticides are mixed or used in combination is preferable in terms of application range, timing of chemical treatment, control activity and the like. It is possible to improve in the direction.
  • the compound of the present invention and the active ingredient compound of another pesticide may be prepared separately and mixed at the time of spraying, or both may be prepared together and used. The present invention Such mixed pest control compositions are also included.
  • the mixing ratio between the compound of the present invention and the active ingredient compound of another pesticide cannot be unconditionally defined due to differences in weather conditions, formulation, application time, place of application, types of pests and occurrences, but generally 1: 300 to 300: 1, preferably 1: 100 to 100: 1.
  • the appropriate application amount is 0.1 to 50,000 g, preferably 1 to 30,000 g, as the total amount of the active ingredient compound per hectare.
  • the present invention also includes a method for controlling pests by a method for applying such a mixed pest control composition.
  • Examples of the active ingredient compounds (generic names; including some applications) of pesticides, acaricides, nematicides or soil pesticides, that is, pesticides in the above-mentioned other pesticides include, for example, profenophos (Proienoios), Dichlorvos, Fenamiphos, Feni trotliion, EPN, Diazinon, Diaz inon, Chlorpyri fos-methyl, Acephate, Prothiophos (Fos thiazate), Phosphocarb (Phosphoc arb), Cadusaios, Disulfoton (Dis l foton), Chlorpyrifos (Chi orpyri fos), Demeton-S-methyl (Deme ton-S-methyl), Dimethoate (Dimethoat e), Organophosphate compounds such as methamidophos; Carbaryl, Propoxur, Aldi Carp (Aldicarb), Carpo
  • Nereistoxin derivatives such as Cartap, Thiocyclam, Bensul tap;
  • Organochlorinated compounds such as dicofol and tetradifon; organometallic compounds such as fenbutat in oxide; fenvalerate, permethrin, and cypermethrin ), Deltamethrin (Del tamethrin), cyhalothrin (Cyhalothrin), tefluthrin (Tei luthrin), etofenprox (Ethoienprox)., Biphen Pyrethroid compounds such as Surin (Bifenthrin);
  • Juvenile hormone-like compounds such as methoprene, pyriproxyien, and phenoxycarb;
  • Pyridazinone compounds such as pyridaben
  • Pyrazole-based compounds such as fenpyroximate, fipronil, tebufenpyrad, ethiprole, tolifenpyrad, and acetoprole;
  • Neonicotinoids such as imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiacloprid, thiamethoxam, clothianidin, dinotefuran, etc .;
  • Hydrazine compounds such as Tebuienozide, Methoxyienozide and Chroma fenozide;
  • microbial pesticides such as BT agents, entomopathogenic virus agents, entomopathogenic fungal agents, nematode pathogenic fungal agents, avermectin (Avennect in), emamectin benzoate (Emamect in-Benzoate), mill It can be mixed or used in combination with antibiotics such as bemectin (Mil bemect in), spinosad (Sp inosad), and ivermectin (Ivermect in).
  • antibiotics such as bemectin (Mil bemect in), spinosad (Sp inosad), and ivermectin (Ivermect in).
  • Examples of the active ingredient compound of the fungicide in the above-mentioned other pesticides include: Pyrimidinamine compounds such as);
  • Quinoxaline compounds such as Quinomethionate; dithiocarbamate compounds such as Maneb, Zineb, Mancozeb, Polycarbamate, and Propineb; fthalide ), Organochlorine compounds such as Chlorothaloni, Quintt ozene;
  • Imidazole compounds such as benomyl, thiophanate-methyl, carbendazim, cyazofamid;
  • Cyanoacetamide compounds such as Cymoxanil
  • Metalaxyl, Oxadixyl, Offurace Phenylamide compounds such as Benalaxyl, Furalaxyl, Cyprofuram;
  • Sulfenic acid compounds such as dichlofluanid
  • copper compounds such as cupric hydroxide and organic copper (Oxine Copper) isoxazoles such as hydroxyisoxazole Compound
  • N-halogenothioalkyl compounds such as Captan, Captaiol, and Folpet;
  • Dicarpoxyimide compounds such as Procymidone, Iprodione, Vin clozol in;
  • Benzanilide compounds such as Flutolanil, Mepronil, Zoxamide;
  • Piperazine-based compounds such as triforine (Tri for ine);
  • Pyridine-based compounds such as Pyri enox
  • Carpinol-based compounds such as Fenarimol and Flutriaiol
  • Piperidine compounds such as Fenpropidine
  • Morpholine compounds such as fenpropimorph
  • organotin compounds such as fentin hydroxide and fentin acetate
  • Urea-based compounds such as Pencycuron
  • Cinamic acid-based compounds such as Dimethomorph
  • Phenylcarbamate-based compounds such as Diethoencarb Cyanopyrrole-based compounds such as Fludioxonil and Fenpiclonil;
  • Strobilurin-based compounds such as Metominoien, Trifloxystrobin, and Picoxystrobin; Oxazolidinone-based compounds such as Famoxadone;
  • Thiazolecarboxamide-based compounds such as Ethaboxam
  • silylamide-based compounds such as silthiopham
  • Amino acid amide carbamate compounds such as Iproval icarb
  • Imidazolidine-based compounds such as phenamidone (Fenami done);
  • Hydroxyanilide compounds such as fenhexamid; benzenesulfonamide compounds such as Flusul iamide; stoline viruline compounds such as pyraclostrobin; atraquinone compounds; crotone Acidic compounds; antibiotics and other compounds such as isoprothiolane, tricyclazole, pyrochlorone, pyrolouilon, diclomezine, probenazole, quinoxyphen, quinoxyphen, and propamocap hydrochloride Salt (Propamocarb Hydrochloride), Spiroxamine, Chloropicrin, Dazomet, Metan-sodium salt; etc. Others, which can be mixed with or used in combination with the compound of the present invention as, Eg to enable ingredient compounds in the herbicides as disclosed in Farm Chemicals Handbook (1998 year edition), particularly those of soil treatment type.
  • Animal parasite control agents include, for example, ectoparasites that infest the body surface of the host animal (back, axillary, lower abdomen, inner thigh, etc.), and the host animal body (stomach, intestinal tract, lung, heart, liver) , Blood vessels, subcutaneous, lymphatic tissue, etc.) However, it is especially effective in controlling ectoparasites.
  • Ectoparasites include, for example, animal parasitic mites and fleas. These types are so numerous that it is difficult to list them all.
  • Animal parasitic mites include, for example, the red tick (Bonphilns microolns), the red tick (Rhipicephalns sanguineus), the red tick (Hafil aphvsal is longi ornis), the red tick (Haemaphvsal is flava), , Chinese ticks (Hae sect. Hvsal is cone inn 2), Chinese ticks (HaemaDhvsal is i ponica), Haemaph vs. is kitankai, Japanese ticks (Hae recitation hvsal is is), Yamato matani (1 ⁇ us ode) ), Evening Nematodes (Txodes nipponen.
  • Nantotsugamushi (Kntrnmh inula wichmanni), Akatatsugamushi (LeDtotro mhidiiim akamushi), Futteggamushi (LeDtotromhidium pallidum), Fujitsugamushi (RDtntromhidinm fn3 ⁇ 4i), Tosattini t ⁇ ntni sntntr ⁇ n, sattini t ⁇ ntni s ⁇ ntni sntn tibini s Species such as Egg trumpet beetle (Eu trnmhi ula al frpddiigesi) and Miyagawa evening worm (Helen imil a mivaeawai); 13 ⁇ 4 blakei); ⁇ ⁇ (PsoroptRS nnimili), ⁇ ⁇ (Chorinptes hovis), ⁇ ⁇ (Oto
  • Pesticides are particularly effective in controlling ticks and the like.
  • the fleas include, for example, ectoparasitic wingless insects belonging to the order Flea (SiDhnnaptftra), and more specifically, fleas belonging to the flea family (Pnlicidafi), the flea family (CfiratRDhvlliis), and the like.
  • the fleas belonging to the family Fleas include flea (CtenocfiDhal ides can is), cat flea (ClenncRDhal iries fel is), flea flea (Pnlex irritans), nipple flea (Kchid ophaga gal 1 ina ea), and capps enznops nips vna ), Mekranez's flea (fiDtopsvl la een is), European flea (NosoDsvllus fasciatns), Yamato flea ( ⁇ ⁇ np.svllns anisns) and the like.
  • the animal parasite control agent containing the compound of the present invention is effective for controlling fleas belonging to the family Flea, especially fleas and cat fleas.
  • ectoparasites include, for example, lice such as ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ , ⁇ ⁇ ⁇ ; ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Pests and the like.
  • examples of the endoparasites include nematodes such as lungworm, benthic, nodular worm, stomach parasite, roundworm, and filamentous worm; tapeworm; fluke; coccididium, malaria parasite, gut sporeworm, Protozoa such as Toxoplasma and Cryptosporidium can be mentioned.
  • Host animals include pets such as dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, egrets, ferrets, and birds (eg, wild birds, birds, birds, mysterious birds, sparrows, parakeets, giant pine trees, canaries); Livestock such as turtles, horses, bushes, and higgies; poultry such as ducks and chickens.
  • the animal parasite control agent containing the compound of the present invention is effective for controlling pests parasitic on pets or livestock, especially ectoparasites. It is particularly effective on dogs and cats in pets, and particularly effective on pests and pests in livestock.
  • the compound of the present invention When used as an animal parasite control agent, it may be used as it is, and powders, granules, tablets, powders, capsules, liquids, emulsions, and aqueous suspensions together with appropriate adjuvants Can be formulated and used in various forms such as oily suspensions You.
  • any preparation form usually used in this field can be used as long as the object of the present invention is satisfied.
  • the adjuvant used in the preparation examples include anionic surfactants and nonionic surfactants exemplified as the adjuvants for the agricultural and horticultural pesticides; cetyltrimethylammonium bromide; Cationic surfactants: water, acetone, acetonitrile, monomethylacetamide, dimethylacetamide, dimethylformamide, 2-pyrrolidone, N-methyl-2-pyrrolidone, kerosene, triacetin, methanol, ethanol, isopropanol, benzyl Alcohol, ethylene glycol, propylene glycol, polyethylene glycol, liquid polyoxyethylene glycol, butyl diglycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethylene Solvents such as butyl ether, dethylene glycol normal butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol normal butyl ether; butylhydroxyanisole,
  • Vegetable oils and mineral oils carriers such as lactose, sucrose, glucose, starch, wheat flour, corn flour, soybean oil cake, defatted rice bran, calcium carbonate, and other commercially available feed ingredients.
  • auxiliary components can be appropriately selected and used as long as they do not deviate from the object of the present invention.
  • auxiliary agents they can be appropriately selected and used from those known in the art.
  • auxiliary agents appropriately selected from the above-mentioned various auxiliary agents used in the agricultural and horticultural fields, etc. Can also be used.
  • the compounding ratio of the compound of the present invention and various adjuvants is usually about 0.1: 99.9 to 90:10. In actual use of these preparations, they can be used as they are or diluted to a predetermined concentration with a diluent such as water, and various spreading agents (surfactant, vegetable oil, mineral oil, etc.) can be added as necessary. Can be used.
  • a diluent such as water
  • various spreading agents surfactant, vegetable oil, mineral oil, etc.
  • the administration of the compound of the present invention to a host animal is performed orally or parenterally. Examples of the oral administration method include a method of administering a tablet, a liquid preparation, a capsule, a pharmacy, a biscuit, minced meat, and other feeds containing the compound of the present invention.
  • parenteral administration for example, a method of preparing the compound of the present invention into an appropriate formulation and then injecting it into the body by intravenous administration, intramuscular administration, intradermal administration, subcutaneous administration, etc .; ) Treatment, pour-on treatment, spray treatment, etc .; and a method in which a resin piece containing the compound of the present invention is implanted under the skin of a host animal.
  • the dose of the compound of the present invention to the host animal varies depending on the administration method, administration purpose, disease symptoms, etc., but is usually 0.01 mg to 100 g per 1 kg body weight of the host animal. Preferably, it is administered in a ratio of 0.1 mg to 10 g.
  • the present invention also includes a method for controlling pests by the above-mentioned administration method or dose, particularly a method for controlling ectoparasites or endoparasites.
  • the compound of the present invention When the compound of the present invention is used as an animal parasite control agent, various vitamins, minerals, amino acids, nutrients, enzyme preparations, antipyretics, sedatives, anti-inflammatory agents, bactericides, coloring agents, and fragrances together with auxiliary agents It can be mixed with or used in combination with a preservative. Also, if necessary, mix or use in combination with other animal drugs and pesticides, such as anthelmintics, anticoccidial agents, insecticides, acaricides, flea killers, nematicides, fungicides, antibacterial agents, etc. In this case, even better effects may be exhibited.
  • the present invention includes a mixed pest control composition in which various components as described above are mixed or used in combination, and a method for controlling pests using the same, particularly a method for controlling ectoparasites or endoparasites. included.
  • Desirable embodiments of the compound of the present invention are as follows. However, the present invention is not limited to these.
  • Q is 1) Chenyl, furyl, pyrrolyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, thiadiazolyl, triazolyl, dithiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzothiazolyl, benzothiazolyl, benzothiazolyl, benzothiazolyl, benzothiazolyl, benzothiazolyl, benzothiazolyl Lil, Benzot A heterocyclic group selected from the group consisting of riazolyl, quinolyl, isoquinolyl and quinazolinyl; 2) a partially saturated heterocyclic group in which a part of these heterocyclic groups is hydrogenated; 3) these heterocyclic groups are completely hydrogenated An added saturated heterocyclic group, or 4) an oxo or thioheterocyclic group in which the
  • heterocyclic group is chenyl, furyl, pyrrolyl, thiazolyl, oxazolyl
  • Q is chenyl, furyl, pyrrolyl, thiazolyl, isothiazolyl, oxosazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiadiazolyl, triazolyl, dithiazolyl, pyridyl, pyridazinyl, pyrimidinyl, virazinyl, triazinyl, triazinyl, triazinyl, triazinyl, triazinyl, triazinyl, triazinyl, triazinyl, triazinyl, triazinyl , Benzofuranyl, indolyl, isoindolyl, benzothiazolyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, benzimidazolyl, indazolyl, benzothiadiazolyl, benzotriazolyl, quinolyl, is
  • Q is chenyl, furyl, pyrrolyl, thiazolyl, isothiazolyl, oxosazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiadiazolyl, triazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzofurinyl, benzofurnyl, benzofurinyl, benzofurinyl, benzofurinyl , Benzoisothiazolyl, Benzoxazolyl, Benzoisoxazolyl, Benzimidazolyl, Indazolyl, Benzothiadiazolyl, Benzotriazolyl, Quinolyl, Isoquinolyl, Phthalazinyl, Quinazolinyl, Quinoxalinyl, Benzotriazinyl, 4, 5-dihydrothiazolyl,
  • Q is chenyl, furyl, pyrrolyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, thiadiazolyl, triazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzothiazolyl, benzoimidazolyl, benzothiazolylol, benzothiazolylol, benzothiazolylol, benzothiazolylol , Quinolyl, isoquinolyl, quinazolinyl, 4,5-dihydrothiazolyl, 4,5-dihydro-1H-birazolyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, 2-oxotetrahydrofuranyl, 2-oxopyrrolidinyl 1,2-dioxothiazolidinyl, 5-ox
  • Q is chenyl, furyl, pyrrolyl, thiazolyl, oxazolyl, isoxazolyl, pyrazolyl, thiadiazolyl, triazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzothiazolyl, benzoimidazolyl, benzothiazolyzol Quinolyl, isoquinolyl, quinazolinyl, 4,5-dihydrothiazolyl, 2-oxopyrrolidinyl, 3-oxo-1,2,3-dihydro-1H-pyrazolyl and 2,6-dioxol 1,2,3
  • the substituent of the heterocyclic moiety is, Nono androgenic, nitro, Shiano, _ 8) Aruki Le, halo (Ci - 8) alkyl, (C 3 _ 8) cycloalkyl, Ariru, - NR 1 R 2, - oR 1, - SR 1 -COR 1 , -C0 2 R 1 and - CH 2 CN (wherein R 1 a hydrogen atom or each independently are ( ⁇ _ 8) alkyl as) at least one of Bareru selected from the group consisting of The haloalkene compound of the formula (I) or a salt thereof
  • Q is chenyl, furyl, pyrrolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiadiazolyl, triazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzofurinyl, benzofurinyl, benzofuranyl, benzofurinyl, benzofurinyl, benzofurnyl, benzofurinyl Hetero selected from the group consisting of thiazolyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl, indazolyl, benzothiadiazolyl, benzotriazolyl, quinolyl, isoquinolyl, phthalazinyl, quinazolinyl, quinoxalinyl and benzotriazinyl A
  • Test Example 1 Effect test on the sweet potato nematode
  • a drug solution prepared so that the concentration of the compound of the present invention was 200 ppm was prepared.
  • the leaves were transplanted into cups (8 cm in diameter and 7 cm in height), leaving only one of the primary leaves of the rice, and 20 adult Nami-Nada two were released. This was immersed in the above-mentioned chemical solution together with the kidney leaves, and was air-dried and left in a constant temperature room with illumination at 25. On the second or third day after the treatment, viability was determined, and the adult kill ratio was determined by the following formula. Compound Nos.
  • Rice seedlings were immersed in a chemical solution prepared so that the concentration of the compound of the present invention became 200 ppm, air-dried, and the roots were wrapped with moist absorbent cotton and placed in test tubes. Ten larvae of Himetobin power were released into this, and the tube mouth was covered with gauze and left in a constant temperature room with lighting at 25. Release On the 5th day after the insects, viability was determined, and the mortality was determined by the following formula. Compound Nos.
  • Mortality (%) (Number of dead insects Z Number of released insects) X 100 Test example 4 Peach aphid insecticidal test
  • a drug solution prepared so that the concentration of the compound of the present invention was 200 ppm was prepared.
  • a pot with only one true leaf left (8 cm in diameter, 7 cm in height) After applying adhesive to the petiole of the planted eggplant, inoculate two or three adult female peach moth aphids on the true leaf. We let them pup. On the second day after inoculation, the adults were removed and the number of larvae was counted.
  • the eggplant leaves infested with the larvae were immersed in the above-mentioned chemical solution, air-dried, and allowed to stand in a constant temperature room with illumination at 25. On the 5th day after the treatment, viability was determined, and the mortality was determined by the following formula.
  • the detached insects were regarded as dead insects. Compound Nos.
  • Mortality (%) (Number of dead insects Number of larvae after treatment) X 100 Test Example 5 Drug efficacy test against Haemaphysalis longicornis
  • the survival rate was determined from the number of rollover mites at each observation, and the corrected mortality was calculated using the correction formula of the following apot. Then, a probit-time line was drawn to determine the half-lethal time (KT 5 personallyvalue) For compound No. 186, the corrected mortality after 2 hours was 100%. However, both the first and second sessions lasted 68 minutes.
  • Xylene 50 parts by weight or more components are uniformly mixed and dissolved to form an emulsion.
  • Fine silica powder A mixture of 25 parts by weight or more of the component and the compound of the present invention are mixed in a weight ratio of 4: 1 to obtain a wettable powder.
  • (1) to (3) are uniformly mixed in advance, diluted with an appropriate amount of acetone, and sprayed on (4) to remove the acetone to obtain granules.

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  • Organic Chemistry (AREA)
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  • Tropical Medicine & Parasitology (AREA)
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  • Wood Science & Technology (AREA)
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  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
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  • Hydrogenated Pyridines (AREA)
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Abstract

Cette invention a trait à des haloalcènes correspondant à la formule générale (I), se révélant des plus utiles comme agents phytosanitaires. Dans cette formule, X1 et X2 représentent, chacun, un halogéno, Y représente un hydrogène ou un halogéno, la valeur de n est comprise entre 0 et 5 et Q représente, (1), un groupe hétérocyclique choisi dans le groupe formé par du thiényle, du furyle, du pyrrolyle, du thiazolyle, de l'isiothiazolyle, de l'oxazolyle, de l'isoxazolyle etc., (2), un groupe hétérocyclique partiellement saturé dérivé de ce groupe hétérocyclique ayant subi une hydrogénation partielle, (3), un groupe hétérocyclique saturé dérivé de ce groupe hétérocyclique ayant subi une hydrogénation complète ou, (4), un groupe oxo- ou thioxo-hétérocyclique dérivé de dithiazolyle, d'oxazinyle, de thiazinyle, d'un groupe hétérocyclique partiellement saturé ou d'un groupe hétérocyclique saturé par la conversion en oxo ou thioxo au niveau d'une fraction méthylène (à condition que chaque fraction hétérocyclique puisse être substituée).
PCT/JP2003/004331 2002-04-05 2003-04-04 Haloalcenes, procede de production et agents de protection phytosanitaire les contenant WO2003084927A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104163792A (zh) * 2013-05-20 2014-11-26 湖南化工研究院 N-吡啶酰胺类化合物及其制备方法与应用

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04154740A (ja) * 1989-12-15 1992-05-27 Schering Ag ハロゲン化オレフィン、これを含有する殺虫剤および殺ダニ剤ならびに虫およびダニを駆除する方法

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04154740A (ja) * 1989-12-15 1992-05-27 Schering Ag ハロゲン化オレフィン、これを含有する殺虫剤および殺ダニ剤ならびに虫およびダニを駆除する方法

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104163792A (zh) * 2013-05-20 2014-11-26 湖南化工研究院 N-吡啶酰胺类化合物及其制备方法与应用
WO2014187298A1 (fr) * 2013-05-20 2014-11-27 湖南化工研究院有限公司 Composé n-pyridine-amide et procédé de préparation et utilisation de ce composé

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