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WO2001000568A1 - Derives hydrazones et pesticides - Google Patents

Derives hydrazones et pesticides Download PDF

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Publication number
WO2001000568A1
WO2001000568A1 PCT/JP2000/004232 JP0004232W WO0100568A1 WO 2001000568 A1 WO2001000568 A1 WO 2001000568A1 JP 0004232 W JP0004232 W JP 0004232W WO 0100568 A1 WO0100568 A1 WO 0100568A1
Authority
WO
WIPO (PCT)
Prior art keywords
halogen atom
phenyl
alkyl
substituted
optionally substituted
Prior art date
Application number
PCT/JP2000/004232
Other languages
English (en)
Japanese (ja)
Inventor
Kazumi Yamamoto
Kazuhiko Oyama
Takeshi Teraoka
Original Assignee
Meiji Seika Kaisha, Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Meiji Seika Kaisha, Ltd. filed Critical Meiji Seika Kaisha, Ltd.
Priority to AU57040/00A priority Critical patent/AU5704000A/en
Priority to JP2001506981A priority patent/JP4712261B2/ja
Publication of WO2001000568A1 publication Critical patent/WO2001000568A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/63—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C255/65—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to nitrogen atoms
    • C07C255/66—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to nitrogen atoms having cyano groups and nitrogen atoms being part of hydrazine or hydrazone groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
    • C07C323/48—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Definitions

  • the present invention relates to a novel hydrazone derivative and a pesticidal agent containing the same as an active ingredient.
  • Japanese Patent Application Laid-Open No. 9-143032 discloses a compound having a cycloalkyl group, and includes agricultural pests, sanitary pests, grain storage pests, clothing pests, house pests, and various plant pathogens. It shows that it shows an effective control effect on pests. However, no report has been made on a hydrazone derivative having a substituted cyclopropyl group and its pesticidal activity.
  • An object of the present invention is to provide a compound having excellent pest control activity and a pest control agent.
  • the compounds according to the invention are compounds of the formula (I) and salts and solvates thereof.
  • R 'RR 3, R and R 5 which may be the same or different
  • Ci-4 alkyl optionally substituted by a halogen atom; or a phenyl optionally substituted by d-4 alkyl or d-4 alkoxy (the alkyl and the alkyl moiety may be substituted by a halogen atom),
  • R 1 RR 3 , R and: 5 do not all represent a hydrogen atom
  • R 6 is
  • heterocyclic group is a halogen atom; an alkyl optionally substituted by a halogen atom; a d- 4 alkoxy optionally substituted by a halogen atom
  • R 1 1 and R 1 2 may be the same or different dates, d-4-alkyl or d - 4 alkoxy (said alkyl And the alkyl moiety may be substituted by a halogen atom).
  • the compounds according to the invention are useful as pesticides.
  • alkyl or “alkoxy” as a group or part of a group means an alkyl or alkoxy group, wherein the group is straight, branched, or cyclic.
  • d-4 alkoxy refers to linear alkoxy such as methoxy, ethoxy, n-propoxy, n-butoxy, branched alkoxy such as isopropyloxy, isobutyloxy, tert-butyloxy, and cycloproviroxy.
  • the halogen atom means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • the saturated or unsaturated 5- or 6-membered heterocyclic ring means a heterocyclic ring containing at least one heteroatom selected from a nitrogen atom, an oxygen atom, and a sulfur atom.
  • this complex ring include a pyridine ring, a furan ring and a thiophene ring.
  • alkyl optionally substituted with means that one or more hydrogen atoms on the alkyl are substituted with one or more substituents (which may be the same or different). Mean good alkyl. It will be apparent to those skilled in the art that the maximum number of substituents can be determined depending on the number of substitutable hydrogen atoms on the alkyl. The same applies to groups having a substituent other than alkyl, for example, alkoxy, phenyl, and heterocyclic groups.
  • R 1 and R 2 may be the same or different and preferably represent a C 4 alkyl which may be substituted by a hydrogen atom or a halogen atom.
  • R 3 and R 4 may be the same or different and preferably represent a halogen atom.
  • R 5 preferably represents a hydrogen atom; an optionally substituted d-4 alkyl; or an optionally substituted phenyl.
  • the phenyl represented by R 6 is preferably 1-, 2- or 3-substituted by one or more substituents which may be the same or different.
  • substituents which may be the same or different.
  • “1, 2-, or 3-substituted” means substitution with one, two, or three substituents.
  • R 6 is preferably phenyl (which phenyl may optionally halogen atom (same or different dates); Shiano; nitro; halogen atoms which may be substituted by C, - 4 alkyl; optionally substituted by a halogen atom Which is substituted by d-4 alkoxy, and is preferably substituted by 1, 2-, or 3-).
  • R 7 preferably represents a hydrogen atom or C ⁇ 4 alkyl substituted by C 4 alkylthio or C 4 alkoxy.
  • Preferred compounds of the formula (I) include:
  • R 1 and R 2 may be the same or different and each represents a Ci- 4 alkyl which may be substituted by a hydrogen atom or a halogen atom,
  • R 3 and R 4 may be the same or different and represent a halogen atom
  • R 5 represents a hydrogen atom; d- 4 alkyl which may be substituted; or phenyl which may be substituted;
  • R 6 represents an optionally substituted phenyl and / or an optionally substituted 5 or 6 membered saturated or unsaturated heterocyclic group
  • More preferred compounds of the formula (I) include:
  • R 1 and R 2 represent a hydrogen atom
  • R 3 and R 4 represent a halogen atom, for example, a chlorine atom,
  • R 5 represents unsubstituted d 4 alkyl
  • R 6 represents phenyl, which is a halogen atom (which may be the same or different); cyano; nitro; d-4 alkyl optionally substituted by a halogen atom; or substituted by a halogen atom.
  • R 7 represents d- 4 alkyl substituted by a hydrogen atom or C 4 alkoxy.
  • the compounds of formula (I) can form salts.
  • the salt of the compound of the formula (I) include alkali metal salts such as lithium salt, sodium salt and potassium salt; alkaline earth metal salts such as magnesium salt and calcium salt; ammonium salt, methyl ammonium salt and dimethyl ammonium salt.
  • Ammonium salts such as trimethylammonium salt, dicyclohexyl ammonium salt; triethylamine, trimethylamine, diethylamine, pyridine, ethanolamine, triethanolamine, dicyclohexylamine, proforcein, benzylamine, N Organic amine salts such as —methylbiperidine, N-methylmorpholine, and getylaniline; and basic amino salts such as lysine, arginine, and histidine.
  • the compounds of formula (I) can form solvates, for example hydrates or ethanolates.
  • Isomers such as geometric isomers, may exist in the compounds of formula (I), but any such isomers and mixtures thereof are also encompassed by the present invention.
  • the compound of the formula (I) can be produced according to the method described in JP-A-9-144032.
  • HI in an appropriate reaction solvent (for example, water or a mixed solvent of water and an organic solvent) whose pH has been adjusted to 4 to 8 with sodium acetate, sodium carbonate, etc., from —20 ° C. It can be produced by reacting at room temperature.
  • an appropriate reaction solvent for example, water or a mixed solvent of water and an organic solvent
  • the compound of the formula (I) in which R 7 is substituted by a substituent is obtained by the compound obtained by the above step.
  • the substituted cyclopropane carboxylic acid derivative of formula (II) can be prepared by the method described in Synthesis, (1977), 472 and Synthesis, (1983), 308, wherein the ester of substituted cyclopropane carboxylic acid of formula (IV) (W - 0- C - 4 represents an ester residue such as alkyl) or salt product (W represents a halogen atom such as chlorine)!:
  • the compound of the formula (IV) is disclosed in JP-B-55-42444, JP-A-62-210855, JP-A-63-54350. It can be manufactured according to the method described.
  • the compound of the formula (IV) is substituted with a compound of the formula (V) which is commercially available or can be obtained by a known synthesis method.
  • R represents 4 alkyl, etc.
  • a compound capable of generating a carbene for example, sodium trichloroacetate or sodium difluorochloroacetate at an elevated temperature (for example, about 100 ° C. to about 200 ° C.)
  • it can be produced by reacting with 50% sodium hydroxide in a chloroform form in the presence of a phase transfer catalyst such as triethylbenzylammonium chloride.
  • the compound of the formula (IV) in which W is a chlorine atom can be produced by hydrolyzing the compound obtained in the above step and then hydrolyzing it with thionyl chloride or the like.
  • the diazonium salt of aniline can be prepared by adding an aqueous solution of sodium nitrite to the hydrochloride or sulfate of aniline in water or a mixed solvent of water and an organic solvent kept at about ⁇ 10 to about 1 ° C. Can be manufactured.
  • Compounds of formula (III) in which R 6 is an optionally substituted 5- or 6-membered saturated or unsaturated heterocyclic group can likewise be prepared.
  • the compound of the formula (I) has an excellent control effect on pests such as pests and phytopathogenic microorganisms. Therefore, the compounds of the formula (I) are useful as pesticides.
  • the compounds of the formula (I) have an excellent control effect against pests, in particular agricultural pests, sanitary pests, storage pests, clothing pests and house pests.
  • pests include lepidopteran pests (eg, Lotus cutworm, Spodoptera, Acapulcum, Aomushi, Konaga, Japanese beetle, etc.),
  • Hemiptera pests eg, peach aphids, blue aphids, brown beetle power, stag beetle, brown beetle power, stag beetle, etc.
  • Coleoptera insects for example, rice worms, azuki worms, stalkworms, etc.
  • Diptera pests for example, houseflies, etc., plant parasitic nematodes, for example, cat flies, negusarecenti, rice singaresyu, pine moss, etc.
  • the compounds of the formula (I) have an excellent control effect against plant disease fungi. Therefore, the expression
  • the compounds (I) can be used as fungicides and fungicides.
  • plant disease fungi include microorganisms such as rice blast fungus, rice sheath blight fungus, cucumber anthracnose, cucumber downy mildew, cucumber powdery mildew, and wheat leaf rust.
  • the compounds of the formula (I) show excellent control activity against harmful weeds.
  • the compounds of formula (I) can be used as herbicides and herbicides.
  • the harmful weeds include plants such as Mehishino, Enokorogusa, Ooinuyu, Kosendangusa, American Sendangusa.
  • the compound of the formula (I) When the compound of the formula (I) is used as an active ingredient of a pesticide, the compound of the formula (I) Either use the compound as it is, or mix it with an appropriate solid carrier, liquid carrier, gaseous carrier, surfactant, dispersant, or other formulation aids to prepare emulsions, solutions, wettable powders, powders, granules, oils Use it in any dosage form such as aerosol, flowable and so on.
  • solid carrier examples include talc, benite, clay, kaolin, diatomaceous earth, bamboo silicate, white carbon, calcium carbonate and the like.
  • liquid carrier examples include alcohols such as methanol, n-hexanol and ethylene glycol; ketones such as acetone, methyl ethyl ketone and cyclohexanone; and aliphatic hydrocarbons such as n-hexane, kerosene and kerosene.
  • Aromatic hydrocarbons such as toluene, xylene and methylnaphthylene, ethers such as getyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, nitriles such as acetonitrile and isobutyronitrile, dimethylformamid Acid amides such as dimethylacetamide, vegetable oils such as soybean oil and cottonseed oil, dimethylsulfoxide, water and the like.
  • gas carrier examples include LPG, air, nitrogen, carbon dioxide, dimethyl ether and the like.
  • surfactants and dispersants for emulsification, dispersion, spreading, etc. include alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, and polyhydric alcohol esters. , Lignin sulfonate and the like can be used.
  • an adjuvant for improving the properties of the preparation for example, carboxymethyl cellulose, gum arabic, polyethylene glycol, calcium stearate and the like can be used.
  • the carrier, surfactant, dispersant, and auxiliary can be used alone or in combination as necessary.
  • the content of the active ingredient in the preparation is usually 1 to 75% by weight for emulsions, usually 0.3 to 25% by weight for powders, 1 to 90% by weight for wettable powders, and usually 0.1 to 90% by weight for granules. It can be 5 to 10% by weight.
  • the formulation according to the invention may contain other formulations such as other insecticides, fungicides, acaricides, herbicides, plant growth regulators, fertilizers and the like.
  • the preparation according to the present invention can be used as it is or after dilution.
  • the preparations of the present invention may be used in admixture with other preparations such as other insecticides, fungicides, acaricides, herbicides, plant growth regulators, fertilizers, and the like.
  • the present invention also provides a method for controlling pests, comprising treating an area to be protected from pests with an effective amount of a compound of formula (I) or a salt or solvate thereof. You.
  • the treatment of the protected area can be carried out by spraying on farmland or injecting into soil.
  • Ethyl methacrylate (40 ml) and triethylbenzylammonium chloride (2 g) were dissolved in black-mouthed form (200 ml), and heated at 40 ° C to 50% potassium hydroxide (220 g). Was slowly added dropwise, and after the addition was completed, the mixture was further stirred for 10 hours.
  • the reaction solution was poured into ice water, extracted with ethyl acetate, the ethyl acetate layer was washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give 2,2-dichloro-1-methylcyclohexane.
  • a crude product of ethyl propanecarboxylate (57 g) was obtained.
  • the ethyl acetate layer was washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product.
  • A indicates that the compound was synthesized according to the methods described in Synthesis Examples 1 and 2.
  • B indicates that the compound was synthesized according to the methods described in Synthesis Examples 3 and 4.
  • C indicates that the compound was synthesized according to the method described in Synthesis Example 5.
  • Compound of the present invention (Compound 1) 25% by weight
  • Compound of the present invention (Compound 1) 20% by weight
  • Test example 1 Pine moth control test
  • test compound diluted to 100 ppm with 50% acetone water (adding 20% 0.05%) to a cabbage leaf disk 5 cm in diameter in a plastic cup with a spray gun. Air dried. Release 10 second instar larvae in a cup Then, the animals were covered and kept in a constant temperature room at 25 ° C. Three days after the treatment, the larvae were observed for life and death, and the mortality was calculated.
  • test compound diluted to 200 ppm with 50% acetone water (tween en 20 0.05% added) was sprayed on a cabbage leaf disk 5 cm in diameter in a plastic cup with a spray gun and air-dried.
  • acetone water tween en 20 0.05% added
  • five third-stage larvae of the cutworm, Spodoptera litura were released, covered and kept in a constant temperature room at 25 ° C. Three days after the treatment, the larvae were observed for life and death, and the mortality was calculated.
  • Test example 3 Peach control test
  • a test compound diluted to 50 ppm with 50% acetone water (adding 0.05% of Tween 20%) to a 5 cm diameter cabbage leaf disk in a plastic cup was sprayed with a spray gun and air-dried.
  • Test example 4 Trifoliate control test
  • the following shows that the insecticidal rate showed an activity of 80% or more.
  • Test example 5 Rice blast control test
  • Control value (1 number of lesions in one treated area / number of lesions in untreated area) x 100
  • Test Example 6 Cucumber and disease control test
  • Diseased area is 1Z 4 or more and less than 1/2 of leaf area
  • Control value (1 disease severity in one treatment area / severity in untreated area) x 100
  • Test Example 7 Wheat leaf rust control test
  • Wheat seedlings (variety: Kanto No. 61), which were seeded in plastic pots containing culture soil, raised for about 14 days, and the third leaves were completely developed, were used as test plants.
  • harvested from wheat leaves which had been ill, prepared summer spore suspension (l ⁇ 5x l 0 6 Zml) was uniformly inoculated by spraying and allowed to stand for 24 hours in a room humidity 21 ° C.
  • the disease was then transferred to a climate chamber at 18 ° C at night and 22 ° C during the day to cause disease. 14 days after the inoculation, the diseased area of the third leaf was investigated, and the control value was calculated as in the case of cucumber and disease.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Pyridine Compounds (AREA)

Abstract

L'invention concerne des composés de formule générale (I) ainsi que des sels et des solvates de ceux-ci. Dans ladite formule (I), R?1, R2, R3, R4 et R5¿ représentent chacun hydrogène, halogéno, alkyle éventuellement substitué, ou phényle éventuellement substitué, à condition que tous les R?1, R2,R3, R4 et R5¿ ne représentent pas hydrogène ; R6 représente phényle éventuellement substitué ou un groupe hétérocyclique saturé ou insaturé à 5 à 6 éléments ; et R7 représente hydrogène, alkyle éventuellement substitué, alcoxycarbonyle éventuellement substitué, alcanoyle éventuellement substitué ou -CO-NR?11R12 (R11 et R12¿ représentant chacun alkyle éventuellement substitué ou alcoxy éventuellement substitué).
PCT/JP2000/004232 1999-06-28 2000-06-28 Derives hydrazones et pesticides WO2001000568A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU57040/00A AU5704000A (en) 1999-06-28 2000-06-28 Hydrazone derivatives and pest controllers
JP2001506981A JP4712261B2 (ja) 1999-06-28 2000-06-28 ヒドラゾン誘導体および有害生物防除剤

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP11/181250 1999-06-28
JP18125099 1999-06-28

Publications (1)

Publication Number Publication Date
WO2001000568A1 true WO2001000568A1 (fr) 2001-01-04

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Country Status (3)

Country Link
JP (1) JP4712261B2 (fr)
AU (1) AU5704000A (fr)
WO (1) WO2001000568A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006036480A1 (fr) * 2004-09-24 2006-04-06 Allergan, Inc. 4-(phenylmethyl et substitues de phenylmethyls)-imidazole-2-thiones agissant comme agonistes adrenergiques alpha2 specifiques
WO2006036512A3 (fr) * 2004-09-28 2006-05-04 Allergan Inc 4-benzyl-1,3-dihydro-imidazole-2-thiones non substitues et substitues utilises comme agonistes adrenergiques alpha2 specifiques ou selectifs et methodes d'utilisation
WO2014070897A1 (fr) * 2012-11-01 2014-05-08 Cooper Technologies Company Batterie de condensateurs isolée diélectrique

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02233654A (ja) * 1989-03-07 1990-09-17 Sumitomo Chem Co Ltd シアノ酢酸アミド誘導体を有効成分とする植物病害防除剤
JPH09143012A (ja) * 1995-11-21 1997-06-03 Nippon Soda Co Ltd 有害生物防除剤

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02233654A (ja) * 1989-03-07 1990-09-17 Sumitomo Chem Co Ltd シアノ酢酸アミド誘導体を有効成分とする植物病害防除剤
JPH09143012A (ja) * 1995-11-21 1997-06-03 Nippon Soda Co Ltd 有害生物防除剤

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006036480A1 (fr) * 2004-09-24 2006-04-06 Allergan, Inc. 4-(phenylmethyl et substitues de phenylmethyls)-imidazole-2-thiones agissant comme agonistes adrenergiques alpha2 specifiques
WO2006036512A3 (fr) * 2004-09-28 2006-05-04 Allergan Inc 4-benzyl-1,3-dihydro-imidazole-2-thiones non substitues et substitues utilises comme agonistes adrenergiques alpha2 specifiques ou selectifs et methodes d'utilisation
US7795292B2 (en) 2004-09-28 2010-09-14 Allergan, Inc. Unsubstituted and substituted 4-benzyl-1,3-dihydro-imidazole-2-thiones acting as specific or selective alpha2 adrenergic agonists and methods for using the same
US8178571B2 (en) 2004-09-28 2012-05-15 Allergan, Inc. Unsubstituted and substituted 4-benzyl-1,3-dihydro-imidazole-2-thiones acting as specific or selective alpha2 adrenergic agonists and methods for using the same
WO2014070897A1 (fr) * 2012-11-01 2014-05-08 Cooper Technologies Company Batterie de condensateurs isolée diélectrique

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JP4712261B2 (ja) 2011-06-29
AU5704000A (en) 2001-01-31

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