WO2001047903A1 - Composes de thiazolylcinnamonitrile, et insecticides et acaricides - Google Patents

Composes de thiazolylcinnamonitrile, et insecticides et acaricides Download PDF

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Publication number
WO2001047903A1
WO2001047903A1 PCT/JP2000/009224 JP0009224W WO0147903A1 WO 2001047903 A1 WO2001047903 A1 WO 2001047903A1 JP 0009224 W JP0009224 W JP 0009224W WO 0147903 A1 WO0147903 A1 WO 0147903A1
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WO
WIPO (PCT)
Prior art keywords
group
compound
atom
pests
compounds
Prior art date
Application number
PCT/JP2000/009224
Other languages
English (en)
Japanese (ja)
Inventor
Yasushi Shibata
Koichirou Aoyagi
Hidemitsu Takahashi
Renpei Hatano
Takao Iwasa
Original Assignee
Nippon Soda Co., 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 Nippon Soda Co., Ltd. filed Critical Nippon Soda Co., Ltd.
Priority to IL15015600A priority Critical patent/IL150156A0/xx
Priority to AU22250/01A priority patent/AU769975B2/en
Priority to BR0016797-5A priority patent/BR0016797A/pt
Priority to KR1020027008272A priority patent/KR20020067577A/ko
Publication of WO2001047903A1 publication Critical patent/WO2001047903A1/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
    • 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
    • A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Definitions

  • the present invention relates to a novel ditolyl thiazolyl cinnamate compound and an insecticide and acaricide containing the compound as an active ingredient.
  • WO95 / 29591 and JP-A-10-1585284 disclose a dicarboxylic acid cake derivative similar to the compound of the present invention. It is described as useful as an antifouling agent, but there is no description of its insecticidal activity.
  • An object of the present invention is to provide an insecticide and acaricide containing a ditolyl thiazolyl cinnamate compound as an active ingredient, which is effective and can be used safely.
  • the present invention provides a compound represented by the general formula (1):
  • X, X 2 and X 3 are each independently a halo gen atom, ct 3 alkyl group or - 3 haloalkyl group, n represents an integer of 0 or 1 to 3,
  • Y is a halogen atom, C, _ ⁇ alkyl group, C, - 4 alkoxy group or a C! _ Represents a no-alkyl group,
  • Upsilon 2 represents a hydrogen atom, a halogen atom, ci- 3 alkyl group, C - 4 alkoxy group or represents a ci- 3 haloalkyl group.
  • an insecticide characterized by containing the compound and / or one or more compounds that produce the compound in the insect body as active ingredients ⁇ It is an acaricide.
  • X j, x 2 and x 3 are halogen atoms such as fluorine, chlorine, bromine and iodine,
  • Ci- 3 alkyl groups such as methyl, ethyl, propyl, and isopropyl
  • C i such penta Furireo port Echiru - represents a 3 Ha port alkyl group
  • Is a halogen atom such as fluorine, chlorine, bromine, iodine,
  • C-alkyl groups such as methyl, ethyl, propyl, and isopropyl
  • Y 2 is a hydrogen atom, a halogen atom such as fluorine, chlorine, bromine, or iodine;
  • Ci-g alkyl groups such as methyl, ethyl, propyl, and isopropyl
  • Chloromethyl, fluoromethyl, promomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl Represents a 3- alkyl group such as chinole, trichloroethyl, trifluoroethylyl, and pentafluoroethyl.
  • the preferred substituent and ⁇ 2 each independently include a fluorine atom, a chlorine atom, a methyl group or a trifluormethyl group.
  • the compound of the present invention represented by the general formula (1) has two kinds of stereoisomers as follows, and three kinds of tautomers may exist. However, all of these isomers are included in the scope of the present invention.
  • the compound of the present invention can be used for controlling agricultural pests, sanitary pests, storage pests, clothing pests, house pests, and the like, and has an insecticidal, nymphalidic, larvicidal and ovicidal action.
  • the compound of the present invention having a substituent at the 2,6-position as compared with a known compound in which the phenyl group at the 4-position of the thiazole ring is an unsubstituted phenyl group or a 2-mono-substituted phenyl group.
  • X 1 and X 2 each independently represent a chlorine atom, a fluorine atom, a methyl group, or a trifluoromethyl group, and represents a chlorine atom, a fluorine atom, or a bromine atom.
  • Methyl group, methoxy group Compounds that are or trifluoromethyl groups are particularly excellent.
  • insecticidal and acaricide composition of the present invention are typical examples of pests to which the insecticidal and acaricide composition of the present invention can be applied.
  • Lepidopteran pests such as Hasmon nototo, Totoga, Tamanayaga, Aomushi, Tamanaginoku, Konaga, Chinococa kumonnomonaki, Chiyanomaki, Momomosiniga, Nashinhime Shingui, Mikanhamogiga , Chianohosoga, Kinmonhosoga, Myimaga, Chadokuga, Nikkameiga, Kobnomeiga, Yochichi Biankornborah, Amerikashirohitori, Sujimadarameiga, Heliotis , Helicoverpa, Agrotis, Iga, Kodlinga, Peta mimushi, etc.
  • Hemiptera pests for example, peach aphid, peta aphid, Nisedai kombi, wheat bilea aphid, scorpion beetle, stag beetle, yano nekai garashi, kukonaka garamushi, konshika karajimi, jiminami konami, tobacco Pear-dung beetles, rubbing powers, hummingbird powers, sage loungers, tsumaguro-kobai, etc.
  • Coleopteran pests such as Lepidoptera, Beetle, Beetle, Beetle, Beetle, Beetle, Azukizomushi, Mamekogane, Himekogane, Giabrotica, Tanokoshibanmushi, Hirakikushimushi. Pine wood beetle, pine wood beetle, agliotis genus, rainbow trout, coconut, pomegranate, etc.
  • Diptera insect pests for example, house flies, oak fly, sentinflies, perfume flies, citrus flies, flies, flies, flies, flies, frog flies, flies ,
  • Thistle pests for example, southern yellow thistle, cyano thistle, etc.
  • Hymenopteran pests for example, Dipteria japonicus, Japanese hornet, Dermatophagoides, Orthopterous pests, for example, cockroach cockroaches, Scarab cockroaches, Black cockroaches, etc., Termite pests, for example, Dermatophagoides, Jamatosiroa, etc.
  • Lepidopteran pests eg, flea flea, lice Lice pests, eg, human lice, mites, eg, Namihadani, Nisenamihadani, Kanzahadani, Mikanhada 2. Lingo red mite, mikansavidani, lingosavidani, chianohokoridani, brevipalpas, teoteranikas, robinne mite, stag beetle mites, kona hyodo mite, oshima ticks, phloem ticks, etc. ,
  • Plant-parasitic nematodes for example, Saccharomyces cerevisiae, Negusacenti, Soybean ciscenta, Rice singacenti, Matsunozai senchiu and the like.
  • the pests to which the compound of the present invention is preferably applied include lepidopteran pests, Hemiptera pests, Coleoptera pests, Azamazuma pests, and two-legged pests.
  • lepidopteran pests Preferable are lepidopteran pests, Hemiptera pests, Thistle pests, and two species.
  • the compound of the present invention has an excellent insecticidal and acaricidal effect against not only susceptible strains but also pests of organic phosphorus, carbamate, and pyrethide-resistant strains, and mites of acaricide-resistant strains. It is a drug.
  • the compound of the present invention is a highly safe drug with little phytotoxicity, low toxicity to fish and warm-blooded animals.
  • the compound of the present invention can be produced, for example, as follows.
  • L is Nono b Gen atom, C i-6 alkoxy group, Fueno alkoxy group, 1 Represents a leaving group such as an imidazolyl group, a 1-birazolyl group, a p-toluenesulfonyloxy group, a methansulfonyloxy group, or a trifluoromethansulfonyloxy group.
  • Examples of the base used in this reaction include alkali metal hydroxides such as sodium hydroxide and sodium hydroxide, and carbonates such as sodium carbonate and potassium carbonate.
  • Organic metals such as butyllithium and lithium diisopropylamine (LDA), and organic bases such as triethylamine, diisopropylethylamine and pyridine.
  • Solvents that can be used include N, N-dimethylformamide (DMF), dimethylsulfoxide (DMSO), tetrahydrofuran (THF), and acetonitrile. , Hexanemethyl amide (HMPA), benzene, toluene, dichloromethan, chloroform, carbon tetrachloride, etc. can be used.
  • the reaction temperature is preferably in the range from 178 to the boiling point of the solvent used.
  • the compound of the present invention When the compound of the present invention is actually applied as an insecticide or acaricide, it can be used in a pure form without adding other components.
  • forms that can be taken by general pesticides for the purpose of using them as pesticides such as wettable powders, granules, powders, emulsions, aqueous solvents, suspensions, flowable powders, and wettable powders It can also be used at
  • additives and carriers include soybean grains, vegetable powders such as flour, diatomaceous earth, apatite, gypsum, talc, bentonites, pyrophyllites, ku Mineral fine powders such as leh, organic and inorganic compounds such as sodium benzoate, urea, and sodium sulfate are used.
  • kerosene, xylene and petroleum aromatic hydrocarbons, cyclohexane, cyclohexanone, DMF, DMSO, alcohol, acetone, trichloroethylene , Methyl isoptyl ketone, mineral oil, vegetable oil, Water or the like can be used as a solvent.
  • a surfactant can be added as necessary to obtain a uniform and stable form in these preparations.
  • the surfactant is not particularly limited. Examples of the surfactant include alkyl phenyl ether to which polyoxyethylene is added, alkyl ether to which polyoxyethylene is added, higher fatty acid ester to which polyoxyethylene is added, and polyoxyethylene.
  • Nonionic surfactants such as added sorbitan higher fatty acid esters, polyoxyethylene added tristyl phenyl ether, etc., ester sulfates of alkylphenyl ethers added with polyoxyethylene, alkylbenzene sulfonates , Higher alcohol sulfates, alkyl naphthalene sulfonates, polycarboxylates, lignin sulfonates, formaldehyde condensates of alkyl naphthalene sulfonates, isobutylene monoanhydride Polymer And the like.
  • the amount of the active ingredient (compound of the present invention) in the preparation is preferably about 0.01 to 90% by weight, and more preferably about 0.05 to 85% by weight.
  • the obtained wettable powder, emulsion,! BS » ⁇ , flowables are used as a suspension or emulsion by diluting to a predetermined concentration with water, and dusts and granules are used as they are applied to plants or soil.
  • the compound of the present invention is sufficiently effective alone, but it may be used in combination with one or more of various fungicides, insecticides, acaricides, or synergists. Can also,
  • fungicides insecticides, acaricides, and plant growth regulators that can be used in combination with the compound of the present invention are shown below.
  • Captan Forpet, Thiuram, Jiram, Zineb, Manneb. Mancozeb, Brovineb, Polycarbamate, Chlorotalone, kind Isen, Captahor, Iblogion, Procymidone, Vinclozolin, Fluoroymide, Thymoxanil, Mepronil, Flutolanil, Pensiclone, Oxycarbinone, Josetylaluminium, Propamocarb, Triazimehon, Triazimenol, Bropiconazol, Diclobutrazole, bitertanol, hexaconazole, microclothani ⁇ , flusilazole, etaconazole, fluorotrimazole, Lutriaphen, Benconazole, Diniconazole, Cyproconazoles, Fenarimole, Triflumizole, Prochloraz, Imazalil, Drifazolate, Tridemorph , Fenpropimorph, trifolin, peti
  • Pyrethroid insecticides Permethrin, Cypermethrin, Delta Meslin, Fembrelate, Fembro Trin, Piletrin, Allethrin, Tetrameth Lin, Resmetrine, Dimethrin, Prono Screen, Pheno Trin, Protoline, Furuno Line, Cyfuru Screen, Shino Screen Linole, phenolic linen, etfenprox, cycloprolin, torametrin, silafluorene, acrinatrin, etc.
  • Plant growth regulator Plant growth regulator
  • Gibberellins eg, gibberellin A3, gibberellin A4, gibberellin A7, IAA, NA A, and the like.
  • Example 1 [4— (2,6-Difluorophenyl) _2—thiazolyl] -1-3—hydroxy-1 2'—trifluorometyl-cinnamic acid
  • Table 1 shows typical examples of the compound of the present invention which can be produced in this manner.
  • the abbreviation Me in the table represents methyl.
  • Example 2 wettable powder
  • Dioctyl sulfosuccinate tonadium salt 4 parts Eight or more parts of sodium ligninsulfonate were uniformly mixed and finely pulverized to obtain a hydrate of 40% of the active ingredient.
  • the above mixture was uniformly mixed and finely ground, and then an appropriate amount of water was added and kneaded, the mixture was made into a clay, granulated, and dried to obtain a wettable powder with an active ingredient of 40%.
  • the compound was diluted with water so that the compound concentration became 125 ppm.
  • Corn leaves were immersed in the solution for 30 seconds, air-dried, and then placed in a petri dish containing five second instar larvae.
  • the glass lid was put on the container, and it was placed in a constant temperature room at a temperature of 25 t and a humidity of 65%. After 6 days, the insecticidal rate was examined. Two iterations.
  • the insecticidal rate of the control compound A was 0%, and the insecticidal rate of chlordimeform used as a control was 40%.
  • insecticidal rates of the following known compounds used as controls were as follows.
  • Control compound A 44%
  • Control compound B 0%

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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)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des composés représentés par la formule générale (I) ; ainsi que des produits antiparasitaires contenant chacun, comme principe actif, un ou plusieurs éléments choisis parmi lesdits composés : Dans ladite formule (I), X1, X2 et X3 représentent chacun indépendamment un halogéno, un C1-3alkyle ou un C1-3haloalkyle ; n désigne un entier compris entre 0 et 3 ; Y1 représente un halogéno, un C1-3alkyle, un C1-4alcoxy ou un C1-3haloalkyle ; et Y2 représente un hydrogène, un halogéno, un C1-3alkyle, un C1-4alcoxy ou un C1-3haloalkyle.
PCT/JP2000/009224 1999-12-27 2000-12-26 Composes de thiazolylcinnamonitrile, et insecticides et acaricides WO2001047903A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
IL15015600A IL150156A0 (en) 1999-12-27 2000-12-26 Thiazolylcinnamonitrile compounds and insecticides and miticides
AU22250/01A AU769975B2 (en) 1999-12-27 2000-12-26 Thiazolylcinnamonitrile compounds and insecticides and miticides
BR0016797-5A BR0016797A (pt) 1999-12-27 2000-12-26 Composto, inseticida e acaricida
KR1020027008272A KR20020067577A (ko) 1999-12-27 2000-12-26 티아졸릴신나모니트릴 화합물, 및 살충제 및 살비제

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP37058299 1999-12-27
JP11/370582 1999-12-27

Publications (1)

Publication Number Publication Date
WO2001047903A1 true WO2001047903A1 (fr) 2001-07-05

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PCT/JP2000/009224 WO2001047903A1 (fr) 1999-12-27 2000-12-26 Composes de thiazolylcinnamonitrile, et insecticides et acaricides

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KR (1) KR20020067577A (fr)
CN (1) CN1413201A (fr)
AU (1) AU769975B2 (fr)
BR (1) BR0016797A (fr)
IL (1) IL150156A0 (fr)
WO (1) WO2001047903A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101906079A (zh) * 2010-07-23 2010-12-08 浙江工业大学 噻唑基丙烯腈酯类化合物、制备方法及其应用

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101215269B (zh) * 2007-12-29 2010-06-09 浙江工业大学 一种2-噻唑基丙烯腈类化合物及其合成方法与应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5392769A (en) * 1977-01-26 1978-08-15 Schering Ag Thiazolylcinnamate nitrile process for preparing same and vermicide containing same
GB2051052A (en) * 1979-05-17 1981-01-14 Schering Ag Insecticidally active thiazolylidene-oxo-propionitriles and their manufacture and use
EP0189960A2 (fr) * 1985-02-01 1986-08-06 Shell Internationale Researchmaatschappij B.V. Dérivés insecticides du 1,3-thiazole
WO1997040009A1 (fr) * 1996-04-25 1997-10-30 Nissan Chemical Industries, Ltd. Derives ethyleniques et agents pesticides
WO2000017174A1 (fr) * 1998-09-17 2000-03-30 Nippon Soda Co., Ltd. Thiazolylcinnamonitriles et agents antiparasitaires

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5392769A (en) * 1977-01-26 1978-08-15 Schering Ag Thiazolylcinnamate nitrile process for preparing same and vermicide containing same
GB2051052A (en) * 1979-05-17 1981-01-14 Schering Ag Insecticidally active thiazolylidene-oxo-propionitriles and their manufacture and use
EP0189960A2 (fr) * 1985-02-01 1986-08-06 Shell Internationale Researchmaatschappij B.V. Dérivés insecticides du 1,3-thiazole
WO1997040009A1 (fr) * 1996-04-25 1997-10-30 Nissan Chemical Industries, Ltd. Derives ethyleniques et agents pesticides
WO2000017174A1 (fr) * 1998-09-17 2000-03-30 Nippon Soda Co., Ltd. Thiazolylcinnamonitriles et agents antiparasitaires

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101906079A (zh) * 2010-07-23 2010-12-08 浙江工业大学 噻唑基丙烯腈酯类化合物、制备方法及其应用
CN101906079B (zh) * 2010-07-23 2012-07-18 浙江工业大学 噻唑基丙烯腈酯类化合物、制备方法及其应用

Also Published As

Publication number Publication date
IL150156A0 (en) 2002-12-01
BR0016797A (pt) 2002-11-05
AU2225001A (en) 2001-07-09
AU769975B2 (en) 2004-02-12
KR20020067577A (ko) 2002-08-22
CN1413201A (zh) 2003-04-23

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