Pyrone compounds and there use

Details Pyrone compounds and there use Pyrone compounds and there use

2002-05-02

2003-01-21

Owens, Amelia (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C549S291000

Reexamination Certificate

active

06509299

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to pyrone compounds and their pesticidal use.
BACKGROUND ART
JP51-19126A discloses that some pyrone compounds have insecticidal/acaricidal activity. However, their compounds are not satisfactorily effective for controlling harmful pests.
SUMMARY OF THE INVENTION
The present invention provides a compound given by formula
wherein R represents a trifluoromethyl group, hydrogen atom or methyl group, a pesticidal composition comprising it as an active ingredient and a method for controlling pests comprising applying it to pests or a place where pests inhabit.
The present compound has an excellent pesticidal activity.
DISCLOSURE OF THE INVENTION
A process for producing the present compound is explained below.
The present compound can be produced by the method given by the scheme below, namely reaction of 4-hydroxy-6-methyl-2-pyrone given by formula (2) with a carboxylic acid given by formula (3):
wherein R has the same meaning above.
The reaction is usually carried out in a solvent in the presence of a condensing agent (e.g. dicyclohexylcarbodiimide) and 4-dimethylaminopyridine.
Examples of the solvent to be used for the reaction include aliphatic hydrocarbons such as hexane, heptane, octane and nonane; aromatic hydrocarbons such as toluene, xylene and mesitylene; halogenated hydrocarbons such as chlorobenzene, dichlorobenzene and benzotrifluoride; ethers such as diisopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether and diethylene glycol dimethyl ether; acid amides such as N,N-dimethylformamide and N,N-dimethylacetamide; sulfur-containing solvents such as dimethyl sulfoxide and sulfolane; and mixtures thereof.
In the reaction, the amount ratio of the compound given by formula (3) is 0.7 to 1.5 moles based on 1 mole of the compound given by formula (2).
The amount ratio of the reagents is 1 to 5 moles of the condensing agent and 0.01 to 1 mole of 4-dimethylaminopyridine based on 1 mole of the compound given by formula (2).
The reaction temperature is usually within a range from 0° C. to 100° C., and the reaction time is usually within a range from 1 to 48 hours though it depends on the reaction temperature.
After the completion of the reaction, the reaction mixture can be, for example, subjected to a filtration, washing the filtrate with an acidic water, drying and then concentration, optionally purification such as chromatography, to give the present compound as an isolated product.
Examples of the pests against which the present compound exhibits a control effect include the following arthropods: Hemipteran pests: Delphacidae (planthoppers) [e.g.
Laodelphax striatellus
(small brown planthopper),
Nilaparvata lugens
(brown planthopper) and
Sogatella furcifera
(white-backed rice planthopper)], Deltocephalidae (leafhoppers) [e.g.
Nephotettix cincticeps, Nephotettix virescens
and
Recilia dorsalis
], Aphididae (aphids), stinkbugs, Aleyrodidae (whiteflies), scales, Tingidae (lace bugs) and Psyllidae (suckers);
Lepidopteran pests: Pyralidae [e.g.
Chilo suppressalis
(rice stem borer),
Cnaphalocrocis medinalis
(rice leafroller) and
Plodia interpunctella
(Indian meal moth)], Noctuidae [e.g.
Spodoptera litura
(tobacco cutworm),
Pseudaletia separata
(rice armyworm),
Mamestra brassicae
(cabbage armyworm), Plusiinae, Agrotis spp. containing
Agrotis segetum
(turnip cutworm) and
Agrotis ipsilon
(black cutworm), Helicoverpa spp. and Heliothis spp.], Pieridae [e.g.
Pieris rapae],
Tortricidae [e.g. Adoxophyes spp.], Carposinidae, Lyonetiidae, Lymantriidae, Yponameutidae [e.g.
Plutella xylostella
], Hesperiidae [e.g.
Parnara guttata
], Tineidae [e.g.
Tinea translucens
(casemaking clothes moth) and
Tineola bisselliella
(webbing clothes moth)];
Dipteran pests: Culex spp. [e.g.
Culex pipiens pallens
and
Culex tritaeniorhynchus]
, Aedes spp. [e.g.
Aedes aegypti
(yellow fever mosquito) and
Aedes albopictus
], Anopheles spp. [e.g.
Anopheles sinensis
], Chironomidae (midges), Muscidae [e.g.
Musca domestica
(housefly),
Muscina stabulans
(false housefly) and
Fannia canicularis
(little house fly)], Calliphoridae, Sarcophagidae, Anthomyiidae [e.g.
Delia platura
(seedcorn maggot) and
Delia antiqua
(onion maggot)], Tephritidae (fruit flies), Drosophilidae (vinegar flies), Psychodidae (sand flies), Tabanidae, Simuliidae (black flies), Stomoxyidae (stable flies), Phoridae and Ceratopogonidae (biting midges);
Coleopteran pests: corn rootworms [e.g.
Diabrotica virgifera virgifera
(western corn rootworm) and
Diabrotica undecimpunctata howardir
(southern corn rootworm)], Scarabaeidae [e.g.
Anomala cuprea
and Anomala rufocuprea], Curculionidae (weevils) [e.g.
Sitophilus zeamais
(maize weevil) and
Lissorhoptrus ozyzophilus
(ricewater weevil), Dermestidae [e.g.
Authrenus verbasci
and
Attagenus unicolor japonicus
], Tenebrionidae (darkling beetles) [e.g.
Tenebrio molitor
(yellow mealworm) and
Tribolium castaneum
(red flour beetle)], Chrysomelidae (leaf beetles) [e.g.
Oulema oryzae
(rice leaf beetle),
Phyllotreta striolata
(striped flea beetle) and
Aulacophora femoralis
(cucurbit leaf beetle), Anobiidae, Coccinellidae (ladybirds). [e.g.
Epilachna vigintioctopunctata
], Lyctidae (powderpost beetles), Bostrychidae, Cerambycidae and Staphylinidae [e.g.
Paederus fuscipes];
Dictyopteran pests:
Blattella gezmanica
(German cockroach),
Periplaneta fuliginosa
(smokybrown cockroach),
Periplaneta americana
(American cockroach),
Periplaneta brunnea
(brown cockroach) and
Blatta orientalis
and so on;
Thysanopteran pests: Thripidae [e.g.
Thrips palmi, Frankliniella occidentalis
(western flower thrips) and
Thrips hawaiiensis
(flower thrips)];
Hymenopteranpests: Formicidae (ants), Vespidae [e.g. hornets and long-legged wasps], Bethylidae and Tenthredinidae (sawflies) [e.g.
Athalia japonica
(cabbage sawfly)];
Orthopteran pests: Gryllotalpidae (mole crickets) and Acrididae (grasshoppers);
Siphonapteran pests:
Ctenocephalides canis
(dog flea),
Ctenocephalides felis
(cat flea) and
Pulex irritans
(human flea);
Anopluran pests:
humanus corporis, Pediculus capitis
and
Phthirus pubis
(crab louse);
Isopteran pests;
Reticulitezmes speratus
and
Coptotezmes fozmosanus;
Acarina pests: Tetranychidae (spider mites) [e.g.
Tetranychus cinnabarinus
(carmine spider mite),
Tetranychus urticae
(two-spotted spider mite),
Tetranychus kanzawai
(Kanzawa spider mite),
Panonychus citri
(citrus red mite) and
Panonychus ulmi
(European red mite)], Ixodidae [e.g.
Boophilus microplus
and
Haemaphysalis longiconis
], Acaridae [e.g.
Tyrophagus putrescentiae
(copra mite) and
Aleuroglyphus ovatus
], Dermanyssidae [e.g.
Dermatophagoides farinae
(American house dust mite) and
Dermatophagoides ptrenyssnus
], Glycyphagidae [e.g.
Glycyphagus privates, Glycyphagus domesticus
and
Glycyphagus destructor
], Cheyletidae [e.g.
Cheyletus malaccensi
and
Cheyletus fortis
], Tarsonemidae, Chortoglyphus spp. and Haplochthonius spp.;
Isopoda pests: wood louse [e.g.
Porcellio scaber
and
Porcellionides pruinosus
] and pill-bugs [e.g.
Armadillidium vulgare].
The pesticidal composition of the present invention comprises the present compound and an inert carrier, such as solid carrier, liquid carrier, gaseous carrier and/or bait material (poison bait material). The present compound may be impregnated with a base material (e.g. porous ceramic board, non-woven cloth, paper, mosquito-coil base). Further, the pesticidal composition of the present invention optionally comprises a surfactant or the other auxiliary to be formulated to oil solutions, emulsifiable concentrates, wettable powders, flowable formulations, granules, dusts, aerosols, foggings, heating fumigants, smokings

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