Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ester doai
Reexamination Certificate
1999-10-15
2001-09-25
Levy, Neil S. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ester doai
C424S405000, C424S409000
Reexamination Certificate
active
06294576
ABSTRACT:
The present invention relates to a pyrethroid compound and a composition for controlling pest which contains said compound as an active ingredient.
It has been known that some pyrethroid compounds containing an alcohol moiety derived from a certain fluorine-substituted benzyl alcohol exhibit an insecticidal activity (EP-A-54360). These compounds, however, are not always sufficient in practical pest-controlling effect as an active ingredient of compositions for controlling pest.
In order to find a pyrethroid compound having a practically pest-controlling effect, the present inventors earnestly investigated and consequently found that 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylate represented by the formula shown below has an excellent pest-controlling effect and is very effective particularly in preventing domestic epidemics, whereby the present invention has been accomplished.
Thus, the present invention relates to 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylate (hereinafter referred to as the present compound) represented by the formula:
and a composition for controlling pest which contains the present compound as an active ingredient.
The present compound has stereoisomers relative to the asymmetric carbon atom on the cyclopropane ring and includes any active one of these stereoisomers and mixtures thereof.
In the present compound,(1R)-isomer or (1R)-enriched isomers are preferable in view of the excellent pesticidal activity. Moreover, (1R)-trans-isomer or (1R)-trans-enriched isomers are particularly preferable for controlling pests for preventing domestic epidemics.
The present compound can be produced, for example, by reacting an alcohol compound represented by the formula:
with a carboxylic acid compound represented by the formula:
or a reactive derivative (e.g., acid halide or acid anhydride) of said carboxylic acid compound.
The reaction is usually carried out in a solvent in the presence of a condensing agent or a base.
The condensing agent includes, for example, dicyclohexylcarbodiimide and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride.
The base includes, for example, organic bases such as triethylamine, pyridine, N,N-diethylaniline, 4-dimethylaminopyridine and diisopropylethylamine.
The solvent includes, for example, hydro-carbons such as benzene, toluene and hexane; ethers such as diethyl ether and tetrahydrofuran; and halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane and chlorobenzene.
The reaction time ranges usually from 5 minutes to 72 hours.
The reaction temperature ranges usually from −20° C. to +100° C. (or from −20° C. to the boiling point of the solvent in the case where the boiling point of the solvent is lower than +100° C.), preferably from −5° C. to +100° C. (or from −5° C. to the boiling point of the solvent in the case where the boiling point of the solvent is lower than +100° C.).
Although the molar ratio of the alcohol compound to the carboxylic acid compound or its reactive derivative can be selected without any limitation, it is preferable to carry out the reaction by using them in an approximate molar ratio of 1:1.
The condensing agent or the base can be used in any amount of usually 1 mole or more, preferably 1 mole to 5 moles, per mole of said alcohol compound. The condensing agent or the base is appropriately chosen depending on the kind of said carboxylic acid compound or its reactive derivative to be reacted.
After completion of the reaction, the reaction solution is poured into water and then subjected to conventional work-up procedures such as extraction with an organic solvent, concentration and the like to obtain the present compound. Also, the present compound can be purified by operations such as chromatography, distillation and the like.
The above-mentioned alcohol compound and carboxylic acid compound can be produced according to, for example, the process disclosed in EP-A-54360.
Specific examples of the pests on which the present compound has a controlling effect are the following arthropods:
Lepidoptera
Pyralidae (pyralid moths) such as
Chilo suppressalis
(rice stem borer),
Cnaphalocrocis medinalis
(rice leafroller) and
Plodia interpunctella
(Indian meal moth); Noctuidae such as
Spodoptera litura
(tobacco cutworm),
Pseudaletia separata
(rice armyworm) and
Mamestra brassicae
(cabbage armyworm); Pieridae such as
Pieris rapae crucivora
(common cabbageworm); Tortricidae (tortricid moths) such as Adoxophyes spp.; Carposinidae; Lyonetiidae (lyonetiid moths); Lymantriidae (tussock moths); Antographa spp.; Agrotis spp. such as
Agrothis segetum
(turnip cutworm)
and Agrothis ipsilon
(black cutworm); Helicoverpa spp.; Heliothis pps.;
Plutella xylostella
(diamondback moth);
Parnara guttata
(rice skipper);
Tinea pellionella
(casemaking clothes moth);
Tineola bisselliella
(webbing clothes moth); etc.
Diptera
Culex spp. such as
Culex pipiens pallens
(common mosquito)and
Culex tritaeniorhynchus;
Aedes spp. such as
Aedes aegypti
and
Aedes albopictus;
Anopheles spp. such as
Anopheles sinensis;
Chironomidae (midges); Muscidae such as Musca domestica (housefly),
Muscina stabulans
(false stablefly) and
Fannia canicularis
(little housefly); Calliphoridae; Sarcophagidae; Anthomyiidae (anthomylid flies) such as
Delia platura
(seedcorn maggot) and
Delia antiqua
(onion maggot); Tephritidae (fruit flies); Drosophilidae (small fruit flies, vinegar flies); Psychodidae (moth flies, sand flies); Phoridae; Simuliidae (black flies); Tabanidae; Stomoxyidae (stable flies); biting midges; etc.
Dictyoptera
Blattella germanica
(German cockroach),
Periplaneta fuliginosa
(smokybrown cockroach),
Periplaneta americana
(American cockroach),
Periplaneta brunnea
(brown cockroach),
Blatta orientalis
(oriental cockroach), etc.
Hymenoptera
Formicidae (ants); Vespidae (hornets); Bethylidae (bethylid wasps); Tenthredinidae (sawflies) such as
Athalia rosae ruficornis
(cabbage sawfly); etc.
Siphonaptera
Ctenocephalides canis, Ctenocephalides felis, Pulex irritans,
etc.
Anoplura
Pediculus humanus, Phthirus pubis, Pediculus humanus
var.
capitis, Pediculus humanus
var.
corporis,
etc.
Isoptera termites
Reticulitermes speratus, Coptotermes formosanus
(Formosan subterranean termite), etc.
Hemiptera
Delphacidae (planthoppers) such as
Laodelphax striatellus
(small brown planthopper),
Nilaparvata lugens
(brown planthopper) and
Sogatella furcifera
(white-backed rice planthopper); Deltocephalidae (leaf-hoppers) such as
Nephotettix cincticeps
(green rice leafhopper) and
Nephotetti virescens
(green rice leafhopper); Aphididae (aphids); Pentatomidae (bugs); Aleyrodidae (whiteflies); Coccidae (scales); Tingidae (lace bugs); Psyllidae (psyllids); etc.
Coleoptera
Attagenus unicolor; Anthrenus verbasci
(varied carpet beetle); corn rootworms such as
Diabrotica virgifera
(western corn rootworm) and
Diabrotica undecimpunctaca howardi
(southern corn rootworm); Scarabaeidae (scarabs) such as
Anomala cuprea
(cupreous chafer) and
Anomala rufocuprea
(soybean beatle); Curculionidae (weevils) such as
Sitophilus zeamais
(maize weevil),
Lissorhoptrus oryzophilus
(ricewater weevil),
Anthonomus grandis grandis
(boll weevil) and
Callosobruchus chinensis
(adzuki bean weevil); Tenebrionidae (darkling beetles) such as
Tenebrio molitor
(yellow mealworm) and
Tribolium castaneum
(red fluor beetle); Chrysomelidae (corn rootworms) such as
Oulema oryzae
(rice leaf beetle),
Phyllotreta striolata
(striped flea beetles) and
Aulacophora femoralis
(cucurbit leaf beetle); Anobiidae; Epilachna spp. such as
Henosepilachna vigintioctopunctata
(twenty-eight-spotted ladybirds); Lyctidae (powder post beetles); Bostrychidae (false powder post beetles); Cerambycidae;
Paederus fuscipes
(robe beetle); etc.
Thysanoptera (thrips)
Thrips palmi, Frankliniella occidentalis
(western flower thrips), Thrips
hawaiiensis
(flower thrips), etc.
Orthoptera
Gryl
Levy Neil S.
Stevens, Davis, Miller & Moscher, LLP
Sumitomo Chemical Company Limited
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