Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ester doai
Reexamination Certificate
1999-05-07
2002-07-23
Levy, Neil S. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ester doai
C424S405000
Reexamination Certificate
active
06423745
ABSTRACT:
BACKGROUND OF THE INVENTION
It has been known that, for example, esters of haloalkenylcyclopropanecarboxylic acids and 2-methyl-4-oxo-3-(2-propynyl)-cyclopent-2-enyl alcohol have an insecticidal activity, see GB-2055822-A.
Application of such compositions containing the above esters, however, is often unavoidably limited not only by their controlling effect but also by their safety, depending on the application conditions. In particular, usually, compositions for controlling pest for preventing epidemics are used mainly in a limited space in a living environment and hence are required to have a desirable insecticidal or repellent activity as well as a marked harmlessness to mammals such as human beings, livestock and pets.
BRIEF SUMMARY OF THE INVENTION
In recognition of the situation, the present inventors have earnestly investigated and consequently found that a specific optically active trans-form of 2-methyl-4-oxo-3-(2-propynyl)-cyclopent-2-enyl 3-(2,2-dichlorovinyl)-2, 2-dimethylcyclopropanecarboxylate is a compound excellent in controlling effect on pest and harmlessness to mammals, to accomplish the present invention.
Thus, the present invention relates to (S)-2-methyl-4-oxo-3-(2-propynyl)-cyclopent-2-enyl (1R)-trans-3-(2,2-dichlorovinyl)-2, 2-dimethylcyclopropanecarboxylate (hereinafter referred to as the present compound) represented by the formula:
and a composition for controlling pest containing the present compound as an active ingredient.
The present compound can be produced, for example, by reacting (S)-2-methyl-4-oxo-3-(2-propynyl)-cyclopent-2-enyl alcohol (hereinafter referred to as the alcohol compound) represented by the formula:
with (1R)-trans-3-(2,2-dichlorovinyl)-2, 2-dimethylcyclopropanecarboxylic acid (hereinafter referred to as the 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 (DCC) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (WSC).
The base includes, for example, organic bases such as triethylamine, pyridine, N,N-diethylaniline, 4-dimethylaminopyridine and diisopropylethylamine.
The solvent includes, for example, hydrocarbons such as benzene, toluene and hexane; ethers such as diethyl ether, and tetrahydrofuran; and halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane.
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 carboxylic acid compound or its reactive derivative to the alcohol compound 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 an arbitrary ratio to the alcohol compound, and is preferably used in an amount of 1 mole to 5 moles per mole of the alcohol compound.
The present compound can be obtained by subjecting the reaction solution after completion of the reaction to conventional after-treatments such as extraction with an organic solvent and concentration. If necessary, it can be further purified by conventional operations such as chromatography, distillation and recrystallization.
The alcohol compound can be produced according to, for example, the process disclosed in U.S. Patent No. 4,571,436, etc. The carboxylic acid compound can be produced according to, for example, the process disclosed in JP-A-4-234991, etc.
Examples of pests on which the present compound has controlling effect are the arthropods given below. Because the present compound can be used as an active ingredient of a composition for controlling the following arthropods and in particular is superior in safety factor, it is especially effective as the active ingredient of a composition for controlling pest for preventing epidemics, which is required to have a high safety to mammals.
Lepidoptera
Pyralidae (pyralid moths) such as
Chilo suppressalis
(rice stem borer),
CnaDhalocrocis 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.; Acrotis spp. such as
Agrothis segetum
(turnip cutworm) and
Agrothis ipsilon
(black cutworm); Helicoverpa spp.; Heliothis spp.;
Plutella xylostella
(diamondback moth);
Parnara guttata
(rice skipper);
Tinea translucens
(casemaking clothes moth);
Tineola bisselliella
(webbing clothes moth);
Plodia interpunctella
(Indian meal moth); etc.
Diptera
Culex spp. such as
Culex pipiens pallens
(common mosquito)and
Culex tritaeniorhvnchus
; 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 antigua
(onion maggot); Tephritidae (fruit flies); Drosophilidae (small fruit flies, vinegar flies); Psychodidae (moth flies, sand flies); 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
, etc.
Isoptera Termites
Reticulitermes spereratus, Coptotermes formosanus
(Formosan subterranean termite), etc.
Acarina (Mites and Ticks)
Pyroglyphidae such as
Dermatophagoides farinae
and
Dermatophagoides pteronyssinus
; Acaridae such as
Tyrophagus putrescentiae
Schrank (mold mite, copra mite, forage mite) and
Aleurogalyphus ovatus
Troupeau (brown legged grain mite); Glycyphagidae such as
Glycyphagus privatus, Glycyphagus domesticus
and
Glycyphagus destructor
Schrank (groceries mite); Cheyletidae such as
Cheyletus malaccensis
and
Cheyletus moorei
; Tarsonemidae; Chrtoglyphus; Oribatei; Tetranychidae (spider mites) such as
Tetranychus urticae
(two-spotted spider mite),
Tetranvchus kanzawai
(Kanzawa spider mite),
Panonychus citri
(citrus red mite) and
Panonychus ulmi
(European red mite); Ixodidae such as
Haemaphysalis longicornis
; 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
Nephotettix 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
Ishiwatari Takao
Otaka Ken
Levy Neil S.
Stevens Davis Miller & Mosher L.L.P.
Sumitomo Chemical Co,. Ltd.
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