Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-04-11
2003-09-30
Pak, John (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S875000, C514S876000, C514S919000, C424SDIG001, C424SDIG001
Reexamination Certificate
active
06627654
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to an arthropod-controlling composition comprising a specific &agr;-pyrone compound as an active ingredient.
BACKGROUND ART
Many arthropod-controlling compositions are on the market at present. However, the objected harmful arthropods have many kinds and the situations for controlling them are in many ways. Therefore, the arthropod-controlling composition having practically high effectiveness and safety is desired.
Though pyrethroid pesticides having rapid knock-down efficacy are excellent agents for controlling harmful insects, progress of pyrethroid resistance to some insects has been reported in various places recently. Under these circumstances, non-pyrethroid compounds having excellent knock-down efficacy are earnestly desired.
On the other hand, it is known that some &agr;-pyrone compounds are effective for controlling harmful acarina and insects such as housefly in Japanese Unexamined Patent Publication No. sho-51-19126. However, the compounds described in the publication do not necessarily give a sufficient effect.
SUMMARY OF THE INVENTION
The present invention provides an arthropod-controlling composition comprising an &agr;-pyrone compound (hereinafter, referred to as the Pyrone Compound) shown by formula:
as an active ingredient, and the composition has an extremely high knock-down activity against harmful arthropods.
DISCLOSURE OF THE INVENTION
Examples of the arthropods against which the arthropod-controlling composition of the present invention exhibits a controlling effect include the following harmful insects, acarina, Diplopoda, Chilopoda and Isopoda:
Hemiptera:
Delphacidae (planthoppers) such as
Laodelphax striatellus
(small brown planthopper),
Nilaparvata lugens
(brown planthopper) and
Sogatella furcifera
(white-backed rice planthopper); Deltocephalidae (leafhoppers) such as
Nephotettix cincticeps
(green rice leafhopper),
Recilia dorsalis
(zig-zag rice leaf hopper) and
Nephotettix virescens
(green rice leafhopper), Aphididae (aphids) such as cotton aphid (
Aphis gossypii
); stink bugs; Aleyrodidae (whiteflies) such as
Bemisia argentifolii
; scales; Tingidae (lace bugs); Psyllidae (suckers) and so on.
Lepidoptera:
Pyralidae 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),
Mamestra brassicae
(cabbage armyworm), Agrotis spp. (e.g.
Agrotis segetum
(turnip cutworm),
Agrotis ipsilon
(black cutworm)), Helicoverpa spp., Heliothis spp. and Plusiinae; Pieridae such as
Pieris rapae crucivora
(common cabbageworm); Tortricidae such as Adoxophyes spp. (e.g.
Adoxophyes orana fasciata
); Carposinidae such as
Carposina niponensis
(peach fruit moth); Lyonetiidae; Lymantriidae; Plutellidae such as
Plutella xylostella
(diamondback moth); Hesperiidae such as
Parnara guttata
(rice skipper); Tineidae such as
Tinea pellionella
(casemaking clothes moth) and
Tineola bisselliella
(webbing clothes moth) and so on.
Diptera:
Culicidae (mosquitoes) such as Culex spp. (e.g.
Culex pipiens pallens
(common mosquito),
Culex tritaeniorhynchus
), Aedes spp. (e.g.
Aedes aegypti
(yellow fever mosquito),
Aedes alhopictus
) and Anopheles spp. (e.g.
Anopheles sinensis
); Chironomidae (midges); Muscidae such as
Musca domestica
(housefly),
Muscina stabulans
(false stablefly) and
Fannia canicularis
(little housefly); Calliphoridae; Sarcophagidae; Anthomyiidae such as
Delia platura
(seedcorn maggot) and
Delia antiqua
(onion maggot); Tephritidae (fluit flies); Drosophilidae; Psychodidae (moth flies); Tabanidae; Simuhidae (black flies); Stomoxyidae; Phoridae; Ceratopogonidae (biting midges) and so on.
Coleoptera (Beetles):
Scarabaeidae (scarabs) such as
Anomala cuprea
(cupreous chafer) and
Anomala rufocuprea
(soybean beetle); Curculionidae (weevils) such as
Sitophilus zeamais
(maize weevil),
Lissorhoptrus oryzophilus
(ricewater weevil), ball weevil and
Callosobruchus chinensis
(adzuki bean weevil); Dermestidae such as
Authrenus verbasci
(varied carpet beetle) and
Attagenus unicolor japonicus
(black carpet beetle); Tenebrionidae (darkling beetles) such as
Tenebrio molitor
(yellow mealworm) and
Triboium castaneum
(red flour beetle); Chrysomelidae (leaf beetles) such as
Oulema oryzae
(rice leaf beetle),
Phyllotreta striolata
(striped flea beetle) and
Aulacophora femoralis
(cucurbit leaf beetle); Corn rootworms such as
Diabrotica virgifera
(western corn rootworm) and
Diabrotica undecimpunctata howardi
(southern corn rootworm); Anobiidae; Coccinellidae (ladybirds) such as Epilachna spp. (e.g.
Epilachna vigintioctopunctata
(twenty-eight-spotted ladybird)); Lyctidae (powderpost beetles); Bostrychidae (false powderpost beetles); Cerambycidae; Staphylinidae such as
Paederus fuscipes
(robe beetle) and so on.
Dictyoptera:
Blattella germanica
(German cockroach);
Periplaneta fuliginosa
(smokybrown cockroach);
Periplaneta americana
(American cockroach);
Periplaneta brunnea
(brown cockroach);
Blatta orientalis
(oriental cockroach) and so on;
Thysanoptera (Thrips):
Thrips palmi
, western flower thrips,
Thrips hawaiiensis
(flower thrips) and so on.
Hymenoptera:
Formicidae (ants) such as
Formica japonica
, field ant (
Lasius fuliginosus
), little red ant (
Monomorium pharaonis
), little ant (
Monomorium nipponensis
) and pavement ant (
Teramorium caespitum
); Vespidae (hornets); Polistes spp. (long-legged wasps); Bethylidae; Tenthredinidae (sawflies) such as
Athalis rosae ruficornis
(cabbage sawfly) and so on.
Orthoptera:
Gryllotalpidae (mole crickets); Acrididae (grasshoppers) and so on.
Siphonaptera Pests (Fleas):
Ctenocephalides canis
(dog flea);
Ctenocephalides felis
(cat flea);
Pulex irritans
and so on.
Anoplura (Lice):
Pediculus corporis; Pediculus humanus
(body louse);
Pthirus pubis
(crab louse) and so on.
Isoptera:
Reticulitermes speratus; Coptotermes formosanus
and so on.
Tetranychidae (Spider Mites):
Tetranychus cinnabarinus
(carmine spider mite);
Tetranychus urticae
(two-spotted spider mite);
Tetranychus kanzawai
(Kanzawa spider mite);
Panonychus citri
(citrus red mite);
Panonychus ulmi
(European red mite) and so on.
Ixodidae:
Boophilus microplus; Haemaphysalis longiconis
and so on
House-Dust Mites:
Acaridae such as
Tyrophagus putrescentiae
(copra mite) and
Aleuroglyphus ovatus
(brown legged grain mite); Dermanyssidae such as
Dermatophagoides farinae
(American house dust mite) and
Dermatophagoides pteronyssinus
; Glycyphagidae such as
Glycyphagus privatus, Glycyphagus domesticus
and
Glycyphagus destructor
; Cheyletidae such as
Chelacaropsis malaccensis
and
Cheyletus fortis
; Tarsonemidae; Chortoglyphus spp.; Haplochthonius spp. and so on.
Diplopoda (Milpedes):
Chilognatha such as Oxydus spp. and so on.
Chilopoda (Centipedes):
Scolopendra suhspinipes mutilans
, red centipede and so on.
Isopoda:
Oniscoidea (pill bugs) such as Porcellio spp. (e.g.
Porcellio scaber
), Porcellionides spp. and Armadillidium spp. (e.g.
Armadillium vulgare
) and so on.
The Pyrone Compound can be prepared according to the procedure below:
Preparation of the Pyrone Compound
Ten grams (10.0 g, 79.3 mmol) of 4-hydroxy-6-methyl-2-pyrone were suspended in 100 ml of toluene at room temperature. To the suspension, 1.22 g (10.0 mmol) of N,N-dimethylaminopyridine, 10.0 g (86.1 mmol) of isocaproic acid and 18.5 g (89.7 mmol) of dicyclohexylcarbodiimide were added subsequently. The mixed solution was stirred for one hour at room temperature, and then heated to 70° C. and stirred for 20 hours under heating. After the mixed solution was allowed to stand at room temperature, the precipitated insoluble dicyclohexylurea was filtered off, and washed with 1N hydrochloric acid once and 10% (by weight) brine twice. The organic layer collected from the filtrate was dried over anhydrous magnesium sulfate and evaporated under reduced pressure to give a crude oily product.
The oily product was su
Fujinami Michihiko
Kubota Shunichi
Pak John
Sughrue & Mion, PLLC
Sumitomo Chemical Company Limited
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