JP5093429B2 - 動物用外部寄生性害虫防除剤及びその使用方法 - Google Patents
動物用外部寄生性害虫防除剤及びその使用方法 Download PDFInfo
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- JP5093429B2 JP5093429B2 JP2000317887A JP2000317887A JP5093429B2 JP 5093429 B2 JP5093429 B2 JP 5093429B2 JP 2000317887 A JP2000317887 A JP 2000317887A JP 2000317887 A JP2000317887 A JP 2000317887A JP 5093429 B2 JP5093429 B2 JP 5093429B2
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- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/10—Hydrazines
- C07C243/22—Hydrazines having nitrogen atoms of hydrazine groups bound to carbon atoms of six-membered aromatic rings
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- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
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- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/44—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
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- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
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- C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/63—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton
- C07C255/65—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to nitrogen atoms
- C07C255/66—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to nitrogen atoms having cyano groups and nitrogen atoms being part of hydrazine or hydrazone groups bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
- C07C281/08—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones
- C07C281/14—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones the carbon atom being further bound to a carbon atom of a six-membered aromatic ring
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- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
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- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C337/06—Compounds containing any of the groups, e.g. thiosemicarbazides
- C07C337/08—Compounds containing any of the groups, e.g. thiosemicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. thiosemicarbazones
Description
【発明の属する技術分野】
本発明はヒドラジン誘導体を有効成分とする新規な動物用外部寄生性害虫防除剤及びその使用方法に関するものである。
【0002】
【従来技術】
本発明の動物用外部寄生性害虫防除剤の有効成分である一般式(I) で表されるヒドラジン誘導体は特開平5−4958号公報、同5−17428号公報、同5−32603号公報及び同5−262712号公報等に記載の公知の化合物であり、農園芸用殺虫剤としてコナガ、コブノメイガ等の鱗翅目害虫、チャノミドリヒメヨコバイ、ナシグンバイ等の半翅目害虫、ニジュウヤホシテントウ、コクゾウムシ等の甲虫目害虫、ウリミバエ、イエバエ、チカイエカ等の双翅目害虫、ミナミネグサレセンチュウ、ネコブセンチュウ等のハリセンチュウ目害虫等に殺虫作用があることが記載されている。しかし、動物の外部寄生性害虫、例えばノミ目害虫、シラミ目害虫、ダニ目害虫等に対して殺虫効果を有することは記載も示唆もされていない。
【0003】
【発明が解決しようとする課題】
従来から家畜やペット等の飼育動物に有害な外部寄生性害虫を防除する薬剤は種々提案されている。しかし、少量の薬剤処理で有効に外部寄生性害虫を防除する新規なな薬剤の創出が望まれている。
本発明者等は家畜やペット等の動物の外部寄生性害虫に対して低薬量で顕著な防除効果を有する新規な外部寄生性害虫防除剤を創出すべく鋭意研究を重ねた結果、前記先行技術に記載のヒドラジン誘導体の中で一部の化合物が動物の外部寄生性害虫に対して顕著な防除効果を有することを見いだし、本発明を完成させたものである。
【0004】
【課題を解決するための手段】
本発明は一般式(I)
【化10】
〔式中、Aは
【化11】
(式中、R4 は水素原子又はC1-6アルキル基を示し、Xは同一又は異なっても良く、水素原子、ハロゲン原子、C1-6アルキル基又はハロC1-6アルキル基から選択される1〜5個の置換基を示す。)、
【0005】
【化12】
(式中、R4 及びXは前記に同じくし、R5 は水素原子、C1-6アルキルカルボニル基又は同一若しくは異なっても良いC1-6アルキル基から選択される1〜2個の置換基を有しても良いフェニルカルボニル基を示す。)、
【化13】
(式中、R4 及びXは前記に同じ。)
又は
【0006】
【化14】
(式中、R4 及びXは前記に同じ。)
を示し、R1 は水素原子又はC1-6アルキル基を示し、R2 及びR3 は同一又は異なっても良く水素原子、水酸基、C1-6アルキル基、C1-6アルコキシ基、C1-6アルキルカルボニル基又はフェニルカルボニル基を示し、Yは同一又は異なっても良く、水素原子、ハロゲン原子、ニトロ基又はシアノ基から選択される1〜5個の置換基を示し、Zはハロゲン原子、シアノ基、C1-6アルキル基、ハロC1-6アルキル基、C1-6アルコキシ基、ハロC1-6アルコキシ基、ハロC1-6アルキルチオ基、ハロC1-6アルキルスルフィニル基又はハロC1-6アルキルスルホニル基を示し、Wは酸素原子又は硫黄原子を示す。〕
で表されるヒドラジン誘導体を有効成分として含有する動物用外部寄生性害虫防除剤及びその使用方法に関するものである。
【0007】
本発明の一般式(I) の定義で「ハロゲン原子」とは塩素原子、臭素原子、ヨウ素原子、フッ素原子を示し、「C1-6アルキル」とは炭素原子数1〜6の直鎖状又は分枝状のアルキル基を示し、「ハロC1-6アルキル」とは、同一又は異なっても良い1以上のハロゲン原子で置換された炭素原子数1〜6のアルキル基を示す。
本発明の動物用外部寄生性害虫防除剤の有効成分である一般式(I) で表されるヒドラジン誘導体は特開平5−4958号公報、同5−17428号公報、同5−32603号公報及び同5−262712号公報等に記載の製造方法により製造することができる。
以下に本発明の動物用外部寄生性害虫防除剤の有効成分である一般式(I) で表されるヒドラジン誘導体の代表的な化合物を第1表乃至第4表に例示するが、本発明はこれらに限定されるものではない。尚、表中のPhはフェニル記を示す。
【0008】
一般式(I-1)
【化15】
【0009】
【0010】
【0011】
【0012】
【0013】
【0014】
一般式(I-2)
【化16】
【0015】
【0016】
【0017】
注:表中、Phはあるのはフェニル基を示す。
化合物106及び107はジアステレオマ−であり、Rf値では106が
107より高い。
【0018】
一般式(I-3)
【化17】
【0019】
【0020】
【0021】
一般式(I-4)
【化18】
【0022】
【0023】
第1表乃至第4表中で物性が粘稠物又はガラス状の 1H−NMRデ−タを第5表に示す。
【0024】
【0025】
本発明の動物用外部寄生性害虫防除剤は、牛、馬、羊等の家畜、犬、猫等のペットの他、マウス、ラット、ハムスター、リス等のげっ歯目動物、ウサギ目動物、フェレット等の食肉目動物、アヒル、ニワトリ、ハト等の鳥類に対して使用でき、動物の外部寄生虫としては、例えばネコノミ(Ctenocephalides felis) 、イヌノミ(Ctenocephalides canis) 、ケオプスネズミノミ(Xenopsylla cheopis)等のノミ目害虫、フタトゲチマダニ(Haemaphyxalis longicornis) 、オウシマダニ(Boophilus microplus) 等のダニ目害虫、ウシジラミ(Haematopinus eurysternus)、ヒツジジラミ(Damalinia ovis)等のシラミ目害虫等の外部寄生性害虫を例示することができる。
【0026】
本発明の一般式(I) で表されるヒドラジン誘導体を有効成分とする動物用外部寄生性害虫防除剤を効率的に使用するには、一般的に通常使用される製剤処方に従って適当な固体担体及び/又は液体担体等及び必要に応じて補助剤等と共に適当な割合に配合して溶解、懸濁、混合、含浸、吸着若しくは付着させ、使用目的に応じて適当な剤形、例えば液剤、乳化剤、クリーム、軟膏、懸濁剤、エアゾール剤に調製して使用すれば良い。
【0027】
本発明で使用する固体担体又は液体担体としては、通常動物用薬剤に使用される担体を使用すれば良く、対象動物への処理のし易さから液体担体を使用するのが良く、液体担体としては、例えばメチルアルコール、エチルアルコール、イソプロピルアルコール、ターシャリーブチルアルコール、ベンジルアルコール等のアルコール類、炭酸プロピレン、N−メチル−2−ピロリドン、水等を例示することができる。
本発明の防除剤は必要の応じて補助剤を使用することができ、補助剤として界面活性剤、酸化防止剤、乳化剤等を使用することができ、例えばポリオキシエチレンアルキルアリールエーテル、ポリオキシエチレンソルビタンモノラウレート、アルキルアリルソルビタンモノラウレート、アルキルベンゼンスルホン酸塩、アルキルナフタレンスルホン酸、リグニンスルホン酸塩高級アルコール硫酸エステル塩、グリコールモノアルキルエーテル、グリコール類等の界面活性剤、モノオイレン酸ソルビタン、モノラウリン酸ソルビタン、カプリル酸モノグリセライド、カプリン酸モノグリセライド、イソステアリン酸モノグリセライド、モノカプリル酸プロピレングリコール等の乳化剤、BHA、BHT等の酸化防止剤を例示することができる。
本発明の防除剤は、防除剤100重量部中に有効成分として0.01〜80.0重量部の範囲で配合することができる。
【0028】
本発明の動物用外部寄生性害虫防除剤は、通常、対象動物体の肩甲背部の皮膚等に液状の薬剤を滴下することにより、外部寄生性害虫を防除するスポットオン処理、対象動物体の背中線に沿って液状の薬剤を処理し、処理された薬剤が体表面に拡散することにより、外部寄生性害虫を防除するポアオン処理等の局所処理法の他に、首輪等に薬剤を担持させ、薬剤を放出する処理法、直接体表面に液体又は軟膏の薬剤を塗布する処理法、スプレー等で液体のエアゾール薬剤を処理する方法等があり、その施用量は、対象動物の体重1kg当たり、有効成分化合物として、通常約0.1〜500mg、本発明防除剤として、通常約0.01〜20mlの範囲から適宜選択して処理すれば良い。
本発明の動物用外部寄生性害虫防除剤は、必要の応じて他の活性成分を併用することができ、例えばペルメトリン、フェノトリン、アレスリン、ピレトリン、プラレトリン、シフェノトリン、シフルトリン、フェンバレレート、フェンプロパトリン、トランスフルスリン等のピレスロイド系化合物、ジクロルボス、テトラクロロビンホス、フェンチオン、クロルピリホス、ダイアジノン等の有機リン系化合物、フィプロニル等のN−フェニルピラゾール系化合物、プロポキスル、カルバリル、メトキサジアゾン、フェノカルブ等のカーバメート系化合物、ネオニコチノイド系化合物等を例示することができる。
【0029】
【実施例】
実施例1.
第1表乃至第4表記載の化合物 5部
ヘキシレングリコール 50部
イソプロパノール 45部
以上を均一に混合、溶解して液剤を得た。
実施例2.
第1表乃至第4表記載の化合物 10部
ポリオキシエチレンスチリルフェニルエーテル 10部
シクロヘキサノン 80部
以上を均一に混合、溶解して乳化剤を得た。
【0030】
試験例1.
化合物44又は96を10重量部それぞれをジエチレングリコールモノエチルエーテル90重量部に混合、溶解させてスポットオン薬剤を得た。薬剤投与前日にネコノミ成虫30頭をネコに寄生させ、、ネコの頸部にエリザベスカラーを装着した。薬剤0.4mlをネコ(生体重3.2kg)の肩甲骨背部の皮膚に塗布した。薬剤処理1日後及び3日後にノミ取り櫛を用いて寄生ノミ数を調査し、寄生数調査後は全ネコノミをネコに再寄生させた。ブランクとして、無処理のネコに同様に寄生させた場合のネコノミ寄生数を調査し、下記の式により防除率を算出し、下記基準により判定を行った。
【0031】
本発明の化合物44及び96を有効成分とする外部寄生性害虫防除剤は両薬剤ともAの判定結果であった。
【0032】
【発明の効果】
本発明の動物用外部寄生性害虫防除剤は、家畜やペット等を加害する、ノミ、シラミ、ダニ等の寄生性害虫に対して顕著な防除効果を奏するものである。
Claims (2)
- 一般式(I-1)
で表されるヒドラジン誘導体を有効成分として含有することを特徴とする動物用外部寄生性害虫防除剤。 - 請求項1記載の動物用外部寄生性害虫防除剤の有効量を動物(但し、ヒトを除く。)の体表面に処理することを特徴とする動物用外部寄生性害虫防除剤の使用方法。
Priority Applications (21)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000317887A JP5093429B2 (ja) | 2000-10-18 | 2000-10-18 | 動物用外部寄生性害虫防除剤及びその使用方法 |
DK01974879T DK1334661T3 (da) | 2000-10-18 | 2001-10-16 | Midler til bekæmpelse af ektoparasitiske skadevoldende insekter på dyr, samt anvendelse heraf |
PT01974879T PT1334661E (pt) | 2000-10-18 | 2001-10-16 | Controladores de pragas de insectos ectoparasitas para animais e sua utilização |
CA002426275A CA2426275C (en) | 2000-10-18 | 2001-10-16 | Ectoparasitic insect pest controllers for animals and their usage |
NZ525191A NZ525191A (en) | 2000-10-18 | 2001-10-16 | Ectoparasitic insect pest controllers for animals and their usage |
DE122007000047C DE122007000047I2 (de) | 2000-10-18 | 2001-10-16 | Mittel zur Bekämpfung von Ektoparasitischen Schadinsekten und ihre Verwendung |
AT01974879T ATE349891T1 (de) | 2000-10-18 | 2001-10-16 | Mittel zur bekämpfung von ektoparasitischen schadinsekten und ihre verwendung |
AU2001294269A AU2001294269B2 (en) | 2000-10-18 | 2001-10-16 | Ectoparasitic insect pest controllers for animals and their usage |
CN018176283A CN1216533C (zh) | 2000-10-18 | 2001-10-16 | 动物用外寄生性害虫防治剂及其用法 |
DE60125812T DE60125812T2 (de) | 2000-10-18 | 2001-10-16 | Mittel zur Bekämpfung von Ektoparasitischen Schadinsekten und ihre Verwendung |
BRPI0114783A BRPI0114783B1 (pt) | 2000-10-18 | 2001-10-16 | controlador de pragas de insetos ectoparasitários para animais |
DE200712000048 DE122007000048I1 (de) | 2000-10-18 | 2001-10-16 | Mittel zur Bek{mpfung von Ektoparasitischen Schadeinsekten und ihre Verwendung |
ES01974879T ES2276832T3 (es) | 2000-10-18 | 2001-10-16 | Controladores de peste de insecto ectoparasito en animales y su utilizacion. |
PCT/JP2001/009076 WO2002032226A1 (fr) | 2000-10-18 | 2001-10-16 | Antiparasitaires pour animaux permettant de lutter contre des insectes ectoparasites et utilisation de ces antiparasitaires |
AU9426901A AU9426901A (en) | 2000-10-18 | 2001-10-16 | Ectoparasitic insect pest controllers for animals and their usage |
KR10-2003-7005324A KR100527653B1 (ko) | 2000-10-18 | 2001-10-16 | 동물용 외부기생성 해충 방제제 및 이의 사용 방법 |
US10/399,327 US6903237B2 (en) | 2000-10-18 | 2001-10-16 | Ectoparasitic insect pest controllers for animals and their usage |
EP01974879A EP1334661B1 (en) | 2000-10-18 | 2001-10-16 | Ectoparasitic insect pest controllers for animals and their usage |
MXPA03003294A MXPA03003294A (es) | 2000-10-18 | 2001-10-16 | Reguladores de plagas de insectos ectoparasitarios en animales y su uso. |
ZA200302735A ZA200302735B (en) | 2000-10-18 | 2003-04-08 | Ectoparasitic insect pest controllers for animals and their usage. |
CY20071100116T CY1105964T1 (el) | 2000-10-18 | 2007-01-29 | Μεσα καταπολεμησης εκτοπαρασιτικων εντομων για ζωα και η χρηση τους |
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JP2000317887A JP5093429B2 (ja) | 2000-10-18 | 2000-10-18 | 動物用外部寄生性害虫防除剤及びその使用方法 |
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JP5093429B2 true JP5093429B2 (ja) | 2012-12-12 |
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JP2000317887A Expired - Lifetime JP5093429B2 (ja) | 2000-10-18 | 2000-10-18 | 動物用外部寄生性害虫防除剤及びその使用方法 |
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US (1) | US6903237B2 (ja) |
EP (1) | EP1334661B1 (ja) |
JP (1) | JP5093429B2 (ja) |
KR (1) | KR100527653B1 (ja) |
CN (1) | CN1216533C (ja) |
AT (1) | ATE349891T1 (ja) |
AU (2) | AU9426901A (ja) |
BR (1) | BRPI0114783B1 (ja) |
CA (1) | CA2426275C (ja) |
CY (1) | CY1105964T1 (ja) |
DE (3) | DE60125812T2 (ja) |
DK (1) | DK1334661T3 (ja) |
ES (1) | ES2276832T3 (ja) |
MX (1) | MXPA03003294A (ja) |
NZ (1) | NZ525191A (ja) |
PT (1) | PT1334661E (ja) |
WO (1) | WO2002032226A1 (ja) |
ZA (1) | ZA200302735B (ja) |
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CN101828054B (zh) * | 2007-10-25 | 2014-05-07 | 株式会社小松制作所 | 作业车辆及作业车辆的控制方法 |
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CZ303846B6 (cs) * | 1999-03-12 | 2013-05-29 | Basf Aktiengesellschaft | Synergická insekticidní kompozice |
US7906128B2 (en) * | 2002-10-21 | 2011-03-15 | Wyeth Llc | Use of neuronal sodium channel antagonists for the control of ectoparasites in homeothermic animals |
WO2005046656A2 (en) * | 2003-11-04 | 2005-05-26 | Akzo Nobel N.V. | Use of 5 - chloro-1- (2, 6 - dichloro - 4 - trifluoromethylphenyl) - 4 - (4, 5 - dicyano - 1h - imidazol - 2yl) -3 - methyl - 1h - pyrazole in systemic control of acarid infestation on animals |
ATE411799T1 (de) * | 2003-11-04 | 2008-11-15 | Intervet Int Bv | Ectoparasitische formulierungen von spinosyns und azol-pestiziden |
US7371885B2 (en) * | 2003-11-14 | 2008-05-13 | Basf Aktiengesellschaft | Cis-trans isomerisation of semicarbazone compounds |
JP4745651B2 (ja) * | 2003-12-03 | 2011-08-10 | 石原産業株式会社 | 有害生物防除用組成物及び有害生物の防除方法 |
KR100595446B1 (ko) * | 2004-01-19 | 2006-07-03 | 삼성전자주식회사 | 디스플레이장치 |
EP1734939A4 (en) * | 2004-03-05 | 2010-06-30 | Univ California | PEST CONTROL COMPOUNDS AND METHODS OF USE |
US20080076805A1 (en) * | 2004-10-07 | 2008-03-27 | Lin Linus S | Acyclic Hydrazides as Cannabinoid Receptor Modulators |
PE20060785A1 (es) | 2004-10-08 | 2006-09-19 | Wyeth Corp | Composiciones de amitraz |
JP2006282618A (ja) * | 2005-04-01 | 2006-10-19 | Nippon Nohyaku Co Ltd | 農園芸用毒餌剤 |
US20060288955A1 (en) * | 2005-05-24 | 2006-12-28 | Wyeth | Device and method for controlling insects |
TWI368505B (en) * | 2005-05-24 | 2012-07-21 | Wyeth Corp | Versatile high load concentrate compositions for control of ecto-parasites |
US20060293260A1 (en) * | 2005-05-24 | 2006-12-28 | Wyeth | Useful high load concentrate compositions for control of ecto-and endo-parasites |
CN103342666A (zh) * | 2013-07-18 | 2013-10-09 | 桂林理工大学 | 3-乙氧基水杨醛缩碳酰肼双希夫碱的合成方法 |
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DE3041814A1 (de) * | 1980-11-06 | 1982-06-03 | Bayer Ag, 5090 Leverkusen | Formulierung zur bekaempfung von tierischen ektoparasiten, insbesondere insekten und acarinen |
ES2089056T3 (es) * | 1990-06-16 | 1996-10-01 | Nihon Nohyaku Co Ltd | Derivados de hidrazincarboxamida, un procedimiento para la produccion de los mismos, y usos de los mismos. |
WO1992006076A1 (en) * | 1990-10-05 | 1992-04-16 | E.I. Du Pont De Nemours And Company | Semicarbazone arthropodicides |
JP2879174B2 (ja) * | 1990-11-17 | 1999-04-05 | 日本農薬株式会社 | ヒドラゾン誘導体及びその製造方法、その用途並びにその使用方法 |
JP2879175B2 (ja) * | 1990-11-30 | 1999-04-05 | 日本農薬株式会社 | ヒドラジン誘導体並びにその製造方法、用途及び使用方法 |
JP3248003B2 (ja) * | 1992-05-19 | 2002-01-21 | 日本農薬株式会社 | ヒドラジン誘導体類及び農園芸用殺虫剤 |
ZA949293B (en) | 1993-12-08 | 1995-08-17 | Nihon Nohyaku Co Ltd | Hydrazine derivatives and uses thereof |
MY138864A (en) | 1999-07-05 | 2009-08-28 | Nihon Nohyaku Co Ltd | Ant controllers and method for application thereof |
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Also Published As
Publication number | Publication date |
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DE60125812T2 (de) | 2007-06-14 |
US6903237B2 (en) | 2005-06-07 |
CN1216533C (zh) | 2005-08-31 |
KR20030051719A (ko) | 2003-06-25 |
ZA200302735B (en) | 2004-04-08 |
CY1105964T1 (el) | 2011-04-06 |
AU2001294269B2 (en) | 2005-01-06 |
EP1334661A4 (en) | 2004-02-04 |
CA2426275A1 (en) | 2003-04-27 |
US20030199579A1 (en) | 2003-10-23 |
ATE349891T1 (de) | 2007-01-15 |
DE122007000048I1 (de) | 2007-09-13 |
ES2276832T3 (es) | 2007-07-01 |
NZ525191A (en) | 2004-10-29 |
PT1334661E (pt) | 2007-02-28 |
BRPI0114783B1 (pt) | 2016-02-23 |
AU9426901A (en) | 2002-04-29 |
CA2426275C (en) | 2007-09-11 |
MXPA03003294A (es) | 2004-05-04 |
KR100527653B1 (ko) | 2005-11-09 |
EP1334661A1 (en) | 2003-08-13 |
CN1469708A (zh) | 2004-01-21 |
BR0114783A (pt) | 2003-12-23 |
EP1334661B1 (en) | 2007-01-03 |
DE122007000047I1 (de) | 2007-09-13 |
DK1334661T3 (da) | 2007-01-29 |
DE60125812D1 (de) | 2007-02-15 |
DE122007000047I2 (de) | 2011-01-13 |
WO2002032226A1 (fr) | 2002-04-25 |
JP2002128614A (ja) | 2002-05-09 |
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