JP4787501B2 - 害虫忌避剤組成物及び化合物 - Google Patents
害虫忌避剤組成物及び化合物 Download PDFInfo
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- JP4787501B2 JP4787501B2 JP2004560442A JP2004560442A JP4787501B2 JP 4787501 B2 JP4787501 B2 JP 4787501B2 JP 2004560442 A JP2004560442 A JP 2004560442A JP 2004560442 A JP2004560442 A JP 2004560442A JP 4787501 B2 JP4787501 B2 JP 4787501B2
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Classifications
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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
- A01N37/00—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
- A01N37/18—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
- A01N37/26—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 containing the group; Thio analogues thereof
-
- 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
- A01N37/00—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
- A01N37/18—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
- A01N37/20—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 containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
-
- A—HUMAN NECESSITIES
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Description
Rは、非分枝鎖又は分枝鎖のC1〜C15アルキル、好ましくは、分枝鎖C1〜C9アルキルであり、その際、該アルキルは、置換されていないか、又は、ハロゲン、シアノ若しくはニトロで置換されており;
R1及びR2は、非分枝鎖又は分枝鎖のC1〜C12アルキル、好ましくは、C1〜C6アルキルであり、その際、該アルキルは、置換されていないか、又は、ハロゲン、シアノ若しくはニトロで置換されており;
X及びYは、互いに独立して、1〜20個の炭素原子を有する直鎖又は分枝鎖のアルキレンブリッジ、好ましくは、1〜3個の炭素原子を有するアルキレンブリッジを形成しており、その際、該アルキレンブリッジは、置換されていないか、又は、ハロゲン、シアノ若しくはニトロで置換されている]
で表される化合物である。
皮膚に適用するためのローションの形態にある害虫駆除用組成物は、30部の表1に記載されている式(I)の化合物の内の1種類の化合物、1.5部の香料及び68.5部のイソプロパノールを混合することにより調製する。ここで、イソプロパノールはエタノールで置き換えてもよい。
ペットの毛皮に噴霧するためのエーロゾルの形態にある害虫駆除用組成物は、30部の表1に記載されている式(I)の化合物の内の1種類の化合物、1.5部の香料及び68.5部のイソプロパノールからなる活性成分溶液50%を、エーロゾル缶噴射剤ガスとしてのFrigen 11/12(ハロゲン化炭化水素)50%と配合することにより調製する。
皮膚に噴霧するためのエーロゾルの形態にある害虫駆除用組成物は、20部の式(I)の化合物の内の1種類の化合物、1部の香料及び79部のイソプロパノールからなる活性成分溶液40%を、エーロゾル缶噴射剤ガスとしてのプロパン/ブタン(比率 15:85)60%と配合することにより調製する。
害虫忌避物質を試験するためのアレーナ試験法
この方法は、コンピュータ支援によるビデオシステムを使用して、横断面がそれぞれ5cmの6個のウェルを有するタイタープレートで実施する。該タイタープレートの各ウェルの内側を円形の濾紙又は別の適切な担体物質で覆う。式(I)で表される被験物質を、メタノール又はアセトニトリル又は別の適切な溶媒に溶解させ、その際、超音波処理を行い、また、溶解性が低い物質の場合は加熱する。溶解させた被験物質を、1〜100μg/cm2の量で、4分円上の濾紙の中心又は約2.4cm2半径の円形領域上の濾紙の中心に配置する。6個のウェルの内の4つには、異なった被験物質を入れるか、又は、異なった希釈(例えば、1μg/cm2、3.2μg/cm2、5μg/cm2、10μg/cm2及び20μg/cm2)の同一の被験物質を入れる。第5番目のウェルは、標準物質としてのDEET(N,N−ジエチル−m−トルアミド)で処理する。第6番目のウェルには純粋な溶媒を入れて、対照とする。被験寄生虫(例えば、マダニ)の60〜100匹の幼虫又は25〜50匹の若虫又は10〜25匹の成虫を各濾紙に添加しする。系を板ガラスで覆い、ビデオカメラの下に置く。
この試験は、各ウェル当たり約25〜50匹の若虫を添加して、上記で記載されているようにして実施する。10mgの溶解させた被験物質を、2.4cm2半径の領域に適用する。ビデオ映像を評価することにより、式(I)の化合物がAmblyommaの若虫に対して著しい忌避作用を示すことが分かる。この忌避作用は、DEETの忌避作用に比較して著しく長い時間持続する。特に長期にわたる作用を示したのは、例えば、化合物番号1.31であり、これは、3.2μg/cm2まで希釈しても特に長期にわたる作用を示す。
この試験は、各ウェル当たり約60〜100匹の幼虫を添加して、上記で記載されているようにして実施する。10mgの溶解させた被験物質を、2.4cm2半径の領域に適用する。ビデオ映像を評価することにより、式(I)の化合物がBoophilusの幼虫に対して著しい忌避作用を示すことが分かる。この忌避作用は、DEETの忌避作用に比較して著しく長い時間持続する。特に長期にわたる作用を示したのは、例えば、化合物番号1.31であり、これは、3.2μg/cm2まで希釈しても特に長期にわたる作用を示す。
約40〜50匹の若虫を用いて、実施例Bと同様に試験を行う。ビデオ映像を評価することにより、本発明の化合物が良好な忌避作用を示すことが分かる。特に、本発明の化合物は、その殆ど完全な忌避作用に関して傑出しており、この忌避作用は、DEETの忌避作用に比較して著しく長い時間持続する。特に長期にわたる作用を示したのは、例えば、化合物番号1.31であり、これは、3.2μg/cm2まで希釈しても特に長期にわたる作用を示す。
活性成分の下記製剤を、以下の試験で使用する。
活性物質:15% N,N−ジエチル−3−メチルベンズアミド(DEET);15% エチルブチルアセチルアミノプリピオネート(EBAAP);イソプロパノール、メタクリル酸コポリマー、カルバミド、芳香物質(香料)。
活性物質:2−プロピル−ペンタン酸−ビス−(2−メトキシエチル)−アミド 4.5%;Pluronic F6(登録商標) 2.0%;水 10.0%、イソプロパノール 100.0%まで。
Claims (13)
- 害虫忌避剤組成物であって、少なくとも1種の適切な希釈剤又は拡展性添加剤と、活性成分として、式(I):
- Rが、分枝鎖C1〜C9アルキルであり、R1、R2、X及びYは、請求項1で定義されているとおりであることを特徴とする、請求項1に記載の組成物。
- 活性成分として、式(I)[式中、RはCH(C1〜C4アルキル)2であり、その際、2つのC1〜C4アルキル基は同一又は異なる長さを有する分枝鎖又は非分枝鎖であり、R1、R2、X及びYは、請求項1で定義されているとおりである]で表される化合物を含有することを特徴とする、請求項1に記載の組成物。
- 活性成分として、式(I)[式中、RはCH(C3H7−n)2であり、R1、R2、X及びYは、請求項1で定義されているとおりである]で表される化合物を含有することを特徴とする、請求項1〜3の何れか1項に記載の組成物。
- 活性成分として、式(I)[式中、X及びYは、互いに独立して、メチレン又はエチレンであり、R、R1及びR2は、請求項1で定義されているとおりである]で表される化合物を含有することを特徴とする、請求項1〜4の何れか1項に記載の組成物。
- 活性成分として、式(I)[式中、R1及びR2は、互いに独立して、メチル又はエチルであり、R、X及びYは、請求項1で定義されているとおりである]で表される化合物を含有することを特徴とする、請求項1〜5の何れか1項に記載の組成物。
- 活性成分として、化合物2−プロピル−ペンタン酸−ビス−(2−メトキシ−エチル)−アミドを含有することを特徴とする、請求項1に記載の組成物。
- アルコール溶液の形態で存在していることを特徴とする、請求項1〜7の何れか1項に記載の害虫忌避剤組成物。
- ポアオン製剤又はスポットオン製剤の形態で存在していることを特徴とする、請求項1〜8の何れか1項に記載の害虫忌避剤組成物。
- 首輪又はタグの形態で存在していることを特徴とする、請求項1〜7の何れか1項に記載の害虫忌避剤組成物。
- 害虫忌避剤組成物を製造するための、請求項1〜7の何れか1項に記載の式(I)の化合物の使用。
- 害虫が望まれない場所又は材料物質から害虫を駆除する方法であって、有効量の請求項1〜7の何れか1項に記載の式(I)の化合物を、害虫を駆除しようとする場所又は材料物質に適用することを特徴とする、前記方法。
- 害虫を忌避するための組成物を調製する方法であって、請求項1〜7の何れか1項に記載の式(I)の化合物を適切な添加剤と混合することを特徴とする、前記方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02028328.9 | 2002-12-17 | ||
EP02028328A EP1431277A1 (de) | 2002-12-17 | 2002-12-17 | Amidverbindungen und ihre Verwendung zur Abwehr von Ungeziefer |
PCT/EP2003/014336 WO2004054964A1 (en) | 2002-12-17 | 2003-12-16 | Vermin-repellant compositions and compounds |
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JP2010235145A Division JP5284331B2 (ja) | 2002-12-17 | 2010-10-20 | 害虫忌避剤組成物及び化合物 |
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JP2006509820A JP2006509820A (ja) | 2006-03-23 |
JP2006509820A5 JP2006509820A5 (ja) | 2007-04-12 |
JP4787501B2 true JP4787501B2 (ja) | 2011-10-05 |
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JP2010235145A Expired - Lifetime JP5284331B2 (ja) | 2002-12-17 | 2010-10-20 | 害虫忌避剤組成物及び化合物 |
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US (1) | US7749526B2 (ja) |
EP (2) | EP1431277A1 (ja) |
JP (2) | JP4787501B2 (ja) |
CN (1) | CN1300099C (ja) |
AT (1) | ATE486843T1 (ja) |
AU (1) | AU2003292248B2 (ja) |
BR (1) | BR0317337B1 (ja) |
CA (1) | CA2506818C (ja) |
DE (1) | DE60334840D1 (ja) |
DK (1) | DK1575902T3 (ja) |
ES (1) | ES2355501T3 (ja) |
MX (1) | MXPA05006516A (ja) |
WO (1) | WO2004054964A1 (ja) |
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US9913477B2 (en) | 2015-11-16 | 2018-03-13 | Alexander O Johnson | Small animal repellent comprising an aromatic salt |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US3515754A (en) * | 1964-08-26 | 1970-06-02 | Us Agriculture | N,n-disubstituted amides |
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Publication number | Priority date | Publication date | Assignee | Title |
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US3519661A (en) * | 1964-08-26 | 1970-07-07 | Us Agriculture | N,n-disubstituted amides |
US3309333A (en) * | 1964-08-26 | 1967-03-14 | Robert R Mod | N, n-disubstituted amides and their use as plasticizers in vinyl chloride resins |
US3584030A (en) * | 1966-12-16 | 1971-06-08 | Us Agriculture | Ethyl 2,2-dimethyl-3(di(2-methoxyethyl) amino)carbonylcyclobutaneacetate |
US3538123A (en) * | 1969-04-10 | 1970-11-03 | Us Agriculture | N,n-bis(2 - ethoxyethyl)epoxystearamide as a primary plasticizer for vinyl-type resins |
US3712926A (en) * | 1969-04-25 | 1973-01-23 | Basf Ag | Production of n-polyalkoxymethylamides |
JPS4842279B1 (ja) * | 1970-10-16 | 1973-12-11 | ||
SU1525148A1 (ru) * | 1988-03-02 | 1989-11-30 | Ленинградский Институт Киноинженеров | N,N @ -Бис-изопропоксиметил-амид уксусной кислоты в качестве дубител эмульсионных желатиновых светочувствительных слоев |
JPH0625684A (ja) * | 1991-12-26 | 1994-02-01 | Ethyl Japan Kk | 潤滑油用摩擦調整剤およびそれを含む潤滑油組成物 |
CA2130375C (en) * | 1993-10-01 | 2004-08-17 | Lynn Sue James | Insecticide and insect repellant compositions |
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2002
- 2002-12-17 EP EP02028328A patent/EP1431277A1/de not_active Withdrawn
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2003
- 2003-12-16 US US10/537,871 patent/US7749526B2/en active Active
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Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3515754A (en) * | 1964-08-26 | 1970-06-02 | Us Agriculture | N,n-disubstituted amides |
Also Published As
Publication number | Publication date |
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BR0317337B1 (pt) | 2013-10-22 |
EP1431277A1 (de) | 2004-06-23 |
JP2006509820A (ja) | 2006-03-23 |
CA2506818A1 (en) | 2004-07-01 |
JP5284331B2 (ja) | 2013-09-11 |
AU2003292248A1 (en) | 2004-07-09 |
CN1300099C (zh) | 2007-02-14 |
CN1723191A (zh) | 2006-01-18 |
DE60334840D1 (de) | 2010-12-16 |
ATE486843T1 (de) | 2010-11-15 |
CA2506818C (en) | 2012-04-10 |
WO2004054964A1 (en) | 2004-07-01 |
US20060140996A1 (en) | 2006-06-29 |
US7749526B2 (en) | 2010-07-06 |
BR0317337A (pt) | 2005-11-08 |
AU2003292248B2 (en) | 2007-10-11 |
MXPA05006516A (es) | 2005-08-26 |
EP1575902A1 (en) | 2005-09-21 |
ES2355501T3 (es) | 2011-03-28 |
JP2011079832A (ja) | 2011-04-21 |
DK1575902T3 (da) | 2011-02-14 |
EP1575902B1 (en) | 2010-11-03 |
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