JPH048405B2 - - Google Patents
Info
- Publication number
- JPH048405B2 JPH048405B2 JP58184104A JP18410483A JPH048405B2 JP H048405 B2 JPH048405 B2 JP H048405B2 JP 58184104 A JP58184104 A JP 58184104A JP 18410483 A JP18410483 A JP 18410483A JP H048405 B2 JPH048405 B2 JP H048405B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- methylphenyl
- isopropyl
- pyrethroid
- carbamate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 20
- 238000003958 fumigation Methods 0.000 claims description 12
- 239000002728 pyrethroid Substances 0.000 claims description 12
- 230000000749 insecticidal effect Effects 0.000 claims description 11
- 239000002917 insecticide Substances 0.000 claims description 9
- 239000003963 antioxidant agent Substances 0.000 claims description 8
- 230000003078 antioxidant effect Effects 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 description 11
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 9
- 241000257226 Muscidae Species 0.000 description 9
- 241000607479 Yersinia pestis Species 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- 241000255925 Diptera Species 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 3
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 3
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 3
- LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 description 3
- 229940024113 allethrin Drugs 0.000 description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002316 fumigant Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000000077 insect repellent Substances 0.000 description 3
- ZIQRQYBHDFMALE-UHFFFAOYSA-N methyl-(4-methyl-2-propan-2-ylphenyl)carbamic acid Chemical compound CC(C)C1=CC(C)=CC=C1N(C)C(O)=O ZIQRQYBHDFMALE-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 241001600408 Aphis gossypii Species 0.000 description 2
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 2
- 241001414720 Cicadellidae Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 2
- 241000320508 Pentatomidae Species 0.000 description 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- YFZJZJIUKMANKN-UHFFFAOYSA-N methyl n-methyl-n-phenylcarbamate Chemical compound COC(=O)N(C)C1=CC=CC=C1 YFZJZJIUKMANKN-UHFFFAOYSA-N 0.000 description 2
- 229960005235 piperonyl butoxide Drugs 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- LNJXZKBHJZAIKQ-UHFFFAOYSA-N 1,1,1,2-tetrachloro-3-(2,3,3,3-tetrachloropropoxy)propane Chemical compound ClC(Cl)(Cl)C(Cl)COCC(Cl)C(Cl)(Cl)Cl LNJXZKBHJZAIKQ-UHFFFAOYSA-N 0.000 description 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 1
- GPNYZBKIGXGYNU-UHFFFAOYSA-N 2-tert-butyl-6-[(3-tert-butyl-5-ethyl-2-hydroxyphenyl)methyl]-4-ethylphenol Chemical compound CC(C)(C)C1=CC(CC)=CC(CC=2C(=C(C=C(CC)C=2)C(C)(C)C)O)=C1O GPNYZBKIGXGYNU-UHFFFAOYSA-N 0.000 description 1
- 241001143309 Acanthoscelides obtectus Species 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- STUSTWKEFDQFFZ-UHFFFAOYSA-N Chlordimeform Chemical compound CN(C)C=NC1=CC=C(Cl)C=C1C STUSTWKEFDQFFZ-UHFFFAOYSA-N 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001466042 Fulgoromorpha Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241000406668 Loxodonta cyclotis Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000005916 Methomyl Substances 0.000 description 1
- 241001477931 Mythimna unipuncta Species 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000500441 Plutellidae Species 0.000 description 1
- WABPPBHOPMUJHV-UHFFFAOYSA-N Sesamex Chemical compound CCOCCOCCOC(C)OC1=CC=C2OCOC2=C1 WABPPBHOPMUJHV-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 240000004460 Tanacetum coccineum Species 0.000 description 1
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- -1 and pyridafenethione Chemical compound 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- XOZUGNYVDXMRKW-AATRIKPKSA-N azodicarbonamide Chemical compound NC(=O)\N=N\C(N)=O XOZUGNYVDXMRKW-AATRIKPKSA-N 0.000 description 1
- 235000019399 azodicarbonamide Nutrition 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- IRUJZVNXZWPBMU-UHFFFAOYSA-N cartap Chemical compound NC(=O)SCC(N(C)C)CSC(N)=O IRUJZVNXZWPBMU-UHFFFAOYSA-N 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 229960002483 decamethrin Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- NBTSIRSZHSMCAH-UHFFFAOYSA-N methyl-(4-methylphenyl)carbamic acid Chemical compound OC(=O)N(C)C1=CC=C(C)C=C1 NBTSIRSZHSMCAH-UHFFFAOYSA-N 0.000 description 1
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 1
- WLLGXSLBOPFWQV-OTHKPKEBSA-N molport-035-783-878 Chemical compound C([C@H]1C=C2)[C@H]2C2C1C(=O)N(CC(CC)CCCC)C2=O WLLGXSLBOPFWQV-OTHKPKEBSA-N 0.000 description 1
- GRRYSIXDUIAUGY-UHFFFAOYSA-N n-methylcarbamoyl chloride Chemical compound CNC(Cl)=O GRRYSIXDUIAUGY-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- SBNFWQZLDJGRLK-UHFFFAOYSA-N phenothrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- PWYIUEFFPNVCMW-UHFFFAOYSA-N propaphos Chemical compound CCCOP(=O)(OCCC)OC1=CC=C(SC)C=C1 PWYIUEFFPNVCMW-UHFFFAOYSA-N 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000011685 response to pyrethroid Effects 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は一般式
（式中、Ｘはメチル基、クロル原子又はブロモ
原子を表し、Ｒは水素原子又はシアノ基を表す。）
で示されるピレスロイド系化合物の１種又は２種
と、２−イソプロピル−４−メチルフエニル−Ｎ
−メチルカーバメートとを９〜２：１〜８の組成
比で含有する混合殺虫組成物に、加熱燻蒸補助剤
としての酸化防止剤を上記混合殺虫組成物１に対
し、0.01〜1.0の組成比で含有することを特徴と
する加熱燻蒸殺虫剤に関する。
アルキル置換フエニル−Ｎ−メチルカーバメー
トは農業害虫に対する殺虫剤として広く使用され
ているが、本発明のカーバメートは散布用殺虫剤
としての効果は低く実用に供し得る効力は有して
いない。
しかしながら本発明者らは、この化合物を加熱
燻蒸用として使用した時、非常に高い効力を有す
ることを見い出し、昭和47年特許を出願した。
（特願昭47−51067）
ところで一般式（）で示されるピレスロイド
系化合物は、種々の衛生害虫および農園芸害虫に
極めて優れた殺虫効果を示す一方、温血動物に対
する毒性は低く、既に家庭用、防疫用、農業用殺
虫剤として広く実用に供されている。今日まで、
これらピレスロイド剤に対する抵抗性の発達は困
難なものとされ、事実、本邦においては、実際防
除面で問題となつた例はないが、北欧のイエバエ
や、東南アジアのコナガにはピレスロイド抵抗性
系統が出現しており、生物が種の存続の場で示す
したたかさを考えれば、本邦においても抵抗性発
達の可能性を前提として対処するのが妥当と考え
られる。しかも、これらピレスロイド抵抗性発達
には、代謝系によらず神経感受性低下に基づく機
構の関与が認められ、その結果、ピレスロイド交
差抵抗性の現象が出現しており、その解決法とし
て、有機リン剤、カーバメート剤等、ピレスロイ
ドと生理作用の異なる薬剤との混用を含めた施用
面での開発が重要となつてきた。
そこで本発明者らは一般式（）のピレスロイ
ドと２−イソプロピル−４−メチルフエニル−Ｎ
−メチルカーバメート剤との混合剤を検討し、鋭
意研究を重ねた結果、一般式（）のピレスロイ
ドと２−イソプロピル−４−メチルフエニル−Ｎ
−メチルカーバメートとを９〜２：１〜８の組成
比で含有する混合殺虫組成物が、加熱燻蒸用とし
て使用された時、その相乗効果のみならず、低抗
性対策の点で極めて優れていること、更に加熱燻
蒸補助剤として酸化防止剤を上記混合殺虫組成物
１に対し0.01〜1.0の組成比で加えることによつ
て有効成分の揮散率が非常に向上するとことを見
い出し本発明を完成した。すなわち、２−イソプ
ロピル−４−メチルフエニル−Ｎ−メチルカーバ
メートとピレスロイドとの組み合わせが、特異的
に、従来の効果つまりカーバメートの致死力とピ
レスロイドの速効性を補足するだけの効果以上の
ものを示し、しかも抵抗性害虫に極めて有効であ
るという発見は、従来の散布用殺虫剤としての効
力からは全く予期しえないものである。
又、酸化防止剤の添加が、製剤貯蔵中の分解防
止に役立つだけでなく、加熱燻蒸煙の際の特にカ
ーバメート剤の分解を抑えて揮散率を向上させ、
ひいては、残効性の改善に寄与するという知見は
実用上非常に有用である。
本発明で有効成分として用いる一般式（）の
ピレスロイドは公知であり、常温で固体又は液体
である。その代表的なものをあげると次の如くで
あるが、本発明はこれらのみに限定されるもので
はない。なお、いずれのピレスロイドも酸部分に
２つの不斉炭素を、Ｒがシアノ基の場合は更に１
個の不斉炭素を有し、これらに基づく光学異性体
が存在するが、各々の異性体あるいはその混合物
も当然本発明に含まれる。
(1) 3′−フエノキシベンジル クリサンセメート
(2) 3′−フエノキシ−α′−シアノベンジル クリ
サンセメート
(3) 3′−フエノキシベンジル、２，２−ジメチル
−３−（２，２−ジクロロビニル）シクロプロ
パンカルボキシレート
(4) 3′−フエノキシ−α′−シアノベンジル２，２
−ジメチル−３−（２，２−ジクロロビニル）
シクロプロパンカルボキシレート
(5) 3′−フエノキシ−α′−シアノベンジル２，２
−ジメチル−３−（２，２−ジブロモビニル）
シクロプロパンカルボキシレート
一方、本発明で用いる２−イソプロピル−４−
メチルフエニル−Ｎ−メチルカーバメートは常温
で固体（m.p.104〜106℃）であり、カーバメート
製造の一般方法に準じて２−イソプロピル−４−
メチルフエノールとメチルイソシアネート又はメ
チルカルバミン酸クロライドとを反応させること
によつて容易に製造することができる。又、本発
明で加熱燻蒸補助剤として使用される酸化防止剤
をあげると次の如くであるがもちろんこれらのみ
に限定されるものではない。
(A) BHT（ジブチルヒドロキシトルエン）
(B) BHA（ブチルヒドロキシアニゾール）
(C) DBH（２，５−ジターシヤリブチルハイドロ
キノン）
(D) ヨシノツクス425
(E) ヨシノツクスBB｛４，4′−ブチリデン−ビス
−（６−ターシヤリブチル−３−メチルフエノ
ール）｝
これを加熱燻蒸用殺虫剤として用いる場合は前
記のピレスロイド、カーバメート剤及び酸化防止
剤混合組成物をそのまま又は適当な溶媒で溶液と
なした後、これを木粉、その他適当な基材と混合
して蚊取線香の如き剤型として用いることができ
る。更に、前記組成物を燃焼剤と混合して燃焼剤
の燃焼熱及び発煙により薬剤を発散させるいわゆ
る燻煙剤として用いる方法や、あるいは有機発泡
剤と混合封入パツクし、混合物を間接的に加熱て
燃焼を伴なうことなく有機発泡剤を熱分解させ、
該熱分解ガスの作用により薬剤を有効に燻蒸させ
る方法も可能である。また、加熱燻蒸剤として、
前記組成物を後述する電気蚊取器の如き形態に適
用することもできる。なお、前記組成物はこれに
Ｎ−オクチルビシクロヘプテンジカルボキシイミ
ド（商品名MGK−264）、Ｎ−オクチルビシクロ
ヘプテンジカルボキシイミドとアリールスルホン
酸塩との混合物（商品名MGK−5026）、オクタ
クロロジプロピルエーテル、ピペロニルブトキサ
イド、サイネピリン500、β−ブトキシ−βチオ
シアノジエチルエーテル（商品名リーセン384）、
セサメツクス等のピレスロイド用共力剤を加える
と、その殺虫効力を一層高めることができる。
また他の活性成分例えばフエニトロチオン、
DDVP、ダイアジノン、プロパホス、ピリダフ
エンチオンなどの有機リン剤、セビン、メオバー
ル、サンサイド等のカーバメート剤、カルタツ
プ、クロルフエナミジン、メソミルなどの殺虫
剤、殺ダニ剤、殺菌剤、殺線虫剤、防草剤、植物
生長調整剤、肥料その他の農薬を混合することに
よつて効果のすぐれた多目的組成物を得ることも
できる。
本発明組成物の用途として、感受性害虫はもち
ろん、有機リン剤、カーバメート剤抵抗性あるい
はkdr系各種害虫例えばハエ、蚊、ゴキブリ等の
衛生害虫をはじめ、ツマグロヨコバイ、ウンカ類
や、ニカメイチユウ、カメムシ類、ハマキ、アブ
ラムシ、カイガラムシ、ヨトウガ、マメゾウムシ
等の農業害虫、コクゾウ等の貯穀害虫、あるいは
ダニ類等の防除に極めて有用である。
次に前記組成物を加熱燻蒸用殺虫剤として用い
た場合の殺虫駆除成積を示す。
(1) 殺虫成分として3′−フエノキシ−α′−シアノ
ベンジル クリサンセメート（化合物(A)）0.15
％と２−イソプロピル−４−メチルフエニル−
Ｎ−メチルカーバメート（化合物(B)）0.15％及
びDBH0.05％を含有する蚊取線香及び対照と
してそれぞれ化合物(A)0.3％、化合物(B)0.3％、
化合物(A)0.15％と化合物(B)0.15％、アレスリン
0.3％を含む５種の蚊取線香を作り、アカイエ
カ成虫を落下仰転せしめる効果を試験した。な
お、この実験は「防虫科学」16巻（1951年）第
176頁所載の長沢、勝田等の方法によつて行な
われたものであり、この方法によつて上記線香
の相対有効度を算出したところ次の如き結果が
得られた。また、各線香について有効成分の揮
散率の測定も行なつた。
The present invention is based on the general formula (In the formula, X represents a methyl group, a chloro atom, or a bromo atom, and R represents a hydrogen atom or a cyano group.)
One or two of the pyrethroid compounds shown and 2-isopropyl-4-methylphenyl-N
- Methyl carbamate in a composition ratio of 9 to 2:1 to 8, and an antioxidant as a heat fumigation aid in a composition ratio of 0.01 to 1.0 to the above mixed insecticidal composition 1. The present invention relates to a heating fumigation insecticide characterized by containing the following: Although alkyl-substituted phenyl-N-methyl carbamates are widely used as insecticides against agricultural pests, the carbamate of the present invention has low effectiveness as a spray insecticide and does not have any practical efficacy. However, the present inventors discovered that this compound had extremely high efficacy when used for heat fumigation, and filed a patent application in 1971.
(Japanese Patent Application No. 47-51067) By the way, the pyrethroid compound represented by the general formula () has an extremely excellent insecticidal effect on various sanitary pests and agricultural and horticultural pests, but its toxicity to warm-blooded animals is low, and it has already been used for household use. It is widely used as an insecticide for epidemic prevention and agriculture. until today,
Developing resistance to these pyrethroids is said to be difficult, and in fact, there has never been a problem in terms of control in Japan, but pyrethroid-resistant strains have appeared in house flies in Northern Europe and diamondback moths in Southeast Asia. Considering the tenacity shown by living organisms to ensure the survival of their species, it is considered appropriate to take measures based on the possibility of resistance development in Japan as well. Moreover, the development of these pyrethroid resistances has been recognized to involve a mechanism based on decreased neurosensitivity, regardless of the metabolic system, and as a result, the phenomenon of pyrethroid cross-resistance has appeared, and as a solution to this, organophosphate It has become important to develop applications, including the mixed use of pyrethroids and drugs with different physiological effects, such as carbamate agents. Therefore, the present inventors proposed that the pyrethroid of the general formula () and 2-isopropyl-4-methylphenyl-N
- After considering mixtures with methyl carbamate agents and conducting intensive research, we found that pyrethroid of the general formula () and 2-isopropyl-4-methylphenyl-N
- When a mixed insecticidal composition containing methyl carbamate in a composition ratio of 9-2:1-8 is used for heat fumigation, it is extremely superior not only in its synergistic effect but also in terms of low resistance measures. The present invention was completed after discovering that the volatilization rate of the active ingredient can be greatly improved by adding an antioxidant as a heating fumigation aid at a composition ratio of 0.01 to 1.0 to 1 of the above mixed insecticidal composition. did. That is, the combination of 2-isopropyl-4-methylphenyl-N-methylcarbamate and pyrethroid specifically exhibits more than the conventional effects, that is, an effect that only supplements the lethal power of carbamate and the fast-acting effect of pyrethroid; Moreover, the discovery that it is extremely effective against resistant pests is completely unexpected from the efficacy of conventional spray insecticides. In addition, the addition of antioxidants not only helps prevent decomposition during storage of the preparation, but also suppresses the decomposition of carbamate agents during heated fumigation and improves the volatilization rate.
Furthermore, the knowledge that it contributes to improving the aftereffects is extremely useful in practice. The pyrethroid of general formula () used as an active ingredient in the present invention is known and is solid or liquid at room temperature. Typical examples thereof are as follows, but the present invention is not limited thereto. In addition, all pyrethroids have two asymmetric carbon atoms in the acid moiety, and if R is a cyano group, an additional one
Although there are optical isomers based on these asymmetric carbon atoms, each isomer or a mixture thereof is naturally included in the present invention. (1) 3'-Phenoxybenzyl chrysanthemate (2) 3'-Phenoxy-α'-cyanobenzyl chrysanthemate (3) 3'-Phenoxybenzyl, 2,2-dimethyl-3-(2 ,2-dichlorovinyl)cyclopropanecarboxylate (4) 3'-phenoxy-α'-cyanobenzyl 2,2
-dimethyl-3-(2,2-dichlorovinyl)
Cyclopropanecarboxylate (5) 3'-phenoxy-α'-cyanobenzyl 2,2
-dimethyl-3-(2,2-dibromovinyl)
Cyclopropane carboxylate On the other hand, 2-isopropyl-4- used in the present invention
Methylphenyl-N-methylcarbamate is a solid at room temperature (mp 104-106°C), and can be prepared from 2-isopropyl-4-according to the general method for carbamate production.
It can be easily produced by reacting methylphenol with methyl isocyanate or methylcarbamic acid chloride. Further, the antioxidants that can be used as heat fumigation aids in the present invention are as follows, but of course they are not limited to these. (A) BHT (dibutylhydroxytoluene) (B) BHA (butylhydroxyanisole) (C) DBH (2,5-ditertiarybutylhydroquinone) (D) Yoshinox 425 (E) Yoshinox BB {4,4'- Butylidene-bis-(6-tertiarybutyl-3-methylphenol)} When using this as an insecticide for heat fumigation, the above-mentioned mixed composition of pyrethroid, carbamate and antioxidant can be used as it is or in a solution with an appropriate solvent. After this, it can be mixed with wood flour or other suitable base material and used as a dosage form such as a mosquito coil. Furthermore, there is a method in which the composition is mixed with a combustion agent and used as a so-called smoking agent in which the chemical is released by the combustion heat and smoke generated by the combustion agent, or it is mixed with an organic foaming agent and packaged, and the mixture is heated indirectly. Pyrolyzes organic blowing agents without combustion,
A method of effectively fumigating the drug by the action of the pyrolysis gas is also possible. Also, as a heating fumigant,
The composition can also be applied to a form such as an electric mosquito repellent described below. The above composition also contains N-octylbicycloheptenedicarboximide (trade name MGK-264), a mixture of N-octylbicycloheptenedicarboximide and an arylsulfonate (tradename MGK-5026), octachloro Dipropyl ether, piperonyl butoxide, cinepirin 500, β-butoxy-βthiocyanodiethyl ether (trade name Riesen 384),
Addition of a pyrethroid synergist such as Sesamex can further enhance its insecticidal efficacy. Also other active ingredients such as fenitrothion,
Organophosphorus agents such as DDVP, diazinon, propaphos, and pyridafenethione, carbamate agents such as Sevin, Meovar, and Sancide, insecticides such as Cartap, chlorphenamidine, and methomyl, acaricides, fungicides, and nematocides. A highly effective multipurpose composition can also be obtained by mixing pesticides, herbicides, plant growth regulators, fertilizers, and other agricultural chemicals. The composition of the present invention can be used not only for sensitive insect pests, but also for various sanitary insect pests such as organic phosphorus agent, carbamate agent resistant or KDR insect pests such as flies, mosquitoes, and cockroaches, as well as leafhoppers, planthoppers, stinkbugs, stink bugs, etc. It is extremely useful for controlling agricultural pests such as leafhoppers, aphids, scale insects, armyworms, and bean weevils, grain storage pests such as black elephant, and mites. Next, the insecticidal and extermination results will be shown when the above composition is used as an insecticide for heat fumigation. (1) 3′-phenoxy-α′-cyanobenzyl chrysanthemate (compound (A)) as an insecticidal ingredient: 0.15
% and 2-isopropyl-4-methylphenyl-
Mosquito coils containing 0.15% N-methyl carbamate (compound (B)) and 0.05% DBH, and as a control 0.3% compound (A) and 0.3% compound (B), respectively.
Compound (A) 0.15% and Compound (B) 0.15%, allethrin
Five types of mosquito repellent incense containing 0.3% were made and tested for their effectiveness in making Culex mosquito adults fall and fall upside down. This experiment was published in "Insect Control Science" Volume 16 (1951).
This was carried out using the method of Nagasawa, Katsuta et al., published on page 176, and when the relative effectiveness of the above-mentioned incense sticks was calculated using this method, the following results were obtained. Furthermore, the volatilization rate of the active ingredient was also measured for each incense stick.
【表】
試験の結果、化合物(A)と化合物(B)の混合剤は顕
著な相剰効果を示し、更に酸化防止剤を加えた
本発明化合物においては、揮散率の著しい改善
によつて予期される以上の効力増強が認められ
た。
(2) 殺虫成分として3′−フエノキシベンジル ｄ
−シス，トランス−クリサンセメート（商品名
スミスリン，化合物(C)）と２−イソプロピル−
４−メチルフエニル−Ｎ−メチルカーバメート
（化合物(B)）及び酸化防止剤の混合と、対照と
して化合物(B)のかわりに３−メチルフエニル−
Ｎ−メチルカーバメート（化合物(D)）を用いた
混合剤及びアレスリンの所定薬量のアセトン溶
液を30mm×60mm×1.5mmのパルプ板に吸着させ
風乾する。このパルプ板を160℃の発熱体の上
に剰せ、加熱蒸散させる電気蚊取方式により、
イエバエ成虫を用いて効果試験を行なつた。す
なわち、25m3部屋で、イエバエ30匹を放つたス
テンレスケージを天井より50cmの高さにつる
し、４時間曝露後落下仰転したイエバエ成虫数
から薬剤の相対有効度を算出し、合わせて24時
間後の死虫率を調べたところ次の如くであつ
た。なお供試イエバエとして感受性と、実験室
レベルで幾世代にもわたつて淘太されたkdrの
両系統を用いた。[Table] As a result of the test, the mixture of Compound (A) and Compound (B) showed a remarkable synergistic effect, and the compound of the present invention in which an antioxidant was added showed a remarkable improvement in the volatilization rate, which was expected. A greater increase in efficacy than was observed was observed. (2) 3′-phenoxybenzyl d as an insecticidal ingredient
-cis,trans-chrysansemate (trade name: Sumitrin, compound (C)) and 2-isopropyl-
Mixing of 4-methylphenyl-N-methylcarbamate (compound (B)) and antioxidant, and as a control, 3-methylphenyl-N-methylcarbamate (compound (B)) instead of compound (B).
An acetone solution of a mixture using N-methyl carbamate (compound (D)) and allethrin in a predetermined amount is adsorbed onto a pulp board of 30 mm x 60 mm x 1.5 mm and air-dried. This pulp board is placed on top of a heating element heated to 160°C, and an electric mosquito repellent method is used to evaporate heat.
Efficacy tests were conducted using adult house flies. In other words, in three 25m rooms, stainless steel cages containing 30 houseflies were suspended at a height of 50cm from the ceiling, and the relative effectiveness of the drug was calculated from the number of adult houseflies that fell and turned upside down after 4 hours of exposure. When we investigated the mortality rate afterwards, it was as follows. As test house flies, we used both susceptible and kdr strains that had been culled over many generations at the laboratory level.
【表】
相対有効度はアレスリンの感受性イエバエに対
する効力を100として示す。
試験の結果、本発明組成物（試料２〜４）は
感受性イエバエに対しては顕著な相剰効果を示
す一方、kdr系イエバエに対しては従来のピレ
スロイド単剤あるいは他のカーバメート剤との
混合剤に比べて極めて有効であることが認めら
れた。
(3) 殺虫成分として3′−フエノキシベンジル
２，２−ジメチル−３−（２，２−ジクロロビ
ニル）シクロプロパンカルボキシレート（バー
メスリン，化合物(E)）と２−イソプロピル−４
−メチルフエニル−Ｎ−メチルカーバメート
（化合物(B)）を所定量含有する燻蒸剤を調製し、
ビニールハウス内でのきゆうりのワタアブラム
シについて下記方法で試験を行なつたた。
耕種既要 きゆうり
品 種 久留米Ｈ型 試験時草丈1.3〜1.5
ｍ
区制．面積 ハウス容積 400m2
調査月日．方法 ハウスを９等分し高さ1.0〜
1.5ｍの１ケ所、１葉を選定し、寄生するワタア
ブラムシの寄生数を調べた。燻蒸後24時間後に生
存虫数を調査した。[Table] Relative efficacy is expressed with the efficacy of allethrin against susceptible house flies as 100. As a result of the test, the compositions of the present invention (samples 2 to 4) showed a remarkable synergistic effect against susceptible house flies, while the compositions of the present invention (samples 2 to 4) showed significant synergistic effects against KDR house flies, while conventional pyrethroids alone or mixed with other carbamate agents were not effective against KDR house flies. It was found to be extremely effective compared to other drugs. (3) 3′-Phenoxybenzyl as an insecticidal ingredient
2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate (vermethrin, compound (E)) and 2-isopropyl-4
- preparing a fumigant containing a predetermined amount of methylphenyl-N-methylcarbamate (compound (B)),
A test was conducted on cotton aphids in a greenhouse using the following method. Cultivation required Kiyuuri Product Species Kurume H type Plant height at test 1.3-1.5
m Ward system. Area House volume 400m 2 Survey date. Method Divide the house into 9 equal parts and height 1.0~
One location and one leaf of 1.5 m were selected and the number of parasitic cotton aphids was investigated. The number of surviving insects was investigated 24 hours after fumigation.
【表】
以下本発明の実施例を示す。
実施例 １
3′−フエノキシ−α′−シアノベンジル クリサ
ンセメート0.15ｇと２−イソプロピル−４−メチ
ルフエニル−Ｎ−メチルカーバメート0.15ｇと、
BHT0.04ｇを除虫菊抽出粕粉、木粉、でん粉等
の蚊取線香用基材99.66ｇと均一に混合し、常法
によつて蚊取線香を調製し、有効成分0.3％含有
蚊取線香を得る。
実施例 ３
3′−フエノキシベンジル ｄ−シス，トランス
−クリサンセメート７ｇ、２−イソプロピル−４
−メチルフエニル−Ｎ−メチルカーバメート３
ｇ、DBHQ10ｇ、ピペロニルブトキサイド10ｇ
にアセトンを加えて100mlとする。この殺虫液１
mlを30mm×60mm×1.5mmのパルプ板にしみ込ませ
たものを電気発熱体上に載置し、約160℃に加熱
し蒸散させる。
実施例 ５
（Ｓ）−3′−フエノキシ−α′−シアノベンジル
ｄ−シス−２，２−ジメチル−３−（２，２−
ジブロモビニル）シクロプロパンカルボキシレー
ト（デカメスリン）５ｇ、3′−フエノキシ−α′−
シアノベンジル２，２−ジメチル−３−（２，２
−ジクロロビニル）シクロプロパンカルボキシレ
ート５ｇ、２−イソプロピル−４−メチルフエニ
ル−Ｎ−メチルカーバメート15ｇ、DBH1ｇ，ア
ゾジカルボン酸アミド69ｇ及びCMC5ｇを加えて
均一に混合し、粒状に成型して加熱燻蒸剤を得
る。[Table] Examples of the present invention are shown below. Example 1 0.15 g of 3'-phenoxy-α'-cyanobenzyl chrysanthemate and 0.15 g of 2-isopropyl-4-methylphenyl-N-methylcarbamate,
A mosquito coil containing 0.3% of the active ingredient was prepared by uniformly mixing 0.04 g of BHT with 99.66 g of a base material for mosquito coils such as pyrethrum extracted lees powder, wood flour, and starch. obtain. Example 3 3'-phenoxybenzyl d-cis,trans-chrysansemate 7g, 2-isopropyl-4
-methylphenyl-N-methylcarbamate 3
g, DBHQ10g, piperonyl butoxide 10g
Add acetone to make 100ml. This insecticidal liquid 1
A 30 mm x 60 mm x 1.5 mm pulp board is soaked with ml of the solution, placed on an electric heating element, and heated to approximately 160°C to evaporate. Example 5 (S)-3'-phenoxy-α'-cyanobenzyl d-cis-2,2-dimethyl-3-(2,2-
dibromovinyl) cyclopropane carboxylate (decamethrin) 5g, 3'-phenoxy-α'-
Cyanobenzyl 2,2-dimethyl-3-(2,2
-Dichlorovinyl) cyclopropane carboxylate (5 g), 2-isopropyl-4-methylphenyl-N-methyl carbamate (15 g), DBH (1 g), azodicarboxamide (69 g) and CMC (5 g) were added, mixed uniformly, formed into granules, and heat fumigant was applied. obtain.
Claims (1)
原子を表し、Ｒは水素原子又はシアノ基を表す。）
で示されるピレスロイド系化合物の１種又は２種
と、２−イソプロピル−４−メチルフエニル−Ｎ
−メチルカーバメートとを９〜２：１〜８の組成
比で含有する混合殺虫組成物に、加熱燻蒸補助剤
としての酸化防止剤を上記混合殺虫組成物１に対
し、0.01〜1.0の組成比で含有することを特徴と
する加熱燻蒸用殺虫剤。[Claims] 1. General formula (In the formula, X represents a methyl group, a chloro atom, or a bromo atom, and R represents a hydrogen atom or a cyano group.)
One or two of the pyrethroid compounds shown and 2-isopropyl-4-methylphenyl-N
- Methyl carbamate in a composition ratio of 9 to 2:1 to 8, and an antioxidant as a heat fumigation aid in a composition ratio of 0.01 to 1.0 to the above mixed insecticidal composition 1. An insecticide for heat fumigation characterized by containing.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58184104A JPS6075403A (en) | 1983-09-30 | 1983-09-30 | Insecticide for thermal fumigation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58184104A JPS6075403A (en) | 1983-09-30 | 1983-09-30 | Insecticide for thermal fumigation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6075403A JPS6075403A (en) | 1985-04-27 |
| JPH048405B2 true JPH048405B2 (en) | 1992-02-17 |
Family
ID=16147459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58184104A Granted JPS6075403A (en) | 1983-09-30 | 1983-09-30 | Insecticide for thermal fumigation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6075403A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4861630A (en) * | 1971-12-06 | 1973-08-29 | ||
| JPS4947531A (en) * | 1972-05-25 | 1974-05-08 |
-
1983
- 1983-09-30 JP JP58184104A patent/JPS6075403A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4861630A (en) * | 1971-12-06 | 1973-08-29 | ||
| JPS4947531A (en) * | 1972-05-25 | 1974-05-08 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6075403A (en) | 1985-04-27 |
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