JP2000239262A - Triazole compound and its use - Google Patents
Triazole compound and its useInfo
- Publication number
- JP2000239262A JP2000239262A JP11038493A JP3849399A JP2000239262A JP 2000239262 A JP2000239262 A JP 2000239262A JP 11038493 A JP11038493 A JP 11038493A JP 3849399 A JP3849399 A JP 3849399A JP 2000239262 A JP2000239262 A JP 2000239262A
- Authority
- JP
- Japan
- Prior art keywords
- spp
- compound
- parts
- genus
- beetle
- 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.)
- Pending
Links
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- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 208000028454 lice infestation Diseases 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 241000238565 lobster Species 0.000 description 1
- 229960003951 masoprocol Drugs 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- MEBQXILRKZHVCX-UHFFFAOYSA-N methidathion Chemical compound COC1=NN(CSP(=S)(OC)OC)C(=O)S1 MEBQXILRKZHVCX-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960001952 metrifonate Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- XYFMGGWVGACNEC-UHFFFAOYSA-N n-carbamoyl-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(C(=O)N)C(=O)C1=CC=CC=C1 XYFMGGWVGACNEC-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000008048 phenylpyrazoles Chemical class 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Chemical class 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- UCWBKJOCRGQBNW-UHFFFAOYSA-M sodium;hydroxymethanesulfinate;dihydrate Chemical compound O.O.[Na+].OCS([O-])=O UCWBKJOCRGQBNW-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- PTOSZROYCHWBJI-UHFFFAOYSA-N thiadiazin-4-one Chemical compound O=C1C=CSN=N1 PTOSZROYCHWBJI-UHFFFAOYSA-N 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- 230000005068 transpiration Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DFQMKYUSAALDDY-MQEBUAKTSA-N trinactin Chemical compound C[C@@H]([C@@H]1CC[C@@H](O1)C[C@H](OC(=O)[C@H](C)[C@H]1CC[C@H](O1)C[C@H](CC)OC(=O)[C@@H](C)[C@@H]1CC[C@@H](O1)C[C@@H](CC)OC(=O)[C@@H]1C)CC)C(=O)O[C@@H](C)C[C@@H]2CC[C@H]1O2 DFQMKYUSAALDDY-MQEBUAKTSA-N 0.000 description 1
- DFQMKYUSAALDDY-UHFFFAOYSA-N trinactin Natural products CC1C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(CC)CC(O2)CCC2C(C)C(=O)OC(C)CC2CCC1O2 DFQMKYUSAALDDY-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【0001】[0001]
【発明の属する技術分野】本発明は、トリアゾール化合
物およびその用途に関する。[0001] The present invention relates to a triazole compound and its use.
【0002】[0002]
【従来の技術および発明が解決しようとする課題】特開
平10−158250号公報に、ある種のトリアゾール
化合物が優れた殺虫、殺ダニ、殺線虫効力を有すること
が記載されている。かかる化合物を、屋内、温室等の限
られた空間で使用する場合や、圃場等において使用する
場合も、使用形態によっては、その居住者や散布者に対
する高度な安全性が求められることから、哺乳動物に対
する安全性において、より優れる殺虫、殺ダニ、殺線虫
剤が望まれている。BACKGROUND OF THE INVENTION JP-A-10-158250 describes that certain triazole compounds have excellent insecticidal, acaricidal and nematicidal efficacy. When such compounds are used in limited spaces such as indoors and greenhouses, or when used in fields, etc., depending on the form of use, a high degree of safety is required for their residents and sprayers. There is a need for insecticides, acaricides, and nematicides that are superior in animal safety.
【0003】[0003]
【課題を解決するための手段】本発明者らは、上記状況
に鑑み、鋭意検討を重ねた結果、下記一般式 化2で示
されるトリアゾール化合物が、優れた殺虫、殺ダニ、殺
線虫効力を有するとともに、哺乳動物に対してより優れ
た安全性を有することを見出し、本発明に至った。即
ち、本発明は一般式 化2Means for Solving the Problems The present inventors have made intensive studies in view of the above situation, and as a result, have found that a triazole compound represented by the following general formula 2 has excellent insecticidal, acaricidal and nematicidal efficacy. And found that it has more excellent safety for mammals, and thus has accomplished the present invention. That is, the present invention provides a compound represented by the general formula:
【化2】 [式中、R1はエトキシカルボニル基またはメトキシカ
ルボニル基を表し、R1がエトキシカルボニル基の場
合、R2はエトキシメチル基を表し、R1がメトキシカル
ボニル基の場合、R2はエトキシメチル基またはメトキ
シメチル基を表す。]で示されるトリアゾール化合物
〔以下、本発明化合物と記す〕およびそれを有効成分と
して含有する殺虫、殺ダニ、殺線虫剤を提供する。Embedded image [Wherein, R 1 represents an ethoxycarbonyl group or a methoxycarbonyl group, R 1 represents an ethoxycarbonyl group, R 2 represents an ethoxymethyl group, and R 1 represents a methoxycarbonyl group, and R 2 represents an ethoxymethyl group. Or a methoxymethyl group. [Hereinafter referred to as the compound of the present invention] and an insecticide, acaricide, and nematicide containing the same as an active ingredient.
【0004】[0004]
【発明の実施の形態】本発明化合物は、具体的には前記
一般式 化2に於いて、R1がエトキシカルボニル基で
あり、R2がエトキシメチル基である、3−ジクロロフ
ルオロメチルスルフェニル−1−(2,6−ジクロロ−
4−トリフルオロメチルフェニル)−5−〔N−エトキ
シカルボニル−N−(エトキシメチル)アミノ〕−1,
2,4−トリアゾール、前記一般式 化2に於いて、R
1がメトキシカルボニル基であり、R2がメトキシメチル
基である、3−ジクロロフルオロメチルスルフェニル−
1−(2,6−ジクロロ−4−トリフルオロメチルフェ
ニル)−5−〔N−メトキシカルボニル−N−(メトキ
シメチル)アミノ〕−1,2,4−トリアゾール、およ
び、前記一般式 化2に於いて、R1がメトキシカルボ
ニル基であり、R2がエトキシメチル基である、3−ジ
クロロフルオロメチルスルフェニル−1−(2,6−ジ
クロロ−4−トリフルオロメチルフェニル)−5−〔N
−メトキシカルボニル−N−(エトキシメチル)アミ
ノ〕−1,2,4−トリアゾールである。BEST MODE FOR CARRYING OUT THE INVENTION The compound of the present invention is a compound represented by the general formula (2), wherein R 1 is an ethoxycarbonyl group and R 2 is an ethoxymethyl group. -1- (2,6-dichloro-
4-trifluoromethylphenyl) -5- [N-ethoxycarbonyl-N- (ethoxymethyl) amino] -1,
2,4-triazole, in the above general formula 2, R
3-dichlorofluoromethylsulfenyl- wherein 1 is a methoxycarbonyl group and R 2 is a methoxymethyl group
1- (2,6-dichloro-4-trifluoromethylphenyl) -5- [N-methoxycarbonyl-N- (methoxymethyl) amino] -1,2,4-triazole; Wherein R 1 is a methoxycarbonyl group and R 2 is an ethoxymethyl group, 3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -5- [N
-Methoxycarbonyl-N- (ethoxymethyl) amino] -1,2,4-triazole.
【0005】次に、本発明化合物の製造法について説明
する。本発明化合物は、例えば、下記(製造法)に従っ
て製造することができる。 (製造法)本発明化合物は、一般式 化3Next, a method for producing the compound of the present invention will be described. The compound of the present invention can be produced, for example, according to the following (production method). (Production method) The compound of the present invention has the general formula
【化3】 [式中、R1は前記と同じ意味を表す。]で示される化
合物と、一般式 化4Embedded image [Wherein, R 1 represents the same meaning as described above. And a compound represented by the general formula
【化4】 [式中、R21はメトキシメチル基またはエトキシメチル
基を表し、Xは脱離基(例えば、塩素原子、臭素原子、
よう素原子、トリフルオロメチルスルホニルオキシ基、
メタンスルホニルオキシ基等)を表す。]で示される化
合物とを通常溶媒中、塩基存在下、必要に応じて触媒の
存在下に、反応させることにより製造することができ
る。該反応の反応温度は、通常約−5℃〜150℃であ
り、反応時間は、通常1時間〜24時間である。反応に
供される試剤の量は、一般式 化3で示される化合物1
モルに対し、一般式 化1で示される化合物は通常1〜
10モルの割合であり、塩基の量は通常1モル〜大過剰
モルの割合である。塩基としては、例えば、水素化ナト
リウム、水素化カリウム、水酸化ナトリウム、水酸化カ
リウム、炭酸ナトリウム、炭酸カリウム等の無機塩基、
ナトリウムメトキシド、ナトリウムエトキシド等のアル
カリ金属アルコキシド、トリエチルアミン、ピリジン、
4−ジメチルアミノピリジン、N,N−ジメチルアニリ
ン等の有機塩基等があげられる。使用し得る反応溶媒と
しては、例えばヘキサン、ヘプタン、リグロイン、石油
エーテル等の脂肪族炭化水素溶媒、ベンゼン等の芳香族
炭化水素、ジクロロエタン、クロロベンゼン、ジクロロ
ベンゼン等のハロゲン化炭化水素溶媒、ジエチルエーテ
ル、ジイソプロピルエーテル、ジオキサン、テトラヒド
ロフラン、エチレングリコールジメチルエーテル等のエ
ーテル溶媒、アセトン、メチルエチルケトン、メチルイ
ソブチルケトン、イソホロン、シクロヘキサノン等のケ
トン溶媒、酢酸エチル、酢酸ブチル等のエステル溶媒、
アセトニトリル、イソブチロニトリル等のニトリル溶
媒、ニトロエタン、ニトロベンゼン等のニトロ化物、ホ
ルムアミド、N、N−ジメチルホルムアミド、N、N−
ジメチルアセトアミド等の酸アミド類、ジメチルスルホ
キシド、スルホラン等の硫黄化合物、水等あるいはそれ
らの混合物があげられる。必要に応じて用いられる触媒
としては、クラウンエーテル等があげられる。反応終了
後の反応液は、これを水に注加し、これを有機溶媒にて
抽出し、該有機層を濃縮する等の後処理操作を行い、目
的の本発明化合物を得ることができる。該化合物は、ク
ロマトグラフィー、再結晶等の操作に付すこともでき
る。Embedded image [Wherein, R 21 represents a methoxymethyl group or an ethoxymethyl group, and X represents a leaving group (for example, a chlorine atom, a bromine atom,
Iodine atom, trifluoromethylsulfonyloxy group,
Methanesulfonyloxy group). And the compound represented by the formula (I) is usually reacted in a solvent in the presence of a base and, if necessary, in the presence of a catalyst. The reaction temperature of the reaction is usually about -5 ° C to 150 ° C, and the reaction time is usually 1 hour to 24 hours. The amount of the reagent used for the reaction is determined by the amount of the compound 1 represented by the general formula (3).
The compound represented by the general formula 1 is usually 1 to
The ratio is 10 moles, and the amount of the base is usually from 1 mole to a large excess mole. As the base, for example, inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate;
Sodium methoxide, alkali metal alkoxides such as sodium ethoxide, triethylamine, pyridine,
Organic bases such as 4-dimethylaminopyridine, N, N-dimethylaniline and the like can be mentioned. Reaction solvents that can be used include, for example, hexane, heptane, ligroin, aliphatic hydrocarbon solvents such as petroleum ether, aromatic hydrocarbons such as benzene, dichloroethane, chlorobenzene, halogenated hydrocarbon solvents such as dichlorobenzene, diethyl ether, Ether solvents such as diisopropyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, ketone solvents such as cyclohexanone, ethyl acetate, ester solvents such as butyl acetate,
Acetonitrile, nitrile solvents such as isobutyronitrile, nitrates such as nitroethane and nitrobenzene, formamide, N, N-dimethylformamide, N, N-
Examples thereof include acid amides such as dimethylacetamide, sulfur compounds such as dimethylsulfoxide and sulfolane, water and the like, and mixtures thereof. Examples of the catalyst used as needed include crown ether and the like. After completion of the reaction, the reaction mixture is subjected to post-treatment operations such as pouring the mixture into water, extracting the mixture with an organic solvent, and concentrating the organic layer to obtain the target compound of the present invention. The compound can be subjected to operations such as chromatography and recrystallization.
【0006】一般式 化3で示される化合物は、5−ア
ミノ−3−ジクロロフルオロメチルスルフェニル−1−
(2,6−ジクロロ−4−トリフルオロメチルフェニ
ル)−1,2,4−トリアゾールと一般式 化3The compound represented by the general formula (3) is 5-amino-3-dichlorofluoromethylsulfenyl-1-
(2,6-dichloro-4-trifluoromethylphenyl) -1,2,4-triazole and a compound of the general formula 3
【化5】 [式中、R1およびXは前記と同じ意味を表す。]で示
される化合物とを通常溶媒中、塩基存在下、必要に応じ
て触媒の存在下に、反応させることにより製造すること
ができる。該反応の反応温度は、通常約−5℃〜150
℃であり、反応時間は、通常1時間〜24時間である。
反応に供される試剤の量は、5−アミノ−3−ジクロロ
フルオロメチルスルフェニル−1−(2,6−ジクロロ
−4−トリフルオロメチルフェニル)−1,2,4−トリ
アゾール1モルに対し、一般式 化5で示される化合物
は通常1〜10モルの割合であり、塩基の量は通常1モ
ル〜大過剰モルの割合である。塩基としては、例えば、
水素化ナトリウム、水素化カリウム、水酸化ナトリウ
ム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム等
の無機塩基、ナトリウムメトキシド、ナトリウムエトキ
シド等のアルカリ金属アルコキシド、トリエチルアミ
ン、ピリジン、4−ジメチルアミノピリジン、N,N−
ジメチルアニリン等の有機塩基等があげられる。使用し
得る反応溶媒としては、例えばヘキサン、ヘプタン、リ
グロイン、石油エーテル等の脂肪族炭化水素溶媒、ベン
ゼン等の芳香族炭化水素、ジクロロエタン、クロロベン
ゼン、ジクロロベンゼン等のハロゲン化炭化水素溶媒、
ジエチルエーテル、ジイソプロピルエーテル、ジオキサ
ン、テトラヒドロフラン、エチレングリコールジメチル
エーテル等のエーテル溶媒、アセトン、メチルエチルケ
トン、メチルイソブチルケトン、イソホロン、シクロヘ
キサノン等のケトン溶媒、酢酸エチル、酢酸ブチル等の
エステル溶媒、アセトニトリル、イソブチロニトリル等
のニトリル溶媒、ニトロエタン、ニトロベンゼン等のニ
トロ化物、ホルムアミド、N、N−ジメチルホルムアミ
ド、N、N−ジメチルアセトアミド等の酸アミド類、ジ
メチルスルホキシド、スルホラン等の硫黄化合物、水等
あるいはそれらの混合物があげられる。必要に応じて用
いられる触媒としては、クラウンエーテル等があげられ
る。反応終了後の反応液は、これを水に注加し、これを
有機溶媒にて抽出し、該有機層を濃縮する等の後処理操
作を行い、目的の化合物を得ることができる。該化合物
は、クロマトグラフィー、再結晶等の操作に付すことも
できる。Embedded image [Wherein, R 1 and X represent the same meaning as described above. And the compound represented by the formula (I) is usually reacted in a solvent in the presence of a base and, if necessary, in the presence of a catalyst. The reaction temperature of the reaction is usually about -5 ° C to 150 ° C.
° C, and the reaction time is usually 1 hour to 24 hours.
The amount of the reagent used for the reaction is based on 1 mol of 5-amino-3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -1,2,4-triazole. The compound represented by the general formula 5 is usually in a proportion of 1 to 10 mol, and the amount of the base is usually in a proportion of 1 mol to a large excess mol. As the base, for example,
Inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc., alkali metal alkoxides such as sodium methoxide, sodium ethoxide, triethylamine, pyridine, 4-dimethylaminopyridine, N , N-
Organic bases such as dimethylaniline and the like can be mentioned. As a reaction solvent that can be used, for example, hexane, heptane, ligroin, aliphatic hydrocarbon solvents such as petroleum ether, aromatic hydrocarbons such as benzene, dichloroethane, chlorobenzene, halogenated hydrocarbon solvents such as dichlorobenzene,
Ether solvents such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran and ethylene glycol dimethyl ether; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone and cyclohexanone; ester solvents such as ethyl acetate and butyl acetate; acetonitrile and isobutyronitrile Nitrile solvents such as nitroethane, nitrobenzene, etc., acid amides such as formamide, N, N-dimethylformamide, N, N-dimethylacetamide, sulfur compounds such as dimethyl sulfoxide, sulfolane, water and the like, and mixtures thereof. can give. Examples of the catalyst used as needed include crown ether and the like. After the completion of the reaction, the reaction solution is poured into water, extracted with an organic solvent, and subjected to a post-treatment operation such as concentration of the organic layer to obtain a target compound. The compound can be subjected to operations such as chromatography and recrystallization.
【0007】5−アミノ−3−ジクロロフルオロメチル
スルフェニル−1−(2,6−ジクロロ−4−トリフル
オロメチルフェニル)−1,2,4−トリアゾールは、下
記(方法1)または(方法2)に従って製造することが
できる。 (方法1)3,3′−ジ〔5−アミノ−1−(2,6−ジ
クロロ−4−トリフルオロメチルフェニル)−1,2,4
−トリアゾリル〕ジスルフィドと、トリクロロフルオロ
メタンまたはブロモジクロロフルオロメタンとを、無溶
媒または溶媒中、還元剤の存在下に反応させることによ
り製造することができる。該反応の反応温度は、通常約
−20℃〜150℃であり、反応時間は、通常1時間〜
24時間である。反応に供される試剤の量は、3,3′
−ジ〔5−アミノ−1−(2,6−ジクロロ−4−トリ
フルオロメチルフェニル)−1,2,4−トリアゾリル〕
ジスルフィド1モルに対し、トリクロロフルオロメタン
またはブロモジクロロフルオロメタンは通常2モル〜大
過剰モルの割合であり、還元剤の量は通常2〜6モルの
割合である。還元剤としては、ヒドロキシメタンスルフ
ィン酸塩(ヒドロキシメタンスルフィナートアニオンと
種々の陽イオンとから形成される塩。例えば、ヒドロキ
シメタンスルフィン酸ナトリウム等のヒドロキシメタン
スルフィン酸アルカリ金属塩等)、亜ジチオン酸アルカ
リ金属塩(例えば、亜ジチオン酸ナトリウム等)等があ
げられる。使用し得る反応溶媒としては、例えばヘキサ
ン、ヘプタン、リグロイン、石油エ−テル等の脂肪族炭
化水素溶媒、ベンゼン等の芳香族炭化水素、ジクロロエ
タン、クロロベンゼン、ジクロロベンゼン等のハロゲン
化炭化水素溶媒、ジエチルエ−テル、ジイソプロピルエ
−テル、ジオキサン、テトラヒドロフラン、エチレング
リコ−ルジメチルエ−テル等のエ−テル溶媒、アセト
ン、メチルエチルケトン、メチルイソブチルケトン、イ
ソホロン、シクロヘキサノン等のケトン溶媒、酢酸エチ
ル、酢酸ブチル等のエステル溶媒、アセトニトリル、イ
ソブチロニトリル等のニトリル溶媒、ニトロエタン、ニ
トロベンゼン等のニトロ化物、ホルムアミド、N、N−
ジメチルホルムアミド、N、N−ジメチルアセトアミド
等の酸アミド類、ジメチルスルホキシド、スルホラン等
の硫黄化合物、水等あるいはそれらの混合物があげられ
る。反応終了後の反応液は、これを水に注加し、これを
有機溶媒にて抽出し、該有機層を濃縮する等の後処理操
作を行い、目的の化合物を得ることができる。該化合物
は、クロマトグラフィ−、再結晶等の操作に付すことも
できる。[0007] 5-amino-3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -1,2,4-triazole is prepared by the following (method 1) or (method 2). ). (Method 1) 3,3'-di [5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -1,2,4
[Triazolyl] disulfide and trichlorofluoromethane or bromodichlorofluoromethane, in the absence of a solvent or in a solvent, in the presence of a reducing agent. The reaction temperature of the reaction is generally about −20 ° C. to 150 ° C., and the reaction time is generally 1 hour to
24 hours. The amount of reagent used for the reaction is 3,3 '
-Di [5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -1,2,4-triazolyl]
Trichlorofluoromethane or bromodichlorofluoromethane is usually in a proportion of 2 mol to a large excess mol per mol of disulfide, and the amount of the reducing agent is usually 2 to 6 mol. Examples of the reducing agent include hydroxymethanesulfinate (a salt formed from hydroxymethanesulfinate anion and various cations; for example, alkali metal salts of hydroxymethanesulfinate such as sodium hydroxymethanesulfinate), dithionite Acid alkali metal salts (eg, sodium dithionite and the like) and the like. Examples of usable reaction solvents include aliphatic hydrocarbon solvents such as hexane, heptane, ligroin, petroleum ether, aromatic hydrocarbons such as benzene, halogenated hydrocarbon solvents such as dichloroethane, chlorobenzene and dichlorobenzene, and diethyl ether. Ether solvents such as ter, diisopropyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone and cyclohexanone, and ester solvents such as ethyl acetate and butyl acetate. , Acetonitrile, nitrile solvents such as isobutyronitrile, nitrates such as nitroethane and nitrobenzene, formamide, N, N-
Examples thereof include acid amides such as dimethylformamide and N, N-dimethylacetamide; sulfur compounds such as dimethylsulfoxide and sulfolane; water; and mixtures thereof. After the completion of the reaction, the reaction solution is poured into water, extracted with an organic solvent, and subjected to a post-treatment operation such as concentration of the organic layer to obtain a target compound. The compound can be subjected to operations such as chromatography and recrystallization.
【0008】(方法2)5−アミノ−1−(2,6−ジ
クロロ−4−トリフルオロメチルフェニル)−3−メル
カプト−1,2,4−トリアゾールと、トリクロロフルオ
ロメタンまたはブロモジクロロフルオロメタンとを無溶
媒または溶媒中、還元剤の存在下に反応させることによ
り製造することができる。該反応の反応温度は、通常約
−20℃〜150℃であり、反応時間は、通常1時間〜
24時間である。反応に供される試剤の量は、5−アミ
ノ−1−(2,6−ジクロロ−4−トリフルオロメチル
フェニル)−3−メルカプト−1,2,4−トリアゾール
1モルに対し、トリクロロフルオロメタンまたはブロモ
ジクロロフルオロメタンは通常1モル〜大過剰モルの割
合であり、還元剤の量は通常1〜6モルの割合である。
還元剤としては、ヒドロキシメタンスルフィン酸塩(ヒ
ドロキシメタンスルフィナートアニオンと種々の陽イオ
ンとから形成される塩。例えば、ヒドロキシメタンスル
フィン酸ナトリウム等のヒドロキシメタンスルフィン酸
アルカリ金属塩等)、亜ジチオン酸アルカリ金属塩(例
えば、亜ジチオン酸ナトリウム等)等があげられる。使
用し得る反応溶媒としては、例えばヘキサン、ヘプタ
ン、リグロイン、石油エ−テル等の脂肪族炭化水素溶
媒、ベンゼン等の芳香族炭化水素、ジクロロエタン、ク
ロロベンゼン、ジクロロベンゼン等のハロゲン化炭化水
素溶媒、ジエチルエ−テル、ジイソプロピルエ−テル、
ジオキサン、テトラヒドロフラン、エチレングリコ−ル
ジメチルエ−テル等のエ−テル溶媒、アセトン、メチル
エチルケトン、メチルイソブチルケトン、イソホロン、
シクロヘキサノン等のケトン溶媒、酢酸エチル、酢酸ブ
チル等のエステル溶媒、アセトニトリル、イソブチロニ
トリル等のニトリル溶媒、ニトロエタン、ニトロベンゼ
ン等のニトロ化物、ホルムアミド、N、N−ジメチルホ
ルムアミド、N、N−ジメチルアセトアミド等の酸アミ
ド類、ジメチルスルホキシド、スルホラン等の硫黄化合
物、水等あるいはそれらの混合物があげられる。反応終
了後の反応液は、これを水に注加し、これを有機溶媒に
て抽出し、該有機層を濃縮する等の後処理操作を行い、
目的の化合物を得ることができる。該化合物は、クロマ
トグラフィ−、再結晶等の操作に付すこともできる。(Method 2) 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3-mercapto-1,2,4-triazole, trichlorofluoromethane or bromodichlorofluoromethane Can be produced in the absence of a solvent or in a solvent in the presence of a reducing agent. The reaction temperature of the reaction is generally about −20 ° C. to 150 ° C., and the reaction time is generally 1 hour to
24 hours. The amount of the reagent used in the reaction was as follows: 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3-mercapto-1,2,4-triazole and 1 mol of trichlorofluoromethane. Alternatively, bromodichlorofluoromethane is usually in a proportion of 1 mol to a large excess mol, and the amount of the reducing agent is usually 1 to 6 mol.
Examples of the reducing agent include hydroxymethanesulfinate (a salt formed from hydroxymethanesulfinate anion and various cations; for example, alkali metal salts of hydroxymethanesulfinate such as sodium hydroxymethanesulfinate), dithionite Acid alkali metal salts (eg, sodium dithionite and the like) and the like. Examples of usable reaction solvents include aliphatic hydrocarbon solvents such as hexane, heptane, ligroin, petroleum ether, aromatic hydrocarbons such as benzene, halogenated hydrocarbon solvents such as dichloroethane, chlorobenzene and dichlorobenzene, and diethyl ether. -Ter, diisopropyl ether,
Ether solvents such as dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone,
Ketone solvents such as cyclohexanone, ester solvents such as ethyl acetate and butyl acetate, nitrile solvents such as acetonitrile and isobutyronitrile, nitrates such as nitroethane and nitrobenzene, formamide, N, N-dimethylformamide, N, N-dimethylacetamide Acid amides, sulfur compounds such as dimethyl sulfoxide and sulfolane, water and the like, and mixtures thereof. After completion of the reaction, the reaction solution was poured into water, extracted with an organic solvent, and subjected to post-treatment operations such as concentration of the organic layer.
The desired compound can be obtained. The compound can be subjected to operations such as chromatography and recrystallization.
【0009】5−アミノ−3−ジクロロフルオロメチル
スルフェニル−1−(2,6−ジクロロ−4−トリフル
オロメチルフェニル)−1,2,4−トリアゾールを製造
する際の原料となる3,3′−ジ〔5−アミノ−1−
(2,6−ジクロロ−4−トリフルオロメチルフェニ
ル)−1,2,4−トリアゾリル〕ジスルフィドおよび5
−アミノ−1−(2,6−ジクロロ−4−トリフルオロ
メチルフェニル)−3−メルカプト−1,2,4−トリア
ゾールは、例えば特開平10−158250号公報に記
載された方法に準じてそれぞれ製造することができる。
トリクロロフルオロメタンは、例えば市販の試薬(例え
ば、シグマ アルドリッチ ジャパン社製等)を使用する
ことができる。ブロモジクロロフルオロメタンは、例え
ばJ.Fluorine Chem.、第20巻、89
−97頁(1982年)に記載の方法に準じて製造する
ことができる。3,3,3 which is a raw material for producing 5-amino-3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -1,2,4-triazole '-Di [5-amino-1-
(2,6-dichloro-4-trifluoromethylphenyl) -1,2,4-triazolyl] disulfide and 5
-Amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3-mercapto-1,2,4-triazole can be obtained, for example, according to the method described in JP-A-10-158250. Can be manufactured.
As the trichlorofluoromethane, for example, a commercially available reagent (for example, Sigma-Aldrich Japan Co., Ltd.) can be used. Bromodichlorofluoromethane is described, for example, in J. Am. Fluorine Chem. , Volume 20, 89
-97 (1982).
【0010】本発明化合物が防除効力を発揮する有害昆
虫類、有害ダニ類および有害線虫類としては、例えば、
下記のものがあげられる。Oniscus asell
us、Armadillidium vulgare、
(オカダンゴムシ)、Porcellio scabe
r等の等脚目(Isopoda)害虫;Blanilu
s guttulatus(ヤスデの一種)などの倍脚
目(Diplopoda)害虫;Geophilus
carpophagus、Scutigera sp
p.、Scolopendra subspinipe
s(トビズムカデ)、Thereunema spp.
(ゲジの仲間)などの唇脚目(Chilopoda)害
虫;Scutigerellaimmaculataな
どの結合目(Symphyla)害虫;Ctenole
pisma villosa(ヤマトシミ)、Lepi
sma saccharina(キボシアリシミの一
種)などの総尾目(Thysanura)害虫;Tro
gium pulsatorium(コナチャタテ)な
どの噛虫目(Psocoptera)害虫;Onych
iurus armatus(シロトビムシの一種)な
どの粘管目(Collembola)害虫;ムカシシロ
アリ科(Mastotermitidae)、Zoot
ermopsis属、Archotermopsis
属、オオシロアリ(Hodotermopsis ja
ponica)等のHodotermopsis属、P
orotetmes属等のオオシロアリ科(Termo
psidae)、Kalotermes属、コウシュン
シロアリ(Neotermes koshuensi
s)等のNeotermes属、ダイコクシロアリ(C
ryptotermes domesticus)等の
Cryptotermes属、アメリカカンザイシロア
リ(Incisitermes minor)等のIn
cisitermes属、サツマシロアリ(Glypt
otermes satsumaensis)、ナカジ
マシロアリ(G.nakajimai)、カタンシロア
リ(G.fuscus)等のGlyptotermes
属等のレイビシロアリ科(Kalotermitida
e)、Hodotermes属、Microhodot
ermes属、Anacanthotermes属等の
シュウカクシロアリ科(Hodotermitida
e)、ヤマトシロアリ(Retitulitermes
speratus)、カンモンシロアリ(R.s
p)、キアシシロアリ(R.flaviceps)、ア
マミシロアリ(R.miyatakei)等のReti
culitermes属、Heterotermes
属、イエシロアリ(Coptotermes form
osanus)等のCoptotermes属、Sch
edolinotermes属等のミゾガシラシロアリ
科(Rhinotermitidae)、ノコギリシロ
アリ科(Serritermitidae)、Amit
ermes属、Drepanotermes属、Hop
italitermes属、Trinerviterm
es属、Macrotermes属、タイワンシロアリ
(Odontotermes formosanus)
等のOdontotermes属、Microterm
es属、タカサゴシロアリ(Nasutitermes
takasagoensis)等のNasutiter
mes属、ニトベシロアリ(Pericapriter
mes nitobei)等のPericaprite
rmes属、Anoplotermes属等のシロアリ
科(Termitidae)などの等翅目(Isopt
era)害虫;The harmful insects, harmful mites and harmful nematodes to which the compound of the present invention exerts control effects include, for example,
The following are listed. Oniscus asell
us, Armadillidium vulgare,
(Polypod beetle), Porcellio scabe
Isopoda pests such as r;
diplopoda pests such as s guttulatus (a kind of millipede); Geophilus
carpophagus, Scutigera sp
p. , Scolopendra subspinipe
s (Tobisumkade), Thereunema spp.
(Chiropoda) pests such as (comrades of gezi); Symphyla pests such as Scutigellaella immaculata; Ctenole
Pisma villasa (Yamatoshimi), Lepi
Thysanura pests, such as sma saccharina (a kind of red croak spot); Tro
Psocoptera pests such as gium pulsatorium; Onych
Colembola pests such as urus armathus (a kind of white-spotted beetle); Ranidae (Mastertermitidae), Zoot
genus thermopsis, Archotermopsis
Genus, Termite (Hodotermopsis ja)
genus Hodothermopsis, P. ponica)
Termites of the genus orotetmes (Termo)
psidae), genus Kalotermes, Neotermes koshuensi
s), Neotermes, and termites (C)
genus Cryptotermes such as ryptotermes domesticus, and In such as Incitermes minor.
genus cistermes, termite (Glypt
Glyptotermes such as Otermes satsumaensis, G. nakajimai, and G. fuscus.
Genus, etc. (Kalotermitida)
e), genus Hodotetermes, Microhotot
ermes, Anacanthotermes, etc.
e), termites (Retitulitermes)
Speratus), termites (R.s.)
p), Reti such as the termite (R. flavoriceps) and the amami termite (R. miyatakei)
genus cultermes, Heterotermes
Genus, termite (Coptotermes form)
osanus) and the genus Copttermes, Sch
Rhotermitidae, Serotermitidae, Amit
ermes, Drepanotermes, Hop
genus italitermes, Trinerviterm
es genus, Macrotermes genus, Chinese termite (Odontotermes formosanus)
Odontotermes genus, Microterm
es genus, Takasago termites (Nasutermes)
Takasugoensis)
genus mes, Nitobe termite (Pericapriter
mes nitobei) etc.
Isopteridae (Isopt) such as termites (Termitidae) of the genus Rmes and Anoplottermes
era) pests;
【0011】Blatta orientalis(ト
ウヨウゴキブリ)、Periplaneta amer
icana(ワモンゴキブリ)、P.fuligino
sa(クロゴキブリ)、Leucophaea mad
erae(マデラゴキブリ)、Blattella g
ermanica(チャバネゴキブリ)、などの網翅目
(Dictyoptera)害虫;Gryllotal
pa spp.(ケラの一種)、Acheta dom
esticus(イエコオロギ)、Teleogryl
lus emma(エンマコオロギ)、Locusta
migratoria(トノサマバッタ)、Mela
noplus differentialis(バッタ
の一種)、Schistocerca gregari
a(サバクワタリバッタ)などの直翅目(Orthop
tera)害虫;Labidurariparia(オ
オハサミムシ)、Forficula auricul
aria(クギヌキハサミムシの一種)などの革翅目
(Dermaptera)害虫;Phthirus p
ubis(ケジラミ)、Pediculus huma
nus(アタマジラミ)、Haematopinus
suls(ブタジラミ)、Haematopinus
eurysternus(ウシジラミ)、Damali
nia ovis(ヒツジジラミ)、Linognat
hus spp.(ホソジラミの一種)、Soleno
potes spp.(ホソジラミの一種)などのシラ
ミ目(Anoplura)害虫;Trichodect
es spp.(ケモノハジラミの一種)、Trome
nopon spp.(ケモノタンカクハジラミの一
種)、Bovicola spp.(ケモノハジラミの
一種)、Felicola spp.(ケモノハジラミ
の一種)などの食毛目(Mallophaga)害虫;
Frankliniella intonsa(ヒラズ
ハナアザミウマ)、Thrips tabaci(ネギ
アザミウマ)、T.palmi(ミナミキイロアザミウ
マ)などの総翅目(Thysanoptera)害虫;
Nezara spp.(アオクサカメムシの一種)、
Eurygaster spp.(チャイロカメムシの
一種)、Dysdercus intermedius
(ホシカメムシの一種)、Cimex lectula
rius(トコジラミ)、Triatoma spp.
(サシガメの一種)、Rhodnius prolix
us(オオサシガメの一種)、Nezara ante
nnata(マオクサマメムシ)、Cletus pu
netiger(ホソハリカメムシ)などの異翅亜目
(Heteroptera)害虫;Aleurocan
thus spiniferus(ミカントゲコナジラ
ミ)、Bemisiatabaci(タバココナジラ
ミ)、Trialeurodes vaporario
rum(オンシツコナジラミ)、Aphis goss
ypii(ワタアブラムシ)、Brevocoryne
brassicae(ダイコンアブラムシ)、Cry
ptomyzus ribis(アブラムシの一種)、
Aphis fabae、Macrosiphum e
uphorbiae(チューリップヒゲナガアブラム
シ)、Myzus persicae(モモアカアブラ
ムシ)、Phorodon humuli(ホップイボ
アブラムシ)、Empoasca spp.(ヒメヨコ
バイの一種)、Nephotettix cincti
ceps(ツマグロヨコバイ)、Lecanium c
orni(ミズキカタカイガラムシ)、Saisset
ia oleae(オリーブカタカイガラムシ)、La
odelphax striatellus(ヒメトビ
ウンカ)、Nilaparvata lugens(ト
ビイロウンカ)、Aonidiellaauranti
i(アカマルカイガラムシ)、Aspidiotus
hederae(シロマルカイガラムシ)、Pseud
ococcus spp.(クワコナカイガラムシの一
種)、Psylla spp.(キジラミの一種)、P
hylloxera vastatrix(ブドウネア
ブラムシ)などの同翅亜目(Homoptera)害
虫;[0011] Blatta orientalis (Periplaneta americana), Periplaneta amer
icana (Water cockroach), p. fuligino
sa (black cockroach), Leucophaea mad
erae (Madela cockroach), Blattella g
ermanica (German cockroaches), such as Dictoptera pests;
pa spp. (A kind of vignetting), Acheta dom
esticus, Teleogryl
rus emma (Emaku cricket), Locusta
migratoria, Mela
noplus differentialialis (a kind of grasshopper), Schistocerca gregari
Orthop (Orthop)
tera) pests; Labidurariparia (Toothbill beetle), Forficula auricul
Dermaptera pests, such as aria (a kind of earwigs); Phthirus p
ubis, pediculus huma
nus (head lice), Haematopinus
suls (porcine lice), Haematopinus
eurysternus (bovine lice), Damali
nia obis (sheep lice), Linognat
hus spp. (A kind of white lice), Soleno
potes spp. (Anoplura) pests such as (a kind of white lice); Trichodict
es spp. (A kind of louse louse), Trome
nopon spp. (A kind of white lice), Bovicola spp. (A kind of psyllid lice), Felicola spp. (Mallophaga) pests such as (a kind of lice)
Frankliniella intonsa (Thysanoptera: Thrips), Trips tabaci (Thysanoptera: Thrips); Thysanoptera pests such as palmi (Thysanoptera: Thrips);
Nezara spp. (A kind of green stink bug),
Eurygaster spp. (A kind of stink bug), Dysdercus intermedius
(A kind of stink bug), Cimex lectula
rius (bed bugs), Triatoma spp.
(A kind of turtle), Rhodnius prolix
us (a kind of horse turtle), Nezara ante
nnata (Coleoptera), Cletus pu
Heteroptera pests, such as netiger (Heteroptera); Aleurocan
thus spiniferus (whiteflies), Bemisiatabaci (whiteflies), Trialeurodes vapororio
rum (Aphid whiteflies), Aphis goss
ypii (cotton aphid), Brevocoryne
brassicae (radish aphid), Cry
ptomyzus ribis (a kind of aphid),
Aphis Fabae, Macrosiphume
uphorbiae (tulip beetle aphid), Myzus persicae (peach peach aphid), Phorodon humuli (hope wart aphid), Empoasca spp. (A kind of leafhopper), Nephotettix cincti
ceps (Leafhopper), Lecanium c
orni (Maduki beetle), Saiset
ia oleae (olive beetle), La
odelphax striatellas (Pyrocarpaceae), Nilaparvata lugens (Pyrocarpaceae), Aonidiella lauranti
i (Red-tailed scale), Aspidiotus
hederae, Pseudo
ococcus spp. (A kind of stag beetle), Psylla spp. (A kind of lice), P
Homoptera pests, such as hyloxera vasatrix (grape aphids);
【0012】Pectinophora gossyp
iella(ワタアカミムシ)、Lithocolle
tis blancardella(ホソガの一種)、
Plutella xylostella(コナガ)、
Malacosoma neustria(オビカレ
ハ)、Euproctis subflava(ドク
ガ)、Lymantria dispar(マイマイ
ガ)、Bucculatrixpyrivorella
(ナシチビガ)、Phyllocnistis cit
rella(ミカンハモグリガ)、Agrotis s
pp.(カブラヤガの一種)、Euxoa spp.
(ヤガの一種)、Earias insulana(ワ
タリンガの一種)、Heliothis spp.(ワ
タミムシの一種)、Spodoptera exigu
a(シロイチモジヨトウ)、S.litura(ハスモ
ンヨトウ)、Spodoptera spp.(ヨトウ
の一種)、Mamestra brassicae(ヨ
トウガ)、Trichoplusia ni(ウワバの
一種)、Carpocapsa pomonella
(コドリンガ)、Pieris spp.(モンシロチ
ョウの一種)、Chilo spp.(ニカメイガの一
種)、Pyrausta nubilalis(メイガ
の一種)、Ephestia kuehniella
(スジコナマダラメイガ)、Galleria mel
lonella(ハチミツガ)、Tineolabis
selliella(コイガ)、Tenea tran
slucens(イガ)、Homona magnan
ima(チャハマキ)、Tortrixviridan
a(ハマキの一種)などの鱗翅目(Lepidopte
ra)害虫;Anobium punctatum(シ
バンムシの一種)、Rhizopertha domi
nica(コナナガシンクイ)、Acanthosce
lides obtectus(インゲンマメゾウム
シ)、Agelasticaalni(ハンノキハムシ
の一種)、Leptinotarsa decemli
neata(コロラドハムシ)、Phaedon co
chleariae(ハムシの一種)、Diabrot
ica spp.(コーンルートワームの一種)、Ps
ylliodes angusticollis(ナス
ノミハムシ)、Phyllotretastriola
ta(キスジノミハムシ)、Epilachna sp
p.(ニジュウヤホシテントウの一種)、Atomar
iaspp.(キスイムシの一種)、Oryzaeph
ilus surinamensis(ノコギリヒラタ
ムシ)、Anthonomus spp.(ハナゾウム
シの一種)、Sitophilus spp.(コクゾ
ウムシの一種)、Otiorhynchus sulc
atus(キンケクチブトゾウムシ)、Cosmopo
lites sordidus(バショウオサゾウム
シ)、Ceuthorhyncidius albos
uturalis(ダイコンゾウムシ)、Hypera
postica(アルファルファタコゾウムシ)、D
ermestes spp.カツオブシムシの一種)、
Trogoderma spp.(マダラカツオブシム
シの一種)、Attagenus unicolor
(ヒメカツオブシムシ)、Lyctus dentat
um(アラゲヒラタキクイムシ)、L.planico
llis(アメリカヒラタキクイムシ)、L.sine
nsis(ケヤキヒラタキクイムシ)、L.linea
ris(ナラヒラタキクイムシ)、L.brunneu
s(ヒラタキクイムシ)、L.africanus(ア
フリカヒラタキクイムシ)等のヒラタキクイムシ科(L
yctridae)、Meligethes aene
us(ケシキスイの一種)、Ptinusspp.(ヒ
ョウホンムシの一種)、Gibbium psyllo
ides(セマルヒョウホンムシ)、Triboliu
m spp.(コクヌストモドキの一種)、Teneb
rio molitor(チャイロコメノゴミムシダマ
シ)、Agriotes spp.(ムナボソコメツキ
の一種)、Melolontha mololonth
a(コフキコガネの一種)、Xyleborus属、S
colytoplatypus属等のキクイムシ科(S
colytidae)、Monochamus属、Hy
lotrupes属、Hesperophanus属、
Chlorophorus属、Palaeocalli
dium属、Semanotus属、Purpuric
enus属、Stromatium属等のカミキリムシ
科(Cerambycidae)、Crossotar
sus属、Platypus属等のナガキクイムシ科
(Platypodidae)、Dinoderus
属、Bostrychus属、Sinoderus属等
のナガシンクイムシ科(Bostrychidae)、
Ernobius属、Anobium属、Xyleti
nus属、Xestobium属、Ptilinus
属、Nicobium属、Ptilineurus属等
のシバンムシ科(Anobiidae)、タマムシ科
(Buprestidae)などの鞘翅目(Coleo
ptera)害虫;Diprion spp.(クロホ
シハバチの一種)、Hoplocampa spp.
(ハバチの一種)、Lasius spp.(クロクサ
アリの一種)、Formica japonica(ク
ロヤマアリ)、Vespa spp.(スズメバチの一
種)、Urocerus属、Sirex属等のキバチ科
(Siricidae)などの膜翅目(Hymenop
tera)害虫;Aedes spp.(シマカの一
種)、Anopheles spp.(ハマダラカの一
種)、Culex spp.(イエカの一種)、Dro
sophila melanogaster(キイロシ
ョウジョウバエの一種)、Musca domesti
ca(イエバエ)、Fannia spp.(ヒメイエ
バエの一種)、Calliphora spp.(クロ
バエの一種)、Lucilia spp.(キンバエの
一種)、Chrysomya spp.(オビキンバエ
の一種)、Cuterebra spp.、Gastr
ophilusspp.(ウマバエの一種)、Stom
oxys spp.(サシバエの一種)、Oestru
s spp.(ヒツジバエの一種)、Hypoderm
a spp.(ウシバエの一種)、Tabanus s
pp.(アブの一種)、Bibio hortulan
us(ケバエの一種)、Pegomyia hyosc
yami(ハナバエの一種)、Ceratitis c
apitata(チチュウカイミバエ)、Dacus
dorsalis(ミカンコミバエ)、Tipula
paludosa(ガガンボの一種)、Simuliu
m spp.(ブユの一種)、Eusimulium
spp.、Phlebotomus spp.(サシチ
ョウバエの一種)、Culicoides spp.
(ヌカカの一種)、Chrysops spp.(メク
ラアブの一種)、Haematopota spp.
(サシバエの一種)、Braula spp.(ミツバ
チシラミバエの一種)、Morellia spp.
(ハナバエの一種)、Glossina spp.(ツ
ェツェバエの一種)、Wohlfahrtia sp
p.、Sarcophaga spp.(ニクバエの一
種)、Lipoptena spp.(シラミバエの一
種)、Melophagus spp.(シラミバエの
一種)、Muscina spp.(オオイエバエの一
種)などの双翅目(Diptera)害虫;Xenop
sylla cheopis(ケオプスネズミノミ)、
Ctenocephalides felis(ネコノ
ミ)、Ctenocephalides canis
(イヌノミ)、Ceratophyllusspp.
(トゲノミの一種)、Pulex spp.(ヒトノミ
の一種)などの隠翅目(Siphonaptera)害
虫;Scorpio maurus、Latrodec
tus mactans、Chiracanthium
spp.(コマチグモの一種)などの蛛形綱(Ara
chnida)害虫;Pectinophora gossip
iella (Limegrass beetle), Lithocolle
tis blankcardella (a kind of hosoga),
Plutella xylostella (conaga),
Malacosoma neustria (Obikareja), Euprotis subflava (Dokuga), Lymantria dispar (Gypsy moth), Bucculatrixpyrivorella
(Nasitibiga), Phyllocnistis cit
rella, Citrus agrotis, Agrotis s
pp. (A kind of Kaburayaga), Euxoa spp.
(A kind of noctuids), Earias insulana (a kind of waterlinga), Heliothis spp. (A kind of beetle), Spodoptera exigu
a. litura (Spodoptera litura), Spodoptera spp. (A kind of armyworm), Mamestra brassicae (armyworm), Trichoplusia ni (a kind of armyworm), Carpocapsa pomonella
(Codlinga), Pieris spp. (A kind of cabbage butterfly), Chilo spp. (A kind of potato), Pyrausta nubilalis (a kind of potato), Ephessia kuehniella
(Sujiko nomadameiga), Galleria mel
lonella (Honey moth), Tineolabis
selliella (koiga), Tenea tran
slucens (Iga), Homona magnan
ima (chahamaki), Tortrixviridan
a (Lepidoptera)
ra) Pests: Anobium punctatum (a kind of beetle), Rhizopertha domi
Nicca, Acanthosce
rides obectus (Pink beetle), Agelastica alni (a kind of leaf beetle), Leptinotarsa decemli
neata (Colorado potato beetle), Phaedon co
chleariae (a kind of beetle), Diabrot
ica spp. (A kind of corn rootworm), Ps
ylliodes angusticollis (Eggplant flea beetle), Phyllotretastriola
ta (Eurasian flea beetle), Epilachna sp
p. (A kind of ladybird)
iaspp. (A kind of beetle), Oryzaeph
ilus surinamensis, Anthonomus spp. (A kind of weevil), Sitophilus spp. (A kind of weevil), Otiohynchus sulc
atus, Cosmopo
lites sordidus, ceuthorhyncidius albos
uturalis (hyper weevil), Hypera
postica (alfalfa weevil), D
ermestes spp. A kind of cutlet bug),
Trogoderma spp. (A kind of beetle beetle), Attagenus unicolor
(Himekatsuobushimushi), Lyctus dentat
um (Alageniferus bark beetle), L. planico
llis (American Flycatcher beetle), L. sine
nsis (Keyaki Hirataki Beetle), L. n. linea
ris (Narahira bark beetle), L. brunneu
s (Hirata bark beetle); africanus (African fly bark beetle) and other leaf beetle families (L
yctridae), Meligethes aene
us (a kind of poppy), Ptinusspp. (A kind of leopard beetle), Gibbium psyllo
ides (Triple leopard beetle), Triboliu
m spp. (A kind of succulent), Teneb
rio molitor (Acalycium beetle), Agriotes spp. (A kind of Munaboshi beetle), Melolontha mololoth
a (a kind of stag beetle), genus Xyleborus, S
bark beetles of the genus coloplatypus (S
(corytidae), genus Monochamus, Hy
genus lotrupes, Hesperophanus,
Chlorophorus, Palaeocalli
genus, Semanotus, Purpuric
Enumus, Stromium and the like, Cerambycidae, Crossotar
Platypoidae, such as genus sus and Platypus, Dinoderus
Genus, Botrychus, Sinoderus, etc.
Genus Ernobius, genus Anobium, Xyleti
genus nus, genus Xestobium, Ptilinus
Genus, Nicobium, Ptilineurus, etc., Coleoptera (Anobiidae), Coleoptera (Bupresidae), etc., Coleoptera (Coleo)
ptera) pest; Diprion spp. (A kind of black-spotted wasp), Hoplocampa spp.
(A kind of bee), Lasius spp. (A kind of black ant), Formica japonica (Black ant), Vespa spp. Hymenoptera (Hymenop) such as the wasp family (Siricidae) of the genus Urocerus, Sirex, etc.
tera) pests; Aedes spp. (A kind of sea lion), Anopheles spp. (A kind of anopheles), Culex spp. (A kind of Culex), Dro
sophila melanogaster (a kind of Drosophila melanogaster), Musca domestici
ca (housefly), Fannia spp. (A kind of Musca domestica), Calliphora spp. (A kind of blowfly), Lucilia spp. (A kind of fly), Chrysomya spp. (A kind of lobster), Cuterebra spp. , Gastr
ophilusspp. (A kind of horsefly), Storm
oxys spp. (A kind of flies), Oestru
s spp. (A kind of sheep fly), Hypoderm
a spp. (A kind of bullflies), Tabanus s
pp. (A kind of flies), Biohortullan
us (a kind of flies), Pegomyia hyosc
yami (a kind of fly), Ceratitis c
apitata (Diptera), Dacus
dorsalis (Fruit fruit fly), Tipula
paludosa (a kind of gagbo), Simuliu
m spp. (A kind of blackflies), Eusimulium
spp. , Phlebotomus spp. (A kind of sandfly), Culicoides spp.
(A kind of Nukaka), Chrysops spp. (A kind of black fly), Haematopota spp.
(A kind of flies), Braula spp. (A kind of honeybee fly), Morellia spp.
(A kind of fly), Glossina spp. (A kind of tsetse fly), Wohlfahrtia sp
p. , Sarcophaga spp. (A kind of flies), Lipoptena spp. (A kind of lice) and Melophagus spp. (A kind of lice), Muscina spp. (Diptera) pests such as (a house fly); Xenop
sylla cheopis,
Ctenocephalides felis (cat flea), Ctenocephalides canis
(Dog flea), Ceratophyllus spp.
(A kind of spiny flea), Pulex spp. (One of the human fleas), such as Siphonaptera pests; Scorpio maurus, Latrodec
tus mactans, Chiracantium
spp. (Ara)
chnida) pests;
【0013】Otodectes spp.(ミミヒゼ
ンダニの一種)、Acarus siro(アシブトコ
ナダニ)Argas spp.(ヒメダニの一種)、O
rnithodoros spp.(カズキダニの一
種)、Ornithonyssus spp.(イエダ
ニの一種)、Dermanyssus spp.(ワク
モの一種)、Eriophyes spp.(フシダニ
の一種)、Haemaphyxalis longic
ornis(フタトゲチマダニ)、Boophilus
microplus(オウシマダニ)、Rhipic
ephalus spp.(コイタマダニの一種)、C
helacaropsis moorei(ミナミツメ
ダニ)、Dermatophagoides spp.
(ヒョウヒダニの一種)、Hyalomma spp.
(イボマダニの一種)、Ixodesovatus(ヤ
マトマダニ)、Ixodes persulcatus
(シュルツェマダニ)、Psoroptes equi
(キュウセンヒゼンダニ)、Chorioptes s
pp.(ショクヒヒゼンダニの一種)、Sarcopt
es spp.(ヒゼンダニの一種)、Tarsone
mus spp.(ホコリダニの一種)、Bryobi
a praetiosa(クローバハダニ)、Pano
nychus spp.(ミカンハダニの一種)、Te
tranychus spp.(ナミハダニの一種)、
Dermacentor spp.(カクマダニの一
種)、Haemaphysalis spp.(チマダ
ニの一種)、Raillietia spp.、Pne
umonyssus spp.(サルハイダニの一
種)、Sternostorma spp.、Acar
apisspp.(ミツバチダニの一種)、Cheyl
etiella spp.(ツメダニの一種)、Myo
bia spp.(ケモチダニの一種)、Psorer
gatesspp.(ヒツジツメダニの一種)、Dem
odex spp.(ニキビダニの一種)、Tromb
icula spp.(ツツガムシの一種)、List
rophorus spp.(ズツキダニの一種)、T
yrophagus spp.(ケナガコナダニの一
種)、Sarcoptes spp.(イヌセンコウヒ
ゼンダニの一種)、Notoedres spp.(ネ
コショウセンコウヒゼンダニの一種)、Cytodid
es spp.(フエダニの一種)、Laminosi
optes spp.などのダニ目(Acarina)
害虫;Pratylenchus spp.(ネグサレ
センチュウの類)、Grobodera spp.、H
eterodera spp.(シストセンチュウの
類)、Meloidogyne spp.(ネコブセン
チュウの類)、Aphelenchoides sp
p.(シンガレセンチュウの類)、Notylench
us spp.(メセンチュウの類)、Bursaph
elenchus lignicolus(マツノザイ
センチュウ)などの植物寄生性線虫の害虫等が挙げられ
る。さらに本発明化合物は既存の殺虫、殺ダニ、殺線虫
剤に対し、抵抗性の発達した害虫にも有効である。Otodictes spp. (A kind of mites), Acarus siro (Acari: Acarina) Argas spp. (A kind of ticks), O
rnithodoros spp. (A kind of mites), Ornithonyssus spp. (A kind of house dust mite), Dermanyssus spp. (A kind of mites), Eriophys spp. (A kind of mites), Haemaphyxalis longic
ornis (Tickle tick), Boophilus
microplus, Rhipic
ephalus spp. (A kind of red tick), C
helicaropsis moorei (Small mites), Dermatophagoides spp.
(A kind of Dermatophagoides mite), Hyalomma spp.
(A kind of Ixodid tick), Ixodesovatus (Yamato-mite), Ixodes persulcatus
(Schulze tick), Psoroptes equi
(Kyusen mite), Chorioptes s
pp. (A kind of red mite), Sarcopt
es spp. (Scarlet mite), Tarsone
mus spp. (A kind of dust mite), Bryobi
a Praetiosa (Clover spider mite), Pano
nychus spp. (A kind of Citrus spider mite), Te
tranychus spp. (A kind of spider mite),
Dermacentor spp. (A kind of Oxodid tick), Haemaphysalis spp. (A kind of tick), Railietia spp. , Pne
umonyssus spp. (A kind of Salmonid mite), Sternostoma spp. , Acar
apisspp. (A kind of bee mite), Cheyl
etiella spp. (A kind of claw mite), Myo
bia spp. (A kind of mite mite), Psorer
gatespp. (A kind of sheep mite), Dem
odex spp. (A kind of acne mites), Tromb
icula spp. (A kind of chiggers), List
rophorus spp. (A kind of woodpecker), T
yrophagus spp. (A kind of Acarina mites), Sarcoptes spp. (A kind of red mite), Notoedres spp. (A kind of cat mite), Cytodid
es spp. (A kind of dust mite), Laminoshi
optes spp. Acarina
Pests; Pratylenchus spp. (Negusa nematode species), Grobodera spp. , H
eterodera spp. (Cyst nematodes), Meloidogyne spp. (A kind of root-knot nematode), Aphelenchoides sp
p. (Singare nematodes), Notylench
us spp. (Messiah species), Bursap
Pests of plant parasitic nematodes, such as elenchus lignicolus (pine wood nematode). Furthermore, the compounds of the present invention are also effective against pests that have developed resistance to existing insecticides, mites and nematicides.
【0014】本発明化合物を殺虫、殺ダニ、殺線虫剤の
有効成分として用いる場合は、本発明化合物または本発
明化合物の塩{無機酸(塩酸、硫酸等)または有機酸
(p−トルエンスルホン酸等)との農薬学的に許容され
る塩}を、他の何らの成分も加えず、そのまま使用して
もよいが、通常は、固体担体、液体担体、ガス状担体、
餌等と混合するか、あるいは多孔セラミックス板や不織
布等の基材に含浸し、必要あれば界面活性剤、その他の
製剤用補助剤を添加して、油剤、乳剤、水和剤、フロア
ブル剤、粒剤、粉剤、エアゾ−ル、煙霧剤(フォッギン
グ等)、加熱蒸散剤、燻煙剤、毒餌、防ダニシ−ト、樹
脂製剤等に製剤して使用する。これらの製剤には、有効
成分として本発明化合物を重量比で通常0.01%〜9
5%含有する。When the compound of the present invention is used as an active ingredient of an insecticide, acaricide, or nematicide, the compound of the present invention or a salt of the compound of the present invention—an inorganic acid (such as hydrochloric acid or sulfuric acid) or an organic acid (p-toluene sulfone) An acid or the like) and a pharmaceutically acceptable salt thereof may be used as it is without adding any other components, but usually, a solid carrier, a liquid carrier, a gaseous carrier,
Mix with feed, etc., or impregnate into a substrate such as a porous ceramics plate or a non-woven fabric, and add a surfactant or other formulation auxiliary agent, if necessary, to make oils, emulsions, wettable powders, flowables, It is used in the form of granules, powders, aerosols, aerosols (eg, fogging), heat transpiration agents, smokers, poison baits, mites, resin formulations, etc. In these preparations, the compound of the present invention is usually contained in an amount of 0.01% to 9% by weight as an active ingredient.
Contains 5%.
【0015】かかる製剤化の際に用いられる固体担体と
しては、例えば粘土類(カオリンクレー、珪藻土、合成
含水酸化珪素、ベントナイト、フバサミクレー、酸性白
土等)、タルク類、セラミック、その他の無機鉱物(セ
リサイト、石英、硫黄、活性炭、炭酸カルシウム、水和
シリカ等)、化学肥料(硫安、燐安、硝安、尿素、塩安
等)等の微粉末あるいは粒状物等があげられ、液体担体
としては、例えば水、アルコ−ル類(メタノール、エタ
ノール等)、ケトン類(アセトン、メチルエチルケトン
等)、芳香族炭化水素類(ベンゼン、トルエン、キシレ
ン、エチルベンゼン、メチルナフタレン等)、脂肪族炭
化水素類(ヘキサン、シクロヘキサン、灯油、軽油
等)、エステル類(酢酸エチル、酢酸ブチル等)、ニト
リル類(アセトニトリル、イソブチロニトリル等)、エ
ーテル類(ジイソプロピルエ−テル、ジオキサン等)、
酸アミド類(N、N−ジメチルホルムアミド、N、N−
ジメチルアセトアミド等)、ハロゲン化炭化水素類(ジ
クロロメタン、トリクロロエタン、四塩化炭素等)、ジ
メチルスルホキシド、大豆油、綿実油等の植物油等があ
げられ、ガス状担体、すなわち噴射剤としては、例えば
フロンガス、ブタンガス、LPG(液化石油ガス)、ジ
メチルエ−テル、炭酸ガス等があげられる。[0015] Examples of the solid carrier used in the formulation include clays (kaolin clay, diatomaceous earth, synthetic hydrous silicon oxide, bentonite, fubasami clay, acid clay, etc.), talcs, ceramics, and other inorganic minerals (cellulose). Fine powder or granular materials such as cite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica, etc., and chemical fertilizers (ammonium sulfate, phosphorous ammonium, nitrate, urea, salt ammonium, etc.). For example, water, alcohols (such as methanol and ethanol), ketones (such as acetone and methyl ethyl ketone), aromatic hydrocarbons (such as benzene, toluene, xylene, ethylbenzene and methylnaphthalene), and aliphatic hydrocarbons (such as hexane and ethanol) Cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile , Isobutyronitrile), ethers (diisopropyl e - ether, dioxane),
Acid amides (N, N-dimethylformamide, N, N-
Dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), vegetable oils such as dimethylsulfoxide, soybean oil, cottonseed oil and the like. , LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide and the like.
【0016】毒餌の基材としては、例えば穀物粉、植物
油、糖、結晶セルロ−ス等の餌成分、ジブチルヒドロキ
シトルエン、ノルジヒドログアイアレチック酸等の酸化
防止剤、デヒドロ酢酸等の保存料、トウガラシ末等の誤
食防止剤、チ−ズ香料、タマネギ香料等の誘引性香料等
があげられる。界面活性剤としては、例えばアルキル硫
酸エステル塩、アルキルスルホン酸塩、アルキルアリ−
ルスルホン酸塩、アルキルアリ−ルエ−テル類およびそ
のポリオキシエチレン化物、ポリエチレングリコ−ルエ
−テル類、多価アルコ−ルエステル類、糖アルコ−ル誘
導体等があげられる。固着剤や分散剤等の製剤用補助剤
としては、例えばカゼイン、ゼラチン、多糖類(でんぷ
ん粉、アラビアガム、セルロ−ス誘導体、アルギン酸
等)、リグニン誘導体、ベントナイト、糖類、合成水溶
性高分子(ポリビニルアルコ−ル、ポリビニルピロリド
ン、ポリアクリル酸類等)等があげられ、安定剤として
は、例えばPAP(酸性リン酸イソプロピル)、BHT
(2、6−ジ−tert−ブチル−4−メチルフェノ−
ル)、BHA(2−tert−ブチル−4−メトキシフ
ェノ−ルと3−tert−ブチル−4−メトキシフェノ
−ルとの混合物)、植物油、鉱物油、界面活性剤、脂肪
酸またはそのエステル等があげられる。Examples of the bait bait include bait ingredients such as cereal flour, vegetable oil, sugar and crystalline cellulose, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, and preservatives such as dehydroacetic acid. Examples thereof include an ingestion inhibitor such as pepper powder, an attractive flavor such as a cheese flavor and an onion flavor. Examples of the surfactant include an alkyl sulfate, an alkyl sulfonate, and an alkyl allylate.
Sulfonates, alkyl aryl ethers and polyoxyethylenates thereof, polyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives and the like. Examples of auxiliary agents for preparations such as fixing agents and dispersants include casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, saccharides, synthetic water-soluble polymers ( Polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), and examples of the stabilizer include PAP (acidic isopropyl phosphate) and BHT.
(2,6-di-tert-butyl-4-methylpheno-
), BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil, surfactant, fatty acid or ester thereof and the like. can give.
【0017】本発明化合物を農業用殺虫、殺ダニ、殺線
虫剤として用いる場合、その施用量は10ア−ルあたり
通常0.1〜100gであり、乳剤、水和剤、フロアブ
ル剤等を水で希釈して用いる場合は、その施用濃度は通
常1〜10000ppmであり、粒剤、粉剤等は何ら希
釈することなく製剤のままで施用する。また、防疫用殺
虫、殺ダニ、殺線虫剤として用いる場合には、乳剤、水
和剤、フロアブル剤等は、通常、水で0.1ppm〜5
00ppmに希釈して施用し、油剤、エアゾ−ル、煙霧
剤、毒餌、防ダニシ−ト等についてはそのまま施用す
る。これらの施用量、施用濃度は、いすれも製剤の種
類、施用時期、施用場所、施用方法、害虫の種類、被害
程度等の状況によって異なり、上記の範囲にかかわるこ
となく増減することができる。When the compound of the present invention is used as an insecticide, acaricide or nematicide for agriculture, the application rate is usually 0.1 to 100 g per 10 ares, and emulsions, wettable powders, flowables and the like are used. When diluted with water, the application concentration is usually 1 to 10000 ppm, and granules, powders, and the like are applied as they are without dilution. When used as an insecticide, miticide or nematicide for epidemic prevention, the emulsion, wettable powder, flowable and the like are usually 0.1 ppm to 5 ppm in water.
It is applied after being diluted to 00 ppm, and oils, aerosols, aerosols, poison baits, anti-mite sheets and the like are applied as they are. These application rates and application concentrations differ depending on the type of preparation, application time, application place, application method, type of pest, degree of damage, and the like, and can be increased or decreased without being affected by the above range.
【0018】本発明化合物は、哺乳類に対する安全性が
高いことから、特に動物外部寄生虫の防除に適してい
る。本発明化合物をウシ、ブタ等の家畜類、イヌ、ネコ
等のペット等の動物外部寄生虫防除を目的として、殺
虫、殺ダニ剤として使用する場合は、本発明化合物また
は本発明化合物の塩を、獣医学的に公知の方法で使用す
る。例えば全身的抑制(systemic contr
ol)を目的とする場合では、錠剤、カプセル、浸漬
液、ボリ(boli)、飼料混入、坐薬、注射(筋肉
内、皮下、静脈内、腹腔内等)等の方法を、非全身的抑
制(non− systemic control)を
目的とする場合では、油性または水性液剤を噴霧、注ぎ
かけ(pour−on)、滴下(spot−on)等の
方法、及び樹脂製剤を首輪、耳札等の適当な形状に成形
した物を用いることにより使用する。本発明化合物は、
通常、宿主動物1kgに対して、本発明化合物として
0.01〜100mgを施用する。The compounds of the present invention are particularly suitable for controlling animal ectoparasites because of their high safety for mammals. When the compound of the present invention is used as an insecticide or acaricide for the purpose of controlling ectoparasites of animals such as livestock such as cattle and pigs, pets such as dogs and cats, the compound of the present invention or a salt of the compound of the present invention is used. Used in a veterinary manner. For example, systemic control (systemic controller)
ol), a method such as tablet, capsule, immersion liquid, boli, feed mixing, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) is used for non-systemic suppression ( For the purpose of non-systemic control, methods such as spraying, pouring (pour-on), and dropping (spot-on) an oily or aqueous solution, and forming a resin formulation into a suitable shape such as a collar or ear tag It is used by using a molded article. The compound of the present invention
Usually, 0.01 to 100 mg of the compound of the present invention is applied to 1 kg of a host animal.
【0019】また、本発明化合物は、他の殺虫剤、殺線
虫剤、殺ダニ剤、殺菌剤、除草剤、植物生長調節剤、共
力剤、肥料、土壌改良剤、動物用飼料等と混用または併
用することもできる。かかる殺虫剤、殺線虫剤、殺ダニ
剤の有効成分としては、例えばフェニトロチオン[O、
O−ジメチル O−(3−メチル−4−ニトロフェニ
ル)ホスホロチオエ−ト]、フェンチオン[O、O−ジ
メチル O−(3−メチル−4−(メチルチオ)フェニ
ル)ホスホロチオエ−ト]、ダイアジノン[O、O−ジ
エチル−O−2−イソプロピル−6−メチルピリミジン
−4−イルホスホロチオエ−ト]、クロルピリホス
[O、O−ジエチル−O−3、5、6−トリクロロ−2
−ピリジルホスホロチオエ−ト]、アセフェ−ト[O、
S−ジメチルアセチルホスホラミドチオエ−ト]、メチ
ダチオン[S−2、3−ジヒドロ−5−メトキシ−2−
オキソ−1、3、4−チアジアゾ−ル−3−イルメチル
O、O−ジメテルホスホロジチオエ−ト]、ジスルホ
トン[O、O−ジエチル S−2−エチルチオエチルホ
スホロジチオエ−ト]、DDVP[2、2−ジクロロビ
ニルジメチルホスフェ−ト]、スルプロホス[O−エチ
ル O−4−(メチルチオ)フェニル S−プロピルホ
スホロジチオエ−ト]、シアノホス[O−4−シアノフ
ェニル O、O−ジメチルホスホロチオエ−ト]、ジオ
キサベンゾホス[2−メトキシ−4H−l、3、2−ベ
ンゾジオキサホスホリン−2−スルフィド]、ジメトエ
−ト[O、O−ジメチル−S−(N−メチルカルバモイ
ルメチル)ジチオホスフェ−ト]、フェントエ−ト[エ
チル 2−ジメトキシホスフィノチオイルチオ(フェニ
ル)アセテ−ト]、マラチオン[ジエチル(ジメトキシ
ホスフィノチオイルチオ)サクシネ−ト]、トリクロル
ホン[ジメチル 2、2、2−トリクロロ−1−ヒドロ
キシエチルホスホネ−ト]、アジンホスメチル[S−
3、4−ジヒドロ−4−オキソ−1、2、3−ベンゾト
リアジン−3−イルメチル O、O−ジメチルホスホロ
ジチオエ−ト]、モノクロトホス[ジメチル(E)−1
−メチル−2−(メチルカルバモイル)ビニルホスフエ
−ト]、エチオン[O、O、O’、O’−テトラエチル
S、S’−メチレンビス(ホスホロジチオエ−ト)]
等の有機リン系化合物、BPMC(2−sec−ブチル
フェニル メチルカ−バメ−ト]、ベンフラカルブ[エ
チル N−[2、3−ジヒドロ−2、2−ジメチルベン
ゾフラン−7−イルオキシカルボニル(メチル)アミノ
チオ]−N−イソプロピル−β−アラニネ−ト]、プロ
ポキスル[2−イソプロポキシフェニル N−メチルカ
−バメ−ト]、カルボスルファン[2、3−ジヒドロ−
2、2−ジメチル−7−べンゾ[b]フラニル N−ジ
ブチルアミノチオ−N−メチルカ−バメ−ト]、カルバ
リル[1−ナフチル−N−メチルカ−バメ−ト]、メソ
ミル[S−メチル−N−[(メチルカルバモイル)オキ
シ]チオアセトイミデ−ト]、エチオフェンカルブ[2
−(エチルチオメチル)フェニルメチルカ−バメ−
ト]、アルジカルブ[2−メチル−2−(メチルチオ)
プロピオンアルデヒド O−メチルカルバモイルオキシ
ム]、オキサミル[N、N−ジメチル−2−メチルカル
バモイルオキシイミノ−2−(メチルチオ)アセタミ
ド]、フェノチオカルブ[S−(4−フェノキシブチ
ル)−N、N−ジメチルチオカ−バメ−ト]等のカ−バ
メ−ト系化合物、The compound of the present invention can be used with other insecticides, nematicides, acaricides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners, animal feeds, etc. They can be mixed or used in combination. Examples of the active ingredient of such insecticides, nematicides, and miticides include, for example, fenitrothion [O,
O-dimethyl O- (3-methyl-4-nitrophenyl) phosphorothioate], phenthione [O, O-dimethyl O- (3-methyl-4- (methylthio) phenyl) phosphorothioate], diazinon [O, O-diethyl-O-2-isopropyl-6-methylpyrimidin-4-yl phosphorothioate], chloropyrifos [O, O-diethyl-O-3,5,6-trichloro-2
-Pyridyl phosphorothioate], acephate [O,
S-dimethylacetyl phosphoramidothioate], methidathion [S-2,3-dihydro-5-methoxy-2-
Oxo-1,3,4-thiadiazol-3-ylmethyl O, O-dimeterphosphorodithioate], disulfoton [O, O-diethyl S-2-ethylthioethylphosphorodithioate] , DDVP [2,2-dichlorovinyl dimethyl phosphate], sulphophos [O-ethyl O-4- (methylthio) phenyl S-propyl phosphorodithioate], cyanophos [O-4-cyanophenyl O, O-dimethyl phosphorothioate], dioxabenzophos [2-methoxy-4H-1, 3,2-benzodioxaphosphorin-2-sulfide], dimethoate [O, O-dimethyl-S- (N-methylcarbamoylmethyl) dithiophosphate], fentoate [ethyl 2-dimethoxyphosphinothioylthio (phenyl) acetate], malachi Emissions [diethyl (dimethoxy phosphino Chi oil thio) Sakushine - DOO], trichlorfon [dimethyl 2,2,2-trichloro-1-hydroxyethyl phosphate bone - DOO], azinphos-methyl [S-
3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethyl O, O-dimethylphosphorodithioate], monocrotophos [dimethyl (E) -1
-Methyl-2- (methylcarbamoyl) vinyl phosphate], ethion [O, O, O ', O'-tetraethyl S, S'-methylenebis (phosphorodithioate)]
BPMC (2-sec-butylphenyl methylcarbamate), benfracarb [ethyl N- [2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl (methyl) aminothio] ] -N-isopropyl-β-alaninate], propoxur [2-isopropoxyphenyl N-methylcarbamate], carbosulfan [2,3-dihydro-
2,2-dimethyl-7-benzo [b] furanyl N-dibutylaminothio-N-methylcarbamate], carbaryl [1-naphthyl-N-methylcarbamate], mesomil [S-methyl] -N-[(methylcarbamoyl) oxy] thioacetimidate], ethiophenecarb [2
-(Ethylthiomethyl) phenylmethylcarbamoy
G], aldicarb [2-methyl-2- (methylthio)
Propionaldehyde O-methylcarbamoyloxime], oxamyl [N, N-dimethyl-2-methylcarbamoyloxyimino-2- (methylthio) acetamide], phenothiocarb [S- (4-phenoxybutyl) -N, N-dimethylthiocarbame -G) -based carbamate compounds;
【0020】エトフェンプロックス[2−(4−エトキ
シフェニル)−2−メチルプロピル−3−フェノキシベ
ンジルエ−テル]、フェンバレレ−ト[(RS)−α−
シアノ−3−フェノキシベンジル (RS)−2−(4
−クロロフェニル)−3−メチルブチレ−ト]、エスフ
ェンバレレ−ト[(S)−α−シアノ−3−フェノキシ
ベンジル (S)−2−(4−クロロフェニル)−3−
メチルブチレ−ト]、フェンプロパトリン[(RS)−
α−シアノ−3−フェノキシベンジル 2、2、3、3
−テトラメチルシクロプロパンカルボキシレ−ト]、シ
ペルメトリン[(RS)−α−シアノ−3−フェノキシ
ベンジル (1RS)−シス、トランス−3−(2、2
−ジクロロビニル)−2、2−ジメチルシクロプロパン
カルボキシレ−ト]、ペルメトリン[3−フェノキシベ
ンジル (1RS)−シス、トランス−3−(2、2−
ジクロロビニル)−2、2−ジメチルシクロプロパンカ
ルボキシレ−ト]、シハロトリン[(RS)−α−シア
ノ−3−フェノキシベンジル(Z)−(1RS)−ci
s−3−(2−クロロ−3、3、3−トリフルオロプロ
プ−1−エニル)−2、2−ジメチルシクロプロパンカ
ルボキシレ−ト]、デルタメトリン[(S)−α−シア
ノ−3−フェノキシベンジル (1R)−シス−3−
(2、2−ジブロモビニル)−2、2−ジメチルシクロ
プロパンカルボキシレ−ト]、シクロプロトリン[(R
S)−α−シアノ−3−フェノキシベンジル (RS)
−2、2−ジクロロ−1−(4−エトキシフェニル)シ
クロプロパンカルボキシレ−ト]、フルバリネ−ト(α
−シアノ−3−フェノキシベンジル N−(2−クロロ
−α、α、α−トリフルオロ−p−トリル)−D−バリ
ネ−ト)、ビフェンスリン(2−メチルビフェニル−3
−イルメチル)(Z)−(1RS)−cis−3−(2
−クロロ−3、3、3−トリフルオロ−1−プロペニ
ル)−2、2−ジメチルシクロプロパンカルボキシレ−
ト、2−メチル−2−(4−ブロモジフルオロメトキシ
フェニル)プロピル(3−フェノキシベンジル)エ−テ
ル、トラロメトリン[(S)−α−シアノ−3−フェノ
キシベンジル(1R)−シス−3−(1、2、2、2−
テトラブロモエチル)−2、2−ジメチルシクロプロパ
ンカルボキシレ−ト]、シラフルオフェン[4−エトキ
シフェニル{3−(4−フルオロ−3−フェノキシフェ
ニル)プロピル)ジメチルシラン]、d−フェノトリン
[3−フェノキシベンジル (1R−シス、トランス)
−クリサンテマ−ト]、シフェノトリン[(RS)−α
−シアノ−3−フェノキシベンジル (1R−シス、ト
ランス)−クリサンテマ−ト)、d−レスメトリン[5
−ベンジル−3−フリルメチル (1R−シス、トラン
ス)−クリサンテマ−ト]、アクリナスリン[(S)−
α−シアノ−3−フェノキシベンジル (1R−シス
(Z))−(2、2−ジメチル−3−(3−オキソ−3
−(1、1、1、3、3、3−ヘキサフルオロプロピル
オキシ)プロペニル)シクロプロパンカルボキシレ−
ト]、シフルトリン[(RS)−α−シアノ−4−フル
オロ−3−フェノキシベンジル 3−(2、2−ジクロ
ロビニル)−2、2−ジメチルシクロプロパンカルボキ
シレ−ト]、テフルトリン[2、3、5、6−テトラフ
ルオロ−4−メチルベンジル (1RS−シス(Z))
−3−(2−クロロ−3、3、3−トリフルオロプロプ
−1−エニル)−2、2−ジメチルシクロプロパンカル
ボキシレ−ト]、トランスフルスリン[2、3、5、6
−テトラフルオロベンジル (1R−トランス)−3−
(2、2−ジクロロビニル)−2、2−ジメチルシクロ
プロパン力ルボキシレ−ト]、テトラメトリン[3、
4、5、6−テトラヒドロフタルイミドメチル (1R
S)−シス、トランス−クリサンテマ−ト]、アレトリ
ン[(RS)−3−アリル−2−メチル−4−オキソシ
クロペント−2−エニル (1RS)−シス、トランス
−クリサンテマ−ト]、プラレトリン[(S)−2−メ
チル−4−オキソ−3−(2−プロピニル)シクロペン
ト−2−エニル (1R)−シス、トランス−クリサン
テマ−ト]、エンペントリン[(RS)−1−エチニル
−2−メチル−2−ペンテニル (1R)−シス、トラ
ンス−クリサンテマ−ト]、イミプロスリン[2、5−
ジオキソ−3−(プロプ−2−イニル)イミダゾリジン
−1−イルメチル (1R)−シス、トランス−2、2
−ジメチル−3−(2−メチル−1−プロペニル)シク
ロプロパンカルボキシレ−ト]、d−フラメトリン[5
−(2−プロピニル)フルフリル (1R)−シス、ト
ランス−クリサンテマ−ト]、5−(2−プロピニル)
フルフリル 2、2、3、3−テトラメチルシクロプロ
パンカルボキシレ−ト等のピレスロイド化合物、Etofenprox [2- (4-ethoxyphenyl) -2-methylpropyl-3-phenoxybenzyl ether], fenvalerate [(RS) -α-
Cyano-3-phenoxybenzyl (RS) -2- (4
-Chlorophenyl) -3-methylbutyrate], esfenvalerate [(S) -α-cyano-3-phenoxybenzyl (S) -2- (4-chlorophenyl) -3-
Methyl butyrate], fenpropatrin [(RS)-
α-cyano-3-phenoxybenzyl 2,2,3,3
-Tetramethylcyclopropanecarboxylate], cypermethrin [(RS) -α-cyano-3-phenoxybenzyl (1RS) -cis, trans-3- (2,2
-Dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate], permethrin [3-phenoxybenzyl (1RS) -cis, trans-3- (2,2-
Dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate], cyhalothrin [(RS) -α-cyano-3-phenoxybenzyl (Z)-(1RS) -ci
s-3- (2-Chloro-3,3,3-trifluoroprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate], deltamethrin [(S) -α-cyano-3-phenoxy] Benzyl (1R) -cis-3-
(2,2-dibromovinyl) -2,2-dimethylcyclopropanecarboxylate], cycloprothrin [(R
S) -α-Cyano-3-phenoxybenzyl (RS)
-2,2-dichloro-1- (4-ethoxyphenyl) cyclopropanecarboxylate], fluvalinate (α
-Cyano-3-phenoxybenzyl N- (2-chloro-α, α, α-trifluoro-p-tolyl) -D-barynate), bifenthrin (2-methylbiphenyl-3)
-Ylmethyl) (Z)-(1RS) -cis-3- (2
-Chloro-3,3,3-trifluoro-1-propenyl) -2,2-dimethylcyclopropanecarboxyle-
G, 2-methyl-2- (4-bromodifluoromethoxyphenyl) propyl (3-phenoxybenzyl) ether, tralomethrin [(S) -α-cyano-3-phenoxybenzyl (1R) -cis-3- ( 1, 2, 2, 2-
Tetrabromoethyl) -2,2-dimethylcyclopropanecarboxylate], silafluofen [4-ethoxyphenyl {3- (4-fluoro-3-phenoxyphenyl) propyl) dimethylsilane], d-phenothrin [3-phenoxy Benzyl (1R-cis, trans)
-Chrysanthemate], cyphenothrin [(RS) -α
-Cyano-3-phenoxybenzyl (1R-cis, trans) -chrysanthemate), d-resmethrin [5
-Benzyl-3-furylmethyl (1R-cis, trans) -chrysanthemate], acrinasulin [(S)-
α-cyano-3-phenoxybenzyl (1R-cis (Z))-(2,2-dimethyl-3- (3-oxo-3)
-(1,1,1,3,3,3-hexafluoropropyloxy) propenyl) cyclopropanecarboxyle-
G), cyfluthrin [(RS) -α-cyano-4-fluoro-3-phenoxybenzyl 3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate], tefluthrin [2,3 5,6-tetrafluoro-4-methylbenzyl (1RS-cis (Z))
-3- (2-chloro-3,3,3-trifluoroprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate], transfluthrin [2,3,5,6
-Tetrafluorobenzyl (1R-trans) -3-
(2,2-dichlorovinyl) -2,2-dimethylcyclopropane ruboxylate], tetramethrin [3,
4,5,6-tetrahydrophthalimidomethyl (1R
S) -cis, trans-chrysanthemate], aletrin [(RS) -3-allyl-2-methyl-4-oxocyclopent-2-enyl (1RS) -cis, trans-chrysanthemate], praletrin [ (S) -2-methyl-4-oxo-3- (2-propynyl) cyclopent-2-enyl (1R) -cis, trans-chrysanthemate], empentrin [(RS) -1-ethynyl-2-methyl -2-pentenyl (1R) -cis, trans-chrysanthemate], imiprosulin [2,5-
Dioxo-3- (prop-2-ynyl) imidazolidin-1-ylmethyl (1R) -cis, trans-2,2
-Dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylate], d-framethrin [5
-(2-propynyl) furfuryl (1R) -cis, trans-chrysanthemate], 5- (2-propynyl)
Pyrethroid compounds such as furfuryl 2,2,3,3-tetramethylcyclopropanecarboxylate;
【0021】ブプロフェジン(2−tert−ブチルイ
ミノ−3−イソプロピル−5−フェニル−1、3、5−
チアジアジン−4−オン)等のチアジアジン誘導体、ニ
トロイミダゾリジン誘導体、カルタップ(S、S’−
(2−ジメチルアミノトリメチレン)ビス(チオカ−バ
メ−ト)]、チオシクラム[N、N−ジメチル−1、
2、3−トリチアン−5−イルアミン]、ベンスルタッ
プ[S、S’−2−ジメチルアミノトリメチレン ジ
(ベンゼンチオスルフォネ−ト)]等のネライストキシ
ン誘導体、N−シアノ−N’−メチル−N’−(6−ク
ロロ−3−ピリジルメチル)アセトアミジン等のN−シ
アノアミジン誘導体、エンドスルファン[6、7、8.
9、10、10−ヘキサクロロ−1、5、5a、6、
9、9a−ヘキサヒドロ−6、9−メタノ−2、4、3
−ベンゾジオキサチエピンオキサイド]、gamma−
BHC(1、2、3、4、5、6−ヘキサクロロシクロ
ヘキサン]、1、1−ビス(クロロフェニル)−2、
2、2−トリクロロエタノ−ル等の塩素化炭化水素化合
物、クロルフルアズロン[1−(3、5−ジクロロ−4
−(3−クロロ−5−トリフルオロメチルピリジン−2
−イルオキシ)フェニル)−3−(2、6−ジフルオロ
ベンゾイル)ウレア]、テフルベンズロン[1−(3、
5−ジクロロ−2、4−ジフルオロフェニル)−3−
(2、6−ジフルオロベンゾイル)ウレア]、フルフェ
ノクスロン[[1−(4−(2−クロロ−4−トリフルオ
ロメチルフェノキシ)−2−フルオロフェニル]−3−
(2、6−ジフルオロベンゾイル)ウレア]等のベンゾ
イルフェニルウレア系化合物、アミトラズ[N、N’
[(メチルイミノ)ジメチリジン]ジ−2、4−キシリ
ジン]、クロルジメホルム[N’−(4−クロロ−2−
メテルフェニル)−N、N−ジメチルメタニミダミド]
等のホルムアミジン誘導体、ジアフェンチウロン[N−
(2、6−ジイソプロピル−4−フェノキシフェニル)
−N’−tert−ブチルカルボジイミド]等チオ尿素
誘導体、フェニルピラゾ−ル系化合物、メトキサジアゾ
ン[5−メトキシ−3−(2−メトキシフェニル)−
1、3、4−オキサジアゾ−ル−2−(3H)−オ
ン]、ブロモプロピレ−ト[イソプロピル 4、4’−
ジブロモベンジレ−ト]、テトラジホン[4−クロロフ
ェニル 2、4、5−トリクロロフェニルスルホン]、
キノメテオネ−ト[S、S−6−メチルキノキサリン−
2、3−ジイルジチオカルボネ−ト]、プロパルギット
[2−(4−tert−ブチルフェノキシ)シクロヘキ
シル プロピ−2−イル スルファイト]、フェンブタ
ティン オキシド[ビス[トリス(2−メチル−2−フ
ェニルプロピル)ティン]オキシド]、ヘキシチアゾク
ス[(4RS、5RS)−5−(4−クロロフェニル)
−N−クロロヘキシル−4−メテル−2−オキソ−1、
3−チアゾリジン−3−カルボキサミド]、クロフェン
テジン[3、6−ビス(2−クロロフェニル)−1、
2、4、5−テトラジン]、ピリダベン[2−tert
−ブチル−5−(4−tert−ブチルベンジルチオ)
−4−クロロピリダジン−3(2H)−オン]、フェン
ピロキシメ−ト[tert−ブチル(E)−4−
[(1、3−ジメテル−5−フェノキシピラゾ−ル−4
−イル)メチレンアミノオキシメチル]ベンゾエ−
ト]、デブフェンピラド[N−4−tert−ブチルベ
ンジル)−4−クロロ−3−エチル−1−メチル−5−
ピラゾ−ルカルボキサミド]、ポリナクチンコンプレッ
クス[テトラナクチン、ジナクチン、トリナクチン]、
ピリミジフェン[5−クロロ−N−[2−{4−(2−
エトキシエチル)−2、3−ジメチルフェノキシ)エチ
ルコ−6−エチルピリミジン−4−アミン、ミルベメク
テン、アバメクチン、イバ−メクチン、アザジラクチン
[AZAD]等があげられる。Buprofezin (2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-
Thiadiazine derivatives such as thiadiazin-4-one), nitroimidazolidine derivatives, cartap (S, S'-)
(2-dimethylaminotrimethylene) bis (thiocarbamate)], thiocyclam [N, N-dimethyl-1,
Neraistoxin derivatives such as 2,3-trithian-5-ylamine] and bensultap [S, S'-2-dimethylaminotrimethylene di (benzenethiosulfonate)], N-cyano-N'-methyl N-cyanoamidine derivatives such as -N '-(6-chloro-3-pyridylmethyl) acetamidine; endosulfan [6,7,8.
9,10,10-hexachloro-1,5,5a, 6,
9,9a-Hexahydro-6,9-methano-2,4,3
-Benzodioxathiepine oxide], gamma-
BHC (1, 2, 3, 4, 5, 6-hexachlorocyclohexane), 1,1-bis (chlorophenyl) -2,
Chlorinated hydrocarbon compounds such as 2,2-trichloroethanol and chlorofluazurone [1- (3,5-dichloro-4)
-(3-chloro-5-trifluoromethylpyridine-2
-Yloxy) phenyl) -3- (2,6-difluorobenzoyl) urea], teflubenzuron [1- (3,
5-dichloro-2,4-difluorophenyl) -3-
(2,6-difluorobenzoyl) urea], flufenoxuron [[1- (4- (2-chloro-4-trifluoromethylphenoxy) -2-fluorophenyl] -3-
(2,6-difluorobenzoyl) urea] and other benzoylphenylurea-based compounds, amitraz [N, N ′
[(Methylimino) dimethylidin] di-2,4-xylysine], chlorodimform [N ′-(4-chloro-2-
Meterphenyl) -N, N-dimethylmethanimidamide]
Formamidine derivatives, diafenthiuron [N-
(2,6-diisopropyl-4-phenoxyphenyl)
Thiourea derivatives such as -N'-tert-butylcarbodiimide], phenylpyrazole compounds, methoxadiazone [5-methoxy-3- (2-methoxyphenyl)-
1,3,4-oxadiazol-2- (3H) -one], bromopropylate [isopropyl 4,4′-
Dibromobenzylate], tetradiphone [4-chlorophenyl 2,4,5-trichlorophenyl sulfone],
Quinometeone [S, S-6-methylquinoxaline-
2,3-diyldithiocarbonate], propargite [2- (4-tert-butylphenoxy) cyclohexylprop-2-yl sulfite], fenbutatin oxide [bis [tris (2-methyl-2-phenylpropionate)] Ru) tin] oxide], hexthiazox [(4RS, 5RS) -5- (4-chlorophenyl)
-N-chlorohexyl-4-meter-2-oxo-1,
3-thiazolidine-3-carboxamide], clofentezine [3,6-bis (2-chlorophenyl) -1,
2,4,5-tetrazine], pyridaben [2-tert]
-Butyl-5- (4-tert-butylbenzylthio)
-4-chloropyridazin-3 (2H) -one], fenpyroximate [tert-butyl (E) -4-
[(1,3-dimeter-5-phenoxypyrazol-4)
-Yl) methyleneaminooxymethyl] benzoe-
G], debufenpyrado [N-4-tert-butylbenzyl) -4-chloro-3-ethyl-1-methyl-5-
Pyrazole carboxamide], polynactin complex [tetranactin, dinactin, trinactin],
Pyrimidiphene [5-chloro-N- [2- {4- (2-
Ethoxyethyl) -2,3-dimethylphenoxy) ethylco-6-ethylpyrimidin-4-amine, milbemectene, abamectin, iva-mectin, azadirachtin [AZAD] and the like.
【0022】[0022]
【実施例】以下、本発明を製造例、製剤例および試験例
等によりさらに詳しく説明するが、本発明はこれらの例
に限定されるものでない。まず、本発明化合物の製造例
および、製造中間体の参考製造例を示す。 製造例1 3−ジクロロフルオロメチルスルフェニル−1−(2,
6−ジクロロ−4−トリフルオロメチルフェニル)−5
−(N−エトキシカルボニルアミノ)−1,2,4−ト
リアゾール1.30g(2.60ミリモル)およびテト
ラヒドロフラン13mlの混合物に水素化ナトリウム
(油性、約60%含有)0.140g(3.40ミリモ
ル)を氷冷下で加え、15分間攪拌した。次にクロロメチ
ル エチルエーテル0.320g(3.40ミリモル)
および15−クラウン−5を数滴加え、室温にて15時
間攪拌した。減圧下に溶媒を留去した後、残渣に水を注
加し、酢酸エチルで抽出した。該有機層を飽和食塩水で
洗浄し、無水硫酸マグネシウムで乾燥した。減圧下に濃
縮し、残渣をシリカゲルカラムクロマトグラフィーに付
し、3−ジクロロフルオロメチルスルフェニル−1−
(2,6−ジクロロ−4−トリフルオロメチルフェニ
ル)−5−〔N−エトキシカルボニル−N−(エトキシ
メチル)アミノ〕−1,2,4−トリアゾール〔以下、
本発明化合物1と記す〕1.0gを得た。1 H−NMR(250MHz,CDCl3/TMS):δ
(ppm)=7.75(s,2H),5.09(s,2
H),4.13(q,J=7.1Hz,2H), 3.60
(q,J=7.0Hz,2H), 1.16(t,J=7.
1Hz,3H), 1.08(t,J=7.0Hz,3H)EXAMPLES The present invention will be described in more detail with reference to Production Examples, Formulation Examples, Test Examples, etc., but the present invention is not limited to these Examples. First, Production Examples of the compound of the present invention and Reference Production Examples of production intermediates are shown. Production Example 1 3-dichlorofluoromethylsulfenyl-1- (2,
6-dichloro-4-trifluoromethylphenyl) -5
To a mixture of 1.30 g (2.60 mmol) of-(N-ethoxycarbonylamino) -1,2,4-triazole and 13 ml of tetrahydrofuran was added 0.140 g (3.40 mmol) of sodium hydride (oily, containing about 60%). ) Was added under ice cooling, and the mixture was stirred for 15 minutes. Next, 0.320 g (3.40 mmol) of chloromethyl ethyl ether
And several drops of 15-crown-5, and the mixture was stirred at room temperature for 15 hours. After evaporating the solvent under reduced pressure, water was poured into the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography to give 3-dichlorofluoromethylsulfenyl-1-
(2,6-dichloro-4-trifluoromethylphenyl) -5- [N-ethoxycarbonyl-N- (ethoxymethyl) amino] -1,2,4-triazole [hereinafter,
[Compound 1 of the present invention] was obtained. 1 H-NMR (250 MHz, CDCl 3 / TMS): δ
(Ppm) = 7.75 (s, 2H), 5.09 (s, 2
H), 4.13 (q, J = 7.1 Hz, 2H), 3.60
(Q, J = 7.0 Hz, 2H), 1.16 (t, J = 7.
1 Hz, 3H), 1.08 (t, J = 7.0 Hz, 3H)
【0023】製造例2 水素化ナトリウム(油性、約60%含有)0.208g
(5.20ミリモル)をテトラヒドロフラン20mlに
懸濁した中に氷冷下、3−ジクロロフルオロメチルスル
フェニル−1−(2,6−ジクロロ−4−トリフルオロ
メチルフェニル)−5−(N−メトキシカルボニルアミ
ノ)−1,2,4−トリアゾール1.95g(4.00
ミリモル)を少しずつ加え、0℃から5℃にて30分間
攪拌した。次に15−クラウン−5を1滴、クロロメチ
ル メチル エーテル0.419g(5.20ミリモ
ル)を氷冷下加え、さらに室温にて5時間攪拌した。反
応液を水に注加し、酢酸エチルで抽出し、該有機層を無
水硫酸マグネシウムで乾燥した。減圧下に濃縮し、残渣
をシリカゲルカラムクロマトグラフィーに付し、3−ジ
クロロフルオロメチルスルフェニル−1−(2,6−ジ
クロロ−4−トリフルオロメチルフェニル)−5−〔N
−メトキシカルボニル−N−(メトキシメチル)アミ
ノ〕−1,2,4−トリアゾール〔以下、本発明化合物
2と記す〕1.50gを得た。1 H−NMR(250MHz,CDCl3/TMS):δ
(ppm)=7.76(s,2H),5.08(s,2
H),3.65(s ,3H),3.41(s ,3H )Production Example 2 0.208 g of sodium hydride (oil-based, containing about 60%)
(5.20 mmol) was suspended in 20 ml of tetrahydrofuran and cooled under ice-cooling to give 3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -5- (N-methoxy 1.95 g (4.00 of carbonylamino) -1,2,4-triazole
(Mmol) was added little by little, and the mixture was stirred at 0 to 5 ° C for 30 minutes. Next, one drop of 15-crown-5 and 0.419 g (5.20 mmol) of chloromethyl methyl ether were added under ice-cooling, and the mixture was further stirred at room temperature for 5 hours. The reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography to give 3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -5- [N
-Methoxycarbonyl-N- (methoxymethyl) amino] -1,2,4-triazole [hereinafter referred to as the present compound 2] 1.50 g was obtained. 1 H-NMR (250 MHz, CDCl 3 / TMS): δ
(Ppm) = 7.76 (s, 2H), 5.08 (s, 2
H), 3.65 (s, 3H), 3.41 (s, 3H)
【0024】製造例3 水素化ナトリウム(油性、約60%含有)0.208g
(5.20ミリモル)をテトラヒドロフラン20mlに
懸濁した中に氷冷下、3−ジクロロフルオロメチルスル
フェニル−1−(2,6−ジクロロ−4−トリフルオロ
メチルフェニル)−5−(N−メトキシカルボニルアミ
ノ)−1,2,4−トリアゾール1.95g(4.00
ミリモル)を少しずつ加え、0℃から5℃にて30分間
攪拌した。次に15−クラウン−5を1滴、クロロメチ
ル エチル エーテル0.492g(5.20ミリモ
ル)を氷冷下加え、さらに室温にて5時間攪拌した。反
応液を水に注加し、酢酸エチルで抽出し、該有機層を無
水硫酸マグネシウムで乾燥した。減圧下に濃縮して得ら
れた残渣をシリカゲルカラムクロマトグラフィーに付
し、3−ジクロロフルオロメチルスルフェニル−1−
(2,6−ジクロロ−4−トリフルオロメチルフェニ
ル)−5−〔N−メトキシカルボニル−N−(エトキシ
メチル)アミノ〕−1,2,4−トリアゾール〔以下、
本発明化合物3と記す〕1.50gを得た。1 H−NMR(250MHz,CDCl3/TMS):δ
(ppm)=7.76(s,2H),5.12(s,2
H),3.66(s ,3H), 3.65(q,J=7.0
Hz,2H ), 1.12(t,J=7.0Hz,3H)Production Example 3 0.208 g of sodium hydride (oil-based, containing about 60%)
(5.20 mmol) was suspended in 20 ml of tetrahydrofuran and cooled under ice-cooling to give 3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -5- (N-methoxy 1.95 g (4.00 of carbonylamino) -1,2,4-triazole
(Mmol) was added little by little, and the mixture was stirred at 0 ° C to 5 ° C for 30 minutes. Next, one drop of 15-crown-5 and 0.492 g (5.20 mmol) of chloromethyl ethyl ether were added under ice-cooling, and the mixture was further stirred at room temperature for 5 hours. The reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure was subjected to silica gel column chromatography to give 3-dichlorofluoromethylsulfenyl-1-
(2,6-dichloro-4-trifluoromethylphenyl) -5- [N-methoxycarbonyl-N- (ethoxymethyl) amino] -1,2,4-triazole [hereinafter,
1.50 g of the present compound 3) was obtained. 1 H-NMR (250 MHz, CDCl 3 / TMS): δ
(Ppm) = 7.76 (s, 2H), 5.12 (s, 2
H), 3.66 (s, 3H), 3.65 (q, J = 7.0)
Hz, 2H), 1.12 (t, J = 7.0 Hz, 3H)
【0025】参考製造例1 水素化ナトリウム(油性、約60%含有)2.2g(5
5ミリモル)およびテトラヒドロフラン250mlに懸
濁した中に氷冷化、5−アミノ−3−ジクロロフルオロ
メチルスルフェニル−1−(2,6−ジクロロ−4−ト
リフルオロメチルフェニル)−1,2,4−トリアゾール
10.8g(25ミリモル)を加え、15分間攪拌した。
次にクロロぎ酸エチル2.7g(25ミリモル)を加
え、室温で1時間攪拌した。減圧下に溶媒を留去した
後、残渣に水を注加し、酢酸エチルで抽出した。該有機
層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥
した。減圧下に濃縮し、残渣をシリカゲルカラムクロマ
トグラフィーに付し、3−ジクロロフルオロメチルスル
フェニル−1−(2,6−ジクロロ−4−トリフルオロ
メチルフェニル)−5−(N−エトキシカルボニルアミ
ノ)−1,2,4−トリアゾール10.0gを得た。1 H−NMR(250MHz,CDCl3/TMS):δ
(ppm)=8.32(br.s,1H),7.76(s,
2H),4.10(q,J=7.1Hz,2H),1.21
(t,J=7.1Hz,3H)Reference Production Example 1 2.2 g of sodium hydride (oil-based, containing about 60%)
5 mmol) and ice-cooled in suspension in 250 ml of tetrahydrofuran, 5-amino-3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -1,2,4. 10.8 g (25 mmol) of triazole were added and stirred for 15 minutes.
Next, 2.7 g (25 mmol) of ethyl chloroformate was added, and the mixture was stirred at room temperature for 1 hour. After evaporating the solvent under reduced pressure, water was poured into the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography to give 3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -5- (N-ethoxycarbonylamino) 10.0 g of -1,2,4-triazole was obtained. 1 H-NMR (250 MHz, CDCl 3 / TMS): δ
(Ppm) = 8.32 (br.s, 1H), 7.76 (s,
2H), 4.10 (q, J = 7.1 Hz, 2H), 1.21
(T, J = 7.1 Hz, 3H)
【0026】参考製造例2 3,3′−ジ〔5−アミノ−1−(2,6−ジクロロ−4
−トリフルオロメチルフェニル)−1,2,4−トリアゾ
リル〕ジスルフィド44.6g(68ミリモル)、N,N
−ジメチルホルムアミド408mlおよび水20mlの
混合物にヒドロキシメタンスルフィン酸ナトリウム二水
和物31.4g(204ミリモル)、トリクロロフルオ
ロメタン28.2g(204ミリモル)を10℃以下に
て加えた。添加後、室温で12時間攪拌した。反応混合
物を水に注加し、これを酢酸エチルで抽出した。該有機
層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥
した。減圧下に濃縮し、残渣をシリカゲルカラムクロマ
トグラフィーに付し、5−アミノ−3−ジクロロフルオ
ロメチルスルフェニル−1−(2,6−ジクロロ−4−
トリフルオロメチルフェニル)−1,2,4−トリアゾー
ル36.0gを得た。 m.p.205.7℃1 H−NMR(300MHz,CDCl3/TMS):δ
(ppm)=7.80(s,2H),4.78(br.s,2
H)Reference Production Example 2 3,3'-di [5-amino-1- (2,6-dichloro-4
-Trifluoromethylphenyl) -1,2,4-triazolyl] disulfide 44.6 g (68 mmol), N, N
-To a mixture of 408 ml of dimethylformamide and 20 ml of water were added 31.4 g (204 mmol) of sodium hydroxymethanesulfinate dihydrate and 28.2 g (204 mmol) of trichlorofluoromethane at 10 ° C or lower. After the addition, the mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into water, which was extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography to give 5-amino-3-dichlorofluoromethylsulfenyl-1- (2,6-dichloro-4-
36.0 g of (trifluoromethylphenyl) -1,2,4-triazole were obtained. 205.7 ° C. 1 H-NMR (300 MHz, CDCl 3 / TMS): δ
(Ppm) = 7.80 (s, 2H), 4.78 (br.s, 2
H)
【0027】次に製剤例を示す。尚、部は重量部を表
し、本発明化合物は前記の化合物番号で示す。 製剤例1 乳剤 本発明化合物1〜3の各々10部を、キシレン35部お
よびジメチルホルムアミド35部に溶解し、これにポリ
オキシエチレンスチリルフェニルエ−テル14部および
ドデシルベンゼンスルホン酸カルシウム6部を加え、よ
く攪拌混合して各々の10%乳剤を得る。 製剤例2 水和剤 本発明化合物1〜3の各々20部を、ラウリル硫酸ナト
リウム4部、リグニンスルホン酸カルシウム2部、合成
含水酸化珪素微粉末20部および珪素土54部を混合し
た中に加え、ジュ−スミキサ−で攪拌混合して各々の2
0%水和剤を得る。Next, preparation examples are shown. Parts represent parts by weight, and the compound of the present invention is represented by the aforementioned compound number. Formulation Example 1 Emulsion Ten parts of each of the present compounds 1 to 3 are dissolved in 35 parts of xylene and 35 parts of dimethylformamide, and 14 parts of polyoxyethylenestyrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added thereto. Mix well with stirring to obtain each 10% emulsion. Formulation Example 2 Wettable powder 20 parts of each of the present compounds 1 to 3 are added to a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium ligninsulfonate, 20 parts of synthetic hydrous silicon oxide fine powder and 54 parts of silicon earth. , And stirred with a Juice mixer to mix 2 parts of each.
0% wettable powder is obtained.
【0028】製剤例3 粒剤 本発明化合物1〜3の各々5部に、合成含水酸化珪素微
粉末5部、ドデシルベンゼンスルホン酸ナトリウム5
部、ベントナイト30部およびクレ−55部を加え充分
攪拌混合する。ついで、これらの混合物に適当量の水を
加え、さらに攪拌し、造粒機で製粒し、通風乾燥して各
々の5%粒剤を得る。 製剤例4 粉剤 本発明化合物1〜3の各々1部を適当量のアセトンに溶
解し、これに合成含水酸化珪素微粉末5部、PAP
0.3部およびクレ−93.7部を加え、ジュ−スミキ
サ−で攪拌混合し、アセトンを蒸発除去して各々の1%
粉剤を得る。Formulation Example 3 Granules 5 parts of each of Compounds 1 to 3 of the present invention, 5 parts of synthetic hydrous silicon oxide fine powder, 5 parts of sodium dodecylbenzenesulfonate
Parts, 30 parts of bentonite and 55 parts of clay are added and thoroughly mixed. Then, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain 5% granules of each. Formulation Example 4 Dust One part of each of Compounds 1 to 3 of the present invention is dissolved in an appropriate amount of acetone.
0.3 parts and Cle-93.7 parts were added, and the mixture was stirred and mixed with a Juice mixer, and acetone was evaporated to remove 1% of each.
Obtain a powder.
【0029】製剤例5 フロアブル剤 本発明化合物1〜3の各々20部とソルビタントリオレ
エ−ト1.5部とを、ポリビニルアルコ−ル2部を含む
水溶液28.5部と混合し、サンドグラインダ−で微粉
砕(粒径3μ以下)した後、この中に、キサンタンガム
0.05部およびアルミニウムマグネシウムシリケ−ト
0.1部を含む水溶液40部を加え、さらにプロピレン
グリコ−ル10部を加えて攪拌混合して各々の20%フ
ロアブル剤を得る。 製剤例6 油剤 本発明化合物1〜3の各々0.1部をキシレン5部およ
びトリクロロエタン5部に溶解し、これを脱臭灯油8
9.9部に混合して各々の0.1%油剤を得るFormulation Example 5 Flowable agent 20 parts of each of compounds 1 to 3 of the present invention and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, and the mixture is mixed with a sand grinder. After pulverizing (particle size: 3 μm or less), 40 parts of an aqueous solution containing 0.05 parts of xanthan gum and 0.1 parts of aluminum magnesium silicate are added thereto, and 10 parts of propylene glycol are further added. To obtain each 20% flowable. Formulation Example 6 Oil agent 0.1 part of each of the present compounds 1 to 3 is dissolved in 5 parts of xylene and 5 parts of trichloroethane, and this is deodorized kerosene 8
Mix 9.9 parts to obtain 0.1% oil for each
【0030】製剤例7 油性エアゾ−ル 本発明化合物1〜3の各々0.l部、テトラメトリン
0.2部、d−フェノトリン0.1部、トリクロロエタ
ン10部および脱臭灯油59.6部を混合溶解し、エア
ゾ−ル容器に充填し、バルブ部分を取り付けた後、該バ
ルブ部分を通じて噴射剤(液化石油ガス)30部を加圧
充填して各々の油性エアゾ−ルを得る。 製剤例8 水性エアゾ−ル 本発明化合物1〜3の各々0.2部、d−アレトリン
0.2部、d−フェノトリン0.2部、キシレン5部、
脱臭灯油3.4部および乳化剤(アトモス300(アト
ラスケミカル社登録商標名))1部を混合溶解したもの
と、純水50部とをエアゾ−ル容器に充填し、バルブ部
分を取り付け、該バルブ部分を通じて噴射剤(液化石油
ガス)40部を加圧充填して各々の水性エアゾ−ルを得
る。Formulation Example 7 Oily Azole 1 part, 0.2 part of tetramethrin, 0.1 part of d-phenothrin, 10 parts of trichloroethane and 59.6 parts of deodorized kerosene are mixed and dissolved, and the mixture is filled in an aerosol container, and the valve is attached. Then, 30 parts of a propellant (liquefied petroleum gas) is filled under pressure to obtain each oily aerosol. Formulation Example 8 aqueous azole 0.2 parts of each of the present compounds 1 to 3, 0.2 parts of d-alethrin, 0.2 parts of d-phenothrin, 5 parts of xylene,
A mixture of 3.4 parts of deodorized kerosene and 1 part of an emulsifier (Atmos 300 (registered trademark of Atlas Chemical)) and 50 parts of pure water were charged into an aerosol container, and a valve was attached. 40 parts of propellant (liquefied petroleum gas) are pressure-filled through the parts to obtain each aqueous aerosol.
【0031】製剤例9 蚊取り線香 本発明化合物1〜3の各々0.3gにd−アレトリン
0.3gを加え、アセトン20m1に溶解し、蚊取り線
香用担体(タブ粉:粕粉:木粉を4:3:3の割合で混
合)99.4gと均一に攪拌混合した後、水120ml
を加え、充分練り合わせたものを成型乾燥して各々の蚊
取り線香を得る。 製剤例10 電気蚊取マット 本発明化合物1〜3の各々0.4g、d−アレトリン
0.4gおよびピペニルブトキサイド0.4gにアセト
ンを加えて溶解し、全体で10mlとする。この溶液
0.5m1を、2.5cm×1.5cm、厚さ0.3c
mの電気マット用基材(コットンリンタ−とパルプの混
合物のフィブリルを板状に固めたもの)に均一に含浸さ
せて各々の電気蚊取マット剤を得る。Formulation Example 9 Mosquito Incense Incense 0.3 g of each of the present compounds 1 to 3 is added with 0.3 g of d-allethrin, dissolved in 20 ml of acetone, and a carrier for a mosquito incense stick (tab powder: meal powder: wood powder 4: 3). : 3)) 99.4g and uniformly stirred and mixed, then 120ml of water
, And the resulting mixture is molded and dried to obtain each mosquito coil. Formulation example 10 Electric mosquito collecting mat Acetone is added to each of 0.4 g of each of the present compounds 1 to 3, 0.4 g of d-allethrin, and 0.4 g of pipenyl butoxide to make 10 ml in total. 0.5 ml of this solution is 2.5 cm × 1.5 cm, thickness 0.3 c
m of an electric mat (a fibril of a mixture of cotton linter and pulp solidified into a plate) is uniformly impregnated to obtain each electric mosquito repellent.
【0032】製剤例11 加熱燻煙剤 本発明化合物1〜3の各々100mgを適量のアセトン
に溶解し、4.0cm×4.0cm、厚さ1.2cmの
多孔セラミック板に含浸させて各々の加熱燻煙剤を得
る。 製剤例12 毒餌 本発明化合物1〜3の各々10mgをアセトン0.5m
lに溶解し、この溶液を、動物用固型飼料粉末(飼育繁
殖用固型飼料粉夫CE−2、日本クレア株式会社商品
名)5gに処理し、均一に混合する。ついでアセトンを
風乾し、各々の0.2%毒餌を得る。Formulation Example 11 Heat Smoke Agent 100 mg of each of the present compounds 1 to 3 is dissolved in an appropriate amount of acetone, and impregnated into a porous ceramic plate having a size of 4.0 cm × 4.0 cm and a thickness of 1.2 cm. Obtain a heat smoker. Formulation Example 12 Poison bait 10 mg of each of Compounds 1 to 3 of the present invention was added to acetone 0.5 m
The resulting solution is treated with 5 g of solid feed powder for animals (solid feed powder for breeding and breeding, CE-2, trade name of Nippon Clea Co., Ltd.) and uniformly mixed. The acetone is then air dried to obtain each 0.2% poison bait.
【0033】製剤例13 防ダニシ−ト 本発明化合物1〜3の各々をアセトンで希釈し、不織布
に1m2当たり1gとなるように滴下含浸し、アセトン
を風乾して各々の防ダニシ−トを得る。 製剤例14 防ダニシ−ト 本発明化合物1〜3の各々をアセトンで希釈し、ろ紙に
1m2当たり1gとなるように滴下含浸し、アセトンを
風乾し、各々の防ダニシ−トを得る。 製剤例15 スポットオン剤 本発明化合物1〜3の各々5部と、ジエチレングリコー
ルモノエチルエーテル95部とを加え混合し、各々の5
%スポットオン剤を得る。Formulation Example 13 Anti-mite sheet Each of Compounds 1 to 3 of the present invention is diluted with acetone, impregnated into a non-woven fabric in an amount of 1 g per 1 m 2 , and the acetone is air-dried to give each anti-mite sheet. obtain. Formulation Example 14 Anti Danishi - each of the bets present compounds 1-3 was diluted with acetone, filter paper was added dropwise impregnated so that 1 m 2 per 1g, acetone air dried, each proof Danishi - get the door. Formulation Example 15 Spot-on agent 5 parts of each of the present compounds 1 to 3 and 95 parts of diethylene glycol monoethyl ether were added and mixed, and 5 parts of each compound was added.
% Spot-on agent is obtained.
【0034】次に本発明化合物が、殺虫剤の有効成分と
して有用であり、かつ哺乳動物に対する安全性に優れる
ことを試験例により示す。尚、本発明化合物は前記の化
合物番号で示す。また、比較対照化合物として、特開平
10−158250号公報に記載の1−(2,6−ジク
ロロ−4−トリフルオロメチルフェニル)−5−〔N,
N−ジ(エトキシカルボニル)アミノ〕−3−トリフル
オロメチルスルフェニル−1,2,4−トリアゾール〔以
下、比較化合物Aと記す。〕を用いた。Next, Test Examples show that the compound of the present invention is useful as an active ingredient of an insecticide and has excellent safety for mammals. The compounds of the present invention are indicated by the above compound numbers. As a comparative control compound, 1- (2,6-dichloro-4-trifluoromethylphenyl) -5- [N, described in JP-A-10-158250.
N-di (ethoxycarbonyl) amino] -3-trifluoromethylsulfenyl-1,2,4-triazole [hereinafter referred to as comparative compound A. ] Was used.
【0035】試験例1(ラット急性経口毒性試験) 7週令のCRj:CD(SD)IGS系ラットを用いて
急性経口毒性を検討した。供試化合物の各々をコーンオ
イルで10mg/mlになるように調製した後、約20
時間絶食したラット(体重210〜229g)に10m
l/kg体重の割合で強制的に胃内に投与した後、投与
後4時間目の観察終了後より餌および水を与えて7日間
飼育した。飼育期間中における死亡状況を観察した結果
を表1に示す。Test Example 1 (Acute oral toxicity test in rats) Acute oral toxicity was examined using 7 weeks old CRj: CD (SD) IGS rats. After adjusting each of the test compounds to 10 mg / ml with corn oil, about 20 mg
10m to rats (weight 210-229g) fasted for an hour
After being forcibly administered to the stomach at a rate of 1 / kg body weight, food and water were given from the end of observation 4 hours after administration, and the animals were bred for 7 days. Table 1 shows the results of observing the state of death during the breeding period.
【表1】 [Table 1]
【0036】試験例2(チャバネゴキブリ局所施用試
験) 本発明化合物1〜3および比較化合物Aの各々0.2μ
g/μlのアセトン溶液1μlをチャバネゴキブリ(B
lattella germanica)雌成虫の胸部
腹面に処理し、餌(ラット飼育用固形飼料;オリエンタ
ル酵母工業株式会社製)および水を与えた。処理7日後
に死虫率を求めた(1群 10頭、3反復)。本発明化
合物1〜3および比較化合物Aは全て死虫率100%を
示した。 試験例3(イエバエ濾紙接触試験) 直径5.5cmのポリエチレンカップの底に同大のろ紙
を敷き、製剤例1に準じて得られた本発明化合物1〜3
および比較化合物Aの各々の乳剤を、有効成分濃度が5
00ppmになるように水で希釈し、該希釈液0.7m
lを濾紙上に滴下し、餌としてショ糖30mgを均一に
入れた。その中に、イエバエ(Musca domes
tica)雌成虫10頭を放ち、蓋をして24時間後に
その生死を調査し、死虫率を求めた。本発明化合物1〜
3は全て死虫率100%を示し、比較化合物Aは死虫率
90%を示した。 試験例4(噴霧処理したマウスを用いたネコノミ寄生試
験) 本発明化合物1〜3の各々0.005重量%のエタノー
ル溶液2mlを、マウス(Std:ddY系統、雌、1
0週令、生体重約30g)の体表に均一にアトマイザー
にて噴霧処理した。数分間、風乾させた後、このマウス
を袋状の金網内に入れ固定し、これをガラス瓶内に入れ
た。続いて、ガラス瓶内にネコノミ(Ctenocep
halides felis)成虫20頭を入れ、該マ
ウスに寄生させ、2日後に死虫率を求めた(2反復)。
本発明化合物1〜3は全て死虫率90%以上を示した。 試験例5(経口投与したマウスを用いたネコノミ寄生試
験) 本発明化合物1〜3の各々をコーンオイルで2mg/m
lになるように調整した後、マウス(Std:ddY系
統、雌、10週令、生体重約30g)に10ml/kg
体重の割合(20mg/kg)で強制的に胃内に投与し
た。投与後のマウスを袋状の金網内に入れ固定し、これ
をガラス瓶内に入れた。続いて、ガラス瓶内にネコノミ
(Ctenocephalides felis)成虫
20頭を入れ、該マウスに寄生させ、1日後にネコノミ
の死虫率を求めた(3反復)。本発明化合物1〜3は全
て死虫率90%以上を示した。 試験例6(シロアリ局所施用試験) 供試化合物0.1重量%のアセトン溶液0.2μlをイ
エシロアリ(Coptotermes formosa
nus)職蟻胸部背板に処理し、これを底部に水に湿ら
せた濾紙を敷いた直径9cmの樹脂シャーレ内に移し
た。処理7日後に死虫率を求めた(1群10頭、3反
復)。本発明化合物1〜3は全て死虫率100%を示し
た。Test Example 2 (Test for topical application of German cockroaches) Compounds 1 to 3 of the present invention and 0.2 μm each of comparative compound A
g / μl of an acetone solution (1 μl) was mixed with German cockroaches (B
The adult female (Lattella germanica) was treated on the thoracic ventral surface and fed with food (solid feed for raising rats; Oriental Yeast Co., Ltd.) and water. Seven days after the treatment, the mortality was determined (10 animals per group, 3 repetitions). Inventive Compounds 1 to 3 and Comparative Compound A all showed a mortality of 100%. Test Example 3 (Housefly filter paper contact test) A filter paper of the same size was spread on the bottom of a polyethylene cup having a diameter of 5.5 cm, and the compounds of the present invention 1 to 3 obtained according to Formulation Example 1.
Each of the emulsions of Comparative Compound A and Comparative Compound A was used when the active ingredient concentration was 5
Diluted with water to give a concentration of 0.7 ppm
was dropped on a filter paper, and 30 mg of sucrose was uniformly added as a bait. Among them, housefly (Musca domes)
tica) Ten adult females were released, and after 24 hours with the lid covered, their survival was examined to determine the mortality. Compound 1 of the present invention
3 all showed 100% mortality, and Comparative Compound A showed 90% mortality. Test Example 4 (Cat flea parasite test using spray-treated mice) 2 ml of a 0.005 wt% ethanol solution of each of Compounds 1 to 3 of the present invention was administered to mice (Std: ddY strain, female, 1
A 0 week-old body weight of about 30 g of living weight) was uniformly sprayed with an atomizer. After air-drying for several minutes, the mouse was placed and fixed in a bag-shaped wire mesh and placed in a glass bottle. Next, the cat flea (Ctenocep) was placed in the glass bottle.
20 adults were infested with the mice and two days later, the mortality was determined (two replicates).
All of the present compounds 1 to 3 showed a mortality of 90% or more. Test Example 5 (Cat flea parasitic test using orally administered mouse) Each of the present compounds 1 to 3 was 2 mg / m2 in corn oil.
After adjusting to be 1 l, a mouse (Std: ddY strain, female, 10 weeks old, live weight of about 30 g) was added to a mouse at 10 ml / kg.
It was forcibly administered intragastrically at the rate of body weight (20 mg / kg). After administration, the mouse was placed in a bag-shaped wire net and fixed, and this was placed in a glass bottle. Subsequently, 20 cat flea (Ctenocephalides felis) adults were placed in a glass bottle, and the mice were parasitized. One day later, the mortality of the cat flea was determined (3 replicates). All of the present compounds 1 to 3 showed a mortality of 90% or more. Test Example 6 (Termite application topical test) 0.2 μl of an acetone solution containing 0.1% by weight of a test compound was added to a house termite (Copttermes formosa).
nus) The ant's chest back plate was treated and transferred to a 9 cm diameter resin petri dish with a filter paper moistened with water at the bottom. Seven days after the treatment, the mortality was determined (10 animals per group, 3 repetitions). All of the present compounds 1 to 3 exhibited a mortality of 100%.
【発明の効果】本発明化合物は、有効な殺虫、殺ダニ、
殺線虫活性を有するとともに、哺乳動物に対して優れた
安全性を有する。Industrial Applicability The compound of the present invention is effective for killing insects, killing mites,
It has nematicidal activity and excellent safety for mammals.
Claims (2)
ルボニル基を表し、R1がエトキシカルボニル基の場
合、R2はエトキシメチル基を表し、R1がメトキシカル
ボニル基の場合、R2はエトキシメチル基またはメトキ
シメチル基を表す。]で示されるトリアゾール化合物。1. A compound represented by the general formula: [Wherein, R 1 represents an ethoxycarbonyl group or a methoxycarbonyl group, R 1 represents an ethoxycarbonyl group, R 2 represents an ethoxymethyl group, and R 1 represents a methoxycarbonyl group, and R 2 represents an ethoxymethyl group. Or a methoxymethyl group. ] The triazole compound shown by these.
含有することを特徴とする殺虫、殺ダニ、殺線虫剤。2. An insecticide, acaricide, and nematicide comprising the compound according to claim 1 as an active ingredient.
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006043635A1 (en) * | 2004-10-20 | 2006-04-27 | Kumiai Chemical Industry Co., Ltd. | 3-triazolylphenyl sulfide derivative and insecticide/acaricide/nematicide containing the same as active ingredient |
CN103664811A (en) * | 2007-11-30 | 2014-03-26 | 庵原化学工业株式会社 | Aryl (1h-1,2,4-triazol-1-yl) compound, and process for production thereof |
-
1999
- 1999-02-17 JP JP11038493A patent/JP2000239262A/en active Pending
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006043635A1 (en) * | 2004-10-20 | 2006-04-27 | Kumiai Chemical Industry Co., Ltd. | 3-triazolylphenyl sulfide derivative and insecticide/acaricide/nematicide containing the same as active ingredient |
JPWO2006043635A1 (en) * | 2004-10-20 | 2008-05-22 | クミアイ化学工業株式会社 | 3-Triazolylphenyl sulfide derivatives and insecticides, acaricides, nematicides containing them as active ingredients |
US7872036B2 (en) | 2004-10-20 | 2011-01-18 | Kumiai Chemical Industry Co., Ltd. | 3-triazolylphenyl sulfide derivative and insecticide, miticide and nematicide containing it as an active ingredient |
CN101039922B (en) * | 2004-10-20 | 2011-04-13 | 组合化学工业株式会社 | 3-triazolylphenyl sulfide derivative and insecticide/acaricide/nematicide containing the same as active ingredient |
CN103664811A (en) * | 2007-11-30 | 2014-03-26 | 庵原化学工业株式会社 | Aryl (1h-1,2,4-triazol-1-yl) compound, and process for production thereof |
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