JPH03232805A - Use of trihaloimidazole derivative as insecticide and acaricide - Google Patents
Use of trihaloimidazole derivative as insecticide and acaricideInfo
- Publication number
- JPH03232805A JPH03232805A JP2771090A JP2771090A JPH03232805A JP H03232805 A JPH03232805 A JP H03232805A JP 2771090 A JP2771090 A JP 2771090A JP 2771090 A JP2771090 A JP 2771090A JP H03232805 A JPH03232805 A JP H03232805A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- compound
- expressed
- parts
- 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
- 230000000895 acaricidal effect Effects 0.000 title claims abstract description 20
- 239000002917 insecticide Substances 0.000 title claims abstract description 14
- 239000000642 acaricide Substances 0.000 title claims abstract description 10
- 239000004480 active ingredient Substances 0.000 claims abstract description 13
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 4
- 125000002541 furyl group Chemical group 0.000 claims abstract description 3
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 39
- 239000000203 mixture Substances 0.000 abstract description 36
- -1 (substituted) phenyl Chemical group 0.000 abstract description 18
- 241000607479 Yersinia pestis Species 0.000 abstract description 14
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- JCGGPCDDFXIVQB-UHFFFAOYSA-N 2,4,5-tribromo-1h-imidazole Chemical compound BrC1=NC(Br)=C(Br)N1 JCGGPCDDFXIVQB-UHFFFAOYSA-N 0.000 abstract description 2
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- 235000019483 Peanut oil Nutrition 0.000 description 1
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
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- 241001247145 Sebastes goodei Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
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- 239000005667 attractant Substances 0.000 description 1
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- VJRITMATACIYAF-UHFFFAOYSA-N benzenesulfonohydrazide Chemical compound NNS(=O)(=O)C1=CC=CC=C1 VJRITMATACIYAF-UHFFFAOYSA-N 0.000 description 1
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- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
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- 239000003575 carbonaceous material Substances 0.000 description 1
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- 210000000038 chest Anatomy 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
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- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
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- 239000000417 fungicide Substances 0.000 description 1
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- 150000002357 guanidines Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
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- 239000004615 ingredient Substances 0.000 description 1
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- 150000002823 nitrates Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
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- 239000005017 polysaccharide Substances 0.000 description 1
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
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- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
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- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
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- 239000011593 sulfur Substances 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明はトリハロイミダゾール誘導体の殺虫、殺ダニ剤
としての用途に関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to the use of trihaloimidazole derivatives as insecticides and acaricides.
〈従来の技術〉
ある種のトリハロイミダゾール誘導体、たとえば１−ア
セトキシメチル−２，４，５−トリブロモイミダゾール
が除草剤の有効が・分として用いられ得ることは特公昭
４２−１６９１９２号公報に記載されている。<Prior Art> It is described in Japanese Patent Publication No. 169192/1983 that certain trihaloimidazole derivatives, such as 1-acetoxymethyl-2,4,5-tribromoimidazole, can be used as effective herbicides. has been done.
他方、１−ｎ−ペンチルオキシメチル−２，４，５−ト
リクロロイミダゾールが殺虫剤、とりわけゴキブリ用殺
虫剤の有効成分として用いられ得ることは、イギリス特
許第１，８１６，６６５号明細舎および米国特許第８，
６７４，８７４号明細誓等に記載されている。On the other hand, it has been shown in British Patent No. 1,816,665 and in the United States that 1-n-pentyloxymethyl-2,4,5-trichloroimidazole can be used as an active ingredient in insecticides, especially insecticides for cockroaches. Patent No. 8,
It is stated in No. 674,874.
〈発明が解決しようとする課題〉
しかしながら、イギリス特許第１，８１６，６６５号明
和」参およびオ国忙許第８，６７４，８７４月明細仏に
１和されている化合物は、も）虫、殺タ゛二剤の有ダ、
成分として必ずしも常に充分なものであるとはいえない
。<Problems to be Solved by the Invention> However, the compounds disclosed in British Patent No. 1,816,665 Meiwa and Japanese Patent No. 8,674,874 are also harmful to insects, Presence of antibacterial agent,
It cannot be said that it is always sufficient as a component.
く課題を解決するための手段〉
本発明者らは、上記の状況に鍋み、よりすぐれた殺虫、
殺ダニ効力を有する化合物を見出すべく鋭意検討を重ね
た結果、−１式〔■〕
δ
〔式中、Ｋは水素原子、アルキル基、置換アルキル基、
アルケニル基、フリル基、フェニル基、置換フェニル基
、シクロアルキル系、ビシクロアルケニル基またはチエ
ニル基を表わし、Ｒはアルキル基、アルケニル基、ハロ
アルキル基またはシクロアルキル基を表わす。〕
で示されるトリハロイミダゾール誘導体（以下、化合物
ｒＩ）と記す。）が、
１、きわめて高い殺虫、殺ダニ効力を有する。Means for Solving the Problems〉 The present inventors have addressed the above situation and have devised a better insecticide.
As a result of intensive studies to find a compound with acaricidal effect, we found that -1 formula [■] δ [wherein K is a hydrogen atom, an alkyl group, a substituted alkyl group,
It represents an alkenyl group, a furyl group, a phenyl group, a substituted phenyl group, a cycloalkyl group, a bicycloalkenyl group or a thienyl group, and R represents an alkyl group, an alkenyl group, a haloalkyl group or a cycloalkyl group. ] The trihaloimidazole derivative represented by (hereinafter referred to as compound rI). ) has extremely high insecticidal and acaricidal efficacy.
２、ノックダウン効力、致死効力双方ともに優れる。2. Excellent knockdown efficacy and lethal efficacy.
８ピレスロイド低感受性害虫に対し、顕著な殺虫、殺ダ
ニ効力を発揮する。Demonstrates remarkable insecticidal and acaricidal efficacy against pests that are not sensitive to 8-pyrethroids.
４、燻煙剤としての効力が高い。4. Highly effective as a smoking agent.
等の全く新しい殺虫、殺ダニ特性を有することを見出し
、本発明に至った。It was discovered that it has completely new insecticidal and acaricidal properties, such as, and led to the present invention.
化合物〔ηの一部は、すでに特公昭４２−１６１９２号
公報によって知られてはいるが、該公報には、化合物α
〕が、かかる殺虫、殺ダニ特性を有することについては
、何ら記載されておらず、本発明者らが初めて見出した
ものである。Although a part of the compound [η is already known from Japanese Patent Publication No. 42-16192, the publication does not include the compound α
] has such insecticidal and acaricidal properties, which is the first discovery by the present inventors.
化合物α〕は、網翅目害虫、半翅目害虫、双翅目害虫等
の各種衛生害虫、農業害虫等多くの害虫および有害ダニ
類に対して殺虫、殺ダニ効力を自し、特にチャバネゴキ
ブリ、ワモンゴキブリ、クロゴキブリ、トビイロゴキブ
リ、コバネゴキブリ等のゴキブリ類に有効である。Compound α] has insecticidal and acaricidal effects against various sanitary pests such as Apiptera pests, Hemiptera pests, and Diptera pests, agricultural pests, and harmful mites, and is particularly effective against German cockroaches, It is effective against cockroaches such as the American cockroach, black cockroach, brown cockroach, and small cockroach.
したがって、化合物α〕は、多くの場面で問題となる害
虫および有害ダニ類に対して有効な殺虫、殺ダニ剤の有
効成分として用いることができる。Therefore, compound α] can be used as an active ingredient of insecticides and acaricides that are effective against pests and harmful mites that are problematic in many situations.
−最大α〕中、Ｒが置換アルキル基である場合の置換基
としては、たとえはアルコキシ基、アルキルチオ基、フ
ェニル基またはシアノ基等があげられ、置換フェニル基
である場合の置換基としては、たとえばアルキル基、ハ
ロゲン原子、アルコキシ基、フェニル基、ハロアルキル
基、フェノキシ基、アルキルチオ基、ニトロ基、シアノ
基またはシアφ
ルキルアミ基等があげられる。- maximum α], examples of the substituent when R is a substituted alkyl group include an alkoxy group, an alkylthio group, a phenyl group, or a cyano group, and when it is a substituted phenyl group, examples of the substituent include: Examples include an alkyl group, a halogen atom, an alkoxy group, a phenyl group, a haloalkyl group, a phenoxy group, an alkylthio group, a nitro group, a cyano group, and a siaφalkylami group.
化合物ＣＩ）は、たとえば特公昭４２−１６９１９２号
公報に記載されている方法等で製造することができる。Compound CI) can be produced, for example, by the method described in Japanese Patent Publication No. 42-169192.
すなわち、２，４．５−トリブロモイミダゾールと一般
式（３）
％式％［］
ｃ式中、Ｒ１は前記と同じ意味を表わす。〕で示される
アルデヒドないしはホルムアルデヒド（５〕
の場合には、供給体となるパラホルムアルデヒドまたは
ｓｙｍ−）リオキサンと一最大輿は非共存下に反応させ
ることによって製造できる。That is, 2,4.5-tribromoimidazole and the general formula (3) % formula % [ ] c In the formula, R1 represents the same meaning as above. ] In the case of aldehyde or formaldehyde (5), it can be produced by reacting it with paraformaldehyde or sym-)lioxane as a feeder in the absence of the coexistence.
反応に供する試剤の量は、２．４ 、５−）ジブロモイ
ミダゾール１当量に対してアルデヒド〔用１〜２当量、
酸蕪水物（ロ）は１〜１０当量であり、これらを俗媒中
または無溶媒で、酸触媒の存在下あるいは非共存下に０
〜１５０℃で１〜２４時間程度反応させる。The amount of the reagent used in the reaction is 1 to 2 equivalents of aldehyde per 1 equivalent of 2.4,5-)dibromoimidazole,
The acid turnip hydrate (b) is 1 to 10 equivalents, and is dissolved in a common medium or without a solvent in the presence or absence of an acid catalyst.
React at ~150°C for about 1 to 24 hours.
上記の本反応に用いられる溶媒としては、たとえはヘキ
サン、ヘプタン、リグロイン、石油エーテル等の脂肪族
炭化水素類、ベンゼン、トルエン、キシレン等の芳香族
炭化水素類、クロロホルム、四塩化炭素、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
炭化水素類、シ（６）
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類、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
ノン等のケトン類、蟻酸エチル、酢酸エチル、酢酸ブチ
ル、炭酸ジエチル等のエステル類、ニトロエタン、ニト
ロベンゼン等のニトロ化物、アセトニトリル、イソブチ
ロニトリル等のニトリル類、ピリジン、トリエチルアミ
ン、Ｎ、Ｎ−ジエチルアニリン、トリブチルアミン、Ｎ
−メチルモルホリン等の第三級アミン類、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等あるいはそれらの混合物があ
げられる。Examples of the solvent used in the above reaction include aliphatic hydrocarbons such as hexane, heptane, ligroin, and petroleum ether, aromatic hydrocarbons such as benzene, toluene, and xylene, chloroform, carbon tetrachloride, dichloroethane, Halogenated hydrocarbons such as chlorobenzene and dichlorobenzene, ethers such as (6) ethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, and cyclohexanone; Esters such as ethyl formate, ethyl acetate, butyl acetate, diethyl carbonate, nitrites such as nitroethane and nitrobenzene, nitriles such as acetonitrile and isobutyronitrile, pyridine, triethylamine, N,N-diethylaniline, tributylamine, N
Examples include tertiary amines such as methylmorpholine, acid amides such as formamide, N,N-dimethylformamide and N,N-dimethylacetamide, sulfur compounds such as dimethylsulfoxide and sulfolane, and mixtures thereof.
酸触媒としては、有機スルホン酸、たとえばメタンスル
ホン酸、ベンゼンスルホン酸またはトルエンスルホン酸
等があげられる。Examples of the acid catalyst include organic sulfonic acids such as methanesulfonic acid, benzenesulfonic acid, and toluenesulfonic acid.
反応終了後は、通常の後処理を行ない、必要ならばクロ
マトグラフィー、蒸留、再結晶等によっセ精製すること
ができる。After the reaction is completed, usual post-treatments are carried out, and if necessary, purification can be carried out by chromatography, distillation, recrystallization, etc.
化合物ＣＩ）を殺虫、殺ダニ剤の有効成分として用いる
場合は、通常、固体担体、液体担体、ガス状担体、餌と
混合するか、あるいは蚊取線香やマット、プレート等の
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、水中懸濁剤、
水中乳濁剤等のフロアブル剤、粒剤、粉剤、エアゾール
、蚊取線香・電気蚊取マット・ノーマット等の加熱燻蒸
剤、自己燃焼型燻煙剤・化学反応型燻煙剤・電熱型燻煙
剤等の加熱燻煙剤、樹脂蒸散剤、含浸紙蒸散剤等の非加
熱蒸散剤、フォッギング等の煙霧剤、ＵＬＹ剤、毒餌等
に製剤して使用する。When compound CI) is used as an active ingredient in insecticides or acaricides, it is usually mixed with a solid carrier, liquid carrier, gaseous carrier, or bait, or impregnated into a substrate such as a mosquito coil, mat, or plate. , if necessary, add surfactants and other formulation auxiliaries to prepare oils, emulsions, wettable powders, suspensions in water,
Flowable agents such as water emulsions, granules, powders, aerosols, heating fumigants such as mosquito coils, electric mosquito repellent mats, no-mats, self-combustion type smokers, chemical reaction type smokers, and electric heating type smokers. It is used in formulations such as heating fumigants, resin transpiration agents, non-heat transpiration agents such as impregnated paper transpiration agents, fogging agents such as fogging agents, ULY agents, poison baits, etc.
これらの製剤には、有効成分として化合物［Ｉ］を、通
割、重量比で０００１〜９５％含有する。These preparations contain Compound [I] as an active ingredient in an amount of 0001 to 95% by weight.
製剤化の際に用いられる固体担体としては、たとえば粘
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、線素、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、たとえ
ば水、アルコール類（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Ｗ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、幻油、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
ピルエーテル、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かあげられ、ガス状担体、す
なわち噴射剤としては、たとえばフロンガス、ブタンガ
ス、ＬＰＧ（液化石油ガス）、ジメチルエーテル、炭酸
ガス等があげられる。Solid carriers used in formulation include, for example, clays (kaolin clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, fubasami clay, acid clay, etc.), talcs, ceramics, and other inorganic minerals (sericite, quartz,
Sulfur, activated carbon, calcium carbonate, hydrated silica, etc.), chemical fertilizers (ammonium sulfate, ammonium phosphorus, ammonium nitrate, wire element, ammonium chloride, etc.), etc., fine powders or granules, and liquid carriers include, for example, water, Alcohols (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic W group hydrocarbons (benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, phantom oil, light oil, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, dioxane, etc.), acid amides (N, N dimethylformamide, N, N - dimethylacetamide, etc.], halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), dimethyl sulfoxide, vegetable oils such as soybean oil, cottonseed oil, etc. Gaseous carriers, that is, propellants, include, for example, chlorofluorocarbon gas, Examples include butane gas, LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide gas, etc.
（９〕
界面活性剤としては、たとえばアルキル硫酸工鹸
ステル類、アルキルスルホン塩基、アルキルアリールス
ルホン酸塩、アルキルアリールエー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ールエーテ
ル類、多価アルコールエステル類、糖アルコール誘導体
等かあげられる。(9) Surfactants include, for example, alkyl sulfate esters, alkyl sulfone bases, alkylaryl sulfonates, alkylaryl ethers and their polyoxyethylenic products, polyethylene glycol ethers, polyhydric alcohol esters, and sugars. Examples include alcohol derivatives.
固着剤や分散剤等の製剤用補助剤としては、たとえばカ
ゼイン、ゼラチン、多糖類（でんぷん粉、アラビアガム
、セルロース誘導体、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
アルコール、ポリビニルピロリドン、ポリアクリル酸類
等）があげられ、安定剤としては、たとえばＰＡＰ（酸
性リン酸イソプロピル）、Ｂ）ｉＴ（２，６−シーｔｅ
ｒｔ−ブチル−４−メチルフ、 ／ −ＪＬ／ ）、Ｂ
ＨＡ （２−ｔｅｒｔ−ブチル−４−メトキシフェノー
ルと３−ｔｅｒｔ−ブチル−４−メトキシフェノールと
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 formulation aids such as fixing agents and dispersants include casein, gelatin, polysaccharides (starch powder, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers (polyvinyl alcohol, etc.) , polyvinylpyrrolidone, polyacrylic acids, etc.), and examples of stabilizers include PAP (isopropyl acid phosphate), B) iT (2,6-sheet
rt-butyl-4-methylph, / -JL/ ), B
Examples include HA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil, surfactants, fatty acids or esters thereof, and the like.
蚊取線香の基材としては、たとえば木粉、粕粉（１０）
等の植物性粉末とタブ粉、スターチ、グルティン等の結
合剤との混合物等があげられる。Examples of the base material for mosquito coils include mixtures of vegetable powders such as wood flour and lees powder (10) and binders such as tab flour, starch, and gluten.
電気蚊取マットの基材としては、たとえばコツトンリン
ターまたはコツトンリンターとパルプとの混合物のフィ
ブリルを板状に固めたもの等があげられる。Examples of the base material for the electric mosquito repellent mat include fibrils of cotton linters or a mixture of cotton linters and pulp solidified into a plate shape.
自己燃焼型燻煙剤の基材としては、たとえば硝酸塩、亜
硝酸塩、グアニジン塩、塩素酸カリウム、ニトロセルロ
ーズ、エチルセルローズ、木粉等の燃焼発熱剤、アルカ
リ金属塩、アルカリ土類金属塩、重クロム酸塩、クロム
酸塩等の熱分解刺激剤、硝酸カリウム等の酸素供給剤、
メラミン、小麦デンプン等の支燃剤、硅礫土等の増量剤
、合成糊料等の結合剤等があげられる。Examples of base materials for self-combusting smoke agents include nitrates, nitrites, guanidine salts, potassium chlorate, nitrocellulose, ethylcellulose, combustion exothermic agents such as wood flour, alkali metal salts, alkaline earth metal salts, heavy Pyrolysis stimulators such as chromate, chromate, oxygen supply agents such as potassium nitrate,
Examples include combustion supporting agents such as melamine and wheat starch, fillers such as quartz clay, and binders such as synthetic glues.
化学反応型燻煙剤の基材としては、たとえばアルカリ金
属の硫化物、多硫化物、水硫化物、含水塩、酸化カルシ
ウム等の発熱剤、炭素質物質、炭化鉄、活性白土等の触
媒剤、アゾジカルボンアミド、ベンゼンスルホニルヒド
ラジド、ジニトロソペンタメチレンテトラミン、ポリス
チレン、ポリウレタン等の有機発泡剤、天然繊維片、合
成繊維片等の充填剤等があげられる。The base materials for chemically reactive smoke agents include, for example, exothermic agents such as alkali metal sulfides, polysulfides, hydrosulfides, hydrated salts, and calcium oxide, and catalyst agents such as carbonaceous substances, iron carbide, and activated clay. , organic blowing agents such as azodicarbonamide, benzenesulfonyl hydrazide, dinitrosopentamethylenetetramine, polystyrene, and polyurethane, and fillers such as natural fiber pieces and synthetic fiber pieces.
電熱型燻煙剤の基材としては、たとえば多孔セラミック
板、アスベスト板、パルプ板、多孔性ガラス材料等があ
げられる。Examples of the base material for the electrothermal smoke agent include porous ceramic plates, asbestos plates, pulp plates, porous glass materials, and the like.
非加熱蒸散剤の基材としては、たとえば熱可塑油、糖、
結晶セルローズ等の餌成分、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ン酸等の酸化防止剤、デ
ヒドロ酢酸等の保存料、トウガラシ末等の誤食防止剤・
、チーズ香料、タマネギ香料、ビーナツツオイル等の誘
引剤等があげられる。Examples of base materials for non-thermal transpiration agents include thermoplastic oil, sugar,
Feed ingredients such as crystalline cellulose, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, and agents to prevent accidental ingestion such as chili pepper powder.
, cheese flavoring, onion flavoring, peanut oil, and other attractants.
フロアブル剤（水中懸濁剤または水中乳濁剤）の製剤は
、一般に１〜７５％の有効成分化合物を、０．５〜１５
％の分散剤、０．１〜１０％の懸濁助剤（たとえば、保
護コロイドやチクソトロピー性を付与する化合物）、０
〜１０％の適当な補助剤（たとえば、消泡剤、防錆剤、
安定化剤、展着剤、浸透助剤、凍結防止剤、防菌剤、防
御剤等）を含む水中で微小に分散させることによって得
られる。Flowable formulations (suspensions or emulsions in water) generally contain 1 to 75% of the active ingredient compound and 0.5 to 15% of the active ingredient.
% dispersant, 0.1-10% suspension aid (e.g., protective colloid or compound imparting thixotropic properties), 0.
~10% of suitable adjuvants (e.g. defoamers, rust inhibitors,
It can be obtained by finely dispersing it in water containing a stabilizer, a spreading agent, a penetration aid, an antifreeze agent, an antibacterial agent, a protective agent, etc.).
水の代わりに有効成分化合物がほとんど溶解しない油を
用いて油中懸濁剤とすることも可能である。It is also possible to use an oil in which the active ingredient is hardly soluble instead of water to form a suspension in oil.
保護コロイドとしては、たとえばゼラチン、カゼイン、
ガム類、セルロースエーテル、ポリビニルアルコール等
が用いられる。チクソトロピー性を付与する化合物とし
ては、たとえばベントナイト、アルミニウムマグネシウ
ムシリケート、キサンタンガム、ポリアクリル酸等があ
げられる。Examples of protective colloids include gelatin, casein,
Gums, cellulose ether, polyvinyl alcohol, etc. are used. Examples of compounds that impart thixotropy include bentonite, aluminum magnesium silicate, xanthan gum, and polyacrylic acid.
このようにして得られる製剤は、そのままであるいは水
等で希釈して用いる。また、他の殺虫剤、除
殺ダニ剤、殺線虫剤、土壌害虫防止剤、害虫忌避剤、殺
菌剤、除草剤、植物生長調節剤、共力剤、肥料、土壌改
良剤と混合して、または混合せずに同時に用いることも
できる。The preparation thus obtained is used as it is or diluted with water or the like. It can also be mixed with other insecticides, acaricides, nematicides, soil pest prevention agents, pest repellents, fungicides, herbicides, plant growth regulators, synergists, fertilizers, and soil conditioners. , or can be used simultaneously without mixing.
化合物ＣＩ）を農業用殺虫、殺ダニ剤の有効成分として
用いる場合、その施用量は通常１０アールあたり５〜５
００２、乳剤、水和剤、フロアブル剤等を水で希釈して
施用する場合、その施用濃度は（１８）
１０〜２０００ ￥１１）ｍ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、家
庭、・防疫用殺虫、殺ダニ剤の有効成分として用いる場
合、乳剤、水和剤、フロアブル剤等は水で１０〜１０．
ＯＯＯｐｌ）ｍ に希釈して施用し、油剤、エアゾー
ル、燻蒸剤、燻煙剤、煙霧剤、ＵＬＶ剤、毒餌等につい
てはそのまま施用する。When compound CI) is used as an active ingredient in agricultural insecticides and acaricides, the application rate is usually 5 to 5 per 10 ares.
When applying 002, emulsions, wettable powders, flowables, etc. diluted with water, the application concentration is (18) 10 to 2000 yen 11) m, and granules, powders, etc. are not diluted in any way, Apply as is. In addition, when used as an active ingredient in insecticides and acaricides for household and epidemic prevention purposes, emulsions, wettable powders, flowable agents, etc. are mixed with water for 10 to 10 minutes.
Apply diluted to OOOpl)m, and apply as is for oils, aerosols, fumigants, smoke agents, fog agents, ULV agents, poison baits, etc.
これらの施用量、施用濃度は、いずれも製剤の種類、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
増加させたり、減少させたりすることができる。These application amounts and concentrations vary depending on the type of formulation, application time, application location, application method, type of pest, degree of damage, etc., and may be increased or decreased without regard to the above range. can do.
〈実施例〉
以下、本発明を参考例としての製造例、製剤例および試
験例により、さらに詳しく説明するが、本発明はこれら
の実施例に限定されるものではない。<Examples> Hereinafter, the present invention will be explained in more detail using production examples, formulation examples, and test examples as reference examples, but the present invention is not limited to these examples.
まず、化合物〔工〕の製造例を示す。First, an example of manufacturing the compound [technique] will be shown.
製造例（化合物番号（１）の製造
２．４．５−）リブロモイミダゾール（１，５８（１４
）
２．５ミリモル）、パラホルムアルデヒド（０，１５２
，５ミリモル）および無水酢酸（５ｍ／）の混合物を０
．１ Ｏｆのパラトルエンスルホン酸の共存下、１４０
〜１４５℃で５時間攪拌した。反応液を冷却後、減圧下
に濃縮し、得られた残留物をシリカゲルクロマトグラフ
ィーに付し、０．７２ｔの１−アセトキシメチル−２，
４，５−トリブロモイミタ′ゾールを得た。Production Example (Production of Compound No. (1) 2.4.5-) Ribromoimidazole (1,58(14
) 2.5 mmol), paraformaldehyde (0,152
, 5 mmol) and acetic anhydride (5 m/).
．． In the presence of 1 Of para-toluenesulfonic acid, 140
Stirred at ~145°C for 5 hours. After cooling the reaction solution, it was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 0.72 t of 1-acetoxymethyl-2,
4,5-tribromoimita'zole was obtained.
ｍ、１）、８６〜９０℃
このような製造法によって製造した化合物ＣＩ］のいく
つかを第１表に示す。m, 1), 86-90°C Some of the compounds CI produced by such a production method are shown in Table 1.
第 １ 表
一般式
で示されるトリバロイミ
ダゾール誘導体
（１７）
（１８）
次に製剤例を示す。なお、化合物〔ηは第１表に記載の
化合物番号で示し、部は重量部を表わす。Table 1 Trivaloimidazole derivatives (17) (18) represented by the general formulas (18) Next, formulation examples are shown. In addition, the compound [η is shown by the compound number described in Table 1, and parts represent parts by weight.
製剤例１ 乳剤
化合物（１）〜Ｇ９１の各々１０部を、キシレン８５部
お誹びジメチルホルムアミド８５部に溶解し、ポリオキ
シエチレンスチリルフェニルエーテル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。Formulation Example 1 10 parts each of Emulsion Compounds (1) to G91 were dissolved in 85 parts of xylene and 85 parts of dimethylformamide, 14 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate were added, and the mixture was thoroughly dissolved. Stir and mix to obtain each 10% emulsion.
製剤例２ 水和剤
化合物（１） 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部および珪礫土５４部を混合した中に加え
、ジュースミキサーで攪拌混合して２０％水和剤を得る
。Formulation Example 2 20 parts of wettable powder compound (1) were added to a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic hydrated silicon oxide fine powder, and 54 parts of diatomaceous earth, and mixed with a juice mixer. Stir and mix to obtain a 20% hydrating powder.
製剤例８ 粒剤
化合物（２） ５部に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部およびクレー６０部を
加え、充分攪拌混合する。ついで、これらの混合物に適
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５％粒剤を得る。Formulation Example 8 Add 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite, and 60 parts of clay to 5 parts of granule compound (2), and mix thoroughly with stirring. Then, an appropriate amount of water is added to the mixture, which is further stirred, granulated using a granulator, and dried through ventilation to obtain 5% granules.
製剤例４ 粉剤
化合物（３）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、Ｐ Ａ Ｐ ０．８部お
よびクレー９８．７部を加え、ジュースミキサーで攪拌
混合し、アセトンを蒸発除去して１％粉剤を得る。Formulation Example 4 Dissolve 1 part of powder compound (3) in an appropriate amount of acetone, add 5 parts of synthetic hydrated silicon oxide fine powder, 0.8 part of P A P and 98.7 parts of clay, and stir with a juice mixer. Mix and evaporate the acetone to obtain a 1% powder.
製剤例５７０アブル剤
化合物（４） １０部をポリビニルアルコール６部を含
む水溶液４０部中に加え、ミキサーで攪拌し、分散剤を
得る。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ート０．１部を含む水溶液
４０部を加え、さらに、プロピレングリコール１０部を
加えて緩やかに攪拌混合して１０％水中乳濁剤を得る。Formulation Example 570 10 parts of Able Compound (4) is added to 40 parts of an aqueous solution containing 6 parts of polyvinyl alcohol and stirred with a mixer to obtain a dispersant. To this, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate are added, and further, 10 parts of propylene glycol are added and mixed with gentle stirring to obtain a 10% emulsion in water.
製剤例６ 油剤
化合物（１）〜Ｃ１１ｌの各々０．１部をトリクロロエ
タン１０部に溶解し、これを灯油８９．９部に混合して
各々の０．１％油剤を得る。Formulation Example 6 Oil Agent 0.1 part of each of compounds (1) to C11l is dissolved in 10 parts of trichloroethane and mixed with 89.9 parts of kerosene to obtain each 0.1% oil agent.
製剤例７ 油性エアゾール
化合物（５） ０．１部、テトラメスリン０．２部、ｄ
フェノスリン０．１部、トリクロロエタン１０部および
灯油５９．６部を混合溶解し、エアゾール容器に充填し
、バルブ部分を取り付けた後、該バルブ部分全通じて噴
射剤（液化石油ガス）８０部を加圧充填して油性エアゾ
ールを得る。Formulation Example 7 Oil-based aerosol compound (5) 0.1 part, tetramethrin 0.2 part, d
Mix and dissolve 0.1 part of phenothrin, 10 parts of trichloroethane, and 59.6 parts of kerosene, fill it into an aerosol container, and attach the valve part, then add 80 parts of propellant (liquefied petroleum gas) throughout the valve part. Pressure filling to obtain an oil-based aerosol.
製剤例８ 蚊取線香
化合物（６） ０．８ ｆにｄ−アレスリン０．８２を
加え、アセトン２０−に溶解し、蚊取線香用担体（タブ
（２１）
粉：粕粉：木粉を４：８：８の割合で混合）９９．４２
と均一に攪拌混合した後、水１２０−を加え、充分練り
合せたものを成型乾燥して蚊取線香を得る。Formulation Example 8 Add 0.82 of d-allethrin to 0.8 f of mosquito coil compound (6), dissolve in 20 of acetone, and add 4 of mosquito coil carrier (tab (21) powder: lees powder: wood flour). : Mixed at a ratio of 8:8) 99.42
After stirring and mixing uniformly, 120% of water was added, and the mixture was thoroughly kneaded and dried to obtain a mosquito coil.
製剤例９ 加熱燻煙剤
化合物（１）〜Ｃ３Ｃの各々１００■を適量のアセトン
に溶解し、４． Ｑ ｃｍ Ｘ ４．０ ｃｍ 、厚さ
１．２ｍ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。Formulation Example 9 100 μm of each of heat smoke compound (1) to C3C was dissolved in an appropriate amount of acetone, and 4. Each hot smoke agent is obtained by impregnating a porous ceramic plate of Q cm x 4.0 cm and thickness of 1.2 m.
次に化合物〔ηが、殺虫、殺ダニ剤の有効成分として有
用であることを試験例により示す。なお、化合物α〕は
第１表の化合物番号で示し、比較対照に用いた化合物は
第２表の化合物記号で示す。Next, it will be shown by test examples that the compound [η] is useful as an active ingredient of insecticides and acaricides. Compound α] is indicated by the compound number in Table 1, and the compound used for comparison is indicated by the compound symbol in Table 2.
第２表
（２２）
試験例１
製剤例１に準じて得られた下記供試化合物の乳剤の、水
によるｉｏ 、 ｏｏｏ倍希釈液（１０ｐｐｍ）１００
ｒｎｌを１８０ｄポリカツプに入れ、その中にアカイ
エカ絡合幼虫２０頭を放飼した。餌を与えて飼育し、８
日後にその生死を調査し、死生率を求めた（２反復）。Table 2 (22) Test Example 1 An io, oooo fold dilution of an emulsion of the following test compound obtained according to Formulation Example 1 with water (10 ppm) 100
rnl was placed in a 180D polycup, and 20 Culex Culex entangled larvae were released therein. Feed and raise, 8
After 1 day, the animals were examined to see if they were alive or dead, and the mortality rate was determined (2 repetitions).
その結果を第８表に示す。The results are shown in Table 8.
＠３表
訃験例２
直径５．５（７）のポリエチレンカップの底に同大の濾
紙を敷き、製剤例１に準じて得られた供試化合物の乳剤
の、水による２００倍希釈液（５００ｐｐｍ）０、７
ｍｌを濾紙上に滴下し、餌としてショ糖３ｏｒｎ？を均
一に入れた。その中にピレスロイド低感受性系統のイエ
バエ雌成虫１０頭を放ち、蓋をして４８時間後にその生
死を調査し、死生率を求めた（２反復）。その結果を第
４表に示す。@3 Table Death Test Example 2 A filter paper of the same size was placed at the bottom of a polyethylene cup with a diameter of 5.5 (7), and a 200-fold dilution of the emulsion of the test compound obtained according to Formulation Example 1 with water ( 500ppm) 0,7
Drop ml onto filter paper and add 3 or 3 ml of sucrose as bait. was added evenly. Ten female adult houseflies of a pyrethroid-low-susceptibility strain were released into the container, and the container was covered with a lid. After 48 hours, their survival and death were determined to determine the mortality rate (two repetitions). The results are shown in Table 4.
第 ４ 表
試験例８
供試化合物の各々をアセトンで所定濃度（０１％Ｗ／Ｖ
）１２ｍ希釈し、チャバネゴキブリ雄成虫に対し、１頭
あたりその希釈液１μｌずつを胸部腹板上に局所施用し
、処理薬量が１μ２／頭となるようにした。処理後、供
試虫をポリエチレンカップ内に入れ、水と餌を与え、８
日後にその生死を調査し、死生率を求めた（１群１０頭
２反復）。その結果を第５表に示す。Table 4 Test Example 8 Each test compound was added to acetone at a predetermined concentration (01% W/V
) The diluted solution was diluted to 12 m, and 1 μl of the diluted solution per adult male German cockroach was locally applied to the thorax and abdominal plate so that the treatment dose was 1 μ2/head. After treatment, test insects were placed in a polyethylene cup, given water and food, and incubated for 8 hours.
A day later, the animals were examined to see if they were alive or dead, and the mortality rate was calculated (10 animals per group, 2 replicates). The results are shown in Table 5.
第 ５ 表
（２５）
試験例４
７０ｔＭ立方のガラスチャンバー（０，８４ｎｔ’）の
底部の４隅に、内側面にパターを塗布したポリエチレン
カップ（内径ＩＱａ＋＋、高さ８ｔＴｎ）を１つずつ計
４個設置し、それぞれのカップの中に、ピレスロイド低
感受性系統のチャバネゴキブリ成虫を雄ｌＯ頭２連、＃
１１０頭を２連となるように放飼した。チャンバーの中
央底部に電気加熱器を設置し、その上に製剤例９に準じ
て得られた供試化合物の多孔セラミック板マットの燻煙
剤（薬量１８．７■／マツト、４０η／♂）を置き、２
０分間通電し、約２００℃に加熱した。通電開始８０分
後、供試虫の入ったカップをチャンバーから取り出し、
水および餌を与え、２日後に生死数を調査し、死生率を
算出した（２反復）。Table 5 (25) Test Example 4 A total of 4 polyethylene cups (inner diameter IQa++, height 8tTn) with putter coated on the inner surface were placed in each of the four corners of the bottom of a 70tM cubic glass chamber (0.84nt'). In each cup, two adult German cockroaches of a pyrethroid-low susceptibility strain were placed, #
110 animals were released in duplicate. An electric heater was installed at the center bottom of the chamber, and on top of it was placed a porous ceramic plate mat smoking agent of the test compound obtained according to Formulation Example 9 (dose: 18.7■/mat, 40η/♂). and put 2
Electricity was applied for 0 minutes, and the mixture was heated to about 200°C. 80 minutes after the start of energization, the cup containing the test insect was removed from the chamber.
Water and food were given, and the number of living and dead animals was investigated two days later, and the mortality rate was calculated (two repetitions).
その結果を第６表に示す。The results are shown in Table 6.
（２６）
第
６
表
試験例５
播種７日後の鉢植ツルナシインゲン（初生葉期）に、−
葉当り１０頭のニセナミハダこの雌成虫を寄生させ、２
５℃の恒温室に置いた。６日後、製剤例１に準じて得ら
れた供試化合物の乳剤の、水による２００倍希釈液（５
００ｐｐｍ）を、ターン（２７）
テーブル上で１鉢当り１５ｍ１散布し、同時に同波２−
を土壌漸注した。８日後にそれぞれの植物のハダニによ
る被害程度を調査した（２反復）。効果判定基準は
：はとんど被害が認められない。(26) Table 6 Test Example 5 -
Each leaf is infested with 10 female adults of Nisenamida, and 2
It was placed in a constant temperature room at 5°C. After 6 days, the emulsion of the test compound obtained according to Formulation Example 1 was diluted 200 times with water (5
Spray 15ml of 00ppm) per pot on the turn (27) table, and at the same time spray 2-
was injected into the soil. After 8 days, the degree of damage caused by spider mites on each plant was investigated (2 repetitions). Criteria for evaluating effectiveness: Almost no damage is observed.
＋：少し被害が認められる。+: Slight damage is observed.
＋：無処理区と同様の被害が認められる。+: The same damage as in the untreated area is observed.
とじた。その結果を第７表に示す。Closed. The results are shown in Table 7.
第 ７ 表 虫、 双翅目害虫等の各種害虫類や、 ハダニ類等の 有害ダニ類に対し優れた殺虫、 殺ダニ効力を示す。Table 7 insect, Various pests such as Diptera pests, Spider mites, etc. Excellent insecticide against harmful mites, Shows acaricidal efficacy.
（２９完）(29 completed)
Claims (2)
基、アルケニル基、フリル基、フェニル基、置換フェニ
ル基、シクロアルキル基、ビシクロアルケニル基または
チエニル基を表わし、Ｒ＾２はアルキル基、アルケニル
基、ハロアルキル基またはシクロアルキル基を表わす。 〕 で示されるトリハロイミダゾール誘導体を有効成分とし
て含有することを特徴とする殺虫、殺ダニ剤。(1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R^1 is a hydrogen atom, an alkyl group, a substituted alkyl group, an alkenyl group, a furyl group, a phenyl group, a substituted phenyl group, a cycloalkyl group, It represents a bicycloalkenyl group or a thienyl group, and R^2 represents an alkyl group, an alkenyl group, a haloalkyl group or a cycloalkyl group. ] An insecticide and acaricide characterized by containing a trihaloimidazole derivative shown as an active ingredient.
いる殺虫、殺ダニ方法。(2) An insecticidal or acaricidal method using the trihaloimidazole derivative according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2771090A JPH03232805A (en) | 1990-02-06 | 1990-02-06 | Use of trihaloimidazole derivative as insecticide and acaricide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2771090A JPH03232805A (en) | 1990-02-06 | 1990-02-06 | Use of trihaloimidazole derivative as insecticide and acaricide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03232805A true JPH03232805A (en) | 1991-10-16 |
Family
ID=12228556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2771090A Pending JPH03232805A (en) | 1990-02-06 | 1990-02-06 | Use of trihaloimidazole derivative as insecticide and acaricide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03232805A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013516466A (en) * | 2010-01-07 | 2013-05-13 | アルカーメス ファーマ アイルランド リミテッド | Prodrugs of heteroaromatic compounds |
-
1990
- 1990-02-06 JP JP2771090A patent/JPH03232805A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013516466A (en) * | 2010-01-07 | 2013-05-13 | アルカーメス ファーマ アイルランド リミテッド | Prodrugs of heteroaromatic compounds |
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