JPS60116601A - Mixed insecticidal composition - Google Patents

Mixed insecticidal composition

Info

Publication number
JPS60116601A
JPS60116601A JP22661683A JP22661683A JPS60116601A JP S60116601 A JPS60116601 A JP S60116601A JP 22661683 A JP22661683 A JP 22661683A JP 22661683 A JP22661683 A JP 22661683A JP S60116601 A JPS60116601 A JP S60116601A
Authority
JP
Japan
Prior art keywords
group
carbon atoms
ether derivative
integer
atom
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
Application number
JP22661683A
Other languages
Japanese (ja)
Inventor
Makoto Hatagoshi
波多腰 信
Tadashi Osumi
大住 忠司
Hiroshi Kishida
博 岸田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to JP22661683A priority Critical patent/JPS60116601A/en
Publication of JPS60116601A publication Critical patent/JPS60116601A/en
Pending legal-status Critical Current

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Abstract

PURPOSE:The titled composition, containing a specific oxime ether derivative and an ether derivative as active constituents, capable of exhibiting improved effect of controlling larvae and imagoes of injurious insetcs by synergistic effect at the same time, and reducing the imago density having the fecundity. CONSTITUTION:A mixed insecticidal composition containing an oxime ether derivative of formula I (R1 and R2 are H, 1-3C alkyl or 1-3C alkyl substituted by halogen, 2-3C alkoxyalkyl, etc.; R3 and R4 are H or CH3; R5 is CH3 or halogen; R6 is 1-4C alkyl, methoxyl, halogen, etc.; X is O, S or methylene; Y is O or S; l is an integer 0-5; m is an integer 0-4; n is an integer 0-2) having the well-known remarkable controlling effect on mosquitoes, larvae, housefly larvae, et. and an ether derivative of formula II [Ar is aryl; R is CH3 or C2H5; B is furmula III or IV (Z is O, S, -CO- or NH-; R' is H, halogen, lower alkyl or lower alkoyl; n' is an integer 1-5)] having the well-known insecticidal activity.

Description

【発明の詳細な説明】 本発明は、一般式(I) 〔式中、R1およびR2は同一または相異なり、水素原
子、炭素原子数1〜8のアIし炭素原子数2〜8を含む
アルコキシアルキル基、炭素原子数2〜3のアルケニル
基、炭素原子数2〜4のアルキニル基、炭素原子数1〜
2のアルキルチオ基、フェニル基、ピリジル基、フリル
基またはチェニル基を表わす。さらにR1とR2とが末
端で結合することにより、酸素原子または硫黄原子を0
〜2個環内に含む飽和または不飽和の5員環もしくは6
員環を形成することができる。N、お転びR4は同一ま
たは相異なり、水素原子またはメチル基を表わし、RI
Iはメチル基またはハロゲン原子を表わし、艮。は炭素
原子数1〜4のアノレキIし基、メトキシ基、ハロゲン
原子、トリフIレオロメチル基またはニトロ基を表わし
、Xは酸素原子、硫黄原子またはメチレン基を表わし、
Yは酸素原子または硫黄原子を表わし、eはO〜5の、
mは0−4の、nはθ〜2の整数をそれぞれ表わす。〕 で示されるオキシムエーテIし誘導体と一般式〔式中、
Ar はアリ−Iし基を表わし、Kはメチル基またはエ
チル基を表わし、Bは一般式 (式中、2は酸素原子、イオウ原子’、 −CO−基ま
たは−NH−基を表わし、λ′は水素原子、ハロゲン原
子、低級アルキjし基または低級アルコキシ基を表わし
、n′は1〜5の整数を表わす。ただし、n′≧2のと
きは、k′は同一または相異なる基を表わす。)で表わ
される基を表わす。〕 で示されるエーテル誘導体とを含有することを特徴とす
る混合殺虫組成物である。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to compounds of the general formula (I) [wherein R1 and R2 are the same or different and contain a hydrogen atom, a carbon atom number of 1 to 8, and a carbon atom number of 2 to 8] Alkoxyalkyl group, alkenyl group having 2 to 3 carbon atoms, alkynyl group having 2 to 4 carbon atoms, 1 to 3 carbon atoms
2 represents an alkylthio group, phenyl group, pyridyl group, furyl group or chenyl group. Furthermore, by bonding R1 and R2 at the terminal, oxygen or sulfur atoms can be reduced to 0.
~2 saturated or unsaturated 5-membered or 6-membered rings contained within the ring
Can form a membered ring. N, and R4 are the same or different and represent a hydrogen atom or a methyl group, and RI
I represents a methyl group or a halogen atom; represents an anorexic group having 1 to 4 carbon atoms, a methoxy group, a halogen atom, a trifluoromethyl group or a nitro group, and X represents an oxygen atom, a sulfur atom or a methylene group,
Y represents an oxygen atom or a sulfur atom, e is O~5,
m represents an integer from 0 to 4, and n represents an integer from θ to 2. ] An oximeate I derivative represented by the general formula [wherein,
Ar represents an aryl group, K represents a methyl group or an ethyl group, and B represents a general formula (wherein 2 represents an oxygen atom, a sulfur atom', a -CO- group or an -NH- group, and λ ' represents a hydrogen atom, a halogen atom, a lower alkyl group, or a lower alkoxy group, and n' represents an integer of 1 to 5. However, when n'≧2, k' represents the same or different groups. represents a group represented by ). ] This is a mixed insecticidal composition characterized by containing an ether derivative represented by the following.

一般式(I)で示されるオキシムエーテル誘導体が蚊幼
虫、イエバエ幼虫等に対し卓効した防除効果を有するこ
とは、特開昭58−150559号公報に記載されてお
り、公知の事実である。
It is a well-known fact that the oxime ether derivative represented by the general formula (I) has an excellent control effect on mosquito larvae, house fly larvae, etc., as described in JP-A-58-150559.

また、一般式((I)で示されるエーテル誘導体が殺虫
活性を有することは、仏国特杆第8108642号明細
書に記載されており、公知の事実である。しかし、一般
式(Ilで示されるオキシムエーテル誘導体は成虫防除
に対しては、その効果はきわめて低く、また、−般式(
ロ)で示されるエーテル誘導体の幼虫に対する効果は充
分満足すべきものではない。 。
Furthermore, it is a well-known fact that the ether derivative represented by the general formula (I) has insecticidal activity, as described in the specification of FR No. 8108642. The oxime ether derivatives used in this study have extremely low effectiveness in controlling adult insects, and also have the general formula (
The effect of the ether derivative shown in b) on larvae is not fully satisfactory. .

本発明者らは、幼虫、・成虫同時防除を目的として鋭怠
検討した結果、作用性の異なる有害生物防除剤と殺虫剤
とを混合して得られる混合剤を処理することによって、
害虫の幼虫および成虫に作用し、結果的に生殖能力を持
つ成虫密度を低下させ得る殺虫混合組成物を見出した。
As a result of intensive research aimed at simultaneous control of larvae and adults, the present inventors discovered that by treating a mixture obtained by mixing pest control agents and insecticides with different activities,
We have found an insecticidal mixture composition that acts on larvae and adults of pests and can consequently reduce the density of reproductive adults.

本発明組成物は、ウンカ・ヨコバイ類、コカジラミ類、
アブラムシ類、カメムシ類、カイがラムシ類などの半翅
目、シロアリ類などの等翅目、アリ類、ハバチ類などの
膜翅目、コナが、二カメイが、ヨトウ類などの+4翅目
、アカイエカ、イエバエなどの双翅目、チャバネゴキブ
リな′どの網翅目、タバコシバンムシ、アズキゾウムシ
などの鞘翅目および直翅目などの害虫に有効である。
The composition of the present invention includes planthoppers, leafhoppers, bodyflies,
Hemiptera such as aphids, stink bugs, and caterpillars; Isoptera such as termites; Hymenoptera such as ants and wasps; It is effective against pests such as Diptera such as Culex mosquito and house fly, Reciptera such as German cockroach, Coleoptera such as tobacco beetle and bean weevil, and Orthoptera.

本発明でいう一般式tI)で示されるオキシムエーテル
誘導体および一般式([I)で示されるエーテル誘導体
としては、たとえば次のものをあげることができるが、
これによって本発明が限定されるものでないことは言う
までもない。なお、オキシムエーテル誘導体にはR2お
よびR,に基づく光学異性体ならびにR4およびR5に
基づく幾何異性体が存在するが、これらも全て本発明に
含まれることは言うまでもない。
Examples of the oxime ether derivative represented by the general formula tI) and the ether derivative represented by the general formula ([I) in the present invention include the following:
It goes without saying that the present invention is not limited by this. Incidentally, the oxime ether derivative includes optical isomers based on R2 and R, and geometric isomers based on R4 and R5, and it goes without saying that all of these are included in the present invention.

表1 一般式(月 のオキシムエーテル誘導体 表2 1 に のエーテル誘導体 本発明組成物を殺虫剤として用いる場合は、常、固体担
体、液体担体、界面活性剤、そ池の製剤用補助剤と混合
して、乳剤、水和剤、油剤、粉剤等に製剤する。
Table 1 Ether derivatives with the general formula (oxime ether derivatives Table 2 1) When the composition of the present invention is used as an insecticide, it is usually mixed with a solid carrier, a liquid carrier, a surfactant, and other formulation auxiliaries. and formulate emulsions, wettable powders, oils, powders, etc.

各製剤には、有効成分としてオキシムエーテル誘導体と
エーテル誘導体とを重量比で01〜99%含有すること
ができ、またオンムエーテル誘導体とエーテル誘導体と
の合比は1:20〜20:1が適当である。
Each preparation can contain an oxime ether derivative and an ether derivative in a weight ratio of 01 to 99% as active ingredients, and the appropriate ratio of the oxime ether derivative to the ether derivative is 1:20 to 20:1. be.

これらの製剤は常法に従って調整することできる。この
場合固体担体としては、粘土(たとえばカオリン、ベン
トナイト、酸自土、ピロフィライト、セリサイト)、タ
フ類、その他無機鉱物(たとえば水和二酸アイ素、軽石
、珪藻土、硫黄粉末、活性炭)どの微粉末ないし粉状物
があげられる。
These formulations can be prepared according to conventional methods. In this case, solid carriers include clays (e.g. kaolin, bentonite, acid earth, pyrophyllite, sericite), tuffs, other inorganic minerals (e.g. hydrated iron dioxide, pumice, diatomaceous earth, sulfur powder, activated carbon), etc. Powder or pulverulent materials can be mentioned.

【体担体としては、アルコール類(たとえエチルアルコ
ール、エチルアルコール)、−ン類(たとえばアセトン
、メチルエチルーン)、エーテル類(たとえばエチルエ
ーチル、ジオキサン、セロソルブ、テトラハイドロフラ
ン)、芳香族炭化水素類(たとえばベンゼン、トルエン
、キシレン、メチルナフタレン)、脂肪族炭化水素類(
たとえばがンリーン、ケロシン、灯油)、エステル類、
ニトリル類、酸アミド類(たとえばメチルホルムアミド
、ジメチルアセタマイド)、ハロゲン化炭化水素類(た
とえばジクロロエタン、トリクロロエチレン、四塩化炭
素)などがあげられる。次に界面活性剤としては、アル
キル硫酸エステル類、アルキルスルホン酸塩、アルキル
アリールスルホン酸塩、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などがあげられる。ま
た、使用できる固着剤や分散剤としては、カゼイン、ゼ
ラチン、でんぷん粉、CMC,アラビヤゴム、アルギン
酸、リクニンスルフォネート、ベントナイト、糖蜜、ポ
リビニルアルコール、松根油、寒天などがあり、安定剤
としては、たとえばPAP (リン酸インプロピル)、
Tcp(トリクレジルホスフェート)、トール油、エポ
キシ化油、各種界面活性剤、各種脂肪酸またはそのエス
テルなどがあげられる。
[Carriers include alcohols (such as ethyl alcohol and ethyl alcohol), -ones (such as acetone and methylethylone), ethers (such as ethyl ethyl, dioxane, cellosolve, and tetrahydrofuran), aromatic hydrocarbons (such as ethyl ethyl, dioxane, cellosolve, and tetrahydrofuran), For example, benzene, toluene, xylene, methylnaphthalene), aliphatic hydrocarbons (
For example, ganlene, kerosene, kerosene), esters,
Nitriles, acid amides (for example, methylformamide, dimethylacetamide), halogenated hydrocarbons (for example, dichloroethane, trichloroethylene, carbon tetrachloride), and the like. Examples of surfactants include alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, polyethylene glycol ethers, and polyhydric alcohol esters. Fixing agents and dispersing agents that can be used include casein, gelatin, starch powder, CMC, gum arabic, alginic acid, likunin sulfonate, bentonite, molasses, polyvinyl alcohol, pine oil, agar, etc., and stabilizers include , for example PAP (impropyl phosphate),
Examples include Tcp (tricresyl phosphate), tall oil, epoxidized oil, various surfactants, and various fatty acids or esters thereof.

次にいくつかの製剤例および試験例を示すが、本発明は
もちろんこれらのみに限定されるものではない。
Next, some formulation examples and test examples will be shown, but the present invention is of course not limited to these.

製剤例1 オキシムエーテル誘導体(2110部、エーテル誘導体
(VIIO部、乳化剤(ポリオキシエチレンスチレン化
フェニルエーテル、ポリオキシエチレンスチレン化フェ
ニルエーテルのポリマー、アルキルアリールスルホン酸
塩の混合物)20部およびキシレン60部を加え、これ
らをよく攪拌混合すれば乳剤を得る。
Formulation Example 1 Oxime ether derivative (2110 parts, ether derivative (VIIO part), 20 parts of emulsifier (polyoxyethylene styrenated phenyl ether, polyoxyethylene styrenated phenyl ether polymer, mixture of alkylaryl sulfonate) and 60 parts of xylene. and stir well to obtain an emulsion.

製剤例2 オキシムエーテル誘導体(29) 5部とエーテル誘導
体(ill 10部に乳化剤(ラウリル硫酸ナトリウム
)51部をよ(混合し、800メツシユ珪藻土8.0部
を加え、擢漬器中にて充分攪拌混合すれば水和剤を得る
Formulation Example 2 Mix 5 parts of oxime ether derivative (29) and 10 parts of ether derivative (ill) with 51 parts of emulsifier (sodium lauryl sulfate), add 8.0 parts of 800 mesh diatomaceous earth, and stir thoroughly in a pickler. Mixing yields a hydrating agent.

製剤例8 オキシムエーテル誘導体(5)1部とエーテル誘導体位
)1部とをアセトン20部に溶解し、800メツシュタ
ルク98部を加え、播演器中にて充分攪拌混合した後、
アセトンを蒸発除去すれば粉剤を得る。
Formulation Example 8 1 part of oxime ether derivative (5) and 1 part of ether derivative position) were dissolved in 20 parts of acetone, 98 parts of 800 Metsstarck were added, and after thorough stirring and mixing in a spreader,
A powder is obtained by removing the acetone by evaporation.

製剤例4 全体を100部とすれば油剤を得る。Formulation example 4 If the total is 100 parts, an oil solution is obtained.

試験例1 イエバエ成虫の雌雄各50頭をケージに入れた。一方、
フスマ14t、粉末藺料2tおよび水28g/を充分混
合し、こうしてできたイエバエ用人工培地にイエバエ4
日令幼虫30顧を放った。オキシムエーテル語導体(2
9)の20%乳剤〔オキシムエーテル誘導体(29)2
0部に乳化剤(ポリオキシエチレンスチレン化フェニル
エーテル、ポリオキシエチレンスチレン化フェニルエー
テルのポリマーおよびアルキルアリールスルホン酸塩の
混合物)20部およびキシレン60部を加え、これらを
よく攪拌混合して得た。〕を水で所定濃度に希釈した。
Test Example 1 Fifty male and female adult house flies were placed in a cage. on the other hand,
Thoroughly mix 14 tons of wheat bran, 2 tons of powdered wheat, and 28 g of water, and place 4 house flies in the artificial medium for house flies.
Thirty day old larvae were released. Oxime etheric conductor (2
9) 20% emulsion [oxime ether derivative (29) 2
20 parts of an emulsifier (a mixture of polyoxyethylene styrenated phenyl ether, a polymer of polyoxyethylene styrenated phenyl ether, and an alkylaryl sulfonate) and 60 parts of xylene were added to 0 parts, and these were thoroughly stirred and mixed. ] was diluted with water to a predetermined concentration.

同様にしてエーテル誘導体(l/ilの20%乳剤を製
剤し、水で所定濃度に希釈した。一方、水で所定濃度に
希釈した各化合物液を混合して混合剤を調整した。この
混合剤および各単剤をイエバエ成虫の入ったケージとイ
エバエ成虫の入った容器にそれぞれ20耐散布した。散
布後、イエバエ幼虫の入った容器を同一薬剤を処理した
成虫ケージに入れ、以後ケージ内の成虫数を調査した。
Similarly, a 20% emulsion of ether derivative (l/il) was prepared and diluted with water to a predetermined concentration.Meanwhile, a mixture was prepared by mixing each compound solution diluted with water to a predetermined concentration.This mixture Each single agent was sprayed for 20 hours each into a cage containing adult house flies and a container containing adult house flies.After spraying, the container containing house fly larvae was placed in an adult cage treated with the same agent, and from then on, adults in the cage were I investigated the numbers.

結果は補正密度指数として次式にようだ。結 ・果を表
8に示す。
The result is the corrected density index as shown in the following equation. Results - The results are shown in Table 8.

第1頁の続きContinuation of page 1

Claims (1)

【特許請求の範囲】 下記一般式tI)で示されるオキシムエーテル誘導体と
一般式((I)で示されるエーテル誘導体とを有効成分
として含有することを特徴とする混合殺虫組成物。 〔式中、Klおよび艮、は同−韮たは相異なり、水素原
子、炭素原子数1〜8のアルキル基、炭素原子数1〜8
の部分的または全部がハロゲン原子で置換されたアルキ
ル基、炭素原子数2〜8を含むアルコキシアルキル基、
炭素原子数2〜8のアルケニル基、炭素原子数2〜4の
アルキニル基、炭素原子数1〜2のアルキルチオ基、フ
ェニル基、ピリジル基、フルル基またはチェニIし基を
表わす。さらにR1とR,とが末端で結合することによ
り、酸素原子または硫黄原子を0〜2個環内に含む飽和
または不飽和の5員環もしくは6員環を形成することが
できる。RIおよびR4は同一または相異なり、水素原
子またはメチル基を表わし、R6はメチル基またはハロ
ゲン原子を表わし、R6は炭素原子数1〜4のアルキル
基、メトキシ基、ハロゲン原子、トリフlレオロンチル
基またはニトロ基を表わし、Xは酸素原子、硫黄原子ま
たはメチレン基を表わし、Yは酸素原子または硫黄原子
を表わし、eは0〜5の、mはθ〜4の、nは0〜2の
整数をそれぞれ表わす。〕 1 艮 〔式中、Ar はアリール基を表わし、kはメチル基ま
たはエチル基を表わし、Bは一般式 (式中、Zは酸素原子、イオウ原子、−CO−基または
−NH−基を表わし、λ′は水素原子、ハロゲン原子、
低級アルキル基または低級アルコキシ基を表わし、n′
は1〜5の整数を表わす。ただし、n’a2のときは、
艮′は同一または相異なる基を表わす。)で表わされる
基を表わす。〕
[Scope of Claims] A mixed insecticidal composition characterized by containing an oxime ether derivative represented by the following general formula tI) and an ether derivative represented by the general formula ((I)) as active ingredients. Kl and 艮 are the same or different, hydrogen atom, alkyl group having 1 to 8 carbon atoms, 1 to 8 carbon atoms
an alkyl group partially or entirely substituted with a halogen atom, an alkoxyalkyl group containing 2 to 8 carbon atoms,
It represents an alkenyl group having 2 to 8 carbon atoms, an alkynyl group having 2 to 4 carbon atoms, an alkylthio group having 1 to 2 carbon atoms, a phenyl group, a pyridyl group, a furyl group, or a Chenyl group. Further, by bonding R1 and R at the terminals, a saturated or unsaturated 5- or 6-membered ring containing 0 to 2 oxygen atoms or sulfur atoms in the ring can be formed. RI and R4 are the same or different and represent a hydrogen atom or a methyl group, R6 represents a methyl group or a halogen atom, and R6 is an alkyl group having 1 to 4 carbon atoms, a methoxy group, a halogen atom, a trifluorontyl group, or represents a nitro group; Represent each. ] 1 [In the formula, Ar represents an aryl group, k represents a methyl group or an ethyl group, and B represents a general formula (wherein, Z represents an oxygen atom, a sulfur atom, a -CO- group or a -NH- group) where λ′ is a hydrogen atom, a halogen atom,
Represents a lower alkyl group or lower alkoxy group, n'
represents an integer from 1 to 5. However, when n'a2,
艮′ represents the same or different groups. ) represents a group represented by ]
JP22661683A 1983-11-29 1983-11-29 Mixed insecticidal composition Pending JPS60116601A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP22661683A JPS60116601A (en) 1983-11-29 1983-11-29 Mixed insecticidal composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP22661683A JPS60116601A (en) 1983-11-29 1983-11-29 Mixed insecticidal composition

Publications (1)

Publication Number Publication Date
JPS60116601A true JPS60116601A (en) 1985-06-24

Family

ID=16847993

Family Applications (1)

Application Number Title Priority Date Filing Date
JP22661683A Pending JPS60116601A (en) 1983-11-29 1983-11-29 Mixed insecticidal composition

Country Status (1)

Country Link
JP (1) JPS60116601A (en)

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