JPH04360804A - Insecticidal and fungicidal composition for agricultural and horticultural use - Google Patents

Insecticidal and fungicidal composition for agricultural and horticultural use

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Publication number
JPH04360804A
JPH04360804A JP15969091A JP15969091A JPH04360804A JP H04360804 A JPH04360804 A JP H04360804A JP 15969091 A JP15969091 A JP 15969091A JP 15969091 A JP15969091 A JP 15969091A JP H04360804 A JPH04360804 A JP H04360804A
Authority
JP
Japan
Prior art keywords
group
insecticidal
substituted
agricultural
triflumizole
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.)
Granted
Application number
JP15969091A
Other languages
Japanese (ja)
Other versions
JP2990865B2 (en
Inventor
Michihiko Matsuda
松田 逵彦
Nobuo Takakusa
高草 伸生
Atsushi Yamamoto
敦司 山本
Takao Iwasa
孝男 岩佐
Akira Hashimoto
章 橋本
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.)
Nippon Soda Co Ltd
Original Assignee
Nippon Soda 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 Nippon Soda Co Ltd filed Critical Nippon Soda Co Ltd
Priority to JP3159690A priority Critical patent/JP2990865B2/en
Priority to PCT/JP1992/000714 priority patent/WO1992021241A1/en
Publication of JPH04360804A publication Critical patent/JPH04360804A/en
Application granted granted Critical
Publication of JP2990865B2 publication Critical patent/JP2990865B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Abstract

PURPOSE:To obtain an insecticidal and fungicidal composition for agricultural and horticultural use, exhibiting synergistic action to increase the effect compared with the separate use of the components, free from phytotoxicity to crops and having low toxicity to warm-blooded animals by using a specific amine derivative in combination with triflumizole. CONSTITUTION:The objective insecticidal and fungicidal composition for agricultural and horticultural use exhibiting synergistic insecticidal and fungicidal actions to major blights of paddy rice, fruit trees, vegetables, barley, etc., such as planthopper, leafhopper, aphid, diamondback moth, downy mildew and scab can be produced by compounding (A) a compound of formula [R1 is (substituted) pyridyl, pyrazyl or thiazolyl except for unsubstituted 2-pyridyl; X is (substituted) alkylene or alkylidene; R2 and R3 are H, (substituted) alkyl or cycloalkyl; R2 may be alkenyl, alkynyl or YR5; Y is O or CO; R5 is (substituted) alkyl or aryl; R4 is CN or NO2] or its salt and (B) triflumizole at a weight ratio (A:B) of 1:(1-20).

Description

【発明の詳細な説明】[Detailed description of the invention]

【0001】0001

【産業上の利用分野】本発明は後記式〔I〕のアミン誘
導体とトリフルミゾールとの組合せからなる優れた殺虫
殺菌効果を有する新規な農園芸用殺虫殺菌組成物に関す
る。
BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel insecticidal and fungicidal composition for agricultural and horticultural use, which has an excellent insecticidal and fungicidal effect and is composed of a combination of an amine derivative of the formula [I] below and triflumizole.

【0002】0002

【従来の技術】農園芸作物の栽培に当り、作物の病虫害
に対して多数の防除薬剤が使用されているが、その防除
効力が不十分であったり、薬剤抵抗性の害虫や病原菌の
出現によりその使用が制限されたり、また植物体に薬害
や汚染を生じたり、あるいは人畜魚類などに対する毒性
が強かったりすることから、必ずしも満足すべき防除薬
剤とは言い難いものが少なくない。従って、かかる欠点
の少ない安全に使用できる薬剤の開発が強く要望されて
いる。
[Prior Art] In the cultivation of agricultural and horticultural crops, a large number of pesticides are used to control crop pests and diseases. Many of them are not necessarily satisfactory pesticidal agents because their use is limited, they cause phytotoxicity or contamination of plants, or they are highly toxic to animals, animals, and fish. Therefore, there is a strong demand for the development of drugs that are free from such drawbacks and can be used safely.

【0003】0003

【発明が解決しようとする課題】本発明者らは、後記式
〔I〕で表わされるアミン誘導体のより有効な利用を検
討する中で、トリフルミゾールとの組合せを研究した結
果、共力的な殺虫効果および殺菌効果が得られることを
見出した。
[Problems to be Solved by the Invention] While considering the more effective use of the amine derivative represented by the formula [I] below, the present inventors investigated the combination with triflumizole and found that synergistic It has been found that a significant insecticidal and bactericidal effect can be obtained.

【0004】0004

【課題を解決するための手段】本発明は、一般式〔I〕
[Means for Solving the Problems] The present invention provides general formula [I]

【化2】 {式中、R1 は無置換2−ピリジル基を除く、置換さ
れていてもよいピリジル基、ピラジル基又はチアゾリル
基を、Xは置換されていてもよいアルキレン基又はアル
キリデン基を、R2 は水素原子、置換されていてもよ
いアルキル基、アルケニル基、アルキニル基、シクロア
ルキル基、シクロアルケニル基もしくはアリール基、又
はY−R5 を、Yは酸素原子、−CO−を、R5 は
置換されていてもよいアルキル基もしくはアリール基を
、R3 は水素原子、置換されていてもよいアルキル基
、シクロアルキル基を、R4 はシアノ基又はニトロ基
を示す。}で表わされる化合物又はその塩およびトリフ
ルミゾールを含有する農園芸用殺虫殺菌組成物であり、
新規な活性物質の組合せが優れた殺虫効果および殺菌効
果を示すことが見出された。
[Formula 2] {wherein R1 is an optionally substituted pyridyl group, pyrazyl group, or thiazolyl group, excluding an unsubstituted 2-pyridyl group, and X is an optionally substituted alkylene group or alkylidene group, R2 is a hydrogen atom, an optionally substituted alkyl group, alkenyl group, alkynyl group, cycloalkyl group, cycloalkenyl group, or aryl group, or Y-R5, Y is an oxygen atom, -CO-, R5 is a substituted R3 represents a hydrogen atom, an optionally substituted alkyl group or cycloalkyl group, and R4 represents a cyano group or a nitro group. } or a salt thereof and triflumizole, an agricultural and horticultural insecticidal and bactericidal composition,
It has been found that the new active substance combination exhibits excellent insecticidal and fungicidal effects.

【0005】前記式〔I〕のアミン誘導体又はその塩に
トリフルミゾールを配合した本発明による殺虫殺菌組成
物の殺虫効果および殺菌効果はそれぞれ単独の活性化合
物の効果より大であり、優れた共力作用を示した。即ち
、本発明による殺虫殺菌組成物を施用することにより、
例えば水稲の重要病害虫であるウンカ、ヨコバイ類、い
もち病、例えば果樹、野菜等の重要病害虫であるアブラ
ムシ、コナガ、ハマキムシ、べと病、黒星病、例えば麦
の重要病害虫であるアブラムシやうどんこ病に対して各
々単独の活性化合物のみの場合より効果が大で、共力的
な殺虫および殺菌効果を示した。
The insecticidal and fungicidal compositions of the present invention, which contain the amine derivative of formula [I] or its salt and triflumizole, have greater insecticidal and fungicidal effects than those of the active compound alone, and have excellent synergistic effects. It showed force action. That is, by applying the insecticidal and fungicidal composition according to the present invention,
For example, important pests of paddy rice such as planthoppers, leafhoppers, and blast disease; important pests of fruit trees and vegetables such as aphids, diamondback moths, leaf beetles, downy mildew, and scab; important pests of wheat such as aphids and powdery mildew. The effect was greater than that of each active compound alone, and showed a synergistic insecticidal and fungicidal effect.

【0006】昆虫細胞内のミクロゾーム分画に存在する
酵素チトクロームP−450は、体内へ侵入する薬物を
酸化的に解毒することが知られている(池庄司ら、昆虫
生理、生化学、朝倉書店、230、1986年)。この
チトクロームP−450を阻害するトリフルミゾール〔
中山ら、日本農薬学会誌14(1)、23−37、19
89)〕が一般式〔I〕のアミン誘導体の昆虫体内での
代謝に作用して共力効果を発揮しているものと考えられ
る。
[0006] The enzyme cytochrome P-450, which exists in the microsomal fraction within insect cells, is known to oxidatively detoxify drugs that enter the body (Shoji Ike et al., Insect Physiology, Biochemistry, Asakura Shoten; 230, 1986). Triflumizole [which inhibits this cytochrome P-450]
Nakayama et al., Journal of the Japanese Society of Pesticides 14(1), 23-37, 19
89)] is thought to exert a synergistic effect by acting on the metabolism of the amine derivative of general formula [I] in the insect body.

【0007】本発明による活性物質組み合せにおいて使
用される好ましい一般式〔I〕のアミン誘導体は下記の
ごとく定義される。
Preferred amine derivatives of the general formula [I] used in the active substance combinations according to the invention are defined as follows.

【化3】 式中、R1 は無置換2−ピリジル基を除く、クロル原
子等のハロゲン原子、シアノ基又は低級ハロアルキル基
で置換されたピリジル基、又はクロル原子等のハロゲン
原子で置換されたピラジル基、又はクロル原子等のハロ
ゲン原子及びメチル基より選ばれる1つ又は2つで置換
されたチアゾリル基を、Xはメチレン基を、R2 は水
素原子、低級アルキル基、シアノ基で置換されたアルキ
ル基、アリル基、プロパギル基、シクロプロピル基、低
級アルコキシ基、メトキシメチル基、メチルチオメチル
基、クロル原子で置換されてもよいベンジル基、クロル
原子で置換されたピリジルメチル基、クロル原子で置換
されたピリジルエチル基、アセチル基又はクロル原子で
置換されたベンゾイル基を、R3 は水素原子、クロル
原子やフッ素原子等ハロゲン原子で置換されていても良
い低級アルキル基又はシクロプロピル基、R4 はシア
ノ基又はニトロ基を表わす。
[Formula 3] In the formula, R1 is a halogen atom such as a chlor atom, a pyridyl group substituted with a cyano group or a lower haloalkyl group, or a pyrazyl substituted with a halogen atom such as a chloro atom, excluding an unsubstituted 2-pyridyl group. or a thiazolyl group substituted with one or two selected from a halogen atom such as a chlorine atom and a methyl group, X is a methylene group, and R2 is an alkyl substituted with a hydrogen atom, a lower alkyl group, or a cyano group. group, allyl group, propargyl group, cyclopropyl group, lower alkoxy group, methoxymethyl group, methylthiomethyl group, benzyl group optionally substituted with chlorine atom, pyridylmethyl group substituted with chlorine atom, R3 is a hydrogen atom, a lower alkyl group optionally substituted with a halogen atom such as a chlorine atom or a fluorine atom, or a cyclopropyl group, and R4 is a cyano group. Or represents a nitro group.

【0008】本発明による活性物質組合せにおいて使用
される一般式〔I〕のアミン誘導体の例として次の第1
表に示す化合物が挙げられる。下記アミン誘導体又はそ
の塩製造方法及びそれらの殺虫剤としての使用は、WO
91/04965に記載されている。
Examples of amine derivatives of general formula [I] used in the active substance combination according to the invention include the following
Examples include the compounds shown in the table. The following amine derivatives or their salt production methods and their use as insecticides are described in WO
No. 91/04965.

【0009】[0009]

【表101】[Table 101]

【0010】0010

【表102】[Table 102]

【0011】活性物質における各群の活性化合物の重量
比は、一般に、一般式〔I〕のアミン誘導体またはその
塩の活性物質群の活性化合物1重量部当り、トリフルミ
ゾールを例えば1〜20重量部使用できる。
The weight ratio of the active compounds of each group in the active substance is generally 1 to 20 parts by weight of triflumizole per part by weight of the active compound of the active substance group of the amine derivative of general formula [I] or its salt. Part can be used.

【0012】本発明による活性化合物組合せは、優れた
殺虫および殺菌効果を示し、茎葉散布、トップドレッシ
ング、水中施用、水面施用、土壌表面施用、土壌混和処
理、植穴処理苗浸漬、種子消毒、育苗箱施用燻煙、燻蒸
等により使用することができる。本発明による活性化合
物組合せは、それぞれの活性化合物が単独で施用される
場合より強い殺虫効果および殺菌効果を示すため、作物
に対する薬害がなく、温血動物に対する毒性も低く、安
全に使用できる。本発明の殺虫殺菌組成物は、一般式〔
I〕で表わされる化合物及びトリフルミゾールを有効成
分として含有するものであり、有効成分化合物の純品の
ままでも使用できるが、通常、一般の農薬のとり得る形
態、即ち、水和剤、水溶剤、粉剤、乳剤、粒剤、フロア
ブル、燻煙剤、燻蒸剤等の形態に同時に混合製剤して使
用しても良いし、或いは別々に製剤したものを混合して
使用しても良い。添加剤及び担体としては、固型剤を目
的とする場合は、大豆粉、小麦粉等の植物性粉末、珪藻
土、燐灰石、石膏、タルク、ベントナイト、クレイ等の
鉱物性微粉末、安息香酸ソーダ、尿素、芒硝等の有機お
よび無機化合物が使用される。液体の剤型を目的とする
場合は、植物油、鉱物油、ケロシン、キシレンおよびソ
ルベントナフサ等の石油留分、シクロヘキサン、シクロ
ヘキサノン、ジメチルホルムアミド、ジメチルスルホキ
シド、トリクロルエチレン、メチルイソブチルケトン、
水等を溶剤として使用する。これらの製剤において、均
一なかつ安定な形態をとるために必要ならば界面活性剤
を添加することもできる。このようにして得られた水和
剤、乳剤、水溶液、フロアブル剤は水で所定の濃度に希
釈して懸濁液あるいは乳濁液として、粉剤、粒剤はその
まま、植物に散布する方法で使用される。
The active compound combination according to the invention exhibits an excellent insecticidal and fungicidal effect and can be used in foliage spraying, top dressing, underwater application, water surface application, soil surface application, soil mixing treatment, planting hole treatment, seedling soaking, seed disinfection, seedling raising. It can be used by box application smoke, fumigation, etc. The active compound combination according to the present invention exhibits a stronger insecticidal and fungicidal effect than when each active compound is applied alone, so it can be used safely without causing chemical damage to crops and with low toxicity to warm-blooded animals. The insecticidal and fungicidal composition of the present invention has the general formula [
It contains the compound represented by [I] and triflumizole as active ingredients, and although it can be used as a pure active ingredient compound, it is usually used in the form that general agricultural chemicals can take, i.e., hydrating powders, hydrating powders, etc. They may be used in the form of solvents, powders, emulsions, granules, flowables, fumigants, fumigants, etc., or may be prepared separately and mixed together. As additives and carriers, for solidifying agents, vegetable powders such as soybean flour and wheat flour, fine mineral powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, and clay, sodium benzoate, and urea are used. Organic and inorganic compounds such as mirabilite and the like are used. For liquid formulations, vegetable oil, mineral oil, kerosene, petroleum distillates such as xylene and solvent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, trichloroethylene, methyl isobutyl ketone,
Use water etc. as a solvent. In these preparations, a surfactant may be added if necessary in order to obtain a uniform and stable form. The wettable powders, emulsions, aqueous solutions, and flowables obtained in this way can be diluted with water to a predetermined concentration to form a suspension or emulsion, and the powders and granules can be used as they are by spraying them on plants. be done.

【0013】[0013]

【実施例】次に製剤の実施例を示すが、添加する担体、
界面活性剤等はこれらの実施例に限定されるものではな
い。 実施例1  水和剤 式〔I〕の活性化合物               
 5部トリフルミゾール              
    15部高級アルコール硫酸エステル     
     5部珪藻土               
             70部シリカ      
                        5
部以上を混合して微粉に粉砕し、使用に際し水で希釈し
て懸濁液として散布する。
[Example] Next, examples of formulations will be shown.
Surfactants and the like are not limited to these examples. Example 1 Wettable powder active compound of formula [I]
5 parts triflumizole
15 parts Higher alcohol sulfate ester
5 parts diatomaceous earth
70 parts silica
5
1 part or more is mixed together and ground into a fine powder, and before use, it is diluted with water and sprayed as a suspension.

【参考例】次に製剤の参考例を示すが、添加する担体、
界面活性剤等はこれらの参考例に限定されるものではな
い。 参考例1  水和剤 式〔I〕の活性化合物               
 20部高級アルコール硫酸エステル        
    5部珪藻土                
              70部シリカ     
                         
  5部以上を混合して微粉に粉砕し、使用に際し水で
希釈して懸濁液として散布する。 参考例2  乳剤 式〔I〕の活性化合物               
 15部アルキルフェニルポリオキシエチレン    
5部ジメチルホルムアミド             
   50部キシレン               
             30部以上を混合溶解し、
使用に際し水で希釈して乳濁液として散布する。
[Reference example] Next, a reference example of the formulation is shown.
Surfactants and the like are not limited to these reference examples. Reference Example 1 Wettable powder active compound of formula [I]
20 parts Higher alcohol sulfate ester
5 parts diatomaceous earth
70 parts silica

Mix 5 or more parts, grind into a fine powder, dilute with water and spray as a suspension before use. Reference Example 2 Active compound of emulsion formula [I]
15 parts alkylphenyl polyoxyethylene
5 parts dimethylformamide
50 parts xylene
Mix and dissolve 30 parts or more,
Before use, dilute with water and spray as an emulsion.

【0014】[0014]

【発明の効果】【Effect of the invention】

試験例1  ヒメトビウンカに対する試験発芽後7日を
経過したイネ幼苗を、前記薬剤の実施例1に示された水
和剤、参考例1又は2の処方に従い、所定濃度になるよ
うに水で希釈した組成物の薬液に30秒間浸漬した。風
乾後、処理苗を試験管に入れ、ヒメトビウンカ3令幼虫
10頭を接種した。ガーゼで蓋をして、温度25℃、湿
度65%の恒温室内に置き、7日後に殺虫率を調べた結
果を表2に示した。
Test Example 1 Test against the brown planthopper Rice seedlings 7 days after germination were diluted with water to a predetermined concentration according to the hydrating agent shown in Example 1 of the drug and the formulation of Reference Example 1 or 2. It was immersed in the chemical solution of the composition for 30 seconds. After air-drying, the treated seedlings were placed in a test tube and 10 3rd instar larvae of the Japanese brown planthopper were inoculated. The container was covered with gauze and placed in a constant temperature room at a temperature of 25° C. and a humidity of 65%, and the insecticidal rate was examined after 7 days. The results are shown in Table 2.

【0015】[0015]

【表2】[Table 2]

【0016】試験例2  コムギうどんこ病に対する試
験素焼きポットで栽培したコムギ幼苗(品種「農林61
号」、1.0〜1.2葉期)に本発明組成物の実施例1
に示された水和剤、参考例1又は2の処方に従い所定濃
度になるように水で希釈した薬液を散布し、7日間温室
に保持した後、コムギうどんこ病菌(Erysiphe
  graminis  f.sp.tritici)
の分生胞子を振り払い接種し、22〜25℃の温室で7
日間生育させ、防除効果を調査した。防除効果は、薬剤
処理植物の発病程度を調査し、無処理対照区の発病程度
を基準にして算出し、防除価(%)として表示した。そ
の結果を表3に示した。
Test Example 2 Test against wheat powdery mildew Wheat seedlings (variety "Norin 61") grown in unglazed pots
Example 1 of the composition of the present invention at 1.0-1.2 leaf stage)
A chemical solution diluted with water to a predetermined concentration according to the formulation of the wettable powder shown in Reference Example 1 or 2 was sprayed and kept in a greenhouse for 7 days.
graminis f. sp. tritici)
Shake off the conidia, inoculate, and inoculate in a greenhouse at 22-25℃ for 7 days.
The control effect was investigated after growing for several days. The control effect was calculated by investigating the degree of disease onset in the chemically treated plants, based on the degree of disease onset in the untreated control plot, and expressed as control value (%). The results are shown in Table 3.

【0017】[0017]

【表3】[Table 3]

Claims (1)

【特許請求の範囲】[Claims] 【請求項1】 【化1】 {式中、R1 は無置換2−ピリジル基を除く、置換さ
れていてもよいピリジル基、ピラジル基又はチアゾリル
基を、Xは置換されてもよいアルキレン基もしくはアル
キリデン基を、R2 は水素原子、置換されていてもよ
いアルキル基、アルケニル基、アルキニル基、シクロア
ルキル基、シクロアルケニル基もしくはアリール基、又
はY−R5 を、Yは酸素原子、−CO−を、R5 は
置換されていてもよいアルキル基もしくはアリール基を
、R3 は水素原子、置換されていてもよいアルキル基
、シクロアルキル基を、R4 はシアノ基、又はニトロ
基を示す。}で表わされる化合物又はその塩およびトリ
フルミゾールを含有することを特徴とする農園芸用殺虫
殺菌組成物。
[Claim 1] [Formula 1] {wherein R1 is an optionally substituted pyridyl group, pyrazyl group or thiazolyl group excluding an unsubstituted 2-pyridyl group, and X is an optionally substituted alkylene group or alkylidene group, R2 is a hydrogen atom, an optionally substituted alkyl group, alkenyl group, alkynyl group, cycloalkyl group, cycloalkenyl group or aryl group, or Y-R5, Y is an oxygen atom, -CO- , R5 represents an optionally substituted alkyl group or aryl group, R3 represents a hydrogen atom, an optionally substituted alkyl group or a cycloalkyl group, and R4 represents a cyano group or a nitro group. } or a salt thereof and triflumizole.
JP3159690A 1991-06-04 1991-06-04 Insecticidal composition for agricultural and horticultural use Expired - Fee Related JP2990865B2 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993025080A1 (en) * 1992-06-11 1993-12-23 Nippon Soda Co., Ltd. Termite-proofing agent

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993025080A1 (en) * 1992-06-11 1993-12-23 Nippon Soda Co., Ltd. Termite-proofing agent

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