WO1992021241A1 - Agrohorticultural insecticidal and bactericidal composition - Google Patents
Agrohorticultural insecticidal and bactericidal composition Download PDFInfo
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- WO1992021241A1 WO1992021241A1 PCT/JP1992/000714 JP9200714W WO9221241A1 WO 1992021241 A1 WO1992021241 A1 WO 1992021241A1 JP 9200714 W JP9200714 W JP 9200714W WO 9221241 A1 WO9221241 A1 WO 9221241A1
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- optionally substituted
- insecticidal
- cycloalkyl
- pyridyl
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
Definitions
- the present invention relates to a novel insecticide for agricultural and horticultural use having an excellent insecticidal and fungicidal effect comprising a combination of an amide derivative of the following general formula [I] and an ergosterone cleaving inhibitor (hereinafter referred to as an EBI agent). Regarding the composition.
- the present inventors have studied a more effective use of the amide derivative represented by the following formula I: and studied a combination with an EBI agent. It has been found that chestnuts are effective and fungicidal: ..
- the present invention has the general formula (I): R ;
- R represents an unsubstituted pyridyl group, a pyrazyl group or a thiazolyl group, excluding an unsubstituted 2-pidyl group
- X represents an optionally substituted alkylene group or an alkylidene group
- R represents an aryl group, R represents a hydrogen atom, an optionally substituted alkyl group or a cycloalkyl group, and R represents an optionally substituted alkyl group;
- a toco group a fungicidal composition for agricultural and horticultural use containing the compound represented by or a salt thereof and EBI; j;
- insecticidal / bactericidal composition for example, important insect pests of rice plants, leafhoppers, blasts, for example, aphids, two-naga, leaf snails, and udon, which are important pests such as fruit trees and vegetables.
- Scab, scab important disease of wheat The effect on insect pests, aphids and powdery mildew, was greater than that of a single activated platform alone, indicating synergistic insecticidal and E-killing effects.
- Tri-noremazole which inhibits the second cytochrome P—450
- a halogen atom such as a chloro atom
- a pyridyl group substituted with a cyano group or a lower alkyl group or a halogen atom such as a chloro atom.
- X is a methylene group
- R 2 is a hydrogen atom, a lower alkyl group, an alkyl group substituted with a cyano group, an aryl group, a propargyl group, a cyclopropyl group, a lower alkoxy group, a methoxymethyl group, a tylthiomethyl group, or a chloro atom.
- Optionally substituted benzene a pyridylmethyl group substituted with a kappa atom, a pyridylethyl group substituted with a kappa atom, an acetyl group, or a benzoyl group substituted with a chloro atom.
- R 3 are a hydrogen atom, a low-alkyl group or a cyclobucopyr group which may be substituted with a halogen atom such as a hydrogen atom or a fluorine atom, an R cyano group or two:
- a halogen atom such as a hydrogen atom or a fluorine atom, an R cyano group or two:
- Examples of amine derivatives of the formula: I, which are used in the active substance combination, include the compounds shown in Table 1 below: Preparation of the following amine derivatives or salts thereof Et insecticidal Qi is; use as i is described in WO 9 1 ZG 4 9 6 5 -
- the EBI agents used in the present invention include: Amimehon, 'I, G :) Ajimehon, Bikorunoru, Funina'mo :, Holin, Pyriphenox, Block Koraz, Bewara No. 21 ', Hexaconazol, Mikrov'
- the weight ratio of the active compounds of each group in the active substance is the same as that of the active substance group of the amide derivative of the general formula: 1: or a salt thereof; I! . ⁇ ; ⁇ M quantity part can be used
- the active pesticidal composition according to the present invention exhibits excellent insecticidal and killing effects, foliage application, top dressing, underwater application, surface application ffi, soil surface application, soil admixture, planting hole ⁇ Seedling disinfection, seed disinfection, nursery box application, smoking, fumigation, etc.
- the activated platform assembly according to the present invention is characterized in that each 'tongue' activated platform has a stronger insecticidal and fungicidal effect than the stand applied in Germany, and has no harm to crops.
- the insecticidal fungicidal composition of the present invention has a base represented by the general formula: 1 or a salt thereof and an EBI agent as active ingredients, and can be used as a pure active ingredient compound.
- Ordinary pesticides can take any form, that is, wettable powders, water solvents, water, emulsions, pills, flowables, smokers, fumigants, etc. Separately o You may use a mixture of the following:
- U agent is huge, soybean flour, soybean flour, etc.
- Gypsum Gypsum, talc,-,--, mineral and fine powders, organic and inorganic minerals such as sodium benzoate, urea and sodium sulfate are used ::
- O Bodies that make the dosage form enormous include plants, ⁇ 3 ⁇ 4, kekosin, xylene and petroleum fractions such as' bonnen naphtha ', chikko' ⁇ xane, cyclohexanone, and dimethicone. ./ Reformami, Jimel's Fox, Trichosole, 'Reno,'
- the above mixture is mixed and pulverized into fine powder, and diluted with water before use as a suspension.
- Test example 1 Test for radish binker
- a rice seedling 7 days after germination was transformed into a chemical solution of a composition diluted with water to a predetermined concentration according to the wettable powder shown in Example 1 of the above-mentioned drug and the formulation of Reference Example 1 or 2. It was immersed for 30 seconds. After air-drying, the treated seedlings were placed in a test tube, and 10 to 14 larvae of the third instar larvae of P. persica were inoculated. Cover with gauze, at a temperature of 25, S ⁇ ⁇ 5 5 5 5 Q Q 5 5 5 6 5
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- General Health & Medical Sciences (AREA)
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Abstract
An agrohorticulatural insecticidal and bactericidal composition comprising a compound represented by general formula (I) or its salt and an ergosterol biosynthesis inhibitor, wherein R1 represents optionally substituted pyridyl, pyrazyl or thiazolyl, except for unsubstituted 2-pyridyl; X represents optionally substituted alkylene or alkylidene; R2 represents hydrogen, or optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl, or Y-R5; Y represents oxygen or -CO-; R5 represents optionally substituted alkyl or aryl; R3 represents hydrogen, or optionally substituted alkyl or cycloalkyl; and R4 represents cyano or nitro. This composition has insecticidal and bactericidal effects larger than the effect of a compound having only an insecticidal activity and that of a compound having only a bactericidal activity, respectively, thus being synergistic.
Description
明 細 書 Specification
農園芸用殺虫殺菌組成物 Insecticidal composition for agricultural and horticultural use
技術分野 Technical field
本発明は後記一般式 〔 I 〕 のァ ミ ン誘導体とエルゴステ c 一ル生台成阻害剤 （以下、 E B I剤という） 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。 The present invention relates to a novel insecticide for agricultural and horticultural use having an excellent insecticidal and fungicidal effect comprising a combination of an amide derivative of the following general formula [I] and an ergosterone cleaving inhibitor (hereinafter referred to as an EBI agent). Regarding the composition.
背景技術 Background art
農園芸作物の栽培に当り、 作物の病虫害に対して多数 除薬剤が使用されているが、 その防除効力が不十分であつ 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つたりすることから、 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： 従つ 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。 In the cultivation of agricultural and horticultural crops, many pesticides are used against pests and diseases of crops, but their control efficacy is insufficient, and their use is limited by the emergence of drug-resistant pests and pathogenic bacteria. In addition, many of them are not necessarily satisfactory control agents because they cause phytotoxicity and contamination of plants, or are highly toxic to livestock and fisheries. There is a strong demand for the development of a drug that can be used safely with less.
本発明者らは、 後記一 ¾式 I ： で表わされるァ ミ ン誘導 体のより有効な利用を検討する中て'、 E B I剤との組台せを 研究した結吴、 共力的な殺虫効果および殺菌効栗が得られる ことを見出した： .. The present inventors have studied a more effective use of the amide derivative represented by the following formula I: and studied a combination with an EBI agent. It has been found that chestnuts are effective and fungicidal: ..
発明の開示 Disclosure of the invention
本発明は、 一般式 〔 I 〕
R ; The present invention has the general formula (I): R ;
X X
R X 、 R X,
χ- 、、 R χ-,, R
R :- R:-
(式中、 R : は無置換 2 —ピ 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、 R； 水素原子、 置換されていてもよいアルキル基、 ア ニル基、 アルキニ. 基、 シ クロア キル基、 シク コア^—二 ル基もし '、 ァ —ル基、 又は Y—！^ を、 Yは酸素原子、 一 C O —を、 R - は置換されていてもよいアルキル基もし ； はァリール基を、 R は水素原子、 置換されていてもよいァ キル基、 シク アルキル基を、 はシァノ基 二 トコ 基を示す： で表わされる化合物又はその塩および E B I斉; j を含有する農園芸用殺虫殺菌組成物であり、 新規な活性 ¾|質(Wherein, R represents an unsubstituted pyridyl group, a pyrazyl group or a thiazolyl group, excluding an unsubstituted 2-pidyl group; X represents an optionally substituted alkylene group or an alkylidene group; A hydrogen atom, an optionally substituted alkyl group, an anil group, an alkynyl group, a cycloalkyl group, a cycloalkyl group, a aryl group, or a Y-! ^; R represents an aryl group, R represents a hydrogen atom, an optionally substituted alkyl group or a cycloalkyl group, and R represents an optionally substituted alkyl group; A toco group: a fungicidal composition for agricultural and horticultural use containing the compound represented by or a salt thereof and EBI; j;
O組台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： It has been found that the O braiding shows excellent insecticidal and bactericidal effects:
前記一般式 ： I： oァ ミ ン 導体又はそ o塩に E B I を 配台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¾の効果より大であり、 優れ た共力作 ^を示した。 The general formula: I: The insecticidal effect and the bactericidal effect of the insecticidal and bactericidal composition according to the present invention in which EBI is mounted on an o-ammine conductor or a salt thereof are each greater than the effect of a single active compound, and are excellent. Synergistic ^.
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ゥ ン力、 ョコバイ類、 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、 二 ナガ、 ハマキムシ、 うどんこ病、 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 化台物のみの場'台より効果.が大で、 共力的な殺虫および殺 E 効果を示した。 That is, by applying the insecticidal / bactericidal composition according to the present invention, for example, important insect pests of rice plants, leafhoppers, blasts, for example, aphids, two-naga, leaf snails, and udon, which are important pests such as fruit trees and vegetables. Scab, scab, important disease of wheat The effect on insect pests, aphids and powdery mildew, was greater than that of a single activated platform alone, indicating synergistic insecticidal and E-killing effects.
昆虫細胞内のミ ク口ゾ一厶分画に存在する酵素チ トクロー 厶 P— 4 5 0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、 2 3 0、 1 9 8 6年） 。 It is known that the enzyme cytochrome P-450 present in the microsomal fraction in insect cells oxidatively detoxifies drugs that enter the body. (Ikesho et al., Insect Physiology, Biochemistry, Asakura Shoten, 230, 1986).
二のチ トクロ一厶 P— 4 5 0を阻害する ト リ フノレミ ゾ一ル Tri-noremazole which inhibits the second cytochrome P—450
R, R,
等の E B I斉 ι 〔λΙ· T a t o nら、 P e s t i c i d e B i o c h e m i s t r y a n d P h y s i o l o g y 3 0. 1 7 8 - 1 8 9 1 9 8 8. 中山ら、 日本農薬学会誌 1 ( 1 ) 、 2 3— 3 7、 1 9 8 9 ) ] が一般式 〔 I： のァ 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。 ， 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〕 のァ ミ ン誘導体は下記のごと く定義される： Et al., ΛΙ Taton et al., Pesticide Biochemistry and Physiology 30. 17 8-18 9 9 9 8 8. Nakayama et al., Journal of the Japanese Society of Pesticides 1 (1), 23-37 , 1989)] is considered to exert a synergistic effect by acting on the metabolism of the amide derivative of the general formula [I: in the insect body. The preferred amide derivatives of the general formula [I] used in the active substance combinations according to the invention are defined as follows:
R X 、 R X,
R R
R 式中、 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、 シァノ基又は低級ハ口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 れたビラジル基、 又はクロル原子等のハロゲン原子及び チ ル某より選ばれる 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、 R 2 は水素原子、 低級アルキル基、 シァ ノ基で置換されたアルキル基、 ァリル基、 プロパルギル基、 シクロブロピル基、 低級アルコキシ基、 メ トキシメ ル基、 チルチオメチル基、 クロル原子で置換されてもよいべンジ ,;レ基、 ク口ル原子で置換されたピリ ジルメチル基、 ク口ル原 子で置換されたピリ ジルェチル基、 ァセチル基又はクロル原 子で置換されたベンゾィル基を、 R 3 は水素原子、 ク σル原 子めフ ッ素原子等ハロゲン原子で置換されていても良い低扱 ァルキル基又はシクロブコピル基、 R シァノ基又は二 ：、 σ ：表わ - 本発明による活性物質組合せにお 、て使 Εされる一 ¾式 ； I ： のアミ ン誘導体の例として次の表 1 に示す化合物が挙 げられる： 下記ァミ ン誘導体又はその塩の製造方 ί去及びそれ らの殺虫斉; iとしての使用は、 W O 9 1 Z G 4 9 6 5に記載さ れている-
In the formula, except for an unsubstituted 2-pyridyl group, is substituted with a halogen atom such as a chloro atom, a pyridyl group substituted with a cyano group or a lower alkyl group, or a halogen atom such as a chloro atom. Or a thiazolyl group substituted with one or two selected from a halogen atom such as a chloro atom, X is a methylene group, and R 2 is a hydrogen atom, a lower alkyl group, an alkyl group substituted with a cyano group, an aryl group, a propargyl group, a cyclopropyl group, a lower alkoxy group, a methoxymethyl group, a tylthiomethyl group, or a chloro atom. Optionally substituted benzene; a pyridylmethyl group substituted with a kappa atom, a pyridylethyl group substituted with a kappa atom, an acetyl group, or a benzoyl group substituted with a chloro atom. And R 3 are a hydrogen atom, a low-alkyl group or a cyclobucopyr group which may be substituted with a halogen atom such as a hydrogen atom or a fluorine atom, an R cyano group or two: Examples of amine derivatives of the formula: I, which are used in the active substance combination, include the compounds shown in Table 1 below: Preparation of the following amine derivatives or salts thereof Et insecticidal Qi is; use as i is described in WO 9 1 ZG 4 9 6 5 -
表 1 table 1
12 - / 〃 . CH20CH; リ / 12-/ 〃. CH 2 0CH ;
" ■ " ClIzSCH-, " · " 1^ "■" ClIzSCH-, "·" 1 ^
〃 〃
14 〃 1 CH2 Ο,' ； " " 14 〃 1 CH 2 Ο, ';""
15 CH2 〇广 C1 ！ " \ " 15 CH 2 〇 广 C1! "\"
I I
16 CH2ベ、〇N C1 " "
16 CH 2 〇, N C1 ""
本発明において使用される E B I 剤と して ：、 んミ 、 ' 一 、 ト ：） アジメ ホン、 ビ子ル夕 ノ ール、 フニナ ' モ ：、 ホ リ ン 、 ピリ フ エノ ッ クス、 ブロ ク コラズ、 ベワラ ノ二一 '、 へキサコナゾ一ル、 ミ ク ロフ '夕二ノ プロ ピコナゾ一ル、 シ ニコナゾール、 フヱ ンプロ ピモルフ、 ブロムニナゾ一 /レ等 挙げられる力 、 これらに限定されるものではな ' The EBI agents used in the present invention include: Amimehon, 'I, G :) Ajimehon, Bikorunoru, Funina'mo :, Holin, Pyriphenox, Block Koraz, Bewara No. 21 ', Hexaconazol, Mikrov'
活性物質における各群の活性化合物の重量比は 一 ¾に、 一般式 ： 1 : のァミ ン誘導体またはその塩の活性物質群の;' § 性化台 ¾ 1 重量部当り、 E B I 剤を例えば I！ . 〜 ； π M 量部使用できる The weight ratio of the active compounds of each group in the active substance is the same as that of the active substance group of the amide derivative of the general formula: 1: or a salt thereof; I! . ~; Π M quantity part can be used
本発明による活性 ίヒ合物組台せは、 優れた殺虫および殺匿 効果を示し、 茎葉散布、 ト ッブ ドレッ シング、 水中施用、 面施 ffi、 土壌表面施用、 土壌混和処理、 植穴^理、 苗浸漬、 種子消毒、 育苗箱施用、 燻煙、 燻蒸等により使 S ること さ The active pesticidal composition according to the present invention exhibits excellent insecticidal and killing effects, foliage application, top dressing, underwater application, surface application ffi, soil surface application, soil admixture, planting hole ^ Seedling disinfection, seed disinfection, nursery box application, smoking, fumigation, etc.
本発明による活性化台物組台せは、 それぞれの '；舌 '生化台 Γ 虽独で施用される場台より強く殺虫効果お ひ 菌効旲 示すた 、 作物に対する薬害がな '、 、 温血動^に- る毒1 Ξ も低く 、 安全に使用できる： The activated platform assembly according to the present invention is characterized in that each 'tongue' activated platform has a stronger insecticidal and fungicidal effect than the stand applied in Germany, and has no harm to crops. Low blood venom 1毒, safe to use:
本発明の殺虫殺菌組成 、 一般式 ： 1 : て表わされる 台 ^又はその塩及び E B I 剤を有効成分と してき有するも であり、 有効成分化合物の純品のままでも使^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、 ¾、 乳剤、 拉剤、 フロアブル、 燻煙剤、 燻蒸剤等 0 態に 時に混台製剤して使用しても良いし、 或いは別々に ¾剤し
o ものを混台して使用しても良い： 添 ¾剤及び担体と しては、The insecticidal fungicidal composition of the present invention has a base represented by the general formula: 1 or a salt thereof and an EBI agent as active ingredients, and can be used as a pure active ingredient compound. Ordinary pesticides can take any form, that is, wettable powders, water solvents, water, emulsions, pills, flowables, smokers, fumigants, etc. Separately o You may use a mixture of the following:
U 剤を巨的と'する場台 、 大豆粉、 '、麦粉等の植¾ 末U agent is huge, soybean flour, soybean flour, etc.
！:、 璘 5 .：、 石膏、 タルク、 - 、 ノ - ^ の鉱物性微粉末、 安息香酸ソーダ、 尿素、 芒硝等の有機およ 無機化台物が使 ¾される：： ! :, 璘 5.:, Gypsum, talc,-,--, mineral and fine powders, organic and inorganic minerals such as sodium benzoate, urea and sodium sulfate are used ::
¾体 o剤型を巨的とする場台は、 植物 、 绽¾ 、 ケコ シ ン、 キシレ ンおよひ'ソルヘン トナフサ等の石油留分、 シク コ '\キサン 、 シクロへキサノ ン、 ジメ チ ./レホル厶ア ミ 、 ジメ ル ス ホキシ ト 、 ト リ コゾレエ 、 'レ ノ ， ' フ O Bodies that make the dosage form enormous include plants, 绽 ¾, kekosin, xylene and petroleum fractions such as' solchen naphtha ', chikko' \ xane, cyclohexanone, and dimethicone. ./ Reformami, Jimel's Fox, Trichosole, 'Reno,'
^ ト ン 、 水等を溶剤と して使^する： これら 製 において. 一なかつ安定な形態をとるために必要なら（ 界面活性剤を ^ Πするこ もできる。 このようにして得られた水和斉 i]、 ?i 剤、 水溶液、 フロアブル ¾は水で所定の濃度に希釈して懸灑 液あるいは乳濁液として、 粉剤、 ^剤はそのまま、 植物に散 布する方法で使用される U 発明を実施するための最良の ¾態 ^ Use tonnes, water, etc. as solvents: In these products. If necessary to obtain a uniform and stable form (a surfactant can be used. The water thus obtained can be used). Kazui i],? I agent, aqueous solution, flowable ¾ is diluted to a predetermined concentration with water and used as a suspension or emulsion. BEST MODE FOR CARRYING OUT THE INVENTION
； に製剤の実施 を示す 、 添力:]する担 、 界面活性剤等 二れら ο実施^に 艮定されるものではない： 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤 製 剤.
実旌^ 1 水和^ Jeongjeong ^ 1 Hydration ^
一般式 ： 1 : で表わされる化台物また その塩 5 ^ General formula: 1: Chemical compound represented by: or its salt 5 ^
E B I剤 i 5 E B I agent i 5
高 ¾アルコール硫酸エステル 5 ^ High alcohol sulfate 5 ^
珪藻土 Diatomaceous earth
J ρμ 上を混台して微粉に粉碎し、 使用に際し水で希釈して懸
濁液と して散布する。 Mix on Jρμ and pulverize into fine powder, dilute with water before use and suspend Spray as a suspension.
^ 1.¾ ^ 1.¾
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 c Then shows a reference example of preparation, the carrier to be added, not surface active agents and the like to be limited to these reference examples c
参考例 1 水和剤 Reference Example 1 wettable powder
一般式 〔 I ： で表わされる化合物またはその塩 A compound represented by the general formula [I: or a salt thereof
高級アルコール硫酸エステル 5 ¾ 珪藻土 Higher alcohol sulfate 5 ¾ diatomaceous earth
シ リ 77 Series 77
以上を混台して微粉に粉砕し、 使用に際し水で希^ Lて 濁液と して散布する。 The above mixture is mixed and pulverized into fine powder, and diluted with water before use as a suspension.
参考例 2 乳剤 Reference Example 2 Emulsion
一般式 〔 I 〕 で表わされる化合物またはその塩 1 5 Si. アルキルフ ヱニルポリオキシエチレ ン 5部 ジメ チルホルムア ミ ド 5 0部 Compound represented by the general formula [I] or a salt thereof 15 Si. Alkylphenylpolyoxyethylene 5 parts Dimethylformamide 50 parts
ο キシ レン 3 0部咅 以上を混台溶解し、 使用に際し水で希釈して乳濁液と して 散布する。 ο Dissolve 30 parts or more of xylene in a mixing stand, dilute with water before use, and spray as an emulsion.
産業上の利用可能性 Industrial applicability
試験例 1 ヒメ ト ビゥ ンカに対する試験 Test example 1 Test for radish binker
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の処方に準じ、 所定濃度に なるように水で希釈した組成物の薬液に 3 0秒間浸漬した。 風乾後、 処理苗を試験管に入れ、 ヒメ トビゥ ンカ 3令幼虫 1 0〜 1 4頭を接種した。 ガーゼで蓋をして、 温度 2 5で、
S ベた纟吉吴 度 6 5 Q:の恒温室内に置き、 了 a後に ^^ A rice seedling 7 days after germination was transformed into a chemical solution of a composition diluted with water to a predetermined concentration according to the wettable powder shown in Example 1 of the above-mentioned drug and the formulation of Reference Example 1 or 2. It was immersed for 30 seconds. After air-drying, the treated seedlings were placed in a test tube, and 10 to 14 larvae of the third instar larvae of P. persica were inoculated. Cover with gauze, at a temperature of 25, S 纟 纟 5 5 5 Q Q 5 5 5 6 5
ZZ ~ ，：！ ZZ ~,:!
；'仝 s¾ J 下 c 表において 台物番号 表 1 中の
; '仝S¾ J platform compound numbers on Table 1 under c Table
I 丰 I 丰
！ 衣 o 6 ! Clothing o 6
1 F 1 F
(ppm) 喻 : ィ匕 番号 2 ÷ (Α) ； 8卞 125 ' 100 (ppm) 喻: No. 2 number (÷); 8 Bye 125 '100
2+(B) 8 +500 100 2+ (B) 8 +500 100
\ 17 + (Λ) ■ 8 ÷125 100 ： i 17+(B) , 8+500 100\ 17 + (Λ) ■ 8 ÷ 125 100: i 17+ (B), 8 + 500 100
1 20丄（A) 8 -125 100 1 20 丄 (A) 8 -125 100
20+(B) i 8 +500 . ！ 100 ί 20+ (B) i 8 +500. 100 ί
1 27 -(A) 8 125 ' 100 ！ 1 27-(A) 8 125 '100!
1 2T-(BJ 8 500 100 1 2T- (BJ 8 500 100
28 (A) 8一 125 100 28 (A) 8 1 125 100
28-(B δ -500 10028- (B δ -500 100
30 - (A) 8-^125 10030-(A) 8- ^ 125 100
30-r(B) 8 +500 100 ,30-r (B) 8 +500 100,
2 8 402 8 40
17 i 8 i 30 ；17 i 8 i 30;
20 1 8 ' 5020 1 8 '50
27 ' 8 2027 '8 20
28 8 3028 8 30
30 8 3030 8 30
(A; 125 G(A; 125 G
(BJ 500 1(BJ 500 1
(注） ：トリフルミゾ-ル (Note): Triflumisol
：フエナリモル
： Fenarimol
試験^ 2 ニムギぅどんこ病に対する試験 Trial ^ 2 Trials for barley powdery mildew
素焼き ッ ト 栽培したコ厶ギ E —農^ ： 号— Unglazed cultivated wheat E —Agriculture ^: No.—
1 . 0〜 し 2葉期） に本発明組成物の実施 .； 1 二示され 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 ギうどんこ病囷 （ E r y—S i p h e g r a m i n i s f . s p . t r i t i c i ) の分生胞子を振り払い接種し、 2 2〜 2 5ての温室で了 日間生育させ、 防除効果を調査した: ^除 杲 、 薬剤 理植物の発病程度を調査し、 ^ 理 ^ S O ¾病程度を基準にして算 し、 除 ' こ して表示 した： その結果を表 3 に示した：
1.0 to 2 leaf stage); 1) a wettable powder, and a drug solution diluted with water to a predetermined concentration according to the formulation of Reference Example 1 or 2 was sprayed; After holding in a greenhouse for a day, the conidiospores of wheat powdery mildew (Ery-Siphegraminisf.sp.tritici) were shaken off and inoculated, and allowed to grow in a greenhouse for 22 to 25 days to complete control. The extent of disease development in pharmacological plants was investigated, calculated based on the degree of disease, and ex- tracted and displayed. The results are shown in Table 3:
21 125 021 125 0
O了 31.5 0 O end 31.5 0
125 ： 0 125: 0
25 31.5 025 31.5 0
27 125 υ27 125 υ
2丁 31.5 02 31.5 0
(A) 12.5 i 90(A) 12.5 i 90
(c; 12.5 95(c; 12.5 95
： A): ' ミ'レ'; : A): 'Mi're';
'； C): ί·リアジ ン 4
'; C): リ ア · Riagin 4
Claims
(1) (1)
R R
II
N N
R 一 X R one X
式 - • ' R Expression-• 'R
R R
I I
ί式中、 R , 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、 ビラジル基又はチアソ 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、 ァルケ ニル基、 アルキニル基、 シクロアルキル基、 シクロアルケ二 ル基もしく はァリール基、 又は Y— R5 を、 Yは酸素原子、 — C〇—を、 R5 は置換されていてもよいアルキル基もしく はァリール基を、 R3 は水素原子、 置換されていてもよいァ ルキル基、 シクロアルキル基を、 R4 はシァノ基、 又はニ ト 口基を示す。 } で表わされる化合物又はその塩およびエルゴ ステロール生合成阻害剤を含有することを特徵とする農園芸 用殺虫殺菌組成物。
In the formula, R represents an unsubstituted pyridyl group, a virazyl group or a thiazolyl group, excluding an unsubstituted 2-pyridyl group, and X represents an optionally substituted alkylene group or an alkylidene group. R 2 represents a hydrogen atom, an optionally substituted alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group or an aryl group, or Y—R 5 , Y represents an oxygen atom, —C the 〇-, the R 5 alkyl group which may optionally be substituted or may Ariru group, R 3 is a hydrogen atom, an optionally substituted § alkyl group, a cycloalkyl group, R 4 is Shiano group, or Indicates a nitro group. } A pesticidal fungicidal composition for agricultural and horticultural use, comprising a compound represented by the formula: or a salt thereof, and an ergosterol biosynthesis inhibitor.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3/159690 | 1991-06-04 | ||
| JP3159690A JP2990865B2 (en) | 1991-06-04 | 1991-06-04 | Insecticidal composition for agricultural and horticultural use |
| JP16742691A JPH04368304A (en) | 1991-06-13 | 1991-06-13 | Insecticidal and fungicidal composition for agriculture and horticulture |
| JP3/167426 | 1991-06-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1992021241A1 true WO1992021241A1 (en) | 1992-12-10 |
Family
ID=26486407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP1992/000714 WO1992021241A1 (en) | 1991-06-04 | 1992-06-02 | Agrohorticultural insecticidal and bactericidal composition |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO1992021241A1 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996003045A1 (en) * | 1994-07-28 | 1996-02-08 | Bayer Aktiengesellschaft | Pesticide |
| US5977148A (en) * | 1995-04-11 | 1999-11-02 | Nipppon Soda Co., Ltd. | Termiticide |
| US6436968B1 (en) | 1998-06-17 | 2002-08-20 | Bayer Aktiengesellschaft | Agents for controlling plant pests |
| US6436976B1 (en) | 1998-06-10 | 2002-08-20 | Bayer Aktiengesellschaft | Agents for combating plant pests |
| EP2298077A1 (en) | 1998-06-10 | 2011-03-23 | Bayer CropScience AG | Agents for combatting plant pests |
| RU2431960C9 (en) * | 1994-07-28 | 2013-05-20 | Байер Акциенгезелльшафт | Synergetic insecticide |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04154741A (en) * | 1989-10-06 | 1992-05-27 | Nippon Soda Co Ltd | Amine derivative, its production and insecticide |
-
1992
- 1992-06-02 WO PCT/JP1992/000714 patent/WO1992021241A1/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04154741A (en) * | 1989-10-06 | 1992-05-27 | Nippon Soda Co Ltd | Amine derivative, its production and insecticide |
Cited By (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7008903B2 (en) | 1994-07-28 | 2006-03-07 | Bayer Aktiengesellschaft | Pesticide |
| US6114362A (en) * | 1994-07-28 | 2000-09-05 | Bayer Aktiengesellschaft | Compositions for the control of plant pests |
| US6297263B1 (en) | 1994-07-28 | 2001-10-02 | Bayer Aktiengesellschaft | Pesticide |
| RU2431960C9 (en) * | 1994-07-28 | 2013-05-20 | Байер Акциенгезелльшафт | Synergetic insecticide |
| US7884049B2 (en) | 1994-07-28 | 2011-02-08 | Bayer Cropscience Ag | Compositions for the control of plant pests |
| KR100386956B1 (en) * | 1994-07-28 | 2003-08-25 | 바이엘 악티엔게젤샤프트 | Pest Control Composition |
| WO1996003045A1 (en) * | 1994-07-28 | 1996-02-08 | Bayer Aktiengesellschaft | Pesticide |
| EP1609361A3 (en) * | 1994-07-28 | 2010-01-06 | Bayer CropScience Aktiengesellschaft | Compositions for controlling plant pests |
| US5977148A (en) * | 1995-04-11 | 1999-11-02 | Nipppon Soda Co., Ltd. | Termiticide |
| US7696237B2 (en) | 1998-06-10 | 2010-04-13 | Bayer Cropscience Ag | Agents for combating plant pests |
| EP2305035A1 (en) | 1998-06-10 | 2011-04-06 | Bayer CropScience AG | Agents for combatting plant pests |
| US7232840B2 (en) | 1998-06-10 | 2007-06-19 | Bayer Cropscience Ag | Agents for combating plant pests |
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| US7763266B2 (en) | 1998-06-10 | 2010-07-27 | Bayer Cropscience Ag | Agents for combating plant pests |
| US6436976B1 (en) | 1998-06-10 | 2002-08-20 | Bayer Aktiengesellschaft | Agents for combating plant pests |
| EP2298077A1 (en) | 1998-06-10 | 2011-03-23 | Bayer CropScience AG | Agents for combatting plant pests |
| EP2298076A1 (en) | 1998-06-10 | 2011-03-23 | Bayer CropScience AG | Agents for combatting plant pests |
| EP2301353A1 (en) | 1998-06-10 | 2011-03-30 | Bayer CropScience AG | Agents for combatting plant pests |
| US8617581B2 (en) | 1998-06-10 | 2013-12-31 | Bayer Intellectual Property Gmbh | Agents for combating plant pests |
| EP2305031A1 (en) | 1998-06-10 | 2011-04-06 | Bayer CropScience AG | Agents for combatting plant pests |
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| US8153665B2 (en) | 1998-06-17 | 2012-04-10 | Bayer Aktiengesellschaft | Agents for controlling plant pests |
| US6436968B1 (en) | 1998-06-17 | 2002-08-20 | Bayer Aktiengesellschaft | Agents for controlling plant pests |
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