JPH06135933A - Substituted alkenyl ketone derivative and insecticide - Google Patents
Substituted alkenyl ketone derivative and insecticideInfo
- Publication number
- JPH06135933A JPH06135933A JP22365092A JP22365092A JPH06135933A JP H06135933 A JPH06135933 A JP H06135933A JP 22365092 A JP22365092 A JP 22365092A JP 22365092 A JP22365092 A JP 22365092A JP H06135933 A JPH06135933 A JP H06135933A
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- formula
- haloalkyl
- substituted
- Prior art date
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- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【０００２】[0002]
【産業上の利用分野】本発明は置換アルケニルケトン誘
導体及びこれを有効成分として含有する殺虫剤に関する
ものである。TECHNICAL FIELD The present invention relates to a substituted alkenyl ketone derivative and an insecticide containing the derivative as an active ingredient.
【０００３】[0003]
【従来の技術】これまで、２−アミノ−１−アルケニル
トリハロメチルケトン誘導体として、次の化合物が知
られているがその殺虫活性については知られていない。
例えば一般式2. Description of the Prior Art The following compounds have been known as 2-amino-1-alkenyl trihalomethyl ketone derivatives, but their insecticidal activity has not been known.
For example, the general formula
【０００４】[0004]
【化３】 [Chemical 3]
【０００５】（但し、式中、Ｘは塩素原子又はフッ素原
子を示し、Ｒ7はメチル基又はフェニル基を示し、Ｒ8は
エチル基又はフェニル基を示し、Ｒ9は水素原子又はエ
チル基を示す。）で示される化合物〔シンセシス（Synt
hesis）第１０１３頁（１９８６年）〕、一般式(Wherein X represents a chlorine atom or a fluorine atom, R 7 represents a methyl group or a phenyl group, R 8 represents an ethyl group or a phenyl group, and R 9 represents a hydrogen atom or an ethyl group. Compound) [synthesis (Synt
hesis) p. 1013 (1986)], general formula
【０００６】[0006]
【化４】 [Chemical 4]
【０００７】（式中、Ｒ10は水素原子、エチル基、フェ
ニル基、ベンジル基又は２−ピリジル基等を示す。）で
示される化合物〔Zh. Org. Khim.２６巻、９号、１８７
７頁（１９９０年）〕、式(In the formula, R 10 represents a hydrogen atom, an ethyl group, a phenyl group, a benzyl group, a 2-pyridyl group or the like.) [Zh. Org. Khim. 26, No. 9, 187]
P. 7 (1990)], formula
【０００８】[0008]
【化５】 [Chemical 5]
【０００９】（式中、Ｒ11は２−チアゾリル基、３−ク
ロロ−５−トリフルオロメチル−２−ピリジル基、４−
トリフルオロメチル−２−ピリミジニル基等を示す。）
で示される化合物〔Gaodeng Xuexiao Huaxue Xuebao,６
巻、９号、７９９頁（１９８５年）〕、また、２−
（１,３−ジメチル−５−ピラゾリルアミノ）−１,１,
１,５,５,５−ヘキサフルオロ−２−ペンテン−４−オ
ン〔Pol. J. Chem.５５巻、１０号、１９９５頁（１９
８１年）〕等である。この他、特開平３−１５１３６３
号公報明細書には一般式(In the formula, R 11 is 2-thiazolyl group, 3-chloro-5-trifluoromethyl-2-pyridyl group, 4-
A trifluoromethyl-2-pyrimidinyl group and the like are shown. )
Compound represented by [Gaodeng Xuexiao Huaxue Xuebao, 6
Vol. 9, No. 7, 799 (1985)], and 2-
(1,3-dimethyl-5-pyrazolylamino) -1,1,
1,5,5,5-hexafluoro-2-penten-4-one [Pol. J. Chem. Vol. 55, No. 10, p. 1995 (19
1981)] etc. In addition to this, JP-A-3-151363
No.
【００１０】[0010]
【化６】 [Chemical 6]
【００１１】（式中、Ｒ12は独立してハロゲン原子、ア
ルキル等から選択される１個又はそれ以上の置換基を有
するピリジル基又はチアゾリル基を示し、Ｒ13は水素原
子、アルキル基もしくはアルキルカルボニル基を示し、
Ｒ14はアルキル基を示し、Ｒ15はハロアルキル基を示
し、Ｙは硫黄又は式Ｎ−Ｒ16基を示し、ｎは０又は１で
ある。）を有するブテノン化合物が殺虫活性を有すると
記載されている。(In the formula, R 12 independently represents a pyridyl group or a thiazolyl group having one or more substituents selected from a halogen atom, alkyl, etc., and R 13 represents a hydrogen atom, an alkyl group or an alkyl group. Represents a carbonyl group,
R 14 represents an alkyl group, R 15 represents a haloalkyl group, Y represents sulfur or a group of formula N—R 16 and n is 0 or 1. A butenone compound having a) is described as having insecticidal activity.
【００１２】[0012]
【発明が解決しようとする課題】本発明は殺虫活性がさ
らに改良された新規な置換アルケニルケトン誘導体及び
これを含む殺虫剤を提供するものである。DISCLOSURE OF THE INVENTION The present invention provides a novel substituted alkenyl ketone derivative having further improved insecticidal activity and an insecticide containing the same.
【００１３】[0013]
【課題を解決するための手段】本発明者らは有用な殺虫
剤を開発すべく種々の置換アルケニルケトン誘導体を合
成し、その殺虫活性について検討を重ねた結果、本発明
化合物が種々の有害昆虫類、特にトビイロウンカ、ツマ
グロヨコバイなどの水稲害虫及びコナガなどの園芸害虫
に対し極めて優れた殺虫活性を有することを見い出し本
発明を完成した。The present inventors have synthesized various substituted alkenyl ketone derivatives in order to develop a useful insecticide, and have studied the insecticidal activity thereof. The present invention has been completed by finding that they have extremely excellent insecticidal activity against insects such as rice plant pests, rice leafhoppers and rice leaf pests and horticultural pests such as diamondback moth.
【００１４】すなわち、本発明の置換アルケニルケトン
誘導体は一般式〔Ｉ〕That is, the substituted alkenyl ketone derivative of the present invention has the general formula [I]
【００１５】[0015]
【化７】 [Chemical 7]
【００１６】〔式中、Ｒ1はハロアルキル基を示し、Ｒ2
は水素原子を示し、Ｒ3は分岐してもよいアルキル基又
はフェニル基（当該フェニル基はハロゲン原子、分岐し
てもよいアルキル基、アルコキシ基又はハロアルキル基
で置換されてもよい。）を示し、Ｒ4は水素原子、分岐
してもよいアルキル基及びハロアルキル基を示し、Ｚは
ピリジル基、ピリミジニル基及びチアゾリル基（当該ピ
リジル基、ピリミジニル基及びチアゾリル基はハロゲン
原子、分岐してもよいアルキル基、アルコキシ基又はハ
ロアルキル基で置換されてもよい。）又は式[In the formula, R 1 represents a haloalkyl group, and R 2
Represents a hydrogen atom, and R 3 represents a branched alkyl group or a phenyl group (the phenyl group may be substituted with a halogen atom, a branched alkyl group, an alkoxy group or a haloalkyl group). , R 4 represents a hydrogen atom, an alkyl group which may be branched or a haloalkyl group, and Z is a pyridyl group, a pyrimidinyl group or a thiazolyl group (the pyridyl group, the pyrimidinyl group or the thiazolyl group is a halogen atom or an alkyl group which may be branched). A group, an alkoxy group or a haloalkyl group) or a formula
【００１７】[0017]
【化８】 [Chemical 8]
【００１８】（式中、Ｒ5、Ｒ6は水素原子、分岐しても
よいアルキル基及びハロアルキル基を示し、Ｒ5とＲ6は
炭素数３〜７の環を形成することもできる。Ｑはハロゲ
ン原子、分岐してもよいアルキル基、ハロアルキル基、
アルコキシ基、ハロアルコキシ基及びフェノキシ基より
任意に選ばれる置換基を有していてもよいフェニル基又
は置換基を有していてもよいピリジル基を示す。）で表
される基を示す。〕で表され、殺虫剤はこの化合物を有
効成分として含有するしてなる。(In the formula, R 5 and R 6 represent a hydrogen atom, a branched alkyl group and a haloalkyl group, and R 5 and R 6 can form a ring having 3 to 7 carbon atoms. Is a halogen atom, an alkyl group which may be branched, a haloalkyl group,
A phenyl group optionally having a substituent selected from an alkoxy group, a haloalkoxy group and a phenoxy group or a pyridyl group optionally having a substituent is shown. ) Represents a group represented by. ] And the insecticide contains this compound as an active ingredient.
【００１９】本発明化合物は一般的に以下の合成法によ
り製造できるが、これらに限定されるものではない。The compound of the present invention can be generally prepared by the following synthetic methods, but is not limited thereto.
【００２０】[0020]
【化９】 [Chemical 9]
【００２１】（式中、Ｒ17は低級アルキル基を示し、Ｒ
1、Ｒ2、Ｒ3、Ｒ4、及びＺは前記と同じ意味を示す。）(In the formula, R 17 represents a lower alkyl group,
1 , R 2 , R 3 , R 4 , and Z have the same meanings as described above. )
【００２２】すなわち、一般式〔I〕の化合物は一般式
〔II〕の化合物１当量に対し、一般式〔III〕の化合物
１当量を、適当な溶媒中で反応させることにより得るこ
とができる。ここで反応温度は０℃より溶媒の沸点温度
範囲、好ましくは４０〜８０℃である。また０.５〜２
０時間させる。使用される溶媒としては、例えばメタノ
ール、エタノール等のアルコール類、ジエチルエーテ
ル、テトラヒドロフラン、ジオキサン、ジグライム等の
エーテル類、ペンタン、ヘキサン、石油エーテル等の脂
肪族炭化水素類、ジクロロメタン、ジクロロエタン、ク
ロロホルム、四塩化炭素等のハロゲン化炭化水素類、ア
セトニトリル等のニトリル類、ジメチルホルムアミド、
ジメチルアセトアミド、ジメチルスルホキシド等の非プ
ロトン性極性溶媒類、及びこれらから選択される溶媒を
組み合わせた混合溶媒を用いることができる。That is, the compound of the general formula [I] can be obtained by reacting 1 equivalent of the compound of the general formula [II] with 1 equivalent of the compound of the general formula [III] in a suitable solvent. Here, the reaction temperature is from 0 ° C to the boiling point temperature range of the solvent, preferably from 40 to 80 ° C. Also 0.5-2
Let it run for 0 hours. Examples of the solvent used include alcohols such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran, dioxane, and diglyme, aliphatic hydrocarbons such as pentane, hexane, and petroleum ether, dichloromethane, dichloroethane, chloroform, and four. Halogenated hydrocarbons such as carbon chloride, nitriles such as acetonitrile, dimethylformamide,
Aprotic polar solvents such as dimethylacetamide and dimethyl sulfoxide, and mixed solvents obtained by combining solvents selected from these can be used.
【００２３】[0023]
【実施例】次に、一般式〔Ｉ〕で表される本発明化合物
を表１〜表８に例示する。なお、表中Phはフェニル基を
意味する。EXAMPLES The compounds of the present invention represented by the general formula [I] are shown in Tables 1-8. In the table, Ph means a phenyl group.
【００２４】[0024]
【表１】 [Table 1]
【００２５】[0025]
【表２】 [Table 2]
【００２６】[0026]
【表３】 [Table 3]
【００２７】[0027]
【表４】 [Table 4]
【００２８】[0028]
【表５】 [Table 5]
【００２９】[0029]
【表６】 [Table 6]
【００３０】[0030]
【表７】 [Table 7]
【００３１】[0031]
【表８】 [Table 8]
【００３２】次に実施例を挙げて本発明化合物の製造法
を具体的に説明する。Next, the production method of the compound of the present invention will be specifically described with reference to examples.
【００３３】実施例１ ２−（４,６−ジメチル−２−ピリミジルアミノ）−１
−プロペニルトリフロオロメチルケトン（化合物３）の
合成 ２−メトキシ−５,５,５−トリフロオロ−２−ペンテン
−４−オン（３g）を６０mlのアセトニトリルに溶解さ
せ、これに４,６−ジメチル−２−アミノピリミジン
（２.２g）を加え、１０時間加熱還流した。反応終了
後、反応液を濃縮し濃縮物を酢酸エチル−ｎ−ヘキサン
混合溶液を展開溶媒とするシリカゲル（ワコーゲルＣ−
２００：和光純薬株式会社製造）・クロマトグラフィー
に付し、淡黄色結晶（融点：６９〜７０℃）の目的物
１.８gを得た（収率３８.９％）。Example 1 2- (4,6-Dimethyl-2-pyrimidylamino) -1
-Synthesis of propenyltrifluoromethylketone (Compound 3) 2-Methoxy-5,5,5-trifluoro-2-penten-4-one (3 g) was dissolved in 60 ml of acetonitrile, and 4,6-dimethyl was added thereto. 2-Aminopyrimidine (2.2 g) was added and the mixture was heated under reflux for 10 hours. After completion of the reaction, the reaction solution is concentrated, and the concentrate is silica gel (Wakogel C-
200: manufactured by Wako Pure Chemical Industries, Ltd.) ・ Chromatography gave 1.8 g of the target product as pale yellow crystals (melting point: 69-70 ° C.) (yield 38.9%).
【００３４】 ＮＭＲデータ（６０ＭＨｚ、ＣＤＣｌ3溶媒、δ値） ２.４０ （ｓ,６Ｈ） ２.６３ （ｓ,３Ｈ） ５.５０ （ｓ,１Ｈ） ６.７０ （ｓ,１Ｈ） １２.２７〜１２.６０ （ｂｓ,１Ｈ）NMR data (60 MHz, CDCl 3 solvent, δ value) 2.40 (s, 6H) 2.63 (s, 3H) 5.50 (s, 1H) 6.70 (s, 1H) 12.27 ~ 12.60 (bs, 1H)
【００３５】実施例２ ２−（４−クロロ−α,α−ジメチルベンジルアミノ）
−１−プロペニルペルフルオロプロピルケトン（化合物
２７）の合成 ２−メトキシ−５,５,６,６,７,７,７−ヘプタフロオロ
−２−ペンテン−４−オン（３g）を６０mlのアセトニ
トリルに溶解させ、これに４−クロロ−α,α−ジメチ
ルベンジルアミン（１.９g）を加え、３時間加熱還流し
た。反応終了後、反応液を濃縮し濃縮物を酢酸エチル−
ｎ−ヘキサン混合溶液を展開溶媒とするシリカゲル（ワ
コーゲルＣ−２００）・クロマトグラフィーに付し、黄
色透明液体の目的物１.２g（屈折率１.４９８３）を得
た（収率２６.４％）。Example 2 2- (4-chloro-α, α-dimethylbenzylamino)
Synthesis of -1-propenyl perfluoropropyl ketone (Compound 27) 2-Methoxy-5,5,6,6,7,7,7-heptafluoro-2-penten-4-one (3 g) was dissolved in 60 ml of acetonitrile. 4-chloro-α, α-dimethylbenzylamine (1.9 g) was added thereto, and the mixture was heated under reflux for 3 hours. After completion of the reaction, the reaction solution was concentrated and the concentrate was diluted with ethyl acetate-
Chromatography was performed on silica gel (Wakogel C-200) using an n-hexane mixed solution as a developing solvent to obtain 1.2 g of the target product as a yellow transparent liquid (refractive index 1.4983) (yield 26.4%). ).
【００３６】 ＮＭＲデータ（６０ＭＨｚ、ＣＤＣｌ3溶媒、δ値） １.６７ （ｓ,３Ｈ） １.７３ （ｓ,６Ｈ） ５.３０ （ｓ,１Ｈ） ７.２７ （ｄｄ,４Ｈ） １１.７３〜１２.２３ （ｂｓ,１Ｈ）NMR data (60 MHz, CDCl 3 solvent, δ value) 1.67 (s, 3H) 1.73 (s, 6H) 5.30 (s, 1H) 7.27 (dd, 4H) 11.73 ~ 12.23 (bs, 1H)
【００３７】実施例３ ２−〔Ｎ−（６−クロロ−３−ピリジルメチル）−Ｎ−
メチルアミノ〕−１−プロペニルトリフロオロメチルケ
トン（化合物４５）の合成 ２−メトキシ−５,５,５−トリフロオロ−２−ペンテン
−４−オン（３g）を、６０mlのアセトニトリルに溶解
させこれにＮ−（６−クロロ−３−ピリジルメチル）−
２−メチルアミン（２.８g）を加え、３時間加熱した。
反応終了後、反応液を濃縮し濃縮物を酢酸エチル−ｎ−
ヘキサン混合溶液を展開溶媒とするシリカゲル（ワコー
ゲルＣ−２００）・クロマトグラフィーに付し、黄褐色
透明粘凋液体の目的物３.２g（屈折率１.５７５２）を
収率６１.３％で得た。Example 3 2- [N- (6-chloro-3-pyridylmethyl) -N-
Synthesis of Methylamino] -1-propenyltrifluoromethylketone (Compound 45) 2-Methoxy-5,5,5-trifluoro-2-penten-4-one (3 g) was dissolved in 60 ml of acetonitrile and added thereto. N- (6-chloro-3-pyridylmethyl)-
2-Methylamine (2.8g) was added and heated for 3 hours.
After completion of the reaction, the reaction solution was concentrated and the concentrate was diluted with ethyl acetate-n-
Chromatography was performed on silica gel (Wakogel C-200) using a hexane mixed solution as a developing solvent to obtain 3.2 g of the target product as a yellowish brown transparent viscous liquid (refractive index 1.5752) with a yield of 61.3%. It was
【００３８】 ＮＭＲデータ（６０ＭＨｚ、ＣＤＣｌ3溶媒、δ値） ２.６３ （ｓ,３Ｈ） ３.１０ （ｓ,３Ｈ） ４.６３ （ｓ,２Ｈ） ５.３３ （ｓ,１Ｈ） ７.１７〜７.６７ （ｍ,２Ｈ） ８.２０ （ｄ,１Ｈ）NMR data (60 MHz, CDCl 3 solvent, δ value) 2.63 (s, 3H) 3.10 (s, 3H) 4.63 (s, 2H) 5.33 (s, 1H) 7.17 ~ 7.67 (m, 2H) 8.20 (d, 1H)
【００３９】本発明の殺虫剤は一般式〔Ｉ〕で示される
置換アルケニルケトン誘導体を有効成分としてなる。本
発明化合物を殺虫剤として使用するには本発明化合物そ
れ自体で用いてもよいが、製剤化に一般的に用いられる
担体、界面活性剤、分散剤又は補助剤等を配合して、粉
剤、水和剤、乳剤、微粒剤又は粒剤等に製剤して使用す
ることもできる。製剤化に際して用いられる担体として
はジークライト、タルク、ベントナイト、クレー、カオ
リン、珪藻土、ホワイトカーボン、バーミキュライト、
消石灰、珪砂、硫安、尿素等の固体担体、イソプロピル
アルコール、キシレン、シクロヘキサノン、メチルナフ
タレン等の液体担体等が挙げられる。界面活性剤及び分
散剤としてはアルキルベンゼンスルホン酸金属塩、ジナ
フチルメタンジスルホン酸金属塩、アルコール硫酸エス
テル塩、アルキルアリールスルホン酸塩、リグニンスル
ホン酸塩、ポリオキシエチレングリコールエーテル、ポ
リオキシエチレンアルキルアリールエーテル、ポリオキ
シエチレンソルビタンモノアルキレート等が挙げられ
る。補助剤としてはカルボキシメチルセルロース、ポリ
エチレングリコール、アラビアゴム等があげられる。The insecticide of the present invention comprises a substituted alkenyl ketone derivative represented by the general formula [I] as an active ingredient. In order to use the compound of the present invention as an insecticide, the compound of the present invention may be used by itself, but a carrier generally used for formulation, a surfactant, a dispersant, an auxiliary agent or the like is added, and a powder, It can also be used by formulating it into a wettable powder, an emulsion, a fine granule or a granule. Carriers used for formulation include Sieglite, talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite,
Examples thereof include solid carriers such as slaked lime, silica sand, ammonium sulfate and urea, and liquid carriers such as isopropyl alcohol, xylene, cyclohexanone and methylnaphthalene. Surfactants and dispersants include alkylbenzene sulfonic acid metal salts, dinaphthylmethane disulfonic acid metal salts, alcohol sulfate ester salts, alkylaryl sulfonates, lignin sulfonates, polyoxyethylene glycol ethers, polyoxyethylene alkylaryl ethers. , Polyoxyethylene sorbitan monoalkylate and the like. Examples of the auxiliary agent include carboxymethyl cellulose, polyethylene glycol, gum arabic and the like.
【００４０】有効成分の配合割合については必要に応じ
て適宜選ばれるが、粉剤又は粒剤とする場合は０.０５
〜２０％（重量）、好ましくは０.１％〜１０％（重
量）の範囲から適宜選ぶのがよい。乳剤又は水和剤とす
る場合は０.５〜８０％（重量）、好ましくは１〜６０
％（重量）の範囲から適宜選ぶのがよい。The compounding ratio of the active ingredient is appropriately selected according to need, but in the case of powder or granules, it is 0.05
~ 20% (weight), preferably 0.1% to 10% (weight) in range. When used as an emulsion or wettable powder, it is 0.5 to 80% (weight), preferably 1 to 60%.
It is preferable to appropriately select from the range of% (weight).
【００４１】本発明の殺虫剤は茎葉散布、土壌施用、育
苗箱施用又は水面施用等により使用することができる。
使用に際しては適当な濃度に希釈して散布するか又は直
接施用する。本発明の殺虫剤の施用量は使用される化合
物の種類、対象害虫、発生傾向、被害の程度、環境条
件、使用する剤型などによってかわるが、粉剤及び粒剤
のようにそのまま使用する場合は有効成分として１０ア
ール当り０.０５g〜５Kg、好ましくは０.１g〜１Kgの範
囲から適宜選ぶのがよい。また、乳剤及び水和剤とする
場合のように液状で使用する場合は０.１〜５０００pp
m、好ましくは１〜１０００ppmの範囲から適宜選ぶのが
よい。The insecticide of the present invention can be used by foliage application, soil application, nursery box application or water surface application.
Before use, dilute to an appropriate concentration and spray or apply directly. The application rate of the insecticide of the present invention varies depending on the type of compound used, target pest, development tendency, degree of damage, environmental conditions, dosage form used, etc., but when used as it is as in powder and granules As an active ingredient, it may be appropriately selected from the range of 0.05 g to 5 kg, preferably 0.1 g to 1 kg per 10 ares. When used in liquid form, such as when used as an emulsion or wettable powder, it is 0.1 to 5000 pp.
m, preferably from 1 to 1000 ppm.
【００４２】本発明の殺虫剤は、他の殺虫剤、殺菌剤、
肥料、植物成長調製剤を混合して使用することもでき
る。The insecticide of the present invention includes other insecticides, fungicides,
A fertilizer and a plant growth regulator may be mixed and used.
【００４３】次に、代表的な製剤例を挙げて製剤方法を
具体的に説明するが化合物、添加剤の種類及び配合比率
はこれのみに限定されることなく広い範囲で変更可能で
ある。以下の説明において、％は重量百分率を示す。Next, the formulation method will be specifically described with reference to typical formulation examples, but the types and compounding ratios of the compounds and additives are not limited to these and can be varied within a wide range. In the following description,% indicates weight percentage.
【００４４】製剤例１ 乳剤 化合物（８）３０％、シクロヘキサノン２０％、ポリオ
キシエチレンアルキルアリールエーテル１１％、アルキ
ルベンゼンスルホン酸カルシウム４％及びメチルナフタ
リン３５％を均一に溶解して乳剤とした。これを水で希
釈して施用する。Formulation Example 1 Emulsion Compound (8) 30%, cyclohexanone 20%, polyoxyethylene alkylaryl ether 11%, calcium alkylbenzene sulfonate 4% and methylnaphthalene 35% were uniformly dissolved to obtain an emulsion. It is diluted with water and applied.
【００４５】製剤例２ 水和剤 化合物（９）４０％、珪藻土１５％、クレー１５％、ホ
ワイトカーボン２５％、ジナフチルメタンジスルホン酸
ナトリウム２％及びリグニンスルホン酸ナトリウム３％
を均一に混合粉砕して水和剤とした。これを水で希釈し
て施用する。Formulation Example 2 Wettable powder Compound (9) 40%, diatomaceous earth 15%, clay 15%, white carbon 25%, sodium dinaphthylmethanedisulfonate 2% and sodium ligninsulfonate 3%
Was uniformly mixed and pulverized to obtain a wettable powder. It is diluted with water and applied.
【００４６】製剤例３ 粉剤 化合物（２１）２％、珪藻土５％及びクレー９３％を均
一に混合粉砕して粉剤とした。これを直接施用する。Formulation Example 3 Dust Powder 2% of the compound (21), 5% of diatomaceous earth and 93% of clay were uniformly mixed and pulverized to obtain a powder. Apply this directly.
【００４７】製剤例４ 粒剤 化合物（３１）５％、ラウリルアルコール硫酸エステル
のナトリウム塩２％、リグニンスルホン酸ナトリウム５
％、カルボキシメチルセルロース２％及びクレー８６％
を均一に混合粉砕する。この混合物１００重量部に水２
０重量部を加えて練合し、押出式造粒機を用いて１４〜
３２メッシュの粒状に加工したのち、乾燥して粒剤とし
た。これを直接施用する。Formulation Example 4 Granules Compound (31) 5%, lauryl alcohol sulfate sodium salt 2%, sodium lignin sulfonate 5
%, Carboxymethylcellulose 2% and clay 86%
Are uniformly mixed and pulverized. 100 parts by weight of this mixture are mixed with 2 parts of water.
Add 0 parts by weight and knead.
It was processed into 32 mesh granules and then dried to obtain granules. Apply this directly.
【００４８】[0048]
【発明の効果】本発明の置換アルケニルケトン誘導体は
作物に悪影響を及ぼすことなく、種々の有害昆虫類、例
えばトビイロウンカ、セジロウンカ及びヒメトビウンカ
等のウンカ類、ツマグロヨコバイ及びミドリヒメヨコバ
イ等のヨコバイ類等の半翅目害虫、ワタアブラムシ、モ
モアカアブラムシ、ダイコンアブラムシ等のアブラムシ
類及びコナガ、ニカメイガ、シロイチモジヨトウ、ハス
モンヨトウ等の鱗翅目害虫、更にナミハダニ、カンザワ
ハダニ、ミカンハダニ等のハダニ類の防除に有効であ
る。特にトビイロウンカ、ツマグロヨコバイ等の水稲害
虫及びコナガ等の園芸害虫を殺滅防除することができ
る。INDUSTRIAL APPLICABILITY The substituted alkenyl ketone derivative of the present invention does not adversely affect crops, and can be used in various insect pests, for example, planthoppers such as brown planthopper, sedgerow planthopper, and planthopper planthopper, leafhoppers such as leafhopper leafhopper and leafhopper leafhopper. It is effective for the control of aphids such as pests of the order Thysanoptera, cotton aphid, aphid peach, aphid aphid, and pests of the order Lepidoptera such as diamondback moth, Nikamei moth, Spodoptera litura, and Spodoptera litura, as well as spider mites such as spider mites, kanzawa mites and citrus spider mites. In particular, it can kill and control paddy rice pests such as brown planthoppers and leafhoppers and horticultural pests such as diamondback moth.
【００４９】次に本発明化合物の奏する効果について試
験例をもって説明する。尚、いずれの試験においても効
果は以下の基準で評価した。また比較薬剤としては公知
化合物４−（２−ピリジルアミノ）−１,１,１−トリフ
ルオロ−２−ブテン−３−オン〔Zh. Org. Khim. ２６
巻、９号、１８７７頁（１９９０年）記載化合物〕を供
試化合物と同様に製剤して使用した。Next, the effect of the compound of the present invention will be described with reference to test examples. In each test, the effect was evaluated based on the following criteria. Further, as a comparative drug, a known compound 4- (2-pyridylamino) -1,1,1-trifluoro-2-buten-3-one [Zh. Org. Khim. 26
Vol. 9, No. 9, page 1877 (1990) described compound] was used in the same manner as the test compound.
【００５０】Ａは死虫率９０％〜１００％、Ｂは死虫率
７０％〜９０％未満、Ｃは死虫率５０％〜７０％未満、
Ｄは死虫率５０％未満を意味する。A is 90% to 100% mortality, B is 70% to less than 90% mortality, C is 50% to less than 70% mortality,
D means a mortality rate of less than 50%.
【００５１】試験例１ トビイロウンカ殺虫試験 製剤例２に準じて調製した水和剤を５００ppmの濃度に
水で希釈した。その薬液にイネ茎葉を浸漬し、風乾後、
試験管に静置した。その中にトビイロウンカ幼虫１０頭
を放ち、脱脂綿で栓をした。その後、２５℃の恒温室に
置き、６日後に死虫数を調査し、死虫率を算出した。試
験は２連制で行った。結果を表９に示す。Test Example 1 Testimony of brown planthopper insecticidal The wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 500 ppm. Dipping rice foliage in the drug solution, air-drying,
Placed in a test tube. Ten larvae of the brown planthopper were released therein and capped with absorbent cotton. After that, it was placed in a constant temperature room at 25 ° C., and after 6 days, the number of dead insects was investigated and the dead insect rate was calculated. The test was conducted in two consecutive cycles. The results are shown in Table 9.
【００５２】[0052]
【表９】 [Table 9]
【００５３】試験例２ ツマグロヨコバイ殺虫試験 製剤例２に準じて調製した水和剤を５００ppmの濃度に
水で希釈した。その薬液にイネ茎葉を浸漬し、風乾後、
試験管に静置した。その中にツマグロヨコバイ幼虫５頭
を放ち、脱脂綿で栓をした。その後、２５℃の恒温室に
置き、６日後に死虫数を調査し、死虫率を算出した。試
験は２連制で行った。結果を表１０に示す。Test Example 2 Black leafhopper insecticidal test A wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 500 ppm. Dipping rice foliage in the drug solution, air-drying,
Placed in a test tube. Five larvae of the leafhopper leafhoppers were released therein and capped with absorbent cotton. After that, it was placed in a constant temperature room at 25 ° C., and after 6 days, the number of dead insects was investigated and the dead insect rate was calculated. The test was conducted in two consecutive cycles. The results are shown in Table 10.
【００５４】[0054]
【表１０】 [Table 10]
【００５５】試験例３ ニカメイガ殺虫試験 製剤例２に準じて調整した水和剤を５００ppmの濃度に
水で希釈した。その薬液にイネ芽だし籾を浸漬し、濾紙
を入れた６０cc塩ビ製カップに静置した。その中にニカ
メイガ幼虫１０頭を放ち、フタをし２５℃の恒温室に置
き、６日後に死虫数を調査し、死虫率を算出した。試験
は２連制で行った。結果を表１１に示す。Test Example 3 Insecticidal test for Nikameiga A wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 500 ppm. Rice bud buds were soaked in the chemical solution and left still in a 60 cc vinyl chloride cup containing a filter paper. Ten larvae of the larvae of the larvae of the squid moth were released in it, placed in a lid and placed in a constant temperature room at 25 ° C., and after 6 days, the number of dead larvae was investigated and the mortality rate was calculated. The test was conducted in two consecutive cycles. The results are shown in Table 11.
【００５６】[0056]
【表１１】 [Table 11]
【００５７】試験例４ コナガ殺虫試験 製剤例２に準じて調整した水和剤を５００ppmの濃度に
水で希釈した。その薬液にキャベツ葉を浸漬し、風乾
後、濾紙を入れた６０cc塩ビ製カップに静置した。その
中にコナガ幼虫１０頭を放ち、フタをし２５℃の恒温室
に置き、６日後に死虫数を調査し、死虫率を算出した。
試験は２連制で行った。結果を表１２に示す。Test Example 4 Diamondback moth insecticidal test A wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 500 ppm. Cabbage leaves were dipped in the chemical solution, air-dried, and then left still in a 60 cc vinyl chloride cup containing filter paper. Ten diamondback moth larvae were released therein, covered with a lid and placed in a thermostatic chamber at 25 ° C., and after 6 days, the number of dead larvae was investigated and the mortality rate was calculated.
The test was conducted in two consecutive cycles. The results are shown in Table 12.
【００５８】[0058]
【表１２】 [Table 12]
【００５９】試験例５ ワタアブラムシ殺虫試験 製剤例２に準じて調製した水和剤を１００ppmの濃度に
水で希釈した。その薬液に、予めワタアブラムシ若虫を
接種しておいたキュウリ苗を浸漬し、風乾した。処理後
のキュウリ苗は２５℃の恒温室に置き、３日後に死虫数
を調査し、死虫率を算出した。試験は２連制で行った。
結果を表１３に示す。Test Example 5 Cotton Aphid Insecticidal Test A wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 100 ppm. Cucumber seedlings, which had been inoculated with cotton aphid nymphs in advance, were immersed in the drug solution and air-dried. The treated cucumber seedlings were placed in a constant temperature room at 25 ° C., and the number of dead insects was investigated 3 days later, and the dead insect rate was calculated. The test was conducted in two consecutive cycles.
The results are shown in Table 13.
【００６０】[0060]
【表１３】 [Table 13]
【００６１】[0061]
───────────────────────────────────────────────────── フロントページの続き (72)発明者 栗原 浩 静岡県小笠郡菊川町青葉台１丁目６番地の ４ (72)発明者 美濃口 直和 静岡県小笠郡菊川町加茂1809番地 (72)発明者 矢野 祐幸 静岡県小笠郡菊川町加茂1809番地 (72)発明者 平野 忠美 静岡県掛川市葛ヶ丘３丁目９番地の２ ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Hiroshi Kurihara 4-6-1, Aobadai, Kikugawa-cho, Ogasa-gun, Shizuoka Prefecture (72) Inventor Naokazu Minoguchi 1809 Kamo, Kikugawa-cho, Ogasa-gun, Shizuoka (72) Inventor Yuno Yano 1809 Kamo, Kikugawa-cho, Ogasa-gun, Shizuoka Prefecture (72) Inventor Tadami Hirano 2-9-3, Katsurugaoka, Kakegawa City, Shizuoka Prefecture
Claims (2)
示し、Ｒ3は分岐してもよいアルキル基又はフェニル基
（当該フェニル基はハロゲン原子、分岐してもよいアル
キル基、アルコキシ基又はハロアルキル基で置換されて
もよい。）を示し、Ｒ4は水素原子、分岐してもよいア
ルキル基及びハロアルキル基を示し、Ｚはピリジル基、
ピリミジニル基及びチアゾリル基（当該ピリジル基、ピ
リミジニル基及びチアゾリル基はハロゲン原子、分岐し
てもよいアルキル基、アルコキシ基又はハロアルキル基
で置換されてもよい。）、又は式 【化２】 （式中、Ｒ5、Ｒ6は水素原子、分岐してもよいアルキル
基及びハロアルキル基を示し、Ｒ5とＲ6は炭素数３〜７
の環を形成することもできる。Ｑはハロゲン原子、分岐
してもよいアルキル基、ハロアルキル基、アルコキシ
基、ハロアルコキシ基及びフェノキシ基より任意に選ば
れる置換基を有していてもよいフェニル基及び同様の置
換を有していてもよいピリジル基を示す。）で表される
基を示す。〕で表される置換アルケニルケトン誘導体。1. A general formula: [In the formula, R 1 represents a haloalkyl group, R 2 represents a hydrogen atom, and R 3 represents a branched alkyl group or a phenyl group (the phenyl group is a halogen atom, a branched alkyl group, an alkoxy group). Or a haloalkyl group), R 4 represents a hydrogen atom, an optionally branched alkyl group or a haloalkyl group, Z represents a pyridyl group,
A pyrimidinyl group and a thiazolyl group (the pyridyl group, the pyrimidinyl group and the thiazolyl group may be substituted with a halogen atom, an alkyl group which may be branched, an alkoxy group or a haloalkyl group), or a compound represented by the formula: (In the formula, R 5 and R 6 represent a hydrogen atom, an alkyl group and a haloalkyl group which may be branched, and R 5 and R 6 have 3 to 7 carbon atoms.
It is also possible to form a ring. Q has a halogen atom, an optionally branched alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group and a phenoxy group, which may have a substituent, and a similar substituent. Is a pyridyl group. ) Represents a group represented by. ] The substituted alkenyl ketone derivative represented by these.
導体を有効成分として含有することを特徴とする殺虫
剤。 【０００１】2. An insecticide containing the substituted alkenyl ketone derivative according to claim 1 as an active ingredient. [0001]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22365092A JP3283069B2 (en) | 1992-07-31 | 1992-07-31 | Substituted alkenyl ketone derivatives and insecticides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22365092A JP3283069B2 (en) | 1992-07-31 | 1992-07-31 | Substituted alkenyl ketone derivatives and insecticides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06135933A true JPH06135933A (en) | 1994-05-17 |
| JP3283069B2 JP3283069B2 (en) | 2002-05-20 |
Family
ID=16801511
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22365092A Expired - Fee Related JP3283069B2 (en) | 1992-07-31 | 1992-07-31 | Substituted alkenyl ketone derivatives and insecticides |
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| Country | Link |
|---|---|
| JP (1) | JP3283069B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104119268A (en) * | 2014-06-24 | 2014-10-29 | 济南大学 | Preparation and application of trifluoroacetyl anabasine compounds with insecticidal activity |
-
1992
- 1992-07-31 JP JP22365092A patent/JP3283069B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104119268A (en) * | 2014-06-24 | 2014-10-29 | 济南大学 | Preparation and application of trifluoroacetyl anabasine compounds with insecticidal activity |
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| Publication number | Publication date |
|---|---|
| JP3283069B2 (en) | 2002-05-20 |
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