JPS60237067A - N-benzoyl-n'-pyridyloxyalkylurea based compound and insecticide containing same - Google Patents
N-benzoyl-n'-pyridyloxyalkylurea based compound and insecticide containing sameInfo
- Publication number
- JPS60237067A JPS60237067A JP9143684A JP9143684A JPS60237067A JP S60237067 A JPS60237067 A JP S60237067A JP 9143684 A JP9143684 A JP 9143684A JP 9143684 A JP9143684 A JP 9143684A JP S60237067 A JPS60237067 A JP S60237067A
- Authority
- JP
- Japan
- Prior art keywords
- benzoyl
- based compound
- pyridyloxyalkylurea
- formula
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は新規なN−ベンゾイル−N1−ピリジルオキシ
アルキルウレア系化合物及びそれらを含有する殺虫剤に
関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel N-benzoyl-N1-pyridyloxyalkylurea compounds and insecticides containing them.
詳しくII′i、本発明は、一般式(1)、(式中、R
1#R1及びR8は水素原子又ハハロゲン原子であシ%
nは1〜5の整数である)で表わされるN−ベンゾイル
−V−ピリジルオキシアルキルウレア系化合物及びそれ
らを含有する殺虫剤である。In detail, II'i, the present invention relates to general formula (1), (wherein R
1#R1 and R8 are hydrogen atoms or hahalogen atoms%
N-benzoyl-V-pyridyloxyalkylurea compounds represented by (n is an integer of 1 to 5) and insecticides containing them.
前記一般式(1)のR,、R,及びR1で表わされるハ
ロゲン原子としては、弗素、塩素、臭素1沃素が挙けら
れる。Examples of the halogen atoms represented by R, , R, and R1 in the general formula (1) include fluorine, chlorine, and bromine-1-iodine.
本発明のN−ベンゾイル−N1−ピリジルオキシアルキ
ルウレア系化合物は、通常、一般式(It)、Rて
ド2
(式中b R1及びR1は前述の通シである)で表わさ
れるペンジイルイソシアネート系化合物と、一般式(釦
(式中、R8及びnけ前述の通シである)で表わされる
ピリジルオキシアルキルアミン系化合物とを1反応させ
ることによって製造される。この反応は、ベンゼン、ト
ルエン、キシレン、ピリジン、ジオキサン、ジメチルス
ルホキシドなどの溶媒の存在下に行なわれ1反応源度は
0〜200℃、反応時間は0.1〜24時間である。The N-benzoyl-N1-pyridyloxyalkyl urea compound of the present invention is usually a pendiyl isocyanate represented by the general formula (It), where R1 and R1 are as defined above. It is produced by reacting a pyridyloxyalkylamine compound with a pyridyloxyalkylamine compound represented by the general formula (in the formula, R8 and n are the same as above). The reaction is carried out in the presence of a solvent such as xylene, pyridine, dioxane or dimethyl sulfoxide, and the reaction temperature is 0 to 200°C and the reaction time is 0.1 to 24 hours.
なお、前記一般式(幻で表わされるピリジルオキシアル
キルアミン系化合物は、例えば下記の反応によって製造
することができる。The pyridyloxyalkylamine compound represented by the general formula (phantom) can be produced, for example, by the following reaction.
(■)
上記一般式(IV) mvll)中のR3及びnは前述
の通シである。(■) R3 and n in the above general formula (IV) mvll) are as defined above.
次に、本発明化合物の具体的合成例を記載する。Next, specific synthesis examples of the compounds of the present invention will be described.
合成例
(11N−(3−ヒドロキシプロピル)フタルイミド3
.0gをテトラヒドロフラン20ゴに溶解し、水冷下水
素化ナトリウム0.32 gを加え、30分間攪拌した
後、2.3−ジクロロ−5−トリフルオロメチルピリジ
ン2.99gを加え、室温で1.5時間攪拌し、さらに
40℃で3時間攪拌して反応させた。Synthesis example (11N-(3-hydroxypropyl)phthalimide 3
.. 0 g was dissolved in 20 g of tetrahydrofuran, 0.32 g of sodium hydride was added under water cooling, and after stirring for 30 minutes, 2.99 g of 2.3-dichloro-5-trifluoromethylpyridine was added, and the solution was dissolved at room temperature to 1.5 g. The mixture was stirred for an hour, and further stirred at 40° C. for 3 hours to react.
反応混合物を水中に投入し、生じた固体を戸数して、N
−(3−(3−クロロ−5−トリフルオロメチル−2−
ピリジルオキシ)プロピル〕フタルイミド3、Ogを得
た。The reaction mixture was poured into water, the resulting solid was counted, and N
-(3-(3-chloro-5-trifluoromethyl-2-
Pyridyloxy)propyl]phthalimide 3, Og was obtained.
(2) 前記(11工程で得た置換フタルイミド2.8
0g、ヒドラジンヒドラ−) 1.411Ll及びエタ
ノール20dの混合物を20分間還流下に反応させた後
、沖過し、F液を減圧濃縮し、残渣に塩化メチレンを加
え、不溶物をp過して除いた。得られたF液を水洗し、
無水硫酸ナトリウムで乾燥した後、溶媒を留去して、融
点79〜83℃の2−(3−了ミノプロボキシ)−3−
クロロ−5−トリフルオロメチルビIJ シン1.67
gを得た。(2) Substituted phthalimide 2.8 obtained in step 11 above
After reacting a mixture of 1.411L (0g, hydrazine hydra) and 20d of ethanol under reflux for 20 minutes, it was filtered, the F solution was concentrated under reduced pressure, methylene chloride was added to the residue, and insoluble matter was filtered. Excluded. The obtained F solution was washed with water,
After drying over anhydrous sodium sulfate, the solvent was distilled off to give 2-(3-minoproxy)-3- with a melting point of 79-83°C.
Chloro-5-trifluoromethylbi IJ Syn 1.67
I got g.
(3)前記(2)工程で得た置換トリフルオロメチルピ
リジン0.33 gをジオキサン81IIlに溶解し2
.6−シフルオロペンゾイルインシアネー)0.24g
のジオキサン溶液5dを加え、室温で15時間攪拌して
反応させた。反応混合物を水中に投入し、塩化メチレン
で抽出し、抽出層を水洗し、無水硫酸ナトリウムで乾燥
した後、溶媒を留去して、融点140−143℃のN−
(2,6−ジフルオロベンゾイル)N’−(3−(3−
クロロ−5−トリフルオロメチル−2−ピリジルオキシ
)プロピルツウレア0.40 gを得た。(3) 0.33 g of substituted trifluoromethylpyridine obtained in step (2) above was dissolved in 81IIl of dioxane, and 2
.. 6-cyfluoropenzoyl incyane) 0.24g
5d of dioxane solution was added thereto, and the mixture was stirred at room temperature for 15 hours to react. The reaction mixture was poured into water, extracted with methylene chloride, the extracted layer was washed with water, dried over anhydrous sodium sulfate, the solvent was distilled off, and N-
(2,6-difluorobenzoyl)N'-(3-(3-
0.40 g of chloro-5-trifluoromethyl-2-pyridyloxy)propylturea was obtained.
前記一般的製法及び具体的合成法に準じて製造された化
合物の具体的代表例を記載する。Specific representative examples of compounds produced according to the above-mentioned general production method and specific synthesis method will be described.
本発明化合物は、後記試験例にみる通夛、殺虫剤、特に
殺昆虫剤の有効成分として優れた活性を示す。The compound of the present invention exhibits excellent activity as an insecticide, particularly as an active ingredient of an insecticide, as shown in the test examples described below.
このものを殺虫剤の有効成分として使用するに際しては
、従来の農薬の製剤の場合と同様に農薬補助剤と共に乳
剤、粉剤、水利剤、液剤などの種々の形態に製剤するこ
とができる。これらの製剤の実際の便甲に際しては、そ
のまま便甲するか、または水等の希釈剤で所定濃度に希
釈して使用することができる。When this product is used as an active ingredient of an insecticide, it can be formulated into various forms such as emulsions, powders, water preparations, and liquids together with pesticide adjuvants, as in the case of conventional pesticide formulations. When actually using these preparations, they can be used as is, or after being diluted to a predetermined concentration with a diluent such as water.
ここに15農薬補助剤としては、メルク、カオリン、ベ
ントナイト、珪藻土、ホワイトカーボン、クレー、澱粉
などの固型担体、水、トルエン、キシレン、クロロベン
ゼン、シクロヘキサン、ジメチルスルホキシド、ジメチ
ルホルム了ミド、アルコールなどの液体希釈剤、乳化剤
、分散剤、展着剤などを挙げることができる。また必要
に応じて他の農薬、例えば殺虫剤、殺ダニ剤、殺菌剤、
植物生長調整剤などと混用、併用することができ、この
場合に一層優れた効果を示すこともある。15 Pesticide adjuvants include solid carriers such as Merck, kaolin, bentonite, diatomaceous earth, white carbon, clay, starch, water, toluene, xylene, chlorobenzene, cyclohexane, dimethyl sulfoxide, dimethylformide, alcohol, etc. Examples include liquid diluents, emulsifiers, dispersants, and spreading agents. In addition, other agricultural chemicals such as insecticides, acaricides, fungicides,
It can be mixed or used in combination with plant growth regulators, etc., and may exhibit even better effects in this case.
不発甲の殺虫剤Fi種々の有害虫、特に有害昆虫の防除
に有効であり、施用は一般に1〜10.0(10ppm
、望ましく tit 20〜2,000 ppmの有効
成分濃度で行なう。また家畜に対して前記有効成分を飼
料に混合して与え、その***物での有害虫、特に有害昆
虫の発生、生育を防除したシ或いは、昆虫の成虫に有効
成分を処理することによって卵のふ化を阻止することも
できる。なお、水棲有害虫の場合は、上記の濃度範囲の
薬液を発生場所に散布して防除できることから、水中で
の薬液濃度範囲に上記以下でも有効である。Insecticide Fi for unexploded carapace is effective in controlling various harmful insects, especially harmful insects, and is generally applied at a concentration of 1 to 10.0 (10 ppm).
, preferably at an active ingredient concentration of 20 to 2,000 ppm. In addition, the above-mentioned active ingredients can be mixed with livestock feed to control the emergence and growth of harmful insects, especially harmful insects, in their excrement, or eggs can be reduced by treating adult insects with the active ingredients. It can also prevent hatching. In the case of harmful aquatic insects, it is possible to control them by spraying a chemical solution in the above concentration range to the place where they occur, so it is also effective even if the concentration range of the chemical solution in water is less than the above range.
試験例1
有効成分化合物の製剤品を水に分散させ、800 pp
mの濃度に調整した薬液にキャベツの葉片を約10秒間
浸漬し、取シ出して風乾した。ベトリ皿(直径9cm)
に湿ったp紙を敷き、その上に葉片を置すた。そこへ2
〜3令のハスモンヨトウの幼虫を放ち、ふたをして28
℃の照明付恒温器内に放置した。放虫後8日目に生死を
判定し、下記の計算式により死去率をめて第1表の結果
を得た。 (第1表
試験例2
2〜3令のハスモンヨトウを2〜3令のコナガに、及び
有効成分の濃度、800ppmを10ppmに代えるこ
と以外は、化合物N091を用いて前記試験例1の場合
と同様にしたところ、死去率〜は100であった。Test Example 1 A formulation of the active ingredient compound was dispersed in water, and 800 pp.
A cabbage leaf piece was immersed in a chemical solution adjusted to a concentration of m for about 10 seconds, taken out, and air-dried. Veterinary dish (9cm diameter)
A damp p paper was placed on top of the paper, and the leaf pieces were placed on top of it. There 2
~ Release 3rd instar Spodoptera larvae and cover with a lid.
It was left in a thermostat with lighting at ℃. On the 8th day after the release of the insects, whether they were alive or dead was determined, and the mortality rate was calculated using the following formula to obtain the results shown in Table 1. (Table 1 Test Example 2 The same as in Test Example 1 using compound N091, except that the 2nd to 3rd instar Spodoptera were replaced with 2nd to 3rd instar diamondback moths, and the concentration of the active ingredient was changed from 800 ppm to 10 ppm. The mortality rate was 100.
製剤例1
(イ)化合物NO,120朋i1%63(ロ)ジ−クラ
イト 72重量部
(ハ) リグニンスルホン酸ソーダ 8m以上のものを
均一に混合して水利剤とした。Formulation Example 1 (a) Compound No. 120 i1% 63 (b) Diquerite 72 parts by weight (c) Sodium ligninsulfonate 8 m or more were uniformly mixed to prepare an irrigation agent.
製剤例2 (イ)化合物N O,35重社部 (→タルク 95廁園 以上のものを均一に混合して粉剤とした。Formulation example 2 (a) Compound N O, 35 Jushabu (→Talc 95 Liaoyuan The above ingredients were mixed uniformly to form a powder.
製剤例3
(イ)化合物NO,220重量部
(→ N、NLジメチルホルム了ξド 70重量部C3
ポリオキシエチレンアルキルフェニルエーテル i o
1101000ものを均一に混合、溶解して乳剤とした
。Formulation Example 3 (a) Compound NO, 220 parts by weight (→ N, NL dimethylform) 70 parts by weight C3
Polyoxyethylene alkylphenyl ether io
1,101,000 were uniformly mixed and dissolved to form an emulsion.
製剤例4
(イ) ジ−クライト 78朋i6
(ロ) β−ナフタレンスルも2俊ソーダホルマリン縮
−1i 2重枇C→ ポ11オキシエチレンアルキル了
リルサルフエー) 5ffi部に)ホワイトカーボン
15重計部
以上の各成分の混合物と、化合物NO,1とを、4:1
の重量割合で混合し、水利剤とした。Formulation Example 4 (a) Si-cryte 78 i6 (b) β-naphthalene sulfate 2-chloride formalin condensed-1i 2-fold C→po-11 oxyethylene alkyl ryol sulfate) 5ffi part) white carbon
15 weight parts or more of a mixture of each component and compound NO.1 in a 4:1 ratio
The mixture was mixed in a weight ratio of
特許出願人 石原産業株式会社Patent applicant: Ishihara Sangyo Co., Ltd.
Claims (1)
原子であり、nは1〜5の整数である)で表わされるN
−ベンゾイル−Nl−ピリジルオキシアルキルウレア系
化合物。 2一般式 (式中%R,,R,及びR8は水素原子又はハロゲン原
子であプ、nは1〜5の整数である)で表わされるN−
ベンゾイル−N1−ピリジルオキシアルキルウレア系化
合物の少くとも一種を有効成分として含有することを特
徴とする殺虫剤。[Claims] N represented by the general formula (wherein % R1sR2 and R1 are hydrogen atoms or halogen atoms, and n is an integer from 1 to 5)
-Benzoyl-Nl-pyridyloxyalkylurea compound. 2 N- represented by the general formula (in the formula, %R, , R, and R8 are hydrogen atoms or halogen atoms, and n is an integer from 1 to 5)
An insecticide characterized by containing at least one type of benzoyl-N1-pyridyloxyalkylurea compound as an active ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP9143684A JPS60237067A (en) | 1984-05-08 | 1984-05-08 | N-benzoyl-n'-pyridyloxyalkylurea based compound and insecticide containing same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP9143684A JPS60237067A (en) | 1984-05-08 | 1984-05-08 | N-benzoyl-n'-pyridyloxyalkylurea based compound and insecticide containing same |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS60237067A true JPS60237067A (en) | 1985-11-25 |
Family
ID=14026314
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP9143684A Pending JPS60237067A (en) | 1984-05-08 | 1984-05-08 | N-benzoyl-n'-pyridyloxyalkylurea based compound and insecticide containing same |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS60237067A (en) |
-
1984
- 1984-05-08 JP JP9143684A patent/JPS60237067A/en active Pending
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