JPH02223549A - Sulfinic acid derivative, production thereof and composition thereof - Google Patents
Sulfinic acid derivative, production thereof and composition thereofInfo
- Publication number
- JPH02223549A JPH02223549A JP1023789A JP1023789A JPH02223549A JP H02223549 A JPH02223549 A JP H02223549A JP 1023789 A JP1023789 A JP 1023789A JP 1023789 A JP1023789 A JP 1023789A JP H02223549 A JPH02223549 A JP H02223549A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- salt
- compound
- acid
- sulfinic acid
- 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
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- 150000003452 sulfinic acid derivatives Chemical class 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 4
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- 150000003839 salts Chemical class 0.000 claims abstract description 36
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 3
- 125000001424 substituent group Chemical group 0.000 claims description 11
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- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
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- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、植物加害昆虫、動植物寄生性ダニ類、衛生害
虫などに対する優れた効力を有すスルフィン酸誘導体、
その製造法および殺虫殺ダニ剤に関する。DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to sulfinic acid derivatives having excellent efficacy against plant-damaging insects, animal and plant parasitic mites, sanitary pests, etc.
The present invention relates to its production method and insecticide and acaricide.
従来の技術
従来から多種の有害生物防除効果を有する合成化合物が
殺虫剤として使用されているが、その大部分のものは有
機リン酸エステル、カルバミン酸エステルあるいは有機
塩素化合物に属している。BACKGROUND OF THE INVENTION Conventionally, synthetic compounds having various pest control effects have been used as insecticides, but most of them belong to the organic phosphate esters, carbamate esters, or organic chlorine compounds.
このように限られた範囲の化合物が多用されることによ
って、たとえば害虫の殺虫剤抵抗性の増大などの弊害が
起こることは周知のとおりであり、また上記殺虫剤のう
ちのいくつかのものは、殺虫力が大きくても人畜毒性や
魚毒性が高く、ときには害虫の天敵に対しても毒性を表
し、予期しない害虫の大発生が起こるなど、実用上は必
ずしも満足できる効果が得られていないのが現状である
。It is well known that the frequent use of such a limited range of compounds causes harmful effects such as increased insecticide resistance in insect pests, and some of the above insecticides Although they have great insecticidal power, they are highly toxic to humans and animals, and are sometimes toxic to the natural enemies of pests, resulting in unexpected outbreaks of pests. is the current situation.
発明が解決しようとする課題
本発明の目的は、害虫の殺虫剤抵抗性の増大を回避でき
るような有機リン酸エステル、カルバミン酸エステルお
よび有機塩素化合物などの従来の殺虫剤の主流とは系統
が異なる新規構造を有し、かつ植物に対する薬害や人畜
毒性、魚毒性が低い新規殺虫殺ダニ剤を提供することに
ある。Problems to be Solved by the Invention The purpose of the present invention is to develop a system that is different from the mainstream of conventional insecticides such as organophosphate esters, carbamates, and organochlorine compounds, which can avoid the increase in insecticide resistance of insect pests. The object of the present invention is to provide a new insecticide and acaricide that has a new and different structure and has low drug toxicity to plants, toxicity to humans and animals, and toxicity to fish.
課題を解決するための手段
本発明者らは、工業的に有利に製造し得て、しかも植物
に対する薬害がなく、かつ温血動物や魚類に対する毒性
が低く安全に使用しうる殺虫殺ダニ剤について鋭意研究
を続けたところ、下記一般式（１）で示される化合物の
創製に成功するとともに、これらが各種の植物加害昆虫
、動植物寄生ダニ類、衛生害虫などに対して優れた殺虫
殺ダニ作用を有すると共に、温血動物や、魚類に対して
毒性が低く、しかも工業的にも有利に得られることを知
見し、さらにこれらの知見に基づき種々検討を加えた結
果本発明を完成するに至った。Means for Solving the Problems The present inventors have developed an insecticide and acaricide that can be industrially advantageously produced, has no phytotoxicity to plants, has low toxicity to warm-blooded animals and fish, and can be used safely. Through intensive research, we succeeded in creating compounds represented by the following general formula (1), and discovered that these compounds have excellent insecticidal and acaricidal effects against various plant-damaging insects, animal and plant parasitic mites, and sanitary pests. The present inventors have found that the present invention has a low toxicity to warm-blooded animals and fish, and can be obtained industrially advantageously.Based on these findings, various studies were conducted, and as a result, the present invention was completed. .
即ち本発明は、
（１）式
［式中、Ｒ区及びＲ１はそれぞれ水素原子又は置換基を
有していてもよい炭化水素残基を示すか、あるいはＲ１
とＲ１が一緒になって隣接する窒素原子とともに環を形
成していてもよく、Ｒ３は電子吸引性基を有するアルキ
ル基、又は式 Ｒ’ｌ（式中、Ｒ′″は置換基を有して
いてもよい炭化水素残基を示す。）で表わされる基を示
す。］で表わされるスルフィン酸誘導体（以下、単に化
合物（１）と称することがある。）またはその塩、
（２）式
［式中、Ｒ１、Ｒ２は上記した意義通り。］で表わされ
る化合物又はその塩と、式
％式％（）
［式中、Ｒ３は上記した意義通り。］で表わされる化合
物、またはその塩を反応させることを特徴とする上記式
（１）で表わされるスルフィン酸誘導体またはその塩の
製造法、及び
（３）上記一般式（１）で示されるスルフィン酸誘導体
またはその塩を含有することを特徴とする殺虫殺ダニ組
成物に関する。That is, the present invention is based on the formula (1) [wherein R group and R1 each represent a hydrogen atom or a hydrocarbon residue which may have a substituent,
and R1 may be taken together to form a ring with the adjacent nitrogen atom, and R3 is an alkyl group having an electron-withdrawing group, or R'l (wherein R''' has a substituent and A sulfinic acid derivative (hereinafter sometimes simply referred to as compound (1)) or a salt thereof, represented by the formula (2) [In the formula, R1 and R2 are as defined above], or a salt thereof is reacted with a compound represented by the formula %Formula% () [wherein, R3 is as defined above], or a salt thereof. and (3) a method for producing a sulfinic acid derivative represented by the above general formula (1) or a salt thereof, characterized by containing the sulfinic acid derivative represented by the above general formula (1) or a salt thereof. The present invention relates to an insecticidal and acaricidal composition.
上記式（１）において、Ｒ’、Ｒ’は同一または相異な
って水素原子または置換基を有していてもよい炭化水素
残基を示すかまたは、Ｒ１、Ｒ１は互いに結合して隣接
する窒素原子と共に環を形成してもよい。炭化水素残基
としては、例えばメチル、エチル、プロピル、イソプロ
ピル、ブチル、イソブチル、第ニブチル、第三ブチル、
ペンチル、ヘキシル、ヘプチル、オクチル、ノニル、デ
シル、ウンデシル、ドデシル、トリデシル、テトラデシ
ル、ペンタデシル等の炭素数１〜１５の直鎖又は分枝状
のアルキル、シクロプロパン、シクロブタン、シクロペ
ンクン、シクロへ牛すン等ノ炭素数３〜６のシクロアル
キル、例えばビニル、アリル、２−メタリル、３−メタ
リル、３−ブテニル等の炭素数２〜４のアルケニル、シ
クロプロペニル、シクロペンテニル、シクロへキセニル
等の炭素数３〜６のシクロアルケニル、例えばフェニル
、ナフチル等の炭素数６〜１０のアリール、例えばベン
ジル、フェニルエチル等の炭素数７〜１０のアラルキル
が用いられる。これら炭化水素残基は１ないし数個好ま
しくは１〜３個の置換基を有していてもよく、置換基と
してはニトロ、アミン、水酸基、シアノ、カルバモイル
、カルボキシル、スルホニル、例えば塩素、臭素、ヨウ
素等のハロゲン、例えばメトキシ、エトキシ、プロポキ
シ、インプロポキシ、ブトキシ、インブトキシ、第二ブ
トキシ、第三ブトキシ等の炭素数１〜４の低級アルコキ
ン、フェノキシ、ベンゾイル等があげられる。さらに、
これらの置換基で１〜３個置換されていてもよいＲ’
Ｒ’で表わされる炭化水素残基の例として」二に述べた
如きアリール、アラルキル、シクロアルキル等が置換し
ていてもよい。Ｒ１゜Ｒ２がいっしょになって隣接する
窒素原子と共に形成する環としては、たとえばピペラジ
ノ、モルホリノ、ピロリシフ等の５〜６員環状アミン基
が挙げられ、これらの環状アミ７基はたとえばＲＩ。In the above formula (1), R' and R' are the same or different and represent a hydrogen atom or a hydrocarbon residue which may have a substituent, or R1 and R1 are bonded to each other and the adjacent nitrogen A ring may be formed together with the atoms. Examples of hydrocarbon residues include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, nibutyl, tertiary butyl,
Straight chain or branched alkyl having 1 to 15 carbon atoms such as pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, cyclopropane, cyclobutane, cyclopenkune, cyclohexane cycloalkyl having 3 to 6 carbon atoms, alkenyl having 2 to 4 carbon atoms such as vinyl, allyl, 2-methallyl, 3-methallyl, 3-butenyl, cyclopropenyl, cyclopentenyl, cyclohexenyl, etc. Cycloalkenyl having 3 to 6 carbon atoms, aryl having 6 to 10 carbon atoms such as phenyl and naphthyl, and aralkyl having 7 to 10 carbon atoms such as benzyl and phenylethyl are used. These hydrocarbon residues may have one to several, preferably one to three, substituents, such as nitro, amine, hydroxyl, cyano, carbamoyl, carboxyl, sulfonyl, such as chlorine, bromine, Examples include halogens such as iodine, lower alkokenes having 1 to 4 carbon atoms such as methoxy, ethoxy, propoxy, impropoxy, butoxy, imbutoxy, sec-butoxy, tertiary-butoxy, phenoxy, benzoyl, and the like. moreover,
R' which may be substituted with 1 to 3 of these substituents
Examples of the hydrocarbon residue represented by R' may be substituted with aryl, aralkyl, cycloalkyl, etc. as described in 2. Examples of the ring formed by R1°R2 together with the adjacent nitrogen atom include 5- to 6-membered cyclic amine groups such as piperazino, morpholino, and pyrolisif, and these cyclic amine groups include, for example, RI.
Ｒ２について上記したアルキル基のうち炭素数１〜６の
低級アルキル基、ハロゲン、水酸基等で１〜４個置換さ
れていてもよい。Among the alkyl groups described above for R2, 1 to 4 may be substituted with a lower alkyl group having 1 to 6 carbon atoms, a halogen, a hydroxyl group, or the like.
Ｒ’、 Ｒ”としては、少なくとも一方が水素原子でな
い方が通常好ましい。とりわけＲ’、 Ｒ”とも炭化水
素残基であるのが好ましく、特にＲｌ、 Ｒ１ともにア
ルキル基である場合が好ましい。It is usually preferable that at least one of R' and R'' is not a hydrogen atom. In particular, it is preferable that both R' and R'' are hydrocarbon residues, and it is particularly preferable that both R1 and R1 are alkyl groups.
また」二記一般式において、Ｒ３で表わされる電子吸引
性基を有するアルキル基におけるアルキル基としては、
Ｒ’、 Ｒ２について前記したアルキル基のうち炭素数
１〜６のものが通常好ましい。とりわけメチル基が好ま
しい又これらアルキル基が有する電子吸引性基としては
、「分子内で水素を標準としたとき、他から電子を引き
つける傾向のある基」ならいずれの基でもよく、例えば
、二１・ロ基、シアノ基、トリフルオロメチル基、カル
ボキシル基、ハロゲン、エステル化されたカルボキシル
基（例、メトキシカルボニル、エトキシカルボニル。In addition, in the general formula 2, the alkyl group in the alkyl group having an electron-withdrawing group represented by R3 is:
Among the alkyl groups described above for R' and R2, those having 1 to 6 carbon atoms are usually preferred. A methyl group is particularly preferred, and the electron-withdrawing group possessed by these alkyl groups may be any group that has a tendency to attract electrons from other sources when hydrogen is used as a standard in the molecule.For example, 21・Ro group, cyano group, trifluoromethyl group, carboxyl group, halogen, esterified carboxyl group (e.g., methoxycarbonyl, ethoxycarbonyl).
フェノキシカルボニル）、−３ｏ、Ｒ（Ｒ：Ｃ，、アル
キル、フェニル等）、Ｒ１，ＲＲで述べた如き炭化水素
残基で置換されていてもよいカルバモイル基、−〇 Ｏ
Ｒ（Ｒは前記と同意義）で表わされる基などかあ１ｆら
れる。phenoxycarbonyl), -3o, R (R:C, alkyl, phenyl, etc.), R1, a carbamoyl group optionally substituted with a hydrocarbon residue as described in RR, -〇 O
A group represented by R (R has the same meaning as above), etc.
Ｒ３で表わされる電子吸引性基を有するアルキル基は、
特に上述したような電子吸引性基を、２個乃至３個有し
ているものが好ましい。The alkyl group having an electron-withdrawing group represented by R3 is
Particularly preferred are those having two to three electron-withdrawing groups as described above.
Ｒ４で表わされる置換基を有していてもよい炭化水素残
基としては、Ｒ’、 Ｒ’で上記した炭化水素残基があ
げられ、その置換基としても、上記した置換基があげら
れる。さらにＲ４で表わされる炭化水素残基は置換基と
して、上記式（Ｉ）からＲ３を除いた残りの基であって
もよい。この場合式（１）で表わされるスルフィン酸誘
導体は二量体となっている化合物等が含まれる。Ｒ４で
表わされる置換されていてもよい炭化水素残基としては
、上記したもののうち、とりわけＣ＋−ｅアルキル。Examples of the hydrocarbon residue which may have a substituent represented by R4 include the hydrocarbon residues described above for R' and R', and examples of the substituent include the above-mentioned substituents. Furthermore, the hydrocarbon residue represented by R4 may be a substituent that remains after removing R3 from the above formula (I). In this case, the sulfinic acid derivative represented by formula (1) includes compounds in the form of dimers. The optionally substituted hydrocarbon residue represented by R4 is particularly C+-e alkyl among those listed above.
Ｃ３−４アルケニル＋Ｃ７−１０アラルキル、及び式（
１）からＲ３を除いた残りの基等が好ましい。C3-4 alkenyl + C7-10 aralkyl, and the formula (
The remaining groups after removing R3 from 1) are preferred.
また、化合物（１）の塩としては、ナトリウム、マグネ
シウム、カリウム、カルシウム等のアルカリ金属、アル
カリ土類金属と形成する塩や、第四級アンモニウム塩あ
るいは、アミン基において形成される、たとえば塩酸、
リン酸、硫酸などの鉱酸、例えばシュウ酸、酢酸、安息
香酸などの有機酸との塩か挙げられる。Salts of compound (1) include salts formed with alkali metals and alkaline earth metals such as sodium, magnesium, potassium, and calcium, quaternary ammonium salts, and salts formed with amine groups, such as hydrochloric acid,
Examples include salts with mineral acids such as phosphoric acid and sulfuric acid, and organic acids such as oxalic acid, acetic acid, and benzoic acid.
本願の目的化合物（１）は、次のごとき方法等によって
製造することが出来る。The object compound (1) of the present application can be produced by the following method.
すなわち、式
１式中、各記号は前義の通りである。］で表わされる化
合物又はその塩と、式
％式％（）
［式中、各記号は前義の通りである。］で表わされる化
合物又はその塩とを反応させて化合物（１）またはその
塩は製造することができる。That is, in Formula 1, each symbol is as defined above. ] or a salt thereof, and a compound represented by the formula % formula % () [wherein each symbol is as defined above]. Compound (1) or a salt thereof can be produced by reacting with a compound represented by the following formula or a salt thereof.
ここで化合物（ｎ）の塩としては化合物（１）と同様ア
ミノ基において形成される、たとえば塩酸、リン酸、硫
酸などの鉱酸、例えばシュウ酸、酢酸、安息香酸などの
有機酸との塩があげられる。Here, the salts of compound (n) include salts formed at the amino group with mineral acids such as hydrochloric acid, phosphoric acid, and sulfuric acid, and organic acids such as oxalic acid, acetic acid, and benzoic acid, which are formed at the amino group as in compound (1). can be given.
さらに詳しくは、化合物（ＩＩ）と化合物（ＩＩＩ）と
を、無溶媒あるいは適当な溶媒中で反応させる。適当な
溶媒としては例えばメチルアルコール、エチルアルコー
ル、ｎ−プロピルアルコール、イソプロビルアルコーノ
ペｎ−ブチルアルコール、ｔｅｒｔブチルアルコール等
のアルコール類、ベンゼン、トルエン、キシレン等の芳
香族炭化水素類、塩化メチレン、クロロホルム、四塩化
炭素等のノ＼ロゲン化炭化水素類、エチルエーテル、ジ
オキサン、テトラヒドロフラン等のエーテル類、アセト
ン、メチルエチルケトン等のケトン類、アセトニトリル
、プロピオニトリル等のニトリル類、ジメチルフォルム
アミド、ジメチルアセトアミド等のアミド類、酢酸メチ
ル、酢酸エチル、酢酸ブチル等のエステル類が単独でま
たは混合して用いられる。More specifically, compound (II) and compound (III) are reacted without a solvent or in an appropriate solvent. Suitable solvents include, for example, alcohols such as methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropylalkone n-butyl alcohol, and tert-butyl alcohol, aromatic hydrocarbons such as benzene, toluene, and xylene, and methylene chloride. , chlorinated hydrocarbons such as chloroform and carbon tetrachloride, ethers such as ethyl ether, dioxane and tetrahydrofuran, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, dimethylformamide, dimethyl Amides such as acetamide, esters such as methyl acetate, ethyl acetate, butyl acetate, etc. are used alone or in combination.
また、要すれば水と芳香族炭化水素類、またはハロゲン
化炭化水素類との組み合わせを用いることもできる。Further, if necessary, a combination of water and aromatic hydrocarbons or halogenated hydrocarbons can be used.
本反応において化合物（Ｉ）は化合物（Ｉｆ）に対して
約１〜４倍モル、好ましくは約１２〜２．５倍モル用い
る。本反応温度は−７０〜１００’Ｃ好ましくは一５〜
８０°Ｃである。反応時間は反応温度等により異なるが
通常１５分〜１５時間、好適には、３０分〜８時間程度
である。このようにして得られた化合物（１）は、再結
晶、シリカゲルクロマトグラフィー（メルク製キーゼル
ゲル６０、溶出溶媒：クロロホルム、酢酸エチルエステ
ル等）等の自体公知の手段により遊離塩基として単離精
製するか、あるいは常法に従って、塩酸、硫酸、リン酸
等の無機酸、または酢酸、ベンゼンスルホン酸、ｐ−ト
ルエンスルホン酸、メタンスルホン酸、クエン酸、酒石
酸、シュウ酸、プロピオン酸、マレイン酸、リンゴ酸、
マロン酸、フマル酸、マンデル酸、アスコルビン酸等の
有機酸との付加塩として単離精製される。さらに、常法
に従って、スルフィン酸と前記したようなアルカリ金属
や、アルカリ土類金属または、有機アミン類との塩にす
ることによって単離精製することができる。In this reaction, Compound (I) is used about 1 to 4 times the mole of Compound (If), preferably about 12 to 2.5 times the mole of Compound (If). The reaction temperature is -70 to 100'C, preferably -5 to 100'C.
It is 80°C. The reaction time varies depending on the reaction temperature, etc., but is usually about 15 minutes to 15 hours, preferably about 30 minutes to 8 hours. Compound (1) thus obtained can be isolated and purified as a free base by means known per se, such as recrystallization, silica gel chromatography (Merck Kieselgel 60, elution solvent: chloroform, acetic acid ethyl ester, etc.). or inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, or acetic acid, benzenesulfonic acid, p-toluenesulfonic acid, methanesulfonic acid, citric acid, tartaric acid, oxalic acid, propionic acid, maleic acid, malic acid, etc., according to a conventional method. ,
It is isolated and purified as an addition salt with organic acids such as malonic acid, fumaric acid, mandelic acid, and ascorbic acid. Furthermore, it can be isolated and purified by forming a salt of sulfinic acid with an alkali metal, an alkaline earth metal, or an organic amine as described above according to a conventional method.
このようにして製造される本発明化合物（Ｉ）、または
その塩は植物加害昆虫、動植物寄生性ダニ類、衛生害虫
等に対し強い殺虫殺ダニ作用を有し、これら害虫の防除
に有効である。これら害虫の防除にあたっては、害虫の
寄生する動植物に直接散布するなど、昆虫に直接接触さ
せることによっても達成できるが、一方、より特徴のあ
る性質としては、薬剤を根、葉、茎等から植物に一旦吸
収させた後、この植物を害虫が吸汗、川明するか、ある
いはこれに接触することによっても強い殺虫作用を示す
点にある。このような性質は吸汗性、粗食性の昆虫ある
いはダニ類を駆除するために有利である。又、本発明の
化合物は植物に対する薬害も少なく、かつ魚類に対する
毒性も低いなど、農業用害虫防除剤として安全でかつ有
利な性質を併せ持っている。The compound (I) of the present invention or a salt thereof produced in this manner has a strong insecticidal and acaricidal effect against plant-damaging insects, parasitic mites on animals and plants, sanitary pests, etc., and is effective in controlling these pests. . Control of these pests can also be achieved by direct contact with the insects, such as by directly spraying them on plants and animals infested by the pests. Once absorbed by the plant, pests exhibit a strong insecticidal effect when they sweat, evaporate, or even come into contact with the plant. Such properties are advantageous for exterminating sweat-absorbing, coarse-feeding insects and mites. Furthermore, the compound of the present invention has both safe and advantageous properties as an agricultural pest control agent, such as having little phytotoxicity to plants and low toxicity to fish.
より詳しくは、本発明化合物（Ｉ）ならびにそれを含有
する製剤は、たとえば、ヒメトビウンカ（Ｌａｏｄｅｌ
ｐｈａｘ ５ｔｉａｔｅｌｌｕｓｓ）、ツマグロヨコ
ノぐイ（Ｎｅｐｈｏｔｅｔｔｉｘ ｃｉｎｃｔｉｃｅ
ｐｓ）、ヤノネカイガラムシ（Ｕｎａｓｐｉｓ ｙａ
ｎｏｎｅｎｓｉｓ）、ダイズアブラムシ（Ａｐｈｉｓ
ｇｌｙｃｉｎｅｓ）、ニセダイコンアブラムシ（Ｌｉ
ｐａｐｈｉｓ ｐｓｅｕｄｏｂｒａｓｓｊｃａｅｅ）
、ダイコンアブラムシ（Ｂｒｅｖｉｃｏｒｙｎｅ ｂ
ｒａｓｓｉｃａｅ）、ワタアブラムシ（Ａｐｈｉｓ
ｇｏｓｓｙｐｉｉ）等の半翅目害虫、例えば／％スモン
ヨトウ（Ｓｐｏｄｏｐｔｅｒａ １ｉｔｕｒａ）、コ
ナガ（Ｐｌｕｔｅｌｌａ ｘｙｌｏｓｔｅｌｌａ）、
モンシロチョウ（Ｐｉｅｒｉｓｒａｐｅ ｃｒｕｃｉ
ｖｏｒａ）、ニカメイガ（Ｃｈｉｌ。More specifically, the compound (I) of the present invention and preparations containing the same can be used, for example, in the planthopper (Laodel
phax 5tiatelluss), Nephotettix cinctice
ps), Unaspis ya
nonensis), soybean aphid (Aphis
glycines), Japanese radish aphid (Li
paphis pseudobrassjcaee)
, radish aphid (Brevicoryne b)
rassicae), cotton aphid (Aphis
Hemiptera pests such as Spodoptera 1itura, Plutella xylostella,
Pierisrape cruci
vora), Chil.
５ｕｐｐｒｅｓｓａｌｉｓ）、タマナギンウワノ’（Ｐ
ｌｕｓｉａｎｉｇｒｉｓｉｇｎａ）、タバコガ（Ｅｅｌ
ｉｃｏｖｅｒｐａ ａｓｓｕｌｔａ）、アワヨトウ（
ｌｅｕｃａｎｉａ ５ｅｐａｒａｔａ）、ヨトウガ（
Ｍａｍｅｓｔｒａ ｂｒａｓｓｉｃａｅ）、コカクモ
ンノゝマキ（Ａｄｏｘｏｐｈｙｅｓ ｏｒａｎａ）、
ワタツメイガ（Ｓｙｌｌｅｐｔｅｄｅｒｏｇａｔａ）、
コブノメイガ（Ｃｎａｐｈａｌｏｃｒｏｃｉｓｍｅｄｉ
ｎａｌｉｓ）、ジャガイモガ（Ｐｈｔｈｏｒｉｍａｅａ
ｏｐｅｒｃｕｌｅｌｌａ）等の鱗翅目害虫、例えばニジ
ュウヤホシテントウムシ（Ｅｐｉｌａｃｈｎａ ｖｉ
ｇｉｎｔｉｏｃｔｏｐｕｎｃｔａｔａ）、ウリハムシ（
Ａｕｌａｃｏｐｈｏｒａ ｆｅｍｏｒａｌｉｓ）、キ
スジノミハムシ（Ｐｈｙｌｌｏｔｒｅｔａ ５ｔｒｉ
ｏｌａｔａ）、イネドロオイムシ（Ｏｕｌｅｍａ ｏ
ｒｇｚａｅ）、イネゾウムシ（Ｅｃｈｉｎｏｃｎｅｍｕ
ｓ ｓｑｕａｍｅｕｓ）等の鞘翅目害虫、例えばイエ
バエ（Ｍｕｓｃａ ｄｏｍｅｓｔｉｃａ）、アカイエ
カ（Ｃｕｌｅｘ ｐｉｐｉｅｎｓ ｐａｌｌｅｎｓ）
、ウシアブ（Ｔａｂａｎｕｓｔｒｉｇｏｎｕｓ）、タマ
ネギバエ（Ｈｙｌｅｍｙａ ａｎｔｉｑｕａ）、タネ
バエ（Ｈｙｌｅｍｙａ ｐｌａｔｕｒａ）等の双翅目
害虫、たとえばトノサマバッタ（Ｌｏｃｕｓｔａ ｍ
ｉｇｒａｔｏｒｉａ）、ケラ（Ｇｒｙｌｌｏｔａｌｐａ
ａｒｒｉｃａｎａ）等の直翅目害虫、たとえばチャ
バネゴキブリ（Ｂｌａｔｔｅｌｌａ ｇｅｒｍａｎｉ
ｃａ）、クロゴキブリ（Ｐｅｒｉｐｌａｎｅｔａ ｆ
ｕｌｉｇｉｎｏｓａ）等のゴキブリ目害虫、たとえばナ
ミハダニ（Ｔｅｔｒａｎｙｃｈｕｓ ｕｒｔｉｃａｅ
）、ミカンハダニ（Ｐａｎｏｎｙｃｈｕｓ ｃｉｔｒ
ｉ）、カンザワハダニ（Ｔｅｔｒａｎｙｃｈｕｓｋａｎ
ｚａｗａｉ）、ニセナミハダニ（Ｔｅｔｒａｎｙｃｈｕ
ｓｃｉｎｎａｂａｒｉｎｕｓ）、ワンゴハダニ（Ｐａｎ
ｏｎｙｃｈｕｓ ｕｌｍｉ）、ミカンサビタニ（Ａｃ
ｕｌｕｓ ｐｅｌｅｋａｓｓｉ）等のハタ二類、たと
えばイ不シンガレセンチュウ（Ａｐｈｅｌｅｎｃｈｏｉ
ｄｅｓ ｂｅｓｓｅｙｉ）等の線虫などの防除に特に
有効である。5uppressalis), Tamanagin Uwano' (P
lusianigrisigna), tobacco moth (Eel
icoverpa assulta), fall armyworm (
leucania 5eparata), armyworm moth (
Mamestra brassicae), Adoxophyes orana,
Sylleptederogata,
Cnaphalocrocismedi
nalis), potato moth (Phthorimaea)
Lepidopteran pests such as Epilachna vi
gintioctopunctata), cucumber beetle (
Aulacophora femoralis), Phyllotreta 5tri
olata), rice beetle (Oulema o
rgzae), rice weevil (Echinocnemu
Coleoptera pests such as Musca domestica, Culex pipiens pallens
Diptera pests such as Tabanustrigonus, Hylemya antiqua, and Hylemya platura, such as Locusta m.
igratoria), mole (Gryllotalpa)
Orthoptera pests such as the German cockroach (Blattella germani)
ca), Periplaneta f.
Cockroach pests such as Tetranychus uliginosa, Tetranychus urticae
), orange spider mite (Panonychus citr
i), Tetranychuskan
zawai), false red spider mite (Tetranychu)
scinnabarinus)
onychus ulmi), Citrus savitani (Ac
Aphelenchoi, such as Aphelenchoi
It is particularly effective in controlling nematodes such as P. des beseyi).
本発明化合物（Ｉ）またはその塩を殺虫殺ダニ剤として
使用するにあたっては、一般の農薬のとりうる形態、す
なわち、本発明化合物（Ｉ）またはその塩の１種又は２
種以上を使用目的によって適当な液体担体に溶解するか
、もしくは分散させるか、または適当な固体担体と混合
するか、もしくは吸着させる等、常法に従い乳剤、油剤
、噴霧剤、水和剤、粉剤、粒剤、錠剤、軟膏などの製剤
として使用するのが望ましい。さらにこれらの製剤には
必要に応じ、乳化剤、懸濁剤、展着剤、浸透剤、湿潤剤
、粘奨剤、安定剤などを添加してもよい。When using the compound (I) of the present invention or a salt thereof as an insecticide or acaricide, the compound (I) of the present invention or a salt thereof should be used in the form that can be taken by general agricultural chemicals, that is, one or two types of the compound (I) of the present invention or a salt thereof.
Emulsions, oils, sprays, wettable powders, and powders can be prepared using conventional methods such as dissolving or dispersing the seeds in a suitable liquid carrier, or mixing or adsorbing them with a suitable solid carrier, depending on the purpose of use. It is desirable to use it in the form of preparations such as granules, tablets, and ointments. Furthermore, emulsifiers, suspending agents, spreading agents, penetrating agents, wetting agents, viscous agents, stabilizers, etc. may be added to these preparations as necessary.
これらの製剤は自体公知の方法で調製することができる
。These formulations can be prepared by methods known per se.
殺虫殺ダニ剤中の本発明化合物（１）またはその塩の含
有割合は乳剤、水和剤などは１０〜９０重量％程度が適
当であり、油剤、粉剤などとして０１％〜１０重量％程
度か適当であり、粒剤としては１％〜２０重量％程度が
適当であるが、使用目的によっては、これらの濃度を適
宜変更してもよい。乳剤、水和剤などは使用に際して、
水などで適宜希釈増量（たとえば１００−１０００００
倍）して散布する。The appropriate content of the compound (1) of the present invention or its salt in insecticides and acaricides is about 10 to 90% by weight for emulsions, wettable powders, etc., and about 01% to 10% by weight for oils, powders, etc. The appropriate concentration for granules is about 1% to 20% by weight, but these concentrations may be changed as appropriate depending on the purpose of use. When using emulsions, hydrating agents, etc.
Dilute with water, increase volume (e.g. 100-100,000)
(double) and disperse.
使用する液体担体（溶媒）としては、例えば水、７ ／
Ｌ／ ：Ｉ−／Ｌ／類（たトエハ、メチルアルコール、
エチルアルコール、ｎ−プロピルアルコール、イソプロ
ピルアルコール、エチレングリコールナト）、エーテル
類（たとえば、ジオキサン、テトラヒドロフラン、エチ
レングリコールモノメチルエーテル、ジエチレングリコ
ールモノメチルエーテル、プロピレングリコールモノメ
チルエーテルナト）、ケトン類（たとえば、アセトン、
メチルエチルケトンなど）、脂肪族炭化水素類（たとえ
ば、ケロシン、灯油、燃料油、機械油など）、芳香族炭
化水素類（たとえば、ベンゼン、トルエン、キシレン、
ツルヘントナフサ、メチルナフタレンなど）、ハ０ゲン
化炭化水素（たとえば、メチレンクロリド、クロロポル
ム、四塩化炭素など）、酸アミド類（たとえば、ジメチ
ルホルムアミド、ジメチルアセトアミドなと）、エステ
ル類（たとえば、酢酸エチルエステル、酢酸ブチルエス
テル、脂肪酸グリセリンエステルなど）、ニトリル類（
例えば、アセトニトリル、プロピオニトリルなと）など
の溶媒が適当であり、これらは１種または２種以上を適
当な割合で混合して使用する。The liquid carrier (solvent) used is, for example, water, 7/
L/: I-/L/ (Tatoeha, methyl alcohol,
ethyl alcohol, n-propyl alcohol, isopropyl alcohol, ethylene glycol nat), ethers (e.g. dioxane, tetrahydrofuran, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether), ketones (e.g. acetone,
methyl ethyl ketone, etc.), aliphatic hydrocarbons (e.g., kerosene, kerosene, fuel oil, machine oil, etc.), aromatic hydrocarbons (e.g., benzene, toluene, xylene,
halogenated hydrocarbons (e.g., methylene chloride, chloroporm, carbon tetrachloride, etc.), acid amides (e.g., dimethylformamide, dimethylacetamide, etc.), esters (e.g., ethyl acetate) , butyl acetate, fatty acid glycerin ester, etc.), nitriles (
For example, solvents such as acetonitrile, propionitrile, etc. are suitable, and these solvents may be used alone or in combination of two or more in an appropriate ratio.
固体担体く希釈・増量剤）としては、植物性粉末（たと
えば、大豆粉、タバコ粉、小麦粉、木粉など）、鉱物性
粉末（たとえばカオリン、ベントナイト、酸性白土なと
のクレイ類、滑石粉、ロウ石粉なとのタルク類、珪藻土
、雲母粉などのシソ力類など）、アルミナ、硫黄粉末、
活性炭等がもちいられ、これらは１種又は２種以上を適
当な割合で混合して使用する。Examples of solid carriers (diluents and bulking agents) include vegetable powders (for example, soybean flour, tobacco flour, wheat flour, wood flour, etc.), mineral powders (for example, kaolin, bentonite, clays such as acid clay, talc powder, talc, diatomaceous earth, mica powder, etc.), alumina, sulfur powder,
Activated carbon and the like can be used, and these can be used alone or in a mixture of two or more in an appropriate ratio.
また、軟膏基剤としては、たとえばポリエチレングリコ
ール、ペクチン、たとえばモノステアリン酸グリセリン
エステル等の高級脂肪酸の多価アルコールエステル、た
とえばメチルセルローズ等のセルローズ誘導体、アルギ
ン酸すトリウム、ベントナイト、高級アルコール、たと
えばグリセリン等の多価アルコール、ワセリン、白色ワ
セリン、流動パラフィン、豚脂、各種植物油、ラノリン
、脱水ラノリン、硬化油、樹脂類等の１種または２種以
上、あるいはこれらに下記に示す各種界面活性剤を添加
したもの等を適宜使用することが出来る。Examples of ointment bases include polyethylene glycol, pectin, polyhydric alcohol esters of higher fatty acids such as glyceryl monostearate, cellulose derivatives such as methyl cellulose, storum alginate, bentonite, higher alcohols such as glycerin, etc. One or more of polyhydric alcohols, petrolatum, white petrolatum, liquid paraffin, lard, various vegetable oils, lanolin, dehydrated lanolin, hydrogenated oils, resins, etc., or the various surfactants shown below are added to these. You can use the ones that have been prepared as appropriate.
乳化剤、展着剤、浸透剤、分散剤などとして使用される
界面活性剤としては、必要に応じて石鹸類、ポリオキシ
エチレンアルキルアリールエーテル類（例、ノイゲン、
イー・ニー］、 ４．２（Ｅ −Ａ１４２）■、第−工
業製薬（株）製）、ポリオキシエチレンアリールエステ
ル類（Ｌノナール０、東邦化学（株）製）、アルキル硫
酸塩類（例、エマール１０■、エマール４０■、花王石
鹸（株）製）、アルキルスルホン酸塩類（例、不オゲン
０、ネオゲンＴＯ１第一工業製薬（株）製；ネオペレク
ス０花王石鹸（株）製）、ポリエチレングリコールエー
テルＭ（（Ｌ〕二ボール８５■、ノニポール１００■、
ノニポール１６０■、工注化成（株）製）、多価アルコ
ールエステル類（例、トウビーン２０■トウイーン８０
■、花王石鹸（株）製）などの非イオン系及びアニオン
系界面活性剤が用いられる。As surfactants used as emulsifiers, spreaders, penetrants, dispersants, etc., soaps, polyoxyethylene alkylaryl ethers (e.g., Neugen,
4.2 (E-A142)■, manufactured by Dai-Kogyo Seiyaku Co., Ltd.), polyoxyethylene aryl esters (L nonal 0, manufactured by Toho Chemical Co., Ltd.), alkyl sulfates (e.g. Emar 10■, Emar 40■, manufactured by Kao Soap Co., Ltd.), alkyl sulfonates (e.g., Inogen 0, Neogen TO1 manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.; Neoperex 0 manufactured by Kao Soap Co., Ltd.), polyethylene glycol Ether M ((L) 2 balls 85■, nonipole 100■,
Nonipole 160■, manufactured by Kochu Kasei Co., Ltd.), polyhydric alcohol esters (e.g., Tobean 20■Tween 80)
(2) Nonionic and anionic surfactants such as those manufactured by Kao Soap Co., Ltd. are used.
本発明化合物（１）またはその塩を農薬として使用する
にあたっては、化合物（Ｔ）またはその塩に更に他種の
殺虫剤（例えば、ピレスリン系殺虫剤、カルバメート系
殺虫剤、有機リン系殺虫剤、天然殺虫剤など）の他、殺
ダニ剤、殺線虫剤、除草剤、植物ホルモン剤、植物発育
調節物質、共力剤、誘引剤、忌避剤、色素、肥料などと
適宜の割合で混合し、使用することもできる。When using the compound (1) of the present invention or a salt thereof as a pesticide, compound (T) or a salt thereof may be combined with other types of insecticides (for example, pyrethrin insecticides, carbamate insecticides, organophosphorus insecticides, (natural insecticides, etc.), acaricides, nematicides, herbicides, plant hormones, plant growth regulators, synergists, attractants, repellents, pigments, fertilizers, etc. in appropriate proportions. , can also be used.
本発明化合物（１）またはその塩を含有する製剤のうち
乳剤及び水和剤は通常、本発明化合物（Ｉ）の濃度とし
て通常約２０〜５０００ ｐｐｍ、好ましくは５０〜１
０００ ｐｐｍ程度になるように希釈して使用するのが
好ましい。Among the preparations containing the compound (1) of the present invention or a salt thereof, emulsions and wettable powders usually have a concentration of the compound (I) of the present invention of about 20 to 5000 ppm, preferably 50 to 1
It is preferable to use it after diluting it to about 000 ppm.
本発明化合物（Ｉ）またはその塩を農業用殺虫剤として
用いる場合、その使用量は化合物（Ｉ）に換算して１０
アール当り約１０ｇ〜ＩＫｇ、好ましくは約３０ｇ〜５
００ｇが適当である。本発明化合物（１）を含有する製
剤は公知の方法により植物に処理することができ、例え
ば葉茎に直接散布するか植物の根元に処理する。When the compound (I) of the present invention or a salt thereof is used as an agricultural insecticide, the amount used is 10
About 10g to IKg per are, preferably about 30g to 5
00g is appropriate. A preparation containing the compound (1) of the present invention can be applied to plants by a known method, for example, by spraying it directly onto the leaves and stems or applying it to the base of the plant.
噴霧剤は適当な噴霧器を利用して、そのままで噴霧して
もよいが、例えばフロン、液化石油ガス、ジメチルエー
テル、炭酸ガス等の噴射剤を加えていわゆる殺虫エアゾ
ールにすることもできる。The spray may be sprayed as is using a suitable sprayer, but it may also be made into a so-called insecticidal aerosol by adding a propellant such as fluorocarbons, liquefied petroleum gas, dimethyl ether, or carbon dioxide gas.
発明の効果
本発明化合物（Ｉ）またはその塩は、野菜（例えば、キ
ャベ・ハハクサイ、キュウリ、ジャガイモ等）、果樹（
例えば、みかん、なし等）、花き（例えば、バラ、菊等
）、タバコ等の諸害虫（例えば、ヨトウムシ、アオムシ
、コナガ、アブラムシ類、テントウムシタマシ幼虫、ジ
ャガイモガ、コカクモンハマキ、ヤノネカイガラムシ、
ツノロウムシ、ハマキム／、タバコアオムシ等）の防除
に有効てある。Effects of the Invention The compound (I) of the present invention or its salt can be used in vegetables (for example, cabbage, Chinese cabbage, cucumber, potato, etc.), fruit trees (
(e.g., tangerines, pears, etc.), flowers (e.g., roses, chrysanthemums, etc.), various pests such as tobacco (e.g., armyworm, green caterpillar, mealybug, aphids, ladybug larvae, potato moth, blackberry leafhopper, green scale insect,
It is effective in controlling hornworms, hamachim, tobacco caterpillars, etc.).
加えて、本発明化合物は、植物に対する薬害や人畜毒性
、魚毒性が低いという効果も有する。In addition, the compound of the present invention also has the effect of having low phytotoxicity to plants, toxicity to humans and animals, and toxicity to fish.
火塵珂
次に実施例によって本発明をさらに詳しく説明するが、
本発明はこれらの実施例に限定されるべきものではない
。Next, the present invention will be explained in more detail with reference to Examples.
The invention should not be limited to these examples.
尚、以下の実施例におけるＮＭＲデータは、それぞれδ
値をｐｐｍで示した。各略号は次の意義を有する。In addition, the NMR data in the following examples are δ
Values are expressed in ppm. Each abbreviation has the following meaning.
Ｓ：シングレット、ｄ：ダブレット、ｍ：マルチブレッ
ト、ｂ・ブロード、Ｊ・カップリング定数、Ｎ２．ヘル
ツ、ＣＤ、、ＯＤ：重メチルアルコール、Ｍｅ：メチル
基、Ｅｔ：エチル基、”Ｐｒ：ｎ−プロピル基、’Ｂｕ
：ｉ−ブチル基、ｔＢｕ：ｔ−ブチル基実施例１
３．３′−ジチオビス（２−ジメチルアミノプロパン−
Ｉ−スルフィニックアシッド） （化合物Ｎｏ。S: singlet, d: doublet, m: multiplet, b broad, J coupling constant, N2. Hertz, CD, OD: heavy methyl alcohol, Me: methyl group, Et: ethyl group, "Pr: n-propyl group, 'Bu
: i-butyl group, tBu: t-butyl group Example 1 3.3'-dithiobis(2-dimethylaminopropane-
I-sulfinic acid) (Compound No.
１とする）の合成
＝２０
４−ジメチルアミノ−１２−ジチオラン １１−ジオキ
サイド３．６３ｇ（０，０２ｍｏｌ）をメタノール５０
Ｍ１に加え、室温でよく撹拌しながら、チオフェノール
２．２ｇ（０，０２ｍｏｌ）を滴下した。室温で３時間
反応した後、エーテル１００１ｎｌを加え析出した結晶
を濾取した。ｍ、ｐ、１４７−８°Ｃの白色粉末品とし
て３，３′−ジチオビス（２−ジメチルアミンプロパン
−１−スルフィニックアシッド）を３．５ｇ（９５，９
％）得た。Synthesis of 1)=20 3.63 g (0.02 mol) of 4-dimethylamino-12-dithiolane 11-dioxide was dissolved in methanol 50
In addition to M1, 2.2 g (0.02 mol) of thiophenol was added dropwise while stirring well at room temperature. After reacting at room temperature for 3 hours, 1001 nl of ether was added and the precipitated crystals were collected by filtration. m, p, 3.5 g (95,9
%)Obtained.
元素分析値 Ｃ，、Ｎ２．Ｎ２０．Ｓ。Elemental analysis value C,, N2. N20. S.
実測値： Ｃ：３１．０６． Ｈ：６．７８．
Ｎ ：６．８４計算値： Ｃ：３０．６７、 Ｈ：
６．９５ Ｎニア、１５ＳＩ−ＭＳ（シムス マスス
ペクトル）ｍ／ｚ３６．５（Ｍ”＋１）
ＮＭＲ（ＣＤｓＯＤ）： ２．７２（４Ｈ，ｄ、Ｊ＝６
．３Ｈｚ）、 ２．９１（１２Ｈ，ｓ）、 ３．３５
と３．５２（４Ｈ，ｍ）、 ４．３２（２Ｈ，ｍ）。Actual value: C: 31.06. H:6.78.
N: 6.84 Calculated value: C: 30.67, H:
6.95 N Near, 15SI-MS (Sims Mass Spectrum) m/z 36.5 (M”+1) NMR (CDsOD): 2.72 (4H, d, J=6
．． 3Hz), 2.91 (12H, s), 3.35
and 3.52 (4H, m), 4.32 (2H, m).
貫３ＣＮＭＲ（Ｄ ２０）： ３７．７． ３８．０
（Ｃ１，Ｓ）、 ４２．１７４２．２４（ＮＭｅ）、
５７．８．５８．１（ＣＩ１２ＳＯ，ＩＩ）、 ６２
．８．６３゜２（ＮＣＲ）。3CNMR (D 20): 37.7. 38.0
(C1,S), 42.1742.24 (NMe),
57.8.58.1 (CI12SO, II), 62
．． 8.63°2 (NCR).
実施例２
３．３′−ジチオビス（２−ジメチルアミノプロパン−
１−スルフィニックアシッド）ナトリウム塩（化合物Ｎ
ｏ、 ２とする）の合成
４−ジメチルアミノ−１，２−ジチオラン １゜１−ジ
オキサイド３．６３ｇ（０，０２ｍｏｌ）をメタノール
５０滅に加え、室温でよく撹拌しながら、チオフェノー
ルのナトリウム塩２．６４ｇ（０，０２ｍｏｌ）を加え
た。加え終ってから室温で１時間、４０℃で３時間反応
した。反応終了後室温まで冷却し、エーテル５０滅を加
え、析出した結晶をろ取した。ｍ、ｐ、２５０°Ｃ以上
の白色粉末品として標記の化合物（Ｎｏ、２）を３．４
８ｇ（８５％）得た。Example 2 3.3'-dithiobis(2-dimethylaminopropane-
1-sulfinic acid) sodium salt (compound N
Synthesis of 4-dimethylamino-1,2-dithiolane 1゜1-dioxide (3.63 g (0.02 mol)) was added to 50 ml of methanol, and while stirring well at room temperature, the sodium thiophenol was added. 2.64 g (0.02 mol) of salt was added. After the addition was completed, the reaction was carried out at room temperature for 1 hour and at 40°C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, 50% of ether was added, and the precipitated crystals were collected by filtration. m, p, 3.4% of the title compound (No. 2) as a white powder product with a temperature of 250°C or higher
8g (85%) obtained.
Ｎ Ｍ Ｒ（ＣＤ ３０ Ｄ ）： ２．２９（１２Ｈ
，ｓ）、 ２．２〜２．６５（４Ｈ。NMR(CD30D): 2.29(12H
, s), 2.2-2.65 (4H.
ｍ）、 ２．９〜３．１５（４１１，ｍ）、 ３．２〜
３．４（２＋１． ｍ）。m), 2.9~3.15 (411, m), 3.2~
3.4 (2+1.m).
実施例３
２−ジメチルアミノ−３−（イソプロビルジスルファニ
ル）プロパン−１−スルフィニックアシッド（化合物Ｎ
ｏ、 ３とする）の合成
４−ジメチルアミノ−１２−ジチオラン １゜１−ジオ
キサイド１．８１ｇ（０，０１ｍｏｌ）をメタノール２
０滅に加え、室温でよく撹拌しながら、イソプロピルメ
ルカプタン２．２ｇ（０，０１ｍｏｌ）を滴下した。室
温で２時間反応した後、溶媒を減圧下に除去しエーテル
１００蔵を加え析出した結晶を濾取した。ｍ、ｐ、１３
５−６°Ｃの白色粉末品として２−ジメチルアミノ−３
−（イソプロビルジスルファニル）プロパン−１−スル
フィニックアシッドを２．４ｇ（９３，３％）を得た。Example 3 2-dimethylamino-3-(isopropyldisulfanyl)propane-1-sulfinic acid (compound N
Synthesis of 4-dimethylamino-12-dithiolane 1゜1-dioxide (1.81 g (0.01 mol)) in methanol 2
In addition, 2.2 g (0.01 mol) of isopropyl mercaptan was added dropwise to the mixture while stirring well at room temperature. After reacting at room temperature for 2 hours, the solvent was removed under reduced pressure, 100 g of ether was added, and the precipitated crystals were collected by filtration. m, p, 13
2-dimethylamino-3 as a white powder at 5-6°C
2.4 g (93.3%) of -(isopropyldisulfanyl)propane-1-sulfinic acid was obtained.
元素分析値 Ｃｅ ＨＩｅ Ｎ Ｏｔ Ｓ ３；実測値
： Ｃ：３７Ｊ２． Ｈニア、４４ Ｎ：５．２
計算値・ Ｃ：３７．４１． Ｈニア、 ４８．
Ｎ ：５．４１Ｎ Ｍ Ｒ（ＣＤ ３０ Ｄ ）： １
．３１（６Ｈ１ｄ、Ｊ＝ ６．３Ｈｚ）、２．４２、７
（２）１． ｍ）、 ２．８０（６１（、ｓ）、 ２．
８０−３．１（２Ｈ，ｍ）。Elemental analysis value Ce HIe N Ot S 3; Actual value: C: 37J2. H near, 44 N: 5.2
Calculated value・C: 37.41. H Near, 48.
N: 5.41NMR(CD30D): 1
．． 31 (6H1d, J=6.3Hz), 2.42, 7
(2)1. m), 2.80(61(,s), 2.
80-3.1 (2H, m).
３、０５−３．３（ＩＨ，ｍ）、 ４．４−４．６５（
＋、Ｈ，ｍ）実施例４
２−ジメチルアミノ−３−（イソブチルジスルファニル
）プロパン−１−スルフィニックアシッド（化合物Ｎｏ
、 ４とする）の合成
実施例３と同様にして標記化合物を得た。3, 05-3.3 (IH, m), 4.4-4.65 (
+, H, m) Example 4 2-dimethylamino-3-(isobutyldisulfanyl)propane-1-sulfinic acid (compound No.
, 4) The title compound was obtained in the same manner as in Synthesis Example 3.
ｍ、ｐ、１２７−８°Ｃ１収率９５．３％。m, p, 127-8°C1 yield 95.3%.
ＮＭＲ（ＣＤ３０Ｄ）： １．０（６Ｈ１ｄ、Ｊ＝６
Ｈｚ）、１．７５ ２゜１５（ＩＨ，ｍ）、 ２．４
５−２．６５（２ｔ（、ｍ）、 ２．７２（２Ｈ，ｄ
、 Ｊ＝ ６Ｈｚ）、 ２．７９（６Ｈ，ｓ）、
２．８５と３．１０（２）１． ｍ）、４．３−４゜６
５（ｌｔＬ ｍ）、 １２．４（ＩＨ，ｂｓ）。NMR (CD30D): 1.0 (6H1d, J=6
Hz), 1.75 2°15 (IH, m), 2.4
5-2.65(2t(,m), 2.72(2H,d
, J=6Hz), 2.79(6H,s),
2.85 and 3.10 (2) 1. m), 4.3-4゜6
5 (ltL m), 12.4 (IH, bs).
実施例５
２−ジメチルアミノ−３−（アリルジスルファニル）プ
ロパン−１−スルフィニックアシッド（化合物Ｎｏ、
５とする）の合成
実施例３と同様にして標記化合物を得た。Example 5 2-dimethylamino-3-(allyldisulfanyl)propane-1-sulfinic acid (compound No.
5) The title compound was obtained in the same manner as in Synthesis Example 3.
ｍ、ｐ、９Ｂ−９°Ｃ１収率７８．３％ＮＭＲ（ＣＤ３
０Ｄ）： ２．６−２．８（２Ｈ，ｍ）、 ２．９（６
Ｈ，ｓ）。m, p, 9B-9°C1 yield 78.3% NMR (CD3
0D): 2.6-2.8 (2H, m), 2.9 (6
H,s).
３．７−３．４（２Ｈ，ｍ）、 ３．４５（２Ｈ，ｄ、
Ｊ＝６．５Ｈｚ）、 ４．１５４．４５（ｉｌｌ、 ｍ
）、 ５．１−５．４５（２Ｈ，ｍ）、 ５．７−６．
１（ＩＨ。3.7-3.4 (2H, m), 3.45 (2H, d,
J=6.5Hz), 4.154.45(ill, m
), 5.1-5.45 (2H, m), 5.7-6.
1 (IH.
ｍ）、’ １２．１（ＩＨ，ｂｓ）。m), '12.1 (IH, bs).
実施例６
２−ジメチルアミノ−３−（ｐ−１−プチルベンジルジ
スルファニル）フロパン−１−スルフィニックアシッド
（化合物Ｎ０８６とする）の合成実施例３と同様にして
標記化合物を得た。Example 6 Synthesis of 2-dimethylamino-3-(p-1-butylbenzyldisulfanyl)furopane-1-sulfinic acid (referred to as compound N086) The title compound was obtained in the same manner as in Example 3.
ｍ、ｐ、 １３ ］−２°Ｃ２収率９６．２％ＮＭＲ（
ＣＤ３０Ｄ）： １．２９（６Ｈ，Ｓ）＋２．０ ２．
４５（４ＨＩｍ）、 ２．５１（６Ｌｓ）、 ３．８
２（２１（、ｓ）、 ４．１−４．５（ＩＨ，＋＋＋）
。m, p, 13]-2°C2 yield 96.2% NMR (
CD30D): 1.29(6H,S)+2.0 2.
45 (4HIm), 2.51 (6Ls), 3.8
2 (21 (, s), 4.1-4.5 (IH, +++)
.
１２、１（ＩＨ，ｂｓ）。12, 1 (IH, bs).
実施例７
２−ジメチルアミノ−３−（トリフルオロアセチルベン
ゾイルメチル）チオプロパン−１−スルフィニックアシ
ッド（化合物ＮＯ６７とする）の合成ネレイストキシン
ジオキサイド０．５ｇ（０，００２８ｍｏｌ）、４，
４．４−１リフルオロ−１−フェニル−１，３−ブタン
ジオンｇ（ｍｏｌ）をメタノール１０成に加え、よく撹
拌しながら加熱還流下で８時間反応した。溶媒を減圧下
に除去し、残渣をシリカゲルカラムクロマトグラフィー
（ＣＨＣρ３／ＭｅＯＨ＝ｌ Ｏ／１）で精製し油状物
として標記化合物を０．８ｇ（７３％）を得た。Example 7 Synthesis of 2-dimethylamino-3-(trifluoroacetylbenzoylmethyl)thiopropane-1-sulfinic acid (referred to as compound NO67) Nereistoxin dioxide 0.5 g (0,0028 mol), 4,
4.4-1 g (mol) of 1-lifluoro-1-phenyl-1,3-butanedione was added to 10 methanol and reacted for 8 hours under heating and reflux with thorough stirring. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (CHCρ3/MeOH=1 O/1) to yield 0.8 g (73%) of the title compound as an oil.
ＮＭＲ（ＣＤＣ（＋３）： ２．８（６８，Ｓ）、 ２
．４ ２．８（２Ｈ，ｍ）。NMR(CDC(+3): 2.8(68,S), 2
．． 4 2.8 (2H, m).
３．４５（ＩＨ，ｓ）、 ３．９（２）！、ｄ、Ｊ＝４
．５Ｈｚ）、 ４．２−４．６（ＩＬｍ）、 ７．１（
ＬＨ，ｂｓ）、 ７．４−７．７ ａｎｄ ７．９−８
．１（５Ｈｍ）。3.45 (IH, s), 3.9 (2)! , d, J=4
．． 5Hz), 4.2-4.6(ILm), 7.1(
LH, bs), 7.4-7.7 and 7.9-8
．． 1 (5Hm).
実施例８
２−ジメチルアミノ−３−（１−ニトロインダンジオン
−１−）チオプロパン−１−スルフィニックアシッド（
化合物Ｎ０９８とする）の合成ネレイストキシン ジオ
キサイド１．８１ｇ（００１ｍｏｌ）、Ｉ−二トロイン
ダンジオン２．２ｇ（０゜０１ｍｏｌ）をメタノール２
０滅に加え、室温で３０分反応した。反応終了５°Ｃま
で冷却し析出した結晶を濾取した。ｍ、ｐ、１３３−４
°Ｃ（ｄｅｃ、 ）の淡黄色結晶２．４ｇ（８２，５２
％）を得た。Example 8 2-dimethylamino-3-(1-nitroindanedione-1-)thiopropane-1-sulfinic acid (
Synthesis of compound N098) 1.81 g (001 mol) of nerei toxin dioxide and 2.2 g (001 mol) of I-nitroindandione were mixed with methanol 2
In addition, the reaction was continued at room temperature for 30 minutes. After the reaction was completed, the mixture was cooled to 5°C, and the precipitated crystals were collected by filtration. m, p, 133-4
2.4 g (82,52
%) was obtained.
元素分析値： ＣｏＨ，８ＮＯ２Ｓ３；実測値：
Ｃ：３７．３２． Ｈニア、４４． Ｎ：５．２計
算値 Ｃ：３７．４Ｌ Ｈニア、１１８． Ｎ：５
．４１ＮＭＲ（ＤＭＳ〇−ｄ。）： ２．９８（６８，
ｓ）、 ３．９８−４．３５（４Ｈ，ｍ）、 ４．４−
４．８（ｉｌｌ、ｍ）、 ７．５８（５Ｈ，ｍ）」二記
実施例１〜８で得た化合物（１）の代表例である上記化
合物Ｎｏ、 ］〜８を融点又は沸点及び収率と共に下記
の表−１にまとめた。Elemental analysis value: CoH, 8NO2S3; Actual value:
C:37.32. H Near, 44. N: 5.2 calculated value C: 37.4L H near, 118. N:5
．． 41NMR (DMS〇-d.): 2.98 (68,
s), 3.98-4.35 (4H, m), 4.4-
4.8 (ill, m), 7.58 (5H, m)'' Compounds No. 2 to 8, which are representative examples of compounds (1) obtained in Examples 1 to 8, were evaluated for melting point or boiling point and yield. The percentages are summarized in Table 1 below.
表−１
以下の製剤例及び試験例における化合物Ｎｏ、は表−１
の化合物Ｎｏ、を意味する。もちろん本発明目的物はこ
れらのみに限定されるものではない。Table-1 Compound numbers in the following formulation examples and test examples are shown in Table-1
It means compound No. Of course, the objects of the present invention are not limited to these.
製剤例１
化合物Ｎｏ、 ５ ２０重量％キ
シレン ７５重量％ポリオキシ
エチレングリコールエーテル（ノニポール８５ｏ）
５重量％以」二の成分を混合して乳剤を
製造した。Formulation Example 1 Compound No. 5 20% by weight xylene 75% by weight polyoxyethylene glycol ether (Nonipol 85o)
An emulsion was prepared by mixing at least 5% by weight of the two components.
製剤例２
化合物Ｎｏ、 ８ ３０重量％リ
グニンスルホン酸ナトリウム ５重量％ポリオキシ
エチレングリコールエーテル（ノニポール８５０）
５重量％ホワイトカーボン
３０重量％クレイ
３０重量％以上の成分を混合して水和剤を製造した。Formulation Example 2 Compound No. 8 30% by weight sodium lignin sulfonate 5% by weight polyoxyethylene glycol ether (Nonipol 850)
5% by weight white carbon
30% by weight clay
A wettable powder was prepared by mixing 30% by weight or more of the components.
製剤例３
化合物Ｎｏ、６ 、 ３重量％ホ
ワイトカーホン ３重量％クレイ
９４重量％以」二の成分を
混合して粉剤を製造した。Formulation example 3 Compound No. 6, 3% by weight white carbon 3% by weight clay
A powder was prepared by mixing 94% by weight or more of the two components.
製剤例４
化合物Ｎｏ、 ５ １０重量％
リグニンスルホン酸ナトリウム ５重量％クレイ
８５重量％以上の成分を
混合して造粒して粒剤を得た。Formulation Example 4 Compound No. 5 10% by weight
Sodium ligninsulfonate 5% by weight clay
Granules were obtained by mixing and granulating 85% by weight or more of the components.
試験例１
トビイロウンカ（Ｎｉｒａｐａｒｖａｔａ ｌｕｇｅ
ｎｓ）に対する効果
供試化合物を製剤例１の処方に従って乳剤とし、水で希
釈し、５ Ｑ Ｏｐｐｍの処理液を調製した。この処理
液をスプレーガンで１１０ｄ／ペーパーポツトを散布し
た。試験管の底に水を入れ、ここに処理イネ苗を入れた
後、トビイロウンカ３令幼虫１０頭を放ち、アルミ栓を
した。Test Example 1 Niraparvata luge
The test compound was made into an emulsion according to the formulation of Formulation Example 1, and diluted with water to prepare a treatment solution of 5 Q Oppm. This treatment solution was sprayed onto a 110 d/paper pot using a spray gun. After pouring water into the bottom of a test tube and placing the treated rice seedlings there, 10 3rd instar brown planthopper larvae were released and the tube was capped with an aluminum stopper.
試験管を室内（２５°Ｃ）に２４時間置き、死亡虫数を
調べた。試験は２反復で行い、代表化合物の死亡率（２
回の平均）で表わし表−２に示した。The test tube was placed indoors (25°C) for 24 hours, and the number of dead insects was determined. The test was repeated twice, and the mortality rate of the representative compound (2
The results are shown in Table 2.
試験例２
ハスモンヨトウに対する効果
供試化合物として化合物Ｎ０１３を製剤例１の処方に従
って乳剤とし、水で希釈し、５００ ｐｐｍの処理液を
調製した。この処理液をスプレーガンを用いて２Ｏｔｒ
＆／ボットで散布した。処理液が乾いた後、クイズの単
葉２枚を切り取り、アイスクリーム力、プに収め、ハス
モンヨトウの３令幼虫１０頭を放ぢ、放出後カップを室
内（２５°Ｃ）に置き、２日後の死亡虫を数えた。化合
物Ｎｏ、 ３の死亡率（２回の平均）は８０％であった
。Test Example 2 Compound N013 was made into an emulsion as a test compound for effectiveness against Spodoptera japonica according to the formulation of Formulation Example 1, and diluted with water to prepare a 500 ppm treatment solution. Apply this treatment solution to 2 Otr using a spray gun.
&/Distributed by bot. After the treatment solution had dried, cut two single leaves of Quiz, put them in an ice cream cup, and release 10 3rd instar larvae of Spodoptera larvae. We counted dead insects. The mortality rate (average of two tests) of compound No. 3 was 80%.
試験例３
ナミハダニ（Ｔｅｔｒａｎｙｃｈｕｓ ｕｒｔｉｃａ
ｅ）に対する効供試化合物を製剤例１の処方で乳剤とし
、水を展着剤ダイン■が３０００倍希釈になるよう添加
し、５００ｐｐｍの水溶液を調製した。アイスクリーム
カップで水耕したインゲンの実生苗にナミハダニの雌成
虫１０頭を接種し、２４時間ガラス室（２８℃）に置き
、水溶液２０滅をインゲンに散布した。散布後カップを
ガラス室内に戻し、散布後２日目に葉上に生息している
幼成虫数を調べた。Test Example 3 Two-spotted spider mite (Tetranychus urtica)
Efficacy against e) The test compound was made into an emulsion according to the formulation of Formulation Example 1, and water was added to dilute the spreading agent Dyne 1 by 3000 times to prepare a 500 ppm aqueous solution. Ten female adult red spider mites were inoculated into green bean seedlings grown hydroponic in an ice cream cup, placed in a glass room (28°C) for 24 hours, and an aqueous solution of 20% was sprayed on the green beans. After spraying, the cup was returned to the glass chamber, and on the second day after spraying, the number of young adults living on the leaves was determined.
試験は２反復で行い、試験結果は減少率（２回の平均）
を下記の式によって求めた。The test was conducted in 2 repetitions, and the test results are the reduction rate (average of 2 repetitions)
was calculated using the following formula.
化合物Ｎ０１５及びＮｏ、 ７の減少率は、それぞれ５
０％及び５０％であった。The reduction rate of compounds N015 and No. 7 was 5, respectively.
They were 0% and 50%.
上記の試験結果から本発明化合物が、各種害虫に対して
優れた殺虫殺ダニ作用を奏することがわかる。とりわけ
、ウンカに対する防除効果が顕著であることも示された
。The above test results show that the compounds of the present invention exhibit excellent insecticidal and acaricidal effects against various pests. In particular, it was also shown that the control effect against planthoppers was remarkable.
Claims (3)
基を有していてもよい炭化水素残基を示すか、あるいは
Ｒ＾１とＲ＾２が一緒になって隣接する窒素原子ととも
に環を形成していてもよく、Ｒ＾３は電子吸引性基を有
するアルキル基、又は式Ｒ＾４Ｓ−（式中、Ｒ＾４は置
換基を有していてもよい炭化水素残基を示す。）で表わ
される基を示す。］で表わされるスルフィン酸誘導体又
はその塩。(1) Formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 and R^2 each represent a hydrogen atom or a hydrocarbon residue that may have a substituent, or R^ 1 and R^2 may be taken together to form a ring with the adjacent nitrogen atom, and R^3 is an alkyl group having an electron-withdrawing group, or has the formula R^4S- (where R^4 represents a hydrocarbon residue which may have a substituent. ] A sulfinic acid derivative or a salt thereof.
される化合物又はその塩を反応させることを特徴とする
請求項１に記載のスルフィン酸誘導体又はその塩の製造
法。(2) Formula▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R^1 and R^2 are as defined in claim 1. ] or a salt thereof, and a compound represented by the formula R^3H [wherein R^3 is as defined in claim 1]. 2. The method for producing a sulfinic acid derivative or a salt thereof according to claim 1, which comprises reacting a compound represented by: or a salt thereof.
含有することを特徴とする殺虫殺ダニ組成物。(3) An insecticidal and acaricidal composition comprising the sulfinic acid derivative or its salt according to claim 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29438088 | 1988-11-21 | ||
| JP63-294380 | 1988-11-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02223549A true JPH02223549A (en) | 1990-09-05 |
Family
ID=17806973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1023789A Pending JPH02223549A (en) | 1988-11-21 | 1989-01-18 | Sulfinic acid derivative, production thereof and composition thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02223549A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5679845A (en) * | 1995-04-21 | 1997-10-21 | Sogo Pharmaceutical Company Limited | Process for producing taurine analogues |
| US5856563A (en) * | 1996-08-14 | 1999-01-05 | Sugo Pharmaceutical Company Limited | Process and producing taurine analogues |
-
1989
- 1989-01-18 JP JP1023789A patent/JPH02223549A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5679845A (en) * | 1995-04-21 | 1997-10-21 | Sogo Pharmaceutical Company Limited | Process for producing taurine analogues |
| US5856563A (en) * | 1996-08-14 | 1999-01-05 | Sugo Pharmaceutical Company Limited | Process and producing taurine analogues |
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