JPH06776B2 - Hexahydrotriazine compound, its production method and insecticide - Google Patents
Hexahydrotriazine compound, its production method and insecticideInfo
- Publication number
- JPH06776B2 JPH06776B2 JP2024199A JP2419990A JPH06776B2 JP H06776 B2 JPH06776 B2 JP H06776B2 JP 2024199 A JP2024199 A JP 2024199A JP 2419990 A JP2419990 A JP 2419990A JP H06776 B2 JPH06776 B2 JP H06776B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- alkyl group
- lower alkyl
- general formula
- 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.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明は新規ヘキサヒドロトリアジン化合物、該化合物
の製造法および該化合物を活性成分として含有する殺虫
剤に関する。TECHNICAL FIELD The present invention relates to a novel hexahydrotriazine compound, a process for producing the compound and an insecticide containing the compound as an active ingredient.
従来の技術 従来、有害生物の防除剤として、各種薬剤が開発され殺
虫剤として利用されている。とくに有機リン剤、カーバ
メイト剤、近年では、合成ピレスロイド剤が主たるもの
である。これら殺虫剤を連用することによって、各種害
虫に対して抵抗性が発達し、それらの防除が困難となっ
てきている。また一方従来の殺虫剤のあるものは、高い
殺虫力を有していても温血動物に対する毒性、魚類、甲
殻類に対する毒性が高かったり、あるいは残留が多すぎ
て生態系を乱すなどの環境汚染が問題になっている。従
って従来の殺虫剤に対して、抵抗性を獲得した害虫に
も、また感受性の高い害虫にも優れた防除効果を有し、
温血動物に対する毒性、魚類、甲殻類などに対する毒性
が低く、また残留が少なく、植物に対する安全性も高い
新規な殺虫剤の開発が望まれている。2. Description of the Related Art Conventionally, various chemicals have been developed and used as insecticides as pest control agents. In particular, organic phosphorus agents, carbamate agents, and in recent years, synthetic pyrethroid agents are the main ones. By continuously using these insecticides, resistance to various pests has been developed and it has become difficult to control them. On the other hand, some conventional insecticides are highly toxic to warm-blooded animals, highly toxic to fish and crustaceans even if they have high insecticidal activity, or have too much residue to disturb the ecosystem such as disturbing the ecosystem. Is a problem. Therefore, against conventional pesticides, even pests that have acquired resistance, also have an excellent control effect against highly sensitive pests,
It is desired to develop a new insecticide having low toxicity to warm-blooded animals, low toxicity to fish and crustaceans, low residue, and high safety to plants.
発明が解決しようとする課題 本発明の目的は、従来の殺虫剤に対して抵抗性を獲得し
た害虫にも優れた防除効果を有し、温血動物や魚類、甲
殻類などに対する毒性が低く、また残留が少なく、植物
に対する安全性も高い、従来の殺虫剤よりも一層改良さ
れた殺虫剤を提供することにある。Problems to be Solved by the Invention The object of the present invention is to have an excellent control effect on pests that have acquired resistance to conventional insecticides, and have low toxicity to warm-blooded animals, fish, crustaceans, etc., Another object of the present invention is to provide an insecticide which has less residue and is highly safe to plants, and which is further improved than conventional insecticides.
課題を解決するための手段 本発明者らは新規ヘキサヒドロトリアジン化合物につい
て種々検討の結果、一般式〔Ｉ〕 （式中Ｒは低級アルキル基または低級アルケニル基を示
し、Ｒ1は低級アルキル基、低級アルケニル基または低
級アルキニル基を示し、 Ｒ2は または で表される基を示す） で表されるヘキサヒドロトリアジン化合物が極めて協力
で速効的な殺虫剤となる得ることを見出して本発明を完
成するに至った。Means for Solving the Problems As a result of various investigations on the novel hexahydrotriazine compound, the present inventors have found that the compound of the general formula [I] (In the formula, R represents a lower alkyl group or a lower alkenyl group, R 1 represents a lower alkyl group, a lower alkenyl group or a lower alkynyl group, and R 2 represents Or The present invention has been completed by discovering that a hexahydrotriazine compound represented by the formula (4) can be a fast-acting insecticide with great cooperation.
上記の一般式〔Ｉ〕で表される本発明化合物は下記の方
法によって製造することができる。The compound of the present invention represented by the above general formula [I] can be produced by the following method.
（式中Ｒは低級アルキル基または低級アルケニル基を示
し、Ｒ1は低級アルキル基、低級アルケニル基または低
級アルキニル基を示し、 Ｒ2は または で表される基を示し、Ｘはハロゲン原子を示す） 本製造法(a)においては、上記反応式に示されるとおり
一般式〔II〕で表される化合物と、一般式〔III〕で表
される例えばビス（クロロメチル）メチルアミン、ビス
（クロロメチル）エチルアミン、ビス（クロロメチル）
プロピルアミンとを溶媒中で塩基性物質の存在下に反応
させることによって本発明化合物を容易に得ることがで
きる。溶媒としてはエーテル、テトラヒドロフラン等の
エーテル類、アセトニトリル、芳香族炭化水素、塩素化
炭化水素、ＤＭＦ，ＤＭＳＯ等を単独または混合して使
用することができる。塩基性物質としては、例えば水酸
化ナトリウム、炭酸カリウム等の無機塩基ならびにピリ
ジン、トリエチルアミン等の有機塩基が使用でき、通常
過剰量が使用されるが、好ましくは2.1〜４倍モルが適
当である。反応温度は−２０℃から１００℃まで任意に
設定できるが好ましくは−５〜１０℃が適当である。 (In the formula, R represents a lower alkyl group or a lower alkenyl group, R 1 represents a lower alkyl group, a lower alkenyl group or a lower alkynyl group, and R 2 represents Or In the present production method (a), a compound represented by the general formula [II] and a compound represented by the general formula [III] are represented by the above reaction formula. For example, bis (chloromethyl) methylamine, bis (chloromethyl) ethylamine, bis (chloromethyl)
The compound of the present invention can be easily obtained by reacting propylamine in a solvent in the presence of a basic substance. As the solvent, ethers, ethers such as tetrahydrofuran, acetonitrile, aromatic hydrocarbons, chlorinated hydrocarbons, DMF, DMSO and the like can be used alone or in combination. As the basic substance, for example, inorganic bases such as sodium hydroxide and potassium carbonate, and organic bases such as pyridine and triethylamine can be used. Usually, an excess amount is used, but 2.1 to 4 times mol is preferable. The reaction temperature can be arbitrarily set from -20 ° C to 100 ° C, but preferably -5 to 10 ° C.
（式中Ｒ，Ｒ1，Ｒ2は前記と同じ意味を表す） 本製造法(b)においては上記反応式に示されるとおり、
一般式〔II〕で表される化合物を溶媒中で、一般式〔I
V〕で表される一般アミン例えばメチルアミン、エチル
アミン、アリルアミンおよび３７％ホルマリン液または
パラホルムアルデヒドと反応させることによって本発明
化合物を容易に得ることができる。溶媒としてはメタノ
ール、エタノール等のアルコール類、ジオキサン、テト
ラヒドロフラン等のエーテル類、水等を単独または混合
して使用することができる。反応温度は室温からその溶
媒の沸騰温度まで任意に設定できるが、好ましくは５０
〜１００℃が適当である。 (Wherein R, R 1 and R 2 have the same meanings as described above) In the present production method (b), as shown in the above reaction formula,
In a solvent, a compound represented by the general formula [II] is represented by the general formula [I
The compound of the present invention can be easily obtained by reacting with a general amine represented by V] such as methylamine, ethylamine, allylamine and a 37% formalin solution or paraformaldehyde. As the solvent, alcohols such as methanol and ethanol, ethers such as dioxane and tetrahydrofuran, water and the like can be used alone or in combination. The reaction temperature can be arbitrarily set from room temperature to the boiling temperature of the solvent, but is preferably 50
-100 ° C is suitable.
（式中Ｒ，Ｒ1，Ｒ2は前記と同じ意味を表わし、 Ｙはハロゲン原子、−OSO2CH3または で表される基を示す） 一般式〔Ｖ〕で表される化合物と一般式〔ＶＩ〕で表さ
れる化合物を、不活性溶媒中で塩基性物質の存在下に反
応させることによって本発明化合物を容易に得ることが
できる。溶媒としてはＤＭＦ，ＤＭＳＯ、アセトニトリ
ルまたはテトラヒドロフラン、ジオキサン等のエーテル
類を単独または混合して使用することができる。塩基性
物質としては水素化ナトリウム、炭酸カリウム、水酸化
ナトリウム等が使用でき、好ましくは1.1〜2.5倍モルが
適当である。反応温度は室温から１５０℃まで任意に設
定できるが、好ましくは４０〜１００℃が適当である。 (In the formula, R, R 1 and R 2 have the same meanings as described above, Y is a halogen atom, -OSO 2 CH 3 or The compound of the present invention is obtained by reacting a compound represented by the general formula [V] with a compound represented by the general formula [VI] in the presence of a basic substance in an inert solvent. Can be easily obtained. As the solvent, ethers such as DMF, DMSO, acetonitrile or tetrahydrofuran or dioxane can be used alone or in combination. As the basic substance, sodium hydride, potassium carbonate, sodium hydroxide and the like can be used, preferably 1.1 to 2.5 times by mole. The reaction temperature can be arbitrarily set from room temperature to 150 ° C, but is preferably 40 to 100 ° C.
本発明のヘキサヒドロトリアジン化合物は新規化合物で
ある。第１表に本発明の代表化合物を例示する。The hexahydrotriazine compound of the present invention is a novel compound. Table 1 illustrates representative compounds of the present invention.
本発明化合物はそれらの有効成分をそのままか、あるい
は慣用の製剤技術によって乳剤、水和剤、粉剤、粒剤、
フロアブル剤などの形態に製材したものを殺虫剤として
使用することができる。これらの製剤を造るに際して
は、液体または固体担体を使用することができる。液体
担体としては、有機溶媒があげられるが、例えばキシレ
ン、クロロベンゼン、メチルナフタレン、シクロヘキサ
ノン、イソホロン、アルコール類、ジメチルホルムアミ
ド、Ｎ−メチルピロリドン等が有利に使用される。固体
担体としては、例えばカオリン、タルク、ベントナイ
ト、ケイソウ土、クレーがあげられ、またアルミナ、ゼ
オライト、ケイ酸塩等の合成化合物も使用できる。これ
らの製剤に当たっては、乳化、分散、懸濁、浸透等の特
性を与えるために、各種の補助剤例えば乳化剤、分散
剤、展着剤、湿展剤、浸透剤等を使用することができ
る。 The compounds of the present invention may be used as they are as the active ingredients as they are, or by an ordinary formulation technique such as emulsion, wettable powder, powder, granule,
A material such as a flowable agent that has been sawn can be used as an insecticide. Liquid or solid carriers can be used in making these formulations. Examples of the liquid carrier include organic solvents, and for example, xylene, chlorobenzene, methylnaphthalene, cyclohexanone, isophorone, alcohols, dimethylformamide, N-methylpyrrolidone, etc. are advantageously used. Examples of the solid carrier include kaolin, talc, bentonite, diatomaceous earth and clay, and synthetic compounds such as alumina, zeolite and silicate can also be used. In these preparations, various auxiliary agents such as emulsifiers, dispersants, spreading agents, wetting agents, penetrating agents and the like can be used in order to impart characteristics such as emulsification, dispersion, suspension and penetration.
作用 前記の一般式〔Ｉ〕で表される本発明の化合物は半翅
目、鱗翅目、甲虫目、双翅目、直翅目、シロアリ目など
の各種の害虫に強い殺虫力を有し、また人畜に対する毒
性が低く植物に対する安全性が高いなどのすぐれた性質
を有する実用的な殺虫剤である。Action The compound of the present invention represented by the general formula [I] has a strong insecticidal activity against various pests such as Hemiptera, Lepidoptera, Coleoptera, Diptera, Orthoptera, and Termites, Further, it is a practical insecticide having excellent properties such as low toxicity to humans and animals and high safety to plants.
本発明の化合物が有効な害虫を例示すると以下のとおり
である。例えば、 トビイロウンカ(Nilaparvata lugens)、 ヒメトビウンカ(Laodelphax striatellus)、 ツマグロヨコバイ(Nephotettix cincticeps)、 クワコナカイガラムシ(Pseudococcus comstocki)、 ヤノネカイガラムシ(Unaspis yanonensis)、 モモアカアブラムシ(Myzus persicae)、 ワタアブラムシ(Aphis gossypii)、 ニセダイコンアブラムシ(Lipaphis erysimi)、 ナシグンバイムシ(Stephanitis nashi)、 イネクロカメムシ(Scotinophara lurids)、 オンシツコナジラミ(Trialeurodes vaporariorus)、 などの半翅目害虫、例えば、 アオムシ(Pieris rapae)、 ハスモンヨトウ(Spodoptera litura)、 ヨトウガ(Mamestra brassicae)、 ニカメイガ(Chilo suppressalis)、 コナガ(Plutella xyiostella)、 コカクモンハマキ(Adoxophyes orana)、 カブラヤガ(Agrotis segetum)、 コブノメイガ(Cnaphalocrocis medinalis)、 アワノメイガ(Ostrinia furnacalis)などの鱗翅目害
虫、例えば、 ニジュウヤホシテントウ(Henosepilachna vegintioctop
unctata)、 ウリハムシ(Aulacophora femoralis)、 キスジノミハムシ(Phyllotreta striolata)、 イネミズゾウムシ(Lissorhoptrus oryzophilus)、 コクゾウムシ(Sitophilus zeamais)、 ヒメコガネ(Anomala rufocuprea)などの甲虫目害虫、例
えば イエバエ(Musca domestica)、 タネバエ(Hylemia platura)、 アカイエカ(Culex pipiens)などの双翅目害虫、例え
ば、 ケラ(Gryllotalpa africana)、 チャバネゴキブリ(Blatella germanica)、 トノサマバッタ(Locusta migratoria)などの直翅目害
虫、例えば、 イエシロアリ(Coptotermes formosanus)、 ヤマトシロアリ(Reticulitermes speratus)などのシロ
アリ目害虫などを挙げることができる。Examples of pests for which the compound of the present invention is effective are as follows. For example, the brown planthopper (Nilaparvata lugens), the brown planthopper (Laodelphax striatellus), the leafhopper leafhopper (Nephotettix cincticeps), the stag beetle (Pseudococcus comstocki), Unaspis yanonensis (Unaspis moss) , Pteris rapera (Pieris rapae) (Pieris rapae) (Pieris rapae) (Pieris rapae) (Pieris rapae) rapae (Pieris rapae) , Spodoptera litura (Mamestra brassicae), Nikamai moth (Chilo suppressalis), diamondback moth (Plutella xyiostella), Red-spotted beetle (Adoxophyes orana), Kaburagaga (Agrotis segetum), Kobuno-maiga (Cnaphalocrocis medinalis), such as Crophalocrocis medinalis; D Henosepilachna vegintioctop
unctata), Acacophora femoralis, Phyllotreta striolata, Rice weevil, Lissorhoptrus oryzophilus, Sitophilus zeamais, Anomala rufocuprea, and other beetles such as Anomala rufocuprea. , Diptera pests such as Culex pipiens, for example, Gryllotalpa africana, Blattella germanica, Locusta migratoria, and other insect pests, such as Coptotermes formosanus, Reticulitermes speratus) and other termite pests.
実施例 次に合成例を挙げて本発明化合物の製造方法をさらに詳
細に説明する。Examples Next, the production method of the compound of the present invention will be described in more detail with reference to synthetic examples.
合成例１ １−（２−クロロ−５−ピリジルメチル）−３，５−ジ
メチル−２−ニトロイミノヘキサヒドロ−１，３，５−
トリアジンの合成 １，５−ジメチル−２−ニトロイミノヘキサヒドロ−
１，３，５−トリアジン１ｇを乾燥ＤＭＦ２０mlに溶解
し、氷冷下に６０％水素化ナトリウム0.27ｇを加え、水
素の発生が止むまで室温で１時間、５０℃でさらに１時
間加熱攪拌した。その後、２−クロロ−５−ピリジルメ
チルクロライド0.9ｇの乾燥ＤＭＦ８ml液を４０〜５０
℃で滴下した。滴下後、７０〜８０℃で２時間加熱攪拌
し、反応液を氷冷水にあけ、ジクロロメタンで抽出し
た。無水硫酸マグネシウムで乾燥後ジクロロメタンを留
去し、カラムクロマトグラフィーによって精製し、融点
１１６〜１１７℃の化合物番号１の目的物1.3ｇを得
た。Synthesis Example 1 1- (2-chloro-5-pyridylmethyl) -3,5-dimethyl-2-nitroiminohexahydro-1,3,5-
Synthesis of triazine 1,5-dimethyl-2-nitroiminohexahydro-
1 g of 1,3,5-triazine was dissolved in 20 ml of dry DMF, 0.27 g of 60% sodium hydride was added under ice cooling, and the mixture was heated with stirring at room temperature for 1 hour and at 50 ° C. for 1 hour until hydrogen generation stopped. Then, 40 ml of a dry DMF 8 ml solution containing 0.9 g of 2-chloro-5-pyridylmethyl chloride was used.
Dropwise at ° C. After the dropping, the mixture was heated with stirring at 70 to 80 ° C. for 2 hours, poured into ice-cooled water, and extracted with dichloromethane. After drying over anhydrous magnesium sulfate, dichloromethane was distilled off and the residue was purified by column chromatography to obtain 1.3 g of the desired product of Compound No. 1 having a melting point of 116 to 117 ° C.
合成例２ １−（２−クロロ−５−チアゾリルメチル）−３，５−
ジメチル−２−ニトロイミノヘキサヒドロ−１，３，５
−トリアジンの合成 １，５−ジメチル−２−ニトロイミノヘキサヒドロ−
１，３，５−トリアジン1.7ｇを乾燥ＤＭＦ２０mlに溶
解し、氷冷下に６０％水素化ナトリウム0.28ｇを少量づ
つ加え、水素の発生が止むまで室温で１時間、５０℃で
さらに１時間加熱攪拌した。その後２−クロロ−５−チ
アゾリルメチルクロライド1.7ｇの乾燥ＤＭＦ８ml液を
４０〜５０℃で滴下した。滴下後７０〜８０℃で２時間
攪拌し反応液を氷冷水にあけ、ジクロロメタンで抽出し
た。無水硫酸マグネシウムで乾燥後、ジクロロメタンを
留去し、カラムクロマトグラフィーによって精製し、融
点１２５〜１２６℃の化合物番号２の目的物0.82ｇを得
た。Synthesis Example 2 1- (2-chloro-5-thiazolylmethyl) -3,5-
Dimethyl-2-nitroiminohexahydro-1,3,5
-Synthesis of triazine 1,5-dimethyl-2-nitroiminohexahydro-
1.7 g of 1,3,5-triazine was dissolved in 20 ml of dry DMF, 0.28 g of 60% sodium hydride was added little by little under ice cooling, and the mixture was heated at room temperature for 1 hour and at 50 ° C for 1 hour until hydrogen generation stopped. It was stirred. Thereafter, a solution of 2-chloro-5-thiazolylmethyl chloride (1.7 g) in dry DMF (8 ml) was added dropwise at 40 to 50 ° C. After dropping, the mixture was stirred at 70 to 80 ° C. for 2 hours, poured into ice-cooled water, and extracted with dichloromethane. After drying over anhydrous magnesium sulfate, dichloromethane was distilled off and the residue was purified by column chromatography to obtain 0.82 g of the desired compound of Compound No. 2 having a melting point of 125 to 126 ° C.
次に具体的な製剤例を例示するが、添加する担体、界面
活性剤などはこれらの製剤例に限定されるものではな
い。Next, specific formulation examples are illustrated, but the carrier, surfactant, etc. to be added are not limited to these formulation examples.
製剤例１（水和剤） 化合物番号１の化合物32.5部、リグニンスルホン酸塩３
部、ポリオキシエチレンアルキルフェニルエーテル４
部、含水二酸化ケイ素２部およびクレー58.5部をよく混
合し、粉砕して水和剤を得た。Formulation Example 1 (wettable powder) Compound No. 1 compound 32.5 parts, lignin sulfonate 3
Part, polyoxyethylene alkyl phenyl ether 4
Parts, 2 parts of hydrous silicon dioxide and 58.5 parts of clay were mixed well and pulverized to obtain a wettable powder.
製剤例２（粉剤） 化合物番号２の化合物5.4部、含水二酸化ケイ素２部お
よびタルク92.6部をよく混合し、粉砕して粉剤を得た。Formulation Example 2 (Dust) 5.4 parts of the compound of Compound No. 2, 2 parts of hydrous silicon dioxide and 92.6 parts of talc were mixed well and pulverized to obtain a powder.
製剤例３（粒剤） 化合物番号３の化合物5.4部、リグニンスルホン酸塩３
部、ドデシルベンゼンスルホン酸ナトリウム１部、ベン
トナイト３０部およびクレー60.6部を良く粉砕混合し、
水を加えてよく練り合わせた後、造粒、乾燥して粒剤を
得た。Formulation Example 3 (granule) 5.4 parts of the compound of Compound No. 3, lignin sulfonate 3
Parts, 1 part of sodium dodecylbenzene sulfonate, 30 parts of bentonite and 60.6 parts of clay are well pulverized and mixed,
After adding water and kneading well, it was granulated and dried to obtain a granule.
次に本発明化合物の殺虫効果を試験例によって例示す
る。Next, the insecticidal effect of the compound of the present invention will be illustrated by test examples.
試験例１ 草丈７cm前後のイネ苗５本を１株として、製剤例１にも
とずいて製剤した各化合物の水和剤を水で希釈した所定
濃度の薬液に１０秒間浸漬した。風乾後、根部を水を含
ませた脱脂綿で巻いて直径３cm、高さ２０cmのガラス円
筒に入れ、薬剤抵抗性ツマグロヨコバイ２令幼虫を１０
頭放飼し２６℃の定温室内に静置した。４８時間後に生
死虫数を調査した。結果を第２表に示す。Test Example 1 Five rice seedlings having a plant height of about 7 cm were used as one strain, and a wettable powder of each compound prepared according to Preparation Example 1 was immersed in a chemical solution of a predetermined concentration diluted with water for 10 seconds. After air-drying, the roots are wrapped with absorbent cotton soaked in water and placed in a glass cylinder with a diameter of 3 cm and a height of 20 cm.
The head was released and left standing in a constant temperature room at 26 ° C. The number of live and dead insects was investigated 48 hours later. The results are shown in Table 2.
第２表の比較化合物は次の化合物である。 The comparative compounds in Table 2 are the following compounds.
試験例２ 草丈７cm前後のイネ苗５本を１株として、製剤例１にも
とずいて製剤した各化合物の水和剤を水で希釈した所定
濃度の薬液に１０秒間浸漬した。風乾後、根部を水を含
ませた脱脂綿で巻いて直径３cm、高さ２０cmのガラス円
筒に入れ、薬剤抵抗性トビイロウンカ２令幼虫を１０頭
放飼し２６℃の定温室内に静置した。４８時間後に生死
虫数を調査した。結果を第３表に示す。 Test Example 2 Five rice seedlings having a plant height of about 7 cm were used as one strain, and a wettable powder of each compound prepared according to Preparation Example 1 was immersed in a chemical solution of a predetermined concentration diluted with water for 10 seconds. After air-drying, the root part was wrapped with absorbent cotton soaked in water and placed in a glass cylinder having a diameter of 3 cm and a height of 20 cm, and 10 second-instar larvae of the drug-resistant brown planthopper were released and allowed to stand in a constant temperature room at 26 ° C. The number of live and dead insects was investigated 48 hours later. The results are shown in Table 3.
第３表の比較化合物は第２表の比較化合物と同じであ
る。 The comparative compounds in Table 3 are the same as the comparative compounds in Table 2.
効果 一般式〔Ｉ〕で表される本発明化合物は、各種の害虫に
対して極めて高い殺虫効力を有し、また温血動物に対す
る毒性、魚類、甲殻類などに対する毒性が低く、残留が
少なく、植物に対する安全性の高い、新規殺虫剤であ
る。Effect The compound of the present invention represented by the general formula [I] has extremely high insecticidal activity against various pests, low toxicity to warm-blooded animals, low toxicity to fish, crustaceans, etc. It is a new insecticide with high plant safety.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 瀬上 繁則 埼玉県所沢市山口137 ハイムＨ．Ｔ２― 203 (72)発明者 南條 勝美 埼玉県所沢市下安松1563―７ (72)発明者 佐藤 潤子 東京都国立市西１―17―30―201 (56)参考文献 特開 平２−235881（ＪＰ，Ａ) 国際公開第91／01987（ＷＯ，Ａ) ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Shigenori Segami 137 Yamaguchi, Tokorozawa, Saitama Prefecture Heim H. T2-203 (72) Inventor Katsumi Nanjo 1563-7 Shimoyasumatsu Tokorozawa, Saitama Prefecture (72) Inventor Junko Sato 1-17-30-201 (56) Nishi, National City of Tokyo Reference: JP-A-2-235881 ( JP, A) International Publication No. 91/01987 (WO, A)
Claims (5)
し、Ｒ1は低級アルキル基、低級アルケニル基または低
級アルキニル基を示し、 Ｒ2は または で表される基を示す） で表されるヘキサヒドロトリアジン化合物。1. A general formula [I] (In the formula, R represents a lower alkyl group or a lower alkenyl group, R 1 represents a lower alkyl group, a lower alkenyl group or a lower alkynyl group, and R 2 represents Or A hexahydrotriazine compound represented by:
低級アルキニル基を示し、 Ｒ2は または で表される基を示す） で表される化合物と、一般式〔III〕 R-N(CH2X)2 〔III〕 （式中Ｒは低級アルキル基または低級アルケニル基を示
し、Ｘはハロゲン原子を示す） で表される化合物とを反応させることを特徴とする一般
式〔Ｉ〕 （式中Ｒは低級アルキル基または低級アルケニル基を示
し、Ｒ1は低級アルキル基、低級アルケニル基または低
級アルキニル基を示し、 Ｒ2は または で表される基を示す） で表されるヘキサヒドロトリアジン化合物の製造法。2. General formula [II] (In the formula, R 1 represents a lower alkyl group, a lower alkenyl group or a lower alkynyl group, and R 2 represents Or And a compound represented by the general formula [III] RN (CH 2 X) 2 [III] (wherein R represents a lower alkyl group or a lower alkenyl group, and X represents a halogen atom). The compound represented by the formula (1) is reacted with a compound represented by the general formula [I] (In the formula, R represents a lower alkyl group or a lower alkenyl group, R 1 represents a lower alkyl group, a lower alkenyl group or a lower alkynyl group, and R 2 represents Or Represents a group represented by) The method for producing a hexahydrotriazine compound represented by:
低級アルキニル基を示し、 Ｒ2は または で表される基を示す） で表される化合物と、一般式〔IV〕 R-NH2 〔IV〕 （式中Ｒは低級アルキル基または低級アルケニル基を示
す） で表される一級アミン類とホルマリンまたはパラホルム
アルデヒドとを反応させることを特徴とする一般式
〔Ｉ〕 （式中Ｒは低級アルキル基または低級アルケニル基を示
し、Ｒ1は低級アルキル基、低級アルケニル基または低
級アルキニル基を示し、 Ｒ2は または で表される基を示す） で表されるヘキサヒドロトリアジン化合物の製造法。3. General formula [II] (In the formula, R 1 represents a lower alkyl group, a lower alkenyl group or a lower alkynyl group, and R 2 represents Or And a primary amine represented by the general formula [IV] R-NH 2 [IV] (wherein R represents a lower alkyl group or a lower alkenyl group). General formula [I] characterized by reacting with formalin or paraformaldehyde (In the formula, R represents a lower alkyl group or a lower alkenyl group, R 1 represents a lower alkyl group, a lower alkenyl group or a lower alkynyl group, and R 2 represents Or Represents a group represented by) The method for producing a hexahydrotriazine compound represented by:
し、Ｒ1は低級アルキル基、低級アルケニル基または低
級アルキニル基を示す） で表される化合物と、一般式〔VI〕 R2CH2-Y 〔VI〕 （式中Ｒ2は または で表される基を示し、Ｙはハロゲン原子、−OSO2CH3ま
たは で表される基を示す） で表される化合物とを反応させることを特徴とする一般
式〔Ｉ〕 （式中Ｒは低級アルキル基または低級アルケニル基を示
し、Ｒ1は低級アルキル基、低級アルケニル基または低
級アルキニル基を示し、 Ｒ2は または で表される基を示す） で表されるヘキサヒドロトリアジン化合物の製造法。4. A general formula [V] (Wherein R represents a lower alkyl group or a lower alkenyl group, and R 1 represents a lower alkyl group, a lower alkenyl group or a lower alkynyl group), and a compound represented by the general formula [VI] R 2 CH 2 -Y [VI] (wherein R 2 is Or Represents a group represented by, Y is a halogen atom, -OSO 2 CH 3 or A compound represented by the formula (I) is reacted with a compound represented by the formula (I) (In the formula, R represents a lower alkyl group or a lower alkenyl group, R 1 represents a lower alkyl group, a lower alkenyl group or a lower alkynyl group, and R 2 represents Or Represents a group represented by) The method for producing a hexahydrotriazine compound represented by:
し、Ｒ1は低級アルキル基、低級アルケニル基または低
級アルキニル基を示し、 Ｒ2は または で表される基を示す） で表されるヘキサヒドロトリアジン化合物を活性成分と
して含有することを特徴とする殺虫剤。5. A general formula [I] (In the formula, R represents a lower alkyl group or a lower alkenyl group, R 1 represents a lower alkyl group, a lower alkenyl group or a lower alkynyl group, and R 2 represents Or An insecticide comprising a hexahydrotriazine compound represented by the formula (1) as an active ingredient.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/606,848 US6187773B1 (en) | 1989-11-10 | 1990-10-31 | Hexahydrotriazine compounds and insecticides |
| AU65623/90A AU628229B2 (en) | 1989-11-10 | 1990-10-31 | Hexahydrotriazine compounds and insecticides |
| DE69019107T DE69019107T2 (en) | 1989-11-10 | 1990-11-08 | Hexahydrotriazine compounds and insecticides. |
| EP90121383A EP0428941B1 (en) | 1989-11-10 | 1990-11-08 | Hexahydrotriazine compounds and insecticides |
| KR1019900018143A KR0147056B1 (en) | 1989-11-10 | 1990-11-09 | Hexa hydro triazine compounds and insecticides |
| CN90109039A CN1026648C (en) | 1989-11-10 | 1990-11-10 | Hexahydrotriazine compounds and insecticides |
| CN94103331A CN1050600C (en) | 1989-11-10 | 1994-03-25 | Hexahydrotriazine compounds and insecticides |
| US09/729,865 US20010046994A1 (en) | 1989-11-10 | 2000-12-06 | Hexahydrotriazine compounds and insecticides |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1-292675 | 1989-11-10 | ||
| JP29267589 | 1989-11-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03218370A JPH03218370A (en) | 1991-09-25 |
| JPH06776B2 true JPH06776B2 (en) | 1994-01-05 |
Family
ID=17784845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024199A Expired - Fee Related JPH06776B2 (en) | 1989-11-10 | 1990-02-02 | Hexahydrotriazine compound, its production method and insecticide |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPH06776B2 (en) |
| KR (1) | KR0147056B1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08245314A (en) * | 1995-03-09 | 1996-09-24 | Sumitomo Chem Co Ltd | Method for hemiptera insect pest control in paddy field |
| JP2007153911A (en) * | 2007-03-16 | 2007-06-21 | Sumitomo Chemical Co Ltd | Method of controlling hemipteran insect pest in paddy field |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2610988B2 (en) * | 1989-03-09 | 1997-05-14 | 日本バイエルアグロケム 株式会社 | New heterocyclic compounds and insecticides |
-
1990
- 1990-02-02 JP JP2024199A patent/JPH06776B2/en not_active Expired - Fee Related
- 1990-11-09 KR KR1019900018143A patent/KR0147056B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR0147056B1 (en) | 1998-08-17 |
| JPH03218370A (en) | 1991-09-25 |
| KR910009690A (en) | 1991-06-28 |
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