JP2819304B2 - Hexahydrotriazinone derivatives and selective herbicides containing the same as an active ingredient - Google Patents
Hexahydrotriazinone derivatives and selective herbicides containing the same as an active ingredientInfo
- Publication number
- JP2819304B2 JP2819304B2 JP12184489A JP12184489A JP2819304B2 JP 2819304 B2 JP2819304 B2 JP 2819304B2 JP 12184489 A JP12184489 A JP 12184489A JP 12184489 A JP12184489 A JP 12184489A JP 2819304 B2 JP2819304 B2 JP 2819304B2
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- JP
- Japan
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- compound
- hexahydrotriazinone
- active ingredient
- present
- same
- 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.)
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Description
【発明の詳細な説明】 産業上の利用分野 本発明は除草作用等の生理活性を有する新規なヘキサ
ヒドロトリアジノン誘導体及びそれを有効成分として含
有する選択性除草剤に関する。さらに詳細には本発明
は、 一般式 （但し、式中R1は で表わされるピラゾール基または で表わされるベンジル基を示す。） で表わされるヘキサヒドロトリアジノン誘導体（以下、
本発明化合物という）およびこれを有効成分として含有
する選択性除草剤に関する。Description: TECHNICAL FIELD The present invention relates to a novel hexahydrotriazinone derivative having a physiological activity such as herbicidal action and a selective herbicide containing the same as an active ingredient. More specifically, the present invention provides a compound of the general formula (However, in the formula, R 1 is A pyrazole group represented by Represents a benzyl group represented by The hexahydrotriazinone derivative represented by
And a selective herbicide containing the same as an active ingredient.
従来の技術 いくつかの置換ヘキサヒドロトリアジノン誘導体が知
られている。例えば４−アミノ−６−tert−ブチル−３
−メチルチオ−1,2,4−トリアジン−５（4H）−オン（S
encor）がダイズ、トマト、ニンジン、ソルガムなどの
作物の発芽前、発芽後の除草剤として使用できることは
既に開示されている（西独特許1,542,873号、米国特許
3,671,523号）。しかしながらSencorはその非選択的な
除草作用のために稲、小麦、トウモロコシなどの主要作
物にも影響を及ぼす。しかも作用が効果的でない上に極
めて水によく溶けるので、降雨などの自然現象により土
壌から流亡され易いという欠点がある。PRIOR ART Several substituted hexahydrotriazinone derivatives are known. For example, 4-amino-6-tert-butyl-3
-Methylthio-1,2,4-triazin-5 (4H) -one (S
encor) can be used as a herbicide before and after germination of crops such as soybean, tomato, carrot and sorghum (West German Patent 1,542,873, US Patent)
3,671,523). However, Sencor also affects key crops such as rice, wheat and corn due to its non-selective herbicidal action. In addition, it has an ineffective function and is extremely well soluble in water, so that it has a drawback that it is easily washed away from soil by natural phenomena such as rainfall.
発明が解決しようとする課題 本発明の目的は優れた除草活性を有し、しかも作物に
薬害の無い選択性除草剤を提供することにある。DISCLOSURE OF THE INVENTION An object of the present invention is to provide a selective herbicide having excellent herbicidal activity and having no harm to crops.
課題を解決するための手段 本発明者等は優れた除草活性を有し、しかも作物に薬
害のない選択性除草剤の開発をめざし種々研究を重ねた
結果、前記一般式で表わされるヘキサヒドロトリアジノ
ン誘導体が強力な殺草力を有し、しかも稲、小麦、大
麦、トウモロコシ等の作物に対して薬害がなく、高い選
択的除草作用を示すことを見出して本発明を完成した。
しかもSencorが水溶性が高く、降雨によって土壌から流
亡され易い欠点があるのに対して、本発明化合物は水に
対して不溶であるため土壌から流亡し効果を半減するこ
とはない。Means for Solving the Problems The inventors of the present invention have conducted various studies with the aim of developing a selective herbicide having excellent herbicidal activity and having no phytotoxicity to crops. The present invention has been completed by finding that a dinone derivative has a strong herbicidal activity, has no phytotoxicity to crops such as rice, wheat, barley, and corn and exhibits a high selective herbicidal action.
In addition, Sencor has a high water solubility and has a disadvantage that it is easily run off from the soil by rainfall. On the other hand, the compound of the present invention is insoluble in water and does not run off the soil by half.
本発明化合物は一般式 （但し、式中R1は で表わされるピラゾール基または で表わされるベンジル基を示す。） で表わされる化合物をマンニッヒ反応条件下でホルムア
ルデヒドおよびメチルアミンと反応させることによって
得られる。ホルムアルデヒドは水溶液の状態で用いるこ
とができる。本反応は好ましくはアルコールなど例えば
メタノールのような不活性溶媒中で実施される。適当な
反応温度は０℃から100℃であり、好ましくは50℃前後
である。The compound of the present invention has the general formula (However, in the formula, R 1 is A pyrazole group represented by Represents a benzyl group represented by ) Is reacted with formaldehyde and methylamine under Mannich reaction conditions. Formaldehyde can be used in the form of an aqueous solution. This reaction is preferably carried out in an inert solvent such as an alcohol such as methanol. Suitable reaction temperatures are from 0 ° C to 100 ° C, preferably around 50 ° C.
本発明化合物は反応混合物を常法で精製することによ
って得ることが出来る。The compound of the present invention can be obtained by purifying the reaction mixture by a conventional method.
本発明化合物はつぎの２つの化合物である。 The compound of the present invention is the following two compounds.
３−〔（２−カルボメトキシベンジル）スルホニル〕
−５−メチル−１−（4,6−ジメトキシ−1,3−ピリミジ
ン−２−イル）−1,3,5−ヘキサヒドロトリアジン−２
−オン（化合物番号１） ３−［（１−メチル−４−カルボエトキシ−ピラゾー
ル−５−イル）スルホニル］−５−メチル−１−（4,6
−ジメトキシ−1,3−ピリミジン−２−イル）−1,3,5−
ヘキサヒドロトリアジン−２−オン（化合物番号２） 本発明化合物は極めて低薬量で広範囲の雑草、例えば
タマガヤツリ、イヌホタルイ、コナギ、ウリカワ、マツ
バイ、ミズガヤツリ、クログワイ、ヘラオモダカ、オモ
ダカ、アゼナ、キカシグサ、ヒルムシロ、チョウジタ
デ、ミズハコベ等の水田雑草、アオビユ、イチビ、アカ
ザ、イヌタデ、スベリヒユ、シロバナチョウセンアサガ
オ、マルバアサガオ、オナモミ、ハマスゲ、ブラックグ
ラス、ウマノチャヒキ、コハコベ、カラシナ類、エビス
グサ、カミツレ、ツユクサ等の畑地雑草に対して優れた
殺草力を有するのみならず、稲、大麦、小麦、トウモロ
コシ等の作物に対して薬害はなく、極めて安全に使用す
ることができる。また本発明化合物は作物と各種雑草と
の間に優れた選択的活性を示し、哺乳動物や魚貝類に対
して低毒性であり、低薬量処理なので環境汚染も少な
く、水田、畑、果樹園或いは非農耕地用の除草剤として
安全に使用することができる。3-[(2-carbomethoxybenzyl) sulfonyl]
-5-methyl-1- (4,6-dimethoxy-1,3-pyrimidin-2-yl) -1,3,5-hexahydrotriazine-2
-One (Compound No. 1) 3-[(1-methyl-4-carbethoxy-pyrazol-5-yl) sulfonyl] -5-methyl-1- (4,6
-Dimethoxy-1,3-pyrimidin-2-yl) -1,3,5-
Hexahydrotriazin-2-one (Compound No. 2) The compound of the present invention has a very low dose and a wide range of weeds, for example, stag beetle, scallop, scallop, urikawa, pine bye, sylvestris, kuroguwai, hera omodaka, omodaka, azena, kikasigusa, hirumushiro, Paddy field weeds such as Clovergrass, Mizuhakobe, Aoyuyu, Ichibi, Akaza, Inutade, Purslane, Shirobanachosen Asagao, Marubaasagao, Onamimomi, Hamasuge, Blackgrass, Umanachakiki, Kohakobe, Japanese mustard, Ebisugusa Not only has excellent herbicidal activity but also has no phytotoxicity to crops such as rice, barley, wheat, and corn, and can be used extremely safely. In addition, the compound of the present invention exhibits excellent selective activity between crops and various weeds, has low toxicity to mammals and fish and shellfish, and has low environmental treatment due to low-dose treatment, so that it can be used in paddy fields, fields, orchards. Alternatively, it can be safely used as a herbicide for non-agricultural land.
本発明化合物を除草剤として使用する場合、一般の農
薬と同様の形態、すなわち本発明化合物の１種または２
種をその使用目的によって適当な液体担体に溶解する
か、分散させるか、または適当な固体担体と混合するか
吸着させ、乳剤、油剤、水和剤、粉剤、粒剤、錠剤等の
製剤として使用する。これらの製剤は必要に応じ、乳化
剤、湿潤剤、安定剤等を添加してもよく、当業界に公知
の方法で製剤することができる。使用する液体担体とし
ては、例えば水、アルコール類、ケトン類、エーテル
類、脂肪族炭化水素類、芳香族炭化水素類、ハロゲン化
炭化水素類、酸アミド類、エステル類、ニトリル類等の
溶剤が使用され、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。固体担体としては、植物性粉
末やクレイ類、タルク類、シリカ類、珪藻土等の鉱物性
粉末やアルミナ、活性炭等が使用され、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。乳化
剤、展着剤、浸透剤、分散剤等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、ポリオキシエチレンア
リールエステル類、アルキル硫酸塩類、アルキルスルホ
ン酸塩類、ポリエチレングリコールエーテル類、多価ア
ルコールエステル類等の非イオン系およびアニオン系界
面活性剤が用いられる。When the compound of the present invention is used as a herbicide, it may be in the same form as a general pesticide, that is, one or two of the compounds of the present invention.
The seed is dissolved or dispersed in a suitable liquid carrier or mixed or adsorbed with a suitable solid carrier depending on the purpose of use, and used as a formulation for emulsions, oils, wettable powders, powders, granules, tablets and the like. I do. These preparations may contain an emulsifier, a wetting agent, a stabilizer and the like, if necessary, and can be prepared by a method known in the art. Examples of the liquid carrier used include water, solvents such as alcohols, ketones, ethers, aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, acid amides, esters, and nitriles. These are used alone or in combination of two or more at an appropriate ratio. As the solid carrier, mineral powders such as vegetable powders, clays, talcs, silicas, diatomaceous earth, alumina, activated carbon and the like are used, and these are used alone or in a mixture of two or more at an appropriate ratio. I do. Surfactants used as emulsifiers, spreading agents, penetrants, dispersants and the like include soaps, polyoxyethylene alkyl aryl ethers, polyoxyethylene aryl esters, alkyl sulfates, alkyl sulfones as necessary. Nonionic and anionic surfactants such as acid salts, polyethylene glycol ethers and polyhydric alcohol esters are used.
本発明化合物を除草剤として用いる場合の使用量は、
適用場面、適用時期、適用方法、対象草種、栽培作物等
によりかなりの差異はあるが、一般的には有効成分（す
なわち本発明化合物）として水田１アール当たり0.05g
から50g程度、好ましくは0.1gから5g位、畑地１アール
当たり0.05gから30g程度、好ましくは0.1gから5g位の処
理量が適当である。The amount used when the compound of the present invention is used as a herbicide,
Although there are considerable differences depending on the application scene, application time, application method, target grass species, cultivated crops, etc., generally, 0.05 g per 1 paddy field as an active ingredient (namely, the compound of the present invention).
To about 50 g, preferably about 0.1 g to 5 g, and about 0.05 g to 30 g, preferably about 0.1 g to 5 g per field of field.
本発明化合物は水田雑草用としては発芽前土壌処理或
いは発芽後茎葉兼土壌処理剤として使用するのが適当で
ある。本発明の除草剤は必要に応じて他の除草剤、植物
生育調節剤、殺菌剤、殺虫剤、殺線虫剤、共力剤、肥料
等と混合して使用することができる。The compound of the present invention is suitable for paddy field weeds as a soil treatment before germination or as a foliage and soil treatment agent after germination. The herbicide of the present invention can be used in admixture with other herbicides, plant growth regulators, fungicides, insecticides, nematicides, synergists, fertilizers, and the like, if necessary.
実施例 つぎに本発明化合物の合成例、製剤例および除草試験
例をあげて本発明をさらに説明する。EXAMPLES Next, the present invention will be further described with reference to Synthesis Examples, Preparation Examples, and Herbicidal Test Examples of the compound of the present invention.
合成例１ ３−〔（２−カルボメトキシベンジル）スルホニル〕
−５−メチル−１−（4,6−ジメトキシ−1,3−ピリミジ
ン−２−イル）−1,3,5−ヘキサヒドロトリアジン−２
−オン（化合物番号１の製造） ２｛〔（4,6−ジメトキシ−ピリミジン−２−イル）
アミノカルボニル〕アミノスルホニルメチル｝安息香酸
メチルエステル3gをメタノール30mlに溶解し、37％ホル
マリンおよび40％メチルアミン水溶液30mlを加え、50℃
で一時間撹拌した。その反応液を濃縮後シリカゲルのカ
ラムクロマトグラフィーで精製することにより目的化合
物200mgを得た。融点161℃ 合成例２ ３−［（１−メチル−４−カルボエトキシ−ピラゾー
ル−５−イル）スルホニル］−５−メチル−１−（4,6
−ジメトキシ−1,3−ピリミジン−２−イル）−1,3,5−
ヘキサヒドロトリアジン−２−オン（化合物番号２の製
造） Ｎ−〔（4,6−ジメトキシピリミジン−２−イル）ア
ミノカルボニル〕−４−エトキシカルボニル−１−メチ
ル−５−ピラゾールスルホンアミド1gをメタノール10ml
に溶解し、37％ホルマリン10mlおよび40％メチルアミン
水溶液10mlを加え、50℃で一時間撹拌した。その反応液
を濃縮後アルミナのカラムクロマトグラフィーで精製す
ることにより目的化合物60mgを得た。融点86〜88℃ 製剤例１（乳剤） 有効成分５重量部、キシレン75重量部およびソルポー
ル2806B（商品名：東邦化学工業製界面活性剤）20重量
部を均一に撹拌混合して乳剤とする。Synthesis Example 1 3-[(2-carbomethoxybenzyl) sulfonyl]
-5-methyl-1- (4,6-dimethoxy-1,3-pyrimidin-2-yl) -1,3,5-hexahydrotriazine-2
-One (Production of compound No. 1) 2 ｛[(4,6-dimethoxy-pyrimidin-2-yl)
[Aminocarbonyl] aminosulfonylmethyl｝ benzoic acid methyl ester (3 g) was dissolved in methanol (30 ml), and 37% formalin and 40% methylamine aqueous solution (30 ml) were added.
For 1 hour. The reaction mixture was concentrated and purified by silica gel column chromatography to obtain 200 mg of the desired compound. Melting point 161 ° C. Synthesis Example 2 3-[(1-methyl-4-carbethoxy-pyrazol-5-yl) sulfonyl] -5-methyl-1- (4,6
-Dimethoxy-1,3-pyrimidin-2-yl) -1,3,5-
Hexahydrotriazin-2-one (Production of Compound No. 2) N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -4-ethoxycarbonyl-1-methyl-5-pyrazolesulfonamide (1 g) in methanol 10ml
And 10 ml of 37% formalin and 10 ml of a 40% aqueous methylamine solution were added thereto, followed by stirring at 50 ° C. for 1 hour. The reaction solution was concentrated and purified by alumina column chromatography to obtain 60 mg of the desired compound. Melting point 86-88 ° C. Formulation Example 1 (emulsion) 5 parts by weight of the active ingredient, 75 parts by weight of xylene, and 20 parts by weight of Solpol 2806B (trade name, manufactured by Toho Chemical Industry Co., Ltd.) are uniformly stirred and mixed to form an emulsion.
製剤例２（水和剤） 有効成分40重量部、ジークライト（商品名：ジークラ
イト工業製カオリン系クレー）54重量部、カープレック
ス（商品名：塩野義製薬製ホワイトカーボン）４重量部
およびソルポール5039（商品名：東邦化学工業製界面活
性剤）２重量部を混合粉砕して水和剤とする。Formulation Example 2 (Wettable powder) 40 parts by weight of active ingredient, 54 parts by weight of Sigleite (trade name: kaolin clay manufactured by Sigleite Industries), 4 parts by weight of Carplex (trade name: white carbon manufactured by Shionogi & Co., Ltd.) and Solpol 239 parts by weight of 5039 (trade name: surfactant manufactured by Toho Chemical Industry) are mixed and pulverized to obtain a wettable powder.
試験例１ 1/5000アールワグネルポットに水田土壌を詰め、表層
を軽く代掻きした後、ミゾハコベ、キカシグサ、コナ
ギ、タマガヤツリ等の１年生雑草およびホタルイ、ウリ
カワ、ミズガヤツリ、ヘラオモダカ、クログワイ等の多
年生雑草の種子や塊茎を播種した。さらに2.5葉期の水
稲（品種：ササニシキ）をポット当たり２本移植し湛水
深を4.0cmとした。水稲移植後３日目に本発明化合物の
所定量を処理し、処理後21日に肉眼観察により調査し、
表−１の結果を得た。評価は０（無処理同様）〜５（完
全抑制）の６段階で行った。Test Example 1 After filling paddy field soil in a 1/5000 are Wagner pot and lightly scratching the surface layer, seeds of annual weeds such as Mizohakobe, Kikasigusa, Konagi, Tamayatsuri and perennial weeds such as firefly, urikawa, mizugayatsuri, haramodaka, kuroguwai etc. And tubers were sown. Further, two rice plants of 2.5 leaf stage (variety: Sasanishiki) were transplanted per pot, and the flooding depth was set to 4.0 cm. A predetermined amount of the compound of the present invention was treated on the third day after the transplantation of the paddy rice, and examined by visual observation 21 days after the treatment,
The results in Table 1 were obtained. The evaluation was performed in six stages from 0 (same as no treatment) to 5 (complete suppression).
試験例２ 16cm×22cmバットに畑土壌を詰め、稲、麦、トウモロ
コシ、アオビユ、アカザ、タデ、オナモミ、ハコベ等の
種子を播種し、0.5cmの厚さに覆土をした。作物や雑草
の発芽前に本発明化合物の所定量を処理し、処理後21日
に肉眼観察により調査し、表−２の結果を得た。評価は
試験例１と同様に行った。 Test Example 2 A field soil was packed in a 16 cm × 22 cm vat, and seeds such as rice, wheat, corn, aobil, akaza, pomegranate, onion fir and chickweed were sowed and covered with a 0.5 cm thick soil. A predetermined amount of the compound of the present invention was treated before germination of crops and weeds, and examined by visual observation 21 days after the treatment, and the results in Table 2 were obtained. The evaluation was performed in the same manner as in Test Example 1.
発明の効果 本発明化合物は表−１および表−２に示すように水稲
用除草剤としても畑用除草剤としても優れた殺草作用を
示し、しかも稲、小麦、大麦、トウモロコシ等の作物に
対して実質的に薬害の無い、極めて優れた選択性除草剤
を提供することができる。 Effect of the Invention As shown in Tables 1 and 2, the compound of the present invention exhibits excellent herbicidal action as a herbicide for paddy rice and as a herbicide for fields, and it is effective for crops such as rice, wheat, barley, and corn. On the other hand, it is possible to provide an extremely selective herbicide having substantially no phytotoxicity.
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.6，ＤＢ名) C07D 403/04 C07D 403/14 ＣＡ、ＲＥＧＩＳＴＲＹ（ＳＴＮ)──────────────────────────────────────────────────続 き Continued on the front page (58) Fields surveyed (Int. Cl. 6 , DB name) C07D 403/04 C07D 403/14 CA, REGISTRY (STN)
Claims (2)
分として含有することを特徴とする選択性除草剤。2. The general formula (However, in the formula, R 1 is A pyrazole group represented by Represents a benzyl group represented by ) A selective herbicide comprising a hexahydrotriazinone derivative represented by the formula (1) as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12184489A JP2819304B2 (en) | 1989-05-16 | 1989-05-16 | Hexahydrotriazinone derivatives and selective herbicides containing the same as an active ingredient |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12184489A JP2819304B2 (en) | 1989-05-16 | 1989-05-16 | Hexahydrotriazinone derivatives and selective herbicides containing the same as an active ingredient |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02304082A JPH02304082A (en) | 1990-12-17 |
| JP2819304B2 true JP2819304B2 (en) | 1998-10-30 |
Family
ID=14821335
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12184489A Expired - Lifetime JP2819304B2 (en) | 1989-05-16 | 1989-05-16 | Hexahydrotriazinone derivatives and selective herbicides containing the same as an active ingredient |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2819304B2 (en) |
-
1989
- 1989-05-16 JP JP12184489A patent/JP2819304B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02304082A (en) | 1990-12-17 |
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