JPS6241592B2 - - Google Patents

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Publication number
JPS6241592B2
JPS6241592B2 JP11324380A JP11324380A JPS6241592B2 JP S6241592 B2 JPS6241592 B2 JP S6241592B2 JP 11324380 A JP11324380 A JP 11324380A JP 11324380 A JP11324380 A JP 11324380A JP S6241592 B2 JPS6241592 B2 JP S6241592B2
Authority
JP
Japan
Prior art keywords
formula
herbicide
compound
present
weeds
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
Application number
JP11324380A
Other languages
Japanese (ja)
Other versions
JPS5738778A (en
Inventor
Akira Nakamura
Matsuo Ono
Shigeo Aoki
Toshihide Ataka
Yasuhiro Ogino
Hirozo Segawa
Tetsuo Takematsu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kyowa Gas Chemical Industry Co Ltd
Original Assignee
Kyowa Gas Chemical Industry Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Kyowa Gas Chemical Industry Co Ltd filed Critical Kyowa Gas Chemical Industry Co Ltd
Priority to JP11324380A priority Critical patent/JPS5738778A/en
Publication of JPS5738778A publication Critical patent/JPS5738778A/en
Publication of JPS6241592B2 publication Critical patent/JPS6241592B2/ja
Granted legal-status Critical Current

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Description

【発明の詳现な説明】[Detailed description of the invention]

本発明は新芏なピラゞン誘導䜓に関し、さらに
詳しくは、―シアノピラゞン誘導䜓および該化
合物を有効成分ずする陀草剀に関する。 本発明に埓えば、䞀般匏 〔匏䞭、R1ぱチル基もしくは―プロピル
基を衚わし、R2は氎玠原子、ハロゲン原子、た
たはメチル基を衚わす〕 で瀺される―シアノピラゞン誘導䜓が提䟛され
る。 匏で瀺される䞀矀の―シアノピラゞン
誘導䜓は文献未茉の新芏化合物であり、今回、本
発明者らにより該化合物が陀草剀の有効成分ずし
お、すぐれた陀草掻性を有するこずが芋出され
た。特に、氎田湛氎土壌凊理、畑地土壌凊理にお
いお、匏の化合物は土壌衚局に堅固な薬剀
凊理局を圢成し、䟋えば移怍むネには実質的に無
害で、ノビ゚をはじめずする䞀幎生雑草を芋事に
防陀する胜力を有するこずが刀明した。 前蚘䞀般匏においお甚いる「ハロゲン原
子」ずしおはフツ玠、塩玠、シナり玠、ペり玠を
あげるこずができ、䞭でもフツ玠原子たたは塩玠
原子が奜たしい。 本発明の―シアノピラゞン誘導䜓は、䟋えば
䞋蚘匏で瀺されるそれ自䜓公知の化合物
―ゞシアノピラゞン誘導䜓特開昭54―
106479号、特開昭55―45634号明现曞を参照を
出発原料ずしお甚い、加氎分解反応、脱炭酞反応
および脱氎反応により補造される。 〔匏䞭、R1R2は前蚘の意味を有する〕 䞊蚘匏の化合物の加氎分解反応は、アル
カリ金属氎酞化物もしくはアルカリ土類金属炭酞
塩を氎及び又はメタノヌル、゚タノヌルなどのア
ルコヌル類䞭で䜜甚させるこずにより行うこずが
できる。 䞀般に−CN基は加氎分解によ぀お−CONH2基
になるが、−CONH2基は曎に加氎分解をうけお−
COOH基を生成しやすい。埓぀お−CN基を加氎
分解しお䞀方を−CONH2基に、他方を−COOH
基に加氎分解するためには、反応条件を厳遞する
必芁があり、甚いるアルカリ金属氎酞化物もしく
はアルカリ土類金属炭酞塩ずしおは氎酞化ナトリ
りム、氎酞化カリりム、氎酞化カルシりム、炭酞
ナトリりム、炭酞カリりムをあげるこずができ、
䞭でも氎酞化ナトリりムが奜たしく、その䜿甚量
は䞀般に匏の化合物モルに察し圓モル〜
1.5モルを䜿甚するのが有利である。䞊蚘加氎分
解反応は、宀枩から反応混合物の還流枩床におい
お、奜たしくは、還流枩床䞋に通垞〜時間の
反応時間に行なうこずができる。 かくしお埗られる匏の化合物はそれ自䜓
公知の手段、䟋えば再結晶、抜出たたはクロマト
グラフむヌ等の手段により粟補するこずができ
る。 〔匏䞭、R1R2は前蚘の意味を有する〕 次に匏の化合物の脱炭酞反応は、䞍掻性
溶媒䞭、䟋えば、キシレントル゚ン等の炭化氎玠
類、クロルベンれン、ゞクロルベンれン等のハロ
ゲン化炭化氎玠類䞭、還流条件䞋もしくは溶媒䞍
圚䞋に匏の化合物を加熱するこずにより行
なうこずができる。 かくしお埗られる匏の化合物はそれ自䜓
公知の手段、䟋えば、再結晶、抜出、クロマトグ
ラフむヌ等の手段により粟補するこずができる。 〔匏䞭、R1R2は前蚘の意味を有する〕 次に匏の脱氎反応は、溶媒の䞍圚䞋又は
䞍掻性溶媒䞭で、匏の化合物を脱氎剀で凊
理するこずにより行なうこずができる。 甚いうる䞍掻性溶媒ずしおは、䟋えばクロロホ
ルム四塩化炭玠などのハロゲン化炭化氎玠、ベン
れン、トル゚ン、キシレン等の芳銙族炭化氎玠が
適しおいる。 たた、匏の化合物の脱氎に䜿甚し埗る脱
氎剀ずしおは、五酞化リン、五塩化リン、オキシ
塩化リン等が有利に䜿甚され、これら脱氎剀の䜿
甚量は䞀般に匏の化合物モルに察しお少
なくずも圓量、奜たしくは〜10倍圓量の過剰量
で䜿甚するのが有利である。反応は䞀般に垞枩か
ら反応混合物の還流枩床においお、奜たしくは玄
50℃から反応混合物の還流枩床の範囲の昇枩条件
䞋に行うこずができ、必芁に応じお、ピリゞン、
トリ゚チルアミン、ゞメチルホルムアミド等の塩
基の存圚䞋に行なうこずができ、それによ぀お反
応を促進するこずができる。かかる塩基の䜿甚量
は通垞匏の化合物に察し数重量から倍
モルで䜿甚される。かかる条件䞋に䞊蚘脱氎反応
は通垞〜時間皋床で終了させるこずができ
る。 かくしお埗られる前蚘匏の化合物は、そ
れ自䜓公知の手段、䟋えば再結晶、抜出、クロマ
トグラフむヌ等の手段により、分離及び又は粟
補するこずができる。 次に参考䟋、実斜䟋を挙げお前蚘匏の化
合物の補造方法をされに具䜓的に説明する。 参考䟋  〔―カルバモむル――カルボキシ――
―プロピルアミノ―――クロルプニルピ
ラゞンの合成〕 ―ゞシアノ―――プロピルアミノ―
――クロルプニルピラゞン2.980.01モ
ルを芏定氎酞化ナトリりム60ml䞭に入れ窒玠
ガスを吹きこみながら100℃で時間撹拌し、埗
られた黄色溶液を芏定塩酞でPHに調敎した。
析出した結晶を集し、―ヘキサンで掗浄埌
2.3275収率の生成物を埗た。 融点196〜197℃分解。 元玠分析倀 C15H15N4O3Clずしお 蚈算倀 53.8  4.5  16.7 分析倀 54.0  4.3  16.9 参考䟋  〔―カルバモむル―――プロピルアミノ
―――クロルプニルピラゞンの合成〕 ―カルバモむル――カルボキシ―――
プロピルアミノ―――クロルプニルピラゞ
ン1.00.003モルをゞクロルベンれン10mläž­
にけんだくさせ175℃で時間撹拌した。反応埌
の赀か぀色溶液を冷蔵庫䞭に䞀倜攟眮し、析出物
を集し、氎掗埌0.15の生成物を埗た。 融点175〜177℃。 元玠分析倀 C14H15N4OClずしお 蚈算倀 57.8  5.2  19.3 実枬倀 57.7  5.5  19.5 実斜䟋  〔―シアノ―――プロピルアミノ――
―クロルプニルピルゞンの合成〕 ―カルバモむル―――プロピルアミノ―
――クロルプニルピラゞン1.00.0034
モルをオキシ塩化リン21.10.138モル䞭
に入れ、〜℃でピリゞン0.550.0069モ
ルを添加し、45分間撹拌埌、時間還流した。
反応埌濃瞮し、残留物をクロロホルム60mlに溶解
し、氎掗埌クロロホルム溶液を濃瞮し、埗られた
赀色油状物に―ヘキサンを添加し、析出物を
集埌、―ヘキサンから再結晶しお0.55の生成
物を埗た。融点83〜84℃。 元玠分析倀 C14H13N4Clずしお 蚈算倀 61.7  4.8  20.5 実枬倀 62.0  5.0  20.4 IRKBr法、極倧吞収cm-1 336022151560。 実斜䟋 〜 実斜䟋に蚘茉したず同様の方法により䞋蚘第
衚に蚘茉の化合物を埗た。
The present invention relates to a novel pyrazine derivative, and more particularly to a 2-cyanopyrazine derivative and a herbicide containing the compound as an active ingredient. According to the invention, the general formula [In the formula, R 1 represents an ethyl group or n-propyl group, and R 2 represents a hydrogen atom, a halogen atom, or a methyl group] A 2-cyanopyrazine derivative represented by the following is provided. A group of 2-cyanopyrazine derivatives represented by the formula () are new compounds that have not been described in any literature, and the present inventors have now discovered that these compounds have excellent herbicidal activity as active ingredients of herbicides. It was done. In particular, in paddy field flooded soil treatment and upland soil treatment, the compound of formula () forms a firm chemical treatment layer on the soil surface, is virtually harmless to transplanted rice, and is effective against annual weeds such as field weeds. It was found that it has excellent control ability. Examples of the "halogen atom" used in the general formula () include fluorine, chlorine, sulfur, and iodine, with fluorine or chlorine being preferred. The 2-cyanopyrazine derivative of the present invention is, for example, a compound 2,3-dicyanopyrazine derivative (Japanese Patent Application Laid-Open No. 1983-1990), which is a compound known per se and represented by the following formula ().
106479, JP-A-55-45634) as a starting material, it is produced by hydrolysis reaction, decarboxylation reaction, and dehydration reaction. [In the formula, R 1 and R 2 have the above-mentioned meanings] In the hydrolysis reaction of the compound of the above formula (), an alkali metal hydroxide or an alkaline earth metal carbonate is mixed with water and/or an alcohol such as methanol or ethanol. This can be done by acting in a similar environment. Generally, -CN group becomes -CONH 2 group by hydrolysis, but -CONH 2 group undergoes further hydrolysis to -CONH 2 group.
Easily generates COOH groups. Therefore, by hydrolyzing the -CN group, one becomes -CONH 2 group and the other becomes -COOH
In order to hydrolyze these groups, it is necessary to carefully select the reaction conditions, and the alkali metal hydroxides or alkaline earth metal carbonates used include sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, and potassium carbonate. can give you
Among them, sodium hydroxide is preferred, and the amount used is generally from 1 mol to 1 mol of the compound of formula ().
Advantageously, 1.5 mol is used. The above hydrolysis reaction can be carried out from room temperature to the reflux temperature of the reaction mixture, preferably at reflux temperature, for a reaction time of usually 1 to 3 hours. The compound of formula () thus obtained can be purified by means known per se, such as recrystallization, extraction or chromatography. [In the formula, R 1 and R 2 have the above-mentioned meanings] Next, the decarboxylation reaction of the compound of formula () is carried out using a hydrocarbon such as xylene toluene, chlorobenzene, dichlorobenzene, etc. in an inert solvent. This can be carried out by heating a compound of formula () in a halogenated hydrocarbon such as under reflux conditions or in the absence of a solvent. The compound of formula () thus obtained can be purified by means known per se, such as recrystallization, extraction, chromatography, etc. [In the formula, R 1 and R 2 have the above-mentioned meanings] Next, the dehydration reaction of formula () is carried out by treating the compound of formula () with a dehydrating agent in the absence of a solvent or in an inert solvent. can be done. Suitable inert solvents that can be used include, for example, halogenated hydrocarbons such as chloroform carbon tetrachloride, and aromatic hydrocarbons such as benzene, toluene, and xylene. Further, as a dehydrating agent that can be used for dehydrating the compound of formula (), phosphorus pentoxide, phosphorus pentachloride, phosphorus oxychloride, etc. are advantageously used, and the amount of these dehydrating agents used is generally determined for the compound 1 of formula (). It is advantageous to use a molar excess of at least equivalents, preferably 3 to 10 equivalents. The reaction is generally carried out at room temperature to the reflux temperature of the reaction mixture, preferably at about
It can be carried out under elevated temperature conditions ranging from 50 °C to the reflux temperature of the reaction mixture, and if necessary, pyridine,
The reaction can be carried out in the presence of a base such as triethylamine or dimethylformamide, thereby promoting the reaction. The amount of such a base to be used is usually from several % by weight to twice the molar amount of the compound of formula (). Under such conditions, the dehydration reaction can usually be completed in about 2 to 5 hours. The compound of formula () thus obtained can be separated and/or purified by means known per se, such as recrystallization, extraction, chromatography, etc. Next, the method for producing the compound of formula () will be specifically explained with reference to reference examples and examples. Reference example 1 [2-carbamoyl-3-carboxy-5-n
-Synthesis of propylamino-6-m-chlorophenylpyrazine] 2,3-dicyano-5-n-propylamino-
2.98 g (0.01 mol) of 6-m-chlorophenylpyrazine was placed in 60 ml of 1N sodium hydroxide, stirred at 100°C for 3 hours while blowing nitrogen gas, and the resulting yellow solution was adjusted to pH 2 with 6N hydrochloric acid. It was adjusted.
Collect the precipitated crystals and wash with n-hexane.
2.32 g (75% yield) of product was obtained. Melting point 196-197°C (decomposition). Elemental analysis value C 15 H 15 N 4 O 3 Calculated value as Cl: C 53.8 H 4.5 N 16.7 Analysis value: C 54.0 H 4.3 N 16.9 Reference example 2 [2-carbamoyl-5-n-propylamino-6-m- Synthesis of chlorphenylpyrazine] 2-carbamoyl-3-carboxy-5-n-
1.0 g (0.003 mol) of propylamino-6-m-chlorophenylpyrazine was suspended in 10 ml of dichlorobenzene and stirred at 175°C for 1 hour. After the reaction, the red colored solution was left in a refrigerator overnight, and the precipitate was collected, and after washing with water, 0.15 g of product was obtained. Melting point 175-177℃. Elemental analysis value C 14 H 15 N 4 Calculated value as OCl: C 57.8 H 5.2 N 19.3 Actual value: C 57.7 H 5.5 N 19.5 Example 1 [2-cyano-5-n-propylamino-6-
Synthesis of m-chlorphenylpyrudine] 2-carbamoyl-5-n-propylamino-
6-m-chlorophenylpyrazine 1.0g (0.0034
mol) was placed in 21.1 g (0.138 mol) of phosphorus oxychloride, 0.55 g (0.0069 mol) of pyridine was added at 3 to 4°C, stirred for 45 minutes, and then refluxed for 4 hours.
After the reaction, concentrate, dissolve the residue in 60 ml of chloroform, wash with water, concentrate the chloroform solution, add n-hexane to the resulting red oil, collect the precipitate, and recrystallize from n-hexane. 0.55g of product was obtained. Melting point 83-84℃. Elemental analysis value as C 14 H 13 N 4 Cl Calculated value: C 61.7 H 4.8 N 20.5 Actual value: C 62.0 H 5.0 N 20.4 IR (KBr method, maximum absorption cm -1 ) 3360, 2215, 1560. Examples 2-5 The compounds listed in Table 1 below were obtained by the same method as described in Example 1.

【衚】【table】

【衚】 本発明により提䟛される匏で瀺される
―シアノピラゞン誘導䜓は、前述したずおり、氎
田湛氎土壌凊理、雑草生育期茎葉凊理、畑地土壌
凊理等においお非垞に優れた遞択的陀草掻性を瀺
し、陀草剀の有効成分ずしお極めお適しおいる。 かくしお、本発明によれば、匏で瀺され
る―シアノピラゞン誘導䜓を有効成分ずする陀
草剀が提䟛される。 本発明の陀草剀は雑草の皮子の発芜を抑制し及
び又は雑草の茎葉を枯死させる胜力を有し、発
芜前陀草剀及び又は発芜埌陀草剀ずしお、氎田
湛氎土壌凊理、雑草生育期茎葉凊理、畑地土壌凊
理等においおすぐれた陀草効果を発揮するもので
ある。特に、本発明の陀草剀は氎を豊富に湛えら
れる湛氎田においお優れた陀草掻性を発珟し、氎
田甚陀草剀ずしお有利に䜿甚するこずができる。
これは本発明の掻性化合物が氎に溶解しお雑草の
皮子、根や氎䞭の茎葉から容易に吞収され、該雑
草の発芜阻止、生育阻害、枯死等に盎接䜜甚する
からであるず考えられる。 本発明の化合物を有効成分ずする陀草剀は土壌
の衚局から発芜する雑草を遞択的に癜化枯死せし
める効果を有し、たた、これを畑地で茎葉凊理に
䜿甚した堎合においおも、むネ等の重芁経枈䜜物
に察しお実質的に無害でか぀むネ等の栜培地に発
生する陀草を遞択的に癜化防陀するこずができ
る。 本発明の陀草剀によ぀お防陀するこずのできる
陀草ずしおは、䟋えば䞋蚘のものを䟋瀺するこず
ができるが、䞋蚘の列挙は単なる䟋瀺であり、本
発明の陀草剀はその他の雑草に察しおも同様に優
れた陀草効果を発揮するこずを理解すべきであ
る。 (1) 氎田雑草ずしお、䟋えばキク科䟋タりコ
ギ、ゎマノハグ科䟋サワトりガラシ、ア
ブノメ、アれトりガラシ、アれナ、ミ゜ハギ
科䟋ヒメミ゜ハギ、キカシグサ、ミ゜ハ
ギ、ミゟハコベ科䟋ミゟハコベ、アワゎ
ケ科、䟋ミズハコベ、アカバナ科䟋チ
ペりゞタデ、タデ科䟋ダナギタデ、ミズ
アオむ科䟋コナギ、ホシクサ科䟋ホ
シクサ、むヌノヒゲ、りキクサ科䟋りキ
クサ、ヒンゞモ、アオりキクサ、カダツリグ
サ科䟋ヒデリコ、ホタルむ、タマガマツ
リ、マツバむ、むネ科䟋ハむヌメリ、ノ
ビ゚、トチカガミ科䟋スブタ、ミズオオ
バコ、オモダカ科䟋ヘラオモダカ、テン
ゞ゜り科䟋テンゞ゜り、ホシミドロ科
䟋アむミドロ、など。 (2) 畑地雑草ずしお、䟋えばアカザ科䟋コア
カザ、アブラナ科䟋ナズナ、ノダむコ
ン、野生カラシナ、ヒナ科䟋アオビナ、
タデ科䟋ギシキシ、ハルタデ、アカネ科
䟋ダ゚ムグラ、ナデシコ科䟋ミミナグ
サ、ノミノフスマ、コハコベ、ゎマノハグサ
科䟋むヌノフグリ、キク科䟋ハルゞ
ペン、ヒメムカシペモギ、セむペりタンポ
ポ、ヒルガオ科䟋コヒルガオ、カタバミ
科䟋カタバミ、むネ科䟋スズメノテ
ツポり、スズメノカタビラ、メヒシバ、トり
ダむグサ科䟋コニシキ゜り、ナス科
䟋むヌホりズキ、カダツリグサ科䟋コ
ゎメガダツリなど。 本発明の化合物を陀草剀の有効成分ずしお䜿甚
する堎合には、前蚘匏で瀺される掻性化合
物の皮又は皮以䞊の組合せを、陀草剀分野に
おいお通垞䜿甚される䞍掻性な液䜓又は固䜓の担
䜓材料又は垌釈剀及び必芁に応じお、界面掻性剀
などの添加物ず混合し、適圓な剀圢に補剀するこ
ずができる。 本発明の陀草剀にもちいうる担䜓材料たたは垌
釈剀ずしおは、圓該分野においお通垞䜿甚されお
いるものはいずれも䜿甚でき、固䜓の担䜓材料た
たは垌釈剀ずしおは、䟋えばカオリン、ケむ゜り
土、タルク、ベントナむト、モンモリロナむト、
シリカ、クレヌ、バヌミキナラむト、ホワむトカ
ヌボン、雲母、石こう、炭酞カルシりム、でん
粉、怍物粉などが挙げられ、たた液䜓の担䜓材料
たたは垌釈剀ずしおは、䟋えば氎、゚タノヌル、
シクロヘキサン、キシレン、トル゚ン、ベンれ
ン、メチルナフタレン、ケロシン、アセトン、メ
チル゚ナルケトン、シクロヘキサノン、む゜ホロ
ン、―ゞメチルホルムアミド、ゞメチルス
ルホキシド、テトラヒドロフラン、ゞオキサン、
゚チレングリコヌル゚チル゚ヌテル、液化したテ
トラフルオロ゚タンなどが挙げられる。 本発明の陀草剀はその剀圢に応じお界面掻性剀
を通垞の量で含むこずができ、かかる界面掻性剀
の䟋ずしおは、䟋えばアルキルベンれンスルホン
酞塩、リグニンスルホン酞塩、ナフタリンスルホ
ン酞塩ホルマリン瞮合物、ゞアルキルスルホコハ
ク酞゚ステル゜ヌダ塩、脂肪酞塩、アルキル硫酞
塩、高玚アルコヌル硫酞゚ステル、゜ルビタン脂
肪酞゚ステル、ポリアルキレングリコヌル、ポリ
オキシアルキレンモノアルキル゚ヌテル、ポリオ
キシアルキレンアルキルアリヌル゚ヌテル、ポリ
オキシアルキレン脂肪酞゚ステル、ポリオキシア
ルキレンアルキルメルカブタン゚ヌテル、第玚
アンモニりム塩などを単独でたたは皮以䞊組合
せお䜿甚するこずができる。 しかしお、本発明の陀草剀は、その剀圢にもよ
るが、䞀般には、前蚘匏の掻性化合物を、
陀草剀の重量を基準にしお、少なくずも0.5重量
、奜たしくは〜99重量、さらに奜適には
〜80重量の濃床で含むこずができる。 たた、本発明の陀草剀は、その斜甚方法に応じ
お、粉剀、粒剀、氎和剀、溶剀、乳剀、噎霧剀等
の通垞の任意の剀圢に補剀される。その補剀は圓
該分野でそれ自䜓公知の方法により行なうこずが
できる。䟋えば、粉剀、粒剀および氎和剀は、匏
の掻性化合物の少なくずも皮を䞊蚘の固
䜓の担䜓材料たたは垌釈剀の少なくずも皮ず共
に混合粉砕し、適量の界面掻性剀を添加し、均䞀
に混合しお補剀化するこずができる。たた、溶液
たたは乳剀は匏の掻性化合物の少なくずも
皮を䞊蚘の液䜓の担䜓材料たたは垌釈剀の少な
くずも皮䞭に溶解ないし分散させ、さらに必芁
に応じお界面掻性剀を加えるこずにより補剀化し
埗る。 かくしお、陀草剀の重量を基準にしお、粉剀お
よび粒剀の堎合には、掻性化合物を〜80重量
の濃床で、氎和剀、溶液および乳剀の堎合には
〜60重量の濃床で含たせるこずができる。 さらに、本発明の陀草剀は、蟲業分野で通垞䜿
甚される殺菌剀、殺虫剀、殺線虫剀、肥料、怍物
生長調節剀等を含むこずができ、たた他の陀草剀
ず䜵甚するこずもできる。 前述したように、本発明の陀草剀は、発芜前お
よびたたは発芜埌の陀草剀ずしお、氎田湛氎土
壌凊理たたは畑地土壌凊理ずしお盎媒土壌に斜甚
するか、あるいは茎葉凊理ずしお雑草に盎接散垃
するこずができる。その堎合の斜甚量は臚界的な
ものではなく、掻性化合物の皮類、斜甚時期、斜
甚方法等に応じお広範に倉えるこずができるが、
䞀般に10アヌル圓り少なくずも、25、奜たしく
は50〜2000の掻性化合物ずなるように斜甚する
のが有利である。しかし䞊蚘斜甚量は䞀応の基準
であり、䜜物の状態、雑草のはびこり状態等に応
じお、䞊蚘量よりも少なくたたは倚く甚いるこず
も勿論可胜である。 たた、その斜甚方法ずしおは、通垞の任意の方
法を䜿甚するこずずができ、䟋えば䜜物の播皮た
たは移怍前たたは埌に防陀すべき地域に地䞊たた
は空䞭から散垃する方法、䜜物の播皮時に皮子ず
䞀緒に散垃する方法等が甚いられる。あるいはた
た、䜜物の皮子の播皮の前で、䜜物の皮子を本発
明の掻性化合物を含む氎溶液䞭に浞挬凊理するこ
ずにより、䜜物の皮子䞭に混入しおいる雑草の皮
子の発芜を抑制するこずも可胜である。 次に本発明により提䟛される陀草剀の補剀の具
䜓䟋および陀草掻性を以䞋の補剀䟋によりさらに
説明する。補剀䟋䞭「郚」は重量郚である。 補剀䟋 氎和剀 本発明の掻性化合物40郚を、担䜓材料ずしおゞ
ヌクラむト〔商品名ゞヌクラむト化孊瀊業(æ ª)
補〕ずクニラむト〔商品名クニミネ工業(æ ª)補〕
ずの混合物55郚および界面掻性剀ずしお゜
ルボヌル800A〔商品名東邊化孊工業(æ ª)補〕
郚ず共に混合粉砕しお40氎和剀を埗る。 補剀䟋 乳剀 本発明の掻性化合物15郚、テトラヒドロフラン
80郚および界面掻性剀゜ルボヌル800A郚
を混合溶解しお15乳剀を埗る。 補剀䟋 粒剀 本発明の掻性化合物10郚、ベントナむト50郚、
クニラむト35郚および界面掻性剀゜ルボヌル
800A郚を混合粉砕したのち、氎10郚を加え
お均䞀に撹拌し、盎埄0.7mmの篩穎から抌し出し
お也燥埌、適圓な長さに切断しお10粒剀を埗
る。 次に本発明に係る陀草剀の怍物詊隓結果を瀺
し、本発明の䜿甚法およびその効果を明らかにす
る。 詊隓䟋 氎田湛氎土壌凊理方法 1/5000アヌルのポリ゚チレン補ポツトに氎田土
壌怍壌土を充おんし、ノビ゚、広葉雑草、ホ
タルむの各皮子を衚局cmに播皮し、マツバむ
株を移怍した。同時に氎皲葉期を本株怍え
ずし、cmの深さに移怍しおcmに湛氎した。 雑草発芜ず同時に本発明の掻性化合物を含む氎
和剀の所定量を秀量し、ポツト圓り10mlの氎に
垌釈し氎面に滎䞋凊理した。その埌ガラス宀にお
いお育成し、凊理週間埌に陀草効果および氎皲
におよがす圱響を調査した。結果は䞋蚘第衚に
瀺す通りである。なお、詊隓䟋における衚䞭の数
倀は氎皲薬害および陀草効果の皋床を瀺すもので
具䜓的には䞋蚘の通りである。
[Table] 2 represented by the formula () provided by the present invention
- As mentioned above, cyanopyrazine derivatives exhibit very excellent selective herbicidal activity in the treatment of flooded paddy soil, foliage treatment during the weed growing season, field soil treatment, etc., and are extremely suitable as active ingredients in herbicides. Thus, according to the present invention, a herbicide containing a 2-cyanopyrazine derivative represented by the formula () as an active ingredient is provided. The herbicide of the present invention has the ability to suppress the germination of weed seeds and/or kill the foliage of weeds, and can be used as a pre-emergence herbicide and/or a post-emergence herbicide in paddy field flooding soil treatment, during the weed growth period. It exhibits excellent herbicidal effects in foliage treatment, field soil treatment, etc. In particular, the herbicide of the present invention exhibits excellent herbicidal activity in flooded paddy fields that are rich in water, and can be advantageously used as a herbicide for paddy fields.
This is thought to be because the active compound of the present invention dissolves in water and is easily absorbed from the seeds, roots, and leaves of weeds in water, and directly acts on the germination inhibition, growth inhibition, withering, etc. of the weeds. The herbicide containing the compound of the present invention as an active ingredient has the effect of selectively bleaching and killing weeds that germinate from the surface layer of the soil. It is substantially harmless to economic crops and can selectively control bleaching of weeds that occur in cultivated areas such as rice. Examples of weeds that can be controlled by the herbicide of the present invention include the following, but the following list is merely an example, and the herbicide of the present invention is effective against other weeds. It should be understood that it also exhibits excellent herbicidal effects as well. (1) Examples of rice field weeds include Asteraceae (e.g., Asteraceae), Lythraceae (e.g., Siberian capsicum, Aphrodisia spp., Azetian capsicum, Azeena), Lythraceae (e.g., Lythrum japonica, Lythrum japonica, Lythrum), Lythraceae (e.g. Lythrum japonica) , Polygonaceae, (e.g., water chickweed), Polygonaceae (e.g., Polygonaceae), Polygonaceae (e.g., willow knotweed), Chrysophyllaceae (e.g., Coccinaceae), Asteraceae (e.g., Asteraceae, Cannabis), Lemnaceae (e.g., Duckweed) , Hinjimo, Lemna), Cyperaceae (e.g., Hyderico, Firefly, Lamina, Cyperaceae), Poaceae (e.g., Poaceae, Noviaceae), Cyperaceae (e.g., Sagittarius, Lemna), Cyperaceae (e.g., Helaomodacaceae), Adifoliaceae (e.g. Adifoliaceae), Porphyridaceae (e.g. Aimidoro), etc. (2) Upland weeds include, for example, Chenopodiaceae (e.g., Coaxiaceae), Brassicaceae (e.g., shepherd's purse, Japanese radish, wild mustard), Amaranthaceae (e.g., Amaranthaceae),
Polygonaceae (e.g., Physcomyceae), Rubiaceae (e.g., Caryophyllaceae), Caryophyllaceae (e.g., Pygmyensis, Psyllidaceae, Caryophyllaceae), Psyllidaceae (e.g., Pyropianum), Asteraceae (e.g., P. elegans, Artemisia elegans, Dandelion), Convolvulaceae (e.g. Convolvulaceae), Oxalis (e.g. Oxalis), Poaceae (e.g. Poaceae, Poaceae), Euphorbiaceae (e.g. Convolvulus), Solanaceae (e.g. Cyperaceae), Cyperaceae (e.g. Cyperaceae) )Such. When the compound of the present invention is used as an active ingredient of a herbicide, one or a combination of two or more of the active compounds represented by the above formula () may be used in an inert liquid or an inert liquid commonly used in the herbicide field. It can be mixed with a solid carrier material or diluent and, if necessary, additives such as a surfactant, and formulated into a suitable dosage form. As the carrier material or diluent that can be used in the herbicide of the present invention, any carrier material or diluent commonly used in the field can be used. Examples of the solid carrier material or diluent include kaolin, diatomaceous earth, talc, and bentonite. , montmorillonite,
Examples include silica, clay, vermiculite, white carbon, mica, gypsum, calcium carbonate, starch, vegetable flour, etc., and liquid carrier materials or diluents include, for example, water, ethanol,
Cyclohexane, xylene, toluene, benzene, methylnaphthalene, kerosene, acetone, methylenalketone, cyclohexanone, isophorone, N,N-dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, dioxane,
Examples include ethylene glycol ethyl ether and liquefied tetrafluoroethane. The herbicide of the present invention may contain a surfactant in a conventional amount depending on its dosage form, and examples of such surfactants include, for example, alkylbenzene sulfonate, lignin sulfonate, naphthalene sulfonate, formalin Condensate, dialkyl sulfosuccinate sodium salt, fatty acid salt, alkyl sulfate, higher alcohol sulfate ester, sorbitan fatty acid ester, polyalkylene glycol, polyoxyalkylene monoalkyl ether, polyoxyalkylene alkylaryl ether, polyoxyalkylene fatty acid ester, Polyoxyalkylene alkylmerkabutane ether, quaternary ammonium salts, and the like can be used alone or in combination of two or more. Therefore, the herbicide of the present invention generally contains the active compound of the formula (), although it depends on its dosage form.
At least 0.5% by weight, preferably 1 to 99%, more preferably 2% by weight, based on the weight of the herbicide.
It can be included in concentrations of ~80% by weight. Furthermore, the herbicide of the present invention can be formulated into any conventional dosage form such as a powder, granule, wettable powder, solvent, emulsion, or spray, depending on the method of application. The formulation can be carried out by methods known per se in the art. For example, powders, granules and wettable powders can be prepared by mixing and grinding at least one active compound of formula () with at least one of the solid carrier materials or diluents mentioned above, adding an appropriate amount of surfactant; They can be mixed uniformly and formulated into a formulation. Solutions or emulsions can also be prepared by dissolving or dispersing at least one active compound of formula () in at least one of the above liquid carrier materials or diluents, and optionally adding a surfactant. can be converted into Thus, in the case of powders and granules, from 2 to 80% by weight of active compound, based on the weight of the herbicide.
5 for wettable powders, solutions and emulsions.
It can be included at a concentration of ~60% by weight. Furthermore, the herbicide of the present invention can contain fungicides, insecticides, nematicides, fertilizers, plant growth regulators, etc. commonly used in the agricultural field, and can also be used in combination with other herbicides. can. As mentioned above, the herbicide of the present invention can be applied as a pre-emergence and/or post-emergence herbicide to direct soil as a paddy field flooded soil treatment or upland soil treatment, or directly sprayed on weeds as a foliar treatment. can do. The amount applied is not critical and can vary widely depending on the type of active compound, time of application, method of application, etc.
It is generally advantageous to apply at least 25 g, preferably from 50 to 2000 g of active compound per 10 are. However, the above application amount is just a standard, and it is of course possible to use less or more than the above amount depending on the condition of the crop, the infestation of weeds, etc. In addition, any conventional method can be used for its application, such as applying it from the ground or in the air to the area to be controlled before or after sowing or transplanting crops, or applying it together with seeds when sowing crops. Methods such as spraying on the ground are used. Alternatively, the germination of weed seeds contained in crop seeds can be inhibited by soaking the crop seeds in an aqueous solution containing the active compound of the present invention before sowing the crop seeds. is also possible. Next, specific examples of herbicide formulations and herbicidal activity provided by the present invention will be further explained using the following formulation examples. In the formulation examples, "parts" are parts by weight. Formulation Example 1 (Wettable powder) 40 parts of the active compound of the present invention was mixed with Zeeklite (trade name: Zeeklite Chemical Co., Ltd.) as a carrier material.
[manufactured by Kunimine Kogyo Co., Ltd.] and Kunilite [product name: manufactured by Kunimine Kogyo Co., Ltd.]
55 parts of a 2:1 mixture of
40% wettable powder is obtained. Formulation Example 2 (Emulsion) 15 parts of active compound of the invention, tetrahydrofuran
Mix and dissolve 80 parts and 5 parts of a surfactant (Sorbol 800A) to obtain a 15% emulsion. Formulation Example 3 (Granules) 10 parts of the active compound of the present invention, 50 parts of bentonite,
35 parts of Kunilite and surfactant (Solbol
After mixing and pulverizing 5 parts of 800A), add 10 parts of water, stir evenly, extrude through a sieve hole with a diameter of 0.7 mm, dry, and cut into appropriate lengths to obtain 10% granules. Next, plant test results of the herbicide according to the present invention will be shown to clarify the method of use of the present invention and its effects. Test Example 1 (Paddy field flooded soil treatment method) Fill a 1/5000 are polyethylene pot with paddy soil (planting soil), sow seeds of wild grass, broad-leaved weeds, and firefly to a surface layer of 2 cm.
The stock was transplanted. At the same time, two 3-leaf stage paddy rice plants were planted, transplanted to a depth of 2 cm, and flooded to a depth of 3 cm. At the same time as weed germination, a predetermined amount of a wettable powder containing the active compound of the present invention was weighed out, diluted to 10 ml of water per pot, and dropped onto the water surface. Thereafter, the plants were grown in a glass room, and three weeks after the treatment, the herbicidal effect and the effect on paddy rice were investigated. The results are shown in Table 2 below. In addition, the numerical values in the table in the test examples indicate the degree of paddy rice phytotoxicity and herbicidal effect, and are specifically as follows.

【衚】【table】

【衚】【table】

【衚】【table】

Claims (1)

【特蚱請求の範囲】  䞀般匏 〔匏䞭、R1ぱチル基もしくは―プロピル
基を衚わし、R2は氎玠原子、ハロゲン原子、た
たはメチル基を衚わす〕 で瀺される―シアノピラゞン誘導䜓。  䞀般匏 〔匏䞭、R1ぱチル基もしくは―プロピル
基を衚わし、R2は氎玠原子、ハロゲン原子、た
たはメチル基を衚わす〕 で瀺される―シアノピラゞン誘導䜓を有効成分
ずする陀草剀。
[Claims] 1. General formula [In the formula, R 1 represents an ethyl group or n-propyl group, and R 2 represents a hydrogen atom, a halogen atom, or a methyl group] A 2-cyanopyrazine derivative represented by the following formula. 2 General formula [In the formula, R 1 represents an ethyl group or n-propyl group, and R 2 represents a hydrogen atom, a halogen atom, or a methyl group] A herbicide containing a 2-cyanopyrazine derivative as an active ingredient.
JP11324380A 1980-08-18 1980-08-18 Novel cyanopyrazine derivative Granted JPS5738778A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP11324380A JPS5738778A (en) 1980-08-18 1980-08-18 Novel cyanopyrazine derivative

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP11324380A JPS5738778A (en) 1980-08-18 1980-08-18 Novel cyanopyrazine derivative

Publications (2)

Publication Number Publication Date
JPS5738778A JPS5738778A (en) 1982-03-03
JPS6241592B2 true JPS6241592B2 (en) 1987-09-03

Family

ID=14607189

Family Applications (1)

Application Number Title Priority Date Filing Date
JP11324380A Granted JPS5738778A (en) 1980-08-18 1980-08-18 Novel cyanopyrazine derivative

Country Status (1)

Country Link
JP (1) JPS5738778A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101114704B1 (en) * 2006-10-04 2012-03-14 에프. 혾프만-띌 로슈 아게 Pyrazine-2-carboxamide derivatives as cb2 receptor modulators

Also Published As

Publication number Publication date
JPS5738778A (en) 1982-03-03

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