JP2639428B2 - Substituted thenylsulfonamide derivatives, their preparation and selective herbicides - Google Patents
Substituted thenylsulfonamide derivatives, their preparation and selective herbicidesInfo
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- JP2639428B2 JP2639428B2 JP1987788A JP1987788A JP2639428B2 JP 2639428 B2 JP2639428 B2 JP 2639428B2 JP 1987788 A JP1987788 A JP 1987788A JP 1987788 A JP1987788 A JP 1987788A JP 2639428 B2 JP2639428 B2 JP 2639428B2
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- lower alkyl
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Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は一般式〔Ｉ〕 （式中Ｘ及びＹは互いに独立してハロゲン原子、低級ア
ルキル基またはハロアルキル基を示し、ｎは０、１、
２、ｍは０、１を示し、Ｒは低級アルキル基、低級アル
コキシアルキル基、ハロアルキル基、低級アルケニル基
または低級アルキニル基を示し、R1は−CONH2、−CSN
H2、−CNまたは−CONH−R2を示し、R2はアルコキシカル
ボニル基またはアルキルカルボニル基を示す。） で表わされる置換テニルスルホンアミド誘導体（以下、
本発明化合物という）、その製造法及び該化合物を有効
成分として含有する選択性除草剤に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a compound represented by the general formula [I]: (Wherein X and Y independently represent a halogen atom, a lower alkyl group or a haloalkyl group, and n is 0, 1,
2, m indicates 0, 1, R represents a lower alkyl group, a lower alkoxyalkyl group, a haloalkyl group, a lower alkenyl group or a lower alkynyl group, R 1 is -CONH 2, -CSN
H 2 represents —CN or —CONH—R 2 , and R 2 represents an alkoxycarbonyl group or an alkylcarbonyl group. The substituted phenylsulfonamide derivative represented by
The present invention relates to a compound of the present invention, a method for producing the compound and a selective herbicide containing the compound as an active ingredient.
農作物を雑草害から守り増収をはかるため、各種系統
の化合物が研究され、多種類の除草剤が実用場面で使用
され、農業の生産性を高める上で多大の貢献をしている
ことは知られている。しかしながら、これら除草剤の大
部分は稲作、とくに直播栽培方式において強害雑草であ
るヒエ類に対して強力な活性と同時に稲に対して高度の
安全性を示すいわゆる稲−ヒエ層間選択性を有するもの
ではない。In order to protect crops from weed damage and increase yield, it is known that various strains of compounds have been studied, and many kinds of herbicides are used in practical situations, and that they have made a great contribution to increasing agricultural productivity. ing. However, most of these herbicides have so-called rice-millet layer selectivity, which shows high safety against rice and at the same time has strong activity against rice, especially the direct-seeding cultivation system, which is a highly damaging weed. Not something.
或る種のスルホンアミド系化合物が稲−ヒエ属間選択
性を有することは知られている（特開昭53−44543号；
特開昭53−145916号）。しかしながら、その殺草活性は
満足すべきものではない。It is known that certain sulfonamide compounds have selectivity between the genus Rice and Japanese millet (JP-A-53-44543;
JP-A-53-145916). However, its herbicidal activity is not satisfactory.
本発明は水田稲作、とくに省力、低コスト型の近代的
農業形式である直播栽培において稲−ヒエ属間選択性、
ヒエ類に対する殺草活性、またはその効果的使用期間な
どの諸問題を同時に解決する新規な除草剤を提供するこ
とを目的とる。The present invention relates to rice-paddy rice cultivation, in particular, direct seeding cultivation, which is a modern labor-saving, low-cost type of agricultural system.
An object of the present invention is to provide a novel herbicide which simultaneously solves various problems such as herbicidal activity against barnyardgrass or its effective use period.
本発明者等は以上の諸問題を解決する有用な除草剤の
開発を目的として、特にスルホンアミド系化合物につい
て鋭意研究を重ねた結果、本発明化合物が稲−ヒエ属間
選択性、ヒエ殺草活性及び使用適期幅等に満足すべき特
性を有する事を見出し、本発明を完成するに至った。The present inventors have conducted intensive studies particularly on sulfonamide compounds with the aim of developing useful herbicides that solve the above-mentioned problems. The present inventors have found that they have satisfactory properties such as activity and suitable period of use, and have completed the present invention.
すなわち、本発明は （１） 一般式〔Ｉ〕 （式中Ｘ及びＹは互いに独立してハロゲン原子、低級ア
ルキル基またはハロアルキル基を示し、ｎは０、１、
２、ｍは０、１を示し、Ｒは低級アルキル基、低級アル
コキシアルキル基、ハロアルキル基、低級アルケニル基
または低級アルキニル基を示し、R1は−CONH2、−CSN
H2、−CNまたは−CONH−R2を示し、R2はアルコキシカル
ボニル基またはアルキルカルボニル基を示す。） で表わされる置換テニルスルホンアミド誘導体。That is, the present invention relates to (1) the general formula [I] (Wherein X and Y independently represent a halogen atom, a lower alkyl group or a haloalkyl group, and n is 0, 1,
2, m indicates 0, 1, R represents a lower alkyl group, a lower alkoxyalkyl group, a haloalkyl group, a lower alkenyl group or a lower alkynyl group, R 1 is -CONH 2, -CSN
H 2 represents —CN or —CONH—R 2 , and R 2 represents an alkoxycarbonyl group or an alkylcarbonyl group. ) A substituted thenylsulfonamide derivative represented by the formula:
（２） 一般式〔II〕 （式中Ｘ及びＹは互いに独立してハロゲン原子、低級ア
ルキル基またはハロアルキル基を示し、ｎは０、１、
２、ｍは０、１を示し、Ｚはハロゲン原子を示す。） で表わされる置換テニルスルホニルハライドと 一般式〔III〕 （式中Ｒは低級アルキル基、低級アルコキシアルキル
基、ハロアルキル基、低級アルケニル基または低級アル
キニル基を示し、R1は−CONH2、−CSNH2、−CNまたは−
CONH−R2を示し、R2はアルコキシカルボニル基またはア
ルキルカルボニル基を示す。） で表わされる化合物を反応させることを特徴とする 一般式〔Ｉ〕 （式中Ｘ、Ｙ、ｎ、ｍ、Ｒ、R1は前記と同じ意味を示
す。） で表わされる置換テニルスルホンアミド誘導体の製造方
法。(2) General formula [II] (Wherein X and Y independently represent a halogen atom, a lower alkyl group or a haloalkyl group, and n is 0, 1,
2, m represents 0 and 1, and Z represents a halogen atom. ) And a substituted thenylsulfonyl halide represented by the general formula [III] (Wherein R represents a lower alkyl group, a lower alkoxyalkyl group, a haloalkyl group, a lower alkenyl group or a lower alkynyl group, and R 1 represents —CONH 2 , —CSNH 2 , —CN, or —
It indicates CONH-R 2, R 2 represents an alkoxycarbonyl group or an alkylcarbonyl group. Wherein the compound represented by the general formula [I] is reacted: (Wherein X, Y, n, m, R, and R 1 have the same meanings as described above).
（３） 一般式〔Ｉ〕 （式中、Ｘ、Ｙ、ｎ、ｍ、Ｒ、R1は前記と同じ意味を示
す。） で表わされる置換テニルスルホンアミド誘導体を有効成
分として含有することを特徴とする選択性除草剤を提供
する。(3) General formula [I] (Wherein, X, Y, n, m, R, and R 1 have the same meanings as described above.) A selective herbicide characterized by containing a substituted phenylsulfonamide derivative represented by the following formula: I do.
本発明化合物は本発明者等が始めて合成した文献未記
載の新規化合物である。The compound of the present invention is a novel compound synthesized by the present inventors for the first time and not described in the literature.
本発明化合物は後記試験例に示される様に直播の稲に
対しても完全に安全である高度な稲−ヒエ属間選択性を
有し、強力なヒエ殺草活性更に発芽期及び生育の進んだ
ヒエに対しても完全に枯殺できる使用適期幅の広いすぐ
れた除草剤としての特性を有している。As shown in the test examples described below, the compound of the present invention has a high degree of selectivity between rice and genus, which is completely safe for direct-seeded rice, and has a strong herbicidal activity on the fly, and the germination stage and the growth are advanced. It has excellent herbicidal properties that can be completely killed even in barnyardgrass and that has a wide range of use.
本発明化合物は下記反応式で示される方法で合成する
ことができる。下記式のＸ、Ｙ、ｎ、ｍ、Ｚ、Ｒ、R1は
前記と同じ意味である。The compound of the present invention can be synthesized by a method represented by the following reaction formula. X, Y, n, m, Z, R and R 1 in the following formula have the same meanings as described above.
本発明化合物は、夫々の試薬の組合せで過剰の塩基性
物質の存在下に溶媒中で反応させることにより、容易に
得ることができる。 The compound of the present invention can be easily obtained by reacting each combination of the reagents in a solvent in the presence of an excess of a basic substance.
溶媒としてはアセトン等のケトン類、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、アルコール及び水等を単
独または混合して使用することができる。As the solvent, ketones such as acetone, ethers such as ether and tetrahydrofuran, acetonitrile, aromatic hydrocarbon, chlorinated hydrocarbon, alcohol, water and the like can be used alone or in combination.
塩基性物質としては、例えば炭酸カリウム、炭酸ナト
リウム、水酸化ナトリウム等の無機塩基並びにピリジ
ン、三級アミン等の有機塩基が使用され、通常過剰量が
使用されるが、好ましくは1.1〜３モル倍が適当であ
る。反応温度は−20℃から室温まで任意に設定できる
が、好ましくは−５゜〜10℃が適当である。スルホニル
ハライドとしてはスルホニルクロライドが適当であり、
当該アミンの使用量はスルホニルクロライドに対して過
剰が好ましく、通常1.1〜1.5モル倍が適当であり、また
脱酸剤をかねて２モル倍以上使用することもできる。第
一表に本発明の代表化合物を例示する。As the basic substance, for example, inorganic bases such as potassium carbonate, sodium carbonate and sodium hydroxide and organic bases such as pyridine and tertiary amine are used, and usually an excess amount is used, but preferably 1.1 to 3 times by mole. Is appropriate. The reaction temperature can be arbitrarily set from -20 ° C to room temperature, but preferably -5 ° C to 10 ° C. Sulfonyl chloride is suitable as the sulfonyl halide,
The amount of the amine to be used is preferably an excess with respect to the sulfonyl chloride, and is usually 1.1 to 1.5 times by mole, and the amine can be used in a molar amount of 2 times or more also as the deoxidizing agent. Table 1 shows representative compounds of the present invention.
次に、合成実施例をあげて本発明化合物の製造方法を
更に詳細に説明する。 Next, the production method of the compound of the present invention will be described in more detail with reference to Synthesis Examples.
〔実施例１〕 Ｎ−エチル−Ｎ−カルバモイルメチル−2,5−ジクロロ
−３−テニルスルホンアミドの合成 Ｎ′−エチルアミノアセトアミド2.24gのテトラヒド
ロフラン液30mlを０〜10℃に冷却し、撹拌下に2,5−ジ
クロロ−３−テニルスルホニルクロライド2.70gの10ml
テトラヒドロフラン液を滴下した。そのまま１時間撹拌
し、更に室温で１時間撹拌した後、氷冷水に注ぎ、油状
物をジクロロメタン抽出した。溶媒を留去し、得られた
粗製物をシリカゲルカラムクロマドグラフィーにより精
製して、融点113〜116℃の化合物番号１の目的物1.03g
を得た。Example 1 Synthesis of N-ethyl-N-carbamoylmethyl-2,5-dichloro-3-thenylsulfonamide 30 ml of a tetrahydrofuran solution of 2.24 g of N'-ethylaminoacetamide was cooled to 0 to 10 ° C., and stirred. 2.70 g of 2,5-dichloro-3-thenylsulfonyl chloride in 10 ml
Tetrahydrofuran solution was added dropwise. The mixture was stirred for 1 hour as it was and further for 1 hour at room temperature, then poured into ice-cold water, and the oil was extracted with dichloromethane. The solvent was distilled off, and the obtained crude product was purified by silica gel column chromatography to obtain 1.03 g of the desired product of Compound No. 1 having a melting point of 113 to 116 ° C.
I got
〔実施例２〕 Ｎ−エチル−Ｎ−カルバモイルメチル−2,5−ジブロモ
−３−テニルスルホンアミドの合成 Ｎ′−エチルアミノアセトアミド2.24gのテトラヒド
ロフラン20ml液を０〜10℃に冷却し、撹拌下に2,5−ジ
ブロモ−３−テニルスルホニルクロライド3.55gの10ml
テトラヒドロフラン液を滴下した。そのまま１時間撹拌
し、更に室温で１時間撹拌した後、氷冷水に注ぎ、油状
物をジクロロメタン抽出した。溶媒を留去し、得られた
粗製物をシリカゲルカラムクロマトグラフィーにより精
製して、融点156〜158℃の化合物番号４の目的物1.18g
を得た。Example 2 Synthesis of N-ethyl-N-carbamoylmethyl-2,5-dibromo-3-thenylsulfonamide A solution of 2.24 g of N'-ethylaminoacetamide in 20 ml of tetrahydrofuran was cooled to 0 to 10 ° C. and stirred. 2,5-dibromo-3-thenylsulfonyl chloride 3.55 g in 10 ml
Tetrahydrofuran solution was added dropwise. The mixture was stirred for 1 hour as it was and further for 1 hour at room temperature, then poured into ice-cold water, and the oil was extracted with dichloromethane. The solvent was distilled off, and the obtained crude product was purified by silica gel column chromatography to give 1.18 g of the desired product of Compound No. 4 having a melting point of 156 to 158 ° C.
I got
本発明化合物をそのまま使用してもよいが、一般に
は、乳剤、水和剤、粒剤、微粒剤、粉剤等に製剤して使
用することが有利である。Although the compound of the present invention may be used as it is, it is generally advantageous to use it by formulating it in an emulsion, wettable powder, granule, fine granule, powder or the like.
これら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、有機溶剤が
あげられるが、たとえばキシレン、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、たとえば
カオリン、タルク、ベントナイト、ケイソウ土、クレー
等があげられ、またアルミナ、ケイ酸塩等の合成化合物
も使用できる。製剤に当っては、乳化、分散、懸濁、浸
透等の特性を与えるため、各種の補助剤たとえば乳化
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。In preparing these formulations, liquid or solid carriers can be used. Examples of the liquid carrier include organic solvents. For example, xylene, chlorobenzene, methylnaphthalene, cyclohexanone, isophorone, alcohols, dimethylformamide, N-methylpyrrolidone and the like are advantageously used. Examples of the solid carrier include kaolin, talc, bentonite, diatomaceous earth, clay and the like, and synthetic compounds such as alumina and silicate can also be used. In the preparation, various auxiliaries such as an emulsifier, a dispersant, a spreading agent, a wetting agent, a penetrant and the like can be used in order to impart properties such as emulsification, dispersion, suspension and penetration.
また散布労力を低減する目的で、或いは有効に防除で
きる草種の幅を広げる目的で他の除草剤と混合して使用
することもできる。特に本発明化合物は広葉雑草には効
果が弱いことからこれらに有効な除草剤との混合は有意
義であり、実用場面では重要となる。It can also be used in combination with other herbicides for the purpose of reducing the labor for spraying or for expanding the range of grass species that can be effectively controlled. In particular, since the compound of the present invention has a weak effect on broadleaf weeds, its mixing with an effective herbicide is significant and important in practical use.
つぎに本発明化合物を有効成分として含有する除草剤
の製剤実施例及び殺草活性試験例を示すが、本発明は、
勿論これらのみに限定されるものではない。部は重量部
を示す。Next, Formulation Examples and herbicidal activity test examples of herbicides containing the compound of the present invention as an active ingredient are shown.
Of course, it is not limited only to these. Parts are parts by weight.
実施例３ 乳剤 化合物番号４の化合物20部にイソホロン15部、キシレ
ン60部を加え、これに乳化剤としてポリオキシエチレン
アルキルエーテル1.5部、アルキルベンゼンスルホネー
ト２部、ポリオキシエチレンソルビタンアルキレート1.
5部を加え、混合溶解して20％乳剤を得た。Example 3 Emulsion To 20 parts of the compound of Compound No. 4, 15 parts of isophorone and 60 parts of xylene were added, and 1.5 parts of polyoxyethylene alkyl ether, 2 parts of alkylbenzene sulfonate, and 1 part of polyoxyethylene sorbitan alkylate were added as emulsifiers.
Five parts were added and mixed and dissolved to obtain a 20% emulsion.
実施例４ 水和剤 化合物番号２の化合物30部にホワイトカーボン２部を
加えて混合し、これに分散湿展剤としてアルキルエーテ
ル硫酸ナトリウム３部及びジアルキルナフタレンスルホ
ン酸ナトリウム２部を加え、更に粉砕助剤としてクレー
63部を加え、全体をよく混合した後粉砕して30％水和剤
を得た。Example 4 Wettable powder 2 parts of white carbon was added to 30 parts of compound No. 2 and mixed, and 3 parts of sodium alkyl ether sulfate and 2 parts of sodium dialkylnaphthalenesulfonate were added as a dispersing and wetting agent, followed by pulverization. Clay as auxiliary
63 parts were added, and the whole was mixed well and pulverized to obtain a 30% wettable powder.
実施例５ 粒剤 化合物番号３の化合物３部にクレー67部、ベントナイ
ト26部を加え、崩壊助剤としてアルキルベンゼンスルホ
ネート0.5部、リグニンスルホン酸ナトリウム3.5部を加
え、全体をよく混合する。これに水を加えて混合後造粒
乾燥し、整粒して３％粒剤を得た。Example 5 Granules 67 parts of clay and 26 parts of bentonite are added to 3 parts of the compound of Compound No. 3, 0.5 parts of alkylbenzenesulfonate and 3.5 parts of sodium ligninsulfonate are added as disintegration aids, and the whole is mixed well. Water was added thereto, mixed, granulated and dried, and sized to obtain 3% granules.
実施例６ 発芽期土壌処理試験 表面積100cm2のポットに水田土壌を詰め、ヒエ種子50
粒と水稲種子10粒を播種し、0.5cmの厚さに覆土をし
た。ヒエ及び水稲種子が土壌表面に発芽した時に湛水深
4.0cmとして本発明化合物の所定量を処理した。薬剤処
理後14日目に調査を行ない次式により表−２の結果を得
た。Example 6 Germination stage soil treatment test A pot with a surface area of 100 cm 2 was filled with paddy field soil, and
Grains and 10 rice seeds were sown and covered with soil to a thickness of 0.5 cm. Waterlogging depth when barley and rice seeds germinated on soil surface
A predetermined amount of the compound of the present invention was treated as 4.0 cm. A survey was conducted 14 days after the drug treatment, and the results in Table 2 were obtained by the following formula.
実施例７ ヒエ2.0葉期処理試験 表面積100cm2のポットに実施例９と同様にヒエ種子と
水稲種子とを播種し、各々が2.0葉期になるまで生育さ
せた。ヒエ及び水稲が各々2.0葉期になった時に湛水深
4.0cmとして本発明化合物の所定量を処理した。薬剤処
理後14日目に調査を行ない前記の式により表−３の結果
を得た。 Example 7 Millet 2.0 Leaf Stage Treatment Test In a pot having a surface area of 100 cm 2 , a barley seed and a rice seed were sown in the same manner as in Example 9, and each was grown until the 2.0 leaf stage. Inundation depth when the millet and paddy rice each reached the 2.0 leaf stage
A predetermined amount of the compound of the present invention was treated as 4.0 cm. Investigation was performed 14 days after the drug treatment, and the results in Table 3 were obtained by the above formula.
〔発明の効果〕 本発明により極めて高度な稲−ヒエ属間選択性と強力
なヒエ殺草活性を有し、かつ使用適期幅の広いすぐれた
除草剤を得ることができる。 [Effects of the Invention] According to the present invention, it is possible to obtain an excellent herbicide having an extremely high rice-millet genus selectivity and a strong herbicidal activity and having a wide suitable use period.
Claims (3)
ルキル基またはハロアルキル基を示し、ｎは０、１、
２、ｍは０、１を示し、Ｒは低級アルキル基、低級アル
コキシアルキル基、ハロアルキル基、低級アルケニル基
または低級アルキニル基を示し、R1は−CONH2、−CSN
H2、−CNまたは−CONH−R2を示し、R2はアルコキシカル
ボニル基またはアルキルカルボニル基を示す。） で表わされる置換テニルスルホンアミド誘導体。1. A compound of the formula [I] (Wherein X and Y independently represent a halogen atom, a lower alkyl group or a haloalkyl group, and n is 0, 1,
2, m indicates 0, 1, R represents a lower alkyl group, a lower alkoxyalkyl group, a haloalkyl group, a lower alkenyl group or a lower alkynyl group, R 1 is -CONH 2, -CSN
H 2 represents —CN or —CONH—R 2 , and R 2 represents an alkoxycarbonyl group or an alkylcarbonyl group. ) A substituted thenylsulfonamide derivative represented by the formula:
ルキル基またはハロアルキル基を示し、ｎは０、１、
２、ｍは０、１を示し、Ｚはハロゲン原子を示す。） で表わされる置換テニルスルホニルハライドと 一般式〔III〕 （式中Ｒは低級アルキル基、低級アルコキシアルキル
基、ハロアルキル基、低級アルケニル基または低級アル
キニル基を示し、R1は−CONH2、−CSNH2、−CNまたは−
CONH−R2を示し、R2はアルコキシカルボニル基またはア
ルキルカルボニル基を示す。） で表わされる化合物を反応させることを特徴とする 一般式〔Ｉ〕 （式中Ｘ及びＹは互いに独立してハロゲン原子、低級ア
ルキル基またはハロアルキル基を示し、ｎは０、１、
２、ｍは０、１を示し、Ｒは低級アルキル基、低級アル
コキシアルキル基、ハロアルキル基、低級アルケニル基
または低級アルキニル基を示し、R1は−CONH2、−CSN
H2、−CNまたは−CONH−R2を示し、R2はアルコキシカル
ボニル基またはアルキルカルボニル基を示す。） で表わされる置換テニルスルホンアミド誘導体の製造方
法。2. The general formula [II] (Wherein X and Y independently represent a halogen atom, a lower alkyl group or a haloalkyl group, and n is 0, 1,
2, m represents 0 and 1, and Z represents a halogen atom. ) And a substituted thenylsulfonyl halide represented by the general formula [III] (Wherein R represents a lower alkyl group, a lower alkoxyalkyl group, a haloalkyl group, a lower alkenyl group or a lower alkynyl group, and R 1 represents —CONH 2 , —CSNH 2 , —CN, or —
It indicates CONH-R 2, R 2 represents an alkoxycarbonyl group or an alkylcarbonyl group. Wherein the compound represented by the general formula [I] is reacted: (Wherein X and Y independently represent a halogen atom, a lower alkyl group or a haloalkyl group, and n is 0, 1,
2, m indicates 0, 1, R represents a lower alkyl group, a lower alkoxyalkyl group, a haloalkyl group, a lower alkenyl group or a lower alkynyl group, R 1 is -CONH 2, -CSN
H 2 represents —CN or —CONH—R 2 , and R 2 represents an alkoxycarbonyl group or an alkylcarbonyl group. A method for producing a substituted thenylsulfonamide derivative represented by the formula:
ルキル基またはハロアルキル基を示し、ｎは０、１、
２、ｍは０、１を示し、Ｒは低級アルキル基、低級アル
コキシアルキル基、ハロアルキル基、低級アルケニル基
または低級アルキニル基を示し、R1は−CONH2、−CSN
H2、−CNまたは−CONH−R2を示し、R2はアルコキシカル
ボニル基またはアルキルカルボニル基を示す。） で表わされる置換テニルスルホンアミド誘導体を有効成
分として含有することを特徴とする選択性除草剤。3. A compound of the general formula [I] (Wherein X and Y independently represent a halogen atom, a lower alkyl group or a haloalkyl group, and n is 0, 1,
2, m indicates 0, 1, R represents a lower alkyl group, a lower alkoxyalkyl group, a haloalkyl group, a lower alkenyl group or a lower alkynyl group, R 1 is -CONH 2, -CSN
H 2 represents —CN or —CONH—R 2 , and R 2 represents an alkoxycarbonyl group or an alkylcarbonyl group. ) A selective herbicide characterized by containing a substituted thenylsulfonamide derivative represented by the following formula as an active ingredient:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1987788A JP2639428B2 (en) | 1988-01-30 | 1988-01-30 | Substituted thenylsulfonamide derivatives, their preparation and selective herbicides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1987788A JP2639428B2 (en) | 1988-01-30 | 1988-01-30 | Substituted thenylsulfonamide derivatives, their preparation and selective herbicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01197477A JPH01197477A (en) | 1989-08-09 |
| JP2639428B2 true JP2639428B2 (en) | 1997-08-13 |
Family
ID=12011438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1987788A Expired - Lifetime JP2639428B2 (en) | 1988-01-30 | 1988-01-30 | Substituted thenylsulfonamide derivatives, their preparation and selective herbicides |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2639428B2 (en) |
-
1988
- 1988-01-30 JP JP1987788A patent/JP2639428B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01197477A (en) | 1989-08-09 |
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