JPS60120849A - Trifluoromethanesulfon anilide derivative, its preparation, and herbicide containing it as active ingredient - Google Patents
Trifluoromethanesulfon anilide derivative, its preparation, and herbicide containing it as active ingredientInfo
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- JPS60120849A JPS60120849A JP22889083A JP22889083A JPS60120849A JP S60120849 A JPS60120849 A JP S60120849A JP 22889083 A JP22889083 A JP 22889083A JP 22889083 A JP22889083 A JP 22889083A JP S60120849 A JPS60120849 A JP S60120849A
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Abstract
Description
【発明の詳細な説明】
本発明は、一般式
〔式中、Rは水素原子、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表わし、R2は水素原子
、低級アルキル基または低級アルキニル基を表わし、X
はハロゲン原子を表わす。但し、R1とR21よ同時に
水素原子を表わすことはない。〕
で示されるトリフルオロメタンスルポンアニリド誘導体
(以゛ド、本発明化、合物と記す。)、その製造法およ
びそれを有効成分とする除草剤に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula [wherein R represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, or a lower alkynyl group, and R2 represents a hydrogen atom, a lower alkyl group, or a lower alkynyl group] ,X
represents a halogen atom. However, R1 and R21 do not represent hydrogen atoms at the same time. ] The present invention relates to a trifluoromethanesulponanilide derivative (hereinafter referred to as the invention or compound) shown in the following, a method for producing the same, and a herbicide containing the same as an active ingredient.
ある種のトリフルオロメタンスルホンアニリドm導体、
例えば、2.4−ジクロロトリ7 thオロメタンスル
ホンアニリド、2−メチル−4−フェニルスルホニルト
リフルオロメタンスルホンアニリドおよび8−(N、N
−ジメチルスルファモイル)トリフルオロメタンスルホ
ンアニリドが除草剤の有効成分として用いうろことは、
米国特許第8689474号明細書、特公昭54−11
297号公報および米国特許第8920444号明細書
に記載されている。しかしながら、これらの化合物は、
除草剤の有効成分として必ずしも常に充分なものである
とはいえなL)。Certain trifluoromethanesulfonanilide m-conductors,
For example, 2,4-dichlorotri7th olomethanesulfonanilide, 2-methyl-4-phenylsulfonyltrifluoromethanesulfonanilide and 8-(N,N
-Dimethylsulfamoyl) trifluoromethanesulfonanilide is used as an active ingredient in herbicides.
U.S. Patent No. 8,689,474, Japanese Patent Publication No. 1983-11
No. 297 and US Pat. No. 8,920,444. However, these compounds
L) is not always sufficient as an active ingredient in herbicides.
本発明化合物は畑地の茎葉処理および土壌処理において
、問題となる種々の雑草、例えば、ソバカズラ、サナエ
タデ、スベリヒエ、ハコベ、シロザ、アオビユ(アオゲ
イトウ)、ダイコン、ノハラガラシ、ナズナ、アメリカ
ッノクサネム、エビスグサ、イチビ、アメリカキンゴジ
カ、アメリカアサガオ、マルバアサガオ、ヨウシュチョ
ウセンアサガオ、イヌホオズキ、オオイヌノフグリ、オ
ナモミ、ヒマワリ、イヌカミツレ等の広葉雑草、ヒエ、
イヌビエ、エノコログサ、メヒシバ、スズメノカタビラ
、エンバク、カラスムギ、セイバンモロコシ等のイ*[
i草およびコゴメガヤッリ、ハマスゲ等のカヤツリグサ
科雑草等に対して除草効力を有し、しかもいくつかの本
発明化合物はイネ、ダイズ、ワタ等の主要作物に対して
問題となるような薬害を示さない。The compound of the present invention can be used to treat various weeds that are problematic in the treatment of foliage and soil in upland areas, such as freckle weeds, Japanese knotweed, purslane, chickweed, whiteweed, Japanese radish, Japanese radish, Japanese radish, shepherd's purse, American cornflower, Ebisu grass, Broad-leafed weeds such as Japanese grasshopper, American golden deer, American morning glory, Malva morning glory, Japanese morning glory, Japanese Physalis, Japanese dogfish, Japanese fir tree, sunflower, Japanese dogwood, etc., barnyard grass,
I *[
The compounds of the present invention have herbicidal effects against weeds of the Cyperaceae family, such as I-grass and Cyperaceae, such as Cyperaceae, and, moreover, some of the compounds of the present invention do not cause problematic phytotoxicity to major crops such as rice, soybeans, and cotton. .
また、本発明化合物は水田の湛水処理においてMiMと
なル種々の雑草、例えば、タイヌビエ等のイネ科雑草、
アゼナ、キカシグサ、ミゾハコへ等の広葉雑草、タマガ
ヤツリ、ホタルイ。In addition, the compound of the present invention can be used to treat various weeds such as MiM in the flooding treatment of paddy fields, such as grass weeds such as Japanese grasshopper, etc.
Broad-leafed weeds such as azalea, sagebrush, and cypress, as well as cypress and firefly.
マツバイ、ミズガヤツリ等のカヤツリグサ科雑草、コナ
ギ、ウリカワ等に対して除草効力を有し、しかもイネに
対して問題となるような薬害を示さない、
本発明化合物は、一般式
〔式中、Xは前記と同じ意味を表わす。〕で示されるベ
ンゼンスルホニルクロリド誘導体と一般式
〔式中、R1およびR2は前記と同じ意味を表わすう
〕
で示されるアミン誘導体とを溶媒中、脱ハロゲン化水素
剤の存在下、0°C〜100℃、0.5時間〜10時間
反応させることによって製造することができる。The compound of the present invention has a herbicidal effect against weeds of the Cyperaceae family, such as Cyperus japonica and Cyperus japonica, and does not cause any harmful effects on rice. It has the same meaning as above. ] and the benzenesulfonyl chloride derivative represented by the general formula [wherein R1 and R2 have the same meanings as above]
] It can be produced by reacting the amine derivative represented by the following in a solvent in the presence of a dehydrohalogenating agent at 0° C. to 100° C. for 0.5 hours to 10 hours.
反応に供される試剤の量は、ベンゼンスルホニルクロリ
ド誘導体Cm) 1当量に対して、アミン誘導体〔劃は
0.9〜8当量、脱ハロゲン化水素剤は0.9〜2当量
である。The amounts of the reagents used in the reaction are 0.9 to 8 equivalents for the amine derivative and 0.9 to 2 equivalents for the dehydrohalogenating agent per 1 equivalent of the benzenesulfonyl chloride derivative Cm).
溶媒としては、ベンゼン、トルエン、キシレン等の芳香
族炭化水素類、クロロホルム、四塩化炭素、ジクロロエ
タン、クロロベンゼン、ジクロロベンゼン等のハロゲン
化炭化水素If 、ジエチルエーテル、ジイソプロピル
エーテル、ジオキサン、テトラヒドロフラノ、ジエチレ
ングリコールジメチルエーテル等のエーテル類、アセト
ン、メチルエチルケトン、メチルイソブチルケトン、イ
ソホロン、シクロヘキサノン等のケトン類、メタノール
、エタノール、イソプロパツール、t−ブタノール、オ
クタツール、シクロヘキサノール、メチルセロソルブ、
ジエチレングリコール、グリセリン等のアルコール類、
蟻酸エチル、酢酸エチル、酢酸ブチル、炭酸ジエチル等
のエステル類、ニトロユタン、ニトロベンゼン等のニト
ロ化物、アセトニトリル、イソブチロニトリル等のニト
リル類、ピリジン、トリエチルアミン、N、N−ジエチ
ルアニリン、トリブチルアεン、N−メチルモルホリン
等の第三級アミン類、ホルムアミド、N、N−ジメチル
ホルムアミド、アセトアミド等の酸アミド類、ジメチル
スルホキシド、スルホラン等の硫黄化合物、水等あるい
は、それらの混合物があげられる。Examples of solvents include aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, and dichlorobenzene, diethyl ether, diisopropyl ether, dioxane, tetrahydrofurano, and diethylene glycol dimethyl ether. Ethers such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, ketones such as cyclohexanone, methanol, ethanol, isopropanol, t-butanol, octatool, cyclohexanol, methyl cellosolve,
Alcohols such as diethylene glycol and glycerin,
Esters such as ethyl formate, ethyl acetate, butyl acetate, diethyl carbonate, nitrites such as nitrobutane and nitrobenzene, nitriles such as acetonitrile and isobutyronitrile, pyridine, triethylamine, N,N-diethylaniline, tributylamine, Examples include tertiary amines such as N-methylmorpholine, acid amides such as formamide, N,N-dimethylformamide, and acetamide, sulfur compounds such as dimethyl sulfoxide and sulfolane, water, and mixtures thereof.
脱ハロケン化水素剤としては、ピリジン、トリエチルア
ミン、N、N−ジエチルアニリン等の有機塩基、水酸化
ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カ
リウム、水素化ナトリウム等の無機塩基、ナトリウムメ
トキシド、ナトリウムエトキシド等のアルカリ金属アル
コキシド等があげられる。Examples of dehydrogenation agents include organic bases such as pyridine, triethylamine, N,N-diethylaniline, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, and sodium hydride, sodium methoxide, and sodium hydroxide. Examples include alkali metal alkoxides such as ethoxides.
反応終了後の反応液は、濃縮後酸性にし、生じた沈殿を
有機溶媒抽出および濃縮等の通常の後処理を行い、必要
ならば、クロマトグラフィー、再結晶等の操作によって
精製する。After the reaction is completed, the reaction solution is concentrated and acidified, and the resulting precipitate is subjected to conventional post-treatments such as organic solvent extraction and concentration, and if necessary, purified by operations such as chromatography and recrystallization.
次に本発明化合物の製造例を示す。Next, production examples of the compounds of the present invention will be shown.
製造例1 (本発明化合物1の製造)
2.4−ジクロロ−5−)リフルオロメタンスルホンア
ミドベンゼンスルホニルクロリド4gのテトラヒドロフ
ラン50 mL 溶液に40%メチルアミン水溶液1.
71を加え、40℃で2時間反応した。Production Example 1 (Production of Compound 1 of the Present Invention) A 40% aqueous methylamine solution 1.
71 was added and reacted at 40°C for 2 hours.
反応後濃縮し、5%塩酸水を加えると油状物が沈殿した
、これをクロロホルムで抽出シ、有機層を水洗い後溶媒
を留去した。これをトルエンで再結晶して8.2gの2
.4−ジクロロ−5−(N−メチルスルファモイル)ト
リフルオロメタンスルホンアニリドヲ得り。After the reaction, the mixture was concentrated, and 5% aqueous hydrochloric acid was added to precipitate an oil. This was extracted with chloroform, the organic layer was washed with water, and the solvent was distilled off. This was recrystallized with toluene and 8.2g of 2
.. 4-dichloro-5-(N-methylsulfamoyl)trifluoromethanesulfone anilide was obtained.
融点166〜168.5℃
このような製造法によって製造できろ本発明化合物のい
くつかを、第1表に示す。Melting point: 166-168.5°C Some of the compounds of the present invention that can be produced by such a production method are shown in Table 1.
第 1 表
本発明化合物を製造する場合、原料化合物であるベンゼ
ンスルホニルクロリド誘導体CII)は、次のような方
法にて製造することができる。Table 1 When producing the compounds of the present invention, the benzenesulfonyl chloride derivative CII), which is a raw material compound, can be produced by the following method.
(1) まず一般式
6式中、Xはハロゲン原子を表わす、〕で示される2、
4−ジハロトリフルオロメタンスルホンアニリドと、こ
れに対して1〜15当量の発煙硫酸とを硫酸中、5°C
〜80℃、1時間〜2時間反応させた後、反応液を氷水
中に、20℃以fに保ちながら注ぎ、次いで得られた水
溶液を水酸化ナトリウム、水酸化カリウム等のアルカリ
水溶液で中和し、濃縮乾固して、粉状の一般式
C式中、Xは前記と同し意味を表わす。〕で示されるベ
ンゼンスルホン酸誘導体ノアルカリ塩を得る。(1) First, 2 represented by the general formula 6, where X represents a halogen atom,
4-dihalotrifluoromethanesulfonanilide and 1 to 15 equivalents of fuming sulfuric acid in sulfuric acid at 5°C.
After reacting at ~80°C for 1 to 2 hours, the reaction solution is poured into ice water while maintaining the temperature below 20°C, and the resulting aqueous solution is then neutralized with an alkaline aqueous solution such as sodium hydroxide or potassium hydroxide. The product was concentrated to dryness to give a powder of the general formula C, where X has the same meaning as above. ] A benzenesulfonic acid derivative alkali salt is obtained.
(2> 次いで、得られたベンゼンスルホン酸誘導体〔
■〕のrルカリ塩と、これに対して1〜2当量の五塩化
リンとを20 ”C−180’C20,1時間〜2時間
反応させた後、反応液を氷水中に注ぎ、得られた沈殿物
を炉別または有機溶媒抽出および濃縮等の通常の後処理
を行い、必要ならば、クロマトグラフィー、再結晶等の
操作によって精製することにより、目的のベンゼンスル
ホニルクロリド誘導体〔ff)を得ることができる。(2> Then, the obtained benzenesulfonic acid derivative [
(2)] and 1 to 2 equivalents of phosphorus pentachloride to 20"C-180'C20, after reacting for 1 to 2 hours, the reaction solution was poured into ice water and the obtained The desired benzenesulfonyl chloride derivative [ff] is obtained by subjecting the precipitate to usual post-treatments such as furnace separation or organic solvent extraction and concentration, and if necessary, purifying it by operations such as chromatography and recrystallization. be able to.
次にこのベンゼンスルホニルクロリド誘導体の製造例を
参考例として示す。Next, a production example of this benzenesulfonyl chloride derivative will be shown as a reference example.
参考例
2.4−ジクロロトリフルオロメタンスルホンアニリド
29.4gを濃硫Ml 4 B ml に溶かし、60
%発煙硫酸48 mA を10〜2゜°Cで、滴下した
。滴下終了後氷水中に反応液を注ぎ、力性ソーダ水溶液
で中和した。中和後濃縮乾固し、エタノールを加え加熱
還流した。熱濾過をし、エタノール抽出液を濃縮乾固し
て401の粉末を得た。この粉末に五塩化リン20.8
gを加えると反応し、還流が始まる。還流がおさまって
から180 ’C位のオイル浴で2時間加熱した。反応
後氷水の中に加え、結晶を炉別水洗して乾燥し、80.
5fの2.4−ジクロロ−5−トリフルオロメタンスル
ホンアミドベンゼンスルホニルクロリドを得た。融点1
08〜105℃
本発明化合物を除草剤の有効成分として用いる場合は、
通常固体担体、液体担体、界面活性剤その他の製剤用補
助剤と混合して、乳剤、水和剤、懸濁剤、粒剤等に製剤
する。Reference Example 2. 29.4 g of 4-dichlorotrifluoromethanesulfonanilide was dissolved in concentrated sulfur Ml 4 B ml, and 60
% oleum at 48 mA was added dropwise at 10-2°C. After the addition was completed, the reaction solution was poured into ice water and neutralized with aqueous sodium hydroxide solution. After neutralization, the mixture was concentrated to dryness, ethanol was added, and the mixture was heated to reflux. After hot filtration, the ethanol extract was concentrated to dryness to obtain 401 powder. This powder contains 20.8 phosphorus pentachloride.
When g is added, a reaction occurs and reflux begins. After the reflux subsided, the mixture was heated in an oil bath at about 180'C for 2 hours. After the reaction, the crystals were added to ice water, washed in a separate furnace with water, and dried.80.
5f of 2,4-dichloro-5-trifluoromethanesulfonamidobenzenesulfonyl chloride was obtained. Melting point 1
08-105°C When using the compound of the present invention as an active ingredient of a herbicide,
It is usually mixed with solid carriers, liquid carriers, surfactants, and other formulation auxiliaries to formulate emulsions, wettable powders, suspensions, granules, etc.
これらの製剤には有効成分として本発明化合物を、重量
比で0.1〜90%、好ましくは1〜80%含有する。These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.1 to 90%, preferably 1 to 80%.
固体担体には、カオリンクレー、アッタバルジャイトク
レー、ベントナイト、酸性白土、パイロフィライト、タ
ルク、珪藻土、方解石、クルミ粉、尿素、硫酸アンモニ
ウム、合成含水酸化珪素等の微粉末あるいは粒状物があ
り、液体担体には、キシレン、メチルナフタレン等の芳
香族炭化71類、イソプロパツール、エチレングリコー
ル、セロソルブ等のアルコール類、アセトン、シクロヘ
キサノン、イソホロン等のケトン類、大豆油、綿実油等
の植物油、ジメチルスルホキシド、アセトニトリル、水
等がある。Solid carriers include fine powders or granules such as kaolin clay, attabulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, walnut powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide; The carriers include aromatic carbon 71 such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and isophorone, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, Examples include acetonitrile and water.
乳化、分散、湿展等のために用いられる界面活性剤には
、アルキル硫酸エステル塩、アルキル(アリール)スル
ホン酸塩、ジアルキルスルホコハク酸塩、ポリオキシエ
チレンアルキルアリールエーテルリン酸エステル塩等の
陰イオン界面活性剤、ポリオキシエチレンアルキルエー
テル、ポリオキシエチレンアルキルアリールエーテル、
ポリオキシエチレンポリオキシプロピレンブロックコポ
リマー、ソルビタン脂肪酸エステル、ポリオキシエチレ
ンソルビタン脂肪酸エステル等の非イオン界面活性剤等
がある。Surfactants used for emulsification, dispersion, wetting, etc. include anionic surfactants such as alkyl sulfate salts, alkyl (aryl) sulfonate salts, dialkyl sulfosuccinate salts, and polyoxyethylene alkylaryl ether phosphate salts. Surfactant, polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether,
Examples include nonionic surfactants such as polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters.
製剤用補助剤には、リグニンスルホン酸塩、アルギン酸
塩、ポリビニルアルコール、アラビアがム、CMC(カ
ルボキシメチルセルロース)、PAP(酸性リン酸イソ
プロピル)等力する。Auxiliary agents for formulation include lignin sulfonate, alginate, polyvinyl alcohol, arabic gum, CMC (carboxymethyl cellulose), PAP (isopropyl acid phosphate), and the like.
次に製剤例を示す。なお、本発明化合物は第1表の化合
物番号で示す。部は重量部を示す。Examples of formulations are shown below. The compounds of the present invention are indicated by compound numbers in Table 1. Parts indicate parts by weight.
製剤例1
本発明化合物9.50部、リグニンスルホン酸カルシウ
ム8部、ラウリル硫酸ナトリウム2部および合成含水酸
化珪素45部をよく粉砕混合して水和剤を得る。Formulation Example 1 9.50 parts of the compound of the present invention, 8 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain a wettable powder.
製剤例2
本発明化合物4.10部、ポリオキシエチレンスチリル
フェニルエーテル14部、ドデシルベンゼンスルホノ酸
カルシウム6部およびシクロヘキサノン70部をよく混
合して乳剤を得る。Formulation Example 2 4.10 parts of the compound of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 70 parts of cyclohexanone are thoroughly mixed to obtain an emulsion.
製剤例8
本発明化合物7.2部、合成含水酸化珪素1部、リグニ
ンスルホン酸カルシウム2部、ベントナイト80部およ
びカオリンクレー65部をよく粉砕混合し、水を加えて
よく練り合せた後、造粒乾燥して粒剤を得る。Formulation Example 8 7.2 parts of the compound of the present invention, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 80 parts of bentonite, and 65 parts of kaolin clay were thoroughly ground and mixed, water was added, and the mixture was thoroughly kneaded. The granules are dried to obtain granules.
製剤例4
本発明化合物5.25部、ポリオキシエチレンソルビタ
ンモノオレエート9部、CMC8部、水69部を混合し
、粒度が5ミクロン以下になるまで湿式粉砕して懸濁剤
を得る。Formulation Example 4 5.25 parts of the compound of the present invention, 9 parts of polyoxyethylene sorbitan monooleate, 8 parts of CMC, and 69 parts of water are mixed and wet-pulverized until the particle size becomes 5 microns or less to obtain a suspension.
このようにして製剤された本発明化合物は、雑草の出芽
前または出芽後に土壌処理、茎葉処理または湛水処理す
る。The compound of the present invention thus formulated is treated with soil, foliage, or flooding before or after the emergence of weeds.
土壌処理には、土壌表面処理、土壌混和処理等があり、
茎葉処理には、植物体の上方からの処理のほか、作物に
付着しないよう雑草に限って処理する局部処理等がある
、
また、他の除草剤と混合して用いることにより、除草効
力の増強を期待できる。さらに、殺虫剤、殺ダニ剤、殺
線虫剤、殺菌剤、植物生長調節剤、肥料、土壌改良剤等
と混合して用いることもできる。Soil treatment includes soil surface treatment, soil mixing treatment, etc.
In addition to treatments from above the plant body, foliar treatments include local treatments that treat only weeds so that they do not attach to crops.Additionally, they can be used in combination with other herbicides to increase herbicidal efficacy. You can expect. Furthermore, it can be used in combination with insecticides, acaricides, nematicides, fungicides, plant growth regulators, fertilizers, soil conditioners, and the like.
なお、本発明化合物は、水田、畑地、果樹園、牧草地、
芝生地、森林あるいは非農耕地等の除草剤の有効成分と
して用いることができる。The compound of the present invention can be used in rice fields, fields, orchards, pastures,
It can be used as an active ingredient in herbicides for lawns, forests, non-agricultural lands, etc.
本発明化合物を除草剤の有効成分として用いる場合、そ
の施用量は、気象条件、製剤形態、施用時期、方法、場
所、対象雑草、対象作物等によっても異なるが、通常1
アールあたり11〜200g、好ましくは、4g〜10
0fであり、乳剤、水和剤、懸濁剤等は、通常その所定
量を1アールあたり1す、ソトル〜101)・ソトルの
(必要ならば、展着剤等の補助剤を添加した)水で希釈
して処理し、粒剤等は通常なんら希釈することなくその
ま\処理する。When the compound of the present invention is used as an active ingredient of a herbicide, the application amount varies depending on weather conditions, formulation form, application timing, method, location, target weeds, target crops, etc., but usually 1.
11-200g per are, preferably 4g-10
Emulsions, wetting agents, suspending agents, etc. are usually used in a prescribed amount per are, sotol to 101) (if necessary, auxiliary agents such as spreading agents are added). It is treated by diluting it with water, and granules and the like are usually treated as they are without any dilution.
展着剤には、前記の界面活性剤のほか、ポリオキシエチ
レン樹111酸(エステル)、リグニンスルホン酸塩、
アビエチン酸塩、ジナフチルメタンジスルホン酸塩、パ
ラフィン等がある。In addition to the above-mentioned surfactants, the spreading agent includes polyoxyethylene resin 111 acid (ester), lignin sulfonate,
Examples include abietate, dinaphthylmethane disulfonate, and paraffin.
次に、本発明化合物が除草剤の有効成分として有用であ
ることを試験例で示す。なお、本発明化合物は、第1表
の化合物番号で示し、比較対照に用いた化合物は第2表
の化合物記号で示す。Next, test examples demonstrate that the compounds of the present invention are useful as active ingredients of herbicides. The compounds of the present invention are indicated by the compound numbers in Table 1, and the compounds used for comparison are indicated by the compound symbols in Table 2.
第2表
また、除草効力は、調査時の供試植物の出芽および生育
阻害の程度を肉眼観察し、化合物を供試していない場合
と全くないしほとんど違いがないものを「0」とし、供
試植物が枯死ないし生育が完全に阻害されているものを
「5」として、0〜5の6段階に評価し、0.1.2.
8.4.5で示す。Table 2 In addition, herbicidal efficacy is determined by visually observing the degree of budding and growth inhibition of the test plants during the survey, and ``0'' indicates that there is no or almost no difference from the case where no compound is used. The plant is rated on a scale of 0 to 5, with "5" indicating that the plant has died or its growth has been completely inhibited.
8.4.5.
試験例1 畑地土壌処理試験
直径10m、深さ10cmの円筒型プラスチックポ・ソ
トに畑地土壌を詰め、ヒエ、エンバク、マルバアサガオ
、イチビを播種し、覆土した。製剤例2に準じて供試化
合物を乳剤にし、その所定量を、1アールあたり10リ
ツトル相当の水で希釈し、小型噴霧器で土壌表面に処理
した。処理後20日間温室内で育成し、除草効力を調査
した。その結果を第8表に示す。Test Example 1 Upland Soil Treatment Test A cylindrical plastic container with a diameter of 10 m and a depth of 10 cm was filled with upland soil, and barnyard grass, oats, morning glory, and Japanese radish were sown and covered with soil. The test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the emulsion was diluted with water equivalent to 10 liters per are, and the emulsion was applied to the soil surface using a small sprayer. After treatment, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 8.
第8表
試験例2 畑地茎葉処理試験
直径10画、深さ10画の円筒型プラスチックポットに
畑地土壌を詰め、ヒエ、エンバク、ダイコン、イチビを
播種し、温室内で10日間育成した。その後、製剤例2
に準じて供試化合物を乳剤にし、その所定量を、1アー
ルあたり10リツトル相当の展着剤を含む水で希釈し、
小型噴霧器で植物体の上方から茎葉処理した。処理後2
0日間温室内で育成し、除草効力を調査した。その結果
を第4表に示す。Table 8 Test Example 2 Field field stem and leaf treatment test A cylindrical plastic pot with a diameter of 10 squares and a depth of 10 squares was filled with field soil, and barnyard grass, oats, radish, and Japanese radish were sown and grown in a greenhouse for 10 days. Then, Formulation Example 2
Make the test compound into an emulsion according to
The foliage was treated from above the plant using a small sprayer. After processing 2
The plants were grown in a greenhouse for 0 days and their herbicidal efficacy was investigated. The results are shown in Table 4.
試験例4 畑地土壌処理試験
面積88x2Bcd、深さ11傷のバットに畑地土壌を
詰め、ダイズ、ワタ、テンサイ、マルバアサガオ、オナ
モミ、イチビ、エビスグサ、イヌビエを播種し、ハマス
ゲの塊茎を移植し、1〜2cmの厚さに覆土した。製剤
例2に準じて供試化合物を乳剤にし、その所定量を、1
アールあたりlOリットル相当の水で希釈し、小型噴霧
器で土壌表面に処理した。Test Example 4 Upland Soil Treatment Test A vat with an area of 88 x 2 Bcd and a depth of 11 wounds was filled with upland soil, and soybean, cotton, sugar beet, Japanese morning glory, Japanese fir, Japanese yam, Ebisugusa, and Japanese commonweed were sown, and tubers of Japanese commonweed were transplanted. The soil was covered with soil to a thickness of ~2 cm. The test compound was made into an emulsion according to Formulation Example 2, and a predetermined amount of the emulsion was added to 1
It was diluted with 10 liters of water per area and applied to the soil surface using a small sprayer.
処理後20日間温室内で育成し、除草効力を調査した。After treatment, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated.
その結果を第6表に示す。The results are shown in Table 6.
第6表Table 6
Claims (1)
ニル基または低級アルキニル基を表わし、R2は水素原
子、低級アルキル基または低級アルキニル基を表わし、
xはハロゲン原子を表わす。但し、R1とR2は同時に
水素原子を表わさない。〕 で示されるトリフルオロメタンスルホンアニリド誘導体
。 (2) 一般式 〔式中、Xはハロゲン原子を表わす。〕で示されるベン
ゼンスルホニルクロリド誘導体と一般式 〔式中、R1は水素原子、低級アルキル基、低級アルケ
ニル基または低級アルキ=I14を表わし、R2は水素
原子、低級アルキル基または低級アルキニル基を表わす
。但し、R1とR2は同時に水素原子を表わさない。〕
で示されるアミン誘導体とを反応させることを特徴とす
る一般式 〔式中、R1,R2およびXは前記と同じ廊味を表わす
。〕 で示すしるトリフルオロメタンスルポンアニリド誘導体
の製造法。 (8) 一般式 〔式中、R1は水素原子、低級アルキル基、低級アルケ
ニル基Iたは低級アルキニル基を表わし、R2は水素早
子、低級アルキル基または低級アルキニル基を表わし、
Xはハロゲン原子を表わす。但し、R1とR2は同時に
水素原子を表わすことはない。〕 で示されるトリフルオロメタンスルホン酸アニリド誘導
体を有好成分とすることを特徴とする除草剤。[Scope of Claims] (1) In the general formula C, R1 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, or a lower alkynyl group, and R2 represents a hydrogen atom, a lower alkyl group, or a lower alkynyl group,
x represents a halogen atom. However, R1 and R2 do not represent hydrogen atoms at the same time. ] A trifluoromethanesulfonanilide derivative represented by (2) General formula [wherein, X represents a halogen atom]. A benzenesulfonyl chloride derivative represented by the general formula [wherein R1 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, or lower alkyl=I14], and R2 represents a hydrogen atom, a lower alkyl group, or a lower alkynyl group. However, R1 and R2 do not represent hydrogen atoms at the same time. ]
A general formula characterized by reacting with an amine derivative represented by the formula [wherein R1, R2 and X represent the same groups as above]. ] A method for producing a trifluoromethanesulponanilide derivative shown in the following. (8) General formula [wherein R1 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group I, or a lower alkynyl group, and R2 represents a hydrogen atom, a lower alkyl group, or a lower alkynyl group,
X represents a halogen atom. However, R1 and R2 do not represent hydrogen atoms at the same time. ] A herbicide characterized by containing a trifluoromethanesulfonic acid anilide derivative represented by the following as a preferred ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP22889083A JPS60120849A (en) | 1983-12-02 | 1983-12-02 | Trifluoromethanesulfon anilide derivative, its preparation, and herbicide containing it as active ingredient |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP22889083A JPS60120849A (en) | 1983-12-02 | 1983-12-02 | Trifluoromethanesulfon anilide derivative, its preparation, and herbicide containing it as active ingredient |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS60120849A true JPS60120849A (en) | 1985-06-28 |
Family
ID=16883456
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP22889083A Pending JPS60120849A (en) | 1983-12-02 | 1983-12-02 | Trifluoromethanesulfon anilide derivative, its preparation, and herbicide containing it as active ingredient |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS60120849A (en) |
-
1983
- 1983-12-02 JP JP22889083A patent/JPS60120849A/en active Pending
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