JPS6222981B2 - - Google Patents

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Publication number
JPS6222981B2
JPS6222981B2 JP13664880A JP13664880A JPS6222981B2 JP S6222981 B2 JPS6222981 B2 JP S6222981B2 JP 13664880 A JP13664880 A JP 13664880A JP 13664880 A JP13664880 A JP 13664880A JP S6222981 B2 JPS6222981 B2 JP S6222981B2
Authority
JP
Japan
Prior art keywords
compound
methoxycarbonyl
acetylsulfanilamide
weeds
germination
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
JP13664880A
Other languages
Japanese (ja)
Other versions
JPS5759855A (en
Inventor
Kanji Ito
Kenji Igawa
Hisajiro Yukinaga
Jitsuo Sugita
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.)
Shionogi and Co Ltd
Original Assignee
Shionogi and 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 Shionogi and Co Ltd filed Critical Shionogi and Co Ltd
Priority to JP13664880A priority Critical patent/JPS5759855A/en
Publication of JPS5759855A publication Critical patent/JPS5759855A/en
Publication of JPS6222981B2 publication Critical patent/JPS6222981B2/ja
Granted legal-status Critical Current

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

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

本発明はN1−メトキシカルボニル−N4−−
−メチル−−クロルプノキシプロピオ
ニルスルフアニルアミド、N1−メトキシカル
ボニル−N4−・−ゞクロルプノキシア
セチルスルフアニルアミド、N1−メトキシカル
ボニル−N4−・−ゞメチルプノキシア
セチルスルフアニルアミド、N1−メトキシカル
ボニル−N4−−ニトロプノキシアセチル
スルフアニルアミド、N1−メトキシカルボニル
−N4−−ニトロプノキシアセチルスルフ
アニルアミド、N1−メトキシカルボニル−N4−
・−ゞニトロプノキシアセチルスルフ
アニルアミドおよびN1−アセチル−N4−−メ
チル−−クロルプノキシアセチルスルフア
〓〓〓〓〓
ニルアミドよりなる矀より遞ばれたN4−プノ
キシアルカノむルスルフアニルアミド類、
および、このN4−プノキシアルカノむルスル
フアニルアミド類たたはその氎溶性金属塩のうち
少くずも個を有効成分ずしお含有する陀草剀に
係る。 䞊蚘匏の化合物は䟋えば、 察応するプノキシアルカノむル誘導䜓
を、察応するスルフアニルアミド類ず反応
させるこずによ぀お補造する、がハロゲンの堎
合、反応は䞍掻性有機溶媒䞭、塩圢成剀あるいは
ハロゲン化氎玠捕捉剀、端的には無機あるいは有
機塩基の存圚䞋に接觊させるこずにより進行す
る。 のプノキシアルカノむルハラむド類ず
しおは、たずえば−ニトロプノキシ酢酞、
−ニトロプノキシ酢酞、・−ゞニトロプ
ノキシ酢酞、・−ゞクロルプノキシ酢酞、
・−ゞメチルプノキシ酢酞、−メチル−
−クロルプノキシ酢酞、−メチル−−ク
ロルプノキシプロピオン酞のクロリドたたはブ
ロミドが挙げられる。 のスルフアニルアミド類ずしおは、たず
えばN1−メトキシカルボニルスルフアニルアミ
ド、N1−アセチルスルフアニルアミドなどが挙
げられる。 たた塩圢成剀ずしおは氎玠化ナトリりム、氎玠
化カリりム、氎酞化ナトリりム、氎酞化カリり
ム、ナトリりムアミド、ナトリりムアルコキシド
などが挙げられ、塩化氎玠捕捉剀ずしおはピリゞ
ン、トリ゚チルアミンなどが挙げられる。 䞍掻性有機溶媒ずしおは、ベンれン、トル゚ン
などの芳銙族炭化氎玠、ゞオキサン、テトラヒド
ロフラン、ゞ゚チル゚ヌテル、ピリゞン、ゞメチ
ルホルムアミド、ゞメチルスルホキシドなどが挙
げられる。溶媒ずしお前蚘塩化氎玠捕捉剀の機胜
を兌ね備えおいるもの、たずえばピリゞンの䜿甚
は補造工皋の簡玠化にず぀お䟿利である。 反応は通垞宀枩あるいは僅かに加枩した状態で
行われるが、堎合によりのスルフアニルア
ミド類ず溶媒ずの混合物を冷华しおおき、これに
の酞ハラむドを添加あるいはその溶液を滎
䞋するなどの方法もずり埗る。その埌所望の条件
で反応を進行させ、最適の収率を埗るよう液性を
調敎しお反応を完了させる。 たた、出発物質および生成物質の物性を蚱す堎
合、たずえば生成物質の融点が䞡出発物質の融点
より充分高く、いずれも熱に察しおの安定性が高
い堎合などは、プノキシ酢酞、プノキシプロ
ピオン酞類をハラむドずするこずなく遊離カルボ
ン酞のたたで、スルフアニルアミド類ず共に枛圧
条件䞋に熔融させおも盎接に目的物質を埗るこず
ができる。 䞊蚘の方法で埗られたの化合物は適圓な
溶媒、たずえば含氎メタノヌルから再結晶する
か、あるいはクロマトグラフむヌ凊理により粟補
される。たた、埗られた化合物を氎䞭に溶解させ
氎酞化アルカリ金属あるいはアルカリ土類金属を
䜜甚させお、これらの金属塩ずするこずもでき
る。 本発明の化合物を陀草剀ずしお䜿甚する
堎合は通垞これらの化合物に察し䞍掻性な液䜓た
たは固䜓の担䜓で皀釈し、必芁があれば適圓な助
剀たずえば界面掻性剀などをこれに加えお乳剀、
粉剀、氎和剀、粒剀などの圢態で䜿甚する。さら
に必芁があれば他の有効成分を混入しお䜿甚する
こずも可胜である。 本発明においお䜿甚する液䜓の担䜓ずしおは
皮々の有機溶剀たずえばケロシン、ベンれン、キ
シレンなどの炭化氎玠類、クロルベンれン、ゞク
ロル゚チレンなどのハロゲン化炭化氎玠類、アル
コヌル類、アセトンなどのケトン類などが挙げら
れ、たた固䜓の担䜓ずしおはベントナむト、カオ
リン、クレヌ、タルク、酞性癜土、けいそう土、
硅砂、埮粉状シリカ、炭酞カルシりムなどが挙げ
られる。 たた界面掻性剀ずしおは、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、高玚
アルコヌル硫酞゚ステル、ポリオキシ゚チレン゜
ルビタン脂肪酞゚ステル、ゞアルキルスルホコハ
ク酞塩、アルキルトリメチルアンモニりムクロリ
ドなどが挙げられる。 本発明化合物の陀草剀ずしおの䜿甚量は通垞有
効成分ずしおアヌル圓り1.0〜20.0が奜適であ
るが、必ずしもこの範囲に限定されるものでな
く、埌述のように䜿甚堎面、斜甚方法、時期、適
甚䜜物、その他の条件においお適圓な量を䜿甚し
うる。 〓〓〓〓〓
本発明化合物の殺草䜜甚は、単に既存の薬剀に
比范しお匷力であるばかりでなく、極めお特城的
である。すなわち、これらは少くずも畑地におい
おは雑草皮子の発芜時のみ䜜甚しお、その発芜を
匷く抑制するが、発芜埌の雑草には党く䜜甚しな
い。このこずは発芜深床が異なる有甚䜜物の皮子
には安党であり、雑草のみを枯殺するこずが可胜
であり、さらに䜜物の移怍埌に凊理を行うこずに
よ぀おも遞択的に雑草のみの発生を抑制するこず
ができる。 本発明化合物の構造䞭には、既存の公知プノ
キシカルボン酞系陀草剀およびN1−アシルスル
フアニルアミド類あるいはスルフアニリル尿玠類
陀草剀に類䌌する郚分があるが、殺草特性におい
おはこれらず党く趣きを異にするものである。こ
の事実はこれら既存陀草剀を察照ずしお行぀た埌
述の詊隓䟋によ぀お、きわめお顕著な特性におけ
る差異ずしお確認された。 本発明化合物は、殺草掻性が匷力であり、した
が぀お少量の斜甚によ぀お充分な効果を䜎薬害で
期埅できる。 このようにしお本化合物は非蟲耕地、山林など
の非遞択性陀草剀ずしおはもちろん、蟲耕地甚の
遞択性陀草剀ずしお、有甚䜜物の播皮前あるいは
播皮埌、移怍前あるいは移怍埌の土壌凊理甚ずし
お、畑地あるいは氎田においお任意にその殺草掻
性を発揮させるこずができる。 本発明化合物を陀草剀ずしお䜿甚する堎合に
は、その䜿甚目的ずくに陀去しようずする雑草の
皮類、斜甚する畑地たたは氎田における有甚䜜物
の䜜付、栜培、䜜型など状況に応じお最適の化合
物の遞定ないし組合せがなされる。この最適化合
物の遞定ないし組合せは埌述の実斜䟋における詳
现な開瀺を勘案しお、それぞれ適宜実行するこず
が可胜である。 以䞋、本発明を、化合物合成䟋、補剀䟋および
詊隓䟋によ぀お、より詳现に説明する。 合成䟋  −−メチル−−クロルプノキシプ
ロピオン酞4.0、0.018モルず塩化チオニル
4.4、0.037モルずの混合物を90〜110℃で
時間還流させたのち倜攟眮する。この反応液か
ら過剰の塩化チオニルを枛圧留去した液䞭に、
N1−メトキシカルボニルスルフアニルアミド
4.0、0.032モルのピリゞン26.0mlの溶液
を15〜20℃に保ちながら玄分間を芁しお滎䞋す
る。 この反応混合物を20〜30℃で玄1.5時間撹拌し
たのち、35塩酞31.6ず氎32mlずの混
液を泚入しおPHを玄に調敎する。 その結果、混合液䞭に生じる粘皠物を傟瀉によ
り分離し、皀氎酞化ナトリりム氎溶液䞭に溶解さ
せたのち、玄20の塩酞を加えお析出する粗結晶
を取する。 この粗結晶をベンれンから再結晶させおN1−
メトキシカルボニル−N4−〔−−メチル−
−クロルプノキシプロピオニル〕スルフア
ニルアミド化合物No.を埗る粉末、収量
5.7、収率71.6。融点86〜87℃。 以䞋同様にしお次の第衚に挙げた化合物No.
ないしを埗た。これらを氎溶液䞭で氎酞化ナト
リりムたたは氎酞化カリりムを䜜甚させれば、こ
れらのN1−塩が容易に埗られる。 合成䟋  −メチル−−クロルプノキシ酢酞ク
ロリド10.98、0.048モルをN1−アセチルス
ルフアニルアミド9.64、0.048モルのピリ
ゞン95ml溶液に滎䞋し、50〜75℃で玄30分間
撹拌䞋に反応させたのち、ピリゞンを枛圧留去す
る。 残留物に氎100mlを投入しおスラリヌ化し、35
塩酞でPHに調敎し、析出する粗結晶を取す
る。 この粗結晶をアセトン300mlず氎140ml
ずの混液䞭に混合し、10氎酞化ナトリりムを滎
䞋しお溶解したのち、少量の脱色炭を加えお過
した母液を35塩酞にお䞭和し、析出する結晶を
取しおN1−アセチル−N4−−メチル−−
クロルプノキシアセチルスルフアニルアミド
化合物No.を埗る収量11.84、収率60.24
、小葉片状。融点253〜255℃。 〓〓〓〓〓
The present invention provides N 1 -methoxycarbonyl-N 4 -[2-
(2-Methyl-4-chlorophenoxy)propionyl]sulfanilamide, N1 -methoxycarbonyl- N4- (3,5-dichlorophenoxy)acetylsulfanilamide, N1 -methoxycarbonyl- N4- (3,5-dimethylphenoxy)acetylsulfanilamide, N1 -methoxycarbonyl- N4- (4-nitrophenoxy)acetylsulfanilamide, N1 -methoxycarbonyl- N4- (3-nitrophenoxy) Acetyl sulfanilamide, N 1 -methoxycarbonyl-N 4 -
(2,4-dinitrophenoxy)acetylsulfanilamide and N1 -acetyl- N4- (2-methyl-4-chlorophenoxy)acetylsulfur
N4 -phenoxyalkanoylsulfanilamides selected from the group consisting of nilamides (),
The present invention also relates to a herbicide containing at least one of these N4 -phenoxyalkanoylsulfanilamides or water-soluble metal salts thereof as an active ingredient. Compounds of the above formula are, for example, the corresponding phenoxyalkanoyl derivatives ()
When X is a halogen, the reaction is carried out in an inert organic solvent with a salt forming agent or a hydrogen halide scavenger, specifically an inorganic or hydrogen halide scavenger. It proceeds by contacting in the presence of an organic base. Examples of the phenoxyalkanoyl halides in () include 3-nitrophenoxyacetic acid, 4-nitrophenoxyacetic acid, and
-Nitrophenoxyacetic acid, 2,4-dinitrophenoxyacetic acid, 3,5-dichlorophenoxyacetic acid,
3,5-dimethylphenoxyacetic acid, 2-methyl-
Examples include chloride or bromide of 4-chlorophenoxyacetic acid and 2-methyl-4-chlorophenoxypropionic acid. Examples of the sulfanilamide () include N 1 -methoxycarbonylsulfanilamide and N 1 -acetylsulfanilamide. Examples of salt forming agents include sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium amide, sodium alkoxide, and the like; examples of hydrogen chloride scavengers include pyridine and triethylamine. Examples of the inert organic solvent include aromatic hydrocarbons such as benzene and toluene, dioxane, tetrahydrofuran, diethyl ether, pyridine, dimethylformamide, and dimethyl sulfoxide. The use of a solvent that also functions as the hydrogen chloride scavenger, such as pyridine, is convenient for simplifying the manufacturing process. The reaction is usually carried out at room temperature or slightly warmed, but in some cases, the mixture of the sulfanilamide and the solvent in () is cooled, and the acid halide in () is added to it or the solution thereof is added. A method such as dripping may also be used. Thereafter, the reaction is allowed to proceed under desired conditions, and the liquid properties are adjusted to obtain the optimum yield to complete the reaction. In addition, if the physical properties of the starting material and the product are acceptable, for example, if the melting point of the product is sufficiently higher than the melting points of both starting materials and both are highly stable against heat, phenoxyacetic acid, phenoxypropionyl The target substance can also be directly obtained by melting the free carboxylic acid together with the sulfanilamide under reduced pressure without converting the acid into a halide. The compound () obtained by the above method is recrystallized from a suitable solvent, such as aqueous methanol, or purified by chromatography. Alternatively, the obtained compound can be dissolved in water and treated with an alkali metal hydroxide or an alkaline earth metal to form a metal salt thereof. When the compounds () of the present invention are used as herbicides, they are usually diluted with a liquid or solid carrier that is inert to these compounds, and if necessary, a suitable auxiliary agent such as a surfactant is added thereto. emulsion,
It is used in the form of powder, wettable powder, granules, etc. Further, if necessary, other active ingredients may be mixed in for use. Liquid carriers used in the present invention include various organic solvents such as hydrocarbons such as kerosene, benzene, and xylene, halogenated hydrocarbons such as chlorobenzene and dichloroethylene, alcohols, and ketones such as acetone. Solid carriers include bentonite, kaolin, clay, talc, acid clay, diatomaceous earth,
Examples include silica sand, finely powdered silica, and calcium carbonate. Examples of the surfactant include alkylbenzenesulfonates, ligninsulfonates, higher alcohol sulfates, polyoxyethylene sorbitan fatty acid esters, dialkylsulfosuccinates, alkyltrimethylammonium chlorides, and the like. The amount of the compound of the present invention to be used as a herbicide is usually 1.0 to 20.0 g per are as the active ingredient, but it is not necessarily limited to this range, and as described below, the use situation, application method, timing, etc. It can be used in an appropriate amount depending on the crop to which it is applied and other conditions. 〓〓〓〓〓
The herbicidal action of the compounds of the present invention is not only more powerful than existing drugs, but also very unique. That is, at least in fields, these act only during the germination of weed seeds and strongly suppress the germination, but they do not act at all on weeds after germination. This is safe for seeds of useful crops that have different germination depths, and it is possible to kill only weeds.Furthermore, by performing treatment after transplanting crops, it is possible to selectively prevent the emergence of only weeds. Can be suppressed. The structure of the compound of the present invention has parts similar to existing known phenoxycarboxylic acid herbicides and N 1 -acylsulfanilamide or sulfanylylurea herbicides, but their herbicidal properties are different from those of these herbicides. It has a completely different taste. This fact was confirmed as a very significant difference in properties by the test examples described below in which these existing herbicides were used as controls. The compounds of the present invention have strong herbicidal activity, and therefore, sufficient effects can be expected with low chemical damage even when applied in small amounts. In this way, this compound can be used not only as a non-selective herbicide for non-agricultural land and forests, but also as a selective herbicide for agricultural land, for soil treatment before or after sowing useful crops, before or after transplantation. For use, its herbicidal activity can be exerted arbitrarily in upland fields or paddy fields. When using the compound of the present invention as a herbicide, the optimum compound should be selected depending on the purpose of use, especially the type of weeds to be removed, and the planting, cultivation, and cropping type of useful crops in the fields or paddy fields to which it will be applied. or combinations are made. The selection or combination of optimal compounds can be carried out as appropriate, taking into consideration the detailed disclosure in the Examples below. Hereinafter, the present invention will be explained in more detail using compound synthesis examples, formulation examples, and test examples. Synthesis Example 1 A mixture of 1-(2-methyl-4-chlorophenoxy)propionic acid (4.0 g, 0.018 mol) and thionyl chloride (4.4 g, 0.037 mol) was mixed at 90-110°C with 3
After refluxing for a while, leave it overnight. Excess thionyl chloride was distilled off under reduced pressure from this reaction solution, and in the solution,
A solution of N 1 -methoxycarbonylsulfanilamide (4.0 g, 0.032 mol) in pyridine (26.0 ml) is added dropwise over about 3 minutes while maintaining the temperature at 15-20°C. The reaction mixture was stirred at 20-30°C for about 1.5 hours, and then a mixture of 35% hydrochloric acid (31.6 g) and water (32 ml) was added to adjust the pH to about 2. As a result, the viscous substance produced in the mixture is separated by decantation, dissolved in a dilute aqueous sodium hydroxide solution, and then about 20% hydrochloric acid is added to remove the precipitated crude crystals. This crude crystal is recrystallized from benzene to give N 1 −
Methoxycarbonyl-N 4 -[2-(2-methyl-
4-Chlorphenoxy)propionyl]sulfanilamide (compound No. 1) is obtained (powder, yield
5.7g, yield 71.6%). Melting point 86-87℃. Similarly, Compound No. 3 listed in Table 1 below
I got a score of 7. These N 1 -salts can be easily obtained by reacting these with sodium hydroxide or potassium hydroxide in an aqueous solution. Synthesis Example 2 (2-Methyl-4-chlorophenoxy)acetic acid chloride (10.98 g, 0.048 mol) was added dropwise to a solution of N 1 -acetylsulfanilamide (9.64 g, 0.048 mol) in pyridine (95 ml) to give a solution of 50 to 75 After reacting at ℃ for about 30 minutes with stirring, pyridine was distilled off under reduced pressure. Pour 100ml of water into the residue to make a slurry,
Adjust the pH to 2 with % hydrochloric acid and collect the precipitated crude crystals. Add this crude crystal to acetone (300ml) and water (140ml).
10% sodium hydroxide was added dropwise to dissolve it, and a small amount of decolorizing charcoal was added.The filtered mother liquor was neutralized with 35% hydrochloric acid, the precipitated crystals were removed, and N 1 -acetyl-N 4 -(2-methyl-4-
Chlorphenoxy) acetylsulfanilamide (compound No. 2) was obtained (yield: 11.84 g, yield: 60.24
%, lobular). Melting point 253-255℃. 〓〓〓〓〓

【衚】 補剀䟋  氎和剀 本発明化合物50郚、゜ルポヌル東邊化孊工
業、商品名郚、ルノツクス東邊化孊工
業、商品名郚、カヌプレツクス80シオ
ノギ補薬、商品名15郚およびカオリン27郚を
粉砕混和しお有効成分50を含有する氎和剀を
埗る。  粒剀 本発明化合物郚、リグニンスルホン酞カル
シりム郚、ベントナむト30郚およびクレヌ60
郚を粉砕混和し氎を加え緎合しお造粒したの
ち、也燥しお有効成分を含有する粒剀を埗
る。 詊隓䟋 畑状態 以䞋の䟋〜における発芜前および発芜埌の
凊理は次の方法に埓぀お行぀た。 (1) 発芜前凊理発芜抑制掻性詊隓ずその評
䟡 被隓怍物の皮子25粒を砂壌土を充填した盎埄
cmのポリ゚チレンカツプに皮類別に播皮し
た。 播皮埌䟛詊化合物の氎性懞濁液化合物アセ
トン溶液、展着剀ずしおツむヌン20、100ppm
盞圓を䜿甚スプレヌにより土壌衚面に散垃
し、ただちに玄mmの厚さの芆土を行぀た。な
お、垌釈氎量はアヌル圓り10ずなるように調
補した。 管理は枩床25℃、自然日照の枩宀内で行ない
凊理埌週間埌に芳察した結果を次の段階評
䟡以䞋の詊隓においお共通によ぀お衚瀺し
た。 枯死たたは未発芜 枯死寞前の状態 圱響倧 圱響小 わずかに圱響 圱響なし (2) 発芜埌凊理生育抑制掻性詊隓 被隓怍物の播皮埌10日目の幌怍物に発芜前凊
理ず同様に、䟛詊化合物による凊理を行぀た。
管理、凊理埌週間目の芳察および評䟡も同様
に行぀た。 䟋  結果を第衚に総括する。この結果より本発明
化合物が雑草の発芜を匷力に抑制する掻性を有す
るこずが認められる。これは同䞀雑草に察する発
芜埌の生育抑制掻性ずは、きわめお察照的なもの
であるこずが瀺されおいる。 さらに具䜓的に蚀えば、本発明化合物は生育䞭
の有甚䜜物の移怍前たたは生育䞭に甚いるこずに
よ぀お、䜜物の生育に圱響を䞎えるこずなく、以
埌に発芜する雑草のみを制埡出来るこずが明らか
〓〓〓〓〓
にな぀た。
[Table] Formulation Example 1 Wettable powder: 50 parts of the compound of the present invention, 5 parts of Solpol (Toho Chemical Industries, trade name), 3 parts of Lunox (Toho Chemical Industries, trade name), Carplex #80 (Shionogi Pharmaceuticals, trade name) 15 parts and 27 parts of kaolin are ground and mixed to obtain a wettable powder containing 50% of the active ingredient. 2 Granules: 5 parts of the compound of the present invention, 5 parts of calcium lignosulfonate, 30 parts of bentonite, and 60 parts of clay
After pulverizing, mixing, adding water and kneading to granulate, the mixture is dried to obtain granules containing 5% of the active ingredient. Test Example (Field Condition) Pre-germination and post-germination treatments in Examples 1 to 3 below were carried out in accordance with the following methods. (1) Pre-germination treatment (germination inhibitory activity) test and its evaluation: 25 seeds of test plants were sown according to type into polyethylene cups 9 cm in diameter filled with sandy loam. After seeding, an aqueous suspension of the test compound (compound acetone solution, Tween 20 as a spreading agent, 100 ppm
It was applied to the soil surface using a sprayer and immediately covered with soil to a thickness of about 5 mm. The amount of dilution water was adjusted to 10 per are. Control was carried out in a greenhouse with natural sunlight at a temperature of 25°C, and the results observed 3 weeks after treatment were expressed using the following 6-level evaluation (common to the following tests). 5: Dead or non-germinated 4: On the verge of withering 3: Large effect 2: Small effect 1: Slightly affected 0: No effect (2) Post-emergence treatment (growth inhibition activity) test: 10 days after sowing of test plants The seedlings were treated with the test compound in the same manner as the pre-germination treatment.
Management, observation and evaluation 3 weeks after treatment were performed in the same manner. Example 1 The results are summarized in Table 2. These results demonstrate that the compound of the present invention has the activity of strongly inhibiting weed germination. This has been shown to be in sharp contrast to the post-emergence growth inhibitory activity against the same weed. More specifically, by using the compounds of the present invention before transplanting or during the growing of useful crops, it is possible to control only weeds that will germinate later on without affecting the growth of the crops. Obviously〓〓〓〓〓
It became.

【衚】 第衚には、本発明化合物がその構造の䞀郚に
察照化合物の構造に類䌌する郚分を含んでいるに
もかかわらず、その利甚面における殺草掻性にお
いお顕著な差が珟われおいるこずが瀺されおい
る。 このこずから、本発明化合物が凊理可胜時期の
点では制限を受けるものの畑地に限぀おいえば、
移怍埌たたは発芜埌の䜜物の凊理に関しおはきわ
めお有甚であるこずが刀る。 たた、察照化合物が発芜埌に䜜甚するものであ
り、あるいは、広葉雑草のみに有効であるのに察
しお、本発明化合物は発芜前に限りむネ科、広葉
雑草ずもに有効であるこずが瀺されおいる。 䟋  前蚘(2)の発芜埌凊理方法に埓぀お播皮埌の有甚
䜜物に察する圱響ず、共生雑草の発芜抑制掻性ず
を察比しお次頁の第衚に総括する結果を埗た。 すなわち、本発明化合物矀はいずれも播皮埌凊
理によ぀お、畑地に発生する䞻芁な雑草草皮に察
しお匷い発芜抑制ないし殺草効果を瀺し、トりモ
ロコシ、ダむズに察しおは、すべお圱響を䞎えな
か぀た。 このうち、化合物No.、、およびはコム
ギに察し、No.、、、およびはキナりリ
に察し、たたNo.はナタネに察しお圱響を䞎えな
か぀た。 䞀方察照化合物のうちおよびは、殺草ない
し発芜抑制掻性が認められたが、有甚䜜物のいず
れに察しおも著しい圱響があり、たたその他
、およびは䞡者に察しお共に䞍掻性で
あ぀た。 〓〓〓〓〓
[Table] Table 2 shows that although the compound of the present invention contains a part of its structure that is similar to that of the control compound, there is a significant difference in herbicidal activity when used. It is shown that there is. For this reason, although there are restrictions on the time when the compounds of the present invention can be treated, as far as farmland is concerned,
It proves to be extremely useful for the treatment of crops after transplantation or post-emergence. Furthermore, whereas the control compound acts after germination or is effective only against broad-leaved weeds, the compound of the present invention has been shown to be effective against both grass and broad-leaved weeds only before germination. . Example 2 In accordance with the post-emergence treatment method described in (2) above, the effects on useful crops after sowing and the germination-suppressing activity of symbiotic weeds were compared, and the results summarized in Table 3 on the next page were obtained. In other words, all of the compounds of the present invention exhibit strong germination-suppressing or herbicidal effects against major weed species occurring in fields through post-sowing treatment, and all have no effect on corn and soybean. Nakatsuta. Of these, compounds Nos. 1, 2, 5 and 6 had no effect on wheat, Nos. 1, 2, 3, 5 and 6 had no effect on cucumber, and No. 5 had no effect on rapeseed. On the other hand, among the control compounds A and B, herbicidal or germination inhibiting activity was observed, but they had a significant effect on all useful crops, and the others (C, D, and E) had no effect on both. It was inactive. 〓〓〓〓〓

【衚】 䟋  䟋に準じ、有甚䜜物に察する本発明化合物の
圱響を、それぞれ発芜前、発芜埌凊理によ぀お詊
隓し、次の第衚に総括する結果を埗た。
[Table] Example 3 According to Example 1, the effects of the compounds of the present invention on useful crops were tested by pre-emergence and post-emergence treatments, and the results are summarized in Table 4 below.

【衚】 ここで、化合物No.が発芜前凊理においお、ト
りモロコシ、゜ルガム、コムギおよびビヌトに察
し、たた化合物No.がコムギに察しおかなりの圱
響を䞎えたものの、同No.は発芜前および発芜埌
いずれにおいおも実甚䞊問題ずなる皋の圱響を䞎
えず、党化合物ずも発芜埌においおは䜜物に䜕等
の圱響を䞎えるものでないこずが確認された。 察照ずしお甚いたリニナロン(F)はトりモロコシ
の発芜前凊理を陀き、䟛詊䜜物のすべおに察し
お、その生育を阻害した。 䟋  本䟋は次の詊隓法に埓぀お行぀た。 (3) 土壌混和凊理詊隓 バツト40×40に砂壌土を填め、所定
量の䟛詊化合物を、混和深床がcmになるよう
に混和を行぀たのち、䟛詊怍物を播皮した。 管理、芳察凊理埌週間目、および評䟡
は前蚘(1)、(2)に準じお行い次頁の第衚に総括
する結果を埗た。 〓〓〓〓〓
[Table] Here, Compound No. 1 had a considerable effect on corn, sorghum, wheat, and beet in the pre-germination treatment, and Compound No. 4 had a considerable effect on wheat, but Compound No. 3 had a considerable effect on wheat. It was confirmed that there was no effect to the extent that it would be a practical problem either before or after germination, and it was confirmed that none of the compounds had any effect on the crops after germination. Linyuron (F), which was used as a control, inhibited the growth of all the tested crops, except for the pre-emergence treatment of maize. Example 4 This example was conducted according to the following test method. (3) Soil mixing treatment test: A vat (40 m x 40 m) was filled with sandy loam soil, a predetermined amount of the test compound was mixed in to a mixing depth of 5 cm, and then the test plants were sown. Management, observation (3 weeks after treatment), and evaluation were performed according to (1) and (2) above, and the results are summarized in Table 5 on the next page. 〓〓〓〓〓

【衚】 第衚より、本発明化合物を土壌混和凊理に
䜿甚しお凊理局の深さを拡倧した堎合においお
も、雑草ず有甚䜜甚ずの間に高い遞択性が維持
可胜である特城を有しおいるこずが刀る。 殺草スペクトラムに関しお、化合物No.はア
オビナを含め、すべおの䟛詊雑草に圱響を䞎
え、化合物No.、およびはむヌビ゚、メヒ
シバ、むヌタデに察しおかなりの圱響を䞎え、
薬量さえ充分であれば、完党枯殺たたは枯殺に
近い圱響を䞎える。 有甚䜜物に察する圱響に関しおいえば、トり
モロコシに察しお、化合物No.を陀いおは、い
ずれの化合物も薬害を瀺さなか぀た。ダむズに
察しおはいずれの化合物も薬害を瀺さなか぀
た。コムギに察しおは化合物No.が党く無害で
ありたたトマトに察しおは化合物No.、およ
びの化合物は実甚䞊問題ずなる皋床の薬害
を瀺さなか぀た。 䞊蚘の結果から化合物No.はトりモロコシ、
コムギ、ダむズ、トマト、キナりリに化合物No.
およびはトりモロコシ、ダむズに、たた化
合物No.はダむズに察する有甚性が認められ
た。 䟋  本䟋は次の詊隓法に埓぀お行぀た。 (4) むネ詊隓ポツト法 5000ワグネルポツトに氎田土壌を填め、
湛氎前雑草皮子を播皮し、その雑草の発芜前に
所定量の䟛詊化合物氎性懞濁液を滎䞋凊理し
た。 その盎埌ポツト圓り株のむネを定怍した。 管理は前蚘(1)〜(3)に準じお行い、凊理ケ月
埌に怍物の重量を枬定し、無凊理怍物重量に察
する割合により衚瀺し、次の第衚に瀺
す結果を埗た。
[Table] Table 5 shows that even when the compound of the present invention is used in soil mixing treatment to expand the depth of the treatment layer, it has the characteristic that high selectivity between weeds and beneficial effects can be maintained. I can see that you are doing it. Regarding the herbicidal spectrum, Compound No. 1 affected all tested weeds, including Japanese grasshopper, while Compounds No. 3, 4, and 6 had a considerable effect on Japanese grasshopper, Japanese knotweed, and Japanese knotweed.
If the dose is sufficient, it can cause complete or near-killing effects. Regarding the effects on useful crops, none of the compounds showed any phytotoxicity to corn except for Compound No. 1. None of the compounds showed any toxicity to soybean. Compound No. 6 was completely harmless to wheat, and Compounds No. 3, 4, and 6 did not cause any practical damage to tomatoes. From the above results, compound No. 6 is corn,
Compound No. 1 is found in wheat, soybeans, tomatoes, and cucumbers.
Compound No. 3 and 4 were found to be useful for corn and soybeans, and Compound No. 1 was found to be useful for soybeans. Example 5 This example was conducted according to the following test method. (4) Rice test (pot) method: Fill a/5000 Wagner pot with paddy soil,
Pre-flooded weed seeds were sown, and a predetermined amount of an aqueous suspension of the test compound was added dropwise to the weeds before germination. Immediately thereafter, two rice plants per pot were planted. Management was carried out according to (1) to (3) above, and the weight of the plants was measured one month after the treatment and expressed as a percentage (%) of the untreated plant weight, and the results shown in Table 6 below were obtained. .

【衚】 〓〓〓〓〓
[Table] 〓〓〓〓〓

【衚】 前衚で明らかなように、湛氎条件䞋においお
凡おの䟛詊化合物はおよび10の
薬量で氎田䞻芁雑草のタむヌビ゚、カダツリグ
サおよびその他の広葉雑草の発生を抑制する。
ずくに化合物No.はの薬量で氎田重芁
雑草のほがすべおに察しおその発生を完党に抑
制する。 たた䟛詊化合物のむネに察する安党性では化
合物No.に軜床の圱響が認められたが、その他
の化合物に぀いおは䜕等の圱響も認められなか
぀た。 䟋  (5) 氎皲詊隓圃堎法発芜前凊理 野倖圃堎に蚭眮した50×50×50cmのコンクリ
ヌトポツトに氎田土壌砂壌土を぀め、cm
の湛氎を行぀た。そこにポツト圓り株のむネ
2.5葉期を定怍し、さらに氎田重芁倚幎生雑
草の地䞋茎たたは塊茎をうめこみ、さらに幎
生氎田雑草を播皮した。その盎埌、所定量の䟛
詊化合物氎性懞濁液を滎䞋しお凊理した。 自然日照条件䞋、平均気枩17〜28℃で30日間
攟眮したのち、むネ、䞀幎生雑草自然発生
および倚幎生雑草を抜き取り、分別秀量しお氎
田条件における雑草に察する防陀効果ず、むネ
に察する圱響を芳察評䟡し、無凊理区ず察比し
お次の第衚に総括する結果を埗た数字は残
草量を衚わす。
[Table] As is clear from the previous table, under flooded conditions, all the test compounds suppressed the emergence of major weeds in paddy fields such as Japanese millet, Cyperus japonica, and other broad-leaved weeds at dosages of 5 g/a and 10 g/a. do.
In particular, Compound No. 1 completely inhibits the growth of almost all important weeds in paddy fields at a dosage of 5 g/a. Regarding the safety of the test compounds on rice, a slight effect was observed on Compound No. 1, but no effects were observed on the other compounds. Example 5 (5) Paddy rice test (field) method: Pre-germination treatment A 50 x 50 x 50 cm concrete pot set up in an outdoor field is filled with paddy soil (sandy loam) and 5 cm
The area was flooded. Four rice plants (2.5 leaf stage) per pot were planted there, underground stems or tubers of important perennial weeds in paddy fields were embedded, and annual paddy weeds were sown. Immediately thereafter, a predetermined amount of an aqueous suspension of the test compound was added dropwise for treatment. After being left for 30 days under natural sunlight conditions at an average temperature of 17-28℃, rice and annual weeds (naturally occurring)
We pulled out and perennial weeds, separated them, and weighed them to observe and evaluate the weed control effect and impact on rice under paddy field conditions, and obtained the results summarized in Table 7 below in comparison with the untreated plot. (represents grass amount%).

【衚】 〓〓〓〓〓
[Table] 〓〓〓〓〓

【衚】 前衚で明らかなように、化合物No.および
はそれぞれの薬量においお、䟛詊䞀幎生雑草の
発芜を完党に抑制した。さらに同No.は防陀の
困難な倚幎生雑草に察しお、珟圚垂販䞭の倚幎
生雑草甚陀草剀である察照薬ずクログワむに
察する効果では劣るものの、では完党防陀で
きないミズガダツリおよびヒルムシロに察しお
も高い効果を瀺した。この堎合むネに察する圱
響はよりも著しく䜎か぀た。䞀方、我囜の氎
田甚初期陀草剀ずしお広く甚いられおいる察照
薬は倚幎生雑草に察しお効果を瀺さなか぀
た。 混合剀である察照薬がこの凊理時期におい
おむネに察しお匷い薬害を瀺すのに察し、化合
物No.は単味剀でありながら薬害が軜埮で氎田
甚陀草剀ずしお優れた特性を有しおいるこずが
認められた。 䟋  (6) むネ詊隓ポツト法発芜埌凊理による生
育抑制効果 5000ワグネルポツトに氎田土壌を぀め、
湛氎前䞀幎生雑草の皮子を播皮、か぀倚幎生雑
草の塊茎を怍蟌み、その盎埌ポツト圓り株の
むネを定怍しお湛氎した。 その埌、むネおよび雑草が䞋蚘の葉什に達し
た時葉期に所定量の䟛詊化合物を適䞋しお
凊理した。 むネ3.8葉 ミズガダツリ葉15cm クログワむ葉cm りリカワ葉cm タむヌビ゚1.5葉cm 管理は前蚘(4)ず同様に行ない、凊理ケ月埌
にむネに察する圱響ならびに雑草に察する効果
を枬定し、次の第衚に瀺す結果を埗た。
[Table] As is clear from the previous table, compounds No. 1 and 4
At each dose, germination of the annual weeds tested was completely suppressed. Furthermore, No. 1 is less effective against perennial weeds that are difficult to control than the control drug H, which is a perennial weed herbicide currently on the market, against Japanese black grubs. It was highly effective. In this case, the effect on rice was significantly lower than that of H. On the other hand, a control drug widely used as an initial herbicide for paddy fields in Japan had no effect on perennial weeds. Comparative drug H, which is a mixture, shows strong phytotoxicity to rice at this treatment stage, whereas Compound No. 1, although a single agent, has only slight phytotoxicity and has excellent properties as a herbicide for paddy fields. It was recognized that Example 6 (6) Rice test (pot) method (growth inhibition effect by post-germination treatment): Pack paddy soil into a/5000 Wagner pot,
Before flooding, seeds of annual weeds were sown and tubers of perennial weeds were planted. Immediately thereafter, two rice plants per pot were planted and flooded. Thereafter, when the rice and weeds reached the following leaf stage (leaf stage), a predetermined amount of the test compound was applied and treated. Rice: 3.8 leaves Cyperus japonica: 3 leaves (15cm) Black-capped cypress: 5 leaves (5cm) Urikawa: 4 leaves (5cm) Japanese millet: 1.5 leaves (8cm) Management was carried out in the same manner as in (4) above, and the effect on rice after 1 month of treatment The effects on weeds were also measured, and the results shown in Table 8 below were obtained.

【衚】 前衚によ぀お明らかなように、化合物No.は
10の薬量においお、䞀幎生広葉雑草を完
党に抑制し、倚幎生雑草䞭マツバむ、ヒルムシ
ロに䞭等床の抑制効果を瀺した。これに察し
お、察照薬A′およびE′は䞀幎生および倚幎生
雑草の䞡者に殆んど圱響を䞎えなか぀た。 このように化合物No.は湛氎条件䞋では、か
なり葉期の進んだ広葉雑草および倚幎生雑草に
〓〓〓〓〓
察しおも有効であり、氎田陀草剀ずしおすぐれ
た特性を有しおいるこずが認められた。 〓〓〓〓〓
[Table] As is clear from the previous table, compound No. 1 is
At a dosage of 10 g/a, it completely suppressed annual broad-leaved weeds and showed a moderate suppressive effect on perennial weeds such as pine snail and cypress. In contrast, control drugs A' and E' had little effect on both annual and perennial weeds. In this way, under flooded conditions, Compound No. 1 is effective against broad-leaved weeds and perennial weeds with considerably advanced leaf stages.
It was also found that it is effective against herbicides and has excellent properties as a paddy herbicide. 〓〓〓〓〓

Claims (1)

【特蚱請求の範囲】  N1−メトキシカルボニル−N4−−−
メチル−−クロルプノキシプロピオニル
スルフアニルアミド、N1−メトキシカルボニル
−N4−・−ゞクロルプノキシアセチル
スルフアニルアミド、N1−メトキシカルボニル
−N4−・−ゞメチルプノキシアセチル
スルフアニルアミド、N1−メトキシカルボニル
−N4−−ニトロプノキシアセチルスルフ
アニルアミド、N1−メトキシカルボニル−N4−
−ニトロプノキシアセチルスルフアニル
アミド、N1−メトキシカルボニル−N4−・
−ゞニトロプノキシアセチルスルフアニルア
ミドおよびN1−アセチル−N4−−メチル−
−クロルプノキシアセチルスルフアニルアミ
ドよりなる矀より遞ばれたN4−プノキシアル
カノむルスルフアニルアミド類。  N1−メトキシカルボニル−N4−−−
メチル−−クロルプノキシプロピオニル
スルフアニルアミド、N1−メトキシカルボニル
−N4−・−ゞクロルプノキシアセチル
スルフアニルアミド、N1−メトキシカルボニル
−N4−・−ゞメチルプノキシアセチル
スルフアニルアミド、N1−メトキシカルボニル
−N4−−ニトロプノキシアセチルスルフ
アニルアミド、N1−メトキシカルボニル−N4−
−ニトロプノキシアセチルスルフアニル
アミド、N1−メトキシカルボニル−N4−・
−ゞニトロプノキシアセチルスルフアニルア
ミドおよびN1−アセチル−N4−−メチル−
−クロルプノキシアセチルスルフアニルアミ
ドよりなる矀より遞ばれたN4−プノキシアル
カノむルスルフアニルアミド類たたはその氎溶性
金属塩のうち少なくずも個を有効成分ずしお含
有する陀草剀。
[Claims] 1 N 1 -methoxycarbonyl-N 4 -[2-(2-
Methyl-4-chlorophenoxy)propionyl]
Sulfanilamide, N1 -methoxycarbonyl- N4- (3,5-dichlorophenoxy)acetylsulfanilamide, N1 -methoxycarbonyl- N4- (3,5-dimethylphenoxy)acetyl Sulfanilamide, N1 -methoxycarbonyl- N4- (4-nitrophenoxy)acetylsulfanilamide, N1 -methoxycarbonyl- N4-
(3-nitrophenoxy)acetylsulfanilamide, N1 -methoxycarbonyl- N4- (2.4
-dinitrophenoxy)acetylsulfanilamide and N1 -acetyl- N4- (2-methyl-4
-N4 -phenoxyalkanoylsulfanilamide selected from the group consisting of -chlorophenoxy)acetylsulfanilamide. 2 N 1 -Methoxycarbonyl-N 4 -[2-(2-
Methyl-4-chlorophenoxy)propionyl]
Sulfanilamide, N1 -methoxycarbonyl- N4- (3,5-dichlorophenoxy)acetylsulfanilamide, N1 -methoxycarbonyl- N4- (3,5-dimethylphenoxy)acetyl Sulfanilamide, N1 -methoxycarbonyl- N4- (4-nitrophenoxy)acetylsulfanilamide, N1 -methoxycarbonyl- N4-
(3-nitrophenoxy)acetylsulfanilamide, N1 -methoxycarbonyl- N4- (2.4
-dinitrophenoxy)acetylsulfanilamide and N1 -acetyl- N4- (2-methyl-4
A herbicide containing as an active ingredient at least one N 4 -phenoxyalkanoylsulfanilamide or a water-soluble metal salt thereof selected from the group consisting of -chlorophenoxy)acetylsulfanilamide.
JP13664880A 1980-09-29 1980-09-29 N4-phenoxyalkanoylsulfanilamide and herbicide Granted JPS5759855A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP13664880A JPS5759855A (en) 1980-09-29 1980-09-29 N4-phenoxyalkanoylsulfanilamide and herbicide

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP13664880A JPS5759855A (en) 1980-09-29 1980-09-29 N4-phenoxyalkanoylsulfanilamide and herbicide

Publications (2)

Publication Number Publication Date
JPS5759855A JPS5759855A (en) 1982-04-10
JPS6222981B2 true JPS6222981B2 (en) 1987-05-20

Family

ID=15180231

Family Applications (1)

Application Number Title Priority Date Filing Date
JP13664880A Granted JPS5759855A (en) 1980-09-29 1980-09-29 N4-phenoxyalkanoylsulfanilamide and herbicide

Country Status (1)

Country Link
JP (1) JPS5759855A (en)

Also Published As

Publication number Publication date
JPS5759855A (en) 1982-04-10

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