JPS6054954B2 - Diphenyl ether derivatives and herbicides containing diphenyl ether derivatives - Google Patents

Diphenyl ether derivatives and herbicides containing diphenyl ether derivatives

Info

Publication number
JPS6054954B2
JPS6054954B2 JP52089729A JP8972977A JPS6054954B2 JP S6054954 B2 JPS6054954 B2 JP S6054954B2 JP 52089729 A JP52089729 A JP 52089729A JP 8972977 A JP8972977 A JP 8972977A JP S6054954 B2 JPS6054954 B2 JP S6054954B2
Authority
JP
Japan
Prior art keywords
diphenyl ether
ether derivatives
nitrodiphenyl ether
mol
solution
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
JP52089729A
Other languages
Japanese (ja)
Other versions
JPS5424851A (en
Inventor
繁喜 長井
行 関岡
允章 竹中
正純 坂田
嘉夫 河口
斉治 高村
実 西村
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.)
Ube Corp
Original Assignee
Ube Industries 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 Ube Industries Ltd filed Critical Ube Industries Ltd
Priority to JP52089729A priority Critical patent/JPS6054954B2/en
Priority to GB787830523A priority patent/GB2001635B/en
Priority to DE19782833021 priority patent/DE2833021A1/en
Priority to NL7807967A priority patent/NL7807967A/en
Priority to IT26201/78A priority patent/IT1097782B/en
Priority to BR7804864A priority patent/BR7804864A/en
Priority to SU782646951A priority patent/SU843695A3/en
Priority to CA308,293A priority patent/CA1111062A/en
Priority to FR7822495A priority patent/FR2398728A1/en
Priority to US06/006,919 priority patent/US4213775A/en
Priority to PH22142A priority patent/PH15699A/en
Publication of JPS5424851A publication Critical patent/JPS5424851A/en
Publication of JPS6054954B2 publication Critical patent/JPS6054954B2/en
Expired legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52—Y being a hetero atom
    • C07C311/53—X and Y not being nitrogen atoms, e.g. N-sulfonylcarbamic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52—Y being a hetero atom
    • C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
    • C07C311/55—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to acyclic carbon atoms

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

【発明の詳細な説明】 この発明は、一般式 （ただし、式中Ｘはハロゲン原子を示し、ｎは１〜３の
整数を示し、Ｒは水素原子、低級アルコキシカルボニル
基、アセチル基、クロルアセチル基、Ｎ，Ｎ−ジメチル
カルバモイル基を示す。DETAILED DESCRIPTION OF THE INVENTION This invention is based on the general formula (wherein, group, N,N-dimethylcarbamoyl group.

）で表わされる新規なジフェニルエーテル誘導体を提供
し、またこの新規なジフェニルエーテル誘導体を有効成
分とする除草剤を提供するものである。ジフェニルエー
テル誘導体を有効成分とする除草剤は、古くから数多く
提案されており、市販されているものも少くなく、その
例としてＮＩＰ（有効成分：２″，４−ジクロロー４−
ニトロジフェニルエーテル）、ＣＮＰ（２″，４″，６
″−１・りクロロー４−ニトロジフェニルエーテル）、
ＴＯＰＥ（３″一メチルー４−ニトロジフェニルエーテ
ル）などの除草剤が挙げられる。), and also provides a herbicide containing this novel diphenyl ether derivative as an active ingredient. Many herbicides containing diphenyl ether derivatives as active ingredients have been proposed for a long time, and many are commercially available, such as NIP (active ingredient: 2'',4-dichloro-4-
nitrodiphenyl ether), CNP (2″, 4″, 6
″-1・richloro-4-nitrodiphenyl ether),
Examples include herbicides such as TOPE (3″-monomethyl-4-nitrodiphenyl ether).

これら従来知られているジフェニルエーテル系除草剤は
、一般に水田に発生する一年生イネ科雑草に対する土壌
処理能力には優れているが、諸雑草に対する茎葉処理能
力、あるいは一年生広葉雑草や多年生雑草に対する除草
効果が劣る、という共通の特質を有している。またこの
種の誘導体は、他の有機化合物の場合と同様に、置換基
の種類、数または位置などの相異による化学構造上の差
異に起因して、除草効果の有無、大小、遅速あるいは作
物に対する薬害の有無、などが予想外に異なる場合が多
い。この発明者らは、従来文献未載の産業上有用なジフ
ェニルエーテル誘導体を得ることを目的として、種々鋭
意研究を行つた。These conventionally known diphenyl ether herbicides have excellent soil treatment ability against annual gramineous weeds that generally occur in rice fields, but they have poor foliage treatment ability against various weeds or herbicidal effects against annual broad-leaved weeds and perennial weeds. They have a common characteristic of being inferior. In addition, as with other organic compounds, these derivatives differ in their chemical structure due to differences in the type, number, or position of substituents, depending on their herbicidal effect, size, slowness, or herbicidal effect on crops. In many cases, the presence or absence of drug-induced harm to other substances differs unexpectedly. The inventors have conducted various studies with the aim of obtaining industrially useful diphenyl ether derivatives that have not been previously described in literature.

その結果、一般式 （ただし、式中Ｘ，ｎおよびＲは、前記と同じ意味を有
する。As a result, the general formula (wherein X, n and R have the same meanings as above) is obtained.

）で表わされる、新規なジフェニルエーテル誘導体の合
成に成功し、さらにこの新規なジフェニルエーテル誘導
体は、諸雑草に対し”卓越した除草効果を有し、しかも
諸作物に対する薬害や、人蓄、魚貝類に対する毒性およ
び異臭なども全くないことを見い出し、この発明に到達
した。この発明におけるジフェニルエーテル誘導体は、
土壌に散布して発生前後の雑草を枯死させる能力、いわ
ゆる土壌処理能力と茎葉処理能力の両者を兼ね備えてお
り、その効果も水田および畑地に発生する一年生また多
年生のイネ科雑草、広葉雑草など広範囲の諸雑草に対し
有効である。), and this new diphenyl ether derivative has an excellent herbicidal effect on various weeds, and is free from chemical damage to various crops, human hoarding, and toxicity to fish and shellfish. The present invention was achieved by discovering that the diphenyl ether derivative in this invention has no foreign odor.
It has the ability to spray on the soil and kill weeds before and after they emerge, which is the so-called soil treatment ability and foliage treatment ability.It is effective against a wide range of annual and perennial grass weeds and broad-leaved weeds that occur in rice fields and fields. It is effective against various weeds.

従つて、この発明の除草剤は、水田においては田植前後
の初期型除草剤、あるいは多年生雑草、広葉雑草を対象
とした田植後１〜２週間後における中期型除草剤として
有効であり、また畑地においては作物の播種前後の土壌
処理型除草剤、あるいは果樹園、茶畑、桑畑、非農耕地
における諸雑草に対する茎葉処理型除草剤として使用に
供すことができる。またこの発明の除草剤は、従来公知
のジフェニルエーテル系除草剤では全く防除できなかつ
たナデシコ科の雑草に対しても、極めて高い除草活性を
示す、という特質も有している。第１表に、この発明に
おける新規ジフェニルエーテルの誘導体例を挙げる。Therefore, the herbicide of the present invention is effective as an early-stage herbicide before and after rice planting in rice fields, or as a mid-stage herbicide 1 to 2 weeks after rice planting targeting perennial weeds and broad-leaved weeds, and is also effective in rice fields. It can be used as a soil treatment herbicide before and after sowing crops, or as a foliar treatment herbicide against various weeds in orchards, tea fields, mulberry fields, and non-agricultural lands. The herbicide of the present invention also has the characteristic of exhibiting extremely high herbicidal activity against weeds of the Caryophyllaceae family, which have not been able to be controlled at all by conventionally known diphenyl ether herbicides. Table 1 lists examples of novel diphenyl ether derivatives in this invention.

なお、この発明における除草剤は、これらジフェニルエ
ーテルの誘導体の塩も有効成分として有用であり、その
代表的な塩として、７，４″，６″一トリクロロー３−
メトキシカルボニルアミノスルホニルー４−ニトロジフ
ェニルエーテルのナトリウム塩を化合物番号２５に、ま
た７，４″，−ジクロロー３−メトキシカルボニルアミ
ノスルホニルー４−ニトロジフェニルエーテルのナトリ
ウム塩を化合物番号３６に挙げこの発明におけるこれら
ジフェニルエーテル誘導体は、例えば次に示す各反応工
程によつて合成することができる。意味を有す。次に、
各工程の合成例を示す。In the herbicide of the present invention, salts of these diphenyl ether derivatives are also useful as active ingredients, and representative salts include 7,4'',6''-trichloro-3-
The sodium salt of methoxycarbonylaminosulfonyl-4-nitrodiphenyl ether is listed as compound number 25, and the sodium salt of 7,4'',-dichloro-3-methoxycarbonylaminosulfonyl-4-nitrodiphenyl ether is listed as compound number 36. The diphenyl ether derivative can be synthesized, for example, by the following reaction steps.It has a meaning.Next,
A synthesis example of each step is shown.

合成例１第１工程の合成例、 イソプロピルアルコール１．４１に、１−ニトロー２，
４−ジクロロベンゼン８６ｇ（０．４モル）とベンジル
メルカプタン５６ｇ（０．４５モル）を溶解させ、攪拌
下、水酸化カリウム３０ｇの水２０ｍ１とエタノール７
０ｍｔの混溶液を徐々に滴下し、滴下終了後水浴上で３
時間還流した。Synthesis Example 1 Synthesis example of the first step, 1.41 isopropyl alcohol, 1-nitro 2,
86 g (0.4 mol) of 4-dichlorobenzene and 56 g (0.45 mol) of benzyl mercaptan were dissolved, and while stirring, 30 g of potassium hydroxide, 20 ml of water and 7 ml of ethanol were dissolved.
Gradually drop 0 mt of the mixed solution, and after dropping, place on a water bath for 3 minutes.
Refluxed for an hour.

一夜放置後、結晶を枦集し、次いでエタノールと少量の
ベンゼン混合液から再結し、黄色プリズム状結晶のベン
ジルー２一ニトロー５−クロロフェニルスルフィド（融
点１３１〜１３４クＣ）を８７ｇ（収率７０％）得た。
合成例２第２工程の合成例、ジメチルアセトアミド３０
ｍ１に、２，４−ジクロロフェノール１６．３ｇ（０．
１モル）を溶解させた後、水酸化カリウム５．６ｇ（０
．１モル）を添加し、１２０℃に加熱攪拌し、水酸化カ
リウムを溶解させた。After standing overnight, the crystals were collected and then re-crystallized from a mixture of ethanol and a small amount of benzene to obtain 87 g of benzyl-2-nitro-5-chlorophenyl sulfide (melting point: 131-134 °C) in the form of yellow prisms (yield: 70 °C). %)Obtained.
Synthesis Example 2 Synthesis example of second step, dimethylacetamide 30
ml, 16.3 g of 2,4-dichlorophenol (0.
After dissolving 1 mole of potassium hydroxide, 5.6 g of potassium hydroxide (0
．． 1 mol) was added thereto, and the mixture was heated and stirred at 120°C to dissolve potassium hydroxide.

次いで放冷後、ベンジルー２−ニトロー５−クロロフェ
ニルスルフィド２８ｇ（０．１モル）を添加し、約１５
５℃で６時間加熱攪拌後、冷却し、水を添加して析出し
た油状物をベンゼンで抽出した。次いで、抽出物を希水
酸化ナトリウム水溶液および水で洗浄した後、硫酸ナト
リウムで乾燥し、ベンゼンを留去後、残留物をエタノー
ルから再結し、黄色粉末状結晶の２″，４″−ジクロロ
ー３−ベンジルメルカプトー４−ニトロジフェニルエー
テル（融点１０４〜１０５℃）を２７ｇ（収率６７％）
得た。Then, after cooling, 28 g (0.1 mol) of benzyl-2-nitro-5-chlorophenyl sulfide was added, and about 15
After heating and stirring at 5° C. for 6 hours, the mixture was cooled, water was added, and the precipitated oil was extracted with benzene. The extract was then washed with a dilute aqueous sodium hydroxide solution and water, dried over sodium sulfate, and after distilling off the benzene, the residue was recrystallized from ethanol to form yellow powdery crystals of 2'',4''-dichloromethane. 27 g (yield 67%) of 3-benzyl mercapto 4-nitrodiphenyl ether (melting point 104-105°C)
Obtained.

合成例３第３工程および第４工程の合成例、２″，４″
−ジクロロー３−ベンジルメルカプトー４−ニトロジフ
ェニルエーテル３３ｇ（０．００８モル）を、氷酢酸２
００ｍ１と水３０ｍＬの混合液に懸濁させ、攪拌下、約
１７Ｃにて塩素ガスを吹き込んだ後、常温で一夜放置し
た。次いで、内容物を水に注ぎ、析出した油状物をベン
ゼンで抽出した後、抽出物を水洗し、硫酸ナトリウムで
乾燥した後、溶媒を留去し、暗赤色油状物の２″，４″
−ジクロロー３一クロロスルホニルー４−ニトロジフエ
ニルエーテ次いでこれを、酢酸エチルエステルに溶解さ
せた後、アンモニアの飽和酢酸エチルエステル中に滴下
した。滴下終了後、常温で３紛間攪拌し、水を添加して
反応液を水洗し、次いで硫酸ナトリウムで乾燥した後、
溶媒を留去し残留物をエタノールから再結し、淡黄色粉
末状結晶の２″，４″−ジクロロー３−アミノスルホニ
ルー４−ニトロジフェニルエーテル（化合物番号８の化
合物：融点９５〜９８℃）を２２．７ｇ（収率７８％）
得た。合成例４第５工程の合成例、（１）２″，４″−
ジクロロー３−エトキシカルボニルアミノスルホニルー
４−ニトロジフェニルエーテル（化合物番号１０の化合
物）の合成、１．２５Ｗｔ％水酸化ナトリウム水溶液４
０ｍＬに、２″，４″−ジクロロー３−アミノスルホニ
ルー４一ニトロジフェニルエーテル３．６ｇ（０．０１
モル）を溶解させた後、攪拌下、約２５℃にてクロロギ
酸エチル３．６ｇ（０．０３３モル）と１０Ｗｔ％水酸
化ナトリウム水溶液を交互に滴下し、ＰＨを１０〜１１
に調整した。Synthesis Example 3 Synthesis example of 3rd step and 4th step, 2″, 4″
- 33 g (0.008 mol) of dichloro-3-benzylmercapto-4-nitrodiphenyl ether was mixed with 2 ml of glacial acetic acid.
The suspension was suspended in a mixed solution of 00ml and 30mL of water, chlorine gas was blown into the suspension at about 17C under stirring, and the suspension was left overnight at room temperature. Next, the contents were poured into water, the precipitated oil was extracted with benzene, the extract was washed with water, dried over sodium sulfate, the solvent was distilled off, and a dark red oily substance 2", 4"
-Dichloro-3-chlorosulfonyl-4-nitrodiphenyl ether This was then dissolved in ethyl acetate and then added dropwise into saturated ethyl acetate of ammonia. After the addition was completed, the mixture was stirred three times at room temperature, water was added and the reaction solution was washed with water, and then dried over sodium sulfate.
The solvent was distilled off and the residue was recrystallized from ethanol to give pale yellow powder crystals of 2'',4''-dichloro-3-aminosulfonyl-4-nitrodiphenyl ether (Compound No. 8: melting point 95-98°C). 22.7g (yield 78%)
Obtained. Synthesis Example 4 Synthesis example of the 5th step, (1) 2″, 4″-
Synthesis of dichloro-3-ethoxycarbonylaminosulfonyl-4-nitrodiphenyl ether (compound No. 10), 1.25 Wt% sodium hydroxide aqueous solution 4
To 0 mL, 3.6 g (0.01
After dissolving 3.6 g (0.033 mol) of ethyl chloroformate and a 10 wt% aqueous sodium hydroxide solution at about 25°C with stirring, the pH was adjusted to 10-11.
Adjusted to.

滴下終了後、３紛間攪拌し、次いで希塩酸水溶液を滴下
ＬＰＨを６．５に調整した後、不溶物を戸去した。次い
で、枦液を強塩酸酸性にし、析出した結晶を枦集し、乾
燥後、ベンゼンから再結し淡黄色プリズム状結晶の２″
，４″ージクロロー３−エトキシカルボニルアミノスル
ホニルー４−ニトロジフェニルエーテル（融点１３８〜
１４０℃）を２．５ｇ（収率５７％）得た。（２）２″
，４″−ジクロロー３−クロロアセチルアミノスルホニ
ルー４−ニトロジフェニルエーテル（化合物番号１２の
化合物）の合成、２Ｗｔ％水酸化ナトリウム水溶液２．
５ｍ１に、７，４″−ジクロロー３−アミノスルホニル
ー４−ニトロジフェニルエーテル３．６ｇ（０．０１モ
ル）を溶解させた後、攪拌下、約２０℃にてクロロアセ
チルクロライド４．５ｇ（０．０４モル）と１０ｗｔ％
水酸化ナトリウム水溶液を交互に滴下し、ＰＨを１０〜
１１に調整した。After the dropwise addition was completed, the mixture was stirred three times, and then a dilute aqueous hydrochloric acid solution was added dropwise to adjust the LPH to 6.5, and the insoluble matter was removed. Next, the solution was acidified with strong hydrochloric acid, the precipitated crystals were collected, and after drying, they were re-crystallized from benzene to form pale yellow prismatic crystals with 2"
, 4″-dichloro-3-ethoxycarbonylaminosulfonyl-4-nitrodiphenyl ether (melting point 138~
140° C.) was obtained (2.5 g (yield 57%)). (2) 2″
, 4″-dichloro-3-chloroacetylaminosulfonyl-4-nitrodiphenyl ether (compound No. 12) synthesis, 2wt% sodium hydroxide aqueous solution2.
After dissolving 3.6 g (0.01 mol) of 7,4''-dichloro-3-aminosulfonyl-4-nitrodiphenyl ether in 5 ml of water, 4.5 g (0.01 mol) of chloroacetyl chloride was dissolved at about 20° C. under stirring. 04 mol) and 10 wt%
Add sodium hydroxide aqueous solution dropwise alternately to adjust the pH to 10~
Adjusted to 11.

滴下終了後、３紛間攪拌し、次いで水２００ｍ１を添加
して析出物を溶解させた後、希塩酸水溶液を滴下し、Ｐ
Ｈを４に調整し、不溶物を枦去した。次いで、枦液を強
塩酸酸性にし、析出した結晶を戸集し、乾燥後、ベンゼ
ンとｎ−ヘキサンの混合液から再結し、淡褐色プリズム
状結晶の２″，４−ジクロロー３−クロロアセチルアミ
ノスルホニルー４−ニトロジフェニルエーテル（融点１
４１〜１４３℃）を３．３ｇ（収率７５％）得た。（３
）２″，４″，６″一トリクロロー３−メトキシカルボ
ニルアミノスルホニルー４−ニトロジフェニルエーテル
のナトリウム塩（化合物番号２５の化合物）の合成、２
．５Ｗｔ％水酸化ナトリウム水溶液４０ｍ１に、２″，
４″，６″一トリクロロー３−アミノスルホニルー４−
ニトロジフェニルエーテル７．２ｇ（４）．０１８モル
）を溶解させた後、攪拌下、約２０℃にてクロロギ酸メ
チル７．５ｇ（イ）．０８モル）と１０ｗｔ％水酸化ナ
トリウム水溶液を交互に滴下し、ＰＨを１０−１１に調
整した。After the dropwise addition was completed, the powder was stirred, and then 200ml of water was added to dissolve the precipitate, and then a dilute hydrochloric acid aqueous solution was added dropwise.
H was adjusted to 4 and insoluble materials were removed. Next, the liquid solution was acidified with strong hydrochloric acid, the precipitated crystals were collected, dried, and re-crystallized from a mixture of benzene and n-hexane to form light brown prismatic crystals of 2'',4-dichloro-3-chloroacetyl. Aminosulfonyl-4-nitrodiphenyl ether (melting point 1
41-143°C) was obtained (3.3 g (yield 75%)). (3
) Synthesis of sodium salt of 2″,4″,6″-trichloro-3-methoxycarbonylaminosulfonyl-4-nitrodiphenyl ether (compound No. 25), 2
．． 2″ to 40ml of 5Wt% sodium hydroxide aqueous solution,
4″,6″-trichloro-3-aminosulfonyl-4-
Nitrodiphenyl ether 7.2g (4). After dissolving 7.5 g of methyl chloroformate (a) at about 20° C. while stirring. 08 mol) and a 10 wt% aqueous sodium hydroxide solution were added dropwise alternately to adjust the pH to 10-11.

滴下終了後、３紛間攪拌し、次いで析出物を沖集した後
、水洗、脱水、乾燥し、無色粉末状結晶の２″，４″，
６″一トリクロロー３−メトキシカルボニルアミノスル
ホニルー４−ニトロジフェニルエーテルのナトリウム塩
（１０５゜Ｃから次第に発泡分解）を６．６ｇ（収率７
７％）得た。（４）２″，４″，６″一トリクロロー３
−Ｎ，Ｎ−ジメチルアミノカルボニルアミノスルホニル
ー４ーニトロジフェニルエーテル（化合物番号２６の化
合物）の合成、アセトン８０ｍ１に、２″，４″，６″
一トリクロロー３−アミノスルホニルー４−ニトロジフ
ェニルエーテル？（イ）．００５モル）を溶解させた後
、炭カリウム１．１ｇ（０．００８モル）とＮ，Ｎ−ジ
メチルカルバモイルクロライド０．９ｇ（０．００８モ
ル）を添加し、帛時間煮沸還流した。After dropping, the powder was stirred for 3 minutes, and the precipitate was collected, washed with water, dehydrated, and dried to form colorless powdery crystals of 2″, 4″,
6.6 g (yield 7
7%) obtained. (4) 2″, 4″, 6″ one trichrome low 3
Synthesis of -N,N-dimethylaminocarbonylaminosulfonyl-4-nitrodiphenyl ether (compound number 26), 2″, 4″, 6″ in 80 ml of acetone
Mono-trichloro-3-aminosulfonyl-4-nitrodiphenyl ether? (stomach). After dissolving 1.1 g (0.008 mol) of potassium carbonate and 0.9 g (0.008 mol) of N,N-dimethylcarbamoyl chloride, the mixture was boiled and refluxed for a period of time.

次いで、アセ．トンンを留去した後、残留物を希水酸化
ナトリウム水溶液に溶解させ、希塩酸でＰＨを５．８に
調整し、不溶物をｐ去した。戸液を強塩酸酸性にし、析
出した結晶をｐ集し、乾燥後、ベンゼンとｎ−ヘキサン
の混合液から再結し、無色粉末２状結晶の２″，４″，
６″一トリクロロー３−Ｎ，Ｎ−ジメチルアミノカルボ
ニルアミノスルホニルー４−ニトロジフェニルエーテル
（融点１８６〜１９００Ｃ）を１ｇ（収率４３％）得た
。〕）２″，４″ージブロモー３−メトキシカルボニル
アミノスルホニルー４−ニトロジフェニルエーテル（化
合物番号３３の化合物）の合成、アセトン８０ｍｔに、
２″，４″ージブロモー３−アミノスルホニルー４−ニ
トロジフェニルエーテル２．３ｇ（イ）．００５モル）
を溶解させ、次いで炭酸カリウム１．１ｇ（０．００７
５モル）を添加し、さらに攪拌下、クロロギ酸メチル０
．７ｇ（０．００７５モル）を滴下した後、３時間加熱
還流した。Next, Ase. After distilling off the residue, the residue was dissolved in a dilute aqueous sodium hydroxide solution, the pH was adjusted to 5.8 with dilute hydrochloric acid, and the insoluble matter was removed. The solution was made acidic with strong hydrochloric acid, the precipitated crystals were collected, and after drying, they were re-crystallized from a mixture of benzene and n-hexane to form 2", 4", 2", 2", and 2" colorless powder crystals.
1 g (yield: 43%) of 6"-trichloro-3-N,N-dimethylaminocarbonylaminosulfonyl-4-nitrodiphenyl ether (melting point 186-1900C) was obtained.]) 2",4"-dibromo-3-methoxycarbonylamino Synthesis of sulfonyl-4-nitrodiphenyl ether (compound No. 33), in 80 mt of acetone,
2'',4''-dibromo 3-aminosulfonyl-4-nitrodiphenyl ether 2.3g (a). 005 mol)
and then 1.1 g (0.007
5 mol) was added, and while stirring, methyl chloroformate 0
．． After 7 g (0.0075 mol) was added dropwise, the mixture was heated under reflux for 3 hours.

次いで、冷却後、析出した無機塩を戸去し、戸液から溶
媒を留去した後、残留物を希水酸化ナトリウム水溶液に
溶解させた。次いで、不溶物を？去した後、希塩酸水溶
液を滴下しＰＨを６に調整し、析出した結晶を沖去した
。戸液を強塩酸酸性にし、析出した結晶を？集し、乾燥
後、ベンゼンとｎ−ヘキサンの混合液から再結し、淡黄
色針状結晶の′２′，４″ージブロモー３−メトキシカ
ルボニルアミノスルホニルー４−ニトロジフェニルエー
テル（融点１６７〜１７７Ｃ）を１．１ｇ（収率４４％
）得た。３）２″，４″−ジクロロー６″−フルオロー
３−メトキシカルボニルアミノスルホニルー４−ニトロ
ジフェニルエーテル（化合物番号３８の化合物）の合成
、２″，４″−ジクロロー６″−フルオロー３−アミノ
スルホニルー４−ニトロジフェニルエーテル２．０ｇ（
４）．００５モル）をアセトン８０ｍｔに溶解させた後
、炭酸カリウム１．２ｇ（０．００８モル）とクロロギ
酸メチル０．８ｇ（０．００８モル）を添加し、６時間
加熱還流した。After cooling, the precipitated inorganic salt was removed, and the solvent was distilled off from the solution, and the residue was dissolved in a dilute aqueous sodium hydroxide solution. Next, what about insoluble matter? After removing the solution, a dilute aqueous hydrochloric acid solution was added dropwise to adjust the pH to 6, and the precipitated crystals were removed. Make the solution acidic with strong hydrochloric acid and remove the precipitated crystals? After drying, it was re-crystallized from a mixture of benzene and n-hexane to give '2',4''-dibromo-3-methoxycarbonylaminosulfonyl-4-nitrodiphenyl ether (melting point 167-177C) in the form of pale yellow needle-like crystals. 1.1g (yield 44%
)Obtained. 3) Synthesis of 2″,4″-dichloro6″-fluoro3-methoxycarbonylaminosulfonyl-4-nitrodiphenyl ether (compound No. 38), 2″,4″-dichloro6″-fluoro3-aminosulfonyl- 2.0 g of 4-nitrodiphenyl ether (
4). 005 mol) in 80 mt of acetone, 1.2 g (0.008 mol) of potassium carbonate and 0.8 g (0.008 mol) of methyl chloroformate were added, and the mixture was heated under reflux for 6 hours.

次いで、冷却後、析出した無機塩をｐ去し、枦液から溶
媒を留去した後、残留物を希水酸化ナトリウム水溶液に
溶解させた。次いで、不溶物を？去した後、希塩酸水溶
液を滴下し、ＰＨを６に調整し、析出した結晶を戸去し
た。Next, after cooling, the precipitated inorganic salt was removed and the solvent was distilled off from the resin solution, and the residue was dissolved in a dilute aqueous sodium hydroxide solution. Next, what about insoluble matter? After removing the solution, a dilute aqueous hydrochloric acid solution was added dropwise to adjust the pH to 6, and the precipitated crystals were removed.

沖液を強塩酸酸性にし、析出した結晶を沖集し、乾燥後
、ベンゼンから再結し、淡黄色プリズム状結晶の２″，
４″−ジクロロー６゛−フルオロー３−メトキシカルボ
ニルアミノスルホニルー４−ニトロジフェニルエーテル
（融点１５２〜１５６℃）を１．３ｇ（収率５７％）得
た。この発明における、ジフェニルエーテル誘導体ィ、
除草剤として用いる場合には、農薬製剤の慣！１に従い
、不活性な固体担体、液体担体および乳化分散剤などを
用いて、粒剤、粉剤、乳剤、水和剤、錠剤、油剤、エア
ゾール、燻煙剤など任意の剤形にして使用することがで
きる。これらの不活性な担体としては例えば、タルク、
クレー、カオリン、ケイソウ土、炭酸カルシウム、塩素
酸カリウム、硝石、木粉、ニトロセルローズ、デンプン
、ベンゼン、キシレン、ｎ−ヘキサン、アラビアゴム、
塩化ビニール、炭酸ガス、フレオン、ブ０／マン、ブタ
ンなどを挙げることができる。また製剤上の補助剤、例
えば展着剤、希釈剤、界面活性剤、溶剤などを適宜配合
することができる。さらに、殺菌剤、殺虫剤およびその
他の農薬、尿素、硫安、リン安、カリ塩およびその他の
肥料物質、土壌改良剤などと適宜混合して使用すること
をできる。次に、この発明における除草剤の実施例を挙
げる。The liquid was made acidic with strong hydrochloric acid, the precipitated crystals were collected, dried, and re-crystallized from benzene to form pale yellow prismatic crystals of 2",
1.3 g (yield 57%) of 4''-dichloro6'-fluoro3-methoxycarbonylaminosulfonyl-4-nitrodiphenyl ether (melting point 152-156°C) was obtained.Diphenyl ether derivative in this invention,
When used as a herbicide, be sure to use pesticide formulations! According to 1.1, it can be used in any dosage form such as granules, powders, emulsions, wettable powders, tablets, oils, aerosols, smokes, etc. using inert solid carriers, liquid carriers, emulsifying dispersants, etc. I can do it. Examples of these inert carriers include talc,
Clay, kaolin, diatomaceous earth, calcium carbonate, potassium chlorate, saltpeter, wood flour, nitrocellulose, starch, benzene, xylene, n-hexane, gum arabic,
Examples include vinyl chloride, carbon dioxide, freon, butane, and butane. Further, auxiliary agents for formulation, such as spreading agents, diluents, surfactants, solvents, etc., may be appropriately added. Furthermore, it can be used by appropriately mixing with fungicides, insecticides, other agricultural chemicals, urea, ammonium sulfate, ammonium phosphorous, potassium salts and other fertilizer substances, soil conditioners, and the like. Next, examples of the herbicide according to the present invention will be given.

なお、各実施例中の部は重量部を意味する。実施例１２
″，３″−ジクロロー３−アミノスルホニルー４ーニト
ロジフェニルエーテル（化合物番号５の化合物）８部、
ベントナイト（９）部、タルク５娼、ネオペレックスパ
ウダー〔商品名：花王アトラス（株）製〕１部およびリ
グニンスルホン酸ソーダ２部とを均一に混合し、次いで
少量の水を添加し混練した後、造粒、乾燥して粒剤を得
た。In addition, parts in each example mean parts by weight. Example 12
8 parts of ″,3″-dichloro-3-aminosulfonyl-4-nitrodiphenyl ether (compound No. 5),
After uniformly mixing 9 parts of bentonite, 5 parts of talc, 1 part of Neoperex powder [trade name: manufactured by Kao Atlas Co., Ltd.] and 2 parts of sodium lignin sulfonate, then adding a small amount of water and kneading. , granulation, and drying to obtain granules.

実施例２ ２″，４″−ジクロロー３−メトキシカルボニルアミノ
スルホニルー４−ニトロジフェニルエーテル（化合物番
号９の化合物）５０５、カオリン４８部およびネオペレ
ックスパウダー２部とを均一に混合し、次いて粉砕して
水和剤を得た。Example 2 2″,4″-dichloro-3-methoxycarbonylaminosulfonyl-4-nitrodiphenyl ether (compound No. 9) 505, 48 parts of kaolin, and 2 parts of Neopelex powder were uniformly mixed and then ground. A hydrating agent was obtained.

実施例３ ２″，４″−ジクロロー３−エトキシカルボニルアミノ
スルホニルー４−ニトロジフェニルエーテル（化合物番
号１０の化合物）５娼、キシレン４娼、ジメチルホルム
アミド５部およびトキサノン〔商品名：三洋化成工業（
株）製〕５部とを均一に混合、溶解して乳剤を得た。Example 3 2″,4″-dichloro-3-ethoxycarbonylaminosulfonyl-4-nitrodiphenyl ether (compound No. 10) 5 parts, xylene 4 parts, dimethylformamide 5 parts, and toxanone [Product name: Sanyo Chemical Industries (
Co., Ltd.] were uniformly mixed and dissolved to obtain an emulsion.

実施例４ ２″，４″，６″一トリクロロー３−メトキシカルボニ
ルアミノスルホニルー４−ニトロジフェニルエーテル（
化合物番号２３の化合物）５部、タルク５０部およびカ
オリン４５部とを均一に混合し、粉剤を得た。Example 4 2″,4″,6″-trichloro-3-methoxycarbonylaminosulfonyl-4-nitrodiphenyl ether (
5 parts of Compound No. 23), 50 parts of talc, and 45 parts of kaolin were uniformly mixed to obtain a powder.

次に、実験例によつてこの発明における除草剤の効果を
、具体的に説明する。Next, the effects of the herbicide in this invention will be specifically explained using experimental examples.

なお、各実験例における供試化合物番号は、前述した化
合物番号と同一である。また、各実験例で施用した各薬
剤は、いずれも実施例２に準じて製剤した水和剤を、有
効成分の濃度が１０００ｐｐｍになるように水で希釈し
たものである。実験例１水田土壌処理実験 −アールのワグネルポツトに、宇部土壌（沖積壌土）を
充填し、タイヌビエの種子、ミズガヤツリとウリカワの
塊茎およびマツバイの株を植え、軽く覆土した後、上層
にコナギとホタルイの種子を播き、さらに２葉期の水稲
苗（品種：日本晴）を移植し、水を加えて水深３ｃｍの
湛水状態とした。In addition, the test compound number in each experimental example is the same as the compound number mentioned above. In addition, each drug applied in each experimental example was a wettable powder prepared according to Example 2 and diluted with water so that the concentration of the active ingredient was 1000 ppm. Experimental Example 1 Paddy soil treatment experiment - Earl's Wagner pot was filled with Ube soil (alluvial loam), planted with seeds of Japanese cabbage, tubers of Japanese cypress, tubers of Japanese cypress, and stocks of Japanese pine tree. Seeds were sown, and paddy rice seedlings (variety: Nipponbare) at the two-leaf stage were transplanted, and water was added to create a flooded state at a depth of 3 cm.

次いで雑草発芽時に、各薬剤をピペットで所定量均一に
滴下処理し、平均気温２５℃のガラス室て管理した。薬
剤処理後３週間目に各供試化合物の除草効果を調査した
。その結果を第２表に示）す。なお、第２表中の除草効
果は下記の基準によつた。Then, when the weeds germinated, a predetermined amount of each drug was uniformly dropped using a pipette, and the weeds were kept in a glass room at an average temperature of 25°C. Three weeks after the chemical treatment, the herbicidal effects of each test compound were investigated. The results are shown in Table 2). The herbicidal effects in Table 2 were based on the following criteria.

５：完全枯死４：大害３：中害２：小害 １：僅小害０：無害（正常発育） 実施例２多年生雑草生育期別処理実験 ±アールのワグネルポツトに、宇部土壌を充５０００−
ゝ填し、ミズガヤツリとウリカワの塊茎を植え、水を加
えて水深３Ｃ７！の湛水状態とした。5: Complete withering 4: Major damage 3: Medium damage 2: Slight damage 1: Slight damage 0: No harm (normal growth) Example 2 Perennial weed growth period treatment experiment ± Earl's Wagner pot was filled with Ube soil 5000-
Fill it up, plant tubers of Mizugaya vine and Urikawa, and add water to a water depth of 3C7! It was assumed to be in a flooded state.

ミズガヤツリの発芽前、および５Ｃ７１の草丈、１０ｃ
ｍの草丈になつた時、またウリカワの発芽前、および２
葉期，４葉期になつた時、各薬剤をピペットで所定量均
一に滴下処理し、平均気温２５℃のガラス室で管理・し
た。薬剤処理後、２週間目に各供試化合物の除草効果を
調査した。その結果を、第３表に示す。なお、第３表中
の除草効果の基準は、実験例１と同一である。実験例３
畑地土壌処理実験 ーアールのワグネルポツトに宇部土壌を充填しコムギ（
品種：コブシコムギ）、大豆（品種：夏大豆１号）、メ
ヒシバ、イヌビエ、スベリヒユ、ツメクサ、タネツケバ
ナの種子を播種し、覆土後、各薬剤を土壌表層に所定量
均一に加圧噴霧処理し、平均気温２５℃のガラス室で管
理した。Plant height of 5C71 before germination and 5C71, 10c
When the plant reaches a height of m, and before the germination of urikawa, and
When the leaves reached the leaf stage and the four-leaf stage, a predetermined amount of each drug was uniformly dropped using a pipette, and the plants were kept in a glass room with an average temperature of 25°C. Two weeks after the chemical treatment, the herbicidal effects of each test compound were investigated. The results are shown in Table 3. Note that the criteria for the herbicidal effect in Table 3 are the same as in Experimental Example 1. Experimental example 3
Upland soil treatment experiment - Earl's Wagner pot was filled with Ube soil and wheat (
Seeds of soybean (variety: Kobushi wheat), soybean (variety: Summer soybean No. 1), blackberry grass, goldenrod, purslane, Japanese clover, and ash seedlings were sown, and after covering the soil, a predetermined amount of each chemical was sprayed uniformly under pressure on the soil surface, and the average It was maintained in a glass room at a temperature of 25°C.

薬剤処理後、２週間目に各供試化合物の除草効果を調査
した。その結果を第４表に示す。なお、第４表中の除草
効果の基準は、実験例１と同一である。Two weeks after the chemical treatment, the herbicidal effects of each test compound were investigated. The results are shown in Table 4. Note that the criteria for the herbicidal effect in Table 4 are the same as in Experimental Example 1.

実験例４畑地茎葉処理実験 彌アールのワグネルポツトに宇部土壌を充填し、３葉期
のメヒシバ、２葉期のオナモミ、２葉期のシロザおよび
３葉期のハマスゲを育成した。Experimental Example 4 Field Stem and Leaves Treatment Experiment A Wagner pot in Yaar was filled with Ube soil, and three-leafed crabgrass, two-leafed Japanese fir, two-leafed white locust, and three-leafed Japanese commonweed were grown.

次いで、各供試化合物の水和剤を展着剤ネオエステリン
〔商品名：東亜農薬（株）製〕１００ｐｐｍを含む゛水
で希釈した薬剤（有効成分濃度１０００ｐｐｍ）を、１
ポット当り５ｍｔづつ茎葉に均一に加圧噴霧処理し、平
均気温２５℃のガラス室で管理した。薬剤処理後、２週
間目に各供試化合物の除草効果を調査した。その結果を
、第５表に示す。なお、第５表中の除草効果の基準は、
実験例１と同一である。Next, a drug (active ingredient concentration 1000 ppm) prepared by diluting the hydrating agent of each test compound with water containing 100 ppm of the spreading agent Neoesterin [trade name: manufactured by Toa Nohyaku Co., Ltd.] was added to
The leaves and stems were uniformly pressure sprayed at a rate of 5 mt per pot, and maintained in a glass room with an average temperature of 25°C. Two weeks after the chemical treatment, the herbicidal effects of each test compound were investigated. The results are shown in Table 5. In addition, the criteria for herbicidal effectiveness in Table 5 are as follows:
Same as Experimental Example 1.

以上の各実験結果から、この発明の除草剤は土壌処理あ
るいは茎葉処理を施すことにより、作物に全く薬害を与
えることなく、広範な諸雑草を効果的に防除できること
が解り、この発明の除草剤は極めて優れた除草剤である
ことが認識される。From the above experimental results, it was found that the herbicide of this invention can effectively control a wide range of weeds without causing any chemical damage to crops by applying soil treatment or foliage treatment. is recognized as an extremely effective herbicide.

Claims (1)

【特許請求の範囲】 １ 一般式 ▲数式、化学式、表等があります▼ （ただし、式中Ｘはハロゲン原子を示し、ｎは１〜３の
整数を示し、Ｒは水素原子、低級アルコキシカルボニル
基、アセチル基、クロルアセチル基、Ｎ、Ｎ−ジメチル
カルバモイル基を示す。 ）で表わされるジフェニルエーテル誘導体。２ 一般式 ▲数式、化学式、表等があります▼ （ただし、式中Ｘはハロゲン原子を示し、ｎは１〜３の
整数を示し、Ｒは水素原子、低級アルコキシカルボニル
基、アセチル基、クロルアセチル基、Ｎ、Ｎ−ジメチル
カルバモイル基を示す。 ）で表わされるジフェニルエーテル誘導体を有効成分と
して含有することを特徴とする除草剤[Claims] 1. General formula▲ Numerical formula, chemical formula, table, etc.▼ (However, in the formula, , acetyl group, chloroacetyl group, N,N-dimethylcarbamoyl group). 2 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (However, in the formula, X represents a halogen atom, n represents an integer from 1 to 3, and R represents a hydrogen atom, lower alkoxycarbonyl group, acetyl group, chloroacetyl A herbicide characterized by containing a diphenyl ether derivative represented by (N,N-dimethylcarbamoyl group) as an active ingredient.
JP52089729A 1977-07-28 1977-07-28 Diphenyl ether derivatives and herbicides containing diphenyl ether derivatives Expired JPS6054954B2 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
JP52089729A JPS6054954B2 (en) 1977-07-28 1977-07-28 Diphenyl ether derivatives and herbicides containing diphenyl ether derivatives
GB787830523A GB2001635B (en) 1977-07-28 1978-07-20 Diphenyl ether derivatives process for preparing the same and herbicidal compositions containing the same
DE19782833021 DE2833021A1 (en) 1977-07-28 1978-07-27 DIPHENYLA ETHER DERIVATIVES, PROCESS FOR THEIR PRODUCTION AND HERBICIDE AGENTS CONTAINING THEM
NL7807967A NL7807967A (en) 1977-07-28 1978-07-27 NEW DIPHENYL ETHER DERIVATIVES, METHOD FOR PREPARING THEM, AND HERBICIDE PREPARATIONS CONTAINING SUCH A COMPOUND.
IT26201/78A IT1097782B (en) 1977-07-28 1978-07-27 DIPHENYL ETHER DERIVATIVES, PROCEDURE TO PREPARE THE SAME AND HERBICIDE COMPOSITIONS CONTAINING THE SAME
BR7804864A BR7804864A (en) 1977-07-28 1978-07-27 DIFENYLETER DERIVATIVES, PROCESS FOR THEIR PREPARATION AND HERBICIDAL COMPOSITIONS CONTAINING THE SAME
SU782646951A SU843695A3 (en) 1977-07-28 1978-07-27 Herbicidic composition
CA308,293A CA1111062A (en) 1977-07-28 1978-07-27 Diphenyl ether derivatives, process for preparing the same and herbicidal compositions containing the same
FR7822495A FR2398728A1 (en) 1977-07-28 1978-07-28 DIPHENYL ETHER DERIVATIVES AND THEIR MANUFACTURING PROCESS AS WELL AS HERBICIDAL COMPOSITIONS CONTAINING THESE DERIVATIVES
US06/006,919 US4213775A (en) 1977-07-28 1979-01-26 Diphenyl ether derivatives and herbicidal compositions containing the same
PH22142A PH15699A (en) 1977-07-28 1979-01-30 Diphenyl ether derivatives,process for preparing the same and herbicidal composition containing the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP52089729A JPS6054954B2 (en) 1977-07-28 1977-07-28 Diphenyl ether derivatives and herbicides containing diphenyl ether derivatives

Publications (2)

Publication Number Publication Date
JPS5424851A JPS5424851A (en) 1979-02-24
JPS6054954B2 true JPS6054954B2 (en) 1985-12-03

Family

ID=13978837

Family Applications (1)

Application Number Title Priority Date Filing Date
JP52089729A Expired JPS6054954B2 (en) 1977-07-28 1977-07-28 Diphenyl ether derivatives and herbicides containing diphenyl ether derivatives

Country Status (9)

Country Link
JP (1) JPS6054954B2 (en)
BR (1) BR7804864A (en)
CA (1) CA1111062A (en)
DE (1) DE2833021A1 (en)
FR (1) FR2398728A1 (en)
GB (1) GB2001635B (en)
IT (1) IT1097782B (en)
NL (1) NL7807967A (en)
SU (1) SU843695A3 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3114072A1 (en) * 1981-04-08 1982-11-04 Basf Ag, 6700 Ludwigshafen HERBICIDES DIPHENYL ETHER, THE PRODUCTION AND USE THEREOF AS HERBICIDES
US4959501A (en) * 1987-09-04 1990-09-25 Ciba-Geigy Corporation Process for the preparation of 2-(2-chloroethoxy)-benzenesulfonamide
DE4015834A1 (en) * 1990-05-17 1991-11-21 Bayer Ag New phenoxy:phenyl-sulphonyl cpds. - used as defoliant(s), desiccant(s) and weed-killer(s)
DE4023040A1 (en) * 1990-07-20 1992-01-23 Bayer Ag HERBICIDES BASED ON SULFONYLATED (THIO) CARBAMID ACID ESTERS, NEW SULFONYLATED CARBAMID ACID ESTERS AND METHOD FOR THE PRODUCTION THEREOF

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3776961A (en) * 1971-12-23 1973-12-04 Oil Corp 3-substituted 4-nitrophenyl halophenyl ethers

Also Published As

Publication number Publication date
FR2398728A1 (en) 1979-02-23
FR2398728B1 (en) 1982-05-28
IT7826201A0 (en) 1978-07-27
SU843695A3 (en) 1981-06-30
NL7807967A (en) 1979-01-30
GB2001635B (en) 1982-01-27
GB2001635A (en) 1979-02-07
BR7804864A (en) 1979-04-24
DE2833021A1 (en) 1979-02-08
JPS5424851A (en) 1979-02-24
IT1097782B (en) 1985-08-31
CA1111062A (en) 1981-10-20

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