JPS5934705B2 - Phenoxyphenoxyalkane nitrile derivatives and herbicides containing them - Google Patents
Phenoxyphenoxyalkane nitrile derivatives and herbicides containing themInfo
- Publication number
- JPS5934705B2 JPS5934705B2 JP2308476A JP2308476A JPS5934705B2 JP S5934705 B2 JPS5934705 B2 JP S5934705B2 JP 2308476 A JP2308476 A JP 2308476A JP 2308476 A JP2308476 A JP 2308476A JP S5934705 B2 JPS5934705 B2 JP S5934705B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- phenoxyphenoxyalkane
- general formula
- hydrogen atom
- 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
Links
- 150000002825 nitriles Chemical class 0.000 title claims description 9
- 239000004009 herbicide Substances 0.000 title claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- -1 Phenoxyphenoxy Chemical group 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 229910052801 chlorine Chemical group 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 230000002363 herbicidal effect Effects 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000002689 soil Substances 0.000 description 16
- 241000196324 Embryophyta Species 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
- 241000192043 Echinochloa Species 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- AOMOITJLVAKCBG-UHFFFAOYSA-N 2-[2-bromo-5-[2-chloro-4-(trifluoromethyl)phenoxy]phenoxy]butanenitrile Chemical compound C1=C(Br)C(OC(CC)C#N)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 AOMOITJLVAKCBG-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 244000088415 Raphanus sativus Species 0.000 description 2
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- 239000002420 orchard Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- FNMKGECWMNKRJE-UHFFFAOYSA-N 2-(1-cyanoethoxy)-4-[2,6-dichloro-4-(trifluoromethyl)phenoxy]benzonitrile Chemical compound C1=C(C#N)C(OC(C)C#N)=CC(OC=2C(=CC(=CC=2Cl)C(F)(F)F)Cl)=C1 FNMKGECWMNKRJE-UHFFFAOYSA-N 0.000 description 1
- XMWMJIWGHLMYIC-UHFFFAOYSA-N 2-[2-bromo-5-[2,6-dichloro-4-(trifluoromethyl)phenoxy]phenoxy]propanenitrile Chemical compound C1=C(Br)C(OC(C)C#N)=CC(OC=2C(=CC(=CC=2Cl)C(F)(F)F)Cl)=C1 XMWMJIWGHLMYIC-UHFFFAOYSA-N 0.000 description 1
- QNEIDVNZWHPSFJ-UHFFFAOYSA-N 2-[2-bromo-5-[2-chloro-4-(trifluoromethyl)phenoxy]phenoxy]propanenitrile Chemical compound C1=C(Br)C(OC(C)C#N)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 QNEIDVNZWHPSFJ-UHFFFAOYSA-N 0.000 description 1
- RRFKGGBRJCSKIT-UHFFFAOYSA-N 2-[2-chloro-5-[2-chloro-4-(trifluoromethyl)phenoxy]phenoxy]propanenitrile Chemical compound C1=C(Cl)C(OC(C)C#N)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 RRFKGGBRJCSKIT-UHFFFAOYSA-N 0.000 description 1
- ZWAUTKVWPOCJJH-UHFFFAOYSA-N 2-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-iodophenoxy]butanenitrile Chemical compound C1=C(I)C(OC(CC)C#N)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 ZWAUTKVWPOCJJH-UHFFFAOYSA-N 0.000 description 1
- WYGZIYJWWOOMJJ-UHFFFAOYSA-N 2-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenoxy]propanenitrile Chemical compound C1=C([N+]([O-])=O)C(OC(C)C#N)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 WYGZIYJWWOOMJJ-UHFFFAOYSA-N 0.000 description 1
- AXMLVXFKDZQAPX-UHFFFAOYSA-N 4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-(1-cyanopropoxy)benzonitrile Chemical compound C1=C(C#N)C(OC(CC)C#N)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 AXMLVXFKDZQAPX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- QHDRKFYEGYYIIK-UHFFFAOYSA-N isovaleronitrile Chemical compound CC(C)CC#N QHDRKFYEGYYIIK-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
【発明の詳細な説明】
本発明は新規なフエノキシフエノキシアルカンニトリル
誘導体およびそれらを含有する除草剤に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel phenoxyphenoxyalkane nitrile derivatives and herbicides containing them.
さら（こ詳しくは、
本発明は、一般式
（式中Ｘは水素原子または塩素原子であり、Ｙはニトロ
基、シアノ基またはハロゲン原子であり、Ｒは水素原子
または低級アルキル基である）で表わされるフエノキシ
フエノキシアルカンニトリル誘導体およびそれらの少く
とも一種を有効成分として含有することを特徴とする除
草剤である。(More specifically, the present invention is based on the general formula (wherein, X is a hydrogen atom or a chlorine atom, Y is a nitro group, a cyano group, or a halogen atom, and R is a hydrogen atom or a lower alkyl group) This herbicide is characterized by containing the following phenoxyphenoxyalkane nitrile derivatives and at least one thereof as an active ingredient.
前記一般式中、Ｙで表わされるハロゲン原子としては塩
素原子、臭素原子、弗素原子などが挙げらＲで表わされ
る低級アルキル基としてはメチル基、エチル基、ｎ−プ
ロピル基、ＪｓＯ−ｐプロピル基、ｎ−ブチル基などが
挙げられる。なお前記一般式で表わされるフエノキシフ
エノキシアルカンニトリル誘導体のうち、Ｙがニトロ基
或はシアノ基である化合物群で、かつＲがメチル基また
はエチル基であるものは、除草効果面からみて或は合成
面での経済性からみて特に望ましい化合物群といえる。In the above general formula, examples of the halogen atom represented by Y include a chlorine atom, a bromine atom, a fluorine atom, etc., and examples of the lower alkyl group represented by R include a methyl group, an ethyl group, an n-propyl group, and a JsO-p propyl group. , n-butyl group, etc. Among the phenoxyphenoxyalkane nitrile derivatives represented by the above general formula, those in which Y is a nitro group or a cyano group, and R is a methyl group or an ethyl group, have a herbicidal effect. Alternatively, they can be said to be a particularly desirable group of compounds from the economical point of view of synthesis.
本発明のフエノキシフエノキシアルカンニトリル誘導体
は通常例えば下記方式のいずれかにより製浩される。The phenoxyphenoxyalkane nitrile derivative of the present invention is usually produced, for example, by any of the following methods.
上記各反応式中、Ｘは水素原子または塩素原子を、Ｙは
ニトロ基、シアノ基またはハロゲン原子を、Ｒは水素原
子または低級アルキル基を、ＨａｌＯはハロゲン原子を
示す。In each of the above reaction formulas, X represents a hydrogen atom or a chlorine atom, Y represents a nitro group, a cyano group, or a halogen atom, R represents a hydrogen atom or a lower alkyl group, and HalO represents a halogen atom.
製造例 １
α−〔２−ニトロ−５−（２−クロロ−４−トリフルオ
ロメチルフエノキシ）フエノキシ〕プロピオニトリル２
−クロロ−４−トリフルオロメチル−３′−ヒドロキシ
−４′−ニトロジフエニルエーテル６．５ｇをメチルエ
チルケトン１０ｍ１，に溶解させ、さらにこれにα−プ
ロモプロピオニトリル４９および無水炭酸カリウム５ｇ
を加えて、攪拌下に８０℃で５時間反応させた。Production example 1 α-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionitrile 2
-Dissolve 6.5 g of chloro-4-trifluoromethyl-3'-hydroxy-4'-nitrodiphenyl ether in 10 ml of methyl ethyl ketone, and add 49 g of α-promopropionitrile and 5 g of anhydrous potassium carbonate.
was added, and the mixture was reacted at 80° C. for 5 hours with stirring.
反応物を適量の水中に投入し、クロロホルムで抽出後、
抽出相を洗浄、乾喋した。さらにクロロホルムを留去後
、減圧蒸留してＢｐｌ９Ｏ〜１９３ルＣ／１ｗ１ｔＨ９
の目的物５９を得た。製造例 ２
α−〔２−シアノ−５−（２−クロロ−４−トリフルオ
イメチルフエノキシ）フエノキシ〕ブチロニトリルα−
〔２−ブロモ−５−（２−クロロ−４−トリフルオロメ
チルフエノキシ）フエノキシ〕ブチロニトリル１０９を
ジメチルホルムアミド２０ｍ１に溶解させ、さらにこれ
にシアン化第一銅２．５９を加えて、撹拌下ｌこ１４５
〜１５０℃で２時間反応させた。The reaction product was poured into an appropriate amount of water, extracted with chloroform,
The extract phase was washed and blotted dry. Furthermore, after distilling off chloroform, Bpl9O~193LC/1w1tH9 was distilled under reduced pressure.
Target product 59 was obtained. Production Example 2 α-[2-cyano-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]butyronitrile α-
[2-bromo-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]butyronitrile 109 was dissolved in 20 ml of dimethylformamide, and 2.59 cuprous cyanide was added thereto, and the mixture was stirred. lko145
The reaction was carried out at ~150°C for 2 hours.
反応物を放冷後、適量の塩化第二鉄水溶液中に投入し、
クロロホルムで抽出した。抽出相を水洗、乾燥し、さら
にクロロホルムを留去した後、減圧蒸留してＢｐ．２Ｏ
２〜２０７℃／２Ｗ１田の目的物７９を得た。なお下記
する化合物ｌこついても、上記製造方法或は製造例に準
じて製造さへ後記植物試験によつて除草効果が確認され
た。After cooling the reaction product, it was poured into an appropriate amount of ferric chloride aqueous solution,
Extracted with chloroform. The extracted phase was washed with water, dried, and chloroform was distilled off, followed by distillation under reduced pressure to obtain Bp. 2O
Target product 79 was obtained at 2-207°C/2W1. The herbicidal effect of the following compound was confirmed by the plant test described below, which was produced according to the above-mentioned production method or production example.
α−〔２−ニトロ−５−（２−クロロ−４−トリフルオ
ロメチルフエノキシ）フエノキシ〕ブチロニトリル（Ｂ
ｐｌ９５〜２０『Ｃ／１．５７１１１１Ｈｇ）α−〔２
−ニトロ−５−（２−クロロ−４−トリフルオロメチル
フエノキシ）フエノキシ〕バレロニトリル（Ｂｐ２Ｏｌ
〜２０５℃／１１１ＩＩ１Ｈ９）α−〔２−ニトロ−５
−（２−クロロ−４−トリフルオロメチルフエノキシ）
フエノキシ〕アセトニトリル（Ｂｐｌ９ｌ〜１９３℃／
２？丁？）α−〔２−ニトロ−５−（２，６−ジクロロ
−４−トリフルオロメチルフエノキシ）フエノキシ〕ブ
チロニトリル（Ｂｐ２ｌＯ〜２１３℃／１．５？…０α
−〔２−シアノ−５−（２−クロロ−４−トリフルオロ
メチルフエノキシ）フエノキシ〕プロピオニトリル（Ｍ
ｐｌ４４〜１４６℃）α一〔２−シアノ−５−（２−ク
ロロ−４−トリフルオロメチルフエノキシ）フエノキシ
〕ＩｓＯ−バレロニトリル（Ｂｐｌ９９〜２０３シＣ／
１７１１１１ｔ眠）α−〔２−シアノ−５−（２−クロ
ロ−４−トリフルオロメチルフエノキシ）フエノキシ］
アセトニトリルα−〔２−シアノ−５−（２，６−ジク
ロロ−４−トリフルオロメチルフエノキシ）フエノキシ
〕プロピオニトリル（Ｂｐ２Ｏ７〜２１１℃／１．５？
Ｈｇ）α−〔２−ブロモ−５−（２−クロロ−４−トリ
フルオロメチルフエノキシ）フエノキシ〕プロピオニト
リル（Ｂｐｌ９Ｏ〜１９２℃／２．５顧Ｈ９）α−〔２
−ブロモ−５−（２−クロロ−４−トリフルオロメチル
フエノキシ）フエノキシ〕ブチロニトリル（Ｂｐｌ９５
〜２００℃／２．５７１ｉ！１Ｈ９）α−〔２−ブロモ
−５−（２−クロロ−４−トリフルオロメチルフエノキ
シ）フエノキシ〕アセトニトリル（ＭｐｌｌＯ〜１１２
゜ｃ）α−〔２−ブロモ−５−（２，６−ジクロロ−４
−トリフルオロメチルフエノキシ）フエノキシ〕プロピ
オニトリルα−〔２−クロロ−５−（２−クロロ−４−
トリフルオロメチルフエノキシ）フエノキシ〕プロピオ
ニトリル（Ｂｐｌ８３〜１８８℃／２ＨＩ１Ｈ９）α−
〔２−ヨード−５−（２−クロロ−４−トリフルオロメ
チルフエノキシ）フエノキシ〕ブチロニトリル（Ｂｐｌ
９５〜２０２゜Ｃ／２？Ｈ９）本発明のフエノキシフエ
ノキシアルカンニトリル誘導体は、後記試験例にみる通
り、除草剤の有効成分として使用した場合に、各種雑草
に対してすぐれた除草効果をもたらす。α-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]butyronitrile (B
pl95~20 "C/1.571111Hg) α-[2
-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]valeronitrile (Bp2Ol
~205℃/111II1H9)α-[2-nitro-5
-(2-chloro-4-trifluoromethylphenoxy)
phenoxy]acetonitrile (Bpl9l~193℃/
2? Ding? )α-[2-nitro-5-(2,6-dichloro-4-trifluoromethylphenoxy)phenoxy]butyronitrile (Bp2lO~213°C/1.5?...0α
-[2-cyano-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionitrile (M
pl44-146℃) α-[2-cyano-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]IsO-valeronitrile (Bpl99-203C/
171111t)α-[2-cyano-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]
Acetonitrile α-[2-cyano-5-(2,6-dichloro-4-trifluoromethylphenoxy)phenoxy]propionitrile (Bp2O7~211°C/1.5?
Hg) α-[2-Bromo-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionitrile (Bpl9O~192℃/2.5℃H9)α-[2
-Bromo-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]butyronitrile (Bpl95
~200℃/2.571i! 1H9) α-[2-bromo-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]acetonitrile (MpllO~112
°c) α-[2-bromo-5-(2,6-dichloro-4
-trifluoromethylphenoxy)phenoxy]propionitrile α-[2-chloro-5-(2-chloro-4-
Trifluoromethylphenoxy)phenoxy]propionitrile (Bpl83-188℃/2HI1H9) α-
[2-iodo-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]butyronitrile (Bpl
95~202°C/2? H9) As shown in the test examples below, the phenoxyphenoxyalkane nitrile derivatives of the present invention exhibit excellent herbicidal effects on various weeds when used as an active ingredient of herbicides.
とりわけ水稲田での使用において、水稲に対する薬害を
最少限にとどめうること或は土壌処理において優れた活
性を呈することは注目される。その除橢１としての適用
範囲は水田をはじめ、畑地、果樹園、桑園、山林、農道
、グラウンド、工場敷地など多岐にわたり、適用方法も
土壌処理以外に茎葉処理も適宜選択できる。実施に際し
ては、各適用方法に応じて水に分散して使用したり、希
釈剤、溶剤、乳化剤、展着剤などの各種補助剤を配合し
て乳剤、液剤、水和剤、粉剤、粒剤などの形態に製剤し
て使用できる。さらには他の除草斉り、殺虫剤、殺菌剤
などの農薬類、或は肥料、土壌などと混用、併用するこ
とができ、この場合に一層すぐれた効果を示す場合もあ
る。本発明に係る除草斉りの施用適量は気象条件、土壌
条件、薬剤の製剤形態、施用時期、施用方法、対象雑草
の種類などの相違により一概に規定できないが、一般に
１アール当りの施用有効成分量として１〜５００９望ま
しくは５〜１００９である。In particular, when used in paddy rice fields, it is noteworthy that phytotoxicity to paddy rice can be minimized and that it exhibits excellent activity in soil treatment. The scope of its application as dirt removal 1 is wide-ranging, including paddy fields, fields, orchards, mulberry orchards, mountain forests, farm roads, grounds, and factory grounds, and the method of application can be appropriately selected from soil treatment as well as foliage treatment. Depending on the application method, it may be dispersed in water or mixed with various auxiliary agents such as diluents, solvents, emulsifiers, and spreading agents to form emulsions, solutions, wettable powders, powders, and granules. It can be formulated and used in the following forms. Furthermore, it can be mixed or used in combination with other weed killers, agricultural chemicals such as insecticides and fungicides, fertilizers, soil, etc. In this case, even better effects may be exhibited. The appropriate amount to be applied for simultaneous weeding according to the present invention cannot be determined unconditionally due to differences in weather conditions, soil conditions, drug formulation, application timing, application method, type of target weed, etc., but in general, the amount of active ingredient to be applied per are. The amount is 1 to 5009, preferably 5 to 1009.
以下に本発明に係る除草剤の植物試験及び製剤の実施例
を記載するが、勿論本発明はこれらの記載のみに限定さ
れるものではない。試験例 １
１／１０，０００アールポツトに土壌を入れ、水を過飽
和状態に含浸させ、風乾したヒエ種子の一定量を播種し
、その上を軽く覆土し八 ヒエが地上面に発芽したとき
にポツトを水深３ｃ１ｎの湛水状態とし、次いで各有効
成分の水分散液を濯注処理した。Examples of plant tests and formulations of herbicides according to the present invention will be described below, but the present invention is not limited to these descriptions. Test Example 1 Put soil in a 1/10,000 are pot, soak it with water to a supersaturated state, sow a certain amount of air-dried barnyard grass seeds, and lightly cover the soil with soil. was submerged in water to a depth of 3 cm, and then rinsed with an aqueous dispersion of each active ingredient.
処理後１４日目にポツト中の生存ヒエを抜取り、その後
これを風乾し重量を測定した。生存雑草量の無処理区に
対する百分率を算出しこれを生育度として第１表の結果
を得た。試験例 ２
１／１０，０００アールポツトに土壌を入れ、水を過飽
和状態に含浸させ、その上に一定量の雑草種子を含有す
る土壌を軽く覆土した。On the 14th day after the treatment, the surviving barnyard grasses were removed from the pots, and then air-dried and their weights were measured. The percentage of the amount of surviving weeds relative to the untreated area was calculated, and this was used as the growth degree to obtain the results shown in Table 1. Test Example 2 Soil was placed in a 1/10,000 are pot, impregnated with water to a supersaturated state, and the soil was lightly covered with soil containing a certain amount of weed seeds.
その後湛水して水深を３？に保持し、７日目、各雑草の
発生が揃つたときに有効成分水分散液を所定量散布した
。薬液処理後１４日目に雑草の生育状態を観察し、第２
表の結果を得た。表中の数値５は完全に生育を抑制した
ことを示し、以下５段階に分けて生育抑制程度を表わし
た。試験例 ３
１／３，０００アールバツトに土壌を入れ、畑状態とし
て一定量のヒエおよび大根種子を播種し、その上にメヒ
シバ、ケイヌビエ、エノコログサ、ノミノフスマ、タネ
ツケバナ、アカザ、オオイヌタデ、アゼガヤツリ、ノボ
ロギクなどの一般雑草の種子を含有する土壌を約１（１
−JモV！の厚さに覆土した。After that, it was flooded and the water depth was 3? On the 7th day, when all weeds had appeared, a predetermined amount of an aqueous dispersion of the active ingredient was sprayed. The growth condition of the weeds was observed on the 14th day after the chemical solution treatment, and the second
Obtained the results in the table. A value of 5 in the table indicates that growth was completely inhibited, and the degree of growth inhibition was divided into five levels below. Test Example 3 Soil is placed in a 1/3,000-area pot, and a certain amount of barnyard grass and radish seeds are sown in a field condition. Approximately 1 (1
-JMoV! It was covered with soil to a thickness of .
播種３日目に有効成分水分散液（有効成分量１００９／
ａ）を土壌面に散布した。薬液処理後２０日目に雑草の
生育状態を観察し、第３表の結果を得た。表の数値１０
は完全に生育を抑制したことを示し、以下１０段階に分
けて生育抑制程度を表わした。試験例 ４
１／１０，０００アールポツトに土壌を入れて畑状態と
し、そこにヒエ、大根および大豆種子の一定量を播種し
、約１ｃＴｎの厚さに覆土した。On the 3rd day of sowing, apply the active ingredient aqueous dispersion (active ingredient amount 1009/
a) was sprayed on the soil surface. The growth state of the weeds was observed on the 20th day after the chemical solution treatment, and the results shown in Table 3 were obtained. Number 10 in the table
indicates that growth was completely inhibited, and the degree of growth inhibition was divided into 10 stages below. Test Example 4 Soil was placed in a 1/10,000 are pot to prepare a field, and a certain amount of barnyard grass, radish, and soybean seeds were sown there, and the soil was covered with soil to a thickness of about 1 cTn.
Claims (1)
基、シアノ基またはハロゲン原子であり、Ｒは水素業子
または低級アルキル基である）で表わされるフェノキシ
フェノキシアルカンニトリル誘導体の少くとも一種を有
効成分として含有することを特徴とする除草剤。 ２ 有効成分が一般式 ▲数式、化学式、表等があります▼ （式中Ｘは水素原子または塩素原子であり、Ｒはメチル
基またはエチル基である）で表わされるフェノキシフェ
ノキシアルカンニトリル誘導体である特許請求の範囲第
１項記載の除草剤。 ３ 有効成分が一般式 ▲数式、化学式、表等があります▼ （式中Ｘは水素原子または塩素原子であり、Ｒはメチル
基またはエチル基である）で表わされるフェノキシフェ
ノキシアルカンニトリル誘導体である特許請求の範囲第
１項記載の除草剤。 ４ 一般式 ▲数式、化学式、表等があります▼ （式中Ｘは水素原子または塩素原子であり、Ｙはニトロ
基、シアノ基またはハロゲン原子であり、Ｒは水素原子
または低級アリキル基である）で表わされるフェノキシ
フェノキシアルカンニトリル誘導体。 ５ 一般式 ▲数式、化学式、表等があります▼ （式中Ｘは水素原子または塩素原子であり、Ｒはメチル
基またはエチル基である）で表わされる特許請求の範囲
第４項記載のフェノキシフェノキシアルカンニトリル誘
導体。 ６ 一般式 ▲数式、化学式、表等があります▼ （式中Ｘは水素原子または塩素原子であり、Ｒはメチル
基またはエチル基である）で表わされる特許請求の範囲
第４項記載のフェノキシフェノキシアルカンニトリル誘
導体。[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, or a lower alkyl group) as an active ingredient. 2. A patent in which the active ingredient is a phenoxyphenoxyalkane nitrile derivative represented by the general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (wherein X is a hydrogen atom or a chlorine atom, and R is a methyl group or an ethyl group) The herbicide according to claim 1. 3. A patent in which the active ingredient is a phenoxyphenoxyalkane nitrile derivative represented by the general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (wherein X is a hydrogen atom or chlorine atom, and R is a methyl group or ethyl group) The herbicide according to claim 1. 4 General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X is a hydrogen atom or a chlorine atom, Y is a nitro group, cyano group, or halogen atom, and R is a hydrogen atom or a lower alkyl group) A phenoxyphenoxyalkane nitrile derivative represented by: 5. Phenoxyphenoxy according to claim 4, which is represented by the general formula ▲ There are numerical formulas, chemical formulas, tables, etc. Alkane nitrile derivative. 6. Phenoxyphenoxy according to claim 4, which is represented by the general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (in the formula, X is a hydrogen atom or a chlorine atom, and R is a methyl group or an ethyl group) Alkane nitrile derivative.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2308476A JPS5934705B2 (en) | 1976-03-05 | 1976-03-05 | Phenoxyphenoxyalkane nitrile derivatives and herbicides containing them |
| NZ181994A NZ181994A (en) | 1975-09-27 | 1976-09-09 | (2-chloro-4-trifluorom-ethylphenoxy)-phenoxy acids,esters,ethers,amides and nitriles and herbicidal compositions |
| US05/722,327 US4070177A (en) | 1975-09-27 | 1976-09-10 | Herbicidal phenoxy-phenoxy alkane carboxylic acid derivatives |
| GB38458/76A GB1497520A (en) | 1975-09-27 | 1976-09-16 | Substituted 3-phenoxy phenoxy alkane carboxylic acids nitriles esters and amides and herbicidal compositions thereo |
| AU17909/76A AU501045B2 (en) | 1975-09-27 | 1976-09-20 | Phenoxyphenoxyalkanr carboxlic acid derivatives |
| FR7628996A FR2325638A1 (en) | 1975-09-27 | 1976-09-27 | PHENOXY PHENOXY ALKANE CARBOXYLIC ACID HERBICIDES |
| DE2643438A DE2643438C2 (en) | 1975-09-27 | 1976-09-27 | Phenoxyphenoxyalkanecarboxylic acid derivatives and herbicides containing them |
| CA262,067A CA1101435A (en) | 1975-09-27 | 1976-09-27 | Herbicide |
| US05/837,815 US4203758A (en) | 1975-09-27 | 1977-09-29 | Herbicidal phenoxy-phenoxyalkane thio esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2308476A JPS5934705B2 (en) | 1976-03-05 | 1976-03-05 | Phenoxyphenoxyalkane nitrile derivatives and herbicides containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS52108938A JPS52108938A (en) | 1977-09-12 |
| JPS5934705B2 true JPS5934705B2 (en) | 1984-08-24 |
Family
ID=12100541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2308476A Expired JPS5934705B2 (en) | 1975-09-27 | 1976-03-05 | Phenoxyphenoxyalkane nitrile derivatives and herbicides containing them |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5934705B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6337108U (en) * | 1986-08-28 | 1988-03-10 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52111526A (en) * | 1976-03-17 | 1977-09-19 | Mitsui Toatsu Chem Inc | Novel diphenylethers and herbicides containing the same |
| CH626318A5 (en) * | 1977-03-08 | 1981-11-13 | Ciba Geigy Ag | |
| DE2961372D1 (en) * | 1978-01-20 | 1982-01-28 | Ciba Geigy Ag | Phenoxy-phenoxy-alkylcarboxylic acid derivatives with herbicidal activity, their preparation, compositions containing them and their use |
-
1976
- 1976-03-05 JP JP2308476A patent/JPS5934705B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6337108U (en) * | 1986-08-28 | 1988-03-10 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52108938A (en) | 1977-09-12 |
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