JPS6154017B2 - - Google Patents
Info
- Publication number
- JPS6154017B2 JPS6154017B2 JP7021079A JP7021079A JPS6154017B2 JP S6154017 B2 JPS6154017 B2 JP S6154017B2 JP 7021079 A JP7021079 A JP 7021079A JP 7021079 A JP7021079 A JP 7021079A JP S6154017 B2 JPS6154017 B2 JP S6154017B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- present
- weight
- compound
- parts
- 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
- 230000002363 herbicidal effect Effects 0.000 claims description 17
- 239000004009 herbicide Substances 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- PIZLNJQSSMQFOE-UHFFFAOYSA-N n,2-diphenylpropanamide Chemical compound C=1C=CC=CC=1C(C)C(=O)NC1=CC=CC=C1 PIZLNJQSSMQFOE-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 18
- 241000196324 Embryophyta Species 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- AWZJXXWDKOAELM-UHFFFAOYSA-N 2-phenyl-n-[3-(trifluoromethyl)phenyl]acetamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)CC=2C=CC=CC=2)=C1 AWZJXXWDKOAELM-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000234653 Cyperus Species 0.000 description 5
- 241000209094 Oryza Species 0.000 description 5
- 244000184734 Pyrus japonica Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- -1 m-trifluoromethylphenylacetyl halide Chemical class 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 241000254158 Lampyridae Species 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000218691 Cupressaceae Species 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- FEVJJJQOPGZSIG-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenyl]acetyl chloride Chemical compound FC(F)(F)C1=CC=CC(CC(Cl)=O)=C1 FEVJJJQOPGZSIG-UHFFFAOYSA-N 0.000 description 1
- MKFHVRPIJCVSLK-UHFFFAOYSA-N 3,3,3-trifluoro-2-phenylpropanamide Chemical compound NC(=O)C(C(F)(F)F)C1=CC=CC=C1 MKFHVRPIJCVSLK-UHFFFAOYSA-N 0.000 description 1
- HQRSIMQXCAWAJB-UHFFFAOYSA-N 3,3,3-trifluoro-2-phenylpropanoic acid Chemical compound OC(=O)C(C(F)(F)F)C1=CC=CC=C1 HQRSIMQXCAWAJB-UHFFFAOYSA-N 0.000 description 1
- 241000254032 Acrididae Species 0.000 description 1
- 235000003840 Amygdalus nana Nutrition 0.000 description 1
- 244000296825 Amygdalus nana Species 0.000 description 1
- 240000008853 Datura stramonium Species 0.000 description 1
- 241001076438 Oxya japonica Species 0.000 description 1
- 235000011432 Prunus Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 240000000260 Typha latifolia Species 0.000 description 1
- 235000005324 Typha latifolia Nutrition 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000014774 prunus Nutrition 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011076 safety test Methods 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
Description
本発明は、特に多年性雑草に対する除草作用を
有する新規なｍ―トリフルオロメチルフエニルア
セタニリド及びｍ―トリフルオロメチルフエニル
アセタニリドを有効成分とする除草剤に関するも
のである。
これまで、トリフルオロメチルフエニル酢酸及
びトリフルオロメチルフエニルアセタミドがオナ
モミ、イチビ、ジムソン・ウイードなどの雑草に
対して除草作用を示し、畑作用除草剤として有用
であることは知られている（特公昭46−34999号
公報）。
しかしながら、これらの化合物は、近年問題と
なつているホタルイ、ミズガヤツリ、ウリカワな
どの多年性雑草に対する除草作用は十分とはいえ
ず、したがつて、水田用除草剤として満足できる
ものとはいえなかつた。
本発明者は、このような多年性雑草に対して除
草作用を示し、水田用除草剤としてすぐれている
化合物を得るべく鋭意研究を重ねた結果、ｍ―ト
リフルオロメチルフエニルアセタニリドが特に多
年性雑草や広葉系雑草に対する根部抑制作用が大
であることを見出し、この知見に基づいて本発明
をなすに至つた。
すなわち、本発明は、一般式（）
（式中のＲは水素原子、ハロゲン原子、低級アル
キル基、低級アルコキシ基、トリフルオロメチル
基、ニトロ基、カルボキシル基、アミノ基、ジメ
チルアミノ基又は水酸基を意味する）
で表わされるｍ―トリフルオロメチルフエニルア
セタニリド及びこのｍ―トリフルオロメチルフエ
ニルアセタニリドを有効成分とする除草剤を提供
するものである。
本発明の化合物は、いずれも文献未載の新規化
合物であり、たとえばｍ―トリフルオロメチルフ
エニルアセチルハライドを有機溶媒中で塩基の存
在下に、一般式（）
（式中のＲは前記の意味を有する）
で表わされる芳香族アミンと反応させることによ
つて製造することができる。
この反応においてｍ―トリフルオロメチルフエ
ニルアセチルハライドと一般式（）で表わされ
る芳香族アミノとの割合は等モルあるいはｍ―ト
リフルオロメチルフエニルアセチルハライドをや
や過剰モル用いるのが好ましい。
また、脱ハロゲン化水素剤として使用する塩基
は、有機塩基及び無機塩基のいずれでもよい。
反応温度は10〜50℃が好ましく、反応時間は３
時間以内で十分である。
このようにして得られる反応混合物を冷水にあ
け、有機溶媒で抽出し水洗した後乾燥し、有機溶
媒を蒸発させて得られる残留物を再結晶すること
により目的とする本発明の化合物を高純度で得る
ことができる。
本発明の化合物は、その赤外線スペクトルが
3280cm-1付近において−NH−、1600cm-1付近に
おいて−NHCO−に由来する特性吸収を有し、核
磁気共鳴スペクトルが3.58（ｓ）ppmにおいて−
CH2−に由来する特性吸収を有するのでその化学
構造を確認することができる。
本発明の化合物は、近年問題となつているホタ
ルイ、ミズガヤツリ、ウリカワなどの多年性雑草
の根部の伸長を著しく阻害することによつて、そ
の生長を抑制するもので、その除草作用は、上記
雑草の種子に対しても、塊莖に対しても強力であ
る。また、本発明の化合物は稲に対して安全性が
極めて高いので、稲作用除草剤として特に有用で
あるが、各種殻類、そ菜類、芝生、牧草地、果樹
園、茶園、森林地、非農耕地などの除草剤として
使用することもできる。使用量は、有効成分量で
50〜1000ｇ／10a、特に100〜500ｇ／10aの範囲が
好ましい。
本発明のｍ―トリフルオロメチルフエニルアセ
タニリドを含有する除草剤は、他の農薬、たとえ
ば、殺虫剤、殺菌剤、従来公知の除草剤、生長調
節剤など、又は肥料を含有していてもよく、ある
いはこれらと混合して使用されてもよい。
本発明の除草剤は、常法の除草剤製剤法に準じ
て、水和剤、乳剤又は粒剤の形態をとることもで
きる。
次に、実施例により本発明をさらに詳細に説明
する。
実施例 １
ｍ―トリフルオロメチルフエニルアセタニリド
類の製造
ｍ―アニシジン6.6ｇ（54.0mmol）をベンゼン
100mlに溶かし、室温でかきまぜながら、この中
にｍ―トリフルオロメチルフエニルアセチルクロ
リド6.0ｇ（27.0mmol）を15分かけて滴下し、そ
の後１時間かきまぜた。反応終了後、反応混合物
を冷水にあけ、酢酸エチル100mlで抽出した。抽
出液を水洗した後無水芒硝で乾燥し、酢酸エチル
を留去させて得られる残留物をベンゼン―ヘキサ
ン（１：１）の混合溶媒から再結晶すると無色針
状結晶として、3′―メトキシ―ｍ―トリフルオロ
メチルフエニルアセタニリド（第１表における化
合物１）7.0ｇ（収率83.3％）が得られた。
IR（−NH−3280cm-1、−NHCO−1600cm-1、in
KBr）及びNMR（−CH2−3.58（ｓ）ppm、−
OCH33.55（ｓ）ppm、in CDCl3）により、その
化学構造を確認した。
同様にして第１表に示す各種のｍ―トリフルオ
ロメチルフエニルアセタニリドを製造し、IR及
びNMRでその化学構造を確認した。
The present invention relates to a novel m-trifluoromethylphenylacetanilide and a herbicide containing m-trifluoromethylphenylacetanilide as an active ingredient, which has a herbicidal effect on perennial weeds in particular. Until now, it has been known that trifluoromethylphenylacetic acid and trifluoromethylphenylacetamide have a herbicidal effect on weeds such as Japanese grasshopper, grasshopper, and jimson weed, and are useful as field herbicides. (Special Publication No. 46-34999). However, these compounds cannot be said to have sufficient herbicidal activity against perennial weeds such as firefly, cypress, and weed, which have become a problem in recent years, and therefore cannot be said to be satisfactory as herbicides for paddy fields. . As a result of intensive research to obtain a compound that exhibits herbicidal activity against such perennial weeds and is excellent as a herbicide for paddy fields, the present inventor found that m-trifluoromethylphenylacetanilide is particularly effective. It was discovered that the root control effect on perennial weeds and broad-leaved weeds is significant, and based on this knowledge, the present invention was accomplished. That is, the present invention provides the general formula () (R in the formula means a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a trifluoromethyl group, a nitro group, a carboxyl group, an amino group, a dimethylamino group, or a hydroxyl group) The present invention provides a herbicide containing methylphenylacetanilide and m-trifluoromethylphenylacetanilide as an active ingredient. The compounds of the present invention are all novel compounds that have not been described in any literature. For example, m-trifluoromethylphenylacetyl halide is prepared by the general formula () (R in the formula has the above-mentioned meaning) It can be produced by reacting with an aromatic amine represented by the following. In this reaction, m-trifluoromethylphenylacetyl halide and the aromatic amino represented by the general formula () are preferably used in equimolar ratios, or m-trifluoromethylphenylacetyl halide is preferably used in a slightly excess molar amount. Furthermore, the base used as the dehydrohalogenating agent may be either an organic base or an inorganic base. The reaction temperature is preferably 10-50℃, and the reaction time is 3
It is enough within the hour. The reaction mixture thus obtained is poured into cold water, extracted with an organic solvent, washed with water, dried, and the organic solvent is evaporated. The resulting residue is recrystallized to obtain the desired compound of the present invention with high purity. You can get it at The compound of the present invention has an infrared spectrum of
It has a characteristic absorption derived from -NH- near 3280 cm -1 and -NHCO- near 1600 cm -1 , and the nuclear magnetic resonance spectrum shows - at 3.58 (s) ppm.
Since it has a characteristic absorption derived from CH 2 −, its chemical structure can be confirmed. The compound of the present invention suppresses the growth of perennial weeds such as firefly, cypress, and weed, which have become a problem in recent years, by significantly inhibiting their growth. It is powerful against both seeds and tubercles. In addition, the compounds of the present invention are extremely safe for rice, so they are particularly useful as herbicides for rice cultivation. It can also be used as a herbicide on agricultural land. The amount used is based on the amount of active ingredient.
A range of 50 to 1000 g/10a, particularly 100 to 500 g/10a is preferred. The herbicide containing m-trifluoromethylphenylacetanilide of the present invention does not contain other agricultural chemicals, such as insecticides, fungicides, conventionally known herbicides, growth regulators, etc., or fertilizers. or may be used in combination with these. The herbicide of the present invention can also be in the form of a wettable powder, emulsion, or granule according to conventional herbicide formulation methods. Next, the present invention will be explained in more detail with reference to Examples. Example 1 Production of m-trifluoromethylphenylacetanilides 6.6 g (54.0 mmol) of m-anisidine was added to benzene.
The solution was dissolved in 100 ml, and while stirring at room temperature, 6.0 g (27.0 mmol) of m-trifluoromethylphenylacetyl chloride was added dropwise over 15 minutes, followed by stirring for 1 hour. After the reaction was completed, the reaction mixture was poured into cold water and extracted with 100 ml of ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and ethyl acetate was distilled off. The resulting residue was recrystallized from a mixed solvent of benzene-hexane (1:1) to form colorless needle-like crystals. 7.0 g (yield 83.3%) of m-trifluoromethylphenylacetanilide (compound 1 in Table 1) was obtained. IR (−NH−3280cm −1 , −NHCO−1600cm −1 , in
KBr) and NMR (-CH 2 -3.58(s) ppm, -
The chemical structure was confirmed by OCH 3 3.55 (s) ppm, in CDCl 3 ). In the same manner, various m-trifluoromethylphenylacetanilides shown in Table 1 were produced, and their chemical structures were confirmed by IR and NMR.
【表】【table】
【表】【table】
【表】
実施例 ２
水和剤、乳剤及び粒剤の調製
(1) 第１表における化合物(1)40重量部、ジークラ
イトとクニライト（共に商品名：国峰社製、粘
土鉱物）の２：１混合物55重量部、ソルボール
800（商品名：東邦化学工業製、界面活性剤）
５重量部を混合粉砕して、40重量％水和剤を得
た。
(2) 第１表における化合物(2)25重量部、ベンゼン
65重量部、ソルボール800 10重量部を混合溶解
して、25重量％乳剤を得た。
(3) 第１表における化合物(5)５重量部、ベントナ
イト50重量部、クニライト40重量部、ソルボー
ル800 ５重量部を混合粉砕したのち、水10重量
部を加えて均一にかきまぜてペースト状とし、
直径0.7mmの篩穴から押し出して乾燥してから
１〜２mmの長さに切断して５重量％粒剤を得
た。
実施例 ３
ホタルイ、キカジグサに対する除草試験及び水
稲に対する安全性試験
直径15cmのポツトに水田土壤を入れてホタルイ
及びキカジグサの種子を播種した。さらに３葉期
の水稲苗２本１株として２cmの深さに移植した。
２cmの湛水後本発明の化合物の水和剤を10mlの水
に希釈して水面に均一に処理した。
調査は、処理してから２週間後に行つた。
結果を第２表に示す。
第２表に於いて化合物の番号は第１表における
化合物の番号に対応している。
除草効果の評価は０：正常、10：完全防除の10
段階とし、水稲薬害は−：無害〜〓大害として表
示した。[Table] Example 2 Preparation of wettable powders, emulsions, and granules (1) 40 parts by weight of the compound (1) in Table 1, 2 of ziecrite and cunylite (both trade names: manufactured by Kokuhosha, clay minerals): 1 mixture 55 parts by weight, Solbol
800 (Product name: Toho Chemical Co., Ltd., surfactant)
5 parts by weight were mixed and ground to obtain a 40% by weight wettable powder. (2) 25 parts by weight of compound (2) in Table 1, benzene
65 parts by weight and 10 parts by weight of Solbol 800 were mixed and dissolved to obtain a 25% by weight emulsion. (3) Mix and grind 5 parts by weight of compound (5) in Table 1, 50 parts by weight of bentonite, 40 parts by weight of Kunilite, and 5 parts by weight of Solbol 800, then add 10 parts by weight of water and stir evenly to form a paste. ,
It was extruded through a sieve hole with a diameter of 0.7 mm, dried, and then cut into lengths of 1 to 2 mm to obtain 5% by weight granules. Example 3 Herbicidal test on firefly and Kikajigusa and safety test on paddy rice Rice field soil was placed in a pot with a diameter of 15 cm, and seeds of Bulrush and Kikajigusa were sown. Furthermore, two paddy rice seedlings at the three-leaf stage were transplanted as one plant to a depth of 2 cm.
After immersion in water to a depth of 2 cm, a hydrating agent of the compound of the present invention was diluted in 10 ml of water and applied uniformly to the water surface. The study was conducted two weeks after treatment. The results are shown in Table 2. The compound numbers in Table 2 correspond to the compound numbers in Table 1. The evaluation of herbicidal effect is 0: normal, 10: complete control.
The paddy rice damage was classified as -: harmless to severe damage.
【表】【table】
【表】【table】
【表】
実施例 ４
ウリカワ及びミズガヤツリに対する除草試験
直径15cmのポツトに水田土壤を入れ、ウリカワ
及びミズガヤツリの塊莖各３個を移植した。２cm
の湛水後に本発明化合物の所定薬量を10mlの水に
希釈して水面に適下処理した。
処理してから20日後に地上部及び地下部の長さ
を測定し、無処区と同等を０とし、完全抑制を10
として表わした。
結果を第３表に示す。
第３表において、本発明化合物の番号は、第１
表における化合物の番号に対応している。
第３表から、多年性雑草であるウリカワ及びミ
ズガヤツリに対して、市販除草剤であるベンチオ
カーブはほとんど除草効果を示さないが、本発明
化合物は、いずれも強力な除草効果を示すことが
判る。[Table] Example 4 Weeding test on Cyperus japonica and Cyperus japonica Paddy soil was placed in a pot with a diameter of 15 cm, and three clumps each of Cyperus japonica and Cyperus japonica were transplanted. 2cm
After flooding, a predetermined amount of the compound of the present invention was diluted in 10 ml of water and applied to the water surface. 20 days after treatment, the length of the aboveground and underground parts was measured, and 0 was equivalent to the untreated area, and 10 was complete suppression.
It was expressed as The results are shown in Table 3. In Table 3, the numbers of the compounds of the present invention are
Corresponds to the compound number in the table. Table 3 shows that the commercially available herbicide bentiocarb has almost no herbicidal effect on the perennial weeds Prunus elegans and Cyperus japonica, but the compounds of the present invention all have a strong herbicidal effect.
【表】【table】
【表】
オールカーバメート
[Table] All carbamates
Claims (1)
キル基、低級アルコキシ基、トリフルオロメチル
基、ニトロ基、カルボキシル基、アミノ基、ジメ
チルアミノ基又は水酸基を意味する） で表わされるｍ―トリフルオロメチルフエニルア
セタニリド。 ２ 一般式 （式中のＲは水素原子、ハロゲン原子、低級アル
キル基、低級アルコキシ基、トリフルオロメチル
基、ニトロ基、カルボキシル基、アミノ基、ジメ
チルアミノ基又は水酸基を意味する） で表わされるｍ―トリフルオロメチルフエニルア
セタニリドを有効成分とする除草剤。[Claims] 1. General formula (R in the formula means a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a trifluoromethyl group, a nitro group, a carboxyl group, an amino group, a dimethylamino group, or a hydroxyl group) Methylphenyl acetanilide. 2 General formula (R in the formula means a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a trifluoromethyl group, a nitro group, a carboxyl group, an amino group, a dimethylamino group, or a hydroxyl group) A herbicide whose active ingredient is methylphenylacetanilide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7021079A JPS55162757A (en) | 1979-06-05 | 1979-06-05 | Meta-trifluoromethylphenylacetanilide and herbicide contaning it as active constituent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7021079A JPS55162757A (en) | 1979-06-05 | 1979-06-05 | Meta-trifluoromethylphenylacetanilide and herbicide contaning it as active constituent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55162757A JPS55162757A (en) | 1980-12-18 |
| JPS6154017B2 true JPS6154017B2 (en) | 1986-11-20 |
Family
ID=13424924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7021079A Granted JPS55162757A (en) | 1979-06-05 | 1979-06-05 | Meta-trifluoromethylphenylacetanilide and herbicide contaning it as active constituent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55162757A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS599521B2 (en) * | 1981-03-03 | 1984-03-03 | 八洲化学工業株式会社 | herbicide |
| JPS60136546A (en) * | 1983-12-26 | 1985-07-20 | Yashima Chem Ind Co Ltd | Substituted phenylacetanilide derivative, its production and use thereof |
| WO1997045400A1 (en) | 1996-05-24 | 1997-12-04 | Neurosearch A/S | Phenyl derivatives containing an acidic group, their preparation and their use as chloride channel blockers |
| EP1033366A3 (en) * | 1999-02-18 | 2000-12-27 | Pfizer Products Inc. | Amide derivatives useful as Neuropeptide Y (NPY) antagonists |
| US6407120B1 (en) | 1999-02-18 | 2002-06-18 | Pfizer Inc. | Neuropeptide Y antagonists |
-
1979
- 1979-06-05 JP JP7021079A patent/JPS55162757A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55162757A (en) | 1980-12-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6087254A (en) | Novel urea compound and herbicide containing the same | |
| JPS6254301B2 (en) | ||
| JPS6154017B2 (en) | ||
| JPH0360823B2 (en) | ||
| JPS6254302B2 (en) | ||
| JPS61221170A (en) | Trifluoromethanesulfonylamide derivative and herbicide containing said derivative as active component | |
| JPS5842864B2 (en) | N-(α,α-dialkylbenzyl)phenylacetamide derivatives and herbicides containing the same | |
| JPS6130671B2 (en) | ||
| KR830001714B1 (en) | Process for the preparation of diphenyl ether derivatives | |
| JPS5938222B2 (en) | substituted phenyl urea | |
| JPS58219167A (en) | Substituted phenylhydantoin derivative, its preparation, and herbicide comprising it as active ingredient | |
| JPS59130847A (en) | Alpha,alpha-methylethylphenylacetic anilide derivative, its preparation and herbicide containing the same | |
| JPS6041648A (en) | Alpha,alpha-dimethylphenylacetic acid anilide derivative, its preparation, and herbicide containing it | |
| JPS6011482A (en) | Thiadiazinone derivative and herbicide | |
| JPH0142262B2 (en) | ||
| JPS6042376A (en) | N-(2,3-epoxypropylene) sulfonamide derivative and selective herbicide containing it as active ingredient | |
| JPS6150948A (en) | N-substituted-chloroacetamide | |
| JPS6223748B2 (en) | ||
| JPS5843943A (en) | N-(alpha,alpha-dimethylbenzyl)phenylacetamide derivative and herbicide containing the same | |
| JPS59155366A (en) | Amide derivative, its preparation, and herbicide | |
| JPS5928530B2 (en) | Substituted phenyl ureas and herbicides for rice fields | |
| JPS6157304B2 (en) | ||
| JPS58150548A (en) | Alpha-amino fatty acid anilide derivative and preparation thereof and herbicide | |
| JPS5953466A (en) | N-phenyltetrahydrophthalimide derivative, its preparation and herbicide containing said derivative as active component | |
| JPS6056944A (en) | Chloroacetamide derivative, preparation thereof and herbicide containing the same as active constituent |