JPS6260389B2 - - Google Patents
Info
- Publication number
- JPS6260389B2 JPS6260389B2 JP10793285A JP10793285A JPS6260389B2 JP S6260389 B2 JPS6260389 B2 JP S6260389B2 JP 10793285 A JP10793285 A JP 10793285A JP 10793285 A JP10793285 A JP 10793285A JP S6260389 B2 JPS6260389 B2 JP S6260389B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- acid amide
- pentenoic acid
- amide derivative
- compound
- 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 20
- 239000004009 herbicide Substances 0.000 claims description 10
- MZDYAVCNKNXCIS-UHFFFAOYSA-N pent-2-enamide Chemical class CCC=CC(N)=O MZDYAVCNKNXCIS-UHFFFAOYSA-N 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 description 36
- 239000000203 mixture Substances 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 14
- 238000009472 formulation Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 241000218691 Cupressaceae Species 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- 239000008187 granular material Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000004927 clay Substances 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000000887 hydrating effect Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- KDNCGADQPWREDS-UHFFFAOYSA-N 4-bromopent-2-enoic acid Chemical class CC(Br)C=CC(O)=O KDNCGADQPWREDS-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000237515 Chlamys nipponensis Species 0.000 description 1
- 241000931705 Cicada Species 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 235000008247 Echinochloa frumentacea Nutrition 0.000 description 1
- 241000254158 Lampyridae Species 0.000 description 1
- 241001076438 Oxya japonica Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 235000005324 Typha latifolia Nutrition 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 244000118869 coast club rush Species 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- PHHWLDOIMGFHOZ-UHFFFAOYSA-L disodium;dinaphthalen-1-ylmethanedisulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)(S(=O)(=O)[O-])S([O-])(=O)=O)=CC=CC2=C1 PHHWLDOIMGFHOZ-UHFFFAOYSA-L 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011812 mixed powder Substances 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- -1 polyoxyethylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
〔産業上の利用分野〕
この発明は新規かつ有用な２−ペンテン酸アミ
ド誘導体、およびこれを有効成分として含有する
除草剤に関するものである。
〔従来の技術〕
従来、２−ペンテン酸アミド誘導体に近い物質
として、４−ブロム−２−ペンテン酸ならびにそ
のエステル誘導体がケミカルアブストラクト第47
巻3798g、第50巻6465l、第55巻1420b、第65巻Ｐ
−16912b等に記載されている。
〔発明が解決しようとする問題点〕
しかしながら上記のような従来の物質の生理活
性については不明であり、またこれらの公知物質
は除草活性を示さない。
また近年多くの除草剤が実用化されるに至り、
農作業の軽減化、効率化、あるいは農作物の保護
に役立つているが、一方では農薬による環境汚染
も大きな問題となつている。そこで少量の薬量で
有害雑草あるいは有害病原菌に有効に作用し、し
かも環境汚染のない高度に安全な薬剤の開発が望
まれている。
〔問題点を解決するための手段〕
本発明者等はこれらの要望に答えるべく鋭意研
究を重ねた結果、文献末記載の新規な２−ペンテ
ン酸アミド誘導体が優れた除草活性を有すること
を見出し本発明を完成したものである。
本発明は式
（式中、R1およびR2は炭素数１〜４の低級アルキ
ル基を示し、R3は低級アルコキシ基または低級
アルキルチオ基を示し、Ｘはハロゲン原子を示
し、Ｙは酸素原子またはイオウ原子を示し、ｎは
１〜２の整数を示す。）
にて表わされる２−ペンテン酸アミド誘導体およ
びこれを有効成分として含有する新規な除草剤で
ある。
本発明の代表的化合物ならびに物理定数（屈折
率）を表１に示す。表１中の化合物番号は以後の
記載において参照される。
[Industrial Application Field] This invention relates to a new and useful 2-pentenoic acid amide derivative and a herbicide containing the same as an active ingredient. [Prior Art] Conventionally, 4-bromo-2-pentenoic acid and its ester derivatives have been reported in Chemical Abstracts No. 47 as substances similar to 2-pentenoic acid amide derivatives.
Volume 3798g, Volume 50 6465l, Volume 55 1420b, Volume 65P
-16912b etc. [Problems to be Solved by the Invention] However, the physiological activity of the above-mentioned conventional substances is unknown, and these known substances do not exhibit herbicidal activity. In addition, many herbicides have come into practical use in recent years.
Although they are useful for reducing agricultural work, improving efficiency, and protecting crops, environmental pollution caused by pesticides has also become a major problem. Therefore, there is a desire to develop a highly safe drug that effectively acts on noxious weeds or harmful pathogens in small doses and does not pollute the environment. [Means for Solving the Problems] As a result of intensive research to meet these demands, the present inventors discovered that a novel 2-pentenoic acid amide derivative described at the end of the literature has excellent herbicidal activity. This completes the present invention. The present invention is based on the formula (In the formula, R 1 and R 2 represent a lower alkyl group having 1 to 4 carbon atoms, R 3 represents a lower alkoxy group or a lower alkylthio group, X represents a halogen atom, and Y represents an oxygen atom or a sulfur atom. and n is an integer of 1 to 2) and a novel herbicide containing the same as an active ingredient. Representative compounds of the present invention and physical constants (refractive index) are shown in Table 1. Compound numbers in Table 1 are referred to in the following description.
以上のとおり、本発明は新規かつ有用な化合物
および除草剤であり、その薬効ならびに作物に対
する安全性は極めて高い。
〔実施例〕
以下本発明の化合物を有効成分とする製剤の配
合例を挙げるが、本発明の除草剤はこの範囲に限
定されるものではなく、除草活性の表われる範囲
で配合の変更を行うことができる。なお、各配合
例中％は重量％、部は重量部を示す。
配合例 １
粉 剤
化合物(1)４％、珪藻土５％およびクレー91％を
均一に混合粉砕して粉剤とする。
配合例 ２
水和剤
化合物(2)50％、珪藻土45％、ジナフチルメタン
ジスルホン酸ナトリウム２％およびリグニンスル
ホン酸ナトリウム３％を均一に混合粉砕して水和
剤とする。
配合例 ３
乳 剤
化合物(3)30％、シクロヘキサノン20％、ポリオ
キシエチレンアルキルアリールエーテル11％、ア
ルキルベンゼンスルホン酸カルシウム４％および
メチルナフタレン35％を均一に溶解して乳剤とす
る。
配合例 ４
微粒剤
60〜250メツシユの海砂96部にポリエチレング
リコール４部を添加して激しく混合し、ポリエチ
レングリコールを海砂の表面に均一に付着させ
る。この混合物94％に化合物(4)とクレーの混和粉
末（混合比７：３）６％を加え激しく混合して微
粒剤とする。
配合例 ５
粒 剤
化合物(3)５％、ラウリルアルコール硫酸エステ
ルのナトリウム塩２％、リグニンスルホン酸ナト
リウム５％、カルボキシメチルセルロース２％お
よびクレー86％を均一に混合粉砕する。この混合
物80部に対して水20部を加えて練合させ、押出式
造粒機で14〜32メツシユの粒状に加工後、乾燥し
て粒剤とする。
次に本発明化合物の効果を試験例を以つて説明
する。
試験例 １
移植直後における湛水土壌処理試験１／5000a
のワグネルポツトに水田土壌を充填し、代掻後、
タイヌビエ、タマガヤツリ、コナギの種子を播種
した。また３葉期の水稲苗（品種：金南風）を１
株２本として２株移植し、３cmに湛水した。次に
配合例２に準じて調製した表２の本発明化合物お
よび比較化合物の水和剤を、各化合物の有効成分
量が表２の所定量になるよう水で希釈し、水面に
滴下処理した。その後温室内に静置し、処理20日
目に除草効果および水稲におよぼす影響を調査し
た。結果を、除草効果または薬害の程度を表わす
効果指数により表２に示す。効果指数は次式
除草効果（薬害）
＝無処理区生体重−処理区生体重／無処理区生体重×
100
により除草効果または薬剤（％）を算出し、次の
基準により決定した。
As described above, the present invention is a novel and useful compound and herbicide, and its medicinal efficacy and safety for crops are extremely high. [Example] Examples of formulations of preparations containing the compound of the present invention as an active ingredient are listed below, but the herbicide of the present invention is not limited to this range, and the formulation may be changed within the range that exhibits herbicidal activity. be able to. In each formulation example, % indicates weight %, and parts indicate parts by weight. Formulation Example 1 Powder 4% of compound (1), 5% of diatomaceous earth and 91% of clay are uniformly mixed and ground to obtain a powder. Formulation Example 2 Wettable powder A wettable powder is prepared by uniformly mixing and pulverizing 50% of compound (2), 45% of diatomaceous earth, 2% of sodium dinaphthylmethane disulfonate, and 3% of sodium ligninsulfonate. Formulation Example 3 Emulsion 30% of compound (3), 20% of cyclohexanone, 11% of polyoxyethylene alkylaryl ether, 4% of calcium alkylbenzenesulfonate and 35% of methylnaphthalene are uniformly dissolved to prepare an emulsion. Formulation Example 4 Fine Granules Add 4 parts of polyethylene glycol to 96 parts of 60-250 mesh sea sand and mix vigorously to uniformly adhere the polyethylene glycol to the surface of the sea sand. Add 6% of a mixed powder of compound (4) and clay (mixing ratio 7:3) to 94% of this mixture and mix vigorously to obtain fine granules. Formulation Example 5 Granules 5% of compound (3), 2% of sodium salt of lauryl alcohol sulfate, 5% of sodium lignin sulfonate, 2% of carboxymethylcellulose and 86% of clay are uniformly mixed and ground. 20 parts of water is added to 80 parts of this mixture and kneaded, processed into 14 to 32 mesh granules using an extrusion granulator, and dried to form granules. Next, the effects of the compounds of the present invention will be explained using test examples. Test example 1 Flooded soil treatment test 1/5000a immediately after transplanting
After filling the Wagner pot with paddy soil and puddling,
Seeds of Japanese millet, Japanese cypress, and Japanese cypress were sown. In addition, 1 paddy rice seedling (variety: Kinnanfu) at the 3-leaf stage
Two plants were transplanted as two plants and submerged in water to a depth of 3 cm. Next, the hydrating agents of the compounds of the present invention and comparative compounds in Table 2 prepared according to Formulation Example 2 were diluted with water so that the amount of active ingredient of each compound became the prescribed amount in Table 2, and the mixture was dropped onto the water surface. . Thereafter, the mixture was left in a greenhouse, and on the 20th day of treatment, the herbicidal effect and the effect on paddy rice were investigated. The results are shown in Table 2 using an efficacy index representing the degree of herbicidal effect or phytotoxicity. The effectiveness index is calculated using the following formula: herbicidal effect (chemical damage) = untreated area fresh weight - treated area fresh weight / untreated area fresh weight x
The herbicidal effect or drug (%) was calculated based on 100 and determined based on the following criteria.
【表】
なお比較のために試験した比較化合物は次の通
りである。
比較化合物１（ケミカルアブストラクト第65巻Ｐ
−16912b記載化合物）
比較化合物２（ケミカルアブストラクト第47巻
3798g記載化合物）
比較化合物３（ケミカルアブストラクト第50巻
6465l記載化合物）
比較化合物４（特開昭52−18822号公報記載化合
物）
比較化合物５（特開昭52−18822号公報記載化合
物）
比較化合物６（特開昭54−5005号公報記載化合
物）
比較化合物７（特開昭54−5005号公報記載化合
物）
比較化合物８（特開昭54−5005号公報記載化合
物）
比較化合物９（特開昭54−5005号公報記載化合
物）
[Table] Comparative compounds tested for comparison are as follows. Comparative Compound 1 (Chemical Abstracts Vol. 65 P
−16912b listed compounds) Comparative Compound 2 (Chemical Abstracts Vol. 47)
3798g listed compound) Comparative Compound 3 (Chemical Abstracts Vol. 50)
6465l listed compounds) Comparative compound 4 (compound described in JP-A-52-18822) Comparative compound 5 (compound described in JP-A-52-18822) Comparative compound 6 (compound described in JP-A-54-5005) Comparative compound 7 (compound described in JP-A-54-5005) Comparative compound 8 (compound described in JP-A-54-5005) Comparative compound 9 (compound described in JP-A-54-5005)
【表】【table】
【表】
試験例 ２
発芽前多年生雑草に対する効果
１／5000aのワグネルポツトに水田土壌を充填
し、代掻後ホタルイ、ヘラオモダカの種子を播種
した。播種翌日の配合例２に準じて調製した表３
の本発明化合物および比較化合物の水和剤を、各
化合物の有効成分量が表３の所定量になるよう水
で希釈し、水面に滴下処理した。その後温室内に
静置し、20日目に試験例１に示した効果指数によ
り除草効果を評価した結果を表３に示す。[Table] Test Example 2 Effect on pre-germinated perennial weeds A 1/5000a Wagner pot was filled with paddy soil, and after puddling, the seeds of bulrush and cicada were sown. Table 3 prepared according to Formulation Example 2 on the day after sowing
Wettable powders of the compounds of the present invention and comparative compounds were diluted with water so that the amount of active ingredient of each compound was the predetermined amount shown in Table 3, and the diluted powders were dropped onto the water surface. Thereafter, it was allowed to stand in a greenhouse, and on the 20th day, the herbicidal effect was evaluated using the effectiveness index shown in Test Example 1. Table 3 shows the results.
【表】【table】
【表】
試験例 ３
葉令の進んだ水田雑草に対する除草効果
１／5000aのワグネルポツトに水田土壌を充填
し、代掻後ノビエ、タマガヤツリ、コナギ、ホタ
ルイ、ヘラオモダカの種子を播種した。播種10日
後に配合例２に準じて調製した表４の本発明化合
物および比較化合物の水和剤を、各化合物の有効
成分量が表４の所定量になるよう水で希釈し、水
面に滴下処理した。その後温室内に静置し、処理
20日目に試験例１に示した効果指数により除草効
果を評価した結果を表４に示す。なお薬剤処理時
の各雑草の葉令は、ノビエ、タマガヤツリ、コナ
ギが１葉期、ホタルイ、ヘラオモダカが0.5〜１
葉期であつた。[Table] Test Example 3 Herbicidal effect on paddy field weeds with advanced leaf age A 1/5000a Wagner pot was filled with paddy soil, and after puddling, seeds of Japanese grasshopper, Japanese cypress, Japanese cypress, Japanese scallop, and Helaomodaka were sown. 10 days after sowing, the hydrating powders of the compounds of the present invention and comparative compounds in Table 4 prepared according to Formulation Example 2 were diluted with water so that the amount of active ingredient of each compound became the prescribed amount in Table 4, and then dropped onto the water surface. Processed. After that, leave it in a greenhouse and process it.
Table 4 shows the results of evaluating the herbicidal effect using the efficacy index shown in Test Example 1 on the 20th day. The leaf age of each weed at the time of chemical treatment was 1-leaf stage for wild grass, Japanese cypress, and cypress, and 0.5 to 1 leaf stage for firefly and Helaomodaka.
It was in the leaf stage.
【表】【table】
【表】
以上の結果より、本発明化合物は比較化合物に
比べて除草効果が高く、作物に対しては極めて安
全であることがわかる。[Table] From the above results, it can be seen that the compounds of the present invention have a higher herbicidal effect than the comparative compounds and are extremely safe for crops.
Claims (1)
ル基を示し、R3は低級アルコキシ基または低級
アルキルチオ基を示し、Ｘはハロゲン原子を示
し、Ｙは酸素原子またはイオウ原子を示し、ｎは
１〜２の整数を示す。） にて表わされる２−ペンテン酸アミド誘導体。 ２ R1がブチル基である特許請求の範囲第１項
記載の２−ペンテン酸アミド誘導体。 ３ R2がメチル基、エチル基またはプロピル基
である特許請求の範囲第１項または第２項記載の
２−ペンテン酸アミド誘導体。 ４ R3がメトキシ基、エトキシ基、プロポキシ
基またはメチルチオ基である特許請求の範囲第１
項ないし第３項のいずれかに記載の２−ペンテン
酸アミド誘導体。 ５ Ｘが塩素原子である特許請求の範囲第１項な
いし第４項のいずれかに記載の２−ペンテン酸ア
ミド誘導体。 ６ 式 （式中、R1およびR2は炭素数１〜４の低級アルキ
ル基を示し、R3は低級アルコキシ基または低級
アルキルチオ基を示し、Ｘはハロゲン原子を示
し、Ｙは酸素原子またはイオウ原子を示し、ｎは
１〜２の整数を示す。） にて表わされる２−ペンテン酸アミド誘導体を有
効成分として含有する除草剤。 ７ R1がブチル基である特許請求の範囲第６項
記載の除草剤。 ８ R2がメチル基、エチル基またはプロピル基
である特許請求の範囲第６項または第７項記載の
除草剤。 ９ R3がメトキシ基、エトキシ基、プロポキシ
基またはメチルチオ基である特許請求の範囲第６
項ないし第８項のいずれかに記載の除草剤。 １０ Ｘが塩素原子である特許請求の範囲第６項
ないし第９項のいずれかに記載の除草剤。[Claims] 1 formula (In the formula, R 1 and R 2 represent a lower alkyl group having 1 to 4 carbon atoms, R 3 represents a lower alkoxy group or a lower alkylthio group, X represents a halogen atom, and Y represents an oxygen atom or a sulfur atom. and n represents an integer of 1 to 2.) A 2-pentenoic acid amide derivative represented by: 2. The 2-pentenoic acid amide derivative according to claim 1, wherein R 1 is a butyl group. 3. The 2 -pentenoic acid amide derivative according to claim 1 or 2, wherein R 2 is a methyl group, an ethyl group, or a propyl group. 4 Claim 1 in which R 3 is a methoxy group, ethoxy group, propoxy group or methylthio group
2-pentenoic acid amide derivative according to any one of items 1 to 3. 5. The 2-pentenoic acid amide derivative according to any one of claims 1 to 4, wherein X is a chlorine atom. 6 formula (In the formula, R 1 and R 2 represent a lower alkyl group having 1 to 4 carbon atoms, R 3 represents a lower alkoxy group or a lower alkylthio group, X represents a halogen atom, and Y represents an oxygen atom or a sulfur atom. and n is an integer of 1 to 2.) A herbicide containing a 2-pentenoic acid amide derivative represented by the following as an active ingredient. 7. The herbicide according to claim 6, wherein R 1 is a butyl group. 8. The herbicide according to claim 6 or 7, wherein R 2 is a methyl group, ethyl group, or propyl group. 9 Claim 6 in which R 3 is a methoxy group, ethoxy group, propoxy group or methylthio group
The herbicide according to any one of Items 8 to 8. 10 The herbicide according to any one of claims 6 to 9, wherein X is a chlorine atom.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10793285A JPS60260587A (en) | 1985-05-20 | 1985-05-20 | 2-pentenoic acid amide derivative and herbicide containing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10793285A JPS60260587A (en) | 1985-05-20 | 1985-05-20 | 2-pentenoic acid amide derivative and herbicide containing same |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11396880A Division JPS5738757A (en) | 1980-08-21 | 1980-08-21 | 2-pentenamide derivative and germicide and herbicide containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60260587A JPS60260587A (en) | 1985-12-23 |
| JPS6260389B2 true JPS6260389B2 (en) | 1987-12-16 |
Family
ID=14471711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10793285A Granted JPS60260587A (en) | 1985-05-20 | 1985-05-20 | 2-pentenoic acid amide derivative and herbicide containing same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60260587A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0672094A (en) * | 1992-08-27 | 1994-03-15 | Teijin Ltd | Sheet for white board |
-
1985
- 1985-05-20 JP JP10793285A patent/JPS60260587A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0672094A (en) * | 1992-08-27 | 1994-03-15 | Teijin Ltd | Sheet for white board |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60260587A (en) | 1985-12-23 |
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