JPS5998004A - Herbicide containing 1,2,4-triazole derivative - Google Patents
Herbicide containing 1,2,4-triazole derivativeInfo
- Publication number
- JPS5998004A JPS5998004A JP20648682A JP20648682A JPS5998004A JP S5998004 A JPS5998004 A JP S5998004A JP 20648682 A JP20648682 A JP 20648682A JP 20648682 A JP20648682 A JP 20648682A JP S5998004 A JPS5998004 A JP S5998004A
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- group
- compound number
- herbicide
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Abstract
Description
【発明の詳細な説明】
本発明は一般式（Ｉ）
（式中、Ｒ，、Ｒ，は水素原子、アルキル基、ハロゲン
原子又はハロゲノアルキル基を表わし、Ｒ１は水素原子
、ハロゲン原子又はアルキル基を表わし、Ｒ４はシアノ
基、アミ ド基、チオアミド基、Ｎ−アルキルアミド基
、Ｎ−ハロゲノアルキルアミド基、Ｎ−メトキシアルキ
ルアミＦ基、Ｎ−アルケニルアミド基、Ｎ−ハロゲノア
ルケニルアミド基、Ｎ−アシルアミド基、Ｎ−ハロゲノ
アシルアミド基又はＮ−メチルチオカルバモイルアミド
基を表わす）で示されるＬ Ｌ ４−トリアゾール誘導
体を有効成分とする除草剤に関する。Detailed Description of the Invention The present invention is based on the general formula (I) (wherein R, R, represents a hydrogen atom, an alkyl group, a halogen atom, or a halogenoalkyl group, and R1 represents a hydrogen atom, a halogen atom, or an alkyl group). R4 represents a cyano group, an amide group, a thioamide group, an N-alkylamide group, an N-halogenoalkylamide group, an N-methoxyalkylamide F group, an N-alkenylamide group, an N-halogenoalkenylamide group, and an N-alkenylamide group. - acylamido group, N-halogenoacylamido group or N-methylthiocarbamoylamide group) as an active ingredient.
本発明者らは、種々研究を積み重ねた結果、上記一般式
（Ｉ）で表わされる１、 ２．４−）！Ｊアゾール誘導
体が優れた実用的除草効果を有する事を発見し、本発明
に至った。As a result of various studies, the present inventors have found that 1, 2.4-) represented by the above general formula (I)! It was discovered that J azole derivatives have excellent practical herbicidal effects, leading to the present invention.
本発明の一般式（Ｉ）の化合物（以下、本発明化合物と
略称する）はイネ、コムギ、トウモロコシ等に薬害を生
ずる事なく、種子発芽試験、土壌処理試験、茎葉散布処
理試験等の除草試験において広葉およびイネ科植物に除
草活性を示し、特に広葉植物（スベリヒュ、シ四ス、ハ
コベ、タネッケパナ等）には優れた除草活性番有する事
を発見した。The compound of general formula (I) of the present invention (hereinafter abbreviated as the compound of the present invention) does not cause phytotoxicity to rice, wheat, corn, etc., and has been tested in herbicidal tests such as seed germination tests, soil treatment tests, and foliar spray treatment tests. It has been found that it exhibits herbicidal activity against broad-leaved plants and gramineous plants, and has particularly excellent herbicidal activity against broad-leaved plants (purslane, shishiso, chickweed, ash, etc.).
その除草剤としての施用範囲は、水田、畑地、果樹園等
の農耕地の他、花卉栽培への使用があげられる。The scope of its application as a herbicide includes use in agricultural land such as paddy fields, fields, and orchards, as well as floriculture.
本発明化合一は、下記の反応式のいずれかによって合成
゛され得る。The compound of the present invention can be synthesized by any of the following reaction formulas.
１）一般式（Ｉ）中のＲ１がアミド基、Ｎ−アルキルア
ミド基、Ｎ−ノ叩デノアルキルアミド基、Ｎ−メトキー
ジアルキルアミド基、Ｎ−アルケニルアミド基又はＮ−
ハロゲノアルケニルアミド基の場合：
反応式１−
（１）
反応式１に示されるように、４−フェニルヒＦラゾノー
２−フェニルオキサゾリン−５−オン誘導体（ＩＩ）を
アセトン中で適当なアミン誘導体Ｉヒ反応させ、次いで
、塩酸を用いて環化させる事によシ、簡便に合成する事
ができる。1) R1 in general formula (I) is an amide group, an N-alkylamide group, an N-denoalkylamide group, an N-methoxydialkylamide group, an N-alkenylamide group, or an N-
In the case of halogenoalkenylamide group: Reaction formula 1- (1) As shown in Reaction formula 1, 4-phenylhyFlazono-2-phenyloxazolin-5-one derivative (II) is mixed with a suitable amine derivative I in acetone. It can be easily synthesized by reacting and then cyclizing using hydrochloric acid.
２）一般式（Ｉ）中のＲ４がＮ−アシルアミド基又はＮ
−ハロゲノアシルアミド基を示す場合：
反応式 ２
（）
反応式２で表わされるように、１．２．４−） リアゾ
ール誘導体（ＩＶ）をベンゼンやトルエンなどの不活性
溶媒中で酸塩化物あるいは酸無水物でアシル化する事に
よシ、容易に合成する事ができる。2) R4 in general formula (I) is an N-acylamido group or N
- In the case of a halogenoacylamide group: Reaction formula 2 () As shown in reaction formula 2, 1.2.4-) The lyazole derivative (IV) is converted into an acid chloride or an acid chloride in an inert solvent such as benzene or toluene. It can be easily synthesized by acylation with an acid anhydride.
３）一般式（Ｉ）中のＲ４がシアン基の場合：反応式
３
（）
反応式３で表わされるように、１．２．４−）リアゾー
ル誘導体（■）をベンゼンやトルエンなどの溶媒中でチ
オニルクロライドと反応させる事によって合成できる。3) When R4 in general formula (I) is a cyan group: Reaction formula
3 () As shown in Reaction Formula 3, the 1.2.4-) lyazole derivative (■) can be synthesized by reacting it with thionyl chloride in a solvent such as benzene or toluene.
４）一般式（Ｉ）中Ｒ４がチオアミド基の場合：反応式
４
反応式４で表わされるように、Ｌ２１４−）リアゾール
誘導体（７）をアンモニアを吸収させたメタノール中で
硫化水素と反応させる事によって合成できる。4) When R4 in general formula (I) is a thioamide group: Reaction formula 4 As shown in Reaction formula 4, the L214-) lyazole derivative (7) is reacted with hydrogen sulfide in methanol that has absorbed ammonia. It can be synthesized by
５）一般式（Ｉ）中Ｒ６がＮ−メチルチオカルバモイル
アミド基の場合：
反応式 ５
反応式５で表わされるように、１，２．４−）リアゾー
ル誘導体（ＶＩ）をベンゼンやトルエンなどの溶媒中で
、Ｎ−メチルチオ尿素と反応させる事によって合成でき
る。5) When R6 in general formula (I) is an N-methylthiocarbamoylamide group: Reaction formula 5 As shown in Reaction formula 5, the 1,2.4-)lyazole derivative (VI) is dissolved in a solvent such as benzene or toluene. Among them, it can be synthesized by reacting with N-methylthiourea.
本発明化合物の具体例とその理化学的性質を下記第１表
に示す。Specific examples of the compounds of the present invention and their physical and chemical properties are shown in Table 1 below.
次に本発明化合物の合成例を以下に示す。Next, a synthesis example of the compound of the present invention is shown below.
化合物の番号は第１表に示した番号に対応する。The compound numbers correspond to the numbers shown in Table 1.
１−（３−メチルフェニル）−３−シアノ−５−フェニ
ル−１，２，４−）リアゾール ５．２ Ｐｃ ０．０
２モル）をアンモニアガスを吸収させたメタノール１０
〇−に溶解させ、４０〜５０℃下でＨ，Ｓガスを２０分
間吹き込み反応させた。この反応液を減圧濃縮し、これ
をヘキサン−アセトン混合溶媒で洗浄後、トルエン−ヘ
キサン（３０ｍｇ−Ｉ Ｍ）で再結１１’＆Ｌ。1-(3-methylphenyl)-3-cyano-5-phenyl-1,2,4-)riazole 5.2 Pc 0.0
10 methanol with ammonia gas absorbed (2 mol)
It was dissolved in 〇- and reacted by blowing H and S gases at 40 to 50°C for 20 minutes. The reaction solution was concentrated under reduced pressure, washed with a hexane-acetone mixed solvent, and then reconcentrated with toluene-hexane (30 mg-IM).
て、１．３？の淡黄色の結晶を得た。融点１５４〜６℃
、収率２２％
１−（３−（３，３，３−）リフ四ルプ四ピル）フェニ
ルシー５−フェニル−１，２，４−）リアゾール−３−
カルボキサミＩ−”３．６ Ｆ （０，０１モル）を無
水酢酸３〇−中で２時間還流反応した。この反応液を減
圧濃縮し、これをトルエン−ヘキサン（３０ｍ−１０ｆ
ｎｔ）で再結晶しマ、３．０？の無色の結晶を得た。融
点１４゜１５０℃、収率７５％
１−７二二／Ｉ／−５−（３−メチルフェニル） −１
，２，４−トリアゾール−３−カルボキサミド、２．８
１ｉ’ （０，０１モル）をトルエン５０ゴに採り、
）リクロルアセチルクロ２イド２．２ Ｆ（０，０１
２モル）を加えて３時間還流反応させた。この反応液を
減圧濃縮し、これをトルエン−ヘキサン（３む−−１０
−）で再結晶して、３．０？の無色の結晶を得た。融点
１３０〜１３２℃、収率７２チ
１−（３−メチルフェニル）−５−フェニル−１，２，
４−トリアゾール−３−カルボキシリックアミドクロリ
ド３．０ｙ（ｏ、ｏｉモル）をトルエン５０−に採シ、
Ｎ−メチルチオ尿素０．９ Ｆ （０，０１モル）を加
え１時間還流反応させたつこの反応液を減圧濃縮し、こ
れをアセトンで洗浄後、トルエンで再結晶して１．８ｙ
−の無色の結晶を得た。融点１８５〜１８７℃、収率５
２チ
４−ンエニルヒドラゾノ−２−（３−メチルフェニルオ
キサゾリン）−５７オン２．８５１’ （０，０１モル
）をアセトン３０ｍ１に懸濁させ、４０ｑ６メチルアミ
ン水を１．０１ｉ’（０，０１３１＝＃）加え、１０分
間還流し、冷却後、濃塩酸を１．５−滴下し、５分間還
流した。Wait, 1.3? A pale yellow crystal of was obtained. Melting point 154~6℃
, yield 22% 1-(3-(3,3,3-)rif4rp4pyr)phenylcy5-phenyl-1,2,4-)riazole-3-
Carboxami I-"3.6F (0.01 mol) was refluxed in acetic anhydride 30-30-2 hours for 2 hours. The reaction solution was concentrated under reduced pressure, and then mixed with toluene-hexane (30m-10f).
nt) recrystallized with 3.0? Colorless crystals were obtained. Melting point: 14° to 150°C, yield: 75% 1-722/I/-5-(3-methylphenyl)-1
, 2,4-triazole-3-carboxamide, 2.8
1i' (0.01 mol) was added to 50 g of toluene,
) Lichloracetyl chloride 2.2 F(0,01
2 mol) was added thereto and the mixture was refluxed for 3 hours. The reaction solution was concentrated under reduced pressure and mixed with toluene-hexane (3 mm - 10 mm).
-) and recrystallize with 3.0? Colorless crystals were obtained. Melting point: 130-132°C, yield: 72 1-(3-methylphenyl)-5-phenyl-1,2,
3.0 y (o, oi mol) of 4-triazole-3-carboxylic amide chloride was taken into 50 mol of toluene,
After adding 0.9 F (0.01 mol) of N-methylthiourea and refluxing for 1 hour, the reaction solution was concentrated under reduced pressure, washed with acetone, and recrystallized with toluene to give 1.8 y.
- colorless crystals were obtained. Melting point 185-187℃, yield 5
2.851' (0.01 mol) of 2th-enylhydrazono-2-(3-methylphenyloxazoline)-57one was suspended in 30 ml of acetone, and 40q6 methylamine water was suspended in 1.01 i' (0 ,0131=#) and refluxed for 10 minutes. After cooling, 1.5 drops of concentrated hydrochloric acid were added, and the mixture was refluxed for 5 minutes.
冷却後、反応液を３００７！の水中に投じ析出物を戸取
し、これをエタノール−水（１０ｆｆ１７！−２ｍ）で
再結晶して１．７Ｆ！−の淡黄色の結晶を得た。融点１
４９〜１５０℃、収率５９ｑ６
１−（３−メチルフェニル）−５−フェニル−１，２，
４−トリアゾール−３−カルボキサ−ミド２．８ ｆ！
（０，０１モル）をトルエン５０−に採り、チオニルク
ロジイドを１．６Ｐ（０，０１３モル）を加え３時間還
流反応させたこの反応液を減圧濃縮し、少量のエタノー
ルで洗浄後、エタノールで再結晶して１．４ｙ−の無色
の結晶を得た。融点９０〜９１℃、収率５４チ・次に実
施例の若干をあげ、るが、担体（稀釈剤）及び助剤、そ
の混合比及び有効成分は広い範囲で変更し得るものであ
る。After cooling, the reaction solution was mixed with 3007! The precipitate was collected and recrystallized with ethanol-water (10ff17!-2m) to 1.7F! - pale yellow crystals were obtained. Melting point 1
49-150°C, yield 59q6 1-(3-methylphenyl)-5-phenyl-1,2,
4-triazole-3-carboxamide 2.8 f!
(0.01 mol) was taken in 50-mol of toluene, 1.6P (0.013 mol) of thionyl clodide was added, and the reaction mixture was refluxed for 3 hours. The reaction solution was concentrated under reduced pressure, washed with a small amount of ethanol, and then washed with ethanol. Recrystallization was carried out to obtain 1.4y-colorless crystals. Melting point: 90-91 DEG C. Yield: 54 cm.Next, some examples will be given, but the carrier (diluent) and auxiliary agents, their mixing ratio and the active ingredients can be varied within a wide range.
化合物層３５０部
リグニンスルホン酸塩 ５部アルキルス
ルホン酸塩 ３部 珪 藻 ±
４２部を混合粉砕して水利剤とし、水で稀釈
して使用した。Compound layer 350 parts Lignosulfonate 5 parts Alkyl sulfonate 3 parts Diatom ±
42 parts were mixed and pulverized to make an irrigation agent, which was diluted with water and used.
化合物Ｅ、１０２５部
キ シ し ン ６５部ポリ
オキシエチレンアルキルアリルニーカル １０部を均一
混合して乳剤とし水で稀釈して使用した。Compound E, 1025 parts xylene 65 parts polyoxyethylene alkylaryl nical 10 parts were uniformly mixed to form an emulsion, which was diluted with water and used.
実施例３：粒剤
化合物層１２８部
ベントナイト ４０部
り し − ４５部リグ
ニンスルホン酸塩 ７部を均一に混合
、更に水を加え練合せ、押出式超粒機で粒状に加工後、
乾燥して粒剤とした。Example 3: Granule compound layer 128 parts Bentonite 40 parts Rishi - 45 parts Lignosulfonate 7 parts were mixed uniformly, further water was added and kneaded, and after processing into granules with an extrusion type supergranulator,
It was dried and made into granules.
次に本発明化合物の有効性を証するため若干の試験例を
示す。Next, some test examples will be shown to demonstrate the effectiveness of the compounds of the present invention.
プランタ−（６５０Ｘ２１０Ｘ２００訓）に土壌をつめ
畑地状とし、試験活物の種子の一定量を播種し覆土した
後、本発明化合物が、アールｆｉ 、り ５０ Ｓ’−
相当量になるように調整した稀釈液を土壌表面に均一に
散布し、温室内にて育生管理した。処理２５日後に次の
基準にて評価した。Fill a planter (650 x 210 x 200) with soil to make it into a field, sow a certain amount of seeds of the test live species, and cover with soil.
A diluted solution adjusted to a considerable amount was uniformly spread over the soil surface, and growth was managed in a greenhouse. After 25 days of treatment, evaluation was made based on the following criteria.
評価基準 ０ 殺草効果なし １ ２０％の殺草効果 ２ ４０％ 〃 ３ ６０チ １ ４ ８０％ 〃 ５１ｏＯ％ Ｉ 上記試験の結果を第２表に示す。Evaluation criteria 0 No weed killing effect 1. 20% weed killing effect 2 40% 3 60chi 1 4 80% 51oO% I The results of the above test are shown in Table 2.
試験例２：植物発生始期処理の除草効果試験試験例１と
同様操作により播種し、植物力４ｉ〜２葉期に達したと
きに、有効成分アール邑シ５゜ｉ相当量の水懸濁液を茎
葉部土壌表面に均一に散布し、温室内にて育生管理した
。処理２５日後に試験例１と同様に調査した。Test Example 2: Testing the herbicidal effect of treatment at the beginning of plant development The seeds were sown in the same manner as in Test Example 1, and when the plant power reached 4i to 2 leaf stage, an aqueous suspension containing the active ingredient Earle in an amount equivalent to 5゜i was applied. was evenly spread on the soil surface of the stems and leaves, and the growth was managed in a greenhouse. The same investigation as in Test Example 1 was conducted 25 days after the treatment.
上記試験の結果を第３表に示す。The results of the above test are shown in Table 3.
第１図は化合物番号１、第２図は化合物番号２、第３図
は化合物番号３、第４図は化合物番号４、第５図は化合
物番号５、第６図は化合物番号６、第７図は化合物番号
７、第８図は化合物番号８、第９図は化合物番号９、第
１０図は化合物番号１０、第１１図は化合物番号１１、
第１２図は化合物番号１２、第１３図は化合物番号１３
、第１４図は化合物番号１４、第１５図は化合物番号１
５、第１６図は化合物番号１６、第１７図は化合物番号
１７、第１８図は化合物番号１８、第１９図は化合物番
号１９、第２０図は化合物番号２０．第２１図は化合物
番号２１、第２２図は化合物番号２２、第２３図は化合
物番号２３、第２−４図は化合物番号２４、第２５図は
化合物番号２５、第２６図は化合物番号２６、第２７図
は化合物番号２７、第２８図は化合物番号２８、第２９
図は化合物番号２９、第３０図は化合物番号３０、第３
１図は化合物番号３１、第３２図は化合物番号３２、第
３３図は化合物番号３３、第３４図線化合物番号３４の
赤外吸収スペクトルを示す図である。
、代理人ＩＩ士今 村 元Figure 1 shows compound number 1, Figure 2 shows compound number 2, Figure 3 shows compound number 3, Figure 4 shows compound number 4, Figure 5 shows compound number 5, Figure 6 shows compound number 6, and number 7. The figure shows compound number 7, figure 8 shows compound number 8, figure 9 shows compound number 9, figure 10 shows compound number 10, figure 11 shows compound number 11,
Figure 12 shows compound number 12, Figure 13 shows compound number 13.
, Figure 14 shows compound number 14, Figure 15 shows compound number 1.
5, Figure 16 shows compound number 16, Figure 17 shows compound number 17, Figure 18 shows compound number 18, Figure 19 shows compound number 19, and Figure 20 shows compound number 20. Figure 21 shows compound number 21, Figure 22 shows compound number 22, Figure 23 shows compound number 23, Figures 2-4 show compound number 24, Figure 25 shows compound number 25, Figure 26 shows compound number 26, Figure 27 shows compound number 27, Figure 28 shows compound number 28 and 29.
The figure shows compound number 29, and the figure 30 shows compound number 30.
Figure 1 shows the infrared absorption spectra of Compound No. 31, Figure 32 shows Compound No. 32, Figure 33 shows Compound No. 33, and Figure 34 shows the infrared absorption spectra of Compound No. 34. , Moto Imamura, Agent II
Claims (1)
原子又はハロゲノアルキル基を表わし、Ｒ８は水素原子
、ハロゲン原子又はアルキル基を表わし、Ｒ４はシアノ
基、アミド基、チオアミド基、Ｎ−アルキルアミド基、
Ｎ−ハロゲノアルキルアミド基、Ｎ−メトキシアルキル
アミド基、Ｎ−アルケニルアミド基、Ｎ−ハロゲノアル
ケニルアミド基、Ｎ−アシルアミド基、Ｎ−ハロ２ノア
クルアミド基又はＮ−メチルチオカルバモイルアミド基
を表わす）を有する１、 ２．４−）リアゾール誘導体
を含有する除草剤。[Claims] General formula (I) (wherein R,, R1 represents a hydrogen atom, an alkyl group, a halogen atom, or a halogenoalkyl group, R8 represents a hydrogen atom, a halogen atom, or an alkyl group, and R4 represents a hydrogen atom, a halogen atom, or an alkyl group; cyano group, amide group, thioamide group, N-alkylamide group,
N-halogenoalkylamide group, N-methoxyalkylamide group, N-alkenylamide group, N-halogenoalkenylamide group, N-acylamide group, N-halo2noacrylamide group or N-methylthiocarbamoylamide group). 1, 2.4-) A herbicide containing a lyazole derivative.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20648682A JPS5998004A (en) | 1982-11-25 | 1982-11-25 | Herbicide containing 1,2,4-triazole derivative |
| DE3316300A DE3316300A1 (en) | 1982-05-07 | 1983-05-04 | HERIBICIDAL COMPOSITION CONTAINING A DERIVATIVE OF 1,2,4-TRIAZOLE AS AN ACTIVE SUBSTANCE |
| GB08312422A GB2120665B (en) | 1982-05-07 | 1983-05-06 | 1,2,4-triazole derivatives useful as herbicides |
| FR8307622A FR2526271B1 (en) | 1982-05-07 | 1983-05-06 | HERBICIDE COMPOSITION CONTAINING 1, 2, 4-TRIAZOLE DERIVATIVE AS ACTIVE INGREDIENT |
| US06/858,531 US4795484A (en) | 1982-05-07 | 1986-04-24 | Herbicidal composition containing a derivative of 1,2,4-triazole as an active ingredient |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20648682A JPS5998004A (en) | 1982-11-25 | 1982-11-25 | Herbicide containing 1,2,4-triazole derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5998004A true JPS5998004A (en) | 1984-06-06 |
| JPH0360824B2 JPH0360824B2 (en) | 1991-09-17 |
Family
ID=16524166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20648682A Granted JPS5998004A (en) | 1982-05-07 | 1982-11-25 | Herbicide containing 1,2,4-triazole derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5998004A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63152366A (en) * | 1985-10-25 | 1988-06-24 | Kureha Chem Ind Co Ltd | 1,2,4-triazole-3-carboxyamide, production and utilization thereof as herbicide |
| US5094684A (en) * | 1987-06-08 | 1992-03-10 | Kureha Kagaku Kogyo Kabushiki Kaisha | Derivative of 1,5-diphenyl-1h-1,2-triazole-3-carboxamide, herbicidal compositions containing the derivative and process for producing the derivative |
| US5646291A (en) * | 1990-12-27 | 1997-07-08 | Kureha Chemical Industry Co., Ltd. | Process for the manufacture of 2-phenyl-4,5-oxazoledione 4-phenylhydrazone derivatives |
| WO2008096675A1 (en) * | 2007-02-06 | 2008-08-14 | Nippon Soda Co., Ltd. | Broad-leaved perennial weed control agent for grass, and method for control of broad-leaved perennial weed in grass |
| US7612105B2 (en) | 1998-04-27 | 2009-11-03 | Kumiai Chemical Industry Co., Ltd. | 3-arylphenyl sulfide derivative and insecticide and miticide |
| JP2019534848A (en) * | 2016-10-12 | 2019-12-05 | アールティーアイ インターナショナル | Heterocyclic apelin receptor (APJ) agonists and their use |
| US11401244B2 (en) | 2014-06-06 | 2022-08-02 | Research Triangle Institute | Apelin receptor (APJ) agonists and uses thereof |
| US11535630B2 (en) | 2015-12-09 | 2022-12-27 | Research Triangle Institute | Apelin receptor (APJ) agonists and uses thereof |
-
1982
- 1982-11-25 JP JP20648682A patent/JPS5998004A/en active Granted
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63152366A (en) * | 1985-10-25 | 1988-06-24 | Kureha Chem Ind Co Ltd | 1,2,4-triazole-3-carboxyamide, production and utilization thereof as herbicide |
| JPH0529224B2 (en) * | 1985-10-25 | 1993-04-28 | Kureha Chemical Ind Co Ltd | |
| US5094684A (en) * | 1987-06-08 | 1992-03-10 | Kureha Kagaku Kogyo Kabushiki Kaisha | Derivative of 1,5-diphenyl-1h-1,2-triazole-3-carboxamide, herbicidal compositions containing the derivative and process for producing the derivative |
| US5646291A (en) * | 1990-12-27 | 1997-07-08 | Kureha Chemical Industry Co., Ltd. | Process for the manufacture of 2-phenyl-4,5-oxazoledione 4-phenylhydrazone derivatives |
| US7767626B2 (en) | 1998-04-27 | 2010-08-03 | Kumiai Chemical Industry Co., Ltd. | 3-arylphenyl sulfide derivative and insecticide and miticide |
| US7612105B2 (en) | 1998-04-27 | 2009-11-03 | Kumiai Chemical Industry Co., Ltd. | 3-arylphenyl sulfide derivative and insecticide and miticide |
| JPWO2008096675A1 (en) * | 2007-02-06 | 2010-05-20 | 日本曹達株式会社 | Lawn broadleaf perennial weed control agent and lawn broadleaf perennial weed control method |
| WO2008096675A1 (en) * | 2007-02-06 | 2008-08-14 | Nippon Soda Co., Ltd. | Broad-leaved perennial weed control agent for grass, and method for control of broad-leaved perennial weed in grass |
| KR101041755B1 (en) | 2007-02-06 | 2011-06-17 | 닛뽕소다 가부시키가이샤 | Broadleaf perennial weed control agent for grass, and method for controlling broadleaf perennial weeds in grass |
| US11401244B2 (en) | 2014-06-06 | 2022-08-02 | Research Triangle Institute | Apelin receptor (APJ) agonists and uses thereof |
| US11535630B2 (en) | 2015-12-09 | 2022-12-27 | Research Triangle Institute | Apelin receptor (APJ) agonists and uses thereof |
| USRE49594E1 (en) | 2015-12-09 | 2023-08-01 | Research Triangle Institute | Apelin receptor (APJ) agonists and uses thereof |
| JP2019534848A (en) * | 2016-10-12 | 2019-12-05 | アールティーアイ インターナショナル | Heterocyclic apelin receptor (APJ) agonists and their use |
| US11926612B2 (en) | 2016-10-12 | 2024-03-12 | Research Triangle Institute | Heterocyclic apelin receptor (APJ) agonists and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0360824B2 (en) | 1991-09-17 |
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