JPS58194866A - Triazole derivative and herbicide containing the same - Google Patents
Triazole derivative and herbicide containing the sameInfo
- Publication number
- JPS58194866A JPS58194866A JP7701082A JP7701082A JPS58194866A JP S58194866 A JPS58194866 A JP S58194866A JP 7701082 A JP7701082 A JP 7701082A JP 7701082 A JP7701082 A JP 7701082A JP S58194866 A JPS58194866 A JP S58194866A
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- JP
- Japan
- Prior art keywords
- group
- formula
- compound number
- methoxyacetyl
- acetyl
- 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.)
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- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、一般式(1)
(式中、■、は水素原子、アルキル基又はヒドロキシア
ルキル基金表わし、R2は水素原子、アルキル基、ハロ
ゲノアルキル基、ヒドロキシアルキル基。DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula (1) (wherein ■ represents a hydrogen atom, an alkyl group, or a hydroxyalkyl group, and R2 represents a hydrogen atom, an alkyl group, a halogenoalkyl group, or a hydroxyalkyl group).
シアノアルキル基、アセチル基、ハロゲノアセチル基、
メトキシアセチル基、アミン基、メトキシ基又は水酸基
を表わし、R3、’it、 ’lまそれぞれ水素原子、
アルキル基又はハロゲン原子を表わす)で示される新規
な1,2.4−1Jアゾ一ル誘導体及びこれ全有効成分
とする除草剤に関する。cyanoalkyl group, acetyl group, halogenoacetyl group,
Represents a methoxyacetyl group, amine group, methoxy group or hydroxyl group, R3, 'it, 'l each represent a hydrogen atom,
The present invention relates to a novel 1,2,4-1J azoyl derivative represented by an alkyl group or a halogen atom, and a herbicide containing the same as an active ingredient.
本発明者らは、種々研究♀積み重ねた結果、上記一般式
(りで表わされる1、2.4−トIJアゾール誘導体が
優れた実用的除草効果金屑すること全発見し本発明に至
った。As a result of various researches, the present inventors have discovered that the 1,2,4-to-IJ azole derivative represented by the above general formula (R) has an excellent practical herbicidal effect, leading to the present invention. .
本発明の一般式(1)の化合物(以下、本発明化合物と
略称する)はイネ、小麦、トウモロコア等に薬害を生ず
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(スベリヒエ、シロザ、ハ
コベ、タネッケバナ等)には侵れた除草活性を有するこ
とを発見した。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めげ
られる。The compound of general formula (1) of the present invention (hereinafter referred to as the compound of the present invention) does not cause any chemical damage to rice, wheat, corn core, etc., and has been tested in herbicidal tests such as seed germination tests, soil treatment tests, and foliar spray treatment tests. It was discovered that it exhibited herbicidal activity against broad-leaved plants and gramineous plants, and in particular, it had a herbicidal activity that was ineffective against broad-leaved plants (purslane, whitewort, chickweed, aspergillus, etc.). Its application range as a herbicide is paddy fields,
In addition to agricultural land such as fields and orchards, use for floriculture is discouraged.
本発明化合物は、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(り中のR1がアセチル基、ハロゲノアセチ
ル基、メトキシアセチル基以外の置換基を示す場合:
反応式1に示されるように、4−フェニルヒドラゾノ−
2−フェニルオキサゾリン−5−誘導体(II)にアセ
トン又はジオキサン中で適当なアミン誘導体(1) ”
を反応させ、次いで塩酸を用いて環化させることにより
、簡便に合成することができる。1) General formula (when R1 in the formula represents a substituent other than an acetyl group, a halogenoacetyl group, or a methoxyacetyl group: As shown in reaction formula 1, 4-phenylhydrazono-
2-phenyloxazoline-5-derivative (II) in acetone or dioxane with a suitable amine derivative (1)
It can be easily synthesized by reacting and then cyclizing using hydrochloric acid.
2)一般式0)中のR,がアセチル基、ハロゲノアセチ
ル基、メトキシアセチル基金示す場合:反応式2で表わ
されるように1.2.4−)リアゾール訪導体(■)
’に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ことにより容易に合成
することができる。2) When R in general formula 0) represents an acetyl group, a halogenoacetyl group, or a methoxyacetyl group: 1.2.4-) Riazole visiting conductor (■) as shown in reaction formula 2
' can be easily synthesized by acylating with acid chloride or acid anhydride in an inert solvent such as benzene or toluene.
第1表に示す。Shown in Table 1.
−8−
次に本発明化合物の合成側全以下に示す。化合物の番号
は表1に示した番号に対応する。-8- Next, the entire synthesis of the compound of the present invention is shown below. Compound numbers correspond to those shown in Table 1.
合成例1z化合物番号2の合成
4−()−、チルフェニルヒドラゾノ)−2−フェニル
オキサゾリン−5−オン(式nにおいて、R5が水素原
子R64が3位メチル基會表わす)2.8f (0,0
1モル)をアセトン30m1に懸濁させ、室温下にて4
0%メチルアミン水1.Of (0,013モル)力0
えて30分間還流を行ない、冷却後、濃4酸を1.5−
滴下する。滴下後、再び5分間還流する。Synthesis Example 1z Synthesis of Compound No. 2 4-()-, tylphenylhydrazono)-2-phenyloxazolin-5-one (In formula n, R5 is a hydrogen atom R64 represents a methyl group at the 3-position) 2.8f ( 0,0
1 mol) was suspended in 30 ml of acetone, and 4
0% methylamine water 1. Of (0,013 moles) force 0
reflux for 30 minutes, and after cooling, convert the concentrated 4-acid into 1.5-
Drip. After dropping, the mixture is refluxed again for 5 minutes.
冷却後、反応i’i 300−の水中に投じ、析出物を
ni*、これ全エタノール−水(10m−2yd)で再
結晶すると1.81の無色の結晶が得られる。融点13
5〜6℃、収率61.7%。After cooling, the precipitate was poured into water of reaction i'i 300-, and the precipitate was recrystallized from ni*, total ethanol-water (10 m-2yd) to obtain colorless crystals of 1.81. Melting point 13
5-6°C, yield 61.7%.
合成例2z化合物番号3の合成
4−(3−メチルフェニルヒドラゾノ)−2−フェニル
オキサゾリン−5−オン(式■において、R1,が水素
原子、R14が3位メチル基を表わす)2.8 r (
0,01モル)會ジオキサン30m1に加え、アニリ7
1.3r(0,013モル)加えて、4時間還流する。Synthesis Example 2z Synthesis of Compound No. 3 4-(3-methylphenylhydrazono)-2-phenyloxazolin-5-one (In the formula (■), R1 represents a hydrogen atom and R14 represents a methyl group at the 3-position) 2.8 r (
0.01 mol) in addition to 30 ml of dioxane, Anili 7
Add 1.3r (0,013 mol) and reflux for 4 hours.
冷却後、濃塩酸を1.5−滴下して40℃で5分間加温
し冷却後、反応液を水50m1中に投じ、析出物を濾取
、これ全エタノール−ジオキサン(40ml −20m
l )で再結晶すると2.42の淡黄色の結晶が得られ
る。融点204〜61Q収率66.7%合成例3:化合
物番号7の合成
4−(3−メチルフェニルヒドラゾノ)’−2−フェニ
ルオキサゾリン−5−オン(式■において、R8が水素
原子+R4が3位メチル基を表わす)2.8f(0,0
1モル)をジオキサン20−に加え、室温でヒドロキシ
アミン塩酸塩0.9 y (o、ot3モル)加える。After cooling, 1.5-ml of concentrated hydrochloric acid was added dropwise and heated at 40°C for 5 minutes. After cooling, the reaction solution was poured into 50 ml of water, the precipitate was collected by filtration, and the precipitate was dissolved in ethanol-dioxane (40 ml-20 ml).
Recrystallization with l) gives pale yellow crystals of 2.42. Melting point: 204-61Q Yield: 66.7% Synthesis Example 3: Synthesis of Compound No. 7 4-(3-Methylphenylhydrazono)'-2-phenyloxazolin-5-one (In formula 2, R8 is a hydrogen atom + R4 is 3-position methyl group) 2.8f (0,0
1 mol) in dioxane 20- and at room temperature 0.9 y (o,ot3 mol) of hydroxyamine hydrochloride are added.
次にカセイソーダ0,5 y (0,013モル)?溶
かした水溶液3 tnl Q滴下する。滴下後、40℃
に、30分間加温する。冷却後、濃塩酸1.5−全滴下
する。その佼、再び40℃に5分間、加縣■7、冷却す
る。反応Q 7z 200 mlの水中に投じ、析出物
を濾取、これ全アセトン−水で洗浄すると、1.92の
淡褐色結晶が得られる。融点155−8℃、収率64.
6%
曾成例4:化合物番号26の合成
1−(3−メ+ルフェニル)−5−フェニル−1,2,
4−)リアゾール−3−カルボキサミド(式■において
、R2とR8は水素原子、1t4は3位メチル基を表わ
す) 2.89 (0,01モル)をトルエン50v!
に爪u蜀させ、トリクロロアセチルクロライド2.29
(0,012モル)全加えて2時間還流する。Next, 0.5 y (0,013 mol) of caustic soda? Add 3 tnl Q of the dissolved aqueous solution dropwise. After dropping, 40℃
Heat for 30 minutes. After cooling, 1.5 g of concentrated hydrochloric acid is added dropwise. The container was cooled again to 40°C for 5 minutes. Reaction Q 7z was poured into 200 ml of water, and the precipitate was collected by filtration and washed with acetone-water to obtain light brown crystals of 1.92. Melting point: 155-8°C, yield: 64.
6% Synthesis Example 4: Synthesis of Compound No. 26 1-(3-Me+ruphenyl)-5-phenyl-1,2,
4-) Riazole-3-carboxamide (in the formula (2), R2 and R8 represent hydrogen atoms, and 1t4 represents a methyl group at the 3-position) 2.89 (0.01 mol) was dissolved in 50v of toluene!
Trichloroacetyl chloride 2.29
(0,012 mol) was added in total and refluxed for 2 hours.
反応混合物km縮し少量のエタノールで洗浄すると、2
,5vの無色結晶が得られる。融点161−2℃、収率
59.0%
1−(3−メf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(式■において
、R2とR3は水素原子、1t、は3位メチル基を衣わ
す) 2.8 f (0,01モル)(i7トルエン5
0m1に懸濁させ、メトキシアセチルクロライド1.3
y (0,012モル)を加えて2時間還流する。The reaction mixture was reduced by km and washed with a small amount of ethanol, resulting in 2
, 5v colorless crystals are obtained. Melting point 161-2°C, yield 59.0% 1-(3-methulfenyl)-5-phenyl-1,2,
4-triazole-3-carboxamide (in the formula ①, R2 and R3 are hydrogen atoms, 1t is a methyl group at the 3-position) 2.8 f (0.01 mol) (i7 toluene 5
Suspend in 0 ml of methoxyacetyl chloride 1.3
y (0,012 mol) and refluxed for 2 hours.
反応混合物を濃縮し少量のエタノールで洗浄すると、2
.12の無色結晶が得られる。jslt点128〜30
℃、収率60%
次に実施例の若干をあげるが、相体(1@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。The reaction mixture was concentrated and washed with a small amount of ethanol, resulting in 2
.. 12 colorless crystals are obtained. jslt points 128-30
℃, yield 60% Next, some examples will be given, but the mixing ratio of the phase (1 @ diluent) and the auxiliary agent and the active ingredients can be varied within a wide range.
実施例1;水和剤
化合物A3 50部リグニン
スルホン酸塩 5部アルキルスル
ホン酸塩 3部珪藻土
42部全混合粉砕し水利剤とし、
水で稀釈して使用する。Example 1; Wettable powder compound A3 50 parts lignin sulfonate 5 parts alkyl sulfonate 3 parts diatomaceous earth
All 42 parts are mixed and crushed and used as an irrigation agent.
Use by diluting with water.
実施例2:乳剤
化合物厘10 25部キシレ
ン 65部ポリオキシエ
チレンアルキルアリル
エーテル 10部を均一
混合し乳剤とし水で稀釈して使用する。Example 2: Emulsion compound 10 parts 25 parts xylene 65 parts polyoxyethylene alkyl allyl ether 10 parts are uniformly mixed to form an emulsion, which is diluted with water and used.
実施例3:粒剤
化合@属12 8部ベントナイト
40部クレー
45部リグニンスルホン酸塩
7部を均一に混合し、史に水を加え練合せ、押出式造
粒機で粒状に力[1工、乾燥して粒剤とする。Example 3: Granule compound @ Genus 12 8 parts bentonite 40 parts clay
45 parts lignin sulfonate
Mix 7 parts uniformly, add water, knead, grind into granules using an extrusion granulator, and dry to make 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金
示す。Next, some test examples will be shown to demonstrate the effectiveness of the compounds of the present invention.
試雇例t:411を物発芽前土壌処理の除草効果試験プ
ランタ−(f150X210X200瓢)に土壌をつめ
畑地状とし、試験植物の柚子の一定針を播種し覆土した
後、本発明化合物が、了−ル当り50を相当被になるよ
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。Trial employment example T: 411 was used to test the herbicidal effect of pre-emergence soil treatment.The soil was packed in a planter (F150 x 210 x 200 gourd) to make it look like a field, and after sowing a certain number of yuzu needles of the test plant and covering the soil, the compounds of the present invention were tested. - A diluted solution adjusted to cover 50% of the soil was uniformly spread on 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 O殺草効果なし 1 20%の殺草効果 240% 〃 360% 〃 480% 〃 5100% 〃 上記試験の結果全第2表に示す。Evaluation criteria O No herbicide effect 1 20% weed killing effect 240% 360% 480% 5100% The results of the above tests are shown in Table 2.
試験例1と同様操作により播種し、植物が1〜2葉期に
達したときに、有効成分アール当り50?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。The seeds were sown in the same manner as in Test Example 1, and when the plants reached the 1-2 leaf stage, 50? A considerable amount of water suspension was uniformly sprayed on the soil surface of the shoots and leaves, and growth was managed in a greenhouse. The same investigation as in Test Example 1 was conducted 25 days after the treatment.
上記試験の結果全第3表に示す。The results of the above tests are shown in Table 3.
第1図は化合物番号l、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24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2B。Figure 1 shows compound number 1, Figure 2 shows compound number 2, and Figure 3 shows compound number 3. Figure 4 shows compound number 4. Figure 5 shows compound number 5. Figure 6 shows compound number 6. Figure 7 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. Figure 20 shows compound number 20°. Figure 21 shows compound number 21. Figure 22 shows compound number 22. Figure 23 shows compound number 23. Figure 24 shows 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 2B.
第29図は化合物番号29の赤外吸収スペクトル全手続
補正書
特許庁長官 若 杉 和 夫 殿
1、事件の表示 昭和57年 特 願第77010号2
、発明の名称 トリアゾール誘導体及び該誘導体を含
有する除草剤
3、補正をする者
事件との関係 特許出願人
4、 代 理 人 東京都新宿区新宿1丁目1番
14号 山田ビル7、補正の対象 明細書
8、補正の内存
(11明細書中、第2頁最下行の
” J
と補正する。Figure 29 shows the infrared absorption spectrum of Compound No. 29, complete procedure amendment, Commissioner of the Japan Patent Office, Kazuo Wakasugi, 1, case description, 1981, Patent Application No. 77010, 2.
, Title of the invention Triazole derivatives and herbicides containing said derivatives 3, Relationship with the case of the person making the amendment Patent applicant 4, Agent Yamada Building 7, 1-1-14 Shinjuku, Shinjuku-ku, Tokyo, Subject of the amendment Specification 8, Inclusion of amendment (amended as "J" on the bottom line of page 2 of the 11th specification.
(2)明細書中、第7頁を別4iのとお)補正する。(2) Amend page 7 of the specification as per Section 4i).
Claims (2)
シアルキル基金表わし、R2は水素原子、アルキル基、
ハロゲノアルキル基、ヒドロキシアルキル基、シアノア
ルキル基、アセチル基、)・ロゲノアセチル基、メトキ
シアセチル基、アミン基、メトキシ基又は水酸基を表わ
し、R3,R。 はそれぞれ水素原子、アルキル基又はハロゲン原子を表
わす。) 全有する1、2.4−)リアゾール誘導体。(1) General formula (I) 4 (wherein R, l"j represents a hydrogen atom, an alkyl group or a hydroxyalkyl group, R2 is a hydrogen atom, an alkyl group,
R3,R represents a halogenoalkyl group, a hydroxyalkyl group, a cyanoalkyl group, an acetyl group, a )-logenoacetyl group, a methoxyacetyl group, an amine group, a methoxy group, or a hydroxyl group; each represents a hydrogen atom, an alkyl group or a halogen atom. ) All 1,2.4-) lyazole derivatives.
義である)を有する1、2.4−トリアゾール誘導体を
含有する除草剤。(2) A herbicide containing a 1,2,4-triazole derivative having the general formula (1) (wherein 1 + "2 + R8 + "4 has the same meaning as above).
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7701082A JPS58194866A (en) | 1982-05-07 | 1982-05-07 | Triazole derivative and herbicide containing the same |
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 |
BR8302385A BR8302385A (en) | 1982-05-07 | 1983-05-06 | HERBICIDE COMPOSITION |
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 |
---|---|---|---|
JP7701082A JPS58194866A (en) | 1982-05-07 | 1982-05-07 | Triazole derivative and herbicide containing the same |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS58194866A true JPS58194866A (en) | 1983-11-12 |
JPH0360823B2 JPH0360823B2 (en) | 1991-09-17 |
Family
ID=13621780
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP7701082A Granted JPS58194866A (en) | 1982-05-07 | 1982-05-07 | Triazole derivative and herbicide containing the same |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS58194866A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
JP2006501275A (en) * | 2002-09-19 | 2006-01-12 | ソルベイ・フアーマシユーチカルズ・ベー・ブイ | 1H-1,2,4-triazole-3-carboxamide derivatives as cannabinoid-CB1 receptor ligands |
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
- 1982-05-07 JP JP7701082A patent/JPS58194866A/en active Granted
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
US7612105B2 (en) | 1998-04-27 | 2009-11-03 | Kumiai Chemical Industry Co., Ltd. | 3-arylphenyl sulfide derivative and insecticide and miticide |
US7767626B2 (en) | 1998-04-27 | 2010-08-03 | Kumiai Chemical Industry Co., Ltd. | 3-arylphenyl sulfide derivative and insecticide and miticide |
JP2006501275A (en) * | 2002-09-19 | 2006-01-12 | ソルベイ・フアーマシユーチカルズ・ベー・ブイ | 1H-1,2,4-triazole-3-carboxamide derivatives as cannabinoid-CB1 receptor ligands |
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 |
---|---|
JPH0360823B2 (en) | 1991-09-17 |
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