JPS58185572A - Triazole derivative and herbicide containing said derivative - Google Patents
Triazole derivative and herbicide containing said derivativeInfo
- Publication number
- JPS58185572A JPS58185572A JP6979182A JP6979182A JPS58185572A JP S58185572 A JPS58185572 A JP S58185572A JP 6979182 A JP6979182 A JP 6979182A JP 6979182 A JP6979182 A JP 6979182A JP S58185572 A JPS58185572 A JP S58185572A
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Abstract
Description
【発明の詳細な説明】
本発明は、 一般式(1)
(式中、R8は水素原子又はアルキル基を表わし、mH
O,1又は2を表わし、R1はアルキル基、アルコキシ
ル基、ニトロ基又はノへロゲ/原子倉表わし、n ri
l又は2を表わす)
で示される倉現なj、 2 、4− )リアゾール誘導
体及びこれ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 (1) (wherein R8 represents a hydrogen atom or an alkyl group, and mH
represents O, 1 or 2, R1 represents an alkyl group, an alkoxyl group, a nitro group or a nitrogen/atomic chain, n ri
The present invention relates to a natural j, 2, 4-) lyazole derivative represented by (representing l or 2) and a herbicide containing the same 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
(1)で表わされる1、2.4−)リアゾール誘導体が
優れた実用的除草効果を有することを発見し、本発明に
至った。As a result of various studies, the present inventors discovered that the 1,2,4-) lyazole derivative represented by the above general formula (1) has an excellent practical herbicidal effect, leading to the present invention. .
本発明の一般式(+)の化合物(以下、本発明化合物と
略称する)は、イネ、小麦、トウモロコシ、棉等に楽4
!rを生ずることなく、種子発芽試験、土壌処理試験、
茎葉敗布処理試験等の除草試練で広#iWi物及びイネ
科m物に対して除草活性を示し、特に広Jam<スベリ
ヒエ、シロザ、タネツケバナ、イヌビエ等)には優れ九
除菫活性金示す。その除草剤としての施用範囲は、水田
、畑地、果樹園等の奥耕地の地、花丹栽培への使用があ
げられる。The compound of the general formula (+) of the present invention (hereinafter abbreviated as the compound of the present invention) can be easily applied to rice, wheat, corn, cotton, etc.
! Seed germination test, soil treatment test, without causing r.
In weeding tests such as stem and leaf rot treatment tests, it has shown herbicidal activity against broad grasses and grasses, and is particularly effective against broad jams (purslane, whitewort, ash, grasshopper, etc.). The scope of its application as a herbicide includes use in paddy fields, upland fields, deep cultivated areas such as orchards, and for flower cultivation.
本発明化合物は、ジアゾニウム塩と馬尿酸との反応によ
り得られる4−フェニルヒドラゾノ−2−フェニルオキ
サゾリン−5−オン(1)t、29%NH4OH(54
,9倍モル量)/メタノール溶液中、還流することによ
り合成され得る。The compound of the present invention is 4-phenylhydrazono-2-phenyloxazolin-5-one (1) obtained by the reaction of diazonium salt and hippuric acid, 29% NH4OH (54
, 9 times the molar amount)/methanol solution by refluxing.
(−)n
(参考文献;ジャーナル・オン・ザ・アメリカン・ケミ
カル・ソサイーテイ、 79 % 、 1956貞。(-)n (Reference: Journal on the American Chemical Society, 79%, 1956).
1957年)。また、式(曹)の化合物音アセト/中、
29%NH,OH(1,3倍モル量)溶液と還流工作用
させ、次いで濃j醸全用いることによっても合成できる
。後者の方法ハ、前者に比べてアンモニア水溶液及び溶
媒の1史用量が少くて、反応波処理がd易であるため有
利である。(1957). Also, the compound sound aceto/in the formula (sodium carbonate),
It can also be synthesized by refluxing with a 29% NH,OH (1.3 times the molar amount) solution and then using Kojjozen. The latter method is advantageous compared to the former because the amount of ammonia aqueous solution and solvent per cycle is smaller and the reaction wave treatment is easier.
本発明化合物の具体別とその理化学的性質t−第1表に
下す。Specific details of the compounds of the present invention and their physical and chemical properties are shown in Table 1.
なお、第1表には各化合物番号に対応する礪遺式會示し
た。Note that Table 1 shows the formulas corresponding to each compound number.
60 次に本発明化合物の合成例を以下に示す。60 Next, a synthesis example of the compound of the present invention will be shown below.
会成例1:化合物番号3の合成
O−メチル馬尿酸5,6fと酢酸ナトリウム(無水物)
S、Ztを無水酢酸24d中、50℃で30分間、つい
で水冷下撹拌する。そこへ、別に3,4−キシリジン3
.2を食酢#!17−と3s%塩酸4.9−の温合物に
とかし氷水冷却下、亜硝酸イソアルミル3.88sgt
滴下してl1ilijilシた3、4−ジメチルフェニ
ルジアゾニウムクロリド溶*を滴下する。滴下IIIk
30分間攪拌し生成する黄色の結晶をIa取して、吸引
下水ついでアセトンで洗浄し中間原料1に得る。Synthesis Example 1: Synthesis of Compound No. 3 O-methyl hippuric acid 5,6f and sodium acetate (anhydride)
S and Zt were stirred in 24 d of acetic anhydride at 50° C. for 30 minutes and then cooled with water. There, separately 3,4-xylidine 3
.. 2 with vinegar #! 17- and 3s% hydrochloric acid 4.9- and cooled with ice water, 3.88 sgt of isoalumyl nitrite
Add dropwise 3,4-dimethylphenyldiazonium chloride solution*. Dripping IIIk
After stirring for 30 minutes, the resulting yellow crystals were collected as Ia, and washed under suction with water and then with acetone to obtain Intermediate Raw Material 1.
これをアセト/γ0−に分散し、29Xアンモニア水溶
液5−を加えて20分間還流する0次に35%塩a15
−會加えて10分間還流して、反応混合物を室温までさ
ます。氷水300−に上記反応混合豐tそそぎ、析出物
上濾取する。エタノールから再結晶して黄色結晶の目的
@t4た。(収量5、:M、収率68%)。m、p、1
88〜190℃;■R(第3図に示す)。Disperse this in acetate/γ0-, add 29X ammonia aqueous solution 5- and reflux for 20 minutes. Next, 35% salt a15
- Add and reflux for 10 minutes and allow the reaction mixture to cool to room temperature. Pour the reaction mixture into 300ml of ice water and filter the precipitate. Recrystallization from ethanol yielded yellow crystals @t4. (Yield 5:M, yield 68%). m, p, 1
88-190°C; ■R (as shown in Figure 3).
可成’f’J2:化合切番号7の合成
p−メチル馬尿酸5.6tと酢酸ナトリウム(無水物)
5.2Fを無水酢酸24−中、50℃で30分間、つい
で水冷下撹拌する。そこへ、別にアニソ72.34−を
酢酸17−と35%塩酸4.9−の混合物にとかし氷水
冷却下、亜bs酸イノアミル3.88−1−M下して調
製し九フェニルンアゾニウムクロリド溶液を滴下する。Compound 'f'J2: Synthesis of compound number 7 p-methylhippuric acid 5.6t and sodium acetate (anhydride)
5.2F was stirred in 24-mL acetic anhydride at 50°C for 30 minutes, then under water cooling. Separately, aniso 72.34- was dissolved in a mixture of acetic acid 17- and 35% hydrochloric acid 4.9-, and under ice water cooling, 3.88-1 M of inoamyl bsite was prepared. Add the chloride solution dropwise.
滴下後30分間攪拌し生成する黄色の結晶【a取して、
吸引下水ついでアセトンで洗浄し中間原料を得る。After dropping, stir for 30 minutes and generate yellow crystals [a]
The intermediate raw material is obtained by suctioning sewage and washing with acetone.
こntアセトン70−に分散し、29%アンモニア水溶
液5wtを加えて20分間還流する。次に、35%1#
5−を加えて10分間還流して、反応混合拗音室温まで
さます。氷水300sjに上記反応混合#IJをそそぎ
析出物を濾取する。エタノールから再結晶して白色結晶
の目的@f:4!4た。(収置4.8F、収$ 67
X)、 m、 p、 ls5−156℃;IR(第1図
に示す)。This was dispersed in 70% of acetone, 5 wt of a 29% ammonia aqueous solution was added, and the mixture was refluxed for 20 minutes. Then 35% 1#
Add 5- and reflux for 10 minutes, and allow the reaction mixture to cool to room temperature. Pour the above reaction mixture #IJ into 300 sj of ice water and collect the precipitate by filtration. Recrystallized from ethanol to obtain white crystals @f:4!4. (Location: 4.8F, storage: $67
X), m, p, ls5-156°C; IR (as shown in Figure 1).
ピ成例3;化酋物番号23の合成
p−クロロ馬尿酸5.6fと酢酸ナトリウム(無水物)
s、zrを無水酢酸24−中、50℃で30分間、つい
で水冷下撹拌する。そこへ、別にm−トルイジン2.7
2ssgt酢酸1フーと35%塩#4.9−の混合物に
とかし氷水冷却下、亜硝酸イソアミル3.88mt滴下
してl1lllilllilした3−メチルフェニルジ
アゾニウムクロリド溶液1に滴下する0滴下後鉛分関攪
拌し生成する黄色の結晶t−瀘濾取て、吸引下水ついで
アセトンで洗浄し中間原料を得る。Example 3: Synthesis of compound number 23 p-chlorohippuric acid 5.6f and sodium acetate (anhydride)
s and zr were stirred in 24-acetic anhydride at 50° C. for 30 minutes, then under water cooling. There, separately m-toluidine 2.7
Dissolve in a mixture of 2ssgt acetic acid 1 and 35% salt #4.9, add dropwise 3.88mt of isoamyl nitrite under cooling with ice water, and add dropwise to 1lllilllil 3-methylphenyldiazonium chloride solution 1. After 0 drops, stir with lead separation. The resulting yellow crystals are filtered through a T-filter, drained under suction, and then washed with acetone to obtain an intermediate raw material.
これをアセトン70−に分散し、29%アンモニア水溶
液S−を加えて20分間還流する1次に35%塩酸5−
を加えて10分間還流して、反応混合物を室温までさま
す。氷水300−に上記反応混合物をそそぎ析出物tI
lllIIiLする。エタノールから再結晶して白色結
晶の目的物を得喪。(収量4.8f、収率65%)。m
、 p、 14g−150℃、 IR(第23図に示す
)。Disperse this in acetone 70-, add 29% ammonia aqueous solution S-, and reflux for 20 minutes. Next, 35% hydrochloric acid 5-
was added and refluxed for 10 minutes, allowing the reaction mixture to cool to room temperature. Pour the above reaction mixture into 300ml of ice water to obtain precipitate tI.
IllIIiL. The desired product was obtained as white crystals by recrystallization from ethanol. (Yield 4.8f, yield 65%). m
, p, 14g-150°C, IR (shown in Figure 23).
次に実施例の若干會あげるが、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。Next, some examples will be given, but the carrier (diluent), the auxiliary agent, the mixing ratio thereof, and the active ingredient can be varied within a wide range.
実施列l:水相剤
化合物A 1 50sリグニン
スルホン酸塩 5部アルキルスル
ホン鈑塩 3811珪噛土
42部金混合粉砕し水和剤と
し、水で稀釈して使用する。Implementation row 1: Water phase agent compound A 1 50s lignin sulfonate 5 parts alkyl sulfone sheet salt 3811 siliceous clay
42 parts of gold are mixed and ground to make a wettable powder, diluted with water, and used.
実施例2:乳剤
化合物A7 25部キシレン
65部ポリオキ7エチレンアル
キル了りルエーテル 10%を均一混合し乳剤とし
、水で稀釈し7て使用する。Example 2: Emulsion compound A7 25 parts xylene
65 parts of polyoxygenate and 10% of ethylene alkyl ether are uniformly mixed to form an emulsion, diluted with water and used.
実施例3:粒剤
化貧@A3 8部
ベントナイト 40部クレー
45部リグニンスルホン
鈑基塩 7部を均一に混合し、艷に水
1に加えて騨合せ、押出式造粒懺で粒状に加工乾燥して
粒剤とする。Example 3: Granulation poor@A3 8 parts bentonite 40 parts clay 45 parts lignin sulfone base salt 7 parts were mixed uniformly, added to 1 part water in a tank, mixed, and processed into granules using an extrusion type granulator. 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賦−例を
示す。Next, some examples will be shown to demonstrate the effectiveness of the compounds of the present invention.
ブラフ / −(850X!10X200% )に土壌
tツkb畑地状とし、試験植物の種子の一定量を播種し
覆土した後、本発明化合物が、アール当りl5ot相当
量になるようKIIIiL次稀釈液を土壌表面に均一に
&布し、温室内にて育生管理した。処[125日債に次
の基準にて評価した。Bluff / - (850X! 10X 200%) was made into a field with 100% of soil, and after sowing a certain amount of seeds of the test plant and covering with soil, the KIIIiL next dilution solution was added so that the compound of the present invention was in an amount equivalent to 150% per area. It was spread evenly on the soil surface and grown in a greenhouse. [125-day bonds were evaluated based on the following criteria.
評4IA基準 O殺草効果なし 1 20%の殺草効果 2 40% # 3 60%の!8箪効果 4 80% # 5 100% M 上記試験の給米を第2表に示す。Evaluation 4IA standards O No herbicide effect 1 20% weed killing effect 2 40% # 3.60%! 8 箪 effect 4 80% # 5 100% M Table 2 shows the rice supply for the above test.
第 2 表
f:、−例2:植物発生始期処理の除皐効果試験試験例
1と同様操作により播棟し、慣物が1〜2頻期に達した
ときに有効成分アール当り50f相当量の水懸濁at茎
茎葉上土壌表面均一に散布し、温室内にて育生管理した
。処理25日恢に試験例1と同様に調査した。上記試験
の結果を第3表に示す。Table 2 f: -Example 2: Test on the effect of removing saplings during treatment at the beginning of plant development.When the seedlings were sown in the same manner as in Test Example 1, and when the habitual matter reached the 1st to 2nd period, an amount equivalent to 50f per active ingredient R was applied. A water suspension of the mixture was sprayed uniformly on the soil surface on the stems, leaves, and grown in a greenhouse. The same investigation as in Test Example 1 was conducted 25 days after the treatment. The results of the above test are shown in Table 3.
第 3 表Table 3
【図面の簡単な説明】
第1図は出汁物番号1、第2図は化付づ番号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10.1511図は化付物番号11
、渠12図は化合物番号12、第13図は化合物番号1
3、第14図11化合物41偏14、第15図は化合脅
番号15、第16図は化合#爵号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
合物袖号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vJ番号24、第2
5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*II号28
、第29図は化合物番号29、第30図は化合物番号3
0.第31図は化合物番号31.432図は化合物番号
32、第33を示す図である。
出−人 (11O,Hh;シ―°1代理人弁理士
宮 111 広 豊代理人弁理七 川 目
我 雄
第1図
第2図
第3図
第4図
第5図
第611
第7図
I8関
第911
第1/ E
第12図
第161i!a
第17図
第18図
第19 III
第20園
第21図
第22図
第23図
第24図
第25!%i
第2611
第2711[Brief explanation of the drawings] Figure 1 is soup stock number 1, Figure 2 is number 2, Figure 3 is compound number 3, Figure 4 is compound number 4, Figure 5 is compound number 5, Figure 6 is compound number 6, Figure 7 is compound number 7, Figure 8 is compound number 8, Figure 9 is compound number 9, Figure 10 is compound number 10.1511 Figure is compound number 11.
, Figure 12 shows compound number 12, and Figure 13 shows compound number 1.
3, Fig. 14 11 Compound 41 Part 14, Fig. 15 shows compound number 15, Fig. 16 shows compound number 16, Fig. 17 shows compound number 17, Fig. 18 shows compound number 18, and Fig. 19 shows compound number 16. Compound number 19 is shown in Figure 20, compound number 20 is shown in Figure 21, and compound number 21 is shown in Figure 21. Figure 22 shows compound number 22, Figure 23 shows compound number 23, Figure 24 shows compound vJ number 24,
Figure 5 shows compound number 25, Figure 26 shows compound number 26, Figure 27 shows compound number 27, and Figure 28 shows compound *II number 28.
, Figure 29 shows compound number 29, Figure 30 shows compound number 3.
0. Figure 31 shows compound number 31. Figure 32 shows compound numbers 32 and 33. Representative (11O, Hh; Sea °1 Patent Attorney Miya 111 Yutaka Hiro Representative Patent Attorney Nanakawa Me
I male Figure 1 Figure 2 Figure 3 Figure 4 Figure 5 Figure 611 Figure 7 I8 Seki No. 911 1/E Figure 12 Figure 161i! a Fig. 17 Fig. 18 Fig. 19 III Fig. 20 Fig. 21 Fig. 22 Fig. 23 Fig. 24 Fig. 25! %i 2611th 2711th
Claims (1)
し、m1jO,1又は2を表わし、R2はアルキル基、
アルコキシル基、ニトロ基又はハロゲン原子t−表わし
、n F′11又は2に−表わす)で示される1、2.
4−)リアゾール−4体。 (2)一般式 (式中、RI+rxJIJ及びnは前記と同義である) で示される1、2.4−トリアゾール誘導体を有効成分
とする除草剤。[Claims] (11 general formula (wherein R1 #-t/j represents a elementary atom or an alkyl group, m1jO represents 1 or 2, R2 is an alkyl group,
1,2.
4-) Riazole-4 bodies. (2) A herbicide containing a 1,2,4-triazole derivative represented by the general formula (wherein RI+rxJIJ and n have the same meanings as above) as an active ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6979182A JPS58185572A (en) | 1982-04-26 | 1982-04-26 | Triazole derivative and herbicide containing said derivative |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6979182A JPS58185572A (en) | 1982-04-26 | 1982-04-26 | Triazole derivative and herbicide containing said derivative |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS58185572A true JPS58185572A (en) | 1983-10-29 |
JPH0360822B2 JPH0360822B2 (en) | 1991-09-17 |
Family
ID=13412920
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP6979182A Granted JPS58185572A (en) | 1982-04-26 | 1982-04-26 | Triazole derivative and herbicide containing said derivative |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS58185572A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0189300A2 (en) * | 1985-01-23 | 1986-07-30 | Kureha Kagaku Kogyo Kabushiki Kaisha | Dihydrotriazole derivatives and their use as herbicides |
EP0297734A2 (en) * | 1987-06-08 | 1989-01-04 | Kureha Kagaku Kogyo Kabushiki Kaisha | A derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide, herbicidal compositions containing the derivative and process for producing the derivative |
US4919707A (en) * | 1987-03-19 | 1990-04-24 | Kureha Kagaku Kogyo Kabushiki Kaisha | Derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide and herbicidal composition containing the same |
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 |
-
1982
- 1982-04-26 JP JP6979182A patent/JPS58185572A/en active Granted
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0189300A2 (en) * | 1985-01-23 | 1986-07-30 | Kureha Kagaku Kogyo Kabushiki Kaisha | Dihydrotriazole derivatives and their use as herbicides |
US4902805A (en) * | 1985-01-23 | 1990-02-20 | Kureha Kagaku Kogyo Kabushiki Kaisha | Derivatives of dihydrotriazole, and herbicidal compositions containing the same as an active ingredient |
EP0189300B1 (en) * | 1985-01-23 | 1991-03-06 | Kureha Kagaku Kogyo Kabushiki Kaisha | Dihydrotriazole derivatives and their use as herbicides |
US4919707A (en) * | 1987-03-19 | 1990-04-24 | Kureha Kagaku Kogyo Kabushiki Kaisha | Derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide and herbicidal composition containing the same |
EP0297734A2 (en) * | 1987-06-08 | 1989-01-04 | Kureha Kagaku Kogyo Kabushiki Kaisha | A derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide, herbicidal compositions containing the derivative and process for producing the derivative |
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 |
Also Published As
Publication number | Publication date |
---|---|
JPH0360822B2 (en) | 1991-09-17 |
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