JPH0479338B2 - - Google Patents
Info
- Publication number
- JPH0479338B2 JPH0479338B2 JP5170085A JP5170085A JPH0479338B2 JP H0479338 B2 JPH0479338 B2 JP H0479338B2 JP 5170085 A JP5170085 A JP 5170085A JP 5170085 A JP5170085 A JP 5170085A JP H0479338 B2 JPH0479338 B2 JP H0479338B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- triazole
- dihydro
- soil
- carboxylic acid
- 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 10
- RZMGZEJEAAVXRG-UHFFFAOYSA-N 1,2-dihydrotriazole-3-carboxylic acid Chemical compound N1NN(C=C1)C(=O)O RZMGZEJEAAVXRG-UHFFFAOYSA-N 0.000 claims description 2
- 239000004009 herbicide Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- -1 4,5-dihydro-1,5 -Disubstituted-1H-1,2,4-triazole-3-carboxylic acid amide Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 17
- 239000002689 soil Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000006378 damage Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000234653 Cyperus Species 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- 244000234609 Portulaca oleracea Species 0.000 description 2
- 235000001855 Portulaca oleracea Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical group C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
- KJHCSJNSNZJABT-UHFFFAOYSA-N 2-amino-2-(phenylhydrazinylidene)acetamide Chemical compound NC(=O)C(N)=NNC1=CC=CC=C1 KJHCSJNSNZJABT-UHFFFAOYSA-N 0.000 description 1
- QYTROCIWHAFYTR-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-phenyl-1,3-dihydro-1,2,4-triazole-5-carboxamide Chemical compound N1C(C(=O)N)=NN(C=2C=CC=CC=2)C1C1=CC=C(Cl)C=C1 QYTROCIWHAFYTR-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- 240000004731 Acer pseudoplatanus Species 0.000 description 1
- 235000002754 Acer pseudoplatanus Nutrition 0.000 description 1
- 244000045410 Aegopodium podagraria Species 0.000 description 1
- 235000007237 Aegopodium podagraria Nutrition 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 240000003173 Drymaria cordata Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 235000006485 Platanus occidentalis Nutrition 0.000 description 1
- 244000184734 Pyrus japonica Species 0.000 description 1
- 240000001341 Reynoutria japonica Species 0.000 description 1
- 235000018167 Reynoutria japonica Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 244000197975 Solidago virgaurea Species 0.000 description 1
- 235000000914 Solidago virgaurea Nutrition 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000009363 floriculture Methods 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は一般式（）
（式中、R1は水素原子、低級アルキル基、ハ
ロゲン原子を示し、R2は水素原子、低級アルキ
ル基、ハロゲン原子、低級アルコキシ基、水酸基
を示す）を有する新規な４，５−ジヒドロ−１，
５−ジ置換−１，２，４−トリアゾール−３−カ
ルボン酸アミド及びこれを有効成分とする除草剤
に関するものである。
イネ、コムギ、トウモロコシは重要な作物であ
り、これら作物を雑草害から守り増収をはかるた
めに雑草剤を使用することは欠くことができな
い。最近は有用作物と雑草に同時に処理しても作
物に害を与えずに雑草のみを枯殺する選択的雑草
剤が望まれている。
本発明者らは、この要望に応えるべく種々研究
を積重ねた結果、上記一般式（）で表わされる
新規な４，５−ジヒドロ−１，５−ジ置換−１，
２，４−トリアゾール−３−カルボン酸アミドが
優れた選択的除草作用を有することを見出し本発
明を完成するに至つた。
本発明の一般式（）の化合物（以下、本発明
化合物と略称する）は土壌処理試験及び茎葉処理
試験での除草試験で広葉およびイネ科植物に除草
活性を示し、特に広葉植物に優れた除草作用を示
す。しかもイネ、コムギ、トウモロコシなどの重
要作物に薬害を示さないため水田、畑地とその適
用範囲は広い。また土壌移行性が適度なため果樹
園や花卉栽培へも利用できる。
本発明化合物は下記の反応によつてきわめて簡
便に合成することができる。
すなわち一般式（）で示されるアミノ（フエ
ニルヒドラゾノ）アセトアミドとベンズアルデヒ
ド（）を酸触媒の存在下で脱水反応を行なわせ
る。この際不活性気体雰囲気で反応させると一般
に収率が向上する。この方法によつて合成された
本発明化合物の具体例を１表に示す。
The present invention is based on the general formula () A novel 4,5 - dihydro- 1,
The present invention relates to a 5-disubstituted-1,2,4-triazole-3-carboxylic acid amide and a herbicide containing the same as an active ingredient. Rice, wheat, and corn are important crops, and it is essential to use weed killers to protect these crops from weed damage and increase yields. Recently, there has been a desire for a selective weed agent that can kill only the weeds without harming the crops even if it is applied to useful crops and weeds at the same time. As a result of various studies to meet this demand, the present inventors have discovered a novel 4,5-dihydro-1,5-disubstituted-1, represented by the above general formula ().
The present inventors have discovered that 2,4-triazole-3-carboxylic acid amide has an excellent selective herbicidal action and have completed the present invention. The compound of general formula () of the present invention (hereinafter abbreviated as the compound of the present invention) exhibits herbicidal activity against broad-leaved and gramineous plants in soil treatment tests and foliage treatment tests, and has particularly excellent herbicidal activity against broad-leaved plants. Show action. Furthermore, it has a wide range of applications, including paddy fields and upland fields, as it does not cause any phytotoxicity to important crops such as rice, wheat, and corn. Also, because of its moderate soil transferability, it can be used for orchards and floriculture. The compound of the present invention can be synthesized very easily by the following reaction. That is, amino(phenylhydrazono)acetamide represented by the general formula () and benzaldehyde () are subjected to a dehydration reaction in the presence of an acid catalyst. At this time, the yield is generally improved if the reaction is carried out in an inert gas atmosphere. Specific examples of the compounds of the present invention synthesized by this method are shown in Table 1.
【表】
次に本発明化合物の合成例を掲げる。
合成例 １
５−（４−クロロフエニル）−４，５−ジヒドロ
−１−フエニル−1H−１，２，４−トリアゾー
ル−３−カルボン酸アミド（化合物）の合成：
出発原料式化合物（R1＝Ｈ）1.8gとパラクロ
ルベンズアルデヒド2.1gをパラトルエンスルホン
酸20mgとともにベンゼン50mlに加え、10時間共沸
脱水装置を付して還流した。冷却後、生成物を
取して化合物3.0g（94％収率）を得た。mp213
−５℃，1R（KBr，cm-1）；νNH3380，3260，
3200，νco1660
NMR（d6−DMSO）δ（ppm）：
6.40（1H，Ｓ；CH＜），6.6〜8.1（12H，ｍ；ArH
＋NH＋NH2）
合成例 ２
４，５−ジヒドロ−１−（３−メチルフエニル）
−５−フエニル−1H−１，２，４−トリアゾー
ル−３−カルボン酸アミド（化合物）の合成：
出発原料式化合物（R1＝３−CH3）3.0gとベ
ンズアルデヒド2.1gをパラトルエンスルホン酸25
mgとともに脱気したベンゼン50mlに加え、窒素気
流中で共沸脱水装置を付して３時間還流した。冷
却後結晶を取して4.1g（94％）の化合物を得
た。mp193−５℃，IR（KBr，cm-1）：νNH3380，
3290，3170，νco1660
NMR（d6−DMSO）δ（ppm）：
2.23（3H，Ｓ；CH3），6.50（1H，Ｓ；CH＜），
6.6〜8.4（13H，ｍ；ArH＋NH＋NH2）
MS（ｍ／ｚ，相対強度）：280（M+，55％），279
（20％），278（15％），262（14％），203（100％），
186（78％）
合成例 ３
４，５−ジヒドロ−１−（３−メチルフエニル）
−５−フエニル−1H−１，２，４−トリアゾー
ル−３−カルボン酸アミド（化合物）の合成：
出発原料式化合物（R1＝３−CH3）19.2gと
ベンズアルデヒド11.7gを脱気した酢酸150mlに加
え、室温で窒素気流下で1.5時間撹拌した。結晶
を取し、脱気した酢酸20mlで洗浄した。これを
KOHデシタケータで乾燥して22.5g（80.5％収率）
の化合物を得た。
次に若干の実施例を挙げるが、担体（希釈剤）
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。以下組成は重量部で示す。
実施例 １ 水和剤
化合物 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
を混合粉砕して水和剤とし水で希釈して使用す
る。
実施例 ２ 粒剤
化合物 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
を均一混合し、更に水を加え練合せ押出式造粒機
で粒状に加工乾燥して粒剤とする。
次に本発明化合物の有効性を証するために若干
の試験例を示す。
試験例 １
畑雑草に対する雑草発芽前土壌処理の除草効果
プランター（650×210×200mm）に土壌をつめ畑
地状とし、作物としてトウモロコシ、大豆、綿、
小麦の種子、雑草としてノビエ、コゴメカヤツ
リ、スズメノカタビラ、ハコベ、タネツケバナ、
アメリカセンダングサ、スベリヒユ、イヌビユ、
イヌタデの種子の一定量を播種し、種子がかくれ
る程度の覆土をした後、本発明化合物がアール当
り50g相当量になるように調製した希釈液を土壌
表面に均一に散布し、温室内にて育成管理した。
処理25日後に次の基準にて除草効果、作物に対す
る薬害を調査した。結果を表２に示す。調査基準
除 草 効 果 薬 害
０：効果なし −：無 害
１：20％の除草効果 ±：僅小害
２：40％ 〃 ＋：小 害
３：60％ 〃 ：中 害
４：80％ 〃 ：甚 害
５：100％ 〃 〓：枯 死[Table] Synthesis examples of the compounds of the present invention are listed below. Synthesis Example 1 Synthesis of 5-(4-chlorophenyl)-4,5-dihydro-1-phenyl-1H-1,2,4-triazole-3-carboxylic acid amide (compound): Starting material formula compound (R 1 = 1.8 g of H) and 2.1 g of parachlorobenzaldehyde were added to 50 ml of benzene along with 20 mg of para-toluenesulfonic acid, and the mixture was refluxed for 10 hours using an azeotropic dehydrator. After cooling, the product was removed to obtain 3.0 g (94% yield) of the compound. mp213
-5℃, 1R (KBr, cm -1 ); νNH3380, 3260,
3200, νco1660 NMR ( d6- DMSO) δ (ppm): 6.40 (1H, S; CH<), 6.6-8.1 (12H, m; ArH
+NH+ NH2 ) Synthesis example 2 4,5-dihydro-1-(3-methylphenyl)
Synthesis of -5-phenyl-1H-1,2,4-triazole-3-carboxylic acid amide (compound): 3.0 g of the starting material formula compound (R 1 = 3-CH 3 ) and 2.1 g of benzaldehyde were added to para-toluenesulfonic acid. twenty five
The mixture was added to 50 ml of degassed benzene together with mg, and refluxed for 3 hours in a nitrogen stream using an azeotropic dehydrator. After cooling, the crystals were collected to obtain 4.1 g (94%) of the compound. mp193−5℃, IR (KBr, cm -1 ): νNH3380,
3290, 3170, νco1660 NMR ( d6- DMSO) δ (ppm): 2.23 (3H, S; CH3 ), 6.50 (1H, S; CH<),
6.6-8.4 (13H, m; ArH + NH + NH 2 ) MS (m/z, relative intensity): 280 (M + , 55%), 279
(20%), 278 (15%), 262 (14%), 203 (100%),
186 (78%) Synthesis example 3 4,5-dihydro-1-(3-methylphenyl)
Synthesis of -5-phenyl-1H-1,2,4-triazole-3-carboxylic acid amide (compound): Starting material formula compound (R 1 = 3-CH 3 ) 19.2 g and benzaldehyde 11.7 g degassed acetic acid The mixture was added to 150 ml and stirred at room temperature under a nitrogen stream for 1.5 hours. The crystals were collected and washed with 20 ml of degassed acetic acid. this
22.5g (80.5% yield) dried in KOH desiccator
The compound was obtained. Next, some examples are given, but carrier (diluent)
and auxiliaries, their mixing ratios and active ingredients can vary within a wide range. The composition below is shown in parts by weight. Example 1 Wettable powder Compound 50 parts Lignosulfonate 5 parts Alkyl sulfonate 3 parts Diatomaceous earth 42 parts are mixed and pulverized to form a wettable powder and used by diluting with water. Example 2 Granules 8 parts of compound, 40 parts of bentonite, 45 parts of clay, and 7 parts of lignin sulfonate are mixed uniformly, water is further added, and the mixture is kneaded and processed into granules using an extrusion type granulator and dried to obtain granules. Next, some test examples will be shown to demonstrate the effectiveness of the compounds of the present invention. Test example 1 Herbicidal effect of soil treatment before weed germination on field weeds Fill a planter (650 x 210 x 200 mm) with soil to prepare a field, and use corn, soybeans, cotton,
Wheat seeds, weeds such as wild grass, cyperus japonica, sycamore, chickweed, and ashweed.
American purslane, purslane, goldenrod,
After sowing a certain amount of Japanese knotweed seeds and covering the soil with enough soil to cover the seeds, a diluted solution of the compound of the present invention prepared in an amount equivalent to 50 g per area was uniformly sprinkled on the soil surface and placed in a greenhouse. The children were raised and managed.
25 days after treatment, herbicidal effects and chemical damage to crops were investigated using the following criteria. The results are shown in Table 2. Research standard weeding effect medicine Harm 0: No effect -: No harm 1: 20% herbicidal effect ±: Slight harm 2: 40% 〃 +: Slight harm 3: 60% 〃: Medium harm 4: 80%〃 : Severe damage 5: 100% 〃 〓: Withering
【表】【table】
【表】
試験例 ２
畑雑草に対する雑草発生始期処理の除草効果
試験例１と同様の操作により播種した作物及び
雑草が１〜２葉期に達した時に、有効成分アール
当り50g相当量の水懸濁液を茎葉部、土壌表面に
均一に散布し、温室内にて育成処理した。処理25
日後に試験例１と同様に調査した。結果を次頁の
表３に示す。[Table] Test Example 2 Herbicidal effect of treatment at the beginning of weed emergence on field weeds When the crops and weeds sown by the same procedure as Test Example 1 reached the 1st to 2nd leaf stage, an amount of water equivalent to 50g per active ingredient R was applied. The suspension was uniformly sprayed on the stems, leaves, and soil surface, and the plants were grown in a greenhouse. processing 25
A day later, the same investigation as in Test Example 1 was conducted. The results are shown in Table 3 on the next page.
【表】
試験例 ３
水田雑草に対する雑草発生前及び発生後土壌処理
の除草効果
１／5000アールポツトに土壌をつめ水田状態と
し、ノビエ及びカヤツリグサをそれぞれ３葉期、
２葉期及び発生前（pre）となるように調整した。
さらに薬剤処理の３日前に2.5葉期の種苗イネを
移植した。これに有効成分アール当り30g相当量
の水懸濁液を注入し、温室内で育成管理した。処
理25日後に試験例１と同様の調査基準にて調査し
た。結果を次頁の表４に示す。[Table] Test Example 3 Herbicidal effect of soil treatment before and after weed emergence on paddy field weeds Soil was packed in a 1/5000 are pot to create a paddy field condition, and wildflowers and cyperus were grown at the 3-leaf stage, respectively.
It was adjusted to be at the two-leaf stage and before emergence (pre).
Furthermore, seedling rice at the 2.5 leaf stage was transplanted 3 days before the chemical treatment. A water suspension equivalent to 30 g per active ingredient R was injected into this, and the plants were grown in a greenhouse. 25 days after the treatment, an investigation was conducted using the same investigation criteria as in Test Example 1. The results are shown in Table 4 on the next page.
【表】【table】
Claims (1)
ゲン原子を示し、R2は水素原子、低級アルキル
基、ハロゲン原子、低級アルコキシ基、水酸基を
示す）を有する４，５−ジヒドロ−１，５−ジ置
換−1H−１，２，４−トリアゾール−３−カル
ボン酸アミド。 ２ 一般式 （式中R1とR2は前記のものと同じ）を有する
４，５−ジヒドロ−１，５−ジ置換−1H−１，
２，４−トリアゾール−３−カルボン酸アミドを
含有する除草剤。[Claims] 1. General formula (In the formula, R 1 represents a hydrogen atom, a lower alkyl group, or a halogen atom, and R 2 represents a hydrogen atom, a lower alkyl group, a halogen atom, a lower alkoxy group, or a hydroxyl group.) 4,5-dihydro-1,5 -Disubstituted-1H-1,2,4-triazole-3-carboxylic acid amide. 2 General formula 4,5-dihydro-1,5-disubstituted-1H-1 having (wherein R 1 and R 2 are the same as above),
A herbicide containing 2,4-triazole-3-carboxylic acid amide.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5170085A JPS61210075A (en) | 1985-03-15 | 1985-03-15 | Dihydrotriazole and herbicide |
| DE8686300373T DE3677790D1 (en) | 1985-01-23 | 1986-01-20 | DIHYDROTRIAZOLE DERIVATIVES AND THEIR USE AS HERBICIDES. |
| EP86300373A EP0189300B1 (en) | 1985-01-23 | 1986-01-20 | Dihydrotriazole derivatives and their use as herbicides |
| US06/820,948 US4902805A (en) | 1985-01-23 | 1986-01-21 | Derivatives of dihydrotriazole, and herbicidal compositions containing the same as an active ingredient |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5170085A JPS61210075A (en) | 1985-03-15 | 1985-03-15 | Dihydrotriazole and herbicide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61210075A JPS61210075A (en) | 1986-09-18 |
| JPH0479338B2 true JPH0479338B2 (en) | 1992-12-15 |
Family
ID=12894172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5170085A Granted JPS61210075A (en) | 1985-01-23 | 1985-03-15 | Dihydrotriazole and herbicide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61210075A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1023222C (en) * | 1987-03-18 | 1993-12-22 | 吴羽化学工业株式会社 | Derivative of 4,5-dihydro-1H-1,2,4-Triazole-3-carboxamide, intermediate for producing derivative and herbicidal composition containing derivative |
| JPH0778045B2 (en) * | 1987-03-19 | 1995-08-23 | 呉羽化学工業株式会社 | 1,5-Diphenyl-1H-1,2,4-triazol-3-carboxylic acid amide derivative and herbicide containing the derivative |
| JPH0778046B2 (en) * | 1987-03-27 | 1995-08-23 | 呉羽化学工業株式会社 | 4,5-Dihydro-1H-1,2,4-triazole-3-carboxylic acid amide derivative, method for producing the same and herbicide containing the derivative |
| KR100345850B1 (en) * | 1997-01-06 | 2002-11-29 | 주식회사 엘지씨아이 | 1-Benzyl-4,5-dicarbonyl-1,2,3-triazole derivative and process for preparation thereof |
| KR100345849B1 (en) * | 1997-01-06 | 2002-11-30 | 주식회사 엘지씨아이 | 1-Benzyl-1,2,3-triazolecarboxylic acid derivative and process for preparation thereof |
| KR100345852B1 (en) * | 1997-01-06 | 2002-11-29 | 주식회사 엘지씨아이 | 1-benzyl-4,5-dicarbonyl-1,2,3-triazole derivatives and preparation process thereof |
-
1985
- 1985-03-15 JP JP5170085A patent/JPS61210075A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61210075A (en) | 1986-09-18 |
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