CN1076583C - 一种使植物干枯和/或脱叶的方法 - Google Patents
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- 238000011160 research Methods 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ZOKXUAHZSKEQSS-UHFFFAOYSA-N tribufos Chemical compound CCCCSP(=O)(SCCCC)SCCCC ZOKXUAHZSKEQSS-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
一种用作调节植物生长的组合物，其中含有至少一种通式(Ⅰ)所表示的3-苯基吡唑衍生物作为有效成分；
作为干枯剂或脱叶剂，可有效地用于根用蔬菜(如马铃薯)、纤维作物(如棉花)、油料作物(如大豆和向日葵)和谷物(如水稻)；以及一种施用上述组合物的方法。
Description
本发明涉及一种用作调节植物生长的组合物及其施用方法。
本发明中使用的，下文用通式(I)所表示的3—取代的苯基吡唑衍生物，是在日本专利待审公开号3—163063和4—211065中描述过的一种化合物。作为一种叶面施用的除草剂，上述衍生物对危害旱地耕作法农田的所有草本杂草具有卓越的除草活性。特别是施用于小麦(大麦、燕麦或黑麦)作物地，上述衍生物对一些典型的杂草表现出显著的除草效果，这些杂草如猪殃殃、繁缕、波斯水苦荬、淡甘菊、小野芝麻、宝盖草、荠菜、沼泽焊菜、粘卷耳、藜、一种蓼(Polygon-um longisetum)、扁蓄等。
需要开发一种新颖的植物生长调节剂(如干枯剂或脱叶剂)，用于使一些作物收获方便，包括根用蔬菜(如马铃薯)、纤维作物(如棉花)、油料作物(如大豆和向日葵)和谷物(如水稻)。本发明人为开发用于调节植物生长的一种新颖组合物进行了认真研究，从而发现已知作为除草剂的一种化合物，即3位取代的吡唑衍生物，可用于制备一种调节植物生长的组合物，如作物根用蔬菜(如马铃薯)、纤维作物(如棉花)、油料作物(如大豆和向日葵)和谷物(如水稻)的干枯剂或脱叶剂。由此构成本发明。
本发明中调节植物生长的组合物的特征是，含有至少一种通式(I)所表示的3位取代的吡唑衍生物作为有效成分。其中R是
—Y1R3(其中R3是一个(C1-6烷基、卤代(C1-6)烷基、(C2-6)链烯基或(C2-6)炔基，同时Y1是—O—或—S—)，
—Y2CH(R4)CO—OR5(其中R4是一个氢原子或一个(C1-6)烷基，R5是一个氢原子、(C1-6)烷基、卤代(C1-6)烷基、(C2-6)链烯基或(C2-6)炔基，同时Y2是—O—、—S—或—NH—)，
—COOCH(R4)CO—Y1R5(其中R4、R5和Y1定义同前)，或
—COOR6(其中R6是一个(C1-6)烷基、卤代(C1-6)烷基、(C2-6)链烯基或(C2-6)炔基，R1是一个(C1-6)烷基，R2是一个氢原子、(C1-6)烷基或卤代(C1-6)烷基，X1和X2是相同或不相同的卤原子，Y是—O—、—S—、—SO—、—SO2—或—NH—，同时n是整数0或1；本发明也涉及上述组合物作为调节植物生长的施用方法。
在通式(I)所表示的3位取代吡唑衍生物的取代基定义中，术语“(C1-6)烷基”意为1至6个碳原子的直链或支链烷基，如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、正己基等。前缀“卤代”是用来描述含有一个或多个氯、氟、溴或碘原子的基团。术语“卤代(C1-6)烷基”意为有取代基的1至6个碳原子的直链或支链烷基，该烷基有一个或多个、相同或不同的氯、氟、溴或碘原子取代基团。术语“(C2-6)链烯基”和“(C2-6)炔基”意为2至6个碳原子的直链或支链烯基和炔基。
作为通式(I)所表示的3—苯基吡唑衍生物的典型化合物，也就是本发明中所用有效成分，列于表1。但并不打算用这些化合物以任何方式限制本发明的范围。
通式(I)
表1(R1＝CH3)
| R | R2 | X1 | X2 | (Y)n | 物理性质 | |
| 12345678910111213141516 | OCH2CH＝CH2OCH2CH＝CH2OCH2CH＝CH2SCH2CH＝CH2SCH2CH＝CH2SCH2CH＝CH2OCH2C≡CHOCH2C≡CHOCH2C≡CHSCH2C≡CHSCH2C≡CHSCH2C≡CHOCH2COOCH3OCH2COOCH3OCH2COOCH3OCH2COOCH3 | CH3CHF2CHF2CH3CHF2CHF2CH3CHF2CHF2CH3CHF2CHF2CH3CHF2CHF2CHF2 | ClClFClClFClClFClClFClClClF | ClClClClClClClClClClClClClClBrCl | SOOSOOSOOSOOSOOO | nD 1.6131(25.3℃)nD 1.5536(28.4℃)m.p.63.7-64.1℃膏状m.p.52.0-55.0℃nD 1.5670(17.9℃)m.p.71.5℃m.p.84.0℃m.p.98.0-98.1℃m.p.94.5℃m.p.127-129℃m.p.82.8℃m.p.126.2℃m.p.119.8℃m.p.133.8℃m.p.122.8-123.1℃ |
-待续-
表1(续)
| R | R2 | X1 | X2 | (Y)n | 物理物质 | |
| 171819202122232425262728293031323334353637 | OCH2COOC2H5OCH2COOC2H5OCH2COOC2H5OCH2COOC3H7-nOCH2COOC3H7-nOCH2COOC3H7-iOCH2COOC3H7-iOCH2COOCH2CH＝CH2OCH2COOCH2CH＝CH2OCH2COOCH2C≡CHOCH2COOCH2C≡CHOCH(CH3)COOHOCH(CH3)COOCH3OCH(CH3)COOCH3OCH(CH3)COOC2H5OCH(CH3)COOC2H5OCH(CH3)COOC2H5OCH(CH3)COOC2H5OCH(CH3)COOC3H7-iSCH(CH3)COOCH3SCH(CH3)COOCH3 | CH3CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CH3CH3CHF2CH3CHF2CHF2CHF2CH3CHF2CHF2 | ClClFClFClFClFClFClClFClClClFClClF | ClClClClClClClClClClClClClClClClBrClClClCl | SOOOOOOOOOOSSOSOOOSOO | m.p.106.5℃m.p.102.3℃m.p.127.6℃m.p.89.7℃m.p.97.6-97.8℃m.p.106.0℃m.p.120.3-120.5℃m.p.84.7℃m.p.89.2-89.4℃m.p.119.6℃m.p.99.0℃m.p.191-194℃m.p.90-93℃m.p.95.6℃nD 1.5763 ( 28.8℃)nD 1.5238(25.7℃)nD 1.5396(20.8℃)m.p.67.0-67.2℃m.p.87-90℃nD 1.5654(19.8℃)nD 1.5494(25.0℃) |
-待续-
表1(续)
| R | R2 | X1 | X2 | (Y)n | 物理性质 | |
| 383940414243444546474849505152535455565758 | SCH(CH3)COOC2H5SCH(CH3)COOC2H5NHCH(CH3)COOCH3NHCH(CH3)COOC2H5NHCH(CH3)COOC2H5NHCH(CH3)COOC2H5COOCH2COOCH3COOCH2COOCH3COOCH2COSCH3COOCH2COSCH3COOCH2COOC2H5COOCH2COOC2H5COOCH2COSC2H5COOCH2COSC2H5COOCH2COOC3H7-iCOOCH2COOC3H7-iCOOCH2COSC3H7-iCOOCH2COSC3H7-iCOOCH2COOCH2CH＝CH2COOCH2COOCH2CH＝CH2COOCH2COOCH2C≡CH | CHF2CHF2CH3CH3CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 | ClFClClClFClFClFClFClFClFClFClFCl | ClClClClClClClClClClClClClClClClClClClClCl | OOSSOOOOOOOOOOOOOOOOO | nD 1.5565(28.0℃)nD 1.5328(18.0℃)m.p.144.2℃膏状nD 1.5371(23.4℃)nD 1.5264(26.6℃)m.p.74.4℃nD 1.5350(27.3℃)m.p.57.2℃nD 1.5362(23.4℃)nD 1.5763(20.7℃)nD 1.5536(27.3℃)nD 1.5289(24.0℃)nD 1.5684(20.2℃)m.p.45.4℃m.p.79.3℃ |
-待续-
表1(续)
| R | R2 | X1 | X2 | (Y)n | 物理性质 | |
| 5960616263646566676869707l7273747576 | COOCH2COOCH2C≡CHCOOCH(CH3)COOCH3COOCH(CH3)COOCH3COOCH(CH3)COOC2H5COOCH(CH3)COOC2H5COOCH2C≡CHCOOCH3COOCH3COOC2H5COOC2H5COOC2H5OCH2CH＝CH2OCH2C≡CHOCH2COOCH3OCH2CH＝CH2OCH2C≡CHSCH2COOCH3OCH2CH＝CH2 | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CH3CHF2CHF2CHF2CHF2i-C3H7i-C3H7i-C3H7t-C4H9CH2Br | FClFClFClClFClClFClClClClClClCl | ClClClClClClClClClClClClClClClClClCl | OOOOOOOOOOONHNH----- | nD 1.5370(25.7℃)nD 1.5314(23.0℃)nD 1.5672(26.0℃)nD 1.5212(14.1℃)m.p.78.5℃m.p.63.9℃nD 1.5430(17.0℃)nD 1.6029(20.1℃)nD 1.5446(26.8℃)nD 1.5320(21.0℃)m.p.80.6℃m.p.118.9℃膏状膏状膏状膏状膏状 |
本发明的作为调节植物生长的组合物，能按照通常配制农药的方式加工成乳油、可湿性粉剂、含水悬浮剂等形式。配制方法是，将一种或多种通式(I)所表示的3—苯基吡唑衍生物，以按重量计，以每100份组合物中含有0.1至90份的比例，与一种或多种含有适宜的固体载体或液体载体以及任选的助剂等材料相混合而成。
本发明的作为调节植物生长的组合物，可作为干枯剂或脱叶剂使用，如用于根用蔬菜(如马铃薯)、纤维作物(如棉花)、油料作物(如大豆和向日葵)和谷物(如水稻)。但并不打算用这些应用实例以任何方式限制本发明的范围。
本发明的作为调节植物生长的组合物，为了某些目的如减少使用剂量，可以含有调节植物生长的其他有效成分。这些其他有效成分的实例如下文。
当用作干枯剂时，该组合物可以与下列例子的药剂相混合。季铵盐类如百草枯、敌草快等；有机磷化合如草甘膦、N—(膦酰甲基)甘氨酸三甲基锍盐(通用名称glyphosate trimecium)、乙烯利等；无机化合物如氯酸钠、氯酸镁、氨、石灰氮(Ca(NCN)/CaCN2)等；脂族化合物如一氯醋酸钠、三氯醋酸钠、六氯丙酮等；酚类化合物如地乐酚、五氯酚及其盐等；三嗪类化合物如莠灭津等；砷酸类化合物如砷酸等；机油；和7—氧杂双环[2，2，1]庚烷—2，3—二羧酸(通用名称草藻灭)及其胺盐、钠盐或钾盐。
当用作脱叶剂时，该组合物可以与下列例子的药剂相混合。有机磷化合物如乙烯利、S，S，S—三丁基三硫代磷酸酯、S，S，S—三丁基三硫代亚磷酸酯等；无机化合物如石灰氮、氯酸钠、硝酸铵、硫氰酸铵、氯化锌、次氯酸钠等；砷酸类化合物如甲基胂酸及其盐等；脂族化合物如氯乙酸等；草藻灭；杀草强；硫脲。并不打算以任何方式用化合物实例限制本发明的范围。
本发明的典型实施例、试验实施例等作为本发明的实施方案叙述如下，但它们不应被解释为是对本发明范围的限制。
在实施例中，份量都是按重量份量计。
实施例1
第19号化合物 0.4份
Solvesso 200 57.6份
聚氧乙烯十二烷基醚 40.0份
(HLB 10.0)
SP—300SX 2.0份
乳油的制备是混匀上述成分直至溶解。
实施例2至7
用作调节植物生长的组合物是按表2中所列每种配方，用实施例1中相同的方法而制得的。
表2
试验实施例1
| 组合物 | 2 | 3 | 4 | 5 | 6 | 7 |
| 化合物No.19Solvesso 200(Exxon化学公司制造)POE十二烷基醚(HLB 14.0)POE苯乙烯苯基醚(HLB 15.5)POE(10mols)壬基苯基醚POE(12mols)壬基苯基醚POE脂肪酸酯(HLB 9.5)N-甲基-2-吡咯烷酮SP-3005X(制造商TORO KAGAKU K.K.) | 0.276.820.03.0 | 0.457.640.02.0 | 0.456.640.03.0 | 0.455.640.04.0 | 1.076.020.03.0 | 2.577.510.010.0 |
| 100.0 | 100.0 | 100.0 | 100.0 | 100.0 | 100.0 |
对马铃薯的干枯效果
马铃薯块茎(栽培品种：May Queen)按行距1.0米、株距0.4米移栽。当生育期达到开始黄化，用实施例1中描述的本发明作为调节植物生长的组合物和参照药剂，每种按预先拟定的剂量对茎叶均匀处理，组合物和参照药剂的药液喷洒体积为1000升/公顷。
处理7天和14天后，茎和叶的干枯效果按下述标准用目测法评价。
另外，处理14天后，块茎被挖出来，维管束褐化的程度按下述标准中的指数来评价。评价干枯效果的标准：
效力 茎和叶的枯萎面积(％)
1 0—49
2 50—69
3 70—89
4 90—99
5 100评价维管束褐化的标准(指数)：
0：维管束无褐化
l：近基部的维管束有轻微褐化
2：少于1/3至2/3维管束褐化
4：全部维管束褐化
表3列出检查干枯效能的结果，表4列出评价维管束褐化的结果。
表3干枯效果
注：采用的一种商品石灰氮(含50％氰氨化钙).AI意为有效成分
| 试验药剂 | 剂量(gAI/ha) | 叶 茎 | ||||
| 7天后 | 14天后 | 7天后 | 14天后 | |||
| 本发明 | 实施例1 | 102040 | 455 | 555 | 344 | 455 |
| 参照 | 敌草快 | 900 | 5 | 5 | 3 | 4 |
| 石灰氮 | 15kg/10a | 4 | 5 | 1 | 4 | |
表4维管束的褐化
| 试验药剂 | 剂量(gAI/ha) | 维管速褐化百分数(％)维管束褐化指数 | |||||
| 0 | 1 | 2 | 3 | 4 | |||
| 本发明 | 实施例1 | 102040 | 1007570 | 02530 | 000 | 000 | 000 |
| 参照 | 敌草快 | 900 | 0 | 56 | 44 | 0 | 0 |
| 石灰氮 | 15kg/10a | 75 | 25 | 0 | 0 | 0 | |
试验实施例2
棉花种子(栽培品种：Acala)按株行距0.4m播下和生长。当棉桃开裂时，用实施例1中描述的本发明调节植物生长的组合物和参照药剂，每种按预先拟定的剂量对叶片均匀处理，药液体积为250升/公顷。
处理后5、10、15和20天，对叶片的干枯效果用目测法评价，评价的幅度由0(与不处理的结果相同)到100(完全枯萎)。至于脱叶效果，处理后15和20天按下列公式计算脱叶率。
另外，处理25天后，调查对棉绒(收获物)的药害，并按下述标准给予评价。脱叶率：
评价对棉绒药害的标准：
+：显现出药害
-：不表现出药害
表5列出检查枯叶效果的结果，表6列出检查脱叶效果的结果和调查对棉绒药害的结果。
表5
| 试验药剂 | 剂量(gAI/ha) | 对叶片干枯效果 | ||||
| 5天后 | 10天后 | 15天后 | 25天后 | |||
| 本发明 | 实施例1 | 51020 | 808090 | 909095 | 939597 | 100100100 |
| 参照 | 敌草快 | 1000 | 90 | 95 | 98 | 100 |
表6
| 试验药剂 | 剂量(gAI/ha) | 脱叶效果 药害(棉绒) | |||
| 15天后 | 25天后 | 25天后 | |||
| 本发明 | 实施例1 | 51020 | 303040 | 707075 | --- |
| 参照 | 敌草快 | 1000 | 8 | 10 | - |
Claims (3)
1.一种使植物干枯和/或脱叶的方法，包括，施用作为干枯剂或脱叶剂的一种组合物，该组合物含有至少一种通式(I)所表示的3位取代的吡唑衍生物作为有效成份：
其中R是
—Y1R3
其中R3是一个(C1-6)烷基、卤代(C1-6)烷基、(C2-6)链烯基或(C2-6)炔基，同时Y1是—O—或—S—，
或R是—Y2CH(R4)CO—OR5
其中R4是一个氢原子或一个(C1-6)烷基，
R5是一个氢原子、(C1-6)烷基、卤代(C1-6)烷基、(C2-6)链烯基或C2-6炔基，同时
Y2是—O—、—S—或—NH—，
或R是一个—COOR6
其中R6是一个(C1-6)烷基、卤代(C1-6)烷基、(C2-6)链烯基或(C2-6)炔基，
R1是一个(C1-6)烷基，R2是一个氢原子、(C1-6)烷基或卤代(C1-6)烷基，
X1和X2是相同或不同相同的卤原子，Y是—O—、—S—、—SO—、—SO2—或—NH—，同时n是整数0或1，其施用剂量为每公顷5至500克，按有效成分计。
2.按照权利要求1的使植物干枯和/或脱叶的方法，其中通式(I)所表示的3位取代的吡唑衍生物是2—氯—5—(4—氯—5—二氟甲氧基—1—甲基—1H—吡唑—3—基)—4—氟苯氧乙酸乙酯。
3.按照权利要求1的使植物干枯和/或脱叶的方法，其中植物是根用蔬菜如马铃薯、纤维作物如棉花、油料作物如大豆和向日葵、谷物如水稻。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22741895A JP3663522B2 (ja) | 1995-08-12 | 1995-08-12 | 植物生育調節用組成物及びその使用方法 |
| JP227418/1995 | 1995-08-12 | ||
| JP227418/95 | 1995-08-12 |
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| CN1142891A CN1142891A (zh) | 1997-02-19 |
| CN1076583C true CN1076583C (zh) | 2001-12-26 |
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| CN96109429A Expired - Lifetime CN1076583C (zh) | 1995-08-12 | 1996-08-09 | 一种使植物干枯和/或脱叶的方法 |
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|---|---|
| US (1) | US6117818A (zh) |
| EP (1) | EP0787429B1 (zh) |
| JP (1) | JP3663522B2 (zh) |
| CN (1) | CN1076583C (zh) |
| AR (1) | AR003229A1 (zh) |
| AU (1) | AU690465B2 (zh) |
| BR (1) | BR9603370A (zh) |
| CA (1) | CA2182773C (zh) |
| DE (1) | DE69617895T2 (zh) |
| ES (1) | ES2169181T3 (zh) |
| HU (1) | HU216748B (zh) |
| PL (1) | PL187690B1 (zh) |
| RU (1) | RU2140154C1 (zh) |
| TR (1) | TR199600650A2 (zh) |
| UA (1) | UA55366C2 (zh) |
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| JP5113531B2 (ja) * | 2006-01-16 | 2013-01-09 | 三井化学アグロ株式会社 | （３−硫黄原子置換フェニル）ピラゾール誘導体 |
| NZ603156A (en) | 2010-03-30 | 2014-10-31 | Verseon Corp | Multisubstituted aromatic compounds as inhibitors of thrombin |
| JP2014159374A (ja) * | 2011-05-20 | 2014-09-04 | Nippon Nohyaku Co Ltd | 作物の枯凋落葉剤組成物 |
| CN105209440B (zh) * | 2013-03-15 | 2019-07-23 | 维颂公司 | 作为凝血酶抑制剂的卤代吡唑 |
| BR112015022340A2 (pt) | 2013-03-15 | 2017-07-18 | Verseon Corp | método para tratamento ou prevenção de uma doença ou distúrbio relacionado à calicreína em um sujeito, composto, e, composição farmacêutica |
| EP3110252A1 (en) | 2014-02-28 | 2017-01-04 | Drexel Chemical Company | Compositions and methods for improving seed quality |
| AU2015317522A1 (en) | 2014-09-17 | 2017-03-23 | Verseon Corporation | Pyrazolyl-substituted pyridone compounds as serine protease inhibitors |
| MX2017011000A (es) | 2015-02-27 | 2017-10-20 | Verseon Corp | Compuestos de pirazol sustituidos como inhibidores de serina proteasa. |
| CN107593721B (zh) * | 2017-10-19 | 2019-06-04 | 中国农业科学院麻类研究所 | 一种大麻脱叶的方法、脱叶剂及其应用 |
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| US5112384A (en) * | 1990-02-28 | 1992-05-12 | Nihon Nohyaku Co., Ltd. | 3-(substituted phenyl) pyrazole derivatives herbicidal composition containing the same and method of controlling weeds using said composition |
| CN1091586A (zh) * | 1993-02-06 | 1994-09-07 | 日本农药株式会社 | 一种低植物毒性的除草剂组合物 |
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| KR930004672B1 (ko) * | 1988-08-31 | 1993-06-03 | 니혼 노야꾸 가부시끼가이샤 | 3-치환 페닐피라졸 유도체 또는 이의 염 및 이의 제조방법, 이의 용도 및 이의 사용 방법 |
| JP2887701B2 (ja) * | 1990-02-28 | 1999-04-26 | 日本農薬株式会社 | ３−置換フェニルピラゾール誘導体又はその塩類及びその用途 |
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- 1996-08-02 DE DE69617895T patent/DE69617895T2/de not_active Expired - Lifetime
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- 1996-08-07 TR TR96/00650A patent/TR199600650A2/xx unknown
- 1996-08-07 US US08/693,967 patent/US6117818A/en not_active Expired - Lifetime
- 1996-08-09 CN CN96109429A patent/CN1076583C/zh not_active Expired - Lifetime
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- 1996-08-09 AR ARP960103938A patent/AR003229A1/es active IP Right Grant
- 1996-08-09 RU RU96116142A patent/RU2140154C1/ru active
- 1996-08-09 UA UA96083207A patent/UA55366C2/uk unknown
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5112384A (en) * | 1990-02-28 | 1992-05-12 | Nihon Nohyaku Co., Ltd. | 3-(substituted phenyl) pyrazole derivatives herbicidal composition containing the same and method of controlling weeds using said composition |
| CN1091586A (zh) * | 1993-02-06 | 1994-09-07 | 日本农药株式会社 | 一种低植物毒性的除草剂组合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2169181T3 (es) | 2002-07-01 |
| CN1142891A (zh) | 1997-02-19 |
| JP3663522B2 (ja) | 2005-06-22 |
| HU9602201D0 (en) | 1996-10-28 |
| DE69617895D1 (de) | 2002-01-24 |
| EP0787429A2 (en) | 1997-08-06 |
| US6117818A (en) | 2000-09-12 |
| CA2182773C (en) | 1999-09-07 |
| AU6191196A (en) | 1997-03-20 |
| HU216748B (hu) | 1999-08-30 |
| CA2182773A1 (en) | 1997-02-13 |
| HUP9602201A3 (en) | 1997-09-29 |
| AU690465B2 (en) | 1998-04-23 |
| PL315612A1 (en) | 1997-02-17 |
| EP0787429B1 (en) | 2001-12-12 |
| EP0787429A3 (en) | 1997-11-19 |
| JPH0959113A (ja) | 1997-03-04 |
| PL187690B1 (pl) | 2004-09-30 |
| HUP9602201A2 (en) | 1997-05-28 |
| BR9603370A (pt) | 1998-05-12 |
| RU2140154C1 (ru) | 1999-10-27 |
| UA55366C2 (uk) | 2003-04-15 |
| AR003229A1 (es) | 1998-07-08 |
| TR199600650A2 (tr) | 1997-02-21 |
| DE69617895T2 (de) | 2002-04-25 |
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