CN1141118A - 除草的水溶性的颗粒组合物 - Google Patents

除草的水溶性的颗粒组合物 Download PDF

Info

Publication number
CN1141118A
CN1141118A CN96106822A CN96106822A CN1141118A CN 1141118 A CN1141118 A CN 1141118A CN 96106822 A CN96106822 A CN 96106822A CN 96106822 A CN96106822 A CN 96106822A CN 1141118 A CN1141118 A CN 1141118A
Authority
CN
China
Prior art keywords
alkali
composition according
weed killer
composition
killer herbicide
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.)
Granted
Application number
CN96106822A
Other languages
English (en)
Other versions
CN1075930C (zh
Inventor
J·沙莫斯
M·沙夫
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of CN1141118A publication Critical patent/CN1141118A/zh
Application granted granted Critical
Publication of CN1075930C publication Critical patent/CN1075930C/zh
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/12—Powders or granules

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

本发明涉及固体水溶性颗粒组合物，它包括咪唑啉酮一种除草剂或与第二除草剂的混合物以及碱，其中较好的是碱的用量为碱与咪唑啉酮的摩尔当量比约为0.9-2.0。所述的组合物是储存稳定的，并迅速基本完全地溶于水中以便能均匀地施用于施用处的表面。

Description

除草的水溶性的颗粒组合物
本发明涉及固体水可溶的颗粒组合物。
农业配方研究正逐步转向固体组合物以增加处理的安全性和对环境的有益性。人们一直提出由装在塑料或金属容器中的溶剂型的液体浓缩液、水悬浮浓缩液和水分散性粉末或颗粒造成的健康和环境问题。
咪唑啉酮化合物是一类高效的、有益于环境、对作物有选择性的除草剂，它在相邻于咪唑啉酮环处含有吡啶或喹啉羧酸官能团。但是，已知咪唑啉酮环是不稳定的，在碱的存在下会降解。虽然已知取代的苯氧基和苯甲酸化合物的固体、水溶性的除草剂盐组合物和它们的制备方法，但所述的化合物均无碱降解敏感性方面的具体说明(美国专利5,266,533和5,328,889)。
因此，本发明的一个目的是提供基本完全水溶性且储存稳定的固体咪唑啉酮组合物。
本发明的另一个目的是提供有环境所需特性，且对农民、操作者和使用者安全方便的农用组合物。
本发明的这些目的和进一步的目的和特征将从下面的详细叙述中更为明显。
本发明提供了一种固体、水溶性的除草剂组合物，该组合物包括咪唑啉酮一种除草剂或与第二除草剂的混合物，以及碱，其中较好的是碱的用量是碱对咪唑啉酮除草剂的摩尔当量之比约0.9-2.0。所述的组合物适合包装于水溶性材料，因为是适合环境、安全的农用产品，它完全溶解就可均匀施用在所有施用处的表面。
咪唑啉酮吡啶和喹啉羧酸除草剂是两性离子化合物，其水溶性相当低。溶解度随着pH的增加而增加，因羧酸成为离子。但是，pH＞7时咪唑啉酮环是不稳定的。因此，为了增加储存的稳定性并避免产物降解，该极有价值的农用产品配方物已是为液体组合物，如非均相的悬浮浓缩液或酸性的水浓缩液，它们对冷冻敏感，需要昂贵的包装材料；或为固体组合物，如水分散颗粒或可湿性粉末，这需要麻烦的机械混合工序，得到非均相施用的产品，会有沉积、不均匀施用和可能堵塞喷洒装置的问题。
现已发现一种组合物，该组合物包括咪唑啉酮一种除草剂或与第二除草剂的混合物和碱，其中较好的是碱的用量是碱的摩尔当量与咪唑啉酮除草剂的摩尔当量的比率约为0.9-1.2，更好的约为1.1-1.7，这样的组合物能稳定储存、耐冷冻且基本完全溶于水。本发明组合物适合于环境有利的水溶性包装，它安全并易于处理，并且得到均相的施用产物，保证将有效成分均匀施用在施用处的表面。
咪唑啉酮可有一种或多种下式I化合物其中Y和Z均可为氢、卤素、任意被卤素取代的C1-C4烷基或C1-C4烷氧基，Y和Z可结合在一起表示为结构-CH＝CH-CH＝CH-。较好的咪唑啉酮除草剂是Z是氢，Y是氢、甲基、乙基或甲氧基甲基，或当Y和Z结合在一起表示为结构-CH＝CH-CH＝CH-的式I化合物；例如，2-(4-异丙基-4-甲基-5-氧基-2-咪唑啉-2-基)烟酸；2-(4-异丙基-4-甲基-5-氧基-2-咪唑啉-2-基)-5-甲基烟酸；5-乙基-2-(4-异丙基-4-甲基-5-氧基-2-咪唑啉-2-基)烟酸；2-(4-异丙基-4-甲基-5-氧基-2-咪唑啉-2-基)-3-喹啉羧酸或2-(4-异丙基-4-甲基-5-氧基-2-咪唑啉-2-基)-5-(甲氧基甲基)烟酸。
本发明的碱是加入溶液时可增加pH的任何物质。适用于本发明组合物的碱是最常见的那些，如碱金属氢氧化物，即NaOH，KOH之类，或碱金属盐，如碳酸盐或碳酸氢盐，即，Na2CO3、NaHCO3、K2CO3、KHCO3之类，磷酸盐，即Na3PO4、K3PO4等等，较好的是碳酸盐或碳酸氢盐。碱的用量可根据用作有效成分的咪唑啉酮除草剂的水溶性而定。一般来说，碱的较好用量以与咪唑啉酮除草剂的摩尔当量比率来度量，约为0.9-2.0，更好的是1.1-1.17。当然，应当明白摩尔当量比率大于2.0也可得到可溶性的组合物，但过量的碱一般是不需要的。
预期用于本发明组合物的第二除草剂是任何水溶性对除草有效化合物，如(2，4-二氯苯氧基)乙酸盐(2，4-D)、4-(2，4-二氯苯氧基)丁酸盐(2，4-DB)、2-(4-氯-2-甲基苯氧基)丙酸盐(MCPP)、4-氯-2-(甲基苯氧基)乙酸盐(MCPA)、2-(2，4-二氯苯氧基)丙酸盐(2，4-DP)、3，6-二氯-2-甲氧基苯甲酸盐(麦草畏)、3-氨基-2，5-二氯苯甲酸盐(草灭平)之类的取代苯氧基或苯甲酸盐。盐的阳离子可为任何标准的羧酸阳离子，如铵、有机铵、钠、钾等。第二除草剂的用量为0-85％(重量)。
本发明组合物也包括一般用于固体农用组合物的标准配方助剂，如染料、分散剂、惰性填料等，诸如烷基萘缩合物、木质素磺酸盐、聚环氧乙烷、聚环氧丙烷等的分散剂是适用的，较好的是烷基萘缩合物。水溶性的惰性填料较好的是诸如氯化钠、淀粉、糖之类。
本发明组合物可用标准的干压或挤出技术制备。一般来说，将干燥的组分研磨或机械混合，然后进料入压片机或压实机，或使研磨或混合的粉末湿润，挤出并干燥。然后使颗粒产品用标准技术过筛得到均匀粒径的干燥颗粒。
在实际应用中，所有的固体组分，包括较好的以约0.9-2.0，更好的是约1.1-1.7摩尔当量比率，或等当量的碱和咪唑啉酮除草剂放在Munson混合器(由Munson Machinery Company纽约，尤蒂卡，制造)或同类混合器中混合约30分钟。在混合时将约7-12％(重量)，较好的是约10％(重量)生产用水喷在混合物上，并继续搅拌15分钟。所得的潮湿混合物进料到篮式制粒机中并挤出。将挤出的产物摊在盘中，干燥。
为了更清楚地理解本发明，下面给出具体的实施例。这些实施例仅供说明用，不能用来限制本发明的范围和原理。确实，除了本发明这里所述之外，对本发明的各种修改对该技术领域人员来说是显而易见的，这类修改也在本发明的权利要求范围里。实施例1水溶性除草剂颗粒组合物的制备一般方法
将所有的固体组分混合约30分钟。在混合器操作时向混合的混合物喷洒约10％(重量)生产用水，并继续混合约15分钟。用标准的LCI公司的台式上挤出机(美国北卡罗来纳州大夏洛特)挤出潮湿的混合物，挤出物在流化床干燥器上干燥，干燥的材料过筛得到均匀粒径的颗粒。
用上述方法制备下表I的组合物，并评价其储存稳定性。
表I中所有的组合物在除草剂施用浓度的4倍的情况下是完全溶于水(0.2克颗粒组合物/99.8克水)。
从表1中可见，所有的组合物有储存稳定性。
                          表1
                                                       重量/重量％
组分                           用途         A         B         C2-(4-异丙基-4′-甲基-5-氧基-2-咪    咪唑啉酮除    72.67      72.52      72.08唑啉-2-基)-5-甲氧基甲基烟酸         草剂(98.2％工业级)Na2CO3                            碱            11.55      2.90       19.22Aerosol OTB1                       分散剂        0.61       -          -Igepon T772                        分散剂        0.61       -          -Morwet EFW3                        分散剂        -          4.84       4.81STAR-DRI4                          惰性填料      11.55      4.84       -NaCl                                惰性填料      -          11.70      -水                                  残留水份      3.00       3.20       3.90碱与除草剂的摩尔当量比                            0.932      0.234      1.56稳定性5-开始(有效成分的重量/重量％)              71.05      71.05      72.845℃下3个月后] 69.75                              70.05      72.6       1 55℃
                                                                    下1个
                                                                    月71.20                                             72.85      73.51Cytech(康涅狄格州，斯坦福)2GAF化学品公司(新泽西州，韦恩)3Witco公司(德克萨斯州，休斯敦)4A.E.Staley制造公司(伊黎诺伊州，迪凯特)5分析误差为±2％实施例2含有效成分的A混合物的水溶性除草剂颗粒组合物的制备
除了将染料溶于生产用水外，其它用实施例1所述的基本相同方法，制备下列组合物并进行评价。
  组分                          用途             重量/重量％5-乙基-2-(4-异丙基-4-甲基-5-氧  咪唑啉酮除草剂         19.92基-2-咪唑啉-2-基)烟酸(96％，工业级)麦草畏钠(78％，工业级)          第二除草剂             73.56碳酸钠                          碱                     4.00Morwet EFW1                    分散剂                 1.00FD&C Blue2 No.1                染料                   0.01氯化钠                          惰性填料               1.51碱与咪唑啉酮除草剂的摩尔当量比                         1.141Witco公司(德克萨斯州，休斯敦)2Tricon Colors公司(新泽西州，埃尔姆伍德公园)
将试验组合物(2.0克)加到在量筒中的98克水中。塞住量筒，翻转数次直至肉眼观察到完全透明的溶液。在9-13次翻转后试验组合物溶解。实施例3水溶性除草剂的颗粒组合物的制备一般方法
研磨所有的干组分，然后加入标准的台式上压片机，在约500-1500psi的压力下压制得到干燥的颗粒。
用上述方法制备如下表II所示的组合物。表II中所有的试验组合物在大于除草剂施用浓度的4倍的情况下都溶于水中。
                                   表II
                           水溶性除草剂颗粒组合物
                                                              (wt/wt％)
     组分                   用途        A     B    C    D    E    F    G    H2-(4-异丙基-4-甲基-5-氧基-  咪唑啉酮除草剂    75.51  -     -     -     -     -     -     -2-咪唑啉-2-基)烟酸2-(4-异丙基-4-甲基-5-氧基-  咪唑啉酮除草剂    -      77.96 -     -     -     -     -     -2-咪唑啉-2-基)-5-甲基烟酸5-乙基-2-(4-异丙基-4-甲基-  咪唑啉酮除草剂    -      -     70.59 71.01 69.09 -     -     -5-氧基-2-咪唑啉-2-基)烟酸2-(4-异丙基-4-甲基-5-氧基-  咪唑啉酮除草剂    -      -     -     -     -     72.53 67.29 66.452-咪唑啉-2-基)-3-喹啉羧酸K3PO4                     碱               22.45   20.01 25.49 -     -     23.52 -     -Na2CO3                    碱               -       -     -     28.40 -     -     32.07 -NaHCO3                     碱               -       -     -     -     30.30 -     -     32.89Aerosol OTB1               分散剂           0.20    2.02  0.65  0.60  0.60  0.22  0.63  0.66Morwet D-4252              分散剂           -       -     1.31  -     -     -     -     -纤维素胶                    惰性填料         0.82    -     -     -     -     -     -     -STAR-DRI3                                                                   1.76MYVAPLEX 6004           惰性填料         1.02    -     -     -     -     1.96  -     -碱与咪唑啉酮除草剂的摩尔当量比               1.1     1.0   1.5   2.2   1.5   1.4   2.8   1.81Cytech公司(康涅狄格州，斯坦福)2Witco公司(德克萨斯州，休斯敦)3A.E.Staley制造公司(伊黎诺伊州，迪凯特)4Eastman化学公司(田纳西州，金斯波特)

Claims (10)

1.一种除草的、水溶的、固体颗粒组合物，包括咪唑啉酮一种除草剂或咪唑啉酮除草剂与第二除草剂的混合物，以及碱。
2.根据权利要求1所述的组合物，其中碱的用量为碱与咪唑啉酮除草剂的摩尔当量比率约为0.9-2.0。
3.根据权利要求1所述的组合物，其中咪唑啉酮除草剂具有下式I结构：其中Y和Z均可为氢、卤素、任意被卤素取代的C1-C4烷基或C1-C4烷氧基，Y和Z可结合在一起表示为结构-CH＝CH-CH＝CH-。
4.根据权利要求1所述的组合物，其中第二除草剂是固体的取代的苯甲酸盐或固体的取代的苯氧基羧酸盐，其用量约为0-85％(重量)。
5.根据权利要求1所述的组合物，其中碱是碱金属氢氧化物、碱金属碳酸盐或碱金属磷酸盐。
6.根据权利要求2所述的组合物，它有式I除草剂，其中X是氢；Y是氢、甲基、乙基或甲氧基甲基；或Y和Z可结合在一起表示为-CH＝CH-CH＝CH-。
7.根据权利要求3所述的组合物，其中第二除草剂使麦草畏的钠盐。
8.根据权利要求6所述的组合物，其中碱的用量为碱与咪唑啉酮除草剂的摩尔当量比率约为1.1-1.8。
9.根据权利要求7所述的组合物，其中咪唑啉酮除草剂是5-乙基-2-(4-异丙基-4-甲基-5-氧基-2-咪唑啉-2-基)烟酸。
10.根据权利要求9所述的组合物，其中碱是碳酸钠。
CN96106822A 1995-06-06 1996-06-06 除草的水溶性的颗粒组合物 Expired - Fee Related CN1075930C (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/466,654 US5696024A (en) 1995-06-06 1995-06-06 Herbicidal water soluble granular compositions
US466,654 1995-06-06
US466654 1999-12-20

Publications (2)

Publication Number Publication Date
CN1141118A true CN1141118A (zh) 1997-01-29
CN1075930C CN1075930C (zh) 2001-12-12

Family

ID=23852600

Family Applications (1)

Application Number Title Priority Date Filing Date
CN96106822A Expired - Fee Related CN1075930C (zh) 1995-06-06 1996-06-06 除草的水溶性的颗粒组合物

Country Status (25)

Country Link
US (1) US5696024A (zh)
EP (1) EP0749688B1 (zh)
JP (1) JP3856349B2 (zh)
KR (1) KR970000033A (zh)
CN (1) CN1075930C (zh)
AR (1) AR002340A1 (zh)
AT (1) ATE195628T1 (zh)
AU (1) AU718758B2 (zh)
BR (1) BR9602620A (zh)
CA (1) CA2178163C (zh)
CZ (1) CZ291032B6 (zh)
DE (1) DE69609904T2 (zh)
DK (1) DK0749688T3 (zh)
ES (1) ES2150074T3 (zh)
GR (1) GR3034476T3 (zh)
HR (1) HRP960273B1 (zh)
HU (1) HU216153B (zh)
IL (1) IL118504A (zh)
PT (1) PT749688E (zh)
RU (1) RU2152151C1 (zh)
SK (1) SK283508B6 (zh)
TR (1) TR199601041A1 (zh)
TW (1) TW314449B (zh)
UA (1) UA46721C2 (zh)
ZA (1) ZA964678B (zh)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111970927A (zh) * 2018-04-13 2020-11-20 拜耳公司 包含碳酸亚丙酯的杀虫混合物制剂

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6043195A (en) * 1998-03-03 2000-03-28 American Cyanamid Company Method for the enhancement of seedhead suppression in turf
DE19815820A1 (de) * 1998-04-08 1999-10-14 Hoechst Schering Agrevo Gmbh Synergistische herbizide Mittel auf Basis von phosphorhaltigen Blattherbiziden, Imidazolinonen und Wuchsstoffherbiziden
US5981434A (en) * 1998-06-04 1999-11-09 Kaplan; Jeff Herbicidal composition for the control of epiphytic weeds
EP1267621B1 (en) * 2000-03-27 2004-02-11 Basf Aktiengesellschaft Synergistic herbicidal methods and compositions
EP1432307B1 (en) * 2001-09-26 2007-09-19 Platte Chemical Company Herbicide microemulsion-forming concentrates, microemulsions, and methods
AR041211A1 (es) * 2002-09-12 2005-05-11 Du Pont Procedimiento para preparar composiciones de sulfonamida extruidas en pasta
US20040121026A1 (en) * 2002-12-23 2004-06-24 Kaplan Jeffrey Lee Non-toxic composition for the control of epiphytic weeds
ES2213483B1 (es) * 2003-02-10 2005-12-01 Laboratorios Agrochem, S.L. Procedimiento de transformacion del imazalil en un producto granular.
CA2563261C (en) 2004-04-14 2013-04-09 Fmc Corporation Dispersible pesticidal compositions
TWI556742B (zh) * 2014-07-21 2016-11-11 Chin I Chen A herbicidal composition
CN111466374A (zh) * 2020-05-11 2020-07-31 赵邦斌 一种农药可溶性粒剂及其制备方法

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5334576A (en) * 1986-07-28 1994-08-02 American Cyanamid Company 5 (and/or 6) substituted 2-(2-imidazolin-2-yl)nicotinic acids, esters and salts, useful as herbicidal agents and novel intermediates for the preparation of said nicotinic acids, esters and salts
US4816060A (en) * 1986-08-15 1989-03-28 American Cyanamid Company Herbicidal aqueous compositions of imidazolinone herbicides
US5256625A (en) * 1987-08-13 1993-10-26 Monsanto Company Safening imidazolinone herbicides
EP0454968A1 (en) * 1990-04-30 1991-11-06 American Cyanamid Company Method for enhancing the biological activity of formulations containing solid imidazolinyl benzoic acid esters
ES2151879T3 (es) * 1990-12-21 2001-01-16 Aventis Cropscience Gmbh Mezclas de herbicidas y antidotos.
US5328889A (en) * 1992-07-10 1994-07-12 Pbi-Gordon Corporation Dry, water-soluble, substituted phenoxy and/or benzoic acid herbicides and method of preparing same
US5221319A (en) * 1991-08-16 1993-06-22 Pbi-Gordon Corporation Dry, water-soluble, substituted phenoxy and/or benzoic acid herbicidal compositions and method of preparing same
CA2115760C (en) * 1991-08-16 1998-07-14 John L. Van Haften Dry, water-soluble, substituted phenoxy and/or benzoic acid herbicides and method of preparing same
US5280008A (en) * 1991-08-16 1994-01-18 Pbi-Gordon Corporation Dry, water-soluble powder, substituted heterocyclic acid or substituted phenol herbicidal compositions, and method of preparing same
US5266553A (en) * 1991-10-21 1993-11-30 Riverdale Chemical Company Method of manufacturing a dry water-soluble herbicidal salt composition
DE59309481D1 (de) * 1992-05-15 1999-05-06 Hoechst Schering Agrevo Gmbh Synergistisch wirksame Herbizidkombinationen
DE4224929A1 (de) * 1992-07-28 1994-02-03 Bayer Ag Heterocyclyltriazolinone
US5393731A (en) * 1992-12-23 1995-02-28 American Cyanamid Company Water dispersible granular herbicidal compositions comprising dinitroaniline and imidazolinone herbicides with montmorillonite carriers
EP0623281A1 (en) * 1993-04-28 1994-11-09 American Cyanamid Company Herbicidal extruded granular compositions

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111970927A (zh) * 2018-04-13 2020-11-20 拜耳公司 包含碳酸亚丙酯的杀虫混合物制剂

Also Published As

Publication number Publication date
TR199601041A1 (tr) 1996-12-21
EP0749688A2 (en) 1996-12-27
CA2178163A1 (en) 1996-12-07
CN1075930C (zh) 2001-12-12
AU5476696A (en) 1996-12-19
DK0749688T3 (da) 2000-11-13
AR002340A1 (es) 1998-03-11
DE69609904T2 (de) 2000-12-21
HRP960273A2 (en) 1998-04-30
EP0749688B1 (en) 2000-08-23
IL118504A (en) 2000-06-29
AU718758B2 (en) 2000-04-20
EP0749688A3 (en) 1998-07-01
JP3856349B2 (ja) 2006-12-13
KR970000033A (ko) 1997-01-21
DE69609904D1 (de) 2000-09-28
ZA964678B (en) 1997-12-05
SK283508B6 (sk) 2003-08-05
ES2150074T3 (es) 2000-11-16
RU2152151C1 (ru) 2000-07-10
HUP9601533A2 (en) 1997-05-28
HRP960273B1 (en) 2001-08-31
ATE195628T1 (de) 2000-09-15
SK72296A3 (en) 1997-01-08
UA46721C2 (uk) 2002-06-17
TW314449B (zh) 1997-09-01
HU9601533D0 (en) 1996-07-29
CA2178163C (en) 2008-02-12
US5696024A (en) 1997-12-09
CZ291032B6 (cs) 2002-12-11
JPH08337505A (ja) 1996-12-24
HU216153B (hu) 1999-04-28
PT749688E (pt) 2001-01-31
HUP9601533A3 (en) 1997-08-28
CZ157196A3 (en) 1996-12-11
IL118504A0 (en) 1996-09-12
BR9602620A (pt) 1998-04-22
GR3034476T3 (en) 2000-12-29

Similar Documents

Publication Publication Date Title
CN1075930C (zh) 除草的水溶性的颗粒组合物
JP4408630B2 (ja) 濃縮された水溶性顆粒状植物成長調節剤配合物およびそれらの使用方法
CA2047755C (en) Pelletizing phosphoroamidothioate derivatives with fertilizers and other pesticides
KR100266459B1 (ko) 농약 마이크로캡슐 및 이의 제조방법
CN112512319A (zh) 农业化学组合物
NL9002765A (nl) Dispergeerbare korrels van fungicide produkten.
AU679773B2 (en) High concentrated, solid mepiquat chloride and chlormequat chloride products
CN102067842B (zh) 稻田除草剂组合物
US5883047A (en) Granules of hygroscopic, water-soluble products
CN104284582B (zh) 除草剂组合物及其工艺
JPH08505368A (ja) 粒状の水溶性または吸湿性の農業用配合物およびその製造法
EP0757519B1 (en) Highly concentrated, solid acifluorfen powders and processes for making dry form solid acifluorfen powders
CA2160158C (en) Solid crop protection formulation
CN1230342A (zh) 酰苯胺与磺酰脲类除草剂组合物

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C14 Grant of patent or utility model
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20011212

Termination date: 20150606

EXPY Termination of patent right or utility model