CN1069813C - 1-{[邻-(环丙基羰基)-苯基]-氨磺酰}-3-(4,6-二甲氧基-2-嘧啶基)脲除草剂 - Google Patents
1-{[邻-(环丙基羰基)-苯基]-氨磺酰}-3-(4,6-二甲氧基-2-嘧啶基)脲除草剂 Download PDFInfo
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Abstract
本发明涉及一种作物选择性除草剂1-{[邻-(环丙基羰基)苯基]-氨磺酰}-3-(4,6-二甲氧基-2-嘧啶基)脲,及其制备方法和用所述的选择性作物的氨磺酰脲衍生物选择性地控制存在于作物中的不合乎需要的植物品种的方法。
Description
本申请为发明专利申请CN91101025.4的分案申请。
美国专利No.4,622,065、4,666,508、4,696,695和4,741,762公开了氨磺酰脲衍生物。这些专利文献中,证明所公开的氨磺酰脲衍生物有除草活性,但并未提供在谷物存在下显示选择性地控制野草的证据。
本发明的目的为提供一种1-{[邻-(环丙基羰基)-苯基]-氨磺酰)-3-(4,6-二烷氧基-2-嘧啶基)脲衍生物,用作选择性控制在作物中有害植物种类的高效除草剂。
同时,本发明的目的为提供一种1-{[邻-(环丙基羰基)-苯基]-氨磺酰)-3-(4,6-二烷氧基-2-嘧啶基)脲衍生物作物选择性除草剂,当施用于阔叶杂草和生长在谷物诸如:大麦、小麦、燕麦、黑麦、旱(陆)稻中的草显示至少2的安全系数,而当用于控制存在于移植水稻中的阔叶杂草和莎草时显示至少4的安全系数。
另外,本发明的目的为提供一种用1-{[邻-(环丙基羰基)-苯基]-氨磺酰)-3-(4,6-二烷氧基-2-嘧啶基)脲选择性控制存在于谷物中的有害植物的方法。通过上述氨磺酰脲除掉的所控制的有害杂草种类包括:钝叶决明;年莎草,莎草科的Cyperaceae annual;黄莎草,莎草属的Cyperus esculentus;莎草,莎草属的Cyperus serotinus;慈菇Saqittaria pyqmaea;紫莎草,莎草;珍珠稗,藨草属的Scirpus spp;牵牛花,番薯属的Ipomoea spp.以及***,田菁属的Sesbaniaexaita。
本发明涉及制备1-{[邻-(环丙基羰基)-苯基]-氨磺酰)-3-(4,6-二甲氧基-2-嘧啶基)脲的方法以及选择性控制存在于作物中有害植物种类的方法。业已发现上述化合物对存在于谷物作物中的杂草品种的选择性控制是有效的,以及用于控制存在于移植的或水稻中的阔叶杂草和莎草尤其有效。
另外,业已发现1-{[邻-(环丙基羰基)-苯基]-氨磺酰)-3-(4,6-二甲氧基-2-嘧啶基)脲在氨磺酰脲衍生物中在优异的安全系数上对谷物是独特的。
根据本发明1-{[邻-(环丙基羰基)-苯基]-氨磺酰)-3-(4,6-二甲氧基-2-嘧啶基)脲可通过2-氨基-4,6-二甲氧基-2-嘧啶与氯异氰酰磺酰酯在二氯甲烷存在下反应接着将由此制备的反应混合物用邻-氨基苯基环丙基酮和三乙胺在二氯甲烷的存在下处理,以得到所需的化合物。
在谷物中尤其在稻子中的选择性的发现,是由于环丙基上的羰基官能团连结至氨磺酰脲衍生物的苯环上被意外地获得的。另外,发现该取代基团同时提供选择性控制存在于大麦、小麦、燕麦、黑麦以及稻子中各种有害杂草,尤其是阔叶杂草和莎草,是优异的。附加地,它的最大优点,发现对几种有害杂草,诸如:稗和鹅观草的生长和成熟,如果它们未被杀灭,当这类杂草与1-{[邻-(环丙基羰基)-苯基]-氨磺酰)-3-(4,6-二甲氧基-2-嘧啶基)脲在谷物处理期间控制存在于谷物作物中的阔叶杂草和莎草时被分别地抑制。
实际上,上述氨磺酰脲对谷物可以以固体或液体的除草剂组合物形式施用,它包括氨磺酰脲的除草的有效数量分散于惰性固体或液体的载体中。该配方可用作耕作前和发芽后处理。然而,对稻子处理,通常地最有效用上述配方较佳地为颗粒配方,作为移植后发芽前处理,即:在稻子移植后施用于土壤或田水中,但在杂草发生前或很短时间后。
同时该配方也可以施用于种植前结合着处理。同时,上述配方也可以在杂草已经发生后对谷物作物作叶簇施用,涂在叶上特别适用于控制在大麦、小麦、燕麦、黑麦和直接播种的稻子中的杂草。
1-{[邻-(环丙基羰基)-苯基]-氨磺酰)-3-(4,6-二甲氧基-2-嘧啶基)脲可以配制成可湿性粉剂,可流动液体或颗粒配方施用于作物对控制的杂草是有利的。
可湿性粉剂可通过约65%W/W的1-{[邻-(环丙基羰基)-苯基]-氨磺酰)-3-(4,6-二甲氧基-2-嘧啶基)脲、25.70%W/W的膨润土、6.0%W/W无糖的改性木质素磺酸钠(分散剂)、3.0%W/W的阴离子表面活性剂诸如:二辛基硫代琥珀酸钠(润湿剂)、0.20%W/W的二氧化硅和0.10%W/W的硅氧烷去泡剂一起研磨制备。
作为这种可湿性粉剂的应用于在谷物和在谷物中生长的杂草,通常将该可湿性粉剂分散在水中并以液体喷洒施用。一般地,施用的喷洒的足够的数量为提供约0.016至1.0千克/公顷以及较佳地为0.02至0.20千克/公顷的上述1-{[邻-(环丙基羰基)-苯基]-氨磺酰)-3-(4,6-二甲氧基-2-嘧啶基)脲足以选择性地控制存在于谷物作物中的有害植物,尤其是阔叶杂草和莎草。
上述氨磺酰脲衍生物也可以制备成一种颗粒配方通过溶解或分散该活性化合物在诸如:丙酮、二氯甲烷或诸如此类的溶剂中并用该毒物溶剂混合物在吸着性颗粒中,诸如:凹凸棒石(镁山软木),蒙脱石、金刚石砂粒、膨润土以及诸如此类中。通常地,在施用的颗粒的充足的毒物溶液保证在颗粒中提供自约0.20%W/V至约2.0%W/V毒物。当然,如果需要,可以制备在颗粒中更高毒物的浓度。颗粒的吸着性是使用的主要限制因素。通常地,颗粒施用于作物生长的土壤或水中,以保证约0.016至1.0千克/公顷和较佳地为0.02至0.20千克/公顷毒物对处理作物面积的足够的数量。
一种典型的可流动浓缩物配方可通过约20%至60%重量的氨磺酰脲、1%至5%重量的缩合的萘磺酸钠盐、2%至4%重量的凝胶陶土、2%重量的丙二醇和约30%至55%重量的水一起研磨制备。
可流动浓缩物通常地分散于水中,施用于谷物区域以提供处理的区域为约0.016千克/公顷至1.0千克/公顷以及较佳地约0.02千克/公顷至约0.20千克/公顷的充足的数量。
以下将通过实施例对本发明作进一步的说明。
实施例1:邻-氨基苯基环丙基酮的制备
向100毫升1.0MBCl3在二氯甲烷的溶液和100毫升二氯乙烷于0-5℃加入9.3克(0.1摩尔)苯胺、随着苯胺的加入向混合物加入10.0克(0.15摩尔)环丙腈以及其后分批向其中加入14.4克(0.11摩尔)AlCl3。将混合物温热至室温并放置蒸馏装置。通过蒸馏从混合物中蒸去二氯甲烷直至釜温达到70℃。残留的混合物回流过夜(18小时)。
将反应混合物于冰浴中冷却并将水加入到冷却的混合物中。加入足够的水以溶解在混合物中的固体以及然后用100毫升二氯甲烷将全部混合物萃取二次。合并有机萃取液,在无水MgSO4上干燥以及在真空中蒸发得到9.3克黄色油,(70%纯产物)通过NMR分析。
该反应由下式所示:
实施例2:1-{[邻-(环丙基羰基)-苯基]-氨磺酰)-3-(4,6-二甲氧基-2-嘧啶基)脲的制备
将1.78克(0.0114摩尔)2-氨基-4,6-二甲氧基嘧啶在50毫升二氯甲烷的溶液在冰浴中冷却至0.5℃,然后将1.0毫升(1.62克,0.114摩尔)氯异氰酸磺酸酯加入至该溶液。将产生的混合物搅拌30分钟以及将2.66克邻-氨基苯基环丙基酮(70%纯,0.0114摩尔)和2.6毫升三乙胺(0.0187摩尔)在50毫升二氯甲烷的溶液缓慢地加至该混合物中、产生的溶液于环境温度下搅拌过夜(18小时)。
然后将反应混合物于真空中蒸发并将产生的残留物溶解在50毫升甲醇中。用10%HCl将产生的溶液的pH调节至1并将该溶液静置。在溶液中形成白色固体沉淀,过滤和干燥,得到3.8克(70%)的所需的产物,熔点170°-171℃。该反应可由下式所示:
实施例3:在旱地条件下芽前稻子的允许剂量:
对本发明的例示的化合物芽前稻子的允许剂量由以下试验测定:稻种(CVTebonnet)播种在巴氏蒸汽清毒的具有1.5%有机物质的黄樟木砂填实的土壤的三只4英寸见方的塑料盆中。播种后,该盆浇水至田间含水量以及然后用实验室环状喷洒器喷洒。试验化合物为液体丙酮50/V/V的混合物以相当于1.0、0.5、0.25、0.125、0.063、0.032、0.016和0.008千克/公顷的比例施用。然后,将试验的盆子置于暖房分期浇水并按通常的暖房条件看管。3至4周后处理每一被测试的容器以目测标准为基础,从大小、活力、失绿、生长畸形以及所有植物外观额定除草效率。其结果采用如下的评定体系:级别 意义 控制%(对照检查)
0 无效果 0
1 微量效果 1-5
2 稍有效果 6-15
3 中等效果 16-29
4 杀伤 30-44
5 明显的杀伤 45-64
6 除草效果 65-79
7 良好的除草效果 80-90
8 接近完全杀死 91-99
9 完全杀死 100
在实施例中报导的结果采用以下的略语:
略语 相当于
PE 芽前
PoST-T 移植后
BYG 稗
CYPSE 慈菇
G/HA 克/公顷
KG/HA 千克/公顷
试验结果在以下报导:水稻选择性(芽前)
化合物 比例 除草级别1-{[邻-(环丙基羰基)- 1.00 7苯基]-氨磺酰)-3- 0.50 7(4,6-二甲氧基-2-嘧 0.25 5啶基)脲 0.125 1
0.063 0
0.032 0
0.016 0
0.008 0
在水田条件下对移植后施用的稻子的允许剂量:
移植的稻子的允许剂量在移植后除草剂施用的测定如下:将二种10日令的稻禾(CV.Tebonnet)移植在粉砂沃土壤的具有直径10.5cm和无排水孔的32盎司的塑料容器中。移植后,该容器浸入以及水平面保持在土壤表面上1.5至3厘米。移植3天后,容器的浸过水的土壤表面用选定的液体/丙酮50/50V/V含有试验化合物的混合物处理以提供相当于1.0、0.5、0.25、0.125、0.063、0.032、0.016和0.008千克/公顷的活性成份。将处理过的容器置于暖房种植台上,将水浇到保持上述的水平,并按正常的暖房流程照管。处理3-4周后结束试验并测定每一容器,而除草效果按照上述评级***评级。
水田条件—移植后施用
化合物 千克/公顷 BYG CYPSE RICE1-{[邻-(环丙基羰基) 1.00 9 9 3苯基]-氨磺酰)-13 0.50 9 9 1-(4,6-二甲氧基-2-嘧 0.125 9 9 0啶基)脲 0.063 8 9 0
0.032 8 8 0
0.016 5 8 0
0.008 2 - 0
在水田条件下芽前杂草的控制:
在水田条件下对稗和慈菇的萌前除草活性的测定如下:将稗子或慈菇块茎种植在高5厘米的在32盎司的直径为10.5厘米和无排水孔的塑料容器的粉砂沃土中。将水加入至该容器并在试验期间保持在土壤表面1.5至3厘米上。试验化合物用液体/丙酮50/50V/V的混合物直接地滴入灌溉水中以得到排当于1.0、0.5、0.25、0.125、0.063、0.032、0.016和0.008千克/公顷的活性成分。将试验容器置于暖房种植台上并按正常暖房过程照管。3至4个星期后结束试验并测试每一容器,并按上述等级***定级除草效果。
对稻安全的比例和杂草控制的比例
对稻安全的比例为稻子除草等级0或1的最高比例(克/公顷)。对杂草控制的比例为除草等级8或9的最低比例(克/公顷)。
对稻安全比例 控制稗 控制慈菇
(芽前)(芽后) 比例 比例
化合物 —克/公顷—1-{[邻-(环丙基羰基)- 63 500 32 16苯基]-氨磺酰)-3-(4,6-二烷氧基-2-嘧啶基)脲选择性系数
选择性系数为稻子的安全的比例(克/公顷)除以每一种类的(稗和慈菇杂草控制的比例(克/公顷)。用移植的稻子的安全的比例和对萌前稻子的安全的比例计算。虽然萌前稻子播种方法是不采用灌溉水田的条件,但从生理学上对稻子的这些除草剂的允许剂量的评价是一个十分接近的方法。(当播种的稻子自种子发芽期间至暴露于除草剂时)。
选择性系数
稻移植后 稻子芽前
化合物 稗 慈菇 稗 慈菇1-{[邻-(环丙基羰基)- 16 32 2.0 4苯基]-氨磺酰)-3-(4,6-二甲氧基-2-嘧啶基)脲实施例4:阔叶杂草的杂草控制和对小麦和大麦芽后的允许剂量:
萌后的除草活性以及小麦和大麦的优择性通过以下试验说明。将每一植物种类的种子或繁殖器官分别种植于商业上的人工暖房生长介质包括:泥炭、蛭石、砂和木炭的(Metromix 350)杯中。将植物在暖房中生长约2周。然后该植物用含有试验化合物的足以提供相当于约0.004至2.0千克/公顷的选定的液体丙酮溶液喷洒。这些溶液同时含有约2摩尔当量二乙胺/每当量的试验化合物,以增加试验化合物在液体丙酮溶液中的溶解度。这些溶液还含有0.25%的诸如:烷基芳基聚氧乙烯乙二醇加上游离脂肪酸和异丙醇的喷洒活性剂。
喷洒后,将植物置于暖房试验长台上并以通常的方法经传统的暖房实际进行照管处理3-4周后测定每一杯子,并按前面实施例中报导的级别***评定除草效果。
对于谷类的允许剂量,被处理的三盆的每一个试验由三盆的平均值得出的数据表示。
采用在这些试验中的作物和杂草品种:
谷物普通名称和品种 科学名称稻CV,Tebonnet Oryza sativa冬大麦CV.Barberouse Hordeum Vulqare春大麦CV.Bonanza Hordeum vulqare冬小麦CV.Fidel Triticum aestivum春小麦CV.Katepwa Triticum aestivum硬质小麦CV.Wakooma Triticum aestivum
杂草品种略称 普通名称 科学名称BYG 稗 Echinochloa crus-qalliCYPSE 莎草 Cyperus serotinusGALAP 猪殃殃 Galium aparineSTEME 繁缕 Stellaria mediaTAROF 蒲公英 Taraxacum officinaleKCHSC 地肤 Kochia scopariaVIOAR 田堇菜 Viola arvensisPAPSS 罂粟 Papaver sp.MATIN 臭甘菊 Matricaria inodoraPRUVS 夏枯草 Prunella vulqarisVERSS 婆婆纳 Veronica sp.
施用1-{[邻-(环丙基羰基)-苯基]-氨磺酰)-3-(4,6-二甲氧基-2-嘧啶基)脲对芽后的谷物种类和各种允许剂量。
根据上述的等级***观察到的除草等级:
冬大麦 冬小麦 硬质小麦 春小麦 春大麦千克/公顷2.00 5.3 3.7 3.7 4.0 5.31.00 4.0 2.7 3.0 2.3 4.30.500 3.7 2.7 2.3 2.0 4.00.250 2.3 1.7 0.7 1.7 3.70.125 1.7 1.0 0.0 1.3 2.70.063 0.7 0.0 0.3 0.0 1.30.032 0.3 0.0 0.0 0.0 0.3
用实施例3的等级***,评定施用1-{[邻
-(环丙基羰基)-苯基]-氨磺酰)-3-(4,6-
二甲氧基-2-嘧啶基)脲对萌后杂草种类的控制
杂草种类
比例千克/公顷 猪殃殃 繁缕蒲 公英 地肤 田堇菜 罂粟 臭甘菊 夏枯草 婆婆纳0.125 9 0 9 4 0 6 9 9 90.063 9 0 9 3 0 8 8 9 70.032 9 0 5 0 0 6 9 9 30.016 8 0 4 0 0 6 9 9 30.008 7 0 4 0 0 4 7 9 00.004 4 0 0 0 0 2 5 8 0
Claims (7)
1.一种除草剂组合物,其特征在于包括有效数量的1-{[邻-(环丙基羰基)苯基]-氨磺酰}-3-(4,6-二甲氧基-2-嘧啶基)脲和惰性载体。
2.如权利要求1所述的除草剂组合物在选择性控制存在于谷物作物中有害植物上的应用方法,其特征在于对所述作物和生长在其中的有害植物的叶和茎或者对含所述有害植物种子或其它繁殖部分的生长所述作物的土壤或水施以含一定数量化合物1-{[邻-(环丙基羰基)-苯基]-氨磺酰}-3-(4,6-二甲氧基-2-嘧啶基)脲的除草剂组合物,以有效地选择性控制生长在所述作物中的所述的有害植物。
3.如权利要求2所述的方法,其特征在于所述的有害植物为稗、阔叶杂草和莎草类以及所述的作物为大麦、小麦、燕麦、黑麦和水稻。
4.如权利要求2所述的方法,其特征在于施用于所述作物和有害植物或者含所述有害植物种子或其它繁殖部分的土壤或水的化合物的施用剂量在0.016公斤/公顷至1.0公斤/公顷的1-{[邻-(环丙基羰基)苯基]氨磺酰}-3-(4,6-二甲氧基-2-嘧啶基)脲。
6.如权利要求5所述的方法,其特征在于所述的有害植物为稗、阔叶杂草或莎草类以及除草有效化合物对作物的叶子或其生长的土壤或水的施用剂量为0.016千克/公顷至1.0千克/公顷。
7.如权利要求6所述的方法,其特征在于所述作物为移植的水稻以及向其施用的化合物的剂量为0.02至0.20千克/公顷。
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US07/542,564 US5009699A (en) | 1990-06-22 | 1990-06-22 | 1-{[O-(cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dimethoxy-2-pyrimidinyl)urea herbicidal composition and use |
US07/542,564 | 1990-06-22 |
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CN91101025A Division CN1033452C (zh) | 1990-06-22 | 1991-02-09 | 1-{[邻-(环丙基羰基)-苯基]-氨磺酰}-3-(4,6-二甲氧基-2-嘧啶基)脲的制备方法 |
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CN1108880A CN1108880A (zh) | 1995-09-27 |
CN1069813C true CN1069813C (zh) | 2001-08-22 |
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CN95100195A Expired - Lifetime CN1069813C (zh) | 1990-06-22 | 1995-02-07 | 1-{[邻-(环丙基羰基)-苯基]-氨磺酰}-3-(4,6-二甲氧基-2-嘧啶基)脲除草剂 |
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US (1) | US5009699A (zh) |
EP (1) | EP0463287B1 (zh) |
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Families Citing this family (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5280007A (en) * | 1991-12-18 | 1994-01-18 | American Cyanamid Company | Method for safening rice against the phytotoxic effects of a sulfamoyl urea herbicide |
DE69303996T2 (de) * | 1992-07-06 | 1997-02-27 | American Cyanamid Co | o-Nitrophenyl Cyclopropyl Keton, herbizides Zwischenprodukt und Verfahren zu seiner Herstellung |
US5281726A (en) * | 1992-12-29 | 1994-01-25 | American Cyanamid Company | 4-hydroxy-2'-nitrobutyrophenone and tetrahydro-2-(o-nitrophenyl)-2-furanol useful as intermediates in the preparation of a crop-selective herbicide |
US5523276A (en) * | 1993-08-16 | 1996-06-04 | American Cyanamid Company | Stable herbicidal combination compositions |
CO4340715A1 (es) * | 1993-08-16 | 1996-07-30 | Basf Agrochemical Products Bv | Composiciones estables de los herbicidas sulfamoil-urea, combinados con otros herbicidas liquidos o de bajo punto de fusion |
DE4337847A1 (de) * | 1993-11-05 | 1995-05-11 | Bayer Ag | Substituierte Phenylaminosulfonylharnstoffe |
CH687746A5 (de) * | 1993-11-25 | 1997-02-14 | Mungo Befestigungstech Ag | Werkzeug zum Einbringen eines mit Aussengewinde versehenen Befestigungselementes in Baumaterial. |
CZ289916B6 (cs) * | 1993-11-30 | 2002-04-17 | American Cyanamid Company | Způsob výroby o-aminofenylketonů |
US5405998A (en) * | 1993-11-30 | 1995-04-11 | American Cyanamid Company | Process for the manufacture of cycloalkyl and haloalkyl o-aminophenyl ketones |
US5362911A (en) * | 1993-12-30 | 1994-11-08 | American Cyanamid Company | Process for the preparation of o-aminophenyl cyclo-propyl ketone |
US5380911A (en) * | 1993-12-02 | 1995-01-10 | American Cyanamid Company | Process for the manufacture of cyclopropylnitrile |
US5464808A (en) * | 1993-12-28 | 1995-11-07 | American Cyanamid Company | 1-[α-cyclopropyl-α-(substituted oxy)-o-tolyl]sulfamoyl]-3-(4,6-dimethoxy-2-pyrimidinyl)urea herbicidal agents |
DE4414476A1 (de) * | 1994-04-26 | 1995-11-02 | Bayer Ag | Substituierte Cyclopropylcarbonyl-phenylaminosulfonyl-harnstoffe |
US5492884A (en) * | 1994-04-29 | 1996-02-20 | American Cyanamid Company | 1-[2-(cyclopropylcarbonyl)-4-fluorophenyl]sulfamoyl)-3-(4,6-dimethoxy-2-pyrimidinyl) urea and its herbicidal method of use |
US5414136A (en) * | 1994-04-29 | 1995-05-09 | American Cyanamid | Method for the preparation of 4-halo-2'-nitrobutyrophenone compounds |
CZ287105B6 (en) * | 1995-06-06 | 2000-09-13 | American Cyanamid Co | Process for preparing l-{[2-(cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dialkoxy-2-pyrimidinyl)urea and intermediates for such preparation process |
US5847140A (en) * | 1995-06-06 | 1998-12-08 | American Cyanamid Company | Intermediates for the manufacture of herbicidal 1-{ 2-(cyclopropylcarbonyl) Phenyl! Sulfamoyl}-3-(4,6-dialkoxy-2-pyrimidinyl) urea compounds |
US5559234A (en) * | 1995-06-06 | 1996-09-24 | American Cyanamid Company | Process for the manufacture of herbicidal 1-{[2-(cyclopropylcarbonyl)phyenyl]sulfamoyl}-3-(4,6-dialkoxy-2-pyrimidinyl)urea compounds |
DE19530768A1 (de) * | 1995-08-22 | 1997-02-27 | Bayer Ag | Salze von N-(2-Cyclopropylcarbonyl-phenylaminosulfonyl)-N'-(4,6-dimethoxy-2-pyrimidinyl) -harnstoff |
MY116568A (en) * | 1995-10-13 | 2004-02-28 | Syngenta Participations Ag | Herbicidal synergistic composition, and method controlling weeds |
AU719770B2 (en) * | 1995-11-23 | 2000-05-18 | Syngenta Participations Ag | Herbicidal composition |
WO1998013361A1 (en) * | 1996-09-26 | 1998-04-02 | Novartis Ag | Herbicidal composition |
US7071146B1 (en) | 1996-11-11 | 2006-07-04 | Syngenta Crop Protection, Inc. | Herbicidal composition |
HRP970613B1 (en) * | 1996-12-20 | 2002-06-30 | American Cyanamid Co | Aminophenyl ketone derivatives and a method for the preparation thereof |
US6127576A (en) * | 1996-12-20 | 2000-10-03 | American Cyanamid Company | Aminophenyl ketone derivatives and a method for the preparation thereof |
US5856576A (en) * | 1997-02-04 | 1999-01-05 | American Cyanamid Company | Aryne intermediates and a process for the preparation thereof |
US6114283A (en) * | 1998-07-28 | 2000-09-05 | E. I. Du Pont De Nemours And Company | Herbicidal mixtures |
EP2052606A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
DE102008037620A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Crop Science Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
US20100092928A1 (en) * | 2008-09-19 | 2010-04-15 | Mira Stulberg-Halpert | System and method for teaching |
EA025009B1 (ru) | 2010-10-15 | 2016-11-30 | Байер Интеллектуэль Проперти Гмбх | Применение als ингибиторных гербицидов для контроля нежелательной вегетации в растениях beta vulgaris, толерантных к als ингибиторным гербицидам |
CA2834965C (en) | 2011-05-04 | 2019-08-20 | Bayer Intellectual Property Gmbh | Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant brassica, such as b. napus, plants |
ES2687545T5 (es) | 2012-12-13 | 2022-08-31 | Bayer Cropscience Ag | Uso de herbicidas inhibidores de ALS para el control de vegetación indeseada en plantas Beta vulgaris tolerantes a herbicidas inhibidores de ALS |
CN103288749A (zh) * | 2013-03-04 | 2013-09-11 | 盐城工学院 | 可作除草剂的氨基磺酰脲类化合物 |
US10413924B2 (en) * | 2013-07-19 | 2019-09-17 | Graco Minnesota Inc. | Proportioning cylinder for spray system |
KR102151974B1 (ko) | 2020-03-16 | 2020-09-07 | 주식회사 이디엔 | 무신호등 횡단보도 보행자 알림장치 |
AR127377A1 (es) | 2021-10-15 | 2024-01-17 | Kws Saat Se & Co Kgaa | Mutantes de beta vulgaris tolerantes a herbicidas inhibidores de als |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5813962A (ja) * | 1981-07-17 | 1983-01-26 | 株式会社デンソー | 自動車用冷凍サイクル制御装置 |
GB2113217A (en) * | 1982-01-12 | 1983-08-03 | Ciba Geigy Ag | Triaza compounds |
EP0184122A2 (en) * | 1984-12-03 | 1986-06-11 | Ppg Industries, Inc. | Sulfamoyl urea derivatives |
US4666508A (en) * | 1985-06-25 | 1987-05-19 | Ppg Industries, Inc. | Sulfamoyl urea derivatives |
EP0264467A1 (en) * | 1984-12-03 | 1988-04-27 | Ppg Industries, Inc. | Sulfamoyl urea derivates |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5815962A (ja) * | 1981-07-21 | 1983-01-29 | Mitsui Toatsu Chem Inc | 新規スルホニルウレイド誘導体 |
US4555570A (en) * | 1983-09-29 | 1985-11-26 | Ortho Pharmaceutical Corporation | Substituted 4-alkyl-2-(1H) quinazolinone-1-alkanoic acid derivatives |
US4560510A (en) * | 1984-04-06 | 1985-12-24 | A. H. Robins Company, Incorporated | Process and intermediates for the preparation of aryl substituted pyrido[1,4]benzodiazepines |
US4622065A (en) * | 1984-11-01 | 1986-11-11 | Ppg Industries, Inc. | Sulfamoyl urea derivatives |
US4741762A (en) * | 1985-06-25 | 1988-05-03 | Ppg Industries, Inc. | Sulfamoyl urea derivatives |
US4696695A (en) * | 1985-10-25 | 1987-09-29 | Ppg Industries, Inc. | Sulfamoyl urea derivatives |
DE3826609A1 (de) * | 1988-08-05 | 1990-02-08 | Hoechst Ag | Heterocyclisch substituierte sulfonylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide oder pflanzenwachstumsregulatoren |
-
1990
- 1990-06-22 US US07/542,564 patent/US5009699A/en not_active Expired - Lifetime
-
1991
- 1991-01-23 DE DE69113131T patent/DE69113131T2/de not_active Expired - Lifetime
- 1991-01-23 ES ES91100816T patent/ES2077084T3/es not_active Expired - Lifetime
- 1991-01-23 EP EP91100816A patent/EP0463287B1/en not_active Expired - Lifetime
- 1991-01-23 AT AT91100816T patent/ATE128124T1/de not_active IP Right Cessation
- 1991-01-23 DK DK91100816.7T patent/DK0463287T3/da active
- 1991-01-24 HU HU53/91A patent/HU217912B/hu unknown
- 1991-01-25 NZ NZ248154A patent/NZ248154A/en unknown
- 1991-01-25 NZ NZ236903A patent/NZ236903A/en unknown
- 1991-01-25 IE IE26991A patent/IE70909B1/en not_active IP Right Cessation
- 1991-01-25 AU AU70014/91A patent/AU639064B2/en not_active Expired
- 1991-01-25 FI FI910387A patent/FI102749B/fi active
- 1991-01-25 NO NO910299A patent/NO300039B1/no not_active IP Right Cessation
- 1991-01-28 IN IN82/CAL/91A patent/IN171430B/en unknown
- 1991-01-28 ZA ZA91625A patent/ZA91625B/xx unknown
- 1991-01-29 IL IL9708491A patent/IL97084A/en not_active IP Right Cessation
- 1991-01-29 IL IL11166791A patent/IL111667A/en not_active IP Right Cessation
- 1991-02-01 PL PL91294042A patent/PL165824B1/pl unknown
- 1991-02-01 PL PL91288919A patent/PL164558B1/pl unknown
- 1991-02-04 EG EG6991A patent/EG19322A/xx active
- 1991-02-04 JP JP3033456A patent/JP2975698B2/ja not_active Expired - Lifetime
- 1991-02-05 AR AR91318993A patent/AR247558A1/es active
- 1991-02-09 CN CN91101025A patent/CN1033452C/zh not_active Expired - Lifetime
- 1991-02-15 PT PT96775A patent/PT96775B/pt not_active IP Right Cessation
- 1991-02-18 RO RO146949A patent/RO108345B1/ro unknown
- 1991-02-19 BR BR919100669A patent/BR9100669A/pt not_active IP Right Cessation
- 1991-02-22 BG BG93905A patent/BG60302B2/bg unknown
- 1991-02-25 UA UA4894717A patent/UA25934A1/uk unknown
- 1991-02-25 RU SU914894717A patent/RU2002419C1/ru active
- 1991-02-28 KR KR1019910003418A patent/KR0173988B1/ko not_active IP Right Cessation
- 1991-03-07 MY MYPI91000355A patent/MY104634A/en unknown
- 1991-04-09 CA CA002040068A patent/CA2040068C/en not_active Expired - Lifetime
- 1991-05-29 TR TR91/0553A patent/TR25504A/xx unknown
- 1991-06-20 SK SK1896-91A patent/SK280186B6/sk not_active IP Right Cessation
- 1991-06-20 CZ CS911896A patent/CZ282590B6/cs not_active IP Right Cessation
- 1991-06-21 SI SI9111101A patent/SI9111101A/sl unknown
- 1991-06-21 YU YU110191A patent/YU48482B/sh unknown
-
1993
- 1993-02-09 RU RU9393004468A patent/RU2071257C1/ru active
- 1993-05-19 AU AU38696/93A patent/AU647720B2/en not_active Expired
-
1994
- 1994-01-31 LT LTIP1865A patent/LT3814B/lt not_active IP Right Cessation
- 1994-11-17 IL IL11166794A patent/IL111667A0/xx unknown
-
1995
- 1995-02-07 CN CN95100195A patent/CN1069813C/zh not_active Expired - Lifetime
- 1995-09-21 GR GR950401497T patent/GR3017455T3/el unknown
-
1998
- 1998-01-05 HK HK98100066A patent/HK1001056A1/xx not_active IP Right Cessation
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5813962A (ja) * | 1981-07-17 | 1983-01-26 | 株式会社デンソー | 自動車用冷凍サイクル制御装置 |
GB2113217A (en) * | 1982-01-12 | 1983-08-03 | Ciba Geigy Ag | Triaza compounds |
EP0184122A2 (en) * | 1984-12-03 | 1986-06-11 | Ppg Industries, Inc. | Sulfamoyl urea derivatives |
EP0264467A1 (en) * | 1984-12-03 | 1988-04-27 | Ppg Industries, Inc. | Sulfamoyl urea derivates |
US4666508A (en) * | 1985-06-25 | 1987-05-19 | Ppg Industries, Inc. | Sulfamoyl urea derivatives |
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