CN1306873C - 基于1－(2－氯苯基)－4－(n－环己基－n－乙基氨基羰基)－1,4－二氢－5h－四唑－5－酮和敌稗的选择性除莠剂 - Google Patents
基于1－(2－氯苯基)－4－(n－环己基－n－乙基氨基羰基)－1,4－二氢－5h－四唑－5－酮和敌稗的选择性除莠剂 Download PDFInfo
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- CN1306873C CN1306873C CNB981040810A CN98104081A CN1306873C CN 1306873 C CN1306873 C CN 1306873C CN B981040810 A CNB981040810 A CN B981040810A CN 98104081 A CN98104081 A CN 98104081A CN 1306873 C CN1306873 C CN 1306873C
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
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- A—HUMAN NECESSITIES
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- 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
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
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- A01N29/10—Halogen attached to an aliphatic side chain of an aromatic ring system
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- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
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- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
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Abstract
包含(a)1-(2-氯苯基)-4-(N-环己基-N-乙基氨基羰基)-1，4-二氢-5H-四唑-5-酮和(b)N-(3，4-二氯苯基)丙酰胺(Propanil)的新的除莠活性化合物组合在适当的重量比下表现出增效活性，可以用作多种作物(例如稻米和小麦)的选择性除莠剂。
Description
本发明涉及已知化合物1-(2-氯苯基)-4-(N-环己基-N-乙基氨基羰基)-1，4-二氢-5H-四唑-5-酮和已知的活性化合物敌稗(Propanil)的新的除莠增效活性化合物组合，它可以成功地用来选择性控制多种作物的杂草。
化合物1-(2-氯苯基)-4-(N-环己基-N-乙基氨基羰基)-1，4-二氢-5H-四唑-5-酮也称为1-(2-氯苯基)-4-(N-环己基-N-乙基氨基甲酰基)-5(4H)-四唑啉酮或1-(2-氯苯基)-N-环己基-N-乙基-4，5-二氢-5-氧代-1H-四唑-1-甲酰胺，是公知的除莠活性物质(参见EP 612 735/US 5362704)。然而，该化合物单独的除莠活性并不总能令人满意。
通常称为敌稗的化合物(也可以称为N-(3，4-二氯苯基)丙酰胺或3′，4′-二氯-3-戊酮-N-丙酰苯胺)是长期以来已知的除莠活性化合物，并且被作为市售产品的成分。然而，该化合物单独的除莠活性也并不总能令人满意。
令人惊讶的是，生物学试验现在表明一种新的活性化合物组合在除莠活性方面具有明显的增效作用，可以用作有效的宽范围组合产品，特别适用于作物例如稻米和小麦(尤其是稻米)的杂草的选择性控制。所述组合包括
(a)有效量的式(I)的1-(2-氯苯基)-4-(N-环己基-N-乙基氨基羰基)-1，4-二氢-5H-四唑-5-酮：
和
(b)有效量的式(II)的N-(3，4-二氯苯基)丙酰胺(Propanil)：
令人惊讶的是，本发明的活性化合物组合的除莠活性比各独立的活性化合物的活性之和高得多。
这意味着，出现了意外的增效作用，而不仅仅是作用的补充。许多作物都可以耐受该新的活性化合物组合，甚至难以控制的杂草都可以用本发明的新活性化合物组合加以控制。
本发明的活性组合物组合可以用于例如下述植物：
双子叶杂草种类：芥属、独行菜属、拉拉藤属、繁缕属、母菊属、青黄菊属、牛膝菊属、藜属、荨麻属、千里光属、苋属、马齿苋属、苍耳属、旋花属、番薯属、蓼属、田菁属、豚草属、蓟属、飞廉属、枯苣菜属、茄属、萍菜属、节节菜属、母草属、野芝麻属、斑鸠菊属、苘麻属、刺酸模属、曼陀螺属、堇菜属、鼬瓣花属、罂粟属、矢车菊属、车轴草属、毛茛草属和蒲公英属。
双子叶作物种类：棉属、大豆属、甜菜属、胡萝卜属、菜豆属、豌豆属、茄属、亚麻属、番薯属、野豌豆属、烟草属、番茄属、落花生属、芸苔属、莴苣属、香瓜属和姜黄属。
单子叶杂草种类：稗属、狗尾草属、黍属、马唐属、梯牧草属、早熟禾属、狐茅属、
属、臂形草属、毒麦属、雀麦属、燕麦属、莎草属、高粮属、冰草属、狗牙根属、雨久花属、飘拂草属、慈姑属、荸荠属、蔗草属、雀稗属。鸭嘴草属、尖瓣花属、龙爪茅属、剪股颖属、看麦娘属和Apera。
单子叶作物种类：稻属、玉蜀黍属、小麦属、大麦属、燕麦属、黑麦属、高粮属、黍属、甘蔗属、凤梨属、天门冬属和葱属。
然而，本发明的活性化合物组合并不局限于这些属类，也同样延伸到其它植物。
本发明的活性化合物组合的增效作用在特定的浓度比时特别显著。然而，活性化合物组合中活性化合物的重量比可以在较宽的范围内改变。每重量份式(I)活性化合物一般使用0.10-1000重量份、优选0.05-500重量份、特别优选0.1-100重量份式(II)活性化合物。
该活性化合物或活性化合物组合可以转变为常规制剂，例如溶液剂、乳剂、可湿性粉剂、悬浮液、粉末剂、粉剂、糊剂、可溶性粉剂、粒剂、悬乳液浓缩物、用活性化合物浸渍的天然或合成材料和在聚合物材料中的微胶囊。
这些制剂可以通过常规方式生产，例如将活性化合物与增量剂(即液体溶剂和/或固体载体)可选地与表面活性剂(即润滑剂和/或分散剂和/或泡沫形成剂)一起混合。
如果用水作增量剂，则可以用例如有机溶剂作辅助溶剂。适宜的液体溶剂主要有：芳族化合物例如二甲苯、甲苯或烷基萘、氯代芳族化合物和氯代脂族烃例如氯苯、氯乙烯或二氯甲烷，脂族烃例如环己烷或石蜡。例如石油馏分、矿物油和植物油，醇类化合物例如丁醇和乙二醇及其醚和酯，酮类化合物例如丙酮、甲乙酮、甲基异丁基酮或环己酮，强极性溶剂例如二甲基甲酰胺和二甲基亚砜，和水。
适宜的固体载体是例如：铵盐和土地天然矿物质例如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土，和土地合成矿物质例如细碎分散的二氧化硅、氧化铝和硅酸盐；适宜的粒剂用固体载体是例如压碎和粉碎的天然岩石例如方解石、大理石、浮石，海泡石和白云石，或者无机合成粒剂和有机食物，和有机材料的粒剂例如锯末、椰子壳、玉米芯和烟草杆；适宜的润滑剂和/或泡沫成形剂是例如非离子和阴离子型乳化剂，例如聚氧化乙烯脂肪酸酯、聚氧化乙烯脂肪醇醚例如烷基芳基聚乙二醇醚、烷基磺酸盐、烷基硫酸盐、芳基硫酸盐和蛋白质水解产物；适宜的分散剂是例如木素-亚硫酸盐废液和甲基纤维素。
在制剂中可以使用增粘剂例如羧甲基纤维素和粉末、颗粒或胶乳形式的天然和合成聚合物例如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯，或者天然磷脂例如脑磷脂和卵磷脂，和合成磷脂。其它的添加剂可以是矿物油和植物油。
还可以使用例如着色剂例如无机颜料例如氧化铁；氧化钛和普鲁士蓝，和有机染料例如茜素染料，偶氮染料和金属酞菁染料和微量营养剂例如铁、镁、硼、铜、钴、钼和锌的盐。
制剂通常包括0.1-95％(重量)活性物质和可选的安全剂例如化合物N-(4-甲基苯基)-N′-(1-甲基-1-苯基乙基)脲(SK-223，dymvon)，优选0.5-90％(重量)的活性化合物和可选的安全剂。
一般来说，本发明的活性化合物组合是已经混合的形式。然而，活性化合物组合中的活性化合物也可以独立地制备，使用时混合，也就是说以罐装合剂的形式施用。
该新的活性化合物组合直接或以其制剂的形式以与其它已知除莠剂的混合物的形式使用，还可以是最终制剂或罐装合剂。也可以是与其它其它已知活性化合物例如杀真菌剂、杀昆虫剂、杀螨剂、杀线虫剂、鸟驱避剂、生长促进剂、植物营养剂和土壤调节剂的混合物。此外，对于特定的目的特别是使用萌芽后法，混入植物能够耐受的矿物油或植物油(例如″Oleo Dupont 11E″，市面有售)或铵盐例如硫酸铵或硫氰酸铵，作用制剂的另外的添加剂。
新的活性化合物组合可以直接使用，以其制剂的形式或者通过进一步稀释制备的使用形式，例如待用溶液、悬浮液、乳液、粉末、糊剂和粒剂。它们以常规的方式使用例如灌溉、喷洒、喷雾、撒播或撒布。
本发明的活性化合物组合的施用比率可以在一定的范围内变化，它们尤其取决于气候和土壤条件。一般来说，施用比率为每公顷0.05-5kg、优选每公顷0.05-2kg、特别是在每公顷0.1-1.0kg之间。
本发明的活性化合物组合可以在植物萌芽之前或之后施用，即采用萌芽前和萌芽后法。
新活性化合物组合的良好的除莠活性在下面的实施例中显而易见。尽管活性化合物单独时表现出较弱的除莠活性，但其组合都表现出对杂草的非常有效的控制，并且该控制超过了其活性的简单加合。
在除莠剂中，当活性化合物组合的活性超过单独施用活性化合物的时，便出现了增效作用。
对于给定的两种除莠剂的组合预期活性可如下计算(参见COLBY，S.R.；″Calculating synergistic and antagonistic responses of herbicidecombinations″，Weeds 15，第20-22页，1967)：
如果X＝在施用比率为p kg/ha时，除莠剂A(式(I)的活性化合物)的损害百分数
Y＝在施用比率为p kg/ha时，除莠剂B(式(II)的活性化合物)的损害百分数
E＝在施用比率为p kg/ha时，预期除莠剂A和除莠剂B会引起的损害百分数
则E＝X+Y-(X*Y/100)
如果实际损害超过了该计算值，则该组合在活性方面是超加合性的，即表现出增效作用。
下述实施例揭示了本发明的活性化合物组合的除莠活性超过了该计算值，即新的活性化合物组合具有增效作用。
使用实施例：
为制备本试验所需的活性化合物制剂，称出适量的上述式(I)的活性成分的50％浓度水可分散性粉剂(50WP)和活性成分含量为360克/升(360 EC)的上式(II)活性化合物(Propanil)市售乳液浓缩物，用水稀释至所需浓度，通过混合制备两种活性成分的各种组合。
所用缩写的意义如下：
a.i.＝活性成分；
实测值＝测得的损害或活性(％)；
计算值＝用上述COLBY公式计算得到的损害或活性(％)。
试验按照下述的方法在不同的地理位置进行，从不同国家(菲律宾、意大利、日本)观察到的结果由于在各地区非常不同的施用条件有所分散。
实施例A：移植稻米试验(菲律宾)
为制备喷雾制剂，将上述活性成分制剂与水混合。调节浓度，使得施用比率对应于450升水/公顷。
将稻米种子(1-2叶期)移植到水稻田试验场(2.5米×2.5米)中。移植7天后，将喷雾制剂施用到试验区(用手动喷雾器)。处理1天后，给土壤灌溉至5厘米水深；静置水深保持不变。
施用活性化合物4周后，相对于未处理对照组目测评定(％)对稻米植物的损害程度和对萌芽杂草Echinochloa crus galli和Monochoriavaginalis的除莠效果。
数字表示：
0％＝无作用/损害(如同未处理的对照物)
100％＝完全破坏
结果示于下表A中。
表A：移植的稻米(菲律宾)
| 试验植物(损害或作用的百分数) | ||||
| 活性成分或组合 | 施用比率(g a.i./ha) | Echinochloacrus galli实测值计算值 | Monochoriavaginalis实测值计算值 | 稻米(Oryza sp.)实测值 |
| (I)(已知) | 125 | 99 | 97 | 0 |
| (II)(已知) | 900 | 93 | 55 | 0 |
| (I)+(II)(按照本发明) | 125+900 | 100(99.9) | 100(98.7) | 0 |
实施例B：播种稻米试验(菲律宾)
为制备喷雾制剂，将上述活性成分制剂与水混合。调节浓度，使得施用比率对应于450升水/公顷。
将稻米种子播种到水稻田(用水饱和的土壤)试验场(2.5米×2.5米)中。播种7天后，将喷雾制剂施用到试验区(用手动喷雾器)。处理1天后，给土壤灌溉至5厘米水深；静置水深保持不变。
施用活性化合物4周后，相对于未处理对照组目测评定(％)对稻米植物的损害程度和对萌芽杂草Echinochloa crus galli、Monochoriavaginalis和Sphenonclea的除莠效果。
数字表示：
0％＝无作用/损害(如同未处理的对照物)
100％＝完全破坏
结果示于下表B1和B2中。
表B1：播种稻米试验(菲律宾)
| 试验植物(损害或作用的百分数) | |||
| 活性成分或组合 | 施用比率(g a.i./ha) | Monochoriavaginalis实测值 计算值 | 稻米(Oryza sp.)实测值 |
| (I)(已知) | 50 | 68 | 1 |
| (II)(已知) | 900 | 87 | 2 |
| (I)+(II)(按照本发明) | 50+900 | 98(95.8) | 13 |
表B2：播种稻米试验(菲律宾)
| 试验植物(损害或作用的百分数) | ||||
| 活性成分或组合 | 施用比率(g a.i./ha) | Ecbinochloacrus galli实测值 计算值 | Monochoriavaginalis实测值 计算值 | 稻米(Oryza sp.)实测值 计算值 |
| (I)(已知) | 50 | 96 | 62 | 2 |
| (II)(已知) | 900 | 87 | 58 | 3 |
| (I)+(II)(按照本发明) | 50+900 | 100(99.5) | 94(84) | 35 |
实施例C：播种稻米试验(意大利)
为制备喷雾制剂，将上述活性成分制剂与水混合。调节浓度，使得施用比率对应于450升水/公顷。
将稻米种子播种到水稻田(润湿的土壤)试验场(2米×5米)中。播种两周后，将喷雾制剂施用到试验区(用手动喷雾器)。处理3天后，给土壤灌溉至5厘米水深；静置水深保持不变。
施用活性化合物4周后，相对于未处理对照组目测评定(％)对稻米植物的损害程度和对萌芽杂草Echinochloa crus galli、Digitariaascendens，Panicumdichotomiflorm和Polygonum persicaria的除莠效果。
数字表示：
0％＝无作用/损害(如同未处理的对照物)
100％＝完全破坏
结果示于下表C1和C2中。
表C1：播种稻米试验(意大利)
| 试验植物(损害或作用的百分数) | |||
| 活性成分或组合 | 施用比率(g a.i./ha) | Monochoriavaginalis实测值 计算值 | 稻米(Oryza sp.)实测值 |
| (I)(已知) | 300 | 35 | 0 |
| (II)(已知) | 1500 | 45 | 0 |
| (I)+(II)(按照本发明) | 300+1500 | 92(64.3) | 0 |
表C2：播种稻米试验(菲律宾)
| 试验植物(损害或作用的百分数) | |||||
| 活性成分或组合 | 施用比率(g a.i./ha) | Digitariaascendens实测值 计算值 | Panicumdichotomiflorum实测值 计算值 | Polygonumpersicaria实测值 计算值 | 稻米(Oryza sp.)实测值 |
| (I)(已知) | 300 | 70 | 60 | 70 | 0 |
| (II)(已知) | 1500 | 75 | 67 | 70 | 0 |
| (I)+(II)(按照本发明) | 300+1500 | 100(92.5) | 92(87) | 100(91) | 0 |
实施例D：播种稻米试验(温室，日本)
为制备适宜的喷雾制剂，通过与水混合，将上述活性成分稀释至所需的浓度。
给培育植物的容器(尺寸：20cm×20cm×9cm；表面积1/2000Ar)中装上来自水稻田的土壤，将稻米种子和Echinochloa crus galli种子播种到保持在润湿条件下的土壤中。在稻米和Echinochloa crus galli的1.5-2叶期，喷洒稀释的活性成分制剂(叶处理)。制剂的活性成分的浓度并不重要；关键是每单位面积活性成分的施用比率。
处理1天后，给土壤灌溉至5厘米深；随后的试验保持在3厘米水深下进行。
施用活性化合物3周后，相对于未处理对照组目测评定(％)对稻米植物的损害程度(或除莠效果)。
数字表示：
0％＝无作用/损害(如同未处理的对照物)
100％＝完全破坏
结果示于下表D1至D4中。
表D1：温室试验(日本1996)
| 试验植物(损害或作用的百分数) | |||
| 活性成分或组合 | 施用比率(ga.i./ha) | Echinochloacrus galli实测值 计算值 | 稻米、(Oryza sp.)实测值 计算值 |
| (I)(已知) | 50 | 50 | 5 |
| (II)(已知) | 450 | 10 | 0 |
| (I)+(II)(按照本发明) | 50+450 | 80(55) | 5(5) |
表D2：温室试验(日本1996)
| 试验植物(损害或作用的百分数) | |||
| 活性成分或组合 | 施用比率(g a.i./ha) | Echinochloacrus galli实测值 计算值 | 稻米(Oryza sp.)实测值 计算值 |
| (I)(已知) | 100 | 80 | 10 |
| (II)(已知) | 450 | 10 | 0 |
| (I)+(II)(按照本发明) | 100+450 | 93(82) | 10(10) |
表D3：温室试验(日本1996)
| 试验植物(损害或作用的百分数) | |||
| 活性成分或组合 | 施用比率(g a.i./ha) | Echinochloacrus galli实测值 计算值 | 稻米(Oryza sp.)实测值 计算值 |
| (I)(已知) | 50 | 50 | 5 |
| (II)(已知) | 900 | 50 | 0 |
| (I)+(II)(按照本发明) | 50+900 | 90(75) | 5(5) |
表D4：温室试验(日本1996)
| 试验植物(损害或作用的百分数) | |||
| 活性成分或组合 | 施用比率(g a.i./ha) | Echinochloacrus galli实测值 计算值 | 稻米(Oryza sp.)实测值 计算值 |
| (I)(已知) | 100 | 80 | 10 |
| (II)(已知) | 900 | 50 | 0 |
| (I)+(II)(按照本发明) | 100+900 | 100(55) | 10(10) |
Claims (6)
1.选择性除莠组合物，其特征在于含有包括下述两种增效活性化合物的组合：
(a)式(I)的1-(2-氯苯基)-4-(N-环己基-N-乙基氨基羰基)-1，4-二氢-5H-四唑-5-酮：
和
(b)式(II)的N-(3，4-二氯苯基)丙酰胺：
其中，每重量份式(I)活性化合物使用0.1-100重量份式(II)活性化合物。
2.按照权利要求1的选择性除莠组合物，其特征在于每重量份式(I)活性化合物使用4.5-18重量份式(II)活性化合物。
3.按照权利要求1的选择性除莠组合物，其特征在于它除了包含新的活性化合物组合外还包括安全剂。
4.选择性控制杂草的方法，其特征在于使按照权利要求1-3的活性化合物组合作用于杂草和/或其生境。
5.权利要求1-3中任一权项的活性化合物组合在选择性控制杂草中的用途。
6.制备选择性除莠组合物的方法，其特征在于将权利要求1-3的活性化合物组合与增量剂和/或表面活性剂混合。
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| DE19701845 | 1997-01-21 | ||
| DE19701845.9 | 1997-01-21 |
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| CN1296381A (zh) * | 1998-04-15 | 2001-05-23 | 纳幕尔杜邦公司 | 除草混合物 |
| DE10142336A1 (de) * | 2001-08-30 | 2003-03-20 | Bayer Cropscience Ag | Selektive Herbizide enthaltend ein Tetrazolinon-Derivat |
| CN102875540A (zh) * | 2012-10-30 | 2013-01-16 | 南开大学 | 2-苯并恶嗪酮基-5-环己氨基羰基四唑酮的除草活性 |
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| US5362704A (en) * | 1993-02-25 | 1994-11-08 | Nihon Bayer Agrochem K.K. | Herbicidal tetrazolinones |
| CN1129517A (zh) * | 1994-10-18 | 1996-08-28 | 拜尔公司 | 基于芳基尿嘧啶类的用于水稻栽培中的除莠剂 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5362704A (en) * | 1993-02-25 | 1994-11-08 | Nihon Bayer Agrochem K.K. | Herbicidal tetrazolinones |
| CN1129517A (zh) * | 1994-10-18 | 1996-08-28 | 拜尔公司 | 基于芳基尿嘧啶类的用于水稻栽培中的除莠剂 |
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| ES2136035A1 (es) | 1999-11-01 |
| CN1195475A (zh) | 1998-10-14 |
| KR100479612B1 (ko) | 2005-06-17 |
| JP4068707B2 (ja) | 2008-03-26 |
| IT1298151B1 (it) | 1999-12-20 |
| KR19980070559A (ko) | 1998-10-26 |
| CO5040024A1 (es) | 2001-05-29 |
| BR9800354A (pt) | 1999-09-08 |
| TW490288B (en) | 2002-06-11 |
| DE19801637A1 (de) | 1998-07-23 |
| ID19573A (id) | 1998-07-23 |
| ITMI980081A1 (it) | 1999-07-19 |
| ES2136035B1 (es) | 2000-05-01 |
| US5928991A (en) | 1999-07-27 |
| PA8444801A1 (es) | 2001-10-10 |
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