CN1057756C - 一种除草组合物及其制备方法 - Google Patents
一种除草组合物及其制备方法 Download PDFInfo
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- CN1057756C CN1057756C CN95120571A CN95120571A CN1057756C CN 1057756 C CN1057756 C CN 1057756C CN 95120571 A CN95120571 A CN 95120571A CN 95120571 A CN95120571 A CN 95120571A CN 1057756 C CN1057756 C CN 1057756C
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- C—CHEMISTRY; METALLURGY
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Abstract
本发明涉及已知式(I)化合物N-(4-氟-苯基)-N-异丙基-氯乙酰胺作为选择性除草组合物活性物质的用途，例如用于玉米栽培中的除草，以及这种活性化合物的新制备方法。在20-150℃温度，一种如甲苯的惰性稀释剂存在，不加酸结合剂的条件下N-异丙基-4-氟-苯胺与大约等摩尔的氯乙酰氯，发生反应可以获得收率很高的式(I)化合物。
Description
本发明涉及已知化合物N-(4-氟-苯基)-N-异丙基-氯乙酰胺用作选择性除草组合物活性化合物的用途及该化合物的新的制备方法。
N-(4-氟-苯基)-N-异丙基-氯乙酰胺作为农用化学物质的一个中间体已经公开(参见DE-OS(德国公开说明书)2633159，美国专利4140774，美国专利4418021)。但是，上述化合物作为一种除草剂至今尚未公开。
现在发现以下式(I)化合物N-(4-氟-苯基)-N-异丙基-氯乙酰胺非常适合用于选择性除众多栽培植物的杂草。
本发明公开了一种除草组合物，其特征在于，含有式(I)化合物N-(4-氟-苯基)-N-异丙基-氯乙酰胺，以及与其相混合的增溶剂和表面活性剂。
本发明还公开了除草组合物的制备方法，其特征在于把N-(4-氟-苯基)-N-异丙基-氯乙酰胺与增溶剂和/表面活性剂混合。
迄今为止，在吡啶存在下用N-异丙基-4-氟-苯胺与氯乙酰氯反应制备式(I)化合物的方法已经公开。但是发现，以工业规模实现盐酸吡啶反应生成吡啶非常复杂。
另外，通过N-异丙基-苯胺和氯乙酸和磷酰氯或三氯化磷反应制备其类似物化合物N-(异丙基-苯基)-氯乙酰胺也已经公开(参见美国专利3960948)。但是，这个制备方法的产率不太令人满意，而且还必须通过沉淀磷酸盐处理含磷的废水。
现在发现，在20℃-150℃温度下，在一种如甲苯的惰性稀释剂存在下，不加酸结合剂的条件下，N-异丙基-4-氟-苯胺与大约相等摩尔量的氯乙酰氯发生反应，所获得的式(I)化合物的收率很高。
这种制备方法不产生废水，所释放的氯化氢可以再为他用。
合成式(I)化合物的反应过程可以用下列反应式概括：
制备式(I)化合物所需的原料物质均为已知化合物。
式(I)化合物可以用于脱叶剂，干燥剂，阔叶植物的破坏剂，特别是用作除草剂。这里的杂草最广义地理解为生长在不需要地方的所有植物。
例如，式(I)化合物可以用于以下相关植物：
下列属的双子叶杂草：芥属，独行菜属，猪殃殃属，繁缕属，母菊属，春黄菊属，牛膝菊属藜属，荨麻属，千里光属，苋菜红属，马齿苋属，苍耳属，旋花属，番藷属，蓼属，田菁属，土荆芥属，蓟属，飞廉属，苦苣属，茄属，蔊菜属，
菜属，母草属，野芝麻属，婆婆纳属，麻属，亦模属，茄属，堇菜属，黄鼠狼花属，罂粟属，矢车菊属，车轴草属，毛茛属，蒲公英属。
下列属的双子叶栽培植物：棉属，大豆属，恭菜属，胡萝卜属，菜豆属，碗豆属，茄属，亚麻属，番藷属，巢菜属，烟草属，番茄属，落花生属，芥属，萵苣属，黄瓜属和南瓜属。
下列属的单子叶杂草：稗属，狗尾草属，黍属，马唐属，梯牧草属，早熟禾属，羊茅属，蟋蟀草属，臂形草属，黑麦草属，雀麦属，燕麦属，莎草属，蜀黍属，冰草属，狗牙根属，雨久花属，飘拂草属，慈菇属，荸荠属，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，Apera。
下列属的单子叶载培植物：稻米属，玉米属，小麦属，大麦属，燕麦属，黑麦属，蜀黍属，黍属，甘蔗属，凤梨属，天门冬属，大蒜属。
但是，式(I)化合物的用途不只限于这些属，还能以同样的方式扩展到其它植物。
依浓度而定，式(I)化合物适合于全部去除如长在工地，铁轨，有或没有植树的道路和广场上的杂草。同样，这种化合物可用于去除多年生栽培植物的杂草，例如，种植的树林，栽培的装饰树，果园，葡萄园，柑橘园，胡桃园，香蕉园，咖啡园，茶园，橡胶园，油棕榈园，可可园，栽培的水果和田垄以及草坪、草皮、牧场的杂草。还可用于选择性去除一年生栽培植物的杂草。
本发明的式(I)化合物特别适用于选择性去除单子叶栽培植物的单子叶和双子叶杂草。
可以将式(I)化合物转化为常用制剂，如溶液，乳液，湿粉，悬浮液，粉末，粉尘剂，膏剂可溶性粉末，颗粒，悬乳剂浓缩物，浸透有活性化合物的天然和合成物质以及包有聚合物质的微胶囊。
这些制剂可用已知的方法来制备，例如将活性化合物与增溶剂相混合，这种增容剂是液体溶剂和/或固体载体。还可选择使用表面活性剂，它们是乳化剂和/或分散剂和/或发泡剂。
如果用水作为一种增溶剂，有机溶剂也可用作辅助溶剂等。适合作液体溶剂的主要有：芳族化合物，如二甲苯，甲苯或烷基萘；氯化芳族化合物和氯化脂族烃，如氯苯，氯乙烯或二氯甲烷；脂族烃，如环己烷或链烷烃，例如石油馏分，矿物和植物油；醇类，如丁醇或二元醇以及它们的醚和酯；酮类如丙酮，甲基异丁酮或环己酮；强极性溶剂，如二甲基甲酰胺和二甲基亚砜和水。
适合作固体载体的有：铵盐和磨碎的天然矿物以及磨碎的合成矿物等。天然矿物如陶土，粘土，滑石，白垩，石英，白土，蒙脱土或硅藻土；合成矿物如高高分散性硅石，矾土和硅酸盐。适合作固体载体的颗料有：粉碎的天然岩石，无机、有机粉末的合成颗粒以及有机物的颗粒等。天然岩石如方解石，云石，浮石，海浮石和白云石；有机物颗粒如锯末，椰子壳，玉米蕊和烟草茎。适合作乳化剂和/或发泡剂的有：非离子、阴离子乳化剂，烷芳基聚乙二醇醚，烷基磺酸盐，烷基硫酸盐，芳基磺酸盐以及蛋白水解产物等。非离子、阴离子乳化剂如聚氧乙烯脂肪酸酯，聚氧乙烯脂肪醇脂。适合作分散剂的有：木素亚硫酸盐废液和甲基纤维素等。
在制剂中可以使用粘合剂如羧甲基纤维素、以粉末、颗粒或乳胶形式的天然和合成聚合物如阿拉伯树胶，多元醇，聚乙酸盐以及天然磷脂如脑磷脂和卵磷脂和合成磷脂。另外添加剂还可以是矿物油和植物油。
还可以使用着色剂，有机染料和微量营养素。着色剂如氧化铁，氧化钛和普鲁士蓝的无机颜料等。有机染料，如茜素染料，偶氮染料和金属酞菁染料。微量营养素，如铁、锰、硼、铜、钴、钼和锌盐。
活性化合物在制剂全部组分中所占的重量百分比为0.1～95％，优选0.5～90％。
用于除草时，本发明的式(I)化合物本身或它们的制剂可以与可接受的已知除草剂、成品制剂或罐装混合物相混合使用。
适合于该混合物的除草剂为已知除草剂，有酰苯胺类，如吡氟草胺和敌稗；芳基羧酸类，如敌草定，甲氧二氯苯酸和毒草定；芳基氧链烷酸(aryloxyalkanoic acids)类，如2，4-D，2，4-DB，2，4-DP，氟草烟MCPA，MCPP和乙氯草定；芳氧基-苯氧基-链烷酯类，如2，4-滴苯丙酸甲酯，噁唑禾草灵，吡氟禾草灵，吡氟氯禾灵和喹禾灵；氮杂苯酮类(azinones)，如氯哒酮(chloridazon)和氟哒酮；氨基甲酸酯类，如氯苯胺灵，甜草灵，甲二威灵、和苯胺灵；乙酰氯苯胺类，如杂草锁，乙基乙草胺，丁基锁，吡草胺，甲氧毒草胺，丙草胺和毒草胺；二硝基苯胺类，如磺胺乐灵，Pendimethalin和氟乐灵；二苯醚类，如三氟羧草醚，甲酯除草醚，乙羧氟草醚，氟黄胺草醚，halosafen，乳氟禾草灵和乙氧氟甲草醚；脲类，如绿麦隆，敌草降，优草隆，异丙隆，利谷隆和噻唑隆；羟胺类，如alloxydim，烯草酮，噻草酮，稀禾定和肟草酮；咪唑啉酮类，如咪草烟，咪草酯，灭草烟和灭草喹；腈类，如溴草腈，敌草腈和碘草腈；氧乙酰胺类，如苯噻草胺；磺酰脲类，如amidosulfuron，苄嘧黄隆，氯嘧黄隆，绿黄隆，醚黄隆，甲黄隆，烟嘧黄隆，氟嘧黄隆，吡嘧黄隆，噻黄隆，醚苯黄隆和苯黄隆；硫代氨基甲酸盐类，如异丁草丹，环己丹，二氯烯丹，EPTC，禾草畏，环草丹，苄草丹，thiobencarb和三氯烯丹；三嗪类，如阿特拉津，丙腈津，西玛津，西玛净，特丁草净和特丁津；三嗪酮类(triazinones)，如己苯嗪(hexazinone)，甲苯嗪和赛克嗪；其它，如氨三唑，呋草黄，苯达松，环庚草醚，异恶草酮，clopyralid，草吡唑，氟硫草定，甜菜呋，氟咯草酮，草铵膦，草甘膦，异恶草胺，pyridate，二氯喹啉酸，喹草酸，sulphosate和tridiphane。
还可以与其它已知活性化合物混合，如杀菌剂，杀虫剂、杀螨剂，杀线虫剂，鸟拒斥剂，植物营养剂和土壤改良剂。
式(I)化合物可以以它的制剂形式或经过进一步稀释制备的应用形式使用，例如，预备溶液，悬浮液，乳液，粉末，膏和颗粒。以常规方法如通过浇水，喷洒，喷雾或撒播使用。
植物出现之前和之后均可使用式(I)化合物，在播种之前可以将它掺入土壤中。
使用活性化合物的量可以在一个很大范围内变化，基本上是根据所需效果而定。通常，使用量为每公顷土壤表面积10g-10kg活性化合物，优选量为每公顷50g-5kg。
式(I)化合物的方法和用途可以用下面的实施例说明。制备方法实施例：
将15.3g(0.1摩尔)的4-氟-N-异丙基-苯胺溶于100ml甲苯，在60℃下将11.3g(0.1摩尔)的氯乙酰氯滴入搅拌好的溶液中。混合物在沸点下加热90分钟；然后，稍微冷却混合物，先在水泵真空下蒸馏，最后在油泵真空下蒸馏，仔细去掉溶剂。
得到22.9g(理论的96.5％)N-(4-氟-苯基-N-异丙基-氯乙酰胺，为澄清残余液，折射率1.5210。用途实施例：
出现前试验
溶剂：5份重量的丙酮
乳化剂：1份重量的烷芳基聚乙二醇醚
l份重量的有效化合物与以上数量的溶剂混合，加入以上数量的乳化剂，并且用水将浓缩物稀释到所需浓度。
将试验植物的种子种入一般土壤中。24小时后，用活性化合物的制剂浇土壤。每单位面积浇水的量最好保持不变，制剂中活性化合物的浓度并不重要，只有每单位面积所用活性化合物的量才是决定性因素。3周后，与未处理对照组的生长情况相比较，用损害百分比评价这些植物的损害程度。
图表表示：
0％＝无效(类似未处理对照组)
100％＝全部破坏
试验中把式(I)化合物与具有良好耐药性的农作物如玉米等混合，表示有效除草作用(cf·表A)。
表A：出现前试验/温室
| 应用评价 | 玉米 | cynodon | Echinochloa | 狗尾草 | 苋菜红 | Galinsoga |
| 1000克/公顷(I) | 0 | 100 | 100 | 100 | 90 | 95 |
Claims (2)
1.除草组合物，其特征在于含有式(I)化合物N-(4-氟-苯基)-N-异丙基-氯乙酰胺以及与其相混合的增溶剂和/或表面活性剂。
2.除草组合物的制备方法，其特征在于把N-(4-氟-苯基)-N-异丙基-氯乙酰胺(I)与增溶剂和/或表面活性剂混合。
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|---|---|---|---|---|
| USRE26961E (en) * | 1968-05-27 | 1970-10-06 | Ci. aoln | |
| DE1793110A1 (de) * | 1968-08-02 | 1971-12-16 | Basf Ag | Substituierte Saeureanilide |
| GB1490985A (en) | 1974-02-14 | 1977-11-09 | Lankro Chem Ltd | Processes for the preparation of substituted chloroacylanilides |
| DE2633159C2 (de) | 1976-07-23 | 1982-05-27 | Hoechst Ag, 6000 Frankfurt | Phosphorhaltige Verbindungen, Verfahren zu ihrer Herstellung, sowie diese Verbindungen enthaltende herbizide Mittel |
| NL7700930A (nl) | 1976-02-04 | 1977-08-08 | Hoechst Ag | Plantenbeschermingsmiddel. |
| US4453965A (en) | 1977-07-13 | 1984-06-12 | Patel Natu R | N-Isopropylcarbanilylmethyl dithiophosphates as pre-emergent herbicides |
| US4418021A (en) * | 1977-07-13 | 1983-11-29 | Gulf Oil Corporation | N-Isopropylcarbanilylmethyl dithiophosphates |
| JPS63119447A (ja) * | 1986-11-06 | 1988-05-24 | Hokko Chem Ind Co Ltd | アニリド誘導体および除草剤 |
| JPS63126847A (ja) * | 1986-11-17 | 1988-05-30 | Hokko Chem Ind Co Ltd | Ｎ−置換アニリン誘導体およびその製法 |
-
1994
- 1994-10-25 DE DE4438001A patent/DE4438001A1/de not_active Withdrawn
-
1995
- 1995-10-12 ES ES98115670T patent/ES2158636T3/es not_active Expired - Lifetime
- 1995-10-12 EP EP95116098A patent/EP0709368B1/de not_active Expired - Lifetime
- 1995-10-12 EP EP98115670A patent/EP0884304B1/de not_active Expired - Lifetime
- 1995-10-12 DE DE59509391T patent/DE59509391D1/de not_active Expired - Lifetime
- 1995-10-12 DE DE59505498T patent/DE59505498D1/de not_active Expired - Fee Related
- 1995-10-12 ES ES95116098T patent/ES2129727T3/es not_active Expired - Lifetime
- 1995-10-18 US US08/544,751 patent/US5639713A/en not_active Expired - Fee Related
- 1995-10-20 KR KR1019950036418A patent/KR100399764B1/ko not_active IP Right Cessation
- 1995-10-23 IL IL11571995A patent/IL115719A/xx not_active IP Right Cessation
- 1995-10-24 JP JP29888495A patent/JP3817657B2/ja not_active Expired - Lifetime
- 1995-10-25 CN CN95120571A patent/CN1057756C/zh not_active Expired - Fee Related
-
1997
- 1997-01-30 US US08/792,312 patent/US5831126A/en not_active Expired - Lifetime
-
2000
- 2000-01-10 CN CN00101059A patent/CN1107051C/zh not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1316782A (en) * | 1969-06-07 | 1973-05-16 | Eszakmagyarorszagi Vegyijuvek | Process for the preparation of substituted chloroacylanilides |
| US4021483A (en) * | 1975-07-25 | 1977-05-03 | American Cyanamid Company | 2-Chloro-N-isopropyl-2',3'-dimethylacetanilide as a herbicidal agent |
Also Published As
| Publication number | Publication date |
|---|---|
| KR960013199A (ko) | 1996-05-22 |
| ES2129727T3 (es) | 1999-06-16 |
| EP0709368A1 (de) | 1996-05-01 |
| US5831126A (en) | 1998-11-03 |
| US5639713A (en) | 1997-06-17 |
| DE59505498D1 (de) | 1999-05-06 |
| EP0884304A2 (de) | 1998-12-16 |
| CN1275561A (zh) | 2000-12-06 |
| EP0884304A3 (de) | 1999-02-03 |
| EP0884304B1 (de) | 2001-07-04 |
| JP3817657B2 (ja) | 2006-09-06 |
| CN1107051C (zh) | 2003-04-30 |
| DE59509391D1 (de) | 2001-08-09 |
| IL115719A0 (en) | 1996-01-19 |
| KR100399764B1 (ko) | 2003-12-06 |
| CN1131143A (zh) | 1996-09-18 |
| EP0709368B1 (de) | 1999-03-31 |
| IL115719A (en) | 2000-06-01 |
| ES2158636T3 (es) | 2001-09-01 |
| DE4438001A1 (de) | 1996-05-02 |
| JPH08225407A (ja) | 1996-09-03 |
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