CN1346596A - 一种除草的杂环基氧乙酰替取代苯胺类化合物及其制备方法以及它们的除草剂组合物 - Google Patents
一种除草的杂环基氧乙酰替取代苯胺类化合物及其制备方法以及它们的除草剂组合物 Download PDFInfo
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- CN1346596A CN1346596A CN 01134146 CN01134146A CN1346596A CN 1346596 A CN1346596 A CN 1346596A CN 01134146 CN01134146 CN 01134146 CN 01134146 A CN01134146 A CN 01134146A CN 1346596 A CN1346596 A CN 1346596A
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Abstract
本发明涉及作为农作物除草剂的新的杂环基氧乙酰替取代苯胺类化合物的制备方法及它所作为除草剂的应用。本发明涉及通式(I)的新的杂环基氧乙酰替苯胺类化合物(其中Het、R1、R2、n的定义如说明书中所述)及其制备方法,本发明活性化合物对禾本科杂草和部分主要阔叶杂草高效,对棉花、玉米、水稻、大豆、田间作物安全。
Description
技术领域
本发明涉及作为农作物除草剂的新的杂环基氧乙酰替取代苯胺类化合物的制备方法及它所作为除草剂的应用。
背景技术
氧乙酰替苯胺类化合物最早由德国拜耳公司合成并发现具有除草活性，国外已有不少专利报道。例如：US4509971，US4833243，US4968342，EP626380，EP709380，DE4230903，DE19509044。专利中所涉及的部分化合物具有除草活性，并由德国拜耳公司-日本特殊农药公司成功开发出稻田除草剂苯噻草胺(mefenacet 2-苯并噻唑-2-基氧-N-甲基乙酰替苯胺)。
但是已知的氧乙酰替苯胺类化合物的除草活性及其适用作物并不完全令人满意，这些已知化合物用量大，只对禾本科杂草有效，对阔叶杂草防效差，而且适用作物面窄，只适合于水稻。
发明内容
本发明的目的就是为了解决上述问题，提出一种具有高效的除草活性的除草的杂环基氧乙酰替取代苯胺类化合物及其制备方法以及它们的除草剂组合物。
本发明的技术解决方案：
本发明提供一种新的通式(I)的杂环基氧乙酰替苯胺类化合物
其中，
n代表1、2、或3。
R1代表一直链或支链的烷基、链烯基、链炔基；或一被卤原子、氰基取代的直链或支链的烷基、链烯基、链炔基。
R2代表烷基、烷氧基、硝基、氰基；或氟、氯、溴、碘元素；或卤代烷基。
Het代表一可任意地被氟、氯、溴、碘、甲基、乙基、异丙基、三氟甲基、二氟甲基、一氯二氟甲基、二氯二氟甲基、甲硫基、乙硫基、苯基或卤代苯基取代的1，2，4-噻二唑基；1，3，4-噻二唑基或可任意地被氟、氯、溴、碘、三氟甲基、二氟甲基、甲基、甲氧基取代的苯并噻唑基、或喹喔啉基或嘧啶基。
一种通式(I)的化合物的制备方法，其特征在于，在一定条件下，经由通式(II)的杂环化合物与通式(III)的N-烷基-N-取代苯基羟基乙酰胺类化合物反应，
Het-X (II)其中，Het代表的意义如前所述；X代表卤素原子或烷基磺酰基；其中n、R1、R2代表的意义如前所述。
一种除草剂组合物，其特征在于含有至少一种通式(I)的化合物作为有效成分。
本发明提供通式(I)的活性化合物具有高效的除草活性，对禾本科杂草及主要阔叶杂草高效，对棉花、大豆、玉米及水稻安全。与现有常规除草剂乙草胺、丁草胺、苯噻草胺相比，本发明化合物活性更高、杀草谱更广、安全性更高，适用作物更宽。
具体实施方式
本发明提供通式(I)的化合物可由通式(II)的杂环化合物与通式(III)的N-烷基-N-取代苯基羟基乙酰胺在一定条件下经下列反应制得。
其中，Het、n、R1、R2、X代表的意义同上。作为起始物使用的通式(II)的杂环化合物是已知的，或可由已知的方法制备，参见(DE3234531，DE4003436，US5856499，JP63-283870)
作为另一起始物使用的通式(III)的N-烷基-N-取代苯基羟基乙酰胺也是已知的，或可由已知的方法制备，参见(US4334073，US4509971，US5895818，JP59-190953)。
本发明中制备的通式(III)的化合物部分是新的，在以前文献中没有出现。
本发明提供制备通式(I)的化合物的方法宜在合适溶剂中进行：芳烃类，例如甲苯，二甲苯，C9芳烃；卤代烷烃类，例如二氯甲烷、氯仿、四氯化碳；醚类，例如***、二丙醚、二丁醚、乙二醇、二甲醚、四氢呋喃；醇类，例如甲醇、乙醇、异丙醇、正丁醇；酮类，例如丙酮、丁酮；强极性溶剂，例如乙腈、DMF、DMSO。
本发明提供制备通式(I)的化合物的方法应在缚酸剂存在下进行，优先选用的缚酸剂是碱金属或碱土金属氧化物，例如氧化钠，氧化钾，氧化钙；氢氧化物，例如氢氧化钠、氢氧化钾、氢氧化钙；碳酸盐，例如碳酸钠、碳酸钾、碳酸钙；醇化物，例如甲醇钠、乙醇钠、叔丁醇钠及叔丁醇钾。
根据本发明的又一特征，在进行本发明的方法时，通式(II)的杂环化合物与通式(III)的N-烷基-N-取代苯基羟基乙酰胺的摩尔比可以是0.5-3.0，最好是0.8-1.5。
根据本发明的又一特征，在进行本发明的方法时，反应温度一般在-40℃-+120℃间进行，最好是-20℃-+100℃。
本发明通式(I)的化合物具有除草活性，可用于杀灭如下杂草：
以下各属的双子叶杂草：繁缕属、母菊属、春黄菊属、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、飞廉属、苦苣菜属、茄属、节节菜属、母草属、野芝麻属、婆婆纳属、苘麻属、车轴草属、毛茛属和蒲公英属。
以下各属的单叶杂草：稗属、狗尾草属、黍属、马唐属、早熟禾属、羊茅属、黑麦草属、雀麦属、燕麦属、莎草属、高粱属、冰草属、狗牙根属、雨久花属、慈姑属、荸荠属、雀稗属、鸭嘴草属、看麦娘属和风草属。
本发明通式(I)的活性化合物特别适合于选择地防除棉花、玉米、水稻、大豆作物中的禾本科杂草及部分主要阔叶杂草，尤其适合芽前土壤处理。
本发明的活性化合物可以加工成制剂形式使用，如乳油、悬浮剂、可溶性粉剂、颗粒剂、水乳剂、胶襄剂及其它农业上可接受的制剂形式。
这些制剂可用已知的方法制备，通常将本发明的活性化合物与一定量的载体及表面活性剂(含分散剂)混合而成，其中本发明的活性化合物重量含量是0.01-90％。
适用本发明的载体有液体溶剂和固体。适用的液体溶剂主要有：取代芳烃，如甲苯、二甲苯、C9芳烃；氯代芳族化合物和氯代脂肪烃类；矿物和植物油；醇类，例如丁醇、1，2-乙二醇；强极性溶剂，如DMF、DMSO以及水。
适用的固体载体有，天然矿物，如高岭土、粘土、石英、硅藻土；粉碎合成矿物，如高度分散性的二氧化硅，氧化铝、硅酸盐或轻质碳酸钙。
适用的乳化剂有：非离子和阴离子乳化剂，如烷基芳基聚乙二醇醚、烷基磺酸盐、芳基磺酸盐、烷基硫酸盐；适用的分散剂有木素亚硫酸盐和甲基纤维素。
本发明的活性化合物可以单独使用，也可以与已知的除草剂混合使用以更好地防除杂草。
适用上述混合的已知除草剂有：磺酰脲类，如bensulfuron-methyl，amidosulfuron，triasulfuron，nicosulfuron，primisulfuron-methyl，flupyrsulfuron，trifloxy-sulfuron，ethoxysulfuron，rimsulfuron，cinosulfuron；三嗪类，如metribuzin，cyanazine，simetryne；酰胺类，如butachlor，alachlor，acetochlor，普乐宝，napropamide，propanil，diflufenican，metazachlor；***并嘧啶类，如flumetsulam，metosulam，florasulam，diclosulam；环己二酮类，如sulcotrione，mestrione，isoxaflutole，sethoxydim，tralkoxydim，tepraloxydim，clethodim；二苯醚类，如fomesafen，lactofen，fluoroglycofen-ethyl，ethoxyfen-ethyl；四氢邻苯二甲酰亚胺类，如fluthiacet-ethyl，flumioxazin，flumiclorac-pentyl；***啉酮类，如carfentrazone-ethyl，sulfentrazone，azafenidin；咪唑啉酮类，如imazethapyr，imazamethabenz，imazapyr，imazaguin。
本发明的活性化合物及其组合物可以在芽前或芽后使用，也可以土壤处理使用。下述实施例说明本发明涉及的通式为(I)的化合物的制备和使用。
实施例1：
将8克(32.5毫摩尔)N-(3-氯-4-氟苯基)-N-异丙基羟乙酰苯胺，9.2克(39毫摩尔)2-甲砜基-5-三氟甲基-1，3，4-噻二唑，50毫升甲苯分别加入100毫升反应瓶中，冷却混合物至-5℃-0℃，在一小时内滴入8克25％氢氧化钠溶液，0℃搅拌反应2小时，室温搅拌12小时，经色谱定性分析仍有30％N-(3-氯-4-氟苯基)-N-异丙基羟乙酰苯胺，补加3.6克2-甲砜基-5-三氟甲基-1，3，4-噻二唑，在室温下继续搅拌4小时，然后加入10毫升水，分去水层，水层用2×10毫升甲苯萃取，合并甲苯层，用稀盐酸调节甲苯层至PH中性，并用无水硫酸钠干燥，减压脱尽甲苯，得无色稠状物12.0克，经乙醇结晶得到10.5克(理论值的84％)白色的N-(3-氯-4-氟苯基)-N-异丙基-1，3，4-噻二唑乙酰胺晶体，熔点：88-90℃。
参照实施例1制备方法的一般说明，制得其它的通式(I)的化合物，见表1中。
表1
通式(I)化合物的实施例 
下列实施例涉及通式(III)起始物的制备。
实施例2：步骤1：
将29.5克(0.2摩尔)3-氯-4-氟苯胺，18毫升丙酮依次投入装有120毫升乙酸的250毫升四口反应瓶中，冷却反应温度在20℃以下，在一小时内分批加入10克(0.26摩尔)硼氢化钠，20℃继续反应2小时，然后将反应液倒入500克碎冰中，用80克50％氢氧化钠中和至PH＝12-14，油层析出，分去油层，再用60毫升×2次环已烷萃取水层，合并油层，脱尽环已烷，减压蒸馏得33克(理论值的88％)白色透明的N-异丙基-N-(3-氯-4-氟)乙酰胺，沸点：112-114℃/20mmHg。
步骤2：
在250毫升四口反应瓶中，分别投入21.0克氯乙酸，18克三氯氧磷及100毫升甲苯，加热至60-70℃，在一小时内滴入33克上述实施例制得的胺，升温至110℃回流反应4-6小时，冷却至60℃，加入100毫升水分解未反应的三氯氧磷，分去水层，有机相用饱和碳酸氢钠洗涤至中性，经无水硫酸钠干燥后，不经处理作为下一步反应的原料。
将上述甲苯层，18克无水乙酸钠，3克TEBA，投入250毫升反应瓶中，升温回流8小时，冷却至室温，加水80毫升，分去水层，水层用20毫升×2甲苯萃取，合并有机相，减压脱尽溶剂，得27.0克白色晶体。将所得固体与150毫升甲醇回流反应6小时(加入0.2克片碱)，脱尽溶剂得26克粘稠状液体，冷却后固体析出，经丙酮重结晶得15克N-(3-氯-4-氟苯基)-N-异丙基羟基乙酰胺白色晶体。熔点：69-71℃。
制剂实施例：
下面的实施例说明本发明的除草组合物。
实施例3：
一种可湿性粉剂由下列组成：
活性化合物(化合物I-11) 50％W/W
十二烷基苯磺酸钠 5％W/W
木质素硫酸钠 5％W/W
轻质碳酸钙 40％W/W
实施例4：
一种水溶性粉末由下列组成：
活性化合物(化合物I-11) 50％W/W
十二烷基苯磺酸钠 2％W/W
超细二氧化硅 2％W/W
碳酸氢钠 46％W/W
实施例5：
一种水渗性浓缩物由下列组成：
活性化合物(化合物I-11) 20％W/V
氢氧化钾溶液33％W/V 10％V/V
四氢糖基醇 10％V/V
水 加到100体积
应用实施例：
在下面提供的应用实施例中，使用下面所给出的化合物(苯噻草胺)作为对照物。
实施例6：
盆栽植株活性试验
(1)试样：
I-1、I-2、I-3、I-4、I-5、I-8、I-10、I-11、I-13、I-15、I-16、I-17、，茎叶处理时各称13.3mg，各加溶剂丙酮0.5ml溶解，然后加0.2％的吐温80水乳剂定容至10ml，采用有转盆的喷雾机喷洒，折合着药量为1000g/ha；，土壤处理时各称2.66mg，各加溶剂丙酮0.5ml溶解，然后加0.2％的吐温80水乳剂定容至10ml，采用有转盆的喷雾机喷洒，折合着药量为200g/ha。
(2)试材：
双子叶选用苘麻、反枝苋、藜，单子叶选用稗草、马唐、狗尾草共6种。
(3)试材植株的培育：
芽期土壤处理：6种试材挑选露白种子各10粒，均匀播于直径为12cm塑料盆内，盆内底土为过5目筛土350g，上盖8目筛土50g，盖土吸水后备用。
芽后茎叶处理：6种试材挑选露白种子各10粒，均匀播于直径为12cm塑料盆内，盆内底土为过5目筛土350g，上盖8目筛土50g，盖土吸水后置于温室试验台上培养，12天后试材生长至2-3叶备用。
(4)测试：
将芽期、芽后处理试材分别置于转盘式喷雾机转盘上进行本发明系列化合物的处理，每处理设3个重复，处理后的试材在操作间晾干后移置于温室试验台上培养，30天后检查试材存活株数、地上部分鲜重指标，以空白组作为对照，按以下公式计算药剂处理后的植株的鲜重抑制率和死亡率。
鲜重抑制率＝(对照地上部分鲜重-处理地上部分鲜重)/对照地上部分鲜重×100％
植株死亡率＝(试材总株数-存活株数)/试材总株数×100％
除草剂对植株的毒力级别根据以上公式算得的鲜重抑制率及死亡率数据，分为A、B、C、D四个等级：
A级 90％以上；B级 70-90％；C级 50-70％；D级 50％。
本发明系列化合物分别以200g/ha的施用量进行芽期土壤处理后，植株的鲜重抑制毒力效果见表2；1000g/ha的施用量进行芽后茎叶处理后，植株的鲜重抑制毒力效果见表3；化合物I-8芽期土壤处理中不同施用量所产生的毒力效果见表4。
表 2芽期土壤处理
| 样品 | 剂量 | 苘麻 | 反枝苋 | 藜 | 稗草 | 马唐 | 狗尾 |
| I-1 | 200g/ha | D | D | D | D | D | D |
| I-2 | 200g/ha | D | D | C | C | CD | CD |
| I-3 | 200g/ha | D | D | D | D | D | D |
| I-4 | 200g/ha | D | D | D | D | D | D |
| I-5 | 200g/ha | D | D | D | D | D | D |
| I-8 | 200g/ha | D | A | A | A | A | A |
| I-10 | 200g/ha | D | A | A | A | A | A |
| I-11 | 200g/ha | D | A | A | A | A | A |
| I-13 | 200g/ha | D | D | D | D | D | D |
| I-15 | 200g/ha | D | D | D | D | D | D |
| I-16 | 200g/ha | D | D | D | B | A | A |
| I-17 | 200g/ha | D | D | D | D | D | D |
表3 芽后茎叶处理
| 样品 | 剂量 | 苘麻 | 反枝苋 | 藜 | 稗草 | 马唐 | 狗尾 |
| I-1 | 1000g/ha | -- | -- | -- | -- | -- | -- |
| I-2 | 1000g/ha | BC | D | D | B | D | C |
| I-3 | 1000g/ha | D | D | D | D | D | D |
| I-4 | 1000g/ha | D | D | D | D | D | D |
| I-5 | 1000g/ha | D | D | D | D | D | D |
| I-8 | 1000g/ha | D | B | C | A | A | A |
| I-10 | 1000g/ha | D | D | CD | D | D | B |
| I-11 | 1000g/ha | D | D | D | A | B | B |
| I-13 | 1000g/ha | D | D | D | D | D | D |
| I-15 | 1000g/ha | D | D | D | D | D | D |
| I-16 | 1000g/ha | -- | -- | -- | -- | -- | -- |
| I-17 | 1000g/ha | -- | -- | -- | -- | -- | -- |
表4 化合物I-8芽期不同剂量土壤处理
| 样品 | 浓度(g/ha) | 苘麻 | 反枝苋 | 小藜 | 稗草 | 马唐 | 狗尾 |
| I-8 | 200 | D | A | A | A | A | A |
| 100 | D | B | -- | A | A | A | |
| 50 | D | B | C | B | A | A | |
| 25 | D | C | -- | D | C | A | |
| 苯噻草胺 | 200 | D | D | D | D | D | D |
| 100 | D | D | D | D | D | D | |
| 50 | D | D | D | D | D | D | |
| 25 | D | D | D | D | D | D |
实施例7：
作物安全性试验
以玉米、小麦、水稻为试材，按实施例三的方法进行盆栽试验，处理叶期为3-4叶期，并计算抑制率。化合物I-8与苯噻草胺作物安全性测试比较结果见表5。
表5 作物安全性试验
注：+表示测试化合物对试材有促进生长作用。
| 样品 | 浓度(g/ha) | 玉米抑制率(％) | 水稻抑制率(％) |
| I-8 | 800 | 5.3 | 3.5 |
| 200 | +14.1 | +13.2 | |
| 本噻草胺 | 800 | 3.5 | 2.8 |
| 200 | +12.1 | +6.3 |
从表2、表3、表4可见，I-2、I-8、I-10、I-11、I-16显示出明显土壤处理活性，I-2、I-8、I-10、I-11显示出明显茎叶处理活性，同一样品芽期土壤处理除草活性高于芽后茎叶处理，与苯噻草胺相比，I-8显示出明显的更好的活性。从表4可见，本发明活性化合物在50g/ha的低剂量下施用时，仍对禾本科杂草马唐、狗尾具有极好的防效，而对稗草、反枝苋、藜的毒力稍有减小，可见本发明化合物在低剂量施用时对禾本科杂草及某些阔叶杂草具有较好的防除活性。从表5可见，本发明化合物在高剂量施用时对玉米、水稻3-4叶期表现为安全。
Claims (5)
1、通式(I)除草的杂环基氧乙酰替苯胺类化合物，
其中，n代表1、2、或3；R1代表一直链或支链的烷基、链烯基、链炔基，或一被卤原子、氰基取代的直链或支链的烷基、链烯基、链炔基；R2代表烷基、烷氧基、硝基、氰基；或氟、氯、溴、碘元素，或卤代烷基；Het代表一可任意地被氟、氯、溴、碘、甲基、乙基、异丙基、三氟甲基、二氟甲基、一氯二氟甲基、二氯二氟甲基、甲硫基、乙硫基、苯基或卤代苯基取代的1，2，4-噻二唑基、1，3，4-噻二唑基，或可任意地被氟、氯、溴、碘、三氟甲基、二氟甲基、甲基、甲氧基取代的苯并噻唑基、或喹喔啉基或嘧啶基。
2、如权利要求1所述的除草的杂环基氧乙酰替取代苯胺类化合物，其特征在于通式(I)中，n代表1、2或3；R1代表甲基、乙基、异丙基；R2代表氟、氯、溴、甲基；Het代表1，3，4-噻二唑基、苯并噻唑基；或被氯原子取代的喹喔啉基；或被甲氧基取代的2，6-嘧啶基。
3、一种如权利要求1通式(I)的化合物的制备方法，其特征在于，在一定条件下，经由通式(II)的杂环化合物与通式(III)的N-烷基-N-取代苯基羟基乙酰胺类化合物反应，
Het-X (II)其中，Het代表的意义如权利要求1所述；X代表卤素原子或烷基磺酰基；
其中n、R1、R2代表的意义如权利要求1所述。
4、一种除草剂组合物，其特征在于含有至少一种如权利要求1中所述的通式(I)的化合物作为有效成分。
5、如权利要求4所述的除草剂组合物，其特征在于它为液态或固态，并含重量百分比为0.01-90％的通式(I)的化合物。
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