CN1153515A - N-杂环基-杂芳氧基乙酰胺 - Google Patents
N-杂环基-杂芳氧基乙酰胺 Download PDFInfo
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- CN1153515A CN1153515A CN 95194268 CN95194268A CN1153515A CN 1153515 A CN1153515 A CN 1153515A CN 95194268 CN95194268 CN 95194268 CN 95194268 A CN95194268 A CN 95194268A CN 1153515 A CN1153515 A CN 1153515A
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Abstract
本发明涉及通式(I)的新型的N-杂环基-杂芳氧基乙酰胺,以及制备该新型化合物的方法和中间物及其作为除草剂的用途。其中,R表示氢或各自任选取代的烷基、烯基、炔基或芳烷基,Het1表示任选苯稠合的和任选取代的杂芳基,和Het2表示任选取代的单环或双环杂环基,(但除化合物2-(2-苯并噻唑基氧基)-N-(4-吗啉基)-乙酰胺之外)。
Description
本发明涉及新型的N-杂环基-杂芳氧基乙酰胺,制备它们的方法和新型中间物,及其作为除草剂的用途。
已知某些N-杂环基-杂芳氧基乙酰胺(参见DE-A(德国公开说明书)2903966/US专利4509971;JP-A(日本公开说明书)03081269-引自Chem.Abstracts 115:92307Z;JP-A(日本公开说明书)05112547引自Chem.Abstracts 119:88927S)。然而这些化合物作为农业化学活性化合物还没有获得重视。
R为氢或各自任选取代的烷基、烯基、炔基或芳烷基,
Het1表示任选苯稠合的和任选取代的杂芳基,和
Het2表示任选取代的单环或双环杂环基,但放弃化合物2-(2-苯并噻唑基氧基)-N-(4-吗啉基)-乙酰胺(已见于DE-A(德国公开说明书)2903966/US Patent(美国专利)4509971)。
本发明还提供一种制备通式(I)的新型N-杂环基-杂芳氧基乙酰胺的方法:任选在稀释剂存在下和任选在反应助剂存在下使通式(II)的取代的杂芳烯(hetarene)与通式(III)的羟基乙酰胺反应,
最后,发现通式(I)的新型N-杂环基-杂芳氧基乙酰胺具有令人感兴趣的除草性能。
本发明优选提供通式(I)的化合物,其中
R表示氢、C1-C8-烷基(任选由氟、氯、氰基或C1-C8-烷氧基取代)、C2-C8-烯基(任选由氟和/或氯取代)、C2-C8-炔基或苄基(任选由氟、氯、氰基、C1-C4-烷基或C1-C4-烷氧基取代),
Het1表示任选苯稠合的和任选取代的五员杂芳基,选自噁唑基、异噁唑基、噻唑基、异噻唑基、苯并噁唑基、苯并噻唑基、噁二唑基和噻二唑基、可能的取代基优选选自氟、氯、溴、氰基、(各自任选由氟和/或氯取代的)C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C1-C6-烷氧基、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C3-C6-环烷基、苯基、吡啶基、呋喃基或噻吩基、和
Het2表示任选取代的单环或双环杂环基,选自呋喃基、苯并呋喃基、四氢呋喃基、吡咯基、苯并吡咯基、四氢吡咯基、噁唑基、异噁唑基、噻唑基、异噻唑基、噁二唑基、噻二唑基、吡啶基、喹啉基、四氢喹啉基、嘧啶基、三嗪基和四氢吡喃基、可能的取代基优选选自氟、氯、溴、氰基、(各自任选由氟-和/或氯-取代的)C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C1-C6-烷氧基、C1-C6-烷硫基、C1-C6-烷基亚磺酰基和C1-C6-烷基磺酰基。
本发明特别是涉及通式(I)的化合物,其中
R表示氢、甲基、乙基、正-或异-丙基、正-、异-、仲-或叔-丁基(各自任选由氟、氯、氰基、甲氧基或乙氧基取代)、丙烯基或丁烯基(各自任选由氟和/或氯取代)、丙炔基或丁炔基、或苄基(任选由氟、氯、氰基、甲基、乙基、甲氧基或乙氧基取代),
Het1表示任选苯稠合的和任选取代的五员杂芳基,选自噁唑-2-基、噻唑-2-基、苯并噁唑-2-基、苯并噻唑-2-基、1,2,4-噻二唑-5-基和1,3,4-噻二唑-2-基,可能的取代基优选选自氟、氯、溴、氰基,(各自任选由氟-和/或氯-取代的)甲基、乙基、正-或异-丙基、正-、异-、仲-或叔-丁基、甲氧基、乙氧基、正-或异-丙氧基、甲硫基、乙硫基、正-或异-丙硫基、甲基亚磺酰基、乙基亚磺酰基、正-或异-丙基亚磺酰基、甲基磺酰基、乙基磺酰基、正-或异-丙基磺酰基,和
Het2表示任选取代的单环或双环杂环基,选自呋喃基、苯并呋喃基、四氢呋喃基、噁唑基、异噁唑基、噻唑基、异噻唑基、噁二唑基、噻二唑基、吡啶基、喹啉基、四氢喹啉基、嘧啶基、三嗪基和四氢吡喃基、其中可能的取代基优选选自氟、氯、溴、氰基、(各自任选由氟-和/或氯-取代的)甲基、乙基、正-或异-丙基、正-、异-、仲-或叔-丁基、丙烯基、丁烯基、丙炔基、丁炔基、甲氧基、乙氧基、正-或异-丙氧基、甲硫基、乙硫基、正-或异-丙硫基、甲基亚磺酰基、乙基亚磺酰基、正-或异-丙基亚磺酰基、甲基磺酰基、乙基磺酰基、正-或异-丙基磺酰基。
本发明通式(I)化合物的特别优选的基团包括那些基团:其中R和Het1具有上述特别优选的含义和Het2表示呋喃基或噻吩基(特别是噻吩基)。
各基团的上述一般或特别的定义适合于通式(I)的最终产物,并相应地适合于各制备过程所需的起始原料或中间体。各基团的这些定义可以以任何方式互相结合,因此也在所述的优选化合物之列。
在本发明的方法中,制备通式(I)的化合物时需用作起始原料的取代的杂芳烯以通式(II)的通用形式定义。通式(II)中,Het1优选或特别具有,在前面描述通式(I)的化合物时指明的Het1的优选或特别优选的意义;X优选表示氟、氯、溴、C1-C4-烷硫基、C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基,特别是氯或甲基磺酰基。
通式(II)的起始原料是已知的和/或可按照已知的方法(参见J.Org.Chem.27(1962),2589-2592;EP-A(欧洲公开说明书)18497;EP-A(欧洲公开说明书)165 537;EP-A(欧洲公开说明书)308 740;EP-A(欧洲公开说明书)348 735;EP-A(欧洲公开说明书)348 737)制备。
在本发明的方法中,用作起始原料的羟基乙酰胺以通式(III)的通用形式定义。通式(III)中,R和Het2优选或特别具有在前面描述通式(I)的化合物时指明的R和Het2的优选或特别优选定义。
通式(III)的起始原料是已知的和/或可按照已知的方法(BE-A(比利时公开说明书)897 675;DE-A(德国公开说明书)3 303 388;DE-A(德国公开说明书)3 331 873;EP-A(欧洲公开说明书)181018;GB2114 566)制备。
从文献中尚未发现有通式(III)的化合物,其中R表示甲基、乙基、正-或异-丙基、正-、异-、仲-或叔-丁基,Het2表示噻吩基。
这些化合物(IIIa)是新的,也构成本申请主题的组成部分。
通式(III)的羟基乙酰胺由通式(IV)的乙酰氧基乙酰胺其中R和Het2具有前述意义与碱金属氢氧化物例如氢氧化钠或氢氧化钾,在稀释剂,例如水甲醇和/或乙醇存在下,在0℃至50℃之间反应,并按照常规的方式进行处理(参见制备实施例)而制得。
通式(IV)的中间物由对应的通式(V)的氨基杂环其中,R和Het2具有前述的含义与乙酰氧基乙酰氯任选在反应助剂,例如吡啶存在下,在0℃至30℃之间反应并按照常规的方式进行后处理(参见制备实施例)而制得。
作为中间物所需的通式(V)的氨基杂环是已知的和/或可按照已知的方法(Bull.Soc.Chem.France 1986,259-266)制备。
适宜用于实施本发明方法的稀释剂为常规的有机溶剂。特别是脂族、脂环族或芳香族、任选卤代的烃类,例如,挥发油、苯、甲苯、二甲苯、氯苯、二氯苯、石油醚、己烷、环己烷、二氯甲烷、氯仿、四氯化碳;醚类,例如二乙醚、二异丙醚、二噁烷、四氢呋喃或乙二醇二甲基或二乙基醚;酮类,例如,丙酮、丁酮或甲基异丁基酮;腈类,例如,乙腈、丙腈或苄腈;酰胺类,例如,N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基-吡咯烷酮或六甲基磷酰胺;酯类,例如,乙酸甲酯或乙酸乙酯;亚砜类,例如二甲基亚砜;醇类,例如甲醇、乙醇、正-或异-丙醇、乙二醇单甲醚、乙二醇单乙醚、二乙二醇单甲醚、二乙二醇单乙醚、及其与水的混合物或纯水。
本发明的方法优选在适宜的反应助剂存在下进行。适宜的反应助剂包括所有的常规无机的或三级(tertiary)有机碱。这些碱包括:例如碱金属或碱土金属的氢化物、氢氧化物、氨化物、醇化物、乙酸盐、碳酸盐或碳酸氢盐,例如,锂、钠、钾或钙的氢化物、锂、钠或钾的氨化物、钠或钾的甲醇盐、钠或钾的乙醇盐、钠或钾的丙醇盐、铝的异丙醇盐、钠或钾的叔丁醇盐、钠或钾的氢氧化物、铵的氢氧化物、钠、钾或钙的乙酸盐、铵的乙酸盐、钠、钾或钙的碳酸盐、铵的碳酸盐、钠或钾的碳酸氢盐,以及碱性有机氮化物,例如三甲胺、三乙胺、三丙胺、三丁胺、乙基二异丙基胺、N,N-二甲基环己胺、二环己胺、乙基-二环己基胺、N,N-二甲基苯胺、N,N-二甲基苯甲胺、吡啶、2-甲基-、3-甲基-和4-甲基吡啶、2,4-甲基-、2,6-二甲基、3,4-二甲基-和3,5-二甲基-吡啶、5-乙基-2-甲基-吡啶、N-甲基哌啶、N,N-二甲氨基吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DBN)或二氮杂双环十一碳烯(DBU)。
在实施本发明的方法时,反应温度可在一个相当宽的范围内变化。一般而言,反应在-50℃至100℃之间温度进行,优选在-30℃至60℃之间进行,特别是在-20℃至+20℃之间进行。
本发明的方法一般在大气压下进行,但它还可在升高或降低的压力下,一般0.1巴至10巴之间进行。
实施本发明方法所需的起始原料一般各自采用大约等摩尔的量。但,还可使各种情况下所用的两种化合物之一大大过量。反应一般在反应助剂存在下,在适宜的稀释剂中进行,反应混合物在各自所需的温度下搅拌数小时。本发明方法的后处理各自按照常规方法(参见制备实施例)进行。
本发明的活性化合物可用作脱叶剂、干燥剂、除茎叶剂,特别是用作除草剂。杂草在最广泛的意义上被认为是在不需要它们的地方生长的所有植物。本发明的物质是用于除去所有的杂草还是用作选择除草剂,这主要取决于用量。
本发明的活性化合物可用于诸如下列植物:
以下各属双子叶杂草:芸苔属、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、苋属、马齿苋属、齿苋属、苍耳属、旋花属、番诸属、蓼属、田菁属、豚草属、蓟属、飞廉属、苦苣菜属、茄属、焊菜属、水松叶属、母草属、野芝麻属、婆婆纳属、茼麻属、刺酸模属、曼陀罗属、堇菜属、鼬瓣花属、罂粟属、矢车菊属、三叶草属、毛莨属和蒲公英属。
以下各属双子叶栽培作物:棉属、大豆属、菾菜属、胡罗卜属、菜豆属、豌豆属、茄属、亚麻属、番薯属、巢菜属、菸草属、番茄属、花生属、荨菜属、莴苣属、黄瓜属和南瓜属。
以下各属单子叶杂草: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、慈姑属、荸荠属、藨草属、雀稗属、鸭嘴草属、尖瓣花属、龙爪茅属、翦股颖属、看麦娘属和野豚鼠草属(Apera)。
以下各属单子叶栽培作物:稻属、玉蜀黍属、小麦属、大麦属、燕麦属、黑麦属、蜀黍属、黍属、甘蔗属、凤梨属、天门冬属和葱属。
然而,本发明活性化合物的用途绝不仅限于以上各属,而也以同样的方式扩展到其它植物。
因浓度而异,这类化合物适合于诸如工业场地和铁路线上以及有或无树林的道路或广场上的灭生性除草。同样,这类化合物也可用于多年生栽培植物如造林、装饰性园林、果树园、葡萄园、桔园、坚果园、香焦园、咖啡园、茶园、橡胶园、油棕园、可可园、软果园和酒花田除草、草坪和牧场除草,以及一年生栽培植物的选择性除草。
本发明通式(I)的化合物特别适合于选择性控制双子叶作物中的单子叶杂草,特别用于出苗前处理。
活性化合物可以调制成常规的制剂,例如溶液、乳液、可湿性粉剂、悬浮液、粉末、尘剂、糊剂、可溶性颗粒剂、粒剂、悬浮液浓液、浸泡活性化合物的天然或合成材料,在高分子物质中的细小囊剂。
这些制剂用已知方法制成,例如通过下述方法:活性化合物和稀释剂,即液体溶剂和/或固体载体,任意使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂混合。
如果采用水作为稀释剂,则也可用例如有机溶剂作助溶剂。适用的液体溶剂主要有: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肪烃,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、矿物油和植物油;醇,如丁醇或乙二醇,以及它们的醚和酯;酮,如丙酮、甲乙酮、甲基异丁基酮或环己酮;强极性溶剂如二甲基甲酰胺和二甲基亚砜以及水。
适用的固体载体有:如铵盐和研碎的天然矿物,如高岭土、粘土、滑石粉、白垩、石英、绿坡缕石、蒙脱石或硅藻土,和研碎的合成矿物,如高分散度硅石、三氧化二铝和硅酸盐;适用的颗粒固体载体有:如粉碎并分级的天然矿石,例如方解石、大理石、浮石、海泡石和白云石,及合成的无机颗粒和有机粉,和有机材料颗粒,如锯末、椰子壳、玉米棒碎块和烟草杆;适用的乳化剂和/或起泡剂有:如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧化乙烯脂肪醇醚,例如烷芳基聚乙二醇醚、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐以及蛋白质水解产物;适用的分散剂有:如亚硫酸纸浆废液和甲基纤维素。
在制剂中可采用的粘合剂有:羧甲基纤维素和粉状、颗粒状或胶乳状的天然和合成聚合物,如阿拉伯树胶、聚乙烯醇,聚乙酸乙烯酯以及天然磷脂,如脑磷脂、卵磷脂和合成磷脂。其它可能的添加剂为矿物油和植物油。
可采用着色剂,如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,以及有机染料,如茜素染料、偶氮染料和金属酞菁染料,以及微量营养素,如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中一般含有0.1至95%(重量),优选0.5至90%的活性化合物。
本发明的活性化合物用作除草剂时,可直接或以制剂形式,也可与已知除草剂形成混合物使用;也可能是成品制剂或罐装的混合物。
可用于这类混合物的适宜除草剂有下述已知的除草剂,例如N-酰苯胺类,如二氟酚(diflufenican)和敌稗;芳基羧酸类,如二氯吡啶甲酸、麦草畏和毒莠定;芳氧基链烷酸类,如2,4-D(2,4-滴)、2,4-DB(2,4-滴丁酸)、2,4-DP(2,4-滴丙酸)、氟氧吡啶(fluroxypyr)、MCPA(2甲4氯)、MCPP(2甲4氯丙酸)和木草畏(triclopyr)、芳氧基-苯氧基链烷酸酯,如禾草灵(diclofop-methyl)、乙基酚丙酸(fenoxaprop-ethyl)、禾草枯(fluazifop-butyl)、甲基海酚丙(haloxyfop-methyl)和2-[4-[(6-氯-2-喹喔啉基)氧]苯氧基]丙酸乙酯(quizalofop-ethyl)、azinone类,例如5-氨基-4-氯-2-苯基哒嗪-3(2H)-酮(Chloridazon)和哒草灭;氨基甲酸酯类,例如氯苯胺灵、异苯敌、苯敌草和苯胺灵、氯乙酰替苯胺类,例如草不绿、灭草胺、去草胺、甲吡唑安(metazachlor)、甲代隆、氯苯胺和毒草胺;二硝基苯胺类,例如黄草消、芽草平和氟乐灵;二苯醚类,例如氟草灭、治草醚、氟糖酚(fluoroglycofen)、虎威、halosafen、乳酚(lactofen)和氟草胺;脲类,例如绿麦隆、敌草隆、伏草隆、异丙隆、利谷隆和噻唑隆;羟胺类,例如枯杀达、乙氧定(clethodim)、环氧定(cycloxydim)、禾莠净和烷氧定(tralkoxydim);咪唑啉酮类,例如咪唑乙畏(imazethapyr)、咪唑甲苯(imazamethabenz)、咪唑吡啶(imazapyr)和咪唑喹啉(imazaquin);腈类,例如溴苯腈、敌草腈和碘苯腈;氧乙酰胺类,例如mefenacet;磺酰脲类,例如amidosulfuron、甲基苯磺隆(bensulfuron-methyl)、乙基氯默隆(chlorimuron-ethyl)、阔草脲、cinosulfuron、甲基甲磺隆(metsulfuron-methyl)、nicosulfuron、primisulfuron、乙基吡唑杀隆(pyrazosulfuron-ethyl)、甲基西酚杀隆(thifensulfuron-methyl)、三硫隆(triasulfuron)和甲基三苯隆(tribenuron-methyl);硫代氨基甲酸酯类,例如苏达灭、草灭特、燕麦敌、扑草灭、esprocarb、草达灭、扑硫威(prosulfocarb)、杀草丹和野麦畏;三嗪类,例如阿特拉津、草争津、西玛津、西草净、去草净和特丁津(terbutylazine);三嗪酮类,例如敌草灵(hexazinone)、灭它通(metamitron)和赛克津;及其它除草剂,例如氨基三唑、benfuresate、噻草平、辛甲灵(cinmethylin)、氯马腙(clomazone)、氯吡啶(clopyralid)、燕麦清(difenzoquat)、dithiopyr、草定完、卤吡咯酮(fluorochloridone)、glufosinate、草甘膦、异噁苯(isoxaben)、草利达(pyridate)、quinchlorac、quinmerac、sulphosate和环氧乙烷(tridiphane)。
与其它已知活性化合物如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物营养剂及土壤结构改良剂的混合物也可以使用。
活性化合物可以原药形式、其制剂形式、或通过进一步稀释例如可直接使用的溶液、悬浮液、乳液、粉剂、膏剂和颗粒剂而制备的使用形式加以使用,它们以浇水、喷雾、雾化或喷洒等习用方式使用。
本发明的活性化合物既可以在植物发芽前也可在植物发芽后施用,它们也可以在播种前混入土壤中。
活性化合物的用量可以在一个很大的范围内变化。这基本上取夹于预期效果的性质。一般地说,用量是每公顷土壤表面积为10克-10千克活性化合物,较好是50克-5千克/公顷。
本发明的活性化合物的制备和用途可从下述实施例中看出。制备实施例实施例1
将0.6克(3.5mmol)N-甲基-N-(2-噻吩基)-羟基乙酰胺与0.8克(3.5mmol)2-甲基磺酰基-5-三氟甲基-1,3,4-噻二唑和10ml丙酮一起加料,然后将该混合物冷却至-20℃。然后滴加0.17克氢氧化钠的2ml水溶液。将反应混合物在-15℃搅拌2小时,再在高至0℃的温度搅拌12小时。然后将混合物倾至两倍体积的水中,经抽滤分离所得的结晶产品。
得到熔点为46℃的N-甲基-N-(2-噻吩基)-2-(5-三氟甲基-1,3,4-噻二唑-2-基氧基)-乙酰胺。
实施例1的方法和本发明方法的一般要点可用于制备例如下述表1的式(I)的化合物表1:式(I)化合物示例实施例号 Het1 Het2 R 物理常数2
CH33
CH34
CH35
CH36
CH37
CH38
CH39
CH3实施例号 Het1 Het2 R 物理常数10
CH311
CH312
CH313
CH314
CH315
CH316
CH317
CH3实施例号 Het1 Het2 R 物理常数18
CH319
CH320
CH321
CH322
CH323
CH324
CH3实施例号Het1 Het2 R 物理常数25
CH3 熔点:80℃26
CH3 熔点:209℃27
CH3 熔点:153℃
在表1中的实施例26的化合物可适宜地制备如下,
将31.4克(0.15mol)2-(苯并噻唑-2-基氧基)乙酸加热溶于150ml四氢呋喃中。在60至65℃之间滴加16.5克(0.08mol)二环己基碳二亚胺于少量四氢呋喃中的溶液。继续搅拌2小时。排除湿气,然后蒸除四氢呋喃。然后向残渣中滴加8.6克(0.08mol)2-甲氨基吡啶于80ml四氢呋喃中的溶液。然后搅拌回流混合物2小时,冷却并浓缩。残渣用甲苯处理,甲苯溶液用碳酸氢钠水溶液萃取。有机相用硫酸钠干燥,过滤后,浓缩至四分之一体积。所需化合物以结晶形式沉淀,抽滤并用甲苯重结晶。
产量:.2.1克熔点为209℃的N-甲基-N-(2-吡啶基)-2-(苯并噻唑-2-基氧基)-乙酰胺。
表1中的实施例25和实施例27的化合物可以类似方式制得。式(III)的起始物实施例(III-1)
在-10℃,将0.55ml 45%氢氧化钠水溶液(6.6mmol NaOH)滴加到1.3克(6.0mmol)N-甲基-N-(2-噻吩基)-乙酰氧基乙酰胺溶于5ml甲醇中的溶液中,在20℃搅拌混合物5小时。然后用6滴浓盐酸酸化混合物,并用水泵真空浓缩。残渣用水/二氯甲烷振荡,分出有机相,用硫酸钠干燥并过滤。用水泵真空小心地从溶液中蒸去溶剂。
得到熔点为89℃的晶状残渣N-甲基-N-(2-噻吩基)-羟基乙酰胺。式(IV)的起始物实施例(IV-1)
在15ml浓盐酸中加热回流4.65克(0.03ml)N-甲基-N-(2-噻吩基)乙酰胺20分钟。冷却后,加入50ml二氯甲烷,在20℃将混合物与6.6克(0.150mol)氢氧化钠在20ml水中的溶液混合。再加入50ml二氯甲烷后,分出有机相,用硫酸钠干燥并过滤。滤液中含有2-(甲氨基)噻吩,与10.5克(0.132mol)吡啶混合,并在0~5℃之间滴加5.25克(0.038mol)乙酰氧基乙酰氯。然后在20℃搅拌混合物12小时。混合物进行后处理时,用水稀释,并用甲基叔丁基醚萃取。用水泵真空小心地蒸除甲基叔丁基醚。
得到熔点为52℃的结晶残渣状化合物N-甲基-N-(2-噻吩基)-乙酰氧基乙酰胺。
起始物N-甲基-N-(2-噻吩基)-乙酰胺的制备已见于文献〔参见Liebigs Ann.Chem.403卷,17-44页(1914)〕。
使用实例
实例A
出苗前试验
溶剂:5重量份丙酮
乳化剂:1重量份烷芳基聚二醇醚
为生产一种适用的活性化合物制剂,把1重量份活性化合物与所述量的溶剂混合,添加所述量的乳化剂,用水把这种浓制剂稀释到预期浓度。
把试验植物的种子播入标准土壤中,24小时后用该活性化合物的制剂浇水。方便的做法是使每单位面积的水量保持恒定。该制剂中活性化合物的浓度并不重要,只有每单位面积施用的活性化合物数量才是决定性的。3周后,与未处理的对照组的发育情况进行比较,用%损害率评定对植物的损害程度。数字表示为:
0%=无作用(与未处理对照组一样)
100%=完全毁坏
在本试验中,例如用实施例1的方法制备的活性化合物表现出很好的抗杂草性,而它又可为作物,例如甜菜,很好地耐受。表A1:出苗前试验/温室活性化合物 施用量 甜菜 看麦娘属 燕麦属 马唐属 毒麦属 早熟禾类
(g/公顷)(1) 500 0 100 90 95 100 100表A2:出苗前试验/温室活性化合物 施用量 看麦娘属 燕麦属 狗尾草属 苋属 芥子
4000 100 90 100 100 100(25)
Claims (10)
2.根据权利要求1的通式(I)的化合物,其特征在于
R表示氢、C1-C8-烷基(任选由氟、氯、氰基或C1-C8-烷氧基取代)、C2-C8-烯基(任选由氟和/或氯取代)、C2-C8-炔基或苄基(任选由氟、氯、氰基、C1-C4-烷基或C1-C4-烷氧基取代),
Het1表示任选苯稠合的和任选取代的五员杂芳基,选自噁唑基、异噁唑基、噻唑基、异噻唑基、苯并噁唑基、苯并噻唑基、噁二唑基和噻二唑基、可能的取代基优选选自氟、氯、溴、氰基、(各自任选由氟和/或氯取代的)C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C1-C6-烷氧基、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C3-C6-环烷基、苯基、吡啶基、呋喃基或噻吩基,和Het2表示任选取代的单环或双环杂环基,选自呋喃基、苯并呋喃基、四氢呋喃基、吡咯基、苯并吡咯基、四氢吡咯基、噁唑基、异噁唑基、噻唑基、异噻唑基、噁二唑基、噻二唑基、吡啶基、喹啉基、四氢喹啉基、嘧啶基、三嗪基和四氢吡喃基,可能的取代基优选选自氟、氯、溴、氰基、(各自任选由氟-和/或氯-取代的)C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C1-C6-烷氧基、C1-C6-烷硫基、C1-C6-烷基亚磺酰基和C1-C6-烷基磺酰基。
3.根据权利要求1的通式(I)化合物,其特征在于
R表示氢、甲基、乙基、正-或异-丙基、正-、异-、仲-或叔-丁基(各自任选由氟、氯、氰基、甲氧基或乙氧基取代)、丙烯基或丁烯基(各自任选由氟和/或氯取代)、丙炔基或丁炔基、或苄基(任选由氟、氯、氰基、甲基、乙基、甲氧基或乙氧基取代),
Het1表示任选苯稠合的和任选取代的五员杂芳基,选自噁唑-2-基、噻唑-2-基、苯并噁唑-2-基、苯并噻唑-2-基、1,2,4-噻二唑-5-基和1,3,4-噻二唑-2-基,可能的取代基优选选自氟、氯、溴、氰基,(各自任选由氟-和/或氯-取代的)甲基、乙基、正-或异-丙基、正-、异-、仲-或叔-丁基、甲氧基、乙氧基、正-或异-丙氧基、甲硫基、乙硫基、正-或异-丙硫基、甲基亚磺酰基、乙基亚磺酰基、正-或异-丙基亚磺酰基、甲基磺酰基、乙基磺酰基、正-或异-丙基磺酰基,和
Het2表示任选取代的单环或双环杂环基,选自呋喃基、苯并呋喃基、四氢呋喃基、噁唑基、异噁唑基、噻唑基、异噻唑基、噁二唑基、噻二唑基、吡啶基、喹啉基、四氢喹啉基、嘧啶基、三嗪基和四氢吡喃基,其中可能的取代基优选选自氟、氯、溴、氰基、(各自任选由氟-和/或氯-取代的)甲基、乙基、正-或异-丙基、正-、异-、仲-或叔-丁基、丙烯基、丁烯基、丙炔基、丁炔基、甲氧基、乙氧基、正-或异-丙氧基、甲硫基、乙硫基、正-或异-丙硫基、甲基亚磺酰基、乙基亚磺酰基、正-或异-丙基亚磺酰基、甲基磺酰基、乙基磺酰基、正-或异-丙基磺酰基。
4.根据权利要求3的通式(I)化合物,其特征在于
Het2表示呋喃基或噻吩基。
6.除草组合物,其特征在于至少含有一种权利要求1的通式(I)化合物。
7.权利要求1的通式(I)化合物用于控制不需要的植物生长的用途。
8.控制杂草的方法,其特征在于使权利要求1的通式(I)化合物作用于杂草或它们的环境。
9.除草组合物的制备方法,其特征在于将权利要求1的通式(I)化合物与稀释剂和/或表面活性剂混合。
10.通式(IIIa)的羟基乙酰胺其中,
R表示甲基、乙基、正-或异-丙基、正-异-、仲-或叔-丁基,和
Het2表示噻吩基。
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CN103596945A (zh) * | 2011-03-15 | 2014-02-19 | 拜耳知识产权有限责任公司 | N-(1,2,5-噁二唑-3-基)-、n-(四唑-5-基)-和n-(三唑-5-基)双环芳基-羧酰胺及其作为除草剂的用途 |
CN103694197A (zh) * | 2014-01-09 | 2014-04-02 | 华中师范大学 | 苯氧乙酰胺类化合物及其制备方法与应用 |
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CN103596945A (zh) * | 2011-03-15 | 2014-02-19 | 拜耳知识产权有限责任公司 | N-(1,2,5-噁二唑-3-基)-、n-(四唑-5-基)-和n-(三唑-5-基)双环芳基-羧酰胺及其作为除草剂的用途 |
CN103596945B (zh) * | 2011-03-15 | 2016-04-13 | 拜耳知识产权有限责任公司 | N-(1,2,5-噁二唑-3-基)-、n-(四唑-5-基)-和n-(三唑-5-基)双环芳基-羧酰胺及其作为除草剂的用途 |
CN103694197A (zh) * | 2014-01-09 | 2014-04-02 | 华中师范大学 | 苯氧乙酰胺类化合物及其制备方法与应用 |
CN103694197B (zh) * | 2014-01-09 | 2015-07-15 | 华中师范大学 | 苯氧乙酰胺类化合物及其制备方法与应用 |
CN106715403A (zh) * | 2014-07-28 | 2017-05-24 | 拜耳作物科学股份公司 | 二环芳基羧酸酰胺及其作为除草剂的用途 |
CN106715403B (zh) * | 2014-07-28 | 2020-06-02 | 拜耳作物科学股份公司 | 二环芳基羧酸酰胺及其作为除草剂的用途 |
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