CN1131668A - N-甲基-n-异丙基-杂芳氧基乙酰胺 - Google Patents
N-甲基-n-异丙基-杂芳氧基乙酰胺 Download PDFInfo
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- CN1131668A CN1131668A CN95120351A CN95120351A CN1131668A CN 1131668 A CN1131668 A CN 1131668A CN 95120351 A CN95120351 A CN 95120351A CN 95120351 A CN95120351 A CN 95120351A CN 1131668 A CN1131668 A CN 1131668A
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- 238000000034 method Methods 0.000 claims abstract description 19
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims abstract description 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims abstract description 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims abstract description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims abstract description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 42
- -1 4-thiadiazolyl group Chemical group 0.000 claims description 32
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- 238000006243 chemical reaction Methods 0.000 claims description 9
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
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- 229910052794 bromium Inorganic materials 0.000 claims description 3
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
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- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
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- 150000003751 zinc Chemical class 0.000 description 1
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Abstract
本发明涉及一种新的N-甲基-N-异丙基-杂芳氧基乙酰胺(I)、其制备方法和作为除草剂的用途。
(I)中Het代表选自噁唑基、异噁唑基、噻唑基、异噻唑基、苯并噁唑基、苯并噻唑基、1,2,4-噁二唑基、1,3,4-噁二唑基,1,2,4-噻二唑基和1,3,4-噻二唑基任选的苯并稠合和任意取代的杂芳基。
Description
本发明涉及新的N-甲基-N-异丙基-杂芳氧基乙酰胺,其制备方法和其作为除草剂的用途。
据了解某些N-甲基-N-异丙基-杂芳氧基乙酰胺,例如N-甲基-N-异丙基-2-(4-苯基-1,2,3-噻二唑-5-基-氧基)乙酰胺化合物具有除草性质(化学文摘115:92307Z中引述的JP-A03081269),然而,该已知化合物的活性,或者说这些已知化合物并非完全令人满意,特别是当活性化合物的使用比例及浓度低时更是如此。
业已发现具有下述通式(1)的新的N-甲基-N-异丙基-杂芳氧基乙酰胺:其中Het代表选自噁唑基、异噁唑基、噻唑基、异噻唑基、苯并噁唑基、苯并噻唑基、1,2,4-噁二唑基、1,3,4-噁二唑基、1,2,4-噻二唑基和1,3,4-噻二唑基的任选的苯并稠合和任意取代的杂芳基。
而且还发现,当下述(II)式代表的取代杂芳烃同(III)式代表的N-甲基-N-异丙基-羟基乙酰胺反应即可制得(1)式代表的N-甲基-N-异丙基-杂芳氧基乙酰胺,如果需要,此反应在稀释剂存在下进行,并且如果需要在反应助剂存在下进行,所说(II)为Het-X,Het的含义与上述相同,X为卤素、烷硫基、烷基亚硫酰基或烷基磺酰基;(III)式为:
还发现新的(I)式化合物N-甲基-N-异丙基-杂芳氧基乙酰胺具有好的除草性质。
本发明优选涉及其中的Het为从下述一组基团中选出的任选的苯并稠合和任意取代的杂芳基:噁唑基、异噁唑基、噻唑基、异噻唑基、苯并噁唑基、苯并噻唑基、1,2,4-噁二唑基、1,3,4-噁二唑基、1,2,4-噻二唑基和1,3,4-噻二唑基。所说取代基优选选自:卤素、氰基、(在每一情形下为任选氟-和/或氯-取代的)C1-C6烷基、C2-C6链烯基、C2-C6炔基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、C1-C6烷基磺酰基-甲基、C3-C6环烷基、苯基、苯氧基甲基、苄磺酰基、吡啶基、呋喃基或噻唑基。
本发明特别涉及其中的Het为从下述一组基团中选出的任选的苯并稠合和任意取代的杂芳基:1,3-噁唑-2-基、1,3-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。所说取代基可优选为下述一组基团中选出的基团:氟、氯、溴、氰基、(在每一情形下任选被氟和/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、甲基亚硫酰基、乙基亚硫酰基、正-或异丙基亚硫酰基、甲基磺酰基、乙基磺酰基、正-或异-丙基磺酰基、环丙基、环丁基、环戊基、环己基、苯基、吡啶基、呋喃基或噻吩基。
上述一般范围内或优选范围内基团的定义适用于(I)式代表的最终产品,同样也适用于每一情形下制备所需的起始物料或中间体,定义的这些基团可与所需要的基团彼此结合,即所定义的优选范围内的化合物间的结合也是可能的。
(II)式给出了用作根据本发明方法制备(I)式化合物的起始物料的取代的杂芳烃的一般定义。(II)式中的优选或特别优选的Het的定义和前面介绍(I)式化合物中的优选或特别优选的Het的定义相同;X优选为氟、氯、溴、C1-C4烷硫基、C1-C4烷基亚硫酰基或C1-C4烷基磺酰基,特别优选氯或甲基磺酰基。
起始物料(II)是已知的或可用已知方法来制备(参见J.Org.Chem.27(1962),2589-2592;EP-A 5501;EP-A 18497;EP-A165537;EP-A 308740;EP-A 348735;EP-A 348737)。
在本发明方法中用作起始物料的(III)式化合物N-甲基-N-异丙基-羟基乙酰胺早已被披露(参见,EP-A 5501,EP-A 18497;制备实施例)。
适宜于实施本发明方法的稀释剂是惯常的有机溶剂。它们包括脂族的、脂环的或芳族的、任选卤代的烃,如戊烷、己烷、庚烷、石油醚、粗汽油、汽油、苯、甲苯、二甲苯、氯代苯、二氯代苯、环己烷、甲基己烷、二氯甲烷、氯仿、四氯甲烷;醚,如乙醚、二异丙醚、叔-丁甲醚、叔-戊甲醚、二噁烷、四氢呋喃、乙二醇二甲醚或乙二醇二乙醚、二甘醇二甲醚或二甘醇二乙醚;酮类,如丙酮、丁酮、甲异丙酮或甲异丁酮;腈类,如乙腈、丙腈、丁腈或苄腈;酰胺类,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三胺;酯类,如乙酸甲酯、乙酸乙酯、乙酸正或异丙酯、乙酸正-、异-或仲-丁酯,亚砜类,如二甲基亚砜;醇类,如甲醇、乙醇、正或异丙醇、正-、异-、仲-或叔-丁醇、乙二醇单甲醚或乙二醇单乙醚、二甘醇甲醚、二甘醇-乙醚;上述稀释剂与水的混合物,或纯水。
根据本发明的方法优选在适宜的反应助剂存在下进行。所有惯常的有机或无机碱均是可能的反应助剂。这些助剂包括碱金属或碱土金属的氢化物、氢氧化物、氨化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐,例如,氢化锂、氢化钠、氢化钾或氢化钙,氨基化锂、氨基化钠或氨基化钾,甲醇钠或甲醇钾、乙醇钠或乙醇钾、丙醇钠或丙醇钾、异丙醇铝、叔-丁醇钠或叔-丁醇钾、氢氧化钠或氢氧化钾、乙酸钠、乙酸钾或乙酸钙、乙酸铵、碳酸钠、碳酸钾或碳酸钙、碳酸铵、碳酸氢钠或碳酸氢钾,碱性有机氮化合物,如三甲胺、三乙胺、三丙胺、三丁胺、乙基-二异丙胺、N,N-二甲基环己胺、二环己胺、乙基-二环己胺、N,N-二甲基苯胺、N,N-二甲基苄胺、吡啶、2-甲基-、3-甲基-和4-甲基吡啶、2,4-二甲基-、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-二甲基氨基吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBN)或二氮杂二环十一烯(DBU)。
实施本发明方法的反应温度可在一较大范围内变化。一般为-50℃至+150℃,优选-30℃至+100℃,特别优选-10℃至+50℃。
一般讲,可在大气压下进行本发明的方法。然而,也可在升或减压下进行,压力一般为0.1-10巴。
进行本发明方法时每一情形下所需的起始物料一般为等摩尔左右。然而在每一情况下两种化合物中的一种化合物的量也可大于另一种化合物的量。一般讲此反应在反应助剂存在的适宜稀释剂中进行,在每一情形下在所需的反应温度下搅拌此反应混合物几小时。按惯常方法来进行本发明的方法(参见制备例)。
根据本发明的活性化合物可用作杀阔叶植物的落叶剂和干燥剂,特别是用作除草剂。广义上讲,杂草应理解为不需要其生长的地方的所有植物。然而本发明物质是作为令除草剂还是选择性除草剂主要取决于用量。
根据本发明的活性化合物可用于下面有关的植物。
下列属的双子叶杂草:欧白芥、独行菜、拉拉藤、繁缕、母萄、春黄萄、牛藤萄、藜、荨麻、千里光、苋、马齿苋、苍耳、旋花、番薯、蓼、田菁、豚草、蓟、飞廉、苦苣菜、茄、焊菜、节节菜、母草、野生芝麻、婆婆纳、苘麻、刺酸模、曼陀罗、堇菜、鼬瓣花、罂粟和矢车萄。
下列属的双子叶作物:棉、大豆、甜菜、胡罗卜、菜豆、豌豆、茄、亚麻、番薯、野豌豆、烟草、番茄、落花生、芸苔、莴苣、香瓜和南瓜。
下列属的单子叶杂草:稗、狗尾草、黍、马唐、梯枚草、早熟禾、羊茅、参、臂形草、黑麦草、雀麦、燕麦、莎草、高粱、水草、狗牙根、寸久花、飘拂草、慈菇、荸荠、蔗草、雀稗、鸭嘴草、尖瓣花、龙爪茅、剪股颖、看麦娘和风草。
下列属的单子叶作物:稻、玉蜀黍、小麦、大麦、燕麦、黑麦、高粱、黍、甘蔗、风梨、天门冬和葱。
但是,根据本发明的活性化合物决不仅限于用于上述属的植物,同样也可用于其他植物。
根据所应用的浓度,本发明的化合物适用于防治全部杂草,例如除去工业区和铁路线上的杂草,以及栽有或未栽树木的小路和广场区的杂草。同样,本发明化合物可用于防治多年生作物中的杂草,例如造林、观赏树林的栽培、果园、葡萄园、柑桔园、坚果园、香蕉种植园、咖啡种植园、茶场、橡胶种植园、油棕种植园、可可种植园、小果种植园和蛇麻草田中的杂草,并且本发明化合物还可以用于选择性防治一年生作物中的杂草。
根据本发明的(I)式化合物特别适用于用于芽前施药方法有选择地除去单和双子叶作物中的单和双子叶杂草。
此外,化合物(I)还有一些杀虫作用,如对寄生在叶上的昆虫、对真菌、如水稻的稻疫病有防治作用。
可将所说活性化合物配制成惯常的制剂,如溶液、浮剂、可湿性粉剂、悬浮剂、粉剂、撒粉剂、糊剂、可溶性粉剂、粒剂、悬浮-乳油浓缩液,浸渍有活性成分的天然或合成物质及外层为聚合物的极细胶囊。
可用已知方法来制备这些制剂,例如与增量剂,即液体溶液和/或固体载体混合,任选地与使用的表面活性剂,即浮化剂和/或分散剂和/或起泡剂混合。
如用水作增量剂,可用如有机溶剂作助溶剂。作为液体溶剂,适宜的主要有如二甲苯、甲苯或烷基萘、氯代芳族及氯代脂族烃,如氯苯、氯乙烯或二氯甲烷、脂族烃,如环己烷或链烷烃,如石油馏份、矿物及植物油、醇类,如丁醇或乙二醇及其醚和酯,酮类,如丙酮、甲乙酮、甲异丁酮或环己酮、强极性溶剂,如二甲基甲酰胺和二甲基亚砜,及水。
作为适宜的固体载体的例子有:铵盐和粉状天然矿物,如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱土或硅藻土及粉状合成矿物,如高度分散氧化硅、氧化镁和硅酸盐,粒剂用的适宜固体载体有如粉碎和分散的天然矿石、如方解石、大理石、浮石、海泡石和白云石,和合成无机和有机粗粉,和有机材料颗粒、如锯木屑、椰子壳、玉米蕊和烟草茎;作为适宜的乳化和/或起泡剂的有如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯类、聚氧乙烯脂肪醇醚,如烷基芳基聚乙二醇醚、烷基磺酸盐、硫酸烷基盐、芳基磺酸盐及蛋清水解产物;作为适宜的分散剂的有如木质亚硫酸盐废液和甲基纤维素。
用于制剂中的粘合剂,如羧甲基纤维素及粉状、粒状或乳胶状的天然和合成聚合物,如阿拉伯树胶、聚乙烯醇和聚乙烯乙酸酯和天然磷脂,如脑磷脂和卵磷脂、和合成磷脂。矿物油和植物油也可作添加剂。
也可使用着色剂,如无机颜粒,如氧化铁、氧化钛和普鲁士蓝及有机染料,如茜素染料、偶氮染料和金属酞菁及微量营养素,如金属盐,如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
重量计,制剂中一般活性成分0.1-95%,优选0.5-90%。
为了防治杂草,本发明的活性化合物本身或以制剂形式可与已知的除草剂、成品制剂或罐混合物形成混合物的形式来使用。
作混合物的已知除草剂有如酰替苯胺类,如diflufenican和敌稗;芳基羧酸,如二氯吡啶甲酸、麦草畏和毒莠定;芳氧基链烷酸,如2,4-二氯苯乙酸、2,4-滴丁酸、2,4-滴丙酸、fluroxypyr、2甲4氯苯乙酸、2甲4氯丙酸和乙氯草定、芳氧基-苯氧基链烷酸酯,如diclofop-methyl、fenoxaprop-ethyl、fluazifop-butyl、haloxyfop-methyl和quizalofop-ethyl;azinones,如氯哒酮和氟哒酮;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,草不绿、乙基、乙草安、去草安、metazachlor、甲氧毒草安、pretilachlor、和氟乐灵;二硝基苯胺类,如oryzalin,pendimethalin和trifluralin;苯醚类,如acifluorfen、甲酯除草醚、fluoroglycofen、fomesafen、halosafen、lactofen和乙氧氟甲草醚;脲类,如,绿麦隆、敌草隆、伏草隆、异丙隆、利谷隆和噻唑隆;羟胺类,如alloxydim、clethodim、sethoxydim和tralkoxydim;咪唑啉酮类,如imazethapyr、imazamethabenz、imazapyr和imazaquin;腈类,如溴草腈、敌草腈和4-羟-3,5-二碘苯甲腈;羟乙酰胺类,如mefenacet;磺酰脲类,如amidosulfuron、bensulfuron-methyl、chlorimuron-ethyl、chlorsulfuron、cinosulfuron、metsulfuron-methyl、nicosulfuron、primisulfuron、pyrazosulfuron-ethyl、thifensulfuron-methyl、triasnlfuron和tribenuron-methyl;硫代氨基甲酸酯类,如异丁草丹、环己丹、二氯烯丹、丙草丹、esprocarb、环草丹、prosulfocarb、thiobencarb和三氯烯丹;敌菌灵类,如阿特拉津、丙腈津、丁马津、西玛净、特丁草净和特定净;triazinones,如hexazinone、苯甲嗪和赛克嗪;其他除草剂,如氨基三唑,如benfuresate、苯达松、cinmethylin、clomazone、clopyralid、草吡唑、dithiopyr、甜苯呋、fluorochloridone、g1ufosinate、草甘膦、isoxaben、pyridate、quinchlorac、quinmerac磺酸盐(或酯)和tridiphane。
也可是与其他已知活性化合物的混合物,这些其它活性化合物如杀真菌剂、杀昆虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物营养素和改进土壤结构的试剂。
活性化合物本身,可以其制剂的形式或通过进一步稀释来制备的使用形式,如将使用的溶液剂、悬浮剂、乳剂、粉剂、糊剂和粒剂来使用。可按惯常的方式来使用这些活性化活物,如洒水的办法,喷雾的办法,雾化或分散办法使用这些活性化合物。
既可在芽前也可在芽后使用根据本发明的活性化合物,也可在播种前施于土壤中。
所使用的活性化合物的量可在一大范围内变化。这主要取决于所希望达到的效果的性质。一般而言,所用的活性成份的量为每公顷土壤面积10克-10公斤,优选每公顷土壤表面50克-5公斤。
从下述实施例中可以了解到本发明的活性化合物的制备方法和使用方法。制备实施例
于0-5℃,向搅拌的由2.7g(20mmol)N-甲基-N-异丙基-羟基乙酰胺、2.2g(20mmol)叔-丁醇钾、15ml乙腈和50ml叔-丁醇组成的混合物中加入3.0g(20mmol)2-氯-苯并噁唑。将此反应混合物20℃下搅拌12小时后,随后缓慢用水稀释到约其体积的两倍,然后用冰冷却。抽吸过滤分离此法获得的晶状产品。
得到4.0g(理论值的82%)N-甲基-N-异丙基-2-(苯并噁唑-2-基-氧基)乙酰胺,熔点56℃。
下表1中列出了按类似于实施例1的方法和所介绍的本发明的一般方法制的化合物(I)的其它例子。
表1:化合物(I)的例子例号 Het 物理数据2
nD 20=1.46623
m.p.:74℃4
m.p.:106℃5
m.p.:98℃6
nD 20=1.49027
nD 20=1.48728
nD 20=1.47929
m.p.:75℃
表1(续)例号 Het 物理数据10
nD 20=1.528811
nD 20=1.519212
(oil)13
nD 20=1.507514
m.p.:90℃15
m.p.:76℃16
nD 20=1.438017
m.p.:85℃
表1(续)例号 Het 物理数据18
nD 20=1.509919
nD 20=1.488520
nD 20=1.466521
nD 20=1.524922
nD 20=1.518923
24
nD 20=1.504625
26
起始物料(III)步骤1于0-5℃下,向搅拌的由30g(0.4mol)N-甲基异丙胺、300ml二氯甲烷、120ml水和55g(0.40mol)碳酸钾组成的混合物中徐徐加入45g(0.40mol)氯乙酰氯。20℃下搅拌反应混合物20小时后用水稀释到其体积的两倍并进行摇动。分去有机相、用水洗涤、硫酸钠干燥和过滤后,用真空泵抽真空进行减压蒸馏以小心从滤液中除去溶剂。
得折射率n20 D为1.4700的油状残余物N-甲基-N-异丙基-氯乙酰胺54g(理论值的91%)。步骤2把由52g(0.35mol)N-甲基-N异丙基-氯乙酰胺、10.4g(0.07mol)碳酸钾和0.4ml三乙胺组成的混合物加热到110℃,在此温度下边搅拌边分批加入36g(0.44mol)乙酸钠。然后在120℃下再搅拌此混合物1小时,接着在50-60℃下用200ml甲醇处理。回流4小时后浓缩。残余物同水/二氯甲烷一起摇动。有机相经硫酸镁干燥后过滤。用真空泵抽真空进行减压蒸馏以小心从滤液中除去溶剂。
得折射率n20 D为1.4572的油状残余物N-甲基-N-异丙基-羟基乙酰胺37g(理论值的81%)。
应用实施例实施例A芽前试验溶剂: 5份丙酮(重量计)乳化剂: 1份烷基芳基聚乙二醇醚(重量计)
将1份(重量计)活性化合物与所述量的溶剂混合,加入所述量的乳化剂,浓缩物用水稀释到所希望的浓度以制备适宜的制剂。
把试验植物的种子播在一般土壤中。24小时后用所述活性成分的制剂浇此土壤。适宜的是使单位面积的水量保持恒定。制剂中活性化合物的浓度并不重要,重要的是单位面积上所施用的活性化合物的量。三周后,与对照组植物的的发育情况进行比较,按%损伤率来评定植物的损伤程度。其数值表示:
0%=无效果(如同对照组)100%=全部损伤
在此试验中,试验表明制备实施例2、5、6、8、11、12、13、20、21和24的化合物有很好的杀草作用,而对棉花或大麦这类农作物则有很好的耐受性。
Claims (8)
2.根据权利要求1的化合物(I),其特征在于(I)式中,Het为选自下述基团的任选的苯并稠合和任意取代的杂芳基:噁唑基、异噁唑基、噻唑基、异噻唑基、苯并噁唑基、苯并噻唑基、1,2,4-噁二唑基、1,3,4-噁二唑基、1,2,4-噻二唑基和1,3,4-噻二唑基。所说取代基可优选为下述一组基团中选出的基团:卤素、氰基、(在每一情形下为氟和/或氯任意取代的)C1-C6烷基、C2-C6链烯基、C2-C6炔基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、C1-C6烷基磺酰基-甲基、C3-C6环烷基、苯基、苯氧基甲基、苄磺酰基、吡啶基、呋喃基或噻吩基。
3.根据权利要求1的化合物(I),其特征在于(I)中Het为选自下述基团的任选的苯并稠合和任意取代的杂芳基:1,3-噁唑-2-基、1,3-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,所说取代基可优选为下述一组基团中选出的基团:氟、氯、溴、氰基、(在每一情形下为氟-和/或氯-任意取代的)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、甲基亚硫酰基、乙基亚硫酰基、正-或异丙基亚硫酰基、甲基磺酰基、乙基磺酰基、正-或异-丙基磺酰基、环丙基、环丁基、环戊基、环己基、苯基、吡啶基、呋喃基或噻吩基。
4.一种制备权利要求1的化合物N-甲基-N-异丙基-杂芳氧基乙酰胺(I)的方法,其特征在于下述(II)式取代的杂芳烃与下述N-甲基-N-异丙基-羟基乙酰胺(III)化合物进行反应,如果需要在稀释剂存在下进行并且如果需要,在反应助剂存在下进行,通式(II)中,Het的定义与权利要求1中的定义相同,X为卤素、烷硫基、烷基亚硫酰基或烷基础酰基:
Het-X (II)
5.除草组合物,其特征在于其包含至少一种权利要求1所述的通式(I)化合物。
6.权利要求1所述的通式(I)化合物在防治不需要的植物生长方面的应用。
7.一种除去杂草的方法,其特征在于使权利要求1的化合物(I)对杂草或其环境进行作用。
8.一种制备除草剂组合物的方法,其特征在于使权利要求1的化合物(I)与增量剂和/或表面活性剂混合。
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DE4438178A DE4438178A1 (de) | 1994-10-26 | 1994-10-26 | N-Methyl-N-isopropyl-heteroaryloxyacetamide |
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JP (1) | JPH0912561A (zh) |
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US3557209A (en) * | 1967-10-18 | 1971-01-19 | Velsicol Chemical Corp | Phenoxyacetamides |
US3718455A (en) * | 1970-07-20 | 1973-02-27 | Stauffer Chemical Co | Method of combatting weeds with {60 -naphthoxy acetamides |
DE2961415D1 (en) * | 1978-05-20 | 1982-01-28 | Bayer Ag | Heteroaryloxy-acetamides, process for their preparation and their use as herbicides |
DE3060330D1 (en) * | 1979-04-06 | 1982-06-09 | Bayer Ag | Azolyloxy-acetamides, process for their preparation and their use as herbicides |
DE3148839A1 (de) * | 1981-12-10 | 1983-06-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von hetaryloxyacetamiden |
DE3505425A1 (de) * | 1985-02-16 | 1986-08-21 | Bayer Ag, 5090 Leverkusen | 5-chlor-1,3,4-thiadiazol-2-yloxy-acetamide |
GB8520655D0 (en) * | 1985-08-17 | 1985-09-25 | Fbc Ltd | Herbicides |
DE3821599A1 (de) * | 1988-06-27 | 1989-12-28 | Bayer Ag | Substituierte thiadiazolyloxyessigsaeureamide |
DE3821598A1 (de) * | 1988-06-27 | 1989-12-28 | Bayer Ag | 5-chlor-4-cyano-thiazol-2-yl-oxyessigsaeureamide |
JPH0684363B2 (ja) * | 1989-08-23 | 1994-10-26 | 株式会社トモノアグリカ | 1、2、3―チアジアゾール誘導体、その製造法及び除草剤 |
DE4133827A1 (de) * | 1991-10-12 | 1993-04-15 | Bayer Ag | 2-(2-(fluorphenyl)-1,3,4-thiadiazol-5-yl-oxy)-acetamide |
DE4219246A1 (de) * | 1992-06-12 | 1993-12-16 | Bayer Ag | Neue 2-(7-Chlor-2-benzoxazolyloxy)-acetamide |
DE4223465A1 (de) * | 1992-07-16 | 1994-01-20 | Bayer Ag | Herbizide Mittel auf Basis von Heteroaryloxyacetamiden |
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EP0709380A3 (zh) | 1996-05-08 |
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