CN1015364B - 以卤代乙酰胺化合物作为活性组分的除草剂组合物 - Google Patents

以卤代乙酰胺化合物作为活性组分的除草剂组合物

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CN1015364B
CN1015364B CN86104339A CN86104339A CN1015364B CN 1015364 B CN1015364 B CN 1015364B CN 86104339 A CN86104339 A CN 86104339A CN 86104339 A CN86104339 A CN 86104339A CN 1015364 B CN1015364 B CN 1015364B
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phenyl
compound
alkyl
methyl
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CN86104339A
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CN86104339A (zh
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加藤祥三
竹松哲夫
冈本秀则
小笠原胜
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Tokuyama Corp
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Tokuyama Corp
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Abstract

一种具有以下结构式(I)的卤代乙酰胺化合物：式中：R1为取代或未取代C6-C14芳基或者有选自由O、S、N组成的组中的一个或两个杂原子的取代或未取代的C3-C8杂芳基，R2和R3彼此单独为卤素原子、C1-C6芳基或C1-C6烷氧基或者R2和R3相互连结为C2-C16烷撑基，R4为取代或未取代C1-C12烷基、取代或未取代C6-C14芳基、C2-C12链烯基或C2-C12块基，Y为选自由Cl、Br、I组成的组中的卤素原子，系用作除草剂。

Description

本发明涉及在已有公知文献中所未叙述过的以卤代乙酰胺化合物作为活性组分的除草剂组合物。
更具体地说，本发明涉及一种具有以下结构式（Ⅰ）的卤代乙酰胺化合物：
Figure 86104339_IMG3
……（Ⅰ）
式中：R1代表一种取代的或未取代的C6-C14芳基或者一种取代的或未取代的具有选自由O、S和N组成的组中的一个或二个杂原子的C3-C8杂芳基，
R2和R3彼此单独代表一种氢原子、一种C1-C6烷基或一种C1-C6烷氧基，或者R2和R3连接一起代表一种C2-C16烷撑基，R4代表一种取代的或未取代的C1-C12烷基、一种取代的或未取代的C6-C14芳基、一种C2-C12链烯基或一种C2-C12炔基，Y代表一种选自由Cl、Br和I组成的组中的卤素原子。
本发明还涉及一种制备结构式（Ⅰ）化合物的方法、一种包含结构式（Ⅰ）的化合物作为有效组分的除草组剂以及应用结构式（Ⅰ）的化合物防治不需要植物生长的方法。
众所周知，以下结构式（A）的N-（1-链烯基）-氯代乙酰替苯胺可用作除草剂或者植物生长调节剂（日本公开专利，公告号 947/1983，1983年1月6日公开，相应于西德专利申请P3120990.4）。
Figure 86104339_IMG4
……（A）
在结构式中：
R1代表氢原子或者烷基，
R2代表氢原子或烷基、烷氧基、烷氧基烷基、羟烷基或者苄基，
R3代表氢原子或烷基、链烯基、烷氧基、烷氧基烷基、烷基羰基、烷基羧基烷基、烷氧羰基或者烷氧羰基烷基，如果R1和R2以双键C＝C连接在一起，则代表一种可任意地取代的单个或多个含不饱和键的环，它可以包含杂原子和（或）羰基，或者如果R2和R3以邻近碳原子接连在一起，则可代表一种任意地取代的可以包含杂原子的饱和的或未饱和环，或者R2和R3均代表一种
Figure 86104339_IMG5
结构式的基，其中R6代表氢原了或烷基，R7代表烷基或苯基，
X1、X2和X3彼此单独代表氢或卤素原子或者烷基。
当公知的结构式（A）的氯代乙酰胺化合物在足以获得满意的除草效果的浓度下当作除草剂使用时，会对农作物产生不可忽视的植物毒性。因此，其除草方面的应用是受到限制的。
为了研制一些除草范围广，既能防治稻田杂草又能防治高地杂草，以相当低浓度施药会呈现满意的除草效果以及对作物和植物不产生药害或者对包括人、训养动物和家禽在内的温血动物不产生毒性的除草化合物，本发明人作了广泛地研究。
他们的研究已导致成功地合成公知文献中所未叙述过的结构式（Ⅰ）的化合物，并且导致了揭示这些化合物具有广谱的除草作用，对防治稻田杂草和高地杂草显示了除草活性。本发明人的研究表明，结构式（Ⅰ）化合物以相当低的施药率具有满意的除草效果，而且可以在不对作物和植物以及温血动物产生毒性的情况下控制不需要植物的生长。
本发明人作出的研究结果还发现，为了显示上述的改进的除草活性，关键在于结构式（Ⅰ）中所规定的基本骨架中的R1应当为一种特定的芳基或杂芳基，而与结构式（A）的公知化合物不同。
故而，本发明的一个目的在于提供在已有公知文献中所未叙述过的新的卤代乙酰胺化合物，这些化合物诸如对控制不需要植物的生长是有用的。
本发明的另一个目的在于提供一种制备这些新型的卤代乙酰胺化合物的方法、这些化合物作为除草剂的应用以及用这些化合物控制不需要植物生长的应用方法。
本发明的上述目的和另外一些目的及其优点通过以下叙述将会更明显。
本发明的新型卤代乙酰胺化合物系由以下结构式（Ⅰ）表示。
……（Ⅰ）
在结构式（Ⅰ）中，R1代表取代的或未取代的C6-C14芳基或者取代的或未取代的具有选自由O.S和N组成的组中的一个或二个杂原子的C3-C8杂芳基。
R1所代表的芳基例子是苯基、萘基、蒽基和菲基。优先选用苯基 或者萘基。杂芳基例子是呋喃基、噻嗯基、吡咯基、苯并呋喃基、苯并噻嗯基、吲哚基、噻唑基、吡唑基、咪唑基和吡啶基。优先选用5元环杂芳基和具有稠碳环的5元环杂芳基。
R1所代表的芳基或者杂芳基可以有一个取代基。该取代基包括C1-C6烷基、卤素原子、C1-C6烷氧基、C1-C6卤代烷基、C1-C6硫代烷基、苯氧基、具有一个选自C1-C6烷基和卤素原子（Cl Br、I和F）所取代的苯氧基，苯基以及具有一个选自C1-C6烷基和卤素原子（Cl、Br、I和F）所取代的苯基。
上述的C1-C6烷基取代基的例子是甲基、乙基、正丙基或异丙基、正丁基、异丁基或叔丁基、正戊基和正己基。上述的卤素原子取代基的例子是Cl、Br、I和F。上述的C1-C6烷氧取代基的例子是甲氧基、乙氧基、正或异丙氧基、正、异丁氧基或叔丁氧基、戊氧基和己氧基。可以具有取代的苯氧基或苯基的C1-C6烷基的例子与上述C1-C6烷基取代基所列的相同。
这种取代基取代的以R1代表的芳基的特定例子包括烷基苯基：例如甲苯基、二甲苯基、乙苯基、二乙苯基、丙苯基、二丙苯基、丁苯基、戊苯基、己苯基、甲基乙基苯基;甲基丙基苯基和乙基丙基苯基;卤代苯基：例如氟代苯基、二氟代苯基、氯代苯基、二氯代苯基、溴代苯基、碘代苯基、三氯苯基和氯氟苯基;烷氧基苯基：例如甲氧基苯基、二甲氧基苯基、三甲氧基苯基、乙氧基苯基、二乙氧基苯基、丙氧基苯基和丁氧基苯基;（卤代烷基）苯基：例如（氯代甲基）苯基、（氯代乙基）苯基、（氯代丙基）苯基、（溴代丙基）苯基、（氟代乙基）苯基、（二氟代甲基）苯基、（三氟代甲基）苯基和（二氟溴甲基）苯基;烷基硫代苯基：例如甲基硫代苯基、乙基硫代苯基、丙基硫代苯基和丁基硫代苯基;苯氧基苯基：例如苯氧基苯基、 （甲基苯氧基）苯基、（乙基苯氧基）苯基、（丁基苯氧基）苯基、（氯代苯氧基）苯基、（溴代苯氧基）苯基、（氟代苯氧基）苯基和（氯代甲基苯氧基）苯基;苯基苯基：例如（甲基苯基）苯基、（乙基苯基）苯基、（丙基苯基）苯基、（氯代苯基）苯基、（溴代苯基）苯基、（氟代苯基）苯基和（碘代苯基）苯基;取代的苯基：例如氯代（甲基）苯基、氯代（乙氧基）苯基和甲基（甲氧基）苯基;别的取代的芳基：例如甲基萘基、二甲基萘基、乙基萘基、氯代萘基、溴代萘基、二氯代萘基、甲氧基萘基、（三氟代甲基）萘基、甲基硫代萘基、苯氧基萘基、氯代苯氧基萘基、甲基苯氧基萘基、苯基萘基、氯代苯基萘基、甲基蒽基、乙基蒽基、氯代蒽基、溴代蒽基、甲氧基蒽基、甲基硫代蒽基、苯氧基蒽基、苯基蒽基、甲基菲基、氯代菲基、乙氧基菲基和乙基硫代菲基。
以上述的取代基取代的R1所代表的杂芳基的特定例子包括取代的呋喃基，例如甲基呋喃基、二甲基呋喃基、乙基呋喃基、丙基呋喃基、氯代呋喃基、溴代呋喃基、甲氧基呋喃基、乙氧基呋喃基、丙氧基呋喃基、（三氟代甲基）呋喃基、甲基硫代呋喃基、乙基硫代呋喃基、苯氧基呋喃基、（氯代苯氧基）呋喃基、苯基呋喃基和甲基苯基呋喃基;取代的噻嗯基：例如甲基噻嗯基、乙基噻嗯基、丙基噻嗯基、丁基噻嗯基、氟代噻嗯基、氯代噻嗯基、溴代噻嗯基、碘代噻嗯基、甲氧基噻嗯基、乙氧基噻嗯基、丙氧基噻嗯基、（氯代乙基）噻嗯基、（三氟代甲基）噻嗯基、甲基硫代噻嗯基、乙基硫代噻嗯基、二溴代噻嗯基、二甲氧基噻嗯基、苯氧基噻嗯基、（甲基苯氧基）噻嗯基和氯代苯基噻嗯基;取代的吡咯基：例如N-甲基吡咯基、N-乙基吡咯基、甲基-N-甲基吡咯基、氯代-N-乙基吡咯基、甲氧基-N-甲基吡咯基、（三氟代甲基）-N-甲基-吡咯基、甲基硫代- N-乙基吡咯基、苯氧基-N-甲基-吡咯基和苯基-N-乙基吡咯基;取代的苯并呋喃基：例如甲基苯并呋喃基、氯代苯并呋喃基、乙氧基苯并呋喃基、（三氟代甲基）苯并呋喃基和苯氧基苯并呋喃基;取代的苯并噻嗯基，例如乙基苯并噻嗯基、氟代苯并噻嗯基、甲氧基苯并噻嗯基、甲基硫代基苯并噻嗯基和苯基苯并噻嗯基;甲基噻嗯基;取代的吡唑基：例如二甲基吡唑基和苯基吡唑基;取代的咪唑基，例如甲氧基咪唑基和苯基咪唑基。
在本发明的结构式（Ⅰ）中，R2和R3彼此可单独代表氢原子、C1-C6烷基或C1-C6烷氧基，或者R2和R3连接在一起代表一个C2-C16烷撑基，在此情况下，R2和R3形成具有3-17个碳原子包括它们被结合的碳原子在内的环烯基。
C1-C6烷基包括具有1-6个碳原子的直链或带有支链的烷基，特定的例子是甲基、乙基、正丙基、异丙基、正丁基、异丁基、正戊基和正己基。
C1-C6烷氧基的特定例子是甲氧基、乙氧基、丙氧基、丁氧基、戊氧基和己氧基。
具有2-16个碳原子可由R2和R3连接形成的烷撑基的例子是乙烯基、三甲撑基、四甲撑基、五甲撑基、六甲撑基、七甲撑基、八甲撑基、十甲撑基和十一甲撑基。
本发明的结构式（Ⅰ）的化合物中，R4代表取代的或未取代的C1-C12烷基、取代的或未取代的C6-C14芳基、C2-C12链烯基或C2-C12炔基。
C1-C12烷基包括直链或带支链的烷基，特是例子包括甲基、乙基、正丙基、异丙基、正丁基、异丁基、戊基、己基、庚基、辛烷、壬烷、癸烷、十一烷基十二烷基。
C6-C14芳基的例子包括苯基、萘基、蒽基和菲基。优先选用苯基或者萘基。
C2-C12链烯基的例子包括乙烯基、丙烯基、丁烯基、戊烯基、己烯基、庚烯基、辛烯基、癸烯基、十二烯基。优先选用C2-C6链烯基。
C2-C12炔基的例子包括乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基、辛炔基、癸炔基和十二炔基。优先选用的为C2-C6炔基。
取代基可以取代以R4代表的C1-C12烷基。作为R4烷基取代基的例子包括卤素原子;C1-C6烷氧基;C1-C6硫代烷基;苯氧基;具有选自C1-C6烷基、C1-C6烷氧基、C1-C6硫代烷基和卤素原子中所取代的苯氧基;氰基;苯基;具有选自C1-C6烷基、C1-C6烷氧基、C1-C6硫代烷基和卤素原子中所取代的苯基;具有选自O.S和N中的一个或二个杂原子的C3-C5杂芳基，它可以未取代或由选自C1-C6烷基和卤素原子所取代;具有选自由C1-C6烷基取代或未取代的O.S和N中一个或二个杂原子的C2-C6杂环芳基;在烷氧基部分中具有1-6个碳原子的烷氧基羰基;在可由卤素原子任意地取代的烷基部分具有1-6个碳原子的烷基羰氧基;C2-C6链烯氧基和C2-C6炔基。
关于以R4代表的芳基上的取代基，卤素原子的例子是Cl、Br、I和F，C1-C6烷氧基的例子是甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、正戊氧基和正己氧基。C1-C6硫代烷基的例子是硫代甲基、硫代乙基、正或异硫代丙基、正或异硫代丁基、硫代戊基和硫代己基。作为苯氧基的C1-C6烷基的例子是甲基、乙基、正或异丙基、正或异丁基、戊基和己基。C1-C6烷氧基和C1-C6硫代烷基以及作为苯氧基的取代基的卤素原子的例子可以与上述所给的相同。作为苯基的取代基的例子可以与作为苯氧基的取代基的例子中的上述取代基相同。因此，C1-C6烷基和作为C3-C5杂芳基的取代基的 卤素原子可以是上面给出的相同的烷基和卤素原子。C3-C4杂芳基的例子可以是那些具有作为以R代表的杂芳基例子中的3-5个碳原子的杂芳基。作为以R4代表的烷基的取代基可以有的C2-C6杂环烷基的例子包括四氢呋喃基、四氢噻嗯基、吡咯烷基、四氢吡喃基、四氢硫代吡喃、哌啶基。杂环烷基可以有C1-C6烷基取代基的例子是与上述作为苯氧基的取代基给出的相同的C1-C6烷基。在烷氧基部分中具有1-6个碳原子的烷氧羰基的例子是甲氧羰基、乙氧羰基、丙氧羰基、丁氧羰基和戊氧羰基。具有由一个卤素原子任意取代的C1-C6烷基的烷基羰氧基的例子是甲基羰氧基、乙基羰氧基、丙基羰氧基、丁基羰氧基、戊基羰氧基、（氯代甲基）羰氧基、（溴代乙基）羰氧基、（氟代丙基）羰氧基、（二氯代丙基）羰氧基和（三氟代丁基）羰氧基。C2-C6链烯氧基的例子是乙烯氧基、丙烯氧基、丁烯氧基、戊烯氧基和己烯氧基。C2-C6炔氧基的例子是乙炔氧基、丙炔氧基、丁炔氧基、戊炔氧基和己烯氧基。
本发明的结构式（Ⅰ）的化合物中，以R4代表的C6-C14芳基可以有一个取代基。取代基的例子是卤素原子、未取代或由卤素原子取代的C1-C6烷基、C1-C6硫代烷基和C1-C6烷氧基。卤素原子的例子是Cl、Br、I和F。C1-C6烷基的例子是甲基、乙基、正或异丙基、正或异丁基、戊基和己基。烷基可以有的卤素原子的例子是Cl、Br、I和F。
以R4代表的取代的C1-C12烷基的特定例子包括直链或带支链的卤代烷基，例如氟代甲基、三氟代甲基、氯代甲基、三氯代甲基、氯代乙基、溴代乙基、氟代丙基、氯代丙基、氯代丁基、溴代戊基和氯代己基;直链或带支链的烷氧基烷基：例如甲氧基甲基、甲氧基己基、二甲氧基乙基、甲氧基丙基、甲氧基丁基、甲氧基戊基、甲氧基己基、 乙氧基甲基、乙氧基乙基、二乙氧基乙基、乙氧基丙基、二乙氧基丙基、乙氧基丁基、丙氧基甲基、丙氧基乙基、丙氧基丙基、丙氧基丁基、丁氧基甲基、丁氧基乙基、丁氧基丙基、丁氧基丁基和戊氧基乙基;苯氧基烷基：例如苯氧基甲基、苯氧基乙基、（甲基硫代苯氧基）甲基、（溴代苯氧基）乙基。（氯代苯氧基）乙基、（甲基苯氧基）乙基、（丙氧基苯氧基）乙基和（氯代苯氧基）丙基;氰烷基：例如氰乙基、氰丙基和氰丁基;烷基硫代烷基：例如甲基硫代甲基、甲基硫代乙基、甲基硫代丙基、乙基硫代甲基、乙基硫代乙基、乙基硫代丁基和丙基硫代乙基;苯烷基：例如苯甲基、苯乙基、苯丙基、（乙基硫代苯基）甲基和（氯代苯基）丙基;杂芳烷基：例如噻嗯基甲基、噻嗯基乙基、甲氧基噻嗯基甲基、呋喃基甲基、呋喃基乙基、氯代呋喃基甲基、吡咯基甲基、吡咯基乙基、吡唑基甲基、吡唑基乙基和咪唑基乙基;杂环烷基烷基：例如四氢呋喃基甲基、四氢呋喃基乙基、甲基四氢呋喃基乙基、吡咯烷基乙基、哌啶基乙基、N-甲基吡咯烷基乙基、N-甲基吡咯烷基甲基、甲基哌啶基丙基、四氢噻嗯基甲基和四氢噻嗯基乙基;烷氧基羰基烷基：例如甲氧基羰基甲基、甲氧基羰基乙基、乙氧基羰基甲基、乙氧基羰基乙基、丙氧基羰基乙基、乙氧基羰基丙基和丁氧基羰基丙基;烷基羰氧基烷基：例如甲基羰氧基甲基、甲基羰氧基乙基、甲基羰氧基丙基、乙基羰氧基甲基、乙基羰氧基乙基、乙基羰氧基丙基、丙基羰氧基乙基、（氯代甲基）羰氧基甲基、（氯代甲基）羰氧基乙基、（氯代乙基）羰氧基乙基和（氟代乙基）羰氧基乙基;链烯氧基烷基：例如乙烯氧基甲基、乙烯氧基乙基、丙烯氧基甲基、丙烯氧基乙基、丙烯氧基丙基、丙烯氧基丁基、丁烯氧基乙基和丁烯氧基丙基;炔氧基烷基：例如乙炔氧基甲基、乙炔氧基乙基、丙炔氧基甲基、丙炔氧基乙基、丙炔氧基丙基、丙炔氧 基丁基和丁炔氧基乙基。
在一般结构式（Ⅰ）中，Y为选自氯、溴和碘原子中的卤素原子。Y优先选用的是氯原子或溴原子。
在很多情况下，在结构式（Ⅰ）的化合物中具有上述具体所举的例子中的基团包括各种位的异构体。本发明中可以应用的这种异构体没有任何特别的限制。例如，甲基苯基包括邻甲基苯基、间甲基苯基和对甲基苯基，丁基包括正丁基、仲丁基和叔丁基。
用以下的方法可以确定本发明的一般结构式（Ⅰ）的化合物的结构。
（A）用红外吸收光谱（ir）测定化合物，可以观察到，给予CH键的吸收量大约位在3200-2800厘米-1，给予酰氨基的羰基键的强吸收，大约位在1680-1670厘米-1，给予C＝C键的吸收，大约位在1640-1620厘米-1，有弱吸收。
（B）测定化合物的质谱（ms），并观察相应于各个峰值的组成的分子式。（一般来说，质量数m/e由离子分子量m除以离子电荷数e得到）。这就给出了该化合物的分子量和分子中原子团的结合方式方面的数据。当用以下一般结构式代表化合物时，
Figure 86104339_IMG7
通常，由与在分子中包含的卤素原子数和相应存在的同位素的比率一致的强度比下观察分子离子峰值（缩号为M
Figure 86104339_IMG8
），故而可以确定化合物的分子量。在一般结构式（Ⅰ）的化合物中，可观察到相应于M
Figure 86104339_IMG9
-Y和M
Figure 86104339_IMG10
-COCH2Y的特征峰，进而可知道分子结合的方式。
（C）用1H-核磁共振（1H-nmr）光谱测定，可以确定化合物中 存在的氢原子的结合方式。作为一般结构式（Ⅰ）的化合物的1H-mmr的一个典型的例子（δ.ppm：四甲基硅烷作内部标准，氘代氯仿（CDCl3）作溶剂），图2中所示为N-[1-（苯基）乙烯基]-N-氯乙酰-2′、6′-二甲酰替苯胺;它的1H-nmr图谱经分析结果如下：
Figure 86104339_IMG11
以230ppm观察相应于甲基（d）上6个质子的单谱线;以3.75ppm观察相应于氯乙酰基（c）上2个质子的单谱线;以4.41ppm和4.97ppm观察相应于乙烯基（a）和（b）上1个质子的两个单谱线;以7.10ppm到7.60ppm观察相应于苯环上8个质子的多谱级。
（D）用元素分析确定碳、氢、氮和卤素（当化合物含有硫时还有硫）的重量百分比。以100中减去各个元素确定的总的重量，可以计算出氧的重量百分比。因此，可以确定化合物的组成的分子式。
本发明的各种卤代乙酰胺化合物根据一般结构式（Ⅰ）中的R1、R2、R3、R4和Y的不同以及纯度影响在性质上略有差别。一般来说，在常温和常压下它们是谈黄色到黑褐色的粘性液体或者固体。实施例中将说明特异的性质。本发明的化合物可溶于一般的有机溶剂，例如苯、醚类、醇类、氯仿、乙腈、二甲基甲酰胺和二甲亚砜，但在水中仅少量可溶。
本发明通过选择一般结构式（Ⅰ）中的R1、R2、R3、R4和Y可以提供各种各样新的卤代乙酰胺化合物。以下所示为一般结构式（Ⅰ）的典型化合物的特定实例。
Figure 86104339_IMG13
Figure 86104339_IMG16
Figure 86104339_IMG18
Figure 86104339_IMG19
Figure 86104339_IMG20
Figure 86104339_IMG21
Figure 86104339_IMG22
Figure 86104339_IMG23
Figure 86104339_IMG25
Figure 86104339_IMG26
Figure 86104339_IMG27
用以下的方法可以一般地制备一般结构式（Ⅰ）的化合物，例如：
（ⅰ）一种一般结构式（Ⅰ）的化合物的制备方法，包括使以以下一般结构式表示的席夫碱（Schiff    base）化合物：
Figure 86104339_IMG28
……（Ⅱ）
式中：R1、R2、R3和R4如上规定。
与以一般结构式YCH2COX表示的卤代乙酰卤化物，式中Y代表Cl、Br、或I，X代表Cl、Br、I或F，进行反应。
一般结构式（Ⅲ）的起始席夫碱化合物可以是用任一方法制备的化合物。例如，可以以下反应图通过胺化合物与相应的羰基化合物经脱水缩合而获得。
按要求可以正确地确定上述反应中一般结构式（Ⅱ）的席夫碱化合物和卤代乙酰卤化合物的摩尔比。例如，在相等的摩尔比或稍过量下，应用卤代代酰卤化物。
由于在上述的反应中卤代氢形成副产品，所以优先采用在卤代氢清除剂共同存在时完成该反应。清除剂可以是诸如三乙胺、三丙胺、吡啶、醇钠或者碳酸钠。
在上述的反应中，一般优先采用有机溶剂。该反应中所用的合适的有机溶剂的例子包括苯、甲苯、二甲苯、己烷、石油醚、氯仿、二氯甲烷、乙醚、二恶烷、四氢呋喃、丙酮、甲基乙基酮、乙腈、N，N-二甲基甲酰胺、六甲基磷酰胺和二甲亚砜。
然而在很多情况下优先采用碱性极性溶剂，例如N，N-二甲基甲酰胺、N，N-二甲基乙酰胺或者六甲基磷酰胺作为反应的溶剂，在没有清除副产品卤化氢用的清除剂存在的情况下，在这样的溶剂中反应易于进行，而且最后的卤代2酰胺化合物能得到高的收率。
加入起始原料的次序并无特别限制，例如式Ⅰ的席夫碱化合物溶解在一种溶媒中而继后将卤代2酰卤化合物在搅拌下加至溶液中。
反应温度可以一个宽的范围内选择，例如-20到150℃，优先选择-10到120℃。反应时间随起始物料的类型和反应温度不同而不同。例如，5分钟到10天，优先选择1小时到50小时。反应最好在搅拌下进行。
对从反应后混合物中分离一般结构式（Ⅰ）的最终化合物和纯化它的方法并没有特别限制，可以采用任一公知的方法。例如，可用馏出反应溶剂和反应之后的卤化氢清除剂，将水加入到残留物中，用诸如苯、醚或氯仿等有机萃取溶剂萃取混合物，用诸如硫酸钠或者氯化钙干燥剂干燥有机层，馏出溶剂以及真空蒸馏残留物。还可以用层析法、重结晶等方法进行纯化。
应用诸如N，N-二甲基甲酰胺酰胺类型极性溶剂作为反应溶剂往往可排除对卤化氢清除剂的需要。在反应之后，馏出低沸点物质，然后残留物仅经真空蒸馏，可以获得最终的化合物。另一种方法，在反应之后，将水加入到反应混合物中，用诸如苯、醚或者氯仿有机萃取溶剂萃取混合物。用诸如醇酸钠干燥剂干燥有机层。馏出溶剂，用真空蒸馏层析法或者重结晶使残馏物纯化。获得最终的化合物。
（ⅱ）一般结构式（Ⅰ）的卤代乙酰胺还可以用一种方法制备，这种方法包括使由以下一般结构式表示的席夫碱化合物。
……（Ⅲ）
式中：R1、R2和R3如上所规定，R8和R9是相同的或者不同的，每个代表一种氢原子或者是与R4相同，除了碳原了的最大数比R4的最大碳原子数少1个之外，与一般结构式YCH2COX的卤代乙酰卤化物进行反应，式中Y和X如上所规定，在存在或者无硅烷情况下，硅烷由以下结构式表示：
式中：X4、X5和X6是相同的或者是不同的，每个代表一个氢原子或者一个卤素原子。
在上述反应中，反应温度例如为20到150℃，反应时间是5分钟到10天。按照需要，反应可以在与反应（ⅰ）所述的相同溶剂中进行，例如苯、甲苯、乙腈和氯仿。
当在无硅烷化合物下应用上述的反应时，最好使反应在反应系统中有公知的卤化氢清除剂的情况下进行。
（ⅲ）一般结构式（Ⅰ）的卤代乙酰胺化合物还可用另一种方法制备，这种方法包括使上述的一般结构式（Ⅲ）的席夫碱化合物与由一般结构式YCH2COX表示的卤代乙酰卤化物反应，式中Y和X如上所规定，尔后使产物与以下结构式表示的化合物反应。
A-R10
式中：A代表一个氢原子、锂原子、钠原子、钾原子、锌原子或具有1-4个碳原子的（三烷基）甲硅烷基，R10与作为R4的取代的烷基中的取代基相同。
在该反应中最好应用有机溶剂。有机溶剂的例子是苯、甲苯、己烷、二氯甲烷、氯仿、乙腈、乙醚、N，N-二甲基酰胺和二甲亚砜。上述结构式A-R10中A处是一个氢原子，最好应用公知的卤化氢清除剂，例如三乙胺、吡啶、碳酸钠和碳酸钾。在上述的反应中，最好的反应温度，例如-20到150℃，最好的反应期，例如5分钟到10天。
本发明提供的一般结构式（Ⅰ）的化合物作为除草剂具有极好的效果，例如在禾本科的杂草、阔叶的杂草和多年生的杂草的幼苗出土前、后的土壤处理。具体地说，当用作高地除草剂时，它们具有选择性的除草效果。因此不仅可施药于阔叶的作物，例如大豆、棉花和甜菜，而且可施药于禾木科的作物，例如小麦、大麦、玉米和早稻。它们对草地也具有有极好的选择性的除草活性。具有特异骨架的一般结构式（Ⅰ）的化合物还有良好的防治水稻杂草的选择除草效果。
通过合适地选择一般结构式（Ⅰ）中的R1、R2、R3、R4和Y，本发明的化合物作为除草剂用于高地、草地和水稻田具有极好的除草效果。可以用本发明的化合物施药且有特别良好的效果的杂草的例子包括高地田杂草和草地杂草，例如大马唐草（large crabgrass）（Digitaria ciliaris Koeler）、猪殃殃（goosegrass）（Eleusine indica）、绿狐尾草（green foxtail）（Setaria viridis Beauvois）、普通藜（common lamb′s quarters）（Chenopodium album L.）、刺草（smartweed）（Polygonum longisetum De.Bruyn.）、大刺草（large smartweed）[poiygonum lapathifolium L.subsp.nodosum（Pers.）Kitam]、黄色的坚果芦苇（yellow nutsedge）（Cyperus microiria Steud.）、黄莎草（yellow cyperus）（Cyperus iria L.）、猪草（pigweed）（Amaranthus lividus L.）、普通马齿苋（common purslane）（Portulaca oleracea L.）、红荷兰翘 摇（red    clover）（Trfifoliun    pratense    L.）、匍匐酢浆草（creeping    woodsorrel）（Oxalis    corniculata    L.）、水狐尾草（water    foxtail）（Alopecurus    aequalis    Sorol.）、早熟禾（annual    bluegrass）（Poa    annua    L，）、蓬子菜（bedstraw）（Galium    spurium    L.）、野牵牛（blue    morning    glory）（Ipomoea    indica    Merrill）、“决明子属”“kawaraketsumei”）（Cassia    nomame    Honda）、普通大巢菜（common    vetch）（Vicia    sativa    L.）、荠菜（shepherd′spurse）（Capsella    bursa-pastoris    Medik.）和三叶鬼针草（hairy    beggartics）（Bidens    pilosa）;水稻杂草，例如稗草（barnyard    grass）[Echinochloa    crus-galli    Beauv.;Echinochloa    oryzicola    Vasing）、伞形植物（umbrella    plant）（Cyperus    difformis    L.）牧原水沙草（three-square    grass）（Scirpus    juncoides    Rxb.）、“美图八钓”（“mizugayatsuri”）（Cyperusserotinus    Rottr.）、“水蜈蚣属沙草”（“himekugu”）（Kyllin-ga    brevifolia    Rottr.）、欧菱（water    chustnut）（Eleocharis    kuroguwai    Ohwi）、牛毛毡（slender    spikerush）（Eleocharis    acicularis，Roem.et    Schult.）、河藨草（river    bulrush）（Scirpus    planiculmis    Fr.Schm.）三叶慈姑（arrowhead）（Saqittaria    trifolia    L.）、“阿木梨”慈姑（“aginshi”）（Saqittaria    aqinashi    Makino）、窄叶泽泻（narrowleaf    water-plantain）（Alisma    canaliculatum，A.Bn，et    Couche）、绿叶慈姑（“urikawwa”）（Saqittaria    pygmaea    m    iq.）、大叶眼子菜（largeleaf    pondweed）（Potamogeton    distinctus    A.Benn.）、六瓣合叶子（dropwort）（Oenanthe    iavanica    de    Candolle）、鸭舌草（monochoria）（Monochoria    vaginalis    Presl.）、水竹叶 （“ibokusa”）（Aneilema    Keisak    Hand-Mazt.）、沟繁缕（water    wort）（Elatine    triandra    Schk.）多叶水苋菜（“him-emisohagi”）（Ammannia    multiflora    Roxb.）丁香蓼（false    loo-sestrife）（Ludwigia    prostrata    Roxb.）、半边莲（“azemushiro”）（Lobelia    chinensis    Lour）、狼地草（burmarigold）（Bidens    tripartita    L.）、黑魔鬼针草（devil′s    beggarticks）（Bidens    frondosa    L.）、“阿武纳米”（“abunome”）（Dopatrium    junceum    Hamilt.）、母草（false    pimpernel）（Lindernia    pyxidaria    L.）和玄参（“azetogarashi”）（Vandellia    angus-tifolia    Bentham）。
具有特别好的除草效果且可易于在工业上制备的一般结构式（Ⅰ）的卤代乙酰胺化合物，例如是一些一般结构式（Ⅰ）中R1是未取代的苯基或者由C1-C6烷基、C1-C6烷氧基或苯氧基取代的苯基;R2和R3每个代表一个氢原子或C1-C4烷基;R4是C1-C6烷基、C1-C6烷氧基烷基或由C1-C4烷基和（或）C1-C4烷氧基所取代的苯基。上述化合物的典型例子包括以下的。
Figure 86104339_IMG32
Figure 86104339_IMG33
一般结构式（Ⅰ）的化合物作为除草剂在以一般2到3000克/10公亩的施药量，优先采用10到1000克/10公亩，更好采用30到600克/10公亩，应用时，具有足够的除草效果。
一般结构式（Ⅰ）的化合物往往可方便地与公知的除草剂掺和使用，例如苯氧基类型化合物、三氮嗪类型化合物、酰胺类型化合物、吡唑酯类型化合物、磺酰脲类型化合物等等，因为混合使用能减少各个化合物的数量而且预计产生协同效应。
因为一般结构式（Ⅰ）的化合物对植物生长有影响，所以它们还可用脱叶剂，发芽抑制剂和生长调节剂。
应用一般结构式（Ⅰ）的化合物的方法可以是公知除草剂所应用的方法。例如，它们可以做成合适的形式，比如颗粒剂、粉尘剂、乳油、可湿性粉剂、片剂、油剂、气雾剂或者由用农业可接受的固体或液体稀释剂或载体做成的熏蒸剂。按照需要，还可以掺入农业上可接受的辅助剂，例如粘着剂、稀释剂、表面活性剂，分散剂和溶剂使用。 这种除草组剂可包含除草有效量，例如，一般结构式（Ⅰ）的化合物的大约0.1%到大约90%。
本发明的一般结构式（Ⅰ）的化合物还可以与杀虫剂、杀菌剂、其他农药、肥料、土壤调节剂等等掺和使用。
这样，本发明所提供的除草组成包括以一般结构式（Ⅰ）表示的卤代乙酰胺化合物的除草有效量和农业上可接受的稀释剂或者载体。
本发明另外还提供一种控制不需要植物的生长的方法，该方法包括把一般结构式（Ⅰ）的卤代乙酰胺化合物的有效量施散到不需要植物的场合。
以下的实施例将对本发明作更具体地说明。应当认为，本发明并不仅仅限于这些实施例。
实施例1
将N-（1-甲基苄叉基）-2′，6′-二甲基替苯胺（4.57克、0.020摩尔）溶入25毫升N，N-二甲基甲酰胺（缩写为DMF）中。在室温下搅拌，逐渐地加入5毫升DM.F中有2.48克（0.022摩尔）的氯乙酰氯的溶液。混合物在室温下搅拌一会儿，然后在60℃下加热2小时。将反应溶液冷却到室温，用100毫升醚洗涤两次。再用100毫升醚萃取有机层。醚层用硫酸钠干燥，然后将醚馏出，所得固体用苯和己烷的混合物中重结晶出最终的固体，获得4.34克无色晶体，其熔点为91-92℃。
测定无色晶体的红外吸收光谱，并示于图1中。红外吸收光谱图说明了给予C-H键的吸收系在3100-2900厘米-1，给予酰胺基的羰基键的强吸收，系在1680厘米-1，给予＞c＝c＜键的弱吸收，系在1615厘米-1。
产物的质谱说明分子离子峰（M
Figure 86104339_IMG34
）在m/e 299，相应于M
Figure 86104339_IMG35
-Cl的峰在m/e264，相当于M
Figure 86104339_IMG36
-COCH2Cl的峰在m/e222。
测定产物的1H-核磁共振光谱（δ，ppm：四甲基硅烷作内部标准，氘代氯仿作溶剂）其结果示于图2。其分析结果如下：
苯环    …7.10-7.60    ppm    （8H）
产物的元素分析表明，C72.08%、H5.98%、N4.80%;与以组成分子式C18H18NClO（299.80）的计算值，C72.11%、H6.05%、N4.67%，基本上一致。
上述结果可以确定，分离出的产物是N-（1-苯）乙烯基-N-氯乙酰-2′，6′-二甲基替苯胺。其收得率为71%。这种化合物标以1号化合物。
实施例2
将N-（乙氧基甲叉）-（1-苯基-2，2-二甲基乙烯基）胺（1.12克，0.0055摩尔）溶入15毫升苯中，以搅拌冷却，并一滴滴地逐渐加入在5毫升苯中有0.80克（0.0071摩尔）氯乙酰氯和1.02克（0.0075摩尔）三氯硅烷的溶液。混合物在室温下搅拌过夜，再在冰冷却下用碳酸钾水溶液中和。用醚苯取有机层，用硫酸钠干燥。使低沸点组分蒸发，用柱层析法（硅胶）纯化最终黄色液体，获得0.71克淡黄色粘性液体。
最终化合物的红外吸收光谱表明，给予C-H键的吸收系在 3100-2800厘米-1，给予酰胺的＞C＝O键是强吸收，系在1680厘米-1，给予＞C＝C＜键的吸收系在1600厘米-1。
产物的质谱表明，分子离子峰（M ）在m/e281，相应于M
Figure 86104339_IMG39
-OC2H5的峰在m/e236，相应于M
Figure 86104339_IMG40
-CH2OC2H5的峰在m/e222。
测定产物的1H-核磁共振谱（δ，ppm：四甲基硅烷作为内部标准，氘代氯仿作溶剂）。
其分析得结果如下：
Figure 86104339_IMG41
（a）7.20ppm    （s，5H）
（b）1.86ppm    （s，6H）
（c）4.10ppm    （s，2H）
（d）5.01ppm，4.48ppm（d，d，2H）
（e）3.60ppm    （q，2H）
（f）1.12ppm    （t，3H）
产物的元素分析值为C64.10%、H7.09%、N5.01%，与以组成分子式C15H20NClO（281.78）的计算值，C63.94%、H7.15%、N4.97%基本上一致。
由上述结果可以确定，分离出的产物是N-（1-苯基-2，2-二甲基）乙烯基-N-氯乙酰-乙氧基甲酰胺。收得率为46%。最终化合物标以2号化合物。
实施例3
将N-（1-苯基-2，2-甲基）乙叉基-2′-甲氧基乙胺（2.06克，0.01摩尔）溶入20毫升DMF中，在室温下搅拌，逐渐地加入1.52克（0.013摩尔）氯乙酰氯。溶液在60℃下加热2小时，然后冷却到室温，用水和碳酸钠溶液洗涤。用醚萃取有机层，醚层用硫酸钠干燥，再馏出醚。用柱层析法（硅胶）纯化最终的粘性液体，获得1.90克淡黄色粘性液体。
最终化合物的红外吸收光谱表明，给予C-H键的吸收系在3100-2800厘米-1，给予酰胺的＞C＝O键以强吸收系在1670厘米-1，给予＞C＝C＜键的吸收系在1600厘米-1。
最终化合物的质谱表明，分子离子峰（M
Figure 86104339_IMG42
）在m/e281，相应于M
Figure 86104339_IMG43
-OCH3的峰在m/e266，相应于M -Cl的峰m/e246。测定最终化合物的1H-核磁共振光谱（δ，ppm：四甲基硅烷作内部标准，氘化氯仿作溶剂）。分析结果如下所示。
Figure 86104339_IMG45
产物元素分析值为C63.83%、H7.21%、N5.12%，与以组成分子式C15H20NCl    O（281.78）的计算值C63.94%、H7.15%、N4.97%基本上一致。
由上述结果可以确定，分离出的产物是N-[1-（苯基）-2，2-（二甲基）-乙烯基]-N-氯乙酰-2′-甲氧基乙酰胺。产物的收得率为67%。最终化合物标以3号化合物。
实施例4
在搅拌冷却下，将5毫升苯中有1.12克（0.0099摩尔）氯乙酰氯的溶液逐渐地一滴滴地加入到10毫升苯中有1.29克（0.0074摩尔）N-乙烯基-（1-苯基-2，2-二甲基-乙烯基）胺的溶液中。混合物在冰冷却下搅拌30分钟，然后一滴滴地加入1.41克（0.010摩尔）N-三甲硅烷基吡唑。在室温将混合物搅拌过夜。用水洗涤反应混合物，用苯萃取有机层。有机层用硫酸钠干燥，再去除低沸点组分。所得黄色粘性液体用柱层析法（硅胶）纯化最终获得1.00克无色晶体。
最终化合物的红外吸收光谱表明，给予C-H键的吸收系在3200-2800厘米-1，给予酰胺的＞c＝o键以强吸收，系在1665厘米-1。
产物的质谱表明，分子离子的峰（M
Figure 86104339_IMG46
）在m/e318，相应于
Figure 86104339_IMG47
的峰在222，相应于
Figure 86104339_IMG48
的峰在m/e95。
测定1H-核磁共振光谱（δ，ppm：四甲基硅烷作内部标准，氘代氯仿作溶剂）。其分析结果如下所示。
（a）7.29ppm（s，5H）
（b）1.47ppm（d，6H）
（c）4.38ppm，4.00ppm（dd，2H）
（d）1.27ppm（d，3H）
（e）6.93ppm（q，1H）
（f）7.60ppm（d，1H）
（g）6.19ppm（m，1H）
（h）7.42ppm（d，1H）
产物元素分析值为C64.41%、H6.29%、N12.98%，与以组成分子式C17H20NCl    O（317.81）的计算值C64.24%、H6.34%、N13.22%基本上一致。
由上述结果可以确定，分离出的产物是N-[1-（苯基）-2，2-（二甲基）-乙烯基]-N-氯乙酰-[1′-（1″-吡唑基）乙基]酰胺。收得率为42%。最终化合物标以4号化合物。
实施例5
按照实施例1到4合成各种氯代乙酰胺化合物。表1汇总了所合成的化合物的外观、沸点或者熔点、红外吸收光谱中的特征吸收以及元素分析值。表中R1、R2、R3和R4与以下结构式中的R1、R2、R3和R4相应。
表1中的沸点在减压下（mm    Hg）测定，并且省略了mmHg，例如153℃/0.9（＝153℃/0.9mm    Hg）。
Figure 86104339_IMG52
Figure 86104339_IMG53
Figure 86104339_IMG54
Figure 86104339_IMG55
Figure 86104339_IMG56
Figure 86104339_IMG57
Figure 86104339_IMG58
Figure 86104339_IMG59
实施例6
按照实施例1到5合成各种囟代乙酰胺化合物。这些化合物的结构由红外吸收光谱、质谱分析、1H-核磁共振光谱分析以及元素分柝确定。表2汇总了这些化合物的取代基和元素分析值。表中R1、R2、R3和R4和Y与以下结构式中的R1、R2、R3和R4相应。
Figure 86104339_IMG60
Figure 86104339_IMG61
Figure 86104339_IMG62
Figure 86104339_IMG63
Figure 86104339_IMG64
Figure 86104339_IMG65
Figure 86104339_IMG66
Figure 86104339_IMG67
Figure 86104339_IMG68
Figure 86104339_IMG69
Figure 86104339_IMG70
Figure 86104339_IMG71
Figure 86104339_IMG73
Figure 86104339_IMG74
Figure 86104339_IMG75
Figure 86104339_IMG76
Figure 86104339_IMG78
Figure 86104339_IMG81
Figure 86104339_IMG83
Figure 86104339_IMG84
配方实施例1
可湿性粉剂：
将10份在实施例1中所得的N-（1-苯基）乙烯基-N-氯乙酰-2′，6′-甲酰替苯胺（1号化合物）、85份Zieklite（商品名，Zieklite    Kogyo    K、K的产品）和Kunilite（商品名，Kogyo    Kunimine    K.K的产品）2∶1的混合物以及5份作为表面活性剂的Sorpol    800    A（商品名，Toho    Chemical    Industrial    Co.，Ltd.的产品）混合，并均匀地制成粉状，获得10%可湿性粉剂。
配方实施例2
乳剂：
将20份在实施例2中所得的N-（1-苯基）-2，2-二甲基-乙烯基-N-氯乙酰-乙氯基甲酰胺（2号化合物）、70份二甲苯以及10份作为表面活性剂的Sorpol    8ooA混合成20%乳剂。
配方实施例3
颗粒剂：
将5份N-（1-苯基-2，2-二甲基）乙烯基-N-氯乙酰-2′-甲氧基乙酰胺（3号化合物）、50份膨润土（bentonite）（商品名，Kunimine    K.K产品）、40份Kunilite以及5份作为表面活性剂的Sorpol    800A混合并均匀地制成粉状。加水，再均匀地搅拌，形成一种膏状混合物。使混合物从直径0.7毫米的孔中挤出，干燥，按1到2毫米的长度切断，即形成5%颗粒剂。
实施例7
将高地田土壤（沃土）装填在瓷盆中（1/8850公亩）。在深为0.5到1厘米的土壤中播种各种植物的种子。将按配制实施例1制备的表1中所示的每种化合物的可湿性粉剂的水稀释液以预定的施药数量喷洒在土壤的表面上。处理后，在平均气温保持在25℃的暖房中使 植物生长。两周之后，检验每种试验化合物的除草效果，其结果示于表3。
以6个等级来作评价，其中0级表示正常生长，5级表示完全杀死，而1到4级表示“正常生长”和“完全杀死”之间的不同生长程度。
在表3中的化合物序号栏中A是一种作对照比较用的有以下结构式的公知囟代乙酰苯胺。
A化合物
表3中所列的结果说明，本发明的结构式（Ⅰ）的化合物与A化合物相比具有更好的除草府活性和除草选择性。
表3
化合物    施药量    植物
（克/10    a    b    c    d    e    f    g    h    i    j    k    l    m
序号    （公亩）
1    600    0    0    0    0    0    5    5    5    5    4    3    5    4
300    0    0    0    0    0    5    5    5    4    4    2    4    3
2    600    0    0    0    0    0    5    5    5    5    5    5    5    5
300    0    0    0    0    0    5    5    5    5    5    4    5    5
3    600    0    0    0    0    0    5    5    5    5    5    4    5    5
300    0    0    0    0    0    5    5    5    5    5    4    5    5
4    600    0    0    0    0    0    5    5    5    3    3    3    4    3
300    0    0    0    0    0    5    5    5    3    3    3    3    3
7    600    0    0    0    0    0    5    5    5    4    3    1    3    3
300    0    0    0    0    0    4    4    3    3    2    0    1    0
14    600    0    0    0    0    0    5    5    5    5    5    4    5    5
300    0    0    0    0    0    5    5    5    5    5    3    5    5
18    600    0    0    0    0    0    5    5    5    5    5    4    5    5
300    0    0    0    0    0    5    5    5    5    5    4    5    5
21    600    0    0    0    0    0    5    5    5    3    4    2    4    3
300    0    0    0    0    0    5    5    5    3    2    1    3    0
29    600    0    0    0    0    0    5    5    5    5    5    4    5    5
300    0    0    0    0    0    5    5    5    5    5    4    5    5
32    600    0    0    0    0    0    5    5    5    5    4    3    4    4
300    0    0    0    0    0    5    5    5    5    4    2    4    2
33    600    0    0    0    0    0    5    5    5    5    5    4    5    5
300    0    0    0    0    0    5    5    5    5    5    4    5    4
34    600    0    0    0    0    0    5    5    5    5    4    3    4    4
300    0    0    0    0    0    5    5    5    5    4    2    3    4
35    600    0    0    0    0    0    5    5    5    5    5    5    5    5
300    0    0    0    0    0    5    5    4    5    5    4    5    4
续下
表3    续上
36    600    0    0    0    0    0    5    5    5    5    4    4    4    4
300    0    0    0    0    0    5    5    5    4    3    3    3    3
37    600    0    0    0    0    0    5    5    5    5    5    4    5    5
300    0    0    0    0    0    5    5    5    4    4    4    5    5
38    600    0    0    0    0    0    5    5    5    5    4    5    5    5
300    0    0    0    0    0    5    5    5    4    4    3    3    4
39    600    0    0    0    0    0    5    5    5    5    5    5    5    5
300    0    0    0    0    0    5    5    5    5    5    4    5    5
40    600    0    0    0    0    0    5    5    5    5    5    4    5    5
300    0    0    0    0    0    5    5    5    5    4    3    4    4
42    600    0    0    0    0    0    5    5    5    4    5    4    4    4
300    0    0    0    0    0    4    4    5    4    3    2    4    3
44    600    0    0    0    0    0    5    5    5    5    5    4    5    5
300    0    0    0    0    0    5    5    5    3    5    4    5    5
45    600    0    0    0    0    0    5    5    5    5    5    5    5    5
300    0    0    0    0    0    5    5    5    4    4    4    5    5
46    600    0    0    0    0    0    5    5    5    4    4    1    3    3
300    0    0    0    0    0    5    5    4    4    2    0    2    1
49    600    0    0    0    0    0    5    5    5    5    5    5    5    5
300    0    0    0    0    0    5    5    5    5    4    4    4    4
112    600    0    0    0    0    0    5    5    5    5    5    5    5    5
300    0    0    0    0    0    5    5    5    4    4    4    4    4
122    600    0    0    0    0    5    5    5    5    5    4    5    5
300    0    0    0    0    5    5    5    4    3    4    3    4
123    600    0    0    0    0    0    5    5    5    4    5    4    5    5
300    0    0    0    0    0    5    5    4    4    4    4    4    4
132    600    0    0    0    0    0    5    5    5    5    5    5    5    5
300    0    0    0    0    0    5    5    5    3    4    3    3    3
续下
表3    续上
139    600    0    0    0    0    0    5    5    5    5    5    4    5    5
300    0    0    0    0    0    5    5    5    5    4    4    4    4
146    600    0    0    0    0    0    5    5    5    5    5    5    5    5
300    0    0    0    0    0    5    5    5    4    4    3    4    4
147    600    0    0    0    0    0    5    5    5    5    5    4    5    5
300    0    0    0    0    0    5    5    5    5    5    3    4    4
152    600    0    0    0    0    0    5    5    5    5    4    4    5    5
300    0    0    0    0    0    5    5    5    4    4    3    4    4
165    600    0    0    0    0    0    5    5    5    4    4    4    4    4
300    0    0    0    0    0    4    4    4    4    3    4    3    4
191    600    0    0    0    0    0    5    5    5    5    5    4    5    5
300    0    0    0    0    0    5    5    5    5    4    4    4    4
248    600    0    0    0    0    0    5    5    5    4    4    5    5    4
300    0    0    0    0    0    4    4    4    3    4    4    3    4
262    600    0    0    0    0    0    5    5    5    5    5    5    5    5
300    0    0    0    0    0    5    5    4    4    4    4    4    4
265    600    0    0    0    0    0    5    5    5    5    5    4    4    4
300    0    0    0    0    0    4    4    4    4    3    4    4    4
A    600    4    2    2    2    2    5    5    4    4    4    3    4    3
300    3    1    1    1    1    4    4    3    2    2    3    3    2
在表3中，“植物”栏中的字母a到m代表以下植物。
a：稻子
b：小麦
c：玉米
d：大豆
e：棉花
f：稗子
g：马唐草
h：绿狐尾草
i    藜
j    大蓼车草
k：野牵牛
l：黄沙草
m：毛鬼针草
实施例8
以与实施例7中的相同方法，以较低的施药量，把表4中所示的每种试验化合物作土壤处理试验，其结果示于表4。
表4中化合物序号栏中所列的A、B和C代表以下化合物。
A化合物（与实施例7中相同）
B化合物的结构式如下：
Figure 86104339_IMG86
C化合物的结构式如下：
Figure 86104339_IMG87
从表4中所列的结果可以明显地看出，本发明的活性化合物与作比较用的化合物A、B和C相比具有更好的除草活性。表4中“植物”栏中所列的字母a到m与表3中意思相同。
表4
化合物    施药量    植物
（克/10    a    b    c    d    e    f    g    h    i    j    k    l    m
序号    公亩）
2    50    0    0    0    0    0    5    5    5    5    4    3    4    4
3    50    0    0    0    0    0    5    5    5    5    4    3    3    4
18    50    0    0    0    0    0    4    4    4    3    2    2    2    2
32    50    0    0    0    0    0    5    5    5    3    3    3    2    2
35    50    0    0    0    0    0    5    5    5    5    4    3    4    3
39    50    0    0    0    0    0    5    5    5    5    5    3    4    4
45    50    0    0    0    0    0    5    4    5    3    3    2    2    2
49    50    0    0    0    0    0    5    5    5    4    3    3    3    3
112    50    0    0    0    0    0    4    4    5    3    3    2    2    2
132    50    0    0    0    0    0    5    5    5    4    3    2    2    2
139    50    0    0    0    0    0    4    4    4    3    3    3    4    3
262    50    0    0    0    0    0    5    5    5    3    3    3    3    3
A    50    2    0    0    0    0    2    2    2    1    1    1    0    0
B    50    1    0    0    0    0    2    1    1    1    0    0    0    0
C    50    2    0    0    0    0    2    0    0    1    0    0    0    0
实施例9
将高地田土壤（沃土）装填在瓷盆中（1/8850公亩），在深度为0.5到1厘米的土壤中播种不同植物的种子，在平均气温保持在25℃的暖房中生长。两周之后，将按配制实施例1制备的表5中所示的每种试验化合物的可湿性粉剂的水的稀释液以预定的施药量喷洒在植物的枝叶上。处理之后，植物在暖房中生长，两周之后，检验每种试验化合物的除草效果，以与实施7中的标准评定。其结果示于表5。
表5中代表植物的字母与表3的相同。
表5
化合物    施药量    植物
（克/10    a    b    c    f    g    h    d    e    i    j
序号    公亩）
1    800    0    0    0    5    5    5    0    0    0    0
400    0    0    0    5    4    5    0    0    0    0
2    800    0    0    0    5    5    5    0    0    2    1
400    0    0    0    5    5    5    0    0    2    1
3    800    0    0    0    5    5    5    0    0    2    1
400    0    0    0    5    5    5    0    0    1    1
4    800    0    0    0    5    4    5    0    0    0    0
400    0    0    0    5    4    4    0    0    0    0
18    800    0    0    0    5    5    5    0    0    1    0
400    0    0    0    5    4    5    0    0    0    0
29    800    0    0    0    5    5    5    0    0    1    0
400    0    0    0    5    5    5    0    0    0    0
33    800    0    0    0    5    5    5    0    0    2    0
400    0    0    0    5    4    4    0    0    0    0
35    800    0    0    0    5    5    5    0    0    2    2
400    0    0    0    5    5    5    0    0    1    0
39    800    0    0    0    5    5    5    0    0    2    2
400    0    0    0    5    5    5    0    0    2    1
44    800    0    0    0    5    5    5    0    0    0    0
400    0    0    0    5    4    4    0    0    0    0
46    800    0    0    0    5    5    5    0    0    1    1
400    0    0    0    5    4    5    0    0    0    0
实施例10
将加水拌和的水稻田土壤（淤积土）装填在瓷盆中（1/8850公亩）。播种水稻杂草种子并将3叶期稻秧（品种：“akinishiki”）插植深1厘米。加水保持浸没深度3厘米。将接配方实施例1制备的表6中所示的每种试验化合物的可湿性粉剂的水稀释液以预定的施药量滴入杂草发芽时的模似水稻中。在平均气温保持在25℃的暖房中使植物生长。三周之后，检验化合物的除草效果并按与实施例7中相同的标准评定。其结果示于表6。在表6中，字母f与表3中的相同，字母n到q代表以下植物。
n：伞莎草（umbrella    plant）
o：牧原水沙草（three-squre    grass）
p：雨久花属（monochoria）
q：车前草[false    pimpernel，“azetogarashi”
（Vandellia    angustifolia    Bentham）和
“kikashigusa”（Rotala    Indica    Koehne）]
表6
化合物    施药量    除草效果    移植的稻子
（克/10    f    n    o    p    q
序号    公亩）
1    500    5    5    5    5    5    0
250    5    5    5    5    5    0
2    500    5    5    5    5    5    0
250    5    5    5    5    5    0
3    500    5    5    5    5    5    0
250    5    5    5    5    5    0
4    500    5    5    5    5    5    0
250    5    5    5    5    5    0
5    500    5    4    4    4    4    0
250    4    3    3    4    3    0
6    500    5    5    5    5    5    0
250    5    5    5    5    5    0
7    500    5    5    5    5    5    0
250    5    5    5    5    5    0
8    500    5    5    5    5    5    0
250    5    5    5    5    5    0
9    500    5    5    5    5    5    0
250    4    3    3    3    3    0
10    500    5    5    5    5    5    0
250    5    5    5    5    5    0
11    500    5    5    5    5    5    0
250    5    5    4    5    4    0
12    500    5    5    5    5    5    0
250    5    5    5    5    5    0
13    500    5    5    5    5    5    0
250    5    5    5    5    5    0
续下
表6    续上
14    500    5    5    5    5    5    0
250    5    5    5    5    5    0
15    500    5    5    5    5    5    0
250    5    5    5    5    5    0
16    500    5    5    5    5    5    0
250    5    5    4    5    4    0
17    500    5    5    5    5    5    0
250    5    5    5    5    4    0
18    500    5    5    5    5    5    0
250    5    5    5    5    5    0
19    500    5    5    3    3    3    0
250    4    4    3    3    3    0
20    500    5    5    5    5    5    0
250    5    5    5    5    5    0
21    500    5    5    5    5    5    0
250    4    4    4    2    4    0
22    500    5    5    5    5    5    0
250    5    5    5    5    5    0
23    500    5    5    5    5    5    0
250    5    4    4    4    4    0
24    500    4    3    5    5    4    0
250    3    3    4    0    2    0
25    500    5    5    5    5    5    0
250    5    5    5    5    5    0
26    500    5    5    5    5    5    0
250    5    5    5    5    5    0
27    500    5    5    5    5    5    0
250    4    4    4    4    4    0
续下
表6    续上
28    500    5    5    5    5    5    0
250    5    4    4    4    3    0
29    500    5    5    5    5    5    0
250    5    5    5    5    5    0
30    500    5    5    5    5    5    0
250    5    5    5    5    5    0
31    500    5    5    3    5    5    0
250    5    5    4    5    5    0
32    500    5    5    5    5    5    0
250    5    5    5    5    5    0
33    500    5    5    5    5    5    0
250    5    5    5    5    5    0
34    500    5    5    5    5    5    0
250    5    5    5    5    5    0
35    500    5    5    5    5    5    0
250    5    5    5    5    5    0
36    500    5    5    5    5    5    0
250    5    5    5    5    5    0
37    500    5    5    5    5    5    0
250    5    5    5    5    5    0
38    500    5    5    5    5    5    0
250    5    5    5    5    5    0
39    500    5    5    5    5    5    0
250    5    5    5    5    5    0
40    500    5    5    5    5    5    0
250    5    5    5    5    5    0
41    500    5    5    5    5    5    0
250    5    5    5    5    5    0
续下
表6    续上
42    500    5    5    5    5    5    0
250    5    5    5    5    5    0
43    500    5    5    5    5    5    0
250    5    5    5    5    5    0
44    500    5    5    5    5    5    0
250    5    5    5    5    5    0
45    500    5    5    5    5    5    0
250    5    5    5    5    5    0
46    500    5    5    5    5    5    0
250    5    5    5    5    5    0
47    500    5    5    5    5    5    0
250    5    4    4    5    4    0
48    500    5    5    5    5    5    0
250    5    5    5    5    5    0
49    500    5    5    5    5    5    0
250    5    5    5    5    5    0
112    500    5    5    5    5    5    0
250    5    5    5    5    5    0
122    500    5    5    5    5    5    0
250    5    5    5    5    5    0
123    500    5    5    5    5    5    0
250    5    5    5    5    5    0
132    500    5    5    5    5    5    0
250    5    5    5    5    5    0
139    500    5    5    5    5    5    0
250    5    5    5    5    5    0
146    500    5    5    5    5    5    0
250    5    5    5    5    5    0
续下
表6    续上
147    500    5    5    5    5    5    0
250    5    5    5    5    5    0
152    500    5    5    5    5    5    0
250    5    5    5    5    5    0
165    500    5    5    5    5    5    0
250    5    5    5    5    5    0
169    500    5    5    5    5    5    0
250    5    5    5    5    5    0
176    500    5    5    5    5    5    0
250    5    5    5    5    5    0
191    500    5    5    5    5    5    0
250    5    5    5    5    5    0
248    500    5    5    5    5    5    0
250    5    5    5    5    5    0
262    500    5    5    5    5    5    0
250    5    5    5    5    5    0
265    500    5    5    5    5    5    0
250    5    5    5    5    5    0

Claims (2)

1、一种除草剂组合物，其特征在于它包括由以下通式(Ⅰ)表示的具有除草有效量的卤代乙酰胺化合物：
(Ⅰ)
式中：R1代表由C1-C6烷基，C1-C6烷氧基或卤素取代的或者未取代的苯基，由卤原子取代的或者未取代的噻吩基，或者由C1-C6烷基取代或者未取代的呋喃基，R2和R3彼此单独代表氢原子、甲基或乙基，
R4代表由C1-C6烷氧基，C2-C6链烯氧基或苯基取代的或者未取代的C1-C12烷基，或者由C1-C6烷基，C1-C4烷氧基或卤原子取代的或者未取代的苯基，Y代表氯，
以及农业上可接受的稀释剂或者载体；
卤代乙酰胺化合物的除草有效量为0.1-90%(重量)(按组合物的重量计)。
2、一种防治不需要植物生长的方法，其特征在于所述的方法包括将权利要求1所述的除草剂组合物施加到要求防治的场所，通式（Ⅰ）的卤代乙酰胺化合物的数量为2-3，000克/10公亩。
CN86104339A 1985-06-21 1986-06-21 以卤代乙酰胺化合物作为活性组分的除草剂组合物 Expired CN1015364B (zh)

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JP60134387A JPS61293956A (ja) 1985-06-21 1985-06-21 クロロアセトアミド化合物及びその製造方法
JP134387/85 1985-06-21

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US4895587A (en) 1990-01-23
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DE3660677D1 (en) 1988-10-13
EP0206251B1 (en) 1988-09-07
CN86104339A (zh) 1987-03-11
EP0206251A1 (en) 1986-12-30
JPH0515699B2 (zh) 1993-03-02

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