CN1104411C - (E)－O－酰基－α－氧代环十二酮肟,其制备方法和作为除草剂的用途 - Google Patents

(E)－O－酰基－α－氧代环十二酮肟,其制备方法和作为除草剂的用途 Download PDF

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CN1104411C
CN1104411C CN98100652A CN98100652A CN1104411C CN 1104411 C CN1104411 C CN 1104411C CN 98100652 A CN98100652 A CN 98100652A CN 98100652 A CN98100652 A CN 98100652A CN 1104411 C CN1104411 C CN 1104411C
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CN1227050A (zh
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王道全
侯学太
陈昶
梁晓梅
吴景平
吴学民
金淑惠
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China Agricultural University
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Abstract

本发明涉及化学结构新颖的通式为W的(E)-O-酰基-α-氧代环十二酮肟化合物及其合成方法以及制剂作为农用除草剂式中：X＝CH2，CH2CH2，CH＝CH，m＝1，0，Y＝氧原子，n＝1，0，R1，R2＝卤素，硝基，胺基，羟基，烷基，烷氧基，芳基通式为W的化合物由(E)α-氧代环十二酮肟与羧酸在二氯甲烷或氯仿溶剂中反应制得：式中X，Y，Z，m，n的含义同上。将通式为W的化合物溶于溶剂中，加入表面活性剂，如：农乳0208，GFC，OP-10，吐温-60等，按一定比例混匀配制成乳油或可湿性粉剂。通式为W的化合物及其制剂对马唐、稗草、油菜、绿豆、苋菜等具有抑制生长的作用，特别是对玉米和油菜表现出很好的触杀作用。

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(E)-O-酰基-α-氧代环十二酮肟，其制备方法和作为除草剂的用途
本发明涉及化学结构新颖的通式为W的(E)-O-酰基-α-氧代环十二酮肟化合物及其合成方法以及制剂作为农用除草剂式中：
X＝CH2，CH2CH2，CH＝CH，m＝1，0
Y＝氧原子，n＝1，0
R1，R2＝卤素，硝基，胺基，羟基，烷基，烷氧基，芳基
通式为W的化合物由(E)-α-氧代环十二酮肟与羧酸在二氯甲烷或氯仿溶剂中反应制得：
Figure C9810065200033
式中X，Y，Z，m，n的含义同上。
将通式为W的化合物溶于溶剂中，加入表面活性剂，如：农乳0208，GFC，OP-10，吐温-60等，按一定比例混匀配制成乳油或可湿性粉剂。
通式为W的化合物及其制剂对马唐、稗草、油菜、绿豆、苋菜等具有抑制生长的作用，特别是对玉米和油菜表现出很好的触杀作用。
本发明可用以下实例作进一步的说明，但本发明并不仅限于这些实例。实例1(E)-O-酰基-α-氧代环十二酮肟的制备
Figure C9810065200041
参考文献(Peter Yates，et al.，Tetrahedron，1981，37(19)，3357-3363)的程序进行。实例2化合物W4的合成
Figure C9810065200042
邻氯苯甲酸1.1g(0.007mol)，(E)-O-酰基-α-氧代环十二酮肟1.3g(0.006mol)及15ml无水二氯甲烷于50ml反应瓶中，搅拌使溶，然后加入DCC(二环己基碳二亚胺)1.5g(0.007mol)，室温下搅拌12小时。过滤除去不溶物。滤液依次用碳酸氢钠水溶液和饱和食盐水溶液洗涤，无水硫酸钠干燥，蒸除溶剂后得产物(E)-O-邻氯苯甲酰基-α-氧代环十二酮肟(W4)，经乙醇/水重结晶后得白色结晶，重1.7g，收率80％。m.p.86-88℃.δn(CDCl3)：0.96-1.96(m，16H)，2.76-3.08(m，4H)，7.8-7.92(m，4H)；IR(cm1)：2910，2850，1770，1700，1590，1470，1220，1090，1020，920，730；元素分析(测定值/计算值)：C 64.78/65.23，H 6.81/6.91，N 3.85/4.00
W系列其它化合物的合成均可按W4的操作程序进行，部分W系列化合物的物理常数及元素分析数据列入表1中。实例3化合物W4制剂的配制
在100ml容量瓶中加入化合物W4 20mg，用含10％乳化剂，1％渗透剂的溶剂溶解，然后用该溶剂定容。实例4W系列化合物的除草剂活性测定
施药方法：苗后施药，出苗后两片真叶期喷药
施药最：0.12Kg/ha
部分W系列化合物对玉米和油菜的除草活性列入表2中。
         表1W1-14的物理常数及其元素分析数据
         表2W1-14对玉米和油菜的除草活性(抑制率，％)
      (施药量0.12Kg/ha)
  编号              玉米            油菜
  W01W02W03W04W05W06W07W08W09W10W11W12W13W14   13.518.071.03.619.59.113.16.00.045.55.529.032.510.6   12.512.590.920.50.025.00.00.00.066.215.672.483.20.0

Claims (4)

1.下述通式W的(E)-O-酰基-α-氧代环十二酮肟化合物：
Figure C9810065200021
式中：
X＝CH2，CH2CH2，CH＝CH，m＝1，0
Y＝氧原子，n＝1，0
Figure C9810065200022
R1，R2＝卤素，硝基，胺基，羟基，烷基，烷氧基，芳基
2.权利要求1中所示化合物的合成方法，其特征是由(E)-α-氧代环十二酮肟与羧酸在二氯甲烷或氯仿溶剂中反应制得：
Figure C9810065200023
3.权利要求1的化合物配制成的乳油或可湿性粉剂。
4.权利要求1的化合物作为农用除草剂的应用。
CN98100652A 1998-02-27 1998-02-27 (E)－O－酰基－α－氧代环十二酮肟,其制备方法和作为除草剂的用途 Expired - Fee Related CN1104411C (zh)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4641320B1 (zh) * 1968-11-26 1971-12-06
JPS475245A (zh) * 1971-08-12 1972-03-16
US3843724A (en) * 1970-03-23 1974-10-22 Ciba Geigy Corp Carbamoyl oximes

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4641320B1 (zh) * 1968-11-26 1971-12-06
US3843724A (en) * 1970-03-23 1974-10-22 Ciba Geigy Corp Carbamoyl oximes
JPS475245A (zh) * 1971-08-12 1972-03-16

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
TETRAHEDRON 37(19) 1981-01-01 Peter Yates等 *

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