新型橙酮肟(醚)衍生物的合成及其除草活性

Synthesis and Herbicidal Activities of Novel Aurone Oxime (Ether) Derivatives

间苯二酚和氯乙腈经Houben-Hoesch反应制得2,4-二羟基-α-氯代苯乙酮(2);2与芳醛经环化和缩合反应制得6-羟基橙酮衍生物(4a^4e);4a^4e依次分别与一氯丙酮和NH2OR1·HCl反应合成了12个新型的橙酮肟(醚)衍生物(1a^1l),其结构经1H NMR,IR和元素分析的表征。初步的生物活性测试结果表明:在用药量为100μg·mL-1时,(Z)-2-(3-三氟甲基苯基)亚甲基-6-[(Z,E)-2-(乙氧基亚氨基)丙氧基]-3(2H)-苯并呋喃酮(1l)对油菜根长的生长抑制率为78.2%。

6-Hydroxylaurone derivatives（4a ～ 4e） were prepared by reaction of m-dihydroxybenzene with chloroacetonitrile,and then cyclization and condensation with aromatic aldehyde.Twelve novel aurone oxime（ether） derivatives （1a ～ 11） were synthesized by 4a ～ 4e with 1-chloroacetone and NH2OR1 · HCl,respectively.The structures were characterized by 1H NMR,IR and elemental analysis.The preliminary bioassay results showed that some of them displayed certain herbicidal activity.For example,inhibition of （Z）-2-（3-trifluoromethylphenyl） methylene-6-[（Z,E）-2-（ethoxy imino） propoxy]-3（2H）-benzofuranone（1l） was 78.2% against Brasica campestris at 100 μg· mL-1.