CN1151396A - 羟胺衍生物和含有羟胺衍生物的杀真菌剂 - Google Patents

羟胺衍生物和含有羟胺衍生物的杀真菌剂 Download PDF

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CN1151396A
CN1151396A CN96110126A CN96110126A CN1151396A CN 1151396 A CN1151396 A CN 1151396A CN 96110126 A CN96110126 A CN 96110126A CN 96110126 A CN96110126 A CN 96110126A CN 1151396 A CN1151396 A CN 1151396A
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zhi
haloalkyl
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安藤亘治
西口勉
远藤胜利
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Nihon Nohyaku Co Ltd
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Abstract

式(I)的羟胺衍生物：其中R表示基团或基团，其中R1和R2的定义见说明书，X表示CO2、CO或SO2，R3、R4、R5及R6代表氢原子或低级烷基，且n表示0或1，以及含此活性成分的杀真菌剂。本发明化合物具有优异的控制腐木真菌、植物疾病及人或动物真菌的作用，并可用作工业、农业及医药业杀真菌剂。

Description

羟胺衍生物和含有羟胺衍生物的杀真菌剂
本发明涉及式(I)表示的羟胺衍生物
Figure A9611012600081
其中R表示
Figure A9611012600082
基团或
Figure A9611012600083
基团，其中R1和R2相同或不同并且每个代表C1-C12烷基；C2-C7链烯基；C2-C7炔基；C3-C7环烷基；C1-C7卤代烷基；C2-C7卤代炔基；C1-C7烷氧基-C1-C7烷基；苯氧基C1-C7-烷基；环上取代有一至五个取代基的苯氧基C1-C7-烷基，取代基可相同或不同并选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基；C1-C7烷基硫基-C1-C7烷基；C1-C7烷基磺酰基-C1-C7烷基；氨基-C1-C7烷基，它取代有一至二个相同或不同的取代基，取代基选自C1-C7烷基和C3-C7环烷基；苯基；环上取代有一至五个相同或不同的取代基的苯基，取代基选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基；苄基；环上取代有一至五个相同或不同的取代基的苄基，取代基选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基；萘基；环上取代有一至七个相同或不同的取代基的萘基，取代基选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基；苯乙基；环上取代有一至五个相同或不同的取代基的苯乙基，取代基选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基；肉桂基；环上取代有一至五个相同或不同的取代基的肉桂基，取代基选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基；吡啶基；环上取代有一至四个相同或不同的取代基的吡啶基，取代基选自卤原子、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基；呋喃基；取代有一至三个相同或不同的取代基的呋喃基，取代基选自卤原子、硝基、氰基、C1-C7烷基；噻吩基；取代有一至三个相同或不同的取代基的噻吩基，取代基选自卤原子、硝基、氰基及C1-C7烷基，且
X表示CO2、CO或SO2，
R3、R4、R5及R6相同或不同并且每个代表氢原子或C1-C7烷基，且
n表示0或整数1，以及
含此活性成分的杀真菌剂。
关于羟胺衍生物，日本专利文献昭47-43829(JP-B-47829(1972))描述了式(A)表示的化合物：作为杀虫剂和杀螨剂。日本专利申请公开号昭55-36498(JP-B-5536498(1980))描述了式(B)表示的化合物：
Figure A9611012600112
作为具有抗除草剂的植物毒性活性的植物保护剂。但是，还不这些化合物具有杀真菌活性。
本发明涉及新的羟胺衍生物及含此衍生物作为活性成分的杀真菌剂。
本发明者为了发现一种新的杀真菌剂进行了刻苦的研究，并随之发现本发明式(I)表示的羟胺衍生物具有强杀真菌活性并可作为有用的农业、工业及医药业杀真菌剂。此发现导致了本发明的完成。
在式(I)的R1及R2的定义中，C1-C12烷基的实例包括含1至12个碳原子的直链或支链烷基，如甲基、乙基、正丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、1-乙基-正戊基、正己基、2-乙基-正己基及正癸基。
C2-C7链烯基的实例包括含2至7个碳原子的链烯基，如乙烯基、1-丙烯基、2-丙烯基、1-甲基-2-丙烯基、1，1-二甲基-2-丙烯基、丁烯基、戊烯剂及己烯剂。
C2-C7炔基的实例包括含2至7个碳原子的炔基，如乙炔基、2-丙炔基、1-甲基-2-丙炔基、1，1-二甲基-2-丙炔基、丁炔基、戊炔基及己炔基。
C3-C7环烷基的实例包括含3至7个碳原子的环烷基，如环丙基、环丁基、环戊基及环己基。
C1-C7卤代烷基的实例包括取代有一个或多个相同或不同的卤原子的含1至7个碳原子的烷基，如氯甲基、溴甲基、碘甲基、氟甲基、二氟甲基、三氟甲基、1，1，1-三氯乙基、2，2，2-三氟乙基、1，1，1，2，2-五氟乙基、氯丙基、氟丁基、氯戊基及氟己基。
C2-C7卤代炔基的实例包括取代有一个或多个相同或不同的卤原子的含2至7个碳原子的炔基，如3-氯-2-丙炔基、3-氟-2-丙炔基、2-氯丙炔基、2-氟丙炔基、4-氯-2-丁炔基基4-氟-2-丁炔基。
C1-C7烷氧基-C1-C7烷基的实例包括如甲氧基甲基、甲氧基乙基、乙氧基甲基、乙氧基乙基、甲氧基丙基及乙氧基丁基的烷氧基-烷基。
苯氧基-C1-C7烷基的实例包括如苯氧基甲基、苯氧基乙基、苯氧基丙基及苯氧基丁基的苯氧基-烷基。
C1-C7烷基硫基-C1-C7烷基的实例包括如甲基硫基甲基、甲基硫基乙基、乙基硫基甲基、乙基硫基乙基、甲基硫基丙基及乙基硫基丁基的烷基硫基烷基。
C1-C7烷基磺酰基-C1-C7烷基的实例包括如甲基磺酰基甲基、甲基磺酰基乙基、乙基磺酰基甲基、乙基磺酰基乙基、甲基磺酰基丙基和乙基磺酰基丁基的烷基磺酰基烷基。
具有一个或两个相同或不同的选自烷基或环烷基取代基的氨基烷基的实例包括如甲基氨基甲基、乙基氨基甲基、二甲基氨基甲基、二乙基氨基甲基、二甲基氨基乙基、二乙基氨基乙基、N-甲基-N-乙基氨基甲基、N-甲基-N-乙基氨基乙基、环丙基-氨基甲基和环己基氨基乙基的氨基烷基。
取代的苯氧基C1-C7烷基、取代的苯基、取代的萘基、取代的苄基、取代的苯乙基及取代的肉桂基的取代基的实例包括卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一或二个相同或不同的C1-C7烷基的氨基。
取代的吡啶基的取代基的实例包括卤原子、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基。
取代的呋喃基的取代基的实例包括卤原子、硝基、氰基和C1-C7烷基。
C1-C7烷基的实例包括含1至7个碳原子的烷基，如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基及正己基。
C1-C7卤代烷基的实例包括取代有一个或多个相同或不同的卤原子取代基的含1至7个碳原子的烷基，如氯甲基、溴甲基、碘甲基、氟甲基、二氟甲基、三氟甲基、氯甲基、1，1，1，2，2-五氟乙基、氯丙基及氟丙基。
C1-C7烷氧基的实例包括含1至7个碳原子的烷氧基，如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、叔丁氧基、正戊氧基和正己氧基。
C1-C7卤代烷氧基的实例包括含1至7个碳原子的烷氧基，如氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、1-氯乙氧基、二氯乙氧基、氯丙氧基、氟丙氧基、氯丁氧基及氟丁氧基。
C1-C7烷氧基羰基的实例包括含1至7个碳原子的烷氧基羰基，如甲氧基羰基、乙氧基羰基、正丙氧基羰基、异丙氧基羰基和正丁氧基羰基。
C1-C7烷基硫基的实例包括含1至7个碳原子的烷基硫基，如甲基硫基、乙基硫基、正丙基硫基、异丙基硫基、正丁基硫基、异丁基硫基、叔丁基硫基、正戊基硫基及正己基硫基。
C1-C7卤代烷基硫基的实例包括取代有一个或多个相同的或不同的卤原子的含1至7个碳原子的烷基硫基，如氯甲基硫基、溴甲基硫基、碘甲基硫基、氟甲基硫基、二氟甲基硫基、三氟甲基硫基、氯乙基硫基、1，1，1，2，2-五氟乙基硫基、氯丙基硫基及氟丙基硫基。
C1-C7烷基磺酰基的实例包括含1至7个碳原子的烷基磺酰基，如甲基磺酰基、乙基磺酰基、正丙基磺酰基、异丙基磺酰基、正丁基磺酰基、异丁基磺酰基、仲丁基磺酰基、叔丁基磺酰基、正戊基磺酰基及正己基磺酰基。
C1-C7卤代烷基磺酰基的实例包括含1至7个碳原子的烷基磺酰基，它有一个或多个相同或不同的选自卤原子的取代基，如氯甲基磺酰基、溴甲基磺酰基、碘甲基磺酰基、氟甲基磺酰基、二氟甲基磺酰基、三氟甲基磺酰基、氯乙基磺酰基、1，1，1，2，2-五氟乙基磺酰基、氯丙基磺酰基和氟丙基磺酰基。
由一个或两个相同或不同的C1-C7烷基取代的氨基的实例包括如甲基氨基、乙基氨基、二甲基氨基、二乙基氨基、二丙基氨基、二丁基氨基、N-甲基-N-乙基氨基和N-甲基-N-乙基氨基的氨基。
优选R表示 基团，R1表示甲基，R2表示C1-C7烷基、苯基、有一个或多个相同或不同的取代基的苯基(其中取代基选自卤原子或C1-C7烷基)苄基或有一个或多个相同或不同取代基的苄基(其中取代基选自卤原子或C1-C7烷基)，
X表示CO或CO2，R3、R4、R5及R6都代表氢原子，且
n表示0或整数1。
(1)当X是CO2或SO2时：
Figure A9611012600163
其中R1、R2、R3、R4、R5、R6和n的定义与上述限定相同，且X表示CO2或SO2，Hal表示卤原子。
即在惰性溶剂中，在碱的存在下，在室温至回流的温度用式(III)化合物处理式(II)化合物得到式(VIa)的化合物。然后，式(VIa)化合物在惰性溶剂中，在碱及碘化试剂如碘、一氯化碘、碘-吗啉复合物或N-碘化琥珀酰胺的存在下，在约0℃至室温反应，由此得到式(Ia)的化合物。(2)当X是CO时：
Figure A9611012600172
其中R1、R2、R3、R4、R5、R6、n及Hal的定义与上述限定相同。
即可通过用式(III)的化合物在碱的存在下用与(1)相同的方式处理式(II′)的化合物得到式(VIb)及式(VIc)的混合物。通过柱色谱等方法将式(VIb)及式(VIc)的化合物分离，如(1)进行碘化反应，可制备式(Ib)和式(Ic)的羟胺衍生物。
式(VIc)的化合物可按如下示意图制备：其中R1、R2、R3、R4、R5、R6、n及Hal的定义与上述限定相同。
即可通过将式(II′)化合物与如五氯化磷等卤化试剂反应，然后将所得的式(V)的化合物与式(VI)的化合物在惰性溶剂中在室温至惰性溶剂回流的温度下反应制备式(VIc)的化合物。
每个反应中使用的碱包括无机碱及有机碱。其适当的实例包括氢氧化钠、氢氧化钾、碳酸钾、甲醇钠基氢化钠。这些碱的用量等于或大于式(V)的化合物的摩尔数。
如果它不抑制反应，则任何惰性溶剂都是合适的。惰性溶剂的实例包括酮如丙酮、甲基乙基酮及环己酮；线型或环醚如乙醚、异丙醚、二甲氧基乙烷、四氢呋喃、二噁烷、甘醇单甲醚和甘醇二甲醚；酯如乙酸甲酯和乙酸乙酯；卤代烃如二氯乙烷、氯仿、四氯化碳基四氯乙烷；芳香烃如苯、氯苯、硝基苯、甲苯及二甲苯；腈如乙腈；醇如甲醇、乙醇及异丙醇；二甲基甲酰胺；二甲亚砜；水；及其混合物。当使用水和不溶于水的惰性溶剂进行两相反应时，可使用相转移催化剂。相转移催化剂的实例包括氯化三乙基苄基铵和氯化三辛基甲基铵。因为每个反应都是等摩尔反应，故优选使用等摩尔的试剂。但在一个反应中可使用较大量的试剂。
本发明式(I)的羟胺衍生物可用作农业、工业及医药业杀真菌剂。作为农业用杀真菌剂，羟胺衍生物可特别用于控制水稻的稻疫病(Pyricularia oryzae)、黄瓜的霜霉(古巴假霜霉)、西红柿的晚疫病(蔓延疫霉)、葡萄的褐斑病(芽枝状枝孢)、水稻的籽枯萎病(绿色木霉)、苹果的链格菌属brotch(苹果火星病链格孢)、甜薯的干腐病(尖孢镰孢)、洋葱的黑霉病(黑色曲霉)、甜薯的软腐病(黑色根霉)、水稻的恶苗病(稻恶苗赤霉)、大麦及小麦的白粉菌(禾白粉菌)、黄瓜的白粉菌(苍耳单囊壳)、苹果的白粉菌(苹果白粉病柄球菌)、葡萄的白粉菌(葡萄白粉病钩丝壳霉)、其它寄生植物的白粉菌、小麦的叶锈病(隐匿柄锈菌)、燕麦的冠锈病(禾冠柄锈菌)以及其它寄生植物的锈菌。羟胺衍生物特别可用作种子消毒剂。
作为工业用杀真菌剂，羟胺衍生物具有杀菌活性，特别是对腐木菌如瘤盖干酪菌、杂色革盖菌及Selupula lacrymas，并可用作胶合板、木制品及木质制品如刨花板和纤维板的木材防腐剂，用作纸浆用水、塑料制品及油漆的防腐剂和杀真菌剂，用作化妆品及皮革制品的防腐剂并可用作衣料的杀真菌剂。
作为医药业用杀真菌剂，羟胺衍生物可用于人及动物四肢的消毒及治疗发癣菌属、假丝酵母属、曲霉属等引起的表皮真菌感染、粘膜感染及系统真菌感染。
含有本发明式(I)羟胺衍生物作为活性成分的农业及工业杀真菌剂可以适当的制剂形式使用。例如，活性成分以适当的量与适当的惰性载体及(如需要)赋形剂混合进行溶解、分散、混悬、混合、浸泡、吸附或吸收，且混合物可配制成溶液、混悬液、油、乳液、粉剂、颗粒剂、可湿的粉末、可湿的颗粒、颗粒沉淀、软膏、气雾剂等。
可用于本发明的惰性载体可以是固体、液体或气体。固体载体的实例包括黄豆粉、木粉、树皮粉、锯末、烟草茎粉、核桃壳粉、麦麸粉、纤维粉、食物提取后得到的残余物、合成聚合物如粉状合成树脂、粘土(例如，高岭土、皂土和酸性粘土)、滑石类(例如，滑石和叶蜡石)、硅石(例如，硅藻土、石英砂、云母、合成硅酸盐基高分散性合成硅酸)、活性炭、硫粉、浮石、煅烧的硅藻土、砖粉、飘尘、砂、碳酸钙或磷酸钙的无机盐粉、硫酸铵、磷酸铵、硝酸铵、氯化铵或尿素的化肥或堆肥。这些可单独或联合使用。
液体载体包括一种本身具有溶剂作用及一种无溶剂作用但可用辅剂将活性成分分散的液体。液体载体的实例包括水；醇如甲醇、异丙醇和甘醇；酮如丙酮和环己酮；醚如乙醚、二噁烷、四氢呋喃基溶纤剂；脂肪烃如汽油和煤油；芳香烃如苯、甲苯、溶剂萘和甲基萘；卤代烃如二氯乙烷和氯仿；酯如乙酸乙酯和邻苯二甲酸二异丙酯；酰胺如二甲基甲酰胺和二甲基乙酰胺；腈如乙腈；及二甲基亚砜。这些化合物可单独或联合使用。
气体载体的实例包括氟利昂、丁烷气体、甲醚、二氧化碳和LPG(液化汽油气)。
按照本发明目的使用辅剂。用表面活性剂可乳化、分散、溶解或湿润活性成分化合物。表面活性剂的实例包括聚氧乙烯烷基芳基醚、聚氧乙烯烷基醚、聚氧乙烯高级脂肪酸酯、聚氧乙烯树脂酸酯、聚氧乙烯脱水山梨醇单油酸酯、烷基烯丙基脱水山梨醇单月桂酸酯、烷基苯磺酸盐、烷基萘磺酸盐、木素磺酸盐及高级醇磺酸酯。这些可单独或联合使用。在一些例子中，不使用辅剂。
可使用辅剂稳定活性成分化合物的分散液并粘附或结合活性成分化合物。这样的辅剂的实例包括酪蛋白、明胶、淀粉、藻酸、CMC、阿拉伯树胶、琼脂、聚乙烯醇、木材松节油、稻麸油、皂土、木素及亚硫酸盐废液。
可使用辅剂改善固体产品的流动性。这样的辅剂的实例包括蜡、硬脂酸及烷基磷酸盐。
辅剂可用作可分散产品的溶胶剂(抗絮凝剂)。这样的辅剂的实例包括萘磺酸缩合物及磷酸盐。
也可添加消泡剂如硅油。
当本发明式(I)的羟胺衍生物用作农业和园艺用杀真菌剂时，活性成分的量取决于多种因素如目的、庄稼、庄稼的生长条件、疾病出现的途径、天气、环境条件、制剂、使用方法、使用位置、使用时间等。但选择0.1g至1kg每英亩的范围是合适的。
活性成分的用量可根据需要调整。对于粉尘或粉末，一般为0.5至20％。对于乳化的浓缩物、混悬液或可湿的粉末，为0.1至90％。
为了扩大可控制疾病的范围、延长控制的时间并降低化学试剂的用量，本发明的农业和园艺用杀虫剂也可通过与其它农业和园艺用杀真菌剂混合使用。含有本发明化合物作为活性成分的农业和园艺用杀真菌剂对上述破坏稻谷庄稼、旱地庄稼、果树、蔬菜、其它庄稼、花卉等的疾病具有显著的杀菌活性。因此，在疾病出现前或出现时将这些杀真菌剂施于水、叶(茎和叶)及种植稻田作物、旱地作物、果树、蔬菜、其它庄稼、花卉等的土壤中，使本发明的杀真菌剂产生所需的效果。
当本发明的式(I)的羟胺衍生物用作木材防腐剂时，通过涂抹、喷洒、浸泡等手段对锯材进行表面处理或用加压注射、真空注射等手段处理，防腐剂用原液或用水等稀释。此外，通过向胶合板粘合剂中添加羟胺衍生物，可将本发明的羟胺衍生物用于建筑材料中，特别是作为防止腐木真菌的试剂。
化学试剂的量一般随制剂的类型、使用的时间、使用位置、使用方法、腐木真菌的类型、破坏的程度等因素而变化。含此化学成分的化学试剂的一般用量为0.1至40g每平方米锯材。
当本发明的羟胺衍生物用作木材防腐剂时，它们可与其它木材防腐剂、杀虫剂、杀螨剂、杀蚁剂、消毒剂及增效剂混合使用。普通木材防腐剂的实例包括3-碘-2-丙炔基丁基氨基甲酸酯、3-碘炔丙基及环烷酸锌。杀蚁剂的实例包括Chlorpyrifos、Phoxim、杀螟松、苄氯菊酯、cypermethrin及fenvalerate。
当本发明式(I)的羟胺衍生物用作医药业杀真菌剂时，它们可单独或以含有药用惰性载体或稀释剂的组合物的形式使用，取其适于口服或非肠道给药的形式，如液体、片剂、栓剂、乳剂、软膏、霜剂、洗剂或糊剂(泥罨剂)。制剂中可含有辅剂、稳定剂、湿润剂、乳化剂、缓冲剂及其它普通添加剂。在全身性治疗中，此化合物可以以0.05至100mg(优选0.5至50mg)成人每天每公斤体重给药。在局部治疗中活性成分的适当浓度为0.001至5％，优选0.1至2％。
实施例
通过下列实施例、制剂实施例及试验实施例对本发明进行特别的说明。但本发明不限于此。实施例1  N-甲氧基-N-碘炔丙基氨基甲酸甲酯(化合物1)的制备
将0.43g氢化钠(60％油中)悬浮于10ml四氢呋喃中，用冰冷却的同时按顺序向悬液中加入1.0gN-甲氧基氨基甲酸甲酯和1.36g炔丙基溴。将混合物加热回流4小时。反应完成后，向反应溶液中加入水，用乙酸乙酯萃取混合物。将萃取物干燥、浓缩并通过硅胶柱色谱纯化，得到0.8gN-甲氧基-N-炔丙基氨基甲酸甲酯。
将所得0.5g N-甲氧基-N-炔丙基氨基甲酸甲酯加入到5mlN，N-二甲基甲酰胺中，向其中加入1.8g碘和含催化量的碘化钾饱和水溶液的5ml N，N-二甲基甲酰胺。用冰冷却的同时滴加2.0g 30％氢氧化钾水溶液。将混合物在室温搅拌2小时。反应完成后，向反应液中加入水，并用乙酸乙酯萃取混合物。用硫代硫酸钠饱和水溶液及水洗涤萃取物，并干燥浓缩得到0.6g N-甲氧基-N-碘炔丙基氨基甲酸甲酯。
1H-NMR(δin CDCl3)3.78(s；3H)，3.81(s；3H)，
                    4.39(s；2H)实施例2  N-甲氧基-N-碘炔丙基氧甲基氨基甲酸甲酯(化合物94)的制备
将0.37g氢化钠(60％油中)悬浮于10ml四氢呋喃中，用冰冷却的同时按顺序向悬液中加入0.8gN-甲氧基氨基甲酸甲酯和0.96g氯甲基炔丙基醚。将混合物加热回流1小时。反应完成后，向反应溶液中加入水，用乙酸乙酯萃取混合物。将萃取物干燥、浓缩并通过硅胶柱色谱纯化，得到1.0gN-甲氧基-N-炔丙基氧甲基氨基甲酸甲酯。
将所得0.5gN-甲氧基-N-炔丙基氧甲基氨基甲酸甲酯加入到5mlN，N-二甲基甲酰胺中，向其中加入1.5g碘和5ml含催化量的碘化钾饱和水溶液的N，N-二甲基甲酰胺，用冰冷却的同时加入1.6g30％氢氧化钾水溶液。将混合物在室温搅拌2小时。反应完成后，向反应液中加入水，并用乙酸乙酯萃取混合物。用硫代硫酸钠饱和水溶液及水洗涤萃取物，并干燥、浓缩得到0.7gN-甲氧基-N-碘炔丙基氧甲基氨基甲酸甲酯。
1H-NMR(δin CDCl3)3.78(s；3H)，3.82(s；3H)，
                    4.42(s；2H)，5.04(s；2H)实施例3  N-甲氧基-N-碘炔丙基-对-氯苯甲酰胺(化合物57)的制备
将0.22g氢化钠(60％油中)悬浮于10ml四氢呋喃中，用冰冷却的同时按顺序向溶液中加入1.0gN-甲氧基-对-氯苯甲酰胺和0.68g炔丙基溴。将混合物加热回流8小时。反应完成后，向反应溶液中加入水，用乙酸乙酯萃取混合物。将萃取物干燥、浓缩并通过硅胶柱色谱纯化，得到0.44gN-甲氧基-N-炔丙基-对-氯苯甲酰胺。
将所得0.44gN-甲氧基-N-炔丙基-对-氯苯甲酰胺加入到5mlN，N-二甲基甲酰胺中，向溶液中加入1.5g碘和5ml含催化量的碘化钾饱和水溶液的N，N-二甲基甲酰胺，用冰冷却的同时加入1.8g30％氢氧化钾水溶液。将混合物在室温搅拌2小时。反应完成后，向反应液中加入水，并用乙酸乙酯萃取混合物。用硫代硫酸钠饱和水溶液及水洗涤萃取物，并干燥、浓缩得到0.47gN-甲氧基-N-碘炔丙基-对-氯苯甲酰胺。
1H-NMR(δin CDCl3)3.67(s；3H)，4.66(s；2H)，
                    7.40(d；2H)，7.69(d：2H)实施例4  碘炔丙基N-甲氧基-2，4-二氯苯甲酰亚胺(化合物130)的制备
将1.0gN-甲氧基-2，4-二氯苯甲酰胺、0.75g碳酸钾及0.65g炔丙基溴加入到10mlN，N-二甲基甲酰胺中，将混合物搅拌3小时。反应完成后，向反应液中加入水，用乙酸乙酯萃取混合物。将萃取物干燥、浓缩并通过硅胶柱色谱纯化，得到0.35g炔丙基N-甲氧基-2，4-二氯苯甲酰亚胺。
将所得0.35g炔丙基N-甲氧基-2，4-二氯苯甲酰亚胺溶于5mlN，N-二甲基甲酰胺中，向其中加入1.0g碘和5ml含催化量的碘化钾饱和水溶液的N，N-二甲基甲酰胺，用冰冷却的同时加入1.3g30％氢氧化钾水溶液。将混合物在室温搅拌1小时。反应完成后，向反应液中加入水，并用乙酸乙酯萃取混合物。用硫代硫酸钠饱和水溶液及水洗涤萃取物，并干燥、浓缩得到0.47g碘炔丙基N-甲氧基-2，4-二氯苯甲酰亚胺。
1H-NMR(δin CDCl3)3.93(s；3H)，4.73(s；2H)，
                         7.3-7.5(m；3H)实施例5  碘炔丙基N-甲氧基-对-氯苯甲酰亚胺(化合物125)的制备
将1.0gN-甲氧基-对-氯苯甲酰胺溶于10ml四氯化碳中，并向其中加入1.2g四氯化磷，将混合物回流3小时。用水洗涤反应溶液、干燥、浓缩得到0.61g4，α-二氯苯甲醛肟O-甲基醚。
将0.18g炔丙基醇溶于5ml四氢呋喃中，在冰冷却的同时向其中加入0.13g氢化钠(60％油中)。向其中滴加5ml四氢呋喃中的0.61g4，α-二氯苯甲醛肟O-甲基醚。混合物加热回流6小时。然后向反应液中加入水，用乙酸乙酯萃取混合物。将萃取物干燥、浓缩，并通过硅胶柱色谱纯化，得到0.59丙炔基N-甲氧基-对-氯苯甲酰亚胺。
将所得0.59丙炔基N-甲氧基-对-氯苯甲酰亚胺溶于5mlN，N-二甲基甲酰胺中，向其中加入2.0g碘和5ml含催化量的碘化钾饱和水溶液的N，N-二甲基甲酰胺，用冰冷却的同时滴加2.5g30％氢氧化钾水溶液。将混合物在室温搅拌3小时。反应完成后，向反应液中加入水，并用乙酸乙酯萃取混合物。用硫代硫酸钠饱和水溶液及水洗涤萃取物，并干燥、浓缩得到0.78g碘炔丙基N-甲氧基-对-氯苯甲酰亚胺。
1H-NMR(δin CDCl3)3.92(s；3H)，5.10(s；2H)，
                    7.34(d；2H)，7.69(d；2H)实施例6  N-甲氧基-N-碘炔丙基-氧甲基苯甲酰胺(化合物103)的制备
将0.6gN-甲氧基苯甲酰胺溶于10ml乙腈中，并向其中顺序加入0.55g碳酸钾及0.42g氯甲基炔丙基醚。将混合物室温搅拌3小时。反应完成后，向反应中加入水，用乙酸乙酯萃取混合物。将萃取物干燥、浓缩，并通过硅胶柱色谱纯化，得到0.8gN-甲氧基-N-炔丙基氧甲基苯甲酰胺。
将所得0.8gN-甲氧基-N-炔丙基氧甲基苯甲酰胺溶于5ml甲醇中，并向其中加入0.85g30％氢氧化钠水溶液。在用冰冷却的同时向其中滴加5ml甲醇中的0.41g一氯化碘，将混合物在室温搅拌1小时。反应完成后，向反应液中加入水，并用乙酸乙酯萃取混合物。用硫代硫酸钠饱和水溶液及水洗涤萃取物，并干燥、浓缩得到0.7gN-甲氧基-N-碘炔丙基氧甲基苯甲酰胺。1H-NMR(δin CDCl3)3.93(s；3H)，4.58(s；2H)，
                5.40(s；2H)，7.3-7.5(m；3H)
                7.6-7.8(m；2H)实施例7  N-甲氧基-N-碘炔丙基-氧甲基苯磺酰胺(化合物118)的制备
将0.6gN-甲氧基苯磺酰胺溶于10ml乙腈中，并向其中顺序加入0.44g碳酸钾及0.34g氯甲基炔丙基醚。将混合物室温搅拌4小时。反应完成后，向反应中加入水，用乙酸乙酯萃取混合物。将萃取物干燥、浓缩，并通过硅胶柱色谱纯化，得到0.7gN-甲氧基-N-炔丙基氧甲基苯磺酰胺。
将所得0.5gN-甲氧基-N-炔丙基氧甲基苯磺酰胺溶于5mlN，N-二甲基甲酰胺中，向其中加入1.5g碘和5ml含催化量的碘化钾饱和水溶液的N，N-二甲基甲酰胺，用冰冷却的同时向其中滴加1.8g30％氢氧化钾水溶液。将混合物在室温搅拌3小时。反应完成后，向反应液中加入水，并用乙酸乙酯萃取混合物。用硫代硫酸钠饱和水溶液及水洗涤萃取物，干燥并浓缩得到0.6gN-甲氧基-N-碘炔丙基氧甲基苯磺酰胺。1HMR-NMR(δin CDCl3)3.89(s；3H)，4.31(s；2H)，
                  4.70(s；2H)，7.5-8.0(m；5H)
本发明化合物的典型实例示于表1中，按实施例1-7中的相同方法制备。但是，本发明并不限于此。在表1中，Ph表示苯基，c-C3H5表示环丙基，c-C6H11代表环己基。折射率后括号中数字指的是温度(℃)。
                              表1a
Figure A9611012600301
No.  R1                  R2         X       n     物理性质(*)1    CH3                 CH3        CO2    0    nD1.535(20℃)2    i-C3H7             CH3        CO2    0    nD1.507(17℃)3    3-Cl(CH2)3         CH3        CO2    04    H2C＝CHCH2         CH3        CO2    0    nD1.526(17℃)5    HC≡CCH2            CH3        CO2    06    IC≡CCH2            CH3        CO2    07    n-C4H9             CH3        CO2    0    nD1.514(16℃)8    i-C4H9             CH3        CO2    09    c-C6H11            CH3        CO2    010    C2H5OCH2CH2     CH3        CO2    0    nD1.517(16℃)11    C2H5SCH2CH2     CH3        CO2    012    C2H5SO2CH2CH2  CH3        CO2    013    n-C12H25            CH3        CO2    0    nD1.486(13℃)14    Ph                    CH3        CO2    015    PhCH2                CH3        CO2    0    nD1.571(16℃)16    CH3                  FCH2CH2   CO2    017    CH3                  ClCH2CH2  CO2    0
                 表1a(续)No.   R1                R2                  X       n    物理性质(*)18    CH3               c-C3H5            CO2    019    CH3               n-C4H9            CO2    0    nD1.508(26℃)20    CH3               i-C4H9            CO2    0    nD1.498(18℃)21    CH3               c-C6H11           CO2    022    CH3               n-C12H25          CO2    023    CH3               2-C2H5-n-C6H11 CO2    0    nD1.483(26℃)24    CH3               CCl3CH2          CO2    0    nD1.546(18℃)25    CH3               CF3CH2           CO2    026    CH3               CH3OCH2CH2      CO2    0    nD1.478(20℃)27    CH3               PhOCH2CH2        CO2    028    CH3               CH3SCH2CH2      CO2    029    CH3               CH3SO2CH2CH2  CO2    030    CH3               Ph                 CO2    031    CH3               PhCH2             CO2    032    n-C4H9          i-C4H9           CO2    0    nD1.487(20℃)33    C2H5OCH2CH2  i-C4H9           CO2    0    nD1.493(17℃)34    PhCH2            i-C4H9           CO2    0    nD1.538(20℃)35    4-Cl-PhCH2       CH3               CO2    0    nD1.568(25℃)36    4-CH3-PhCH2     CH3               CO2    0    nD1.562(25℃)37    PhCH2CH2        CH3               CO2    0    nD1.548(25℃)38    PhCH＝CHCH2      CH3               CO2    0    nD1.586(25℃)39    CH3              n-C3H7           CO      0    nD1.524(13℃)
                  表1a(续)No.   R1     R2                    X    n     物理性质(*)40    CH3    c-C3H5              CO    0    nD1.546(26℃)41    CH3    3-Cl(CH2)3          CO    042    CH3    i-C4H9              CO    0    nD1.507(24℃)43    CH3    n-C5H11             CO    0    nD1.512(26℃)44    CH3    1-C2H5-n-C5H10   CO    0    nD1.513(24℃)45    CH3    n-C7H15             CO    0    nD1.501(26℃)46    CH3    C≡CH                 CO    047    CH3    C≡CI                 CO    048    CH3    CH2OC2H5          CO    049    CH3    CH2SC3H7-n        CO    050    CH3    CH2SO2C3H7-n     CO    051    CH3    CH2N(CH3)2        CO    052    CH3    Ph                    CO    0    m.p.83-86℃53    CH3    4-NO2-Ph             CO    0    糊状54    CH3    2-CO2CH3-Ph        CO    0    nD1.576(21℃)55    CH3    2-CF3-Ph            CO    0     nD1.526(24℃)56    CH3    2-Cl-Ph              CO    0     m.p.93-94℃57    CH3    4-Cl-Ph              CO    0     m.p.100-101℃58    CH3    4-Br-Ph              CO    0     nD1.615(19℃)59    CH3    4-F-Ph               CO    0     nD1.571(19℃)60    CH3    4-CH3-Ph            CO    0     nD1.574(21℃)61    CH3    4-t-C4H9-Ph        CO    0     nD1.563(15℃)
                 表1a(续)No.   R1     R2                 X     n   物理性质(*)62    CH3    4-CH3O-Ph          CO    0   paste63    CH3    2，6-F2-Ph         CO    0   nD1.532(25℃)64    CH3    4-CH3S-Ph          CO    065   -CH3    4-CH3SO2-Ph      CO    066    CH3    4-CF3-Ph          CO    067    CH3    4-CF3O-Ph         CO    068    CH3    4-CN-Ph            CO    069    CH3    4-PhO-Ph           CO    070    CH3    4-(CH3)2N-Ph    CO    071    CH3    2，4-Cl2-Ph      CO    0    m.p.156-157℃72    CH3    3，5-Cl2-Ph      CO    0    nD1.589(21℃)73    CH3    2-naphthyl        CO    074    CH3    2-pyridyl         CO    075    CH3    3-pyridyl         CO    0    m.p.110-115℃76    CH3    4-pyridyl         CO    077    CH3    2-furyl           CO    0    m.p.92-93℃78    CH3    2-thienyl         CO    0    m.p.83-85℃79    CH3    PhCH2            CO    0    nD1.578(24℃)80    CH3    4-Cl-PhCH2       CO    081    CH3    4-CH3-PhCH2     CO    082    CH3    PhOCH2           CO    0    nD1.591(24℃)83    CH3    4-Cl-PhOCH2      CO    0
                      表1a(续)No.    R1             R2                    X      n    物理性质(*)84    CH3            2，4-Cl2-PhOCH2     CO     085    n-C4H9        n-C3H7              CO     0   nD1.518(25℃)86    i-C4H9        n-C3H7              CO     087    c-C6H11       n-C3H7              CO     0    -88    (CH3)2NCH2  n-C3H7              CO     089    Ph              CH3                  CO     090    PhCH2          n-C3H7             CO     0    nD1.564(13℃)91    PhCH2          t-C4H9             CO     0    nD1.547(14℃)92    PhCH2          CH2OC2H5          CO     093    PhCH2          Ph                    CO     0    nD1.608(15℃)94    CH3            CH3                 CO2   1    nD1.510(16℃)95    CH3            i-C4H9             CO2   1    nD1.492(22℃)96    CH3            CCl3CH2            CO2   1    nD1.534(22℃)97    n-C4H9        i-C4H9             CO2   1    nD1.498(22℃)98    C2H5OCH2CH2CH3                 CO2   1    nD1.505(22℃)99    PhCH2          CH3                 CO2   1    nD1.537(22℃)100    PhCH2          i-C4H9             CO2   1    nD1.533(22℃)101    CH3            c-C3H5             CO     1102    CH3            3-Cl(CH2)3         CO     1    nD1.527(21℃)103    CH3            Ph                    CO     1    nD1.509(28℃)104    CH3            2-Cl-Ph               CO     1    nD1.574(21℃)105    CH3            4-Cl-Ph               CO     1    nD1.581(21℃)
                表1a(续)No.    R1     R2            X     n     物理性质(*)106    CH3    4-F-Ph         CO    1107    CH3    4-CH3-Ph      CO    1    nD1.571(21℃)108    CH3    4-NO2-Ph      CO    1    m.p.98-100℃109    CH3    3，5-Cl2-Ph   CO    1    m.p.52-53℃110    CH3    2，6-F2-Ph    CO    1    糊状111    CH3    PhCH＝CHCH2   CO    1112    CH3    n-C5H11      CO    1    nD1.560(28℃)113    CH3    n-C7H15      CO    1    nD1.507(15℃)(*熔点或折射率)
                      表1bNo.   R1     R2        R3  R4  R5    R6   X     n    物理性质(*)114   CH3    i-C4H9   H    H    CH3   CH3  CO2  1    nD1.489(16℃)115   CH3    4-Cl-Ph     H    H    CH3   CH3  CO    1    nD1.548(21℃)116   CH3    4-Cl-Ph     CH3 H    H      H     CO    1117   CH3    Ph          H    H    H      H     SO2  0    糊状118   CH3    Ph          H    H    H      H     SO2  1    nD1.550(28℃)119   CH3    4-CH3-Ph   H    H    H      H     SO2  0    m.p.57-58℃(*熔点或折射率)
           表1c在式(I)中，R3＝R4＝R5＝R6＝H，n＝0
                                物理性质No.    R1         R2           (熔点或折射率)120    CH3        Ph             nD1.585(28℃)121    n-C3H7    Ph122    i-C4H9    Ph123    PhCH2CH2  Ph124    CH3        2-Cl-Ph        nD1.593(19℃)125    CH3        4-Cl-Ph        nD1.584(17℃)126    CH3        4-Br-Ph        m.p.56-57℃127    CH3        4-F-Ph         nD1.576(19℃)128    CH3        4-CH3-Ph      nD1.582(21℃)129    CH3        4-NO2-Ph      m.p.88-90℃130    CH3        2，4-Cl2-Ph   nD1.59 6(24℃)131    CH3        3，5-Cl2-Ph   m.p.50-51℃132    CH3        2，6-F2-Ph    nD1.549(25℃)
表中所示化合物的糊状物的1HNMR(δ，CDCl3)数据如下：化合物53：
3.66(s；3H)，4.70(s；2H)，7.88(d；2H)，8.29(d；2H)化合物62：
3.70(s；3H)，3.86(s；3H)，4.65(s；2H)，6.92(d；2H)，
7.76(d；2H)化合物110：
3.94(s；3H)，4.50(s；2H)，5.11(s；2H)，
6.9-7.0(m；2H)，7.3-7.5(m；1H)化合物117：
3.91(s；3H)，4.02(s；2H)，7.5-7.7(m；3H)，
7.9-8.0(m；2H)
在如下的制剂实施例中，份数是重量份数。制剂实施例1
                            份数本发明的化合物                   50二甲苯                           40聚氧乙烯壬基苯基醚与烷基苯磺10酸的混合物
将上述成分均匀地混合并溶解形成乳剂。制剂实施例2
                           份数本发明的化合物                 0.5二甲苯                         0.8照明用煤油                     98.7
将上述成分均匀地混合并溶解形成润滑剂。制剂实施例3
                           份数本发明的化合物                 3粘土粉                         82硅藻土粉                       15
将上述成分均匀地混合并粉碎形成粉剂。制剂实施例4
                           份数本发明的化合物                 5皂土和粘土的混合物             90硬脂酸钙                       1
将上述成分均匀地混合，用适量的水揉合、制粒并干燥形成颗粒。制剂实施例5
                        份数本发明的化合物              20高岭土和高分散性合成硅酸的混75合物聚氧乙烯壬基苯基醚与烷基苯磺5酸钙的混合物
将上述成分均匀地混合并粉碎形成可湿的粉剂。制剂实施例6
                        份数本发明的化合物              1聚乙二醇400                 99
将上述成分均匀地混合并溶解形成涂抹溶液。制剂实施例7
                        份数本发明的化合物              2聚乙二醇400                 49聚乙二醇4000                49
将上述成分热混合，然后冷却形成软膏剂。制剂实施例8
                           份数本发明的化合物                 31，2-丙二醇                    5硬脂酸甘油酯                   5鲸蜡                           5肉豆蔻酸异丙酯                 10多乙氧基醚                     4
将以上成分的混合物加热，冷却。然后，搅拌的同时向其中加入68份水形成霜剂。试验实施例1  对水稻田的稻疫病(Pyricularia oryzae)作用的试验
将含本发明化合物作为活性成分的化学溶液(200ppm)充分施于罐中的水稻(5叶期)，并用空气干燥。随后，将含水稻的Pyricularia oryzae孢子的悬液喷在其中接种。
接种后，将盆置于-20℃温室中1天，温室中6天以让疾病完全出现。然后，测量每个叶子上的损伤数，计算与未处理组相比处理组的保护值。保护值按照下面的评价标准以保护效果来评价。结果列于表2。
评价标准：保护值(％)                         保护效果100-95                             A94-80                              B79-60                              C59-0                               - (空白)试验实施例2  对水稻种子的消毒作用试验
在25℃，将污染有稻恶苗赤霉的稻谷在浓度已调至1000ppm的试验试剂中浸泡24小时。将这样浸泡的稻谷轻轻地排水、播种并刺激发芽2天。用化学溶液处理三周后，测量仔苗的发病率，按照与试验实施例1相同的方法评价试验试剂的保护效果。结果列于表2。
         表2(抗病活性)No.           稻恶苗赤霉            Pyricularia oryzae1                                           C2               B4               B7               C10               A                           A13                                           B15                                           A19               A                           A20               C                           A23               C                           B24               B                           C26                                           B32                                           A33               B                           A34                                           A35               C                           A36               C                           A37               A                           A38               B                           A39               C40               C                           A42               B                           A43               A                           A
                  表2(续)No.           稻恶苗赤霉           Pyricularia oryzae45                B                         A52                                          A53                B54                B                         B55                C                         A57                A                         A60                C61                                          A62                A                         A63                A7172                B                         A75                                          A79                C                         A82                C                         A85                B                         A90                B                         A91                                          A93                                          A9495                B96                B                         A97                B                         A
                  表2(续)No.           稻恶苗赤霉              Pyricularia oryzae98               A99               B                            A100               B                            A102               A                            A103               A                            A104                                            A105               B                            A107               C                            A108               B                            A109               B                            A110               A                            A112               A113               A                            B114                                            C117               A                            A118               A                            A120               A125               B                            B128               B129               C                            A130               B                            A131                                            B132               A试验实施例3  对腐木真菌的杀微生物活性试验
将下列试验真菌在琼脂培养基中孵育。所得菌落通过直径4mm的软木孔与琼脂一起打孔，并用作接种源。将试验试剂加入到大麦提取物琼脂培养基中达50ppm的浓度，将混合物置于佩特里培养皿上。将上述制备的接种源放在其上，在28℃±2℃孵育。接种2至10天后，测量每个真菌菌落的直径，按照以下方程计算菌丝生长抑制的比率：菌丝生长抑制比率(％)＝(未处理组中的菌丝直径－试验组中的菌丝直径)÷未处理组的菌丝直径×100
菌丝生长抑制比率(％)以对真菌的杀微生物活性表达如下。结果列于表3。
评价标准：菌丝生长抑制比率(％)            杀微生物活性100-95                          A94-80                           B79-60                           C59-0                            - (空白)试验真菌：
担子菌纲
TYP：瘤盖干酪菌半知菌纲
TRV：绿色木霉子囊菌纲
CHG：球毛壳霉
             表3(杀菌活性)No.             TYP           TRV           CHG1               A             A             A2               A             A             A4               A             A             A7               A             A             A10               A             A             A1315               A             A             A19               A             A             B20               A             A             A23               A             A             C24               A             A             A26               A             B             A32               A             B             A33               A             A             A34               A             B             B35               A             A             A36               A             A             A37               A             A             A38               A             A             B39               A             A40               A             A             B42               A             A             A
               表3(续)No.             TYP           TRV           CHG43               A             A             B45               A             A             B52               A             A53               A             A             C54               A             A             A55               A             A             A57               A             A             A60               A             A             A61               A             A             A62               A             A             A63               A             A             A71                             B72               A75               A             A             A79               A             A             A82               A             A             A85               A             A             B90               A             A             A91               A             B             B93               A             B94               A             A             A95               A             A             A
             表3(续)No.           TYP         TRV           CHG96            A           A             A97            A           A             B98            A           A             A99            A           A             A100            A           A102            A           A             A103            A           A             A104            A           A             A105            A           A             A107            A           B             C108            A           A             C109            A           A             B110            A           A             A112            A           A             A113            A           A             A114            A           A             A117            A           A             A118            A           A             A120            A           A             A125            A           B             C126            A           A             A129            A           A             A
           表3(续)No.         TYP         TRV          CHG130          A           A            A131          A           B132          A           A            A试验实施例4  作为杀真菌剂(3-1)对白色假丝酵母的体外杀微生物活性的试验
将在37℃在Sabouraud葡糖琼脂(SGA)培养皿中孵育2小时的白色假丝酵母IFO 1270悬浮于无菌生理盐水中。用血细胞计数器测定所得悬液中的细胞数，并将细胞在生理盐水中的浓度调整至1×107细胞/毫升。以此方式，制备接种细胞溶液。将此接种细胞溶液(0.1毫升)及0.1毫升二甲基亚砜(DMSO)加入到9.8毫升Sabouraud葡糖肉汤(SGB)中，摇动的同时在37℃将混合物孵育48小时。孵育后，在波长650nm测量培养基的浊度，用下列表达式计算细胞生长抑制的比率。使用下列评价标准的该抑制比率表明了杀真菌活性。试验化合物的试验结果列于表4。细胞生长抑制比率＝(1－W/Y)×100(其中Y表示DMSO对照组的培养基浊度，W表示试验化合物的培养基浊度)
评价标准：细胞生长抑制比率(％)           杀真菌活性100-95                         A94-80                          B79-60                          C59-0                           - (空白)
 表4(杀真菌活性)No.           白色假丝酵母1                 A2                 A4                 A7                 A10                 A15                 A19                 A20                 A24                 A33                 A34                 A36                 A37                 A38                 A39                 A40                 A42                 A43                 A45                 A52                 A53                 A54                 A
 表4(杀真菌活性)No.                白色假丝酵母55                     A57                     A60                     A61                     A62                     A63                     A72                     A75                     A79                     A82                     A85                     A90                     A91                     A93                     A94                     A95                     A96                     A97                     A98                     A99                     A100                     A102                     A
             表4(杀真菌活性)
          No.               白色假丝酵母
          103                    A
          104                    A
          105                    A
          107                    A
          108                    A
          109                    A
          110                    A
          112                    A
          113                    A
          114                    C
          118                    A
          120                    A
          125                    A
          128                    A
          129                    A
          130                    A
          131                    A
          132                    A
本发明化合物具有优异的控制腐木真菌、植物疾病及人或动物真菌的作用，并可用作工业、农业及医药业杀真菌剂。

Claims (6)

1.式(I)的羟胺衍生物：
Figure A9611012600021
其中R表示
Figure A9611012600022
基团或
Figure A9611012600023
基团，其中R1和R2相同或不同并且每个代表C1-C12烷基；C2-C7链烯基；C2-C7炔基；C3-C7环烷基；C1-C7卤代烷基；C2-C7卤代炔基；C1-C7烷氧基-C1-C7烷基；苯氧基C1-C7-烷基；环上取代有一至五个取代基的苯氧基C1-C7-烷基，取代基可相同或不同并选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基；C1-C7烷基硫基-C1-C7烷基；C1-C7烷基磺酰基-C1-C7烷基；氨基-C1-C7烷基，它取代有一至二个相同或不同的取代基，取代基选自C1-C7烷基和C3-C7环烷基；苯基；环上取代有一至五个相同或不同的取代基的苯基，取代基选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基；苄基；环上取代有一至五个相同或不同的取代基的苄基，取代基选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基；萘基；环上取代有一至七个相同或不同的取代基的萘基，取代基选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基；苯乙基；环上取代有一至五个相同或不同的取代基的苯乙基，取代基选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基；肉桂基；环上取代有一至五个相同或不同的取代基的肉桂基，取代基选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基；吡啶基；环上取代有一至四个相同或不同的取代基的吡啶基，取代基选自卤原子、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基；呋喃基；取代有一至三个相同或不同的取代基的呋喃基，取代基选自卤原子、硝基、氰基、C1-C7烷基；噻吩基；取代有一至三个相同或不同的取代基的噻吩基，取代基选自卤原子、硝基、氰基和C1-C7烷基，且
X表示CO2、CO或SO2，
R3、R4、R5及R6相同或不同并且每个代表氢原子或C1-C7烷基，且
n表示0或整数1。
2.权利要求1所述的羟胺衍生物，其中R代表
Figure A9611012600041
基团，其中其中R1和R2相同或不同并且每个代表C1-C12烷基；C2-C7链烯基；C2-C7炔基；C3-C7环烷基；C1-C7卤代烷基；C2-C7卤代炔基；C1-C7烷氧基-C1-C7烷基；苯氧基C1-C7-烷基；环上取代有一至五个取代基的苯氧基C1-C7-烷基，取代基可相同或不同并选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一或二个相同或不同的C1-C7烷基的氨基；C1-C7烷基硫基-C1-C7烷基；C1-C7烷基磺酰基-C1-C7烷基；氨基-C1-C7烷基，它取代有一或二个相同或不同的取代基，取代基选自C1-C7烷基和C3-C7环烷基；苯基；环上取代有一至五个相同或不同的取代基的苯基，取代基选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一或二个相同或不同的C1-C7烷基的氨基；苄基；环上取代有一至五个相同或不同的取代基的苄基，取代基选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基；萘基；环上取代有一至七个相同或不同的取代基的萘基，取代基选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基；苯乙基；环上取代有一至五个相同或不同的取代基的苯乙基，取代基选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基；肉桂基；环上取代有一至五个相同或不同的取代基的肉桂基，取代基选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基；吡啶基；环上取代有一至四个相同或不同的取代基的吡啶基，取代基选自卤原子、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基、C1-C7卤代烷基磺酰基及取代有一至二个相同或不同的C1-C7烷基的氨基；呋喃基；取代有一至三个相同或不同的取代基的呋喃基，取代基选自卤原子、硝基、氰基、C1-C7烷基；噻吩基；取代有一至三个相同或不同的取代基的噻吩基，取代基选自卤原子、硝基、氰基和C1-C7烷基，且
X表示CO2、CO或SO2，
R3、R4、R5及R6相同或不同并且每个代表氢原子或C1-C7烷基，且
n表示0或整数1。
3.权利要求2的羟胺衍生物，其中R1为C1-C7烷基，且R2代表C1-C7烷基，苯基，环上取代有一至五个相同或不同的取代基的苯基，取代基选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷氧基羰基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基和C1-C7卤代烷基磺酰基，苄基，环上取代有一至五个相同或不同的取代基的苄基，取代基选自卤原子、硝基、氰基、C1-C7烷基、C1-C7卤代烷基、C1-C7烷氧基、C1-C7卤代烷氧基、C1-C7烷基硫基、C1-C7卤代烷基硫基、C1-C7烷基磺酰基和C1-C7卤代烷基磺酰基，
X表示CO2或CO，
R3、R4、R5及R6相同或不同并且每个代表氢原子或C1-C7烷基，且
n表示0或整数1。
4.含有权利要求1、2或3中所述羟胺衍生物作为活性成分的工业杀真菌剂。
5.含有权利要求1、2或3中所述羟胺衍生物作为活性成分的农业和园艺杀真菌剂。
6.含有权利要求1、2或3中所述羟胺衍生物作为活性成分的医药业杀真菌剂。
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