CN1133590A - 丁烯醇-三唑基衍生物,其制备及其作为杀微生物剂的用途 - Google Patents
丁烯醇-三唑基衍生物,其制备及其作为杀微生物剂的用途 Download PDFInfo
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- CN1133590A CN1133590A CN94193834.4A CN94193834A CN1133590A CN 1133590 A CN1133590 A CN 1133590A CN 94193834 A CN94193834 A CN 94193834A CN 1133590 A CN1133590 A CN 1133590A
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- carbon atom
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- alkyl
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Abstract
式(I)的新的丁烯醇-三唑基衍生物及其酸加成盐和金属盐络合物,其中X为氢、卤素、具有1至4个碳原子的烷基或具有1至4个碳原子的烷氧基,Z为卤素、具有1至4个碳原子的烷基,具有1至4个碳原子和1至5个卤原子的卤代烷基、具有1至4个碳原子的烷氧基、具有1至4个碳原子和1至5个卤原子的卤代烷氧基、硝基或可任选被相同或不同的卤原子单取代至三取代的苯基;和m为0、1、2或3的数字,生产上述新物质的方法及其在植物和材料保护中用作杀微生物剂的用途。本文还公开了新的式(Ⅱ)丁烯醇衍生物、新的式(Ⅲ)环氧乙烷和新的式(X)酮,及其制造方法和其用作合成式(I)化合物中间体的用途。
Description
本发明涉及新的羟基乙基-氮杂茂环基(azolyl)衍生物,其制备方法,及其在植物保护和材料保护中用作杀微生物剂的用途。
已知大量的羟基乙基-氮杂茂环基衍生物具有杀真菌的性质(参见:EP-OS 0 251 086,WO 89-05581和WO 91-12000)。例如,可用2-(2-氯苯基)-3-(2,4-二氯苯基)-3-羟基-4-(1,2,4-三唑-1-基)-丁-1-烯和2-(2-氟苯基)-3-(4-氯苯基)-3-羟基-4-(1,2,4-三唑-1-基)-丁-1-烯杀灭真菌。可是,在许多情况下当以低剂量使用时,上述物质的活性不能满足需要。
子的烷氧基,Z 代表卤素、具有1至4个碳原子的烷基、具有1至4个碳原子和
1至5个卤原子的卤代烷基、具有1至4个碳原子的烷氧基、具
有1至4个碳原子和1至5个卤原子的卤代烷氧基、硝基、或被
相同或不同的卤原子可任选单取代至三取代的苯基,和m 代表0、1、2或3的数字。
根据本发明的物质包含一个不对称取代的碳原子。因此可获得旋光异构体形式的上述物质。本发明涉及单独的异构体及其混合物。
X、Z和m具有上述定义和
Hal代表氯或溴,或b)式(III)的环氧乙烷类化合物,
其中
最后,已发现式(I)的新的羟基乙基-氮杂茂环基衍生物及其酸加成盐和金属盐络合物具有极好的杀微生物的活性,并可在植物保护和材料保护中使用。
令人惊奇的是,根据本发明的物质与相同作用目的和结构非常接近的已知化合物相比,在植物保护和材料保护中都具有较好的杀微生物活性。因此,根据本发明的物质例如与2-(2-氯苯基)-3-(2,4-二氯苯基)-3-羟基-4-(1,2,4-三唑-1-基)-丁-1-烯和2-(2-氟苯基)-3-(4-氯苯基)-3-羟基-4-(1,2,4-三唑-1-基)-丁-1-烯相比,具有优越的杀真菌性质。
式(I)提供了根据本发明的羟基乙基-氮杂茂环基衍生物的总的定义。X 优选代表氢、氟、氯、甲基、乙基、正丙基、异丙基、甲氧基和
乙氧基。Z 优选代表氟、氯、溴、甲基、乙基、正丙基、异丙基、正丁基、
仲丁基、异丁基、叔丁基、三氯甲基、三氟甲基、二氟甲基、甲
氧基、乙氧基、三氟甲氧基、二氟甲氧基、硝基,或代表可被相
同或不同的氟和/或氯任选单取代或二取代的苯基。m 优选代表0、1、2或3的数字,如果m代表2或3,则Z可以
代表相同或不同的基团。
根据本发明优选的物质为酸与式(I)羟基乙基-氮杂茂环基衍生物的加成产物,其中X、Z和m具有上述给出的优选定义。
可进行加成反应的酸优选包括氢卤酸,如,氢氯酸和氢溴酸,特别是氢氯酸,以及磷酸、硝酸、硫酸、单-和二官能基羧酸和羟基羧酸,例如,乙酸、马来酸、琥珀酸、富马酸、酒石酸、柠檬酸、水杨酸、山梨酸和乳酸,以及磺酸,例如:对甲苯磺酸、1,5-萘二磺酸或樟脑磺酸、糖精和硫代糖精。
根据本发明其它优选的化合物是元素周期表中II-IV主族和I和II和IV至VIII副族金属盐与其中X、Z和m为上述给出的优选定义的上述式(I)的羟基乙基氮杂茂环基衍生物的加成产物。
在本文中特别优选的是铜、锌、锰、镁、锡、铁和镍盐。上述盐的适合阴离子从能生成生理上可接受的加成产物的那些酸中得到。在本文中,特别优选的上述类型的酸为:氢卤酸例如,氢氯酸和氢溴酸,以及磷酸、硝酸和硫酸。
可述及的式(I)羟基乙基-氮杂茂环基衍生物类物质的实例列示于下表中。
式(II)提供了在本发明方法(a)中用作起始物所需的丁烯醇衍生物的总的定义。在该式中X、Z和m优选为早已述及的与本发明式(I)物质的说明有关的上述定义,其为上述基团或上述指数的优选定义。Hal代表氯或溴。
在按照上述方法制备式(II)丁烯醇-衍生物时作为起始物质所需的式(V)的环丙基酮类化合物是已知的(参见EP-OS 0 297 345)。
在上述式(II)丁烯醇衍生物的制备方法中用作反应物所需的式(VI)有机金属化合物是已知的或原则上可通过已知方法制备的(参见:J.Org.Chem.41(1976),3725)。例如,上述物质的制备是通过式(VII)的苯乙烯衍生物
其中Z和m具有上述给出的定义,与溴,在如四氯化碳、氯仿或二氯甲烷的稀释剂存在下,在0℃至30℃的温度下反应,使所得的式(VIII)的溴化物其中Z和m具有上述给出的定义在如甲苯、四氢呋喃或二噁烷的稀释剂存在下,和在如二氮杂二环壬烯(DBN)、二氮杂二环十一碳烯(DBU)或氢氧化钾的碱存在下,在相转移催化剂存在下,在0℃至130℃的温度下反应,且使所得的式(IX)的溴苯乙烯衍生物其中Z和m具有上述给出的定义与镁屑在如乙醚或四氢呋喃的稀释剂存在下,在0℃至70℃的温度之间进行反应。
在上述式(II)丁烯醇衍生物的制备方法中适合的稀释剂为上述类型反应中经常使用的各种惰性有机溶剂。可优选使用的为醚类,如乙醚、四氢呋喃和二噁烷。
在进行上述式(II)丁烯醇衍生物的制备方法时,反应温度可在一定的范围内变化。通常,反应在-80℃至+60℃的温度下进行。
上述式(II)丁烯醇衍生物的制备方法通常在大气压力下进行。可是,也可以在提高或降低的压力下进行上述方法。
当进行上述式(II)丁烯醇衍生物的制备方法时,对每1mol的式(V)的环丙基酮通常使用1至1.2mol的式(VI)的有机金属化合物,且在使用前立即制备上述有机金属化合物是方便的并可在其原位反应。通过常规方法进行加工处理。通常,方法为首先酸化混合物接着加入水,然后将有机相分离、冲洗、干燥并浓缩。
在根据本发明的方法变体(b)中作为起始原料需要的环氧乙烷类化合物由式(III)一般性定义,在上式中,X、Z和m优选为上述定义。该定义为与根据本发明已述及的通式(I)物质的描述相联系的优选的上述基团或系数。
其中
通过上述方法(c)制备式(III)的环氧乙烷类化合物时适合的碱为一般适合上述反应的所有的无机和有机碱,可优选使用下述的碱:碱金属碳酸盐,如碳酸钠和碳酸钾,以及碱金属氢氧化物如氢氧化钠和氢氧化钾。还有碱金属醇化物,如甲醇钠和甲醇钾、乙醇钠、乙醇钾和叔丁醇钾,和低级叔烷基胺、环烷基胺和芳烷基胺,特别如三乙胺。
通过上述方法(c)制备式(III)的环氧乙烷类化合物时适合的稀释剂为所有的常规惰性有机溶剂。可优选使用下述溶剂:腈类,如乙腈,和芳香烃类,如苯、甲苯和二氯苯,还有甲酰胺,如二甲基甲酰胺以及强极性溶剂,如二甲基亚砜和六甲基磷酰三胺。
当通过上述方法(c)制备式(III)的环氧乙烷类化合物时,反应温度可在一定的范围内变化。通常,上述方法在0℃至100℃,优选20℃至60℃的温度下进行。
通常在常压下进行制备式(III)环氧乙烷类化合物的上述方法(c)。可是,还可在提高或降低的压力下进行上述方法。
当进行制备式(III)的环氧乙烷类化合物的上述方法(c)时,对每1mol的式(II)的丁烯醇衍生物通常使用1至3mol的碱。通过常规的方法进行加工处理。
式(X)提供了进行制备式(III)环氧乙烷类化合物的上述方法(d)时用作起始物的酮的总的定义。在上式中,X、Z和m优选为上述定义,该定义为与根据本发明已述及的式(I)物质的描述相联系的优选的上述基团或系数。
式(X)的酮迄今是未知的,它们可通过式(XII)的苄基酮其中X、Z和m为上述定义或者α)与式(XIII)双-(二甲基氨基)-甲烷
(CH3)2N-CH2-N(CH3)2(XIII)在乙酸酐或冰醋酸存在下反应,或β)在催化剂存在下和在稀释剂存在下与多聚甲醛或福尔马林反应而制备。
式(XII)提供了通过上述方法制备式(X)的酮时用作起始物的苄基酮的总的定义。在上式中X、Z和m优选为上述定义。该定义为与根据本发明已述及的式(I)物质的描述相联系的优选的上述基团或系数。
式(XII)的苄基酮是已公知的或可通过一般的已知方法制备的(参见.EP-OS 0 461 483和EP-OS 0 461 502)。
进行上述方法(d)时所需的反应物即式(XIII)的双-(二甲基氨基)-甲烷,或多聚甲醛或福尔马林(甲醛含量为37%的甲醛水溶液)是已知的。
当进行制备式(X)的酮的上述方法变体(α)时,反应温度可在很大的范围内变化。通常,上述方法在20℃至120C,优选在30℃至110C的温度范围下进行。
当进行上述制备式(X)的酮的方法变体(α)以及(β)时通常在常压下进行。可是,上述方法也可在提高或降低的压力下进行。
当进行制备式(X)的酮的上述方法变体(α)时,对每1mol的式(XII)的苄基酮通常使用3至4mol的式(XIII)的双-(二甲基氨基)-甲烷。通过常规方法进行加工处理。
进行制备式(X)酮的上述方法变体(β)时,适合的催化剂为用于上述反应的常规的所有反应促进剂。可优选使用碱金属氢氧化物,如氢氧化钠或氢氧化钾。
进行制备式(X)酮的上述方法变体(β)的稀释剂为适合上述反应的常规的各种惰性、有机溶剂。可优选使用醇类,如甲醇或乙醇。
当进行制备式(X)酮的上述方法变体(β)时,反应温度可在一定的范围内变化。通常,上述方法可在10℃至40℃,优选在室温下进行。
当进行制备式(X)酮的上述方法变体(β)时,对每1mol的式(XII)的苄基酮,通常使用1.5至2.5当量的多聚甲醛或福尔马林和等当量的催化剂。采用常规的方法进行加工处理。
在制备式(III)环氧乙烷类化合物的上述方法(d)中用作反应物的式(XI)亚甲基化二甲基锍是已知的(参见Heterocycles 8 397(1977))。在上述反应中,应使用新制备的式(XI)化合物,其制备例如是在强碱存在下,在稀释剂存在下从例如卤化三甲基锍或三甲基锍甲基硫酸盐就地制备,强碱如氢化钠、氨基钠、甲醇钠、叔丁醇钾或氢氧化钾,稀释剂如叔丁醇或二甲基亚砜。
进行制备式(III)的环氧乙烷类化合物的上述方法(d)时适合的稀释剂是惰性有机溶剂,可优选使用下述稀释剂:醇类、如叔丁醇、醚类,如四氢呋喃或二噁烷,以及脂族和芳族烃类,如苯、甲苯或二甲苯,和强极性溶剂,如二甲基亚砜。
当进行制备式(III)的环氧乙烷类化合物的上述方法(d)时,反应温度可在相当宽的范围内变化。通常在0℃至100℃,优选10℃至60℃的温度下进行上述方法。
当进行制备式(III)的环氧乙烷类化合物的上述方法(d)时,对每1mol式(X)的酮,通常使用1至3mol的式(XI)的亚甲基化二甲基锍。通过常规方法进行加工处理。
进行本发明方法的适合的酸结合剂是各种常用的无机或有机碱。可优选使用下述碱:碱金属碳酸盐,如碳酸钠和碳酸钾,以及碱金属氢氧化物,如氢氧化钠和氢氧化钾,还有碱金属醇化物,如甲醇钠和甲醇钾、乙醇钠、乙醇钾和叔丁醇钾,和低级叔烷基胺,环烷基胺和芳烷基胺,特别如三乙胺。
适合于进行根据本发明方法的稀释剂为各种常规的惰性有机溶剂。可优选使用下述溶剂:腈类,如乙腈,以及芳香烃类,如苯、甲苯和二氯苯。还有甲酰胺类,如二甲基甲酰胺,和强极性溶剂,如二甲基亚砜和六甲基磷酰三胺。
当进行根据本发明的方法时,反应温度可在相当宽的范围内变化。通常,本方法在0℃至130℃,优选40℃至120℃的温度下进行。
而且,本发明的方法通常在常压下进行。可是,还可以在提高或降低的压力下进行本方法。
当进行本发明的方法时,对每1mol的式(II)的丁烯醇衍生物或式(III)的环氧乙烷类化合物通常使用1至4mol的式(IV)1,2,4-三唑和0.3至3mol的酸结合剂。通过常规方法进行加工处理。通常的方法是:浓缩反应混合物,将所剩下的残留物用与水不明显混溶的有机溶剂吸收,并用水冲洗混合物,干燥并浓缩。如果必要,将剩余的产物直接进行其它的提纯方法。
根据本发明的式(I)羟乙基-氮杂茂环基衍生物可被转化成其酸加成盐或金属盐络合物。
适合制备式(I)化合物的酸加成盐的酸优选为已述及的与本发明酸加成盐的描述相联系的优选的酸。
可以简单的方式通过常规的形成盐的方法制备式(I)化合物的酸加成盐,例如将式(I)化合物溶于适合的惰性溶剂中,并加入如盐酸的酸、并将其按照已知方法例如过滤分离,且如果必要,通过用惰性有机溶剂冲洗而纯化。
非常适合制备式(I)化合物的金属盐络合物的盐优选为已经描述过的与本发明优选金属盐的金属盐络合物相联系的那些金属盐。
可以简单的方式通过常规的方法制备式(I)化合物的金属盐络合物,例如通过将金属盐溶于乙醇的醇,并向溶液中加入式(I)化合物。可通过已知的方法分离金属盐络合物。例如通过过滤的方法,且如果必要,可将其通过重结晶的方法提纯。
本发明的活性化合物具有很强的杀微生物活性并可在植物保护和材料保护中消灭如真菌和细菌的有害微生物。
在植物保护中可使用本杀真菌剂消灭根肿病菌纲、卵菌纲、壶菌纲、接合菌亚纲、子囊菌纲、担子菌纲和半知菌纲的真菌。
以下以非限定的方式例示了上述总称下的一些真菌和细菌病害的致病微生物:黄杆菌属:如黄杆菌;假单胞菌属:如黄瓜角斑病极主杆菌;欧代植病杆菌属:梨火疫病欧代杆菌;腐霉属:如甘薯斑腐病;疫霉属:如马铃薯晚疫病;假霜霉属:如葎草假霜霉或生姜腐败病;单轴霉属:如葡萄霜霉病;霜霉菌属:如豌豆霜霉或大白菜霜霉病、白粉菌属:如葫芦白粉病;球壳霉属:如黄瓜白粉病;足球霉属:如苹果白粉病;黑星菌属:如苹果黑星病;Pyrenophora属:如大麦网斑病或大麦条纹病(分生孢子型:如眼斑病,同物异名:大麦网斑霉);旋孢霉属:如稻胡麻斑病(分生孢子型:眼斑点,同物异名:长蠕孢菌);单孢锈菌属:如菜豆锈病;
双孢锈菌属:如小麦叶锈病;腥黑粉菌属:如小麦网星黑穗病;黑粉菌属:如Ustilago nuda或燕麦散黑穗病;薄膜霉属:如稻纹枯病;梨孢霉属:如稻瘟病;镰刀霉属:如禾杆镰孢菌;葡萄孢属:如灰葡萄孢;壳针孢霉属:如小麦颖枯病;细球壳菌属:如小麦白叶斑病;尾孢霉属:如小豆褐斑病;交链孢属:如甘兰黑斑病;葡萄假尾孢霉属:如Pseudocercosporella herpotrichoides。
由于植物对防治植物病害所需浓度的活性化合物的良好的耐受性,使得可用其处理植物的地上部分,植物的繁殖根茎和种子,以及土壤。
根据本发明的活性化合物特别适合防治水稻上的稻瘟病和稻纹枯病和防治谷物病害,如小麦白叶斑病,稻胡麻斑病,大麦网斑病、葡萄假尾孢霉(Pseudocercosporella herpotrichoides)、白粉菌属和镰刀霉属的病害。而且,本发明的化合物具有非常好的和广谱的离体活性。
在材料保护上,可以应用本发明的化合物保护工业材料免受有害微生物的攻击和破坏。
可将本文中的工业材料理解为采用工业技术制备的无生命的材料,用本发明活性化合物保护的免受微生物改变或损坏的工业材料的实例为胶、胶料、纸和纸板、纺织品、皮革、木材、油漆和塑料制品、冷却润滑剂或可被微生物进攻或分解的其它材料。微生物繁殖对其可产生有害影响的工厂生产设备的零件,例如冷却水管道也包括在要被保护的材料的范围内。可优选述及的在本发明范围内的工业材料为胶、胶料、纸和纸板、皮革、木材、油漆、冷却润滑剂和热交换液,更特别述及的是木材。
可引起工业材料降解或变化的微生物的实例为细菌、真菌、酵母、藻类和粘液细菌。本发明的活性化合物优选对真菌,特别是霉菌,引起木材脱色和木材损害的真菌(担子菌)和对粘液细菌和藻类优选具有活性。
可述及的实例为下述属的微生物:交链孢:如细交链孢;麦霉:如黑麦霉;毛壳霉:如球毛壳霉;粉孢革菌:如湿腐粉孢革;香菇属:如豹斑菌;青霉:如灰绿青霉;多孔菌,如变色多孔菌;金黄担子菌:如暗金黄担子菌;Sclerophoma,如Sclerophoma pityophila;木霉:如绿木霉;埃希氏杆菌:大肠杆菌;假单胞菌:如铜绿色极毛杆菌;葡萄球菌:金黄色葡萄球菌。
本发明活性化合物可被转化成为常规的制剂,如液剂、乳剂、悬浮剂、粉剂、泡沫剂、糊剂、颗粒剂、气雾剂,在聚合物中的微细胶囊和种子包衣组合物,以及超低容量制剂。
这些制剂是以已知方法生产的,例如,通过将活性成分与填充剂,即液体溶剂,加压下为液体的气体,和/或固体载体混合而生产,制剂中可任选使用表面活性剂,即乳化剂和/或分散剂,和/或成泡剂。在使用水作为填充剂的情况下,例如,也可使用有机溶剂作为助溶剂。适合的液体溶剂主要有:芳香烃类,如二甲苯、甲苯或烷基萘,氯代芳烃类或氯代脂肪烃类,如氯苯,二氯乙烯或二氯甲烷,脂肪烃类,如环己烷或烷属烃,例如矿物油馏分,醇类,如丁醇或乙二醇及其醚和酯类,酮类,如丙酮,甲基乙基酮,甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺和二甲基亚砜,以及水;液化气体填充剂或载体意为在常温和常压下是气体的液体,例如气雾推进剂,如丁烷,丙烷,氮气和二氧化碳;适合的固体载体有:例如,天然矿物粉末,如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱土或硅藻土,和合成矿物粉末,如高分散硅酸,氧化铝和硅酸盐;适合颗粒剂的固体载体有:例如,粉碎和分级的天然岩石,如方解石、大理石、浮石、海泡石和白云石,以及无机的合成颗粒和有机粉末,和有机材料的颗粒如锯末,坚果壳,玉米穗茎和烟草茎;适合的乳化剂和/或成泡剂有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯,聚氧乙烯脂肪醇醚,例如烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白水解产物。适合的分散剂有:例如木质素亚硫酸废液和甲基纤维素。
在制剂中还可使用粘合剂如羧甲基纤维素和粉末、颗粒或胶乳状天然和合成聚合物,如阿拉伯树胶,聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂如脑磷脂和卵磷脂,和合成磷脂。其它的添加剂可以是矿物油和植物油。
可能使用的着色剂如无机颜料,例如氧化铁,氧化钛和普鲁士兰,和有机染料,如茜素染料,偶氮染料和金属酞菁染料,和痕量营养物例如铁、锰、硼、铜、钴、钼和锌盐。
制剂中通常含有按重量计0.1%-95%,优选按重量计0.5%-90%的活性化合物。
在用于植物保护时,根据本发明的活性化合物可以其本身或以与已知杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀虫剂的混合物的制剂形式使用,例如这样可以扩大作用谱或防止抗性的形成。在许多情况下可以观察到增效作用,这意味着组合物的活性大于单独成分活性的总和。
适用于混合物的各种成分的实例为下述的物质。杀真菌剂:
2-氨基丁烷2-苯胺基-4-甲基-6-环丙基-嘧啶;2′,6′-二溴-2-甲基-4′-三氟甲氧基-4′-三氟甲基-1,3-噻唑-5-N-甲酰苯胺;2,6-二氯-N-(4-三氟甲基苄基)苯甲酰胺;(E)-2-甲氧基亚氨基-N-甲基-2-(2-苯氧苯基)-乙酰胺;8-羟基喹啉硫酸盐;(E)-2-{2-[6-(2-氰基苯氧基)-嘧啶-4-基氧]-苯基}-3-甲氧丙烯酸甲基酯;(E)-甲氧基亚氨基[α-(对甲苯氧基)-对甲苯基]乙酸甲酯;2-苯基苯酚(OPP),艾敌吗啉,Ampropylfos,敌菌灵,戊环唑;
苯霜灵,麦锈灵,苯菌灵,Binapacryl,联苯酚,双苯三唑醇,灭瘟素,乙嘧酚磺酸酯,糠菌唑,粉病定;
多硫化钙,敌菌丹,克菌丹,多菌灵,萎锈灵,灭螨猛,地茂散,氯化苦,百菌清,乙菌剂,硫杂灵,霜脲氨,环唑醇,酯菌氨;
双氯酚,苄氯三唑醇,苯氟磺胺,达菌清,氯硝胺,乙霉威,恶醚唑、甲菌定,烯酰吗啉,烯唑醇,敌螨普,二苯酚,Dipyrithion,灭菌磷,二嗪农,多果定,敌菌酮;
克瘟散,Epoxyconazole,乙菌克,氯唑灵;
异嘧菌醇,Fenbuconazole,呋菌胺,种衣醇,拌种咯,苯锈啶,丁苯吗啉,薯瘟锡,毒菌锡,福美铁,嘧菌腙,氟啶胺,Fludioxonil,氟菌安,Fluquinconazole,氟硅唑,磺菌胺、氟酰胺,粉唑醇,灭菌丹,乙磷铝,四氯苯酞,麦穗宁,呋氨丙灵,拌种胺;
双胍盐;
氯苯嘧啶醇,己唑醇,土消菌;
烯菌灵,酰胺唑,双胍辛醋酸盐,Iprobenfos(IBP),异丙定,富士一号;
春雷霉素,铜制备物:如氢氧化铜,环烷酸酮,氯氧化铜,硫酸铜,氧化铜,8-羟基喹啉铜和波尔多混合物:
锰铜混剂,代森锰锌,代森锰,嘧菌胺,灭锈胺,瑞毒霉,Metconazol,磺菌威,甲呋菌胺,代森联,Metsulfovax,氰菌唑;
福美镍,异丙消,环菌灵;
甲呋酰胺、噁霜灵,Oxamocarb,氧化萎锈灵;
稻瘟酯,戊菌唑,戊隆醇,Phosdiphen,多马霉素,粉病灵,多氧霉素,噻菌灵,并氯灵,杀菌利,百维灵,丙环唑,甲基代森锌,定菌磷,啶斑肟,Pyrimethanil,毛醌素,五氯硝基苯(PCNB);
硫和硫制备物;
戊唑醇,白叶减,四氯硝基苯,氟醚唑,涕必灵,噻菌腈,甲基托布津,福美双,甲基立桔磷,对甲抑菌灵,唑菌酮,唑菌醇,唑菌嗪,杨菌胺,三环唑,克啉菌,氟菌唑,嗪氨灵;
Triticonazol;
有效霉素,烯菌酮;
代森锌,福美锌。杀细菌剂:
溴硝丙二醇、双氯酚、氯定、福美镍、春雷霉素、Octhilinon、呋喃甲酸、羟基喹啉、噻菌灵、链霉素、白叶减、硫酸铜和其它铜制备物。杀虫剂/杀螨剂/杀线虫剂:
齐墩螨素(Abamectin),AC 303 630,乙酰甲胺磷,氟硝菊酯,棉铃威,涕灭威,甲体氯氰菊酯,虫螨脒,齐墩螨素(Avermectin),AZ 60541,Azadirachtin,谷硫磷,乙基谷硫磷,唑环锡;
苏云菌杆菌,噁虫威,丙硫克百威,杀虫磺,氟氯氰菊酯,氟氯菊酯,丁苯威,溴硫磷,Bromophos A,全杀威,噻嗪酮,丁叉威,达螨酮;
硫线磷,西维因,呋喃丹,三硫磷,丁硫克百威,杀螟丹,CGA157 419,CGA 184699,Chloethocarb,Chlorethoxyfos,Chlortenvinph,定虫隆(Chlorfluazuron),氯甲硫磷,毒死蜱,甲基毒死蜱、顺-苄呋菊酯,Clocythrin,四螨嗪,杀螟腈,乙腈菊酯,β-氟氯氰菊酯,三氟氯氰菊酯,三环锡,氯氰菊酯,灭蝇胺;
溴氰菊酯,甲基内吸磷,甲基内吸磷S赶式异构体,内吸磷,杀螨隆,二嗪农,除线磷,敌敌畏,Dicliphos,百治磷,乙硫磷,氟脲杀,乐果,甲基毒虫畏,敌杀磷,乙拌磷,克瘟散,Emamectin,高氰戊菊酯,苯虫威,乙硫磷,醚菊酯(Ethofenprox),Ethoprophis,Etofenprox,氯嘧啶磷;
克线磷,喹螨醚,杀螨锡,杀螟松,Fenobucarb,苯硫威,双氧威,分扑菊酯,Fenpyrad,唑螨酯,倍硫磷,氰戊菊酯,Fipronil,氟啶胺,氟螨脲,氟氰戊菊酯,氟虫脲,Flufenprox,氟胺氰菊酯,地虫磷,安果,噻唑硫磷,Fubfenprox,呋线威;
六六六,庚虫磷,氟铃脲,噻螨酮;
咪蚜胺,Iprobenfos,异唑磷,丙胺磷,异丙威,异噁唑磷,齐墩螨素,(Ivemectin),入-三氟氯氰菊酯,Lufenuron;
马拉硫磷,灭蚜磷,Mervinphos,甲丙硫磷,多聚乙醛,虫螨畏,甲胺磷,杀扑磷,灭虫威,灭多威,Metolcarb,Milbemectin,久效磷,Moxidectin;
二溴磷,NC 184,NI 25,Nitenpyram,
氧化乐果,甲叉丙威,砜吸磷,Oxydeprofos,对硫磷,甲基对硫磷,氯菊酯,稻丰散,甲拌磷,伏杀磷,亚胺硫磷,磷胺,辛硫磷,抗蚜威,虫螨磷,乙基虫螨磷,溴丙磷,锰杀威,丙虫磷,残杀威,丙硫磷,发果,Pymetrozin,吡唑硫磷,哒嗪硫磷,反灭菊酯,除虫菊,哒嗪酮,Pyrimidifen,蚊蝇醚,喹硫磷;
RH 5992;
杀抗松,克线丹,Silafuofen,治螟磷,乙丙硫磷;
Tebufenozide,Tebufenpyrad,Tebupirimphos,伏虫隆,七氟菊酯,双硫磷,叔丁威,特丁磷,杀虫威,Thiafenox,硫双灭多威,特氨叉威,甲基乙拌磷,治线磷,苏云菌杆菌,四溴菊酯,Triarathen,三唑磷,Triazuron,敌百虫,Triflumuron,三叉威;
蚜灭多,二甲威,Xylylcarb,Zetamethrin。
与其它已知活性化合物,如除草剂或肥料和植物生长调节剂的混合物也是存在的。
可以活性化合物本身或以其制剂形式或从制剂制备的应用形式如现用溶液、悬浮液、可湿性粉剂、糊剂、可溶粉剂、粉剂和颗粒剂使用本活性化合物。可以常规方法,例如采用泼浇、喷雾、弥雾、分散、喷粉、泡沫、刷涂等方法使用上述制剂,还可能通过超低容量方法或将活性化合物的制剂或活性化合物本身注入土壤中的方式使用活性化合物。也可用来处理植物的种子。
在处理植物体时,在应用形式中的活性化合物的浓度可在相当宽的范围内变化,通常其为1至0.0001%(重量),优选0.5至0.001%(重量)。
在处理种子时,对每公斤种子通常需要活性化合物的量为0.001至50g,优选0.01至10g。
在土壤处理时,在作用位点需要的活性化合物的浓度为0.00001至0.1%(重量),优选0.0001至0.02%(重量)。
用于工业材料保护的试剂通常含有1至95%,优选10至75%的活性化合物。
本发明活性化合物的使用浓度根据被防治的微生物的种类和出现以及要被保护材料的组成而变化。可通过-系列试验确定最佳施用剂量。通常,以被保护的材料为准计使用浓度在0.001至5%(重量),优选0.05至1.0%(重量)。
在材料保护中可使用的根据本发明的活性化合物,或由其制备的组合物,浓缩物或一般制剂的活性和作用谱,在适合的情况下,可通过加入其它杀微生物活性化合物、杀真菌剂、杀细菌剂、除草剂、杀虫剂和其它能够扩宽作用谱或获得特殊效果,如对昆虫有保护作用的活性化合物而增加。与本发明化合物相比,上述组合物具有较宽的作用谱。
在许多情况下,其结果是增效作用,即组合物的活性超过单独成分的活性。在组合物中特别优选的成分是下述化合物:亚磺酰类:如抑菌灵(Euparen),对甲抑菌灵(Methyleuparen),灭菌丹、Fluorfolpet;苯并咪唑类:如多菌灵(MBC)、苯菌灵、麦穗宁、涕必灵及其盐;硫氰酸酯类:如硫氰基甲硫基苯并噻唑(清菌噻唑)、亚甲基双硫氰酸酯(巯苯噻唑);季铵盐化合物,如氯化苄基二甲基十四碳烷基铵、氯化苄基-二甲基十二碳烷基铵,氯化十二烷基-二甲基-铵;吗啉衍生物,如C11-C14-4-烷基-2,6-二甲基吗啉同系物(克啉菌)、(±)-顺-4-[叔-丁基苯基)-2-甲基丙基]-2,6-二甲基吗啉(丁苯吗啉)、Falimorph;苯酚类,如邻苯基苯酚、三溴苯酚、四氯苯酚、五氯苯酚、3-甲基-4-氯苯酚、双氯酚、氯酚或其盐类;氮杂茂环类,如唑菌酮、唑菌醇、双苯三唑醇、戊唑醇、丙环唑、戊环唑、己唑醇、丙氯灵、环唑醇、1-(2-氯苯基)-2-(1-氯环丙基)-3-(1,2,4-三唑基-1-基)-丙-2-醇或1-(2-氯苯基)-2-(1,2,4-三唑-1-基-甲基)-3,3-二甲基-丁-2-醇;碘代炔丙基衍生物,如碘炔丙基-丁基氨基甲酸酯(IPBC)、碘炔丙基-氯苯基缩甲醛、碘炔丙基-苯基氨基甲酸酯、碘炔丙基-己基氨基甲酸酯、碘炔丙基-环己基氨基甲酸酯和碘炔丙基氧乙基苯基氨基甲酸酯;碘衍生物:如二碘甲基-对芳基砜;例如二碘甲基-对甲苯基砜;溴衍生物:如溴硝丙二醇;异噻唑啉类:如N-甲基异噻唑啉-3-酮、5-氯-N-甲基异噻唑啉-3-酮、4,5-二氯-N-辛基异噻唑啉-3-酮、N-辛基异噻唑啉-3-酮(Octilinone);苯并异噻唑啉酮、环戊烯基异噻唑啉;吡啶类,如1-羟基-2-吡啶硫酮(及其钠、铁、锰和锌盐)、四氯-4-甲基磺酰基吡啶;金属皂类,如环烷酸、辛酸、2-乙基己酸、油酸、磷酸、苯甲酸的锡、铜和锌盐,和氧化物类,如丁蜗锡、Cu2O、CuO、ZnO;有机锡化合物,如环烷酸三丁基锡和氧化三丁基锡;二烷基二硫代氨基甲酸酯:如二烷基二硫代氨基甲酸钠盐和锌盐、四甲基秋兰姆二硫化物(福美双);腈类:如2,4,5,6-四氯异邻苯二甲腈(百菌清)和具有一个活化的卤素基团的杀微生物剂如Cl-Ac、氯乙酸、Tectamer、溴硝丙二醇、Bromidox;苯并噻唑类:如2-巯基苯并噻唑、参见上述的棉隆;喹啉类:如8-羟基喹啉;释放甲醛的化合物:如苄基醇单(聚)半缩醛、噁唑啉类,六氢-s-三嗪类、N-甲醇基氯乙酰胺;三-N-(环己基二氮烯鎓二氧)-铝、N-(环己基二氮烯鎓二氧)-三丁基锡或钾盐、双-(N-环己基)二嗪鎓-(二氧-铜或铝)。优选加入的杀虫剂为:磷酸酯类:如乙基谷硫磷、谷硫磷、1-(4-氯苯基)-4-(O-乙基,S-丙基)磷酰基氧吡啶(吡唑硫磷)、毒死蜱、蝇毒磷、内吸磷、甲基内吸磷、二嗪农、敌敌畏、乐果、醚菊酯、氯嘧啶磷、杀螟松、倍硫磷、庚虫磷、对硫磷、甲基对硫磷、伏杀磷、辛硫磷、乙基虫螨磷、虫螨磷、溴丙磷、丙硫磷、乙丙硫磷、三唑磷和敌百虫。氨基甲酸酯类:如涕灭威、噁虫威、丁苯威(2-(1-甲基丙基)苯基甲基氨基甲酸酯)、丁叉威、氧丁叉威、西维固、呋喃丹、丁硫克百威、Cloethocarb、异丙威、灭多威、甲叉丙威、抗蚜威、猛杀威、残杀威和硫双灭多威。合成除虫菊酯类,如丙烯菊酯、甲体氯氰菊酯、左旋反灭虫菊酯、氟氯菊酯(FMC54800)、乙氰菊酯、氟氯氰菊酯、三氟氯氰菊酯、氯氰菊酯、腈二氯苯醚菊酯、溴氰菊酯、α-氰基-3-苯基-2-甲基苄基-2,2-二甲基-3-(2-氯-2-三氟甲基乙烯基)环丙基羧酸酯、分扑菊酯、Fenfluthrin、氰戊菊酯、氟氰戊菊酯、Flumethrin、氟氨氰菊酯、氯菊酯、和反灭菊酯;硝基亚氨基化合物和硝基亚甲基化合物,如1-[(6-氯-3-吡啶基)-甲基]-4,5-二氢-N-硝基-1H-咪唑-2-胺(咪蚜胺)。有机硅化合物,优选二甲基(苯基)甲硅烷基甲基3-苯氧苄基醚,例如:二甲基-(4-乙氧基苯基)-甲硅烷基甲基-3-苯氧基苄基醚或二甲基-(苯基)-甲硅烷基甲基-2-苯氧基-6-吡啶基甲基醚、如二甲基(9-乙氧基苯基)-甲硅烷基甲基-2-苯氧基-6-吡啶基甲基醚或(苯基)[3-(3-苯氧基苯基)丙基](二甲基)-硅烷,如(4-乙氧基苯基)-[3-(4-氟-3-苯氧基苯基)-丙基]二甲基硅烷。
其它适合的活性化合物是杀藻剂,杀软体动物剂和对抗例如使船底油漆变色的“海生动物”的活性化合物。
下述实施例例示了本发明化合物制备和应用。制备实施例
实施例1
在80℃,将5.2g(20mmol)1-氯-2-(1-氯环丙基)-3-苯基-丁-3-烯-2-醇,5.2g(75mmol)1,2,4-三唑和3.4g(30mmol)权丁醇钾在50ml二甲基甲酰胺中的溶液搅拌8小时。然后,通过在减压条件下汽提溶剂浓缩反应混合物,将所剩的残留物在乙酸乙酯中吸收并用水冲洗,并用硫酸钠使有机相充分干燥,在减压条件下汽提溶剂而浓缩。采用乙酸乙酯∶环己烷=2∶1为洗脱剂,在硅胶色谱上分离剩余的残留物。浓缩洗脱物,得到1.7g(理论值的30%)的2-苯基-3-(1-氯环丙基)-3-羟基-4-(1,2,4-三唑-1-基)-丁-1-烯。1H-NMR-谱(200MHz,CDCl3,TMS)δ=0,2-0,5(m,2H);0,75-0,95(m,2H),4,43(d,J=14Hz,1H);4,9(d,J=
14Hz,1H);5,36(d,J=2Hz,1H);5,65(d,J=2Hz,1H),7,3-7,5(m,
在氩气氛和室温下将5g(25mmol)的α-溴苯乙烯的10ml无水乙醚溶液滴加到0.7g(30mmol)镁屑和10ml乙醚的搅拌混合物中。加完后,使反应混合物回流1小时。在室温下,伴随搅拌将所得格利雅溶液滴加到3g(20mmol)1-氯环丙基氯甲基酮的10ml乙醚溶液中。加完后,再将混合物回流4小时。接着用饱和氯化铵水溶液处理反应混合物,将所得混合物倒入水中,并用乙醚数次提取上述混合物。合并的有机相用饱和氯化钠水溶液冲洗。用硫酸钠充分干燥,然后在减压条件下汽提浓缩溶剂。获得5.0g(理论值的97%)1-氯-2-(1-氯环丙基)-3-苯基-丁-3-烯-2-醇。
实施例2
在80℃下伴随搅拌将59g(0.25mol)1-(1-氯环丙-1-基)-1-[3-(2-氟苯基)-丙-1-烯-2-基]-环氧乙烷的100ml二甲基甲酰胺溶液滴加到52g(0.75mol)1,2,4-三唑和8.4g(0.075mol)叔丁醇钾的500ml二甲基甲酰胺溶液中。加完后,在80℃连续搅拌18小时,接着在减压条件下浓缩反应混合物并用水处理。用乙酸乙酯提取所得混合物数次。将合并的有机相用硫酸钠充分干燥并在减压条件下浓缩。用乙酸乙酯∶环己烷=2∶1作为洗脱剂在硅胶上对剩余的残留物色谱分离。在减压条件下浓缩洗脱液,得到40g(理论值的52%2-(2-氟苯基)-3-(1-氯环丙基)-3-羟基-4-(1,2,4-三唑-1-基)-丁-1-烯。1H-NMR-谱(200MHz,CDCl3,TMS):δ=0,3-0,5(m,2H);0,8-1,0(m,2H);4,46(d,J=14Hz,1H);5,0(d,J=
14Hz,1H);5,39(d,J=1Hz,1H);5,84(d,J=1Hz,1H),7,0-7,4(m,
在0℃搅拌下将66g(033mol)碘化三甲基锍的400ml二甲基亚砜溶液滴加到9.8g(0.33mol)氢化钠,400ml二甲基亚砜和400ml四氢呋喃的混合物中。加完后,在0℃连续搅拌5分钟,然后加入70g(0.25mol)2-(2-氟苯基)-3-(1-氯环丙-1-基)-丙-1-烯-3-酮的100ml二甲基亚砜的溶液。在0℃先搅拌反应混合物15分钟然后在室温下再搅拌6小时。随后将反应混合物倒入冰水中并用乙酸乙酯数次提取用水冲洗合并的有机相,用硫酸钠充分干燥并减压浓缩,按照上述方法,获得53g(理论值的90%)油状产品1-(1-氯环丙-1-基)-1-[3-(2-氟苯基)-丙-1-烯-2-基]-环氧乙烷,不需要再纯化,可将其用于随后的合成步骤。
在室温下伴随搅拌将250ml(2.65mol)的乙酸酐滴加到106g(0.5mol)的(1-氯-环丙基)-(2′-氟苄基)酮和250ml(1.8mol)双-(二甲基氨基)-甲烷的混合物中。加完后,首先在90℃连续搅拌反应混合物1小时,然后将混合物冷却至室温并倒入冰水中。用乙酸乙酯反复提取所得混合物。用稀碳酸氢钠水溶液连续冲洗合并的有机相,然后用硫酸钠充分干燥并在减压条件下浓缩。以此方式,获得107g(理论值的95%)的2-(2-氟苯基)-3-(1-氯-环丙-1-基)丙-1-烯-3-酮的油状产物,不需要再纯化,可将其用于随后的合成步骤。
采用实施例1和2中所示的方法还可制备以下表2中列出的式(I)化合物。
实施例编号 | Zm | X | 物理常数 |
3 | 2-Cl | Cl | *) |
4 | 4-Cl | Cl | *) |
5 | 4-F | Cl | *) |
6 | 3-Cl | Cl | *) |
7 | - | F | *) |
8 | 2-Cl | F | *) |
9 | 4-Cl | F | *) |
10 | 2-OCHF2 | F | *) |
实施例3δ=0,3-0,6(m,2H);0,8-1,1(m,2H),4,40(d,J=15Hz,1H);5,02(d,J=15Hz,1H);5,37(d,J=1Hz,1H);5,90(d,J=1Hz,1H);7,0-7,5(m,4H),7,97(s,1H),8,29(s,1H)ppm
实施例4δ=0,2-0,5(m,2H),0,7-0,9(m,2H),4,41(d,J=15Hz,1 H);4,92(d,J=15Hz,1H),532(d,J=1Hz,1H);5,62(d,J=1Hz,1H),7,2-7,5(m,4H);8,01(s,1H);8,24(s,1H)ppm
实施例5δ=0,3-1,3(m,4H);3,6(d,J=15Hz,1H);4,1(d,J=15Hz,1H);5,25(s,1H);5,39(s,1H);7,0-7,5(m,4H);7,85(s,1H);8,27(s,1H)ppm
实施例6δ=0,2-1,3(m,4H);4,4(d,J=14Hz,1H);4,92(d,J=14Hz,1H);5,34(d,J=1Hz,1H);5,66(d,J=1Hz,1H);7,1-7,5(m,4H);8,0(s,1 H);8,25(s,1H)ppm
实施例7δ=0,3-0,6(m,2H);0,75-1,1(m,2H);4,43(dd,J=13 und 2Hz,1H);4,63(dd,J=13 und 2Hz 1H);5,32(d,J=1Hz,1H);5,75(d,J=1 Hz,1H);7,2-7,4(m,5H);7,95(s,1H);8,0(s,1H)ppm
实施例8δ=0,2-0,6(m,2H);0,75-1,05(m,2H);4,49(dd,J=13 und 2Hz,1H);4,86(dd,J=13 und 2Hz,1H);5,35(d,J=1Hz,1H);5,92(d,J=1Hz,1H);7,2-7,5(m,4H);7,89(s,1H);8,13(s,1H)ppm
实施例9δ=0,3-0,6(m,2H);0,75-1,05(m,2H);4,4(dd,J=13 und 2Hz,1H);4,59(dd,J=13 und 2Hz,1H);5,31(d,J=1Hz,1H);5,73(d,J=1Hz,1H);7,2-7,4(m,4H);7,97(s,1H);8,02(s,1H)ppm实施例10δ=0,4-0,6(m,2H);0,75-0,95(m,2H);4,5(d,J=15Hz,1H);4,52(s,1H);5,02(d,J=15Hz,1H);5,32(s,1H);5,71(s,1H);6,44(t,J=75Hz,1H);7,1-7,4(m,4H);8,05(s,1H);8,3(s,1H)ppm
实施例A
小麦白叶斑病试验(小麦)/保护作用溶剂:10重量份N-甲基吡咯烷酮乳化剂:0.6重量份烷基芳基聚乙二醇醚
为了生产活性化合物适合的制剂,将1重量份的活性化合物与预定量的溶剂和乳化剂混合,用水稀释浓缩物至所需浓度。
为了试验保护活性,用所示施用剂量的活性化合物的制剂向幼苗喷雾。喷雾覆盖层干燥后,用小麦白叶斑病的孢子悬浮液向植物喷雾。
将植物保持在20℃和100%相对空气湿度的温育小室中48小时。
然后将植物放置在温度约15℃和相对空气湿度大约80%的温室中。
接种10天后评价效果。
下表中给出了活性化合物,活性化合物的浓度和试验效果。
表A
小麦白叶斑病试验(小麦)/保护作用
表A-续
小麦白叶斑病试验(小麦)/保护作用
实施例B
麦类赤霉病(大麦)/保护作用溶剂:10重量份N-甲基吡咯烷酮乳化剂:0.6重量份烷基芳基聚乙二醇醚
为了生产活性化合物适合的制剂,将1重量份活性化合物与预定量的溶剂和乳化剂混合,用水稀释浓缩物至所需浓度。
为了试验保护活性,用所示施用剂量的活性化合物的制剂向幼苗喷雾。喷雾覆盖层干燥后,用大麦赤霉病的孢子悬浮液向植物喷雾。
然后将植物放置在大约20℃的温度和相对空气湿度大约100%的轻微渗透性的笼中。
接种4天后进行评价。
下表中给出了活性化合物、施用剂量和试验效果。
表B
麦类赤霉病(大麦)/保护作用
实施例C
白粉病试验(苹果)/保护作用溶剂:4.7重量份丙酮乳化剂:0.3重量份烷基芳基聚乙二醇醚
为了生产活性化合物适合的制剂,将1重量份的活性化合物与预定量的溶剂和乳化剂混合,用水稀释浓缩物至所需浓度。
为了试验保护活性,用活性化合物的制剂对幼苗喷雾直至湿透,喷雾层干燥后,用苹果白粉病(Podosphaera leucotricha)致病微生物的孢子喷粉给植物接种。
然后将植物放置在23℃和相对空气湿度大约70%的温室中。
接种10天后进行评价。
下表中给出了活性化合物,施用剂量和试验结果。
表C
黑星病试验/保护作用
实施例D
梨孢霉试验(水稻)/保护作用
溶剂:12.5重量份丙酮
乳化剂:0.3重量份烷基芳基聚乙二醇醚
为了生产活性化合物适合的制剂,将1重量份的活性化合物与预定量的溶剂和乳化剂混合,用水稀释浓缩物至所需浓度。
为了试验保护活性,用活性化合物的制剂对幼苗喷雾直至湿透。喷雾层干燥后,用稻瘟病孢子水悬浮液喷雾给植物接种。然后将植物放置在相对空气湿度100%和25℃的温室中。
接种4天后评价病害的侵染。
下表中给出了活性化合物、活性化合物浓度和试验结果。
表D
梨孢霉试验(水稻)/保护作用
实施例E
薄膜霉试验(水稻)/保护作用
溶剂:12.5重量份的丙酮
乳化剂:0.3重量份的烷基芳基聚乙二醇醚
为了生产活性化合物适合的制剂,将1重量份的活性化合物与预定量的溶剂混合,并用水和预定量的乳化剂稀释浓缩物至所需浓度。
为了试验保护活性,对3至4叶期的幼苗喷雾直至湿透。将植物保留在温室中直到喷雾覆盖层干燥,然后将用稻纹枯病接种的植物放置于25℃和相对空气湿度100%的环境中。
接种后5至8天,对病害的侵染进行评价。
下表中给出了活性化合物,活性化合物浓度和供试结果。
表E
薄膜霉试验(水稻)/保护作用
Claims (13)
2.根据权利要求1的式(I)的羟基乙基-氮杂茂环基衍生物,其中X 代表氢、氟、氯、甲基、乙基、正丙基、异丙基、甲氧基或乙氧基;Z 代表氟、氯、溴、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氯甲基、三氟甲基、二氟甲基、甲氧基、
乙氧基、三氟甲氧基、二氟甲氧基、硝基,或代表可被相同或不
同的氟和/或氯任选单取代或二取代的苯基,和m 代表0、1、2或3的数字,其中如果m代表2或3,则Z可以
代表相同或不同的基团。
子的烷氧基,Z 代表卤素、具有1至4个碳原子的烷基、具有1至4个碳原子和
1至5个卤原子的卤代烷基、具有1至4个碳原子的烷氧基、具
有1至4个碳原子和1至5个卤原子的卤代烷氧基、硝基、或被
相同或不同的卤素任选单取代至三取代的苯基,和m 代表0、1、2或3的数字。其特征在于a)使式(II)的丁烯醇衍生物其中
X、Z和m具有上述定义,和
其中
X、Z和m为上述给出的定义,在酸结合剂存在下和在稀释剂存在下与式(IV)的1,2,4-三唑反应,如果必要,然后将所得的式(I)化合物与酸或金属盐进行加成反应。
4.杀微生物组合物,其特征在于其含有至少一种根据权利要求1的式(I)羟基乙基-氮杂茂环基衍生物,或式(I)的羟基乙基-氮杂茂环基衍生物的酸加成盐或金属盐络合物。
5.应用根据权利要求1的式(I)羟基乙基-氮杂茂环基衍生物或其酸加成盐和金属盐络合物作为杀微生物剂在植物保护和材料保护中的用途。
6.在植物保护和材料保护中消灭有害微生物的方法,其特征在于将根据权利要求1的式(I)羟基乙基-氮杂茂环基衍生物或其酸加成盐或金属盐络合物施用到微生物和/或其生存环境上。
7.杀微生物剂组合物的制备方法,其特征在于将根据权利要求1的式(I)羟基乙基-氮杂茂环基衍生物或其金属盐络合物或酸加成盐与填充剂和/或表面活性物质混合。
8.式(II)的丁烯醇衍生物,其中X 代表氢、卤素、具有1至4个碳原子的烷基或具有1至4个碳原
子的烷氧基,Z 代表卤素、具有1至4个碳原子的烷基、具有1至4个碳原子和
1至5个卤原子的卤代烷基、具有1至4个碳原子的烷氧基、具
有1至4个碳原子和1至5个卤原子的卤代烷氧基、硝基、或可
被相同或不同的卤素任选单取代至三取代的苯基,m 代表0、1、2或3的数字,和Hal 代表氯或溴。
13.式(X)酮的制备方法,其中X 代表氢、卤素、具有1至4个碳原子的烷基或具有1至4个碳原
子的烷氧基,Z 代表卤素、具有1至4个碳原子的烷基、具有1至4个碳原子和
1至5个卤原子的卤代烷基、具有1至4个碳原子的烷氧基、具
有1至4个碳原子和1至5个卤原子的卤代烷氧基、硝基、或可
被相同或不同的卤素任选单取代至三取代的苯基,和m 代表0、1、2或3的数字,其特征在于使式(XII)的苄基酮其中X、Z和m为上述定义,或是α)在乙酸酐或冰醋酸存在下与式(XIII)的双-(二甲基氨基)-甲烷反应,
(CH3)2N-CH2-N(CH3)2(XIII)或是β)在催化剂存在下和在稀释剂存在下与多聚甲醛或福尔马林反应。
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DE4331476 | 1993-09-16 | ||
DEP4331476.7 | 1993-09-16 | ||
DEP4419812.4 | 1994-06-07 | ||
DE4419812A DE4419812A1 (de) | 1993-09-16 | 1994-06-07 | Hydroxyethyl-azolyl-Derivate |
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CN1133590A true CN1133590A (zh) | 1996-10-16 |
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CN94193834.4A Pending CN1133590A (zh) | 1993-09-16 | 1994-09-06 | 丁烯醇-三唑基衍生物,其制备及其作为杀微生物剂的用途 |
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US (1) | US5786375A (zh) |
EP (1) | EP0719260A1 (zh) |
JP (1) | JPH09502710A (zh) |
CN (1) | CN1133590A (zh) |
AU (1) | AU7780194A (zh) |
BR (1) | BR9407482A (zh) |
CA (1) | CA2171754A1 (zh) |
CZ (1) | CZ70096A3 (zh) |
HU (1) | HU9600660D0 (zh) |
PL (1) | PL313448A1 (zh) |
SK (1) | SK36096A3 (zh) |
TR (1) | TR27956A (zh) |
WO (1) | WO1995007896A1 (zh) |
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EP0998200B1 (de) * | 1997-07-23 | 2002-12-18 | Basf Aktiengesellschaft | Pflanzenschutzmittel-granulat mit kontrollierter wirkstofffreisetzung |
CN102639508A (zh) * | 2009-12-08 | 2012-08-15 | 株式会社吴羽 | 唑衍生物及其制造方法、该衍生物的中间体化合物及其制造方法、以及含有该衍生物的农业园艺试剂和工业材料保护剂 |
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US4927839A (en) * | 1979-03-07 | 1990-05-22 | Imperial Chemical Industries Plc | Method of preventing fungal attack on wood, hides, leather or paint films using a triazole |
AU542623B2 (en) * | 1980-05-16 | 1985-02-28 | Bayer Aktiengesellschaft | 1-hydroxyethyl-azole derivatives |
EP0117578A3 (en) * | 1983-02-23 | 1985-01-30 | Shionogi & Co., Ltd. | Azole-substituted alcohol derivatives |
US4980367A (en) * | 1987-12-17 | 1990-12-25 | E. I. Du Pont De Nemours And Company | Antifungal carbinols |
DE3784787T2 (de) * | 1986-06-23 | 1994-01-20 | Du Pont Merck Pharma | Fungizide Karbinole. |
US4952232A (en) * | 1987-04-29 | 1990-08-28 | E. I. Du Pont De Nemours And Company | Antifungal carbinols |
DE3812967A1 (de) * | 1987-06-24 | 1989-01-05 | Bayer Ag | Azolylmethyl-cyclopropyl-derivate |
DE3813874A1 (de) * | 1987-07-10 | 1989-01-19 | Bayer Ag | Hydroxyalkyl-azolyl-derivate |
DE3921481A1 (de) * | 1989-06-30 | 1991-01-03 | Bayer Ag | Hydroxyethyl-cyclopropyl-azolyl-derivate |
WO1991012000A1 (en) * | 1990-02-13 | 1991-08-22 | E.I. Du Pont De Nemours And Company | ANILINE DERIVATIVES OF α-STYRYL CARBINOLS AS ANTIFUNGAL AGENTS |
-
1994
- 1994-09-06 US US08/617,852 patent/US5786375A/en not_active Expired - Fee Related
- 1994-09-06 CA CA002171754A patent/CA2171754A1/en not_active Abandoned
- 1994-09-06 WO PCT/EP1994/002964 patent/WO1995007896A1/de not_active Application Discontinuation
- 1994-09-06 CZ CZ96700A patent/CZ70096A3/cs unknown
- 1994-09-06 AU AU77801/94A patent/AU7780194A/en not_active Abandoned
- 1994-09-06 EP EP94928316A patent/EP0719260A1/de not_active Ceased
- 1994-09-06 PL PL94313448A patent/PL313448A1/xx unknown
- 1994-09-06 CN CN94193834.4A patent/CN1133590A/zh active Pending
- 1994-09-06 SK SK360-96A patent/SK36096A3/sk unknown
- 1994-09-06 JP JP7508953A patent/JPH09502710A/ja active Pending
- 1994-09-06 BR BR9407482A patent/BR9407482A/pt not_active Application Discontinuation
- 1994-09-06 HU HU9600660A patent/HU9600660D0/hu unknown
- 1994-09-15 TR TR00942/94A patent/TR27956A/xx unknown
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SK36096A3 (en) | 1996-09-04 |
JPH09502710A (ja) | 1997-03-18 |
AU7780194A (en) | 1995-04-03 |
WO1995007896A1 (de) | 1995-03-23 |
CA2171754A1 (en) | 1995-03-23 |
US5786375A (en) | 1998-07-28 |
EP0719260A1 (de) | 1996-07-03 |
CZ70096A3 (en) | 1996-06-12 |
BR9407482A (pt) | 1996-11-12 |
HU9600660D0 (en) | 1996-05-28 |
TR27956A (tr) | 1995-11-06 |
PL313448A1 (en) | 1996-07-08 |
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