CN1031227A - 丙烯酸酯杀真菌剂 - Google Patents

丙烯酸酯杀真菌剂 Download PDF

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CN1031227A
CN1031227A CN88104241A CN88104241A CN1031227A CN 1031227 A CN1031227 A CN 1031227A CN 88104241 A CN88104241 A CN 88104241A CN 88104241 A CN88104241 A CN 88104241A CN 1031227 A CN1031227 A CN 1031227A
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CN88104241A
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CN1025649C (zh
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杰弗里·罗斯·克利夫
伊安·克理斯托弗·理查德斯
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Schering Agricultural & Chemical Products Co
Bayer CropScience Ltd Great Britain
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Schering Agricultural & Chemical Products Co
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Priority claimed from GB878716392A external-priority patent/GB8716392D0/en
Priority claimed from GB888807388A external-priority patent/GB8807388D0/en
Application filed by Schering Agricultural & Chemical Products Co filed Critical Schering Agricultural & Chemical Products Co
Publication of CN1031227A publication Critical patent/CN1031227A/zh
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
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Abstract

本发明提供了式I的化合物其中W、D、R1、R2、 R3、X、m、n、和P如说明书中所定义。该化合物具有 有价值的杀虫活性，特别是对真菌，昆虫，线虫，蜱螨 和杂草。

Description

本发明涉及具有杀真菌，杀虫，杀外寄生物或除草活性的化合物。
最近在一些出版物，特别是在欧洲专利178826    和203608中描述了具有杀真菌活性的丙烯酸衍生物。
本发明提供了式Ⅰ的化合物和其任何碱性化合物的酸加成盐类以及其任何酸性化合物的碱加成盐类
其中，
A）W是CQ，其中
a）Q是氢，R3是氢或烷基，P是1，和
（Ⅰ） n是1，m是0，x是S、O、SO、SO2、NR4、Si（OR2）R2、Si（R2）2或Si（OR2）2并且R1是R5。其中R5为可被取代的杂芳基、可被取代的杂环基、可被取代的杂环基（硫代）羰基、可被取代的链烯基、可被取代的炔基、可被取代的N-取代的亚氨基亚甲基、取代的亚杂环基甲基;或者
（Ⅱ） n为0，m为1至18，X是S而R1为R5或可被取代的芳基;或者
b）Q和R3形成一个五元或六元环的一部分，该环亦可被取代或可含其他杂原子，特别是氮，P为0或1，m和n为0至18，至少m、n和P之一要大于0;X是S、O、SO、SO2、NR2、Si（OR2）R2、Si（R2）2、或Si（OR2）2、而R1为R5或为氢、可被取代的烷基或可被取代的芳基;或者
B）W是N，在这种情况下R3是氢或烷基，m为0，P和n为1，X是O、S、NR2、Si（OR2）R2、Si（OR2）2或Si（OR2）2而R1是R5;
R2是烷基：
R4是烷基或是连接到R1的一个键而环D亦可被取代;
本发明的化合物以结构异构体存在，并且本发明包括各异构体及它们的混合物。
烷基最好是1至4个碳原子，特别是甲基或乙基。链烯基和炔基一般是3至6个碳原子。在任何烷基、链烯基或炔基上的取代基，包括卤素、烷氧基（例如具有1至4个碳原子）、卤代烷氧基（如二氟甲氧基）、羟基、烷硫基、硝基、可被取代的氨基、羧基、烷氧羰基、氰基、酸基和芳基。芳基通常为苯基，它亦可被例如卤素、可被取代的烷基或烷氧基、芳基、芳氧基、硝基、氨基、COOH、COOR2、CN、CONR2R2或S（O）nR2所取代。术语杂芳基和杂环基包括基团例如噻吩基、呋喃基、吡啶基、嘧啶基、吡唑基、噻唑基、噻唑啉基、噻唑酮、噁唑基、苯并咪唑基、四唑基、苯并噁唑基、噻二唑基、二氧戊环基、咪唑并吡啶基、1，3-苯并噁嗪基、1，3-苯并噻嗪基、噁唑并吡啶基、三唑基、三嗪基、咪唑基、吗啉代、苯并呋喃基、吡唑啉基、喹啉基、喹唑啉基、二氢喹唑啉基或苯并噻唑基，它们本身亦可如苯基一样被取代。环D亦可以如苯基中所述的相似方式以及被羧基、烷氧羰基、磺酰基和磺酰氨基所取代。术语“酰基”包括磺酸和含磷酸以及羧酸的残基。酰基最好是如1至4个碳原子的烷酰基，氨基亦可被例如一个或二个烷基所取代或二个取代基可形成一个环，例如形成吗啉代或哌啶子基环。亚氨基亚甲基亦可在氮和碳上取代。氮上取代基的例子包括芳基和烷基。碳上取代基的例子包括芳基，烷基，烷硫基，烷氧基和氰基。
化合物的特别好的基团是那些基团，其中n为1，p为1，m为0，W为CH或N，R2和R3为甲基，X为硫而R1为杂芳基。
本发明的化合物是特别有价值的杀真菌剂，特别是对植物的真菌病，如霉病，尤其是对禾白粉菌（Erysiphe    graminis）、葡萄生单轴霉（Plasmopara    viticola）、稻瘟病（pyricularia    oryzae）、
禾眠斑病（pseudocercosporella    herpotrichoides）、
佐佐木薄膜革菌（pellicularia    sasakii）、
灰葡萄孢（Botrytis    cinerea）、
猝倒病菌（Rhizoctonia    solani）、
隐匿柄诱菌（Puccinia    recondita）、
致病疫霉（Phytophthora    infestans）、
和苹果黑星菌（Venturia    inaequalis）。这些化合物对其也可能有效的其他真菌包括：其他的白粉菌、其他锈菌以及半知菌纲、子囊菌纲、藻状菌纲和担子菌纲的一般病原体。
本发明的化合物也具有杀虫、杀蜱螨和杀线虫活性，并且可特别有效的防治各种经济上重要的昆虫、蜱螨和植物线虫，包括动物的外寄生物，尤其是双翅目，例如丝光绿蝇（Lucilia    sericata）和家蝇（Musca    domestica）;鳞翅目，包括小菜蛾（Plutella    xylostella）、海灰翅夜蛾（Spodoptera    littoralis）、棉铃虫（Heliothis    armigera）和大菜粉蝶（Pieris    brassicae）;同翅目，包括蚜虫例如蚕豆修尾蚜（Megoura    viciae）;鞘翅目，包括叶甲（Diabrotica    spp.）例如黄瓜十一星叶甲（Diabrotica    undecimpunctata）和螨，例如红叶螨属害虫（Tetranychus    spp.）。
它们也具有除草活性。
因此本发明也提供了在受害虫侵扰或易受害虫侵扰的地区防治害虫（即真菌，昆虫，丝虫，蜱螨和杂草）的方法，它包括对该地区施用式Ⅰ的化合物。
本发明也提供了含有式Ⅰ化合物的农用组合物，它是该化合物与可供农业用的稀释剂或载体的混合物。
本发明的组合物当然可以包括多种本发明的化合物。
此外，该组合物可包括一种或多种其他的活性组份，例如已知的具有植物生长调节，除草，杀真菌，杀虫或杀蜱螨性质的化合物。另一方面，本发明的化合物可顺序与其他活性组份一起使用。
本发明的组合物中的稀释剂或载体可以是固体或液体，亦可加入表面活性剂，例如分散剂，乳化剂或湿润剂。合适的表面活性剂包括阴离子化合物如羧酸盐，例如长链脂肪酸的金属羧酸盐;N-酰基肌酸盐;磷酸与脂肪醇乙氧基化物的单或双酯或这些酯的盐;脂肪醇硫酸酯盐如十二烷基硫酸钠，十八烷基硫酸钠或十六烷基硫酸钠;乙氧基化的脂肪醇硫酸酯盐;乙氧基化的烷基酚硫酸酯盐;木质素磺酸盐;石油磺酸盐;烷基-芳基磺酸盐如烷基-苯磺酸盐或低级烷基萘磺酸盐，例如丁基-萘磺酸盐;磺化的萘-甲醛缩合物的盐;磺化的酚-甲醛缩合物的盐;或者更复杂的磺酸盐如酰胺磺酸盐（例如油酸和N-甲基牛磺酸的磺化缩合产物）或磺基丁二酸二烷基酯盐（例如丁二酸二辛酯的磺酸钠）。非离子型剂包括脂肪酸酯类、脂肪醇类、脂肪酸酰胺类或脂肪烷基-或链烯基取代的酚类与环氧乙烷的缩合产物，多元醇醚类的脂肪酯类（例如脱水山梨糖醇脂肪酸酯），这些酯与环氧乙烷的缩合产物（例如聚氧乙烯脱水山梨糖醇脂肪酸酯），环氧乙烷和环氧丙烷的嵌段共聚物，炔二醇如2，4，7，9-四甲基-5-癸炔-4，7-二醇，或乙氧基化的炔二醇。
阳离子表面活性剂的例子包括，例如作为醋酸盐，环烷酸盐或油酸盐的脂肪族单一、二-或多胺;含氧胺如胺氧化物或聚氧乙烯烷基胺;通过羧酸与二或多胺缩合制得的酰胺键合的胺;或季铵盐。
本发明的组合物可采用本专业中所熟知的用于农业化学制剂的任何剂型，例如，溶液，分散体，水乳浊液，撒布粉，拌种剂，熏蒸剂，烟剂，毒饵，可分散的粉剂，乳油或粒剂。此外，它可以是供直接使用的适当剂型，或是作为浓缩物或初级组合物的形式，这些浓缩物或初级组合物在使用前需要用适当量的水或其他稀释剂稀释。
乳油包括溶在与水不相混溶的溶剂中的本发明的化合物，它在乳化剂的存在下可与水    形成乳液。
撒布粉包括与固体粉状的稀释剂（例如白陶土）在一起致密的混合和研磨的本发明的化合物。
粒状固体包括与可用在撒布粉中的那些相同的稀释剂混合在一起的本发明的化合物，但该混合物是用已知的方法制粒的。此外，它还可包括被吸附的或者吸附在预制粒的稀释剂（例如漂白土，活性白土或石灰石粗砂）上的活性组份。
可湿性粉末，颗粒剂或粒剂通常包括的活性组份是与适当的表面活性剂和惰性粉末稀释剂（例如中国白陶土）形成的混合物。
另一种适当的原液是悬浮剂原液，它是通过将化合物与水或其他液体，一种湿润剂和一种悬浮剂研磨而制成的。
本发明的组合物中的活性组份的浓度，当用于植物时最好是在0.001到3.0%（重量）范围内，特别是0.01到1.0%（重量）。在初级组合物中活性组份的量可很大地变化，例如，可为组合物的5到95%（重量）。
在本发明的方法中一般是将化合物施用到种子，植物或它们的生境上。因此，可以在条播之前，条播时或之后将该化合物直接施用在土壤中，使得土壤中存在的活性化合物可以控制侵蚀种子的真菌的生长。当直接处理土壤时可用任何方式施用该活性化合物以使它紧密地与土壤混合，例如通过喷雾，通过散播固体剂型的粒剂，或者在条播的同时施用活性化合物以使它能在与播种同一垄沟中施入。合适的施用率范围是从0.05至20公斤/公顷，最好是0.1到10公斤/公顷。
另一方面，亦可将该活性化合物通过下式方法直接施用于植物上，例如，当真菌开始在植物上出现时，或在真菌出现前作为一个预防措施将该化合物进行喷雾或散粉。在二种情况下最好的施用方式是叶上喷雾。一般重要的是在植物生长的早期阶段能很好地控制真菌，因为在这个时候植物可被最严重损坏。如果认为必要，喷雾或散粉时亦可方便地含有出芽前和出芽后的杀草剂，有时，在种植前或种植期间，处理植物的根也是实用的，例如通过将根浸入适当的液体或固体组合物中。当将活性化合物直接施用于植物时，合适的施用率是0.01到10公斤/公顷，最好是0.05～5公斤/公顷。
本发明的化合物可用各种方法制备，例如，通过将式Ⅱ的化合物与式Ⅲ的化合物反应，
其中Z为离去基团，例如卤素。
此外，当W是CH时，亦可将式（Ⅳ）的化合物与式Ⅴ的甲酸酯在碱性条件下反应。
Figure 881042412_IMG7
X为SO或SO2的化合物可通过用一种适当的氧化剂（例如间-氯代过苯甲酸）氧化其中X为S的化合物而制得。其他的方法对于本专业的化学家来说是显而易见的，而制备起始原料和中间体的方法也是熟知的。实例也说明了制备本发明的化合物以及起始原料和中间体的各种方法。
本发明用下述实例进行说明。各个新化合物的结构是用元素分析和/或其他合适的分析方法确证的。温度为℃。
实例1
将邻-甲苯乙酸甲酯（100克）溶解在甲酸甲酯（450毫升）和二甲基甲酰胺（200毫升）的混合物中。在冷却下将该溶液加入至用汽油洗涤过的氢化钠（36.5克的于油中的80%分散体）在二甲基甲酰胺（100毫升）的悬浮液中。然后该混合物在室温下搅拌过夜。蒸去过量的甲酸甲酯和大部分二甲基甲酰胺并加入水（500毫升）。混合物用乙醚处理并分出水相，酸化并用乙醚萃取。该萃取液用常用的方法后处理后，得到棕色油。将它溶在四氢呋喃中并在冷却下将该溶液滴加到氢化钠（16.5克的于油中的80%分散体）在四氢呋喃（50毫升）溶液中。当无更多的氢气逸出时，加入碘代甲烷（35毫升）并将混合物加热回流5小时。加入甲醇（5毫升）并蒸去溶剂。所得的油分配在乙醚和水间并将有机相按常用的方法后处理，得到（Z）-3-甲氧基-2-（邻-甲苯基）丙-2-烯酸甲酯，m.p.68-70℃。将该产物（185克）溶在四氯化碳内（1250毫升），加入N-溴代琥珀酰亚胺（159.3克）并将混合物加热回流3小时。然后冷却该反应混合物并进行后处理，得到淡棕色油。将粗产品用二异丙醚在轻石油醚中的10%溶液研制，得到（E）-3-甲氧基-2-〔（2-溴甲基）苯基〕丙-2-烯酸甲酯，m·p·87-90℃。将2-巯基苯并噻唑（101.87克）在四氢呋喃（600毫升）中的溶液于搅拌下滴加至用汽油洗涤过的氢化钠（自18.42克的于油中的80%分散体）在四氢呋喃（200毫升）的悬浮液中。该混合物加热回流30分钟并冷至室温。用1小时加入溴甲基化合物（175克）于四氢呋喃（1000毫升）中的溶液并将该混合物在室温下搅拌5小时。加入四氢呋喃水溶液以平息反应物并将该混合物进行蒸发。残余物按常用的方法进行后处理，得到（E）-2-〔2-〔〔（2-苯并噻唑基）硫代〕甲基〕苯基〕-3-甲氧基-2-丙烯酸甲酯。m·p·77-78°（化合物1）。
实例2
将碳酸钾（25克）加入至搅拌着的邻-甲苯基乙酸（7.5克）在乙腈（125毫升）的溶液中。该混合物在室温下搅拌10分钟。加入氯乙酸乙酯（6.13克）并将该混合物加热回流过夜。然后倾入水中，用浓盐酸酸化至pH2并用乙酸乙酯萃取。该萃取液用盐水洗涤，干燥并蒸发，用色谱柱纯化，得到邻-甲苯基乙酸乙氧羰基甲基酯。将碳酸钾（15克）加入至搅拌着的该产物（10克）在二甲基甲酰胺（100毫升）的溶液中。该混合物在室温下搅拌72小时，然后加热回流过夜。将混合物冷却至0℃并加入碳酸钾（5克），随之加入碘代甲烷（2.65毫升）。该混合物在室温下搅拌24小时。将混合物倾入水中，用乙醚萃取，该萃取液用盐水洗涤，干燥和蒸发，得到3-（2-甲基苯基）-4-甲氧基-呋喃-2（5H）-酮，为胶状物。然后将其用N-溴代琥珀酰亚胺处理，随之再与2-巯基苯并噻唑反应，方法与实例1所述相同。得到3-〔2-〔〔（2-苯并噻唑基）硫〕甲基〕苯基〕-4-甲氧基呋喃-2（5H）-酮，m·p·81-82°（化合物2）。
实例3
将苯并〔b〕噻吩-2（3H）-酮（6克）和氢氧化钠（3.2克）在水中（40毫升）回流1小时。加入4-氯苄基氯（6.44克）并将该混合物再继续回流1.5小时，然后冷却过夜。加入水（25毫升），随之加入乙酸（100毫升）。收集固体，用水洗涤并干燥，得到〔2-（4-氯代苄硫基）苯基〕乙酸，m.p.149-151℃。将该产品（10.4克）于含有浓硫酸（0.5毫升）的甲醇（250毫升）中的溶液加热回流过夜，蒸去过量的甲醇。加入醚和水并用氢氧化钠水溶液洗涤有机层，干燥并蒸发。固化的产品用己烷重结晶，得到起始酸的甲酯，m·p·52-54℃。按与实例1中所述相同的方法将它用甲酸甲酯和氢化钠处理，得到（E）-3-甲氧基-2-〔2-（4-氯代苄硫基）苯基〕丙-2-烯酸甲酯，m.p.81-84℃（化合物3）及其相应的Z-异构体，m·p·127-128℃（化合物4）。它们是用硅胶柱层析分离的。
实例4
在氮气下，用1小时将氯氧代乙酸甲酯（22.5毫升）在四氢呋喃（60毫升）中的溶液滴加到搅拌着的咪唑（33.35克）在四氢呋喃（500毫升）中的溶液并维持在0℃。然后将该混合物在该温度下再搅拌1小时。过滤该反应混合物并用四氢呋喃洗涤沉淀。含有α-氧代-1H-咪唑-1-乙酸甲酯的滤液和洗涤液冷却至-65℃，并用45分钟将由邻-溴甲苯（42克），1，2-二溴乙烷（3.6毫升）和镁（7克）在四氢呋喃中制备的格氏试剂溶液加入同时维持温度在-60至-70℃之间。然后将该混合物在该温度下搅拌15分钟之后在室温下搅拌2.5小时。然后倾入冰/水中，用乙醚萃取，该萃取液用盐水洗涤，干燥并浓缩。残留物在减压下蒸馏，得到氧代（邻-甲苯基）乙酸甲酯，沸点92-97℃/0.5mm。该产物（5克）在甲醇（100毫升）中的溶液与甲氧基胺盐酸盐（2.55克）一起加热回流3小时。冷却该混合物，蒸发，用二异丙醚研制，过滤并将滤液蒸发，得到（甲氧亚氨基）（邻-甲苯基）乙酸甲酯。然后在回流和300瓦灯下将它用N-溴代琥珀酰亚胺在四氯化碳中处理并加入过氧化苯甲酰（每10分钟0.005克）。用常用的方法后处理，得到溴甲基化合物，然后将它按与实例1所述相同的方法与2-巯基苯并噻唑反应，得到〔2-〔〔（2-苯并噻唑基）硫〕甲基〕苯基〕（甲氧亚氨基）乙酸甲酯，m.p.113-114℃（化合物5）。
按前面实例之一中所述相同的方法，可得到如下化合物：化合物为E-式，除非另有说明。
化合物 R1Xpm n 熔点
号
6.    6-EtO-苯并噻唑-2-基    S    0    1    100-101
7.    苯并噁唑-2-基    S    0    1    油
8.    1-Me-咪唑-2-基    S    0    1    102-104
9.    4-Me-嘧啶-2-基    S    0    1    94-95
10. 4，6-Me2-嘧啶-2-基 S 0 1 油
11. 4-Bt u-1H-咪唑-2- S 0 1 玻璃状
基
12.    （MeS）（3-甲基-5-氧代    S    0    1    129-131
-1-Ph-吡唑啉-4-亚
基）甲基
13.    嘧啶-2-基    S    0    1    75-76
14.    2-噻唑啉-2-基    S    0    1    105-106
15.    5-MeCO-苯并噻唑-2-    S    0    1    109-110
基
16.    Ph    （Z-异构体）    S    1    0    92-4
17. 5-CF3-苯并咪唑-2-基 S 0 1 油
18.    1-Ph-四唑-5-基    S    0    1    126-127
19. 5-CF3-苯并噻唑-2-基 S 0 1 97-99
化合物 R1Xpm n 熔点
号
20.    Ph.    S    1    0    71-74
21. 4，4-Me2-5-亚甲基- S 0 1 101
2-噻唑啉-2-基
22.    5-Ph-嘧啶-2-基    S    0    1    105-106.5
23.    6-Cl-4-甲基-苯并噻    S    0    1    89-91
唑-2-基
24.    5-Me-苯并噻唑-2-基    S    0    1    83-85
25.    5-氨基苯并噻唑-2-基    S    0    1    胶状物
26.    4-Cl-苯并噻唑-2-基    S    0    1    152-154
27.    2-吡啶基    S    0    1    80-82
28. 1-（3-NO2-Ph）四唑- S 0 1 93-95
5-基
29.    2-噻吩基    S    0    1    64-65
30.    5-Me-苯并噁唑-2-基    S    0    1    90-91
31.    3-CN-4-COOEt-6-Me-    S    0    1    113-114
32.    7-Cl-苯并噻唑-2-基    S    0    1    132-134
33. 5，6-Cl2-1H-苯并咪唑 S 0 1 169.5-171
-2-基
34.    5-Cl-苯并噁唑-2-基    S    0    1    105-107
35.    6-Cl-苯并噻唑-2-基    S    0    1    110-112
36.    1-MeS-2-CN-2-COOMe-    S    0    1    85-85
乙烯基
化合物 R1Xpm n 熔点
号
37. 5-（2-NO2-亚苄基）- S 0 1 177-178.5
4-氧代-2-噻唑啉-2-基
38.    4-OH-5-Me-6-丙基嘧    S    0    1    169-170
啶-2-基
39.    咪唑并〔1，5-a〕吡啶-    S    0    1    77-79
3-基
40.    4-Ph-噻唑-2-基    S    0    1    油
41.    5-炔丙基硫-1，3，4-    S    0    1    油
噻二唑-2-基
42. 3-CN-4，6-Me2-2 S 0 1 140-142
-吡啶基
43.    3-MeO-Ph    S    0    1    87-89
44.    3-MeO-Ph（Z-异构体）    S    1    0    95-97
45.    1-丙基苯并咪唑-2-基    S    0    1    68-70
46.    4-叔丁基-Ph    S    1    0    油
47.    4-吡啶基    S    0    1    101-103
48.    1-苄硫基-2，2-二氰基    S    0    1    97-98
-乙烯基
49.    1-Me-5-MeS-苯并咪唑    S    0    1    90-92
-2-基
50.    1-Ph-1，2，4-三唑    S    0    1    油
-3-基
化合物 R1Xpm n 熔点
号
51.    1-异丙基苯并咪唑-2-基    S    0    1    油
52.    5-Br-苯并噻唑-2-基    S    0    1    124-124.5
53.    5-Br-1H-苯并咪唑-    S    0    1    179-180
2-基
54. 2，2-Me2-1，3-二氧 S 1 0 油
戊环-4-基
55. 2，2-Me2-1，3-二氧 S 1 0 油
戊环-4-基（Z-异构体）
56.    Ph.    S    2    0    油
57.    Ph（Z-异构体）    S    2    0    油
58.    7-Cl-4-MeO-苯并噻唑    S    0    1    胶状物
-2-基
59.    1H-苯并咪唑-2-基    S    0    1    166-168
60.    5-Cl-苯并噻唑-2-基    S    0    1    109-110
61. 5-NO2-苯并噁唑-2-基 S 0 1 120-122
62.    5-叔丁基-苯并噁唑-2-    S    0    1    85-87
基
63.    5-EtS-1-Me-苯丙咪唑    S    0    1    胶状物
-2-基
64. 4，6，7-Cl3-苯并噻唑 S 0 1 159-161
-2-基
65.    5-苯基噻唑-2-基    S    0    1    油
化合物 R1Xpm n 熔点
号
66. 5，7-Me2-苯并噁唑-2 S 0 1 97-98
-基
67.    6-Me-苯并噁唑-2-基    S    0    1    70-73
68.    吗啉代硫代甲基    S    0    1    97-99
69.    4-Cl，3-MeO-苯基    S    1    0    油
70.    1，2，4-三唑-1-基    S    1    0    油
71.    3-甲氧基苯基    S    2    0    油
72. 5，7-Cl2-2，3-二氢 S 1 0 油
苯并呋喃-2-基
73.    Ph-CH＝CH    S    1    0    油
74.    1，2，4-三嗪-3-基    S    1    0    163
75.    嘧啶-4-基    S    0    1    101
76.    2-Me-1，3-二氧戊环    S    1    0    油
-2-基
77.    6-丙基苯并噻唑-2-基    S    0    1    油
78.    6-苯氧基苯并噻唑-2-基    S    0    1    124-126
79.    5-MeCONH-苯并噻唑-2    S    0    1    151-153
-基
80.    4Ph-Ph    S    1    0    131-133
81. Bt u-C≡C S 2 0 76-77
82. Bt u-C≡C（Z-异构体） S 2 0 油
83.    4-（4-Cl-PhO）-Ph    S    1    0    109-113
化合物 R1Xpm n 熔点
号
84.    3-吡啶基    S    1    0    油
85.    4-氧代-3，4-二氢嘧啶    S    0    1    163
-2-基
86.    5-PhCONH-苯并噻唑-2    S    0    1    100
-基
87.  5-（1，3-苯并二氧戊环    S    0    1    泡沫状
-5-基亚甲基-氨基）苯并
噻唑-2-基
88.    4-氧代-3，4-二氢喹唑    S    0    1    223-226
啉-2-基
89.    喹啉-2-基    S    0    1    88-90
90.    3-甲基苯并噻唑-2（3H）    N＝0    1    139-141
亚基
91.    4-（4-Cl-PhO）-Ph    S    1    0    148-151
（Z-异构体）
92.    5-苯基-1，2，4-三嗪    S    0    1    167
-3-基
93.    3-苯基-1，2，4-噻二    S    0    1    油
唑-5-基
94.    2-苯基-1，3-二氧戊环    S    1    0    油
-2-基
95.    2-苯基-1，3-二氧戊环    S    1    0    120-122
-2-基（Z-异构体）
化合物 R1Xpm n 熔点
号
96.    5-PhCH＝N-苯并噻唑-    S    0    1    胶状物
2-基
97.    5-PhN＝CH（MeS）    S    0    1    胶状物
98.    4-（4-Cl-Ph）-噻唑-    S    0    1    99-102
2-基
99.    4-（4-Me-Ph）-噻唑-    S    0    1    胶状物
2-基
100.    5-甲基-4-苯基-噻唑-    S    0    1    88-91
2-基
101.    5-Cl-1-H-苯并咪唑    S    0    1    161-164
-2-基
102.    3-Me-4-氧代-3，4    S    0    1    144-146
-二氢喹唑啉-2-基
103.    4-Me-5-苯基噻唑-2    S    0    1    油
-基
104.    2H-1，4-苯并噻嗪-3    S    0    1    油
-基
105.    2H-1，4-苯并噁嗪-3    S    0    1    油
-基
106.    6-Cl-噁唑〔4，5-b〕    S    0    1    114-116
吡啶-2-基
107.    5-Cl-1-甲基苯并咪唑    S    0    1    132-135
-2-基
按实施例4中所述的相同方式，可得到如下化合物：
Figure 881042412_IMG9
化合物 R1Xpm n 熔点
号
108.    5-氯苯并噻唑-2-基    S    0    1    110-111
109.    苯并噁唑-2-基    S    0    1    111-113
按实施例2中所述的相同方式也可得到4-甲氧基-3-〔2-（苯硫基甲基）苯基呋喃-2（5H）-酮（化合物110）。
实例5
本实例阐明了可用本发明的化合物配制的典型的原液。
a）可湿性粉剂
本发明的化合物    25%    W/W
木素磺酸钠    5%    W/W
硅石    5%    W/W
中国白陶土    65%    W/W
b）乳油
本发明的化合物    250克/升
Soprophor Bsu1200克/升
N-甲基吡咯啉酮    657克/升
1（三苯乙烯基酚乙氧基化物非离子乳化剂）
实验实例A
测定化合物对下述1个或多个样本的活性：
a）叶的实验
致病疫霉（Phytophthora    infestans）（PI）
葡萄生单轴霉（Plasmopara    viticola）（PV）
禾白粉菌（Erysiphe    graminis）（EG）
稻瘟病（Pyricularia    oryzae）（PO）
佐夕木薄膜革菌（Pellicularia    sasakii）（PS）
灰葡萄孢（Botrytis    cinerea）（BC）
苹果黑星菌（Venturia    inaequalis）（VI）
隐匿柄锈菌（Puccinia    recondita）（PR）
在所需浓度下将该化合物的水溶液或分散体，包括湿润剂，通过喷雾或通过浸透试验植物的基基处而施用。然后用合适的试验病原体接种到这些植物上，并放在适于维持植物生长和疫病发展的控制环境条件下。在一适当时间后，用目视测定叶子表面的感染程度。
如果在125ppm（w/v）或更低的浓度下化合物能控制大于50%的疾病，则认为化合物是有效的。
b）土壤病原体试验
在本试验中测定化合物对立枯丝核菌（Rhizoctonia    solani）（RS）的活性。
含有玉米粉/砂的烧瓶用试验真菌接种而后培养。用该玉米粉/砂培养物感染盆堆肥而后将它们装入塑料盆内。将该化合物的水溶液或分散体，包括湿润剂，加入到盆内并使每个盆达到所需的化合物浓度。通过加入相同的溶液和分散剂但不含试验化合物而设置对照盆。在每个盆施用试验化合物后立即播种一些洋白菜种子。用处理过的感染过的土壤埋上这些种子并把盆放在适于植物生长和疾病发展的控制环境条件下培养。计算长出的洋白菜的菜苗数目并通过与未处理的但感染了的盆比较来计算控制疾病的百分数。
如果在100ppm（重量/土壤体积）或更低的浓度下化合物能控制大于50%的疾病，则认为化合物是有效的。
下表表示这些化合物的活性（+＝有效）。
化合物号    PI    PV    EG    PO    PS    BC    VI    RS    PR
1    +    +    +    +    +    +
2    +
3    +    +    +    +    +    +
4    +
6    +    +    +    +    +
7    +    +    +    +    +
8    +
9    +    +    +    +    +
10    +    +    +    +    +
11    +
12    +    +
13    +    +    +    +
14    +    +    +    +
15    +    +    +    +    +    +
16    +    +    +
17    +    +
18    +
19    +    +    +    +
20    +    +    +
21    +    +    +    +    +
22    +    +    +    +    +    +    +    +
23    +    +    +    +    +    +    +
24    +    +    +    +    +    +    +    +
25    +    +    +    +    +    +
26    +    +    +    +    +    +
27    +    +    +    +    +
28    +    +    +
29    +    +    +    +
30    +    +    +    +    +    +    +    +
31    +    +    +    +
32    +    +    +    +    +
化合物号    PI    PV    EG    PO    PS    BC    VI    RS    PR
33    +    +    +
34    +    +    +    +    +    +
35    +    +    +    +
36    +    +
37    +
38    +
39    +
40    +    +    +    +    +
41    +    +
42    +    +    +    +
43    +    +    +    +
44    +    +
45    +    +    +    +
46    +    +
48    +
49    +    +    +    +    +    +    +    +
50    +    +    +
51    +    +    +
52    +    +    +    +    +    +
53    +    +
56    +    +
57    +    +
59    +    +
60    +    +    +    +    +    +
61    +    +    +
62    +    +    +    +    +    +
63    +
64    +
65    +    +    +
66    +    +    +    +    +
67    +    +    +
69    +
化合物号    PI    PV    EG    PO    PS    BC    VI    RS    PR
70    +
71    +
73    +    +    +    +
74    +
75    +    +
76    +    +    +    +    +
77    +    +    +    +    +
78    +    +    +    +    +
79    +    +
80    +    +
81    +    +    +
82    +    +    +
83    +
101    +    +
实验实例B
本例子说明了本发明的化合物的杀虫活性。
将1毫升的含各种浓度的试验化合物的丙酮溶液加在1厘米×2厘米的带齿的棉毛卷上，并放入2厘米直径×5厘米长的玻璃小瓶内。干燥后，然后将处理过的材料用1毫升营养液浸泡，并用丝光绿蝇（Lucilia sericata）的第一龄幼虫感染，塞上棉塞并在25℃下保持24小时。对照物的死亡率小于5%，而实例6、13、15、19、21-24、30、32、34、35、40、49、52、60和61的化合物的LC50小于300ppm。

Claims (3)

1、一种防治害虫的农用组合物，包括式Ⅰ的化合物和其任何碱性化合物的酸加成盐类以及其任何酸性化合物的碱加成盐类，所说的化合物是在其与可供农用的稀释剂或载体所形成的混合物中。
Figure 881042412_IMG2
其中，
A)W是CQ，其中
a)Q是氢，R3是氢或烷基，P是1，和
(i)n是1，m是0，X是S、O、SO、SO2、NR4、Si(OR2)R2、Si(R2)2或Si(OR2)2而R1是R5，其中R5为可被取代的杂芳基、可被取代的杂环基、可被取代的杂环基(硫代)羰基、可被取代的链烯基、可被取代的炔基、可被取代的N-取代的亚氨基亚甲基、取代的亚杂环基甲基；或者
(ii)n为0，m为1至18，X是S而R1为R5或可被取代的芳基；或者
b)Q和R3形成一个五元或六元环的一部分，该环亦可被取代或可含其他杂原子，特别是氮，p为0或1，m和n为0至18，至少m、n和p之一要大于0；X是S、O、SO、SO2、NR2、Si(OR2)R2、Si(R2)2或Si(OR2)2，而R1为R5或为氢、可被取代的烷基或可被取代的芳基；或者
B)W是N，在这种情况下R3是氢或烷基，m为0，p和n为1，
X是O、S、NR2、Si(OR2)R2、Si(R2)2或Si(OR2)2而R1荝5；
R2是烷基；
R4是烷基或是连接到R1的一个键，而环D亦可被取代。
2、权利要求1的组合物，其中n为1，P为1，m为0，W为CH或N，R2和R3为甲基，X为S，而R1为杂芳基。
3、式Ⅰ化合物的制备方法，它包括将式Ⅱ的化合物与式Ⅲ的化合物反应;
Figure 881042412_IMG3
式Ⅱ中Z为离去基团，如卤素，
或者，当W为CH时，将式Ⅳ的化合物与式Ⅴ的甲酸酯在碱性条件下反应;或者，如果要得
到其中X为SO或SO2的化合物，则可氧化其中X为S的化合物;并且亦可将任一酸或碱的化合物形成盐。
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KR100427262B1 (ko) * 2001-07-16 2004-04-14 한국화학연구원 살균활성을 가지는 유황함유 메톡시 아크릴레이트 유도체
ITMI20020814A1 (it) 2002-04-17 2003-10-17 Isagro Ricerca Srl Nuovi analoghi delle strobilurine e loro uso quali acaricidi e insetticidi
CN1789253A (zh) * 2005-12-28 2006-06-21 华中师范大学 一类苯并噻唑衍生物的合成及杀菌活性
CN101311170B (zh) 2007-05-25 2010-09-15 中国中化股份有限公司 取代嘧啶醚类化合物及其应用
CN101268780B (zh) * 2008-05-08 2010-07-21 华中师范大学 一种甲氧基丙烯酸酯类杀菌剂、制备方法及用途
CN101906075B (zh) 2009-06-05 2012-11-07 中国中化股份有限公司 含取代苯胺基嘧啶基团的e-型苯基丙烯酸酯类化合物及其应用
CN108314656B (zh) 2018-02-27 2020-10-27 浙江工业大学 不饱和烃嘧啶硫醚类化合物及其制备方法与应用

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CN101205187B (zh) * 2006-12-22 2011-04-27 中国中化股份有限公司 取代芳基醚类化合物及其制备与应用

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KR960012207B1 (ko) 1996-09-16
HU204658B (en) 1992-02-28
HUT47373A (en) 1989-03-28
DE3856431D1 (de) 2000-11-16
AU1880688A (en) 1989-01-12
DK381588D0 (da) 1988-07-08
PT87938B (pt) 1995-03-01
US5304530A (en) 1994-04-19
EP0299694A2 (en) 1989-01-18
ATE196900T1 (de) 2000-10-15
FI92392B (fi) 1994-07-29
KR890002091A (ko) 1989-04-08
NZ225339A (en) 1990-05-28
TR24201A (tr) 1991-07-01
PT87938A (pt) 1989-06-30
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YU47288B (sh) 1995-01-31
DE3856431T2 (de) 2001-02-08
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AU607235B2 (en) 1991-02-28
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YU131888A (en) 1990-12-31
IL87020A (en) 1996-09-12
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