CN1278254A - 噻二唑羧酰胺衍生物、植物病害防治剂及其使用方法 - Google Patents
噻二唑羧酰胺衍生物、植物病害防治剂及其使用方法 Download PDFInfo
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- CN1278254A CN1278254A CN98810756A CN98810756A CN1278254A CN 1278254 A CN1278254 A CN 1278254A CN 98810756 A CN98810756 A CN 98810756A CN 98810756 A CN98810756 A CN 98810756A CN 1278254 A CN1278254 A CN 1278254A
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Abstract
N－(3－氯－4－甲基苯基)－4－甲基－1,2,3－噻二唑－5－羧酰胺。特征在于含有上述化合物作为活性成分的植物病害防治剂;和其使用方法。此药剂对植物病害如稻瘟病具有优异的活性。
Description
技术领域
本发明涉及噻二唑羧酰胺、植物病害防治剂及其应用。
背景技术
JP-A-8-325110描述了包括本发明化合物的1，2，3-噻二唑衍生物用作植物病害防治剂。然而，此文献未公开本发明的N-(3-氯-4-甲基苯基)-4-甲基-1，2，3-噻二唑-5-羧酰胺。
发明描述
本发明者潜心研究以开发出新的植物病害防治剂，结果发现本发明的N-(3-氯-4-甲基苯基)-4-甲基-1，2，3-噻二唑-5-羧酰胺是迄今在任何文献中都未知的化合物，并且与JP-A-8-325110中公开的化合物相比，它是一种在低剂量下对(特别是)如下作物的病害更有效：稻(特别是稻瘟病)、大麦、小麦、燕麦、黑麦、蔬菜等，且药害更低和对哺乳动物毒性更低的化合物，由此而完成了本发明。即，本发明涉及N-(3-氯-4-甲基苯基)-4-甲基-1，2，3-噻二唑-5-羧酰胺、含有此化合物作为活性成分的植物病害防治剂和此植物病害防治剂的应用。
本发明的N-(3-氯-4-甲基苯基)-4-甲基-1，2，3-噻二唑-5-羧酰胺可以通过例如JP-A-8-325110中公开的方法制备。
本发明的N-(3-氯-4-甲基苯基)-4-甲基-1，2，3-噻二唑-5-羧酰胺可用作植物病害防治剂且在防治各种病害，例如细菌性病害方面非常有效，例如，稻瘟病(Pyricularia oryzae)、稻纹枯病(Rhizoctoniasolani)、稻胡麻斑病(Cochiobolus miyabeanus)，各种宿主植物上的白粉病，如大麦和小麦白粉病(Erysiphe graminis)，燕麦冠锈病(Puccinia coronata)，其它植物锈病，蕃茄晚疫病(Phytophthorainfestans)，其它植物的晚疫病或疫病，各种植物的霜霉病，如黄瓜霜霉病(Pseudoperonospora cubensis)和葡萄霜霉病(Plasmoparaviticola)，苹果黑星病(Venturia inaequalis)，苹果轮斑落叶病(Alternaria mali)，梨黑斑病(Alternaria kikuchiana)，柑桔褐蒂腐病(Diaporthe citri)，由假单胞菌引起的病害，如黄瓜细菌性斑点病(Pseudomonas syringae pv.lachrymans)和蕃茄青枯病(Pseudomonas solanacearum)，由黄单胞菌引起的病害，如甘蓝黑腐病(Xanthomonas campestris)、稻白叶枯病(Xanthomonas oryzae)、柑桔溃疡病(Xanthomonas citri)和欧文氏菌引起的病害，如甘蓝软腐病(Erwinia carotovora)；和病毒性病害，例如烟草花叶病毒病(Tobocco mosaic virus)。所述的化合物是对(特别是)稻瘟病有高的防治活性的植物病害防治剂且对稻无药害。
含有本发明N-(3-氯-4-甲基苯基)-4-甲基-1，2，3-噻二唑-5-羧酰胺作为活性成分的农业与园艺病害防治剂在防治上面例举的损害水稻、旱田作物、果树、蔬菜、其它作物、花卉和观赏植物等的病害上非常有效。因此，本发明农业与园艺病害防治剂的所需效果可以通过在病害预期要发生的季节、在病害出现之前或在确定其已经发生时，将本发明病害防治剂施用于水稻田的水、果树的茎叶、蔬菜、其它作物、花卉、观赏植物和土壤等而获得。
通常，本发明的农业与园艺病害防治剂在根据农药剂型领域的普通方法制备成常规使用剂型之后使用。
即，本发明的N-(3-氯-4-甲基苯基)-4-甲基-1，2，3-噻二唑-5-羧酰胺和任选的辅助剂与适合的惰性载体以适合的比例掺合，通过溶解、分散、悬浮、混合、浸渍、吸附或粘合，制备成适合的制剂形式如悬浮剂、乳油、可溶性浓缩物、可湿性粉剂、粒剂、粉剂或片剂。
在本发明中使用的惰性载体可以是固体或液体。作为固体载体，可以例举大豆粉、谷粉、木粉、树皮粉、锯木屑、粉碎的烟茎、粉碎的胡桃壳、糠、纤维素粉、植物的提取残渣、粉状合成聚合物或树脂、陶土类(例如，高岭土、膨润土和酸性陶土)、滑石类(例如，滑石和叶蜡石)、硅石粉或片(例如，硅藻土、硅沙、云母和白碳黑，即，合成高分散性硅酸，也称为细分散的水合二氧化硅或水合硅酸，一些含有硅酸钙作为主要组分的商品化产品)、活性炭、硫磺粉、浮石粉、煅烧的硅藻土、碎砖、烟灰、沙、碳酸钙粉末、磷酸钙粉末和其它无机或矿物质粉末、化学肥料(例如硫酸铵、磷酸铵、硝酸铵、尿素和氯化铵)和堆肥。这些载体可以单独或组合使用。
液体载体是其本身具有溶解性或本身无溶解性但借助于助剂能够分散活性成分的液体载体。下列是液体载体的典型实例且可以单独或组合使用：水；醇类如甲醇、乙醇、异丙醇、丁醇和乙二醇；酮类如丙酮、甲乙酮、甲基异丁酮、二异丁基酮和环己酮；醚类如***、二噁烷、溶纤剂、二丙基醚和四氢呋喃；脂族烃如煤油和矿物油；芳族烃如苯、甲苯、二甲苯、溶剂石脑油和烷基萘；卤代烃类如二氯乙烷、氯仿、四氯化碳和氯苯；酯类如乙酸乙酯、邻苯二甲酸二异丙酯、邻苯二甲酸二丁基酯和邻苯二甲酸二辛基酯；酰胺类如二甲基甲酰胺、二乙基甲酰胺和二甲基乙酰胺；腈类如乙腈；和二甲亚砜。
下列是典型的助剂的实例，它们的使用取决于不同的目的且可单独使用或在某些情况下组合使用，或根本无需使用。
为乳化、分散、溶解和/或润湿活性成分，可以使用表面活性剂。作为表面活性剂，可以例举聚氧乙烯烷基醚、聚氧乙烯烷基芳基醚、聚氧乙烯高级脂肪酸酯、聚氧乙烯树脂酸酯、聚氧乙烯失水山梨糖醇单月桂酸酯、聚氧乙烯失水山梨糖醇单油酸酯、烷芳基磺酸盐、萘磺酸缩合产物、木素磺酸和高级醇的硫酸酯。
再者，为了活性成分分散液的稳定、粘合或粘结，可以使用助剂如酪蛋白、明胶、淀粉、甲基纤维素、羧甲基纤维素、***胶、聚乙烯醇类、松节油、糠油、膨润土和木素磺酸盐。
为改善固体产物的流动性，可以使用助剂如蜡、硬脂酸盐和烷基磷酸酯。
助剂如萘磺酸缩合产物和磷酸的缩聚物可以用作分散产物的胶溶剂。
也可以使用助剂如硅油作为消泡剂。
活性成分的含量可以按需要变化。在粉剂或粒剂中，其适合的含量是按重量计0.01到50％。在乳油或可湿性粉剂中，它可以是按重量计0.01到50％。
本发明的植物病害防治剂以下列方式防治各种病害。即，它可以在病害预期发生的作物上，或在不希望病害发生的位点，以其原样或在用水等适合地稀释或悬浮后，以防治病害的有效量施用。例如，为防治水稻病害，所述的病害防治剂可以通过例如下列方法施用：浸入施用于水稻田；在各种施用时间如在插秧期、转绿期和在苗床土壤混合至土壤覆盖的时期施用于育秧箱；漫灌稻田的直播的种子拌种；或种子消毒。为防治大麦、小麦、燕麦、黑麦、蔬菜等的病害，所述的植物病害防治剂不仅可以喷施于茎叶，而且也可以用此病害防治剂作种子处理，或通过将其施用于土壤而经根吸收病害防治剂。
本发明植物病害防治剂的施用剂量取决于各种因素，例如目的、意欲防治的病害、植物的生长期、病害发生的趋势、天气、环境条件、制剂形式、施用方法、施用位点和施用时间。取决于不同的目的，可以在每10公亩0.1克到10千克活性成分的范围内适当地选择。
本发明植物病害防治剂可以与其它农业与园艺病害防治剂混合，以扩大可防治病害的防治谱和有效施用可能的时间段或降低剂量。
实施例
下文描述的实施例1是制备本发明化合物方法的实施例。
实施例1
N-(3-氯-4-甲基苯基)-4-甲基-1，2，3-噻二唑-5-羧酰胺的制备
在150毫升四氢呋喃中溶解17克(0.12摩尔)的3-氯-4-甲基苯胺，接着在冰浴下用大约30分钟向其中滴加入20克(0.12摩尔)4-甲基-1，2，3-噻二唑-5-甲酰氯。之后在冰浴下用大约30分钟向其中滴加入19克(0.19摩尔)三乙胺。在滴加完毕后，反应在室温下搅拌2小时。反应完毕后，向含有所需化合物的反应溶液中加入饱和氯化钠水溶液，并将所需化合物用乙酸乙酯萃取。有机层依次用稀盐酸、饱和碳酸氢钠水溶液和饱和氯化钠水溶液洗涤，经无水硫酸钠干燥，过滤，之后减压浓缩，由此获得的33克粗制晶体用己烷-异丙醇重结晶，获得29克所需化合物。
物理性质：熔点114℃。
本发明的典型制剂实施例和试验实施例描述如下，但它们不应理解为限制本发明的范围。
制剂实施例1
本发明化合物 50份
二甲苯 40份
聚氧乙烯壬基苯基醚和 10份
烷基苯磺酸钙的混合物
通过将上述成分均一混合，进行溶解，制备成乳油。
制剂实施例2
本发明化合物 3份
粘土粉末 82份
硅藻土粉 15份
通过将上述成分均一混合并研碎，制备成粉剂。
制剂实施例3
本发明化合物 5份
膨润土和陶土的混合粉末 90份
木素磺酸钙 5份
通过将上述成分均一混合，并将所得的混合物与适量的水一起捏合，接着造粒并干燥，制备成粒剂。
制剂实施例4
本发明化合物 20份
高岭土和合成高分散硅酸 75份
的混合物
聚氧乙烯壬基苯基醚和 5份
烷基苯磺酸钙的混合物
通过将上述成分均一混合，制备成可湿性粉剂。
试验实施例1
淹灌施用对稻瘟病的防治效果
制备含有本发明化合物作为活性成分的可湿性粉剂和含有各参考化合物作为活性成分的可湿性粉剂。将在1/10000公亩盆中栽培的6叶期稻株(栽培品种：Kinnanpu)用每一种可湿性粉剂进行淹灌施用，施用剂量为每10公亩预定剂量活性成分。在温室中放置1周后，将稻株通过用稻梨孢(pyricularia oryzae)的孢子悬浮液喷雾来进行接种。接种后，让植株在20℃和高湿度下放置7天，以充分诱发病害。之后，计数每片叶上的病斑，之后将其与未处理小区叶片上的相比，计算出防治效力。未处理小区中的病斑数是每叶19个。
作为参考化合物，使用描述于JP-A-8-325110中描述的化合物。
A：N-苯基-4-甲基-1，2，3-噻二唑-5-羧酰胺，
B：N-(3-氯苯基)-4-甲基-1，2，3-噻二唑-5-羧酰胺，
C：N-(4-甲基苯基)-4-甲基-1，2，3-噻二唑-5-羧酰胺，
D：N-(3，4-二氯苯基)-4-甲基-1，2，3-噻二唑-5-羧酰胺，
E：N-(3，4-二甲基苯基)-4-甲基-1，2，3-噻二唑-5-羧酰胺。
获得的结果示于表1中。
表1
| 试验化合物 | 剂量(g.ai/10a) | 防治效力(％) | |
| 本发明小区 | 本发明化合物 | 101 | 9890 |
| 参考小区 | A | 101 | 770 |
| B | 101 | 8030 | |
| C | 101 | 9075 | |
| D | 101 | 8557 | |
| E | 101 | 7050 |
如表1中所示，本发明化合物在10克和1克活性成分/10公亩的剂量下对稻瘟病的防治非常有效。另一方面，参考化合物A至E在200克活性成分/10公亩的剂量下，在JP-A-8-325110第49页左栏第24行到右栏第34中的描述中定为A级。但如表1中所示，在10克至1克的剂量下，其效果降低，参考化合物A至E在效果上显著劣于本发明化合物。
试验实施例2
稻瘟病大田防治效果及药害试验
在苗床中培育的稻株(栽培品种：Kinuhikari)用根据制剂实施例制备的预定量的粒剂在插秧当日处理。施用的粒剂量为50克每块苗床。处理后，用少量水喷洒稻株，并用常规插秧机***正常的稻田中。
插秧在五月初进行，在用粒剂处理50天后对药效和药害进行调查。对照效果用与试验实施例1中相同的方式进行确定。药害通过将每株植物的茎数与未处理小区的相比较来确定，并示出前者除以后者得的百分率。在未处理小区中，每株的茎数为21.4，病斑数为每株41.8个。
获得的结果示于表2中。
表2
| 试验化合物 | 茎数(％) | 防治效力(％) | |
| 本发明小区 | 本发明化合物 | 101 | 98 |
| 参考小区 | B | 72 | 74 |
| C | 82 | 80 | |
| D | 90 | 72 |
如表2中，本发明化合物没有药害且表现出优异的防治效果。另一方面，参考化合物B、C和D在防治效果上明显要比本发明化合物差，且有药害如减少茎数。因此，它们最终对产量有严重的影响。
试验实施例3
喷雾施用对黄瓜细菌性斑点病(cucumber bacterial spot)的防治效果
含有本发明化合物作为活性成分的可湿性粉剂和含有各参考化合物作为活性成分的可湿性粉剂用水稀释。将在9厘米直径的盆中栽培的1.5叶期黄瓜植株(栽培品种：Yotsuba)用150升/10公亩的量喷雾。将黄瓜植株在温室中培育8天后，将其通过用黄瓜霜霉病菌(Pseudoperonospora cubensis)的游动孢子喷雾来进行接种(接种时，黄瓜植株处于3叶期)。接种后，让植株在20℃和高湿度下放置7天，以充分诱发病害。之后，计数各植株的第一至第三片叶上的病斑，之后将其与未处理小区叶片上的相比，计算出防治效力。未处理小区中的病斑数是每叶4个。
获得的结果示于表3中。
表3
| 试验化合物 | 剂量(ppm) | 防治效力(％) | |
| 本发明小区 | 本发明化合物 | 20020 | 9665 |
| 参考小区 | A | 20020 | 460 |
| C | 20020 | 500 |
如表3中所示，本发明化合物在200ppm的浓度下，即使是在用本发明化合物处理8天后用真菌接种时，仍保持显著的防治效果。
试验实施例4
小麦白粉病大田防治效果
含有本发明化合物作为活性成分的可湿性粉剂和含有参考化合物作为活性成分的可湿性粉剂用水稀释。各稀释液在五月初以100升/10公亩的量对九月下旬播种的小麦喷雾一次(栽培品种：Chihoku)。在参考药剂小区中，在五月中旬用醚菌酯(俗名)喷雾一次，用硫磺在五月中旬和六月上旬各喷雾一次。测定每一子叶上的病斑面积百分率，之后将其与未处理小区中的相比，计算出防治效力。未处理小区中的病斑面积百分率为每叶17％。
结果示于表4中。
| 试验化合物 | 剂量(ppm) | 防治效力(％) | |
| 本发明小区 | 本发明化合物 | 400 | 100 |
| 参考小区 | C | 400 | 24 |
| 参考药剂小区 | 醚菌酯硫磺 | 1001300 | 5250 |
如表4中所示，当以400ppm的浓度施用一次时，本发明化合物对小麦白粉病的防治效果优于用醚菌酯施用一次和用硫磺施用二次的效果以及优于参考化合物C。
Claims (3)
1.N-(3-氯-4-甲基苯基)-4-甲基-1，2，3-噻二唑-5-羧酰胺。
2.一种植物病害防治剂，其特征在于含有N-(3-氯-4-甲基苯基)-4-甲基-1，2，3-噻二唑-5-羧酰胺作为活性成分。
3.一种防治植物病害的方法，其特征在于用有效量的含有N-(3-氯-4-甲基苯基)-4-甲基-1，2，3-噻二唑-5-羧酰胺作为活性成分的植物病害防治剂处理意欲保护的作物。
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP316427/1997 | 1997-10-31 | ||
| JP31642797 | 1997-10-31 |
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| CN1278254A true CN1278254A (zh) | 2000-12-27 |
| CN1098845C CN1098845C (zh) | 2003-01-15 |
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| EP (1) | EP1031567B1 (zh) |
| KR (1) | KR100367325B1 (zh) |
| CN (1) | CN1098845C (zh) |
| AU (1) | AU730694B2 (zh) |
| BG (1) | BG64312B1 (zh) |
| CA (1) | CA2307598C (zh) |
| DE (1) | DE69813004T2 (zh) |
| DK (1) | DK1031567T3 (zh) |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101091490B (zh) * | 2007-01-12 | 2010-11-03 | 南开大学 | 杂环杀菌剂及其组合物 |
| CN103416427A (zh) * | 2012-05-23 | 2013-12-04 | 陕西韦尔奇作物保护有限公司 | 一种含噻酰菌胺的杀菌组合物 |
| CN104996436A (zh) * | 2015-06-28 | 2015-10-28 | 安徽省农业科学院植物保护与农产品质量安全研究所 | 一种含氟啶胺和噻酰菌胺的杀菌组合物 |
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| EP1175834A4 (en) * | 1999-04-30 | 2006-03-01 | Nihon Nohyaku Co Ltd | METHOD OF USING BACTERICIDE COMPOSITION |
| CN102524269B (zh) * | 2012-01-17 | 2013-10-30 | 利尔化学股份有限公司 | 杀菌组合物、农药及其应用 |
| BR112014017552A8 (pt) * | 2012-01-21 | 2017-07-04 | Bayer Ip Gmbh | utilização de indutores de defesa em hospedeiros para controlar organismos basterianos prejudiciais em plantas úteis |
| CN105557745A (zh) * | 2015-12-28 | 2016-05-11 | 南京华洲药业有限公司 | 一种含硅噻菌胺和噻酰菌胺的杀菌组合物及其应用 |
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| DE2728523C2 (de) * | 1977-06-23 | 1986-02-27 | Schering AG, 1000 Berlin und 4709 Bergkamen | 4-Methyl-1,2,3-thiadiazol-5-carbonsäure-(cyclohexylmethyl)-amid, Mittel mit herbizider und wachstumsregulatorischer Wirkung enthaltend diese Verbindung sowie Verfahren zu seiner Herstellung |
| DE3030736A1 (de) * | 1980-08-14 | 1982-03-25 | Basf Ag, 6700 Ludwigshafen | N-disubstituierte anilinderivate, ihre herstellung, ihre verwendung als mikrobizide und mittel dafuer |
| MY113237A (en) * | 1995-03-31 | 2001-12-31 | Nihon Nohyaku Co Ltd | An agricultural and horticultural disease controller and a method for controlling the diseases |
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1998
- 1998-10-30 DK DK98950461T patent/DK1031567T3/da active
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- 1998-10-30 EP EP98950461A patent/EP1031567B1/en not_active Expired - Lifetime
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101091490B (zh) * | 2007-01-12 | 2010-11-03 | 南开大学 | 杂环杀菌剂及其组合物 |
| CN103416427A (zh) * | 2012-05-23 | 2013-12-04 | 陕西韦尔奇作物保护有限公司 | 一种含噻酰菌胺的杀菌组合物 |
| CN103416427B (zh) * | 2012-05-23 | 2017-05-31 | 林建春 | 一种含噻酰菌胺的杀菌组合物 |
| CN104996436A (zh) * | 2015-06-28 | 2015-10-28 | 安徽省农业科学院植物保护与农产品质量安全研究所 | 一种含氟啶胺和噻酰菌胺的杀菌组合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999023084A1 (fr) | 1999-05-14 |
| KR20010031199A (ko) | 2001-04-16 |
| BG64312B1 (bg) | 2004-09-30 |
| ES2195405T3 (es) | 2003-12-01 |
| DE69813004T2 (de) | 2003-09-25 |
| PL340334A1 (en) | 2001-01-29 |
| DE69813004D1 (de) | 2003-05-08 |
| TW474788B (en) | 2002-02-01 |
| AU730694B2 (en) | 2001-03-15 |
| CN1098845C (zh) | 2003-01-15 |
| EP1031567B1 (en) | 2003-04-02 |
| KR100367325B1 (ko) | 2003-01-09 |
| HUP0100608A3 (en) | 2002-11-28 |
| EP1031567A1 (en) | 2000-08-30 |
| HUP0100608A2 (hu) | 2001-06-28 |
| ID24100A (id) | 2000-07-06 |
| BG104339A (en) | 2001-08-31 |
| CA2307598A1 (en) | 1999-05-14 |
| AU9650898A (en) | 1999-05-24 |
| CA2307598C (en) | 2004-03-30 |
| EP1031567A4 (en) | 2002-07-03 |
| DK1031567T3 (da) | 2003-04-22 |
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