CN1214015C - 2-[2-(1-氯环丙基)-3-(2-氯苯基)基-2-羟丙基]-2,4-二氢-[1,2,4]-三唑-3-硫酮的(-)对映体 - Google Patents
2-[2-(1-氯环丙基)-3-(2-氯苯基)基-2-羟丙基]-2,4-二氢-[1,2,4]-三唑-3-硫酮的(-)对映体 Download PDFInfo
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- CN1214015C CN1214015C CNB00806489XA CN00806489A CN1214015C CN 1214015 C CN1214015 C CN 1214015C CN B00806489X A CNB00806489X A CN B00806489XA CN 00806489 A CN00806489 A CN 00806489A CN 1214015 C CN1214015 C CN 1214015C
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- Prior art keywords
- chloro
- phenyl
- methyl
- dihydro
- triazole
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- Expired - Lifetime
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Abstract
本发明涉及新的式(I)的2-[2-(1-氯环丙基)-3-(2-氯苯基)-2-羟基丙基]-2,4-二氢-[1,2,4]-三唑-3-硫酮的(-)对映体、制备该新活性成分的方法及该新活性成分作为杀微生物剂用于保护植物和材料的用途。
Description
本发明涉及新的2-[2-(1-氯环丙基)-3-(2-氯苯基)-2-羟基丙基]-2,4-二氢-[1,2,4]-三唑-3-硫酮的(-)对映体、其制备方法及其作为杀微生物剂的用途。
已知2-[2-(1-氯环丙基)-3-(2-氯苯基)-2-羟基丙基]-2,4-二氢-[1,2,4]-三唑-3-硫酮的外消旋体具有杀真菌性能(参见WO96-16048)。该物质的活性是好的;但是,在非常低的施用率时它有时并不令人满意。
因此,本发明提供新的下式的2-[2-(1-氯环丙基)-3-(2-氯苯基)-2-羟基丙基]-2,4-二氢-[1,2,4]-三唑-3-硫酮的(-)对映体,
在此,(-)对映体在每种情况下都应理解为使钠-D-线的线性极化光的振动平面向左旋转的对映体。
此外,现已发现,如下可以获得式(I)的2-[2-(1-氯环丙基)-3-(2-氯苯基)-2-羟基丙基]-2,4-二氢-[1,2,4]-三唑-3-硫酮的(-)对映体:
a)在基于光学活性单体N-甲基丙烯酰基-L-亮氨酸-3-(2,4-二甲基戊基)酰胺的手性固定的硅胶相上用乙酸乙酯作为移动相在20-25℃的温度下对式(Ia)的2-[2-(1-氯环丙基)-3-(2-氯苯基)-2-羟基丙基]-2,4-二氢-[1,2,4]-三唑-3-硫酮的外消旋体进行色谱层析,
b)减压下浓缩洗脱液,和
c)用甲苯对所得产物进行重结晶。
最后,现已发现,新的式(I)的2-[2-(1-氯环丙基)-3-(2-氯苯基)-2-羟基丙基]-2,4-二氢-[1,2,4]-三唑-3-硫酮的(-)对映体具有非常好的杀微生物性能并且可用于在作物保护和材料保护中防治不希望的微生物如真菌。
令人惊奇的是,本发明的式(I)的2-[2-(1-氯环丙基)-3-(2-氯苯基)-2-羟基丙基]-2,4-二氢-[1,2,4]-三唑-3-硫酮的(-)对映体比相应的(+)对映体和相应的外消旋体具有好得多的杀真菌活性,后者作为具有杀真菌性能的高度有效的活性物质是已知的。
本发明的(-)对映体的全部或部分可以以下式“硫羰”的形式存在,
或者以下式互变异构“巯基”形式存在,
为简单起见,在每种情况下只示出“硫羰”形式。
在式(I)和式(Ib)中,不对称取代的碳原子在每种情况下都用(*)标记。
对于进行本发明方法用作原料所需要的式(Ia)的2-[2-(1-氯环丙基)-3-(2-氯苯基)-2-羟基丙基]-2,4-二氢-[1,2,4]-三唑-3-硫酮的外消旋体是已知的(参见WO96-16048)。
当进行本发明的方法时,使用制备色谱方法、优选高效液相色谱(HPLC)方法。用于该目的的分离原料是已知的(参见EP-A-0 397917)。
在洗脱液中的物质含量通过光度计检测测定。对所收集的洗脱液部分进行对映异构纯度分析。合并所有的含有同一种对映体的洗脱部分并减压浓缩。然后将所得产物用甲苯重结晶。
先洗脱下来的产物是本发明的(-)对映体。从随后洗脱下来的部分可以分离相应的(+)对映体。
本发明活性化合物具有强的杀微生物作用,可用来在作物保护和材料保护中防治不期望的微生物,例如真菌和细菌。
作物保护中的杀真菌剂被用来防治根肿菌(Plasmodiophoromycetes),卵孢真菌(Oomycetes),壶菌(Chytridiomycetes),接合菌亚纲(Zygomycetes),子囊菌(Ascomycetes),担子菌纲(Basidiomycetes)和半知菌纲(Deutermycetes)。
杀细菌剂在作物保护中可被用来防治假单胞菌科(Pseudomonadaceae)、根瘤菌科(Rhizobiaceae)、肠杆菌科(Enterobacteriaceae)、棒状杆菌科(Corynebacteriaceae)和链霉菌科(Streptomycetaceae)。
作为例子,可以提到上述属名下的真菌病和细菌病的一些病因微生物,但是不受此限制:
黄单孢菌属种类(Xanthomonas),例如稻黄单孢菌(Xanthomonascampestris pv.oryzae);
假单孢菌属种类(Pseudomonas),例如黄瓜角斑病假单孢菌(Pseudomonas syringae pv.lachrymans);
欧文氏杆菌属种类(Erwinia),例如解淀粉欧文氏杆菌(Erwiniaamylovora);
腐霉属种类(Pythium),例如终极腐霉(Pythium ultimum);
疫霉属种类(Phytophthora),例如蔓延疫霉(Phytophthorainfestans);
假霜霉属种类(Pseudoperonospora),例如律草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(Pseudoperonosporacubensis);
单轴霉属种类(Plasmopara),例如葡萄生单轴霉(Plasmoparaviticola);
Bremia种类,例如Bremia lactucae;
霜霉属种类(Peronospora),例如豌豆霜霉(Peronospora pisi)或芸苔霜霉(Peronospora brassicae);
白粉菌属种类(Erysiphe),例如禾白粉菌(Erysiphe graminis);
单丝壳菌属种类(Sphaerotheca),例如苍耳单丝壳菌(Sphaerotheca fuliginea);
柄球菌属种类(Podosphaera),例如苹果白粉病柄球菌(Podosphaera leucotricha);
黑星菌属种类(Venturia),例如苹果黑星菌(Venturiainaequalis);
核腔菌属种类(Pyrenophora),例如圆核腔菌(Pyrenophorateres)或麦类核腔菌(Pyrenophora graminea)
(分生孢子形式:长蠕孢(Drechslera),同义词:长蠕孢(Helminthosporium)):
旋孢菌属种类(Cochli obolus),例如禾旋孢菌(Cochliobolussativus)
(分生孢子形式:长蠕孢(Drechslera),同义词:长蠕孢(Helminthosporium));
单胞锈菌属种类(Uromyces),例如疣顶单胞锈菌(Uromycesappendi culatus);
柄锈菌属种类(Puccinia),例如隐匿柄锈菌(Pucciniarecondita);
Sclerotinia种类,例如Sclerotinia sclerotiorum;
腥黑粉菌属种类(Tilletia),例如小麦网腥黑粉菌(Tilletiacaries);
黑粉菌属种类(Ustilago),例如裸黑粉菌(Ustilago nuda)或燕麦黑粉菌(Ustilago avenae);
薄膜革菌属种类(Pellicularia),例如佐佐木氏薄膜革菌(Pellicularia sasakii);
Pyricularia种类,例如Pyricularia oryzae;
镰孢属种类(Fusarium),例如大刀镰孢(Fusarium culmorum);
葡萄孢属种类(Botrytis),例如灰色葡萄孢(Botrytiscinerea);
壳针孢属种类(Septoria),例如颖枯壳针孢(Septorianodorum);
小球腔菌属种类(Leptosphaeria),例如颖枯小球腔菌(Leptosphaeria nodorum);
尾孢属种类(Cercospora),例如Cercospora canescens;
链格孢属种类(Alternaria),例如甘蓝黑斑病链格孢(Alternaria brassicae);
假尾孢属种类(Pseudocercosporella),例如Pseudocercosporellaherpotrichoides。
植物对在防治植物病害所需要的浓度时的活性化合物的好的耐受性允许处理植物的地上部分,植物繁殖根株和种子,和处理土壤。
本发明活性化合物可以用来特别成功地防治水果和蔬菜生长以及葡萄栽培中的病害,例如,防治粉状霉病真菌如单丝壳属(Sphaerotheca)、钩丝壳属(Uncinula),防治白粉菌属(Erysiphe)种类和叶斑如黑星菌属(Venturia)和链格孢属(Alternaria)种类。也能非常成功地防治谷类病害如白粉菌属(Erysiphe)、Leptosphaeria或Pyrenophora种类以及稻病害如Pyricularia种类。
本发明的活性化合物还适于增加作物产量。此外,它具有降低的毒性并被作物很好地耐受。
在材料保护中,本发明物质可被用来保护工业材料不受不期望微生物的侵蚀和破坏。
本说明书中工业材料一词是指制备出来用于工业应用的无生命材料。例如,待受本发明活性化合物保护不受微生物改变或破坏的工业材料可以是粘合剂,胶料,纸张和纸板,纺织品,皮革,木材,涂料,和塑料制品,冷却润滑剂和其它能被微生物侵蚀或分解的材料。要保护的材料的含义也包括生产工厂的部分,例如冷却水循环,其可能受微生物再生的不利影响。本发明说明书中优选的工业材料是粘合剂,胶料,纸张和纸板,皮革,木材,涂料,冷却润滑剂和导热液,特别优选木材。
能导致工业材料中降解或改变的微生物的例子是细菌,真菌,酵母,藻和粘液生物。本发明活性化合物优选作用于真菌,特别是霉菌,使木材退色和使木材遭破坏的真菌(担子菌纲(Basidiomycetes)),以及也作用于杀粘液生物和藻。
作为举例,可以提到下面属种:
链格孢属(Alternaria),例如纤细链格孢(Alternaria tenuis),
曲霉属(Aspergillus),例如黑色曲霉(Aspergillus niger),
毛壳霉属(Chaetomium),例如球毛壳霉(Chaetomium globosum),
粉孢革菌属(Coniophora),例如单纯粉孢革菌(Coniophorapuetana),
香菇属(Lentinus),例如虎皮香菇(Lentinus tigrinus),
青霉属(Penicillium),例如灰绿青霉(Penicillium glaucum),
多孔菌属(Polyorus),例如变色多孔菌(Polyorus versicolor),
短柄霉属(Aureobasidium),例如出芽短柄霉(Aureobasidiumpullulans),
Sclerophoma,例如Sclerophoma pityophila,
木霉属(Trichoderma),例如绿色木霉(Trichoderma viride),
埃希氏杆菌属(Escherichia),例如大肠埃希氏杆菌(Escherichia coli),
假单孢菌属(Pseudomonas),例如铜绿假单孢菌(Pseudomonasaeruginosa),
葡萄球菌属(Staphyl ococcus),例如金黄色葡萄球菌(Staphylococcus aureus)。
活性化合物可以配制成常规制剂,例如溶液、乳液、悬浮液、粉剂、泡沫剂、糊剂、颗粒剂、气雾剂,包裹在聚合物中和在用于种子的包被组合物中的细微胶囊,以及ULV冷雾和热雾制剂。
这些型剂可以用已知的方式制备,例如,将活性化合物与扩充剂即液体溶剂,加压液化气体和/或固体载体混合,任选地使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。如果使用的扩充剂是水,则也可以用例如有机溶剂作助溶剂。合适的液体溶剂主要有:芳香族化合物,如二甲苯,甲苯或烷基萘,氯代芳香族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如矿物油馏份,醇类,如丁醇或乙二醇以及其醚和酯,酮类,如丙酮、甲乙酮、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亚砜,以及水。液化气体扩充剂或载体是指常温常压下是气体的液体,例如气雾抛射剂,例如卤代烃及丁烷,丙烷,氮和二氧化碳;作为固体载体适合的有例如:磨碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐。作为用于颗粒剂的固体载体适合的有:例如压碎和破碎的天然矿物质如方解石、大理石、浮石、海泡石和白云石,以及有机和无机粉的合成颗粒,和如下有机物的颗粒:例如锯木屑、椰壳、玉米穗轴和烟茎;作为乳化剂和/或起泡剂适合的有: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;作为分散剂适合的有:例如,木素亚硫酸盐废液和甲基纤维素。
制剂中,可以使用增粘剂如羧甲基纤维素、天然和合成的粉状、颗粒或乳胶形式的聚合物,如阿拉伯胶、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。其它添加剂可以是矿物油和植物油。
也可能使用着色剂,如元机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
一般情况下,制剂含有0.1-95%重量的活性化合物,优选0.5-90%。
本发明活性化合物也可以以本身或者以它们的制剂作为与其它已知的杀真菌剂,杀细菌剂,杀螨剂、杀线虫剂或杀昆虫剂的混合物使用,例如以扩大作用范围或者防止抗性产生。在很多情况下这样会导致增效效果,即混合物的活性超过了各个组分的活性。
作为混合组分,下列化合物是一些例子:
杀真菌剂:
aldimorph,氨丙磷酸,氨丙磷酸钾盐,andoprim,敌菌灵,戊环唑,azoxystrobin,
苯霜灵,邻碘酰苯胺,苯菌灵,benzamacril,benzamacryl-isobutyl,双丙氨酰磷,乐杀螨,联苯,双苯三唑醇,灭瘟素,糠菌唑,乙嘧酚磺酸酯,丁赛特,
石硫合剂,capsimycin,敌菌丹,克菌丹,多菌灵,萎锈灵,carvone,灭螨猛,灭瘟唑,chlorfenazole,地茂散,氯化苦,百菌消,乙菌利,clozylacon,代森盐,霜尿氰,环唑醇,cyprodinil,酯菌胺,
debacarb,双氯酚,苄氯三唑醇,diclofluanid,哒菌清,氯硝胺,乙霉威,噁醚唑,二甲嘧吩,烯酸吗啉,烯唑醇(diniconazole),烯唑醇(diniconazole-M),二硝巴豆酸酯,二苯胺,吡菌硫,灭菌磷,二噻农,十二环吗啉,多果定,联氨噁唑酮,
克瘟散,epoxiconazole,乙环唑,乙嘧酚,土菌灵,
famoxadon,咪菌腈,氯苯嘧啶醇,fenbuconazole,甲呋酰苯胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,三苯基醋酸锡,三苯基氢氧化锡,福美铁,嘧菌腙,氟啶胺,flumetover,氟氯菌核利,fluquinconazole,调嘧醇,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,乙磷钠,四氯苯酞,麦穗宁,呋霜灵,furametpyr,二甲呋酰苯胺,呋菌唑,呋醚唑,拌种胺,
谷种定,
六氯苯,己唑醇,噁霉灵,
抑霉唑,酰胺唑,双胍辛醋酸盐(iminoctadine,iminoctadinealbesilate,iminoctadine triacetate),iodocarb,ipconazole,异稻瘟净(IBP),异菌脲,irumamycin,稻瘟灵,isovaledione,
春雷霉素,kresoxim-methyl,铜制剂,例如:氢氧化铜,环烷酸铜,氯氧化铜,硫酸铜,氧化铜,8-羟基喹啉铜和波尔多液,
代森锰铜,代森锰,代森锰锌,meferimzone,嘧菌胺,灭锈胺,甲霜灵,metconazole,磺菌威,呋菌胺,代森联,氯苯咯菌胺,噻菌胺,米多霉素,腈菌唑,甲菌利,
二甲基二硫氨基甲酸镍,nitrothal-isopropyl,氟苯嘧啶醇,
甲呋酰胺,噁霜灵,oxamocarb,喹菌酮,氧化萎锈灵,oxyfenthiin,
稻瘟酯,戊菌唑,戊菌隆,稻瘟磷,四氯苯酞,多马霉素,病花灵,聚氨基甲酸酯,多氧霉素,烯病异噻唑,味鲜安,腐霉利,丙酰胺,propanosine-sodium,环丙唑,丙森锌,吡嘧磷,啶斑肟,pyrimethanil,咯喹酮,氯吡呋醚,
quinconazole,五氯硝基苯(PCNB),quinoxyfen,
硫和硫制剂,
戊唑醇,叶枯酞,四氯硝基苯,调环烯,氟嘧唑,噻菌灵,噻菌腈,thifluzamide,甲基硫菌灵,福美双,tioxymid,甲基立枯磷,甲基氟磺胺,三唑酮,三唑醇,triazbutil,唑菌嗪,杨菌胺,三环唑,十三吗啉,氟菌唑,嗪氨灵,triticonazole,
烯效唑,
稻纹散,乙烯菌核利,烯霜苄唑,
zarilamide,代森锌,福美锌,还有
Dagger G,
OK-8705,
OK-8801,
α-(1,1-二甲基乙基)-β-(2-苯氧基乙基)-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-氟-b-丙基-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-甲氧基-a-甲基-1H-1,2,4-三唑-1-乙醇,
α-(5-甲基-1,3-二噁烷-5-基)-β-[[4-(三氟甲基)-苯基]-亚甲基]-1H-1,2,4-三唑-1-乙醇,
(5RS,6RS)-6-羟基-2,2,7,7-四甲基-5-(1H-1,2,4-三唑-1-基)-3-辛酮,
(E)-a-(甲氧基亚氨基)-N-甲基-2-苯氧基-苯基乙酰胺,
{2-甲基-1-[[[1-(4-甲基苯基)-乙基]-氨基]-羰基]-丙基)-氨基甲酸异丙酯,
1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)-乙酮O-(苯基甲基)-肟,
1-(2-甲基-1-萘基)-1H-吡咯-2,5-二酮,
1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯烷二酮,
1-[(二碘代甲基)-磺酰基]-4-甲基-苯,
1-[[2-(2,4-二氯苯基)-1,3-二氧戊环-2-基]-甲基]-1H-咪唑,
1-[[2-(4-氯苯基)-3-苯基环氧乙烷基]-甲基]-1H-1,2,4-三唑,
1-[1-[2-[(2,4-二氯苯基)-甲氧基]-苯基]-乙烯基]-1H-咪唑,
1-甲基-5-壬基-2-(苯基甲基)-3-吡咯烷醇,
2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟-甲基-1,3-噻唑-5-N-碳酰苯胺,
2,2-二氯-N-[1-(4-氯苯基)-乙基]-1-乙基-3-甲基-环丙烷甲酰胺,
2,6-二氯-5-(甲硫基)-4-嘧啶基-硫代氰酸酯,
2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺,
2,6-二氯-N-[[4-(三氟甲基)-苯基]-甲基]-苯甲酰胺,
2-(2,3,3-三碘代-2-丙烯基)-2H-四唑,
2-[(1-甲基乙基)磺酰基]-5-(三氯甲基)-1,3,4-噻二唑,
2-[[6-脱氧-4-O-(4-O-甲基-β-D-吡喃葡糖基)-α-D-吡喃葡糖基]-氨基]-4-甲氧基-1H-吡咯并[2,3-d]嘧啶-5-腈,
2-氨基丁烷,
2-溴-2-(溴代甲基)戊烷二腈,
2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺,
2-氯-N-(2,6-二甲基苯基)-N-(异硫代氰酰甲基)-乙酰胺,
2-苯基苯酚(OPP),
3,4-二氯-1-[4-(二氟甲氧基)-苯基]-1H-吡咯-2,5-二酮,
3,5-二氯-N-[氰基-[(1-甲基-2-丙炔基)-氧基]-甲基]-苯甲酰胺,
3-(1,1-二甲基丙基-1-氧代-1H-茚-2-腈),
3-[2-(4-氯苯基)-5-乙氧基-3-异噁唑啉基]-吡啶,
4-氯-2-氰基-N,N-二甲基-5-(4-甲基苯基)-1H-咪唑-1-磺酰胺,
4-甲基-四唑并[1,5-a]喹唑啉-5(4H)-酮,
8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二氧杂螺[4.5]癸烷-2-甲烷胺,
8-羟基喹啉硫酸盐,
9H-呫吨-2-[(苯基氨基)-羰基]-9-羧酸酰肼,
双-(1-甲基乙基)-3-甲基-4-[(3-甲基苯甲酰基)氧基]-2,5-硫代苯二羧酸酯,
顺-1-(4-氯代苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇,
顺-4-[3-[4-(1,1-二甲基丙基)-苯基-2-甲基丙基]-2,6-二甲基-吗啉]盐酸盐,
[(4-氯苯基)-偶氮]-氰基乙酸乙酯,
碳酸氢钾,
甲烷四硫醇钠盐,
1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯,
N-(2,6-二甲基苯基)-N-(5-异噁唑基羰基)-DL-丙氨酸甲酯,
N-(氯代乙酰基)-N-(2,6-二甲基苯基)-DL-丙氨酸甲酯,
N-(2,3-二氯-4-羟基苯基)-1-甲基-环己烷甲酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-呋喃基)-乙酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-噻吩基)-乙酰胺,
N-(2-氯-4-硝基苯基)-4-甲基-3-硝基-苯磺酰胺,
N-(4-环己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(4-己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(5-氯-2-甲基苯基)-2-甲氧基-N-(2-氧代-3-噁唑啉基)-乙酰胺,
N-(6-甲氧基)-3-吡啶基)-环丙烷甲酰胺,
N-[2,2,2-三氯-1-[(氯代乙酰基)-氨基]-乙基]-苯甲酰胺,
N-[3-氯代-4,5-双(2-丙炔基氧基)-苯基]-N’-甲氧基-甲烷亚氨酰胺,
N-甲酰基-N-羟基-DL-丙氨酸钠盐,
O,O-二乙基[2-(二丙基氨基)-2-氧代乙基]-乙基硫代氨基磷酸酯,
O-甲基S-苯基苯基丙基硫代氨基磷酸酯,
S-甲基1,2,3-苯并噻二唑-7-硫代甲酸酯,
螺[2H]-1-苯并吡喃-2,1’(3’H)-异苯并呋喃-3’-酮,
杀细菌剂:
溴硝醇,双氯酚,氯甲基吡啶,二甲基二硫氨基甲酸镍,春雷霉素,异噻唑酮,呋喃羧酸,oxytetracycline,烯异丙噻唑,链霉素,叶枯酞,硫酸铜和其它铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
齐墩螨素,乙酰甲胺磷,Acetamiprid,氟酯菊酯,棉铃威,涕灭威,氧涕灭威,甲体氯氰菊酯(Alpha-cypermethrin,Alphamethrin),双虫脒,avermectin,AZ60541,azadirachtin,甲基吡噁磷,azinphos-A,保棉磷,三唑锡,
日本甲虫芽孢杆菌(Bacillus popilliae),球形芽孢杆菌(Bacillus sphaericus),枯草芽孢杆菌(Bacillus subtilis),苏云金芽孢杆菌(Bacillus thuringiensis),Baculoviren,蚕白僵菌(Beauveria bassiana),纤细白僵菌(Beauveria tenella),噁虫威,丙硫克百威,杀虫磺,苯螨特,氟氯氰菊酯,Bifenazate,氟氯菊酯,Bioethanomethrin,生物氯菊酯,BPMC,Bromophos A,溴硫磷,合杀威,噻嗪酮,丁酮威,butylpyridaben,
硫线磷,甲萘威,克百威,三硫磷,丁硫百克威,杀螟丹,Chloethocarb Chlorethoxyfos,Chlorfenapyr,毒虫畏,定虫隆,氯甲硫磷,毒死蜱,甲基毒死蜱,Chlovaporthrin,顺式-苄呋菊酯,顺式氯菊酯,clocythrin,除线威,四螨嗪,杀螟腈,Cycloprene,乙氰菊酯,氟氯氰菊酯-β,cyhalothrin,三环锡,氯氰菊酯,灭蝇胺,
溴氰菊酯,内吸磷-M,内吸磷-S,甲基内吸磷,杀螨隆,二嗪磷,敌敌畏,除虫脲,乐果,甲基毒虫畏,diofenolan,乙拌磷,docusat-sodium,dofenapyn,
克瘟散,emamectin,烯炔菊酯,硫丹,entomopfthora spp.,高氰戊菊酯,乙硫苯威,乙硫磷,灭线磷,etofenprox,醚菊酯,乙嘧硫磷,
虫胺磷,喹螨醚,苯丁锡,杀螟硫磷,苯硫威,fenoxacrim,双氧威,氯氰菊酯,fenpyrad,fenpyrithrin,唑螨酯,氰戊菊酯,fipronil,氟定胺,fluazuron,flubrocythrinate,氟螨脲,氟氰戊菊酯,氟虫脲,Flutellzine,氟胺氰菊酯,地虫硫磷,丁苯硫磷,噻唑磷,fubfenprox,呋线威,
Granulosis viruses,
Halofenozide,HCH,庚烯磷,氟铃脲,噻螨酮,烯虫乙酯,
吡虫啉,氯唑磷,异丙胺磷,噁唑磷,ivermectin,
Nuclear polyhedrosis viruses,
氯氟氰菊酯,lufenuron,
马拉硫磷,灭蚜蜱,速灭磷,methamidophos,Metharhiziumanisopliae,Metharhizium flavoviride,蜗牛敌,虫螨畏,甲胺磷,杀扑磷,灭梭威,灭多威,速灭威,milbemectin,久效磷,
二溴磷,nitenpyram,Nithiazine,Novaluron,
氧乐果,杀线威,亚砜吸磷,
玫烟色拟青霉(Paecilomyces fumosoroseus),对硫磷-A,对硫磷-M,氯菊酯,稻丰散,甲拌磷,伏杀硫磷,亚胺硫磷,磷胺,辛硫磷,抗芽威,嘧啶磷-A,嘧啶磷-M,丙溴磷,猛杀威,残杀威,丙硫磷,发果,pymetrozine,吡唑硫磷,pyresmethrin,除虫菊酯,哒螨酮,Pyridathion,pyrimidifen,蚊蝇醚,
喹硫磷,
Ribavirin,
蔬果磷,sebufos,silafluofen,spinosad,治螟硫磷,甲丙硫磷,
氟胺氰菊酯,tebufenozid,tebufenpyrad,tebupirimiphos,伏草隆,七氟菊酯,双硫磷,特灭威,特丁磷,杀虫畏,theta-cypermethrin,thiamethoxam,thiapronil,thiatriphos,thiocyclam hydrogen oxalate,硫双威,久效磷,thuringiensin,二甲硫吸磷,虫线磷,四溴菊酯,苯噻螨,三唑磷,triazuron,trichlophenidine,敌百虫,杀虫隆,混灭威,
芽灭多,vaniliprole,verticillium lecanii,
YI5302,
zeta-cypermethrin,zolaprofos,
环丙烷羧酸(1R-顺式)-[5-(苯基甲基)-3-呋喃基]-甲基-3-[(二氢-2-氧代-3(2H)-亚呋喃基)-甲基]-2,2-二甲酯,
环丙烷羧酸(3-苯氧基苯基)-甲基-2,2,3,3-四甲酯,
1-[(2-氯-5-噻唑基)甲基]四氢-3,5-二甲基-N-硝基-1,3,5-三嗪-2(1H)-亚胺,
2-(2-氯-6-氟代苯基)-4-[4-(1,1-二甲基乙基)苯基]-4,5-二氢-噁唑,
2-(乙酰氧基)-3-十二烷基-1,4-萘二酮,
2-氯-N-[[[4-(1-苯基乙氧基)苯基]-氨基]-羰基]-苯甲酰基,
2-氯-N-[[[4-(2,2-二氯-1,1-二氟乙氧基)苯基]-氨基]-羰基]-苯甲酰基,
氨基甲酸3-甲基苯基丙酯,
4-[4-(4-乙氧基苯基)-4-甲基戊基]-1-氟-2-苯氧基-苯,
4-氯-2-(1,1-二甲基乙基)-5-[[2-(2,6-二甲基-4-苯氧基苯氧基)乙基]硫基]-3(2H)-哒嗪酮,
4-氯-2-(2-氯-2-甲基丙基)-5-[(6-碘-3-吡啶基)甲氧基]-3(2H)-哒嗪酮,
4-氯-5-[(6-氯-3-吡啶基)甲氧基]-2-(3,4-二氯苯基)-3(2H)-哒嗪酮,
苏云金芽孢杆菌菌株EG-2348,
[2-苯甲酰基-1-(1,1-二甲基乙基)-苯甲酰肼,
丁酸2,2-二甲基-3-(2,4-二氯苯基)-2-氧代-1-氧杂螺[4.5]十二烷-3-烯-4-酯,
二氢-2-(硝基亚甲基)-2H-1,3-噻嗪-3(4H)-甲醛,
[2-[[1,6-二氢-6-氧代-1-(苯基甲基)-4-哒嗪基]氧基]乙基]-氨基甲酸乙酯,
N-(3,4,4-三氟-1-氧代-3-丁烯基)-甘氨酸,
N-(4-氨苯基)-3-[4-(二氟甲氧基)苯基]-1-4,5-二氢-4-苯基-1H-吡唑-1-甲酰胺,
N-[(2-氯-5-噻唑基)甲基]-N’-甲基-N″-硝基-胍,
N-甲基-N’-(1-甲基-2-丙烯基)-1,2-肼二硫代二甲酰胺,
N-甲基-N’-2-丙烯基-1,2-肼二硫代二甲酰胺,
O,O-二乙基[2-(二丙基氨基)-2-氧代乙基]-乙基氨基硫代磷酸酯。
也可以是与其它已知的活性化合物例如除草剂,肥料和生长调节物质的混合物。
活性化合物可以使用其自身或者以其制剂形式使用或者以从中制备的使用形式使用,例如即用型溶液,混悬液,可湿粉剂,糊剂,可溶粉剂,细粉剂和颗粒剂。以常规方法使用,例如通过浇灌,喷雾,弥雾,散播,撒细粉,发泡,刷涂在其上等。此外还能通过超低体积方法施用活性化合物,或者将活性化合物制剂或活性化合物本身注入土壤。也可以处理植物的种子。
当使用本发明的活性化合物作为杀真菌剂时,施用比例可以在相当宽的范围内变化,取决于施用类型。处理植物部分时,活性化合物施用比例-般是0.1和10000g/ha之间,优选在10-1000g/ha之间。在处理种子时,活性化合物施用比例一般是每千克种子用0.001-50g,优选0.01-10g。处理土壤情况下,活性化合物施用比例一般是0.1和10000g/ha之间,优选在1和5000g/ha之间。
用于保护工业材料的组合物一般含有1-95%,优选10-75%的活性物质。
本发明活性化合物的使用浓度取决于要防治的微生物的性质和发生情况和要保护的材料的组成。最佳用量能用试验系列方法确定。一般情况下,使用浓度在0.001-5%重量范围内,优选0.05-1.0%重量,该重量比以要保护的材料为基础计。
如果需要,在根据本发明的材料保护中使用的活性物质的作用效力和范围以及组合物、乳油或者最普通的能从中制备的制剂的作用效力和范围可以通过加入扩大作用范围或者实现特定作用例如另外保护以抗昆虫的其它抗微生物的活性化合物,杀真菌剂,杀细菌剂,除草剂,杀昆虫剂,或其它活性物质来增加。这些混合物可以具有比本发明化合物作用更广的作用范围。
本发明活性化合物的制备和应用可以从下面的实施例中看到。
制备实施例
将300g的2-[2-(1-氯环丙基)-3-(2-氯苯基)-2-羟基丙基]-2,4-二氢-[1,2,4]-三唑-3-硫酮的外消旋体在基于光学活性单体N-甲基丙烯酰基-L-亮氨酸-3-(2,4-二甲基戊基)酰胺的手性固定的硅胶相(CSP)上用乙酸乙酯作为移动相在室温(大约23℃)下用HPLC方法进行分批分离,每批0.2g。用光度计检测洗脱液。具体地,制备分离在下列条件下进行:
柱:如上所述的CSP,10μm;570*50mm ID
移动相:乙酸乙酯
流速:100ml/min
检测:UV;254nm
进样:0.2g,溶解在20ml乙酸乙酯中。
合并含有同一种对映体的洗脱部分并减压浓缩。然后将所得产物用甲苯重结晶。
在所述条件下,左旋对映体先洗脱下来,接着是右旋对映体。
由此得到了117g的2-[2-(1-氯环丙基)-3-(2-氯苯基)-2-羟基丙基]-2,4-二氢-[1,2,4]-三唑-3-硫酮的(-)对映体,为固体,熔点123-124℃。
比旋光[α]D 20=-55.5°(10mg/1ml氯仿)。
类似地,得到了119g的相应的(+)对映体,为固体,熔点122-123℃。
比旋光[α]D 20=-54.9°(10mg/1ml氯仿)。
应用实施例
实施例A
禾旋孢霉(Cochliobolus sativus)试验(大麦)/保护性的
溶剂: 10份重量的N-甲基-吡咯烷酮
乳化剂: 0.6份重量的烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将乳油稀释到期望的浓度。
为了试验保护性活性,以所述施用率用活性化合物制剂对幼嫩植物喷雾。喷雾层风干后,将禾旋孢霉的分生孢子悬浮液喷雾在植物上。将植物保持在温度20℃且相对空气湿度是100%的培养室中48小时。
将植物放置在温度20℃且相对空气湿度大约80%的温室中。
接种后7天进行评价。0%表示相当于对照物的效力,而100%的效力表示没有发现感染。
下面的表中给出了活性化合物、施用率和试验结果。
表A
禾旋孢霉试验(大麦)/保护性的
实施例B:
柄球菌属(Podosphaera)试验(苹果)/保护性的
溶剂:47份重量的丙酮
乳化剂:3份重量的烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将乳油稀释到期望的浓度。
为了试验保护活性,以所述施用率的活性化合物制剂喷雾幼小植物。喷雾层风干后,用苹果霉病原体苹果白粉病柄球菌(Podosphaeraleucotricha)的孢子水悬浮液接种植物。然后植物放置在温度大约23℃且相对空气湿度是大约70%的温室中。
接种后10天进行评价。0%表示相当于对照物的效力,而100%的效力表示没有发现感染。
下面的表中给出了活性化合物、施用率和试验结果。
表B
柄球菌属(Podosphaera)试验(苹果)/保护性的
实施例C:
钩丝壳属(Uncinula)试验(葡萄藤)/保护性的
溶剂:47份重量的丙酮
乳化剂:3份重量的烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将乳油稀释到期望的浓度。
为了试验保护活性,以所述施用率的活性化合物制剂喷雾幼小植物。喷雾层风干后,用钩丝壳菌线虫(Uncinula necator)的孢子水悬浮液接种植物。然后将植物放置在温度大约23℃且相对空气湿度是大约70%的温室中。
接种后14天进行评价。0%表示相当于对照物的效力,而100%的效力表示没有发现感染。
下面的表中给出了活性化合物、施用率和试验结果。
表C
钩丝壳菌属(Uncinula)试验(葡萄藤)/保护性的
实施例D:
黑星菌属(Venturia)试验(苹果)/治愈性的
溶剂:47份重量的丙酮
乳化剂:3份重量的烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将乳油稀释到期望的浓度。
为了试验治愈活性,用苹果病原菌苹果黑星菌(Venturiainaequalis)的分生孢子水悬浮液接种植物。将植物保留在大约20℃和100%相对空气湿度的培育室中1天,然后置于温室中。经过一定的小时数后,以所述施用率的活性化合物制剂喷雾植物。
然后,将植物放置在温度大约21℃且相对空气湿度是大约90%的温室中。
接种后12天进行评价。0%表示相当于对照物的效力,而100%的效力表示没有发现感染。
下面的表中给出了活性化合物、施用率和试验结果。
表D
黑星菌属(Venturia)试验(苹果)/治愈性的
实施例E:
Pyricularia试验(稻)/保护性的
溶剂:2.5份重量的丙酮
乳化剂:0.06份重量的烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂混合,用水和所述量的乳化剂将乳油稀释到期望的浓度。
为了试验保护活性,以所述的施用率,用活性化合物制剂喷雾幼小植物。喷雾层风干后,用Pyricularia oryzae的孢子水悬浮液对植物接种。然后将植物放置在温度25℃且相对空气湿度为100%的温室中。
接种后4天进行评价。0%表示相当于对照物的效力,而100%的效力表示没有发现感染。
下面的表中给出了活性化合物、施用率和试验结果。
表E
Pyricularia试验(稻)/保护性的
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EP0470600B1 (de) * | 1990-08-10 | 1997-05-07 | Novartis AG | Naphthylalkylaminopyrimidin-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Schädlingsbekämpfungsmittel |
JPH04202190A (ja) * | 1990-11-30 | 1992-07-22 | Kureha Chem Ind Co Ltd | 光学活性トリアゾール誘導体及び殺菌剤 |
FR2706456B1 (fr) * | 1993-06-18 | 1996-06-28 | Rhone Poulenc Agrochimie | Dérivés optiquement actifs de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides. |
JPH07149769A (ja) * | 1993-10-07 | 1995-06-13 | Sankyo Co Ltd | 光学活性な含ケイ素アゾール化合物 |
DE19528046A1 (de) * | 1994-11-21 | 1996-05-23 | Bayer Ag | Triazolyl-Derivate |
DE19535243A1 (de) * | 1995-09-22 | 1997-03-27 | Bayer Ag | Neue Zwischenprodukte für die Synthese von Bisphosphinverbindungen |
DE19546136A1 (de) * | 1995-12-11 | 1997-06-12 | Bayer Ag | Chirale stationäre Phasen für die chromatographische Trennung von optischen Isomeren |
DE19652239A1 (de) * | 1996-12-16 | 1998-06-18 | Bayer Ag | Verwendung von 7-(2-Oxa-5,8-diazabicyclo[4.3.0]non-8-yl)-chinolon- und -naphthyridoncarbonsäure-Derivaten zur Therapie von Helicobacter-pylori-Infektionen und den damit assoziierten gastroduodenalen Erkrankungen |
DE19744400A1 (de) * | 1997-10-08 | 1999-04-15 | Bayer Ag | Verfahren zur Herstellung von Triazolinthion-Derivaten |
DE19839688A1 (de) * | 1997-10-08 | 1999-04-15 | Bayer Ag | Verfahren zur Herstellung von Triazolinthion-Derivaten |
DE19744401A1 (de) * | 1997-10-08 | 1999-04-15 | Bayer Ag | Verfahren zur Herstellung von Triazolinthion-Derivaten |
DE19744706A1 (de) * | 1997-10-10 | 1999-04-15 | Bayer Ag | Verfahren zur Herstellung von Triazolinthion-Derivaten |
-
1999
- 1999-04-19 DE DE19917617A patent/DE19917617A1/de not_active Withdrawn
-
2000
- 2000-04-06 BR BR0009844-2A patent/BR0009844A/pt not_active Application Discontinuation
- 2000-04-06 PL PL351544A patent/PL198924B1/pl unknown
- 2000-04-06 IL IL14543600A patent/IL145436A0/xx active IP Right Grant
- 2000-04-06 WO PCT/EP2000/003066 patent/WO2000063188A1/de active IP Right Grant
- 2000-04-06 AT AT00926822T patent/ATE299869T1/de active
- 2000-04-06 AU AU45441/00A patent/AU768630B2/en not_active Expired
- 2000-04-06 KR KR1020017012017A patent/KR100591606B1/ko active IP Right Grant
- 2000-04-06 ES ES00926822T patent/ES2243262T3/es not_active Expired - Lifetime
- 2000-04-06 CA CA002367361A patent/CA2367361C/en not_active Expired - Lifetime
- 2000-04-06 HU HU0201665A patent/HU228755B1/hu unknown
- 2000-04-06 RU RU2001131107A patent/RU2238270C2/ru active
- 2000-04-06 NZ NZ514859A patent/NZ514859A/xx not_active IP Right Cessation
- 2000-04-06 DE DE50010756T patent/DE50010756D1/de not_active Expired - Lifetime
- 2000-04-06 MX MXPA01010548A patent/MXPA01010548A/es active IP Right Grant
- 2000-04-06 PT PT00926822T patent/PT1173425E/pt unknown
- 2000-04-06 DK DK00926822T patent/DK1173425T3/da active
- 2000-04-06 CN CNB00806489XA patent/CN1214015C/zh not_active Expired - Lifetime
- 2000-04-06 JP JP2000612280A patent/JP4790128B2/ja not_active Expired - Lifetime
- 2000-04-06 EP EP00926822A patent/EP1173425B1/de not_active Expired - Lifetime
- 2000-04-13 AR ARP000101717A patent/AR023483A1/es active IP Right Grant
- 2000-04-18 TW TW089107647A patent/TWI254709B/zh not_active IP Right Cessation
-
2001
- 2001-09-12 ZA ZA200107519A patent/ZA200107519B/xx unknown
- 2001-09-13 IL IL145436A patent/IL145436A/en not_active IP Right Cessation
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2007
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Also Published As
Publication number | Publication date |
---|---|
PL198924B1 (pl) | 2008-07-31 |
AR023483A1 (es) | 2002-09-04 |
PT1173425E (pt) | 2005-10-31 |
TWI254709B (en) | 2006-05-11 |
US20080113864A1 (en) | 2008-05-15 |
WO2000063188A1 (de) | 2000-10-26 |
MXPA01010548A (es) | 2002-06-04 |
EP1173425A1 (de) | 2002-01-23 |
CA2367361A1 (en) | 2000-10-26 |
EP1173425B1 (de) | 2005-07-20 |
HU228755B1 (en) | 2013-05-28 |
NZ514859A (en) | 2003-01-31 |
CN1347409A (zh) | 2002-05-01 |
DE19917617A1 (de) | 2000-10-26 |
AU768630B2 (en) | 2003-12-18 |
HUP0201665A3 (en) | 2005-10-28 |
IL145436A (en) | 2006-08-20 |
CA2367361C (en) | 2007-07-31 |
DE50010756D1 (de) | 2005-08-25 |
AU4544100A (en) | 2000-11-02 |
PL351544A1 (en) | 2003-05-05 |
JP4790128B2 (ja) | 2011-10-12 |
ATE299869T1 (de) | 2005-08-15 |
ES2243262T3 (es) | 2005-12-01 |
IL145436A0 (en) | 2002-06-30 |
KR100591606B1 (ko) | 2006-06-20 |
KR20020002485A (ko) | 2002-01-09 |
RU2238270C2 (ru) | 2004-10-20 |
ZA200107519B (en) | 2002-11-27 |
DK1173425T3 (da) | 2005-11-14 |
JP2002542236A (ja) | 2002-12-10 |
BR0009844A (pt) | 2002-01-08 |
US8188129B2 (en) | 2012-05-29 |
HUP0201665A2 (en) | 2002-09-28 |
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