CN1242769A - 芳硫基二噻嗪二氧化物及其作为农药的应用 - Google Patents
芳硫基二噻嗪二氧化物及其作为农药的应用 Download PDFInfo
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- CN1242769A CN1242769A CN 97181236 CN97181236A CN1242769A CN 1242769 A CN1242769 A CN 1242769A CN 97181236 CN97181236 CN 97181236 CN 97181236 A CN97181236 A CN 97181236A CN 1242769 A CN1242769 A CN 1242769A
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- carbon atom
- alkyl
- atom
- dioxy
- methylene
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Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明公开了具有通式(Ⅰ)的化合物,其中R1,R2,R3和R4各自独立地代表氢,任选被取代的烷基、链烯基、炔烃基或芳基;和Ar代表任选被取代的芳基。这些化合物具有强的杀微生物作用,可以用来防治不期望的微生物,优选真菌和细菌,因此用来保护植物和材料。
Description
本发明涉及新的S-芳基-二噻嗪二氧化物,它们的制备方法和它们在农作物保护和材料保护中的应用。
已经描述过在S上具有烷基取代基的二噻嗪二氧化物,没有提到过生物活性(参见Nakahashi,K.等,Bull.Chem.Soc.Jpn.45,3217(1972);Masegawa,K等,Bull.Chem.Soc.Jpn.45,1567(1972))。
式(I)提供了本发明化合物的一般定义。优选给出下列式(I)化合物,其中R1,R2,R3和R4各自独立地代表氢,具有1-10个碳原子的直链和支链的烷基,具有2-10个碳原子的直链或支链的链烯基或者具有2-10个碳原子的直链或支链的炔烃基,这些基团任选被相同或不同的选自下组的取代基一至多取代:卤素,具有1-6个碳原子的烷氧基,具有1-6个碳原子和1-9个相同或不同的卤原子的卤代烷氧基,具有1-6个碳原子的烷硫基,具有1-6个碳原子和1-9个相同或不同的卤原子的卤代烷硫基,具有1-6个碳原子的酰基,具有1-6个碳原子的酰氧基,具有1-6个碳原子的(烷氧)羰基,氨基,其任选被相同或不同的选自烷基和芳基的取代基取代,任选被取代的苯氧基、芳基、吡啶基或吡啶基氧基,硝基或氰基,或者代表芳基,其任选被卤素,具有1-10个碳原子的烷基,具有1-8个碳原子和1-8个相同或不同的卤原子的卤代烷基,具有1-10个碳原子的烷氧基,具有1-8个碳原子和1-8个相同或不同的卤原子的卤代烷氧基,具有1-10个碳原子的烷硫基,具有1-8个碳原子和1-8个相同或不同的卤原子的卤代烷硫基,氨基,带有直链或支链的具有1-6个碳原子的烷基的一烷基氨基,带有相同或不同的各具有1-6个碳原子的直链或支链的烷基的二烷基氨基,具有1-6个碳原子的环烷基,亚甲二氧基,二氟亚甲二氧基,氯代氟代亚甲二氧基,二氨亚甲二氧基,硝基或氰基一至五取代,和Ar 代表芳基,其任选被卤素,具有1-10个碳原子的烷基,具有1-8个碳原子和1-8个相同或不同的卤原子的卤代烷基,具有1-10个碳原子的烷氧基,具有1-8个碳原子和1-8个相同或不同的卤原子的卤代烷氧基,具有1-10个碳原子的烷硫基,具有1-8个碳原子和1-8个相同或不同的卤原子的卤代烷硫基,氨基,带有直链或支链的具有1-6个碳原子的烷基的一烷基氨基,带有相同或不同的各具有1-6个碳原子的直链或支链的烷基的二烷基氨基,具有1-6个碳原子的环烷基,亚甲二氧基,二氟亚甲二氧基,氯代氟代亚甲二氧基,二氯亚甲二氧基,硝基或氰基一至五取代。
特别优选给出下列式(I)化合物,其中R1,R2,R3和R4各自独立地代表氢,具有1-8个碳原子的直链和支链的烷基,具有2-8个碳原子的直链或支链的链烯基或者具有2-8个碳原子的直链或支链的炔烃基,这些基团任选被相同或不同的选自下组的取代基一至四取代:氟,氯,具有1-5个碳原子的烷氧基,具有1-5个碳原子和1-5个氟和/或氯原子的卤代烷氧基,具有1-5个碳原子的烷硫基,具有1-5个碳原子和1-5个氟和/或氯原子的卤代烷硫基,具有1-5个碳原子的酰基,具有1-5个碳原子的酰氧基,具有1-5个碳原子的烷氧羰基,氨基,其任选被相同或不同的选自具有1-4个碳原子的烷基和苯基的取代基取代,任选被取代的苯氧基、芳基、吡啶基、吡啶基氧基,硝基或氰基,或者代表苯基,其任选被氟,氯,具有1-8个碳原子的烷基,具有1-6个碳原子和1-6个氟和/或氯原子的卤代烷基,具有1-8个碳原子的烷氧基,具有1-6个碳原子和1-6个氟和/或氯原子的卤代烷氧基,具有1-8个碳原子的烷硫基,具有1-6个碳原子和1-6个氟和/或氯原子的卤代烷硫基,氨基,带有具有1-4个碳原子的烷基的一烷基氨基,带有相同或不同的各具有1-4个碳原子的烷基的二烷基氨基,具有1-6个碳原子的环烷基,亚甲二氧基,二氟亚甲二氧基,氯代氟代亚甲二氧基,二氯亚甲二氧基,硝基或氰基一至四取代,和Ar 代表苯基,其任选被氟,氯,溴,具有1-8个碳原子的烷基如优选甲基,乙基,正丙基,异丙基,正-、异-、仲-或叔-丁基,具有1-6个碳原子和1-6个氟和/或氯原子的卤代烷基如优选三氟甲基,三氟乙基,二氟氯代甲基,具有1-8个碳原子的烷氧基如优选甲氧基,乙氧基,正-或异-丙氧基,正-、异-、仲-或叔-丁氧基,具有1-6个碳原子和1-6个氟和/或氯原子的卤代烷氧基如优选二氟甲氧基,三氟甲氧基,二氟氯代甲氧基,三氟乙氧基,具有1-8个碳原子的烷硫基,具有1-6个碳原子和1-6个氟和/或氯原子的卤代烷硫基,氨基,带有具有1-4个碳原子的烷基的一烷基氨基,带有相同或不同的各具有1-4个碳原子的烷基的二烷基氨基,具有1-6个碳原子的环烷基,亚甲二氧基,二氟亚甲二氧基,氯代氟代亚甲二氧基,二氯亚甲二氧基,硝基或氰基一至四取代,优选一至二取代。
R1,R2,R3和R4各自特别优选代表氢和/或甲基。
在基团各组合或优选的组合中对各基团给出的具体基团定义,独立于给定的具体组合,也可以根据需要由其它优选范围的基团定义代替。
此外,发现如果在含水/碱性溶液中,如果适当在催化剂存在下,通式(II)的盐与通式(III)的重氮盐反应,则得到式(I)的化合物其中R1,R2,R3和R4各自如上定义,和M代表碱金属离子或碱土金属离子,特别是Na+,K+,
Ar-N≡NAθ (III)其中Ar如上定义,和Aθ代表无机酸的阴离子。
优选地,向(II)的溶液中加入碱和,如果适当,催化剂,然后加入重氮盐溶液(III)。使用的优选的碱是碱金属氢氧化物,例如氢氧化钾或氢氧化钠。
合适的催化剂是促进重氮官能团变化为含硫基团的所有的催化剂。
优选使用Cu(I)盐或铜粉。加入重氮盐溶液期间的温度可以在很宽的范围内变化。一般情况下,反应在-30℃和+60℃之间,优选-20℃和+40℃之间进行。从苯胺制备重氮盐溶液的反应通过文献方法进行。
通式(II)的盐中的一些是已知的,或者其可以通过类似于文献那些已知的方法制备(参见文献参考p.1)。也可以使用以固体形式分离出来的式(II)的盐或者就地制备的溶液。
本发明活性化合物具有强的杀微生物作用并且可以用来在农作物保护和材料保护中防治不期望的微生物,优选真菌和细菌。
本说明书中术语工业材料是指制备出来用于工业的无生命材料。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能的例子是粘合剂,胶料,纸张和纸板,纺织品,皮革,木材,涂料组合物和塑料制品,冷却润滑剂和其它能被微生物侵蚀或破坏的材料。可提及的要保护的材料还可以是生产工厂的部分,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。
可以导致工业材料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。本发明活性化合物或组合物优选作用于细菌,真菌,特别是霉菌,还杀粘液生物和藻。
通过举例,可以提到下面属种微生物: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(Escherichiacoli),假单孢菌属(Pseudomonas),例如铜绿假单孢菌(Pseudomonasaeruginosa),葡萄球菌属(Staphylococcus),例如金黄色葡萄球菌(Staphylococcus aureus)。
农作物保护中使用杀真菌剂来防治根肿菌(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)。
作为例子可以提到上述属名下的真菌疾病的一些病原体,但是不受此限制: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);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(Sphaerothecafuliginea);柄球菌属种类(Podosphaera),例如苹果白粉病柄球菌(Podosphaeraleucotricha);黑星菌属种类(Venturia),例如苹果黑星菌(Venturia inaequalis);核腔菌属种类(Pyrenophora),例如圆核腔菌(Pyrenophora teres)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(Cochliobolus),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(Uromycesappendiculatus);柄锈菌属种类(Puccinia),例如隐匿柄锈菌(Puccinia recondita);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(Botrytis cinerea);壳针孢属种类(Septoria),例如颖枯壳针孢(Septoria nodorum);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(Alternariabrassicae);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的事实允许处理值物。可以处理植物的地上部分,也可以处理植物繁殖根株和种子,和处理土壤。
根据其各自的物理和/或化学性质,式(I)的活性化合物可以配制成常规制剂,例如溶液、乳剂、悬浮剂、粉剂、泡沫剂、糊剂、颗粒剂、气雾剂,包裹在聚合物中的细微胶囊。
这些制剂和组合物可以用已知的方式制备,例如,通过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,甲苯和烷基萘,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,如二甲基甲酰胺或二甲亚砜,以及水;液化气体扩充剂或载体理解为指常温常压下是气体的液体,例如气雾抛射剂,例如卤代烃,还有丁烷,丙烷,氮和二氧化碳。适合的固体载体是: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;用于颗粒剂的适合的固体载体是: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;适合的乳化剂和/或起泡剂有: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;适合的分散剂是: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。其它可能的添加剂是矿物油和植物油。
也可以使用着色剂,如无机颜料,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。
式(I)的活性化合物以及可由之制备的组合物、前体或制剂的效力和活性谱(如果需要)一般可以通过添加其它抗微生物化合物、杀真菌剂、杀细菌剂、除草剂、杀虫剂或其它活性化合物而增加,由此拓宽活性谱或获得特别的效果,例如附加的抵御昆虫的保护。这些混合物可以具有比本发明化合物宽的活性谱。
在许多情况下,获得增效效果,即混合物的活性大于各组分的活性。特别适合的共组分是例如下列化合物:三唑类,如三唑锡、双苯三唑醇、糠菌唑、苄氯三唑醇、噁醚唑、烯唑醇、环氧唑(epoxyconazole)、乙环唑、fenbuconazole、解草唑、fenethanil、fluquinconazole、氟硅唑、粉唑醇、呋菌唑、己唑醇、酰胺唑、ipconazole、isozofos、腈菌唑、metconazole、多效唑、戊菌唑、丙环唑、(±)-顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇、2-(1-叔丁基)-1-(2-氯代苯基)-3-(1,2,4-三唑-1-基)-丙-2-醇、氟醚唑、三唑酮、三唑醇、抑芽唑、氟菌唑、triticonazole、烯效唑及它们的金属盐和酸加成物。咪唑类,如clotrimazole、bifonazole、咪菌酮、econazole、咪菌腈、抑霉唑、isoconazole、ketoconazole、lombazole、稻瘟酯、咪鲜安、氟菌唑、thiazolcar、1-咪唑基-1-(4’-氯苯氧基)-3,3-二甲基丁-2-酮,及它们的金属盐和酸加成物。吡啶类和嘧啶类,如三环苯嘧醇,丁噻特,氯苯嘧啶醇,氟苯嘧啶醇,triamirol;琥珀酸脱氢酶抑制剂,如邻碘酰苯胺、莠锈灵、增效砜、环菌胺、甲呋酰苯胺、flutanil、二甲呋酰苯胺、拌种胺、邻酰胺、灭锈胺、呋菌胺、噻菌胺、pyrocarbolid、氧化防霉胺、氟酰胺、拌种灵(seedvax);萘衍生物,如特比萘芬、萘替芬、布替萘芬、3-氯-7-(2-氮杂-2,7,7-三甲基-辛-3-烯-5-炔);亚磺酰胺类,如苯氟磺胺、甲苯氟磺胺、灭菌丹、氟灭菌丹(fluorfolpet);克菌丹、敌菌丹;苯并咪唑类,如多菌灵、苯菌灵、麦穗宁、噻菌灵及它们的盐;吗啉衍生物,如aldimorph、烯酰吗啉、十二环吗啉、falimorph、苯锈啶,丁苯吗啉、十三吗啉、trimorphamid及它们的芳磺酸类,例如对甲苯磺酸和对十二烷基苯基磺酸;苯并噻唑类,如2-巯基苯并噻唑;苯并噻吩二氧化物,如N-环己基-苯并[b]噻吩甲酰胺S,S-二氧化物;苯甲酰胺类,如2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺,叶枯肽;硼化合物,如硼酸、硼酸酯、硼砂;甲醛及释放甲醛的化合物如苄基醇单(多)半缩甲醛、正丁醇半缩甲醛、棉隆,乙二醇半缩甲醛、六氢-S-三嗪类、六亚甲基四胺,N-羟基甲基-N’-甲基硫脲、N-甲基醇氯乙酰胺、噁唑烷、多聚甲醛、taurolin、四氢-1,3-噁嗪、N-(2-羟基丙基)-胺-甲醇;异噻唑啉酮类,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、5-氯-N-辛基异噻唑啉酮、N-辛基异噻唑啉-3-酮、4,5-三亚甲基-异噻唑啉酮、4,5-苯并异噻唑啉酮;醛类,如月桂醛、甲醛、戊二醛、β-溴月桂醛;硫氰酸酯类,如氰硫基甲基硫基苯并噻唑、甲撑双硫氰酸酯;季铵盐化合物,如benzalkonium chloride、苄基二甲基十四烷基氯化铵、苄基二甲基十二烷基氯化铵、二氯苄基二甲基烷基氯化铵、二癸基二甲基氯化铵、二辛基二甲基氯化铵、N-十六-烷基-三甲基氯化铵,1-十六烷基-吡啶鎓氯化物;碘衍生物,如二碘甲基对甲苯基砜、3-碘-2-丙炔醇、4-氯苯基-3-碘炔丙基缩甲醛、3-溴-2,3-二碘-2-丙烯基 乙基氨基甲酸酯、2,3,3-三碘烯丙基醇、3-溴-2,3-二碘-2-丙烯基醇、3-碘-2-丙炔基正丁基氨基甲酸酯、3-碘-2-丙炔基 正己基氨基甲酸酯、3-碘-2-丙炔基 环己基氨基甲酸酯、3-碘-2-丙炔基苯基氨基甲酸酯;苯酚衍生物,如三溴苯酚、四氯苯酚、3-甲基-4-氯苯酚、3,5-二甲基-4-氯苯酚、苯氧基乙醇、二氯苯酚、2-苄基-4-氯苯酚、5-氯-2-(2,4-二氯苯氧基)-苯酚、六氯酚、对羟基苯甲酸酯、邻苯基苯酚、间苯基苯酚、对苯基苯酚及它们的碱金属和碱土金属盐;具有活化的卤素基团的杀微生物剂,如bronopol、bronidox、2-溴-2-硝基-1,3-丙二醇、2-溴-4’-羟基-苯乙酮、1-溴-3-氯-4,4,5,5-四甲基-2-咪唑烷酮、β-溴-β-硝基苯乙烯、氯代乙酰胺、chloramineT、1,3-二溴-4,4,5,5-四甲基-2-咪唑烷酮、dichloramine T、3,4-二氯-(3H)-1,2-二硫醇-3-酮、2,2-二溴-3-腈-丙酰胺、1,2-二溴-2,4-二氰基丁烷、卤胺、卤胺腙、粘氯酸、苯基(2-氯-氰基-乙烯基)砜、苯基(1,2-二氯-2-氰基-乙烯基)砜、三氯异氰脲酸;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、吡啶甲醇、嘧菌胺、吡菌硫、1-羟基-4-甲基-6-(2,4,4-三甲基戊基)-2(1H)-吡啶;甲氧基丙烯酸酯或类似物,如(E)-甲氧基亚氨基[α-(邻-甲苯氧基)-邻-甲苯基]乙酸甲酯,(E)-2-甲氧基亚氨基-N-甲基-2-(2-苯氧基苯基)乙酰胺,(E)-2-[2-[6-(2-氰基苯氧基)嘧啶-4-基氧基]苯基]-3-甲氧基丙烯酸酯O-甲基-2-[([3-甲氧基亚氨基-2-丁基]亚氨基)氧基]邻-甲苯基]-2-甲氧基亚氨基乙亚胺酸酯,2-[[[[1-(2,5-二甲基苯基)亚乙基]氨基]氧基]甲基]-α-(甲氧基亚氨基)-N-甲基-苯乙酰胺,α-(甲氧基亚氨基)-N-甲基-2-[[[[1-[3-(三氟甲基)苯基]亚乙基]氨基]氧基]甲基]-苯乙酰胺,α-(甲氧基亚氨基)-2-[[[[1-[3-(三氟甲基)苯基]亚乙基]氨基]氧基]甲基]-苯乙酸甲酯,α-(甲氧基亚甲基)-2-[[[[1-[3-(三氟甲基)苯基]亚乙基]氨基]氧基]甲基]-苯乙酸甲酯,2-[[[5-氯-3-(三氟甲基)-2-吡啶基]氧基]甲基]-α-(甲氧基亚甲基)-N-甲基-苯乙酰胺,2-[[[环丙基[(4-乙氧基苯基)亚氨基]甲基]硫基]甲基]-α-(甲氧基亚氨基)-苯乙酸甲酯,α-(甲氧基亚氨基)-N-甲基-2-(4-甲基-5-苯基-2,7-二氧杂-3,6-二氮杂辛-3,5-二烯-1-基)-苯乙酰胺,α-(甲氧基亚甲基)-2-(4-甲基-5-苯基-2,7-二氧杂-3,6-二氮杂辛-3,5-二烯-1-基)-苯乙酸甲酯,α-(甲氧基亚氨基)-N-甲基-2-[[[[1-3-(三氟甲基)苯基]乙氧基]亚氨基]甲基]-苯乙酰胺,2-[[(3,5-二氯-2-吡啶基)氧基]甲基]-α-(甲氧基亚氨基)-N-甲基-苯乙酰胺,2-[4,5-二甲基-9-(4-吗啉基)-2,7-二氧杂-3,6-二氮杂壬-3,5-二烯-1-基]-α-(甲氧基亚甲基)-苯乙酸甲酯;金属皂,如环烷酸锡、环烷酸铜、环烷酸锌、辛酸锡、辛酸铜、辛酸锌、2-乙基己酸锡、2-乙基己酸铜、2-乙基己酸锌、油酸锡、油酸铜、油酸锌、磷酸锡、磷酸铜、磷酸锌、苯甲酸锡、苯甲酸铜和苯甲酸锌;金属盐,如碱式碳酸铜、重铬酸钠、重铬酸钾、铬酸钾、硫酸铜、氯化铜、硼酸铜、氟硅酸锌、氟硅酸铜;氧化物,如三丁基锡氧化物、氧化亚铜、氧化铜、氧化锌;二硫代氨基甲酸酯类,如代森盐,福美铁,N-羟基甲基-N’-甲基二硫基氨基甲酸钾,二甲基二硫基氨基甲酸的钠盐或钾盐,macozeb,代森锰,威百亩,代森联,福美双,代森锌,福美锌;腈类,如2,4,5,6-四氯间苯二腈、氰基二硫代亚氨基氨基甲酸酯二钠盐;喹啉类,如8-羟基喹啉及它们的铜盐;其它杀真菌剂和杀细菌剂,例如5-羟基-2(5H)-呋喃酮;4,5-苯并二噻唑啉酮、4,5-三亚甲基二噻唑啉酮、N-(2-对氯苯甲酰乙基)-六铵氯化物、2-氧代-2-(4-羟基-苯基)-乙羟肟酰氯,三-N-(环己基二氮烯鎓二氧基)-铝,N-(环己基二氮烯鎓二氧基)-三丁基锡或钾盐,双-N-(环己基二氮烯鎓二氧基)-铜,含银、锌或铜的沸石,它们可以是单独的或包封在聚合物材料中。
非常特别优选的混合物是与下列活性成分的混合物:戊环唑、糠菌唑、环唑醇、苄氯三唑醇、烯唑醇、己唑醇、metaconazole、戊菌唑、丙环唑、戊唑醇、苯氟磺胺,甲苯氟磺胺,fluorfolpet、呋菌胺、萎锈灵、N-环己基-苯并[b]噻吩甲酰胺S,S-二氧化物,拌种咯、4-(2,2-二氟-1,3-苯并二氧戊环-4-基)-1H-吡咯-3-腈、布替萘芬、抑霉唑、N-甲基-异噻唑啉-3-酮、5-氯-N-甲基异噻唑啉-3-酮、N-辛基异噻唑啉-3-酮、二氯-N-辛基异噻唑啉酮,巯基苯并噻唑、氰硫基甲基硫基苯并噻唑,苯并异噻唑啉酮,N-(2-羟基丙基)-氨基-甲醇、苄醇(半)甲缩醛、N-甲基醇氯代乙酰胺,N-(2-羟基苯基)-胺-甲醇,戊二醛、万亩定、二碳酸二甲酯和/或3-碘-2-丙炔基正丁基氨基甲酸酯。
此外,除上述杀真菌剂和杀细菌剂外,有高度活性的混合物还可以用其它活性化合物制备: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,艾氏剂,烯丙菊酯,甲体氯氰菊酯,双虫脒,阿凡曼菌素,AZ60541,azadirachtin,azinphos-A,保棉磷,三唑锡,苏云金杆菌,熏虫菊酯,4-溴-2-(4-氯代苯基)-1-(乙氧基甲基)-5-(三氟甲基)-1H-吡咯-3-腈,噁虫威,丙硫克百威,杀虫磺,氟氯氰菊酯,氟氯菊酯,生物苄呋菊酯,生物烯丙菊酯,溴硫磷A,溴硫磷M,合杀威,噻嗪酮,butathiophos,butocarboxin,butoxycarboxim,硫线磷,甲萘威,克百威,三硫磷,丁硫克百威,杀螟丹,灭螨猛,除线威,氯丹,chlorethoxyfos,毒虫畏,定虫隆,氯甲硫磷,N-[(6-氯-3-吡啶基)甲基]-N’-氰基-N-甲基乙亚胺酰胺,chlorpicrin,毒死蜱A,毒死蜱M,顺式-苄呋菊酯,clocythrin,cypophenothrin,四螨嗪,蝇毒磷,杀螟腈,乙氰菊酯,氟氯氰菊酯,cyhalothrin,三环锡,氯氰菊酯,灭蝇胺,溴氰菊酯(decamethrin,deltamethrin),内吸磷-M,内吸磷-S,甲基内吸磷,杀螨隆,氯亚胺硫磷,二嗪磷,1,2-二苯甲酰基-1-(1,1-二甲基)-肼,DNOC,酚线磷,敌敌畏,dicliphos,百治磷,除虫脲,乐果,二甲基-(苯基)-甲硅烷基-甲基-3-苯氧基苄基醚,二甲基-(4-乙氧基苯基)-甲硅烷基甲基-3-苯氧基苄基醚,甲基毒虫畏,敌恶磷,乙拌磷,eflusilanate,emamectin,烯炔菊酯,硫丹,EPN,高氰戊菊酯,乙硫苯威,乙硫磷,醚菊酯,乙嘧硫磷,虫胺磷,喹螨醚,苯丁锡,五氟苯菊酯,杀螟硫磷,仲丁威,苯硫威,双氧威,甲氰菊酯,fenpyrad,唑螨酯,线虫磷,倍硫磷,氰戊菊酯,fipronil,fluazuron,氟螨脲,氟氰戊菊酯,氟虫脲,氟氯苯菊酯,flufenprox,氟胺氰菊酯,地虫硫磷,伐虫脒,安果,丁苯硫磷,噻唑磷,fubfenprox,呋线威,HCH,庚烯磷,氟铃脲,噻螨酮,伏义腙,烯虫乙酯,吡虫啉,碘硫磷,异稻瘟净,氯唑磷,isoamidophos,异丙胺磷,叶蝉散,稻瘟灵,噁唑磷,异阿凡曼菌素,lama-氯氟氰菊酯,kadedrin-氯氟氰菊酯,lufenuron,马拉硫磷,灭蚜蜱,速灭磷,mesulfenphos,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,moxidectin,二溴磷,NC184,NI25,烟碱,nitenpyram,氧乐果,杀线威,亚砜吸磷,异砜磷,对硫磷-A,对硫磷-M,氟幼脲,氯菊酯,2-(4-苯氧基苯氧基)-乙基乙基氨基甲酸酯,稻丰散,甲拌磷,伏杀硫磷,亚胺硫磷,磷胺,辛硫磷,抗芽威,甲基嘧啶磷,嘧啶磷-A,炔酮菊酯,丙溴磷,猛杀威,丙虫磷,残杀威,丙硫磷,发果,pymetrozin,吡唑硫磷,pyradaphenthion,pyresmethrin,除虫菊酯,哒螨酮,pyrimidifen,蚊蝇醚,喹硫磷,生物苄呋菊酯,RH7988,鱼藤酮,蔬果磷,sebufos,silafluofen,治螟硫磷,甲丙硫磷,氟胺氰菊酯,taroils,tebufenozid,tebufenpyrad,tebupirimiphos,伏虫隆,七氟菊酯,双硫磷,特灭威,特丁磷,杀虫畏,胺菊酯,tetramethacarb,thiafenox,蛾蝇腈,硫双威,久效磷,thiazophos,杀虫环,二甲硫吸磷,虫线磷,thuringiensin,四溴菊酯,苯噻螨,三唑磷,triazamate,triazuron,敌百虫,杀虫隆,混灭威,芽灭多,XMC,灭杀威,zetamethrin。杀软体动物剂:三苯基乙酸锡、蜗牛敌、灭梭威、贝螺杀;除草剂和杀藻剂:乙草胺、三氟羧草醚、苯草醚、丙烯醛、甲草胺、禾草灭、莠灭净、amidosulfuron、杀草强、氨基磺酸铵、莎稗磷、磺草灵、莠去津、aziptrotryne、azimsulfuron、草除灵、乙丁氟灵、呋草黄、苄嘧黄隆、地散磷、灭草松、吡草酮、苯噻隆、甲羧除草醚、硼砂、除草定、溴丁酰草胺、溴酚肟、溴苯腈、丁草胺、抑草磷、双丁乐灵、丁草特、双丙胺酰膦、新燕灵、卡草胺、甲氧除草醚、灭草平、绿秀隆、正形素、杀草敏、氯嘧黄隆、草枯醚、氯乙酸、绿麦隆、枯草隆、氯苯胺灵、绿黄隆、氯酞酸、草克乐、环庚草醚、醚黄隆、烯草酮、异噁草酮、chlomeprop、三氯吡啶酸、氰氨化钙、氰草津、灭草特、噻草酮、chloroxynil、clodinafop-propargyl、cumyluron、CGA248757、clometoxyfen、cyhalofop、clopyrasuluron、cyclosulfamuron、2,4-滴丙酸、高2,4-滴丙酸盐、禾草灵、乙酰甲草胺、枯莠隆、双苯唑快、吡氟草胺、丁噁隆、哌草丹、二甲草胺、噻节因、氨基乙氟灵、地乐酚、地乐酚乙酸盐、特乐酚、双苯酰草胺、异丙净、敌草快、氟硫草定、diduron、DNOC、DSMA、2,4-滴、杀草隆、茅草枯、棉隆、2,4-滴丁酸、甜菜安、敌草净、麦草畏、敌草腈、dimethamid、氟硫草定、二甲丙乙净、甘草津、茵多杀、EPTC、禾草畏、乙丁烯氟灵、赛黄隆、乙呋草黄、ethobenzanid、ethoxyfen、ET751、ethametsulfuron、噁唑禾草灵、高噁唑禾草灵、非草隆、麦草伏、麦草伏M、啶嘧黄隆、吡氟禾草灵、高吡氟禾草灵、fuenachlor、fluchloralin、伏草隆、乙羧氟草醚、氟化除草醚、四氟丙酸、芴丁酸、氟定酮、氟咯草酮、氟草烟、氟黄胺草醚、蔓草磷、麦草伏异丙酯、麦草伏异丙酯-L、flumiclorac-pentyl、flumipropyn、flumioxzim、flurtatone、flumioxzim、草甘磷、草铵磷、吡氟氯禾灵、环嗪酮、咪草酯、异丙隆、isoxaben、噁草醚、灭草烟、灭草喹、咪草烟、碘苯腈、异丙乐灵、imazosulfuron、KUH911、KUH920、乳氟禾草灵、环草定、利谷隆、磺草磷、2甲4氯、2甲4氯硫代乙酯、2甲4氯丁酸、2甲4氯丙酸、高2甲4氯丙酸、苯噻草胺、伏草胺、威百亩、苯嗪草酮、吡草胺、甲基苯噻隆、灭杀唑、甲氧丙净、methyldymron、异硫代氰酸甲酯、秀谷隆、甲氧隆、嗪草酮、甲黄隆、草达灭、庚草利、绿谷隆、甲基胂酸、丙草胺、metosulam、metobenzuron、萘丙草胺、萘氧丙草胺、萘草胺、草不隆、烟嘧黄隆、哒草灭,氯酚钠、噁草灵、乙氧氟甲草醚、orbencarb、黄草灭、quinchlorac、quinmerac、克稗尔、prosulfocarb、pyrazolate、pyrazolsulfuron、pyrazoxyfen、pyributicarb、pyridate、百草枯、克草猛、二甲戊乐灵、五氯酚、戊酰苯草胺、石油、甜菜宁、毒莠定、哌草磷、丙草胺、氟嘧黄隆、氨基丙氟灵、扑草净、毒草胺、敌稗,喔草酯、扑灭津、苯胺灵,pyrithiobac、喹草酸、灭藻醌、喹禾灵、高喹禾灵、rimsulfuron、稀禾定、sifuron、西玛津、西玛净、嘧黄隆、sulfentrazone、sulcotrione、草甘膦、重焦油、三氯乙酸、牧草胺、特丁噻草隆、特草定、特丁通、特丁津、特丁净、噻氟隆、噻黄隆、thiocarbazil、肟草酮、四溴菊酯、醚苯黄隆、苯黄隆、绿草定、灭草环、草达津、氟乐灵、乙嗪草酮、thdiazimin、thiazopyr、triflusulfuron、灭草猛。
活性化合物在这些活性化合物结合物中的重量比可以在较大的范围内变化。
活性化合物结合物优选含有0.1-99.9%,特别是1-75%,尤其优选5-50%量的活性化合物,其余部分为上述一种或多种共组分,补齐至100%。
用于保护工业材料的杀微生物组合物或浓缩物含有按重量计0.01至95%浓度,特别是按重量计0.1-60%的活性化合物或活性化合物结合物。
待用的本发明活性化合物或活性化合物结合物的使用浓度取决于要防治的微生物的种类和发生情况和要保护的材料的组成。最佳施用率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,该重量比是以要保护的材料为基础。
本发明活性化合物或组合物允许以有利的方式以更有效的组合物取代目前可以得到的杀微生物组合物。它们具有好的稳定性以及以有利的方式具有广的活性谱。
首先向26ml水和130ml丙酮中加入4.97g(0.024mol)1,1-二氧代-(1,4,2)二噻嗪烷-3-硫酮钠盐并且冷却到0℃。经8分钟向该混合物中滴加重氮盐溶液I。将该混合物首先在0℃下搅拌0.5小时,然后在室温下搅拌2小时。用二氯甲烷萃取混合物,有机相用1N盐酸和水洗涤,干燥,浓缩。残余物进行硅胶色谱。产量2.6g(=理论量的34%)。m.p.=166℃。重氮盐溶液I首先向46.8ml水和6.5ml盐酸(浓)中加入4.97g(0.024mol)4-氯代苯胺,冷却到0℃,并且滴加在15.6ml水中的1.9g NaNO2的溶液。将混合物搅拌1小时并且用6.3g乙酸钠调节至pH4.5。
表1(续)应用实施例A
为了证明防治真菌的效力,测定本发明试剂的最小抑制浓度(MIC):
将用麦芽提取液制备的琼脂以0.1mg/l至5000mg/l的浓度与本发明活性化合物混合。琼脂固化后,用表2列出的试验生物的纯的培养物污染琼脂。在28℃和60-70%相对空气湿度下贮存两星期后测定MIC。MIC是观察不到使用的微生物发生任何移生时的活性化合物的最低浓度。结果列在下表2中。表2 本发明式(I)化合物的最小抑制浓度(ppm)
实施例序号 | 1 | 2 | 5 |
短茎青霉 | <40 | <40 | <40 |
球毛壳霉 | <40 | <40 | <40 |
黑色曲霉 | <40 | 200 | <40 |
Claims (8)
2.权利要求1的式(I)的化合物,其中
R1,R2,R3和R4各自独立地代表氢,具有1-10个碳原子的直链和支链的烷基,具有2-10个碳原子的直链或支链的链烯基或者具有2-10个碳原子的直链或支链的炔烃基,这些基团任选被相同或不同的选自下组的取代基一至多取代:卤素,具有1-6个碳原子的烷氧基,具有1-6个碳原子和1-9个相同或不同的卤原子的卤代烷氧基,具有1-6个碳原子的烷硫基,具有1-6个碳原子和1-9个相同或不同的卤原子的卤代烷硫基,具有1-6个碳原子的酰基,具有1-6个碳原子的酰氧基,具有1-6个碳原子的(烷氧)羰基,氨基,其任选被相同或不同的选自烷基和芳基的取代基取代,任选被取代的苯氧基、芳基、吡啶基或吡啶基氧基,硝基或氰基,或者
代表芳基,其任选被卤素,具有1-10个碳原子的烷基,具有1-8个碳原子和1-8个相同或不同的卤原子的卤代烷基,具有1-10个碳原子的烷氧基,具有1-8个碳原子和1-8个相同或不同的卤原子的卤代烷氧基,具有1-10个碳原子的烷硫基,具有1-8个碳原子和1-8个相同或不同的卤原子的卤代烷硫基,氨基,带有直链或支链的具有1-6个碳原子的烷基的一烷基氨基,带有相同或不同的各具有1-6个碳原子的直链或支链的烷基的二烷基氨基,具有1-6个碳原子的环烷基,亚甲二氧基,二氟亚甲二氧基,氯代氟代亚甲二氧基,二氯亚甲二氧基,硝基或氰基一至五取代,
和
Ar 代表芳基,其任选被卤素,具有1-10个碳原子的烷基,具有1-8个碳原子和1-8个相同或不同的卤原子的卤代烷基,具有1-10个碳原子的烷氧基,具有1-8个碳原子和1-8个相同或不同的卤原子的卤代烷氧基,具有1-10个碳原子的烷硫基,具有1-8个碳原子和1-8个相同或不同的卤原子的卤代烷硫基,氨基,带有直链或支链的具有1-6个碳原子的烷基的一烷基氨基,带有相同或不同的各具有1-6个碳原子的直链或支链的烷基的二烷基氨基,具有1-6个碳原子的环烷基,亚甲二氧基,二氟亚甲二氧基,氯代氟代亚甲二氧基,二氯亚甲二氧基,硝基或氰基一至五取代。
3.权利要求1的式(I)的化合物,其中
R1,R2,R3和R4各自独立地代表氢,具有1-8个碳原子的直链和支链的烷基,具有2-8个碳原子的直链或支链的链烯基或者具有2-8个碳原子的直链或支链的炔烃基,这些基团任选被相同或不同的选自下组的取代基一至四取代:氟,氯,具有1-5个碳原子的烷氧基,具有1-5个碳原子和1-5个氟和/或氯原子的卤代烷氧基,具有1-5个碳原子的烷硫基,具有1-5个碳原子和1-5个氟和/或氯原子的卤代烷硫基,具有1-5个碳原子的酰基,具有1-5个碳原子的酰氧基,具有1-5个碳原子的烷氧羰基,氨基,其任选被相同或不同的选自具有1-4个碳原子的烷基和苯基的取代基取代,任选被取代的苯氧基、芳基、吡啶基、吡啶基氧基,硝基或氰基,或者代表苯基,其任选被氟,氯,具有1-8个碳原子的烷基,具有1-6个碳原子和1-6个氟和/或氯原子的卤代烷基,具有1-8个碳原子的烷氧基,具有1-6个碳原子和1-6个氟和/或氯原子的卤代烷氧基,具有1-8个碳原子的烷硫基,具有1-6个碳原子和1-6个氟和/或氯原子的卤代烷硫基,氨基,带有具有1-4个碳原子的烷基的一烷基氨基,带有相同或不同的各具有1-4个碳原子的烷基的二烷基氨基,具有1-6个碳原子的环烷基,亚甲二氧基,二氟亚甲二氧基,氯代氟代亚甲二氧基,二氯亚甲二氧基,硝基或氰基一至四取代,
和
Ar 代表苯基,其任选被氟,氯,溴,具有1-8个碳原子的烷基,具有1-6个碳原子和1-6个氟和/或氯原子的卤代烷基,具有1-8个碳原子的烷氧基,具有1-6个碳原子和1-6个氟和/或氯原子的卤代烷氧基,具有1-8个碳原子的烷硫基,具有1-6个碳原子和1-6个氟和/或氯原子的卤代烷硫基,氨基,带有具有1-4个碳原子的烷基的一烷基氨基,带有相同或不同的各具有1-4个碳原子的烷基的二烷基氨基,具有1-6个碳原子的环烷基,亚甲二氧基,二氟亚甲二氧基,氯代氟代亚甲二氧基,二氯亚甲二氧基,硝基或氰基一至四取代。
4.农药,其特征在于,含有至少一种权利要求1的式(I)的化合物。
5.防治害虫的方法,特征在于,使权利要求1的式(I)的化合物作用于害虫和/或其栖息地。
6.权利要求1-4的式(I)的化合物防治害虫的用途。
7.制备农药的方法,特征在于,将权利要求1-4的式(I)的化合物或组合物与扩充剂和/或表面活性剂混合。
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