CN1172479A - 酰基化的5-氨基吡咯 - Google Patents
酰基化的5-氨基吡咯 Download PDFInfo
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- CN1172479A CN1172479A CN95197297A CN95197297A CN1172479A CN 1172479 A CN1172479 A CN 1172479A CN 95197297 A CN95197297 A CN 95197297A CN 95197297 A CN95197297 A CN 95197297A CN 1172479 A CN1172479 A CN 1172479A
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Abstract
本发明涉及新的式(Ⅰ)酰基化的5-氨基吡唑及其制备方法和作为农药的应用,其中R1、R2、R3、R4和R5具有说明书中给出的含意。
Description
本发明涉及新的酰基化的5-氨基吡唑,其制备方法,以及其防治动物害虫,特别是防治出现在农业、森林、贮藏产品和材料保护以及卫生方面的昆虫、蜱螨和线虫的应用。
业已公开某些1-芳基-5-氨基吡唑衍生物(参见例如EP-A0 257 479和EP-A 0 243 636)具有杀虫和杀螨性能。
然而,这些化合物的作用效力和作用谱并不完全令人满意,特别是当其以低剂量和浓度使用时。
R1代表烷基、烷氧基烷基或卤代烷基,
R2代表氢、卤素、氰基、硝基、卤代烷硫基、烷氧羰基或链烯氧羰基,
R3代表烷基或任选取代的环烷基,
R4代表氢、烷基或任选取代的环烷基,且
R5代表基团-Y-R6,其中
Y代表任选取代的烷二基,和
R6代表在每种情况下任选取代的芳基或芳氧基。
此外,已发现可以如下获得式(I)的酰化5-氨基吡唑:
R1、R2、R3和R4具有上述含意,
在碱存在下和稀释剂存在下,与式(III)的酰基卤反应
R5-CO-Hal (III)其中
R5 具有上述含意,且
Hal代表卤素;
或
R1、R3、R4和R5具有上述含意,
(α)如果需要在稀释剂存在下和如果需要在催化剂存在下,与卤化剂反应,或
(β)如果需要在稀释剂存在下,与硝化剂反应。
最后,业已发现,式(I)的酰基化的5-氨基吡唑具有突出的生物性能,且最重要的是适合于防治动物害虫,特别是出现在农业、森林、贮藏产品和材料保护以及卫生方面的昆虫、蜱螨和线虫。
式(I)提供本发明的酰基化的5-氨基吡唑的一般定义。
上下文中所提到的结构式中给出的基团的优选取代基或范围在下文中作了说明。
R1优选代表C1-C4-烷基、C1-C4-烷氧基-C1-C4-烷基或C1-C4-卤代烷基,
R2优选代表氢、卤素、氰基、硝基、三氟甲硫基、二氟甲硫基、C1-C4-烷氧羰基或C2-C4-链烯氧羰基,
R3优选代表C1-C4-烷基,或代表C3-C6-环烷基,该环烷基任选被卤素或C1-C4-烷基取代,
R4优选代表氢、C1-C4-烷基,或代表C3-C6-环烷基,该环烷基任选被卤素或C1-C4-烷基取代,且
R5优选代表基团-Y-R6,其中
Y代表C1-C4-烷二基,该烷二基任选被卤素或C3-C6-环烷基取代,和
R6优选代表苯基或苯氧基,它们各任选被相同或不同的取代基单
至三取代,适合的取代基是卤素、硝基、氰基、C1-C12-烷基、
C1-C12-烷氧基、C1-C12-烷硫基、C1-C12-卤代烷基、C1-C12-卤
代烷氧基、C1-C12-卤代烷硫基、C2-C12-链烯基、C1-C12-烷氧基
-C2-C12-链烯基、C1-C4-烷硫基-C2-C12-链烯基、C2-C12-卤代链
烯基,和以及苯基、苯氧基、苯硫基或苄基,它们各任选被相同或
不同的下列基团单至三取代:卤素、硝基、氰基、C1-C4-烷基、
C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷
氧基或C1-C4-卤代烷硫基。
R1特别优选代表甲基、乙基、正或异丙基、或正、异、仲或叔丁基,或代表甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、三氟甲基、二氟甲基、氟甲基、1-氯-1-乙基或1-氟-1-乙基,
R2特别优选代表氢、氟、氯、溴、氰基、硝基、三氟甲硫基、二氟甲硫基、甲氧羰基、乙氧羰基、正或异丙氧羰基、正、异、仲或叔丁氧羰基或烯丙氧羰基,
R3特别优选代表甲基、乙基、正或异丙基、正、异、仲或叔丁基,或代表环丙基、环戊基或环己基,它们各自任选被氟、氯、甲基和/或乙基取代,
R4特别优选代表氢、甲基、乙基、正或异丙基、正、异、仲或叔丁基,或代表环丙基、环戊基或环己基,它们各自任选被氟、氯、甲基和/或乙基取代,
R5特别优选代表基团-Y-R6,其中
Y 代表下列基团之一:-CH2-、-CH(CH3)-、-CH2CH2-、-CH(C2H5)-、-CH(C3H7-i)-、-CHF-、-CH-Cl-或-CH(环丙基)-,
R6特别优选代表苯基或苯氧基,它们各自任选被相同或不同的取代基单至三取代,适合的取代基是氯、溴、硝基、氰基、甲基、乙基、正和异丙基、正、异、仲和叔丁基、甲氧基、乙氧基、正和异丙氧基、正、异、仲和叔丁氧基、甲硫基、三氟甲基、二氟甲基、三氟甲氧基、二氟甲氧基、三氟甲硫基、二氟甲硫基,和以及苯基或苯氧基,它们各自任选被相同或不同的下列取代基单至三取代:氯、溴、硝基、氰基、甲基、乙基、甲氧基、乙氧基、正或异丙氧基、正、异、仲或叔丁基、三氟甲基、三氟甲氧基、二氟甲氧基或三氟甲硫基。
R1非常特别优选代表甲基、乙基、异丙基、叔丁基、甲氧基甲基、1-氯-1-乙基或1-氟-1-乙基。
R2非常特别优选代表氢、氯、溴、氰基、硝基、甲氧羰基、乙氧羰基、异丙氧羰基或烯丙氧羰基。
R3非常特别优选代表甲基、乙基、异丙基、叔丁基或环丙基。
R4非常特别优选代表氢、甲基、乙基、异丙基或环丙基。
R5非常特别优选代表基团-Y-R6,其中
Y 代表下列基团之一:-CH2-、-CH(CH3)-或-CH2CH2-,
R6非常特别优选代表苯基或苯氧基,它们各任选被相同或不同的
取代基单或二取代,适合的取代基是氯、溴、硝基、氰基、甲基、
乙基、正和异丙基、正、异、仲和叔丁基、甲氧基、乙氧基、正和
异丙氧基、正、异、仲和叔丁氧基、三氟甲基、三氟甲氧基和二氟
甲氧基,和以及苯基或苯氧基,它们各任选被相同或不同的下列取
代基单至三取代:氯、溴、硝基、氰基、甲基、甲氧基、乙氧基、
正或异丙氧基、正、异、仲或叔丁氧基、三氟甲基、三氟甲氧基、
二氟甲氧基或三氟甲硫基。
在上面的一般术语或在优选范围中给出的基团定义和说明适用于终产品,且相应地适用于原料和中间体。这些基团的定义可以按需要相互间组合,即各自优选范围间的组合也是可以的。
优选的本发明式(I)化合物是那些含有上述优选含意组合的化合物。
特别优选的本发明式(I)化合物是那些含有上述特别优选含意组合的化合物。
非常特别优选的本发明式(I)化合物是那些含有上述非常特别优选含意组合的化合物。
在上下文所提到的基团的定义中,烃基基团如烷基或链烯基,以及与杂原子如烷氧基或烷硫基相连的烃基,在每种情况下,可以是其可能情况下的直链或支链。
制备式(I)化合物的上述方法(a)是在稀释剂存在下进行的。
可以采用的稀释剂是所有的常规溶剂。
可以优选采用下列溶剂:任选卤代的脂肪烃或芳烃、醚类或腈类,例如环己烷、甲苯、氯苯、氯仿、二氯甲烷、二氯乙烷、二噁烷、四氢呋喃、***或乙腈。
制备式(I)化合物的上述方法(a)是在碱存在下进行的。
可以在方法(a)中采用的碱是所有常用质子受体。可以优选采用下列碱:碱金属或碱土金属氢氧化物、碱金属或碱土金属碳酸盐、碱金属或碱土金属碳酸氢盐或含氮的碱。可以提到的实例是氢氧化钠、氢氧化钙、碳酸钾、碳酸氢钠、三乙胺、二苄基胺、二异丙基胺、吡啶、喹啉、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBN)和二氮杂二环十一碳烯。
在上述方法(a)中的反应温度可以相当宽的范围内变化。通常,该方法是在-40℃和+200℃间的温度下进行的,优选在0℃和100℃间的温度下。
当实施上述方法(a)制备式(I)化合物时,每摩尔的式(II)5-氨基吡唑通常采用l至2摩尔,优选1至1.5摩尔的式(III)酰基卤。
终产物用通常已知的方式处理和分离。
制备式(I)化合物的上述方法(b/α)是用卤化剂进行的。
所有的常规卤化剂均可能用于此目的。可以优选采用下列卤化剂:Cl2、Br2、次卤酸或其盐,例如,次氯酸钠、次氯酸钾、次溴酸钠和次溴酸钾,SO2Cl2、S2Cl2、PCl5或N-溴代琥珀酰亚胺。
如果需要,制备式(I)化合物的上述方法(b/α)是在稀释剂存在下进行的。可以优选采用下列稀释剂:任选卤代的脂肪烃或芳烃、醚类、腈类或酰胺类,例如环己烷、甲苯、氯苯、氯仿、二氯甲烷、二氯乙烷、二噁烷、四氢呋喃、***、乙腈或二甲基甲酰胺。
如果需要,制备式(I)化合物的上述方法(b/α)是在催化剂存在下进行的。可以采用的适合的催化剂是所有常规用于卤化反应的酸性或碱性催化剂,例如氢卤酸或乙酸钠,以及游离基引发剂如偶氮异丁腈或过氧化二苯甲酰。
在上述方法(b/α)中的反应温度可以相当宽的范围内变化。通常,该方法是在-40℃和+120℃间的温度下进行的,优选在0℃和80℃间的温度下。
当实施上述方法(b/α)制备式(I)化合物时,每摩尔的式(Ia)酰基化的5-氨基吡唑通常采用1至2摩尔,优选1至1.5摩尔的卤化剂。
终产物用通常已知的方式处理和分离。
制备式(I)化合物的上述方法(b/β)是用硝化剂进行的。
所有的常规硝化剂均可能用于此目的。可以优选采用下列硝化剂:硝酸,如果需要在硫酸、水、乙酸或乙酸酐中,在四氯甲烷中的N2O5,与BF3一块使用的硝酸甲酯,在三氟乙酸中的亚硝酸钠或N2O4。
如果需要,制备式(I)化合物的上述方法(b/β)是在稀释剂存在下进行的。可以优选采用下列稀释剂:任选卤代的脂肪烃如二氯甲烷、氯仿、四氯化碳或氯苯或硝基苯。
在上述方法(b/β)中的反应温度可以相当宽的范围内变化。通常,该方法是在0℃和100℃间的温度下进行的,优选在0℃和40℃间的温度下。
当实施上述方法(b/β)制备式(I)化合物时,每摩尔式(Ia)酰基化的5-氨基吡唑通常采用1至2摩尔,优选1至1.5摩尔的硝化剂。
终产物用通常已知的方式处理和分离。
用在制备方法(a)中的式(II)原料大部分是已知的(参见,例如《有机化学杂志》(J.Org.Chem.)1956,21,第1240页等和1964,29,第1915页等和《化学研究杂志》(J.Chem.Research)1993,第76页等),或可以通过已知的方法制备(参见,例如,上面的参考文献)。
R1、R3和R4具有上述含意。
新的式(IIa)5-氨基吡唑可以根据方法(b/α)如下获得:
R1、R3和R4具有上述含意,
在盐酸存在下,与氯化剂反应,优选与硫酰氯反应。
在制备方法(a)中用作另一种原料的式(III)的酰基卤是有机化学中的通常已知的化合物。在式(III)中Hal优选代表氯或溴。
在制备方法(b)中用作原料的式(Ia)是本发明的化合物,且可以根据制备方法(a)中给出的资料获得。
一些式(I)的酰基化的5-氨基吡唑也可以如下获得:
R1、R2、R3和R4具有上述含意,且
R7代表基团-Y-R8,其中
Y具有上述含意,且
R8代表卤代芳基、优选碘代或溴代苯基,特别优选4-碘代或溴代苯基,在碱如碳酸钾存在下和在稀释剂如甲苯存在下,优选在所用的溶剂的沸点温度下,与式(V)的硼酸反应
Ar-B(OH)2 (V)其中
Ar代表任选取代的苯基,适合的取代基优选、特别优选或非常特别优选为那些具有在式(I)化合物的描述中已经提到的为优选、特别优选或非常特别优选的R6取代基。
式(Ib)的物质可以通过例如根据本发明制备式(I)物质的方法来获得(参见制备实施例)。
式(V)的化合物是已知的和/或可以用已知的方法简单地制备。
本发明活性化合物适合防治动物害虫,优选防治节肢动物,特别是出现在农业、森林、贮藏产品和材料保护以及卫生方面的昆虫、蜱螨。它们对正常的敏感和抗性种类和对所有或某些生长发育阶段均有活性。上述害虫包括:等足纲,例如,潮虫(Oniscus asellus)、鼠妇(Armadillidium vulgare)和斑鼠妇(Porcellio scaber)。倍足目,例如,Blaniulus guttulatus。唇足目,例如,地蜈蚣(Geophilus carpophagus)和蚰蜒(Scutigeraspec)。综合目,例如,洁幺蚰(Scutigerella immaculata)。缨尾目,例如,西洋衣鱼(Lepisma saccharina)。弹尾目,例如,棘跳虫(Onychiurus armatus)。直翅目,例如,东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplanetaamericana)、马德拉蜚蠊(Leucophaea maderae)、德国小蠊(Blattellagermanica)、家蟋蟀(Acheta domesticus)、蝼蛄属(Gryllotalpa spp.)、亚洲飞蝗(Locusta migratoria)、殊种蚱蜢(Melanoplus differentialis)和沙漠蝗(Schistocerca gregaria)。革翅目,例如,欧洲球螋(Forficula auricularia)。等翅目,例如,犀白蚁属(Reticulitermes spp.)。虱目,例如,体虱(Pediculus humanus corporis)、血虱属(Haematopinusspp.)和颚虱属(Linognathus spp.)。食毛目,例如,啮毛虱属(Trichodectes spp.)和Damalinea spp.。缨翅目,例如,温室条蓟马(Hercinothrips femoralis)和棉蓟马(Thripstabaci)。半翅目,例如,扁盾蝽属(Eurygaster spp.)、中棉红蝽(Dysdercusintermedius)、甜菜拟网蝽(Piesma quadrata)、温带臭蝽(Cimexlectularius)、红腹猎蝽(Rhodnius prolixus)和锥蝽属(Triatoma spp.)。同翅目,例如,甘蓝粉虱(Aleurodes brassicae)、甘薯粉虱(Bemisiatabaci)、温室粉虱(Trialeurodes vaporariorum)、棉蚜(Aphis gossypii)、甘蓝蚜(Brevicoryne brassicae)、茶藨隐瘤蚜(Cryptomyzus ribis)、甜菜蚜(Aphis fabae)、苹果蚜(Aphis pomi)、苹果绵蚜(Eriosomalanigerum)、桃大尾蚜(Hyalopterus arundinis)、麦长管蚜(Macrosiphumavenae)、瘤额蚜属(Myzus spp.)、Phemigus spp.、忽布疣蚜(Phorodonhumili)、禾谷缢管蚜(Rhopalosiphum padi)、微叶蝉属(Empoascaspp.)、Euscelis bilobatus、黑尾叶蝉(Nephotettix cincticeps)、水土坚蚧(Lecanium corni)、油榄黑盔蚧(Saissetia oleae)、灰稻虱(Laodelphaxstriatellus)、稻褐飞虱(Nilaparvata lugens)、红园蚧(Aonidiellaaurantii)、夹竹桃园蚧(Aspidiotus hederae)、粉蚧属(Pseudococcus spp.)和木虱属(Psylla spp.)。鳞翅目,例如,棉红蛉虫(Pectinophora gossypiella)、松天蛾(Bupaluspiniarius)、冬尺蛾(Cheimatobia brumata)、Lithocolletis blancardella、苹果巢蛾(Hyponomeuta padella)、小菜蛾(Plutella maculipennis)、天幕毛虫(Malacosoma neustris)、黄毒蛾(Euproctis chrysorrhoea)、毒蛾属(Lymantria spp.)、棉潜蛾(Bucculatrix thurberiella)、桔潜叶蛾(Phyllocnistis citrella)、Agrotis spp.、Euxoa spp.、Feltia spp.、棉斑实蛾(Earias insulana)、棉铃虫属(Heliothis spp.)、甜菜夜蛾((Spodopteraexigua)、甘蓝夜蛾(Mamestra brassicae)、小眼夜蛾(Panolis flammea)、斜纹夜蛾(Prodenia litura)、粘虫属(Spodoptera spp.)、粉纹夜蛾(Trichoplusia ni)、苹蠹蛾(Carpocapsa pomonella)、粉蝶属(Pierisspp.)、禾草螟属(Chilo spp.)、Pyrausta nubilalis、Ephestiakuehniella、蜡螟(Galleria mellonella)、幕衣蛾(Tineola bisselliella)、袋衣蛾(Tinea pellionella)、褐织蛾(Hofmannophila pseudospretella)、Cacoecia podana、Capua reticulana、枞色卷蛾(Choristoneurafumiferana)、葡萄果蠹蛾(Clysia ambiguella)、茶长卷蛾(Homonamagnanima)和栎绿卷蛾(Tortrix viridana)。
鞘翅目,例如,具斑窃蠹(Anobium punctatum)、谷蠹(Rhizoperthadominica)、大豆象(Acanthoscelides obtectus)、家天牛(Hylotrupesbajulus)、赤杨紫跳甲(Agelasrtica alni)、马铃薯甲虫(Leptinotarsadecemlineata)、辣根猿叶甲(Phaedon cochleariae)、条叶甲属(Diabroticaspp.)、油菜蓝跳甲(Psylliodes chrysocephala)、墨西哥豆甲(Epilachnavarivestis)、隐翅甲属(Atomaria spp.)、锯谷盗(Oryzaephilussurinamensis)、花象甲属(Anthonomus spp.)、米象属(Sitophilus spp.)、葡萄黑耳喙象(Otiorrhynchus sulcatus)、香蕉根象甲(Cosmopolitessordidus)、甘蓝荚象甲(Ceuthorrhynchus assimilis)、苜蓿叶象虫(Hyperapostica)、皮蠹属(Dermestes spp.)、斑皮蠹属(Trogoderma spp.)、圆皮蠹属(Anthrenus spp.)、毛蠹属(Attagenus spp.)、粉蠹属(Lyctus spp.)、油菜花露尾甲(Meligethes aeneus)、蛛甲属(Ptinus spp.)、金黄蛛甲(Niptus hololeucus)、裸蛛甲(Gibbium psylloides)、拟谷盗属(Triboliumspp.)、黄粉虫(Tenebrio molitor)、Agriotes spp.、Conoderus spp.、鳃角金龟(Melolontha melolontha)、六月金龟(Amphimallon sostitialis)和Costelytra zealandica。膜翅目,例如锯角叶蜂属,叶蜂属,蚁尾属,厕蚁和胡蜂属。双翅目,例如,伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culex spp.)、黄猩猩果蝇(Drosophila melanogaster)、蝇属(Muscaspp.)、厕蝇属(Fannia spp.)、红头丽蝇(Callophora erythrocephala)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyia spp.)、疽蝇属(Cuterebraspp.)、胃蝇属(Gastrophilus spp.)、Hyppobosca spp.、赫蝇属(Stomoxysspp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypoderma spp.)、虻属(Tabanusspp.)、Tannia spp.、Bibio hortulanus、瑞典麦杆蝇(Oscinella frit)、Phorbia spp.、菠菜潜叶花蝇(Pegomyia hyoscyami)、地中海实蝇(Ceratitiscapitata)、油榄实蝇(Dacus oleae)和沼泽大蚊(Tipula paludosa)。蚤目,例如,印鼠客蚤(Xenopsylla cheopis)和毛列蚤属(Ceratophyllusspp.)。蛛形纲,例如,蝎(Scorpio maurus)和毒寇蛛(Latrodectus mactans)。蜱螨目,例如,粗脚粉螨(Acarus siro)、隐喙蜱属(Argas spp.)、钝喙蜱属(Ornithodoros spp.)、鸡皮刺螨(Dermanyssus gallinae)、茶藨瘿螨(Eriophyes ribis)、柑桔锈螨(Phyllocoptruta oleivora)、牛蜱属(Boophilusspp.)、扇头蜱属(Rhipicephalus spp.)、花蜱属(Amblyomma spp.)、玻眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、瘙螨属(Psoroptesspp.)、皮螨属(Chorioptes spp.)、疥螨属(Sarcoptes spp.)、跗线螨属(Tarsonemus spp.)、苜蓿苔螨(Bryobia praetiosa)、全爪螨属(Panonychusspp.)和叶螨属(Tetranychus spp.)。
本发明活性化合物的突出之处在于其强的杀虫和杀螨活性。
具体地说,本发明式(I)化合物具有突出的杀虫活性。当用于叶面和土中栖生的昆虫时,它们显示出强的活性,例如对辣根猿叶甲(Phaedoncochleariae)、对小菜蛾(Plutella maculipennis)幼虫和对草地贪叶蛾(Spodoptera frugiperda)的幼虫,以及对黑尾叶蝉(Nephotettixcincticeps)有强的活性。
活性化合物可以转化成常规剂型,如溶液、乳剂、悬浮剂、粉剂、尘剂、膏剂、可溶性粉剂、颗粒剂、悬乳剂、用活性化合物浸渍的天然和合成物质和在用聚合物制成的微胶囊。
这些型剂可以用已知的方式生产,例如,将活性化合物与填充剂,即液体溶剂和/或与固体载体混合,并任选使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。
用水作填充剂的情况下,也可以用有机溶剂作助溶剂。作为液体溶剂,适合的主要有:芳族化合物,如二甲苯,甲苯或烷基萘,氯代芳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、矿物和植物油,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。
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:锯木屑、椰壳、玉米穗轴和烟茎;适合的乳化剂和/或起泡剂是: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,木素亚硫酸废液和甲基纤维素。
制剂中可以使用粘合剂如粉状、颗粒或乳胶形式的羧甲基纤维素和天然和合成聚合物,如***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。
也可能使用染料,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、钼和锌盐。
制剂中通常含有按重量计0.1至95%的活性化合物,优选0.5至90%。
本发明活性化合物可以其市售制剂和由这些制剂制备的使用形式存在,所述的制剂为与如下的其它活性化合物的混合物:杀虫剂、引诱剂、不育剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂或除草剂。杀虫剂包括例如磷酸酯类、氨基甲酸酯、羧酸酯类、氯代烃类、苯基脲类、由微生物生产的物质,及其它。
在混合物的特别有利的组分是例如下列: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-甲酰苯胺;2,6-二氯-N-(4-三氟甲基苯甲基)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-氧基]苯基}-3-甲氧基丙烯酸甲酯;(E)-甲氧基亚氨基[α-(邻甲苯氧基)-邻甲苯基]乙酸甲酯;2-苯基苯酚(OPP)、aldimorph、氨丙磷酸、敌菌灵、戊环唑、苯霜灵、碘萎灵、苯菌灵、乐杀螨、联苯、双苯***醇、灭瘟素、糠菌唑、磺酸丁嘧啶、丁赛特、石硫合剂、敌菌丹、克菌丹、多菌灵、萎锈灵、甲基克杀螨、地茂散、氯化苦、百菌清、乙菌利、硫杂灵、霜脲氰、环唑醇、酯菌胺、防霉酚、苄氯***醇、抑菌灵、哒菌清、氯硝胺、乙霉威、噁醚唑、甲嘧醇、烯酰吗啉、烯唑醇、清螨普、二苯胺、吡菌硫、灭菌磷、二噻农、十二烷胍、腙菌酮、克菌散、环氧唑(epoxyconazole)、乙嘧啶、氯唑灵、双氯苯嘧啶、苯氰唑、一甲呋萎灵、种衣酯、拌种咯、苯锈啶、丁苯吗啉、乙酸三苯基锡、三苯羟基锡、福美铁、嘧菌腙、氟啶胺、fludioxonil、氟氯菌核利、fluquinconazole、氟哇唑、磺菌胺、氟酰胺、粉唑醇、灭菌丹、乙磷铝、四氯苯酞、麦穗宁、呋霜灵、拌种胺、双胍辛、六氯苯、己唑醇、甲羟异噁唑、抑霉唑、酰胺唑、双胍辛醋酸盐、异稻瘟净、异菌脲、稻瘟灵、春日霉素、铜制剂如氢氧化铜、环烷酸铜、碱式氯化铜、硫酸铜、氧化铜、喹啉酮和波尔多混合物、双代混剂、代森锰锌、代森锰、嘧菌胺、灭锈胺、甲霜灵、metconazole、磺菌威、担菌胺、代森联、噻菌胺、腈菌唑、福美镍、异丙消、氟苯嘧啶醇、甲呋酰胺、噁酰胺、oxamocarb、氧化萎锈灵、perfurazoat、戊菌唑、戊菌隆、稻病磷、匹马菌素、哌啶宁、多氧霉素、烯丙异噻唑、咪鲜安、二甲菌核利、霜霉威、丙环唑、甲基代森锌、定菌磷、啶斑肟、pyrimethanil、咯喹酮、五氯硝基苯、硫磺和硫制剂、戊唑醇、酞枯酸、四氯硝基苯、氟醚唑、噻菌灵、噻菌腈、甲基托布津、福美双、甲基立枯灵、对甲抑菌灵、***酮、***醇、唑菌嗪、杨菌胺、三环唑、环吗啉、氟菌唑、嗪氨灵、triticonazole、稻纹散、烯霜苄唑、代森锌、福美锌。杀细菌剂:
拌棉酚、防霉酚、氯定、福美镍、春日霉素、异噻菌酮、呋喃羧酸、土霉素、烯丙异噻唑、链霉素、酞枯酸、硫酸铜和其它铜制剂。杀虫剂/杀螨剂/杀线虫剂:
齐墩螨素、AC 303 630、乙酰甲胺磷、氟酯菊酯、棉铃威、涕灭威、甲体氯氰菊酯、双甲脒、齐墩螨素(avermectin)、AZ 60541、azadirachtin、乙基谷硫磷、谷硫磷、***锡、苏芸金杆菌、4-溴-2-(4-氯苯基)-1-(乙氧基甲基)-5-(三氟甲基)-1H-吡唑-3-腈、苯恶威、丙硫克百威、杀虫磺、乙体氟氯氰菊酯、联苯菊酯、丁苯威、溴醚菊酯(brofenprox)、溴硫磷、混戊威、噻嗪酮、丁酮威、丁基哒螨酮、硫线磷、西维因、克百威、三硫磷、丁硫克百威、巴丹、除线威、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-乙酰亚胺(ethanimid)酰胺、毒死蜱、甲基毒死蜱、顺式苄呋菊酯、三氟氯氰菊酯、四螨嗪、杀螟腈、乙氰菊酯、氟氯氰菊酯、氯氟氰菊酯、三环锡、氯氰菊酯、灭蝇胺、溴氰菊酯、甲基内吸磷、内吸磷、异吸磷II、杀螨隆、地亚农、氯线磷、敌敌畏、dicliphos、百治磷、乙硫磷、伏虫脲、乐果、甲基毒虫畏、二噁硫磷、乙拌磷、克瘟散、emamectin、高氰戊菊酯、除蚜威、乙硫磷、醚菊酯、丙线磷、乙嘧硫磷、克线磷、喹螨醚、螨完锡、杀螟硫磷、仲丁威、苯硫威、双氧威、甲氰菊酯、fenpyrad、唑螨酯、倍硫磷、氰戊菊酯、锐劲特(fipronil)、氟啶胺、fluazuron、氟螨脲、氟氰戊菊酯、氟虫脲、氟醚菊酯(flufenprox)、氟胺氰菊酯、地虫硫磷、安果、噻唑硫磷、溴醚菊酯(fubfenprox)、呋线威、六六六、庚虫磷、氟铃脲、噻螨酮、咪蚜胺、异稻瘟净、氯唑磷、异丙胺磷、异丙威、噁唑磷、伊维菌素、λ-三氟氯氰菊酯、lufenuron、马拉硫磷、灭蚜硫磷、速灭磷、倍硫磷亚砜、蜗牛敌、虫螨畏、甲胺磷、甲噻硫磷、甲硫威、灭多威、速灭威、米尔倍菌素、久效磷、moxidectin、二溴磷、NC184、NI25、nitenpyram、氧乐果、草肟威、砜吸硫磷、异砜磷、对硫磷、甲基对硫磷、氯菊酯、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、辛硫磷、抗蚜威、甲基嘧啶硫磷、嘧啶硫磷、丙溴磷、甲丙威、丙虫威、残杀威、低毒硫磷、发果、pymetrozin、pyrachlophos、吡唑硫磷、苯哒嗪硫磷、反灭菊酯、除虫菊、哒螨酮、pyrimidifen、蚊蝇醚、喹硫磷、RH 5992、水杨硫磷、硫线磷、silafluofen、治螟磷、甲丙硫磷、tebufenozide、tebufenpyrad、特丁嘧啶硫磷、伏虫隆、七氟菊酯、双硫磷、叔丁威、特丁甲拌磷、杀虫畏、thiafenox、硫双灭多威、己酮肟威、甲基乙拌磷、喹线磷、苏芸金菌素、四溴菊酯、苯赛螨、***磷、triazuron、敌百虫、杀虫隆、trimethacarb、完灭硫磷、二甲威、二甲苯威、YI5301/5302、zetamethrin。
与其它已知的活性化合物如除草剂,或与化肥和生长调节剂的混合物也是可能的。
此外,本发明活性化合物可以以带有增效剂混合物的形式存在于其市售制剂和由这些制剂制备的使用形式中。增效剂是可以增加活性化合物活性,而所添加的增效剂本身无需有活性的化合物。
由市售制剂制备的使用形式中的活性化合物的含量可以在相当宽的范围内变化。使用形式的活性化合物浓度可以是按重量计0.0000001至95%的活性化合物,优选在按重量计0.00001至1%间。
使用形式是以适合之的常规形式采用的。
当防治卫生和贮藏产品方面的害虫时,活性化合物的突出之处在于其在木材和陶土上的显著残留作用和对石灰处理过的底物上的碱的良好的稳定性。
再则,业已发现,本发明的式I化合物对破坏工业材料的昆虫具有强的杀虫活性。
可以列举且是优选的昆虫是下列,但不限于这些昆虫:甲虫如家天牛(Hylotrupes bajulus)、Chlorophorus pilosis、具斑窃蠹(Anobiumpunctatum)、Xestobium rufovillosum、Ptilinus pecticornis、Dendrobium pertinex、Ernobium mollis、Priobium carpini、褐粉蠹(Lyctus brunneus)、非洲粉蠹(L.africanus)、平颈粉蠹(L.planicollis)、桴粉蠹(L.linesris)、L.pubescens、Trogoxylonaequale、鳞毛粉蠹(Minthes rugicollis)、小蠹(Xyleborus spec.)、Tryptodendron spec.、咖啡黑长蠹(Apate monachus)、槲长蠹(Bostyrchuscapucins)、Heterobostrychus brunneus、Sinoxylon spec.、竹长蠹(Dinoderus minutus)。革翅目,如小钢青树蜂(Sirex juvencus)、大树蜂(Urocerus gigas)、U.gigastaignus、U.augur。白蚁,如木白蚁(Kalotermes flavicollis)、隐白蚁(Cryptotermes brevis)、灰点异白蚁(Heterotermes indicola)、黄胸散白蚁(Reticulitermes flavipes)、R.santonecsis、R.lucifugus、澳洲白蚁(Mastotermes darwiniensis)、Zootermopsis nevadensis、家白蚁(Coptotermes formosanus)。衣鱼如西洋衣鱼(Lepisma saccharina)。
在本文中,工业材料应理解为无生命的材料如优选的是聚合物、胶水、粘性材料、纸和板、皮革、木材和衍生的木制品和漆。
可以用本发明的药剂或含有之的组合物保护的木材和衍生的木制品应理解为,例如,建筑木料、木梁、铁道枕木、桥梁组件、突堤、木车、盒、箱、容器、电线杆、木质矿道顶木、木制的门窗、胶合板、碎料板、木工的制品、或通常用在建筑或细木工中的木制品。
本发明活性化合物可以以其原样、以其浓缩物或通常的常规制剂使用。所述的常规制剂是例如粉剂、颗粒剂、溶液、悬浮剂、乳剂或膏剂。
上述制剂可以以本身已知的方式制备,例如通过将活性化合物与至少一种溶剂或稀释剂、乳化剂、分散剂和/或粘合剂或固定剂、防水剂、如果需要脱水剂和UV稳定剂和如果需要着色剂和染料和其它加工辅助剂混合。
用于保护木材和木制品的杀虫组合物或浓缩物包含浓度为按重量计0.0001至95%,特别是按重量计0.001至60%的活性化合物。
所采用的药剂或浓缩物的量取决于昆虫的种类和密度,以及介质。所用最佳量可以在每种情况下由一系列试验来确定。然而,一般而言,以所要保护的材料为基准,采用按重量计0.0001至20%,优选按重量计0.001至10%的活性化合物已足矣。
所用的溶剂和/或稀释剂是有机化学溶剂或溶剂混合物和/或低挥发性的油性或油样溶剂或溶剂混合物和/或极性有机化学溶剂和溶剂混合物和/或水,且如果适宜是乳化剂和/或润湿剂。
所用的有机化学溶剂优选是油性或油样溶剂,所述的溶剂具有大于35的挥发度(evaporation number)和高于30℃的闪点,优选高于45℃。用作这种油性或油样溶剂的物质是低挥发性的,且不溶于水,这类物质适合的有矿物油或其芳族馏份且含有矿物油的溶剂混合物,优选是石油溶剂、石油和/或烷基苯。
使用沸程为170到220℃的矿物油、沸程为170到220℃的石油溶剂、沸程为250到350℃的碇子油、沸程为160到280℃的石油或芳族化合物及松节油等是有利的。
在优选的实施方案中,所用的物质是沸程为180至210℃的液体脂族烃或沸程为180至220℃的芳族烃和脂族烃的高沸点混合物和/或碇子油和/或单氯萘,优选α-单氯萘。
挥发度高于35且闪点高于30℃,优选高于45℃的低挥发性有机油性或油样溶剂,可以部分地由低或中挥发性的有机化学溶剂替代,其前提条件是,溶剂混合物也具有高于35的挥发度且闪点高于30℃,优选高于45℃,且杀虫剂/杀真菌剂混合物在此溶剂混合物中是可溶的或可乳化的。
在优选的实施方案中,部分有机化学溶剂或溶剂混合物或脂族极性有机化学溶剂或溶剂混合物被替代。优选采用的物质是含有羟基和/或酯和/或醚基团的脂族有机化学溶剂,如例如乙二醇醚、酯等。
在本发明范围内使用的有机化学粘合剂是本身已知的粘合干性油和/或合成树脂,它们可以用水稀释和/或在所采用的有机化学溶剂中是可溶的、可分散的或可乳化的,特别是那些由如下组成,或包含如下成分的粘合剂:丙烯酸树酯、乙烯树脂,例如聚乙酸乙烯酯、聚酯树酯、缩聚或加聚树脂、聚氨酯树脂、醇酸树脂或改性的醇酸树脂、酚树脂、烃类树脂如茚-香豆酮树脂、硅氧烷树脂、干性植物油和/或干性油和/或以天然和/或合成树脂为基础的物理干性粘合剂。
用作粘合剂的合成树脂可以以乳液、分散液或溶液的形式使用。沥青或沥青状物质也可以用作粘合剂的物质,其量至多为按重量计10%。此外,可以采用特别是本身已知的着色剂、染料、防水剂、添味剂和抑制剂或抗腐蚀剂。
根据本发明,组合物或浓缩物优选含有至少一种醇酸树脂或改性醇酸树脂和/或干性植物油作为有机化学粘合剂。根据本发明所优选采用的物质是油含量超过按重量计45%,优选50至68%的醇酸树脂。
所有的或部分上述粘合剂可以由固定剂(混合物)或增塑剂(混合物)替代。这些添加剂是旨在防止活性化合物挥发和结晶或沉淀。它们优选替代0.01至30%的粘合剂(以所用的粘合剂的100%为基准)。
增塑剂来自属于下列化学分类的物质:邻苯二甲酸酯类,如邻苯二甲酸二丁酯、邻苯二甲酸二辛酯或邻苯二甲酸苄基丁基酯,磷酸酯类,如磷酸三丁酯,己二酸酯类,如二(2-乙基己基)己二酸酯,硬脂酸酯,如硬脂酸丁酯或硬脂酸戊酯,油酸酯类,如油酸丁酯,甘油醚类或高分子量乙二醇醚类、甘油酯类和对甲苯磺酸酯类。
固定剂化学上基于聚乙烯基烷基醚类如聚乙烯基甲基醚,或酮类如二苯甲酮或亚乙基二苯甲酮。
另一种适合的溶剂或稀释剂是(特别是)水,如果适宜是水与一或多种上述有机化学溶剂或稀释剂、乳化剂和分散剂的混合物。
特别有效的木材保护通过工业规模的浸渍工艺,例如真空、双真空或压力工艺的方式获得。
如果适宜,直接可用的组合物可以包含其它杀虫剂和如果适宜也可以有一或多种杀真菌剂。
可能混合于其中的另外的组分优选是WO 94/29 268中提到的杀虫剂和杀真菌剂。在上述文献中提到的化合物明确地说是本发明申请的一部分。
可以非常特别优选地混合于其中的组分是杀虫剂如毒死蜱、辛硫磷、silafluofin、氟氯氰菊酯、甲体氯氰菊酯、氯氰菊酯、溴氰菊酯、氯菊酯、咪呀胺、NI-25、氟虫脲、氟铃脲和杀虫隆,以及杀真菌剂如环氧唑(epoxyconazole)、己唑醇、戊环醇、丙环唑、戊唑醇、环唑醇、metconazole、抑霉唑、苯氟磺胺、甲苯氟磺胺、3-碘代-2-丙炔基丁基氨基甲酸酯、N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
在室温下,将0.47g(0.006mol)吡啶加入0.99g(0.005mol)5-氨基-4-乙氧羰基-3-乙基-1-甲基吡唑的80ml二氯甲烷溶液中。随后在相同的温度下,滴加入1.11g(0.006mol)4-甲氧基苯基乙酰氯的20ml二氯甲烷溶液。将此混合物在室温下搅拌过夜,并随后回流搅拌24小时。当冷却时,将反应混合物用稀HCl和用稀NaHCO3水溶液洗涤。有机相经MgSO4干燥,过滤并蒸发至干燥。
在室温下,将0-95g(0.012mol)吡啶加入1.25g(0.01mol)5-氨基-3-乙基-1-甲基吡唑的120ml二氯甲烷溶液中。随后在相同的温度下,滴加入3.37g(0.012mol)4-(4-氯苯氧基)苯基乙酰氯的30ml二氯甲烷溶液。此混合物在室温下搅拌过夜后,依次用稀HCl和用稀NaHCO3水溶液洗涤,产物经MgSO4干燥,过滤并蒸发至干燥。
如此给出3.10g(理论值的84%)的5-(4-(4-氯苯氧基)苯基乙酰氨基)-3-乙基-1-甲基吡唑,为棕色油状物。1H NMR(CDCl3):δ=1.19、2.57、3.56、3.63、3.73、6.04、6.92-7.03、7.27-7.33ppm。实施例3(方法b/α)
在0℃下,将037g(0.00275mol)硫酰氯滴加入0.92g(0.0025mol)5-(4-(4-氯苯氧基)苯基乙酰氨基)-3-乙基-1-甲基吡唑(实施例2)的10ml二氯甲烷溶液中。此混合物在室温下搅拌过夜后,用10ml二氯甲烷稀释,并依次用水、饱和NaHCO3水溶液和饱和NaCl水溶液洗涤,经MgSO4干燥,过滤并蒸发至干燥。
如此给出0.80g(理论值的79%)的4-氯-5-(4-(4-氯苯氧基)苯基乙酰氨基)-3-乙基-1-甲基吡唑,为棕色油状物。1H NMR(CDCl3):δ=1.21、2.57、3.63、3.77、6.82、6.92-7.04、7.30-7.35ppm。实施例4(万法b/α)
在0℃下,将0.44g(0.00275mol)溴滴加入0.92g(0.0025mol)5-(4-(4-氯苯氧基)苯基乙酰氨基)-3-乙基-1-甲基吡唑(实施例2)的10ml二氯甲烷溶液中。此混合物在室温下搅拌过夜后,用10ml二氯甲烷稀释,并依次用水、饱和NaHCO3水溶液和饱和NaCl水溶液洗涤,经MgSO4干燥,过滤并蒸发至干燥。
如此给出0.90g(理论值的80%)的4-溴-5-(4-(4-氯苯氧基)苯基乙酰氨基)-3-乙基-1-甲基吡唑,为棕色油状物。1H NMR(CDCl3):δ=1.20、2.56、3.66、3.77、6.80、6.91-7.04、7.27-7.36ppm。实施例5(方法a)
在室温下,将1.90g(0.024mol)吡啶加入3.19g(0.02mol)5-氨基-4-氯-3-乙基-1-甲基吡唑(实施例IV-1)的120ml二氯甲烷溶液中。随后在相同的温度下,滴加入5.60g(0.024mol)4-溴苯基乙酰氯的30ml二氯甲烷溶液。此混合物在室温下搅拌过夜后,之后依次用稀HCl和用稀NaHCO3水溶液洗涤。有机相经MgSO4干燥,过滤并蒸发至干燥。
如此给出4.61g(理论值的63%)的5-(4-溴苯基乙酰基)氨基-4-氯-3-乙基-1-甲基吡唑,为无色固体,熔点167-168℃。式(IV)原料的制备实施例(IV-1)
在室温下,将14.85g(0.11mol)硫酰氯滴加入12.5g(0.1mol)5-氨基-3-乙基-1-甲基吡唑的100ml 20%浓度的HCl溶液中。将此混合物在60℃下搅拌40小时。在加入7.43g(0.055mol)硫酰氯后,将混合物在60℃下再搅拌6小时。在加入2.97g(0.022mol)硫酰氯并在60℃下再搅拌18小时后,将混合物用水处理,用稀NaOH将pH调至9,并将混合物用***反复萃取。合并的有机相经MgSO4干燥,过滤并蒸发至干燥。
如此给出13.47g(理论值的84%)的5-氨基4-氯-3-乙基-1-甲基吡唑,为淡黄色固体,熔点50-51℃。
应用实施例
实施例A
被服猿叶甲幼虫试验
溶剂: 7份重量的二甲基甲酰胺
乳化剂: 1份重量的烷芳基聚乙二醇醚
制备活性化舍物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该浓液用水稀释至所需浓度。
将甘蓝叶(Brassica oleracea)通过浸入所需浓度的活性化合物制剂中来处理,当叶片仍润湿时,放上辣根猿叶甲(Phaebon cochleariae)幼虫。
经过了所需的时间后,确定杀死%。100%是指所有的甲虫幼虫均被杀死;O%是指没有甲虫幼虫被杀死。
在此试验中,在实验活性化合物浓度为0.1%的条件下,7天后杀死100%的制备例化合物有例如下列:2、3、9、10、11、12、13、15、16、29、31和32。实施例B小菜蛾试验溶剂: 7份重量的二甲基甲酰胺乳化剂: 1份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该浓液用水稀释至所需浓度。
将甘蓝叶(Brassica oleracea)通过浸入所需浓度的活性化合物制剂中来处理,当叶片仍润湿时,放上小菜蛾(Plutella maculipennis)幼虫。
经过了所需的时间后,确定杀死%。100%是指所有的毛虫均被杀死;0%是指没有毛虫被杀死。
在此试验中,在实验活性化合物浓度为0.1%的条件下,7天后杀死100%的制备例化合物有例如下列:2、3、12、13、15、16、29、31和32。实施例C草地贪夜蛾试验溶剂:7份重量的二甲基甲酰胺乳化剂:1份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该浓液用水稀释至所需浓度。
将甘蓝叶(Brassica oleracea)通过浸入所需浓度的活性化合物制剂中来处理,当叶片仍润湿时,放上草地贪夜蛾(Spodoptera frugiperda)毛虫。
经过了所需的时间后,确定杀死%。100%是指所有的毛虫均被杀死;0%是指没有毛虫被杀死。
在此试验中,在实验活性化合物浓度为0.1%的条件下,7天后杀死100%的制备例化合物有例如下列:2、6、13、15、16、31和32。实施例D黑尾叶蝉试验溶剂:7份重量的二甲基甲酰胺乳化剂:1份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该浓液用水稀释至所需浓度。
将稻秧(Oryza sativa)通过浸入所需浓度的活性化合物制剂中来处理,当叶片仍润湿时,放上黑尾叶蝉(Nephotettix cincticeps)毛虫。
经过了所需的时间后,确定杀死%。100%是指所有的黑尾叶蝉均被杀死;0%是指没有黑尾叶蝉被杀死。
在此试验中,在实验活性化合物浓度为0.1%的条件下,6天后杀死至少90%的制备例化合物有例如下列:13、29、31和32。
Claims (10)
2.根据权利要求1的式(I)化合物,其中
R1代表C1-C4-烷基、C1-C4-烷氧基-C1-C4-烷基或C1-C4-卤代烷基,
R2代表氢、卤素、氰基、硝基、三氟甲硫基、二氟甲硫基、C1-C4-烷氧羰基或C2-C4-链烯氧羰基,
R3代表C1-C4-烷基,或代表C3-C6-环烷基,该环烷基任选被卤素或C1-C4-烷基取代,
R4代表氢、C1-C4-烷基,或代表C3-C6-环烷基,该环烷基任选被卤素或C1-C4-烷基取代,且
R5代表基团-Y-R6,其中
Y 代表C1-C4-烷二基,该烷二基任选被卤素或C3-C6-环烷基取代,
和
R6代表苯基或苯氧基,它们各任选被相同或不同的取代基单至三
取代,适合的取代基是卤素、硝基、氰基、C1-C12-烷基、C1-C12-
烷氧基、C1-C12-烷硫基、C1-C12-卤代烷基、C1-C12-卤代烷氧
基、C1-C12-卤代烷硫基、C2-C12-链烯基、C1-C12-烷氧基-C2-
C12-链烯基、C1-C4-烷硫基-C2-C12-链烯基、C2-C12-卤代链烯
基,和以及苯基、苯氧基、苯硫基或苄基,它们各任选被相同或不
同的下列基团单至三取代:卤素、硝基、氰基、C1-C4-烷基、C1-
C4-烷氧基、C1-C4-烷硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基
或C1-C4-卤代烷硫基。
3.根据权利要求1的式(I)化合物,其中
R1代表甲基、乙基、正或异丙基、或正、异、仲或叔丁基,或代表甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、三氟甲基、二氟甲基、氟甲基、1-氯-1-乙基或1-氟-1-乙基,
R2代表氢、氟、氯、溴、氰基、硝基、三氟甲硫基、二氟甲硫基、甲氧羰基、乙氧羰基、正或异丙氧羰基、正、异、仲或叔丁氧羰基或烯丙氧羰基,
R3代表甲基、乙基、正或异丙基、正、异、仲或叔丁基,或代表环丙基、环戊基或环己基,它们各任选被氟、氯、甲基和/或乙基取代,
R4代表氢、甲基、乙基、正或异丙基、正、异、仲或叔丁基,或代表环丙基、环戊基或环己基,它们各任选被氟、氯、甲基和/或乙基取代,
R5代表基团-Y-R6,其中
Y 代表下列基团之一:-CH2-、-CH(CH3)-、-CH2CH2-、-CH(C2H5)-、-CH(C3H7-i)-、-CHF-、-CHCl-或-CH(环丙基)-,
R6代表苯基或苯氧基,它们各任选被相同或不同的取代基单至三取代,适合的取代基是氯、溴、硝基、氰基、甲基、乙基、正和异丙基、正、异、仲和叔丁基、甲氧基、乙氧基、正和异丙氧基、正、异、仲和叔丁氧基、甲硫基、三氟甲基、二氟甲基、三氟甲氧基、二氟甲氧基、三氟甲硫基、二氟甲硫基,和以及苯基或苯氧基,它们各任选被相同或不同的下列取代基单至三取代:氯、溴、硝基、氰基、甲基、乙基、甲氧基、乙氧基、正或异丙氧基、正、异、仲或叔丁氧基、三氟甲基、三氟甲氧基、二氟甲氧基或三氟甲硫基。
4.根据权利要求1的式(I)化合物,其中
R1代表甲基、乙基、异丙基、叔丁基、甲氧基甲基、1-氯-1-乙基或1-氟-1-乙基,
R2代表氢、氯、溴、氰基、硝基、甲氧羰基、乙氧羰基、异丙氧基羰基或烯丙氧羰基,
R3代表甲基、乙基、异丙基、叔丁基、或环丙基,
R4代表氢、甲基、乙基、异丙基或环丙基,
R5代表基团-Y-R6,其中
Y 代表下列基团之一:-CH2-、-CH(CH3)-或-CH2CH2-,
R6代表苯基或苯氧基,它们各任选被相同或不同的取代基单或二取代,适合的取代基是氯、溴、硝基、氰基、甲基、乙基、正和异丙基、正、异、仲和叔丁基、甲氧基、乙氧基、正和异丙氧基、正、异、仲和叔丁氧基、三氟甲基、三氟甲氧基和二氟甲氧基,和以及苯基或苯氧基,它们各任选被相同或不同的下列取代基单至三取代:氯、溴、硝基、氰基、甲基、甲氧基、乙氧基、正或异丙氧基、正、异、仲或叔丁氧基、三氟甲基、三氟甲氧基、二氟甲氧基或三氟甲硫基。
6.式(IIa)化合物其中
R1、R3和R4具有权利要求1中给出的含意。
7.农药,其特征在于,所述的农药包含至少一种权利要求1的式(I)化合物。
8.权利要求1的式(I)化合物防治害虫的应用。
9.防治害虫的方法,其特征在于,使权利要求1的式(I)化合物作用于害虫和/或其环境或作用于杂草和/或其环境。
10.制备农药的方法,其特征在于,将权利要求1的式(I)化合物与增充剂和/或乳化剂混合。
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DE19500789A DE19500789A1 (de) | 1995-01-13 | 1995-01-13 | Acylierte 5-Aminopyrazole |
DE19500789.1 | 1995-01-13 |
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CN95197297A Pending CN1172479A (zh) | 1995-01-13 | 1995-12-28 | 酰基化的5-氨基吡咯 |
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US (3) | US5843978A (zh) |
EP (1) | EP0802907A1 (zh) |
JP (1) | JPH10511968A (zh) |
CN (1) | CN1172479A (zh) |
AU (1) | AU700059B2 (zh) |
BR (1) | BR9510145A (zh) |
DE (1) | DE19500789A1 (zh) |
HU (1) | HU221736B1 (zh) |
WO (1) | WO1996021653A1 (zh) |
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US6316522B1 (en) * | 1997-08-18 | 2001-11-13 | Scimed Life Systems, Inc. | Bioresorbable hydrogel compositions for implantable prostheses |
DE19838708A1 (de) | 1998-08-26 | 2000-03-02 | Bayer Ag | Verwendung von 5-Amino-pyrazol-Derivaten zur Bekämpfung von Mikroorganismen |
AU2001290258A1 (en) * | 2000-09-22 | 2002-04-02 | Nihon Nohyaku Co. Ltd. | N-(4-pyrazolyl)amide derivatives, chemicals for agricultural and horticultural use, and usage of the same |
US7297660B2 (en) | 2001-03-28 | 2007-11-20 | Huntsman Petrochemical Corporation | Alkylene carbonate adjuvants |
WO2002094793A1 (de) * | 2001-05-23 | 2002-11-28 | Basf Aktiengesellschaft | Acylierte 4-aminopyrazole |
US7335779B2 (en) * | 2002-03-08 | 2008-02-26 | Quonova, Llc | Modulation of pathogenicity |
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JPH07106964B2 (ja) * | 1987-01-14 | 1995-11-15 | 株式会社トクヤマ | 摘果剤 |
JPS6425763A (en) * | 1987-04-24 | 1989-01-27 | Mitsubishi Chem Ind | Pyrazoles and insecticide and acaricide containing said pyrazoles as active ingredient |
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JPH0217187A (ja) * | 1988-07-06 | 1990-01-22 | Kumiai Chem Ind Co Ltd | フェノキシプロピオン酸アミド誘導体及び除草剤 |
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US5556873A (en) * | 1993-02-24 | 1996-09-17 | Rhone-Poulenc Inc. | Pesticidal 1-aryl-5-(substituted alkyl (thio) amido)pyrazoles |
US5656629A (en) * | 1995-03-10 | 1997-08-12 | Sanofi Winthrop, Inc. | 6-substituted pyrazolo (3,4-d)pyrimidin-4-ones and compositions and methods of use thereof |
-
1995
- 1995-01-13 DE DE19500789A patent/DE19500789A1/de not_active Withdrawn
- 1995-12-28 JP JP8521405A patent/JPH10511968A/ja not_active Ceased
- 1995-12-28 WO PCT/EP1995/005148 patent/WO1996021653A1/de active Application Filing
- 1995-12-28 BR BR9510145A patent/BR9510145A/pt not_active Application Discontinuation
- 1995-12-28 US US08/875,060 patent/US5843978A/en not_active Expired - Fee Related
- 1995-12-28 AU AU44350/96A patent/AU700059B2/en not_active Ceased
- 1995-12-28 HU HU9800485A patent/HU221736B1/hu not_active IP Right Cessation
- 1995-12-28 CN CN95197297A patent/CN1172479A/zh active Pending
- 1995-12-28 EP EP95943219A patent/EP0802907A1/de not_active Withdrawn
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1998
- 1998-09-02 US US09/145,532 patent/US5981566A/en not_active Expired - Fee Related
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EP0802907A1 (de) | 1997-10-29 |
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US5843978A (en) | 1998-12-01 |
JPH10511968A (ja) | 1998-11-17 |
BR9510145A (pt) | 1997-12-30 |
HUT77558A (hu) | 1998-06-29 |
HU221736B1 (hu) | 2002-12-28 |
US6100288A (en) | 2000-08-08 |
DE19500789A1 (de) | 1996-07-18 |
MX9704978A (es) | 1997-10-31 |
AU4435096A (en) | 1996-07-31 |
WO1996021653A1 (de) | 1996-07-18 |
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