CN101600702B - 螺环特窗酸衍生物 - Google Patents
螺环特窗酸衍生物 Download PDFInfo
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- CN101600702B CN101600702B CN2008800018934A CN200880001893A CN101600702B CN 101600702 B CN101600702 B CN 101600702B CN 2008800018934 A CN2008800018934 A CN 2008800018934A CN 200880001893 A CN200880001893 A CN 200880001893A CN 101600702 B CN101600702 B CN 101600702B
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- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Abstract
本发明涉及新的式(I)螺环特窗酸衍生物,其中R1、R2、R3具有说明书中描述的含义。本发明还涉及制备所述衍生物的几种方法及所述衍生物作为农药的用途。
Description
本发明涉及新的螺环特窗酸衍生物,涉及其多种制备方法以及它们作为农药的用途。
已知某些取代的Δ3-二氢呋喃-2-酮衍生物具有除草特性(参见DE-A-4014420)。特窗酸衍生物作为原料的合成(例如,3-(2-甲基苯基)-4-羟基-5-(4-氟苯基)-Δ3-二氢呋喃酮-(2))同样描述于DE-A-4014420中。据称不具有任何杀昆虫和/或杀螨虫活性的类似结构的化合物由出版物Campbell et al.,J.Chem.Soc.,Perkin Trans.1,1985,(8)1567-76已知。另外还由以下文献已知具有除草、杀螨虫和杀昆虫特性的3-芳基-Δ3-二氢呋喃酮衍生物:EP-A-528156、EP-A-0647637、WO 95/26345、WO96/20196、WO 96/25395、WO 96/35664、WO 97/01535、WO 97/02243、WO 97/36868、WO 98/05638、WO 98/25928、WO 99/16748、WO99/43649、WO 99/48869、WO 99/55673、WO 00/42850、WO 01/17972、WO 01/23354、WO 01/74770、WO 03/013249、WO 04/024688、WO04/080962、WO 04/111042、WO 05/092897、WO 06/000355、WO06/029799、WO 06/089633、WO 07/048545和WO 07/073856。
然而,特别是在低施用率和低浓度下,这些化合物的杀螨虫和/或杀昆虫活性和/或杀螨虫和/或杀昆虫活性谱并不总是令人满意的。此外,这些化合物与一些作物植物的相容性并不总是足够。另外,这些化合物的毒理学特性和/或环境特性不总是完全令人满意。
本发明现提供新的式(I)化合物,
其中
R1、R2、R3彼此独立地代表烷基、卤素、卤代烷基、烷氧基、氰基或CO2-烷基,其中如果R1和R2代表甲基,则R3代表乙基、丙基或甲氧基,或者
R1和R2与它们所连接的碳原子一起代表一个未取代的或取代的可任选被1或2个杂原子间隔的环,并且
R3代表任选被卤素取代的C1-C4-烷基
或者
R1、R2和R3与它们所连接的碳原子一起代表任选取代的金刚烷基。
R1、R2和R3具有如上所述含义的式(I)化合物通过将式(II)化合物
各自与如下物质反应获得:
Aα)式(III)化合物
其中
R1、R2和R3具有上述含义,并且
Hal代表卤素(尤其是氯或溴)
或者
Aβ)式(IV)羧酸酐
其中
R1、R2和R3具有上述含义,
如果合适在一种稀释剂的存在下并且如果合适在一种酸结合剂的存在下进行;
或者
Aγ)式(V)活化的羧酸衍生物
其中
R1、R2和R3具有上述含义,
并且
U代表一个由羧酸活化试剂引入的离去基团,所述羧酸活化试剂例如羰基二咪唑、羰基二酰亚胺(如二环己基碳二亚胺)、磷酸化试剂(如POCI3、BOP-Cl)、卤化试剂,如亚硫酰氯、草酰氯、光气或氯甲酸酯,
如果合适合适在一种稀释剂的存在下并且如果合适在一种酸结合剂的存在下进行。
式(I)提供了本发明化合物的一般性定义。上述结构式中优选的取代基或基团范围如下:
R1、R2和R3优选各自独立地代表C1-C4-烷基、卤素、C1-C4-卤代烷基、C1-C4-烷氧基、氰基或CO2-C1-C4-烷基,
其中如果R1和R2代表甲基,则R3代表乙基、丙基或甲氧基,
或者
R1和R2与它们所连接的碳原子一起优选代表一个可任选被1或2个硫和/或氧原子间隔并且为未取代的或任选被甲基或乙基单取代或双取代的5-或6-元环,并且
R3优选代表任选由氟或氯单取代至五取代的C1-C4-烷基,
或者
R1、R2和R3与它们所连接的碳原子一起优选地代表金刚烷基。
在作为优选提及的基团中,卤素代表氟、氯和溴。
R1、R2、R3特别优选各自独立地代表甲基、乙基、丙基、氟、氯、溴、氯甲基、氟甲基、三氟甲基、甲氧基、乙氧基、丙氧基、氰基、CO2-CH3或CO2C2H5,其中如果R1和R2代表甲基,则R3代表乙基、丙基或甲氧基,
或者
R1和R2与它们所连接的碳原子一起特别优选地代表任选被1或2个氧原子间隔并且为未取代的或任选被甲基单取代或二取代的5-或6-元环,并且
R3特别优选代表甲基、乙基或三氟甲基,
或者
R1、R2和R3与它们所连接的碳原子一起特别优选地代表金刚烷基。
R1、R2、R3极特别优选各自独立地代表甲基、乙基、丙基、三氟甲基、甲氧基或乙氧基,其中如果R1和R2代表甲基,则R3代表乙基、丙基或甲氧基,
或者
R1和R2与它们所连接的碳原子一起极特别优选地代表一个可任选被1或2个氧原子间隔的未取代的5-或6-元环,并且
R3极特别优选代表甲基或三氟甲基,
或者
R1、R2和R3与它们所连接的碳原子一起极特别优选地代表金刚烷基。
本发明的方法(A)中作为原料所需的化合物(II)可由EP-A-528156的实施例I-a-33已知。
本发明的方法(A)中作为原料所需的一些碳酰氯(III)、羧酸酐(IV)和羧酸衍生物(V)可商购获得,或者可由通常已知的方法制备(见制备实施例)。
方法(A-α)的特征在于使式(II)化合物各自与式(III)的碳酰卤反应,如果合适在稀释剂的存在下并且如果合适在酸结合剂的存在下进行。
适用于本发明的方法(A-α)的稀释剂为所有对酰卤惰性的溶剂。优选使用烃,例如汽油、苯、甲苯、二甲苯和四氢化萘;还有卤代烃,如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯,还有酮,如丙酮和甲基异丙基酮,还有醚,如二乙醚、四氢呋喃和二噁烷,此外还有羧酸酯,如乙酸乙酯,以及强极性溶剂,如二甲亚砜和环丁砜。如果酰卤对于水解足够稳定,那么反应也可在水的存在下进行。
适用于本发明方法(A-α)的酸结合剂为所有常规酸受体。优选使用叔胺,例如三乙胺、吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环十一烯(DBU)、二氮杂双环壬烯(DBN)、Hünig碱和N,N-二甲基苯胺;以及碱土金属氧化物,例如氧化镁和氧化钙;还有碱金属和碱土金属的碳酸盐,例如碳酸钠、碳酸钾和碳酸钙;以及碱金属氢氧化物,例如氢氧化钠和氢氧化钾。
本发明方法(A-α)中的反应温度可在相对宽的范围内变化。一般而言,该方法在-20℃至+150℃、优选0℃至100℃的温度下实施。
实施本发明方法(A-α)时,式(II)的原料和式(III)的碳酰卤通常各自以大致相当的量使用。但是也可使用相对较大程度过量(最高达5mol)的碳酰卤。后处理通过常规方法进行。
方法(A-β)的特征在于使式(II)化合物与式(IV)羧酸酐反应,如果合适在稀释剂的存在下并且如果合适在酸结合剂的存在下进行。
用于本发明的方法(A-β)的合适的稀释剂优选为使用酰卤时也为优选的稀释剂。除此之外,过量的羧酸酐也可同时作为稀释剂。
对于方法(A-β),适当时加入的合适的酸结合剂优选为使用酰卤时也为优选的酸结合剂。
本发明方法(A-β)中的反应温度可在相对宽的范围内变化。一般而言,该方法在-20℃至+150℃、优选0℃至100℃的温度下实施。
实施本发明的方法(A-β)时,式(II)的原料和式(IV)的羧酸酐通常各自以大致相当的量使用。但是也可使用相对较大程度过量(最高达5mol)的羧酸酐。后处理通过常规方法进行。
一般而言,稀释剂和过量的羧酸酐以及形成的羧酸通过蒸馏或用有机溶剂或水洗涤除去。
方法(A-γ)的特征在于使式(II)化合物各自与式(V)的活化羧酸衍生物反应,如果合适在稀释剂的存在下并且如果合适在酸结合剂的存在下进行。
用于本发明的方法(A-γ)的反应的合适的酸结合剂为所有常规酸受体。优选使用叔胺,例如三乙胺、吡啶、DABCO、DBU、DBA、Hünig碱和N,N-二甲基苯胺;以及碱土金属氧化物,例如氧化镁和氧化钙;还有碱金属和碱土金属的碳酸盐,例如碳酸钠、碳酸钾和碳酸钙;以及碱金属氢氧化物,例如氢氧化钠和氢氧化钾。
用于本发明的方法(A-γ)的合适的稀释剂为所有对氯甲酸酯或氯甲酸硫酯呈惰性的溶剂。优选使用烃,例如汽油、苯、甲苯、二甲苯和四氢化萘;还有卤代烃,如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯甲苯;还有酮,如丙酮和甲基异丙基酮;还有醚,如二乙醚、四氢呋喃和二噁烷;此外还有羧酸酯,如乙酸乙酯;以及强极性溶剂,如二甲亚砜和环丁砜。
当实施本发明的方法(A-γ)时,反应温度可在相对宽的范围内变化。如果该方法在稀释剂和酸结合剂的存在下进行,则反应温度通常在-20℃至+100℃、优选0℃至50℃之间。
本发明的方法(A-γ)通常在常压下进行。
当实施本发明的方法(A-γ)时,式(II)的原料和合适的式(V)的活化羧酸衍生物通常各自以大致相当的量使用。但时也可使用相对较大程度过量(最高达2mol)的一种组分或另一种组分。后处理通过常规方法进行。一般而言,沉淀的盐被除去,剩余的反应混合物通过减压下除去稀释剂而浓缩。
本发明的活性化合物由于兼具良好的植物耐受性和对温血动物有利的毒性以及良好的环境耐受性,适用于保护植物和植物器官、提高采收产率、改进采收物的品质以及防治动物有害物,特别是农业、园艺、家畜饲养、森林、公园和休闲设施、贮存产品和材料保护以及卫生领域中遇到的昆虫、蛛形纲动物、蠕虫、线虫和软体动物。其可优选用作植物保护剂。它们对通常敏感和抗性物种以及全部或某些发育阶段具有活性。上述有害物包括:
虱目(Anoplura)(Phthiraptera),例如畜虱属(Damalinia spp.)、血虱属(Haematopinus spp.)、毛虱属(Linognathus spp.)、虱属(Pediculus spp.)、嚼虱属(Trichodectes spp.)。
蛛形纲(Arachnida),例如,粗脚粉螨(Acarus siro)、柑橘瘤瘿螨(Aceria sheldoni)、刺皮瘿螨属(Aculops spp.)、针刺瘿螨属(Aculus spp.)、花蜱属(Amblyomma spp.)、锐缘蜱属(Argas spp.)、牛蜱属(Boophilus spp.)、短须螨属(Brevipalpus spp.)、苜蓿苔螨(Bryobia praetiosa)、皮螨属(Chorioptes spp.)、鸡皮刺螨(Dermanyssus gallinae)、始叶螨属(Eotetranychus spp.)、梨上瘿螨(Epitrimerus pyri)、真叶螨属(Eutetranychus spp.)、瘿螨属(Eriophyes spp.)、半跗线螨属(Hemitarsonemus spp.)、璃眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、黑寡妇蜘蛛(Latrodectusmactans)、Metatetranychus spp.、小爪螨属(Oligonychus spp.)、钝缘蜱属(Ornithodoros spp.)、全爪螨属(Panonychus spp.)、桔芸锈螨(Phyllocoptruta oleivora)、侧多食跗线螨(Polyphagotarsonemus latus)、痒螨属(Psoroptes spp.)、扇头蜱属(Rhipicephalus spp.)、根螨属(Rhizoglyphus spp.)、疥螨属(Sarcoptes spp.)、中东金蝎(Scorpio maurus)、Stenotarsonemus spp.、跗线螨属(Tarsonemus spp.)、叶螨属(Tetranychus spp.)、Vasateslycopersici。
双壳软体动物(Bivalva)纲,例如,Dreissena spp.。
唇足目(Chilopoda),例如,地蜈蚣属(Geophilus spp.)、Scutigeraspp.。
鞘翅目(Coleoptera),例如,菜豆象(Acanthoscelides obtectus)、喙丽金龟属(Adoretus spp.)、杨树萤叶甲(Agelastica alni)、叩甲属(Agriotes spp.)、马铃薯鳃角金龟(Amphimallon solstitialis)、家具窃蠹(Anobium punctatum)、星天牛属(Anoplophora spp.)、花象属(Anthonomus spp.)、圆皮蠹属(Anthrenus spp.)、阿鳃金龟属(Apogonia spp.)、Atomaria spp.、毛皮蠹属(Attagenus spp.)、恶条豆象(Bruchidius obtectus)、豆象属(Bruchus spp.)、龟象属(Ceuthorhynchus spp.)、Cleonus mendicus、宽胸叩头虫属(Conoderus spp.)、根颈象属(Cosmopolites spp.)、褐新西兰肋翅鳃角金龟(Costelytra zealandica)、象虫属(Curculio spp.)、杨干隐喙象(Cryptorhynchus lapathi)、皮蠹属(Dermestes spp.)、叶甲属(Diabrotica spp.)、食植瓢虫属(Epilachna spp.)、Faustinus cubae、裸蛛甲(Gibbium psylloides)、黑异爪蔗金龟(Heteronychus arator)、Hylamorpha elegans、北美家天牛(Hylotrupes bajulus)、紫苜蓿叶象(Hypera postica)、Hypothenemus spp.、甘蔗大褐齿爪鳃金龟(Lachnosterna consanguinea)、马铃薯甲虫(Leptinotarsadecemlineata)、稻根象(Lissorhoptrus oryzophilus)、筒喙象属(Lixusspp.)、粉蠹属(Lyctus spp.)、油菜花露尾甲(Meligethes aeneus)、西方五月鳃角金龟(Melolontha melolontha)、Migdolus spp.、墨天牛属(Monochamus spp.)、Naupactus xanthographus、黄蛛甲(Niptushololeucus)、椰蛀犀金龟(Oryctes rhinoceros)、锯谷盗(Oryzaephilussurinamensis)、黑葡萄耳象(Otiorrhynchus sulcatus)、小青花金龟(Oxycetonia jucunda)、辣根猿叶虫(Phaedon cochleariae)、食叶鳃金龟属(Phyllophaga spp.)、日本弧丽金龟(Popillia japonica)、Premnotrypes spp.、油菜金头跳甲(Psylliodes chrysocephala)、蛛甲属(Ptinus spp.)、暗色瓢虫(Rhizobius ventralis)、谷蠹(Rhizoperthadominica)、谷象属(Sitophilus spp.)、尖隐喙象属(Sphenophorusspp.)、茎干象属(Sternechus spp.)、Symphyletes spp.、黄粉虫(Tenebriomolitor)、拟谷盗属(Tribolium spp.)、斑皮蠹属(Trogoderma spp.)、籽象属(Tychius spp.)、脊虎天牛属(Xylotrechus spp.)、距步甲属(Zabrus spp.)。
弹尾目(Collembola),例如,武装棘跳虫(Onychiurus armatus)。
革翅目(Dermaptera),例如,欧洲球螋(Forficula auricularia)。
倍足目(Diplopoda),例如,Blaniulus guttulatus。
双翅目(Diptera),例如,伊蚊属(Aedes spp.)、按蚊属(Anophelesspp.)、花园毛蚊(Bibio hortulanus)、红头丽蝇(Calliphoraerythrocephala)、地中海蜡实蝇(Ceratitis capitata)、金蝇属(Chrysomyia spp.)、锥蝇属(Cochliomyia spp.)、Cordylobiaanthropophaga、库蚊属(Culex spp.)、黄蝇属(Cuterebra spp.)、橄榄大实蝇(Dacus oleae)、人肤蝇(Dermatobia hominis)、果蝇属(Drosophila spp.)、厕蝇属(Fannia spp.)、胃蝇属(Gastrophilus spp.)、黑蝇属(Hylemyia spp.)、Hyppobosca spp.、皮蝇属(Hypoderma spp.)、斑潜蝇属(Liriomyza spp.)、绿蝇属(Lucilia spp.)、家蝇属(Muscaspp.)、绿蝽属(Nezara spp.)、狂蝇属(Oestrus spp.)、瑞典麦秆蝇(Oscinella frit)、藜泉蝇(Pegomyia hyoscyami)、草种蝇属(Phorbiaspp.)、螫蝇属(Stomoxys spp.)、虻属(Tabanus spp.)、Tannia spp.、欧洲大蚊(Tipula paludosa)、污蝇属(Wohlfahrtia spp.)。
腹足纲(Gastropoda),例如,Arion spp.、双脐螺属(Biomphalariaspp.)、小泡螺属(Bulinus spp.)、Deroceras spp.、土蜗属(Galba spp.)、椎实螺属(Lymnaea spp.)、钉螺属(Oncomelania spp.)、琥珀螺属(Succinea spp.)。
蠕虫纲(Helminths),例如,十二指肠钩口线虫(Ancylostomaduodenale)、斯里兰卡钩口线虫(Ancylostoma ceylanicum)、巴西钩口线虫(Acylostoma braziliensis)、钩口线虫属(Ancylostoma spp.)、似引蛔线虫(Ascaris lubricoides)、蛔虫属(Ascaris spp.)、马来布鲁线虫(Brugia malayi)、帝汶布鲁线虫(Brugia timori)、仰口线虫属(Bunostomum spp.)、夏柏特线虫属(Chabertia spp.)、枝睾吸虫属(Clonorchis spp.)、古柏线虫属(Cooperia spp.)、双腔吸虫属(Dicrocoelium spp.)、丝状网尾线虫(Dictyocaulus filaria)、阔节裂头绦虫(Diphyllobothrium latum)、麦地那龙线虫(Dracunculusmedinensis)、细粒棘球绦虫(Echinococcus granulosus)、多房棘球绦虫(Echinococcus multilocularis)、蠕形住肠蛲虫(Enterobiusvermicularis)、Faciola spp.、血毛线虫属(Haemonchus spp.)、异刺线虫属(Heterakis spp.)、矮小啮壳绦虫(Hymenolepis nana)、猪圆线虫属(Hyostrongulus spp.)、罗阿罗阿线虫(Loa Loa)、细颈线虫属(Nematodirus spp.)、结节线虫属(Oesophagostomum spp.)、后睾吸虫属(Opisthorchis spp.)、旋盘尾丝虫(Onchocerca volvulus)、奥斯脱线虫属(Ostertagia spp.)、并殖吸虫属(Paragonimus spp.)、Schistosomen spp.、富氏类圆线虫(Strongyloides fuelleborni)、粪类圆线虫(Strongyloides stercoralis)、粪圆线虫属(Stronyloides spp.)、牛带绦虫(Taenia saginata)、猪带绦虫(Taenia solium)、旋毛形线虫(Trichinella spiralis)、本地毛形线虫(Trichinella nativa)、株布氏旋毛虫(Trichinella britovi)、南方旋毛虫(Trichinella nelsoni)、Trichinella pseudopsiralis、毛圆线虫属(Trichostrongulus spp.)、Trichuris trichuria、班氏吴策线虫(Wuchereria bancrofti)。
此外,也可防治原生动物,例如艾美虫(Eimeria)。
异翅目(Heteroptera),例如,南瓜缘蝽(Anasa tristis)、拟丽蝽属(Antestiopsis spp.)、土长蝽属(Blissus spp.)、俊盲蝽属(Calocorisspp.)、Campylomma livida、异背长蝽属(Cavelerius spp.)、臭虫属(Cimex spp.)、Creontiades dilutus、胡椒缘蝽(Dasynus piperis)、Dichelops furcatus、厚氏长棒网蝽(Diconocoris hewetti)、棉红蝽属(Dysdercus spp.)、美洲蝽属(Euschistus spp.)、扁盾蝽属(Eurygasterspp.)、Heliopeltis spp.、Horcias nobilellus、稻缘蝽属(Leptocorisaspp.)、叶喙缘蝽(Leptoglossus phyllopus)、草盲蝽属(Lygus spp.)、蔗黑长蝽(Macropes excavatus)、盲蝽科(Miridae)、绿蝽属、Oebalusspp.、Pentomidae、方背皮蝽(Piesma quadrata)、壁蝽属(Piezodorusspp.)、棉伪斑腿盲蝽(Psallus seriatus)、Pseudacysta persea、红猎蝽属(Rhodnius spp.)、可可褐盲蝽(Sahlbergella singularis)、黑蝽属(Scotinophora spp.)、梨冠网蝽(Stephanitis nashi)、Tibraca spp.、锥猎蝽属(Triatoma spp.)。
同翅目(Homoptera),例如,无网长管蚜属(Acyrthosipon spp.)、Aeneolamia spp.、隆脉木虱属(Agonoscena spp.)、Aleurodes spp.、蔗粉虱属(Aleurolobus barodensis)、Aleurothrixus spp.、杧果叶蝉属(Amrasca spp.)、Anuraphis cardui、肾圆盾蚧属(Aonidiella spp.)、苏联黄粉蚜(Aphanostigma piri)、蚜属(Aphis spp)、葡萄叶蝉(Arboridia apicalis)、小圆盾蚧属(Aspidiella spp.)、圆盾蚧属(Aspidiotus spp.)、Atanus spp.、茄沟无网蚜(Aulacorthum solani)、Bemisia spp.、李短尾蚜(Brachycaudus helichrysii)、Brachycolus spp.、甘蓝蚜(Brevicoryne brassicae)、小褐稻虱(Calligypona marginata)、Carneocephala fulgida、甘蔗粉角蚜(Ceratovacuna lanigera)、沫蝉科(Cercopidae)、蜡蚧属(Ceroplastes spp.)、草莓钉蚜(Chaetosiphonfragaefolii)、蔗黄雪盾蚧(Chionaspis tegalensis)、茶绿叶蝉(Chloritaonukii)、核桃黑斑蚜(Chromaphis juglandicola)、黑褐圆盾蚧(Chrysomphalus ficus)、玉米叶蝉(Cicadulina mbila)、Coccomytilushalli、软蚧属(Coccus spp.)、茶藨隐瘤蚜(Cryptomyzus ribis)、Dalbulusspp.、Dialeurodes spp.、Diaphorina spp.、白背盾蚧属(Diaspis spp.)、Doralis spp.、履绵蚧属(Drosicha spp.)、西圆尾蚜属(Dysaphis spp.)、灰粉蚧属(Dysmicoccus spp.)、小绿叶蝉属(Empoasca spp.)、绵蚜属(Eriosoma spp.)、Erythroneura spp.、Euscelis bilobatus、咖啡地粉蚧(Geococcus coffeae)、假桃病毒叶蝉(Homalodisca coagulata)、梅大尾蚜(Hyalopterus arundinis)、吹绵蚧属(Icerya spp.)、片角叶蝉属(Idiocerus spp.)、扁喙叶蝉属(Idioscopus spp.)、灰飞虱(Laodelphax striatellus)、Lecanium spp.、蛎盾蚧属(Lepidosaphesspp.)、萝卜蚜(Lipaphis erysimi)、长管蚜属(Macrosiphum spp.)、Mahanarva fimbriolata、高粱蚜(Melanaphis sacchari)、Metcalfiellaspp.、麦无网蚜(Metopolophium dirhodum)、黑缘平翅斑蚜(Monelliacostalis)、Monelliopsis pecanis、瘤蚜属(Myzus spp.)、莴苣衲长管蚜(Nasonovia ribisnigri)、黑尾叶蝉属(Nephotettix spp.)、褐飞虱(Nilaparvata lugens)、Oncometopia spp.、Orthezia praelonga、杨梅缘粉虱(Parabemisia myricae)、Paratrioza spp.、片盾蚧属(Parlatoriaspp.)、瘿绵蚜属(Pemphigus spp.)、玉米蜡蝉(Peregrinus maidis)、绵粉蚧属(Phenacoccus spp.)、杨平翅绵蚜(Phloeomyzus passerinii)、忽布疣蚜(Phorodon humuli)、Phylloxera spp.、苏铁褐点并盾蚧(Pinnaspis aspidistrae)、臀纹粉蚧属(Planococcus spp.)、梨形原绵蚧(Protopulvinaria pyriformis)、桑白盾蚧(Pseudaulacaspispentagona)、粉蚧属(Pseudococcus spp.)、木虱属(Psylla spp.)、金小蜂属(Pteromalus spp.)、Pyrilla spp.、笠圆盾蚧属(Quadraspidiotusspp.)、Quesada gigas、平刺粉蚧属(Rastrococcus spp.)、缢管蚜属(Rhopalosiphum spp.)、黑盔蚧属(Saissetia spp.)、Scaphoides titanus、麦二叉蚜(Schizaphis graminum)、苏铁刺圆盾蚧(Selenaspidusarticulatus)、长唇基飞虱属(Sogata spp.)、白背飞虱(Sogatellafurcifera)、Sogatodes spp.、Stictocephala festina、Tenalapharamalayensis、Tinocallis caryaefoliae、广胸沫蝉属(Tomaspis spp.)、声蚜属(Toxoptera spp.)、温室粉虱(Trialeurodes vaporariorum)、个木虱属(Trioza spp.)、小叶蝉属(Typhlocyba spp.)、尖盾蚧属(Unaspisspp.)、Viteus vitifolii。
膜翅目(Hymenoptera),例如,松叶蜂属(Diprion spp.)、实叶蜂属(Hoplocampa spp.)、毛蚁属(Lasius spp.)、小家蚁(Monomoriumpharaonis)、胡蜂属(Vespa spp.)。
等足目(Isopoda),例如,鼠妇(Armadillidium vulgare)、栉水虱(Oniscus asellus)、球鼠妇(Porcellio scaber)。
等翅目(Isoptera),例如,散白蚁属(Reticulitermes spp.)、土白蚁属(Odontotermes spp.)。
鳞翅目(Lepidoptera),例如,桑剑纹夜蛾(Acronicta major)、烦夜蛾(Aedia leucomelas)、地老虎属(Agrotis spp.)、棉叶波纹夜蛾(Alabama argillacea)、干煞夜蛾属(Anticarsia spp.)、Barathrabrassicae、棉潜蛾(Bucculatrix thurberiella)、松尺蠖(Bupaluspiniarius)、亚麻黄卷蛾(Cacoecia podana)、Capua reticulana、苹果小卷蛾(Carpocapsa pomonella)、冬尺蛾(Cheimatobia brumata)、禾草螟属(Chilo spp.)、枞色卷蛾(Choristoneura fumiferana)、葡萄果蠹蛾(Clysia ambiguella)、Cnaphalocerus spp.、埃及金刚钻(Eariasinsulana)、地中海粉斑螟(Ephestia kuehniella)、黄毒蛾(Euproctischrysorrhoea)、切根虫属(Euxoa spp.)、脏切夜蛾属(Feltia spp.)、大蜡螟(Galleria mellonella)、Helicoverpa spp.、实夜蛾属(Heliothisspp.)、褐织蛾(Hofmannophila pseudospretella)、茶长卷蛾(Homonamagnanima)、苹果巢蛾(Hyponomeuta padella)、贪夜蛾属(Laphygmaspp.)、苹细蛾(Lithocolletis blancardella)、绿果冬夜蛾(Lithophaneantennata)、豆白隆切根虫(Loxagrotis albicosta)、毒蛾属(Lymantriaspp.)、黄褐天幕毛虫(Malacosoma neustria)、甘蓝夜蛾(Mamestrabrassicae)、稻毛胫夜蛾(Mocis repanda)、粘虫(Mythimna separata)、Oria spp.、水稻负泥虫(Oulema oryzae)、小眼夜蛾(Panolis flammea)、红铃麦蛾(Pectinophora gossypiella)、桔潜蛾(Phyllocnistis citrella)、菜粉蝶属(Pieris spp.)、菜蛾(Plutella xylostella)、斜纹夜蛾属(Prodenia spp.)、Pseudaletia spp.、大豆夜蛾(Pseudoplusiaincludens)、玉米螟(Pyrausta nubilalis)、灰翅夜蛾属(Spodopteraspp.)、Thermesia gemmatalis、袋谷蛾(Tinea pellionella)、幕谷蛾(Tineola bisselliella)、栎绿卷蛾(Tortrix viridana)、粉夜蛾属(Trichoplusia spp.)。
直翅目(Orthoptera),例如,家蟋(Acheta domesticus)、东方蜚蠊(Blatta orientalis)、德国蠊(Blattella germanica)、蝼蛄属(Gryllotalpa spp.)、马德拉蜚蠊(Leucophaea maderae)、飞蝗属(Locusta spp.)、黑蝗属(Melanoplus spp.)、美洲大蠊(Periplanetaamericana)、沙漠蝗(Schistocerca gregaria)。
蚤目(Siphonaptera),例如,角叶蚤属(Ceratophyllus spp.)、印鼠客蚤(Xenopsylla cheopis)。
综合目(Symphyla),例如,Scutigerella immaculata。
缨翅目(Thysanoptera),例如,稻蓟马(Baliothrips biformis)、Enneothrips flavens、花蓟马属(Frankliniella spp.)、网蓟马属(Heliothrips spp.)、温室条篱蓟马(Hercinothrips femoralis)、卡蓟马属(Kakothrips spp.)、葡萄蓟马(Rhipiphorothrips cruentatus)、硬蓟马属(Scirtothrips spp.)、Taeniothrips cardamoni、蓟马属(Thripsspp.)。
缨尾目(Thysanura),例如,衣鱼(Lepisma saccharina)。
植物寄生线虫包括,例如,鳗线虫属(Anguina spp.)、滑刃线虫属(Aphelenchoides spp.)、刺线虫属(Belonoaimus spp.)、伞滑刃线虫属(Bursaphelenchus spp.)、起绒草茎线虫(Ditylenchus dipsaci)、球异皮线虫属(Globodera spp.)、螺旋线虫属(Heliocotylenchus spp.)、异皮线虫属(Heterodera spp.)、长针线虫属(Longidorus spp.)、根结线虫属(Meloidogyne spp.)、短体线虫属(Pratylenchus spp.)、相似穿孔线虫(Radopholus similis)、小盘旋线虫属(Rotylenchusspp.)、毛刺线虫属(Trichodorus spp.)、矮化线虫属(Tylenchorhynchusspp.)、小垫刃线虫属(Tylenchulus spp.)、半穿刺线虫(Tylenchulussemipenetrans)、剑线虫属(Xiphinema spp.)。
如果合适,本发明的化合物也可以某些浓度或施用率用作除草剂、安全剂、生长调节剂,或者用作改善植物特性的药剂,或者用作杀微生物剂,例如杀真菌剂、抗霉剂、杀细菌剂、杀病毒剂(包括抵抗无壳病毒的药剂)或用作抵抗MLO(类支原体)和RLO(类立克次氏体)的药剂。如果合适,它们也可用作合成其它活性化合物的中间体或前体。
所有的植物及植物部位均可依据本发明予以处理。本发明中植物的含义应理解为所有的植物及植物种群,例如需要的及不需要的野生植物或作物植物(包括天然存在的作物植物)。作物植物可为可通过常规植物培育和优选法或通过生物技术和遗传工程方法或通过前述方法的结合而获得的植物,包括转基因植物,也包括受植物种苗权保护或不受其保护的植物栽培种。植物部位的含义应理解为植物所有的地上及地下部位及器官,例如枝条、叶、花和根,可提及的实例为叶、针叶、茎、干、花、子实体、果实、种子、根、块茎和根茎。植物部位还包括采收物以及无性与有性繁殖物,例如插枝、块茎、根茎、分枝和种子。
根据本发明的使用活性化合物对植物和植物部位进行的处理,通过常规处理方法直接进行或者通过使化合物作用于其所处环境、生境或储存空间来实现,所述常规处理方法例如浸液、喷雾、蒸发、弥雾、撒播、涂抹、注射,并且,对于繁殖材料,尤其是种子,还可包衣一层或多层。
本发明的活性化合物可转化为常规制剂,例如溶液剂、乳剂、可湿性粉剂、水基和油基悬浮剂、粉剂、粉末剂、膏剂、可溶性粉剂、可溶性颗粒剂、撒施颗粒剂、悬乳浓缩剂、经活性化合物浸渍的天然材料、经活性化合物浸渍的合成材料、肥料,以及聚合物中的微胶囊剂。
这些制剂以已知的方式制成,例如将活性化合物与稀释剂混合,即,与液体溶剂和/或固体载体混合,同时可任选使用表面活性剂,即乳化剂和/或分散剂和/或发泡剂。这些制剂可在适当的装置中制备,或者在施用之前或其间制备。
适于用作助剂的是适用于赋予组合物本身和/或由其得到的制剂(例如喷洒液、拌种剂)以特殊性能——如某些工艺性能和/或特定的生物学性能——的物质。典型的合适的助剂有:填充剂、溶剂和载体。
合适的填充剂有,例如水,极性和非极性有机化学液体,例如来自芳香烃和非芳香烃类(如石蜡、烷基苯、烷基萘、氯苯)、醇和多元醇类(如果合适,可以是被取代的、醚化的和/或酯化的)、酮类(如丙酮、环己酮)、酯类(包括脂肪和油)以及(聚)醚类、未取代的和取代的胺类、酰胺类、内酰胺类(如N-烷基吡咯烷酮)和内酯类,砜类和亚砜类(如二甲亚砜)。
如果使用水作为填充剂,还可使用例如有机溶剂作为助溶剂。合适的液体溶剂主要有:芳香族化合物,例如二甲苯、甲苯或烷基萘;氯代芳香族化合物和氯代脂族烃,例如氯苯、氯乙烯或二氯甲烷;脂族烃,例如环己烷或石蜡,例如石油馏分、矿物油和植物油;醇,例如丁醇或乙二醇,及它们的醚和酯;酮,例如丙酮、甲乙酮、甲基异丁基酮或环己酮;强极性溶剂如二甲亚砜;以及水。
适合的固体载体有:
例如,铵盐和磨碎的天然矿物例如高岭土、粘土、滑石、白垩、石英、凹凸棒石、蒙脱石或硅藻土,以及磨碎的合成矿物,例如高度分散的二氧化硅、氧化铝和硅酸盐;适用于颗粒剂的固体载体为:例如粉碎并分级的天然岩石例如方解石、大理石、浮石、海泡石和白云石,及合成的无机和有机粉末的颗粒以及有机物质例如纸、锯屑、椰壳、玉米穗轴和烟草茎的颗粒;适合的乳化剂和/或发泡剂为:例如非离子和阴离子乳化剂,例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、芳基磺酸盐及蛋白质水解产物;适合的分散剂为非离子性和/或离子性物质,例如属于以下类别的物质:醇-POE和/或-POP醚、酸和/或POP-POE酯、烷基芳基和/或POP-POE醚、脂肪-和/或POP-POE加成物、POE-和/或POP-多元醇衍生物、POE-和/或POP-山梨醇-或-糖加成物、烷基或芳基硫酸盐、烷基-或芳基磺酸盐,以及烷基或芳基磷酸盐或者相应的PO-醚加成物。此外,合适的低聚物或高聚物,例如由乙烯单体形成的、由丙烯酸形成的低聚物或高聚物,由EO和/或PO单独形成的或与如(多元)醇或(多元)胺组合形成的低聚物或高聚物。还可采用木质素及其磺酸衍生物,未改性的和改性的纤维素、芳香的和/或脂族磺酸及它们与甲醛的加成物。
制剂中可使用增粘剂,例如羧甲基纤维素;以及粉末、颗粒或胶乳形式的天然及合成聚合物,例如阿拉伯树胶、聚乙烯醇及聚乙酸乙烯酯;以及天然磷脂,例如脑磷脂和卵磷脂,以及合成磷脂。
可使用着色剂,例如无机颜料——如氧化铁、氧化钛和普鲁士蓝,有机染料——如茜素染料、偶氮染料和金属酞菁染料,以及微量营养物——如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
其它可能的添加剂有香料、矿物质或植物,任选改性的油、蜡和营养物(包括微量营养物)如铁、锰、硼、铜、钴、钼和锌的盐。
还可含有稳定剂,例如低温稳定剂、防腐剂、抗氧化剂、光稳定剂或者其它改进化学和/或物理稳定性的试剂。
制剂通常包括0.01至98重量%、优选0.5至90重量%的活性化合物。
本发明的活性化合物可以其市售制剂以及由所述制剂与其它活性化合物混合所制备的使用形式使用,所述其它活性化合物例如杀昆虫剂、引诱剂、消毒剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节物质、除草剂、安全剂、肥料或化学信息物质。
特别有利的混合组分有,例如以下化合物:
杀真菌剂:
核酸合成抑制剂
苯霜灵(benalaxyl)、高效苯霜灵(benalaxyl-M)、磺嘧菌灵(bupirimate)、chiralaxyl、clozylacon、甲菌定(dimethirimol)、乙菌定(ethirimol)、呋氨丙灵(furalaxyl)、恶霜灵(hymexazol)、甲霜灵(metalaxyl)、精甲霜灵(metalaxyl-M)、甲呋酰胺(ofurace)、噁霜灵(oxadixyl)、喹菌酮(oxolinic acid)
有丝分裂和细胞分裂抑制剂
苯菌灵(benomyl)、多菌灵(carbendazim)、乙霉威(diethofencarb)、麦穗宁(fuberidazole)、戊菌隆(pencycuron)、噻菌灵(thiabendazole)、甲基托布津(thiophanate-methyl)、苯酰菌胺(zoxamide)
呼吸链复合体I抑制剂
氟嘧菌胺(diflumetorim)
呼吸链复合体II抑制剂
啶酰菌胺(boscalid)、萎锈灵(carboxin)、甲呋酰胺(fenfuram)、氟酰胺(flutolanil)、呋吡唑灵(furametpyr)、灭锈胺(mepronil)、氧化萎锈灵(oxycarboxin)、吡噻菌胺(penthiopyrad)、噻氟唑菌(thifluzamide)
呼吸链复合体III抑制剂
嘧菌酯(azoxystrobin)、氰霜唑(cyazofamid)、醚菌胺(dimoxystrobin)、enestrobin、噁唑酮菌(famoxadone)、咪唑菌酮(fenamidone)、氟嘧菌酯(fluoxastrobin)、醚菌酯(kresoxim-methyl)、苯氧菌胺(metominostrobin)、肟醚菌胺(orysastrobin)、唑菌胺酯(pyraclostrobin)、啶氧菌酯(picoxystrobin)、肟菌酯(trifloxystrobin)
解偶联剂(decoupler)
敌螨普(dinocap)、氟啶胺(fluazinam)
ATP生成抑制剂
薯瘟锡(fentin acetate)、三苯锡氯(fentin chloride)、毒菌锡(fentinhydroxide)、硅噻菌胺(silthiofam)
氨基酸生物合成和蛋白质生物合成抑制剂
胺扑灭(andoprim)、灭瘟素(blasticidin-S)、嘧菌环胺(cyprodinil)、春雷霉素(kasugamycin)、春雷霉素水合盐酸盐(kasugamycinhydrochloride hydrate)、嘧菌胺(mepanipyrim)、嘧霉胺(pyrimethanil)
信号转导抑制剂
拌种咯(fenpiclonil)、咯菌腈(fludioxonil)、苯氧喹啉(quinoxyfen)
脂类和膜合成抑制剂
乙菌利(chlozolinate)、异菌脲(iprodione)、腐霉利(procymidone)、乙烯菌核利(vinclozolin)
氨丙膦酸(ampropylfos)、氨丙膦酸钾(potassium-ampropylfos)、敌瘟磷(edifenphos)、异稻瘟净(iprobenfos)(IBP)、稻瘟灵(isoprothiolane)、吡菌磷(pyrazophos)
甲基立枯磷(tolclofos-methyl)、联苯
iodocarb、霜霉威(propamocarb)、霜霉威盐酸盐(propamocarbhydrochloride)、
麦角甾醇生物合成抑制剂
环酰菌胺(fenhexamid)、
氧环唑(azaconazole)、联苯三唑醇(bitertanol)、糠菌唑(bromuconazole)、环丙唑醇(cyproconazole)、苄氯三唑醇(diclobutrazole)、苯醚甲环唑(difenoconazole)、烯唑醇(diniconazole)、R-烯唑醇(diniconazole-M)、氟环唑(epoxiconazole)、乙环唑(etaconazole)、腈苯唑(fenbuconazole)、氟喹唑(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、呋菌唑(furconazole)、呋醚唑(furconazole-cis)、己唑醇(hexaconazole)、亚胺唑(imibenconazole)、种菌唑(ipconazole)、叶菌唑(metconazole)、腈菌唑(myclobutanil)、多效唑(paclobutrazole)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙硫菌唑(prothioconazole)、硅氟唑(simeconazole)、戊唑醇(tebuconazole)、四氟醚唑(tetraconazole)、三唑酮(triadimefon)、唑菌醇(triadimenol)、灭菌唑(triticonazole)、烯效唑(uniconazole)、烯霜苄唑(voriconazole)、抑霉唑(imazalil)、烯菌灵(imazalil sulphate)、恶咪唑(oxpoconazole)、氯苯嘧啶醇(fenarimol)、呋嘧醇(flurprimidole)、氟苯嘧啶醇(nuarimol)、啶斑肟(pyrifenox)、嗪氨灵(triforine)、稻瘟酯(pefurazoate)、咪鲜胺(prochloraz)、氟菌唑(triflumizole)、烯霜苯唑(viniconazole),
4-十二烷基-2,6-二甲基吗啉(aldimorph)、十二环吗啉(dodemorph)、吗菌灵(dodemorph acetate)、丁苯吗啉(fenpropimorph)、十三吗啉(tridemorph)、苯锈啶(fenpropidin)、螺环菌胺(spiroxamine),
萘替芬(naftifine)、稗草丹(pyributicarb)、特比萘芬(terbinafine)
细胞壁合成抑制剂
苯噻菌胺(benthiavalicarb)、双丙氨膦(bialaphos)、烯酰吗啉(dimethomorph)、氟吗啉(flumorph)、异丙菌胺(iprovalicarb)、多抗霉素(polyoxins)、多氧霉素(polyoxorim)、有效霉素(validamycin A)
黑色素生物合成抑制剂
环丙酰菌胺(capropamid)、双氯氰菌胺(diclocymet)、氰菌胺(fenoxanil)、四氯苯酞(phthalid)、咯喹酮(pyroquilon)、三环唑(tricyclazole)
抗性诱导剂
苯并噻二唑(acibenzolar-S-methyl)、烯丙苯噻唑(probenazole)、噻酰菌胺(tiadinil)
具有多位点活性的化合物
敌菌丹(captafol)、克菌丹(captan)、百菌清(chlorothalonil)、铜盐,如:氢氧化铜、环烷酸铜、氧氯化铜、硫酸铜、氧化铜、喹啉铜(oxine-copper),以及波尔多液(Bordeaux mixture)、苯氟磺胺(dichlofluanid)、二氰蒽醌(dithianon)、多果定(dodine)、多果定游离碱(dodine free base)、福美铁(ferbam)、灭菌丹(folpet)、氟灭菌丹(fluorofolpet)、双胍盐(guazatine)、双胍辛乙酸盐(guazatine acetate)、双胍辛胺(iminoctadine)、双八胍盐(iminoctadine albesilate)、双胍辛胺乙酸盐(iminoctadine triacetate)、代森锰铜(mancopper)、代森锰锌(mancozeb)、代森锰(maneb)、代森联(metiram、metiram zinc)、丙森锌(propineb)、硫和包括多硫化钙的硫制剂、福美双(thiram)、甲苯氟磺胺(tolylfluanid)、代森锌(zineb)、福美锌(ziram)
作用机理未知的化合物
amibromdol、苯噻硫氰(benthiazol)、bethoxazin、卡巴西霉素(capsimycin)、香芹酮(carvone)、灭螨猛(chinomethionat)、氯化苦(chloropicrin)、硫杂灵(cufraneb)、环氟菌胺(cyflufenamid)、霜脲氰(cymoxanil)、棉隆(dazomet)、咪菌威(debacarb)、哒菌酮(diclomezine)、双氯酚(dichlorophen)、氯硝胺(dicloran)、野燕枯(difenzoquat)、苯敌快(difenzoquat methyl sulfate)、二苯胺(diphenylamine)、噻唑菌胺(ethaboxam)、嘧菌腙(ferimzone)、氟酰菌胺(flumetover)、磺菌胺(flusulfamide)、氟吡菌胺(fluopicolide)、氟氯菌核利(fluoroimide)、六氯苯(hexachlorobenzene)、8-羟基喹啉(8-hydroxyquinoline sulfate)、人间霉素(irumamycin)、磺菌威(methasulfocarb)、苯菌酮(metrafenone)、异硫氰酸甲酯、米多霉素(mildiomycin)、多马霉素(natamycin)、福美镍(nickel dimethyldithiocarbamate)、酞菌酯(nitrothal-isopropyl)、辛噻酮(octhilinone)、oxamocarb、oxyfenthiin、五氯酚(pentachlorophenol)及其盐、2-苯基苯酚及其盐,病花灵(piperalin)、propanosine-sodium、丙氧喹啉(proquinazid)、硝吡咯菌素(pyrrolnitrin)、五氯硝基苯(quintozene)、叶枯酞(tecloftalam)、四氯硝基苯(tecnazene)、咪唑嗪(triazoxide)、水杨菌胺(trichlamide)、氰菌胺(zarilamid),以及2,3,5,6-四氯-4-(甲磺酰基)吡啶、N-(4-氯-2-硝基苯基)-N-乙基-4-甲基苯磺酰胺、2-氨基-4-甲基-N-苯基-5-噻唑甲酰胺、2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)吡啶甲酰胺、3-[5-(4-氯苯基)-2,3-二甲基异噁唑烷-3-基]吡啶、顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)环庚醇、2,4-二氢-5-甲氧基-2-甲基-4-[[[[1-[3-(三氟甲基)苯基]亚乙基]氨基]氧基]甲基]苯基]-3H-1,2,3-三唑-3-酮(185336-79-2)、1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯、3,4,5-三氯-2,6-吡啶二腈、2-[[[环丙基-[(4-甲氧基苯基)亚氨基]甲基]硫代]甲基]-α-(甲氧基亚甲基)苯乙酸甲酯、4-氯-α-丙炔氧基-N-[2-[3-甲氧基-4-(2-丙炔氧基)苯基]乙基]苯乙酰胺、(2S)-N-[2-[4-[[3-(4-氯苯基)-2-丙炔基]氧基]-3-甲氧基苯基]乙基]-3-甲基-2-[(甲磺酰基)氨基]丁酰胺、5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)[1,2,4]三唑并[1,5-a]嘧啶、5-氯-6-(2,4,6-三氟苯基)-N-[(1R)-1,2,2-三甲基丙基][1,2,4]三唑并[1,5-a]嘧啶-7-胺、5-氯-N-[(1R)-1,2-二甲基丙基]-6-(2,4,6-三氟苯基)[1,2,4]三唑并[1,5-a]嘧啶-7-胺、N-[1-(5-溴-3-氯代吡啶-2-基)乙基]-2,4-二氯烟酰胺、N-(5-溴-3-氯代吡啶-2-基)甲基-2,4-二氯烟酰胺、2-丁氧基-6-碘代-3-丙基苯并吡喃-4-酮、N-{(Z)-[(环丙基甲氧基)亚氨基][6-(二氟甲氧基)-2,3-二氟苯基]甲基}-2-苯乙酰胺、N-(3-乙基-3,5,5-三甲基环己基)-3-甲酰氨基-2-羟基苯甲酰胺、2-[[[[1-[3-(1-氟-2-苯基乙基)氧基]苯基]亚乙基]氨基]氧基]甲基]-α-(甲氧基亚氨基)-N-甲基-αE-苯乙酰胺、N-{2-[3-氯-5-(三氟甲基)吡啶-2-基]乙基}-2-(三氟甲基)苯甲酰胺、N-(3′,4′-二氯-5-氟联苯基-2-基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、N-(6-甲氧基-3-吡啶基)环丙甲酰胺、1-[(4-甲氧基苯氧基)甲基]-2,2-二甲基丙基-1H-咪唑-1-羧酸、O-{1-[(4-甲氧基苯氧基)甲基]-2,2-二甲基丙基]-1H-咪唑-1-硫代羟酸、2-(2-{[6-(3-氯-2-甲基苯氧基)-5-氟嘧啶-4-基]氧基}苯基)-2-(甲氧亚氨基)-N-甲基乙酰胺
杀细菌剂:
溴硝醇(bronopol)、双氯酚、三氯甲基吡啶(nitrapyrin)、福美镍、春雷霉素、辛噻酮、羧酸呋喃(furancarboxylic acid)、土霉素(oxytetracycline)、烯丙苯噻唑、链霉素(streptomycin)、叶枯酞、硫酸铜和其它铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
乙酰胆碱酯酶(AChE)抑制剂
氨基甲酸酯类,
例如,棉铃威(alanycarb)、涕灭威(aldicarb)、涕灭砜威(aldoxycarb)、除害威(allyxycarb)、灭害威(aminocarb)、噁虫威(bendiocarb)、丙硫克百威(benfuracarb)、合杀威(bufencarb)、畜虫威(butacarb)、丁酮威(butocarboxim)、丁酮砜威(butoxycarboxim)、甲萘威(carbaryl)、克百威(carbofuran)、丁硫克百威(carbosulfan)、除线威(cloethocarb)、敌蝇威(dimetilan)、乙硫苯威(ethiofencarb)、丁苯威(fenobucarb)、苯硫威(fenothiocarb)、伐虫脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、威百亩(metam-sodium)、甲硫威(methiocarb)、灭多威(methomyl)、速灭威(metolcarb)、杀线威(oxamyl)、抗蚜威(pirimicarb)、猛杀威(promecarb)、残杀威(propoxur)、硫双威(thiodicarb)、久效威(thiofanox)、混杀威(trimethacarb)、灭除威(XMC)、灭杀威(xylylcarb)、唑蚜威(triazamate)
有机磷酸酯类,
例如,乙酰甲胺磷(acephate)、甲基吡恶磷(azamethiphos)、保棉磷(azinphos-methyl)、益棉磷(azinphos-ethyl)、乙基溴硫磷(bromophos-ethyl)、溴苯烯磷(bromfenvinfos(-methyl))、特嘧硫磷(butathiofos)、硫线磷(cadusafos)、三硫磷(carbophenothion)、氯氧磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲硫磷(chlormephos)、甲基毒死蜱(chlorpyrifos-methyl)、毒死蜱(chlorpyrifos-ethyl)、蝇毒磷(coumaphos)、苯腈磷(cyanofenphos)、杀螟腈(cyanophos)、毒虫畏、甲基内吸磷(demeton-S-methyl)、砜吸磷(demeton-S-methylsulfone)、氯亚胺硫磷(dialifos)、二嗪磷(diazinon)、除线磷(dichlofenthion)、敌敌畏/DDVP(dichlorvos/DDVP)、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、蔬果磷(dioxabenzofos)、乙拌磷(disulfoton)、EPN、乙硫磷(ethion)、灭线磷(ethoprophos)、乙嘧硫磷(etrimfos)、伐灭磷(famphur)、苯线磷(fenamiphos)、杀螟硫磷(fenitrothion)、丰索磷(fensulfothion)、倍硫磷(fenthion)、吡氟硫磷(flupyrazofos)、地虫硫磷(fonofos)、安硫磷(formothion)、丁苯硫磷(fosmethilan)、噻唑磷(fosthiazate)、庚烯磷(heptenophos)、碘硫磷(iodofenphos)、异稻瘟净、氯唑磷(isazofos)、异柳磷(isofenphos)、O-水杨酸异丙酯、恶唑磷(isoxathion)、马拉硫磷(malathion)、灭蚜磷(mecarbam)、虫螨畏(methacrifos)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧乐果(omethoate)、亚砜磷(oxydemeton-methyl)、甲基对硫磷(parathion-methyl)、对硫磷(parathion-ethyl)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀硫磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、乙丙磷威(phosphocarb)、辛硫磷(phoxim)、甲基嘧啶磷(pirimiphos-methyl)、嘧啶磷(pirimiphos-ethyl)、丙溴磷(profenofos)、丙虫磷(propaphos)、胺丙畏(propetamphos)、丙硫磷(prothiofos)、发硫磷(prothoate)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、哒硫磷(pyridathion)、喹硫磷(quinalphos)、硫线磷(sebufos)、治螟磷(sulfotep)、硫丙磷(sulprofos)、丁基嘧啶磷(tebupirimphos)、双硫磷(temephos)、特丁硫磷(terbufos)、杀虫畏(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(triclorfon)、蚜灭磷(vamidothion)
钠通道调节剂/电位依赖性钠通道阻断剂
拟除虫菊酯类,
例如,氟酯菊酯(acrinathrin)、烯丙菊酯(d-顺-反,d-反)(allethrin(d-cis-trans,d-trans))、β-氟氯氰菊酯(beta-cyfluthrin)、氟氯菊酯(bifenthrin)、生物烯丙菊酯(bioallethrin)、生物烯丙菊酯-S-环戊基异构体、bioethanomethrin、生物氯菊酯(biopermethrin)、右旋反灭虫菊酯(bioresmethrin)、二氯炔戊菊酯(chlovaporthrin)、顺式氯氰菊酯、顺式灭虫菊(cis-resmethrin)、顺式氯菊酯(cis-permethrin)、功夫菊酯(clocythrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、氯氟氰菊酯(cyhalothrin)、氯氰菊酯(α-、β-、θ-、ζ-)(cypermethrin(alpha-,beta-,theta-,zeta-))、苯醚氯菊酯(cyphenothrin)、溴氰菊酯(deltamethrin)、烯炔菊酯(1R异构体)(empenthrin(1R isomer))、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、五氟苯菊酯(fenfluthrin)、甲氰菊酯(fenpropathrin)、吡氯氰菊酯(fenpyrithrin)、灭杀菊酯(fenvalerate)、溴氟菊酯(flubrocythrinate)、氟氰戊菊酯(flucythrinate)、氟丙苄醚(flufenprox)、氟氯苯菊酯(flumethrin)、氟胺氰菊酯(fluvalinate)、氟丙苯醚(fubfenprox)、γ-氯氟氰菊酯(gamma-cyhalothrin)、炔咪菊酯(imiprothrin)、噻嗯菊酯(kadethrin)、λ-氯氟氰菊酯(lambda-cyhalothrin)、甲氧苄氟菊酯(metofluthrin)、氯菊酯(顺-、反-)、苯醚菊酯(1R-反式异构体)(phenothrin(1R trans-isomer)、炔酮菊酯(prallethrin)、丙氟菊酯(profluthrin)、protrifenbute、反灭虫菊(pyresmethrin)、灭虫菊、RU 15525、氟硅菊酯(silafluofen)、氟胺氰菊酯(tau-fluvalinate)、七氟菊酯(tefluthrin)、环戊烯丙菊酯(terallethrin)、胺菊酯(1R异构体)(tetramethrin(1R isomer))、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin)、ZXI 8901、除虫菊素(pyrethrin,pyrethrum))
DDT
噁二嗪类,
例如茚虫威(indoxacarb)
缩氨基脲类,
例如氰氟虫胺(metaflumizone,BAS 3201)
乙酰胆碱受体激动剂/拮抗剂
氯烟碱基类(chloronicotinyls),
例如,啶虫脒(acetamiprid)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、烯啶虫胺(nitenpyram)、硝虫噻嗪(nithiazine)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)
烟碱(nicotine)、杀虫磺(bensultap)、杀螟丹(cartap)
乙酰胆碱受体调节剂
spinosyn类,
例如多杀菌素(spinosad)
GABA受控氯离子通道拮抗剂
有机氯类,
例如,毒杀芬(camphechlor)、氯丹(chlordane)、硫丹(endosulfan)、林丹(gamma-HCH)、HCH、七氯(heptachlor)、林丹(lindane)、甲氧滴滴涕(methoxychlor)
苯基吡唑类(fiproles)
例如,乙酞虫腈(acetoprole)、乙虫腈(ethiprole)、氟虫腈(fipronil)、pyrafluprole、pyripole、氟吡唑虫(vaniliprole)
氯离子通道活化剂类
mectin类
例如,阿维菌素(avermectin)、埃玛菌素(emamectin)、甲氨基阿维菌素苯甲酸盐(emamectin-benzoate)、伊维菌素(ivermectin)、米尔倍霉素(milbemycin)
保幼激素模拟物类,
例如,苯虫醚(diofenolan)、保幼醚(epofenonane)、苯氧威(fenoxycarb)、烯虫乙酯(hydroprene)、烯虫炔酯(kinoprene)、烯虫酯(methoprene)、吡丙醚(pyriproxifen)、烯虫硫酯(triprene)
蜕皮激素激动剂/干扰剂类(disruptor)
二酰基肼类,
例如,环虫酰肼(chromafenozide)、氯虫酰肼(halofenozide)、甲氧虫酰肼(methoxyfenozide)、虫酰肼(tebufenozide)
几丁质生物合成抑制剂
苯甲酰脲类,
例如,双三氟虫脲(bistrifluron)、定虫隆(chlorfluazuron)、氟脲杀(diflubenzuron)、氟啶蜱脲(fluazuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氟丙氧脲(lufenuron)、双苯氟脲(novaluron)、多氟脲(noviflumuron)、氟幼脲(penfluron)、伏虫磷(teflubenzuron)、杀虫隆(triflumuron)
噻嗪酮(buprofezin)
灭蝇胺(cyromazine)
氧化磷酸化抑制剂,ATP干扰剂类
丁醚脲(diafenthiuron)
有机锡化合物类,
例如三唑锡(azocyclotin)、三环锡(cyhexatin)、苯丁锡(fenbutatin-oxide)
通过打断H-质子梯度而起作用的氧化磷酸化解偶联剂类
吡咯类,
例如虫螨腈(chlorfenapyr)
二硝基苯酚类,
例如乐杀螨(binapacryl)、消螨通(dinobuton)、敌螨普(dinocap)、DNOC、meptyldinocap
位点-I(site-I)电子转移抑制剂类
METI类,
例如喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、嘧螨醚(pyrimidifen)、哒螨灵(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)
灭蚁腙(hydramethylnon)
三氯杀螨醇(dicofol)
位点-II电子转移抑制剂类
鱼藤酮(rotenone)
位点-III电子转移抑制剂类
灭螨醌(acequinocyl)、嘧螨酯(fluacrypyrim)
昆虫肠道膜微生物干扰剂类
苏云金杆菌(Bacillus thuringiensis)菌株
脂肪合成抑制剂类
特窗酸类,
例如,螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)
特特拉姆酸类,
例如螺虫乙酯(spirotetramat)、顺-3-(2,5-二甲基苯基)-4-羟基-8-甲氧基-1-氮杂螺环[4.5]癸-3-烯-2-酮
甲酰胺类,
例如氟啶虫酰胺(flonicamid)
章鱼胺能激动剂类,
例如双甲脒(amitraz)
镁刺激ATP酶抑制剂类,
炔螨特(propargite)
沙蚕毒素类似物,
例如杀虫环草酸盐(thiocyclam hydrogen oxalate)、杀虫双(thiosultap-sodium)
兰诺定受体激动剂,
苯甲酸二甲酰胺类,
例如氟虫酰胺(flubendiamide)
邻氨基苯甲酰胺类(anthranilamide)类,例如
Rynaxapyr(3-溴-N-{4-氯-2-甲基-6-[(甲氨基)羰基]苯基}-1-(3-氯吡啶-2-基)-1H-吡唑-5-甲酰胺)
生物制剂类、激素类或信息素类
印楝素(azadirachtin)、芽孢杆菌类(Bacillus spec.)、白僵菌类(Beauveria spec.)、十二碳二烯醇(codlemone)、绿僵菌属(Metarrhizium spec.)、拟青霉属(Paecilomyces spec.)、敌贝特(thuringiensin)、轮枝菌属(Verticillium spec.)
作用机理未知或不明确的活性化合物类
熏蒸剂类,
例如磷化铝、甲基溴、硫酰氟
拒食剂类,
例如冰晶石(cryolite)、氟啶虫酰胺、吡蚜酮(pymetrozine)
螨虫生长抑制剂类,
例如四螨嗪(clofentezine)、乙螨唑(etoxazole)、噻螨酮(hexythiazox)
amidoflumet、benclothiaz、苯螨特(benzoximate)、联苯肼酯(bifenazate)、溴螨酯(bromopropylate)、噻嗪酮(buprofezin)、灭螨锰、杀虫脒(chlordimeform)、乙酯杀螨醇(chlorobenzilate)、氯化苦、clothiazoben、cycloprene、cyflumetofen、环虫腈(dicyclanil)、fenoxacrim、氟硝二苯胺(fentrifanil)、flubenzimine、flufenerim、氟螨嗪(flutenzin)、红铃虫性诱剂(gossyplure)、伏虫腙、japonilure、恶虫酮(metoxadiazone)、石油、增效醚(piperonyl butoxide)、油酸钾(potassium oleate)、啶虫丙醚(pyridalyl)、氟虫胺(sulfluramid)、三氯杀螨醇(tetradifon)、杀螨硫醚(tetrasul)、苯螨噻(triarathene)、增效炔醚(verbutin)。
还可与其它已知活性化合物例如除草剂、肥料、生长调节剂、安全剂、化学信息物质混合,也可与改善植物特性的药剂混合。
用作杀虫剂时,本发明的活性化合物也可以市售制剂以及由所述制剂与增效剂混合所制备的使用形式存在。增效剂为通过其加入可提高活性化合物活性、而其本身不一定具有活性的化合物。
用作杀虫剂时,本发明的活性化合物也可以市售制剂以及由所述制剂与抑制剂混合所制备的使用形式存在,所述抑制剂可在活性化合物用于植物的环境、植物部位表面或植物组织后减少其降解。
由市售制剂制备的使用形式的活性化合物含量可在较宽的范围内变化。使用形式的活性化合物浓度可为0.00000001至95重量%的活性化合物,优选0.00001至1重量%。
这些化合物以适合于使用形式的常规方式使用。
如上所述,可依据本发明处理所有的植物和其部位。在一个优选实施方案中,处理了野生的植物种和植物栽培种、或由常规生物育种方法例如杂交或原生质体融合获得的植物种和植物栽培种、以及所述植物种和植物栽培种的部位。在另一优选实施方案中,处理了由遗传工程方法、如果合适还可与常规方法相结合而获得的转基因植物和植物栽培种(遗传修饰的生物(genetic modified organism))及其部位。术语“部位”或“植物的部位”或“植物部位”解释如上。
特别优选依据本发明进行处理的植物为各自市售或使用的植物品种。植物品种的含义理解为由常规育种、诱变或重组DNA技术获得的具有新特性(“特征”)的植物。它们可以是栽培种、生物型(biotype)和基因型形式。
依据植物种或植物栽培种、其种植地点和生长条件(土壤、气候、植物生长期、营养(diet)),本发明的处理也可产生超加和性(superadditive)(“协同的”)效应。由此可取得如下超过实际预期的效果,例如可降低本发明使用的物质和组合物的施用率和/或拓宽其活性谱和/或提高其活性、改善植物生长状况、提高高温或低温耐受性、提高对干旱或者对水中或土壤中含盐量的耐受性、提高开花品质、使采收更简易、加速成熟、提高采收产量、提高采收产品的质量和/或改善其营养价值、改善采收产品的贮存稳定性和/或其加工性能。
优选的依据本发明处理的转基因植物或植物栽培种(通过遗传工程方法获得)包括通过遗传修饰而接受遗传物质的所有植物,所述遗传物质将特别有利的、有用的特征赋予所述植物。所述特征的实例有改善植物生长状况、提高高温或低温耐受性、提高对干旱或者对水中或土壤中含盐量的耐受性、提高开花品质、使采收更简易、加速成熟、提高采收产量、提高采收产物的品质和/或提高其营养价值、改善采收产物的贮存稳定性和/或其加工性能。需特别强调的所述特征的其它实例有改善植物对动物和微生物有害物的抵抗力,例如对昆虫、螨虫、植物致病真菌、细菌和/或病毒的抵抗力,以及提高植物对某些除草活性化合物的耐受性。可提出的转基因植物的实例为重要的作物植物,例如谷物(小麦、稻)、玉米、大豆、马铃薯、甜菜、番茄、豌豆以及其它蔬菜品种、棉花、烟草、油菜和果实植物(果实为苹果、梨、柑橘类果实和葡萄),特别强调的是玉米、大豆、马铃薯、棉花、烟草和油菜。尤其强调的特征为通过在植物体内形成毒素,特别是由苏云金杆菌的遗传物质(例如由基因CryIA(a)、CryIA(b)、CryIA(c)、Cry II A、CryIIIA、CryIIIB2、Cry9c、Cry2Ab、Cry3Bb和CryIF及其结合)在植物体内形成的毒素,来提高植物对昆虫、蛛形纲动物、线虫、蛞蝓和腹足类动物的抵抗力(以下简称为“Bt植物”)。还特别强调的特征为通过系统获得性抗性(SAR)、系统素、植物抗毒素、刺激素(elicitor)和抗性基因以及相应的表达蛋白质和毒素来提高植物对真菌、细菌和病毒的抵抗力。尤其强调的其它特征为提高植物对某些除草活性化合物例如咪唑啉酮类、磺酰脲类、草甘膦或草丁膦(phosphinotricin)(例如“PAT”基因)的耐受性。赋予所述所想要特征的基因也可各自在转基因植物体内相互结合存在。可提出的“Bt植物”的实例为市售的商标名称为YIELD(例如玉米、棉花、大豆)、(例如玉米)、(例如玉米)、(棉花)、(棉花)和(马铃薯)的玉米品种、棉花品种、大豆品种和马铃薯品种。可提出的具有除草剂耐受性的植物的实例为市售的商标名称为Roundup(具有草甘膦耐受性,例如玉米、棉花、大豆)、Liberty(具有草丁膦耐受性,例如油菜)、(具有咪唑啉酮耐受性)和(具有磺酰脲耐受性,例如玉米)的玉米品种、棉花品种和大豆品种。还可提出的具有除草剂抗性的植物(以常规的除草剂耐受性方式育种的植物)包括名为的市售品种(例如玉米)。当然,以上叙述也适用于具有所述或待开发的遗传特征的植物栽培种,所述植物栽培种将在未来进行开发和/或上市。
所列植物可以特别有利的方式用本发明的通式I化合物和/或本发明的活性化合物混合物根据本发明进行处理。上述活性化合物或混合物的优选范围也适用于所述植物的处理。特别强调的为用本发明特别提出的化合物或混合物对植物进行处理。
本发明的活性化合物不仅对植物有害物、卫生有害物和贮存产品有害物具有活性,而且在兽医领域对动物寄生虫(体外寄生虫和体内寄生虫)例如硬蜱、软蜱、疥螨、叶螨、蝇(叮咬和吸食)、寄生蝇幼虫、虱、毛虱、羽虱和蚤也具有活性。所述寄生虫包括:
虱目(Anoplurida),例如血虱属(Haematopinus spp.)、毛虱属(Linognathus spp.)、虱属(Pediculus spp.)、Phtirus spp.、管虱属(Solenopotes spp.)
食毛目(Mallophagida)及钝角亚目(Amblycerina)和细角亚目(Ischnocerina),例如毛羽虱属(Trimenopon spp.)、禽虱属(Menoponspp.)、巨羽虱属(Trinoton spp.)、牛羽虱属(Bovicola spp.)、Werneckiella spp.、Lepikentron spp.、畜虱属(Damalina spp.)、嚼虱属(Trichodectes spp.)、猫羽虱属(Felicola spp.)
双翅目及长角亚目(Nematocerina)和短角亚目(Brachycerina),例如伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culexspp.)、蚋属(Simulium spp.)、真蚋属(Eusimulium spp.)、白蛉属(Phlebotomus spp.)、罗蛉属(Lutzomyia spp.)、库蠓属(Culicoidesspp.)、斑虻属(Chrysops spp.)、瘤虻属(Hybomitra spp.)、黄虻属(Atylotus spp.)、虻属(Tabanus spp.)、麻虻属(Haematopota spp.)、Philipomyia spp.、蜂虱蝇属(Braula spp.)、家蝇属(Musca spp.)、齿股蝇属(Hydrotaea spp.)、螫蝇属(Stomoxys spp.)、黑角蝇属(Haematobia spp.)、莫蝇属(Morellia spp.)、厕蝇属(Fannia spp.)、舌蝇属(Glossina spp.)、丽蝇属(Calliphora spp.)、绿蝇属(Luciliaspp.)、金蝇属(Chrysomyia spp.)、污蝇属(Wohlfahrtia spp.)、麻蝇属(Sarcophaga spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypodermaspp.)、胃蝇属(Gasterophilus spp.)、虱蝇属(Hippobosca spp.)、羊虱蝇属(Lipoptena spp.)、蜱蝇属(Melophagus spp.)。
蚤目(Siphonapterida),例如蚤属(Pulex spp.)、栉首蚤属(Ctenocephalides spp.)、客蚤属(Xenopsylla spp.)、角叶蚤属(Ceratophyllus spp.)。
异翅目(Heteropterida),例如臭虫属(Cimex spp.)、锥猎蝽属(Triatoma spp.)、红猎蝽属(Rhodnius spp.)、锥蝽属(Panstrongylusspp.)。
蜚蠊目(Blattarida),例如东方蜚蠊、美洲大蠊、德国蠊、夏柏拉蟑螂属(Supella spp.)。
蜱螨亚纲(Acari或Acarina)及后气门目(Metastigmate)和中气门目(Mesostigmata),例如锐缘蜱属(Argas spp.)、钝缘蜱属(Ornithodorus spp.)、残喙蜱属(Otobius spp.)、硬蜱属(Ixodes spp.)、花蜱属(Amblyomma spp.)、牛蜱属(Boophilus spp.)、革蜱属(Dermacentor spp.)、Haemophysalis spp.、璃眼蜱属(Hyalommaspp.)、扇头蜱属(Rhipicephalus spp.)、皮刺螨属(Dermanyssus spp.)、刺利螨属(Raillietia spp.)、肺刺螨属(Pneumonyssus spp.)、胸刺螨属(Sternostoma spp.)、蜂螨属(Varroa spp.)。
轴螨目(Actinedida)(前气门亚目(Prostigmata))和粉螨目(Acaridida)(无气门亚目(Astigmata)),例如蜂盾螨属(Acarapisspp.)、姬螯螨属(Cheyletiella spp.)、禽螯螨属(Ornithocheyletia spp.)、肉螨属(Myobia spp.)、疮螨属(Psorergates spp.)、蠕形螨属(Demodexspp.)、恙螨属(Trombicula spp.)、Listrophorus spp.、粉螨属(Acarusspp.)、食酪螨属(Tyrophagus spp.)、嗜木螨属(Caloglyphus spp.)、颈下螨属(Hypodectes spp.)、翅螨属(Pterolichus spp.)、痒螨属(Psoroptes spp.)、皮螨属(Chorioptes spp.)、耳疥螨属(Otodectesspp.)、疥螨属(Sarcoptes spp.)、耳螨属(Notoedres spp.)、疙螨属(Knemidocoptes spp.)、气囊螨属(Cytodites spp.)、鸡雏螨属(Laminosioptes spp.)。
本发明的式(I)活性化合物也适用于防治侵袭以下动物的节肢动物:农业生产家畜,例如黄牛、绵羊、山羊、马、猪、驴、骆驼、水牛、兔、家鸡、火鸡、鸭、鹅、蜜蜂,其它玩赏动物,例如狗、猫、笼鸟、观赏鱼,以及所谓的试验动物,例如仓鼠、豚鼠、大鼠和小鼠。通过防治所述节肢动物,应减少死亡和(肉、奶、毛、皮、蛋、蜜等的)产量降低的情况,从而可通过使用本发明的化合物使畜牧更经济、更简便。
本发明的活性化合物通过下述已知方式用于兽医领域和畜牧中:通过例如片剂、胶囊剂、口服饮剂、兽用顿服药、颗粒剂、膏剂、丸剂、喂服(feed-through)法、栓剂的方式进行肠内给药,通过例如注射(肌内、皮下、静脉、腹膜内等)、植入进行肠外给药,可鼻部给药,通过例如浸泡或沐浴、喷雾、泼浇和点滴、清洗、撒粉的形式,以及借助于包括活性化合物的模型制品、例如项圈、耳标、尾标、肢体缚带(limb band)、笼头、标识器等进行皮肤给药。
用于家畜、家禽、玩赏动物等时,式(I)的活性化合物可作为包括1至80重量%的活性化合物的制剂(例如粉剂、乳剂、可流动组合物)直接使用或稀释100至10000倍后使用,或可以化学药浴剂(chemicalbath)形式使用。
而且,已发现本发明的化合物还对毁坏工业材料的昆虫具有强杀昆虫作用。
以实例并且优选但不受任何限制的方式可提出以下昆虫:
甲虫,例如北美家天牛(Hylotrupes bajulus)、Chlorophoruspilosis、家具窃蠹(Anobium punctatum)、报死窃蠹(Xestobiumrufovillosum)、梳角细脉窃蠹(Ptilinus pecticornis)、Dendrobiumpertinex、松窃蠹(Ernobius mollis)、Priobium carpini、褐粉蠹(Lyctusbrunneus)、非洲粉蠹(Lyctus africanus)、南方粉蠹(Lyctusplanicollis)、栎粉蠹(Lyctus linearis)、柔毛粉蠹(Lyctus pubescens)、Trogoxylon aequale、鳞毛粉蠹(Minthes rugicollis)、材小蠹种(Xyleborus spec.)、Tryptodendron spec.、咖啡黑长蠹(Apatemonachus)、槲长蠹(Bostrychus capucins)、褐异翅长蠹(Heterobostrychus brunneus)、棘长蠹种(Sinoxylon spec.)、竹长蠹(Dinoderus minutus);
革翅目昆虫(Hymenopteron),例如大树蜂(Sirex juvencus)、枞大树蜂(Urocerus gigas)、泰加大树蜂(Urocerus gigas taignus)、Urocerus augur;
白蚁,例如欧洲木白蚁(Kalotermes flavicollis)、麻头堆砂白蚁(Cryptotermes brevis)、灰点异白蚁(Heterotermes indicola)、欧美散白蚁(Reticulitermes flavipes)、桑特散白蚁(Reticulitermessantonensis)、南欧网纹白蚁(Reticulitermes lucifugus)、达尔文澳白蚁(Mastotermes darwiniensis)、内华达古白蚁(Zootermopsisnevadensis)、家白蚁(Coptotermes formosanus);
蠹虫(Bristletail),例如衣鱼(Lepisma saccharina)。
本发明中工业材料的含义应理解为非活体(non-living)材料,例如,优选为塑料、粘合剂、胶料、纸张和板材、皮革、木材和木材制品和涂料。
即用的组合物,如果合适,还可包括杀虫剂;并且如果合适,还可包括一种或多种杀菌剂。
对于可能的其它添加剂,可提及上述的杀虫剂和杀菌剂。
本发明的化合物可同样被用于保护与咸水或微咸水接触的物体,例如船体、筛、网、建筑物、系泊设备及信号系统,以防产生污垢。
在家庭、卫生和储存产品保护中,活性化合物亦适于防治封闭空间内发现的有害动物,特别是昆虫、蛛形纲动物和螨虫,所述封闭空间例如住所、工厂车间、办公室、交通工具舱室等。它们可单独或与其他活性化合物和助剂结合用于防治所述害虫的家用杀虫产品中。它们对敏感和抗性物种以及全部发育阶段均具有活性。所述有害物包括:
蝎目(Scorpionidea),例如地中海黄蝎(Buthus occitanus)。
蜱螨目(Acarina),例如波斯锐缘蜱(Argas persicus)、鸽锐缘蜱(Argas reflexus)、苔螨亚种(Bryobia ssp.)、鸡皮刺螨(Dermanyssusgallinae)、家嗜甜螨(Glyciphagus domesticus)、非洲钝缘蜱(Ornithodorus moubat)、血红扇头蜱(Rhipicephalus sanguineus)、阿氏真恙螨(Trombicula alfreddugesi)、Neutrombicula autumnalis、特嗜皮螨(Dermatophagoides pteronissimus)、法嗜皮螨(Dermatophagoides forinae)。
蜘蛛目(Araneae),例如捕鸟蛛(Aviculariidae)、圆蛛(Araneidae)。
盲蛛目(Opiliones),例如螯蝎(Pseudoscorpiones chelifer)、Pseudoscorpiones cheiridium、长踦盲蛛(Opiliones phalangium)。
等足目,例如栉水虱、球鼠妇。
倍足目,例如Blaniulus guttulatus、山蛩虫(Polydesmus spp.)。
唇足目,例如地蜈蚣(Geophilus spp.)。
衣鱼目(Zygentoma),例如栉衣鱼属(Ctenolepisma spp.)、衣鱼、盗火虫(Lepismodes inquilinus)。
蜚蠊目,例如东方蜚蠊、德国蠊、亚洲蠊(Blattella asahinai)、马德拉蜚蠊、角腹蠊属(Panchlora spp.)、木蠊属(Parcoblatta spp.)、澳洲大蠊(Periplaneta australasiae)、美洲大蠊、大褐大蠊(Periplanetabrunnea)、烟色大蠊(Periplaneta fuliginosa)、棕带蜚蠊(Supellalongipalpa)。
跳跃亚目(Saltatoria),例如家蟋。
革翅目,例如欧洲球螋。
等翅目,例如木白蚁属(Kalotermes spp.)、散白蚁属。
啮虫目(Psocoptera),例如Lepinatus spp.、粉啮虫属(Liposcelisspp.)。
鞘翅目,例如圆皮蠹属、毛皮蠹属、皮蠹属、长头谷盗(Latheticusoryzae)、隐跗郭公虫属(Necrobia spp.)、蛛甲属、谷蠹、谷象(Sitophilusgranarius)、米象(Sitophilus oryzae)、玉米象(Sitophilus zeamais)、药材甲(Stegobium paniceum)。
双翅目,例如埃及伊蚊(Aedes aegypti)、白纹伊蚊(Aedesalbopictus)、带喙伊蚊(Aedes taeniorhynchus)、按蚊属、红头丽蝇、高额麻虻(Chrysozona pluvialis)、五带淡色库蚊(Culexquinquefasciatus)、尖音库蚊(Culex pipiens)、环喙库蚊(Culextarsalis)、果蝇属(Drosophila spp.)、夏厕蝇(Fannia canicularis)、家蝇(Musca domestica)、白蛉属、Sarcophaga carnaria、蚋属、厩螫蝇(Stomoxys calcitrans)、欧洲大蚊。
鳞翅目,例如小蜡螟(Achroia grisella)、大蜡螟、印度谷螟(Plodiainterpunctella)、木塞谷蛾(Tinea cloacella)、袋谷蛾、幕谷蛾。
蚤目,例如犬栉首蚤(Ctenocephalides canis)、猫栉首蚤(Ctenocephalides felis)、人蚤(Pulex irritans)、穿皮潜蚤(Tungapenetrans)、印鼠客蚤。
膜翅目,例如广布弓背蚁(Camponotus herculeanus)、黑臭蚁(Lasius fuliginosus)、黑蚁(Lasius niger)、Lasius umbratus、小家蚁、Paravespula spp.、铺道蚁(Tetramorium caespitum)。
虱目(Anoplura),例如头虱(Pediculus humanus capitis)、体虱(Pediculus humanus corporis)、瘿绵蚜属、Phylloera vastatrix、阴虱(Phthirus pubis)。
异翅目,例如热带臭虫(Cimex hemipterus)、温带臭虫(Cimexlectularius)、长红猎蝽(Rhodinus prolixus)、侵扰锥猎蝽(Triatomainfestans)。
在家用杀虫剂领域,它们可单独使用或者与其它合适的活性化合物结合使用,上述合适的活性化合物例如磷酸酯、氨基甲酸酯、拟除虫菊酯、新烟碱类、生长调节剂或来自其它已知的杀虫剂种类的活性化合物。
它们可以以下产品的形式使用:气雾剂、无压喷雾(pressure-freespray)产品例如泵及雾化器(atomizer)喷雾、自动弥雾系统、烟雾剂、泡沫剂、凝胶剂、具有由纤维素或聚合物制得的蒸发片(evaporatortablet)的蒸发产品、液体蒸发剂、凝胶和薄膜蒸发剂、推进剂驱动的蒸发剂、无动力(energy-free)或无源(passive)蒸发系统、捕蛾纸、捕蛾袋和捕蛾胶,以及作为颗粒剂或粉末剂用于抛撒的饵料中或毒饵站(bait station)中。
本发明的活性化合物的制备和使用通过以下实施例说明。
制备实施例
实例(I-1) 方法A(α)
首先,将0.545g(2mmol)化合物II加入50ml二氯甲烷中,室温下加入0.223g(2.2mmol)三乙胺,在0-10℃下逐滴加入0.447g(2.1mmol)金刚烷基乙酰氯,并将混合物在室温下搅拌过夜。为进行后处理,将混合物用稀柠檬酸和5%浓度的NaOH萃取,干燥有机相,通过柱色谱法(硅胶柱,二氯甲烷)浓缩和纯化有机相。
产率:0.656g(理论值的73%),logP=6.94
实例(I-2) 方法A(γ)
首先将0.5g(3.42mmol)乙酰乙酸二乙二醇缩酮加入30ml乙腈中,加入1.327g(10.26mmol)N,N-二异丙基乙胺,室温下加入1.045g(4.11mmol)双(2-氧代-3-噁唑烷基)膦酰氯(BOP-Cl),将该混合物搅拌20min,逐滴加入1.118g(4.11mmol)化合物II,该混合物在室温下搅拌过夜,并用柱色谱法(硅胶,环己烷/乙酸乙酯)浓缩和纯化该混合物。
产率:0.117g(理论值的9%),logP=3.85
实例(I-3)与实例(I-1)类似地获得
实例(I-4)与实例(I-2)类似地获得
实例(I-5)
室温下,将66mg(0.5mmol)3-甲氧基-3-甲基丁酸、0.17ml(1.2mmol)三乙胺、136mg(0.5mmol)化合物II和153mg(0.6mmol)2-氯-1-甲基氯化吡啶于5ml四氢呋喃中搅拌过夜,并将混合物通过柱色谱法(硅胶,环己烷/乙酸乙酯)浓缩和纯化。
产率:149mg(理论值的70%),logP=4.45
logP值的确定
表格中给出的logP值按照EEC Directive 79/831附录V.A8使用反相柱(C 18)HPLC(高效液相色谱)确定。温度:43℃。
测定中使用的流动相处于酸性范围(pH2.3)内:0.1%的磷酸水溶液、乙腈;线性梯度从10%的乙腈至90%的乙腈。
采用logP值已知的无支链的烷-2-酮(具有3至16个碳原子)进行校正(用保留时间通过两种连续烷酮之间的线性内插法来确定logP值)
λ最大值(lambda max value)在采用200nm至400nm的UV光谱的色谱信号最大值中确定。
实施例1
二斑叶螨(Tetranychus urticae,TETRUR RAUS)
溶剂:7重量份的二甲基甲酰胺
乳化剂:10重量份的烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并将浓液用含有乳化剂的水稀释至所需浓度。
用所需浓度的活性化合物制剂喷洒被混合种群的抗性二斑叶螨(Tetranychus urticae,抗性)侵染的菜豆(Phaseolus vulgaris)。
经过所需时间后,确定以%计的灭杀率。100%表示已杀死所有叶螨;0%表示无叶螨被杀死。
该试验中,例如制备实施例的以下化合物在浓度为5ppm时与现有技术WO 00/42850的实施例1(螺甲螨酯)相比显示出优越的活性:I-3(97%),对比于现有技术中的30%。
实施例2
猿叶虫试验(PHAECO喷洒处理)
溶剂:78.0重量份丙酮
1.5重量份二甲基甲酰胺
乳化剂:0.5重量份烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并将浓液用含有乳化剂的水稀释至所需浓度。
用所需浓度的活性化合物制剂喷洒大白菜(Brassica pekinensis)的圆叶片,并在其变干后,接入辣根猿叶甲(Phaedon cochleariae)幼虫。
经过所需时间后,确定以%计的药效。100%表示所有甲虫幼虫被杀死;0%表示无甲虫幼虫被杀死。
该试验中,例如制备实施例的以下化合物在施用率为100g/ha时与现有技术WO 00/42850的实施例1(螺甲螨酯)相比显示出优越的活性:I-2(67%),对比于现有技术的33%。
实施例3
西花蓟马(Frankliniella occidentalis)(FRANOC喷洒处理)
溶剂:78重量份丙酮
1.5重量份二甲基甲酰胺
乳化剂:0.5重量份烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并将浓液用含有乳化剂的水稀释至所需浓度。如果需要加入铵盐,则铵盐在各个制剂溶液稀释后通过移液管以1000ppm的浓度加入。
用所需深度的活性化合物制剂喷洒被混合的蓟马种群(Frankliniella occidentalis)侵染的大豆(Phaseolus vularis)圆叶片。
经过所需时间后,确定以%计的药效。100%表示所有蓟马被杀死;0%表示无蓟马被杀死。
该试验中,例如制备实施例的以下化合物在施用率为100g/ha时与现有技术WO 00/42850的实施例1(螺甲螨酯)相比显示出优越的活性:I-2(63%),对比于现有技术中的0%;
在施用率为500g/ha时与现有技术WO 00/42850的实施例1(螺甲螨酯)相比显示出优越的活性:I-1(80%),对比于现有技术中的0%。
实施例4
桃蚜试验(MYZUPE喷洒处理)
溶剂:7重量份二甲基甲酰胺
乳化剂:2重量份烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并将浓液用含有乳化剂的水稀释至所需浓度。如果需要加入铵盐、渗透剂、或铵盐和渗透剂,则这些物质在各个制剂溶液稀释后通过移液管以1000ppm的浓度加入。
将被绿桃蚜(Myzus persicae)严重侵染的大白菜(Brassicapekinensis)叶片通过浸入所需浓度的活性化合物制剂中而进行处理。
经过所需时间后,确定以%计的灭杀率。100%表示已杀死所有蚜虫;0%表示无蚜虫被杀死。
该试验中,例如制备实施例的以下化合物与现有技术相比显示出优越的活性:见表
实施例5
叶螨(Tetranychus)试验;OP抗性/浸渍处理(TETRUR)
溶剂:7重量份的二甲基甲酰胺
乳化剂:2重量份的烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并将浓液用含有乳化剂的水稀释至所需浓度。如果需要加入铵盐、渗透剂、或铵盐和渗透剂,则这些物质在各个制剂溶液稀释后通过移液管以1000ppm的浓度加入。
被混合种群的抗性二斑叶螨(Tetranychus urticae,抗性)侵染的菜豆(Phaseolus vulgaris)通过浸入所需浓度的活性化合物制剂进行处理。
经过所需时间后,确定以%计的药效。100%表示已杀死所有叶螨;0%表示无叶螨被杀死。
该试验中,例如制备实施例的以下化合物与现有技术相比显示出优越的活性:见表
Claims (7)
3.权利要求1的式(I-3)化合物用于制备农药的用途。
4.农药,其特征在于其包括权利要求1的式(I-3)化合物。
5.防治动物有害物的用于非治疗目的的方法,其特征在于使权利要求1的式(I-3)化合物作用于有害物和/或其生境。
6.权利要求1的式(I-3)化合物用于防治动物有害物的非治疗目的的用途。
7.制备农药的方法,其特征在于将权利要求1的式(I-3)化合物与填充剂和/或表面活性剂混合。
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PCT/EP2008/000084 WO2008083950A2 (de) | 2007-01-12 | 2008-01-09 | Spirocyclische tetronsäure-derivative |
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EP2020413A1 (de) | 2007-08-02 | 2009-02-04 | Bayer CropScience AG | Oxaspirocyclische-spiro-substituierte Tetram- und Tetronsäure-Derivate |
TW201031327A (en) | 2008-11-14 | 2010-09-01 | Bayer Cropscience Ag | Active compound combinations having insecticidal and acaricidal properties |
BRPI1008949B1 (pt) | 2009-03-11 | 2018-07-10 | Bayer Intellectual Property Gmbh | Cetoenóis haloalquilmetilenóxi-fenil-substituídos e seu uso, composição, seu uso e seu método de produção, métodos para combate de pestes animais e/ou crescimento de plantas indesejadas |
CN102439013B (zh) | 2009-05-19 | 2015-03-18 | 拜尔农作物科学股份公司 | 螺杂环特窗酸衍生物 |
ES2700996T3 (es) | 2010-02-10 | 2019-02-20 | Bayer Cropscience Ag | Cetoenoles cíclicos sustituidos con bifenilo |
DE102010008642A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
DE102010008643A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
DE102010008644A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
DE102011011040A1 (de) | 2011-02-08 | 2012-08-09 | Bayer Pharma Aktiengesellschaft | (5s,8s)-3-(4'-Chlor-3'-fluor-4-methylbiphenyl-3-yl)-4-hydroxy-8-methoxy-1-azaspiro[4.5]dec-3-en-2-on (Verbindung A) zur Therapie |
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CN109673643A (zh) * | 2018-08-21 | 2019-04-26 | 青岛瀚生生物科技股份有限公司 | 农用杀虫组合物及其应用 |
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ZA200904745B (en) | 2010-09-29 |
TW200836630A (en) | 2008-09-16 |
CL2008000079A1 (es) | 2008-05-09 |
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JP5300740B2 (ja) | 2013-09-25 |
ES2525481T3 (es) | 2014-12-23 |
PT2111398E (pt) | 2014-12-17 |
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