CN101188936A - 作为抗寄生虫药的1-苯基三唑的衍生物 - Google Patents
作为抗寄生虫药的1-苯基三唑的衍生物 Download PDFInfo
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- CN101188936A CN101188936A CNA2006800195501A CN200680019550A CN101188936A CN 101188936 A CN101188936 A CN 101188936A CN A2006800195501 A CNA2006800195501 A CN A2006800195501A CN 200680019550 A CN200680019550 A CN 200680019550A CN 101188936 A CN101188936 A CN 101188936A
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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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
Abstract
本发明涉及式(I)化合物或其对映体或盐,其中X为氯或溴;Y为氯或三氟甲基;以及A和B为氢或甲基,条件是A或B之一必须为甲基;式(I)化合物在防治昆虫或螨虫和处理、防治、预防或保护动物以防寄生虫侵袭或侵染中的用途以及包含式(I)化合物的组合物。
Description
本发明涉及用于防治昆虫或螨虫的式(I)化合物或其对映体或盐:
其中
X为氯或溴;
Y为氯或三氟甲基;和
A和B为氢或甲基,条件是A或B之一必须为甲基。
本发明还提供了防治昆虫和螨虫的方法,其中使昆虫或螨虫或其食物供应源、栖息地或繁殖地与杀虫有效量的式I化合物或组合物接触。
此外,本发明还涉及一种保护生长植物以防昆虫或螨虫侵袭或侵染的方法,其中向植物的叶面或它们生长的土壤或水体施用杀虫有效量的组合物或式I化合物。
本发明还提供了一种处理、防治、预防或保护动物以防寄生虫侵袭或侵染的方法,包括以口服、局部或胃肠外方式向动物给予或施用杀寄生虫有效量的组合物或式I化合物。
本发明还提供了一种制备用于处理、防治、防止或保护温血动物或鱼类以防昆虫和螨虫侵袭或侵染的组合物的方法,该组合物包含杀虫有效量的式I化合物。
尽管目前可以买到市售杀虫剂和杀螨剂,但仍然存在对作物、家畜、宠物和人类的损害。因此,仍然需要进行研究以提供新的且更有效的杀虫剂和杀螨剂。
因此,本发明的目的是提供新的杀虫和杀螨化合物,用于防治昆虫或螨虫的新组合物和新方法。
我们发现这些目的由式I化合物和组合物实现。
1-苯基三唑尤其已经描述于EP-A 957 094和EP-A 285 893中。然而,这些化合物的杀虫和杀螨性能并不总是令人满意。
因此,本发明的目的是提供新的1-苯基三唑,它们对昆虫和螨虫具有增强的防治性能。
因此,发现了式I的1-苯基-1,2,4-三唑,它们在环丙基环的1位和/或三唑环的5位具有甲基。
EP-A 957 094公开了可以带有任选取代的环丙基环的1-(2-卤代芳基)唑类,其中芳基可以是取代的苯基且唑类可以是1,2,4-三唑。但没有提到在环丙基环或三唑环上连接甲基的有利效果。
EP-A 285 893公开了1-苯基-(1,2,4-三唑),其中在宽范围的取代基中,该三唑在3位上可以带有甲基取代的环丙基,但优选烷基或卤代烷基,且在5位被任选取代,优选被氨基衍生基团取代。EP-A 285 893没有公开本发明的1-苯基三唑,也没有暗示在环丙基环和/或三唑环上连接甲基的有利效果。
取决于取代方式,式I化合物可能含有手性中心,此时它们以对映体混合物存在。本发明的主题不仅仅是包含这些混合物的组合物,还有包含纯对映体的那些。
式I化合物可以通过使式II化合物与氧化剂反应而合成:
其中R为甲基、乙基或三甲基甲硅烷基。
合适的氧化剂例如为氧化铅(IV)(PbO2)、次氯酸盐(例如NaOCl)和二氯二氰基苯醌(DDQ)。
特别优选二氯二氰基苯醌(DDQ)。
该反应通常在-20℃至50℃,优选-5℃至25℃(室温)的温度下在惰性有机溶剂中在碱存在下进行。
合适的溶剂是芳族烃类,如甲苯、邻二甲苯、间二甲苯和对二甲苯,脂族烃类,如戊烷、己烷、环己烷和石油醚,卤代烃类,如二氯甲烷、氯仿和氯苯,醚类,如乙醚、二异丙基醚、叔丁基甲基醚、二烷、四氢呋喃、二甘醇二甲醚或茴香醚,腈类,如乙腈和丙腈,还有二甲亚砜、二甲基甲酰胺和二甲基乙酰胺。特别优选芳族烃类。还可以使用所述溶剂的混合物。
合适的碱是有机碱,如叔胺,如三甲胺、三乙胺、二异丙基乙基胺、N-甲基哌啶和吡啶。取代的吡啶例如为可力丁、卢剔啶和4-二甲氨基吡啶,以及双环胺类,如喹啉或异喹啉。其他合适的碱是无机化合物如碱金属氢氧化物和碱土金属氢氧化物,例如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙,碱金属氧化物和碱土金属氧化物,例如氧化锂、氧化钠、氧化钾、氧化钙和氧化镁,碱金属碳酸盐和碱土金属碳酸盐,例如碳酸锂、碳酸钾和碳酸钙,破金属碳酸氢盐,例如碳酸氢钠,碱金属醇盐和碱土金属醇盐,例如甲醇钠、乙醇钠、乙醇钾、叔丁醇钾和二甲氧基镁。特别优选吡啶和取代吡啶。还可以使用所述碱的混合物。
碱通常以等摩尔量、过量使用或用作溶剂。
式II化合物可以根据EP-A 604 798所述程序得到。
对于式I化合物的意欲应用,特别优选取代基的下列含义,在每种情况下单独或组合:
优选其中X为氯的式I化合物。
此外,优选其中Y为三氟甲基的式I化合物。
还优选其中A为甲基的式I化合物。
此外,优选其中B为甲基的式I化合物。
特别优选其中A为甲基且X为氯的式I化合物。
还特别优选其中B为甲基且X为氯的式I化合物。
还特别优选其中A和B各自为甲基的式I化合物。
特别优选下列化合物:1)1-(2,6-二氯-4-三氟甲基苯基)-3-(1-甲基-2,2-二氯环丙基)-5-甲基-1,2,4-三唑和2)1-(2,6-二氯-4-三氟甲基苯基)-3-(2,2-二氯环丙基)-5-甲基-1,2,4-三唑。
本发明最优选的化合物是1-(2,6-二氯-4-三氟甲基苯基)-3-(1-甲基-2,2-二氯环丙基)-5-甲基-1,2,4-三唑。
式I化合物适于在作物保护中有效防治昆虫和螨虫以及防治非作物害虫。
式I化合物尤其适于有效防治下列害虫:
鳞翅目昆虫(鳞翅目(Lepidoptera)),例如小地老虎(Agrotis ypsilon)、黄地老虎(Agrotis segetum)、木棉虫(Alabama argillacea)、黎豆夜蛾(Anticarsiagemmatalis)、Argyresthia conjugella、叉纹夜蛾(Autographa gamma)、树尺蠖(Bupalus piniarius)、Cacoecia murinana、Capua reticulana、Cheimatobia brumata、云杉色卷蛾(Choristoneura fumiferana)、Choristoneura occidentalis、二化螟(Cirphis unipuncta)、苹果小卷蛾(Cydiapomonella)、松毛虫(Dendrolimus pini)、Diaphania nitidalis、西南玉米杆草螟(Diatraea grandiosella)、埃及钻夜蛾(Earias insulana)、南美玉米苗斑螟(Elasmopalpus lignosellus)、女贞细卷蛾(Eupoecilia ambiguella)、Evetriabouliana、Feltia subterranea、蜡螟(Galleria mellonella)、李小食心虫(Grapholitha funebrana)、梨小食心虫(Grapholitha molesta)、棉铃虫(Heliothis armigera)、烟芽夜蛾(Heliothis virescens)、玉米穗虫(Heliothiszea)、菜螟(Hellula undalis)、Hibernia defoliaria、美国白蛾(Hyphantriacunea)、苹果巢蛾(Hyponomeuta malinellus)、番茄虫蛾(Keiferialycopersicella)、Lambdina fiscellaria、甜菜夜蛾(Laphygma exigua)、咖啡潜叶蛾(Leucoptera coffeella)、旋纹潜蛾(Leucoptera scitella)、Lithocolletisblancardella、葡萄浆果小卷蛾(Lobesia botrana)、甜菜网螟(Loxostegesticticalis)、舞毒蛾(Lymantria dispar)、模毒蛾(Lymantria monacha)、桃潜蛾(Lyonetia clerkella)、黄褐天幕毛虫(Malacosoma neustria)、甘蓝夜蛾(Mamestra brassicae)、黄杉毒蛾(Orgyia pseudotsugata)、玉米螟(Ostrinianubilalis)、小眼夜蛾(Panolis flammea)、棉花红铃虫(Pectinophoragossypiella)、疆夜蛾(Peridroma saucia)、圆掌舟蛾(Phalera bucephala)、马铃薯麦蛾(Phthorimaea operculella)、柑桔潜叶蛾(Phyllocnistis citrella)、欧洲粉蝶(Pieris brassicae)、苜蓿绿夜蛾(Plathypena scabra)、菜蛾(Plutellaxylostella)、大豆夜蛾(Pseudoplusia includens)、Rhyacionia frustrana、Scrobipalpula absoluta、麦蛾(Sitotroga cerealella)、葡萄卷叶蛾(Sparganothis pilleriana)、草地夜蛾(Spodoptera frugiperda)、海灰翅夜蛾(Spodoptera littoralis)、斜纹夜蛾(Spodoptera litura)、Thaumatopoeapityocampa、绿色橡木飞蛾(Tortrix viridana)、粉纹夜蛾(Trichoplusia ni)和Zeiraphera canadensis;
甲虫(鞘翅目(Coleoptera)),例如梨窄吉丁(Agrilus sinuatus)、直条叩头虫(Agriotes lineatus)、暗色叩头虫(Agriotes obscurus)、Amphimallussolstitialis、Anisandrus dispar、墨西哥棉铃象(Anthonomus grandis)、苹花象(Anthonomus pomorum)、Aphthona euphoridae、Athoushaemorrhoidalis、甜菜隐食甲(Atomaria linearis)、纵坑切梢小蠹(Blastophagus piniperda)、Blitophaga undata、蚕豆象(Bruchusrufimanus)、豌豆象(Bruchus pisorum)、欧洲兵豆象(Bruchus lentis)、苹卷象(Byctiscus betulae)、甜菜大龟甲(Cassida nebulosa)、Cerotomatrifurcata、金花金龟(Cetonia aurata)、白菜籽龟象(Ceuthorrhynchusassimilis)、芫菁龟象(Ceuthorrhynchus napi)、甜菜胫跳甲(Chaetoenematibialis)、Conoderus vespertinus、石刁柏负泥虫(Crioceris asparagi)、Ctenicera ssp.、长角叶甲(Diabrotica longicornis)、Diabroticasemipunctata、Diabrotica 12-punctata、南美叶甲(Diabrotica speciosa)、玉米根叶甲(Diabrotica virgifera)、墨西哥豆瓢虫(Epilachna varivestis)、烟草跳甲(Epitrix hirtipennis)、棉灰蒙象变种(Eutinobothrus brasiliensis)、欧洲松树皮象(Hylobius abietis)、埃及苜蓿叶象(Hypera brunneipennis)、紫苜蓿叶象(Hypera postica)、云杉八齿小蠹(Ips typographus)、烟草负泥虫(Lema bilineata)、黑角负泥虫(Lema melanopus)、马铃薯叶甲(Leptinotarsadecemlineata)、Limonius californicus、稻水象甲(Lissorhoptrusoryzophilus)、Melanotus communis、油菜露尾甲(Meligethes aeneus)、大栗鳃金龟(Melolontha hippocastani)、五月鳃金龟(Melolontha melolontha)、水稻负泥虫(Oulema oryzae)、葡萄黑耳喙象(Ortiorrhynchus sulcatus)、草莓根象甲(Otiorrhynchus ovatus)、辣根猿叶甲(Phaedon cochleariae)、梨树叶象(Phyllobius pyri)、Phyllotreta chrysocephala、食叶鳃金龟属(Phyllophaga sp.)、庭园发丽金龟(Phyllopertha horticola)、大豆淡足跳甲(Phyllotreta nemorum)、黄曲条菜跳甲(Phyllotreta striolata)、日本金龟子(Popillia japonica)、豌豆叶象(Sitona lineatus)和谷象(Sitophilus granaria),蝇、蚊(双翅目(Diptera)),例如埃及伊蚊(Aedes aegypti)、白纹伊蚊(Aedesalbopictus)、剌扰伊蚊(Aedes vexans)、墨西哥果蝇(Anastrepha ludens)、五斑按蚊(Anopheles maculipennis)、Anopheles crucians、白足按蚊(Anopheles albimanus)、冈比亚按蚊(Anopheles gambiae)、Anophelesfreeborni、海南岛白踝按蚊(Anopheles leucosphyrus)、云南微小按蚊(Anopheles minimus)、四斑按蚊(Anopheles quadrimaculatus)、红头丽蝇(Calliphora vicina)、地中海实蝇(Ceratitis capitata)、蛆症金蝇(Chrysomyabezziana)、Chrysomya hominivorax、Chrysomya macellaria、鹿蝇(Chrysops discalis)、Chrysops silacea、Chrysops atlanticus、螺旋蝇(Cochliomyia hominivorax)、高粱瘿蚊(Contarinia sorghicola)、嗜人瘤蝇蛆(Cordylobia anthropophaga)、狂怒库蠓(Culicoides furens)、尖音库蚊(Culex pipiens)、斑蚊(Culex nigripalpus)、致倦库蚊(Culexquinquefasciatus)、媒斑蚊(Culex tarsalis)、Culiseta inornata、Culisetamelanura、瓜蝇(Dacus cucurbitae)、油橄榄实蝇(Dacus oleae)、油菜叶瘿蚊(Dasineura brassicae)、Delia antique、麦地种蝇(Delia coarctata)、灰地种蝇(Delia platura)、甘蓝地种蝇(Delia radicum)、Dermatobia hominis、小毛厕蝇(Fannia canicularis)、Geomyza Tripunctata、马蝇(Gasterophilus intestinalis)、刺舌蝇(Glossina morsitans)、须舌蝇(Glossina palpalis)、Glossina fuscipes、胶舌蝇(Glossina tachinoides)、Haematobia irritans、Haplodiplosis equestris、潜蝇属(Hippelates spp.)、花生田灰地种蝇(Hylemyia platura)、纹皮蝇(Hypoderma lineata)、Leptoconops torrens、蔬菜斑潜蝇(Liriomyza sativae)、美国潜叶蝇(Liriomyza trifolii)、Lucilia caprina、铜绿蝇(Lucilia cuprina)、丝光绿蝇(Lucilia sericata)、Lycoria pectoralis、Mansonia titillanus、麦瘿蚊(Mayetiola destructor)、家蝇(Musca domestica)、厩腐蝇(Muscinastabulans)、羊狂蝇(Oestrus ovis)、Opomyza florum、欧洲麦秆蝇(Oscinellafrit)、天仙子泉蝇(Pegomya hysocyami)、葱蝇(Phorbia antiqua)、萝卜蝇(Phorbia brassicae)、麦地种蝇(Phorbia coarctata)、银足白蛉(Phlebotomusargentipes)、Psorophora columbiae、胡萝卜茎蝇(Psila rosae)、Psorophoradiscolor、Prosimulium mixtum、樱桃实蝇(Rhagoletis cerasi)、苹果实蝇(Rhagoletis pomoBella)、赤尾麻蝇(Sarcophaga haemorrhoidalis)、肉蝇属(Sarcophaga)、Simulium vittatum、厩螫蝇(Stomoxys calcitrans)、牛虻(Tabanus bovinus)、Tabanus atratus、红色原虻(Tabanus lineola)、Tabanussimilis、Tipula oleracea和欧洲大蚊(Tipula paludosa),
蓟马(缨翅目(Thysanoptera)),例如兰花蓟马(Dichromothrips corbetti)、Dichromothrips ssp.、烟褐蓟马(Frankliniella fusca)、苜蓿花蓟马(Frankliniella occidentalis)、东方花蓟马(Frankliniella tritici)、桔硬蓟马(Scirtothrips citri)、稻蓟马(Thrips oryzae)、棕榈蓟马(Thrips palmi)和烟蓟马(Thrips tabaci),
白蚁(等翅目(Isoptera)),例如Calotermes flavicollis、Leucotermesflavipes、金黄异白蚁(Heterotermes aureus)、黄肢散白蚁(Reticulitermesflavipes)、美小黑散白蚁(Reticulitermes virginicus)、欧洲散白蚁(Reticulitermes lucifugus)、Termes natalensis和台湾乳白蚁(Coptotermesformosanus),
蟑螂(蜚蠊目(Blattaria)-Blattodea),例如德国小蠊(Blattella germanica)、Blattella asahinae、美洲大蠊(Periplaneta americana)、日本大蠊(Periplaneta japonica)、棕色蜚蠊(Periplaneta brunnea)、Periplanetafuligginosa、澳洲蜚蠊(Periplaneta australasiae)和东方蜚蠊(Blattaorientalis),
臭虫(半翅目(Hemiptera)),例如拟绿蝽(Acrosternum hilare)、玉米长蝽(Blissus leucopterus)、黑斑烟盲蝽(Cyrtopeltis notatus)、棉红蝽(Dysdercus cingulatus)、Dysdercus intermedius、麦扁盾蝽(Eurygasterintegriceps)、烟草蝽(Euschistus impictiventris)、棉红铃喙缘蝽(Leptoglossus phyllopus)、美洲牧草盲蝽(Lygus lineolaris)、牧草盲蝽(Lygus pratensis)、稻绿蝽(Nezara viridula)、甜菜拟网蝽(Piesmaquadrata)、Solubea insularis、Thyanta perditor、Acyrthosiphononobrychis、落叶松球蚜(Adelges laricis)、Aphidula nasturtii、甜菜蚜(Aphis fabae)、草莓根蚜(Aphis forbesi)、苹果蚜(Aphis pomi)、棉蚜(Aphis gossypii)、北美茶簏子蚜(Aphis grossulariae)、希奈德蚜(Aphisschneideri)、卷叶蚜(Aphis spiraecola)、接骨木蚜(Aphis sambuci)、豌豆蚜(Acyrthosiphon pisum)、茄无网蚜(Aulacorthum solani)、银叶粉虱(Bemisia argentifolii)、飞廉短尾蚜(Brachycaudus cardui)、李短尾蚜(Brachycaudus helichrysi)、桃短尾蚜(Brachycaudus persicae)、Brachycaudus prunicola、甘蓝蚜(Brevicoryne brassicae)、Capitophorushorni、Cerosipha gossypii、草莓中瘤钉毛蚜(Chaetosiphon fragaefolii)、茶镳隐瘤蚜(Cryptomyzus ribis)、高加索冷杉椎球蚜(Dreyfusianordmannianae)、云杉椎球蚜(Dreyfusia piceae)、居根西圆尾蚜(Dysaphisradicola)、Dysaulacorthum pseudosolani、车前圆尾蚜(Dysaphisplantaginea)、梨西圆尾蚜(Dysaphis pyri)、蚕豆微叶蝉(Empoascafabae)、桃大尾蚜(Hyalopterus pruni)、Hyperomyzus lactucae、麦长管蚜(Macrosiphum avenae)、大戟长管蚜(Macrosiphum euphorbiae)、蔷薇管蚜(Macrosiphon rosae)、巢莱修尾蚜(Megoura viciae)、Melanaphispyrarius、麦无网蚜(Metopolophium dirhodum)、Myzodes persicae、冬葱瘤额蚜(Myzus ascalonicus)、Myzus cerasi、李瘤蚜(Myzus varians)、黑茶镳子衲长管蚜(Nasonovia ribis-nigri)、稻飞虱(Nilaparvata lugens)、囊柄瘿绵蚜(Pemphigus bursarius)、蔗飞虱(Perkinsiella saccharicida)、忽布疣蚜(Phorodon humuli)、苹木虱(Psylla mali)、梨木虱(Psylla piri)、冬葱瘤蛾蚜(Rhopalomyzus ascalonicus)、玉米蚜(Rhopalosiphum maidis)、禾谷溢管蚜(Rhopalosiphum padi)、苹草缢管蚜(Rhopalosiphum insertum)、Sappaphis mala、Sappaphis mali、麦二叉蚜(Schizaphis graminum)、Schizoneura lanuginosa、麦长管蚜(Sitobion avenae)、白粉虱(Trialeurodes vaporariorum)、桔二叉蚜(Toxoptera aurantiiand)、葡萄根瘤蚜(Viteus vitifolii)、温带臭虫(Cimex lectularius)、热带臭虫(Cimexhemipterus)、Reduvius senilis、Triatoma属和Arilus critatus,蚂蚁、蜜蜂、黄蜂、锯蝇(膜翅目(Hymenoptera)),例如新疆菜叶蜂(Athaliarosae)、切叶蚁(Atta cephalotes)、Atta capiguara、Atta laevigata、Attarobusta、Atta sexdens、Atta texana、举腹蚁属(Crematogaster)、Hoplocampa minuta、Hoplocampa testudinea、小黄家蚁(Monomoriumpharaonis)、热带火蚁(Solenopsis geminate)、红火蚁(Solenopsis invicta)、黑火蚁(Solenopsis richteri)、南方火蚁(Solenopsis xyloni)、红蚂蚁(Pogonomyrmex barbatus)、Pogonomyrmex californicus、Pheidolemegacephala、天鹅绒蚂蚁(Dasymutilla occidentalis)、熊蜂属(Bombus)、大黄蜂(Vespula squamosa)、Paravespula vulgaris、Paravespulapennsylvanica、Paravespula germanica、姬胡蜂(Dolichovespula maculata)、黄边胡蜂(Vespa crabro)、胡蜂(Polistes rubiginosa)、Campodontusfloridanus和阿根廷蚁(Linepithema humile),
蟋蟀、蚱蜢、蝗虫(直翅目(Orthoptera)),例如居屋艾蟋(Acheta domestica)、蝼蛄(Gryllotalpa gryllotalpa)、飞蝗(Locusta migratoria)、双纹黑蝗(Melanoplus bivittatus)、红足黑蝗(Melanoplus femurrubrum)、墨西哥黑蝗(Melanoplus mexicanus)、迁飞黑蝗(Melanoplus sanguinipes)、石栖黑蝗(Melanoplus spretus)、条纹红蝗(Nomadacris septemfasciata)、美洲沙漠蝗(Schistocerca americana)、沙漠蝗(Schistocerca gregaria)、摩洛哥戟纹蝗(Dociostaurus maroccanus)、庭疾灶螽(Tachycines asynamorus)、塞纳加尔小车蝗(Oedaleus senegalensis)、Zonozerus variegatus、非洲蔗蝗(Hieroglyphus daganensis)、Kraussaria angulifera、意大利蝗(Calliptamusitalicus)、澳洲草栖蝗(Chortoicetes terminifera)和褐色拟飞蝗(Locustanapardalina),
蜘蛛纲(Arachnoidea)),如蜘蛛(蜱螨目(Acarina)),例如软蜱科(Argasidae)、硬蜱科(Ixodidae)和疥螨科(Sarcoptidae),如长星形壁虱(Amblyommaamericanum)、热带花蜱(Amblyomma variegatum)、Ambryommamaculatum、波斯锐缘蜱(Argas persicus)、牛壁虱(Boophilus annulatus)、Boophilus decoloratus、微小牛蜱(Boophilus microplus)、Dermacentorsilvarum、安氏革蜱(Dermacentor andersoni)、美洲大革蜱(Dermacentorvariabilis)、Hyalomma truncatum、蓖子硬蜱(Ixodes ricinus)、Ixodesrubicundus、黑脚硬蜱(Ixodes scapularis)、全环硬蜱(Ixodes holocyclus)、太平洋硬蜱(Ixodes pacificus)、Ornithodorus moubata、Ornithodorushermsi、Ornithodorus turicata、柏氏禽刺螨(Ornithonyssus bacoti)、Otobiusmegnini、鸡皮刺螨(Dermanyssus gallinae)、绵羊疥病(Psoroptes ovis)、Rhipicephalus sanguineus、Rhipicephalus appendiculatus、Rhipicephalusevertsi、人疥螨(Sarcoptes scabiei),瘿螨(Eriophyidae)属,如苹果刺锈螨(Aculus schlechtendali)、Phyllocoptrata oleivora和Eriophyes sheldoni;细螨(Tarsonemidae)属,如Phytonemus pallidus和侧多食跗线螨(Polyphagotarsonemus latus);细须螨(Tenuipalpidae)属,如紫红短须螨(Brevipalpus phoenicis);叶螨(Tetranychidae)属,如朱砂叶螨(Tetranychuscinnabarinus)、神泽叶螨(Tetranychus kanzawai)、太平洋叶螨(Tetranychuspacificus)、棉叶螨(Tetranychus telarius)和二点叶螨(Tetranychus urticae),苹果叶螨(Panonychus ulmi)、柑椐叶螨(Panonychus citri)和草地小爪螨(Oligonychus pratensis);蜘蛛目(Araneida),例如毒蜘蛛(Latrodectusmactans)和褐丝蛛(Loxosceles reclusa),
跳蚤(蚤目(Siphonaptera)),例如猫跳蚤(Ctenocephalides felis)、狗跳蚤(Ctenocephalides canis)、印鼠客蚤(Xenopsylla cheopis)、致瘁蚤(Pulexirritans)、穿皮潜蚤(Tunga penetrans)和具带病蚤(Nosopsyllus fasciatus),衣鱼、家衣鱼(缨尾目(Thysanura)),例如西洋衣鱼(Lepisma saccharina)和斑衣鱼(Thermobia domestica),
百足虫(唇足纲(Chilopoda)),例如Scutigera coleoptrata,
千足虫(倍足纲(Diplopoda)),例如Narceus属,
蠼蛸(革翅目(Dermaptera)),例如欧洲球螋(forficula auricularia),虱(毛虱目(Phthiraptera)),例如人头虱(Pediculus humanus capitis)、人体虱(Pediculus humanus corporis)、阴虱(Pthirus pubis)、牛血虱(Haematopinus eurysternus)、猪血虱(Haematopinus suis)、牛颚虱(Linognathus vituli)、Bovicola bovis、鸡虱(Menopon gallinae)、Menacanthus stramineus和Solenopotes capillatus。
此外,式I化合物和含有它们的组合物尤其可以用于防治等翅目、双翅目、蜚蠊目(Blattodea)、膜翅目、蚤目和蜱螨目昆虫。
对于本发明的应用,可以将化合物I转化成常规配制剂,例如溶液、乳液、悬浮液、粉剂、粉末、糊和颗粒。使用形式取决于特定的目的;在任何情况下意欲保证本发明化合物精细和均匀地分布。
配制剂以已知方式制备,例如通过将活性成分与溶剂和/或载体混合而制备,若需要的话使用乳化剂和分散剂。合适的溶剂/助剂主要为:
-水、芳族溶剂(如Solvesso产品、二甲苯)、石蜡(如矿物油馏分)、醇类(如甲醇、丁醇、戊醇、苄醇)、酮类(如环己酮、γ-丁内酯)、吡咯烷酮(NMP、NOP)、乙酸酯(乙二醇二乙酸酯)、二元醇、脂肪酸二甲基酰胺、脂肪酸及脂肪酸酯。原则上还可以使用溶剂混合物。
-载体如磨碎的天然矿物(如高岭土、粘土、滑石、白垩)和磨碎的合成矿物(如高度分散的硅石、硅酸盐);乳化剂如非离子和阴离子乳化剂(如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)以及分散剂如木素亚硫酸盐废液和甲基纤维素。
合适的表面活性剂是木素磺酸、萘磺酸、苯酚磺酸、二丁基萘磺酸的碱金属盐、碱土金属盐和铵盐,烷基芳基磺酸盐,烷基硫酸盐,烷基磺酸盐,脂肪醇硫酸盐,脂肪酸和硫酸化脂肪醇乙二醇醚,还有磺化萘和萘衍生物与甲醛的缩合物,萘或萘磺酸与苯酚的缩合物,辛基酚、壬基酚,烷基苯基聚乙二醇醚,三丁基苯基聚乙二醇醚,三硬脂基苯基聚乙二醇醚,烷基芳基聚醚醇,醇和脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚,乙氧基化聚氧丙烯,月桂醇聚乙二醇醚缩醛,山梨醇酯,木素亚硫酸盐废液和甲基纤维素以及氧化乙烯/氧化丙烯嵌段共聚物。
适于制备可直接喷雾溶液、乳液、糊或油分散体的物质是中沸点到高沸点的矿物油馏分,如煤油或柴油,此外还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃,例如甲苯、二甲苯、石蜡、四氢化萘、烷基化萘或其衍生物、甲醇、乙醇、丙醇、丁醇、环己醇、环己酮、异佛尔酮,强极性溶剂,例如二甲亚砜、N-甲基吡咯烷酮和水。
粉末、撒播用材料和粉剂可以通过将活性物质与固体载体混合或同时研磨而制备。
颗粒如涂覆颗粒、浸渍颗粒和均质颗粒可以通过将活性成分与固体载体粘附而制备。固体载体的实例是矿土如硅胶、硅酸盐、滑石、高岭土、活性粘土(attaclay)、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁;磨碎的合成材料;肥料如硫酸铵、磷酸铵、硝酸铵、尿素;植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉和其它固体载体。
配制剂通常包含0.01-95重量%,优选0.1-90重量%的活性成分。活性成分以90-100%,优选95-100%的纯度(根据NMR谱)使用。
下列为配制剂实例:
1.用水稀释的产品
A水溶性浓缩物(SL、LS)
将10重量份本发明化合物溶于水或水溶性溶剂中。或者,加入湿润剂或其它助剂。活性成分经水稀释溶解。
B分散性浓缩物(DC)
将20重量份本发明化合物溶于环己酮中并加入分散剂如聚乙烯基吡咯烷酮。用水稀释得到分散体。
C可乳化的浓缩物(EC)
将15重量份本发明化合物溶于二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下浓度为5%)。用水稀释得到乳液。D乳液(EW、EO、ES)
将40重量份本发明化合物溶于二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下浓度为5%)。借助乳化机(Ultraturrax)将该混合物引入水中并制成均相乳液。用水稀释得到乳液。
E悬浮液(SC、OD、FS)
在搅拌的球磨机中,将20重量份本发明化合物粉碎并加入分散剂、湿润剂和水或有机溶剂,得到细碎活性成分悬浮液。用水稀释得到稳定的活性成分悬浮液。
F水分散性颗粒和水溶性颗粒(WG、SG)
将50重量份本发明化合物细碎研磨并加入分散剂和湿润剂,借助工业装置(如挤出机、喷雾塔、流化床)将其制成水分散性或水溶性颗粒。用水稀释得到稳定的活性成分分散体或溶液。
G水分散性粉末和水溶性粉末(WP、SP、WS)
将75重量份本发明化合物在转子-定子磨机中研磨并加入分散剂、湿润剂和硅胶。用水稀释得到稳定的活性成分分散体或溶液。
2.不经稀释而施用的产品
H可撒粉粉末(DP、DS)
将5重量份本发明化合物细碎研磨并与95%的细碎高岭土充分混合。这得到可撒粉产品。
I颗粒(GR、FG、GG、MG)
将0.5重量份本发明化合物细碎研磨并结合95.5%载体。现行方法是挤出、喷雾干燥或流化床方法。这得到不经稀释而施用的颗粒。
J ULV溶液(UL)
将10重量份本发明化合物溶于有机溶剂如二甲苯中。这得到不经稀释而施用的产品。
活性成分可以直接、以其配制剂形式或由其制备的使用形式(如可直接喷雾溶液、粉末、凝胶、悬浮液或分散体、乳液、油分散体、糊、可撒粉产品、撒播用材料或颗粒、微胶囊(CS)、丸粒或片剂形式),借助喷雾、雾化、撒粉、撒播或浇灌来使用。使用形式完全取决于意欲的目的;意欲在每种情况下确保本发明活性成分的最佳可能分布。
含水使用形式可通过加入水由乳液浓缩物、糊或可湿性粉末(可喷雾粉末、油分散体)制备。为制备乳液、糊或油分散体,可借助湿润剂、增粘剂、分散剂或乳化剂将该物质直接或溶于油或溶剂中后在水中均化。然而,还可以制备由活性物质、湿润剂、增粘剂、分散剂或乳化剂以及合适的话溶剂或油组成的浓缩物且该浓缩物适于用水稀释。
即用产品中的活性成分浓度可在较宽范围内变化。它们通常为0.0001-10%,优选0.01-1%。
活性成分也可成功用于超低容量法(ULV),其中可以施用包含超过95重量%活性成分的配制剂,或甚至施用不含添加剂的活性成分。
可以向活性成分中加入各种类型的油、润湿剂、辅助剂、除草剂、杀真菌剂、其他农药或杀菌剂,合适的话仅在紧临使用前加入(桶混合)。这些试剂通常与本发明试剂以1∶10-10∶1的重量比混合。
式I化合物通过接触(经由土壤、玻璃、墙壁、床品、地毯、植物部分或动物部分)和摄取(诱饵或植物部分)以及交哺和转移而有效。
优选的施用方法是经由土壤、裂纹和裂缝施用于水体,施用于牧场、粪堆、下水道,施用于水中、地板、墙壁上,或者通过周边喷雾施用和诱饵施用。
根据本发明的优选实施方案,式I化合物经由土壤施用而使用。土壤施用尤其有利地用于对抗蚂蚁、白蚁、蝇、蟋蟀或蟑螂。
根据本发明的另一优选实施方案,为了用于对抗非作物害虫如蚂蚁、白蚁、黄蜂、蝇、蚊子、蟋蟀、蝗虫或蟑螂,将式I化合物制备成诱饵制剂。
诱饵可以是液体、固体或半固体制剂(例如凝胶)。固体诱饵可以制成各种适合相应用途的形状和形式,如颗粒、块、棒、片。液体诱饵可以填充到各种装置中以确保适当施用,例如敞开容器、喷雾装置、液滴供应源或蒸发源。凝胶可以基于含水基质或油性基质且可以按照粘性、水分保留或老化特性根据特定要求配制。
用于组合物中的诱饵是具有足够的吸引力以刺激诸如蚂蚁、白蚁、黄蜂、蝇、蚊子、蟋蟀等的昆虫或蟑螂食用它的产品。该吸引剂可以选自进食刺激剂或伪和/或性信息素。合适的食物刺激剂例如选自动物和/或植物蛋白质(肉-、鱼-或血液膳食,昆虫部分、蟋蟀粉末、蛋黄)、动物和/或植物来源的脂肪和油或单-、低聚-或聚有机糖类,尤其是蔗糖、乳糖、果糖、右旋糖、葡萄糖、淀粉、果胶或甚至糖蜜或蜂蜜,或选自诸如硫酸铵、碳酸铵或乙酸铵的盐。水果、作物、植物、动物、昆虫的新鲜或腐败部分或其特定部分也可以用作进食刺激剂。
已知信息素更具昆虫特异性。特殊信息素描述于文献中并且对本领域熟练技术人员是已知的。
式I化合物的配制剂如气雾剂(例如在喷雾罐中)、油喷雾剂或泵喷雾剂高度适于非专业使用者来防治害虫如蝇、跳蚤、蜱、蚊子、蝗虫或蟑螂。气雾剂配方优选由如下组分组成:活性化合物;溶剂如低级醇(例如甲醇、乙醇、丙醇、丁醇),酮类(例如丙酮、甲基乙基酮),沸程为约50-250℃的链烷烃(例如煤油),二甲基甲酰胺,N-甲基吡咯烷酮,二甲亚砜,芳族烃类如甲苯、二甲苯,水;此外还有助剂,例如乳化剂如山梨糖醇单油酸酯、具有3-7mol氧化乙烯的油基乙氧基化物、脂肪醇乙氧基化物,芳香油如精油,中等脂肪酸与低级醇的酯,芳族羰基化合物;合适的话还有稳定剂如苯甲酸钠,两性表面活性剂,低级环氧化物,原甲酸三乙酯和需要的话推进剂如丙烷、丁烷、氮气、压缩空气、二甲醚、二氧化碳、氧化亚氮或这些气体的混合物。
油喷雾配制剂与气雾剂配方的不同在于没有使用推进剂。
式I化合物及其相应的组合物还可以用于蚊香片和熏蒸片,发烟盒、蒸发器板或长效蒸发器以及扑蛾纸、扑蛾垫或其他与热无关的蒸发器体系中。
用式I化合物及其相应组合物控制由昆虫传播的传染性疾病(例如疟疾、登革热和黄热病,淋巴丝虫病以及利什曼病)的方法也包括处理棚屋和房子的表面、空气喷雾和浸渍窗帘、帐篷、衣物、床品、采蝇网等。施用于纤维、织物、编织物、无纺织物、网状材料或箔以及篷布上的杀虫组合物优选包含包括杀虫剂、任选的驱除剂和至少一种粘合剂的混合物。
窗帘和床品的浸渍在大多数情况下通过将纺织材料浸入杀虫剂的乳液或分散体中或将它们喷雾于床品上而进行。
式I化合物还适于保护种子以及秧苗的根和芽,优选种子,以防土壤害虫。
尤其优选的是保护禾谷类(例如小麦、大麦、黑麦)、油菜(canola)、糖用甜菜、玉米、高粱、向日葵、棉花、稻、豌豆、油菜(colza)、土豆以及菜园作物如稻、小麦、大麦或黑麦的种子。
常规的种子处理配制剂例如包括可流动浓缩物FS、溶液LS、干处理用粉末DS、水分散性粉末WS或淤浆处理用颗粒、水溶性粉末SS和乳液ES。可以在播种之前对种子进行施用,或者直接施用于种子上或者在种子预萌发之后施用。
优选FS配制剂。
用于种子处理的式I化合物的优选FS配制剂包含0.5-80%活性成分,0.05-5%润湿剂,0.5-15%分散剂,0.1-5%增稠剂,5-20%防冻剂,0.1-2%消泡剂,1-20%颜料和/或染料,0-15%粘着剂/粘附剂,0-75%填料/赋形剂和0.01-1%防腐剂。
在种子处理中,式I化合物或包含它的组合物的施用率通常为0.1g-10kg/100kg种子,优选1g-5kg/100kg种子,尤其是1g-2.5kg/100kg种子。对于特定的作物如莴苣,施用率可以更高。
在害虫的防治中,式I化合物或包含它的组合物可以在植物播种之前或之后或者在植物发芽之前或之后通过对种子、植物或土壤喷雾或撒粉而施用。
本发明的另一方面是一种在种子犁沟中用颗粒状配制剂处理种子的方法,该配制剂含有活性化合物或包含它的组合物以及任选一种或多种固体或液体可农用载体和/或任选一种或多种可农用表面活性剂。该方法有利地用于禾谷类、玉米、棉花和向日葵的种子床中。对于禾谷类和玉米,式I化合物的施用率为50-500g/ha。
本发明还涉及植物繁殖产品,尤其是已处理种子,其包含,即涂有和/或含有式I化合物或包含它的组合物。术语“涂有和/或含有”通常是指活性成分在施用时绝大部分处于繁殖材料的表面上,但或多或少的部分活性成分可能渗入繁殖产品中,这取决于施用方法。当(再)种植所述繁殖产品时,它可能吸收活性成分。
种子以0.1g-10kg/100kg种子的量包含本发明化合物或含有它的组合物。
本发明的组合物还可以含有其他活性成分,例如其他农药,杀虫剂,除草剂,肥料如硝酸铵、尿素、钾碱和酸性磷酸盐,植物毒素和植物生长调节剂,安全剂和杀线虫剂。这些额外成分可以与上述组合物依次或结合使用,合适的话还在紧临使用前加入(桶混物)。例如可以在用其他活性成分处理之前或之后用本发明组合物喷雾植物。
可与本发明化合物一起使用的下列农药用来阐述可能的组合,而不施以任何限制:
A.1.有机(硫代)磷酸酯类:高灭磷(acephate)、唑啶磷(azamethiphos)、谷硫磷(azinphos-methyl)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、毒虫畏(chlorfenvinphos)、二嗪农(diazinon)、敌敌畏(dichlorvos)、百治磷(dicrotophos)、乐果(dimethoate)、乙拌磷(disulfoton)、乙硫磷(ethion)、杀螟松(fenitrothion)、倍硫磷(fenthion)、异唑磷(isoxathion)、马拉硫磷(malathion)、甲胺磷(methamidophos)、杀扑磷(methidathion)、甲基一六零五(methyl-parathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、砜吸磷(oxydemeton-methyl)、对氧磷(paraoxon)、一六零五(parathion)、稻丰散(phenthoate)、伏杀磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、甲拌磷(phorate)、辛硫磷(phoxim)、虫螨磷(pirimiphos-methyl)、丙溴磷(profenofos)、丙硫磷(prothiofos)、乙丙硫磷(sulprophos)、杀虫威(tetrachlorvinphos)、特丁磷(terbufos)、三唑磷(triazophos)、敌百虫(trichlorfon);
A.2.氨基甲酸酯类:棉铃威(alanycarb)、涕灭威(aldicarb)、虫威(bendiocarb)、丙硫克百威(benfuracarb)、甲萘威(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、双氧威(fenoxycarb)、呋线威(furathiocarb)、灭虫威(methiocarb)、灭多虫(methomyl)、甲氨叉威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、唑蚜威(triazamate);
A.3.合成除虫菊酯类:丙烯除虫菊(allethrin)、氟氯菊酯(bifenthrin)、氟氯氰菊酯(cyfluthrin)、(RS)氯氟氰菊酯(cyhalothrin)、苯醚氰菊酯(cyphenothrin)、氯氰菊酯(cypermethrin)、甲体氯氰菊酯(alpha-cypermethrin)、乙体氯氰菊酯(beta-cypermethrin)、己体氯氰菊酯(zeta-cypermethrin)、溴氰菊酯(deltamethrin)、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、杀灭菊酯(fenvalerate)、咪炔菊酯(imiprothrin)、氯氟氰菊酯(lambda-cyhalothrin)、氯菊酯(permethrin)、炔酮菊酯(prallethrin)、除虫菊酯(pyrethrin)I和II、灭虫菊(resmethrin)、灭虫硅醚(silafluofen)、氟胺氰菊酯(tau-fluvalinate)、七氟菊酯(tefluthrin)、胺菊酯(tetramethrin)、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin)、丙氟菊酯(profluthrin)、四氟甲醚菊酯(dimefluthrin);
A.4.生长调节剂:a)几丁质合成抑制剂:苯甲酰脲类,如定虫隆(chlorfluazuron)、氟脲杀(diflubenzuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氟丙氧脲(lufenuron)、双苯氟脲(novaluron)、伏虫隆(teflubenzuron)、杀虫隆(triflumuron);噻嗪酮(buprofezin)、茂醚(diofenolan)、噻螨酮(hexythiazox)、特苯唑(etoxazole)、四螨嗪(clofentazine);b)蜕皮激素拮抗剂:例如特丁苯酰肼(halofenozide)、甲氧苯酰肼(methoxyfenozide)、双苯酰肼(tebufenozide)、艾扎丁(azadirachtin);c)保幼激素类似物:例如蚊蝇醚(pyriproxyfen)、蒙五一五(methoprene)、双氧威(fenoxycarb);d)类脂生物合成抑制剂:例如螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)、螺虫乙酯(spirotetramat);
A.5.烟碱受体激动剂/拮抗剂化合物:噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、噻虫嗪(thiamethoxam)、硝胺烯啶(nitenpyram)、吡虫清(acetamiprid)、噻虫啉(thiacloprid);
式Γ1的噻唑化合物:
A.6.GABA拮抗剂化合物:acetoprole、硫丹(endosulfan)、乙虫清(ethiprole)、锐劲特(fipronil)、氟吡唑虫(vaniliprole)、pyrafluprole、pyriprole、式Γ2的苯基吡唑化合物:
A.7.大环内酯杀虫剂:齐墩螨素(abamectin)、甲氨基阿维菌素(emamectin)、米尔螨素(milbemectin)、lepimectin、艾克敌105(spinosad),
A.8.METI I化合物:喹螨醚(fenazaquin)、哒螨酮(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)、flufenerim;
A.9.METI II和III化合物:灭螨醌(acequinocyl)、fluacyprim、灭蚁腙(hydramethylnon);
A.10.分离剂化合物:氟唑虫清(chlorfenapyr);
A.11.氧化磷酸化抑制剂化合物:三环锡(cyhexatin)、杀螨硫隆(diafenthiuron)、杀螨锡(fenbutatin oxide)、克螨特(propargite);
A.12.蜕皮干扰剂(Moulting disruptor)化合物:cryomazine;
A.13.混合功能氧化酶抑制剂化合物:增效醚(piperonyl butoxide);
A.14.钠通道阻断剂化合物:二唑虫(indoxacarb)、氰氟虫胺(metaflumizone);
A.15.其他:benclothiaz、联苯肼酯(bifenazate)、杀螟丹(cartap)、氟啶虫酰胺(flonicamid)、啶虫丙醚(pyridalyl)、拒嗪酮(pymetrozine)、硫、硫环杀(thiocyclam)、氟虫酰胺(flubendiamide)、cyenopyrafen、吡氟硫磷(flupyrazofos)、丁氟螨酯(cyflumetofen)、amidoflumet、式Γ3的氨基异噻唑化合物:
其中Ri为-CH2OCH2CH3或H且Rii为CF2CF2CF3或CH2CH(CH3)3,式Γ4的邻氨基苯甲酰胺(anthranilamide)化合物:
其中A1为CH3、Cl、Br、I,X为C-H、C-Cl、C-F或N,Y’为F、Cl或Br,Y”为氢、F、Cl、CF3,B1为氢、Cl、Br、I、CN,B2为Cl、Br、CF3、OCH2CF3、OCF2H,以及RB为氢、CH3或CH(CH3)2,以及JP 2002 284608、WO 02/89579、WO 02/90320、WO 02/90321、WO 04/06677、WO 04/20399、JP 2004 99597、WO 05/68423、WO 05/68432或WO 05/63694中所述的丙二腈化合物,尤其是丙二腈化合物CF2HCF2CF2CF2CH2C(CN)2CH2CH2CF3(2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(3,3,3-三氟丙基)丙二腈)、CF3(CH2)2C(CN)2CH2(CF2)5CF2H(2-(2,2,3,3,4,4,5,5,6,6,7,7-十二氟庚基)-2-(3,3,3-三氟丙基)丙二腈)、CF3(CH2)2C(CN)2(CH2)2C(CF3)2F(2-(3,4,4,4-四氟-3-三氟甲基丁基)-2-(3,3,3-三氟丙基)丙二腈)、CF3(CH2)2C(CN)2(CH2)2(CF2)3CF3(2-(3,3,4,4,5,5,6,6,6-九氟己基)-2-(3,3,3-三氟丙基)丙二腈)、CF2H(CF2)3CH2C(CN)2CH2(CF2)3CF2H(2,2-二(2,2,3,3,4,4,5,5-八氟戊基)丙二腈)、CF3(CH2)2C(CN)2CH2(CF2)3CF3(2-(2,2,3,3,4,4,5,5,5-九氟戊基)-2-(3,3,3-三氟丙基)丙二腈)、CF3(CF2)2CH2C(CN)2CH2(CF2)3CF2H(2-(2,2,3,3,4,4,4-七氟丁基)-2-(2,2,3,3,4,4,5,5-八氟戊基)丙二腈)和CF3CF2CH2C(CN)2CH2(CF2)3CF2H(2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(2,2,3,3,3-五氟丙基)丙二腈)。
A组的市售化合物可以在其他出版物中的The Pesticide Manual,第13版,British Crop Protection Council(2003)中找到。
式Γ2的硫羰胺及其制备描述于WO 98/28279中。式Γ3的氨基异噻唑化合物及其制备描述于WO 00/06566中。Lepimectin由Agro Project,PJBPublications Ltd,2004年11月已知。Benclothiaz及其制备描述于EP-A1454621中。杀扑磷和对氧磷及其制备描述于Farm Chemicals Handbook,第88卷,Meister Publishing Company,2001中。Acetoprole及其制备描述于WO 98/28277中。氰氟虫胺及其制备描述于EP-A1 462 456中。吡氟硫磷描述于Pesticide Science 54,1988,第237-243页和US 4822779中。Pyrafluprole及其制备描述于JP 2002193709和WO 01/00614中。Pyriprole及其制备描述于WO 98/45274和US 6335357中。Amidoflumet及其制备描述于US 6221890和JP 21010907中。Flufenerim及其制备描述于WO03/007717和WO 03/007718中。丁氟螨酯及其制备描述于WO 04/080180中。
式Γ4的邻氨基苯甲酰胺及其制备描述于WO 01/70671、WO 02/48137、WO 03/24222、WO 03/15518、WO 04/67528、WO 04/33468和WO05/118552中。丙二腈化合物CF2HCF2CF2CF2CH2C(CN)2CH2CH2CF3(2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(3,3,3-三氟丙基)丙二腈)、CF3(CH2)2C(CN)2CH2(CF2)5CF2H(2-(2,2,3,3,4,4,5,5,6,6,7,7-十二氟庚基)-2-(3,3,3-三氟丙基)丙二腈)、CF3(CH2)2C(CN)2(CH2)2C(CF3)2F(2-(3,4,4,4-四氟-3-三氟甲基丁基)-2-(3,3,3-三氟丙基)丙二腈)、CF3(CH2)2C(CN)2(CH2)2(CF2)3CF3(2-(3,3,4,4,5,5,6,6,6-九氟己基)-2-(3,3,3-三氟丙基)丙二腈)、CF2H(CF2)3CH2C(CN)2CH2(CF2)3CF2H(2,2-二(2,2,3,3,4,4,5,5-八氟戊基)丙二腈)、CF3(CH2)2C(CN)2CH2(CF2)3CF3(2-(2,2,3,3,4,4,5,5,5-九氟戊基)-2-(3,3,3-三氟丙基)丙二腈)、CF3(CF2)2CH2C(CN)2CH2(CF2)3CF2H(2-(2,2,3,3,4,4,4-七氟丁基)-2-(2,2,3,3,4,4,5,5-八氟戊基)丙二腈)和CF3CF2CH2C(CN)2CH2(CF2)3CF2H(2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(2,2,3,3,3-五氟丙基)丙二腈)描述于WO05/63694中。
优选与N-R’-2,2-二halo-1-R”环丙烷甲酰胺-2-(2,6-二氯-α,α,α-三氟对甲苯基)腙或N-R’-2,2-二(R)丙酰胺-2-(2,6-二氯-α,α,α-三氟对甲苯基)腙的混合物,其中R’为甲基或乙基,halo为氯或溴,R”为氢或甲基且R为甲基或乙基。
式I化合物与上述农药的某些混合物是协同增效的,即它们含有协同增效有效量的活性混合组分。优选式I化合物与下列农药的协同增效混合物:
此外,对本发明的应用而言尤其优选如下混合物:其中式II化合物选自A.3.组(合成除虫菊酯类)、A.4.组(生长调节剂)、A.5.组(烟碱受体激动剂/拮抗剂化合物)、A.6.组(GABA拮抗剂化合物)、A.7.组(大环内酯杀虫剂)、A.10.组(分离剂化合物)、A.14.组(钠通道阻断剂化合物)或A.15.组(各种杀虫剂化合物)。
最优选如下混合物:其中式II化合物选自由氟氯菊酯、(RS)氯氟氰菊酯、氯氰菊酯、甲体氯氰菊酯、溴氰菊酯、高效氯氟氰菊酯(lamda-cyhalothrin)、氯菊酯组成的A-1组;氟虫脲、氟铃脲、伏虫隆、双苯氟脲;噻虫胺、吡虫清、吡虫啉、噻虫嗪;锐劲特、乙虫清;abmamectin、甲氨基阿维菌素、艾克敌105;氟唑虫清;二唑虫、氰氟虫胺;式Γ4的邻氨基苯甲酰胺化合物,JP 2002 284608、WO 02/89579、WO 02/90320、WO 02/90321、WO 04/06677、WO 04/20399、JP 2004 99597、WO 05/68423、WO 05/68432或WO 05/63694中所述的丙二腈化合物,尤其是丙二腈化合物CF2HCF2CF2CF2CH2C(CN)2CH2CH2CF3(2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(3,3,3-三氟丙基)丙二腈)、CF3(CH2)2C(CN)2CH2(CF2)5CF2H(2-(2,2,3,3,4,4,5,5,6,6,7,7-十二氟庚基)-2-(3,3,3-三氟丙基)丙二腈)、CF3(CH2)2C(CN)2(CH2)2C(CF3)2F(2-(3,4,4,4-四氟-3-三氟甲基丁基)-2-(3,3,3-三氟丙基)丙二腈)、CF3(CH2)2C(CN)2(CH2)2(CF2)3CF3(2-(3,3,4,4,5,5,6,6,6-九氟己基)-2-(3,3,3-三氟丙基)丙二腈)、CF2H(CF2)3CH2C(CN)2CH2(CF2)3CF2H(2,2-二(2,2,3,3,4,4,5,5-八氟戊基)丙二腈)、CF3(CH2)2C(CN)2CH2(CF2)3CF3(2-(2,2,3,3,4,4,5,5,5-九氟戊基)-2-(3,3,3-三氟丙基)丙二腈)、CF3(CF2)2CH2C(CN)2CH2(CF2)3CF2H(2-(2,2,3,3,4,4,4-七氟丁基)-2-(2,2,3,3,4,4,5,5-八氟戊基)丙二腈)和CF3CF2CH2C(CN)2CH2(CF2)3CF2H(2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(2,2,3,3,3-五氟丙基)丙二腈),pymetrazine,啶虫丙醚。
尤其优选式I化合物:1-(2,6-二氯-4-三氟甲基苯基)-3-(1-甲基-2,2-二氯环丙基)-5-甲基-1,2,4-三唑与A-1组农药之一的协同增效混合物。
还尤其优选式I化合物:1-(2,6-二氯-4-三氟甲基苯基)-3-(2,2-二氯环丙基)-5-甲基-1,2,4-三唑与A-1组农药之一的协同增效混合物。
协同增效混合物有利地降低了剂量率和/或增强了活性谱和/或使快速活性与延长的防治和/或耐药性管理相结合。与使用单一化合物可能获得的防治率相比,它们增强了对害虫的防治。
化合物I和II的混合物或者同时,即联合或分开,或依次使用的化合物I和II对上述目的害虫显示出显著的作用,在分开施用的情况下,施用顺序通常对防治措施的结果没有任何影响。
化合物I和化合物II通常以100∶1-1∶100,优选20∶1-1∶50,尤其是5∶1-1∶20的重量比施用。
本发明的协同增效混合物可以如下对式I化合物所述转化成常规配制剂。施用率的范围也如对式I化合物所述。
可以通过使目标寄生虫/害虫、其食物供应源、栖息地、繁殖地或其场所与杀虫有效量的式I化合物或组合物接触而防治昆虫。
“场所”是指其中害虫或寄生虫生长或可能生长的栖息地、繁殖地、植物、种子、土壤、区域、材料或环境。
“杀虫有效量”通常指对生长获得可观察到的效果所需要活性成分的量,所述效果包括坏死、死亡、阻滞、预防和去除效果,破坏效果或减少目标生物体的出现和活动的效果。对于在本发明中使用的各种化合物/组合物,杀虫有效量可以变化。组合物的杀虫有效量也会根据主要条件如所需杀虫效果及持续时间、天气、目标物种、场所、施用方式等而变化。
式I化合物及其组合物可用于保护木质材料,例如树木、护栏、枕木等,以及建筑物如房子、附属建筑物、工厂,还有建筑材料、家具、皮革、纤维、聚氯乙烯制品、电线和电缆等以防蚂蚁和/或白蚁,并防止蚂蚁和白蚁损害作物或人类(例如当害虫侵入房子和公共设施时)。式I化合物不仅施用于周围的土壤表面或地板下的土壤中以保护木质材料,而且还可以施用于堆积制品如地板下混凝土、亭柱、梁、胶合板、家具等的表面,木质制品如碎料板、半包板(half boards)等以及聚氯乙烯制品如包覆的电线、聚氯乙烯片材,绝热材料如聚苯乙烯泡沫等。在防止蚂蚁损害作物或人类的施用中,将本发明的蚂蚁防治组合物直接施用于蚂蚁等的巢穴或其周围环境或经由诱饵接触而施用。
本发明化合物或组合物还可以预防性地施用于预期出现害虫的地方。
式I化合物还可以通过使生长的植物与杀虫有效量的式I化合物接触而用于保护植物以免被害虫侵袭或侵染。这里的“接触”包括直接接触(将化合物/组合物直接施用于害虫和/或植物上,通常施用于植物的叶、茎或根上)和间接接触(将化合物/组合物施用于害虫和/或植物所在场所)。
在土壤处理或施用于害虫栖息地或巢穴的情况下,活性成分的施用量为0.0001-500g/100m2,优选0.001-20g/100m2。白蚁(等翅目)的土壤处理为本发明尤其优选的实施方案。
在材料保护中的常见施用率例如为0.01-1000g活性化合物/m2被处理材料,理想的是0.1-50g/m2。
用于浸渍材料的杀虫组合物通常含有0.001-95重量%,优选0.1-45重量%,更优选1-25重量%至少一种驱避剂和/或杀虫剂。
对于在诱饵组合物中的应用,活性成分的典型含量为0.0001-15重量%,理想的是0.001-5重量%活性化合物。所用组合物还可以包含其他添加剂如活性物质的溶剂、调味剂、防腐剂、染料或苦味剂。其吸引力还可以通过特殊颜色、形状或结构而增强。
对于在喷雾组合物中的应用,活性成分的含量为0.001-80重量%,优选0.01-50重量%,最优选0.01-15重量%。
对于在处理作物植株中的应用,本发明活性成分的施用率可以为0.1-4000g/公顷,理想的是25-600g/公顷,更理想的是50-500g/公顷。
式I化合物和包含它们的组合物还可以用于在包括温血动物(包括人)在内的动物和鱼中防治和预防侵袭和侵染。它们例如适于在哺乳动物如牛、绵羊、猪、骆驼、鹿、马、小猪、家禽、兔、山羊、狗和猫,水牛、驴、黇鹿和驯鹿,以及产皮动物如貂、灰鼠和浣熊,禽类如母鸡、鹅、火鸡和鸭以及鱼类如淡水鱼和咸水鱼如鲑鱼、鲤鱼和鳗鱼中防治和预防侵袭和侵染。
式I化合物以及包含它们的组合物优选用于在家养动物如狗或猫中防治和预防侵袭和侵染。
在温血动物和鱼类中的侵袭包括但不限于虱、叮咬虱、蜱、鼻蝇、羊蜱蝇(keds)、叮咬蝇、家蝇、蝇、蝇蛆幼虫、恙螨、蚋、蚊子和跳蚤。
式I化合物和包含它们的组合物适于内吸和/或非内吸防治体外和/或体内寄生虫。它们对所有或部分发育阶段有效。
式I化合物尤其可以用于防治体外寄生虫。
式I化合物尤其可以用于分别防治下列目和属的寄生虫:
蚤(蚤目),例如猫跳蚤、狗跳蚤、印鼠客蚤、致瘁蚤、穿皮潜蚤和具带病蚤,
蟑螂(蜚蠊目-Blattodea),例如德国小蠊、Blattella asahinae、美洲大蠊、日本大蠊、棕色蜚蠊、Periplaneta fuligginosa、澳洲蜚蠊和东方蜚蠊,蝇、蚊(双翅目),例如埃及伊蚊、白纹伊蚊、剌扰伊蚊、墨西哥果蝇、五斑按蚊、Anopheles crucians、白足按蚊、冈比亚按蚊、Anopheles freeborni、海南岛白踝按蚊、云南微小按蚊、四斑按蚊、红头丽蝇、蛆症金蝇、Chrysomya hominivorax、Chrysomya macellaria、鹿蝇、Chrysops silacea、Chrysops atlanticus、螺旋蝇、嗜人瘤蝇蛆、狂怒库蠓、尖音库蚊、斑蚊、致倦库蚊、媒斑蚊、Culiseta inornata、Culiseta melanura、Dermatobiahominis、小毛厕蝇、马蝇、刺舌蝇、须舌蝇、Glossina fuscipes、胶舌蝇、Haematobia irritans、Haplodiplosis equestris、潜蝇属、纹皮蝇、Leptoconops torrens、Lucilia caprina、铜绿蝇、丝光绿蝇、Lyeoriapectoralis、Mansonia属、家蝇、厩腐蝇、羊狂蝇、银足白蛉、Psorophoracolumbiae、Psorophora discolor、Prosimulium mixtum、赤尾麻蝇、肉蝇属、Simulium vittatum、厩螫蝇、牛虻、Tabanus atratus、红色原虻和Tabanus similis,
虱(毛虱目),例如人头虱、人体虱、阴虱、牛血虱、猪血虱、牛颚虱、Bovicolabovis、鸡虱、Menacanthus stramineus和Solenopotes capillatus,蜱和寄生螨(寄螨目(Parasitiformes)):蜱(蜱目(Ixodida)),例如黑脚硬蜱、全环硬蜱、太平洋硬蜱、棕色犬壁虱(Rhiphicephalus sanguineus)、安氏革蜱、美洲大革蜱、长星形壁虱、Ambryomma maculatum、Ornithodorushermsi、Ornithodorus turicata以及寄生螨(中气门目(Mesostigmata)),例如柏氏禽刺螨和鸡皮刺螨,辐螨亚目(Actinedida)(前气门亚目(Prostigmata))和粉螨亚目(Acaridida)(无气门亚目(Astigmata)),例如蜂盾螨属(Acarapis)、Cheyletiella spp.、Ornithocheyletia spp.、Myobia spp.、木虱属(Psorergatesspp.)、蠕形螨属(Demodex spp.)、恙螨属(Trombicula spp.)、Listrophorusspp.、粉螨属(Acarus spp.)、食酪螨属(Tyrophagus spp.)、嗜木螨属(Caloglyphus spp.)、Hypodectes spp.、Pterolichus spp.、瘁螨属(Psoroptesspp.)、足螨属(Chorioptes spp.)、耳瘁螨属(Otodectes spp.)、疥螨属(Sarcoptes spp.)、背肛螨属(Notoedres spp.)、脚螨属(Knemidocoptes spp.)、Cytodites spp.和Laminosioptes spp,臭虫(Heteropterida):温带臭虫、热带臭虫、Reduvius senilis、Triatomaspp.、Rhodnius ssp.、锥蝽属(Panstrongylus ssp.)和Arilus critatus,虱目(Anoplurida),例如血虱属(Haematopinus spp.)、颚虱属(Linognathusspp.)、人虱属(Pediculus spp.)、Phtirus spp.和管虱属(Solenopotes spp.),Mallophagida(亚目Arnblycerina和Ischnocerina),例如Trimenoponspp.、短角鸟虱属(Menopon spp.)、鸭虱属(Trinoton spp.)、Bovicola spp.、Werneckiella spp.、Lepikentron spp.、啮毛虱属(Trichodectes spp.)和猫毛虱属(Felicola spp.),
圆线虫:
Wipeworms和旋毛虫(Trichinosis)(毛管目(Trichosyringida)),例如毛形线虫科(Trichinellidae(旋毛线虫属(Trichinella spp.)(鞭虫科(Trichuridae))))、鞭虫属(Trichuris spp.)、毛细线虫属(Capillaria spp.),
小杆线虫目(Rhabditida),例如小杆线虫属(Rhabditis spp.)、类圆线虫属(Strongyloides spp.)、Helicephalobus spp.,
圆线虫目(Strongylida),例如圆线虫属(Strongylus spp.)、钩口线虫属(Ancylostoma spp.)、美洲板口线虫(Necator americanus)、仰口线虫属(Bunostomum spp.)(钩虫)、毛圆线虫属(Trichostrongylus spp.)、捻转血矛线虫(Haemonchus contortus.)、奥斯脱线虫属(Ostertagia spp.)、古柏线虫属(Cooperia spp.)、细颈线虫属(Nematodirus spp.)、网尾线虫属(Dictyocaulus spp.)、盅口线虫属(Cyathostoma spp.)、结节线虫属(Oesophagostomum spp.)、有齿肾线虫(Stephanurus dentatus)、盘头线虫属(Ollulanus spp.)、夏伯特线虫属(Chabertia spp.)、有齿肾线虫、气管比翼线虫(Syngamus trachea)、钩口线虫属、钩线虫属(Uncinaria spp.)、球头线虫属(Globocephalus spp.)、板口线虫属(Necator spp.)、后圆线虫属(Metastrongylus spp.)、毛细缪勒线虫(Muellerius capillaris)、原圆线虫属(Protostrongylus spp.)、管圆线虫属(Angiostrongylus spp.)、Parelaphostrongylus spp.、Aleurostrongylus abstrusus和肾膨结线虫(Dioctophyma renale),
肠圆线虫(蛔虫目(Ascaridida)),例如似蚓蛔线虫(Ascaris lumbricoides)、猪蛔虫(Ascaris suum)、鸡蛔虫(Ascaridia galli)、马副蛔虫(Parascarisequorum)、蠕形住肠线虫(Enterobius vermicularis(蛲虫))、犬弓首线虫(Toxocara canis)、狮弓蛔虫(Toxascaris leonine)、斯线虫属(Skrj abinemaspp.)和马尖尾线虫(Oxyuris equi),
驼形线虫目(Camallanida),例如Dracunculus medinensis(麦地那龙线虫),
旋尾线虫目(Spirurida),例如吸吮线虫属(Thelazia spp.)、吴策线虫属(Wuchereria spp.)、布鲁线虫属(Brugia spp.)、盘尾丝虫属(Onchocercaspp.)、恶丝虫属(Dirofilari spp.)、双瓣线虫属(Dipetalonema spp.)、腹腔丝虫属(Setaria spp.)、油脂线虫属(Elaeophora spp.)、狼旋尾线虫(Spirocercalupi)和胃线虫属(Habronema spp.),
棘头虫(棘头虫纲(Acanthocephala)),例如棘头虫属(Acanthocephalusspp.)、蛭形巨棘吻棘头虫(Macracanthorhynchus hirudinaceus)和钩居棘头虫属(Oncicola spp.),
涡虫(Plathelminthes):
吸虫(吸虫纲(Trematoda)),例如片形吸虫属(Fasciola spp.)、大拟片形吸虫(Fascioloides magna)、并殖吸虫属(Paragonimus spp.)、双腔吸虫属(Dicrocoelium spp.)、巴氏姜片吸虫(Fasciolopsis buski)、华枝睾吸虫(Clonorchis sinensis)、裂体吸虫属(Schistosoma spp.)、毛毕吸虫属(Trichobilharzia spp.)、似翼重翼吸虫(Alaria alata)、并殖吸虫属和Nanocyetes spp.,
Cercomeromorpha,尤其是绦虫纲(Cestoda(多节绦虫亚纲)),例如双叶槽绦虫属(Diphyllobothrium spp.)、Tenia spp.、棘球绦虫属(Echinococcusspp.)、犬复孔绦虫(Dipylidium caninum)、多头绦虫属(Multiceps spp.)、膜壳绦虫属(Hymenolepis spp.)、中带绦虫属(Mesocestoides spp.)、Vampirolepis spp.、莫尼茨绦虫属(Moniezia spp.)、裸头绦虫属(Anoplocephala spp.)、Sirometra spp.、裸头绦虫属和膜壳绦虫属。
式I化合物以及含有它们的组合物特别用于防治双翅目、蚤目和蜱目害虫,尤其用于防治蚊。
式I化合物以及含有它们的组合物在防治蝇中的用途是本发明的另一优选实施方案。
此外,尤其优选式I化合物以及含有它们的组合物在防治蚤类中的用途。
式I化合物以及含有它们的组合物在防治蜱中的用途为本发明的另一优选实施方案。
式I化合物还尤其可以用于防治体内寄生虫(圆线虫、棘头虫和涡虫)。
可以预防和治疗方式进行给药。
活性化合物的给药直接或以合适的制剂形式口服、局部/经皮或肠胃外进行。
对于温血动物的口服给药,可以将式I化合物配制成动物饲料、动物饲料预混物、动物饲料浓缩物、丸剂、溶液、糊、悬浮液、浸液、凝胶、片剂、大丸剂和胶囊。此外,式I化合物可以在其饮用水中给药于动物。对于口服给药,所选剂型应给动物提供0.01-100mg/kg动物体重/天,优选0.5-100mg/kg动物体重/天的式I化合物。
另外,式I化合物可以肠胃外给药于动物,例如通过腔内(intraruminal)、肌内、静脉内或皮下注射。式I化合物可以分散或溶于对于皮下注射而言生理上可接受的载体中。另外,可以将式I化合物配制成皮下给药用植入物。此外,式I化合物可以透皮给药于动物。对于肠胃外给药,所选剂型应给动物提供0.01-100mg/kg动物体重/天的式I化合物。
式I化合物还可以浸洗液、粉剂、粉末、项圈、挂牌(medallions)、喷雾剂、香波、蘸点(spot-on)和喷淋配制剂形式以及以软膏或水包油或油包水乳液局部给药于动物。对于局部施用,浸洗液和喷雾剂通常含有0.5-5,000ppm,优选1-3,000ppm式I化合物。此外,式I化合物可以配制成动物,特别是四足动物如牛和绵羊用耳贴。
合适的制剂是:
-溶液,如口服溶液、稀释后口服给药用浓缩物、用于皮肤上或用于体腔内的溶液、喷淋配制剂、凝胶;
-口服或皮肤给药乳液和悬浮液;半固体制剂;
-其中将活性化合物在软膏基质中或在水包油或油包水乳液基质中加工的配制剂;
-固体制剂如粉末、预混物或浓缩物、颗粒、丸剂、片剂、大丸剂、胶囊;
气雾剂和吸入剂,以及含有活性化合物的成型制品。
适于注射的组合物通过将活性成分溶于合适溶剂中并任选加入其他成分如酸、碱、缓冲盐、防腐剂和加溶剂而制备。过滤溶液并无菌填充。
合适的溶剂是生理上可耐受的溶剂如水,链烷醇如乙醇、丁醇、苄醇、甘油、丙二醇、聚乙二醇,N-甲基吡咯烷酮,2-吡咯烷酮及其混合物。
活性化合物可以任选溶于适于注射的生理上可耐受的植物油或合成油中。
合适的加溶剂是促进活性化合物在主溶剂中溶解或防止其沉淀的溶剂。实例是聚乙烯吡咯烷酮、聚乙烯醇、聚氧乙基化蓖麻油和聚氧乙基化脱水山梨糖醇酯。
合适的防腐剂是苄醇、三氯丁醇、对羟基苯甲酸酯和正丁醇。
口服溶液直接给药。浓缩物在预先稀释到使用浓度之后口服给药。口服溶液和浓缩物根据现有技术所述并如上面对注射溶液所述制备,杀菌程序并不是必需的。
将用于皮肤上的溶液滴上、散布、擦入、洒上或喷上。
用于皮肤上的溶液根据现有技术所述和上面对注射溶液所述制备,杀菌程序并不是必需的。
其他合适的溶剂是聚丙二醇,苯基乙醇,苯氧基乙醇,酯如乙酸乙酯或乙酸丁酯、苯甲酸苄基酯,醚如亚烷基二醇烷基醚,例如二丙二醇单甲醚,酮类如丙酮、甲基乙基酮,芳族烃类,植物和合成油,二甲基甲酰胺,二甲基乙酰胺,Transcutol,Solketal,碳酸亚丙酯及其混合物。
可能有利的是在制备过程中加入增稠剂。合适的增稠剂是无机增稠剂如膨润土、胶态硅酸、单硬脂酸铝,有机增稠剂如纤维素衍生物、聚乙烯醇及其共聚物、丙烯酸酯和甲基丙烯酸酯。
将凝胶施用于或散布于皮肤上或引入体腔中。凝胶通过用足以得到具有软膏状稠度的透明物质的增稠剂处理已经如在注射溶液情况下所述制备的溶液而制备。所用增稠剂是上面所给的增稠剂。
将喷淋配制剂喷淋或喷雾于皮肤的限定区域,活性化合物渗透皮肤并起内吸作用。
喷淋配制剂通过将活性化合物在合适的皮肤相容性溶剂或溶剂混合物中溶解、悬浮或乳化而制备。合适的话,加入其他助剂如着色剂、生物吸收促进物质、抗氧化剂、光稳定剂、粘合剂。
合适的溶剂是水,链烷醇,二醇,聚乙二醇,聚丙二醇,甘油,芳族醇如苄醇、苯乙醇、苯氧基乙醇,酯类如乙酸乙酯、乙酸丁酯、苯甲酸苄基酯,醚类如亚烷基二醇烷基醚如二丙二醇单甲醚、二甘醇单丁醚,酮类如丙酮、甲基乙基酮,环状碳酸酯如碳酸亚丙酯、碳酸亚乙酯,芳族和/或脂族烃类,植物或合成油,DMF,二甲基乙酰胺,正烷基吡咯烷酮如甲基吡咯烷酮、正丁基吡咯烷酮或正辛基吡咯烷酮,N-甲基吡咯烷酮,2-吡咯烷酮,2,2-二甲基-4-氧基-亚甲基-1,3-二氧戊环和甘油缩甲醛。
合适的着色剂是所有允许用于动物且可以溶解或悬浮的着色剂。
合适的吸收促进物质例如为DMSO,散布油如肉豆蔻酸异丙酯,壬酸二丙二醇酯,硅油及其与聚醚、脂肪酸酯、甘油三酯、脂肪醇的聚合物。
合适的抗氧化剂是亚硫酸盐或偏亚硫酸氢盐如偏亚硫酸氢钾、抗坏血酸、丁羟基甲苯、丁羟基茴香醚、生育酚。
合适的光稳定剂例如为novantisolic acid。
合适的粘合剂例如为纤维素衍生物,淀粉衍生物,聚丙烯酸酯,天然聚合物如藻酸盐、明胶。
乳液可以口服给药、皮肤给药或作为注射液给药。
乳液是油包水型或水包油型乳液。
它们通过将活性化合物溶于疏水相或亲水相中并借助合适的乳化剂和合适的话其他助剂如着色剂、吸收促进物质、防腐剂、抗氧化剂、光稳定剂、粘度提高物质用其他相的溶剂均化而制备。
合适的疏水相(油)是:
-液体石蜡,硅油,天然植物油如芝麻油、杏仁油、蓖麻油,合成甘油三酯如辛酸/癸酸甘油二酯,含链长为C8-C12的植物脂肪酸或其他精选天然脂肪酸的甘油三酯混合物,还可能含有羟基的饱和或不饱和脂肪酸的部分甘油酯混合物,C8-C10脂肪酸的甘油单酯和甘油二酯,
-脂肪酸酯如硬脂酸乙酯、己二酸二正丁基酯、月桂酸己酯、壬酸二丙二醇酯、中等链长的支化脂肪酸与链长为C16-C18的饱和脂肪醇的酯、肉豆蔻酸异丙酯、棕榈酸异丙酯、链长为C12-C18的饱和脂肪醇的辛酸/癸酸酯、硬脂酸异丙酯、油酸油基酯、油酸癸基酯、油酸乙酯、乳酸乙酯、蜡状脂肪酸酯如合成鸭尾骨腺脂肪、邻苯二甲酸二丁酯、己二酸二异丙酯以及与后者相关的酯混合物,
-脂肪醇如异十三烷醇、2-辛基十二烷醇、鲸蜡基硬脂醇、油醇,和
-脂肪酸如油酸,和
-其混合物。
合适的亲水相是水,醇类如丙二醇、甘油、山梨醇及其混合物。
合适的乳化剂是:
-非离子表面活性剂,例如聚乙氧基化蓖麻油、聚乙氧基化脱水山梨糖醇单油酸酯、脱水山梨醇单硬脂酸酯、甘油单硬脂酸酯、聚氧乙基硬脂酸酯、烷基酚聚乙二醇醚;
-两性表面活性剂如N-月桂基对亚氨基二丙酸二钠或卵磷脂;
-阴离子表面活性剂,如月桂基硫酸钠、脂肪醇醚硫酸盐、单/二烷基聚乙二醇醚正磷酸酯单乙醇铵盐;
-阳离子活性表面活性剂,如鲸蜡基三甲基氯化铵。
合适的其他助剂是提高粘度并稳定乳液的物质,如羧甲基纤维素、甲基纤维素和其他纤维素以及淀粉衍生物,聚丙烯酸盐、藻酸盐、明胶、阿拉伯胶、聚乙烯吡咯烷酮、聚乙烯醇、甲基乙烯基醚和马来酸酐的共聚物、聚乙二醇、蜡、胶态硅酸或上述物质的混合物。
悬浮液可以口服或局部/皮肤给药。它们通过将活性化合物悬浮于悬浮剂中而制备,合适的话加入其他助剂如润湿剂、着色剂、生物吸收促进物质、防腐剂、抗氧化剂、光稳定剂。
液体悬浮剂是所有均相溶剂和溶剂混合物。
合适的润湿剂(分散剂)是上面所给的乳化剂。
可以提到的其他助剂是上面所给的那些。
半固体制剂可以口服或局部/皮肤给药。它们与上述悬浮液和乳液的不同仅在于具有更高粘度。
为了生产固体制剂,将活性化合物与合适赋形剂混合,合适的话加入助剂,并制成所需形式。
合适的赋形剂是所有生理上耐受的固体惰性物质。所用的那些是无机和有机物质。无机物质例如为氯化钠,碳酸盐如碳酸钙,碳酸氢盐,氧化铝,钛氧化物,硅酸,泥质土(argillaceous earths),沉淀或胶态二氧化硅或磷酸盐。有机物质例如为糖、纤维素、食品和饲料如奶粉、动物粉、谷粉和碎片、淀粉。
合适的助剂是上面已经描述的防腐剂、抗氧化剂和/或着色剂。
其他合适的助剂是润滑剂和助流剂如硬脂酸镁、硬脂酸、滑石、膨润土,崩解促进物质如淀粉或交联聚乙烯吡咯烷酮,粘合剂如淀粉、明胶或线性聚乙烯吡咯烷酮以及干粘合剂如微晶纤维素。
可以用于本发明中的组合物通常可以包含约0.001-95%式I化合物。
通常有利的是以0.5-100mg/kg/天,优选1-50mg/kg/天的总量使用式I化合物。
即用制剂以10ppm至80重量%,优选0.1-65重量%,更优选1-50重量%,最优选5-40重量%的浓度含有防治寄生虫,优选体外寄生虫的化合物。
在使用之前稀释的制剂以0.5-90重量%,优选1-50重量%的浓度含有防治体外寄生虫的化合物。
此外,制剂以10ppm至2重量%,优选0.05-0.9重量%,非常特别优选0.005-0.25重量%的浓度包含防治体内寄生虫的式I化合物。
在本发明的优选实施方案中,包含式I化合物的组合物皮肤/局部施用。
在进一步优选的实施方案中,局部施用以含有化合物的成型制品如项圈、挂牌、耳贴、固定在身体部分上的绑带以及粘合条和箔的形式进行。
通常有利的是施用固体配制剂,其以10-300mg/kg,优选20-200mg/kg,最优选25-160mg/kg被处理动物体重的总量在三周内释放式I化合物。
为了制备成型制品,使用热塑性和柔性塑料以及弹性体和热塑性弹性体。合适的塑料和弹性体是与式I化合物充分相容的聚乙烯基树脂、聚氨酯、聚丙烯酸酯、环氧树脂、纤维素、纤维素衍生物、聚酰胺和聚酯。用于成型制品的塑料和弹性体以及制备程序的详细列举例如给于WO03/086075中。
活性化合物还可以与增效剂或防治病原性体内寄生虫和体外寄生虫的其他活性化合物的混合物使用。下列本发明化合物可以与其一起在温血动物和鱼类中用于防治和预防侵袭和侵染的农药用来阐述可能的组合,而不施以任何限制:
有机磷酸酯类:高灭磷、毒虫畏、二嗪农、敌敌畏、百治磷、乐果、乙硫磷、杀螟松、倍硫磷、异唑磷、马拉硫磷、稻丰散、伏杀磷、亚胺硫磷、辛硫磷、虫螨磷、丙溴磷、丙硫磷、乙丙硫磷、三唑磷、敌百虫、喹涕福(Quintiofos)、蝇毒磷(Coumaphos)、氯腈肟磷(Chlorphoxim)、乙基溴硫磷(Bromophos-ethyl)、2,3-对二氧杂环己烷二硫醇-S,S-二(O,O-二乙基二硫代膦酸酯(2,3-p-Dioxanedithiol-S,S-bis(O,O-diethylphosphorodithionat));
氨基甲酸酯类:棉铃威、丙硫克百威、甲萘威、丁硫克百威、双氧威、呋线威、二唑虫、唑蚜威;
合成除虫菊酯类:甲体氯氰菊酯、溴氰菊酯、醚菊酯、杀灭菊酯、(RS)氯氟氰菊酯、氯氟氰菊酯、氯菊酯、灭虫硅醚、氟胺氰菊酯、四溴菊酯、己体氯氰菊酯、氟氯苯菊酯(Flumethrin)、氟氯氰菊酯及其对映体和立体异构体、氯氰菊酯;
节肢动物生长调节剂:a)几丁质合成抑制剂:苯甲酰脲类:定虫隆、灭蝇胺(Cyromazine)、氟脲杀、氟螨脲、氟虫脲、氟铃脲、氟丙氧脲、双苯氟脲、伏虫隆、杀虫隆;噻嗪酮、茂醚、噻螨酮、特苯唑、四螨嗪;b)蜕皮激素拮抗剂:特丁苯酰肼、甲氧苯酰肼、双苯酰肼;c)保幼激素类似物:蚊蝇醚、蒙五一五、双氧威;d)类脂生物合成抑制剂:螺螨酯;(新)烟碱类:吡虫清、噻虫胺、氟啶虫酰胺、吡虫啉、硝胺烯啶、噻虫啉、噻虫嗪;
合成球虫病化合物,聚醚抗菌素:盐酸氨丙啉(Amprolium)、Robenidin、妥曲珠利(Toltrazuril)、莫能菌素(Monensin)、盐霉素(Salinomycin)、马杜霉素(Maduramicin)、拉沙里菌素(Lasalocid)、甲基盐霉素(Narasin)、生度米星(Semduramicin);
各种其它杀虫剂:齐墩螨素(Avermectins)、灭螨醌、虫螨脒(Amitraz)、艾扎丁、联苯肼酯、苏云金芽孢杆菌(Bacillus thuringiensis)、枯草芽孢杆菌(Bacillus subtilis)、杀螟丹、氟唑虫清、杀虫脒(Chlordimeform)、灭蝇胺、杀螨硫隆、呋虫胺(Dinetofuran)、茂醚、甲氨基阿维菌素、硫丹、依西太尔(Epsiprantel)、乙虫清、喹螨醚、锐劲特、伐虫脒(Formetanate)、伐虫脒盐酸盐(Formetanate hydrochloride)、灭蚁腙、二唑虫、氰氟虫胺、L-2,3,5,6-四氢-6-苯基咪唑并噻唑、左旋咪唑(Levamisole)、米尔螨素(Milbemectin)、莫昔克丁(Moxidectin)、吡喹酮(Praziquantel)、噻嘧啶(Pyrantel)、哒螨酮、拒嗪酮、赛拉菌素(Selamectin)、艾克敌105、硫、吡螨胺和硫环杀。
通常而言,“杀寄生虫有效量”指对生长获得可观察到的效果所需的活性成分量,所述效果包括坏死、死亡、阻滞、预防和除去效果,破坏效果或目标生物体的出现和活动降低效果。对于用于本发明的各种化合物/组合物,杀寄生虫有效量可以变化。组合物的杀寄生虫有效量也可以根据盛行的条件如所需杀寄生虫效果和持续时间、目标种类、施用方式等而改变。
合成实施例
根据下列合成实施例所示程序得到的化合物I与其物理数据一起列于下表I中。
实施例1
3-(2,2-二氯-1-甲基环丙基)-1-(2,6-二氯-4-三氟甲基苯基)-5-甲基-1H-[1,2,4]三唑的制备
将50g N-[1-(2,2,-二氯-1-甲基环丙基)亚乙基]-N’-(2,6-二氯-4-三氟甲基苯基)肼和17.9ml吡啶溶于1L甲苯中。在0-5℃下分批加入51g DDQ。在25℃下搅拌12小时后,加入1L 5%NaOH溶液,用醚萃取该混合物并用MgSO4干燥。除去溶剂得到48.6g上述化合物(熔点107-116℃)。
表I
序号 | X | Y | A | B | 物理数据(熔点[℃]/1H-NMR(CDCl3):d[ppm]) |
I-1 | Cl | CF3 | CH3 | H | 8.21(s),7.77(s),2.58(d),1.87(s),1.66(d) |
I-2 | Cl | CF3 | H | CH3 | 133-138 |
I-3 | Cl | CF3 | CH3 | CH3 | 107-116 |
EP 957 094的化合物
A | Cl | CF3 | H | H | 8.20(s),7.76(s),3.10(dd),2.34(t),2.09(dd) |
对害虫的作用实施例
试验方法
对害虫和寄生虫的作用实施例
1.经由玻璃接触对阿根廷蚁(Linepithema humile)、收获蚁(Pogonomyrmexcalifornicus)、飞行蚁(举腹蚁属)、木蚁(Camponotus floridanus)、红火蚁(Solenopsis invicta)、家蝇(Musca domestica)、厩螫蝇(Stomoxys calcitrans)、肉蝇(肉蝇属)、黄热病蚊(Aedes aegyptii)、家蚊(Culex quinquefasciatus)、疟蚊(Anopheles albimanus)、德国小蠊(Blattella germanica)、猫跳蚤(Ctenocephalides felis)和棕色犬壁虱(Rhipicephalus sanguineus)的活性
用0.5ml活性成分丙酮溶液处理玻璃小瓶并使其干燥。将昆虫或蜱与一些食物和水分供应源一起放入各小瓶中。将小瓶保持在22℃并在各时间间隔下观察处理效果。
在这些试验中,化合物I-3在0.1ppm的施用率下在处理后24小时显示出100%的黄热病蚊死亡率。
此外,化合物I-3在5ppm的施用率下在处理后24小时显示出100%的家蝇和德国小蠊死亡率。
此外,化合物I-3在10ppm的施用率下在处理后24小时显示出100%的举腹蚁属死亡率。
2.经由土壤接触对阿根廷蚁(Linepithema humile)、飞行蚁(举腹蚁属)、木蚁(Camponotus floridanus)、红火蚁(Solenopsis invicta)和黄肢散白蚁(Reticulitermes flavipes)的活性
对于蚂蚁,试验在陪替氏皿中进行。将1%琼脂水溶液的薄层分配到陪替氏皿中并在琼脂上铺上Florida砂质土。将活性成分溶于丙酮中并分配在砂土上。将各皿抽空以蒸发丙酮,用蚂蚁侵染并覆盖。将20%蜂蜜水溶液放入各皿中。将各皿维持在22℃下并在各个时间间隔下观察死亡率。
对于白蚁,将1%琼脂的薄层分配到陪替氏皿中。将预处理土壤的薄层铺在琼脂上。对于土壤处理,将活性成分以重量/重量基准稀释在丙酮中并掺入土壤中。将白蚁工蚁引入各皿中。滤纸用作食物源。将试验皿维持在约25℃。每天观察白蚁死亡率(死亡或不能直立且仅显示出微弱活动)。
在这些试验中,化合物I-3在1重量%的施用率下在处理后3天显示出100%的黄肢散白蚁死亡率。
此外,化合物I-3在10ppm的施用率下在处理后24小时显示出100%的木蚁死亡率。
3.经由诱饵对阿根廷蚁(Linepithema humile)、飞行蚁(举腹蚁属)、木蚁(Camponotus floridanus)、红火蚁(Solenopsis invicta)、家蝇(Muscadomestica)、黄肢散白蚁(Reticulitermes flavipes)、台湾乳白蚁(Coptotermesformosanus)和德国小蠊(Blattella germanica)的活性
对于阿根廷蚁、飞行蚁和木蚁,试验在陪替氏皿中进行。使用蜂蜜/水溶液或磨碎的猫粮制备诱饵。将活性成分的丙酮溶液加入诱饵中。将置于盖中的0.2ml已处理蜂蜜水溶液或150mg已处理猫粮加入各皿中。将各皿覆盖并维持在22℃的温度下。每天观察蚂蚁死亡率。
对于红火蚁,将玉米屑用作诱饵基质(0.1%活性成分)。将红火蚁成虫与诱饵一起置于陪替氏皿中。每天观察蚂蚁死亡率。
对于家蝇,使用出壳后2-5天的成虫进行诱饵试验。将活性成分的丙酮溶液施用于由奶粉和糖的混合物组成的诱饵基质中。将家蝇置于保持在约22℃的诱饵缸中并在处理后4小时观察快速活性(死亡加病态(不能直立))。
对于白蚁,将活性成分的丙酮溶液施用于滤纸上。活性成分百分数基于滤纸重量计算。每个试验陪替氏皿使用一张处理的滤纸和约30只白蚁工蚁进行生物分析。将试验皿维持在25℃并每天观察死亡率(死亡或垂死昆虫)或中毒。
对于蟑螂,将带有通风盖的盒子用作试验容器。使用磨碎的猫粮制备诱饵并基于重量/重量比掺入活性成分的丙酮溶液(每个盒子0.03g诱饵)。将各盒子维持在22℃并每天观察蟑螂死亡率。
在这些试验中,化合物I-3在0.005重量%的施用率下在处理后3天显示出100%的黄肢散白蚁死亡率。
4.经由水处理对黄热病蚊(Aedes aegyptii)、家蚊(Culex quinquefasciatus)和疟蚊(Anopheles albimanus)幼虫的活性
将孔板用作试验容器。将活性成分溶于丙酮中并用水稀释,得到所需浓度。将含有约1%丙酮的最终溶液放入各孔中。在各孔中加入约10只在1ml水中的蚊子幼虫(4龄幼虫)。幼虫每天进食一滴肝粉。将各皿覆盖并维持在22℃。每天记录死亡率并且每天取出死亡幼虫和活的或死的蛹。记录试验结束时剩下的活幼虫并计算死亡百分数。
5.对棉蚜(aphis gossypii)的活性
将活性化合物在50∶50丙酮∶水和100ppm KineticTM表面活性剂中配制。
通过将来自主群体的重度侵染叶子置于各子叶的顶部而将子叶阶段的棉花植物(每盆一株)侵染。使蚜虫在一夜内转移到宿主植株上并取走用于转移蚜虫的叶子。然后将子叶浸入试验溶液中并干燥。5天后进行死亡率计数。
在该试验中,化合物I-3在300ppm下显示出100%的死亡率。6.对桃蚜(Myzus persicae)的活性
将活性化合物在50∶50丙酮∶水和100ppm KineticTM表面活性剂中配制。
通过将侵染的叶片置于试验植物的顶部而将第2对叶阶段的辣椒植物(栽培品种为‘California Wonder’)用约40只实验室饲养的蚜虫侵染。24小时后移走所述叶片。将整个植物的叶子浸入试验化合物的梯度溶液中并进行干燥。在约25℃和20-40%相对湿度下将试验植物维持在荧光下(24小时光照)。5天后,相对于对照植物上的死亡率测定已处理植物上的蚜虫死亡率。
在该试验中,化合物I-3在300ppm下显示出100%的死亡率,而化合物A在300ppm下没有显示出效果。
7.对蚕豆蚜(Aphis fabae)的活性
将活性化合物在50∶50丙酮∶水和100ppm KineticTM表面活性剂中配制。
通过将侵染的切割植物置于试验植物的顶部而将生长在Metro混合物中的第一对叶阶段的旱金莲属植物(栽培品种为‘Mixed Jewel’)用约2-30只实验室饲养的蚜虫侵染。24小时后移走所述切割植物。将各植物浸入试验溶液中以完全覆盖叶、茎、伸出的种子表面和周围的立方表面并在通风橱中干燥。将已处理植物保持在约25℃和连续荧光下。3天后测定蚜虫死亡率。
在该试验中,化合物I-1和I-3在300ppm显示出100%的死亡率,而化合物A没有显示出效果。
8.对银叶粉虱(bemisia argentifolii)的活性
将活性化合物在50∶50丙酮∶水和100ppm KineticTM表面活性剂中配制。
使选取的棉花植物生长到子叶阶段(每盆一株)。将子叶浸入测试溶液中以完全覆盖叶面并放于良好通风的区域以进行干燥。将具有处理秧苗的各盆放入塑料杯中并引入10-12只银叶粉虱成虫(约3-5天龄)。使用呼吸器和连接于防渗移液管尖端的0.6cm无毒Tygon管(R-3603)收集昆虫。然后将含有收集的昆虫的该尖端轻轻地插入含有处理植物的土壤中,使昆虫爬出该尖端而到达叶面上取食。将杯子用可再用的筛盖(150微米网眼的聚酯筛PeCap,购自Tetko Inc)覆盖。将测试植物在保持室中于约25℃和20-40%相对湿度下保持3天,并避免直接暴露于荧光(24小时光照期)以防止在杯子内蓄积热。在处理植物3天后评价死亡率。
在该试验中,化合物I-1和I-3在300ppm下显示出100%的死亡率。9.对褐飞虱(nilaparvata lugens)的活性
将活性化合物在50∶50丙酮∶水中配制。将盆栽稻秧苗用10ml试验溶液喷雾,风干,置于笼中并用10只成虫接种。24、72和120小时后记录死亡百分数。
在该试验中,化合物I-1、I-2和I-3在300ppm下显示出100%的死亡率。
10.对豆蚜(Aphis craccivora)
将活性化合物在50∶50丙酮/水中配制。在记录害虫种群之后喷雾带有100-150只不同阶段的蚜虫的盆栽豇豆植物。24、72和120小时后记录种群减少。
在该试验中,化合物I-1、I-2和I-3在300ppm下显示出100%的死亡率,而化合物A没有显示出效果。
11.对菜蛾(plutella xylostella)的活性
将活性化合物在50∶50丙酮/水和0.1体积%Alkamuls EL 620表面活性剂中配制。将卷心菜叶子的6cm叶片浸入试验溶液中3秒并在衬有潮湿滤纸的陪替板中风干。将叶片用10只三龄幼虫接种并保持在25-27℃和50-60%湿度下3天。处理72小时后评价死亡率。
在该试验中,化合物I-1和I-3在300ppm下显示出100%的死亡率,而化合物A没有显示出效果。
12.式I化合物的协同增效混合物的杀虫作用
将用于科罗拉多马铃薯甲虫的土豆植物和用于烟青虫的两叶棉花植物用于生物分析。将切出植物叶浸入活性化合物的1∶1丙酮/水稀释液中。在干燥叶子之后,将它们单独放于陪替氏皿底部上的水润湿滤纸上。将各皿用5-7只幼虫侵染并用盖子覆盖。各处理稀释液重复4次。将试验皿维持在约27℃和60%湿度下。在处理后5天评价各皿中的存活和病态幼虫数并计算死亡百分数。
为了确定杀虫混合物是否协同增效,使用Limpel公式:
E=X+Y-XY/100
E=混合物的预期死亡%
X=单独测量的化合物X的死亡%
Y=单独测量的化合物Y的死亡%
若对混合物观察的死亡%大于预期的死亡%,则存在协同增效作用。
表1.化合物I-3与甲体氯氰菊酯的混合物的活性
活性成分 | 剂量率[ppm] | 科罗拉多马铃薯甲虫的死亡% | 烟青虫的死亡% | ||
I-3 | 300 | 71.4 | |||
100 | 12.5 | 0 | |||
甲体氯氰菊酯 | 0.06 | 17.5 | 7.2 | ||
0.03 | 0 | ||||
I-3+甲体氯氰菊酯 | 观察到的死亡% | 预计的死亡% | 观察到的死亡% | 预计的死亡% | |
300+0.06 | 92.9 | 73.5 | |||
300+0.03 | 82.1 | 71.4 | |||
100+0.06 | 79.2 | 27.8 | 82.1 | 7.2 | |
100+0.03 | 17.9 | 0 |
Claims (13)
2.根据权利要求1的式I化合物,其中B为甲基且X为氯。
3.根据权利要求1的式I化合物,其中A为甲基且X为氯。
4.1-(2,6-二氯-4-三氟甲基苯基)-3-(1-甲基-2,2-二氯环丙基)-5-甲基-1,2,4-三唑。
5.如权利要求1-4中任一项所定义的式I化合物在防治昆虫或螨虫中的用途。
6.一种通过使昆虫或螨虫或其食物供应源、栖息地或繁殖地与杀虫有效量的如权利要求1-4中任一项所定义的组合物或式I化合物接触而防治昆虫或螨虫的方法。
7.一种通过向生长的植物叶子或植物生长的土壤或水体施用杀虫有效量的如权利要求1-4中任一项所定义的组合物或式I化合物而保护生长的植物以防昆虫或螨虫侵袭或侵染的方法。
8.根据权利要求6或7的方法,其中昆虫或螨虫选自等翅目、双翅目、蜚蠊目(Blattodea)、膜翅目、蚤目和蜱螨目。
9.一种处理、防治、预防或保护动物以防寄生虫侵袭或侵染的方法,包括向动物口服、局部或胃肠外给予或施用杀寄生虫有效量的如权利要求1-4中任一项所定义的组合物或式I化合物或其对映体或可兽用盐。
10.一种制备用于处理、防治、预防或保护动物以防寄生虫侵袭或侵染的组合物的方法,该组合物包含杀寄生虫有效量的如权利要求1-4中任一项所定义的组合物或式I化合物或其对映体或可兽用盐。
11.如权利要求10所要求的方法,其中寄生虫选自双翅目、蚤目和蜱目。
12.包含杀虫或杀寄生虫有效量的如权利要求1-4中任一项所定义的组合物或式I化合物和可农用或可兽用载体的组合物。
13.协同增效混合物,包含协同增效有效量的式I化合物和其他农药。
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UY29578A1 (es) | 2007-01-31 |
TW200718690A (en) | 2007-05-16 |
EP1893020A1 (en) | 2008-03-05 |
PE20070053A1 (es) | 2007-02-06 |
JP2008545733A (ja) | 2008-12-18 |
IL187362A0 (en) | 2008-04-13 |
ZA200800026B (en) | 2009-08-26 |
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