CN115894442A - 一种取代的苯酰胺类衍生物或其作为农药可接受的盐、组合物及其用途 - Google Patents
一种取代的苯酰胺类衍生物或其作为农药可接受的盐、组合物及其用途 Download PDFInfo
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- CN115894442A CN115894442A CN202211373522.7A CN202211373522A CN115894442A CN 115894442 A CN115894442 A CN 115894442A CN 202211373522 A CN202211373522 A CN 202211373522A CN 115894442 A CN115894442 A CN 115894442A
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- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明属于农药领域,具体涉及一种取代的苯酰胺类衍生物或其作为农药可接受的盐、组合物及其用途,所述化合物具有式(I)结构:
Description
技术领域
本发明属于农药技术领域,具体涉及一种取代的苯酰胺类化合物或其作为农药可接受的盐、组合物,并涉及这些化合物或其作为农药可接受的盐、组合物作为杀虫剂的用途。
背景技术
苯酰胺类化合物是一类杀虫活性良好的化合物,一直是新农药创制研究的优选方向;含氟衍生物,特别是含氟有机化合物,由于具有更好的脂溶性、稳定性和渗透性等特点,也同样是新农药创制研究的优选方向。2014年拜耳作物科学股份公司开发了第一个苯基吡唑烟酰胺类含氟杀虫剂,对鳞翅目、部分同翅目害虫具有很好的防效,自此引起了对该领域的研发热潮,其化学结构式如下所示:
但以上活性化合物仅对鳞翅目、部分同翅目等害虫具有较佳防效,而对于缨翅目、其它同翅目害虫的活性仍有较大的提升空间。因此为实现农药减量增效,亟需进一步拓宽苯基吡唑烟酰胺类杀虫剂的杀虫谱、提高其生物活性。
技术问题
为解决现有技术中存在的上述问题,本发明提供了一种取代的苯酰胺类衍生物或其作为农药可接受的盐、组合物及其用途,对鳞翅目、同翅目、缨翅目害虫有极佳生物活性,且不易与现有的双酰胺类化合物产生交互抗性。
技术解决方案
本发明为实现上述目的采用的技术方案是:一种取代的苯酰胺类衍生物或其作为农药可接受的盐,其结构式如式(I)所示:
式(I)中,R1、R2分别独立地选自H、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基取代的C1-C6烷基、C3-C6环烷基或C3-C6环烷基取代的C1-C6烷基;
R3选自H、卤素、CN、C1-C6烷基或卤代C1-C6烷基;
n为选自1-6的整数。
进一步地,式(I)中,R1选自H、C1-C6烷基、C3-C6环烷基或C3-C6环烷基取代的C1-C6烷基;
R2选自H、C1-C6烷基、卤代C1-C6烷基或C1-C6烷氧基取代的C1-C6烷基;
R3选自卤素、CN或卤代C1-C6烷基;
n为选自1-5的整数。
进一步地,式(I)中,R1为C1-C4烷基、C3-C6环烷基或C3-C6环烷基取代的C1-C6烷基;
R2为H或C1-C4烷基;
R3选自卤素或CN;
n为选自1-4的整数。
进一步地,式(I)中,R1为Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、环丙烷基、环丁烷基、环戊烷基、环己烷基或环丙烷基取代的甲基;
R2选自H、Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu或t-Bu;
R3选自F、Cl、Br或CN;
n为选自1-4的整数。
进一步地,式(I)中,式(I)中,R1选自甲基、乙基、正丙基、异丙基、环丙烷基或环丁烷基;
R2选自H、甲基或乙基;
R3选自F、Cl或Br;
n为1、2或3。
进一步地,式(I)中,R1选自甲基或环丙烷基;
R2选自H或甲基;
R3选自F、Cl或Br;
n为1、2或3。
进一步地,式(I)具体为:
所述的作为农药可接受的盐可以为本发明的取代的苯酰胺类衍生物与化学上可接受的酸进行反应制得的盐,其中化学上可接受的酸可以是无机酸(如盐酸、硫酸、磷酸或氢溴酸等)或有机酸(如草酸、马来酸、富马酸、苹果酸、酒石酸、柠檬酸或苯甲酸等);所述的农药可接受的盐也可以为本发明的取代的苯酰胺类衍生物与化学上可接受的碱进行反应制得的盐,其中化学上可接受的碱可以是无机碱(如氢氧化钠、氢氧化钾、氢氧化钙、碳酸钠、碳酸钾、碳酸氢钠或碳酸氢钾)或有机碱(如三甲胺、三乙胺等)。
进一步地,所述的作为农药可接受的盐可以为钾盐、钠盐、铵盐、钙盐、吡啶盐、胆碱盐、盐酸盐、磷酸盐、醋酸盐、苯磺酸盐或草酸盐。
本发明还公开了一种杀虫组合物,包括杀虫有效量的如上所述的取代的苯酰胺类衍生物或其作为农药可接受的盐中的至少一种;进一步地,还包括制剂载体或制剂助剂。
本发明还公开了一种防治植物害虫的方法,包括将杀虫有效量的如上所述的取代的苯酰胺类衍生物或其作为农药可接受的盐中的至少一种或如前所述的杀虫组合物使用在作物或害虫和/或其栖息地上。
本发明还公开了如上所述的取代的苯酰胺类衍生物或其作为农药可接受的盐中的至少一种或如前所述的杀虫组合物在农业和其它领域中控制植物害虫上的用途。
在上述化合物结构式的定义中,所使用的专业术语均具有如下含义:
卤或卤素:指氟、氯、溴、碘。
C1-C6烷基:碳原子数为1-6的直链或支链烷基,例如甲基、乙基、丙基、异丙基或正丁基、异丁基、仲丁基、叔丁基等。
卤代C1-C6烷基:碳原子数为1-6的直链或支链烷基,在这些烷基上的氢原子可部分或全部被卤素所取代,例如,氯甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基等。
式I所述化合物的合成方法,具体是将式Ⅺ化合物经由式Ⅹ、Ⅸ、VIII、VII、VI、V、IV、III、II化合物(在下列列举的化学式中,只要未另外进行定义,取代基和符号与式I中定义的取代基和符号具有相同的意义)制备得到式I化合物:
包含式(I)代表的化合物或其盐作为活性成分的杀虫剂,适用于控制果树、蔬菜、其它作物和观赏植物领域的土壤中的害虫。
能够应用本发明杀虫剂的害虫的例子包括、但不限于,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(Bupaluspiniarius)、Cacoecia murinana、Capuareticulana、Cheimatobia brumata、云杉色卷蛾(Choristoneura fumiferana)、Choristoneura occidentalis、二化螟(Cirphisunipuncta)、苹果小卷蛾(Cydiapomonella)、松毛虫(Dendrolimus pini)、Diaphanianitidalis、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(Grapholithafunebrana)、梨小食心虫(Grapholitha molesta)、棉铃虫(Heliothisarmigera)、烟芽夜蛾(Heliothis virescens)、玉米穗虫(Heliothis zea)、菜螟(Hellulaundalis)、Hiberniadefoliaria、美国白蛾(Hyphantria cunea)、苹果巢蛾(Hyponomeutamalinellus)、番茄虫蛾(Keiferia lycopersicella)、Lambdina fiscellaria、甜菜夜蛾(Laphygma exigua)、咖啡潜叶蛾(Leucoptera coffeella)、旋纹潜蛾(Leucopterascitella)、Lithocolletisblancardella、葡萄浆果小卷蛾(Lobesia botrana)、甜菜网螟(Loxostege sticticalis)、舞毒蛾(Lymantria dispar)、模毒蛾(Lymantria monacha)、桃潜蛾(Lyonetiaclerkella)、黄褐天幕毛虫(Malacosoma neustria)、甘蓝夜蛾(Mamestrabrassicae)、黄杉毒蛾(Orgyia pseudotsugata)、玉米螟(Ostrinia nubilalis)、小眼夜蛾(Panolisflammea)、棉花红铃虫(Pectinophora gossypiella)、疆夜蛾(Peridromasaucia)、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(Plathypenascabra)、菜蛾(Plutella xylostella)、大豆夜蛾(Pseudoplusiaincludens)、Rhyacioniafrustrana、Scrobipalpula absoluta、麦蛾(Sitotrogacerealella)、葡萄卷叶蛾(Sparganothis pilleriana)、草地夜蛾(Spodopterafrugiperda)、海灰翅夜蛾(Spodoptera littoralis)、斜纹夜蛾(Spodoptera litura)、Thaumatopoea pityocampa、绿色橡木飞蛾(Tortrix viridana)、粉纹夜蛾(Trichoplusiani)和Zeirapheracanadensi;
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)、Amphimallus solstitialis、Anisandrus dispar、墨西哥棉铃象(Anthonomus grandis)、苹花象(Anthonomuspomorum)、Aphthona euphoridae、Athous haemorrhoidalis、甜菜隐食甲(Atomarialinearis)、纵坑切梢小蠹(Blastophagus piniperda)、Blitophaga undata、蚕豆象(Bruchus rufimanus)、豌豆象(Bruchus pisorum)、欧洲兵豆象(Bruchus lentis)、苹卷象(Byctiscus betulae)、甜菜大龟甲(Cassida nebulosa)、Cerotoma trifurcata、金花金龟(Cetonia aurata)、白菜籽龟象(Ceuthorrhynchus assimilis)、芫菁龟象(Ceuthorrhynchus napi)、甜菜胫跳甲(Chaetocnema tibialis)、Conoderusvespertinus、石刁柏负泥虫(Crioceris asparagi)、Ctenicera ssp.、长角叶甲(Diabrotica longicornis)、Diabrotica semipunctata、Diabrotica 12-punctata、南美叶甲(Diabrotica speciosa)、玉米根叶甲(Diabroticavirgifera)、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(Ipstypographus)、烟草负泥虫(Lema bilineata)、黑角负泥虫(Lema melanopus)、马铃薯叶甲(Leptinotarsa decemlineata)、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(Oulemaoryzae)、葡萄黑耳喙象(Ortiorrhynchus sulcatus)、草莓根象甲(Otiorrhynchusovatus)、辣根猿叶甲(Phaedon cochleariae)、Phyllobius pyri、Phyllotretachrysocephala、食叶鳃金龟属(Phyllophaga sp.)、庭园发丽金龟(Phylloperthahorticola)、大豆淡足跳甲(Phyllotreta nemorum)、黄曲条菜跳甲(Phyllotretastriolata)、日本金龟子(Popillia japonica)、豌豆叶象(Sitonalineatus)和谷象(Sitophilus granaria);
蝇、蚊子(双翅目(Diptera)),例如埃及伊蚊(Aedes aegypti)、白纹伊蚊(Aedesalbopictus)、剌扰伊蚊(Aedes vexans)、苍墨西哥果蝇(Anastrepha ludens)、五斑按蚊(Anopheles maculipennis)、Anopheles crucians、白足按蚊(Anophelesalbimanus)、疟蚊(Anopheles gambiae)、Anopheles freeborni、白踝按蚊(Anophelesleucosphyrus)、微小按蚊(Anopheles minimus)、四斑按蚊(Anophelesquadrimaculatus)、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、Cochliomyiahominivorax、高粱瘿蚊(Contarinia sorghicola)、Cordylobia anthropophaga、Culicoides furens、尖音库蚊(Culex pipiens)、斑蚊(Culex nigripalpus)、致倦库蚊(Culex quinquefasciatus)、媒斑蚊(Culex tarsalis)、Culiseta inornata、Culisetamelanura、瓜蝇(Dacuscucurbitae)、油橄榄实蝇(Dacus oleae)、油菜叶瘿蚊(Dasineurabrassicae)、葱蝇(Delia antique)、麦地种蝇(Delia coarctata)、灰地种蝇(Deliaplatura)、甘蓝根蝇(Delia radicum)、人肤皮蝇(Dermatobia hominis)、小毛厕蝇(Fanniacanicularis)、Geomyza Tripunctata、马蝇(Gasterophilus intestinalis)、刺舌蝇(Glossinamorsitans)、须舌蝇(Glossina palpalis)、Glossina fuscipes、Glossinatachinoides、Haematobia irritans、Haplodiplosis equestris、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、Mansoniatitillanus、麦瘿蚊(Mayetiola destructor)、秋家蝇(Musca autumnalis)、家蝇(Muscadomestica)、厩腐蝇(Muscina stabulans)、羊狂蝇(Oestrus ovis)、Opomyzaflorum、欧洲麦秆蝇(Oscinella frit)、天仙子泉蝇(Pegomya hysocyami)、Phorbiaantiqua、萝卜蝇(Phorbia brassicae)、Phorbia coarctata、Phlebotomus argentipes、Psorophoracolumbiae、Psila rosae、Psorophora discolor、Prosimulium mixtum、樱桃实蝇(Rhagoletis cerasi)、苹果实蝇(Rhagoletis pomonella)、红尾肉蝇(Sarcophagahaemorrhoidalis)、肉蝇属(Sarcophaga)、Simulium vittatum、厩螫蝇(Stomoxyscalcitrans)、牛虻(Tabanus bovinus)、Tabanus atratus、红色原虻(Tabanuslineola)、Tabanus similis、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(Frankliniellaoccidentalis)、东方花蓟马(Frankliniella tritici)、桔梗蓟马(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、Heterotermes aureus、黄肢散白蚁(Reticulitermes flavipes)、南方散白蚁(Reticulitermes virginicus)、欧洲散白蚁(Reticulitermes lucifugus)、黑胸散白蚁(Reticulitermes santonensis)、Reticulitermes grassei、Termes natalensis和家白蚁蚁(Coptotermes formosanus);
蟑螂(蜚蠊目(Blattaria)-Blattodea),例如德国小蠊(Blattella germanica)、Blattella asahinae、美洲蟑螂(Periplaneta americana)、日本大蠊(Periplanetajaponica)、棕色蜚蠊(Periplaneta brunnea)、Periplaneta fuligginosa、澳洲蜚蠊(Periplaneta australasiae)和东方蜚蠊(Blatta orientalis);
臭虫、蚜虫、叶蝉、粉虱、介壳虫、蝉(半翅目(Hemiptera)),例如拟绿蝽(Acrosternum hilare)、玉米长蝽(Blissus leucopterus)、黑斑烟盲蝽(Cyrtopeltisnotatus)、棉红蝽(Dysdercus cingulatus)、Dysdercus intermedius、麦扁盾蝽(Eurygaster integriceps)、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(Lyguspratensis)、稻绿蝽(Nezara viridula)、甜菜拟网蝽(Piesma quadrata)、Solubeainsularis、Thyanta perditor、Acyrthosiphon onobrychis、落叶松球蚜(Adelgeslaricis)、Aphidula nasturtii、甜菜蚜(Aphis fabae)、草莓根蚜(Aphisforbesi)、苹果蚜(Aphis pomi)、棉蚜(Aphis gossypii)、北美茶簏子蚜(Aphisgrossulariae)、Aphisschneideri、卷叶蚜(Aphis spiraecola)、Aphis sambuci、豌豆蚜(Acyrthosiphonpisum)、马铃薯蚜(Aulacorthum solani)、银叶粉虱(Bemisiaargentifolii)、Brachycaudus cardui、杏圆尾蚜(Brachycaudus helichrysi)、Brachycaudus persicae、Brachycaudus prunicola、甘蓝蚜(Brevicoryne brassicae)、Capitophorus horni、Cerosipha gossypii、Chaetosiphon fragaefolii、Cryptomyzusribis、高加索冷杉椎球蚜(Dreyfusia nordmannianae)、云杉椎球蚜(Dreyfusia piceae)、居根西圆尾蚜(Dysaphis radicola)、Dysaulacorthum pseudosolani、Dysaphisplantaginea、Dysaphispyri、蚕豆微叶蝉(Empoasca fabae)、桃大尾蚜(Hyalopteruspruni)、Hyperomyzuslactucae、麦长管蚜(Macrosiphum avenae)、大戟长管蚜(Macrosiphum euphorbiae)、蔷薇管蚜(Macrosiphon rosae)、Megoura viciae、巢莱修尾蚜(Melanaphis pyrarius)、麦无网蚜(Metopolophium dirhodum)、Myzus persicae、冬葱瘤额蚜(Myzus ascalonicusDonc)、Myzuscerasi、李瘤蚜(Myzus varians)、Nasonoviaribis-nigri、稻飞虱(Nilaparvatalugens)、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(Rhopalosiphummaidis)、禾谷溢管蚜(Rhopalosiphum padi)、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)、Toxoptera aurantiiand、葡萄根瘤蚜(Viteusvitifolii)、Cimex lectularius、Cimex hemipterus、Reduviussenilis、Triatoma spp.和Arilus critatus;
蚂蚁、蜜蜂、黄蜂、叶蜂(膜翅目(Hymenoptera)),例如新疆菜叶蜂(Athaliarosae)、切叶蚁(Atta cephalotes)、Atta capiguara、Atta cephalotes、Attalaevigata、Atta robusta、Atta sexdens、Atta texana、举腹蚁属(Crematogaster)、Hoplocampaminuta、Hoplocampa testudinea、黑毛蚁(Lasius niger)、小黄家蚁(Monomoriumpharaonis)、热带火蚁(Solenopsis geminata)、红火蚁(Solenopsisinvicta)、黑火蚁(Solenopsis richteri)、南方火蚁(Solenopsis xyloni)、红蚂蚁(Pogonomyrmexbarbatus)、Pogonomyrmex californicus、大头蚁(Pheidolemegacephala)、天鹅绒蚂蚁(Dasymutilla occidentalis)、熊蜂属(Bombus)、大黄蜂(Vespula squamosa)、Paravespula vulgaris、Paravespula pennsylvanica、Paravespulagermanica、姬胡蜂(Dolichovespula maculata)、黄边胡蜂(Vespa crabro)、胡蜂(Polistes rubiginosa)、Campodontus floridanus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(Melanoplusbivittatus)、红足黑蝗(Melanoplus femurrubrum)、墨西哥黑蝗(Melanoplusmexicanus)、迁飞黑蝗(Melanoplus sanguinipes)、石栖黑蝗(Melanoplusspretus)、条纹红蝗(Nomadacris septemfasciata)、美洲沙漠蝗(Schistocercaamericana)、非洲沙漠蝗(Schistocerca gregaria)、摩洛哥戟纹蝗(Dociostaurusmaroccanus)、庭疾灶螽(Tachycines asynamorus)、塞内加尔小车蝗(Oedaleussenegalensis)、臭腹腺蝗(Zonozerus variegatus)、Hieroglyphus daganensis、Kraussaria angulifera、意大利蝗(Calliptamus italicus)、澳大利亚灾蝗(Chortoicetes terminifera)和褐飞蝗(Locustana pardalina);
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(Amblyomma americanum)、热带花蜱(Amblyomma variegatum)、Ambryomma maculatum、波斯锐缘蜱(Argas persicus)、牛壁虱(Boophilus annulatus)、Boophilus decoloratus、微小牛蜱(Boophilus microplus)、Dermacentor silvarum、安氏革螨(Dermacentor andersoni)、美洲大革螨(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(Ixodespacificus)、Ornithodorus moubata、Ornithodorus hermsi、Ornithodorusturicata、柏氏禽刺螨(Ornithonyssus bacoti)、Otobius megnini、鸡皮刺螨(Dermanyssusgallinae)、绵羊疥病(Psoroptes ovis)、棕色犬壁虱(Rhipicephalussanguineus)、Rhipicephalus appendiculatus、Rhipicephalus evertsi、人疥螨(Sarcoptes scabiei),以及瘿螨属(Eriophyidae),如苹果刺锈螨(Aculusschlechtendali)、Phyllocoptrataoleivora和Eriophyes sheldoni;细螨属(Tarsonemidae),如Phytonemus pallidus和侧多食跗线螨(Polyphagotarsonemuslatus);细须螨属(Tenuipalpidae),如紫红短须螨(Brevipalpus phoenicis);叶螨属(Tetranychidae),如朱砂叶螨(Tetranychuscinnabarinus)、神泽叶螨(Tetranychuskanzawai)、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(Panonychuscitri)和Oligonychus pratensis;蜘蛛目(Araneida),例如红斑寇蛛(Latrodectusmactans)和褐丝蛛(Loxosceles reclusa);
蚤(蚤目(Siphonaptera)),例如猫蚤(Ctenocephalides felis)、狗蚤(Ctenocephalides canis)、印鼠客蚤(Xenopsylla cheopis)、致痒蚤(Pulex irritans)、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 spp.,[0491]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(Pthiruspubis)、牛血虱(Haematopinuseurysternus)、猪血虱(Haematopinus suis)、牛颚虱(Linognathus vituli)、Bovicolabovis、鸡虱(Menopon gallinae)、Menacanthusstramineus和Solenopotes capillatus;
弹尾目(Collembola(跳虫)),例如棘跳虫属(Onychiurus)。
它们还适合防治线虫:植物寄生线虫如根结线虫,北方根结线虫(Meloidogynehapla)、南方根结线虫(Meloidogyne incognita)、爪哇根结线虫(Meloidogyne javanica)和其他根结线虫属(Meloidogyne);形成胞囊的线虫,马铃薯金线虫(Globoderarostochiensis)和其他球胞囊属(Globodera);禾谷胞囊线虫(Heteroderaavenae)、大豆胞囊线虫(Heterodera glycines)、甜菜胞囊线虫(Heterodera schachtii)、三叶草胞囊线虫(Heterodera trifolii)和其他胞囊线虫属(Heterodera);种子肿瘿线虫,粒线虫属(Anguina);茎叶线虫,滑刃线虫属(Aphelenchoides);刺线虫,杂草刺线虫(Belonolaimuslongicaudatus)和其他针刺线虫属(Belonolaimus);松线虫,松材线虫(Bursaphelenchusxylophilus)和其他伞滑刃线虫属(Bursaphelenchus);环形线虫,环纹线虫属(Criconema)、小环线虫属(Criconemella)、轮线虫属(Criconemoides)、中环线虫属(Mesocriconema);球茎线虫,腐烂茎线虫(Ditylenchus destructor)、甘薯茎线虫(Ditylenchus dipsaci)和其他茎线虫属(Ditylenchus);锥线虫,锥线虫属(Dolichodorus);螺旋形线虫,Heliocotylenchus multicinctus和其他Helicotylenchus属;鞘线虫和鞘形线虫,鞘线虫属(Hemicycliophora)和半轮线虫属(Hemicriconemoides);潜根线虫属(Hirshmanniella);冠线虫,枪线虫属(Hoplolaimus);伪根结线虫,珍珠线虫属(Nacobbus);针线虫,横带长针线虫(Longidorus elongatus)和其他长针线虫属(Longidorus);根腐线虫,Pratylenchus neglectus、穿刺根腐线虫(Pratylenchuspenetrans)、Pratylenchus curvitatus、全体短体线虫(Pratylenchusgoodeyi)和其他根腐线虫属(Pratylenchus);穿孔线虫,香蕉穿孔线虫(Radopholussimilis)和其他穿孔线虫属(Radopholus);肾形线虫,盘旋线虫(Rotylenchus robustus)和其他肾状线虫属(Rotylenchus);Scutellonema属;残根线虫,原始毛刺线虫(Trichodorus primitivus)和其他毛刺线虫属(Trichodorus);拟毛刺属(Paratrichodorus);阻长线虫,马齿苋矮化线虫(Tylenchorhynchus claytoni)、顺逆矮化线虫(Tylenchorhynchus dubius)和其他矮化线虫属(Tylenchorhynchus);柑桔线虫,半穿刺线虫属(Tylenchulus);剑线虫,剑线虫属(Xiphinema);以及其他植物寄生线虫。
它们还可用于防治蜘蛛(蜘蛛纲),如蜱螨(蜱螨目),例如软蜱科、硬蜱科和疥螨科,如长星形壁虱(Amblyomma americanum)、热带花蜱(Amblyomma variegatum)、波斯锐缘蜱(Argas persicus)、牛壁虱(Boophilus annulatus)、Boophilus decoloratus、微小牛蜱(Boophilus microplus)、Dermacentor silvarum、Hyalomma truncatum、蓖子硬蜱(Ixodesricinus)、Ixodes rubicundus、Ornithodorus moubata、Otobius megnini、鸡皮刺螨(Dermanyssus gallinae)、绵羊疥病(Psoroptes ovis)、Rhipicephalusappendiculatus、Rhipicephalus evertsi、人疥螨(Sarcoptes scabiei),以及瘿螨属(Eriophyidae),如苹果刺锈螨(Aculus schlechtendali)、Phyllocoptrata oleivora和Eriophyes sheldoni;细螨属(Tarsonemidae),如Phytonemus pallidus和侧多食跗线螨(Polyphagotarsonemuslatus);细须螨属(Tenuipalpidae),如紫红短须螨(Brevipalpusphoenicis);叶螨属(Tetranychidae),如朱砂叶螨(Tetranychus cinnabarinus)、神泽叶螨(Tetranychuskanzawai)、太平洋叶螨(Tetranychus pacificus)、棉叶螨(Tetranychustelarius)和二点叶螨(Tetranychus urticae),苹果叶螨(Panonychus ulmi)、柑椐叶螨(Panonychuscitri)和oligonychus pratensis。
本发明的杀虫剂所使用的植物对象没有特别地限定;可以提及例如,谷类(如,水稻、大麦、小麦、黑麦、燕麦、玉米、高粱等)、豆类(大豆、小豆、蚕豆、豌豆、落花生等)、果树/果实类(苹果、柑橘、梨、葡萄、桃、日本杏树、樱桃、胡桃、杏树、香蕉、草莓等)、蔬菜类(甘蓝、番茄、菠菜、椰菜、莴苣、洋葱、大葱、青椒等)、根菜类(胡萝卜、马铃薯、甘薯、萝卜、莲藕、芜箐等)、工业作物类(棉花、***、构树、结香花、油菜、甜菜、蛇麻草、甘蔗、糖用甜菜、橄榄、橡胶、咖啡、烟草、茶等)、浆果类(南瓜、黄瓜、西瓜、瓜等)、牧草类(果园草、蜀黍、梯牧草、苜蓿、紫花苜蓿等)、草坪草类(韩国结缕草、翦股颖等)、香料等用作物类(熏衣草、迷迭香、百里香、欧芹、胡椒、姜等)、以及花卉类(菊花、玫瑰、兰花等)。
有益效果
由于采用了上述技术方案,本发明的有益效果是:
通过对具有苯基吡唑烟酰胺结构的化合物进行化学修饰和分子设计,在酰胺基团的N上引入了氰基取代的结构,从而得到了一系列能广谱杀虫、可用于农业或林业杀虫用的具有极佳活性的化合物,尤其是对大部分同翅目害虫及缨翅目害虫具有出人意料的生物活性。
本发明的实施方式
下面将结合本发明实施例,对本发明实施例中的技术方案进行清楚、完整地描述。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
通过对所合成的化合物的经济性、多样性以及生物活性进行综合考量,优选了部分化合物列于下表中。具体的化合物结构如表1所示,具体的结构确证情况如表2所示。表1-2中的化合物只是为了更好的说明本发明,并不会对本发明产生限定,本领域的技术人员不应将此理解为本发明上述主题的范围仅限于以下化合物。
具体结构如表1所示:
表1式I化合物结构
序号 | <![CDATA[R<sub>1</sub>]]> | <![CDATA[R<sub>2</sub>]]> | <![CDATA[R<sub>3</sub>]]> | n | 序号 | <![CDATA[R<sub>1</sub>]]> | <![CDATA[R<sub>2</sub>]]> | <![CDATA[R<sub>3</sub>]]> | n |
1 | 环丙烷基 | H | Cl | 1 | 21 | 环丙烷基 | H | F | 1 |
2 | 环丙烷基 | H | Cl | 2 | 22 | 环丙烷基 | H | F | 2 |
3 | 环丙烷基 | Me | Cl | 1 | 23 | 环丙烷基 | Me | F | 1 |
4 | i-Pr | H | Cl | 1 | 24 | i-Pr | H | F | 1 |
5 | i-Pr | H | Cl | 2 | 25 | i-Pr | H | F | 2 |
6 | i-Pr | Me | Cl | 1 | 26 | i-Pr | Me | F | 1 |
7 | n-Pr | H | Cl | 1 | 27 | n-Pr | H | F | 1 |
8 | n-Pr | H | Cl | 2 | 28 | n-Pr | H | F | 2 |
9 | n-Pr | Me | Cl | 1 | 29 | n-Pr | Me | F | 1 |
10 | 环戊烷基 | H | Cl | 1 | 30 | 环戊烷基 | H | F | 1 |
11 | 环戊烷基 | H | Cl | 2 | 31 | 环戊烷基 | H | F | 2 |
12 | 环戊烷基 | Me | Cl | 1 | 32 | 环戊烷基 | Me | F | 1 |
13 | 环己烷基 | H | Cl | 1 | 33 | 环己烷基 | H | F | 1 |
14 | 环己烷基 | H | Cl | 2 | 34 | 环己烷基 | H | F | 2 |
15 | 环己烷基 | Me | Cl | 1 | 35 | 环丙烷基 | Me | F | 3 |
16 | MeO | OMeO | Cl | 0 | 36 | 环丙烷基 | Et | Cl | 2 |
17 | EtO | EtO | Cl | 0 | 37 | 环丙烷基 | Et | F | 2 |
18 | 环丙烷基 | 环丙烷基 | Cl | 0 | 38 | 环丙烷基 | H | Cl | 3 |
19 | 环丙烷基 | Me | Cl | 2 | 39 | 环丙烷基 | H | F | 3 |
20 | 环丙烷基 | Me | F | 2 | 40 | 环丙烷基 | Me | Cl | 3 |
表21H NMR数据
制备本发明化合物的方法在以下技术方案和实施例中进行了说明。原料可以经市场购买到或者可以通过文献中已知的方法或者如详解所示进行制备。本领域技术人员应当理解,也可以利用其它合成路线合成本发明的化合物。尽管在下文中已经对合成路线中的具体原料和条件进行了说明,但是,可以很容易地将其替换为其它类似的原料及条件,这些对本发明制备方法的变型或者变体而产生的诸如化合物的各种异构体等都包括在本发明范围内。另外,如下所述制备方法可以按照本发明公开内容、使用本领域技术人员熟知的常规化学方法进行进一步修饰。例如,在反应过程中对适当的基团进行保护等等。
实施例1
4-(七氟异丙烷)-基苯胺的合成:
向2L三口烧瓶中加入苯胺(46.55g、500mmol)、600ml甲基叔丁基醚、600ml水,机械搅拌条件下加入保险粉(109g、625mmol)、四丁基硫酸氢铵(8.5g、25mmol)、慢慢分批加入碳酸氢钠(88.5g、875mmol),慢慢滴加七氟异丙烷(185g、625mmol),室温搅拌过夜。TLC(PE/EA=50/1)检测反应完全停止反应,反应液分离收集有机相,剩余水相乙酸乙酯萃取,合并有机相,饱和食盐水洗涤三次,无水硫酸钠干燥,浓缩旋干得红棕色液体(115g,收率88%)。GC-MS[M]=261.2。
实施例2
2,6-二氯-4-(全氟丙烷-2-基)苯胺的合成:
冰水浴下,向1L单口瓶加入4-(七氟异丙烷)-基苯胺(26.1g、100mmol)、醋酸(500ml)、分批加入N-氯代丁二酰亚胺(NCS)(29.3g、220mmol),缓慢升至回流温度,搅拌数小时。TLC(PE/EA=50/1)检测反应完全停止反应,水洗,乙酸乙酯萃取,有机相饱和食盐水洗涤3次,无水硫酸钠干燥,减压蒸去溶剂,柱层析提纯得到棕红色针状结晶状产物(24.75g、收率75%)。GC-MS[M]=329.7。
实施例3
2,6-二氯-4-(全氟丙烷-2-基)苯肼的合成:
向500ml单口瓶加入2,6-二氯-4-(全氟丙烷-2-基)苯胺(16.45g、50mmol)、醋酸(20ml)、水(20ml)、硫酸(160ml)。升温至80℃,搅拌1小时。然后缓慢降至0℃,慢慢滴加亚硝酸钠(3.79g、55mmol)水溶液。滴加完毕,搅拌30分钟。将上述制好的重氮盐往氯化亚锡(22.56g、100mmol)的稀盐酸溶液中滴加,滴加完毕,将反应瓶转移至室温,搅拌2小时。抽滤,滤饼转入稀碱液中,乙酸乙酯萃取,饱和食盐水洗涤三次,无水硫酸钠干燥,浓缩旋干得红棕色固体(10.3g,收率60%)。LC-MS(ESI)[M+H]+=345.2,[M+Na]+=367.2。
实施例4
1-(2,6-二氯-4-(全氟丙烷-2-基)苯基)-1H-吡唑的合成:
向250ml单口瓶加入2,6-二氯-4-(全氟丙烷-2-基)苯肼(34.4g、100mmol)、乙醇(100ml)、硫酸(9.8g、100mmol)1,1,3,3-四甲氧基丙烷(18g、110mmol)。升温至80℃,搅拌3小时。TLC(PE/EA=50/1)检测反应完全停止反应,水洗,乙酸乙酯萃取,有机相饱和食盐水洗涤3次,无水硫酸钠干燥,减压蒸去溶剂,柱层析提纯得到棕红色油状产物(30.4g、收率80%)。LC-MS(ESI)[M+H]+=380.7,[M+Na]+=403.2。
实施例5
1-(2,6-二氯-4-(全氟丙烷-2-基)苯基)-4-碘-1H-吡唑的合成:
向500ml单口瓶加入1-(2,6-二氯-4-(全氟丙烷-2-基)苯基)-1H-吡唑(19g、50mmol)、乙腈(280ml)、NIS(45g、200mmol)。升温至回流温度,搅拌过夜。TLC(PE/EA=50/1)检测反应完全停止反应,水洗,乙酸乙酯萃取,有机相饱和食盐水洗涤3次,无水硫酸钠干燥,减压蒸馏省部分溶剂,抽滤,剩余有机相柱层析提纯得到白色固体产物(11.4g、收率45%)。LC-MS(ESI)[M+H]+=506.7,[M+Na]+=528.7。
实施例6
1-(2,6-二氯-4-(全氟丙烷-2-基)苯基)-4-(4,4,5,5-四甲基-1,3,2-二氧苯并呋喃-2-基)-1H-吡唑的合成:
向250ml单口瓶加入1-(2,6-二氯-4-(全氟丙烷-2-基)苯基)-4-碘-1H-吡唑(10g、20mmol)、DMSO(120ml)、联硼酸频那醇酯(6g、24mmol)、乙酸钾(3.9g、40mmol)、双三苯基磷二氯化钯(0.7g、1mmol)。将混合物用氮气吹1min。加热至80℃,搅拌8小时。TLC(PE/EA=50/1)检测反应完全停止反应,将反应混合物用乙酸乙酯稀释,通过硅藻土垫过滤,将滤液用饱和氯化铵水溶液和饱和食盐水洗涤3次。将有机相无水硫酸钠干燥,过滤浓缩旋干。所得棕色固体无须纯化直接用于下一步。
实施例7
2-氯-5-(1-(2,6-二氯-4-(全氟丙烷-2-基)苯基)-1H-吡唑-4-基)烟酸甲酯的合成:
向250ml单口瓶加入1-(2,6-二氯-4-(全氟丙烷-2-基)苯基)-4-(4,4,5,5-四甲基-1,3,2-二氧苯并呋喃-2-基)-1H-吡唑(10g、20mmol)、1,4-二氧六环(100ml)、水(20ml)、5-溴-2-氯烟酸甲酯(6g、24mmol)、碳酸钾(5.5g、40mmol)、双三苯基磷二氯化钯(0.7g、1mmol)。将混合物用氮气吹1min。加热至80℃,搅拌8小时。TLC(PE/EA=10/1)检测反应完全停止反应,将反应混合物用乙酸乙酯稀释,通过硅藻土垫过滤,将滤液用饱和氯化铵水溶液和饱和食盐水洗涤3次。将有机相无水硫酸钠干燥,过滤浓缩旋干。剩余有机相柱层析提纯得到淡黄色透明油状产物(4.4g、收率40%)。LC-MS(ESI)[M+H]+=549.8,[M+Na]+=571.7。
实施例8
2-氟-5-(1-(2,6-二氯-4-(全氟丙烷-2-基)苯基)-1H-吡唑-4-基)烟酸甲酯的合成:
向250ml单口瓶加入1-(2,6-二氯-4-(全氟丙烷-2-基)苯基)-4-(4,4,5,5-四甲基-1,3,2-二氧苯并呋喃-2-基)-1H-吡唑(10g、20mmol)、1,4-二氧六环(100ml)、水(20ml)、5-溴-2-氟烟酸甲酯(5.6g、24mmol)、碳酸钾(5.5g、40mmol)、双三苯基磷二氯化钯(0.7g、1mmol)。将混合物用氮气吹1min。加热至90℃,搅拌8小时。TLC(PE/EA=10/1)检测反应完全停止反应,将反应混合物用乙酸乙酯稀释,通过硅藻土垫过滤,将滤液用饱和氯化铵水溶液和饱和食盐水洗涤3次。将有机相无水硫酸钠干燥,过滤浓缩旋干。剩余有机相柱层析提纯得到淡黄色透明油状产物(3.8g、收率36%)。LC-MS(ESI)[M+H]+=533.8,[M+Na]+=555.9。
实施例9
2-氯-5-(1-(2,6-二氯-4-(全氟丙烷-2-基)苯基)-1H-吡唑-4-基)烟酸的合成:
向100ml单口瓶加入2-氯-5-(1-(2,6-二氯-4-(全氟丙烷-2-基)苯基)-1H-吡唑-4-基)烟酸甲酯(5.5g、10mmol)、氢氧化锂一水合物(0.84g、20mmol)、水(20ml)。将混合物40℃,搅拌4小时。TLC(PE/EA=5/1)检测反应完全停止反应,浓缩反应液,剩余物水洗,乙酸乙酯萃取,收集水相,用稀盐酸调节至Ph=4,析出固体,抽滤,烘干得白色固体产物(2.35g、收率44%)。LC-MS(ESI)[M+H]+=535.6,[M+Na]+=558.4。
实施例10
2-氯-5-(1-(2,6-二氯-4-(全氟丙烷-2-基)苯基)-1H-吡唑-4-基)烟碱酰氯的合成:
向100ml单口瓶加入2-氯-5-(1-(2,6-二氯-4-(全氟丙烷-2-基)苯基)-1H-吡唑-4-基)烟酸(535mg、1mmol)、草酰氯(151mg、1.2mmol)、二氯甲烷(10ml)、N,N-二甲基甲酰胺(10mg)。反应体系冒出大量气体,体系稳定后继续室温搅拌2小时。溶剂旋干,剩余物直接用于下一步。
实施例11
2-氯-N-(氰甲基)-N-环丙基-5-(1-(2,6-二氯-4-(全氟丙烷-2-基)苯基)-1H-吡唑-4-基)烟酰胺的合成:
室温下,向100ml单口瓶加入2-氯-5-(1-(2,6-二氯-4-(全氟丙烷-2-基)苯基)-1H-吡唑-4-基)烟碱酰氯(550mg、1mmol)、dipea(260mg、2mmol)、2-(环丙基氨基)乙腈(140mg、1.4mmol)、DCM(10ml)。搅拌2小时。TLC(PE/EA=3/1)检测反应完全停止反应,水洗,二氯甲烷萃取,收集有机相浓缩,剩余粗品柱层析得白色固体粉末反应液,剩余物水洗,乙酸乙酯萃取,收集水相,用稀盐酸调节至酸性,析出固体,抽滤,烘干得白色固体产物(275mg、收率45%)。LC-MS(ESI)[M+H]+=413.9,[M+Na]+=636.4。
实施例12
N-(氰基甲基)-5-(1-(2,6-二氯-4-(全氟丙烷-2-基)苯基)-1H-吡唑-4-基)-2-氟-N-异丙基烟酰胺的合成:
室温下,向100ml单口瓶加入5-(1-(2,6-二氯-4-(全氟丙烷-2-基)苯基)-1H-吡唑-4-基)-2-氟烟碱酰氯(535mg、1mmol)、dipea(260mg、2mmol)、2-(异丙基氨基)乙腈(130mg、1.3mmol)、DCM(10ml)。搅拌2小时。TLC(PE/EA=3/1)检测反应完全停止反应,水洗,二氯甲烷萃取,收集有机相浓缩,剩余粗品柱层析得白色固体粉末反应液,剩余物水洗,乙酸乙酯萃取,收集水相,用稀盐酸调节至酸性,析出固体,抽滤,烘干得白色固体产物(275mg、收率45%)。LC-MS(ESI)[M+H]+=600.2,[M+Na]+=622.1。
实施例13
制剂的制备:
1、可溶性液剂:将10-50%式(Ⅰ)化合物和5-20%润湿剂溶于加至100%的水和/或水溶性溶剂中得到产品。
2、乳油:将10-70%式(Ⅰ)化合物和5-10%乳化剂溶于加至100%的水不溶性有机溶剂中得到产品。
3、水乳剂:将5-30%式(Ⅰ)化合物和1-10%乳化剂溶于20-40%水不溶性有机溶剂中。借助乳化机将该混合物引入加至100%的水中并制成均相乳液得到产品。
4、悬浮剂:在搅拌的球磨机中将10-50%式(Ⅰ)化合物在加入2-10%分散剂和1-5%润湿剂、0.1-5%增稠剂和加至100%的水中粉碎,制成活性物质悬浮液得到产品。
5、水分散粒剂:在加入加至100%的分散剂和润湿剂下研磨10-70%式(Ⅰ)化合物并借助工业生产设备将其制成水分散粒剂得到产品。
以上均为重量百分比。
实施例14
生物活性评价:小菜蛾
将待测化合物用N,N-二甲基甲酰胺溶解后,用含有0.1%吐温-80的水稀释至所需的浓度。室内生物测定选用浸叶法。选取健康一致的小菜蛾3龄幼虫,用镊子将新鲜甘蓝叶片置于药液中浸渍10秒钟后取出,待药液自然晾干后将甘蓝叶片置于垫有保湿滤纸的培养皿中,每皿20头小菜蛾3龄幼虫,每个处理4次重复,以不含待测化合物溶剂的空白处理作为对照。处理后的试虫置于25±1℃,光照时间L:D=16h:8h,相对湿度为60%的人工智能培养室进行饲养。药后3天调查小菜蛾死虫数,计算死亡率(保留整数)。
活性如下:在2ppm浓度下,本申请化合物中防效大于90%的1-9、12、14-15、18-29、35-40。
将对照化合物与部分本发明化合物进行低浓度活性测定,结果如下:
实施例15
生物活性评价:花蓟马
将待测化合物用N,N-二甲基甲酰胺溶解后,用含有0.1%吐温-80的水稀释至所需的浓度。室内生物测定选用试管药膜法。采自温室内未使用任何农药的玉米植株上的花蓟马,选择健康活泼的个体进行试验。将各浓度药液分别注满1.5mL离心管,放置5h后倒掉药液、晾干待用;用打孔器将新鲜甘蓝叶片打成直径为1cm的圆片,将叶片分别在每个浓度药液中浸10s,取出置于吸水纸上晾干后,用镊子夹入相应浓度药液的离心管中,每管1片;每浓度重复3次,以不含待测化合物的溶剂浸管、浸叶的处理为空白对照;用吸虫器将供试花蓟马吸入离心管中,每重复20头。用200目纱网盖好管口后置于25±1℃,光照时间L:D=16h:8h,相对湿度为75±5%的人工智能培养室进行饲养。药后2天调查花蓟马死虫数,计算死亡率(保留整数)。
将对照化合物与部分本发明化合物进行低浓度活性测定,结果如下:
上述实施例只是为了说明本发明的技术构思及特点,其目的是在于让本领域内的普通技术人员能够了解本发明的内容并据以实施,并不能以此限制本发明的保护范围。凡是根据本发明内容的实质所作出的等效的变化或修饰,都应涵盖在本发明的保护范围内。
Claims (10)
2.如权利要求1所述的一种取代的苯酰胺类衍生物或其作为农药可接受的盐,其特征在于,式(I)中,R1选自H、C1-C6烷基、C3-C6环烷基或C3-C6环烷基取代的C1-C6烷基;
R2选自H、C1-C6烷基、卤代C1-C6烷基或C1-C6烷氧基取代的C1-C6烷基;
R3选自卤素、CN或卤代C1-C6烷基;
n为选自1-5的整数。
3.如权利要求1或2所述的一种取代的苯酰胺类衍生物或其作为农药可接受的盐,其特征在于,式(I)中,R1为C1-C4烷基、C3-C6环烷基或C3-C6环烷基取代的C1-C6烷基;
R2为H或C1-C4烷基;
R3选自卤素或CN;
n为选自1-4的整数。
4.如权利要求3所述的一种取代的苯酰胺类衍生物或其作为农药可接受的盐,其特征在于,式(I)中,R1为Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、环丙烷基、环丁烷基、环戊烷基、环己烷基或环丙烷基取代的甲基;
R2选自H、Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu或t-Bu;
R3选自F、Cl、Br或CN;
n为选自1-4的整数。
5.如权利要求1-4任一项所述的一种取代的苯酰胺类衍生物或其作为农药可接受的盐,其特征在于,式(I)中,式(I)中,R1选自甲基、乙基、正丙基、异丙基、环丙烷基或环丁烷基;
R2选自H、甲基或乙基;
R3选自F、Cl或Br;
n为1、2或3。
6.如权利要求1-5任一项所述的一种取代的苯酰胺类衍生物或其作为农药可接受的盐,其特征在于,式(I)中,R1选自甲基或环丙烷基;
R2选自H或甲基;
R3选自F、Cl或Br;
n为1、2或3。
8.一种杀虫组合物,其特征在于,包括杀虫有效量的权利要求1-7任一项所述的取代的苯酰胺类衍生物或其作为农药可接受的盐中的至少一种;优选的,还包括制剂载体或制剂助剂。
9.一种防治植物害虫的方法,其特征在于,包括将杀虫有效量的权利要求1-7任一项所述的取代的苯酰胺类衍生物或其作为农药可接受的盐中的至少一种或如权利要求8所述的杀虫组合物使用在作物或害虫和/或其栖息地上。
10.如权利要求1-7任一项所述的取代的苯酰胺类衍生物或其作为农药可接受的盐中的至少一种或如权利要求8所述的杀虫组合物在农业和其它领域中控制植物害虫上的用途。
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CN110049975A (zh) * | 2016-12-08 | 2019-07-23 | 拜耳作物科学股份公司 | 制备5-(1-苯基-1h-吡唑-4-基)烟酰胺衍生物及类似化合物而不分离或纯化苯肼中间体的方法 |
CN112334457A (zh) * | 2018-06-22 | 2021-02-05 | 拜耳公司 | 制备三环化合物的方法 |
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CN106103414A (zh) * | 2013-11-05 | 2016-11-09 | 拜耳作物科学股份公司 | 用于节肢动物处理的取代的苯酰胺类 |
CN110049975A (zh) * | 2016-12-08 | 2019-07-23 | 拜耳作物科学股份公司 | 制备5-(1-苯基-1h-吡唑-4-基)烟酰胺衍生物及类似化合物而不分离或纯化苯肼中间体的方法 |
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