CN116621727A - 一种芳基或杂芳基取代的间二酰胺类化合物或其作为农药可接受的盐、组合物及其用途 - Google Patents
一种芳基或杂芳基取代的间二酰胺类化合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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- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
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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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- A—HUMAN NECESSITIES
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- A01P7/00—Arthropodicides
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- A—HUMAN NECESSITIES
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- A01P7/00—Arthropodicides
- A01P7/04—Insecticides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D213/82—Amides; Imides in position 3
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- 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
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- General Health & Medical Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Insects & Arthropods (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明属于农药领域,具体涉及一种芳基或杂芳基取代的间二酰胺类化合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,具体涉及一种间二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
双酰胺类杀虫剂是继新烟碱类杀虫剂之后,最受市场关注的一类杀虫产品,也是近年增长最快的一类杀虫产品。昆虫的神经-肌肉、生长发育、呼吸和中肠是杀虫剂研发的主要生理学靶标。作为神经肌肉突触间信号传递的重要方式之一,配体门控离子通道(LGIC)在脊椎动物和无脊椎动物体内广泛存在,并对其维持神经系统的正常生理功能和生存起重要作用。破坏LGIC开启或关闭的正常状态,可使靶标昆虫出现快速的肌肉痉挛、行动失调和麻痹瘫痪等症状,停止进食直至死亡。双酰胺类杀虫剂尤其是邻苯二甲酰胺类化合物是公认的作用机理为破坏LGIC的主流产品,但由于其抗性问题逐渐出现、目前其推广和应用受到了阻碍;随后间二酰胺类化合物逐渐成为双酰胺类杀虫剂中的新秀。虽然目前市面上的间二酰胺类化合物能在一定程度上克服双酰胺类化合物的抗性问题,但随着现实中对杀虫剂的使用要求不断提高,开发更高效的杀虫剂仍是亟待解决的问题。
技术问题
为解决现有技术中存在的上述问题,本发明提供了一种芳基或杂芳基取代的间二酰胺类化合物或其作为农药可接受的盐、组合物及其用途,在农业害虫尤其是鳞翅目害虫的防治方面有优秀的持效性和速效性,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:一种芳基或杂芳基取代的间二酰胺类化合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、R3分别独立地选自H、卤素、CN、C1-C6烷基、卤代C1-C6烷基或C3-C6环烷基;
R4为C1-C6亚烷基;
R5选自H、C1-C6烷基、C3-C6环烷基、卤代C1-C6烷基、CN取代的C1-C6烷基或C3-C6环烷基取代的C1-C6烷基;
R6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;
G1、G2分别独立地选自O或S;
X1、X2分别独立地选自H、F、CN或NO2,X1、X2不同时为H;
Q选自被取代基取代或未被取代基取代的芳基或杂芳基取代。
进一步地,式(I)中,R1、R2分别独立地选自H、卤素、CN、C1-C4烷基、卤代C1-C4烷基或C3-C6环烷基,R3为卤代C3-C6烷基;
进一步地,R1、R2分别独立地选自H、F、Cl、Br、CN、Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、CF3、CHF2、CH2F、CCl3、CHCl2、CH2Cl、环丙烷基、环丁烷基、环戊烷基或环己烷基,R3为卤代C3-C4烷基;
再进一步地,R1、R2分别独立地选自Br、I、CF3,R1、R2相同或不同,R3为七氟异丙基或九氟-2-丁基。
进一步地,式(I)中,R4选自-CH2-、-CH2CH2-或-CH2CH2CH2-;
R5选自H、Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、环丙烷基取代的甲基或环丙烷基取代的乙基;
进一步地,R5选自Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu或t-Bu。
进一步地,式(I)中,X1、X2分别独立地选自H、F或CN,X1、X2不同时为H。
进一步地,式(I)中,G1、G2均为O;或,G1为S、G2为O。
进一步地,式(I)中,Q选自被1-3个取代基取代或未被取代基取代的五元或六元的芳基或杂芳基;
进一步地,所述五元或六元的芳基或杂芳基为苯基、吡啶基、噻吩基、呋喃基、吡唑基、吡咯基或噻唑基;
进一步地,所述取代基选自F、Cl、Br、CN、Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、CF3、CHF2、CH2F、CCl3、CHCl2、CH2Cl、环丙烷基、环丁烷基、环戊烷基或环己烷基。
进一步地,式(I)为:
所述的作为农药可接受的盐可以为本发明的芳基或杂芳基取代的间二酰胺类化合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芳基或杂芳基取代的间二酰胺类化合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芳基或杂芳基取代的间二酰胺类化合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芳基或杂芳基取代的间二酰胺类化合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芳基或杂芳基取代的间二酰胺类化合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。
本发明的式I化合物可由如下方法制备,除另有注明外,反应式中各基团定义同上文。
进一步地,反应可以在常压或高压下进行,优选在大气压下进行,可根据常规方法进行后处理。
进一步地,II的合成方法示例如下:
进一步地,II-3的合成方法示例如下:
II-3的合成方法也可如下:
进一步地,III可以通过市售方式获得。
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(Gryllotalpagryllotalpa)、飞蝗(Locusta migratoria)、双纹黑蝗(Melanoplusbivittatus)、红足黑蝗(Melanoplusfemurrubrum)、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.,蠼蛸(革翅目(Dermaptera)),例如欧洲球螋(forficula auricularia),虱(毛虱目(Phthiraptera)),例如人头虱(Pediculushumanus capitis)、人体虱(Pediculus humanus corporis)、阴虱(Pthirus pubis)、牛血虱(Haematopinuseurysternus)、猪血虱(Haematopinus suis)、牛颚虱(Linognathusvituli)、Bovicolabovis、鸡虱(Menopon gallinae)、Menacanthus stramineus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、大麻、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:
通过对具有间二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上引入了烷氧基取代的烷基结构,从而得到了一系列更加高效、可用于农业或林业杀虫用的具有极佳活性的化合物,尤其在低剂量下具有速效且持久的杀虫活性。
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、具体的化合物物性数据如表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。
式I所示结构中,X1为F、X2为H,具体结构如表1-1所示:
表1-1式I化合物结构
式I所示结构中,X1为CN、X2为H,具体结构如表1-2所示:
表1-2式I化合物结构
式I所示结构中,X1为H、X2为F,具体结构如表1-3所示:
表1-3式I化合物结构
表2 1H 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
化合物I-15的制备:
(1)2-三氟甲基-4-七氟异丙基苯胺的制备:
将FeSO4·7H2O(19.46g,0.07mol)配置成的1mol/L水溶液,邻三氟甲基苯胺(32.20g,0.20mol),2-七氟碘代丙烷(76.96g,0.26mol),20mL浓硫酸依次加入400mL DMSO中。于室温搅拌下向其中缓慢滴加双氧水47mL,随后通过LC-MS监测反应进程。反应结束后,向反应液中加入200mL饱和食盐水与500mL乙酸乙酯,萃取后收集有机相,经干燥后进行硅胶柱层析分离(展开剂比例为石油醚:乙酸乙酯=50:1),得目标产物(41.59g,产率63.2%),产品是黄色油状液体。
(2)N-(2-三氟甲基-4-七氟异丙基苯基)-2-氟-3-硝基苯甲酰胺的制备:
将2-氟-3-硝基苯甲酸(18.50g,0.10mol)溶于200mL二氯甲烷中,向其中滴入4滴DMF,于0℃缓慢滴入草酰氯(15.24g,0.12mol),滴完转移至室温搅拌3h,通过LC-MS监测反应进程。反应结束后,将反应液脱溶。随后用20mL乙腈溶解待用。
取2-三氟甲基-4-七氟异丙基苯胺(32.90g,0.1mol)溶于200mL乙腈中,向其中加入KI(3.32g,0.02mol),于室温下搅拌。随后向该反应体系中缓慢滴加2-氟-3-硝基苯甲酰氯的乙腈溶液,滴完升温至85℃搅拌20h,通过LC-MS监测反应进程。反应结束后,进行硅胶柱层析分离(展开剂比例为石油醚:乙酸乙酯=5:1),得目标产物(38.04g,产率为76.7%),产品是黄色油状液体。
(3)N-(2-三氟甲基-4-七氟异丙基苯基)-2-氟-3-氨基苯甲酰胺的制备:
取N-(2-三氟甲基-4-七氟异丙基苯基)-2-氟-3-硝基苯甲酰胺(37.20g,0.075mol),溶于300mL乙腈。依次加入溴素(9.00g,0.056mol),氢氧化钠(3.30g,0.083mol),30mL水。然后于35℃加热。过程中滴入113mL次氯酸钠水溶液。避光反应1.5h。反应结束后脱溶,加入乙酸乙酯和水萃取,有机相干燥脱溶后,得到目标产物(40.90g,产率为95.0%),产品是淡黄色固体。
(4)N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-N-甲氧基甲基-2-氟-3-硝基苯甲酰胺的制备:
将氢化钠(5.60g,60%,0.14mol)混合于150mL超干四氢呋喃中,于0℃下搅拌。取N-(2-三氟甲基-4-七氟异丙基苯基)-2-氟-3-氨基苯甲酰胺(40.18g,0.07mol),溶于50mL超干四氢呋喃,滴入反应体系中,加完搅拌30min。取溴甲基甲醚(13.64g,0.11mol)溶于20mL超干四氢呋喃中,逐滴加入反应体系中,搅拌10分钟后将N,N-二异丙基乙胺(9.05g,0.07mol)滴入反应液中,室温搅拌3h。通过LC-MS监测反应进程。反应结束后,将反应体系慢慢滴入0℃的500mL水中。然后加入乙酸乙酯萃取,干燥有机相,进行硅胶柱层析分离(展开剂比例为石油醚:乙酸乙酯=5:1),得到目标产物(27.90g,产率64.5%),黄色固体。
(5)N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-N-甲氧基甲基-2-氟-3-氨基苯甲酰胺的制备
将N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-N-甲氧基甲基-2-氟-3-硝基苯甲酰胺(40.17g,0.065mol)混合于200mL乙酸乙酯中,加入催化量钯碳,于40℃搅拌24h。通过LC-MS监测反应进程。反应结束后,过滤反应液,将反应液脱溶后,得到目标产物(37.91g,产率99.2%),为黄色油状物。
(6)化合物I-15的制备:
将6-氟烟酸(9.17g,0.065mol)混合于100mL氯化亚砜中,于80℃加热3h,通过LC-MS监测反应进程。反应结束后,减压脱溶得到粗品,溶于50mL甲苯待用。
取N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-N-甲氧基甲基-2-氟-3-氨基苯甲酰胺(37.63g,0.064mol)溶于150mL甲苯,加入之前所得酰氯的甲苯溶液,于100℃加热5h。通过LC-MS监测反应进程。反应结束后,浓缩反应液,加入乙酸乙酯和水萃取,有机相干燥后进行硅胶柱层析分离(洗脱剂比例为石油醚:乙酸乙酯=4:1),得到目标产物(39.72g,产率87.3%),为黄色固体,1H NMR(400MHz,DMSO-d6)δ10.45(s,1H),8.69(d,J=2.2Hz,1H),8.49(d,J=2.2Hz,1H),8.04–8.01(m,1H),7.87–7.80(m,2H),7.48–7.40(m,2H),6.88(t,J=8.0Hz,1H),4.86(s,2H),3.07(s,3H)。
实施例2
化合物I-39的制备:
(1)N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-N-乙氧基甲基-2-氟-3-硝基苯甲酰胺的制备:
将氢化钠(4.80g,60%,0.12mol)混合于150mL超干四氢呋喃中,于0℃下搅拌。取N-(2-三氟甲基-4-七氟异丙基苯基)-2-氟-3-氨基苯甲酰胺(34.44g,0.06mol),溶于50mL超干四氢呋喃,滴入反应体系中,加完搅拌30min。取溴甲基乙醚(15.18g,0.11mol)溶于20mL超干四氢呋喃中,逐滴加入反应体系中,搅拌10分钟后将N,N-二异丙基乙胺(7.76g,0.06mol)滴入反应液中,室温搅拌3h。通过LC-MS监测反应进程。反应结束后,将反应体系慢慢滴入0℃的500mL水中。然后加入乙酸乙酯萃取,干燥有机相,进行硅胶柱层析分离(展开剂比例为石油醚:乙酸乙酯=5:1),得到目标产物(22.79g,产率60.1%),黄色固体。
(2)N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-N-乙氧基甲基-2-氟-3-氨基苯甲酰胺的制备:
将N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-N-乙氧基甲基-2-氟-3-硝基苯甲酰胺(18.96g,0.03mol)混合于100mL乙酸乙酯中,加入催化量钯碳,于40℃搅拌24h。通过LC-MS监测反应进程。反应结束后,过滤反应液,将反应液脱溶后,得到目标产物(17.86g,产率98.9%),为黄色油状物。
(3)化合物I-39的制备:
将6-氟烟酸(9.17g,0.065mol)混合于100mL氯化亚砜中,于80℃加热3h,通过LC-MS监测反应进程。反应结束后,减压脱溶得到粗品,溶于50mL甲苯待用。
取N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-N-乙氧基甲基-2-氟-3-氨基苯甲酰胺(38.53g,0.064mol)溶于150mL甲苯,加入之前所得酰氯的甲苯溶液,于100℃加热5h。通过LC-MS监测反应进程。反应结束后,浓缩反应液,加入乙酸乙酯和水萃取,有机相干燥后进行硅胶柱层析分离(洗脱剂比例为石油醚:乙酸乙酯=4:1),得到目标产物(41.62g,产率89.7%),为黄色固体,1H NMR(400MHz,DMSO-d6)δ10.66(s,1H),8.69(d,J=2.2Hz,1H),8.50(d,J=2.1Hz,1H),8.05–8.03(m,1H),7.87–7.82(m,2H),7.50–7.48(m,1H),7.44(t,J=7.7Hz,1H),6.88(t,J=8.0Hz,1H),4.91(s,2H),3.30–3.22(m,2H),0.93(t,J=7.0Hz,3H).。
实施例3
化合物I-97的制备:
(1)2,6-二溴-4-七氟异丙基苯胺的制备:
将FeSO4·7H2O(19.46g,0.07mol)配置成的1mol/L水溶液,2,6,-二溴苯胺(50.20g,0.20mol),2-七氟碘代丙烷(76.96g,0.26mol),20mL浓硫酸依次加入400mL DMSO中。于室温搅拌下向其中缓慢滴加47mL双氧水,随后通过LC-MS监测反应进程。反应结束后,向反应液中加入200mL饱和食盐水与500mL乙酸乙酯,萃取后收集有机相,经干燥后进行硅胶柱层析分离(展开剂比例为石油醚:乙酸乙酯=50:1),得目标产物(65.03g,产率77.6%),产品是黄色油状液体。
(2)N-(2,6-二溴-4-七氟异丙基苯基)-2-氟-3-硝基苯甲酰胺的制备:
将2-氟-3-硝基苯甲酸(18.50g,0.10mol)溶于200mL二氯甲烷中,向其中滴入4滴DMF,于冰水浴下将草酰氯(15.24g,0.12mol)缓慢滴入,滴完转移至室温搅拌3h,通过LC-MS监测反应进程。反应结束后,将反应液脱溶。随后用20mL乙腈溶解待用。
取2,6-二溴-4-七氟异丙基苯胺(41.90g,0.1mol)溶于200mL乙腈中,向其中加入KI(3.32g,0.02mol),于室温下搅拌。随后向该反应体系中缓慢滴加2-氟-3-硝基苯甲酰氯的乙腈溶液,滴完升温至85℃搅拌20h,通过LC-MS监测反应进程。反应结束后,进行硅胶柱层析分离(展开剂比例为石油醚:乙酸乙酯=5:1),得目标产物(47.47g,产率为81.0%),产品是黄色油状液体。
(3)N-(2,6-二溴-4-七氟异丙基苯基)-N-甲氧基甲基-2-氟-3-硝基苯甲酰胺的制备:
将氢化钠(4.00g,60%,0.10mol)混合于100mL超干四氢呋喃中,于0℃下搅拌。取N-(2,6-二溴-4-七氟异丙基苯基)-2-氟-3-硝基苯甲酰胺(29.30g,0.05mol),溶于30mL超干四氢呋喃,滴入反应体系中,加完搅拌30min。取溴甲基甲醚(8.28g,0.06mol)溶于10mL超干四氢呋喃中,逐滴加入反应体系中,搅拌10分钟后将N,N-二异丙基乙胺(6.46g,0.05mol)滴入反应液中,室温搅拌3h。通过LC-MS监测反应进程。反应结束后,将反应体系慢慢滴入0℃的500mL水中。然后加入乙酸乙酯萃取,干燥有机相,进行硅胶柱层析分离(展开剂比例为石油醚:乙酸乙酯=5:1),得到目标产物(17.73g,产率56.3%),黄色固体。
(4)N-(2,6-二溴-4-七氟异丙基苯基)-N-甲氧基甲基-2-氟-3-氨基基苯甲酰胺的制备:
将N-(2,6-二溴-4-七氟异丙基苯基)-N-甲氧基甲基-2-氟-3-硝基苯甲酰胺(31.50g,0.05mol)混合于100mL乙酸乙酯中,加入催化量钯碳,于40℃搅拌24h。通过LC-MS监测反应进程。反应结束后,过滤反应液,将反应液脱溶后,得到目标产物(29.76g,产率99.2%),为黄色油状物。
(5)化合物I-97的制备:
将6-氟烟酸(7.47g,0.053mol)混合于100mL氯化亚砜中,于80℃加热3h,通过LC-MS监测反应进程。反应结束后,减压脱溶得到粗品,溶于50mL甲苯待用。
取N-(2,6-二溴-4-七氟异丙基苯基)-N-甲氧基甲基-2-氟-3-氨基基苯甲酰胺(31.20g,0.052mol)溶于150mL甲苯,加入之前所得酰氯的甲苯溶液,于100℃加热5h。通过LC-MS监测反应进程。反应结束后,浓缩反应液,加入乙酸乙酯和水萃取,有机相干燥后进行硅胶柱层析分离(洗脱剂比例为石油醚:乙酸乙酯=4:1),得到目标产物(32.35g,产率86.1%),为黄色固体。1H NMR(400MHz,DMSO-d6)δ10.52(s,1H),8.69(d,J=2.2Hz,1H),8.04–8.01(m,2H),7.87–7.80(m,2H),7.48–7.40(m,2H),6.88(t,J=8.0Hz,1H),4.96–4.94(m,1H),4.78–4.76(m,1H),3.07(s,3H).。
实施例4
化合物I-70的制备
(1)2-碘-4-七氟异丙基-6-三氟甲基苯胺的制备:
将2-三氟甲基-4-七氟异丙基苯胺(65.8g,0.20mol)溶于500mL乙醇中,于0℃下依次加入浓硫酸(23.93g,98.3%,0.24mol),N-碘代琥珀酰亚胺(56.25g,0.25mol)。加完移至室温搅拌1.5h后,升温至40℃搅拌4h。通过LC-MS监测反应进程。反应结束后,向反应液中加入4N NaOH水溶液至中和。然后加入乙酸乙酯和水萃取,有机相经干燥脱溶后获得产物(84.90g,产率77.8%),黄褐色油状物。
(2)N-(2-碘-4-七氟异丙基-6-三氟甲基苯基)-2-氟-3-硝基苯甲酰胺的制备:
将2-氟-3-硝基苯甲酸(18.50g,0.10mol)溶于200mL二氯甲烷中,向其中滴入4滴DMF,于冰水浴下将草酰氯(15.24g,0.12mol)缓慢滴入,滴完转移至室温搅拌3h,通过LC-MS监测反应进程。反应结束后,将反应液脱溶。随后用20mL乙腈溶解待用。
取2-碘-4-七氟异丙基-6-三氟甲基苯胺(45.50g,0.1mol)溶于200mL乙腈中,向其中加入KI(3.32g,0.02mol),于室温下搅拌。随后向该反应体系中缓慢滴加2-氟-3-硝基苯甲酰氯的乙腈溶液,滴完升温至85℃搅拌20h,通过LC-MS监测反应进程。反应结束后,进行硅胶柱层析分离(展开剂比例为石油醚:乙酸乙酯=5:1),得目标产物(52.56g,产率为84.5%),黄色固体。
(3)N-(2-碘-4-七氟异丙基-6-三氟甲基苯基)-N-甲氧基甲基-2-氟-3-硝基基基苯甲酰胺的制备:
将氢化钠(3.20g,60%,0.08mol)混合于100mL超干四氢呋喃中,于0℃下搅拌。取N-(2-碘-4-七氟异丙基-6-三氟甲基苯基)-2-氟-3-硝基苯甲酰胺(24.88g,0.04mol),溶于30mL超干四氢呋喃,滴入反应体系中,加完搅拌30min。取溴甲基甲醚(6.20g,0.05mol)溶于10mL超干四氢呋喃中,逐滴加入反应体系中,搅拌10分钟后将N,N-二异丙基乙胺(5.17g,0.04mol)滴入反应液中,室温搅拌3h。通过LC-MS监测反应进程。反应结束后,将反应体系慢慢滴入0℃的500mL水中。然后加入乙酸乙酯萃取,干燥有机相,进行硅胶柱层析分离(展开剂比例为石油醚:乙酸乙酯=5:1),得到目标产物(16.49g,产率61.9%),黄色固体。
(4)N-(2-碘-4-七氟异丙基-6-三氟甲基苯基)-N-甲氧基甲基-2-氟-3-氨基基苯甲酰胺的制备:
将N-(2-碘-4-七氟异丙基-6-三氟甲基苯基)-N-甲氧基甲基-2-氟-3-硝基苯甲酰胺(39.96g,0.06mol)混合于150mL乙酸乙酯中,加入催化量钯碳,于40℃搅拌24h。通过LC-MS监测反应进程。反应结束后,过滤反应液,将反应液脱溶后,得到目标产物(37.93g,产率99.4%),黄褐色油状物。
(5)化合物I-70的制备:
将6-氟烟酸(7.90g,0.056mol)混合于100mL氯化亚砜中,于80℃加热3h,通过LC-MS监测反应进程。反应结束后,减压脱溶得到粗品,溶于50mL甲苯待用。
取N-(2-碘-4-七氟异丙基-6-三氟甲基苯基)-N-甲氧基甲基-2-氟-3-氨基基苯甲酰胺(34.98g,0.055mol)溶于150mL甲苯,加入之前所得酰氯的甲苯溶液,于100℃加热5h。通过LC-MS监测反应进程。反应结束后,浓缩反应液,加入乙酸乙酯和水萃取,有机相干燥后进行硅胶柱层析分离(洗脱剂比例为石油醚:乙酸乙酯=4:1),得到目标产物(37.03g,产率88.7%),为黄色固体,1H NMR(400MHz,DMSO-d6)δ10.44(s,1H),8.69(d,J=2.2Hz,1H),8.42(d,J=2.3Hz,1H),8.30(d,J=2.4Hz,1H),7.87–7.80(m,2H),7.48–7.40(m,2H),6.88(t,J=8.0Hz,1H),4.84(s,2H),3.07(s,3H)。
实施例5
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15-70%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5-40%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20-60%式(Ⅰ)化合物在加入2-10%分散剂和1-5%润湿剂、0.1-2%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50-80%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6
生物活性评价:小菜蛾(Plutella xylostella)
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。
室内生物测定采用浸叶法。选取健康大小均匀一致的小菜蛾3龄幼虫进行试验,将甘蓝叶片置于待测药液中10秒后取出,待其自然晾干后置于培养皿中,每个皿接入30头幼虫,每个浓度处理设4次重复,设不含药剂相同含量的溶剂处理作为空白对照。置于(25±1)℃,光周期为16h:8h(光照:黑暗)的人工气候室进行饲养。药后2天调查小菜蛾死虫数,计算死亡率(保留整数)。
对照化合物结构如下所示:
活性如下:
部分化合物,例如,编号如前所示的下述化合物在2ppm的施用率下至少具有80%的优良活性:1-13、15、17-28、31-35、37、39、41-55、57、59-62、65-70、72、74、76-78、80、82-83、85-90、92-94、96-97、99-101、103-104、106-111、113-115、117、119-121、123-125、127-129、131、133-135、137-140、142-143、146-150、152、154、156、157-158、164-167、170、171、174、176、178、180、188、190、193、198、200、201、204、206、208-210、212、241-216、218、220-221、223、225、227-228、230、232、234-235、237-239、241-242、244-247、249、251、254、255、257-258、262、265-269、271-275、277-282、289、291、293、295、302-304、312、314、316、318、326-328、331、336-339、342-344、346-350、354-356、358-359、361-363、365-366、368-370、373、374、376-378、380-381、383-385、387-388、390-392、394-401、405-408、410-414、417。
而在相同条件下,CK1-8在2ppm的施用率下表现出不超过60%的活性。
将以上化合物进行低浓度活性测定,结果如下:
实施例7
生物活性评价:甜菜夜蛾(Laphygma exigua)
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。
室内生物测定采用浸叶法。选取健康大小均匀一致的甜菜夜蛾3龄幼虫进行试验,将甘蓝叶片置于待测药液中10秒后取出,待其自然晾干后置于培养皿中,每个皿接入30头幼虫,每个浓度处理设4次重复,设不含药剂相同含量的溶剂处理作为空白对照。置于(25±1)℃,光周期为16h:8h(光照:黑暗)的人工气候室进行饲养。药后2天调查甜菜夜蛾死虫数,计算死亡率(保留整数)。
活性如下:
部分化合物,例如,编号如前所示的下述化合物在2ppm的施用率下至少具有80%的优良活性:1-4、6-7、9-11、13、15、18、20、25、27、31、35、37、39、41-42、44、49、50-51、54-55、57、59、61-62、65-67、70、72、74、76-78、80、82-83、85-90、92-94、96-97、99-101、103-104、106-111、113-115、118-121、123-125、127-129、131、133-135、137-140、142-143、146-150、152、154、156、157-158、164-167、170、171、174、176、178、180、188、190、193、198、200、201、204、206、208-210、213、241-216、218、220-221、223、225、227-228、230、232、234-235、237-239、241-242、244-247、249、252、254、255、257-258、262、265-269、271-275、277-282、289、291、293、295、302-304、312、314、316、318、326-328、331、336-339、342-344、346-350、354-356、358-359、361-363、365-366、368-370、373、374、376-378、380-381、383-385、387-388、390-392、394-401、405-408、410-414、417。
而在相同条件下,CK1-8在2ppm的施用率下表现出不超过50%的活性。
将以上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)
1.一种芳基或杂芳基取代的间二酰胺类化合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、R3分别独立地选自H、卤素、CN、C1-C6烷基、卤代C1-C6烷基或C3-C6环烷基;
R4为C1-C6亚烷基;
R5选自H、C1-C6烷基、C3-C6环烷基、卤代C1-C6烷基、CN取代的C1-C6烷基或C3-C6环烷基取代的C1-C6烷基;
R6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;
G1、G2分别独立地选自O或S;
X1、X2分别独立地选自H、F、CN或NO2,X1、X2不同时为H;
Q选自被取代基取代或未被取代基取代的芳基或杂芳基取代。
2.如权利要求1所述的一种芳基或杂芳基取代的间二酰胺类化合物或其作为农药可接受的盐,其特征在于,式(I)中,R1、R2分别独立地选自H、卤素、CN、C1-C4烷基、卤代C1-C4烷基或C3-C6环烷基,R3为卤代C3-C6烷基;
优选地,R1、R2分别独立地选自H、F、Cl、Br、CN、Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、CF3、CHF2、CH2F、CCl3、CHCl2、CH2Cl、环丙烷基、环丁烷基、环戊烷基或环己烷基,R3为卤代C3-C4烷基;
再优选地,R1、R2分别独立地选自Br、I、CF3,R1、R2相同或不同,R3为七氟异丙基或九氟-2-丁基。
3.如权利要求1所述的一种芳基或杂芳基取代的间二酰胺类化合物或其作为农药可接受的盐,其特征在于,式(I)中,R4选自-CH2-、-CH2CH2-或-CH2CH2CH2-;
R5选自H、Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、环丙烷基取代的甲基或环丙烷基取代的乙基;
优选地,R5选自Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu或t-Bu。
4.如权利要求1所述的一种芳基或杂芳基取代的间二酰胺类化合物或其作为农药可接受的盐,其特征在于,式(I)中,X1、X2分别独立地选自H、F或CN,X1、X2不同时为H。
5.如权利要求1所述的一种芳基或杂芳基取代的间二酰胺类化合物或其作为农药可接受的盐,其特征在于,式(I)中,G1、G2均为O;或,G1为S、G2为O。
6.如权利要求1所述的一种芳基或杂芳基取代的间二酰胺类化合物或其作为农药可接受的盐,其特征在于,式(I)中,Q选自被1-3个取代基取代或未被取代基取代的五元或六元的芳基或杂芳基;
优选地,所述五元或六元的芳基或杂芳基为苯基、吡啶基、噻吩基、呋喃基、吡唑基、吡咯基或噻唑基;
优选地,所述取代基选自F、Cl、Br、CN、Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、CF3、CHF2、CH2F、CCl3、CHCl2、CH2Cl、环丙烷基、环丁烷基、环戊烷基或环己烷基。
7.如权利要求1所述的一种芳基或杂芳基取代的间二酰胺类化合物或其作为农药可接受的盐,其特征在于,式(I)为:
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任意一项所述的芳基或杂芳基取代的间二酰胺类化合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任一项所述的芳基或杂芳基取代的间二酰胺类化合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任一项所述的芳基或杂芳基取代的间二酰胺类化合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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