CN100349901C - 邻氨基苯甲酰胺杀虫剂 - Google Patents
邻氨基苯甲酰胺杀虫剂 Download PDFInfo
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- CN100349901C CN100349901C CNB2003801008458A CN200380100845A CN100349901C CN 100349901 C CN100349901 C CN 100349901C CN B2003801008458 A CNB2003801008458 A CN B2003801008458A CN 200380100845 A CN200380100845 A CN 200380100845A CN 100349901 C CN100349901 C CN 100349901C
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
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- C07—ORGANIC CHEMISTRY
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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Abstract
本发明提供了通式(I)化合物,N-氧化物及其适合的盐,其中,A是O或S(O)m;J是此处所定义的苯基或杂环;R1至R12、n、m和r如说明书所定义。也公开了防治无脊椎害虫的方法,包括用生物有效量的通式I化合物、N-氧化物及化合物的适合的盐(例如此处所描述的组合物)接触无脊椎害虫或其环境。本发明也涉及防治无脊椎害虫的组合物,包含生物有效量的通式I化合物、N-氧化物或化合物的适合的盐,和至少一种另外的选自表面活性剂、固体稀释剂和液体稀释剂的组分。
Description
发明领域
本发明涉及某些杂环酰胺、它们的N-氧化物、盐和适于农业和非农业应用,包括下文所列用途的组合物,以及它们在农业和非农业环境中用于防治无脊椎害虫的方法。
发明背景
无脊椎害虫的防治在实现高效农业的过程中是非常重要的。无脊椎害虫对生长着和储存后的农作物的危害会导致严重减产,从而增加消费者的费用。无脊椎害虫的防治在森林、温室作物、观赏植物、苗圃作物、储存食品和纤维产品、家畜、家庭,以及公共卫生和动物保健中也是重要的。虽然可购得用于上述目的的许多产品,但是仍然需要更有效、低廉、低毒、对环境安全或具有不同作用方式的新化合物。
PCT公开文本WO 01/070671公开了用作杀节肢动物剂的式i的N-酰基邻氨基苯甲酸衍生物
其中,A和B尤其独立地是O或S;J是任选的取代的苯环、5或6元杂芳环、萘环系或芳香族8、9或10元稠合的杂二环环系;R1和R3独立地是H或任选的取代的C1-C6烷基;R2是H或C1-C6烷基;每个R4独立地是H、C1-C6烷基、C1-C6卤代烷基、卤素或CN;和n是1-4。
发明概述
本发明提供了通式I的化合物、其N-氧化物或农业上适合的盐,
其中
A是O或S(O)m;
J是苯基,任选地被1-4个独立地选自基团R15的取代基取代的苯基;或
J是选自以下基团的杂环
每个R1独立地选自C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C6环烷基、C1-C6卤代烷基、C2-C6卤代链烯基、C2-C6卤代炔基、C3-C6卤代环烷基、卤素、CN、NO2、羟基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、C2-C4烷氧基羰基、C2-C4烷氨基羰基、C3-C5二烷氨基羰基、C1-C4烷氨基、C1-C8二烷氨基、C3-C6环烷基氨基和C3-C6三烷基甲硅烷基;或
每个R1独立地选自苯基、苯甲基和苯氧基,每个基团任选地被C1-C4烷基、C2-C4链烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代链烯基、C2-C4卤代炔基、C3-C6卤代环烷基、卤素、CN、NO2、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷氨基、C2-C8二烷氨基、C3-C6环烷基氨基、C4-C7(烷基)环烷基氨基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷氨基羰基、C3-C8二烷氨基羰基或C3-C6三烷基甲硅烷基所取代;
R2是H;或C1-C6烷基、C2-C6链烯基、C2-C6炔基或C3-C6环烷基,每个基团任选地被一个或多个选自卤素、CN、NO2、羟基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C2-C4烷氧基羰基、C1-C4烷氨基、C2-C8二烷氨基和C3-C6环烷基氨基的取代基取代;或
R2是C2-C6烷基羰基、C2-C6烷氧基羰基、C2-C6烷氨基羰基或C3-C8二烷氨基羰基;
R3是H、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氨基、C2-C8二烷氨基、C3-C6环烷基氨基、C2-C6烷氧基羰基或C2-C6烷基羰基;
R4、R5、R6、R7、R8和R9每个独立地是H、C1-C4烷基或C1-C4卤代烷基;
R10和R11每个独立地是C1-C4烷基或C1-C4烷氧基;
R12是C1-C4烷基、C1-C4烷氧基或任选地被1-3个选自基团R17的取代基取代的苯基;
每个R13独立地选自H、C1-C6烷基、C3-C6环烷基、C1-C6卤代烷基、卤素、CN、C1-C4烷氧基、C2-C4烷氧基羰基、C1-C4烷硫基、C1-C4卤代烷氧基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基和C1-C4卤代烷基磺酰基;
R17是C1-C6烷基,任选地被一个或多个选自卤素、CN、NO2、羟基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C2-C4烷氧基羰基、C1-C4烷氨基、C2-C8二烷氨基和C3-C6环烷基氨基的取代基取代;或苯基,任选地被1-3个选自R17的取代基取代;或
R14是
R15是C1-C6烷基、C3-C6环烷基、C1-C6卤代烷基、卤素、CN、C1-C4烷氧基、C1-C4烷硫基、C1-C4卤代烷氧基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基;或
R15是苯基或吡啶基,任选地被1-3个R17所取代;
R16是H、C1-C6烷基、C1-C6卤代烷基、C3-C6链烯基、C3-C6卤代链烯基、C3-C6炔基或C3-C6卤代炔基;
每个R17独立地是C1-C6烷基、C3-C6环烷基、C1-C6卤代烷基、卤素、CN、C1-C4烷氧基、C1-C4烷硫基、C1-C4卤代烷氧基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基;
m是0、1或2;
n是0、1、2、3或4;
r是0或1;和
s是0、1或2。
本发明还提供了防治无脊椎害虫的方法,包括用生物有效量的通式I化合物、其N-氧化物或化合物的适合的盐(例如,作为此处所描述的组合物)接触无脊椎害虫或其环境。本发明还提供了一种方法,其中,用生物有效量的通式I化合物或含有通式I化合物、其N-氧化物或化合物适合的盐的组合物,和生物有效量的至少一种另外的防治无脊椎害虫的化合物或制剂来接触无脊椎害虫或其环境。
本发明还提供了一种防治无脊椎害虫的组合物,包含生物有效量的通式I化合物、其N-氧化物或化合物的适合的盐,和至少一种另外的选自表面活性剂、固体稀释剂和液体稀释剂的组分。本发明还提供了一种组合物,包含生物有效量的通式I化合物、其N-氧化物或化合物适合的盐和有效量的至少一种另外的生物活性化合物或制剂。
发明详述
在上文中,术语“烷基”可单独使用,或在组合词如“烷硫基”或“卤代烷基”中使用,包括直链或支链烷基,如甲基、乙基、正丙基、异丙基、或不同的丁基、戊基或己基异构体。“链烯基”包括直链或支链链烯基,如乙烯基、1-丙烯基、2-丙烯基、和不同的丁烯基、戊烯基和己烯基异构体。“链烯基”还包括多烯,如1,2-丙二烯基和2,4-己二烯基。“炔基”包括直链或支链炔基,如乙炔基、1-丙炔基、2-丙炔基和不同的丁炔基、戊炔基和己炔基异构体。“炔基”也可包括含有多个三键的部分,如2,5-己二炔基。“烷氧基”包括,例如甲氧基、乙氧基、正丙氧基、异丙氧基和不同的丁氧基、戊氧基和己氧基异构体。“烷硫基”包括支链或直链烷硫基部分,例如甲硫基、乙硫基、和不同的丙硫基和丁硫基异构体。“烷基亚磺酰基”包括烷基亚磺酰基的两个对映体。“烷基亚硫酰基”的实例包括CH3S(O)、CH3CH2S(O)、CH3CH2CH2S(O)、(CH3)2CHS(O)和不同的丁基亚磺酰基异构体。“烷基磺酰基”的实例包括CH3S(O)2、CH3CH2S(O)2、CH3CH2CH2S(O)2、(CH3)2CHS(O)2和不同的丁基磺酰基异构体。“烷氨基”、“二烷氨基”等根据上文的实例进行类似地定义。“环烷基”包括,例如环丙基、环丁基、环戊基、和环己基。术语“环烷基氨基”包括通过氮原子相连的相同的基团,如环戊基氨基和环己基氨基。
与环或环系相关的术语“杂”指的是其中至少一个环原子不是碳的环或环系,可含有1-4个独立地选自氮、氧和硫的杂原子,条件是每个环含有不多于4个氮原子,不多于2个氧原子和不多于2个硫原子。术语“杂芳环或环系”和“芳香族稠合杂二环环系”包括完全芳杂环和其中多环环系中的至少一个环是芳香环(其中,芳香表示满足了休克尔规则)的杂环。杂环或环系可通过取代可用的碳或氮原子上的氢与任一个所述的碳或氮相连。
单独的或在组合词如“卤代烷基”中的术语“卤素”包括氟、氯、溴或碘。另外,当在组合词如“卤代烷基”或“卤代环烷基”中使用时,所述烷基或环烷基可被相同或不同的卤原子部分地或完全地取代。“卤代烷基”的实例包括F3C、ClCH2、CF3CH2和CF3CCl2。术语“卤代链烯基”、“卤代炔基”、“卤代烷氧基”、“卤代烷硫基”等与术语“卤代烷基”类似地进行定义。“卤代链烯基”的实例包括(Cl)2C=CHCH2和CF3CH2CH=CHCH2。“卤代炔基”的实例包括HC≡CCHCl、CF3C≡C、CCl3C≡C和FCH2C≡CCH2。“卤代烷氧基”的实例包括CF3O、CCl3CH2O、HCF2CH2CH2O和CF3CH2O。“卤代烷硫基”的实例包括CCl3S、CF3S、CCl3CH2S和ClCH2CH2CH2S。“卤代烷基亚磺酰基”的实例包括CF3S(O)、CCl3S(O)、CF3CH2S(O)和CF3CF2S(O)。“卤代烷基磺酰基”的实例包括CF3S(O)2、CCl3S(O)2、CF3CH2S(O)2和CF3CF2S(O)2。
“烷基羰基”的实例包括C(O)CH3、C(O)CH2CH2CH3和C(O)CH(CH3)2。“烷氧基羰基”的实例包括CH3OC(=O)、CH3CH2OC(=O)、CH3CH2CH2OC(=O)、(CH3)2CHOC(=O)和不同的丁氧基或戊氧基羰基异构体。“烷氨基羰基”的实例包括CH3NHC(=O)、CH3CH2NHC(=O)、CH3CH2CH2NHC(=O)、(CH3)2CHNHC(=O)和不同的丁氨基或戊氨基羰基异构体。“二烷氨基羰基”的实例包括(CH3)2NC(=O)、(CH3CH2)2NC(=O)、CH3CH2(CH3)NC(=O)、CH3CH2CH2(CH3)NC(=O)和(CH3)2CHN(CH3)C(=O)。
取代基中的碳原子总数用“Ci-Cj”前缀来表示,其中i和j是数字1-8。例如C1-C3烷基磺酰基表示甲磺酰基至丙磺酰基;C2烷氧基烷基表示CH3OCH2;C3烷氧基烷基表示,例如CH3CH(OCH3)、CH3OCH2CH2或CH3CH2OCH2;和C4烷氧基烷基表示共含有4个碳原子的被烷氧基取代的烷基的多种异构体,实例包括CH3CH2CH2OCH2和CH3CH2OCH2CH2。
在上文中,当通式I化合物含有一个或多个杂环时,所有的取代基通过取代任一可用的碳或氮上的氢,通过所述的碳或氮连接于上述环上。
当化合物被带有表示取代基的数目可大于1的下标的所述取代基取代时,所述取代基(当它们大于1时)独立地选自所定义的取代基。另外,当下标表示一个范围,例如(R)i-j时,那么,取代基的数目可选自i和j所包含的整数。
当基团含有可为氢的取代基时,例如R13,那么,当该取代基为氢时,即认为相当于所述基团未被取代。当基团上任选的取代基的数目为0时,例如当n为0时,则认为相当于该基团未被取代。当键被描述为不固定时,那么取代基可通过氢的取代与环上任一可用的碳原子连结。
本发明化合物可以一种或多种立体异构体存在。多种立体异构体包括对映异构体、非对映异构体、阻转异构体和几何异构体。本领域技术人员会懂得,当一种立体异构体相对于其他异构体富集或从其他异构体中分离时,该异构体可显示出更高的活性和/或表现出有利的效果。另外,本领域技术人员知道如何分离、富集、和/或有选择地制备所述的立体异构体。因此,本发明包括选自通式I、其N-氧化物和农业上适合的盐的化合物。本发明化合物可以立体异构体的混合物、单一的立体异构体,或以旋光活性体存在。
本领域技术人员会懂得,不是所有的含氮杂环都能形成N-氧化物,因为氮需要可用的孤对电子来氧化成氧化物;本领域技术人员会识别能形成N-氧化物的含氮杂环。本领域技术人员也知道叔胺可形成N-氧化物。制备杂环和叔胺的N-氧化物的合成方法是本领域技术人员非常熟知的,包括杂环和叔胺用过氧酸如过乙酸和间氯过苯甲酸(MCPBA),过氧化氢,烷基过氧化氢如叔丁基过氧化氢,过硼酸钠和双环氧乙烷(如二甲基双环氧乙烷)氧化。上述制备N-氧化物的方法已经在文献中作了广泛地描述和评论,参见例如:T.L.GilchristinComprehensive Organic Synthesis,vol.7,pp 748-750,S.V.Ley,Ed.,Pergamon Press;M.Tisler和B.Stanovnik in ComprehensiveHeterocyclic Chemistry,vol.3,pp 18-20,A.J.Boulton和A.McKillop,Eds.,Pergamon Press;M.R.Grimmett和B.R.T.Keene in Advances in Heterocyclic Chemistry,vol.43,pp149-161,A.R.Katritzky,Ed.,Academic Press;M.Tisler和B.Stanovnik in Advances in Heterocyclic Chemistry,vol.9,pp 285-291,A.R.Katritzky和A.J.Boulton,Eds.,AcademicPress;和G.W.H.Cheeseman和E.S.G.Werstiuk in Advancesin Heterocyclic Chemistry,vol.22,pp 390-392,A.R.Katritzky和A.J.Boulton,Eds.,Academic Press。
本发明化合物的盐包括与无机酸或有机酸如氢溴酸、盐酸、硝酸、磷酸、硫酸、乙酸、丁酸、富马酸、乳酸、马来酸、丙二酸、草酸、丙酸、水杨酸、酒石酸、4-甲苯磺酸或戊酸的酸加成盐。
为了更高的活性和/或便于合成,优选的化合物是:
优选1.上文通式I的化合物,其N-氧化物和适合的盐,
其中
A是S(O)m;
R1基团中的一个在2-位上与苯环相连,所述的R1是C1-C4烷基、C1-C4卤代烷基、卤素、CN、NO2、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基;
R2和R3每个独立地是H、C1-C4烷基、C2-C4链烯基、C2-C4炔基、C3-C6环烷基、C2-C6烷基羰基或C2-C6烷氧基羰基;
R4、R5、R6和R7每个独立地是H或Me;
R8和R9是H;
R10、R11和R12是Me;
n是1或2;和
r是1。
优选2.优选1的化合物,其中
每个R1独立地是CH3、CF3、OCF3、OCHF2、S(O)pCF3、S(O)pCHF2、CN或卤素;
R2和R3是H;和
p是0、1或2。
优选3.优选2的化合物,其中
每个R13是H、CH3、CF3、CH2CF3、CHF2、OCH2CF3、OCHF2或卤素;
R14是苯基,任选地被1-2个选自R17的取代基取代;或
R14是
R15和R17每个独立地是C1-C4烷基、C1-C4卤代烷基、卤素或CN;
每个R16是CH2CF3或CHF2;和
s是0或1。
优选4.优选3的化合物,其中
每个R13独立地是卤素、OCH2CF3、OCHF2或CF3;
R14是
R17是F、Cl或Br。
优选5.优选4的化合物,其中
R6和R7是H。
优选6.优选5的化合物,其中
J是J-1、J-2、J-4或J-8。
优选7.优选6的化合物,其中
J是J-1;
在2-位上与苯环相连的R1基团是CH3、F、Cl或Br;第二个R1基团在4-位上与苯环相连,所述的第二个R1是CN、CF3、F、Cl、Br或I;
R13独立地是Cl、Br、OCH2CF3、或CF3;和
n是2。
本发明中优选的组合物和使用的优选方法是包含上文优选化合物的组合物和方法。
可通过下面方案1-15所述的一种或多种方法和变化方法制备通式I化合物。在下文通式1-49的化合物中,J、A、R1、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R16、R17、n和r的定义如上文发明概述中所定义,除非另有说明。R1a和R1b与R1定义相同。通式5a、5b和13a化合物是通式5和13化合物的不同子集。
如方案1中所述,通式I化合物可通过将通式2的苯并嗪酮与通式3的胺反应来制备。
方案1
Q是(CR4R5)-(CR6R7)-A-(CR8R9)r-Si(R10R11R12)
反应可单独进行或在多种适合的溶剂包括四氢呋喃、乙醚、二氯甲烷和氯仿中,在室温至溶剂的回流温度的适宜温度下进行。苯并嗪酮与胺反应制备邻氨基苯甲酰胺的一般方法在化学文献中有较好的记载。对于苯并嗪酮化学的评述,参见Jakobsen等人,Biorganicand Medicinal Chemistry 2000,8,2095-2103和其中引用的文献。也参见G.M.Coppola,J.Heterocyclic Chemistry1999,36,563-588。对于通式3胺的合成参见WO 02/062807。
通式2的苯并嗪酮可通过多种方法来制备。在方案2-3中详细地描述了两种特别有用的方法。在方案2中,通式2的苯并嗪酮由通式4的羧酸和通式5的邻氨基苯甲酸直接偶联来制备。
方案2
该方案包括在叔胺如三乙胺或吡啶的存在下向通式4的吡唑羧酸中连续地加入甲磺酰氯,继而加入通式5的邻氨基苯甲酸,然后再加入叔胺和甲磺酰氯。该方法一般得到较高收率的苯并嗪酮,在实施例1中进行更详细地阐述。
方案3描述了通式2的苯并嗪酮的另一制备方法,包括通式7的酰基氯与通式6的靛红酸酐偶联直接获得通式2的苯并嗪酮。
方案3
溶剂如吡啶或吡啶/乙腈对于该反应是适合的。通式7的酰基氯可通过已知的方法例如用亚磺酰氯或草酰氯氯化从通式4对应的酸得到。
通式5的邻氨基苯甲酸可通过多种已知的方法来获得。上述的许多化合物是已知的。如方案4中所示,含有氯、溴或碘的R1b取代基的通式5b的邻氨基苯甲酸可通过通式5a的未取代的邻氨基苯甲酸与N-氯琥珀酰亚胺(NCS)、N-溴琥珀酰亚胺(NBS)或N-碘琥珀酰亚胺(NIS)分别在适合的溶剂如N,N-二甲基甲酰胺(DMF)中直接卤化来制备。
通式5b的邻氨基苯甲酸代表通式I化合物的一组优选的中间体。
方案4
R1b是Cl,Br或I
如方案5所述,通式6的靛红酸酐可通过通式9的靛红来获得。
方案5
通式9的靛红由通式8的苯胺衍生物根据下面文献中的方法来获得,如F.D.Popp,Adv.Heterocycl.Chem.1975,18,1-58和J.F.M.DaSilva等人,Journal of the Brazilian Chemical Society2001,12(3),273-324。靛红9与过氧化氢的氧化一般获得较高收率的相应的靛红酸酐6(G.Reissenweber and D.Mangold,Angew.Chem.Int.Ed.Engl.1980,19,222-223)。靛红酸酐也可由邻氨基苯甲酸5通过许多已知的方法来获得,包括5与光气或光气等价物的反应。
杂环酸4,其中J等于任选的取代的吡唑、吡咯、吡啶或嘧啶,包括J-1至J-8中的那些酸。更优选的类似物包括由被R14如任选的取代的苯基或吡啶基取代的吡唑酸衍生的衍生物。每种代表性实例的合成方法在方案6-15中详述。
通式13的代表性吡唑羧酸的合成在方案6中进行描述,涉及其中的R14是2-吡啶基并与氮原子相连的通式J-1。吡唑10和通式11的2-卤代吡啶的反应得到较高收率的1-吡啶基吡唑12,并具有所要区域化学的良好专一性。通式12的化合物用二异丙基氨基锂(LDA)金属化,继而用二氧化碳萃灭锂盐得到通式13的吡唑酸。
方案6
其中R13是CF3、Cl或Br的通式10的起始吡唑是已知的化合物。其中R13是CF3的吡唑10可通过文献中的方法来制备(J.FluorineChem.1991,53(1),61-70)。其中R13是Cl或Br的吡唑10也可以通过文献中的方法(H.Reimlinger and A.Van Overstraeten,Chem.Ber.1966,99(10),3350-7)来制备。制备其中R13是Cl或Br的10的另一有用的方法在方案7中描述。氨磺酰吡唑14与正丁基锂金属化,继而阴离子用六氯乙烷(R13为Cl)或1,2-二溴四氯乙烷(R13为Br)直接卤化得到卤化的衍生物15。在室温用三氟乙酸(TFA)完全去除掉氨磺酰基,高收率地分别得到其中R13是Cl或Br的吡唑10。
方案7
通式20的有代表性的吡唑酸的合成描述在方案8中,涉及其中的R14是2-吡啶基并与吡唑环的5位相连的通式J-2。通式18的二甲基氨基亚基酮酯与取代的肼反应得到吡啶基吡唑19。优选的R16取代基包括烷基和卤代烷基,特别优选三氟乙基。酯19通过标准的水解转化为通式20的酸。
方案8
通式22的有代表性的吡唑酸的合成描述在方案9中,涉及其中R14是2-吡啶基并连接在吡唑环3位上的通式J-3和通式20的另一合成方法。通式18的二甲基氨基亚基酮酯与肼反应得到吡唑21。吡唑21与烷基化试剂R16-LG(其中LG是离去基团如卤素(如Br、I)、OS(O)2CH3(甲基磺酸酯)、OS(O)2CF3、OS(O)2Ph-p-CH3(对甲苯磺酸盐)等)反应得到吡啶基吡唑的混合物。该吡唑异构体的混合物通过色谱法迅速地分离,转化为相应的酸20和22。优选的R16取代基包括烷基和卤代烷基。
方案9
通式27吡咯酸的合成描述在方案10中,涉及其中R14是2-吡啶基并连结在吡咯环的氮原子上的通式J-4。3-氯-2-氨基吡啶24是已知的化合物(参见J.Heterocycl.Chem.1987,24(5),1313-16)。由2-氨基吡啶23方便地制备24包括保护、邻位金属化、氯化和随后的去保护。通式24的化合物用2,5-二甲氧基四氢呋喃处理得到吡咯25。吡咯25对通式26醛的甲酰化可利用标准的Vilsmeier-Haack甲酰化条件来完成。通式26化合物用N-卤代琥珀酰亚胺(NXS)的卤化优选发生在吡咯环的4位上。卤代的醛氧化得到通式27的吡啶基吡咯酸。氧化可利用多种标准的氧化条件来完成。
方案10
通式33吡咯酸的合成描述在方案11中,涉及其中R14是苯基或2-吡啶基并与吡咯环的2位相连的通式J-5。通式30的丙二烯与通式29的芳基磺酰胺环化加成(参见Pavri,N.P.;Trudell M.L.J.Org.Chem.1997,62,2649-2651)得到通式31的吡咯啉。通式31的吡咯啉用氟化四丁铵(TBAF)处理得到通式32的吡咯。吡咯32与烷基化试剂R16-LG(其中,LG是上文所定义的离去基团)反应随后水解得到通式33的吡咯酸。
方案11
其中Z是N或CH
通式36吡咯酸的合成描述在方案12中,涉及其中R14是2-氯苯基或3-氯-2-吡啶基的通式J-6。通式34的肉桂酯与甲苯磺酰基甲基胩(TosMIC)反应得到通式35的吡咯。该方法重要的参考资料参见Xu,Z.等人,J.Org.Chem.1998,63,5031-5041。通式35的化合物与通式R14-LG(其中,LG是上文所定义的离去基团)的烷基化试剂反应,随后酯水解得到通式36的吡咯酸。
方案12
通式42吡啶酸的合成描述在方案13中,涉及通式J-7。该方法包括由β-酮酯40和4-氨基丁烯酮39的已知的合成吡啶的方法。取代基R13和R14包括例如苯基、烷基和卤代烷基。
方案13
通式46的嘧啶酸的合成描述在方案14中,涉及通式J-8。该方法包括已知的方法由亚乙烯基酮酯44和脒合成嘧啶。取代基R13和R14包括例如苯基、烷基和卤代烷基。
方案14
作为方案6所述方法的另一选择,其中R13是Cl或Br的通式13a吡唑羧酸可通过方案15所述的方法来制备。肼基吡啶47与马来酸二乙酯反应得到吡唑酮48。用三氯氧化磷或三溴氧化磷氯化或溴化得到通式49的卤代衍生物。通式49化合物的氧化任选地在酸的存在下进行得到吡唑酯,继而将酯官能团转化为羧酸得到通式13a化合物。氧化剂可以是过氧化氢、有机过氧化物、过二硫酸钾、过二硫酸钠、过二硫酸铵、单过硫酸钾(如Oxone)或高锰酸钾。
方案15
应当认识到上述的制备通式I化合物的一些试剂和反应条件可能与中间体中存在的某些官能团不相容。在上述情况下,保护/去保护程序或官能团互变加入到合成过程中将有助于获得所要的产品。保护基的使用和选择对化学合成方面的技术人员来说是显而易见的(参见例如Greene,T.W.;Wuts,P.G.M.Protective Groups in OrganicSynthesis 2nd ed.;Wiley:New York,1991)。本领域技术人员知道在一些情况下,任一单独方案中所描述的一个给定的试剂引入后,可能还需完成没有详细描述的另外的路线合成步骤,以完成通式I化合物的合成。本领域技术人员也知道按顺序完成上述方案中阐述的步骤的组合可能是必须的,除非含有制备通式I化合物的特殊次序。
本领域技术人员还应认识到,此处所述的通式I化合物和中间体可进行多种亲电、亲核、自由基、有机金属、氧化、和还原反应来增加取代基或修饰现有的取代基。
不用进一步推敲,可以相信,本领域技术人员利用前面所描述的内容能够将本发明利用到其最完整的程度。因此,下面的实施例只是用来解释说明,而不是以任何方式限制本发明。百分数是重量百分数,除非是色谱法溶剂混合物或另有其他说明。除非有其他说明,色谱溶剂混合物的份和百分数是体积份和体积百分数。1H NMR谱用ppm根据来自四甲基硅烷的低磁场进行记录;s是单峰,d是双峰,t是三重峰,q是四重峰,m是多重峰,dd是双二重峰,dt是双三重峰,brs是宽单峰。
实施例1
制备3-溴-N-[4-氯-2-甲基-6-[[[1-甲基-2-[[(三甲基甲硅烷基)甲基]硫代]乙基]氨基]羰基]苯基]-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酰胺
步骤A:制备2-(3-氯-2-吡啶基)-5-氧代-3-吡唑烷甲酸乙酯
向配有机械搅拌器、温度计、附加漏斗、回流冷凝管和氮气入口的2-L四颈烧瓶中加入无水乙醇(250mL)和乙醇钠(21%,190mL,0.504mol)的乙醇溶液。该混合物在约83℃加热至回流。然后用3-氯-2(1H)-吡啶酮腙(68.0g,0.474mol)处理。该混合物在5分钟的时间内重新加热至回流。黄色的浆状物然后用马来酸二乙酯(88.0mL,0.544mol)在5分钟内逐滴地处理。在加入过程中回流率显著增加。在加入结束时,所有的起始物质都溶解。所得的橙红色溶液在回流温度维持10分钟。冷却至65℃后,反应混合物用冰乙酸(50.0mL,0.873mol)处理。沉淀形成。混合物用水(650mL)稀释,造成沉淀溶解。橙色溶液在冰浴中冷却。产物在28℃开始沉淀。浆状物在约2℃维持2小时。产物通过过滤分离,用含水乙醇(40%,3×50mL)洗涤,然后在过滤器上风干约1小时。获得题列化合物,为高质量的结晶的浅橙色粉末(70.3g,55%的收率)。通过1H NMR观测没有明显的杂质。
1H NMR(DMSO-d6)δ1.22(t,3H),2.35(d,1H),2.91(dd,1H),4.20(q,2H),4.84(d,1H),7.20(dd,1H),7.92(d,1H),8.27(d,1H),10.18(s,1H)。
步骤B:制备3-溴-1-(3-氯-2-吡啶基)-4,5-二氢-1H-吡唑-5-甲酸乙酯
向配有机械搅拌器、温度计、回流冷凝管和氮气入口的1-L四颈烧瓶中加入乙腈(400mL)、2-(3-氯-2-吡啶基)-5-氧代-3-吡唑烷甲酸乙酯(即步骤A的产物)(50.0g,0.185mol)和三溴氧化磷(34.0g,0.119mol)。橙色浆状物在83℃加热至回流20分钟。所得的浑浊的橙色溶液在回流温度维持75分钟,此时形成稠的褐色结晶沉淀。用蒸馏头替换回流冷凝管,收集不透明的无色蒸馏液(300mL)。向配有机械搅拌器的第二个1-L四颈烧瓶中加入碳酸氢钠(45g,0.54mol)和水(200mL)。浓缩的反应混合物5分钟内加入到碳酸氢钠浆状物中。所得的两相混合物剧烈地搅拌5分钟,此时气体的生成停止。混合物用二氯甲烷(200mL)稀释,然后搅拌75分钟。混合物用5gCelite545硅藻土助滤剂处理,然后过滤分出褐色焦油物质。滤液转移到分液漏斗中。分出褐色有机层(400mL),然后用硫酸镁(15g)和DarcoG60活性炭(2.0g)处理。所得的浆状物磁力搅拌15分钟,然后过滤分出硫酸镁和炭。绿色的滤液用硅胶(3g)处理并搅拌几分钟。深蓝绿色的硅胶通过过滤分出,滤液通过旋转蒸发仪浓缩。产物为浅琥珀色的油(58.6g,95%的收率),静置结晶。通过1H NMR可观测到的仅有的杂质为0.3%的乙腈。
1H NMR(DMSO-d6)δ1.15(t,3H),3.29(dd,1H),3.60(dd,1H),4.11(q,2H),5.20(dd,1H),6.99(dd,1H),7.84(d,1H),8.12(d,1H)。
步骤C:制备3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酸乙酯
向配有机械搅拌器、温度计、回流冷凝管和氮气入口的1-L四颈烧瓶中加入3-溴-1-(3-氯-2-吡啶基)-4,5-二氢-1H-吡唑-5-甲酸乙酯(即步骤B的产物)(40.2g,0.121mol)、乙腈(300mL)和硫酸(98%,13.0mL,0.245mol)。该混合物由于加入硫酸自热由22升至36℃。搅拌几分钟后,混合物用过二硫酸钾(48.0g,0.178mol)处理。浆状物在84℃加热回流2小时。当所得的橙色浆状物仍温热(50-65℃)时,过滤分出白色沉淀。滤饼用乙腈(2×50mL)洗涤。滤液通过旋转蒸发仪浓缩至约200mL。向配有机械搅拌器的第二个1-L四颈烧瓶中加入水(400mL)。将浓缩的反应物质约5分钟内加入到水中。产物过滤分离,顺次用含水乙腈(20%,100mL)和水(75mL)洗涤,然后在过滤器上风干1小时。产物为结晶的橙色粉末(36.6g,90%的收率)。通过1H NMR可观测到的仅有的杂质为约1%的未知物和0.5%的乙腈。
1H NMR(DMSO-d6)δ1.09(t,3H),4.16(q,2H),7.35(s,1H),7.72(dd,1H),8.39(d,1H),8.59(d,1H)。
步骤D:制备3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酸
向配有机械搅拌器、温度计和氮气入口的300-mL四颈烧瓶中加入3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酸乙酯(即步骤C的产物)(98.5%是纯的,25.0g,0.0756mol)、甲醇(75mL)、水(50mL)、和氢氧化钠颗粒(3.30g,0.0825mol)。由于加入氢氧化钠,混合物自热由29升至34℃,起始物质开始溶解。在室温条件下搅拌90分钟后,所有的起始物质都溶解。所得的暗橙色溶液通过旋转蒸发仪浓缩至约90mL。浓缩的反应混合物然后用水(160mL)稀释。水溶液用乙醚(100mL)萃取。然后,水层转移到配有磁力搅拌器的500-mL锥形烧瓶中。该溶液在约10分钟内用浓盐酸(8.50g,0.0839mol)逐滴地处理。产物过滤分离,用水(2×40mL)重新打浆,盖子用水(25mL)洗涤一次,然后在过滤器上风干2小时。产物为结晶的褐色粉末(20.9g,91%的收率)。通过1H NMR可观测到的仅有的杂质为约0.8%的未知物和0.7%的乙醚。
1H NMR(DMSO-d6)δ7.25(s,1H),13.95(br s,1H),8.56(d,1H),8.25(d,1H),7.68(dd,1H)。
步骤E:制备2-[3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-基]-6-氯-8-甲基-4H-3,1-苯并嗪-4-酮
甲基磺酰氯(1.0mL,1.5g,13mmol)溶解在乙腈(10mL)中,混合物冷却至-5℃。在-5至0℃和5分钟内逐滴地加入3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酸(即步骤D的产物)(3.02g,10mmol)和吡啶(1.4mL,1.4g,17mmol)的乙腈(10mL)溶液。在加入的过程中形成浆状物。混合物在该温度搅拌5分钟,然后加入2-氨基-3-甲基-5-氯苯甲酸(1.86g,10mmol)和吡啶(2.8mL,2.7g,35mmol)在乙腈(10mL)中的混合物,用更多的乙腈(5mL)漂洗。混合物在-5至0℃搅拌15分钟,然后在-5至0℃5分钟内逐滴地加入甲基磺酰氯(1.0mL,1.5mL,13mmol)的乙腈(5mL)溶液。反应混合物再在该温度搅拌15分钟,然后缓慢地升至室温,搅拌4小时。逐滴地加入水(20mL),混合物搅拌15分钟。然后过滤混合物,固体用2∶1乙腈-水(3×3mL)洗涤,然后用乙腈(2×3mL)洗涤,氮气下干燥得到题列产物,为浅黄色粉末,4.07g(粗收率90.2%),熔点203-205℃。利用ZorbaxRX-C8色谱柱(4.6mm×25cm,洗脱剂25-95%乙腈/pH3水),产物的HPLC显示对应于题列化合物的主峰,具有95.7%的总色谱峰区域。
1H NMR(DMSO-d6)δ1.72(s,3H)7.52(s,1H),7.72-7.78(m,2H),7.88(m,1H),8.37(dd,1H),8.62(dd,1H)。
步骤F:制备3-溴-N-[4-氯-2-甲基-6-[[[1-甲基-2-[[(三甲基甲硅烷基)甲基]硫代]乙基]氨基]羰基]苯基]-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酰胺
向2-[3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-基]-6-氯-8-甲基-4H-3,1-苯并嗪-4-酮(即步骤E的苯并嗪酮产物)(0.23g,0.51mmol)的四氢呋喃溶液中加入1-三甲基甲硅烷基甲硫基-2-丙胺(0.103g,0.58mmol),反应混合物加热至80℃3小时,然后冷却至室温。将四氢呋喃溶剂减压下蒸发,残余固体通过硅胶色谱法用己烷/乙酸乙酯作洗脱剂(5∶1)得到题列化合物,一种本发明的化合物,白色固体(73mg),m.p.151-153℃。
1H NMR(CDCl3)δ0.097(s,9H),1.30(d,3H),1.83(s,2H),2.19(s,3H),2.70(d,2H),4.32(m,1H),6.22(bd,1H),7.22(m,2H),7.05(s,1H),7.28(m,2H),7.38(dd,1H),7.84(dd,1H),8.45(dd,1H),10.10(bs,1H)。
通过此处所描述的方法结合本领域已知的方法可制备下表1-8中的化合物。在表中使用的缩写如下:Me是甲基,CN是氰基。
表1
R1a | R1b | R13 | R17 | m | R1a | R1b | R13 | R17 | m |
MeMeMeMeMeClClCl | ClBrFICNClBrF | ClClClClClClClCl | ClClClClClClClCl | 00000000 | MeMeMeMeMeClClCl | ClBrFICNClBrF | ClClClClClClClCl | ClClClClClClClCl | 11111111 |
R1a | R1b | R13 | R17 | m | R1a | R1b | R13 | R17 | m |
ClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBrBrBrBr | ICNClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBrFICN | ClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | 0000000000000000000000000000000000000 | ClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBrBrBrBr | ICNClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBrFICN | ClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | 1111111111111111111111111111111111111 |
R1a | R1b | R13 | R17 | m | R1a | R1b | R13 | R17 | m |
MeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMeMeCl | ClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClClBrFICNCl | OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3ClClClClClClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClBrClClClClClCl | 0000000000000000000000000000000222222 | MeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMeMeCl | ClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClClBrFICNCl | OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3ClCF3CF3CF3CF3CF3CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClBrClClClClClCl | 1111111111111111111111111111111222222 |
R1a | R1b | R13 | R17 | m | R1a | R1b | R13 | R17 | m |
ClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMeBrBrBr | BrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBrF | ClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | 22222222222222222222222222222222 | ClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBrBrBrBrClClClClClBrBr | BrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNICN | CF3CF3CF3CF3CF3CF3CF3CF3CF3OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCHF2OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | 2222222222222222222222222222222 |
表2
R1a | R1b | R16 | m | R1a | R1b | R16 | m |
MeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBr | ClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBr | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3 | 000000000000000000000000000 | MeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBr | ClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBr | CHF2CHF2CHF2CHP2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CF2CF3CH2CF3CH2CF3 | 111111111111111111111111111 |
R1a | R1b | R16 | m | R1a | R1b | R16 | m |
BrBrBrMeMeMeMeMeClClClClClBrBrBrBrBr | FICNClBrFICNClBrFICNClBrFICN | CH2CF3CH2CF3CH2CF3CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 | 000222222222222222 | BrBrBrMeMeMeMeMeClClClClClBrBrBrBrBr | FICNClBrFICNClBrFICNClBrFICN | CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3 | 111222222222222222 |
表3
R1a | R1b | R16 | m | R1a | R1b | R16 | m |
MeMeMeMeMe | ClBrFICN | CHF2CHF2CHF2CHF2CHF2 | 00000 | MeMeMeMeMe | ClBrFICN | CHF2CHF2CHF2CHF2CHF2 | 11111 |
R1a | R1b | R16 | m | R1a | R1b | R16 | m |
ClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBr | ClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBr | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHf2CHF2CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 | 0000000000000000000000000222222222222 | ClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBr | ClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBr | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3 | 1111111111111111111111111222222222222 |
R1a | R1b | R16 | m | R1a | R1b | R16 | m |
BrBrBr | FICN | CHF2CHF2CHF2 | 222 | BrBrBr | FICN | CH2CF3CH2CF3CH2CF3 | 222 |
表4
R1a | R1b | R13 | m | R1a | R1b | R13 | m |
MeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMe | ClBrFICNClBrFICNClBrFICNClBrFICN | ClClClClClClClClClClClClClClClBrBrBrBrBr | 00000000000000000000 | MeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMe | ClBrFICNClBrFICNClBrFICNClBrFICN | ClClClClClClClClClClClClClClClBrBrBrBrBr | 11111111111111111111 |
R1a | R1b | R13 | m | R1a | R1b | R13 | m |
ClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBrBrBrBr | ClBrFICNClBrFICNClBrFICNClBrFICNClBrFICN | BrBrBrBrBrBrBrBrBrBrClClClClClClClClClClClClClClCl | 0000000000222222222222222 | ClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBrBrBrBr | ClBrFICNClBrFICNClBrFICNClBrFICNClBrFICN | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | 1111111111222222222222222 |
表5
R1a | R1b | R16 | m | R1a | R1b | R16 | m |
MeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBr | ClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBr | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3 | 000000000000000000000000000 | MeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBr | ClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBr | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3 | 111111111111111111111111111 |
R1a | R1b | R16 | m | R1a | R1b | R16 | m |
BrBrBrMeMeMeMeMeClClClClClBrBrBrBrBr | FICNClBrFICNClBrFICNClBrFICN | CH2CF3CH2CF3CH2CF3CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 | 000222222222222222 | BrBrBrMeMeMeMeMeClClClClClBrBrBrBrBr | FICNClBrFICNClBrFICNClBrFICN | CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3 | 111222222222222222 |
表6
R1a | R1b | R16 | m | R1a | R1b | R16 | m |
MeMeMeMeMe | ClBrFICN | CHF2CHF2CHF2CHF2CHF2 | 00000 | MeMeMeMeMe | ClBrFICN | CHF2CHF2CHF2CHF2CHF2 | 11111 |
R1a | R1b | R16 | m | R1a | R1b | R16 | m |
ClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBr | ClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBr | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 | 0000000000000000000000000222222222222 | ClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBr | ClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBr | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3 | 1111111111111111111111111222222222222 |
R1a | R1b | R16 | m | R1a | R1b | R16 | m |
BrBrBr | FICN | CHF2CHF2CHF2 | 222 | BrBrBr | FICN | CH2CF3CH2CF3CH2CF3 | 222 |
表7
R1a | R1b | R13 | m | R1a | R1b | R13 | m |
MeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMeCl | ClBrFICNClBrFICNClBrFICNClBrFICNCl | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3 | 000000000000000000000 | MeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMeCl | ClBrFICNClBrFICNClBrFICNClBrFICNCl | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3 | 111111111111111111111 |
R1a | R1b | R13 | m | R1a | R1b | R13 | m |
ClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBrBrBrBr | BrFICNClBrFICNClBrFICNClBrFICNClBrFICN | CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | 000000000222222222222222 | ClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBrBrBrBr | BrFICNClBrFICNClBrFICNClBrFICNClBrFICN | CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3 | 111111111222222222222222 |
表8
R1a | R1b | R13 | m | R1a | R1b | R13 | m |
MeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBr | ClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBr | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3 | 000000000000000000000000000 | MeMeMeMeMeClClClClClBrBrBrBrBrMeMeMeMeMeClClClClClBrBr | ClBrFICNClBrFICNClBrFICNClBrFICNClBrFICNClBr | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3 | 111111111111111111111111111 |
R1a | R1b | R13 | m | R1a | R1b | R13 | m |
BrBrBrMeMeMeMeMeClClClClClBrBrBrBrBr | FICNClBrFICNClBrFICNClBrFICN | CH2CF3CH2CF3CH2CF3CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 | 000222222222222222 | BrBrBrMeMeMeMeMeClClClClClBrBrBrBrBr | FICNClBrFICNClBrFICNClBrFICN | CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3CH2CF3 | 111222222222222222 |
剂型/应用
本发明化合物一般与农业或非农业使用的适合的载体包括至少一种液体稀释剂、固体稀释剂或表面活性剂制成剂型或组合物来使用。剂型或组合物成分的选择应与活性成分的物理性质,施用方式和环境因素如土壤类型、湿度和温度相适应。有用的剂型包括液剂如溶液(包括乳油)、悬浮剂、乳剂(包括微乳剂和/或悬乳剂)等,它们可任选的浓缩成胶状物。有用的剂型还包括固体剂型如粉剂、粉末、颗粒剂、丸剂、片剂、膜剂等,它们可以是水分散性的(“可湿性的”)或水溶性的。活性成分可被(微)胶囊化再进一步制成悬浮剂或固体剂型;另外,活性成分的整个剂型也可被胶囊化(或“包被”)。胶囊化可以控制或延缓活性成分的释放。可喷雾剂型可在适当的介质中冲稀,按每公顷约一至几百升的喷雾体积使用。高浓度的组合物主要用于进一步加工的中间产品。
剂型一般含有有效量的活性成分、稀释剂和表面活性剂,按以下的大约范围,总和为100%重量。
重量百分数 | |||
活性成分 | 稀释剂 | 表面活性剂 | |
水分散性和水溶性的颗粒剂、片剂和粉剂悬浮剂、乳剂、溶液(包括乳油)粉剂颗粒剂和丸剂高浓度组合物 | 5-905-501-250.01-9990-99 | 0-9440-9570-995-99.990-10 | 1-150-150-50-150-2 |
一般的固体稀释剂描述在Watkins等人,Handbook ofInsecticide Dust Diluents and Carriers,2nd Ed.,Dorland Books,Caldwell,New Jersey中。一般的液体稀释剂描述在Marsden,Solvents Guide,2nd Ed.,Interscience,New York,1950中。McCutcheon’s Detergents and Emulsifiers Annual,Allured Publ.Corp.,Ridgewood,New Jersey,以及Sisely and Wood,Encyclopedia of Surface Active Agents,Chemica Publ.Co.,Inc.,New York,1964中列出了表面活性剂及应用推荐。所有的剂型都可含有少量的添加剂以减少泡沫、结饼、腐蚀、微生物的生长等,或增稠剂以增加粘度。
表面活性剂包括,例如,聚乙氧基化醇、聚乙氧基化烷基酚、聚乙氧基化脱水山梨醇脂肪酸酯、磺化丁二酸二烷基酯、硫酸烷基酯、烷基苯磺酸盐、有机硅烷、N,N-二烷基牛磺酸酯、木质素磺酸盐、萘磺酸盐蚁醛缩合物、聚羧酸酯和聚氧乙烯/聚氧丙烯嵌段共聚物。固体稀释剂包括,例如粘土如膨润土、蒙脱石、硅镁土和高岭土,淀粉、糖、二氧化硅、滑石、硅藻土、尿素、碳酸钙、碳酸钠和碳酸氢钠,和硫酸钠。液体稀释剂包括,例如,水、N,N-二甲基甲酰胺、二甲亚砜、N-烷基吡咯啉酮、乙二醇、聚丙二醇、石蜡、烷基苯、烷基萘、橄榄油、蓖麻油、亚麻籽油、桐油、芝麻油、玉米油、花生油、棉籽油、大豆油、菜籽油和可可油、脂肪酸酯、酮类如环己酮、2-庚酮、异佛尔酮和4-羟基-4-甲基-2-戊酮、和醇类如甲醇、环己醇、十二烷醇和四氢呋喃醇。
溶液,包括乳油,可以通过简单地混合各成分来制备。粉剂和粉末可通过混合,通常在锤磨机或流能磨中研磨来制备。悬浮剂通常通过湿磨来制备;参见,例如U.S.3,060,084。颗粒剂和丸剂可通过将活性物质喷到刚制成的颗粒载体上或通过造粒技术来制备。参见Browning,“Agglomeration”,Chemical Engineering,December4,1967,pp 147-48,Perry’s Chemical Engineer’s Handbook,4thEd.,McGraw-Hill,New York,1963,8-57页和下面的PCT公开文本WO 91/13546。丸剂可根据U.S.4,172,714中所述进行制备。水分散性和水溶性颗粒剂根据U.S.4,144,050、U.S.3,920,442和DE3,246,493中所述的方法制备。片剂可根据U.S.5,180,587、U.S.5,232,701和U.S.5,208,030中所述的方法来制备。膜剂可根据GB2,095,558和U.S.3,299,566中所述的方法来制备。
关于剂型领域的更多信息参见T.S.Woods,“The Formulator’Toolbox-Product Forms for Modern Agriculture”in PesticideChemistry and Bioscience,The Food-Environment Challenge,T.Brooks和T.R.Roberts,Eds.,Proceeding of the 9thInternational Congresson Pestctide Chemistry,The RoyalSociety of Chemistry,Cambridge,1999,pp.120-133。也可参见U.S.3,235,361,6栏16行至7栏19行和实施例10-41;U.S.3,309,192,5栏43行至7栏62行和实施例8、12、15、39、41、52、53、58、132、138-140、162-164、166、167和169-182;U.S.2,891,855,3栏66行至5栏17行和实施例1-4;Klingman,WeedControl as a Science,John Wiley和Sons,Inc.,New York,1961,pp81-96;和Hance等人,Weed Control Handbook,8th Ed.,Blackwell Scientific Publications,Oxford,1989。
在以下实施例中,所有百分数均以重量计,所有剂型都用常规方法制备。化合物号参见索引表A中的化合物。
实施例A
可湿性粉剂
化合物1 65.0%
十二烷基酚聚乙二醇醚 2.0%
木质素磺酸钠 4.0%
硅铝酸钠 6.0%
蒙脱土(煅烧的) 23.0%。
实施例B
颗粒剂
化合物1 10.0%
硅镁土颗粒(低挥发物,0.71/0.30mm,
U.S.S.No.25-50筛)90.0%。
实施例C
挤压丸剂
化合物1 25.0%
无水硫酸钠 10.0%
粗木质素磺酸钙 5.0%
烷基萘磺酸钠 1.0%
钙/镁膨润土 59.0%。
实施例D
乳油
化合物1 20.0%
油状可溶性磺酸盐和聚氧乙烯醚的混合物 10.0%
异佛尔酮 70.0%。
实施例E
颗粒剂
化合物1 0.5%
纤维素 2.5%
乳糖 4.0%
玉米粉 93.0%
本发明化合物具有良好的代谢性和/或土壤残留模式,并表现出防治农业和非农业无脊椎害虫谱的活性。(在说明书的上下文中,“无脊椎害虫防治”是指抑制无脊椎害虫的生长(包括死亡),使得害虫所引起的取食或其他的伤害或损害明显减少;相关的表述进行类似的定义。)就本说明书而言,术语“无脊椎害虫”包括经济重要的节肢动物、腹足动物和线虫害虫。术语“节肢动物”包括昆虫、螨、蜘蛛、蝎子、蜈蚣、千足虫、球潮虫和综合纲害虫(symphylans)。术语“腹足动物”包括蜗牛、鼻涕虫和其他的有柱腹足目动物。术语“线虫”包括所有的蠕虫如蛔虫、犬恶丝虫,和植食性线虫(线虫纲)、吸虫(Tematoda)、棘头纲、和绦虫(真绦虫亚纲)。本领域的技术人员会认识到不是所有的化合物对所有的害虫都是等效的。本发明的化合物对经济上重要的农业和非农业害虫表现出了活性。“农业”指的是大田作物如粮食和纤维的生产,包括谷类作物(例如小麦、燕麦、大麦、黑麦、稻、玉米)、大豆、蔬菜作物(例如,莴苣、甘蓝、西红柿、菜豆)、马铃薯、甘薯、葡萄、棉花、和果树(例如,梨果、核果和柑桔类水果)的生长。术语“非农业”指的是其他园艺(例如,森林、温室、苗圃或不在大田中生长的观赏植物)、公共(人类)和动物健康、家用和商业建筑、家庭和储藏产品设备或害虫。鉴于无脊椎害虫的防治谱和经济重要性,通过防治无脊椎害虫来保护(由无脊椎害虫造成的损伤或伤害)农作物棉花、玉米、大豆、稻、蔬菜作物、马铃薯、甘薯、葡萄和果树是本发明优选的实施方案。农业或非农业害虫包括鳞翅目幼虫,例如夜蛾科(例如草地粘虫(Spodopterafugiperda J.E.Smith)、甜菜夜蛾(Spodoptera exigua Hübner)、小地老虎(Agrotis ipsilon Hufnagel)、粉纹夜蛾(Trichoplusiani Hübner)、烟夜蛾(Heliothis virescens Fabricius))的粘虫、毛虫、尺蠖、和棉铃虫(heliothines);螟蛾科(例如欧洲玉米螟(Ostrinia nubilalis Hübner)、脐橙虫(Amyelois transitellaWalker)、玉米根网螟(Crambus caliginosellus Clemens)、草坪网螟(Herpetogramma licarsisalis Walker))的钻心虫、鞘蛾幼虫、结网毛虫、锥虫(coneworm)、卷叶菜虫、和雕叶虫;卷叶蛾科(例如苹果蠹蛾(Cydia pomonella Linnaeus)、葡萄小卷蛾(Endopizaviteana Clemens),梨小食心虫(Grapholita molesta Busck))中的卷叶蛾、芽虫、种子虫和果虫;和许多其他经济重要的鳞翅目害虫(如小菜蛾(Plutella xylostella Linnaeus)、棉红铃虫(Pectinophora gosypiella Saunders)、卷叶蛾(Lymantria disparLinnaeus));蜚蠊目的若虫和成虫,包括小蠊科和蜚蠊科中的蜚蠊(例如东方蜚蠊(Blatta orientalis Linnaeus),亚洲蜚蠊(Blatellaasahinai Mizukubo)、德国小蠊(Blattella germanica Linnaeus),长须蜚蠊(Supella longipalpa Fabricius),美洲大蠊(Periplanetaamericana Linnaeus)、褐色大蠊(Periplaneta brunneaBurmeister)、马德拉蜚蠊(Leucophaea maderae Fabricius));鞘翅目的食叶幼虫和成虫,包括长角象虫科、豆象科和象甲科的象鼻虫(例如棉象甲(Anthonomus grandis Boheman)、稻象甲(Lissorhoptrus oryzophilus Kuschel)、谷象(Sitophilusgranarius Linnaeus)、稻二点象甲(Sitophilus oryzaeLinnaeus));叶甲科(例如马铃薯甲虫(Leptinotarsa decemlineataSay)、玉米幼芽根叶甲(Diabrotica virgifera virgiferaLeConte))的喜跳甲、黄守瓜、食根虫、金花虫、马铃薯甲虫和潜叶虫;金龟科的金龟子和其他甲虫(例如日本弧丽金龟(Popilliajaponica Newman)和欧洲金龟(Rhizotrogus majalisRazoumowsky));皮蠹科的红缘皮蠹;叩头虫科的切根虫;棘胫小蠹科的小蠹虫和拟步行虫科的面粉甲虫。此外,农业和非农业害虫还包括革翅目的成虫和幼虫,包括球螋科的蠼螋(例如欧洲球螋(Forficulaauricularia Linnaeus)、黑球螋(Chelisoches morio Fabricius));半翅目和同翅目的成虫和若虫,例如盲蝽科的盲蝽象,蝉科的蝉,大叶蝉科的叶蝉(如Empoasca spp.),蜡蝉科和飞虱科的飞虱,角蝉科的角蝉,木虱科的木虱,粉虱科的粉虱,蚜科的蚜虫,根瘤蚜科的根瘤蚜,粉蚧科的粉蚧,蚧科、盾蚧科、绵蚧科的介壳虫,网蝽科的网蝽,蝽科的蝽象,长蝽科的长蝽(例如Blissus spp.)和其他实蝽,沫蝉科的沫蝉,缘蝽科的缘蝽和红蝽科的红蝽和棉红蝽。也包括蜱螨目的成虫和幼虫,例如叶螨科(例如苹果全爪螨(Panonychus ulmiKoch)、二点叶螨(Tetranychus urticae Koch)、麦克旦尼氏螨(Tetranychus mcdanieli McGregor))的叶螨和茶红叶螨,细须螨科的扁平螨(例如桔短须螨(Brevipalpus lewisi McGregor)),瘿螨科的尘螨和芽螨和其他食叶螨及危害人类和动物健康的重要的螨类,即麦皮螨科的尘螨,脂螨科的腺囊螨,食甜螨科的谷螨,硬蜱科的羊虱(例如鹿硬蜱(Ixodes scapularis Say)、金环硬蜱(Ixodesholocyclus Neumann)、美洲大蜱(Dermacentor variabilis Say)、美洲花蜱(Amblyomma americanum Linnaeus)),和痒螨科、蒲螨科和疥螨科的痂螨和痒螨;直翅目的成虫和若虫,包括蚱蜢、飞蝗和蟋蟀(例如迁徙蚱蜢(例如迁徙蚱蜢Melanoplus sanguinipesFbricius,长额负蝗M.differentialis Thomas)、美洲蚱蜢(例如Schistocerca americana Drury)、沙漠蝗(Schistocercagregaria Forskal)、飞蝗(Locusta migratoria Linnaeus)、家蟋蟀(Acheta domesticus Linnaeus)、蝼蛄(Gryllotalpas pp.));双翅目的成虫和幼虫,包括潜叶蝇、摇蚊、实蝇(实蝇科)、麦杆蝇(例如瑞典麦杆蝇(Oscinella frit Linnaeus)、土蛆、家蝇(例如Musca domestica Linnaeus)、黄腹厩蝇(例如Fannia canicularisLinnaeus、F.femoralis Stein)、厩蝇(例如Stomoxys calcitransLinnaeus)、秋家蝇、角蝇、飞蝇(例如金蝇属、黑丽蝇属),和其他蝇类害虫,虻(例如虻属)、狂蝇(例如胃蝇属、狂蝇属)、皮蝇(例如皮蝇属)、斑虻(例如斑虻属)、羊虱蝇(例如绵羊虱蝇)和其他短角亚目害虫,蚊虫(例如伊蚊属、按蚊属、库蚊属)、黑蚊(例如原蚋属、蚋属),蠓、蚋、尖眼蚊和其他长角亚目的害虫;缨翅目的成虫和若虫,包括棉蓟马(Thrips tabaci Lindeman)和其他食叶牧草虫;膜翅目的害虫,包括蚂蚁(例如锈色大墨蚁(Camponotusferrugineus Fabricius)、黑木工蚁(Camponotus pennsylvanicusDeGeer)、小家蚁(Monomorium pharaonis Linnaeus)、小火蚁(Wasmannia auropunctata Roger)、火蚁(Solenopsis geminataFabricius)、红外来火蚁(Solenopsis invicta Buren)、阿根廷蚁(Iridomyrmex humilis Mayr)、家褐蚁(Paratrechina longicornisLatreille)、草地蚁(Tetramorium caespitum Linnaeus)、玉米田蚁(Lasius alienus Frster)、臭家蚁(Tapinoma sessile Say)、蜂类(包括木蜂)、大黄蜂、小黄蜂和黄蜂;等翅目的害虫,包括黄胸散白蚁(Reticulitermes flavipes Kollar)、西犀白蚁(Reticulitermes hesperus Banks)、家白蚁(Coptotermesformosanus Shiraki)、西印度干木白蚁(Incisitermes immigransSnyder)和其他经济重要的白蚁;弹尾目害虫,例如西洋衣鱼(Lepismasaccharina Linnaeus)和家衣鱼(Thermobia domestica Packard);食毛目的害虫,包括头虱(Pediculus humanus capitis De Geer)、体虱(Pediculus humanus humanus Linnaeus)、雏鸡羽虱(Menacanthus stramineus Nitszch)、狗羽虱(Trichodectes canisDe Geer)、鸡姬虱(Goniocotes gallinae De Geer)、羽虱(Bovicolaovis Schrank)、阔胸血虱(Haematopinus eurysternus Nitszch)、牛颚虱(Linognathus vituli Linnaeus)和其他危害人类和动物的刺吸和咀嚼的寄生虱类;蚤目的害虫,包括东方鼠蚤(Xenopsyllacheopis Rothschild)、猫栉头蚤(Ctenocephalides felis Bouche)、狗栉头蚤(Ctenocephalides canis Curtis)、禽蚤(Ceratophyllusgallinae Schrank)、禽冠蚤(Echidnophaga gallinacea Westwood)、人蚤(Pulex irritans Linnaeus)和其他侵害哺乳动物和鸟类的跳蚤。另外的节肢动物害虫包括:蜘蛛目的蜘蛛,例如褐皮花蛛(Loxosceles reclusa Gertsch & Mulaik)和黑寡妇球腹蛛(Latrodectus mactans Fabricius),和蚰蜒形目的蜈蚣,例如家蚰蜒(Scutigera coleoptrata Linnaeus)。本发明化合物对以下害虫也有活性,包括线虫纲、多节绦虫亚纲、吸虫纲和棘头(虫)纲的害虫,包括圆线虫亚目、蛔虫目、尖尾亚目、小杆目、旋尾目和嘴刺目经济重要的害虫,例如不局限于经济重要的农业害虫(即根结线虫属的根结线虫、草地垫刃线虫属的草地垫刃线虫、鬃根线虫属的鬃根线虫等)、和危害动物和人类健康的害虫(即所有经济重要的吸虫、绦虫和线虫,如寄生于马的寻常圆线虫、寄生于狗的弓蛔虫、寄生于绵羊的血矛线虫、寄生于狗的恶丝虫、寄生于马的裸头绦虫、寄生于反刍动物的肝片吸虫等)。
本发明的化合物对下述害虫表现出特别高的活性,鳞翅目(例如Alabama argillacea Hübner(棉叶波纹夜蛾)、Archips argyrospilaWalker(美云杉黄卷蛾)、A.rosana Linnaeus(玫瑰黄卷蛾)和其他的黄卷蛾,Chilo suppressalis Walker(二化螟)、Cnaphalocrosismedinalis Guenee(稻纵卷叶蛾)、Crambus caliginosellus Clemens(玉米根草螟)、Crambus teterrellus Zincken(早熟禾草螟)、Cydia pomonella Linnaeus(苹蠹蛾)、Earias insulana Boisduval(棉斑实蛾)、Earias vittella Fabricius(鼎点金刚钻)、Helicverpaarmigera Hübner(美洲棉铃虫)、Helicverpa zea Boddie(棉铃虫)、Heliothis virescens Fabricius(烟夜蛾)、Herpetogrammalicarsisalis Walker(瘤蛾)、Lobesia botrana Denis&Schiffermüller(葡萄小卷蛾)、Pectinophora gossypiellaSaunders(棉红铃虫)、Phyllocnistis citrella Stainton(桔叶潜叶蛾)、Pieris brassicae Linnaeus(大菜粉蝶)、Pieris rapaeLinnaeus(菜粉蝶)、Plutella xylostella Linnaeus(小菜蛾)、Spodoptera exigua Hübner(甜菜夜蛾)、Spodoptera lituraFabricius(斜纹夜蛾)、Spodoptera frugiperda J.E.Smith(草地粘虫)、Trichoplusia ni Hübner(粉纹夜蛾)和Tuta absolutaMeyrick(tomato leafminer))。本发明化合物也对同翅目下述害虫具有经济重要的活性,包括Acyrthisiphon pisum Harris(豌蚜)、Aphis craccivora Koch(豆蚜)、Aphis fabae Scopoli(甜菜蚜)、Aphis gossypii Glover(棉蚜)、Aphis pomi De Geer(苹果蚜)、Aphis spiraecola Patch(绣线菊蚜)、Aulacorthum solaniKaltenbach(茄沟无网蚜)、Chaetosiphon fragaefolii Cockerell(草莓中瘤钉毛蚜)、Diuraphis noxia Kurdjumov/Mordvilko(俄罗斯麦蚜)、Dysaphis plantaginea Paaserini(苹粉红劣蚜)、Eriosoma lanigerum Hausmann(苹果绵蚜)、Hyalopterus pruniGeoffroy(桃粉大尾蚜)、Lipaphis erysimi Kaltebach(菜缢管蚜)、Metopolophium dirrhodum Walker(蔷薇麦蚜)、Macrosiphumeuphorbiae Thomas(马铃薯长管蚜)、Myzus persicae Sulzer(桃蚜)、Nasonovia ribisnigri Mosley(莴苣蚜)、Pemphigus spp.(根蚜和瘤蚜)、Rhopalosiphum maidis Fitch(玉米蚜)、Rhopalosiphum padi Linnaeus(粟缢管蚜)、Schizaphis graminumRondani(草间裂蚜茧蜂)、Sitobion avenae Faricius(英国谷蚜)、Therioaphis maculata Buckton(苜蓿斑蚜)、Toxoptera aurantiiBoyer de Fonscolombe(茶二叉蚜)和Toxoptera citricida Kirkaldy(桔二叉蚜);Adelges spp.(球蚜属);Phylloxera devastatrixPergande(美核桃根瘤蚜);Bemisia tabaci Gennadius(棉粉虱)、Bemisiaargentifolii Bellows & Perring(银叶粉虱)、Dialeurodescitri Ashmead(柑桔粉虱)和Trialeurodes vaporariorum Westwood(温室白粉虱);Empoasca fabae Harris(蛋豆微叶蝉)、Laodelphaxstriatellus Fallen(稻灰飞虱)、Macrolestes quadrilineatusForbes(六点叶蝉)、Nephotettix cinticeps Uhler(黑尾叶蝉)、Nephotettixnigropictus Stl(稻叶蝉)、Nilaparvata lugens Stl(稻褐飞虱)、Peregrinus maidis Ashmead(玉米蜡蝉)、Sogatellafurcifera Horvath(白背稻虱)、Sogatodes orizicola Muir(稻飞虱)、Typhlocyba pomaria McAtee(草白小叶蝉)、Erythroneuraspp.(红斑叶蝉);Magicidadaseptendecim Linnaeus(十七年蝉);Icerya purchasi Maskell(吹绵蚧)、Quadraspidiotus perniciosusComstock(梨笠圆盾蚧);Planococcus citri Risso(桔粉蚧);Pseudococcus spp.(其他的粉蚧类群);Cacopsylla pyricolaFoerster(梨叶虱)、Trioza diospyri Ashmead(柿木虱)。上述化合物也对下述的半翅目害虫有活性,包括Acrosternum hilare Say(喜绿蝽)、Anasa tristis De Geer(南瓜缘蝽)、Blissus leucopterusleucopterus Say(玉米长蝽)、Corythuca gossypii Fabricius(棉网蝽)、Cyrtopeltis modesta Distant(番茄盲蝽)、Dysdercussuturellus Herrich-Schffer(棉黑翅红蝽)、Euchistus servusSay(褐臭椿)、Euchistus variolarius Palisot de Beauvoi(一点臭蝽)、Graptosthetus spp.(实蝽)、Leptoglossus corculusSay(松子喙缘蝽)、Lygus lineo laris Palisot de Beauvois(牧草盲蝽)、Nezara viridula Linnaeus(稻绿蝽)、Oebalus pugnaxFabricius(稻臭蝽)、Oncopeltus fasciatus Dallas(大马利筋长蝽)、Pseudatomoscelisseriatus Reuter(棉跳盲蝽)。通过本发明化合物防治的其他目的害虫包括缨翅目(例如Frankliniellaoccidentalis Pergande(苜蓿蓟马)、Scirthothrips citri Moulton(桔实蓟马)、Sericothripsvariabilis Beach(黄豆蓟马)和Thripstabaci Lindeman(棉蓟马));和鞘翅目(例如Leptinotarsadecemlineata Say(马铃薯甲虫)、Epilachna varivestis Mulsant(墨西哥豆瓢虫)和叩甲属、叩甲(Athous)或草金针虫属的切根虫)。
本发明化合物可与一种或多种另外的生物活性化合物或制剂包括杀虫剂、杀菌剂、杀线虫剂、杀细菌剂、杀螨剂、生长调节剂如促生根剂、化学不育剂、化学信息素、驱避剂、引诱剂、信息素、促食剂、其他的生物活性化合物或昆虫病原细菌、病毒或真菌混合,形成多组分杀虫剂,以得到更广谱的农业应用。因此,本发明组合物可再包含生物有效量的至少一种另外的生物活性化合物或制剂。可用于与本发明化合物进行加工的上述生物活性化合物或制剂的实例是:杀虫剂如爱福丁、乙酰甲胺磷、啶虫脒、阿维菌素、艾扎丁、谷硫磷、氟氯菊酯、联苯肼酯、噻嗪酮、呋喃丹、虫螨腈、氟啶脲、毒死蜱、甲基毒死蜱、环虫酰肼、噻虫胺、氟氯氰菊酯、高效氟氯氰菊酯、氯氟氰菊酯、高效氯氟氰菊酯、氯氰菊酯、灭蝇胺、溴氰菊酯、丁醚脲、二嗪磷、除虫脲、乐果、苯虫醚、甲胺基阿维菌素,硫丹、高效氰戊菊酯、乙硫虫腈、苯硫威、苯氧威、甲氰菊酯、唑螨酯、氰戊菊酯、氟虫腈、flonicamid、氟氰戊菊酯、氟胺氰菊酯、氟虫脲、地虫磷、特丁苯酰肼、氟铃脲、吡虫啉、二唑虫、丙胺磷、虱螨脲、马拉硫磷、蜗牛敌、甲胺磷、杀扑磷、灭多威、烯虫酯、甲氧滴滴涕、久效磷、甲氧苯酰肼、硝虫噻嗪、双苯氟脲、甲氨叉威、对硫磷、甲基对硫磷、氯菊酯、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、抗蚜威、丙溴磷、拒嗪酮、啶虫丙醚、蚊蝇醚、鱼藤酮、多杀菌素、乙丙硫磷、双苯酰肼、伏虫隆、七氟菊酯、特丁磷、杀虫畏、噻虫啉、噻虫嗪、硫双灭多威、杀虫双、四溴菊酯、敌百虫和杀虫隆;杀菌剂如噻二唑素、腈嘧菊酯、苯菌灵、灭瘟素、波尔多液(三价铜硫酸盐)、糠菌唑、氯环丙酰胺、敌菌丹、克菌丹、多菌灵、地茂散、百菌清、氯氧化铜、铜盐、cyflufenamid、清菌脲、环唑醇、环丙嘧啶、(S)-3,5-二氯-N-(3-氯-1-乙基-1-甲基-2-氧代丙基)-4-甲基苯甲酰胺(RH7281)、双氯氰菌胺(S-2900)、哒菌清、氯硝胺、醚唑、(S)-3,5-二氢-5-甲基-2-(甲硫基)-5-苯基-3-(苯氨基)-4H-咪唑-4-酮(RP407213)、烯酰吗啉、醚菌胺、烯唑醇、烯唑醇-M、多果定、克瘟散、氧唑菌、唑酮菌、咪唑菌酮、异嘧菌醇、腈苯唑、异丙菌胺(fencaramid)(SZX0722)、拌种咯、苯锈啶、丁苯吗啉、薯瘟锡、毒菌锡、氟啶胺、氟菌、氟联苯菌(RPA403397)、喹唑菌酮、氟硅唑、氟酰胺、粉唑醇、灭菌丹、乙磷铝、氟氨丙灵、呋吡唑灵(S-82658)、己唑醇、环戊唑醇、异稻瘟净、异丙定、稻瘟灵、春雷霉素、亚胺菌、代森锰锌、代森锰、mefenoxam、灭氧灭锈胺、甲霜灵、叶菌唑、叉氨苯酰胺(SSF-126)、腈菌唑、田安甲砷铁(甲基砷酸铁)、霜灵、戊菌唑、戊菌隆、噻菌灵、丙氯灵、百维灵、丙环唑、啶斑肟、唑菌胺酯、二甲嘧菌胺、咯喹酮、喹氧灵、螺茂胺、硫、戊唑醇、氟醚唑、涕必灵、溴氟唑菌、甲基托布津、福美双、噻酰菌胺、三唑酮、唑菌醇、三环唑、肟菌酯、戊叉唑菌、有效霉素和烯菌酮;杀线虫剂如涕灭威、甲氨叉威、克线磷;杀细菌剂如链霉素;杀螨剂如杀螨脒、杀螨猛、乙酯杀螨醇、三环锡、开乐散、除螨灵、特苯唑、喹螨醚、杀螨锡、甲氰菊酯、唑螨酯、噻螨酮、克螨特、哒螨酮和吡螨胺;和生物制剂如苏云金杆菌包括鲇泽亚种和库斯塔克亚种、苏云金杆菌δ毒素、杆状病毒和昆虫致病细菌、病毒和真菌。本发明的化合物及其组合物可施用到遗传改造表达对无脊椎害虫有毒性(如苏云金杆菌毒素)的蛋白的植物上。外用无脊椎害虫防治化合物和组合物的效果可与所表达的毒性蛋白起协同作用。
上述农业保护剂一般参考The Pesticide Manual,12th Edition,C.D.S.Tomlin,Ed.,British Crop Protection Council,Farnham,Surrey,U.K.,2000。
与本发明化合物混合的优选的杀虫剂和杀螨剂包括拟除虫菊酯类如氯氰菊酯、氯氟氰菊酯、氟氯氰菊酯和β-氟氯氰菊酯、高氰戊菊酯、氰戊菊酯和四溴菊酯;氨基甲酸酯类如苯硫威、灭多威、甲氨叉威和硫双灭多威;新烟碱类如噻虫胺、吡虫啉和噻虫啉;神经钠通道阻断剂如二唑虫;杀虫的大环内酯如多杀菌素、爱福丁、阿维菌素和甲胺基阿维菌素;γ-氨基丁酸(GABA)拮抗剂如硫丹、乙硫虫腈和氟虫腈;杀虫脲类如氟虫脲和杀虫隆;保幼激素模拟物如茂醚和蚊蝇醚;拒嗪酮;和虫螨脒。与本发明化合物混合的优选的生物制剂包括苏云金杆菌和苏云金杆菌δ毒素,以及自然发生或经遗传改造的包括杆状病毒科成员的病毒杀虫剂和食虫真菌。
最优选的混合物包括本发明化合物与氯氟氰菊酯的混合物;本发明化合物与β-氟氯氰菊酯的混合物;本发明化合物与高氰戊菊酯的混合物;本发明化合物与灭多威的混合物;本发明化合物与吡虫啉的混合物;本发明化合物与噻虫啉的混合物;本发明化合物与二唑虫的混合物;本发明化合物与爱福丁的混合物;本发明化合物与硫丹的混合物;本发明化合物与乙硫虫腈的混合物;本发明化合物与氟虫腈的混合物;本发明化合物与氟虫脲的混合物;本发明化合物与蚊蝇醚的混合物;本发明化合物与拒嗪酮的混合物;本发明化合物与虫螨醚的混合物;本发明化合物与苏云金杆菌的混合物和本发明化合物与苏云金杆菌δ毒素的混合物。
在某些情况下,与具有相似防治谱但作用方式不同的其他无脊椎害虫防治化合物或制剂组合特别有利于控制抗性。因此,本发明组合物可再包含生物有效量的具有相似防治谱但作用方式不同的至少一种另外的无脊椎害虫防治化合物或制剂。用生物有效量的本发明化合物接触经遗传改造表达出植物保护化合物(例如蛋白质)的植物或植物的场所,也可得到更宽的植物保护谱,有利于抗性的控制。
通过向害虫的环境包括包括农业和/或非农业的侵染场所,所要保护的区域,或直接在所要防治的害虫上,以有效量使用一种或多种本发明的化合物,可在农业和非农业应用中防治无脊椎害虫。因此,本发明还包括在农业和/或非农业应用中防治无脊椎害虫的方法,包括用生物有效量的一种或多种本发明化合物,或用生物有效量的含有至少一种上述化合物的组合物,或用包含至少一种上述化合物和生物有效量的至少一种另外的生物活性化合物或制剂的组合物接触无脊椎害虫或其环境。包含本发明化合物和有效量的至少一种另外的生物活性化合物或制剂的适合的组合物的实例包括颗粒组合物,其中,另外的生物活性化合物以与本发明化合物相同的颗粒剂形式存在,或以与本发明化合物存在的颗粒剂分开的颗粒剂的形式存在。
优选的接触方法是喷雾。有选择性地,含有本发明化合物的颗粒组合物可施用到植物叶片或土壤中。本发明化合物通过植物吸收传导也是有效的,用含有本发明化合物的组合物以液剂土壤浸湿、颗粒剂施到土壤,育苗箱处理或移栽浸渍的使用来接触植物。化合物通过将含有本发明化合物的组合物局部施用到侵染场所也是有效的。其他的接触方法包括通过直接或滞留喷雾、飞机喷洒、凝胶、种子包衣、微胶囊化、内吸摄入、饵剂、耳标、丸剂、烟雾、熏蒸剂、气雾剂、粉剂等施用本发明化合物或组合物。本发明化合物也可浸渍到制作无脊椎害虫防治设备(例如昆虫网)的材料中。
本发明的化合物可以加入到无脊椎害虫食用的饵料组合物中或在例如诱捕器、饵料站(bait station)等的设备中使用。上述的饵料组合物可以是颗粒组合物的形式,含有(a)活性成分,即通式I化合物、N-氧化物、或其盐,(b)一种或多种食物原料,(c)任选的引诱剂,和(d)任选的一种或多种湿润剂。重要的是含有约0.001-5%活性成分;约40-99%食物原料和/或引诱剂;和任选的约0.05-10%的湿润剂的颗粒剂或饵料组合物;在非常低的施用量防治土壤无脊椎害虫是有效的,特别是通过摄食而不是直接接触致命的活性成分的剂量。重要的一些食物原料具有食物源和引诱剂的双重功能。食物原料包括糖类、蛋白质和脂类。食物原料的实例是植物粉、食糖、淀粉、动物脂肪、植物油、酵母抽提物和牛奶固形物。引诱剂的实例是添味剂和食用香料,如水果和植物抽提物、香料、或其他的动物和植物组分,信息素或其他已知的引诱目标无脊椎害虫的制剂。湿润剂,即湿度保持剂的实例是乙二醇和其他的多元醇、甘油和山梨糖醇。重要的是用于防治无脊椎害虫包括单独防治或与蚂蚁、白蚁和蟑螂结合防治的饵料组合物(和利用上述饵料组合物的方法)。防治无脊椎害虫的设备可包含本发明的饵料组合物和适于放置该饵料组合物的外壳,其中外壳具有至少一个开口,其大小允许无脊椎害虫通过该开口,使得无脊椎害虫从外壳外的位置能够有机会得到饵料组合物,其中外壳也适于放置在无脊椎害虫可能的或已知的活动场所内或附近。
本发明化合物可以它们的纯体形式使用,但最经常使用的是含有一种或多种化合物与适当的载体、稀释剂和表面活性剂的制剂,根据预期的最终用途,还可与食物结合使用。优选的施用方法包括喷洒化合物的水分散液或精炼油溶液。与喷雾油、喷雾油浓缩物、展着增稠剂、助剂、其他溶剂和增效剂如胡椒基丁醚组合使用,常常可提高化合物的防效。对于非农业应用来说,上述喷雾可由喷雾容器如罐、瓶或其他容器来进行,或通过泵或由加压的容器,如加压的气体喷雾罐来释放。上述喷雾组合物可采取多种形式,例如,喷雾、薄雾、泡沫、烟或烟雾。视情况而定,上述的喷雾组合物可再包含推进剂、发泡剂等。重要的是包含本发明化合物或组合物和推进剂的喷雾组合物。有代表性的推进剂包括,但不局限于甲烷、乙烷、丙烷、异丙烷、丁烷、异丁烷、丁烯、戊烷、异戊烷、新戊烷、戊烯、含氢氟代烃(hydrofluorocarbon)、全卤代氟氯烃(chlorofluoroacarbon)、甲醚、以及上述推进剂的混合物。重要的是用于防治无脊椎害虫包括单独防治或与蚊子、黑蚊、厩蝇、斑虻、虻、黄蜂、小黄蜂、大黄蜂、扁虱、蜘蛛、蚂蚁、蚋等结合防治的喷雾组合物(和利用上述喷雾组合物由喷雾容器中分散的方法)。
有效防治所需的施药率(即“生物有效量”)取决于以下因素:所防治的无脊椎害虫的种类、害虫的生活史、生长期、大小、地点、时期、寄主植物或动物、取食行为、交配行为、环境湿度、温度等。在正常环境下,每公顷大约0.01-2kg有效成分的施用率足以防治农业生态系中的害虫,但少至0.0001kg/ha可能是足够的,或者可能需要多至8kg/ha。对于非农业应用,有效施用率是大约1.0-50mg/m2,但少至0.1mg/m2可能是足够的,或者可能需要多至150mg/m2。本领域技术人员可轻易的确定达到所要的无脊椎害虫防治水平所需的生物有效量。
下面的试验证明了本发明化合物对具体害虫的防治效能。“防治效能”代表抑制节肢动物生长(包括死亡),使得取食明显减少。但是,由该化合物得到的害虫防治保护并不限制于这些品种。关于化合物的描述见索引表A。索引表中的缩写“Me”是甲基。缩写“Ex.”代表“实施例”,后面的数字表示在该实施例中制备该化合物。
索引表A
化合物 | R1a | R1b | R13 | R17 | m | m.p.℃ |
1(Ex.1)23456 | MeClMeMeMeMe | ClClCNIClCl | BrBrCF3BrCF3OCH2CF3 | ClClClClClCl | 000000 | 151-153171-172202-203161-162152-153151-152 |
发明的生物实施例
试验A
为了评价对小菜蛾(Plutella xylostella)防治,试验单元包括一小开口的容器,里面放有生长12-14天的萝卜植株。用一片昆虫食料上的10-15头新生幼虫进行预侵染,通过取样器从一片硬化了生长有许多幼虫的昆虫食料上取出一团块(plug),并将含有昆虫和食料的团块转移到试验单元中。随着食料团块变干,幼虫移向试验植株。
除非另外说明,试验化合物用含有10%丙酮、90%水和300ppm的含有烷基芳基聚氧乙烯、游离脂肪酸、乙二醇和异丙醇的X-77Spreader Lo-Foam Formula非离子表面活性剂(LovelandIndustries,Inc.Greeley,Colorado,USA)的溶液进行加工。用定位在每个试验单元顶部1.27cm(0.5英寸)处的1/8JJ通体(custombody)(Spraying Systems Co.Wheaton,Illinois,USA)通过SUJ2喷雾嘴以1mL液体的量施用加工好的化合物。实验化合物2、3、4、5和6以10ppm的浓度进行喷雾,实验化合物1以50ppm的浓度进行喷雾,所有的实验化合物重复三次。喷完加工好的试验化合物后,每个试验单元风干1小时,然后上面覆盖一黑色带筛孔的盖子。试验单元在25℃,相对湿度70%的生长室内放置6天。然后基于所取食的叶片目测植株被取食损坏的程度。
供试的化合物中,下面化合物获得了非常好至良好的植物保护水平(20%或更少受到取食损坏):1、2、3、4、5和6。
试验B
为了评价对草地粘虫(Spodoptera frugiperda)的防治,试验单元包括具有一小开口的容器,里面放有生长4-5天的玉米(maize)植株。用一片害虫食料上的10-15头1天大的幼虫进行预侵染(用取样器)。
如实验A所描述,实验化合物2、3、4、5和6进行加工并在10ppm进行喷雾,实验化合物1进行加工并在50ppm进行喷雾。该操作重复三次。喷完后,试验单元放置在生长室内,然后,按照试验A所描述目测侵染率。
供试的化合物中,下面化合物得到了良好的植物保护水平(20%或更少受到取食损坏):1、2、3、4、5和6。
Claims (13)
2.权利要求1的化合物,其中
R1基团中的一个在2-位上与苯环相连;
R4、R5、R6和R7每个独立地是Me;
R8和R9是H;
R10、R11和R12是Me;
n是1或2;和
r是1。
3.权利要求2的化合物,其中
每个R1独立地是CH3、CN或卤素。
6.权利要求5的化合物,其中
R6和R7是H。
7.一种防治无脊椎害虫的方法,包括用生物有效量的权利要求1的化合物接触无脊椎害虫或其环境。
8.权利要求7的方法,其中的无脊椎害虫是蟑螂、蚂蚁或白蚁,通过取食含有化合物的饵料组合物来接触化合物。
9.权利要求7的方法,其中的无脊椎害虫是蚊子、黑蚊、厩蝇、斑虻、虻、黄蜂、小黄蜂、大黄蜂、扁虱、蜘蛛、蚂蚁或蚋,通过由喷雾容器中分散出含有化合物的喷雾组合物来接触。
10.一种防治无脊椎害虫的组合物,包含生物有效量的权利要求1的化合物和至少一种另外的选自表面活性剂、固体稀释剂和液体稀释剂的组分。
11.一种喷雾组合物,包含:
(a)权利要求1的化合物;和
(b)推进剂。
12.一种饵料组合物,包含:
(a)权利要求1的化合物;
(b)一种或多种食物原料;
(c)任选的引诱剂;和
(d)任选的湿润剂。
13.一种防治无脊椎害虫的设备,包括:
(a)权利要求12的饵料组合物;和
(b)适于放置该饵料组合物的外壳,其中外壳具有至少一个开口,其大小允许无脊椎害虫通过该开口,使得无脊椎害虫从外壳外的位置能够有机会得到饵料组合物,其中外壳也适于放置在无脊椎害虫可能的或已知的活动场所内或附近。
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WO2002062807A1 (de) * | 2001-02-06 | 2002-08-15 | Bayer Cropscience Ag | Phthalsäurediamide, ein verfahren zu ihrer herstellung und ihre verwendung als schädlingsbekämpfungsmittel |
-
2003
- 2003-10-01 MX MXPA05003337A patent/MXPA05003337A/es not_active Application Discontinuation
- 2003-10-01 AU AU2003282711A patent/AU2003282711A1/en not_active Abandoned
- 2003-10-01 EP EP03774596A patent/EP1546160A1/en not_active Withdrawn
- 2003-10-01 US US10/527,863 patent/US7211270B2/en not_active Expired - Fee Related
- 2003-10-01 BR BR0314497-6A patent/BR0314497A/pt not_active IP Right Cessation
- 2003-10-01 KR KR1020057005681A patent/KR20050049512A/ko not_active Application Discontinuation
- 2003-10-01 JP JP2004543434A patent/JP2006502226A/ja not_active Withdrawn
- 2003-10-01 WO PCT/US2003/031677 patent/WO2004033468A1/en not_active Application Discontinuation
- 2003-10-01 CN CNB2003801008458A patent/CN100349901C/zh not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001070671A2 (en) * | 2000-03-22 | 2001-09-27 | E.I. Du Pont De Nemours And Company | Insecticidal anthranilamides |
WO2002062807A1 (de) * | 2001-02-06 | 2002-08-15 | Bayer Cropscience Ag | Phthalsäurediamide, ein verfahren zu ihrer herstellung und ihre verwendung als schädlingsbekämpfungsmittel |
Also Published As
Publication number | Publication date |
---|---|
US20060052343A1 (en) | 2006-03-09 |
AU2003282711A1 (en) | 2004-05-04 |
MXPA05003337A (es) | 2005-07-05 |
JP2006502226A (ja) | 2006-01-19 |
KR20050049512A (ko) | 2005-05-25 |
WO2004033468A1 (en) | 2004-04-22 |
US7211270B2 (en) | 2007-05-01 |
BR0314497A (pt) | 2005-08-02 |
EP1546160A1 (en) | 2005-06-29 |
CN1703417A (zh) | 2005-11-30 |
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