CN1829707A - 氰基邻氨基苯甲酰胺杀虫剂 - Google Patents
氰基邻氨基苯甲酰胺杀虫剂 Download PDFInfo
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- CN1829707A CN1829707A CNA2004800029911A CN200480002991A CN1829707A CN 1829707 A CN1829707 A CN 1829707A CN A2004800029911 A CNA2004800029911 A CN A2004800029911A CN 200480002991 A CN200480002991 A CN 200480002991A CN 1829707 A CN1829707 A CN 1829707A
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- MXMXHPPIGKYTAR-UHFFFAOYSA-N silthiofam Chemical compound CC=1SC([Si](C)(C)C)=C(C(=O)NCC=C)C=1C MXMXHPPIGKYTAR-UHFFFAOYSA-N 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
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- 239000012312 sodium hydride Substances 0.000 description 1
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- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
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- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
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- 239000003765 sweetening agent Substances 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- VJQYLJSMBWXGDV-UHFFFAOYSA-N tiadinil Chemical compound N1=NSC(C(=O)NC=2C=C(Cl)C(C)=CC=2)=C1C VJQYLJSMBWXGDV-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
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- 229940005605 valeric acid Drugs 0.000 description 1
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- A—HUMAN NECESSITIES
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- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
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- A—HUMAN NECESSITIES
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- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing acyclic or cycloaliphatic radicals
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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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
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- A—HUMAN NECESSITIES
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- A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
本发明提供式(I)的化合物、其N-氧化物和适宜的盐,其中R1为Me、Cl、Br或F;R2为F、Cl、Br、C1-C4卤烷基或C1-C4卤烷氧基;R3为F、Cl或Br;R4为H或C1-C4烷基、C3-C4链烯基、C3-C4炔基、C3-C5环烷基或C4-C6环烷基烷基,它们各自任选被选自下组的一个取代基取代:卤素、CN、SMe、S(O)Me、S(O) 2Me和OMe;R5为H或Me;R6为H、F或Cl;R7为H、F或Cl。本发明还公开了用于防治无脊椎动物害虫的方法,其包括使该无脊椎动物害虫或其环境与生物学有效量的式(I)的化合物、其N-氧化物或该化合物的适宜的盐(例如作为本文所述的组合物)接触。本发明还涉及用于防治无脊椎动物害虫的组合物,其包含生物学有效量的式(I)的化合物、其N-氧化物或该化合物的适宜的盐,以及至少一种选自表面活性剂、固体稀释剂和液体稀释剂的附加组分。
Description
技术领域
本发明涉及适于农学和非农学用途,包括以下所列的那些用途的某些邻氨基苯甲酰胺、其N-氧化物、盐和组合物,以及使用它们在农学和非农学环境中防治无脊椎动物害虫的方法。
背景技术
无脊椎动物害虫的防治在实现高种植效率中极为重要。无脊椎动物害虫对生长和贮存的农作物的损害会引起生产率的显著降低,并因此导致消费者的花费增加。在林业、温室作物、观赏植物、苗圃作物、贮藏食物和纤维产品、家畜、家用品(household)和公众和动物健康中的无脊椎动物害虫防治也是重要的。用于这些目的的许多产品是可商购的,但是仍然需要更有效、低成本、低毒性、对环境安全或具有不同作用方式的新化合物。
WO 01/070671公开了式i的N-酰基邻氨基苯甲酸衍生物作为杀节肢动物剂:
其中,A和B独立地为O或S;J是任选被取代的苯环、5-或6-员杂芳环、萘基环系统或芳族8-、9-或10-员稠合杂双环系统;R1和R3独立地为H或任选被取代的C1-C6烷基;R2是H或C1-C6烷基;每个R4独立地为H、C1-C6烷基、C1-C6卤烷基、卤素或CN;并且n为1至4。
发明内容
本发明涉及式I的化合物、其N-氧化物或其盐,
其中
R1为Me、Cl、Br或F;
R2为F、Cl、Br、C1-C4卤烷基或C1-C4卤烷氧基;
R3为F、Cl或Br;
R4为H;C1-C4烷基、C3-C4链烯基、C3-C4炔基、C3-C5环烷基或C4-C6环烷基烷基,它们各自任选被选自下组的一个取代基取代:卤素、CN、SMe、S(O)Me、S(O)2Me和OMe;
R5为H或Me;
R6为H、F或Cl;且
R7为H、F或Cl。
本发明还涉及用于防治无脊椎动物害虫的组合物,其包含生物学有效量的式I的化合物和至少一种选自表面活性剂、固体稀释剂和液体稀释剂的附加组分,以及任选的有效量的至少一种附加生物学活性化合物或活性剂。
本发明还涉及用于防治无脊椎动物害虫的方法,其包括使该无脊椎动物害虫或其环境与生物学有效量的式I的化合物(如作为本文所述的组合物)接触。本发明还涉及用于防治无脊椎动物害虫的方法,其包括使该无脊椎动物害虫或其环境与生物学有效量的组合物接触,所述组合物包含生物学有效量的式I的化合物和至少一种选自表面活性剂、固体稀释剂和液体稀释剂的附加组分,所述组合物任选进一步包含有效量的至少一种附加生物学活性化合物或活性剂。
本发明进一步涉及喷雾组合物,其包含式I的化合物和抛射剂,本发明还涉及饵料组合物,其包含式I的化合物、一种或多种食物材料、任选的诱虫剂和任选的湿润剂。本发明还涉及用于防治无脊椎动物害虫的装置,其包含所述饵料组合物和适于接收该饵料组合物的外壳,其中该外壳具有至少一个开孔,其大小允许该无脊椎动物害虫通过该开孔,使该无脊椎动物害虫可以从该外壳以外的位置接近该饵料组合物,并且其中该外壳进一步适于放在该无脊椎动物害虫可能或已知的活动场所中或附近。
具体实施方式
在以上叙述中,单独使用或者在复合词,如“烷硫基”或“卤烷基”中使用的术语“烷基”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异构体。单独使用或者在复合词,如“卤烷氧基”中使用的术语“卤素”包括氟、氯、溴或碘。此外,当用于复合词,如“卤烷基”或“卤烷氧基”中时,所述烷基或烷氧基可以部分或全部被可以相同或不同的卤原子取代。“卤烷基”的实例包括F3C、ClCH2、CF3CH2和CF3CCl2。“卤烷氧基”的实例包括CF3O、HCF2O、CCl3CH2O、HCF2CH2CH2O和CF3CH2O。
本领域技术人员会理解,因为氮需要存在孤对电子来氧化成氧化物,所以不是所有含氮杂环都可以形成N-氧化物;本领域技术人员会了解能够形成N-氧化物的那些含氮杂环。本领域技术人员还会理解,叔胺可以形成N-氧化物。用于制备杂环和叔胺的N-氧化物的合成方法对于本领域技术人员是非常熟知的,包括用诸如过乙酸和间氯过苯甲酸(MCPBA)的过氧酸、过氧化氢、诸如叔丁基氢过氧化物的烷基氢过氧化物、过硼酸钠和诸如二甲基二环氧乙烷(dimethydioxirane)的二环氧乙烷来氧化杂环和叔胺。这些用于制备N-氧化物的方法已经在文献中得到了详细的描述和综述,举例来说参阅:T.L.Gilchrist in Comprehensive Organic Synthesis,Vol.7,pp748-750,S.V.Ley,Ed.,Pergamon Press;M.Tisler和B.Stanovnik inComprehensive Heterocyclic Chemistry,vol.3,pp 18-20,A.J.Boulton和A.McKillop,Eds.,Pergamon Press;M.R.Grimmett和B.R.T.Keenein Advances in Heterocyclic Chemistry,vol.43,pp 149-161,A.R.Katritzky,Ed.,Academic Press;M.Tisler和B.Stanovnik in Advancesin Heterocyclic Chemistry,vol.9,pp 285-291,A.R.Katritzky和A.J.Boulton,Eds.,Academic Press;以及G.W.H.Cheeseman和E.S.G.Werstiuk in Advances in Heterocyclic Chemistry,vol.22,pp 390-392,A.R.Katritzky和A.J.Boulton,Eds.,Academic Press。
本发明的化合物可以作为一种或多种立体异构体存在。各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。本领域技术人员会理解,当一种立体异构体相对于其它立体异构体而言浓度大时,或者当其与其它立体异构体分离时,可能更有活性和/或可能表现出有利的作用。另外,本领域技术人员知道如何分离、富集和/或选择性地制备所述立体异构体。因此,本发明包括选自式I、其N-氧化物和盐的化合物。本发明的化合物可以作为立体异构体的混合物、单个立体异构体或者作为旋光形式存在。
本发明的化合物的盐包括与无机或有机酸,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。在本发明的组合物和方法中,本发明的化合物的盐优选适于本文描述的农学和/或非农学用途。
重要的是式I的化合物,其中
R4为H或C1-C4烷基,其任选被选自CN、SMe和OMe的一个取代基取代;
R5为H或Me;
R6为H;且
R7为H。
由于成本、容易合成和/或生物学有效性的原因,优选的化合物是:
优选1.式1的化合物,其中
R1为Me或Cl;
R2为Cl、Br、CF3、OCF2H、OCF3或OCH2CF3;且
R4为H、Me、Et、i-Pr、t-Bu、CH2CN、CH(Me)CH2SMe或C(Me)2CH2SMe。
优选2.优选1的化合物,其中
R2为Cl、Br、CF3或OCH2CF3;
R4为H、Me、Et或i-Pr;且
R5为H。
重要的是优选1和优选2的化合物,其中R6为H;且R7为H。
优选的本发明的组合物为包含以上优选的化合物的组合物。优选的使用方法为涉及以上优选的化合物的方法。
式I的化合物可以通过一种或多种以下如路线1-20所述的方法及变体来制备。除非另有说明,以下式1-24的化合物中R1、R2、R3、R4和R5的定义如以上在发明内容中所定义。
式I的化合物可以通过式2的苯并噁嗪酮与式HNR4R5的胺的反应来制备,如路线1所示。该反应可以以纯物质进行,或者在多种适宜的溶剂中进行,所述溶剂包括四氢呋喃、乙醚、二噁烷、甲苯、二氯甲烷和氯仿,最佳温度为室温至溶剂的回流温度。化学文献中详细报道了苯并噁嗪酮与胺的一般反应生成邻氨基苯甲酰胺。苯并噁嗪酮化学的综述参阅Jakobsen等人,Biorganic and Medicinal Chemistry2000,8,2095-2103,该文献引入本文作参考。还参阅G.M.Coppola,J.Heterocyclic Chemistry 1999,36,563-588。
路线1
式1的化合物还可由式3的卤代邻氨基苯甲酰二胺(haloanthranilic diamide)(其中X为卤素,优选碘或溴)通过路线2所示的偶联方法来制备。任选地在存在或不存在合适的钯催化剂[例如四(三苯基膦)钯(O)或二氯二(三苯基膦)钯(II)]并且任选地在存在或不存在金属卤化物(例如碘化亚铜、碘化锌或碘化钾)的情况下,在合适的溶剂如乙腈、N,N-二甲基甲酰胺或N-甲基吡咯烷酮中,任选在室温到溶剂回流范围内的温度下,式3的化合物和金属氰化物(例如氰化亚铜、氰化锌或氰化钾)反应,获得式1的化合物。当钯催化剂用于偶联反应时,合适的溶剂也可以是四氢呋喃或二噁烷。
路线2
式2的氰基苯并噁嗪酮可通过路线3描述的方法制备。,式4的卤代苯并噁嗪酮(其中X为卤素,优选碘或溴)和金属氰化物用与以上路线2描述相似的偶联方法(任选地存在或不存在钯催化剂并且任选地存在或不存在金属卤化物)反应,获得式2的化合物。
路线3
式2的氰基苯并噁嗪酮也可通过路线4描述的方法经式5的吡唑羧酸和式6的氰基邻氨基苯甲酸偶联来制备。这一反应包括在叔胺如三乙胺或吡啶存在下甲磺酰氯加成至式5的吡唑羧酸,接着进行式6的氰基邻氨基苯甲酸加成,接着进行叔胺和甲磺酰氯的第二次加成。
路线4
路线5描述了式2的苯并噁嗪酮的另一制备方法,其包括式7的靛红酸酐与式8的吡唑酰基氯的偶联。适于该反应的溶剂有如吡啶或吡啶/乙腈。式8的酰基氯可以从式5的相应的酸通过已知方法如亚硫酰二氯或草酰氯氯化获得。
路线5
如路线6中所示,式3的卤代邻氨基苯甲酰二胺可通过其中X为卤素的式4的苯并噁嗪酮和式HNR4R5的胺用与以上路线1相似的方法反应来制备。这一反应的条件与路线1中描述的条件相似。
路线6
如路线7中所示,式4的卤代苯并噁嗪酮(其中X为卤素)可通过式5的吡啶基吡唑羧酸和式9的卤代邻氨基苯甲酸(其中X为卤素)通过与以上路线4描述相似的方法直接偶联来制备。这一反应包括在叔胺如三乙胺或吡啶存在下甲磺酰氯加成至式5的吡唑羧酸,接着进行式9的卤代邻氨基苯甲酸加成,接着进行叔胺和甲磺酰氯的第二次加成。这一方法一般获得良好的苯并恶嗪酮收率。
路线7
如路线8中所示,式4的卤代苯并噁嗪酮也可经式10的靛红酸酐(其中X为卤素)与式8的吡唑酰基氯通过与以上路线5描述相似的方法偶联来制备。
路线8
式6的氰基邻氨基苯甲酸可如路线9所述从卤代邻氨基苯甲酸制备。式9的卤代邻氨基苯甲酸(其中X为卤素)与金属氰化物用与以上路线2所述相同的偶联方法(任选地存在或不存在钯催化剂并且任选地存在或不存在金属卤化物)反应,获得式6的化合物。
路线9
如路线10中所示,式7的氰基靛红酸酐可由式6的氰基邻氨基苯甲酸通过与光气(或光气等价物如三光气)或氯甲酸烷基酯(例如氯甲酸甲酯)在合适溶剂如甲苯或四氢呋喃中反应来制备。
路线10
如路线11中所示,式9的卤代邻氨基苯甲酸可通过式11的未取代的邻氨基苯甲酸和N-氯代琥珀酰亚胺(NCS)、N-溴代琥珀酰亚胺(NBS)或N-碘代琥珀酰亚胺(NIS)在溶剂如N,N-二甲基甲酰胺(DMF)中分别直接卤化,产生式9的相应的卤素取代的酸。
路线11
如路线12中所示,式10的卤代靛红酸酐可从式9的卤代邻氨基苯甲酸通过和光气(或光气等价物如三光气)或氯甲酸烷基酯如氯甲酸甲酯在合适的溶剂如甲苯或四氢呋喃中反应来制备。
路线12
式5的吡啶基吡唑羧酸可通过路线13中描述的方法制备。吡唑12和式13的2-卤代吡啶在合适的碱如碳酸钾的存在下,在溶剂如N,N-二甲基甲酰胺或乙腈中反应,获得1-吡啶基吡唑14的良好收率,其具有对于理想的区域化学的专一性。用二异丙基酰胺锂(LDA)进行14的金属化,接着用二氧化碳使锂盐骤冷,获得式5的吡唑羧酸。
路线13
其中R2为CF3、Cl或Br的起始吡唑12为已知化合物。其中R2为CF3的吡唑12可通过文献方法(J.Fluorine Chem.1991,53(1),61-70)制备。其中R2为Cl或Br的吡唑12也可通过文献方法(H Reimlinger和A.Van Overstraeten,Chem Ber.1996,99(10),3350-7)制备。路线14描述了制备其中R2为Cl或Br的12的有用的另一方法。氨磺酰吡唑15与正丁基锂进行金属化,接着用六氯乙烷(R2为Cl)或1,2-二溴-四氯乙烷(R2为Br)进行阴离子的直接卤化,获得卤化的衍生物16(其中R2为Cl或Br)。在室温下用三氟乙酸(TFA)除去氨磺酰基可以进行得很彻底,并且以良好收率获得吡唑12,其中R2分别为Cl或Br。
路线14
作为路线13描述的方法的替代方法,其中R2为CF3的式5的吡唑羧酸也可通过路线15描述的方法制备。式17的化合物(其中R8为C1-C4烷基)在用酸如乙酸中和后,与合适的碱在合适的有机溶剂中反应,获得式18的环化产物。
路线15
合适的碱可以为,例如但不限于,氢化钠、叔丁醇钾、dimsyl钠(CH3S(O)CH2-Na+)、碱金属(如锂、钠或钾)碳酸盐或氢氧化物、四烷基(如甲基、乙基或丁基)铵氟化物或氢氧化物或2-叔丁基亚氨基-2-二乙基氨基-1,3-二甲基-全氢-1,3,2-diazaphosphonine。合适的有机溶剂可以是,例如但不限于,丙酮、乙腈、四氢呋喃、二氯甲烷、二甲亚砜或N,N-二甲基甲酰胺。环化反应通常在约0至约120℃的温度范围内进行。溶剂、碱、温度和加入时间的影响都是相互依赖的,反应条件的选择对减少副产物形成是重要的。优选的碱为叔丁基氟化铵。
式18的化合物脱水获得式19的化合物,接着羧酸酯官能团水解成羧酸,获得式5的化合物。通过用催化量的合适的酸处理来实现脱水。这一催化酸可以是,例如但不限于,硫酸。一般用有机溶剂进行反应。本领域技术人员会认识到,脱水反应可在多种溶剂,例如乙酸中,在约0至200℃的温度范围内,优选在约0至100℃的温度范围内进行。式19的羧酸酯可通过多种方法转化成式5的羧酸,所述方法包括在无水条件下的亲核裂解或包括使用酸或碱的水解方法(参见T.W.Green和P.G.M.Wuts,Protective Groups in Organic Synthesis,2nd ed.,John Wiley & Sons,Inc.,New York,1991,pp.224-269,方法综述)。对于路线15的方法,优选碱催化的水解方法。合适的碱包括碱金属(如锂、钠或钾)氢氧化物。例如,可将酯溶解在水和醇如乙醇的混合物中。当用氢氧化钠或氢氧化钾处理时,酯被皂化,获得羧酸的钠盐或钾盐。用强酸,如盐酸或硫酸酸化,获得式5的羧酸。
其中R2为CF3的式17的化合物可通过路线16描述的方法制备。用式CH3COR2的酮在溶剂如水、甲醇或乙酸中处理式20的肼化合物,获得式21的腙。
路线16
其中R2为CF3,而R8为C1-C4烷基
本领域技术人员会认识到,这一反应可能需要通过任选的酸进行催化,并且取决于式21的腙的分子取代模式,还可能需要升温。式21的腙和氯草酸烷基酯在合适的有机溶剂例如但不限于二氯甲烷或四氢呋喃中在除酸剂如三乙胺存在下反应,获得式17的化合物。反应通常在约0至100℃的温度下进行。式20的肼化合物可通过标准方法,如通过式13的相应的卤代吡啶和肼反应来制备。
作为路线13所述的方法的替代方法,其中R2为Cl或Br的式5的吡唑羧酸也可通过路线17描述的方法制备。式22的化合物任选地在酸存在下氧化,获得R2为Cl或Br的式19的化合物。羧酸酯官能团水解成羧酸,获得式5的化合物。
路线17
其中R8为C1-C4烷基
用于将式22的化合物转化成式19的化合物的氧化剂可以是过氧化氢、有机过氧化物、过硫酸钾、过硫酸钠、过硫酸铵、一过硫酸钾(例如Oxone)或高锰酸钾。为了获得彻底转化,应该使用相对于式22的化合物的至少一当量氧化剂,优选使用约1当量至约2当量。这一氧化一般在溶剂存在下进行。溶剂可以是醚,如四氢呋喃、p-二噁烷等,有机酯,如乙酸乙酯、碳酸二甲酯等,或极性非质子有机溶剂如N,N-二甲基甲酰胺、乙腈等。适用于氧化步骤的酸包括无机酸,如硫酸、磷酸等,有机酸,如乙酸、苯甲酸等。可使用1-5当量酸。优选的氧化剂为过硫酸钾,并且氧化优选在硫酸存在下进行。可通过将式22的化合物在期望的溶剂,以及酸(如果使用的话)中混合进行反应。接着以方便的速率加入氧化剂。为了获得合理的反应时间来完成反应,反应温度通常在约0℃的低温至溶剂沸点之间变化。适于将式19的酯转化成式5的羧酸的方法已在路线15中得到了描述。
其中R2为卤素而R8为C1-C4烷基的式22的化合物可如路线18中所示由式23的相应的化合物制备。
路线18
其中R8为C1-C4烷基
通常在溶剂存在下,用卤化试剂处理式23的化合物,获得式22的相应的卤代化合物。可使用的卤化试剂包括磷卤氧化物、磷三卤化物、磷五卤化物、亚硫酰二氯、二卤代三烷基正膦、二卤代二苯基正膦、草酰氯和光气。优选磷卤氧化物和磷五卤化物。为了获得彻底转化,应该使用相对于式23的化合物的至少0.33当量磷卤氧化物,优选使用约0.33至1.2当量。为了获得彻底转化,应该使用相对于式23的化合物的至少0.20当量磷五卤化物,优选使用约0.20至1.0当量。用于这一卤化的典型溶剂包括卤代烷,如二氯甲烷、氯仿、氯丁烷等,芳族溶剂,如苯、二甲苯、氯苯等,醚,如四氢呋喃、p-二噁烷、乙醚等,以及极性非质子溶剂,如乙腈、N,N-二甲基甲酰胺等。任选地可加入有机碱,如三乙胺、吡啶、N,N-二甲基苯胺等。催化剂如N,N-二甲基甲酰胺的加入也是任选的。优选的方法中溶剂为已腈,且不存在碱。一般当使用乙腈溶剂时,既不需要碱也不需要催化剂。优选的方法通过将式23的化合物在乙腈中混合来进行。接着在方便的时间内加入卤化试剂,接着将混合物保持在期望的温度下直至反应结束。反应温度一般在20℃至乙腈的沸点温度之间,而反应时间一般少于2小时。接着用无机碱如碳酸氢钠、氢氧化钠等或有机碱如乙酸钠中和反应物。可通过本领域技术人员已知的方法,包括结晶、萃取和蒸馏来分离式22的期望的产物。
或者,其中R2为Br或Cl的式22的化合物可通过分别用溴化氢或氯化氢处理其中R2为不同的卤素(例如对于制备其中R2为Br的式22而言为Cl)或磺酸酯基如对甲苯磺酸酯、苯磺酸酯和甲磺酸酯的式22的相应的化合物来制备。通过这一方法,式22的化合物上R2卤素或磺酸酯取代基分别被来自溴化氢或氯化氢的Br或Cl取代。反应在合适的溶剂如二溴甲烷、二氯甲烷、乙酸、乙酸乙酯或乙腈中进行。反应可以在大气压下或接近大气压或超过大气压的加压容器中进行。卤化试剂可以气体的形式加入含有式23的化合物和溶剂的反应混合物中。当式22的起始化合物中的R2为卤素如Cl时,反应优选以喷射或其它合适的手段除去反应产生的卤化氢的方式进行。或者,可以首先将卤化试剂溶解在其高度可溶的惰性溶剂(如乙酸)中,然后与纯的或在溶液中的式23的化合物接触。反应可在约0-100℃之间进行,最方便地在接近室温(例如约10-40℃),更优选在约20-30℃之间。路易斯酸催化剂(如用于制备其中R2为Br的式22的三溴化铝)的加入可促进反应。式22的产物通过本领域技术人员已知的常规方法,包括萃取、蒸馏和结晶进行分离。
其中R2为磺酸酯基的式22的起始化合物可由式23的相应化合物通过标准方法,如用磺酰氯(例如对甲苯磺酰氯)和碱如叔胺(例如三乙胺)在合适的溶剂如二氯甲烷中处理来制备。
作为路线13所述的方法的替代方法,其中R2为卤烷氧基的式5的吡唑羧酸也可通过路线19描述的方法制备。将式23的化合物氧化成式24的化合物。用于这一氧化的反应条件如路线17中将式22的化合物转化成式19的化合物所用的条件。
路线19
其中R2为卤烷氧基,而R8为C1-C4烷基
式24的中间体接着通过与合适的卤烷化剂如卤烷基卤或卤烷基磺酸酯反应而烷基化形成式19的化合物(其中R2为卤烷氧基)。反应在至少一当量碱的存在下进行。合适的碱包括无机碱,如碱金属(如锂、钠或钾)碳酸盐、氢氧化物和氢化物,或有机碱,如三乙胺、二异丙基乙胺和1,8-二氮杂二环[5.4.0]十一-7-烯。反应一般在溶剂中进行,溶剂可包括醇,如甲醇和乙醇,卤代烷,如二氯甲烷,芳族溶剂,如苯、甲苯和氯苯,醚,如四氢呋喃,极性非质子溶剂,如乙腈、N,N-二甲基甲酰胺等。醇和极性非质子溶剂优选与无机碱一起使用。碳酸钾作为碱及N,N-二甲基甲酰胺或乙腈作为溶剂是优选的。反应一般在0-150℃之间进行,最通常在室温至100℃之间进行。接着可通过如路线15中描述将式19的化合物转化成式5的化合物的方法将式24的酯转化成式5的羧酸。
式23的化合物可从式20的化合物如路线20描述来制备。在该方法中,使式20的肼化合物与式25的化合物(可使用其富马酸酯或马来酸酯或它们的混合物)在碱和溶剂存在下反应。
路线20
其中R8为C1-C4烷基
路线20中所用的碱通常为金属醇盐,如甲醇钠、甲醇钾、乙醇钠、乙醇钾、叔丁醇钾、叔丁醇锂等。可使用极性质子和极性非质子有机溶剂,如醇、乙腈、四氢呋喃、N,N-二甲基甲酰胺、二甲亚砜等。优选的溶剂为醇,如甲醇和乙醇。特别优选醇与构成富马酸酯或马来酸酯和醇盐碱的醇相同。反应通常通过在溶剂中混合式20的化合物和碱来进行。可将混合物加热或冷却至期望的温度,并在一段时间内加入式25的化合物。通常反应温度在0℃至所用溶剂的沸点之间。为了提高溶剂的沸点,可以在大于大气压的压力下进行反应。温度在约30-90℃之间通常是优选的。接着可通过加入有机酸如乙酸等,或无机酸如盐酸、硫酸等来酸化反应物。可以通过本领域技术人员已知的方法如结晶、萃取或蒸馏分离式23的期望的产物。
应认识到,以上所述用于制备式1的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。在这些情况下,将保护/脱保护步骤或官能团互相转换引入合成中将有助于获得期望的产物。保护基的使用和选择对于化学合成领域的技术人员而言将是清楚的(例如参阅T.W.,Greene和P.G.M.Wuts,Protective Groups inOrganic Synthesis,2nd ed.;Wiley:New York,1991)。本领域技术人员会认识到,在某些情况中,如任何单个机理中描述引入给定试剂后,可能需要实施没有详细描述的附加路线合成步骤来完成式I的化合物的合成。本领域技术人员还会认识到,可能需要以不同于所示的特定顺序的顺序实施在上述路线中所述的步骤的组合来制备式I的化合物。
不用进一步详细描述,相信本领域技术人员使用前面的说明可以最大程度地使用本发明。因此,以下实施例只是说明性的,而不以任何方式限制本发明的内容。以下实施例中的步骤阐明整个合成转化中每一步骤的过程,并且每一步骤的原料不一定通过在其它实施例或步骤中描述的特定制备过程制备。除了对于色谱溶剂混合物而言或者另作说明以外,百分比均为重量百分比。除非另有说明,色谱溶剂混合物的份数和百分比指体积份和体积百分比。1H NMR谱是从四甲基硅烷向低场以ppm为单位报道的;“s”是单峰,“d”是双峰,“t”是三重峰,“q”是四重峰,“m”是多重峰,“dd”是两个双峰,“dt”是两个三重峰,“brs”是宽的单峰。
实施例1
1-(3-氯-2-吡啶基)-N-[4-氰基-2-甲基-6-(氨基羰基)苯基]-3-(三氟甲基)-1H-吡唑-5-甲酰胺的制备
步骤A:2-氨基-3-甲基-5-碘苯甲酸的制备
向2-氨基-3-甲基苯甲酸(Aldrich,5g,33mmol)在N,N-二甲基甲酰胺(30mL)中的溶液中加入N-碘琥珀酰亚胺(7.8g,34.7mmol),并将反应混合物悬浮在75℃油浴中过夜。移开加热器,然后将反应混合物缓慢倾入冰水(100mL)中,以沉淀浅灰色固体。过滤固体并用水洗涤四次,然后放置在70℃的真空炉中干燥过夜。分离期望的浅灰色固体中间体(8.8g)。
1H NMR(DMSO-d6):δ7.86(d,1H),7.44(d,1H),2.08(s,3H)。
步骤B:3-氯-2-[3-(三氟甲基)-1H-吡唑-1-基]吡啶的制备
向2,3-二氯吡啶(99.0g,0.67mol)和3-(三氟甲基)-吡唑(83g,0.61mol)在N,N-二甲基甲酰胺(300mL)中的混合物中加入碳酸钾(166.0g,1.2mol),接着将反应物在48小时内加热到110-125℃。将反应物冷却至100℃,并通过Celite硅藻土助滤剂过滤以除去固体。通过在常压下蒸馏除去N,N-二甲基甲酰胺和过量的二氯吡啶。在减压(沸点139-141℃,7mm)下蒸馏,获得113.4g期望的亮黄色油状物中间体。
1H NMR(CDCl3):δ8.45(d,1H),8.15(s,1H),7.93(d,1H),7.36(t,1H),6.78(s,1H)。
步骤C:1-(3-氯-2-吡啶基)-3-(三氟甲基)-1H-吡唑-5-羧酸的制备
在-75℃下,向3-氯-2-[3-(三氟甲基)-1H-吡唑-1-基]吡啶(即步骤B的吡唑产物)(105.0g,425mmol)在无水四氢呋喃(700mL)中的溶液中经套管加入-30℃的二异丙基酰胺锂(425mmol)在无水四氢呋喃(300mL)中的溶液。将深红色溶液搅拌15分钟,此后于-63℃下鼓入二氧化碳,直到溶液变成淡黄色并且放热停止。将反应物再搅拌20分钟,接着用水(20mL)终止反应。在减压下除去溶剂,并使反应混合物在乙醚和0.5N氢氧化钠水溶液之间分配。用乙醚洗涤水萃取液(3x),过滤通过Celite硅藻土助滤剂以除去残余固体,接着酸化至pH约为4,此时形成橙色油状物。剧烈搅拌水混合物并再加入酸使pH降低到2.5-3。橙色油状物凝结成粒状固体,过滤之,接连用水和1N盐酸洗涤,于50℃下真空干燥,获得130g标题化合物白色固体。来自另一相似过程的操作的产物在175-176℃下熔化。
1H NMR(DMSO-d6):δ7.61(s,1H),7.76(dd,1H),8.31(d,1H),8.60(d,1H)。
步骤D:2-[1-(3-氯-2-吡啶基)-3-(三氟甲基)-1H-吡唑-5-基]-6-碘-8-甲基-4H-3,1-苯并噁嗪-4-酮的制备
在-5℃下,向甲磺酰氯(2.91mL,37.74mmol)在乙腈(50mL)中的溶液中逐滴加入1-(3-氯-2-吡啶基)-3-(三氟甲基)-1H-吡唑-5-羧酸(即步骤C的羧酸产物)(10.0g,34.31mmol)和三乙胺(4.78mL,34.31mmol)在乙腈(50mL)中的混合物。然后在整个连续试剂加入期间将反应温度维持在0℃。在搅拌20分钟后,加入2-氨基-3-甲基-5-碘苯甲酸(即步骤A的产物)(9.51g,34.31mmol),并且继续再搅拌10分钟。然后逐滴加入三乙胺(9.56mL,68.62mmol)在乙腈(15mL)中的溶液,并将反应混合物搅拌30分钟,接着加入甲磺酰氯(2.91mL,37.74mmol)。然后使反应混合物暖至室温,并搅拌2小时。在减压下蒸发溶剂,通过硅胶色谱纯化残余物,获得8.53g标题化合物黄色固体。
1H NMR(CDCl3):δ8.59(dd,1H),8.35(d,1H),7.97(dd,1H),7.86(d,1H),7.49(m,2H),1.79(s,3H)。
步骤E:2-[1-(3-氯-2-吡啶基)-3-(三氟甲基)-1H-吡唑-5-基]-6-氰基-8-甲基-4H-3,1-苯并噁嗪-4-酮的制备
在室温下,向2-[1-(3-氯-2-吡啶基)-3-(三氟甲基)-1H-吡唑-5-基]-6-碘-8-甲基-4H-3,1-苯并噁嗪-4-酮(即步骤D的苯并噁嗪酮产物)(500mg,0.94mmol)在四氢呋喃(10mL)中的溶液中依次加入碘化铜(I)(180mg,0.094mmol)、四(三苯基膦)钯(O)(5.4mg,0.047mmol)和氰化铜(I)(420mg,4.7mmol)。将反应混合物加热回流过夜后,再加入氰化铜(I)(420mg,4.7mmol)、碘化铜(I)(107mg,0.56mmol)和四(三苯基膦)钯(O)(325mg,0.28mmol),并继续回流1小时。反应混合物颜色变黑,此时硅胶薄层色谱证实反应结束。接着用乙酸乙酯(20mL)稀释反应混合物,并过滤通过Celite,接着用10%碳酸氢钠水溶液洗涤三次,并用盐水洗涤一次。干燥有机萃取液(MgSO4),并且在减压下浓缩,获得410mg标题化合物黄色固体粗产物。
1H NMR(CDCl3):δ8.59(dd,1H),8.33(d,1H),8.03(dd,1H),7.95(d,1H),7.56(m,2H),1.88(s,3H)。
步骤F:1-(3-氯-2-吡啶基)-N-[4-氰基-2-甲基-6-(氨基羰基)苯基]-3-(三氟甲基)-1H-吡唑-5-甲酰胺的制备
在室温下,向2-[1-(3-氯-2-吡啶基)-3-(三氟甲基)-1H-吡唑-5-基]-6-氰基-8-甲基-4H-3,1-苯并噁嗪-4-酮(即步骤E的氰基苯并噁嗪酮产物)(200mg,0.46mmol)在四氢呋喃(5mL)中的溶液中逐滴加入氢氧化铵(0.5mL,12.8mmol)。接着将反应混合物搅拌5分钟,此时硅胶薄层色谱证实反应结束。在减压下蒸发四氢呋喃溶剂,通过硅胶色谱纯化残余固体,获得620mg标题化合物,即本发明的化合物固体,熔点为200-202℃。
1H NMR(CDCl3):δ10.65(s,1H),8.43(dd,1H),7.9(dd,1H),7.67(s,1H),7.63(s,1H),7.45(m,1H),7.25(s,1H),6.21(bs,1H),5.75(bs,1H),2.26(s,3H)。
实施例2
1-(3-氯-2-吡啶基)-N-[4-氰基-2-甲基-6-[(甲氨基)羰基]苯基]-3-(三氟甲基)-1H-吡唑-5-甲酰胺的制备
步骤A:1-(3-氯-2-吡啶基)-N-[4-碘-2-甲基-6-[(甲氨基)羰基]苯基]-3-(三氟甲基)-1H-吡唑-5-甲酰胺的制备
向2-[1-(3-氯-2-吡啶基)-3-(三氟甲基)-1H-吡唑-5-基]-6-碘-8-甲基-4H-3,1-苯并噁嗪-4-酮(即实施例1,步骤D的苯并噁嗪酮产物)(500mg,0.94mmol)在四氢呋喃(15mL)中的溶液中逐滴加入甲胺(在THF中的0.2M溶液,1.4mL,2.8mmol),并将反应混合物搅拌3小时,此时硅胶薄层色谱证实反应结束。在减压下蒸发四氢呋喃溶剂,通过硅胶色谱纯化残余固体,获得400mg标题化合物黄色固体。
1H NMR(CDCl3):δ10.25(s,1H),8.45(dd,1H),7.85(dd,1H),7.55(s,1H),7.50(s,1H),7.46(s,1H),7.40(m,1H),6.15(d,1H),2.93(d,3H),2.12(s,3H)。
步骤B:1-(3-氯-2-吡啶基)-N-[4-氰基-2-甲基-6-[(甲氨基)羰基]苯基]-3-(三氟甲基)-1H-吡唑-5-甲酰胺的制备
在室温下,向1-(3-氯-2-吡啶基)-N-[4-碘-2-甲基-6-[(甲氨基)羰基]苯基]-3-(三氟甲基)-1H-吡唑-5-甲酰胺(即步骤A的diamide产物)(410mg,0.72mmol)在四氢呋喃(8mL)中的溶液中依次加入碘化铜(I)(24mg,0.126mmol)、四(三苯基膦)钯(O)(70mg,0.060mmol)和氰化铜(I)(640mg,7.2mmol)。将反应混合物加热回流4.5小时。硅胶薄层色谱证实反应结束。接着用乙酸乙酯(20mL)稀释反应混合物,并过滤通过Celite,接着用10%碳酸氢钠水溶液洗涤三次,并用盐水洗涤一次。干燥有机萃取液(MgSO4),并且在减压下浓缩,通过硅胶色谱纯化残余物,获得114mg标题化合物,本发明的化合物白色固体,熔点为214-216℃。
1H NMR(CDCl3):δ10.70(s,1H),8.46(dd,1H),7.87(dd,1H),7.57(s,2H),7.45(m,1H),7.31(s,1H),6.35(d,1H),2.98(d,3H),2.24(s,3H)。
实施例3
3-氯-1-(3-氯-2-吡啶基)-N-[4-氰基-2-甲基-6-[(甲基氨基)羰基]苯基]-1H-吡唑-5-甲酰胺的制备
步骤A:3-氯-N,N-二甲基-1H-吡唑-1-磺酰胺的制备
在-78℃下,向N,N-二甲基氨磺酰吡唑(188.0g,1.07mol)在无水四氢呋喃(1500mL)中的溶液中逐滴加入正丁基锂(472mL,1.18mol)在己烷中的2.5M溶液,同时维持温度低于-65℃。加完后,将反应混合物在-78℃下再维持45分钟,此后逐滴加入六氯乙烷(279g,1.18mol)在四氢呋喃(120mL)中的溶液。将反应混合物在-78℃下维持1小时,暖至-20℃,接着用水(1L)终止反应。用二氯甲烷萃取反应混合物(4×500mL);干燥有机萃取液(MgSO4)并浓缩。通过硅胶色谱用二氯甲烷作为洗脱剂进一步纯化粗产物,获得160g标题化合物黄色油状物。
1H NMR(CDCl3):δ7.61(s,1H),6.33(s,1H),3.07(d,6H)。
步骤B:3-氯吡唑的制备
向三氟乙酸(290mL)中逐滴加入3-氯-N,N-二甲基-1H-吡唑-1-磺酰胺(即步骤A的氯吡唑产物)(160g),将反应混合物在室温下搅拌1.5小时,接着在减压下浓缩。将残余物收集(take up)在己烷中,滤除不溶的固体,并浓缩己烷,获得粗产物油状物。通过硅胶色谱用乙醚/己烷(40∶60)作为洗脱剂进一步纯化粗产物,获得64.44g标题化合物黄色油状物。
1H NMR(CDCl3):δ6.39(s,1H),7.66(s,1H),9.6(br s,1H)。
步骤C:3-氯-2-(3-氯-1H-吡唑基-1-基)吡啶的制备
向2,3-二氯吡啶(92.60g,0.629mol)和3-氯吡唑(即步骤B的产物)(64.44g,0.629mol)在N,N-二甲基甲酰胺(400mL)中的混合物中加入碳酸钾(147.78g,1.06mol),接着将反应混合物加热至100℃,持续36小时。将反应混合物冷却至室温,并缓慢倾入冰水中。过滤沉淀的固体并用水洗涤。将固体滤饼收集在乙酸乙酯中,用硫酸镁干燥,并浓缩。用20%乙酸乙酯/己烷作为洗脱剂对粗产物固体进行硅胶色谱分离,获得39.75g标题化合物白色固体。
1H NMR(CDCl3):δ6.43(s,1H),7.26(m,1H),7.90(d,1H),8.09(s,1H),8.41(d,1H)。
步骤D:3-氯-1-(3-氯-2-吡啶基)-1H-吡唑-5-羧酸的制备
在-78℃下,向3-氯-2-(3-氯-1H-吡唑基-1-基)吡啶(即步骤C的吡唑产物)(39.75g,186mmol)在无水四氢呋喃(400mL)中的溶液中逐滴加入二异丙基酰胺锂(93mL,186mmol)在四氢呋喃中的2.0M溶液。将二氧化碳鼓入琥珀色溶液中,持续14分钟,此后溶液变成浅棕黄色。用1N氢氧化钠水溶液调节反应物为碱性,并用乙醚萃取(2×500mL)。用6N盐酸酸化水萃取液,接着用乙酸乙酯萃取(3×500mL)。用硫酸镁干燥乙酸乙酯萃取液,并浓缩,获得42.96g标题产物乳白色固体。来自相同过程的另一操作的产物在198-199℃下熔解。
1H NMR(DMSO-d6):δ6.99(s,1H),7.45(m,1H),7.93(d,1H),8.51(d,1H)。
步骤E:2-[3-氯-1-(3-氯-2-吡啶基)-1H-吡唑-5-基]-6-碘-8-甲基-4H-3,1-苯并噁嗪-4-酮的制备
在0℃下,向甲磺酰氯(0.63mL,8.13mmol)在乙腈(10mL)中的溶液中逐滴加入3-氯-1-(3-氯-2-吡啶基)-1H-吡唑-5-羧酸(即步骤D的羧酸产物)(2.0g,7.75mmol)和三乙胺(1.08mL,7.75mmol)在乙腈(5mL)中的混合物。将反应混合物在0℃下搅拌15分钟。接着加入2-氨基-3-甲基-5-碘苯甲酸(即实施例1,步骤A的产物)(2.14g,7.75mmol),并继续再搅拌5分钟。接着逐滴加入三乙胺(2.17mL,15.15mmol)在乙腈(5mL)中的溶液,同时保持温度低于5℃。将反应混合物在0℃下搅拌40分钟,接着加入甲磺酰氯(0.63mL,8.13mmol)。接着将反应混合物暖至室温并搅拌过夜。接着用水(50mL)稀释反应混合物,并用乙酸乙酯萃取(3×50mL)。依次用10%碳酸氢钠水溶液(1×20mL)和盐水(1×20mL)洗涤合并的乙酸乙酯萃取液,干燥(MgSO4)并浓缩,获得3.18g标题化合物黄色固体粗产物。
1H NMR(CDCl3):δ8.55(dd,1H),8.33(s,1H),7.95(dd,1H),7.82(d,1H),7.45(m,1H),7.16(s,1H),1.77(s,3H)。
步骤F:2-[3-氯-1-(3-氯-2-吡啶基)-1H-吡唑-5-基]-6-氰基-8-甲基-4H-3,1-苯并噁嗪-4-酮的制备
在室温下,向2-[3-氯-1-(3-氯-2-吡啶基)-1H-吡唑-5-基]-6-碘-8-甲基-4H-3,1-苯并噁嗪-4-酮(即步骤E的苯并噁嗪酮产物)(600mg,1.2mmol)在四氢呋喃(15mL)中的溶液中依次加入碘化铜(I)(137mg,0.72mmol)、四(三苯基膦)钯(O)(416mg,0.36mmol)和氰化铜(I)(860mg,9.6mmol)。接着将反应混合物加热回流过夜。反应物颜色变成黑色,此时硅胶薄层色谱证实反应结束。用乙酸乙酯(20mL)稀释反应物,并过滤通过Celite,接着用10%碳酸氢钠水溶液洗涤三次,并用盐水洗涤一次。干燥有机萃取液(MgSO4),并在减压下浓缩,获得397mg标题化合物黄色固体粗产物。
1H NMR(CDCl3):δ8.50(q,1H),8.22(d,1H),7.90(dd,1H),7.67(d,1H),7.45(m,1H),7.15(s,1H),1.79(s,3H)。
步骤G:3-氯-1-(3-氯-2-吡啶基)-N-[4-氰基-2-甲基-6-(甲氨基)羰基]苯基]-1H-吡唑-5-甲酰胺的制备
向2-[3-氯-1-(3-氯-2-吡啶基)-1H-吡唑-5-基]-6-氰基-8-甲基-4H-3,1-苯并噁嗪-4-酮(即步骤F的氰基苯并噁嗪酮产物)(100mg,0.25mmol)在四氢呋喃(15mL)中的溶液中逐滴加入甲胺(在四氢呋喃中的2.0M溶液,0.5mL,1.0mmol),并将反应混合物搅拌5分钟,此时硅胶薄层色谱证实反应结束。在减压下蒸发四氢呋喃溶剂,通过硅胶色谱纯化残余固体,获得标题化合物,本发明的化合物白色固体(52mg),它在高于140℃的熔点测定器中分解。
1H NMR(CDCl3):δ10.55(s,1H),8.45(dd,1H),7.85(dd,1H),7.55(d,2H),7.40(m,1H),6.97(d,1H),6.30(d,1H),2.98(d,3H),2.24(d,3H)。
实施例4
3-氯-1-(3-氯-2-吡啶基)-N-[4-氰基-2-甲基-6-(氨基羰基)苯基]-1H-吡唑-5-甲酰胺的制备
在室温下,向2-[3-氯-1-(3-氯-2-吡啶基)-1H-吡唑-5-基]-6-氰基-8-甲基-4H-3,1-苯并噁嗪-4-酮(即实施例3,步骤F的氰基苯并噁嗪酮产物)(100mg,0.25mmol)在四氢呋喃(5mL)中的溶液中逐滴加入氢氧化铵(0.5mL,12.8mmol)。接着将反应混合物搅拌5分钟,此时硅胶薄层色谱证实反应结束。在减压下蒸发四氢呋喃溶剂,通过硅胶色谱纯化残余固体,获得55mg标题化合物,本发明的化合物白色固体(52mg),它在高于255°℃的熔点测定器中分解。
1H NMR(CDCl3):δ10.50(s,1H),8.45(dd,1H),7.85(dd,1H),7.66(d,1H),7.61(s,1H),7.41(m,1H),6.95(s,1H),6.25(bs,1H),5.75(bs,1H),2.52(s,3H)。
实施例5
3-溴-1-(3-氯-2-吡啶基)-N-[4-氰基-2-甲基-6-[(甲氨基)羰基]苯基)-1H-吡唑-5-甲酰胺的制备
步骤A:3-溴-N,N-二甲基-1H-吡唑-1-磺酰胺的制备
在-78℃下,向N,N-二甲基氨磺酰吡唑(44.0g,0.251mol)在无水四氢呋喃(500mL)中的溶液中逐滴加入正丁基锂溶液(2.5M,在己烷中,105.5mL,0.264mol),同时维持温度低于-60℃。加入过程中形成粘稠固体。加完后,将反应混合物再放置15分钟,此后逐滴加入1,2-二溴-四氯乙烷(90g,0.276mol)在四氢呋喃(150mL)中的溶液,同时维持温度低于-70℃。反应混合物变成澄清的橙色;再继续搅拌15分钟。移去-78℃浴,用水(600mL)终止反应。用二氯甲烷萃取反应混合物(4x),用硫酸镁干燥有机萃取液,并浓缩。通过硅胶色谱用二氯甲烷-己烷(50∶50)作为洗脱剂进一步纯化粗产物,获得57.04g标题产物澄清无色油状物。
1H NMR(CDCl3):δ3.07(d,6H),6.44(m,1H),7.62(m,1H)。
步骤B:3-溴吡唑的制备
向三氟乙酸(70mL)中缓慢加入3-溴-N,N-二甲基-1H-吡唑-1-磺酰胺(即步骤A的溴吡唑产物)(57.04g)。将反应混合物在室温下搅拌30分钟,接着在减压下浓缩。将残余物收集在己烷中,滤除不溶的固体,蒸发己烷,获得粗产物油状物。通过硅胶色谱用乙酸乙酯/二氯甲烷(10∶90)作为洗脱剂进一步纯化粗产物,获得油状物。将该油状物收集在二氯甲烷中,用碳酸氢钠水溶液中和,用二氯甲烷萃取(3x),用硫酸镁干燥,并浓缩,获得25.9g标题产物白色固体,m.p.61-64℃。
1H NMR(CDCl3):δ6.37(d,1H),7.59(d,1H),12.4(br s,1H)。
步骤C:2-(3-溴-1H-吡唑-1-基)-3-氯吡啶的制备
向2,3-二氯吡啶(27.4g,185mmol)和3-溴吡唑(即步骤B的产物)(25.4g,176mmol)在无水N,N-二甲基甲酰胺(88mL)中的混合物中加入碳酸钾(48.6g,352mmol),并将反应混合物加热到125℃,持续18小时。将反应混合物冷却至室温,并缓慢倾入冰水(800mL)中。形成沉淀。将沉淀的固体搅拌1.5小时,过滤并用水洗涤(2×100mL)。将固体滤饼收集在二氯甲烷中,并依次用水、1N盐酸、饱和碳酸氢钠溶液和盐水洗涤。接着用硫酸镁干燥有机萃取液,并浓缩,获得39.9g粉色固体。将粗产物悬浮在己烷中,并剧烈搅拌1小时。过滤固体,用己烷洗涤,并干燥,获得标题产物乳白色粉末(30.4g),NMR测定的纯度>94%。该物质可不进一步纯化而用于步骤D中。
1H NMR(CDCl3):δ6.52(s,1H),7.30(dd,1H),7.92(d,1H),8.05(s,1H),8.43(d,1H)。
步骤D:3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-羧酸的制备
在-76℃下,向2-(3-溴-1H-吡唑-1-基)-3-氯吡啶(即步骤C的吡唑产物)(30.4g,118mmol)在无水四氢呋喃(250mL)中的溶液中逐滴加入二异丙基酰胺锂(118mmol)在四氢呋喃中的溶液,加入速率使反应温度维持低于-71℃。将反应混合物在-76℃下搅拌15分钟,接着鼓入二氧化碳,持续10分钟,使温度暖至-57℃。使反应混合物暖至-20℃,并用水终止反应。浓缩反应混合物,并接着收集在水(1L)和乙醚(500mL)中,接着加入氢氧化钠水溶液(1N,20mL)。用乙醚洗涤水萃取液,并用盐酸酸化。过滤沉淀的固体,用水洗涤,并干燥,获得27.7g标题产物褐色固体。来自相同过程的另一操作的产物在200-201℃下熔解。
1H NMR(DMSO-d6):δ7.25(s,1H),7.68(dd,1H),8.24(d,1H),8.56(d,1H)。
步骤E:2-[3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-基]-6-碘-8-甲基-4H-3,1-苯并噁嗪-4-酮的制备
在0℃下,向甲磺酰氯(0.54mL,6.94mmol)在乙腈(15mL)中的溶液中逐滴加入3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-羧酸(即步骤D的羧酸产物)(2.0g,6.6mmol)和三乙胺(0.92mL,6.6mmol)在乙腈(5mL)中的混合物。然后将反应混合物在0℃下搅拌15分钟。接着加入2-氨基-3-甲基-5-碘苯甲酸(即实施例1,步骤A的产物)(1.8g,6.6mmol),继续再搅拌5分钟。然后逐滴加入三乙胺(1.85mL,13.2mmol)在乙腈(5mL)中的溶液,同时保持温度低于5℃。将反应混合物在0℃下搅拌40分钟,然后加入甲磺酰氯(0.54mL,6.94mmol)。然后使反应混合物暖至室温并搅拌过夜。然后用水(50mL)稀释反应混合物,并用乙酸乙酯萃取(3×50mL)。依次用10%碳酸氢钠水溶液(1×20mL)和盐水(1×20mL)洗涤合并的乙酸乙酯萃取液,干燥(MgSO4)并浓缩,获得2.24g标题产物黄色固体粗产物。
1H NMR(CDCl3):δ8.55(dd,1H),8.33(d,1H),7.95(dd,1H),7.85(s,1H),7.45(m,1H),7.25(s,1H),1.77(s,3H)。
步骤F:2-[3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-基]-6-氰基-8-甲基-4H-3,1-苯并噁嗪-4-酮的制备
在室温下,向2-[3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-基]-6-碘-8-甲基-4H-3,1-苯并噁嗪-4-酮(即步骤E的苯并噁嗪酮产物)(600mg,1.1mmol)在四氢呋喃(15mL)中的溶液中依次加入碘化铜(I)(126mg,0.66mmol)、四(三苯基膦)钯(O)(382mg,0.33mmol)和氰化铜(I)(800mg,8.8mmol)。然后将反应混合物加热回流过夜。反应物颜色变成黑色,此时硅胶薄层色谱证实反应结束。用乙酸乙酯(20mL)稀释反应混合物,并过滤通过Celite,接着用10%碳酸氢钠溶液洗涤三次,并用盐水洗涤一次。干燥有机萃取液(MgSO4),并在减压下浓缩,获得440mg标题化合物黄色固体粗产物。
1H NMR(CDCl3):δ8.55(m,1H),8.31(d,1H),7.96(dd,1H),7.73(s,1H),7.51(m,1H),7.31(s,1H),1.86(s,3H)。
步骤G:3-溴-1-(3-氯-2-吡啶基)-N-[4-氰基-2-甲基-6-(甲氨基)羰基]苯基]-1H-吡唑-5-甲酰胺的制备
向2-[3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-基]-6-氰基-8-甲基-4H-3,1-苯并噁嗪-4-酮(即步骤F的氰基苯并噁嗪酮产物)(100mg,0.22mmol)在四氢呋喃(5mL)中的溶液中逐滴加入甲胺(在THF中的2.0M溶液,0.5mL,1.0mmol),并将反应混合物搅拌5分钟,此时硅胶薄层色谱证实反应结束。在减压下蒸发四氢呋喃溶剂,通过硅胶色谱纯化残余固体,获得标题化合物,本发明的化合物白色固体(41mg),它在高于180℃的熔点测定器中分解。
1H NMR(CDCl3):δ10.55(s,1H),8.45(dd,1H),7.85(dd,1H),7.57(s,2H),7.37(m,1H),7.05(s,1H),6.30(d,1H),2.98(d,3H),2.24(s,3H)。
实施例6
3-溴-1-(3-氯-2-吡啶基)-N-[4-氰基-2-甲基-6-(氨基羰基)苯基]-1H-吡唑-5-甲酰胺的制备
在室温下,向2-[3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-基]-6-氰基-8-甲基-4H-3,1-苯并噁嗪-4-酮(即实施例5,步骤F的氰基苯并噁嗪酮产物)(100mg,0.22mmol)在四氢呋喃(5mL)中的溶液中逐滴加入氢氧化铵(0.5mL,12.8mmol)。然后将反应混合物搅拌5分钟,此时硅胶薄层色谱证实反应结束。在减压下蒸发四氢呋喃溶剂,通过硅胶色谱纯化残余固体,获得标题化合物,本发明的化合物白色固体(36mg),其熔点高于255℃。
1H NMR(CDCl3):δ10.52(s,1H),8.45(dd,1H),7.85(dd,1H),7.65(s,1H),7.60(s,1H),7.40(m,1H),7.05(s,1H),6.20(bs,1H),5.75(bs,1H),2.25(s,3H)。
实施例7
3-氯-1-(3-氯-2-吡啶基)-N-[2-氯-4-氰基-6-[(甲氧基)羰基]苯基)-1H-吡唑-5-甲酰胺的制备
步骤A:2-氨基-3-氯-5-碘苯甲酸的制备
向2-氨基-3-氯苯甲酸(Aldrich,5g,29.1mmol)在N,N-二甲基甲酰胺(30mL)中的溶液中加入N-碘琥珀酰亚胺(5.8g,26mmol),并将反应混合物在60℃下加热过夜。移开加热器,然后将反应混合物缓慢倾入冰水(100mL)中以沉淀浅棕色固体。过滤固体并用水洗涤四次,然后放置在70℃的真空炉中干燥过夜。分离期望的浅棕色固体中间体(7.2g)。
1H NMR(DMSO-d6):δ7.96(d,1H),7.76(t,1H)。
步骤B:8-氯-2-[3-氯-1-(3-氯-2-吡啶基)-1H-吡唑-5-基]-6-碘-4H-3,1-苯并噁嗪-4-酮的制备
在0℃下,向甲磺酰氯(0.31mL,4.07mmol)在乙腈(10mL)中的溶液中逐滴加入3-氯-1-(3-氯-2-吡啶基)-1H-吡唑-5-羧酸(即实施例3,步骤D的羧酸产物)(1.0g,3.87mmol)和三乙胺(0.54mL,3.87mmol)在乙腈(5mL)中的混合物。然后将反应混合物在0℃下搅拌15分钟。然后加入2-氨基-3-氯-5-碘苯甲酸(即步骤A的产物)(1.15g,3.87mmol),继续再搅拌5分钟。然后逐滴加入三乙胺(1.08mL,7.74mmol)在乙腈(5mL)中的溶液,同时保持温度低于5℃。将反应混合物在0℃下搅拌40分钟,接着加入甲磺酰氯(0.31mL,4.07mmol)。然后使反应混合物暖至室温并搅拌过夜。然后用水(50mL)稀释反应混合物,并用乙酸乙酯萃取(3×50mL)。依次用10%碳酸氢钠水溶液(1×20mL)和盐水(1×20mL)洗涤合并的乙酸乙酯萃取液,干燥(MgSO4)并在减压下浓缩。通过硅胶色谱纯化残余固体,获得575mg标题化合物黄色固体粗产物。
1H NMR(CDCl3):δ8.55(q,1H),8.39(d,1H),8.04(d,1H),7.94(dd,1H),7.45(m,1H),7.19(s,1H)。
步骤C:8-氯-2-[3-氯-1-(3-氯-2-吡啶基)-1H-吡唑-5-基]-6-氰基-4H-3,1-苯并噁嗪-4-酮的制备
在室温下,向8-氯-2-[3-氯-1-(3-氯-2-吡啶基)-1H-吡唑-5-基]-6-碘-4H-3,1-苯并噁嗪-4-酮(即步骤B的苯并噁嗪酮产物)(575mg,1.1mmol)在四氢呋喃(15mL)中的溶液中依次加入碘化铜(I)(840mg,0.44mmol)、四(三苯基膦)钯(O)(255mg,0.22mmol)和氰化铜(I)(500mg,5.5mmol)。然后将反应混合物加热回流过夜。反应物颜色变成黑色,此时硅胶薄层色谱证实反应结束。用乙酸乙酯(20mL)稀释反应物,并过滤通过Celite,然后用10%碳酸氢钠水溶液洗涤三次,并用盐水洗涤一次。干燥有机萃取液(MgSO4),并在减压下浓缩,获得375mg标题化合物黄色固体粗产物。
1H NMR(CDCl3):δ8.55(q,1H),8.36(d,1H),7.95(m,2H),7.5(m,1H)。
步骤D:3-氯-1-(3-氯-2-吡啶基)-N-[2-氯-4-氰基-6-[(甲氨基)羰基]苯基]-1H-吡唑-5-甲酰胺的制备
向8-氯-2-[3-氯-1-(3-氯-2-吡啶基)-1H-吡唑-5-基]-6-氰基-4H-3,1-苯并噁嗪-4-酮(即步骤C的氰基苯并噁嗪酮产物)(187mg,0.446mmol)在四氢呋喃(5mL)中的溶液中逐滴加入甲胺(在THF中的2.0M溶液,0.5mL,1.0mmol),并将反应混合物搅拌5分钟,此时硅胶薄层色谱证实反应结束。在减压下蒸发四氢呋喃溶剂,通过硅胶色谱纯化残余固体,获得49mg标题化合物,本发明的化合物白色固体,其在197-200℃下熔解。
1H NMR(CDCl3):δ10.05(bs,1H),8.45(q,1H),7.85(dd,1H),7.70(d,1H),7.59(d,1H),7.38(m,1H),7.02(s,1H),6.35(d,1H),2.94(d,3H)。
通过本文描述的方法和本领域公知的方法,可以制备以下表1的化合物。在表中使用下列缩写:t意为叔,s意为仲,n意为正,i意为异,Me意为甲基,Et是乙基,Pr是丙基,i-Pr是异丙基,Bu是丁基,而CN是氰基。
表1
R1 | R2 | R3 | R4 | R5 | R1 | R2 | R3 | R4 | R5 |
Me | Cl | F | H | H | Cl | Cl | F | H | H |
Me | Cl | F | Me | H | Cl | Cl | F | Me | H |
Me | Cl | F | Et | H | Cl | Cl | F | Et | H |
Me | Cl | F | i-Pr | H | Cl | Cl | F | i-Pr | H |
Me | Cl | F | t-Bu | H | Cl | Cl | F | t-bu | H |
Me | Cl | F | CH2CN | H | Cl | Cl | F | CH2CN | H |
Me | Cl | F | CH(Me)CH2SMe | H | Cl | Cl | F | CH(Me)CH2SMe | H |
Me | Cl | F | C(Me)2CH2SMe | H | Cl | Cl | F | C(Me)2CH2SMe | H |
Me | Cl | F | Me | Me | Cl | Cl | F | Me | Me |
Me | Cl | Cl | H | H | Cl | Cl | Cl | H | H |
Me | Cl | Cl | Me | H | Cl | Cl | Cl | Me | H |
Me | Cl | Cl | Et | H | Cl | Cl | Cl | Et | H |
Me | Cl | Cl | i-Pr | H | Cl | Cl | Cl | i-Pr | H |
Me | Cl | Cl | t-Bu | H | Cl | Cl | Cl | t-Bu | H |
Me | Cl | Cl | CH2CN | H | Cl | Cl | Cl | CH2CN | H |
Me | Cl | Cl | CH(Me)CH2SMe | H | Cl | Cl | Cl | CH(Me)CH2SMe | H |
Me | Cl | Cl | C(Me)2CH2SMe | H | Cl | Cl | Cl | C(Me)2CH2SMe | H |
Me | Cl | Cl | Me | Me | Cl | Cl | Cl | Me | Me |
Me | Cl | Br | H | H | Cl | Cl | Br | H | H |
Me | Cl | Br | Me | H | Cl | Cl | Br | Me | H |
Me | Cl | Br | Et | H | Cl | Cl | Br | Et | H |
Me | Cl | Br | i-Pr | H | Cl | Cl | Br | i-Pr | H |
Me | Cl | Br | t-Bu | H | Cl | Cl | Br | t-Bu | H |
Me | Cl | Br | CH2CN | H | Cl | Cl | Br | CH2CN | H |
Me | Cl | Br | CH(Me)CH2SMe | H | Cl | Cl | Br | CH(Me)CH2SMe | H |
Me | Cl | Br | C(Me)2CH2SMe | H | Cl | Cl | Br | C(Me)2CH2SMe | H |
Me | Cl | Br | Me | Me | Cl | Cl | Br | Me | Me |
Me | Br | F | H | H | Cl | Br | F | H | H |
Me | Br | F | Me | H | Cl | Br | F | Me | H |
Me | Br | F | Et | H | Cl | Br | F | Et | H |
Me | Br | F | i-Pr | H | Cl | Br | F | i-Pr | H |
Me | Br | F | t-Bu | H | Cl | Br | F | t-Bu | H |
Me | Br | F | CH2CN | H | Cl | Br | F | CH2CN | H |
Me | Br | F | CH(Me)CH2SMe | H | Cl | Br | F | CH(Me)CH2SMe | H |
R1 | R2 | R3 | R4 | R5 | R1 | R2 | R3 | R4 | R5 |
Me | Br | F | C(Me)2CH2SMe | H | Cl | Br | F | C(Me)2CH2SMe | H |
Me | Br | F | Me | Me | Cl | Br | F | Me | Me |
Me | Br | Cl | H | H | Cl | Br | Cl | H | H |
Me | Br | Cl | Me | H | Cl | Br | Cl | Me | H |
Me | Br | Cl | Et | H | Cl | Br | Cl | Et | H |
Me | Br | Cl | i-Pr | H | Cl | Br | Cl | i-Pr | H |
Me | Br | Cl | t-Bu | H | Cl | Br | Cl | t-Bu | H |
Me | Br | Cl | CH2CN | H | Cl | Br | Cl | CH2CN | H |
Me | Br | Cl | CH(Me)CH2SMe | H | Cl | Br | Cl | CH(Me)CH2SMe | H |
Me | Br | Cl | C(Me)2CH2SMe | H | Cl | Br | Cl | C(Me)2CH2SMe | H |
Me | Br | Cl | Me | Me | Cl | Br | Cl | Me | Me |
Me | Br | Br | H | H | Cl | Br | Br | H | H |
Me | Br | Br | Me | H | Cl | Br | Br | Me | H |
Me | Br | Br | Et | H | Cl | Br | Br | Et | H |
Me | Br | Br | i-Pr | H | Cl | Br | Br | i-Pr | H |
Me | Br | Br | t-Bu | H | Cl | Br | Br | t-Bu | H |
Me | Br | Br | CH2CN | H | Cl | Br | Br | CH2CN | H |
Me | Br | Br | CH(Me)CH2SMe | H | Cl | Br | Br | CH(Me)CH2SMe | H |
Me | Br | Br | C(Me)2CH2SMe | H | Cl | Br | Br | C(Me)2CH2SMe | H |
Me | Br | Br | Me | Me | Cl | Br | Br | Me | Me |
Me | CF3 | F | H | H | Cl | CF3 | F | H | H |
Me | CF3 | F | Me | H | Cl | CF3 | F | Me | H |
Me | CF3 | F | Et | H | Cl | CF3 | F | Et | H |
Me | CF3 | F | i-Pr | H | Cl | CF3 | F | i-Pr | H |
Me | CF3 | F | t-Bu | H | Cl | CF3 | F | t-Bu | H |
Me | CF3 | F | CH2CN | H | Cl | CF3 | F | CH2CN | H |
Me | CF3 | F | CH(Me)CH2SMe | H | Cl | CF3 | F | CH(Me)CH2SMe | H |
Me | CF3 | F | C(Me)2CH2SMe | H | Cl | CF3 | F | C(Me)2CH2SMe | H |
Me | CF3 | F | Me | Me | Cl | CF3 | F | Me | Me |
Me | CF3 | Cl | H | H | Cl | CF3 | Cl | H | H |
Me | CF3 | Cl | Me | H | Cl | CF3 | Cl | Me | H |
Me | CF3 | Cl | Et | H | Cl | CF3 | Cl | Et | H |
Me | CF3 | Cl | i-Pr | H | Cl | CF3 | Cl | i-Pr | H |
Me | CF3 | Cl | t-Bu | H | Cl | CF3 | Cl | t-Bu | H |
Me | CF3 | Cl | CH2CN | H | Cl | CF3 | Cl | CH2CN | H |
Me | CF3 | Cl | CH(Me)CH2SMe | H | Cl | CF3 | Cl | CH(Me)CH2SMe | H |
Me | CF3 | Cl | C(Me)2CH2SMe | H | Cl | CF3 | Cl | C(Me)2CH2SMe | H |
Me | CF3 | Cl | Me | Me | Cl | CF3 | Cl | Me | Me |
Me | CF3 | Br | H | H | Cl | CF3 | Br | H | H |
Me | CF3 | Br | Me | H | Cl | CF3 | Br | Me | H |
Me | CF3 | Br | Et | H | Cl | CF3 | Br | Et | H |
Me | CF3 | Br | i-Pr | H | Cl | CF3 | Br | i-Pr | H |
Me | CF3 | Br | t-Bu | H | Cl | CF3 | Br | t-Bu | H |
Me | CF3 | Br | CH2CN | H | Cl | CF3 | Br | CH2CN | H |
Me | CF3 | Br | CH(Me)CH2SMe | H | Cl | CF3 | Br | CH(Me)CH2SMe | H |
Me | CF3 | Br | C(Me)2CH2SMe | H | Cl | CF3 | Br | C(Me)2CH2SMe | H |
Me | CF3 | Br | Me | Me | Cl | CF3 | Br | Me | Me |
Me | OCF2H | F | H | H | Cl | OCF2H | F | H | H |
R1 | R2 | R3 | R4 | R5 | R1 | R2 | R3 | R4 | R5 |
Me | OCF2H | F | Me | H | Cl | OCF2H | F | Me | H |
Me | OCF2H | F | Et | H | Cl | OCF2H | F | Et | H |
Me | OCF2H | F | i-Pr | H | Cl | OCF2H | E | i-Pr | H |
Me | OCF2H | F | t-Bu | H | Cl | OCF2H | F | t-Bu | H |
Me | OCF2H | F | CH2CN | H | Cl | OCF2H | F | CH2CN | H |
Me | OCF2H | F | CH(Me)CH2SMe | H | Cl | OCF2H | F | CH(Me)CH2SMe | H |
Me | OCF2H | F | C(Me)2CH2SMe | H | Cl | OCF2H | F | C(Me)2CH2SMe | H |
Me | OCF2H | F | Me | Me | Cl | OCF2H | F | Me | Me |
Me | OCF2H | Cl | H | H | Cl | OCF2H | Cl | H | H |
Me | OCF2H | Cl | Me | H | Cl | OCF2H | Cl | Me | H |
Me | OCF2H | Cl | Et | H | Cl | OCF2H | Cl | Et | H |
Me | OCF2H | Cl | i-Pr | H | Cl | OCF2H | Cl | i-Pr | H |
Me | OCF2H | Cl | t-Bu | H | Cl | OCF2H | Cl | t-Bu | H |
Me | OCF2H | Cl | CH2CN | H | Cl | OCF2H | Cl | CH2CN | H |
Me | OCF2H | Cl | CH(Me)CH2SMe | H | Cl | OCF2H | Cl | CH(Me)CH2SMe | H |
Me | OCF2H | Cl | C(Me)2CH2SMe | H | Cl | OCF2H | Cl | C(Me)2CH2SMe | H |
Me | OCF2H | Cl | Me | Me | Cl | OCF2H | Cl | Me | Me |
Me | OCF2H | Br | H | H | Cl | OCF2H | Br | H | H |
Me | OCF2H | Br | Me | H | Cl | OCF2H | Br | Me | H |
Me | OCF2H | Br | Et | H | Cl | OCF2H | Br | Et | H |
Me | OCF2H | Br | i-Pr | H | Cl | OCF2H | Br | i-Pr | H |
Me | OCF2H | Br | t-Bu | H | Cl | OCF2H | Br | t-Bu | H |
Me | OCF2H | Br | CH2CN | H | Cl | OCF2H | Br | CH2CN | H |
Me | OCF2H | Br | CH(Me)CH2SMe | H | Cl | OCF2H | Br | CH(Me)CH2SMe | H |
Me | OCF2H | Br | C(Me)2CH2SMe | H | Cl | OCF2H | Br | C(Me)2CH2SMe | H |
Me | OCF2H | Br | Me | Me | Cl | OCF2H | Br | Me | Me |
Me | OCH2CF3 | F | H | H | Cl | OCH2CF3 | F | H | H |
Me | OCH2CF3 | F | Me | H | Cl | OCH2CF3 | F | Me | H |
Me | OCH2CF3 | F | Et | H | Cl | OCH2CF3 | F | Et | H |
Me | OCH2CF3 | F | i-Pr | H | Cl | OCH2CF3 | F | i-Pr | H |
Me | OCH2CF3 | F | t-Bu | H | Cl | OCH2CF3 | F | t-Bu | H |
Me | OCH2CF3 | F | CH2CN | H | Cl | OCH2CF3 | F | CH2CN | H |
Me | OCH2CF3 | F | CH(Me)CH2SMe | H | Cl | OCH2CF3 | F | CH(Me)CH2SMe | H |
Me | OCH2CF3 | F | C(Me)2CH2SMe | H | Cl | OCH2CF3 | F | C(Me)2CH2SMe | H |
Me | OCH2CF3 | F | Me | Me | Cl | OCH2CF3 | F | Me | Me |
Me | OCH2CF3 | Cl | H | H | Cl | OCH2CF3 | Cl | H | H |
Me | OCH2CF3 | Cl | Me | H | Cl | OCH2CF3 | Cl | Me | H |
Me | OCH2CF3 | Cl | Et | H | Cl | OCH2CF3 | Cl | Et | H |
Me | OCH2CF3 | Cl | i-Pr | H | Cl | OCH2CF3 | Cl | i-Pr | H |
Me | OCH2CF3 | Cl | t-Bu | H | Cl | OCH2CF3 | Cl | t-Bu | H |
Me | OCH2CF3 | Cl | CH2CN | H | Cl | OCH2CF3 | Cl | CH2CN | H |
Me | OCH2CF3 | Cl | CH(Me)CH2SMe | H | Cl | OCH2CF3 | Cl | CH(Me)CH2SMe | H |
Me | OCH2CF3 | Cl | C(Me)2CH2SMe | H | Cl | OCH2CF3 | Cl | C(Me)2CH2SMe | H |
Me | OCH2CF3 | Cl | Me | Me | Cl | OCH2CF3 | Cl | Me | Me |
Me | OCH2CF3 | Br | H | H | Cl | OCH2CF3 | Br | H | H |
Me | OCH2CF3 | Br | Me | H | Cl | OCH2CF3 | Br | Me | H |
R1 | R2 | R3 | R4 | R5 | R1 | R2 | R3 | R4 | R5 |
Me | OCH2CF3 | Br | Et | H | Cl | OCH2CF3 | Br | Et | H |
Me | OCH2CF3 | Br | i-Pr | H | Cl | OCH2CF3 | Br | i-Pr | H |
Me | OCH2CF3 | Br | t-Bu | H | Cl | OCH2CF3 | Br | t-Bu | H |
Me | OCH2CF3 | Br | CH2CN | H | Cl | OCH2CF3 | Br | CH2CN | H |
Me | OCH2CF3 | Br | CH(Me)CH2SMe | H | Cl | OCH2CF3 | Br | CH(Me)CH2SMe | H |
Me | OCH2CF3 | Br | C(Me)2CH2SMe | H | Cl | OCH2CF3 | Br | C(Me)2CH2SMe | H |
Me | OCH2CF3 | Br | Me | Me | Cl | OCH2CF3 | Br | Me | Me |
Me | OCF3 | F | H | H | Cl | OCF3 | F | H | H |
Me | OCF3 | F | Me | H | Cl | OCF3 | F | Me | H |
Me | OCF3 | F | Et | H | Cl | OCF3 | F | Et | H |
Me | OCF3 | F | i-Pr | H | Cl | OCF3 | F | i-Pr | H |
Me | OCF3 | F | t-Bu | H | Cl | OCF3 | F | t-Bu | H |
Me | OCF3 | F | CH2CN | H | Cl | OCF3 | F | CH2CN | H |
Me | OCF3 | F | CH(Me)CH2SMe | H | Cl | OCF3 | F | CH(Me)CH2SMe | H |
Me | OCF3 | F | C(Me)2CH2SMe | H | Cl | OCF3 | F | C(Me)2CH2SMe | H |
Me | OCF3 | F | Me | Me | Cl | OCF3 | F | Me | Me |
Me | OCF3 | Cl | H | H | Cl | OCF3 | Cl | H | H |
Me | OCF3 | Cl | Me | H | Cl | OCF3 | Cl | Me | H |
Me | OCF3 | Cl | Et | H | Cl | OCF3 | Cl | Et | H |
Me | OCF3 | Cl | i-Pr | H | Cl | OCF3 | Cl | i-Pr | H |
Me | OCF3 | Cl | t-Bu | H | Cl | OCF3 | Cl | t-Bu | H |
Me | OCF3 | Cl | CH2CN | H | Cl | OCF3 | Cl | CH2CN | H |
Me | OCF3 | Cl | CH(Me)CH2SMe | H | Cl | OCF3 | Cl | CH(Me)CH2SMe | H |
Me | OCF3 | Cl | C(Me)2CH2SMe | H | Cl | OCF3 | Cl | C(Me)2CH2SMe | H |
Me | OCF3 | Cl | Me | Me | Cl | OCF3 | Cl | Me | Me |
Me | OCF3 | Br | H | H | Cl | OCF3 | Br | H | H |
Me | OCF3 | Br | Me | H | Cl | OCF3 | Br | Me | H |
Me | OCF3 | Br | Et | H | Cl | OCF3 | Br | Et | H |
Me | OCF3 | Br | i-Pr | H | Cl | OCF3 | Br | i-Pr | H |
Me | OCF3 | Br | t-Bu | H | Cl | OCF3 | Br | t-Bu | H |
Me | OCF3 | Br | CH2CN | H | Cl | OCF3 | Br | CH2CN | H |
Me | OCF3 | Br | CH(Me)CH2SMe | H | Cl | OCF3 | Br | CH(Me)CH2SMe | H |
Me | OCF3 | Br | C(Me)2CH2SMe | H | Cl | OCF3 | Br | C(Me)2CH2SMe | H |
Me | OCF3 | Br | Me | Me | Cl | OCF3 | Br | Me | Me |
表2
R1 | R2 | R3 | R4 | R6 | R1 | R2 | R3 | R4 | R6 |
Me | CF3 | Cl | Me | F | Me | CF3 | Cl | Me | Cl |
Cl | CF3 | Cl | Me | F | Cl | CF3 | Cl | Me | Cl |
Br | CF3 | Cl | Me | F | Br | CF3 | Cl | Me | Cl |
Me | Cl | Cl | Me | F | Me | Cl | Cl | Me | Cl |
Cl | Cl | Cl | Me | F | Cl | Cl | Cl | Me | Cl |
Br | Cl | Cl | Me | F | Br | Cl | Cl | Me | Cl |
Me | Br | Cl | Me | F | Me | Br | Cl | Me | Cl |
Cl | Br | Cl | Me | F | Cl | Br | Cl | Me | Cl |
Br | Br | Cl | Me | F | Br | Br | Cl | Me | Cl |
Me | CF3 | Cl | i-Pr | F | Me | CF3 | Cl | i-Pr | Cl |
Cl | CF3 | Cl | i-Pr | F | Cl | CF3 | Cl | i-Pr | Cl |
Br | CF3 | Cl | i-Pr | F | Br | CF3 | Cl | i-Pr | Cl |
Me | Cl | Cl | i-Pr | F | Me | Cl | Cl | i-Pr | Cl |
Cl | Cl | Cl | i-Pr | F | Cl | Cl | Cl | i-Pr | Cl |
Br | Cl | Cl | i-Pr | F | Br | Cl | Cl | i-Pr | Cl |
Me | Br | Cl | i-Pr | F | Me | Br | Cl | i-Pr | Cl |
Cl | Br | Cl | i-Pr | F | Cl | Br | Cl | i-Pr | Cl |
Br | Br | Cl | i-Pr | F | Br | Br | Cl | i-Pr | Cl |
R1 | R2 | R3 | R4 | R7 | R1 | R2 | R3 | R4 | R7 |
Me | CF3 | F | Me | F | Me | CF3 | Cl | Me | Cl |
Cl | CF3 | F | Me | F | Cl | CF3 | Cl | Me | Cl |
Br | CF3 | F | Me | F | Br | CF3 | Cl | Me | Cl |
R1 | R2 | R3 | R4 | R7 | R1 | R2 | R3 | R4 | R7 |
Me | Cl | F | Me | F | Me | Cl | Cl | Me | Cl |
Cl | Cl | F | Me | F | Cl | Cl | Cl | Me | Cl |
Br | Cl | F | Me | F | Br | Cl | Cl | Me | Cl |
Me | Br | F | Me | F | Me | Br | Cl | Me | Cl |
Cl | Br | F | Me | F | Cl | Br | Cl | Me | Cl |
Br | Br | F | Me | F | Br | Br | Cl | Me | Cl |
Me | CF3 | F | i-Pr | F | Me | CF3 | Cl | i-Pr | Cl |
Cl | CF3 | F | i-Pr | F | Cl | CF3 | Cl | i-Pr | Cl |
Br | CF3 | F | i-Pr | F | Br | CF3 | Cl | i-Pr | Cl |
Me | Cl | F | i-Pr | F | Me | Cl | Cl | i-Pr | Cl |
Cl | Cl | F | i-Pr | F | Cl | Cl | Cl | i-Pr | Cl |
Br | Cl | F | i-Pr | F | Br | Cl | Cl | i-Pr | Cl |
Me | Br | F | i-Pr | F | Me | Br | Cl | i-Pr | Cl |
Cl | Br | F | i-Pr | F | Cl | Br | Cl | i-Pr | Cl |
Br | Br | F | i-Pr | F | Br | Br | Cl | i-Pr | Cl |
配制品/效用
本发明的化合物一般作为包含液体稀释剂、固体稀释剂或表面活性剂至少之一的与农学或非农学适宜的载体的配制品或组合物使用。选择该配制品或组合物组分,使之与有效成分的物理性质、施用方式和环境因素,如土壤类型、湿度和温度相容。有用的配制品包括液体如溶液剂(包括可乳化的浓缩物)、混悬剂、乳剂(包括微乳和/或悬乳(suspoemulsions))等,它们可以任选被浓缩成凝胶。有用的配制品进一步包括固体如药粉(dusts)、散剂、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。可以将有效成分(微)胶囊化并进一步形成混悬剂或固体配制品;或者可以将有效成分的整个配制品胶囊化(或“包衣”)。胶囊化可以控制或延迟有效成分的释放。可喷雾的配制品可以在适宜的介质中提供,使用的喷雾体积为每公顷约一百至几百升。高强度组合物主要用作进一步配制的中间体。
配方通常含有有效量的有效成分、稀释剂和表面活性剂,大约在如下范围内,它们总和为100重量%。
重量百分比 | |||
有效成分 | 稀释剂 | 表面活性剂 | |
水分散性和水溶性颗粒剂、片剂和散剂 | 5-90 | 0-94 | 1-15 |
混悬剂、乳剂、溶液剂(包括可乳化的浓缩物)药粉颗粒剂与丸剂高强度组合物 | 5-501-250.01-9990-99 | 40-9570-995-99.990-10 | 0-150-50-150-2 |
典型的固体稀释剂在Watkins等人,Handbook of Insecticide DustDiluents and Carriers,2nd Ed.,Dorland Books,Caldwell,New Jersey中有描述。典型的液体稀释剂在Marsden,Solvents Guide,2nd Ed.,Interscience,New York,1950中有描述。McCutcheon’s Detergents andEmulsifiers Annual,Allured Publ.Corp.,Ridgewood,New Jersey,以及Sisely和Wood,Encyclopedia of Surface Active Agents,ChemicalPubl.Co.,Inc.,New York,1964列出了表面活性剂和推荐的用途。所有配制品都可以含有少量添加剂以减少泡沫、结块、腐蚀、微生物生长等,或者含有增稠剂以增加粘度。
举例来说,表面活性剂包括聚乙氧基化醇、聚乙氧基化烷基酚、聚乙氧基化脱水山梨糖醇脂肪酸酯、二烷基磺基琥珀酸酯、烷基硫酸酯、烷基苯磺酸酯、有机硅、N,N-二烷基牛磺酸盐、木质素磺酸盐、萘磺酸盐甲醛缩合物、聚羧酸盐和聚氧乙烯/聚氧丙烯嵌段共聚物。举例来说,固体稀释剂包括诸如膨润土、蒙脱石、硅镁土和高岭土的粘土、淀粉、糖、二氧化硅、滑石、硅藻土、尿素、碳酸钙、碳酸钠和碳酸氢钠以及硫酸钠。举例来说,液体稀释剂包括水、N,N-二甲基甲酰胺、二甲基亚砜、N-烷基吡咯烷酮、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、菜籽油和椰子油、脂肪酸酯、诸如环己酮、2-庚酮、异佛乐酮和4-羟基-4-甲基-2-戊酮的酮类,以及诸如甲醇、环己醇、十二烷基醇和四氢呋喃醇的醇类。
溶液剂,包括可乳化的浓缩物,可以简单地通过混合各组分来制备。药粉和散剂可以通过混合,并且通常在锤式粉碎机或流能磨中进行研磨而制备。混悬剂通常通过湿磨而制备;举例来说,参见U.S.3,060,084。颗粒剂和丸剂可以通过将活性物质喷在预制成的颗粒载体上或者通过团聚技术来制备。参见Browning,“Agglomeration”,Chemical Engineering,1967年12月4日,pp 147-48;Perry’s ChemicalEngineer’s Handbook,4th Ed.,McGraw-Hill,New York,1963,pp 8-57和下述的,以及PCT公开WO 91/13546。丸剂的制备如U.S.4,172,714中所描述。水分散性和水溶性颗粒剂可以根据U.S.4,144,050、U.S.3,920,442和DE 3,246,493所教导而制备。片剂可以根据U.S.5,180,587、U.S.5,232,701和U.S.5,208,030所教导而制备。膜剂可以根据GB 2,095,558和U.S.3,299,566所教导而制备。
有关配制技术的更多信息,参见T.S.Woods,“The Formulator’sToolbox-Product Forms for Modem Agriculture”,in PesticideChemistry and Bioscience,The Food-Environment Challenge,T.Brooks和T.R.Roberts,Eds.,Proceedings of the 9th International Congress onPesticide Chemistry,The Royal Society of Chemistry,Cambridge,1999,pp.120-133。另外参见U.S.3,235,361,第6栏第16行至第7栏第19行及实施例10-41;U.S.3,309,192,第5栏第43行至第7栏第62行及实施例8、12、15、39、41、52、53、58、132、138-140、162-164、166、167和169-182;U.S.2,891,855,第3栏第66行至第5栏第17行及实施例1-4;Klingman,Weed Control as a Science,John Wiley andSons,Inc.,New York,1961,pp 81-96;以及Hance等人,Weed ControlHandbook,8th Ed.,Blackwell Scientific Publications,Oxford,1989。
在以下实施例中,所有百分比均以重量计,并且所有配制品都用常规方法制备。化合物号指索引表A中的化合物。
实施例A
可湿性散剂
化合物 165.0%
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%
蒙脱石(煅烧的) 23.0%
实施例B
颗粒剂
化合物 110.0%
硅镁土颗粒(低挥发物,0.71/0.30mm; 90.0%
U.S.S.No.25-50筛)
实施例C
挤压丸
化合物 125.0%
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
可乳化的浓缩物
化合物 120.0%
油溶性磺酸盐和聚氧乙烯醚的混合物 10.0%
异佛乐酮 70.0%
实施例E
颗粒剂
化合物 10.5%
纤维素 2.5%
乳糖 4.0%
玉米粉 93.%
本发明的化合物的特征在于有利的代谢和/或土壤残留模式,并且表现出防治广谱农学和非农学无脊椎动物害虫的活性。本发明的化合物的特征还在于植物中有利的叶和/或土壤施用系统性(systemicity),表现出易位从而保护叶和不与包含本发明的化合物的杀虫组合物直接接触的其它植物部分。(在本发明公开的上下文中,“无脊椎动物害虫防治”指抑制无脊椎动物害虫发育(包括致死性),所述抑制导致摄食或由害虫引起的其他损害或伤害显著减少;相关的表述定义类似。)如本发明公开中所称,术语“无脊椎动物害虫”包括作为害虫具有经济重要性的节肢类、腹足类和线虫类。术语“节肢类”包括昆虫、螨、蜘蛛、蝎、蜈蚣、百足虫、鼠妇和综合纲(symphylans)。术语“腹足类”包括蜗牛、蛞蝓和其他有柱腹足目。术语“线虫类”包括所有蠕虫,如蛔虫、犬心丝虫,以及植食性线虫(线虫纲)、吸虫(吸虫纲(Tematoda))、棘头虫纲和绦虫(多节绦虫亚纲)。本领域技术人员会认识到,并非所有的化合物对所有的害虫有相同的效力。本发明的化合物对具有经济重要性的农学和非农学害虫表现出活性。术语“农学”指大田作物,如食物和纤维的生产,并且包括谷类作物(例如小麦、燕麦、大麦、黑麦、稻、玉蜀黍)、大豆、蔬菜作物(例如莴苣、卷心菜、番茄、豆)、马铃薯、甘薯、葡萄、棉,以及木本果树(例如仁果类、核果类和柑桔类水果)。术语“非农学”指其他的园艺作物(例如不在田间生长的森林、温室、苗圃或观赏植物)、草皮(商用、高尔夫球、住宅、娱乐等等)、木制品、公共卫生(人)和动物健康、家用和商用结构、家用品,以及贮存的产品应用或害虫。由于无脊椎动物害虫防治谱和经济上的重要性,通过防治无脊椎动物害虫保护棉、玉蜀黍、大豆、稻、蔬菜作物、马铃薯、甘薯、葡萄和木本果树农作物(不受由无脊椎动物害虫导致的损害或伤害)是本发明的优选实施方案。农学或非农学害虫包括鳞翅目幼虫,如夜蛾科的栗蚕蛾幼虫、切根虫、尺蠖和heliothines(例如草地粘虫(Spodoptera fugiperda J.E.Smith)、甜菜夜蛾(Spodoptera exigua Hübner)、小地蚕(Agrotis ipilonHufnagel)、粉纹夜蛾(Trichoplusia ni Hübner)、菸夜蛾(Heliothisvirescens Fabricius));螟蛾科的蛀虫、鞘蛾、结网毛虫、coneworms、菜青虫(cabbageworms)和雕叶虫(例如玉米螟(Ostrinia nubilalisHübne)、脐橙螟(Amyelois transitella Walker)、玉米根草螟(Crambuscaliginosellus Clemens)、苍螟(Herpetogramma licarsisalis Walker));卷蛾科的卷叶虫、卷叶蛾、种子蠕虫(seed worms)和果实蠕虫(fruit worms)(例如苹果蠹蛾(Cydia pomonella Linnaeus))、葡萄小食心虫(Endopizaviteana Clemens)、梨小食心虫(Grapholita molesta Busck));以及许多其他具有经济重要性的鳞翅目(例如小菜蛾(Plutella xylostellaLinnaeus)、棉红铃虫(Pectinophora gossypiella Saunders)、舞毒蛾(Lymantria dispar Linnaeus));蟑螂目的幼虫和成虫,包括Blattellidae和蜚蠊科的蟑螂(例如东方蜚蠊(Blatta orientalis Linnaeus)、亚洲蜚蠊(Blatella asahinai Mizukubo)、德国蜚蠊(Blattella germanica Linnaeus)、褐带鲱蠊(Supella longipalpa Fabricius)、美洲栗(Periplaneta americanaLinnaeus)、褐色大蠊(Periplaneta brunnea Burmeister)、马德拉蜚蠊(Leucophaea Maderae Fabricius));鞘翅目的摄叶幼虫和成虫,包括长角象虫科、豆象科和象虫科的象鼻虫(例如棉铃象鼻虫(Anthonomusgrandis Boheman)、稻水象虫(Lissorhoptrus oryzophilus Kuschel)、谷象鼻虫(Sitophilus granarius Linnaeus)、米象鼻虫(Sitophilus oryzaeLinnaeus));叶甲科的跳甲、黄守瓜、食虫(rootworms)、叶甲、薯虫和潜叶虫(例如马铃薯甲虫(Leptinotarsa decemlineata Say)、玉米根叶甲(Diabrotica virgifera LeConte));Scaribaeidae的金龟子和其他甲虫(例如日本丽金龟(Popillia japonica Newman)和欧金龟(Rhizotrogusmajalis Razoumowsky));幼蛀虫科的地毯甲虫;叩头甲科的金针虫;棘胫小蠹科的小蠹和拟步甲科的粉甲虫。另外,农学和非农学害虫包括:革翅目的成虫和幼虫,包括球螋科的蠼螋(例如欧洲蠼螋(Forficulaauricularia Linnaeus)、黑蠼螋(Chelisoches morio Fabricius));半翅目和同翅目的成虫和幼虫,如盲蝽科的盲蝽、蝉科的蝉、大叶蝉科的叶蝉(例如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、盾蚧科和绵蚧科的介壳虫(scales)、网蝽科的网蝽、蝽科的蝽象、长蝽科的麦长蝽(例如Blissus spp.)和其他Lygaeidae科的实蝽、沫蝉科的沫蝉、缘蝽科的南瓜缘蝽,以及红蝽科的红椿和棉红蝽。作为农学和非农学害虫还包括螨目的成虫和幼虫,如叶螨科的蛛螨和红蜘蛛(例如欧洲红蜘蛛(Panonychus ulmi Koch)、红蜘蛛(Tetranychus urticae Koch)、McDaniel螨(Tetranychus mcdanieliMcGregor))、毛足蛛科(Tenuipalpidae)的flat mite(例如桔短须螨(Brevipalpus lewisi McGregor))、瘿螨科的桔叶刺瘿螨和bud mites,以及其他摄叶螨和在人和动物健康方面重要的螨,即Epidermoptidae科的粉螨、蠕螨科的毛囊蠕形螨、Glycyphagidae科的干酪螨;硬蜱目的蜱(例如鹿蜱(Ixodes scapulars Say)、澳大利亚麻痹蜱(Ixodesholocyclus Neumann)、美洲犬蜱(Dermacentor variabilis Say)、美洲花蜱(Amblyomma americanum Linnaeus)和Psoroptidae、蒲螨科和疥螨科的痂螨和疥螨;直翅目的成虫和幼虫,包括蚱蜢、蝗虫和蟋蟀(例如迁徙蚱蜢(例如Melanoplus sanguinipes Fabricius、M.differentialisThomas)、美洲蚱蜢(例如Schistocerca americana Drury)、沙漠蝗(Schistocerca gregaria Forskal)、迁徙蝗虫(Locusta migratoriaLinnaeus)、灌木蝗虫(Zonocerus spp.)、家蟋蟀(Acheta domesticusLinnaeus)、蝼蛄(Gryllotalpa spp.));双翅目的成虫和幼虫,包括潜叶虫、蠓、果蝇(实蝇科)、瑞典杆蝇(例如Oscinella.frit Linnaeus)、土壤蛆(soil maggots)、房屋蝇(例如Musca domestica Linnaeus)、较小房屋蝇(例如Fannia canicularis Linnaeus,F.femoralis Stein)、厩螫蝇(例如Stomoxys calcitrans Linnaeus)、面蝇、螫蝇、blow蝇(例如Chrysomyaspp.、Phormia spp.),以及其他蝇状飞行害虫、马虻(例如Tabanus spp.)、肤蝇类幼虫(例如Gastrophilus spp.、Oestrus spp.)、牛皮蝇(例如Hypoderma spp.)、鹿虻(例如Chrysops spp.)、羊蜱蝇(例如Melophagusovinus Linnaeus)及其他Brachycera、蚊子(例如Aedes spp.、Anophelesspp.、Culex spp.)、墨蚊(例如Prosimulium spp.、Simulium spp.)、蠓、毛蠓、sciarids,以及其他长角亚目;缨翅目的成虫和幼虫,包括葱蓟马(Thrips tabaci Lindeman)、花蓟马(Frankliniella spp.)和其他摄叶蓟马;膜翅目的昆虫害虫,包括蚂蚁(例如锈色大黑蚁(Camponotusferrugineus Fabricius)、黑木蚁(Camponotus pennsylvanicus De Geer)、厨蚁(Monomorium pharaonis Linnaeus)、小火蚁(Wasmanniaauropunctata Roger)、火蚁(Solenopsis geminate Fabricius)、外引红火蚁(Solenopsis invicta Buren)、阿根廷蚁(Iridomyrmex humilis Mayr)、家褐蚁(Paratrechina longicornis Latreille)、铺道蚁(Tetramoriumcaespitum Linnaeus)、玉米田蚁(Lasius alienus Frster)、香家蚁(Tapinoma sessile Say)、蜜蜂(包括木蜂)、大胡蜂、胡蜂、黄蜂和叶蜂(Neodiprion spp.、Cephus spp.);等翅目昆虫害虫,包括东方地下白蚁(Reticulitermes flavipes Kollar)、西方犀白蚁(Reticulitermes hesperusBanks)、台湾家白蚁(Coptotermes formosanus Shiraki)、西印度干木白蚁(incistermes immigrans Snyder)和其他具有经济重要性的白蚁;缨尾亚目的昆虫害虫,如蠹虫(Lepisma saccharina Linnaeus)和家衣鱼(Thermobia domestica Packard);禽虱目的昆虫害虫,包括头虱(Pediculus humanus capitis De Geer)、体虱(Pediculus humanus humanusLinnaeus)、鸡体虱(Menacanthus stramineus Nitszch)、狗羽虱(Trichodectes canis De Geer)、鸡姬虱(Goniocotes gallinae De Geer)、羊体虱(Bovicola ovis Schrank)、短鼻牛虱(Haematopinus eurysternusNitzsch)、长鼻牛虱(Linognathus vituli Linnaeus)以及其他攻击人和动物的吸和咀嚼寄生虱;Siphonoptera目的昆虫害虫,包括东方鼠蚤(Xenopsylla cheopis Rothschild)、猫栉头蚤(Ctenocephalides felisBouche)、狗栉头蚤(Ctenocephalides canis Curtis)、母鸡跳蚤(Ceratophyllus gallinae Schrank)、禽毒蚤(Echidnophaga gallinaceaWestwood)、人蚤(Pulex irritans Linnaeus)和其他困扰哺乳动物和鸟类的蚤。所涵盖的其他无脊椎动物害虫包括:蜘蛛目的蜘蛛,如褐皮花蛛(Loxosceles reclusa Gertsch & Mulaik)和黑寡妇毒蛛(Latrodectusmactans Fabricius),以及Scutigeromorpha目的蜈蚣,如家蚰蜒(Scutigera coleoptrata Linnaeus)。本发明的化合物还对线虫纲、多节绦虫亚纲、吸虫纲和棘头虫纲的成员,包括圆线虫目(Strongylida)、蛔总目(Ascaridida)、尖尾目(Oxyurida)、小杆目、旋尾目和嘴刺目的具有经济重要性的成员具有活性,例如但不限于具有经济重要性的农学昆虫(即根结线虫(Meloidogyne)属的根癌线虫、短体线虫(Pratylenchus)属的根斑线虫、毛刺线虫属(Trichodorus)的粗短根线虫等),以及动物和人健康害虫(即所有具有经济重要性的吸虫、绦虫和蛔虫,如马中的Strongylus vulgaris、狗中的Toxocara canis、羊中的Haemonchus contortus、狗中的Dirofilaria immitis Leidy、马中的Anoplocephala perfoliata、反刍动物中的Fasciola hepatica Linnaeus等)。
本发明的化合物对以下害虫具有特别高的活性:鳞翅目(例如棉叶波纹夜蛾(Alabama argillacea Hübner)、果黄卷蛾(Archipsargyrospila Walker)、欧洲卷蛾(A.rosana Linnaeus)和其他黄卷蛾(Archips)种、二化螟(Chilo suppressalis Walker)、稻纵卷叶螟(Cnaphalocrosis medinalis Guenee)、玉米根草螟(Crambuscaliginosellus Clemens)、早熟禾草螟(Crambus teterrellus Zincken)、苹果蠹蛾(Cydia pomonella Linnaeus)、鼎点金刚钻(Earias insulanaBoisduval)、埃及金刚钻(Earias vittella Fabricius)、美国螟蛉虫(Helicoverpa armigera Hübner)、玉米穗蛾(Helicoverpa zea Boddie)、菸夜蛾(Heliothis virescens Fabricius)、苍螟(Herpetogramma licarsisalisWalker)、葡萄小食心虫(Lobesia botrana Denis & Schiffermüller)、棉红铃虫(Pectinophora gossypiella Saunders)、桔细潜蛾(Phyllocnistiscitrella Stainton)、大菜粉蝶(Pieris brassicae Linnaeus)、小菜粉蝶(Pierisrapae Linnaeus)、小菜蛾(Plutella xylostella Linnaeus)、甜菜夜蛾(Spodoptera exigua Hübner)、斜纹夜蛾(Spodoptera litura Fabricius)、草地粘虫(Spodoptera frugiperda J.E.Smith)、粉纹夜蛾(Trichoplusia niHübner)和tomato leafminer(Tuta absoluta Meyrick))。本发明的化合物对同翅目的成员也具有商业上重要的活性,所述同翅目包括:豌豆蚜(Acyrthisiphon pisum Harris)、豇豆蚜(Aphis craccivora Koch)、蚕豆蚜(Aphis fabae Scopoli)、棉蚜(Aphis gossypii Glover)、苹蚜(Aphis pomi DeGeer)、锈线菊蚜(Aphis spiraecola Patch)、指顶花无网蚜(Aulacorthumsolani Kaltenbach)、草莓中瘤钉毛蚜(Chaetosiphon fragaefoliiCockerell)、俄罗斯麦长管蚜(Diuraphis noxia Kurdjumov/Mordvilko)、车前圆尾蚜(Dysaphis plantaginea Paaserini)、苹绵蚜(Eriosomalanigerum Hausmann)、桃大尾蚜(Hyalopterus pruni Geoffroy)、芜菁蚜(Lipaphis erysimi Kaltenbach)、谷蚜(Metopolophium dirrhodumWalker)、马铃薯长管蚜(Macrosipum euphorbiae Thomas)、桃蚜(Myzuspersicae Sulzer)、莴苣衲长管蚜(Nasonovia ribisnigri Mosley)、根蚜和葡糖根疣蚜(Pemphigus spp.)、玉米蚜(Rhopalosiphum maidis Fitch)、bird cherry-oat aphid(Rhopalosiphum padi Linnaeus)、麦二叉蚜(Schizaphis graminum Rondani)、麦长管蚜(Sitobion avenae Fabricius)、苜蓿斑蚜(Therioaphis maculata Buckton)、桔声蚜(Toxoptera aurantiiBoyer de Fonscolombe)和热带桔二岔蚜(Toxoptera citricida Kirkaldy);球蚜(Adelges spp);美核桃根瘤蚜(Phylloxera devastatrix Pergande);烟草粉虱(Bemisia tabaci Gennadius)、甘薯粉虱(Bemisia argentifoliiBellows & Perring)、柑桔粉虱(Dialeurodes citri Ashmead)和温室粉虱(Trialeurodes vaporariorum Westwood);马铃薯微叶蝉(Empoascafabae Harris)、小褐稻虱(Laodelphax striatellus Fallen)、六点叶蝉(Macrolestes quadrilineatus Forbes)、茶微叶蝉(Nephotettix cinticepsUhler)、黑尾叶蝉(Nephotettix nigropictus Stl)、稻褐飞虱(Nilaparvatalugens Stl)、玉米蜡蝉(Peregrinus maidis Ashmead)、白背稻虱(Sogatella furcifera Horvath)、美洲稻飞虱(Sogatodes orizicola Muir)、苹白小叶蝉(Typhlocyba pomaria McAtee)、葡糖斑叶蝉(Erythroneouraspp.);期蝉(Magicidada septendecim Linnaeus)、吹绵蚧(Lcerya purchasiMaskell);梨圆盾蚧(Quadraspidiotus perniciosus Comstock);柑桔粉蚧(Planococcus citri Risso);其他粉蚧复合体(Pseudococcus spp.);梨黄木虱(Cacopsylla pyricola Foerster)、柿木虱(Trioza diospyri Ashmead)。这些化合物还对半翅目的成员有活性,所述半翅目包括:稻绿蝽(Acrosternum hilare Say)、南瓜绿蝽(Anasa tristis De Geer)、麦长蝽(Blissus leucopterus leucopterus Say)、棉网蝽(Corythuca gossypiiFabricius)、番茄蝽(Cyrtopeltis modesta Distant)、棉黑翅红蝽(Dysdercussuturellus Herrich-Schffer)、褐臭蝽(Euchistus servus Say)、一点褐蝽(Euchistus variolarius Palisot de Beauvois)、地长蝽属(Graptosthetusspp)、松籽喙缘蝽(Leptoglossus corculus Say)、牧草盲蝽(Lyguslineolaris Palisot de Beauvois)、稻绿蝽(Nezara viridula Linnaeus)、稻褐蝽(Oebalus pugnax Fabricius)、大马利筋长蝽(Oncopeltus fasciatusDallas)、棉跳盲蝽(Pseudatomoscelis seriatus Reuter)。由本发明的化合物防治的其他昆虫目包括缨翅目(例如苜蓿蓟马(Frankliniellaoccidentalis Pergande)、桔实蓟马(Scirthothrips citri Moulton)、大豆蓟马(Sericothrips variabilis Beach)和葱蓟马(Thrips tabaci Lindeman)),以及鞘翅目(例如马铃薯甲虫(Leptinotarsa decemlineata Say)、墨西哥豆瓢虫(Epilachna varivestis Mulsant)和Agriotes、Athous或Limonius属的金针虫)。
本发明的化合物还可以与一种或多种其他生物学活性化合物或活性剂,包括杀虫剂、杀真菌剂、杀线虫剂、杀菌剂、杀螨剂、生长调节剂如生根刺激剂、化学不育剂、半化学药物(semiochemical)、拒虫剂、诱虫剂、外激素、取食刺激剂、其他生物活性化合物或昆虫致病细菌、病毒或真菌混合,以形成多组分杀虫药,所述杀虫药给出更宽的农业和非农业效用谱。因此,本发明还涉及一种组合物,其包含生物学有效量的式I的化合物以及有效量的至少一种附加生物学活性化合物或活性剂,并且可以进一步包含至少一种表面活性剂、固体稀释剂或液体稀释剂。这些可与本发明的化合物一起配制的生物学活性化合物或活性剂的实例为:杀虫剂如阿维菌素、乙酰甲胺磷、吡虫清、acetoprole、amidoflument(S-1955)、齐墩螨素、艾扎丁、谷硫磷、氟氯菊酯、联苯肼酯、双三氟虫脲(bistrifluron)、噻嗪酮、呋喃丹、氟唑虫清、定虫隆、毒死蜱、甲基毒死蜱、环虫酰肼(chromafenozide)、噻虫胺、百树菊酯、β-氟氯氰菊酯、氯氟氰菊酯、λ-氯氟氰菊酯、氯氰菊酯、灭蝇胺、溴氰菊酯、杀螨硫隆、二嗪农、氟脲杀、乐果、呋虫胺(dinotefuran)、噁茂醚、依马菌素、硫丹、高氰戊菊酯、乙虫清(ethiprole)、苯硫威、双氧威、甲氰菊酯、杀灭菊酯、锐劲特、flonicamid、氟氰戊菊酯、氟胺氰菊酯、flufenerim(UR-50701)、氟虫脲、γ-chalothrin、特丁苯酰肼、氟铃脲、吡虫啉、噁二唑虫、丙胺磷、氟丙氧脲、马拉硫磷、蜗牛敌、甲胺磷、杀扑磷、灭多虫、蒙五一五、甲氧滴滴涕、甲氧苯酰肼、甲氧苄氟菊酯(metofluthrin)、久效磷、甲氧苯酰肼、双苯氟脲、noviflumuron(XDE-007)、甲氨叉威、对硫磷、甲基对硫磷、氯菊酯、甲拌磷、伏杀磷、亚胺硫磷、磷胺、抗蚜威、丙溴磷、丙氟菊酯(profluthrin)、protrifenbute、拒嗪酮、pyridalyl、蚊蝇醚、鱼藤酮、S1812(Valent)艾克敌105、spiromesifin(BSN 2060)、乙丙硫磷、双苯酰肼、伏虫隆、七氟菊酯、特丁磷、杀虫畏、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)、硫双灭多威、杀虫双、tolfenpyrad、四溴菊酯、敌百虫和杀虫隆;杀真菌剂,如噻二唑素、甲基硫、腈嘧菌酯、benalazy-M、苯噻菌胺(benthiavalicarb)、苯菌灵、灭瘟素、波尔多液(碱式硫酸铜)、boscalid、糠菌唑、粉病定、氯环丙酰胺、敌菌丹、克菌丹、多菌灵、地茂散、百菌清、克霉清、王铜、铜盐、清菌脲、cyazofamid、cyflufenamid、环唑醇、环丙嘧啶、双氯氰菌胺(diclocymet)、哒菌清、氯硝胺、噁咪唑、烯酰吗啉、dimoxystrobin、烯唑醇、烯唑醇-M、多果定、克瘟散、氧唑菌、ethaboxam、噁唑酮菌、异嘧菌醇、腈苯唑、fenhexamid、fenoxanil、拌种咯、苯锈啶、丁苯吗啉、薯瘟锡、毒菌锡、氟啶胺、氟噁菌、氟联苯菌、fluoxastroin、喹唑菌酮、氟硅唑、氟酰胺、粉唑醇、灭菌丹、藻菌磷、呋氨丙灵、呋吡唑灵(furametapyr)、双胍辛乙酸盐(guazatine)、己唑醇、土菌消、烯菌灵、酰胺唑、双胍辛乙酸盐(iminoctadine)、环戊唑醇、异稻瘟净、异丙定、iprovalicarb、异康唑(Isoconazole)、稻瘟灵、春雷霉素、亚胺菌、代森锰锌、代森锰、mefenoxam、mepanapyrim、丙氧灭绣胺、甲霜灵、环戊唑菌、叉氨苯酰胺、metrafenone、micronazole、腈菌唑、田安甲胂铁(甲基胂酸铁)、氟苯嘧啶醇、oryzastrobin、噁霜灵、噁咪唑(oxpoconazole)、戊菌唑、戊菌隆、picobenzamid、啶氧菌酯(picoxystrobin)、噻菌灵、丙氯灵、百维灵、丙环唑、proquinazid、prothioconazole、pyraclostrobin、二甲嘧菌胺、啶斑肟、咯喹酮、喹氧灵、silthiofam、硅氟唑(simeconazole)、sipconazole、螺噁茂胺、硫、戊唑醇、氟醚唑、tiadinil、涕必灵、溴氟唑菌、甲基托布津、福美双、对甲抑菌灵、三唑酮、唑菌醇、嘧菌醇、三环唑、肟菌酯(trifloxystrobin)、戊叉唑菌、嗪氨灵、戊叉唑菌、烯效唑、有效霉素、烯菌酮和zoxamide;杀线虫剂如涕灭威、甲氨叉威和克线磷;杀菌剂如链霉素;杀螨剂如虫螨脒、灭螨猛、乙酯杀螨醇、三环锡、三氯杀螨醇、除螨灵、特苯噁唑、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;以及生物试剂,如苏云金芽孢杆菌(Bacillusthuringiensis),包括鲇泽亚种(ssp.Aizawai)和库尔斯塔克亚种(kurstaki),苏云金芽孢杆菌δ-内毒素、杆状病毒,以及昆虫致病细菌、病毒和真菌。本发明的化合物及其组合物可以施用于经遗传转变以表达对无脊椎动物害虫有毒的蛋白(如苏云金芽孢杆菌毒素)的植物。外源施用的本发明的无脊椎动物害虫防治化合物的作用可以是与表达的毒素蛋白协同的。
有关这些农用保护剂的通用参考文献是The Pesticide Manual,12th Ed.,C.D.S.Tomlin,Ed.,British Crop Protection Council,Farnham,Surrey,U.K.,2000。
用于与本发明的化合物混合的优选杀虫剂和杀螨剂包括拟除虫菊酯类如吡虫清、氯氰菊酯、氯氟氰菊酯、百树菊酯、β-氟氯氰菊酯、高氰戊菊酯、杀灭菊酯和四溴菊酯;氨基甲酸酯类如苯硫威、灭多虫、甲氨叉威和硫双灭多威;新烟碱类(neonicotinoids)如噻虫胺、吡虫啉和噻虫啉;神经钠通道阻滞剂如噁二唑虫;杀虫大环内酯如艾克敌105、阿维菌素、齐墩螨素和依马菌素;γ-氨基丁酸(GABA)拮抗剂如硫丹、ethiprole和锐劲特;杀虫脲类如氟虫脲和杀虫隆;保幼激素模拟物如噁茂醚和蚊蝇醚;拒嗪酮;和虫螨脒。用于与本发明的化合物混合的优选生物试剂包括苏云金芽孢杆菌和苏云金芽孢杆菌δ-内毒素,以及天然存在的和遗传改良的病毒杀虫剂,包括杆状病毒科的成员和昆虫致病真菌。
最优选的混合物包括本发明的化合物与氯氟氰菊酯的混合物;本发明的化合物与β-氟氯氰菊酯的混合物;本发明的化合物与高氰戊菊酯的混合物;本发明的化合物与甲氨叉威的混合物;本发明的化合物与吡虫啉的混合物;本发明的化合物与噻虫啉的混合物;本发明的化合物与噁二唑虫的混合物;本发明的化合物与阿维菌素的混合物;本发明的化合物与硫丹的混合物;本发明的化合物与乙虫清的混合物;本发明的化合物与锐劲特的混合物;本发明的化合物与氟虫脲的混合物;本发明的化合物与蚊蝇醚的混合物;本发明的化合物与拒嗪酮的混合物;本发明的化合物与虫螨脒的混合物;本发明的化合物与苏云金芽孢杆菌鲇泽亚种或苏云金芽孢杆菌库尔斯塔克亚种的混合物,和本发明的化合物与苏云金芽孢杆菌δ-内毒素的混合物。
在某些情况中,与具有相似防治谱但具有不同作用模式的其他无脊椎动物害虫防治化合物或试剂的组合对于耐药性管理特别有利。因此,本发明的组合物可以进一步包含生物学有效量的至少一种具有相似防治谱但具有不同作用模式的附加无脊椎动物害虫防治化合物或试剂。使遗传改良成表达植物保护化合物(例如蛋白)的植物或者该植物的场所与生物学有效量的本发明的化合物接触还提供广谱的植物保护并且对于耐药性管理有利。
通过向包括农学和/或非农学的受侵染场所、向要保护的区域或者直接对要防治的害虫施用有效量的一种或多种本发明的化合物而在农学或非农学应用中防治无脊椎动物害虫。因此,本发明进一步包括在农学和/或非农学应用中防治无脊椎动物的方法,其包括使无脊椎动物或其环境与生物学有效量的一种或多种本发明的化合物接触,或者与包含至少一种这种化合物的组合物接触,或者与包含至少一种这种化合物和至少一种有效量的附加生物学活性化合物或活性剂的组合物接触。包含本发明的化合物和有效量的至少一种附加生物学活性化合物或活性剂的适宜组合物的实例包括颗粒组合物,其中该附加生物学活性化合物与本发明的化合物存在于同一颗粒上,或者与本发明的化合物存在于不同的颗粒上。
优选的接触方法是喷雾。或者,可以将包含本发明的化合物的颗粒组合物施用于植物叶片或土壤。通过使植物与包含本发明的化合物的组合物接触,本发明的化合物还有效地通过植物吸收而递送,所述组合物作为土壤浸液液体配制品或用于土壤的颗粒配制品、苗圃箱处理剂或移植苗浸液而施用。通过向受侵染场所局部施用包含本发明的化合物的组合物,这些化合物也有效。其他接触方法包括通过直接和滞留喷洒、航空喷洒、凝胶剂、种衣、微胶囊化、内吸吸收、饵料、耳标、大药丸、烟雾发生器、熏蒸剂、烟雾剂、药粉和许多其他方法来施用本发明的化合物或组合物。还可以将本发明的化合物浸入制造无脊椎动物防治装置(例如昆虫网)的材料中。
可以将本发明的化合物掺入被无脊椎动物害虫食用的饵料组合物中,或者在诸如捕捉阱、饵料仓等装置内使用。这种饵料组合物可以是颗粒的形式,其包含(a)有效成分,即式I的化合物、其N-氧化物或盐,(b)一种或多种食物材料,任选的(c)诱虫剂,和任选的(d)一种或多种湿润剂。值得注意的是,包含约0.001-5%的有效成分、约40-99%的食物材料和/或诱虫剂和任选的约0.05-10%的湿润剂的颗粒或饵料组合物在非常低的施药量下,特别是在通过摄入而非直接接触而致死的有效成分剂量下,在防治土壤无脊椎动物害虫有效。值得注意的是,某些食物材料既起食物源的作用又起诱虫剂的作用。食物材料包括糖类、蛋白质和脂类。食物材料的实例是植物粉、糖、淀粉、动物脂、植物油、酵母抽提物和乳固体。诱虫剂的实例是臭气物质和增香剂,如果实或植物提取物、香料或其他动物或植物组分、信息素或已知吸引目标无脊椎动物害虫的其他试剂。湿润剂,即保湿剂的实例是乙二醇和其他多元醇、甘油和山梨糖醇。值得注意的是用于防治无脊椎动物害虫,单独或组合包括蚂蚁、白蚁和蟑螂的饵料组合物(和这种饵料组合物的使用方法)。用于防治无脊椎动物害虫的装置可以包括本发明的饵料组合物和适于接收该饵料组合物的外壳,其中该外壳具有至少一个开孔,其大小允许该无脊椎动物害虫通过该开孔,使该无脊椎动物害虫可以从该外壳以外的位置接近该饵料组合物,并且其中该外壳进一步适于放在该无脊椎动物害虫可能或已知的活动场所中或附近。
本发明的化合物可以以其纯态施用,但是最通常的施用是包含一种或多种化合物与适宜的载体、稀释剂和表面活性剂的配制品,并且根据预期的最终用途该配制品可能包含食物。优选的施用方法包括喷洒该化合物的水分散液或精炼油溶液。与喷淋油、喷淋油浓缩物、粘展剂、辅剂、其他溶剂和诸如胡椒基丁醚的增效剂组合经常提高化合物功效。对于非农学用途,可以通过泵,或者通过从加压容器,例如加压气雾剂喷射罐中释放的方法,从喷雾容器,如罐、瓶或其他容器中施用这种喷雾剂。这些喷雾组合物可以采取各种形式,例如雾状物、烟雾、泡沫、烟或雾。因此这些喷雾组合物可以进一步视情况包含抛射剂、起泡剂等。值得注意的是包含本发明的化合物或组合物和抛射剂的喷雾组合物。代表性的抛射剂包括,但不限于甲烷、乙烷、丙烷、异丙烷、丁烷、异丁烷、丁烯、戊烷、异戊烷、新戊烷、戊烯、氢氟烃(hydrofluorocarbons)、氯氟烃(chlorofluoroacarbons)、二甲醚和前述化合物的混合物。值得注意的是用于防治无脊椎动物害虫,单独或组合包括蚊子、墨蚊、厩螫蝇、鹿虻、马虻、黄蜂、胡蜂、大胡蜂、壁虱、蜘蛛、蚂蚁、蚋等的喷雾组合物(以及这种从喷雾器施予的喷雾组合物的使用方法)。
有效防治所需的施药量(即“生物学有效量”)取决于要防治的无脊椎动物物种、害虫的生活周期、生活期、其大小、位置、一年的时间、寄主作物或动物、摄食行为、交配行为、环境湿度、温度等因素。在正常环境下,每公顷约0.01-2kg有效成分的施药量足以在农学生态系统中防治害虫,但是小至0.0001kg/公顷的施药量可能是足够的,或者可能需要高达8kg/公顷的施药量。对于非农学应用,有效的施药量为约1.0-5.0mg/m2,但是小至0.1mg/m2可能是足够的,或者可能需要高达150mg/m2。本领域技术人员可以容易地确定所需无脊椎动物害虫防治水平所必需的生物学有效量。
以下测试表明本发明的化合物对特定害虫的防治功效。“防治功效”表示引起摄食显著减少的无脊椎动物害虫发育抑制(包括致死性)。但是,该化合物所提供的害虫防治保护并不限于这些物种。参阅化合物说明的索引表A、B和C。在索引表中使用以下缩写:i是异,t是叔,Me是甲基,Et是乙基,Pr是丙基,i-Pr是异丙基,c-Pr是环丙基,Bu是丁基,并且CN是氰基。缩写“Ex”代表“实施例”,并且由其后的数字表明该化合物在哪个实施例中制备。
索引表A
化合物 | R1 | R2 | R3 | R4 | R5 | 熔点(℃) |
1(Ex.1) | Me | CF3 | Cl | H | H | 200-202 |
2(Ex.2) | Me | CF3 | Cl | Me | H | 214-216 |
3(Ex.3) | Me | Cl | Cl | Me | H | * |
4(Ex.4) | Me | Cl | Cl | H | H | >255 |
5(Ex.5) | Me | Br | Cl | Me | H | * |
6(Ex.6) | Me | Br | Cl | H | H | >255 |
7(Ex.7) | Cl | Cl | Cl | Me | H | 197-200 |
8 | Me | CF3 | Cl | i-Pr | H | >250 |
9 | Cl | Cl | Cl | i-Pr | H | 213-215 |
10 | Cl | Br | Cl | i-Pr | H | 222-225 |
11 | Cl | Br | Cl | i-Pr | Me | 224-226 |
12 | Cl | Br | Cl | Me | H | 198-201 |
13 | Cl | Cl | Cl | i-Pr | Me | 238-241 |
14 | Cl | Br | Cl | H | H | >255 |
15 | Cl | F | Cl | i-Pr | H | 162-166 |
16 | Cl | F | Cl | Me | H | 205-208 |
17 | Cl | Br | F | i-Pr | H | 230-232 |
18 | Cl | Br | F | Me | H | * |
19 | Cl | Br | F | H | H | >255 |
20 | Me | CF3 | Cl | Me | Me | 227-230 |
化合物 | R1 | R2 | R3 | R4 | R5 | 熔点(℃) |
21 | Cl | CF3 | Cl | i-Pr | H | 247-249 |
22 | Cl | CF3 | Cl | Me | H | 215-217 |
23 | Cl | CF3 | Cl | H | H | >255 |
24 | Me | Cl | Cl | i-Pr | H | * |
25 | Me | Br | Cl | i-Pr | H | * |
26 | Me | Cl | Cl | CH2CN | H | 213-215 |
27 | Me | Br | Cl | CH2CN | H | 225-227 |
28 | Me | OCH2CF3 | Cl | Me | Me | 132-135 |
29 | Me | OCH2CF3 | Cl | Me | H | 162-165 |
30 | Me | CF3 | Cl | t-Bu | H | >250 |
31 | Me | CF3 | Cl | CH2CN | H | 250-251 |
32 | Me | CF3 | Cl | Et | H | 150-151 |
33 | Me | Cl | Cl | Et | H | * |
34 | Me | Cl | Cl | t-Bu | H | >255 |
35 | Me | Br | Cl | Et | H | * |
36 | Me | Br | Cl | t-Bu | H | >255 |
37 | Me | CF3 | Cl | CH(CH3)CH2SMe | H | 208-209 |
39 | Me | Br | Cl | Me | Me | 262-264 |
40 | Me | OCH2CF3 | Cl | i-Pr | H | 164-167 |
41 | Me | OCH2CF3 | Cl | t-Bu | H | * |
42 | Me | OCH2CF3 | Cl | Me | Me | 212-214 |
43 | Me | OCH2CF3 | Cl | Et | H | 168-171 |
44 | Me | OCH2CF3 | Cl | CH2CN | H | 207-211 |
45 | Me | Cl | Cl | Me | Me | 261-263 |
46 | Me | CF3 | F | Me | H | 211-212 |
47 | Me | CF3 | F | H | H | 138-139 |
48 | Me | CF3 | F | Et | H | 219-220 |
49 | Me | Br | F | Me | H | 152-153 |
50 | Me | Br | F | H | H | 162-164 |
51 | Me | Br | F | Et | H | 201-202 |
52 | Me | CF3 | F | i-Pr | H | 229-230 |
53 | Me | Br | F | i-Pr | H | 159-160 |
54 | Me | CF3 | F | CH(CH3)CH2SMe | H | 209-210 |
55 | F | Br | Cl | Me | H | 209-210 |
63 | Me | Br | Cl | CH(CH3)CH2SMe | H | 180-181 |
64 | Me | Cl | Cl | CH(CH3)CH2SMe | H | 193-194 |
65 | Me | Br | Cl | C(CH3)2CH2SMe | H | 161-162 |
化合物 | R1 | R2 | R3 | R4 | R5 | 熔点(℃) |
66 | Me | CF3 | Cl | C(CH3)2CH2SMe | H | 250-250 |
67 | Me | Cl | Cl | C(CH3)2CH2SMe | H | 234-235 |
68 | Me | CF3 | Cl | c-Pr | H | 159-160 |
69 | Me | CF3 | Cl | (CH2)2OMe | H | 206-207 |
70 | Me | Cl | Cl | c-Pr | H | 156-157 |
71 | Me | Cl | Cl | (CH2)2OMe | H | 118-119 |
72 | Me | Br | Cl | (CH2)2OMe | H | 216-217 |
73 | Me | Br | Cl | c-Pr | H | 159-160 |
74 | Me | CF3 | Cl | Me | H | 235-236 |
75 | Me | CF3 | Cl | CH2CH(CH3)2 | H | 257-258 |
76 | Me | Br | Cl | CH2(c-Pr) | H | 223-224 |
77 | Me | Br | Cl | CH2CH(CH3)2 | H | 245-246 |
78 | Me | Br | Cl | CH(CH3)CH2S(O)Me | H | 157-158 |
79 | Me | Br | Cl | CH(CH3)CH2S(O)2Me | H | 169-170 |
80 | Me | Cl | Cl | CH(CH3)(CH2)2SMe | H | 190-191 |
81 | Me | Br | Cl | CH(CH3)(CH2)2SMe | H | 188-190 |
82 | Me | CF3 | Cl | CH(CH3)(CH2)2SMe | H | 134-135 |
83 | Me | Cl | Cl | CH(CH3)(CH2)2S(O)2Me | H | 186-187 |
84 | Me | Br | Cl | CH(CH3)(CH2)2S(O)2Me | H | 182-183 |
85 | Br | Br | Cl | Me | H | 214-215 |
86 | Br | Br | Cl | i-Pr | H | 166-167 |
87 | Br | Br | Cl | CH2CN | H | 226-227 |
88 | Me | Cl | F | Me | H | 149-150 |
89 | Me | Cl | F | H | H | 146-147 |
90 | Me | Cl | Br | H | H | 189-190 |
91 | Me | Cl | Br | Me | H | 149-150 |
92 | Me | Cl | Br | i-Pr | H | 119-120 |
93 | Me | Cl | Br | Me | Me | 247-248 |
94 | Me | Br | Br | H | H | 255-256 |
95 | Me | Br | Br | Me | H | 183-184 |
96 | Me | Br | Br | i-Pr | H | 235-236 |
97 | Me | Br | Br | Me | Me | 242-243 |
*1H NMR数据参阅索引表C。
索引表B
化合物 | R1 | R2 | R3 | R4 | R5 | R6 | R7 | 熔点(℃) |
98 | Me | Br | Cl | Me | H | H | Cl | 145-146 |
99 | Me | Br | Cl | Et | H | H | Cl | 148-149 |
100 | Me | Br | Cl | i-Pr | H | H | Cl | 174-175 |
101 | Me | Cl | Cl | Et | H | H | Cl | 167-168 |
102 | Me | Cl | Cl | i-Pr | H | H | Cl | 189-190 |
103 | Me | Cl | Cl | Me | H | H | Cl | 185-186 |
104 | Me | Br | Cl | Me | H | F | H | 152-153 |
105 | Me | Br | Cl | i-Pr | H | F | H | 134-136 |
106 | Me | Cl | F | H | H | H | F | 212-213 |
107 | Me | Cl | F | Me | H | H | F | 214-215 |
108 | Me | Br | F | H | H | H | F | 204-205 |
109 | Me | Br | F | Me | H | H | F | 222-223 |
110 | Me | Br | F | Et | H | H | F | 200-201 |
111 | Me | Br | F | i-Pr | H | H | F | 203-204 |
112 | Me | Cl | F | Et | H | H | F | 195-196 |
索引表C
化合物号 | 1H NMR数据(除非另有说明,均为CDCl3溶液)a |
3 | (CDCl3)10.55(s,1H),8.45(d,1H),7.85(dd,1H),7.55(s,2H),7.40(dd,1H),6.97(s,1H),6.30(b q,1H),2.98(d,3H),2.24(s,3H) |
5 | (CDCl3)10.55(s,1H),8.45(d,1H),7.85(dd,1H),7.57(m,2H),7.37(dd,1H),7.05(s,1H),6.30(b q,1H),2.98(d,3H),2.24(s,3H) |
18 | (CDCl3)10.10(brs,1H),8.38(d,1H),7.75(s,1H),7.65(s,1H),7.60(m,1H),7.34(m,1H),7.10(s,1H),6.58(b q,1H),2.96(s,3H) |
24 | (CDCl3)10.12(s,1H),8.56(d,1H),7.85(d,1H),7.58(m,2H),7.40(dd,1H),6.97(s,1H),6.00(b d,1H),4.22(m,1H),2.25(s,3H),1.26(d,6H) |
25 | (CDCl3)10.60(s,1H),8.47(d,1H),7.85(dd,1H),7.56(s,2H),7.39(dd,1H),7.06(s,1H),6.04(b d,1H),4.20(m,1H),2.24(s,3H),1.26(s,6H) |
33 | (CDCl3)10.60(s,1H),8.45(d,1H),7.85(d,1H),7.58(s,2H),7.39(m,1H),6.97(s,1H),6.20(b t,1H),3.46(m,2H),2.25(s,3H),1.25(t,3H) |
35 | (CDCl3)10.60(s,1H),8.46(d,1H),7.85(d,1H),7.57(s,2H),7.38(m,1H),7.05(s,1H),6.25(b t,1H),3.46(m,2H),2.24(s,3H),1.25(t,3H) |
41 | (CDCl3)10.40(s,1H),8.47(d,1H),7.85(d,1H),7.50(s,2H),7.37(dd,1H),6.63(s,1H),5.97(s,1H),4.68(q,2H),1.42(s,9H) |
本发明的生物学实施例
测试A
为了评价小菜蛾(Plutella xylostella)的防治,试验装置由小的开口容器组成,其内部有12-14天大的萝卜植物。通过使用心土采样器从一片其上生长了许多幼虫的变硬的昆虫食物中取出一块(a plug)并且将含有幼虫和食物的该块转移至该试验装置,用一片昆虫食物上的10-15只新生幼虫预先侵染之。随着该食物块干透,幼虫被转移到测试植物上。
使用含有10%丙酮、90%水和300ppm含烷芳基聚氧乙烯、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(Loveland Industries,Inc.Greeley,Colorado,USA)的溶液来配制测试化合物。通过放置在每个试验装置顶部上方1.27cm(0.5英寸)的带有1/8JJ定制主体的SUJ2喷嘴(Spraying Systems Co.Wheaton,Illinois,USA)来施用1mL所配制的化合物的液体。在这些测试中,所有测试化合物均喷洒50ppm的,并且重复三次。在喷洒所配制的测试化合物后,将每个试验装置干燥1小时,然后在上面放置黑色遮蔽盖(creened cap)。将试验装置在生长室中于25℃和70%相对湿度下保持6天。然后根据被食用的叶片视觉评价植物摄食损害。
在所测试的化合物中,以下化合物提供非常好至极好水平的植物保护(20%或更低摄食损害):1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25、26、27、28、29、30、31、32、33、34、35、36、37、38、39、40、41、42、43、44、45、46、47、48、49、50、51、52、53、54、63、64、65、66、67、68、69、70、71、72、73、74、75、76、77、78、79、80、81、82、83、84、88、89、90、91、92、94、95、96、97、98、99、100、101、102、103、106、108、109、110、111和112。
测试B
为了评价草地粘虫(Spodoptera frugiperda)的防治,试验装置由小的开口容器组成,其内部有4-5天大的玉米(玉蜀黍)植物。(使用心土采样器)用在一片昆虫食物上的10-15只1天大的幼虫预先侵染之。
如测试A所述,配制并喷洒50ppm的测试化合物。施用重复三次。在喷洒后,在生长室中保持试验装置,然后如测试A所述视觉评价等级。
在所测试的化合物中,以下化合物提供极好水平的植物保护(20%或更低摄食损害):1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、20、21、22、24、25、26、27、28、29、30、31、32、33、34、35、36、37、38、39、40、41、42、43、44、45、46、47、48、49、50、51、52、53、54、55、56、63、64、65、66、67、68、70、73、74、76、78、88、91、92、94、95、96、98、99、100、101、102、103、106、109、110、111和112。
测试C
为了评价通过接触和/或内吸方法进行的桃蚜(Myzus persicae)的防治,试验装置由小的开口容器组成,其内部有12-15天大的萝卜植物。通过在测试植物的叶片上放置在剪自培养植物的一片叶子上的30-40只蚜虫来预先侵染之(切叶方法)。随着叶片变干,该幼虫被转移到测试植物上。在预先侵染后,用一层砂覆盖该试验装置的土壤。
使用含有10%丙酮、90%水和300ppm含烷芳基聚氧乙烯、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(Loveland Industries,Inc.)的溶液来配制测试化合物。通过放置在每个试验装置顶部上方1.27cm(0.5英寸)的带有1/8JJ定制主体的SUJ2喷嘴(Spraying Systems Co.)来施用1mL所配制的化合物的液体。在本筛选中,所有测试化合物均喷洒250ppm,重复三次。在喷洒所配制的测试化合物后,将每个试验装置干燥1小时,然后在顶部放置黑色遮蔽盖。将该试验装置在生长室中于19-21℃和50-70%相对湿度下保持6天。然后视觉评价每个试验装置的昆虫死亡率。
在所测试的化合物中,以下化合物导致至少80%的死亡率:1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25、26、27、28、29、30、31、32、33、34、35、36、37、38、40、41、43、44、46、47、48、49、50、51、52、53、55、56、63、65、66、67、68、69、70、73、74、76、78、88、89、90、91、92、94、95、96、98、99、100、101、102、103、106、108、109、110、111和112。
测试D
为了评价通过接触和/或内吸方法进行的马铃薯微叶蝉(Empoasca fabae Harris)的防治,试验装置由小的开口容器组成,其内部有5-6天大的Longio豆植物(出现初生叶)。向土壤的顶部添加白砂并且在施用前剪下一片初生叶。如测试C所述,配制并喷洒250ppm的测试化合物,并且重复三次。在喷洒后,将试验装置干燥1小时,然后用5只马铃薯微叶蝉(18至21天大的成虫)后感染(post-infest)。在柱体的顶部放置黑色遮蔽盖。将该试验装置在生长室中于19-21℃和50-70%的相对湿度下保持6天。然后视觉评价每个试验装置的昆虫死亡率。
在所测试的化合物中,以下化合物导致至少80%的死亡率:1、3、4、5、6、8、10、12、16、17、18、19、20、21、22、23、24、25、26、27、28、29、32、33、34、35、37、38、40、41、43、44、46、47、48、49、50、51、52、53、54、55、56、63、66、67、68、70、73、76、88、89、90、94、95、98、99、101、103、106、108、109、110、111和112。。
测试E
为了评价通过接触和/或内吸方法进行的棉蚜(Aphis gossypii)的防治,试验装置由小的开口容器组成,其内部有6-7天大的棉花植物。根据测试C所述的切叶法,用在一片叶子上的30-40只昆虫预先侵染之,用一层砂覆盖试验装置的土壤。
如测试D所述,配制并喷洒250ppm的测试化合物。施用重复三次。在喷洒后,在生长室中保持试验装置,然后如测试D所述视觉评价等级。
在所测试的化合物中,以下化合物导致至少80%的死亡率:1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、24、25、26、27、28、29、32、33、34、35、36、37、38、39、40、41、42、43、44、46、47、48、49、50、51、52、53、55、56、63、69、71、72、74、76、78、79、81、84、88、89、90、91、92、95、96、97、98、99、100、101、102、103、106、108、109、110、111和112。
测试F
为了评价通过接触和/或内吸方法进行的玉米蜡蝉(Peregrinusmaidis)的防治,试验装置由小的开口容器组成,其内部有3-4天大的谷物(玉蜀黍)植物(穗状花序)。施用前向土壤上面添加白砂。如测试C所述,配制并喷洒250ppm的测试化合物,并且重复三次。在喷洒后,将试验装置干燥1小时,然后用10-20只玉米蜡蝉(18至20天大的成虫)通过将它们用盐瓶洒到砂上来对试验装置进行后侵染。在柱体的顶部放置黑色遮蔽盖。将试验装置在生长室中于19-21℃和50-70%的相对湿度下保持6天。然后视觉评价每个试验装置的昆虫死亡率。
在所测试的化合物中,以下化合物导致至少80%的死亡率:1、2、3、4、5、6、7、8、10、11、12、13、18、20、24、25、26、27、28、29、32、33、35、37、38、39、40、41、43、45、46、47、48、49、50、51、53、56、88、89、90、91、94、95、108和109。
测试G
为了评价银叶粉虱(Bemisia tabaci)的防治,试验装置由生长在Redi-earth培养基(Scotts Co.)中的14-21天大的棉花植物组成,所述棉花植物具有至少两片真叶在叶子下侧被第二和第三龄蛹侵染。
将测试化合物配制在不超过2mL丙酮中,然后用水稀释至25-30mL。用平扇空气辅助喷嘴(Spraying Systems 122440)在10psi(69kPa)下施用所配制的化合物。喷洒植物,以在转盘喷雾器上进行试验。本筛选中的所有测试化合物均喷洒250ppm,并且重复三次。在喷洒测试化合物后,将试验装置在生长室中于50-60%的相对湿度和白天28℃,晚上24℃的温度下保持6天。然后转移叶子,计数死亡和存活的蛹以计算百分死亡率。
在所测试的化合物中,以下化合物导致至少80%的死亡率:2、3、4、5、7、8、9、10、24、25、26、27、28、30、32、33、34、35、38、41、46、48、49、51、52、53、66、67、70、73、88、92和98。
测试H
为了评价化合物叶运动通过植物后,化合物在植物中的运动和桃蚜(Myzus persicae)和马铃薯微叶蝉(Empoasca fabae)的防治,试验装置由小的开口容器组成,其内部有12-15天大的萝卜植物(对于桃蚜测试)或5-6天大的Longio豆植物(用于马铃薯微叶蝉测试)。
使用含有10%丙酮、90%水和600ppm含烷芳基聚氧乙烯、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(Loveland Industries,Inc.)的溶液来配制测试化合物。通过吸量管向两片较大的光合活性的叶子上施用20μL所配制的化合物。在本筛选中,所有测试化合物均施用1000ppm,并且测试重复三次。在喷洒所配制的测试化合物后,在每个实验装置的土壤上覆盖一层砂,并将每个试验装置干燥1小时,然后在顶部放置黑色遮蔽盖。将试验装置保持在约20℃和50-70%相对湿度的生长室中。
2天后,在经处理的叶片所有面上覆盖细塑料网,但是叶柄部分是完整的,仍连接在植物上,以使导管运动和光合作用正常。然后用20-30只蚜虫(萝卜)或20只叶蝉(大豆)侵染植物,并在生长室中再保持8天。然后视觉评价每个试验装置在未经处理的植物上接触和喂养的昆虫的死亡率。
桃蚜死亡率(% GPAM)结果和马铃薯微叶蝉死亡率(% PLHM)结果列于表A中。
表A
化合物 | %PLHM | %GPAM |
134562627 | 58969396777313 | 878178941006757 |
测试I
为了评价化合物从土壤施用通过茎到达叶的木质部运动后,化合物在植物中的运动和桃蚜(Myzus persicae)和马铃薯微叶蝉(Empoascafabae)的防治,试验装置由小的开口容器组成,其内部有12-15天大的萝卜植物(对于桃蚜测试)或5-6天大的Longio豆植物(对于马铃薯微叶蝉测试)。
使用含有10%丙酮、90%水和600ppm含烷芳基聚氧乙烯、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(Loveland Industries,Inc.)的溶液来配制测试化合物。通过吸量管向植物基部的土壤施用1mL所配制的化合物的溶液。在本筛选中,所有测试化合物均喷洒1000ppm,并且测试重复三次。在施用所配制的测试化合物后,将每个试验装置干燥1小时。将每个试验装置的土壤覆盖一层砂,然后在顶部放置黑色遮蔽盖。将试验装置保持在约20℃和50-70%相对湿度的生长室中。
2天后,然后用20-30只蚜虫(萝卜)或20只叶蝉(大豆)侵染植物,并在生长室中再保持5天。然后视觉评价每个试验装置的在未处理的植物叶片上接触和喂养的昆虫的死亡率。
桃蚜死亡率(% GPAM)结果和马铃薯微叶蝉死亡率(% PLHM)结果列于表B中。
表B
昆虫百分死亡率 | ||
化合物 | %PLHM | %GPAM |
1256 | 1005695100 | 64644059 |
权利要求书
(按照条约第19条的修改)
11.权利要求8或权利要求9的方法,其中该无脊椎动物害虫是蚊子、墨蚊、厩螫蝇、鹿虻、马虻、黄蜂、胡蜂、大胡蜂、壁虱、蜘蛛、蚂蚁或蚋,其通过从喷雾器施予的包含该化合物的喷雾组合物而接触。
12.喷雾组合物,其包含:
(a)权利要求1的化合物;和
(b)抛射剂。
13.饵料组合物,其包含:
(a)权利要求1的化合物;
(b)一种或多种食物材料;
(c)任选的诱虫剂;和
(d)任选的湿润剂。
14.用于防治无脊椎动物害虫的装置,其包括:
(a)权利要求13的饵料组合物;和
(b)适于接收该饵料组合物的外壳,其中该外壳具有至少一个开孔,其大小允许该无脊椎动物害虫通过该开孔,使该无脊椎动物害虫可以从该外壳以外的位置接近该饵料组合物,并且其中该外壳进一步适于放在该无脊椎动物害虫可能或已知的活动场所中或附近。
15.权利要求9的方法,其中使植物与作为土壤浸液液体配制品施用的组合物接触。
16.权利要求4的组合物,其为土壤浸液液体配制品的形式。
Claims (14)
2.权利要求1的化合物,其中
R1为Me或Cl;
R2为Cl、Br、CF3、OCF2H、OCF3或OCH2CF3;且
R4为H、Me、Et、i-Pr、t-Bu、CH2CN、CH(Me)CH2SMe或C(Me)2CH2SMe。
3.权利要求2的化合物,其中
R2为Cl、Br、CF3或OCH2CF3;
R4为H、Me、Et或i-Pr;且
R5为H
4.用于防治无脊椎动物害虫的组合物,其包含生物学有效量的权利要求1的化合物和至少一种选自表面活性剂、固体稀释剂和液体稀释剂的附加组分,所述组合物任选进一步包含有效量的至少一种附加生物学活性化合物或活性剂。
5.权利要求4的组合物,其中所述至少一种附加生物学活性化合物或活性剂选自下组杀虫剂:拟除虫菊酯、氨基甲酸酯、新烟碱类、神经元钠通道阻滞剂、杀虫大环内酯、γ-氨基丁酸(GABA)拮抗剂、杀虫脲、保幼激素模拟物、苏云金芽孢杆菌(Bacillus thuringiensis)的一员、苏云金芽孢杆菌δ-内毒素和天然存在的或遗传改良的病毒杀虫剂。
6.权利要求4的组合物,其中该至少一种附加生物学活性化合物或活性剂选自阿维菌素、乙酰甲胺磷、吡虫清、acetoprole、amidoflumet(S-1955)、齐墩螨素、艾扎丁、谷硫磷、氟氯菊酯、联苯肼酯、双三氟虫脲、噻嗪酮、呋喃丹、氟唑虫清、定虫隆、毒死蜱、甲基毒死蜱、环虫酰肼、噻虫胺、百树菊酯、β-氟氯氰菊酯、氯氟氰菊酯、λ-氯氟氰菊酯、氯氰菊酯、灭蝇胺、溴氰菊酯、杀螨硫隆、二嗪农、氟脲杀、乐果、呋虫胺、噁茂醚、依马菌素、硫丹、高氰戊菊酯、乙虫清、苯硫威、双氧威、甲氰菊酯、杀灭菊酯、锐劲特、flonicamid、氟氰戊菊酯、氟胺氰菊酯、flufenerim(UR-50701)、氟虫脲、γ-chalothrin、特丁苯酰肼、氟铃脲、吡虫啉、噁二唑虫、丙胺磷、氟丙氧脲、马拉硫磷、蜗牛敌、甲胺磷、杀扑磷、灭多虫、蒙五一五、甲氧滴滴涕、甲氧苯酰肼、甲氧苄氟菊酯、久效磷、甲氧苯酰肼、双苯氟脲、noviflumuron(XDE-007)、甲氨叉威、对硫磷、甲基对硫磷、氯菊酯、甲拌磷、伏杀磷、亚胺硫磷、磷胺、抗蚜威、丙溴磷、丙氟菊酯、protrifenbute、拒嗪酮、pyridalyl、蚊蝇醚、鱼藤酮、S1812(Valent)艾克敌105、spiromesifen(BSN 2060)、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、tolfenpyrad、四溴菊酯、敌百虫和杀虫隆、涕灭威、克线磷、虫螨脒、灭螨猛、乙酯杀螨醇、三环锡、三氯杀螨醇、除螨灵、特苯噁唑、喹螨醚、杀螨锡、唑螨酯、噻螨酮、克螨特、哒螨酮、吡螨胺、苏云金芽孢杆菌鲇泽亚种(Bacillus thuringiensis aizawai)、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensis kurstaki)、苏云金芽孢杆菌δ-内毒素、杆状病毒、昆虫致病细菌、昆虫致病病毒和昆虫致病真菌。
7.权利要求4的组合物,其中该至少一种附加生物学活性化合物或活性剂选自吡虫清、氯氰菊酯、氯氟氰菊酯、百树菊酯和β-氟氯氰菊酯、高氰戊菊酯、杀灭菊酯、四溴菊酯、苯硫威、灭多虫、甲氨叉威、硫双灭多威、噻虫胺、吡虫啉、噻虫啉、噁二唑虫、艾克敌105、阿维菌素、齐墩螨素、依马菌素、硫丹、乙虫清、锐劲特、氟虫脲、杀虫隆、噁茂醚、蚊蝇醚、拒嗪酮、虫螨脒、苏云金芽孢杆菌鲇泽亚种、苏云金芽孢杆菌库尔斯塔克亚种、苏云金芽孢杆菌δ-内毒素和食虫真菌。
8.用于防治无脊椎动物害虫的方法,其包括使该无脊椎动物害虫或其环境与生物学有效量的权利要求1的化合物接触。
9.用于防治无脊椎动物害虫的方法,其包括使该无脊椎动物害虫或其环境与生物学有效量的权利要求4的组合物接触。
10.权利要求8或权利要求9的方法,其中该无脊椎动物害虫是蟑螂、蚂蚁或白蚁,其通过食用包含该化合物的饵料组合物而与该化合物接触。
11.权利要求8或权利要求9的方法,其中该无脊椎动物害虫是蚊子、墨蚊、厩螫蝇、鹿虻、马虻、黄蜂、胡蜂、大胡蜂、壁虱、蜘蛛、蚂蚁或蚋,其通过从喷雾器施予的包含该化合物的喷雾组合物而接触。
12.喷雾组合物,其包含:
(a)权利要求1的化合物;和
(b)抛射剂。
13.饵料组合物,其包含:
(a)权利要求1的化合物;
(b)一种或多种食物材料;
(c)任选的诱虫剂;和
(d)任选的湿润剂。
14.用于防治无脊椎动物害虫的装置,其包括:
(a)权利要求13的饵料组合物;和
(b)适于接收该饵料组合物的外壳,其中该外壳具有至少一个开孔,其大小允许该无脊椎动物害虫通过该开孔,使该无脊椎动物害虫可以从该外壳以外的位置接近该饵料组合物,并且其中该外壳进一步适于放在该无脊椎动物害虫可能或已知的活动场所中或附近。
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CN113331198B (zh) * | 2021-06-28 | 2023-12-12 | 海利尔药业集团股份有限公司 | 氟氯虫双酰胺用于改善植物品质的用途 |
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