CN116804010A - 具有含硫取代基的杀有害生物活性杂环衍生物 - Google Patents
具有含硫取代基的杀有害生物活性杂环衍生物 Download PDFInfo
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- CN116804010A CN116804010A CN202310706472.8A CN202310706472A CN116804010A CN 116804010 A CN116804010 A CN 116804010A CN 202310706472 A CN202310706472 A CN 202310706472A CN 116804010 A CN116804010 A CN 116804010A
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- alkyl
- methyl
- haloalkyl
- compound
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- 229910052717 sulfur Inorganic materials 0.000 title claims description 7
- 125000001424 substituent group Chemical group 0.000 title description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title description 9
- 125000000623 heterocyclic group Chemical group 0.000 title description 7
- 239000011593 sulfur Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 262
- -1 stereoisomers Chemical class 0.000 claims abstract description 86
- 150000003839 salts Chemical class 0.000 claims abstract description 69
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 44
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims description 126
- 239000000203 mixture Substances 0.000 claims description 94
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 53
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 49
- 241000244206 Nematoda Species 0.000 claims description 42
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical class 0.000 claims description 36
- 241000238631 Hexapoda Species 0.000 claims description 29
- 241000607479 Yersinia pestis Species 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 24
- 125000001153 fluoro group Chemical group F* 0.000 claims description 23
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 15
- 125000004770 (C1-C4) haloalkylsulfanyl group Chemical group 0.000 claims description 13
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 241000237852 Mollusca Species 0.000 claims description 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 4
- 239000002917 insecticide Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 164
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
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- 238000002360 preparation method Methods 0.000 description 46
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- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 34
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- 239000004480 active ingredient Substances 0.000 description 31
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 30
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 28
- 239000007787 solid Substances 0.000 description 27
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- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 24
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- 239000002585 base Substances 0.000 description 23
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
- 241000193388 Bacillus thuringiensis Species 0.000 description 20
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
- 229940097012 bacillus thuringiensis Drugs 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 20
- 229910052938 sodium sulfate Inorganic materials 0.000 description 20
- 235000011152 sodium sulphate Nutrition 0.000 description 20
- 241000238876 Acari Species 0.000 description 19
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 229910052786 argon Inorganic materials 0.000 description 18
- 239000012267 brine Substances 0.000 description 18
- 229910052698 phosphorus Inorganic materials 0.000 description 18
- 239000011574 phosphorus Substances 0.000 description 18
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
- 239000013058 crude material Substances 0.000 description 17
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 16
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- 239000002671 adjuvant Substances 0.000 description 16
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- 239000011734 sodium Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 241000237858 Gastropoda Species 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 15
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- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 13
- 238000001816 cooling Methods 0.000 description 13
- JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 13
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Abstract
具有式(I)的化合物,其中这些取代基是如在权利要求1中所定义的,以及那些化合物的农用化学上可接受的盐、立体异构体、对映异构体、互变异构体和N‑氧化物,可以用作杀昆虫剂并且可按照本身已知的方式制备。
Description
本申请是发明名称为“具有含硫取代基的杀有害生物活性杂环衍生物”的中国发明专利申请201880013060.3的分案申请,其申请日是2018年02月16日,优先权日是2017年02月21日。
本发明涉及含硫取代基的杀有害生物活性(尤其是杀昆虫活性)杂环衍生物,涉及用于制备那些化合物的中间体,涉及包含那些化合物的组合物,并且涉及它们用于控制动物有害生物(包括节肢动物并且尤其是昆虫或蜱螨目的代表)的用途。
具有杀有害生物作用的杂环化合物是已知的并描述于例如WO 2012/086848、WO2013/018928和WO 2016/026848。
现在已经出人意料地发现,某些具有含硫的苯基和吡啶基取代基的新型杀有害生物活性杂环6/5-二环衍生物作为杀有害生物剂具有有利的特性。
因此本发明提供了具有式I的化合物
其中
A是CH或N;
X是S、SO或SO2;
R1是C1-C4烷基、C1-C4卤代烷基或C3-C6环烷基-C1-C4烷基;
G1是N或CH;
X1是O、S或NR3;其中R3是氢或C1-C4烷基;
R2是卤素、C1-C6卤代烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基或C1-C6卤代烷氧基;
R7是氢、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基;以及
R8是卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基;以及具有式I的化合物的农用化学上可接受的盐、立体异构体、对映异构体、互变异构体和N-氧化物。
具有至少一个碱性中心的具有式I的化合物可以与以下酸形成例如酸加成盐,这些酸为:例如强无机酸(例如矿物酸,例如高氯酸、硫酸、硝酸、亚硝酸、磷酸或氢卤酸),强有机羧酸(例如未经取代的或像被卤素取代的C1-C4烷羧酸,例如乙酸(像饱和或不饱和的二羧酸),例如草酸、丙二酸、琥珀酸、马来酸、富马酸或邻苯二甲酸(像羟基羧酸),例如抗坏血酸、乳酸、苹果酸、酒石酸或柠檬酸,或像苯甲酸),或有机磺酸(例如未经取代的或像被卤素取代的C1-C4烷-或芳基磺酸,例如甲烷-或对甲苯磺酸)。具有至少一个酸性基团的具有式I的化合物可以例如与碱形成盐,例如矿物盐,例如碱金属或碱土金属盐,例如钠盐、钾盐或镁盐;或与氨或有机胺形成盐,例如吗啉、哌啶、吡咯烷、单、二或三低碳数烷基胺,例如乙胺、二乙胺、三乙胺或二甲基丙基胺,或单、二或三羟基低碳数烷基胺,例如单乙醇胺、二乙醇胺或三乙醇胺。
在取代基定义中出现的烷基基团可以是直链的或支链的,并且是例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、戊基、己基、壬基、癸基以及它们的支链异构体。烷基硫烷基、烷基亚磺酰基、烷基磺酰基、烷氧基、烯基和炔基基团衍生自所提及的烷基基团。烯基和炔基基团可以是单不饱和的或多不饱和的。
卤素通常是氟、氯、溴或碘。相应地,这也适用于与其他含义结合的卤素,例如卤代烷基或卤代苯基。
卤代烷基基团优选地具有从1至6个碳原子的链长。卤代烷基是例如氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、2,2,2-三氟乙基、2-氟乙基、2-氯乙基、五氟乙基、1,1-二氟-2,2,2-三氯乙基、2,2,3,3-四氟乙基以及2,2,2-三氯乙基。
烷氧基基团优选地具有一个优选的从1至6个碳原子的链长。烷氧基是例如甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基和叔丁氧基并且还是同分异构的戊氧基以及己氧基基团。
烷氧基烷基基团优选地具有1个至6个碳原子的链长。
烷氧基烷基是,例如甲氧基甲基、甲氧基乙基、乙氧基甲基、乙氧基乙基、正丙氧基甲基、正丙氧基乙基、异丙氧基甲基或异丙氧基乙基。
这些环烷基基团优选地具有从3至6个环碳原子,例如环丙基、环丁基、环戊基和环己基。
自由基表示甲基基团。
根据本发明的具有式I的化合物还包括在盐形成期间可能形成的水合物。
R1、R2、X、R7、R8、A、G1以及X1的优选值是以其任何组合如以下列出的:
优选地,R1是C1-C4烷基或C3-C6环烷基-C1-C4烷基。
更优选地,R1是C1-C4烷基或环丙基甲基。
甚至更优选地,R1是甲基、乙基、正丙基、异丙基或环丙基甲基。
最优选地,R1是乙基。
优选地,R2是卤素、C1-C4卤代烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基。
更优选地,R2是卤素或C1-C3卤代烷基。
甚至更优选地,R2是C1-C2卤代烷基。
最优选地,R2是三氟甲基。
优选地,X是S或SO2。
最优选地,X是SO2。
优选地,R7是氢、氟、氰基、C1-C4烷氧基羰基、C1-C4烷基。
更优选地,R7是氢、甲基、乙基或氟。
甚至更优选地,R7是甲基或氟。
最优选地,R7是甲基。
优选地,R8是氰基、氟或C1-C4烷基。
更优选地,R8是氟、甲基或乙基。
甚至更优选地,R8是氟或甲基。
最优选地,R8是甲基。
优选地,A是N。
优选地,G1是N。
优选地,X1是NR3,其中R3是C1-C4烷基。
最优选地,X1是NCH3。
如以下列出的提供了根据本发明所述的实施例。
实施例1提供了如上文所定义的具有式I的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物。
实施例2提供了根据实施例1所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R1是C1-C4烷基或C3-C6环烷基-C1-C4烷基。
实施例3提供了根据实施例1或2所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R2是卤素、C1-C4卤代烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基。
实施例4提供了根据实施例1、2或3中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中X是S或SO2。
实施例5提供了根据实施例1、2、3或4中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R7是氢、氟、氰基、C1-C4烷氧基羰基、C1-C4烷基。
实施例6提供了根据实施例1、2、3、4或5中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R8是氰基、氟或C1-C4烷基。
实施例7提供了根据实施例1、2、3、4、5或6中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中X1是NR3,其中R3是C1-C4烷基。
实施例8提供了根据实施例1、2、3、4、5、6或7中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R1是C1-C4烷基或环丙基甲基。
实施例9提供了根据实施例1、2、3、4、5、6、7或8中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R2是卤素或C1-C3卤代烷基。
实施例10提供了根据实施例1、2、3、4、5、6、7、8或9中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R7是氢、甲基、乙基或氟。
实施例11提供了根据实施例1、2、3、4、5、6、7、8、9或10中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R8是氟、甲基或乙基。
实施例12提供了根据实施例1、2、3、4、5、6、7、8、9、10或11中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中X1是NCH3。
实施例13提供了根据实施例1、2、3、4、5、6、7、8、9、10、11或12中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R1是甲基、乙基、正丙基、异丙基或环丙基甲基。
实施例14提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12或13中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R2是C1-C2卤代烷基。
实施例15提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13或14中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中X是SO2。
实施例16提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14或15中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R7是甲基或氟。
实施例17提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15或16中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R8是氟或甲基。
实施例18提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16或17中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R1是乙基。
实施例19提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17或18中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R2是三氟甲基。
实施例20提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18或19中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R7是甲基。
实施例21提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19或20中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R8是甲基。
实施例22提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20或21中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中A是CH。
实施例23提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20或21中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中A是N。
实施例24提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22或23中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中G1是N。
实施例25提供了根据实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22或23中任一项所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中G1是CH。
具有式I的化合物的一个组是由具有式I-1的化合物表示
其中A、X、R1、R2、R7、和R8是如上文在式I下所定义的。在具有式I-1的化合物的所述优选的组中,
R1优选是甲基、乙基、正丙基、异丙基或环丙基甲基;
R2优选是C1-C4卤代烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基;以及X优选是SO2。
尤其优选的具有式I-1的化合物是以下那些,其中R1是乙基,并且X是SO2。
具有式I-1的化合物的一个组是由具有式I-1a的化合物表示
其中X、R1、R2、R7、和R8是如上文在式I下所定义的。在具有式I-1的化合物的所述优选的组中,
R1优选是甲基、乙基、正丙基、异丙基或环丙基甲基;
R2优选是C1-C4卤代烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基;以及X优选是SO2。
尤其优选的具有式I-1a的化合物是以下那些,其中R1是乙基,并且X是SO2。
具有式I-1的化合物的另一个组是由具有式I-1b的化合物表示
其中X、R1、R2、R7、和R8是如上文在式I下所定义的。在具有式I-1的化合物的所述优选的组中,
R1优选是甲基、乙基、正丙基、异丙基或环丙基甲基;
R2优选是C1-C4卤代烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基;以及X优选是SO2。
尤其优选的具有式I-1b的化合物是以下那些,其中R1是乙基,并且X是SO2。
具有式I的化合物的另一个组是由具有式I-2的化合物表示
其中A、X、R1、R2、R7、和R8是如上文在式I下所定义的。在具有式I-1的化合物的所述优选的组中,
R1优选是甲基、乙基、正丙基、异丙基或环丙基甲基;
R2优选是C1-C4卤代烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基;以及X优选是SO2。
尤其优选的具有式I-2的化合物是以下那些,其中R1是乙基,并且X是SO2。
具有式I-2的化合物的一个组是由具有式I-2a的化合物表示
其中X、R1、R2、R7、和R8是如上文在式I下所定义的。在具有式I-1的化合物的所述优选的组中,
R1优选是甲基、乙基、正丙基、异丙基或环丙基甲基;
R2优选是C1-C4卤代烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基;以及X优选是SO2。
尤其优选的具有式I-2a的化合物是以下那些,其中R1是乙基,并且X是SO2。
具有式I-2的化合物的另一个组是由具有式I-2b的化合物表示
其中X、R1、R2、R7、和R8是如上文在式I下所定义的。在具有式I-1的化合物的所述优选的组中,
R1优选是甲基、乙基、正丙基、异丙基或环丙基甲基;
R2优选是C1-C4卤代烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基;以及X优选是SO2。
尤其优选的具有式I-2b的化合物是以下那些,其中R1是乙基,并且X是SO2。
根据本发明所述的化合物可以具有任何数量的益处,尤其包括针对保护植物对抗昆虫的有利水平的生物活性或对于用作农用化学品活性成分的优越特性(例如,更高的生物活性、有利的活性谱、增加的安全性、改进的物理-化学特性、或增加的生物可降解性)。具体而言,现在已经出人意料地发现某些具有式(I)的化合物相对于非靶标节肢动物特别是传粉者(例如蜜蜂、独居蜂和熊蜂)可以显示出有利的安全性。最尤其地,相对于意大利蜂(Apis mellifera)。
在另一个方面,本发明提供了一种组合物,该组合物包含杀昆虫、杀螨、杀线虫、或杀软体动物有效量的如在实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24或25(如上)中任一项或具有式(I-1)、(I-1a)、(I-1b)、(I-2)、(I-2a)和(I-2b)的化合物的实施例(如上)中任一项所定义的具有式(I)的化合物,或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,以及任选地,助剂或稀释剂。
在一个另外的方面,本发明提供一种对抗并控制昆虫、螨、线虫或软体动物的方法,该方法包括向有害生物、有害生物的场所、或易受有害生物攻击的植物施用杀昆虫、杀螨、杀线虫、或杀软体动物有效量的如在实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24或25(如上)中任一项或具有式(I-1)、(I-1a)、(I-1b)、(I-2)、(I-2a)和(I-2b)的化合物的实施例(如上)中任一项所定义的具有式(I)的化合物,或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,或如上文所定义的组合物。
在又另外的方面,本发明提供一种用于保护植物繁殖材料免受昆虫、螨、线虫或软体动物攻击的方法,该方法包括用如上文所定义的组合物处理该繁殖材料或该繁殖材料所种植的场所。
根据本发明的用于制备具有式I的化合物的方法通过本领域普通技术人员已知的方法来进行。具有式I-a3的化合物(其中X是SO2,并且A、X1、G1、R1、R2、R7、和R8是如上文在式I下所定义的)可以通过氧化具有式I-a2的化合物(其中X是SO,并且A、X1、G1、R1、R2、R7、和R8是如上文在式I下所定义的)进行制备。该反应可以用例如过酸(如过乙酸或间氯过苯甲酸)、或氢过氧化物(例如像过氧化氢或叔丁基氢过氧化物)、或无机氧化剂(如单过氧二硫酸盐或高锰酸钾)的试剂进行。以类似方式,具有式I-a2的化合物(其中X是SO,并且A、X1、G1、R1、R2、R7、和R8是如上文在式I下所定义的)可以在如上所述的类似条件下通过氧化具有式I-a1的化合物(其中X是S,并且A、X1、G1、R1、R2、R7、和R8是如上文在式I下所定义的)进行制备。这些反应可以在与这些条件相容的各种有机或水性溶剂中,以从低于0℃高至溶剂体系的沸点的温度进行。具有式I-a1的化合物向具有式I-a2和I-a3的化合物的转化在方案1中表示。
方案1
具有式I的化合物(其中Q是如方案2底部所示的基团所定义的,并且其中X、A、X1、G1、R1、R2、R7、和R8是如上文在式I下所定义的)可以通过方案2中所述的方法获得。在氟化锌(II)和钯(0)催化剂(例如三(二苯亚甲基丙酮)二钯(0)-氯仿加合物(Pd2(dba)3)与配体(例如Xantphos)的存在下,在惰性溶剂(例如DMF)中,在100℃-160℃之间的温度下,任选地在微波加热下,将具有式III的化合物(其中Q和A和R1是如上文在式I下所定义的,X是S或SO2,并且Xb1优选是卤素(甚至更优选地是氯、溴或碘))用具有式V的化合物(三甲基甲硅烷基-乙腈)处理,产生具有式II的化合物(其中A、Q、和R1是如上文在通式I下所定义的,并且X是S或SO2)。这样的方法已经例如描述在以下文献中:J.Am.Chem.Soc.2005,127,15824-15832[美国化学会志,2005,127(45),15824-15832]。在碱(例如氢化钠、K2CO3、或Cs2CO3)的存在下,在惰性溶剂(例如THF、DMF、1,4-二噁烷或乙腈)中,可以依次用具有通式VIa和VIb的烷化试剂(其中Xb2优选是Br、I、OSO3Me或OTf,并且R7和R8是在式I下所定义的)处理具有式II的化合物,以给出具有式I的化合物。
可替代地,具有式II的化合物可以经受过量的上述碱和试剂VIb,以获得具有一般类型Ia-4的化合物(其中R7=R8)。可替代地,具有式II的化合物可以通过克拉皮科脱羧(Krapcho decarboxylation))从具有式VII的化合物(其中A、Q、X、和R1是如上文在式I下所定义的,并且R11代表C1-C6烷基基团(优选地是甲基或乙基))获得。这样的方法已经例如描述在以下文献中:Tetradehron Lett.1974,15,1091-1094[四面体通讯,1974,15,1091-1094]。具有式VII的化合物可以通过具有式III的化合物与具有通式VIII的氰基乙酸酯(其中R11代表C1-C6烷基基团(优选地是甲基或乙基))反应来获得。该反应可以在非质子极性溶剂(例如二甲基亚砜(DMSO)、N,N-二甲基甲酰胺(DMF)、或N-甲基吡咯烷酮(NMP))中,在碱(例如K2CO3或Na2CO3)的存在下,在相转移催化剂(“PTC”)存在或不存在下,在20℃-180℃(优选地,80℃-140℃)之间的温度下进行。类似地,过渡金属催化过程是已知的,参见例如Angew.Chem.Int.Ed.2011,50,4470-4474[应用化学国际版本,2011,50,4470-4474]可替代地,可以在催化剂(例如Pd2(dba)3)和配体(例如BINAP)存在或不存在下,使用强碱(例如LiHMDS),在惰性溶剂(例如THF)中,在-20℃和120℃之间的温度下,通过用具有式IV的化合物(其中R7和R8是如上文针对式I所定义的)处理而直接从具有式III的化合物制备具有式I的化合物。这样的方法已经例如描述在以下文献中:Org.Lett.2014,16,6314-6317[有机快报2014,16,6314-6317];J.Org.Chem.2005,70,10186-10189[有机化学杂志2005,70,10186-10189]或Org.Lett.2011,13,1690-1693[有机快报2011,13,1690-1693]。
方案2
可替代地,具有式I的化合物可以如方案3中所描述的制备。通过本领域普通技术人员已知的和描述于例如Tetrahedron 2005,61(46),10827-10852[四面体2005,61(46),10827-10852]中的方法,可以将具有式XII的化合物(其中R1、A、X、R7和R8是如上文针对式I所定义的)处理活化为具有式XI的化合物。例如其中X0是氯的具有式XI的化合物是通过在催化量的DMF的存在下,在惰性溶剂(如二氯甲烷或THF)中,在20℃至100℃之间的温度(优选25℃)下,用例如草酰氯或亚硫酰氯进行处理形成的。任选地在碱(例如三乙胺或吡啶)的存在下,用具有式XI的化合物(其中R2、G1和X1是如在式I中所描述的定义的)处理XI,产生具有式IX的化合物。可替代地,可以通过在惰性溶剂(例如吡啶或四氢呋喃(THF))中,任选地在碱(例如三乙胺)的存在下,在50℃-180℃之间的温度下,用二环己基碳二亚胺(DCC)或1-乙基-3-(3-二甲基氨基丙基)碳二亚胺(EDC)处理具有式XII的化合物,以给出被活化种类XI(其中X0分别是X01和X02)来制备具有式XI的化合物。然后,获得的具有式IX的化合物可通过在酸催化剂(例如甲磺酸、或对甲苯磺酸)的存在下,在惰性溶剂(如N-甲基吡咯烷酮)中,在25℃-180℃之间(优选130℃-170℃)的温度下,进行脱水(例如通过在微波辐射下加热)被转化为具有式I的化合物。这样的方法先前已经描述在WO 2010/125985中。可替代地,在惰性溶剂(如THF)中,在25℃-50℃之间的温度下,可以使用三苯基膦、二异丙基偶氮二羧酸酯将具有式IX的化合物转化为具有式I的化合物(其中X1是O)。先前已经针对这样的转化描述了这样的光延反应(Mitsunobu)条件(参见WO 2009/131237)。具有式X的化合物先前已经描述在WO 2012/086848、WO 2015/000715和WO 2016/116338中。
方案3
具有式XII的化合物(其中R1、A、X、R7和R8是如上文针对式I所定义的)可以通过描述于方案4中的方法来制备。具有式XV的所需起始材料(其中R1、X、A是如上文针对式I所定义的,并且其中Xb1可以是卤素(优选氯、溴或碘)或磺酸酯(像例如三氟甲磺酸酯),最优选地是溴或碘,并且RLG是C1-C4烷基)的合成先前已经描述在例如WO 2016/026848中。在氟化锌(II)和钯(0)催化剂(例如三(二苯亚甲基丙酮)二钯(0)-氯仿加合物(Pd2(dba)3))、配体(例如Xantphos)的存在下,在惰性溶剂(例如DMF)中,在100℃-160℃之间的温度下,任选地在微波加热下,用三甲基甲硅烷基-乙腈(V)处理具有式XV的化合物,产生具有式XIV的化合物(其中X是S或SO2,R1和A是如上文式I中所定义的,并且RLG是C1-C4烷基)。这样的方法已经例如描述在以下文献中:J.Am.Chem.Soc.2005,127,15824-15832[美国化学会志,2005,127(45),15824-15832]。可以在碱(例如氢化钠、K2CO3或Cs2CO3)的存在下,在惰性溶剂(例如THF、DMF、或乙腈)中,依次用具有式VIa或VIb的烷化试剂(其中Xb2优选是Br、I、或OTf,并且R7和R8是在式I下所定义的)处理具有式XIV的化合物,以给出具有式XIII的化合物(其中X是S或SO2,R1、A、R7和R8是如上文式I中所定义的,并且RLG是C1-C4烷基)。可替代地,具有式XIV的化合物可以经受过量的上述碱和试剂VIb,以获得具有一般类型XIII-a的化合物(其中R7=R8)。可替代地,可以在催化剂(例如Pd2(dba)3)和配体(例如BINAP)存在或不存在下,使用强碱(例如LiHMDS),在惰性溶剂(例如THF)中,在-20℃和120℃之间的温度下,通过用具有式IV的化合物(其中R7和R8是如上文针对式I所定义的)处理而直接从具有式XV的化合物制备具有式XIII的化合物。这样的方法已经例如描述在以下文献中:J.Am.Chem.Soc.2005,127,15824-15832[美国化学会志,2005,127,15824-15832];J.Org.Chem.2005,70,10186-10189[有机化学杂志2005,70,10186-10189]或Org.Lett.2014,16,6314-6317[有机快报2014,16,6314-6317]或Org.Lett.2011,13,1690-1693[有机快报2011,13,1690-1693]。
可替代地,具有式XIV的化合物可以通过克拉皮科脱羧从具有式XVI的化合物(其中A、X、和R1是如上文在式I下所定义的,RLG和R11彼此独立地代表C1-C6烷基基团(优选甲基或乙基))获得。这样的方法已经例如描述在以下文献中:Tetradehron Lett.1974,15,1091-1094[四面体通讯,1974,15,1091-1094]。具有式XVI的化合物可以通过具有式XV的化合物与具有式VIII的氰基乙酸酯(其中R11代表C1-C6烷基基团(优选地是甲基或乙基))反应来获得。该反应可以在非质子极性溶剂(例如二甲基亚砜(DMSO)、N,N-二甲基甲酰胺(DMF)、或N-甲基吡咯烷酮(NMP))中,在碱(例如K2CO3或Na2CO3)的存在下,在相转移催化剂(“PTC”)存在或不存在下,在20℃-180℃(优选地,80℃-140℃)之间的温度下进行。类似地,过渡金属催化过程是已知的,参见例如Angew.Chem.Int.Ed.2011,50,4470-4474[应用化学国际版本,2011,50,4470-4474]可以在本领域技术人员已知的条件下通过皂化将具有式XIII或XIII-a的化合物转化为具有式XII的化合物。具有式IV、V、VIa、VIb、和VIII的化合物是可商购的,或制备这些化合物的方法是本领域技术人员已知的。具有式XV的化合物是已知的,并且这些化合物的合成已经报告在文献中,例如参见WO 2016/005263。
可以在本领域技术人员已知的条件下通过皂化将具有式XIII或XIII-a的化合物转化为具有式XII的化合物。具有式IV、V和VIa、VIb和VIII的化合物是可商购的,或制备这些化合物的方法是本领域技术人员已知的。
方案4
具有式IX、XI、XII、XIII、XVI的化合物是新颖的,是为了制备具有式I的化合物而特别研发的。
因此,在本发明的又另外的方面,提供了:
具有式IX的化合物,
其中
A是CH或N,优选N;
X是S、SO或SO2,优选地是S或SO2;
R1是C1-C4烷基,优选乙基;
G1是N或CH;
R3是氢或C1-C4烷基,优选地是甲基;
R2是卤素、C1-C6卤代烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基或C1-C6卤代烷氧基;优选地是CF3;
R7是氢、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基,优选地,R7是甲基或氟;以及
R8是卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基,优选地,R8是甲基或氟;或其位置异构体,或其异构混合物;
以及
具有式XI的化合物,
其中
A是CH或N,优选N;
X是S、SO或SO2,优选地是S或SO2;
R1是C1-C4烷基,优选乙基;
R7是氢、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基,优选地,R7是甲基或氟;以及
R8是卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基,优选地,R8是甲基或氟;
以及
具有式XII的化合物,
其中
A是CH或N,优选N;
X是S、SO或SO2,优选地是S或SO2;
R1是C1-C4烷基,优选乙基;
R7是氢、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基,优选地,R7是甲基或氟;
R8是卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基,优选地,R8是甲基或氟;
以及
具有式XIII的化合物,
其中
A是CH或N,优选N;
X是S、SO或SO2,优选地是S或SO2;
R1是C1-C4烷基,优选乙基;
R7是氢、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基,优选地,R7是甲基或氟;
R8是卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基,优选地,R8是甲基或氟;以及
RLG是C1-C4烷基,优选地是甲基或乙基;
以及
具有式XVI的化合物,
其中
A是CH或N,优选N;
X是S、SO或SO2,优选地是S或SO2;
R1是C1-C4烷基,优选乙基;
R11是C1-C4烷基,优选地是甲基或乙基;以及
RLG是C1-C4烷基,优选地是甲基或乙基。
当制备具有式(IX)的化合物时,有时获得副产物位置异构体(即具有式(IX-z)的化合物:
其中A、X、R1、G1、R3、R2、R7和R8是如上文针对具有式(IX)的化合物所定义的。
这些反应物可以在碱的存在下进行反应。适合的碱的实例是碱金属或碱土金属氢氧化物、碱金属或碱土金属氢化物、碱金属或碱土金属酰胺、碱金属或碱土金属醇盐、碱金属或碱土金属乙酸盐、碱金属或碱土金属碳酸盐、碱金属或碱土金属二烷基酰胺或碱金属或碱土金属烷基甲硅烷基酰胺、烷基胺、亚烷基二胺、游离的或N-烷基化的饱和或不饱和的环烷基胺、碱性杂环、氢氧化铵以及碳环胺。可以提及的实例是氢氧化钠、氢化钠、氨基钠、甲醇钠、乙酸钠、碳酸钠、叔丁醇钾、氢氧化钾、碳酸钾、氢化钾、二异丙氨基锂、双(三甲基硅烷基)酰胺钾、氢化钙、三乙胺、二异丙基乙胺、三亚乙基二胺、环己胺、N-环己基-N,N-二甲胺、N,N-二乙苯胺、吡啶、4-(N,N-二甲氨基)吡啶、奎宁环、N-甲基吗啉、苄基三甲基铵氢氧化物以及1,8-二氮杂二环[5.4.0]十一-7-烯(DBU)。
这些反应物可以按照原样彼此进行反应,即:不用添加溶剂或稀释剂。然而,在大多数情况下,添加惰性溶剂或稀释剂或这些的混合物是有利的。如果该反应在碱的存在下进行,那么这些过量使用的碱(如三乙胺、吡啶、N-甲基吗啉或N,N-二乙苯胺)还可以充当溶剂或稀释剂。
该反应有利地是在从约-80℃到约+140℃,优选从约-30℃到约+100℃,在许多情况下在介于环境温度与约+80℃之间的温度下进行。
具有式I的化合物能以本身已知的方法转化为另一种具有式I的化合物,这是通过以常规方式将具有式I的起始化合物的一个或多个取代基用根据本发明的另一个或其他或多个取代基的替代来实现的。
取决于所选的适合各自情况的反应条件以及起始材料,有可能例如,在一个反应步骤中仅将一个取代基用根据本发明的另一个取代基替代,或者在同一个反应步骤中可以将多个取代基用多个根据本发明的其他取代基来替代。
具有式I的这些化合物的盐能以本身已知的方式进行制备。因此,例如,具有式I的化合物的酸加成盐是通过用适合的酸或合适的离子交换试剂进行处理来获得的,并且与碱的盐是通过用适合的碱或用合适的离子交换试剂进行处理来获得的。
具有式I的化合物的盐能以常规方式转化为游离的化合物I、酸加成盐(例如通过用合适的碱性化合物或用合适的离子交换试剂进行处理)以及碱盐(例如通过用合适的酸或用合适的离子交换试剂进行处理)。
具有式I的化合物的盐能以本身已知的方式转化为具有式I的化合物的其他盐、酸加成盐,例如转变成为其他酸加成盐,例如通过在合适的溶剂中用酸的合适的金属盐(如钠盐、钡盐或银盐,例如用乙酸银)来处理无机酸的盐(如盐酸盐),在该溶剂中,所形成的无机盐(例如氯化银)是不溶的并且因此从反应混合物中沉淀出。
取决于程序或反应条件,具有成盐特性的这些具有式I的化合物能以游离形式或盐的形式获得。
根据分子中存在的不对称碳原子的数目、绝对和相对构型和/或根据分子中存在的非芳香族双键的构型,在每种情况下为游离形式或为盐形式的具有式I的化合物和适当时其互变异构体可以可能的异构体之一的形式或作为其混合物存在,例如以纯异构体的形式,如对映体和/或非对映体,或作为异构体混合物,如对映异构体混合物,例如外消旋体、非对映体混合物或外消旋体混合物存在;本发明涉及纯异构体以及所有可能的异构体混合物,并且在上文和下文中都应如此理解,即使立体化学细节未在所有情况下明确提及。
处于游离形式或处于盐形式的具有式I的化合物的非对映异构体混合物或外消旋体混合物(它们的获得可以取决于已选定的起始材料和程序)能够在这些组分的物理化学差异的基础上,例如通过分步结晶、蒸馏和/或层析法以已知的方式分离成纯的非对映异构体或外消旋体。
能够以一种类似方式获得的对映异构体混合物(例如外消旋体)可以通过已知方法拆分成光学对映体,例如通过从一种光学活性溶剂再结晶;通过在手性吸附剂上的层析法,例如在乙酰纤维素上的高效液相层析法(HPLC);借助于合适的微生物,通过用特异性固定化酶裂解;通过形成包含化合物,例如使用手性冠醚,其中仅一个对映异构体被络合;或通过转化成非对映异构盐,例如通过使一种碱性最终产物外消旋体与一种光学活性酸(例如羧酸,例如樟脑酸、酒石酸或苹果酸或磺酸,例如樟脑磺酸)反应,并且分离能够以此方式获得的非对映异构体混合物,例如基于其不同溶解度通过分步结晶,从而获得非对映异构体,从这些非对映异构体可以通过合适的试剂(例如碱性试剂)的作用使所希望的对映异构体变成游离。
纯的非对映异构体或对映异构体能根据本发明来获得,不仅是通过分离合适的异构体混合物,还可以是通过普遍已知的非对映立体选择性或对映选择性合成的方法,例如通过根据本发明利用一种合适的立体化学的起始材料进行该方法。
可以通过使具有式I的化合物与适合的氧化剂(例如H2O2/尿素加合物)在酸酐(例如三氟乙酸酐)的存在下进行反应来制备N-氧化物。这样的氧化例如从以下文献中已知:J.Med.Chem.,32(12),2561-73,1989[药物化学杂志,32(12),2561-73,1989]或WO 00/15615。
有利的是在每一情况中分离或合成生物学地更有效的异构体,例如对映异构体或非对映异构体或异构体混合物,例如对映异构体混合物或非对映异构体混合物,如果个别组分具有不同的生物活性。
具有式I的化合物和适当时其互变异构体(在每种情况下处于游离形式或处于盐形式)如果适当的话还能以水合物的形式获得和/或包括其他溶剂,例如可以用于使以固体形式存在的化合物结晶的那些。
下表X的化合物可以根据以上所描述的方法制备。随后的这些实例旨在说明本发明并且展示具有式I的优选化合物。
表X:该表披露了具有式I的15个取代基定义X.001至X.015:
其中R2、G1、X1、A、R1、R7和R8是如下定义的:
表X:
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以及表X的化合物的N-氧化物。Me代表甲基基团;Et是乙基基团;i-Pr是异丙基基团;C(O)OEt是乙氧基羰基基团;MeO是甲氧基基团;并且MeOCH2是甲氧基甲基基团。
表1:该表披露了具有式I-1的23种化合物1.001至1.023,其中X是S,并且R2、G1、X1、A、R1、R7和R8是如在表X中所定义的。例如,化合物1.001具有以下结构:
表2:该表披露了具有式I-1a的23种化合物2.001至2.023,其中X是SO,并且R2、G1、X1、A、R1、R7和R8是如表X中所定义的。
表3:该表披露了具有式I-1a的23种化合物3.001至3.023,其中X是SO2,并且R2、G1、X1、A、R1、R7和R8是如在表X中所定义的。
根据本发明的具有式I的化合物在有害生物控制领域中是有预防和/或治疗价值的活性成分,即使是在低的施用量下,它们具有非常有利的杀生物谱并且是温血物种、鱼以及植物良好耐受的。根据本发明的这些活性成分作用于正常敏感的以及还有抗药的动物有害生物(如昆虫或蜱螨目的代表)的所有的或个别的发育阶段。根据本发明的活性成分的杀昆虫或杀螨活性可以本身直接显示,亦即或者立即或者仅在过去一些时间之后(例如在蜕皮期间)发生破坏有害生物;或间接显示,例如降低产卵和/或孵化率。
上述动物有害生物的实例是:
来自蜱螨目,例如
下毛瘿螨属(Acalitus spp.)、针刺瘿螨属(Aculus spp)、窄瘿螨属(Acaricalusspp.)、瘤瘿螨属(Aceria spp.)、粗脚粉螨(Acarus siro)、钝眼蜱属(Amblyomma spp.)、锐缘蜱属(Argas spp.)、牛蜱属(Boophilus spp.)、短须螨属(Brevipalpus spp.)、苔螨属(Bryobia spp)、上三节瘿螨属(Calipitrimerus spp.)、皮螨属(Chorioptes spp.)、鸡皮刺螨(Dermanyssus gallinae)、表皮螨属(Dermatophagoides spp)、始叶螨属(Eotetranychus spp)、瘿螨属(Eriophyes spp.)、半跗线螨属(Hemitarsonemus spp)、璃眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、小爪螨属(Olygonychus spp)、钝缘蜱属(Ornithodoros spp.)、侧多食跗线螨(Polyphagotarsone latus)、全爪螨属(Panonychusspp.)、桔芸锈螨(Phyllocoptruta oleivora)、植食螨(Phytonemus spp.)、跗线螨属(Polyphagotarsonemus spp)、痒螨属(Psoroptes spp.)、扇头蜱属(Rhipicephalusspp.)、根嗜螨属(Rhizoglyphus spp.)、疥螨属(Sarcoptes spp.)、狭跗线螨属(Steneotarsonemus spp)、跗线属(Tarsonemus spp.)以及叶螨属(Tetranychus spp.);
来自虱目,例如
血虱属(Haematopinus spp.)、长颚虱属(Linognathus spp.)、人虱(Pediculusspp.)、天疱疮属(Pemphigus spp.)以及木虱(Phylloxera spp.);
来自鞘翅目,例如
缺隆叩甲属(Agriotes spp.)、欧洲鳃角金龟(Amphimallon majale)、东方异丽金龟(Anomala orientalis)、花象属(Anthonomus spp.)、蜉金龟属(Aphodius spp)、玉米拟花萤(Astylus atromaculatus)、Ataenius属、甜菜隐食甲(Atomaria linearis)、甜菜胫跳甲(Chaetocnema tibialis)、萤叶甲属(Cerotoma spp)、单叶叩甲属(Conoderus spp)、根颈象属(Cosmopolites spp.)、绿金龟(Cotinisnitida)、象虫属(Curculio spp.)、圆头犀金龟属(Cyclocephala spp)、圆头犀金龟属(Dermestes spp.)、根萤叶甲属(Diabroticaspp.)、阿根廷兜虫(Diloboderus abderus)、食植瓢虫属(Epilachna spp.)、Eremnus属、黑异爪蔗金龟(Heteronychus arator)、咖啡果小蠹(Hypothenemus hampei)、Lagriavilosa、马铃薯甲虫(Leptinotarsa decemLineata)、稻水象属(Lissorhoptrus spp.)、Liogenys属、Maecolaspis属、栗色绒金龟(Maladera castanea)、美洲叶甲亚种(Megascelis spp)、油菜花露尾甲(Melighetes aeneus)、金龟属(Melolontha spp.)、Myochrous armatus、锯谷盗属(Orycaephilus spp.)、耳喙象属(Otiorhynchus spp.)、鳃角金龟属(Phyllophaga spp.)、斑象属(Phlyctinus spp.)、丽金龟属(Popillia spp.)、油菜跳甲属(Psylliodes spp.)、Rhyssomatus aubtilis、劫根蠹属(Rhizopertha spp.)、金龟子科(Scarabeidae)、米象属(Sitophilus spp.)、麦蛾属(Sitotroga spp.)、伪切根虫属(Somaticus spp.)、Sphenophorus属、大豆茎象(Sternechus subsignatus)、拟步行虫属(Tenebrio spp.)、拟谷盗属(Tribolium spp.)以及斑皮蠹属(Trogoderma spp.);
来自双翅目,例如
伊蚊属(Aedes spp.)、疟蚊属(Anopheles spp)、高梁芒蝇(Antherigonasoccata.)、橄榄果实蝇(Bactrocea oleae)、花园毛蚊(Bibio hortulanus)、迟眼蕈蚊属(Bradysia spp.)、红头丽蝇(Calliphora erythrocephala)、小条实蝇属(Ceratitisspp.)、金蝇属(Chrysomyia spp.)、库蚊属(Culex spp.)、黄蝇属(Cuterebra spp.)、寡鬃实蝇属(Dacus spp.)、地种蝇属(Delia spp)、黑腹果蝇(Drosophilamelanogaster)、厕蝇属(Fannia spp.)、胃蝇属(Gastrophilus spp.)、Geomyza tripunctata、舌蝇属(Glossinaspp.)、皮蝇属(Hypoderma spp.)、虱蝇属(Hyppobosca spp.)、斑潜蝇属(Liriomyzaspp.)、绿蝇属(Lucilia spp.)、潜蝇属(Melanagromyza spp.)、家蝇属(Musca spp.)、狂蝇属(Oestrus spp.)、瘿蚊属(Orseolia spp.)、瑞典麦秆蝇(Oscinella frit)、藜泉蝇(Pegomyia hyoscyami)、草种蝇属(Phorbia spp.)、绕实蝇属(Rhagoletis spp)、Riveliaquadrifasciata、Scatella属、蕈蚊属(Sciara spp.)、刺蝇属(Stomoxys spp.)、虻属(Tabanus spp.)、绦虫属(Tannia spp.)以及大蚊属(Tipula spp.);
来自半翅目(Hemiptera),例如
瘤缘蝽(Acanthocoris scabrator)、绿蝽属、苜蓿盲蝽、Amblypeltanitida、海虾盾缘蝽(Bathycoelia thalassina)、土长蝽属、臭虫属、Clavigralla tomentosicollis、盲蝽属(Creontiades spp.)、可可瘤盲蝽、Dichelops furcatus、棉红蝽属、Edessa属、美洲蝽属(Euchistus spp.)、六斑菜蝽(Eurydema pulchrum)、扁盾蝽属、茶翅蝽、具凹巨股长蝽(Horciasnobilellus)、稻缘蝽属、草盲蝽属、热带硕蚧属、卷心菜斑色蝽(Murgantiahistrionic)、Neomegalotomus属、烟盲蝽(Nesidiocoris tenuis)、绿蝽属、拟长蝽(Nysiussimulans)、Oebalus insularis、皮蝽属、壁蝽属、红猎蝽属、可可盲蝽象、Scaptocoriscastanea、黑蝽属(Scotinophara spp.)、Thyanta属、锥鼻虫属、木薯网蝽(Vatigailludens);
无网长管蚜属、Adalges spp.、Agalliana ensigera、Agonoscena targionii、粉虱属(Aleurodicus spp.)、Aleurocanthus spp.、甘蔗穴粉虱、软毛粉虱(Aleurothrixusfloccosus)、甘蓝粉虱(Aleyrodes brassicae)、棉叶蝉(Amarasca biguttula)、Amritodusatkinson、肾圆盾蚧属、蚜科、蚜属、蚧属(Aspidiotus spp.)、茄沟无网蚜、Bactericeracockerelli、小粉虱属、Brachycaudus spp.、甘蓝蚜、喀木虱属、双尾蚜(Cavariellaaegopodii Scop.)、蜡蚧属、褐圆蚧、网籽草叶圆蚧、Cicadella spp.、大白叶蝉(Cofanaspectra)、隐瘤蚜属、Cicadulina spp.、褐软蚧、玉米黄翅叶蝉、裸粉虱属、柑橘木虱、麦双尾蚜、西圆尾蚜属、小绿叶蝉属、苹果绵蚜、葡萄斑叶蝉属、蜡蛤属、赤桉木虱(Glycaspisbrimblecombei)、菜缢管蚜、Hyalopterus spp.、超瘤蚜种、檬果绿叶蝉(Idioscopusclypealis)、Jacobiasca lybica、灰飞虱属、球坚蚧、蛎盾蚧属、萝卜蚜(Lopaphiserysimi)、Lyogenys maidis、长管蚜属、Mahanarva spp.、蛾蜡蝉科(Metcalfa pruinosa)、麦无网蚜、Myndus crudus、瘤蚜属、台湾韭蚜、黑尾叶蝉属、褐飞虱属(Nilaparvata spp.)、梨大绿蚜、Odonaspis ruthae、寄生甘蔗绵蚜、杨梅缘粉虱、考氏木虱、片盾蚧属、瘿绵蚜属、玉米蜡蝉、扁角飞虱属、忽布疣蚜、根瘤蚜属、动性球菌属、白盾蚧属、粉蚧属、棉盲蝽(Pseudatomoscelis seriatus)、木虱属、棉蚧(Pulvinaria aethiopica)、笠圆盾蚧属、Quesada gigas、电光叶蝉(Recilia dorsalis)、缢管蚜属、黑盔蚧属、带叶蝉属、二叉蚜属、麦蚜属(Sitobion spp.)、白背飞虱、Spissistilus festinus、条斑飞虱(TarophagusProserpina)、声蚜属、粉虱属、Tridiscus sporoboli、葵粉蚧属(Trionymus spp.)、非洲木虱、桔矢尖蚧、Zygina flammigera、Zyginidia scutellaris;
来自膜翅目,例如
顶切叶蚁属(Acromyrmex)、三节叶蜂属(Arge spp.)、布切叶白蚁属(Atta spp.)、茎叶蜂属(Cephus spp.)、松叶蜂属(Diprion spp.)、锯角叶蜂科(Diprionidae)、松叶蜂(Gilpinia polytoma)、梨实蜂属(Hoplocampa spp.)、毛蚁属(Lasius spp.)、小黄家蚁(Monomorium pharaonis)、新松叶蜂属(Neodiprion spp.)、农蚁属(Pogonomyrmex spp)、Slenopsis invicta、水蚁属(Solenopsis spp.)以及胡蜂属(Vespa spp.);
来自等翅目,例如
家白蚁属、白蚁(Corniternes cumulans)、楹白蚁属、大白蚁属、澳白蚁属、小白蚁属、散白蚁属;热带火蚁
来自鳞翅目,例如
长翅卷蛾属、褐带卷蛾属、透翅蛾属、地夜蛾属、棉叶虫、Amylois spp.、黎豆夜蛾、黄卷蛾属、银蛾属(Argyresthia spp.)、带卷蛾属、丫纹夜蛾属、棉潜蛾、玉米楷夜蛾、粉斑螟蛾、桃蛀果蛾、禾草螟属、卷叶蛾属、越蔓桔草螟(Chrysoteuchia topiaria)、葡萄果蠹蛾、卷叶螟属、云卷蛾属、纹卷蛾属、鞘蛾属、磷翅目粉蝶、Cosmophila flava、草螟属、大菜螟、苹果异形小卷蛾、黄杨木蛾、小卷蛾属、黄杨绢野螟、杆草螟属、苏丹棉铃虫、金刚钻属、非洲茎螟、粉螟属、叶小卷蛾属(Epinotia spp)、细斑灯蛾、Etiella zinckinella、花小卷蛾属、环针单纹蛾、黄毒蛾属、切根虫属、Feltia jaculiferia、Grapholita spp.、绿青虫蛾、实夜蛾属、菜螟、切叶野螟属(Herpetogramma spp)、美国白蛾、番茄蠹蛾、Lasmopalpuslignosellus、旋纹潜叶蛾、潜叶细蛾属、葡萄花翅小卷蛾、Loxostege bifidalis、毒蛾属、潜蛾属、幕枯叶蛾属、甘蓝夜蛾、烟草天蛾、Mythimna spp、夜蛾属、秋尺蛾属、Orniodesindica、欧洲玉米螟、超小卷蛾属、褐卷蛾属、小眼夜蛾、蛀茎夜蛾、Pectinophora gossypi-ela、咖啡潜叶蛾、一星黏虫、马铃薯麦蛾、菜粉蝶、粉蝶属、小菜蛾、芽蛾属、尺叶蛾属、薄荷灰夜蛾、西方豆地香(Richia albicosta)、白禾螟属(Scirpophaga spp.)、蛀茎夜蛾属、长须卷蛾属、灰翅夜蛾属、棉大卷叶螟、兴透翅蛾属、异舟蛾属、卷叶蛾属、粉纹夜蛾、番茄斑潜蝇、以及巢蛾属;
来自食毛目,例如
畜虱属(Damalinea spp.)和啮毛虱属(Trichodectes spp.);
来自直翅目,例如
蠊属、小蠊属、蝼蛄属、马德拉蜚蠊、飞蝗属、北痣蟋蟀(Neocurtillahexadactyla)、大蠊属、痣蟋蟀属(Scapteriscus spp.)、以及沙漠蝗属;
来自啮虫目,例如
虱啮属(Liposcelis spp.);
来自蚤目,例如
角叶蚤属(Ceratophyllus spp.)、栉头蚤属(Ctenocephalides spp.)以及开皇客蚤(Xenopsylla cheopis);
来自缨翅目,例如
Calliothrips phaseoli、花蓟马属、阳蓟马属、褐带蓟马属、单亲蓟马属(Parthenothrips spp.)、非洲桔硬蓟马(Scirtothrips aurantii)、大豆蓟马(Sericothrips variabilis)、带蓟马属、蓟马属;
来自缨尾目,例如衣鱼(Lepisma saccharina)。
根据本发明的活性成分可用于控制、也就是遏制或破坏上述类型的有害生物,这些有害生物特别出现在植物上,尤其是在农业中、在园艺中以及在林业中的有用的植物和观赏植物上,或者在这些植物的器官上,例如果实、花、叶、茎、块茎或根,并且在一些情况下,甚至在一个随后的时间点形成的植物器官仍保持受保护抵抗这些有害生物。
适宜的目标作物具体是,谷物,如小麦、大麦、黑麦、燕麦、稻、玉米或高梁;甜菜,如糖用甜菜或饲料甜菜;水果,例如梨果、核果或无核小果,如苹果、梨、李子、桃、杏、樱桃或浆果,例如草莓、覆盆子或黑莓;豆科作物,如菜豆、小扁豆、豌豆或大豆;油料作物,如油菜、芥菜、罂粟、橄榄、向日葵、椰子、蓖麻、可可豆或落花生;瓜类作物,如南瓜、黄瓜或甜瓜;纤维植物,如棉花、亚麻、大麻或黄麻;柑橘类水果,如橙子、柠檬、葡萄柚或橘子;蔬菜,如菠菜、莴苣、芦笋、卷心菜、胡萝卜、洋葱、番茄、马铃薯或灯笼椒;樟科,如鳄梨、肉桂或樟脑;以及还有烟草、坚果、咖啡、茄子、甘蔗、荼、胡椒、葡萄藤、蛇麻草、车前草科以及乳胶植物。
本发明的组合物和/或方法还可以用在任何观赏植物和/或蔬菜作物(包括花、灌木、阔叶树和常绿植物)上。
例如,本发明可以用在任何以下观赏植物物种上:藿香蓟属、假面花属(Alonsoaspp.)、银莲花属、南非葵、春黄菊属、金鱼草属、紫菀属、秋海棠属(例如丽格海棠、四季秋海棠、球根秋海棠(B.tubéreux))、叶子花属、雁河菊属(Brachycome spp.)、芸苔属(观赏植物)、蒲包草属、辣椒、长春花、美人蕉属、矢车菊属、菊属、瓜叶菊属(银叶菊)、金鸡菊属、青锁龙(Crassula coccinea)、火红萼距花(Cuphea ignea)、大丽花属、翠雀属、荷包牡丹、彩虹菊属(Dorotheantus spp.)、洋桔梗、连翘属、倒挂金钟属、鼠曲草老颧草(Geraniumgnaphalium)、大丁草属、千日红、天芥菜属、向日葵属、木槿属、绣球花属、绣球属、嫣红蔓、凤仙花属(非洲凤仙花)、血苋属(Iresines spp.)、伽蓝菜属、马缨丹、三月花葵、狮耳花、百合属、日中花属、沟酸浆属、美国薄荷属、龙面花属、万寿菊属、石竹属(康乃馨)、美人蕉属、酢浆草属、雏菊属、天竺葵属(盾叶天竺葵、马蹄纹天竺葵)、堇菜属(三色堇)、碧冬茄属、草夹竹桃属、香茶菜属(Plecthranthus spp.)、一品红属、爬山虎属(五叶爬山虎、爬山虎)、报春花属、毛茛属、杜鹃花属、蔷薇属(玫瑰)、黄雏菊属、非洲堇属、鼠尾草属、紫扇花(Scaevola aemola)、蛾蝶花(Schizanthus wisetonensis)、景天属、茄属、苏非尼亚矮牵牛属(Surfinia spp.)、万寿菊属、烟草属、马鞭草属、百日草属以及其他花坛植物。
例如,本发明可以用于任何以下蔬菜物种:葱属(大蒜、洋葱、火葱(A.oschaninii)、韭葱、小葱、大葱)、有喙欧芹、旱芹、芦笋、甜菜、芸苔属(甘蓝、大白菜、芜菁)、辣椒、鹰嘴豆、苦苣、菊苣属(菊苣、苦苣)、西瓜、黄瓜属(黄瓜、甜瓜)、南瓜属(西葫芦、印度南瓜)、菜蓟属(朝鲜蓟、刺苞菜蓟)、胡萝卜、茴香、金丝桃属、莴苣、番茄属(番茄、樱桃番茄)、薄荷属、罗勒、香芹、菜豆属(菜豆、荷包豆)、豌豆、萝卜、食用大黄、迷迭香属、鼠尾草属、黑婆罗门参、茄子、菠菜、新缬草属(莴苣缬草、V.eriocarpa)以及蚕豆。
优选的观赏植物物种包括非洲堇、秋海棠属、大丽花属、大丁草属、绣球属、马鞭草属、蔷薇属、伽蓝菜属、一品红属、紫菀属、矢车菊属、金鸡菊属、翠雀属、美国薄荷属、草夹竹桃属、黄雏菊属、景天属、碧冬茄属、堇菜属、凤仙花属、老鹳草属、菊属、毛茛属、倒挂金钟属、鼠尾草属、绣球花属、迷迭香、鼠尾草、圣约翰草、薄荷、甜椒、番茄和黄瓜。
根据本发明所述的活性成分尤其适合于控制棉花、蔬菜、玉米、水稻以及大豆作物上的扁豆蚜、黄瓜条叶甲、烟芽夜蛾、桃蚜、小菜蛾以及海灰翅夜蛾。根据本发明的这些活性成分另外尤其适合于控制甘蓝夜蛾(优选地在蔬菜上)、苹果蠹蛾(优选地在苹果上)、小绿叶蝉(优选地在蔬菜、葡萄园里)、马铃薯叶甲(优选地在马铃薯上)以及二化螟(优选地在水稻上)。
根据本发明所述的活性成分尤其适合于控制棉花、蔬菜、玉米、水稻以及大豆作物上的扁豆蚜、黄瓜条叶甲、烟芽夜蛾、桃蚜、小菜蛾以及海灰翅夜蛾。根据本发明的这些活性成分另外尤其适合于控制甘蓝夜蛾(优选地在蔬菜上)、苹果蠹蛾(优选地在苹果上)、小绿叶蝉(优选地在蔬菜、葡萄园里)、马铃薯叶甲(优选地在马铃薯上)以及二化螟(优选地在水稻上)。在另一个方面,本发明还可以涉及控制由植物寄生的线虫(内寄生的-、半内寄生的-以及外寄生的线虫)对植物或其部分引起损害的方法,尤其是以下植物寄生的线虫,如根结线虫(root knot nematodes)、北方根结线虫(Meloidogyne hapla)、南方根结线虫(Meloidogyne incognita)、爪哇根结线虫(Meloidogyne javanica)、花生根结线虫(Meloidogyne arenaria)以及其他根结线虫属种类(Meloidogyne species);孢囊形成线虫(cyst-forming nematodes)、马铃薯金线虫(Globodera rostochiensis)以及其他球孢囊线虫属种类(Globodera species);禾谷孢囊线虫(Heterodera avenae)、大豆胞囊线虫(Heterodera glycines)、甜菜胞囊线虫(Heterodera schachtii)、红三叶异皮线虫(Heterodera trifolii)、以及其他异皮线虫属种类(Heterodera species);种瘿线虫(Seed gall nematodes)、粒线虫属种类(Anguina species);茎及叶面线虫(Stem andfoliar nematodes)、滑刃线虫属种类(Aphelenchoides species);刺毛线虫(Stingnematodes)、长尾刺线虫(Belonolaimus longicaudatus)以及其他刺线虫属种类;松树线虫(Pine nematodes)、松材线虫(Bursaphelenchus xylophilus)以及其他伞滑刃属种类(Bursaphelenchus species);环形线虫(Ring nematodes)、环线虫属种类(Criconemaspecies)、小环线虫属种类(Criconemella species)、轮线虫属种类(Criconemoidesspecies)、中环线虫属种类(Mesocriconema species);茎及鳞球茎线虫(Stem and bulbnematodes)、腐烂茎线虫(Ditylenchus destructor)、鳞球茎茎线虫(Ditylenchusdipsaci)以及其他茎线虫属种类(Ditylenchus species);锥线虫(Awl nematodes)、锥线虫属种类(Dolichodorus species);螺旋线虫(Spiral nematodes)、多头螺旋线虫(Heliocotylenchus multicinctus)以及其他螺旋线虫属种类(Helicotylenchusspecies);鞘及鞘形线虫(Sheath and sheathoid nematodes)、鞘线虫属种类(Hemicycliophora species)以及半轮线虫属种类(Hemicriconemoides species);潜根线虫属种类(Hirshmanniella species);支线虫(Lance nematodes)、冠线虫属种类(Hoploaimus species);假根结线虫(false rootknot nematodes)、珍珠线虫属种类(Nacobbus species);针状线虫(Needle nematodes)、横带长针线虫(Longidoruselongatus)以及其他长针线虫属种类(Longidorus species);大头针线虫(Pinnematodes)、短体线虫属种类(Pratylenchus species);腐线虫(Lesion nematodes)、花斑短体线虫(Pratylenchus neglectus)、穿刺短体线虫(Pratylenchus penetrans)、弯曲短体线虫(Pratylenchus curvitatus)、古氏短体线虫(Pratylenchus goodeyi)以及其他短体线虫属种类(Pratylenchus species);柑桔穿孔线虫(Burrowing nematodes)、香蕉穿孔线虫(Radopholus similis)以及其他内侵线虫属种类(Radopholus species);肾形线虫(Reniform nematodes)、罗柏氏盘旋线虫(Rotylenchus robustus)、肾形盘旋线虫(Rotylenchus reniformis)以及其他盘旋线虫属种类(Rotylenchus species);盾线虫属种类(Scutellonema species);短粗根线虫(Stubby root nematodes)、原始毛刺线虫(Trichodorus primitivus)以及其他毛刺线虫属种类(Trichodorus species)、拟毛刺线虫属种类(Paratrichodorus species);矮化线虫(Stunt nematodes)、马齿苋矮化线虫(Tylenchorhynchus claytoni)、顺逆矮化线虫(Tylenchorhynchus dubius)以及其他矮化线虫属种类(Tylenchorhynchus species);柑桔线虫(Citrus nematodes)、穿刺线虫属种类(Tylenchulus species);短剑线虫(Dagger nematodes)、剑线虫属种类(Xiphinemaspecies);以及其他植物寄生的线虫种类,如亚粒线虫属(Subanguina spp.)、Hypsoperine属、大刺环线虫属(Macroposthonia spp.)、Melinius属、刻点胞囊属(Punctodera spp.)、以及五沟线虫属(Quinisulcius spp.)。
本发明所述的化合物还具有针对软体动物的活性。这些软体动物的实例包括例如苹果螺科;阿勇蛞蝓属(Arion)(灰黑阿勇蛞蝓(A.ater)、环斑阿勇蛞蝓(A.circumscriptus)、庭院阿勇蛞蝓(A.hortensis)、红棕阿勇蛞蝓(A.rufus));巴蜗牛科(灌木巴蜗牛(Bradybaena fruticum));蜗牛属(庭院蜗牛(C.hortensis)、森林蜗牛(C.Nemoralis));ochlodina;灰蛞蝓属(Deroceras)(野灰蛞蝓(D.agrestis)、D.empiricorum、田灰蛞蝓(D.laeve)、庭园灰蛞蝓(D.reticulatum));圆盘螺属(Discus)(D.rotundatus);Euomphalia;土蜗属(Galba)(截形土蜗(G.trunculata));小蜗牛属(Helicelia)(伊塔拉小蜗牛(H.itala)、布维小蜗牛(H.obvia));大蜗牛科Helicigonaarbustorum);Helicodiscus;大蜗牛属(Helix)(开放大蜗牛(H.aperta));蛞蝓属(Limax)(灰黑蛞蝓(L.cinereoniger)、黄蛞蝓(L.flavus)、边缘蛞蝓(L.marginatus)、大蛞蝓(L.maximus)、柔蛞蝓(L.tenellus));椎实螺属(Lymnaea);Milax(M.gagates、M.marginatus、M.sowerbyi);钻螺属(Opeas);瓶螺属(Pomacea)(P.canaticulata);瓦娄蜗牛属(Vallonia)和Zanitoides。
术语“作物”应理解为还包括已经通过使用重组DNA技术而被这样转化使其能够合成一种或多种选择性作用毒素的作物植物,这些毒素如已知,例如来自产毒素的细菌,尤其是芽孢杆菌属的那些。
可以通过此类转基因植物表达的毒素包括例如杀昆虫蛋白,例如来自于蜡样芽孢杆菌或日本甲虫芽孢杆菌的杀昆虫蛋白;或来自于苏云金芽孢杆菌的杀昆虫蛋白,如δ-内毒素,例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C,或营养期杀虫蛋白(Vip),例如Vip1、Vip2、Vip3或Vip3A;或线虫寄生性细菌的杀虫蛋白,例如光杆状菌属或致病杆菌属,如发光光杆状菌、嗜线虫致病杆菌;由动物产生的毒素,如蝎毒素、蜘蛛毒素、黄蜂毒素和其他昆虫特异性神经毒素;由真菌产生的毒素,如链霉菌毒素;植物凝集素,如豌豆凝集素、大麦凝集素或雪花莲凝集素;凝集素类;蛋白酶抑制剂,如胰蛋白酶抑制剂、丝氨酸蛋白酶抑制剂、马铃薯贮存蛋白(patatin)、半胱氨酸蛋白酶抑制剂、木瓜蛋白酶抑制剂;核糖体失活蛋白(RIP),如蓖麻蛋白、玉米-RIP、相思豆毒蛋白、丝瓜籽毒蛋白、皂草毒素蛋白或异株泻根毒蛋白;类固醇代谢酶,如3-羟基类固醇氧化酶、蜕皮类固醇-UDP-糖基-转移酶、胆固醇氧化酶、蜕皮激素抑制剂、HMG-COA-还原酶,离子通道阻断剂,如钠通道或钙通道阻断剂,保幼激素酯酶,利尿激素受体、茋合酶、联苄合酶、几丁质酶和葡聚糖酶。
在本发明的上下文中,δ-内毒素例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C,或营养期杀虫蛋白(Vip)例如Vip1、Vip2、Vip3或Vip3A应理解为显然还包括混合型毒素、截短的毒素和经修饰的毒素。混合型毒素是通过那些蛋白的不同结构域的新组合重组产生的(参见例如,WO 02/15701)。截短的毒素例如截短的Cry1Ab是已知的。在经修饰毒素的情况下,天然存在的毒素的一个或多个氨基酸被置换。在这样的氨基酸置换中,优选将非天然存在的蛋白酶识别序列插入毒素中,例如像在Cry3A055的情况下,组织蛋白酶-G-识别序列被插入Cry3A毒素中(参见WO 03/018810)。
这样的毒素或能够合成这样的毒素的转基因植物的实例披露于例如EP-A-0 374753、WO 93/07278、WO 95/34656、EP-A-0 427 529、EP-A-451 878以及WO 03/052073中。
用于制备这样的转基因植物的方法对于本领域技术人员是已知的并且描述在例如以上提及的公开物中。CryI型脱氧核糖核酸及其制备例如从WO 95/34656、EP-A-0 367474、EP-A-0 401 979以及WO 90/13651中已知。
包括在转基因植物中的毒素使得植物对有害昆虫有耐受性。这样的昆虫可以存在于任何昆虫分类群,但尤其常见于甲虫(鞘翅目)、双翅昆虫(双翅目)和蛾(鳞翅目)。
包含一个或多个编码杀虫剂抗性并且表达一种或多种毒素的基因的转基因植物是已知的并且其中一些是可商购的。(玉米品种,表达Cry1Ab毒素);YieldGard RootWO/>(玉米品种,表达Cry3Bb1毒素);YieldGard/>(玉米品种,表达Cry1Ab和Cry3Bb1毒素);/>(玉米品种,表达Cry9C毒素);Herculex/>(玉米品种,表达Cry1Fa2毒素和实现对除草剂草丁膦铵的耐受性的酶膦丝菌素N-乙酰转移酶(PAT));NuCOTN/>(棉花品种,表达Cry1Ac毒素);Bollgard/>(棉花品种,表达Cry1Ac毒素);Bollgard/>(棉花品种,表达Cry1Ac和Cry2Ab毒素);/>(棉花品种,表达Vip3A和Cry1Ab毒素);/>(马铃薯品种,表达Cry3A毒素);GT Advantage(GA21耐草甘膦性状),/>CBAdvantage(Bt11玉米螟(CB)性状)以及/>
这样的转基因作物的其他实例是:
1.Bt11玉米,来自Syngenta Seeds SAS[先正达种子公司],Chemin de l'Hobit[霍比特路]27,F-31 790St.Sauveur,France[圣苏维尔,法国],登记号C/FR/96/05/10。遗传修饰的玉蜀黍,通过转基因表达截短的Cry1Ab毒素,使之能抵抗欧洲玉米螟(玉米螟和粉茎螟)的侵袭。Bt11玉米还转基因地表达PAT酶以达到对除草剂草丁膦铵的耐受性。
2.Bt176玉米,来自Syngenta Seeds SAS[先正达种子公司],Chemin de l'Hobit[霍比特路]27,F-31 790St.Sauveur,France[圣苏维尔,法国],登记号C/FR/96/05/10。遗传修饰的玉蜀黍,通过转基因表达Cry1Ab毒素,使之能抵抗欧洲玉米螟(玉米螟和粉茎螟)的侵袭。Bt176玉米还转基因表达PAT酶以实现对除草剂草丁膦铵盐的耐受性。
3.MIR604玉米,来自Syngenta Seeds SAS[先正达种子公司],Chemin de l'Hobit[霍比特路]27,F-31 790St.Sauveur,France[圣苏维尔,法国],登记号C/FR/96/05/10。通过转基因表达经修饰的Cry3A毒素使之具有昆虫抗性的玉米。此毒素是通过插入组织蛋白酶-G-蛋白酶识别序列而经修饰的Cry3A055。此类转基因玉米植物的制备描述于WO 03/018810中。
4.MON 863玉米,来自Monsanto Europe S.A.[孟山都欧洲公司],270-272Avenuede Tervuren[特弗伦大道],B-1150Brussels,Belgium[布鲁塞尔,比利时],登记号C/DE/02/9。MON 863表达Cry3Bb1毒素,并且对某些鞘翅目昆虫有抗性。
5.IPC 531棉花,来自孟山都欧洲公司,270-272特弗伦大道,B-1150布鲁塞尔,比利时,登记号C/ES/96/02。
6.1507玉米,来自先锋海外公司(Pioneer Overseas Corporation),特德斯科大道(Avenue Tedesco),7B-1160布鲁塞尔,比利时,登记号C/NL/00/10。遗传改性的玉米,表达蛋白质Cry1F以获得对某些鳞翅目昆虫的抗性,并且表达PAT蛋白质以获得对除草剂草丁膦铵的耐受性。
7.NK603×MON 810玉米,来自Monsanto Europe S.A.[孟山都欧洲公司],270-272Avenue de Tervuren,B-1150Brussels,Belgium[特弗伦大道,B-1150布鲁塞尔,比利时],登记号C/GB/02/M3/03。通过将遗传修饰的品种NK603和MON 810杂交,由常规育种的杂交玉米品种构成。NK603×MON 810玉米转基因地表达由土壤杆菌属菌株CP4获得的蛋白质CP4 EPSPS,使之耐除草剂(含有草甘膦),以及由苏云金芽孢杆菌库尔斯塔克亚种获得的Cry1Ab毒素,使之耐某些鳞翅目昆虫,包括欧洲玉米螟。
抗昆虫的植物的转基因作物还描述于BATS(生物安全与可持续发展中心(Zentrumfür Biosicherheit und Nachhaltigkeit),BATS中心(Zentrum BATS),克拉斯崔舍(Clarastrasse)13,巴塞尔(Basel)4058,瑞士)报告2003(http://bats.ch)中。
术语“作物”应理解为还包括已经通过使用重组DNA技术而被这样转化使其能够合成具有选择性作用的抗病原物质的作物,这些抗病原物质是例如像所谓的“病程相关蛋白”(PRP,参见例如EP-A-0 392225)。这样的抗病原物质和能够合成这样的抗病原物质的转基因植物的实例例如从EP-A-0 392 225、WO 95/33818和EP-A-0 353 191是已知的。生产这样的转基因植物的方法对于本领域的普通技术人员而言通常是已知的并且描述于例如以上提及的公开物中。
作物也可以经修饰以增加对真菌(例如镰孢霉属、炭疽病或疫霉属)、细菌(例如假单胞菌属)或病毒(例如马铃薯卷叶病毒、番茄斑萎病毒、黄瓜花叶病毒)病原体的抗性。
作物还包括那些对线虫(如大豆异皮线虫)具有增加的抗性的作物。
具有对非生物性胁迫的耐受性的作物包括那些例如通过NF-YB或本领域中已知的其他蛋白质的表达对干旱、高盐、高温、寒冷、霜或光辐射具有增加的耐受性的作物。
可以由此类转基因植物表达的抗病原物质包括,例如,离子通道阻断剂(例如钠和钙通道阻断剂,像病毒的KP1、KP4或KP6毒素);芪合酶;联苄合酶;几丁质酶;葡聚糖酶;所谓的“病程相关蛋白”(PRP,参见例如EP-A-0 392 225);由微生物产生的抗病原物质,例如涉及植物病原体防御的肽抗生素或杂环类抗生素(参见例如WO 95/33818)或蛋白质或多肽因子(所谓的“植物疾病抗性基因”,如描述于WO 03/000906中的)。
根据本发明的组合物的其他使用范围是保护所储存的货物和储藏室以及保护原材料,如木材、纺织品、地板或建筑物,以及在卫生领域中,尤其是保护人类、家畜以及多产的牲畜免遭所提及类型的有害生物。
本发明还提供了用于控制有害生物(如蚊科和其他的疾病媒介物)的方法;也可参见http://www.who.int/malaria/vector_control/irs/en/)的方法。在一个实施例中,用于控制有害生物的方法包括通过涂刷、轧制、喷雾、涂布或浸渍,向目标有害生物、它们的场所或表面或基质施用本发明的组合物。通过举例,通过本发明的方法预期了表面(如墙、天花板或地板表面)的IRS(室内滞留喷雾)施用。在另一个实施例中,考虑到了将此类组合物施用于如下基底,如无纺或织物材料,该材料处于网织品、被覆物、被褥、窗帘以及帐篷的形式(或可以用于在这些物品的制造中使用)。
在一个实施例中,用于控制这样的有害生物的方法包括向目标有害生物、它们的场所或表面或基质施用杀有害生物有效量的本发明的组合物,以便于在该表面或基质上提供有效的滞留的杀有害生物活性。这样的施用可以通过涂刷、轧制、喷雾、涂布或浸渍本发明的杀有害生物组合物来进行。通过举例,通过本发明的方法预期了表面(如墙、天花板或地板表面)的IRS施用,以便于在该表面上提供有效的滞留的杀有害生物活性。在另一个实施例中,考虑了施用这样的组合物以用于在基底上的有害生物的残留控制,该基底是如处于网织品、被覆物、被褥、窗帘以及帐篷的形式(或可以用于在这些物品的制造中)的织物材料。
待处理的基质(包括无纺物、织物或网织品)可以由天然纤维,如棉花、拉菲亚树叶纤维、黄麻、亚麻、剑麻、粗麻布或羊毛,或者合成纤维,如聚酰胺、聚酯、聚丙烯、聚丙烯腈等等制成。聚酯是特别适合的。纺织品处理的方法是已知的,例如WO 2008/151984、WO 2003/034823、US 5631072、WO 2005/64072、WO 2006/128870、EP 1724392、WO 2005113886或WO2007/090739。
根据本发明的组合物的其他使用范围是针对所有观赏树木连同所有种类的果树和坚果树的树木注射/树干处理领域。
在树木注射/树干处理领域中,根据本发明的这些化合物特别适合于对抗来自上述的鳞翅目和来自鞘翅目的钻木昆虫,尤其是对抗下表A和B中列出的钻木虫:
表A.具有经济重要性的外来钻木虫的实例。
表B.具有经济重要性的本地钻木虫的实例。
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本发明也可以用于控制任何可以存在于草坪草中的昆虫有害生物,包括例如甲虫、毛虫、火蚁、地面珍珠(ground pearl)、千足虫、潮虫、螨虫、蝼蛄、介壳虫、粉蚧蜱、沫蝉、南方麦小蝽以及蛴螬。本发明可以用于控制处于其生命周期的各个阶段的昆虫有害生物,包括卵、幼虫、若虫和成虫。
具体而言,本发明可以用于控制取食草坪草的根部的昆虫有害生物,这些昆虫有害生物包括蛴螬(如圆头犀金龟属(Cyclocephala spp.)(例如蒙面金龟子,C.lurida)、Rhizotrogus属(例如欧洲金龟子,欧洲切根鳃金龟(R.majalis))、黄栌属(Cotinus spp.)(例如绿六月甲虫(Green June beetle),C.nitida)、弧丽金龟属(Popillia spp.)(例如日本甲虫,龟纹瓢虫(P.japonica))、鳃角金龟属(Phyllophaga spp.)(例如五月/六月甲虫)、Ataenius属(例如草坪草黑金龟(Black turfgrass ataenius),A.spretulus)、绒毛金龟属(Maladera spp.)(例如亚洲花园甲虫(Asiatic garden beetle),M.castanea)以及Tomarus属),地面珍珠(硕蚧属(Margarodes spp.)),蝼蛄(褐黄色的、南方的、以及短翅的;痣蟋蟀属(Scapteriscus spp.),非洲蝼蛄(Gryllotalpa africana))以及大蚊幼虫(leatherjackets)(欧洲大蚊(European crane fly),大蚊属(Tipula spp.))。
本发明还可以用于控制茅草住宅的草坪草的昆虫有害生物,这些昆虫有害生物包括粘虫(如秋夜蛾(fall armyWO rm)草地贪夜蛾(Spodoptera frugiperda),和常见夜蛾一星黏虫(Pseudaletia unipuncta))、切根虫,象鼻虫(尖隐喙象属(Sphenophorus spp.),如S.venatus verstitus和牧草长喙象(S.parvulus))以及草地螟(如草螟属(Crambus spp.)和热带草地螟,Herpetogramma phaeopteralis)。
本发明还可以用于控制在地上生活并取食草坪草叶子的草坪草中的昆虫有害生物,这些昆虫有害生物包括麦小蝽(如南方麦小蝽,南方杆长蝽(Blissus insularis))、狗牙根螨(Bermudagrass mite)(Eriophyes cynodoniensis)、盖氏虎尾草粉蚧(草竹粉蚧(Antonina graminis))、两线沫蝉(Propsapia bicincta)、叶蝉、切根虫(夜蛾科)、以及麦二叉蚜。
本发明还可以用于控制草坪草中的其他有害生物,如在草坪中创建蚁巢的外引红火蚁(红火蚁(Solenopsis invicta))。
在卫生领域中,根据本发明的组合物是有效地对抗外寄生虫如硬蜱、软蜱、疥螨、秋螨、蝇(叮咬和舔舐)、寄生性蝇幼虫,虱、发虱、鸟虱和跳蚤。
这样的寄生虫的实例是:
虱目:血虱属、长颚虱属、人虱属和阴虱属、盲虱属。
食毛目:毛羽虱属、短角鸟虱属、鸭虱属、牛羽虱属、Werneckiella属、Lepikentron属、畜虱属、啮毛虱属以及猫羽虱属。
双翅目及长角亚目和短角亚目,例如伊蚊属、按蚊属、库蚊属、蚋属、真蚋属、白蛉属、罗蛉属、库蠓属、斑虻属、驼背虻属、黄虻属、虻属、麻虻属、Philipomyia属、蜂虱蝇属、家蝇属、齿股蝇属、螫蝇属、黑角蝇属、莫蝇属、厕蝇属、舌蝇属、丽蝇属、绿蝇属、金蝇属、污蝇属、麻蝇属、狂蝇属、皮蝇属、胃蝇属、虱蝇属、羊虱蝇属和蜱蝇属。
蚤目,例如蚤属、栉头蚤属、客蚤属、角叶蚤属。
异翅目,例如臭虫属、锥鼻虫属属、红猎蝽属、锥蝽属。
蜚蠊目,例如东方蜚蠊、美洲大蠊、德国小蠊以及夏柏拉蟑螂属。
蜱螨亚纲(螨科)和后气门目和中气门目,例如锐缘蜱属、钝缘蜱属、耳蜱属、硬蜱属、钝眼蜱属、牛蜱属、革蜱属、血蜱属、璃眼蜱属、扇头蜱属、皮刺螨属、刺利螨属、肺刺螨属、胸刺螨属和瓦螨属。
轴螨目(前气门亚目)和粉螨目(无气门亚目),例如蜂盾螨属、姬螯属、禽螯螨属、肉螨属、疮螨属、蠕形螨属、恙螨属、牦螨属、粉螨属、食酪螨属、嗜木螨属、颈下螨属、翅螨属、痒螨属、皮螨属、耳疥螨属、疥螨属、耳螨属、鸟疥螨属、胞螨属以及鸡雏螨属。
根据本发明的组合物还适用于保护材料如木材、纺织品、塑料、粘合剂、胶、漆料、纸张和卡片、皮革、地板和建筑等免受昆虫侵染。
根据本发明的组合物可以用于例如对抗以下有害生物:甲虫,如北美家天牛、长毛天牛、家具窃蠹、红毛窃蠹、梳角细脉窃蠹、石斛、松芽枝窃蠹、松产品窃蠹、褐粉蠹、非洲粉蠹、南方粉蠹、栎粉蠹、柔毛粉蠹、胸粉蠹、鳞毛粉蠹、材小蠹属、条木小蠹属、咖啡黑长蠹、树长蠹、棕异翅长蠹、双棘长蠹属与竹长蠹;以及膜翅类昆虫,如蓝黑树蜂、云杉大树蜂、泰加大树蜂与大树蜂;以及白蚁,如欧洲木白蚁、麻头堆砂白蚁、印巴结构木异白蚁、黄胸散白蚁、桑特散白蚁、散白蚁、达尔文澳白蚁、内华达古白蚁与家白蚁;以及蛀虫,如衣鱼。
根据本发明的化合物可以按未经修饰的形式用作杀有害生物剂,但它们通常以多种方式使用配制佐剂(如载体、溶剂以及表面活性物质)被配制成组合物。这些配制品可以处于不同的实体形式,例如,处于以下形式:撒粉剂、凝胶、可湿性粉剂、水可分散性颗粒剂、水可分散性片剂、泡腾压缩片剂、可乳化的浓缩物、微可乳化浓缩物、水包油乳剂、可流动油、水性分散体、油性分散体、悬乳剂、胶囊悬浮液、可乳化的颗粒剂、可溶性液体、水可溶性浓缩物(以水或水混溶性有机溶剂作为载体)、浸渍的聚合物膜或处于已知的其他形式,例如从关于杀有害生物剂的FAO和WHO标准的发展和使用的手册(Manual on Developmentand Use of FAO and WHO Specifications for Pesticides),联合国,第1版,二次修订(2010)中已知的。此类配制品可以直接使用或者可以使用前稀释再使用。可以利用例如水、液体肥料、微量营养素、生物有机体、油或溶剂来稀释。
可以通过例如将活性成分与配制品佐剂混合来制备这些配制品以便获得处于精细分散固体、颗粒、溶液、分散体或乳剂形式的组合物。这些活性成分还可以与其他佐剂(例如精细分散固体、矿物油、植物或动物的油、改性的植物或动物的油、有机溶剂、水、表面活性物质或它们的组合)来一起配制。
这些活性成分还可以被包含于非常精细的微胶囊中。微胶囊在多孔载体中含有这些活性成分。这使这些活性成分能以受控的量(例如,缓慢释放)释放到环境中。微胶囊通常具有从0.1到500微米的直径。它们包含的活性成分的量按重量计是胶囊重量的约从25%至95%。这些活性成分可以处于整体性的固体的形式、处于固体或液体分散体中的精细颗粒的形式或处于合适溶液的形式。包囊的膜可以包括例如天然的或合成的橡胶、纤维素、苯乙烯/丁二烯共聚物、聚丙烯腈、聚丙烯酸酯、聚酯、聚酰胺、聚脲、聚氨酯或化学改性的聚合物以及淀粉黄原酸盐、或本领域技术人员已知的其他聚合物。可替代地,可以形成非常精细的微胶囊,其中活性成分在基础物质的固体基质中是以精细分散颗粒的形式被包含的,但这些微胶囊本身未经包裹。
适合于制备根据本发明所述的这些组合物的配制佐剂本身是已知的。作为液体载体可以使用:水、甲苯、二甲苯、石油醚、植物油、丙酮、甲基乙基酮、环己酮、酸酐、乙腈、乙酰苯、乙酸戊酯、2-丁酮、碳酸丁烯酯、氯苯、环己烷、环己醇、乙酸烷基酯的乙酸、二丙酮醇、1,2-二氯丙烷、二乙醇胺、对-二乙基苯、二甘醇、松脂酸二乙二醇酯、二甘醇丁基醚、二甘醇乙基醚、二甘醇甲醚、N,N-二甲基甲酰胺、二甲基亚砜、1,4-二噁烷、二丙二醇、二丙二醇甲基醚、双丙甘醇二苯甲酸酯、二丙二醇、烷基吡咯烷酮、乙酸乙酯、2-乙基己醇、碳酸乙烯酯、1,1,1-三氯乙烷、2-庚酮、α-蒎烯、d-苧烯、乳酸乙酯、乙二醇、乙二醇丁基醚、乙二醇甲基醚、γ-丁内酯、丙三醇、乙酸甘油酯、二乙酸甘油酯、三乙酸甘油酯、十六烷、己二醇、乙酸异戊基酯、乙酸异冰片基酯、异辛烷、异佛尔酮、异丙苯、肉豆蔻酸异丙酯、乳酸、月桂胺、异亚丙基丙酮、甲氧基丙醇、甲基异戊基酮、甲基异丁基酮、月桂酸甲酯、辛酸甲酯、油酸甲酯、二氯甲烷、间二甲苯、正己烷、正辛胺、十八烷酸、辛胺乙酸酯、油酸、油烯基胺、邻二甲苯、苯酚、聚乙二醇、丙酸、乳酸丙酯、碳酸亚丙酯、丙二醇、丙二醇甲基醚、对-二甲苯、甲苯、磷酸三乙酯、三乙二醇、二甲苯磺酸、石蜡、矿物油、三氯乙烯、全氯乙烯、乙酸乙酯、乙酸戊酯、乙酸丁酯、丙二醇甲基醚、二乙二醇甲基醚、甲醇、乙醇、异丙醇以及更高分子量的醇,例如戊醇、四氢呋喃醇、己醇、辛醇、乙二醇、丙二醇、甘油、N-甲基-2-吡咯烷酮等。
适合的固体载体是,例如滑石、二氧化钛、叶蜡石粘土、硅石、凹凸棒石粘土、硅藻土、石灰石、碳酸钙、膨润土、钙蒙脱土、棉籽壳、小麦粉、大豆粉、浮石、木粉、胡桃壳粉、木素和类似的物质。
许多表面活性物质可以有利地用于固体和液体配制品两者中,尤其是在使用前可被载体稀释的那些配制品中。表面活性物质可以是阴离子的、阳离子的、非离子的或聚合的并且它们可以用作乳化剂、湿润剂或悬浮剂或用于其他目的。典型的表面活性物质包括例如烷基硫酸酯的盐,如十二烷基硫酸二乙醇铵;烷基芳基磺酸酯的盐,如十二烷基苯磺酸钙;烷基酚/氧化烯加成产物,如乙氧基化壬基苯酚;醇/氧化烯加成产物,如乙氧基化十三烷醇;皂,如硬脂酸钠;烷基萘磺酸酯的盐,如二丁基萘磺酸钠;磺基丁二酸二烷基酯的盐,如二(2-乙基己基)磺基丁二酸钠;山梨糖醇酯,如山梨糖醇油酸酯;季铵,如氯化十二烷基三甲基铵;脂肪酸的聚乙二醇酯,如聚乙二醇硬脂酸酯;环氧乙烷和环氧丙烷的嵌段共聚物;以及磷酸单-和二-烷酯的盐;以及还有其他物质,例如描述于:McCutcheon'sDetergents and Emulsifiers Annual[麦卡琴清洁剂和乳化剂年鉴],MC PublishingCorp.[MC出版公司],RidgeWO od New Jersey[里奇伍德新泽西州](1981)。
可以用于杀有害生物配制品的其他佐剂包括结晶作用抑制剂、粘度调剂剂、助悬剂、染料、抗氧化剂、发泡剂、光吸收剂、混合助剂、消泡剂、络合剂、中和或改变pH的物质与缓冲液、腐蚀抑制剂、香料、湿润剂、吸收增强剂、微量营养素、增塑剂、助流剂、润滑剂、分散剂、增稠剂、防冻剂、杀微生物剂、以及液体与固体肥料。
根据本发明的组合物可以包括添加剂,该添加剂包括植物或动物来源的油、矿物油、此类油的烷基酯或此类油与油衍生物的混合物。在根据本发明的组合物中的油添加剂的量通常是该待施用的混合物的0.01%到10%。例如,可以在喷雾混合物已经制备以后将该油添加剂以所希望的浓度加入喷雾罐中。优选的油添加剂包括矿物油或植物来源的油,例如菜籽油、橄榄油或葵花籽油;乳化的植物油;植物来源的油的烷基酯,例如甲基衍生物;或动物来源的油,如鱼油或牛脂。优选的油添加剂包括C8-C22脂肪酸的烷基酯,尤其是C12-C18脂肪酸的甲基衍生物,例如月桂酸、棕榈酸以及油酸的甲基酯(分别为月桂酸甲酯、棕榈酸甲酯和油酸甲酯)。许多油衍生物获知于以下文献:Compendium of HerbicideAdjuvants,10th Edition,Southern Illinois University,2010[除草剂佐剂纲要,第10版,南伊利诺伊大学,2010]。
这些本发明组合物总体上包括按重量计从0.1%至99%,尤其是按重量计从0.1%至95%的本发明的化合物以及按重量计从1%至99.9%的配制佐剂,该配制佐剂优选地包括按重量计从0至25%的表面活性物质。而商用产品可以优选地被配制为浓缩物,最终使用者将通常使用稀释配制品。
施用比率在宽范围之内变化并且取决于土壤的性质、施用方法、作物植物、待控制的有害生物、主要气候条件、以及受施用方法支配的其他因素、施用时间以及目标作物。一般来讲,可以将化合物以从1l/ha至2000l/ha,尤其是从10l/ha到1000l/ha的比率施用。
优选的配制品可以具有以下成分(重量%):
可乳化的浓缩物:
活性成分:1%至95%,优选60%至90%
表面活性剂:1%至30%,优选5%至20%
液体载体:1%至80%,优选1%至35%
尘剂:
活性成分:0.1%至10%,优选0.1%至5%
固体载体:99.9%至90%,优选99.9%至99%
悬浮液浓缩剂:
活性成分:5%至75%,优选10%至50%
水:94%至24%,优选88%至30%
表面活性剂:1%至40%,优选2%至30%
可湿性粉剂:
活性成分:0.5%至90%,优选1%至80%
表面活性剂:0.5%至20%,优选1%至15%
固体载体:5%至95%,优选15%至90%
颗粒剂:
活性成分:0.1%至30%,优选0.1%至15%
固体载体:99.5%至70%,优选97%至85%
以下实例进一步阐述了(但不限制)本发明:
可湿性粉剂 | a) | b) | c) |
活性成分 | 25% | 50% | 75% |
木质素磺酸钠 | 5% | 5% | - |
月桂基硫酸钠 | 3% | - | 5% |
二异丁基萘磺酸钠 | - | 6% | 10% |
苯酚聚乙二醇醚(7-8mol的环氧乙烷) | - | 2% | - |
高度分散的硅酸 | 5% | 10% | 10% |
高岭土 | 62% | 27% | - |
将该组合与这些佐剂充分混合并且将混合物在适当的研磨机中充分研磨,从而给出可以用水稀释而给出所希望的浓度的悬浮液的可湿性粉剂。
干种子处理用的粉剂 | a) | b) | c) |
活性成分 | 25% | 50% | 75% |
轻质矿物油 | 5% | 5% | 5% |
高度分散的硅酸 | 5% | 5% | - |
高岭土 | 65% | 40% | - |
滑石 | - | 20% |
将该组合与佐剂充分混合并且将该混合物在适合的研磨机中充分研磨,从而给出可以直接用于种子处理的粉剂。
可乳化浓缩剂 | |
活性成分 | 10% |
辛基苯酚聚乙二醇醚(4-5mol的环氧乙烷) | 3% |
十二烷基苯磺酸钙 | 3% |
蓖麻油聚乙二醇醚(35mol环氧乙烷) | 4% |
环己酮 | 30% |
二甲苯混合物 | 50% |
在植物保护中可以使用的具有任何所要求的稀释度的乳液可以通过用水稀释从这种浓缩物获得。
尘剂 | a) | b) | c) |
活性成分 | 5% | 6% | 4% |
滑石 | 95% | - | - |
高岭土 | - | 94% | - |
矿物填充剂 | - | - | 96% |
通过将该组合与载体混合并且将混合物在适当的研磨机中研磨获得立即可用的尘剂。此类粉剂还可以用于种子的干拌种。
挤出机颗粒剂 | |
活性成分 | 15% |
木质素磺酸钠 | 2% |
羧甲基纤维素 | 1% |
高岭土 | 82% |
将该组合与这些佐剂混合并且研磨,并且将混合物用水湿润。将混合物挤出并且然后在空气流中干燥。
包衣的颗粒剂 | |
活性成分 | 8% |
聚乙二醇(mol.wt.200) | 3% |
高岭土 | 89% |
将这种精细研磨的组合在混合器中均匀地施用于用聚乙二醇湿润的高岭土中。以此方式获得无尘的包衣的颗粒剂。
悬浮液浓缩剂
活性成分 | 40% |
丙二醇 | 10% |
壬基酚聚乙二醇醚(15mol的环氧乙烷) | 6% |
木质素磺酸钠 | 10% |
羧甲基纤维素 | 1% |
硅油(处于在水中75%的乳液的形式) | 1% |
水 | 32% |
将精细研磨的组合与佐剂密切混合,从而给出悬浮液浓缩剂,可以通过使用水稀释从该浓缩剂获得任何所希望稀释度的悬浮液。使用这样的稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷洒、倾倒或浸渍进行保护。
种子处理用的可流动性浓缩剂
活性成分 | 40% |
丙二醇 | 5% |
共聚物丁醇PO/EO | 2% |
三苯乙烯酚,具有10-20摩尔EO | 2% |
1,2-苯并异噻唑啉-3-酮(处于在水中20%的溶液形式) | 0.5% |
单偶氮-颜料钙盐 | 5% |
硅油(处于在水中75%的乳液形式) | 0.2% |
水 | 45.3% |
将精细研磨的组合与佐剂密切混合,从而给出悬浮液浓缩剂,可以通过使用水稀释从该浓缩剂获得任何所希望稀释度的悬浮液。使用这样的稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷洒、倾倒或浸渍进行保护。
缓释的胶囊悬浮剂
将28份的组合与2份的芳香族溶剂以及7份的甲苯二异氰酸酯/多亚甲基-聚苯基异氰酸酯-混合物(8:1)进行混合。将此混合物在1.2份的聚乙烯醇、0.05份的消泡剂以及51.6份的水的混合物中进行乳化直至达到所希望的颗粒尺寸。向此乳液中添加2.8份的1,6-己二胺于5.3份的水中的混合物。将该混合物搅拌直至聚合反应完成。将获得的胶囊悬浮液通过添加0.25份的增稠剂以及3份的分散剂进行稳定。该胶囊悬浮液配制品包含28%的活性成分。该介质胶囊的直径是8微米-15微米。将所得配制品作为适用于此目的装置中的水性悬浮液施用到种子上。
配制品类型包括乳液浓缩剂(EC)、悬浮液浓缩物(SC)、悬乳剂(SE)、胶囊悬浮剂(CS)、水可分散性颗粒剂(WG)、可乳化性颗粒剂(EG)、油包水型乳液(EO)、水包油型乳液(EW)、微乳液(ME)、油分散体(OD)、油悬剂(OF)、油溶性液剂(OL)、可溶性浓缩剂(SL)、超低容量悬浮剂(SU)、超低容量液剂(UL)、母药(TK)、可分散性浓缩剂(DC)、可湿性粉剂(WP)、可溶性颗粒剂(SG)或与农业上可接受的佐剂组合的任何技术上可行的配制品。
制备实例:
“Mp”是指以℃计的熔点。自由基表示甲基基团。1H NMR测量值在Brucker 400MHz分光计上记录,化学位移相对于TMS标准品以ppm给出。光谱在如指定的氘代溶剂中测量。用以下LCMS方法中的任一种来表征这些化合物:对于每种化合物获得的特征LCMS值是保留时间(“Rt”以分钟为单位记录)和测量的分子离子(M+H)+或(M-H)-。
LCMS方法:
方法1:标准1。
在来自沃特斯(Waters)的质谱仪(SQD、SQDII单四极杆质谱仪)上记录光谱,该质谱仪配备有电喷射源(极性:正离子和负离子,毛细管:3.00kV,锥孔范围:30V,萃取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:50l/h,去溶剂化气体流量:650l/h;质量范围:100Da至900Da)以及一个来自沃特斯的Acquity UPLC:二元泵、加热管柱室、二极管阵列检测器以及ELSD检测器)。柱:沃特斯UPLC HSS T3,1.8μm,30×2.1mm,温度:60℃;DAD波长范围(nm):210至500,溶剂梯度:A=水+5% MeOH+0.05%HCOOH,B=乙腈+0.05% HCOOH;梯度:10%-100% B,在1.2min内;流量(ml/min)0.85。
方法2:标准长
在来自沃特斯的质谱仪(SQD、SQDII单四极杆质谱仪)上记录光谱,该质谱仪配备有电喷射源(极性:正离子和负离子,毛细管:3.00kV,锥孔范围:30V,萃取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:50l/h,去溶剂化气体流量:650l/h;质量范围:100Da至900Da)以及一个来自沃特斯的Acquity UPLC:二元泵、加热管柱室、二极管阵列检测器以及ELSD检测器)。柱:沃特斯UPLC HSS T3,1.8μm,30×2.1mm,温度:60℃;DAD波长范围(nm):210至500,溶剂梯度:A=水+5% MeOH+0.05%HCOOH,B=乙腈+0.05% HCOOH;梯度:10%-100% B,在2.7min内;流量(ml/min)0.85。
方法3:标准2长
在来自安捷伦科技(Agilent Technologies)的质谱仪(6410三重四极杆质谱仪)上记录光谱,该质谱仪配备有电喷射源(极性:正和负极转换:毛细管:4.00kV,碎裂电压:100.00V,气体温度:350℃,气体流量:11L/min,喷雾器气体:45psi,质量范围:110-1000Da,DAD波长范围:210-400nm)。柱:KINETEX EVO C18,长度50mm,直径4.6mm,粒度2.6μm。柱烘箱温度40℃。溶剂梯度:A=具有0.1%甲酸:乙腈(95:5v/v)的水B=具有0.1%甲酸的乙腈。梯度=0min 90% A,10% B;0.9-1.8min 0% A,100% B,2.2-2.5min 90% A,10% B。流速:1.8mL/min。
方法4:标准2
在来自沃特斯的质谱仪(Acquity SDS质谱仪)上记录光谱,该质谱仪配备有电喷射源(极性:正和负极转换:毛细管:3.00kV,锥孔电压:41.00V,源温度:150℃,去溶剂化气体流量:1000L/Hr,去溶剂化温度:500℃,锥孔气体流量:50L/hr,质量范围:110-800Da,PDA波长范围:210-400nm)。柱:Acquity UPLC HSS T3 C18,长度30mm,直径2.1mm,粒度1.8μm。柱烘箱温度40℃。溶剂梯度:A=具有0.1%甲酸:乙腈(95:5v/v)的水B=具有0.05%甲酸的乙腈。梯度=0min 90% A,10% B;0.2min 50% A,50% B;0.7-1.3min 0% A,100% B;1.4-1.6min 90% A,10% B。流速:0.8mL/min。
实例P1:2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]- 3-吡啶基]-2-甲基-丙二腈(化合物P1)的制备
步骤1:2-[5-乙基硫烷基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]丙二腈(化合物P7)的制备
向微波小瓶中加入2-(5-溴-3-乙基硫烷基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(根据WO 16096584制备)(5.00g,12.0mmol)、丙二腈(0.830ml,13.2mmol,1.10当量)、氢氧化钾(2.02g,36.0mmol,3.00当量)和双(三苯磷)钯(II)二氯化物(420mg,0.60mmol,0.05当量)。在添加N-甲基-吡咯烷酮(24mL)后,将反应混合物用氩气脱气5min。将容器密封并在130℃的油浴中加热过夜。在冷却至室温后,将反应混合物倒入水中,用2MHCl小心地酸化pH,并将水相用乙酸乙酯萃取两次。将合并的有机相用水洗涤两次,并将这些合并的水相再次用二氯甲烷萃取三次。从合并的二氯甲烷相中沉淀出固体,将其过滤。将乙酸乙酯和二氯甲烷两者有机相合并、经硫酸钠干燥、过滤并在真空下浓缩。将粗制的深棕色油通过硅胶柱层析、用纯乙酸乙酯洗脱进行纯化。将所选级分蒸发以产生呈棕色固体的标题化合物。LCMS(方法1):403(M+H)+;保留时间:0.86min。
步骤2:2-[5-乙基硫烷基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]-2-甲基-丙二腈(化合物P8)的制备
在氩气氛下,向2-[5-乙基硫烷基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]丙二腈(9.58g,10.7mmol)在N,N-二甲基甲酰胺(32ml)中的溶液中添加碳酸钾(1.58g,11.3mmol,1.05当量),随后逐滴添加甲基碘(1.00ml,16.1mmol,1.50当量)。将所得棕色混合物在40℃下搅拌2小时。另外添加碳酸钾(148mg,1.07mmol,0.10当量)和甲基碘(1.00ml,16.1mmol,1.50当量),并且将反应混合物进一步在40℃下加热3小时。反应完成之后,将反应混合物冷却至室温并用水稀释。将水相用2M HCl轻微酸化,并用乙酸乙酯萃取两次。将合并的有机相用水洗涤四次、经硫酸钠干燥,进行过滤并进行浓缩。使残余物经受硅胶柱层析、用二氯甲烷中的乙酸乙酯洗脱,以产生呈黄褐色固体的标题化合物。LCMS(方法1):417(M+H)+;保留时间:1.01min。
步骤3:2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]-2-甲基-丙二腈(化合物P1)的制备
在氩气氛下,在0℃下,向2-[5-乙基硫烷基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]-2-甲基-丙二腈(100mg,0.24mmol)在二氯甲烷(30ml)中的溶液中添加3-氯过苯甲酸(91mg,0.53mmol,2.2当量)。在0℃下搅拌30min后,然后在室温下搅拌1小时后,通过倾入饱和硫代硫酸钠溶液来缓慢地淬灭反应混合物。将该水相用乙酸乙酯萃取两次、将这些合并的有机相经硫酸钠干燥、过滤并进行浓缩。将粗物质首先在二异丙基醚中进行研磨,并且将所得白色固体通过硅胶柱层析、用二氯甲烷中的乙酸乙酯洗脱来进一步纯化,以给出呈白色固体的标题化合物。LCMS(方法1):449(M+H)+;保留时间:0.95min。
实例P2:2-[5-乙基磺酰基-6-[7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪-6-基]-
3-吡啶基]-2-甲基-丙腈(化合物P2)的制备
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步骤1:5-(1-氰基-1-甲基-乙基)-3-乙基磺酰基-吡啶-2-甲酸甲基酯的制备
在氩气下,将5-(氰基甲基)-3-乙基磺酰基-吡啶-2-甲酸甲基酯(根据WO16096584制备)(1.40g,5.22mmol)溶解在DMF(21ml)中。将反应混合物冷却至0℃,并且分部分地添加氢化钠((480mg,12.5mmol,2.40当量)。在0℃下,将深红色反应混合物搅拌30min。在0℃下经由注射器将反应混合物添加到甲基碘(0.78ml,12.5mmol,2.40当量)在DMF(21ml)中的溶液中。允许所得混合物缓慢加温至室温并搅拌过夜。在该反应完成后,将混合物倒入饱和水性氯化铵溶液中,并将水相用乙酸乙酯进行萃取。将有机相用水并且然后用盐水来洗涤四次,经硫酸钠干燥,过滤并进行浓缩。将粗物质通过硅胶柱层析、用环己烷中的乙酸乙酯洗脱来进行纯化,以产生呈白色固体的标题化合物。LCMS(方法1):297(M+H)+;保留时间:0.77min。
步骤2:5-(1-氰基-1-甲基-乙基)-3-乙基磺酰基-吡啶-2-甲酸的制备
将5-(1-氰基-1-甲基-乙基)-3-乙基磺酰基-吡啶-2-甲酸甲基酯(1.40g,4.72mmol)溶解在四氢呋喃(40ml)和水(13ml)中。添加氢氧化锂(170mg,7.09mmo,1.50当量),并将反应混合物在室温下搅拌过夜。将反应混合物浓缩,并将含水残余物的pH用1MHCl调节到pH1。过滤所得白色悬浮液,将固体用最少量的冷水洗涤并在真空中干燥,给出所希望的产物。将该化合物不进行进一步纯化而直接用在下一步骤中。LCMS(方法1):283(M+H)+;保留时间:0.42min。
步骤3:5-(1-氰基-1-甲基-乙基)-3-乙基磺酰基-吡啶-2-甲酰氯的制备
在氩气下,将5-(1-氰基-1-甲基-乙基)-3-乙基磺酰基-吡啶-2-甲酸(1.02g,3.61mmol)与催化量的N,N-二甲基甲酰胺一起溶解在二氯甲烷(24ml)中。经由注射器逐滴添加草酰氯(0.47ml,5.42mmol,1.50当量)。将反应混合物在回流下加热3小时。冷却至室温后,将反应混合物蒸发至干。将所得棕色油直接用于下一步骤。
步骤4:5-(1-氰基-1-甲基-乙基)-3-乙基磺酰基-N-[3-(甲基氨基)-6-(三氟甲基)哒嗪-4-基]吡啶-2-甲酰胺的制备
将N-3-甲基-6-(三氟甲基)哒嗪-3,4-二胺(根据WO 2016/116338制备)(150mg,0.78mmol)与N,N’-二异丙基乙基胺一起溶解在四氢呋喃(5.0ml)中。将反应混合物冷却至0℃,并逐滴添加5-(1-氰基-1-甲基-乙基)-3-乙基磺酰基-吡啶-2-碳酰氯(258mg,1.1当量)在四氢呋喃(5.0ml)中的溶液中。将反应混合物缓慢加温至室温并搅拌过夜。通过添加饱和水性氯化铵溶液来缓慢地淬灭反应,并将水相用乙酸乙酯萃取三次。将合并的有机相用水、盐水洗涤,经硫酸钠进行干燥,过滤并进行浓缩。将粗物质不经纯化而直接用于下一步骤。LCMS(方法1):425(M+H)+;保留时间:1.03min。
步骤5:2-[5-乙基磺酰基-6-[7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪-6-基]-3-吡啶基]-2-甲基-丙腈的制备
将5-(1-氰基-1-甲基-乙基)-3-乙基磺酰基-N-[3-(甲基氨基)-6-(三氟甲基)哒嗪-4-基]吡啶-2-甲酰胺(250mg,0.55mmol)溶解在乙酸(1.64ml)中,并且将反应混合物加热至100℃持续5小时。将反应混合物浓缩,并将残余物用甲苯蒸发以去除过量的乙酸。将粗物质通过硅胶柱层析、用环己烷溶液中的乙酸乙酯洗脱来进行纯化,随后在二乙醚中进行研磨,以产生呈白色固体的标题化合物。LCMS(方法1):439(M+H)+;保留时间:0.93min。
实例P3:2-乙基-2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡
啶-2-基]-3-吡啶基]丁腈(化合物P3)的制备
步骤1:2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]乙腈的制备
向微波小瓶中加入2-(5-溴-3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(根据WO 16096584制备)(6.00g,13.4mmol)在N,N-二甲基甲酰胺(27ml)中的溶液。在氩气氛下,向这个溶液添加三甲基甲硅烷基-乙腈(2.77ml,20.0mmol,1.50当量)、氟化锌(837mg,8.01mmol,0.60当量)、xantphos(315mg,0.53mmol,0.04当量)和Pd2(dba)3(250mg,0.27mmol,0.02当量)。将小瓶密封并在微波体系中在140℃下加热30min。将反应混合物用乙酸乙酯稀释,用水洗涤三次并用盐水洗涤一次。将有机层经硫酸钠干燥、过滤并进行浓缩。将粗物质通过硅胶柱层析、用二氯甲烷中的甲醇洗脱来进行纯化,以产生呈白色固体的标题化合物。LCMS(方法1):410(M+H)+;保留时间:0.86min。
步骤2:2-乙基-2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]丁腈的制备
在氩气下,将2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]乙腈(500mg,1.22mmol)溶解在N,N-二甲基甲酰胺(5ml)中。将反应混合物冷却至0℃。分部分地小心添加氢化钠(66mg,1.71mmol,1.40当量)。将深红色反应混合物在0℃下搅拌30min。在氩气下,0℃下,经由注射器将获得的溶液添加到乙基碘(0.137ml,1.71mmol,1.40当量)在DMF(5ml)中的溶液中。将所得混合物缓慢加温至室温并搅拌过夜。然后将该混合物缓慢地倒入饱和水性氯化铵溶液中,并将水相用乙酸乙酯进行萃取。将有机相用水、然后用盐水来洗涤四次,经硫酸钠干燥,过滤并进行浓缩。将粗物质通过硅胶柱层析、用环己烷中的乙酸乙酯洗脱来进行纯化,以产生呈白色固体的标题化合物。LCMS(方法1):466(M+H)+;保留时间:1.02min。
实例P4:2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-
3-吡啶基]丁腈(化合物P4)的制备
在氩气下,将2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]乙腈(如实例P3的步骤1中所描述的制备)(500mg,1.22mmol)溶解在N,N-二甲基甲酰胺(5ml)中。将反应混合物冷却至0℃。分部分地小心添加氢化钠(66mg,1.71mmol,1.40当量)。将深红色反应混合物在0℃下搅拌30min。在氩气下,0℃下,将获得的反应混合物逐滴添加到乙基碘(0.137ml,1.71mmol,1.40当量)在DMF(5ml)中的溶液中。将所得混合物缓慢加温至室温并搅拌过夜。然后将该混合物缓慢地倒入饱和水性氯化铵溶液中,并将水相用乙酸乙酯进行萃取。将有机相用水、然后用盐水来洗涤四次,经硫酸钠干燥,过滤并进行浓缩。将粗物质通过硅胶柱层析、用环己烷中的乙酸乙酯洗脱来进行纯化,以产生呈白色固体的标题化合物。LCMS(方法1):438(M+H)+;保留时间:0.94min。
实例P5:2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-
3-吡啶基]-2-甲基-丙腈(化合物P5)的制备
在氩气下,将2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]乙腈(如实例P3的步骤1中所描述的制备)(400mg,0.98mmol)溶解在N,N-二甲基甲酰胺(4ml)中。将反应混合物冷却至0℃。分部分地小心添加氢化钠(52mg,1.37mmol,1.40当量)。将深红色反应混合物在0℃下搅拌30min。在氩气下,0℃下,将获得的混合物添加到甲基碘(0.085ml,1.37mmol,1.40当量)在DMF(4ml)中的溶液中。将所得混合物缓慢加温至室温并搅拌过夜。然后将该混合物缓慢地倒入饱和水性氯化铵溶液中,并将水相用乙酸乙酯进行萃取。将有机相用水、然后用盐水来洗涤四次,经硫酸钠干燥,过滤并进行浓缩。将粗物质通过硅胶柱层析、用环己烷中的乙酸乙酯洗脱来进行纯化,以产生呈白色固体的标题化合物。LCMS(方法1):438(M+H)+;保留时间:0.93min。
实例P6:2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-
3-吡啶基]丙腈(化合物P6)的制备
在氩气下,将22-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]乙腈(如实例P3的步骤1中所描述的制备)(400mg,0.98mmol)溶解在N,N-二甲基甲酰胺(4ml)中。将反应混合物冷却至0℃。分部分地小心添加氢化钠(52mg,1.37mmol,1.40当量)。将深红色反应混合物在0℃下搅拌30min。在氩气下,0℃下,将获得的混合物添加到甲基碘(0.085ml,1.37mmol,1.40当量)在DMF(4ml)中的溶液中。将所得混合物缓慢加温至室温并搅拌过夜。然后将该混合物缓慢地倒入饱和水性氯化铵溶液中,并将水相用乙酸乙酯进行萃取。将有机相用水、然后用盐水来洗涤四次,经硫酸钠干燥,过滤并进行浓缩。将粗物质通过硅胶柱层析、用环己烷中的乙酸乙酯洗脱来进行纯化,以产生呈白色固体的标题化合物。LCMS(方法1):424(M+H)+;保留时间:1.32min。
2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]丙腈(化合物P6)的制备的替代性程序:
向2-氰基-2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]丙酸乙酯(化合物P9)(250mg,0.505mmol,1.00当量)在DMSO(2.0mL)的溶液中添加到在水(1.0mL)中的氯化钠(298mg,5.05mmoL,10.0当量)中,并将获得的反应混合物加热至120℃,持续2h。在冷却至室温后,将反应混合物用水(10mL)进行稀释,并且用乙酸乙酯(3×20mL)萃取。将合并的有机层干燥(Na2SO4)、过滤并且在真空中浓缩以给出粗产物。通过快速层析纯化(SiO2,30%乙酸乙酯/环己烷)提供所希望的产物。LCMS(方法4):424(M+H)+;保留时间:0.91min。
实例P9:2-氰基-2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡
啶-2-基]-3-吡啶基]丙酸乙酯(化合物P9)的制备
步骤1:2-氰基-2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]乙酸乙酯(化合物P25)的制备:
向2-(5-溴-3-乙基磺酰基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(根据WO 16096584制备)(5.40g,11.1mmol,1.00当量)在DMSO(50mL)中的溶液中添加2-氰基乙酸乙酯(3.85g,33.3mmol,3.00当量),随后添加碳酸钾(3.89g,27.8mmol,2.50当量)、L-脯氨酸(261mg,2.23mmol,0.200当量)和碘化铜(I)(212mg,1.11mmol,0.100当量)。将反应混合物加热至150℃持续3.5h。在冷却至室温后,将反应混合物用2N HCl溶液(50mL)酸化、用乙酸乙酯(3×100mL)萃取,并将合并的有机层用盐水洗涤、干燥(硫酸钠)、过滤并在减压下收缩以获得所希望的产物。LCMS(方法4):482(M+H)+;保留时间:0.95min。
步骤2:2-氰基-2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]丙酸乙酯(化合物P9)的制备
向2-氰基-2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]乙酸乙酯(500mg,1.04mmol,1.00当量)在DMF(6.0mL)中的溶液中添加碳酸钾(175mg,1.25mmol,1.20当量)和碘甲烷(78μL,180mg,1.25mmol,1.20当量)。将获得的反应混合物在室温下搅拌过夜。随后,将反应混合物用水(30mL)稀释,用乙酸乙酯(3×30mL)萃取,并将合并的有机层经硫酸钠干燥、过滤并在减压下收缩。将粗产物通过快速层析(30%乙酸乙酯/环己烷)纯化,以给出标题化合物。LCMS(方法4):496(M+H)+;保留时间:1.00min。
实例P11:2-[3-乙基硫烷基-4-[7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪-6-基]
苯基]-2-甲基-丙腈(化合物P11)的制备
步骤1:4-溴-2-乙基硫烷基-N-[3-(甲基氨基)-6-(三氟甲基)哒嗪-4-基]苯甲酰胺的制备
向N-3-甲基-6-(三氟甲基)哒嗪-3,4-二胺(800mg,4.16mmol,1.00当量)在四氢呋喃(15mL)中的溶液中添加N,N-二异丙基乙基胺(1.07mL,807mg,6.25mmol,1.50当量)。将反应混合物冷却至0℃,并逐滴添加4-溴-2-乙基硫烷基-苯甲酰氯(根据WO 2016/026848制备)(1.28g,4.58mmol,1.10当量)在四氢呋喃(15mL)中的溶液中。允许反应混合物加温至室温并搅拌过夜。通过添加饱和水性氯化铵溶液来缓慢地淬灭反应,并将水相用乙酸乙酯萃取三次。将合并的有机相用水、盐水洗涤,经硫酸钠进行干燥,过滤并进行浓缩。将粗产物通过快速层析(SiO2,乙酸乙酯/环己烷)纯化,以给出标题化合物。LCMS(方法1):435(M+H)+;保留时间:1.05min。
步骤2:6-(4-溴-2-乙基硫烷基-苯基)-7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪的制备
向配备有回流冷凝器和搅拌棒的圆底烧瓶中加入4-溴-2-乙基硫烷基-N-[3-(甲基氨基)-6-(三氟甲基)哒嗪-4-基]苯甲酰胺(4.40g,10.1mmol,1.00当量)在冰醋酸(30mL)中的溶液,并将反应混合物加热至100℃持续5h。在冷却至室温后,将反应混合物在真空中浓缩并通过与甲苯进行重复共沸蒸馏来除去剩余的乙酸。将获得的粗产物通过快速层析(SiO2,乙酸乙酯/环己烷)纯化,以提供标题化合物。LCMS(方法1):417(M+H)+;保留时间:1.09min。
步骤3:2-[3-乙基硫烷基-4-[7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪-6-基]苯基]乙腈的制备
在氩气氛下,向配备有搅拌棒和回流冷凝器的三颈烧瓶中加入6-(4-溴-2-乙基硫烷基-苯基)-7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪(1.30g,3.12mmol,1.00当量)在N,N-二甲基乙酰胺(16mL)中的溶液。向此溶液添加三甲基甲硅烷基-乙腈(1.32mL,9.35mmol,3.00当量)、氟化锌(193mg,1.87mmol,0.60当量)、xantphos(73.6mg,0.125mmol,0.0400当量)和Pd2(dba)3(44.6mg,0.046mmol,0.015当量)。将反应混合物加热至100℃持续7h。在冷却至室温后,将反应混合物用乙酸乙酯稀释,通过硅藻土塞过滤,并用水洗涤三次、用盐水洗涤一次。将有机层经硫酸钠干燥、过滤并进行浓缩。将粗物质通过快速柱层析(SiO2,乙酸乙酯/环己烷)纯化,以提供标题化合物。LCMS(方法1):378(M+H)+;保留时间:0.96min。
步骤4:2-[3-乙基硫烷基-4-[7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪-6-基]苯基]-2-甲基-丙腈(化合物P11)的制备
在氩气氛下,将2-[3-乙基硫烷基-4-[7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪-6-基]苯基]乙腈(192mg,0.509mmol,1.00当量)在N,N-二甲基甲酰胺(4mL)中的溶液冷却至0℃。在此温度下,分部分地添加氢化钠(60wt-%,在矿物油中,273mg,0.712mmol,1.40当量)。将深红色反应混合物在0℃下搅拌30min。在氩气下,0℃下,将获得的混合物经由注射器添加到甲基碘(44μl,101mg,0.712mmol,1.40当量)在DMF(4mL)中的溶液中。将所得混合物缓慢加温至室温并搅拌过夜。然后将该混合物缓慢地倒入饱和水性氯化铵溶液中,并将水相用乙酸乙酯进行萃取。将有机相用水、然后用盐水来洗涤四次,经硫酸钠干燥,过滤并进行浓缩。将粗物质通过硅胶柱层析、用环己烷中的乙酸乙酯洗脱来进行纯化,以产生标题化合物。LCMS(方法1):406(M+H)+;保留时间:1.03min。
实例P12:2-[3-乙基磺酰基-4-[7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪-6-基]
苯基]-2-甲基-丙腈(化合物P12)的制备
在室温下,向2-[3-乙基硫烷基-4-[7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪-6-基]苯基]-2-甲基-丙腈(化合物P11)(74.0mg,0.183mmol,1.00当量)在二氯甲烷(2.0mL)中的溶液中添加3-氯过苯甲酸(75wt-%,92.4mg,0.384mmol,2.10当量)。在室温下继续搅拌18h,然后添加饱和硫代硫酸钠(10mL)和饱和NaHCO3(10mL)溶液。将反应混合物用二氯甲烷(50mL)稀释,并将混合物搅拌20min。将水层分离后,用二氯甲烷(3×20mL)萃取,将合并的有机层用水和盐水洗涤、干燥(Na2SO4)并在减压下浓缩。将获得的粗物质通过快速层析纯化(SiO2,乙酸乙酯/环己烷),以提供标题化合物。LCMS(方法1):438(M+H)+;保留时间:0.93min。
实例P15:2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-
基]-3-吡啶基]-2,2-二氟-乙腈(化合物P15)的制备
在氮气下,向2-[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]乙腈(参见实例P3,步骤1)(409mg,1.00mmol,1.00当量)在四氢呋喃(6.0mL)中的溶液中添加Cs2CO3(391mg,1.20mmol,1.00当量),随后添加N-氟代苯磺酰亚胺(315mg,1.00mmol,1.00当量)。将反应混合物在室温下搅拌,持续1小时。将获得的反应混合物用乙酸乙酯(30mL)和水(30mL)稀释。用乙酸乙酯(3×30mL)萃取后,将合并的有机层用水(2×30mL)洗涤并用硫酸钠干燥。在减压下浓缩并且通过快速层析纯化(SiO2,乙酸乙酯/环己烷)提供呈白色固体的标题化合物。LCMS(方法4):446(M+H)+;保留时间:1.05min。
实例P16:2-[3-乙基硫烷基-4-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]
苯基]-2-甲基-丙腈(化合物P16)的制备
向微波小瓶中加入2-(4-溴-2-乙基硫烷基-苯基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(根据WO 2016/026848制备)(500mg,1.20mmol,1.00当量)、外消旋-BINAP(77.1mg,.0120mmol,0.10当量)、和Pd2(dba)3(56.7mg,0.0600mmol,0.0500当量)。用氩气冲洗之后,添加四氢呋喃(THF)(1.20mL)和环戊基甲基醚(CPME)(1.20mL),随后添加异丁腈(119μL,91.7mg,1.32mmol,1.10当量)。在氩气氛下将小瓶加盖,并将获得的溶液冷却至-25℃。在搅拌25min后,经5min逐滴添加LiHMDS(THF中的1M溶液,1.32mL,1.32mmol,1.10当量)。允许获得的溶液加温至室温,然后加热至80℃,持续4h。在冷却至室温之后,将反应混合物用水淬灭,通过硅藻土塞过滤,并用乙酸乙酯冲洗。将水层用乙酸乙酯(3x)萃取,并将合并的有机相用水和盐水洗涤。经硫酸钠干燥、过滤并在真空中浓缩来提供粗物质,将该粗物质通过快速层析纯化(SiO2,乙酸乙酯/环己烷),以提供标题化合物。LCMS(方法1):405(M+H)+;保留时间:1.02min。
实例P17:2-[3-乙基磺酰基-4-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]
苯基]-2-甲基-丙腈(化合物P17)的制备
在室温下,向2-[3-乙基硫烷基-4-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]苯基]-2-甲基-丙腈(化合物P16)(88.8mg,0.220mmol,1.00当量)在二氯甲烷(1.0mL)中的溶液中添加3-氯过苯甲酸(75wt-%,103mg,0.461mmol,2.10当量)。在室温下继续搅拌18h,然后添加饱和硫代硫酸钠(5mL)和饱和NaHCO3(5mL)溶液。将反应混合物用二氯甲烷(15mL)稀释,并将混合物搅拌20min。将水层分离后,用二氯甲烷(3×10mL)萃取,将合并的有机层用水和盐水洗涤、干燥(Na2SO4)并在减压下浓缩。将获得的粗物质通过快速层析纯化(SiO2,MeOH/二氯甲烷),以提供标题化合物。LCMS(方法1):437(M+H)+;保留时间:0.90min。
实例P19:2-[6-(6-溴-3-甲基-咪唑并[4,5-c]吡啶-2-基)-5-乙基磺酰基-3-吡啶
基]-2-甲基-丙腈(化合物P19)的制备
步骤1:5-(1-氰基-2-乙氧基-2-氧代-乙基)-3-乙基硫烷基-吡啶-2-甲酸甲基酯的制备
向5-溴-3-乙基硫烷基-吡啶-2-甲酸甲基酯(根据WO 2017/055147制备)(32.0g,116mmol,1.00当量)在DMSO(350mL)中的溶液中添加2-氰基乙酸乙酯(18.5mL,19.7g,174mmol,1.50当量)、K2CO3(40.4g,290mmol,2.50当量)和四丁基溴化铵(3.81g,11.6mmol,0.100当量)。将所得悬浮液加热至90℃过夜。在冷却至室温后,将反应混合物用水(150mL)和乙酸乙酯(300mL)进行稀释,并冷却至0℃。向搅拌的混合物中缓慢地添加2M HCl(200mL)(放热反应)直到达到pH 4-5。将水层分离并用乙酸乙酯(3×500mL)萃取。将合并的有机层经硫酸钠干燥并在真空中浓缩,以获得粗物质。从乙醇重结晶,提供呈黄褐色固体的标题化合物。LCMS(方法1):309(M+H)+;保留时间:0.86min。
步骤2:5-(氰基甲基)-3-乙基硫烷基-吡啶-2-甲酸甲基酯的制备
在配备有磁力搅拌棒和回流冷凝器和排气的三颈烧瓶中,向5-(1-氰基-2-乙氧基-2-氧代-乙基)-3-乙基硫烷基-吡啶-2-甲酸甲基酯(21.1g,68.4mmol,1.00当量)在DMSO(210mL)的溶液中首先添加氯化钠(40.0g,684mmol,10.0当量),随后添加水(105mL)。将反应混合物加热至内部温度为125℃,在此温度下进行强气体。继续搅拌3h。在冷却至室温后,将反应混合物用水(50mL)进行稀释,并添加乙酸乙酯(100mL)。将水层分离后,用乙酸乙酯(3×200mL)萃取,并将合并的有机层用水洗涤、干燥(Na2SO4)并在真空中浓缩,以给出粗物质。将粗产物如所获得的那样直接使用。LCMS(方法1):237(M+H)+;保留时间:0.72min
步骤3:5-(1-氰基-1-甲基-乙基)-3-乙基硫烷基-吡啶-2-甲酸的制备
向5-(氰基甲基)-3-乙基硫烷基-吡啶-2-甲酸甲基酯(20.0g,84.6mmol,1.00当量)在1,4-二噁烷(170mL)中的溶液中添加苄基三甲基铵氯化物(998mg,4.23mmol,0.0500当量),并将获得的溶液冷却至0℃.向这个溶液中缓慢地添加水性NaOH(30wt%,59mL,590mmol,7.0当量),随后逐滴添加碘甲烷(10.5mL,24.0g,169mmol,2.00当量),同时保持温度在0至5℃之间。继续在0℃下搅拌5h,然后通过缓慢添加2M HCl直到达到pH 5来淬灭反应混合物。添加乙酸乙酯(250mL)并搅拌30min后,将各层分离并将水层用乙酸乙酯(3×100mL)萃取。将合并的有机层用水(50mL)和盐水(50mL)洗涤,干燥(Na2SO4),并蒸发。将粗物质通过快速层析纯化(SiO2,乙酸乙酯/环己烷),以提供标题化合物。LCMS(方法1):251(M+H)+;保留时间:0.71min。
步骤4:N-[2-溴-5-(甲基氨基)-4-吡啶基]-5-(1-氰基-1-甲基-乙基)-3-乙基硫烷基-吡啶-2-甲酰胺的制备
在氩气下,经由注射器,向5-(1-氰基-1-甲基-乙基)-3-乙基硫烷基-吡啶-2-甲酸(10.0g,40.0mmol,1.00当量)和催化量的N,N-二甲基甲酰胺在二氯甲烷(24mL)中的溶液中逐滴添加草酰氯(5.23mL,7.61g,59.9mmol,1.50当量)。然后将反应混合物加热至回流3h。冷却至室温后,将反应混合物蒸发至干。将所得棕色油溶解在THF(190mL)中,并在0℃下经由滴液漏斗缓慢地添加到6-溴-N3-甲基-吡啶-3,4-二胺(根据WO 2016/107831制备)(8.43g,41.7mmol,1.04当量)和N,N-二异丙基乙基胺(16.7mL,12.4g,94.9mmol,2.54当量)在THF(300mL)中的溶液中。允许反应加温至室温并继续搅拌20h。通过添加饱和水性氯化铵溶液来缓慢地淬灭反应,并将水相用乙酸乙酯进行萃取。将合并的有机相用水、盐水洗涤,经硫酸钠干燥,过滤并进行浓缩,以提供呈粗物质的标题化合物。LCMS(方法1):434(M+H)+;保留时间:0.82min。
步骤5:2-[6-(6-溴-3-甲基-咪唑并[4,5-c]吡啶-2-基)-5-乙基硫烷基-3-吡啶基]-2-甲基-丙腈(化合物P23)的制备
向配备有回流冷凝器和搅拌棒的圆底烧瓶中加入在冰醋酸(90mL)中的N-[2-溴-5-(甲基氨基)-4-吡啶基]-5-(1-氰基-1-甲基-乙基)-3-乙基硫烷基-吡啶-2-甲酰胺(13.0g,29.9mmol,1.00当量)溶液,并将反应混合物加热至100℃,持续5h。在冷却至室温后,将反应混合物在真空中浓缩并通过与甲苯进行重复共沸蒸馏来除去剩余的乙酸。将获得的粗产物通过快速层析(SiO2,乙酸乙酯/环己烷)纯化,以提供标题化合物。LCMS(方法1):416(M+H)+;保留时间:0.94min。
步骤6:2-[6-(6-溴-3-甲基-咪唑并[4,5-c]吡啶-2-基)-5-乙基磺酰基-3-吡啶基]-2-甲基-丙腈(化合物P19)的制备
在0℃下,向2-[6-(6-溴-3-甲基-咪唑并[4,5-c]吡啶-2-基)-5-乙基硫烷基-3-吡啶基]-2-甲基-丙腈(化合物P23)(7.10g,17.1mmol,1.00当量)在二氯甲烷(171mL)中的溶液中以小部分添加3-氯过苯甲酸(75wt-%,8.04g,35.0mmol,2.05当量)(放热反应)。允许反应混合物加温至室温,并在室温下继续搅拌18h,然后添加饱和硫代硫酸钠溶液(100mL)和饱和NaHCO3(100mL)。将反应混合物用二氯甲烷(150mL)稀释,并将混合物搅拌20min。分离水层后,用二氯甲烷(3×10mL)进行萃取,用饱和硫代硫酸钠(50mL),饱和NaHCO3(50mL),随后用水(50mL)和盐水(50mL)洗涤合并的有机层。将Na2SO4干燥,并且在减压下浓缩,产生了粗材料,将该粗材料通过快速层析进行纯化(SiO2,MeOH/二氯甲烷)以提供标题化合物。LCMS(方法1):448(M+H)+;保留时间:0.88min。
实例P20:2-[5-乙基磺酰基-6-[3-甲基-6-(1,1,2,2,2-五氟乙基)咪唑并[4,5-c]
吡啶-2-基]-3-吡啶基]-2-甲基-丙腈(化合物P20)的制备
步骤1:2-[5-乙基磺酰基-6-(6-碘-3-甲基-咪唑并[4,5-c]吡啶-2-基)-3-吡啶基]-2-甲基-丙腈(化合物P22)的制备
向2-[6-(6-溴-3-甲基-咪唑并[4,5-c]吡啶-2-基)-5-乙基磺酰基-3-吡啶基]-2-甲基-丙腈(化合物P19)(1.00g,2.23mmol,1.00当量)在1,4-二噁烷(11mL)中的溶液中添加NaI(689mg,4.46mmol,2.00当量)、CuI(224mg,1.12mmol,0500当量)和N,N’-二甲基乙二胺(DMEDA)(0.29mL,0.24g,2.7mmol,1.2当量)。将反应混合物加热至100℃持续40h。在冷却至室温之后,将反应混合物用乙酸乙酯(50mL)稀释并添加1M NH3水溶液。将水层分离并用乙酸乙酯(2×20mL)萃取。将合并的有机层用饱和NaHCO3、水和盐水洗涤,并干燥(Na2SO4)。在减压下浓缩,提供标题化合物。LCMS(方法1):496(M+H)+;保留时间:0.90min。
步骤2:2-[5-乙基磺酰基-6-[3-甲基-6-(1,1,2,2,2-五氟乙基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]-2-甲基-丙腈(化合物P20)的制备
在氩气氛下,向2-[5-乙基磺酰基-6-(6-碘-3-甲基-咪唑并[4,5-c]吡啶-2-基)-3-吡啶基]-2-甲基-丙腈(化合物P22)(900mg,1.82mmol,1.00当量)在DMF(6.5mL)中的溶液中添加(phen)CuC2F5[1360806-59-2]。将搅拌的反应混合物加热至90℃持续2h。在冷却至室温之后,将反应混合物用硅藻土过滤并用乙酸乙酯冲洗。将滤液用28%氨水(20mL)、NaHCO3(20mL)、水(20mL)和盐水(20mL)洗涤。经硫酸钠干燥、过滤并在减压下浓缩来提供粗产物。通过快速层析纯化(SiO2,乙酸乙酯/环己烷)产生呈白色固体的标题化合物。LCMS(方法1):488(M+H)+;保留时间:1.00min。
实例P23:2-[5-乙基硫烷基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-
基]-3-吡啶基]-2-甲基-丙腈(化合物P23)的制备
向配备有滴液漏斗和氩气入口的三颈烧瓶中加入异丁腈(4.30mL,3.31g,47.9mmol,2.00当量)并冷却至-25℃。在该温度下,在30min内逐滴添加LiHMDS(在THF中的1.0M溶液,72mL,64g,72mmol,3.0当量),同时将搅拌的反应混合物保持在-25℃。在此温度下继续搅拌15min。然后在-25℃下经1.5h的时间,将获得的溶液逐滴添加到2-(5-溴-3-乙基硫烷基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(根据WO 2016/026848制备)(10.0g,24.0mmol,1.00当量)在THF(50mL)中的搅拌的溶液中。在此温度下继续搅拌30min,然后允许加温至室温。在此温度下再过1h后,通过缓慢地添加水(50mL)和乙酸乙酯(100mL)来淬灭反应混合物。将水层分离并用乙酸乙酯(2×50mL)萃取,并且将合并的有机层用盐水洗涤并经硫酸钠干燥。在真空中浓缩并通过快速层析进行纯化,提供所希望的标题化合物。LCMS(方法1):406(M+H)+;保留时间:0.99min。
表4:具有式(I)的化合物的实例
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表I1:具有式(XVI)、(XIV)、(XII)、(XI)、(XIII)、(IX)、和(II)的新颖中间体化合
物的实例:
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以下具有式I的化合物与活性成分的混合物是优选的(缩写“TX”意为“选自下组的一种化合物,该组由描述于本发明的表1-4中的化合物组成”):
佐剂,该佐剂选自由以下物质组成的组:石油(别名)(628)+TX,
杀螨剂,该杀螨剂选自由以下项组成的物质组:1,1-双(4-氯苯基)-2-乙氧基乙醇(IUPAC名称)(910)+TX、2,4-二氯苯基苯磺酸酯(IUPAC/化学文摘名)(1059)+TX、2-氟-N-甲基-N-1-萘乙酰胺(IUPAC名称)(1295)+TX、4-氯苯基苯基砜(IUPAC名称)(981)+TX、阿维菌素(1)+TX、灭螨醌(3)+TX、乙酰虫腈[CCN]+TX、氟丙菊酯(9)+TX、涕灭威(16)+TX、涕灭砜威(863)+TX、α-氯氰菊酯(202)+TX、赛硫磷(870)+TX、磺胺螨酯[CCN]+TX、果满磷(amidothioate)(872)+TX、胺吸磷(875)+TX、胺吸磷草酸氢盐(875)+TX、双甲脒(24)+TX、杀螨特(881)+TX、三氧化二砷(882)+TX、AVI 382(化合物代码)+TX、AZ 60541(化合物代码)+TX、益棉磷(44)+TX、保棉磷(azinphos-methyl)(45)+TX、偶氮苯(IUPAC名称)(888)+TX、三唑锡(azacyclotin)(46)+TX、偶氮磷(azothoate)(889)+TX、苯菌灵(62)+TX、苯诺沙磷(benoxafos)(别名)[CCN]+TX、苯螨特(benzoximate)(71)+TX、苯甲酸苄酯(IUPAC名称)[CCN]+TX、联苯肼酯(74)+TX、联苯菊酯(76)+TX、乐杀螨(907)+TX、溴灭菊酯(brofenvalerate)(别名)+TX、溴烯杀(bromocyclen)(918)+TX、溴硫磷(920)+TX、乙基溴硫磷(921)+TX、溴螨酯(bromopropylate)(94)+TX、噻嗪酮(99)+TX、丁酮威(103)+TX、丁酮砜威(104)+TX、丁基哒螨灵(别名)+TX、多硫化钙(IUPAC名称)(111)+TX、毒杀芬(campheechlor)(941)+TX、氯灭杀威(carbanolate)(943)+TX、甲萘威(115)+TX、克百威(carbofuran)(118)+TX、卡波硫磷(947)+TX、CGA 50’439(开发代码)(125)+TX、灭螨猛(chinomethionat)(126)+TX、杀螨醚(chlorbenside)(959)+TX、杀虫脒(964)+TX、杀虫脒盐酸盐(964)+TX、溴虫腈(130)+TX、敌螨(968)+TX、杀螨酯(chlorfenson)(970)+TX、敌螨特(chlorfensulfide)(971)+TX、氯芬磷(131)+TX、乙酯杀螨醇(chlorobenzilate)(975)+TX、伊托明(chloromebuform)(977)+TX、灭虫脲(chloromethiuron)(978)+TX、丙酯杀螨醇(chloropropylate)(983)+TX、毒死蜱(145)+TX、甲基毒死蜱(146)+TX、虫螨磷(chlorthiophos)(994)+TX、瓜菊酯(cinerin)I(696)+TX、瓜菊酯II(696)+TX、瓜叶除虫菊酯(cinerins)(696)+TX、四螨嗪(158)+TX、氯氰碘柳胺(别名)[CCN]+TX、库马磷(174)+TX、克罗米通(别名)[CCN]+TX、巴毒磷(crotoxyphos)(1010)+TX、硫杂灵(1013)+TX、果虫磷(cyanthoate)(1020)+TX、丁氟螨酯(CAS登记号:400882-07-7)+TX、三氯氟氰菊酯(196)+TX、三环锡(199)+TX、氯氰菊酯(201)+TX、DCPM(1032)+TX、DDT(219)+TX、田乐磷(demephion)(1037)+TX、田乐磷-O(1037)+TX、田乐磷-S(1037)+TX、内吸磷(demeton)(1038)+TX、甲基内吸磷(224)+TX、内吸磷-O(1038)+TX、甲基内吸磷-O(demeton-O-methyl)(224)+TX、内吸磷-S(1038)+TX、甲基内吸磷-S(224)+TX、内吸磷-S-甲基磺隆(demeton-S-methylsulfon)(1039)+TX、杀螨隆(226)+TX、氯亚胺硫磷(dialifos)(1042)+TX、二嗪磷(227)+TX、苯氟磺胺(230)+TX、敌敌畏(236)+TX、甲氟磷(dicliphos)(别名)+TX、开乐散(242)+TX、百治磷(243)+TX、遍地克(1071)+TX、甲氟磷(dimefox)(1081)+TX、乐果(262)+TX、二甲杀螨霉素(dinactin)(别名)(653)+TX、消螨酚(dinex)(1089)+TX、消螨酚(dinex-diclexine)(1089)+TX、消螨通(dinobuton)(269)+TX、敌螨普(dinocap)(270)+TX、敌螨普-4[CCN]+TX、敌螨普-6[CCN]+TX、敌螨消(dinocton)(1090)+TX、硝戊酯(dinopenton)(1092)+TX、硝辛酯(dinosulfon)(1097)+TX、硝丁酯(dinoterbon)(1098)+TX、敌恶磷(1102)+TX、二苯砜(IUPAC名称)(1103)+TX、双硫仑(别名)[CCN]+TX、乙拌磷(278)+TX、DNOC(282)+TX、苯氧炔螨(dofenapyn)(1113)+TX、多拉菌素(别名)[CCN]+TX、硫丹(294)+TX、因毒磷(endothion)(1121)+TX、EPN(297)+TX、依立诺克丁(别名)[CCN]+TX、乙硫磷(309)+TX、益硫磷(ethoate-methyl)(1134)+TX、乙螨唑(etoxazole)(320)+TX、乙嘧硫磷(etrimfos)(1142)+TX、抗螨唑(fenazaflor)(1147)+TX、喹螨醚(328)+TX、苯丁锡(fenbutatin oxide)(330)+TX、苯硫威(fenothiocarb)(337)+TX、甲氰菊酯(342)+TX、吡螨胺(fenpyrad)(别名)+TX、唑螨酯(fenpyroximate)(345)+TX、芬螨酯(fenson)(1157)+TX、氟硝二苯胺(fentrifanil)(1161)+TX、氰戊菊酯(349)+TX、氟虫腈(354)+TX、嘧螨酯(fluacrypyrim)(360)+TX、氟佐隆(1166)+TX、氟螨噻(flubenzimine)(1167)+TX、氟螨脲(366)+TX、氟氰戊菊酯(flucythrinate)(367)+TX、联氟螨(fluenetil)(1169)+TX、氟虫脲(370)+TX、氟氯苯菊酯(flumethrin)(372)+TX、氟杀螨(fluorbenside)(1174)+TX、氟胺氰菊酯(fluvalinate)(1184)+TX、FMC 1137(开发代码)(1185)+TX、抗螨脒(405)+TX、抗螨脒盐酸盐(405)+TX、安硫磷(formothion)(1192)+TX、胺甲威(formparanate)(1193)+TX、γ-HCH(430)+TX、果绿啶(glyodin)(1205)+TX、苄螨醚(halfenprox)(424)+TX、庚烯磷(heptenophos)(432)+TX、十六碳烷基环丙烷羧酸酯(IUPAC/化学文摘名)(1216)+TX、噻螨酮(441)+TX、碘甲烷(IUPAC名称)(542)+TX、水胺硫磷(isocarbophos)(别名)(473)+TX、异丙基0-(甲氧基氨基硫代磷酰基)水杨酸酯(IUPAC名称)(473)+TX、伊维菌素(别名)[CCN]+TX、茉莉菊酯(jasmolin)I(696)+TX、茉莉菊酯II(696)+TX、碘硫磷(jodfenphos)(1248)+TX、林丹(430)+TX、虱螨脲(490)+TX、马拉硫磷(492)+TX、丙螨氰(malonoben)(1254)+TX、灭蚜磷(mecarbam)(502)+TX、地胺磷(mephosfolan)(1261)+TX、甲硫芬(别名)[CCN]+TX、虫螨畏(methacrifos)(1266)+TX、甲胺磷(527)+TX、杀扑磷(529)+TX、灭虫威(530)+TX、灭多虫(531)+TX、溴甲烷(537)+TX、速灭威(metolcarb)(550)+TX、速灭磷(556)+TX、自克威(mexacarbate)(1290)+TX、弥拜菌素(milbemectin)(557)+TX、杀螨菌素肟(milbemycinoxime)(别名)[CCN]+TX、丙胺氟磷(mipafox)(1293)+TX、久效磷(561)+TX、茂硫磷(morphothion)(1300)+TX、莫昔克丁(别名)[CCN]+TX、二溴磷(naled)(567)+TX、NC-184(化合物代码)+TX、NC-512(化合物代码)+TX、氟蚊灵(nifluridide)(1309)+TX、尼柯霉素(别名)[CCN]+TX、戊氰威(nitrilacarb)(1313)+TX、戊氰威(nitrilacarb)1:1氯化锌络合物(1313)+TX、NNI-0101(化合物代码)+TX、NNI-0250(化合物代码)+TX、氧乐果(594)+TX、杀线威(602)+TX、亚异砜磷(oxydeprofos)(1324)+TX、砜拌磷(oxydisulfoton)(1325)+TX、pp’-DDT(219)+TX、对硫磷(615)+TX、氯菊酯(626)+TX、石油(别名)(628)+TX、芬硫磷(1330)+TX、稻丰散(631)+TX、甲拌磷(636)+TX、伏杀硫磷(637)+TX、硫环磷(phosfolan)(1338)+TX、亚胺硫磷(638)+TX、磷胺(639)+TX、辛硫磷(642)+TX、甲基嘧啶磷(652)+TX、氯化松节油(polychloroterpenes)(传统名称)(1347)+TX、杀螨霉素(polynactins)(别名)(653)+TX、丙氯诺(1350)+TX、丙溴磷(662)+TX、蜱虱威(promacyl)(1354)+TX、克螨特(671)+TX、胺丙畏(propetamphos)(673)+TX、残杀威(678)+TX、乙噻唑磷(prothidathion)(1360)+TX、发硫磷(prothoate)(1362)+TX、除虫菊酯I(696)+TX、除虫菊酯II(696)+TX、除虫菊素(pyrethrins)(696)+TX、哒螨灵(699)+TX、哒嗪硫磷(pyridaphenthion)(701)+TX、嘧螨醚(pyrimidifen)(706)+TX、嘧硫磷(1370)+TX、喹硫磷(quinalphos)(711)+TX、喹硫磷(quintiofos)(1381)+TX、R-1492(开发代码)(1382)+TX、RA-17(开发代码)(1383)+TX、鱼藤酮(722)+TX、八甲磷(schradan)(1389)+TX、克线丹(sebufos)(别名)+TX、塞拉菌素(selamectin)(别名)[CCN]+TX、SI-0009(化合物代码)+TX、苏硫磷(sophamide)(1402)+TX、季酮螨酯(738)+TX、螺甲螨酯(739)+TX、SSI-121(开发代码)(1404)+TX、舒非仑(别名)[CCN]+TX、氟虫胺(sulfluramid)(750)+TX、治螟磷(sulfotep)(753)+TX、硫磺(754)+TX、SZI-121(开发代码)(757)+TX、氟胺氰菊酯(tau-fluvalinate)(398)+TX、吡螨胺(763)+TX、TEPP(1417)+TX、叔丁威(terbam)(别名)+TX、司替罗磷(777)+TX、三氯杀螨砜(tetradifon)(786)+TX、杀螨霉素(tetranactin)(别名)(653)+TX、杀螨硫醚(tetrasul)(1425)+TX、thiafenox(别名)+TX、抗虫威(thiocarboxime)(1431)+TX、久效威(thiofanox)(800)+TX、甲基乙拌磷(thiometon)(801)+TX、克杀螨(1436)+TX、苏云金素(thuringiensin)(别名)[CCN]+TX、威菌磷(triamiphos)(1441)+TX、苯螨噻(triarathene)(1443)+TX、三唑磷(820)(别名)+TX、唑呀威(triazuron)+TX、敌百虫(824)+TX、三氯丙氧磷(trifenofos)(1455)+TX、三活菌素(trinactin)(别名)(653)+TX、蚜灭多(847)+TX、氟吡唑虫(vaniliprole)[CCN]和YI-5302(化合物代码)+TX,
杀藻剂,该杀藻剂选自由以下物质组成的组:3-苯并[b]噻吩-2-基-5,6-二氢-1,4,2-噁噻嗪-4-氧化物[CCN]+TX、二辛酸铜(IUPAC名称)(170)+TX、硫酸铜(172)+TX、cybutryne[CCN]+TX、二氢萘醌(dichlone)(1052)+TX、双氯酚(232)+TX、菌多酸(295)+TX、三苯锡(fentin)(347)+TX、熟石灰[CCN]+TX、代森钠(nabam)(566)+TX、灭藻醌(quinoclamine)(714)+TX、醌萍胺(quinonamid)(1379)+TX、西玛津(730)+TX、三苯锡乙酸盐(IUPAC名称)(347)和氢氧化三苯锡(IUPAC名称)(347)+TX,
驱蠕虫剂,该驱蠕虫剂选自由以下物质组成的组:阿巴美丁(1)+TX、克芦磷酯(1011)+TX、多拉克汀(别名)[CCN]+TX、依马克丁(291)+TX、依马克丁苯甲酸酯(291)+TX、依立诺克丁(别名)[CCN]+TX、伊维菌素(别名)[CCN]+TX、米尔倍霉素(别名)[CCN]+TX、莫昔克丁(别名)[CCN]+TX、哌嗪[CCN]+TX、塞拉菌素(selamectin)(别名)[CCN]+TX、多杀菌素(737)和硫菌灵(thiophanate)(1435)+TX,
杀鸟剂,该杀鸟剂选自由以下物质组成的组:氯醛糖(127)+TX、异狄氏剂(1122)+TX、倍硫磷(346)+TX、吡啶-4-胺(IUPAC名称)(23)和士的宁(745)+TX,
杀细菌剂,该杀细菌剂选自由以下物质组成的组:1-羟基-1H-吡啶-2-硫酮(IUPAC名称)(1222)+TX、4-(喹喔啉-2-基氨基)苯磺酰胺(IUPAC名称)(748)+TX、8-羟基喹啉硫酸盐(446)+TX、溴硝醇(97)+TX、二辛酸铜(IUPAC名称)(170)+TX、氢氧化铜(IUPAC名称)(169)+TX、甲酚[CCN]+TX、双氯酚(232)+TX、双吡硫翁(1105)+TX、多地辛(1112)+TX、敌磺钠(fenaminosulf)(1144)+TX、甲醛(404)+TX、汞加芬(别名)[CCN]+TX、春雷霉素(483)+TX、春雷霉素盐酸盐水合物(483)+TX、二(二甲基二硫代氨基甲酸盐)镍(IUPAC名称)(1308)+TX、三氯甲基吡啶(nitrapyrin)(580)+TX、辛噻酮(octhilinone)(590)+TX、奥索利酸(606)+TX、土霉素(611)+TX、羟基喹啉硫酸钾(446)+TX、烯丙苯噻唑(probenazole)(658)+TX、链霉素(744)+TX、链霉素倍半硫酸盐(744)+TX、叶枯酞(766)+TX、和硫柳汞(别名)[CCN]+TX,
生物试剂,该生物试剂选自由以下物质构成的组:棉褐带卷蛾颗粒体病毒(Adoxophyes orana GV)(别名)(12)+TX、放射形土壤杆菌(别名)(13)+TX、捕食螨(别名)(19)+TX、芹菜夜蛾核多角体病毒(Anagrapha falcifera NPV)(别名)(28)+TX、Anagrusatomus(别名)(29)+TX、蚜虫寄生蜂(别名)(33)+TX、棉蚜寄生蜂(别名)(34)+TX、食蚜瘿蚊(别名)(35)+TX、苜蓿银纹夜蛾核多角体病毒(Autographa californica NPV)(别名)(38)+TX、坚强芽孢杆菌(别名)(48)+TX、球形芽孢杆菌(学名)(49)+TX、苏云金杆菌(Bacillusthuringiensis Berliner)(学名)(51)+TX、苏云金杆菌鲇泽亚种(Bacillusthuringiensis subsp.aizawai)(学名)(51)+TX、苏云金杆菌以色列亚种(Bacillusthuringiensis subsp.israelensis)(学名)(51)+TX、苏云金杆菌日本亚种(Bacillusthuringiensis subsp.japonensis)(学名)(51)+TX、苏云金杆菌k.(Bacillusthuringiensis subsp.kurstaki)(学名)(51)+TX、苏云金杆菌t.(Bacillusthuringiensis subsp.tenebrionis)(学名)(51)+TX、球孢白僵菌(别名)(53)+TX、布氏白僵菌(别名)(54)+TX、草蜻蛉(别名)(151)+TX、孟氏隐唇瓢虫(别名)(178)+TX、苹果蠹蛾颗粒体病毒(Cydia pomonella GV)(别名)(191)+TX、西伯利亚离颚茧蜂(别名)(212)+TX、豌豆潜叶蝇姬小蜂(别名)(254)+TX、丽蚜小蜂(学名)(293)+TX、桨角蚜小蜂(别名)(300)+TX、玉米穗夜蛾核多角体病毒(Helicoverpa zea NPV)(别名)(431)+TX、嗜菌异小杆线虫和H.megidis(别名)(433)+TX、会聚长足瓢虫(Hippodamia convergens)(别名)(442)+TX、橘粉介壳虫寄生蜂(Leptomastix dactylopii)(别名)(488)+TX、盲蝽(Macrolophuscaliginosus)(别名)(491)+TX、甘蓝夜蛾核多角体病毒(Mamestra brassicae NPV)(别名)(494)+TX、Metaphycus helvolus(别名)(522)+TX、黄绿绿僵菌(Metarhizium anisopliaevar.acridum)(学名)(523)+TX、金龟子绿僵菌小孢变种(Metarhizium anisopliaevar.anisopliae)(学名)(523)+TX、松黄叶蜂(Neodiprion sertifer)核多角体病毒和红头松树叶蜂(N.lecontei)核多角体病毒(别名)(575)+TX、小花蝽(别名)(596)+TX、玫烟色拟青霉(别名)(613)+TX、智利捕植螨(别名)(644)+TX、甜菜夜蛾(Spodoptera exiguamulticapsid)多核衣壳核多角体病毒(学名)(741)+TX、毛蚊线虫(别名)(742)+TX、小卷蛾斯氏线虫(别名)(742)+TX、夜蛾斯氏线虫(别名)(742)+TX、Steinernema glaseri(别名)(742)+TX、Steinernema riobrave(别名)(742)+TX、Steinernema riobravis(别名)(742)+TX、Steinernema scapterisci(别名)(742)+TX、斯氏线虫属(别名)(742)+TX、赤眼蜂属(别名)(826)+TX、西方盲走螨(别名)(844)和蜡蚧轮枝菌(别名)(848)+TX,
土壤消毒剂,该土壤消毒剂选自由以下物质组成的组:碘甲烷(IUPAC名称)(542)和甲基溴(537)+TX,
化学不育剂,该化学不育剂选自由以下物质组成的组:唑磷嗪(apholate)[CCN]+TX、双(氮丙啶)甲氨基膦硫化物(bisazir)(别名)[CCN]+TX、白消安(别名)[CCN]+TX、除虫脲(250)+TX、迪麦替夫(dimatif)(别名)[CCN]+TX、六甲蜜胺(hemel)[CCN]+TX、六甲磷(hempa)[CCN]+TX、甲基涕巴(metepa)[CCN]+TX、甲硫涕巴(methiotepa)[CCN]+TX、不育特(methyl apholate)[CCN]+TX、不孕啶(morzid)[CCN]+TX、氟幼脲(penfluron)(别名)[CCN]+TX、涕巴(tepa)[CCN]+TX、硫代六甲磷(thiohempa)(别名)[CCN]+TX、硫涕巴(别名)[CCN]+TX、曲他胺(别名)[CCN]和尿烷亚胺(别名)[CCN]+TX,
昆虫信息素,该昆虫信息素选自由以下物质组成的组:(E)-癸-5-烯-1-基乙酸酯与(E)-癸-5-烯-1-醇(IUPAC名称)(222)+TX、(E)-十三碳-4-烯-1-基乙酸酯(IUPAC名称)(829)+TX、(E)-6-甲基庚-2-烯-4-醇(IUPAC名称)(541)+TX、(E,Z)-十四碳-4,10-二烯-1-基乙酸酯(IUPAC名称)(779)+TX、(Z)-十二碳-7-烯-1-基乙酸酯(IUPAC名称)(285)+TX、(Z)-十六碳-11-烯醛(IUPAC名称)(436)+TX、(Z)-十六碳-11-烯-1-基乙酸酯(IUPAC名称)(437)+TX、(Z)-十六碳-13-烯-11-炔-1-基乙酸酯(IUPAC名称)(438)+TX、(Z)-二十-13-烯-10-酮(IUPAC名称)(448)+TX、(Z)-十四碳-7-烯-1-醛(IUPAC名称)(782)+TX、(Z)-十四碳-9-烯-1-醇(IUPAC名称)(783)+TX、(Z)-十四碳-9-烯-1-基乙酸酯(IUPAC名称)(784)+TX、(7E,9Z)-十二碳-7,9-二烯-1-基乙酸酯(IUPAC名称)(283)+TX、(9Z,11E)-十四碳-9,11-二烯-1-基乙酸酯(IUPAC名称)(780)+TX、(9Z,12E)-十四碳-9,12-二烯-1-基乙酸酯(IUPAC名称)(781)+TX、14-甲基十八-1-烯(IUPAC名称)(545)+TX、4-甲基壬醛-5-醇与4-甲基壬醛-5-酮(IUPAC名称)(544)+TX、α-多纹素(multistriatin)(别名)[CCN]+TX、西部松小蠹集合信息素(brevicomin)(别名)[CCN]+TX、十二碳二烯醇(codlelure)(别名)[CCN]+TX、十二碳二烯醇(codlemone)(别名)(167)+TX、诱蝇酮(cuelure)(别名)(179)+TX、环氧十九烷(disparlure)(277)+TX、十二碳-8-烯-1基乙酸酯(IUPAC名称)(286)+TX、十二碳-9-烯-1-基乙酸酯(IUPAC名称)(287)+TX、十二碳-8+TX、10-二烯-1-基乙酸酯(IUPAC名称)(284)+TX、多米尼加(dominicalure)(别名)[CCN]+TX、4-甲基辛酸乙酯(IUPAC名称)(317)+TX、丁香酚(别名)[CCN]+TX、南部松小蠹集合信息素(frontalin)(别名)[CCN]+TX、诱虫十六酯(gossyplure)(别名)(420)+TX、诱杀烯混剂(grandlure)(421)+TX、诱杀烯混剂I(别名)(421)+TX、诱杀烯混剂II(别名)(421)+TX、诱杀烯混剂III(别名)(421)+TX、诱杀烯混剂IV(别名)(421)+TX、醋酸十六烯酯(hexalure)[CCN]+TX、齿小蠹二烯醇(ipsdienol)(别名)[CCN]+TX、小蠢烯醇(ipsenol)(别名)[CCN]+TX、金龟子性诱剂(japonilure)(别名)(481)+TX、里尼汀(lineatin)(别名)[CCN]+TX、利特乐(litlure)(别名)[CCN]+TX、粉纹夜蛾性诱剂(looplure)(别名)[CCN]+TX、诱杀酯(medlure)[CCN]+TX、蒙托么克酸(megatomoicacid)(别名)[CCN]+TX、诱虫醚(methyl eugenol)(别名)(540)+TX、诱虫烯(muscalure)(563)+TX、十八-2,13-二烯-1-基乙酸酯(IUPAC名称)(588)+TX、十八-3,13-二烯-1-基乙酸酯(IUPAC名称)(589)+TX、贺康彼(orfralure)(别名)[CCN]+TX、oryctalure(别名)(317)+TX、非乐康(ostramone)(别名)[CCN]+TX、诱虫环(siglure)[CCN]+TX、索地丁(sordidin)(别名)(736)+TX、食菌甲诱醇(sulcatol)(别名)[CCN]+TX、十四-11-烯-1-基乙酸酯(IUPAC名称)(785)+TX、特诱酮(839)+TX、特诱酮A(别名)(839)+TX、特诱酮B1(别名)(839)+TX、特诱酮B2(别名)(839)+TX、特诱酮C(别名)(839)和创科尔(trunc-call)(别名)[CCN]+TX,
昆虫驱避剂,该昆虫驱避剂选自由以下物质组成的组:2-(辛基硫代)乙醇(IUPAC名称)(591)+TX、避蚊酮(butopyronoxyl)(933)+TX、丁氧基(聚丙二醇)(936)+TX、己二酸二丁酯(IUPAC名称)(1046)+TX、邻苯二甲酸二丁酯(1047)+TX、丁二酸二丁酯(IUPAC名称)(1048)+TX、避蚊胺[CCN]+TX、驱蚊酯(dimethyl carbate)[CCN]+TX、邻苯二甲酸二甲酯[CCN]+TX、乙基己二醇(1137)+TX、己脲[CCN]+TX、甲喹丁(methoquin-butyl)(1276)+TX、甲基新癸酰胺[CCN]+TX、氨羰基甲酸酯(oxamate)[CCN]和羟哌酯[CCN]+TX,
一种杀昆虫剂,该杀昆虫剂选自由以下物质组成的组:1-二氯-1-硝基乙烷(IUPAC/化学文摘名称)(1058)+TX、1,1-二氯-2,2-二(4-乙基苯基)乙烷(IUPAC名称)(1056)+TX、1,2-二氯丙烷(IUPAC/化学文摘名称)(1062)+TX、带有1,3-二氯丙烯的1,2-二氯丙烷(IUPAC名称)(1063)+TX、1-溴-2-氯乙烷(IUPAC/化学文摘名称)(916)+TX、乙酸2,2,2-三氯-1-(3,4-二氯苯基)乙基酯(IUPAC名称)(1451)+TX、2,2-二氯乙烯基2-乙基亚磺酰基乙基甲基磷酸酯(IUPAC名称)(1066)+TX、二甲基氨基甲酸2-(1,3-二硫杂环戊烷-2-基)苯基酯(IUPAC/化学文摘名称)(1109)+TX、硫氰酸2-(2-丁氧基乙氧基)乙基酯(IUPAC/化学文摘名称)(935)+TX、甲基氨基甲酸2-(4,5-二甲基-1,3-二氧环戊烷-2-基)苯基酯(IUPAC/化学文摘名称)(1084)+TX、2-(4-氯-3,5-二甲苯基氧基)乙醇(IUPAC名称)(986)+TX、2-氯乙烯基二乙基磷酸酯(IUPAC名称)(984)+TX、2-咪唑啉酮(IUPAC名称)(1225)+TX、2-异戊酰基茚满-1,3-二酮(IUPAC名称)(1246)+TX、甲基氨基甲酸2-甲基(丙-2-炔基)氨基苯基酯(IUPAC名称)(1284)+TX、月桂酸2-硫氰基乙基酯(IUPAC名称)(1433)+TX、3-溴-1-氯丙-1-烯(IUPAC名称)(917)+TX、二甲基氨基甲酸3-甲基-1-苯基吡唑-5-基酯(IUPAC名称)(1283)+TX、甲基氨基甲酸4-甲基(丙-2-炔基)氨基-3,5-二甲苯基酯(IUPAC名称)(1285)+TX、二甲基氨基甲酸5,5-二甲基-3-氧代环己-1-烯基酯(IUPAC名称)(1085)+TX、阿维菌素(1)+TX、乙酰甲胺磷(2)+TX、啶虫脒(4)+TX、家蝇磷(别名)[CCN]+TX、乙酰虫腈[CCN]+TX、氟丙菊酯(9)+TX、丙烯腈(IUPAC名称)(861)+TX、棉铃威(15)+TX、涕灭威(16)+TX、涕灭砜威(863)+TX、氯甲桥萘(864)+TX、烯丙菊酯(17)+TX、阿洛氨菌素(别名)[CCN]+TX、除害威(866)+TX、α-氯氰菊酯(202)+TX、α-蜕皮激素[CCN](别名)+TX、磷化铝(640)+TX、赛硫磷(870)+TX、硫代酰胺(872)+TX、灭害威(873)+TX、胺吸磷(875)+TX、胺吸磷草酸氢盐(875)+TX、双甲脒(24)+TX、新烟碱(877)+TX、乙基杀扑磷(883)+TX、AVI 382(化合物代码)+TX、AZ 60541(化合物代码)+TX、印楝素(别名)(41)+TX、甲基吡啶磷(42)+TX、谷硫磷-乙基(44)+TX、谷硫磷-甲基(45)+TX、偶氮磷(889)+TX、苏云金芽孢杆菌δ内毒素类(别名)(52)+TX、六氟硅酸钡(别名)[CCN]+TX、多硫化钡(IUPAC/化学文摘名称)(892)+TX、熏菊酯[CCN]+TX、Bayer 22/190(研究代码)(893)+TX、Bayer 22408(研究代码)(894)+TX、噁虫威(58)+TX、丙硫克百威(60)+TX、杀虫磺(66)+TX、β氟氯氰菊酯(194)+TX、β-氯氰菊酯(203)+TX、联苯菊酯(76)+TX、生物烯丙菊酯(78)+TX、生物烯丙菊酯S-环戊烯基异构体(别名)(79)+TX、戊环苄呋菊酯(bioethanomethrin)[CCN]+TX、生物氯菊酯(908)+TX、除虫菊酯(80)+TX、二(2-氯乙基)醚(IUPAC名称)(909)+TX、双三氟虫脲(83)+TX、硼砂(86)+TX、溴灭菊酯(别名)+TX、溴苯烯磷(914)+TX、溴杀烯(918)+TX、溴-DDT(别名)[CCN]+TX、溴硫磷(920)+TX、溴硫磷-乙基(921)+TX、合杀威(924)+TX、噻嗪酮(99)+TX、畜虫威(926)+TX、脱甲基丁嘧啶磷(butathiofos)(927)+TX、丁酮威(103)+TX、丁酯膦(932)+TX、丁酮砜威(104)+TX、丁基哒螨灵(别名)+TX、硫线磷(109)+TX、砷酸钙[CCN]+TX、氰化钙(444)+TX、多硫化钙(IUPAC名称)(111)+TX、毒杀芬(941)+TX、氯灭杀威(943)+TX、甲萘威(115)+TX、克百威(118)+TX、二硫化碳(IUPAC/化学文摘名称)(945)+TX、四氯化碳(IUPAC名称)(946)+TX、三硫磷(947)+TX、丁硫克百成(119)+TX、杀螟丹(123)+TX、杀螟丹盐酸盐(123)+TX、西伐丁(别名)(725)+TX、冰片丹(960)+TX、氯丹(128)+TX、开蓬(963)+TX、杀虫脒(964)+TX、杀虫脒盐酸盐(964)+TX、氯氧磷(129)+TX、溴虫腈(130)+TX、毒虫畏(131)+TX、定虫隆(132)+TX、氯甲磷(136)+TX、氯仿[CCN]+TX、三氯硝基甲烷(141)+TX、氯辛硫磷(989)+TX、灭虫吡啶(990)+TX、毒死蜱(145)+TX、毒死蜱-甲基(146)+TX、虫螨磷(994)+TX、环虫酰肼(150)+TX、灰菊素I(696)+TX、灰菊素II(696)+TX、灰菊素类(696)+TX、顺式苄呋菊酯(cis-resmethrin)(别名)+TX、顺式苄呋菊酯(cismethrin)(80)+TX、功夫菊酯(别名)+TX、除线威(999)+TX、氯氰碘柳胺(别名)[CCN]+TX、噻虫胺(165)+TX、乙酰亚砷酸铜[CCN]+TX、砷酸铜[CCN]+TX、油酸铜[CCN]+TX、蝇毒磷(174)+TX、畜虫磷(1006)+TX、克罗米通(别名)[CCN]+TX、巴毒磷(1010)+TX、克芦磷酯(1011)+TX、冰晶石(别名)(177)+TX、CS 708(研究代码)(1012)+TX、苯腈膦(1019)+TX、杀螟睛(184)+TX、果虫磷(1020)+TX、环虫菊酯[CCN]+TX、乙氰菊酯(188)+TX、氟氯氰菊酯(193)+TX、三氯氟氰菊酯(196)+TX、氯氰菊酯(201)+TX、苯氰菊酯(206)+TX、环丙马秦(209)+TX、畜蜱磷(别名)[CCN]+TX、d-柠檬烯(别名)[CCN]+TX、d-四甲菊酯(别名)(788)+TX、DAEP(1031)+TX、棉隆(216)+TX、DDT(219)+TX、单甲基克百威(decarbofuran)(1034)+TX、溴氰菊酯(223)+TX、田乐磷(1037)+TX、田乐磷-O(1037)+TX、田乐磷-S(1037)+TX、内吸磷(1038)+TX、内吸磷-甲基(224)+TX、内吸磷-O(1038)+TX、内吸磷-O-甲基(224)+TX、内吸磷-S(1038)+TX、内吸磷-S-甲基(224)+TX、内吸磷-S-甲基砜(1039)+TX、丁醚脲(226)+TX、氯亚胺硫磷(1042)+TX、二胺磷(1044)+TX、二嗪磷(227)+TX、异氯磷(1050)+TX、除线磷(1051)+TX、敌敌畏(236)+TX、迪克力弗斯(dicliphos)(别名)+TX、迪克莱赛尔(dicresyl)(别名)[CCN]+TX、百治磷(243)+TX、地昔尼尔(244)+TX、狄氏剂(1070)+TX、二乙基5-甲基吡唑-3-基磷酸酯(IUPAC名称)(1076)+TX、除虫脲(250)+TX、二羟丙茶碱(dilor)(别名)[CCN]+TX、四氟甲醚菊酯[CCN]+TX、甲氟磷(1081)+TX、地麦威(1085)+TX、乐果(262)+TX、苄菊酯(1083)+TX、甲基毒虫畏(265)+TX、敌蝇威(1086)+TX、消螨酚(1089)+TX、消螨酚(dinex-diclexine)(1089)+TX、丙硝酚(1093)+TX、戊硝酚(1094)+TX、达诺杀(1095)+TX、呋虫胺(271)+TX、苯虫醚(1099)+TX、蔬果磷(1100)+TX、二氧威(1101)+TX、敌恶磷(1102)+TX、乙拌磷(278)+TX、苯噻乙双硫磷(dithicrofos)(1108)+TX、DNOC(282)+TX、多拉克汀(别名)[CCN]+TX、DSP(1115)+TX、蜕皮激素(别名)[CCN]+TX、EI 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72129(研究代码)(1397)+TX、亚砷酸钠[CCN]+TX、氰化钠(444)+TX、氟化钠(IUPAC/化学文摘名称)(1399)+TX、六氟硅酸钠(1400)+TX、五氯酚钠(623)+TX、硒酸钠(IUPAC名称)(1401)+TX、硫氰酸钠[CCN]+TX、苏硫磷(1402)+TX、多杀菌素(737)+TX、螺甲螨酯(739)+TX、螺虫乙酯(CCN)+TX、萨尔科福隆(sulcofuron)(746)+TX、萨尔科福隆钠(sulcofuron-sodium)(746)+TX、氟虫胺(750)+TX、治螟磷(753)+TX、磺酰氟(756)+TX、硫丙磷(1408)+TX、焦油类(别名)(758)+TX、τ-氟胺氰菊酯(398)+TX、噻螨威(1412)+TX、TDE(1414)+TX、虫酰肼(762)+TX、吡螨胺(763)+TX、丁基嘧啶磷(764)+TX、氟苯脲(768)+TX、七氟菊酯(769)+TX、双硫磷(770)+TX、TEPP(1417)+TX、环戊烯丙菊酯(1418)+TX、叔丁威(terbam)(别名)+TX、特丁硫磷(773)+TX、四氯乙烷[CCN]+TX、杀虫畏(777)+TX、四甲菊酯(787)+TX、θ氯氰菊酯(204)+TX、噻虫啉(791)+TX、塞芬诺克斯(thiafenox)(别名)+TX、噻虫嗪(792)+TX、苯噻硫磷(thicrofos)(1428)+TX、克虫威(1431)+TX、杀虫环(798)+TX、杀虫环草酸氢盐(798)+TX、硫双威(799)+TX、久效威(800)+TX、甲基乙拌磷(801)+TX、虫线磷(1434)+TX、杀虫单(thiosultap)(803)+TX、杀虫双(thiosultap-sodium)(803)+TX、苏云金素(别名)[CCN]+TX、唑虫酰胺(809)+TX、四溴菊酯(812)+TX、四氟苯菊酯(813)+TX、反式苄氯菊酯(transpermethrin)(1440)+TX、威菌磷(1441)+TX、唑蚜威(818)+TX、三唑磷(820)+TX、唑呀威(别名)+TX、敌百虫(824)+TX、三氯偏磷酸-3(trichlormetaphos-3)(别名)[CCN]+TX、毒壤膦(1452)+TX、三氯丙氧磷(1455)+TX、杀铃脲(835)+TX、混杀威(840)+TX、烯虫硫酯(1459)+TX、蚜灭磷(847)+TX、甲烯氟虫腈(vaniliprole)[CCN]+TX、藜芦定(别名)(725)+TX、藜芦碱(别名)(725)+TX、XMC(853)+TX、灭杀威(854)+TX、YI-5302(化合物代码)+TX、ζ-氯氰菊酯(205)+TX、泽塔米林(zetamethrin)(别名)+TX、磷化锌(640)+TX、丙硫恶唑磷(zolaprofos)(1469)以及ZXI 8901(研究代码)(858)+TX、氰虫酰胺[736994-63-19]+TX、氯虫酰胺[500008-45-7]+TX、唑螨氰(cyenopyrafen)[560121-52-0]+TX、丁氟螨酯[400882-07-7]+TX、氟虫吡喹(pyrifluquinazon)[337458-27-2]+TX、乙基多杀菌素(spinetoram)[187166-40-1+187166-15-0]+TX、螺虫乙酯[203313-25-1]+TX、砜虫啶(sulfoxaflor)[946578-00-3]+TX、丁虫腈(flufiprole)[704886-18-0]+TX、氯氟醚菊酯[915288-13-0]+TX、四氟醚菊酯(tetramethylfluthrin)[84937-88-2]+TX、triflumezopyrim(披露于WO2012/092115中)+TX,fluxametamide(WO 2007/026965)+TX、epsilon-甲氧苄氟菊酯[240494-71-7]+TX、epsilon-momfluorothrin[1065124-65-3]+TX、fluazaindolizine[1254304-22-7]+TX、氯碱丙炔菊酯[399572-87-3]+TX、fluxametamide[928783-29-3]+TX、cyhalodiamide[1262605-53-7]+TX、tioxazafen[330459-31-9]+TX、broflanilide[1207727-04-5]+TX、丁烯氟虫腈(flufiprole)[704886-18-0]+TX、环溴虫酰胺[1031756-98-5]+TX、氟氰虫酰胺[1229654-66-3]+TX、戊吡虫胍(描述于WO 2010/060231中)+TX、环氧虫啶(描述于WO 2005/077934中)+TX,spiropidion+TX、Afidopyropen+TX、flupyrimin+TX、Momfluorothrin+TX、κ-联苯菊酯+TX、κ-七氟菊酯+TX、Dichloromezotiaz+TX、Tetrachloraniliprole+TX、benzpyrimoxan+TX
杀软体动物剂,该杀软体动物剂选自由以下物质组成的组:二(三丁基锡)氧化物(IUPAC名称)(913)+TX、溴乙酰胺[CCN]+TX、砷酸钙[CCN]+TX、除线威(cloethocarb)(999)+TX、乙酰亚砷酸铜[CCN]+TX、硫酸铜(172)+TX、三苯锡(347)+TX、磷酸铁(IUPAC名称)(352)+TX、四聚乙醛(518)+TX、灭虫威(530)+TX、氯硝柳胺(576)+TX、氯硝柳胺乙醇胺盐(576)+TX、五氯酚(623)+TX、五氯苯氧化钠(623)+TX、噻螨威(tazimcarb)(1412)+TX、硫双威(799)+TX、三丁基氧化锡(913)+TX、杀螺吗啉(trifenmorph)(1454)+TX、混杀威(trimethacarb)(840)+TX、乙酸三苯基锡(IUPAC名称)(347)和三苯基氢氧化锡(IUPAC名称)(347)+TX、皮瑞普(pyriprole)[394730-71-3]+TX,
杀线虫剂,该杀线虫剂选自由以下物质组成的组:AKD-3088(化合物代码)+TX、1,2-二溴-3-氯丙烷(IUPAC/化学文摘名)(1045)+TX、1,2-二氯丙烷(IUPAC/化学文摘名)(1062)+TX、1,2-二氯丙烷与1,3-二氯丙烯(IUPAC名称)(1063)+TX、1,3-二氯丙烯(233)+TX、3,4-二氯四氢噻吩1,1-二氧化物(IUPAC/化学文摘名)(1065)+TX、3-(4-氯苯基)-5-甲基绕丹宁(IUPAC名称)(980)+TX、5-甲基-6-硫代-1,3,5-噻二嗪烷-3-基乙酸(IUPAC名称)(1286)+TX、6-异戊烯基氨基嘌呤(别名)(210)+TX、阿巴美丁(1)+TX、乙酰虫腈[CCN]+TX、棉铃威(15)+TX、涕灭威(aldicarb)(16)+TX、涕灭砜威(aldoxycarb)(863)+TX、AZ 60541(化合物代码)+TX、benclothiaz[CCN]+TX、苯菌灵(62)+TX、丁基哒螨酮(butylpyridaben)(别名)+TX、硫线磷(cadusafos)(109)+TX、克百威(carbofuran)(118)+TX、二硫化碳(945)+TX、丁硫克百威(119)+TX、氯化苦(141)+TX、毒死蜱(145)+TX、除线威(cloethocarb)(999)+TX、细胞分裂素(cytokinins)(别名)(210)+TX,棉隆(216)+TX、DBCP(1045)+TX、DCIP(218)+TX、除线特(diamidafos)(1044)+TX、除线磷(dichlofenthion)(1051)+TX、二克磷(dicliphos)(别名)+TX、乐果(262)+TX、多拉克汀(别名)[CCN]+TX、依马克丁(291)+TX、依马克丁苯甲酸酯(291)+TX、依立诺克丁(别名)[CCN]+TX、灭线磷(312)+TX、二溴乙烷(316)+TX、苯线磷(fenamiphos)(326)+TX、吡螨胺(别名)+TX、丰索磷(fenpyrad)(1158)+TX、噻唑磷(fosthiazate)(408)+TX、丁硫环磷(fosthietan)(1196)+TX、糠醛(别名)[CCN]+TX、GY-81(研究代码)(423)+TX、速杀硫磷(heterophos)[CCN]+TX、碘甲烷(IUPAC名称)(542)+TX、isamidofos(1230)+TX、氯唑磷(isazofos)(1231)+TX、伊维菌素(别名)[CCN]+TX、激动素(210)+TX、甲基灭蚜磷(mecarphon)(1258)+TX、威百亩(519)+TX、威百亩钾盐(别名)(519)+TX、威百亩钠盐(519)+TX、甲基溴(537)+TX、异硫氰酸甲酯(543)+TX、杀螨菌素肟(milbemycin oxime)(别名)[CCN]+TX、莫昔克丁(剔名)[CCN]+TX、疣孢漆斑菌(Myrothecium verrucaria)组分(别名)(565)+TX、NC-184(化合物代码)+TX、杀线威(602)+TX、甲拌磷(636)+TX、磷胺(639)+TX、磷虫威(phosphocarb)[CCN]+TX、硫线磷(sebufos)(别名)+TX、塞拉菌素(selamectin)(别名)[CCN]+TX、多杀菌素(737)+TX、叔丁威(terbam)(别名)+TX、特丁磷(terbufos)(773)+TX、四氯噻吩(IUPAC/化学文摘名)(1422)+TX、噻菲农(别名)+TX、虫线磷(thionazin)(1434)+TX、三唑磷(triazophos)(820)+TX、triazuron(别名)+TX、二甲苯酚[CCN]+TX、YI-5302(化合物代码)和玉米素(别名)(210)+TX、fluensulfone[318290-98-1]+TX、氟吡菌酰胺(fluopyram)+TX,
硝化作用抑制剂,该硝化作用抑制剂选自由以下物质组成的组:乙基黄原酸钾[CCN]以及氯啶(nitrapyrin)(580)+TX,
植物激活剂,该植物激活剂选自由以下物质组成的组:噻二唑素(acibenzolar)(6)+TX、噻二唑素-S-甲基(6)+TX、烯丙苯噻唑(probenazole)(658)和大虎杖(Reynoutriasachalinensis)提取物(别名)(720)+TX,
杀鼠剂,该杀鼠剂选自由以下物质组成的组:2-异戊酰茚满-1,3-二酮(IUPAC名称)(1246)+TX、4-(喹喔啉-2-基氨基)苯磺酰胺(IUPAC名称)(748)+TX、α-氯代醇[CCN]+TX、磷化铝(640)+TX、安妥(880)+TX、三氧化二砷(882)+TX、碳酸钡(891)+TX、双鼠脲(912)+TX、溴鼠隆(89)+TX、溴敌隆(91)+TX、溴鼠胺(92)+TX、氰化钙(444)+TX、氮醛糖(127)+TX、氯鼠酮(140)+TX、维生素D3(别名)(850)+TX、氯灭鼠灵(1004)+TX、克灭鼠(1005)+TX、杀鼠萘(175)+TX、杀鼠嘧啶(1009)+TX、鼠得克(246)+TX、噻鼠灵(249)+TX、敌鼠钠(273)+TX、维生素D2(301)+TX、氟鼠灵(357)+TX、氟乙酰胺(379)+TX、鼠朴定(1183)+TX、盐酸鼠朴定(1183)+TX、γ-HCH(430)+TX、HCH(430)+TX、氢氰酸(444)+TX、碘甲烷(IUPAC名称)(542)+TX、林旦(430)+TX、磷化镁(IUPAC名称)(640)+TX、甲基溴(537)+TX、鼠特灵(1318)+TX、毒鼠磷(1336)+TX、磷化氢(IUPAC名称)(640)+TX、磷[CCN]+TX、杀鼠酮(1341)+TX、亚砷酸钾[CCN]+TX、灭鼠优(1371)+TX、海葱糖苷(1390)+TX、亚砷酸钠[CCN]+TX、氰化钠(444)+TX、氟乙酸钠(735)+TX、士的宁(745)+TX、硫酸铊[CCN]+TX、杀鼠灵(851)以及磷化锌(640)+TX,
增效剂,该增效剂选自由以下物质组成的组:2-(2-丁氧基乙氧基)乙基胡椒基酯(IUPAC名称)(934)+TX、5-(1,3-苯并二氧杂环戊烯-5-基)-3-己基环己-2-烯酮(IUPAC名称)(903)+TX、具有橙花叔醇的法呢醇(别名)(324)+TX、MB-599(研究代码)(498)+TX、MGK264(研究代码)(296)+TX,增效醚(piperonyl butoxide)(649)+TX、增效醛(piprotal)(1343)+TX、增效酯(propyl isomer)(1358)+TX、S421(研究代码)(724)+TX、增效散(sesamex)(1393)+TX、芝麻林素(sesasmolin)(1394)和亚砜(1406)+TX,
动物驱避剂,该动物驱避剂选自由以下物质组成的组:蒽醌(32)+TX、氯醛糖(127)+TX、环烷酸铜[CCN]+TX、王铜(171)+TX、二嗪磷(227)+TX、二环戊二烯(化学名称)(1069)+TX、双胍盐(guazatine)(422)+TX、双胍醋酸盐(422)+TX、灭虫威(530)+TX、吡啶-4-胺(IUPAC名称)(23)+TX、塞仑(804)+TX、混杀威(trimethacarb)(840)+TX、环烷酸锌[CCN]和福美锌(856)+TX,
杀病毒剂,该杀病毒剂选自由以下物质组成的组:衣马宁(别名)[CCN]和利巴韦林(别名)[CCN]+TX,
创伤保护剂,该创伤保护剂选自由以下物质组成的组:氧化汞(512)+TX、辛噻酮(590)和甲基硫菌灵(802)+TX,
以及生物活性化合物,这些化合物选自由以下物质组成的组:阿扎康唑[60207-31-0]+TX、联苯三唑醇[70585-36-3]+TX、糠菌唑[116255-48-2]+TX、环唑醇[94361-06-5]+TX、苯醚甲环唑[119446-68-3]+TX、烯唑醇[83657-24-3]+TX、氟环唑[106325-08-0]+TX、腈苯唑[114369-43-6]+TX、氟喹唑[136426-54-5]+TX、氟硅唑[85509-19-9]+TX、粉唑醇[76674-21-0]+TX、己唑醇[79983-71-4]+TX、抑霉唑[35554-44-0]+TX、亚胺唑[86598-92-7]+TX、种菌唑[125225-28-7]+TX、叶菌唑[125116-23-6]+TX、腈菌唑[88671-89-0]+TX、稻瘟酯[101903-30-4]+TX、戊菌唑[66246-88-6]+TX、丙硫菌唑[178928-70-6]+TX、啶斑肟(pyrifenox)[88283-41-4]+TX、丙氯灵[67747-09-5]+TX、丙环唑[60207-90-1]+TX、硅氟唑(simeconazole)[149508-90-7]+TX、戊唑醇[107534-96-3]+TX、氟醚唑[112281-77-3]+TX、三唑酮[43121-43-3]+TX、三唑酮[55219-65-3]+TX、氟菌唑[99387-89-0]+TX、灭菌唑[131983-72-7]+TX、三环苯嘧醇[12771-68-5]+TX、氯苯嘧啶醇[60168-88-9]+TX、氟氯苯嘧啶醇[63284-71-9]+TX、乙嘧酚磺酸酯(bupirimate)[41483-43-6]+TX、甲菌定(dimethirimol)[5221-53-4]+TX、乙菌定(ethirimol)[23947-60-6]+TX、十二环吗啉[1593-77-7]+TX、苯锈啶(fenpropidine)[67306-00-7]+TX、丁苯吗啉[67564-91-4]+TX、螺环菌胺[118134-30-8]+TX、十三吗啉[81412-43-3]+TX、嘧菌环胺[121552-61-2]+TX、嘧菌胺[110235-47-7]+TX、嘧霉胺(pyrimethanil)[53112-28-0]+TX、拌种咯[74738-17-3]+TX、咯菌腈(fludioxonil)[131341-86-1]+TX、苯霜灵(benalaxyl)[71626-11-4]+TX、呋霜灵(furalaxyl)[57646-30-7]+TX、甲霜灵[57837-19-1]+TX、R甲霜灵[70630-17-0]+TX、呋酰胺[58810-48-3]+TX、恶霜灵(Oxadixyl)[77732-09-3]+TX、苯菌灵[17804-35-2]+TX、多菌灵[10605-21-7]+TX、咪菌威(debacarb)[62732-91-6]+TX、麦穗宁[3878-19-1]+TX、噻苯达唑[148-79-8]+TX、乙菌利(chlozolinate)[84332-86-5]+TX、菌核利(dichlozoline)[24201-58-9]+TX、异菌脲(Iprodione)[36734-19-7]+TX、myclozoline[54864-61-8]+TX、腐霉利(procymidone)[32809-16-8]+TX、乙烯菌核利(vinclozoline)[50471-44-8]+TX、啶酰菌胺(boscalid)[188425-85-6]+TX、萎锈灵[5234-68-4]+TX、甲呋酰苯胺[24691-80-3]+TX、氟酰胺(Flutolanil)[66332-96-5]+TX、灭锈胺[55814-41-0]+TX、氧化萎锈灵[5259-88-1]+TX、吡噻菌胺(penthiopyrad)[183675-82-3]+TX、噻呋菌胺[130000-40-7]+TX、双胍盐[108173-90-6]+TX、多果定(dodine)[2439-10-3][112-65-2](游离键)+TX、双胍辛胺(iminoctadine)[13516-27-3]+TX、嘧菌酯[131860-33-8]+TX、醚菌胺[149961-52-4]+TX、烯肟菌酯{Proc.BCPC,Int.Congr.,Glasgow.2003,1,93}+TX、氟嘧菌酯[361377-29-9]+TX、甲基醚菌酯[143390-89-0]+TX、苯氧菌胺[133408-50-1]+TX、肟菌酯[141517-21-7]+TX、肟醚菌胺[248593-16-0]+TX、啶氧菌酯[117428-22-5]+TX、唑菌胺酯[175013-18-0]+TX、福美铁[14484-64-1]+TX、代森锰锌[8018-01-7]+TX、代森锰[12427-38-2]+TX、代森联[9006-42-2]+TX、甲代森锌(propineb)[12071-83-9]+TX、塞仑[137-26-8]+TX、代森锌[12122-67-7]+TX、福美锌[137-30-4]+TX、敌菌丹(captafol)[2425-06-1]+TX、克菌丹[133-06-2]+TX、苯氟磺胺[1085-98-9]+TX、唑啶草(fluoroimide)[41205-21-4]+TX、灭菌丹[133-07-3]+TX、甲苯氟磺胺[731-27-1]+TX、波尔多(bordeaux)混合物[8011-63-0]+TX、氢氧化铜(copperhydroxid)[20427-59-2]+TX、氯化铜(copperoxychlorid)[1332-40-7]+TX、硫酸铜(coppersulfat)[7758-98-7]+TX、氧化铜(copperoxid)[1317-39-1]+TX、代森锰铜(mancopper)[53988-93-5]+TX、喹啉铜(oxine-copper)[10380-28-6]+TX、敌螨普(dinocap)[131-72-6]+TX、酞菌酯(nitrothal-isopropyl)[10552-74-6]+TX、克瘟散[17109-49-8]+TX、异稻瘟净(iprobenphos)[26087-47-8]+TX、稻瘟灵(isoprothiolane)[50512-35-1]+TX、氯瘟磷(phosdiphen)[36519-00-3]+TX、克菌磷(pyrazophos)[13457-18-6]+TX、甲基托氯磷(tolclofos-methyl)[57018-04-9]+TX、苯并噻二唑(acibenzolar-S-methyl)[135158-54-2]+TX、敌菌灵[101-05-3]+TX、苯噻菌胺[413615-35-7]+TX、灭瘟素(blasticidin)-S[2079-00-7]+TX、灭螨猛(chinomethionat)[2439-01-2]+TX、地茂散(chloroneb)[2675-77-6]+TX、百菌清[1897-45-6]+TX、环氟菌胺[180409-60-3]+TX、霜脲氰[57966-95-7]+TX、二氯萘醌(dichlone)[117-80-6]+TX、双氯氰菌胺(diclocymet)[139920-32-4]+TX、哒菌酮(diclomezine)[62865-36-5]+TX、氯硝胺(dicloran)[99-30-9]+TX、乙霉威(diethofencarb)[87130-20-9]+TX、烯酰吗啉[110488-70-5]+TX、SYPLI90(Flumorph)[211867-47-9]+TX、二噻农(dithianon)[3347-22-6]+TX、噻唑菌胺(ethaboxam)[162650-77-3]+TX、土菌灵(etridiazole)[2593-15-9]+TX、恶唑菌酮[131807-57-3]+TX、咪唑菌酮(fenamidone)[161326-34-7]+TX、稻瘟酰胺(Fenoxanil)[115852-48-7]+TX、三苯锡(fentin)[668-34-8]+TX、嘧菌腙(ferimzone)[89269-64-7]+TX、氟啶胺(fluazinam)[79622-59-6]+TX、氟吡菌胺(fluopicolide)[239110-15-7]+TX、磺菌胺(flusulfamide)[106917-52-6]+TX、环酰菌胺[126833-17-8]+TX、福赛得(fosetyl-aluminium)[39148-24-8]+TX、恶霉灵(hymexazol)[10004-44-1]+TX、丙森锌[140923-17-7]+TX、IKF916(赛座灭(Cyazofamid))[120116-88-3]+TX、春雷霉素(kasugamycin)[6980-18-3]+TX、磺菌威(methasulfocarb)[66952-49-6]+TX、苯菌酮[220899-03-6]+TX、戊菌隆(pencycuron)[66063-05-6]+TX、苯酞[27355-22-2]+TX、多氧霉素(polyoxins)[11113-80-7]+TX、噻菌灵(probenazole)[27605-76-1]+TX、百维威(propamocarb)[25606-41-1]+TX、碘喹唑酮(proquinazid)[189278-12-4]+TX、乐喹酮(pyroquilon)[57369-32-1]+TX、喹氧灵[124495-18-7]+TX、五氯硝苯[82-68-8]+TX、硫[7704-34-9]+TX、噻酰菌胺[223580-51-6]+TX、咪唑嗪(triazoxide)[72459-58-6]+TX、三环唑[41814-78-2]+TX、嗪氨灵[26644-46-2]+TX、有效霉素[37248-47-8]+TX、苯酰菌胺(zoxamide)(RH7281)[156052-68-5]+TX、双炔酰菌胺(mandipropamid)[374726-62-2]+TX、吡蚜酮(isopyrazam)[881685-58-1]+TX、塞德因(sedaxane)[874967-67-6]+TX、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(9-二氯亚甲基-1,2,3,4-四氢-1,4-桥亚甲基-萘-5-基)-酰胺(披露于WO 2007/048556中)+TX、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(3’,4’,5’-三氟-联苯基-2-基)-酰胺(披露于WO 2006/087343中)+TX、[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(环丙基羰基)氧基]-1,3,4,4a,5,6,6a,12,12a,12b-十氢-6,12-二羟基-4,6a,12b-三甲基-11-氧代-9-(3-吡啶基)-2H,11H萘并[2,1-b]吡喃并[3,4-e]吡喃-4-基]甲基-环丙甲酸酯[915972-17-7]+TX以及1,3,5-三甲基-N-(2-甲基-1-氧丙基)-N-[3-(2-甲基丙基)-4-[2,2,2-三氟-1-甲氧基-1-(三氟甲基)乙基]苯基]-1H-吡唑-4-甲酰胺[926914-55-8]+TX;以及
微生物剂,包括:鲁氏不动杆菌+TX、交替枝顶孢(Acremonium alternatum)+TX+TX、顶头孢霉(Acremonium cephalosporium)+TX+TX、Acremonium diospyri+TX、Acremonium obclavatum+TX、棉褐带卷蛾颗粒体病毒(AdoxGV)+TX、放射形土壤杆菌菌株K84(Galltrol-/>)+TX、互隔链格孢+TX、决明链格孢(Alternaria cassia)+TX、损毁链格孢/>+TX、白粉寄生孢/>+TX、黄曲霉AF36/>+TX、黄曲霉NRRL 21882/>+TX、曲霉属+TX、出芽短梗霉+TX、固氮螺菌属+TX、(/>+TX、/>)+TX、固氮菌属+TX、圆褐固氮菌/>+TX、孢囊固氮菌(Bionatural Blooming/>)+TX、解淀粉芽孢杆菌+TX、蜡样芽孢杆菌+TX、原生祛病芽孢杆菌(Bacillus chitinosporus)菌株CM-1+TX、原生祛病芽孢杆菌菌株AQ746+TX、地衣芽孢杆菌菌株HB-2(BiostartTM/>)+TX、地衣芽孢杆菌菌株3086(/>+TX、Green/>)+TX、环状芽孢杆菌+TX、坚硬芽孢杆菌(+TX、BioNem-/>+TX、/>)+TX、坚硬芽孢杆菌菌株I-1582+TX、浸麻芽孢杆菌+TX、Bacillus marismortui+TX、巨大芽孢杆菌+TX、蕈状芽孢杆菌菌株AQ726+TX、日本甲虫芽孢杆菌(Milky Spore/>)+TX、短小芽孢杆菌属+TX、短小芽孢杆菌菌株GB34(Yield/>)+TX、短小芽孢杆菌菌株AQ717+TX、短小芽孢杆菌菌株QST2808(/>+TX、Ballad/>)+TX、球形芽孢杆菌/>+TX、芽孢杆菌属+TX、芽孢杆菌属菌株AQ175+TX、芽孢杆菌属菌株AQ177+TX、芽孢杆菌属菌株AQ178+TX、枯草芽孢杆菌菌株QST 713(/>+TX、/>+TX、/>)+TX、枯草芽孢杆菌菌株QST 714/>+TX、枯草芽孢杆菌菌株AQ153+TX、枯草芽孢杆菌菌株AQ743+TX、枯草芽孢杆菌菌株QST3002+TX、枯草芽孢杆菌菌株QST3004+TX、枯草芽孢杆菌解淀粉变种菌株FZB24(/>+TX、/>)+TX、苏云金芽孢杆菌Cry 2Ae+TX、苏云金芽孢杆菌Cry1Ab+TX、苏云金芽孢杆菌鲇泽亚种(Bacillus thuringiensis aizawai)GC 91/>+TX、苏云金芽孢杆菌以色列亚种(Bacillus thuringiensisisraelensis)(/>+TX、/>+TX、/>)+TX、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensis kurstaki)(/>+TX、/>+TX、+TX、/>+TX、Scutella/>+TX、Turilav/>+TX、/>+TX、Dipel/>+TX、/>+TX、/>)+TX、苏云金芽孢杆菌库尔斯塔克亚种BMP123/>+TX、苏云金芽孢杆菌库尔斯塔克亚种HD-1(Bioprotec-CAF//>)+TX、苏云金芽孢杆菌菌株BD#32+TX、苏云金芽孢杆菌菌株AQ52+TX、苏云金芽孢杆菌鲇泽变种(/>+TX、/>)+TX、细菌属(/>+TX、+TX、/>)+TX、密执安棍状杆菌(Clavipactermichiganensis)的噬菌体/>+TX、/>+TX、球孢白僵菌(+TX、Brocaril/>)+TX、球孢白僵菌GHA(Mycotrol/>+TX、Mycotrol+TX、/>)+TX、布氏白僵菌(/>+TX、Schweizer+TX、/>)+TX、白僵菌属+TX、灰葡萄孢霉+TX、大豆慢生型根瘤菌+TX、短短小芽孢杆菌+TX、苏云金芽孢杆菌拟步行甲亚种(Bacillusthuringiensis tenebrionis)/>+TX、BtBooster+TX、洋葱伯克霍尔德菌(+TX、/>+TX、Blue/>)+TX、伯克霍尔德菌(Burkholderiagladii)+TX、唐菖蒲伯克霍尔德菌+TX、伯克霍尔德菌属+TX、加拿大蓟真菌(CBH Canadian)+TX、奶酪假丝酵母+TX、无名假丝酵母+TX、Candida fructus+TX、光滑念珠菌+TX、吉利蒙念珠菌(Candida guilliermondii)+TX、口津假丝酵母+TX、橄榄假丝酵母菌株O+TX、近平滑假丝酵母+TX、菌膜假丝酵母+TX、铁红假丝酵母+TX、拉考夫假丝酵母(Candida reukaufii)+TX、齐藤假丝酵母(Candida saitoana)(Bio-/>+TX、)+TX、清酒假丝酵母+TX、假丝酵母属+TX、纤细假丝酵母+TX、戴氏西地西菌(Cedecea dravisae)+TX、产黄纤维单胞菌+TX、螺卷毛壳(Nova-/>)+TX、球毛壳菌(Nova-/>)+TX、铁杉紫色杆菌(Chromobacterium subtsugae)菌株PRAA4-1T+TX、枝状枝孢菌+TX、尖孢枝孢+TX、Cladosporium chlorocephalum+TX、枝孢属+TX、极细枝孢霉+TX、粉红粘帚霉/>+TX、尖孢炭疽菌(Colletotrichum acutatum)+TX、盾壳霉(Cotans/>)+TX、盾壳霉属+TX、浅白隐球酵母/>+TX、土生隐球菌+TX、Cryptococcus infirmo-miniatus+TX、罗伦隐球酵母+TX、苹果异形小卷蛾颗粒体病毒/>+TX、坎平贪铜菌(Cupriaviduscampinensis)+TX、苹果蠹蛾颗粒体病毒(CYD-/>)+TX、苹果蠹蛾颗粒体病毒(/>+TX、Madex/>+TX、Madex Max//>)+TX、Cylindrobasidium laeve+TX、枝双孢霉属+TX、Drechslera hawaiinensis+TX、阴沟肠杆菌+TX、肠杆菌科+TX、毒力虫霉(/>+TX、黑附球菌(Epicoccum nigrum)+TX、黑附球菌(Epicoccum purpurascens)+TX、附球菌属+TX、花状线黑粉菌(Filobasidium floriforme)+TX、锐顶镰孢菌+TX、厚垣镰孢霉+TX、尖镰孢(/>/Biofox/>)+TX、层生镰孢+TX、镰孢属+TX、溶磷白地霉(Galactomyces geotrichum)+TX、链孢粘帚霉(/>+TX、/>)+TX、粉红粘帚霉+TX、粘帚霉属/>+TX、绿色粘帚霉+TX、颗粒体病毒属/>+TX、嗜盐盐芽孢杆菌(Halobacillus halophilus)+TX、沿岸盐芽孢杆菌(Halobacillus litoralis)+TX、特氏盐芽孢杆菌(Halobacillus trueperi)+TX、盐单胞菌属+TX、冰下盐单胞菌(Halomonassubglaciescola)+TX、盐弧菌变型(Halovibrio variabilis)+TX、葡萄汁有孢汉逊酵母+TX、棉铃虫核型多角体病毒/>+TX、玉米穗虫核型多角体病毒+TX、异黄酮-芒柄花黄素/>+TX、柠檬克勒克酵母+TX、克勒克酵母属+TX、大链壶菌(Lagenidium giganteum)/>+TX、长孢蜡蚧菌(Lecanicillium longisporum)/>+TX、蜡蚧轮枝菌(Lecanicilliummuscarium)/>+TX、舞毒蛾核多角体病毒/>+TX、嗜盐海球菌+TX、格氏梅拉菌(Meira geulakonigii)+TX、绿僵菌/>+TX、绿僵菌(Destruxin)+TX、Metschnikowia fruticola/>+TX、美极梅奇酵母(Metschnikowiapulcherrima)+TX、Microdochium dimerum/>+TX、蓝色小单孢菌(Micromonospora coerulea)+TX、Microsphaeropsis ochracea+TX、Muscodor albus 620+TX、Muscodor roseus菌株A3-5+TX、菌根属(Mycorrhizae spp.)(+TX、Root/>)+TX、疣孢漆斑菌菌株AARC-0255/>+TX、BROS/>+TX、Ophiostoma piliferum菌株D97/>+TX、粉质拟青霉(Paecilomyces farinosus)+TX、玫烟色拟青霉(PFR-/>+TX、/>)+TX、淡紫拟青霉(Paecilomyces linacinus)(Biostat/>)+TX、淡紫拟青霉菌株251(MeloCon)+TX、多粘类芽孢杆菌+TX、成团泛菌(BlightBan C9-/>)+TX、泛菌属+TX、巴斯德氏芽菌属/>+TX、Pasteuria nishizawae+TX、黄灰青霉+TX、Penicilliumbillai(/>+TX、/>)+TX、短密青霉+TX、常现青霉+TX、灰黄青霉+TX、产紫青霉+TX、青霉菌属+TX、纯绿色肯霉+TX、大伏革菌(Phlebiopsis gigantean)+TX、解磷细菌/>+TX、隐地疫霉+TX、棕榈疫霉+TX、异常毕赤酵母+TX、Pichia guilermondii+TX、膜醭毕赤氏酵母+TX、指甲毕赤酵母+TX、树干毕赤酵母+TX、铜绿假单胞菌+TX、致金色假单胞菌(Pseudomonasaureofasciens)(Spot-Less/>)+TX、洋葱假单胞菌+TX、绿针假单胞菌+TX、皱褶假单胞菌(Pseudomonas corrugate)+TX、荧光假单胞菌菌株A506(BlightBan/>)+TX、恶臭假单胞菌+TX、Pseudomonas reactans+TX、假单胞菌属+TX、丁香假单胞菌(Bio-/>)+TX、绿黄假单胞菌+TX、荧光假单胞菌/>+TX、Pseudozyma flocculosa菌株PF-A22 UL(Sporodex/>)+TX、纵沟柄锈菌(Pucciniacanaliculata)+TX、Puccinia thlaspeos(WO od/>)+TX、侧雄腐霉菌(Pythiumparoecandrum)+TX、寡雄腐霉(/>+TX、/>)+TX、缠器腐霉+TX、水生拉恩菌(Rhanella aquatilis)+TX、拉恩菌属+TX、根瘤菌(/>+TX、)+TX、丝核菌属+TX、球状红球菌菌株AQ719+TX、双倒卵形红冬孢酵母菌(Rhodosporidium diobovatum)+TX、圆红冬孢酵母菌+TX、红酵母属+TX、粘红酵母+TX、禾本红酵母+TX、胶红酵母(Rhodotorula mucilagnosa)+TX、深红酵母+TX、酿酒酵母+TX、玫瑰色盐水球菌(Salinococcus roseus)+TX、小核盘菌+TX、小核盘菌/>+TX、柱顶孢霉属+TX、Scytalidium uredinicola+TX、甜菜夜蛾核型多角体病毒(Spod-/>+TX、)+TX、粘质沙雷氏菌+TX、普城沙雷菌+TX、沙雷氏菌属+TX、粪生粪壳菌+TX、海灰翅夜蛾核型多角体病毒/>+TX、红掷孢酵母+TX、嗜麦芽寡养单胞菌+TX、不吸水链霉菌+TX、白丘链霉菌(Streptomyces albaduncus)+TX、脱叶链霉菌+TX、鲜黄链霉菌+TX、灰平链霉菌+TX、灰绿链霉菌/>+TX、利迪链霉菌/>+TX、利迪链霉菌WYEC-108/>+TX、紫色链霉菌+TX、小铁艾酵母(Tilletiopsisminor)+TX、铁艾酵母属+TX、棘孢木霉(T34/>)+TX、盖姆斯木霉(Trichodermagamsii)/>+TX、深绿木霉/>+TX、钩状木霉TH 382+TX、里法哈茨木霉(Trichoderma harzianum rifai)/>+TX、哈茨木霉T-22(Trianum-/>+TX、PlantShield/>+TX、/>+TX、Trianum-/>)+TX、哈茨木霉T-39+TX、非钩木霉(Trichoderma inhamatum)+TX、康宁木霉+TX、木霉属LC52/>+TX、木素木霉+TX、长柄木霉+TX、多孢木霉(Trichoderma polysporum)(Binab/>)+TX、紫杉木霉+TX、绿色木霉+TX、绿色木霉(原来称为绿色粘帚霉GL-21)+TX、绿色木霉+TX、绿色木霉菌株ICC 080/>+TX、茁芽丝孢酵母+TX、毛孢子菌属+TX、单端孢属+TX、粉红单端孢+TX、Typhula phacorrhiza菌株94670+TX、Typhula phacorrhiza菌株94671+TX、黑细基格孢+TX、奥德曼细基格孢(Ulocladium oudemansii)(Botry-/>)+TX、玉蜀黍黑粉菌+TX、各种细菌和补充营养素(Natural/>)+TX、各种真菌(Millennium/>)+TX、厚垣轮枝孢菌+TX、蜡蚧轮枝菌(/>+TX、/>)+TX、Vip3Aa20/>+TX、Virgibaclillusmarismortui+TX、野油菜黄单胞菌(Xanthomonas campestris pv.Poae)/>+TX、伯氏致病杆菌+TX、嗜线虫致病杆菌;以及
植物提取物,包括:松油+TX、印楝素(Plasma Neem/>+TX、+TX、/>+TX、Molt-/>+TX、植物IGR(/>+TX、)+TX、菜籽油(Lilly Miller/>)+TX、土荆芥附近荆芥(Chenopodiumambrosioides near ambrosioides)/>+TX、菊花浓汁(Chrysanthemumextract)/>+TX、提取印楝油(extract of neem oil)/>+TX、唇形科的精油/>+TX、丁香迷迭香薄荷的提取物和百里香精油(Garden insect)+TX、甜菜碱/>+TX、大蒜+TX、柠檬草精油/>+TX、印度楝树精油+TX、猫薄荷(薄荷精油)+TX、荆芥卡塔琳娜州(Nepeta catarina)+TX、尼古丁+Tx、牛至精油/>+TX、胡麻科精油/>+TX、除虫菊+TX、皂皮树/>+TX、大虎杖(Reynoutria sachalinensis)(/>+TX、)+TX、鱼藤酮(Eco/>)+TX、芸香料植物提取物/>+TX、豆油(Ortho/>)+TX、茶树精油(Timorex/>)+TX、百里香精油+TX、MMF+TX、/>+TX、迷迭香芝麻薄荷百里香和肉桂提取物的混合物(EF/>)+TX、丁香迷迭香和薄荷提取物的混合物(EF/>)+TX、丁香薄荷大蒜油和薄菏的混合物(Soil/>)+TX、高岭土/>+TX、储存葡萄糖的褐藻以及
信息素,包括:黑头火虫信息素(3M Sprayable Blackheaded FireWO rm)+TX、鳕鱼蛾信息素(Codling Moth Pheromone)(派拉蒙分配器(Paramount dispenser)-(CM)/Isomate C-/>)+TX、葡萄莓果蛾信息素(Grape BerryMoth Pheromone)(3M MEC-GBM Sprayable/>)+TX、稻纵卷叶螟性信息素(Leafroller pheromone)(3M MEC–LR Sprayable/>)+TX、家蝇信息素(Muscamone)(Snip7 Fly/>+TX、Starbar Premium Fly/>)+TX、东方水果蛾信息素(Oriental Fruit Moth Pheromone)(3M oriental fruit moth sprayable)+TX、桃树钻信息素(Peachtree Borer Pheromone)(Isomate-/>)+TX、番茄蛾类信息素(Tomato PinWO rm Pheromone)(3M Sprayable/>)+TX、衣透斯特粉末(Entostat powder)(从棕榈树提取)(Exosex/>)+TX、(E+TX、Z+TX、Z)-3+TX、8+TX、11醋酸十四酯+TX、(Z+TX,Z+TX,E)-7+TX、11+TX、13-十六碳三烯醛+TX、(E+TX,Z)-7+Tx、9-十二碳二烯-1-基乙酸酯+TX、2-甲基-1-丁醇+TX、乙酸钙+TX、/>+TX、/>+TX、Check-/>+TX、紫杉醇;以及
宏生物剂,包括:短距蚜小蜂+TX、阿尔蚜茧蜂(Aphidius ervi)(Aphelinus-)+TX、Acerophagus papaya+TX、二星瓢虫(Adalia-/>)+TX、二星瓢虫/>+TX、二星瓢虫/>+TX、串茧跳小蜂(Ageniaspis citricola)+TX、巢蛾多胚跳小蜂+TX、安氏钝绥螨(Amblyseius andersoni)(/>+TX、Andersoni-/>)+TX、加州钝绥螨(Amblyseius californicus)(/>+TX、/>)+TX、胡瓜钝绥螨(/>+TX、Bugline/>)+TX、伪钝绥螨+TX、斯氏钝绥螨(Bugline/>+TX、Swirskii-/>)+TX、奥氏钝绥螨(WO/>)+TX、粉虱细蜂(Amitus hesperidum)+TX、原缨翅缨小蜂(Anagrusatomus)+TX、暗腹长索跳小蜂(Anagyrus fusciventris)+TX、卡玛长索跳小蜂(Anagyruskamali)+TX、Anagyrus loecki+TX、粉蚧长索跳小蜂(Anagyrus pseudococci)+TX、红蜡蚧扁角跳小蜂(Anicetus benefices)+TX、金小蜂(Anisopteromalus calandrae)+TX、林地花蝽(Anthocoris nemoralis)(Anthocoris-)+TX、短距蚜小蜂(/>+TX、/>)+TX、短翅蚜小蜂(Aphelinus asychis)+TX、科列马·阿布拉小蜂(Aphidius colemani)/>+TX、阿尔蚜茧蜂/>+TX、烟蚜茧蜂+TX、桃赤蚜蚜茧蜂(Aphipar-/>)+TX、食蚜瘿蚊/>+TX、食蚜瘿蚊/>+TX、岭南蚜小蜂+TX、印巴黄金蚜小蜂+TX、蠊卵长尾啮小蜂(Aprostocetus hagenowii)+TX、隐翅虫(Atheta coriaria)+TX、熊蜂属+TX、欧洲熊蜂(Natupol/>)+TX、欧洲熊蜂(+TX、/>)+TX、Cephalonomia stephanoderis+TX、黑背红瓢虫(Chilocorus nigritus)+TX、普通草蛉(Chrysoperla carnea)/>+TX、普通草蛉/>+TX、红通草蛉(Chrysoperla rufilabris)+TX、Cirrospilusingenuus+TX、Cirrospilus quadristriatus+TX、白星橘啮小蜂(Citrostichusphyllocnistoides)+TX、Closterocerus chamaeleon+TX、Closterocerus属+TX、Coccidoxenoides perminutus/>+TX、Coccophagus cowperi+TX、赖食蚧蚜小蜂(Coccophagus lycimnia)+TX、螟黄足盘绒茧蜂+TX、菜蛾盘绒茧蜂+TX、孟氏隐唇瓢虫(+TX、/>)+TX、日本方头甲+TX、西伯利亚离颚茧蜂+TX、西伯利亚离颚茧蜂/>+TX、豌豆潜蝇姬小蜂/>+TX、小黑瓢虫(Delphastus catalinae)/>+TX、Delphastus pusillus+TX、Diachasmimorpha krausii+TX、长尾潜蝇茧蜂+TX、Diaparsis jucunda+TX、阿里食虱跳小蜂(Diaphorencyrtus aligarhensis)+TX、豌豆潜叶蝇姬小蜂+TX、豌豆潜叶蝇姬小蜂(+TX、/>)+TX、西伯利亚离颚茧蜂(/>+TX、)+TX、歧脉跳小蜂属+TX、盾蚧长缨蚜小蜂+TX、丽蚜小蜂(Encarsia/>+TX、+TX、En-/>)+TX、浆角蚜小蜂(Eretmocerus eremicus)+TX、哥德恩蚜小蜂(Encarsia guadeloupae)+TX、海地恩蚜小蜂(Encarsiahaitiensis)+TX、细扁食蚜蝇/>+TX、Eretmoceris siphonini+TX、浆角蚜小蜂(Eretmocerus californicus)+TX、浆角蚜小蜂(Eretmocerus eremicus)(/>+TX、Eretline/>)+TX、浆角蚜小蜂(Eretmocerus eremicus)/>+TX、海氏桨角蚜小蜂+TX、蒙氏桨角蚜小蜂(/>+TX、Eretline/>)+TX、Eretmocerussiphonini+TX、四斑光缘瓢虫(Exochomus quadripustulatus)+TX、食螨瘿蚊(Feltiellaacarisuga)/>+TX、食螨瘿蚊/>+TX、阿里山潜蝇茧蜂+TX、Fopius ceratitivorus+TX、芒柄花黄素(Wirless/>)+TX、细腰凶蓟马+TX、西方静走螨(Galendromus occidentalis)+TX、莱氏棱角肿腿蜂(Goniozus legneri)+TX、麦蛾柔茧蜂+TX、异色瓢虫/>+TX、异小杆线虫属(Lawn/>)+TX、嗜菌异小杆线虫(NemaShield/>+TX、/>+TX、Terranem-/>+TX、/>+TX、/>+TX、B-/>+TX、+TX、/>)+TX、大异小杆线虫(Heterorhabditis megidis)(Nemasys/>+TX、BioNem/>+TX、Exhibitline/>+TX、Larvanem-/>)+TX、集栖瓢虫(Hippodamia convergens)+TX、尖狭下盾螨(Hypoaspis aculeifer)(Aculeifer-+TX、Entomite-/>)+TX、兵下盾螨(Hypoaspis miles)(Hypoline/>+TX、Entomite-/>)+TX、黑色枝跗瘿蜂+TX、Lecanoideus floccissimus+TX、Lemophaguserrabundus+TX、三色丽突跳小蜂(Leptomastidea abnormis)+TX、Leptomastixdactylopii/>+TX、长角跳小蜂(Leptomastix epona)+TX、Lindoruslophanthae+TX、Lipolexis oregmae+TX、叉叶绿蝇/>+TX、茶足柄瘤蚜茧蜂+TX、暗黑长脊盲蝽(Macrolophus caliginosus)(Mirical-/>+TX、Macroline/>+TX、)+TX、Mesoseiulus longipes+TX、黄色阔柄跳小蜂(Metaphycus flavus)+TX、Metaphycus lounsburyi+TX、角纹脉褐蛉/>+TX、黄色花翅跳小蜂(Microterys flavus)+TX、Muscidifurax raptorellus和Spalangia cameroni+TX、Neodryinus typhlocybae+TX、加州新小绥螨+TX、胡瓜钝绥螨+TX、虚伪新小绥螨(Neoseiulus fallacis)+TX、Nesideocoris tenuis(/>+TX、/>)+TX、古铜黑蝇/>+TX、狡小花蝽(Oriusinsidiosus)(Thripor-/>+TX、Oriline/>)+TX、无毛小花蝽(Orius laevigatus)(Thripor-/>+TX、Oriline/>)+TX、大型小花蝽(Orius majusculus)(Oriline/>)+TX、小黑花椿象(Thripor-/>)+TX、Pauesia juniperorum+TX、酸酱瓢虫腹柄姬小蜂(Pediobius foveolatus)+TX、Phasmarhabditis hermaphrodita/>+TX、Phymastichus coffea+TX、Phytoseiulus macropilus+TX、智利小植绥螨(/>+TX、Phytoline/>)+TX、斑腹刺益蝽/>+TX、Pseudacteon curvatus+TX、Pseudacteon obtusus+TX、Pseudacteon tricuspis+TX、Pseudaphycus maculipennis+TX、Pseudleptomastix mexicana+TX、具毛嗜木虱跳小蜂(Psyllaephagus pilosus)+TX、同色短背茧蜂(Psyttalia concolor)(络合物)+TX、胯姬小蜂属+TX、Rhyzobius lophanthae+TX、澳洲瓢虫+TX、Rumina decollate+TX、Semielacher petiolatus+TX、麦长管蚜+TX、小卷蛾斯氏线虫(Nematac/>+TX、/>+TX、BioNem/>+TX、/>+TX、/>+TX、/>)+TX、夜蛾斯氏线虫(+TX、Nemasys/>+TX、BioNem/>+TX、Steinernema-/>+TX、+TX、/>+TX、Exhibitline/>+TX、Scia-/>+TX、)+TX、锯蜂线虫(Steinernema kraussei)(Nemasys/>+TX、BioNem/>+TX、Exhibitline/>)+TX、里奥布拉夫线虫(Steinernema riobrave)(/>+TX、/>)+TX、蝼蛄斯氏线虫(Steinernema scapterisci)(Nematac/>)+TX、斯氏线虫属+TX、Steinernematid属(Guardian/>)+TX、深点食螨瓢虫+TX、亮腹釉小蜂+TX、Tetrastichus setifer+TX、Thripobiussemiluteus+TX、中华长尾小蜂(Torymus sinensis)+TX、甘蓝夜蛾赤眼蜂(Tricholine/>)+TX、甘蓝夜蛾赤眼蜂(Tricho-/>)+TX、广赤眼蜂+TX、微小赤眼蜂+TX、玉米螟赤眼蜂+TX、宽脉赤眼蜂(Trichogramma platneri)+TX、短管赤眼蜂+TX、螟黑点瘤姬蜂;以及
其他生物剂,包括:脱落酸+TX、+TX、银叶菌(Chondrostereumpurpureum)(Chontrol/>)+TX、盘长孢状刺盘孢/>+TX、辛酸铜盐+TX、δ陷阱(Delta trap)(Trapline/>)+TX、解淀粉欧文氏菌(Harpin)(+TX、Ni-HIBIT Gold/>)+TX、磷酸高铁/>+TX、漏斗陷阱(Trapline/>)+TX、/>+TX、Grower's/>+TX、高油菜素内酯+TX、磷酸铁(Lilly Miller WO rry Free Ferramol Slug&Snail/>)+TX、MCP冰雹陷阱(Trapline)+TX、Microctonus hyperodae+TX、Mycoleptodiscus terrestris(Des-/>)+TX、+TX、/>+TX、/>+TX、信息素陷阱(Thripline/>)+TX、碳酸氢钾/>+TX、脂肪酸的钾盐/>+TX、硅酸钾溶液(Sil-)+TX、碘化钾+硫氰酸钾/>+TX、SuffOil-/>+TX、蜘蛛毒+TX、蝗虫微孢子虫(Semaspore Organic Grasshopper/>)+TX、粘着陷阱(Trapline/>+TX、Rebell/>)+TX以及陷阱(Takitrapline y+/>)+TX
或选自以下的生物活性化合物或试剂:溴氟菊酯+TX、氟螨嗪(Diflovidazine)+TX、Flometoquin+TX、Fluhexafon+TX、小菜蛾颗粒体病毒+TX、苹果蠹蛾颗粒体病毒+TX、新烟磷(Imicyafos)+TX、烟芽夜蛾核多角体病毒+TX、Heliothis punctigera核多角体病毒+TX、玉米穗夜蛾核多角体病毒+TX、草地贪夜蛾核多角体病毒+TX、小菜蛾核多角体病毒+TX、对伞花烃+TX、Pyflubumide+TX、Pyrafluprole+TX、QRD 420+TX、QRD 452+TX、QRD 460+TX、萜类混合物+TX、萜类+TX、氟氰虫酰胺(Tetraniliprole)+TX和α-萜品烯+TX;
或由代码+TX提及的活性物质,如代码AE 1887196(BSC-BX60309)+TX、代码NNI-0745GR+TX、代码IKI-3106+TX、代码JT-L001+TX、代码ZNQ-08056+TX、代码IPPA152201+TX、代码HNPC-A9908(CAS:[660411-21-2])+TX、代码HNPC-A2005(CAS:[860028-12-2])+TX、代码JS118+TX、代码ZJ0967+TX、代码ZJ2242+TX、代码JS7119(CAS:[929545-74-4])+TX、代码SN-1172+TX、代码HNPC-A9835+TX、代码HNPC-A9955+TX、代码HNPC-A3061+TX、代码Chuanhua89-1+TX、代码IPP-10+TX、代码ZJ3265+TX、代码JS9117+TX、代码ZJ3757+TX、代码ZJ4042+TX、代码ZJ4014+TX、代码ITM-121+TX、代码DPX-RAB55(DKI-2301)+TX、代码NA-89+TX、代码MIE-1209+TX、代码MCI-8007+TX、代码BCS-CL73507+TX、代码S-1871+TX、代码DPX-RDS63+TX、代码AKD-1193+TX。
在活性成分之后的括号中的参考例如[3878-19-1]是指化学文摘登记号。以上描述的混合配对物是已知的。当活性成分包括在“The Pesticide Manual[杀有害生物剂手册]”[The Pesticide Manual-A WO rld Compendium[杀有害生物剂手册-全球概览];第13版;编者:C.D.S.TomLin;英国农作物保护委员会(The British Crop ProtectionCouncil)]中时,它们在上文对于特定化合物在圆括号内给定的条目编号之下描述于该手册中;例如,化合物“阿维菌素”在条目编号(1)之下描述。其中“[CCN]”是对于上文的特定化合物来加上的,所述的化合物包括在“Compendium of Pesticide Common Names”(农药通用名概要)中,它们可以在国际互联网[A.WO od;Compendium of Pesticide Common Names,Copyright1995-2004]中查到;例如,化合物“乙酰虫腈”描述于国际互联网地址http://www.alanWOod.net/pesticides/acetoprole.html。
上述的活性成分中大部分在上文是通过所谓的“通用名”、相关的“ISO通用名”或在个别情况下使用的另一个“通用名”来提及。若其名称不是“通用名”,则所使用的名称种类以特定化合物的圓括号中所给出的名称来代替;在该情形下,使用IUPAC名称、IUPAC/化学文摘名、“化学名称”、“传统名称”、“化合物名”或“研究代码”,或若既不使用指定名称也不使用“通用名”,则使用别名。“CAS登记号”意指化学文摘登记号。
选自表1-4的具有式I的化合物与上述活性成分的活性成分混合物包括选自表1-4的化合物和上述活性成分,优选地是处于从100:1至1:6000的混合比率,尤其是从50:1至1:50,更尤其是处于从20:1至1:20的比率,甚至更尤其从10:1至1:10,非常尤其是从5:1和1:5,尤其优选的是从2:1至1:2的比率给出的,并且从4:1至2:1的比率同样是优选的,特别是处于1:1,或5:1,或5:2,或5:3,或5:4,或4:1,或4:2,或4:3,或3:1,或3:2,或2:1,或1:5,或2:5,或3:5,或4:5,或1:4,或2:4,或3:4,或1:3,或2:3,或1:2,或1:600,或1:300,或1:150,或1:35,或2:35,或4:35,或1:75,或2:75,或4:75,或1:6000,或1:3000,或1:1500,或1:350,或2:350,或4:350,或1:750,或2:750,或4:750的比率。那些混合比率是按重量计的。
如上描述的混合物可以被用于控制有害生物的方法中,该方法包括将含如上描述的混合物的组合物施用于有害生物或其环境中,除了通过手术或疗法用于处理人或动物体的方法以及在人或动物体上实施的诊断方法之外。
包含选自表1-4的具有式I的化合物以及一种或多种如上所述的活性成分的混合物可以例如以一种单一的“掺水即用”的形式施用,以组合的喷洒混合物(该混合物由这些单一活性成分的单独配制品构成)(例如一种“桶混制剂”)施用,并且当以一种顺序的方式(即,一个在另一个适度短的时期之后,例如几小时或几天)施用时组合使用这些单独活性成分来施用。施用选自表1-4的具有式I的化合物和上述活性成分的顺序对于实施本发明并不是至关重要的。
根据本发明的组合物还可以包含其他固体或液体助剂,如稳定剂,例如未环氧化的或环氧化的植物油(例如环氧化的椰子油、菜籽油或大豆油),消泡剂(例如硅酮油),防腐剂,粘度调节剂,粘合剂和/或增粘剂,肥料或其他用于获得特定效果的活性成分,例如杀细菌剂、杀真菌剂、杀线虫剂、植物活化剂、杀软体动物剂或除草剂。
根据本发明的组合物是以本身已知的方式,在不存在助剂的情况下,例如通过研磨、筛选和/或压缩固体活性成分;和在至少一种助剂的存在下,例如通过紧密混合活性成分与一种或多种助剂和/或将活性成分与一种或多种助剂一起研磨来制备。用于制备组合物的这些方法和用于制备这些组合物的化合物I的用途也是本发明的主题。
这些组合物的施用方法,即是控制上述类型的有害生物的方法,如喷雾、雾化,撒粉,刷涂,包衣,撒播或浇灌-它们被选择以适于普遍情况的预期目的-并且这些组合物用于控制上述类型的有害生物的用途是本发明的其他主题。典型的浓度比是在0.1与1000ppm之间,优选在0.1与500ppm之间的活性成分。每公项的施用量总体上是每公项1g到2000g活性成分,尤其是10g/ha到1000g/ha,优选地10g/ha到600g/ha。
在作物保护领域中,优选的施用方法是施用至这些植物的叶(叶施药),可能的是选择施用的频率和比率以符合所讨论的有害生物的侵染风险。可替代地,该活性成分可以通过根系统(内吸作用)到达植物,这是通过用一种液体组合物将这些植物的所在地浸透或者通过将固体形式的活性成分引入植物的所在地(例如引入土壤,例如以颗粒(土施)的形式)来实现的。在水稻作物的情况下,这样的颗粒剂可以被计量地添加淹水的稻田中。
本发明的这些化合物及其组合物还适合于植物繁殖材料的保护(例如种子,像果实、块茎或籽粒,或者苗圃植物)对抗上述类型的有害生物。可以用该化合物在种植前对该繁殖材料进行处理,例如可以在播种前对种子进行处理。可替代地,该化合物可以施用至种子籽粒(包衣),这是通过将籽粒浸渍入液体组合物中或通过施涂一种固体组合物层实现的。当该繁殖材料被种植在施用处时,还可能例如在条播期间将这些组合物施入种子犁沟。这些用于植物繁殖材料的处理方法和因此处理的植物繁殖材料是本发明另外的主题。典型的处理比率将取决于有待控制的植物以及有害生物/真菌,通常在每100kg种子1克至200克之间,优选在每100kg种子5克至150克之间,例如在每100kg种子10克至100克之间。
术语种子包括所有种类的种子以及植物繁殖体,包括但并不限于真正的种子、种子块、吸盘、谷粒、鳞球茎、果实、块茎、谷物、根茎、插条、切割枝条以及类似物并且在一个优选的实施例中是指真正的种子。
本发明还包括用具有式I的化合物包衣或处理的种子或含有具有式I的化合物的种子。尽管成分的更多或更少的部分可以渗透到该种子材料中,这取决于施用的方法,术语“包衣或处理和/或含有”通常表示在施用的时候,在大多数情况下,该活性成分在该种子的表面。当所述种子产物(再)种植时,它可以吸收该活性成分。在一个实施例中,本发明使得一种其上粘附有具有式(I)的化合物的植物繁殖材料可得。此外,由此可得一种包括用具有式(I)的化合物处理过的植物繁殖材料的组合物。
种子处理包括本领域中已知的所有适合的种子处理技术,例如拌种、种子包衣、种子撒粉、浸种以及种子造粒。可以通过任何已知的方法实现具有式I的化合物的种子处理施用,例如,在这些种子播种之前或播种/种植过程中喷雾或通过撒粉。
生物学实例:
接下来的实例用来阐明本发明:本发明的某些化合物与已知的化合物的区别可以在于在低施用率下更大的疗效,这可以由本领域的普通技术人员使用在实例中概述的实验程序,使用更低的施用率(如果必要的话)例如,50ppm、25ppm、12.5ppm、6ppm、3ppm、1.5ppm、0.8ppm、0.2ppm或0.05ppm来证实。
实例B1:海灰翅夜蛾(埃及棉叶虫)
将棉花叶圆片置于24孔微量滴定板中的琼脂上并且用从10’000ppm DMSO储备溶液中制备的水性测试溶液进行喷雾。在干燥之后,将叶圆片用五只L1期幼虫进行侵染。侵染3天之后,相比于未处理样品,针对死亡率、拒食效果以及生长抑制对这些样品进行评估。当类别(死亡率、拒食效果、以及生长抑制)中至少一个高于未处理样品时,测试样品对海灰翅夜蛾给出了控制。
以下化合物在200ppm施用率下得到至少80%的控制:P2、P5。
实例B2:海灰翅夜蛾(埃及棉叶虫)
将测试化合物用移液管从10’000ppm DMSO储备溶液施用到24孔板中并且与琼脂进行混合。将莴苣种子置于琼脂上并且用另一块也包含琼脂的平板封闭该多孔板。7天之后,根吸收了化合物并且莴苣生长进入了盖平板。然后,将这些莴苣叶切到盖平板中。将夜蛾属卵吸移穿过潮湿凝胶印记纸上的塑料模板及其所封闭的盖平板。侵染6天之后,相比于未处理样品,针对死亡率、拒食效果以及生长抑制对这些样品进行评估。
以下化合物在12.5ppm测试比率下给出了三个类别(死亡率、拒食效果、或生长抑制)中至少一个的至少80%的效果:P2
实例B3:小菜蛾(Plutella xylostella)(小菜蛾(Diamond back moth))
将具有人工饲料的24孔微量滴定板用从10’000ppm DMSO储备溶液中制备的水性测试溶液通过移液进行处理。在干燥之后,用L2期幼虫对各板进行侵染(10至15只/孔)。侵染5天之后,相比于未处理样品,针对死亡率和生长抑制对这些样品进行评估。
以下化合物在200ppm施用率处给出了这两个类别(死亡率或生长抑制)中至少一个的至少80%的效果:P2、P3、P4、P5、P9、P10、P12和P17。
实例B4:黄瓜条叶甲(玉米根虫)
将24孔微量滴定板中的置于琼脂层上的玉米芽用通过喷雾用从10’000ppm DMSO储备溶液中制备的水性测试溶液进行处理。在干燥之后,用L2期幼虫对各板进行侵染(6至10只/孔)。侵染4天之后,相比于未处理样品,针对死亡率和生长抑制对这些样品进行评估。
以下化合物在200ppm施用率处给出了这两个类别(死亡率或生长抑制)中至少一个的至少80%的效果:P2、P3、P4、P5、P6、P10、P11、P12、P15、P16和P17。
实例B5:桃蚜(碧桃蚜)
将向日葵叶圆片置于24孔微量滴定板中的琼脂上并且用从10’000ppm DMSO储备溶液中制备的水性测试溶液进行喷雾。在干燥之后,将这些叶圆片用混合年龄的蚜虫群体进行侵染。侵染6天之后,针对死亡率对这些样品进行评估。
以下化合物在200ppm施用率下产生至少80%死亡率:P2、P4、P5、P10、P12、P15和P17。
实例B6:桃蚜(碧桃蚜)
将受到混合年龄的蚜虫群体侵染的豌豆幼苗的根部直接放在从10'000ppm DMSO储备溶液中制备的水性测试溶液中。将幼苗放置在测试溶液中6天之后,针对死亡率对这些样品进行评估。
以下化合物在24ppm测试比率下产生至少80%死亡率:P2、P5、P6、P10、P12、P15、P17和P19。
实例B7:烟粉虱(棉粉虱)
将棉花叶圆片置于24孔微量滴定板中的琼脂上并且用从10'000ppm DMSO储备溶液中制备的水性测试溶液进行喷雾。在干燥之后,将叶圆片用成年粉虱进行侵染。孵育6天之后,针对死亡率对这些样品进行检查。
以下化合物在200ppm施用率下产生至少80%死亡率:P2、P5、P11、P12和P17。
实例B8:大豆褐椿(Euschistus heros)(新热带褐臭蝽)
将24孔微量滴定板中的琼脂上的大豆叶片用从10’000ppm DMSO储备溶液中制备的水性测试溶液进行喷雾。在干燥之后,用N2期若虫对叶片进行侵染。侵染5天之后,相比于未处理样品,针对死亡率和生长抑制对这些样品进行评估。
以下化合物在200ppm施用率处给出了这两个类别(死亡率或生长抑制)中至少一个的至少80%的效果:P2、P5、P6、P9、P11、P12、P13、P15、P16、P17和P19。
实例B10:二点叶螨(二斑叶螨)
将24孔微量滴定板中的琼脂上的豆叶圆片用从10’000ppm DMSO储备溶液中制备的水性测试溶液进行喷雾。在干燥之后,将这些叶圆片用一个混合年龄的螨种群侵染。侵染8天之后,针对混合种群(流动平台)的死亡率对这些样品进行评估。
实例B11:烟蓟马(葱蓟马)
将向日葵叶圆片置于24孔微量滴定板中的琼脂上并且用从10'000ppm DMSO储备溶液中制备的水性测试溶液进行喷雾。在干燥之后,将这些叶圆片用混合年龄的蓟马群侵染。侵染6天之后,针对死亡率对这些样品进行评估。
实例B12:西花蓟马(西方花蓟马)
将向日葵叶圆片置于24孔微量滴定板中的琼脂上并且用从10’000DMSO储备溶液中制备的水性测试溶液进行喷雾。在干燥之后,将叶圆片用混合年龄的花蓟马种群进行侵染。侵染7天之后,针对死亡率对这些样品进行评估。
实例B13:根据本发明的化合物P17与现有技术中结构最接近的化合物的杀昆虫活
性的比较
表B13中总结了根据本发明的化合物P17和从WO 2016/026848的化合物P15对抗大豆褐椿的活性。
表B13:
测试说明:
用稀释的测试水溶液喷雾2周龄大豆植物。之后,植物被10只臭蝽若虫(N2)侵染。将大豆种子作为另外的食物来源添加到测试系统中。在处理5天之后,针对死亡率对样品进行评估。
Claims (15)
1.一种具有式(I)的化合物,
其中
A是CH或N;
X是S、SO或SO2;
R1是C1-C4烷基、C1-C4卤代烷基或C3-C6环烷基-C1-C4烷基;
G1是N或CH;
X1是O、S或NR3;其中R3是氢或C1-C4烷基;
R2是卤素、C1-C6卤代烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基或C1-C6卤代烷氧基;
R7是氢、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基;以及
R8是卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基;以及具有式I的化合物的农用化学上可接受的盐、立体异构体、对映异构体、互变异构体和N-氧化物。
2.根据权利要求1所述的化合物,或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R1是C1-C4烷基或C3-C6环烷基-C1-C4烷基。
3.根据权利要求1或权利要求2所述的化合物,或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R2是卤素、C1-C4卤代烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基。
4.根据权利要求1、2或3中任一项所述的化合物,或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R7是氢、氟、氰基、C1-C4烷氧基羰基、C1-C4烷基。
5.根据权利要求1、2、3或4中任一项所述的化合物,或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R8是氰基、氟或C1-C4烷基。
6.根据权利要求1、2、3、4或5中任一项所述的化合物,或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中X1是NR3,其中R3是C1-C4烷基。
7.根据权利要求1、2、3、4、5或6中任一项所述的化合物,或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中X是S或SO2。
8.根据权利要求1、2、3、4、5、6或7中任一项所述的化合物,或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R1是C1-C4烷基或环丙基甲基,并且R2是卤素或C1-C3卤代烷基。
9.根据权利要求1、2、3、4、5、6、7或8中任一项所述的化合物,或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中R7是氢、甲基、乙基或氟,并且R8是氟、甲基或乙基。
10.根据权利要求1所述的化合物,或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中
A是CH或N;
X是S或SO2;
G1是N或CH;
X1是NCH3;
R1是甲基、乙基、正丙基、异丙基或环丙基甲基;
R2是C1-C2卤代烷基;
R7是甲基或氟;以及
R8是氟、甲基或乙基。
11.根据权利要求1、2、3、4、5、6、7、8、9或10中任一项所述的化合物,或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中A是N。
12.一种具有式IX的化合物,
其中
A是CH或N,优选N;
X是S、SO或SO2,优选地是S或SO2;
R1是C1-C4烷基,优选乙基;
G1是N或CH;
R3是氢或C1-C4烷基,优选地是甲基;
R2是卤素、C1-C6卤代烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基或C1-C6卤代烷氧基;优选地是CF3;
R7是氢、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基,优选地,R7是甲基或氟;以及
R8是卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基,优选地,R8是甲基或氟;或其位置异构体,或其异构混合物;或
一种具有式XI的化合物,
其中
A是CH或N,优选N;
X是S、SO或SO2,优选地是S或SO2;
R1是C1-C4烷基,优选乙基;
R7是氢、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基,优选地,R7是甲基或氟;以及
R8是卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基,优选地,R8是甲基或氟;或
一种具有式XII的化合物,
其中
A是CH或N,优选N;
X是S、SO或SO2,优选地是S或SO2;
R1是C1-C4烷基,优选乙基;
R7是氢、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基,优选地,R7是甲基或氟;
R8是卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基,优选地,R8是甲基或氟;或
一种具有式XIII的化合物,
其中
A是CH或N,优选N;
X是S、SO或SO2,优选地是S或SO2;
R1是C1-C4烷基,优选乙基;
R7是氢、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基,优选地,R7是甲基或氟;
R8是卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基硫烷基-C1-C4烷基、C1-C4烷基亚磺酰基-C1-C4烷基、C1-C4烷基磺酰基-C1-C4烷基或C1-C4烷基氧基羰基,优选地,R8是甲基或氟;以及
RLG是C1-C4烷基,优选地是甲基或乙基;或
一种具有式XVI的化合物,
其中
A是CH或N,优选N;
X是S、SO或SO2,优选地是S或SO2;
R1是C1-C4烷基,优选乙基;
R11是C1-C4烷基,优选地是甲基或乙基;以及
RLG是C1-C4烷基,优选地是甲基或乙基。
13.一种组合物,该组合物包含杀昆虫、杀螨、杀线虫、或杀软体动物有效量的如权利要求1-12中任一项所定义的具有式(I)的化合物,或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,以及任选地,助剂或稀释剂。
14.一种对抗并控制昆虫、螨、线虫或软体动物的方法,该方法包括向有害生物、有害生物的场所或易受有害生物攻击的植物施用杀昆虫、杀螨、杀线虫、或杀软体动物有效量的如权利要求1-12中任一项所定义的具有式(I)的化合物,或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,或如权利要求13所定义的组合物。
15.一种用于保护植物繁殖材料免受昆虫、螨、线虫或软体动物攻击的方法,该方法包括用根据权利要求13所述的组合物处理该繁殖材料或该繁殖材料所种植的场所。
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WO2022017975A1 (en) | 2020-07-18 | 2022-01-27 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
CN116234811A (zh) | 2020-09-02 | 2023-06-06 | 先正达农作物保护股份公司 | 具有含硫取代基的杀有害生物活性的杂环衍生物 |
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WO2024121335A1 (en) | 2022-12-07 | 2024-06-13 | Syngenta Crop Protection Ag | Synthesis of sulfoximine compounds having a stereogenic sulfur atom |
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Also Published As
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TWI793104B (zh) | 2023-02-21 |
RU2019128920A (ru) | 2021-03-23 |
CN110312707B (zh) | 2023-06-23 |
CA3053985A1 (en) | 2018-08-30 |
US20190367514A1 (en) | 2019-12-05 |
KR102600081B1 (ko) | 2023-11-07 |
UA126150C2 (uk) | 2022-08-25 |
MX2019009937A (es) | 2019-10-09 |
BR112019017382B1 (pt) | 2023-02-23 |
EP3585770B1 (en) | 2022-03-23 |
KR20190120269A (ko) | 2019-10-23 |
MX2022014118A (es) | 2022-12-08 |
UY37609A (es) | 2018-09-28 |
RU2019128920A3 (zh) | 2021-03-23 |
JP7053644B2 (ja) | 2022-04-12 |
EP3585770A1 (en) | 2020-01-01 |
JP2020508312A (ja) | 2020-03-19 |
CO2019009005A2 (es) | 2019-08-30 |
US11440910B2 (en) | 2022-09-13 |
CN110312707A (zh) | 2019-10-08 |
TW201841912A (zh) | 2018-12-01 |
PH12019501899A1 (en) | 2019-10-21 |
ES2920275T3 (es) | 2022-08-02 |
WO2018153778A1 (en) | 2018-08-30 |
AR110992A1 (es) | 2019-05-22 |
BR112019017382A2 (pt) | 2020-03-31 |
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