CN106661023B - 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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- CN106661023B CN106661023B CN201580042339.0A CN201580042339A CN106661023B CN 106661023 B CN106661023 B CN 106661023B CN 201580042339 A CN201580042339 A CN 201580042339A CN 106661023 B CN106661023 B CN 106661023B
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- alkyl
- halogenated
- halogen
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- compound
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- 125000001424 substituent group Chemical group 0.000 title claims abstract description 50
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 title description 6
- 239000011593 sulfur Substances 0.000 title description 4
- 229910052717 sulfur Inorganic materials 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 212
- 238000000034 method Methods 0.000 claims abstract description 66
- 150000003839 salts Chemical class 0.000 claims abstract description 40
- 239000003905 agrochemical Substances 0.000 claims abstract description 9
- -1 methoxyl group Chemical group 0.000 claims description 175
- 229910052736 halogen Inorganic materials 0.000 claims description 118
- 150000002367 halogens Chemical class 0.000 claims description 111
- 125000000217 alkyl group Chemical group 0.000 claims description 99
- 239000000203 mixture Substances 0.000 claims description 96
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 87
- 239000001257 hydrogen Substances 0.000 claims description 83
- 229910052739 hydrogen Inorganic materials 0.000 claims description 83
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 82
- 239000000463 material Substances 0.000 claims description 38
- 239000000470 constituent Substances 0.000 claims description 27
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 23
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 15
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 15
- 239000005864 Sulphur Substances 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
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- 241001465754 Metazoa Species 0.000 claims description 11
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- 238000006467 substitution reaction Methods 0.000 claims description 11
- 150000004820 halides Chemical class 0.000 claims description 10
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 230000008859 change Effects 0.000 claims description 6
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- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims 5
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 2
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims 1
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 238000002405 diagnostic procedure Methods 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 239000002917 insecticide Substances 0.000 abstract description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 162
- 239000002585 base Substances 0.000 description 105
- 239000000126 substance Substances 0.000 description 92
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 54
- 238000006243 chemical reaction Methods 0.000 description 53
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 45
- 241000196324 Embryophyta Species 0.000 description 44
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 44
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- 231100000765 toxin Toxicity 0.000 description 38
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 31
- 239000002904 solvent Substances 0.000 description 30
- 238000002360 preparation method Methods 0.000 description 28
- 239000000243 solution Substances 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 241000238631 Hexapoda Species 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
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- 235000002017 Zea mays subsp mays Nutrition 0.000 description 23
- 125000004414 alkyl thio group Chemical group 0.000 description 23
- 238000011160 research Methods 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 239000003795 chemical substances by application Substances 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 21
- 235000005822 corn Nutrition 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 20
- 229910052794 bromium Inorganic materials 0.000 description 20
- 229910052799 carbon Inorganic materials 0.000 description 20
- 239000000460 chlorine Substances 0.000 description 20
- 235000019441 ethanol Nutrition 0.000 description 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 19
- 239000003513 alkali Substances 0.000 description 19
- 229910052801 chlorine Inorganic materials 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 17
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 17
- 241000196508 Turbatrix Species 0.000 description 17
- 239000002671 adjuvant Substances 0.000 description 17
- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 17
- 229910052698 phosphorus Inorganic materials 0.000 description 17
- 239000011574 phosphorus Substances 0.000 description 17
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 15
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 15
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 14
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- 239000002023 wood Substances 0.000 description 13
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 13
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Abstract
具有化学式I的化合物
Description
本发明涉及包含硫取代基的杀有害生物活性(特别是杀虫活性)杂环衍生物,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(包括节肢动物并且特别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、WO 2013/191112和WO 2013/191113。
现在已经发现具有含硫的苯基和吡啶基取代基的杀有害生物活性杂环衍生物。
本发明因此涉及具有化学式I的化合物,
其中
A是CH、N或CR7;其中R7是C1-C4烷基、C1-C4卤代烷基、氰基、硝基或卤素;
X是S、SO或SO2;
R1是C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C3-C6环烷基-C1-C4烷基、被选自下组的取代基单或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基、C1-C4卤代烷基和C1-C4烷基;或
R1是被选自下组的取代基单或多取代的C3-C6环烷基-C1-C4烷基,该组由以下各项组成:卤素、氰基、C1-C4卤代烷基和C1-C4烷基;或
R1是C2-C6烯基、C2-C6卤代烯基或C2-C6炔基;
R2a和R2b彼此独立地是氢、卤素、氰基、C1-C6卤代烷基或被一个或两个选自下组的取代基取代的C1-C6卤代烷基,该组由以下各项组成:羟基、甲氧基和氰基;或
R2a和R2b彼此独立地是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、C1-C4卤代烷氧基、或–C(O)(C1-C4卤代烷基);或R2a和R2b彼此独立地是可以被选自下组的取代基单或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基、C1-C4卤代烷基和C1-C4烷基;
R3是氢、卤素、氰基、硝基、C1-C6烷基、C1-C6烷氧基、C1-C4烷氧基C1-C4烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6环烷基-C1-C4烷基,或
R3是被选自下组的取代基单或双取代的C3-C6环烷基,该组由以下各项组成:卤素、C1-C4烷基、C1-C4卤代烷基和氰基;或
R3是C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基;或
R3是可以被选自下组的取代基单或多取代的苯基,该组由以下各项组成:卤素、氰基、硝基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷氧基C1-C4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、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、和-C(O)C1-C4卤代烷基;或
R3是C1-C6卤代烷基硫烷基、C1-C6卤代烷基亚磺酰基、C1-C6卤代烷基磺酰基、C1-C6卤代烷氧基、-C(O)C1-C4卤代烷基、C1-C6烷基硫烷基、C1-C6烷基亚磺酰基、或C1-C6烷基磺酰基;或
R3是可以被选自下组的取代基单或多取代的嘧啶基,该组由以下各项组成:卤素、氰基、硝基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷氧基C1-C4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、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基和-C(O)C1-C4卤代烷基;或
R3是可以被选自下组的取代基单或多取代的吡啶基,该组由以下各项组成:卤素、氰基、硝基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷氧基C1-C4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、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、或C1-C4烷基磺酰基和-C(O)C1-C4卤代烷基;或
R3是部分饱和或完全饱和的五元至六元芳香族环系统,该环系统经由氮原子连接至包含取代基G3的环,所述环系统可以被选自下组的取代基单或多取代,该组由以下各项组成:卤素、氰基、硝基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷氧基C1-C4烷基、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、-C(O)C1-C4烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;所述环系统包含选自下组的1个、2个或3个杂原子,该组由以下各项组成:氮、氧和硫;其中所述环系统可以不包含多于一个氧原子和不多于一个硫原子;
R6是氢、C1-C4烷基、C1-C4卤代烷基、卤素或氰基;
G1是CR4,其中R4是氢、C1-C4烷基、C1-C4卤代烷基、氰基或卤素;
G2是N或CR5,其中R5是氢、C1-C4烷基、C1-C4卤代烷基、氰基、硝基或卤素;
G3是N或CR8,其中R8是氢、C1-C4烷基、C1-C4卤代烷基、卤素或氰基;以及具有化学式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化学式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,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,如未经取代的或像被卤素取代的C1-C4烷羧酸(例如乙酸),如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),如羟基羧酸(例如抗坏血酸、乳酸、苹果酸、酒石酸或柠檬酸),或如苯甲酸;或有机磺酸,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化学式I的化合物可以例如,与碱形成盐(例如矿物盐(像碱金属或碱土金属盐,例如钠盐、钾盐或镁盐)),与氨或有机胺(像吗啉、哌啶、吡咯烷、单-、二-或三-低级-烷基胺(例如乙基-、二乙基-、三乙基-或二甲基丙胺),或单-、二-或三羟基-低级-烷基胺(例如单-、二-或三乙醇胺))形成盐。
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或多不饱和的。
卤素一般是氟、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。
烷氧基羰基是例如甲氧基羰基(其为C1烷氧基羰基)、乙氧基羰基、丙氧基羰基、异丙氧基羰基、正丁氧基羰基、叔丁氧基羰基、正戊氧基羰基或己氧基羰基。
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。
在本发明的上下文中,部分饱和或完全饱和的五元至六元芳香族环系统的实例是吡唑、吡咯、吡咯烷、吡咯烷-2-酮、咪唑、三唑和吡啶-2-酮。
在本发明的上下文中,取代基定义中的“单到多取代的”典型地是指,取决于取代基的化学结构,单取代的到七次取代的,优选是单取代的到五次取代的,更优选是单、二或三取代的。
在本发明的上下文中,作为R3的嘧啶或吡啶可以均经由任何碳原子连接至包含取代基G3的环。
根据本发明的具有化学式I的化合物还包括在盐形成期间可以形成的水合物。
优选地,R1是C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C3-C6环烷基-C1-C4烷基、被选自下组的取代基单或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;或R1是被选自下组的取代基单或多取代的C3-C6环烷基-C1-C4烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;
或R1是C2-C6烯基、C2-C6卤代烯基或C2-C6炔基;
R3是氢、卤素、氰基、硝基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C3-C6环烷基-C1-C4烷基,或是被选自下组的取代基单或双取代的C3-C6环烷基,该组由以下各项组成:卤素和氰基;或R3是C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基;或
R3是可以被选自下组的取代基单或多取代的苯基,该组由以下各项组成:卤素、氰基、硝基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、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、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、和-C(O)C1-C4卤代烷基;
或R3是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、C1-C4卤代烷氧基、-C(O)C1-C4卤代烷基、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、或C1-C4烷基磺酰基;或
R3是可以被选自下组的取代基单或多取代的嘧啶,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;或
R3是可以被选自下组的取代基单或多取代的吡啶,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;或
R3是部分饱和或完全饱和的五元至六元芳香族环系统,该环系统经由氮原子连接至包含取代基G3的环,所述环系统可以被选自下组的取代基单或多取代,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基和-C(O)C1-C4烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和–C(O)C1-C4卤代烷基;并且所述环系统包含选自下组的1个、2个或3个杂原子,该组由以下各项组成:氮、氧和硫,其中所述环系统可以不包含多于一个氧原子和不多于一个硫原子。
更优选地,R3是氢、卤素、氰基、硝基、C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C3-C6环烷基-C1-C4烷基,或是被选自下组的取代基单或双取代的C3-C6环烷基,该组由以下各项组成:卤素和氰基;或R3是C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基;或
R3是可以被选自下组的取代基取代的苯基,该组由以下各项组成:卤素、氰基、硝基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、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、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、和-C(O)C1-C4卤代烷基;
或R3是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、C1-C4卤代烷氧基、-C(O)C1-C4卤代烷基、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、或C1-C4烷基磺酰基;或
R3是嘧啶或被选自下组的取代基取代的嘧啶,该组由以下各项组成:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基。
具有化学式I的化合物的优选的组由具有化学式I-1的化合物表示
其中G1、G2、R1和R2a是如上文在化学式I下定义的,X是S、SO或SO2;优选S或SO2;R3是氢、卤素或C1-C4卤代烷基,特别是C1-C4卤代烷基;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。
优选的是具有化学式I-1的化合物,其中G1是C-H;G2是C-H;并且R1、R2a和R3是如上文在化学式I-1下定义的。
还优选的是具有化学式I-1的化合物,其中G1是C-H;G2是C-H;R1是C1-C4烷基、C3-C6环烷基-C1-C4烷基或C3-C6环烷基;R2a是卤素、C1-C4卤代烷基、氰基或可以被选自下组的取代基单或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;并且R3是氢、卤素或C1-C4卤代烷基,优选C1-C4卤代烷基。
还优选的是具有化学式I-1的化合物,其中G1是C-H;G2是C-H;R1是甲基、乙基、正丙基、异丙基或环丙基甲基;R2a是卤素、三氟甲基、氰基或可以被氰基单取代的环丙基;并且R3是氢或三氟甲基。
在具有化学式I-1的进一步优选的化合物中,G1是C-H;G2是C-H;R1是乙基,R2a是三氟甲基,并且R3是氢或三氟甲基。
具有化学式I-1的其他优选化合物是那些,其中G1是C-H;G2是N;并且R1、R2a和R3是如上文在化学式I-1下定义的。
还优选的是具有化学式I-1的化合物,其中G1是C-H;G2是N;R1是C1-C4烷基、C3-C6环烷基-C1-C4烷基或C3-C6环烷基;R2a是卤素、C1-C4卤代烷基、氰基或可以被选自下组的取代基单或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;并且R3是氢、卤素或C1-C4卤代烷基。
具有化学式I-1的进一步优选的化合物是那些,其中G1是C-H;G2是N;R1是甲基、乙基、正丙基、异丙基或环丙基甲基;R2a是卤素、三氟甲基、氰基,或是可以被氰基单取代的环丙基;并且R3是氢或三氟甲基。
进一步优选的是具有化学式I-1的化合物,其中G1是C-H;G2是N;R1是乙基;R2a是三氟甲基;并且R3是氢或三氟甲基。
在具有化学式I-1的其他优选化合物中,G1是CR4;其中R4是如上文在化学式I下定义的;G2是C-H;并且R1、R2a和R3是如上文在化学式I-1下定义的。
还优选的是具有化学式I-1的化合物,其中G1是CR4;其中R4是如上文在化学式I下定义的;G2是C-H;R1是C1-C4烷基、C3-C6环烷基-C1-C4烷基或C3-C6环烷基;R2a是卤素、C1-C4卤代烷基、氰基或可以被选自下组的取代基单或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;并且R3是氢、卤素或C1-C4卤代烷基。
在具有化学式I-1的化合物的进一步优选的组中,G1是CR4;其中R4是如上文在化学式I下定义的;G2是C-H;R1是甲基、乙基、正丙基、异丙基或环丙基甲基;R2a是卤素、三氟甲基、氰基,或是可以被氰基单取代的环丙基;并且R3是氢或三氟甲基。
进一步优选的是具有化学式I-1的化合物,其中G1是CR4;其中R4是如上文在化学式I下定义的;G2是C-H;R1是乙基;R2a是三氟甲基,并且R3是氢或三氟甲基。
进一步优选的是具有化学式I-1的化合物,其中G1是CR4,其中R4是如上文在化学式I下定义的;G2是N;并且R1、R2a和R3是如上文在化学式I-1下定义的。
还优选的是具有化学式I-1的化合物,其中G1是CR4;其中R4是如上文在化学式I下定义的;G2是N;R1是C1-C4烷基、C3-C6环烷基-C1-C4烷基或C3-C6环烷基;R2a是卤素、C1-C4卤代烷基、氰基或是可以被选自下组的取代基单或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;并且R3是氢、卤素或C1-C4卤代烷基。
在具有化学式I-1的化合物的另一个优选的组中,G1是CR4;其中R4是如上文在化学式I下定义的;G2是N;R1是甲基、乙基、正丙基、异丙基或环丙基甲基,R2a是卤素、三氟甲基、氰基或是可以被氰基单取代的环丙基;并且R3是氢或三氟甲基。
进一步优选的是具有化学式I-1的化合物,其中G1是CR4;其中R4是如上文在化学式I下定义的;G2是N;R1是乙基;R2a是三氟甲基;并且R3是氢或三氟甲基。
还优选的是具有化学式I-1的化合物,其中G1是CR4;其中R4是氢、甲基、氰基、氯或溴;G2是C-H;R1是C1-C4烷基、C3-C6环烷基-C1-C4烷基或C3-C6环烷基;R2a是卤素、C1-C4卤代烷基、氰基,或是可以被选自卤素、氰基和C1-C4烷基的取代基单或多取代的C3-C6环烷基;并且R3是氢、卤素或C1-C4卤代烷基。
在具有化学式I-1的另外优选的化合物中,G1是CR4;其中R4是氢、甲基、氰基、氯或溴;G2是C-H;R1是甲基、乙基、正丙基、异丙基或环丙基甲基;R2a是卤素、三氟甲基、氰基,或是可以被氰基单取代的环丙基;并且R3是氢或三氟甲基。
具有化学式I-1的进一步优选的化合物是那些,其中G1是CR4;其中R4是氢、甲基、氰基、氯或溴;G2是C-H;R1是乙基,R2a是三氟甲基,并且R3是氢或三氟甲基。
还优选的是具有化学式I-1的化合物,其中G1是CR4;其中R4是氢、甲基、氰基、氯或溴;G2是N;R1是C1-C4烷基、C3-C6环烷基-C1-C4烷基或C3-C6环烷基;R2a是卤素、C1-C4卤代烷基、氰基或可以被选自下组的取代基单或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;并且R3是氢、卤素或C1-C4卤代烷基。
在具有化学式I-1的化合物的另一个优选的组中,G1是CR4;其中R4是氢、甲基、氰基、氯或溴;G2是N;R1是甲基、乙基、正丙基、异丙基或环丙基甲基;R2a是卤素、三氟甲基、氰基或可以被氰基单取代的环丙基;并且R3是氢或三氟甲基。
在具有化学式I-1的化合物的另一个优选的组中,G1是CR4;其中R4是氢、甲基、氰基、氯或溴,G2是N;R1是乙基,R2a是三氟甲基,并且R3是氢或三氟甲基。
具有化学式I的化合物的另一个优选的组由具有化学式I-2的化合物表示
其中G1、G2、R1和R2a是如上文在化学式I下定义的,X是S、SO或SO2;优选S或SO2;R3是氢、卤素或C1-C4卤代烷基,特别是C1-C4卤代烷基;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。
优选的是具有化学式I-2的化合物,其中G1是C-H;G2是C-H;并且R1、R2a和R3是如上文在化学式I-2下定义的。
还优选的是具有化学式I-2的化合物,其中G1是C-H;G2是C-H;R1是C1-C4烷基、C3-C6环烷基-C1-C4烷基或C3-C6环烷基;R2a是卤素、C1-C4卤代烷基、氰基或可以被选自下组的取代基单或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;并且R3是氢、卤素或C1-C4卤代烷基,优选C1-C4卤代烷基。
还优选的是具有化学式I-2的化合物,其中G1是C-H;G2是C-H;R1是甲基、乙基、正丙基、异丙基或环丙基甲基;R2a是卤素、三氟甲基、氰基或可以被氰基单取代的环丙基;并且R3是氢或三氟甲基。
在具有化学式I-2的进一步优选的化合物中,G1是C-H;G2是C-H;R1是乙基,R2a是三氟甲基,并且R3是氢或三氟甲基。
具有化学式I-2的其他优选化合物是那些,其中G1是C-H;G2是N;并且R1、R2a和R3是如上文在化学式I-2下定义的。
还优选的是具有化学式I-2的化合物,其中G1是C-H;G2是N;R1是C1-C4烷基、C3-C6环烷基-C1-C4烷基或C3-C6环烷基;R2a是卤素、C1-C4卤代烷基、氰基或可以被选自下组的取代基单或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;并且R3是氢、卤素或C1-C4卤代烷基。
具有化学式I-2的进一步优选的化合物是那些,其中G1是C-H;G2是N;R1是甲基、乙基、正丙基、异丙基或环丙基甲基;R2a是卤素、三氟甲基、氰基,或是可以被氰基单取代的环丙基;并且R3是氢或三氟甲基。
进一步优选的是具有化学式I-2的化合物,其中G1是C-H;G2是N;R1是乙基;R2a是三氟甲基;并且R3是氢或三氟甲基。
在具有化学式I-2的其他优选化合物中,G1是CR4;其中R4是如上文在化学式I下定义的;G2是C-H;并且R1、R2a和R3是如上文在化学式I-2下定义的。
还优选的是具有化学式I-2的化合物,其中G1是CR4;其中R4是如上文在化学式I下定义的;G2是C-H;R1是C1-C4烷基、C3-C6环烷基-C1-C4烷基或C3-C6环烷基;R2a是卤素、C1-C4卤代烷基、氰基或可以被选自下组的取代基单或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;并且R3是氢、卤素或C1-C4卤代烷基。
在具有化学式I-2的化合物的进一步优选的组中,G1是CR4;其中R4是如上文在化学式I下定义的;G2是C-H;R1是甲基、乙基、正丙基、异丙基或环丙基甲基;R2a是卤素、三氟甲基、氰基,或是可以被氰基单取代的环丙基;并且R3是氢或三氟甲基。
进一步优选的是具有化学式I-2的化合物,其中G1是CR4;其中R4是如上文在化学式I下定义的;G2是C-H;R1是乙基;R2a是三氟甲基,并且R3是氢或三氟甲基。
进一步优选的是具有化学式I-2的化合物,其中G1是CR4,其中R4是如上文在化学式I下定义的;G2是N;并且R1、R2a和R3是如上文在化学式I-2下定义的。
还优选的是具有化学式I-2的化合物,其中G1是CR4;其中R4是如上文在化学式I下定义的;G2是N;R1是C1-C4烷基、C3-C6环烷基-C1-C4烷基或C3-C6环烷基;R2a是卤素、C1-C4卤代烷基、氰基或是可以被选自下组的取代基单或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;并且R3是氢、卤素或C1-C4卤代烷基。
在具有化学式I-2的化合物的另一个优选的组中,G1是CR4;其中R4是如上文在化学式I下定义的;G2是N;R1是甲基、乙基、正丙基、异丙基或环丙基甲基,R2a是卤素、三氟甲基、氰基或是可以被氰基单取代的环丙基;并且R3是氢或三氟甲基。
进一步优选的是具有化学式I-2的化合物,其中G1是CR4;其中R4是如上文在化学式I下定义的;G2是N;R1是乙基;R2a是三氟甲基;并且R3是氢或三氟甲基。
还优选的是具有化学式I-2的化合物,其中G1是CR4;其中R4是氢、甲基、氰基、氯或溴;G2是C-H;R1是C1-C4烷基、C3-C6环烷基-C1-C4烷基或C3-C6环烷基;R2a是卤素、C1-C4卤代烷基、氰基,或是可以被选自卤素、氰基和C1-C4烷基的取代基单或多取代的C3-C6环烷基;并且R3是氢、卤素或C1-C4卤代烷基。
在具有化学式I-2的另外优选的化合物中,G1是CR4;其中R4是氢、甲基、氰基、氯或溴;G2是C-H;R1是甲基、乙基、正丙基、异丙基或环丙基甲基;R2a是卤素、三氟甲基、氰基,或是可以被氰基单取代的环丙基;并且R3是氢或三氟甲基。
具有化学式I-2的进一步优选的化合物是那些,其中G1是CR4;其中R4是氢、甲基、氰基、氯或溴;G2是C-H;R1是乙基,R2a是三氟甲基,并且R3是氢或三氟甲基。
还优选的是具有化学式I-2的化合物,其中G1是CR4;其中R4是氢、甲基、氰基、氯或溴;G2是N;R1是C1-C4烷基、C3-C6环烷基-C1-C4烷基或C3-C6环烷基;R2a是卤素、C1-C4卤代烷基、氰基或可以被选自下组的取代基单或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基和C1-C4烷基;并且R3是氢、卤素或C1-C4卤代烷基。
在具有化学式I-2的化合物的另一个优选的组中,G1是CR4;其中R4是氢、甲基、氰基、氯或溴;G2是N;R1是甲基、乙基、正丙基、异丙基或环丙基甲基;R2a是卤素、三氟甲基、氰基或可以被氰基单取代的环丙基;并且R3是氢或三氟甲基。
在具有化学式I-2的化合物的另一个优选的组中,G1是CR4;其中R4是氢、甲基、氰基、氯或溴;G2是N;R1是乙基;R2a是三氟甲基,并且R3是氢或三氟甲基。
具有化学式I的化合物的进一步优选的组由具有化学式I-3a的化合物表示
其中
X是S、SO或SO2;优选S或SO2;
R2a是C1-C4卤代烷基或卤素;特别是溴或CF3;
R3是氢、C1-C4卤代烷基、C3-C6环烷基,或是可以被卤素或C1-C4卤代烷基单取代的苯基;
G1是CR4,其中R4是氢、C1-C4烷基、氰基或卤素;特别地R4是氢;
G2是CH或N;特别是CH;并且
A是CH或N;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。
具有化学式I的化合物的进一步优选的组由具有化学式I-3的化合物表示
其中
X是S、SO或SO2;优选S或SO2;
R3是氢、C1-C4卤代烷基、C3-C6环烷基或可以被卤素或C1-C4卤代烷基单取代的苯基;
G1是CR4,其中R4是氢、C1-C4烷基、氰基或卤素;
G2是CH;并且
A是CH或N;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。
具有化学式I的化合物的进一步优选的组由具有化学式I-3的化合物表示其中
X是S、SO或SO2;优选S或SO2;
R3是氢、CF3或可以被卤素单取代的苯基;
G1是CR4,其中R4是氢、C1-C4烷基、氰基或卤素;
G2是N;并且
A是CH或N;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。
在具有化学式I的尤其优选的化合物中,
R1是C1-C4烷基;
R2a是C1-C4卤代烷基或卤素,优选是C1-C4卤代烷基;
R2b是氢;
R3是氢;
G1是CR4;
R4是氢;
G2是CR5;
R5是氢;
G3是CR8;
R8是氢;
X是S或SO2;并且
A是CH或N。
用于制备具有化学式(I)的化合物的根据本发明的方法原则上是通过本领域技术人员已知的方法来进行,或类比文献中(例如在WO 2013/191113中)描述的方法使用适当的起始材料来进行。
更具体地,具有化学式I的化合物(其中X是SO(亚砜)和/或SO2(砜))的亚组可以借助具有化学式I的化合物对应的硫化物(其中X是S)的氧化反应来获得,该氧化反应涉及试剂例如像间氯过氧苯甲酸(mCPBA)、过氧化氢、过硫酸氢钾、高碘酸钠、次氯酸钠或次氯酸叔丁酯以及其他氧化剂。该氧化反应通常是在溶剂的存在下进行的。待用于该反应的溶剂的实例包括脂族卤代烃,如二氯甲烷和氯仿;醇类,如甲醇和乙醇;乙酸;水;及其混合物。待用于该反应的氧化剂的量通常是1至3摩尔,优选地是1至1.2摩尔,相对于1摩尔的化合物I的硫化物,以产生化合物I的亚砜;并且优选地是2至2.2摩尔的氧化剂,相对于1摩尔的化合物I的硫化物,以产生化合物I的砜。此类氧化反应例如披露于WO 2013/018928中。
吲唑、氮杂-吲唑和/或二氮杂-吲唑可以使用熟知的并已描述于例如以下文献中的方法来制备:WO 2013/191113;合成快报(Synlett)(2013),24(12),1573-1577;化学学会化学通讯杂志(Journal of the Chemical Society,Chemical Communications)(1991),(20),1466-7;有机快报(Organic Letters)(2014),16(11),3114-3117;或者关于这种类型的衍生物的更通用合成的综述,参见例如合成科学(Science of Synthesis)(2002),12,227-324和欧洲有机化学杂志(European Journal of Organic Chemistry)(2008),(24),4073-4095。所有这些方法都可以用于获得吲唑衍生物。针对具有化学式I的化合物,一种可能的方法概述于方案1中:
方案1
具有化学式(I)的化合物可以通过在还原环化条件下使用还原剂如亚磷酸三烷酯(更确切地,例如亚磷酸三乙酯)、三烷基膦或三苯基膦,使具有化学式(II)的化合物进行反应来制备。此还原环化的原理类似于已知的卡多根(Cadogan)反应。可替代地,此反应可以在金属催化剂的存在下进行,例如钼(VI)催化剂如MoO2Cl2(dmf)2[氯化氧钼-双(二甲基甲酰胺)],或更通常地用过渡金属络合物与还原剂(如亚磷酸三乙酯、三苯基膦或CO)的组合。适合的溶剂可以包括在室温与200℃之间优选在50℃与160℃之间的温度下,任选地在微波条件下,使用过量的还原剂(如亚磷酸三乙酯),或例如甲苯或二甲苯。
方案2
具有化学式(II)的化合物可以通过通常在加热时并任选地在微波条件下使具有化学式(III)的醛或酮衍生物与具有化学式(IV)的胺衍生物进行反应来制备(方案2)。具有化学式(II)的化合物的形成可需要通过共沸蒸馏或用干燥剂例如像TiCl4或分子筛来去除水。具有化学式(II)的希夫碱的形成对于本领域技术人员而言是非常熟知的,并且方法很好地描述于文献中,参见例如Molbank(2006),M514或马池的高等有机化学:反应、机制和结构(March's Advanced Organic Chemistry:Reactions,Mechanisms,and Structure),第5版,第1185-1187页和其中引用的文献。适合的溶剂可以包括在室温与200℃之间优选50℃与160℃之间的温度下例如甲苯或二甲苯。
具有化学式(III)的化合物是已知的、可商购的或者可以通过本领域的技术人员已知的方法来制备。
具有化学式(IV)的化合物是已知的、可商购的或者可以通过本领域的技术人员已知的方法来制备。
方案3
在方案2中描绘的可替代方法中,具有化学式I的化合物还可以通过使具有化学式V的化合物(其中R2a、R2b、G1、G2具有在化学式I中定义的值)与具有化学式(VI)的化合物(其中Z是离去基团,像例如氟、氯、溴或碘,或芳基-或烷基磺酸盐,或任何其他类似的离去基团)进行反应来制备。例如,这个称为SNAr反应(芳香族亲核取代反应)的反应可以在碱(例如像碳酸钠、碳酸钾或碳酸锂)的存在下,在溶剂(如二甲基甲酰胺)中在室温与200℃之间的温度下,采用或不采用微波辐射来进行。这种类型的反应的实例描述于WO 2007/113596和药物化学杂志(Journal of Medicinal Chemistry),52(22),7170-7185,2009中。在可替代方法中,具有化学式(VI)的化合物(其中Z是氯、溴或碘或任何其他适当的离去基团)可以通过使用铜催化剂偶联条件(例如使用碘化铜(I)作为铜催化剂),用或不用添加剂如L-脯氨酸或N,N’-二甲基乙二胺,在碱(例如像碳酸钾)的存在下,与具有化学式V的化合物偶联。所述可替代方法例如描述于WO 2006/107771和WO 2012/083105中。
具有化学式(V)的化合物是已知的、可商购的或者可以通过本领域的技术人员已知的方法来制备。
具有化学式(VI)的化合物是已知的、可商购的或者可以通过本领域的技术人员已知的方法来制备。一个具体实例描述于方案4中。
方案4
具有化学式(VIa)的化合物(其中R3、R6、R1、A和G3具有在化学式I中定义的值)可以通过具有化学式(XIV)的化合物的氧化来制备(方案4)。该反应可以用像例如过酸(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(像单过氧二硫酸盐或高锰酸钾)的试剂(优先为间氯过苯甲酸)进行。
具有化学式(XIV)的化合物(其中R3、R6、R1、A和G3具有在化学式I中定义的值)可以通过与具有化学式XI的化合物
R1-SH (XI),
或其盐(其中R1是如化学式I中所定义的)的反应而通过具有化学式(VII)的化合物的两个离去基团(LG)的取代来制备(方案4),LG是例如Cl或氟,任选地在适合的碱(如碱金属碳酸盐例如碳酸钠和碳酸钾,或碱金属氢化物如氢化钠,或碱金属氢氧化物如氢氧化钠和氢氧化钾)的存在下,在惰性溶剂中,在优选25℃-120℃之间的温度下进行。待使用的溶剂的实例包括醚,如THF、乙二醇二甲醚、叔丁基甲基醚和1,4-二噁烷;芳香烃,如甲苯和二甲苯;腈,如乙腈;或极性非质子溶剂,如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮或二甲亚砜。具有化学式X的化合物的盐的实例包括具有化学式XIa的化合物
R1-S-M (XIa),
其中R1是如上文定义的并且其中M例如是钠或钾。
在类似条件下,具有化学式(IX)的化合物可以从具有化学式(VIII)的化合物(其中LG是例如Cl或氟,并且LG2是溴或碘)来制备。经由LG2到R3的转化,具有化学式(IX)的化合物到具有化学式(XIV)的化合物的转化可以通过本领域技术人员熟知的方法来进行。例如,具有化学式(XIV)的化合物(其中R6、R1、A和G3具有在化学式I中定义的值,并且R3是例如环丙烷、烯基、炔基、芳基或杂芳基)可以通过具有化学式XIIb的化合物(其中Yb2是三烷基锡衍生物,优选三正丁基锡)与具有化学式XIV的化合物的施蒂勒(Stille)反应来制备。这样的施蒂勒反应通常是在钯催化剂例如四(三苯基膦)钯(0)、或(1,1'双(二苯基膦基)-二茂铁)二氯化钯-二氯甲烷(1:1络合物)的存在下,在惰性溶剂如DMF、乙腈、或二噁烷中,任选地在添加剂如氟化铯或氯化锂的存在下,并且任选地在另外的催化剂例如碘化铜(I)的存在下进行。这样的施蒂勒偶联对于本领域技术人员而言也是熟知的,并且已经描述于例如有机化学杂志(J.Org.Chem.),2005,70,8601-8604,有机化学杂志(J.Org.Chem.),2009,74,5599-5602,以及应用化学国际版本(Angew.Chem.Int.Ed.),2004,43,1132-1136。可替代地,具有化学式(XIV)的化合物(其中R6、R1、A和G3具有在化学式I中定义的值,并且R3是例如环丙烷、烯基、炔基、芳基或杂芳基)可以通过铃木(Suzuki)反应来制备,该反应涉及使具有化学式IX的化合物(其中LG是离去基团,例如氯、溴或碘)与具有化学式XIIa的化合物(其中Yb1可以是硼衍生的官能团,例如像B(OH)2或B(ORb1)2,其中Rb1可以是C1-C4烷基基团或者两个基团ORb1可以与硼原子一起形成五元环,例如像频哪醇硼酸酯)进行反应。该反应可以通过钯基催化剂例如四(三苯基膦)-钯或(1,1'双(二苯基膦基)-二茂铁)二氯化钯-二氯甲烷(1:1络合物),在碱(像碳酸钠或氟化铯)的存在下,在溶剂或溶剂混合物(像例如1,2-二甲氧基乙烷和水的或者二噁烷和水的混合物)中,优选在惰性气氛下来催化。反应温度的范围可以优先是从室温到反应混合物的沸点。这样的铃木反应对于本领域技术人员而言是熟知的,并且已经综述于例如有机金属化学杂志(J.Orgmet.Chem.)576,1999,147–168中。
方案5
具有化学式Ib的化合物(其中A、R1、R2a、R2b、R3、R6、G1、G2和G3具有在化学式I中定义的值)可以通过具有化学式Ia的化合物(其中A、R1、R2a、R2b、R3、R6、G1、G2和G3具有在化学式I中定义的值)的氧化来制备(方案12)。该反应可以用像例如过酸(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(像单过氧二硫酸盐或高锰酸钾)的试剂(优先为间氯过苯甲酸)进行。以类似的方式,具有化学式Ic的化合物(其中A、R1、R2a、R2b、R3、R6、G1、G2和G3具有在化学式I中定义的值)可以通过具有化学式Ib的化合物的氧化来制备。这些反应可以在与这些条件相容的不同有机或水性溶剂中,以从0℃之下直到溶剂系统的沸点的温度进行,并且氧化剂的当量数将决定硫的氧化程度,例如用两个或更多当量的氧化剂,具有化学式Ic的化合物可以直接从具有化学式Ia的化合物制备。
方案6
具有化学式(XV)的化合物可以例如如在方案6中所述的来制备:1)通过使具有化学式(VI)的化合物与一氧化碳在金属催化剂(如钯催化剂,例如:乙酸钯(II))的存在下,在醇(如甲醇或乙醇)中,并且任选地在配体(例如:1,1′-二茂铁二基-双(二苯基膦))的存在下并且任选地在碱(例如:N,N-二乙基乙胺)的存在下进行反应。这些反应在文献中在“芳基卤化物的羰基化交叉偶联(carbonylative cross-coupling of Aryl Halides)”的名称下是熟知的。关于这种反应的实例,参见:应用化学国际版本(Angewandte Chemie,International Edition)(2009),48(23),4114-4133或有机金属化合物(Organometallics)2008,27,5402。2)通过使具有化学式(VII)的化合物进行卤化,该卤化的进行是首先经由在低温下在有机金属(如丁基锂)的存在下具有化学式(VII)的化合物的脱质子化(deprotonative)金属化作用以产生衍生自具有化学式(VII)的化合物的有机金属,随后是与卤素亲电体如碘或溴的反应。这种转化是本领域技术人员熟知的,并且许多试剂可以使用不同的有机金属和用以产生衍生自具有化学式(VII)的化合物的有机金属的条件实现这种转化,关于有关这些类型的反应的一些实例参见:美国化学学会杂志(Journalof the American Chemical Society)1999,121(14),3539-3540或应用化学国际版本(Angewandte Chemie,International Edition)(2014),53(30),7928-7932。3)具有化学式(VIII)的化合物的酯经由标准条件下的还原而还原为醛:例如在还原剂如二异丁基氢化铝的存在下,在试剂如二氯甲烷中,以产生具有化学式(IX)的化合物。这种反应是本领域技术人员熟知的(关于这种转化的实例参见:综合有机转化官能团制备手册(ComprehensiveOrganic Transformations A Guide to Functional Group Preparations),拉罗克(Larock),R.C.1989,第619页(出版商VCH韦因海姆(Weinheim),德国))。4)在溶剂如甲醇中具有化学式(IX)的化合物与具有化学式(X)的化合物的反应产生具有化学式(XI)的化合物和任选地具有化学式(XII)的化合物。5)在溶剂如二甲基甲酰胺中,在或不在微波中,对具有化学式(XI)的化合物加热,产生具有化学式(XIV)的化合物。6)在类似于如方案5中所述的条件中,具有化学式(XIV)的化合物的硫基团的氧化产生所希望的具有化学式(XV)的化合物。
具有化学式(X)的化合物是已知的、可商购的或者可以通过本领域的技术人员已知的方法来制备。
这些反应物可以在碱的存在下发生反应。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(三甲基甲硅烷基)氨基钾、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、苄基三甲基氢氧化铵以及1,8-二氮杂二环[5.4.0]十一-7-烯(DBU)。
这些反应物能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,加入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。
该反应有利地在从约-80℃到约+140℃,优选从约-30℃到约+100℃的温度范围,在许多情况下在介于环境温度与约+80℃之间的范围下进行。
具有化学式I的化合物能以本身已知的方法转化为另一种具有化学式I的化合物,这是通过以常规方式将具有化学式I的该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的一个或多个取代基的替代来实现的。
取决于在每种情况下适合的反应条件和起始材料的选择,有可能的是例如,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。
具有化学式I的化合物的盐能以本身已知的方式进行制备。因此,例如,具有化学式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。
具有化学式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)。
具有化学式I的化合物的盐能以本身已知的方式转化为具有化学式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该反应混合物中沉淀出。
取决于程序或反应条件,具有成盐特性的具有化学式I的化合物能以游离形式或以盐的形式获得。
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化学式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化学式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。
能够以类似方式获得的对映异构体混合物(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,通过用特异性固定酶裂解;通过形成包括化合物,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,例如通过使碱性最终产物外消旋体与光学活性酸(如羧酸,例如樟脑、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,从而给出非对映异构体,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选择性或对映选择性合成的方法,例如通过利用具有合适的立体化学的起始材料进行根据本发明的方法。
可以通过使具有化学式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。此类氧化从文献,例如从药物化学杂志(J.Med.Chem.),32(12),2561-73,1989或WO 00/15615中已知。
如果这些单独的组分具有不同的生物活性,那么有利的是在每种情况下分离或合成在生物学上更有效的异构体,例如对映异构体或非对映异构体,或者异构体混合物,例如对映异构体混合物或非对映异构体混合物。
具有化学式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。
根据以下表1到3的这些化合物可以根据上述的这些方法来制备。随后的这些实例旨在说明本发明并且展示具有化学式I的优选化合物。“Ph”表示苯基基团。
表1:此表披露了具有化学式I-1a的10个化合物:
表1:
化合物编号 | X | R1 | R3 | A |
1.001 | S | -CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH |
1.002 | S(O)<sub>2</sub> | -CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH |
1.003 | S | -CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | N |
1.004 | S(O)<sub>2</sub> | -CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | N |
1.005 | S | -CH<sub>2</sub>CH<sub>3</sub> | H | CH |
1.006 | S(O)<sub>2</sub> | -CH<sub>2</sub>CH<sub>3</sub> | H | CH |
1.007 | S | -CH<sub>2</sub>CH<sub>3</sub> | H | N |
1.008 | S(O)<sub>2</sub> | -CH<sub>2</sub>CH<sub>3</sub> | H | N |
1.009 | S | -CH<sub>2</sub>CH<sub>3</sub> | 4-Cl-Ph- | N |
1.010 | S(O)<sub>2</sub> | -CH<sub>2</sub>CH<sub>3</sub> | 4-Cl-Ph- | N |
以及表1的化合物的N-氧化物。
表2:此表披露了具有化学式I-1b的10个化合物:
表2:
化合物编号 | X | R<sub>1</sub> | R<sub>3</sub> | A |
2.001 | S | -CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH |
2.002 | S(O)<sub>2</sub> | -CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH |
2.003 | S | -CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | N |
2.004 | S(O)<sub>2</sub> | -CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | N |
2.005 | S | -CH<sub>2</sub>CH<sub>3</sub> | H | CH |
2.006 | S(O)<sub>2</sub> | -CH<sub>2</sub>CH<sub>3</sub> | H | CH |
2.007 | S | -CH<sub>2</sub>CH<sub>3</sub> | H | N |
2.008 | S(O)<sub>2</sub> | -CH<sub>2</sub>CH<sub>3</sub> | H | N |
2.009 | S | -CH<sub>2</sub>CH<sub>3</sub> | 4-Cl-Ph- | N |
2.010 | S(O)<sub>2</sub> | -CH<sub>2</sub>CH<sub>3</sub> | 4-Cl-Ph- | N |
以及表2的化合物的N-氧化物。
表3:此表披露了具有化学式I-1c的12个化合物:
表3:
以及表3的化合物的N-氧化物。
根据本发明的具有化学式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、长颚虱属、人虱属、天疱疮属以及木虱属;
来自鞘翅目,例如
缺隆叩甲属、欧洲鳃角金龟(Amphimallon majale)、东方异丽金龟、花象属、蜉金龟属、玉米拟花萤(Astylus atromaculatus)、Ataenius属、甜菜隐食甲(Atomarialinearis)、甜菜胫跳甲、萤叶甲属(Cerotoma spp)、单叶叩甲属、根颈象属、绿金龟、象虫属、圆头犀金龟属、圆头犀金龟属、根萤叶甲属、阿根廷兜虫(Diloboderus abderus)、食植瓢虫属、Eremnus属、黑异爪蔗金龟、咖啡果小蠹、Lagria vilosa、马铃薯甲虫、稻水象属、Liogenys属、Maecolaspis属、栗色绒金龟、Megascelis属、Melighetes aeneus、金龟属、Myochrous armatus、锯谷盗属、耳喙象属(Otiorhynchus spp.)、鳃角金龟属、斑象属、丽金龟属、油菜跳甲属、Rhyssomatus aubtilis、劫根蠹属、金龟子科、米象属、麦蛾属、伪切根虫属、Sphenophorus属、大豆茎象、拟步行虫属、拟谷盗属以及斑皮蠹属;
来自双翅目,例如
伊蚊属、疟蚊属、高梁芒蝇、橄榄果实蝇(Bactrocea oleae)、花园毛蚊、迟眼蕈蚊属(Bradysia spp.)、红头丽蝇、小条实蝇属、金蝇属、库蚊属、黄蝇属、寡鬃实蝇属、地种蝇属、黑腹果蝇、厕蝇属、胃蝇属、Geomyza tripunctata、舌蝇属、皮蝇属、虱蝇属、斑潜蝇属、绿蝇属、潜蝇属、家蝇属、狂蝇属、瘿蚊属、瑞典麦秆蝇、藜泉蝇、草种蝇属、绕实蝇属、Rivelia quadrifasciata、Scatella属、蕈蚊属、刺蝇属、虻属、绦虫属及大蚊属;
来自半翅目,例如
瘤缘蝽(Acanthocoris scabrator)、绿蝽属、苜蓿盲蝽、Amblypelta nitida、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(Horcias nobilellus)、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属、Agalliana ensigera、塔尔吉奥尼木虱(Agonoscenatargionii)、粉虱属(Aleurodicus spp.)、刺粉虱属(Aleurocanthus spp)、甘蔗穴粉虱、软毛粉虱(Aleurothrixus floccosus)、甘蓝粉虱(Aleyrodes brassicae)、棉叶蝉(Amarascabiguttula)、檬果长突叶蝉(Amritodus atkinson)、肾圆盾蚧属、蚜科、蚜属、蚧属(Aspidiotus spp.)、茄沟无网蚜、马铃薯木虱(Bactericera cockerelli)、小粉虱属、短尾蚜属(Brachycaudus spp)、甘蓝蚜、喀木虱属、双尾蚜(Cavariella aegopodii Scop.)、蜡蚧属、褐圆蚧、网籽草叶圆蚧、大叶蝉属(Cicadella spp)、大白叶蝉(Cofana spectra)、隐瘤蚜属、叶蝉属(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、大尾蚜属(Hyalopterus spp)、超瘤蚜种、檬果绿叶蝉(Idioscopus clypealis)、非洲叶蝉(Jacobiasca lybica)、灰飞虱属、球坚蚧、蛎盾蚧属、萝卜蚜(Lopaphis erysimi)、Lyogenys maidis、长管蚜属、沫蝉属(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、狗牙根草芥壳虫(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、三角苜蓿跳虫(Spissistilus festinus)、条斑飞虱(Tarophagus Proserpina)、声蚜属、粉虱属、Tridiscus sporoboli、葵粉蚧属(Trionymus spp.)、非洲木虱、桔矢尖蚧、火焰斑叶蝉(Zygina flammigera)、Zyginidia scutellaris;
来自膜翅目,例如
顶切叶蚁属、三节叶蜂属(Arge spp.)、布切叶白蚁属、茎叶蜂属、松叶蜂属、锯角叶蜂科、松叶蜂(Gilpinia polytoma)、梨实蜂属、毛蚁属、小黄家蚁、新松叶蜂属、农蚁属、Slenopsis invicta、水蚁属以及胡蜂属;
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属、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属、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属、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、Pectinophoragossypiela、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(Richiaalbicosta)、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;
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、栉头蚤属和印鼠客蚤;
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.)、橙花苷硬蓟马(Scirtothrips aurantii)、豆蓟马(Sericothripsvariabilis)、带蓟马属、蓟马属;
来自缨尾目,例如,衣鱼(Lepisma saccharina)。
根据本发明的这些活性成分可以用于控制(即限制或破坏)出现在特别是在植物上,尤其是在农业、园艺和森林中的有用植物和观赏植物上,或在这样的植物的器官如果实、花、叶、秆、块茎或根上的上述类型的有害生物,并且在一些情况下,甚至在较晚的时间点形成的植物器官上仍然针对这些有害生物的保护。
适宜的目标作物具体是,谷物,如小麦、大麦、黑麦、燕麦、水稻、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、茶、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,本发明可以用在任何以下蔬菜物种上: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。
根据本发明的这些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.)。
本发明的这些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虫蛋白;或来自于苏云金芽孢杆菌的杀虫蛋白,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。
在本发明的背景下,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区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,天然产生的毒素的一个或多个氨基酸被置换。在这种氨基酸置换中,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的普通技术人员而言通常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-0 367 474、EP-A-0 401 979以及WO 90/13651中已知。
包含在转基因植物中的毒素使得植物对有害昆虫有耐受性。这些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。此类植物的实例为:(玉米品种,表达Cry1Ab毒素);YieldGard(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毒素以及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),CB Advantage(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,来自先正达种子公司(Syngenta Seeds SAS),霍比特路(Chemin del’Hobit)27,F-31 790圣苏维尔(St.Sauveur),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,来自先正达种子公司,霍比特路27,F-31 790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玉米还转基因地表达PAT酶以达到对除草剂草丁膦铵的耐受性。
3.MIR604玉米,来自先正达种子公司,霍比特路27,F-31 790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,来自孟山都欧洲公司(Monsanto Europe S.A.)270-272特弗伦大道(Avenue de Tervuren),B-1150布鲁塞尔(Brussels),比利时,登记号C/DE/02/9。MON863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。遗传修饰的玉米,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蛋白以获得对除草剂草丁膦铵的耐受性。
7.NK603×MON 810玉米,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/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CP4EPSPS,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-0 392 225)。此类抗病原物质以及能够合成此类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。生产此类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。
作物还包括那些具有对线虫(如大豆异皮线虫)的增加的抗性的作物。
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具有对干旱、高盐、高温、寒冷、霜或光辐射的增加的耐受性的作物。
可以通过这样的转基因植物表达的抗病原物质包括例如离子通道阻断剂,如钠通道和钙通道阻断剂,例如病毒的KP1、KP4或KP6毒素;茋合酶、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);通过微生物产生的抗病原物质,例如植物病原体防御中涉及的肽抗生素类或杂环抗生素类(参见例如WO 95/33818)或蛋白质或多肽因子(所谓的“植物病害抗性基因”,如WO 03/000906中所述的)。
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(如蚊和其他的疾病媒介物;同样参见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,预期了将此类组合物施用于基质,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)。
在一个实施例中,用于控制此类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,预期了施用此类组合物以用于在基质上的有害生物的滞留的控制,该基质是如处于网织品、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 2005/113886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。
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 pearls)、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 armyworm)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(Antoninagraminis))、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、鸟虱和蚤的。
此类寄生虫的实例是:
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、锥蝽属、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物理形式,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、可乳化浓缩剂、微可乳化浓缩剂、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、可乳化颗粒剂、可溶性液体、水可溶性浓缩剂(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标准的发展和使用手册(Manual on Development and Useof FAO and WHO Specifications for Pesticides),联合国,第一版,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、分散体或乳液形式的组合物。这些活性成分还可以与其他佐剂(如精细分散固体、矿物油、植物或动物来源的油、改性的植物或动物来源的油、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包含活性成分。这使活性成分能以受控的量值(例如,缓慢释放)释放到环境中。微胶囊通常具有从0.1微米至500微米的直径。它们含有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酯、或本领域的普通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的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、二甘醇乙醚、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在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;磺基丁二酸盐的二烷基酯,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;以及还有例如在麦卡琴清洁剂和乳化剂年鉴(McCutcheon’s Detergents and Emulsifiers Annual),MC出版公司(MC PublishingCorp.),里奇伍德(Ridgewood),新泽西州(1981)中所述的其他物质。
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、粘度改性剂、悬浮剂、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、棕榈酸和油酸的甲基酯(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除草剂佐剂纲要(Compendium of HerbicideAdjuvants),第10版,南伊利诺伊大学,2010。
本发明组合物通常包括按重量计从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。
施用量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组成(重量%):
可乳化浓缩剂:
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%
以下实例进一步展示了(但不限制)本发明。
<u>可湿性粉剂</u> | 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,从而获得了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。
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,从而获得了可以直接用于种子处理的粉剂。
<u>可乳化浓缩剂</u> | |
活性成分 | 10% |
辛基苯酚聚乙二醇醚(4-5mol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的乳液可以通过用水稀释从这种浓缩物中获得。
<u>尘剂</u> | 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该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法敷料。
<u>挤出机颗粒剂</u> | |
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,并且将该混合物用水湿润。将混合物挤出并且然后在空气流中干燥。
<u>包衣的颗粒剂</u> | |
活 | 8% |
聚乙二醇(分子量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到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。
将这种精细研磨的组合与这些佐剂紧密地混合,从而给出了悬浮液浓缩物,可以使用水稀释从该浓缩物获得任何所希望稀释度的悬浮液。使用此类稀释体,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雾、倾倒或浸渍进行保护。
<u>种子处理用的可流动性浓缩剂</u> | |
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%的乳液的形式) | 0.2% |
水 | 45.3% |
将这种精细研磨的组合与这些佐剂紧密地混合,从而给出了悬浮液浓缩物,可以使用水稀释从该浓缩物获得任何所希望稀释度的悬浮液。使用此类稀释体,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雾、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。向此乳液中添加在5.3份的水中的2.8份的1,6-己二胺混合物。将该混合物搅拌直至聚合反应完成。将获得的胶囊悬浮剂通过添加0.25份的增稠剂以及3份的分散剂进行稳定。该胶囊悬浮剂配制品包含28%的活性成分。该介质胶囊的直径是8微米-15微米。将所得配制品施用到种子上作为适用于此目的的装置中的水性悬浮液。
配制品类型包括乳液浓缩剂(EC)、悬浮液浓缩剂(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或300MHz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。
LCMS方法:
方法A(HPLC纯化):
柱:Gemini-NX C18(75x 30mm–5mm,110A)
流动相:A(水)-B(乙腈)
流速:50ml/min
分析条件:
方法B-标准:(SQD-ZDQ-ZCQ)
在来自沃特斯(Waters)的质谱仪(SDQ、SQDII或ZQ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:正离子或负离子,毛细管:3.00kV,锥孔范围:30V-60V,萃取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:0L/Hr,去溶剂化气体流量:650L/Hr;质量范围:100Da至900Da)以及来自沃特斯的Acquity UPLC:二元泵、加热管柱室以及二极管阵列检测器)。溶剂脱气装置,二元泵,加热管柱室以及二极管阵列检测器。柱:沃特斯UPLC HSS T3,1.8mm,30x 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C-标准长:(SQD-ZDQ-ZCQ)
在来自沃特斯的质谱仪(SDQ、SQDII或ZQ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:正离子或负离子,毛细管:3.00kV,锥孔范围:30V-60V,萃取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:0L/Hr,去溶剂化气体流量:650L/Hr;质量范围:100Da至900Da)以及来自沃特斯的Acquity UPLC:二元泵、加热管柱室以及二极管阵列检测器)。溶剂脱气装置,二元泵,加热管柱室以及二极管阵列检测器。柱:沃特斯UPLC HSS T3,1.8mm,30x 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D-非极性:(SQD-ZDQ-ZCQ)
在来自沃特斯的质谱仪(SDQ、SQDII或ZQ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:正离子或负离子,毛细管:3.00kV,锥孔范围:30V-60V,萃取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:0L/Hr,去溶剂化气体流量:650L/Hr;质量范围:100Da至900Da)以及来自沃特斯的Acquity UPLC:二元泵、加热管柱室以及二极管阵列检测器)。溶剂脱气装置,二元泵,加热管柱室以及二极管阵列检测器。柱:沃特斯UPLC HSS T3,1.8mm,30x 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:40%-100%B,在1.2min内;流量(ml/min)0.85
方法E-GCMS方法:标准CI/EI
在赛默(Thermo)MS:DSQ和GC:TRACE GC ULTRA上用来自塞夫龙菲罗门(Zebronphenomenex)的柱进行GCMS:相ZB-5ms 15m,直径:0.25mm,0.25μm,H2流1.7ml/min,注射器温度:250℃,检测器温度:220℃,方法:在70℃开始,25℃/min直至320℃,在320℃保持2min,总时间12min。
CI试剂气体:甲烷,流量1ml/min
实例P1:2-(2-乙基硫烷基苯基)-6-(三氟甲基)吡唑并[4,3-c]吡啶(化合物
1.005)
步骤A:5-甲基-2-(三氟甲基)吡啶1-氧化物
将5-甲基-2-三氟甲基-吡啶(可商购,0.164g)溶解于二氯甲烷(5mL)中。添加间氯过氧苯甲酸(m-CPBA,0.486g),并且将混合物在环境温度(rt)下搅拌48小时。将溶剂在减压下去除并且将粗产物通过层析法纯化(溶剂:异己烷/乙醚7/3到乙醚)以给出呈白色固体的标题化合物(120mg)。1H NMR(300MHz,CDCl3):δ(ppm)8.17(s,1H),7.57(d,1H),7.16(d,1H),2.38(s,3H)ppm。
步骤B:5-甲基-4-硝基-2-(三氟甲基)吡啶1-氧化物
将5-甲基-2-(三氟甲基)吡啶1-氧化物(步骤A,0.787g)于硫酸H2SO4(3ml)中的溶液用硝酸HNO3(4ml)和硫酸(2mL)的溶液在0℃下进行处理。将反应在100℃下搅拌两小时。然后,将反应混合物用冰淬灭,并且将pH通过添加水性氢氧化钠NaOH(4.0M)而调节到7。将所得溶液用二氯甲烷萃取三次。将合并的有机层用盐水洗涤,并用硫酸钠进行干燥并进行浓缩。将混合物通过用己烷和乙醚洗脱来快速层析而纯化,以给出5-甲基-4-硝基-2-(三氟甲基)吡啶1-氧化物(0.45g)。1H NMR(300MHz,CDCl3):δ(ppm)8.42(s,1H),8.22(s,1H),2.68(s,3H)ppm。
步骤C:5-甲基-4-硝基-2-(三氟甲基)吡啶
将5-甲基-4-硝基-2-(三氟甲基)吡啶1-氧化物(步骤B,0.475g)用三氯化磷(1.13g)进行处理。将混合物在100℃下加热20分钟。将残余物通过层析法(异己烷/乙醚7/3)进行纯化以给出5-甲基-4-硝基-2-(三氟甲基)吡啶(0.38g)。1H NMR(300MHz,CDCl3):δ(ppm)8.85(s,1H),8.16(s,1H),2.70(s,3H)ppm。
步骤D:4-硝基-6-(三氟甲基)吡啶-3-甲醛
将5-甲基-4-硝基-2-(三氟甲基)吡啶(步骤C,0.399g)和N,N-二甲基-甲酰胺二甲基乙缩醛(0.361g)于二甲基甲酰胺(2ml)中的混合物在120℃下搅拌2小时。将溶剂在真空下蒸发,并且将残余物倾倒入偏高碘酸钠NaIO4(1.192g)溶解于四氢呋喃(THF)和水(25ml:25ml)中的混合物中。将混合物搅拌16小时。将反应混合物进行过滤,并且将水层用乙酸乙酯萃取三次。将合并的有机层进行浓缩。将混合物通过快速层析法(己烷和乙醚)进行纯化,以给出4-硝基-6-(三氟-甲基)吡啶-3-甲醛(0.405g)。1H NMR(300MHz,CDCl3):δ(ppm)10.56(s,1H),9.32(s,1H),8.32(s,1H)。
步骤E:N-(2-乙基硫烷基苯基)-1-[4-硝基-6-(三氟甲基)-3-吡啶基]甲亚胺
将4-硝基-6-(三氟甲基)吡啶-3-甲醛(步骤D,0.22g)和2-(乙硫基)苯胺(可商购,0.142g)于甲苯中的混合物在70℃在微波下搅拌40分钟。将反应混合物通过快速层析法(异己烷和乙醚)进行纯化以给出N-(2-乙基硫烷基苯基)-1-[4-硝基-6-(三氟甲基)-3-吡啶基]甲亚胺(0.319g)。1H NMR(300MHz,CDCl3):δ(ppm)9.82(s,1H),8.97(s,1H),8.25(s,1H),7.23(m,3H),7.11(m,1H),2.99(q,2H),1.39(t,3H)ppm。
步骤F:2-(2-乙基硫烷基苯基)-6-(三氟甲基)吡唑并[4,3-c]吡啶(化合物1.005)
将N-(2-乙基硫烷基苯基)-1-[4-硝基-6-(三氟甲基)-3-吡啶基]甲亚胺(步骤E,0.19g)和三苯基膦(0.54g)于甲苯(10mL)中的混合物在回流下搅拌30分钟。将溶剂在真空中进行蒸发,并且将残余物通过快速层析法(异己烷和乙醚)进行纯化,以给出2-(2-乙基硫烷基苯基)-6-(三氟甲基)吡唑并[4,3-c]吡啶(标题化合物1.005,0.165g)。1H NMR(300MHz,CDCl3):δ(ppm)9.36(s,1H),8.56(s,1H),8.10(s,1H),7.54(m,3H),7.40(m,1H),2.82(q,2H),1.21(t,3H)ppm。
实例P2:2-(2-乙基磺酰基苯基)-6-(三氟甲基)吡唑并[4,3-c]吡啶(化合物
1.006)
向2-(2-乙基硫烷基苯基)-6-(三氟甲基)吡唑并[4,3-c]吡啶(0.085g)于二氯甲烷(5mL)中的溶液添加间氯过氧苯甲酸m-CPBA(0.107g)。将所得黄色溶液在室温下搅拌过夜。将反应终止,并且将溶剂进行蒸发。将残余物通过快速层析法(乙醚)进行纯化以给出2-(2-乙基磺酰基苯基)-6-(三氟甲基)吡唑并[4,3-c]吡啶(标题化合物1.006,0.076g)。1HNMR(400MHz,CDCl3):9.38(s,1H),8.61(s,1H),8.26(d,1H),8.04(s,1H),7.85(m,2H),7.59(d,1H),3.23(q,2H),1.24(t,3H)ppm。
实例P3:2-(3-乙基硫烷基-2-吡啶基)-6-(bl)吡唑并[4,3-c]吡啶(化合物1.007)
向6-(三氟甲基)-2H-吡唑并[4,3-c]吡啶(0.5g)和3-乙基硫烷基-2-氟-吡啶(0.4g,如在EP 341011中所述的来制备)于二甲基甲酰胺(5mL)中的溶液中添加碳酸二锂(0.2g,3mmol)。将所得溶液在100℃下搅拌过夜。将反应通过添加水来终止,并且将水层用乙酸乙酯萃取三次。将合并的有机层用硫酸镁干燥并在真空下浓缩。将残余物通过快速层析法(环己烷/乙酸乙酯)进行纯化,以给出2-(3-乙基硫烷基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]吡啶(化合物1.007,0.053g)。1H NMR(400MHz,CDCl3):9.37(d,1H),8.98(d,1H),8.37(dd,1H),8.14(s,1H),7.86(dd,1H),7.43(dd,1H),2.96(q,2H),1.32(t,3H)ppm。反应的主要产物是位置异构体。
将化合物P5(6-溴-2-(3-乙基硫烷基-2-吡啶基)吡唑并[4,3-c]吡啶)使用相同的反应用6-(溴)-2H-吡唑并[4,3-c]吡啶作为起始材料进行制备。1H NMR(400MHz,CDCl3):9.09(s,1H),8.89(s,1H),8.36(d,1H),7.93(s,1H),7.84(dd,1H),7.42(dd,1H),2.94(q,2H),1.34(t,3H)ppm。
实例P4:2-(3-乙基磺酰基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]吡啶(化合物
1.008)
向2-(3-乙基硫烷基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]吡啶(化合物1.007)(0.044g)于二氯甲烷(2.7mL)中的溶液中添加间氯过氧苯甲酸(m-CPBA)(0.080g)。将所得黄色溶液在环境温度下搅拌2小时。将反应通过添加水来终止,并且将水层用二氯甲烷萃取三次。将合并的有机层用NaOH 1M的溶液进行洗涤,用硫酸镁进行干燥,并且在真空下进行浓缩。将残余物通过快速层析法(环己烷/乙酸乙酯)进行纯化,以给出2-(3-乙基磺酰基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]吡啶(化合物1.008,0.048g)。1H NMR(400MHz,CDCl3):9.39(s,1H),8.92(s,1H),8.84(d,1H),8.65(dd,1H),8.04(s,1H),7.76(dd,1H),3.94(q,2H),1.44(t,3H)ppm。
将化合物P6(6-溴-2-(3-乙基磺酰基-2-吡啶基)吡唑并[4,3-c]吡啶)使用相同的反应用6-溴-2-(3-乙基硫烷基-2-吡啶基)吡唑并[4,3-c]吡啶作为起始材料进行制备。1HNMR(400MHz,CDCl3):9.10(s,1H),8.82(m,2H),8.64(dd,1H),7.83(s,1H),7.72(dd,1H),3.91(q,2H),1.41(t,3H)ppm。
实例P7:2-[3-乙基磺酰基-5-(三氟甲基)-2-吡啶基]-6-(三氟甲基)吡唑并[4,3-
c]吡啶
步骤A:2-溴-3-乙基硫烷基-5-(三氟甲基)吡啶
向乙基硫烷基钠(2.70g,1.1当量)于30ml THF中的悬浮液中添加四丁基溴化铵(0.35g,0.05当量)。在20min内逐滴添加2-溴-3-氟-5-(三氟甲基)吡啶(5g)于20ml四氢呋喃中的溶液。温度在这个时间内从20℃上升到35℃。将混合物用硅藻土进行过滤,并且在真空下进行浓缩。将残余物通过快速层析法(环己烷/乙酸乙酯)纯化两次,以给出2-溴-3-乙基硫烷基-5-(三氟甲基)吡啶(1.5g)。1H NMR(400MHz,CDCl3):8.38(s,1H),7.52(s,1H),3.02(q,2H),1.44(m,3H)ppm。
步骤B:2-[3-乙基硫烷基-5-(三氟甲基)-2-吡啶基]-6-(三氟甲基)吡唑并[4,3-c]吡啶
将2-溴-3-乙基硫烷基-5-(三氟甲基)吡啶(0.2g,0.699mmol)、6-(三氟甲基)-2H-吡唑并[4,3-c]吡啶(0.399g,2.13mmol)、磷酸钾(0.445g,2.097mmol)、碘化铜(iodocopper)(0.033g,0.175mmol)和反式-n,n'-二甲基-1,2-环己烷二胺(0.0497g,0.055mL,0.35mmol)于甲苯(9.1mL)中的混合物进行搅拌,并且在120℃下加热过夜。在冷却后,将150mg的2-溴-3-乙基硫烷基-5-(三氟甲基)吡啶和相同量的CuI、反式-n,n'-二甲基-1,2-环己烷二胺和磷酸钾添加至混合物中。将反应在120℃下再搅拌一晚。将反应通过添加水和乙酸乙酯的溶液来终止。将水层用乙酸乙酯萃取三次。将合并的有机层用盐水然后用水洗涤,用硫酸镁进行干燥并在真空下浓缩。将残余物通过快速层析法(环己烷/乙酸乙酯)进行纯化以给出2-[3-乙基硫烷基-5-(三氟甲基)-2-吡啶基]-6-(三氟甲基)吡唑并[4,3-c]吡啶(0.091g)和其位置异构体。1H NMR(400MHz,CDCl3):9.39(s,1H),9.13(s,1H),8.58(s,1H),8.15(s,1H),8.00(s,1H),3.03(q,2H),1.41(t,3H)ppm。
步骤C:2-[3-乙基磺酰基-5-(三氟甲基)-2-吡啶基]-6-(三氟甲基)吡唑并[4,3-c]吡啶
使用实例P4中所述的相似条件,将标题化合物通过2-[3-乙基硫烷基-5-(三氟甲基)-2-吡啶基]-6-(三氟甲基)吡唑并[4,3-c]吡啶(如先前所述制备)与m-CPBA在二氯甲烷中进行反应来制备。1H NMR(400MHz,CDCl3)δppm1.51(t,3H),4.10(q,2H),8.05(s,1H),8.89(d,1H),9.04(d,1H),9.09(s,1H),9.42(s,1H)。
实例P8:2-(5-溴-3-乙基磺酰基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]吡啶
步骤A:5-溴-2,3-双(乙基硫烷基)吡啶
向5-溴-2,3-二氟-吡啶(可商购,13.61g,66.65mmol)和N,N-二甲基甲酰胺(94.4g,100mL)的溶液中分三份添加乙硫醇钠(18.44g,173.3mmol):该反应是放热的。将所得溶液在室温下搅拌两小时。将反应通过添加水和乙酸乙酯的溶液来终止。将水层用乙酸乙酯萃取三次。将合并的有机层用盐水然后用水洗涤,用硫酸镁进行干燥并在真空下浓缩。将残余物不进行额外纯化而用在下一步骤中。1H NMR(400MHz,CDCl3):8.32(s,1H),7.56(s,1H),3.18(q,2H),2.95(q,2H),1.40-1.32(m,6H)ppm。
步骤B:5-溴-2,3-双(乙基磺酰基)吡啶
向用冰浴冷却的5-溴-2,3-双(乙基硫烷基)吡啶(13.6g,48.9mmol)于二氯甲烷(250mL)中的溶液中添加间氯过氧苯甲酸(45.6g,198mmol)。将所得溶液在室温下搅拌一小时。将反应通过添加硫代硫酸钠的溶液来终止,并且将水层用二氯甲烷萃取三次。将合并的有机层用NaOH 1M的溶液进行洗涤,用硫酸镁进行干燥,并且在真空下进行浓缩。将残余物通过快速层析法(环己烷/乙酸乙酯)进行纯化,以给出5-溴-2,3-双(乙基磺酰基)吡啶(6.54g)。1H NMR(400MHz,CDCl3):9.00(s,1H),8.76(s,1H),3.78(q,2H),3.64(q,2H),1.44-1.34(m,6H)ppm。
步骤C:2-(5-溴-3-乙基磺酰基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]吡啶(P8)
向6-(三氟甲基)-2H-吡唑并[4,3-c]吡啶(0.4679g,2.425mmol)和5-溴-2,3-双(乙基磺酰基)吡啶(0.83g,2.425mmol)于二甲基甲酰胺(19mL)中的溶液中添加碳酸二锂(0.5523g,7.276mmol)。将所得溶液在130℃下搅拌两小时,然后在110℃下搅拌过夜。将反应通过添加水和乙酸乙酯来终止。将水层用乙酸乙酯萃取三次。将合并的有机层用硫酸镁干燥并在真空下浓缩。将残余物通过HPLC(参见方法A)进行纯化,以给出2-(5-溴-3-乙基磺酰基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]吡啶(化合物P8,0.017g)。1HNMR(400MHz,CDCl3)δppm 1.47(t,3H),3.99(q,2H)8.03(s,1H)8.76(d,1H)8.88(d,1H)8.91(d,1H)9.40(s,1H)。反应的其他产物是位置异构体(1-(5-溴-3-乙基磺酰基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]吡啶),并且反应的主要产物是溴化物的取代物(1-[5,6-双(乙基磺酰基)-3-吡啶基]-6-(三氟甲基)吡唑并[4,3-c]吡啶)。
实例P9:2-(5-环丙基-3-乙基磺酰基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]吡
啶:
步骤A:5-环丙基-2,3-双(乙基硫烷基)吡啶:
将用氩气冲洗的20mL密封小瓶装填上5-溴-2,3-双(乙基硫烷基)吡啶(1.00g,3.59mmol),然后装填环丙基硼酸(1.16g,12.9mmol)、四(三苯基膦)钯(0)(0.416g,0.359mmol)、磷酸三钾(4.72g,1.84mL,21.6mmol)、甲苯(4.33g,5mL,46.8mmol)和水(5.000g,5mL,277.5mmol)。然后,将混合物回流2小时。将反应通过添加水和乙酸乙酯的溶液来终止。将水层用乙酸乙酯萃取三次。将合并的有机层用硫酸镁干燥并在真空下浓缩。将残余物通过快速层析法(环己烷/乙酸乙酯)进行纯化,以给出标题化合物(0.625mg)。1HNMR(400MHz,CDCl3):8.12(s,1H),7.18(s,1H),3.18(q,2H),2.92(q,2H),1.82(m,1H),1.39(t,3H),1.30(t,3H),0.98(m,2H),0.68(m,2H)ppm。
步骤B:5-环丙基-2,3-双(乙基磺酰基)吡啶:
使用实例P8(步骤B)中描述的相似条件,将标题化合物通过5-环丙基-2,3-双(乙基硫烷基)吡啶(如先前所述制备)与m-CPBA在二氯甲烷中进行反应来制备。1H NMR(400MHz,CDCl3)δppm 0.94(m,2H),1.22-1.45(m,8H)2.10(m,1H),3.62(q,2H),3.75(q,2H),8.12(s,1H),8.67(s,1H)。
步骤C:2-(5-环丙基-3-乙基磺酰基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]吡啶:
使用实例P8(步骤C)中描述的相似条件,将化合物P9通过6-(三氟甲基)-2H-吡唑并[4,3-c]吡啶和5-环丙基-2,3-双(乙基磺酰基)吡啶(如先前所述制备)的反应来制备。1HNMR(400MHz,CDCl3)δppm 0.95(m,2H),1.28(m,2H),1.40(t,3H),2.13(m,1H),3.85(q,2H),8.03(s,1H),8.17(d,1H),8.57(d,1H),8.84(d,1H),9.37(s,1H)。
实例P10:2-(3-乙基磺酰基-5-苯基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]吡
啶:
步骤A:2,3-双(乙基硫烷基)-5-苯基-吡啶:
将用氩气冲洗的20mL密封小瓶装填上5-溴-2,3-双(乙基硫烷基)吡啶(1.00g,3.59mmol),然后装填苯基硼酸(1.63g,12.9mmol)、四(三苯基膦)钯(0)(0.208g,0.180mmol)、磷酸三钾(4.72g,1.84mL,21.6mmol)、甲苯(4.33g,5mL,46.8mmol)和水(5.000g,5mL,277.5mmol)。然后,将混合物回流2小时。将反应通过添加水和乙酸乙酯的溶液来终止。将水层用乙酸乙酯萃取三次。将合并的有机层用硫酸镁干燥并在真空下浓缩。将残余物通过快速层析法(环己烷/乙酸乙酯)进行纯化,以给出标题化合物(0.97g)。LC-MS(方法B)RT 1.29(276,MH+)。
使用描述的相似条件,制备5-(4-氯苯基)-2,3-双(乙基硫烷基)吡啶。LC-MS(方法B)RT 1.36(311,MH+)
使用描述的相似条件,制备2,3-双(乙基硫烷基)-5-[3-(三氟甲基)苯基]吡啶。LC-MS(方法B)RT 1.36(344,MH+)。
步骤B:2,3-双(乙基磺酰基)-5-苯基-吡啶:
使用实例P8(步骤B)中描述的相似条件,将标题化合物(2,3-双(乙基磺酰基)-5-苯基-吡啶)通过2,3-双(乙基硫烷基)-5-苯基-吡啶(如先前所述制备)与m-CPBA在二氯甲烷中进行反应来制备。LC-MS(方法B)RT 0.92(340,MH+)
使用实例P8(步骤B)中描述的相似条件,将5-(4-氯苯基)-2,3-双(乙基磺酰基)吡啶通过5-(4-氯苯基)-2,3-双(乙基硫烷基)吡啶(如先前所述制备)与m-CPBA在二氯甲烷中进行反应来制备。LC-MS(方法B)RT 0.99(374,MH+)
使用实例P8(步骤B)中描述的相似条件,将2,3-双(乙基磺酰基)-5-[3-(三氟甲基)苯基]吡啶通过2,3-双(乙基硫烷基)-5-[3-(三氟甲基)苯基]吡啶(如先前所述制备)与m-CPBA在二氯甲烷中进行反应来制备。LC-MS(方法B)RT 1.02(408,MH+)。
步骤C:2-(3-乙基磺酰基-5-苯基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]吡啶:
使用实例P8(步骤C)中描述的相似条件,将标题化合物P10通过6-(三氟甲基)-2H-吡唑并[4,3-c]吡啶和2,3-双(乙基磺酰基)-5-苯基-吡啶(如先前所述制备)的反应来制备。1H NMR(400MHz,CDCl3)δppm 1.47(t,3H),3.96(q,2H),7.54-7.63(m,3H),7.68-7.76(m,2H),8.06(s,1H),8.80(d,1H),8.95(s,1H),9.02(d,1H),9.41(s,1H)。
使用实例P8(步骤C)中描述的相似条件,将化合物P11通过6-(三氟甲基)-2H-吡唑并[4,3-c]吡啶和5-(4-氯苯基)-2,3-双(乙基磺酰基)吡啶(如先前所述制备)的反应来制备。1H NMR(400MHz,CDCl3)δppm 1.47(t,3H),3.98(q,2H),7.54-7.60(m,2H),7.62-7.69(m,2H),8.06(s,1H),8.77(d,1H)8.96(s,1H),8.99(d,1H)9.41(s,1H)。
使用实例P8(步骤C)中描述的相似条件,将化合物P12通过6-(三氟甲基)-2H-吡唑并[4,3-c]吡啶和2,3-双(乙基磺酰基)-5-[3-(三氟甲基)苯基]吡啶(如先前所述制备)的反应来制备。1H NMR(400MHz,CDCl3)δppm 1.49(t,3H),4.02(q,2H),7.69-7.78(m,1H),7.79-7.86(m,1H),7.91(d,1H),7.94(s,1H),8.06(s,1H),8.81(d,1H),8.98(d,1H),9.04(d,1H),9.41(s,1H)。
实例P11:2-(3-乙基磺酰基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]哒嗪PP1: 实例PP1
步骤A:乙基-6-(三氟甲基)哒嗪-3-甲酸酯:
将3-氯-6-(三氟甲基)哒嗪(4.5g,22mmol,如在四面体(Tetrahedron),65(21),4212-4219,2009中所述来制备的)、1,1′-二茂铁二基-双(二苯基膦)(0.74g,1.3mmol)、乙酸钯(II)(0.10g,0.44mmol)、N,N-二乙基乙胺(2.7g,3.7mL,27mmol)于乙醇(100mL)中的溶液用CO(25巴)在氢化器皿中进行加压,并且在120℃搅拌5h。LCMS分析显示这时之后反应完成。然后将反应混合物进行冷却,并且进行过滤并且将滤液在真空中进行浓缩。将粗产物通过Comb快速层析法用120g的柱以及环己烷+0-70%乙酸乙酯的梯度进行纯化,以给出呈米色固体的标题化合物。
LCMS(标准方法A);保留时间0.73min,221(MH+)。
1H NMR(400MHz,氯仿-d)δppm:1.51(t,J=7.15Hz,3H);4.60(q,J=6.97Hz,2H);8.00(d,J=8.80Hz,1H);8.39(d,J=8.80Hz,1H)。
步骤B:乙基-4-碘代-6-(三氟甲基)哒嗪-3-甲酸酯:
(2,2,6,6-四甲基-1-哌啶基)锂(TMPLi)溶液(0.63M于THF中)是通过在-40℃将nBuLi(2.17ml,5.00mmol,2.3M于己烷中)缓慢添加至(2,2,6,6-四甲基-1-哌啶基)于THF(5ml)中的溶液中伴随搅拌30min来制备的。
通过在具有隔片的烧瓶中在真空下在140℃干燥氯化锂(1.2g)持续5h来制备氯化锂溶液(0.7M于THF中)。在冷却之后,添加干THF(40ml),并且继续搅拌直到所有的盐溶解。
在氩气下在干燥的双颈烧瓶(10ml)中,将乙基-6-(三氟甲基)哒嗪-3-甲酸酯(0.150g,0.681mmol)溶解于四氢呋喃(3mL,0.681mmol)中,并且用在THF中的氯化锂溶液(2mL,1.50mmol,如上所述制备)处理,并且用氯化锌(II)(1mL,0.749mmol)进行处理。将所得混合物冷却至-78℃,并且然后在-78℃逐滴(10min)添加TMPLi(1.6mL,1.02mmol,如上所述制备)。将反应混合物在-78℃搅拌1小时,并且然后逐滴添加溶解于1ml的THF中的分子碘(0.173g,0.681mmol),并且将所得混合物在-78℃再搅拌20min。这时之后的LC-MS和GC-MS仅显示希望的产物。允许反应混合物加温至室温,并且用饱和水性氯化铵淬灭,将有机相依次用硫代硫酸钠和盐水进行洗涤,用Na2SO4进行干燥,进行过滤,并且在真空中进行浓缩。将粗品通过Combi快速层析法用12g的柱和环己烷+0-40%乙酸乙酯的梯度进行纯化,以给出标题化合物。
GCMS(化学电离,方法E):保留时间,4.60min,347(MH+)
1H NMR(400MHz,氯仿-d)δppm 1.49(t,J=7.15Hz,3H)4.58(q,J=6.97Hz,2H)8.40(s,1H)。
步骤C:4-碘代-6-(三氟甲基)哒嗪-3-甲醛:
将4-碘代-6-(三氟甲基)哒嗪-3-甲酸乙酯(0.3g,0.86695mmol)于二氯甲烷(4.5mL)中的溶液在-78℃冷却下来,并且通过在-70℃至-78℃下逐滴添加的二异丁基氢化铝(DIBAL,1.7339mL,1.7339mmol)进行处理。将反应混合物在-78℃搅拌1h,并且然后允许加温至室温,并且搅拌一晚上。然后将反应混合物冷却至0℃,并且小心地用饱和NH4Cl进行淬灭,并且然后将pH用10%HCl调为酸性。将混合物用EtOAc(3X)进行萃取,将合并的有机层用盐水进行洗涤,用Na2SO4进行干燥,进行过滤,并且在真空中进行浓缩。将粗产物通过Combi快速层析法用12g的柱和环己烷+0-60%乙酸乙酯的梯度进行纯化,以给出纯的标题产物。
LCMS(标准方法A);保留时间0.81min,303(MH+)。
1H NMR(400MHz,氯仿-d)δppm:8.52(s,1H);10.32(s,1H)。
步骤D:(3-乙基硫烷基-2-吡啶基)肼:
向3-乙基硫烷基-2-氟-吡啶(可商购或如在WO 8910694中所述制备的,9.70g,61.7mmol)于1,4-二噁烷(100mL)中的溶液中添加一水合肼(12.0g,11.7mL,370mmol)。将所得溶液回流过夜。将反应通过添加水和乙酸乙酯来终止。将水层用乙酸乙酯萃取三次。将合并的有机层用硫酸镁进行干燥,并且在真空下进行浓缩以给出呈纯化合物的(3-乙基硫烷基-2-吡啶基)肼(9.23g,88.4%产率)。1H NMR(400MHz,CDCl3)δppm:8.12(d,1H),7.55(d,1H),6.72(sb,1H),6.62(m,1H),3.98(sb,2H),2.75(q,2H),1.22(t,3H)。
步骤E:3-乙基硫烷基-N-[(E)-[4-[2-(3-乙基硫烷基-2-吡啶基)肼基]-6-(三氟甲基)哒嗪-3-基]亚甲基氨基]吡啶-2-胺:
在氩气下,在烧瓶中,在室温下将4-碘代-6-(三氟甲基)哒嗪-3-甲醛(0.077g,0.25498mmol)和(3-乙基硫烷基-2-吡啶基)肼(在步骤D中制备,0.053g,0.28mmol)在甲醇(3.03g,3.83mL,94.3mmol)中搅拌48h。LCMS和TLC分析显示起始材料的消耗是完全的。将反应混合物在真空中进行浓缩,并且将粗产物通过Combi快速层析法用12g的柱和环己烷+0-100%乙酸乙酯的梯度进行纯化。这给出处于1:1的比例的标题化合物和3-乙基硫烷基-N-[(Z)-[4-碘代-6-(三氟甲基)哒嗪-3-基]亚甲基氨基]吡啶-2-胺的混合物。将此混合物不经进一步纯化而用于下一步骤。
LCMS(标准方法A);保留时间1.06min,494(MH+)(标题化合物)。混合物中的第二种化合物是3-乙基硫烷基-N-[(Z)-[4-碘代-6-(三氟甲基)哒嗪-3-基]亚甲基氨基]吡啶-2-胺:LCMS(标准方法A);保留时间0.99min,454(MH+)。
步骤F:2-(3-乙基硫烷基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]哒嗪:
在微波小瓶中,将在步骤E中获得的产物溶解于DMF中,并且将所得混合物在160℃在微波条件下搅拌10min。将DMF通过在65℃在真空中蒸发来去除,并且将残余物溶解于叔丁基甲基醚和水中,将有机层分离并且然后依次用硫代硫酸钠饱和水溶液、水和盐水进行洗涤,用Na2SO4干燥,进行过滤,并且在真空中进行浓缩。将粗产物通过Combi快速层析法用4g的柱、用环己烷+0-50%乙酸乙酯的梯度来纯化。
第一洗脱产物是副产物:1-(3-乙基硫烷基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]哒嗪。LCMS(标准方法A);保留时间0.95min,326(MH+)。
第二洗脱产物:2:2-(3-乙基硫烷基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]哒嗪。
LCMS(标准方法A);保留时间0.93min,326(MH+)。
1H NMR(400MHz,氯仿-d)δppm:1.36(t,J=7.34Hz,3H);2.99(q,J=7.46Hz,2H);7.50(dd,J=8.07,4.77Hz,1H);7.91(dd,J=8.07,1.47Hz,1H);8.32(s,1H);8.43(dd,J=4.77,1.47Hz,1H);9.60(d,J=1.10Hz,1H)。
步骤G:2-(3-乙基磺酰基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]哒嗪(PP1):
将1-(3-乙基硫烷基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]哒嗪(15mg,0.046mmol)溶解于二氯甲烷(2mL)中,并且在0℃缓慢添加3-氯过苯甲酸(21.7mg,0.097mmol)。将所得混合物在0℃搅拌30min,并且然后在室温搅拌过夜。在此时之后,添加另外1当量的m-CPBA,并且将反应混合物在室温搅拌30min,到这时候LCMS显示反应完成。将反应混合物用2ml的NaOH 1N和2ml的硫代硫酸钠饱和水溶液淬灭。将混合物搅拌10min,并且然后将水层用10ml的二氯甲烷萃取3次。将合并的有机层用10ml的NaOH 1N进行洗涤,用Na2SO4进行干燥,进行过滤并且在真空中进行浓缩,以给出呈黄色油状物的标题化合物。
LCMS(标准方法A);保留时间0.82min,358(MH+)。
1H NMR(400MHz,氯仿-d)δppm 1.46(t,J=7.34Hz,3H);3.93(q,J=7.70Hz,2H);7.84(dd,J=8.07,4.77Hz,1H);8.24(s,1H);8.69(dd,J=7.89,1.65Hz,1H);8.92(dd,J=4.77,1.83Hz,1H);9.53(d,J=1.10Hz,1H)。
表4:具有化学式(Ia)的化合物的实例(“Ph”表示苯基基团):
表5:具有化学式(Ia)的化合物的实例
通过添加其他有杀昆虫、杀螨和/或杀真菌活性的成分,根据本发明的组合物的活性可以显著地加宽,并且适合于当时的环境。具有化学式I的化合物与其他具有杀昆虫、杀螨和/或杀真菌活性的成分的混合物还可以具有另外的意料之外的优点,这些优点还可以在更宽的含义上描述为协同活性。例如,植物对其更好的耐受性、降低的植物毒性,昆虫可以在它们的不同发育阶段得到控制或者在它们的生产期间(例如,在研磨或者混合过程中,在它们的储藏或它们的使用过程中)更好的行为。
在这里,合适的活性成分的添加物是例如下面类别的活性成分的代表物:有机磷化合物、硝基苯酚衍生物、硫脲、保幼激素、甲脒、二苯甲酮衍生物、脲类、吡咯衍生物、氨基甲酸酯、拟除虫菊酯、氯化烃、酰基脲、吡啶基亚甲基氨基衍生物、大环内酯类、新烟碱以及苏云金芽孢杆菌制剂。
以下具有化学式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至5中的化合物组成”):
一种佐剂,该佐剂选自由以下物质组成的组:石油(别名)(628)+TX,
一种杀螨剂,该杀螨剂选自由以下物质组成的组: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、氨基硫代盐(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、AZ60541(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、苯茵灵(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、氟氯菊酯(76)+TX、乐杀螨(907)+TX、溴灭菊酯(别名)+TX、溴烯杀(bromocyclene)(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、丁酮威(butylpyridaben)(别名)+TX、石硫合剂(calcium polysulfide)(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(研究代码)(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11(696)+TX、瓜叶菊素(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(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、二硝酯(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、多拉克汀(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(研究代码)(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、庚烯醚(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、苄丙二腈(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、米尔螨素(557)+TX、杀螨茵素肟(milbemycin oxime)(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-152(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(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(研究代码)(1382)+TX、RA-17(研究代码)(1383)+TX、鱼藤酮(722)+TX、八甲磷(schradan)(1389)+TX、硫线磷(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(研究代码)(1404)+TX、舒非仑(别名)[CCN]+TX、氟虫胺(sulfluramid)(750)+TX、治螟磷(sulfotep)(753)+TX、硫黄(754)+TX、S21-121(研究代码)(757)+TX、氟胺氰菊酯(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、久效威(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、苏力菌素(thuringiensin)(别名)[CCN]+TX、威茵磷(triamiphos)(1441)+TX、苯噻螨(triarathene)(1443)+TX、三唑磷(820)+TX、唑呀威(triazuron)(别名)+TX、敌百虫(824)+TX、氯苯乙丙磷(trifenofos)(1455)+TX、甲杀螨霉素(trinactin)(别名)(653)+TX、灭蚜硫磷(847)+TX、氟吡唑虫(vaniliprole)[CCN]和YI-5302(化合物代码)+TX,
一种杀藻剂,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、茵多酸(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,
一种驱蠕虫剂,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,
一种杀鸟剂,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,
一种杀细菌剂,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,
一种生物试剂,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(Amblyseius spp.)(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、短距蚜小蜂(Aphelinus abdominalis)(别名)(33)+TX、棉蚜寄生蜂(Aphidius colemani)(别名)(34)+TX、食蚜瘿蚊(Autographacalifornica NPV)(别名)(35)+TX、苜蓿银纹夜蛾核多角体病毒(Bacillus firmus)(别名)(38)+TX、坚硬芽孢杆菌(Bacillus firmus)(别名)(48)+TX、球形芽孢杆菌(Bacillussphaericus Neide)(学名)(49)+TX、苏云金芽孢杆菌(Bacillus thuringiensisBerliner)(学名)(51)+TX、苏云金芽孢杆菌鲇泽亚种(Bacillus thuringiensissubsp.aizawai)(学名)(51)+TX、苏云金芽孢杆菌以色列亚种(Bacillus thuringiensissubsp.israelensis)(学名)(51)+TX、苏云金芽孢杆菌日本亚种(Bacillus thuringiensissubsp.japonensis)(学名)(51)+TX、苏云金芽孢杆菌库尔斯塔克亚种(Bacillusthuringiensis subsp.kurstaki)(学名)(51)+TX、苏云金芽孢杆菌拟步行甲亚种(Bacillus thuringiensis subsp.tenebrionis)(学名)(51)+TX、球孢白僵茵(Beauveriabassiana)(别名)(53)+TX、布氏白僵茵(Beauveria brongniartii)(别名)(54)+TX、草蜻蛉(Chrysoperla carnea)(别名)(151)+TX、孟氏隐唇瓢虫(Cryptolaemus montrouzieri)(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(Dacnusa sibirica)(别名)(212)+TX、豌豆潜叶蝇姬小蜂(Diglyphus isaea)(别名)(254)+TX、丽蚜小蜂(Encarsia formosa)(学名)(293)+TX、桨角蚜小蜂(Eretmoceruseremicus)(别名)(300)+TX、玉米穗夜蛾核多角体病毒(Helicoverpa zea NPV)(别名)(431)+TX、嗜茵异小杆线虫(Heterorhabditis bacteriophora)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(Macrolophus caliginosus)(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、黄绿绿僵茵(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(Paecilomyces fumosoroseus)(别名)(613)+TX、智利捕植螨(Phytoseiuluspersimilis)(别名)(644)+TX、甜菜夜蛾(Spodoptera exigua multicapsid)多核衣壳核多角体病毒(学名)(741)+TX、毛蚊线虫(Steinernema bibionis)(别名)(742)+TX、小卷蛾斯氏线虫(Steinernema carpocapsae)(别名)(742)+TX、夜蛾斯氏线虫(别名)(742)+TX、Steinernema glaseri(别名)(742)+TX、Steinernema riobrave(另名)(742)+TX、Steinernema riobravis(别名)(742)+TX、Steinernema scapterisci(别名)(742)+TX、斯氏线虫属(Steinernema spp.)(别名)(742)+TX、赤眼蜂属(别名)(826)+TX、西方盲走螨(Typhlodromus occidentalis)(别名)(844)和蜡蚧轮枝茵(Verticillium lecanii)(别名)(848)+TX,
一种土壤消毒剂,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,
一种化学不育剂,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,
一种昆虫信息素,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、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、lineatin(别名)[CCN]+TX、litlure(别名)[CCN]+TX、粉纹夜蛾性诱剂(looplure)(别名)[CCN]+TX、诱杀酯(medlure)[CCN]+TX、megatomoic acid(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、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trunc-call(别名)[CCN]+TX,
一种昆虫驱避剂,该昆虫驱避剂选自以下物质组成的组: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、避蚊胺[CCN]+TX、驱蚊酯(dimethyl carbate)[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(别名)[CCN]+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、狄氏刑(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,
一种杀软体动物剂,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,
一种杀线虫剂,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、苯茵灵(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、依马克丁(别名)[CCN]+TX、苯甲酸依马克丁(291)+TX、依立诺克丁(291)+TX、(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、激动素(kinetin)(别名)[CCN]+TX、糠氨基嘌呤(mecarphon)(别名)(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、疣孢漆斑茵(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、thiafenox(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,
一种硝化作用抑制剂,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,
一种植物激活剂,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(Reynoutria sachalinensis)提取物(别名)(720)+TX,
一种杀鼠剂,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,
一种增效剂,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,
一种动物驱避剂,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,
一种杀病毒剂,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,
一种创伤保护剂,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)和甲基硫茵灵(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(硝基thal-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、SYP-LI90(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、IKF-916(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-羧酸(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-羧酸(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(Acremoniumalternatum)+TX+TX、顶头孢霉(Acremonium cephalosporium)+TX+TX、Acremonium diospyri+TX、Acremoniumobclavatum+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NRRL21882+TX、曲霉属+TX、出芽短梗霉+TX、固氮螺菌属+TX、(+TX、TAZO)+TX、固氮菌属+TX、圆褐固氮菌+TX、孢囊固氮菌(BionaturalBlooming)+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(BioNem-)+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QST 2808(+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Cry2Ae+TX、苏云金芽孢杆菌Cry1Ab+TX、苏云金芽孢杆菌鲇泽亚种(Bacillusthuringiensis aizawai)GC 91+TX、苏云金芽孢杆菌以色列亚种(Bacillusthuringiensis israelensis)(+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BMP 123+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(Clavipacter michiganensis)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(Bacillus thuringiensis 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(Cedeceadravisae)+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(Cupriavidus campinensis)+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、汉逊德巴利酵母+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(Halomonas subglaciescola)+TX、盐弧菌变型(Halovibriovariabilis)+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、Penicillium billai(+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(Pseudomonas aureofasciens)(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-A22UL(Sporodex)+TX、纵沟柄锈菌(Puccinia canaliculata)+TX、Puccinia thlaspeos(Wood)+TX、侧雄腐霉菌(Pythium paroecandrum)+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(Tilletiopsis minor)+TX、铁艾酵母属+TX、棘孢木霉(T34)+TX、盖姆斯木霉(Trichoderma gamsii)+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LC 52+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(Ulocladiumoudemansii)(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、Virgibaclillus marismortui+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:松树油+TX、印楝素(Plasma Neem+TX、+TX、+TX、Molt-+TX、植物学IGR+TX、菜籽油(Lilly Miller)+TX、土荆芥near ambrosioides+TX、菊花提取物+TX、印楝油提取物+TX、唇形科精油+TX、丁香迷迭香薄荷油和百里香精油提取物(Garden insect)+TX、甜菜碱+TX、大蒜+TX、柠檬草油+TX、印楝油+TX、猫薄荷(猫薄荷油)+TX、Nepetacatarina+TX、烟碱+TX、牛至油+TX、胡麻科油+TX、除虫菊+TX、皂皮树+TX、大虎杖(+TX、)+TX、鱼藤酮(Eco)+TX、芸香料植物提取物+TX、大豆油(Ortho)+TX、茶树油(Timorex)+TX、百里香精油+TX、MMF+TX、+TX、迷迭香芝麻胡椒薄荷百里香与肉桂提取物的混合物(EF)+TX、丁香迷迭香和胡椒薄荷提取物的混合物(EF)+TX、丁香胡椒薄荷大蒜油与薄荷的混合物(Soil)+TX、高岭土+TX、褐藻存储glucam+TX;以及
信息素,包括:黑头萤火虫信息素(3M喷洒型黑头萤火虫)+TX、苹果蠹蛾信息素(派拉蒙分配器(Paramount dispenser)-(CM)/Isomate C-)+TX、葡萄卷叶蛾信息素(3M MEC-GBM喷洒型 )+TX、卷叶虫信息素(3M MEC–LR喷洒型)+TX、家蝇信息素(Snip7Fly+TX、Starbar Premium Fly)+TX、梨小食心虫信息素(3M梨小食心虫喷洒型)+TX、桃树钻心虫信息素(Isomate-)+TX、番茄蛲虫信息素(3M喷洒型)+TX、Entostat粉(来自棕榈树的提取物)(Exosex)+TX、十四烷三烯基乙酸酯+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、薰衣草千里酸酯;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+TX、粉虱细蜂(Amitus hesperidum)+TX、原缨翅缨小蜂(Anagrus atomus)+TX、暗腹长索跳小蜂(Anagyrus fusciventris)+TX、卡玛长索跳小蜂(Anagyrus kamali)+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(Aphidiuscolemani)+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、Cirrospilus ingenuus+TX、Cirrospilus quadristriatus+TX、白星橘啮小蜂(Citrostichus phyllocnistoides)+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、Diaparsisjucunda+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(Eretmoceruseremicus)+TX、哥德恩蚜小蜂(Encarsia guadeloupae)+TX、海地恩蚜小蜂(Encarsia haitiensis)+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、Fopiusceratitivorus+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(Hypoaspisaculeifer)(Aculeifer-+TX、Entomite-)+TX、兵下盾螨(Hypoaspis miles)(Hypoline+TX、Entomite-)+TX、黑色枝跗瘿蜂+TX、Lecanoideus floccissimus+TX、Lemophagus errabundus+TX、三色丽突跳小蜂(Leptomastidea abnormis)+TX、Leptomastix dactylopii+TX、长角跳小蜂(Leptomastix epona)+TX、Lindorus lophanthae+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(Orius insidiosus)(+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、Pseudacteontricuspis+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)(complex)+TX、胯姬小蜂属+TX、Rhyzobius lophanthae+TX、澳洲瓢虫+TX、Ruminadecollate+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、Thripobius semiluteus+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(LillyMiller Worry 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(SemasporeOrganic Grasshopper)+TX、粘着陷阱(Trapline+TX、Rebell)+TX以及陷阱(Takitrapline y+)+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“杀有害生物剂手册(The PesticideManual)”[杀有害生物剂手册-一本世界手册(The Pesticide Manual-A WorldCompendium);第十三版;编者:C.D.S.汤姆林(TomLin);英国农作物保护委员会(TheBritish Crop Protection Council)]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“阿巴美丁”在条目编号(1)之下进行了描述。当以上对特定化合物加入“[CCN]”时,所讨论的化合物包括在“杀有害生物剂通用名纲要(Compendium of Pesticide Common Names)”中,该纲要在互联网上可得:[A.伍德(Wood);杀有害生物剂通用名纲要(Compendium of Pesticide Common Names),版权1995-2004];例如,化合物“乙酰虫腈”在互联网地址http://www.alanwood.net/pesticides/acetoprole.html下进行了描述。
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。如果名称不是“通用名”,那么对于特定化合物在圆括号内给出了作为代替而使用的该名称的性质;在这种情况下,使用IUPAC名称、IUPAC/化学文摘名称、“化学名称”、“传统名称”、“化合物名称”、或“研究代码”,或者如果既没有使用这些名称之一,也没有使用“通用名”,那么使用的是“别名”。“CAS登记号”意指化学文摘登记号。
选自表1至5的具有化学式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至5的化合物和如上所述的活性成分,优选地处于从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,甚至更尤其是从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至5的具有化学式I的化合物以及一种或多种如上描述的活性成分的混合物可以例如以单一的“掺水即用”的形式施用,以组合的喷雾混合物(该混合物由这些单一活性成分的单独配制品构成)(例如“桶混制剂”)施用,并且当以顺序的方式(即,一个在另一个适度短的时期之后,如几小时或几天)施用时组合使用这些单一活性成分来施用。施用选自表1至5的具有化学式I的化合物和如上所述的活性成分的顺序对于实施本发明而言并不是至关重要的。
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。
组合物的施用方法、也就是说控制以上提及的类型的有害生物的方法,如喷雾、雾化、洒粉、涂刷、敷料、散射或倾倒,选择这些方式以适合当时环境的既定目标;以及这些组合物用于控制以上提及的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,优选地在0.1与500ppm之间的活性成分。每公项的施用量通常是每公项1到2000g活性成分,尤其是10到1000g/ha,优选地10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,活性成分可以通过根系统(内吸作用)到达植物,这是通过用液体组合物将这些植物的场所浸透或者通过将固体形式的活性成分掺入植物的场所(例如掺入土壤,例如以颗粒的形式(土施))来实现的。在水稻作物的情况下,这样的颗粒剂可以被计量加入淹水的稻田中。
本发明的化合物及其组合物还适合于保护植物繁殖材料(例如种子,如果实、块茎或籽粒,或者苗圃植物)对抗上述类型的有害生物。可以用化合物在种植前对繁殖材料进行处理,例如可以在播种前对种子进行处理。可替代地,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固体组合物层来实现的。当繁殖材料被种植在施用处时,还可能的是例如在条播期间将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如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待控制的植物和有害生物/真菌,并且通常在每100kg种子1克至200克之间,优选在每100kg种子5克至150克之间,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优选实施例中是指真正的种子。
本发明还包括用具有化学式I的化合物包衣或处理的种子或含有具有化学式I的化合物的种子。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,活性成分在种子的表面,尽管成分的更多或更少的部分可以渗透到种子材料中,这取决于施用的方法。当所述种子产品被(再)种植时,它可以吸收活性成分。在一个实施例中,本发明使得其上粘附有具有化学式(I)的化合物的植物繁殖材料可得。此外,由此可得包括用具有化学式(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,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化学式(I)的化合物的种子处理施用,如在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:
实例B1:对抗烟粉虱(棉粉虱)的活性:
将棉花叶圆片置于24孔微量滴定板中的琼脂上并且用从10'000ppmDMSO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施用率下得到至少80%的死亡率:P1和P2。
实例B2:对抗黄瓜条叶甲(玉米根虫)的活性
将置于24孔微量滴定板中的琼脂层上的玉米芽通过喷雾用从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,针对死亡率对这些样品进行评估。
以下化合物在200ppm施用率下得到至少80%的死亡率:
P1、P2、P3、P4、P6、P7、P8、P9、PP1、P10、P11和P12。
实例B3:对抗大豆褐椿(Euschistus heros)(新热带褐臭蝽)的活性
将24孔微量滴定板中的琼脂上的大豆叶用从10'000ppm DMSO储备溶液中制备的水性测试溶液进行喷雾。干燥之后,将叶用N-2期若虫进行侵染。侵染5天之后,相比于未处理样品,针对生长抑制对这些样品进行评估。
以下化合物在200ppm施用率下给出了两个类别(死亡率或生长抑制)中至少一个的至少80%的效果:
P1、P3、P4、P7、P8、PP1、P10、P11和P12。
实例B4:对抗桃蚜(碧桃蚜)的活性:
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10'000ppmDMSO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施用率下得到至少80%的死亡率:
P1、P2、P3、P4、P6、P7、P8、PP1、P10和P11。
实例B5:对抗桃蚜(碧桃蚜)的活性:
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测试率下得到至少80%的死亡率:P2和P4。
实例B6:对抗桃蚜(碧桃蚜)的活性:
将来自10'000ppm DMSO储备溶液的测试化合物通过移液管施用到24孔微量滴定板中并且与蔗糖溶液进行混合。将这些平板用拉伸的Parafilm膜进行封闭。将24孔塑料模板置放在平板上并且将经过侵染的豌豆幼苗直接置放在Parafilm膜上。将经过侵染的平板用凝胶印迹纸与另外的塑料模板进行封闭,并且然后倒置。侵染5天之后,针对死亡率对这些样品进行评估。
以下化合物在12ppm测试率下得到至少80%的死亡率:P1和P3。
实例B7:对抗小菜蛾(Plutella xylostella)(小菜蛾(Diamond back moth))的活
性
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施用率下给出了两个类别(死亡率或生长抑制)中至少一个的至少80%的效果:
P1、P2、P3、P4、P7、P8、PP1、P10、P11和P12。
实例B8:对抗海灰翅夜蛾(埃及棉叶虫)的活性:
将棉花叶圆片置于24孔微量滴定板中的琼脂上并且用从10'000ppmDMSO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。测试样品对海灰翅夜蛾的控制为在死亡率、拒食效果、以及生长抑制中的至少一个比未处理样品更高时。
以下化合物在200ppm施用率下得到至少80%的控制:
P1、P2、P3、P4、P7、P8、P9、PP1、P10、P11和P12。
实例B9:对抗海灰翅夜蛾(埃及棉叶虫)的活性:
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,根已经将化合物吸收并且莴苣已经生长进入盖平板。现在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)中的至少一个的至少80%的效果:
P1、P3、P4和P7。
实例B10:对抗二点叶螨(二斑叶螨)的活性:摄食/接触活性:
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,将叶圆片用混合年龄的螨种群进行侵染。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。
以下化合物在200ppm施用率下得到至少80%的死亡率:P10。
实例B11:对抗烟蓟马(葱蓟马)的活性摄食/接触活性:
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10’000ppmDMSO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蓟马种群进行侵染。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施用率下得到至少80%的死亡率:P10。
实例B11:对抗埃及伊蚊(黄热病蚊子)的活性:
将10至15只伊蚊幼虫(L2期)连同营养混合物置于96孔微量滴定板中。将测试化合物用移液管吸取到这些孔中。在孵育2天时间之后,针对死亡率和生长抑制对昆虫进行评估。
以下化合物在5ppm测试比率下给出了两个类别(死亡率或生长抑制)中的至少一个的至少80%的效果:P1和P7。
Claims (8)
1.一种具有化学式I的化合物,
其中
A是CH、N或CR7;其中R7是C1-C4烷基、C1-C4卤代烷基、氰基、硝基或卤素;
X是S、SO或SO2;
R1是C1-C4烷基、C1-C4卤代烷基、C3-C6环烷基、C3-C6环烷基-C1-C4烷基、被选自下组的取代基单或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基、C1-C4卤代烷基和C1-C4烷基;或
R1是被选自下组的取代基单或多取代的C3-C6环烷基-C1-C4烷基,该组由以下各项组成:卤素、氰基、C1-C4卤代烷基和C1-C4烷基;或
R1是C2-C6烯基、C2-C6卤代烯基或C2-C6炔基;
R2a和R2b彼此独立地是氢、卤素、氰基、C1-C6卤代烷基或被一个或两个选自下组的取代基取代的C1-C6卤代烷基,该组由以下各项组成:羟基、甲氧基和氰基;或
R2a和R2b彼此独立地是C1-C4卤代烷基硫基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、C1-C4卤代烷氧基、或–C(O)(C1-C4卤代烷基);或
R2a和R2b彼此独立地是可以被选自下组的取代基单或多取代的C3-C6环烷基,该组由以下各项组成:卤素、氰基、C1-C4卤代烷基和C1-C4烷基;
R3是氢、卤素、氰基、硝基、C1-C6烷基、C1-C6烷氧基、C1-C4烷氧基C1-C4烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6环烷基-C1-C4烷基,或
R3是被选自下组的取代基单或双取代的C3-C6环烷基,该组由以下各项组成:卤素、C1-C4烷基、C1-C4卤代烷基和氰基;或
R3是C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基;或
R3是可以被选自下组的取代基单或多取代的苯基,该组由以下各项组成:卤素、氰基、硝基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷氧基C1-C4烷基、C1-C4卤代烷基硫基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、和-C(O)C1-C4卤代烷基;或
R3是C1-C6卤代烷基硫基、C1-C6卤代烷基亚磺酰基、C1-C6卤代烷基磺酰基、C1-C6卤代烷氧基、-C(O)C1-C4卤代烷基、C1-C6烷基硫基、C1-C6烷基亚磺酰基、或C1-C6烷基磺酰基;或
R3是可以被选自下组的取代基单或多取代的嘧啶基,该组由以下各项组成:卤素、氰基、硝基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷氧基C1-C4烷基、C1-C4卤代烷基硫基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基和-C(O)C1-C4卤代烷基;或
R3是可以被选自下组的取代基单或多取代的吡啶基,该组由以下各项组成:卤素、氰基、硝基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷氧基C1-C4烷基、C1-C4卤代烷基硫基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基硫基、C1-C4烷基亚磺酰基、或C1-C4烷基磺酰基和-C(O)C1-C4卤代烷基;或
R3是部分饱和或完全饱和的五元至六元芳香族环系统,该环系统经由氮原子连接至包含取代基G3的环,所述环系统可以被选自下组的取代基单或多取代,该组由以下各项组成:卤素、氰基、硝基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4烷氧基C1-C4烷基、C1-C4烷基硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、-C(O)C1-C4烷基、C1-C4卤代烷基硫基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;所述环系统包含选自下组的1个、2个或3个杂原子,该组由以下各项组成:氮、氧和硫;其中所述环系统可以不包含多于一个氧原子和不多于一个硫原子;
R6是氢、C1-C4烷基、C1-C4卤代烷基、卤素或氰基;
G1是CR4,其中R4是氢、C1-C4烷基、C1-C4卤代烷基、氰基或卤素;
G2是N或CR5,其中R5是氢、C1-C4烷基、C1-C4卤代烷基、氰基、硝基或卤素;
G3是N或CR8,其中R8是氢、C1-C4烷基、C1-C4卤代烷基、卤素或氰基;以及具有化学式I的化合物的农用化学上可接受的盐、立体异构体、对映异构体和互变异构体。
2.根据权利要求1所述的具有化学式I的化合物,由具有化学式I-1的化合物表示
其中X、G1、G2、R1和R2a是如权利要求1中在化学式I下定义的;R3是氢、卤素或C1-C4卤代烷基。
3.根据权利要求1所述的具有化学式I的化合物,由具有化学式I-2的化合物表示
其中X、G1、G2、R1和R2a是如权利要求1中在化学式I下定义的;R3是氢、卤素或C1-C4卤代烷基。
4.一种具有化学式I的化合物,是由具有化学式I-3a的化合物表示
其中
X是S、SO或SO2;R2a是C1-C4卤代烷基或卤素;R3是氢、C1-C4卤代烷基、C3-C6环烷基,或是可以被卤素或C1-C4卤代烷基单取代的苯基;
G1是CR4,其中R4是氢、C1-C4烷基、氰基或卤素;G2是CH或N;并且
A是CH或N。
5.根据权利要求1所述的具有化学式I的化合物,由具有化学式I-3的化合物表示
其中
X是S、SO或SO2;
R3是氢、C1-C4卤代烷基、C3-C6环烷基或可以被卤素或C1-C4卤代烷基单取代的苯基;
G1是CR4,其中R4是氢、C1-C4烷基、氰基或卤素;
G2是CH或N;并且
A是CH或N。
6.一种杀有害生物组合物,该杀有害生物组合物包含至少一种根据权利要求1所述的具有化学式I的化合物或适当时其互变异构体作为活性成分以及至少一种助剂,该化合物在所有情况下为游离形式或为农用化学上可用的盐形式。
7.一种用于控制有害生物的方法,该方法包括将根据权利要求6所述的组合物施用于这些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。
8.一种用于保护植物繁殖材料免受有害生物攻击的方法,该方法包括用根据权利要求6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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