CN112585137A - 杀有害生物活性的二环杂芳香族化合物 - Google Patents
杀有害生物活性的二环杂芳香族化合物 Download PDFInfo
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- CN112585137A CN112585137A CN201980052540.5A CN201980052540A CN112585137A CN 112585137 A CN112585137 A CN 112585137A CN 201980052540 A CN201980052540 A CN 201980052540A CN 112585137 A CN112585137 A CN 112585137A
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- CCEKAJIANROZEO-UHFFFAOYSA-N sulfluramid Chemical compound CCNS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CCEKAJIANROZEO-UHFFFAOYSA-N 0.000 description 1
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- 150000003456 sulfonamides Chemical class 0.000 description 1
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- JPUVICMZRAJSAW-UHFFFAOYSA-N tert-butyl 4-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-oxoimidazo[4,5-b]pyridine-1-carboxylate Chemical compound ClC=1SC(=CN=1)CN1C=2C(=CC=C1)N(C(N=2)=O)C(=O)OC(C)(C)C JPUVICMZRAJSAW-UHFFFAOYSA-N 0.000 description 1
- RDELVWNIQYPMLN-UHFFFAOYSA-N tert-butyl 4-[(2-chloro-1,3-thiazol-5-yl)methyl]-5-methyl-2-oxoimidazo[4,5-b]pyridine-1-carboxylate Chemical compound ClC=1SC(=CN=1)CN1C=2C(=CC=C1C)N(C(N=2)=O)C(=O)OC(C)(C)C RDELVWNIQYPMLN-UHFFFAOYSA-N 0.000 description 1
- YKUQUJFBGWUUDO-UHFFFAOYSA-N tert-butyl 4-[(6-chloropyridin-3-yl)methyl]-2,2-dioxo-[1,2,5]thiadiazolo[3,4-b]pyridine-1-carboxylate Chemical compound ClC1=CC=C(C=N1)CN1C=2C(=CC=C1)N(S(N=2)(=O)=O)C(=O)OC(C)(C)C YKUQUJFBGWUUDO-UHFFFAOYSA-N 0.000 description 1
- NLJDBTZLVTWXRG-UHFFFAOYSA-N tert-butylazanium;iodide Chemical compound [I-].CC(C)(C)[NH3+] NLJDBTZLVTWXRG-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YJINQJFQLQIYHX-UHFFFAOYSA-N tetradec-11-enyl acetate Chemical compound CCC=CCCCCCCCCCCOC(C)=O YJINQJFQLQIYHX-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 239000004577 thatch Substances 0.000 description 1
- 125000005304 thiadiazolidinyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- MBNMHBAJUNHZRE-UHFFFAOYSA-M thiosultap monosodium Chemical compound [Na+].OS(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O MBNMHBAJUNHZRE-UHFFFAOYSA-M 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- FUSNMLFNXJSCDI-UHFFFAOYSA-N tolnaftate Chemical compound C=1C=C2C=CC=CC2=CC=1OC(=S)N(C)C1=CC=CC(C)=C1 FUSNMLFNXJSCDI-UHFFFAOYSA-N 0.000 description 1
- 229960004880 tolnaftate Drugs 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 231100000440 toxicity profile Toxicity 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- UGCNRZFAUBJVPT-UHFFFAOYSA-N tricyclohexyltin;hydrate Chemical compound O.C1CCCCC1[Sn](C1CCCCC1)C1CCCCC1 UGCNRZFAUBJVPT-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
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- 150000003672 ureas Chemical class 0.000 description 1
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 1
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- 239000004034 viscosity adjusting agent Substances 0.000 description 1
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- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002578 wasp venom Substances 0.000 description 1
- 239000004565 water dispersible tablet Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 239000002676 xenobiotic agent Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
Classifications
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- 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
-
- 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
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/12—Powders or granules
- A01N25/14—Powders or granules wettable
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Toxicology (AREA)
- Dispersion Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
一种具有式(I)的化合物,其中取代基是如在权利要求1中所定义的,以及那些化合物的农用化学上可接受的盐、立体异构体、对映异构体、互变异构体和N‑氧化物,可以用作杀昆虫剂。
Description
本发明涉及杀有害生物活性并且特别是杀昆虫活性的稠合二环杂环化合物、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鳞翅目和半翅目的代表)的用途。
杀昆虫活性的稠合二环杂芳香族化合物是例如从以下项已知的:WO 2013/149903、WO 2007/115647、WO 2012/136751、WO 2013/144088、WO 2013/150115、WO 2012/152741和WO 2014/076272。
现在已经发现另外的稠合二环杂芳香族化合物具有杀昆虫特性。
根据本发明,提供了一种具有式(I)的化合物:
其中:
W是O或S;
R1是苯基或萘基,各自任选地:(i)被独立地选自U1a的取代基单取代或多取代,(ii)被独立地选自U1b的取代基单取代或二取代,或(iii)被独立地选自U1a的取代基单取代或二取代,并且被选自U1b的取代基单取代;或者
R1是5-至12-元杂芳香族环体系或3-至12-元饱和的或部分饱和的杂环的环体系,其中所述环体系是单环的或多环的并且包含1至4个选自氮、氧和硫的杂原子,其前提是每个环体系不能含有多于2个氧或硫原子,并且其中每个环体系任选地:(i)被独立地选自U1a的取代基单取代或多取代,(ii)被独立地选自U1b的取代基单取代或二取代,或(iii)被独立地选自U1a的取代基单取代或二取代,并且被选自U1b的取代基单取代;
U1a独立地选自卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基和C1-C6卤代烷氧基;
U1b独立地选自硝基、氰基、氨基、羟基、-SCN、-CO2H、C3-C6环烷基、C3-C6卤代环烷基、C3-C6环烷基-C1-C4烷基、C3-C6卤代环烷基-C1-C4烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基-C1-C4烷氧基、氰基-C1-C4烷基、氰基-C1-C4卤代烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C1-C4卤代烷氧基-C1-C4烷基、C1-C6烷基硫烷基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、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烷基羰基、C1-C6烷氧基羰基、C1-C6卤代烷基羰基、C1-C6卤代烷氧基羰基、(C1-C6烷基)N(H)-、(C1-C6烷基)2N-、(C3-C6环烷基)N(H)-、(C3-C6环烷基)2N-、C1-C6烷基羰基氨基、C3-C6环烷基羰基氨基、C1-C6卤代烷基羰基氨基、C3-C6卤代环烷基羰基氨基、C1-C6烷基氨基羰基、C3-C6环烷基氨基羰基、C1-C6卤代烷基氨基羰基、C3-C6卤代环烷基氨基羰基、C3-C6环烷基羰基、C3-C6卤代环烷基羰基、-SF5、-NHS(O)2C1-C4烷基、甲酰基或-C(O)NH2;或者
U1b是苯基,所述苯基任选地被独立地选自U2的基团单取代或二取代;或者
U1b是5-或6-元杂芳香族环或5-或6-元饱和的或部分饱和的杂环,其中每个环包含1至4个选自氮、氧和硫的杂原子,其前提是每个环不能含有多于2个氧或硫原子,并且其中每个环任选地被独立地选自U2的基团单取代或二取代;
U2是卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、硝基、氰基、氨基、羟基、-SCN、-CO2H、C3-C6环烷基、C3-C6卤代环烷基、C3-C6环烷基-C1-C4烷基、C3-C6卤代环烷基-C1-C4烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基-C1-C4烷氧基、氰基-C1-C4烷基、氰基-C1-C4卤代烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C1-C4卤代烷氧基-C1-C4烷基、C1-C6烷基硫烷基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、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烷基羰基、C1-C6烷氧基羰基、C1-C6卤代烷基羰基、C1-C6卤代烷氧基羰基、-SF5或-C(O)NH2;
m是0、1或2;
R2独立地选自卤素、氰基、氨基、羟基、C1-C6烷基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷氧基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C3-C6环烷基、C3-C6卤代环烷基、C1-C6烷基硫烷基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基硫烷基、C1-C6卤代烷基亚磺酰基和C1-C6卤代烷基磺酰基;
R3a和R3b独立地选自氢、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基和氰基;
R4选自Y1至Y7之一;
其中,n是0、1、2、或3;
Z是氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基;并且
U3独立地选自卤素、氰基、硝基、羟基、氨基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4卤代烷氧基-C1-C4烷基、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、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、甲酰基、环丙基、C1-C6烷基羰基或C3-C6环烷基羰基;
或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物。
出人意料地,已经发现了,为实际目的,具有式(I)的新颖化合物具有非常有利水平的用于保护植物对抗昆虫的生物活性。
根据本发明的第二方面,提供了一种具有式(II)的化合物:
其中m、R2、R3a、R3b和R4对应于与对于具有式(I)的化合物的相同定义,其前提是具有式(II)的化合物不是4-[(6-氯-3-吡啶基)甲基]-1H-咪唑并[4,5-b]吡啶-2-酮。
根据本发明的第三方面,提供了一种农用化学组合物,所述组合物包含杀昆虫、杀螨、杀线虫、或杀软体动物有效量的如根据本发明所定义的具有式(I)的化合物。
根据本发明的第四方面,提供了一种控制昆虫、螨、线虫或软体动物的方法,所述方法包括将杀昆虫、杀螨、杀线虫或杀软体动物有效量的如根据本发明所定义的具有式(I)的化合物、或包含此化合物作为活性成分的组合物施用到有害生物、有害生物场所(优选植物)、易受有害生物攻击的植物或其繁殖材料(如种子)。根据本发明的这个特定方面,所述方法可以不包括通过手术或疗法来治疗人体或动物体的方法。
根据本发明的第五方面,提供了根据式(I)的化合物作为杀昆虫剂、杀螨剂、杀线虫剂或杀软体动物剂的用途。根据本发明的这个特定方面,所述用途可以不包括通过手术或疗法来治疗人体或动物体的方法。
如本文使用的,术语“卤素(halogen或halo)”是指氟(fluorine,fluoro)、氯(chlorine,chloro)、溴(bromine,bromo)或碘(iodine,iodo),优选氟、氯或溴。
如本文使用的,氰基意指-CN基团。
如本文使用的,术语“羟基(hydroxyl)”或“羟基(hydroxy)”意指-OH基团。
如本文使用的,氨基意指-NH2基团。
如本文使用的,硝基意指-NO2基团。
如本文使用的,甲酰基意指-C(O)H基团。
如本文使用的,术语“C1-C6烷基”是指仅由碳原子和氢原子组成的直链或支链的烃链基团,所述烃链基团不含不饱和度,具有从一至六个碳原子,并且其通过单键附接至分子的剩余部分。C1-C4烷基、C1-C3烷基和C1-C2烷基应相应地解释。C1-C6烷基的实例包括但不限于甲基、乙基、正丙基、1-甲基乙基(异丙基)、正丁基和1,1-二甲基乙基(叔丁基)。“C1-C4亚烷基”基团是指C1-C4烷基的相应定义,不同之处在于此种基团是通过两个单键附接至分子的剩余部分。C1-C4亚烷基的实例是-CH2-和-CH2CH2-。
如本文使用的,术语“C1-C6卤代烷基”是指如上一般定义的C1-C6烷基基团,其被一个或多个相同或不同的卤素原子取代。C1-C6卤代烷基的实例包括但不限于氟甲基、氟乙基、二氟甲基、三氟甲基、2,2-二氟乙基、2,2,2-三氟乙基、以及3,3,3-三氟丙基。
如本文使用的,术语“C1-C6烷氧基”是指具有式RaO-的基团,其中Ra是如上一般定义的C1-C6烷基基团。术语“C1-C4烷氧基”应被相应地解释。C1-C6烷氧基的实例包括但不限于甲氧基、乙氧基、丙氧基、异丙氧基和叔丁氧基。
如本文使用的,术语“C1-C6卤代烷氧基”是指如上所定义的C1-C6烷氧基基团,其被一个或多个相同或不同的卤素原子取代。C1-C4卤代烷氧基应相应地解释。C1-C6卤代烷氧基的实例包括但不限于氟甲氧基、二氟甲氧基、氟乙氧基、三氟甲氧基和三氟乙氧基。
如本文使用的,术语“C2-C6烯基”是指仅由碳原子和氢原子组成的直链或支链的烃链基团,所述烃链基团含有至少一个可以是(E)-或(Z)-构型的双键,具有从二至六个碳原子,其通过单键附接至分子的剩余部分。C2-C6烯基的实例包括但不限于丙-1-烯基、烯丙基(丙-2-烯基)和丁-1-烯基。
如本文使用的,术语“C2-C6卤代烯基”是指被一个或多个相同或不同的卤素原子取代的如上一般定义的C2-C6烯基基团。
如本文使用的,术语“C2-C6炔基”是指仅由碳原子和氢原子组成的直链或支链的烃链基团,所述烃链基团包含至少一个三键,具有从二至六个碳原子,并且通过单键附接至分子的剩余部分。C2-C6炔基的实例包括但不限于丙-1-炔基、炔丙基(丙-2-炔基)和丁-1-炔基。
如本文使用的,术语“C2-C6卤代炔基”是指如上一般定义的C2-C6炔基基团,其被一个或多个相同或不同的卤素原子取代。
如本文使用的,术语“C3-C6环烷基”是指稳定的单环基团,其是饱和的或部分不饱和的并且含有3至6个碳原子。C3-C4环烷基应相应地解释。C3-C6环烷基的实例包括但不限于环丙基、环丁基、环戊基、环戊烯-1-基、环戊烯-3-基、以及环己烯-3-基。
如本文使用的,术语“C3-C6环烷基C1-C4烷基”是指通过如上定义的C1-C4亚烷基基团附接至分子的剩余部分的如上定义的C3-C6环烷基环。C3-C6环烷基C1-C4烷基的实例包括但不限于环丙基-甲基、环丁基-乙基、以及环戊基-甲基。
如本文使用的,术语“C3-C6卤代环烷基”是指如上定义的C3-C6环烷基环,其被一个或多个相同或不同的卤素原子取代。
如本文使用的,术语“C3-C6卤代环烷基C1-C4烷基”是指通过如上定义的C1-C4亚烷基基团附接至分子的剩余部分的如上定义的C3-C6卤代环烷基基团。
如本文使用的,术语“C1-C4烷氧基C1-C4烷基”是指具有式Ry-O-Rx-的基团,其中Ry是如上一般定义的C1-C4烷基基团,并且Rx是如上一般定义的C1-C4亚烷基基团。
如本文使用的,术语“C1-C4卤代烷氧基C1-C4烷基”是指具有式Ry-O-Rx-的基团,其中Ry是如上一般定义的C1-C4烷基基团(其被一个或多个相同或不同的卤素原子取代),并且Rx是如上一般定义的C1-C4亚烷基基团。
如本文使用的,术语“C1-C4烷氧基C1-C4烷氧基”是指具有式Ry-O-Rx-O-的基团,其中Ry是如上一般定义的C1-C4烷基基团,并且Rx是如上一般定义的C1-C4亚烷基基团。
如本文使用的,术语“氰基C1-C4烷基”是指如上一般定义的C1-C4烷基基团,其被一个或多个氰基基团取代。氰基C1-C2烷基应相应地解释。
如本文使用的,术语“氰基C1-C4卤代烷基”是指如上一般定义的C1-C6卤代烷基基团,其被一个或多个氰基基团取代。
如本文使用的,术语“C1-C6烷基硫烷基”是指具有式RxS-的基团,其中Rx是如上一般定义的C1-C6烷基基团。
如本文使用的,术语“C1-C6卤代烷基硫烷基”是指如上一般定义的C1-C6烷基硫烷基基团,其被一个或多个相同或不同的卤素原子取代。
如本文使用的,术语“C1-C6烷基亚磺酰基”是指具有式RxS(O)-的基团,其中Rx是如上一般定义的C1-C6烷基基团。
如本文使用的,术语“C1-C6卤代烷基亚磺酰基”是指如上一般定义的C1-C6烷基亚磺酰基基团,其被一个或多个相同或不同的卤素原子取代。
如本文使用的,术语“C1-C6烷基磺酰基”是指具有式RxS(O)2-的基团,其中Rx是如上一般定义的C1-C6烷基基团。
如本文使用的,术语“C1-C6卤代烷基磺酰基”是指如上一般定义的C1-C6烷基磺酰基基团,其被一个或多个相同或不同的卤素原子取代。
如本文使用的,术语“C1-C6烷基羰基”是指具有式RxC(O)-的基团,其中Rx是如上一般定义的C1-C6烷基基团。
如本文使用的,术语“C1-C6卤代烷基羰基”是指如上一般定义的C1-C6烷基羰基基团,其被一个或多个相同或不同的卤素原子取代。
如本文使用的,术语“C1-C6烷氧基羰基”是指具有式RxOC(O)-的基团,其中Rx是如上一般定义的C1-C6烷基基团。
如本文使用的,术语“C1-C6卤代烷氧基羰基”是指如上一般定义的C1-C6烷氧基羰基,其被一个或多个相同或不同的卤素原子取代。
如本文使用的,术语“C1-C6烷基羰基氨基”是指具有式RxC(O)N(H)-的基团,其中Rx是如上一般定义的C1-C6烷基基团。
如本文使用的,术语“C1-C6卤代烷基羰基氨基”是指如上一般定义的C1-C6烷基羰基氨基基团,其被一个或多个相同或不同的卤素原子取代。
如本文使用的,术语“C3-C6环烷基羰基氨基”是指具有式RxC(O)N(H)-的基团,其中Rx是如上一般定义的C3-C6环烷基基团。
如本文使用的,术语“C3-C6卤代环烷基羰基氨基”是指如上一般定义的C3-C6环烷基羰基氨基基团,其被一个或多个相同或不同的卤素原子取代。
如本文使用的,术语“C1-C6烷基氨基羰基”是指具有式RxNHC(O)-的基团,其中Rx是如上一般定义的C1-C6烷基基团。
如本文使用的,术语“C1-C6卤代烷基氨基羰基”是指如上一般定义的C1-C6烷基氨基羰基基团,其被一个或多个相同或不同的卤素原子取代。
如本文使用的,术语“C3-C6环烷基氨基羰基”是指具有式RxNHC(O)-的基团,其中Rx是如上一般定义的C3-C6环烷基基团。
如本文使用的,术语“C3-C6卤代环烷基氨基羰基”是指如上一般定义的C3-C6环烷基氨基羰基基团,其被一个或多个相同或不同的卤素原子取代。
如本文使用的,术语“C3-C6环烷基羰基”是指具有式RxC(O)-的基团,其中Rx是如上一般定义的C3-C6环烷基基团。
如本文使用的,术语“C3-C6卤代环烷基羰基”是指如上一般定义的C3-C6环烷基羰基基团,其被一个或多个相同或不同的卤素原子取代。
5-至12-元杂芳香族环系统(其可以是单环的或多环的并且其包括1至4个选自氮、氧和硫的杂原子)的实例包括吡啶基、嘧啶基、吡咯基、吡唑基、呋喃基、噻吩基、咪唑基、异噁唑基、噁唑基、噻唑基、异噻唑基、三唑基、噁二唑基、噻二唑基、四唑基、吡嗪基、哒嗪基、三嗪基、吡喃基、喹唑啉基、异喹啉基、吲哚嗪基、异苯并呋喃基萘啶基、喹喔啉基、辛尼林基、酞嗪基、苯并噻唑基、苯并噁唑基、苯并三唑基、吲唑基、吲哚基、四氢喹啉基、苯并呋喃基、苯并异呋喃基、苯并噻吩基、苯并异噻吩基、异吲哚基、萘啶基、苯并异噻唑基、苯并异噁唑基、苯并噁唑基、苯并三嗪基、嘌呤基、蝶呤基、吲哚啉基、苯基吡啶基和吡啶基苯基。
3-至12-元饱和的或部分饱和的杂环体系(其可以是单环的或多环的并且包含1至4个选自氮、氧和硫的杂原子)的实例包括二氢吡喃基、四氢呋喃基、四氢噻吩基、吡咯烷基、异噁唑烷基、异噻唑烷基、吡唑烷基、噁唑烷基、噻唑烷基、咪唑烷基、噁二唑烷基、噻二唑烷基、二氢呋喃基、二氢噻吩基、吡咯啉基、异噁唑啉基、二氢吡唑基、二氢噁唑基、哌啶基、二噁烷基、四氢吡喃基、六氢哒嗪基、六氢嘧啶基、环氧乙烷基、以及哌嗪基。
如本文使用的多环的是指稠合环状环,以及取代的环状环,其中取代基是另一个环状环(如芳基或杂芳基环)。稠合环的实例是萘基、苯并异噁唑基或苯并噁唑基,而取代环的实例是联苯基、2-苯基吡啶基或2-吡啶基苯基。
具有至少一个碱性中心的根据本发明的具有式(I)的化合物可以例如与以下形成例如酸加成盐:强无机酸(例如矿物酸,例如高氯酸、硫酸、硝酸、磷酸或氢卤酸),强有机羧酸(例如未经取代的或例如被卤素取代的C1-C4烷羧酸,例如乙酸,例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,例如羟基羧酸,例如抗坏血酸、乳酸、苹果酸、酒石酸或柠檬酸,或例如苯甲酸),或有机磺酸(例如未经取代的或例如被卤素取代的C1-C4烷磺酸或芳基磺酸,例如甲烷磺酸或对甲苯磺酸)。具有至少一个酸性基团的具有式(I)的化合物可以例如与碱形成盐,例如矿物盐,例如碱金属或碱土金属盐,例如钠盐、钾盐或镁盐;或与氨或有机胺形成盐,例如吗啉、哌啶、吡咯烷、单、二或三低碳数烷基胺,例如乙胺、二乙胺、三乙胺或二甲基丙基胺,或单、二或三羟基低碳数烷基胺,例如单乙醇胺、二乙醇胺或三乙醇胺。
在具有式(I)的化合物中一个或多个可能的不对称碳原子的存在意味着所述化合物能以手性异构体形式存在,即对映异构体或非对映异构体的形式。作为围绕单键的受限旋转的结果,还可能存在阻转异构体。式(I)旨在包括所有那些可能的异构体形式及其混合物。本发明包括具有式(I)的化合物的所有那些可能的异构形式及其混合物。同样地,式(I)旨在包括所有可能的互变异构体(包括内酰胺-内酰亚胺互变异构和酮-烯醇互变异构)(当存在时)。本发明包括具有式(I)的化合物的所有可能的互变异构体形式。
在每种情况下,根据本发明的具有式(I)的所述化合物是呈游离形式、氧化形式(作为N-氧化物)、共价水合形式、或盐形式(如农艺学上可用的或农用化学上可接受的盐形式)。N-氧化物是叔胺的氧化形式或含氮杂芳香族化合物的氧化形式。例如,A.Albini和S.Pietra于1991年在博卡拉顿(Boca Raton)CRC出版社出版的名为“Heterocyclic N-oxides[杂环N-氧化物]”一书中描述了它们。根据本发明的具有式(I)的化合物还包括在盐形成期间可以形成的水合物。
以下列表提供了关于本发明的具有式(I)的化合物的取代基W、R1、R2、m、R3a、R3b、R4(即Y1、Y2、Y3、Y4、Y5、Y6、Y7)、U1a、U1b、U2、以及U3和n的定义,包括优选的定义。对于这些取代基中的任何一个,以下给出的任何定义都可以结合以下或在本文件中的其他地方给出的任何其他取代基的任何定义。
W是O或S。优选地,W是O。
R1是苯基或萘基,各自任选地:(i)被独立地选自U1a的取代基单取代或多取代(例如二取代),(ii)被独立地选自U1b的取代基单取代或二取代,或(iii)被独立地选自U1a的取代基单取代或二取代,并且被选自U1b的取代基单取代;或者R1是5-至12-元杂芳香族环体系或3-至12-元饱和的或部分饱和的杂环的环体系,其中所述环体系是单环的或多环的(例如二环的)并且包含1至4个选自氮、氧和硫的杂原子,其前提是每个环体系不能含有多于2个氧或硫原子,并且其中每个环体系任选地:(i)被独立地选自U1a的取代基单取代或多取代(例如二取代),(ii)被独立地选自U1b的取代基单取代或二取代,或(iii)被独立地选自U1a的取代基单取代或二取代,并且被选自U1b的取代基单取代。
在本发明的一些实施例中,R1是苯基,或5-或6-元杂芳香族单环的环体系,所述环体系包含1或2个氮原子或是呋喃基或噻吩基,其中每个R1任选地:
(i)被独立地选自U1a的取代基单取代或多取代(例如二取代的),
(ii)被独立地选自U1b的取代基单取代或二取代,或
(iii)被独立地选自U1a的取代基单取代或二取代,并且被选自U1b的取代基单取代。
在本发明的其他实施例中,R1是苯基、吡唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、噁唑基(1,3-噁唑基)、噁二唑基(1,3,4-噁二唑基)、噻唑基(1,3-噻唑基)、噻二唑基(1,3,4-噻二唑基)、呋喃基或噻吩基,其中每个R1任选地:
(i)被独立地选自U1a的取代基单取代或多取代(例如二取代的),
(ii)被独立地选自U1b的取代基单取代或二取代,或
(iii)被独立地选自U1a的取代基单取代或二取代,并且被选自U1b的取代基单取代。
具体地,R1选自苯基、吡唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、噁唑基(1,3-噁唑基)、噁二唑基(例如1,3,4-噁二唑基)、噻唑基(1,3-噻唑基)、噻二唑基(例如1,3,4-噻二唑基)、呋喃基或噻吩基,其中R1任选地:
(i)被独立地选自U1a的取代基单取代或二取代,其中,U1a是卤素、C1-C4烷基、C1-C4氟烷基、C1-C4烷氧基以及C1-C4氟烷氧基,或
(ii)被选自U1b的取代基单取代,其中,U1b是硝基、氰基、氨基、C3-C6环烷基、氰基C1-C4烷基、C1-C4烷基羰基、C1-C4烷氧基羰基、C1-C4卤代烷基羰基,或苯基或任选地被选自U2的取代基取代的氧杂环丁烷-3-基,其中,U2选自氟、氯、甲基、乙基、甲氧基、乙氧基或三氟甲基。
可替代地,R1选自苯基、吡唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、噁唑基(1,3-噁唑基)、噁二唑基(例如1,3,4-噁二唑基)、噻唑基(1,3-噻唑基)、噻二唑基(例如1,3,4-噻二唑基)、呋喃基或噻吩基,其中R1任选地:
(i)被独立地选自U1a的取代基单取代或二取代,其中,U1a选自卤素、C1-C4烷基、二氟甲基、三氟甲基、甲氧基、乙氧基以及三氟甲氧基,或
(ii)被选自U1b的取代基单取代,其中,U1b是硝基、氰基、氨基、C3-C6环烷基、氰基甲基、甲基羰基、乙基羰基、甲氧基羰基、乙氧基羰基、三氟甲基羰基,或苯基或氧杂环丁烷-3-基。
R1可以是苯基、吡唑-3-基、吡唑-4-基、吡啶-2-基、吡啶-3-基、吡啶-4-基、嘧啶-2-基、嘧啶-4-基、嘧啶-5-基、哒嗪-3-基、吡嗪-2-基、噁唑-2-基、1,3,4-噁二唑-2-基、噻唑-2-基、噻唑-4-基、噻唑-5-基、1,3,4-噻二唑-2-基、呋喃-2-基、呋喃-3-基、噻吩-2-基或噻吩-3-基,其中,每个R1任选地:
(i)被独立地选自U1a的取代基单取代或二取代,其中,U1a是卤素、C1-C4烷基、C1-C4氟烷基、C1-C4烷氧基以及C1-C4氟烷氧基,或
(ii)被选自U1b的取代基单取代,其中,U1b是硝基、氰基、氨基、C3-C6环烷基、氰基C1-C4烷基、C1-C4烷基羰基、C1-C4烷氧基羰基、C1-C4卤代烷基羰基,或苯基或任选地被选自U2的取代基取代的氧杂环丁烷-3-基,其中,U2选自氟、氯、甲基、乙基、甲氧基、乙氧基或三氟甲基。
可替代地,R1可以是苯基、吡唑-3-基、吡唑-4-基、吡啶-2-基、吡啶-3-基、吡啶-4-基、嘧啶-2-基、嘧啶-4-基、嘧啶-5-基、哒嗪-3-基、吡嗪-2-基、噁唑-2-基、1,3,4-噁二唑-2-基、噻唑-2-基、噻唑-4-基、噻唑-5-基、1,3,4-噻二唑-2-基、呋喃-2-基、呋喃-3-基、噻吩-2-基或噻吩-3-基,其中,每个R1任选地:
(i)被独立地选自U1a的取代基单取代或二取代,其中,U1a选自卤素、C1-C4烷基、二氟甲基、三氟甲基、甲氧基、乙氧基以及三氟甲氧基,或
(ii)被选自U1b的取代基单取代,其中,U1b是硝基、氰基、氨基、C3-C6环烷基、氰基甲基、甲基羰基、乙基羰基、甲氧基羰基、乙氧基羰基、三氟甲基羰基,或苯基或氧杂环丁烷-3-基。
在本发明的还其他实施例中,R1是苯基、吡唑基、吡啶基、嘧啶基、哒嗪基或吡嗪基、其中,每个R1任选地:
(i)被独立地选自U1a的取代基单取代或多取代(例如二取代的),
(ii)被独立地选自U1b的取代基单取代或二取代,或
(iii)被独立地选自U1a的取代基单取代或二取代,并且被选自U1b的取代基单取代。
当R1任选地被苯基、吡唑基、吡啶基、嘧啶基、哒嗪基或吡嗪基取代时,这可以包括任选地被取代的吡唑-3-基、吡唑-4-基、吡啶-2-基、吡啶-3-基、吡啶-4-基、嘧啶-2-基、嘧啶-4-基、嘧啶-5-基、哒嗪-3-基、哒嗪-4-基、以及吡嗪-2-基。
优选地,R1是苯基,或5-或6-元杂芳香族单环的环体系,所述环体系包含1或2个氮原子,并且其中每个R1任选地被以下取代:
(i)独立地选自U1a的1或2个取代基,其中,U1a是卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基以及C1-C4卤代烷氧基,或
(ii)选自U1b的1个取代基,其中,U1b是氰基或任选地被选自U2的1个取代基取代的苯基,其中,U2是氟、氯、甲基、三氟甲基、甲氧基或氰基。
更优选地,R1是苯基、吡唑基、吡啶基、嘧啶基、哒嗪基或吡嗪基,其中,每个R1任选地被以下取代:
(i)独立地选自U1a的1或2个取代基,其中,U1a是卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基以及C1-C4卤代烷氧基,或
(ii)选自U1b的1个取代基,其中,U1b是氰基或任选地被选自U2的1个取代基取代的苯基,其中,U2是氟、氯、甲基、三氟甲基、甲氧基或氰基。
甚至更优选地,R1是苯基、吡唑基、吡啶基、嘧啶基、哒嗪基或吡嗪基,其中,每个R1任选地被以下取代:
(i)独立地选自U1a的1或2个取代基,其中,U1a是氟、氯、甲基、乙基、正丙基、异丙基、二氟甲基、三氟甲基、甲氧基、乙氧基以及三氟甲氧基,或
(ii)选自U1b的1个取代基,其中,U1b是氰基或苯基。
在其他实施例中,R1是吡唑基,所述吡唑基任选地被独立地选自U1a的1或2个取代基(其中U1a是C1-C4烷基或C1-C4卤代烷基),或选自U1b的单个取代基(其中U1b是C3-C6环烷基)取代。
优选地,R1是吡唑基,所述吡唑基任选地被独立地选自U1a的1或2个取代基(其中U1a是C1-C4烷基或C1-C4氟烷基),或选自U1b的单个取代基(其中U1b是C3-C4环烷基)取代。
更优选地,R1是任选地被独立地选自U1a的1或2个取代基(其中U1a是甲基、乙基、正丙基、异丙基、二氟甲基以及三氟甲基),或选自U1b的单个取代基(其中U1b是环丙基)取代的吡唑基(具体地,吡唑-4-基)。
U1a独立地选自卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基以及C1-C6卤代烷氧基。
U1b独立地选自硝基、氰基、氨基、羟基、-SCN、-CO2H、C3-C6环烷基、C3-C6卤代环烷基、C3-C6环烷基-C1-C4烷基、C3-C6卤代环烷基-C1-C4烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基-C1-C4烷氧基、氰基-C1-C4烷基、氰基-C1-C4卤代烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C1-C4卤代烷氧基-C1-C4烷基、C1-C6烷基硫烷基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、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烷基羰基、C1-C6烷氧基羰基、C1-C6卤代烷基羰基、C1-C6卤代烷氧基羰基、(C1-C6烷基)N(H)-、(C1-C6烷基)2N-、(C3-C6环烷基)N(H)-、(C3-C6环烷基)2N-、C1-C6烷基羰基氨基、C3-C6环烷基羰基氨基、C1-C6卤代烷基羰基氨基、C3-C6卤代环烷基羰基氨基、C1-C6烷基氨基羰基、C3-C6环烷基氨基羰基、C1-C6卤代烷基氨基羰基、C3-C6卤代环烷基氨基羰基、C3-C6环烷基羰基、C3-C6卤代环烷基羰基、-SF5、-NHS(O)2C1-C4烷基、甲酰基或-C(O)NH2;或者
U1b是苯基,所述苯基任选地被独立地选自U2的基团单取代或二取代;或者
U1b是5-或6-元杂芳香族环或5-或6-元饱和的或部分饱和的杂环,其中每个环包含1至4个选自氮、氧和硫的杂原子,其前提是每个环不能含有多于2个氧或硫原子,并且其中每个环任选地被独立地选自U2的基团单取代或二取代。
优选地,U1a选自卤素、C1-C4烷基、C1-C4氟烷基、C1-C4烷氧基和C1-C4氟烷氧基。更优选地,U1a选自卤素、甲基、乙基、正丙基、异丙基、C1-C2氟烷基、甲氧基、乙氧基以及C1-C2氟烷氧基。最优选地,U1a选自氟、氯、甲基、乙基、正丙基、异丙基、二氟甲基、三氟甲基、甲氧基、乙氧基以及三氟甲氧基。
优选地,U1b选自氰基或苯基,所述苯基任选地被选自U2的1个取代基取代。
U2是卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、硝基、氰基、氨基、羟基、-SCN、-CO2H、C3-C6环烷基、C3-C6卤代环烷基、C3-C6环烷基-C1-C4烷基、C3-C6卤代环烷基-C1-C4烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基-C1-C4烷氧基、氰基-C1-C4烷基、氰基-C1-C4卤代烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C1-C4卤代烷氧基-C1-C4烷基、C1-C6烷基硫烷基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、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烷基羰基、C1-C6烷氧基羰基、C1-C6卤代烷基羰基、C1-C6卤代烷氧基羰基、-SF5或-C(O)NH2。优选地,U2选自氯、氟、甲基、乙基、甲氧基、氰基和三氟甲基。
m是0、1或2。在本发明的一些实施例中,m是0。在本发明的一些实施例中,m是1(例如根据式(I-1b))。在本发明的一些实施例中,m是2。优选地,m是0或1,并且更优选地,m是0。
R2独立地选自卤素、氰基、氨基、羟基、C1-C6烷基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷氧基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C3-C6环烷基、C3-C6卤代环烷基、C1-C6烷基硫烷基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基硫烷基、C1-C6卤代烷基亚磺酰基和C1-C6卤代烷基磺酰基。
优选地,R2独立地选自卤素、氰基、氨基、羟基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C2-C4卤代炔基、C3-C4环烷基、C3-C4卤代环烷基、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基和C1-C4卤代烷基磺酰基。更优选地,R2独立地选自卤素、氰基、氨基、羟基、C1-C4烷基、C1-C4氟烷基、C1-C4氟烷氧基、C1-C4烷氧基、C2-C4烯基、C2-C4氟烯基、C2-C4炔基、C2-C4氟炔基、C3-C4环烷基和C3-C4氟环烷基。甚至更优选地,R2独立地选自氟、氯、甲基、乙基、三氟甲基、三氟甲氧基、甲氧基或乙氧基。还更优选地,R2是甲基,具体地,当n是1时。
R3a和R3b独立地选自氢、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基和氰基。优选地,R3a是氢并且R3b选自氢、氯、氟、甲基、乙基、三氟甲基、2,2-二氟乙基、2,2,2-三氟乙基、甲氧基或乙氧基。更优选地,R3a是氢并且R3b是氢或甲基。最优选地,R3a是氢并且R3b是氢。
R4选自Y1至Y7之一;
其中,n是0、1、2、或3。
优选地,n是0或1。
Z是氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基。
优选地,Z是氢、甲基、乙基或三氟甲基。更优选地,Z是氢或甲基。
U3独立地选自卤素、氰基、硝基、羟基、氨基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4卤代烷氧基-C1-C4烷基、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、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、甲酰基、环丙基、C1-C6烷基羰基或C3-C6环烷基羰基。
优选地,U3独立地选自卤素、氰基、硝基、羟基、氨基、C1-C4烷基、C1-C4氟烷基、C1-C4烷氧基、C1-C4氟烷氧基、C1-C2氟烷氧基-C1-C2烷基、C1-C2烷氧基-C1-C2烷基、C1-C4烷基硫烷基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4氟烷基硫烷基、C1-C4氟烷基亚磺酰基、C1-C4氟烷基磺酰基、甲酰基、环丙基、C1-C4烷基羰基或C3-C6环烷基羰基。更优选地,U3独立地选自卤素、氰基、硝基、羟基、氨基、甲基、乙基、三氟甲基、甲氧基、乙氧基。最优选地,U3独立地选自氟、氯和三氟甲基,并且特别是氯。
在本发明的一些优选实施例中,R4选自Y2、Y3或Y4之一。
在本发明的一些优选实施例中,R4选自以下项之一:
在本发明的一些优选实施例中,R4选自以下项之一:
在本发明的一些优选实施例中,R4选自以下项之一:
在本发明的某些实施例中,具有式(I)的化合物是:
其中,R1是根据本发明定义的,并且X代表氢或R2为甲基。
在本发明的某些实施例中,具有式(I)的化合物是:
其中,R1是根据本发明定义的,并且X代表氢或R2为甲基。
在本发明的某些实施例中,具有式(I)的化合物是:
其中,R1是根据本发明定义的,并且X代表氢或R2为甲基。
优选地,根据式(I)的化合物选自表1(下文)中列出的化合物1.001至1.105或表A(下文)中列出的化合物A1至A102。
在一些实施例中,在本发明的根据式(I)的化合物中:
W是O;
R1是苯基、吡唑基、吡啶基、嘧啶基、哒嗪基或吡嗪基,其中,每个R1任选地:(i)被独立地选自U1a的取代基单取代或二取代,(ii)被独立地选自U1b的取代基单取代或二取代,或(iii)被独立地选自U1a的取代基单取代或二取代,并且被选自U1b的取代基单取代;
U1a是卤素、甲基、乙基、正丙基、异丙基、C1-C2氟烷基、甲氧基、乙氧基以及C1-C2氟烷氧基;
U1b选自氰基或苯基,所述苯基任选地被选自U2的1个取代基取代,其中,U2是氯、氟、甲基、乙基、甲氧基、氰基以及三氟甲基;
R2是甲基;
m是0或1;
R3a和R3b独立地选自氢和甲基;并且
R4选自:
在其他实施例中,
W是O;
R1是苯基、吡唑基、吡啶基、嘧啶基、哒嗪基或吡嗪基,其中,每个R1任选地:(i)被独立地选自U1a的取代基单取代或二取代,(ii)被独立地选自U1b的取代基单取代或二取代,或(iii)被独立地选自U1a的取代基单取代或二取代,并且被选自U1b的取代基单取代;
U1a是氟、氯、甲基、乙基、正丙基、异丙基、二氟甲基、三氟甲基、甲氧基、乙氧基以及三氟甲氧基;
U1b选自氰基或苯基,所述苯基任选地被选自U2的1个取代基取代,其中,U2是氯、氟、甲基、乙基、甲氧基、氰基以及三氟甲基;
m是0;
R3a和R3b独立地选自氢和甲基;并且
R4选自:
在还其他实施例中,
W是O;
R1是苯基、吡唑基、吡啶基、嘧啶基、哒嗪基或吡嗪基,其中,每个R1任选地:(i)被独立地选自U1a的取代基单取代或二取代,(ii)被独立地选自U1b的取代基单取代或二取代,或(iii)被独立地选自U1a的取代基单取代或二取代,并且被选自U1b的取代基单取代;
U1a是氟、氯、甲基、乙基、正丙基、异丙基、二氟甲基、三氟甲基、甲氧基、乙氧基以及三氟甲氧基;
U1b选自氰基或苯基,所述苯基任选地被选自U2的1个取代基取代,其中,U2是氯、氟、甲基、乙基、甲氧基、氰基以及三氟甲基;
m是0;
R3a和R3b是氢;并且
R4是:
对于m、R2、R3a、R3b和R4,具有式(II)的化合物具有如对于具有式(I)的化合物以及它们的相应优选物相同的定义。
在具有式(II)的化合物中,优选地,m是0或1,并且更优选地,m是0。
在具有式(II)的化合物中,当m是1时,优选地,R2是C1-C4烷基,并且更优选甲基。
在具有式(II)的化合物中,优选地,R3a和R3b是氢。
在具有式(II)的化合物中,优选地,R4选自以下项之一:
,并且更优选地,
根据本发明,具有式(II)的化合物可以不包括化合物,其中m是0,R3a和R3b是氢并且R4是6-氯-吡啶-3-基基团(即4-[(6-氯-3-吡啶基)甲基]-1H-咪唑并[4,5-b]吡啶-2-酮)。
本发明的化合物可以如在以下方案1至6中所示来制备,其中(除非另外说明)每一变量的定义是如本文针对具有式(I)的化合物所定义的。
具有式(Ia)的化合物可以容易地制备,其中,R1、R2、R3a、R3b、R4和m如本文所定义。这种合成的典型实例在以下方案1中示出。
方案1
具有式(Ia)的化合物(其中R1是芳基或杂芳基)可以由具有式(II)的化合物(其中R2、R3a、R3b、R4和m如对于式(I)所定义),在碱、铜催化剂和配体的存在下,通过与具有式R1-LG的化合物(其中LG是离去基团,如碘离子或溴离子)金属催化偶联来制备。这种类型的偶联(称为乌尔曼型偶联反应)是本领域技术人员熟知的,参见例如,Chem.Rev.[化学评论]2004,248,第2337-2364页;Tetrahedron[四面体]2011,67(29),第5282-5288页;Angew.Chem.,Int.Ed.[应用化学国际版]2003,42,第5400-5449页;Synlett[合成快报]2003,第2428-2439页;Ind.Eng.Chem.Res.[工业与工程化学研究]2005,44,第789-798页。所述反应通常用一至两当量的碱(如磷酸钾)在铜催化剂(例如像碘化铜(I))的存在下并且在含氧气氛下进行。所述反应可以在惰性溶剂(如二噁烷或甲苯)中,通常在50℃至150℃之间的温度下并且在或不在另外的配体(例如像二胺配体(例如N,N’-二甲基乙二胺),二苯亚甲基丙酮(dba)和1,10-菲咯啉)的存在下进行。
可替代地,具有式(Ia)的化合物(其中R1是芳基或杂芳基)可以由具有式(II)的化合物(其中R2、R3a、R3b、R4和m如以上对于式(I)所定义),通过Buchwald-Hartwig交叉偶联来制备,Buchwald-Hartwig交叉偶联包括例如,使具有式R1-LG的化合物(其中LG是离去基团,例如氯离子、碘离子或溴离子,或芳基磺酸根或烷基磺酸根,如三氟甲磺酸根)与例如具有式(II)的化合物反应。所述反应可以通过钯基催化剂(例如乙酸钯),在碱(如碳酸铯或叔丁醇钠)的存在下,在溶剂或溶剂混合物(例如像甲苯)中,优选地在惰性气氛下并且在螯合磷化氢(如2,2′-双(二苯基膦基)-1,1′-联萘(BINAP)或Xantphos)的存在下催化。反应温度的范围可以优先地是从环境温度到反应混合物的沸点。此类Buchwald-Hartwig交叉偶联反应是本领域技术人员熟知的,在文献中描述了其许多变化并且已经综述于以下文献中,Strategic Applications of Named Reactions in Organic Synthesis[有机合成中命名反应的战略性应用](Kurti,Laszlo;Czako,Barbara;编者Ed.ELSEVIER)2005,第70页和其中所引用的参考文献;Modern Tools for the Synthesis of Complex BioactiveMolecules(Chapter 3:Metal-catalyzed C-heteroatom cross-coupling reactions)[用于合成复杂生物活性分子的现代工具(第3章:金属催化的C-杂原子交叉偶联反应]2012,第77-109页。
可替代地,具有式(Ia)的化合物(其中R1是芳基或杂芳基)可以由具有式(II)的化合物(其中R2、R3a、R3b、R4和m如对于式(I)所定义),通过与具有式R1-LG的化合物(其中LG是硼酸官能团或硼酸根或三氟硼酸根基团)进行Chan-Lam偶联来制备。所述反应可以在铜源(如碘化铜(I)或乙酸铜(II))的存在下,任选地在合适的碱(如吡啶或磷酸钾)的存在下进行。所述反应可以在合适的溶剂(如二氯甲烷、二噁烷或二甲亚砜)中,在20℃与180℃之间的温度下在微波辐射或不在微波辐射下,优选地在氧气气氛(如果铜盐以亚化学计量的量使用)下进行。参见例如Tetrahedron Letters[四面体通讯]2015,56(33),第4843-4847页;或RSC Advances[RSC前沿]2013,3(29),第11472-11475页。
具有式(II)的化合物(其中R2、R3a、R3b、R4和m根据本发明所定义)通常是已知的或可以由本领域技术人员容易地制备。这种合成的典型实例在方案2中示出。
方案2
例如,具有式(II)的化合物(其中R2、R3a、R3b、R4和m如对于式(I)所定义),可以通过具有式(III)的化合物与具有式(IV)的化合物(其中LG是离去基团,例如像卤化物)之间的反应来制备,所述反应是如下进行:在或不在合适的碱(例如像碳酸钠、碳酸钾或碳酸铯,或醇锂、醇钠或醇钾)的存在下,在合适的溶剂(其可以包括例如,乙腈、DMF、1,4-二噁烷)中,并且通常在室温与200℃之间,并且优选在20℃至反应混合物的沸点之间的温度下任选地在微波加热条件下将所述反应混合物加热。在所述反应中可以使用催化剂,包括碘化钠或碘化叔丁基铵。
可替代地,具有式(II)的化合物(其中R2、R3a、R3b、R4和m如对于式(I)所定义)可以通过具有式(V)的化合物和具有式(VI)的化合物的反应来制备,其中,LG1和LG2彼此独立地是离去基团,例如像卤化物、芳氧基基团或咪唑基。所述反应可以在0℃至溶剂的沸点下并且优选地在碱的存在下进行,所述碱可以是例如吡啶、胡宁氏碱(Hünig’s base)、三乙胺或碳酸钠。此类方法先前已经描述于以下文献中,例如J Med Chem[药物化学杂志]2015,58,第8066页;J.Het.Chem.[杂环化学期刊]2010,47,第683页;Synth.Comm.[合成通讯]1982,12,第213页。
具有式(III)的化合物是可商购的或可以由本领域技术人员容易地制备。可以在文献中发现许多实例,例如参见Mendeleev Communications[门捷列夫通讯]2016,26(1),第69-71页和其中所引用的参考文献;Bulletin of the Chemical Society of Japan[日本化学学会公报]1987,60(5),第1793-9页;Journal of Heterocyclic Chemistry[杂环化学杂志]1985,22(4),第1061-4页;Heterocycles[杂环](2002),57(12),第2335-2343页。可替代地,具有式(III)的化合物可以如方案2中所描述的制备。具有式(III)的化合物(其中R2和m如对于式(I)所定义)可以是可商购的,或者可以通过库尔修斯重排由可商购的具有式(X)的化合物(其中R2和m是如对于式(I)所描述的),通过用叠氮化磷酸二苯酯(DPPA),在合适的碱(例如像三甲胺)的存在下,在合适的溶剂(其可以包括例如,乙醇、叔丁醇、1,4-二噁烷、四氢呋喃)中,通常在室温与200℃之间,并且优选在20℃至反应混合物的沸点之间的温度下加热处理来制备。这种合成先前已经描述于,例如Journal of MedicinalChemistry[医药化学杂志],58(20),8066-8096;2015中。可替代地,可以使用除了具有式(X)的化合物以外的其他化合物,例如像3-氨基吡啶甲酸的类似物。
具有式(V)的化合物(其中R2、R3a、R3b、R4和m如对于本发明所定义)通常是已知的或可以由本领域技术人员容易地制备。这种合成的典型实例在方案3中示出。
方案3
例如,具有式(V)的化合物(其中R2、R3a、R3b、R4和m如对于式(I)所定义)可以通过具有式(IX)的化合物水解来制备,所述水解是通过如下进行:用合适的强酸(例如像37%浓缩的HCl水溶液),通常在室温与200℃之间,并且优选在20℃至反应混合物的沸点之间的温度下并且任选地在微波加热条件下加热。
可替代地,具有式(V)的化合物(其中R2、R3a、R3b、R4和m如对于式(I)所定义)可以通过具有式(VIII)的化合物水解来制备,所述水解是通过如下进行:用合适的强酸(例如像37%浓缩的HBr水溶液),通常在室温与200℃之间,优选在20℃至反应混合物的沸点之间的温度下并且任选地在微波加热条件下加热。
具有式(IX)的化合物(其中R2、R3a、R3b、R4和m如对于式(I)所定义)可以通过具有式(VIII)的化合物的水解来制备,所述水解通过以下进行:用合适的酸(例如像三氟乙酸(TFA)),在合适的溶剂(其可以包括例如,二氯甲烷或1,2-二氯乙烷)中,并且通常在室温与200℃之间,优选在20℃至反应混合物的沸点之间的温度下任选地在微波加热条件下加热处理。
具有式(VIII)的化合物(其中R2、R3a、R3b、R4和m如对于式(I)所定义),可以通过具有式(VII)的化合物与具有式(IV)的化合物(其中LG是离去基团,例如像卤化物)之间的反应来制备,所述反应是如下进行:在或不在合适的碱(例如像碳酸钠、碳酸钾或碳酸铯,或醇锂、醇钠或醋酸钾)的存在下,在合适的溶剂(其可以包括例如,乙腈、DMF、1,4-二噁烷)中,并且通常在室温与200℃之间,优选在20℃至反应混合物的沸点之间的温度下并且任选地在微波加热条件下加热。在所述反应中可以使用催化剂,包括碘化钠或碘化叔丁基铵。
具有式(VII)的化合物(其中R2和m如对于本发明所定义)通常是已知的或可以由本领域技术人员容易地制备。这种合成的典型实例在方案4中示出。
方案4
例如,具有式(VII)的化合物(其中R2和m如对于式(I)所定义)可以由具有式(XII)的化合物,通过用例如二碳酸二叔丁酯((Boc)2O),在合适的溶剂(其可以包括例如,二氯甲烷、1,2-二氯甲烷、四氢呋喃)中处理,或通过在熔融的二碳酸二叔丁酯中,通常在室温与200℃之间,优选在20℃至反应混合物的沸点之间的温度下加热进行反应来制备。可以使用可替代的保护基团,例如像苯基。具有式(XII)的化合物可以通过具有式(XI)的化合物与具有式(XIII)的化合物的反应来制备,其中,LG1和LG2彼此独立地是离去基团,例如像氨基、卤离子或咪唑。所述反应可以在0℃至溶剂的沸点下并且优选地在碱的存在下进行,所述碱可以是例如吡啶、胡宁氏碱(Hünig’s base)、三乙胺或碳酸钠。此类方法先前已经描述于Eur.J.Med.Chem.[欧洲医药化学杂志]2016,113,第102页中。具有式(XI)的化合物是可商购的或可以由本领域技术人员容易地制备。
可替代地,从具有式(XIV)的化合物制备具有式(Ia)的化合物(其中R1、R2、R3a、R3b和R4是如以上在式(I)下所描述的)的顺序可以涉及:
(i)具有式(XIV)的化合物(其中LG是离去基团,如氟离子或溴离子)与具有式(XVIII)的化合物进行卤素置换,以形成具有式(XV)的化合物。所述反应可以通过LG(例如氟离子)的亲核置换或通过金属催化(如通过Buchwald-Hartwig交叉偶联)进行。LG的亲核置换在碱性条件下,如使用碳酸钾在溶剂(如DMF)中,在从环境温度至反应混合物的沸点下发生。所述Buchwald-Hartwig交叉偶联反应可以通过钯基催化剂(例如乙酸钯),在碱(例如碳酸铯或叔丁醇钠)的存在下,在溶剂(例如甲苯)或溶剂混合物中,并且优选地在惰性气氛下,在螯合磷化氢(如BINAP或Xantphos)的存在下催化。反应温度的范围可以优先地是从环境温度到反应混合物的沸点。此类Buchwald-Hartwig交叉偶联反应是本领域技术人员熟知的。在文献中描述了许多变化并且已经综述于以下文献中,Strategic Applications ofNamed Reactions in Organic Synthesis[有机合成中命名反应的战略性应用](Kurti,Laszlo;Czako,Barbara;编者Ed.ELSEVIER)2005,第70页和其中所引用的参考文献;ModernTools for the Synthesis of Complex Bioactive Molecules(Chapter 3:Metal-catalyzed C-heteroatom cross-coupling reactions)[用于合成复杂生物活性分子的现代工具(第3章:金属催化的C-杂原子交叉偶联反应]2012,第77-109页。可替代地,交叉偶联反应可以由铜催化剂和配体催化。这种类型的偶联被称为乌尔曼型偶联反应并且描述于方案1中。
(ii)经由经典条件还原硝基衍生物(XV),以产生具有式(XVI)的化合物,参见例如Synthetic Organic Methodology:Comprehensive Organic Transformations[有机合成方法:综合有机转换].A Guide to Functional Group Preparations[功能组准备指南],Larock,R.C.1989,第411页。对于参考文献描述的实例的步骤(i)和/或(ii),参见WO 2011/123751、WO 2017/178819或European Journal of Organic Chemistry[欧洲有机化学杂志](22),3753-3764,S3753/1-S3753/35;2009;
(iii)通过与方案2中描述的方法类似的过程,使具有式(XVI)的化合物与具有式(VI)的化合物反应,以产生具有式(XVII)的化合物;以及
(iv)通过类似于方案2中描述的方法,用具有式(IV)的化合物将具有式(XVII)的化合物的吡啶基片段烷基化,以产生具有式(Ia)的化合物。
参见方案5。
方案5
可替代地,从具有式(XVI)的化合物制备具有式(Ia)的化合物(其中R1、R2、R3a、R3b和R4是如以上在式(I)下所描述的)的顺序可以涉及:
(i)通过类似于方案2中描述的方法,用具有式(IV)的化合物将具有式(XVI)的化合物的吡啶基片段烷基化,以产生具有式(XIX)的化合物。
(ii)具有式(XIX)的化合物(其中R1、R2、m、R3a、R3b和R4是如对于式(I)所描述的)与具有式X-CN(XX)的化合物(其中X是卤素,如溴)的至少两种等价物反应,以得到具有式(XXI)的化合物。所述反应在或不在碱(如三乙胺或氢化钠)的存在下,在或不在催化剂(如4-二甲基氨基吡啶)的存在下,在适当的溶剂(例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺或乙腈)中或不存在溶剂,在-78℃与150℃之间,并且优选地在0℃与150℃之间的温度下发生。类似物反应是本领域技术人员熟知的并且可以使用类似的条件,例如参见EP 0 427526;European Journal of Medicinal Chemistry[欧洲医药化学杂志](1993),28(7-8),633-6或WO 2017/005673。
(iii)具有式(XXI)的化合物(其中R1、R2、R3a、R3b和R4是如以上在式(I)下所描述的)在酸性条件(如盐酸)下,在溶剂(如水或水和醇(例如乙醇)的混合物)中,在-20℃至回流之间的温度下进行水解,以得到具有式(Ia)的化合物。参见方案6。
方案6
根据方案1至6任一个中所述的反应,适合的碱的实例可以包括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、二异丙基氨基锂、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-二甲基胺、N,N-二乙基苯胺、吡啶、4-(N,N-二甲基氨基)吡啶、奎宁环、N-甲基吗啉、苄基三甲基氢氧化铵和1,8-二氮杂二环[5.4.0]十一碳-7-烯(DBU)。
反应物可以原样相互反应,即不添加溶剂或稀释剂。然而,在大多数情况下,添加惰性溶剂或稀释剂或这些物质的混合物是有利的。如果反应在碱存在下进行,则过量使用的碱如三乙胺、吡啶、N-甲基吗啉或N,N-二乙基苯胺也可用作溶剂或稀释剂。
反应有利地在从约-80℃到约140℃、优选从约-30℃到约100℃的温度范围内,在许多情况下在环境温度与约80℃之间的范围内进行。
具有式(I)的化合物能以本身已知的方式转化为另一种具有式(I)的化合物,这是通过以常规方式将具有式(I)的起始化合物的一个或多个取代基用根据本发明的另一个或其他一个或多个取代基的替代来实现的。
取决于所选的适合各自情况的反应条件以及起始材料,有可能例如,在一个反应步骤中仅将一个取代基用根据本发明的另一个取代基替代,或者在同一个反应步骤中可以将多个取代基用多个根据本发明的其他取代基来替代。
具有式(I)的化合物的盐能以本身已知的方式来制备。因此,例如,具有式(I)的化合物的酸加成盐是通过用适合的酸或合适的离子交换试剂进行处理来获得的,并且与碱的盐是通过用适合的碱或用合适的离子交换试剂进行处理来获得的。
具有式(I)的化合物的盐能以常规方式转化为游离的化合物(I)、酸加成盐(例如通过用适合的碱性化合物或用适合的离子交换剂试剂进行处理)以及与碱的盐(例如通过用适合的酸或用适合的离子交换剂试剂进行处理)。
具有式(I)的化合物的盐能以本身已知的方式转化为具有式(I)的化合物的其他盐、酸加成盐,例如转化成其他酸加成盐,例如通过在适合的溶剂中用酸的适合的金属盐(诸如钠、钡或银的盐,例如用乙酸银)来处理无机酸的盐(诸如盐酸盐),在所述溶剂中,所形成的无机盐(例如氯化银)是不溶的并且因此从所述反应混合物中沉淀出。
取决于程序或反应条件,具有成盐特性的这些具有式(I)的化合物能以游离形式或盐的形式获得。
具有化学式(I)的化合物和适当时其互变异构体(在每种情况下呈游离形式或呈盐形式)能够以可能的异构体之一的形式或以这些异构体的混合物的形式,例如以纯异构体(如对映体和/或非对映异构体)形式或以异构体混合物(如对映异构体混合物,例如外消旋体;非对映异构体混合物或外消旋体混合物)形式存在,取决于分子中存在的不对称碳原子的数目、绝对和相对构型和/或取决于分子中存在的非芳香族双键的构型;本发明涉及纯异构体以及还有可能的所有异构体混合物,并且在上下文的每种情况下,甚至在没有具体提及立体化学细节的每种情况下,都应该从这层意义上来理解。
呈游离形式或呈盐形式的具有式(I)的化合物的非对映异构体混合物或外消旋体混合物(它们的获得可以取决于已选定的起始材料和程序)能够在这些组分的物理化学差异的基础上,例如通过分步结晶、蒸馏和/或色谱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(诸如外消旋体)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色谱法,例如在乙酰纤维素上的高效液相色谱法(HPLC);借助于适合的微生物,通过用特异性固定化酶裂解;通过形成包含化合物,例如使用手性冠醚,其中仅一个对映异构体被络合;或通过转化成非对映异构体的盐,例如通过使碱性最终产物外消旋体与光学活性酸(诸如羧酸,例如樟脑酸、酒石酸或苹果酸,或磺酸,例如樟脑磺酸)反应,并且分离能够以此方式获得的非对映异构体混合物,例如基于其不同溶解度通过分步结晶,从而获得非对映异构体,从所述非对映异构体可以通过适合的试剂(例如碱性试剂)的作用使所希望的对映异构体变成游离的。
纯的非对映异构体或对映异构体能根据本发明来获得,不仅是通过分离适合的异构体混合物,还可以是通过普遍已知的非对映立体选择性或对映选择性合成的方法,例如通过根据本发明用具有适合的立体化学的起始材料进行所述方法。
如果单个组分具有不同的生物活性,有利的是在每一情况下分离或合成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。
根据本发明的具有式(I)的化合物在有害生物控制领域中是有预防和/或治疗价值的活性成分,即使是在低的施用量下,它们具有非常有利的杀生物谱并且可以是温血物种、鱼以及植物良好耐受的。具有式(I)的化合物可以具有针对非目标物种(如蜜蜂)的有益的安全性,以及因此良好的毒性特征曲线。根据本发明的这些活性成分可以作用于正常敏感的而且还有抗性有害生物(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)发生对有害生物的破坏;或间接显示,例如降低产卵和/或孵化率。
上述有害生物的实例是:
来自蜱螨目,例如
下毛瘿螨属(Acalitus spp.)、针刺瘿螨属、窄瘿螨属(Acaricalus spp.)、瘤瘿螨属(Aceria spp.)、粗脚粉螨、钝眼蜱属、锐缘蜱属、牛蜱属、短须螨属、、上三节瘿螨属(Calipitrimerus spp.)、皮螨属、鸡皮刺螨、表皮螨属、始叶螨属、瘿螨属、半跗线螨属、璃眼蜱属、硬蜱属、小爪螨属、钝缘蜱属、侧多食跗线螨、全爪螨属、桔芸锈螨、植食螨(Phytonemus spp.)、跗线螨属、痒螨属、扇头蜱属、根嗜螨属、疥螨属、狭跗线螨属、跗线属以及叶螨属;
来自虱目,例如
血虱属(Haematopinus spp.)、长颚虱属(Linognathus spp.)、人虱(Pediculusspp.)、天疱疮属(Pemphigus spp.)以及木虱(Phylloxera spp.);
来自鞘翅目,例如
缺隆叩甲属、Amphimallon majale、东方异丽金龟、花象属、蜉金龟属、Astylusatromaculatus、Ataenius spp、Atomaria linearis、甜菜胫跳甲、萤叶甲属(Cerotomaspp)、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、Diloboderus abderus、食植瓢虫属、Eremnus spp.、黑异爪蔗金龟、咖啡果小蠹、Lagriavilosa、马铃薯甲虫、稻水象属、Liogenys spp、Maecolaspis spp、栗色绒金龟、Megascelisspp、Melighetes aeneus、金龟属、Myochrous armatus、锯谷盗属、耳喙象属(Otiorhynchusspp.)、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 spp、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、花园毛蚊、迟眼蕈蚊属、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、Geomyzatripunctata、舌蝇属、皮蝇属、虱蝇属、斑潜蝇属、绿蝇属、潜蝇属(Melanagromyza spp.)、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、Riveliaquadrifasciata、Scatella spp.、蕈蚊属、刺蝇属、虻属、绦虫属以及大蚊属,
来自半翅目,例如
瘤缘蝽(Acanthocoris scabrator)、绿蝽属、苜蓿盲蝽、Amblypeltanitida、海虾盾缘蝽(Bathycoelia thalassina)、土长蝽属、臭虫属、Clavigralla tomentosicollis、盲蝽属(Creontiades spp.)、可可瘤盲蝽、Dichelops furcatus、棉红蝽属、Edessa spp.、美洲蝽属(Euchistus spp.)、六斑菜蝽(Eurydema pulchrum)、扁盾蝽属、美洲蝽属(Euschistus spp.)(椿象(stinkbug))、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(Murgantia histrionic)、Neomegalotomusspp.、烟盲蝽(Nesidiocoris tenuis)、绿蝽属、拟长蝽(Nysius simulans)、Oebalusinsularis、皮蝽属、壁蝽属、红猎蝽属、可可盲蝽象、Scaptocoris castanea、黑蝽属(Scotinophara spp.)、Thyanta spp.、锥鼻虫属、木薯网蝽(Vatiga illudens)、
无网长管蚜属、Adalges spp.、Agalliana ensigera、Agonoscena targionii、粉虱属(Aleurodicus spp.)、Aleurocanthus spp.、甘蔗穴粉虱、软毛粉虱(Aleurothrixusfloccosus)、甘蓝粉虱(Aleyrodes brassicae)、棉叶蝉(Amarasca biguttula)、Amritodusatkinson、肾圆盾蚧属、蚜科、蚜属、蚧属(Aspidiotus spp.)、茄沟无网蚜、Bactericeracockerelli、小粉虱属、Brachycaudus spp.、甘蓝蚜、喀木虱属、双尾蚜(Cavariellaaegopodii Scop.)、蜡蚧属、褐圆蚧、网籽草叶圆蚧、Cicadella spp.、大白叶蝉(Cofanaspectra)、隐瘤蚜属、Cicadulina spp.、褐软蚧、玉米黄翅叶蝉、裸粉虱属、柑橘木虱、麦双尾蚜、西圆尾蚜属、小绿叶蝉属、苹果绵蚜、葡萄斑叶蝉属、蜡蛤属、赤桉木虱(Glycaspisbrimblecombei)、菜缢管蚜、Hyalopterus spp.、超瘤蚜种、檬果绿叶蝉(Idioscopusclypealis)、Jacobiasca lybica、灰飞虱属、球坚蚧、蛎盾蚧属、萝卜蚜(Lopaphiserysimi)、Lyogenys maidis、长管蚜属、Mahanarva spp.、蛾蜡蝉科(Metcalfa pruinosa)、麦无网蚜、Myndus crudus、瘤蚜属、台湾韭蚜、黑尾叶蝉属、褐飞虱属(Nilaparvata spp.)、梨大绿蚜、Odonaspis ruthae、寄生甘蔗绵蚜、杨梅缘粉虱、考氏木虱、片盾蚧属、瘿绵蚜属、玉米蜡蝉、扁角飞虱属、忽布疣蚜、根瘤蚜属、动性球菌属、白盾蚧属、粉蚧属、棉盲蝽(Pseudatomoscelis seriatus)、木虱属、棉蚧(Pulvinaria aethiopica)、笠圆盾蚧属、Quesada gigas、电光叶蝉(Recilia dorsalis)、缢管蚜属、黑盔蚧属、带叶蝉属、二叉蚜属、麦蚜属(Sitobion spp.)、白背飞虱、Spissistilus festinus、条斑飞虱(TarophagusProserpina)、声蚜属、粉虱属、Tridiscus sporoboli、葵粉蚧属(Trionymus spp.)、非洲木虱、桔矢尖蚧、Zygina flammigera、Zyginidia scutellaris,
来自膜翅目,例如
顶切叶蚁属、三节属(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)、实叶蜂属、毛蚁属、小黄家蚁、新松叶蜂属、收获蚁属、Slenopsis invicta、水蚁属和胡蜂属;
来自等翅目,例如
家白蚁属、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(Lepidoptera),例如,
长翅卷蛾属、褐带卷蛾属、透翅蛾属、地夜蛾属、棉叶虫、Amylois spp.、黎豆夜蛾、黄卷蛾属、Argyresthia spp.、带卷蛾属、丫纹夜蛾属、棉潜蛾、玉米楷夜蛾、粉斑螟蛾、桃小食心虫、禾草螟属、卷叶蛾属、Chrysoteuchia topiaria、葡萄果蠹蛾、卷叶螟属、云卷蛾属、纹卷蛾属、鞘蛾属、篱笆豆粉蝶、Cosmophila flava、草螟属(Crambus spp.)、大菜螟、苹果异形小卷蛾、Cydalima perspectalis、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、小卷蛾属、顶灯蛾、Etiella zinckinella、花小卷蛾属、环针单纹蛾、黄毒蛾属、切根虫属、Feltia jaculiferia、小食心虫属(Grapholita spp)、绿青虫蛾、实夜蛾属、菜心螟、Herpetogramma spp.、美国白蛾、番茄蠹蛾、Lasmopalpus lignosellus、旋纹潜叶蛾、潜叶细蛾属、葡萄花翅小卷蛾、Loxostege bifidalis、毒蛾属、潜蛾属、幕枯叶蛾属、甘蓝夜蛾、烟草天蛾、Mythimna spp.、夜蛾属、秋尺蛾属、Orniodes indica、欧洲玉米螟、超小卷蛾属、褐卷蛾属、小眼夜蛾、蛀茎夜蛾、Pectinophora gossypiela、咖啡潜叶蛾、一星黏虫、马铃薯块茎蛾、菜粉蝶、粉蝶属、菜蛾属、芽蛾属、尺夜蛾属、Rachiplusia nu、Richia albicosta、白禾螟属、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(Mallophaga),例如,
畜虱属(Damalinea spp.)和啮毛虱属(Trichodectes spp.);
来自直翅目(Orthoptera),例如,
蠊属、小蠊属、蝼蛄属、马德拉蜚蠊、飞蝗属、北痣蟋蟀、大蠊属、痣蟋蟀属以及沙漠蝗属,
来自啮虫目(Psocoptera),例如,
虱啮属(Liposcelis spp.),
来自蚤目(Siphonaptera),例如,
角叶蚤属(Ceratophyllus spp.)、栉头蚤属(Ctenocephalides spp.)以及开皇客蚤(Xenopsylla cheopis),
来自缨翅目(Thysanoptera),例如,
Calliothrips phaseoli、花蓟马属、阳蓟马属、褐带蓟马属、Parthenothripsspp.、南非柑桔蓟马、大豆蓟马、带蓟马属、蓟马属;
来自缨尾目(Thysanura),例如,衣鱼(Lepisma saccharina)。
根据本发明的活性成分可用于控制、也就是遏制或破坏上述类型的有害生物,这些有害生物特别出现在植物上,尤其是在农业中、在园艺中以及在林业中的有用的植物和观赏植物上,或者在这些植物的器官上,例如果实、花、叶、茎、块茎或根,并且在一些情况下,甚至在一个随后的时间点形成的植物器官仍保持受保护以抵抗这些有害生物。
适合的目标作物具体是谷物,如小麦、大麦、黑麦、燕麦、水稻、玉米或高粱;甜菜,例如糖用甜菜或饲料甜菜;水果,例如苹果类水果、核果类水果或无核水果,例如苹果、梨、李子、桃、杏仁、樱桃或浆果,例如草莓、覆盆子或黑莓;豆科作物,例如蚕豆、小扁豆、豌豆或大豆;油料作物,例如油菜、芥菜、罂粟、橄榄、向日葵、椰子、蓖麻、可可或落花生;葫芦,例如南瓜、黄瓜或甜瓜;纤维植物,例如棉花、亚麻、大麻或黄麻;柑桔类水果,例如橙子、柠檬、葡萄柚或橘子;蔬菜,例如菠菜、莴苣、芦笋、甘蓝、胡萝卜、洋葱、蕃茄、马铃薯或铃状椒;樟科植物,例如鳄梨、肉桂或樟脑;以及还有烟草、坚果、咖啡、茄子、甘蔗、茶叶、胡椒、葡萄树、蛇麻子、车前科、产胶植物以及观赏植物。
根据本发明的这些活性成分可能尤其适合于控制棉花、蔬菜、玉米、水稻以及大豆作物上的豆蚜、黄瓜条叶甲、烟蓟马、大豆褐椿(Euschistus heros)、烟芽夜蛾、桃蚜、小菜蛾以及海灰翅夜蛾。根据本发明所述的活性成分另外尤其适合于控制甘蓝夜蛾(Mamestra)(优选地在蔬菜上)、苹果蠹蛾(Cydia pomonella)(优选地在苹果上)、小绿叶蝉(Empoasca)(优选地在蔬菜、葡萄园里)、马铃薯叶甲(Leptinotarsa)(优选地在马铃薯上)以及二化螟(Chilo supressalis)(优选地在水稻上)。
在另一个方面,本发明还可以涉及控制由植物寄生的线虫(内寄生的-、半内寄生的-以及外寄生的线虫)对植物或其部分引起损害的方法,尤其是以下植物寄生的线虫,如根结线虫(root knot nematodes)、北方根结线虫(Meloidogyne hapla)、南方根结线虫(Meloidogyne incognita)、爪哇根结线虫(Meloidogyne javanica)、花生根结线虫(Meloidogyne arenaria)以及其他根结线虫属种类(Meloidogyne species);孢囊形成线虫(cyst-forming nematodes)、马铃薯金线虫(Globodera rostochiensis)以及其他球孢囊线虫属种类(Globodera species);禾谷孢囊线虫(Heterodera avenae)、大豆胞囊线虫(Heterodera glycines)、甜菜胞囊线虫(Heterodera schachtii)、红三叶异皮线虫(Heterodera trifolii)、以及其他异皮线虫属种类(Heterodera species);种瘿线虫(Seed gall nematodes)、粒线虫属种类(Anguina species);茎及叶面线虫(Stem andfoliar nematodes)、滑刃线虫属种类(Aphelenchoides species);刺毛线虫(Stingnematodes)、长尾刺线虫(Belonolaimus longicaudatus)以及其他刺线虫属种类;松树线虫(Pine nematodes)、松材线虫(Bursaphelenchus xylophilus)以及其他伞滑刃属种类(Bursaphelenchus species);环形线虫(Ring nematodes)、环线虫属种类(Criconemaspecies)、小环线虫属种类(Criconemella species)、轮线虫属种类(Criconemoidesspecies)、中环线虫属种类(Mesocriconema species);茎及鳞球茎线虫(Stem and bulbnematodes)、腐烂茎线虫(Ditylenchus destructor)、鳞球茎茎线虫(Ditylenchusdipsaci)以及其他茎线虫属种类(Ditylenchus species);锥线虫(Awl nematodes)、锥线虫属种类(Dolichodorus species);螺旋线虫(Spiral nematodes)、多头螺旋线虫(Heliocotylenchus multicinctus)以及其他螺旋线虫属种类(Helicotylenchusspecies);鞘及鞘形线虫(Sheath and sheathoid nematodes)、鞘线虫属种类(Hemicycliophora species)以及半轮线虫属种类(Hemicriconemoides species);潜根线虫属种类(Hirshmanniella species);支线虫(Lance nematodes)、冠线虫属种类(Hoploaimus species);假根结线虫(false rootknot nematodes)、珍珠线虫属种类(Nacobbus species);针状线虫(Needle nematodes)、横带长针线虫(Longidoruselongatus)以及其他长针线虫属种类(Longidorus species);大头针线虫(Pinnematodes)、短体线虫属种类(Pratylenchus species);腐线虫(Lesion nematodes)、花斑短体线虫(Pratylenchus neglectus)、穿刺短体线虫(Pratylenchus penetrans)、弯曲短体线虫(Pratylenchus curvitatus)、古氏短体线虫(Pratylenchus goodeyi)以及其他短体线虫属种类(Pratylenchus species);柑桔穿孔线虫(Burrowing nematodes)、香蕉穿孔线虫(Radopholus similis)以及其他内侵线虫属种类(Radopholus species);肾形线虫(Reniform nematodes)、罗柏氏盘旋线虫(Rotylenchus robustus)、肾形盘旋线虫(Rotylenchus reniformis)以及其他盘旋线虫属种类(Rotylenchus species);盾线虫属种类(Scutellonema species);短粗根线虫(Stubby root nematodes)、原始毛刺线虫(Trichodorus primitivus)以及其他毛刺线虫属种类(Trichodorus species)、拟毛刺线虫属种类(Paratrichodorus species);矮化线虫(Stunt nematodes)、马齿苋矮化线虫(Tylenchorhynchus claytoni)、顺逆矮化线虫(Tylenchorhynchus dubius)以及其他矮化线虫属种类(Tylenchorhynchus species);柑桔线虫(Citrus nematodes)、穿刺线虫属种类(Tylenchulus species);短剑线虫(Dagger nematodes)、剑线虫属种类(Xiphinemaspecies);以及其他植物寄生的线虫种类,如亚粒线虫属(Subanguina spp.)、Hypsoperine属、大刺环线虫属(Macroposthonia spp.)、Melinius属、刻点胞囊属(Punctodera spp.)、以及五沟线虫属(Quinisulcius spp.)。
本发明所述的化合物还具有针对软体动物的活性。这些软体动物的实例包括,例如苹果螺科;阿勇蛞蝓属(Arion)(灰黑阿勇蛞蝓(A.ater)、环斑阿勇蛞蝓(A.circumscriptus)、庭院阿勇蛞蝓(A.hortensis)、红棕阿勇蛞蝓(A.rufus));巴蜗牛科(灌木巴蜗牛(Bradybaena fruticum));蜗牛属(庭院蜗牛(C.hortensis),森林蜗牛(C.nemoralis));ochlodina;灰蛞蝓属(Deroceras)(野灰蛞蝓(D.agrestis)、D.empiricorum、田灰蛞蝓(D.laeve)、庭园灰蛞蝓(D.reticulatum));圆盘螺属(Discus)(D.rotundatus);Euomphalia;土蜗属(Galba)(截形土蜗(G.trunculata));小蜗牛属(Helicelia)(伊塔拉小蜗牛(H.itala)、布维小蜗牛(H.obvia));大蜗牛科Helicigonaarbustorum);Helicodiscus;大蜗牛属(Helix)(开放大蜗牛(H.aperta));蛞蝓属(Limax)(灰黑蛞蝓(L.cinereoniger)、黄蛞蝓(L.flavus),边缘蛞蝓(L.marginatus),大蛞蝓(L.maximus),柔蛞蝓(L.tenellus));椎实螺属(Lymnaea);Milax(M.gagates、M.marginatus、M.sowerbyi);钻螺属(Opeas);瓶螺属(Pomacea)(P.canaticulata);瓦娄蜗牛属(Vallonia)和Zanitoides。
根据式(I)的化合物可以在控制先前对杀有害生物(杀昆虫)剂的新烟碱种类(“新烟碱类”)敏感的昆虫的抗性群体中找到实用性。因此,本发明可以涉及一种控制对新烟碱杀昆虫剂有抗性的昆虫的方法,所述方法包括将具有式(I)的化合物(例如选自表1(下文)中列出的化合物1.001至1.105或表A(下文)列出的化合物A1至A102的单一化合物)施用至新烟碱抗性的昆虫。同样地,本发明可以涉及具有式(I)的化合物(例如选自表1(下文)中列出的化合物1.001至1.105或表A(下文)列出的化合物A1至A102的单一化合物)作为针对新烟碱抗性的昆虫的杀昆虫剂的用途。此类新烟碱抗性的昆虫可以包括来自鳞翅目或半翅目、特别是来自蚜科的昆虫。
新烟碱类代表自拟除虫菊酯商业化以来引进市场的熟知的一类杀昆虫剂(Nauen&Denholm,2005:Archives of Insect Biochemistry and Physiology[昆虫生物化学与生理学文献]58:200-215),并且是极有价值的昆虫控制剂,尤其是因为它们对老的杀虫剂类别展现出很少或没有交叉抗性,这些老的杀虫剂类别明显地遭受抗性问题。然而,关于昆虫对新烟碱类杀虫剂的抗性的报道正在增多。
因此,这类昆虫对新烟碱杀昆虫剂的抗性增强对许多重要经济作物、水果和蔬菜的种植构成了重大威胁,并且因此需要找到能够控制新烟碱抗性昆虫的替代杀昆虫剂(即,找到未展现出任何与新烟碱类的交叉抗性的杀昆虫剂)。
抗性可以定义为“有害生物群体的敏感度的可遗传变化,所述可遗传变化反映在当根据对所述有害生物物种的标签建议使用时,实现所希望水平的控制的含杀昆虫活性成分的产品的重复失败中”(IRAC)。当对一种杀昆虫剂的抗性通过相同的生物化学机理赋予对另外一种杀昆虫剂的抗性时交叉抗性发生。这可以发生在杀虫剂化学品的组之内或在杀虫剂化学品的组之间。即使所述具有抗性的昆虫从来没有暴露于杀虫剂的化学品类别之一中,交叉抗性仍可以发生。
对于新烟碱抗性的主要机制中的两个包括:-
(i)靶标位点抗性,借此抗性与杀虫剂靶标蛋白质(即烟碱乙酰胆碱受体)中的一个或多个氨基酸的置换相关联;以及
(ii)代谢抗性,例如因过表达单加氧酶而对新烟碱的氧化解毒增强;
关于对新烟碱杀昆虫剂的昆虫抗性的一般综述参见例如PesticideBiochemistry and Physiology[杀有害生物剂生物化学与生理学](2015),121,78-87或Advances in Experimental Medicine and Biology[实验医学和生物学的进展](2010),683(Insect Nicotinic乙酰基choline Receptors[昆虫烟碱乙酰胆碱受体]),75-83。
细胞色素P450单加氧酶是参与解毒/活化异型生物质的重要的代谢系统。这样,P450单加氧酶在杀虫剂抗性中起重要作用。P450单加氧酶具有如此惊人的一系列可代谢底物,这是因为在每个物种中存在众多P450(60-111)并且一些P450的底物特异性较宽范。单加氧酶-介导的抗性的研究已经表明抗性可以归因于参与杀昆虫剂解毒的一种P450的增加的表达(经由增加的转录),并且还可能归因于结构基因本身的变化。这样,代谢交叉抗性机制不仅影响来自给定类别的杀虫剂(例如新烟碱),而且影响看似不相关的杀虫剂。例如,在烟粉虱中在新烟碱与吡蚜酮之间的交叉抗性关系已经由Gorman等人(Pest ManagementScience[有害生物管理科学]2010,1186-1190页)报道。或例如,关于通过P450解毒的证据参见例如Harrop,Thomas WR等人Pest Management Science[有害生物管理科学](2018),74(7),p1616-1622以及引用的参考文献。
对烟碱的靶标位点抗性进行了充分研究,并且已经示出烟碱乙酰胆碱受体的修饰活性位点赋予对烟碱的抗性。例如,参见Bass等人BMC Neuroscience[BMC神经系统科学](2011),12,p 51,Pest Management Science[有害生物管理科学](2018),74(6),1297-1301,
术语“作物”应当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,这些毒素是如已知例如来自于产毒素细菌,尤其是芽孢杆菌属的那些细菌。
可通过所述转基因植物表达的毒素包括,例如杀昆虫蛋白质,例如杀昆虫蛋白质,例如来自于枯草芽孢杆菌或日本甲虫芽孢杆菌的杀昆虫蛋白质;或来自于苏云金芽孢杆菌的杀昆虫蛋白质,例如δ-内毒素,例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C,或营养期杀昆虫蛋白(Vip),例如Vip1、Vip2、Vip3或Vip3A;或线虫寄生性细菌的杀昆虫蛋白质,例如光杆状菌属或致病杆菌属,例如发光光杆状菌、嗜线虫致病杆菌;由动物产生的毒素,例如蝎毒素、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,例如链霉菌毒素;植物凝集素,例如豌豆凝集素、大麦凝集素或雪花莲凝集素;凝集素类;蛋白酶抑制剂,例如胰蛋白酶抑制剂、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),例如蓖麻蛋白、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,例如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,例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结构域的新组合重组产生的(参见例如,WO 02/15701)。截短的毒素,例如截短的Cry1Ab是已知的。在经修饰的毒素的情况下,天然存在的毒素的一个或多个氨基酸被置换。在这种氨基酸置换中,优选将非天然存在的蛋白酶识别序列插入毒素中,例如在Cry3A055的情况下,一种组织蛋白酶-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。
用于制备此类转基因植物的方法通常是本领域技术人员已知的并且描述在例如以上提及的公开物中。CryI型脱氧核糖核酸及其制备例如从WO 95/34656、EP-A-0 367474、EP-A-0 401 979和WO 90/13651中已知。
包括在转基因植物中的毒素使得植物对有害昆虫有耐受性。这样的昆虫可以存在于任何昆虫分类群,但尤其常见于甲虫(鞘翅目)、双翅昆虫(双翅目)和蛾(鳞翅目)。
包含一种或多种编码杀昆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。此类植物的实例是:(玉米品种,表达Cry1Ab毒素);YieldGard Rootworm(玉米品种,表达Cry3Bb1毒素);YieldGard(玉米品种,表达Cry1Ab以及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);NewLeaf(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
此类转基因作物的另外的实例是:
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玉米还转基因表达PAT酶以获得对除草剂草铵膦铵盐的耐受性。
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玉米还转基因表达酶PAT以获得对除草剂草铵膦铵盐的耐受性。
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,比利时,登记号C/DE/02/9。MON 863表达Cry3Bb1毒素,并且对某些鞘翅目昆虫有抗性。
5.IPC 531棉花,来自孟山都欧洲公司(Monsanto Europe S.A.),270-272特弗伦大道(Avenue de Tervuren),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蛋白质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(Monsanto Europe S.A.),270-272特弗伦大道(Avenue de Tervuren),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×MON810玉米转基因地表达由土壤杆菌属菌株CP4获得的蛋白质CP4 EPSPS,使之耐除草剂(含有草甘膦),以及由苏云金芽孢杆菌库尔斯塔克亚种获得的Cry1Ab毒素,使之耐某些鳞翅目昆虫,包括欧洲玉米螟。
抗昆虫的植物的转基因作物还描述于BATS(生物安全与可持续发展中心(Zentrumfür Biosicherheit und Nachhaltigkeit),BATS中心(Zentrum BATS),克拉斯崔舍(Clarastrasse)13,巴塞尔(Basel)4058,瑞士)报告2003(http://bats.ch)中。
术语“作物”应理解为还包括已经通过使用重组DNA技术而被这样转化使其能够合成具有选择性作用的抗病原物质的作物植物,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)。这样的抗病原物质和能够合成这样的抗病原物质的转基因植物的实例例如从EP-A-0 392 225、WO 95/33818和EP-A-0 353 191是已知的。生产这样的转基因植物的方法对于本领域的普通技术人员而言通常是已知的并且描述于例如以上提及的公开物中。
作物也可以经修饰以增加对真菌(例如镰孢霉属、炭疽病或疫霉属)、细菌(例如假单胞菌属)或病毒(例如马铃薯卷叶病毒、番茄斑萎病毒、黄瓜花叶病毒)病原体的抗性。
作物还包括那些对线虫(如大豆异皮线虫)具有增加的抗性的作物。
具有对非生物性胁迫的耐受性的作物包括那些例如通过NF-YB或本领域中已知的其他蛋白质的表达对干旱、高盐、高温、寒冷、霜或光辐射具有增加的耐受性的作物。
可以由此类转基因植物表达的抗病原物质包括例如离子通道阻断剂(如钠和钙通道阻断剂,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);由微生物产生的抗病原物质,例如参与植物病原体防御的肽抗生素或杂环类抗生素(参见例如WO 95/33818)或蛋白质或多肽因子(所谓的“植物疾病抗性基因”,如描述于WO 03/000906中)。
根据本发明的组合物的其他使用范围是保护所储存的物品和储藏环境以及保护原材料,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的侵害。
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,通过本发明的方法考虑到了表面(诸如墙、天花板或地板表面)的IRS(室内滞留喷雾)施用。在另一个实施例中,考虑到了将此类组合物施用于如下基底,诸如无纺或织物材料,所述材料处于网织品、被覆物、被褥、窗帘以及帐篷的形式(或可以用于在这些物品的制造中使用)。本发明的另外的目的因此是选自包含含有具有式I的化合物的组合物的无纺和织物材料的基质。
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,以便于在所述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,通过本发明的方法考虑到了表面(诸如墙、天花板或地板表面)的IRS施用,以便于在所述表面上提供有效的滞留的杀有害生物活性。在另一个实施例中,考虑了施用这样的组合物以用于在基底上的有害生物的残留控制,所述基底是诸如处于网织品、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。
有待处理的基质(包括无纺物、织物或网织品)可以由天然纤维,诸如棉花、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,诸如聚酰胺、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、WO03/034823、US 5631072、WO 2005/64072、WO 2006/128870、EP 1724392、WO 2005113886或WO 2007/090739。
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尤其适合于对抗来自如上提及的鳞翅目和来自鞘翅目的蛀木昆虫,尤其是对抗下表中列出的蛀木虫:
具有经济重要性的外来蛀木虫的实例。
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 pearl)、千足虫、潮虫、螨虫、蝼蛄、介壳虫、粉蚧蜱、沫蝉、南方麦小蝽以及蛴螬。本发明可以用于控制处于其生命周期的各个阶段的昆虫有害生物,包括卵、幼虫、若虫和成虫。
具体而言,本发明可用于控制用草坪草的根部喂养的昆虫有害生物,所述昆虫有害生物包括蛴螬(诸如圆头犀金龟属(Cyclocephala spp.)(例如标记的金龟子、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(Phyllophagaspp.)(例如五月/六月甲虫)、Ataenius属(例如草坪草黑金龟(Black turfgrassataenius)、A.spretulus)、绒毛金龟属(Maladera spp.)(例如亚洲花园甲虫(Asiaticgarden 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 cranefly)、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(诸如秋夜蛾(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.),诸如S.venatus verstitus和牧草长喙象(S.parvulus))以及草地螟(如草螟属(Crambusspp.)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(诸如南方麦小蝽,南方杆长蝽(Blissus insularis))、狗牙根螨(Bermudagrass mite)(Eriophyes cynodoniensis)、盖氏虎尾草粉蚧(草竹粉蚧(Antonina graminis))、两线沫蝉(Propsapia bicincta)、叶蝉、切根虫(夜蛾科)、以及麦二叉蚜。
本发明还可以用于控制草坪草中的其他有害生物,诸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诸如硬蜱、软蜱、疥螨、秋螨、蝇(叮咬和舔舐)、寄生性蝇幼虫,虱、发虱、鸟虱和跳蚤。
此类寄生虫的实例是:
虱目:血虱属、长腭虱属、人虱属以及阴虱属(Phtirus spp.)、管虱属,
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(Felicola spp.),
双翅目及长角亚目(Nematocerina)和短角亚目(Brachycerina),例如伊蚊属、疟蚊属、库蚊属、蚋属(Simulium spp.)、真蚋属(Eusimulium spp.)、白蛉属(Phlebotomusspp.)、罗蛉属(Lutzomyia spp.)、库蠓属(Culicoides spp.)、斑虻属(Chrysops spp.)、驼背虻属(Hybomitra spp.)、黄虻属(Atylotus spp.)、虻属、麻虻属(Haematopota spp.)、Philipomyia属、蜂虱蝇属(Braula spp.)、家蝇属、齿股蝇属(Hydrotaea spp.)、螫蝇属、黑角蝇属(Haematobia spp.)、莫蝇属(Morellia spp.)、厕蝇属、舌蝇属、丽蝇属(Calliphoraspp.)、绿蝇属、金蝇属、污蝇属(Wohlfahrtia spp.)、麻蝇属(Sarcophaga spp.)、狂蝇属、皮蝇属、胃蝇属(Gasterophilus spp.)、虱蝇属(Hippobosca spp.)、羊虱蝇属(Lipoptenaspp.)和蜱蝇属(Melophagus spp.),
蚤目(Siphonapterida),例如蚤属(Pulex spp.)、栉头蚤属、客蚤属(Xenopsyllaspp.)、角叶蚤属,
异翅目(Heteropterida),例如臭虫属、锥鼻虫属属、红猎蝽属、锥蝽属(Panstrongylus spp.),
蜚蠊目(Blattarida),例如东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta americana)、德国小蠊(Blattelagermanica)以及夏柏拉蟑螂属(Supellaspp.),
蜱螨(Acaria)亚纲(螨科(Acarida))和后气门目(Meta-stigmata)和中气门目(Meso-stigmata),例如锐缘蜱属、钝缘蜱属(Ornithodorus spp.)、耳蜱属(Otobiusspp.)、硬蜱属、钝眼蜱属、牛蜱属(Boophilus spp.)、革蜱属(Dermacentor spp.)、血蜱属(Haemophysalis spp.)、璃眼蜱属、扇头蜱属、皮刺螨属(Dermanyssus spp.)、刺利螨属(Raillietia spp.)、肺刺螨属(Pneumonyssus spp.)、胸刺螨属(Sternostoma spp.)和瓦螨属(Varroa spp.),
轴螨目(Actinedida)(前气门亚目(Prostigmata))和粉螨目(Acaridida)(无气门亚目(Astigmata)),例如蜂盾螨属(Acarapis spp.)、姬螯属(Cheyletiella spp.)、禽螯螨属(Ornithocheyletia spp.)、肉螨属(Myobia spp.)、疮螨属(Psorergates spp.)、蠕形螨属(Demodex spp.)、恙螨属(Trombicula spp.)、牦螨属(Listrophorus spp.)、粉螨属(Acarus spp.)、食酪螨属(Tyrophagus spp.)、嗜木螨属(Caloglyphus spp.)、颈下螨属(Hypodectes spp.)、翅螨属(Pterolichus spp.)、痒螨属、皮螨属、耳疥螨属(Otodectesspp.)、疥螨属、耳螨属(Notoedres spp.)、鸟疥螨属(Knemidocoptes spp.)、胞螨属(Cytodites spp.)以及鸡雏螨属(Laminosioptes spp.)。
根据本发明的组合物还适用于保护材料诸如木材、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。
根据本发明的这些组合物可用于,例如,对抗下列有害生物:甲虫,如北美家天牛、多毛绿虎天牛、家具窃蠹、报死窃蠹、Ptilinuspecticornis、Dendrobium pertinex、细齿叉尾长蠹、Priobium carpini、褐粉蠹、非洲粉蠹、南方粉蠹、抱扁蠹、软毛粉蠹、扁腿粉蠹、鳞毛粉蠹、材小蠹属、木小蠹属、黑长蠹、红腹槲长蠹、棕异翅长蠹、双棘长蠢属以及竹蠹,并且还有膜翅目,如蓝黑树蜂、大树蜂、泰加大树蜂和Urocerus augu,以及白蚁类,如黄颈木白蚁、麻头堆砂白蚁、印巴结构木异白蚁、黄肢散白蚁、桑特散白蚁、欧洲散白蚁、达氏澳白蚁、内华达动白蚁和台湾家白蚁,以及无翼昆虫类,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或添加剂(诸如载体、溶剂以及表面活性物质)被配制成组合物。这些配制品可以处于不同的实体形式,例如,处于以下形式:撒粉剂、凝胶、可湿性粉剂、水可分散性颗粒剂、水可分散性片剂、泡腾压缩片剂、可乳化的浓缩物、微可乳化浓缩物、水包油乳剂、可流动油、水性分散体、油性分散体、悬乳剂、胶囊悬浮液、可乳化的颗粒剂、可溶性液体、水可溶性浓缩物(以水或水混溶性有机溶剂作为载体)、浸渍的聚合物膜或处于已知的其他形式,例如从关于杀有害生物剂的FAO和WHO标准的发展和使用的手册(Manual onDevelopment and Use of FAO and WHO Specifications for Pesticides),联合国,第1版,二次修订(2010)中已知的。此类配制品可以直接使用或者可以在使用前稀释。可以用例如水、液体肥料、微量营养素、生物有机体、油或溶剂来稀释。
可以通过例如将活性成分与配制品佐剂混合来制备这些配制品以便获得处于精细分散固体、颗粒、溶液、分散体或乳剂形式的组合物。这些活性成分还可以与其他佐剂(例如精细分散固体、矿物油、植物或动物的油、改性的植物或动物的油、有机溶剂、水、表面活性物质或它们的组合)来一起配制。
这些活性成分还可以被包含于非常精细的微胶囊中。微胶囊在多孔载体中含有活性成分。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到500微米的直径。它们包含的活性成分的量按重量计是胶囊重量的约从25%至95%。这些活性成分可以处于整体性的固体的形式、处于固体或液体分散体中的精细颗粒的形式或处于合适溶液的形式。包囊的膜可以包括例如天然的或合成的橡胶,纤维素、苯乙烯/丁二烯共聚物、聚丙烯腈、聚丙烯酸酯、聚酯、聚酰胺、聚脲、聚氨酯或化学改性的聚合物以及淀粉黄原酸酯、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这些组合物的配制品佐剂本身是已知的。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、二丙酮醇、1,2-二氯丙烷、二乙醇胺、对-二乙基苯、二甘醇、松脂酸二乙二醇酯、二甘醇丁基醚、二甘醇乙基醚、二甘醇甲醚、N,N-二甲基甲酰胺、二甲基亚砜、1,4-二噁烷、二丙二醇、二丙二醇甲基醚、双丙甘醇二苯甲酸酯、二丙二醇、烷基吡咯烷酮、乙酸乙酯、2-乙基己醇、碳酸乙烯酯、1,1,1-三氯乙烷、2-庚酮、α-蒎烯、d-苧烯、乳酸乙酯、乙二醇、乙二醇丁基醚、乙二醇甲基醚、γ-丁内酯、丙三醇、乙酸甘油酯、二乙酸甘油酯、三乙酸甘油酯、十六烷、己二醇、乙酸异戊基酯、乙酸异冰片基酯、异辛烷、异佛尔酮、异丙苯、肉豆蔻酸异丙酯、乳酸、月桂胺、异亚丙基丙酮、甲氧基丙醇、甲基异戊基酮、甲基异丁基酮、月桂酸甲酯、辛酸甲酯、油酸甲酯、二氯甲烷、间二甲苯、正己烷、正辛胺、十八烷酸、辛胺乙酸酯、油酸、油烯基胺、邻二甲苯、苯酚、聚乙二醇、丙酸、乳酸丙酯、碳酸亚丙酯、丙二醇、丙二醇甲基醚、对-二甲苯、甲苯、磷酸三乙酯、三乙二醇、二甲苯磺酸、石蜡、矿物油、三氯乙烯、全氯乙烯、乙酸乙酯、乙酸戊酯、乙酸丁酯、丙二醇甲基醚、二乙二醇甲基醚、甲醇、乙醇、异丙醇以及更高分子量的醇,例如戊醇、四氢呋喃醇、己醇、辛醇、乙二醇、丙二醇、甘油、N-甲基-2-吡咯烷酮等。
适合的固体载体是例如滑石、二氧化钛、叶蜡石黏土、硅石、凹凸棒石黏土、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、木质素和类似的物质。
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。典型的表面活性剂包括,例如,烷基硫酸盐,比如二乙醇铵硫酸月桂基酯;烷芳基磺酸盐,比如十二烷基苯磺酸钙;烷基酚/氧化烯加成产物,比如壬基酚乙氧基化物;醇/烯烃氧化物加成产物,比如十三烷醇乙氧基化物;皂,比如硬脂酸钠;烷基萘磺酸盐,比如二丁基萘磺酸钠;磺基琥珀酸盐的二烷基酯,比如二(2-乙基己基)磺基琥珀酸钠;山梨糖醇酯,比如山梨糖醇油酸酯;季胺类,比如十二烷基三甲基氯化铵;脂肪酸的聚乙二醇酯,比如聚乙二醇硬脂酸酯;环氧乙烷和环氧丙烷的嵌段共聚物;以及单-烷基与二烷基磷酸酯的盐;以及还有其他物质,例如描述于:McCutcheon's Detergents and Emulsifiers Annual[麦卡琴清洁剂和乳化剂年鉴],MC出版公司(MC Publishing Corp.),里奇伍德,新泽西州(Ridgewood New Jersey)(1981)。
可以用于杀有害生物配制品的其他佐剂包括结晶作用抑制剂、粘度改性剂、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,所述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。在根据本发明所述的组合物中的油添加剂的量通常是所述待施用的混合物的0.01%到10%。例如,可以在喷雾混合物已经制备以后将所述油添加剂以所希望的浓度加入喷雾罐中。优选的油添加剂包括矿物油或植物来源的油,例如菜籽油、橄榄油或葵花籽油;乳化的植物油;植物来源的油的烷基酯,例如甲基衍生物;或动物来源的油,如鱼油或牛脂。优选的油添加剂包括C8-C22脂肪酸的烷基酯,尤其是C12-C18脂肪酸的甲基衍生物,例如月桂酸、棕榈酸以及油酸(分别为月桂酸甲酯、棕榈酸甲酯和油酸甲酯)的甲基酯。许多油衍生物获知于以下文献:Compendium of HerbicideAdjuvants,10th Edition,Southern Illinois University,2010[除草剂佐剂纲要,第10版,南伊利诺伊大学,2010]。
这些本发明组合物总体上包括按重量计从0.1%至99%,尤其是按重量计从0.1%至95%的本发明的化合物以及按重量计从1%至99.9%的配制佐剂,所述配制佐剂优选地包括按重量计从0至25%的表面活性物质。而商用产品可以优选地被配制为浓缩物,最终使用者将通常使用稀释配制品。
施用比率在宽范围之内变化并且取决于土壤的性质、施用方法、作物植物、待控制的有害生物、主要气候条件、以及受施用方法、施用时间以及目标作物支配的其他因素。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%):
可乳化的浓缩物:
活性成分:1%至95%,优选60%至90%
表面活性剂:1%至30%,优选5%至20%
液体载体:1%至80%,优选1%至35%
尘剂:
活性成分:0.1%至10%,优选0.1%至5%
固体载体:99.9%至90%,优选99.9%至99%
悬浮液浓缩物:
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的环氧乙烷) | - | 2% | - |
高度分散的硅酸 | 5% | 10% | 10% |
高岭土 | 62% | 27% | - |
将所述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。
<u>干种子处理用的粉剂</u> | a) | b) | c) |
活性成分 | 25% | 50% | 75% |
轻质矿物油 | 5% | 5% | 5% |
高度分散的硅酸 | 5% | 5% | - |
高岭土 | 65% | 40% | - |
滑石 | - | - | 20% |
将所述组合与佐剂充分混合并且将所述混合物在适合的研磨机中充分研磨,从而获得可以直接用于种子处理的粉剂。
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% |
通过将所述组合与载体混合并且将混合物在适当的研磨机中研磨获得立即可用的尘剂。此类粉剂还可以用于种子的干拌种。
<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% |
将所述组合与这些佐剂混合并且研磨,并且将混合物用水湿润。
将混合物挤出并且然后在空气流中干燥。
<u>包衣的颗粒剂</u> | |
活性成分 | 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于用聚乙二醇湿润的高岭土中。以此方式获得无尘的包衣的颗粒剂。
<u>悬浮液浓缩物</u> | |
活性成分 | 40% |
丙二醇 | 10% |
壬基苯酚聚乙二醇醚(15mol的环氧乙烷) | 6% |
木质素磺酸钠 | 10% |
羧甲基纤维素 | 1% |
硅油(处于在水中75%的乳液的形式) | 1% |
水 | 32% |
将精细研磨的组合与佐剂密切混合,从而给出悬浮液浓缩物,可以通过使用水稀释从所述浓缩物获得任何所希望稀释度的悬浮液。使用这样的稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷洒、倾倒或浸渍进行保护。
<u>种子处理用的可流动性浓缩物</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% |
将精细研磨的组合与佐剂密切混合,从而给出悬浮液浓缩物,可以通过使用水稀释从所述浓缩物获得任何所希望稀释度的悬浮液。使用这样的稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷洒、倾倒或浸渍进行保护。
缓释的胶囊悬浮液
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粒度。向此乳液中加入在5.3份的水中的2.8份的1,6-己二胺混合物。将混合物搅拌直至聚合反应完成。将获得的胶囊悬浮液通过加入0.25份的增稠剂以及3份的分散剂进行稳定。所述胶囊悬浮液配制品包含28%的活性成分。所述介质胶囊的直径是8微米-15微米。将所得配制品作为适用于此目的装置中的水性悬浮液施用到种子上。
配制品类型包括乳液浓缩剂(EC)、悬浮液浓缩物(SC)、悬乳剂(SE)、胶囊悬浮液(CS)、水可分散性颗粒剂(WG)、可乳化的颗粒剂(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)、可溶性浓缩物(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。
在另一方面,本发明使得一种杀有害生物组合物可供使用,所述组合物包含第一方面的化合物、一种或多种配制添加剂、和载体。
通过添加其他杀昆虫、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,并且适合于普遍情况。具有式(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进一步地、令人惊讶的优点,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,添加的适当活性成分的代表是以下类别的活性成分: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、新烟碱以及苏芸金芽孢杆菌制剂。
具有式(I)的化合物与活性成分的以下混合物是优选的(缩写“TX”意指“选自下组的一种化合物,所述组由以下组成:表1(下文)中列出的化合物1.001至1.105或表A(下文)中列出的化合物A1至A102”):
佐剂,所述佐剂选自由以下各项组成的物质组:石油(628)+TX,
杀螨剂,所述杀螨剂选自由以下各项组成的物质组:1,1-双(4-氯苯基)-2-乙氧基乙醇(IUPAC名称)(910)+TX、2,4-二氯苯基苯磺酸盐(IUPAC/化学文摘名称)(1059)+TX、2-氟-N-甲基-N-1-萘基乙酰胺(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、赛果(870)+TX、磺胺螨酯[CCN]+TX、果满磷(872)+TX、胺吸磷(875)+TX、胺吸磷草酸氢盐(875)+TX、双甲脒(24)+TX、杀螨特(881)+TX、三氧化二砷(882)+TX、AVI 382(化合物代码)+TX、AZ 60541(化合物代码)+TX、乙基谷硫磷(44)+TX、甲基谷硫磷(45)+TX、偶氮苯(IUPAC名称)(888)+TX、三唑锡(46)+TX、偶氮磷(889)+TX、苯菌灵(62)+TX、苯噁磷(别名)[CCN]+TX、苯螨特(71)+TX、苯甲酸苄酯(IUPAC名称)[CCN]+TX、联苯肼酯(74)+TX、联苯菊酯(76)+TX、乐杀螨(907)+TX、溴灭菊酯(别名)+TX、溴烯杀(918)+TX、溴硫磷(920)+TX、乙基溴硫磷(921)+TX、溴螨酯(94)+TX、稻虱净(99)+TX、丁酮威(103)+TX、丁酮砜威(104)+TX、丁基哒螨灵(别名)+TX、多硫化钙(IUPAC名称)(111)+TX、毒杀芬(941)+TX、氯灭杀威(943)+TX、西维因(115)+TX、卡巴呋喃(118)+TX、三硫磷(947)+TX、CGA50’439(开发代码)(125)+TX、灭螨猛(126)+TX、氯杀螨(959)+TX、杀虫脒(964)+TX、杀虫脒盐酸盐(964)+TX、溴虫腈(130)+TX、杀螨醇(968)+TX、杀螨酯(970)+TX、敌螨丹(971)+TX、毒虫畏(131)+TX、克氯苯(975)+TX、灭螨眯(977)+TX、灭虫脲(978)+TX、丙酯杀螨醇(983)+TX、毒死蜱(145)+TX、甲基毒死蜱(146)+TX、虫螨磷(994)+TX、瓜菊酯I(696)+TX、瓜菊酯II(696)+TX、瓜菊酯(696)+TX、四螨嗪(158)+TX、氯氰碘柳胺(别名)[CCN]+TX、蝇毒磷(174)+TX、克罗米通(别名)[CCN]+TX、丁烯磷(1010)+TX、硫杂灵(1013)+TX、果虫磷(1020)+TX、丁氟螨酯(CAS登记号:400882-07-7)+TX、三氟氯氰菊酯(196)+TX、三环锡(199)+TX、氯氰菊酯(201)+TX、DCPM(1032)+TX、DDT(219)+TX、田乐磷(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、二嗪农(227)+TX、抑菌灵(230)+TX、敌敌畏(236)+TX、二克磷(dicliphos)(别名)+TX、开乐散(242)+TX、百治磷(243)+TX、除螨灵(1071)+TX、甲氟磷(1081)+TX、乐果(262)+TX、二活菌素(别名)(653)+TX、消螨酚(1089)+TX、消螨酚(dinex-diclexine)(1089)+TX、消螨通(269)+TX、敌螨普(270)+TX、敌螨普-4[CCN]+TX、敌螨普-6[CCN]+TX、邻敌螨消(1090)+TX、硝戊酯(1092)+TX、硝辛酯(1097)+TX、硝丁酯(1098)+TX、敌杀磷(1102)+TX、二苯砜(IUPAC名称)(1103)+TX、戒酒硫(别名)[CCN]+TX、乙拌磷(278)+TX、DNOC(282)+TX、苯氧炔螨(1113)+TX、多拉菌素(别名)[CCN]+TX、硫丹(294)+TX、因毒磷(1121)+TX、EPN(297)+TX、依立诺克丁(别名)[CCN]+TX、乙硫磷(309)+TX、益果(1134)+TX、乙螨唑(320)+TX、乙嘧硫磷(1142)+TX、抗螨唑(1147)+TX、喹螨醚(328)+TX、苯丁锡(330)+TX、苯硫威(337)+TX、甲氰菊酯(342)+TX、吡螨胺(别名)+TX、唑螨酯(345)+TX、除螨酯(1157)+TX、芳氟胺(1161)+TX、氰戊菊酯(349)+TX、氟虫腈(354)+TX、嘧螨酯(360)+TX、啶蜱脲(1166)+TX、氟螨噻(1167)+TX、氟环脲(366)+TX、氟氰戊菊酯(367)+TX、联氟螨(1169)+TX、氟虫脲(370)+TX、氟氯苯菊酯(372)+TX、氟杀螨(1174)+TX、氟胺氰菊酯(1184)+TX、FMC 1137(开发代码)(1185)+TX、杀螨脒(405)+TX、杀螨脒盐酸盐(405)+TX、安果(1192)+TX、胺甲威(1193)+TX、γ-HCH(430)+TX、果绿定(1205)+TX、苄螨醚(424)+TX、庚烯磷(432)+TX、十六烷基环丙烷甲酸酯(IUPAC/化学文摘名称)(1216)+TX、噻螨酮(441)+TX、碘甲烷(IUPAC名称)(542)+TX、水胺硫磷(别名)(473)+TX、异丙基O-(甲氧基氨基硫代磷酰基)水杨酸盐(IUPAC名称)(473)+TX、伊佛霉素(别名)[CCN]+TX、茉莉菊酯I(696)+TX、茉莉菊酯II(696)+TX、碘硫磷(1248)+TX、灵丹(430)+TX、氯芬奴隆(490)+TX、马拉硫磷(492)+TX、丙螨氰(1254)+TX、灭蚜磷(502)+TX、地胺磷(1261)+TX、甲硫芬(别名)[CCN]+TX、虫螨畏(1266)+TX、甲胺磷(527)+TX、杀扑磷(529)+TX、灭虫威(530)+TX、灭多虫(531)+TX、甲基溴(537)+TX、速灭威(550)+TX、速灭磷(556)+TX、兹克威(1290)+TX、密灭汀(557)+TX、米尔贝肟(别名)[CCN]+TX、丙胺氟(1293)+TX、久效磷(561)+TX、茂果(1300)+TX、莫昔克丁(别名)[CCN]+TX、二溴磷(567)+TX、NC-184(化合物代码)+TX、NC-512(化合物代码)+TX、氟蚁灵(1309)+TX、日光霉素(nikkomycins)(别名)[CCN]+TX、戊氰威(1313)+TX、戊氰威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、氧化乐果(594)+TX、草氨酰(602)+TX、异亚砜磷(1324)+TX、砜拌磷(1325)+TX、pp'-DDT(219)+TX、对硫磷(615)+TX、苄氯菊酯(626)+TX、石油(别名)(628)+TX、芬硫磷(1330)+TX、稻丰散(631)+TX、甲拌磷(636)+TX、伏杀磷(637)+TX、硫环磷(1338)+TX、亚胺硫磷(638)+TX、磷胺(639)+TX、辛硫磷(642)+TX、甲基嘧啶磷(652)+TX、聚氯萜烯(传统名称)(1347)+TX、浏阳霉素(653)+TX、丙氯醇(1350)+TX、丙溴磷(662)+TX、蜱虱威(1354)+TX、克螨特(671)+TX、巴胺磷(673)+TX、残杀威(678)+TX、乙噻唑磷(1360)+TX、发硫磷(1362)+TX、除虫菊酯I(696)+TX、除虫菊酯II(696)+TX、除虫菊酯(696)+TX、哒螨灵(699)+TX、哒嗪硫磷(701)+TX、嘧螨醚(706)+TX、嘧硫磷(1370)+TX、喹硫磷(quinalphos)(711)+TX、喹硫磷(quintiofos)(1381)+TX、R-1492(开发代码)(1382)+TX、RA-17(开发代码)(1383)+TX、鱼藤酮(722)+TX、八甲磷(1389)+TX、克线丹(别名)+TX、司拉克丁(别名)[CCN]+TX、SI-0009(化合物代码)+TX、苏硫磷(1402)+TX、螺螨酯(738)+TX、螺甲螨酯(739)+TX、SSI-121(开发代码)(1404)+TX、舒非仑(别名)[CCN]+TX、氟虫胺(750)+TX、治螟磷(753)+TX、硫磺(754)+TX、SZI-121(开发代码)(757)+TX、τ-氟胺氰菊酯(398)+TX、吡螨胺(763)+TX、TEPP(1417)+TX、叔丁威(别名)+TX、杀虫畏(777)+TX、四氯杀螨砜(786)+TX、杀螨素(别名)(653)+TX、杀螨好(1425)+TX、噻芬诺(别名)+TX、抗虫威(1431)+TX、久效威(800)+TX、甲基乙拌磷(801)+TX、克杀螨(1436)+TX、苏云金素(别名)[CCN]+TX、威菌磷(1441)+TX、苯螨噻(1443)+TX、三唑磷(820)+TX、唑蚜威(triazuron)(别名)+TX、敌百虫(824)+TX、三氯丙氧磷(1455)+TX、三活菌素(别名)(653)+TX、蚜灭多(847)+TX、氟吡唑虫(vaniliprole)[CCN]和YI-5302(化合物代码)+TX,
杀藻剂,所述杀藻剂选自由以下各项组成的物质组: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(quinocl胺)(714)+TX、醌萍胺(quinonamid)(1379)+TX、西玛津(730)+TX、三苯锡乙酸盐(IUPAC名称)(347)和氢氧化三苯锡(IUPAC名称)(347)+TX,
驱蠕虫剂,所述驱蠕虫剂选自由以下各项组成的物质组:阿巴美丁(1)+TX、克芦磷酯(1011)+TX、多拉克汀[CCN]+TX、依马克丁(291)+TX、依马克丁苯甲酸酯(291)+TX、依立诺克丁[CCN]+TX、伊维菌素[CCN]+TX、米尔倍霉素[CCN]+TX、莫昔克丁[CCN]+TX、哌嗪[CCN]+TX、塞拉菌素(selamectin)[CCN]+TX、多杀菌素(737)和硫菌灵(thiophanate)(1435)+TX,
杀鸟剂,所述杀鸟剂选自由以下各项组成的物质组:氯醛糖(127)+TX、异狄氏剂(1122)+TX、倍硫磷(346)+TX、吡啶-4-胺(IUPAC名称)(23)和士的宁(745)+TX,
杀细菌剂,所述杀细菌剂选自由以下各项组成的物质组: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[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[CCN]+TX,
生物试剂,所述生物试剂选自由以下各项组成的物质组:棉褐带卷蛾颗粒体病毒(Adoxophyes orana GV)(12)+TX、放射形土壤杆菌(13)+TX、捕食螨(Amblyseius spp.)(19)+TX、芹菜夜蛾核多角体病毒(Anagrapha falcifera NPV)(28)+TX、Anagrus atomus(29)+TX、短距蚜小蜂(Aphelinus abdominalis)(33)+TX、棉蚜寄生蜂(Aphidiuscolemani)(34)+TX、食蚜瘿蚊(Aphidoletes aphidimyza)(35)+TX、苜蓿银纹夜蛾核多角体病毒(Autographa californica NPV)(38)+TX、坚硬芽孢杆菌(Bacillus firmus)(48)+TX、球形芽孢杆菌(Bacillus sphaericus Neide)(学名)(49)+TX、苏云金芽孢杆菌(Bacillusthuringiensis Berliner)(学名)(51)+TX、苏云金芽孢杆菌鲇泽亚种(Bacillusthuringiensis subsp.aizawai)(学名)(51)+TX、苏云金芽孢杆菌以色列亚种(Bacillusthuringiensis subsp.israelensis)(学名)(51)+TX、苏云金芽孢杆菌日本亚种(Bacillusthuringiensis subsp.japonensis)(学名)(51)+TX、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensis 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、球孢白僵菌(Beauveria bassiana)(53)+TX、布氏白僵菌(Beauveria brongniartii)(54)+TX、草蜻蛉(Chrysoperla carnea)(151)+TX、孟氏隐唇瓢虫(Cryptolaemus montrouzieri)(178)+TX、苹果蠹蛾颗粒体病毒(Cydia pomonella GV)(191)+TX、西伯利亚离颚茧蜂(Dacnusasibirica)(212)+TX、豌豆潜叶蝇姬小蜂(Diglyphus isaea)(254)+TX、丽蚜小蜂(Encarsiaformosa)(学名)(293)+TX、桨角蚜小蜂(Eretmocerus eremicus)(300)+TX、玉米穗夜蛾核多角体病毒(Helicoverpa zea NPV)(431)+TX、嗜菌异小杆线虫(Heterorhabditisbacteriophora)和H.megidis(433)+TX、会聚长足瓢虫(Hippodamia convergens)(442)+TX、橘粉介壳虫寄生蜂(Leptomastix dactylopii)(488)+TX、盲蝽(Macrolophuscaliginosus)(491)+TX、甘蓝夜蛾核多角体病毒(Mamestra brassicae NPV)(494)+TX、Metaphycus helvolus(522)+TX、黄绿绿僵菌(Metarhizium anisopliae var.acridum)(学名)(523)+TX、金龟子绿僵菌小孢变种(Metarhizium anisopliae var.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(575)+TX、小花蝽(596)+TX、玫烟色拟青霉(Paecilomyces fumosoroseus)(613)+TX、智利捕植螨(Phytoseiulus persimilis)(644)+TX、甜菜夜蛾(Spodopteraexigua multicapsid)多核衣壳核多角体病毒(学名)(741)+TX、毛蚊线虫(Steinernemabibionis)(742)+TX、小卷蛾斯氏线虫(Steinernema carpocapsae)(742)+TX、夜蛾斯氏线虫(742)+TX、Steinernema glaseri(742)+TX、Steinernema riobrave(另名)(742)+TX、Steinernema riobravis(742)+TX、Steinernema scapterisci(742)+TX、斯氏线虫属(Steinernema spp.)(742)+TX、赤眼蜂属(826)+TX、西方盲走螨(Typhlodromusoccidentalis)(844)和蜡蚧轮枝菌(Verticillium lecanii)(848)+TX,
土壤消毒剂,所述土壤消毒剂选自由以下各项组成的物质组:碘甲烷(IUPAC名称)(542)和甲基溴(537)+TX,
化学不育剂,所述化学不育剂选自由以下各项组成的物质组:唑磷嗪(apholate)[CCN]+TX、双(氮丙啶)甲氨基膦硫化物(二azir)[CCN]+TX、白消安[CCN]+TX、除虫脲(250)+TX、迪麦替夫(dimatif)[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(甲基apholate)[CCN]+TX、不孕啶(morzid)[CCN]+TX、氟幼脲(penfluron)[CCN]+TX、涕巴(tepa)[CCN]+TX、硫代六甲磷(thiohempa)[CCN]+TX、硫涕巴[CCN]+TX、曲他胺[CCN]和尿烷亚胺[CCN]+TX,
昆虫信息素,所述昆虫信息素选自由以下各项组成的物质组:(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)[CCN]+TX、西部松小蠹集合信息素(brevicomin)[CCN]+TX、十二碳二烯醇(codlelure)[CCN]+TX、十二碳二烯醇(codlemone)(167)+TX、诱蝇酮(cuelure)(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[CCN]+TX、4-甲基辛酸乙酯(IUPAC名称)(317)+TX、丁香酚[CCN]+TX、南部松小蠹集合信息素(frontalin)[CCN]+TX、诱虫十六酯(gossyplure)(420)+TX、诱杀烯混剂(grandlure)(421)+TX、诱杀烯混剂I(421)+TX、诱杀烯混剂II(421)+TX、诱杀烯混剂III(421)+TX、诱杀烯混剂IV(421)+TX、醋酸十六烯酯(hexalure)[CCN]+TX、齿小蠹二烯醇(ipsdienol)[CCN]+TX、小蠢烯醇(ipsenol)[CCN]+TX、金龟子性诱剂(japonilure)(481)+TX、lineatin[CCN]+TX、litlure[CCN]+TX、粉纹夜蛾性诱剂(looplure)[CCN]+TX、诱杀酯(medlure)[CCN]+TX、megatomoic acid[CCN]+TX、诱虫醚(methyl eugenol)(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)[CCN]+TX、oryctalure(317)+TX、非乐康(ostramone)[CCN]+TX、诱虫环(siglure)[CCN]+TX、sordidin(736)+TX、食菌甲诱醇(sulcatol)[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(839)+TX、特诱酮B1(839)+TX、特诱酮B2(839)+TX、特诱酮C(839)和trunc-call[CCN]+TX,
昆虫驱避剂,所述昆虫驱避剂选自由以下各项组成的物质组: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,
杀昆虫剂,所述杀昆虫剂选自由以下各项组成的物质组:1-二氯-1-硝基乙烷(IUPAC/化学文摘名称)(1058)+TX、1,1-二氯-2,2-双(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、1,2-二氯丙烷与1,3-二氯丙烯(IUPAC名称)(1063)+TX、1-溴-2-氯乙烷(IUPAC/化学文摘名称)(916)+TX、2,2,2-三氯-1-(3,4-二氯苯基)乙基乙酸酯(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盐(IUPAC名称)(1066)+TX、2-(1,3-二四氢噻吩-2-基)苯基二甲基氨基甲酸酯(IUPAC/化学文摘名称)(1109)+TX、2-(2-丁氧基乙氧基)乙基硫氰酸酯(IUPAC/化学文摘名称)(935)+TX、2-(4,5-二甲基-1,3-二氧戊环-2-基)苯基甲基氨基甲酸酯(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-咪唑烷酮(IUPAC名称)(1225)+TX、2-异戊酰茚满-1,3-二酮(IUPAC名称)(1246)+TX、2-甲基(丙-2-炔基)氨基苯基甲基氨基甲酸酯(IUPAC名称)(1284)+TX、2-硫代氰酰乙基十二酸酯(IUPAC名称)(1433)+TX、3-溴-1-氯丙-1-烯(IUPAC名称)(917)+TX、3-甲基-1-苯基吡唑-5-基二甲基氨基甲酸酯(IUPAC名称)(1283)+TX、4-甲基(丙-2-炔基)氨基-3,5-二甲苯基甲基氨基甲酸酯(IUPAC名称)(1285)+TX、5,5-二甲基-3-氧代环己-1-烯基二甲基氨基甲酸酯(IUPAC名称)(1085)+TX、阿维菌素(1)+TX、高灭磷(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、艾氏剂(864)+TX、丙烯菊酯(17)+TX、阿洛氨菌素(别名)[CCN]+TX、除害威杀虫剂(866)+TX、α-氯氰菊酯(202)+TX、α-蜕化素(别名)[CCN]+TX、磷化铝(640)+TX、赛果(870)+TX、果满磷(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、甲基吡噁磷(42)+TX、乙基谷硫磷(44)+TX、甲基谷硫磷(45)+TX、偶氮磷(889)+TX、苏云金芽孢杆菌δ内毒素(别名)(52)+TX、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、拜耳22/190(开发代码)(893)+TX、拜耳22408(开发代码)(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、生物丙烯菊酯(78)+TX、生物丙烯菊酯S-环戊烯基同分异构体(别名)(79)+TX、生物乙菊酯(bioethanomethrin)[CCN]+TX、生物氯菊酯(biopermethrin)(908)+TX、菊精(80)+TX、双(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、溴烯杀(918)+TX、溴-DDT(别名)[CCN]+TX、溴硫磷(920)+TX、乙基溴硫磷(921)+TX、合杀威(924)+TX、稻虱净(99)+TX、畜虫威(926)+TX、特嘧硫磷(butathiofos)(927)+TX、丁酮威(103)+TX、丁酯磷(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、胺甲萘(115)+TX、卡巴呋喃(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、丁硫克百威(119)+TX、杀螟丹(123)+TX、杀螟丹盐酸盐(123)+TX、瑟瓦定(别名)(725)+TX、冰片丹(960)+TX、氯丹(128)+TX、十氯酮(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、氯腈肟磷(989)+TX、灭虫吡啶(chlorprazophos)(990)+TX、毒死蜱(145)+TX、甲基毒死蜱(146)+TX、虫螨磷(994)+TX、环虫酰肼(150)+TX、瓜菊酯I(696)+TX、瓜菊酯II(696)+TX、瓜菊酯(696)+TX、灭虫菊(cis-resmethrin)+TX、顺式苄呋菊酯(别名)(80)+TX、氰菊酯(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、丁烯磷(1010)+TX、育畜磷(1011)+TX、冰晶石(cryolite)(别名)(177)+TX、CS 708(开发代码)(1012)+TX、苯腈膦(1019)+TX、杀螟腈(184)+TX、果虫磷(1020)+TX、环虫菊[CCN]+TX、乙氰菊酯(188)+TX、氟氯氰菊酯(193)+TX、三氟氯氰菊酯(196)+TX、氯氰菊酯(201)+TX、苯醚氰菊酯(206)+TX、灭蝇胺(209)+TX、赛灭磷(别名)[CCN]+TX、右旋柠檬烯(别名)[CCN]+TX、右旋胺菊酯(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、甲基内吸磷(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、杀线虫剂(diamidafos)(1044)+TX、二嗪农(227)+TX、异氯磷(1050)+TX、除线磷(1051)+TX、敌敌畏(236)+TX、二克磷(dicliphos)(别名)+TX、二甲苯基(dicresyl)(别名)[CCN]+TX、百治磷(243)+TX、地昔尼尔(244)+TX、狄氏剂(1070)+TX、二乙基5-甲基吡唑-3-基磷酸盐(IUPAC名称)(1076)+TX、二氟脲(250)+TX、二羟丙茶碱(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、苄菌酯(1083)+TX、二甲基毒虫威(265)+TX、敌蝇威(1086)+TX、消螨酚(1089)+TX、消螨酚(dinex-diclexine)(1089)+TX、硝丙酚(1093)+TX、戊硝酚(1094)+TX、地乐酚(1095)+TX、呋虫胺(271)+TX、苯虫醚(1099)+TX、蔬果磷(1100)+TX、二氧威(1101)+TX、敌杀磷(1102)+TX、乙拌磷(278)+TX、地可磷(1108)+TX、DNOC(282)+TX、多拉菌素(别名)[CCN]+TX、DSP(1115)+TX、脱皮甾酮(别名)[CCN]+TX、EI 1642(开发代码)(1118)+TX、埃玛菌素(291)+TX、埃玛菌素苯甲酸盐(291)+TX、EMPC(1120)+TX、烯炔菊酯(292)+TX、硫丹(294)+TX、因毒磷(1121)+TX、异狄氏剂(1122)+TX、EPBP(1123)+TX、EPN(297)+TX、保幼醚(epofenonane)(1124)+TX、依立诺克丁(别名)[CCN]+TX、高氰戊菊酯(302)+TX、牛津郡丙硫磷(etaphos)(别名)[CCN]+TX、乙硫苯威(308)+TX、乙硫磷(309)+TX、乙虫腈(310)+TX、益果(1134)+TX、灭线磷(312)+TX、甲酸乙酯(IUPAC名称)[CCN]+TX、乙基-DDD(别名)(1056)+TX、二溴化乙烯(316)+TX、二氯乙烷(化学名称)(1136)+TX、环氧乙烷[CCN]+TX、依芬普司(319)+TX、乙嘧硫磷(1142)+TX、EXD(1143)+TX、氨磺磷(323)+TX、克线磷(326)+TX、抗螨唑(1147)+TX、皮蝇硫磷(1148)+TX、双乙威(1149)+TX、芬氟司林(1150)+TX、杀螟硫磷(335)+TX、仲丁威(336)+TX、氧嘧酰胺(fenoxacrim)(1153)+TX、苯氧威(340)+TX、吡氯氰菊酯(1155)+TX、甲氰菊酯(342)+TX、吡螨胺(fenpyrad)(别名)+TX、丰索磷(1158)+TX、倍硫磷(346)+TX、倍硫磷-乙基[CCN]+TX、氰戊菊酯(349)+TX、氟虫腈(354)+TX、氟啶虫酰胺(358)+TX、氟虫双酰胺(CAS登记号:272451-65-7)+TX、氟氯双苯隆(flucofuron)(1168)+TX、氟环脲(366)+TX、氟氰戊菊酯(367)+TX、联氟螨(1169)+TX、嘧虫胺[CCN]+TX、氟虫脲(370)+TX、三氟醚菊酯(1171)+TX、氟氯苯菊酯(372)+TX、氟胺氰菊酯(1184)+TX、FMC 1137(研究代码)(1185)+TX、地虫磷(1191)+TX、伐虫脒(405)+TX、伐虫脒盐酸盐(405)+TX、安硫磷(1192)+TX、藻螨威(formparanate)(1193)+TX、丁苯硫磷(1194)+TX、福司吡酯(1195)+TX、噻唑酮磷(408)+TX、丁硫环磷(1196)+TX、呋线威(412)+TX、抗虫菊(1200)+TX、γ-氯氟氰菊酯(197)+TX、γ-HCH(430)+TX、双胍盐(422)+TX、双胍醋酸盐(422)+TX、GY-81(研究代码)(423)+TX、苄螨醚(424)+TX、氯虫酰肼(425)+TX、HCH(430)+TX、HEOD(1070)+TX、飞布达(1211)+TX、庚烯磷(432)+TX、速杀硫磷[CCN]+TX、氟铃脲(439)+TX、HHDN(864)+TX、氟蚁腙(443)+TX、氢氰酸(444)+TX、烯虫乙酯(445)+TX、海驱威(hyquincarb)(1223)+TX、吡虫啉(458)+TX、炔咪菊酯(460)+TX、茚虫威(465)+TX、碘甲烷(IUPAC名称)(542)+TX、IPSP(1229)+TX、氯唑磷(1231)+TX、碳氯灵(1232)+TX、水胺硫磷(473)+TX、异艾氏剂(1235)+TX、异柳磷(1236)+TX、移栽灵(1237)+TX、异丙威(472)+TX、O-(甲氧基氨基硫代磷酰基)水杨酸异丙酯(IUPAC名称)(473)+TX、稻瘟灵(474)+TX、异拌磷(1244)+TX、恶唑磷(480)+TX、伊维菌素[CCN]+TX、茉酮菊素I(696)+TX、茉酮菊素II(696)+TX、碘硫磷(1248)+TX、保幼激素I[CCN]+TX、保幼激素II[CCN]+TX、保幼激素III[CCN]+TX、氯戊环(1249)+TX、烯虫炔酯(484)+TX、λ-氯氟氰菊酯(198)+TX、砷酸铅[CCN]+TX、雷皮菌素(CCN)+TX、对溴磷(1250)+TX、林旦(430)+TX、丙嘧硫磷(lirimfos)(1251)+TX、虱螨脲(490)+TX、噻唑磷(1253)+TX、间异丙基苯基甲基氨基甲酸酯(IUPAC名称)(1014)+TX、磷化镁(IUPAC名称)(640)+TX、马拉硫磷(492)+TX、特螨腈(1254)+TX、叠氮磷(1255)+TX、灭蚜磷(502)+TX、四甲磷(1258)+TX、灭蚜硫磷(1260)+TX、地安磷(1261)+TX、氯化亚汞(513)+TX、甲亚砜磷(1263)+TX、氰氟虫腙(CCN)+TX、威百亩(519)+TX、威百亩-钾盐(519)+TX、威百亩-钠盐(519)+TX、虫螨畏(1266)+TX、甲胺磷(527)+TX、甲基磺酰氟(IUPAC/化学文摘名)(1268)+TX、杀扑磷(529)+TX、甲硫威(530)+TX,丁烯胺磷(1273)+TX、灭多威(531)+TX、烯虫酯(532)+TX、甲喹丁(1276)+TX、甲醚菊酯(533)+TX、甲氧滴滴涕(534)+TX、甲氧虫酰肼(535)+TX、溴甲烷(537)+TX、异硫氰酸甲酯(543)+TX、甲基氯仿[CCN]+TX、二氯甲烷[CCN]+TX、甲氧苄氟菊酯[CCN]+TX、速灭威(550)+TX、恶虫酮(1288)+TX、速灭磷(556)+TX、自克威(1290)+TX、弥拜菌素(557)+TX、杀螨菌素肟[CCN]+TX、丙胺氟磷(1293)+TX、灭蚁灵(1294)+TX、久效磷(561)+TX、茂硫磷(1300)+TX,莫西菌素[CCN]+TX、奈肽磷[CCN]+TX、二溴磷(567)+TX、萘(IUPAC/化学文摘名)(1303)+TX,NC-170(研究代码)(1306)+TX、NC-184(化合物代码)+TX、烟碱(578)+TX、烟碱硫酸盐(578)+TX、氟蚊灵(1309)+TX、烯啶虫胺(579)+TX、硝虫噻嗪(1311)+TX、戊氰威(1313)+TX、戊氰威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、原烟碱(传统名称)(1319)+TX、氟酰脲(585)+TX、多氟脲(586)+TX、O-5-二氯-4-碘代苯基O-乙基乙基硫代磷酸酯(IUPAC名称)(1057)+TX、O,O--二乙基O-4-甲基-2-氧代-2H-苯并吡喃-7-基硫代磷酸酯(IUPAC名称)(1074)+TX、O,O-二乙基O-6-甲基-2-丙基嘧啶-4-基硫代磷酸酯(IUPAC名称)(1075)+TX、O,O,O',O’-四丙基二硫代焦磷酸酯(IUPAC名称)(1424)+TX、油酸(IUPAC名称)(593)+TX、氧乐果(594)+TX、杀线威(602)+TX、砜吸碑(609)+TX、亚异砜辨(1324)+TX、砜拌碑(1325)+TX、pp,-DDT(219)+TX,对二氯苯[CCN]+TX、对硫磷(615)+TX、甲基对硫磷(616)+TX、氟幼脲[CCN]+TX、五氯酚(623)+TX、月桂酸五氯苯酯(IUPAC名称)(623)+TX、氯菊酯(626)+TX、石油(628)+TX、PH 60-38(研究代码)(1328)+TX、芬硫磷(1330)+TX、苯醚菊酯(630)+TX、稻丰散(631)+TX、甲拌磷(636)+TX、伏杀硫磷(637)+TX,硫环磷(1338)+TX、亚胺硫磷(638)+TX、对氯硫磷(1339)+TX、磷胺(639)+TX、磷化氢(IUPAC名称)(640)+TX、辛硫磷(642)+TX,甲基辛硫磷(1340)+TX、甲胺嘧磷(1344)+TX、抗蚜威(651)+TX,乙基嘧啶磷(1345)+TX、嘧啶磷-甲基(652)+TX、多氯二环戊二烯同分异构体(IUPAC名称)(1346)+TX、亚砷酸氢钾[CCN]+TX、硫氰酸钾[CCN]+TX、炔丙菊酯(655)+TX、早熟素I[CCN]+TX、早熟素II[CCN]+TX、早熟素III[CCN]+TX、皮瑞米多夫(primidophos)(1349)+TX、丙溴磷(662)+TX、普若夫拉林(profluthrin)[CCN]+TX、蜱虱威(1354)+TX、猛杀威(1355)+TX、丙虫磷(1356)+TX、胺丙畏(673)+TX、残杀威(678)+TX、乙噻唑磷(1360)+TX、丙硫磷(686)+TX、发硫磷(1362)+TX、扑瑞赛分布特(protrifenbute)[CCN]+TX、吡蚜酮(688)+TX、吡唑硫磷(689)+TX、定菌磷(693)+TX、吡热梅林(pyresmethrin)(1367)+TX、除虫菊酯I(696)+TX、除虫菊酯II(696)+TX、除虫菊酯(696)+TX、哒螨灵(699)+TX、啶虫丙醚(700)+TX、哒嗪硫磷(701)+TX、嘧螨醚(706)+TX、嘧硫磷(1370)+TX、吡丙醚(708)+TX、苦木[CCN]+TX、喹硫磷(711)+TX、喹硫磷-甲基(1376)+TX、奎诺塞(quinothion)(1380)+TX、喹硫磷(1381)+TX、R-1492(研究代码)(1382)+TX、碘醚硫胺[CCN]+TX、苄氟菊酯(719)+TX、鱼藤酮(722)+TX、RU 15525(研究代码)(723)+TX、RU 25475(研究代码)(1386)+TX、鱼尼定(1387)+TX、利阿诺丁(传统名称)(1387)+TX、沙巴藜芦(725)+TX、八甲磷(1389)+TX、克线单+TX、斯拉克顶[CCN]+TX、SI-0009(化合物代码)+TX、SI-0205(化合物代码)+TX、SI-0404(化合物代码)+TX、SI-0405(化合物代码)+TX、氟硅菊酯(728)+TX、SN 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)(1399)+TX、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、萨科伏龙(sulcofuron)(746)+TX、萨科伏龙(sulcofuron)-钠(746)+TX、氟虫胺(750)+TX、治螟灵(753)+TX、磺酰氟(756)+TX、硫丙磷(1408)+TX、焦油(758)+TX、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、甲烯菊酯(1418)+TX、叔丁威+TX、特丁磷(773)+TX、四氯乙烷[CCN]+TX、杀虫威(777)+TX、胺菊酯(787)+TX、高效反式氯氰菊酯(204)+TX、噻虫啉(791)+TX、噻吩诺(thiafenox)+TX、噻虫嗪(792)+TX、塞克若夫(thicrofos)(1428)+TX、抗虫威(1431)+TX、杀虫环(798)+TX、杀虫环杀虫环(798)+TX、硫双威(799)+TX、久效威(800)+TX、甲基乙拌磷(801)+TX、硫磷嗪(1434)+TX、杀虫单(803)+TX、杀虫双(803)+TX、苏云金素[CCN]+TX、唑虫酰胺(809)+TX、四溴菊酯(812)+TX、四氟苯菊酯(813)+TX、反式二氯苯醚菊酯(1440)+TX、威菌磷(1441)+TX、唑蚜威(818)+TX、三唑磷(820)+TX、塞族融(triazuron)+TX、敌百虫(824)+TX、塞克罗梅塔氟(trichlormetaphos)-3[CCN]+TX、虫壤膦(1452)+TX、司服诺夫斯(trifenofos)(1455)+TX、杀铃脲(835)+TX、混杀灭(840)+TX、烯虫硫酯(1459)+TX、蚜灭多(847)+TX、瓦尼利普诺(vaniliprole)[CCN]+TX、藜芦定(725)+TX、藜芦碱(725)+TX、XMC(853)+TX、灭杀威(854)+TX、YI-5302(化合物代码)+TX、六氯氰菊酯(205)+TX、扎他莫森(zetamethrin)+TX、磷化锌(640)+TX、左拉铺诺夫斯(zolaprofos)(1469)和ZXI 8901(研究代码)(858)+TX、氰虫酰胺[736994-63-19+TX、氯虫苯甲酰胺[500008-45-7]+TX、腈吡螨酯[560121-52-0]+TX、丁氟螨酯[400882-07-7]+TX、新喹唑啉[337458-27-2]+TX、乙基多杀菌素[187166-40-1+187166-15-0]+TX、螺虫乙酯[203313-25-1]+TX、砜虫啶[946578-00-3]+TX、丁烯氟虫腈[704886-18-0]+TX、氯氟醚菊酯[915288-13-0]+TX、四氟醚菊酯[84937-88-2]+TX、赛富美作派瑞(triflumezopyrim)(披露于WO 2012/092115)+TX,
杀软体动物剂,所述杀软体动物剂选自由以下各项组成的物质组:二(三丁基锡)氧化物(IUPAC名称)(913)+TX、溴乙酰胺[CCN]+TX、砷酸钙[CCN]+TX、除线威(cloethocarb)(999)+TX、乙酰亚砷酸铜[CCN]+TX、硫酸铜(172)+TX、三苯锡(347)+TX、磷酸铁(IUPAC名称)(352)+TX、四聚乙醛(518)+TX、灭虫威(530)+TX、氯硝柳胺(576)+TX、氯硝柳胺乙醇胺盐(576)+TX、五氯酚(623)+TX、五氯苯氧化钠(623)+TX、噻螨威(tazimcarb)(1412)+TX、硫双威(799)+TX、三丁基氧化锡(913)+TX、杀螺吗啉(trifenmorph)(1454)+TX、混杀威(trimethacarb)(840)+TX、乙酸三苯基锡(IUPAC名称)(347)和三苯基氢氧化锡(IUPAC名称)(347)+TX、皮瑞普(pyriprole)[394730-71-3]+TX,
杀线虫剂,所述杀线虫剂选自由以下各项组成的物质组: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(210)+TX、阿巴美丁(1)+TX、乙酰虫腈[CCN]+TX、棉铃威(15)+TX、涕灭威(aldicarb)(16)+TX、涕灭砜威(aldoxycarb)(863)+TX、AZ 60541(化合物代码)+TX、benclothiaz[CCN]+TX、苯菌灵(62)+TX、丁基哒螨酮(butylpyridaben)+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)(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)+TX、乐果(262)+TX、依马克丁[CCN]+TX、苯甲酸依马克丁(291)+TX、依立诺克丁(291)+TX、[CCN]+TX、灭线磷(312)+TX、二溴乙烷(316)+TX、苯线磷(fenamiphos)(326)+TX、吡螨胺+TX、丰索磷(fenpyrad)(1158)+TX、噻唑磷(fosthiazate)(408)+TX、丁硫环磷(fosthietan)(1196)+TX、糠醛[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)[CCN]+TX、糠氨基嘌呤(mecarphon)(210)+TX、甲基灭蚜磷(mecarphon)(1258)+TX、威百亩(519)+TX、威百亩钾盐(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)[CCN]+TX、莫昔克丁(剔名)[CCN]+TX、疣孢漆斑菌(Myrothecium verrucaria)组分(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)+TX、塞拉菌素(selamectin)[CCN]+TX、多杀菌素(737)+TX、叔丁威(terbam)+TX、特丁磷(terbufos)(773)+TX、四氯噻吩(IUPAC/化学文摘名)(1422)+TX、thiafenox+TX、虫线磷(thionazin)(1434)+TX、三唑磷(triazophos)(820)+TX、triazuron+TX、二甲苯酚[CCN]+TX、YI-5302(化合物代码)和玉米素(210)+TX、fluensulfone[318290-98-1]+TX,
硝化作用抑制剂,所述硝化作用抑制剂选自由以下各项组成的物质组:乙基黄原酸钾[CCN]以及氯啶(nitrapyrin)(580)+TX,
植物激活剂,所述植物激活剂选自由以下各项组成的物质组: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(720)+TX,
杀鼠剂,所述杀鼠剂选自由以下各项组成的物质组: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(850)+TX、氯灭鼠灵(1004)+TX、克灭鼠(1005)+TX、杀鼠萘(175)+TX、杀鼠嘧啶(1009)+TX、鼠得克(246)+TX、噻鼠灵(249)+TX、敌鼠钠(273)+TX、维生素D2(301)+TX、氟鼠灵(357)+TX、氟乙酰胺(379)+TX、鼠朴定(1183)+TX、盐酸鼠朴定(1183)+TX、γ-HCH(430)+TX、HCH(430)+TX、氢氰酸(444)+TX、碘甲烷(IUPAC名称)(542)+TX、林旦(430)+TX、磷化镁(IUPAC名称)(640)+TX、甲基溴(537)+TX、鼠特灵(1318)+TX、毒鼠磷(1336)+TX、磷化氢(IUPAC名称)(640)+TX、磷[CCN]+TX、杀鼠酮(1341)+TX、亚砷酸钾[CCN]+TX、灭鼠优(1371)+TX、海葱糖苷(1390)+TX、亚砷酸钠[CCN]+TX、氰化钠(444)+TX、氟乙酸钠(735)+TX、士的宁(745)+TX、硫酸铊[CCN]+TX、杀鼠灵(851)以及磷化锌(640)+TX,
增效剂,所述增效剂选自由以下各项组成的物质组: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(324)+TX、MB-599(研究代码)(498)+TX、MGK264(研究代码)(296)+TX、增效醚(piperonyl butoxide)(649)+TX、增效醛(piprotal)(1343)+TX、增效酯(propyl isomer)(1358)+TX、S421(研究代码)(724)+TX、增效散(sesamex)(1393)+TX、芝麻林素(sesasmolin)(1394)和亚砜(1406)+TX,
动物驱避剂,所述动物驱避剂选自由以下各项组成的物质组: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、双胍乙酸盐(422)+TX、灭虫威(530)+TX、吡啶-4-胺(IUPAC名称)(23)+TX、塞仑(804)+TX、混杀威(trimethacarb)(840)+TX、环烷酸锌[CCN]和福美锌(856)+TX,
杀病毒剂,所述杀病毒剂选自由以下各项组成的物质组:衣马宁[CCN]和利巴韦林[CCN]+TX,
创伤保护剂,所述创伤保护剂选自由以下各项组成的物质组:氧化汞(512)+TX、辛噻酮(590)和甲基硫菌灵(802)+TX,
以及生物活性化合物,这些化合物选自由以下各项组成的组:阿扎康唑[60207-31-0]+TX、联苯三唑醇[70585-36-3]+TX、糠菌唑[116255-48-2]+TX、环唑醇[94361-06-5]+TX、苯醚甲环唑[119446-68-3]+TX、烯唑醇[83657-24-3]+TX、氟环唑[106325-08-0]+TX、腈苯唑[114369-43-6]+TX、氟喹唑[136426-54-5]+TX、氟硅唑[85509-19-9]+TX、粉唑醇[76674-21-0]+TX、己唑醇[79983-71-4]+TX、抑霉唑[35554-44-0]+TX、亚胺唑[86598-92-7]+TX、种菌唑[125225-28-7]+TX、叶菌唑[125116-23-6]+TX、腈菌唑[88671-89-0]+TX、稻瘟酯[101903-30-4]+TX、戊菌唑[66246-88-6]+TX、丙硫菌唑[178928-70-6]+TX、啶斑肟(pyrifenox)[88283-41-4]+TX、丙氯灵[67747-09-5]+TX、丙环唑[60207-90-1]+TX、硅氟唑(simeconazole)[149508-90-7]+TX、戊唑醇[107534-96-3]+TX、氟醚唑[112281-77-3]+TX、三唑酮[43121-43-3]+TX、三唑酮[55219-65-3]+TX、氟菌唑[99387-89-0]+TX、灭菌唑[131983-72-7]+TX、三环苯嘧醇[12771-68-5]+TX、氯苯嘧啶醇[60168-88-9]+TX、氟氯苯嘧啶醇[63284-71-9]+TX、乙嘧酚磺酸酯(bupirimate)[41483-43-6]+TX、甲菌定(dimethirimol)[5221-53-4]+TX、乙菌定(ethirimol)[23947-60-6]+TX、十二环吗啉[1593-77-7]+TX、苯锈啶(fenpropidine)[67306-00-7]+TX、丁苯吗啉[67564-91-4]+TX、螺环菌胺[118134-30-8]+TX、十三吗啉[81412-43-3]+TX、嘧菌环胺[121552-61-2]+TX、嘧菌胺[110235-47-7]+TX、嘧霉胺(pyrimethanil)[53112-28-0]+TX、拌种咯[74738-17-3]+TX、咯菌腈(fludioxonil)[131341-86-1]+TX、苯霜灵(benalaxyl)[71626-11-4]+TX、呋霜灵(furalaxyl)[57646-30-7]+TX、甲霜灵[57837-19-1]+TX、R-甲霜灵[70630-17-0]+TX、呋酰胺[58810-48-3]+TX、恶霜灵(Oxadixyl)[77732-09-3]+TX、苯菌灵[17804-35-2]+TX、多菌灵[10605-21-7]+TX、咪菌威(debacarb)[62732-91-6]+TX、麦穗宁[3878-19-1]+TX、噻苯达唑[148-79-8]+TX、乙菌利(chlozolinate)[84332-86-5]+TX、菌核利(dichlozoline)[24201-58-9]+TX、异菌脲(Iprodione)[36734-19-7]+TX、myclozoline[54864-61-8]+TX、腐霉利(procymidone)[32809-16-8]+TX、乙烯菌核利(vinclozoline)[50471-44-8]+TX、啶酰菌胺(boscalid)[188425-85-6]+TX、萎锈灵[5234-68-4]+TX、甲呋酰苯胺[24691-80-3]+TX、氟酰胺(Flutolanil)[66332-96-5]+TX、灭锈胺[55814-41-0]+TX、氧化萎锈灵[5259-88-1]+TX、吡噻菌胺(penthiopyrad)[183675-82-3]+TX、噻呋菌胺[130000-40-7]+TX、双胍盐[108173-90-6]+TX、多果定(dodine)[2439-10-3][112-65-2](游离键)+TX、双胍辛胺(iminoctadine)[13516-27-3]+TX、嘧菌酯[131860-33-8]+TX、醚菌胺[149961-52-4]+TX、烯肟菌酯{Proc.BCPC,Int.Congr.,Glasgow.2003,1,93}+TX、氟嘧菌酯[361377-29-9]+TX、甲基醚菌酯[143390-89-0]+TX、苯氧菌胺[133408-50-1]+TX、肟菌酯[141517-21-7]+TX、肟醚菌胺[248593-16-0]+TX、啶氧菌酯[117428-22-5]+TX、唑菌胺酯[175013-18-0]+TX、福美铁[14484-64-1]+TX、代森锰锌[8018-01-7]+TX、代森锰[12427-38-2]+TX、代森联[9006-42-2]+TX、甲代森锌(propineb)[12071-83-9]+TX、塞仑[137-26-8]+TX、代森锌[12122-67-7]+TX、福美锌[137-30-4]+TX、敌菌丹(captafol)[2425-06-1]+TX、克菌丹[133-06-2]+TX、苯氟磺胺[1085-98-9]+TX、唑啶草(fluoroimide)[41205-21-4]+TX、灭菌丹[133-07-3]+TX、甲苯氟磺胺[731-27-1]+TX、波尔多(bordeaux)混合物[8011-63-0]+TX、氢氧化铜(copperhydroxid)[20427-59-2]+TX、氯化铜(copperoxychlorid)[1332-40-7]+TX、硫酸铜(coppersulfat)[7758-98-7]+TX、氧化铜(copperoxid)[1317-39-1]+TX、代森锰铜(mancopper)[53988-93-5]+TX、喹啉铜(oxine-copper)[10380-28-6]+TX、敌螨普(dinocap)[131-72-6]+TX、酞菌酯(nitrothal-isopropyl)[10552-74-6]+TX、克瘟散[17109-49-8]+TX、异稻瘟净(iprobenphos)[26087-47-8]+TX、稻瘟灵(isoprothiolane)[50512-35-1]+TX、氯瘟磷(phosdiphen)[36519-00-3]+TX、克菌磷(pyrazophos)[13457-18-6]+TX、甲基托氯磷(tolclofos-methyl)[57018-04-9]+TX、苯并噻二唑(acibenzolar-S-methyl)[135158-54-2]+TX、敌菌灵[101-05-3]+TX、苯噻菌胺[413615-35-7]+TX、灭瘟素(blasticidin)-S[2079-00-7]+TX、灭螨猛(chinomethionat)[2439-01-2]+TX、地茂散(chloroneb)[2675-77-6]+TX、百菌清[1897-45-6]+TX、环氟菌胺[180409-60-3]+TX、霜脲氰[57966-95-7]+TX、二氯萘醌(dichlone)[117-80-6]+TX、双氯氰菌胺(diclocymet)[139920-32-4]+TX、哒菌酮(diclomezine)[62865-36-5]+TX、氯硝胺(dicloran)[99-30-9]+TX、乙霉威(diethofencarb)[87130-20-9]+TX、烯酰吗啉[110488-70-5]+TX、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-甲酸(9-二氯亚甲基-1,2,3,4-四氢-1,4-桥亚甲基-萘-5-基)-酰胺(披露于WO 2007/048556中)+TX、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(3’,4’,5’-三氟-联苯基-2-基)-酰胺(披露于WO2006/087343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、兰蔻三酮(lancotrione)[1486617-21-3]+TX、氯氟吡啶酯[943832-81-3]+TX、艾分氟康唑(ipfentrifluconazole)[1417782-08-1]+TX、氯氟醚菌唑(mefentrifluconazole)[1417782-03-6]+TX、quinofumelin[861647-84-9]+TX、右旋反式氯丙炔菊酯(chloroprallethrin)[399572-87-3]+TX、氯氟氰虫酰胺(cyhalodiamide)[1262605-53-7]+TX、三氟咪啶酰胺(fluazaindolizine)[1254304-22-7]+TX、fluxametamide[928783-29-3]+TX、ε-甲氧苄氟菊酯[240494-71-7]+TX、ε-氟氯氰菊酯(epsilon-momfluorothrin)[1065124-65-3]+TX、氟唑菌酰羟胺[1228284-64-7]+TX、κ-毕芬宁(kappa-bifenthrin)[439680-76-9]+TX、溴虫氟苯双酰胺(broflanilide)[1207727-04-5]+TX、敌克美施(dicloromezotiaz)[1263629-39-5]+TX、敌派美创(dipymetitrone)[16114-35-5]+TX、吡唑嘧啶(pyraziflumid)[942515-63-1]+TX、κ-七氟菊酯(kappa-tefluthrin)[391634-71-2]+TX、制定杀(fenpicoxamid)[517875-34-2]+TX、氟茚唑菌胺(fluindapyr)[1383809-87-7]+TX、α-溴敌隆(alpha-bromadiolone)[28772-56-7]+TX、flupyrimin[1689566-03-7]+TX、benzpyrimoxan[1449021-97-9]+TX、acynonapyr[1332838-17-1]+TX、inpyrfluxam[1352994-67-2]+TX、isoflucypram[1255734-28-1]+TX、tyclopyrazoflor[64309-03-1]+TX、spiropidion[1531626-08-0]+TX、tyclopyrazoflor[1477919-27-9]+TX、Dichloromezotiaz+TX、Momfluorothrin+TX、Fluopyram+TX、Tioxazafen+TX、Terpenoid blend+TX、Fluhexafon+TX、Cyclaniliprole+TX、以及spiropidion[1229023-00-0]+TX;以及
微生物,包括:鲁氏不动杆菌+TX、支顶孢属突起菌+TX+TX、支顶孢属头孢+TX+TX、支顶孢属柿(Acremonium diospyri)+TX、支顶孢属倒棍棒状的+TX、苹卷蛾颗粒体病毒属(AdoxGV)+TX、放射形土壤杆菌菌株K84+TX、交链格孢菌+TX、链格孢决明子+TX、链格孢属性(Alternaria destruens)+TX、白粉寄生孢+TX、黄曲霉AF36+TX、黄曲霉NRRL 21882+TX、曲霉属+TX、出芽短梗霉菌+TX、固氮螺菌属+TX、(+TX、TAZO)+TX、固氮菌属+TX、固氮菌属chroocuccum+TX、固氮菌属囊肿(BionaturalBlooming)+TX、解淀粉芽孢杆菌+TX、蜡样芽胞杆菌+TX、芽孢杆菌属菌株(Bacillus chitinosporus strain)CM-1+TX、芽孢杆菌属菌株(Bacillus chitinosporusstrain 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、B环状芽孢杆菌+TX、坚硬芽孢杆菌(+TX、+TX、)+TX、坚硬芽孢杆菌菌株I-1582+TX、巨大芽孢杆菌+TX、巨大芽孢杆菌+TX、巨大芽孢杆菌+TX、蕈状芽孢杆菌菌株AQ726+TX、乳头状瘤芽孢杆菌(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(Bacillus spahericus)+TX、芽孢杆菌+TX、芽孢杆菌菌株AQ175+TX、芽孢杆菌菌株AQ177+TX、芽孢杆菌菌株AQ178+TX、枯草芽孢杆菌属菌株QST 713(+TX、+TX、)+TX、枯草芽孢杆菌属菌株QST 714+TX、枯草芽孢杆菌属菌株AQ153+TX、枯草芽孢杆菌属菌株AQ743+TX、枯草芽孢杆菌属菌株QST3002+TX、枯草芽孢杆菌属菌株QST3004+TX、枯草芽孢杆菌属变种解淀粉芽孢杆菌菌株FZB24(+TX、)+TX、苏云金芽孢杆菌Cry 2Ae+TX、苏云金芽孢杆菌Cry1Ab+TX、苏云金芽孢杆菌鲇泽亚种(Bacillus thuringiensis aizawai)GC 91+TX、苏云金芽孢杆菌以色列亚种(Bacillus thuringiensis israelensis)(+TX、+TX、)+TX、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensiskurstaki)(+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+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(Bacillus thuringiensisvar.aizawai)(+TX、)+TX、细菌属(bacteria spp.)(+TX、+TX、)+TX、密执安棍状杆菌(Clavipacter michiganensis)的噬菌体+TX、+TX、球孢白僵菌(Beauveria bassiana)(+TX、Brocaril)+TX、球孢白僵菌GHA(Mycotrol+TX、Mycotrol+TX、)+TX、布氏白僵菌(Beauveriabrongniartii)(+TX、Schweizer+TX、)+TX、白僵菌属(Beauveria spp.)+TX、灰葡萄孢霉(Botrytis cineria)+TX、大豆慢生型根瘤菌(Bradyrhizobium japonicum)+TX、短短小芽孢杆菌(Brevibacillus brevis)+TX、苏云金芽孢杆菌拟步行甲亚种(Bacillus thuringiensistenebrionis)+TX、BtBooster+TX、洋葱伯克霍尔德菌(Burkholderiacepacia)(+TX、+TX、Blue)+TX、伯克霍尔德菌(Burkholderia gladii)+TX、唐菖蒲伯克霍尔德菌(Burkholderia gladioli)+TX、伯克霍尔德菌属(Burkholderia spp.)+TX、加拿大蓟真菌(Canadian thistle fungus)(CBHCanadian)+TX、奶酪假丝酵母(Candida butyri)+TX、无名假丝酵母(Candida famata)+TX、Candida fructus+TX、光滑念珠菌(Candida glabrata)+TX、吉利蒙念珠菌(Candida guilliermondii)+TX、口津假丝酵母(Candida melibiosica)+TX、橄榄假丝酵母(Candida oleophila)菌株O+TX、近平滑假丝酵母(Candida parapsilosis)+TX、菌膜假丝酵母(Candida pelliculosa)+TX、铁红假丝酵母(Candida pulcherrima)+TX、拉考夫假丝酵母(Candida reukaufii)+TX、齐藤假丝酵母(Candida saitoana)(+TX、)+TX、清酒假丝酵母(Candida sake)+TX、假丝酵母属(Candida spp.)+TX、纤细假丝酵母(Candida tenius)+TX、戴氏西地西菌(Cedecea dravisae)+TX、产黄纤维单胞菌(Cellulomonas flavigena)+TX、螺卷毛壳(Chaetomium cochliodes)+TX、球毛壳菌(Chaetomium globosum)+TX、铁杉紫色杆菌(Chromobacterium subtsugae)菌株PRAA4-1T+TX、枝状枝孢菌(Cladosporium cladosporioides)+TX、尖孢枝孢(Cladosporium oxysporum)+TX、Cladosporium chlorocephalum+TX、枝孢属(Cladosporium spp.)+TX、极细枝孢霉(Cladosporium tenuissimum)+TX、粉红粘帚霉(Clonostachys rosea)+TX、尖孢炭疽菌(Colletotrichum acutatum)+TX、盾壳霉(Coniothyrium minitans)(Cotans)+TX、盾壳霉属(Coniothyrium spp.)+TX、浅白隐球酵母(Cryptococcusalbidus)+TX、土生隐球菌(Cryptococcus humicola)+TX、Cryptococcus infirmo-miniatus+TX、罗伦隐球酵母(Cryptococcus laurentii)+TX、苹果异形小卷蛾颗粒体病毒(Cryptophlebia leucotreta granulovirus)+TX、坎平贪铜菌(Cupriavidus campinensis)+TX、苹果蠹蛾颗粒体病毒(Cydia pomonellagranulovirus)+TX、苹果蠹蛾颗粒体病毒(+TX、Madex+TX、Madex Max/)+TX、Cylindrobasidium laeve+TX、枝双孢霉属(Cylindrocladium)+TX、汉逊德巴利酵母(Debaryomyces hansenii)+TX、Drechslerahawaiinensis+TX、阴沟肠杆菌(Enterobacter cloacae)+TX、肠杆菌科(Enterobacteriaceae)+TX、毒力虫霉(Entomophtora virulenta)+TX、黑附球菌(Epicoccum nigrum)+TX、黑附球菌(Epicoccum purpurascens)+TX、附球孢菌+TX、菌属(Filobasidium floriforme)+TX、尖圭镰刀菌+TX、厚孢镰刀菌+TX、尖孢镰刀菌(/Biofox)+TX、层出镰孢+TX、镰刀菌+TX、白地霉(Galactomycesgeotrichum)+TX、胶枝霉属(Gliocladium catenulatum)(+TX、)+TX、红粘帚霉+TX、胶枝霉属+TX、绿粘帚霉+TX、颗粒体病毒+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(Lecanicillium muscarium)+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(Metschnikowia pulcherrima)+TX、Microdochiumdimerum+TX、蓝色小单孢菌(Micromonospora coerulea)+TX、Microsphaeropsis ochracea+TX、Muscodor albus 620+TX、Muscodorroseus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、Ophiostomapiliferum菌株D97+TX、粉质拟青霉(Paecilomyces farinosus)+TX、玫烟色拟青霉(+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)+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+TX、绿黄假单胞菌+TX、荧光假单胞菌+TX、Pseudozyma flocculosa菌株PF-A22 UL(Sporodex)+TX、纵沟柄锈菌(Puccinia canaliculata)+TX、Pucciniathlaspeos(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(Rhanellaaquatilis)+TX、拉恩菌属(Rhanella spp.)+TX、根瘤菌(Rhizobia)(+TX、)+TX、丝核菌属(Rhizoctonia)+TX、球状红球菌(Rhodococcus globerulus)菌株AQ719+TX、双倒卵形红冬孢酵母菌(Rhodosporidium diobovatum)+TX、圆红冬孢酵母菌(Rhodosporidium toruloides)+TX、红酵母属(Rhodotorula spp.)+TX、粘红酵母(Rhodotorula glutinis)+TX、禾本红酵母(Rhodotorula graminis)+TX、胶红酵母(Rhodotorula mucilagnosa)+TX、深红酵母(Rhodotorula rubra)+TX、酿酒酵母(Saccharomyces cerevisiae)+TX、玫瑰色盐水球菌(Salinococcus roseus)+TX、小核盘菌(Sclerotinia minor)+TX、小核盘菌+TX、柱顶孢霉属(Scytalidiumspp.)+TX、Scytalidium uredinicola+TX、甜菜夜蛾核型多角体病毒(Spodoptera exiguanuclear polyhedrosis virus)(+TX、)+TX、粘质沙雷氏菌(Serratiamarcescens)+TX、普城沙雷菌(Serratia plymuthica)+TX、沙雷氏菌属(Serratia spp.)+TX、粪生粪壳菌(Sordaria fimicola)+TX、海灰翅夜蛾核型多角体病毒(Spodopteralittoralis nucleopolyhedrovirus)+TX、红掷孢酵母(Sporobolomycesroseus)+TX、嗜麦芽寡养单胞菌(Stenotrophomonas maltophilia)+TX、不吸水链霉菌(Streptomyces ahygroscopicus)+TX、白丘链霉菌(Streptomyces albaduncus)+TX、脱叶链霉菌(Streptomyces exfoliates)+TX、鲜黄链霉菌(Streptomyces galbus)+TX、灰平链霉菌(Streptomyces griseoplanus)+TX、灰绿链霉菌(Streptomyces griseoviridis)+TX、利迪链霉菌(Streptomyces lydicus)+TX、利迪链霉菌WYEC-108+TX、紫色链霉菌(Streptomyces violaceus)+TX、小铁艾酵母(Tilletiopsis minor)+TX、铁艾酵母属(Tilletiopsis spp.)+TX、棘孢木霉(Trichoderma asperellum)(T34)+TX、盖姆斯木霉(Trichoderma gamsii)+TX、深绿木霉(Trichoderma atroviride)+TX、钩状木霉(Trichodermahamatum)TH 382+TX、里法哈茨木霉(Trichoderma harzianum rifai)+TX、哈茨木霉(Trichoderma harzianum)T-22(+TX、PlantShield+TX、+TX、)+TX、哈茨木霉(Trichoderma harzianum)T-39+TX、非钩木霉(Trichoderma inhamatum)+TX、康宁木霉(Trichodermakoningii)+TX、木霉属(Trichoderma spp.)LC 52+TX、木素木霉(Trichoderma lignorum)+TX、长柄木霉(Trichoderma longibrachiatum)+TX、多孢木霉(Trichoderma polysporum)(Binab)+TX、紫杉木霉(Trichoderma taxi)+TX、绿色木霉(Trichoderma virens)+TX、绿色木霉(原来称为绿色粘帚霉(Gliocladium virens)GL-21)+TX、绿色木霉(Trichoderma viride)+TX、绿色木霉菌株ICC 080+TX、茁芽丝孢酵母(Trichosporon pullulans)+TX、毛孢子菌属(Trichosporon spp.)+TX、单端孢属(Trichothecium spp.)+TX、粉红单端孢(Trichothecium roseum)+TX、Typhula phacorrhiza菌株94670+TX、Typhula phacorrhiza菌株94671+TX、黑细基格孢(Ulocladium atrum)+TX、奥德曼细基格孢(Ulocladiumoudemansii)+TX、玉蜀黍黑粉菌(Ustilago maydis)+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(Verticillium chlamydosporium)+TX、蜡蚧轮枝菌(Verticillium lecanii)(+TX、)+TX、Vip3Aa20+TX、Virgibaclillusmarismortui+TX、野油菜黄单胞菌(Xanthomonas campestris pv.Poae)+TX、伯氏致病杆菌+TX、嗜线虫致病杆菌;以及
植物提取物,包括:松油+TX、印楝素(Plasma Neem+TX、+TX、+TX、+TX、植物IGR+TX、菜籽油(Lilly Miller)+TX、土荆芥附近荆芥(Chenopodium ambrosioides near ambrosioides)+TX、菊花浓汁(Chrysanthemum extract)+TX、提取印楝油(extract of neem oil)+TX、唇形科的精油+TX、丁香迷迭香薄荷的提取物和百里香精油(Garden insect)+TX、甜菜碱+TX、大蒜+TX、柠檬草精油+TX、印度楝树精油+TX、猫薄荷(薄荷精油)+TX、荆芥卡塔琳娜州(Nepeta catarina)+TX、尼古丁+TX、牛至精油+TX、胡麻科精油+TX、除虫菊+TX、皂皮树+TX、大虎杖(Reynoutriasachalinensis)(+TX、)+TX、鱼藤酮(Eco)+TX、芸香料植物提取物+TX、豆油(Ortho)+TX、茶树精油(Timorex)+TX、百里香精油+TX、MMF+TX、+TX、迷迭香芝麻薄荷百里香和肉桂提取物的混合物(EF)+TX、丁香迷迭香和薄荷提取物的混合物(EF)+TX、丁香薄荷大蒜油和薄菏的混合物(Soil)+TX、高岭土+TX、储存葡萄糖的褐藻+TX,以及
信息素,包括:黑头萤火虫信息素(3M喷洒型黑头萤火虫信息素)+TX、苹果蠹蛾信息素(派拉蒙分配器(Paramount dispenser)-(CM)/Isomate)+TX、葡萄卷叶蛾信息素(3M MEC-GBM喷洒型信息素)+TX、卷叶虫信息素(3M MEC–LR喷洒型信息素)+TX、家蝇信息素(Snip7Fly+TX、Starbar Premium Fly)+TX、梨小食心虫信息素(3M梨小食心虫喷洒型信息素)+TX、桃树钻心虫信息素+TX、番茄蛲虫信息素(3M喷洒型信息素)+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、+TX、薰衣草千里酸酯;以及
大生物(macrobial),包括:短距蚜小蜂(Aphelinus abdominalis)+TX、阿尔蚜茧蜂(Aphidius ervi)+TX、木瓜抑虱跳小蜂(Acerophaguspapaya)+TX、二星瓢虫(Adalia bipunctata)+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(Ageniaspis fuscicollis)+TX、安氏钝绥螨(Amblyseiusandersoni)(+TX、)+TX、加州钝绥螨(Amblyseiuscalifornicus)(+TX、))+TX、胡瓜钝绥螨(Amblyseiuscucumeris)(+TX、Bugline)+TX、伪钝绥螨(Amblyseiusfallacis)+TX、瑞氏钝绥螨(Amblyseius swirskii)(Bugline+TX、)+TX、奥氏钝绥螨(Amblyseius womersleyi)+TX、粉虱细蜂(Amitus hesperidum)+TX、原缕翅缕小蜂(Anagrusatomus)+TX、暗腹长索跳小蜂(Anagyrus fusciventris)+TX、卡玛长索跳小蜂(Anagyruskamali)+TX、Anagyrus loecki+TX、粉蚧长索跳小蜂(Anagyrus pseudococci)+TX、红蜡蚧扁角跳小蜂(Anicetus benefices)+TX、象虫金小蜂(Anisopteromalus calandrae)+TX、林地花蝽(Anthocoris nemoralis)+TX、短距蚜小蜂(+TX、)+TX、短翅蚜小蜂(Aphelinus asychis)+TX、科列马阿布拉小蜂(Aphidius colemani)+TX、阿尔蚜茧蜂(Aphidius ervi)+TX、烟蚜茧蜂(Aphidius gifuensis)+TX、桃赤蚜蚜茧蜂(Aphidius matricariae)+TX、食蚜癭蚊(Aphidoletes aphidimyza)+TX、食蚜癭蚊+TX、黄蚜小蜂(Aphytis lingnanensis)+TX、印巴黄蚜小蜂(Aphytismelinus)+TX、蜚卵啮小蜂(Aprostocetus hagenowii)+TX、隐翅虫(Atheta coriaria)+TX、熊蜂属(Bombus spp.)+TX、欧洲熊蜂(Bombus terrestris)(Natupol)+TX、欧洲熊蜂(+TX、)+TX、Cephalonomiastephanoderis+TX、Chilocorus nigritus+TX、普通草铃(Chrysoperla carnea)+TX、普通草铃+TX、Chrysoperla rufilabris+TX、Cirrospilus ingenuus+TX、蛹寄生蜂(Cirrospilus quadristriatus)+TX、白腹啮小蜂(Citrostichus phyllocnistoides)+TX、Closterocerus chamaeleon+TX、Closterocerusspp.+TX、Coccidoxenoides perminutus+TX、Coccophagus cowperi+TX、赖食蚧蚜小蜂(Coccophagus lycimnia)+TX、螟黄足盘绒茧蜂(Cotesia flavipes)+TX、菜蛾盘绒茧蜂(Cotesia plutellae)+TX、孟氏隐唇瓢虫(Cryptolaemus montrouzieri)(+TX、)+TX、日本方头甲(Cybocephalus nipponicus)+TX、西伯利亚离颚茧蜂(Dacnusa sibirica)+TX、西伯利亚离颚茧蜂+TX、豌豆潜蝇姬小蜂(Diglyphus isaea)+TX、小黑瓢虫(Delphastus catalinae)+TX、Delphastus pusillus+TX、Diachasmimorpha krausii+TX、长尾潜蝇茧蜂(Diachasmimorpha longicaudata)+TX、长凹姬蜂(Diaparsis jucunda)+TX、阿里食虱跳小蜂(Diaphorencyrtus aligarhensis)+TX、豌豆潜蝇姬小蜂(Diglyphus isaea)+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(Diversinervus spp.)+TX、盾蚧长缨蚜小蜂(Encarsia citrina)+TX、丽蚜小蜂(Encarsia formosa)(Encarsia+TX、+TX、)+TX、浆角蚜小蜂(Eretmocerus eremicus)+TX、哥德恩蚜小蜂(Encarsia guadeloupae)+TX、海地恩蚜小蜂(Encarsiahaitiensis)+TX、细扁食蚜蝇(Episyrphus balteatus)+TX、Eretmoceris siphonini+TX、加州桨角蚜小蜂(Eretmocerus californicus)+TX、浆角蚜小蜂(Eretmocerus eremicus)(+TX、Eretline)+TX、浆角蚜小蜂+TX、海氏桨角蚜小蜂(Eretmocerus hayati)+TX、蒙氏桨角蚜小蜂(Eretmocerus mundus)(+TX、Eretline)+TX、Eretmocerus siphonini+TX、四斑光缘瓢虫(Exochomus quadripustulatus)+TX、食螨癭蚊(Feltiella acarisuga)+TX、食螨癭蚊+TX、阿里山潜蝇茧蜂(Fopius arisanus)+TX、Fopius ceratitivorus+TX、芒柄花黄素(Formononetin)(Wirless)+TX、细腰凶蓟马(Franklinothrips vespiformis)+TX、西方静走螨(Galendromus occidentalis)+TX、莱氏棱角肿腿蜂(Goniozus legneri)+TX、麦蛾柔茧蜂(Habrobracon hebetor)+TX、异色瓢虫(Harmonia axyridis)+TX、异小杆线虫属(Heterorhabditis spp.)(Lawn)+TX、嗜菌异小杆线虫(Heterorhabditis bacteriophora)(NemaShield+TX、+TX、+TX、+TX、+TX、+TX、+TX、)+TX、大异小杆线虫(Heterorhabditis megidis)(Nemasys+TX、BioNem+TX、Exhibitline+TX、)+TX、集栖瓢虫(Hippodamia convergens)+TX、尖狭下盾螨(Hypoaspis aculeifer)(+TX、)+TX、兵下盾螨(Hypoaspis miles)(Hypoline+TX、)+TX、黑色枝跗瘿蜂(Lbalia leucospoides)+TX、Lecanoideus floccissimus+TX、Lemophagus errabundus+TX、三色刚突跳小蜂(Leptomastidea abnormis)+TX、Leptomastix dactylopii+TX、长角跳小蜂(Leptomastix epona)+TX、Lindorus lophanthae+TX、Lipolexis oregmae+TX、叉叶绿蝇(Lucilia caesar)+TX、茶足柄瘤蚜茧蜂(Lysiphlebus testaceipes)+TX、暗黑长脊盲蝽(Macrolophus caliginosus)(+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(Neoseiuluscalifornicus)+TX、黄瓜新小绥螨(Neoseiulus cucumeris)+TX、虚伪新小绥螨(Neoseiulus fallacis)+TX、Nesideocoris tenuis(+TX、)+TX、古铜黑蝇(Ophyra aenescens)+TX、狡诈花蝽(Oriusinsidiosus)(+TX、Oriline)+TX、无毛小花蝽(Orius laevigatus)(+TX、Oriline)+TX、大型小花蝽(Orius majusculus)(Oriline)+TX、小黑花椿象(Orius strigicollis)+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(Phytoseiulus persimilis)(+TX、Phytoline)+TX、斑腹刺益蝽(Podisus maculiventris)+TX、Pseudacteon curvatus+TX、Pseudacteonobtusus+TX、火蚁寄生蚤蝇(Pseudacteon tricuspis)+TX、Pseudaphycus maculipennis+TX、Pseudleptomastix mexicana+TX、具毛嗜木虱跳小蜂(Psyllaephagus pilosus)+TX、同色短背茧蜂(Psyttalia concolor)(complex)+TX、胯姬小蜂属(Quadrastichus spp.)+TX、Rhyzobius lophanthae+TX、澳洲瓢虫(Rodolia cardinalis)+TX、Rumina decollate+TX、Semielacher petiolatus+TX、麦长管蚜+TX、小卷蛾斯氏线虫(Steinernema carpocapsae)(Nematac+TX、+TX、BioNem+TX、+TX、+TX、)+TX、夜蛾斯氏线虫(Steinernema feltiae)(+TX、Nemasys+TX、BioNem+TX、+TX、+TX、+TX、Exhibitline+TX、+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(Steinernema spp.)+TX、Steinernematid spp.(Guardian)+TX、深点食螨瓢虫(Stethoruspunctillum)+TX、亮腹釉小蜂(Tamarixia radiate)+TX、Tetrastichussetifer+TX、Thripobius semiluteus+TX、中华长尾小蜂(Torymus sinensis)+TX、甘蓝夜蛾赤眼蜂(Trichogramma brassicae)(Tricholine)+TX、甘蓝夜蛾赤眼蜂+TX、广赤眼蜂(Trichogramma evanescens)+TX、微小赤眼蜂(Trichogramma minutum)+TX、玉米螟赤眼蜂(Trichogramma ostriniae)+TX、宽脉赤眼蜂(Trichogramma platneri)+TX、短管赤眼蜂(Trichogramma pretiosum)+TX、螟黑点瘤姬蜂(Xanthopimpla stemmator),以及
其他生物制剂,包括:脱落酸+TX、+TX、紫韧革菌(Chondrostereumpurpureum)(Chontrol)+TX、胶孢炭疽菌(Colletotrichum gloeosporioides)+TX、辛酸铜+TX、三角洲陷阱(Delta trap)(Trapline)+TX、梨火疫病菌(Erwinia amylovora)(Harpin)(+TX、Ni-HIBIT Gold)+TX、磷酸铁+TX、漏斗陷阱(Funnel trap)(Trapline)+TX、+TX、Grower's+TX、高油菜素内酯(Homo-brassonolide)+TX、磷酸铁(LillyMiller Worry Free Ferramol Slug&Snail)+TX、MCP冰雹陷阱(MCP hail trap)(Trapline)+TX、象甲和寄生蜂(Microctonus hyperodae)+TX、大豆红褐坏死病菌(Mycoleptodiscus terrestris)+TX、+TX、+TX、+TX、信息素陷阱(Pheromone trap)(Thripline)+TX、碳酸氢钾+TX、脂肪酸钾盐+TX、硅酸钾溶液+TX、碘化钾+硫氰酸钾+TX、+TX、蜘蛛毒液+TX、蝗虫小孢子虫(Nosema locustae)(Semaspore Organic Grasshopper)+TX、粘滞陷阱(Sticky trap)(Trapline+TX、Rebell)+TX和陷阱(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。上文描述的混合配伍物是已知的。当活性成分包括在“The Pesticide Manual[杀有害生物剂手册]”[The Pesticide Manual-A World Compendium[杀有害生物剂手册-全球概览];第十三版;编著:C.D.S.Tomlin(汤姆林);英国农作物保护委员会(The Pesticide Manual-AWorld Compendium;Thirteenth Edition;Editor:C.D.S.TomLin;The British CropProtection 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所述手册中;例如,化合物“阿巴美丁”在条目编号(1)之下描述。当上文对特定化合物添加“[CCN]”时,所考虑的化合物包括在“Compendium of Pesticide Common Names”[杀虫剂通用名纲要]中,所述纲要可在互联网上获得[A.Wood;Compendium of Pesticide Common Names[杀虫剂通用名纲要],Copyright1995-2004];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。
多数活性成分通过上文中所谓的“通用名”来表示,在不同的情形中使用相应的“ISO通用名”或另一“通用名”。如果名称不是“通用名”,那么所用名称的性质实际上指定在特定化合物的圆括号中;在那种情况下,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“开发代码”。“CAS登记号”意指化学文摘登记号。
选自表1(下文)中列出的化合物1.001至1.105或表A(下文)中列出的化合物A1至A102的具有式(I)的化合物的活性成分混合物与上述活性成分的比率(按重量计)是从100:1至1:6000、尤其从50:1至1:50,更尤其处于以下比率:从20:1至1:20、甚至更尤其从10:1至1:10、非常尤其从5:1和1:5,特别优选从2:1至1:2的比率,并且从4:1至2:1的比率同样是优选的,尤其是处于以下比率: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。
如上所述的混合物可以被用于控制有害生物的方法中,所述方法包括将含如上所述的混合物的组合物施用于有害生物或其环境中,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除外。
包含选自表1(下文)中列出的化合物1.001至1.105或表A(下文)中列出的化合物A1至A102的具有式(I)的化合物以及一种或多种如上所述的活性成分的混合物可以例如以单一的“掺水即用”的形式施用,以组合的喷雾混合物(所述混合物由这些单一活性成分组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,例如几小时或几天)施用时组合使用这些单独活性成分来施用。施用选自表1(下文)中列出的化合物1.001至1.105或表A(下文)中列出的化合物A1至A102的具有式(I)的化合物以及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。
在另一方面,本发明提供了活性成分的组合,其包含第一方面中定义的化合物、以及一种或多种另外的活性成分(无论是化学的还是生物的)。
根据本发明的组合物还可以包含其他固体或液体助剂,例如稳定剂,例如未环氧化的或环氧化的植物油(例如环氧化的椰子油、菜籽油或大豆油),消泡剂(例如硅酮油),防腐剂,粘度调节剂,粘合剂和/或增粘剂,肥料或其他用于获得特定效果的活性成分,例如杀细菌剂、杀真菌剂、杀线虫剂、植物活化剂、杀软体动物剂或除草剂。
根据本发明的组合物是以本身已知的方式,在不存在助剂的情况下,例如通过研磨、筛选和/或压缩固体活性成分;和在至少一种助剂的存在下,例如通过紧密混合活性成分与一种或多种助剂和/或将活性成分与一种或多种助剂一起研磨来制备。用于制备组合物的这些方法和用于制备这些组合物的化合物(I)的用途也是本发明的主题。
这些组合物的施用方法,即控制上述类型的有害生物的方法,如喷雾、雾化、撒粉、刷涂、包衣、撒播或浇灌-它们被选择以适于普遍情况的预期目的-以及这些组合物用于控制上述类型的有害生物的用途是本发明的其他主题。典型的浓度比是在0.1与1000ppm之间,优选在0.1与500ppm之间的活性成分。每公项的施用量总体上是每公项1g到2000g活性成分,尤其是10g/ha到1000g/ha,优选地是10g/ha到600g/ha。
在作物保护领域中,优选的施用方法是施用至这些植物的叶(叶施药),可能的是选择施用的频率和比率以符合所讨论的有害生物的侵染风险。可替代地,所述活性成分可以通过根系统(内吸作用)到达植物,这是通过用一种液体组合物将这些植物的所在地浸透或者通过将固体形式的活性成分引入植物的所在地(例如引入土壤,例如以颗粒(土施)的形式)来实现的。在水稻作物的情况下,这样的颗粒剂可以被计量地加入淹水的稻田中。
本发明的这些化合物及其组合物还适合于植物繁殖材料的保护(例如种子,像果实、块茎或籽粒,或者苗圃植物),以对抗上述类型的有害生物。可以用所述化合物在种植前对所述繁殖材料进行处理,例如可以在播种前对种子进行处理。可替代地,所述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包衣固体组合物层实现的。还可能在所述繁殖材料被种植在施用处时施用所述组合物,例如在条播期间将所述组合物施入种子犁沟。这些用于植物繁殖材料的处理方法和因此处理的植物繁殖材料是本发明另外的主题。典型的处理比率将取决于有待控制的植物以及有害生物/真菌,通常在每100kg种子1克至200克之间、优选在每100kg种子5克至150克之间、例如在每100kg种子10克至100克之间。
术语种子包括所有种类的种子以及植物繁殖体,包括但并不限于真正的种子、种子块、吸盘、谷粒、鳞球茎、果实、块茎、谷物、根茎、插条、切割枝条以及类似物并且在优选实施例中意指真正的种子。
本发明还包括经具有化学式(I)的化合物包衣或处理或含有具有化学式I的化合物的种子。尽管取决于施用的方法成分的更多或更少的部分可以渗透到所述种子材料中,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,所述活性成分在所述种子的表面。当所述种子产品被(再)种植时,它可以吸收活性成分。在实施例中,本发明使得其上粘附有具有式(I)的化合物的植物繁殖材料可得。此外,由此可得包含用具有式(I)的化合物处理过的植物繁殖材料的组合物。
种子处理包括本领域中已知的所有合适的种子处理技术,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。
另一方面是植物繁殖材料,其包含通过处理或涂覆一种或多种根据本发明的具有式(I)的合物,任选地还包含彩色颜料。
在本发明的每个方面以及实施例中,“基本上由……组成”以及其变形是“包含”以及其变形的优选实施例,并且“由……组成”以及其变形是“基本上由……组成”以及其变形的优选实施例。
本申请的披露使得在此披露的实施例的各自并且每一个组合可得。
表1:此表披露了105种具有式(I-1)的化合物:
其中,m是0,R3a和R3b是氢,并且R1和R4是如下表中所定义的。
实例
接下来的实例用来阐明本发明。
本发明的化合物与已知的化合物的区别可以在于在低施用率下更大的效力,这可以由本领域的技术人员使用在实例中概述的实验程序,使用更低的施用率(如果必要的话)例如,50ppm、12.5ppm、6ppm、3ppm、1.5ppm、0.8ppm或0.2ppm,或更低的施用率如300、200或100mg的AI/m2来证实。
具有式(I)的化合物可以具有任何数量的益处,尤其包括对于保护植物抵抗昆虫的有利水平的生物活性或对于用作农用化学品活性成分的优越特性(例如,更高的生物活性、有利的活性谱、增加的安全性(包括改善的作物耐受性)、改善的物理-化学特性、或增加的生物可降解性)。
贯穿本说明书,以摄氏度(℃)给出温度并且“mp”意指熔点。
LC/MS意指液相色谱法质谱法,并且所述装置和方法A的描述在下文中概述。对于每种化合物获得的特征LC/MS值是保留时间(“Rt”,以分钟(min)记录)和测量的分子离子(M+H)+和/或(M-H)-。
1H NMR测量值在Brucker 400MHz或300MHz分光计上记录,化学位移相对于TMS标准物以ppm给出。光谱在氘化溶剂(例如二甲亚砜(DMSO))中测量,如所示的。
方法A-标准
在来自沃特斯公司(Waters)的质谱仪(SQD,SQDII单四极杆质谱仪)上光谱记录,所述质谱仪配备有电喷射源(极性:正离子和负离子,毛细管:3.00kV,锥孔范围:30V,萃取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:50l/h,去溶剂化气体流量:650l/h;质量范围:100Da至900Da)以及来自沃特斯公司的Acquity UPLC:二元泵,经加热的柱室,二极管阵列检测器和ELSD检测器。柱:沃特斯公司的UPLC HSS T3,1.8μm,30x2.1mm,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B:
在来自沃特斯公司的ACQUITY质谱仪(SQD或SQDII单四极杆质谱仪)上记录光谱,所述质谱仪配备有电喷射源(极性:正离子或负离子,毛细管:3.0kV,锥孔:30V,萃取器:3.00V,源温度:150℃,去溶剂化温度:400℃,锥孔气体流量:60L/hr,去溶剂化气体流量:700L/hr,质量范围:140Da至800Da),以及来自沃特斯公司的ACQUITY UPLC(具有溶剂脱气装置、二元泵、经加热的柱室以及二极管阵列检测器)。柱:沃特斯公司的UPLC HSS T3,1.8μm,30x 2.1mm,温度:60℃,DAD波长范围(nm):210至400,溶剂梯度:A=水/甲醇9:1+0.1%甲酸,B=乙腈+0.1%甲酸,梯度:0%-100%B,在2.5min内;流量(ml/min)0.75。
实例P1:4-[(6-氯-3-吡啶基)甲基]-1-苯基-咪唑并[4,5-b]吡啶-2-酮(化合物A34)的制备。
步骤A:1,3-二氢-[1,2,5]噻二唑并[3,4-b]吡啶2,2-二氧化物的制备。
向2,3-二氨基吡啶(10g,87.1mmol)在吡啶(348mL)中的溶液中添加磺酰胺(12.7g,130.6mmol)并将混合物回流1.5小时。冷却后,在减压下除去吡啶并通过使用甲苯共沸蒸发除去残余吡啶,以得到粗黑色固体。通过硅胶色谱法(二氯甲烷/甲醇梯度,95:5→90:10)纯化得到呈黄色固体的1,3-二氢-[1,2,5]噻二唑并[3,4-b]吡啶2,2-二氧化物(8.6g,58%)。
1H-NMR(400MHz,DMSO-d6):δppm 7.17(dd,J=1.2,6.6Hz,1H),6.77(dd,J=1.2,7.2Hz,1H),6.49-6.42(m,1H)。
LCMS(方法A):Rt=0.16min,m/z=172(M+H+)。
步骤B:2,2-二氧代-3H-[1,2,5]噻二唑并[3,4-b]吡啶-1-甲酸叔丁酯的制备。
向1,3-二氢-[1,2,5]噻二唑并[3,4-b]吡啶2,2-二氧化物(8.6g,50.2mmol)在DMF(167mL)中的溶液中添加在石蜡油(2.2g,55.26mmol)中的60%NaH。将悬浮液在室温下搅拌1小时,并逐滴添加(Boc)2O(12.2g,55.26mmol)在DMF(40mL)中的溶液。然后将反应混合物搅拌过夜并在旋转蒸发仪中在减压下除去大部分溶剂。将残余物用乙酸乙酯(50mL)和氯化铵的饱和水溶液(50mL)稀释并用盐酸将水层的pH调节至pH=5至6。将这些相分离并将水相用乙酸乙酯(10mL)萃取并将合并的有机相用水(2×10mL)、盐水(10mL)洗涤,并用硫酸钠干燥、过滤并蒸发,以得到粗黑色残余物。通过硅胶色谱法(环己烷/乙酸乙酯梯度,1:1→0:1)纯化得到呈淡黄色固体的2,2-二氧代-3H-[1,2,5]噻二唑并[3,4-b]吡啶-1-甲酸叔丁酯(9.9g,73%)。
1H-NMR(400MHz,DMSO-d6):δppm 13.75(br s,1H),7.59(dd,J=1.2,7.4Hz,1H),7.48(dd,J=1.2,6.6Hz,1H),6.68(dd,J=6.6,7.4Hz,1H),1.54(s,9H)。
LCMS(方法A):Rt=0.75min,m/z=272(M+H+)。
步骤C:4-[(6-氯-3-吡啶基)甲基]-2,2-二氧代-[1,2,5]噻二唑并[3,4-b]吡啶-1-甲酸叔丁酯的制备。
向2,2-二氧代-3H-[1,2,5]噻二唑并[3,4-b]吡啶-1-甲酸叔丁酯(9.1g,33.6mmol)在DMF(134mL)中的溶液中添加碳酸钾(13.9g,100.7mmol)和2-氯-5-(氯甲基)吡啶(10.88g,67.16mmol)。将所得混合物在室温下搅拌过夜并用水(100mL)淬灭。将水相用乙酸乙酯(2×30mL)萃取,将合并的有机相用水(2×10mL)、盐水(10mL)洗涤,并用硫酸钠干燥、过滤并蒸发。通过硅胶色谱法(环己烷/乙酸乙酯梯度,1:1→0:1)纯化得到呈淡黄色固体的4-[(6-氯-3-吡啶基)甲基]-2,2-二氧代-[1,2,5]噻二唑并[3,4-b]吡啶-1-甲酸叔丁酯(11.48g,86%)。
1H-NMR(400MHz,DMSO-d6):δppm 8.50(d,J=2.6Hz,1H),7.88–7.83(m,2H),7.62–7.55(m,2H),6.79(s,1H),5.40(s,2H),1.54(s,9H)。
LCMS(方法A):Rt=0.94min,m/z=397(M+H+)。
步骤D:4-[(6-氯-3-吡啶基)甲基]-1H-[1,2,5]噻二唑并[3,4-b]吡啶2,2-二氧化物的制备。
在配备有冷凝器的三颈200mL烧瓶中装入在MeOH(300mL)中的4-[(6-氯-3-吡啶基)甲基]-2,2-二氧代-[1,2,5]噻二唑并[3,4-b]吡啶-1-甲酸叔丁酯(13.7g,33.1mmol)。逐滴并小心添加乙酰氯(7.17mL,99.4mmol)(在添加过程中气体析出)并将所得黄色悬浮液在65℃下搅拌4小时。将反应混合物蒸发,以得到呈米色固体的4-[(6-氯-3-吡啶基)甲基]-1H-[1,2,5]噻二唑并[3,4-b]吡啶2,2-二氧化物(10.7g,100%),将其不经任何进一步纯化而用于下一步骤。
1H-NMR(400MHz,DMSO-d6):δppm 11.29(br s,1H),8.50(d,J=2.3Hz,1H),7.86(dd,J=2.3,8.5Hz,1H),7.57(dd,J=1.1,7.1Hz,1H),7.56(d,J=8.5Hz,1H),6.77(dd,J=1.1,7.1Hz,1H),6.55(t,J=7.1Hz,1H),5.35(s,2H)。
LCMS(方法A):Rt=0.57min,m/z=297(M+1)。
步骤E:1-[(6-氯-3-吡啶基)甲基]-2-亚氨基-吡啶-3-胺的制备。
在25mL微波小瓶中装入4-[(6-氯-3-吡啶基)甲基]-1H-[1,2,5]噻二唑并[3,4-b]吡啶2,2-二氧化物(1g,2.36mmol)和37%HCl的水溶液(6mL)。将小瓶密封,并将紫色混合物在110℃下搅拌30分钟。将反应在40℃下冷却并小心将小瓶中的超压释放。将小瓶再次密封,并将橙色混合物在110℃下进一步搅拌2小时。将反应混合物在室温下冷却,倾倒在冰上并用10M NaOH的水溶液(8mL)碱化至pH 10。将水相用二氯甲烷(4×30mL)萃取,将合并的有机相用水(5mL)、盐水(5mL)洗涤,并用硫酸钠干燥、过滤并蒸发,以得到呈橙色胶状物的1-[(6-氯-3-吡啶基)甲基]-2-亚氨基-吡啶-3-胺(270mg,49%)。
1H-NMR(400MHz,DMSO-d6):δppm 8.37(d,J=2.3Hz,1H),7.74(dd,J=2.3,8.4Hz,1H),7.47(d,J=8.4Hz,1H),6.86(dd,J=1.5,7.0Hz,1H),6.25(br s,1H),6.05(dd,J=1.5,7.0Hz,1H),5.67(t,J=7.0Hz,1H),5.15-5.05(m,4H)。
LCMS(方法A):Rt=0.25min,m/z=235(M+H+)。
步骤F:4-[(6-氯-3-吡啶基)甲基]-1H-咪唑并[4,5-b]吡啶-2-酮的制备。
向在0℃冷却的1-[(6-氯-3-吡啶基)甲基]-2-亚氨基-吡啶-3-胺(715mg,2.59mmol)在二氯甲烷(30mL)中的溶液中加入碳酰氯(在甲苯中15%,2.59mL,3.63mmol)并将反应混合物在室温下搅拌过夜。然后将反应在5℃下冷却,用氨在MeOH中的7M溶液(2mL)淬灭并蒸发。通过硅胶色谱法(二氯甲烷/甲醇,90:10→80:20)纯化得到4-[(6-氯-3-吡啶基)甲基]-1H-咪唑并[4,5-b]吡啶-2-酮(600mg,90%)。
1H-NMR(400MHz,DMSO-d6):δppm 10.66(bs,1H),8.54(d,J=2.3Hz,1H),7.89(dd,J=2.3,8.4Hz,1H),7.73(dd,J=1.0,7.2Hz,1H),7.53(d,J=8.4Hz,1H),6.97(dd,J=1.0,7.2Hz,1H),6.69(t,J=7.2Hz,1H),5.49(s,2H)。
LCMS(方法A):Rt=0.30min,m/z=261(M+H+)。
步骤G:4-[(6-氯-3-吡啶基)甲基]-1-苯基-咪唑并[4,5-b]吡啶-2-酮(化合物A34)的制备。
在10mL烧瓶中装入4-[(6-氯-3-吡啶基)甲基]-1H-咪唑并[4,5-b]吡啶-2-酮(200mg,0.70mmol)、乙腈(4mL)、碘化亚铜(44.7mg,0.23mmol)、碳酸钾(268mg,1.92mmol)、N,N'-二甲基乙二胺(41mg,0.46mmol)和碘苯(237mg,1.15mmol)。烧瓶配备有冷凝器并用氩气冲洗,并将所得深灰色-蓝色悬浮液在95℃下搅拌8小时。将所述深灰色-紫色反应混合物通过硅藻土垫(其用MeOH(3×2mL)小心冲洗)并将剩余溶液蒸发。通过硅胶色谱法(二氯甲烷/甲醇梯度,100:0→90:10)纯化得到呈淡橙色固体的4-[(6-氯-3-吡啶基)甲基]-1-苯基-咪唑并[4,5-b]吡啶-2-酮(195mg,75%)。
1H-NMR(400MHz,CD3OD):δppm 8.56(d,J=2.6,1H),7.96(dd,J=2.6,8.4Hz,1H),7.85(dd,J=1.1,7.0Hz,1H),7.58–7.41(m,6H),7.27(dd,J=0.9,7.5Hz,1H),6.97–6.91(m,1H),5.66(s,2H)。
LCMS(方法A):Rt=0.75min,m/z=337(M+H+)。
实例P2:1-苯基-4-(嘧啶-5-基甲基)咪唑并[4,5-b]吡啶-2-酮(化合物A35)的制备。
步骤A:1,3-二氢咪唑并[4,5-b]吡啶-2-酮的制备。
将2-氨基吡啶-3-甲酸(CAS 5345-47-1)(10.00g,72.40mmol)分散到1,4-二噁烷(300mL)中,以获得淡棕色悬浮液。然后缓慢添加三乙胺(11.1mL,79.64mmol),随后经15分钟逐滴添加叠氮化磷酸二苯酯(16.09mL,72.40mmol)。将所得淡棕色悬浮液缓慢加热回流,并在回流下搅拌21小时30分钟并允许冷却至室温。将反应介质在减压下在40℃下浓缩,以得到棕色油状物。添加最少量的MeOH并将所形成的沉淀通过烧结的圆盘过滤漏斗过滤。将固体滤饼用Et2O洗涤并干燥,以得到1,3-二氢咪唑并[4,5-b]吡啶-2-酮。将滤液蒸发并通过色谱法纯化。将来自过滤和色谱法的固体混合,以得到1,3-二氢咪唑并[4,5-b]吡啶-2-酮。
1H NMR(400MHz,d6-DMSO):δppm 11.28(br s,1H),10.81(br s,1H),7.85(dd,J=5.32,1.28Hz,1H),7.21(dd,J=7.70,1.10Hz,1H),6.93(dd,J=7.52,5.32Hz,1H)。
LC-MS(方法A):Rt=0.19min,MS ES+=136(M+H)。
步骤B:2-氧代-3H-咪唑并[4,5-b]吡啶-1-甲酸叔丁酯的制备。
在氩气下,将1,3-二氢咪唑并[4,5-b]吡啶-2-酮(1.500g,11.10mmol)溶解在DMF(20mL)中。然后经15分钟逐份添加氢化钠(0.4662g,11.66mmol)。将所得悬浮液在室温下搅拌1小时。然后经10分钟逐滴添加溶解在DMF(16.9mL)中的二碳酸二叔丁酯(2.47g,11.10mmol),并将所获得的橙色溶液在室温下搅拌3小时。小心添加一些MeOH以淬灭反应混合物并且然后添加水。所述溶液的pH是8至9。将水层用乙酸乙酯萃取一次并将所述萃取物丢弃(除去杂质),然后用4M HCl的水溶液将pH调节至7并且用乙酸乙酯进行萃取。将合并的有机层用水(x2)洗涤,经无水硫酸钠干燥、过滤并在减压下在40℃下浓缩,以得到2-氧代-3H-咪唑并[4,5-b]吡啶-1-甲酸叔丁酯。
1H NMR(400MHz,CDCl3):δppm 8.80-10.50(br s,1H),8.13(m,1H),8.00(dd,J=7.89,1.28Hz,1H),7.10(dd,J=7.89,5.32Hz,1H),1.69(s,9H)。
LC-MS:Rt=0.75min,MS ES+=236(M+H+)。
步骤C:2-氧代-4-(嘧啶-5-基甲基)咪唑并[4,5-b]吡啶-1-甲酸叔丁酯的制备。
将2-氧代-3H-咪唑并[4,5-b]吡啶-1-甲酸叔丁酯(1.000g,4.251mmol)分散在乙腈(10.63mL)中。然后添加碳酸钾(1.780g,12.75mmol)和5-(氯甲基)嘧啶盐酸盐(0.7384g,4.251mmol)。将所得悬浮液在室温下搅拌4小时,然后回流17小时30分钟。允许所述温度在室温下冷却,并添加0.5当量的另外的5-(氯甲基)嘧啶盐酸盐(0.369g,2.125mmol)。将所得混合物在回流下搅拌1小时30分钟。在室温下冷却后,将反应介质在减压下在40℃下浓缩,并将粗材料通过硅胶色谱法纯化,以得到2-氧代-4-(嘧啶-5-基甲基)咪唑并[4,5-b]吡啶-1-甲酸叔丁酯。
1H NMR(400MHz,CDCl3):δppm 9.24(s,1H),8.90(s,2H),7.73(dd,J=7.33-1.1Hz,1H),7.31(dd,J=6.96-1.1Hz,1H),6.74(t,J=6.97Hz,1H),5.51(s,2H),1.65(s,9H)。
LC-MS:Rt=0.65min,MS ES+=328(M+H+)。
步骤D:4-(嘧啶-5-基甲基)-1H-咪唑并[4,5-b]吡啶-2-酮的制备。
将2-氧代-4-(嘧啶-5-基甲基)咪唑并[4,5-b]吡啶-1-甲酸叔丁酯(0.304g,0.929mmol)溶解在二氯甲烷(1.86mL)中。然后用注射器缓慢添加三氟乙酸(TFA)(0.358mL,4.64mmol)。观察到气体释放。将所得混合物在室温下搅拌5小时并且然后在减压下在40℃下浓缩。将所获得的残余物通过硅胶色谱法纯化,以得到4-(嘧啶-5-基甲基)-1H-咪唑并[4,5-b]吡啶-2-酮。
1H NMR(400MHz,d6-DMSO):δppm 10.98(br s,1H),9.17(s,1H),8.92(s,2H),7.89(d,J=6.24Hz,1H),7.15(d,J=6.97Hz,1H),6.86(t,J=6.97Hz,1H),5.56(s,2H)。
LC-MS:Rt=0.17min,MS ES+=228(M+H+)。
步骤E:1-苯基-4-(嘧啶-5-基甲基)咪唑并[4,5-b]吡啶-2-酮的合成。
将4-(嘧啶-5-基甲基)-1H-咪唑并[4,5-b]吡啶-2-酮(0.200g,0.880mmol)分散在乙腈(4.40mL)中。然后添加碘化亚铜(0.0513g,0.264mmol)和碳酸钾(0.307g,2.20mmol)并将所得悬浮液用氩气吹扫5分钟。然后添加1,2-二甲基乙二胺(DMEDA)(0.0574mL,0.528mmol)和碘苯(0.272g,0.149mL,1.32mmol)并将所得悬浮液在回流下搅拌5小时30分钟。在室温下冷却后,将反应混合物通过硅藻土过滤并将固体滤饼用MeOH(x3)洗涤。将滤液在减压下在40℃下浓缩。将所获得的粗材料通过硅胶色谱法纯化,以得到1-苯基-4-(嘧啶-5-基甲基)咪唑并[4,5-b]吡啶-2-酮。
1H NMR(400MHz,MeOD):δppm 9.15(s,1H),8.99(s,2H),7.92(dd,J=6.79,0.92Hz,1H),7.50-7.60(m,4H),7.43-7.47(m,1H),7.29(dd,J=7.34,1.10Hz,1H),6.97(t,J=6.91Hz,1H),5.70(s,2H)。
LC-MS:Rt=0.59min,MS ES+=304(M+H+)。
实例P3:4-[(2-氯噻唑-5-基)甲基]-5-甲基-1-苯基-咪唑并[4,5-b]吡啶-2-酮(化合物A90)的制备。
步骤A:5-甲基-1,3-二氢咪唑并[4,5-b]吡啶-2-酮的制备。
将2-氨基-6-甲烟碱酸(CAS 846021-26-9)(5.00g,31.9mmol)分散在1,4-二噁烷(150mL)中,呈棕色悬浮液。然后缓慢添加三乙胺(4.89mL,35.1mmol),随后经5分钟逐滴添加叠氮化磷酸二苯酯(7.08mL,31.9mmol)。使所得棕色悬浮液缓慢地至回流,在回流下搅拌3小时30分钟并且然后在室温下冷却。通过TLC和LC-MS监测所述反应。将反应介质在减压下在40℃下浓缩,以得到棕色油状物。将所获得的残余物通过硅胶色谱法纯化,以得到5-甲基-1,3-二氢咪唑并[4,5-b]吡啶-2-酮。
1H NMR(400MHz,d6-DMSO):δppm 11.13(br s,1H),10.65(br s,1H),7.10(d,J=7.70Hz,1H),6.78(d,J=7.70Hz,1H),2.36(s,3H)。
LC-MS:Rt=0.25min,MS ES+=150(M+H+)。
步骤B:5-甲基-2-氧代-3H-咪唑并[4,5-b]吡啶-1-甲酸叔丁酯的制备。
将5-甲基-1,3-二氢咪唑并[4,5-b]吡啶-2-酮(2.1411g,14.355mmol)溶解在DMF(30mL)中,并在室温下经20分钟逐份添加氢化钠(0.6029g,15.073mmol)。将所得混合物在室温下搅拌1小时。经15分钟逐滴添加溶解在DMF(20mL)中的二碳酸二叔丁酯(3.20g,14.355mmol)。将反应混合物在室温下剧烈搅拌5小时。通过TLC和LC-MS监测所述反应。小心添加甲醇以淬灭反应介质并且然后添加水(pH=8-9)。将水层用乙酸乙酯萃取一次并丢弃,以除去杂质。然后用4M HCl的水溶液将pH调解至7并且将水层用乙酸乙酯萃取。将合并的有机层用水洗涤,经无水硫酸钠干燥、过滤并在减压下在40℃下浓缩,以得到5-甲基-2-氧代-3H-咪唑并[4,5-b]吡啶-1-甲酸叔丁酯。
1H NMR(400MHz,CDCl3):δppm 11.0-12.0(br s,1H),7.87(d,J=8.07Hz,1H),6.92(d,J=8.07Hz,1H),2.66(s,3H),1.68(s,9H)。
LC-MS:Rt=0.81min,MS ES+=250(M+H+)。
步骤C:4-[(2-氯噻唑-5-基)甲基]-5-甲基-2-氧代-咪唑并[4,5-b]吡啶-1-甲酸叔丁酯的制备。
在室温下在25mL单颈圆底烧瓶中装入溶解在DMF(10.0mL)中的5-甲基-2-氧代-3H-咪唑并[4,5-b]吡啶-1-甲酸叔丁酯(1.00g,4.01mmol)。然后添加碳酸钾(1.12g,8.02mmol)和2-氯-5-(氯甲基)噻唑(CAS 105827-91-6)(0.674g,4.01mmol)。将所得黄色悬浮液在室温下搅拌5小时直至反应完全。将水添加到反应介质中并将水层用乙酸乙酯萃取。将合并的有机层用水(x 2)、盐水洗涤,经干硫酸钠干燥、过滤并在减压下在40℃下浓缩。将粗品通过硅胶色谱法纯化,以得到4-[(2-氯噻唑-5-基)甲基]-5-甲基-2-氧代-咪唑并[4,5-b]吡啶-1-甲酸叔丁酯。
1H NMR(400MHz,CDCl3):δppm 7.62(s,1H),7.59(d,J=7.70Hz,1H),6.52(d,J=7.70Hz,1H),5.65(s,2H),2.61(s,3H),1.66(s,9H)。
LC-MS:Rt=0.86min,MS ES+=381/383(M+H+)。
步骤D:4-[(2-氯噻唑-5-基)甲基]-5-甲基-1H-咪唑并[4,5-b]吡啶-2-酮的制备。
在室温下在5mL单颈圆底烧瓶中装入溶解在二氯甲烷(0.5mL)中的4-[(2-氯噻唑-5-基)甲基]-5-甲基-2-氧代-咪唑并[4,5-b]吡啶-1-甲酸叔丁酯(0.0517g,0.136mmol)(呈淡黄色溶液)。然后用注射器缓慢添加三氟乙酸(0.0523mL,0.679mmol)。将所得混合物在室温下搅拌2小时。将反应混合物在减压下在40℃下浓缩,以得到4-[(2-氯噻唑-5-基)甲基]-5-甲基-1H-咪唑并[4,5-b]吡啶-2-酮。
1H NMR(400MHz,CDCl3):δppm 7.79(d,J=7.70Hz,1H),7.69(s,1H),7.17(d,J=7.70Hz,1H),5.97(s,2H),2.82(s,3H)。
LC-MS:Rt=0.53min,MS ES+=281/283(M+H+)。
步骤E:4-[(2-氯噻唑-5-基)甲基]-5-甲基-1-苯基-咪唑并[4,5-b]吡啶-2-酮的制备。
将4-[(2-氯噻唑-5-基)甲基]-5-甲基-1H-咪唑并[4,5-b]吡啶-2-酮(0.070g,0.25mmol)溶解在乙腈(2.5mL)中,随后添加碘化亚铜(0.015g,0.075mmol)和碳酸钾(0.087g,0.62mmol)。将所得黄色悬浮液用氩气吹扫5分钟并添加DMEDA(0.016mL,0.15mmol)和碘苯(0.042mL,0.37mmol)。将所得悬浮液在回流下搅拌2小时并在室温下冷却。通过TLC和LC-MS监测所述反应。完成后,将水添加到反应介质中并将水层用乙酸乙酯(3x)萃取。将合并的有机层用盐水洗涤,经干硫酸钠干燥、过滤并在减压下在40℃下浓缩。将粗材料通过硅胶色谱法纯化,以得到4-[(2-氯噻唑-5-基)甲基]-5-甲基-1-苯基-咪唑并[4,5-b]吡啶-2-酮。
1H NMR(400MHz,CDCl3):δppm 7.69(s,1H),7.44-7.53(m,4H),7.30-7.37(m,1H),6.99(d,J=7.70Hz,1H),6.52(d,J=7.70Hz,1H),5.77(s,2H),2.65(s,3H)。
LC-MS:Rt=0.82min,MS ES+=357/359(M+H+)。
实例P4:4-[(2-氯噻唑-5-基)甲基]-1-苯基-咪唑并[4,5-b]吡啶-2-酮(化合物A36)的制备。
步骤A:4-[(2-氯噻唑-5-基)甲基]-2-氧代-咪唑并[4,5-b]吡啶-1-甲酸叔丁酯的制备。
将2-氧代-3H-咪唑并[4,5-b]吡啶-1-甲酸叔丁酯(1.00g,4.25mmol)分散在乙腈(21.3mL)中。然后添加碳酸钾(1.19g,8.50mmol)和2-氯-5-(氯甲基)噻唑(CAS 105827-91-6)(0.714g,4.25mmol)。将所得悬浮液在室温下搅拌19小时,然后在回流下搅拌2小时30分钟。在室温下冷却后,将水添加到反应介质中并将水层用乙酸乙酯萃取。将合并的有机层用盐水洗涤,经干硫酸钠干燥、过滤并蒸发。将粗材料通过色谱法纯化。
1H NMR(400MHz,CDCl3):δppm 7.70(dd,J=7.52,0.92Hz,1H),7.67-7.69(m,1H),7.27-7.30(m,1H),6.72(t,J=6.95Hz,1H),5.54-5.57(m,2H),1.66(s,9H)。
LC-MS:Rt=0.81min,MS ES+=367/369(M+H+)。
步骤B:4-[(2-氯噻唑-5-基)甲基]-1H-咪唑并[4,5-b]吡啶-2-酮的制备。
将4-[(2-氯噻唑-5-基)甲基]-2-氧代-咪唑并[4,5-b]吡啶-1-甲酸叔丁酯(0.3340g,0.9106mmol)溶解在二氯甲烷(1mL)中并且然后用注射器缓慢添加TFA(0.3508mL,4.553mmol)。将所得混合物在室温下搅拌5小时。将反应混合物在减压下在40℃下浓缩并将粗材料通过硅胶色谱法纯化,以得到4-[(2-氯噻唑-5-基)甲基]-1H-咪唑并[4,5-b]吡啶-2-酮。
1H NMR(400MHz,d6-DMSO):δppm 10.84(br s,1H),7.86(s,1H),7.76(d,J=6.24Hz,1H),7.05(d,J=6.97Hz,1H),6.76(t,J=6.97Hz,1H),5.65(s,2H)。
LC-MS:Rt=0.37min,MS ES+=267/269(M+H+)。
步骤C:4-[(2-氯噻唑-5-基)甲基]-1-苯基-咪唑并[4,5-b]吡啶-2-酮的制备。
在氩气下,将4-[(2-氯噻唑-5-基)甲基]-1H-咪唑并[4,5-b]吡啶-2-酮(0.070g,0.26mmol)分散在乙腈(4mL)中,随后添加碘化亚铜(0.015g,0.079mmol)和碳酸钾(0.092g,0.66mmol)。将所得米色悬浮液用氩气吹扫5分钟。然后添加DMEDA(0.017mL,0.16mmol)和碘苯(0.044mL,0.39mmol)并将所得悬浮液在回流下搅拌1小时30分钟。在室温下冷却后,将水添加到反应介质中并用乙酸乙酯(x3)进行萃取。将合并的有机层用盐水洗涤,经干硫酸钠干燥、过滤并在减压下在40℃下浓缩。将粗材料通过硅胶色谱法纯化,以得到4-[(2-氯噻唑-5-基)甲基]-1-苯基-咪唑并[4,5-b]吡啶-2-酮。
1H NMR(400MHz,CDCl3):δppm 7.73(s,1H),7.48-7.56(m,4H),7.34-7.42(m,1H),7.27(d,1H),7.02(d,1H),6.68(t,1H),5.64(s,2H)。
LC-MS:Rt=0.77min,MS ES+=343/345(M+H+)。
实例P5:化合物A41至A80的制备。
向4-[(2-氯噻唑-5-基)甲基]-1H-咪唑并[4,5-b]吡啶-2-酮(根据实例P4,步骤B制备)(0.03mmol)在1mL N,N-二甲基甲酰胺(DMF)中的溶液中添加碳酸钾K2CO3(3.0当量)、碘化亚铜(I)(0.3当量)、反式-N,N′-二甲基环己烷-1,2-二胺(1.0当量)和合适的芳基碘或芳基溴(1当量)。将混合物在140℃下进行微波辐射15分钟。将DMF蒸发并将残余物溶解在乙酸乙酯中。添加EDTA溶液(在水中12%),并且将水相用乙酸乙酯萃取3次。将有机相合并并在真空下蒸发。将希望的化合物通过HPLC进行分离并通过LC-MS(方法B)进行鉴定。
化合物A1至A102可以通过类似于实例P1至P5中所述的反应来制备。
表A:所述表披露了具有式(I)的化合物:
生物学实例:
烟粉虱(Bemisia tabaci)(棉粉虱):喂养/接触活性
将棉花叶圆片置于24孔微量滴定板中的琼脂上并且用从10,000ppm DMSO储备溶液中制备的水性测试溶液进行喷雾。在干燥之后,将叶圆片用成年粉虱进行侵染。孵育6天之后,针对死亡率对这些样品进行检查。
以下化合物在200ppm施用率下产生至少80%的死亡率:
A3、A13、A39、A62、A63、A66、A70、A80、A83、A85、A88、A92、A93、A94、A96、A100、A101、A102。
桃蚜(Myzus persicae)(绿桃蚜):喂养/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10,000ppm DMSO储备溶液制备的水性测试溶液进行喷雾。在干燥之后,将这些叶圆片用混合年龄的蚜虫群体进行侵染。侵染6天之后,针对死亡率对这些样品进行评估。
以下化合物在200ppm施用率下产生至少80%的死亡率:
A1、A2、A3、A5、A6、A7、A8、A9、A10、A11、A13、A14、A21、A23、A25、A26、A29、A30、A32、A33、A34、A36、A38、A39、A40、A42、A62、A63、A66、A67、A79、A80、A81、A82、A83、A85、A87、A88、A92、A93、A94、A95、A96、A97、A98、A99、A100、A101、A102。
桃蚜(绿桃蚜)。内吸活性
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测试比率下得到至少80%的死亡率:
A2、A3、A16、A22、A24、A25、A26、A27、A31、A32、A33、A34、A40、A82、A83、A85、A88、A92、A93、A94、A95、A96、A97、A98、A99、A100、A102。
桃蚜(绿桃蚜)。内在活性
将从10,000ppm DMSO储备溶液制备的测试化合物通过移液管施用到24孔微量滴定板中并与蔗糖溶液混合。用拉伸的石蜡膜(Parafilm)封闭板。将具有24个孔的塑料模板放置在板上,并将侵染的豌豆幼苗直接放置在石蜡膜上。用凝胶吸印纸和另一个塑料模板封闭侵染的板,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测试比率下得到至少80%的死亡率:
A1、A2、A3、A5、A6、A7、A8、A9、A10、A11、A13、A14、A16、A19、A21、A22、A24、A25、A26、A27、A29、A30、A31、A32、A33、A34、A36、A38、A39、A40、A41、A42、A47、A51、A62、A63、A66、A67、A68、A70、A71、A73、A77、A79、A80、A81、A82、A83、A85、A88、A89、A92、A93、A94、A95、A96、A97、A98、A99、A100、A101、A102。
褐稻虱(Nilaparvata lugens)(褐稻飞虱-代谢新烟碱抗性的),杀幼虫剂,喂养/接触
利用稀释的测试溶液在喷雾室中对水稻进行处理。在干燥之后,用约20N3期若虫对植物进行侵染。处理后7天,针对死亡率和生产调节对样品进行评估。
以下根据本发明的化合物在200ppm下给出了对褐稻虱的新烟碱抗性品系的至少80%的控制。
A3、A31、A33、A34、A92、A93。
烟粉虱(新烟碱抗性,棉粉虱-代谢新烟碱抗性的),成虫。
将5cm棉花叶圆片倒置于倒有11mL的0.8%水琼脂的培养皿中,并施加在转盘喷雾室中。在干燥喷雾沉积物之后,用10只成年新烟碱抗性烟粉虱侵染叶圆片。将培养皿用织物过滤器覆盖并用穿孔塑料盖密封。在浸染后4天进行对成虫死亡率%的评估。
以下化合物在200ppm下给出了对新烟碱抗性烟粉虱的至少80%的控制。
A63。
桃蚜(新烟碱抗性绿桃蚜),混合群体,接触
在喷雾室内用稀释的测试溶液处理用混合年龄的新烟碱抗性的桃蚜群体侵染的豌豆幼苗,并在处理后5天检查死亡率。
以下根据本发明的化合物在200ppm下给出了对桃蚜的新烟碱抗性品系的至少80%的控制。
A26、A30。
桃蚜(新烟碱抗性绿桃蚜),混合群体,接触/喂养。
将辣椒植物用混合年龄的新烟碱抗性蚜虫群体侵染,并在浸染后1天在喷雾室中用稀释的测试溶液进行处理。处理后5天,评估样品的死亡率。
以下描述的化合物在200ppm下给出了对桃蚜的新烟碱抗性品系的至少80%控制。
A2、A3、A63、A80、A92、A93。
桃蚜(抗性因子50(RF(50))的测试方法)。
将卷心菜叶圆片用约20-25只昆虫侵染并在波特塔(Potter Tower)中用相应的杀昆虫剂稀释进行喷雾。处理后五天评估昆虫死亡率。
RF(50)是由下式计算的:RF(50)=抗性品系的LC(50)/敏感品系的LC(50),其中LC(50)是致死浓度,其中50%的群体被控制。
根据本发明的以下化合物给了至少小于或等于25的RF(50)。
A3、A26、A30、A34、A80。
Claims (15)
1.一种具有式(I)的化合物:
其中:
W是O或S;
R1是苯基或萘基,各自任选地:(i)被独立地选自U1a的取代基单取代或多取代,(ii)被独立地选自U1b的取代基单取代或二取代,或(iii)被独立地选自U1a的取代基单取代或二取代,并且被选自U1b的取代基单取代;或者
R1是5-至12-元杂芳香族环体系或3-至12-元饱和的或部分饱和的杂环的环体系,其中所述环体系是单环的或多环的并且包含1至4个选自氮、氧和硫的杂原子,其前提是每个环体系不能含有多于2个氧或硫原子,并且其中每个环体系任选地:(i)被独立地选自U1a的取代基单取代或多取代,(ii)被独立地选自U1b的取代基单取代或二取代,或(iii)被独立地选自U1a的取代基单取代或二取代,并且被选自U1b的取代基单取代;
U1a独立地选自卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基和C1-C6卤代烷氧基;
U1b独立地选自硝基、氰基、氨基、羟基、-SCN、-CO2H、C3-C6环烷基、C3-C6卤代环烷基、C3-C6环烷基-C1-C4烷基、C3-C6卤代环烷基-C1-C4烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基-C1-C4烷氧基、氰基-C1-C4烷基、氰基-C1-C4卤代烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C1-C4卤代烷氧基-C1-C4烷基、C1-C6烷基硫烷基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、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烷基羰基、C1-C6烷氧基羰基、C1-C6卤代烷基羰基、C1-C6卤代烷氧基羰基、(C1-C6烷基)N(H)-、(C1-C6烷基)2N-、(C3-C6环烷基)N(H)-、(C3-C6环烷基)2N-、C1-C6烷基羰基氨基、C3-C6环烷基羰基氨基、C1-C6卤代烷基羰基氨基、C3-C6卤代环烷基羰基氨基、C1-C6烷基氨基羰基、C3-C6环烷基氨基羰基、C1-C6卤代烷基氨基羰基、C3-C6卤代环烷基氨基羰基、C3-C6环烷基羰基、C3-C6卤代环烷基羰基、-SF5、-NHS(O)2C1-C4烷基、甲酰基或-C(O)NH2;或者
U1b是苯基,所述苯基任选地被独立地选自U2的基团单取代或二取代;或者
U1b是5-或6-元杂芳香族环或5-或6-元饱和的或部分饱和的杂环,其中每个环包含1至4个选自氮、氧和硫的杂原子,其前提是每个环不能含有多于2个氧或硫原子,并且其中每个环任选地被独立地选自U2的基团单取代或二取代;
U2是卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、硝基、氰基、氨基、羟基、-SCN、-CO2H、C3-C6环烷基、C3-C6卤代环烷基、C3-C6环烷基-C1-C4烷基、C3-C6卤代环烷基-C1-C4烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基-C1-C4烷氧基、氰基-C1-C4烷基、氰基-C1-C4卤代烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C1-C4卤代烷氧基-C1-C4烷基、C1-C6烷基硫烷基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、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烷基羰基、C1-C6烷氧基羰基、C1-C6卤代烷基羰基、C1-C6卤代烷氧基羰基、-SF5或-C(O)NH2;
m是0、1或2;
R2独立地选自卤素、氰基、氨基、羟基、C1-C6烷基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷氧基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C3-C6环烷基、C3-C6卤代环烷基、C1-C6烷基硫烷基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基硫烷基、C1-C6卤代烷基亚磺酰基和C1-C6卤代烷基磺酰基;
R3a和R3b独立地选自氢、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基和氰基;
R4选自Y1至Y7之一;
其中,n是0、1、2、或3;
Z是氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基;并且
U3独立地选自卤素、氰基、硝基、羟基、氨基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4卤代烷氧基-C1-C4烷基、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、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、甲酰基、环丙基、C1-C6烷基羰基或C3-C6环烷基羰基;
或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物。
2.根据权利要求1所述的化合物,其中,R1是苯基,或5-或6-元杂芳香族单环的环体系,所述环体系包含1或2个氮原子或是呋喃基或噻吩基,其中每个R1任选地:
(i)被独立地选自U1a的取代基单取代或二取代,
(ii)被独立地选自U1b的取代基单取代或二取代,或
(iii)被独立地选自U1a的取代基单取代或二取代,并且被选自U1b的取代基单取代。
3.根据权利要求1或权利要求2所述的化合物,其中,R1是苯基、吡唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、噁唑基、噁二唑基、噻唑基、噻二唑基、呋喃基或噻吩基,其中R1任选地被以下取代:
(i)独立地选自U1a的1或2个取代基,其中U1a是卤素、C1-C4烷基、C1-C4氟烷基、C1-C4烷氧基以及C1-C4氟烷氧基,或
(ii)选自U1b的1个取代基,其中U1b是硝基、氰基、氨基、C3-C6环烷基、氰基C1-C4烷基、C1-C4烷基羰基、C1-C4烷氧基羰基、C1-C4卤代烷基羰基,或U1b是任选地被选自U2的取代基取代的苯基或氧杂环丁烷-3-基,其中U2是氟、氯、甲基、乙基、甲氧基、乙氧基或三氟甲基。
4.根据权利要求1至3中任一项所述的化合物,其中,R1是吡唑基,所述吡唑基任选地被独立地选自U1a的1或2个取代基或被选自U1b的单个取代基取代,其中U1a是C1-C4烷基或C1-C4氟烷基,其中U1b是C3-C4环烷基。
5.根据权利要求1至4中任一项所述的化合物,其中,m是0或1,并且优选是0。
6.根据权利要求1至5中任一项所述的化合物,其中,R3a是氢并且R3b是氢。
7.根据权利要求1至6中任一项所述的化合物,其中,R4选自Y2、Y3或Y4。
8.根据权利要求1至7中任一项所述的化合物,其中,n是0或1。
12.一种农用化学组合物,其包含杀昆虫、杀螨、杀线虫、或杀软体动物有效量的根据权利要求1至10中任一项所述的化合物。
13.根据权利要求12所述的组合物,其进一步包含至少一种另外的活性成分和/或农用化学上可接受的稀释剂或载体。
14.一种控制昆虫、螨、线虫或软体动物的方法,所述方法包括将杀昆虫、杀螨、杀线虫或杀软体动物有效量的如权利要求1至10中任一项所定义的具有式(I)的化合物、或包含此化合物作为活性成分的组合物施用到有害生物、有害生物场所(优选植物)、易受有害生物攻击的植物或其繁殖材料(如种子)。
15.根据权利要求1至10中任一项所述的化合物作为杀昆虫剂、杀螨剂、杀线虫剂或杀软体动物剂的用途。
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