CN103492378B - 杀虫吡唑化合物 - Google Patents
杀虫吡唑化合物 Download PDFInfo
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- CN103492378B CN103492378B CN201280018530.8A CN201280018530A CN103492378B CN 103492378 B CN103492378 B CN 103492378B CN 201280018530 A CN201280018530 A CN 201280018530A CN 103492378 B CN103492378 B CN 103492378B
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- FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 0.000 description 1
- 229940048914 protamine Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- DDIQWGKUSJOETH-UHFFFAOYSA-N pyrafluprole Chemical compound ClC=1C=C(C(F)(F)F)C=C(Cl)C=1N1N=C(C#N)C(SCF)=C1NCC1=CN=CC=N1 DDIQWGKUSJOETH-UHFFFAOYSA-N 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- AEHJMNVBLRLZKK-UHFFFAOYSA-N pyridalyl Chemical group N1=CC(C(F)(F)F)=CC=C1OCCCOC1=C(Cl)C=C(OCC=C(Cl)Cl)C=C1Cl AEHJMNVBLRLZKK-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- ITKAIUGKVKDENI-UHFFFAOYSA-N pyrimidifen Chemical compound CC1=C(C)C(CCOCC)=CC=C1OCCNC1=NC=NC(CC)=C1Cl ITKAIUGKVKDENI-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- MSHXTAQSSIEBQS-UHFFFAOYSA-N s-[3-carbamoylsulfanyl-2-(dimethylamino)propyl] carbamothioate;hydron;chloride Chemical compound [Cl-].NC(=O)SCC([NH+](C)C)CSC(N)=O MSHXTAQSSIEBQS-UHFFFAOYSA-N 0.000 description 1
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 208000008864 scrapie Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229940125794 sodium channel blocker Drugs 0.000 description 1
- 239000003195 sodium channel blocking agent Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- DEWVPZYHFVYXMZ-QCILGFJPSA-M sodium;(3ar,4as,8ar,8bs)-2,2,7,7-tetramethyl-4a,5,8a,8b-tetrahydro-[1,3]dioxolo[3,4]furo[1,3-d][1,3]dioxine-3a-carboxylate Chemical compound [Na+].O([C@H]12)C(C)(C)OC[C@@H]1O[C@]1(C([O-])=O)[C@H]2OC(C)(C)O1 DEWVPZYHFVYXMZ-QCILGFJPSA-M 0.000 description 1
- NZYOAGBNMCVQIV-UHFFFAOYSA-N sodium;chloro-(4-methylphenyl)sulfonylazanide;trihydrate Chemical compound O.O.O.[Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 NZYOAGBNMCVQIV-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 229940014213 spinosad Drugs 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- FKENQMMABCRJMK-RITPCOANSA-N sulbactam Chemical compound O=S1(=O)C(C)(C)[C@H](C(O)=O)N2C(=O)C[C@H]21 FKENQMMABCRJMK-RITPCOANSA-N 0.000 description 1
- 229960005256 sulbactam Drugs 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 229960004306 sulfadiazine Drugs 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 208000004441 taeniasis Diseases 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 description 1
- 235000012756 tartrazine Nutrition 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 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
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- ZOKXUAHZSKEQSS-UHFFFAOYSA-N tribufos Chemical compound CCCCSP(=O)(SCCCC)SCCCC ZOKXUAHZSKEQSS-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
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- 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
- 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
- 238000001665 trituration Methods 0.000 description 1
- 239000003744 tubulin modulator Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
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- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Catching Or Destruction (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及新的式(I)的吡唑,其中各变量如发明描述中所定义;一种防治无脊椎动物害虫的方法,一种保护植物繁殖材料和/或由其生长的植物的方法,包含至少一种本发明化合物的植物繁殖材料,和一种农业组合物。
Description
发明描述
本发明涉及新的式I的吡唑及其立体异构体、盐、互变异构体和N-氧化物:
其中,
U为N或CH;
T为O或S;
R1为H、C1-C2烷基或C1-C2烷氧基-C1-C2烷基;
R2为CH3或卤甲基;
R3为C2-C6烷基、C1-C6卤代烷基、C1-C2烷氧基-C1-C2烷基、C2-C6链烯基和C2-C6炔基、C3-C6环烷基、C5-C6环烯基、C1-C6烷氧基、CN、NO2或S(O)nRb,其中C原子可未经取代,或部分地或完全经Ra取代;
Ra为卤素、CN、NO2、C1-C2烷基、C1-C2卤代烷基、C1-C4烷氧基、C1-C2卤代烷氧基或S(O)nRb,其中n为0、1或2;
Rb为氢、C1-C2烷基、C1-C2卤代烷基、C3-C6环烷基或C1-C4烷氧基,
R4为C1-C4烷基或对R3所提及的基团;
R5为H或对R4所提及的基团;
R3和R4可一起形成3-6员碳环或杂环,其可含有1或2个选自N-Rc、O和S的杂原子,其中S可经氧化,该碳环或杂环可经Ra取代;
Rc为氢、C1-C2烷基、C1-C2卤代烷基、C1-C2烷基羰基或C1-C2烷氧基羰基。
此外,本发明涉及制备式I的吡唑的方法和中间体,以及包含其的活 性化合物组合,包含其的组合物及其在防除无脊椎动物害虫中的用途。此外,本发明涉及施加该类化合物的方法。
本发明的其他实施方案可参见权利要求、发明描述和实施例。应理解上文所提及的本发明主题的特征和下文仍要阐释的那些不仅可应用于相应给定组合中,而且可应用于其他组合中而不背离本发明范围。
WO 2009/027393、WO 2010/034737、WO 2010/034738和WO 2010/112177描述了由吡唑羧酸衍生的N-芳基酰胺衍生物。提及这些化合物可用于防除无脊椎动物害虫。
无脊椎动物害虫以及尤其是节肢动物和线虫破坏生长和收获的作物且袭击木质居住和商业结构体,从而对食物供应和财产造成大的经济损失。仍然需要用于防除无脊椎动物害虫,例如昆虫、蜘蛛和线虫的新试剂。因此,本发明的目的为提供具有良好杀虫活性并对大量不同无脊椎动物害虫,尤其对难以防治的害虫,例如昆虫显示出广谱活性的化合物。
已发现这些目的可通过如开头所定义的式I化合物及其立体异构体、盐、互变异构体和N-氧化物,尤其是其可农用盐来实现。
本发明的一个实施方案涉及式I化合物,其中U为CH。这些化合物对应于式I.A。
本发明的另一实施方案涉及式I化合物,其中U为N。这些化合物对应于式I.B。
本发明化合物可根据有机化学标准方法以与WO 2009/027393和WO 2010/034737中所述合成途径类似的方式制备,例如根据以下合成途径:
式I化合物(其中T为O)(式I.1)可通过(例如)使活化吡唑羧酸衍生物II与3-氨基吡啶或式III的4-氨基哒嗪反应来制备(例如Houben-Weyl:“Methoden der organ.Chemie”[Methods of Organic Chemistry],Georg-Thieme-Verlag,Stuttgart,New York 1985,第E5卷,第941页至第1045页)。
活化吡唑羧酸衍生物II优选为卤化物、活化酯、酸酐、氮化物,例如氯化物、氟化物、溴化物、对硝基苯基酯、五氟苯基酯、N-羟基琥珀酰亚胺、羟基苯并三唑-1-基酯。
在式II和III中,这些基团具有上文对式I所提及的含义,尤其是所提及的优选含义,X为合适离去基团,例如卤素、N3、对硝基苯氧基或五氟苯氧基等。
式I.1化合物(其中R1不为氢)还可通过在碱存在下使用合适烷基化试剂将酰胺I.1(其中R1为氢)烷基化来制备。可在由文献已知的标准条件下进行烷基化。
式I化合物可以两种异构形式存在,且式I.B化合物可以三种异构形式存在,因此式I涵盖互变异构体T-A和T-B二者,且对于式I.B,还涵盖T-C:
为清晰起见,其在整个说明书中仅称作异构体T-A,但其描述还涵盖其他异构体的公开内容。
异构体T-C可通过化合物I.B.1(其中R1为氢)烷基化来获得。该反应可以与已知哒嗪的N-烷基化类似的方式进行。哒嗪的N-烷基化于文献中已知且可参见例如:J.Chem.Soc.,Perkin Trans.第1卷,第401页(1988)和J.Org.Chem.第46卷,第2467页(1981)。
式I化合物(其中T为S)(式I.2)可根据Synthesis 2003,第1929页中所述方法(例如)通过使式I.1化合物与2,4-双(4-甲氧基苯基)-1,3,2,4-二硫杂二磷杂己环(dithiadiphosphetane)或PS5反应来制备。
化合物II和III为本领域已知或可市购或可通过由文献(参见WO 05/040169;WO08/074824;Journal of Fluorine chemistry 132(11),第995页(2011))已知的方法制备。
式I化合物的N-氧化物可根据制备杂芳族N-氧化物的标准方法通过氧化化合物I来制备,例如通过Journal of Organometallic Chemistry 1989,370,17-31中所述方法。
若不能经由上述途径制备单独化合物,则其可通过其他化合物I的衍生化或通过对所述合成途径的已知改变来制备。例如,在单独情况下,某些化合物I有利地可通过酯水解、酰胺化、酯化、醚裂解、烯化、还原、氧化等由其他化合物I来制备。
可以已知方式后处理反应混合物,例如通过与水混合、分离各相和(若合适)通过层析(例如在氧化铝或硅胶上)纯化粗产物来后处理。可以无色或浅褐色粘稠油形式获得一些中间体和终产物,其在减压和适度升高的温度下从挥发性组分中取出或由挥发性组分纯化得到。若以固体形式获得中间体和终产物,则可通过重结晶或研磨将其纯化。
术语“本发明化合物”或“式I化合物”包含如本文所定义的化合物以及其立体异构体、盐、互变异构体或N-氧化物。术语“本发明化合物(compound of the presentinvention)”应理解为等同于术语“本发明化合物(compound according to theinvention)”,因此还包含其立体异构体、盐、互变异构体或N-氧化物。
连接至式I骨架的基团可含有一个或多个手性中心。在这种情况下,式I以不同对映体或非对映体形式存在,这取决于取代基。本发明涉及式I的每一可能立体异构体,即涉及单一对映体或非对映体以及其混合物。
式I化合物可为无定形的或可以一种或多种不同晶态(多晶型)存在,其可具有不同宏观性能(例如稳定性)或显示不同生物学性能(例如活性)。本发明涉及无定形和结晶式I化合物、相应化合物I的不同晶态的混合物以及其无定形或结晶盐。
式I化合物的盐优选为可农用盐。其可以常规方式形成,例如,若式I化合物具有碱性官能基,则通过使该化合物与所述阴离子的酸反应。
式I化合物的农业上可用盐尤其涵盖其阳离子和阴离子分别对式I化合物的杀虫作用无不利影响的那些酸的酸加成盐。
可用酸加成盐的阴离子主要为氯离子、溴离子、氟离子、硫酸氢根、硫酸根、磷酸二氢根、磷酸氢根、磷酸根、硝酸根、碳酸氢根、碳酸根、六氟硅酸根、六氟磷酸根、苯甲酸根和C1-C4链烷酸的阴离子(优选为甲酸根、乙酸根、丙酸根和丁酸根)。其可通过使式I化合物与相应阴离子的酸(优选为盐酸、氢溴酸、硫酸、磷酸或硝酸)反应来形成。
术语“N-氧化物”包括任何具有至少一个氧化成N-氧化物结构部分的叔氮原子的式I化合物。
在上述变量定义中所提及的有机结构部分(例如术语卤素)为各基团成员的各次列举的集合性术语。前缀Cn-Cm在每种情况下均表示基团中可能的碳原子数。
术语“卤素”在每种情况下均表示氟、溴、氯或碘,尤其是氟、氯或溴。
本文和烷氧基、烷基羰基、烷硫基、烷基亚磺酰基、烷基磺酰基和烷氧基烷基的烷基结构部分中所用术语“烷基”在每种情况下均表示直链或支化烷基,其通常具有1-6个碳原子,优选1-4个碳原子,尤其是1-3个碳原子。烷基的实例为甲基、乙基、正丙基、异丙基、正丁基、2-丁基、异丁基、叔丁基、正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、正己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基和1-乙基-2-甲基丙基。
本文和卤代烷氧基、卤代烷硫基卤代烷基羰基、卤代烷基磺酰基和卤代烷基亚磺酰基的卤代烷基结构部分中所用术语“卤代烷基”在每种情况下均表示直链或支化烷基,其通常具有1-6个碳原子,经常具有1-4个碳原子,其中该基团的氢原子部分地或全部经卤素原子替换。优选卤代烷基结构部分选自C1-C2卤代烷基,尤其是C1-C2氟烷基,例如氟甲基、二氟甲基、三氟甲基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、五氟乙基等。
本文所用术语“烷氧基”在每种情况下均表示直链或支化烷基,其经由氧原子键合且通常具有1-6个碳原子,优选1-4个碳原子。烷氧基的实例为甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、2-丁氧基、异丁氧基、叔丁氧基等。
本文和环烷氧基和环烷基甲基的环烷基结构部分中所用术语“环烷基”在每种情况下均表示通常具有3-6个碳原子的单环环脂族基团,例如环丙基、环丁基、环戊基和环己基。
本文所用术语“链烯基”在每种情况下均表示单不饱和烃基,其通常具有2-6个,优选2-4个碳原子,例如乙烯基、烯丙基(2-丙烯-1-基)、1-丙烯-1-基、2-丙烯-2-基、甲代烯丙基(2-甲基丙-2-烯-1-基)、2-丁烯-1-基、3-丁烯-1-基、2-戊烯-1-基、3-戊烯-1-基、4-戊烯-1-基、1-甲基丁-2-烯-1-基、2-乙基丙-2-烯-1-基等。
本文所用术语“炔基”在每种情况下均表示通常具有2-6个,优选2-4个碳原子的单不饱和烃基,例如乙炔基、炔丙基(2-丙炔-1-基)、1-丙炔-1-基、1-甲基丙-2-炔-1-基)、2-丁炔-1-基、3-丁炔-1-基、1-戊炔-1-基、3-戊炔-1-基、4-戊炔-1-基、1-甲基丁-2-炔-1-基、1-乙基丙-2-炔-1-基等。
本文所用术语“烷氧基烷基”是指通常包含1-2个碳原子的烷基,其中1个碳原子带有如上文所定义通常包含1或2个碳原子的烷氧基。实例为CH2OCH3、CH2-OC2H5、2-(甲氧基)乙基和2-(乙氧基)乙基。
术语“杂环基”通常包括5员或6员,尤其是6员单环杂环非芳族基团。杂环非芳族基团通常包含1、2或3个选自N、O和S的杂原子作为环成员,其中作为环成员的S原子可以S、SO或SO2形式存在。
5或6员杂环基团的实例包括饱和或不饱和的非芳族杂环,例如环氧乙烷基、氧杂丁环基、硫杂环丁基、硫杂环丁基-S-氧化物(S-氧代硫杂环丁基)、硫杂环丁基-S-二氧化物(S-二氧代硫杂环丁基)、吡咯烷基、吡咯啉基、吡唑啉基、四氢呋喃基、二氢呋喃基、1,3-二氧戊环基、硫杂环戊基、S-氧代硫杂环戊基、S-二氧代硫杂环戊基、二氢噻吩基、S-氧代二氢噻吩基、S-二氧代二氢噻吩基、唑烷基、唑啉基、噻唑啉基、氧杂硫杂环戊基、哌啶基、哌嗪基、吡喃基、二氢吡喃基、四氢吡喃基、1,3-二烷基和1,4-二烷基、噻喃基、S-氧代噻喃基、S-二氧代噻喃基、二氢噻喃基、S-氧代二氢噻喃基、S-二氧代二氢噻喃基、四氢噻喃基、S-氧代四氢噻喃基、S-二氧代四氢噻喃基、吗啉基、硫吗啉基、S-氧代硫吗啉基、S-二氧代硫吗啉基、噻嗪基等。也包含1或2个羰基作为环成员的杂环实例包括吡咯烷-2-酮基、吡咯烷-2,5-二酮基、咪唑烷-2-酮基、唑烷-2-酮基、噻唑烷-2-酮基等。
对于变量而言,中间体的尤其优选实施方案对应于式I基团的那些。
在具体实施方案中,式I化合物的变量具有以下含义,这些含义单独和彼此组合均为式I化合物的具体实施方案:
在式I化合物的一个优选实施方案中,U为CH。这些化合物对应于式I.A。
在式I化合物的另一实施方案中,U为N。这些化合物对应于式I.B。
在式I的第一优选实施方案中,T为O。这些化合物对应于式I.1。
在式I的另一实施方案中,T为S。这些化合物对应于式I.2。
在第一实施方案中,R1为H。
在另一实施方案中,R1为C1-C2烷基,优选为CH3。
在另一实施方案中,R1为CH2CH3。
在另一实施方案中,R1为C1-C2烷氧基-C1-C2烷基,优选为C1-C2烷氧基甲基,尤其是CH2OCH3。
在第一实施方案中,R2为CH3。
在另一实施方案中,R2为卤甲基,优选为氟甲基,尤其是CHF2或CF3。
在第一优选实施方案中,R3为C2-C6烷基,优选为C2-C4烷基,尤其是CH2CH3或C(CH3)3。
在另一优选实施方案中,R3为C1-C6卤代烷基,优选为C1-C2烷基,更优选为甲基,例如CHF2或CF3,尤其是CF3。
在另一优选实施方案中,R3为C1-C2烷氧基-C1-C2烷基,优选为C1-C2烷氧基甲基,尤其是CH2OCH3。
在另一优选实施方案中,R3为C3-C6环烷基,优选为环丙基,其未经取代或经取代,优选经卤素或氰基取代。取代基优选位于1-位或2,2-位。
在第一优选实施方案中,R4为C1-C4烷基,优选为C1-C2烷基,尤其是CH3。
在另一优选实施方案中,R4为C1-C6卤代烷基,优选为C1-C2烷基,尤其是卤甲基,例如CF3。
在另一实施方案中,R4为C3-C6环烷基,优选为环丙基,其可经取代,优选经卤素或氰基取代。取代基优选位于1-位或2,2-位。
在第一优选实施方案中,R5为氢。
在另一优选实施方案中,R5为CN或NO2,优选为CN。
在另一优选实施方案中,R5为C1-C4烷基,优选为C1-C2烷基,尤其是CH3。
在另一实施方案中,R3和R4形成5或6员饱和碳环,例如环戊基或环己基,其未经取代或经一个或多个基团Ra取代。这些Ra基团优选为卤素、氰基或卤甲基。
在另一实施方案中,R3和R4形成5或6员饱和杂环,其含有1或2个,优选1个选自N-Rc、O和S的杂原子,其中S可经氧化,该杂环未经取代或经一个或多个基团Rd取代。
Rc优选表示C1-C2烷基,尤其是CH3;或C1-C2烷基羰基,尤其是乙酰基。
该杂环优选未经取代。
在一个实施方案中,由R3和R4形成的杂环代表基团H:
其中G为N-Rc、O、S、S(=O)或SO2,且#表示至吡唑结构部分的键。
另一实施方案涉及式I化合物,该式I化合物不包括其中T为O,R1为H、C1-C2烷基或CH2OCH3,R2为CH3、CHF2或CF3,R3为CF3或环丙基,R4为CH3,且R5为H的外消旋化合物。
尤其考虑到其用途,优选下表中所汇编的式I化合物,这些化合物对应于式I.1。此外,对表中取代基所提及的基团中的每一个本身(与提及该基团的组合无关)为所述取代基的尤其优选方面。
表1
式I.1化合物,其中U为CH,R1为H,R2为CH3且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表2
式I.1化合物,其中U为N,R1为H,R2为CH3且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表3
式I.1化合物,其中U为CH,R1为H,R2为CHF2且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表4
式I.1化合物,其中U为N,R1为H,R2为CHF2且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表5
式I.1化合物,其中U为CH,R1为H,R2为CF3且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表6
式I.1化合物,其中U为N,R1为H,R2为CF3且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表7
式I.1化合物,其中U为CH,R1和R2为CH3且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表8
式I.1化合物,其中U为N,R1和R2为CH3且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表9
式I.1化合物,其中U为CH,R1为CH3,R2为CHF2且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表10
式I.1化合物,其中U为N,R1为CH3,R2为CHF2且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表11
式I.1化合物,其中U为CH,R1为CH3,R2为CF3且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表12
式I.1化合物,其中U为N,R1为CH3,R2为CF3且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表13
式I.1化合物,其中U为CH,R1为CH2CH3,R2为CH3且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表14
式I.1化合物,其中U为N,R1为CH2CH3,R2为CH3且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表15
式I.1化合物,其中U为CH,R1为CH2CH3,R2为CHF2且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表16
式I.1化合物,其中U为N,R1为CH2CH3,R2为CHF2且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表17
式I.1化合物,其中U为CH,R1为CH2CH3,R2为CF3且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表18
式I.1化合物,其中U为N,R1为CH2CH3,R2为CF3且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表19
式I.1化合物,其中U为CH,R1为CH2OCH3,R2为CH3且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表20
式I.1化合物,其中U为N,R1为CH2OCH3,R2为CH3且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表21
式I.1化合物,其中U为CH,R1为CH2OCH3,R2为CHF2且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表22
式I.1化合物,其中U为N,R1为CH2OCH3,R2为CHF2且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表23
式I.1化合物,其中U为CH,R1为CH2OCH3,R2为CF3且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表24
式I.1化合物,其中U为N,R1为CH2OCH3,R2为CF3且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表25
式I.1化合物,其中U为CH,R1为CH2OCH2CH3,R2为CH3且R3、 R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表26
式I.1化合物,其中U为N,R1为CH2OCH2CH3,R2为CH3且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表27
式I.1化合物,其中U为CH,R1为CH2OCH2CH3,R2为CHF2且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表28
式I.1化合物,其中U为N,R1为CH2OCH2CH3,R2为CHF2且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表29
式I.1化合物,其中U为CH,R1为CH2OCH2CH3,R2为CF3且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表30
式I.1化合物,其中U为N,R1为CH2OCH2CH3,R2为CF3且R3、R4和R5的组合对化合物而言在每种情况下对应于表A的一行
表A
由于本发明化合物的优异活性,其可用于防治无脊椎动物害虫。
因此,本发明还提供防治无脊椎动物害虫的方法,该方法包括用杀虫有效量的如上文所定义的本发明化合物或组合物处理害虫、其食物供应源、其栖息地或其繁殖地;或其中害虫生长或可能生长的栽培植物、植物繁殖材料(例如种子)、土壤、区域、材料或环境;或要防止受到害虫侵袭或侵染的材料、栽培植物、植物繁殖材料(例如种子)、土壤、表面或空间。
本发明还涉及保护生长中的植物以防无脊椎动物害虫,优选昆虫种群侵袭或侵染的方法,该方法包括使植物、或其中植物生长或可能生长的土壤或水与杀虫有效量的至少一种本发明化合物(包括其立体异构体、盐、互变异构体或N-氧化物)或本发明组合物接触。
优选地,本发明方法用于保护植物繁殖材料(例如种子)和由其生长的植物以防无脊椎动物害虫侵袭或侵染,且包括用杀虫有效量的如上文所定义的本发明化合物或用杀虫有效量的如上文和下文中所定义的农业组合物处理植物繁殖材料(例如种子)。本发明方法并不限于对已根据本发明处理的“底物”(植物、植物繁殖材料、土壤材料等)的保护,且由此对由经处理植物繁殖材料(例如种子)生长的植物还具有预防性效果(例如保护),其中该植物自身未经处理。
就本发明而言,“无脊椎动物害虫”优选选自节肢动物和线虫,更优选选自有害昆虫、蜘蛛和线虫,甚至更优选选自昆虫、螨虫和线虫。在本发明的含义中,“无脊椎动物害虫”最优选为昆虫。
本发明化合物(包括其盐、立体异构体和互变异构体)尤其适于有效地防治节肢害虫,例如蜘蛛、多足虫(myriapede)和昆虫以及线虫,尤其是昆虫。其尤其适于有效地防治或防治以下害虫:
鳞翅目昆虫(鳞翅目(Lepidoptera)),例如小地老虎(Agrotis ypsilon)、黄地老虎(Agrotis segetum)、木棉虫(Alabama argillacea)、黎豆夜蛾(Anticarsiagemmatalis)、Argyresthia conjugella、叉纹夜蛾(Autographa gamma)、树尺蠖(Bupaluspiniarius)、Cacoecia murinana、Capua reticulana、Cheimatobia brumata、云杉色卷蛾(Choristoneura fumiferana)、Choristoneura occidentalis、二化螟(Cirphisunipuncta)、苹果小卷蛾(Cydia pomonella)、松毛虫(Dendrolimus pini)、Diaphanianitidalis、西南玉米杆草螟(Diatraea grandiosella)、埃及钻夜蛾(Earias insulana)、南美玉米苗斑螟(Elasmopalpus lignosellus)、女贞细卷蛾(Eupoecilia ambiguella)、Evetria bouliana、Feltia subterranea、蜡螟(Galleria mellonella)、李小食心虫(Grapholitha funebrana)、梨小食心虫(Grapholitha molesta)、棉铃虫(Heliothisarmigera)、烟芽夜蛾(Heliothis virescens)、玉米穗虫(Heliothis zea)、菜螟(Hellulaundalis)、Hibernia defoliaria、美国白蛾(Hyphantria cunea)、苹果巢蛾(Hyponomeutamalinellus)、番茄虫蛾(Keiferia lycopersicella)、Lambdina fiscellaria、甜菜夜蛾(Laphygma exigua)、咖啡潜叶蛾(Leucoptera coffeella)、旋纹潜蛾(Leucopterascitella)、Lithocolletis blancardella、葡萄浆果小卷蛾(Lobesia botrana)、甜菜网螟(Loxostege sticticalis)、舞毒蛾(Lymantria dispar)、模毒蛾(Lymantria monacha)、桃潜蛾(Lyonetia clerkella)、黄褐天幕毛虫(Malacosoma neustria)、甘蓝夜蛾(Mamestrabrassicae)、黄杉毒蛾(Orgyia pseudotsugata)、玉米螟(Ostrinia nubilalis)、小眼夜蛾(Panolis flammea)、棉花红铃虫(Pectinophora gossypiella)、疆夜蛾(Peridromasaucia)、圆掌舟蛾(Phalera bucephala)、马铃薯麦蛾(Phthorimaea operculella)、柑桔潜叶蛾(Phyllocnistis citrella)、欧洲粉蝶(Pieris brassicae)、苜蓿绿夜蛾(Plathypena scabra)、菜蛾(Plutella xylostella)、大豆夜蛾(Pseudoplusiaincludens)、Rhyacionia frustrana、Scrobipalpula absoluta、麦蛾(Sitotrogacerealella)、葡萄卷叶蛾(Sparganothis pilleriana)、草地夜蛾(Spodopterafrugiperda)、海灰翅夜蛾(Spodoptera littoralis)、斜纹夜蛾(Spodoptera litura)、Thaumatopoea pityocampa、绿色橡木飞蛾(Tortrix viridana)、粉纹夜蛾(Trichoplusiani)和Zeiraphera canadensis;
甲虫(鞘翅目(Coleoptera)),例如梨窄吉丁(Agrilus sinuatus)、直条叩头虫(Agriotes lineatus)、暗色叩头虫(Agriotes obscurus)、Amphimallus solstitialis、Anisandrus dispar、墨西哥棉铃象(Anthonomus grandis)、苹 花象(Anthonomuspomorum)、Aphthona euphoridae、Athous haemorrhoidalis、甜菜隐食甲(Atomarialinearis)、纵坑切梢小蠹(Blastophagus piniperda)、Blitophaga undata、蚕豆象(Bruchus rufimanus)、豌豆象(Bruchus pisorum)、欧洲兵豆象(Bruchus lentis)、苹卷象(Byctiscus betulae)、甜菜大龟甲(Cassida nebulosa)、Cerotoma trifurcata、金花金龟(Cetonia aurata)、白菜籽龟象(Ceuthorrhynchus assimilis)、芫菁龟象(Ceuthorrhynchus napi)、甜菜胫跳甲(Chaetocnema tibialis)、Conoderusvespertinus、石刁柏负泥虫(Crioceris asparagi)、Ctenicera ssp.、长角叶甲(Diabrotica longicornis)、Diabrotica semipunctata、Diabrotica 12-punctata、南美叶甲(Diabrotica speciosa)、玉米根叶甲(Diabrotica virgifera)、墨西哥豆瓢虫(Epilachna varivestis)、烟草跳甲(Epitrix hirtipennis)、棉灰蒙象变种(Eutinobothrus brasiliensis)、欧洲松树皮象(Hylobius abietis)、埃及苜蓿叶象(Hypera brunneipennis)、紫苜蓿叶象(Hypera postica)、云杉八齿小蠹(Ipstypographus)、烟草负泥虫(Lema bilineata)、黑角负泥虫(Lema melanopus)、马铃薯叶甲(Leptinotarsa decemlineata)、Limonius californicus、稻水象甲(Lissorhoptrusoryzophilus)、Melanotus communis、油菜露尾甲(Meligethes aeneus)、大栗鳃金龟(Melolontha hippocastani)、五月鳃金龟(Melolontha melolontha)、水稻负泥虫(Oulemaoryzae)、葡萄黑耳喙象(Ortiorrhynchus sulcatus)、草莓根象甲(Otiorrhynchusovatus)、辣根猿叶甲(Phaedon cochleariae)、梨树叶象(Phyllobius pyri)、Phyllotretachrysocephala、食叶鳃金龟属(Phyllophaga sp.)、庭园发丽金龟(Phylloperthahorticola)、大豆淡足跳甲(Phyllotreta nemorum)、黄曲条菜跳甲(Phyllotretastriolata)、日本金龟子(Popillia japonica)、豌豆叶象(Sitona lineatus)和谷象(Sitophilus granaria);
蝇、蚊(双翅目(Diptera)),例如埃及伊蚊(Aedes aegypti)、白纹伊蚊(Aedesalbopictus)、剌扰伊蚊(Aedes vexans)、墨西哥果蝇(Anastrepha ludens)、五斑按蚊(Anopheles maculipennis)、Anopheles crucians、白足按蚊(Anopheles albimanus)、冈比亚按蚊(Anopheles gambiae)、 Anopheles freeborni、海南岛白踝按蚊(Anophelesleucosphyrus)、云南微小按蚊(Anopheles minimus)、四斑按蚊(Anophelesquadrimaculatus)、红头丽蝇(Calliphora vicina)、地中海实蝇(Ceratitis capitata)、蛆症金蝇(Chrysomya bezziana)、Chrysomya hominivorax、Chrysomya macellaria、鹿蝇(Chrysops discalis)、Chrysops silacea、Chrysops atlanticus、螺旋蝇(Cochliomyiahominivorax)、高粱瘿蚊(Contarinia sorghicola)、嗜人瘤蝇蛆(Cordylobiaanthropophaga)、狂怒库蠓(Culicoides furens)、尖音库蚊(Culex pipiens)、斑蚊(Culexnigripalpus)、致倦库蚊(Culex quinquefasciatus)、媒斑蚊(Culex tarsalis)、Culisetainornata、Culiseta melanura、瓜蝇(Dacus cucurbitae)、油橄榄实蝇(Dacus oleae)、油菜叶瘿蚊(Dasineura brassicae)、Delia antique、麦地种蝇(Delia coarctata)、灰地种蝇(Delia platura)、甘蓝地种蝇(Delia radicum)、Dermatobia hominis、小毛厕蝇(Fannia canicularis)、Geomyza Tripunctata、马蝇(Gasterophilus intestinalis)、刺舌蝇(Glossina morsitans)、须舌蝇(Glossina palpalis)、Glossina fuscipes、胶舌蝇(Glossina tachinoides)、Haematobia irritans、Haplodiplosis equestris、潜蝇属(Hippelates spp.)、花生田灰地种蝇(Hylemyia platura)、纹皮蝇(Hypoderma lineata)、Leptoconops torrens、蔬菜斑潜蝇(Liriomyza sativae)、美国潜叶蝇(Liriomyzatrifolii)、Lucilia caprina、铜绿蝇(Lucilia cuprina)、丝光绿蝇(Lucilia sericata)、Lycoria pectoralis、Mansonia titillanus、麦瘿蚊(Mayetiola destructor)、秋家蝇(Musca autumnalis)、家蝇(Musca domestica)、厩腐蝇(Muscina stabulans)、羊狂蝇(Oestrus ovis)、Opomyza florum、欧洲麦秆蝇(Oscinella frit)、天仙子泉蝇(Pegomyahysocyami)、葱蝇(Phorbia antiqua)、萝卜蝇(Phorbia brassicae)、麦地种蝇(Phorbiacoarctata)、银足白蛉(Phlebotomus argentipes)、Psorophora columbiae、胡萝卜茎蝇(Psila rosae)、Psorophora discolor、Prosimulium mixtum、樱桃实蝇(Rhagoletiscerasi)、苹果实蝇(Rhagoletis pomonella)、赤尾麻蝇(Sarcophaga haemorrhoidalis)、肉蝇属(Sarcophaga)、Simulium vittatum、厩螫蝇 (Stomoxys calcitrans)、牛虻(Tabanus bovinus)、Tabanus atratus、红色原虻(Tabanus lineola)和Tabanus similis、Tipula oleracea和欧洲大蚊(Tipula paludosa);
蓟马(缨翅目(Thysanoptera)),例如兰花蓟马(Dichromothrips corbetti)、Dichromothrips ssp.、烟褐蓟马(Frankliniella fusca)、苜蓿花蓟马(Frankliniellaoccidentalis)、东方花蓟马(Frankliniella tritici)、桔梗蓟马(Scirtothrips citri)、稻蓟马(Thrips oryzae)、棕榈蓟马(Thrips palmi)和烟蓟马(Thrips tabaci),
白蚁(等翅目(Isoptera)),例如Calotermes flavicollis、Leucotermesflavipes、金黄异白蚁(Heterotermes aureus)、黄肢散白蚁(Reticulitermes flavipes)、美小黑散白蚁(Reticulitermes virginicus)、欧洲散白蚁(Reticulitermes lucifugus)、桑特散白蚁(Reticulitermes santonensis)、格兰散白蚁(Reticulitermes grassei)、Termes natalensis和台湾乳白蚁(Coptotermes formosanus),
蟑螂(蜚蠊目(Blattaria)-Blattodea),例如德国小蠊(Blattella germanica)、Blattella asahinae、美洲大蠊(Periplaneta americana)、日本大蠊(Periplanetajaponica)、棕色蜚蠊(Periplaneta brunnea)、Periplaneta fuligginosa、澳洲蜚蠊(Periplaneta australasiae)和东方蜚蠊(Blatta orientalis),
臭虫、蚜虫、叶蝉、粉虱、鳞翅昆虫、蝉(半翅目(Hemiptera)),例如拟绿蝽(Acrosternum hilare)、玉米长蝽(Blissus leucopterus)、黑斑烟盲蝽(Cyrtopeltisnotatus)、棉红蝽(Dysdercus cingulatus)、Dysdercus intermedius、麦扁盾蝽(Eurygaster integriceps)、烟草蝽(Euschistus impictiventris)、棉红铃喙缘蝽(Leptoglossus phyllopus)、美洲牧草盲蝽(Lygus lineolaris)、牧草盲蝽(Lyguspratensis)、稻绿蝽(Nezara viridula)、甜菜拟网蝽(Piesma quadrata)、Solubeainsularis、Thyanta perditor、Acyrthosiphon onobrychis、落叶松球蚜(Adelgeslaricis)、Aphidula nasturtii、甜菜蚜(Aphis fabae)、草莓根蚜(Aphis forbesi)、苹果蚜(Aphis pomi)、棉蚜(Aphis gossypii)、北美茶簏子蚜(Aphis grossulariae)、希奈德蚜(Aphis schneideri)、卷叶蚜(Aphis spiraecola)、接骨木蚜(Aphis sambuci)、豌豆蚜(Acyrthosiphon pisum)、茄无网蚜(Aulacorthum solani)、银叶粉虱(Bemisiaargentifolii)、飞廉短尾蚜(Brachycaudus cardui)、李短尾蚜(Brachycaudushelichrysi)、桃短尾蚜(Brachycaudus persicae)、Brachycaudus prunicola、甘蓝蚜(Brevicoryne brassicae)、Capitophorus horni、Cerosipha gossypii、草莓中瘤钉毛蚜(Chaetosiphon fragaefolii)、茶镳隐瘤蚜(Cryptomyzus ribis)、高加索冷杉椎球蚜(Dreyfusia nordmannianae)、云杉椎球蚜(Dreyfusia piceae)、居根西圆尾蚜(Dysaphisradicola)、Dysaulacorthum pseudosolani、车前圆尾蚜(Dysaphis plantaginea)、梨西圆尾蚜(Dysaphis pyri)、蚕豆微叶蝉(Empoasca fabae)、桃大尾蚜(Hyalopterus pruni)、Hyperomyzus lactucae、麦长管蚜(Macrosiphum avenae)、大戟长管蚜(Macrosiphumeuphorbiae)、蔷薇管蚜(Macrosiphon rosae)、巢莱修尾蚜(Megoura viciae)、Melanaphispyrarius、麦无网蚜(Metopolophium dirhodum)、Myzodes persicae、冬葱瘤额蚜(Myzusascalonicus)、Myzus cerasi、李瘤蚜(Myzus varians)、黑茶镳子衲长管蚜(Nasonoviaribis-nigri)、稻飞虱(Nilaparvata lugens)、囊柄瘿绵蚜(Pemphigus bursarius)、蔗飞虱(Perkinsiella saccharicida)、忽布疣蚜(Phorodon humuli)、苹木虱(Psylla mali)、梨木虱(Psylla piri)、冬葱瘤蛾蚜(Rhopalomyzus ascalonicus)、玉米蚜(Rhopalosiphummaidis)、禾谷溢管蚜(Rhopalosiphum padi)、苹草缢管蚜(Rhopalosiphum insertum)、Sappaphis mala、Sappaphis mali、麦二叉蚜(Schizaphis graminum)、Schizoneuralanuginosa、麦长管蚜(Sitobion avenae)、白粉虱(Trialeurodes vaporariorum)、桔二叉蚜(Toxoptera aurantiiand)、葡萄根瘤蚜(Viteus vitifolii)、温带臭虫(Cimexlectularius)、热带臭虫(Cimex hemipterus)、Reduvius senilis、Triatoma属和Ariluscritatus;
蚂蚁、蜜蜂、黄蜂、锯蝇(膜翅目(Hymenoptera)),例如新疆菜叶蜂(Athaliarosae)、切叶蚁(Atta cephalotes)、Atta capiguara、Atta cephalotes、Atta laevigata、Atta robusta、Atta sexdens、Atta texana、举 腹蚁属(Crematogaster)、Hoplocampaminuta、Hoplocampa testudinea、褐毛蚁(Lasius niger)、小黄家蚁(Monomoriumpharaonis)、热带火蚁(Solenopsis geminate)、红火蚁(Solenopsis invicta)、黑火蚁(Solenopsis richteri)、南方火蚁(Solenopsis xyloni)、红蚂蚁(Pogonomyrmexbarbatus)、Pogonomyrmex californicus、Pheidole megacephala、天鹅绒蚂蚁(Dasymutilla occidentalis)、熊蜂属(Bombus)、大黄蜂(Vespula squamosa)、Paravespula vulgaris、Paravespula pennsylvanica、Paravespula germanica、姬胡蜂(Dolichovespula maculata)、黄边胡蜂(Vespa crabro)、胡蜂(Polistes rubiginosa)、Campodontus floridanus和阿根廷蚁(Linepithema humile);
蟋蟀、蚱蜢、蝗虫(直翅目(Orthoptera)),例如居屋艾蟋(Acheta domestica)、蝼蛄(Gryllotalpa gryllotalpa)、飞蝗(Locusta migratoria)、双纹黑蝗(Melanoplusbivittatus)、红足黑蝗(Melanoplus femurrubrum)、墨西哥黑蝗(Melanoplusmexicanus)、迁飞黑蝗(Melanoplus sanguinipes)、石栖黑蝗(Melanoplus spretus)、条纹红蝗(Nomadacris septemfasciata)、美洲沙漠蝗(Schistocerca americana)、沙漠蝗(Schistocerca gregaria)、摩洛哥戟纹蝗(Dociostaurus maroccanus)、庭疾灶螽(Tachycines asynamorus)、塞纳加尔小车蝗(Oedaleus senegalensis)、Zonozerusvariegatus、非洲蔗蝗(Hieroglyphus daganensis)、Kraussaria angulifera、意大利蝗(Calliptamus italicus)、澳洲草栖蝗(Chortoicetes terminifera)和褐色拟飞蝗(Locustana pardalina);
跳蚤(蚤目(Siphonaptera)),例如猫跳蚤(Ctenocephalides felis)、狗跳蚤(Ctenocephalides canis)、印鼠客蚤(Xenopsylla cheopis)、致痒蚤(Pulex irritans)、穿皮潜蚤(Tunga penetrans)和具带病蚤(Nosopsyllus fasciatus),衣鱼、家衣鱼(缨尾目(Thysanura)),例如西洋衣鱼(Lepisma saccharina)和斑衣鱼(Thermobia domestica),
百足虫(唇足纲(Chilopoda)),例如家蚰蜒(Scutigera coleoptrata),
千足虫(倍足纲(Diplopoda)),例如Narceus属,
蠼蛸(革翅目(Dermaptera)),例如欧洲球螋(forficula auricularia),
虱(毛虱目(Phthiraptera)),例如人头虱(Pediculus humanus capitis)、人体虱(Pediculus humanus corporis)、阴虱(Pthirus pubis)、牛血虱(Haematopinuseurysternus)、猪血虱(Haematopinus suis)、牛颚虱(Linognathus vituli)、Bovicolabovis、鸡虱(Menopon gallinae)、Menacanthus stramineus和Solenopotes capillatus;
弹尾目(Collembola(跳虫)),例如棘跳虫属(Onychiurus)
本发明化合物(包括其盐、立体异构体和互变异构体)尤其可用于防治昆虫,优选吮吸或刺吸式昆虫,例如来自缨翅目类、双翅目类和半翅目类的昆虫,尤其是以下属:
缨翅目:烟褐蓟马、苜蓿花蓟马、东方花蓟马、桔梗蓟马、稻蓟马、棕榈蓟马和烟蓟马。
双翅目:例如埃及伊蚊、白纹伊蚊、剌扰伊蚊、墨西哥果蝇、五斑按蚊、Anophelescrucians、白足按蚊、冈比亚按蚊、Anopheles freeborni、海南岛白踝按蚊、云南微小按蚊、四斑按蚊、红头丽蝇、地中海实蝇、蛆症金蝇、Chrysomya hominivorax、Chrysomyamacellaria、鹿蝇、Chrysops silacea、Chrysops atlanticus、螺旋蝇、高粱瘿蚊、嗜人瘤蝇蛆、狂怒库蠓、尖音库蚊、斑蚊、致倦库蚊、媒斑蚊、Culiseta inornata、Culisetamelanura、瓜蝇、油橄榄实蝇、油菜叶瘿蚊、Delia antique、麦地种蝇、灰地种蝇、甘蓝地种蝇、Dermatobia hominis、小毛厕蝇、Geomyza Tripunctata、马蝇、刺舌蝇、须舌蝇、Glossina fuscipes、胶舌蝇、Haematobia irritans、Haplodiplosis equestris、潜蝇属、花生田灰地种蝇、纹皮蝇、Leptoconops torrens、蔬菜斑潜蝇、美国潜叶蝇、Luciliacaprina、铜绿蝇、丝光绿蝇、Lycoria pectoralis、Mansonia titillanus、麦瘿蚊、秋家蝇、家蝇、厩腐蝇、羊狂蝇、Opomyza florum、欧洲麦秆蝇、天仙子泉蝇、葱蝇、萝卜蝇、麦地种蝇、银足白蛉、Psorophora columbiae、胡萝卜茎蝇、Psorophora discolor、Prosimuliummixtum、樱桃实蝇、苹果实蝇、赤尾麻蝇、肉蝇属、Simulium vittatum、厩螫蝇(Stomoxyscalcitrans)、牛虻、Tabanus atratus、红色原虻和Tabanus similis、Tipula oleracea和欧洲大蚊。
半翅目(尤其是蚜虫):Acyrthosiphon onobrychis、落叶松球蚜、Aphidulanasturtii、甜菜蚜、草莓根蚜、苹果蚜、棉蚜、北美茶簏子蚜、希奈德蚜、卷叶蚜、接骨木蚜、豌豆蚜、茄无网蚜、飞廉短尾蚜、李短尾蚜、桃短尾蚜、Brachycaudus prunicola、甘蓝蚜、Capitophorus horni、Cerosipha gossypii、草莓中瘤钉毛蚜、茶镳隐瘤蚜、高加索冷杉椎球蚜、云杉椎球蚜、居根西圆尾蚜、Dysaulacorthum pseudosolani、车前圆尾蚜、梨西圆尾蚜、蚕豆微叶蝉、桃大尾蚜、Hyperomyzus lactucae、麦长管蚜、大戟长管蚜、蔷薇管蚜、巢莱修尾蚜、Melanaphis pyrarius、麦无网蚜、Myzodes persicae、冬葱瘤额蚜、Myzus cerasi、李瘤蚜、黑茶镳子衲长管蚜、稻飞虱、囊柄瘿绵蚜、蔗飞虱、忽布疣蚜、苹木虱、梨木虱、冬葱瘤蛾蚜、玉米蚜、禾谷溢管蚜、苹草缢管蚜、Sappaphis mala、Sappaphis mali、麦二叉蚜、Schizoneura lanuginosa、麦长管蚜、白粉虱、桔二叉蚜和葡萄根瘤蚜。
本发明化合物(包括其盐、立体异构体和互变异构体)尤其可用于防治半翅目和缨翅目昆虫。
本发明进一步提供用于防除无脊椎动物害虫的农业组合物,其包含一定量的至少一种本发明化合物和至少一种具有杀虫作用的惰性液体和/或固体农艺学上可接受的载体,和若需要至少一种表面活性剂。
该组合物可包含单一本发明活性化合物或数种本发明活性化合物的混合物。本发明组合物可包含单独异构体或异构体混合物或盐以及单独互变异构体或互变异构体混合物。
可借助喷雾、雾化、撒粉、撒播或浇灌直接、以其配制剂形式或由其制备的使用形式使用本发明混合物,例如以下列形式使用:可直接喷雾的溶液、粉末、悬浮液或分散体、乳液、油分散体、糊、可撒粉产品、撒播用材料或颗粒。使用形式完全取决于意欲目的;意欲使其确保在每种情况下本发明活性化合物均尽可能最细分布。
配制剂以已知方式制备(关于综述参见(例如)US 3,060,084;EP-A 707445(液体浓缩物);Browning,“Agglomeration”,Chemical Engineering,1967年12月4日,147-48;Perry的Chemical Engineer's Handbook,第 4版,McGraw-Hill,New York,1963,第8页至第57页以及随后各页;WO 91/13546;US 4,172,714;US 4,144,050;US 3,920,442;US 5,180,587;US 5,232,701;US 5,208,030;GB 2,095,558;US 3,299,566;Klingman,WeedControl as a Science,John Wiley and Sons公司,New York,1961;Hance等,WeedControl Handbook,第8版,Blackwell Scientific Publications,Oxford,1989和Mollet,H.,Grubemann,A.,Formulation technology,Wiley VCH Verlag GmbH,Weinheim(Germany),2001,2;D.A.Knowles,Chemistry and Technology of AgrochemicalFormulations,Kluwer Academic Publishers,Dordrecht,1998,例如向活性化合物中掺入适用于农业化学品配制的助剂,例如溶剂和/或载体,若需要乳化剂、表面活性剂和分散剂、防腐剂、消泡剂、防冻剂,对于种子处理配制剂而言,还任选地掺入着色剂和/或粘合剂和/或胶凝剂。
合适的溶剂/载体为(例如):
-溶剂例如水、芳族溶剂(例如Solvesso产物、二甲苯等)、石蜡(例如矿物馏分)、醇(例如甲醇、丁醇、戊醇、苄醇)、酮(例如环己酮、γ-丁内酯)、吡咯烷酮(N-甲基吡咯烷酮(NMP)、N-辛基吡咯烷酮NOP)、乙酸酯(乙二醇二乙酸酯)、乳酸烷基酯、内酯(例如g-丁内酯)、二醇、脂肪酸二甲基酰胺、脂肪酸和脂肪酸酯、甘油三酯、植物或动物来源的油和改性油(例如烷基化植物油)。原则上,还可使用溶剂混合物。
-载体,例如经研磨天然矿物和经研磨合成矿物,例如硅胶、细碎硅酸、硅酸盐、滑石、高岭土、镁质粘土(attaclay)、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙和硫酸镁、氧化镁、经研磨合成材料;肥料,例如,硫酸铵、磷酸铵、硝酸铵、尿素;和植物来源产品,例如谷粉、树皮粉、木粉和坚果壳粉;纤维素粉及其他固体载体。
合适乳化剂为非离子型和阴离子型乳化剂(例如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)。
分散剂的实例为木素亚硫酸盐废液和甲基纤维素。
合适表面活性剂为木素磺酸、萘磺酸、酚磺酸、二丁基萘磺酸、烷基芳基磺酸酯、烷基硫酸酯、烷基磺酸酯、脂肪醇硫酸酯、脂肪酸和硫酸化 脂肪醇二醇醚的碱金属、碱土金属和铵盐,以及磺酸化萘和萘衍生物与甲醛的缩合物、萘或萘磺酸与苯酚和甲醛的缩合物、聚氧化乙烯辛基苯基醚、乙氧基化异辛基酚、辛基酚、壬基酚、烷基苯基聚二醇醚、三丁基苯基聚二醇醚、三硬脂基苯基聚二醇醚、烷基芳基聚醚醇、醇和脂肪醇/氧化乙烯缩合物、乙氧基化蓖麻油、聚氧化乙烯烷基醚、乙氧基化聚氧化丙烯、月桂醇聚乙二醇醚缩醛、山梨醇酯。
还可将防冻剂如甘油、乙二醇、丙二醇和杀菌剂加入配制剂中。
合适消泡剂为(例如)基于硬脂酸硅或硬脂酸镁的消泡剂。
合适防腐剂为(例如)二氯芬和苄醇半缩甲醛。
合适增稠剂为赋予配制剂以假塑性流动行为(即静止时为高粘度且在搅拌阶段为低粘度)的化合物。就此而言,可提及(例如)基于多糖的市售增稠剂,例如Xanthan(来自Kelco的)、23(Rhone Poulenc)或(来自R.T.Vanderbilt)或有机层状硅酸盐,例如 (来自Engelhardt)。适用于本发明分散体的消泡剂为(例如)聚硅氧烷乳液(例如,来自Rhodia的SRE、Wacker或)、长链醇、脂肪酸、有机氟化合物及其混合物。可添加生物杀伤剂以稳定本发明组合物以对抗微生物侵袭。合适生物杀伤剂(例如)基于异噻唑酮,例如由Avecia(或Arch)以商标或由Thor Chemie以RS和由Rohm&Haas以MK出售的化合物。合适防冻剂为有机多醇,例如乙二醇、丙二醇或甘油。这些物质基于活性化合物组合物总量通常以不超过10重量%的量使用。若合适,本发明活性化合物组合物基于所制备的配制剂总量可包含1重量%至5重量%缓冲剂以调节pH,所用缓冲剂的量和类型取决于活性化合物的化学性能。缓冲剂的实例为弱无机或有机酸(例如磷酸、硼酸、乙酸、丙酸、柠檬酸、富马酸、酒石酸、草酸和琥珀酸)的碱金属盐。
适于制备可直接喷雾溶液、乳液、糊或油分散体的物质为具有中至高沸点的矿物油馏分,例如煤油或柴油;此外还有煤焦油和植物或动物来源的油;脂族烃、环烃和芳族烃,例如甲苯、二甲苯、石蜡、四氢化萘、烷基化萘或其衍生物;甲醇、乙醇、丙醇、丁醇、环己醇、环己酮、异佛尔 酮;强极性溶剂,例如二甲亚砜、N-甲基吡咯烷酮和水。
粉剂、撒播用材料和可撒粉产品可通过混合或同时研磨活性物质与固体载体来制备。
可通过使活性化合物与固体载体结合来制备颗粒,例如经涂覆颗粒、经浸渍颗粒和均匀颗粒。固体载体的实例为矿物土,例如硅胶、硅酸盐、滑石、高岭土、镁质粘土、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁,经研磨合成材料;肥料,例如硫酸铵、磷酸铵、硝酸铵、尿素;和植物来源产品,例如谷粉、树皮粗粉、木粉和坚果壳粉;纤维素粉及其他固体载体。
通常,配制剂(即本发明组合物)包含0.01重量%至95重量%,优选0.1重量%至90重量%活性成分。所用活性成分的纯度为90%至100%,优选95%至100%(根据NMR光谱)。
对种子处理而言,可将相应配制剂稀释2至10倍以使即用制剂中活性化合物的以重量计的浓度为0.01-60重量%,优选为0.1-40重量%。
以下为配制剂实例:
1.用水稀释的产品。对种子处理而言,可将经稀释或未经稀释的这些产品施加至种子上。
A)水溶性浓缩物(SL,LS)
将10重量份活性化合物溶于90重量份水或水溶性溶剂中。作为替代方案,可添加润湿剂或其他辅助剂。在用水稀释后,活性化合物溶解,由此获得具有10%(w/w)活性化合物的配制剂。
B)分散性浓缩物(DC)
将20重量份活性化合物溶于70重量份环己酮中,并添加10重量份分散剂(例如聚乙烯基吡咯烷酮)。用水稀释得到分散体,由此获得具有20%(w/w)活性化合物的配制剂。
C)可乳化浓缩物(EC)
将15重量份活性化合物溶于7重量份二甲苯中,并添加十二烷基苯磺酸钙和乙氧基化蓖麻油(在每种情况下均为5重量份)。用水稀释得到乳液,由此获得具有15%(w/w)活性化合物的配制剂。
D)乳液(EW,EO,ES)
将25重量份活性化合物溶于35重量份二甲苯中,并添加十二烷基苯磺酸钙和乙氧基化蓖麻油(在每种情况下均为5重量份)。借助乳化机(例如Ultraturrax)将该混合物引入30重量份水中并将其制成均匀乳液。用水稀释得到乳液,由此获得具有25%(w/w)活性化合物的配制剂。
E)悬浮液(SC,OD,FS)
在搅拌式球磨机中,粉碎20重量份活性化合物,并添加10重量份分散剂、润湿剂和70重量份水或有机溶剂,得到活性化合物细悬浮液。用水稀释,得到活性化合物的稳定悬浮液,由此获得具有20%(w/w)活性化合物的配制剂。
F)水分散性颗粒和水溶性颗粒(WG,SG)
将50重量份活性化合物细研磨,并添加50重量份分散剂和润湿剂并借助机械设备(例如挤出机、喷雾塔、流化床)制成水分散性或水溶性颗粒。用水稀释,得到活性化合物的稳定分散体或溶液,由此获得具有50%(w/w)活性化合物的配制剂。
G)水分散性粉末和水溶性粉末(WP,SP,SS,WS)
在转子-定子磨机中研磨75重量份活性化合物,并添加25重量份分散剂、润湿剂和硅胶。用水稀释,得到活性化合物的稳定分散体或溶液,由此获得具有75%(w/w)活性化合物的配制剂。
H)凝胶配制剂(GF)
在搅拌式球磨机中,将20重量份活性化合物粉碎,并添加10重量份分散剂、1重量份胶凝剂润湿剂和70重量份水或有机溶剂,得到活性化合物细悬浮液。用水稀释,得到活性化合物的稳定悬浮液,由此获得具有20%(w/w)活性化合物的配制剂。
2.对叶面施用而言无需稀释即可施加的产品。对于种子处理目的,可将经稀释或未经稀释的这些产品施加至种子上。
I)可撒粉粉末(DP,DS)
细研磨5重量份活性化合物并与95重量份细碎高岭土充分混合。这得到具有5%(w/w)活性化合物的可撒粉产品。
J)颗粒(GR,FG,GG,MG)
细研磨0.5重量份活性化合物并与95.5重量份载体联合,由此获得具有0.5%(w/w)活性化合物的配制剂。当前方法为挤出、喷雾干燥或流化床。这得到对叶面施用而言不经稀释即可施加的颗粒。
K)ULV溶液(UL)
将10重量份活性化合物溶于90重量份有机溶剂(例如二甲苯)中。这得到具有10%(w/w)活性化合物的产品,其对叶面施用而言不经稀释即可施加。
可通过添加水由乳液浓缩物、糊或可湿性粉剂(可喷雾粉剂、油分散体)来制备水性使用形式。为制备乳液、膏或油分散体,可在水中借助润湿剂、增粘剂、分散剂或乳化剂使这些物质直接或溶于油或溶剂中的形式均化。替换地,可制备包含活性物质、润湿剂、增粘剂、分散剂或乳化剂和(若合适)溶剂或油的浓缩物,且这些浓缩物适于用水稀释。
即用产品中活性成分的浓度可在相对宽范围内变化。通常,这些浓度为0.0001%至10%,优选0.01%至1%。
活性成分还可成功地用于超低容量法(ULV)中,其中可施加包含超过95重量%活性成分的配制剂,或甚至可施加不含添加剂的活性成分。
在本发明的方法和用途中,本发明化合物可与其他活性成分一起使用,例如与其他杀虫剂、杀昆虫剂、除草剂、肥料(例如硝酸铵、尿素、钾碱和过磷酸盐)、植物毒素和植物生长调节剂、安全剂和杀线虫剂一起使用。这些额外成分可依次使用或与上述组合物组合使用,若合适,其还可在紧临使用前添加(桶混物)。例如,可在用其他活性成分处理之前或之后用本发明组合物喷雾植物。
以下列举M为可与本发明化合物一起使用且使用其可产生潜在协调增效效果的杀虫剂,该列表意欲说明可能的组合,但不施加任何限制:
M.1.有机(硫代)磷酸酯化合物:高灭磷(acephate)、唑啶磷(azamethiphos)、乙基谷硫磷(azinphos-ethyl)、谷硫磷(azinphos-methyl)、氯氧磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲硫磷(chlormephos)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、蝇毒磷 (coumaphos)、杀螟腈(cyanophos)、甲基内吸磷(demeton-S-methyl)、二嗪农(diazinon)、敌敌畏(dichlorvos/DDVP)、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、乙拌磷(disulfoton)、EPN、乙硫磷(ethion)、丙线磷(ethoprophos)、伐灭磷(famphur)、苯线磷(fenamiphos)、杀螟松(fenitrothion)、倍硫磷(fenthion)、吡氟硫磷(flupyrazophos)、噻唑硫磷(fosthiazate)、庚烯磷(heptenophos)、异唑磷(isoxathion)、马拉硫磷(malathion)、灭蚜磷(mecarbam)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧乐果(omethoate)、砜吸磷(oxydemeton-methyl)、一六零五(parathion)、甲基对硫磷(parathion-methyl)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、辛硫磷(phoxim)、虫螨磷(pirimiphos-methyl)、丙溴磷(profenofos)、巴胺磷(propetamphos)、丙硫磷(prothiofos)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、喹硫磷(quinalphos)、治螟磷(sulfotep)、丁基嘧啶磷(tebupirimfos)、双硫磷(temephos)、特丁磷(terbufos)、杀虫威(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(trichlorfon)、蚜灭磷(vamidothion);
M.2.氨基甲酸酯化合物:涕灭威(aldicarb)、棉铃威(alanycarb)、虫威(bendiocarb)、丙硫克百威(benfuracarb)、丁酮威(butocarboxim)、丁酮氧威(butoxycarboxim)、甲萘威(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、苯虫威(ethiofencarb)、仲丁威(fenobucarb)、抗螨脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、灭虫威(methiocarb)、灭多虫(methomyl)、速灭威(metolcarb)、甲氨叉威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、久效威(thiofanox)、混杀威(trimethacarb)、XMC、灭杀威(xylylcarb)、唑蚜威(triazamate);
M.3.合成除虫菊酯化合物:氟丙菊酯(acrinathrin)、丙烯除虫菊(allethrin)、右旋丙烯菊酯(d-cis-trans allethrin)、右旋反式丙烯菊酯(d-trans allethrin)、氟氯菊酯(bifenthrin)、生物烯丙菊酯(bioallethrin)、2-环戊烯基生物烯丙菊酯(bioallethrinS-cyclopentenyl)、生物苄呋菊酯(bioresmethrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、高效氟氯氰菊酯(beta-cyfluthrin)、(RS)氯氟氰菊酯(cyhalothrin)、氯氟氰菊酯(lambda-cyhalothrin)、精高效氯氟氰菊酯(gamma-cyhalothrin)、氯氰菊酯(cypermethrin)、甲体氯氰菊酯(alpha-cypermethrin)、乙体氯氰菊酯(beta-cypermethrin)、高效反式氯氰菊酯(theta-cypermethrin)、己体氯氰菊酯(zeta-cypermethrin)、苯醚氰菊酯(cyphenothrin)、溴氰菊酯(deltamethrin)、烯炔菊酯(empenthrin)、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、杀灭菊酯(fenvalerate)、氟氰戊菊酯(flucythrinate)、氟氯苯菊酯(flumethrin)、氟胺氰菊酯(tau-fluvalinate)、溴氟醚菊酯(halfenprox)、咪炔菊酯(imiprothrin)、甲氧苄氟菊酯(metofluthrin)、氯菊酯(permethrin)、苯醚菊酯(phenothrin)、炔酮菊酯(prallethrin)、丙氟菊酯(profluthrin)、除虫菊酯(pyrethrin(除虫菊(pyrethrum)))、灭虫菊(resmethrin)、灭虫硅醚(silafluofen)、七氟菊酯(tefluthrin)、胺菊酯(tetramethrin)、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin);
M.4.保幼激素模拟物:蒙512(hydroprene)、烯虫炔酯(kinoprene)、蒙五一五(methoprene)、双氧威(fenoxycarb)、蚊蝇醚(pyriproxyfen);
M.5.烟酸受体激动剂/拮抗剂化合物:吡虫清(acetamiprid)、杀虫磺(bensultap)、杀螟丹(cartap hydrochloride)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、噻虫嗪(thiamethoxam)、硝胺烯啶(nitenpyram)、烟碱(nicotine)、艾克敌105(spinosad)(别构激动剂)、乙基多杀菌素(spinetoram)(别构激动剂)、噻虫啉(thiacloprid)、杀虫环(thiocyclam)、杀虫双(thiosultap-sodium)和AKD1022;
M.6.GABA门控氯离子通道拮抗剂化合物:氯丹(chlordane)、硫丹(endosulfan)、林丹(gamma-HCH(lindane));乙虫腈(ethiprole)、锐劲特(fipronil)、pyrafluprole,pyriprole;
M.7.氯离子通道活化剂:齐墩螨素(abamectin)、甲氨基阿维菌素苯甲酸 盐(emamectin benzoate)、米尔螨素(milbemectin)、雷皮菌素(lepimectin);
M.8.METI I化合物:喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、嘧螨醚(pyrimidifen)、哒螨酮(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)、嘧虫胺(flufenerim)、鱼藤酮(rotenone);
M.9.METI II和III化合物:灭螨醌(acequinocyl)、fluacyprim、灭蚁腙(hydramethylnon);
M.10.氧化磷酸化去偶剂:氟唑虫清(chlorfenapyr)、二硝酚(DNOC);
M.11.氧化磷酸化抑制剂:三唑锡(azocyclotin)、三环锡(cyhexatin)、杀螨硫隆(diafenthiuron)、杀螨锡(fenbutatin oxide)、克螨特(propargite)、三氯杀螨砜(tetradifon);
M.12.蜕皮干扰剂:灭蝇胺(cyromazine)、环虫酰肼(chromafenozide)、特丁苯酰肼(halofenozide)、甲氧苯酰肼(methoxyfenozide)、双苯酰肼(tebufenozide);
M.13.增效剂:增效醚(piperonyl butoxide)、脱叶膦(tribufos);
M.14.钠通道阻断剂化合物:二唑虫(indoxacarb)、氰氟虫胺(metaflumizone);
M.15.熏蒸剂:溴甲烷(methyl bromide)、氯化苦(chloropicrin)、磺酰氟(sulfuryl fluoride);
M.16.选择性进食阻断剂:冰晶石(cryolite)、拒嗪酮(pymetrozine)、氟啶虫酰胺(flonicamid);
M.17.螨生长抑制剂:四螨嗪(clofentezine)、噻螨酮(hexythiazox)、特苯唑(etoxazole);
M.18.几丁质合成抑制剂:噻嗪酮(buprofezin)、双三氟虫脲(bistrifluron)、定虫隆(chlorfluazuron)、氟脲杀(diflubenzuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氟丙氧脲(lufenuron)、双苯氟脲(novaluron)、多氟虫酰脲(noviflumuron)、伏虫隆(teflubenzuron)、杀虫隆(triflumuron);
M.19.类脂生物合成抑制剂:螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)、螺虫乙酯(spirotetramat);
M.20.章鱼胺能激动剂(octapaminergic agonists):双甲脒(amitraz);
M.21.鱼尼汀(Ryanodine)受体调节剂:氟虫酰胺(flubendiamide)以及邻苯二甲酰胺化合物(R)-、(S)-3-氯-N1-{2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基}-N2-(1-甲基-2-甲基磺酰基乙基)邻苯二甲酰胺(M21.1);
M.22.异唑啉化合物:4-[5-(3,5-二氯苯基)-5-三氟甲基-4,5-二氢异唑-3-基]-2-甲基-N-吡啶-2-基甲基苯甲酰胺(M22.1)、4-[5-(3,5-二氯苯基)-5-三氟甲基-4,5-二氢异唑-3-基]-2-甲基-N-(2,2,2-三氟乙基)苯甲酰胺(M22.2)、4-[5-(3,5-二氯苯基)-5-三氟甲基-4,5-二氢异唑-3-基]-2-甲基-N-[(2,2,2-三氟乙基氨基甲酰基)甲基]苯甲酰胺(M22.3)、4-[5-(3,5-二氯苯基)-5-三氟甲基-4,5-二氢异唑-3-基]萘-1-甲酸[(2,2,2-三氟乙基氨基甲酰基)甲基]酰胺(M22.4)、4-[5-(3,5-二氯苯基)-5-三氟甲基-4,5-二氢异唑-3-基]-N-[(甲氧基亚氨基)甲基]-2-甲基苯甲酰胺(M22.5)、4-[5-(3-氯-5-三氟甲基苯基)-5-三氟甲基-4,5-二氢异唑-3-基]-2-甲基-N-[(2,2,2-三氟乙基氨基甲酰基)甲基]苯甲酰胺(M22.6)、4-[5-(3-氯-5-三氟甲基苯基)-5-三氟甲基-4,5-二氢异唑-3-基]萘-1-甲酸[(2,2,2-三氟乙基氨基甲酰基)甲基]酰胺(M22.7)和5-[5-(3,5-二氯-4-氟苯基)-5-三氟甲基-4,5-二氢异唑-3-基]-2-[1,2,4]三唑-1-基苄腈(M22.8);
M.23.邻氨基苯甲酰胺(Anthranilamide)化合物:氯虫酰胺(chloranthraniliprole)、氰虫酰胺(cyantraniliprole)、5-溴-2-(3-氯吡啶-2-基)-2H-吡唑-3-甲酸[4-氰基-2-(1-环丙基乙基氨基甲酰基)-6-甲基苯基]酰胺(M23.1)、5-溴-2-(3-氯吡啶-2-基)-2H-吡唑-3-甲酸[2-氯-4-氰基-6-(1-环丙基乙基氨基甲酰基)苯基]酰胺(M23.2)、5-溴-2-(3-氯吡啶-2-基)-2H-吡唑-3-甲酸[2-溴-4-氰基-6-(1-环丙基乙基氨基甲酰基)苯基]酰胺(M23.3)、5-溴-2-(3-氯吡啶-2-基)-2H-吡唑-3-甲酸[2-溴-4-氯-6-(1-环丙基乙基氨基甲酰基)苯基]酰胺(M23.4)、5-溴-2-(3-氯吡啶-2-基)-2H-吡唑-3-甲酸[2,4-二氯-6-(1-环丙基乙基氨基甲酰基)苯基]酰胺(M23.5)、5-溴-2-(3-氯吡啶-2-基)-2H-吡唑-3-甲酸[4-氯-2-(1-环丙基乙基氨基甲酰基)-6-甲基苯基]酰胺(M23.6)、N'-(2-{[5-溴-2-(3-氯吡啶-2-基)-2H-吡唑-3-羰基]氨基}-5-氯-3- 甲基苯甲酰基)肼甲酸甲酯(M23.7)、N'-(2-{[5-溴-2-(3-氯吡啶-2-基)-2H-吡唑-3-羰基]氨基}-5-氯-3-甲基苯甲酰基)-N'-甲基肼甲酸甲酯(M23.8)、N'-(2-{[5-溴-2-(3-氯吡啶-2-基)-2H-吡唑-3-羰基]氨基}-5-氯-3-甲基苯甲酰基)-N,N'-二甲基肼甲酸甲酯(M23.9)、N'-(3,5-二溴-2-{[5-溴-2-(3-氯吡啶-2-基)-2H-吡唑-3-羰基]氨基}苯甲酰基)肼甲酸甲酯(M23.10)、N'-(3,5-二溴-2-{[5-溴-2-(3-氯吡啶-2-基)-2H-吡唑-3-羰基]氨基}苯甲酰基)-N'-甲基肼甲酸甲酯(M23.11)和N'-(3,5-二溴-2-{[5-溴-2-(3-氯吡啶-2-基)-2H-吡唑-3-羰基]氨基}苯甲酰基)-N,N'-二甲基肼甲酸甲酯(M23.12);
M.24.丙二腈化合物:2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(3,3,3-三氟丙基)丙二腈(CF2HCF2CF2CF2CH2C(CN)2CH2CH2CF3)(M24.1)和2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(3,3,4,4,4-五氟丁基)丙二腈(CF2HCF2CF2CF2CH2C(CN)2-CH2CH2CF2CF3)(M24.2);
A.25.微生物干扰剂:苏云金芽孢杆菌以色列亚种(Bacillus thuringiensissubsp.Israelensis)、球形芽孢杆菌(Bacillus sphaericus)、苏云金芽胞杆菌鲇泽亚种(Bacillus thuringiensis subsp.Aizawai)、苏云金芽孢杆菌库尔斯塔克亚种(Bacillusthuringiensis subsp.Kurstaki)、苏云金芽胞杆菌粉虫亚种(Bacillus thuringiensissubsp.Tenebrionis);
M.26.氨基呋喃酮化合物:4-{[(6-溴吡啶-3-基)甲基](2-氟乙基)氨基}呋喃-2(5H)-酮(M26.1)、4-{[(6-氟吡啶-3-基)甲基](2,2-二氟乙基)氨基}呋喃-2(5H)-酮(M26.2)、4-{[(2-氯-1,3-噻唑-5-基)甲基](2-氟乙基)氨基}呋喃-2(5H)-酮(M26.3)、4-{[(6-氯吡啶-3-基)甲基](2-氟乙基)氨基}呋喃-2(5H)-酮(M26.4)、4-{[(6-氯吡啶-3-基)甲基](2,2-二氟乙基)氨基}呋喃-2(5H)-酮(M26.5)、4-{[(6-氯-5-氟吡啶-3-基)甲基](甲基)氨基}呋喃-2(5H)-酮(M26.6)、4-{[(5,6-二氯吡啶-3-基)甲基](2-氟乙基)氨基}呋喃-2(5H)-酮(M26.7)、4-{[(6-氯-5-氟吡啶-3-基)甲基](环丙基)氨基}呋喃-2(5H)-酮(M26.8)、4-{[(6-氯吡啶-3-基)甲基](环丙基)氨基}呋喃-2(5H)-酮(M26.9)和4-{[(6-氯吡啶-3-基)甲基](甲基)氨基}呋喃-2(5H)-酮(M26.10);
M.27.各种化合物:磷化铝(aluminium phosphide)、磺胺螨酯(amidoflumet)、benclothiaz、苯螨特(benzoximate)、联苯肼酯(bifenazate)、硼砂、溴螨 酯(bromopropylate)、氰化物、cyenopyrafen、丁氟螨酯(cyflumetofen)、喹菌酮(chinomethionate)、三氯杀螨醇(dicofol)、氟乙酸酯、膦、啶虫丙醚(pyridalyl)、pyrifluquinazon、硫、有机硫化合物、酒石酸氧锑钾(tartar emetic)、sulfoxaflor、N-R'-2,2-二halo-1-R”环丙烷甲酰胺-2-(2,6-二氯-α,α,α-三氟对甲苯基)腙或N-R'-2,2-二(R”')丙酰胺-2-(2,6-二氯-α,α,α-三氟对甲苯基)腙(其中R'为甲基、乙基,halo为氯或溴,R”为氢或甲基且R”'为甲基或乙基)、4-丁-2-炔基氧基-6-(3,5-二甲基哌啶-1-基)-2-氟嘧啶(M27.1)、环丙烷乙酸1,1'-[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-[[(2-环丙基乙酰基)氧基]甲基]-1,3,4,4a,5,6,6a,12,12a,12b-十氢-12-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-3,6-二基]酯(M27.2)和8-(2-环丙基甲氧基-4-三氟甲基苯氧基)-3-(6-三氟甲基哒嗪-3-基)-3-氮杂双环[3.2.1]辛烷(M27.3)。
M组的市售化合物可尤其参见Pesticide Manual,第13版,British CropProtection Council(2003)。
对氧磷(Paraoxon)及其制备已描述于Farm Chemicals Handbook,第88卷,Meister出版公司,2001。吡氟硫磷(Flupyrazofos)已描述于Pesticide Science 54,1988,第237页至第243页和US 4822779中。AKD 1022及其制备已描述于US 6300348中。M21.1由WO2007/101540已知。异唑啉M22.1至M22.8已描述于(例如)WO 2005/085216、WO 2007/079162、WO 2007/026965、WO 2009/126668和WO 2009/051956中。邻氨基苯甲酰胺M23.1至M23.6已描述于WO 2008/72743和WO 200872783中,那些M23.7至M23.12已描述于WO 2007/043677中。丙二腈M24.1和M24.2已描述于WO 02/089579、WO 02/090320、WO 02/090321、WO04/006677、WO 05/068423、WO 05/068432和WO 05/063694中。M26.1至M6.10已描述于(例如)WO 2007/115644中。M27.1描述于(例如)JP 2006131529中。有机硫化合物已描述于WO2007060839中。M27.2已描述于WO 2008/66153和WO 2008/108491中。M27.3已描述于JP2008/115155中。
可结合本发明化合物使用的以下活性物质列举F意欲说明可能的组合但不限于此:
F.I)呼吸抑制剂
a)配合物III在Qo位点的抑制剂(例如嗜球果伞素类)
嗜球果伞素类:腈嘧菌酯(azoxystrobin)、甲香菌酯(coumethoxystrobin)、丁香菌酯(coumoxystrobin)、醚菌胺(dimoxystrobin)、烯肟菌酯(enestroburin)、氟嘧菌酯(fluoxastrobin)、亚胺菌(kresoxim-methyl)、叉氨苯酰胺(metominostrobin)、肟醚菌胺(orysastrobin)、啶氧菌酯(picoxystrobin)、唑菌胺酯(pyraclostrobin)、唑胺菌酯(pyrametostrobin)、唑菌酯(pyraoxystrobin)、pyribencarb、氧啶菌酯(triclopyricarb)/chlorodincarb、肟菌酯(trifloxystrobin)、2-[2-(2,5-二甲基苯氧基甲基)苯基]-3-甲氧基丙烯酸甲酯和2-(2-(3-(2,6-二氯苯基)-1-甲基亚烯丙基氨基氧甲基)苯基)-2-甲氧亚氨基-N-甲基乙酰胺;
唑烷二酮类和咪唑啉酮类:唑酮菌(famoxadone)、咪唑菌酮(fenamidone);
F.I-2)配合物II的抑制剂(例如羧酰胺):
羧酰苯胺类:麦锈灵(benodanil)、bixafen、啶酰菌胺(boscalid)、萎锈灵(carboxin)、呋菌胺(fenfuram)、环酰菌胺(fenhexamid)、氟吡菌酰胺(fluopyram)、氟酰胺(flutolanil)、呋吡唑灵(furametpyr)、isopyrazam、异噻菌胺(isotianil)、丙氧灭绣胺(mepronil)、氧化萎锈灵(oxycarboxin)、penflufen、吡噻菌胺(penthiopyrad)、sedaxane、叶枯酞(tecloftalam)、溴氟唑菌(thifluzamide)、噻酰菌胺(tiadinil)、2-氨基-4-甲基噻唑-5-甲酰苯胺、N-(3',4',5'-三氟联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺、N-(4'-三氟甲硫基联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺和N-(2-(1,3,3-三甲基丁基)苯基)-1,3-二甲基-5-氟-1H-吡唑-4-甲酰胺;
F.I-3)配合物III在Qi位点的抑制剂:氰霜唑(cyazofamid)、amisulbrom;
F.I-4)其他呼吸抑制剂(配合物I,去偶剂)
二氟林(diflumetorim)、四氯硝基苯(tecnazen)、嘧菌腙(ferimzone)、ametoctradin、硅噻菌胺(silthiofam);
硝基苯基衍生物:乐杀螨(binapacryl)、敌螨通(dinobuton)、敌螨普(dinocap)、氟啶胺(fluazinam)、异丙消(nitrthal-isopropyl);
有机金属化合物:三苯锡基盐,例如薯瘟锡(fentin-acetate)、三苯锡氯(fentinchloride)或毒菌锡(fentin hydroxide);
F.II)甾醇生物合成抑制剂(SBI杀真菌剂)
F.II-1)C14去甲基酶抑制剂(DMI杀真菌剂,例如三唑类、咪唑类)
三唑类:戊环唑(azaconazole)、双苯三唑醇(bitertanol)、糠菌唑(bromuconazole)、环唑醇(cyproconazole)、醚唑(difenoconazole)、烯唑醇(diniconazole)、烯唑醇M(diniconazole-M)、氧唑菌(epoxiconazole)、腈苯唑(fenbuconazole)、喹唑菌酮(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、己唑醇(hexaconazole)、酰胺唑(imibenconazole)、环戊唑醇(ipconazole)、环戊唑菌(metconazole)、腈菌唑(myclobutanil)、多效唑(paclobutrazole)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙硫菌唑(prothioconazole)、硅氟唑(simeconazole)、戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、三唑酮(triadimefon)、唑菌醇(triadimenol)、戊叉唑菌(triticonazole)、烯效唑(uniconazole);
咪唑类:抑霉唑(imazalil)、稻瘟酯(pefurazoate)、oxpoconazole、丙氯灵(prochloraz)、氟菌唑(triflumizole);
嘧啶类、吡啶类和哌嗪类:异嘧菌醇(fenarimol)、氟苯嘧啶醇(nuarimol)、啶斑肟(pyrifenox)、嗪氨灵(triforine);
F.II-2)δ14-还原酶抑制剂(胺类,例如吗啉类、哌啶类)
吗啉类:4-十二烷基-2,6-二甲基吗啉(aldimorph)、吗菌灵(dodemorph)、吗菌灵乙酸酯(dodemorph-acetate)、丁苯吗啉(fenpropimorph)、克啉菌(tridemorph);
哌啶类:苯锈啶(fenpropidin)、粉病灵(piperalin);
螺环菌胺类:螺茂胺(spiroxamine);
F.II-3)3-酮基还原酶抑制剂:羟基酰替苯胺类:环酰菌胺(fenhexamid);
F.III)核酸合成抑制剂
F.III-1)RNA、DNA合成
苯基酰胺或酰基氨基酸杀真菌剂:苯霜灵(benalaxyl)、精苯霜灵(benalaxyl-M)、kiralaxyl、甲霜灵(metalaxyl)、精甲霜灵(metalaxyl-M) (mefenoxam)、甲呋酰胺(ofurace)、霜灵(oxadixyl);
异唑类和异噻唑啉酮类:土菌消(hymexazole)、异噻菌酮(octhilinone);
F.III-2)DNA拓扑异构酶抑制剂:恶喹酸(oxolinic acid);
F.III-3)核苷酸代谢酶(例如腺苷酸去胺酶)
羟基(2-氨基)嘧啶类:磺嘧菌灵(bupirimate);
F.IV)细胞分裂和/或细胞骨架抑制剂
F.IV-1)Tubulin抑制剂:苯并咪唑类和托布津类(thiophanate):苯菌灵(benomyl)、多菌灵(carbendazim)、麦穗宁(fuberidazole)、涕必灵(thiabendazole)、甲基托布津(thiophanate methyl);
三唑并嘧啶类:5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5a]嘧啶;
F.IV-2)其他细胞分裂抑制剂
苯甲酰胺类和苯基乙酰胺类:乙霉威(diethofencarb)、噻唑菌胺(ethaboxam)、戊菌隆(pencycuron)、氟吡菌胺(fluopicolide)、苯酰菌胺(zoxamide);
F.IV-3)肌动蛋白抑制剂:二苯甲酮类:苯菌酮(metrafenone);
F.V)氨基酸和蛋白合成抑制剂
F.V-1)蛋氨酸合成抑制剂(苯胺基嘧啶类)
苯胺基嘧啶类:环丙嘧啶(cyprodinil)、嘧菌胺(mepanipyrim)、氯草定(nitrapyrin)、二甲嘧菌胺(pyrimethanil);
F.V-2)蛋白合成抑制剂(苯胺基嘧啶类)
抗生素类:灭瘟素(blasticidin-S)、春雷素(kasugamycin)、水合春雷素(kasugamycin hydrochloride hydrate)、米多霉素(mildiomycin)、链霉素(streptomycin)、土霉素(oxytetracyclin)、多氧霉素(polyoxine)、井冈霉素(validamycin A);
F.VI)信号传导抑制剂
F.VI-1)MAP/组胺酸激酶抑制剂(例如苯胺基嘧啶类)
二羧酰亚胺类:氟菌安(fluoroimide)、异丙定(iprodione)、杀菌利(procymidone)、烯菌酮(vinclozolin);
苯基吡咯类:拌种咯(fenpiclonil)、氟菌(fludioxonil);
F.VI-2)G蛋白抑制剂:喹啉类:喹氧灵(quinoxyfen);
F.VII)类脂和膜合成抑制剂;
F.VII-1)磷脂生物合成抑制剂:
有机磷化合物:克瘟散(edifenphos)、异稻瘟净(iprobenfos)、定菌磷(pyrazophos);
二硫杂戊环类:稻瘟灵(isoprothiolane);
F.VII-2)类脂过氧化:
芳族烃类:氯硝胺(dicloran)、五氯硝基苯(quintozene)、四氯硝基苯(tecnazene)、甲基立枯磷(tolclofos-methyl)、联苯、地茂散(chloroneb)、氯唑灵(etridiazole);
F.VII-3)羧酸酰胺类(CAA杀真菌剂)
肉桂酸或扁桃酸酰胺:烯酰吗啉(dimethomorph)、氟吗啉(flumorph)、双炔酰菌胺(mandiproamid)、丁吡吗啉(pyrimorph);
缬氨酰胺氨基甲酸酯:苯噻菌胺(benthiavalicarb)、异丙菌胺(iprovalicarb)、pyribencarb、valifenalate和N-(1-(1-(4-氰基苯基)乙磺酰基)丁-2-基)氨基甲酸(4-氟苯基)酯;
F.VII-4)影响细胞膜渗透性的化合物和脂肪酸
氨基甲酸酯:百维灵(propamocarb)、霜霉威盐酸盐(propamocarb-hydrochlorid);
F.VIII)具有多位点作用的抑制剂
F.VIII-1)无机活性物质:波尔多液(Bordeaux混合物),醋酸铜,氢氧化铜,王铜(copper oxychloride),碱式硫酸铜,硫;
F.VIII-2)硫代-和二硫代氨基甲酸盐:福美铁(ferbam)、代森锰锌(mancozeb)、代森锰(maneb)、威百亩(metam)、磺菌威(methasulphocarb)、代森联(metiram)、甲基代森锌(propineb)、福美双(thiram)、代森锌(zineb)、福美锌(ziram);
F.VIII-3)有机氯化合物(例如邻苯二甲酰亚胺类、磺酰胺类、氯代腈类):敌菌灵(anilazine)、百菌清(chlorothalonil)、敌菌丹(captafol)、克菌丹 (captan)、灭菌丹(folpet)、抑菌灵(dichlofluanid)、双氯酚(dichlorophen)、磺菌胺(flusulfamide)、六氯苯(hexachlorobenzene)、五氯酚(pentachlorphenole)及其盐、四氯苯酞(phthalide)、对甲抑菌灵(tolylfluanid)、N-(4-氯-2-硝基苯基)-N-乙基-4-甲基苯磺酰胺;
F.VIII-4)胍类:胍、多果定(dodine)、多果定游离碱、双胍盐(guazatine)、双胍辛胺(guazatine-acetate)、双胍辛醋酸盐(iminoctadine)、双胍辛胺三乙酸盐(iminoctadine-triacetate)、双八胍盐(iminoctadine tris(albesilate));
F.VIII-5)蒽醌类:二噻农(dithianon);
F.IX)细胞壁合成抑制剂
F.IX-1)葡聚糖合成抑制剂:井冈霉素(validamycin)、多氧霉素(polyoxin B);
F.IX-2)黑色素合成抑制剂:咯喹酮(pyroquilon)、三环唑(tricyclazole)、氯环丙酰胺(carpropamide)、双氯氰菌胺(dicyclomet)、氰菌胺(fenoxanil);
F.X)植物防御诱导剂
F.X-1)水杨酸路径:噻二唑素(acibenzolar-S-methyl);
F.X-2)其他:噻菌灵(probenazole)、异噻菌胺(isotianil)、噻酰菌胺(tiadinil)、调环酸钙(prohexadione-calcium);
膦酸酯类:藻菌磷(fosetyl)、乙磷铝(fosetyl-aluminum)、亚磷酸及其盐;
F.XI)未知作用模式:拌棉醇(bronopol)、灭螨蜢(chinomethionat)、环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、棉隆(dazomet)、咪菌威(debacarb)、哒菌清(diclomezine)、野燕枯(difenzoquat)、野燕枯甲基硫酸酯(difenzoquat-methylsulfate)、二苯基胺、氟联苯菌(flumetover)、磺菌胺(flusulfamide)、flutianil、磺菌威(methasulfocarb)、喹啉铜(oxin-copper)、丙氧喹啉(proquinazid)、tebufloquin、叶枯酞(tecloftalam)、唑菌嗪(triazoxide)、2-丁氧基-6-碘-3-丙基苯并吡喃-4-酮、N-(环丙基甲氧亚氨基-(6-二氟甲氧基-2,3-二氟苯基)甲基)-2-苯基乙酰胺、N'-(4-(4-氯-3-三氟甲基苯氧基)-2,5-二甲基苯基)-N-乙基-N-甲基甲脒、N'-(4-(4-氟-3-三氟甲基-苯氧基)-2,5-二甲基苯基)-N-乙基-N-甲基甲脒、N'-(2-甲基-5- 三氟甲基-4-(3-三甲基甲硅烷基丙氧基)苯基)-N-乙基-N-甲基甲脒、N'-(5-二氟甲基-2-甲基-4-(3-三甲基甲硅烷基丙氧基)苯基)-N-乙基-N-甲基甲脒、2-{1-[2-(5-甲基-3-三氟甲基吡唑-1-基)乙酰基]哌啶-4-基}噻唑-4-甲酸甲基-(1,2,3,4-四氢萘-1-基)酰胺、2-{1-[2-(5-甲基-3-三氟甲基吡唑-1-基)乙酰基]哌啶-4-基}噻唑-4-甲酸甲基-(R)-1,2,3,4-四氢萘-1-基酰胺、甲氧基乙酸6-叔丁基-8-氟-2,3-二甲基喹啉-4-基酯和N-甲基-2-{1-[(5-甲基-3-三氟甲基-1H-吡唑-1-基)乙酰基]哌啶-4-基}-N-[(1R)-1,2,3,4-四氢萘-1-基]-4噻唑甲酰胺、3-[5-(4-氯苯基)-2,3-二甲基异唑烷-3-基]吡啶、啶菌恶唑(pyrisoxazole)、5-氨基-2-异丙基-3-氧代-4-邻甲苯基-2,3-二氢吡唑-1-硫代甲酸S-烯丙基酯、N-(6-甲氧基吡啶-3-基)环丙烷甲酰胺、5-氯-1-(4,6-二甲氧基嘧啶-2-基)-2-甲基-1H-苯并咪唑、2-(4-氯苯基)-N-[4-(3,4二甲氧基苯基)异唑-5-基]-2-丙-2-炔氧基乙酰胺;
F.XI)生长调节剂:
脱落酸(abscisic acid)、先甲草胺(amidochlor)、嘧啶醇(ancymidol)、苄胺基嘌呤(6-benzylaminopurine)、油菜素内酯(brassinolide)、地乐胺(butralin)、矮壮素阳离子(chlormequat)(矮壮素(chlormequat chloride))、氯化胆碱(choline chloride)、环丙酸酰胺(cyclanilide)、丁酰肼(daminozide)、敌草克(dikegulac)、噻节因(dimethipin)、2,6-二甲基吡啶(2,6-dimethylpuridine)、乙烯利(ethephon)、抑芽敏(flumetralin)、呋嘧醇(flurprimidol)、达草氟(fluthiacet)、调吡脲(forchlorfenuron)、九二O(gibberellic acid)、抗倒胺(inabenfide)、吲哚-3-乙酸、抑芽丹(maleichydrazide)、氟草磺(mefluidide)、助壮素阳离子(mepiquat)(助壮素(mepiquat chloride))、萘乙酸、N-6-苄基腺嘌呤、多效唑、调环酸(prohexadione)(调环酸钙)、茉莉酸丙酯(prohydrojasmon)、赛二唑素(thidiazuron)、抑芽唑(triapenthenol)、脱叶磷(tributylphosphorotrithioate)、2,3,5-三碘苯甲酸、抗倒酯(trinexapac-ethyl)和烯效唑;
F.XII)生物控制剂
抗真菌生物控制剂:NRRL号为B-21661的枯草芽孢杆菌(Bacillus substilis)菌株(例如来自AgraQuest,Inc.,USA.的 MAX和ASO),NRRL号为B-30087的短小芽孢杆菌(Bacillus pumilus)菌株(例如来自AgraQuest,Inc.,USA的 和Plus),奥德曼细基格孢(Ulocladium oudemansii)(例如来自新西兰BotriZen Ltd.的产品BOTRY-ZEN),脱乙酰壳多糖(例如来自新西兰BotriZen Ltd.的ARMOUR-ZEN)。
可通过本领域已知的任何施加方法使无脊椎动物害虫(还称作“动物害虫”,即昆虫、蜘蛛和线虫)、植物、其中植物生长或可能生长的土壤或水与本发明化合物或包含其的组合物接触。因此,“接触”包括直接接触(将化合物/组合物直接施加至无脊椎动物害虫或植物上-通常施加至植物的叶片、茎或根)和间接接触(将化合物/组合物施加至无脊椎动物害虫或植物的场所)。
本发明化合物或包含其的杀虫组合物可用于通过使植物/作物与杀虫有效量的本发明化合物接触来保护生长中的植物和作物以防动物害虫(尤其是昆虫、螨虫或蜘蛛)侵袭或侵染。术语“作物”是指生长中的作物和已收获的作物。
本发明化合物和包含它们的组合物在各种栽培植物上防除大量昆虫特别重要,所述植物如禾谷类、根系作物、油料作物、蔬菜、香料作物、观赏植物,例如硬粒小麦和其他小麦、大麦、燕麦、黑麦、玉米(饲料玉米和糖用玉米/甜玉米和饲料玉米)、大豆、油料作物、十字花科、棉花、向日葵、香蕉、稻、油籽油菜、芜菁油菜、糖用甜菜、饲料甜菜、茄子、土豆、禾草、草坪、草皮、饲料禾草、西红柿、韭葱、南瓜、卷心菜、刺茎莴苣、胡椒、黄瓜、甜瓜、芸苔属(Brassica)、甜瓜、菜豆、豌豆、大蒜、洋葱、胡萝卜、块茎植物如土豆、甘蔗、烟草、葡萄、矮牵牛、天竺葵/香叶天竺葵、三色堇和凤仙花的种子。
本发明化合物通过用杀虫有效量的活性化合物处理昆虫或要防止昆虫侵袭的植物、植物繁殖材料如种子、土壤、表面、材料或空间而直接或以组合物形式使用。施用可以在植物、植物繁殖材料如种子、土壤、表面、材料或空间被昆虫侵染之前和之后进行。
此外,可通过使杀虫有效量的本发明化合物与目标害虫、其食物供应源、栖息地、繁殖地或其场所接触来防治无脊椎动物害虫。因此,可在场所、生长中的作物或已收获作物被害虫侵染之前或之后进行施加。
还可预防性地将本发明化合物施加至预期害虫会出现的位置。
本发明化合物还可用于保护生长中的植物以防害虫侵袭或侵染,其通过使该植物与杀虫有效量的本发明化合物接触来实施。因此,“接触”包括直接接触(将化合物/组合物直接施加至害虫和/或植物上-通常施加至植物叶片、茎或根)和间接接触(将化合物/组合物施加至害虫和/或植物场所)。
“场所”意指其中害虫或寄生虫生长或可能生长的栖息地、繁殖地、植物、种子、土壤、区域、材料或环境。
通常而言,“杀虫有效量”是指对生长获得可观察到的效果所需的活性成分的量,所述效果包括坏死、死亡、阻滞、预防和去除效果,破坏效果或减少目标生物体的出现和活动的效果。对于在本发明中使用的各种化合物/组合物,杀虫有效量可以变化。组合物的杀虫有效量也会根据主要条件如所需杀虫效果及持续时间、天气、目标物种、场所、施用方式等而变化。
在土壤处理或施用于害虫居住地或巢穴的情况下,活性成分量为0.0001-500g/100m2,优选0.001-20g/100m2。
在材料保护中的常规施用率例如为0.01-1000g活性化合物/m2被处理材料,理想的是0.1-50g/m2。
用于材料浸渍中的杀昆虫组合物通常含有0.001-95重量%,优选0.1-45重量%,更优选1-25重量%至少一种驱避剂和/或杀昆虫剂。
为了用于处理农作物,本发明活性成分的施用率可以为0.1-4000g/ha,理想的是25-600g/ha,更理想的是50-500g/ha。
本发明化合物通过接触(经由土壤、玻璃、墙壁、床网、地毯、植物部分或动物部分)和摄取(诱饵或植物部分)而有效。
还可以施用本发明化合物以对抗非作物昆虫害虫如蚂蚁、白蚁、黄蜂、蝇、蚊子、蟋蟀或蟑螂。为了用于对抗所述非作物害虫,优选将本发明化合物用于诱饵组合物中。
诱饵可以是液体、固体或半固体制剂(例如凝胶)。固体诱饵可以制成各 种适合相应应用的形状和形式,如颗粒、块、棒、片。液体诱饵可以填充到各种装置中以确保适当施用,例如敞开容器、喷雾装置、液滴供应源或蒸发源。凝胶可以基于含水基质或油性基质且可以按照粘性、水分保留或老化特性根据特定要求配制。
用于组合物中的诱饵是具有足够的吸引力以刺激诸如蚂蚁、白蚁、黄蜂、蝇、蚊子、蟋蟀等的昆虫或蟑螂食用它的产品。吸引力可以通过使用进食刺激剂或性信息素调控。食物刺激剂例如并不穷举地选自动物和/或植物蛋白质(肉-、鱼-或血液膳食,昆虫部分、蛋黄)、动物和/或植物来源的脂肪和油或单-、低聚-或聚有机糖类,尤其是蔗糖、乳糖、果糖、右旋糖、葡萄糖、淀粉、果胶或甚至糖蜜或蜂蜜。水果、作物、植物、动物、昆虫的新鲜或腐败部分或其特定部分也可以用作进食刺激剂。已知性信息素更具昆虫特异性。特殊信息素描述于文献中并且对本领域熟练技术人员是已知的。
为了用于诱饵组合物中,活性成分的典型含量为0.001-15重量%,理想的是0.001-5%重量%活性成分。
本发明化合物的配制剂如气雾剂(例如在喷雾罐中)、油喷雾剂或泵喷雾剂高度适于非专业使用者来防治害虫如蝇、跳蚤、蜱、蚊子或蟑螂。气雾剂配方优选由如下组分构成:活性化合物;溶剂如低级醇(例如甲醇、乙醇、丙醇、丁醇),酮类(例如丙酮、甲基乙基酮),沸程为约50-250℃的链烷烃(例如煤油),二甲基甲酰胺,N-甲基吡咯烷酮,二甲亚砜,芳族烃类如甲苯、二甲苯,水;此外还有助剂,例如乳化剂如山梨糖醇单油酸酯、具有3-7mol氧化乙烯的油基乙氧基化物、脂肪醇乙氧基化物,芳香油如精油,中等脂肪酸与低级醇的酯,芳族羰基化合物;合适的话还有稳定剂如苯甲酸钠,两性表面活性剂,低级环氧化物,原甲酸三乙酯和需要的话推进剂如丙烷、丁烷、氮气、压缩空气、二甲醚、二氧化碳、氧化亚氮或这些气体的混合物。
油喷雾配制剂与气雾剂配方的不同在于没有使用推进剂。
为了用于喷雾组合物中,活性成分的含量为0.001-80重量%,优选0.01-50重量%,最优选0.01-15重量%。
本发明化合物及其相应的组合物还可以用于蚊香片和熏蒸片,发烟盒、蒸发器板或长效蒸发器以及扑蛾纸、扑蛾垫或其他与热无关的蒸发器体系 中。
用本发明化合物及其相应组合物控制由昆虫传递的传染性疾病(例如疟疾、登革热和黄热病,淋巴丝虫病以及利什曼病)的方法也包括处理棚屋和房子的表面、空气喷雾和浸渍窗帘、帐篷、衣物、床品、采采蝇网等。施用于纤维、织物、编织物、无纺织物、网状材料或箔以及篷布上的杀虫组合物优选包含包括杀虫剂、任选的驱除剂和至少一种粘合剂的混合物。合适的驱除剂例如为N,N-二乙基-间甲苯甲酰胺(DEET),N,N-二乙基苯基乙酰胺(DEPA),1-(3-环己烷-1-基羰基)-2-甲基哌啶,(2-羟基甲基环己基)乙酸内酯,2-乙基-1,3-己二醇,避虫酮,甲基新癸酰胺(MNDA),不用于昆虫防治的拟除虫菊酯如{(+/-)-3-烯丙基-2-甲基-4-氧代环戊-2-(+)-烯基-(+)-反式-菊酸酯(Esbiothrin),衍生于植物提取物或与植物提取物相同的驱除剂如1,8-萜二烯、丁子香酚、(+)-Eucamalol(1)、(-)-1-表-eucamalol,或来自诸如花皮桉(Eucalyptus maculata)、蔓荆(Vitex rotundifolia)、Cymbopogan martinii、香茅(Cymbopogan citratus)(柠檬草)、亚香茅(Cymopogannartdus(香茅))的植物的粗植物提取物。合适的粘合剂例如选自如下单体的聚合物和共聚物:脂族酸的乙烯基酯(如乙酸乙烯酯和支链烷烃羧酸乙烯基酯),醇的丙烯酸酯和甲基丙烯酸酯,如丙烯酸丁酯、丙烯酸2-乙基己基酯和丙烯酸甲酯,单烯属和二烯属不饱和烃,如苯乙烯,以及脂族二烯烃,如丁二烯。
窗帘和床品的浸渍通常通过将纺织材料浸入杀虫剂的乳液或分散体中或将它们喷雾于床品上而进行。
本发明化合物及其组合物可以用于保护木质材料如树木、护栏、枕木等,以及建筑物如房子、附属建筑、工厂,还有建筑材料、家具、皮革、纤维、乙烯基制品、电线和电缆等以防蚂蚁和/或白蚁,并防止蚂蚁和白蚁损害作物或人类(例如当害虫侵入房子和公共设施时)。本发明化合物不仅施用于周围的土壤表面或地板下的土壤中以保护木质材料,而且还可以施用于堆积制品如地板下混凝土、亭柱、梁、胶合板、家具等的表面,木质制品如碎料板、半包板(half board)等以及乙烯基制品如包覆的电线、乙烯基片材,绝热材料如苯乙烯泡沫等。在防止蚂蚁损害作物或人类的施用中,将本发明的蚂蚁 防治剂施用于作物或周围土壤,或直接施用于蚂蚁的巢穴等。
因此本发明化合物适用于处理植物繁殖材料,尤其是种子以保护其以防昆虫害虫,尤其是土壤昆虫害虫以及保护所得植物的根和芽以防土壤害虫和叶面昆虫。
本发明化合物尤其可以用于保护种子以防土壤害虫并保护所得植物的根和芽以防土壤害虫和叶面昆虫。优选保护所得植物的根和芽。更优选保护所得植物的芽以防刺吸式昆虫,其中最优选保护以防蚜虫。
因此,本发明包括一种保护种子以防昆虫,尤其是土壤昆虫以及保护秧苗的根和芽以防昆虫,尤其是土壤和叶面昆虫的方法,所述方法包括在播种之前和/或在预萌发之后使种子与本发明化合物,包括其盐接触。特别优选一种其中保护植物的根和芽的方法,更优选一种其中保护植物芽以防刺吸式昆虫的方法,最优选一种其中保护植物芽以防蚜虫的方法。
术语种子包括所有种类的种子和植物繁殖体,包括但不限于真正的种子、种子切片(seed piece)、吸枝、球茎、鳞茎、果实、块茎、谷粒、插条、伐条(cut shoot)等,并且在优选实施方案中指真正的种子。
术语种子处理包括所有本领域已知的合适种子处理技术,如拌种、种子涂敷、种子撒粉、种子浸泡和种子压丸。
本发明还包括涂有或含有活性化合物的种子。
术语“涂有和/或含有”通常是指活性成分在施用时绝大部分处于繁殖产品的表面上,但更大或更小部分的成分可能渗入繁殖产品中,这取决于施用方法。当(再)种植所述繁殖产品时,它可能吸收活性成分。
合适的种子为禾谷类、根系作物、油料作物、蔬菜、香料作物、观赏植物的种子,例如硬粒小麦和其他小麦、大麦、燕麦、黑麦、玉米(饲料玉米和糖用玉米/甜玉米和饲料玉米)、大豆、油料作物、十字花科、棉花、向日葵、香蕉、稻、油籽油菜、芜菁油菜、糖用甜菜、饲料甜菜、茄子、土豆、禾草、草坪、草皮、饲料禾草、西红柿、韭葱、南瓜、卷心菜、刺茎莴苣、胡椒、黄瓜、甜瓜、芸苔属(Brassica)、甜瓜、菜豆、豌豆、大蒜、洋葱、胡萝卜、块茎植物如土豆、甘蔗、烟草、葡萄、矮牵牛、天竺葵/香叶天竺葵、三色堇和凤仙花。
此外,活性化合物还可以用于处理由于包括基因工程方法在内的育种而耐受除草剂或杀真菌剂或杀虫剂作用的植物的种子。
例如,活性化合物可以用于处理耐受选自磺酰脲类、咪唑啉酮类、草铵膦(glufosinate-ammonium)或草甘膦异丙胺盐(glyphosate-isopropylammonium)和类似活性物质的除草剂的植物(例如参见EP-A 242236,EP-A 242 246、WO 92/00377、EP-A 257993,US 5,013,659)或转基因农作物如棉花的种子,后者能够产生苏云金芽孢杆菌毒素(Bt毒素)以使植物耐受某些害虫(EP-A 142 924,EP-A 193 259)。
此外,活性化合物还可以用于处理与现有植物相比具有修饰特性的植物的种子,它们例如可能通过传统育种方法和/或突变体产生或通过重组程序而产生。例如,已经描述了许多为修饰植物中合成的淀粉而重组修饰农作物的情形(例如WO 92/11376,WO 92/14827,WO 91/19806),或具有修饰的脂肪酸组成的转基因植物(WO 91/13972)。
活性化合物的种子处理施用通过在播种植物之前和植物出苗之前对种子喷雾或撒粉而进行。
尤其可用于种子处理的组合物例如为:
A可溶性浓缩物(SL、LS)
D乳液(EW、EO、ES)
E悬浮液(SC、OD、FS)
F水分散性颗粒和水溶性颗粒(WG、SG)
G水分散性粉末和水溶性粉末(WP、SP、WS)
H凝胶配制剂(GF)
I可撒粉粉末(DP、DS)
常规种子处理配制剂例如包括可流动浓缩物FS、溶液LS、干处理粉末DS、淤浆处理用水分散性粉末WS、水溶性粉末SS、乳液ES和EC以及凝胶配制剂GF。这些配制剂可以经稀释或不经稀释而施用于种子上。对种子的施用在播种之前进行,直接施用于种子上或在种子已经预萌发之后施用。
在优选实施方案中,将FS配制剂用于种子处理。FS配制剂通常可包 含1-800g/l活性成分,1-200g/l表面活性剂,0-200g/l防冻剂,0-400g/l粘合剂,0-200g/l颜料和至多1升溶剂,优选水。
用于种子处理的本发明化合物的尤其优选FS配制剂通常包含0.1-80重量%(1-800g/l)活性成分,0.1-20重量%(1-200g/l)至少一种表面活性剂,例如0.05-5重量%润湿剂和0.5-15重量%分散剂,至多20重量%,例如5-20%防冻剂,0-15重量%,例如1-15重量%颜料和/或染料,0-40重量%,例如1-40重量%粘合剂(粘结剂/粘附剂),任选至多5重量%,例如0.1-5重量%增稠剂,任选0.1-2%消泡剂和任选防腐剂如生物杀伤剂、抗氧化剂等,例如其量为0.01-1重量%,以及达到100重量%的填料/载体。
种子处理配制剂还可额外包含粘合剂和任选包含着色剂。
可以加入粘合剂以改进处理之后活性物质在种子上的粘附。合适的粘合剂是氧化烯如氧化乙烯或氧化丙烯的均聚物和共聚物,聚乙酸乙烯酯,聚乙烯醇,聚乙烯基吡咯烷酮及其共聚物,乙烯-乙酸乙烯酯共聚物,丙烯酸系均聚物和共聚物,聚乙烯胺,聚乙烯酰胺和聚乙烯亚胺,多糖如纤维素、纤基乙酸钠和淀粉,聚烯烃均聚物和共聚物如烯烃/马来酸酐共聚物,聚氨酯,聚酯,聚苯乙烯均聚物和共聚物。
任选还可以在配制剂中包括着色剂。对种子处理配制剂合适的着色剂或染料是若丹明B、C.I.颜料红112、C.I.溶剂红1、颜料蓝15:4、颜料蓝15:3、颜料蓝15:2、颜料蓝15:1、颜料蓝80、颜料黄1、颜料黄13、颜料红112、颜料红48:2、颜料红48:1、颜料红57:1、颜料红53:1、颜料橙43、颜料橙34、颜料橙5、颜料绿36、颜料绿7、颜料白6、颜料棕25、碱性紫10、碱性紫49、酸性红51、酸性红52、酸性红14、酸性蓝9、酸性黄23、碱性红10、碱性红108。
胶凝剂的实例是角叉菜
在种子处理中,本发明化合物的施用率通常为0.1g-10kg/100kg种子,优选1g-5kg/100kg种子,更优选1-1000g/100kg种子,尤其是1-200g/100kg种子。
因此,本发明还涉及包含如本文所定义的本发明化合物,包括其在农业上可使用的盐的种子。本发明化合物,包括其在农业上可使用的盐的量通常 在0.1g-10kg/100kg种子,优选1g-5kg/100kg种子,尤其是1-1000g/100kg种子内变化。对于特殊作物如莴苣,施用率可能更高。
原则上,可用于处理种子的方法为本领域已知的所有合适种子处理技术,尤其是拌种技术,例如种子涂覆(例如种子压丸)、种子撒粉和种子吸胀(例如种子浸泡)。在本文中,“种子处理”是指使种子与本发明化合物彼此接触的所有方法,且“拌种”是指向种子提供一定量的本发明化合物的种子处理方法,即其产生包含本发明化合物的种子。在原则上,可在种子收获后至播种种子期间任何时间对种子进行处理。可在紧邻种植种子之前或在种植种子期间使用(例如)“播种箱”方法来处理种子。然而,还可在种植种子之前若干周或若干个月(例如至多12个月)(例如)以拌种处理形式进行处理,其中未观察到效能显著降低。
可方便地对未播种种子进行处理。本文所用术语“未播种种子”意指包括从种子收获至对植物萌芽和生长而言将种子播种于土地中期间任何阶段的种子。
具体而言,在处理中遵循一定程序,其中在合适装置(例如用于混合固体或固/液混合配对的混合装置)中将种子与所需量的未经处理或事先用水稀释的种子处理配制剂混合直至该组合物在种子上均匀分布。若合适,这之后为干燥步骤。
实施例
A.制备实施例
适当改变起始材料,使用下文合成实施例中所给出的程序来获得其他化合物I。以此方式获得的化合物与物理数据一起列于下表中。
下文所示产物由下列来表征:熔点测定、NMR光谱或通过HPLC-MS或HPLC光谱测定的质量([m/z])或停留时间(RT;[min.])。
HPLC-MS=高效液相色谱连用质谱;HPLC法:
方法1:RP-18柱(来自德国Merck KgaA的Speed ROD),50*4.6mm;移动相:乙腈+0.1%三氟乙酸(TFA)/水+0.1%TFA,使用在40℃下经5分钟5:95至100:0的梯度。流动速度1.8ml/min。
方法2:Phenomenex Kinetex 1.7μm XB-C18 100A;50×2.1mm;移 动相:A:水+0.1%三氟乙酸(TFA);B:乙腈+0.1%TFA;梯度:在1.50分钟内5%至100%B;100%B0.20min;流动:在1.50分钟内0.8ml/min至1.0ml/min,在60℃下。MS:四极电喷雾电离,80V(正离子模式)。
方法3:柱:IA 5μm-250×4.6mm;移动相:庚烷/二氯甲烷/乙醇/二乙胺50/50/1/0.1;流动:1ml/min;检测:UV 280nm;25℃。
方法4:柱:IC 5μm-250×4.6mm;移动相:乙醇/甲醇50/50;流动:0.7ml/min;检测:UV 280nm;25℃。
实施例1:5-甲基-1-(2,2,2-三氟-1-三氟甲基乙基)-1H-吡唑-4-甲酸哒嗪-4-基酰胺[I-34]的制备
在0℃下向398mg 5-甲基-1-[2,2,2-三氟-1-(三氟甲基)乙基]吡唑-4-羰基氯于10ml CH2Cl2中的溶液中滴加185mg哒嗪-4-胺和750mg三乙胺于30ml CH2Cl2中的溶液。在20℃至25℃下将混合物搅拌约68h,用25ml乙酸乙酯稀释,用3×15ml饱和NH4Cl水溶液洗涤,经MgSO4干燥并蒸发。通过快速层析(CH2Cl2/MeOH)来进行纯化,得到160mg标题化合物(纯度为90%)。HPLC-MS(方法1):RT 2.278min,m/z[MH]+354.1。
实施例2:N,5-二甲基-N-哒嗪-4-基-1-[2,2,2-三氟-1-(三氟甲基)乙基]吡唑-4-甲酰胺[I-38]的制备
在20℃至25℃下将300mg 5-甲基-1-[2,2,2-三氟-1-(三氟甲基)乙基]吡唑-4-甲酸、127mg N-甲基哒嗪-4-胺、710mg O-(7-氮杂苯并三唑-1-基)-N,N,N',N'-四甲基脲六氟磷酸盐[HATU]和220mg三乙胺于30ml THF中的混合物搅拌约24h,然后蒸发。将残余物吸收于21ml CH2Cl2中,用3×14ml水洗涤,经Na2SO4干燥,然后蒸发。通过快速层析(CH2Cl2/MeOH)来进行纯化,得到130mg标题化合物(纯度为90%)。
HPLC-MS(方法1):RT 2.271min,m/z[MH]+368.1。
实施例3:在以下条件下通过制备型层析来进行对映体I-381与I-382的分离:柱:AD-H 5μm-250×30mm;移动相:二氧化碳/乙醇90/10;流动:120ml/min;检测:UV 280nm;背压:150巴;温度: 25℃。
2g粗制材料I-377得到978mg(+)-对映体I-381和972mg(-)-对映体I-382,各自>99%ee。
实施例4:在以下条件下通过制备型层析来进行对映体I-383和I-384的分离:IC 5μm-250×30mm;移动相:二氧化碳/乙醇70/30;流动:120ml/min;检测:UV 280nm;背压:150巴;温度:25℃。
2g粗制材料I-373得到864mg(+)-对映体I-383(98.4%ee)和898mg(-)-对映体I-384(98.0%ee)。
表I-式I化合物(异构体T-A)
缩写:
<DOT>:二氧代硫杂环丁基
<OTT>:氧代硫杂环丁基
<TP>:四氢吡喃基
<DT>:二噻烷基
<PY>:吡啶基
<TT>:硫杂环丁基
<OTL>:氧杂硫杂环戊基
<TN>:噻吩基
<TZ>:噻唑基
(A)、(B):分别为非对映体A和B
(S):三氟乙酸盐
(E+):(+)-对映体
(E-):(-)-对映体
B.生物学实施例
可在下文所述生物学测试中证实并评价本发明式I化合物的活性。
若无其他说明,则测试溶液如下制备:
将活性化合物以所需浓度溶于1:1(体积:体积)蒸馏水:丙酮的混合物中。在使用当天且通常以ppm(wt/vol)浓度制备测试溶液。
B.1豇豆蚜(Aphis craccivora)
在记录害虫种群后对盘踞有100-150只蚜虫的不同阶段的盆栽豇豆植株进行喷雾。在24、72和120小时后评估种群减少。
在该测试中,与未经处理的对照相比,化合物I-1、I-2、I-3、I-4、I-5、I-6、I-7、I-8、I-9、I-10、I-11、I-12、I-13、I-14、I-15、I-16、I-17、I-18、I-19、I-20、I-21、I-22、I-23、I-24、I-25、I-26、I-27、I-28、I-29、I-30、I-31、I-32、I-33、I-34、I-35、I-36、I-37、I-38、I-39、I-40、I-41、I-42、I-43、I-44、I-45、I-46、I-47、I-48、I-50、I-51、I-52、I-53、I-54、I-55、I-56、I-57、I-58、I-59、I-60、I-61、I-62、I-63、I-64、I-65、I-66、I-67、I-68、I-69、I-70、I-71、I-72、I-74、I-75、I-76、I-77、I-78、I-79、I-80、 I-81、I-82、I-83、I-84、I-85、I-86、I-87、I-88、I-91、I-92、I-93、I-94、I-95、I-96、I-97、I-98、I-99、I-100、I-101、I-102、I-103、I-104、I-105、I-106、I-107、I-108、I-109、I-110、I-111、I-112、I-113、I-114、I-115、I-116、I-117、I-118、I-119、I-120、I-121、I-122、I-123、I-124、I-125、I-126、I-127、I-128、I-129、I-130、I-131、I-132、I-133、I-134、I-135、I-136、I-137、I-138、I-139、I-140、I-141、I-142、I-143、I-144、I-145、I-146、I-147、I-148、I-149、I-150、I-151、I-152、I-153、I-154、I-155、I-156、I-157、I-158、I-159、I-160、I-161、I-162、I-163、I-164、I-166、I-167、I-168、I-169、I-170、I-171、I-172、I-173、I-174、I-175、I-176、I-177、I-178、I-179、I-180、I-181、I-182、I-183、I-184、I-185、I-186、I-187、I-188、I-189、I-190、I-191、I-192、I-193、I-194、I-195、I-196、I-197、I-198、I-199、I-200、I-201、I-202、I-203、I-204、I-205、I-211、I-212、I-214、I-215、I-216、I-218、I-219、I-220、I-221、I-222、I-223、I-224、I-230、I-231、I-232、I-233、I-235、I-236、I-237、I-238、I-239、I-240、I-241、I-244、I-245、I-246、I-247、I-249、I-250、I-251、I-252、I-253、I-254、I-255、I-256、I-257、I-258、I-259、I-260、I-261、I-262、I-263、I-264、I-265、I-266、I-267、I-268、I-269、I-270、I-271、I-272、I-273、I-274、I-275、I-276、I-277、I-278、I-279、I-280、I-281、I-282、I-283、I-284、I-285、I-286、I-287、I-288、I-289、I-290、I-291、I-292、I-293、I-294、I-295、I-296、I-297、I-298、I-299、I-300、I-301、I-302、I-303、I-304、I-305、I-306、I-307、I-308、I-309、I-310、I-311、I-312、I-313、I-314、I-315、I-316、I-317、I-366、I-367、I-368、I-369、I-370、I-371、I-372、I-373、I-374、I-375、I-376、I-377、I-378、I-379、I-380、I-381、I-382、I-383和I-384在500ppm下显示至少75%的死亡率。
B.2棉蚜(Aphis gossypii,混合生命期)
在环己酮中将活性化合物配制为10,000ppm溶液,供应于1.3ml 管中。这些管插入安装有雾化喷嘴的自动静电喷雾器中且其用作储备溶液,用于在1:1(体积:体积)水:丙酮中制成更低浓度的稀释液。将非离子型表面活性剂以0.01%(v/v)体积包括在该溶液中。
在处理前,通过将来自主蚜虫群体的重度侵染的叶置于各子叶的顶部上以使子叶阶段的棉花植株用蚜虫侵染。使蚜虫经整夜转移以实现每棵植株80-100个蚜虫侵染并移走宿主叶。然后通过安装有雾化喷嘴的自动静电植物喷雾器对侵染植株进行喷雾。在喷雾器通风橱中干燥植株,将其从喷雾器中取出,且然后在25℃和20-40%相对湿度下在生长室中维持在荧光光照下24小时光照期。5天后,相对于未经处理的对照植株上蚜虫的死亡率测定经处理植株上的死亡率。
在该测试中,与未经处理的对照相比,化合物I-1、I-4、I-5、I-6、I-7、I-9、I-10、I-11、I-12、I-13、I-14、I-15、I-16、I-17、I-18、I-20、I-21、I-22、I-23、I-24、I-26、I-27、I-28、I-29、I-30、I-31、I-32、I-33、I-35、I-36、I-38、I-39、I-42、I-43、I-44、I-45、I-46、I-47、I-48、I-51、I-60、I-61、I-62、I-63、I-64、I-66、I-67、I-75、I-76、I-77、I-78、I-79、I-80、I-81、I-83、I-85、I-87、I-88、I-90、I-91、I-92、I-93、I-94、I-95、I-96、I-97、I-98、I-99、I-100、I-101、I-102、I-103、I-104、I-105、I-106、I-107、I-109、I-112、I-114、I-115、I-116、I-117、I-118、I-119、I-120、I-121、I-125、I-129、I-131、I-133、I-134、I-135、I-136、I-137、I-138、I-140、I-141、I-142、I-143、I-144、I-145、I-147、I-148、I-149、I-150、I-151、I-152、I-155、I-157、I-166、I-167、I-168、I-169、I-170、I-173、I-174、I-181、I-182、I-183、I-184、I-185、I-186、I-188、I-189、I-190、I-191、I-192、I-193、I-195、I-196、I-197、I-198、I-199、I-200、I-201、I-202、I-203、I-204、I-205、I-211、I-212、I-232、I-233、I-238、I-265、I-271、I-277、I-290、I-300、I-302、I-307、I-366、I-367、I-368、I-369、I-370、I-371、I-372、I-373、I-374、I-375、I-376、I-377、I-378、I-379、I-380、I-381、I-382、I-383和I-384在10ppm下显示至少75%的死亡率。
B.3银叶粉虱(Bemisia argentifolii,成虫)
在环己酮中将活性化合物配制为10,000ppm溶液,供应于1.3ml 管中。这些管插入安装有雾化喷嘴的自动静电喷雾器中且其用作储备溶液,用于在1:1(体积:体积)水:丙酮中制成更低浓度的稀释液。将非离子型表面活性剂以0.01%(v/v)体积包括在该溶液中。
通过安装有雾化喷嘴的自动静电植物喷雾器对子叶阶段的棉花植株(1棵植株/盆)进行喷雾。在喷雾器通风橱中干燥植株且然后将其从喷雾器中取出。将各盆置于塑料杯中并引入10-12只粉虱成虫(约3至5天龄)。使用抽吸器和连接至防护移液管头的0.6cm无毒管(R-3603)收集昆虫。然后,将含有所收集昆虫的该管头轻轻插入含有经处理植株的土壤中,使昆虫爬出该管头到达叶面上取食。用可重复使用的筛盖(150微米目的聚酯筛网PeCap,来自Tetko公司)覆盖杯子。在25℃和20-40%相对湿度下将测试植株在生长室中维持3天,避免直接暴露于荧光灯(24小时光照期)下以防止杯内热量截留。在处理后3天评估死亡率,将其与未经处理的对照植株进行比较。
在该测试中,与未经处理的对照相比,化合物I-4、I-5、I-6、I-7、I-8、I-9、I-10、I-11、I-12、I-13、I-14、I-18、I-20、I-21、I-22、I-23、I-24、I-27、I-28、I-29、I-30、I-31、I-32、I-33、I-35、I-39、I-43、I-46、I-61、I-63、I-67、I-68、I-76、I-79、I-85、I-87、I-88、I-90、I-91、I-92、I-93、I-94、I-96、I-97、I-98、I-102、I-103、I-104、I-105、I-109、I-113、I-115、I-128、I-129、I-133、I-135、I-137、I-138、I-139、I-142、I-143、I-144、I-145、I-146、I-148、I-149、I-153、I-155、I-157、I-167、I-168、I-169、I-173、I-177、I-181、I-182、I-183、I-184、I-188、I-190、I-198、I-201、I-202、I-204、I-238、I-260、I-266、I-277、I-292、I-366、I-367、I-368、I-369、I-370、I-371、I-372、I-376、I-377、I-379和I-380在10ppm下显示至少75%的死亡率。
B.4巢菜修尾蚜(Vetch aphid,Megoura viciae)
在3:1(体积:体积)水:DMSO中以不同经配制化合物浓度配制活性化合物。
将豆叶盘置于填充有0.8%琼脂和2.5ppm OPUSTM的微滴定板中。用2.5μl测试溶液喷雾叶盘并将5-8只成年蚜虫置于微滴定板中,然后封闭微滴定板并在23±1℃和50±5%的相对湿度下于荧光灯下保持6天。基于存活且繁殖的蚜虫评估死亡率。然后目测评价蚜虫的死亡率和繁殖力。
在该测试中,与未经处理的对照相比,化合物I-1、I-2、I-3、I-4、I-5、 I-6、I-7、I-8、I-9、I-10、I-11、I-12、I-13、I-14、I-15、I-16、I-17、I-18、I-19、I-20、I-21、I-22、I-23、I-24、I-25、I-26、I-27、I-28、I-29、I-30、I-31、I-32、I-33、I-34、I-35、I-36、I-38、I-41、I-42、I-43、I-44、I-45、I-46、I-47、I-48、I-49、I-50、I-51、I-52、I-53、I-54、I-55、I-57、I-58、I-59、I-60、I-61、I-62、I-63、I-64、I-65、I-66、I-67、I-68、I-69、I-70、I-71、I-72、I-74、I-75、I-76、I-77、I-78、I-79、I-80、I-81、I-82、I-83、I-84、I-85、I-86、I-87、I-88、I-91、I-92、I-93、I-94、I-95、I-96、I-97、I-98、I-99、I-100、I-101、I-102、I-103、I-104、I-105、I-106、I-107、I-108、I-109、I-112、I-113、I-114、I-115、I-116、I-117、I-118、I-119、I-120、I-121、I-122、I-123、I-124、I-125、I-126、I-127、I-128、I-129、I-130、I-131、I-132、I-133、I-134、I-135、I-136、I-137、I-138、I-140、I-141、I-142、I-143、I-144、I-145、I-146、I-152、I-154、I-155、I-156、I-157、I-158、I-159、I-161、I-162、I-163、I-164、I-165、I-166、I-173、I-174、I-181、I-182、I-183、I-184、I-185、I-194、I-195、I-196、I-197、I-218、I-219、I-220、I-221、I-222、I-223、I-224、I-225、I-226、I-227、I-228、I-229、I-230、I-231、I-232、I-233、I-234、I-242、I-244、I-245、I-246、I-247、I-248、I-256、I-270、I-271、I-272、I-273、I-274、I-275、I-289、I-304、I-305、I-306、I-307、I-308、I-309、I-311、I-312、I-366、I-367、I-368、I-369、I-370、I-371、I-372、I-373、I-374、I-375、I-376、I-377、I-378、I-379、I-380、I-381、I-382、I-383和I-384在2500ppm下显示至少75%的死亡率。
B.5绿桃蚜(Myzus persicae)
在环己酮中将活性化合物配制为10,000ppm溶液,供应于1.3ml 管中。这些管插入安装有自动喷嘴的自动静电喷雾器中且其用作储备溶液,用于在1:1(体积:体积)水:丙酮中制成更低浓度的稀释液。将非离子型表面活性剂以0.01%(v/v)体积包括在该溶液中。
在处理前通过将来自主群体的重度侵染的叶置于处理植株顶部上来侵染第一真叶阶段柿子椒植株。使蚜虫经整夜转移以实现每棵植株30-50只蚜虫侵染并移走宿主叶。然后通过安装有雾化喷嘴的自动静电植物喷雾器 对侵染植株进行喷雾。在喷雾器通风橱中干燥植株,取出,且然后在25℃和20-40%相对湿度下在24小时光照期中在荧光光照下使其维持在生长室中。5天后,相对于对照植株上蚜虫的死亡率测定经处理植株上的死亡率。
在该测试中,与未经处理的对照相比,化合物I-1、I-2、I-4、I-5、I-6、I-7、I-8、I-9、I-10、I-11、I-12、I-13、I-14、I-15、I-16、I-17、I-18、I-19、I-20、I-21、I-22、I-23、I-24、I-27、I-28、I-29、I-30、I-31、I-32、I-33、I-34、I-35、I-36、I-37、I-38、I-39、I-42、I-43、I-44、I-45、I-46、I-47、I-48、I-50、I-60、I-61、I-62、I-63、I-64、I-66、I-67、I-69、I-71、I-74、I-75、I-76、I-77、I-78、I-79、I-80、I-81、I-82、I-83、I-84、I-85、I-86、I-87、I-88、I-89、I-90、I-91、I-92、I-93、I-94、I-95、I-96、I-97、I-98、I-99、I-100、I-101、I-102、I-103、I-104、I-105、I-106、I-107、I-108、I-109、I-110、I-111、I-112、I-114、I-115、I-116、I-117、I-118、I-120、I-121、I-124、I-125、I-126、I-127、I-128、I-129、I-130、I-131、I-132、I-133、I-134、I-135、I-136、I-137、I-138、I-140、I-141、I-142、I-143、I-144、I-145、I-146、I-147、I-148、I-149、I-150、I-151、I-152、I-153、I-155、I-157、I-167、I-168、I-169、I-170、I-173、I-174、I-176、I-177、I-181、I-183、I-184、I-185、I-186、I-188、I-189、I-190、I-191、I-192、I-193、I-194、I-195、I-196、I-197、I-198、I-199、I-200、I-201、I-202、I-203、I-204、I-205、I-211、I-212、I-232、I-238、I-251、I-265、I-266、I-271、I-277、I-284、I-288、I-290、I-291、I-292、I-293、I-300、I-302、I-303、I-307、I-366、I-367、I-368、I-369、I-370、I-371、I-372、I-373、I-374、I-375、I-376、I-377、I-378、I-379、I-380、I-381、I-382、I-383和I-384在10ppm下显示至少75%的死亡率。
B.6墨西哥棉铃象(Anthonomus grandis)
在3:1(体积:体积)水:DMSO中配制化合物。
为评价墨西哥棉铃象(Anthonomus grandis)的防治,测试单元由含有昆虫膳食和20-30只墨西哥棉铃象卵的24孔微滴定板组成。使用定制微喷雾器以20μl的量将不同浓度的经配制化合物喷雾至昆虫膳食上,重复两次。施加后,在23±1℃和50±5%相对湿度下将微滴定板温育5天。然后 目测评价卵和幼虫的死亡率。
在该测试中,与未经处理的对照相比,化合物I-67、I-85、I-92、I-94、I-95、I-96、I-98、I-102、I-104、I-113、I-127、I-132、I-137、I-143、I-182、I-374、I-377和I-380在2500ppm下显示至少75%的死亡率。
B.7稻飞虱(Nilaparvata lugens)
在喷雾前将稻幼苗清洁并洗涤24小时。在1:1(体积:体积)水:丙酮中配制活性化合物并添加0.1%(体积/体积)表面活性剂(EL 620)。用5ml测试溶液喷雾盆栽稻幼苗,风干,将其置于笼中并用10只成虫进行接种。将经处理稻植株保持在28-29℃和50-60%的相对湿度下。在72小时后记录百分比死亡率。
在该测试中,与未经处理的对照相比,化合物I-8、I-9、I-10、I-11、I-25、I-29、I-35、I-62、I-63、I-68、I-113、I-141、I-143、I-199、I-204、I-245、I-312和I-371在500ppm下显示至少75%的死亡率。
B.8兰花蓟马(Dichromothrips corbetti)
将活性化合物配制为1:1(体积:体积)水:丙酮溶液。以0.1%(体积/体积)的比率添加表面活性剂(Alkamuls EL 620)。在喷雾前,将兰花瓣清洁,洗涤并风干。将花瓣浸于测试溶液中3秒,风干,置于可重新密封的塑料内部并用20只成虫进行接种。在28-29℃和50-60%相对湿度下将经处理花瓣保持在保存室内部。在72小时后记录百分比死亡率。
在该测试中,与未经处理的对照相比,化合物I-4、I-35、I-39、I-43、I-78、I-83、I-86、I-94、I-95、I-96、I-107、I-109、I-115、I-132、I-133、I-142、I-143、I-146、I-154、I-158、I-168、I-184、I-186、I-187、I-189、I-191、I-193、I-198、I-201、I-202、I-203、I-204、I-205、I-278、I-279、I-280、I-281、I-297、I-298、I-299、I-300、I-305、I-306、I-308、I-310、I-370和I-373在500ppm下显示至少75%的死亡率。
B.9黑尾叶蝉(Rice green leafhopper,Nephotettix virescens)
在喷雾前将稻幼苗清洁并洗涤24小时。在1:1(体积:体积)水:丙酮中配制活性化合物,并添加0.1%体积/体积表面活性剂(EL 620)。用5ml测试溶液喷雾盆栽稻幼苗,风干,将其置于笼中并用10只成虫进行接种。 将经处理稻植株保持在28-29℃和50-60%的相对湿度下。在72小时后记录百分比死亡率。
在该测试中,与未经处理的对照相比,化合物I-7、I-8、I-10、I-11、I-32、I-33、I-63、I-79、I-113和I-199在500ppm下显示至少75%的死亡率。
B.10菜蛾(Plutella xylostella)
在1:1(体积:体积)水:丙酮和0.1%(体积:体积)Alkamuls EL 620表面活性剂中配制活性化合物。将6cm卷心菜叶的叶盘浸于测试溶液中3秒并使其在与润湿滤纸对齐的Petri板中风干。用10只第三龄幼虫对叶盘进行接种并在25-27℃和50-60%湿度下保持3天。在处理72h后评估死亡率。
通过以下比较实验来证实本发明化合物的有益活性优于现有技术已知的在结构上类似的化合物:
这些表显示与未经处理的对照相比的%死亡率。
*)FD=摄食损害(feeding damage)
Claims (23)
1.式I的吡唑化合物及其立体异构体、盐或互变异构体:
其中
U为N或CH;
T为O或S;
R1为H、C1-C2烷基或C1-C2烷氧基-C1-C2烷基;
R2为CH3;
R3为C2-C6烷基、C1-C6卤代烷基、C1-C2烷氧基-C1-C2烷基、C2-C6链烯基、C3-C6环烷基、CN,其中C原子可未经取代,或部分地或完全经Ra取代;
Ra为卤素、CN、C1-C2烷基、C1-C2卤代烷基或S(O)nRb;
n为0、1或2;
Rb为C1-C2烷基,
R4为C1-C4烷基,C1-C6卤代烷基或C3-C6环烷基;
R5为H,C1-C4烷基,CN或C1-C6卤代烷基;
R3和R4可一起形成3-6员碳环或杂环,其可含有1或2个选自N-Rc、O和S的杂原子,其中S可经氧化,所述碳环或杂环可经Ra取代;
Rc为氢、C1-C2烷基、C1-C2烷基羰基或C1-C2烷氧基羰基,
其中,该式I的吡唑化合物不包括其中T为O,R1为H、C1-C2烷基或CH2OCH3,R2为CH3,R3为CF3或环丙基,R4为CH3,且R5为H的外消旋化合物。
2.根据权利要求1的式I化合物,其中U为CH。
3.根据权利要求1的式I化合物,其中U为N。
4.根据权利要求1的式I化合物,其中T为O。
5.根据权利要求1-4中任一项的式I化合物,其中R1为H、C1-C2烷 基或C1-C2烷氧基甲基。
6.根据权利要求1-4中任一项的式I化合物,其中R1为H或C1-C2烷基。
7.根据权利要求1-4中任一项的式I化合物,其中R3为CN、C2-C6烷基、C1-C2卤代烷基、C1-C2烷氧基-C1-C2烷基或C3-C6环烷基,其中C原子可经取代。
8.根据权利要求5的式I化合物,其中R3为CN、C2-C6烷基、C1-C2卤代烷基、C1-C2烷氧基-C1-C2烷基或C3-C6环烷基,其中C原子可经取代。
9.根据权利要求1-4中任一项的式I化合物,其中R3为C2-C6烷基、C1-C2卤代烷基或C3-C6环烷基,其中C原子可经取代。
10.根据权利要求5的式I化合物,其中R3为C2-C6烷基、C1-C2卤代烷基或C3-C6环烷基,其中C原子可经取代。
11.根据权利要求1-4中任一项的化合物,其中R4为C1-C4烷基、C1-C4卤代烷基或C3-C6环烷基。
12.根据权利要求8或10的化合物,其中R4为C1-C4烷基、C1-C4卤代烷基或C3-C6环烷基。
13.根据权利要求1-4中任一项的化合物,其中R4为CH3。
14.根据权利要求12的化合物,其中R4为CH3。
15.根据权利要求1-4中任一项的化合物,其中R5为H或CH3。
16.根据权利要求12的化合物,其中R5为H或CH3。
17.根据权利要求14的化合物,其中R5为H或CH3。
18.一种组合物,包含至少一种根据权利要求1-17中任一项的化合物和至少一种惰性液体和/或固体载体。
19.一种防治动物害虫的农业组合物,包含至少一种如权利要求1-17中任一项所定义的化合物和至少一种惰性液体和/或固体可接受的载体和若需要至少一种表面活性剂。
20.一种防除或防治无脊椎动物害虫的方法,所述方法包含使所述害虫或其食物供应源、栖息地或繁殖地与杀虫有效量的至少一种如权利要求1-17中任一项所定义的化合物接触。
21.一种保护生长中植物以防无脊椎动物害虫侵袭或侵染的方法,所述方法包含使植物或其中所述植物生长的土壤或水与杀虫有效量的至少一种如权利要求1-17中任一项所定义的化合物接触。
22.一种处理种子的方法,其中以0.1g至10kg/100kg种子的量将如权利要求1-17中任一项所定义的化合物或其对映体、非对映体或盐施用于种子。
23.如权利要求1-17中任一项所定义的化合物在保护生长中植物以防无脊椎动物害虫侵袭或侵染中的用途。
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