CN1476428A - 用作农药的△1-吡咯啉类化合物 - Google Patents
用作农药的△1-吡咯啉类化合物 Download PDFInfo
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- CN1476428A CN1476428A CNA018193099A CN01819309A CN1476428A CN 1476428 A CN1476428 A CN 1476428A CN A018193099 A CNA018193099 A CN A018193099A CN 01819309 A CN01819309 A CN 01819309A CN 1476428 A CN1476428 A CN 1476428A
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- Prior art keywords
- formula
- alkyl
- compound
- haloalkyl
- definition
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- 150000004064 1-pyrrolines Chemical class 0.000 title claims description 11
- 239000000575 pesticide Substances 0.000 title description 4
- 238000000034 method Methods 0.000 claims abstract description 84
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 16
- 150000003236 pyrrolines Chemical class 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 175
- -1 4Be halogen Chemical class 0.000 claims description 132
- 238000002360 preparation method Methods 0.000 claims description 44
- 239000003795 chemical substances by application Substances 0.000 claims description 43
- 239000011737 fluorine Substances 0.000 claims description 34
- 229910052731 fluorine Inorganic materials 0.000 claims description 34
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 31
- 239000000460 chlorine Substances 0.000 claims description 28
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052796 boron Inorganic materials 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
- 239000011230 binding agent Substances 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 8
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 7
- 239000013543 active substance Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 208000032825 Ring chromosome 2 syndrome Diseases 0.000 claims description 6
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 0.000 claims description 4
- 230000006103 sulfonylation Effects 0.000 claims description 4
- 238000005694 sulfonylation reaction Methods 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 239000003905 agrochemical Substances 0.000 claims 3
- 230000002508 compound effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 7
- 239000013067 intermediate product Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 75
- 241000196324 Embryophyta Species 0.000 description 68
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- 239000002904 solvent Substances 0.000 description 50
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- 239000003995 emulsifying agent Substances 0.000 description 39
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
- 239000000463 material Substances 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 34
- 238000012360 testing method Methods 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 239000002585 base Substances 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- 230000000694 effects Effects 0.000 description 25
- 238000004128 high performance liquid chromatography Methods 0.000 description 25
- 239000000047 product Substances 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 241000238631 Hexapoda Species 0.000 description 20
- 238000009472 formulation Methods 0.000 description 19
- 239000002994 raw material Substances 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 17
- 239000003921 oil Substances 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 16
- 241000894006 Bacteria Species 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 150000003851 azoles Chemical class 0.000 description 14
- 239000012071 phase Substances 0.000 description 14
- 244000299507 Gossypium hirsutum Species 0.000 description 13
- 125000002877 alkyl aryl group Chemical group 0.000 description 13
- 229920000151 polyglycol Polymers 0.000 description 13
- 239000010695 polyglycol Substances 0.000 description 13
- 241001124076 Aphididae Species 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 229920000742 Cotton Polymers 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 240000008042 Zea mays Species 0.000 description 12
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 12
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 12
- 235000005822 corn Nutrition 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 240000007124 Brassica oleracea Species 0.000 description 10
- 230000003373 anti-fouling effect Effects 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
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- 229910052760 oxygen Inorganic materials 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- 244000068988 Glycine max Species 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
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- 231100000225 lethality Toxicity 0.000 description 9
- 229940031815 mycocide Drugs 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
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- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 8
- 235000010469 Glycine max Nutrition 0.000 description 8
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 8
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- 239000012141 concentrate Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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- DPOWHSMECVNHAT-YERPJTIDSA-N tetcyclacis Chemical compound C1=CC(Cl)=CC=C1N1[C@H]2[C@H]([C@@H]3[C@H]4N=N3)C[C@H]4[C@H]2N=N1 DPOWHSMECVNHAT-YERPJTIDSA-N 0.000 description 1
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- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
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- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- WVZPYZMQQDNINJ-UHFFFAOYSA-N tributyl(butylstannyloxy)stannane Chemical compound CCCC[SnH](CCCC)O[SnH](CCCC)CCCC WVZPYZMQQDNINJ-UHFFFAOYSA-N 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-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
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 241000701451 unidentified granulovirus Species 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 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
- 239000003799 water insoluble solvent Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
-
- A—HUMAN NECESSITIES
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Abstract
本发明涉及式(I)的新的Δ1-吡咯啉类化合物,上述物质的多种制备方法,及其防治有害动物的用途和新的中间体,其中R1、R2、R3、R4、R5、n、r和s为说明书中给出的定义。
Description
本发明涉及新的Δ1-吡咯啉类化合物,其多种制备方法及其用作农药的用途。
已知Δ1-吡咯啉类化合物具有多种杀虫活性(参见:WO00/21958、WO99/59968、WO99/59967和WO98/22438)。上述物质具有良好的活性;可是它们在有些情况下并不令人满意。
其中
n为0或1,
r和s各自独立地为0,1或2,
R1为卤素或甲基,
R2为氢或卤素,
R3和R4各自独立地为卤素、烷基、卤代烷基、烷氧基或卤代烷氧基,
R5为烷基、卤代烷基、各自任选被W1所列的相同或不同的基团单-或多取代的苯基或代表-NR6R7,
W1为卤素、烷基、卤代烷基、烷氧基、卤代烷氧基、烷基羰基、烷氧基羰基或-S(O)qR8,
R6为烷基或卤代烷基,
R7为氢、烷基或卤代烷基,
R6和R7还一起代表亚烷基或烷氧基亚烷基,
R8为烷基或卤代烷基和
q为0,1或2。
而且,已发现式(I)的Δ1-吡咯啉类化合物是通过下述方法制备的:
(A)用路易斯酸或质子酸处理式(II)的氨基酮
其中
R1、R2、R3、R4、R5、n、r和s为上述给出的定义,
或
(B)如果需要在酸结合剂和如果需要在稀释剂存在下,式(III)的(联)苯酚化合物与磺酰化试剂反应
其中
R1、R2、R3、R4、n、r和s为上述给出的定义,
或
其中
R1、R2、R3、R4、R5、r和s为上述给出的定义,
其制备首先是通过式(IV)的吡咯啉类化合物与二硼酸酯在催化剂存在下、在酸结合剂存在下反应且,如果需要在稀释剂存在下进行反应,
其中
R1、R2、R3、和r为上述给出的定义,和
X为Br、Cl、I、-OSO2CF3或-OSO2(CF2)3CF3,
且,如果需要在先分离所得的式(V)化合物后,式(V)化合物与式(VI)的碘化物在催化剂存在下、在二硼酸酯存在下、在酸结合剂存在下反应,且如果需要,在稀释剂存在下反应,
其中
R1、R2、R3和r为上述给出的定义和
G代表4,4,5,5-四甲基-1,3,2-二氧杂硼杂戊环(borolan)-2-基、5,5-二甲基-1,3,2-二氧杂硼杂己环(borinan)-2基、4,4,6-三甲基-1,3,2-二氧杂硼杂己环-2-基或1,3,2-苯并二氧杂硼杂戊烯(borol)-2-基,
其中
R4和R5和s为上述定义。
最后,已发现本发明式(I)化合物具有非常好的杀虫活性并可在作物保护和材料保护中用于防治有害动物,如昆虫。
令人惊奇的是,本发明式(I)的Δ1-吡咯啉类化合物的杀虫活性,与相同作用目的、结构非常相似的现有技术中的Δ1-吡咯啉类化合物相比要好许多。
式(I)提供了本发明Δ1-吡咯啉类化合物的一般定义。
n优选为0或1。
r和s各自独立地优选为0,1或2。
R1优选为氟、氯、溴或甲基。
R2优选为氢、氟、氯或溴。
R3和R4各自独立地优选为氟、氯、溴、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基或C1-C6卤代烷氧基。
R5优选为C1-C6烷基、C1-C6卤代烷基、各自任选被W1所列的相同或不同的基团单-至四取代的苯基或代表-NR6R7。
W1优选为氟、氯、溴、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷基羰基、C1-C6烷氧基羰基或-S(O)qR8。
R6优选为C1-C6烷基或C1-C6卤代烷基。
R7优选为氢、C1-C6烷基或C1-C6卤代烷基。
R6和R7还一起优选代表C3-C6亚烷基或C1-C4-烷氧基-C1-C4亚烷基。
R8优选为C1-C6-烷基或C1-C6-卤代烷基。
q优选为0,1或2。
n特别优选为0或1。
r和s各自独立地特别优选为0,1或2。
R1特别优选为氟、氯或甲基。
R2特别优选为氢、氟或氯。
R3和R4各自独立地特别优选为氟、氯、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基。
R5特别优选为C1-C4烷基、C1-C4卤代烷基、各自任选被W1所列的相同或不同的基团单-至三取代的苯基或代表-NR6R7。
W1特别优选为氟、氯、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷基羰基、C1-C4烷氧基羰基或-S(O)qR8。
R6特别优选为C1-C4烷基或C1-C4卤代烷基。
R7特别优选为氢、C1-C4烷基或C1-C4卤代烷基。
R6和R7还一起特别优选代表C4-C5亚烷基或-(CH2)2-O-(CH2)2-。
R8特别优选为C1-C4-烷基或C1-C4-卤代烷基。
q特别优选为0,1或2。
n更特别优选为0或1。
r和s各自独立地更特别优选为0或1。
R1更特别优选为氟或氯。
R2更特别优选为氢或氟。
R3和R4各自独立地更特别优选为氟、氯、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、三氟甲基、三氟乙基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、三氟甲氧基或三氟乙氧基。
R5更特别优选为甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、三氟甲基、三氟乙基、壬氟丁基、各自任选被W1所列的相同或不同的基团单-至二取代的苯基或代表-NR6R7。
W1更特别优选为氟、氯、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、三氟甲基、三氟乙基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、三氟甲氧基、三氟乙氧基、-COCH3、-CO2CH3、-SCF3、-SCHF2、-SOCF3、-SOCHF2、-SO2CF3或-SO2CHF2。
R6更特别优选为甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、三氟甲基或三氟乙基。
R7更特别优选为氢、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、三氟甲基或三氟乙基。
其中
R1、R2、R3、R4、R5、r和s为上述给出的定义,
其中
R1、R2、R4、R5和s为上述给出的定义,
而且,优选式(I-a)和(I-b)化合物,其中的R1、R2、R3、R4、R5、r和s具有上述给出的优选定义。
而且,优选式(I-a)和(I-b)化合物,其中的R1、R2、R3、R4、R5、r和s具有上述给出的特别优选定义。
而且,优选式(I-a)和(I-b)化合物,其中的R1、R2、R3、R4、R5、r和s具有上述给出的更特别优选定义。
而且,更特别优选下述给出的式(I-c)(R)-构型化合物
其中
R1、R2、R4、R5和s为上述给出的定义。
而且,更特别优选下述给出的式(I-d)(R)-构型化合物
其中,R1、R2、R3、R4、R5、r和s为上述给出的定义。
式(I-c)和(I-d)的纯对映体化合物是通过拆分的常规方法制备的,例如在手性的固定相上色谱分离相应的外消旋物。以此方式可将外消旋的终产物和外消旋的中间体分别分离成两种对映体。
饱和烃基,如烷基,可以是直链或支链的,甚至在化合物中可能包括与之结合的杂原子,例如在烷氧基中。
可选择的取代基可以是单-或多取代,其中多取代时,取代基可以是相同或不同的。参数相同的多个取代基,例如s个取代基R4,s=2,可以是相同或不同的。
可是,上述一般的或优选基团定义或例示还可根据需要彼此组合,即,包括分别的范围和优选范围之间的任意组合。这些组合即适用于终产物,相应的还适用于原料和中间体。
使用4’-[5-(2,6-二氟苯基)-3,4-二氢-2H-吡咯-2-基]-1,1’-联苯-4-醇和三氟甲磺酰氯(F3CSO2Cl)为原料,根据本发明的方法(B)的过程可用下式表示:
使用5-(2,6-二氟苯基)-2-(4-溴苯基)-3,4-二氢-2H-吡咯,三氟甲磺酸4-碘苯基酯,钯催化剂和4,4,4’,4’,5,5,5’,5’-八甲基-2,2’-双-1,3,2-二氧杂硼杂戊环为原料,根据本发明的方法(C)可用下式表示:
方法和中间体的例示说明
方法(A)
式(II)提供了进行本发明方法(A)所需原料氨基酮的一般的定义。在上式中,R1、R2、R3、R4、R5、n、r和s各自优选、特别优选或更特别优选地为在对本发明式(I)化合物的说明中已经对这些基团作为优选、特别优选等的基团所提及的定义。
式(II)的氨基酮是新的。它们可通过下述方法制备:
a)式(VII)的N-Boc-内酰胺与式(VIII)金属化的芳香化合物反应
其中
R1和R2各自为上述定义和
M为Li、MgCl、MgBr、MgI或ZnCl,
如果需要反应在稀释剂(例如四氢呋喃)存在下,在-70℃至+70℃之间反应。
式(VII)提供了进行本发明方法(a)所需原料N-Boc-内酰胺的一般的定义。在上式中,R3、R4、R5、n、r和s各自优选、特别优选或更特别优选地为在对本发明式(I)化合物的说明中已经对这些基团作为优选、特别优选等的基团所提及的定义。
式(VII)的N-Boc-内酰胺是新的。例如它们可通过下述方法制备:
b)式(IX)的内酰胺在碱存在下(例如二甲基氨基吡啶)与联二碳酸二叔丁基酯反应,如果需要反应在稀释剂(例如二氯甲烷)存在下进行,
其中
R3、R4、R5、n、r和s各自为上述定义。
式(VIII)提供了进行本发明方法(a)所需原料金属化芳香化合物的一般的定义。在上式中,R1和R2各自的优选、特别优选和更特别优选定义为在对本发明式(I)化合物的说明中已经对于这些基团作为优选、特别优选等所提及的定义。M优选代表Li、MgCl、MgBr、MgI、ZnCl,特别优选代表Li、MgCl、MgBr、MgI,更特别优选代表Li、MgCl、MgBr。
一些式(VIII)的金属化芳香化合物是已知的,或可以通过已知方法制备的,例如通过锂化或格利雅反应从相应的芳香化合物或卤化芳香化合物制备。
式(IX)提供了进行本发明方法(b)所需原料内酰胺的一般的定义。在上式中,R3、R4、R5、n、r和s各自的优选、特别优选和更特别优选定义为在对本发明式(I)化合物的说明中已经对于这些基团作为优选、特别优选等所提及的定义。
式(IX)的内酰胺是新的。
式(IX-a)的内酰胺,例如可通过下述方法制备:
其中
R4、R5、r和s为上述定义,
其中R4和s为上述定义,
α)与式(XI)的磺酰卤反应
R5SO2-Y(XI)
其中R5为上述定义和
Y为卤素,
或
β)与式(XII)的磺酸酐在碱存在下和在稀释剂存在下反应(参见:WO 98/22438,Synthesis 1993,735及其中引证的文献)
(R5SO2)2O(XII)
其中
R5为上述定义。
式(IX-b)的内酰胺,例如可通过下述方法制备
其中R3、R4、R5、n、r和s为上述定义,
d)在氟化氢存在下和,如果需要在稀释剂(例如二氯甲烷)存在下使5-乙氧基-2-吡咯烷酮与式(XIII)的联苯类化合物反应,
其中
R3、R4、R5、r和s为上述定义。
式(X)提供了进行本发明方法(c)所需原料内酰胺的一般的定义。在上式中,R4和s各自的优选、特别优选和更特别优选定义为在对本发明式(I)化合物的说明中对这些基团作为优选、特别优选等所提及的定义。
式(X)的内酰胺是已知的和/或通过本身已知方法制备的(参见:WO 98/22438)。
式(XI)提供了进行本发明方法(c)所需原料磺酰卤的一般的定义。在上式中,R5的优选、特别优选和更特别优选定义为在对本发明式(I)化合物的说明中对于这些基团作为优选、特别优选等所提及的定义。Y优选为氟或氯。
式(XI)的磺酰卤是已知的。
式(XII)提供了进行本发明方法(c)所需原料磺酸酐的一般的定义。在上式中,R5的优选、特别优选和更特别优选定义为在对本发明式(I)化合物的说明中对于这些基团作为优选、特别优选等所提及的定义。
式(XII)的磺酸酐是已知的。
式(XIII)提供了进行本发明方法(d)所需原料联苯类化合物的一般的定义。在上式中,R3、R4、R5、r和s各自的优选、特别优选和更特别优选定义为在对本发明式(I)化合物的说明中对于这些基团作为优选、特别优选等所提及的定义。
式(XIII)的联苯类化合物是已知的。例如它们可通过下述方法制备:
e)式(XIV)的羟基联苯类化合物
其中
R3、R4、r和s为上述定义
e-1)与式(XI)的磺酰卤反应
R5SO2-Y(XI)
其中R5为上述定义和
Y为卤素,
或
e-2)与式(XII)的磺酸酐在碱(例如碳酸钾)存在下和,如果需要在稀释剂(例如乙腈)存在下反应(参见:Synthesis 1993,735以及其中所引用的文献;且参见WO 98/22438)
(R5SO2)2O(XII)
其中
R5为上述定义。
式(XIV)提供了进行本发明方法(e)所需原料羟基联苯类化合物的总的定义。在上式中,R3、R4、r和s各自的优选、特别优选和更特别优选定义为在对本发明式(I)化合物的说明中对于这些基团作为优选、特别优选等所提及的定义。
式(XIV)的羟基联苯类化合物是已知的。
进行本发明方法(A)的适合稀释剂是各种常规惰性有机溶剂。优选使用可任选卤代的脂族、脂环或芳香烃,如石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或萘烷;氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;醚,如乙醚、二异丙基醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;腈,如乙腈、丙腈、正-或异-丁腈或苯甲腈;酰胺如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-N-甲酰苯胺,N-甲基吡咯烷酮或六甲基磷酰三胺;酯如乙酸甲酯或乙酸乙酯;亚砜,如二甲基亚砜,或砜例如环丁砜。特别优选使用二氯甲烷、氯仿、甲苯、甲醇或乙醇。
适合进行本发明方法(A)的是各种常规的路易斯酸或质子酸。除去Boc的方法是一般已知的(例如参见:T.W.Greene,P.G.M.Wuts,Protective Group in Organic Synthesis,第3版,New York,Wiley&Sons,1999,pp 520-525)。优选使用三氟乙酸、HCl或HBr除去Boc保护基。
进行本发明方法(A)时,在各种情况下反应温度可在相当宽的范围内变化。通常,本方法在-20℃至+120℃,优选-10℃至60℃下进行。
当进行本发明方法(A)时,通常对每摩尔式(II)的化合物使用100摩尔的质子酸。可是,还可使用其它比例的反应成分。通过常规方法进行后处理。通常是,浓缩反应混合物,在适合的溶剂中吸收,并使用氢氧化钠调节值至pH12,用水冲洗有机相,用硫酸钠充分干燥,过滤并浓缩。如果需要可采用常规方法,如色谱分离或重结晶,从所得的残余物中分离存在的任何不纯物。
为了制备手性的式(I-c)和(I-d)化合物,可对式(IX)内酰胺进行旋光解析。例如,进行此方法时,使用制备色谱方法,优选使用高效液相色谱法(HPLC)。为此例如使用手性硅胶固定相。现已发现用N-异丁烯酰基-L-亮氨酸-D-基酰胺改性的硅胶衍生物(例如巯基丙基硅胶)特别适合分离式(IX)化合物。上述分离材料是已知的(参见:EP-A 0 379 917)。
适合的流动相是各种常规的惰性有机溶剂及其混合物。优选使用可任选卤代的脂族、脂环或芳香烃,如石油醚、己烷、庚烷、环己烷;二氯甲烷、氯仿;醇,如甲醇、乙醇、丙醇;腈,如乙腈;酯如乙酸甲酯或乙酸乙酯。特别优选使用脂族烃,如己烷或庚烷,和醇,如甲醇或丙醇,更特别优选使用正庚烷和异丙醇,或其混合物。然后将所得的(R)-构型的对映体用作上述合成途径的原料。
方法(B)
式(III)提供了进行本发明方法(B)所需原料(联)苯酚类化合物的一般的定义。在上式中,R1、R2、R3、R4、n、r和s各自的优选、特别优选和更特别优选定义为在对本发明式(I)化合物的说明中已经对于这些基团作为优选、特别优选等所提及的定义。
式(III)的(联)苯酚类化合物是已知的和/或通过本身已知方法制备的(参见:WO 98/22438)。
进行本发明方法(B)的适合的磺酰化试剂是式(XI)的磺酰卤和式(XII)的磺酸酐。
进行本发明方法(B)的适合稀释剂是各种常规惰性有机溶剂。优选使用可任选卤代的脂族、脂环或(杂)芳香烃,如石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯、吡啶或萘烷;氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;醚,如乙醚、二异丙基醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;腈,如乙腈、丙腈、正-或异-丁腈或苯甲腈;酰胺如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基N-甲酰苯胺,N-甲基吡咯烷酮或六甲基磷酰三胺;酯如乙酸甲酯或乙酸乙酯;亚砜,如二甲基亚砜,或砜例如环丁砜。特别优选使用吡啶、二氯甲烷、氯仿、四氢呋喃或甲苯。如果需要,可以使用与水的混合物并在两相系统中进行反应。
进行本发明方法(B)的适合的酸结合剂是在上述反应中的各种常规无机和有机碱。优选使用碱土金属或碱金属氢氧化物,如氢氧化钠、氢氧化钙、氢氧化钾、或氢氧化铵,碱金属碳酸盐,如碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠,碱金属或碱土金属乙酸盐,如乙酸钠、乙酸钾、乙酸钙以及叔胺,如三甲基胺、三乙基胺、三丁基胺、二乙基异丙基胺、N,N-二甲基苯胺,吡啶,N-甲基哌啶、N,N-二甲基氨基吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBN)或二氮杂二环十一烯(DBU)。特别优选使用三乙基胺、二乙基异丙基胺、氢氧化钠、氢氧化钾或碳酸钾。
进行本发明方法(B)时,反应温度可在相当宽的范围内变化。通常,反应在-70℃至+110℃,优选在-20℃至+40℃下进行。
当进行本发明方法(B)时,通常对每摩尔式(III)化合物使用1摩尔或稍过量的磺酰化试剂和0.5至3mol的酸结合剂。可是,还可使用其它比例的反应成分。通过常规方法进行后处理。通常,反应混合物被滗析、冲洗、干燥、过滤和浓缩。如果需要可采用常规方法,如色谱分离或重结晶,从所得的残余物中分离存在的任何不纯物。
方法(C)
式(IV)提供了进行本发明方法(C)所需原料吡咯啉类化合物的一般的定义。在上式中,R1、R2、R3和r各自的优选、特别优选和更特别优选定义为在对本发明式(I)化合物的说明中对于这些基团作为优选、特别优选等所提及的定义。
其中
R1、R2、R3和r各自为上述定义和
X1为氯、溴和碘。
其中
R1、R2、R3和r各自为上述定义和
X2为-OSO2CF3或-OSO2(CF2)3CF3。
式(IV-b)的吡咯啉类化合物是通过方法(A)制备的。
式(VI)提供了进行本发明方法(C)所需原料碘化物的一般的定义。在上式中,R4、R5和s各自的优选、特别优选和更特别优选定义为在对本发明式(I)化合物的说明中对于这些基团作为优选、特别优选等所提及的定义。
式(VI)的碘化物一般是已知的或市售得到。
进行根据本发明方法(C)时,经常使用钯催化剂,使用的催化剂上带有或不带有其它的配位体。优选使用的催化剂为PdCl2(dppf)[dppf=1,1’-双(二苯基膦基)二茂铁]、Pd(PPh3)4、PdCl2(PPh3)2、PdCl2(CH3CN)2、Pd2(dba)3[dba=二亚苄基丙酮]或Pd(OAc)2,特别优选PdCl2(dppf)、Pd(PPh3)4、PdCl2(PPh3)2、或Pd(OAc)2。更特别优选PdCl2(dppf)或Pd(PPh3)4。
适合的配位体是三芳基膦、三烷基膦或胂。优选使用dppf、PPh3、P(t-Bu)3、Pcy3或AsPh3,特别优选dppf。
适合的二硼酸酯为4,4,4’,4’,5,5,5’,5’-辛甲基-2,2’-双-1,3,2-二氧杂硼杂戊环、5,5,5’,5’-四甲基-2,2’-双-1,3,2-二氧杂硼杂己环、4,4,4’,4’,6,6’-六甲基-2,2’-双-1,3,2-二氧杂硼杂己环或2,2’-双-1,3,2-苯并二氧杂硼杂戊烯。所有的二硼酸酯都是已知的。
进行本发明方法(C)的适合的酸结合剂是在上述反应中的各种常规无机和有机碱。优选使用碱土金属或碱金属氢氧化物,如氢氧化钠、氢氧化钙、氢氧化钾、或氢氧化铵,碱金属碳酸盐,如碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠,碱金属或碱土金属乙酸盐,如乙酸钠、乙酸钾、乙酸钙,碱金属氟化物以及叔胺,如三甲基胺、三乙基胺、三丁基胺、N,N-二甲基苯胺,吡啶,N-甲基哌啶、N,N-二甲基氨基吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBN)或二氮杂二环十一烯(DBU)。可是,也可以在不加酸结合剂时进行反应或使用过量的胺成分,将胺同时作为酸结合剂。特别优选使用氢氧化钡、磷酸三钾、碳酸铯、碳酸钾、碳酸钠、乙酸钾、三乙基胺、叔丁醇钾(KotBu)、氟化铯或氟化钾。
进行本发明方法(C)的适合稀释剂是各种常规惰性有机溶剂。优选使用可任选卤代的脂族、脂环或芳香烃,如石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或萘烷;氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;醚,如乙醚、二异丙基醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;腈,如乙腈、丙腈,正-或异-丁腈或苯甲腈;酰胺如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基N-甲酰苯胺,N-甲基吡咯烷酮或六甲基磷酰三胺;酯如乙酸甲酯或乙酸乙酯、亚砜,如二甲基亚砜,或砜如环丁砜。特别优选使用丙酮、二甲氧基乙烷、二噁烷、四氢呋喃、二甲基甲酰胺、二甲基乙酰胺、二甲基亚砜、乙醇、甲苯或,如果需要上述稀释剂与水的混合物。
进行本发明方法(C)时,反应温度可在相当宽的范围内变化。通常,反应在0℃至140℃,优选在10℃至120℃,特别优选在20℃至120℃下进行。
可以两种不同的方式进行本发明方法(C)。在第一种方式中,式(IV)化合物先与二硼酸酯反应。然后,得到的式(V)中间体在第二步反应中与式(VI)的碘化物反应。在第二种方式中,不分离式(V)的中间体,在原位直接与式(VI)的碘化物反应。在两种不同的反应方式中,还可以最先使用式(VI)碘化物并仅在第二步中使用式(IV)的吡咯啉类化合物。
当进行本发明方法(C)时,通常对每摩尔式(IV)的化合物使用1摩尔或稍过量的二硼酸酯和1摩尔或稍过量的式(VI)碘化物以及3%的钯催化剂。可是,还可使用其它比例的反应成分。式(IV)化合物,或可选择的式(VI)化合物可以被先加入。通过常规方法进行后处理。通常,用水稀释反应混合物并用乙酸乙酯提取。用水冲洗有机相,用硫酸钠充分干燥,过滤并浓缩。如果需要可采用常规方法,如色谱分离或重结晶,从所得的残余物中分离存在的任何不纯物。为了分离式(V)中间体,在加入下步反应成分前先进行所述后处理。
本发明方法通常可在大气压力下进行。可是,在一些情况下也可在加压或减压下操作。
本发明活性化合物具有好的植物耐受性和优异的温血动物毒性,适合防治在农业、森林业、储藏产品和材料的保护,以及卫生领域中遇到的有害动物,特别是昆虫、螨类和线虫。它们优选用作作物保护剂。它们对有害动物的正常敏感和抗性品系以及对其所有或一些发育阶段都有活性。上述有害动物包括:
等足目:例如,潮虫、平甲虫和带鼠妇。
倍足目:例如,具斑马陆。
唇足目:例如,食果地蜈蚣和蚰蜒。
综合目:例如,庭园么蚰。
缨尾目:例如,西洋衣鱼。
弹尾目:例如,具刺跳虫。
直翅目:家蟋蟀、蝼蛄属、热带飞蝗、黑蝗属和沙漠蝗。
蜚蠊目:例如,东方蜚蠊、美洲大蠊、马得拉蜚蠊和德国小蠊、
革翅目:例如,欧洲球螋。
等翅目:例如,散白蚁属。
虱目:例如,头虱、血虱属、颚虱属、嚼虱属和畜虱属。
缨翅目:例如温室条蓟马、烟蓟马、蓟马(Thrips palmi)和苜蓿蓟马。
半翅目:例如,褐盾蝽、棉红蝽、甜菜拟网蝽、臭虫、长红蜡蝽和吸血猎蝽。
同翅目:例如,甘蓝粉虱、棉粉虱、温室白粉虱、棉蚜、甘蓝蚜、茶鹿隐瘤额蚜、豆蚜、苹果蚜、苹果绵蚜、桃大尾蚜、根瘤蚜、瘿绵蚜属、麦长管蚜、桃蚜属、忽布瘤额蚜、粟缢管蚜、叶蝉属、纹叶蝉、黑尾叶蝉、李蜡蚧、揽珠蜡蚧、灰飞虱、褐飞虱、红圆蚧、春藤园盾蚧、粉蚧属和木虱属。
鳞翅目:例如,红铃虫、松天蛾、冬天蛾、苹果细蛾、苹果巢蛾、小菜蛾、黄褐天幕毛虫、黄毒蛾、毒蛾属、棉潜叶蛾、桔潜叶蛾、地老虎属、切根虫属、褐夜蛾、实夜蛾属、棉铃虫属、甜菜夜蛾、甘蓝夜蛾、小眼夜蛾、斜纹夜蛾、粘虫属、粉纹夜蛾、苹果蠹蛾、粉蝶属、螟属、玉米螟、地中海粉螟、大蜡螟、负袋衣蛾、织网衣蛾、褐织夜蛾、亚麻黄卷蛾、烟卷蛾、云杉卷夜蛾、葡萄果蠹蛾、茶长卷夜蛾和栎纵卷夜蛾。
鞘翅目:例如,具斑窃蠹、谷蠹、豆象、大豆象、家天牛、萤叶甲、马铃薯甲虫、蜡根猿叶甲、条叶甲属、油菜跳甲、墨西哥豆瓢虫、隐金甲属、锯谷盗、花象甲属、谷象属、葡萄黑耳喙象、香蕉根叶甲、甘蓝荚象甲、苜蓿叶象甲、皮蠹属、斑皮蠹属、圆皮蠹、黑毛皮蠹、粉蠹属、油菜花露尾甲、蛛甲属、金黄蛛甲、麦蛛甲、拟谷盗属、黄粉甲、叩甲属、金针虫属、金龟、六月金龟、新西兰肋翅鳃角金龟、美洲稻象甲。
膜翅目:例如,松叶蜂、叶蜂属、蚁属、厨蚁和胡蜂属。
双翅目:例如,伊蚊属、按蚊属、库蚊属、黄猩猩果蝇、家蝇属、厩蝇属、红头丽蝇、绿蝇属、金蝇属、疽蝇属、胃蝇属、虱蝇属、螫蝇属、鼻蝇属、皮蝇属、虻属、螗蜩、花园毛蚊、瑞典麦杆蝇、草种蝇属、甜菜潜叶蝇、地中海实蝇、油橄榄实蝇、和欧洲大蚊、种蝇属和斑潜蝇属。
蚤目:例如,东方鼠蚤和蚤。
蜱螨目:例如,蝎(Scorpio maurus)、红蜘蛛、粗脚粉螨、锐缘蜱属、钝缘蜱属、鸡皮刺螨、兔瘿螨、桔锈螨、牛蜱属、头蜱属、花蜱属、璃眼蜱属、硬蜱属、痒螨属、皮痒螨属、疥螨属、附线螨属、苜蓿苔属螨、全爪螨属、红叶螨属、半跗线螨属和短须螨属。
对植物有害的的线虫包括例如短体线虫属、相似穿孔线虫、起绒草茎线虫、羊穿刺线虫、异皮线虫属、球异皮线虫属、根节线虫属、滑刃线虫属、长针线虫属、剑线虫属、毛刺线虫属和伞滑刃线虫属。
根据本发明的式(I)化合物对鳞翅目幼虫、甲虫幼虫、蜘蛛、蚜虫和潜叶蝇表现出非常好的活性。
如果需要,根据本发明的化合物在一定浓度或施用剂量下,还可以用作除草剂和杀微生物剂,例如杀真菌剂、防霉剂和杀细菌剂。如果需要,它们还可用作合成其它活性化合物的中间体或前体。
根据本发明可以处理所有植物和部分植物。在本文中对植物可理解为所有植物和植物群落,如有用和有害的野生植物或作物(包括天然生长的作物)。被种植的作物可以通过常规的植物种植和最佳的方法、或通过生物技术和基因工程方法或通过上述方法的组合方法获得,作物包括转基因植物并包括受种植者权益保护或不保护的植物品种。植物部分可被理解为植物全部的地上和地下部分和器官,如茎枝、叶、花和根,例如可被述及的是:叶、针叶、茎、茎干、花、子实体、果实、种子、根、块茎和根茎。植物部分还包括收获的物质和植物和植物繁殖材料,例如插枝、块茎、根茎、侧枝和种子。
根据本发明可用活性化合物处理植物和植物部分,可使用常规的处理方法使植物直接接触活性化合物或使化合物与植物周围、环境或储藏地接触,常规方法例如浸渍、喷雾、蒸发、雾化、分散、涂布,在对植物繁殖材料、特别是种子处理时还可一层或多层包衣。
本活性化合物可被制备成为常规的制剂,如液剂,乳剂,可湿性粉剂,悬浮剂,粉剂,细粉剂,糊剂、可溶粉剂,颗粒剂,浓悬浮乳剂,用活性化合物浸渍的天然和合成材料,在聚合物中的微细胶囊。
这些制剂是以已知方法生产的,例如,通过将本发明活性成分与填充剂,即液体溶剂和/或固体载体混合而生产,制剂中可选择的可使用表面活性剂,即乳化剂和/或分散剂,和/或成泡剂。
在使用水作为填充剂的情况下,例如,也可使用有机溶剂作为助溶剂。适当的液体溶剂主要有:芳香烃类,如二甲苯、甲苯或烷基萘,氯代芳烃类或氯代脂族烃类如氯苯、二氯乙烷或二氯甲烷,脂族烃类,如环己烷或烷属烃,例如矿物油馏份,矿物油和植物油,醇类,如丁醇或乙二醇及其醚和酯类,酮类,如丙酮,甲基乙基酮,甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺和二甲基亚砜,以及水。
适合的固体载体有:
例如,铵盐和天然矿物粉末,如高岭土,粘土,滑石,白垩,石英,硅镁土,蒙脱土或硅藻土,和合成矿物粉末,如细分散二氧化硅,氧化铝和硅酸盐;适合颗粒剂的固体载体有:例如,粉碎和分级的天然岩石,如方解石,大理石,浮石,海泡石和白云石,以及无机和有机粉末的合成颗粒,和有机材料的颗粒如锯末,坚果壳,玉米穗茎和烟草茎;
适合的乳化剂和/或成泡剂有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯,聚氧乙烯脂肪醇醚,例如烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基硫酸盐以及蛋白水解产物;
适合的分散剂有:例如木质素亚磺酸废液和甲基纤维素。
在制剂中还可使用粘合剂如羧甲基纤维素天然和合成粉末、颗粒或胶乳状合成聚合物,如阿拉伯树胶,聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂如脑磷脂和卵磷脂,和合成磷脂。其它的粘合剂可以是矿物油和植物油。
可能使用的着色剂如无机颜料,例如氧化铁,氧化钛和普鲁士兰,和有机染料,如茜素染料,偶氮染料和金属酞菁染料,和痕量营养物如金属盐,例如,铁、锰、硼、铜、钴、钼和锌盐。
制剂中通常含有按重量计0.1%-95%,优选按重量计0.5%-90%的活性化合物。
根据本发明的活性化合物可以就这样或以其制剂以及与其它已知活性化合物的混合物的形式存在,其它活性化合物如杀虫剂、引诱剂、消毒剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、植物生长调节剂或除草剂,例如,在制剂中包括已知的活性化合物是为了扩大活性作用谱或防止抗性的发展。在许多情况下,可以获得增效作用,即,混合物的活性大于单独成分的活性。例如,杀虫剂包括:磷酸酯、氨基甲酸酯、羧酸酯、卤代烃类、苯基脲类和从微生物中生产的物质等。
在混合物中适合的混用成分为下述化合物:
杀真菌剂:
aldimorph、氨丙膦酸、氨丙膦酸钾盐、andoprim、敌菌灵、氧环唑、腈嘧菌酯,
苯霜灵、麦锈灵、苯菌灵、苄烯酸、苄烯酸异丁酯、双丙氨膦、乐杀螨、联苯、联苯三唑醇、灭瘟素、糠菌唑、乙嘧酚磺酸酯、丁硫啶,
石硫合剂、capsimycin、敌菌丹、克菌丹、多菌灵、萎锈灵、carvon、灭螨猛、灭瘟唑、苯咪唑菌、地茂散、氯化苦、百菌清、乙菌利、clozylacon、硫杂灵、霜脲氰、环丙唑醇、嘧菌环胺、酯菌胺,
咪菌威、双氯酚、苄氯三唑醇、diclofluanid、哒菌酮、氯硝胺、乙霉威、苯醚甲环唑、二甲嘧酚、烯酰吗啉、烯唑醇、烯唑醇-M、敌螨普、二苯胺、吡菌硫、灭菌磷、二氰蒽醌、十二环吗啉、多果定、敌菌酮,
敌瘟磷、氧唑菌、乙环唑、乙嘧酚、土菌灵,
噁唑酮菌、咪菌腈、氯苯嘧啶醇、腈苯唑、呋菌胺、种衣酯、拌种咯、苯锈啶、丁苯吗啉、醋酸三苯基锡、羟基三苯锡、福美铁、嘧菌腙、氟啶胺、氟联苯菌、氟氯菌核利、氟喹唑、呋嘧醇、氟硅唑、磺菌胺、氟酰胺、粉唑醇、灭菌丹、三乙膦酸铝、三乙膦酸钠、四氯苯酞、麦穗宁、呋霜灵、呋吡唑灵、灭菌胺、呋菌唑、呋醚唑、拌种胺,
双胍盐,
六氯苯、己唑醇、噁霉灵,
抑霉唑、亚胺唑、双胍辛、双八胍盐、双胍辛醋酸盐、iodocarb、种菌唑、异稻瘟净(IBP)、异菌脲、irumamycin、稻瘟灵、氯苯咪菌酮,
春雷霉素、亚胺菌、含铜制剂如:氢氧化铜、环烷酸铜、王铜、硫酸铜、氧化铜、喹啉酮和波尔多液,
代森锰铜、代森锰锌、代森锰、meferimzone、嘧菌胺、灭锈胺、甲霜灵、叶菌唑、磺菌威、呋菌胺、代森联、苯吡咯菌、噻菌胺、米多霉素、腈菌唑、甲菌利,
福美镍、异丙消、氟苯嘧啶醇,
呋酰胺、噁霜灵、oxamocarb、喹菌酮、氧化萎锈灵、oxyfenthiin,
多效唑、稻瘟酯、戊菌唑、戊菌隆、氯瘟磷、picoxystrobin、多马霉素、哌丙灵、多抗霉素、polyoxorim、烯丙苯噻唑、咪鲜胺、腐霉利、霜霉威、propanosine-sodium、丙环唑、丙森锌、pyraclostrobin、吡菌磷、啶斑肟、嘧霉胺、咯喹酮、氯吡呋醚,
唑喹菌酮、五氯硝基苯(PCNB),
硫磺粉和硫制剂,
戊唑醇、叶枯酞、四氯硝基苯、四环唑、四氟醚唑、噻菌灵、噻菌腈、溴氟唑菌、甲基硫菌灵、福美双、硫氰苯甲酰胺、甲基立枯磷、甲苯氟磺胺、三唑酮、三唑醇、叶锈特、咪唑嗪、水杨菌胺、三环唑、十三吗啉、trifloxystrobin、氟菌唑、嗪胺灵、灭菌唑,
烯效唑,
有效霉素、乙烯菌核利、烯霜苄唑,
氰菌胺、代森锌、福美锌以及
咪草酸,OK-8705,OK-8801,
α-(1,1-二甲基乙基)-β-(2-苯氧基乙基)-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-氟-b-丙基-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-甲氧基-α-甲基-1H-1,2,4-三唑-1-乙醇,
α-(5-甲基-1,3-二噁烷-5-基)-β-[[4-(三氟甲基)-苯基]-亚甲基]-1H-1,2,4-三唑-1-乙醇,
(5RS,6RS)-6-羟基-2,2,7,7-四甲基-5-(1H-1,2,4-三唑-1-基)-3-辛酮,
(E)-α-(甲氧基亚氨基)-N-甲基-2-苯氧基-苯乙酰胺,
{2-甲基-1-[[[1-(4-甲基苯基)乙基]氨基]羰基]丙基}-氨基甲酸-1-异丙基酯,
1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)-乙酮-O-(苯基甲基)肟,
1-(2-甲基-1-萘基)-1H-吡咯-2,5-二酮,
1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯烷二酮,
1-[(二碘甲基)-磺酰基]-4-甲基苯,
1-[[2-(2,4-二氯苯基)-1,3-二氧戊环-2-基]-甲基]-1H-咪唑,
1-[[2-(4-氯苯基)-3-苯基环氧乙烷基]-甲基]-1H-1,2,4-三唑,
1-[1-[2-[(2,4-二氯苯基)-甲氧基]-苯基]-乙烯基]-1H-咪唑,
1-甲基-5-壬基-2-(苯基甲基)-3-吡咯烷醇,
2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟-甲基-1,3-噻唑-5-甲酰苯胺,
2,2-二氯-N-[1-(4-氯苯基)-乙基]-1-乙基-3-甲基环丙烷甲酰胺,
2,6-二氯-5-(甲硫基)-4-嘧啶基硫氰酸酯,
2,6-二氯-N-(4-三氟甲基苄基)苯甲酰胺,
2,6-二氯-N-[[4-(三氟甲基)-苯基]-甲基]-苯甲酰胺,
2-(2,3,3-三碘-2-丙烯基)-2H-四唑,
2-[(1-甲基乙基)-磺酰基]-5-(三氯甲基)-1,3,4-噻二唑,
2-[[6-脱氧-4-O-(4-O-甲基-β-D-吡喃葡萄糖基)-α-D-吡喃葡萄糖基]-氨基]-4-甲氧基-1H-吡咯并[2,3-d]嘧啶-5-腈,
2-氨基丁烷,
2-溴-2-(溴甲基)-戊二腈,
2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺,
2-氯-N-(2,6-二甲基苯基)-N-(异硫氰酸根合甲基)-乙酰胺,
2-苯基苯酚(OPP),
3,4-二氯-1-[4-(二氟甲氧基)-苯基]-1H-吡咯-2,5-二酮,
3,5-二氯-N-[氰基[(1-甲基-2-丙炔基)-氧基]-甲基]-苯甲酰胺,
3-(1,1-二甲基丙基)-1-氧代-1H-茚-2-腈,
3-[2-(4-氯苯基)-5-乙氧基-3-异噁唑烷基]-吡啶,
4-氯-2-氰基-N,N-二甲基-5-(4-甲基苯基)-1H-咪唑-1-磺酰胺,
4-甲基-四唑并[1,5-a]喹唑啉-5(4H)-酮,
8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二噁螺[4.5]癸烷-2-甲胺,
8-羟基喹啉硫酸盐,
9H-呫吨-9-羧酸-2-[(苯基氨基)-羰基]-酰肼,
双-(1-甲基乙基)-3-甲基-4-[(3-甲基苯甲酰基)-氧基]-2,5-噻吩二羧酸酯,
顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇,
顺-4-[3-[4-(1,1-二甲基丙基)-苯基-2-甲基丙基]-2,6-二甲基-吗啉盐酸盐,
[(4-氯苯基)-偶氮]-氰基乙酸乙基酯,
碳酸氢钾,
甲基四硫醇钠盐,
1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯,
N-(2,6-二甲基苯基)-N-(5-异噁唑基羰基)-DL-氨基丙酸甲酯,
N-(氯乙酰基)-N-(2,6-二甲基苯基)-DL-氨基丙酸甲酯,
N-(2,3-二氯-4-羟基苯基)-1-甲基环己烷甲酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-呋喃基)-乙酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-噻吩基)-乙酰胺,
N-(2-氯-4-硝基苯基)-4-甲基-3-硝基-苯磺酰胺,
N-(4-环己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(4-己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(5-氯-2-甲基苯基)-2-甲氧基-N-(2-氧代-3-噁唑烷基)-乙酰胺,
N-(6-甲氧基-3-吡啶基)-环丙烷甲酰胺,
N-[2,2,2-三氯-1-[(氯乙酰基)-氨基]-乙基]-苯甲酰胺,
N-[3-氯-4,5-双-(2-丙炔氧基)-苯基]-N’-甲氧基-甲基亚氨酸酰胺(methanimidamid),
N-甲酰基-N-羟基-DL-氨基丙酸钠,
[2-(二丙基氨基)-2-氧代乙基]-乙基硫代氨基磷酸O,O-二乙酯,
苯基丙基硫代氨基磷酸O-甲基S-苯基酯,
1,2,3-苯并噻二唑-7-硫代羧酸S-甲酯,
螺[2H]-1-苯并吡喃-2,1’(3’H)-异苯并呋喃]-3’-酮,
4-[3,4-(二甲氧苯基)-3-(4-氟苯基)丙烯酰基]吗啉
杀细菌剂:
溴硝丙二醇、双氯酚、三氯甲基吡啶、福美镍、春雷霉素、辛噻酮、呋喃羧酸、土霉素、烯丙苯噻唑、链霉素、叶枯酞、硫酸铜和其它铜制剂。
杀虫剂/杀螨剂/杀线虫剂:
阿维菌素、乙酰甲胺磷、啶虫脒、氟丙菊酯、棉铃威、涕灭威、砜灭威、顺式氯氰菊酯、甲体氯氰菊酯、双甲脒、齐墩螨素、AZ 60541、艾扎丁、甲基吡恶磷、谷硫磷A、谷硫磷M、三唑锡,
日本甲虫芽孢杆菌、球形芽孢杆菌、枯草芽孢杆菌、苏云金杆菌、baculoviruses、蚕白僵菌、纤细白僵菌、噁虫威、丙硫克百威、杀虫磺、苯螨特、高效氟氯氰菊酯、联苯肼酯、联苯菊酯、bioethanomethrin、生物氯菊酯、bistrifluron、仲丁威、溴硫磷A、合杀威、噻嗪酮、特嘧硫磷、丁酮威、丁基哒螨灵,
硫线磷、甲萘威、克百威、三硫磷、丁硫克百威、杀螟丹、chloethocarb、氯氧磷、氟唑虫清、毒虫畏、氟啶脲、氯甲磷、毒死蜱、甲基毒死蜱、chlovaporthrin、chromafenozide、顺式苄呋菊酯、顺式氯菊酯、clocythrin、除线威、四螨嗪、clothianidine、杀螟腈、cycloprene、乙氰菊酯、氟氯氰菊酯、氯氟氰菊酯、三环锡、氯氰菊酯、灭蝇胺,
溴氰菊酯、甲基内吸磷、内吸磷硫赶式异构体、甲基内吸磷硫赶式异构体、丁醚脲、二嗪磷、敌敌畏、三氯杀螨醇、除虫脲、乐果、甲基毒虫畏、苯虫醚、乙拌磷、碘酰丁二辛、苯氧炔螨,
eflusilanate、emamectin、右旋烯炔菊酯、硫丹、虫霉属、S-氰戊聚酯、乙硫苯威、乙硫磷、灭线磷、醚菊酯、特苯噁唑、乙嘧硫磷,
苯线磷、喹螨醚、苯丁锡、杀螟硫磷、苯硫威、fenoxacrim、苯氧威、甲氰菊酯、fenpyrad、fenpyrithrin、唑螨酯、氰戊菊酯、氟虫腈、氟啶胺、啶蜱脲、溴氟菊酯、氟环脲、氟氰戊菊酯、氟虫脲、氟氯苯菊酯、flutenzine、氟胺氰菊酯、地虫硫磷、丁苯硫磷、噻唑磷、fubfenprox、呋线威,
颗粒体病毒,
特丁苯酰肼、六六六、庚烯磷、氟铃脲、噻螨酮、烯虫乙酯,
吡虫啉、噁二唑虫、氯唑磷、异柳磷、噁唑磷、齐墩螨素,
核多角体病毒,
高效氯氟氰菊酯、氟丙氧脲,
马拉硫磷、灭蚜磷、四聚乙醛、甲胺磷、Metharhiziumanisopliae、Metharhizium flavoviride、杀扑磷、甲硫威、烯虫酯、灭多威、甲氧苯酰肼、速灭威、噁虫酮、速灭磷、米尔螨素、milbemycin、久效磷,
二溴磷、烯啶虫胺、硝虫噻嗪、双苯氟脲,
氧乐果、杀线威、亚砜磷,
玫烟色拟青霉、对硫磷A、甲基对硫磷、氯菊酯、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、辛硫磷、抗蚜威、嘧啶磷A、甲基嘧啶磷、丙溴磷、猛杀威、克螨特、残杀威、丙硫磷、发硫磷、吡蚜酮、吡唑硫磷、反灭虫菊、除虫菊素、哒螨灵、pyridathion、嘧螨醚、吡丙醚,
喹硫磷,
ribavirin,
杀抗松、硫线磷、氟硅菊酯、艾克敌105、spirodiclofen、sulfotep、硫丙磷,
氟胺氰菊酯、虫酰肼、吡螨胺、嘧丙磷、氟苯脲、七氟菊酯、双硫磷、灭虫畏、特丁硫磷、杀虫畏、三氯杀螨砜、辛体氯氰菊酯、thiacloprid、thiamethoxam、噻丙腈、thiatriphos、硫环杀、硫双威、久效威、敌贝特、溴氯氰菊酯、四溴菊酯、苯螨噻、唑蚜威、三唑磷、triazuron、氯咪唑、敌百虫、杀铃脲、混杀威,
蚜灭多、氟吡唑虫、麦柯特尔,
YI 5302,
己体氯氰菊酯、zolaprofos,
(1R-顺)-[5-(苯基甲基)-3-呋喃基]-甲基3-[(二氢-2-氧代-3(2H)-亚呋喃基)-甲基]-2,2-二甲基环丙烷羧酸酯,
(3-苯氧基苯基)-甲基2,2,3,3-四甲基环丙烷羧酸酯,
1-[(2-氯-5-噻唑基)甲基]四氢-3,5-二甲基-N-硝基-1,3,5-三嗪-2(1H)-亚胺,
2-(2-氯-6-氟苯基)-4-[4-(1,1-二甲基乙基)苯基]-4,5-二氢-噁唑,
2-(乙酰氧基)-3-十二烷基-1,4-萘二酮,
2-氯-N-[[[4-(1-苯基乙氧基)-苯基]-氨基]-羰基]-苯甲酰胺,
2-氯-N-[[[4-(2,2-二氯-1,1-二氟乙氧基)-苯基]-氨基]-羰基]-苯甲酰胺,
3-甲基苯基丙基氨基甲酸酯,
4-[4-(4-乙氧基苯基)-4-甲基戊基]-1-氟-2-苯氧基-苯,
4-氯-2-(1,1-二甲基乙基)-5-[[2-(2,6-二甲基-4-苯氧基苯氧基)乙基]硫代]-3(2H)-哒嗪酮,
4-氯-2-(2-氯-2-甲基丙基)-5-[(6-碘-3-吡啶基)甲氧基]-3(2H)-哒嗪酮,
4-氯-5-[(6-氯-3-吡啶基)甲氧基]-2-(3,4-二氯苯基)-3(2H)-哒嗪酮,
苏云金芽孢杆菌EG-2348株系,
苯甲酸[2-苯甲酰基-1-(1,1-二甲基乙基)]-酰肼,
丁酸2,2-二甲基-3-(2,4-二氯苯基)-2-氧代-1-氧杂螺[4,5]癸-3-烯-4-基酯,
[3-[(6-氯-3-吡啶基)甲基]-2-亚噻唑烷基]-氨腈,
二氢-2-(硝基亚甲基)-2H-1,3-噻嗪-3(4H)-甲醛,
[2-[[1,6-二氢-6-氧代-1-(苯基甲基)-4-哒嗪基]氧基]乙基]-氨基甲酸乙酯,
N-(3,4,4-三氟-1-氧代-3-丁烯基)-甘氨酸,
N-(4-氯苯基)-3-[4-(二氟甲氧基)苯基]-4,5-二氢-4-苯基-1H-吡唑-1-甲酰胺,
N-[(2-氯-5-噻唑基)甲基]-N’-甲基-N”-硝基-胍,
N-甲基-N’-(1-甲基-2-丙烯基)-1,2-肼硫代二甲酰胺
N-甲基-N’-2-丙烯基-1,2-肼硫代二甲酰胺,
[2-(二丙基氨基)-2-氧代乙基]-乙基硫代氨基磷酸(phosphoramidothioat)O,O-二乙酯,
N-氰甲基-4-三氟甲基-烟酰胺,
3,5-二氯-1-(3,3-二氯-2-丙烯氧基)-4-[3-(5-三氟甲基吡啶-2-基氧基)丙氧基]-苯。
还可以是与其它已知活性化合物,如除草剂、或与肥料和生长调节剂的混合物。
根据本发明的活性化合物可以其市售制剂和从上述制剂制备的应用形式,以及与增效剂的混合物的形式存在。增效剂是能够增加本发明活性化合物活性的化合物,但加入的增效剂本身不需要有活性。
从市售制剂制备的应用形式中活性化合物的含量可在很宽的范围内变化。使用形式中活性化合物的浓度可以为0.0000001至95%重量的活性化合物,优选0.0001至1%重量。
本化合物以适用于使用形式的常规方法进行使用。
当用来防治卫生害虫和储藏产品害虫时,活性化合物对木材和粘土具有非常好的残留活性,并对石灰物质的碱性存在好的稳定性。
如上所述,根据本发明可以处理所有植物和植物部分。在优选的实施方案中,可以处理野生植物种类和植物品种、或通过常规生物培养的方法,如杂交或原生质体融合制备的植物及其部分。更优选的实施方案中,可处理通过基因工程,如果需要与常规方法组合(GeneticModified Organisms)获得的转基因植物和植物品种及其部分。术语“部分”或“植物的部分”或“植物部分”如上所述。
特别优选地,根据本发明可处理各自可从市场上购买或正在应用的植物品种的植株。植物品种应理解为通过常规栽培、通过诱变或通过DNA重组技术获得的具有某些品质的植物。它们可以是品种、生物-和基因型。
根据植物种类或植物品种,其生长地和生长条件(土壤、气候、种植期、营养)还可通过本发明处理获得超过加和(“增效”)作用。因此,例如,降低使用量和/或增加活性谱和/或增加本发明中使用的物质和组合物的活性,使植物更好的生长、增加对高或低温的耐受性、增加对干旱或对水或对土壤盐含量的耐受性、增加开花的质量、更容易收获、加速成熟、较高产量、收获产品的较好品质和/或较高的营养价值、较好的储藏稳定性和/或收获产品的可加工性,可能超过实际所预期的效果。
根据本发明优选被处理的转基因植物或植物品种(即通过基因工程方法制备的植物)包括所有植物,括基因改性中上述植物获得了给予它们特别有益品质的基因材料。上述品质的实例为使植物更好的生长、增加对高或低温的耐受性、增加对干旱或对水或对土壤盐含量的耐受性、增加开花的质量、更容易收获、加速成熟、较高产量、收获产品的较好品质和/或较高的营养价值、较好的储藏稳定性和/或收获产品的可加工性。进一步和应特别强调的上述品质的实例是较好地保护植物不受有害动物和微生物,如昆虫、螨、致病真菌、细菌和/或病毒的侵害,且还可增加植物对一些除草活性化合物的耐受性。上述转基因植物的实例为重要的作物,如谷类(小麦、水稻)、玉米、大豆、马铃薯、棉花、菜籽油菜以及果树植物(苹果、梨、柑桔和葡萄)、且特别应强调的是玉米、大豆、马铃薯、棉花和菜籽油菜。应特别强调的品质是在植物中增加保护植物不受昆虫侵害的毒素的形成,特别是在植物中形成从苏云菌芽孢杆菌基因材料(例如基因CryIA(a)、CryIA(b)、CryIA(c)、CryIIA、CryIIIA、CryIIIB2、Cry9c、Cry2Ab、Cry3Bb和CryIF及其组合)中获得的毒素(本文中称作“Bt”植物)。应更特别强调的品质是通过获得系统抗性(SAR)、系统毒素、植物抗毒素、引导物和抗性基因、和表达的相应蛋白质和毒素,增加植物对真菌、细菌和病毒的抗性。应更特别强调的品质是增加植物对一些除草剂活性化合物,例如咪唑啉酮类、磺酰脲类、草甘膦或Phosphinotricin(例如“PAT”基因)的耐受性。在转基因植物中,具有上述的有益品质基因,还可以以彼此组合的形式存在。上述“Bt”植物的实例为以下述商品名销售的玉米品种、棉花品种、大豆品种和马铃薯品种,YIELD GARD(例如玉米、棉花、大豆)、KnockOut(例如玉米)、StarLink(例如玉米)、Bollgard(棉花)、Nucotn(棉花)和NewLeaf(马铃薯)。上述耐除草剂植物的实例为以下述商品名销售的玉米品种、棉花品种和大豆品种,Roundup Ready(例如耐草甘膦的玉米、棉花、大豆)、Liberty Link(例如耐phosphinotricin的菜籽油菜)、IMI(耐咪唑啉酮)和STS(例如耐磺酰脲的玉米)。上述抗除草剂植物(以常规方式培养的耐除草剂植物)包括以商品名Clearfield(例如玉米)销售的品种。当然,上述说明还适用于具有上述或正培育的基因品质的植物品种,在将来这些植物将被培育或市场化。
根据本发明可以特别优选的方式用本发明通式(I)的化合物或本发明活性化合物的混合物处理上述例示的植物。上述活性化合物或混合物的优选范围也适用于处理这些植物。特别应强调的是用本文中特别述及的化合物或混合物处理植物。
根据本发明的活性化合物不仅对植物害虫、卫生领域害虫和储藏产品害虫具有活性,而且在兽医领域,对防治动物寄生虫(外寄生虫)也有活性,例如硬蜱、软蜱、疥螨、叶螨、蝇(叮咬和吸食)、寄生性蝇幼虫、虱目、头虱、鸟虱和蚤。上述寄生虫包括:
虱目例如:血虱属、颚虱属、虱属、阴虱属和管虱属。
食毛目和粗颈豆象亚目和细角亚目,例如:毛羽虱属、短角鸟虱属、巨羽虱属、牛羽虱属、Werneckiella spp.Lepikentron spp.、畜虱属、嚼虱属和猫羽虱属。
双翅目和长角亚目和短角亚目例如,伊蚊属、按蚊属、库蚊属、蚋属、真蚋属、白蛉属、Lutzomyia spp、库蠓属、斑虻属、瘤虻属、黄蠓属、虻属、麻虻属、Philipomyia spp.、Braula属、(家)蝇属、Hydrotaea属、螫蝇属、血蝇属、蜂虱蝇属、厕蝇属、舌蝇属、丽蝇属、绿蝇属、金蝇属、肉蝇属、麻蝇属、狂蝇属、皮蝇属、胃蝇属、虱蝇属、食毛属和蜱蝇属。
蚤目,例如蚤属、栉首蚤属、客蚤属和角叶蚤属。
异翅亚目,例如臭虫属、椎猎椿属、猎椿属和全园蝽属。
蜚蠊目,例如东方蜚蠊、美洲大蠊、德国小蠊和带蠊属。
蜱螨亚纲和后-和中气门亚目,例如锐缘蜱属、钝缘蜱属、残喙蜱属、硬蜱属、花蜱属、牛蜱属、革蜱属、血蜱属、璃眼蜱属、扇头蜱属、革蜱属、刺利螨属、肺刺螨属、胸口螨属和瓦螨属。
辐螨亚目(前气门亚目)和粉螨亚目(无气门亚目),例如蜂跗线螨、姬螫螨属、禽螫螨属、肉螨属、疮螨属、蠕形螨属、恙螨属、牦螨属、粉螨属、食酪螨属、嗜木螨属、颈下螨属、翅螨属、瘙螨属、痒螨属、耳螨属、疥螨属、痂螨属、疙螨属、胞螨属和皮膜螨属。
例如它们还对发育阶段的蜱,例如花蜱(Amblyomma hebraeum〕,和寄生蝇,例如铜绿蝇表现出非常突出的活性。
根据本发明使用的式(I)活性化合物也适用于防治侵扰农业家畜的节肢动物,农业家畜如牛、绵羊、山羊、马、猪、驴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅和蜜蜂,其它家养动物,例如狗、猫、笼养鸟和水族馆的鱼,还有所谓的试验动物,例如田鼠、豚鼠、大鼠和小鼠。通过防治上述节肢动物,旨在减少动物死亡和减产(肉、奶、毛、皮、蛋、蜜等),因此,通过使用本发明的活性化合物,可以使畜牧业更经济、更简单。
在兽医部门,本发明的活性化合物可用已知方法给药,即经肠给药,例如以片剂、胶囊剂、饮剂、灌药剂、颗粒剂、膏剂、大丸剂、饲养过程和栓剂等形式进行;非经肠给药(肌肉注射、皮下注射、静脉注射、腹膜内注射等)、植入法;经鼻给药;经皮给药,例如以浸泡或洗浴、喷雾、泼上或擦上、洗涤和撒粉形式进行,也可借助于含有活性化合物的成型制品进行,例如项圈、耳饰物、尾饰物、肢环(带)、笼头、装饰器具等。
当本发明式(I)的活性化合物用于牛、家禽、宠物等时,它们可以含有1至80%重量本发明活性化合物的制剂(例如粉剂、乳液、自由流动组合物)直接使用,或稀释100至10,000倍后使用,或将其以化学浴形式使用。
进一步地还发现,本发明化合物对储藏工业品中的昆虫具有极强的杀虫活性。
可提及的非限定性地优选实例为下述昆虫:
甲虫,例如:
北美家天牛、绿虎天牛(Chlorophorus pilosis)、家具窃蠹、报死材窃蠹、翼窃蠹(Ptilinus pecticornis)、松长蠹(dendrobiumpertinex)、松芽枝窃蠹、窃蠹(Priobium carpini)、褐粉蠹、美洲粉蠹、南方粉蠹、栎粉蠹、粉蠹(Lyctus pubescens)、胸粉蠹(Trogoxylon aequale)、鳞毛粉蠹、材小蠹、Tryptodendron spec.、咖啡黑长蠹、长蠹、褐异翅长蠹和棘长蠹、竹竿粉长蠹。
膜翅目,例如:
黑足树蜂、云杉大树蜂、泰加大树蜂和大树蜂(Urocerus augur)。
白蚁,例如:
木白蚁(Kalotermes flavicollis)、麻头堆白蚁、印巴结构木白蚁、欧美散白蚁、散白蚁Reticulitermes santonensis、Reticulitermes lucifugus、达尔文澳白蚁、内华达古白蚁和台湾乳白蚁。
衣鱼,如台湾衣鱼。
在本申请中工业材料意为无活性材料,优选例如塑料、粘合剂、胶料、纸和纸板、皮革、木材和加工木制品和涂层组合物。
木材和加工木制品作为被保护的材料,特别优选的是防止昆虫侵染。
被本发明制剂和含有其的混合物保护的木材和加工木制品的定义例如:
建筑木材、木梁、铁路枕木、桥梁、船帮、木车、箱子、托台、容器、电话孔、镶板、木窗和门、夹板、硬纸板、通常用于室内和建筑品中的家具或木制品。
本活性化合物可以其浓缩物形式或常规的制剂形式使用,制剂形式如粉剂、颗粒剂、液剂、悬浮剂、溶剂或糊剂。
上述制剂可通过现有技术中的已知方法制备,例如通过将本发明活性成分与至少一种溶剂或稀释剂、乳化剂、分散剂和/或粘合剂或固定剂、防水剂混合,如果需要可加入催干剂和UV稳定剂和如果需要可加入染料和颜料,以及其它加工助剂。
用于木材和木材制备的木制品保护中的杀虫组合物或浓缩物中含有浓度为0.0001至95%重量,优选0.001至60%重量的本发明活性成分。
组合物或浓缩物的使用量是根据昆虫的性质和发生期以及存在的介质而确定的。最佳的使用量可根据一系列试验确定。可是,通常以被保护的材料为基础,活性化合物的使用量为0.0001至20%重量,优选0.001至10%重量则足够了。
使用的溶剂和/或稀释剂为有机的化学溶剂或溶剂混合物和/或油或油状低挥发性的有机化学溶剂或溶剂混合物和/或极性有机化学溶剂或溶剂混合物和/或水,且如果需要包含乳化剂和/或湿润剂。
优选使用的有机化学溶剂是蒸发系数大于35和闪点大于30℃,优选大于45℃的油或油状溶剂。用作低挥发性油或油状的水不溶溶剂的物质是适合的矿物油或其芳香馏份,或含有矿物油的溶剂混合物,优选石油溶剂、石油和/或烷基苯。
优选使用沸点范围170至220℃的矿物油,沸点范围170至220℃的石油溶剂,沸点范围250至350℃的锭子油,沸点160至280℃的石油或芳烃,萜品油等。
在优选的实施方案中使用沸点范围180至210℃的液体脂族烃,或沸点范围180至220℃的高沸点芳烃和脂族烃混合物和/或锭子油和/或单氯萘,优选α-单氯萘。
蒸发系数大于35和闪点大于30℃,优选大于45℃的低挥发性的有机油或油状溶剂可部分地被高或中挥发度的有机化学溶剂代替,条件是溶剂混合物的蒸发系数大于35和闪点大于30℃,优选大于45℃,且在溶剂混合物中杀虫剂/杀真菌剂混合物是可溶或可乳化的。
根据优选的实施方案,优选使用的一些有机化学溶剂或溶剂混合物可用脂族极性有机化学溶剂或溶剂混合物代替。脂族有机化学溶剂优选包括羟基和/或酯和/或醚基团,例如,乙二醇醚、酯等。
在本发明中使用的有机化学粘合剂是现有技术中已知的合成树脂和/或粘合剂干性油,它们是水可稀释和/或在使用的有机化学溶剂中可溶或分散或乳化的,具体的粘合剂包括或包含丙烯酸树脂、乙烯基树脂,例如乙酸聚乙烯酯、聚酯树脂、缩聚或多加成树脂、聚尿烷树脂、烷基树脂或改性烷基树脂、酚树脂、烃树脂,如茚并-香豆树脂、硅氧烷树脂、干性植物油和/或干性油和/或以天然和/或合成树脂为基础的物理干性粘合剂。
在乳剂、分散剂或液剂的剂型中可使用合成树脂粘合剂。沥青或沥青类物质也可用作粘合剂,其用量最多10重量%。还可使用现有技术中已知的染料、颜料、防水剂、除臭剂和防味剂或防锈剂等。
根据本发明的组合物或浓缩物优选包含作为有机化学粘合剂的至少一种烷基树脂或改性烷基树脂和/或一种干性植物油。根据本发明优选使用的烷基树脂的油含量大于45%重量,优选50至68%重量。
上述所有的或一些粘合剂可被固定剂(混合物)或增塑剂(混合物)替代。上述添加剂是为了防止活性成分蒸发、结晶或沉淀。它们优选代替0.01至30%的粘合剂(使用的粘合剂为100%)。
增塑剂来源于化学种类邻苯二甲酸酯,如邻苯二甲酸二丁基酯、二辛基酯或苄基丁基酯,磷酸酯,如磷酸三丁基酯,己二酸酯,如己二酸二-(2-乙基己基)酯,硬脂酸酯,如硬脂酸丁基酯或硬脂酸戊基酯,油酸酯,如油酸丁基酯,甘油醚或较高分子量乙二醇醚,甘油酯和对甲苯磺酸酯。
固定剂以聚乙烯烷基醚为基础,例如聚乙烯甲基醚或酮,如二苯酮或亚乙基二苯酮。
可用的溶剂或稀释剂最好为水,如果需要可为水与一或多种上述有机化学溶剂或稀释剂、乳化剂和分散剂的混合物。
特别有效的木材防腐方法是通过大工业规模的浸渍方法完成的,例如真空、双真空或压力方法。
如果需要,现用组合物还可包含其它杀虫剂,如果需要,还可包含一或多种杀真菌剂。
优选的混用杀虫剂和杀真菌剂描述在WO94/29268中。在上述文件中述及的化合物是本申请中明确说明的成分。
更特别优选的混用药剂可以是杀虫剂,如毒死蜱、辛硫磷、氟硅菊酯、顺式氯氰菊酯、氟氯氰菊酯、氯氰菊酯、溴氰菊酯、氯菊酯、吡虫啉、啶虫脒、氟虫脲、氟铃脲、四氟菊酯、thiacloprid,甲氧基苯氧化物和杀铃脲,以及杀真菌剂,如氧唑菌、己唑醇、戊环唑、丙环唑、戊唑醇、环丙唑醇、叶菌唑、抑霉唑、抑菌灵、甲苯氟磺胺、3-碘-2-丙炔基-丁基氨基甲酸酯、N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
同时还可使用本发明化合物保护与盐水或咸水接触的物品防污,上述物品如船体、隔板、网、建筑物、停泊处和信号系统。
寡毛菊属固着的污物可增加船牵引的摩擦,结果由于较高能量消耗和在干燥码头的频繁停留使得运行的费用明显增加,寡毛菊属例如龙介虫科,鹅茎藤壶属(鹅颈藤壶)的外壳和品种,如多种茗荷属和铠茗荷属的品种,或藤壶亚目类(藤壶)的品种,如藤壶属或Pollicipes品种。
除去藻类,如水云属和仙菜属的污染,软甲亚纲,如蔓足亚纲(甲壳纲蔓脚类动物)的固着污染也特别重要。
令人惊奇的是,现已发现本发明化合物单独或与其它活性化合物的组合物具有明显的防污活性。
使用单独的或与其它活性化合物组合的根据本发明化合物,可省却使用重金属化合物或使其浓度大大降低,重金属化合物例如存在于,二(三烷基锡)硫化物、三正丁基锡月桂酸盐、氯化三正丁基锡、氧化铜(I)、氯化三乙基锡、三正丁基(2-苯基-4-氯苯氧基)锡、氧化三丁基锡、二硫化钼、氧化锑、酞酸丁酯聚合物,氯化苯基(二吡啶)-铋、氟化三正丁基锡、亚乙基二硫氨基甲酸锰、二甲基二硫氨基甲酸锌、亚乙基二硫氨基甲酸锌、2-吡啶硫醇1-氧化物锌盐和铜盐、双二甲基二硫氨基甲酰基锌亚乙基二硫代氨基甲酸酯、氧化锌、亚乙基-双二硫氨基酸铜(I)、硫氰酸铜、萘酸铜和卤化三丁基锡。
如果需要,现用的防污油漆中还可包含其它活性化合物,优选杀藻剂、杀真菌剂、除草剂、杀螺剂,或其它防污活性化合物。
与本发明防污组合物组合的优选成分为
杀藻剂如
2-叔丁基氨基-4-环丙基氨基-6-甲硫基-1,3,5-三嗪,双氯酚、敌草隆、菌多酸、乙酸锡、异丙隆、甲基苯噻隆、乙氧氟草醚、灭藻醌和特丁津;
杀真菌剂如苯并[b]噻吩羧酸环己基酰胺S,S-二氧化物、抑菌灵、灭菌丹、3-碘-2-丙炔基丁基氨基甲酸酯、甲苯氟磺胺和唑类如戊环唑、环丙唑醇、氧唑菌、己唑醇、叶菌唑、丙环唑和戊唑醇;
杀螺剂如乙酸锡、四聚甲醛、甲硫威、杀螺胺、硫双威和混杀威;
或常规的防污活性化合物如4,5-二氯-2-辛基-4-异噻唑啉-3-酮、二碘甲基paratryl砜、2-(N,N-二甲基硫代氨基甲酰基硫)-5-硝基噻唑基、2-吡啶硫醇1-氧化物钾、铜、钠和锌盐,吡啶-三苯基硼烷、四丁基二锡氧烷、2,3,5,6-四氯-4-(甲基磺酰基)-吡啶、2,4,5,6-四氯异邻苯二甲腈、四甲基秋兰姆二硫化物和2,4,6-三氯苯基马来酰亚胺。
使用的防污组合物中包含的本发明化合物的本发明活性物质的浓度为0.001至50%重量,特别是0.01至20%重量。
而且,本发明防污组合物中包含一些常规的成分,例如在Ungerer,Chem.Ind.1985,37,730-732和Williams,AntifoulingMarine Coatings,Noyes,Park Ridge,1973中所述。
除了杀藻剂、杀真菌剂、杀螺剂活性化合物和根据本发明的杀虫剂活性化合物,防污漆中还特别包含粘合剂。
已知的粘合剂的实例为在溶剂系统中的氯化聚乙烯、在溶剂系统中的氯化橡胶、在溶剂系统中的丙烯酸树脂,特别是在水系统中,氯化乙烯/乙酸乙烯酯共聚物系统的水分散液剂型或有机溶剂系统的剂型,丁二烯/苯乙烯/丙烯腈橡胶,干性油如亚麻油,与焦油或沥青和环氧化物组合的树脂酯或改性硬化树脂,少量的氯化橡胶、氯化聚丙烯和乙烯树脂。
如果需要,油漆中还包含优选不溶于盐水中的无机颜料、有机颜料或着色剂。油漆还包含如松香的物质以控制释放活性化合物。而且,油漆还包含增塑剂、影响流变性质的改性剂和其它常规的成分。本化合物或上述混合物中还可加入自身擦光防污系统。
本活性化合物还适合防治在密闭空间中的有害动物,特别是昆虫、蜱和螨,密闭空间例如房屋、车间、办公室、车舱等。它们还可用作室内杀虫剂产品,单独或与其它活性化合物和助剂组合防治上述有害动物。它们对敏感和抗性的品系,以及对各种发育阶段的有害动物都有活性。上述有害动物包括:
蝎目,例如钳蝎(Buthus occitanus);
蜱螨目,例如波斯锐缘蜱、翘缘锐缘蜱、苔螨属、鸡皮刺螨、家食甜螨、非洲钝缘蜱、血红扇头蜱、恙螨属(Trombiculaalfreddugesi)、Neutrombicula autumnalis、屋生螨和粉尘螨。
园蛛目,例如麦羽螨科和园蛛科。
盲蛛目,例如伪蝎目(Peudoscorpiones chelifer)、Pseudoscorpiones cheiridium和Opiliones phalangium。
等足目,例如潮虫和鼠妇。
倍足纲,例如Blaniulus guttulatus和山蛩虫属。
唇足目,例如地蜈蚣属。
缨尾目,例如毛衣鱼属、西洋衣鱼和Lepismodes inquilinus。
蜚蠊目,例如东方蜚蠊、德国小蠊、小蠊(Blattella asahinai)、马得拉蜚蠊、角腹蠊属、木蠊属、澳州大蠊、美洲大蠊、褐斑大蠊、黑胸大蠊和长须蜚蠊。
跳跃亚目,例如家蟋。
革翅目,例如欧洲球螋。
等翅目,例如木白蚁属、Reticulitermes属。
啮齿目,例如书虱属和粉啮虫属。
鞘翅目,例如圆皮蠹属、毛皮蠹属、皮蠹属、长头谷盗、隐跗郭公虫属、翼窃蠹属、谷蠹、谷象、米象、玉米象和药材甲。
双翅目,例如埃及伊蚊、白纹伊蚊、伊蚊(Aedestaeniorhynchus)、按蚊属、红头丽蝇、高额麻虻、致倦库蚊、淡色库蚊、跗斑库蚊、果蝇属、夏厕蝇、家蝇、白蛉属、麻蝇(Sarcophagacarnaria)、蚋属、厩螫蝇和沼泽大蚊。
鳞翅目,例如小蜡螟、蜡螟、印度谷斑螟、木塞谷蛾、袋谷蛾和幕谷蛾。
蚤目,例如犬栉首蚤、猫栉首蚤、人蚤、穿皮潜蚤和印鼠客蚤。
膜翅目,例如广布弓背蚁、亮毛蚁、黑毛蚁、毛蚁(Lasiusumbratus)、小白蚁、Paravespula spp.和铺道蚁。
虱目,例如头虱、体虱和阴虱。
异翅亚目,例如热带臭虫、温带臭虫、长红猎蝽和侵扰锥猎蝽。
本发明化合物可单独用作室内杀虫剂,或与其它适合的活性成分如磷酸酯、氨基甲酸酯、除虫菊酯、生长调节剂或其它类已知杀虫剂活性化合物组合用作室内杀虫剂。
它们可用于气雾剂、不加压的喷雾制品,例如泵和弥雾喷雾、自动雾化系统、雾化剂、泡沫、胶、蒸发剂和纤维素或塑料制备的蒸发片剂、液体蒸发剂、胶和膜蒸发剂、驱动蒸发剂、不耗能或被动的蒸发系统、驱虫纸、驱虫袋和驱虫胶、在散布饵料中或放置饵料处的颗粒剂或粉剂。
根据本发明活性化合物的制备和应用可参见下述实施例。
制备实施例
方法(A)
在5℃下先加入三氟乙酸(185.37g,1.63mol)。在此温度下,滴加4-[1-[(叔丁氧羰基)氨基]-4-(2,6-二氟苯基)-4-氧代丁基]苯基三氟甲烷磺酸酯(II-1)(42.55g,纯度80.8%
0.06mol)的二氯甲烷(150ml)溶液,然后在此温度下搅拌混合物3小时。在减压条件下蒸出三氟乙酸,剩余物用1N NaOH调节至pH12。用二氯甲烷(2×100ml)提取水相。合并的有机相用硫酸钠充分干燥、过滤并浓缩。粗产物用硅胶色谱纯化(流动相:正己烷/乙酸乙酯3∶1(v/v))。
得到15.83g(理论值的65%)的4-[5-(2,6-二氟苯基)-3,4-二氢-2H-吡咯-2-基]苯基三氟甲磺酸酯(I-1)。
HPLC:Log P(pH2.3)=3.49(100%纯度).
1H-NMR:δ(CD3CN)=1.80(1H,m),2.65(1H,m),3.07(2H,m),5.34(1H,m),
7.08(2H,m),7.37(2H,d),7.50(3H,m)ppm.
实施例2
类似于实施例1获得(2R)-4-[5-(2,6-二氟苯基)-3,4-二氢-2H-吡咯-2-基]苯基三氟甲磺酸酯(I-2)。
HPLC:logP(pH2.3)=3.55。
旋光度:[α]D=+34.1(c=0.92,氯仿),20℃。
实施例3
类似于实施例1获得4’-[5-(2,6-二氟苯基)-3,4-二氢-2H-吡咯-2-基]-1,1’-联苯-4-基1,1,2,2,3,3,4,4,4-九氟-1-丁烷磺酸酯(I-3)。HPLC: Log P(pH2.3)=5.57(100%纯度)。m.p. 68-69℃1H-NMR:δ(CD3CN)=1.85(1H,m),2.67(1H,m),3.06(2H,m),5.34(1H,m),
7.09(2H,m),7.46(5H,d),7.65(2H,d),7.77(2H,d)ppm。
实施例4
类似于实施例1获得4’-[5-(2,6-二氟苯基)-3,4-二氢-2H-吡咯-2-基]-1,1’-联苯-4-基-二甲基氨基磺酸酯(I-3)。用硅胶色谱纯化粗产物(流动相:环己烷/乙酸乙酯1∶1),然后用异丙醇研制。HPLC: Log P(pH2.3)=3.06(100%纯度)。m.p. 131-133℃1H-NMR:δ(CD3CN)=1.83(1H,m),2.62(1H,m),3.06(2H,m),5.33(1H,m),
7.07(2H,m),7.38(2H,d),7.42(2H,d),7.45(1H,m),7.65(2H,d),
7.71(2H,d)ppm。
方法(A)原料的制备
式(II)的氨基酮类化合物
实施例(II-1)
先将1,3-二氟苯(11.04g,96.7mmol)加入四氢呋喃(100ml)中并冷却到-70℃。在此温度下,滴加正丁基锂(61.3ml,96.7mmol)。将反应混合物加热至-30℃,并在此温度下滴加2-氧代-5-(4-{[(三氟甲基)磺酰基]氧基}苯基)-1-吡咯烷甲酸叔丁基酯(VI-1)(36.0g,87.9mmol)的四氢呋喃(100ml)溶液。在-30℃下搅拌反应混合物4小时,然后在室温下搅拌16小时。将反应混合物在水(1000ml)中搅拌并用乙酸乙酯(2×500ml)提取。用1N HCl、饱和碳酸氢钠水溶液和饱和氯化钠水溶液连续冲洗合并的有机相。有机相用硫酸钠充分干燥、过滤并浓缩。
得到42.55g(理论值的75%)的4-[1-[(叔丁氧基羰基)氨基]-4-(2,6-二氟苯基)-4-氧代丁基]苯基三氟基甲烷磺酸酯(II-1)
HPLC:logP(pH2.3)=4.38(纯度81%)。
实施例(II-2)
类似于实施例(II-1)获得4-[(1R)-1-[(叔丁氧基羰基)氨基]-4-(2,6-二氟苯基)-4-氧代丁基]苯基三氟基甲烷磺酸酯(II-2)
HPLC:logP(pH2.3)=4.37。
实施例(II-3)
类似于实施例(II-1)获得4’-[1-[(叔丁氧基羰基)氨基]-4-(2,6-二氟苯基)-4-氧代丁基]-1,1’-联苯-4-基-1,1,2,2,3,3,4,4,4-九氟-1-丁烷磺酸酯(II-3)。粗产物用硅胶色谱纯化(流动相:正己烷/乙酸乙酯9∶1)
HPLC:logP(pH2.3)=6.05(纯度97.60%)。
m.p.90-92℃
类似于实施例(II-1)获得4-(2,6-二氟苯基)-1-(4’-{[(二甲基氨基)磺酰基]氧基}-1,1’-联苯-4-基)-4-氧代丁基氨基甲酸叔丁酯(II-4)。
HPLC:logP(pH2.3)=4.25。
式(VII)的N-Boc-内酰胺
在0℃,氩气氛下,先将4-(5-氧代-2-吡咯烷基)苯基三氟甲磺酸酯(154.63g,0.50mol)加入二氯甲烷中(600ml)。在此温度下,连续加入联二碳酸二叔丁基酯(218.25g,1.0mol)和二甲基氨基吡啶(6.10g,0.05mol)。然后在室温下搅拌混合物48小时。用1N HCl(2×500ml)、饱和碳酸氢钠水溶液和饱和氯化钠水溶液连续冲洗反应混合物。有机相用硫酸钠充分干燥、过滤并浓缩。
得到198.70g(理论值的99%)的2-氧代-5-(4-{[(三氟甲基)磺酰基]氧基}苯基)-1-吡咯烷甲酸叔丁基酯(VII-1)。
HPLC:logP(pH2.3)=3.31(纯度98.80%)。
在室温下通过液相色谱分离4-(5-氧代-2-吡咯烷基)苯基三氟甲磺酸酯的外消旋体,在手性固定相聚酰胺硅胶(以N-甲基丙烯酰-L-亮氨酸-d-基酰胺单体为基质,粒径:10μm,柱面积:450mm×75mm)上使用流动相乙酸乙酯(流动速率:100ml/min)并用测光仪检测(λ=254nm)。为了进行色谱分离,在11乙酸乙酯中制备40g外消旋体的溶液。色谱分离6g(=150ml的溶液)。然后分析检测对映体的纯度,合并洗脱液的适当馏份并在减压条件下充分浓缩,过滤掉剩余物,用正庚烷冲洗后干燥。
得到4-(5-氧代-(2R)-2-吡咯烷基)苯基三氟甲磺酸酯.
旋光度:[α]D=+22.8(c=0.9,甲醇),20℃。
然后类似于实施例(VII-1)使(R)-对映体反应,得到2-氧代-(5R)-5-(4-([(三氟甲基)磺酰基]氧基}苯基)-1-吡咯烷甲酸叔丁基酯(V-II)。
HPLC:logP(pH2.3)=3.31
类似于实施例(VII-1)获得2-(4’-{[(1,1,2,2,3,3,4,4,4-九氟丁基)磺酰基]氧基}-1,1’-联苯-4-基)-5-氧代-1-吡咯烷甲酸叔丁基酯(VII-3)。用硅胶色谱纯化粗产物(流动相:正己烷/乙酸乙酯3∶1)。
HPLC:logP(pH2.3)=5.44(纯度98.6%)。
m.p.115-117℃
类似于实施例(VII-1)制备2-(4’-{[(二甲基氨基)磺酰基]氧基}-1,1’-联苯-4-基)-5-氧代-1-吡咯烷甲酸叔丁基酯(VII-4)。粗产物用异丙醇重结晶,
HPLC:logP(pH2.3)=3.31(纯度98.17%)。
m.p.171-173℃
式(IX-b)的内酰胺
在0℃先加入氟化氢(50ml)。滴加5-乙氧基-2-吡咯烷酮(2.58g,0.02mol)和1,1’-联苯-4-基二甲基氨基磺酸酯(XII-2)(2.77g,0.01mol)的二氯甲烷(15ml)溶液,然后在室温下搅拌反应混合物。在减压下除去HF,剩余物用二氯甲烷吸收并用饱和碳酸氢钠水溶液冲洗。用硫酸镁充分干燥有机相,过滤并浓缩。粗产物不需要进-步提纯就可进行反应。
得到3.20g(理论值的59%)的4’-(5-氧代-2-吡咯烷基)-1,1’-联苯-4-基-二甲基氨基磺酸酯(IX-b-1)和“邻位”异构体2’-(5-氧代-2-吡咯烷基)-1,1’-联苯-4-基-二甲基氨基磺酸酯的混合物。
HPLC(IX-b-1):logP(pH2.3)=2.23(纯度66.49%)。
HPLC(“邻位”异构体):logP(pH2.3)=2.28(纯度23.81%)。
类似于实施例(IX-b-1)获得4’-(5-氧代-2-吡咯烷基)-1,1’-联苯-4-基1,1,2,2,3,3,4,4,4-九氟-1-丁烷磺酸酯(IX-b-2)。
HPLC:logP(pH2.3)=4.21(纯度88.60%)。
式(XIII)的联苯类化合物
将4-羟基联苯(1.70g,0.01mol)和碳酸钾(1.66g,0.012mol)悬浮于乙腈(50ml)中。在室温下滴加1,1,2,2,3,3,4,4,4-九氟丁烷-1-磺酰氯(3.60g,0.01mol),然后在室温下搅拌混合物16小时。过滤掉乙腈,向剩余物中加入水。吸滤过滤掉沉淀并干燥。
得到4.45g(理论值的99%)的1,1’-联苯-4-基-1,1,2,2,3,3,4,4,4-九氟-1-丁烷磺酸酯(XIII-1)。
HPLC:logP(pH2.3)=5.81(纯度100%)。
实施例(XIII-2)
将4-羟基联苯(1.70g,0.01mol)和碳酸钾(1.66g,0.012mol)悬浮于乙腈(50ml)中,在室温下搅拌1.5小时然后冷却到0℃。滴加二甲基氨基磺酰基氯(1.44g,0.01mol),然后将反应混合物在室温下搅拌16小时。吸滤过滤掉沉淀并蒸馏乙腈。剩余物用异丙醇重结晶。
得到1.81g(理论值的65%)的1,1’-联苯-4-基-二甲基氨基磺酸酯(XIII-2),熔点105-107℃。
HPLC:logP(pH2.3)=3.51(纯度99.6%)。
方法(B)
实施例5
将4’-[(2R)-5-(2,6-二氟苯基)-3,4-二氢-2H-吡咯-2-基]-1,1’-联苯-4-醇(7.0g,0.02mol)悬浮于甲苯(150ml)中。在室温下加入氢氧化钠水溶液(1.3ml,浓度45%),然后在室温下搅拌混合物45分钟。滴加三氟甲磺酰氯(2.34ml,0.022mol),然后在室温下搅拌混合物1.5小时。从固体剩余物中滗析掉甲苯相,用1N NaOH、饱和碳酸氢钠水溶液和饱和氯化铵水溶液连续冲洗,用硫酸钠充分干燥,在减压下过滤并浓缩。用硅胶色谱(流动相:环己烷/乙酸乙酯,9∶1 v/v)和随后用制备HPLC(Kromasil 100-5 C18,250×50mm;CH3CN/H2O,80∶20 v/v)纯化粗产物。
得到2.36g(理论值的25%)的4’-[(2R)-5-(2,6-二氟苯基)-3,4-二氢-2H-吡咯-2-基]-1,1’-联苯-4-基三氟甲烷磺酸酯(I-4),熔点109℃。
HPLC:logP(pH2.3)=4.27(纯度99.88%)
旋光度:[α]D=+31.8(c=0.39,MeOH);20℃
将4-[5-(2,6-二氟苯基)-3,4-二氢-2H-吡咯-2-基]苯酚(2.00g,7.3mmol)悬浮于甲苯(30ml)中。在室温下连续加入氢氧化钠水溶液(0.7ml,浓度45%,v/v)和4-(三氟甲氧基)苯磺酰氯(1.90g,7.3mmol)。在45℃下搅拌反应混合物12小时。冷却到室温后,进行相分离。用乙酸乙酯提取水相。用水冲洗合并的有机相,用硫酸钠充分干燥,过滤并浓缩。粗产物用硅胶色谱纯化(流动相:甲苯/乙酸乙酯,9∶1 v/v)。
得到2.55g(理论值的70%)的4-[5-(2,6-二氟苯基)-3,4-二氢-2H-吡咯-2-基]苯基4-(三氟甲氧基)苯磺酸酯(I-5)。
HPLC: Log P(pH2.3)=3.83(98.6%纯度)。
1H-NMR:δ(CD3CN)=1.75(1H,m),2.60(1H,m),3.05(2H,m),5.26(1H,m),
7.01(2H,d),7.07(2H,m),7.31(2H,d),7.48(1H,m),7.50(2H,d),
7.93(2H,d)ppm。
方法(C)
在氩气氛下,将5-(2.6-二氟苯基)-2-[4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂戊环-2-基)苯基]-3,4-二氢-2H-吡咯(V-1)(0.96g,2.5mmol),4-碘苯基三氟甲磺酸酯(1.06g,3.0mmol),碳酸氢钠水溶液(5ml,2M)和PdCl2dppf(56mg,0.075mmol)在二甲氧基乙烷(30ml)中在60℃下加热1.5小时,然后在80℃下加热1.5小时。冷却后,将水和乙酸乙酯加入到反应混合物中。有机相用硫酸钠充分干燥并过滤。加入硅酸镁载体(5g)并将混合物浓缩至干。粗产物用硅胶色谱纯化(流动相:环己烷/乙酸乙酯,9∶1 v/v)。
得到0.62g(理论值的52%)的4’-[5-(2,6-二氟苯基)-3,4-二氢-2H-吡咯-2-基]-1,1’-联苯-4-基三氟甲磺酸酯(I-7)。
HPLC: Log P(pH2.3)=4.15(96%纯度)。
m.p. 73-75℃。
1H-NMR:δ(CD3CN)=1.88(1H,m),2.68(1H,m),3.06(2H,m),5.35(1H,m),
7.08(2H,d),7.47(5H,m),7.65(2H,m),7.78(2H,d)ppm。
还获得0.20g化合物(I-7)的馏份(理论值的14%),纯度87%。
在氩气氛下,将4-[5-(2,6-二氟苯基)-3,4-二氢-2H-吡咯-2-基]苯基三氟甲磺酸酯(I-1)(60.80g,0.15mmol),二频哪醇二硼化物(41.90g,0.165mmol),碳酸钾(44.20g,0.45mol),PdCl2dppf(3.30g,4.50mmol)和二苯基膦基二茂铁(2.50g,4.50mmol)在二噁烷(900ml)中在80℃下加热16小时。冷却后,将反应混合物在水(1000ml)中搅拌并用乙酸乙酯(2×600ml)提取。合并的有机相用硫酸钠充分干燥并过滤。加入硅酸镁载体(200g),并将混合物蒸发至干。粗产物用硅胶色谱纯化(流动相:环己烷/乙酸乙酯,4∶1 v/v)。
得到52.80g(理论值的89%)的5-(2,6-二氟苯基)-2-[4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂戊环-2-基)苯基]-3,4-二氢-2H-吡咯(V-1)。
HPLC: Log P(pH7.5)=4.46(96.7%纯度)。
1H-NMR:δ(CD3CN)=1.32(12H,s),1.78(1H,m),2.59(1H,m),3.03(2H,m),
5.30(1H,m),7.07(2H,d),7.35(2H,m),7.46(1H,m),7.70(2H,d)
ppm.
表中和上述制备实施例给出的logP值是根据EEC-Directive79/831 Annex V.A8,用HPLC(高效液相色谱)采用反相柱(C18)测定的。温度:43℃。
测定是在酸性范围,在pH2.3,使用流动相0.1%磷酸水溶液和乙腈进行的;线性梯度为10%乙腈至90%乙腈。
测定是在中性范围,在pH7.5,使用流动相0.01摩尔磷酸缓冲水溶液和乙腈进行的;线性梯度为10%乙腈至90%乙腈。
用已知logP值的直链烷-2-酮(3至16个碳原子)进行校正(logP值是在两个连续烷酮之间采用线性内插方法通过测定保留时间而确定的)。
λ最大值的确定采用200nm至400nm的UV谱的最大色谱信号。
药效实施例
实施例A
棉蚜试验
溶剂: 30重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了生产活性化合物的适当的制剂,将1重量份的活性化合物与设定量的溶剂和乳化剂混合,并将浓缩物用包含乳化剂的水稀释至所需浓度。
将被棉蚜(Aphis gossypii)严重侵染的棉叶(Gossypiumhirsutum)在所需浓度的活性化合物的制备物中浸渍处理。
在所需时间后,确定致死率%。100%意为所有的蚜虫已经被杀死;0%意为没有蚜虫被杀死。
在此试验中,例如下述制剂实施例的化合物显示出的好的活性:
活性化合物、活性化合物的浓度和试验结果示于下表。
表A:棉蚜试验
实施例B
烟芽夜蛾试验
溶剂: 30重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了生产活性化合物的适当的制剂,将1重量份的活性化合物与设定量的溶剂和乳化剂混合,并将浓缩物用包含乳化剂的水稀释至所需浓度。
将大豆苗(Glycine max)在所需浓度的活性化合物的制备物中浸渍处理,在叶片仍保持湿润时,接种烟芽夜蛾幼虫。
在所需时间后,确定致死率%。100%意为所有的幼虫已经被杀死;0%意为没有幼虫被杀死。
活性化合物、活性化合物的浓度和试验结果示于下表。
表B:烟芽夜蛾试验
实施例C
桃蚜试验
溶剂: 30重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了生产活性化合物的适当的制剂,将1重量份的活性化合物与设定量的溶剂和乳化剂混合,并将浓缩物用包含乳化剂的水稀释至所需浓度。
将被桃蚜(Myzus persicae)严重侵染的甘蓝叶(Brassicaoleracea)在所需浓度的活性化合物的制备物中浸渍处理。
在所需时间后,确定致死率%。100%意为所有的蚜虫已经被杀死;0%意为没有蚜虫被杀死。
活性化合物、活性化合物的浓度和试验结果示于下表。
实施例D
根节线虫试验
溶剂: 30重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了生产活性化合物的适当的制剂,将1重量份的活性化合物与设定量的溶剂和乳化剂混合,并将浓缩物用包含乳化剂的水稀释至所需浓度。
将盆用砂土、活性化合物溶液、南方根节线虫卵/幼虫(Meloidogyne incognita)悬浮液和莴苣种子填充。莴苣种子萌发,植物发育。在根部长出虫瘿。
在所需时间后,通过形成的虫瘿,确定杀线虫活性%。100%意为没有发现虫瘿;0%意为被处理植物上的虫瘿数与未处理对照相同。
活性化合物、活性化合物的浓度和试验结果示于下表。
实施例E
全爪螨试验
溶剂: 3重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了生产活性化合物的适当的制剂,将1重量份的活性化合物与设定量的溶剂和乳化剂混合,并将浓缩物用包含乳化剂的水稀释至所需浓度。
将被各种发育阶段的桔全爪螨(Panonychus ulmi)严重侵染的大约30cm高的李树(Prunus domestica)用所需浓度的活性化合物的制备物喷雾。
在所需时间后,确定致死率%。100%意为所有的螨已经被杀死;0%意为没有螨被杀死。
活性化合物、活性化合物的浓度和试验结果示于下表。
表E:全爪螨试验
实施例F
蜡根猿叶甲幼虫试验
溶剂: 30重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了生产活性化合物的适当的制剂,将1重量份的活性化合物与设定量的溶剂和乳化剂混合,并将浓缩物用包含乳化剂的水稀释至所需浓度。
将甘蓝叶(Brassica oleracea)在所需浓度的活性化合物的制备物中浸渍处理,在叶片仍保持湿润时,接种蜡根猿叶甲(Phaedoncochleariae)幼虫。
在所需时间后,确定致死率%。100%意为所有的甲虫幼虫已经被杀死;0%意为没有甲虫幼虫被杀死。
活性化合物、活性化合物的浓度和试验结果示于下表。
表F:蜡根猿叶甲试验
实施例G
菜蛾试验
溶剂:30重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了生产活性化合物的适当的制剂,将1重量份的活性化合物与设定量的溶剂和乳化剂混合,并将浓缩物用包含乳化剂的水稀释至所需浓度。
将甘蓝叶(Brassica oleracea)在所需浓度的活性化合物的制备物中浸渍处理,在叶片仍保持湿润时,接种菜蛾幼虫(Plutellaxylostella)。
在所需时间后,确定致死率%。100%意为所有的幼虫已经被杀死;0%意为没有幼虫被杀死。
活性化合物、活性化合物的浓度和试验结果示于下表。
表G:菜蛾试验
实施例H
甜菜夜蛾试验
溶剂: 30重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了生产活性化合物的适当的制剂,将1重量份的活性化合物与设定量的溶剂和乳化剂混合,并将浓缩物用包含乳化剂的水稀释至所需浓度。
将甘蓝叶(Brassica oleracea)在所需浓度的活性化合物的制备物中浸渍处理,在叶片仍保持湿润时,接种甜菜夜蛾幼虫(Spodopteraexigua)。
在所需时间后,确定致死率%。100%意为所有的幼虫已经被杀死;0%意为没有幼虫被杀死。
活性化合物、活性化合物的浓度和试验结果示于下表。
实施例I
草地粘虫试验
溶剂: 30重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了生产活性化合物的适当的制剂,将1重量份的活性化合物与设定量的溶剂和乳化剂混合,并将浓缩物用包含乳化剂的水稀释至所需浓度。
将甘蓝叶(Brassica oleracea)在所需浓度的活性化合物的制备物中浸渍处理,在叶片仍保持湿润时,接种粘虫幼虫(Spodopterafrugiperda)。
在所需时间后,确定致死率%。100%意为所有的幼虫已经被杀死;0%意为没有幼虫被杀死。
活性化合物、活性化合物的浓度和试验结果示于下表。
实施例J
叶螨试验(有机磷抗性/浸沾试验)
溶剂: 30重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了生产活性化合物的适当的制剂,将1重量份的活性化合物与设定量的溶剂和乳化剂混合,并将浓缩物用包含乳化剂的水稀释至所需浓度。
将被各种发育阶段的棉叶螨(Tetranychus urticae)严重侵染的大豆植株(Phaseolus vulgaris)在所需浓度的活性化合物的制备物中浸沾。
在所需时间后,确定活性率%。100%意为所有的螨已经被杀死;0%意为没有螨被杀死。
活性化合物、活性化合物的浓度和试验结果示于下表。
表J:叶螨试验
实施例K
黄瓜条叶甲试验(在土壤中的幼虫)
临界浓度试验/土壤昆虫-转基因植物处理
溶剂: 7重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了生产活性化合物的适当的制剂,将1重量份的活性化合物与设定量的溶剂混合,加入设定量的乳化剂,并将浓缩物用水稀释至所需浓度。
将活性化合物的制剂先与土壤混合。在制剂中活性化合物的浓度实际上不很重要,只有每单位体积土壤中的活性化合物的量是决定性的,将其用ppm(mg/l)表示。用处理过的土壤填充0.25l的盆,并将其保持在20℃。
处理后立即向每个盆中种植5棵经发芽处理的玉米,品种为YIELDGUARD(Monsanto Comp.,USA的商标)。2天后,将适当的供试昆虫放入处理过的土壤中。再过7天后,通过计数出现昆虫的玉米植株数,测定活性化合物的活性率(1植株=20%活性)。
实施例L
烟芽夜蛾试验
溶剂: 7重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了生产活性化合物的适当的制剂,将1重量份的活性化合物与设定量的溶剂和乳化剂混合,并将该浓缩物用水稀释至所需浓度。
将品种为Roundup Ready(Monsanto Comp.,USA的商标)的大豆苗(Glycine max)在所需浓度的活性化合物的制备物中浸渍处理,在叶片仍保持湿润时,接种烟芽夜蛾幼虫。
在所需时间后,确定致死率%。100%意为所有的幼虫已经被杀死;0%意为没有幼虫被杀死。
实施例M
铜绿蝇幼虫试验/发育抑制活性
Lucilia cuprina(48h/DI)
供试动物:铜绿蝇幼虫
溶剂:二甲基亚砜
将20mg的活性化合物溶于1ml的二甲基亚砜中。为了制备适当的制剂,分别将活性化合物用水稀释到所需浓度。
将大约20只铜绿蝇幼虫(Lucilia cuprina)放入包括大约1cm3的马肉和0.5ml供试活性化合物制剂的试管中。48小时后测定活性化合物制剂的活性,用幼虫死亡率%表示。
然后将试管移至底部铺有砂土的烧杯中。再过12天后,移出试管并计数蛹和蝇数。发育的抑制作用,用未处理对照1.5倍发育期后抑制孵化的%(已孵化成蝇的蛹的比例)表示。
活性化合物,活性化合物浓度和试验结果如下表所示。
表M:铜绿蝇试验
实施例N
杂食性蜱若虫试验,浸沾处理
花蜱(Amblyomma hebraeum)(DI)
供试动物:己经吸食满的花蜱幼虫
溶剂:二甲基亚砜
将20mg的活性化合物溶于1ml的二甲基亚砜中。为了制备适当的制剂,分别将活性化合物用水稀释到所需浓度。
将大约10只已经吸食满的幼虫在供试活性化合物制剂中浸没1分钟。将供试动物移至培替氏培养皿(直径9.5cm)中,培养皿中用合适的滤纸片铺垫。在气候室内储藏4周后,确定死亡率。
100%意为没有动物进行正常的蜕皮。0%意为所有的动物都进行了蜕皮。
在此试验中,例如,制备实施例的化合物(I-1)、(I-2)、(I-5)和(I-7)表现出好的活性。
Claims (19)
1.式(I)的Δ1-吡咯啉类化合物,
其中
n为0或1,
r和s各自独立地为0,1或2,
R1为卤素或甲基,
R2为氢或卤素,
R3和R4各自独立地为卤素、烷基、卤代烷基、烷氧基或卤代烷氧基,
R5为烷基、卤代烷基、各自任选被W1所列的相同或不同的基团单-或多取代的苯基或代表-NR6R7,
W1为卤素、烷基、卤代烷基、烷氧基、卤代烷氧基、烷基羰基、烷氧基羰基或-S(O)qR8,
R6为烷基或卤代烷基,
R7为氢、烷基或卤代烷基,
R6和R7还一起代表亚烷基或烷氧基亚烷基,
R8为烷基或卤代烷基和
q为0,1或2。
2.根据权利要求1的式(1)化合物,其中
n为0或1,
r和s各自独立地为0,1或2,
R1为氟、氯、溴或甲基,
R2为氢、氟、氯或溴,
R3和R4各自独立地为氟、氯、溴、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基或C1-C6卤代烷氧基,
R5为C1-C6烷基、C1-C6卤代烷基、各自任选被W1所列的相同或不同的基团单-至四取代的苯基或代表-NR6R7,
W1为氟、氯、溴、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷基羰基、C1-C6烷氧基羰基或-S(O)qR8,
R6为C1-C6烷基或C1-C6卤代烷基,
R7为氢、C1-C6烷基或C1-C6卤代烷基,
R6和R7还一起代表C3-C6亚烷基或C1-C4-烷氧基-C1-C4亚烷基,
R8为C1-C6-烷基或C1-C6-卤代烷基和
q为0,1或2。
3.根据权利要求1的式(1)化合物,其中
n为0或1,
r和s各自独立地为0,1或2,
R1为氟、氯或甲基,
R2为氢、氟或氯,
R3和R4各自独立地为氟、氯、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基,
R5为C1-C4烷基、C1-C4卤代烷基、各自任选被W1所列的相同或不同的基团单-至三取代的苯基或代表-NR6R7,
W1为氟、氯、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷基羰基、C1-C4烷氧基羰基或-S(O)qR8,
R6为C1-C4烷基或C1-C4卤代烷基,
R7为氢、C1-C4烷基或C1-C4卤代烷基,
R6和R7还一起代表C4-C5亚烷基或-(CH2)2-O-(CH2)2-,
R8为C1-C4-烷基或C1-C4-卤代烷基,
q为0,1或2。
4.根据权利要求1的式(1)化合物,其中
n为0或1,
r和s各自独立地为0或1,
R1为氟或氯,
R2为氢或氟,
R3和R4各自独立地为氟、氯、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、三氟甲基、三氟乙基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、三氟甲氧基或三氟乙氧基,
R5为甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、三氟甲基、三氟乙基、壬氟丁基、各自任选被W1所列的相同或不同的基团单-至二取代的苯基或代表-NR6R7,
W1为氟、氯、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、三氟甲基、三氟乙基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、三氟甲氧基、三氟乙氧基、-COCH3、-CO2CH3、-SCF3、-SCHF2、-SOCF3、-SOCHF2、-SO2CF3或-SO2CHF2,
R6为甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、三氟甲基或三氟乙基和
R7为氢、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、三氟甲基或三氟乙基。
5.式(I-a)化合物
其中
R1、R2、R3、R4、R5、r和s为权利要求1-4中任一的定义。
6.式(I-b)化合物
其中
R1、R2、R4、R5和s为权利要求1-4中任一的定义。
7.式(I-c)的Δ1-吡咯啉类化合物
其中
R1、R2、R4、R5和s为权利要求1-4中任一的定义。
8.式(I-d)的Δ1-吡咯啉类化合物
其中,R1、R2、R3、R4、R5、r和s为权利要求1-4中任一的定义。
9.根据权利要求1的式(I)化合物的制备方法,其特征在于
A)式(II)氨基酮用路易斯酸或质子酸处理,
其中R1、R2、R3、R4、R5、n、r和s为权利要求1中的定义,
或
其中
R1、R2、R3、R4、n、r和s为权利要求1中给出的定义,
或
(C)式(I-a)的Δ1-吡咯啉化合物
其中
n代表1,和
R1、R2、R3、R4、R5、r和s为权利要求1中给出的定义,
其制备首先是通过式(IV)的吡咯啉类化合物与二硼酸酯在催化剂存在下、在酸结合剂存在下反应且,如果需要在稀释剂存在下进行反应,
其中
R1、R2、R3、和r为上述给出的定义,和
X为Br、Cl、I、-OSO2CF3或-OSO2(CF2)3CF3,
且,如果需要在先分离所得的式(V)化合物后,式(V)化合物与式(VI)的碘化物在催化剂存在下、在二硼酸酯存在下、在酸结合剂存在
其中
R1、R2、R3和r为上述给出的定义和
G代表4,4,5,5-四甲基-1,3,2-二氧杂硼杂戊环-2-基、5,5-二甲基-1,3,2-二氧杂硼杂己环-2-基、4,4,6-三甲基-1,3,2-二氧杂硼杂己环-2-基或1,3,2-苯并二氧杂硼杂戊烯-2-基,
其中
R4,R5和s为权利要求1中的定义。
11.式(IV-b)的吡咯啉类化合物
其中
R1、R2、R3和r为权利要求1-4中任一项的定义和
X2代表-OSO2CF3。
12.式(IV-b)的吡咯啉类化合物
其中
R1、R2、R3和r为权利要求1-4中任一项的定义和
X2代表-OSO2(CF2)3CF3。
14.式(IX)的内酰胺
其中
R3、R4、R5、n、r和s为权利要求1-4中任一项的定义。
15.农药,其特征在于包含至少一种根据权利要求1的式(I)化合物,以及填充剂和/或表面活性剂。
16.根据权利要求1的式(I)化合物用于防治有害动物的用途。
17.防治有害动物的方法,其特征在于使根据权利要求1的式(I)化合物作用于有害动物和/或生长地。
18.制备农药的方法,其特征在于将根据权利要求1的式(I)化合物与填充剂和/或表面活性剂混合。
19.根据权利要求1的式(I)化合物用于制备农药的用途。
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