CN101395116B - 2,4,6-三烷基苯基取代的环戊烷-1,3-二酮 - Google Patents
2,4,6-三烷基苯基取代的环戊烷-1,3-二酮 Download PDFInfo
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- CN101395116B CN101395116B CN2007800078184A CN200780007818A CN101395116B CN 101395116 B CN101395116 B CN 101395116B CN 2007800078184 A CN2007800078184 A CN 2007800078184A CN 200780007818 A CN200780007818 A CN 200780007818A CN 101395116 B CN101395116 B CN 101395116B
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- LOGSONSNCYTHPS-UHFFFAOYSA-N cyclopentane-1,3-dione Chemical compound O=C1CCC(=O)C1 LOGSONSNCYTHPS-UHFFFAOYSA-N 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 210
- 238000000034 method Methods 0.000 claims abstract description 96
- -1 ketone carboxylic ester Chemical class 0.000 claims description 187
- 239000002585 base Substances 0.000 claims description 124
- 239000000460 chlorine Substances 0.000 claims description 88
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 87
- 229910052801 chlorine Inorganic materials 0.000 claims description 87
- 239000001257 hydrogen Substances 0.000 claims description 84
- 229910052739 hydrogen Inorganic materials 0.000 claims description 84
- 229910052731 fluorine Inorganic materials 0.000 claims description 81
- 229910052736 halogen Inorganic materials 0.000 claims description 81
- 150000002367 halogens Chemical class 0.000 claims description 81
- 239000011737 fluorine Substances 0.000 claims description 80
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 74
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 68
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 63
- 239000001301 oxygen Substances 0.000 claims description 58
- 229910052760 oxygen Inorganic materials 0.000 claims description 58
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
- 150000002431 hydrogen Chemical class 0.000 claims description 55
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 52
- 239000002253 acid Substances 0.000 claims description 51
- 125000003545 alkoxy group Chemical group 0.000 claims description 51
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 49
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 48
- 229910052794 bromium Inorganic materials 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 45
- 238000002360 preparation method Methods 0.000 claims description 45
- 239000003795 chemical substances by application Substances 0.000 claims description 43
- 229910052799 carbon Inorganic materials 0.000 claims description 42
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 244000038559 crop plants Species 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 239000011230 binding agent Substances 0.000 claims description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 23
- 150000002148 esters Chemical class 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 17
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 16
- 239000013543 active substance Substances 0.000 claims description 16
- 239000003513 alkali Substances 0.000 claims description 16
- 125000004494 ethyl ester group Chemical group 0.000 claims description 16
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 13
- 241000238631 Hexapoda Species 0.000 claims description 13
- OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 claims description 13
- MCNOFYBITGAAGM-UHFFFAOYSA-N 2,2-dichloro-1-[5-(furan-2-yl)-2,2-dimethyl-1,3-oxazolidin-3-yl]ethanone Chemical compound C1N(C(=O)C(Cl)Cl)C(C)(C)OC1C1=CC=CO1 MCNOFYBITGAAGM-UHFFFAOYSA-N 0.000 claims description 12
- VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 claims description 12
- NNYRZQHKCHEXSD-UHFFFAOYSA-N Daimuron Chemical compound C1=CC(C)=CC=C1NC(=O)NC(C)(C)C1=CC=CC=C1 NNYRZQHKCHEXSD-UHFFFAOYSA-N 0.000 claims description 12
- ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical group CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 11
- HKELWJONQIFBPO-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-(trichloromethyl)-1,2,4-triazole-3-carboxylic acid Chemical compound N1=C(C(=O)O)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl HKELWJONQIFBPO-UHFFFAOYSA-N 0.000 claims description 10
- NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 claims description 10
- 150000001266 acyl halides Chemical class 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 230000006872 improvement Effects 0.000 claims description 10
- FHCUXGCMUASJQQ-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylsulfanyl]-5-propyl-1,3,4-oxadiazole Chemical compound O1C(CCC)=NN=C1SCC1=CC=CC=C1Cl FHCUXGCMUASJQQ-UHFFFAOYSA-N 0.000 claims description 9
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 9
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 6
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 6
- 125000005936 piperidyl group Chemical group 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- XHXUANMFYXWVNG-ADEWGFFLSA-N (-)-Menthyl acetate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(C)=O XHXUANMFYXWVNG-ADEWGFFLSA-N 0.000 claims description 4
- QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 claims description 4
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 241000607479 Yersinia pestis Species 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 claims description 2
- 239000001605 (5-methyl-2-propan-2-ylcyclohexyl) acetate Substances 0.000 claims description 2
- RZMGZEJEAAVXRG-UHFFFAOYSA-N 1,2-dihydrotriazole-3-carboxylic acid Chemical compound N1NN(C=C1)C(=O)O RZMGZEJEAAVXRG-UHFFFAOYSA-N 0.000 claims description 2
- NAGITCQJDYYKJJ-UHFFFAOYSA-N 2-chloro-4-(trifluoromethyl)-1,3-thiazole Chemical compound FC(F)(F)C1=CSC(Cl)=N1 NAGITCQJDYYKJJ-UHFFFAOYSA-N 0.000 claims description 2
- YAGNTYMRLLCROP-UHFFFAOYSA-N 2-ethoxy-3,3-diphenylpropanoic acid Chemical compound C(C)OC(C(=O)O)C(C1=CC=CC=C1)C1=CC=CC=C1 YAGNTYMRLLCROP-UHFFFAOYSA-N 0.000 claims description 2
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims description 2
- SIYAHZSHQIPQLY-UHFFFAOYSA-N 4-(4-chlorophenoxy)butanoic acid Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1 SIYAHZSHQIPQLY-UHFFFAOYSA-N 0.000 claims description 2
- RDLQLVAVVVLVEW-UHFFFAOYSA-N 4-chloro-2-phenylpyrimidine Chemical compound ClC1=CC=NC(C=2C=CC=CC=2)=N1 RDLQLVAVVVLVEW-UHFFFAOYSA-N 0.000 claims description 2
- SPWZWLCUCALHPC-UHFFFAOYSA-N 5-(4-fluorophenyl)-5-phenyl-4h-1,2-oxazole-3-carboxylic acid Chemical compound C1C(C(=O)O)=NOC1(C=1C=CC(F)=CC=1)C1=CC=CC=C1 SPWZWLCUCALHPC-UHFFFAOYSA-N 0.000 claims description 2
- NOBPWDYRGXWVRL-UHFFFAOYSA-N 5-[(2,4-dichlorophenyl)methyl]-4,5-dihydro-1,2-oxazole-3-carboxylic acid Chemical compound C1C(C(=O)O)=NOC1CC1=CC=C(Cl)C=C1Cl NOBPWDYRGXWVRL-UHFFFAOYSA-N 0.000 claims description 2
- VRODIKIAQUNGJI-UHFFFAOYSA-N 5-phenyl-4,5-dihydro-1,2-oxazole-3-carboxylic acid Chemical compound C1C(C(=O)O)=NOC1C1=CC=CC=C1 VRODIKIAQUNGJI-UHFFFAOYSA-N 0.000 claims description 2
- KIKRPOGFIMUDOJ-UHFFFAOYSA-N C(C)OC(C(OCC)C(C1=CC=CC=C1)C1=CC=CC=C1)=O Chemical compound C(C)OC(C(OCC)C(C1=CC=CC=C1)C1=CC=CC=C1)=O KIKRPOGFIMUDOJ-UHFFFAOYSA-N 0.000 claims description 2
- QOFJYAIAWNGTOH-UHFFFAOYSA-N C(C)OCC(=O)O.ClC1=CC=CC(=C1)Cl Chemical compound C(C)OCC(=O)O.ClC1=CC=CC(=C1)Cl QOFJYAIAWNGTOH-UHFFFAOYSA-N 0.000 claims description 2
- FLIQZZAJPCIEKH-UHFFFAOYSA-N COC1=CC(=C(C=C1)C(=O)O)OCl Chemical compound COC1=CC(=C(C=C1)C(=O)O)OCl FLIQZZAJPCIEKH-UHFFFAOYSA-N 0.000 claims description 2
- XHXUANMFYXWVNG-UHFFFAOYSA-N D-menthyl acetate Natural products CC(C)C1CCC(C)CC1OC(C)=O XHXUANMFYXWVNG-UHFFFAOYSA-N 0.000 claims description 2
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- BWPYBAJTDILQPY-UHFFFAOYSA-N Methoxyphenone Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1=CC=CC(C)=C1 BWPYBAJTDILQPY-UHFFFAOYSA-N 0.000 claims description 2
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- OEJNXTAZZBRGDN-UHFFFAOYSA-N toxaphene Chemical compound ClC1C(Cl)C2(Cl)C(CCl)(CCl)C(=C)C1(Cl)C2(Cl)Cl OEJNXTAZZBRGDN-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- 229940116861 trichinella britovi Drugs 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
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000012873 virucide Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- 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
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- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/707—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups a keto group being part of a three- to five-membered ring
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- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
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- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
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- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
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- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
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- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
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- C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
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- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
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Abstract
本发明涉及新的式(I)的2,4,6-三烷基苯基取代的环戊烷-1,3-二酮,其中X、Y、A、B、Q1、Q2和G按权利要求中所述进行定义,涉及多种制备其的方法和中间体产物及其作为杀虫剂和/或除草剂的用途,还涉及含有式(I)的2,4,6-三烷基苯基取代的环戊烷-1,3-二酮和至少一种改进其与栽培植物相容性的组分的选择性除草剂。
Description
本发明涉及新的2,4,6-三烷基苯基取代的环戊烷-1,3-二酮、其多种制备方法及其作为杀虫剂和/或除草剂的用途。
此外,本发明涉及新的选择性除草活性化合物结合物(combination),其首先含有2,4,6-三烷基苯基取代的环戊烷-1,3-二酮衍生物,其次含有至少一种改进作物植物相容性的化合物,该结合物对于选择性防治多种有用植物作物中的杂草具有非常好的效果。
已知某些被取代的2-芳基环戊烷二酮具有除草、杀虫和杀螨特性(参见,例如US-4 283 348;4 338 122;4 436 666;4 526 723;4 551 547;4 632 698;WO96/01798;WO96/03366,WO97/14 667以及WO98/39281,WO99/43649,WO99/48869,WO99/55673,WO01/17972,WO01/74770,WO03/062244,WO04/080962,DE-A-10326386)。还已知以类似方式被取代的以下化合物:文献Micklefield et.al,Tetrahedron,(1992),7519-26公开的3-羟基-5,5-二甲基-2-苯基环戊-2-烯-1-酮和文献Edwards et al.,J.Chem.Soc.S,(1967),405-9公开的天然产物Involution(-)-顺-5-(3,4-二羟基苯基)-3,4-二羟基-2-(4-羟基苯基)-环戊-2-烯酮。但未记载杀虫或杀螨作用。此外,2-(2,4,6-三甲基苯基)-1,3-茚满二酮已知于文献J.Economic Entomology,66(1973),584和公开文本DE-A2 361 084,其除草和杀螨作用也有叙述。
但是,特别是在低的施用率和浓度时,这些化合物的活性及其活性谱并不总是完全令人满意。此外,这些化合物与某些作物植物的相容性也并不总是足够。
本发明现提供新的式(I)化合物
式中
X代表甲基,并且
Y代表甲基或乙基,或者
X和Y代表乙基,
这时
A代表氢,各自任选被卤素取代的烷基、烯基、烷氧基烷基、烷硫基烷基,饱和或不饱和的任选被取代的环烷基,其中任选至少一个环原子被杂原子替代,
B代表氢、烷基或烷氧基烷基,或者
A和B与它们所连接的碳原子一起代表一个饱和的或不饱和的、未被取代的或被取代的并且任选含有至少一个杂原子的环,
A和Q1一起代表任选被取代并可任选被一个杂原子间隔的烷二基或烯二基,
Q1和Q2相互独立地代表氢或烷基,
或者,式中
X代表乙基,
并且
Y代表甲基,
这时
A和B与它们所连接的碳原子一起代表一个饱和的或不饱和的、未被取代的或被取代的4元至8元环,
并且
Q1和Q2代表氢,
或者
A和Q1一起代表各自任选被取代并可任选被杂原子间隔的C2-C6烷二基或C2-C6烯二基,
并且
B和Q2相互独立地代表氢或烷基,
G代表氢(a)或代表以下基团之一
E代表一种金属离子或一种铵离子,
L代表氧或硫,
M代表氧或硫,
R1代表各自任选被卤素取代的烷基、烯基、烷氧基烷基、烷硫基烷基、多烷氧基烷基,或任选被卤素、烷基或烷氧基取代并可被至少一个杂原子间隔的环烷基,各自任选被取代的苯基、苯基烷基、杂芳基、苯氧基烷基或杂芳氧基烷基,
R2代表各自任选被卤素取代的烷基、烯基、烷氧基烷基、多烷氧基烷基,或代表各自任选被取代的环烷基、苯基或苄基,
R3、R4和R5相互独立地代表各自任选被卤素取代的烷基、烷氧基、烷基氨基、二烷基氨基、烷硫基、烯硫基、环烷硫基,或代表各自任选被取代的苯基、苄基、苯氧基或苯硫基,
R6和R7相互独立地代表氢,各自任选被卤素取代的烷基、环烷基、烯基、烷氧基、烷氧基烷基,代表任选被取代的苯基,代表任选被取代的苄基,或与它们所连接的氮原子一起代表一个任选被氧或硫间隔的环。
尤其是根据取代基的性质,式(I)化合物可以几何异构体或光学异构体或不同组成的异构体混合物的形式存在,所述异构体混合物,如果合适,可以常规手段进行分离。本发明提供纯异构体与异构体混合物、其制备方法和用途以及含有它们的组合物。但是,为简单起见,下文仅称式(I)的化合物,虽然其含义不仅指纯化合物,而且如果合适还指具有不同比例的异构体化合物的混合物。
根据取代基G的位置,式(I)化合物可以式(I-A)和(I-B)两种异构体的形式存在,
此即式(I)中虚线所表示的含义。
式(I-A)和(I-B)的化合物可以混合物和其纯异构体的形式存在。如果合适,式(I-A)和(I-B)化合物的混合物可通过物理方法进行分离,例如通过色谱法分离。
为清楚起见,下文中每种情形仅示出一种可能的异构体。但这并不排除在合适的情况下化合物可以异构体混合物形式或以各自的其它异构体形式而存在。
代入基团G的不同含义(a)、(b)、(c)、(d)、(e)、(f)和(g)时,产生以下基本结构(I-a)至(I-g):
其中
A、B、Q1、Q2、E、L、M、X、Y、R1、R2、R3、R4、R5、R6和R7具有以上给出的含义。
此外,已发现新的式(I)化合物可通过以下所述方法获得:
(A)式(I-a)的化合物通过式(II)的酮羧酯的分子内环化得到,该反应如果合适在一种稀释剂的存在下和一种碱的存在下进行:
式中
A、B、Q1、Q2、X和Y具有以上给出的含义,
式中
A、B、Q1、Q2、X和Y具有以上给出的含义,并且
R8代表烷基(特别是C1-C8烷基)。
而且,已发现
(B)以上所示式(I-b)的化合物——其中A、B、Q1、Q2、R1、X和Y具有以上给出的含义,通过以上所示式(I-a)的化合物——其中A、B、Q1、Q2、X和Y具有以上给出的含义——各自与以下物质反应得到:
(α)与式(III)的酰基卤反应
其中
R1具有以上给出的含义,并且
Ha1代表卤素(特别是氯或溴)
或者
(β)与式(IV)的羧酸酐反应
R1-CO-O-CO-R1 (IV)
其中
R1具有以上给出的含义,
该反应如果合适在一种稀释剂的存在下并且如果合适在一种酸结合剂的存在下进行;
(C)以上所示式(I-c)的化合物——其中A、B、Q1、Q2、R2、M、X和Y具有以上给出的含义并且L代表氧,通过以上所示式(I-a)的化合物——其中A、B、Q1、Q2、X和Y具有以上给出的含义——各自与式(V)的氯甲酸酯或氯甲酸硫代酯反应得到,该反应如果合适在一种稀释剂的存在下并且如果合适在一种酸结合剂的存在下进行:
R2-M-CO-Cl (V)
其中
R2和M具有以上给出的含义;
(D)以上所示式(I-c)的化合物——其中A、B、Q1、Q2、R2、M、X和Y具有以上给出的含义并且L代表硫,通过以上所示式(I-a)的化合物——其中A、B、D、Q1、Q2、X和Y具有以上给出的含义——各自与式(VI)的氯单硫代甲酸酯(chloromonothioformic ester)或氯二硫代甲酸酯(chlorodithioformic ester)反应得到,该反应如果合适在一种稀释剂的存在下并且如果合适在一种酸结合剂的存在下进行:
其中
M和R2具有以上给出的含义
以及
(E)以上所示式(I-d)的化合物——其中A、B、Q1、Q2、R3、X和Y具有以上给出的含义,通过以上所示式(I-a)的化合物——其中A、B、D、Q1、Q2、X和Y具有以上给出的含义——各自与式(VII)的磺酰氯反应得到,该反应如果合适在一种稀释剂的存在下并且如果合适在一种酸结合剂的存在下进行:
R3-SO2-Cl (VII)
其中
R3具有以上给出的含义,
(F)以上所示式(I-e)的化合物——其中A、B、L、Q1、Q2、R4、R5、X和Y具有以上给出的含义,通过以上所示式(I-a)的化合物——其中A、B、Q1、Q2、X和Y具有以上给出的含义——各自与式(VIII)的磷化合物反应得到,该反应如果合适在一种稀释剂的存在下并且如果合适在一种酸结合剂的存在下进行:
其中
L、R4和R5具有以上给出的含义,并且
Ha1代表卤素(特别是氯或溴),
(G)以上所示式(I-f)的化合物——其中A、B、E、Q1、Q2、X和Y具有以上给出的含义,通过式(I-a)的化合物——其中A、B、Q1、Q2、X和Y具有以上给出的含义——各自分别与式(IX)和(X)的金属化合物或胺反应得到,该反应如果合适在一种稀释剂的存在下进行:
其中
Me代表一价或二价金属(优选碱金属或碱土金属,例如锂、钠、钾、镁或钙),
t代表数值1或2,并且
R10、R11、R12相互独立地代表氢或烷基(优选C1-C8烷基),
(H)以上所示式(I-g)的化合物——其中A、B、L、Q1、Q2、R6、R7、X和Y具有以上给出的含义,通过以上所示式(I-a)的化合物——其中A、B、Q1、Q2、X和Y具有以上给出的含义——各自与以下物质反应得到:
(α)与式(XI)的异氰酸酯或异硫氰酸酯反应
R6-N=C=L (XI)
其中
R6和L具有以上给出的含义,
该反应如果合适在一种稀释剂的存在下并且如果合适在一种催化剂的存在下进行,或者
(β)与式(XII)的氨基甲酰氯或硫代氨基甲酰氯反应
其中
L、R6和R7具有以上给出的含义,
该反应如果合适在一种稀释剂的存在下并且如果合适在一种酸结合剂的存在下进行。
此外,已发现新的式(I)化合物作为杀虫剂非常有效,优选作为杀昆虫剂、杀螨剂和除草剂。
令人惊讶的是,现已发现某些被取代的环酮烯醇与以下所述改进作物植物相容性的化合物(安全剂/解毒剂)一起使用时,能有效地防止对作物植物的破坏并且可以特别有利的方式用作广谱结合物制剂用于选择性防治有用植物作物中,例如谷类以及玉米、大豆和稻中的不想要的植物。
本发明还提供含有有效量的活性化合物结合物的选择性除草组合物,含有以下组分:
(a')至少一种式(I)的化合物,式中A、B、G、Q1、Q2、X和Y具有以上给出的含义
和
(b')选自以下化合物的至少一种改进作物植物相容性的化合物:
4-二氯乙酰基-1-氧杂-4-氮杂螺[4.5]癸烷(AD-67,MON-4660)、1-二氯乙酰基-六氢-3,3,8a-三甲基吡咯并[1,2-a]-嘧啶-6(2H)-酮(dicyclonon,BAS-145138)、4-二氯乙酰基-3,4-二氢-3-甲基-2H-1,4-苯并噁嗪(解草嗪(benoxacor))、5-氯喹啉-8-氧乙酸1-甲基己基酯(解草酯(cloquintocet-mexyl)—另外参见EP-A-86750,EP-A-94349,EP-A-191736,EP-A-492366中的相关化合物)、3-(2-氯苄基)-1-(1-甲基-1-苯基乙基)脲(苄草隆(cumyluron))、α-(氰基甲氧基亚氨基)-苯基乙腈(解草胺腈(cyometrinil))、2,4-二氯苯氧基乙酸(2,4-D)、4-(2,4-二氯苯氧基)丁酸(2,4-DB)、1-(1-甲基-1-苯基乙基)-3-(4-甲基苯基)脲(杀草隆(daimuron,dymron))、3,6-二氯-2-甲氧基苯甲酸(麦草畏(dicamba))、S-1-甲基-1-苯基乙基哌啶-1-硫代羧酸酯(哌草丹(dimepiperate))、2,2-二氯-N-(2-氧代-2-(2-丙烯基氨基)乙基)-N-(2-丙烯基)乙酰胺(DKA-24)、2,2-二氯-N,N-二-2-丙烯基乙酰胺(烯丙酰草胺(dichlormid))、4,6-二氯-2-苯基嘧啶(解草啶(fenclorim))、1-(2,4-二氯苯基)-5-三氯甲基-1H-1,2,4-三唑-3-羧酸乙酯(解草唑(fenchlorazole-ethyl)—另外参见EP-A-174562和EP-A-346620中的相关化合物)、2-氯-4-三氟甲基噻唑-5-羧酸苯甲酯(解草胺(flurazole))、4-氯-N-(1,3-二氧戊环-2-基甲氧基)-α-三氟苯乙酮肟(氟草肟(fluxofenim))、3-二氯乙酰基-5-(2-呋喃基)-2,2-二甲基噁唑烷(解草恶唑(furilazole),MON-13900)、4,5-二氢-5,5-二苯基-3-异噁唑羧酸乙酯(双苯噁唑酸(isoxadifen-ethyl)—另外参见WO-A-95/07897中的相关化合物)、1-(乙氧基羰基)乙基3,6-二氯-2-甲氧基苯甲酸酯(lactidichlor)、(4-氯-o-甲苯氧基)乙酸(MCPA)、2-(4-氯-o-甲苯氧基)丙酸(2甲4氯丙酸(mecoprop))、1-(2,4-二氯苯基)-4,5-二氢-5-甲基-1H-吡唑-3,5-二羧酸二乙酯(吡唑解草酯(mefenpyr-diethyl)—另外参见WO-A-91/07874中的相关化合物)、2-二氯甲基-2-甲基-1,3-二氧戊环(MG-191)、2-丙烯基-1-氧杂-4-氮杂螺[4.5]癸-4-酸二硫代酯(MG-838)、1,8-萘二甲酸酐、α-(1,3-二氧戊环-2-基甲氧亚氨基)-苯基乙腈(解草腈(oxabetrinil))、2,2-二氯-N-(1,3-二氧戊环-2-基甲基)-N-(2-丙烯基)乙酰胺(PPG-1292)、3-二氯乙酰基-2,2-二甲基噁唑烷(R-28725)、3-二氯乙酰基-2,2,5-三甲基噁唑烷(R-29148)、4-(4-氯-o-甲苯基)丁酸、4-(4-氯苯氧基)丁酸、二苯基甲氧基乙酸、二苯基甲氧基乙酸甲酯、二苯基甲氧基乙酸乙酯、1-(2-氯苯基)-5-苯基-1H-吡唑-3-羧酸甲酯、1-(2,4-二氯苯基)-5-甲基-1H-吡唑-3-羧酸乙酯、1-(2,4-二氯苯基)-5-异丙基-1H-吡唑-3-羧酸乙酯、1-(2,4-二氯苯基)-5-(1,1-二甲基乙基)-1H-吡唑-3-羧酸乙酯、1-(2,4-二氯苯基)-5-苯基-1H-吡唑-3-羧酸乙酯(另外参见EP-A-269806和EP-A-333131中的相关化合物)、5-(2,4-二氯苄基)-2-异噁唑啉-3-羧酸乙酯、5-苯基-2-异噁唑啉-3-羧酸乙酯、5-(4-氟苯基)-5-苯基-2-异噁唑啉-3-羧酸乙酯(另外参见WO-A-91/08202中的相关化合物)、1,3-二甲基丁-1-基5-氯喹啉-8-氧乙酸酯、4-烯丙氧基丁基5-氯喹啉-8-氧乙酸酯、1-烯丙氧基丙-2-基5-氯喹啉-8-氧乙酸酯、5-氯喹喔啉-8-氧乙酸甲酯、5-氯喹啉-8-氧乙酸乙酯、5-氯喹喔啉-8-氧乙酸烯丙酯、2-氧代丙-1-基5-氯喹啉-8-氧乙酸酯、5-氯喹啉-8-氧丙二酸二乙酯、5-氯喹喔啉-8-氧丙二酸二烯丙酯、5-氯喹啉-8-氧丙二酸二乙酯(另外参见EP-A-582198中的相关化合物)、4-羧基苯并二氢吡喃-4-基乙酸(AC-304415,参见EP-A-613618)、4-氯苯氧基乙酸、3,3'-二甲基-4-甲氧基二苯甲酮、1-溴-4-氯甲基磺酰基苯、1-[4-(N-2-甲氧基苯甲酰基氨磺酰基)苯基]-3-甲基脲(也称为N-(2-甲氧基苯甲酰基)-4-[(甲氨基羰基)氨基]苯磺酰胺)、1-[4-(N-2-甲氧基苯甲酰基氨磺酰基)苯基]-3,3-二甲基脲、1-[4-(N-4,5-二甲基苯甲酰基氨磺酰基)苯基]-3-甲基脲、1-[4-(N-萘基氨磺酰基)苯基]-3,3-二甲基脲、N-(2-甲氧基-5-甲基苯甲酰基)-4-(环丙基氨基羰基)苯磺酰胺,
和/或一种由以下的通式定义的化合物:
通式(IIa)
或通式(IIb)
或通式(IIc)
其中
m代表数值0、1、2、3、4或5,
A1代表以下所示二价杂环基团之一
n代表数值0、1、2、3、4或5,
A2代表任选被C1-C4烷基和/或C1-C4烷氧基羰基和/或C1-C4烯氧基羰基取代的具有1或2个碳原子的烷二基,
R14代表羟基、巯基、氨基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基氨基或二(C1-C4烷基)氨基,
R15代表羟基、巯基、氨基、C1-C7烷氧基、C1-C6烯氧基、C1-C6烯氧基-C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基氨基或二(C1-C4烷基)氨基,
R16代表任选被氟、氯和/或溴取代的C1-C4烷基,
R17代表氢,各自任选被氟、氯和/或溴取代的C1-C6烷基、C2-C6烯基或C2-C6炔基、C1-C4烷氧基-C1-C4烷基、二氧戊环基-C1-C4烷基、呋喃基、呋喃基-C1-C4烷基、噻吩基、噻唑基、哌啶基,或任选被氟、氯和/或溴或者C1-C4烷基取代的苯基,
R18代表氢,各自任选被氟、氯和/或溴取代的C1-C6烷基、C2-C6烯基或C2-C6炔基、C1-C4烷氧基-C1-C4烷基、二氧戊环基-C1-C4烷基、呋喃基、呋喃基-C1-C4烷基、噻吩基、噻唑基、哌啶基,或任选被氟、氯和/或溴或者C1-C4烷基取代的苯基,
R17和R18还一起代表各自任选被C1-C4烷基、苯基、呋喃基、稠合苯环取代或被两个与其所连接的C原子一起形成一个5元或6元碳环的取代基取代的C3-C6烷二基或C2-C5氧杂烷二基,
R19代表氢、氰基、卤素,或者代表各自任选被氟、氯和/或溴取代的C1-C4烷基、C3-C6环烷基或苯基,
R20代表氢,各自任选被羟基、氰基、卤素或C1-C4烷氧基取代的C1-C6烷基、C3-C6环烷基或三(C1-C4烷基)甲硅烷基,
R21代表氢、氰基、卤素,或者代表各自任选被氟、氯和/或溴取代的C1-C4烷基、C3-C6环烷基或苯基,
X1代表硝基、氰基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基,
X2代表氢、氰基、硝基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基,
X3代表氢、氰基、硝基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基,
和/或由以下通式定义的化合物:
通式(IId)
或通式(IIe)
其中
t代表数值0、1、2、3、4或5,
v代表数值0、1、2、3、4或5,
R22代表氢或C1-C4烷基,
R23代表氢或C1-C4烷基,
R24代表氢,各自任选被氰基、卤素或C1-C4烷氧基取代的C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基氨基或二(C1-C4烷基)氨基,或者各自任选被氰基、卤素或C1-C4烷基取代的C3-C6环烷基、C3-C6环烷基氧基、C3-C6环烷基硫基或C3-C6环烷基氨基,
R25代表氢,任选被氰基、羟基、卤素或C1-C4烷氧基取代的C1-C6烷基,各自任选被氰基或卤素取代的C3-C6烯基或C3-C6炔基,或任选被氰基、卤素或C1-C4烷基取代的C3-C6环烷基,
R26代表氢,任选被氰基、羟基、卤素或C1-C4烷氧基取代的C1-C6烷基,各自任选被氰基或卤素取代的C3-C6烯基或C3-C6炔基,任选被氰基、卤素或C1-C4烷基取代的C3-C6环烷基,或者任选被硝基、氰基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基取代的苯基,或者与R25一起代表各自任选被C1-C4烷基取代的C2-C6烷二基或C2-C5氧杂烷二基,
X4代表硝基、氰基、羧基、氨基甲酰基、甲酰基、氨磺酰基、羟基、氨基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基,并且
X5代表硝基、氰基、羧基、氨基甲酰基、甲酰基、氨磺酰基、羟基、氨基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基。
式(I)提供了本发明化合物的一般定义。以上及以下提及的式中所列基团的优选取代基或范围说明如下:
X优选代表甲基
并且
Y优选代表甲基或乙基
或者
X和Y都优选代表乙基,
A优选代表氢或者各自任选被卤素取代的C1-C12烷基、C3-C8烯基、C1-C10烷氧基-C1-C8烷基、C1-C10烷硫基-C1-C6烷基,任选被卤素、C1-C6烷基或C1-C6烷氧基取代的C3-C8环烷基,所环烷基中任选一个或两个不直接相邻的环成员被氧和/或硫替代,
B优选代表氢、C1-C12烷基或C1-C8烷氧基-C1-C6烷基,或者
A、B与它们所连接的碳原子一起优选代表饱和C3-C10环烷基或不饱和C5-C10环烷基,所述环烷基中任选地一个环成员被氧或硫替代并且该环烷基任选被C1-C8烷基、C1-C8卤代烷基或C1-C8烷氧基单取代或二取代,或者
A、B与它们所连接的碳原子一起优选代表C3-C6环烷基,所述环烷基被任选地由C1-C4烷基取代并任选含有一或两个不直接相邻的氧和/或硫原子的烷撑二基(alkylenediyl)基团取代,或者被与所连接的碳原子一起形成另一个五元至八元环的烷撑二氧基(alkylenedioxyl)基团或烷撑二硫基(alkylenedithioyl)基团取代,或者
A、B与它们所连接的碳原子一起优选代表C3-C8环烷基或C5-C8环烯基,其中两个取代基与它们所连接的碳原子一起代表各自任选被C1-C6烷基、C1-C6烷氧基或卤素取代并且其中任选地一个亚甲基被氧或硫替代的C2-C6烷二基(alkanediyl)、C2-C6烯二基(alkenediyl)或C4-C6烷二烯二基(alkanedienediyl),
A和Q1一起优选代表C2-C6烷二基或C2-C6烯二基,其各自任选被选自卤素、羟基、C1-C10烷基、C1-C6烷氧基、C1-C6烷硫基、C3-C7环烷基、苄氧基或苯基的相同或不同取代基单取代或二取代,所述C1-C10烷基、C1-C6烷氧基、C1-C6烷硫基、C3-C7环烷基各自任选被相同或不同的卤素单取代至三取代,所述苄氧基或苯基各自任选被相同或不同的卤素、C1-C6烷基或C1-C6烷氧基单取代至三取代;其中每一个C2-C6烷二基和C2-C6烯二基基团还任选含有以下基团之一
或者通过C1-C2烷二基基团桥接或者被一个氧原子间隔或桥接,
Q1和Q2相互独立地优选代表氢或C1-C4烷基,
或者
X优选代表乙基
并且
Y优选代表甲基,并且
a)A、B与它们所连接的碳原子一起优选代表饱和的C4-C8环烷基或不饱和的C5-C8环烷基,所述环烷基中任选地一个环成员被氧或硫替代,并且所述环烷基任选被C1-C8烷基、C1-C8卤代烷基或C1-C8烷氧基单取代或二取代,或者
A、B与它们所连接的碳原子一起优选代表C3-C6环烷基,所述环烷基被任选地由C1-C4烷基取代并任选含有一或两个不直接相邻的氧和/或硫原子的烷撑二基基团取代,或者被与所连接的碳原子一起形成另一个五元至八元环的烷撑二氧基基团或烷撑二硫基基团取代,或者
A、B与它们所连接的碳原子一起优选代表C3-C8环烷基或C5-C8环烯基,其中两个取代基与它们所连接的碳原子一起代表各自任选被C1-C6烷基、C1-C6烷氧基或卤素取代并且其中任选地一个亚甲基被氧或硫替代的C2-C6烷二基、C2-C6烯二基或C4-C6烷二烯二基,
Q1和Q2优选代表氢,或者
b)A和Q1一起优选代表C2-C6烷二基或C2-C6烯二基,其各自任选被选自卤素、羟基、C1-C10烷基、C1-C6烷氧基、C1-C6烷硫基、C3-C7环烷基、苄氧基或苯基的相同或不同取代基单取代或二取代,所述C1-C10烷基、C1-C6烷氧基、C1-C6烷硫基、C3-C7环烷基各自任选被相同或不同的卤素单取代至三取代,所述苄氧基或苯基各自任选被相同或不同的卤素、C1-C6烷基或C1-C6烷氧基单取代至三取代;其中每一个C2-C6烷二基和C2-C6烯二基基团还任选含有以下基团之一
或者通过一个C1-C2烷二基基团桥接或者被一个氧原子间隔或桥接,B和Q2相互独立地优选代表氢或C1-C2烷基,
G优选代表氢(a)或代表以下基团之一
其中
E代表一种金属离子等价物或一种铵离子,
L代表氧或硫,并且
M代表氧或硫,
R1优选代表各自任选被卤素取代的C1-C20烷基、C2-C20烯基、C1-C8烷氧基-C1-C8烷基、C1-C8烷硫基-C1-C8烷基、多C1-C8烷氧基-C1-C8烷基,或者任选被卤素、C1-C6烷基或C1-C6烷氧基取代的C3-C8环烷基,所述环烷基中任选一个或多个(优选不多于两个)不直接相邻的环成员被氧和/或硫替代,
代表任选被卤素、氰基、硝基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基或C1-C6烷基磺酰基取代的苯基,
代表任选被卤素、硝基、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基或C1-C6卤代烷氧基取代的苯基-C1-C6烷基,
代表任选被卤素或C1-C6烷基取代的5元或6元杂芳基(例如吡唑基、噻唑基、吡啶基、嘧啶基、呋喃基或噻吩基),
代表任选被卤素或C1-C6烷基取代的苯氧基-C1-C6烷基,或者
代表任选被卤素、氨基或C1-C6烷基取代的5元或6元杂芳氧基-C1-C6烷基(例如吡啶氧基-C1-C6烷基、嘧啶氧基-C1-C6烷基或噻唑氧基-C1-C6烷基),
R2优选代表各自任选被卤素取代的C1-C20烷基、C2-C20烯基、C1-C8烷氧基-C2-C8烷基、多-C1-C8烷氧基-C2-C8烷基,
代表任选被卤素、C1-C6烷基或C1-C6烷氧基取代的C3-C8环烷基,或者
代表各自任选被卤素、氰基、硝基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基或C1-C6卤代烷氧基取代的苯基或苄基,
R3优选代表任选被卤素取代的C1-C8烷基,或者代表各自任选被卤素、C1-C6烷基、C1-C6烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基、氰基或硝基取代的苯基或苄基,
R4和R5相互独立地优选代表各自任选被卤素取代的C1-C8烷基、C1-C8烷氧基、C1-C8烷基氨基、二(C1-C8烷基)氨基、C1-C8烷硫基、C2-C8烯硫基、C3-C7环烷基硫基,或者代表各自任选被卤素、硝基、氰基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、C1-C4烷基或C1-C4卤代烷基取代的苯基、苯氧基或苯硫基,
R6和R7相互独立地优选代表氢,代表各自任选被卤素取代的C1-C8烷基、C3-C8环烷基、C1-C8烷氧基、C3-C8烯基、C1-C8烷氧基-C1-C8烷基,代表任选被卤素、C1-C8卤代烷基、C1-C8烷基或C1-C8烷氧基取代的苯基,任选被卤素、C1-C8烷基、C1-C8卤代烷基或C1-C8烷氧基取代的苄基,或一起代表任选被C1-C4烷基取代并且其中任选地一个碳原子被氧或硫替代的C3-C6亚烷基基团,
R13优选代表氢,代表各自任选被卤素取代的C1-C8烷基、C1-C8烷氧基或C3-C8烯氧基,代表任选被卤素、C1-C4烷基或C1-C4烷氧基取代并且其中任选地一个亚甲基被氧或硫替代的C3-C8环烷基,或者代表各自任选被卤素、C1-C6烷基、C1-C6烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基、硝基或氰基取代的苯基、杂芳基、苯基-C1-C4烷基、苯基-C1-C4烷氧基或杂芳基-C1-C4烷氧基,
R14a优选代表氢或C1-C8烷基,或者
R13和R14a一起优选代表C4-C6烷二基,
R15a和R16a可相同或不同并且优选代表C1-C6烷基,或者
R15a和R16a一起优选代表任选被C1-C6烷基、C1-C6卤代烷基或者任选由卤素、C1-C6烷基、C1-C4卤代烷基、C1-C6烷氧基、C1-C4卤代烷氧基、硝基或氰基取代的苯基取代的C2-C4烷二基,
R17a和R18a相互独立地优选代表氢,代表任选被卤素取代的C1-C8烷基,或代表任选被卤素、C1-C6烷基、C1-C6烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基、硝基或氰基取代的苯基,或者
R17a和R18a与它们所连接的碳原子一起优选代表羰基,或代表任选被卤素、C1-C4烷基或C1-C4烷氧基取代并且其中任选地一个亚甲基被氧或硫替代的C5-C7环烷基,
R19a和R20a相互独立地优选代表C1-C10烷基、C2-C10烯基、C1-C10烷氧基、C1-C10烷基氨基、C3-C10烯基氨基、二(C1-C10烷基)氨基或二(C3-C10烯基)氨基。
在提及的优选的基团定义中,卤素代表氟、氯、溴和碘,特别是氟、氯和溴。
X特别优选代表甲基,
Y特别优选代表甲基或乙基
或者
X和Y都特别优选代表乙基,
A特别优选代表氢,代表各自任选被氟或氯单取代至三取代的C1-C6烷基、C1-C4烷氧基-C1-C2烷基,或者代表任选被C1-C2烷基或C1-C2烷氧基单取代或二取代的C3-C6环烷基,
B特别优选代表氢、C1-C4烷基或C1-C2烷氧基-C1-C2烷基,或者
A、B与它们所连接的碳原子一起特别优选代表饱和或不饱和的C5-C7环烷基,所述环烷基中任选一个环成员被氧或硫替代并且所述环烷基任选被C1-C6烷基、三氟甲基或C1-C6烷氧基单取代或二取代,
A、B与它们所连接的碳原子一起特别优选代表C5-C6环烷基,所述环烷基被任选由甲基或乙基取代并任选含有一个或两个不直接相邻的氧和/或硫原子的烷撑二基基团取代,或者被与所连接的碳原子一起形成另一个五元或六元环的烷撑二氧基基团或烷撑二硫基基团取代,
A、B与它们所连接的碳原子一起特别优选代表C3-C6环烷基或C5-C6环烯基,其中两个取代基与它们所连接的碳原子一起代表各自任选被C1-C2烷基或C1-C2烷氧基取代的C2-C4烷二基、C2-C4烯二基或丁二烯二基,
A和Q1一起特别优选代表C3-C4烷二基或C3-C4烯二基,其各自任选被选自羟基、C1-C2烷基和C1-C2烷氧基的相同或不同的取代基单取代或二取代并且其任选含有以下基团之一
或者可被一个氧原子间隔或桥接,
Q1和Q2相互独立地特别优选代表氢或C1-C2烷基
或者
X特别优选代表乙基
并且
Y特别优选代表甲基
并且
a)A、B与它们所连接的碳原子一起特别优选代表饱和或不饱和的C5-C7环烷基,所述环烷基中任选一个环成员被氧或硫替代并且所述环烷基任选被C1-C6烷基、三氟甲基或C1-C6烷氧基单取代或二取代,条件是此情况下Q3特别优选代表氢或甲基,或者
A、B与它们所连接的碳原子一起特别优选代表C5-C6环烷基,所述环烷基被任选由甲基或乙基取代并任选含有一个或两个不直接相邻的氧和/或硫原子的烷撑二基基团取代,或者被与所连接的碳原子一起形成另一五元或六元环的烷撑二氧基基团或烷撑二硫基基团取代,条件是此情况下Q3特别优选代表氢或甲基,
A、B与它们所连接的碳原子一起特别优选代表C3-C6环烷基或C5-C6环烯基,其中两个取代基与它们所连接的碳原子一起代表各自任选被C1-C2烷基或C1-C2烷氧基取代的C2-C4烷二基、C2-C4烯二基或丁二烯二基,条件是此情况下Q3特别优选代表氢或甲基,或者
Q1和Q2特别优选代表氢
或者
b)A和Q1一起特别优选代表C3-C4烷二基或C3-C4烯二基,其各自任选被选自羟基、C1-C2烷基和C1-C12烷氧基的相同或不同的取代基单取代或二取代并且其任选含有以下基团之一
或者被一个氧原子间隔或桥接,
B和Q2相互独立地特别优选代表氢或甲基,
G特别优选代表氢(a)或代表以下基团之一
其中
E代表一种金属离子等价物或一种铵离子,
L代表氧或硫,并且
M代表氧或硫,
R1特别优选代表各自任选被氟或氯单取代至三取代的C1-C8烷基、C2-C8烯基、C1-C4烷氧基-C1-C2烷基、C1-C4烷硫基-C1-C2烷基,或者代表任选被氟、氯、C1-C2烷基或C1-C2烷氧基单取代或二取代并且其中任选地一个或两个不直接相邻的环成员被氧替代的C3-C6环烷基,
代表任选被氟、氯、溴、氰基、硝基、C1-C4烷基、C1-C4烷氧基、C1-C2卤代烷基或C1-C2卤代烷氧基单取代或二取代的苯基,
R2特别优选代表各自任选被氟单取代至三取代的C1-C8烷基、C2-C8烯基或C1-C4烷氧基-C2-C4烷基,
代表任选被C1-C2烷基或C1-C2烷氧基单取代的C3-C6环烷基,或者
代表各自任选被氟、氯、溴、氰基、硝基、C1-C4烷基、C1-C3烷氧基、三氟甲基或三氟甲氧基单取代或二取代的苯基或苄基,
R3特别优选代表任选被氟单取代至三取代的C1-C6烷基,或者代表任选被氟、氯、溴、C1-C4烷基、C1-C4烷氧基、三氟甲基、三氟甲氧基、氰基或硝基单取代的苯基,
R4特别优选代表各自任选被氟或氯单取代至三取代的C1-C6烷基、C1-C6烷氧基、C1-C6烷基氨基、二(C1-C6烷基)氨基、C1-C6烷硫基、C3-C4烯硫基、C3-C6环烷基硫基,或者代表各自任选被氟、氯、溴、硝基、氰基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、C1-C3烷基或三氟甲基单取代的苯基、苯氧基或苯硫基,
R5特别优选代表任选被氯单取代的C1-C6烷氧基或C1-C6烷硫基,
R6特别优选代表氢、C1-C6烷基、C3-C6环烷基、C1-C6烷氧基、C3-C6烯基、C1-C6烷氧基-C1-C4烷基,代表任选被氟、氯、溴、三氟甲基、C1-C4烷基或C1-C4烷氧基单取代的苯基,代表任选被氟、氯、溴、C1-C4烷基、三氟甲基或C1-C4烷氧基单取代的苄基,
R7特别优选代表C1-C6烷基、C3-C6烯基或C1-C6烷氧基-C1-C4烷基,
R6和R7特别优选一起代表任选被甲基或乙基取代并且其中任选地一个亚甲基被氧或硫替代的C4-C5亚烷基,
R13特别优选代表氢,代表各自任选被氟或氯单取代至三取代的C1-C8烷基、C1-C8烷氧基、C3-C6烯氧基,代表任选被卤素、C1-C4烷基或C1-C4烷氧基取代并且其中任选地一个亚甲基被氧或硫替代的C3-C8环烷基,或者代表各自任选被氟、氯、溴、C1-C4烷基、C1-C4烷氧基、C1-C2卤代烷基、C1-C2卤代烷氧基、硝基或氰基取代的苯基、吡啶基、嘧啶基、噻唑基、苯基-C1-C2烷基或吡啶基-C1-C2烷氧基,
R17a和R18a相互独立地特别优选代表氢,代表任选被氟或氯单取代至三取代的C1-C4烷基,或者代表任选被氟、氯、溴、C1-C4烷基、C1-C4烷氧基、C1-C2卤代烷基、C1-C2卤代烷氧基、硝基或氰基单取代或二取代的苯基,或者
R17a和R18a与它们所连接的碳原子一起特别优选代表羰基,或代表任选被氟、氯、C1-C3烷基或C1-C4烷氧基单取代或二取代的C5-C6环烷基。
在提及的特别优选的基团定义中,卤素代表氟、氯和溴,特别是氟和氯。
X非常特别优选代表甲基,
Y非常特别优选代表甲基或乙基
或者
X和Y都非常特别优选代表乙基,
A非常特别优选代表氢,代表各自任选被氟单取代至三取代的C1-C4烷基或C1-C2烷氧基-C1-C2烷基,代表环丙基、环戊基或环己基,
B非常特别优选代表氢、甲基或乙基,或者
A、B与它们所连接的碳原子一起非常特别优选代表饱和C5-C6环烷基,所述环烷基中任选地一个环成员被氧替代并且所述环烷基任选被甲基、乙基、丙基、异丙基、三氟甲基、甲氧基、乙氧基、丙氧基或丁氧基单取代,
A、B与它们所连接的碳原子一起非常特别优选代表被烷撑二氧基取代的C6-环烷基,所述烷撑二氧基含有两个不直接相邻的氧原子并且与其所连接的碳原子一起形成另一五元或六元环,
A、B与它们所连接的碳原子一起非常特别优选代表C5-C6环烷基或C5-C6环烯基,其中两个取代基与它们所连接的碳原子一起代表C2-C4烷二基或C2-C4烯二基或丁二烯二基,
A和Q1一起非常特别优选代表C3-C4烷二基或C3-C4烯二基,其各自任选被选自羟基、甲基和甲氧基的相同或不同的取代基单取代或二取代并且其任选含有以下基团之一
或可被氧原子间隔或桥接,
Q1和Q2相互独立地非常特别优选代表氢或甲基
或者
X非常特别优选代表乙基
并且
Y非常特别优选代表甲基
并且
a)A、B与它们所连接的碳原子一起非常特别优选代表饱和C5-C6环烷基,所述环烷基中任选地一个环成员被氧或硫替代并且所述环烷基任选被甲基、乙基、丙基、异丙基、三氟甲基、甲氧基、乙氧基、丙氧基或丁氧基单取代,
A、B与它们所连接的碳原子一起非常特别优选代表被烷撑二氧基取代的C6-环烷基,所述烷撑二氧基含有两个不直接相邻的氧原子并且与其所连接的碳原子一起形成另一五元或六元环,
A、B与它们所连接的碳原子一起非常特别优选代表C5-C6环烷基或C5-C6环烯基,其中两个取代基与它们所连接的碳原子一起代表C2-C4烷二基或C2-C4烯二基或丁二烯二基,
Q1和Q2非常特别优选代表氢
或者
b)A和Q1一起非常特别优选代表C3-C4烷二基或C3-C4烯二基,其各自任选被选自羟基、甲基和甲氧基的相同或不同的取代基单取代或二取代并且其任选含有以下基团之一
或被一个氧原子间隔或桥接,
B和Q2非常特别优选相互独立地代表氢或甲基,
G非常特别优选代表氢(a)或代表以下基团之一
其中
E代表一种铵离子,
L代表氧或硫,并且
M代表氧或硫,
R1非常特别优选代表C1-C6烷基、C2-C6烯基、C1-C2烷氧基-C1烷基、C1-C2烷硫基-C1烷基,或者代表任选被氟、氯、甲基或甲氧基单取代的C3-C6环丙基,或者代表被氯单取代的C1-C4烷基,
代表任选被氟、氯、溴、氰基、硝基、甲基、甲氧基、三氟甲基或三氟甲氧基单取代的苯基,
R2非常特别优选代表各自任选被氟单取代至三取代的C1-C8烷基、C2-C6烯基或C1-C4烷氧基-C2-C3烷基、苯基或苄基,
R3非常特别优选代表C1-C6烷基,
R4非常特别优选代表各自任选被氟或氯单取代至三取代的C1-C4烷基、C1-C4烷氧基、C1-C4烷基氨基、二(C1-C4烷基)氨基、C1-C4烷硫基、C3-C4烯硫基、C3-C6环烷基硫基,或者代表各自任选被氟、氯、溴、硝基、氰基、甲氧基、三氟甲氧基、甲硫基、三氟甲硫基、甲基或三氟甲基单取代的苯基、苯氧基或苯硫基,
R5非常特别优选代表任选被氯单取代的C1-C4烷氧基或C1-C4烷硫基,
R13非常特别优选代表各自任选被氟或氯单取代至三取代的C1-C4烷基、C1-C4烷氧基或C3-C4烯氧基,或者代表各自任选被氟、氯、溴、甲基、甲氧基、三氟甲基或三氟甲氧基取代的苄基或吡啶基,
R17a和R18a相互独立地非常特别优选代表任选被氟或氯单取代至三取代的C1-C4烷基,或者代表任选被氟、氯、溴、甲基、甲氧基、三氟甲基、三氟甲氧基、硝基或氰基单取代或二取代的苯基,或者
R17a和R18a与它们所连接的碳原子一起非常特别优选代表任选被甲基或乙基单取代或二取代的C5-C6环烷基。
X最优选代表甲基,
Y最优选代表甲基或乙基
或者
X和Y都最优选代表乙基,
A最优选代表甲基,
B最优选代表氢或甲基,或者
A、B与它们所连接的碳原子一起最优选代表饱和C5-C6环烷基,所述环烷基中任选地一个环成员被氧替代并且所述环烷基任选被甲基单取代,
A和Q1一起最优选代表C3-C5烷二基或C3-C5烯二基,其各自任选被甲基单取代,
其任选含有以下基团之一
Q1和Q2最优选代表氢,
或者
X最优选代表乙基
并且
Y最优选代表甲基
并且
a)A、B与它们所连接的碳原子一起最优选代表其中任选地一个环成员被氧替代的饱和C5-C6环烷基,
Q1和Q2最优选代表氢
或者
b)A和Q1一起最优选代表C3-C5烷二基或C3-C5烯二基,其各自任选被甲基单取代,
其任选含有以下基团之一
或被一个氧原子间隔或桥接,
B和Q2最优选代表氢,
G最优选代表氢(a)或代表以下基团之一
其中
L代表氧,并且
M代表氧,
R1最优选代表C1-C6烷基、C1-C2烷氧基-C1-C2烷基,或者代表被氯单取代的C1-C4烷基,
R2最优选代表C1-C8烷基,
R4最优选代表任选被氯单取代的C1-C4烷氧基,
R5最优选代表任选被氯单取代的C1-C4烷氧基,
R17a和R18a最优选代表甲基。
尤其优选的是式(I’)的纯异构体化合物
其中
X和Y相互独立地代表甲基或乙基,
并且
G代表非常特别优选的基团,
1'-顺式 1'-反式
其中特别强调反式化合物。
以上所列的一般或优选的基团定义可按照需要相互结合,即包括各自的范围和优选范围之间的结合。它们既适用于终产物也相应地适用于前体和中间体。
本发明优选含有以上所列优选(优选的)含义的组合的式(I)化合物。
本发明特别优选含有以上所列特别优选含义的组合的式(I)化合物。
本发明非常特别优选含有以上所列非常特别优选含义的组合的式(I)化合物。
本发明最优选含有以上所列最优选含义的组合的式(I)化合物。
饱和或不饱和烃基团,例如烷基、烷二基或烯基,只要可能,各自可为直链或支链的,也包括与杂原子的结合,例如烷氧基。
除非另外指明,任选被取代的基团可被单取代或多取代,并且在多个取代基的情况下取代基可以相同或不同。
除实施例中提及的化合物外,可具体提及以下式(I-1-a)的化合物:
表1:X=CH3,Y=CH3,Q2=H
表2:X=C2H5,Y=C2H5,Q2=H
表3:X=C2H5,Y=CH3,Q2=H
以上所列有关改进作物植物相容性的式(IIa)、(IIb)、(IIc)、(IId)和(IIe)的化合物的基团的优选含义在下面进行定义。
m优选代表数值0、1、2、3或4。
A1优选代表以下所示的二价杂环基团之一
n优选代表数值0、1、2、3或4。
A2优选代表各自任选被甲基、乙基、甲氧基羰基、乙氧基羰基或烷氧基羰基取代的亚甲基或亚乙基。
R14优选代表羟基、巯基、氨基、甲氧基、乙氧基、正丙基或异丙基、正丁氧基、异丁氧基、仲丁氧基或叔丁氧基、甲硫基、乙硫基、正丙硫基或异丙硫基、正丁硫基、异丁硫基、仲丁硫基或叔丁硫基、甲氨基、乙氨基、正丙氨基或异丙氨基、正丁氨基、异丁氨基、仲丁氨基或叔丁氨基、二甲氨基或二乙氨基。
R15优选代表羟基、巯基、氨基、甲氧基、乙氧基、正丙氧基或异丙氧基、正丁氧基、异丁氧基、仲丁氧基或叔丁氧基、1-甲基己基氧基、烯丙氧基、1-烯丙氧基甲基乙氧基、甲硫基、乙硫基、正丙硫基或异丙硫基、正丁硫基、异丁硫基、仲丁硫基或叔丁硫基、甲氨基、乙氨基、正丙氨基或异丙氨基、正丁氨基、异丁氨基、仲丁氨基或叔丁氨基、二甲氨基或二乙氨基。
R16优选代表各自任选被氟、氯和/或溴取代的甲基、乙基、正丙基或异丙基。
R17优选代表氢,各自任选被氟和/或氯取代的甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、丙烯基、丁烯基、丙炔基或丁炔基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、二氧戊环基甲基、呋喃基、呋喃基甲基、噻吩基、噻唑基、哌啶基,或任选被氟、氯、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基取代的苯基。
R18优选代表氢,各自任选被氟和/或氯取代的甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、丙烯基、丁烯基、丙炔基或丁炔基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、二氧戊环基甲基、呋喃基、呋喃基甲基、噻吩基、噻唑基、哌啶基,或任选被氟、氯、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基取代的苯基,或与R17一起代表任选被甲基、乙基、呋喃基、苯基、稠合苯环或被两个取代基取代的基团-CH2-O-CH2-CH2-和-CH2-CH2-O-CH2-CH2-中的一个,所述两个取代基与它们所连接的C原子一起形成一个5元或6元碳环。
R19优选代表氢、氰基、氟、氯、溴,或者代表各自任选被氟、氯和/或溴取代的甲基、乙基、正丙基或异丙基、环丙基、环丁基、环戊基、环己基或苯基。
R20优选代表氢,任选被羟基、氰基、氟、氯、甲氧基、乙氧基、正丙氧基或异丙氧基取代的甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基。
R21优选代表氢、氰基、氟、氯、溴,或者代表各自任选被氟、氯和/或溴取代的甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、环丙基、环丁基、环戊基、环己基或苯基。
X1优选代表硝基、氰基、氟、氯、溴、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、二氟甲基、二氯甲基、三氟甲基、三氯甲基、氯二氟甲基、氟二氯甲基、甲氧基、乙氧基、正丙氧基或异丙氧基、二氟甲氧基或三氟甲氧基。
X2优选代表氢、硝基、氰基、氟、氯、溴、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、二氟甲基、二氯甲基、三氟甲基、三氯甲基、氯二氟甲基、氟二氯甲基、甲氧基、乙氧基、正丙氧基或异丙氧基、二氟甲氧基或三氟甲氧基。
X3优选代表氢、硝基、氰基、氟、氯、溴、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、二氟甲基、二氯甲基、三氟甲基、三氯甲基、氯二氟甲基、氟二氯甲基、甲氧基、乙氧基、正丙氧基或异丙氧基、二氟甲氧基或三氟甲氧基。
t优选代表数值0、1、2、3或4。
v优选代表数值0、1、2、3或4。
R22优选代表氢、甲基、乙基、正丙基或异丙基。
R23优选代表氢、甲基、乙基、正丙基或异丙基。
R24优选代表氢,各自任选被氰基、氟、氯、甲氧基、乙氧基、正丙氧基或异丙氧基取代的甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、甲氧基、乙氧基、正丙氧基或异丙氧基、正丁氧基、异丁氧基、仲丁氧基或叔丁氧基、甲硫基、乙硫基、正丙硫基或异丙硫基、正丁硫基、异丁硫基、仲丁硫基或叔丁硫基、甲氨基、乙氨基、正丙氨基或异丙氨基、正丁氨基、异丁氨基、仲丁氨基或叔丁氨基、二甲氨基或二乙氨基,或者各自任选被氰基、氟、氯、溴、甲基、乙基、正丙基或异丙基取代的环丙基、环丁基、环戊基、环己基、环丙基氧基、环丁基氧基、环戊基氧基、环己基氧基、环丙基硫基、环丁基硫基、环戊基硫基、环己基硫基、环丙基氨基、环丁基氨基、环戊基氨基或环己基氨基。
R25优选代表氢,各自任选被氰基、羟基、氟、氯、甲氧基、乙氧基、正丙氧基或异丙氧基取代的甲基、乙基、正丙基或异丙基、正丁基、异丁基或仲丁基,各自任选被氰基、氟、氯或溴取代的丙烯基、丁烯基、丙炔基或丁炔基,或者各自任选被氰基、氟、氯、溴、甲基、乙基、正丙基或异丙基取代的环丙基、环丁基、环戊基或环己基。
R26优选代表氢,各自任选被氰基、羟基、氟、氯、甲氧基、乙氧基、正丙氧基或异丙氧基取代的甲基、乙基、正丙基或异丙基、正丁基、异丁基或仲丁基,各自任选被氰基、氟、氯或溴取代的丙烯基、丁烯基、丙炔基或丁炔基,或者各自任选被氰基、氟、氯、溴、甲基、乙基、正丙基或异丙基取代的环丙基、环丁基、环戊基或环己基,或者任选被硝基、氰基、氟、氯、溴、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、三氟甲基、甲氧基、乙氧基、正丙氧基或异丙氧基、二氟甲氧基或三氟甲氧基取代的苯基,或与R25一起代表各自任选被甲基或乙基取代的丁烷-1,4-二基(三亚甲基)、戊烷-1,5-二基、1-氧杂丁烷-1,4-二基或3-氧杂戊烷-1,5-二基。
X4优选代表硝基、氰基、羧基、氨基甲酰基、甲酰基、氨磺酰基、羟基、氨基、氟、氯、溴、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、三氟甲基、甲氧基、乙氧基、正丙氧基或异丙氧基、二氟甲氧基或三氟甲氧基。
X5优选代表硝基、氰基、羧基、氨基甲酰基、甲酰基、氨磺酰基、羟基、氨基、氟、氯、溴、甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、三氟甲基、甲氧基、乙氧基、正丙氧基或异丙氧基、二氟甲氧基或三氟甲氧基。
本发明非常特别优选为除草剂安全剂的式(IIa)化合物的实例列于下表中。
表:式(IIa)化合物的实例
本发明非常特别优选为除草剂安全剂的式(IIb)化合物的实例列于下表中。
表:式(IIb)化合物的实例
本发明非常特别优选为除草剂安全剂的式(IIc)化合物的实例列于下表中。
表:式(IIc)化合物的实例
本发明非常特别优选为除草剂安全剂的式(IId)化合物的实例列于下表中。
表:式(IId)化合物的实例
本发明非常特别优选为除草剂安全剂的式(IIe)化合物的实例列于下表中。
表:式(IIe)化合物的实例
最优选的改进作物植物相容性的化合物[组分(b')]为解草酯、解草唑、双苯噁唑酸、吡唑解草酯、解草恶唑、解草啶、苄草隆、杀草隆、哌草丹和化合物IIe-5和IIe-11,并且特别强调解草酯和吡唑解草酯。
本发明的各自含有一种式(I)活性化合物和一种以上定义的安全剂的选择性除草结合物的实例列于下表中。
式(I)的活性化合物 | 安全剂 |
I-a | 解草酯 |
I-a | 解草唑 |
I-a | 双苯噁唑酸 |
I-a | 吡唑解草酯 |
I-a | 解草恶唑 |
I-a | 解草啶 |
I-a | 苄草隆 |
I-a | 杀草隆 |
I-a | 哌草丹 |
I-a | IIe-11 |
I-a | IIe-5 |
I-b | 解草酯 |
I-b | 解草唑 |
I-b | 双苯噁唑酸 |
I-b | 吡唑解草酯 |
I-b | 解草恶唑 |
I-b | 解草啶 |
I-b | 苄草隆 |
I-b | 杀草隆 |
式(I)的活性化合物 | 安全剂 |
I-b | 哌草丹 |
I-b | IIe-11 |
I-b | IIe-5 |
I-c | 解草酯 |
I-c | 解草唑 |
I-c | 双苯噁唑酸 |
I-c | 吡唑解草酯 |
I-c | 解草恶唑 |
I-c | 解草啶 |
I-c | 苄草隆 |
I-c | 杀草隆 |
I-c | 哌草丹 |
I-c | IIe-11 |
I-c | IIe-5 |
I-d | 解草酯 |
I-d | 解草唑 |
I-d | 双苯噁唑酸 |
I-d | 吡唑解草酯 |
I-d | 解草恶唑 |
I-d | 解草啶 |
I-d | 苄草隆 |
I-d | 杀草隆 |
I-d | 哌草丹 |
I-d | IIe-11 |
I-d | IIe-5 |
I-e | 解草酯 |
I-e | 解草唑 |
I-e | 双苯噁唑酸 |
I-e | 吡唑解草酯 |
I-e | 解草恶唑 |
式(I)的活性化合物 | 安全剂 |
I-e | 解草啶 |
I-e | 苄草隆 |
I-e | 杀草隆 |
I-e | 哌草丹 |
I-e | IIe-11 |
I-e | IIe-5 |
I-f | 解草酯 |
I-f | 解草唑 |
I-f | 双苯噁唑酸 |
I-f | 吡唑解草酯 |
I-f | 解草恶唑 |
I-f | 解草啶 |
I-f | 苄草隆 |
I-f | 杀草隆 |
I-f | 哌草丹 |
I-f | IIe-5 |
I-f | IIe-11 |
I-g | 解草酯 |
I-g | 解草唑 |
I-g | 双苯噁唑酸 |
I-g | 吡唑解草酯 |
I-g | 解草恶唑 |
I-g | 解草啶 |
I-g | 苄草隆 |
I-g | 杀草隆 |
I-g | 哌草丹 |
I-g | IIe-5 |
I-g | IIe-11 |
本发明用作安全剂的通式(II-a)的化合物是已知的,并且/或者可通过本身已知方法制备(参见WO-A-91/07874、WO-A-95/07897)。
本发明用作安全剂的通式(II-b)的化合物是已知的,并且/或者可通过本身已知方法制备(参见EP-A-191736)。
本发明用作安全剂的通式(II-c)的化合物是已知的,并且/或者可通过本身已知方法制备(参见DE-A-2218097、DE-A-2350547)。
本发明用作安全剂的通式(II-d)的化合物是已知的,并且/或者可通过本身已知方法制备(参见DE-A-19621522/US-A-6235680)。
本发明用作安全剂的通式(II-e)的化合物是已知的,并且/或者可通过本身已知方法制备(参见WO-A-99/66795/US-A-6251827)。
令人惊讶的是,现已发现以上定义的通式(I)化合物与以上所列组(b')的安全剂(解毒剂)的活性化合物结合物,在具有极好的有用植物耐受性的同时,具有特别高的除草活性并且可在多种作物中,特别是谷类中(尤其是小麦)以及大豆、马铃薯、玉米和稻中,用于选择性防治杂草。
本文中,被认为令人惊讶的是,在许多能够对抗除草剂对作物植物有害影响的已知安全剂或解毒剂中,尤以上述组(b')所列的化合物较为适宜,其几乎完全消除了式(I)化合物对作物植物的有害影响而对除草剂的除草活性却没有大的有害影响。
本文需强调的是组(b')中特别优选的和最优选的混合组分的特别有利的效果,特别是对于谷类植物,例如,小麦、大麦和黑麦,以及玉米和稻等作物植物。
根据方法(A),使用例如5-(2-乙基-4,6-二甲基苯基)-2,3-四亚甲基-4-氧代戊酸乙酯,本发明方法的过程可通过以下反应方案表述:
根据方法(B),使用例如2-(2-乙基-4,6-二甲基苯基)-4,4-二甲基环戊烷-1,3-二酮和新戊酰氯作为原料,本发明方法的过程可通过以下反应方案表述:
根据方法(B),使用例如2-(2,6-二乙基-4-甲基苯基)-4,4-五亚甲基-1,3-二酮和乙酸酐作为原料,本发明方法的过程可通过以下反应方案表述:
根据方法(C),使用例如2-[(2,6-二乙基-4-甲基)苯基]-4,5-四亚甲基环戊烷-1,3-二酮和氯甲酸乙酯作为原料,本发明方法的过程可通过以下反应方案表述:
根据方法(D),使用例如2-[(2,4,6-三乙基苯基]-4,5-四亚甲基环戊烷-1,3-二酮和氯单硫代甲酸甲酯作为原料,本发明方法的过程可通过以下反应方案表述:
根据方法(E),使用例如2-(2,6-二乙基-4-甲基苯基)-5,5-五亚甲基环戊烷-1,3-二酮和甲磺酰氯作为原料,本发明方法的过程可通过以下反应方案表述:
根据方法(F),使用例如2-(2-乙基-4,6-二甲基苯基)-4,4-二甲基环戊烷-1,3-二酮和甲硫代膦酸2,2,2-三氟乙基酯作为原料,本发明方法的过程可通过以下反应方案表述:
根据方法(G),使用例如2-(2-乙基-4,6-二甲基苯基]-4,4-二甲基环戊烷-1,3-二酮和NaOH作为组分,本发明方法的过程可通过以下反应方案表述:
根据方法(H)α,使用例如2-(2-乙基-4,6-二甲基苯基)-4,4-四亚甲基环戊烷-1,3-二酮和异氰酸乙酯作为原料,本发明方法的过程可通过以下反应方案表述:
根据方法(H)β,使用例如2-(2,6-二乙基-4-甲基苯基)-5,5-五亚甲基环戊烷-1,3-二酮和二甲基氨基甲酰氯作为原料,本发明方法的过程可通过以下反应方案表述:
本发明方法(A)中所需原料式(II)化合物是新化合物。
其中
A、B、Q1、Q2、X、Y和R8具有以上给出的含义。
它们可通过原则上已知的方法制备。
式(II)的5-芳基-4-酮甲酸酯,通过例如式(XIII)的5-芳基-4-酮甲酸的酯化(参见,例如Organikum,15版,Berlin,1977,499页)或烷基化(参见制备实施例)获得
其中
X、Y、A、B、Q1和Q2具有以上给出的含义。
式(XIII)的5-芳基-4-酮甲酸是新化合物,但可通过原则上已知的方法制备(WO96/01 798、WO97/14667、WO98/39281、WO01/74770)。
其中
A、B、Q1、Q2、X和Y具有以上给出的含义。
式(XIII)的5-芳基-4-酮甲酸,通过例如式(XIV)的2-苯基-3-氧代己二酸酯的脱羧获得,该反应如果合适在一种稀释剂的存在下并且如果合适在一种碱或一种酸的存在下进行(参见,例如Organikum,15版,Berlin,1977,519-521页)
其中
A、B、Q1、Q2、X和Y具有以上给出的含义,并且
R8和R8'代表烷基(特别是C1-C8烷基),并且
当使用式(XVI)的化合物时,R8代表氢。
式(XIV)的化合物是新化合物
其中
A、B、Q1、Q2、X、Y、R8、R8'具有以上给出的含义,并且
当使用式(XVI)的化合物时,R8代表氢。
式(XIV)的化合物,通过例如式(XV)的二羧酸单酯酰氯(dicarboxylicmonoester chloride)或者式(XVI)的羧酸酐在一种稀释剂的存在下并且在一种碱的存在下,用式(XVII)的苯基乙酸酯酰化获得(参见,例如M.S.Chambers,E.J.Thomas,D.J.Williams,J.Chem.Soc.Chem.Commun.,(1987),1228,另参见制备实施例),
其中
A、B、Q1、Q2和R8具有以上给出的含义,并且
Ha1代表氯或溴,
其中
A、B、Q1和Q2具有以上给出的含义,
其中
X、Y和R8'具有以上给出的含义。
式(XV)和(XVI)的一些化合物为已知的有机化合物,并且/或者它们可通过原则上已知的方法以简单方式进行制备。
此外作为实施本发明方法(B)、(C)、(D)、(E)、(F)、(G)和(H)的其它所需原料的式(III)的酰基卤、式(IV)的羧酸酐、式(V)的氯甲酸酯或氯甲酸硫代酯、式(VI)的氯单硫代甲酸酯或氯二硫代甲酸酯、式(VII)的磺酰氯、式(VIII)的磷化合物、式(IX)和(X)的金属氢氧化物、金属醇盐或胺和式(XI)的异氰酸酯以及式(XII)的氨基甲酰氯是公知的有机或无机化合物。
此外,式(XV)、(XVI)和(XVII)的化合物已知于开篇所引的专利申请和/或可通过其中给出的方法制备。
方法(A)的特征在于将式(II)的化合物——其中A、B、Q1、Q2、X、Y和R8具有以上给出的含义——在一种碱的存在下进行分子内缩合。
本发明方法(A)中使用的适宜的稀释剂为对反应参与物呈惰性的所有有机溶剂。优选使用烃类,例如甲苯和二甲苯;以及醚类,例如二丁醚、四氢呋喃、二噁烷、乙二醇二甲醚和二乙二醇二甲醚;以及极性溶剂,例如二甲基亚砜、环丁砜、二甲基甲酰胺和N-甲基吡咯烷酮。还可使用醇类,例如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇和叔丁醇。
实施本发明方法(B)的适宜碱类(脱质子剂)为所有常规质子受体。优选使用碱金属和碱土金属氧化物、氢氧化物和碳酸盐,例如氢氧化钠、氢氧化钾、氧化镁、氧化钙、碳酸钠、碳酸钾和碳酸钙,它们也可在等摩尔量的相转移催化剂的存在下使用,所述相转移催化剂例如,三乙基苄基氯化铵。但是,也可使用相对较大程度过量(最多至3mol)的一种组分或另一种成分。
方法(B-α)的特征在于式(I-a)的化合物各自与式(III)的酰基卤反应,如果合适在一种稀释剂的存在下并且如果合适在一种酸结合剂的存在下进行。
本发明方法(B-α)中使用的适宜稀释剂为对酰基卤呈惰性的所有溶剂。优选使用烃类,例如汽油、苯、甲苯、二甲苯和1,2,3,4-四氢化萘;以及卤代烃,例如二氯甲烷、三氯甲烷、四氯化碳、氯苯和邻二氯苯;以及酮,例如丙酮和甲基异丙基酮;以及醚,例如乙醚、四氢呋喃和二噁烷;还有羧酸酯,例如乙酸乙酯;以及强极性溶剂,例如二甲基甲酰胺、二甲基亚砜和环丁砜。如果酰基卤对水解足够稳定,该反应也可在水的存在下进行。
用于本发明方法(B-α)的反应的适宜酸结合剂为所有常规的酸受体。优选使用叔胺,例如三乙胺、吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环十一烯(DBU)、二氮杂双环壬烯(DBN)、Hünig碱和N,N-二甲基苯胺,以及碱土金属氧化物,例如氧化镁和氧化钙,以及碱金属和碱土金属的碳酸盐,例如碳酸钠、碳酸钾和碳酸钙,以及碱金属氢氧化物,例如氢氧化钠和氢氧化钾。
本发明方法(B-α)的反应温度可在相对较宽的范围内变化。一般而言,本方法在-20℃和+150℃之间、优选0℃至100℃之间的温度实施。
实施本发明方法(B-α)时,式(I-a)的原料和式(III)的酰基卤通常各自以近似等当量使用。然而,也可使用相对较大程度过量(最多至5mol)的酰基卤。通过常规方法进行后处理。
方法(B-β)的特征在于式(I-a)的化合物与式(IV)的羧酸酐反应,如果合适在一种稀释剂的存在下并且如果合适在一种酸结合剂的存在下进行。
本发明方法(B-β)中使用的适宜稀释剂优选为当使用酰基卤时同样优选的稀释剂。此外,过量的羧酸酐同时可作为稀释剂。
如果需要,方法(B-β)中加入的适宜的酸结合剂优选为当使用酰基卤时同样优选的酸结合剂。
本发明方法(B-β)的反应温度可在相对较宽的范围内变化。一般而言,该方法在-20℃和+150℃之间、优选0℃和100℃之间的温度实施。
当实施本发明方法(B-β)时,式(I-a)的原料和式(IV)的羧酸酐通常各自以近似等当量使用。然而,也可使用相对较大程度过量(最多至5mol)的羧酸酐。通过常规方法进行后处理。
通常,稀释剂和过量的羧酸酐及形成的羧酸通过蒸馏或者通过用有机溶剂或水洗涤而除去。
方法(C)的特征在于式(I-a)的化合物各自与式(V)的氯甲酸酯或氯甲酸硫代酯反应,如果合适在一种稀释剂的存在下并且如果合适在一种酸结合剂的存在下进行。
适用于本发明方法(C)的适宜酸结合剂为所有常规的酸受体。优选使用叔胺,例如三乙胺、吡啶、DABCO、DBU、DBN、Hünig碱和N,N-二甲基苯胺,以及碱土金属氧化物,例如氧化镁和氧化钙,以及碱金属和碱土金属的碳酸盐,例如碳酸钠、碳酸钾和碳酸钙,以及碱金属氢氧化物,例如氢氧化钠和氢氧化钾。
本发明方法(C)中使用的适宜的稀释剂为对氯甲酸酯或氯甲酸硫代酯呈惰性的所有溶剂。优选使用烃类,例如汽油、苯、甲苯、二甲苯和1,2,3,4-四氢化萘;以及卤代烃,例如二氯甲烷、三氯甲烷、四氯化碳、氯苯和邻二氯苯;以及酮,例如丙酮和甲基异丙基酮;以及醚,例如乙醚、四氢呋喃和二噁烷;还有羧酸酯,例如乙酸乙酯;以及强极性溶剂,例如二甲基亚砜和环丁砜。
当实施本发明方法(C)时,反应温度可在相对较宽的范围内变化。如果反应在一种稀释剂和一种酸结合剂的存在下进行,则反应温度通常在-20℃和+100℃之间,优选0℃和50℃之间。
本发明方法(C)通常在大气压力下实施。
当实施本发明方法(C)时,式(I-a)的原料和合适的式(III)的氯甲酸酯或氯甲酸硫代酯通常以近似等当量使用。但是,也可使用相对较大程度过量(最多至2摩尔)的一种组分或另一种组分。通过常规方法进行后处理。通常,将沉淀出的盐除去并将剩余的反应混合物通过在减压下除去稀释剂进行浓缩。
本发明方法(D)的特征在于式(I-a)的化合物在一种稀释剂的存在下,并且如果合适在一种酸结合剂的存在下,各自与式(VI)的化合物反应。
在制备方法(D)中,在0-120℃、优选20℃-60℃,每摩尔式(I-a)的原料使用约1mol的式(VI)的氯单硫代甲酸酯或氯二硫代甲酸酯。
如果需要,适于添加的稀释剂为所有惰性极性有机溶剂,例如醚、酰胺、砜、亚砜以及卤代烷烃。
优选使用二甲基亚砜、四氢呋喃、二甲基甲酰胺或二氯甲烷。
在一个优选的实施方案中,如果化合物(I-a)的烯醇式盐通过添加强脱质子剂例如氢化钠或叔丁醇钾进行制备,则可免除另外加入酸结合剂。
如果使用酸结合剂,则其可为常规的无机碱或有机碱,例如氢氧化钠、碳酸钠、碳酸钾、吡啶、三乙胺。
该反应可在大气压力或提高的压力下进行,并且优选在大气压力下进行。通过常规方法进行后处理。
本发明方法(E)的特征在于式(I-a)的化合物各自与式(VII)的磺酰氯反应,如果合适在一种稀释剂的存在下并且如果合适在一种酸结合剂的存在下进行。
在制备方法(E)中,在-20至150℃、优选0℃至70℃,每摩尔式(I-a)的原料与约1mol的式(VII)的磺酰氯反应。
如果需要,适于添加的稀释剂为所有惰性的极性有机溶剂,例如醚、酰胺、腈、砜、亚砜,或者卤代烃如二氯甲烷。
优选使用二甲基亚砜、四氢呋喃、二甲基甲酰胺、二氯甲烷。
在一个优选的实施方案中,如果式(I-a)的烯醇式盐通过添加强脱质子剂(例如氢化钠或叔丁醇钾)进行制备,则可免除另外添加酸结合剂。
如果使用酸结合剂,则其可为常规的无机碱或有机碱,例如氢氧化钠、碳酸钠、碳酸钾、吡啶和三乙胺。
该反应可在大气压力或在提高的压力下进行,优选在大气压力下进行。通过常规方法进行后处理。
本发明方法(F)的特征在于式(I-a)的化合物各自与式(VIII)的磷化合物反应,如果合适在一种稀释剂的存在下并且如果合适在一种酸结合剂的存在下进行。
在制备方法(F)中,为获得式(I-e)的化合物,在-40℃和150℃之间、优选-10℃和110℃之间,每摩尔式(I-a)的化合物与1-2mol、优选1-1.3mol式(VIII)的磷化合物反应。
如果需要,适于添加的稀释剂为所有惰性的极性有机溶剂,例如醚、酰胺、腈、醇、硫化物、砜、亚砜等。
优选使用乙腈、二甲基亚砜、四氢呋喃、二甲基甲酰胺、二氯甲烷。
如果需要,适于添加的酸结合剂为常规的无机碱或有机碱,例如氢氧化物、碳酸盐或胺。可提及的实例为氢氧化钠、碳酸钠、碳酸钾、吡啶和三乙胺。
该反应可在大气压力或提高的压力下进行,并且优选在大气压力下进行。通过有机化学中的常规方法进行后处理。终产物优选通过结晶、色谱纯化或“减压蒸馏(incipient distillation)”——即在减压下除去挥发性组分——进行纯化。
方法(G)的特征在于式(I-a)的化合物与式(IX)的金属氢氧化物或金属醇盐或式(X)的胺反应,如果合适在一种稀释剂的存在下进行。
本发明方法(G)中使用的适宜稀释剂优选为醚,例如四氢呋喃、二噁烷、乙醚,或醇,例如甲醇、乙醇、异丙醇,以及水。
本发明方法(G)一般在大气压力下进行。
该反应温度一般在-20℃和100℃之间,优选0℃和50℃之间。
本发明方法(H)的特征在于式(I-a)的化合物各自(H-α)与式(XI)的化合物反应,如果合适在一种稀释剂的存在下并且如果合适在一种催化剂的存在下进行;或者(H-β)与式(XII)的化合物反应,如果合适在一种稀释剂的存在下并且如果合适在一种酸结合剂的存在下进行。
在制备方法(H-α)中,在0-100℃之间、优选20-50℃,每摩尔式(I-a)的原料与约1mol式(XI)的异氰酸酯反应。
如果需要,适于添加的稀释剂为所有惰性有机溶剂,例如醚、酰胺、腈、砜、亚砜。
如果合适,可添加催化剂以加速反应。极有利地适于用作催化剂的为有机锡化合物,例如二月桂酸二丁锡。该反应优选在大气压力下进行。
在制备方法(H-β)中,在-20-150℃、优选0-70℃,每摩尔式(I-a)的原料与约1mol的式(XII)的氨基甲酰氯反应。
如果需要,适于添加的稀释剂为所有惰性的极性有机溶剂,例如醚、酰胺、砜、亚砜或卤代烃。
优选使用二甲基亚砜、四氢呋喃、二甲基甲酰胺或二氯甲烷。
在一个优选的实施方案中,如果式(I-a)的烯醇式盐通过加入强脱质子剂(例如,氢化钠或叔丁醇钾)进行制备,则可免除另外添加酸结合剂。
如果使用酸结合剂,则其为常规的无机碱或有机碱,例如氢氧化钠、碳酸钠、碳酸钾、三乙胺或吡啶。
该反应可在大气压力或提高的压力下进行,并且优选在大气压力下进行。通过常规方法进行后处理。
本发明的活性化合物——具有良好的植物耐受性和对温血动物有利的毒性并具有良好的环境相容性——适于保护植物和植物器官、提高采收产率、改善采收物的质量和用于防治动物有害物,特别是农业、园艺、动物饲养、森林、园林和休闲设施、贮存产品和材料的保护及卫生领域中遇到的昆虫、蛛形纲动物、蠕虫、线虫和软体动物。它们可优选用作作物保护剂。它们对通常敏感和抗性物种及所有或一些发育阶段具有活性。上述害虫包括:
虱目(Anoplura)(Phthiraptera),例如,畜虱属(Damalinia spp.)、血虱属(Haematopinus spp.)、毛虱属(Linognathus spp.)、虱属(Pediculus spp.)、嚼虱属(Trichodectes spp.)。
蛛形纲(Arachnida),例如,粗脚粉螨(Acarus siro)、柑橘瘤瘿螨(Aceria sheldoni)、刺皮瘿螨属(Aculops spp.)、针刺瘿螨属(Aculusspp.)、花蜱属(Amblyomma spp.)、锐缘蜱属(Argas spp.)、牛蜱属(Boophilus spp.)、短须螨属(Brevipalpus spp.)、苜蓿苔螨(Bryobiapraetiosa)、皮螨属(Chorioptes spp.)、鸡皮刺螨(Dermanyssusgallinae)、始叶螨属(Eotetranychus spp.)、梨上瘿螨(Epitrimeruspyri)、真叶螨属(Eutetranychus spp.)、瘿螨属(Eriophyes spp.)、半跗线螨属(Hemitarsonemus spp.)、璃眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、黑寡妇蜘蛛(Latrodectus mactans)、Metatetranychus spp.、小爪螨属(Oligonychus spp.)、钝缘蜱属(Ornithodoros spp.)、全爪螨属(Panonychus spp.)、桔芸锈螨(Phyllocoptruta oleivora)、侧多食跗线螨(Polyphagotar sonemuslatus)、痒螨属(Psoroptes spp.)、扇头蜱属(Rhipicephalus spp.)、根螨属(Rhizoglyphus spp.)、疥螨属(Sarcoptes spp.)、中东金蝎(Scorpio maurus)、Stenotarsonemus spp.、跗线螨属(Tarsonemusspp.)、叶螨属(Tetranychus spp.)、Vasates lycopersici。
Bivalva纲,例如,Dreissena spp.。
唇足目(Chilopoda),例如,地蜈蚣属(Geophilus spp.)、Scutigeraspp.。
鞘翅目(Coleoptera),例如,菜豆象(Acanthoscelides obtectus)、喙丽金龟属(Adoretus spp.)、杨树萤叶甲(Agelastica alni)、叩甲属(Agriotes spp.)、马铃薯鳃角金龟(Amphimallon solstitialis)、家具窃蠹(Anobium punctatum)、星天牛属(Anoplophora spp.)、花象属(Anthonomus spp.)、圆皮蠹属(Anthrenus spp.)、阿鳃金龟属(Apogonia spp.)、Atomaria spp.、毛皮蠹属(Attagenus spp.)、恶条豆象(Bruchidius obtectus)、豆象属(Bruchus spp.)、龟象属(Ceuthorhynchus spp.)、Cleonus mendicus、宽胸叩头虫属(Conoderusspp.)、根颈象属(Cosmopolites spp.)、褐新西兰肋翅鳃角金龟(Costelytra zealandica)、象虫属(Curculio spp.)、杨干隐喙象(Cryptorhynchus lapathi)、皮蠹属(Dermestes spp.)、叶甲属(Diabrotica spp.)、食植瓢虫属(Epilachna spp.)、Faustinus cubae、裸蛛甲(Gibbium psylloides)、黑异爪蔗金龟(Heteronychus arator)、Hylamorpha elegans、北美家天牛(Hylotrupes bajulus)、紫苜蓿叶象(Hypera postica)、Hypothenemus spp.、甘蔗大褐齿爪鳃金龟(Lachnosterna consanguinea)、马铃薯甲虫(Leptinotarsadecemlineata)、稻根象(Lissorhoptrus oryzophilus)、筒喙象属(Lixus spp.)、粉蠹属(Lyctus spp.)、油菜花露尾甲(Meligethesaeneus)、西方五月鳃角金龟(Melolontha melolontha)、Migdolus spp.、墨天牛属(Monochamus spp.)、Naupactus xanthographus、黄蛛甲(Niptus hololeucus)、椰蛀犀金龟(Oryctes rhinoceros)、锯谷盗(Oryzaephilus surinamensis)、黑葡萄耳象(Otiorrhynchussulcatus)、小青花金龟(Oxycetonia jucunda)、辣根猿叶虫(Phaedoncochleariae)、食叶鳃金龟属(Phyllophaga spp.)、日本弧丽金龟(Popillia japonica)、Premnotrypes spp.、油菜金头跳甲(Psylliodeschrysocephala)、蛛甲属(Ptinus spp.)、暗色瓢虫(Rhizobiusventralis)、谷蠹(Rhizopertha dominica)、谷象属(Sitophilus spp.)、尖隐喙象属(Sphenophorus spp.)、茎干象属(Sternechus spp.)、Symphyletes spp.、黄粉虫(Tenebrio molitor)、拟谷盗属(Triboliumspp.)、斑皮蠹属(Trogoderma spp.)、籽象属(Tychius spp.)、脊虎天牛属(Xylotrechus spp.)、距步甲属(Zabrus spp.)。
弹尾目(Collembola),例如,武装棘跳虫(Onychiurus armatus)。
革翅目(Dermaptera),例如,欧洲球螋(Forficula auricularia)。
倍足目(Diplopoda),例如,Blaniulus guttulatus。
双翅目(Diptera),例如,伊蚊属(Aedes spp.)、按蚊属(Anophelesspp.)、花园毛蚊(Bibio hortulanus)、红头丽蝇(Calliphoraerythrocephala)、地中海蜡实蝇(Ceratitis capitata)、金蝇属(Chrysomyia spp.)、锥蝇属(Cochliomyia spp.)、Cordylobiaanthropophaga、库蚊属(Culex spp.)、黄蝇属(Cuterebra spp.)、橄榄大实蝇(Dacus oleae)、人肤蝇(Dermatobia hominis)、果蝇属(Drosophila spp.)、厕蝇属(Fannia spp.)、胃蝇属(Gastrophilusspp.)、黑蝇属(Hylemyia spp.)、Hyppobosca spp.、皮蝇属(Hypodermaspp.)、斑潜蝇属(Liriomyza spp.)、绿蝇属(Lucilia spp.)、家蝇属(Musca spp.)、绿蝽属(Nezara spp.)、狂蝇属(Oestrus spp.)、瑞典麦秆蝇(Oscinella frit)、藜泉蝇(Pegomyia hyoscyami)、草种蝇属(Phorbia spp.)、螫蝇属(Stomoxys spp.)、虻属(Tabanus spp.)、Tannia spp.、欧洲大蚊(Tipula paludosa)、污蝇属(Wohlfahrtiaspp.)。
腹足纲(Gastropoda),例如,Arion spp.、双脐螺属(Biomphalariaspp.)、小泡螺属(Bulinus spp.)、Deroceras spp.、土蜗属(Galbaspp.)、椎实螺属(Lymnaea spp.)、钉螺属(Oncomelania spp.)、琥珀螺属(Succinea spp.)。
蠕虫纲(Helminths),例如,十二指肠钩口线虫(Ancylostomaduodenale)、斯里兰卡钩口线虫(Ancylostoma ceylanicum)、巴西钩口线虫(Acylostoma braziliensis)、钩口线虫属(Ancylostoma spp.)、似引蛔线虫(Ascaris lubricoides)、蛔虫属(Ascari sspp.)、马来布鲁线虫(Brugia malayi)、帝汶布鲁线虫(Brugia timori)、仰口线虫属(Bunostomum spp.)、夏柏特线虫属(Chabertia spp.)、枝睾吸虫属(Clonorchis spp.)、古柏线虫属(Cooperia spp.)、双腔吸虫属(Dicrocoelium spp.)、丝状网尾线虫(Dictyocaulus filaria)、阔节裂头绦虫(Diphyllobothrium latum)、麦地那龙线虫(Dracunculusmedinensis)、细粒棘球绦虫(Echinococcus granulosus)、多房棘球绦虫(Echinococcus multilocularis)、蠕形住肠蛲虫(Enterobiusvermicularis)、Faciola spp.、血毛线虫属(Haemonchus spp.)、异刺线虫属(Heterakis spp.)、矮小啮壳绦虫(Hymenolepis nana)、猪圆线虫属(Hyostrongulus spp.)、罗阿罗阿线虫(Loa Loa)、细颈线虫属(Nema todirus spp.)、结节线虫属(Oesophagostomum spp.)、后睾吸虫属(Opisthorchis spp.)、旋盘尾丝虫(Onchocerca volvulus)、奥斯脱线虫属(Ostertagia spp.)、并殖吸虫属(Paragonimus spp.)、Schistosomen spp.、富氏类圆线虫(Strongyloides fuel leborni)、粪类圆线虫(Strongyloides stercoralis)、粪圆线虫属(Stronyloidesspp.)、牛带绦虫(Taenia saginata)、猪带绦虫(Taenia solium)、旋毛形线虫(Trichinella spiralis)、本地毛形线虫(Trichinellanativa)、株布氏旋毛虫(Trichinella brit ovi)、南方旋毛虫(Trichinella nelsoni)、Trichinella pseudopsiralis、毛圆线虫属(Trichostrongulus spp.)、Trichuris trichuria、班氏吴策线虫(Wuchereria bancrofti)。
此外,也可防治原生动物,例如艾美虫(Eimeria)。
异翅目(Heteroptera),例如,南瓜缘蝽(Anasa tristis)、拟丽蝽属(Antestiopsis spp.)、土长蝽属(Blissus spp.)、俊盲蝽属(Calocoris spp.)、Campylomma livida、异背长蝽属(Caveleriusspp.)、臭虫属(Cimex spp.)、Creontiades dilutus、胡椒缘蝽(Dasynuspiperis)、Dichelops furca tus、厚氏长棒网蝽(Diconocoris hewetti)、棉红蝽属(Dysdercus spp.)、美洲蝽属(Euschistus spp.)、扁盾蝽属(Eurygaster spp.)、Heliopeltis spp.、Horcias nobilellus、稻缘蝽属(Leptocorisa spp.)、叶喙缘蝽(Leptoglossus phyllopus)、草盲蝽属(Lygus spp.)、蔗黑长蝽(Macropes excavatus)、盲蝽科(Miridae)、绿蝽属、Oebalus spp.、Pentomidae、方背皮蝽(Piesmaquadrata)、壁蝽属(Piezodorus spp.)、棉伪斑腿盲蝽(Psallusseriatus)、Pseudacysta persea、红猎蝽属(Rhodnius spp.)、可可褐盲蝽(Sahlbergella singularis)、黑蝽属(Scotinophora spp.)、梨冠网蝽(Stephanitis nashi)、Tibraca spp.、锥猎蝽属(Triatomaspp.)。
同翅目(Homoptera),例如,无网长管蚜属(Acyrthosipon spp.)、Aeneolamia spp.、隆脉木虱属(Agonoscena spp.)、Aleurodes spp.、蔗粉虱属(Aleurolobus barodensis)、Aleurothrixus spp.、杧果叶蝉属(Amrasca spp.)、Anuraphis cardui、肾圆盾蚧属(Aonidiellaspp.)、苏联黄粉蚜(Aphanostigma piri)、蚜属(Aphis spp)、葡萄叶蝉(Arboridia apicalis)、小圆盾蚧属(Aspidiella spp.)、圆盾蚧属(Aspidiotus spp.)、Atanus spp.、茄沟无网蚜(Aulacorthumsolani)、Bemisia spp.、李短尾蚜(Brachycaudus helichrysii)、Brachycolus spp.、甘蓝蚜(Brevicoryne brassicae)、小褐稻虱(Calligypona marginata)、Carneocephala fulgida、甘蔗粉角蚜(Ceratovacuna lanigera)、沫蝉科(Cercopidae)、蜡蚧属(Ceroplastes spp.)、草莓钉蚜(Chaetosiphon fragaefolii)、蔗黄雪盾蚧(Chionaspis tegalensis)、茶绿叶蝉(Chlorita onukii)、核桃黑斑蚜(Chromaphis juglandicola)、黑褐圆盾蚧(Chrysomphalusficus)、玉米叶蝉(Cicadulina mbila)、Coccomytilus halli、软蚧属(Coccus spp.)、茶藨隐瘤蚜(Cryptomyzus ribis)、Dalbulus spp.、Dialeurodes spp.、Diaphorina spp.、白背盾蚧属(Diaspis spp.)、Doralis spp.、履绵蚧属(Drosicha spp.)、西圆尾蚜属(Dysaphisspp.)、灰粉蚧属(Dysmicoccus spp.)、小绿叶蝉属(Empoasca spp.)、绵蚜属(Eriosoma spp.)、Erythroneura spp.、Euscelis bilobatus、咖啡地粉蚧(Geococcus coffeae)、假桃病毒叶蝉(Homalodiscacoagulata)、梅大尾蚜(Hyalopterus arundinis)、吹绵蚧属(Iceryaspp.)、片角叶蝉属(Idiocerus spp.)、扁喙叶蝉属(Idioscopus spp.)、灰飞虱(Laodelphax striatellus)、Lecanium spp.、蛎盾蚧属(Lepidosaphes spp.)、萝卜蚜(Lipaphis erysimi)、长管蚜属(Macrosiphum spp.)、Mahanarva fimbriolata、高粱蚜(Melanaphissacchari)、Metcalfiella spp.、麦无网蚜(Metopolophium dirhodum)、黑缘平翅斑蚜(Monellia costalis)、Monelliopsis pecanis、瘤蚜属(Myzus spp.)、莴苣衲长管蚜(Nasonovia ribisnigri)、黑尾叶蝉属(Nephotettix spp.)、褐飞虱(Nilaparvata lugens)、Oncometopiaspp.、Orthezia praelonga、杨梅缘粉虱(Parabemisia myricae)、Paratrioza spp.、片盾蚧属(Parlatoria spp.)、瘿绵蚜属(Pemphigusspp.)、玉米蜡蝉(Peregrinus maidis)、绵粉蚧属(Phenacoccus spp.)、杨平翅绵蚜(Phloeomyzus passerinii)、忽布疣蚜(Phorodon humuli)、Phylloxera spp.、苏铁褐点并盾蚧(Pinnaspis aspidistrae)、臀纹粉蚧属(Planococcus spp.)、梨形原绵蚧(Protopulvinariapyriformis)、桑白盾蚧(Pseudaulacaspis pentagona)、粉蚧属(Pseudococcus spp.)、木虱属(Psylla spp.)、金小蜂属(Pteromalusspp.)、Pyrilla spp.、笠圆盾蚧属(Quadraspidiotus spp.)、Quesadagigas、平刺粉蚧属(Rastrococcus spp.)、缢管蚜属(Rhopalosiphumspp.)、黑盔蚧属(Saissetia spp.)、Scaphoides titanus、麦二叉蚜(Schizaphis graminum)、苏铁刺圆盾蚧(Selenaspidus articulatus)、长唇基飞虱属(Sogata spp.)、白背飞虱(Sogatella furcifera)、Sogatodess pp.、Stictocepha lafestina、Tenalaphara malayensis、Tinocallis caryaefoliae、广胸沫蝉属(Tomaspis spp.)、声蚜属(Toxoptera spp.)、温室粉虱(Trialeurodes vaporariorum)、个木虱属(Trioza spp.)、小叶蝉属(Typhlocyba spp.)、尖盾蚧属(Unaspisspp.)、Viteus vitifolii。
膜翅目(Hymenoptera),例如,松叶蜂属(Diprion spp.)、实叶蜂属(Hoplocampa spp.)、毛蚁属(Lasius spp.)、小家蚁(Monomoriumpharaonis)、胡蜂属(Vespa spp.)。
等足目(Isopoda),例如,鼠妇(Armadillidium vulgare)、栉水虱(Oniscus asellus)、球鼠妇(Porcellio scaber)。
等翅目(Isoptera),例如,散白蚁属(Reticulitermes spp.)、土白蚁属(Odontotermes spp.)。
鳞翅目(Lepidoptera),例如,桑剑纹夜蛾(Acronicta major)、烦夜蛾(Aedia leucomelas)、地老虎属(Agrotis spp.)、棉叶波纹夜蛾(Alabama argillacea)、干煞夜蛾属(Anticarsia spp.)、Barathrabrassicae、棉潜蛾(Bucculatrix thurberiella)、松尺蠖(Bupaluspiniarius)、亚麻黄卷蛾(Cacoecia podana)、Capua reticulana、苹果小卷蛾(Carpocapsa pomonella)、冬尺蛾(Cheimatobia brumata)、禾草螟属(Chilo spp.)、枞色卷蛾(Choristoneura fumiferana)、葡萄果蠹蛾(Clysia ambiguella)、Cnaphalocerus spp.、埃及金刚钻(Earias insulana)、地中海粉斑螟(Ephestia kuehniella)、黄毒蛾(Euproctis chrysorrhoea)、切根虫属(Euxoa spp.)、脏切夜蛾属(Feltia spp.)、大蜡螟(Galleria mellonella)、Helicoverpa spp.、实夜蛾属(Heliothis spp.)、褐织蛾(Hofmannophilapseudospretella)、茶长卷蛾(Homona magnanima)、苹果巢蛾(Hyponomeuta padella)、贪夜蛾属(Laphygma spp.)、苹细蛾(Lithocolletis blancardella)、绿果冬夜蛾(Lithophaneantennata)、豆白隆切根虫(Loxagrotis albicosta)、毒蛾属(Lymantria spp.)、黄褐天幕毛虫(Malacosoma neustria)、甘蓝夜蛾(Mamestra brassicae)、稻毛胫夜蛾(Mocis repanda)、粘虫(Mythimmaseparata)、Oriaspp.、水稻负泥虫(Oulema oryzae)、小眼夜蛾(Panolisflammea)、红铃麦蛾(Pectinophora gossypiella)、桔潜蛾(Phyllocnistis citrella)、菜粉蝶属(Pieris spp.)、菜蛾(Plutellaxylostella)、斜纹夜蛾属(Prodenia spp.)、Pseudaletia spp.、大豆夜蛾(Pseudoplusia includens)、玉米螟(Pyrausta nubilalis)、灰翅夜蛾属(Spodoptera spp.)、Thermesia gemmatalis、袋谷蛾(Tineapellionella)、幕谷蛾(Tineola bisselliella)、栎绿卷蛾(Tortrixviridana)、粉夜蛾属(Trichoplusia spp.)。
直翅目(Orthoptera),例如,家蟋(Acheta domesticus)、东方蜚蠊(Blatta orientalis)、德国蠊(Blattella germanica)、蝼蛄属(Gryllotalpa spp.)、马德拉蜚蠊(Leucophaea maderae)、飞蝗属(Locusta spp.)、黑蝗属(Melanoplus spp.)、美洲大蠊(Periplanetaamericana)、沙漠蝗(Schistocerca gregaria)。
蚤目(Siphonaptera),例如,角叶蚤属(Ceratophyllus spp.)、印鼠客蚤(Xenopsylla cheopis)。
综合目(Symphyla),例如,Scutigerella immaculata。
缨翅目(Thysanoptera),例如,稻蓟马(Baliothrips biformis)、Enneothrips flavens、花蓟马属(Frankliniella spp.)、网蓟马属(Heliothrips spp.)、温室条篱蓟马(Hercinothrips femoralis)、卡蓟马属(Kakothrips spp.)、葡萄蓟马(Rhipiphorothripscruentatus)、硬蓟马属(Scirtothrips spp.)、Taeniothripscardamoni、蓟马属(Thrips spp.)。
缨尾目(Thysanura),例如,衣鱼(Lepisma saccharina)。
植物寄生线虫包括,例如,鳗线虫属(Anguina spp.)、滑刃线虫属(Aphelenchoides spp.)、刺线虫属(Belonoaimus spp.)、伞滑刃线虫属(Bursaphelenchus spp.)、起绒草茎线虫(Ditylenchusdipsaci)、球异皮线虫属(Globodera spp.)、螺旋线虫属(Heliocotylenchus spp.)、异皮线虫属(Heterodera spp.)、长针线虫属(Longidorus spp.)、根结线虫属(Meloidogyne spp.)、短体线虫属(Pratylenchus spp.)、相似穿孔线虫(Radopholus similis)、小盘旋线虫属(Rotylenchus spp.)、毛刺线虫属(Trichodorus spp.)、矮化线虫属(Tylenchorhynchus spp.)、小垫刃线虫属(Tylenchulusspp.)、半穿刺线虫(Tylenchulus semipenetrans)、剑线虫属(Xiphinema spp.)。
如果合适,本发明化合物也可以一定浓度或施用率用作除草剂、安全剂、生长调节剂或改善植物特性的药剂,或用作杀微生物剂,例如杀真菌剂、抗霉菌剂、杀细菌剂、杀病毒剂(包括抵抗无壳病毒的药剂)或用作抵抗MLO(类支原体)和RLO(类立克次氏体)的药剂。如果合适,它们也可被用作合成其它它活性化合物的中间体或前体。
所有的植物及植物部位均可依据本发明进行处理。本发明中植物的含义应理解为所有的植物及植物种群,例如需要的及不需要的野生植物或作物植物(包括天然存在的作物植物)。作物植物可为可通过常规植物育种和优选法或通过生物技术和遗传工程方法或通过前述方法的结合而获得的植物,包括转基因植物和包括受植物种苗权保护或不受其保护的植物品种。植物部位的含义应理解为植物所有的地上及地下部位及植物器官,例如芽、叶、花和根,可提及的实例有叶、针叶、茎、干、花、子实体、果实、种子、根、块茎和根茎。植物部位还包括采收物,及无性与有性繁殖物,例如插枝、块茎、根茎、分枝和种子。
根据本发明用活性化合物对植物及植物部位进行的处理,通过常规处理方法直接进行或使化合物作用于其环境、生境或贮存空间而进行,所述常规处理方法例如浸液、喷雾、蒸发、弥雾、撒播、涂抹、注射,并且,对于繁殖物,特别是对于种子,还可施用一层或多层包衣。
本发明活性化合物可转化为常规制剂,例如溶液剂、乳剂、可湿性粉剂、水基和油基悬浮剂、粉剂、粉末剂、膏剂、可溶性粉剂、可溶性颗粒剂、撒播颗粒剂、悬乳浓缩乳剂、经活性化合物浸渍的天然材料、经活性化合物浸渍的合成材料、肥料,以及聚合物中的微胶囊剂。
这些制剂以已知方式制备,例如将活性化合物与填充剂混合,即,与液体溶剂和/或固体载体混合,任选使用表面活性剂,即乳化剂和/或分散剂和/或发泡剂。这些制剂在适合的工厂中进行或在施用之前或使用过程中进行。
适宜用作助剂的为适于将特定特性赋予组合物本身和/或由其制得的制剂(例如喷洒液剂、种子包衣剂)的物质,所述特性例如某些技术特性和/或特定的生物特性。适合的助剂通常为:填充剂、溶剂和载体。
适宜的填充剂为,例如水、极性和非极性有机化学液体,例如芳香烃和非芳香烃类(例如石蜡、烷基苯、烷基萘、氯苯)、醇和多元醇(如果合适,其还可被取代、醚化和/或酯化)、酮(例如丙酮、环己酮)、酯(包括脂肪和油)以及(聚)醚,未被取代的和被取代的胺、酰胺、内酰胺(例如N-烷基吡咯烷酮)以及内酯、砜和亚砜(例如二甲基亚砜)。
如果所用填充剂为水,还可使用例如有机溶剂作为助溶剂。适宜的液体溶剂主要有:芳香族化合物,例如或二甲苯、甲苯或烷基萘;氯代芳香族化合物和氯代脂肪族烃,例如氯苯、氯乙烯或二氯甲烷;脂肪族烃,例如环己烷或石蜡,如石油馏分、矿物油和植物油;醇,例如丁醇或乙二醇,及其醚和酯;酮,例如丙酮、甲乙酮、甲基异丁基酮或环己酮;强极性溶剂,例如二甲基亚砜;以及水。
适宜的固体载体有:
例如铵盐,和粉碎的天然矿物如高岭土、粘土、滑石、白垩、石英、凹凸棒石、蒙脱石或硅藻土,及粉碎的合成矿如细分散的二氧化硅、氧化铝和硅酸盐;适用于颗粒剂的固体载体有:例如粉碎并分级的天然岩石,例如方解石、大理石、浮石、海泡石和白云石;和合成的无机及有机粉颗粒;及有机物颗粒,例如纸、木屑、椰壳、玉米穗轴和烟草茎;适宜的乳化剂和/或发泡剂有:例如非离子及阴离子乳化剂,例如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,如烷基芳基聚乙二醇醚,烷基磺酸盐、烷基硫酸盐、芳基磺酸盐,以及蛋白质水解产物;适宜的分散剂有:非离子物质和/或离子物质,例如醇-POE和/或醇-POP醚、酸和/或POP-POE酯、烷基芳基和/或POP-POE醚、脂肪-和/或POP-POE加合物、POE-和/或POP-多元醇衍生物、POE-和/或POP-脱水山梨糖醇加合物或蔗糖加合物、烷基或芳基硫酸酯、烷基或芳基磺酸酯,及烷基或芳基磷酸酯,或者相应的PO-醚加合物。此外适宜的低聚物或聚合物,例如由乙烯单体、丙烯酸、由EO和/或PO单独地或与例如(聚)醇或(聚)胺相结合而得到的低聚物或聚合物。也可使用木质素及其磺酸衍生物、未经改性的和经改性的纤维素、芳香族和/或脂肪族磺酸以及它们与甲醛的加合物。
制剂中可使用增粘剂,例如羧甲基纤维素,和粉末、颗粒或胶乳形式的天然及合成聚合物,例如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯;及天然磷脂,例如脑磷脂和卵磷脂,及合成磷脂。
可使用着色剂,例如无机颜料,如氧化铁、氧化钛和普鲁士蓝;及有机染料,例如茜素染料、偶氮染料和金属酞菁染料;及微量营养物质,例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
其它可使用的添加剂有香料、任选经改性的矿物油或植物油、蜡和营养物质(包括微量营养物质),例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
还可存在的有稳定剂,例如低温稳定剂、防腐剂、抗氧化剂、光稳定剂或其它用于改进化学和/或物理稳定性的试剂。
制剂通常含有0.01和98重量%之间的活性化合物,优选0.5和90%之间。
本发明活性化合物可以其市售制剂或者以将所述制剂与其它活性化合物混合所制备的使用形式而使用,所述其它活性化合物例如杀昆虫剂、引诱剂、消毒剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂、除草剂、安全剂、肥料或化学信息素。
特别有利的混合组分为例如以下化合物:
杀真菌剂:
核酸合成抑制剂
苯霜灵(benalaxyl)、精苯霜灵(benalaxyl-M)、乙嘧酚磺酸酯(bupirimate)、chiralaxyl、clozylacon、二甲嘧酚(dimethirimol)、乙嘧酚(ethirimol)、呋霜灵(furalaxyl)、恶霉灵(hymexazole)、甲霜灵(metalaxyl)、高效霜灵(metalaxyl-M)、呋酰胺(ofurace)、噁霜灵(oxadixyl)、喹菌酮(oxolinic acid)
有丝分裂和细胞分裂抑制剂
苯菌灵(benomyl)、多菌灵(carbendazim)、乙霉威(diethofencarb)、麦穗宁(fuberidazole)、戊菌隆(pencycuron)、噻菌灵(thiabendazole)、甲基硫菌灵(thiophanate-methyl)、苯酰菌胺(zoxamide)
呼吸链复合物I的抑制剂
氟嘧菌胺(diflumetorim)
呼吸链复合物II的抑制剂
啶酰菌胺(boscalid)、萎锈灵(carboxin)、甲呋酰胺(fenfuram)、氟酰胺(flutolanil)、呋吡菌胺(furametpyr)、灭锈胺(mepronil)、氧化萎锈灵(oxycarboxin)、吡噻菌胺(penthiopyrad)、溴氟唑菌(thifluzamide)
呼吸链复合物III的抑制剂
嘧菌酯(azoxystrobin)、氰霜唑(cyazofamid)、醚菌胺(dimoxystrobin)、enestrobin、噁唑菌酮(famoxadone)、咪唑菌酮(fenamidone)、氟嘧菌酯(fluoxastrobin)、醚菌酯(kresoxim-methyl)、苯氧菌胺(metominostrobin)、肟醚菌胺(orysastrobin)、唑菌胺酯(pyraclostrobin)、啶氧菌酯(picoxystrobin)、肟菌酯(trifloxystrobin)
解偶剂
敌螨普(dinocap)、氟啶胺(fluazinam)
ATP产生抑制剂
三苯基乙酸锡(fentin acetate)、三苯基氯化锡(fentin chloride)、毒菌锡(fentin hydroxide)、硅噻菌胺(silthiofam)
氨基酸生物合成和蛋白质生物合成抑制剂
胺扑灭(andoprim)、灭瘟素(blasticidin-S)、嘧菌环胺(cyprodinil)、春雷霉素(kasugamycin)、春雷霉素一水合盐酸盐(kasugamycin hydrochloride hydrate)、嘧菌胺(mepanipyrim)、嘧霉胺(pyrimethanil)
信号转导抑制剂
拌种咯(fenpiclonil)、咯菌腈(fludioxonil)、苯氧喹啉(quinoxyfen)
脂类和膜合成抑制剂
乙菌利(chlozolinate)、异菌脲(iprodione)、腐霉利(procymidone)、乙烯菌核利(vinclozolin)
氨丙膦酸(ampropylfos)、potassium-ampropylfos、敌瘟磷(edifenphos)、异稻瘟净(iprobenfos)(IBP)、稻瘟灵(isoprothiolane)、吡菌磷(pyrazophos)
甲基立枯磷(tolclofos-methyl)、联苯
iodocarb、霜霉威(propamocarb)、霜霉威盐酸盐(propamocarbhydrochloride)
麦角固醇生物合成抑制剂
环酰菌胺(fenhexamid),
氧环唑(azaconazole)、双苯三唑醇(bitertanol)、糠菌唑(bromuconazole)、环唑醇(cyproconazole)、苄氯三唑醇(diclobutrazole)、苯醚甲环唑(difenoconazole)、烯唑醇(diniconazole)、达克利(diniconazole-M)、氟环唑(epoxiconazole)、乙环唑(etaconazole)、腈苯唑(fenbuconazole)、氟喹唑(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、呋菌唑(furconazole)、呋醚唑(furconazole-cis)、己唑醇(hexaconazole)、亚胺唑(imibenconazole)、种菌唑(ipconazole)、叶菌唑(metconazole)、腈菌唑(myclobutanil)、多效唑(paclobutrazol)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙硫菌唑(prothioconazole)、硅氟唑(simeconazole)、戊唑醇(tebuconazole)、四氟醚唑(tetraconazole)、三唑酮(triadimefon)、唑菌醇(triadimenol)、灭菌唑(triticonazole)、烯效唑(uniconazole)、伏立康唑(voriconazole)、抑霉唑(imazalil)、烯菌灵(imazalil sulphate)、恶咪唑(oxpoconazole)、氯苯嘧啶醇(fenarimol)、呋嘧醇(flurprimidole)、氟苯嘧啶醇(nuarimol)、啶斑肟(pyrifenox)、嗪氨灵(triforine)、稻瘟酯(pefurazoate)、咪鲜胺(prochloraz)、氟菌唑(triflumizole)、烯霜苄唑(viniconazole)
aldimorph、十二环吗啉(dodemorph)、十二环吗啉乙酸盐(dodemorph acetate)、丁苯吗啉(fenpropimorph)、十三吗啉(tridemorph)、苯锈啶(fenpropidin)、螺环菌胺(spiroxamine),
萘替芬(naftifine)、稗草丹(pyributicarb)、特比萘芬(terbinafine)
细胞壁合成抑制剂
苯噻菌胺(benthiavalicarb)、双丙氨膦(bialaphos)、烯酰吗啉(dimethomorph)、氟吗啉(flumorph)、异丙菌胺(iprovalicarb)、多抗霉素(polyoxins)、多氧霉素(polyoxorim)、有效霉素A(validamycin A)
黑色素生物合成抑制剂
环丙酰菌胺(capropamid)、双氯氰菌胺(diclocymet)、氰菌胺(fenoxanil)、四氯苯酞(phthalid)、咯喹酮(pyroquilon)、三环唑(tricyclazole)
抗性诱导剂
苯并噻二唑(acibenzolar-S-methyl)、烯丙苯噻唑(probenazole)、噻酰菌胺(tiadinil)
多位点化合物
敌菌丹(captafol)、克菌丹、百菌清(chlorothalonil)、铜盐例如:氢氧化铜、环烷酸铜、氯氧化铜(copper oxychloride)、硫酸铜、一氧化铜、喹啉铜(oxine-copper)和波尔多液、苯氟磺胺(dichlofluanid)、二氰蒽醌(dithianon)、多果定(dodine)、多果定游离碱(dodine free base)、福美铁(ferbam)、灭菌丹(folpet)、氟灭菌丹(fluorofolpet)、双胍辛盐(guazatine)、双胍辛乙酸盐(guazatine acetate)、双胍辛胺(iminoctadine)、双胍辛烷基苯磺酸盐(iminoctadine albesilate)、双胍辛胺乙酸盐(iminoctadinetriacetate)、代森锰铜(mancopper)、代森锰锌(mancozeb)、代森锰(maneb)、代森联(metiram)、代森联锌(metiram zinc)、丙森锌(propineb)、硫和硫制剂包括多硫化钙、福美双(thiram)、甲苯氟磺胺(tolylfluanid)、代森锌(zineb)、福美锌(ziram)
未知机理化合物
amibromdol、苯噻硫氰(benthiazole)、bethoxazin、卡巴西霉素(capsimycin)、香芹酮(carvone)、灭螨猛(chinomethionat)、氯化苦(chloropicrin)、硫杂灵(cufraneb)、环氟菌胺(cyflufenamid)、霜脲氰(cymoxanil)、棉隆(dazomet)、咪菌威(debacarb)、哒菌酮(diclomezine)、双氯酚(dichlorophen)、氯硝胺(dicloran)、野燕枯(difenzoquat)、野燕枯甲基硫酸酯(difenzoquat methyl sulphate)、二苯胺(diphenylamine)、韩乐宁(ethaboxam)、嘧菌腙(ferimzone)、氟酰菌胺(flumetover)、磺菌胺(flusulfamide)、氟啶酰菌胺(fluopicolide)、氟氯菌核利(fluoroimide)、六氯苯(hexachlorobenzene)、8-羟基喹啉硫酸盐、人间霉素(irumamycin)、磺菌威(methasulphocarb)、苯菌酮(metrafenone)、异硫氰酸甲酯(methyl isothiocyanate)、米多霉素(mildiomycin)、多马霉素(natamycin)、福美镍(nickel dimethyl dithiocarbamate)、酞菌酯(nitrothal-isopropyl)、辛噻酮(octhilinone)、oxamocarb、oxyfenthiin、五氯苯酚(pentachlorophenol)及其盐、2-苯基苯酚及其盐、病花灵(piperalin)、propanosine-sodium、丙氧喹啉(proquinazid)、硝吡咯菌素(pyrrolnitrin)、五氯硝基苯(quintozene)、叶枯酞(tecloftalam)、四氯硝基苯(tecnazene)、咪唑嗪(triazoxide)、水杨菌胺(trichlamide)、氰菌胺(zarilamid)及2,3,5,6-四氯-4-(甲基磺酰基)吡啶、N-(4-氯-2-硝基苯基)-N-乙基-4-甲基苯磺酰胺、2-氨基-4-甲基-N-苯基-5-噻唑甲酰胺、2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺、3-[5-(4-氯苯基)-2,3-二甲基异噁唑烷-3-基]吡啶、顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)环庚醇、2,4-二氢-5-甲氧基-2-甲基-4-[[[[1-[3-(三氟甲基)苯基]亚乙基]氨基]氧基]甲基]苯基]-3H-1,2,3-三唑-3-酮(185336-79-2)、1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯、3,4,5-三氯-2,6-吡啶二腈、2-[[[环丙基[(4-甲氧基苯基)亚氨基]甲基]硫基]甲基]-α-(甲氧基亚甲基)苯乙酸甲酯、4-氯-α-丙炔氧基-N-[2-[3-甲氧基-4-(2-丙炔氧基)苯基]乙基]苯乙酰胺、(2S)-N-[2-[4-[[3-(4-氯苯基)-2-丙炔基]氧]-3-甲氧基苯基]乙基]-3-甲基-2-[(甲基磺酰基)氨基]丁酰胺、5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)[1,2,4]三唑并[1,5-a]嘧啶、5-氯-6-(2,4,6-三氟苯基)-N-[(1R)-1,2,2-三甲基丙基][1,2,4]三唑并[1,5-a]嘧啶-7-胺、5-氯-N-[(1R)-1,2-二甲基丙基]-6-(2,4,6-三氟苯基)[1,2,4]三唑并[1,5-a]嘧啶-7-胺、N-[1-(5-溴-3-氯吡啶-2-基)乙基]-2,4-二氯烟酰胺、N-(5-溴-3-氯吡啶-2-基)甲基-2,4-二氯烟酰胺、2-丁氧基-6-碘-3-丙基苯并吡喃-4-酮、N-{(Z)-[(环丙基甲氧基)亚氨基][6-(二氟甲氧基)-2,3-二氟苯基]甲基}-2-苯乙酰胺、N-(3-乙基-3,5,5-三甲基环己基)-3-甲酰基氨基-2-羟基苯甲酰胺、2-[[[[1-[3-(1-氟-2-苯基乙基)氧基]苯基]亚乙基]氨基]氧基]甲基]-α-(甲氧基亚氨基)-N-甲基-αE-苯乙酰胺、N-{2-[3-氯-5-(三氟甲基)吡啶-2-基]乙基}-2-(三氟甲基)苯甲酰胺、N-(3',4'-二氯-5-氟联苯基-2-基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、N-(6-甲氧基-3-吡啶基)环丙烷甲酰胺、1-[(4-甲氧基苯氧基)甲基]-2,2-二甲基丙基-1H-咪唑-1-羧酸、O-[1-[(4-甲氧基苯氧基)甲基]-2,2-二甲基丙基]-1H-咪唑-1-硫代羟酸、2-(2-{[6-(3-氯-2-甲基苯氧基)-5-氟嘧啶-4-基]氧基}苯基)-2-(甲氧基亚氨基)-N-甲基乙酰胺
杀细菌剂:
溴硝丙二醇(bronopol)、双氯酚、三氯甲基吡啶(nitrapyrin)、福镁镍(nickel dimethyldithiocarbamate)、春雷霉素、辛噻酮(octhilinone)、羧酸呋喃(furancarboxylic acid)、土霉素(oxytetracycline)、噻菌灵、链霉素(streptomycin)、叶枯酞、硫酸铜及其它铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
乙酰胆碱酯酶(AChE)抑制剂
氨基甲酸酯类
例如,棉铃威(alanycarb)、涕灭威(aldicarb)、涕灭砜威(aldoxycarb)、除害威(allyxycarb)、灭害威(aminocarb)、噁虫威(bendiocarb)、丙硫克百威(benfuracarb)、必克虱(bufencarb)、畜虫威(butacarb)、丁酮威(butocarboxim)、丁酮砜威(butoxycarboxim)、甲萘威(carbaryl)、克百威(carbofuran)、丁硫克百威(carbosulphan)、除线威(cloethocarb)、敌蝇威(dimetilan)、乙硫苯威(ethiofencarb)、丁苯威(fenobucarb)、苯硫威(fenothiocarb)、伐虫脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、威百亩(metam-sodium)、甲硫威(methiocarb)、灭多威(methomyl)、速灭威(metolcarb)、杀线威(oxamyl)、抗蚜威(pirimicarb)、猛杀威(promecarb)、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)
有机磷酸酯类
例如,乙酰甲胺磷(acephate)、甲基吡恶磷(azamethiphos)、谷硫磷(azinphos-methyl)、乙基谷硫磷(azinphos-ethyl)、乙基溴硫磷(bromophos-ethyl)、溴苯烯磷(bromfenvinfos(-methyl))、特嘧硫磷(butathiofos)、硫线磷(cadusafos)、三硫磷(carbophenothion)、氯氧磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲硫磷(chlormephos)、甲基毒死蜱(chlorpyrifos-methyl)、乙基毒死蜱、蝇毒磷(coumaphos)、苯腈磷(cyanofenphos)、杀螟腈(cyanophos)、毒虫畏(chlorfenvinphos)、甲基内吸磷(demeton-S-methyl)、砜吸磷(demeton-S-methylsulphone)、氯亚胺硫磷(dialifos)、二嗪农(diazinon)、除线磷(dichlofenthion)、敌敌畏(dichlorvos/DDVP)、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、蔬果磷(dioxabenzofos)、乙拌磷(disulfoton)、苯硫磷(EPN)、乙硫磷(ethion)、灭线磷(ethoprophos)、乙嘧硫磷(etrimfos)、伐灭磷(famphur)、苯线磷(fenamiphos)、杀螟硫磷(fenitrothion)、丰索磷(fensulfothion)、倍硫磷(fenthion)、吡氟硫磷(flupyrazofos)、地虫硫磷(fonofos)、安硫磷(formothion)、丁苯硫磷(fosmethilan)、噻唑磷(fosthiazate)、庚烯磷(heptenophos)、碘硫磷(iodofenphos)、异稻瘟净(iprobenfos)、氯唑磷(isazofos)、异柳磷(isofenphos)、O-水杨酸异丙酯、噁唑啉(isoxathion)、马拉硫磷(malathion)、灭蚜磷(mecarbam)、虫螨畏(methacrifos)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧化乐果(omethoate)、亚砜磷(oxydemeton-methyl)、甲基对硫磷(parathion methyl)、对硫磷(parathion-ethyl)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀硫磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、乙丙磷威(phosphocarb)、腈肟磷(phoxim)、虫螨磷(pirimiphos-methyl)、乙基虫螨磷(pirimiphos-ethyl)、丙溴磷(profenofos)、丙虫磷(propaphos)、胺丙畏(propetamphos)、丙硫磷(prothiofos)、发硫磷(prothoate)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、pyridathion、喹硫磷(quinalphos)、硫线磷(sebufos)、治螟磷(sulfotep)、硫丙磷(sulprofos)、丁基嘧啶磷(tebupirimfos)、双硫磷(temephos)、特丁硫磷(terbufos)、杀虫畏(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(triclorfon)、蚜灭磷(vamidothion)
钠通道调节剂/电压依赖性(voltage-dependent)钠通道阻断剂
拟除虫菊酯类
例如,氟丙菊酯(acrinathrin)、烯丙菊酯(d-顺-反,d-反)(allethrin(d-cis-trans,d-trans))、高效氟氯氰菊酯(beta-cyfluthrin)、联苯菊酯(bifenthrin)、生物烯丙菊酯(bioallethrin)、生物烯丙菊酯-S-环戊基异构体、bioethanomethrin、生物氯菊酯(biopermethrin)、生物苄呋菊酯(bioresmethrin)、chlovaporthrin、顺-氯氰菊酯、顺-苄呋菊酯(cis-resmethrin)、顺-氯菊酯(cis-permethrin)、功夫菊酯(clocythrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、氯氟氰菊酯(cyhalothrin)、氯氰菊酯(α-、β-、θ-、ζ-)(cypermethrin(alpha-,beta-,theta-,zeta-))、苯醚氰菊酯(cyphenothrin)、溴氰菊酯(deltamethrin)、右旋烯炔菊酯(1R异构体)(empenthrin(1Risomer))、S-氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、五氟苯菊酯(fenfluthrin)、甲氰菊酯(fenpropathrin)、吡氯氰菊酯(fenpyrithrin)、氰戊菊酯(fenvalerate)、溴氟菊酯(flubrocythrinate)、氟氰戊菊酯(flucythrinate)、三氟醚菊酯(flufenprox)、氟氯苯菊酯(flumethrin)、氟胺氰菊酯(fluvalinate)、fubfenprox、γ-氯氟氰菊酯(gamma-cyhalothrin)、咪炔菊酯(imiprothrin)、噻嗯菊酯(kadethrin)、高效氯氟氰菊酯(lambda-cyhalothrin)、甲氧苄氟菊酯(metofluthrin)、氯菊酯(顺-、反-)、苯醚菊酯(1R-反式异构体)(phenothrin(1R-trans isomer)、右旋炔丙菊酯(prallethrin)、丙氟菊酯(profluthrin)、protrifenbute、反灭虫菊(pyresmethrin)、苄呋菊酯、噻嗯菊酯(RU-15525)、氟硅菊酯(silafluofen)、氟胺氰菊酯(tau-fluvalinate)、七氟菊酯(tefluthrin)、环戊烯丙菊酯(terallethrin)、胺菊酯(1R异构体)(tetramethrin(1Risomer))、四溴菊酯(tralomethrin)、四氟苯菊酯(transfluthrin)、溴氟菊酯(ZXI8901)、除虫菊素(pyrethrins)(除虫菊(pyrethrum))
DDT
噁二嗪类(oxadiazines)
例如噁二唑虫(indoxacarb)
缩氨基脲类,
例如metaflumizone(BAS3201)
乙酰胆碱受体激动剂/拮抗剂
氯烟碱基类(chloronicotinyls),
例如,吡虫清(acetamiprid)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、烯啶虫胺(nitenpyram)、硝虫噻嗪(nithiazine)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)
烟碱(nicotine)、杀虫磺(bensultap)、巴丹(cartap)
乙酰胆碱受体调节剂
多杀霉素类(spinosyn),
例如多杀菌素(spinosad)
GABA门控性氯通道拮抗剂
有机氯类,
例如,毒杀芬(camphechlor)、氯丹(chlordane)、硫丹(endosulphan)、林丹(gamma-HCH)、六六六(HCH)、七氯(heptachlor)、林丹(lindane)、甲氧滴滴涕(methoxychlor)
fiprole类,
例如,乙酞虫腈(acetoprole)、乙虫腈(ethiprole)、氟虫腈(fipronil)、pyrafluprole、pyriprole、氟吡唑虫(vaniliprole)
氯通道激活剂类
Mectin类,
例如,阿维菌素(abamectin)、埃玛菌素(emamectin)、埃玛菌素苯甲酸盐(emamectin-benzoate)、齐墩螨素(ivermectin)、lepimectin、米尔倍霉素(milbemycin)
保幼激素模拟物(mimetic)类,
例如,苯虫醚(diofenolan)、保幼醚(epofenonane)、苯氧威(fenoxycarb)、烯虫乙酯(hydroprene)、烯虫炔酯(kinoprene)、烯虫酯(methoprene)、吡丙醚(pyriproxifen)、烯虫硫酯(triprene)
蜕皮激素激动剂/干扰剂类,
二酰基肼类,
例如,环虫酰肼(chromafenozide)、氯虫酰肼(halofenozide)、甲氧虫酰肼(methoxyfenozide)、虫酰肼(tebufenozide)
几丁质生物合成抑制剂类
苯甲酰脲类,
例如,双三氟虫脲(bistrifluron)、氟啶脲(chlofluazuron)、除虫脲(diflubenzuron)、啶蜱脲(fluazuron)、氟环脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、虱螨脲(lufenuron)、氟酰脲(novaluron)、多氟脲(noviflumuron)、氟幼脲(penfluron)、氟苯脲(teflubenzuron)、杀铃脲(triflumuron)
噻嗪酮(buprofezin)
灭蝇胺(cyromazine)
氧化磷酸化抑制剂类,ATP干扰剂类
丁醚脲(diafenthiuron)
有机锡类,
例如三唑锡(azocyclotin)、三环锡(cyhexatin)、苯丁锡(fenbutatin-oxide)
通过间断H-质子梯度而起作用的氧化磷酸化去偶剂类
吡咯类,
例如虫螨腈(chlorfenapyr)
二硝基酚类,
例如乐杀螨(binapacyrl)、消螨通(dinobuton)、敌螨普(dinocap)、二硝甲酚(DNOC)、meptyldinocap
位点-I电子转移抑制剂类
METI类,
例如喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、嘧螨醚(pyrimidifen)、哒螨灵(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)
伏蚁腙(hydramethylnon)
三氯杀螨醇(dicofol)
位点-II电子转移抑制剂类
鱼藤酮(rotenone)
位点-III电子转移抑制剂类
灭螨醌(acequinocyl)、嘧螨酯(fluacrypyrim)
昆虫肠道膜微生物干扰剂类
苏云金杆菌(Bacillus thuringiensis)菌株
脂质合成抑制剂类
特窗酸类,
例如,螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)
特特拉姆酸类(tetramic acids),
例如,spirotetramate、顺-3-(2,5-二甲基苯基)-4-羟基-8-甲氧基-1-氮杂螺[4.5]癸-3-烯-2-酮
甲酰胺类,
例如氟啶虫酰胺(flonicamid)
章鱼胺能激动剂类,
例如虫螨脒(amitraz)
镁刺激的ATP酶抑制剂类,
炔螨特(propargite)
沙蚕毒素类似物,
例如硫赐安(thiocyclam hydrogen oxalate)、杀虫双(thiosultap-sodium)
杀罗定(ryanodine)受体激动剂类,
苯并二甲酰胺类(benzodicarboxamides),
例如flubendiamid
邻氨基苯甲酰胺类,
例如Rynaxypyr(3-溴-N-{4-氯-2-甲基-6-[(甲氨基)羰基]苯基}-1-(3-氯吡啶-2-基)-1H-吡唑-5-甲酰胺)
生物制剂类、激素类或信息素类
艾扎丁(azadirachtin)、杆菌属种(Bacillus spec.)、僵菌属种(Beauveria spec.)、十二碳二烯醇(codlemone)、绿僵菌属种(Metarrhizium spec.)、拟青霉属种(Paecilomyces spec.)、敌贝特(thuringiensin)、轮枝菌属种(Verticillium spec.)
具有未知或未确定作用机理的活性化合物类
熏蒸剂类,
例如,磷化铝、一溴甲烷、磺酰氟
拒食剂类,
例如,冰晶石、氟啶虫酰胺(flonicamid)、吡蚜酮(pymetrozine)
螨生长抑制剂类,
例如,四螨嗪(clofentezine)、乙螨唑(etoxazole)、噻螨酮(hexythiazox)
amidoflumet、benclothiaz、苯螨特(benzoximate)、联苯肼酯(bifenazate)、溴螨酯(bromopropylate)、噻嗪酮(buprofezin)、灭螨锰(chinomethionat)、杀虫脒(chlordimeform)、乙酯杀螨醇(chlorobenzilate)、氯化苦(chloropicrin)、clothiazoben、cycloprene、cyflumetofen、地昔尼尔(dicyclanil)、fenoxacrim、氟硝二苯胺(fentrifanil)、噻唑螨(flubenzimine)、flufenerim、氟螨嗪(flutenzin)、诱虫十六酯(gossyplure)、伏蚁腙(hydramethylnone)、japonilure、恶虫酮(metoxadiazone)、石油、增效醚(piperonyl butoxide)、油酸钾、啶虫丙醚(pyridalyl)、氟虫胺(sulfluramid)、三氯杀螨砜(tetradifon)、杀螨硫醚(tetrasul)、苯螨噻(triarathene)、增效炔醚(verbutin)
还可与其它已知活性化合物例如除草剂、肥料、生长调节剂、安全剂、信息化学素相混合,或者与改善植物特性的试剂相混合。
本发明的活性化合物用作杀虫剂时,还可以其市售制剂的形式和由所述制剂与增效剂混合所制备的使用形式存在。增效剂为提高活性化合物的活性、而其本身不必具有活性的化合物。
本发明的活性化合物用作杀虫剂时,还可以其市售制剂的形式和由所述制剂与抑制剂混合所制备的使用形式存在,所述抑制剂可减少活性化合物用于植物的环境、植物表面部位或植物组织后的降解。
由市售制剂制备的使用形式的活性化合物含量可在较宽的范围内变化。使用形式的活性化合物浓度可为0.00000001-95重量%的活性化合物,优选0.00001和1重量%之间。
所述化合物以适合于使用形式的常规方式施用。
如上所述,可依据本发明处理所有的植物和其部位。在一个优选实施方案中,处理了野生植物种和植物栽培种,或由常规生物育种方法例如杂交或原生质体融合而获得的植物品种和植物栽培种,以及它们的部位。在另一个优选实施方案中,处理了由基因工程方法——如果合适,与常规方法相结合——而获得的转基因植物和植物栽培种(遗传修饰的生物体(genetic modified organism))及其部位。术语“部位”、“植物的部位”和“植物部位”解释如上。
特别优选依据本发明进行处理的植物为各自市售或使用的植物栽培种。植物栽培种的含义理解为由常规育种、诱变或重组DNA技术而获得的具有新特性(“特征”)的植物。它们可以是栽培种、生物型或基因型。
依据植物品种或植物变种、其种植地点和生长条件(土壤、气候、生长期、营养(diet)),本发明的处理也可产生超加和(“协同”)效应。由此可取得如下超过实际预期的效果,例如降低依据本发明使用的物质和组合物的施用量和/或加宽其作用谱和/或提高其活性、改善植物生长状况、提高高温或低温耐受性、提高对干旱或水或土壤含盐量的耐受性、提高开花品质、使采收更简易、加速成熟、提高采收产率、提高采收产品的质量和/或提高其营养价值、改善采收产品的贮存稳定性和/或其加工性能。
优选依据本发明处理的转基因植物或植物栽培种(即通过遗传工程而获得的品种)包括通过基因修饰接受了遗传物质的所有植物,所述遗传物质赋予了所述植物特别有利的有用特性(“特征”)。所述特征的实例有改善植物生长状况、提高高温或低温耐受性、提高对干旱或水或土壤含盐量的耐受性、提高开花品质、使采收更简易、加速成熟、提高采收产率、提高采收产品的质量和/或提高其营养价值、改善采收产品的贮存稳定性和/或其加工性能。特别强调的所述特征的其它实例有改善植物对动物和微生物有害物的抵抗力,例如对昆虫、螨虫、植物致病真菌、细菌和/或病毒的抵抗力,以及提高植物对某些除草活性化合物的耐受性。可提及的转基因植物的实例为重要的作物植物,例如谷物(小麦、稻)、玉米、大豆、马铃薯、甜菜、西红柿、豌豆及其它蔬菜品种、棉花、烟草、油菜和果实植物(果实为苹果、梨、柑橘类的水果及葡萄),特别强调的是玉米、大豆、马铃薯、棉花、烟草和油菜。特别强调的特征为通过在植物体内形成的毒素,特别是由苏云金杆菌的遗传物质(例如基因Cry I A(a)、Cry I A(b)、Cry I A(c)、Cry II A、Cry III A、CryIIIB2、Cry9c、Cry2Ab、Cry3Bb和Cry I F及其结合)在植物体内形成的毒素,来提高植物对昆虫、蛛形纲动物、线虫和蛞蝓以及蜗牛的抵抗力(以下简称为“Bt植物”)。还特别强调的特征为通过系统获得性抗性(SAR)、系统素、植物抗毒素、引发物(elicitor)和抗性基因以及相应的表达蛋白质和毒素来提高植物对真菌、细菌和病毒的抵抗力。此外特别强调的特征为提高植物对某些除草活性化合物的耐受性,例如对咪唑啉酮类、磺酰脲类、草甘磷(glyphosate)或草丁膦(phosphinotricin)的耐受性(例如“PAT”基因)。赋予所述所需特征的基因也可在转基因植物体内相互结合而存在。可提及的“Bt植物”的实例有市售的商品名称为YIELD(例如玉米、棉花、大豆)、(例如玉米)、(例如玉米)、(棉花)、(棉花)和(马铃薯)的玉米品种、棉花品种、大豆品种和马铃薯品种。可提及的除草剂耐受性植物的实例有市售的商品名称为Roundup(具有草甘磷耐受性,例如玉米、棉花、大豆)、Liberty(具有草丁膦耐受性,例如油菜)、(具有咪唑啉酮耐受性)和(具有磺酰脲耐受性,例如玉米)的玉米品种、棉花品种和大豆品种。可提及的具有除草剂抗性的植物(以常规的除草剂耐受性方式育种的植物)包括名称为(例如玉米)的市售品种。当然,以上叙述也适用于具有所述基因特征或待开发基因特征的植物栽培种,所述植物栽培种将在未来进行开发和/或上市。
所列植物可用本发明通式I的化合物和/或本发明活性化合物混合物以特别有利的方式依据本发明进行处理。上述活性化合物或混合物的优选范围也适用于所述植物的处理。特别强调用本说明书中具体提及的化合物或混合物处理植物。
本发明活性化合物不仅对植物害虫、卫生害虫和贮存产品害虫具有活性,而且对兽医领域中的动物寄生虫(体外寄生虫和体内寄生虫)例如硬蜱、软蜱、兽疥螨、叶螨、蝇(叮咬和吸食)、寄生蝇幼虫、虱、毛虱、羽虱和蚤也具有活性。所述寄生虫包括:
虱目(Anoplurida),例如血虱属(Haematopinus spp.)、毛虱属(Linognathus spp.)、虱属(Pediculus spp.)、Phtirus spp.、管虱属(Solenopotes spp.)。
食毛目(Mallophagida)及钝角亚目(Amblycerina)和细角亚目(Ischnocerina),例如毛羽虱属(Trimenopon spp.)、禽虱属(Menoponspp.)、巨羽虱属(Trinoton spp.)、牛羽虱属(Bovicola spp.)、Werneckiella spp.、Lepikentron spp.、畜虱属(Damalina spp.)、嚼虱属(Trichodectes spp.)、猫羽虱属(Felicola spp.)。
双翅目及长角亚目(Nematocerina)和短角亚目(Brachycerina),例如伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culexspp.)、蚋属(Simulium spp.)、真蚋属(Eusimlliumspp.)、白蛉属(Phlebotomus spp.)、罗蛉属(Lutzomyia spp.)、库蠓属(Culicoidesspp.)、斑虻属(Chrysops spp.)、瘤虻属(Hybomitra spp.)、黄虻属(Atylotus spp.)、虻属(Tabanus spp.)、麻虻属(Haematopota spp.)、Philipomyia spp.、蜂虱蝇属(Braula spp.)、家蝇属(Musca spp.)、齿股蝇属(Hydrotaea spp.)、螫蝇属(Stomoxys spp.)、黑角蝇属(Haematobia spp.)、莫蝇属(Morellia spp.)、厕蝇属(Fannia spp.)、舌蝇属(Glossina spp.)、丽蝇属(Cal liphora spp.)、绿蝇属(Luciliaspp.)、金蝇属(Chrysomyia spp.)、污蝇属(Wohlfahrtia spp.)、麻蝇属(Sarcophaga spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypodermaspp.)、胃蝇属(Gasterophilus spp.)、虱蝇属(Hippobosca spp.)、羊虱蝇属(Lipoptena spp.)、蜱蝇属(Melophagus spp.)。
蚤目(Siphonapterida),例如蚤属(Pulex spp.)、栉首蚤属(Ctenocephalides spp.)、客蚤属(Xenopsylla spp.)、角叶蚤属(Ceratophyllus spp.)。
异翅目(Heteropterida),例如臭虫属(Cimex spp.)、锥猎蝽属(Triatoma spp.)、红猎蝽属(Rhodnius spp.)、锥蝽属(Panstrongylusspp.)。
蜚蠊目(Blattarida),例如东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta americana)、德国蠊(Blattela germanica)、夏柏拉蟑螂属(Supella spp.)。
蜱螨亚纲(Acaria、Acarida)及后气门目(Metastigmata)和中气门目(Mesostigmata),例如锐缘蜱属(Argas spp.)、钝缘蜱属(Ornithodorus spp.)、残喙蜱属(Otobius spp.)、硬蜱属(Ixodesspp.)、花蜱属(Amblyomma spp.)、牛蜱属(Boophilus spp.)、革蜱属(Dermacentor spp.)、Haemophysalis spp.、璃眼蜱属(Hyalommaspp.)、扇头蜱属(Rhipicephalus spp.)、皮刺螨属(Dermanyssus spp.)、刺利螨属(Raillietia spp.)、肺刺螨属(Pneumonyssus spp.)、胸刺螨属(Sternostoma spp.)、蜂螨属(Varroa spp.)。
轴螨目(Actinedida)(前气门亚目(Prostigmata))和粉螨目(Acaridida)(无气门亚目(Astigmata)),例如蜂盾螨属(Acarapisspp.)、姬螯螨属(Cheyletiella spp.)、禽螯螨属(Ornithocheyletiaspp.)、肉螨属(Myobia spp.)、疮螨属(Psorergates spp.)、蠕形螨属(Demodex spp.)、恙螨属(Trombicula spp.)、Listrophorus spp.、粉螨属(Acarus spp.)、食酪螨属(Tyrophagus spp.)、嗜木螨属(Caloglyphus spp.)、颈下螨属(Hypodectes spp.)、翅螨属(Pterolichus spp.)、痒螨属(Psoroptes spp.)、皮螨属(Chorioptesspp.)、耳疥螨属(Otodectes spp.)、疥螨属(Sarcoptes spp.)、耳螨属(Notoedres spp.)、疙螨属(Knemidocoptes spp.)、气囊螨属(Cytodites spp.)、鸡雏螨属(Laminosioptes spp.)。
本发明式(I)的活性化合物也适用于防治侵袭农业生产性家畜的节肢动物,所述农业生产性家畜,包括例如牛、绵羊、山羊、马、猪、驴、骆驼、水牛、兔、家鸡、火鸡、鸭、鹅、蜜蜂,其它宠物类,例如狗、猫、笼鸟和观赏鱼,以及所谓的试验性动物,例如仓鼠、豚鼠、大鼠和小鼠。通过防治所述节肢动物,将会减少死亡率和产量(肉、奶、毛、皮、蛋、蜜等)的降低,从而通过使用本发明活性化合物可使畜牧更经济和更简便。
本发明活性化合物以已知方式用于兽医领域和畜牧业中,通过例如片剂、胶囊剂、饮剂、兽用顿服药、颗粒剂、膏剂、丸剂、喂服(feed-through)法、栓剂的方式进行肠内给药,通过例如注射(肌内、皮下、静脉内、腹膜内等)、植入进行肠胃外给药,通过鼻部给药,通过例如浸渍或沐浴(bathing)、喷雾、浇注(pouring on)和点滴、清洗和撒粉的形式,以及借助于含有活性化合物的模型制品例如项圈、耳标、尾标、肢体缚带(limb band)、笼头、标识器等进行皮肤给药。
用于家畜、家禽、宠物等动物时,式(I)的活性化合物可作为含有1-80重量%的活性化合物的制剂(例如粉剂、乳剂、可流动剂)直接使用或稀释100-10000倍后使用,或者它们可作为化学浴剂使用。
此外已发现本发明化合物对毁坏工业材料的昆虫具有强杀虫作用。
以下昆虫可作为实例和优选——但不受任何限制——而提及:
甲虫,例如北美家天牛(Hylotrupes bajulus)、Chlorophoruspilosis、家具窃蠹(Anobium punctatum)、报死窃蠹(Xestobiumrufovillosum)、梳角细脉窃蠹(Ptilinuspecticornis)、Dendrobiumpertinex、松窃蠹(Ernobius mollis)、Priobium carpini、褐粉蠹(Lyctus brunneus)、非洲粉蠹(Lyctus africanus)、南方粉蠹(Lyctusplanicollis)、栎粉蠹(Lyctus linearis)、柔毛粉蠹(Lyctuspubescens)、Trogoxylon aequale鳞毛粉蠹(Minthes rugicollis)、材小蠹种(Xyleborus spec.)、Tryptodendron spec.、咖啡黑长蠹(Apatemonachus)、槲长蠹(Bostrychus capucins)、褐异翅长蠹(Heterobostrychus brunneus)、棘长蠹种(Sinoxylon spec.)、竹长蠹(Dinoderus minutus);
膜翅目昆虫(Hymenopteron),例如大树蜂(Sirex juvencus)、枞大树蜂(Urocerus gigas)、泰加大树蜂(Urocerus gigas taignus)、Urocerus augur;
白蚁,例如欧洲木白蚁(Kalotermes flavicollis)、麻头堆砂白蚁(Cryptotermes brevis)、灰点异白蚁(Heterotermes indicola)、欧美散白蚁(Reticulitermes flavipes)、桑特散白蚁(Reticulitermessantonensis)、南欧网纹白蚁(Reticulitermes lucifugus)、达尔文澳白蚁(Mastotermes darwiniensis)、内华达古白蚁(Zootermopsisnevadensis)、家白蚁(Coptotermes formosanus);
蠹虫(Bristletail),例如衣鱼(Lepisma saccharina)。
本说明书中工业材料的含义应理解为非活体(non-living)材料,例如,优选塑料、粘合剂、胶料、纸张和纸板、皮革、木材、经加工的木材制品和涂料组合物。
即用组合物如果合适可含有其它杀昆虫剂,并且如果合适还可含有一种或多种杀真菌剂。
关于其它可能的添加剂,可参见以上提及的杀虫剂和杀真菌剂。
本发明化合物同样可施用于保护与海水或微咸水接触的物体,特别是船体、筛、网、建筑物、码头及信号系统,以防污染。
此外,本发明化合物可单独或与其它活性化合物结合用作防污剂。
在家用、卫生和贮存产品保护中,本发明活性化合物还适于防治密闭空间内的动物有害物,特别是昆虫、蛛形纲动物和螨虫,所述密闭空间例如住所、工厂车间、办公室、交通工具舱室等。它们可单独或与其它活性化合物及助剂相结合用于家用杀虫产品中以防治所述害虫。它们对敏感及抗性物种以及对全部发育阶段均有效。所述害虫包括:
蝎目(Scorpionidea),例如地中海黄蝎(Buthus occitanus)。
蜱螨目,例如波斯锐缘蜱(Argaspersicus)、鸽锐缘蜱(Argasreflexus)、苔螨亚种(Bryobia ssp.)、鸡皮刺螨、家嗜甜螨(Glyciphagus domesticus)、非洲钝缘蜱(Ornithodorus moubat)、血红扇头蜱(Rhipicephalus sangu ineus)、阿氏真恙螨(Trombiculaalfreddugesi)、Neutrombicula autumnalis、特嗜皮螨(Dermatophagoides pteronissimus)、法嗜皮螨(Dermatophagoidesforinae)。
蜘蛛目(Araneae),例如捕鸟蛛(Aviculariidae)、圆蛛(Araneidae)。
盲蛛目(Opiliones),例如螯蝎(Pseudoscorpiones chelifer)、Pseudoscorpiones cheiridium、长踦盲蛛(Opiliones phalangium)。
等足目,例如栉水虱、球鼠妇。
倍足目,例如Blaniulus guttulatus、山蛩虫属(Polydesmus spp.)。
唇足目,例如地蜈蚣属。
衣鱼目(Zygentoma),例如栉衣鱼属(Ctenolepisma spp.)、衣鱼、盗火虫(Lepismodes inquilinus)。
蜚蠊目,例如东方蜚蠊、德国蠊、亚洲蠊(Blattella asahinai)、马德拉蜚蠊、角腹蠊属(Panchlora spp.)、木蠊属(Parcoblatta spp.)、澳洲大蠊(Periplaneta australasiae)、美洲大蠊、大褐大蠊(Periplaneta brunnea)、烟色大蠊(Periplaneta fuliginosa)、棕带蜚蠊(Supella longipalpa)。
跳跃目(Saltatoria),例如家蟋。
革翅目,例如欧洲球螋。
等翅目,例如木白蚁属(Kalotermes spp.)、散白蚁属。
啮虫目(Psocoptera),例如Lepinatus spp.、粉啮虫属(Liposcelisspp.)。
鞘翅目(Coleptera),例如圆皮蠹属、毛皮蠹属、皮蠹属、长头谷盗(Latheticus oryzae)、隐跗郭公虫属(Necrobia spp.)、蛛甲属、谷蠹、谷象(Sitophilus granarius)、米象(Sitophilus oryzae)、玉米象(Sitophilus zeamais)、药材甲(Stegobium paniceum)。
双翅目,例如埃及伊蚊(Aedes aegypti)、白纹伊蚊(Aedesalbopictus)、带喙伊蚊(Aedes taeniorhynchus)、按蚊属、红头丽蝇、高额麻虻(Chrysozona pluvialis)、五带淡色库蚊(Culexquinquefasciatus)、尖音库蚊(Culex pipiens)、环喙库蚊(Culextarsalis)、果蝇属(Drosophila spp.)、夏厕蝇(Fannia canicularis)、家蝇(Musca domestica)、白蛉属、肉蝇(Sarcophaga carnaria)、蚋属、厩螫蝇(Stomoxys calcitrans)、欧洲大蚊。
鳞翅目,例如小蜡螟(Achroia grisella)、大蜡螟、印度谷螟(Plodia interpunctella)、木塞谷蛾(Tinea cloacella)、袋谷蛾、幕谷蛾。
蚤目,例如犬栉首蚤(Ctenocephalides canis)、猫栉首蚤(Ctenocephalides felis)、人蚤(Pulex irritans)、穿皮潜蚤(Tungapenetrans)、印鼠客蚤。
膜翅目,例如广布弓背蚁(Camponotus herculeanus)、黑臭蚁(Lasius fuliginosus)、黑蚁(Lasius niger)、Lasius umbratus、小家蚁、Paravespula spp.、铺道蚁(Tetramorium caespitum)。
虱目(Anoplura),例如头虱(Pediculus humanus capitis)、体虱(Pediculus humanus corporis)、Pemphigus spp.、Phylloeravastatrix、阴虱(Phthirus pubis)。
异翅目,例如热带臭虫(Cimex hemipterus)、温带臭虫(Cimexlectularius)、长红猎蝽(Rhodinus prolixus)、侵扰锥猎蝽(Triatomainfestans)。
在家用杀昆虫剂领域中,它们可单独地或与其它适宜的活性化合物结合使用,所述适宜的活性化合物例如磷酸酯类、氨基甲酸酯类、拟除虫菊酯类、新烟碱类、生长调节剂或其它已知杀昆虫剂类活性化合物。
它们可以以下形式作为颗粒剂或粉末剂用于抛撒的饵料中或毒饵站(bait station)中使用:气雾剂、无压喷雾产品,例如泵喷雾和雾化器喷雾、自动雾化系统、雾化剂、泡沫剂、凝胶剂;具有由纤维素或聚合物制得的蒸发片的蒸发产品,液态蒸发剂、凝胶和膜蒸发剂,推进剂驱动的蒸发剂,无动力或无源蒸发系统;捕蛾纸、捕蛾袋和捕蛾胶。
本发明活性化合物也可用作脱叶剂、干燥剂、除茎叶剂(haulmkiller),特别是用作除杂草剂。广义的杂草的含义应理解为在不需要它们的地方生长的所有植物。本发明物质用作非选择性还是选择性除草剂,主要取决于施用率。
本发明活性化合物可用在例如以下植物中:
以下属的双子叶杂草:白麻属(Abutil on)、苋属(Amaranthus)、豚草属(Ambrosia)、Anoda、春黄菊属(Anthemis)、Aphanes、滨藜属(Atriplex)、雏菊属(Bellis)、鬼针属(Bidens)、荠属(Capsella)、飞廉属(Carduus)、决明属(Cassia)、矢车菊属(Centaurea)、藜属(Chenopodium)、蓟属(Cirsium)、旋花属(Convolvulus)、曼陀罗属(Datura)、山蚂蝗属(Desmodium)、刺酸模属(Emex)、糖芥属(Erysimum)、大戟属(Euphorbia)、鼬瓣花属(Galeopsis)、牛膝菊属(Galinsoga)、拉拉藤属(Galium)、芙蓉属(Hibiscus)、番薯属(Ipomoea)、地肤属(Kochia)、野芝麻属(Lamium)、独行菜属(Lepidium)、母草属(Lindernia)、母菊属(Matricaria)、薄荷属(Mentha)、山靛属(Mercurialis)、Mullugo、勿忘我属(Myosotis)、罂粟属(Papaver)、牵牛属(Pharbitis)、车前属(Plantago)、蓼属(Polygonum)、马齿苋属(Portulaca)、毛茛属(Ranunculus)、萝卜属(Raphanus)、蔊菜属(Rorippa)、节节菜属(Rotala)、酸模属(Rumex)、猪毛菜属(Salsola)、千里光属(Senecio)、田菁属(Sesbania)、黄花稔属(Sida)、白芥属(Sinapis)、茄属(Solanum)、苦苣菜属(Sonchus)、尖瓣花属(Sphenoclea)、繁缕属(Stellaria)、蒲公英属(Taraxacum)、菥蓂属(Thlaspi)、车轴草属(Trifolium)、荨麻属(Urtica)、婆婆纳属(Veronica)、堇菜属(Viola)、苍耳属(Xanthium)。
以下属的双子叶作物:花生属(Arachis)、甜菜属(Beta)、芸苔属(Brassica)、黄瓜属(Cucumis)、南瓜属(Cucurbita)、向日葵属(Helianthus)、胡萝卜属(Daucus)、大豆属(Glycine)、棉属(Gossypium)、番薯属(Ipomoea)、莴苣属(Lactuca)、亚麻属(Linum)、番茄属(Lycopersicon)、烟草属(Nicotiana)、菜豆属(Phaseolus)、豌豆属(Pisum)、茄属(Solanum)、蚕豆属(Vicia)。
以下属的单子叶杂草:山羊草属(Aegilops)、冰草属(Agropyron)、剪股颖属(Agrostis)、看麦娘属(Alopecurus)、Apera、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属(Bromus)、蒺藜草属(Cenchrus)、鸭跖草属(Commelina)、狗牙根属(Cynodon)、莎草属(Cyperus)、龙爪茅属(Dactyloctenium)、马唐属(Digitaria)、稗属(Echinochloa)、荸荠属(Eleocharis)、蟋蟀草属(Eleusine)、画眉草属(Eragrostis)、野黍属(Eriochloa)、羊茅属(Festuca)、飘拂草属(Fimbristylis)、异蕊花属(Heteranthera)、白茅属(Imperata)、鸭嘴草属(Ischaemum)、千金子属(Leptochloa)、黑麦草属(Lolium)、雨久花属(Monochoria)、黍属(Panicum)、雀稗属(Paspalum)、虉草属(Phalaris)、梯牧草属(Phleum)、早熟禾属(Poa)、筒轴茅属(Rottboellia)、慈姑属(Sagittaria)、莞草属(Scirpus)、狗尾草属(Setaria)、高粱属(Sorghum)。
以下属的单子叶作物:葱属(Allium)、凤梨属(Ananas)、天门冬属(Asparagus)、燕麦属(Avena)、大麦属(Hordeum)、稻属(Oryza)、黍属(Panicum)、甘蔗属(Saccharum)、黑麦属(Secale)、高粱属(Sorghum)、小黑麦属(Triticale)、小麦属(Triticum)、玉蜀黍属(Zea)。
但是,本发明活性化合物的使用决不限于所述属,而是以相同方式推广至其它植物。
依据浓度,本发明活性化合物适于在例如工业地带和铁道以及有树和无树的道路和场所中用于非选择性地防治杂草。本发明活性化合物同样可用于防治多年生作物中的杂草,所述多年生作物例如森林、观赏性树木栽植、果园、葡萄园、柑桔林、坚果园、香蕉种植园、咖啡种植园、茶叶种植园、橡胶种植园、油椰种植园、可可种植园、无核水果(soft fruit)栽植和蛇麻草田(hop field)、草坪、草地和牧场;和用于选择性防治一年生作物中的杂草。
本发明物质在用于土壤和地上植物部位时,具有强的除草活性和很宽的作用谱。在某种程度上,它们还适于选择性防治单子叶和双子叶作物中的单子叶和双子叶杂草,出苗前和出苗后均可。
本发明活性化合物也可以一定浓度或施用率用于防治动物有害物及真菌或细菌植物病害。如果合适,它们还可用作合成其它活性化合物的中间体或前体。
本发明活性化合物可转化为常规制剂,例如溶液、乳剂、可湿性粉剂、悬浮剂、粉剂、粉末剂、膏剂、可溶性粉剂、颗粒剂、悬乳浓缩剂、用活性化合物浸渍过的天然及合成材料,以及聚合物中的微胶囊。
这些制剂以已知方式制备,例如将活性化合物与填充剂混合,即与液体溶剂和/或固体载体混合,同时任选使用表面活性剂,即乳化剂和/或分散剂和/或发泡剂。
如果所用填充剂为水,还可使用例如有机溶剂作为助溶剂。适宜的液体溶剂主要有:芳香族化合物,例如二甲苯、甲苯或烷基萘;氯化芳香族化合物和氯化脂族烃,例如氯苯、氯乙烯或二氯甲烷;脂族烃,例如环己烷或石蜡,如石油馏分、矿物油和植物油;醇,例如丁醇或乙二醇,及其醚和酯;酮,例如丙酮、甲乙酮、甲基异丁基酮或环己酮;强极性溶剂,例如二甲基甲酰胺和二甲基亚砜;以及水。
适宜的固体载体有:例如铵盐和粉碎的天然矿物,例如高岭土、粘土、滑石、白垩、石英、凹凸棒石、蒙脱石或硅藻土,以及粉碎的合成矿物,例如细分散二氧化硅、氧化铝和硅酸盐;适用于颗粒剂的固体载体有:例如粉碎并分级的天然岩石,例如方解石、大理石、浮石、海泡石和白云石,以及合成的无机及有机粉颗粒,以及有机物颗粒例如锯木屑、椰壳、玉米穗轴和烟草茎;适宜的乳化剂和/或发泡剂有:例如非离子及阴离子乳化剂,例如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,如烷基芳基聚乙二醇醚,烷基磺酸盐、烷基硫酸盐、芳基磺酸盐及蛋白质水解产物;适宜的分散剂有:例如木素亚硫酸盐废液和甲基纤维素。
制剂中可使用增粘剂,例如羧甲基纤维素以及粉末、颗粒或胶乳形式的天然及合成聚合物,例如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,例如脑磷脂和卵磷脂,以及合成磷脂。其它添加剂可以是矿物油和植物油。
可使用着色剂,例如无机颜料,如氧化铁、氧化钛和普鲁士蓝,以及有机染料,例如茜素染料、偶氮染料和金属酞菁染料,以及微量营养素如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
制剂一般含有0.1和95之间重量百分比活性化合物,优选0.5和90%之间。
本发明活性化合物本身或其制剂也可与已知除草剂和/或与改善作物植物耐受性物质(“安全剂”)混合用于杂草防治目的,可即用混合或桶内混合(tank mix)。由此也可与含有一种或多种已知除草剂和一种安全剂的除草剂产品混合。
适于混合的除草剂为已知除草剂,例如
乙草胺(acetochlor)、三氟羧草醚(acifluorfen(-sodium))、苯草醚(aclonifen)、甲草胺(alachlor)、禾草灭(alloxydim(-sodium))、莠灭净(ametryne)、氨唑草酮(amicarbazone)、先甲草胺(amidochlor)、酰嘧磺隆(amidosulfuron)、氨草啶(aminopyralid)、莎稗磷(anilofos)、磺草灵(asulam)、莠去津(atrazine)、唑啶草酮(azafenidin)、四唑嘧磺隆(azimsulfuron)、氟丁酰草胺(beflubutamid)、草除灵(benazolin(-ethyl))、呋草黄(benfuresate)、苄嘧磺隆(bensulfuron(-methyl))、灭草松(bentazone)、bencarbazone、双苯嘧草酮(benzfendizone)、双环磺草酮(benzobicyclon)、吡草酮(benzofenap)、新燕灵(benzoylprop(-ethyl))、双丙氨膦(bialaphos)、甲羧除草醚(bifenox)、双草醚(bispyribac(-sodium))、溴丁酰草胺(bromobutide)、溴酚污(bromofenoxim)、溴苯腈(bromoxynil)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil(-allyl))、丁苯草酮(butroxydim)、丁草敌(butylate)、唑草胺(cafenstrole)、醌肟草(caloxydim)、双酰草胺(carbetamide)、唑草酯(carfentrazone(-ethyl))、甲氧除草醚(chlomethoxyfen)、草灭畏(chloramben)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron(-ethyl))、草枯醚(chlornitrofen)、氯磺隆(chlorsulfuron)、绿麦隆(chlortoluron)、吲哚酮草酯(cinidon(-ethyl))、环庚草醚(cinmethylin)、醚磺隆(cinosulfuron)、环苯草酮(clefoxydim)、烯草酮(clethodim)、炔草酸(clodinafop(-propargyl))、异恶草松(clomazone)、氯甲酰草胺(clomeprop)、二氯吡啶酸(clopyralid)、clopyrasulfuron(-methyl)、氯酯磺草胺(cloransulam(-methyl))、苄草隆、氰草津(cyanazine)、cybutryne、环草敌(cycloate)、环丙嘧磺隆(cyclosulfamuron)、噻草酮(cycloxydim)、氰氟草酯(cyhalofop(-butyl))、2,4-D、2,4-DB、甜菜安(desmedipham)、燕麦敌(diallate)、麦草畏、精2,4-滴丙酸(dichlorprop(-P))、禾草灵(diclofop(-methyl))、双氯磺草胺(diclosulam)、乙酰甲草胺(diethatyl(-ethyl))、野燕枯(difenzoquat)、吡氟酰草胺(diflufenican)、氟吡草腙(diflufenzopyr)、恶唑隆(dimefuron)、哌草丹、二甲草胺(dimethachlor)、异戊乙净(dimethametryn)、二甲吩草胺(dimethenamid)、dimexyflam、氨氟灵(dinitramine)、双苯酰草胺(diphenamid)、敌草快(diquat)、氟硫草定(dithiopyr)、敌草隆(diuron)、杀草隆、epropodan、EPTC、戊草丹(esprocarb)、乙丁烯氟灵(ethalfluralin)、胺苯磺隆(ethametsulfuron(-methyl))、乙氧呋草黄(ethofumesate)、氟乳醚(ethoxyfen)、乙氧嘧磺隆(ethoxysulfuron)、乙氧苯草胺(etobenzanid)、精恶唑禾草灵(fenoxaprop(-P-ethyl))、四唑酰草胺(fentrazamide)、麦草氟(异丙酯、异丙酯-L、甲酯)(flamprop(-isopropyl,-isopropyl-L,-methyl))、啶嘧磺隆(flazasulfuron)、双氟磺草胺(florasulam)、精吡氟禾草灵(fluazifop(-P-butyl))、异丙吡草酯(fluazolate)、氟酮磺隆(flucarbazone(-sodium))、氟噻草胺(flufenacet)、唑嘧磺草胺(flumetsulam)、氟烯草酸(flumiclorac(-pentyl))、丙炔氟草胺(flumioxazin)、flumipropyn、唑嘧磺草胺(flumetsulam)、氟草隆(fluometuron)、氟咯草酮(fluorochloridone)、乙羧氟草醚(fluoroglycofen(-ethyl))、氟胺草唑(flupoxam)、flupropacil、flurpyrsulfuron(-methyl,-sodium)、芴丁酯(flurenol(-butyl))、氟啶草酮(fluridone)、氯氟吡氧乙酸(-丁氧基丙基,-meptyl)(fluroxypyr(-butoxypropyl,-meptyl))、呋嘧醇(flurprimidol)、呋草酮(flurtamone)、氟噻乙草酯(fluthiacet(-methyl))、fluthiamide、氟磺胺草醚(fomesafen)、甲酰氨磺隆(foramsulfuron)、草铵膦(glufosinate(-ammonium))、草甘膦异丙胺盐(glyphosate(-isopropylammonium)、氟硝磺酰胺(halosafen)、氟吡禾灵(吡氟氯禾灵、精吡氟氯禾灵)(haloxyfop(-ethoxyethyl,-P-methyl))、环嗪酮(hexazinone)、HOK-201、咪草酸(imazamethabenz(-methyl))、imazamethapyr、氧咪草烟(imazamox)、imazapic、咪唑烟酸(imazapyr)、咪唑喹啉酸(imazaquin)、咪唑乙烟酸(imazethapyr)、唑吡嘧磺隆(imazosulfuron)、碘甲磺隆钠盐(iodosulfuron(-methyl,-sodium))、碘苯腈(ioxynil)、异丙乐灵(isopropalin)、异丙隆(isoproturon)、异恶隆(isouron)、异恶酰草胺(isoxaben)、异恶氯草酮(isoxachlortole)、异恶唑草酮(isoxaflutole)、异恶草醚(isoxapyrifop)、乳氟禾草灵(lactofen)、环草定(lenacil)、利谷隆(linuron)、MCPA、2甲4氯丙酸、苯噻酰草胺(mefenacet)、甲基二磺隆(mesosulfurone)、甲基磺草酮(mesotrione)、恶唑酰草胺(metamifop)、苯嗪草酮(metamitron)、吡唑草胺(metazachlor)、甲基苯噻隆(methabenzthiazuron)、吡喃隆(metobenzuron)、溴谷隆(metobromuron)、α-异丙甲草胺((alpha-)metolachlor)、磺草唑胺(metosulam)、甲氧隆(metoxuron)、嗪草酮(metribuzin)、甲磺隆(metsulfuron(-methyl))、禾草敌(molinate)、绿谷隆(monolinuron)、萘丙胺(naproanilide)、敌草胺(napropamide)、草不隆(neburon)、烟嘧磺隆(nicosulfuron)、氟草敏(norflurazon)、坪草丹(orbencarb)、嘧苯胺磺隆(orthosulfamuron)、氨磺乐灵(oryzalin)、丙炔恶草酮(oxadiargyl)、恶草酮(oxadiazon)、环氧嘧磺隆(oxasulfuron)、恶嗪草酮(oxaziclomefone)、乙氧氟草醚(oxyfluorfen)、百草枯(paraquat)、壬酸(pelargonic acid)、二甲戊灵(pendimethalin)、pendralin、penoxsulam、环戊恶草酮(pentoxazone)、甜菜宁(phenmedipham)、氟吡酰草胺(picolinafen)、pinoxaden、哌草磷(piperophos)、丙草胺(pretilachlor)、氟嘧磺隆(primisulfuron(-methyl))、氟唑草胺(profluazol)、扑草净(prometryn)、毒草胺(propachlor)、敌稗(propanil)、恶草酸(propaquizafop)、异丙草胺(propisochlor)、propoxycarbazone(-sodium)、pyroxsulam、炔苯酰草胺(propyzamide)、苄草丹(prosulfocarb)、氟磺隆(prosulfuron)、吡草醚(pyraflufen(-ethyl))、pyrasulfotole、双唑草腈(pyrazogyl)、吡唑特(pyrazolate)、吡嘧磺隆(pyrazosulfuron(-ethyl))、苄草唑(pyrazoxyfen)、嘧啶肟草醚(pyribenzoxim)、稗草丹(pyributicarb)、哒草特(pyridate)、pyridatol、环酯草醚(pyriftalide)、嘧草醚(pyriminobac(-methyl))、pyrimisulfan、嘧草硫醚(pyrithiobac(-sodium))、pyroxasulfone、二氯喹啉酸(quinchlorac)、氯甲喹啉酸(quinmerac)、灭藻醌(quinoclamine)、喹禾灵(精喹禾灵、喹禾糖酯)(quizalofop(-P-ethyl,-P-tefuryl))、砜嘧磺隆(rimsulfuron)、烯禾啶(sethoxydim)、西玛津(simazine)、西草净(simetryn)、磺草酮(sulcotrione)、甲磺草胺(sulfentrazone)、甲嘧磺隆(sulfometuron(-methyl))、草甘膦(sulfosate)、磺酰磺隆(sulfosulfuron)、牧草胺(tebutam)、丁噻隆(tebuthiuron)、tembotrione、tepraloxydim、特丁津(terbuthylazine)、特丁净(terbutryn)、噻吩草胺(thenylchlor)、thiafluamide、噻唑烟酸(thiazopyr)、噻二唑草胺(thidiazimin)、thiencarbazone-methyl、噻吩磺隆(thifensulfuron(-methyl))、禾草丹(thiobencarb)、仲草丹(tiocarbazil)、topramezone、三甲苯草酮(tralkoxydim)、野燕畏(triallate)、醚苯磺隆(triasulfuron)、苯磺隆(tribenuron(-methyl))、三氯吡氧乙酸(triclopyr)、灭草环(tridiphane)、氟乐灵(trifluralin)、三氟啶磺隆(trifloxysulfuron)、氟胺磺隆(triflusulfuron(-methyl))、三氟甲磺隆(tritosulfuron)和
也可与其它已知活性化合物例如杀真菌剂、杀昆虫剂、杀螨虫剂、杀线虫剂、驱鸟剂、植物营养素及土壤改良剂混合。
本发明活性化合物或活性化合物结合物可以其本身、其制剂形式或由其制备的使用形式通过进一步稀释而施用,例如即用溶液、悬浮剂、乳剂、粉剂、膏剂和颗粒剂。它们以常规方式施用,例如浇注、喷雾、雾化、抛撒(spreading)。
本发明活性化合物或活性化合物结合物既可在植物出苗前也可在植物出苗后施用。还可将它们在种植前掺入土壤中。
活性化合物的施用率可在非常宽的范围内变化,主要取决于所需效果的特征。一般而言,施用率介于1g至10kg活性化合物/公顷土壤面积之间,优选介于5g至5kg活性化合物/公顷之间。
活性化合物结合物与作物植物相容性的有利效果在某些浓度比例时特别显著。但是,活性化合物结合物中各活性化合物的重量比可在相对宽泛的范围内变化。一般而言,每重量份式(I)活性化合物使用0.001-1000重量份、优选0.01-100重量份、特别优选0.05-20重量份以上提及的从属于(b')的改进作物植物相容性的一种化合物的盐。
本发明活性化合物结合物通常以制得的制剂的形式施用。但是,活性化合物结合物中所含的活性化合物可以单个的制剂施用,也可在使用过程中进行混合,即以桶内混合物的形式施用。
对于某些施用,特别是通过出苗后方法进行施用,制剂中可更有利地包括植物耐受性矿物油或植物油(例如市售制剂“Rako Binol”),或铵盐如硫酸铵或硫代氰酸铵作为其它添加剂。
本发明的新的活性化合物结合物可以其本身、其制剂形式或由所述制剂通过进一步稀释制得的使用形式使用,例如即用溶液剂、悬浮剂、乳剂、粉剂、膏剂和颗粒剂。可以通过常规方式施用,例如浇灌、喷雾、弥雾、撒粉或散播。
本发明活性化合物结合物的施用率可在一定范围内变化;这尤其取决于气候及土壤因素。一般而言,施用率在0.001和5kg/ha之间,优选0.005和2kg/ha之间,特别优选0.01和0.5kg/ha之间。
本发明活性化合物结合物可植物出苗前或其出苗后施用,即通过出苗前方法和出苗后方法施用。
根据安全剂的特性,本发明所用安全剂可用于预处理作物植物的种子(拌种)或可播种前引入播种沟(seed furrow)或者在植物出苗前或出苗后在除草剂之前单独使用或与除草剂一起使用。
可提及的植物的实例为重要的作物植物,例如谷类(小麦、大麦、稻)、玉米、大豆、马铃薯、棉花、油菜、甜菜、甘蔗以及果树(果实有苹果、梨、柑橘类水果及葡萄),特别强调的是谷类、玉米、大豆、马铃薯、棉花及油菜。
在每一种情况下,术语“活性化合物”还包括本文提及的活性化合物结合物。
本发明活性化合物的制备和用途通过以下实例进行示例说明。
制备实施例
实施例I-a-1和I-a-2
首先将2.50g(7.9mmol)反-2-[(2-乙基-4,6-二甲基苯基)乙酰基]环己烷甲酸甲酯和1.77g叔丁醇钾(15.8mmol)加入20ml无水二甲基甲酰胺中,并将混合物在50℃加热3h。冷却后,将混合物加入冰水中,用2N盐酸酸化至pH2并用乙酸乙酯萃取。将有机相用水洗涤两次、干燥(硫酸镁)并用旋转蒸发仪浓缩。剩余物使用己烷/乙酸乙酯(v/v=60:40)在硅胶上进行色谱分离。
级分A:反式异构体I-a-1
产率:0.94g(42%)
熔点:196-197℃
级分B:顺式异构体I-a-2
产率:0.60g(27%)
熔点:220-221℃
实施例I-b-1
将0.13g(1.2mmol)异丁酰氯添加至含有0.300g(1.0mmol)反-2-[(2-乙基-4,6-二甲基苯基)-3-羟基六氢-1H-茚-1-酮的0.5ml氯仿和5ml三乙胺中,并且在室温下搅拌1h后,将混合物倒入冰中。将混合物加入氯仿中,用水和稀盐酸洗涤,然后干燥(硫酸镁)并用旋转蒸发仪浓缩。随后用硅胶进行色谱分离(乙酸乙酯/己烷的v/v=70:30),得到无色油状所需产物0.31g(83%)。
1H-NMR(400MHz,CDCl3):δ=1.10(d,6H),2.42(mc,2H),2.62(mc,2H),2.98(mc,1H),6.82-6.90(m,2H)ppm
实施例I-b-2
将133mg(0.6mmol)间氯过苯甲酸添加至0.2g(0.54mmol)实施例I-b-43的化合物与2ml0.5M碳酸氢钠溶液在10ml二氯甲烷中的混合物中,并将混合物在室温下搅拌2h。然后将混合物溶于(takeup)30ml二氯甲烷中,用10%浓度的碳酸钾溶液和水洗涤,干燥(硫酸镁)并用旋转蒸发仪浓缩。用硅胶进行色谱分离(乙酸乙酯/己烷的v/v=80:20),得到0.12g(58%)无色油状所需产物(异构体混合物)。
1H-NMR(400MHz,CDCl3):δ=2.67(d,br,1H),2.75(mc,1H),3.20(mc,1H),3.27(mc,1H),3.33(s,3H),4.07(s,2H)ppm。
实施例I-c-1
将75mgg(0.7mmol)氯甲酸乙酯添加至含有0.200g(0.7mmol)反-2-[(2-乙基-4,6-二甲基苯基)-3-羟基六氢-1H-茚-1-酮(实施例I-a-1)的5ml氯仿和0.5ml三乙胺中,并将混合物在室温下搅拌1h。将混合物用约30ml氯仿进行稀释,转移到分液漏斗中并相继用水、2N盐酸、再次用水洗涤,干燥(硫酸镁),蒸馏除去溶剂后,在硅胶上进行色谱分离(乙酸乙酯/己烷的v/v=90:10)。得到0.21g(84%)无色油状目标化合物。
1H-NMR(400MHz,CDCl3):δ=1.08(t,3H),1.13(t,3H),2.62(mc,1H),3.01(mc,1H),4.18(q,2H),6.90(mc,2H)ppm。
实施例I-e-1
(参见实施例I-c-1)
以类似方式(参见实施例I-c-1),使用0.30g(1mmol)顺-2-(乙基-4,6-二甲基苯基)-3-羟基六氢-1H-茚-1-酮和0.18g(1mmol)二乙基磷酰氯,经柱层析(乙酸乙酯/己烷v/v=85:15)之后,得到0.29g(65%)无色油状标题化合物。
1H-NMR(300MHz,CDCl3):δ=1.08-1.20(m,9H),mc=1.95(mc,2H),2.10和2.25(各自为s,各自为3H),2.82(mc,1H),3.65-3.92(m,4H),6.85(mc,2H)ppm。
实施例II-1
(XVI-1) (XVII-1) (XIII-1) 反式(II-1)
顺式或反式
在-30℃,将9.0g(43.6mmol)2-乙基-4,6-二甲基苯基乙酸甲酯缓慢地逐滴加入至2,2,6,6-四甲基哌啶锂的溶液中,该溶液由15.4g(109mmol)2,2,6,6-四甲基哌啶的80ml THF溶液和43.7ml(109mmol)2.5M正丁基锂的己烷溶液制得;并将混合物在室温下再搅拌30min。然后,在-20℃,添加6.7g(43.6mmol)溶解在20ml THF中的环己烷-1,2-二甲酸酐,并将该混合物在室温下搅拌12h。添加50ml饱和的氯化铵溶液,用乙酸乙酯萃取,用水洗涤萃取液,干燥(硫酸镁)并用旋转蒸发仪浓缩,得到约10g固体,向该固体添加12mg氢氧化钾的100ml水的溶液,并将该混合物加热回流24h。然后将该混合物用2N盐酸酸化至pH为2,通过抽吸过滤出固体。得到5.3g(40%)淡黄色固态2-[2-乙基-4,6-二甲基苯基)乙酰基]环己烷甲酸,其可无需进一步纯化而用于下一反应步骤中。
将5.0g(16.5mmol)该中间体的30ml丙酮溶液与2g碳酸钾和5g(35mmol)碘代甲烷一起在回流状态下煮沸4h,然后溶于(takeup)乙酸乙酯中,与水一起摇振并干燥(硫酸镁),并将溶剂蒸馏掉。使用乙酸乙酯/己烷(v/v=80:20)进行硅胶层析,得到2.69(52%)无色晶体形式的所需2-[2-乙基-2,6-二甲基苯基)乙酰基]环己烷甲酸甲酯。
1H-NMR(400MHz,CDCl3):δ=1.17(t,3H),2.17和2.26(各自为t,各自为3H),2.48(q,2H),2.72(mc,1H),2.88(mc,1H),3.60(s,3H),3.93(AB体系,2H),6.94和6.97(各自为s,各自为1H)ppm。
方法(A)所需的式(II)化合物类似于实施例(II-1)并根据概述而获得。
式(II)化合物还可通过以下所述方法而获得:
在室温下,将1.5ml四氧化锇溶液(2.5M叔丁醇溶液)、860mgN-甲基氧化吗啉(NMO)和2.0g(6.0mmol)6-[2,6-二乙基-4-甲基苯基)乙酰基]环己-3-烯甲酸甲酯于15ml丙酮中搅拌12h。添加700mg连二亚硫酸钠,并将该混合物在室温下搅拌30min,然后用乙酸乙酯萃取。干燥(硫酸镁)并用旋转蒸发仪浓缩后,剩余约1.8g粘稠的油状物,将该油状物溶于(take up)5ml二甲氧基丙烷,并在添加20g对甲苯磺酸后,在室温下搅拌8h。然后将反应混合物用10%浓度的碳酸钾水溶液洗涤,干燥(硫酸镁)并用旋转蒸发仪浓缩。得到1.05g化合物(II-5)。
1H-NMR(300MHz,CDCl3):δ=1.45(s,3H),1.52(s,3H),2.88(mc,1H),3.20(mc,1H),3.39(mc,1H)ppm。
测试说明
实施例A
1.除草剂出苗前作用
将单子叶和双子叶杂草及作物植物的种子放入木纤维盆中的砂壤土中并用土覆盖。然后将配制成可湿性粉剂(WP)的试验化合物以添加了0.2%湿润剂的水悬浮剂的形式以6001/ha的水施用率(换算的)施用于覆盖土壤的表面。
处理后,将盆置于温室中并保持在对试验植物而言良好的生长条件下。在3周试验期之后,通过与未处理的对照植株进行比较,目视评估对试验植株的损害(除草活性以百分比(%)计:100%活性=植株均死亡,0%活性=与对照植株相同)。
2.除草剂出苗后作用
将单子叶和双子叶杂草及作物植物的种子放入木纤维盆中的砂壤土中,用土壤覆盖并在温室中在良好的生长条件下培育。播种2-3周后,在一叶期对试验植株进行处理。然后将配制成可湿性粉剂(WP)的试验化合物以添加了0.2%湿润剂的形式以6001/ha的水施用率(换算的)喷洒在植株的绿色部位上。将试验植株在温室中在最适宜的生长条件下保持约3周后,通过与未处理的对照植株相比较,目视评估制剂的活性(除草剂活性以百分比(%)计:100%活性=植株均死亡,0%活性=与对照植株相同)。
通过所述出苗前方法以320g活性成分/ha施用时,以下化合物对燕麦(Avena sativa)、多花黑麦草(Lolium multiflorum)和狗尾草(Setaria viridis)表现出≥80%的活性:
I-a-2,I-a-8,I-a-9,I-a-10,I-a-11,I-a-14,I-b-10,I-b-12,I-b-13,I-b-14,I-b-15,I-b-16,I-b-21,I-b-25,I-b-27,I-b-28,I-b-33,I-b-34,I-b-36,I-b-43,I-b-44,I-b-50,I-b-52,I-b-54,I-c-1,I-c-4,I-c-5,I-c-8,I-c-9,I-c-12,I-c-14,I-e-16。
通过所述出苗前方法以320g活性成分/ha施用时,以下化合物对大穗看麦娘(Alopecurus myosuroides)、稗草(Echinocloa crus-gali)、多花黑麦草和狗尾草表现出≥80%的活性:
I-a-18,I-a-20,I-a-21,I-a-24,I-a-25,I-a-26,I-a-27,I-b-55,I-b-56,I-b-57,I-b-59,I-b-60,I-b-73,I-b-76,I-b-77,I-b-78,I-b-79,I-b-80,I-b-81,I-b-82,I-b-83,I-c-19,I-c-23,I-c-24,I-c-25,I-c-26,I-e-17,I-e-18。
通过所述出苗后方法以320g活性成分/ha施用时,以下化合物对燕麦、多花黑麦草和狗尾草表现出≥80%的活性:
I-a-1,I-a-2,I-a-8,I-a-9,I-a-10,I-a-12,I-a-13,I-a-14,I-a-15,I-a-16,I-b-4,I-b-9,I-b-10,I-b-11,I-b-12,I-b-14,I-b-15,I-b-16,I-b-17,I-b-18,I-b-19,I-b-21,I-b-22,I-b-24,I-b-25,I-b-26,I-b-27,I-b-28,I-b-30,I-b-32,I-b-33,I-b-34,I-b-35,I-b-36,I-b-37,I-b-38,I-b-39,I-b-40,I-b-42,I-b-43,I-b-44,I-b-45,I-b-46,I-b-47,I-b-50,I-b-51,I-b-52,I-b-53,I-b-54,I-c-3,I-c-4,I-c-5,I-c-7,I-c-8,I-c-9,I-c-11,I-c-12,I-c-13,I-c-14,I-c-15,I-c-17,I-c-18,I-e-13,I-e-16。
通过所述出苗后方法以320g活性成分/ha施用时,以下化合物对多花黑麦草、狗尾草和稗草表现出≥90%的活性:
I-a-3,I-a-4,I-a-11,I-b-1,I-b-2,I-b-5,I-b-8,I-b-13,I-b-20,I-b-23,I-b-31,I-c-6,I-c-16,I-e-12。
通过所述出苗后方法以80g活性成分/ha施用时,以下化合物对稗草、多花黑麦草和狗尾草表现出≥90%的活性:
I-a-18,I-a-19,I-a-22,I-a-24,I-a-25,I-a-26,I-a-27,I-b-56,I-b-57,I-b-59,I-b-62,I-b-63,I-b-66,I-b-67,I-b-68,I-b-71,I-b-72,I-b-73,I-b-74,I-b-76,I-b-77,I-b-78,I-b-79,I-b-80,I-b-81,I-b-82,I-b-83,I-c-21,I-c-22,I-c-23,I-c-25,I-c-26。
实施例B
除草剂出苗后作用
将单子叶和双子叶杂草及作物植物的种子放入木纤维盆或塑料盆中的砂壤土中,用土覆盖并在温室中在良好生长条件下培育,在生长期期间,也在温室外进行户外培育。播种2-3周后,在一叶至三叶期对试验植株进行处理。将配制成可润湿粉剂(WP)或液剂(EC)的试验化合物添加湿润剂(0.2%-0.3%)后以多种剂量以3001/ha(换算的)的水施用率喷洒至植株和土壤表面。试验植株处理之后3-4周,通过与未经处理的对照植株相比,目视评估制剂的活性(除草剂活性以百分比(%)计:100%活性=植物均死亡,0%活性=与未处理的对照相同)。
使用安全剂
如果另外测试关于安全剂是否可改进作物植物对试验物质的植物相容性,则选用以下方法施用安全剂:
-将作物植物的种子在播种之前用安全剂物质拌种(安全剂的量基于种子的重量以百分比表述)
-在施用试验物质之前,用安全剂以每公顷一定的施用率喷洒作物植物(通常在施用试验物质之前1天)
-将安全剂与试验物质以桶混制剂的形式一起施用(安全剂的量以g/ha表述,或基于除草剂以比例表述)。
通过比较试验物质在有或没有安全剂处理的情况下的效果,可评价安全剂物质的活性。
温室中谷类的容器试验
施用除草剂之前1天施用吡咯二酸(mefenpyr)
表 施用之后28天
表 施用之后28天
表 施用之后28天
表 施用之后28天
表 施用之后28天
表 施用之后28天
表 施用之后28天
表 施用之后28天
表 施用之后28天
表 施用之后28天
表 施用之后28天
表 施用之后28天
表 施用之后10天
表 施用之后10天
表 施用之后10天
表 施用之后10天
表 施用之后10天 施用之后28天
表 施用之后10天
表 施用之后10天
表 施用之后10天
表 施用之后28天
表 施用之后10天
表 施用之后10天
表 施用之后28天
表 施用之后10天
同已知于WO01/74780*的I-6-a-1和I-6-b-1的化合物相比,本发明化合物,例如当通过出苗后方法施用时,表现出显著更好的活性。
实施例C
桃蚜(Myzus)试验(MYZUPE喷洒处理)
溶剂: 78重量份丙酮
1.5重量份二甲基甲酰胺
乳化剂:0.5重量份烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份活性化合物与所述量的溶剂和乳化剂混合,并用含乳化剂的水将浓液稀释至所需浓度。
将被所有阶段的桃蚜(Myzus persicae)侵染的甘蓝(Brassicapekinensis)的圆叶片用所需浓度的活性化合物制剂进行喷洒。
经所需时间段之后,确定以%计的活性。100%意指所有的蚜虫被杀死;0%意指没有蚜虫被杀死。
本试验中,例如,制备实施例的以下化合物在500g/ha的施用率下显示出≥90%的活性:
I-a-2,I-a-3,I-a-18,I-a-20,I-a-22,I-b-1,I-b-14,I-b-15,I-b-16,I-b-17,I-b-18,I-b-21,I-b-22,I-b-25,I-b-51,I-b-52,I-b-55,I-b-56,I-b-57,I-b-58,I-b-59,I-b-60,I-b-61,I-b-63,I-b-67,I-b-71,I-b-72,I-c-1,I-c-4,I-c-5,I-c-7,I-c-19,I-c-22。
实施例D
叶螨属(Tetranychus)试验;OP抗性/喷洒处理(TETRUR)
溶剂: 78重量份丙酮
1.5重量份二甲基甲酰胺
乳化剂: 0.5重量份烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份活性化合物与所述量的溶剂和乳化剂混合,并用含乳化剂的水将浓液稀释至所需浓度。
将被所有阶段的温室红叶螨(Tetranychus urticae)侵染的菜豆叶(Phaseolus vulgaris)的圆叶片用所需浓度的活性化合物制剂进行喷洒。
经所需时间段之后,确定以%计的活性。100%意指所有的螨虫被杀死;0%意指没有螨虫被杀死。
本试验中,例如,制备实施例的以下化合物在100g/ha的施用率下显示出≥90%的活性:
I-a-1,I-a-2,I-a-3,I-a-11,I-a-18,I-a-20,I-a-22,I-a-23,I-b-1,I-b-9,I-b-10,I-b-11,I-b-14,I-b-15,I-b-17,I-b-18,I-b-19,I-b-21,I-b-23,I-b-25,I-b-26,I-b-29,I-b-30,I-b-31,I-b-35,I-b-37,I-b-55,I-b-56,I-b-57,I-b-58,I-b-59,I-b-60,I-b-64,I-b-67,I-b-70,I-b-75,I-b-76,I-b-77,I-b-78,I-b-79,I-b-80,I-b-83,I-b-42,I-c-3,I-c-4,I-c-5,I-c-10,I-c-19,I-c-22,I-c-24,I-c-25,I-c-27,I-e-17。
实施例E
甲虫(Phaedon)试验(PHAECO喷洒处理)
溶剂:78重量份丙酮
1.5重量份二甲基甲酰胺
乳化剂:0.5重量份烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份活性化合物与所述量的溶剂和乳化剂混合,并用含乳化剂的水将浓液稀释至所需浓度。
将甘蓝(Brassica pekinensis)的圆叶片用所需浓度的活性化合物制剂进行喷洒,干燥之后,接种芥菜甲虫(Phaedon cochleariae)的幼虫。
经所需时间段之后,确定以%计的活性。100%意指所有的甲虫幼虫被杀死;0%意指没有甲虫幼虫被杀死。
本试验中,例如,制备实施例的以下化合物在500g/ha的施用率下显示出≥80%的活性:
I-a-1,I-a-2,I-a-3,I-a-15,I-a-20,I-a-21,I-a-22,I-b-14,I-b-15,I-b-16,I-b-17,I-b-18,I-b-19,I-b-21,I-b-22,I-b-55,I-b-61,I-b-67,I-b-71,I-c-1,I-c-4,I-c-5,I-c-19,I-c-22。
实施例F
微小牛蜱(Boophilus microplus)试验(BOOPMI注射)
溶剂:二甲基亚砜
为制备合适的活性化合物制剂,将1重量份活性化合物与所述量的溶剂和乳化剂混合,并用含乳化剂的水将浓液稀释至所需浓度。
将活性化合物溶液注射到微小牛蜱腹中并将该动物转移到器皿中并贮存在气温调节室中。
经所需时间段之后,确定以%计的活性。100%的情况意指没有蜱虫产受精卵。
本试验中,例如,制备实施例的以下化合物在20μg/动物的施用率下显示出≥90%的活性:
I-b-10,I-b-55,I-b-70,I-c-10,I-c-22。
实施例G
临界浓度试验/土壤昆虫-转基因植物的处理
试验昆虫:diabrotica balteata-在土壤中的幼虫
溶剂:7重量份丙酮
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份活性化合物与所述量的溶剂混合,添加所述量的乳化剂,并用水将浓液稀释至所需浓度。
将活性化合物制剂浇泼在土壤上。此处,制剂中活性化合物的浓度实质上并不重要,只有每体积单位的土壤中活性化合物的重量才是重要的,其以ppm(mg/l)表示。将土装入0.251的盆中,并使其保持在20℃。
制备之后,立即将5粒栽培种YIELD GUARD(Monsanto Comp.,USA的商标名)的发芽玉米粒放入每个盆中。2天之后,将合适的试验昆虫放入经处理的土壤中。再过7天之后,通过计算出苗的玉米植株确定活性化合物的活性(1株植株=20%活性)。
实施例H
烟芽夜蛾(Heliothis virescens)试验-转基因植物的处理
溶剂:7重量份丙酮
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份活性化合物与所述量的溶剂和所述量的乳化剂混合,并用水将浓液稀释至所需浓度。
将栽培种Roundup Ready(Monsanto Comp.,USA的商标名)的大豆芽(Glycine max)通过浸入所需浓度的活性化合物制剂中进行处理,并将其在叶仍湿润的情况下接种烟草蚜虫烟芽夜蛾。
经所需时间段之后,确定昆虫的灭杀率。
Claims (15)
1.式(I)的化合物
其中
X代表甲基,
Y代表甲基,
或者
X和Y均代表乙基,
A代表甲基,
B代表氢或甲基,或者
A、B与它们所连接的碳原子一起代表饱和C5-C6环烷基,所述环烷基中任选一个环成员被氧替代并且所述环烷基任选被甲基单取代,
A和Q1一起代表C 3-C5烷二基或C3-C5烯二基,其各自任选被甲基单取代,
其任选含有以下基团之一
Q1和Q2相互独立地代表氢,
或者
X代表乙基
并且
Y代表甲基
并且
a)A、B与它们所连接的碳原子一起代表其中任选一个环成员被氧替代的饱和C5-C6环烷基,
Q1和Q2代表氢
或者
b)A和Q1一起代表C3-C5烷二基或C3-C5烯二基,其各自任选被甲基单取代,
其任选含有以下基团之一
或被一个氧原子间隔或桥接,
B和Q2相互独立地代表氢,
G代表氢(a)或代表以下基团之一
其中
L代表氧,并且
M代表氧,
R1代表C1-C6烷基、C1-C2烷氧基-C1-C2烷基,或者代表被氯单取代的C1-C4烷基,
R2代表C1-C8烷基,
R4代表任选被氯单取代的C1-C4烷氧基,
R5代表任选被氯单取代的C1-C4烷氧基,
R17a和R18a代表甲基。
2.一种制备权利要求1所要求的式(I)化合物的方法,其特征在于
(A)式(I-a)的化合物,通过式(Ⅱ)的酮羧酯进行分子内环化得到,该反应如果合适在一种稀释剂的存在下并在一种碱的存在下进行:
式中
A、B、Q1、Q2、X和Y具有权利要求1给出的含义,
式中
A、B、Q1、Q2、X和Y具有权利要求1给出的含义,并且R8代表烷基,
(B)式(I-b)的化合物
(I-b):
其中
A、B、Q1、Q2、R1、X和Y具有权利要求1给出的含义,
通过以上所示式(I-a)的化合物——其中A、B、Q1、Q2、X和Y具有权利要求1给出的含义——各自与以下物质反应得到:
(α)与式(Ⅲ)的酰基卤反应
其中
R1具有权利要求1给出的含义,并且
Hal代表卤素
或者
(β)与式(IV)的羧酸酐反应
R1-CO-O-CO-R1 (IV)
其中
R1具有权利要求1给出的含义,
该反应如果合适在一种稀释剂的存在下并且如果合适在一种酸结合剂的存在下进行;
(C)式(I-c)的化合物
(I-c):
其中
A、B、Q1、Q2、R2、M、X和Y具有权利要求1给出的含义并且L代表氧,
通过以上所示式(I-a)的化合物——其中A、B、Q1、Q2、X和Y具有权利要求1给出的含义——各自与式(V)的氯甲酸酯反应得到,该反应如果合适在一种稀释剂的存在下并且如果合适在一种酸结合剂的存在下进行:
R2-M-CO-Cl (V)
其中
R2和M具有权利要求1给出的含义;
(F)式(I-e)的化合物
其中
A、B、L、Q1、Q2、R4、R5、X和Y具有权利要求1给出的含义,
通过以上所示式(I-a)的化合物——其中A、B、Q1、Q2、X和Y具有权利要求1给出的含义——各自与式(Ⅷ)的磷化合物反应得到,该反应如果合适在一种稀释剂的存在下并且如果合适在一种酸结合剂的存在下进行:
其中
L、R4和R5具有权利要求1给出的含义,并且
Hal代表卤素。
3.一种含有有效量活性化合物结合物的组合物,该结合物含有以下组分:
(a′)至少一种式(I)的化合物,
式中
A、B、G、Q1、Q2、X和Y具有权利要求1给出的含义
和
(b′)来自以下化合物组的至少一种改进作物植物相容性的化合物:
4-二氯乙酰基-1-氧杂-4-氮杂螺[4.5]癸烷、1-二氯乙酰基-六氢-3,3,8a-三甲基吡咯并[l,2-a]嘧啶-6(2H)-酮、4-二氯乙酰基-3,4-二氢-3-甲基-2H-l,4-苯并噁嗪、5-氯喹啉-8-氧乙酸1-甲基己基酯、3-(2-氯苄基)-1-(l-甲基-1-苯基乙基)脲、α-(氰基甲氧基亚氨基)-苯基乙腈、2,4-二氯苯氧基乙酸、4-(2,4-二氯苯氧基)丁酸、1-(1-甲基-1-苯基乙基)-3-(4-甲基苯基)脲、3,6-二氯-2-甲氧基苯甲酸、S-1-甲基-1-苯基乙基哌啶-1-硫代羧酸酯、2,2-二氯-N-(2-氧代-2-(2-丙烯基氨基)乙基)-N-(2-丙烯基)乙酰胺、2,2-二氯-N,N-二-2-丙烯基乙酰胺、4,6-二氯-2-苯基嘧啶、1-(2,4-二氯苯基)-5-三氯甲基-lH-l,2,4-三唑-3-羧酸乙酯、2-氯-4-三氟甲基噻唑-5-羧酸苯甲酯、4-氯-N-(l,3-二氧戊环-2-基甲氧基)-α-三氟苯乙酮肟、3-二氯乙酰基-5-(2-呋喃基)-2,2-二甲基噁唑烷、4,5-二氢-5,5-二苯基-3-异噁唑羧酸乙酯、1-(乙氧基羰基)乙基3,6-二氯-2-甲氧基苯甲酸酯、(4-氯-o-甲苯氧基)-乙酸、2-(4-氯-o-甲苯氧基)-丙酸、1-(2,4-二氯苯基)-4,5-二氢-5-甲基-lH-吡唑-3,5-二羧酸二乙酯、2-二氯甲基-2-甲基-l,3-二氧戊环、2-丙烯基-1-氧杂-4-氮杂螺[4.5]癸-4-酸二硫代酯、1,8-萘二甲酸酐、α-(l,3-二氧戊环-2-基甲氧亚氨基)-苯基乙腈、2,2-二氯-N-(l,3-二氧戊环-2-基甲基)-N-(2-丙烯基)乙酰胺、3-二氯乙酰基-2,2-二甲基噁唑烷、3-二氯乙酰基-2,2,5-三甲基噁唑烷、4-(4-氯-o-甲苯基)-丁酸、4-(4-氯苯氧基)丁酸、二苯基甲氧基乙酸、二苯基甲氧基乙酸甲酯、二苯基甲氧基乙酸乙酯、l-(2-氯苯基)-5-苯基-lH-吡唑-3-羧酸甲酯、1-(2,4-二氯苯基)-5-甲基-lH-吡唑-3-羧酸乙酯、1-(2,4-二氯苯基)-5-异丙基-1H-吡唑-3-羧酸乙酯、1-(2,4-二氯苯基)-5-(1,1-二甲基乙基)-1H-吡唑-3-羧酸乙酯、1-(2,4-二氯苯基)-5-苯基-1H-吡唑-3-羧酸乙酯、5-(2,4-二氯苄基)-2-异噁唑啉-3-羧酸乙酯、5-苯基-2-异噁唑啉-3-羧酸乙酯、5-(4-氟苯基)-5-苯基-2-异噁唑啉-3-羧酸乙酯、1,3-二甲基丁-1-基5-氯喹啉-8-氧乙酸酯、4-烯丙氧基丁基5-氯喹啉-8-氧乙酸酯、1-烯丙氧基丙2-基5-氯喹啉-8-氧乙酸酯、5-氯喹喔啉-8-氧乙酸甲酯、5-氯喹啉-8-氧乙酸乙酯、5-氯喹喔啉-8-氧乙酸烯丙酯、2-氧代丙-1-基5-氯喹啉-8-氧乙酸酯、5-氯喹啉-8-氧丙二酸二乙酯、5-氯喹喔啉-8-氧丙二酸二烯丙酯、5-氯喹啉-8-氧丙二酸二乙酯、4-羧基苯并二氢吡喃-4-基乙酸、4-氯苯氧基乙酸、3,3'-二甲基-4-甲氧基二苯甲酮、1-溴-4-氯甲基磺酰基苯、1-[4-(N-2-甲氧基苯甲酰基氨磺酰基)苯基]-3-甲基脲、1-[4-(N-2-甲氧基苯甲酰基氨磺酰基)苯基]-3,3-二甲基脲、1-[4-(N-4,5-二甲基苯甲酰基氨磺酰基)苯基]-3-甲基脲、1-[4-(N-萘基氨磺酰基)苯基]-3,3-二甲基脲、N-(2-甲氧基-5-甲基苯甲酰基)-4-(环丙基氨基羰基)苯磺酰胺,
和/或一种通过下列通式定义的化合物:
通式(Ⅱa)
或通式(Ⅱb)
或通式(Ⅱc)
其中
m代表数值0、1、2、3、4或5,
A1代表以下所示二价杂环基团之一
n代表数值0、1、2、3、4或5,
A2代表任选被C1-C4烷基和/或C1-C4烷氧基羰基和/或C1-C4烯氧基羰基取代的具有1或2个碳原子的烷二基,
R14代表羟基、巯基、氨基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基氨基或二(C1-C4烷基)氨基,
R15代表羟基、巯基、氨基、C1-C7烷氧基、C1-C6烯氧基、C1-C6烯氧基-C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基氨基或二(C1-C4烷基)氨基,
R16代表任选被氟、氯和/或溴取代的C1-C4烷基,
R17代表氢,各自任选被氟、氯和/或溴取代的C1-C6烷基、C2-C6烯基或C2-C6炔基、C1-C4烷氧基-C1-C4烷基、二氧戊环基-C1-C4烷基、呋喃基、呋喃基-C1-C4烷基、噻吩基、噻唑基、哌啶基,或任选被氟、氯和/或溴或者C1-C4烷基取代的苯基,
R18代表氢,各自任选被氟、氯和/或溴取代的C1-C6烷基、C2-C6烯基或C2-C6炔基、C1-C4烷氧基-C1-C4烷基、二氧戊环基-C1-C4烷基、呋喃基、呋喃基-C1-C4烷基、噻吩基、噻唑基、哌啶基,或任选被氟、氯和/或溴或者C1-C4烷基取代的苯基,
R17和R18还一起代表各自任选被C1-C4烷基、苯基、呋喃基、稠合苯环取代或被两个与其所连接的C原子一起形成一个5元或6元碳环的取代基取代的C3-C6烷二基或C2-C5氧杂烷二基,
R19代表氢、氰基、卤素,或者代表各自任选被氟、氯和/或溴取代的C1-C4烷基、C3-C6环烷基或苯基,
R20代表氢,各自任选被羟基、氰基、卤素或C1-C4烷氧基取代的C1-C6烷基、C3-C6环烷基或三(C1-C4烷基)甲硅烷基,
R21代表氢、氰基、卤素,或者代表各自任选被氟、氯和/或溴取代的C1-C4烷基、C3-C6环烷基或苯基,
X1代表硝基、氰基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基,
X2代表氢、氰基、硝基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基,
X3代表氢、氰基、硝基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基,
和/或下列通式定义的化合物:
通式(Ⅱd)
或通式(Ⅱe)
其中
t代表数值0、1、2、3、4或5,
v代表数值0、1、2、3、4或5,
R22代表氢或C1-C4烷基,
R23代表氢或C1-C4烷基,
R24代表氢,各自任选被氰基、卤素或C1-C4烷氧基取代的C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基氨基或二(C1-C4烷基)氨基,或者各自任选被氰基、卤素或C1-C4烷基取代的C3-C6环烷基、C3-C6环烷基氧基、C3-C6环烷基硫基或C3-C6环烷基氨基,
R25代表氢,任选被氰基、羟基、卤素或C1-C4烷氧基取代的C1-C6烷基,各自任选被氰基或卤素取代的C3-C6烯基或C3-C6炔基,或任选被氰基、卤素或C1-C4烷基取代的C3-C6环烷基,
R26代表氢,任选被氰基、羟基、卤素或C1-C4烷氧基取代的C1-C6烷基,各自任选被氰基或卤素取代的C3-C6烯基或C3-C6炔基,任选被氰基、卤素或C1-C4烷基取代的C3-C6环烷基,或者任选被硝基、氰基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基取代的苯基,或者与R25一起代表各自任选被C1-C4烷基取代的C2-C6烷二基或C2-C5氧杂烷二基,
X4代表硝基、氰基、羧基、氨基甲酰基、甲酰基、氨磺酰基、羟基、氨基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基,并且
X5代表硝基、氰基、羧基、氨基甲酰基、甲酰基、氨磺酰基、羟基、氨基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基。
5.权利要求3和4之一所要求的组合物,其中所述改进作物植物相容性化合物为解草酯。
6.权利要求3和4之一所要求的组合物,其中所述改进作物植物相容性化合物为吡唑解草酯。
7.权利要求1所要求的式(I)化合物用于制备杀虫剂和/或除草剂的用途。
8.杀虫剂和/或除草剂,其特征在于它们含有至少一种权利要求1所要求的式(I)化合物。
9.一种防治害虫和/或不想要的植物的方法,其特征在于将权利要求1所要求的式(I)化合物作用于害虫和/或其生境。
10.权利要求1所要求的式(I)化合物用于防治害虫和/或不想要的植物的用途。
11.一种制备杀虫剂和/或除草剂的方法,其特征在于将权利要求1所要求的式(I)化合物与填充剂和/或表面活性剂混合。
12.一种防治不想要的植物的方法,其特征在于将权利要求3所要求的组合物作用于植物或其环境。
13.权利要求3所要求的组合物用于防治不想要的植物的用途。
14.一种防治不想要的植物的方法,其特征在于将权利要求1所要求的式(I)化合物和权利要求3所要求的改进作物植物相容性化合物以短的时间间隔相继分别作用于植物或其环境。
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US6515184B1 (en) | 1995-10-13 | 2003-02-04 | Bayer Aktiengesellschaft | Cyclopentane-1,3-dione derivatives, herbicidal and pesticidal compositions containing them, methods of using them to combat pests and weeds and process for the preparation thereof |
DE19621522A1 (de) | 1996-05-29 | 1997-12-04 | Hoechst Schering Agrevo Gmbh | Neue N-Acylsulfonamide, neue Mischungen aus Herbiziden und Antidots und deren Verwendung |
DE19708607A1 (de) | 1997-03-03 | 1998-09-10 | Bayer Ag | 2-Arylcyclopentan-1,3-dione |
DE19742951A1 (de) | 1997-09-29 | 1999-04-15 | Hoechst Schering Agrevo Gmbh | Acylsulfamoylbenzoesäureamide, diese enthaltende nutzpflanzenschützende Mittel und Verfahren zu ihrer Herstellung |
DE19808261A1 (de) | 1998-02-27 | 1999-10-28 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
DE19813354A1 (de) | 1998-03-26 | 1999-09-30 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
DE19818732A1 (de) | 1998-04-27 | 1999-10-28 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
DE19827855A1 (de) | 1998-06-23 | 1999-12-30 | Hoechst Schering Agrevo Gmbh | Kombinationen aus Herbiziden und Safenern |
BR0306957A (pt) | 2002-01-22 | 2004-12-14 | Syngenta Participations Ag | Herbicidas |
DE10311300A1 (de) | 2003-03-14 | 2004-09-23 | Bayer Cropscience Ag | 2,4,6-Phenylsubstituierte cyclische Ketoenole |
DE10326386A1 (de) | 2003-06-12 | 2004-12-30 | Bayer Cropscience Ag | N-Heterocyclyl-phenylsubstituierte cyclische Ketoenole |
-
2006
- 2006-01-07 DE DE102006000971A patent/DE102006000971A1/de not_active Withdrawn
-
2007
- 2007-01-03 EP EP07702572A patent/EP1976819A2/de not_active Withdrawn
- 2007-01-03 CA CA002636352A patent/CA2636352A1/en not_active Abandoned
- 2007-01-03 AR ARP070100028A patent/AR059134A1/es not_active Application Discontinuation
- 2007-01-03 BR BRPI0706419-5A patent/BRPI0706419A2/pt not_active IP Right Cessation
- 2007-01-03 US US12/159,967 patent/US8168832B2/en not_active Expired - Fee Related
- 2007-01-03 CN CN2007800078184A patent/CN101395116B/zh not_active Expired - Fee Related
- 2007-01-03 UA UAA200810185A patent/UA93229C2/ru unknown
- 2007-01-03 WO PCT/EP2007/000023 patent/WO2007080066A2/de active Application Filing
- 2007-01-03 RU RU2008131800/04A patent/RU2008131800A/ru not_active Application Discontinuation
- 2007-01-03 KR KR1020087019240A patent/KR20080094676A/ko not_active Application Discontinuation
- 2007-01-03 AU AU2007204432A patent/AU2007204432A1/en not_active Abandoned
- 2007-01-03 JP JP2008548994A patent/JP2009522331A/ja active Pending
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN1514829A (zh) * | 1999-09-07 | 2004-07-21 | �����ɷ� | 新颖的除草剂 |
CN1431996A (zh) * | 2000-04-03 | 2003-07-23 | 拜尔公司 | 作为杀虫剂和除草剂的c2-苯基取代的环状酮烯醇类化合物 |
Also Published As
Publication number | Publication date |
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AR059134A1 (es) | 2008-03-12 |
JP2009522331A (ja) | 2009-06-11 |
CN101395116A (zh) | 2009-03-25 |
BRPI0706419A2 (pt) | 2011-03-29 |
US20090137393A1 (en) | 2009-05-28 |
UA93229C2 (ru) | 2011-01-25 |
AU2007204432A1 (en) | 2007-07-19 |
CA2636352A1 (en) | 2007-07-19 |
EP1976819A2 (de) | 2008-10-08 |
WO2007080066A2 (de) | 2007-07-19 |
KR20080094676A (ko) | 2008-10-23 |
ZA200805807B (en) | 2009-10-28 |
WO2007080066A3 (de) | 2007-11-08 |
DE102006000971A1 (de) | 2007-07-12 |
US8168832B2 (en) | 2012-05-01 |
RU2008131800A (ru) | 2010-02-20 |
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