CN1187820A - 苯并咪唑衍生物 - Google Patents
苯并咪唑衍生物 Download PDFInfo
- Publication number
- CN1187820A CN1187820A CN96194690A CN96194690A CN1187820A CN 1187820 A CN1187820 A CN 1187820A CN 96194690 A CN96194690 A CN 96194690A CN 96194690 A CN96194690 A CN 96194690A CN 1187820 A CN1187820 A CN 1187820A
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- CN
- China
- Prior art keywords
- carbon atom
- alkyl
- atom
- group
- haloalkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title abstract 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 239000002253 acid Substances 0.000 claims abstract description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 239000000463 material Substances 0.000 claims abstract description 18
- 230000003641 microbiacidal effect Effects 0.000 claims abstract description 7
- 229940124561 microbicide Drugs 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 235
- 229910052799 carbon Inorganic materials 0.000 claims description 228
- -1 hydroxycarbonyl group Chemical group 0.000 claims description 107
- 125000005843 halogen group Chemical group 0.000 claims description 57
- 125000003545 alkoxy group Chemical group 0.000 claims description 49
- 229910052731 fluorine Inorganic materials 0.000 claims description 42
- 239000011737 fluorine Substances 0.000 claims description 42
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 239000000460 chlorine Substances 0.000 claims description 41
- 229910052801 chlorine Inorganic materials 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 40
- 125000001188 haloalkyl group Chemical group 0.000 claims description 36
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000000623 heterocyclic group Chemical group 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 23
- 125000004414 alkyl thio group Chemical group 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 17
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 238000006467 substitution reaction Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
- 239000011230 binding agent Substances 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 244000005700 microbiome Species 0.000 claims description 11
- 239000005864 Sulphur Substances 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000002883 imidazolyl group Chemical class 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- VEKMJKMSTPFHQD-UHFFFAOYSA-N 1h-benzimidazole-2-carbonitrile Chemical compound C1=CC=C2NC(C#N)=NC2=C1 VEKMJKMSTPFHQD-UHFFFAOYSA-N 0.000 claims description 6
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000001118 alkylidene group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000013589 supplement Substances 0.000 claims description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000004149 thio group Chemical group *S* 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004666 alkoxyiminoalkyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 3
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 239000002855 microbicide agent Substances 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005277 alkyl imino group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 2
- 230000002195 synergetic effect Effects 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 229910052751 metal Chemical class 0.000 abstract description 6
- 239000002184 metal Chemical class 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 39
- 125000001246 bromo group Chemical group Br* 0.000 description 24
- 241000894006 Bacteria Species 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 17
- 241000233866 Fungi Species 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- 239000013543 active substance Substances 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 12
- 150000003851 azoles Chemical class 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 201000010099 disease Diseases 0.000 description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 241000589516 Pseudomonas Species 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 240000006365 Vitis vinifera Species 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000002346 iodo group Chemical group I* 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 5
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 5
- 240000003768 Solanum lycopersicum Species 0.000 description 5
- 235000009754 Vitis X bourquina Nutrition 0.000 description 5
- 235000012333 Vitis X labruscana Nutrition 0.000 description 5
- 235000014787 Vitis vinifera Nutrition 0.000 description 5
- 150000001412 amines Chemical group 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 241000371644 Curvularia ravenelii Species 0.000 description 4
- 239000005946 Cypermethrin Substances 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 241000233679 Peronosporaceae Species 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 241000233622 Phytophthora infestans Species 0.000 description 4
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 241000228452 Venturia inaequalis Species 0.000 description 4
- 150000001345 alkine derivatives Chemical class 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 229960005424 cypermethrin Drugs 0.000 description 4
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 4
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 4
- 239000012770 industrial material Substances 0.000 description 4
- 239000002917 insecticide Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 3
- 241000221198 Basidiomycota Species 0.000 description 3
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 description 3
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
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- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
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- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 3
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- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- 150000002696 manganese Chemical class 0.000 description 3
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 3
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- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 3
- 150000003751 zinc Chemical class 0.000 description 3
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 2
- ATROHALUCMTWTB-WYMLVPIESA-N (z)-n-diethoxyphosphinothioyloxybenzenecarboximidoyl cyanide Chemical compound CCOP(=S)(OCC)O\N=C(/C#N)C1=CC=CC=C1 ATROHALUCMTWTB-WYMLVPIESA-N 0.000 description 2
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 2
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 2
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical class C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
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- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
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- 235000013311 vegetables Nutrition 0.000 description 1
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- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明涉及式(Ⅰ)新的苯并咪唑衍生物,其中R1、R2、X1、X2、X3、X4和Y各在说明书中进行了定义,和其酸加成盐及金属盐配合物,涉及制备这些化合物的方法,以及这些化合物作为农作物保护和材料保护中的杀微生物剂的用途。
Description
本发明涉及新的苯并咪唑衍生物,其制备方法,以及它们在农作物保护和材料保护中作为杀微生物剂的用途。
已知一些苯并咪唑衍生物具有杀真菌性质(参见DE-A4139950和EP-A0517476)。例如2-氰基-1-二甲基氨基磺酰基-6,6,7,7-四氟-[1,4]二氧杂环己烯并[2,3-f]苯并咪唑和2-氰基-6,6-二氟-1-二甲基氨基磺酰基-[1,3]间二氧杂环戊烯并[4,5-f]苯并咪唑可以用来控制真菌。这些化合物活性好,但是在一些情况下在低应用比例时遗留一些预见得到的问题。
因此,本发明提供下式新的苯并咪唑衍生物其中
X1、X2、X3和X4各自独立地代表氢、卤原子、氰基、硝基、烷基、卤代烷基、烷氧基、卤代烷氧基、烷硫基、卤代烷硫基、烷基亚磺酰基、卤代烷基亚磺酰基、烷基磺酰基、卤代烷基磺酰基、任意取代的环烷基、羟基羰基、烷基羰基、烷氧基羰基、环烷基羰基、环烷氧基羰基,
代表或-Z-R5,其中
R3和R4各自独立地代表氢、烷基、卤代烷基、烷氧基烷基、烷基羰基、任意取代的芳基、任意取代的芳基羰基、任意取代的芳基磺酰基、任意取代的芳基氨基羰基或任意取代的芳基甲基磺酰基,或者
R3和R4与和它们相连的氮原子一起代表任意被烷基取代的可以包含另外一个氧原子或一个烷基亚氨基基团的杂环,
Q代表一个直接的键或一个羰基,
R5代表任意取代的芳基或者代表任意取代的杂环基,
Z代表一个直接的键,代表CH2、O、S、SO、SO2、CO或偶氮基,或者
代表-CO-O-,其中氧原子与芳基或杂环残基键联,或者
代表-SO2-O-,其中硫原子与芳基或杂环残基键联,或者
代表-S-CH2-SO2-,其中硫基的硫原子与芳基或杂环残基键联,或者
X2和X3一起代表有3或4个原子的任意取代的亚烷基链,其中一个或两个(不相邻)碳原子可以被氧原子置换,
R6代表烷基,卤代烷基或任意被卤素和/或卤代烷基取代的苄基,
R2代表任意取代的杂环基,
Y代表一个直接的键,代表-CH2-、-CH2-CH2-、-CO-、-SO2-、-CO-O-或-SO-O-,其中在后两个基团的情况下碳原子或硫原子与咪唑环的氮原子键合,和其酸加成盐和金属盐配合物。
而且发现,如果适当地存在一种酸结合剂和如果存在一种稀释剂,则当式(II)氰基苯并咪唑其中
X1、X2、X3和X4各如上所定义,
与式(III)Hal-Y-R2的卤代物反应时,生成式(I)苯并咪唑衍生物和其酸加成盐和金属盐配合物,
其中R2和Y各如上文定义,
Hal代表氯或溴,
而且,如果适当,所得的下式苯并咪唑其中
R2、Y、X1、X2、X3和X4各如上文所定义,任选其一地
a)存在一种酸结合剂和存在一种稀释剂下与硫化氢反应,或者
b)在存在一种酸结合剂和存在一种稀释剂下,与式(IV)H-S-R6硫化合物反应,其中
R6如上文所定义,以及如果适当,向所得式(I)化合物中加入一种酸或一种金属盐。
最终,发现式(I)苯并咪唑衍生物和其酸加成盐和金属盐配合物具有非常好的杀微生物性能,可用于农作物保护和材料保护。
出人意料的是,本发明化合物具有比现有技术中的相同作用和类似结构的化合物2-氰基-1-二甲基氨基磺酰基-6,6,7,7-四氟-[1,4]二氧杂环己烯并[2,3-f]苯并咪唑和2-氰基-6,6-二氟-1-二甲基氨基磺酰基[1,3]-间二氧杂环戊烯并[4,5-f]苯并咪唑更好的杀真菌活性。
本发明化合物通式定义在式(I)中给出。其中
X1、X2、X3和X4各自独立地代表氢、氟、氯、溴、碘、氰基、硝基,有1-8个碳原子的直链或支链烷基,有1-6个碳原子和1-13个相同或不同卤原子的直链或支链卤代烷基,有1-8个碳原子的直链或支链烷氧基,有1-6个碳原子和1-13个相同或不同卤原子的直链或支链卤代烷氧基,有1-8个碳原子的直链或支链烷硫基,有1-6个碳原子和1-13个相同或不同卤原子的直链或支链卤代烷硫基,有1-8个碳原子的直链或支链烷基亚磺酰基,有1-6个碳原子和1-13个相同或不同卤原子的直链或支链卤代烷基亚磺酰基,有1-8个碳原子的直链或支链烷基磺酰基,有1-6个碳原子和1-13个相同或不同卤原子的直链或支链卤代烷基磺酰基,有3-6个碳原子的环烷基,该环烷基可有可无地被相同或不同的选自卤素和具有1-4个碳原子的烷基一元至五元取代,代表羟基羰基,在直链或支链烷基部分具有1-6个碳原子的烷基羰基,在直链或支链烷氧基部分具有1-6个碳原子的烷氧羰基,在环烷基具有3-6个碳原子的环烷基羰基,在环烷基部分具有3-6个碳原子的环烷氧基羰基,代表或-Z-R5
R3和R4优选各自独立地代表氢,具有1-6个碳原子的直链或支链烷基,具有1-6个碳原子和1-13个相同或不同卤原子的直链或支链卤代烷基,在烷氧基部分有1-4个碳原子且在烷基部分有1-4个碳原子的直链或支链烷氧基烷基,在直链或支链烷基部分具有1-6个碳原子的烷基羰基,具有6-10个碳原子的芳基,在芳基部分有6-10个碳原子的芳基羰基,具有6-10个碳原子的芳基磺酰基,芳基部分有6-10个碳原子的芳基氨基羰基,或者代表芳基部分有6-10个碳原子的芳基甲基磺酰基,上述的每一个芳基残基可以是被相同或不同的选自下列的基团一元至三元取代的:卤素、氰基、硝基,有1-4个碳原子的烷基,有1-4个碳原子的烷氧基,有1-4个碳原子的烷硫基,有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基,有1-4个碳原子和1-5个相同或不同卤原子的卤代烷氧基,具有1-4个碳原子和1-5个相同或不同卤原子的卤代烷硫基,有1-4个碳原子的烷基亚磺酰基,有1-4个碳原子的烷基磺酰基,具有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基亚磺酰基,和具有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基磺酰基,
另外,R3和R4与它们连接的氮原子一起优选代表5元或六元杂环,其可有可无地被具有1-4个碳原子的烷基一元至三元取代,并且其可以另外含有一个氧原子或一个C1-C4烷基亚氨基,
Q优选代表一个直接的键或者代表一个羰基,
R5优选代表具有6-10个碳原子的芳基,每一个这样的残基可能被相同或不同的选自下组的取代基一元至三元取代:卤素、氰基、硝基;具有1-4个碳原子的烷基,具有1-4个碳原子的烷氧基,具有1-4个碳原子的烷硫基,具有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基,具有1-4个碳原子和1-5个相同或不同卤原子的卤代烷氧基,具有1-4个碳原子和1-5个相同或不同卤原子的卤代烷硫基,具有1-4个碳原子的烷基亚磺酰基,具有1-4个碳原子的烷磺酰基,具有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基亚磺酰基,和具有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基磺酰基,或者
R5优选代表5元或6元且含有1-3个杂原子例如氮原子、氧原子和/或硫原子的饱和或不饱和杂环残基,这些残基可能是被相同或不同的下组取代基一元至三元取代的:卤素,有1-4个碳原子的烷基,有1-4个碳原子的烷氧基,有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基,有1-4个碳原子和1-5个相同或不同卤原子的卤代烷氧基,在烷氧基部分有1-3个碳原子的烷氧羰基,有3-6个碳原子的环烷基,氰基和硝基,
Z优选代表一个直接的键,也代表CH2、O、S、SO、SO2、CO或偶氮基团,或者
优选代表-CO-O-,其中氧原子与芳基或杂环残基键合,或者
优选代表-SO2-O-,其中硫原子与芳基或杂环残基键合,或者
优选代表-S-CH2-SO2-,其中硫代基团中的硫原子与芳基或杂环残基键合,
X2和X3一起也优选代表有3或4个碳原子的亚烷基,其可有可无地被卤素,有1-4个碳原子的烷基和/或1-4个碳原子和1-9个卤原子的卤代烷基一元至六元取代,其中一个或两个(不相邻)碳原子可以被氧原子置换,
R6优选代表1-4个碳原子的直链或支链烷基,有1-4个碳原子和1-9个相同或不同卤原子的直链或支链卤代烷基,或者代表苄基,苄基可有可无地被相同或不同的选自卤素和有1或2个碳原子和1-5个相同或不同卤原子的卤代烷基的取代基一元至三元取代,
R2优选代表5元或6元有1-3个杂原子例如氮原子,氧原子和/或硫原子的饱和或不饱和的,可有可无地与苯环稠合的杂环残基,这些残基可以被下组相同或不同的取代基一元至三元取代:卤素、氰基、硝基、羟基、氨基、甲酰基、羧基、氨基甲酰基、硫代氨基甲酰基,有1-4个碳原子的烷基,有1-4个碳原子的烷氧基,有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基,有1-4个碳原子和1-5个相同或不同卤原子的卤代烷氧基,烷氧基部分有1-4个碳原子的烷氧羰基,有3-6个碳原子的环烷基,有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基亚磺酰基,有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基磺酰基,有1-4个碳原子的烷基氨基,有1-4个碳原子的羟基烷基氨基,在每个烷基中有1-4个碳原子的二烷基氨基,烷基部分有1-4个碳原子的烷基羰基,烷基基团中有1-4个碳原子的烷基羰基氨基,烷基部分有1-4个碳原子的羟基亚氨基烷基,烷氧基部分有1-4个碳原子且在烷基部分有1-4个碳原子的烷氧亚氨基烷基,烷基部分有1-4个碳原子的烷基羰基氧基,以及卤代烷基中有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基羰基氧基,
这些杂环残基可以含有氧代基团,
Y优选代表一个直接的键,代表CH2、CH2-CH2、CO、SO2、-CO-O-或-SO-O-,其中在后两个基团的情况下,碳原子或硫原子与咪唑环中的氮原子键合。
X1、X2、X3和X4各自独立地特别优选地代表氢、氟、氯、溴、碘、氰基、硝基,有1-6个碳原子的直链或支链烷基,有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷基,有1-6个碳原子的直链或支链烷氧基,有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷氧基,有1-6个碳原子的直链或支链烷硫基,有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷硫基,有1-6个碳原子的直链或支链烷基亚磺酰基,有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷基亚磺酰基,有1-6个碳原子的直链或支链烷基磺酰基,有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷基磺酰基,有3-6个碳原子的环烷基,该环烷基可有可无地被下组相同或不同的取代基一元至三元取代:氟、氯、溴、甲基和乙基,代表羟基羰基,直链或支链烷基部分有1-4个碳原子的烷基羰基,在直链或支链烷氧基部分有1-4个碳原子的烷氧羰基,环烷基部分有3-6个碳原子的环烷基羰基,环烷基部分有3-6个碳原子的环烷氧羰基,代表
或-Z-R5。
R3和R4各自独立地特别优选地代表氢,有1-4个碳原子的直链或支链烷基,有1或2个碳原子和1-5个氟,氯和/或溴原子的卤代烷基,烷氧基部分有1-3个碳原子且烷基部分有1-3个碳原子的直链或支链烷氧烷基,直链或支链烷基部分有1-4个碳原子的烷基羰基,苯基,苯基羰基,苯基磺酰基,苯基氨基羰基,或苯基甲磺酰基,每一个上述苯基残基可以被下组相同或不同取代基一元至三元取代:氟、氯、溴、氰基、硝基,有1或2个碳原子的烷基,有1或2个碳原子的烷氧基,有1或2个碳原子的烷硫基,有1或2个碳原子的及1-5个氟、氯和/或溴原子的卤代烷基,有1或2个碳原子和1-5个氟、氯和/或溴原子的卤代烷氧基,有1或2个碳原子和1-5个氟、氯和/或溴原子的卤代烷硫基,有1或2个碳原子的烷基亚磺酰基,有1或2个碳原子的烷基磺酰基,有1或2个碳原子和1-5个氟、氯和/或溴原子的卤代烷基亚磺酰基,和有1或2个碳原子和1-5个氟、氯和/或溴原子的卤代烷基磺酰基。
另外,R3和R4与它们连接的氮原子一起特别优选地代表饱和的5元或6元杂环,该杂环可有可无地被甲基和/或乙基一元至三元取代,其中该环中的一个碳原子可以被氧或甲基亚氨基置换。
Q特别优选地代表一个直接的键或一个羰基。
R5特别优选地代表可以被下组相同或不同的取代基一元至三元取代的苯基:氟、氯、溴、氰基、硝基,有1或2个碳原子的烷基,有1或2个碳原子的烷氧基,有1或2个碳原子的烷硫基,有1或2个碳原子和1-5个氟、氯和/或溴原子的卤代烷基,有1或2个碳原子和1-5个氟、氯和/或溴原子的卤代烷氧基,有1或2个碳原子和1-5个氟、氯和/或溴原子的卤代烷硫基,有1或2个碳原子的烷基亚磺酰基,有1或2个碳原子的烷基磺酰基,有1或2个碳原子和1-5个氟、氯和/或溴原子的卤代烷基亚磺酰基以及有1或2个碳原子和1-5个氟、氯和/或溴原子的卤代烷基磺酰基,或者
R5特别优选地代表5元或6元有1-3个杂原子例如氮原子,氧原子和/或硫原子的饱和或不饱和杂环残基,这些残基可以被下组相同或不同的取代基一元至三元取代:氟、氯、溴,有1或2个碳原子的烷基,有1或2个碳原子的烷氧基,有1或2个碳原子以及1-5个氟、氯和/或溴原子的卤代烷基,有1或2个碳原子和1-5个氟、氯和/或溴原子的卤代烷氧基,烷氧基部分有1或2个碳原子的烷氧羰基,有3-6个碳原子的环烷基,氰基和硝基。
Z特别优选地代表一个直接的键和CH2、O、S、SO、SO2、CO或偶氮基团,或者
代表-CO-O-,其中氧原子与苯基或杂环残基键合,或者
代表-SO2-O-,其中硫原子与苯基或杂环残基键合,或者
代表-S-CH2-SO2-,其中硫代基团中的硫原子与苯基或杂环基团键合。
X2和X3另外优选地代表有3或4个碳原子的亚烷基链,其可有可无地被氟、氯、甲基和/或三氟甲基一元至六元取代,其中一个或两个(不相邻)的碳原子可以被氧原子置换。
R6特别优选地代表有1-4个碳原子的直链或支链烷基,有1-4个碳原子和1-5个氟、氯和/或溴原子的直链或支链卤代烷基,或者代表苄基,该苄基可有可无地被相同或不同的取代基氟、氯和三氟甲基一元或二元取代。
R2特别优选地代表5元或6元含有1-3个杂原子例如氮原子,氧原子和/或硫原子的饱和或不饱和的,可有可无地与苯环稠合的杂环残基,这些残基可以被下组相同或不同的取代基一元至三元取代:氟、氯、溴、氰基、硝基、羟基、氨基、甲酰基、羧基、氨基甲酰基、硫代氨基甲酰基,有1-4个碳原子的烷基,有1-4个碳原子的烷氧基,有1或2个碳原子和1-5个氟、氯和/或溴原子的卤代烷基,有1或2个碳原子和1-5个氟、氯和/或溴原子的卤代烷氧基,烷氧基部分有1或2个碳原子的烷氧羰基,有3-6个碳原子的环烷基,有1或2个碳原子和1-5个氟、氯和/或溴原子的卤代烷基亚磺酰基,有1或2个碳原子和1-5个氟、氯和/或溴原子的卤代烷基磺酰基,有1或2个碳原子的烷基氨基,有1或2个碳原子的羟基烷基氨基,各烷基中有1-2个碳原子的二烷基氨基,烷基部分有1或2个碳原子的烷基羰基,烷基部分有1-3个碳原子的烷基羰基氨基,烷基部分有1或2个碳原子的羟基亚氨基烷基,烷氧基部分有1或2个碳原子且烷基部分有1或2个碳原子的烷氧亚氨基烷基,烷基部分有1或2个碳原子的烷基羰基氧基,卤代烷基部分有1或2个碳原子和1-5个氟、氯和/或溴原子的卤代烷基羰基氧基,
这些杂环基可以含有一个或两个氧代基团。
Y特别优选地代表一个直接的键,代表CH2、CH2-CH2、CO、SO2、-CO-O-或-SO-O-,其中在后两个基团的情况下,碳原子或硫原子与咪唑的氮原子键合。
X1、X2、X3和X4各自独立地特别地优选代表氢、氟、氯、溴、氰基、硝基,代表甲基、乙基,正或异丙基,正、异、仲或叔丁基,甲氧基、乙氧基、正或异丙氧基,甲基硫基、乙基硫基,正或异丙基硫基,甲基亚磺酰基、乙基亚磺酰基,甲磺酰基、乙磺酰基、三氟甲基、二氟甲氧基、三氟甲氧基、二氟甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、乙酰基、乙酰氧基、甲氧羰基、乙氧羰基、环丙基、环己基、代表
或-Z-R5。
R3和R4各自独立地非常特别地优选地代表氢、甲基、乙基、正丙基、异丙基或苯基。
R3和R4与它们连接的氮原子一起也非常特别地优选代表吡咯烷基,哌啶基,吗啉基或4-甲基-哌嗪基。
Q非常特别地优选代表一个直接的键或者代表羰基。
R5非常特别地优选代表苯基,其可以被下组相同或不同取代基一元至三元取代:氟、氯、溴、氰基、硝基、甲基、乙基、正或异丙基、正、异、仲或叔丁基,甲氧基、乙氧基、正或异丙氧基、甲基硫基、乙基硫基、正或异丙基硫基,甲基亚磺酰基、乙基亚磺酰基,甲磺酰基,乙磺酰基,三氟甲基,二氟甲氧基,三氟甲氧基,二氟甲基硫基,三氟甲基硫基,二氟甲基亚磺酰基和三氟甲磺酰基,或者
R5非常特别地优选代表吡咯基、呋喃基、噻吩基、吡唑基、咪唑基、噻唑基、异噻唑基、噁唑基、异噁唑基、噁二唑基、噻二唑基、1,2,3-三嗪基、1,2,4-三嗪基、1,3,5-三嗪基、吡啶基、嘧啶基、吡嗪基、哒嗪基,这些残基可以被相同或不同的取代基氟、氯、甲基、甲氧基、三氟甲基、三氟甲氧基和三氟甲氧基一元至三元取代。
Z非常特别地优选代表一个直接的键,和代表CH2、O、S、SO、SO2、CO或偶氮基团,或者
代表-CO-O-,其中氧原子与苯基或杂环残基键合,或者
代表-SO2-O-,其中硫原子与苯基或杂环残基键合,或者
代表-S-CH2-SO2-,其中硫代基团中的硫原子与苯基或杂环残基键合。
X2和X3一起另外非常特别地优选代表下列基团-O-CF2-O-、-O-CF2-CHF-O-、-O-CHF-CHF-O-、-O-CF2-CF2-O-、-O-CF2-CFCl-O-、-O-CFCl-CFCl-O-、-O-CF2-CF2-或-CF2-CF2-O-。
R6非常特别地优选代表甲基、乙基、异丙基、三氯甲基、三氟甲基或苄基。
R2非常特别地优选代表吡咯基、呋喃基、噻吩基、吡唑基、咪唑基、噻唑基、异噻唑基、噁唑基、异噁唑基、噁二唑基、噻二唑基、1,2,3-三嗪基、1,2,4-三嗪基、1,3,5-三嗪基、吡啶基、嘧啶基、吡嗪基、哒嗪基、苯并呋喃基、苯并噻吩基、喹啉基或者下式残基:或
这些残基可以被相同或不同的下组取代基一元至三元取代:氟、氯、溴、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基、硫代氨基甲酰基、甲基、乙基、正或异丙基,正,异,仲或叔丁基,甲氧基,乙氧基,正或异丙氧基,甲基硫基,乙基硫基,正,或异丙基硫基,甲基亚磺酰基,乙基亚磺酰基,甲磺酰基,乙磺酰基,三氟甲基,二氟甲氧基,三氟甲氧基,二氟甲基硫基,三氟甲基硫基,三氟甲基亚磺酰基或三氟甲磺酰基,甲基氨基,乙基氨基,正或异丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,甲基羰基氨基,乙酰氧基,甲氧羰基,乙氧羰基,甲磺酰氧基,乙磺酰氧基,羟基亚氨基甲基,羟基亚氨基乙基,甲氧亚氨基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基和乙氧亚氨基乙基。
Y非常特别地优选代表一个直接的键,代表CH2、CH2-CH2、CO、SO2、-CO-O-或-SO-O-,其中在后两个基团的情况下,碳原子和硫原子与咪唑环的氮原子键合。
本发明优选化合物也是酸和那些其中R1、R2、X1、X2、X3、X4和Y各自是对于这些残基是优选的已经提及的定义的式(I)苯并咪唑衍生物的加成产物。
可以用来进行加成反应的酸优选包括氢卤酸,例如盐酸和氢溴酸,特别是盐酸,还有磷酸,硝酸,单官能和双官能羧酸和氢羧酸。例如乙酸,马来酸,琥珀酸,富马酸,酒石酸,柠檬酸,水杨酸,山梨酸和乳酸,也包括磺酸,例如对甲苯磺酸,和1,5-萘二磺酸,也包括邻磺酰苯甲酰亚胺和硫代邻磺酰苯甲酰亚胺。
本发明其它优选化合物是元素周期表主族II至IV和副族I和II以及IV至VIII金属的盐与其中R1、R2、X1、X2、X3、X4和Y各自是对于这些残基是优选的已经提及的定义的式(I)的那些苯并咪唑衍生物的加成物。
本发明中特别优选的是铜盐、锌盐、镁盐、锰盐、锡盐、铁盐和镍盐。这些盐的合适的阴离子是自能生成生理上可接受加成物的酸衍生的那些阴离子。本发明中特别优选的那种类型的酸是氢卤酸,例如盐酸和氢溴酸,还有磷酸,硝酸和硫酸。
可以提到的本发明化合物的例子是下面表中列出的苯并咪唑衍生物。表1 表1(续)表1(续)表1(续)表2 表2(续)表2(续)表2(续)表2(续)表3 表3(续)表3(续)表3(续)表3(续)表4 表4(续)表4(续)表4(续)表4(续)表5 表5(续)表5(续)表5(续)表5(续)表6 表6(续)表6(续)表6(续)表6(续)表7 表7(续)表7(续)表7(续)表7(续)表8 表8(续)表8(续)表8(续)表8(续)
如果2-氰基-6,6-二氟-3-(3,5-二甲基-异噁唑基-4-磺酰基)-[1,3]-间二氧杂环戊烯并[4,5-f]苯并咪唑用作反应起始物,并且硫化氢用作反应成分,则本发明方法可以通过下面的反应式说明:
如果2-氰基-6,6-二氟-3-(3,5-二甲基-异噁唑-4-磺酰基)-[1,3]-间二氧杂环戊烯并[4,5-f]苯并咪唑用作反应起始物,甲硫醇用作反应成分,则本发明方法可以通过下面的反应式说明:
式(II)给出了需要用作进行本发明方法第一步骤中的起始物的氰基苯并咪唑的通式定义。在该结构式中,X1、X2、X3和X4各自具有已经提及的与说明本发明式(I)化合物这些基团相关的那些定义。
式(II)氰基苯并咪唑类是已知的,或者可以根据原理上已知的方法制备(参见DE-A4139950、FR-A2572412、EP-A0181826、EP-A0517476、EP-A0549943和EP-A0487286)。
式(III)给出了进行本发明方法第一步骤也需要用作起始物的卤化物的通式定义。在该结构式中,R2和Y各自具有已经提及的与说明本发明式(I)化合物这些基团相关的那些定义。Hal代表氯和溴。
式(III)卤化物是已知的,或者可以根据已知方法制备。
进行本发明方法第一步骤的合适的稀释剂是所有商购的惰性有机溶剂。优选使用脂肪烃,环脂肪烃,芳烃,可有可无地被卤化的烃,例如汽油、苯、甲苯、二甲苯、氯苯、二氯苯、石油醚、己烷、环己烷、二氯甲烷、氯仿或四氯化碳;还有醚类,如乙醚、丙醚、二噁烷、四氢呋喃或乙二醇二甲醚或乙二醇二乙醚;还有酮类,例如丙酮或丁酮,或甲基异丁基酮;腈类,例如乙腈,丙腈或苄腈;或者酯类,例如乙酸甲酯或乙酸乙酯。
本发明方法第一步骤优选在酸结合剂存在下进行。合适的酸结合剂是所有的商售无机或者有机碱。优选使用碱土金属或碱金属氢氧化物,例如氢氧化钠、氢氧化钙、氢氧化钾、或者还有氢氧化铝,碱金属碳酸盐,例如碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠、碱金属或碱土金属乙酸盐,例如乙酸钠、乙酸钾、乙酸钙和季铵,例如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、吡啶、N-甲基哌啶、N,N-二甲基氨基吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DBN)或二氮杂双环十一碳烯(DBU)。
在进行本发明方法第一步骤时,反应温度可以在相当宽的范围内变化。一般情况下,反应在0和150℃之间,优选在20和120℃之间的温度下进行。
本发明方法第一和第二步骤一般在大气压下进行,但也可在加压或减压条件下进行。
进行本发明方法第一步骤时,一般情况下对于稀释剂中每摩尔式(II)氰基苯并咪唑使用1.0至2.0mol,优选1.0至1.3mol式(III)卤化物,以及可有可无的1.0至2.0mol,优选1.0至1.3mol酸结合剂。进行反应,后处理以及分离反应产物都使用的是已知方法(也可以参见制备实施例)。
进行本发明方法第二步骤(变通方法a)时,优选的酸结合剂是季胺,例如三乙胺。
当进行本发明方法第二步骤(变通方法a)时,合适的稀释剂是所有惰性极性有机溶剂。优选使用酰胺,例如二甲基甲酰胺,还有醚类,例如乙醚或者四氢呋喃,以及芳香胺类,例如吡啶。
当进行本发明方法第二步骤(变通方法a)时,反应温度也可以在相当宽的范围内变化。一般情况下,该步骤在-20℃和+150℃之间的温度,优选在-10℃和+80℃之间的温度下进行。
当进行本发明方法第二步骤(变通方法a)时,对于每1mol式(I-a)苯并咪唑衍生物使用过量的优选2至5mol硫化氢。用常规方法进行后处理。
式(IV)给出了需要用作进行本发明方法第二步骤(变通方法b)的反应成分的硫化合物的通式定义。在该结构式中,R6具有已经提及的与说明本发明式(I)化合物这些基团相关的那些定义。
当进行本发明方法第二步骤(变通方法b)时,优选的酸结合剂是碱金属碳酸盐,例如碳酸钠或碳酸钾。
进行本发明方法第二步骤(变通方法b)的合适的稀释剂是所有商售极性质子惰性溶剂,优选使用腈类,例如乙腈。
在进行本发明方法第二步骤(变通方法b)时,反应温度也可以在相当宽的范围内变化。一般情况下,该步骤在-20℃和+150℃,优选在-10℃和+80℃之间的温度下进行。
当进行本发明方法第二步骤(变通方法b)时,对于每1mol式(I-a)苯并咪唑衍生物,使用过量、优选2至5mol式(IV)硫化合物。用常规方法进行后处理。
式(I)苯并咪唑衍生物可以转化成酸加成盐或金属盐配合物。
制备式(I)化合物酸加成盐的合适的酸优选是那些已经提及的与说明本发明优选的酸加成盐相关的酸。
式(I)化合物酸加成盐可以用常规盐生成方法的一种简单方式获得,例如通过将一种式(I)化合物溶解于合适的惰性溶剂中并加入酸,例如盐酸,可以用已知方法分离盐,例如,通过过滤,以及如果需要,用惰性有机溶剂洗涤纯化。
用于制备本发明式(I)化合物金属盐配合物的合适的盐优选是那些已经提及的与说明本发明优选的金属盐配合物相关的金属盐的那些金属。
式(I)化合物金属盐配合物可以通过常规方法中的一种简单方法而获得,例如通过将金属盐溶解于醇,例如乙醇中,并将该溶液加入到式(I)化合物中。金属盐配合物可以用已知方法分离,例如通过过滤,以及如果需要,通过重结晶纯化。
本发明活性化合物具有强的杀微生物活性,可以用来控制不期望的微生物,例如真菌和细菌,用于农作物保护和材料保护。
不期望的微生物包括真菌,例如根肿菌真菌(Plasmodiophoromycetes),接合孢子真菌(Oomycetes),壶菌真菌(Chytridiomycetes),接合菌亚纲(Zygomycetes),子囊菌纲(Ascomycetes),担子菌纲(Basidiomycetes),半知菌纲(Deuteromycetes),以及细菌,例如假单孢菌科(Pseudomonadaceae),根瘤菌科(Rhizobiaceae),肠杆菌科(Enterobacteriaceae),棒状杆菌科(Corynebacteriaceae)和链霉菌科(Streptomycetaceae)。
一些上述种属名下的引起真菌或细菌病害的生物体作为例子可以提到下面的生物体,但不限于此:
黄单孢菌属,例如稻黄单孢菌属(Xanthomonas oryzae);
假单孢菌属,例如黄瓜角斑病假单孢菌(Pseudomonas lachrymans);
欧文氏杆菌属,例如解淀粉欧文氏杆菌(Erwinia amylovora);
腐霉属,例如终极腐霉(Pythium ultimum );
疫霉属,例如蔓延疫霉(Phytophthora infestans);
假霜霉属,例如葎草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(Pseudoperonospora cubensis);
单轴霉属,例如葡萄生单轴霉(Plasmopara viticola);
霜霉属,例如豌豆霜霉(Peronospora pisi)或芸苔霜霉(P.brassicae);
白粉菌属,例如禾白粉菌(Erysiphe graminis);
单丝壳菌属,例如苍耳单丝壳菌(Sphaerotheca fuliginea);
柄球菌属,例如苹果白粉病柄球菌(Podosphaera leucotricha);
黑星菌属,例如苹果黑星菌(Venturia inaequalis);
核腔菌属,例如圆核腔菌(Pyrenophora teres)或麦类核腔菌(P.graminea)(分生孢子形式:长蠕孢(Drechslera),同义词:长蠕孢属(Helminthosporium));
旋孢霉属,例如禾旋孢霉(Cochliobolus sativus(分生孢子形式:长蠕孢(Drechslera),同义词:长蠕孢属(Helminthosporium));
单孢锈菌属,例如疣顶单胞锈菌(Uromyces appendiculatus);
柄锈菌属,例如隐匿柄锈菌(Puccinia recondita);
腥黑粉菌属,例如小麦网腥黑粉菌(Tilletia caries);
黑粉菌属,例如裸黑粉菌(Ustilago nuda)或燕麦黑粉菌(Ustilagoavenae);
薄膜革菌属,例如佐佐木氏薄膜革菌(Pellicularia sasakii);
Pyricularia属,例如Pyricularia oryzae;
镰孢属,例如大刀镰孢(Fusarium culmorum);
葡萄孢属,例如灰色葡萄孢(Botrytis cinerea);
壳针孢属,例如颖枯壳针孢(Septoria nodorum);
小球腔菌属,例如颖枯小球腔菌(Leptosphaeria nodorum);
尾孢属,例如Cercospora canescens;
链格孢属,例如甘蓝黑斑链格孢(Alternaria brassicae);和
假尾孢属,例如Pseudocercosporella herpotrichoides。
植物对于控制植物病害所需的活性化合物之好的耐受性使可以处理植物的地上部分,无性繁殖原种和种子,以及处理土壤。
本发明活性化合物特别适于控制水果和蔬菜长期病害,例如抗黑星菌属,或者控制谷病害,例如白粉菌属,旋孢霉属,核腔菌属,或者壳针孢属,或者控制稻病害,例如抗引起稻瘟病(Pyricularia oryzae)的微生物。
在材料保护方面,本发明化合物可有来保护工业材料不受不期望微生物的侵害和破坏。
在本发明中术语工业材料指已经制得的在工业上使用的无生命材料。可以用新活性物质保护不受微生物侵害或破坏的工业材料的例子有粘合剂,胶水,纸张和纸板,纺织品,皮革,木材,涂料组合物和塑料制品,冷却润滑剂和其它能被微生物侵袭或分解的材料。要被保护的材料的范围也包括生产工厂,例如冷却循环水,其可能会被微生物的再生而不利地受影响。本发明范围中的优选的工业材料是粘合剂,胶水,纸张和纸板,皮革,木材,涂料组合物,冷却润滑剂,和热转移液体,特别是木材。
能使工业材料降解或改变的微生物的例子是细菌,真菌,酵母,藻类和粘液微生物。本发明活性物质优选作用于真菌,特别是霉菌,使木材变色和破坏木材的真菌(担子菌纲),也抗粘液生物体和藻类。
作为例子,可以提到下面微生物:
链格孢属,例如纤细链格孢(Alternaria tenuis);
曲霉属,例如黑色曲霉(Aspergillus niger);
毛壳霉属,例如球毛壳霉(Chaetomium globosum);
粉孢革菌属,例如单纯粉孢革菌(Coniophora puetana);
香茹属,例如Lentinus tigrinus;
青霉属,例如灰绿青霉(Penicillium glaucum);
多孔菌属,例如变色多孔菌(Polyporus versicolor);
短杆霉属,例如出芽短柄霉(Aureobasidium pullulans);
Sclerophoma,例如Sclerophoma pityophila;
木霉属,例如绿色木霉(Trichoderma viride);
埃希氏杆菌属,例如大肠埃希氏杆菌(Escherichia coli);
假单孢菌属,例如铜绿假单孢菌(Pesudomonas aeruginosa);
葡萄球菌属,例如金黄色葡萄球菌(Staphylococcus aureus)。
另外,本发明化合物适于控制动物害虫,优选控制节肢动物和线虫,特别是农业,林业,贮存货物和材料的保护,以及卫生领域所遇到的昆虫和蛛形纲。它们对一般敏感性和抗性的物种有效,而且在所有或某些害虫生长期有效。
式(II)氰基苯并咪唑类也具有杀真菌活性。
根据其各自的物理和/或化学性质,本发明活性物质可以转化成商售制剂,例如溶液,乳剂,悬浮液,粉剂,泡沫剂,细粉剂,颗粒剂,气溶胶,用于种子的聚合物质和包衣组合物中的特细胶囊,还有ULV冷雾剂和热雾剂。
用已知方法制备这些制剂,例如通过将活性化合物与补充剂混合,补充剂例如液体溶剂,加压的液态气体,和/或固体载体,可有可无地使用表面活性剂,如乳化剂和/或分散剂,和/或发泡剂。在使用水作为补充剂的情况下,有机溶剂例如醇也可以例如用作辅助溶剂。作为液体溶剂,合适的主要有:芳香化合物,例如二甲苯、甲苯或烷基萘,氯化的芳烃或氯化的脂肪烃,例如氯苯,二氯乙烷或二氯甲烷,脂肪烃,例如环己烷或烷烃,例如矿物油级分,醇,例如丁醇或乙二醇以及它们的醚或酯,酮,例如丙酮,甲基乙基酮,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亚砜,以及水;液态气体补充剂或载体是指常温常压下是气体的液体,例如气溶胶抛射剂,例如卤化的烃,例如丁烷,丙烷,氮和二氧化碳;作为固体载体,合适的有:例如,研细的天然矿物,例如高岭土,粘土,滑石,白垩,石英,白土(attapulgite),蒙脱石,或硅藻土,和研细的合成矿物,研细的分散的硅石,氧化铝和硅酸盐;用为颗粒剂的固体载体合适的有:例如粉碎的和分级的天然原料如方解石,大理石,浮石,海泡石,和白云石,以及合成的无机和有机粉的颗粒,和有机材料如木屑,椰子壳,玉米穗轴和烟草蒂细粒;作为乳化和/或发泡剂合适的有:例如阴离子和阳离子乳化剂,例如聚氧乙烯脂肪酸酯,聚氧乙烯脂肪醇醚,例如烷基芳基聚乙二醇醚,磺酸烷基酯,硫酸烷基酯,磺酸芳基酯,以及蛋白质水解产物;作为分散剂合适的有:例如木素亚硫酸废液和甲基纤维素。
粘合剂例如羧甲基纤维素和天然和合成的粉末,颗粒或胶乳形式的聚合物例如阿拉伯树胶,聚乙烯醇,聚乙酸乙烯酯,以及天然的磷脂例如脑磷脂和卵磷脂,和合成的磷脂可以在制剂中使用。其它添加剂可以是矿物油和植物油。
可以使用染色剂例如无机染料如氧化铁,氧化钛和普鲁士蓝,和有机染料,例如茜素染料,偶氮染料和金属酞菁染料和痕量成分例如铁盐,锰盐,硼盐,铜盐,钴盐,钼盐和锌盐。
制剂通常含有0.1~95%重量之间的活性化合物,优选0.5~90%之间。
当在农作物保护中使用本发明活性化合物时,可以和已知的杀真菌剂,杀细菌剂,杀螨剂,杀线虫剂或杀昆虫剂混合在制剂中使用,以此来扩大作用范围或者防止建立起抗性。
用于混合物的合适的成分是例如下面的物质:杀真菌剂:
2-氨基丁烷;2-苯胺基-4-甲基-6-环丙基-嘧啶;2',6'-二溴-2-甲基-4'-三氟甲氧基-4'-三氟-甲基-1,3-噻唑-5-甲酰苯胺;2,6-二氯-N-(4-三氟甲基苄基)苯甲酰胺;(E)-2-甲氧亚氨基-N-甲基-2-(2-苯氧基苯基)-乙酰胺;8-羟基喹啉硫酸盐;(E)-2-{2-[6-(2-氰基苯氧基)-嘧啶-4-基氧]-苯基}-3-甲氧基丙烯酸甲酯;(E)-甲氧亚氨基〔2-(对-甲苯基氧)-对-甲苯基〕乙酸乙酯;2-苯基苯酚(OPP),aldimorph,氨丙磷酸,敌菌灵,戊环唑,苯霜灵,邻碘酰苯胺,苯菌灵,乐杀螨,联苯,双苯三唑醇,灭瘟素,糠菌唑,乙嘧酚磺酸酯,丁赛特,
多硫化钙,敌菌丹,克菌丹,多菌灵,萎锈灵,灭螨猛,地茂散,氯化苦,百菌清,乙菌利,代森盐,霜尿氰,环唑醇,酯菌胺,
双氯酚,苄氯三唑醇,diclofluanid,哒菌清,氯硝胺,乙霉威,噁醚唑,二甲嘧酚,烯酰吗啉,烯唑醇,二硝巴豆酸酯,二苯胺,吡菌硫,灭菌磷,二噻农,多果定,联氨噁唑酮,克瘟散,epoxyconazole,乙嘧酚,土菌灵,氯苯嘧啶醇,fenbuconazole,甲呋酰苯胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,三苯基醋酸锡,三苯基氢氧化锡,福美铁,嘧菌腙,氟啶胺,fludioxonil,氟氯蓖核利,fluquinconazole,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,四氯苯酞,麦穗宁,呋霜灵,拌种胺,谷种定,六氯苯,己唑醇,噁霉灵,抑霉唑,酰胺唑,双胍辛醋酸盐,异稻瘟净,异菌脲,稻瘟灵,春雷霉素,铜制剂,例如氢氧化铜,环烷酸铜,氯化氧铜,硫酸铜,氧化铜,8-羟基喹啉铜和Bordeaux混合物,代森锰铜,代森锰锌,代森锰,嘧菌胺,灭锈胺,甲霜灵,metconazole,磺菌威,呋菌胺,代森联,噻菌胺,腈菌唑,二甲基二硫氨基甲酸镍,间硝酞异丙酯,氟苯嘧啶醇,甲呋酰胺,噁霜灵,oxamocarb,氧化萎锈灵,稻瘟酯,戊菌唑,戊菌隆,稻病磷,多马霉素,病花灵,多氧霉素,烯丙异噻唑,味鲜安,腐霉利,丙酰胺,环丙唑,丙森锌,吡嘧磷,啶斑肟,pyrimethanil,咯喹酮,五氯硝基苯(PCNB),硫和硫制剂,戊唑醇,叶枯酞,甲氯硝基苯,氟醚唑,噻菌灵,噻菌腈,硫菌灵,福美双,甲基立枯磷,甲苯氟磺胺,三唑酮,三唑醇,唑菌嗪,杨菌胺,三环唑,十三吗啉,氟菌唑,嗪氨灵,triticonazole,稻纹散,乙烯菌核利,代森锌,福美锌。杀菌剂
bronopol,双氯酚,氯甲基吡啶,二甲基二硫氨基甲酸镍,春雷霉素,异噻菌酮,furanecarboxylic,oxytetracyclin,烯丙异噻唑,链霉素,叶枯酞,硫酸铜和其它铜制剂。杀虫剂/杀螨剂/杀线虫剂
齐墩螨素,AC303630,乙酰甲胺磷,氟酯菊酯,棉铃威,涕灭威,甲体氯氰菊酯,双虫脒,avermectin,AZ60541,azadirachtin,azinphosA,azinphosM,三唑锡,苏云金杆菌,噁虫威,丙硫克百威,杀虫磺,氟氯氰菊酯,氟氯菊酯,仲丁威,brofenprox,bromophos A,合杀威,噻嗪酮,丁酮威,butylpyridaben,硫线磷,甲萘威,克百威,三硫磷,丁硫百克威,杀螟丹,CGA157419,CGA184699,chloethocarb,chlorethoxyfos,毒虫畏,定虫隆,氯甲硫磷,chlorpyrifosM,cis-resmethrin,clocythrin,四螨嗪,杀螟腈,氟氯氰菊酯,cyhalothyin,三环锡,氯氰菊酯,灭蝇胺,溴氰菊酯,demeton-M,内吸磷,杀螨隆,甲基内吸磷,二嗪磷,酚线磷,敌敌畏,clicliphos,百治磷,乙硫磷,除虫尿,乐果,甲基毒虫畏,敌噁磷,克瘟散,emamectin,高氰戊菊酯,乙硫苯威,乙硫磷,醚菊酯,灭线磷,乙嘧硫磷,虫胺磷,喹螨醚,苯丁锡,杀螟硫磷,仲丁威,苯硫威,双氧威,甲氰菊酯,fenpyrad,唑螨酯,倍硫磷,氰戊菊酯,fipronil,氟啶胺,氟螨脲,氟氰戊菊酯,氟虫脲,flufenprox,氟胺氰菊酯,地虫硫磷,安果,噻唑磷,fubfenprox,呋线威,林丹,庚烯磷,氟铃脲,噻螨酮,吡虫啉,异稻瘟净,氯唑磷,异丙氨磷,叶蝉散,噁唑磷,ivemectin,氯氟氰菊酯,lufenuron,马拉硫磷,灭蚜蜱,mevinphos,mesulfenfos,蜗牛敌,虫螨畏,甲胺磷,杀扑磷,灭梭威,灭多威,速灭威,milbemectin,久效磷,moxidectin,二溴磷 NC184,NI25,nitenpyram,杀线威,oxyclemethon M,异砜磷,parathion A,parathion M,氯菊酯,稻丰散,甲拌磷,伏杀硫磷,亚胺硫磷,磷胺,辛硫磷,抗蚜威,pirimiphos M,pirimiphos A,丙溴磷,猛杀威,丙虫磷,残杀威,丙硫磷,发果,pymetrozin,pyrichlophos,哒嗪硫磷,pyresmethrin,除虫菊酯,哒螨酮,pyrimiclifen,蚊蝇醚,喹硫磷,RH5992,蔬果磷,sebufos,silafluofen,治螟磷,甲丙硫磷,tebufenozid,tebufenpyrad,tebupirimiphos,伏虫隆,七氟菊酯,双硫磷,特灭威,特丁磷,杀虫畏,thiafenox,硫双威,久效威,thiomethon,虫线磷,thuringiensin,四溴菊酯,苯塞螨,三唑磷,triazuron,敌百虫,杀虫隆,混灭威,蚜灭多,灭除威,灭杀威,zetamethrin。
也可以是和其它已知活性化合物,例如除草剂,或者与化肥和生长调节剂的混合物。
活性化合物可以直接使用,或者以其制剂形式使用,或者从中制备使用形式,例如直接使用型溶液,悬浮液,可湿性粉末,糊剂,可溶性粉末,细粉剂和颗粒剂。其以常规方法使用,例如通过浇灌,喷施,喷雾撒拨,喷粉,喷泡沫,轻轻刷上等等。而且可以通过超低体积方法或者将活性化合物制剂或活性化合物自身注入土壤来施用活性化合物。也可以处理植物的种子。
在处理植物部分中,使用形式中的活性物质的浓度可以在相当大的范围内变化:一般在1和0.0001%重量之间,优选在0.5和0.001%重量之间。
在处理种子时,活性物质的量一般是每千克种子0.001至50g,优选0.01至10g。
处理土壤的情况下,作用地点需要活性物质的浓度为0.00001至0.1%重量,优选0.0001至0.02%重量。
用于保护工业材料的组合物含有通常1至95%,优选10至75%量的活性物质。
施用新的活性物质的浓度取决于要被处理的微生物的本质和发生情况,取决于要被保护的材料的组成。使用的最佳量可以通过试验系列方法而确定。一般情况下,使用的浓度在0.001至5%重量,优选0.05至1.0%重量范围内,以要保护的材料重量计。
本发明要在材料保护中使用的活性物质,组合物,乳油,或者通常情况下可以从中制备的制剂的作用的效力和范围,如果需要,可以通过加入其它的抗微生物活性物质,杀真菌剂,杀细菌剂,除草剂,杀昆虫剂或者其它活性物质来提高或增大,来扩大作用范围或者达到特殊效果,例如附加的抗昆虫的保护作用。这些组合物可以具有比本发明化合物更广谱的作用。
在很多情况下会产生协同效果,即混合物的活性范围比各成分的活性要优越。特别有益的混合配对物是例如下面的化合物:
亚磺酰胺类,例如苯氟磺胺(Euparene),甲苯氟磺胺(Methyleuparene),灭菌丹,fluorfolpet;
苯并咪唑类,例如多菌灵,苯菌灵,噻菌灵或者它们的盐;
硫氰酸类,例如氰硫基甲基硫代苯并咪唑(TCMTB),亚甲基二硫氰酸(MBT);
季铵化合物,例如苄基-二甲基十四烷基-铵氯化物,苄基-二甲基-十二烷基-铵氯化物,十二烷基-二甲基-铵氯化物;
吗啉衍生物,例如C11-C14-4-烷基-2,6-二甲基吗啉类似物(十二吗啉),(±)-顺-4-〔叔丁基苯基〕-2-甲基丙基〕-2,6-二甲基吗啉(丁苯吗啉),Falimorph;
酚类,例如邻-苯基苯酚,三溴苯酚,四氯苯酚,五氯苯酚,3-甲基-4-氯代苯酚,二氯苯,氯苯,或者它们的盐。
唑类,例如三唑酮,三唑醇,双苯三唑醇,戊唑醇,环丙唑,戊环唑,己唑醇,咪鲜安,环唑醇、1-(2-氯苯基)-2-(1-氯代环丙基)-3-(1,2,4-三唑-1-基)-丙-乙醇或者1-(2-氯代苯基)-2-(1,2,4-三唑-1-基-甲基)-3,3-二甲基-丁-2醇。
碘化丙炔衍生物,例如丁基氨基甲酸碘代炔丙酯(IPBL),碘代炔丙基氯代苯基缩甲醛,苯基氨基甲酸碘代炔丙酯,己基氨基甲酸碘代炔丙酯,环己基氨基甲酸碘代炔丙酯,苯基氨基甲酸碘代炔丙基氧乙酯;
碘衍生物,例如二碘代甲基-对-芳基砜,例如二碘代甲基-对-甲苯基砜;
溴衍生物,例如溴硝醇;
异噻唑啉类,例如N-甲基异噻唑啉-3-酮、5-氯-N-甲基异噻唑啉-3-酮、4,5-二氯-N-辛基异噻唑啉-3-酮、N-辛基异噻唑啉-3-酮(异噻菌酮);
苯并异噻唑啉酮类,环戊烯异噻唑啉类;
吡啶类,例如1-羟基-2-吡啶硫酮(及其钠盐,铁盐,锰盐和锌盐),四氯-4-甲基磺酰基吡啶;
金属皂类,例如锡,铜和锌的环烷酸盐,octoactes、2-乙基己酸盐,磷酸盐和苯甲酸盐,氧化物,例如TBTO、Cu2O、CuO、ZnO;
有机锡化合物,例如三丁基锡环烷酸盐和三丁基锡氧化物;
二硫代氨基甲酸二烷基酯,例如二硫代氨基甲酸二烷基酯的钠盐和锌盐,四甲基二硫化秋兰姆(TMTD);
腈类,例如2,4,5,6-四氯间苯二腈(百菌清),和其它有卤代基团的杀微生物剂,例如Cl-Ac、MCA、tectamer、溴硝醇、bromidox;
苯并噻唑类,例如2-巯基苯并噻唑;参见上文的棉隆;
喹啉类,例如8-羟基喹啉;
释放甲醛的化合物,例如苯甲醇单(多)半缩甲醛、噁唑烷类,六氢-S-三嗪类、N-羟甲基氯代乙酰胺;
反-N-(环己基二氮烯鎓二氧)铝、N-(环己基二氮烯鎓二氧)-三丁基锡或钾盐,双(N-环己基)二嗪鎓-(二氧铜或铝)。
优选使用下面的杀昆虫剂:
磷酸酯类,例如益棉磷、保棉磷、1-(4-氯苯基)-4-(O-乙基,S-丙基)磷酰氧基吡唑(TIA-230)(吡唑硫磷),毒死蜱、蝇毒磷、内吸磷、甲基内吸磷、二嗪磷、敌敌畏、乐果、灭线磷、乙嘧硫磷、杀蝗硫磷、fention、庚烯磷、对硫磷、甲基对硫磷、伏杀硫磷、辛硫磷、嘧啶磷、甲基嘧啶磷、丙溴磷、丙硫磷、甲丙硫磷、三唑磷、敌百虫;
氨基甲酸类,例如涕灭威、噁虫威、仲丁威(2-(1-甲基丙基)苯基甲基氨基甲酸酯)、丁酮威、丁酮氧威、甲萘威、克百威、丁硫百克威、除线威、叶蝉散、灭多威、杀线威、抗蚜威、猛杀威、残杀威、硫双威;
拟除虫菊酯类,例如丙烯除虫菊酯、甲体氯氰菊酯、生物苄呋菊酯、byfenthrin(FMC54800)、乙氰菊酯、氟氯氰菊酯、溴氰菊酯、cyhalothrin、氯氰菊酯、溴氰菊酯、环丙烷羧酸α-氰基-3-苯基-2-甲基苄基-2,2-二甲基-3-(2-氯代-2-三氟甲基乙烯基)酯、甲氰菊酯、五氟苯菊酯、氰戊菊酯、氟氰戊菊酯、氟氯苯菊酯、氟胺氰菊酯、氯菊酯、苄呋菊酯;硝基亚氨和硝基亚甲基化合物,例如1-〔(6-氯-3-吡啶基)-甲基〕-4,5-二氢-N-硝基-1H-咪唑-2-胺(吡虫啉)。
有机硅化合物,优选二甲基(苯基)甲硅烷基甲基3-苯氧基苯甲基醚,例如二甲基-(4-乙氧基苯基)-甲硅烷基甲基3-苯氧基苯甲基醚,或二甲基(苯基)-甲硅烷基甲基2-苯氧基-6-吡啶基甲基醚,例如二甲基(9-乙氧基苯基)-甲硅烷基甲基2-苯氧基-6-吡啶基甲基醚,或者苯基〔3-(3-苯氧基苯基)丙基〕(二甲基)-甲硅烷基,例如(4-乙氧基苯基)-〔3(4-氟-3-苯氧基苯基)-丙基〕二甲基甲硅烷基。
其它合适的活性化合物是杀藻剂,杀软体动物剂,和例如定居在船底部涂料中的海洋动物杀伤活性化合物。
通过下面的实施例详细说明本发明活性化合物的制备和应用。制备实施例实施例1
室温下,3.4g(15mmol)2-氰基-6,6-二氟-〔1,3〕间二氧杂环戊烯并[4,5-f]苯并咪唑和80ml无水四氢呋喃的混合物搅拌下与0.45g(15mmol)氰化钠(80%纯)混合,然后在室温下搅拌10分钟。之后加入2.9g(15mmol)3,5-二甲基异噁唑-4-磺酰氯,并在60℃下将混合物搅拌18个小时。终止反应,将反应混合物倒入200ml水中。每次用80ml二氯甲烷将所得混合物萃取三次。合并的有机相用硫酸钠干燥并减压浓缩。残余物在硅胶上层析,用乙醚作洗脱剂。用该方法得到1.4g(理论产率24%)2-氰基-6,6-二氟-3-(3,5-二甲基-异噁唑基-4-磺酰基)-〔1,3〕间二氧杂环戊烯〔4,5-f〕苯并咪唑,黄色固体,熔点166至170℃。实施例2
室温下,将0.30g(10mmol)氰化钠(80%纯)和40ml无水四氢呋喃的混合物在搅拌下与2.7g(10mmol)2-氰基-6,6,7,7-四氟〔1,4〕-对二氧杂环己烯并[2,3-f]苯并咪唑混合后在室温下搅拌10分钟。然后加入2.9g(15mmol)3,5-二甲基异噁唑基-4-磺酰氯,混合物在60℃搅拌4小时。终止反应,将反应混合物倒入200ml水中。每次用80ml二氯甲烷将所得混合物萃取三次。合并的有机相用硫酸钠干燥并减压浓缩。残余物在由等量乙醚和石油醚组成的20ml混合物中重结晶。用该方法得到1.9g(44%理论产率)2-氰基-6,6,7,7-四氟-3-(3,5-二甲基-异噁唑基-4-磺酰基)-〔1,4〕-对二氧杂环己烯并[2,3-f]苯并咪唑,固体,熔点100至185℃。实施例3
室温下,将0.30g(10mmol)氰化钠(80%纯)和40ml无水四氢呋喃的混合物在搅拌下与2.7g(10mmol)2-氰基-6,6,7,7-四氟〔1,4〕-对二氧杂环己烯并[2,3-f]苯并咪唑混合物室温搅拌10分钟。然后加入2.2g(12mmol)噻吩-2-磺酰氯,混合物在60℃搅拌18小时。终止反应后将反应混合物倒入200ml水中,过滤出得到的沉淀并溶解于50ml乙酸乙酯中。溶液用硫酸钠干燥后减压浓缩。残余物与20ml石油醚一起搅拌。过滤出得到的沉淀并干燥。用这种方法得到1.9g(49%理论产率)2-氰基-6,6,7,7-四氟-3-(噻吩基-2-磺酰基)-〔1,4〕-对二氧杂环己烯并[2,3-f]苯并咪唑,黄色固体,熔点180至184℃。
应用上述方法也制备了表9中列出的式(I)化合物。Using the abovementioned methods,the compounds of the formulalisted in Table 9 were also prepared.表9表9(续)表9(续)表9(续)表9(续)应用实施例
2-氰基-6,6-二氟-1-二甲基氨基磺酰基-〔1,3〕间二氧杂环戊烯并[4,5-f]苯并咪唑(来自EP-A0517476和DE-A4139950的已知化合物)。实施例A
黑星菌试验(Venturia test)(苹果)/保护
溶剂:4.7份重量的丙酮
乳化剂:0.3份重量的烷基芳基聚乙二醇醚
为了生产活性化合物的合适的制剂,将1份重量的活性化合物与上述量的溶剂和乳化剂混合,并用水将乳油稀释至所需浓度。
为试验保护活性,用活性化合物的制剂对小植物喷雾至液珠滴落。喷雾层风干后用致病微生物苹果黑星菌(Venturia inaequalis)的分生孢子的水悬浮液对植物接种,然后在20℃和100%相对空气湿度下在保温中保持1天。
然后将植物置于20℃且相对空气湿度大约为70%的温室中。
接种12天后进行评估。0%意思是相当于对照物的效力,100%表示没有发现侵害。
在该项试验中,实施例1至3的化合物在喷液中活性化合物浓度为10ppm时显示出大于50%的效力,而对比化合物(A)显示出43%的效力,对比化合物(B)显示出没有活性。
疫霉试验(番茄)/保护
溶剂:4.7份重量的丙酮
乳化剂:0.3份重量的烷基-芳基聚乙二醇醚
为生产活性化合物的合适的制剂,将1份重量的活性化合物与上述量的溶剂和乳化剂混合,并用水将乳油稀释到所需浓度。
为试验保护活性,用活性化合物的制剂对小植物喷雾至液珠滴落。喷雾层风干后,用蔓延疫霉(phytophthora infestans)孢子对植物接种。
将植物置于大约20℃且100%相对空气湿度的保温柜中。
接种3天后进行评估。0%指相当于对照物的效力,而100%的效力表示没有发现侵害。
下面的表中列出了活性化合物,活性化合物浓度和试验结果。
表B
疫霉试验(蕃茄)/保护
表B(续)
表B(续)
表B(续)
疫霉试验(蕃茄)/保护实施例C
单轴霉试验(葡萄)/保护
溶剂:4.7份重量丙酮
乳化剂:0.3份重量烷基-芳基聚乙二醇醚
为了生产活性化合物的合适的制剂,将1份重量的活性化合物与上述量的溶剂和乳化剂混合,将乳油用水稀释至所需浓度。
为了试验保护活性,用活性化合物制剂对小植物喷雾至液珠滴落。喷雾层风干后,用葡萄生单轴霉(Plasmopara viticola)孢子的水悬浮液对植物接种,然后在20-22℃且100%相对空气湿度的潮湿的室中保持1天。接着将植物放在21℃且90%空气湿度的温室中生长5天。然后弄湿植物并放在潮湿的室中1天。
接种6天后进行评估。0%指相当于对照物的效力,而100%效力指没有发现侵害情况。
下面的表中列出了活性化合物,活性化合物浓度和试验结果。
表C
表C(续)
单轴霉试验(葡萄)/保护
表C(续)
单轴霉试验(葡萄)/保护
Claims (7)
X1、X2、X3和X4各自独立地代表氢、卤原子、氰基、硝基、烷基、卤代烷基、烷氧基、卤代烷氧基、烷硫基、卤代烷硫基、烷基亚磺酰基、卤代烷基亚磺酰基、烷基磺酰基、卤代烷基磺酰基、任意取代的环烷基、羟基羰基、烷基羰基、烷氧基羰基、环烷基羰基、环烷氧基羰基、代表或-Z-R5。其中
R3和R4各自独立地代表氢、烷基、卤代烷基、烷氧基烷基、烷基羰基、任意取代的芳基、任意取代的芳基羰基、任意取代的芳基磺酰基、任意取代的芳基氨基羰基或任意取代的芳基甲基磺酰基,或者
R3和R4与和它们相连的氮原子一起代表任意被烷基取代的可以包含另外一个氧原子或一个烷基亚氨基基团的杂环,
Q代表一个直接的键或一个羰基,
R5代表任意取代的芳基或者代表任意取代的杂环基,
Z代表一个直接的键,代表CH2、O、S、SO、SO2、CO或偶氮基,或者
代表-CO-O-,其中氧原子与芳基或杂环残基键联,或者
代表-SO2-O-,其中硫原子与芳基或杂环残基键联,或者
代表-S-CH2-SO2-,其中硫基的硫原子与芳基或杂环残基键联,或者
X2和X3一起代表有3或4个原子的任意取代的亚烷基链,其中一个或两个(不相邻)碳原子可以被氧原子置换,
R1代表氰基或下面的基团或
其中
R6代表烷基,卤代烷基或任意被卤素和/或卤代烷基取代的苄基,
R2代表任意取代的杂环基,
Y代表一个直接的键,代表-CH2-、-CH2-CH2-、-CO-、-SO2-、-CO-O-或-SO-O-,其中在后两个基团的情况下碳原子或硫原子与咪唑环的氮原子键合,和其酸加成盐和金属盐配合物。
2.权利要求1的式(I)苯并咪唑衍生物,其中
X1、X2、X3和X4各自独立地代表氢、氟、氯、溴、碘、氰基、硝基,有1-8个碳原子的直链或支链烷基,有1-6个碳原子和1-13个相同或不同卤原子的直链或支链卤代烷基,有1-8个碳原子的直链或支链烷氧基,有1-6个碳原子和1-13个相同或不同卤原子的直链或支链卤代烷氧基,有1-8个碳原子的直链或支链烷硫基,有1-6个碳原子和1-13个相同或不同卤原子的直链或支链卤代烷硫基,有1-8个碳原子的直链或支链烷基亚磺酰基,有1-6个碳原子和1-13个相同或不同卤原子的直链或支链卤代烷基亚磺酰基,有1-8个碳原子的直链或支链烷基磺酰基,有1-6个碳原子和1-13个相同或不同卤原子的直链或支链卤代烷基磺酰基,有3-6个碳原子的环烷基,该环烷基可有可无地被相同或不同的选自卤素和具有1-4个碳原子的烷基一元至五元取代,代表羟基羰基,在直链或支链烷基部分具有1-6个碳原子的烷基羰基,在直链或支链烷氧基部分具有1-6个碳原子的烷氧羰基,在环烷基具有3-6个碳原子的环烷基羰基,在环烷基部分具有3-6个碳原子的环烷氧基羰基,代表
或-Z-R5
R3和R4各自独立地代表氢,具有1-6个碳原子的直链或支链烷基,具有1-6个碳原子和1-13个相同或不同卤原子的直链或支链卤代烷基,在烷氧基部分有1-4个碳原子且在烷基部分有1-4个碳原子的直链或支链烷氧基烷基,在直链或支链烷基部分具有1-6个碳原子的烷基羰基,具有6-10个碳原子的芳基,在芳基部分有6-10个碳原子的芳基羰基,具有6-10个碳原子的芳基磺酰基,芳基部分有6-10个碳原子的芳基氨基羰基,或者代表芳基部分有6-10个碳原子的芳基甲基磺酰基,上述的每一个芳基残基可以是被相同或不同的选自下列的基团一元至三元取代的:卤素、氰基、硝基,有1-4个碳原子的烷基,有1-4个碳原子的烷氧基,有1-4个碳原子的烷硫基,有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基,有1-4个碳原子和1-5个相同或不同卤原子的卤代烷氧基,具有1-4个碳原子和1-5个相同或不同卤原子的卤代烷硫基,有1-4个碳原子的烷基亚磺酰基,有1-4个碳原子的烷基磺酰基,具有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基亚磺酰基,和具有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基磺酰基,和
另外,R3和R4与它们连接的氮原子一起优选代表5元或六元杂环,其可有可无地被具有1-4个碳原子的烷基一元至三元取代,并且其可以另外含有一个氧原子或一个C1-C4烷基亚氨基,
Q代表一个直接的键或者代表一个羰基,
R5代表具有6-10个碳原子的芳基,每一个这样的残基可能被相同或不同的选自下组的取代基一元至三元取代:卤素、氰基、硝基;具有1-4个碳原子的烷基,具有1-4个碳原子的烷氧基,具有1-4个碳原子的烷硫基,具有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基,具有1-4个碳原子和1-5个相同或不同卤原子的卤代烷氧基,具有1-4个碳原子和1-5个相同或不同卤原子的卤代烷硫基,具有1-4个碳原子的烷基亚磺酰基,具有1-4个碳原子的烷磺酰基,具有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基亚磺酰基,和具有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基磺酰基,或者
R5代表5元或6元且含有1-3个杂原子例如氮原子、氧原子和/或硫原子的饱和或不饱和杂环残基,这些残基可能是被相同或不同的下组取代基一元至三元取代的:卤素,有1-4个碳原子的烷基,有1-4个碳原子的烷氧基,有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基,有1-4个碳原子和1-5个相同或不同卤原子的卤代烷氧基,在烷氧基部分有1-3个碳原子的烷氧羰基,有3-6个碳原子的环烷基,氰基和硝基,
Z代表一个直接的键,也代表CH2、O、S、SO、SO2、CO或偶氮基团,或者
代表-CO-O-,其中氧原子与芳基或杂环残基键合,或者
代表-SO2-O-、其中硫原子与芳基或杂环残基键合,或者
代表-S-CH2-SO2-,其中硫代基团中的硫原子与芳基或杂环残基键合,
X2和X3一起也代表有3或4个碳原子的亚烷基,其可有可无地被卤素,有1-4个碳原子的烷基和/或1-4个碳原子和1-9个卤原子的卤代烷基一元至六元取代,其中一个或两个(不相邻)碳原子可以被氧原子置换,
R6代表1-4个碳原子的直链或支链烷基,有1-4个碳原子和1-9个相同或不同卤原子的直链或支链卤代烷基,或者代表苄基,苄基可有可无地被相同或不同的选自卤素和有1或2个碳原子和1-5个相同或不同卤原子的卤代烷基的取代基一元至三元取代,
R2代表5元或6元有1-3个杂原子例如氮原子,氧原子和/或硫原子的饱和或不饱和的,可有可无地与苯环稠合的杂环残基,这些残基可以被下组相同或不同的取代基一元至三元取代:卤素、氰基、硝基、羟基、氨基、甲酰基、羧基、氨基甲酰基、硫代氨基甲酰基,有1-4个碳原子的烷基,有1-4个碳原子的烷氧基,有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基,有1-4个碳原子和1-5个相同或不同卤原子的卤代烷氧基,烷氧基部分有1-4个碳原子的烷氧羰基,有3-6个碳原子的环烷基,有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基亚磺酰基,有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基磺酰基,有1-4个碳原子的烷基氨基,有1-4个碳原子的羟基烷基氨基,在每个烷基中有1-4个碳原子的二烷基氨基,烷基部分有1-4个碳原子的烷基羰基,烷基基团中有1-4个碳原子的烷基羰基氨基,烷基部分有1-4个碳原子的羟基亚氨基烷基,烷氧基部分有1-4个碳原子且在烷基部分有1-4个碳原子的烷氧亚氨基烷基,烷基部分有1-4个碳原子的烷基羰基氧基,以及卤代烷基中有1-4个碳原子和1-5个相同或不同卤原子的卤代烷基羰基氧基,
这些杂环残基可以含有氧代基团,
Y代表一个直接的键,代表CH2、CH2-CH2、CO、SO2、-CO-O-或-SO-O-,其中在后两个基团的情况下,碳原子或硫原子与咪唑环中的氮原子键合。
3.一种制备权利要求1式(I)苯并咪唑衍生物及其酸加成盐和金属盐配合物的方法,特征在于式(II)氰基苯并咪唑其中
X1、X2、X3和X4各如上所定义,
与式(III)Hal-Y-R2的卤代物反应,
其中R2和Y各如上文定义,
Hal代表氯或溴,
而且,如果适当,存在一种酸结合剂和如果适当存在一种稀释剂,所得的下式苯并咪唑其中
R2、Y、X1、X2、X3和X4各如上文所定义,如果合适,任选其一地
a)存在一种酸结合剂和存在一种稀释剂下与硫化氢反应,或者
b)在存在一种酸结合剂和存在一种稀释剂下,与式(IV)H-S-R6硫化合物反应,其中
R6如上文所定义,以及如果适当,向所得式(I)化合物中加入一种酸或一种金属盐。
4.杀微生物组合物,特征在于含有一定量的至少一种权利要求1的式(I)苯并咪唑衍生物或者式(I)的苯并咪唑衍生物的一种酸加成盐或金属盐配合物。
5.权利要求1的式(I)苯并咪唑衍生物或其酸加成盐或金属盐配合物作为农作物保护和材料保护中的杀微生物剂的用途。
6.在农作物保护和材料保护中控制所不期望微生物的方法,特征在于对微生物和/或其定居地施用权利要求1的式(I)苯并咪唑衍生物或其酸加成盐或金属盐配合物。
7.制备杀微生物组合物的方法,特征在于将权利要求1的式(I)苯并咪唑衍生物或其酸加成盐或金属盐配合物与补充剂和/或表面活性化合物混合。
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CN107041373A (zh) * | 2017-05-09 | 2017-08-15 | 李洪军 | 一种农作物用长效杀菌剂 |
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CN107041373A (zh) * | 2017-05-09 | 2017-08-15 | 李洪军 | 一种农作物用长效杀菌剂 |
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