CN1258284A - 氟代甲氧基亚氨基化合物 - Google Patents
氟代甲氧基亚氨基化合物 Download PDFInfo
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- CN1258284A CN1258284A CN98805658A CN98805658A CN1258284A CN 1258284 A CN1258284 A CN 1258284A CN 98805658 A CN98805658 A CN 98805658A CN 98805658 A CN98805658 A CN 98805658A CN 1258284 A CN1258284 A CN 1258284A
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- alkyl
- methyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 claims abstract description 41
- -1 alkyl sulfide Chemical compound 0.000 claims description 151
- 229910052760 oxygen Inorganic materials 0.000 claims description 51
- 239000001301 oxygen Substances 0.000 claims description 50
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 41
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 34
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 29
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 239000011737 fluorine Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 20
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 230000009977 dual effect Effects 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 239000005864 Sulphur Substances 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 239000013543 active substance Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 10
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 8
- JSLZUBLGGPEVQN-DIPNUNPCSA-N (2r)-4-methyl-2-propan-2-yl-2-[2-[4-[4-[2-(3,4,5-trimethoxyphenyl)ethyl]piperazin-1-yl]butoxy]phenyl]-1,4-benzothiazin-3-one Chemical compound COC1=C(OC)C(OC)=CC(CCN2CCN(CCCCOC=3C(=CC=CC=3)[C@@]3(C(N(C)C4=CC=CC=C4S3)=O)C(C)C)CC2)=C1 JSLZUBLGGPEVQN-DIPNUNPCSA-N 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 6
- 125000005336 allyloxy group Chemical group 0.000 claims description 6
- ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 229950001891 iprotiazem Drugs 0.000 claims description 6
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 6
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 6
- RFPMGSKVEAUNMZ-UHFFFAOYSA-N pentylidene Chemical group [CH2+]CCC[CH-] RFPMGSKVEAUNMZ-UHFFFAOYSA-N 0.000 claims description 6
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 claims description 6
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 5
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 5
- 241000607479 Yersinia pestis Species 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 3
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 3
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 3
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 3
- 241000238631 Hexapoda Species 0.000 claims description 2
- 239000003905 agrochemical Substances 0.000 claims description 2
- 238000010572 single replacement reaction Methods 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 8
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 2
- 239000013067 intermediate product Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 238000002474 experimental method Methods 0.000 description 29
- 239000000463 material Substances 0.000 description 26
- 150000001721 carbon Chemical group 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 19
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 241000233866 Fungi Species 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 241000209140 Triticum Species 0.000 description 12
- 235000021307 Triticum Nutrition 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 241000894006 Bacteria Species 0.000 description 10
- 240000006365 Vitis vinifera Species 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 239000003995 emulsifying agent Substances 0.000 description 10
- 241000221300 Puccinia Species 0.000 description 9
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 9
- 235000009754 Vitis X bourquina Nutrition 0.000 description 9
- 235000012333 Vitis X labruscana Nutrition 0.000 description 9
- 235000014787 Vitis vinifera Nutrition 0.000 description 9
- 150000003851 azoles Chemical class 0.000 description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 150000001241 acetals Chemical class 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
- 244000005700 microbiome Species 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 240000007594 Oryza sativa Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 241001123569 Puccinia recondita Species 0.000 description 5
- 150000004703 alkoxides Chemical class 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 4
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical group CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000001720 action spectrum Methods 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000003899 bactericide agent Substances 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 239000012973 diazabicyclooctane Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound 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 4
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- 239000003456 ion exchange resin Substances 0.000 description 4
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- 229940031815 mycocide Drugs 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 235000015320 potassium carbonate Nutrition 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- 241000588698 Erwinia Species 0.000 description 3
- 229920004449 Halon® Polymers 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
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- 150000004867 thiadiazoles Chemical class 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229940074152 thuringiensin Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- 238000012546 transfer Methods 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
- JWXZLCFGVKMEEK-UHFFFAOYSA-N triarathene Chemical compound C1=CC(Cl)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 JWXZLCFGVKMEEK-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
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009369 viticulture Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/52—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/20—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with no nitrogen atoms directly attached to a ring carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
- C07D251/52—Two nitrogen atoms with an oxygen or sulfur atom attached to the third ring carbon atom
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- C—CHEMISTRY; METALLURGY
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- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
Abstract
本发明涉及新的氟甲氧亚氨基化合物,其制备方法和其作为农药的用途,还涉及新的中间体及其多种制备方法。
Description
本发明涉及新的氟代甲氧基亚氨基化合物、其制备方法及其作为农药的用途,还涉及新的中间体和其制备方法。
已知某些结构上类似于下述化合物的氟代甲氧基亚氨基化合物具有杀真菌特性(例如,对照WO95/17376和DE-9611653)。然而在许多情况下,这些化合物的杀真菌活性是不令人满意的。
因此本发明提供具有通式(I)的新的氟代甲氧基亚氨基化合物。
其中
Q1代表氧或-NH-,
其中
Ar代表任选被取代的芳基,
Q2代表氧或硫,
X代表氢或卤素和
L1,L2,L3和L4是相同或不同的并且彼此独立地代表氢、卤素、氰基、硝基,在所有情况下任选被卤代的烷基、烷氧基、烷基硫基、烷基亚磺酰或烷基磺酰基。
芳基优选代表芳香族的单环或多环烃环,如特别是苯基、萘基、蒽基、菲基,优选苯基或萘基,特别是苯基。
卤素优选代表氟、氯、溴或碘,特别是氟、氯或溴。
而且已发现当(方法a)通式(II)的羟基芳基化合物
其中
Q1,L1,L2,L3和L4均如上所述,
其中
Ar,Q2和X均如上所述并
X1,X2,X3,X4,X5和X6代表卤素、烷基磺酰基或芳基磺酰基,
适当时在酸性受体和适当时在稀释剂存在下反应,得到通式(I)代表的新的氟代甲氧基亚氨基化合物。
也可能得到通式(I)的其中Q1是NH的氟代甲氧基亚氨基化合物的方法(方法a1)是将根据本发明通式(I)的其中Q1是氧的氟代甲氧基亚氨基化合物与甲胺反应,适当时在稀释剂例如甲醇、乙醇或四氢呋喃的存在下。
最后,还发现通式(I)的氟代甲氧基亚氨基化合物具有非常好的杀微生物特性并且可用于保护植物不受有害生物的伤害。
令人惊讶的是本发明的物质比现有技术中具有相同的作用方向,结构相似的活性化合物具有更好的活性。
适当时本发明的化合物可以不同的可能异构体,特别是立体异构体的混合物形式存在,例如E和Z。要求保护的包括E和Z异构体以及这些异构体的任何形式的混合物。
本发明优选提供通式(I)的化合物,其中
Q1代表氧或-NH-,
Ar代表任选地单至三取代的苯基或任选地单至四取代的萘基,其中可能的取代基优选选自下列基团:
卤素,氰基,硝基,氨基,羟基,巯基,在所有情况下含1-6个碳原子的直链或支链的烷基、烷氧基、烷基硫基、烷基亚磺酰基或烷基磺酰基,在所有情况下含有2-6个碳原子的直链或支链烯基、烯氧基或炔氧基,在所有情况下含1-6个碳原子和1-13个相同或不同的卤素原子的直链或支链卤代烷基、卤代烷氧基,卤代烷基硫基、卤代烷基亚磺酰基或卤代烷基磺酰基,在所有情况下含2-6个碳原子和1-11个相同或不同的卤素原子的直链或支链卤代烯基或卤代烯氧基,在所有情况下在各个烷基部分含1-6个碳原子的直链或支链的烷基氨基、环烷基氨基、二烷基氨基、烷基羰基或烷基羰基氧基、烷氧基羰基、烷基磺酰基氧基、羟亚氨基烷基或烷氧基亚氨基烷基,在所有情况下含1-6个碳原子并所有情况下任选被相同或不同取代基单取代或多取代的双重连接的(zweifach verknüpftes)亚烷基或二氧亚烷基,取代基选自卤素、含1-4个碳原子的直链或支链烷基和含1-4个碳原子及1-9个相同或不同的卤素原子的直链或支链卤代烷基,在所有情况下含3-7个碳原子并所有情况下任选被1-4个卤素原子取代的环烷基、环烯基、环烷氧基或环烯基氧基,和通过氮原子相连的饱和杂环基,
Q2代表氧或硫,
X代表氢、氟、氯或溴和
L1,L2,L3和L4是相同或不同的并彼此独立地代表氢、卤素、氰基、硝基,代表在所有情况下含1-6个碳原子并各种情况下任选被1-5个卤素原子取代的烷基、烷氧基、烷基硫基、烷基亚磺酰基或烷基磺酰基。
在定义中,饱和或不饱和烃链如烷基、烯基或炔基在所有情况下都是直链或支链的,包括与杂原子结合,如烷氧基、烷基硫基或烷基氨基。
环烷基代表饱和碳环环状化合物,适当时与其他碳环、稠环或桥环形成多环环状体系。
本发明特别涉及通式(I)的化合物,其中
Q1代表氧或-NH-,
Ar代表任选被相同或不同的取代基单取代或二取代的苯基,其中可能的取代基优选选自下列基团:
氟,氯,溴,氰基,硝基,甲基,乙基,正或异丙基,正-、异-、仲-或叔-丁基,丙烯基,丁-3-烯-2-基,2-甲基丙烯基,环丙基,甲氧基,乙氧基,正或异丙氧基,烯丙氧基,甲硫基,乙硫基,正或异丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,三氟甲硫基,二氟氯甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲氧基羰基,乙氧基羰基,甲氧亚胺基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基,乙氧亚氨基乙基,在所有情况下双重连接的亚丙基,亚丁基或亚戊基,或在所有情况下双重连接的亚甲二氧基或亚乙二氧基,并且任选地均可被相同或不同的取代基单取代至四取代,取代基选自氟、氯、甲基、三氟甲基和乙基。
Q2代表氧或硫,
X代表氢、氟或氯及
L1,L2,L3和L4可以是相同或不同的并彼此独立地代表氢、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、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基。
特别优选地,是通式(I)化合物,其中
Q1代表氧或-NH-,
其中
Ar代表任选地被相同或不同的取代基单取代或二取代的苯基,其中可能的取代基优选选自下列基团:
氟,氯,溴,氰基,硝基,甲基,乙基,正或异丙基,正-、异-、仲-或叔-丁基,丁-3-烯-2-基,2-甲基丙烯基,环丙基,甲氧基,乙氧基,正或异丙氧基,烯丙氧基,甲硫基,乙硫基,正或异丙硫基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,三氟乙氧基,二氟甲硫基,三氟甲硫基,甲氧基羰基,乙氧基羰基,甲氧亚胺基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基,乙氧亚氨基乙基,在所有情况下双重连接的亚丙基,亚丁基或亚戊基,或在所有情况下双重连接的亚甲二氧基或亚乙二氧基,并且均可被相同或不同的取代基任选单取代至四取代,取代基选自氟、氯、甲基、三氟甲基和乙基。
Q2代表氧或硫,
X代表氢、氟或氯及
L1和L3可以是相同或不同的并彼此独立地代表氢或甲基和
L2和L4代表氢。
在通式(I)中
Q1优选代表氧,特别是代表-NH-。
在通式(I)中
其中在所有情况下
Q2优选代表氧并特别代表硫,
X优选代表氢或卤素并特别代表氟和
Ar优选代表未取代或单取代至三取代的苯基或未取代或单取代至四取代的萘基,特别代表单取代或二取代的苯基。
Ar的取代基优选选自下列基团:
卤素,氰基,硝基,氨基,羟基,巯基,在所有情况下含1-6个碳原子的直链或支链的烷基、烷氧基、烷基硫基、烷基亚磺酰基或烷基磺酰基,在所有情况下含有2-6个碳原子的直链或支链烯基、烯氧基或炔氧基,在所有情况下含1-6个碳原子和1-13个相同或不同的卤素原子的直链或支链卤代烷基、卤代烷氧基、卤代烷基硫基、卤代烷基亚磺酰基或卤代烷基磺酰基,在所有情况下含2-6个碳原子和1-11个相同或不同的卤素原子的直链或支链卤代烯基或卤代烯氧基,在所有情况下在各个烷基部分含1-6个碳原子的所有情况下直链或支链的烷基氨基、环烷基氨基、二烷基氨基、烷基羰基、烷基羰基氧基、烷氧基羰基、烷基磺酰基氧基、羟亚氨基烷基或烷氧基亚氨基烷基,在所有情况下含1-6个碳原子并所有情况下任选被相同或不同取代基单取代或多取代的双重连接的亚烷基或二氧亚烷基,取代基选自卤素和/或含1-4个碳原子的直链或支链烷基和/或含1-4个碳原子及1-9个相同或不同的卤素原子的直链或支链卤代烷基,在所有情况下含3-7个碳原子并所有情况下任选被1-4个卤素原子取代的环烷基、环烯基、环烷氧基或环烯基氧基,和通过氮原子相连的饱和杂环基。
Ar的取代基特别选自下列基团:
氟,氯,溴,氰基,硝基,甲基,乙基,正或异丙基,正-、异-、仲-或叔-丁基,丙烯基,丁-3-烯-2-基,2-甲基丙烯基,环丙基,甲氧基,乙氧基,正或异丙氧基,烯丙氧基,甲硫基,乙硫基,正或异丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,三氟甲硫基,二氟氯甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲氧基羰基,乙氧基羰基,甲氧亚胺基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基,乙氧亚氨基乙基,在所有情况下双重连接的亚丙基,亚丁基或亚戊基,或在所有情况下双重连接的亚甲二氧基或亚乙二氧基,并且任选地均可被相同或不同的取代基单取代至四取代,取代基选自氟、氯、甲基、三氟甲基和乙基。
Ar的取代基特别优选选自下列基团:
氟,氯,溴,氰基,硝基,甲基,乙基,正或异丙基,正-、异-、仲-或叔-丁基,丁-3-烯-2-基,2-甲基丙烯基,环丙基,甲氧基,乙氧基,正或异丙氧基,烯丙氧基,甲硫基,乙硫基,正或异丙硫基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,三氟乙氧基,二氟甲硫基,三氟甲硫基,甲氧基羰基,乙氧基羰基,甲氧亚胺基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基,乙氧亚氨基乙基,在所有情况下双重连接的亚丙基,亚丁基或亚戊基,或在所有情况下双重连接的亚甲二氧基或亚乙二氧基,并且均可任选地被相同或不同的取代基单取代至四取代,取代基选自氟、氯、甲基、三氟甲基和乙基。
在通式(I)中
L1和L3是相同或不同的并彼此独立地优选代表氢、卤素、氰基、硝基,代表在所有情况下含1-6个碳原子并所有情况下任选被1-5个卤素原子取代的烷基、烷氧基、烷基硫基、烷基亚磺酰基或烷基磺酰基,并且特别代表氢。
在通式(I)中
L2和L4是相同或不同的并彼此独立地优选代表氢、卤素、氰基、硝基,代表在所有情况下含1-6个碳原子并所有情况下任选被1-5个卤素原子取代的烷基如特别是甲基、烷氧基、烷基硫基、烷基亚磺酰基或烷基磺酰基并且特别代表氢。
上述一般或优选的基团定义不仅适用于通式(I)的终产物并且相应地适用于制备过程中所有情况下所需的原料或中间体。
不依赖于所有情况下给出的组合,特别为这些基团在各组合或优选组合中给出的基团定义也可被其他优选范围的基团定义所代替。
根据本发明进行方法a)所需的原料羟基芳基化合物的一般定义由通式(II)给出。在通式(II)中,Q1,L1,L2,L3和L4优选或特别具有与本发明通式(I)化合物的相关描述中提到作为优选或特别优选的Q1,L1,L2,L3和L4的那些意义。
通式(II)的羟基芳基化合物还没有被公开;作为新物质,它们形成了本申请主题的一部分。
通式(II)的羟基芳基化合物(方法b)是通过水解通式(IX)的缩醛得到的
其中
R1代表烷基,
R2代表氢或烷基或
R1和R2与它们相连的原子一起代表一个五元或六元杂环并且
Q1,L1,L2,L3和L4均如上所述,
适当时在稀释剂的存在下,稀释剂优选脂族烃、脂环烃或芳香烃,例如石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或萘烷;卤化烃,例如氯苯、二氯苯、二氯甲烷、氯仿、四氯甲烷、二氯乙烷或三氯乙烷;醚,例如二乙醚、二异丙醚、二氧己环、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;腈,如乙腈、丙腈、正或异丁腈或苄腈;酯,如乙酸甲酯或乙酸乙酯;砜,如环丁砜;醇,如甲醇、乙醇、正或异丙醇、正-、异-、仲-或叔-丁醇、乙二醇、丙基-1,2-二醇、乙氧基乙醇、甲氧基乙醇、二乙二醇一甲醚、二乙二醇一乙醚,它们与水的混合物或纯水。
并且适当时在酸的存在下,酸优选无机或有机质子酸或路易斯酸,例如氯化氢、溴化氢、硫酸、磷酸、甲酸、乙酸、三氟乙酸、甲磺酸、三氟甲磺酸、甲苯磺酸、三氟化硼(也当作醚合物)、三溴化硼、三氯化铝、三溴化铝、氯化锌、氯化铁(III)、五氯化锑,或聚合酸,例如酸性离子交换剂、酸性氧化铝或酸性二氧化硅,
温度为-20℃至120℃,优选温度为-10℃至80℃。
其中Q1是NH的通式(II)的羟基芳基化合物还可通过(方法b1)将其中Q1是氧的通式(II)的羟基芳基化合物与甲胺反应,适当时可在稀释剂的存在下,例如甲醇、乙醇或四氢呋喃。
根据本发明进行方法b)所需的原料缩醛的一般定义由通式(IX)给出。在通式(IX)中,Q1,L1,L2,L3和L4优选或特别代表的含义在与本发明通式(I)化合物的相关描述中提到的该通式中优选或特别优选的Q1,L1,L2,L3和L4相同。R1代表烷基,优选代表甲基或乙基,R2代表氢或烷基,优选代表甲基或乙基,或R1和R2与它们相连的原子一起代表一个五元或六元杂环,优选代表四氢呋喃基或四氢吡喃基。
通式(IX)的缩醛还没有被公开;作为新物质,它们形成了本申请主题的一部分。
其中
R1,R2,Q1,L1,L2,L3和L4均如上所述,
最初与亚硝基化剂反应,优选碱金属亚硝酸盐,例如亚硝酸钠,或特别是与亚硝酰氯或亚硝酸烷基酯反应,例如亚硝酸叔丁基酯或亚硝酸叔戊酯,适当时在稀释剂的存在下,稀释剂优选酯类,例如乙酸甲酯或乙酸乙酯,或醇类,例如甲醇或乙醇,并且适当时在酸性受体存在下,酸性受体优选碱金属氢氧化物、碳酸盐或醇盐,例如甲醇钠或乙醇钠,温度为-50℃至100℃,优选-20℃至50℃,
其中
R1,R2,Q1,L1,L2,L3和L4均如上所述,
优选不用氟溴甲烷或氟氯甲烷进一步处理,
适当时在稀释剂的存在下,稀释剂优选脂族烃、脂环烃或芳香烃,例如石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或萘烷;卤化烃,例如氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;醚,如乙醚、二异丙醚、甲基叔丁醚、甲基叔戊醚、二氧己环、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;酮,如丙酮、丁酮、甲基异丁酮或环己酮;腈,如乙腈、丙腈、正或异丁腈或苄腈;酯如乙酸甲酯或乙酸乙酯;酰胺,如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酰三胺;亚砜,如二甲基亚砜;砜,如环丁砜;醇,如甲醇、乙醇、正或异丙醇、正-、异-、仲或叔丁醇、乙二醇、丙基-1,2-二醇、乙氧基乙醇、甲氧基乙醇、二乙烯乙二醇一甲醚、二乙烯乙二醇一乙醚,它们与水的混合物或纯水,并且适当时在碱的存在下,碱优选碱土金属氢化物、氢氧化物、氨化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐或碱金属氢化物、氢氧化物、氨化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐,例如氢化钠、氨化钠、甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾、氢氧化铵、乙酸钠、乙酸钾、乙酸钙、乙酸铵、碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠或碳酸铵,或叔胺,如三甲胺、三乙胺、N,N-二甲基苯胺、N,N-二甲基-苯甲胺、吡啶、N-甲基哌啶、N-甲基吗啉、N,N-二甲基氨基吡啶、二氮二环辛烷(DABCO)、二氮二环壬烯(DBN)或二氮二环十一碳烯(DBU),
并且适当时在催化剂存在下,催化剂优选路易斯酸,例如氯化铁(III)、氯化铝或溴化铝,
温度为-20℃至120℃,优选-10℃至80℃。
其中Q1是NH的通式(IX)的缩醛还可通过(方法c1)将其中Q1是氧的通式(IX)的缩醛与甲胺反应获得,适当时在稀释剂的存在下,例如甲醇、乙醇或四氢呋喃。
根据本发明进行方法c)来制备通式(IX)的缩醛所需的原料芳基乙酸衍生物的一般定义由通式(X)给出。在通式(X)中,Q1,L1,L2,L3和L4优选或特别代表的含义在与本发明通式(I)化合物的相关描述中提到的该通式中优选或特别优选的Q1,L1,L2,L3和L4相同。R1和R2优选代表在与通式(IX)化合物的相关描述中提到的优选的含义。
通式(X)的芳基乙酸衍生物是已知的和/或可由已知方法制备(例如对照J.Org.Chem.1994,203-13,和DE-9611653)。
根据本发明进行方法a)还需要的原料杂环衍生物的一般定义由通式(III)、(IV)、(V)、(VI)、(VII)和(VIII)给出。在通式(III)、(IV)、(V)、(VI)、(VII)和(VIII)中,Ar、Q2和X优选或特别代表的含义在与本发明通式(I)化合物的相关描述中提到的该通式中优选或特别优选的Ar、Q2和X相同。X1、X2、X3、X4、X5和X6彼此独立地代表卤素,优选代表氟或氯,或代表烷基磺酰或芳基磺酰基,优选代表甲基磺酰基、苯甲基磺酰基或甲苯基磺酰基。
通式(III)、(IV)、(V)、(VI)、(VII)和(VIII)的杂环衍生物是已知合成方法的化合物和/或可由已知工艺制备(例如对照J.Heterocyclic Chem.30,357(1993),J.Chem.Soc.,1955;3478,3480,Chem.Ber.,97,225-237,(1964),DE-9611653)。
根据本发明实施方法a)适用的稀释剂是所有的惰性有机溶剂。优选包括脂族烃、脂环烃或芳香烃,例如石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或萘烷;卤化烃,例如氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;醚类,如乙醚、二异丙醚、甲基叔丁醚、甲基叔戊醚、二氧己环、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;酮类,如丙酮、丁酮、甲基异丁酮或环己酮;腈类,如乙腈、丙腈、正丁腈或异丁腈或苄腈;酰胺,如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺,N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酰三胺;酯类,如乙酸甲酯或乙酸乙酯;亚砜,如二甲基亚砜;砜如环丁砜;醇,如甲醇、乙醇、正或异丙醇、正-、异-、仲或叔丁醇、乙二醇、丙基-1,2-二醇、乙氧基乙醇、甲氧基乙醇、二乙烯乙二醇一甲醚、二乙烯乙二醇一乙醚,它们与水的混合物或纯水。
根据本发明方法a)适当时在合适的酸性受体的存在下进行。合适的酸性受体是所有的通常的无机或有机碱。优选包括碱土金属氢化物、氢氧化物、氨化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐或碱金属氢化物、氢氧化物、氨化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐,例如氢化钠、氨化钠、甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾、氢氧化铵、乙酸钠、乙酸钾、乙酸钙、乙酸铵、碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠或碳酸铵,以及叔胺,如三甲胺、三乙胺、三丁基胺,N,N-二甲基苯胺、N,N-二甲基-苯甲胺、吡啶、N-甲基哌啶、N-甲基吗啉、N,N-二甲基氨基吡啶、二氮二环辛烷(DABCO)、二氮二环壬烯(DBN)或二氮二环十一碳烯(DBU)。
实施根据本发明的方法a)时的反应温度可在相当宽的范围内变化。通常,反应温度是0-150℃,优选温度0-80℃。
制备本发明通式(I)化合物的方法a)中,相对于每摩尔通式(II)的羟基芳基化合物使用通常为0.2-0.5摩尔,优选0.5-2摩尔的通式(III)、(IV)、(V)、(VI)、(VII)或(VIII)的杂环衍生物。
根据本发明的所有方法一般均在大气压下进行。然而也可以在升高或降低通常0.1bar至10bar的压力下进行。
反应的实施和反应产物的后处理及分离均按照已知方法进行(也参见制备实施例)。
根据本发明的物质具有有效的杀微生物活性并可用于在植物保护和材料保护中防治有害微生物,如真菌和细菌。
杀真菌剂可用于在植物保护中防治Plasmodiophoromycetes、卵菌亚纲、壶菌纲、接合菌亚纲、子囊菌纲、担子菌纲和半知菌纲真菌。
杀细菌剂可用于在植物保护中防治假单胞菌科、根瘤菌科、肠杆菌科、棒状杆菌科和链霉菌科细菌。
下文以实例列出了一些导致真菌性或细菌性病害的病原体的属名,但并不仅限于下文所列:
黄单胞菌属,例如田野黄单孢菌(Xanthomonas campestris)pv.稻黄单孢菌(Xanthomonas oryzae);
假单胞菌属,例如丁香假单孢菌(Pseudomonas syringae)pv.黄瓜角斑病假单孢菌(Pseudomonas lachrymans);
欧文氏菌属,例如解淀粉欧文氏菌(Erwinia amyloyora);
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);
盘梗霉属,例如莴苣盘梗霉(Bremia lactucae);
霜霉属,例如豌豆霜霉(Peronospora pisi)或芸苔霜霉(Peronosporabrassicae);
白粉菌属,例如禾白粉菌(Erysiphe graminis);
单丝壳属,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(Pyrenophora graminea)(分生孢子形式:Dreschslera,syn:长蠕孢属)
旋孢霉属,例如禾旋孢霉(Cochliobolus sativus)(分生孢子形式:Dreschslera,syn:长蠕孢属)
单孢锈属,例如疣顶单孢锈菌(Uromyces appendiculatus);
柄锈属,例如隐匿柄锈菌(Puccinia recondita);
核盘菌属,例如油菜核盘菌(Sclerotinia sclerotiorum);
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(Ustilago avenae);
薄膜革菌属,例如佐佐木氏薄膜革菌(Pellicularia sasakii);
Pyricularia species,例如Pyricularia oryzae;
镰孢霉属,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,例如颍枯壳针孢(Septoria nodorum);
小球腔菌属,例如颍枯小球腔菌(Leptosphaeria nodorum);
尾孢菌属,例如Cercospora canescens;
链格孢属,例如甘蓝黑斑病链格孢(Alternaria brassicae);
Pseudocercosporella species,例如Pseudocercosporellahepotrichoides。
由于植物可以忍耐防治植物病害所需浓度的活性化合物,因此允许处理植物的地上部分、繁殖根状茎和种子以及土壤。
本发明的活性化合物可以特别成功地用于防治谷类病害,例如柄锈属病害,以及防治葡萄栽培和水果及蔬菜种植中的病害,例如黑星菌属和单轴霉属病害。此外,根据本发明的活性化合物还适用于增加作物产量。而且它们具有低毒性且植物对其具有良好的耐受性。
在材料的保护中,根据本发明的物质可用于保护工业材料不受有害微生物的感染和破坏。
本文中的工业材料应理解为用于工业使用而制备的非生物的材料。例如,打算用本发明活性化合物防止微生物的改变或破坏的工业材料可以是粘合剂、胶料、纸或纸板、纺织品、皮革、木材、油漆和塑料制品、冷却润滑剂和其他能被微生物感染或破坏的材料。可能由于微生物增殖受到损伤的生产设备的某些部分,例如冷却水循环系统也在受保护的材料范围内。本发明范围内提到的工业材料优选粘合剂、胶料、纸和纸板、皮革、木材、油漆、冷却润滑油和传热液,特别优选木材。
可以提到的能够降解或改变上述工业材料的微生物是,例如,细菌、真菌、酵母菌、藻类和粘菌生物(slime organisms)。
根据本发明的活性化合物优选作用于真菌,特别是霉菌、木材脱色和木材破坏真菌(担子菌纲)以及作用于粘菌生物和藻类。
下文以实例的方式列出微生物的属名:
链格孢属,如纤细链格孢(Alternaria tenuis);
曲霉属,如黑色曲霉(Aspergillus niger);
毛壳属,如球毛壳霉(Chaetomium globosum);
粉孢革菌属,如单纯粉孢革菌(Coniophora puetana);
香菇属,如虎皮香菇(Lentinus tigrinus);
青霉属,如灰绿青霉(Penicillium glaucum);
多孔属,如变色多孔菌(Polyporus versicolor);
短柄霉属,如出芽短柄霉(Aureobasidium pullulans);
Sclerophoma,如Sclerophoma pityophila;
木霉属,如绿色木霉(Trichoderma viride);
埃希氏杆菌属,如大肠埃希氏杆菌(Escherichia coli);
假单胞菌属,如铜绿假单胞菌(Pseudomonas aeruginosa);
葡萄球菌属,如金黄色葡萄球菌(Staphylococus aureus)。
根据其特殊的物理和/或化学特性,活性化合物可变成常用制剂,如溶液、乳浊液、悬浮液、粉剂、泡沫体、糊剂、颗粒剂、气雾剂以及包在聚合物中和用于种子的包衣组合物中的微囊,和ULV冷却和加温成雾制剂。
这些制剂是以已知的方式制造的,例如通过将活性化合物与填充剂混合,即液体溶剂、带压液化气和/或固体载体,可选择使用表面活性剂,即乳化剂和/或分散剂和/或泡沫形成剂。如果使用水为填充剂,还可使用例如有机溶剂作为辅助溶剂。下列主要是适于作为液体溶剂的:芳香烃如二甲苯、甲苯或烷基萘,氯代芳香烃或氯代脂族烃如氯苯、氯乙烯或二氯甲烷,脂族烃如环己烷或烷属烃例如石油馏分,醇类如丁醇或乙二醇和它们的醚和酯,酮类如丙酮、甲乙酮、甲基异丁酮或环己酮,强极性溶剂如二甲基甲酰胺或二甲基亚砜,或水。液化气填充剂或载体应理解为在标准温度和大气压下是气态的液体,例如气溶胶喷射剂如卤代烃或丁烷、丙烷、氮和二氧化碳。合适的固体载体为:例如磨细的天然材料如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱土或硅藻土,和磨细的合成材料如高分散硅石、氧化铝和硅酸盐。颗粒剂使用的合适的固体载体为:例如压碎和分级的天然岩石如方解石、大理石、浮石、海泡石、白云石或无机和有机粗淀粉合成颗粒,和有机材料的颗粒如锯屑、椰子壳、玉米芯和烟草杆。合适的乳化剂和/或泡沫形成剂是:例如非离子和阴离子乳化剂如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如烷基芳基聚乙二醇醚、烷基磺酸酯、烷基硫酸酯、芳基磺酸酯或蛋白水解产物。合适的分散剂是:例如木质素亚硫酸酯废液和甲基纤维素。
制剂中可使用粘合剂如羧甲基纤维素和粉末、颗粒或胶乳形式的天然和合成聚合物,如阿拉伯树胶、聚乙烯醇、聚乙酸乙烯酯或天然磷脂例如脑磷脂和卵磷脂以及合成磷脂。其他添加剂可以是矿物油和植物油。
可以使用着色剂,如无机色素,例如氧化铁、氧化钛、普鲁士蓝和有机染料如茜素染料、偶氮染料和金属酞菁染料以及微量营养物如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
制剂通常包含0.1-95重量百分比的活性化合物,优选0.5-90%。
根据本发明的活性化合物可以其自身或以制剂形式与已知杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀虫剂混合使用,以便拓宽作用谱或防止抗性发展。在多数情况下能实现协同效应,即混合物的效力超过单个组分的效力。
混合物中的联合组分的实例是下列化合物:
杀真菌剂:
aldimorph,氨丙磷酸,ampropylfos potassium,andoprim,敌菌灵,戊环唑,azoxystrobin,苯霜灵,麦锈灵,苯菌灵,benzamacril,benzamacryl-isobutyl,双丙氨膦,乐杀螨,联苯,联苯三唑醇,双瘟素,糠菌唑,乙嘧酚磺酸酯,丁硫啶,石硫合剂,capsimycin,敌菌丹,克菌丹,多菌灵,萎锈灵,carvon,quinomethionate,灭瘟唑,chlorfenazole,地茂散,氯化苦,百菌清,乙菌利,clozylacon,代森盐,霜脲氰,环丙唑醇,嘧菌环胺,酯菌胺,咪菌威,双氯酚,苄氯三唑醇,diclofluanid,哒菌酮,氯硝胺,乙霉威,苯醚甲环唑,二甲嘧酚,烯酰吗啉,烯唑醇,甲基烯唑醇,家蝇磷,联苯胺,吡菌硫,灭菌磷,二氰蒽醌,十二环吗啉,多果定,联氨噁唑酮,敌瘟磷,epoxiconazole,乙环唑,乙嘧酚,土菌灵,famoxadon,咪菌腈,氯苯嘧啶醇,腈苯唑,甲呋酰苯胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,三苯基酯酸锡,毒菌锡,福美铁,嘧菌腙,氟啶胺,flumetover,氟氯菌核利,氟喹唑,呋嘧醇,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,三乙膦酸铝,三乙膦酸钠,四氯苯酞,麦穗宁,呋霜灵,furametpyr,二甲呋酰胺,呋菌唑,呋醚唑,拌种胺,谷种定,毒菌酚,己唑醇,噁霜灵,抑霉唑,亚胺唑,双胍辛,iminoctadinealbesilate,双胍辛乙酸盐,iodocarb,ipconazole,异稻瘟净IBP,异菌脲,irumamycin,稻瘟灵,isovaledione,春雷霉素,kresoxim-methyl,铜制剂,如:氢氧化铜、环烷酸铜、王铜、硫酸铜、氧化铜、喹啉酮和波尔多液,代森锰铜,代森锰锌,代森锰,meferimzone,嘧菌胺,灭锈胺,甲霜灵,叶菌唑,磺菌威,呋菌胺,代森联,氯苯咯菌胺,噻菌胺,米多霉素,腈菌唑,甲菌利,福美镍,间硝酞异丙酯,氟苯嘧啶醇,呋酰胺,噁霜灵,oxamocarb,喹菌酮,氧化萎锈灵,oxyfenthiin,多效唑,稻瘟酯,戊菌唑,戊菌隆,氯瘟磷,多马霉素,哌丙灵,多抗霉素,polyoxorim,烯丙苯噻唑,咪鲜胺,腐霉利,霜霉威,propanosine-sodium,丙环唑,丙森锌,吡菌磷,啶斑肟,嘧霉胺,咯喹酮,氯吡呋醚,quinconazole,五氯硝基苯(PCNB),硫和硫制剂,戊唑醇,叶枯酞,四氯硝基苯,四环唑,四氟醚唑,噻菌灵,噻菌腈,thifluzamide,甲基硫菌灵,福美双,tioxymid,甲基立枯磷,甲苯氟磺胺,三唑酮,三唑醇,triazbutil,咪唑嗪,水杨菌胺,三环唑,十三吗啉,氟菌唑,嗪胺灵,灭菌唑,烯效唑,有效霉素,乙烯菌核利,烯霜苄唑,氰菌胺,代森锌,福美锌以及Dagger G,OK-8705,OK-8801,α-(1,1-二甲基乙基)-β-(2-苯氧乙基)-1H-1,2,4-三唑-1-乙醇,α-(2,4-二氯苯基)-β-氟代-b-丙基-1H-1,2,4-三唑-1-乙醇,α-(2,4-二氯苯基)-β-甲氧-a-甲基-1H-1,2,4-三唑-1-乙醇,α-(5-甲基-1,3-二氧己环-5-基)-β-[[4-(三氟甲基)-苯基]-亚甲基]-1H-1,2,4-三唑-1-乙醇,(5RS,6RS)-6-羟-2,2,7,7-四甲基-5-(1H-1,2,4-三唑-1-基)-3-辛酮,(E)-a-(甲氧亚氨基)-N-甲基-2-苯氧-苯基乙酰胺,{2-甲基-1-[[[1-(4-甲基苯基)-乙基]-氨基]-羰基]-丙基}-氨基甲酸1-异丙酯,1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)乙烷酮(ethanone)-O-(苯基甲基)-肟,1-(2-甲基-1-萘基)-1H-吡咯-2,5-二酮,1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯烷二酮,1-[(二碘甲基)-磺酰基]-4-甲基-苯,1-[[2-(2,4-二氯苯基)-1,3-二氧戊环-2-基]-甲基]-1H-咪唑,1-[[2-(4-氯苯基)-3-苯基环氧乙烷]-甲基]-1H-1,2,4-三唑,1-[1-[2-(2,4-二氯苯基)-甲氧基]-苯基]-乙烯基]-1H-咪唑,1-甲基-5-壬基-2-(苯基甲基)-3-吡咯烷醇,2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟-甲基-1,3-噻唑-5-甲酰苯胺,2,2-二氯-N-[1-(4-氯苯基)-乙基]-1-乙基-3-甲基-环丙烷甲酰苯胺,2,6-二氯-5-(甲基硫)-4-嘧啶基-硫代氰酸酯,2,6-二氯-N-(4-三氟甲基苯甲基)-苯甲酰胺,2,6-二氯-N-[[4-(三氟甲基)-苯基]-甲基]-苯甲酰胺,2-(2,3,3-三碘-2-丙烯基)-2H-四唑,2-[(1-甲基乙基)磺酰]-5-(三氯甲基)-1,3,4-噻二唑,2-[[6-脱氧-4-O-(4-O-甲基-β-D-吡喃葡糖基)-a-D-吡喃葡糖基]-氨基]-4-甲氧-1H-吡咯并[2,3-d]嘧啶-5-腈,2-氨基丁烷,2-溴-2-(溴甲基)-戊二腈,2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶羧酰胺,2-氯-N-(2,6-二甲基苯基)-N-(异硫代氰酸根合甲基)-乙酰胺,2-苯基苯酚(OPP),3,4-二氯-1-[4-(二氟甲氧)-苯基]-1H-吡咯-2,5-二酮,3,5-二氯-N-[氰基-[(1-甲基-2-丙炔基)-氧]-甲基]-苯甲酰胺,3-(1,1-二甲基丙基-1-氧-1H-茚-2-腈,3-[2-(4-氯苯基)-5-乙氧-3-异噁唑烷基]-吡啶,4-氯-2-氰基-N,N-二甲基-5-(4-甲基苯基)-1H-咪唑-1-磺酰胺,4-甲基-四唑并[1,5-a]喹唑啉-5(4H)-酮,8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二氧杂螺[4,5]癸烷-2-甲胺(methanamine),8-羟喹啉硫酸酯,9H-呫吨-2-[(苯基氨基)-羰基]-9-羧酸酰肼,双-(1-甲基乙基)-3-甲基-4-[(3-甲基苯甲酰)氧]-2,5-噻吩二羧酸酯,顺式-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇,顺式-4-[3-[4-(1,1-二甲基丙基)-苯基-2-甲基丙基]-2,6-二甲基-吗啉氢氯化物,[(4-氯苯基)-偶氮]-氰基乙酸乙酯,碳酸氢钾,甲烷四硫醇钠盐,1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯,N-(2,6-二甲基苯基)-N-(5-异噁唑基羰基)-DL-丙氨酸甲酯,N-(氯乙酰基)-N-(2,6-二甲基苯基)-DL-丙氨酸甲酯,N-(2,3-二氯-4-羟苯基)-1-甲基-环己烷羧酰胺,N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-呋喃基)-乙酰胺N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-噻吩基)-乙酰胺N-(2-氯-4-硝基苯基)-4-甲基-3-硝基-苯磺酰胺,N-(4-环己基苯基)-1,4,5,6-四氢-2-嘧啶胺,N-(4-己基苯基)-1,4,5,6-四氢-2-嘧啶胺,N-(5-氯-2-甲基苯基)-2-甲氧-N-(2-氧代-3-噁唑烷基)-乙酰胺,N-(6-甲氧基)-3-吡啶基)-环丙烷羧酰胺,N-[2,2,2-三氯-1-[(氯乙酰)-氨基]-乙基]-苯甲酰胺,N-[3-氯-4,5-双(2-丙炔基氧)-苯基]-N’-甲氧-甲基酰亚胺酰胺,N-甲酰-N-羟-DL-丙氨酸-钠盐,[2-(二丙基氨基)-2-氧乙基]-乙基硫代磷酰胺O,O-二乙酯,O-甲基S-苯基苯基丙基硫代磷酰胺酯,S-甲基1,2,3-苯并噻二唑-7-硫代羧酸酯,螺[2H]-1-苯并吡喃-2,1,(3’H)-异苯并呋喃]-3’酮,杀细菌剂:溴硝醇,双氯酚,三氯甲基吡啶,福美镍,春雷霉素,辛噻酮,furancarboxylic acid,oxytetracyclin,烯丙苯噻唑,链霉素,叶枯酞,硫酸铜和其他铜制剂。杀虫剂/杀螨剂/杀线虫剂:阿维菌素,乙酰甲胺磷,氟丙菊酯,棉铃威,涕灭威,顺式氯氰菊酯,双甲脒,阿维菌素,AZ 60541,azadirachtin,益棉磷,保棉磷,三唑锡,苏云金杆菌,4-溴-2-(4-氯苯基)-1-(乙氧甲基)-5-(三氟甲基)-1H-吡咯-3-腈,噁虫威,丙硫克百威,杀虫磺,高效氟氯氰菊酯,联苯菊酯,仲丁威,brofenprox,乙基溴硫磷,合杀威,噻嗪酮,丁酮威,butylpyridaben,硫线磷,甲萘威,克百威,三硫磷,丁硫克百威,杀螟丹,chloethocarb,氯氧磷,chlorfenapyr,毒虫畏,氟啶脲,氯甲硫磷,N-[(6-氯-3-吡啶基)-甲基]-N’-氰基-N-甲基-ethanimidamide,毒死稗,甲基毒死稗,顺式苄呋菊酯,clocythrin,四螨嗪,杀螟腈,乙氰菊酯,氟氯氰菊酯,氯氟氰菊酯,三环锡,氯氰菊酯,灭蝇胺,溴氰菊酯,甲基内吸磷,内吸磷,异吸磷,丁醚脲,二嗪磷,除线磷,敌敌畏,dicliphos,百治磷,乙硫磷,除虫脲,乐果,甲基毒虫畏,敌噁磷,乙拌磷,敌瘟磷,emamectin,S-氰戊菊酯,乙硫苯威,乙硫磷,醚菊酯,灭线磷,乙嘧硫磷,苯线磷,喹螨醚,苯丁锡,杀螟硫磷,仲丁威,苯硫威,苯氧威,甲氰菊酯,fenpyrad,唑螨酯,倍硫磷,氰戊菊酯,氟虫腈,氟啶胺,啶稗脲,氟环脲,氟氰戊菊酯,氟虫脲,flufenprox,氟胺氰菊酯,地虫硫磷,安硫磷,噻唑磷,fubfenprox,呋线威,六六六,庚烯磷,氟铃脲,噻螨酮,吡虫啉,异稻瘟净,氯唑磷,异柳磷,异丙威,噁唑磷,伊维菌素,高效氯氟氰菊酯,虱螨脲,马拉硫磷,灭蚜磷,速灭磷,mesulfenphos,四聚乙醛,虫螨畏,甲胺磷,杀扑磷,甲硫威,灭多威,速灭威,milbemectin,久效磷,moxidectin,二溴磷,NC 184,烯啶虫胺,氧乐果,杀线威,亚砜磷,异砜磷,对硫磷,甲基对硫磷,氯菊酯,稻丰散,甲拌磷,伏杀硫磷,亚胺硫磷,磷胺,辛硫磷,抗蚜威,甲基嘧啶磷,嘧啶磷,丙溴磷,猛杀威,丙虫磷,残杀威,丙硫磷,发硫磷,吡蚜酮,吡唑硫磷,哒嗪硫磷,pyresmethrin,除虫菊素,哒螨灵,嘧螨醚,吡丙醚,喹硫磷,蔬果磷,sebufos,氟硅菊酯,治螟磷,硫丙磷,虫酰肼,吡螨胺,tebupirimiphos,氟苯脲,七氟菊酯,双硫磷,特灭威,特丁硫磷,四氯噻吩,thiafenox,硫双威,久效威,甲基乙拌磷,虫线磷,thuringiensin,四溴菊酯,苯螨噻,三唑磷,triazuron,敌百虫,杀铃脲,混杀威,蚜杀多,灭除威,灭杀威,zetamethrin。
还可混合其他已知的活性化合物,如除草剂或肥料和生长调节剂。
活性化合物可以自身或制剂的形式或由此制备的使用形式使用,如即可使用的溶液、悬浮液、可湿性粉剂、糊剂、可溶性粉剂、粉尘和颗粒剂。它们以常规方式使用,例如通过浇灌、喷洒、喷雾、撒布、撒粉、泡沫、刷涂等。还可采用超低容量方法施用或将活性化合物制剂或其自身注射入土壤。也可处理植物种子。
根据本发明的活性化合物用作杀菌剂时,施用量可根据施用的类型在相当宽的范围内变动。在植物部分的处理中,活性化合物的施用量通常为0.1-10000g/ha,优选10-1000g/ha。在种子处理中,活性化合物的施用量通常为0.001-50g/Kg种子,优选0.01-10g/Kg种子。在土壤处理中,活性化合物的施用率通常为0.1-10000g/ha,优选1-5000g/ha。
用于保护工业材料的组合物通常包含1-95%的活性化合物,优选10-75%。
根据本发明的活性化合物的使用浓度取决于要防治的微生物的种类和产地以及要保护的材料的组成。最佳施用率可由试验系列决定。通常使用浓度的范围是基于保护材料重量的0.001-5%,优选0.05-1.0%。
根据本发明用于材料保护的活性化合物和/或组合物、浓缩物或可由此配制的非常广泛的制剂的效力和作用谱可通过在适当时加入其他抗菌活性化合物、杀真菌剂、杀细菌剂、除草剂、杀虫剂或其他活性化合物而增宽作用谱或获得特殊效果,例如额外的对抗害虫的保护。这些混合物比根据本发明的化合物具有更宽的作用谱。制备实施例:实施例1
方法a)
将含有0.6g(0.003摩尔)的2-氟代甲氧基亚氨基-2-(2-羟-苯基)-乙酸甲酯、0.6g(0.003摩尔)的4-(2-氯代苯氧基-5,6-二氟代嘧啶)和0.4g碳酸钾的混合物在20ml乙腈中50℃下搅拌过夜。冷却后,混合物减压浓缩,残留物用乙酸乙酯溶解,并用水洗,过硫酸钠干燥并再在减压下浓缩。残留物用己烷/丙酮(4∶1)过硅胶进行色谱分析。得到0.3g(理论得率的22%)的{2-[6-(2-氯代苯氧基)-5-氟代嘧啶-4-基氧基]-苯基}-氟代甲氧亚氨基-乙酸甲酯,熔点153-155℃。
方法a)
将含有25g(0.111摩尔)的2-氟代甲氧基亚氨基-2-(2-羟苯基)-N-甲基乙酰胺、26.8g(0.111摩尔)的4-(2-氯代苯氧基-5,6-二氟代嘧啶)和18.3g碳酸钾的混合物在300ml乙腈中50℃下搅拌过夜。冷却后,将混合物倒入冰水中并用二氯甲烷萃取两次。合并的有机相经硫酸钠干燥并在减压下浓缩。残留物用己烷/丙酮(7∶3)过硅胶进行色谱分析。得到27.3g(理论得率的55%)的2-{2-[6-(2-氯代苯氧基)-5-氟代嘧啶-4-基氧基]-苯基}-2-氟代甲氧亚氨基-N-甲基乙酰胺,熔点128-129℃。
方法a)
将0.1g 80%浓度的氢化钠悬浮液加入含有0.7g 2-氟代甲氧基亚氨基-2-(2-羟-苯基)-N-甲基乙酰胺和5-苯基-磺酰-3-苯基-<1,2,4>噻二唑的20ml N-甲基吡咯烷酮溶液中,混合物在室温下搅拌过夜。然后将反应混合物减压浓缩,残留物用乙酸乙酯溶解,并用水洗两次,过硫酸钠干燥并再在减压下浓缩。残留物用己烷/丙酮(4∶1)过硅胶进行色谱分析。得到0.6g(理论得率的50%)的2-氟代甲氧亚氨基-N-甲基-2-[2-(3-苯基-[1,2,4]噻二唑-5-基氧基)-苯基]-乙酰胺。logP值:2.9。
式(II)原料的制备
方法b)
将含3.1g(0.01摩尔)2-氟代甲氧基亚氨基-2-[2-(四氢吡喃-2-基氧基)-苯基]-乙酸甲酯的30ml乙酸乙酯溶液用0.2g酸性离子交换树脂处理并在20℃下搅拌过夜(大约16小时)。然后过滤掉离子交换树脂并将滤出液减压浓缩。残留物使用己烷/丙酮(9∶1)过硅胶进行色谱分析。得到0.7g(理论得率的31%)的2-氟代甲氧基亚氨基-2-(2-羟苯基)-乙酸甲酯。logP值:1.6。
方法b1)
将含3.1g(0.01摩尔)2-氟代甲氧基亚氨基-N-甲基-2-[2-(四氢吡喃-2-基氧基)-苯基]-乙酰胺的30ml甲醇溶液用0.1g酸性离子交换树脂处理并在20℃下搅拌过夜(大约16小时)。然后过滤掉离子交换树脂并将滤出液减压浓缩。残留物使用己烷/丙酮(9∶1)过硅胶进行色谱分析。得到0.9g(理论得率的40%)的2-氟代甲氧基亚氨基-2-(2-羟苯基)-N-甲基乙酰胺。logP值:1.1。
式(IX)中间体的制备
实施例(VI-1)
方法c)
在30分钟内,将含75g(0.3摩尔)的[2-(四氢吡喃-2-基氧基)-苯基]-乙酸甲酯和102.9g(0.9摩尔)90%浓度叔丁腈的溶液逐滴加进含39.6g(0.33摩尔)叔丁醇钾的360ml叔丁醇溶液中,反应混合物的温度升至45℃。混合物在室温下搅拌2小时,然后冷却至15℃,并在5-10分钟内逐滴加入51g(0.45摩尔)的溴氟甲烷。不需进一步的冷却,将混合物搅拌过夜,然后用甲基叔丁醚溶解,用水洗,经硫酸钠干燥并减压浓缩。残留物使用己烷/丙酮(9∶1)过硅胶进行色谱分析。得到42.8g(理论得率的45.9%)的2-氟代甲氧基亚氨基-2-[2-(四氢吡喃-2-基氧基)-苯基]-乙酸甲酯油状物。logP值:2.8。
实施例(VI-2)
方法c1)
将甲胺在15分钟内加入含6.2g(0.02摩尔)2-氟代甲氧基亚氨基-2-[2-(四氢吡喃-2基氧基)-苯基]-乙酸甲酯的50ml甲醇溶液,过程中保持冷却。溶液温度不应超过40℃。持续搅拌过夜,然后将混合物减压浓缩。残留物使用己烷/丙酮(7∶3)过硅胶进行色谱分析。得到5.5g(理论得率的88.7%)的2-氟代甲氧基亚氨基-N-甲基-2-[2-(四氢吡喃-2-基氧基)-苯基]-乙酰胺,熔点81℃。
式(III)原料的制备
实施例(III-1)
在0℃将含42.4g(0.45摩尔)苯酚和50.4g(0.45摩尔)叔丁醇钾的400L四氢呋喃溶液逐滴加入含80g(0.6摩尔)4,5,6-三氟嘧啶的1L四氢呋喃溶液中。加料结束后,将反应混合物在0℃搅拌30分钟然后倒入水中并用乙酸乙酯萃取。有机相经硫酸钠干燥,减压浓缩,残留物加入低沸点的石油醚搅拌。得到63.8g(理论得率的68.1%)4-苯氧基-5,6-二氟嘧啶,熔点65-66℃。
前体的制备
为了干燥含609g氟化钾的2.3L环丁砜混合物,将其在145℃和20毫巴下蒸馏,蒸出500ml液体。随后加入1054g5-氯-4,6-二氟嘧啶(DE-A 3843558)和25g四苯基溴化膦,施加5巴的氮气并将混合物在240℃搅拌24小时,压力增加到11巴。将反应混合物冷却至80℃并排出。然后将混合物在大气压下再次缓慢加热并使产物蒸出。当底层温度达到200℃,压力就降低到150毫巴以促进蒸馏和得到更多产物。总共得到664g(理论得率的70.7%)4,5,6-三氟嘧啶,沸点86-87℃。
logP值根据EECDirective 79/831 Annex V.A8用HPLC来测定。(梯度法,乙腈/0.1%含水磷酸)。
使用实施例:
实施例A
单轴霉属实验(葡萄)/保护性
溶剂:47重量份丙酮
乳化剂:3重量份烷基芳基聚乙二醇醚
为了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,浓缩物用水稀释至需要的浓度。
对秧苗喷洒上述施药量的活性化合物制剂来测试保护活性。喷洒涂层干后,用葡萄生单轴霉(Plasmopara viticola)的含水孢子悬浮液对植物接种,然后在大约20℃和100%相对大气湿度的孵育箱中保留1天。随后将植物放在大约21℃和大约90%相对大气湿度的温室中5天。然后将植物弄湿并放在孵育箱中1天。
接种6天后进行评估。0%表示相应于无防治的效力,而100%的效力表示未观察到感染。
在这一实验中,以100g/ha的施药量施用的列于实施例(1),(2),(3),(4),(6),(7),(8),(9),(10),(11),(19),(22),(23),(25),(26),(27),(28)和(29)中的本发明物质具有98%或更高的效力。表A单轴霉实验(葡萄)/保护性表A-(续)单轴霉实验(葡萄)/保护性表A-(续)单轴霉实验(葡萄)/保护性表A-(续)单轴霉实验(葡萄)/保护性表A-(续)单轴霉实验(葡萄)/保护性表A-(续)单轴霉实验(葡萄)/保护性表A-(续)单轴霉实验(葡萄)/保护性
实施例B
黑星菌属实验(苹果)/保护性
溶剂:47重量份丙酮
乳化剂:3重量份烷基芳基聚乙二醇醚
为了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,浓缩物用水稀释至需要的浓度。
对秧苗喷洒上述施药量的活性化合物制剂来测试保护活性。喷洒涂层干后,用苹果黑星病Venturia inaequalis的病原生物体的含水分生孢子悬浮液对植物接种,然后在大约20℃和100%相对大气湿度的孵育箱中保留1天。
随后将植物放在大约21℃和大约90%相对大气湿度的温室中。
接种12天后进行评估。0%表示相当于无防治的效力,而100%的效力表示未观察到感染。
在这一实验中,以10g/ha的施药量施用的列于实施例(1),(2),(3),(4),(5),(6),(7),(9),(11),(19),(22),(23),(25),(26),(28)和(29)中的本发明物质的效力达到99%或更高。表B黑星菌属实验(苹果)/保护性表B-(续)黑星菌属实验(苹果)/保护性表B-(续)黑星菌属实验(苹果)/保护性表B-(续)黑星菌属实验(苹果)/保护性表B-(续)黑星菌属实验(苹果)/保护性表B-(续)黑星菌属实验(苹果)/保护性
实施例C
柄锈菌属实验(小麦)/保护性
溶剂:25重量份N,N-二甲基乙酰胺
乳化剂:0.6重量份烷基芳基聚乙二醇醚
为了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,浓缩物用水稀释至需要的浓度。
对秧苗喷洒上述施药量的活性化合物制剂来测试保护活性。喷洒涂层干后,对植物喷洒隐匿柄锈菌(Puccinia recondita)的分生孢子悬浮液,然后在大约20℃和100%相对大气湿度的孵育箱中保留48小时。
随后将植物放在大约20℃和大约80%相对大气湿度的温室中以促进锈脓庖的发展。
接种10天后进行评估。0%表示相应于无防治的效力,而100%的效力表示未观察到感染。
在这一实验中,以250g/ha的施药量施用的列于实施例(1),(2),(5),(6),(7),(8),(9),(10),(11),(19),(28),(22),(29)和(26)中的本发明物质的效力达到80%或更高。表C柄锈菌属实验(小麦)/保护性表C-(续)柄锈菌属实验(小麦)/保护性表C-(续)柄锈菌属实验(小麦)/保护性表C-(续)柄锈菌属实验(小麦)/保护性表C-(续)柄锈菌属实验(小麦)/保护性
实施例D
柄锈菌实验(小麦)/治疗性的
溶剂:25重量份N,N-二甲基乙酰胺
乳化剂:0.6重量份烷基芳基聚乙二醇醚
为了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,浓缩物用水稀释至需要的浓度。
对秧苗喷洒隐匿柄锈菌的分生孢子悬浮液来测定治疗活性。然后将植物放在20℃和100%相对大气湿度的孵育箱中保留48小时。随后对植物喷洒上述施药量的活性化合物制剂。
将植物放在大约20℃和大约80%相对大气湿度的温室中以促进锈脓庖的发展。
接种10天后进行评估。0%表示相应于无防治的效力,而100%的效力表示未观察到感染。
Claims (13)
2.根据权利要求1所述的式(I)化合物,其中
Q1代表氧或-NH-,
Ar代表任选地单至三取代的苯基或任选地单至四取代的萘基,其中可能的取代基优选选自下列基团:
卤素,氰基,硝基,氨基,羟基,巯基,在所有情况下含1-6个碳原子的直链或支链的烷基、烷氧基、烷基硫基、烷基亚磺酰基或烷基磺酰基,在所有情况下含有2-6个碳原子的直链或支链烯基、烯氧基或炔氧基,在所有情况下含1-6个碳原子和1-13个相同或不同的卤素原子的直链或支链卤代烷基、卤代烷氧基,卤代烷基硫基、卤代烷基亚磺酰基或卤代烷基磺酰基,在所有情况下含2-6个碳原子和1-11个相同或不同的卤素原子的直链或支链卤代烯基或卤代烯氧基,在所有情况下在各个烷基部分含1-6个碳原子的直链或支链的烷基氨基、环烷基氨基、二烷基氨基、烷基羰基或烷基羰基氧基、烷氧基羰基、烷基磺酰基氧基、羟亚氨基烷基或烷氧基亚氨基烷基,在所有情况下含1-6个碳原子并在所有情况下任选被相同或不同取代基单取代或多取代的双重连接的亚烷基或二氧亚烷基,其取代基选自卤素和/或含1-4个碳原子的直链或支链烷基和/或含1-4个碳原子及1-9个相同或不同的卤素原子的直链或支链卤代烷基,在所有情况下含3-7个碳原子并在所有情况下任选被1-4个卤素原子取代的环烷基、环烯基、环烷氧基或环烯氧基,和通过氮原子相连的饱和杂环基,
Q2代表氧或硫,
X代表氢、氟、氯或溴和
L1,L2,L3和L4是相同或不同的并彼此独立地代表氢、卤素、氰基、硝基,代表在所有情况下含1-6个碳原子并在所有情况下任选被1-5个卤素原子取代的烷基、烷氧基、烷基硫基、烷基亚磺酰基或烷基磺酰基。
3.根据权利要求1所述的式(I)化合物,其中
Q1代表氧或-NH-,
Ar代表被相同或不同取代基任选地单取代或二取代的苯基,其中可能的取代基优选选自下列基团:
氟,氯,溴,氰基,硝基,甲基,乙基,正或异丙基,正-、异-、仲-或叔-丁基,丙烯基,丁-3-烯-2-基,2-甲基丙烯基,环丙基,甲氧基,乙氧基,正或异丙氧基,烯丙氧基,甲硫基,乙硫基,正或异丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,二氟氯甲氧基,三氟乙氧基,二氟甲硫基,三氟甲硫基,二氟氯甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲氧基羰基,乙氧基羰基,甲氧亚胺基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基,乙氧亚氨基乙基,在所有情况下双重连接的亚丙基、亚丁基或亚戊基,或在所有情况下双重连接的亚甲二氧基或亚乙二氧基,并且均可被相同或不同的取代基任选地单取代至四取代,取代基选自氟、氯、甲基、三氟甲基和乙基,
Q2代表氧或硫,
X代表氢、氟或氯及
L1,L2,L3和L4是相同或不同的并彼此独立地代表氢、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、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基、三氟甲基、三氟乙基、二氟甲氧基、三氟甲氧基、二氟氯甲氧基、三氟乙氧基、二氟甲硫基、二氟氯甲硫基、三氟甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基。
4.根据权利要求1所述的通式(I)化合物,其中
Q1代表氧或-NH-,
其中
Ar代表任选被相同或不同的取代基单取代或二取代的苯基,其中可能的取代基优选选自下列:
氟,氯,溴,氰基,硝基,甲基,乙基,正或异丙基,正-、异-、仲-或叔-丁基,丁-3-烯-2-基,2-甲基丙烯基,环丙基,甲氧基,乙氧基,正或异丙氧基,烯丙氧基,甲硫基,乙硫基,正或异丙硫基,三氟甲基,三氟乙基,二氟甲氧基,三氟甲氧基,三氟乙氧基,二氟甲硫基,三氟甲硫基,甲氧基羰基,乙氧基羰基,甲氧亚胺基甲基,乙氧亚氨基甲基,甲氧亚氨基乙基,乙氧亚氨基乙基,在所有情况下双重连接的亚丙基,亚丁基或亚戊基,或在所有情况下双重连接的亚甲二氧基或亚乙二氧基,并且均可被相同或不同的取代基任选单取代至四取代,取代基选自氟、氯、甲基、三氟甲基和乙基,
Q2代表氧或硫,
X代表氢、氟或氯及
L1和L3可以是相同或不同的并彼此独立地代表氢或甲基和
L2和L4代表氢。
5.根据权利要求1所述的式(I)化合物,其中Q1代表-NH-。
6.组合物,其特征在于包括至少一种如权利要求1所述的式(I)化合物。
7.防治害虫的方法,其特征在于对害虫和/或其栖息地使用如权利要求1所述的式(I)化合物。
8.根据权利要求1-6中任一项所述的式(I)化合物或组合物防治害虫的用途。
9.制备农药的方法,其特征在于将根据权利要求1-5中任一项所述的式(I)化合物与填充剂和/或表面活性剂混合。
12.制备如权利要求11定义的式(II)化合物的方法,其特征在于(方法b)水解式(IX)的缩醛
其中
R1代表烷基,
R2代表氢或烷基或
R1和R2与它们相连的原子一起代表一个五元或六元杂环并且
Q1,L1,L2,L3和L4均如上所述,
适当时在稀释剂的存在下和适当时在酸的存在下,温度为-20℃-120℃,优选温度-10℃-80℃,或(方法b1)其中Q1是氧的式(II)羟芳基化合物与甲胺反应,适当时在稀释剂的存在下。
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DE19611653A1 (de) * | 1995-10-18 | 1997-04-24 | Bayer Ag | Fluormethoxyacrylsäurederivate |
DE19723195A1 (de) | 1997-06-03 | 1998-12-10 | Bayer Ag | Fluormethoximinoverbindungen |
-
1997
- 1997-06-03 DE DE19723195A patent/DE19723195A1/de not_active Withdrawn
-
1998
- 1998-05-22 BR BR9810407-1A patent/BR9810407A/pt not_active Application Discontinuation
- 1998-05-22 JP JP50140999A patent/JP2002502397A/ja active Pending
- 1998-05-22 PL PL98337190A patent/PL337190A1/xx unknown
- 1998-05-22 AU AU80199/98A patent/AU8019998A/en not_active Abandoned
- 1998-05-22 WO PCT/EP1998/003038 patent/WO1998055461A1/de not_active Application Discontinuation
- 1998-05-22 KR KR1019997010734A patent/KR20010012772A/ko not_active Application Discontinuation
- 1998-05-22 US US09/445,084 patent/US6306855B1/en not_active Expired - Fee Related
- 1998-05-22 CN CN98805658A patent/CN1258284A/zh active Pending
- 1998-05-22 EP EP98928311A patent/EP0986542A1/de not_active Withdrawn
- 1998-05-22 ID IDW991453A patent/ID22983A/id unknown
-
2001
- 2001-08-20 US US09/933,208 patent/US6632817B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
AU8019998A (en) | 1998-12-21 |
US20020028811A1 (en) | 2002-03-07 |
PL337190A1 (en) | 2000-08-14 |
ID22983A (id) | 1999-12-23 |
KR20010012772A (ko) | 2001-02-26 |
US6632817B2 (en) | 2003-10-14 |
BR9810407A (pt) | 2000-08-22 |
US6306855B1 (en) | 2001-10-23 |
JP2002502397A (ja) | 2002-01-22 |
DE19723195A1 (de) | 1998-12-10 |
WO1998055461A1 (de) | 1998-12-10 |
EP0986542A1 (de) | 2000-03-22 |
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