CN101239955A - 制备杀真菌组合物的方法 - Google Patents
制备杀真菌组合物的方法 Download PDFInfo
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- CN101239955A CN101239955A CNA2008100032878A CN200810003287A CN101239955A CN 101239955 A CN101239955 A CN 101239955A CN A2008100032878 A CNA2008100032878 A CN A2008100032878A CN 200810003287 A CN200810003287 A CN 200810003287A CN 101239955 A CN101239955 A CN 101239955A
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- Prior art keywords
- alkyl
- halogen
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- optional
- carbon atom
- Prior art date
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- 230000000855 fungicidal effect Effects 0.000 title abstract description 5
- 239000000417 fungicide Substances 0.000 title abstract description 4
- 239000000203 mixture Substances 0.000 title description 39
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000001301 oxygen Substances 0.000 claims abstract description 32
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 32
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 125000001118 alkylidene group Chemical group 0.000 claims abstract description 5
- -1 sulphinyl Chemical group 0.000 claims description 123
- 150000001875 compounds Chemical class 0.000 claims description 69
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 56
- 229910052799 carbon Inorganic materials 0.000 claims description 44
- 150000001721 carbon Chemical group 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 150000002367 halogens Chemical class 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 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
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 239000005864 Sulphur Chemical group 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 125000003368 amide group Chemical group 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical group O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 150000001345 alkine derivatives Chemical class 0.000 claims description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 3
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 31
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 abstract 1
- 150000001925 cycloalkenes Chemical class 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- 238000002360 preparation method Methods 0.000 description 36
- 239000011737 fluorine Substances 0.000 description 32
- 229910052731 fluorine Inorganic materials 0.000 description 32
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 30
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- 239000000460 chlorine Substances 0.000 description 30
- 229910052801 chlorine Inorganic materials 0.000 description 30
- 239000002994 raw material Substances 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 241000894006 Bacteria Species 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 150000004885 piperazines Chemical class 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 16
- 229910052794 bromium Inorganic materials 0.000 description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- 150000003851 azoles Chemical class 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 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 12
- 239000002253 acid Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 241000196324 Embryophyta Species 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 235000015320 potassium carbonate Nutrition 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 7
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 7
- 235000011118 potassium hydroxide Nutrition 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical class CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 235000013339 cereals Nutrition 0.000 description 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 235000007516 Chrysanthemum Nutrition 0.000 description 5
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
- 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 5
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 5
- 229940031815 mycocide Drugs 0.000 description 5
- 229960001866 silicon dioxide Drugs 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 5
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
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- 241000233614 Phytophthora Species 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
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- 238000010521 absorption reaction Methods 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
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- 238000004821 distillation Methods 0.000 description 4
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 4
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 4
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
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- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 3
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- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 3
- 241000228437 Cochliobolus Species 0.000 description 3
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- 229910052802 copper Inorganic materials 0.000 description 3
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- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
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- 239000000463 material Substances 0.000 description 3
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- 229960003424 phenylacetic acid Drugs 0.000 description 3
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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- 239000012312 sodium hydride Substances 0.000 description 3
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- 238000001228 spectrum Methods 0.000 description 3
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- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 description 1
- 229960000611 pyrimethamine Drugs 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- ITKAIUGKVKDENI-UHFFFAOYSA-N pyrimidifen Chemical compound CC1=C(C)C(CCOCC)=CC=C1OCCNC1=NC=NC(CC)=C1Cl ITKAIUGKVKDENI-UHFFFAOYSA-N 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 229930185107 quinolinone Natural products 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- MSHXTAQSSIEBQS-UHFFFAOYSA-N s-[3-carbamoylsulfanyl-2-(dimethylamino)propyl] carbamothioate;hydron;chloride Chemical compound [Cl-].NC(=O)SCC([NH+](C)C)CSC(N)=O MSHXTAQSSIEBQS-UHFFFAOYSA-N 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- 229940063650 terramycin Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 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
- 229930192474 thiophene Natural products 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
- 108010067167 thuricin Proteins 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-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
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 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
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003751 zinc Chemical class 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
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
-
- 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
- A01N43/88—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 six-membered rings with three ring hetero atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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Abstract
本发明涉及式(I)的新的氮杂二氧杂环烯及其制法和作为杀真菌剂的应用,式Ⅰ其中A代表任选取代的烷二基(亚烷基);A代表各自任选取代的亚芳基或亚杂芳基;E代表选自(a)、(b)、(c)、(d)和(e)的基团;其中,Y代表氧、硫、亚甲基(CH2)或烷氨基(N-R);和Z-G代表各种取代基。
Description
本申请是申请号为200510125024.0、申请日为1994年7月29日、发明名称为“制备杀真菌组合物的方法”的发明专利申请的分案申请,其原始母案的申请号为94193669.4(PCT/EP94/02533)。
本发明涉及新的取代氮杂二氧杂环烯、其制备方法以及其作为杀真菌剂的用途。
业已公开某些取代的5,6-二氢-1,4,2-二嗪具有杀真菌特性(参见,JP-A 01221371-引述于Chem.Abstracts 112:98566t;JP-A 02001484-引述于Chem.Abstracts 113:6381y)。
然而,这些化合物并未得到特别的重视。
现已发现通式(I)的新的取代的氮杂二氧杂环烯
其中
A代表任选取代的烷二基(亚烷基),
Ar各自任选取代的亚芳基或亚杂芳基;
E代表在2位上带R1基的1-烯-1,1-二基,或在2位上带R2基的2-氮杂-1-烯-1,1-二基,或在1位上带R1基的3-氧杂或3-硫杂-1-丙烯-2,3-二基,或代表在3位上带R基和在1位上带R1基的3-氮杂-1-丙烯-2,3-二基,或代表在1位上带R2基的1-氮杂-1-丙烯-2,3-二基,或代表在1位上带R2基的3-氧杂或3-硫杂-1-氮杂-丙烯-2,3-二基,或代表在3位上带R基和在1位上带R基的1,3-二氮杂-1-丙烯-2,3-二基,或代表任选取代的亚氨基(“氮杂亚甲基’,N-R3),
其中
R代表烷基,
R1代表氢、卤素、氰基或各自任选取代的烷基、烷氧基、烷硫基、烷氨基或二烷基氨基,
R2代表氢、氨基、氰基或各自任选取代的烷基、烷氧基、烷氨基或二烷基氨基;和
R3代表氢、氰基或各自任选取代的烷基、链烯基、炔基、环烷基或环烷基烷基,
G代表一个单键、氧、或代表各自任选由卤素、羟基、烷基、卤代烷基或环烷基取代的烷二基、链烯二基、氧杂链烯二基、炔二基,或代表下列基团之一:
-Q-CQ-,-CQ-Q-,-CH2-Q-,-Q-CH2-,-CQ-Q-CH2-,
-CH2-Q-CQ-,-Q-CQ-CH2-,-Q-CQ-Q-CH2-,-N=N-,-S(O)n-,
-CH2-S(O)n-,-CQ-,-S(O)n-CH2-,-C(R4)=N-O-,
-C(R4)=N-O-CH2-,-N(R5)-,-CQ-N(R5)-,-N(R5)-CQ-,
-Q-CQ-N(R5)-,-N=C(R4)-Q-CH2-,-CH2-O-N=C(R4)-,
-N(R5)-CQ-Q-,-CQ-N(R5)-CQ-Q-,-N(R5)-CQ-Q-CH2-,
-CQ-CH2-或-N=N-C(R4)=N-O-,
其中
n代表0、1或2的数字;
Q代表氧或硫;
R4代表氢、氰基或代表各自任选取代的烷基、烷氧基、烷硫基、烷氨基、二烷基氨基或环烷基,和
R5代表氢、羟基、氰基或代表各自任选取代的烷基、烷氧基或环烷基,和
Z代表 各自任选取代的烷基、链烯基、炔基、环烷基、芳基或杂环基。
还业已发现,可以如下获得通式(I)的新的取代的氮杂二氧杂环烯:
(a)第一步,适宜时,在酸受体存在下和适宜时,在稀释剂存在下,使通式(II)的羧酸衍生物与羟基胺或与其卤化氢化物反应,
其中
Ar、E、G和Z具有上述含意,和
R代表烷基;
且第一步的产物在原位,即无需中间分离,在第二步中,适宜时,在酸受体存在下,和适宜时,在稀释剂存在下,与通式(III)的二取代烷反应,
X-A-X(III)
其中
A具有上述含意,且
X代表卤素、烷基磺酰氧基或芳基磺酰氧基,或(b)当式(I)中,G代表氧或-CH2-O-基团,且A、Ar、E和
Z具有上述含意时;
适宜时,在酸受体存在下,且适宜时,在稀释剂存在下,使通式(IV)的羟基芳基化合物与通式(V)的化合物反应,
其中
A、Ar和E具有上述含意;
Z-(CH2)m-X(V)
其中
X和Z具有上述含意,且
m代表数字0或1;
且适宜时,随后对Z基团通过常规方法进行取代反应,或(c)当式(I)中,G代表-Q-CH2-基团,和A、Ar、E和Z基
团具有上述含意时,
适宜时在酸受体存在下,并且适宜时在稀释剂存在下,使通式(VI)的卤代甲基化合物与通式(VII)的化合物反应,
其中
A、Ar和E具有上述含意,且
X1代表卤素,
Z-Q-H (VII)
其中
Q和Z具有上述含意,或
(d)适宜时在稀释剂存在下,使通式(VIII)的羟基烷氧基酰胺与脱水剂进行环化反应,
其中
A、Ar、E、G和Z具有上述含意。
最后还发现,通式(I)的新的取代的氮杂二氧杂环烯具有非常高的杀真菌活性。
当适宜时,本发明的化合物可以以各种可能的异构体,特别是E和Z异构体的混合物形式存在。所要求保护的是E和Z异构体及其异构体的任何混合物。
本发明优选这样的式(I)化合物,其中
A代表具有1至3个碳原子的烷二基,它任选由卤素或1至4个碳原子的烷基或卤代烷基取代;
Ar代表各自任选取代的亚苯基或亚萘基,或代表5或6个环原子的、且其中至少一个环原子代表氧、硫或氮,适宜时另外的一或两个环原子代表氮的亚杂芳基,其中可能的取代基优选选自:
卤素、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、各自为直链或支链的烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,它们各有1至6个碳原子,各自为直链或支链的链烯基、链烯氧基或炔氧基,它们各有2至6个碳原子,各自为直链或支链的卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基,它们各有1至6个碳原子和1至13个相同或不同的卤原子,各自为直链或支链的卤代链烯基或卤代链烯氧基,它们各有2至6个碳原子和1至13个相同或不同的卤原子,各自为直链或支链的烷基氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷氧羰基、烷基磺酰氧基、羟基亚氨基烷基或烷氧基亚氨基烷基,它们各在各自烷基部分有1至6个碳原子,或代表各自为二价的亚烷基或二氧亚烷基,它们各有1至6个碳原子且各自任选由相同或不同的选自卤素和/或1至4个碳原子的直链或支链烷基和/或含1至4个碳原子和1至9个相同或不同卤原子的直链或支链卤代烷基的取代基单取代或多取代;
E代表下列基团之一:
其中
Y代表氧、硫、亚甲基(CH2)或烷基亚氨基(N-R),
R代表具有1至6个碳原子的烷基,
R1代表氢、卤素、氰基、或代表烷基、烷氧基、烷硫基、烷氨基或二烷基氨基,它们各在烷基上有1至6个碳原子且各自任选由卤素、氰基或C1-C4烷氧基取代,
R2代表氢、氨基、氰基,或代表烷基、烷氧基、烷氨基或二烷基氨基,它们各自在烷基部分上有1至6个碳原子且各自任选地由卤素、氰基或C1-C4烷氧基取代,和
R3代表氢、氰基,或代表烷基、链烯基或炔基,它们有最多6个碳原子并任选由卤素、氰基或C1-C4烷氧基取代,或代表在环烷基部分有3至6个碳原子和如果适宜在烷基部分有1至4个碳原子的环烷基或环烷基烷基,它们各自任选由卤素、氰基、羧基、C1-C4烷基或C1-C4烷氧羰基取代,
G代表单键、氧,或代表烷二基、链烯二基、氧杂烯二基、炔二基,它们各自有最多4个碳原子且各自任选由卤素、羟基、C1-C4烷基、C1-C4卤代烷基或C3-C6环烷基取代,或代表下列基团之一:
-Q-CQ-,-CQ-Q-,-CH2-Q-,-Q-CH2-,-CQ-Q-CH2-,
-CH2-Q-CQ-,-Q-CQ-CH2-,-Q-CQ-Q-CH2-,-N=N-,-S(O)n-,
-CH2-S(O)n-,-CQ-,-S(O)n-CH2-,-C(R4)=N-O-,
-C(R4)=N-O-CH2-,-N(R5)-,-CQ-N(R5)-,-N(R5)-CQ-,
-Q-CQ-N(R5)-,-N=C(R4)-Q-CH2-,-CH2-O-N=C(R4)-,
-N(R5)-CQ-Q-,-CQ-N(R5)-CQ-Q-,-N(R5)-CQ-Q-CH2-,
-CQ-CH2-或-N=N-C(R4)=N-O-,
其中
n代表数字0、1和2,
Q代表氧或硫,
R4代表氢、氰基,或代表烷基、烷氧基、烷硫基、烷氨基或二烷基氨基,它们各在烷基上有1至6个碳原子且各自任选由卤素、氰基或C1-C4烷氧基取代,或代表有3至6个碳原子的环烷基,它们任选由卤素、氰基、羧基、C1-C4烷基或C1-C4烷氧羰基取代,和
R5代表氢、羟基、氰基,或代表任选由卤素、氰基或C1-C4烷氧基取代的1至6个碳原子的烷基,或代表任选由卤素、氰基、羧基、C1-C4烷基或C1-C4烷氧羰基取代的3至6个碳原子的环烷基,和
Z代表1至8个碳原子的烷基,它任选由卤素、氰基、羟基、氨基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基(各自可任选由卤素取代)取代,或代表链烯基或炔基,它们含最多8个碳原子并各自任选由卤素取代,或代表3至6个碳原子的环烷基,它们任选由卤素、氰基、羧基、苯基(任选由卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基取代)、C1-C4烷基或C1-C4烷氧羰基取代,或代表各自任选取代的苯基、萘基或(任选苯稠合的)具5或6个环原子的杂环基,环原子中至少一个代表氧、硫或氮,并且如果适宜,另有一或两个环原子代表氮,其中可能的取代基优选选自:氧(代替两个孪位氢原子)、卤素、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、各自为直链或支链的烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,它们各有1至6个碳原子,各自为直链或支链的链烯基或链烯氧基,它们各有2至6个碳原子,各自为直链或支链的卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基,它们各有1至6个碳原子和1至13个相同或不同的卤原子,各自为直链或支链的卤代链烯基、卤代链烯氧基,它们各有2至6个碳原子和1至13个相同或不同的卤原子,各自为直链或支链的烷氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷氧羰基、烷基磺酰氧基、羟亚氨基烷基或烷氧基亚氨基烷基,它们在各自烷基部分有1至6个碳原子,各自为二价的亚烷基或二氧亚烷基,它们各有1至6个碳原子且各自任选由选自卤素和/或1至4个碳原子的直链或支链烷基和/或含1至4个碳原子和1至9个相同或不同的卤原子的直链或支链卤代烷基的相同或不同的取代基单取代或多取代,或3至6个碳的环烷基,杂环基或杂环基甲基,它们各有3至7个环原子,其中各有1至3个环原子是相同或不同的杂原子——特别是氮、氧和/或硫,和苯基、苯氧基、苄基、苄氧、苯乙基或苯乙氧基,它们在苯基部分任选由选自卤素、氰基、硝基、羧基、氨基甲酰基和/或1至4个碳原子的直链或支链烷基和/或含1至4个碳原子和1至9个相同或不同的卤原子的直链或支链卤代烷基和/或含1至4个碳原子的直链或支链烷氧基和/或含1至4个碳原子和1至9个相同或不同的卤原子的直链或支链卤代烷氧基和/或各自含最多5个碳原子的烷基羰基或烷氧羰基的相同或不同的取代基单取代或多取代。
在定义中,饱和或不饱和烃链,如烷基、烷二基、链烯基或炔基,及连有杂原子的情况,如在烷氧基,烷硫基或烷氨基中,在所有情况下各自是直链或支链。
卤素通常代表氟、氯、溴或碘,优选氟、氯或溴,特别是氟或氯。
具体地说,本发明涉及式(I)的化合物,其中
A代表亚甲基或二亚甲基(乙-1,2-二基),它们可任选由氟、氯、甲基、乙基或三氟甲基取代,
Ar代表各自任选取代的邻、间或对亚苯基,或代表呋喃二基、噻吩二基、吡咯二基、吡唑二基、三唑二基、唑二基、异唑二基、噻唑二基、异噻唑二基、二唑二基、噻二唑二基、吡啶二基、嘧啶二基、哒嗪二基、吡嗪二基、1,3,4-三嗪二基或1,2,3-三嗪二基,其中可能的取代基特别是选自:
氟、氯、氰基、甲基、乙基、三氟甲基、甲氧基、乙氧基、甲硫基、甲基亚磺酰基或甲基磺酰基,
E代表下列基团之一:
其中
Y代表氧、硫、亚甲基(CH2)或烷基亚氨基(N-R),
R代表甲基、乙基、正或异丙基,或正、异或叔丁基,
R1代表氢、氟、氯、溴、氰基、或代表甲基、乙基、丙基、甲氧基、乙氧基、甲硫基、乙硫基、甲氨基、乙氨基或二甲基氨基,它们任选由氟、氯、氰基、甲氧基或乙氧基取代;
R2代表氢、氨基、氰基,或代表甲基、乙基、甲氧基、乙氧基、甲氨基、乙氨基或二甲基氨基,它们各自任选由氟、氯、氰基、甲氧基或乙氧基取代,和
R3代表氢、氰基,或代表甲基、乙基、正或异丙基、正、异或叔丁基,它们各自任选由氟、氰基、甲氧基或乙氧基取代,或代表烯丙基或炔丙基,或代表环丙基、环丁基、环戊基、环己基、环丙基甲基、环丁基甲基、环戊基甲基、或环己基甲基,它们各自任选由氟、氯、氰基、羧基、甲基、乙基、正或异丙基、甲氧羰基或乙氧羰基取代,
G代表单键、氧、或代表亚甲基、二亚甲基(乙-1,2-二基)、乙烯-1,2-二基、乙炔-1,2-二基,它们各自任选由氟、氯、羟基、甲基、乙基、正或异丙基、三氟甲基、环丙基、环丁基、环戊基或环己基取代,或代表下列基团之一:
-Q-CQ-,-CQ-Q-,-CH2-Q-,-Q-CH2-,-CQ-Q-CH2-,
-CH2-Q-CQ-,-Q-CQ-CH2-,-Q-CQ-Q-CH2-,-N=N-,-S(O)n-,
-CH2-S(O)n-,-CQ-,-S(O)n-CH2-,-C(R4)=N-O-,
-C(R4)=N-O-CH2-,-N(R5)-,-CQ-N(R5)-,-N(R5)-CQ-,
-Q-CQ-N(R5)-,-N=C(R4)-Q-CH2-,-CH2-O-N=C(R4)-,
-N(R5)-CQ-Q-,-CQ-N(R5)-CQ-Q-或-N(R5)-CQ-Q-CH2-,
其中
n代表数字0、1或2,
Q代表氧或硫,
R4代表氢、氰基、或代表甲基、乙基、正或异丙基、正、异或叔丁基、甲氧基、乙氧基、丙氧基、丁氧基、甲硫基、乙硫基、丙硫基、丁硫基、甲氨基、乙氨基、丙氨基、二甲基氨基或二乙基氨基,它们各自任选由氟、氯、氰基、甲氧基或乙氧基取代,或代表环丙基、环丁基、环戊基或环己基,它们各自任选由氟、氯、氰基、羧基、甲基、乙基、正或异丙基、甲氧羰基或乙氧羰基取代,和
R5代表氢、羟基、氰基、或代表甲基、乙基、正或异丙基、正、异、仲或叔丁基,它们各自任选由氟、氯、氰基、甲氧基或乙氧基取代,或代表环丙基、环丁基、环戊基或环己基,它们各自任选由氟、氯、氰基、羧基、甲基、乙基、正或异丙基、甲氧羰基或乙氧羰基取代,和
Z代表甲基、乙基、正或异丙基、或正、异、仲、或叔丁基,它们各自任选由氟、氯、溴、氰基、羟基、氨基、甲氧基、乙氧基、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(它们各自任选由氟和/或氯取代)取代,或代表烯丙基、丁烯基、1-甲基-烯丙基、炔丙基或1-甲基-炔丙基,它们各自任选由氟、氯或溴取代,或代表环丙基、环丁基、环戊基或环己基,它们各自任选由氟、氯、溴、氰基、羧基、苯基(任选由氟、氯、溴、氰基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、三氟甲基、甲氧基、乙氧基、正或异丙氧基、二氟甲氧基或三氟甲氧基取代)、甲基、乙基、正或异丙基、甲氧羰基或乙氧羰基取代,或代表各自任选被取代的苯基、萘基、呋喃基、四氢呋喃基、苯并呋喃基、四氢吡喃基、噻吩基、苯并噻吩基、吡咯基、二氢吡咯基、四氢吡咯基、苯并吡咯基、苯并二氢吡咯基、唑基、苯并唑基、异唑基、噻唑基、苯并噻吩基、异噻唑基、咪唑基、苯并咪唑基、二唑基、噻二唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基或1,3,5-三嗪基,其中可能的取代基优选选自:氧(替代二个孪位氢原子)、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、二氟甲氧基、三氟甲氧基、二氟甲硫基、三氟甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基、甲氨基、乙氨基、正或异丙氨基、二甲基氨基、二乙基氨基、乙酰基、丙酰基、乙酰氧基、甲氧羰基、乙氧羰基、甲磺酰氧基、乙磺酰氧基、羟亚氨基甲基、羟亚氨基乙基、甲氧基亚氨基甲基、乙氧基亚氨基甲基、甲氧基亚氨基乙基或乙氧基亚氨基乙基;或三亚甲基(丙-1,3-二基)、亚甲二氧基或亚乙二氧基、环丙基、环丁基、环戊基或环己基,它们各自任选被选自氟、氯、甲基、乙基或正或异丙基的相同或不同的取代基单取代或多取代,以及苯基、苯氧基、苄基或苄氧基,它们各在苯基部分任选被选自氟、氯、溴、氰基、硝基、羧基、氨基甲酰基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、三氟甲基、甲氧基、乙氧基、正或异丙氧基、二氟甲氧基、三氟甲氧基、乙酰基、甲氧羰基或乙氧羰基的相同或不同的取代基单取代或多取代。最优选的一组本发明化合物是这样的式(I)化合物,其中
A代表二亚甲基(乙-1,2-二基),
Ar代表邻-亚苯基,吡啶-2,3-二基或噻吩-2,3-二基,
E代表下列基团之一:
其中
R1和R2各自代表甲氧基,
G代表氧,亚甲基或下列基团之一:
-CH2-O-,-O-CH2-,-S(O)n-,-CH2-S(O)n-,-S(O)n-CH2-,
-C(R4)=N-O-,-O-N=C(R4)-,-C(R4)=N-O-CH2-,-N(R5)-或
-CH2-O-N=C(R4)-,
其中
n代表数字0,1或2,
R4代表氢,甲基或乙基,和
R5代表氢,甲基或乙基,和
Z代表各自任选被取代的苯基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基或1,3,5-三嗪基,其中可能的取代基优选选自:
氟、氯、溴、氰基、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、正或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基或乙磺酰基、三氟甲基、二氟甲氧基、三氟甲氧基、二氟甲硫基、三氟甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基、甲氧羰基、乙氧羰基、甲氧基亚氨基乙基、乙氧基亚氨基乙基、甲氧基亚氨基乙基或乙氧基亚氨基乙基,或亚甲二氧基或亚乙二氧基,它们各自任选由选自氟、氯、甲基或乙基的相同或不同的取代基单取代或双取代,以及苯基、苯氧基、苄基或苄氧基,它们各自在苯基部分任选由选自氟、氯、溴、氰基、甲基、乙基、正或异丙基、正、异、仲或叔丁基、三氟甲基、甲氧基、乙氧基、正或异丙氧基、二氟甲氧基或三氟甲氧基的相同或不同的取代基单取代或多取代。
上述的一般基团定义或优选范围的基团定义适用于式(I)的终产物,而且也适用于在所有情况下制备所需的原料或中间体。
如果需要这些基团的定义可以相互组合,这就是说,所指明的优选化合物范围间的组合也是可能的。
例如,如果用α-甲氧基亚氨基-α-(2-苯氧基苯基)-乙酸甲酯、羟胺盐酸盐和1,2-二溴乙烷作原料,本发明制备方法(a)中的反应途径可以用下列反应式概述:
例如,如果用3-[α-甲氧基亚氨基-α-(2-羟基-苯基)-甲基]-5,6-二氢-1,4,2-二嗪和苯甲基氯作原料,本发明制备方法(b)中的反应途径可以用下列反应式概述:
例如,如果用3-[α-甲氧基亚氨基-α-(2-氯甲基-苯基)-甲基]-5,6-二氢-1,4,2-二嗪和2-甲基苯酚作原料,本发明制备方法(c)中的反应途径可以用下列反应式概述:
例如,如果用N-(2-羟基-乙氧基)-α-甲氧基亚氨基-α-(2-苯氧基-苯基)-乙酰胺作原料,本发明的制备方法中的反应途径可以用下列反应式概述:
式(II)提供需要用作进行本发明方法(a)的原料的羧酸衍生物的一般定义。在式(II)中,Ar,E,G和Z优选或特别是具有与本发明式(I)化合物描述有关的业已提到的优选或特别优选的Ar,E,G和Z含义;R优选代表1至4个碳原子的烷基;特别是甲基或乙基。
式(II)的原料是已知和/或可以由本身已知的方法制备(参见,EP-A 178826,EP-A 242081,EP-A 382375,EP-A 493711)。
式(III)提供其他的在本发明方法(a)中用作原料的二取代烷的一般性定义。式(III)中,A优选或特别是具有与本发明式(I)化合物描述有关的业已提到的优选或特别优选的A的含义;X优选代表氯、溴、甲磺酰氧基、苯磺酰氧基或甲苯磺酰氧基。
式(III)的原料是已知的有机合成化合物。
式(IV)提供在制备通式(I)化合物的本发明方法(a)中用作原料的羟基芳基化合物的一般性定义。式(IV)中,A,Ar和E优选或特别是具有与式(I)化合物的描述有关的业已给出的优选或特别优选的A,Ar和E的那些含意。
式(IV)的原料迄今尚未见于文献,作为新物质,它为本申请的一部分。
式(IV)的新羟基芳基化合物可按如下获得:适宜时,在稀释剂存在下,例如在水,甲醇,乙醇或乙酸乙酯存在下,在0℃至100℃间,使通式(IX)的四氢吡喃氧基化合物与酸反应,例如盐酸,硫酸,甲磺酸,苯磺酸,对甲苯磺酸,或与酸性离子交换剂反应(参见制备实施例)。
其中
A,Ar和E具有上述含意。
式(IX)的四氢吡喃氧基化合物迄今尚未见于文献,作为新物质,它为本申请的一部分。
式(IX)的新四氢吡喃氧基化合物可按如下获得:适宜时,在酸受体如氢氧化钾存在下,且适宜时,在稀释剂如甲醇和水存在下,使通式(X)的酯与羟基胺反应(或如果适宜,与其盐酸盐反应),并且适宜时,在酸受体例如碳酸钾存在下,在0℃-100℃间使形成的中间体再原位与上述的通式(III)的二卤代烷反应,(参见,根据本发明方法(a)和制备实施例的描述),
其中
Ar,E和R具有上述含意。
式(X)的酯迄今尚未见于文献,作为新物质,它为本申请的一部分。
式(X)的新酯可如下获得:将通式(XI)的四氢吡喃基氧基-苯基乙酸酯用常规方法衍化(参见制备实施例):
其中
Ar和R具有上述含意。
式(XI)的四氢吡喃基氧基-苯基乙酸酯迄今尚未见于文献,作为新物质,它为本申请的一部分。
式(XI)的新的四氢吡喃氧基-苯基乙酸酯可如下获得:适宜时,在催化剂如对亚甲苯磺酸存在下,和适宜时在稀释剂如四氢呋喃存在下,在0℃至100℃间使通式(XII)的羟基苯基乙酸酯与二氢吡喃反应,
其中
Ar和R具有上述含意;(参见制备实施例)。
式(XII)的原料为已知的合成化合物。
式(V)提供另外的用作在制备通式(I)化合物的本发明方法(b)中用作原料的化合物的一般性定义。式(V)中,Z优选或特别是具有与式(I)化合物描述有关的业已提到的优选或特别优选的Z的含义;X优选代表氯,溴,甲磺酰氧基,苯磺酰氧基或甲苯磺酰氧基。
式(V)的原料是已知的合成化合物。
式(VI)提供在制备通式(I)化合物的本发明方法(c)中用作原料的卤代甲基化合物的一般性定义。式(VI)中,A,Ar和E优选或特别是具有与式(I)化合物描述相关的业已提到的优选,或特别优选的A,Ar和E的那些含意;X1优选代表氟,氯,溴或碘,特别是氯或溴。
式(VI)的原料迄今尚未见于文献,作为新物质,它为本申请的一部分。
式(VI)的新卤代甲基化合物可如下获得:适宜时,在催化剂如2,2’-偶氮异丁腈存在下,且如果适宜在稀释剂如四氯甲烷存在下,在0~150℃使通式(XIII)的甲基化合物与卤化剂例如N-溴或N-氯-琥珀酰亚胺反应(参见制备实施例),
式中
A,Ar和E具有上述含意。
需作为前体的式(XIII)甲基化合物迄今尚未见于文献;作为新物质,它为本申请的一部分。
式(XIII)的新的甲基化合物可如下获得:适宜时,在酸受体如氢氧化钾存在下,且如果适宜,在稀释剂如甲醇存在下,使式(XIV)的酯与羟胺或羟胺盐酸盐反应,
式中
A,E和R具有上述含意;
并且适宜时,在酸受体如碳酸钾存在下,按类似于本发明方法(a)的方式在0~150℃使产物与上述通式(III)的二取代烷反应(参见制备实施例)。
式(XIV)的前体为已知和/或可以由前述已知的方法制备(参见EP-A 386561,EP-A 498188,制备实施例)。
式(VII)提供另外的制备通式(I)化合物的本发明方法(c)中用作原料的化合物的一般性定义。式(VII)中,Q和Z优选或特别是具有与式(I)化合物描述有关的上述业已给出的优选的或特别优选的Q和Z的那些含意。
式(VII)的原料是已知的有机合成化合物。
式(VII)提供在制备通式(I)化合物的本发明方法(d)中用作原料的羟基烷氧基酰胺的一般性定义。式(VII)中,A,Ar,E,G和Z优选,或特别是,具有与式(I)化合物描述有关的上述业已给出的优选或特别优选的A,Ar,E,G和Z含义。
式(XIII)的原料迄今尚未见于文献,作为新物质,它为本申请的一部分。
式(VIII)的新的羟基烷氧基酰胺可以如下获得:使通式(XV)的羧酸衍生物与通式(XVI)的羟胺反应:
其中
Ar,E,G和Z具有上述含意,且
Y代表卤素,羟基或烷氧基,
H2N-O-A-OH(XVI)
式中
A具有上述含意;反应条件为:0℃至150℃温度,适宜时,在酸受体如三乙胺、吡啶或4-二甲基氨基-吡啶存在下,和如果适宜,在稀释剂如二氯甲烷,甲苯或四氢呋喃存在下,(参见制备实施例)。
需作为前体的式(XV)羧酸衍生物是已知的和/或可以由前述已知的方法制备(参见EP-A 178826,EP-A 242081,EP-A382375,EP-A 493711)。
另需作为前体的式(XVI)羟胺也是已知的和/或可以由前述已知的方法制备(参见J.Chem.Soc.Perkin Trans.I 1987,2829-2832)。
本发明的方法(a)、(b)和(c)优选在适合的酸受体存在下进行。适合的酸受体是所有常规无机或有机碱,包括,例如,碱金属或碱土金属的氢化物、氢氧化物、氨化物、醇化物、乙酸盐、碳酸盐或碳酸氢盐,例如,氢化钠,氨基化钠,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,且也包括叔胺,如三甲胺,三乙胺,三丁胺,N,N-二甲基苯胺,N,N-二甲基-苄胺,吡啶,N-甲基哌啶,N,N-二甲基氨基吡啶,二氮杂二环辛烷(DABCO),二氮杂二环壬烯(DBN)或二氮杂二环十一烯(DBU)。
实施本发明方法(a)、(b)和(c)的适合的稀释剂为水和有机溶剂。包括,特别是,脂族、脂环族或芳族的任选卤代的烃类,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,四氯化碳;醚类,如乙醚,二异丙醚,二烷,四氢呋喃或乙二醇二甲醚或乙二醇二乙醚;酮类,如丙酮,丁酮或甲基异丁酮;腈类,如乙腈,丙腈或苯基氰;酰胺类,如N,N-二甲基甲酰胺,N,N-二甲基乙酰胺,N-甲基-N-甲酰苯胺,N-甲基吡咯烷酮或六甲基磷酰三胺;酯类,如乙酸甲酯或乙酸乙酯;亚砜类,如二甲基亚砜;醇类,如甲醇,乙醇,正或异丙醇,乙二醇单甲醚,乙二醇单乙醚,二乙二醇单甲醚,二乙二醇单乙醚;它们与水的混合物,或纯水。
本发明的方法(d)优选在脱水剂存在下进行。适合的脱水剂是常规的脱水化合物,特别是酸酐,如,氧化磷(V)(五氧化二磷)。
实施本发明方法(d)的适合稀释剂是常规的惰性有机溶剂。包括,特别是脂族,脂环族或芳族任选卤代的烃类,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,四氯化碳;醚类,如乙醚,二异丙醚,二烷,四氢呋喃或乙二醇二甲醚或乙二醇二乙醚;酮类,如丙酮,丁酮或甲基异丁基酮;腈类,如乙腈,丙腈或苄腈;酰胺类,如N,N-二甲基甲酰胺,N,N-二甲基乙酰胺,N-甲基-N-甲酰苯胺,N-甲基吡咯烷酮或六甲基磷酰三胺;酯类,如乙酸甲酯或乙酸乙酯;亚砜类,如二甲基亚砜。
实施本发明的方法(a)、(b)、(c)和(d)时,反应温度可以在很宽范围内变化。通常,这些方法可以在-20℃至+200℃间进行,优选在0℃和150℃间的温度。
实施本发明方法(a)时,每摩尔的式(II)羧酸衍生物通常采用1至5摩尔,优选1.0至2.5摩尔的羟胺或羟胺盐酸盐和通常1至10摩尔,优选1.0至5.0ml的式(III)二取代烷。
实施本发明方法(b)时,每摩尔的式(IV)羟基芳基化合物通常采用0.5至2.0摩尔,优选0.9至1.2摩尔的式(V)化合物。
实施本发明方法(c)时,每摩尔的式(VI)卤代化合物通常采用1至5摩尔,优选1.5至3摩尔的式(VII)化合物。
实施本发明方法(d)时,每摩尔的式(VIII)羟基烷氧基酰胺通常采用1至5摩尔,优选1.5至4摩尔的脱水剂。
在所有情况下,由已知的方法进行反应、处理和分离反应产物(参见制备实施例)。
本发明的活性化合物具有强的杀微生物活性且可以实际用来防治有害微生物。活性化合物适合用作植物保护剂,特别是作为杀真菌剂。
植物保护中的杀真菌剂适用于防治根肿菌纲(Plasmodiophoromycetes),卵菌亚纲(Domycetes),壶菌纲(Chytridiomycetes),接合菌亚纲(Zygomycetes),子囊菌纲(Ascomycetes),担子菌纲(Basidiomycetes)和半知菌类(Deuteromycetes)。
上述列出的某些真菌病害的致病生物体可以提到的有例如下列,但决不限于此:
腐霉属,如甘薯白腐病菌;
疫霉属,如马铃薯疫霉菌;
假霜霉属,如Pseudoperonospora humuli或瓜类霜霉病菌;
单轴霉属,如葡萄霜霉病菌;
霜霉属,如Peronospora pisi或油菜霜菌;
白粉菌属,如麦类白粉病菌;
单丝壳属,如黄瓜白粉病球壳菌;
叉丝单囊壳属,如苹果白粉病菌;
黑星菌属,如苹果黑星病菌;
核球壳菌属,如大麦网纹病菌或大麦条纹病(分生孢子形式:
Drechslera,有性繁殖:长蠕孢属);
旋孢腔菌属,如禾旋孢腔菌(分生孢子形式:Drechslera,有性繁殖:长蠕孢属);
单孢锈属,如菜豆单孢锈菌;
柄锈属,如小麦叶锈病菌;
腥黑粉菌属,如小麦网腥黑粉病菌;
黑粉菌属,如裸黄粉菌或燕麦散黑穗病菌;
薄膜革菌属,如稻纹枯病菌;
梨孢菌属,如稻梨孢菌;
镰孢霉属,如黄色镰孢霉菌;
葡萄孢属,如灰绿葡萄孢菌;
壳针孢属,如麦类颖斑枯病壳针孢菌;
小球腔菌属,如Leptosphaeria nodorum;
尾孢菌属,如Cercospora canescens;
交链孢霉属,如甘蓝黑斑病交链孢菌,和假小尾孢菌属,如Pseudocercosporella herpotrichoides。
植物对防治植物病害的所需浓度的该活性化合物的良好耐药性,使其可以处理植物的地上部分、无性繁殖根茎和种子以及土壤。
在本文中,本发明的活性化合物可以特别用来成功地防治果树和作物的病害,例如防治疫霉属病菌,或防治麦类病害,如核球壳菌属病菌。
此外,本发明的活性化合物具有良好的防治下列病害的活性:例如麦类白粉病菌、禾旋孢腔菌、小球腔菌(Leptosphaeria nodorum),假小尾孢菌(Pseudocercosporella herpotrichoides)和禾谷类上的镰孢霉属病菌、防治稻梨孢菌和稻纹枯病菌,且具有广谱的体外活性。
根据其具体的物理和/或化学特性,活性化合物可以转化成常规剂型,如溶液,乳液,悬浮剂,粉剂,泡沫剂,膏剂,颗粒剂,气雾剂,用于种子的聚合物和涂覆组合物细微胶囊,和ULV冷和热雾剂。
这些型剂可以已知的方式生产,例如,将活性化合物与填充剂(即液体溶剂,压力下的液化气体)混合,和/或与固体载体混合,并任选使用表面活性剂(即乳化剂和/或分散剂和/或起泡剂)。用水作填充剂的情况下,有机溶剂也可以用作助溶剂。作为液体溶剂,适合的主要有:芳族化合物,如二甲苯,甲苯或烷基萘,氯代芳族化合物或氯代脂肪烃,如氯代苯类,氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如矿物油馏份,醇类,如丁醇或乙二醇以及其醚和酯,酮类,如丙酮,甲乙酮,甲基异丙基酮或环己酮,强极性溶剂,如二甲基甲酰胺或二甲基亚砜,以及水;液化气填充剂或载体是指环境温度和大气压力下是气体的液体,例如气雾抛射剂,如卤代烃以及丁烷,丙烷,氮气和二氧化碳;固体载体适合的有:粘土,滑石,白垩,石英,硅镁土,蒙脱石或硅藻土,和研碎的合成矿物质,如高分散二氧化硅,矾土和硅酸盐;用于颗粒剂的固体载体适合的有:例如压碎和破碎的天然矿物质如方解石,大理石,浮石,海泡石和白云石,以及有机和无机粉的合成颗粒,和如下有机物的颗粒:锯木屑,椰壳,玉米穗轴和烟茎;乳化剂和/或起泡剂适合的有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯,聚氧乙烯脂肪醇醚,例如,烷芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及白蛋白水解产物;分散剂适合的有:例如,木素亚硫酸废液和甲基纤维素。
制剂中可以使用粘合剂如粉状、颗粒或乳胶形式的羧甲基纤维素和天然和合成聚合物,如阿拉伯胶,聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,如脑磷脂和卵磷脂,和合成磷脂。其它的粘合剂可以是矿物油和植物油。
也可能使用染料,如无机颜料,例如氧化铁,氧化钛和普鲁士蓝,和有机染料,如茜素染料,偶氮染料和金属酞菁染料,和微量营养素如铁、锰、硼、铜、钴、钼和锌盐。
制剂中通常含有重量比0.1至95%的活性化合物,优选0.5至90%。
本发明的活性化合物可以其本身或以其制剂形式,与已知的杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀虫剂的混合物的形式使用,以扩大作用谱,或为防止抗性的逐步建立。在许多情况下,可以获得增效作用,这就是说,混合物的活性超出单个组分的活性。
混合物中特别有利的组分是例如下列化合物:
杀真菌剂:
2-氨基丁烷,2-苯氨基-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-(4-三氟甲基苯甲基)苯甲酰胺;(E)-2-甲氧基亚氨基-N-甲基-2-(2-苯氧苯基)乙酰胺;8-羟基喹啉硫酸盐;(E)-2-{2-[6-(2-氰基-苯氧基)嘧啶-4-氧基]苯基}-3-甲氧基丙烯酸甲酯;(E)-甲氧基亚氨基[α-(邻甲苯氧基)-邻甲苯基]乙酸甲酯;2-苯基苯酚(OPP),Aldimorph,Ampropylfos,敌菌灵,戊环唑,苯霜灵,碘萎灵,苯菌灵,乐杀螨,联苯,双苯三唑醇,灭瘟素,糠菌唑,磺酸丁嘧啶,丁赛特,石硫合剂,敌菌丹,克菌丹,多菌灵,萎锈灵,甲基克杀螨,地茂散,氯化苦,百菌清,乙菌利,硫杂灵,霜脲氰,环唑醇,酯菌胺,防霉酚,苄氯三唑醇,抑菌灵,哒菌清,氯硝胺,乙霉威,恶醚唑,甲嘧醇,烯酰吗啉,烯唑醇,清螨普,二苯胺,dipyrithion,灭菌磷,二噻农,十二烷胍,腙菌酮,克菌散,环氧唑(epoxyconazole),乙嘧啶,氯唑灵,双氯苯嘧啶,苯氰唑,一甲呋萎灵,种衣酯,拌种咯,苯锈啶,丁苯吗啉,乙酸三苯基锡,三苯羟基锡,福美铁,嘧菌腙,氟啶胺,Fludioxonil,氟氯菌核利,fluquinconazole,氟哇唑,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,双胍辛,六氯苯,己唑醇,甲羟异唑,抑霉唑,酰胺唑,双胍辛醋酸盐,异稻瘟净,异菌脲,稻瘟灵,春日霉素,铜制剂如氢氧化铜,环烷酸铜,碱式氯化铜,硫酸铜,氧化铜,喹啉酮和波尔多混合物,双代混剂,代森锰锌,代森锰,嘧菌胺,灭锈胺,甲霜灵,mefconazole,磺菌威,担菌胺,代森联,噻菌胺,腈菌唑,福美镍,nitrothal-isopropyl,氟苯嘧啶醇,甲呋酰胺,恶酰胺,oxamocarb,氧化萎锈灵,perfurazoat,戊菌唑,戊菌隆,匹马菌素,哌啶宁,多氧霉素,烯丙异噻唑,咪鲜安,二甲菌核利,霜霉威,丙环唑,甲基代森锌,定菌磷,啶斑肟,pyrimethanil,咯喹酮,五氯硝基苯,硫磺和硫制剂,戊唑醇,酞枯酸,四氯硝基苯,氟醚唑,噻菌灵,噻菌腈,甲基托布津,福美双,甲基立枯灵,对甲抑菌灵,三唑酮,三唑醇,唑菌嗪,杨菌胺,三环唑,环吗啉,氟菌唑,嗪氨灵,triticonazole,代森锌,福美锌。
杀细菌剂:
拌棉酚,防霉酚,氯定,福美镍,春日霉素,octhilinone,呋喃羧酸,土霉素,烯丙异噻唑,链霉索,酞枯酸,硫酸铜和其它铜制剂。
杀虫剂/杀螨剂/杀线虫剂:
齐墩螨素,乙酰甲胺磷,氟酯菊酯,棉铃威,涕灭威,甲体氯氰菊酯,双甲脒,齐墩螨素(avermectin),AZ60541,azadirachtin,乙基谷硫磷,谷硫磷,三唑锡,苏芸金杆菌,4-溴-2-(4-氯苯基)-1-(乙氧甲基)-5-(三氟甲基)-1H-吡唑-3-甲腈,苯威,丙硫克百威,杀虫螨,乙体氟氯氰菊酯,氟氯菊酯,丁苯威,溴醚菊酯(brofenprox),溴硫磷,混戊威,噻嗪酮,丁酮威,丁基哒螨酮,硫线磷,西维因,克百威,三硫磷,丁硫克百威,巴丹,除线威,chlorethoxyfos,毒虫畏,定虫隆,氯甲硫磷,N-[(6-氯-3-吡啶基)-甲基]-N′-氰基-N-甲基-乙亚氨基酰胺,毒死蜱,甲基毒死蜱,顺式苄呋菊酯,三氟氯氰菊酯,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,异一○五九II,异吸磷II,杀螨隆,地亚农,氯线磷,敌敌畏,dicliphos,百治磷,乙硫磷,伏虫脲,乐果,甲基毒虫畏,二硫磷,乙拌磷,克瘟散,emamectin,高氰戊菊酯,除蚜威,乙硫磷,醚菊酯,丙线磷,醚菊酯,乙嘧硫磷,克线磷,喹螨醚,螨完锡,杀螟硫磷,fenobucarb,苯硫威,双氧威,甲氰菊酯,fenpyrad,唑螨酯,倍硫磷,氰戊菊酯,fipronil,fluazinam,fluazuron,氟螨脲,氟氰戊菊酯,氟虫脲,氟醚菊酯(flufenprox),氟胺氰菊酯,地虫硫磷,安果,噻唑硫磷,fubfenprox,呋线威,六六六,heptenophos,氟铃脲,噻螨酮,咪蚜胺,异稻瘟净,氯唑磷,异丙胺磷,异丙威,唑磷,伊维菌素,入-三氟氯氰菊酯,lufenuron,马拉硫磷,灭蚜硫磷,速灭磷,倍硫磷亚砜,蜗牛敌,虫螨畏,甲胺磷,甲噻硫磷,甲硫威,灭多威,metolcarb,米尔倍菌素,久效磷,moxidectin,二溴磷,NC184,nitenpyram,氧乐果,草肟威,砜吸硫磷,oxydeprofos,马拉硫磷,甲基马拉硫磷,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,甲基嘧啶硫磷,嘧啶硫磷,丙溴磷,发果,pymefrozin,pyrachlophos,吡唑硫磷,苯哒嗪硫磷,pyresmethrin,除虫菊,哒螨酮,pyrimidifen,蚊蝇醚,喹硫磷,水杨硫磷,硫线磷,silafluofen,治螟磷,甲丙硫磷,tebufenozide,tebufenpyrad,特丁嘧啶硫磷,伏虫隆,七氟菊酯,双硫磷,叔丁威,特丁甲拌磷,杀虫畏,thiafenox,硫双灭多威,己酮肟威,甲基乙拌磷,喹线磷,苏芸金菌素,四溴菊酯,triarathen,三唑磷,triazuron,敌百虫,杀虫隆,trimethacarb,完灭硫磷,二甲威,二甲苯威,YI5301/5302,zetamethrin 。
也可与其它已知活性化合物如除草剂、或与化肥和生长调节剂的混合。
活性化合物可以以其制剂或其制备的使用形式使用,所述的制备使用形式如可直接使用溶液,悬浮剂,“Spritz”(可湿性)粉剂,膏剂,可溶性粉剂,粉剂和颗粒剂。它们以常规方法使用,例如浇泼,喷雾,弥雾,撒施,喷粉,起泡,涂刷等等。此外可用超低容量方法使用化合物,或将活性化合物制剂或活性化合物本身注入土壤。也可处理植物的种子。
处理植物部分时,使用形式中的活性化合物浓度可在大范围内变化:
通常,在重量比1和0.0001%之间,优选在重量比0.5和0.001%间使用。
处理种子时,通常每公斤种子需要0.001至50g,优选0.01至10g量的活性化合物。
处理土壤时,在作用点需要活性化合物的浓度为重量比0.00001至0.1%,优选重量比0.0001至0.02%。
制备实施例
实施例1
在20℃下,将1.8g(25mmol)羟胺盐酸化物导入20ml甲醇中,并缓慢加入3.3g氢氧化钾(86%)的20ml甲醇溶液。随后分批加入4.0g(12.8mmol)α-甲氧基亚氨基-α-[2-(2-甲基-苯氧基-甲基)-苯基]-乙酸甲酯,然后将反应混合物在40℃下搅拌,直至反应结束(薄层色谱)。首先将1.7g(12.8mmol)碳酸钾,然后将10.8g(59mmol)1,2-二溴乙烷加入该反应混合物。将该混合物在65℃下搅拌12小时,随后冷却至20℃,并过滤。滤液在水泵真空下浓缩,并将残留物经硅胶柱色谱纯化(甲苯/丙酮,9∶1体积比)。
得到1.4g(理论值的33%)3-{α-甲氧基亚氨基-α-[2-(2-甲基-苯氧基-甲基)-苯基]-甲基}-5,6-二氢-1,4,2-二嗪。
折光指数:nD 20=1.5705。
可以类似实施例1并按照本发明制备方法的一般描述制备的式(I)化合物的其它实例列于下列表1中。
用四甲基硅烷作内标在CDCl3中记录的1H-NMR谱,给出的数据通常是以化学位移作δ值。shifts as δ values
表1:式(I)化合物的实施例
表1中以实施例60给出的化合物,可以例如如下制备:
将0.3g(6mmol)氢化钠的60%浓度的石油白油悬浮液在冰浴下加到1.5g(6mmol)3-[α-甲氧基亚氨基-α-(2-羟基-苯基)甲基]-5,6-二氢-1,4,2-二嗪、0.9g(6mmol)4,6-二氯-嘧啶和30ml N,N-二甲基甲酰胺的混合物中。去除冰浴后,将反应混合物在20℃搅拌15小时。然后在油泵真空下浓缩,残留物用乙酸乙酯处理,用水洗涤,用硫酸钠干燥,并过滤。水泵真空下蒸馏,仔细地将溶剂从滤液中去除。
得到1.9g(理论值的86%)3-{α-甲氧基亚氨基-α-[2-(6-氯-嘧啶-4-氧基)-苯基]-甲基}-5,6-二氢-1,4,2-二嗪,为油状残余物。
表1中以实施例61给出的化合物,可以例如如下制备:
将0.3g(0.9mmol)3-{α-甲氧基亚氨基-α-[2-(6-氯-嘧啶-4-氧基)-苯基]-甲基}-5,6-二氢-1,4,2-二嗪、0.1g(0.9mmol)2-羟基苄腈、0.1g(0.9mmol)碳酸钾、一小勺氯化铜(I)和5ml N,N-二甲基-甲酰胺的混合物在100℃搅拌15小时,然后油泵真空下浓缩,残留物用乙酸乙酯处理,用水洗涤,用硫酸钠干燥,并过滤。将滤液浓缩,残留物用硅胶柱色谱纯化(采用己烷/丙酮,7∶3体积比)。
得到0.3g(理论值的81%)3-{α-甲氧基亚氨基-α-[2-(6-(2-氰基-苯氧基)-嘧啶-4-氧基)-苯基]-甲基}-5,6-二氢-1,4,2-二嗪,熔点82℃。
表1中以实施例58给出的化合物,可以例如如下制备:
将0.5g(2mmol)3-[α-甲氧基亚氨基-α-(2-羟基-苯基)-甲基]-5,6-二氢-1,4,2-二嗪、0.3g(2.2mmol)2-甲基-苄基氯、0.4g(2.5mmol)碳酸钾和10ml乙腈的混合物回流15小时,然后浓缩,残留物用二氯甲烷处理,用水洗涤,用硫酸钠干燥,并过滤。在水泵真空下蒸馏,仔细地将溶剂从滤液中去除。
得到0.4g(理论值的59%)3-{α-甲氧基亚氨基-α-[2-(2-甲基-苄氧基)-苯基]-甲基}-5,6-二氢-1,4,2-二嗪,熔点142℃。
除此之外,依据实施例1可以获得的化合物,可以例如如下制备:
将0.75g(2.4mmol)3-[α-甲氧基亚氨基-α-(2-溴甲基-苯基)-甲基]-5,6-二氢-1,4,2-二嗪和0.70g(6.4mmol)2-甲基-苯酚溶于15ml二甲基甲酰胺,且在将该混合物冷却至-10℃后,缓慢加入0.21g(7.0mmol)氢化钠(80%浓度)。去除冷浴后,将反应混合物在不高于25℃的温度下搅拌14小时,随后倒入大概二倍体积的水中。用乙酸乙酯摇晃后,分离出有机相,用2N氢氧化钠溶液洗涤,用硫酸钠干燥,并过滤。在减压下蒸馏,仔细地将溶液从滤液中去除。
得到0.40g(理论值的49%)3-{α-甲氧基亚氨基-α-[2-(2-甲基-苯氧基-甲基)-苯基]-甲基}-5,6-二氢-1,4,2-二嗪(折光指数:nD 20=1.5705)。
表1中以实施例19给出的化合物,可以例如如下制备:
将0.20g(0.56mmol)N-(2-羟基-乙氧基)-α-甲氧基亚氨基-α-[2-(2,4-二甲基-苯氧基-甲基)-苯基]-乙酰胺溶于3ml氯仿,并在0℃下加入0.25g(1.76mmol)氧化磷(V)。将该反应混合物在20℃搅拌1个时,然后回流下搅拌4小时,随后倒入大概二倍体积的水中,并摇晃。有机相分离出之后,水相用氯仿再萃取三次。合并有机萃取液,用硫酸镁干燥,然后浓缩,并用柱色谱纯化(硅胶;甲苯/丙酮,10∶1)。
得到84mg(理论值的42%)3-{α-甲氧基亚氨基-α-[2-(2,4-二甲基-苯氧基-甲基)-苯基]-甲基}-5,6-二氢-1,4,2-二嗪。
1H NMR(D6-DMSO,δ):4.87,3.84,4.38,4.10ppm。
式(IV)的原料
实施例(IV-1)
将9.0g(28mmol)3-[α-甲氧基亚氨基-α-(2-四氢吡喃-2-氧基)-苄基]-5,6-二氢-1,4,2-二嗪和1.8g离子交换剂“Lewatit SPC108’的90ml甲醇液在20℃下搅拌15小时,然后将该混合物在水泵真空下浓缩,残留物用二氯甲烷处理,并过滤。滤液在水泵真空下浓缩,残留物用硅胶柱色谱纯化(采用己烷/丙酮,7∶3体积比)。
获得的第一级分是0.6g(理论值的9%)Z-{3-[α-甲氧基亚氨基-α-(2-羟基-苯基)-甲基]-5,6-二氢-1,4,2-二嗪},为无定形产物;第二级分是3.3g(理论值的50%)E-{3-[α-甲氧基亚氨基-α-(2-羟基-苯基)-甲基]-5,6-二氢-1,4,2-二嗪},熔点153℃。
式(IX)的原料
实施例(IX-1)
将13.9g(211mmol)85%浓度的氢氧化钾水溶液和17g(58mmol)α-甲氧基亚氨基-α-(2-四氢吡喃-2-氧基-苯基)-乙酸甲酯加入6.8g(98mmol)羟胺盐酸化物的290ml甲醇液中,并将该混合物在40℃下搅拌一小时。加入7.7g(56mmol)碳酸钾,并滴加入42.5g(226mmol)1,2-二溴乙烷。然后将混合物回流15小时,随后在水泵真空下浓缩。残留物用二氯甲烷处理,用水洗涤,用硫酸钠干燥,并过滤。将滤液浓缩,并将残留物经硅胶柱色谱纯化(采用己烷/丙酮,7∶3体积比)。
得到9.0g(理论值的49%)3-[α-甲氧基亚氨基-α-(2-四氢吡喃-2-氧基)-苄基]-5,6-二氢-1,4,2-二嗪,为油状产物。
式(X)的原料
实施例(X-1)
将203g(1.81mol)叔丁醇钾导入2升叔丁醇中,并向其中加入564g(4.93mol)叔丁腈和411g(1.64mol)2-四氢吡喃氧基-苯基乙酸甲酯的500ml叔丁醇溶液。90分钟后,将350g(2.47mol)甲基碘滴加入,并将混合物在20℃搅拌15小时。然后在水泵真空下浓缩,并将残留物用甲基叔丁基醚处理,用硫酸钠干燥,并过滤。残留物用乙醚消化产生结晶,并将该产物经抽吸过滤离析。
得到69.3g(理论值的15%)α-甲氧基亚氨基-α-(2-四氢吡喃)-2-氧基-苯基)-乙酸甲酯,熔点79℃。
式(XI)的原料
实施例(XI-1)
将500g(3.0mol)2-羟基-苯基-乙酸甲酯506g(6.0mol)3,4-二氢吡喃,一小勺对甲苯磺酸和2.5升四氢呋喃在20℃搅拌15小时,然后用冰冷的10%浓度氢氧化钾水溶液搅拌,加入硫酸钠,并将混合物过滤。在水泵真空下蒸馏,仔细地将溶剂从滤液中除去。
得到698g(理论值的99%)2-四氢吡喃氧基-苯基-乙酸甲酯,为油状残留物。
式(VI)的原料
实施例(VI-1)
将0.50g(2.1 3mmol)3-[α-甲氧基亚氨基-α-(2-甲基-苯基)-甲基]-5,6-二氢-1,4,2-二嗪和0.57g(3.2mmol)N-溴-琥珀酰亚胺导入10ml四氯化碳,且加入200mg偶氮异丁腈之后,将混合物回流4小时。再加入0.57g(3.2mmol)N-溴-琥珀酰亚胺后,将混合物再回流一小时。随后冷却并过滤,将滤液浓缩,并将残留物进行色谱(硅胶;甲苯/丙酮,10∶1)处理。
得到20mg(理论值的30%)3-[α-甲氧基亚氨基-α-(2-溴-甲基-苯基)-甲基]-5,6-二氢-1,4,2-二嗪。
1H NMR(CDCl3,δ):4.4ppm。
式(XIII)的原料
实施例(XIII-1)
将19.6g(0.283mol)羟胺盐酸化物导入150ml甲醇,且缓慢加入36.9g(0.565mol)氢氧化钾(86%浓度)的150ml甲醇溶液。然后分批加入30g(0.145mol)α-甲氧基亚氨基-α-(2-甲基-苯基)-乙酸甲酯。在50℃下将混合物搅拌3小时。随后在20℃加入20g(0.145mol)碳酸钾和122g(0.65mol)1,2-二溴乙烷,且将该混合物在65℃下搅拌17小时。将混合物冷却之后,用抽吸进行过滤,将滤液浓缩,并将残留物进行色谱(硅胶;甲苯/丙酮,15∶1)处理。
得到15.2g(理论值的45%)3-[α-甲氧基亚氨基-α-(2-甲基-苯基)-甲基]-5,6-二氢-1,4,2-二嗪。
1H NMR(CDCl3,δ):2.2ppm 。
式(XIV)的原料
实施例(XIV-1)
将187.5g(1.673mol)叔丁醇钾溶于1875ml叔丁醇中。将471.5g(4.57mol)亚硝酸叔丁酯和250g(1.525mol)2-甲基-苯基-乙酸甲酯的500ml叔丁醇溶液计量加入,使中间温度不升至高于50℃。将混合物搅拌90分钟,从20℃升至30℃。然后滴加入326.5g(2.3mol)甲基碘,并将反应混合物在20℃搅拌14小时。随后在水泵真空下蒸馏去除溶液,残留物用2升水处理,并将混合物用乙酸乙酯萃取三次。合并有机相,用硫酸钠干燥,并过滤。将滤液浓缩,残留物用250ml异丙醇处理,并在回流下加入水,直至混合物变浊。
将混合物冷却至0℃并搅拌60分钟之后,将获得的晶体产物在抽吸下过滤离析。
得到84.5g(理论值的27%)α-甲氧基亚氨基-α-(2-甲基-苯基)-乙酸甲酯,熔点53℃。
1H NMR(CDCl3,δ):2.19ppm。
式(VIII)的原料
实施例(VIII-1)
将0.8g(2.36mmol)α-甲氧基亚氨基-α-[2-(2,4-二甲基-苯氧基-甲基)-苯基]-乙酰氯溶于10ml四氢呋喃,并加入0.26g(2.6mmol)三乙胺。然后将溶于10ml四氢呋喃的0.25g(2.6mmol)O-(2-羟乙基)-羟胺在0℃下滴加入。将反应混合物在20℃搅拌2小时,然后倒入水中,并用乙酸乙酯苹取。萃取溶液用硫酸镁干燥,浓缩并进行色谱(硅胶;甲苯/丙酮,10∶1)处理。
得到0.4g(理论值的50%)N-(2-羟基-乙氧基)-α-甲氧基亚氨基-α-[2-(2,4-二甲基-苯氧基-甲基)-苯基]-乙酰胺。
1H NMR(CDCl3,δ):3.65;3.90;9.15ppm。
式(XV)的原料
实施例(XV-1)
将0.93g(2.95mmol)α-甲氧基亚氨基-α-[2-(2,4-二甲基-苯氧基-甲基)-苯基]-乙酸与4.0g(2.9mmol)亚硫酰氯和50mg二甲基甲酰胺混合,并将混合物在回流下搅拌30分钟。在减压下蒸馏,仔细地将更挥发的组份除去。
得到0.95α-甲氧基亚氨基-α-[2-(2,4-二甲基-苯氧基-甲基)-苯基-乙酰氯,为油状残留物。
实施例(XV-2)
将2.0g(6.1mmol)α-甲氧基亚氨基-α-[2-(2,4-二甲基-苯氧基-甲基)-苯基]-乙酸甲酯溶于20ml异丙醇,并加入30ml 1N氢氧化钠溶液。将混合物在40℃搅拌14小时,然后倒入水中。用2N盐酸将其pH调至6,并将获得的晶体产物通过抽吸过滤离析。
得到1.5g(理论值的78%)α-甲氧基亚氨基-α-[2-(2,4-二甲基-苯氧基-甲基)-苯基]-乙酸。
1H NMR(CDCl3,δ):3.9;4.85ppm。
用途实施例
实施例A
大麦网斑病(Pyrenophora teres)保护性防治试验
溶剂:10份重量的N-甲基吡咯烷酮
乳化剂:0.6份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将此乳油用水稀释至所需浓度。
为测试保护性活性,用活性化合物制剂将幼株喷至露水般湿润。喷液层变干后,将植株用大麦网斑病菌分生孢子悬浮液接种。让植株留在20℃和100%相对湿度的培养箱中48小时。
将植株放置在温度大概20℃和相对空气湿度大概80%的温室中。
接种7天后评价该试验。
在此试验中,例如,制备实施例1的化合物在400g/ha.的施用量时显示出100%的防治效果水平。
实施例B
马铃薯晚疫病(Phytophthora)内吸性防治试验
溶剂:4.7份重量的丙酮
乳化剂:0.3份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将此乳油用水稀释至所需浓度。
为测试内吸性能,将活性化合物制剂倒入含有准备用作试验的幼株的标准土中。处理3天后,用马铃薯晚疫病菌的孢子水悬液接种。
将植株留在大概20℃和100%相对空气湿度的培养箱中。
接种3天后,评价该试验。
在此试验中,例如制备实施例1的化合物在活性化合物浓度100ppm时显示出58%的防治效果水平。
实施例C
稻瘟病(Pyricularia)内吸性防治试验
溶剂:12.5份重量的丙酮
乳化剂:0.3份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂混合,并将该浓缩物用水和所述量的乳化剂稀释至所需浓度。
为测试内吸性能,将40ml活性化合物制剂倒入已生长稻秧的标准土中,处理7天后,用稻瘟病菌的孢子水悬液接种稻株,并将其留在25℃和相对空气温度100%的温室中,直至评价之。
接种4天后评价发病率。
在此试验中,例如,制备实施例1的化合物,在100mg/100ml的施用量时显示出80%的防治效果水平。
Claims (1)
1.式(VIII)化合物
其中A、Ar、E具有权利要求1给出的含义,
G代表单键、氧,或代表烷二基、链烯二基、氧杂烯二基、炔二基,它们各自有最多4个碳原子且各自任选由卤素、羟基、C1-C4烷基、C1-C4卤代烷基或C3-C6环烷基取代,或代表下列基团之一:
-Q-CQ-,-CQ-Q-,-CH2-Q-,-Q-CH2-,-CQ-Q-CH2-,
-CH2-Q-CQ-,-Q-CQ-CH2-,-Q-CQ-Q-CH2-,-N=N-,
-S(O)n-,-CH2-S(O)n-,-CQ-,-S(O)n-CH2-,
-C(R4)=N-O-,-C(R4)=N-O-CH2-,-N(R5)-,
-CQ-N(R5)-,-N(R5)-CQ-,-Q-CQ-N(R5)-,
-N=C(R4)-Q-CH2-,-CH2-O-N=C(R4)-,-N(R5)-CQ-Q-,
-CQ-N(R5)-CQ-Q-,-N(R5)-CQ-Q-CH2-,-CQ-CH2-or
-N=N-C(R4)=N-O-,
其中
n代表数字0、1或2,
Q代表氧或硫,
R4代表氢、氰基,或代表烷基、烷氧基、烷硫基、烷氨基或二烷基氨基,它们各在烷基上有1至6个碳原子且各自任选由卤素、氰基或C1-C4烷氧基取代,或代表有3至6个碳原子的环烷基,它们任选由卤素、氰基、羧基、C1-C4烷基或C1-C4烷氧羰基取代,
R5代表氢、羟基、氰基,或代表任选由卤素、氰基或C1-C4烷氧基取代的1至6个碳原子的烷基,或代表任选由卤素、氰基、羧基、C1-C4烷基或C1-C4烷氧羰基取代的3至6个碳原子的环烷基,和
Z代表1至8个碳原子的烷基,它任选由卤素、氰基、羟基、氨基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基或各自可任选由卤素取代的C1-C4烷基磺酰基取代,或代表链烯基或炔基,它们含最多8个碳原子并各自任选由卤素取代,或代表3至6个碳原子的环烷基,它们任选由卤素、氰基、羧基和任选由卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基取代的苯基、C1-C4烷基或C1-C4烷氧羰基取代,或代表各自任选取代的苯基、萘基或任选苯稠合的具5或6个环原子的杂环基,环原子中至少一个代表氧、硫或氮,并且任选另有一或两个环原子代表氮,其中取代基选自:代替两个孪位氢原子的氧、卤素、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、各自为直链或支链的烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,它们各有1至6个碳原子,各自为直链或支键的链烯基或链烯氧基,它们各有2至6个碳原子,各自为直链或支链的卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基,它们各有1至6个碳原子和1至13个相同或不同的卤原子,各自为直链或支链的卤代链烯基、卤代链烯氧基,它们各有2至6个碳原子和1至13个相同或不同的卤原子,各自为直链或支链的烷氨基、二烷基氨基、烷基羰基、烷基羰氧基、烷氧羰基、烷基磺酰氧基、羟亚氨基烷基或烷氧基亚氨基烷基,它们在各自烷基部分有1至6个碳原子,各自为二价的亚烷基或二氧亚烷基,它们各有1至6个碳原子且各自任选由选自卤素和/或1至4个碳原子的直链或支链烷基和/或含1至4个碳原子和1至9个相同或不同的卤原子的直链或支链卤代烷基的相同或不同的取代基单取代或多取代,或3至6个碳的环烷基,杂环基或杂环基甲基,它们各有3至7个环原子,其中各有1至3个环原子是相同或不同的杂原子——氮、氧和/或硫,和苯基、苯氧基、苄基、苄氧基、苯乙基或苯乙氧基,它们在苯基部分任选由选自卤素、氰基、硝基、羧基、氨基甲酰基和/或1至4个碳原子的直链或支链烷基和/或含1至4个碳原子和1至9个相同或不同的卤原子的直键或支链卤代烷基和/或含1至4个碳原子的直链或支链烷氧基和/或含1至4个碳原子和1至9个相同或不同的卤原子的直链或支链卤代烷氧基和/或各自含最多5个碳原子的烷基羰基或烷氧基羰基的相同或不同的取代基单取代或多取代。
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CN2005101250240A Expired - Lifetime CN1803798B (zh) | 1993-08-11 | 1994-07-29 | 制备杀真菌组合物的方法 |
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US6268312B1 (en) | 1994-04-01 | 2001-07-31 | Shionogi & Co., Ltd. | Oxime derivative and bactericide containing the same as active ingredient |
WO1996025406A1 (de) | 1995-02-13 | 1996-08-22 | Bayer Aktiengesellschaft | Fungizide aza-heterocycloalkene |
DE19602095A1 (de) * | 1996-01-22 | 1997-07-24 | Bayer Ag | Halogenpyrimidine |
TW492962B (en) | 1996-05-30 | 2002-07-01 | Bayer Ag | Process for preparing 3-(1-hydroxyphenyl-1-alkoximinomethyl)dioxazines |
DE19706396A1 (de) | 1996-12-09 | 1998-06-10 | Bayer Ag | Verfahren zur Herstellung von 3-(l-Hydroxiphenyl-l-alkoximinomethyl)dioxazinen |
US7521473B2 (en) | 2004-02-25 | 2009-04-21 | Wyeth | Inhibitors of protein tyrosine phosphatase 1B |
US9193698B2 (en) | 2013-07-08 | 2015-11-24 | Advinus Therapeutics, Ltd. | Process for preparing fluoxastrobin |
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- 1994-07-29 DE DE59407240T patent/DE59407240D1/de not_active Expired - Lifetime
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TW297754B (zh) | 1997-02-11 |
RU2258066C2 (ru) | 2005-08-10 |
CN1803798A (zh) | 2006-07-19 |
ZA945991B (en) | 1995-03-13 |
CN1803798B (zh) | 2010-06-16 |
DE59407240D1 (de) | 1998-12-10 |
DE4408005A1 (de) | 1995-02-16 |
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UA48114C2 (uk) | 2002-08-15 |
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