CN1072221C - 3-卤-3-杂芳基羧酸衍生物、制备它们的方法和中间体 - Google Patents
3-卤-3-杂芳基羧酸衍生物、制备它们的方法和中间体 Download PDFInfo
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- CN1072221C CN1072221C CN94191870A CN94191870A CN1072221C CN 1072221 C CN1072221 C CN 1072221C CN 94191870 A CN94191870 A CN 94191870A CN 94191870 A CN94191870 A CN 94191870A CN 1072221 C CN1072221 C CN 1072221C
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- Prior art keywords
- alkyl
- group
- formula
- alkylthio
- phenyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 13
- 239000000543 intermediate Substances 0.000 title description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000001301 oxygen Substances 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- -1 sulfydryl Chemical group 0.000 claims description 146
- 125000005843 halogen group Chemical group 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 41
- 239000002585 base Substances 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000003513 alkali Substances 0.000 claims description 15
- 230000012010 growth Effects 0.000 claims description 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 239000005864 Sulphur Substances 0.000 claims description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- 230000008635 plant growth Effects 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 4
- 238000009333 weeding Methods 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 3
- 230000001276 controlling effect Effects 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 230000002363 herbicidal effect Effects 0.000 claims description 2
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 230000002508 compound effect Effects 0.000 claims 2
- TWAYCBAMBSDJDT-UHFFFAOYSA-N 1-$l^{1}-oxidanylpyrrolidine-2,5-dione Chemical compound [O-][N+]1C(=O)CCC1=O TWAYCBAMBSDJDT-UHFFFAOYSA-N 0.000 claims 1
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 239000011593 sulfur Substances 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 235000013399 edible fruits Nutrition 0.000 description 8
- 239000003630 growth substance Substances 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 7
- 244000299507 Gossypium hirsutum Species 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 5
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 4
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
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- 125000002883 imidazolyl group Chemical group 0.000 description 4
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- 125000003226 pyrazolyl group Chemical group 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- 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 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000002028 Biomass Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
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- 238000003810 ethyl acetate extraction Methods 0.000 description 3
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- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 3
- 238000003306 harvesting Methods 0.000 description 3
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- 125000001425 triazolyl group Chemical group 0.000 description 3
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- 241000335053 Beta vulgaris Species 0.000 description 2
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- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 2
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- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 2
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- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 239000007931 coated granule Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 150000004891 diazines Chemical class 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- QMMLUKRVXWXKSI-UHFFFAOYSA-J dichloromethane;titanium(4+);tetrachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Ti+4].ClCCl QMMLUKRVXWXKSI-UHFFFAOYSA-J 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 125000006202 diisopropylaminoethyl group Chemical group [H]C([H])([H])C([H])(N(C([H])([H])C([H])([H])*)C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000021038 drupes Nutrition 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000010413 gardening Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000007773 growth pattern Effects 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- MELUCTCJOARQQG-UHFFFAOYSA-N hex-2-yne Chemical compound CCCC#CC MELUCTCJOARQQG-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical class CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003924 oil dispersant Substances 0.000 description 1
- 229940113162 oleylamide Drugs 0.000 description 1
- 229950010911 orazamide Drugs 0.000 description 1
- 150000007524 organic acids Chemical group 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- 230000007180 physiological regulation Effects 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 238000013138 pruning Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000013526 red clover Nutrition 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 235000018322 upland cotton Nutrition 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- 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
- C07D413/10—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 aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Abstract
本发明公开了式Ⅰ所示3-卤-3-杂芳基羧酸衍生物,式中,R是甲酰基、CO2H或可水解成COOH的基团,其它取代基的意义如下:
R2和R3是卤原子、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基或C1-C4烷硫基;
X是氮原子或CR13,R13是氢原子,R13或者与R3一起形成其中的1个亚甲基被氧原子代替的亚烷基链或亚烯基链;
R4是未取代或取代的5元或6元杂芳环,它含有1-3个氮原子和/或1个硫或氧原子;
R5是氢原子,取代或未取代的烷基、链烯基、链炔基、环烷基或苯基;
Y是硫原子、氧原子或一单链;以及
Z是卤原子。
Description
式中,R是甲酰基、-CO2H或可水解成COOH的基团,其它取代基的意义如下:
R2是卤原子,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基或C1-C4烷硫基;
X是氮原子或CR13,其中的R13是氢原子,R13或者与R3一起形成其中的一个亚甲基被氧原子代替的3-4元亚烷基或亚烯基;
R3是卤原子,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基,C1-C4烷硫基,或者如上所述R3与R13连接形成5或6元环;
R4是含有1-3个氮原子和/或1个硫或氧原子的5或6元杂芳环,它可带有1个或多个下列基团:卤原子,硝基,氰基,羟基,巯基,氨基,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基,C1-C4烷硫基,C1-C4烷基氨基,二(C1-C4烷基)氨基,C1-C4烷基羰基,C1-C4烷氧基羰基或苯基;
R5是氢原子,C1-C4烷基,C3-C6链烯基,C3-C6链炔基,C3-C8环烷基,C1-C4卤代烷基,C1-C4烷氧基烷基,C1-C4烷硫基烷基或苯基;
Y是硫或氧原子,或是一单键;以及
Z是卤原子。
类似的羧酸衍生物、其中也有3-卤代衍生物已公开于文献中,例如公开于EP-A347811、EP-A400741、EP-A409368、EP-A481512、EP-A517215和早期德国专利申请P4142570(EP-A-548710)中,但它们在3-位上都没有杂芳基。
这些已知化合物的生理活性和选择性并不总是令人满意。
本发明目的是提供改进了对作物的选择性和/或更好除草或生理调节活性的化合物。
我们已知发现,前述的3-卤-3-杂芳基羧酸衍生物可达到上述目的,它们具有突出的除草和植物生长调节活性。
本发明化合物以环氧化物Ⅳ为原料合成,后者用已知方法(例如J.March在Advanced Organic Chemistry,2nd ed.,1983,p.862和p.750中所述的方法),从式Ⅱ所示醛或酮或者烯烃Ⅲ制备:
该反应也可在稀释剂的存在下进行。对反应试剂呈惰性的所有溶剂均可用于此目的。
这些溶剂或稀释剂的示例为:水;脂肪、脂环和芳香烃及其氯化物,如己烷、环己烷、石油醚、石油英、苯、甲苯、二甲苯、二氯甲烷、氯仿、四氯化碳、偏二氯乙烷和三氯乙烷;醚,如二异丙醚、二丁醚、环氧丙烷、二噁烷和四氢呋喃;酮,如丙酮、丁酮、甲基异丙基酮和甲基异丁基酮;腈,如乙腈和丙腈;醇,如甲醇、乙醇、异丙醇、丁醇和乙二醇;酯,如乙酸乙酯和乙酸戊酯;酰胺,如二甲基甲酰胺和二甲基乙酰胺;亚砜和砜,如二甲亚砜和环丁砜;以及碱,如吡啶。
反应优选在0℃至溶剂或溶剂混合物沸点的温度范围内进行。
使用反应催化剂较为有利。适宜催化剂是有机酸和无机酸以及路易斯酸,例如硫酸、盐酸、三氟乙酸、三氟化硼合乙醚和卤化铁(Ⅳ)。
式中,R14是卤原子或R15SO2-,R15为C1-C4烷基、C1-C4卤代烷基或苯基。反应优选在一种上述惰性稀释剂中进行,同时加入适宜碱即可使化合物Ⅵ去质子化的碱,反应温度为室温至溶剂的沸点。
所述碱可以为:碱或碱土金属氢化物,如氢化钠、氢化钾或氢化钙;碳酸盐,即碱金属碳酸盐,如碳酸钠或钾;碱金属氢氧化物,如氢氧化钠或钾;有机金属化合物,如丁基锂;或者碱金属胺化物,如二异丙基胺化锂。
式中,R2、R3和Ⅹ的意义同式Ⅰ中所述。
该反应优选在一种上述惰性稀释剂中进行,同时加入适宜碱、即可将中间体Ⅸ去质子化的碱,反应温度为室温至溶剂的沸点。
除了上述碱以外,也可以使用的三乙胺、吡啶、咪唑或二氮杂双环十一烷的有机碱。
化合物Ⅰ还可以从相应的羧酸、即式中的R为COOH的式Ⅰ化合物制备:首先将它们按常规方式转化成活化形式,如酰氯、酸酐或咪唑酰胺,然后使该活化形成与适宜羟基化合物HOR9反应。该反应可在常规溶剂中进行,并优选在碱的存在下进行,适宜的碱如前所述。也可以将这两步简化,例如使羧酸在脱水剂如碳化二亚胺的存在下作用于羟基化合物。
此外,式Ⅰ化合物也可以从相应的羧酸盐制备,例如从式中的R是COR1的式Ⅰ化合物制备,其中,R1是OM,M例如可以是碱金属阳离子或等价的碱土金属阳离子。这些盐可与许多式R1-A化合物反应,A是常规离核离去基团,例如:卤原子,如氯、溴或碘原子;或者未取代或被卤原子、烷基或卤代烷基取代的芳基或烷基磺酰基,如甲苯磺酰基和甲基磺酰基;或者其它等价离去基团。那些未知的式R1-A化合物(式中的A为活性取代基)可用本领域已知的方法得到。该反应可在碱的存在下、在常规溶剂中进行,适宜的碱如前所述。
a)氢原子;
b)琥珀酰亚氨氧基;
c)5元杂芳环,如吡咯基、吡唑基、咪唑基和三唑基,它们通过氮原子与C=O相连,并且可带有1或2个卤原子、特别是氟和氯原子和/或1或2个下列基团:
C1-C4烷基,如甲基、乙基、1-丙基、2-丙基、2-甲基-2-丙基、2-甲基-1-丙基、1-丁基、2-丁基;
C1-C4卤代烷基、特别是C1-C2卤代烷基,如氟甲基、二氟甲基、三氟甲基、一氯二氟甲基、二氯一氟甲基、三氯甲基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯氟乙基和五氟乙基;
C1-C4卤代烷氧基、特别是C1-C2卤代烷氧基,如二氟甲氧基、三氟甲氧基、一氯二氟甲氧基、1-氟乙氧基、2-氟乙氧基、2,2-二氟乙氧基、1,1,2,2-四氟乙氧基、2,2,2-三氟乙氧基、2-氯-1,1,2-三氟乙氧基和五氟乙氧基,特别是三氟甲氧基;
C1-C4烷氧基,如甲氧基、乙氧基、丙氧基、1-甲基乙氧基、丁氧基、1-甲基丙氧基、2-甲基丙氧基、1,1-二甲基乙氧基、特别是甲氧基、乙氧基、1-甲基乙氧基;
C1-C4烷硫基,如甲硫基、乙硫基、丙硫基、1-甲基乙硫基、丁硫基、1-甲基丙硫基、2-甲基丙硫基、1,1-二甲基乙硫基,特别是甲硫基和乙硫基;
d)R1还可以是基团-(O)m-NR6R7,其中,m为0或1,R6和R7可相同或不同、意义如下
氢原子;
C1-C8烷基,特别是如前所述的C1-C4烷基;
C3-C6链烯基,2-丙烯基、2-丁烯基、3-丁烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1,2-二甲基-2-丙烯基、1-乙基-2-丙烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基和1-乙基-2-甲基-2-丙烯基,特别是2-丙烯基、2-丁烯基、3-甲基-2-丁烯基和3-甲基-2-戊烯基;
C3-C6链炔基,如2-丙炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、1-甲基-2-丁炔基、1,1,-二甲基-2-丙炔基、1-乙基-2-丙炔基、2-己炔基、3-己炔基、4-己炔基、5-己炔基、1-甲基-2-戊炔基、1-甲基-2-戊炔基、1-甲基-3-戊炔基、1-甲基-4-戊炔基、2-甲基-3-戊炔基、2-甲基-4-戊炔基、3-甲基-4-戊炔基、4-甲基-2-戊炔基、1,1-二甲基-2-丁炔基、1,1-二甲基-3-丁炔基、1,2-二甲基-3-丁炔基、2,2-二甲基-3-丁炔基、1-乙基-2-丁炔基、1-乙基-3-丁炔基、2-乙基-3-丁炔基和1-乙基-1-甲基-2-丙炔基,优选2-丙炔基、2-丁炔基、1-甲基-2-丙炔基和1-甲基-2-丁炔基,特别是2-丙炔基;
C3-C8环烷基,如环丙基、环丁基、环戊基、环己基、环庚基和环辛基;
上述烷基、环烷基、链烯基和链炔基还可以带有1-5个、特别是1-3个卤原子(优选氟或氯原子)和/或1或2个下列基团:
*如前所述的C1-C4烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4卤代烷氧基、C3-C6链烯基氧基,C3-C6链烯基硫基,C3-C6链炔基氧基,C3-C6链炔基硫基,这些基团中的链烯基和链炔基部分如前所述;
*C1-C4烷基羰基,例如甲基羰基、乙基羰基、丙基羰基、1-甲基乙基羰基、丁基羰基、1-甲基丙基羰基、2-甲基丙基羰基、1,1-二甲基乙基羰基;
*C1-C4烷氧基羰基,例如甲氧基羰基、乙氧基羰基、丙氧基羰基、1-甲基乙氧基羰基、丁氧基羰基、1-甲基丙氧基羰基、2-甲基丙氧基羰基、1,1-二甲基乙氧基羰基;
*C3-C6链烯基羰基、C3-C6链炔基羰基、C3-C6链烯基氧基羰基和C3-C6链炔基氧基羰基,其中的链烯基和链炔基如前所述;
*未取代的或被卤原子、硝基、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基或C1-C4烷硫基单取代或多取代的苯基,如2-氟苯基、3-氯苯基、4-溴苯基、2-甲基苯基、3-硝基苯基、4-氰基苯基、2-三氟甲基苯基、3-甲氧基苯基、4-三氟乙氧基苯基、2-甲硫基苯基、2,4-二氯苯基、2-甲氧基-3-甲基苯基、2,4-二甲氧基苯基、2-硝基-5-氰基苯基、2,6-二氟苯基;
*二(C1-C4烷基)氨基,如二甲基氨基、二丙基氨基、N-丙基-N-甲基氨基、N-丙基-N-乙基氨基、二异丙基氨基、N-异丙基-N-甲基氨基、N-异丙基-N-乙基氨基、N-异丙基-N-丙基氨基;
R6和R7还可以是苯基,苯基可以被1个或多个如前所述的卤原子、硝基、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基或C1-C4烷硫基取代;或者
R6和R7一起形成环化的取代或未取代C4-C7亚烷基链,该链中可含有选自氧、硫和氮原子的杂原子,如-(CH2)4-、-(CH2)5-、-(CH2)6-、-(CH2)7-、-(CH2)2-O-(CH2)2-、-CH2-S-(CH2)2-、-(CH2)2-O-(CH2)3-、-NH-(CH2)3-、-CH2-NH-(CH2)2-、-CH2-CH=CH-CH2-、-CH=CH-(CH2)3-,适宜的取代基特别是C1-C4烷基;
e)R1还可以是下式所示基团
式中:k为0、1和2;p为1,2,3和4;R8为C1-C4烷基、C1-C4卤代烷基、C3-C6链烯基、C3-C6链炔基或者未取代或取代的苯基,特别是如那些在定义R6和R7时的基团;
f)R1还可以是基团OR9,其中的R9为:
ⅰ)氢原子,碱或碱土金属的阳离子,如锂、钠、钾、钙、镁和钡离子,或者可与周围环境相容的铵离子,如(C1-C4烷基)铵或铵〔NH4 +〕离子;
ⅱ)如前所述的C3-C8环烷基,它可带有1-3个C1-C4烷基;
ⅲ)C1-C8烷基,特别是甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1,2-二甲基丙基、1,1-二甲基丙基、2,2-二甲基丙基、1-乙基丙基、己基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,2-二甲基丁基、1,3-二甲基丁基、2,3-二甲基丁基、1,1-二甲基丁基、2,2-二甲基丁基、3,3-二甲基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基丁基、2-乙基丁基、1-乙基-2-甲基丙基,它们可带有1-5个卤原子、特别是氟和氯原子,和/或1个下列基团:C1-C4烷氧基,C1-C4烷硫基、氰基,C1-C4烷基羰基,C3-C8环烷基,C1-C4烷氧基羰基,苯基,被一个或多个卤原子、硝基、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基和/或C1-C4烷硫基取代的苯基,或苯氧基,特别是那些如前所述的基团;
ⅳ)可带有1-5个、优选1-3个卤原子、特别是氟和/或氯原子,并且带有1个下列基团的如上所述C1-C8烷基:含有1-3个氮原子的5元杂芳环,或者含有1个氮原子和1个氧或硫原子的5元杂芳环,如吡唑基、咪唑基、噁唑基、噻唑基,这些杂芳环通过C原子或-如可能-N原子与烷基相连,并且这些杂芳环可带有1-4个卤原子和/或1或2个下列基团:硝基、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、苯基、C1-C4卤代烷氧基和/或C1-C4烷硫基。特别可提及的是1-吡唑基、3-甲基-1-吡唑基、4-甲基-1-吡唑基、3,5-二甲基-1-吡唑基、3-苯基-1-吡唑基、4-苯基-1-吡唑基、4-氯-1-吡唑基、4-溴-1-吡唑基、1-咪唑基、1-苯并咪唑基、1,2,4-三唑-1-基、3-甲基-1,2,4-三唑-1-基、5-甲基-1,2,4-三唑-1-基、1-苯并三唑基、3-异丙基异噁唑-5-基、3-甲基异噁唑-5-基、噁唑-2-基、噻唑-2-基、咪唑-2-基、3-乙基异噁唑-5-基、3-苯基异噁唑-5-基、3-叔丁基异噁唑-5-基;
ⅴ)在2-位上带有1个下列基团的C2-C6烷基:C1-C4烷氧基亚氨基,C3-C6链炔基氧基亚氨基、C3-C6卤代链烯基氧基亚氨基或苄氧基亚氨基;
ⅵ)C3-C6链烯基或C3-C6链炔基,这些基团又可以带有1-5个卤原子;
ⅶ)R9还可以是带有1-5个卤原子和/或1-3个下列基团的苯基:硝基、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基和/或C1-C4烷硫基,特别是如前所述的那些基团;
ⅶ)通过氮原子相连、并且含有1-3个氮原子的5元杂芳环,如吡唑基、咪唑基、苯并咪唑基、三唑基、苯并三唑基,它们优选通过1-位相连,这些杂芳环还可以带有1或2个卤原子和/或1或2个下列基团:C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基、苯基,C1-C4卤代烷氧基,和/或C1-C4烷硫基。特别是可提及的是1-吡唑基、3-甲基-1-吡唑基、4-甲基-1-吡唑基、3,5-二甲基-1-吡唑基、3-苯基-1-吡唑基、4-苯基-1-吡唑基、4-氯-1-吡唑基、4-溴-1-吡唑基、1-咪唑基、1-苯并咪唑基、1,2,4-三唑-1-基、3-甲基-1,2,4-三唑-1-基、5-甲基-1,2,4-三唑-1-基、1-苯并三唑基、3,4-二氯咪唑-1-基;
ⅸ)R9还可以是下式所示基团
式中,R10和R11可相同或不同,为:
C1-C8烷基、C3-C6链烯基、C3-C6链炔基、C3-C8环烷基,这些基团还可以带有C1-C4烷氧基、C1-C4烷硫基和/或取代或未取代的苯基,特别是如前所述的那些基团;
可被1或多个下列基团取代的苯基:卤原子、硝基、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基或C1-C4烷硫基,这些基团特别是在定义R1时所述的基团;
或者R10和R11一起形成可带有1-3个C1-C4烷基和选自氧、硫和氮的杂原子的C3-C12亚烷基,特别是在定义R6和R7时的基团;
g)R1还可以是基团-NH-SO2-R12,其中的R12是:
C1-C4烷基、C3-C6链烯基、C3-C6链炔基和C3-C8环烷基,特别是那些在定义R1时的基团,这些基团可带有如前所述的C1-C4烷氧基、C1-C4烷硫基和/或苯基;
取代的或未取代的苯基,特别是如前所述的基团。
考虑到它们的生理活性,式Ⅰ所示3-卤-3-杂芳基羧酸衍生物的其它取代基优选具有下列意义:
R2是在定义R1时所述的C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基或C1-C4烷硫基或卤原子,特别是氯原子、甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基,特别优选甲氧基;
X是氮原子或CR13,其中,R13优选为氢原子,或者R13与R3一起形成其中的一个亚甲基被氧原子取代的4元或5元亚烷基或亚烯基,如-CH2-CH2-O-、-CH=CH-O-、-CH2-CH2-CH2-O-、-CH=-CH2O-,特别是氢原子和-CH2-CH2-O-;
R3是定义R1时所述的C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基,C1-C4烷硫基或卤原子,特别是氯原子、甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基,特别是甲氧基,或者如上所述R3与R13一起形成5元或6元环;
R4是5元或6元杂芳基,如呋喃基、噻吩基、吡咯基、吡唑基、咪唑基、三唑基、异噁唑基、噁唑基、异噻唑基、噻唑基、噻二唑基、吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基,例如2-呋喃基、3-呋喃基、2-噻吩基、3-噻吩基、3-异噁唑基、4-异噁唑基、5-异噁唑基、3-异噻唑基、4-异噻唑基、5-异噻唑基、2-噁唑基、4-噁唑基、5-噁唑基、2-噻唑基、4-噻唑基、5-噻唑基、2-咪唑基、4-咪唑基、5-咪唑基、2-吡咯基、3-吡咯基、4-吡咯基、3-吡唑基、4-吡唑基、5-吡唑基、2-吡啶基、3-吡啶基、4-吡啶基、噁-2,4-二唑基、噁-3,4二唑基、噻-2,4-二唑基、噻-3,4-二唑基和三唑基,这些杂芳环可带有1个或多个下列基团:卤原子,硝基,氰基,羟基,巯基,氨基,C1-C4烷基,C1-C4烷氧基,C1-C4烷硫基,C1-C4卤代烷基,C1-C4卤代烷氧基,C1-C4烷基氨基,二(C1-C4烷基)氨基,C1-C4烷基羰基,C1-C4烷氧基羰基和苯基,它们的一般意义和优选情况如前所述;
R5是氢原子,如前所述的C1-C4烷基、C3-C6链烯基、C3-C6链炔基、C3-C8环烷基、C1-C4卤代烷基、C1-C4烷氧基烷基、C1-C4烷硫基烷基或苯基;
Y是硫原子、氧原子或一单键;以及
Z是卤原子。
优选的化合物Ⅰ中,R5是甲基,X是CH,并且R2和R3是甲氧基。更优选的化合物Ⅰ中,R5是甲基,X是CH,Z是氟原子,并且R2和R3是甲氧基。此外,R1优选为基团OR9,特别是OH和O-(C1-C4烷基)。
Y优选为硫原子,并更优选为氧原子。
特别优选的式Ⅰ化合物列于下列Ⅰ中。在该表中和表1和2中给出的R4的定义是优选的,与其它基团定义无关。
表ⅠR1 R4 R5 R2 R3 X Y ZOH 2-噻吩基 CH3 OCH3 OCH3 CH S FOH 2-噻吩基 H OCH3 OCH3 CH S FOH 2-噻吩基 CH3 OCH3 OCH3 CH O FOH 2-噻吩基 H OCH3 OCH3 CH O FOH 3-噻吩基 CH3 OCH3 OCH3 CH O FOCH3 3-氯-2-噻吩基 CH3 OCH3 OCH3 CH O FOC2H5 2-氯-3-噻吩基 CH3 OCH3 OCH3 N O ClON(CH3)2 2-呋喃基 CH3 CF3 CF3 CH S BrON-C(CH3)2 4-溴-2-呋喃基 CH3 OCF3 OCF3 CH O FNHSO2C6H5 3-呋喃基 CH3 CH3 CH3 CH O FNHC6H5 4-硝基-3-呋喃基 CH3 Cl Cl CH O ClONa 2-吡咯基 CH3 OCH3 -OCH2-CH2- S BrOCH2-C≡CH 5-氰基-2-吡咯基 CH3 OCH3 CF3 CH O FOH 3-吡咯基 CH3 OCH3 OCF3 CH O FOCH3 5-甲基-3-吡咯基 CH3 OCH3 CH3 CH O FOC2H5 3-吡唑基 CH3 OCH3 Cl CH S ClON(CH3)2 4-吡唑基 CH3 OCH3 OCH3 CH O ClON-C(CH3)2 5-吡唑基 CH3 OCH3 OCH3 CH O BrNHSO2C6H5 2-咪唑基 CH3 OCH3 OCH3 CH O BrNHC6H5 4-咪唑基 CH3 CF3 CF3 N S FR1 R4 R5 R2 R3 X Y ZONa 1-乙基-5-咪唑基 CH3 OCF3 OCF3 N O FO-CH2-C≡CH 3-异噁唑基 CH3 CH3 CH3 N O FOH 4-异噁唑基 CH3 Cl Cl N O FOCH3 5-异噁唑基 CH3 OCH3 -O-CH2-CH2- O ClOC2H5 2-噁唑基 CH3 OCH3 CF3 N S BrON(CH3)2 4-噁唑基 CH3 OCH3 OCF3 N O ClON(CH3)2 5-噁唑基 CH3 OCH3 CH3 N O BrNHSO2C6H5 3-异噻唑基 CH3 OCH3 Cl N O FNHC6H5 4-异噻唑基 CH3 OCH3 OCH3 CH S FONa 5-异噻唑基 CH3 OCH3 OCH3 CH S FO-CH2-C≡CH 2-噻唑基 CH3 OCH3 OCH3 N S FOH 4-噻唑基 CH3 CF3 CF3 CH O FOCH3 5-噻唑基 CH3 OCF3 OCF3 CH O BrOC2H5 1,2,3-三唑-4-基 CH3 CH3 CH3 CH O BrON(CH3)2 2-嘧啶基 CH3 Cl Cl CH O ClON(CH3)2 4-嘧啶基 CH3 OCH3 -O-CH2-CH2- S FNHSO2C6H5 5-嘧啶基 CH3 OCH3 CF3 N S FNHC6H5 2-吡啶基 CH3 OCH3 OCF3 N S FONa 3-甲氧基-2-吡啶基 CH3 OCH3 CH3 N O FO-CH2-C≡CH 4-甲硫基-2-吡啶基 CH3 OCH3 Cl N O FOCH3 5-三氟甲基-2-吡啶基 CH3 OCH3 -O-CH2-CH2- O ClOC2H5 3-吡啶基 CH3 OCH3 CF3 N S BrON(CH3)2 2-羟基-3-吡啶基 CH3 OCR3 OCF3 N O FR1 R4 R5 R2 R3 X Y ZON(CH3)2 4-二甲氨基-3-吡啶基 CH3 OCH3 CH3 N O FNHSO2C6H5 5-巯基-3-吡啶基 CH3 OCH3 Cl N O FNHC6H5 4-吡啶基 CH3 OCH3 OCH3 CH S FONa 2-苯基-4-吡啶基 CH3 OCH3 OCR3 CH S ClO-CH2-C≡CH 3-甲氧羰基-4-吡啶基 CH3 OCH3 OCH3 N S ClOH 2,6-二甲基-3-吡啶基 CH3 CF3 CF3 CH O FOCH3 2,4-二羟基-3-吡啶基 CH3 OCF3 OCF3 CH O BrOC2H5 2,6-二异丙基-4-吡啶基CH3 CH3 CH3 CH O FON(CH3)2 噁-2,4-二唑基 CH3 Cl Cl CH O FON-C(CH3)2 噻-3,4-二唑基 CH3 OCH3 -O-CH2-CH2- S ClNHSO2C6H5 1,2,4-三唑-2-基 CH3 OCH3 CF3 N S FNHC6H5 四唑基 CH3 OCH3 OCF3 N S FONa 噁-3,4-二唑基 CH3 OCH3 CH3 N O FO-CH2-C≡CH 噻-2,4-二唑基 CH3 OCH3 Cl N O F
化合物Ⅰ或含有它们的除草剂组合物以及它们的与环境可相容盐(如碱和碱土金属盐)可以很好地控制作物如小麦、水稻、玉米、大豆和棉花中的阔叶杂草和禾木科杂草,而不损害作物,特别是它们可在低用量下达到良好的效果。它们例如可以直接喷雾的溶液、粉状物、悬浮液(高浓度水、油或其它悬浮液)或分散剂、乳液、油分散剂、膏剂、粉剂、撒播剂或颗粒剂的形式,通过喷洒、雾化、撒粉、撒播或浇灌而使用。应用的方法根据意欲的目的而定,但无论如何,都应保证本发明活性成分尽可能分散均匀。
化合物Ⅰ一般适于制成待喷洒溶液、乳液、膏剂或油分散制剂。适宜的惰性添加剂为:中至高沸点矿物油,如煤油或柴油以及煤焦油;植物和动物油;脂肪、环状和芳香烃,如甲苯、二甲苯、石蜡烃、四氢化萘、烷基化萘或其衍生物;甲醇,乙醇,丙醇,丁醇,环己醇,环己酮,氯苯,异佛尔酮;或者强极性溶剂,如N,N-二甲基甲酰胺、二甲基亚砜、N-甲基吡咯烷酮或水。
含水应用形式可通过加入水用浓缩乳液、分散液、膏剂、可湿性粉剂或可水分散的颗粒制备。为制备乳液,可将膏剂或油分散体本身或溶于油或溶剂中后,借助于湿润剂、增粘剂、分散剂或乳化剂在水中均化、此外,还可以制备适于用水稀释的由活性成分、湿润剂、增粘剂、分散剂或乳化剂和(如需要)溶剂或油组成的浓缩物。
适宜表面活性剂是芳香磺酸如木素磺酸、酚磺酸、萘磺酸和二丁基萘磺酸的碱金属盐、碱土金属盐或铵盐,以及脂肪酸、烷基和烷芳基磺酸盐,烷基硫酸盐,月桂基醚硫酸盐和脂肪醇硫酸单酯盐,以及硫酸化十六、十七和十八烷醇的盐,和脂肪醇乙二醇醚盐,磺化萘及其衍生物与甲醛的缩合物,萘或萘磺酸与酚和甲醛的缩合产物,聚氧乙烯辛酚醚,乙氧基化的异辛基苯酚、辛基苯酚或壬基苯酚,烷基苯酚基或三丁基苯基聚二醇醚,烷芳基聚醚醇,异十三烷醇,脂肪醇/环氧乙烷缩合物,乙氧基化的蓖麻油,聚氧乙烯或聚氧丙烯烷基醚,十二烷醇聚二醇醚乙酸酯,山梨醇酯,木素-亚硫酸废液或甲基纤维素。
颗粒、撒插物和粉剂可通过将活性成分与固体载体混合或共同研磨来制备。
将活性成分结合于固体载体上,可以制得颗粒制剂,例如包衣颗粒、浸渍颗粒和均相颗粒。固体载体为:矿物土,如硅酸、硅胶、硅酸盐、滑石、高岭土、石灰石、石灰、白垩、陶土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁;粉碎的合成物、化肥,如硫酸铵,磷酸铵、硝酸铵、脲;以及植物产品,如面粉、磨碎的树皮、木材或坚果壳,纤维素粉;或者其它固体载体。
制剂通常含有0.01%-95%wt、优选0.5%-90%wt的活性成分。活性成分的纯度为90%-100%、优选95%-100%(根据NMR谱)。
本发明化合物Ⅰ例如可按下述方法制成制剂:
Ⅰ.将20重量份化合物NO.2.17溶于一混合物中,该混合物由80重量份烷基化苯、10重量份8-10mol(摩尔)环氧乙烷加合到1molN-羟乙基油酰胺上的加合物、5重量份十二烷基苯磺酸钙和5重量份40mol环氧乙烷加合到1mol蓖麻油上的加合物组成。将该溶液倒入100,000重量份水中,并精细分散,得到含0.02%wt活性成分的水分散液。
Ⅱ.将20重量份化合物No.2.1溶于一混合物中,该混合物由40重量份环己酮、30重量份异丁醇、20重量份7mol环氧乙烷加合到1mol异辛基苯酚上的加合物和10重量份40mol环氧乙烷加合到1mol蓖麻油上的加合物组成。将该溶液倒入100,000重量份水中,并精细分散,得到含有0.02%wt活性成分的水分散液。
Ⅲ.将20重量份活性成分No.2.17溶于-混合物中,该混合物由20重量份环己酮、65重量份沸程210°-280℃的矿物油级分和10重量份40mol环氧乙烷加合到1mol蓖麻油上的加合物组成。将该溶液倒入100,000重量份水中,并精细分散,得到含有0.02%wt活性成分的水分散液。
Ⅳ .将20重量份活性成分No.2.2与3重量份二异丁基萘-α-磺酸钠、17重量份得自亚硫酸废液的木素磺酸钠和60重量份硅胶粉彻底混合,并将该混合物在锤磨机中研磨。将该混合物精细分散于20,000重量份水中,得到含有0.1%wt活性成分的喷洒混合物。
Ⅴ.将3重量份活性成分No.2.17与97重量份细粉高岭土混合。得到含有3%wt活性成分的粉剂。
Ⅵ.将20重量份活性成分No.2.17与2重量份十二烷基苯磺酸钙、8重量份脂肪醇聚二醇醚、2重量份苯酚/脲/甲醛缩合物的钠盐和68重量份石蜡烃油紧密掺合。得到稳定的油分散体。
可在芽前或芽后施用。如果某些作物不耐本发明的活性成分,可采用一定的施用技术,借助于喷洒设备,使活性成分尽量少地与这些敏感作物的叶片接触,而使活性成分到达位于下方的不希望植物的叶片上,或者到达裸露土壤表面上(post-directed,lay-by)。
根据欲达到目的、季节、目标植物和生长期,活性成分的施用率为0.001-5kg/ha,优选为0.01-2kg/ha。
考虑到施用方法的多样性,本发明化合物或含有它们的组合物可用于许多其它作物上,以抑制不希望的植物生长。适宜的作物例如为:
洋葱,凤梨,花生,石刁柏,甜菜,欧洲油菜,芜菁甘蓝,芜菁,茶,红花,美洲山核桃,柠檬,甜橙,阿拉伯咖啡(Coffea canephora,大咖啡),黄瓜,狗牙根,胡萝卜,油棕,草莓,大豆,陆地棉(树棉、草棉、Vitifolium棉),向日葵,巴西橡胶,裸大麦,啤酒花,甘薯,核桃,兵豆,亚麻,Lycopersion lycopersicum,苹果,木薯,紫花苜蓿,香蕉,烟草(黄花烟草),欧橄榄,陆稻,棉豆,菜豆,云杉,松,豌豆,甜樱桃,桃,洋梨,红醋栗,蓖麻,甘蔗,黑麦,马铃薯,芦栗(高梁),可可,红车轴草,小麦,硬粒小麦,蚕豆,葡萄,玉米。
式Ⅰ化合物可以不同方式影响植物的整个生长阶段,因此可用作生长调节剂,对植物生长调节的不同活性主要决定于:
a)植物种类,
b)相对于植物的生长阶段和季节的施用时机,
c)施用的位置和方法(例如种子处理、土壤处理、叶片施用或树茎干注射),
d)气候因素,例如温度、降雨量以及日长和光强度,
e)土壤情况(包括施肥情况),
f)活性成分的配方和应用方式,以及
g)施用的活性成分的浓度。
在各种可能的用途中,式Ⅰ化合物在植物种植、农业和园艺中作为植物生长调节剂的一些应用如下所述。
A.根据本发明使用的化合物可用于强烈抑制植物的营养生长,因而可抑制纵生长。
因此,处理过的植物变矮,此外,叶片的颜色变深。
这种应用在实践上的意义是降低杂草生长强度和用于易倒伏的作物,如谷物、玉米、向日癸和大豆。由于具有较矮和强壮的茎干,降低或避免了这些植物在收获前由于恶劣天气条件而倒伏的危险。
另一重量方面是使用生长调节剂抑制棉花的纵生长和改变棉花的成熟期。这使得这种重要作物能够完全机械化收获。
对于果树和其它树,使用生长调节剂可以降低剪枝的花费。此外,借助于生长调节剂可打破果树的大小年结果现象。
通过使用生长调节剂,还可以促进或抑制植物的侧枝。如果为利于叶片生长而需要抑制侧条(根出条)的形成时,例如对于烟草植物,这是很有意义的。
对于冬天的油菜,使用生长调节剂例如还可以显著提高它的耐霜冻能力。一方面,抑制了植物的纵生长和枝叶生长过于繁茂或植物的生物量(它们因此对霜特别敏感),另一方面,延迟了油菜幼苗在播种后和冬天霜降前这一段时间之间的生长。这也消除了在过早落花、进入生殖期的植物上发生霜降的危险。对于其它农作物、如冬天里的谷物也是这样,借助于本发明化合物的处理,使它们在秋天良好地进入分蘖期、但又不会在入冬时生长过旺也是有益的。所有这些都可降低植物对霜的敏感性和降低感染各种病害(例如真菌病害)的危险,这是由于植物具有较少量的叶片或植物生物量。
B.生长调节剂可以提高植物产量,植物的各部位和植物的组分含量都可以被提高。例如,可以诱使生长较大量的芽、花、叶、果实、种子核、根和块茎,提高甜菜、甘蔗和柑桔中的糖分含量,提高谷物或大豆中的蛋白质含量,或者刺激橡胶树流出更多的胶乳。
式Ⅰ化合物通过影响植物的代谢、或者促进或抑制其营养和/或生殖生长,可以提高植物产量。
C.最后,植物生长调节剂可以缩短或延长生育期,并且可以在收割前或收割后促进或延缓植物收获部位的成熟。
在经济上很有意义的一个方面例如是便于收获,它可以使果实脱离果树的时间比较集中,并且可降低果子在树上的附着强度,例如柑桔、橄榄或者各种梨果、核果或坚壳果。同样的机制,它可以促进植物的果实或叶与枝条之间分离组织的形成,这对于很好地控制有用作物如棉花的脱叶也是很重要的。
D.此外,使用生长调节剂可降低耗水量。使用本发明的物质,可以降低灌溉强度,这在经济上更为有利,因为
-降低气孔张开度,
-形成较厚的表皮的角质层,
-改进了根深入土壤中的状况,以及
-更结实的生长改善了植物生长的微环境。
化合物Ⅰ特别适用于降低作物如大麦、油菜和小麦的茎干高度。
根据本发明使用的式Ⅰ所示活性成分可借助于喷洒,通过种子(以种子处理产品的形式)、或通过土壤即通过根、以及(优选)通过叶片施用到作物上。
由于植物对于本发明化合物具有很好的耐受性,所以活性成分的施用率不很严格。最佳施用率根据意欲的的、季节、目标植物和生长阶段而变化。
处理种子时,活性成分的需要量一般为0.001-50g/kg种子、优选0.01-10g/kg种子。
处理叶片和土壤时,施用率为0.001-10kg/ha、优选0.01-3kg/ha、特别是0.01-0.5kg/ha就足够了。
为拓宽活性谱和达到协同效应,式Ⅰ化合物可以与许多其它类除草剂或生长调节活性成分一起混合使用。形成混合物的适宜组分例如是二嗪类、4H-3,1-苯并噁嗪衍生物、苯并噻二嗪酮类、2,6-二硝基苯胺类、N-苯基氨基甲酸酯类、硫代氨基甲酰酯类、卤代羧酸类、三嗪类、酰胺类、脲类、二苯醚类、三嗪酮类、尿嘧啶类、苯并呋喃衍生物、在2-位例如带有羧基或酰亚氨基的环己烷-1,3-二酮衍生物、喹啉羧酸衍生物、咪唑啉酮类、磺酰胺类、磺酰基脲类、芳氧基或杂芳氧基苯氧基丙酸及其盐、酯和酰胺,等。
此外,可以单独施用式Ⅰ化合物,或与其它除草剂组合使用,也可以与其它植物保护剂、如农药或防治植物病理性真菌或细菌的药剂混合使用。与用以补充养份和痕量元素的矿物盐溶液混合使用也是有益的。另外还可加入非植物毒性油和油浓缩物。
合成实施例
式Ⅵ化合物的合成
实施例1
3-氟-3-(2-噻吩基)-2-羟基丁酸甲酯
将19.5g(100mmol)3-(2-噻吩基)-2,3-环氧丁酸甲酯溶于50ml无水二氯甲烷中,并将其滴加到100ml氟化氢/吡啶复合物(70%HF)在100ml无水二氯甲烷中的溶液中。在室温下经过1小时后,将该反应溶液搅拌下倒入150ml冰水中。有机相用碳酸氢盐溶液和水洗涤,用硫酸镁干燥,并浓缩。残余物在加入少量乙酸乙酯的石油醚中重结晶。
产量:17.2g(79%)。
实施例2
3-氯-3-(3-吡啶基)-2-羟基丁酸甲酯
将0.8g(20mmol)LiCl溶于100ml绝对四氢呋喃(THF)中,将该溶液冷却至-20℃,并滴加入20ml四氯化铁二氯甲烷中的1M溶液。将该混合物在-20℃搅拌30分钟后,将其冷却至-78℃,并滴加入在50ml THF中的3.8g(20mmol)3-(3-吡啶基)-2,3-环氧丁酸甲酯。该混合物加热至室温后,继续搅拌6小时,蒸去溶剂,并将残余物在乙酸乙酯和水之间分配。水相用乙酸乙酯萃取,并将合并的有机相用硫酸钠干燥,并浓缩。残余物用正己烷/乙酸乙酯混合物在硅胶上色析提纯。蒸去溶剂后,得到2.9g浅黄色油状物。
产率:63%
以相似方法制备表1所列化合物。
表Ⅰ其中的R1=OCH3的式Ⅵ所示中间体No. R4 R5 Z 非对映体M.p.[℃]1.1 2-噻吩基 CH3 F 1∶11.2 3-吡啶基 CH3 Cl 2∶11.3 2-噻吩基 H F1.4 3-噻吩基 CH3 F1.5 3-噻吩基 H F1.6 2-呋喃基 CH3 F1.7 2-呋喃基 H F1.8 3-呋喃基 CH3 F1.9 3-呋喃基 H F1.10 2-吡啶基 CH3 F1.11 3-吡啶基 CH3 F1.12 4-吡啶基 CH3 F1.13 2-噻唑基 CH3 F1.14 2-吡咯基 CH3 F1.15 3-异噁唑基 CH3 F1.16 1-甲基-2-吡咯基 CH3 F1.17 3-甲基-2-噻吩基 CH3 F1.18 1-甲基-3-吡咯基 CH3 F1.19 5-甲基-2-呋喃基 CH3 F1.20 2,5-二甲基-2-噻吩基 CH3 F
式Ⅰ化合物的合成
实施例3
3-(2-噻吩基)-3-氟-2-〔(4,6-二甲氧基嘧啶-2-基)氧基〕丁酸甲酯
将2.2g(10mmol)3-(2-噻吩基-3-氟-2-羟基丁酸甲酯(化合物1.1)溶于40ml二甲基甲酰胺中,并加入0.3g(12mmol)氢化钠。将该混合物搅拌1小时,然后加入2.2g(10mmol)4,6-二甲氧基-2-甲基磺酰基嘧啶。将该混合物在室温下搅拌24小时后,用10ml水将其水解,用乙酸将pH值调为5,并在高真空下蒸去溶剂。残余物用乙酸乙酯收集,用水洗涤,用硫酸钠干燥,并蒸去溶剂。残余物用10ml甲基叔丁基醚处理,并抽滤出形成的沉淀物。干燥后,得到1.8g白色粉末。
产率:61%(非对映体混合物1∶1)。
实施例4
3-(2-噻吩基-3-氟-2-〔(4,6-二甲氧基嘧啶-2-基)氧基〕-丁酸
将0.9g(3mmol)3-(2-噻吩基)-3-氟-2-(4,6-二甲氧基嘧啶-2-基)氧基丁酸甲酯(得自实施例3)溶于20ml甲醇和20ml四氢呋喃中,并加入3.7g浓度为10%的NaOH溶液。将该混合物在60℃搅拌6小时,在室温搅拌12小时,减压蒸去溶剂,残余物用100ml水收集。水相用乙酸乙酯萃取,随后用稀盐酸将pH值调至1-2,并用乙酸乙酯萃取。将混合物用硫酸镁干燥、并蒸去溶剂后,向残余物中加入少量丙酮,抽滤出形成的沉淀物。干燥后得到0.8g白色粉末。
产率:89%(非对映体混合物3∶2)
实施例5
3-(2-噻吩基)-3-氟-2-〔(4,6-二甲氧基嘧啶-2-基)硫基〕丁酸甲酯
将5.5g(25mmol)3-(2-噻吩基)-3-氟-2-羟基丁酸甲酯(化合物1.1)溶于50ml二氟甲烷中,加入3g(30mmol)三乙胺,并在搅拌下加入3.2g(28mmol)甲磺酰氯。将该混合物在室温搅拌2小时,用水洗涤,用硫酸镁干燥,并减压浓缩。残余物用二甲基甲酰胺(DMF)收集,并将其在0℃加到12.9g(75mol)4,6-二甲氧基嘧啶-2-硫醇和8.4g(100mmol)碳酸氢钠在100md DMF中的悬浮液中。将该混合物在室温搅拌2小时,并在60℃搅拌2小时后,将该混合物倒入1升冰水中,并抽滤出形成的沉淀物。干燥后,得到2.5g白色粉末。
产率:31%(非对映体混合物1∶1)。
类似于上述实施例,制备表2中所示的化合物
[℃]2.1 2-噻吩基 F CH3 O OCH3 1∶12.2 2-噻吩基 F CH3 O OH 3∶22.3 2-噻吩基 F CH3 S OCH3 1∶12.4 2-噻吩基 F CH3 S OH2.5 2-噻吩基 F H O OCH32.6 2-噻吩基 F H O OH2.7 3-噻吩基 F CH3 O OCH32.8 3-噻吩基 F CH3 O OH2.9 3-噻吩基 F H O OCH32.10 3-噻吩基 F H O OH2.11 2-呋喃基 F CH3 O OCH32.12 2-呋喃基 F CH3 O OH2.13 3-呋喃基 F CH3 O OCH32.14 3-呋喃基 F CH3 O OH2.15 2-吡啶基 F CH3 O OCH32.16 2-吡啶基 F CH3 O OH2.17 3-吡啶基 F CH3 O OCH3 3∶1 154-1562.18 3-吡啶基 F CH3 O OH2.19 4-吡啶基 F CH3 O OCH32.20 4-吡啶基 F CH3 O OH*非对映体之比
应用实施例
用温室试验证明了式Ⅰ所示3-(杂)芳基羧酸衍生物的除草活性
所用培养容器是盛有含有3.0%腐殖土的壤质土的塑料花盆。不同试验植物的种子分别栽培。
用于芽前处理时,将活性成分悬浮或乳化于水中,并在插种后用能均匀喷洒的喷雾喷头直接施用。为促进发芽和生长,将这些容器轻微浇水,随后罩以透明塑料薄膜,直至这些植物已生根发芽。除非由于活性成分的抑制,这些覆盖能使试验植物均匀发芽。
在芽后处理时,根据生长方式,首先使试验植物生长至3-15cm的高度,然后用悬浮或乳化于水中的活性成分处理。为此,或者将试验植物直接播种并在同一环境中生长,或者首先在幼苗时分别培育、然后在处理前几天转移至试验容器中。
根据植物的种属,将植物保持在10-25℃或20-35℃。试验时间为2-4星期。此间观察植物生长情况,并评价它们对各种处理的反应。
评价结果分0-100个等级。100表示植物没有发芽或至少地上部分完全死亡,0表示没有影响或生长正常。
Claims (10)
式中,R是甲酰基、-CO2H或可水解成COOH的基团,其它取代基的意义如下:
R2是卤原子,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基或C1-C4烷硫基;
X是氮原子或CR13,其中的R13是氢原子,R13或者与R3一起形成其中的一个亚甲基被氧原子代替的3-4元亚烷基或亚烯基;
R3是卤原子,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基,C1-C4烷硫基,或者如上所述R3与R13连接形成5或6元环;
R4是含有1-3个氮原子和/或1个硫或氧原子的5或6元杂芳环,它可带有1个或多个下列基团:卤原子,硝基,氰基,羟基,巯基,氨基,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基,C1-C4烷硫基,C1-C4烷基氨基,二(C1-C4烷基)氨基,C1-C4烷基羰基,C1-C4烷氧基羰基或苯基;
R5是氢原子,C1-C4烷基,C3-C6链烯基,C3-C6链炔基,C3-C8环烷基,C1-C4卤代烷基,C1-C4烷氧基烷基,C1-C4烷硫基烷基或苯基;
Y是硫或氧原子,或是一单键;以及
Z是卤原子。
2.根据权利要求1的式Ⅰ所示3-卤-3-杂芳基羧酸衍生物,式中R是下式所示基团
式中R1的意义如下:
a)氢原子;
b)琥珀酰亚氨基氧基;
c)通过氮原子相连的5元杂芳环,它含有2个或3个氮原子,并且还可带有1个或2个卤原子和/或1个或2个下列基团:C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基和/或C1-C4烷硫基;
d)基团-(O)m-NR6R7,
式中,m是0或1,并且R6和R7可相同或不同,意义如下:
氢原子;
C1-C8烷基、C3-C6链烯基、C3-C6链炔基、C3-C8环烷基,这些基团上可带有1-5个卤原子和/或1或2个下列基团:C1-C4烷氧基,C3-C6链烯基氧基,C3-C6链炔基氧基,C1-C4烷硫基,C3-C6链烯基硫基,C3-C6链炔基硫基,C1-C4卤代烷氧基,C1-C4烷基羰基,C3-C6链烯基羰基,C3-C6链炔基羰基,C1-C4烷氧基羰基,C3-C6链烯基氧基羰基,C3-C6链炔基氧基羰基,二(C1-C4烷基)氨基,C3-C8环烷基,苯基,被卤原子、硝基、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基或C1-C4烷硫基单取代或多取代的苯基;
可被1个或多个下列基团取代的苯基:卤原子,硝基,氰基,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基,或C1-C4烷硫基;
R6和R7一起形成环化的取代或未取代C4-C7亚烷基链,或者一起形成具有1个选自氧、硫或氮的杂原子的环化的取代或未取代C3-C6亚烷基;
式中:R8是C1-C4烷基,苯基,被卤原子、硝基、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基或C1-C4烷硫基取代的苯基,C1-C4卤代烷基,C3-C6链烯基或C3-C6链炔基;P为1,2,3或4;以及k为0,1或2;
f)基团OR9,式中,R9为:
ⅰ)氢原子,碱金属阳离子,等价的碱土金属阳离子,铵阳离子,或有机铵离子;
ⅱ)可带有1-3个C1-C4烷基的C3-C8环烷基;
ⅲ)可带有1-5个卤原子和/或1个下列基团的C1-C8烷基:C1-C4烷氧基,C1-C4烷硫基,氰基,C1-C4烷基羰基,C3-C8环烷基,C1-C4烷氧基羰基,苯基,被卤原子、硝基、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基和/或C1-C4烷硫基取代的苯基,或者苯氧基;
ⅳ)可带有1-5个卤原子、并且带有1个下列基团的C1-C8烷基:含有1-3个氮原子的5元杂芳环,或者含有1个氮原子和1个氧或硫原子的5元杂芳环,这些杂芳环上可带有1-4个卤原子和/或1或2个下列基团:硝基,氰基,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基,和/或C1-C4烷硫基;
ⅴ)在2-位上带有1个下列基团的C2-C6烷基:C1-C4烷氧基亚氨基,C3-C6链烯基氧基亚氨基,C3-C6卤代链烯基氧基亚氨基,或苄氧基亚氨基;
ⅵ)C3-C6链烯基或C3-C6链炔基,这些基团上又可以带有1-5个卤原子;
ⅶ)可带有1-5个卤原子和/或1-3个下列基团的苯基:硝基,氰基,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基,和/或C1-C4烷硫基;
ⅷ)通过氮原子相连的5元杂芳环,它含有1-3个氮原子,并可带有1个或2个卤原子和/或1个或2个下列基团:硝基,氰基,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基,和/或C1-C4烷硫基;
式中,R10和R11是相同或不同的下列基团:
C1-C8烷基、C3-C6链烯基、C3-C6链炔基、C3-C8环烷基,这些基团上可带有C1-C4烷氧基、C1-C4烷硫基和/或苯基;
可被1个或多个下列基团取代的苯基:卤原子,硝基,氰基,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基,或C1-C4烷硫基;
或者R10和R11一起形成可带有1-3个C1-C4烷基的C3-C12亚烷基链;
g)或者R1为基团-NH-SO2-R12,式中的R12为:
C1-C4烷基、C3-C6链烯基、C3-C6链炔基、C3-CB环烷基,这些基团上还可以带有C1-C4烷氧基、C1-C4烷硫基和/或苯基;
可被1个或多个下列基团取代的苯基:卤原子,硝基,氰基,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基,或C1-C4烷硫基。
3.根据权利要求1的式Ⅰ所示3-卤-3-杂芳基羧酸衍生物,其中,R5是甲基,X是CH,R2和R3是甲氧基,并且Y、Z、R1和R4的定义同权利要求1。
4.根据权利要求1的式Ⅰ所示3-卤-3-杂芳基羧酸衍生物,其中,Z是氟原子,R5是甲基,X是CH,R2和R3是甲氧基,并且Y、R1和R4的定义同权利要求1。
5.含有权利要求1的式Ⅰ化合物和常规惰性添加剂的除草剂组合物。
6.一种控制不希望的植物生长的方法,它包括,使除草活性量的权利要求1的式Ⅰ化合物作用于植物上或它们的生长环境中。
7.一种影响植物生长的组合物,它含有权利要求1的式Ⅰ化合物和常规惰性添加剂。
8.一种调节植物生长的方法,它包括,使生物理调节量的权利要求1的式Ⅰ化合物作用于植物上或它们的生长环境中。
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CN94191870A Expired - Fee Related CN1072221C (zh) | 1993-04-23 | 1994-04-13 | 3-卤-3-杂芳基羧酸衍生物、制备它们的方法和中间体 |
Country Status (15)
Country | Link |
---|---|
US (1) | US5753594A (zh) |
EP (1) | EP0695302B1 (zh) |
JP (1) | JP3439476B2 (zh) |
KR (1) | KR100315611B1 (zh) |
CN (1) | CN1072221C (zh) |
AT (1) | ATE156822T1 (zh) |
AU (1) | AU6568094A (zh) |
BR (1) | BR9406358A (zh) |
CA (1) | CA2160803A1 (zh) |
DE (2) | DE4313411A1 (zh) |
ES (1) | ES2107211T3 (zh) |
HU (1) | HU215276B (zh) |
RU (1) | RU2146255C1 (zh) |
UA (1) | UA41930C2 (zh) |
WO (1) | WO1994025455A1 (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4441678A1 (de) * | 1994-11-23 | 1996-05-30 | Basf Ag | Derivate von alpha-Halogencarbonylverbindungen, Verfahren und Zwischenprodukte zu ihrer Herstellung |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2466451A1 (fr) * | 1979-09-27 | 1981-04-10 | Ayi Ayicoue | Derives monofluores en b homologues de l'acide lactique et de fluorocyanohydrines |
EP0347811A1 (en) * | 1988-06-20 | 1989-12-27 | Kumiai Chemical Industry Co., Ltd. | Alkanoic acid derivatives and herbicidal compositions |
CN1048852A (zh) * | 1989-07-19 | 1991-01-30 | 舍林股份公司 | 新的取代的α-嘧啶氧(硫)基-和α-三嗪氧(硫)基羧酸衍生物,它们的制备方法,以及它们作为除草剂,杀菌剂和植物生长调节剂的应用 |
DE4035758A1 (de) * | 1990-11-08 | 1992-05-14 | Schering Ag | Substituierte (alpha)-pyrimidinyloxy(thio)- und (alpha)-triazinyloxy(thio)-carbonsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider, fungizider und pflanzenwachstumsregulierender wirkung |
CN1067651A (zh) * | 1991-06-07 | 1993-01-06 | 宇部兴产株式会社 | 嘧啶或三嗪类衍生物、它们的制备方法和应用它们作为除草剂 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8912700D0 (en) * | 1989-06-02 | 1989-07-19 | Shell Int Research | Herbicidal compounds |
US5270289A (en) * | 1989-07-19 | 1993-12-14 | Schering Aktiengesellschaft | Herbicidal dimethoxy pyrimidinyloxy-fluorinated acids and salts |
CA2053603A1 (en) * | 1990-10-19 | 1992-04-20 | Katsumasa Harada | 3-alkoxyalkanoic acid derivative, process for preparing the same and herbicide using the same |
DE4142570A1 (de) * | 1991-12-21 | 1993-06-24 | Basf Ag | Glykolaldehyd- und milchsaeurederivate, deren herstellung und verwendung |
DE4313413A1 (de) * | 1993-04-23 | 1994-10-27 | Basf Ag | 3-(Het)aryloxy(thio)-Carbonsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung |
DE4332384A1 (de) * | 1993-09-23 | 1995-03-30 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten III |
-
1993
- 1993-04-23 DE DE4313411A patent/DE4313411A1/de not_active Withdrawn
-
1994
- 1994-04-13 AU AU65680/94A patent/AU6568094A/en not_active Abandoned
- 1994-04-13 CA CA002160803A patent/CA2160803A1/en not_active Abandoned
- 1994-04-13 EP EP94913587A patent/EP0695302B1/de not_active Expired - Lifetime
- 1994-04-13 RU RU95120095A patent/RU2146255C1/ru not_active IP Right Cessation
- 1994-04-13 KR KR1019950704619A patent/KR100315611B1/ko not_active IP Right Cessation
- 1994-04-13 HU HU9503037A patent/HU215276B/hu not_active IP Right Cessation
- 1994-04-13 ES ES94913587T patent/ES2107211T3/es not_active Expired - Lifetime
- 1994-04-13 UA UA95114908A patent/UA41930C2/uk unknown
- 1994-04-13 CN CN94191870A patent/CN1072221C/zh not_active Expired - Fee Related
- 1994-04-13 US US08/530,251 patent/US5753594A/en not_active Expired - Fee Related
- 1994-04-13 JP JP52381394A patent/JP3439476B2/ja not_active Expired - Fee Related
- 1994-04-13 WO PCT/EP1994/001140 patent/WO1994025455A1/de active IP Right Grant
- 1994-04-13 AT AT94913587T patent/ATE156822T1/de not_active IP Right Cessation
- 1994-04-13 BR BR9406358A patent/BR9406358A/pt not_active Application Discontinuation
- 1994-04-13 DE DE59403736T patent/DE59403736D1/de not_active Expired - Lifetime
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2466451A1 (fr) * | 1979-09-27 | 1981-04-10 | Ayi Ayicoue | Derives monofluores en b homologues de l'acide lactique et de fluorocyanohydrines |
EP0347811A1 (en) * | 1988-06-20 | 1989-12-27 | Kumiai Chemical Industry Co., Ltd. | Alkanoic acid derivatives and herbicidal compositions |
CN1048852A (zh) * | 1989-07-19 | 1991-01-30 | 舍林股份公司 | 新的取代的α-嘧啶氧(硫)基-和α-三嗪氧(硫)基羧酸衍生物,它们的制备方法,以及它们作为除草剂,杀菌剂和植物生长调节剂的应用 |
DE4035758A1 (de) * | 1990-11-08 | 1992-05-14 | Schering Ag | Substituierte (alpha)-pyrimidinyloxy(thio)- und (alpha)-triazinyloxy(thio)-carbonsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider, fungizider und pflanzenwachstumsregulierender wirkung |
CN1067651A (zh) * | 1991-06-07 | 1993-01-06 | 宇部兴产株式会社 | 嘧啶或三嗪类衍生物、它们的制备方法和应用它们作为除草剂 |
Also Published As
Publication number | Publication date |
---|---|
KR960701868A (ko) | 1996-03-28 |
HU9503037D0 (en) | 1995-12-28 |
HU215276B (hu) | 1998-11-30 |
UA41930C2 (uk) | 2001-10-15 |
RU2146255C1 (ru) | 2000-03-10 |
BR9406358A (pt) | 1996-02-13 |
ATE156822T1 (de) | 1997-08-15 |
KR100315611B1 (ko) | 2002-02-28 |
WO1994025455A1 (de) | 1994-11-10 |
EP0695302A1 (de) | 1996-02-07 |
EP0695302B1 (de) | 1997-08-13 |
DE4313411A1 (de) | 1994-10-27 |
JPH08509233A (ja) | 1996-10-01 |
US5753594A (en) | 1998-05-19 |
DE59403736D1 (de) | 1997-09-18 |
JP3439476B2 (ja) | 2003-08-25 |
CA2160803A1 (en) | 1994-11-10 |
AU6568094A (en) | 1994-11-21 |
CN1121716A (zh) | 1996-05-01 |
ES2107211T3 (es) | 1997-11-16 |
HUT73559A (en) | 1996-08-28 |
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