CN1314894A - 取代的苯基尿嘧啶类化合物 - Google Patents
取代的苯基尿嘧啶类化合物 Download PDFInfo
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- CN1314894A CN1314894A CN99810184.2A CN99810184A CN1314894A CN 1314894 A CN1314894 A CN 1314894A CN 99810184 A CN99810184 A CN 99810184A CN 1314894 A CN1314894 A CN 1314894A
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- Prior art keywords
- carbonyl
- group
- amino
- represent
- alkyl
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- 150000001875 compounds Chemical class 0.000 title claims description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 22
- 238000000034 method Methods 0.000 claims abstract description 35
- 238000002360 preparation method Methods 0.000 claims abstract description 26
- -1 formamyl Chemical group 0.000 claims description 221
- 239000000460 chlorine Substances 0.000 claims description 84
- 229910052801 chlorine Inorganic materials 0.000 claims description 82
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 79
- 239000011737 fluorine Substances 0.000 claims description 78
- 229910052731 fluorine Inorganic materials 0.000 claims description 78
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 65
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 49
- 239000001301 oxygen Substances 0.000 claims description 48
- 229910052760 oxygen Inorganic materials 0.000 claims description 48
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 41
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 39
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 35
- 229910052794 bromium Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 33
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 239000005864 Sulphur Substances 0.000 claims description 9
- 125000000638 benzylaminocarbonyl group Chemical group C(C1=CC=CC=C1)NC(=O)* 0.000 claims description 9
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 9
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 9
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- GLGSZERYOLHNML-UHFFFAOYSA-N $l^{1}-oxidanyl(phenyl)methanone Chemical compound [O]C(=O)C1=CC=CC=C1 GLGSZERYOLHNML-UHFFFAOYSA-N 0.000 claims description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- JSLZUBLGGPEVQN-DIPNUNPCSA-N (2r)-4-methyl-2-propan-2-yl-2-[2-[4-[4-[2-(3,4,5-trimethoxyphenyl)ethyl]piperazin-1-yl]butoxy]phenyl]-1,4-benzothiazin-3-one Chemical compound COC1=C(OC)C(OC)=CC(CCN2CCN(CCCCOC=3C(=CC=CC=3)[C@@]3(C(N(C)C4=CC=CC=C4S3)=O)C(C)C)CC2)=C1 JSLZUBLGGPEVQN-DIPNUNPCSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 4
- 230000002363 herbicidal effect Effects 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229950001891 iprotiazem Drugs 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- SETHSKIRVBKZTB-UHFFFAOYSA-N NC([O])=O Chemical compound NC([O])=O SETHSKIRVBKZTB-UHFFFAOYSA-N 0.000 claims description 3
- 150000001345 alkine derivatives Chemical class 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- BNSFIWAJTZNIHJ-UHFFFAOYSA-N CCN(CC)C([O])=O Chemical compound CCN(CC)C([O])=O BNSFIWAJTZNIHJ-UHFFFAOYSA-N 0.000 claims description 2
- LXRDMDPIACUDCG-UHFFFAOYSA-N CN(C)C([O])=O Chemical compound CN(C)C([O])=O LXRDMDPIACUDCG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 230000005611 electricity Effects 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 2
- 150000004692 metal hydroxides Chemical class 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
- 238000006722 reduction reaction Methods 0.000 claims description 2
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 35
- 150000002431 hydrogen Chemical class 0.000 claims 17
- 150000001721 carbon Chemical class 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000006309 butyl amino group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- DHQSPQHSZNOVQS-UHFFFAOYSA-N methylcarbamoyloxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(=O)NC DHQSPQHSZNOVQS-UHFFFAOYSA-N 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 4
- 239000000543 intermediate Substances 0.000 abstract description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 39
- 241000196324 Embryophyta Species 0.000 description 25
- 239000002994 raw material Substances 0.000 description 23
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 150000004702 methyl esters Chemical class 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 244000025254 Cannabis sativa Species 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000004176 ammonification Methods 0.000 description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 230000008029 eradication Effects 0.000 description 3
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000010902 straw Substances 0.000 description 3
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 description 2
- IBXNCJKFFQIKKY-UHFFFAOYSA-N 1-pentyne Chemical compound CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 description 2
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- ABOOPXYCKNFDNJ-UHFFFAOYSA-N 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-UHFFFAOYSA-N 0.000 description 2
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
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- PVSGXWMWNRGTKE-UHFFFAOYSA-N 5-methyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=C(C)C=C1C(O)=O PVSGXWMWNRGTKE-UHFFFAOYSA-N 0.000 description 2
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
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- 244000075850 Avena orientalis Species 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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- 239000005531 Flufenacet Substances 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 244000017020 Ipomoea batatas Species 0.000 description 2
- 235000002678 Ipomoea batatas Nutrition 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241000209510 Liliopsida Species 0.000 description 2
- 241000209117 Panicum Species 0.000 description 2
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 2
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
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- 239000002420 orchard Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 1
- 239000011146 organic particle Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- IOXAXYHXMLCCJJ-UHFFFAOYSA-N oxetan-3-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC2COC2)=N1 IOXAXYHXMLCCJJ-UHFFFAOYSA-N 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
- JZPKLLLUDLHCEL-UHFFFAOYSA-N pentoxazone Chemical compound O=C1C(=C(C)C)OC(=O)N1C1=CC(OC2CCCC2)=C(Cl)C=C1F JZPKLLLUDLHCEL-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 1
- OTYNBGDFCPCPOU-UHFFFAOYSA-N phosphane sulfane Chemical compound S.P[H] OTYNBGDFCPCPOU-UHFFFAOYSA-N 0.000 description 1
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 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
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- OYJMHAFVOZPIOY-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 OYJMHAFVOZPIOY-UHFFFAOYSA-N 0.000 description 1
- FKLQIONHGSFYJY-UHFFFAOYSA-N propan-2-yl 5-[4-bromo-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]-2-chloro-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(C=2C(=C(N(C)N=2)C(F)(F)F)Br)=C1F FKLQIONHGSFYJY-UHFFFAOYSA-N 0.000 description 1
- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- YXIIPOGUBVYZIW-UHFFFAOYSA-N pyraflufen Chemical compound ClC1=C(OC(F)F)N(C)N=C1C1=CC(OCC(O)=O)=C(Cl)C=C1F YXIIPOGUBVYZIW-UHFFFAOYSA-N 0.000 description 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- DEIKMOQTJBGGAX-DJKKODMXSA-N pyriminobac Chemical compound CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(O)=O DEIKMOQTJBGGAX-DJKKODMXSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 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
- 239000003516 soil conditioner Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 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
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/90—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. amino-diphenylethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
- C07C255/59—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/48—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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 with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
- C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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 with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid
Abstract
本发明涉及新的通式(Ⅰ)的取代的苯基尿嘧啶,其中n、Q、R1、R2、R3、R4、R5和X具有说明书中给出的含义。本发明还涉及制备所述的取代的苯基尿嘧啶的方法和新中间体以及其作为除草剂的应用。
Description
本发明涉及新颖的取代的苯基尿嘧啶类化合物,涉及它们的制备和新的中间体及其它们作为除草剂的应用。
某些取代的芳基尿嘧啶类业已公开于(专利)文献中(参见EP-A-255047、EP-A-260621、EP-A-408382、EP-A-438209、EP-A-473551、EP-A-517181、EP-A-563384、WO-A-91/00278、WO-A-91/07393、WO-A-93/14073、WO-A-98/41093、US-A-4979982、US-A-5084084、US-A-5127935、US-A-5154755、US-A-5169430、US-A-5486610、US-A-5356863)。然而,这些化合物迄今未获得任何特别的重要性。
因此,本发明提供新颖的通式(Ⅰ)的取代的苯基尿嘧啶类化合物其中n代表数字0、1、2、3、4或5,Q 代表O(氧)、S(硫)、SO、SO2、NH或N(烷基),R1 代表氢、氨基或任选被取代的烷基,R2 代表羧基、氰基、氨基甲酰基、硫代氨基甲酰基或代表各任选被
取代的烷基或烷氧基羰基,R3 代表氢、卤素或任选被取代的烷基,R4 代表氢、氰基、氨基甲酰基、硫代氨基甲酰基或卤素,R5 代表氰基、氨基甲酰基、硫代氨基甲酰基、卤素,或代表各任选
被取代的烷基或烷氧基,和X 代表羟基、巯基、氨基、硝基、氰基、羧基、氨基甲酰基、硫代
氨基甲酰基、卤素,或代表各任选被取代的烷基、烷氧基、烷硫
基、烷基亚磺酰基、烷基磺酰基、烷基氨基、二烷基氨基、烷基
羰基、烷氧基羰基、烷基氨基羰基、二烷基氨基羰基、烷基羰氧
基、烷氧基羰氧基、烷基氨基羰氧基、二烷基氨基羰氧基、苯基
羰氧基、烷基羰基氨基、烷氧基羰基氨基、烷基磺酰基氨基、链
烯基、链烯氧基、链烯氧基羰基、炔基、炔氧基或炔氧基羰基,
其中在n大于1的情况下,X在每一可能的化合物中也可以是不
同的上述基团。
在上述定义中,烃链如烷基-以及在与杂原子相连时,如在烷氧基中-各是直链或支链。
只要本发明通式(Ⅰ)化合物含有不对称取代的碳原子,本发明就还涉及各R对映体和S-对映体以及这些对映体的任何混合物,特别是外消旋体。n 优选代表数字0、1、2、3或4;Q 优选代表O(氧)、S(硫)、SO、SO2、NH或N(C1-C4-烷基);R1 优选代表氢、氨基或任选由氰基、羧基、氟、氯、C1-C4-烷氧基
或C1-C4-烷氧基羰基取代的C1-C4-烷基;R2 优选代表羧基、氰基、氨基甲酰基、硫代氨基甲酰基,或代表C1-C4-
烷基或C1-C4-烷氧基羰基,它们各任选由氰基、氟、氯或C1-C4-
烷氧基取代;R3 优选代表氢、氟、氯、溴,或代表任选由氟或氯取代的C1-C4-烷
基;R4 优选代表氢、氰基、氨基甲酰基、硫代氨基甲酰基、氟、氯或溴;R5 优选代表氰基、氨基甲酰基、硫代氨基甲酰基、氟、氯、溴,或
代表C1-C4-烷基或C1-C4-烷氧基,它们各任选由氟和/或氯取代;
和X 优选代表羟基、巯基、氨基、硝基、氰基、羧基、氨基甲酰基、
硫代氨基甲酰基、氟、氯、溴、碘,或代表烷基、烷氧基、烷硫
基、烷基亚磺酰基、烷基磺酰基或烷基氨基,它们各具有1至6
个碳原子且各任选由羟基、氰基、羧基、氨基甲酰基、氟、氯、
C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基
磺酰基、C1-C4-烷基羰基、C1-C4-烷氧基羰基、C2-C4-链烯氧基羰
基、C2-C4-炔氧基羰基、C1-C4-烷基氨基羰基、二(C1-C4-烷基)氨
基-羰基、苯氧基羰基、苄氧基羰基、苯基氨基羰基或苄基氨基
羰基取代,或代表在烷基基团中各具有1至6个碳原子的二烷基
氨基,或代表烷基羰基、烷氧基羰基、烷基氨基羰基、烷基羰氧
基、烷氧基羰氧基或烷基氨基羰氧基,它们在烷基基团中各具有
1至6个碳原子且它们各任选由氰基、氟、氯、溴或C1-C4-烷氧
基取代,或代表二烷基氨基羰基或二烷基氨基羰氧基,它们在烷
基基团中各具有1至6个碳原子,或代表苯基羰氧基,或代表烷
基羰基氨基、烷氧基羰基氨基、烷基磺酰基氨基,它们各任选由
氟、氯或溴取代,或代表链烯基、链烯氧基、链烯氧基羰基、炔
基、炔氧基或炔氧基羰基,它们各具有至多6个碳原子且它们各
任选由氰基、羧基、氟、氯、溴或C1-C4-烷氧基-羰基取代;n 特别优选代表数字1、2或3;Q 特别优选代表O(氧)、S(硫)、SO、SO2、NH或N(甲基);R1 特别优选代表氢、氨基,或代表甲基、乙基、正或异丙基,它们
各任选由氰基、氟、氯、甲氧基或乙氧基取代;R2 特别优选代表羧基、氰基、氨基甲酰基、硫代氨基甲酰基,或代
表甲基、乙基、正或异丙基、甲氧基羰基、乙氧基羰基、正或异
丙氧基羰基,它们各任选由氰基、氟、氯、甲氧基或乙氧基取代;R3 特别优选代表氢、氟、氯、溴,或代表甲基或乙基,它们各任选
由氟和/或氯取代;R4 特别优选代表氢、氟或氯;R5 特别优选代表氰基、氨基甲酰基、硫代氨基甲酰基、氟、氯、溴、
甲基或三氟甲基;X 特别优选代表羟基、巯基、氨基、硝基、氰基、羧基、氨基甲酰
基、硫代氨基甲酰基、氟、氯、溴,或代表甲基、乙基、正或异
丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正或异丙氧
基、正-、异-、仲-或叔丁氧基、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、乙基磺酰基、
甲基氨基、乙基氨基、正或异丙基氨基、正-、异-、仲-或叔丁
基氨基,它们各任选由氰基、羧基、氨基甲酰基、氟、氯、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、乙基磺酰基、乙酰
基、丙酰基、正或异丁酰基、甲氧基羰基、乙氧基羰基、正或异
丙氧羰基、烯丙氧基羰基、1-丁烯-3-基氧基羰基、2-丁烯-4-
基氧基羰基、炔丙基氧基羰基、1-丁炔-3-基氧基羰基、2-丁炔
-4-基氧基羰基、甲基氨基羰基、乙基氨基羰基、正或异丙基氨
基羰基、二甲基氨基羰基、二乙基氨基羰基、苯氧基羰基、苄氧
基羰基、苯基氨基羰基或苄基氨基羰基取代,或代表二甲基氨基
或二乙基氨基,或代表乙酰基、丙酰基、正或异丁酰基、甲氧基
羰基、乙氧基羰基、正或异丙氧基羰基、甲基氨基羰基、乙基氨
基羰基、正或异丙基氨基羰基、乙酰氧基、丙酰氧基、正或异丁
酰氧基、甲氧基羰氧基、乙氧基羰氧基、正或异丙氧基羰氧基、
甲基氨基羰氧基、乙基氨基羰氧基、正或异丙基氨基羰氧基,它
们各任选由氰基、氟、氯、甲氧基、乙氧基、正或异丙氧基取代,
或代表二甲基氨基羰基、二乙基氨基羰基、二甲基氨基羰氧基或
二乙基氨基羰氧基,或代表苯基羰氧基,或代表乙酰基氨基、丙
酰基氨基、正或异丁酰基氨基、甲氧基羰基氨基、乙氧基羰基氨
基、正或异丙氧基羰基氨基、甲基磺酰基氨基、乙基磺酰基氨基、
正或异丙基磺酰基氨基、正-、异-、仲-或叔丁基磺酰基氨基,
它们各任选由氟或氯取代,或代表乙烯基、丙烯基、丙烯氧基、
丙烯氧基羰基、乙炔基、丙炔基、丙炔氧基或丙炔氧基羰基,它
们各任选由氰基、羧基、氟、氯、甲氧基羰基或乙氧基羰基取代。
根据本发明优选的是其中存在上面提到的优选含义组合的式(Ⅰ)化合物。
根据本发明特别优选的是其中存在上面提到的特别优选含义组合的式(Ⅰ)化合物。
非常特别优选是式(ⅠA)化合物其中R1 代表氢、氨基或甲基,R2 代表三氟甲基、一氯二氟甲基、二氟甲基或五氟乙基,R3 代表氢、氯或甲基,R4 代表氢、氟或氯,R5 代表氰基或硫代氨基甲酰基,和X 代表羟基、巯基、氨基、硝基、氰基、羧基、氨基甲酰基、硫代
氨基甲酰基、氟、氯、溴,或代表甲基、乙基、甲氧基、乙氧基、
甲硫基、乙硫基、甲氧基羰基或乙氧基羰基,它们各任选由氰基、
羧基、氨基甲酰基、氟、氯、甲氧基、乙氧基、正或异丙氧基、
甲氧基羰基、乙氧基羰基、正或异丙氧基羰基、烯丙氧基羰基、
炔丙氧基羰基、1-丁烯-3-基氧基羰基、2-丁烯-4-基氧基羰基、
炔丙氧基羰基、1-丁炔-3-基氧基羰基、2-丁炔-4-基氧基羰基、
甲基氨基羰基、乙基氨基羰基、正或异丙基氨基羰基、二甲基氨
基羰基、二乙基氨基羰基、苯氧基羰基、苄氧基羰基、苯基氨基
羰基或苄基氨基羰基取代,或代表由甲氧基羰基或乙氧基羰基取
代的乙烯基。
另一组非常特别优选的是式(ⅠA)化合物,其中R1 代表甲基,R2 代表三氟甲基、一氯二氟甲基、二氟甲基或五氟乙基,R3 代表氢、氯或甲基,R4 代表氢、氟或氯,R5 代表氟、氯、溴或三氟甲基,和X 代表羟基、巯基、氨基、硝基、氰基、羧基、氨基甲酰基、硫代
氨基甲酰基、氟、氯、溴,或代表甲基、乙基、甲氧基、乙氧基、
甲硫基、乙硫基、甲氧基羰基或乙氧基羰基,它们各任选由氰基、
羧基、氨基甲酰基、氟、氯、甲氧基、乙氧基、正或异丙氧基、
甲氧基羰基、乙氧基羰基、正或异丙氧基羰基、烯丙氧基羰基、
炔丙氧基羰基、1-丁烯-3-基氧基羰基、2-丁烯-4-基氧基羰基、
炔丙氧基羰基、1-丁炔-3-基氧基羰基、2-丁炔-4-基氧基羰基、
甲基氨基羰基、乙基氨基羰基、正或异丙基氨基羰基、二甲基氨
基羰基、二乙基氨基羰基、苯氧基羰基、苄氧基羰基、苯基氨基
羰基或苄基氨基羰基取代,或代表由甲氧基羰基或乙氧基羰基取
代的乙烯基。
另一组非常特别优选的是式(ⅠA)化合物,其中R1 代表氢、氨基或甲基,R2 代表羧基、氰基、氨基甲酰基、硫代氨基甲酰基、甲氧基羰基或
乙氧基羰基,R3 代表氢、氯或甲基,R4 代表氢、氟或氯,R5 代表氰基、硫代氨基甲酰基、氟、氯、溴或三氟甲基,和X 代表羟基、巯基、氨基、硝基、氰基、羧基、氨基甲酰基、硫代
氨基甲酰基、氟、氯、溴,或代表甲基、乙基、甲氧基、乙氧基、
甲硫基、乙硫基、甲氧基羰基或乙氧基羰基,它们各任选由氰基、
羧基、氨基甲酰基、氟、氯、甲氧基、乙氧基、正或异丙氧基、
甲氧基羰基、乙氧基羰基、正或异丙氧基羰基、烯丙氧基羰基、
炔丙氧基羰基、1-丁烯-3-基氧基羰基、2-丁烯-4-基氧基羰基、
炔丙氧基羰基、1-丁炔-3-基氧基羰基、2-丁炔-4-基氧基羰基、
甲基氨基羰基、乙基氨基羰基、正或异丙基氨基羰基、二甲基氨
基羰基、二乙基氨基羰基、苯氧基羰基、苄氧基羰基、苯基氨基
羰基或苄基氨基羰基取代,或代表由甲氧基羰基或乙氧基羰基取
代的乙烯基。
上面提到的一般或优选的基团定义适合于式(Ⅰ)终产物,且相应地,也适合于在每一种制备情况下所需的起始原料或中间体。这些基团定义可以按照需要相互结合,即,包括上面提到的优选范围间的组合。
本发明通式(Ⅰ)化合物的实例分组列于下文。
组1Xn具有下文给出的含义:2-羟基、3-羟基、4-羟基、2-氰基、3-氰基、4-氰基、2-羧基、3-羧基、4-羧基、2-氟、3-氟、4-氟、2,3-二氟、2,4-二氟、2,5-二氟、2,6-二氟、3,4-二氟、3,5-二氟、2-氯、3-氯、4-氯、2,3-二氯、2,4-二氯、2,5-二氯、2,6-二氯、3,4-二氯、3,5-二氯、2-溴、3-溴、4-溴、2-甲基、3-甲基、4-甲基、2,3-二甲基、2,4-二甲基、2,5-二甲基、2,6-二甲基、3,4-二甲基、3,5-二甲基、2-三氟甲基、3-三氟甲基、4-三氟甲基、2-甲氧基、3-甲氧基、4-甲氧基、2,4-二甲氧基、2,5-二甲氧基、2,6-二甲氧基、3,4-二甲氧基、2-二氟甲氧基、4-二氟甲氧基、2-三氟甲氧基、4-三氟甲氧基、4-乙氧基、4-甲硫基、4-乙硫基、4-甲氧基羰基、4-乙氧基羰基、羧基甲氧基、4-甲氧基羰基甲氧基、4-乙氧基羰基甲氧基、4-正丙氧基羰基甲氧基、4-异丙氧基羰基甲氧基、4-(1-羧基乙氧基)、4-(1-(甲氧基羰基)乙氧基)、4-(1-(乙氧基羰基)乙氧基)、4-(1-(正丙氧基羰基)乙氧基)、4-(1-(异丙氧基羰基)乙氧基)、4-(烯丙氧基羰基甲氧基)、4-(1-(烯丙氧基羰基)乙氧基)、4-(炔丙氧基羰基甲氧基)、4-(1-(炔丙氧基羰基)乙氧基)、4-(苄氧基羰基甲氧基)、4-(1-(苄氧基羰基)乙氧基)、4-(氨基羰基甲氧基)、4-(甲基氨基羰基甲氧基)、4-(乙基氨基羰基甲氧基)、4-(正丙基氨基羰基甲氧基)、4-(异丙基氨基羰基甲氧基)、4-(二甲基氨基羰基甲氧基)、4-(1-(甲基氨基羰基)乙氧基)、4-(1-(乙基氨基羰基)乙氧基)、4-(1-(正丙基氨基羰基)乙氧基)、4-(1-(异丙基氨基羰基)乙氧基)、4-(1-(二甲基氨基羰基)乙氧基)、4-(2-甲氧基羰基-乙烯基)、4-(2-乙氧基羰基-乙烯基)。
组2Xn具有组1中给出的含义。
组5Xn具有组1中给出的含义。
组8Xn具有组1中给出的含义。
新颖的通式(Ⅰ)的取代的苯基尿嘧啶具有令人感兴趣的生物性能。特别是它们具有强的除草活性。
新颖的通式(Ⅰ)的取代的氨基苯基尿嘧啶如下获得:(a)如果适合在反应辅助剂存在下和如果适合在稀释剂存在下,使通式(Ⅱ)的卤代苯基尿嘧啶其中R1、R2、R3、R4和R5如上所定义,和X1 代表卤素,与通式(Ⅲ)的芳基化合物
其中
其中
R2和R3具有上面提到的含义,和
R 代表烷基、芳基或芳基烷基,与通式(Ⅴ)的芳基异氰酸酯
其中
n、Q、R4、R5和X具有上面提到的含义,或通式(Ⅳ)的芳基尿烷(芳基氨基甲酸酯)反应
其中
n、Q、R4、R5和X具有上面提到的含义,
R 代表烷基、芳基或芳基烷基,或(c)在水存在下和如果适宜在有机溶剂存在下,使通式(Ⅶ)的N-芳基-1-烷氧基羰基氨基-马来酰亚胺
其中
n、Q、R3、R4、R5和X具有上面提到的含义和
其中
n、Q、R2、R3、R4、R5和X具有上面提到的含义与1-氨基氧基-2,4-二硝基-苯或通式(Ⅷ)的烷基化试剂反应
X2-A1 (Ⅷ)
其中
A1 代表任选被取代的烷基和
X2 代表卤素或基团-O-SO2-O-A1,且,如果适宜,随后用常规方式在取代基定义的范围内进行亲电或亲核和/或氧化或还原反应。
通式(Ⅰ)的化合物可以用常规方法转化成具有上面定义的其它通式(Ⅰ)化合物,例如通过酯化或水解(例如X:OCH2COOH→OCH2COOC2H5、OCH(CH3)COOCH3→OCH(CH3)COOH),与氰气或硫化氢反应(例如R5:Br→CN,CN→CSNH2),羧基化合物用常规方法转化成其它羧酸衍生物(例如,R2:COOH→CN,CN→CSNH2,COOH→COOCH3,COOCH3→CONH2);参见制备实施例)。
使用,例如,1-(4-氰基-2,5-二氟苯基)-4-氯二氟甲基-3,6-二氢-2,6-二氧代-1(2H)-嘧啶和1-(4-羟基-苯氧基)丙酸乙酯作为起始原料,本发明方法(a)的反应途径可以用下列反应式来说明:
使用,例如,1-[2-氯-4-三氟甲基-5-(4-甲氧基羰基甲氧基苯氧基)苯基]-4-二氟甲基-3,6-二氢-2,6-二氧代-1(2H)-嘧啶和甲基溴作为起始原料,本发明方法(d)的反应途径可以用下列反应式来说明:
式(Ⅱ)提供在制备本发明式(Ⅰ)化合物的本发明方法(a)中用作起始原料的卤代苯基尿嘧啶的一般定义。在式(Ⅱ)中,R1、R2、R3、R4和R5各特别具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的R1、R2、R3、R4和R5的优选、特别优选或非常特别优选的含义。X1优选代表氟或氯,尤其是氟。
式(Ⅱ)起始原料是已知的和/或可以通过已知的方法制备(参见,EP-A-648749)。
通式(Ⅲ)提供在本发明方法(a)中另一用作起始原料的取代的芳基化合物的一般定义。在式(Ⅲ)中,n、Q和X各特别具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的n、Q和X的优选、特别优选或非常特别优选的含义。
式(Ⅲ)起始原料是有机合成上已知的化学品。
式(Ⅳ)提供在制备本发明式(Ⅰ)化合物的本发明方法(b)中用作起始原料的氨基烯酸酯的一般定义。在式(Ⅳ)中,R2和R3各特别具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的R2和R3的优选、特别优选的或非常特别优选含义;R优选代表C1-C4-烷基、苯基或苄基,特别是甲基或乙基。
式(Ⅳ)起始原料是已知的和/或可以通过已知的方法制备(参见,杂环有机化学杂志,9(1972),513-522)。
通式(Ⅴ)提供在本发明方法(b)中另一用作起始原料的芳基异氰酸酯的一般定义。在式(Ⅴ)中,n、Q、R4、R5和X各特别具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的n、Q、R4、R5和X的优选、特别优选或非常特别优选的含义。
式(Ⅴ)起始原料是迄今未知的;作为新物质,它们也是本发明申请的主题。
其中
n、Q、R4、R5和X具有上面提到的含义,与光气在稀释剂例如氯苯存在下在-20℃至+150℃的温度下反应(参见,例如,同样是EP-A-648749)。
通式(Ⅵ)提供在本发明方法(b)中任选用作起始原料的芳基尿烷的一般定义。在式(Ⅵ)中,n、Q、R4、R5和X各特别具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的n、Q、R4、R5和X的优选、特别优选或非常特别优选的含义;R优选代表C1-C4-烷基、苯基或苄基,特别是甲基或乙基。
式(Ⅵ)起始原料是迄今未知的;作为新物质,它们也是本发明申请的主题。
其中
n、Q、R4、R5和X具有上面提到的含义与通式(Ⅹ)的氯代羰基化合物反应
RO-CO-Cl (Ⅹ)
其中
R具有上面提到的含义,如果适宜在酸受体如吡啶存在下,和如果适宜在稀释剂如二氯甲烷存在下,在-20℃至+100℃的温度下进行反应(参见,例如制备实施例)。
需作为前体的通式(Ⅸ)的苯胺衍生物是已知的和/或可以通过本身已知的方法制备(参见,Justus Liebigs Ann.Chem.740(1970),169-179;US-A-3715395;US-A-3914418;DE-A-2748554;DE3736089)。
其中
n、R4和X具有上面提到的含义和
Y代表氰基、硫代氨基甲酰基或三氟甲基,是迄今未知的,也是新物质,是本发明申请的主题。
新的通式(Ⅸa)苯胺衍生物如下获得使通式(Ⅺ)的苯胺
其中
其中
n、Q和X具有上面提到的含义或通式(Ⅲ)的金属化合物如果适宜在反应辅助剂如氢化钠存在下和如果适宜在稀释剂如N-甲基吡咯烷酮存在下在0℃至150℃的温度下进行反应(参见,例如制备实施例)。
通式(Ⅶ)提供在本发明方法(c)中用作起始原料的N-芳基-1-烷氧基-羰基氨基马来酰亚胺的一般定义。在式(Ⅶ)中,n、Q、R3、R4、R5和X各特别具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的n、Q、R3、R4、R5和X的优选、特别优选或非常特别优选的含义;R4优选代表C1-C4-烷基,特别是甲基或乙基。
新的通式(Ⅶ)的N-芳基-1-烷氧基羰基氨基-马来酰亚胺如下获得:使通式(Ⅻ)的(2,5-二氧代-2,5-二氢-呋喃-3-基)-氨基甲酸烷基酯
其中
R3 具有上面提到的含义,和
其中
n、Q、R4、R5和X具有上面提到的含义,如果适宜在稀释剂如乙酸存在下,在0℃至200℃、优选在50℃至150℃的温度下进行反应。
通式(Ⅻ)的前体是已知的和/或可以用本身已知的方法制备(参见,例如DE19604229)。
通式(Ⅰa)提供在本发明方法(d)中用作起始原料的取代的苯基尿嘧啶的一般定义。在式(Ⅰa)中,n、Q、R2、R3、R4、R5和X各特别具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的n、Q、R2、R3、R4、R5和X的优选、特别优选或非常特别优选的含义。
作为新物质,用于方法(b)的通式(Ⅰa)起始原料也同样是本发明申请的主题;它们可以通过本发明方法(a)、(b)和(c)制备。
通式(Ⅷ)提供在本发明方法(d)中另一用作起始原料的烷基化试剂的一般定义。在式(Ⅷ)中,A1优选代表任选由氰基、卤素或C1-C4-烷氧基取代的具有1至4个碳原子的烷基,和X2优选代表氯、溴、碘、甲基磺酰氧基或乙基磺酰氧基;特别是,A1代表甲基、乙基、正或异丙基,它们各任选由氰基、氟、氯、甲氧基或乙氧基取代,和X2代表氯、溴、碘、甲基磺酰氧基或乙基磺酰氧基。
式(Ⅷ)原料是有机合成中已知的化学品。
制备通式(Ⅰ)化合物的本发明方法优选使用稀释剂进行。适合于进行本发明方法(a)、(b)、(c)和(d)的稀释剂除了水之外特别是惰性有机溶剂。这些溶剂包括特别是脂肪族、脂环族或芳族的任选卤代的烃,诸如,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、异丙醚、二噁烷、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、丙腈或丁腈;酰胺类,如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酰三胺;酯类,如乙酸甲酯或乙酸乙酯;亚砜类,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、二甘醇单甲醚、二甘醇单乙醚,它们与水的混合物,或纯水。
适合于本发明方法(a)、(b)、(c)和(d)的反应辅助剂通常是常规的无机或有机碱或酸受体。这些物质优选包括碱金属或碱土金属的乙酸盐、氨化物、碳酸盐、碳酸氢盐、氢化物、氢氧化物或醇盐,如乙酸钠、乙酸钾或乙酸钙、氨化锂、氨化钠、氨化钾或氨化钙、碳酸钠、碳酸钾或碳酸钙、碳酸氢钠、碳酸氢钾或碳酸氢钙、氢化锂、氢化钠、氢化钾或氢化钙、氢氧化锂、氢氧化钠、氢氧化钾或氢氧化钙,甲醇、乙醇、正或异丙醇、正-、异-、仲-或叔丁醇的钠盐或甲醇、乙醇、正-或异丙醇、正-、异-、仲-或叔丁醇的钾盐;另外还有碱性有机氮化合物,如,三甲胺、三乙胺、三丙胺、三丁胺、乙基-二异丙基胺、N,N-二甲基-环己基胺、二环己基胺、乙基-二环己基胺、N,N-二甲基苯胺、N,N-二甲基-苄基胺、吡啶,2-甲基-、3-甲基-、4-乙基-、2,4-二甲基-、2,6-二甲基-、3,4-二甲基-和3,5-二甲基-吡啶、5-乙基-2-甲基-吡啶、4-二甲基氨基-吡啶、N-甲基-哌啶、1,4-二氮杂二环[2,2,2]-辛烷(DABCO)、1,5-二氮杂二环[4,3,0]-壬-5-烯(DBN)或1,8-二氮杂二环[5,4,0]-十一-7-烯(DBU)。
其它用于本发明方法的反应辅助剂是相转移催化剂。这些催化剂可以提到的实例有:
四丁基溴化铵、四丁基氯化铵、四辛基氯化铵、四丁基硫酸氢铵、甲基三辛基氯化铵、十六烷基三甲基氯化铵、十六烷基三甲基溴化铵、苄基三甲基氯化铵、苄基三乙基氯化铵、苄基三甲基氢氧化铵、苄基三乙基氢氧化铵、苄基三丁基氯化铵、苄基三丁基溴化铵、四丁基溴化鏻、四丁基氯化鏻、三丁基十六烷基溴化鏻、丁基三苯基氯化鏻、乙基三辛基溴化鏻、四苯基溴化鏻。
进行本发明方法(a)、(b)、(c)和(d)时,反应温度可以在相对宽的范围内变化。通常,反应是在0℃至150℃、优选在10℃至120℃间的温度下进行。
本发明的方法通常是在常压下进行的。然而,本发明方法也可以在加压或减压下——通常是在0.1巴至10巴间的压力下进行。
进行本发明方法时,通常采用大致等摩尔量的起始原料。然而,也可以相对大地过量采用反应组分之一。反应通常是在适合的稀释剂中在反应辅助剂存在下进行的,且反应混合物通常在所需的温度下搅拌数小时。后处理是用常规方法进行(参见,制备实施例)。
本发明活性化合物可以用作脱叶剂、干燥剂、杀茎杆剂,和特别是用作除草剂。所谓的杂草,就其最广义而言,应理解为生长在不该生长的地方的所有植物。本发明的物质是作为灭生性除草剂或是选择性除草剂基本上取决于所用的量。
本发明化合物可以与例如下列植物相关使用:
下列属的双子叶杂草:芥属、独行草属、猪殃殃属、繁缕属、母菊属、春黄菊属、牛膝属、藜属、荨麻属、千里光属、苋属、马齿苋属、苍耳属、旋花属、甘薯属、蓼属、田菁属、豚草属、蓟属、飞廉属、苦苣菜属、茄属、焊菜属、节节草属、母草属、野芝麻属、婆婆纳属、苘麻属、刺酸模属、曼陀罗属、堇菜属、鼬瓣花属、罂粟属、矢车菊属、三叶草属、毛茛属和蒲公英属,
下列属的双子叶作物:棉属、大豆属、甜菜属、胡萝卜属、菜豆属、豌豆属、茄属、亚麻属、甘薯属、巢菜属、烟草属、蕃茄属、花生属、芸苔属、莴苣属、黄瓜属和南瓜属,
下列属的单子叶杂草:稗属、狗尾草属、黍属、马唐属、梯牧草属、早熟禾属、羊茅属、蟋蟀草属、臂形草属、黑麦草属、雀麦属、燕麦属、莎草属、高梁属、冰草属、狗牙根属、雨久花属、飘拂草属、慈菇属、荸荠属、藨草属、雀稗属、鸭嘴草属、尖瓣花属、龙爪茅属、剪股颖属、看麦娘属和风草属,
下列属的单子叶作物:稻属、玉米属、小麦属、大麦属、燕麦属、黑麦属、高梁属、黍属、甘蔗属、凤梨属、天门冬属和葱属。
然而,本发明活性化合物的应用决不限于这些属,且也可以相同的方式延伸至其它植物。
取决于化合物的浓度,化合物适合于灭生性防治杂草,例如工业地域和铁道线,以及有或无种植树林的道路和广场。同样,化合物可以用于防治多年生作物中的杂草,例如森林、装饰树林、果园、葡萄园、柑桔林、坚果园、蕉种植园、咖啡种植园、茶园、橡胶种植园、油棕榈种植园、可可种植园、软果林和啤酒花田、草场、体育场和牧场中的杂草。且本发明化合物还可以用于选择性地防治一年生作物中的杂草。
本发明式(Ⅰ)化合物当施用于土壤和植物的地上部分时显示出强的除草活性和宽的作用谱。在某种程度上,它们还适合于以芽前和芽后二种方式选择性地防治单子叶和双子叶作物中的单子叶和双子叶杂草。
活性化合物可以转化成常规的制剂,如溶液、乳剂、可湿性粉剂、悬浮剂、粉剂、粉尘剂、膏剂、可溶性粉剂、颗粒剂、悬乳剂、用活性化合物浸渍的天然或合成材料,以及包在聚合物中的微细胶囊。
这些制剂可以用已知的方式生产,例如,将活性化合物与扩充剂,即液体和/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。
在用水作扩充剂的情况下,也可以用有机溶剂作助溶剂。适合的液体溶剂主要有: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,例如石油馏份、矿物和植物油,醇类,如丁醇或二醇以及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺和二甲基亚砜,以及水。
适合的固体载体是:例如铵盐和磨碎的天然矿物质,如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐,适合用于颗粒剂的固体载体有:例如压碎并分级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;适合的乳化剂和/或起泡剂是:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及白蛋白水解产物;适合的分散剂是: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羧甲基纤维素和粉状、颗粒或乳胶形式的天然和合成聚合物,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。其它的添加剂可以是矿物油和植物油。
也可以使用着色剂,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,和微量营养元素如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中通常含有按重量计0.1至95%的活性化合物,优选0.5至90%。
为防治杂草,本发明活性化合物,其原样或以其制剂形式,也可以作为与已知除草剂一起的混合物使用,可以是终制剂或桶混物。
混合物的可能的共组分是已知除草剂,例如,乙草胺、三氟羧草醚(钠盐)、苯草醚、甲草胺、禾草灭(钠盐)、莠灭净、amidochlor、酰嘧黄隆、莎稗磷、磺草灵、azafenidin、莠去津、四唑嘧黄隆、草除灵、呋草黄、苄嘧黄隆(甲酯)、灭草松、吡草酮、新燕灵(乙酯)、双丙氨酰磷、甲羧除草醚、双草醚、溴丁酰草胺、溴酚肟、溴苯腈、丁草胺、丁草特、cafenstrole、caloxydim、双酰草胺、carfentrazone(-ethyl)、甲氧除草醚、草灭畏、杀草敏、氯嘧黄隆(乙酯)、草枯醚、绿黄隆、绿麦隆、cinidon(-ethyl)、环庚草醚、醚黄隆、烯草酮、炔草酸、异噁草酮、氯甲酰草胺、二氟吡啶酸、clopyrasulfuron(-ethyl)、cloransulam(-methyl)、cumyluron、氰草津、cybutryne、灭草特、环丙嘧磺隆、噻草酮、氰氟草酯、2,4-滴、2,4-滴丁酸、2,4-滴丙酸、甜菜安、燕麦敌、麦草畏、禾草灵(甲酯)、diclosulam、乙酰甲草胺、野燕枯、吡氟草胺、diflufenzopyr、唑隆、哌草丹、二甲草胺、二甲丙乙净、二甲吩草胺、dimexyflam、氨氟灵、双苯酰草胺、敌草快、氟硫草定、敌草隆、杀草隆、epoprodan、茵达灭、戊草丹、乙丁烯氟灵、胺苯黄隆(甲酯)、乙呋草黄、ethoxyfen、ethoxysulfuron、etobenzanid、噁唑禾草灵乙酯、麦草伏(异丙酯)、麦草伏(异丙酯-L)、麦草伏(甲酯)、啶嘧黄隆、吡氟禾草灵(丁酯)、fluazolate、flucarbazone、flufenacet、唑嘧磺草胺、氟烯草酸、丙炔氟草胺、flumipropyn、氟草隆、氟咯草隆、乙羧氟草醚(乙酯)、氟胺草唑、flupropacil、flupyrasulfuron(-methyl、sodium)、芴丁酸、氟啶草酮、氯氟吡氧乙酸、氟嘧醇、flurtamone、fluthiacet(-methyl)、fluthiamide、氟黄胺草醚、草铵磷(铵盐)、草甘磷(异丙铵盐)、halosafen、吡氟氯禾灵(乙氧基乙酯)、精吡氟氯禾灵(甲酯)、环嗪酮、咪草酯(甲酯)、imazamethapyr、imazamox、imazapic、灭草烟、灭草喹、咪草烟、咪唑黄隆、碘磺隆、碘苯腈、异丙乐灵、异丙隆、异噁隆、异噁酰草胺、isoxachlortole、isoxaflutole、噁草醚、乳氟禾草灵、环草定、利谷隆、2甲4氯、2甲4氯丙酸、苯噻草胺、苯嗪草酮、吡草胺、甲基苯噻隆、吡喃隆、秀谷隆、S-异丙甲草胺、磺草唑胺、甲氧隆、嗪草酮、甲黄隆(甲酯)、草达灭、绿谷隆、萘丙胺、萘氧丙草胺、草不隆、烟嘧黄隆、哒草伏、坪草丹、安磺乐灵、oxadiargyl、oxasulfuron、oxaziclomefone、噁草酮、乙氧氟草醚、百草枯、pelargonic acid、二甲戊乐灵、pentoxazone、甜菜宁、哌草磷、丙草胺、氟嘧黄隆(甲酯)、扑草净、毒草胺、敌稗、喔草酯、异丙草胺、戊炔草胺、苄草丹、氟磺隆、pyraflufen(-ethyl)、吡唑特、吡嘧黄隆(乙酯)、苄草唑、pyribenzoxim、稗草丹、哒草特、pyriminobac(-methyl)、嘧草硫醚、二氯喹啉酸、喹草酸、灭藻醌、喹禾灵(乙酯)、喹禾灵(四氢糠酯)、砜嘧黄隆、稀禾定、西玛津、西草净、sulcitrione、甲磺草胺、嘧黄隆(甲酯)、草锍磷、甲嘧磺隆、牧草胺、特丁噻草隆、tepraloxydim、特丁津、特丁净、噻吩草胺、噻呋酰胺、噻唑烟酸、thidiazimin、噻黄隆(甲酯)、杀草丹、仲草丹、肟草酮、野燕畏、醚苯黄隆、苯黄隆(甲酯)、绿草定、灭草环、氟乐灵和氟胺黄隆。
也可以是与其它已知活性化合物如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物养料和土壤结构改良剂一起的混合物。
活性化合物可以以其本身、以其制剂或由之经进一步稀释而制备的使用形式使用,如直接可用溶液、悬浮液、乳液、粉剂、膏剂和颗粒剂。它们以常规方法使用,例如浇泼、喷雾、弥雾或撒施等等。
本发明活性化合物可以在植物萌发前或后施用。它们也可以在播种前掺入土壤中。
所用的活性化合物的量可以在相当宽的范围内变化。用量基本上取决于所需的效果。通常,使用量在每公顷土表面积用1克至10千克之间,优选每公顷5克至5千克。
本发明活性化合物的制备和使用可以参见下列实施例。
制备实施例:
(方法(a))
将在50ml二甲基亚砜中的2.5g(10mmol)4-甲氧基-苯酚用1.6g氢化钠(纯度60%)处理。混合物在室温(大约20℃)下搅拌30分钟。之后加入3.2g(10mmol)4-(3,6-二氢-2,6-二氧代-4-三氟甲基-1(2H)-嘧啶-1-基)-2,5-二氟苯甲腈。反应混合物在60℃搅拌18小时,随后倒入大约等体积的1N盐酸中。获得的晶体产物通过抽吸过滤分离,与30ml乙酸乙酯和300ml乙醚的混合物一起搅拌,并抽吸过滤至干。有机母液在水泵真空下浓缩,残余物进行柱色谱(硅胶,氯仿/乙酸乙酯,体积比2∶1)。获得的第一级分在水泵真空下浓缩,残余物溶解于沸腾的二氯甲烷中;冷却后,滗析掉上清溶液剂,残余物用乙醚/异丙醚搅拌,晶体产物抽吸过滤分离。
由此获得0.90g(理论值的21%)4-(3,6-二氢-2,6-二氧代-4-三氟甲基-1(2H)嘧啶-1-基)-5-氟-2-(4-甲氧基-苯氧基)-苯甲腈,熔点84℃。
实施例2
(方法(b))
将0.50g(1.2mmol)4-(3,6-二氢-2,6-二氧代-4-三氟甲基-1(2H)-嘧啶-1-基)-5-氟-2-(4-甲氧基-苯氧基)-苯甲腈、0.20g(1.8mmol)硫酸二甲酯、0.30g(2.4mmol)碳酸钾和100ml丙酮的混合物回流15小时,随后在水泵真空下浓缩。残余物用50ml的1N盐酸/50ml乙酸乙酯震荡,分离出有机相,用硫酸钠干燥并过滤。滤液在水泵真空下浓缩,残余物溶解于乙酸乙酯中,溶液用5%磷酸氢二钠洗涤,用硫酸钠干燥并过滤。滤液用水泵真空浓缩,残余物用石油醚搅拌,溶剂在水泵真空下仔细蒸发掉。
由此给出0.3g(理论值的57%)4-(3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶-1-基)-5-氟-2-(4-甲氧基-苯氧基)-苯甲腈,熔点62℃。
实施例(Ⅵ-1)
将在100ml二氯甲烷和1.7g吡啶中的2.8g(11mmol)1-氨基-4-氰基-2-氟-5-(4-甲氧基-苯氧基)苯在室温(大约20℃)下用1.25g(12mmol)氯甲酸乙酯处理。混合物在室温下搅拌2小时,随后用1N盐酸震荡。有机相在水泵真空下浓缩,残余物用乙醚/异丙醚结晶,固体产物通过抽吸过滤分离。
由此给出1.2g(理论量的34%)N-(4-氰基-2-氟-5-(4-甲氧基-苯氧基)-苯基)-O-乙基-氨基甲酸酯。
1H-NMR(D6-DMSO,δ):7.85和7.89ppm。
式(Ⅸ)起始原料:
将在100ml N-甲基-吡咯烷酮中的1.3g(10mmol)4-甲氧基-苯酚在室温下用0.50g氢化钠(纯度60%)处理,在简短的搅拌之后,再用1.5g 4-氰基-2,5-二氟-苯胺处理。反应混合物在100℃下搅拌20小时。冷却后,混合物用水稀释,之后用1N盐酸稀释,并在搅拌2小时后,将固体产物抽滤过滤分离,并在陶土上干燥。
由此给出1.9g(理论值的73%)1-氨基-4-氰基-2-氟-5-(4-甲氧基-苯氧基)苯,熔点135℃。
类似于实施例(Ⅸ-1)可以制备出下列列于表2中的其它通式(Ⅸ)化合物。表2:式(Ⅸ)化合物的实例
实施例号 | Q | R4 | R5 | Xn | 物理数据 |
Ⅸ-10 | O | F | CN | (4-)F | |
Ⅸ-11 | O | F | CN | (3-)F | |
Ⅸ-12 | O | F | CN | (2-)F | |
Ⅸ-13 | O | F | CN | (4-)Br | |
Ⅸ-14 | O | H | CN | (4-)OH | |
Ⅸ-15 | O | H | CN | (4-)OCH3 | |
Ⅸ-16 | O | H | CN | (4-)Cl | |
Ⅸ-17 | O | H | CN | (4-)F | |
Ⅸ-18 | O | F | CF3 | - | |
Ⅸ-19 | O | F | CF3 | (4-)CH3 | |
Ⅸ-20 | O | F | CF3 | (4-)OCH3 | |
Ⅸ-21 | S | H | CN | - | |
Ⅸ-22 | S | F | CN | - | |
Ⅸ-23 | S | F | CN | (4-)Cl | |
Ⅸ-24 | S | F | CN | (4-)F | |
Ⅸ-25 | O | F | CF3 | (4-)CN |
应用实施例
实施例A
芽前试验
溶剂: 5份重量丙酮
乳化剂: 1份重量的烷基芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂混合,将所述量的乳化剂加入,并用水将此乳油稀释至所需浓度。
将试验植物的种子播入通常的土壤中,大约24小时后,土壤用活性化合物制剂浇水,在每单位面积上施用特定量的活性成分。选择喷雾液的浓度,使所需的活性化合物的特定量以1000升水/公顷的喷雾量施用。
三周后,将植物的损害程度与未处理对照的发育相比较,目测定出损害%。
数值的含义如下:
0%=无作用(与未处理相同)
100%=完全破坏
在此试验中,例如,制备实施例4和6的化合物对杂草显示出非常强的活性。
实施例B
芽后试验
溶剂: 5份重量丙酮
乳化剂: 1份重量的烷基芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂混合,将所述量的乳化剂加入,并用水将此乳油稀释至所需浓度。
向株高5-15厘米的试验植物按单位面积喷雾施用一定量的所需活性化合物制剂。选择喷雾液的浓度,使所需化合物的特定量以1,000升水/公顷的量施用。
三周后,将植物的损害程度与未处理对照相比较,定出损害%。
数值的含义如下:
0%=无作用(与未处理相同)
100%=完全破坏
在此试验中,例如制备实施例4和6的化合物对杂草显示出非常强的活性。
Claims (17)
1.通式(Ⅰ)的取代的苯基尿嘧啶,其中n 代表数字0、1、2、3、4或5,Q 代表O(氧)、S(硫)、SO、SO2、NH或N(烷基),R1 代表氢、氨基或任选被取代的烷基,R2 代表羧基、氰基、氨基甲酰基、硫代氨基甲酰基或代表各任选被
取代的烷基或烷氧基羰基,R3 代表氢、卤素或任选被取代的烷基,R4 代表氢、氰基、氨基甲酰基、硫代氨基甲酰基或卤素,R5 代表氰基、氨基甲酰基、硫代氨基甲酰基、卤素,或代表各任选
被取代的烷基或烷氧基,和X 代表羟基、巯基、氨基、硝基、氰基、羧基、氨基甲酰基、硫代
氨基甲酰基、卤素,或代表各任选被取代的烷基、烷氧基、烷硫
基、烷基亚磺酰基、烷基磺酰基、烷基氨基、二烷基氨基、烷基
羰基、烷氧基羰基、烷基氨基羰基、二烷基氨基羰基、烷基羰氧
基、烷氧基羰氧基、烷基氨基羰氧基、二烷基氨基羰氧基、苯基
羰氧基、烷基羰基氨基、烷氧基羰基氨基、烷基磺酰基氨基、链
烯基、链烯氧基、链烯氧基羰基、炔基、炔氧基或炔氧基羰基,
其中在n大于1的情况下,X在每一可能的化合物中也可以是不
同的上述基团。
2.根据权利要求1的取代的苯基尿嘧啶,其特征在于,n 代表数字0、1、2、3或4;Q 代表O(氧)、S(硫)、SO、SO2、NH或N(C1-C4-烷基),R1 代表氢、氨基或任选由氰基、羧基、氟、氯、C1-C4-烷氧基或C1-C4-
烷氧基羰基取代的C1-C4-烷基,R2 代表羧基、氰基、氨基甲酰基、硫代氨基甲酰基,或代表C1-C4-
烷基或C1-C4-烷氧基羰基,它们各任选由氰基、氟、氯或C1-C4-
烷氧基取代,R3 代表氢、氟、氯、溴,或代表任选由氟或氯取代的C1-C4-烷基,R4 代表氢、氰基、氨基甲酰基、硫代氨基甲酰基、氟、氯或溴,R5 代表氰基、氨基甲酰基、硫代氨基甲酰基、氟、氯、溴,或代表
C1-C4-烷基或C1-C4-烷氧基,它们各任选由氟和/或氯取代,和X 代表羟基、巯基、氨基、硝基、氰基、羧基、氨基甲酰基、硫代
氨基甲酰基、氟、氯、溴、碘,或代表烷基、烷氧基、烷硫基、
烷基亚磺酰基、烷基磺酰基或烷基氨基,它们各具有1至6个碳
原子且各任选由羟基、氰基、羧基、氨基甲酰基、氟、氯、C1-
C4-烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰
基、C1-C4-烷基羰基、C1-C4-烷氧基羰基、C2-C4-链烯氧基羰基、
C2-C4-炔氧基羰基、C1-C4-烷基氨基羰基、二(C1-C4-烷基)氨基-
羰基、苯氧基羰基、苄氧基羰基、苯基氨基羰基或苄基氨基羰基
取代,或代表在烷基基团中各具有1至6个碳原子的二烷基氨
基,或代表烷基羰基、烷氧基羰基、烷基氨基羰基、烷基羰氧基、
烷氧基羰氧基或烷基氨基羰氧基,它们在烷基基团中各具有1至
6个碳原子且它们各任选由氰基、氟、氯、溴或C1-C4-烷氧基取
代,或代表二烷基氨基羰基或二烷基氨基羰氧基,它们在烷基基
团中各具有1至6个碳原子,或代表苯基羰氧基,或代表烷基羰
基氨基、烷氧基羰基氨基、烷基磺酰基氨基,它们各任选由氟、
氯或溴取代,或代表链烯基、链烯氧基、链烯氧基羰基、炔基、
炔氧基或炔氧基羰基,它们各具有至多6个碳原子且它们各任选
由氰基、羧基、氟、氯、溴或C1-C4-烷氧基-羰基取代。
3.根据权利要求1的取代的苯基尿嘧啶,其特征在于,n 代表数字1、2或3;Q 代表O(氧)、S(硫)、SO、SO2、NH或N(甲基),R1 代表氢、氨基,或代表甲基、乙基、正或异丙基,它们各任选由
氰基、氟、氯、甲氧基或乙氧基取代,R2 代表羧基、氰基、氨基甲酰基、硫代氨基甲酰基,或代表甲基、
乙基、正或异丙基、甲氧基羰基、乙氧基羰基、正或异丙氧基羰
基,它们各任选由氰基、氟、氯、甲氧基或乙氧基取代,R3 代表氢、氟、氯、溴,或代表甲基或乙基,它们各任选由氟和/
或氯取代,R4 代表氢、氟或氯,R5 代表氰基、氨基甲酰基、硫代氨基甲酰基、氟、氯、溴、甲基或
三氟甲基;X 代表羟基、巯基、氨基、硝基、氰基、羧基、氨基甲酰基、硫代
氨基甲酰基、氟、氯、溴,或代表甲基、乙基、正或异丙基、正
-、异-、仲-或叔丁基、甲氧基、乙氧基、正或异丙氧基、正-、
异-、仲-或叔丁氧基、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、乙基磺酰基、甲基氨基、
乙基氨基、正或异丙基氨基、正-、异-、仲-或叔丁基氨基,它
们各任选由氰基、羧基、氨基甲酰基、氟、氯、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、乙基磺酰基、乙酰基、丙酰基、正
或异丁酰基、甲氧基羰基、乙氧基羰基、正或异丙氧羰基、烯丙
氧基羰基、1-丁烯-3-基氧基羰基、2-丁烯-4-基氧基羰基、炔丙
基氧基羰基、1-丁炔-3-基氧基羰基、2-丁炔-4-基氧基羰基、甲
基氨基羰基、乙基氨基羰基、正或异丙基氨基羰基、二甲基氨基
羰基、二乙基氨基羰基、苯氧基羰基、苄氧基羰基、苯基氨基羰
基或苄基氨基羰基取代,或代表二甲基氨基或二乙基氨基,或代
表乙酰基、丙酰基、正或异丁酰基、甲氧基羰基、乙氧基羰基、
正或异丙氧基羰基、甲基氨基羰基、乙基氨基羰基、正或异丙基
氨基羰基、乙酰氧基、丙酰氧基、正或异丁酰氧基、甲氧基羰氧
基、乙氧基羰氧基、正或异丙氧基羰氧基、甲基氨基羰氧基、乙
基氨基羰氧基、正或异丙基氨基羰氧基,它们各任选由氰基、氟、
氯、甲氧基、乙氧基、正或异丙氧基取代,或代表二甲基氨基羰
基、二乙基氨基羰基、二甲基氨基羰氧基或二乙基氨基羰氧基,
或代表苯基羰氧基,或代表乙酰基氨基、丙酰基氨基、正或异丁
酰基氨基、甲氧基羰基氨基、乙氧基羰基氨基、正或异丙氧基羰
基氨基、甲基磺酰基氨基、乙基磺酰基氨基、正或异丙基磺酰基
氨基、正-、异-、仲-或叔丁基磺酰基氨基,它们各任选由氟或
氯取代,或代表乙烯基、丙烯基、丙烯氧基、丙烯氧基羰基、乙
炔基、丙炔基、丙炔氧基或丙炔氧基羰基,它们各任选由氰基、
羧基、氟、氯、甲氧基羰基或乙氧基羰基取代。
4.根据权利要求1的取代的苯基尿嘧啶,其特征在于式(ⅠA)化合物其中R1 代表氢、氨基或甲基,R2 代表三氟甲基、一氯二氟甲基、二氟甲基或五氟乙基,R3 代表氢、氯或甲基,R4 代表氢、氟或氯,R5 代表氰基或硫代氨基甲酰基,和X 代表羟基、巯基、氨基、硝基、氰基、羧基、氨基甲酰基、硫代
氨基甲酰基、氟、氯、溴,或代表甲基、乙基、甲氧基、乙氧基、
甲硫基、乙硫基、甲氧基羰基或乙氧基羰基,它们各任选由氰基、
羧基、氨基甲酰基、氟、氯、甲氧基、乙氧基、正或异丙氧基、
甲氧基羰基、乙氧基羰基、正或异丙氧基羰基、烯丙氧基羰基、
炔丙氧基羰基、1-丁烯-3-基氧基羰基、2-丁烯-4-基氧基羰基、
炔丙氧基羰基、1-丁炔-3-基氧基羰基、2-丁炔-4-基氧基羰基、
甲基氨基羰基、乙基氨基羰基、正或异丙基氨基羰基、二甲基氨
基羰基、二乙基氨基羰基、苯氧基羰基、苄氧基羰基、苯基氨基
羰基或苄基氨基羰基取代,或代表由甲氧基羰基或乙氧基羰基取
代的乙烯基。
5.根据权利要求4的取代的苯基尿嘧啶,其特征在于,R1 代表甲基,R2 代表三氟甲基、一氯二氟甲基、二氟甲基或五氟乙基,R3 代表氢、氯或甲基,R4 代表氢、氟或氯,R5 代表氟、氯、溴或三氟甲基,和X 代表羟基、巯基、氨基、硝基、氰基、羧基、氨基甲酰基、硫代
氨基甲酰基、氟、氯、溴,或代表甲基、乙基、甲氧基、乙氧基、
甲硫基、乙硫基、甲氧基羰基或乙氧基羰基,它们各任选由氰基、
羧基、氨基甲酰基、氟、氯、甲氧基、乙氧基、正或异丙氧基、
甲氧基羰基、乙氧基羰基、正或异丙氧基羰基、烯丙氧基羰基、
炔丙氧基羰基、1-丁烯-3-基氧基羰基、2-丁烯-4-基氧基羰基、
炔丙氧基羰基、1-丁炔-3-基氧基羰基、2-丁炔-4-基氧基羰基、
甲基氨基羰基、乙基氨基羰基、正或异丙基氨基羰基、二甲基氨
基羰基、二乙基氨基羰基、苯氧基羰基、苄氧基羰基、苯基氨基
羰基或苄基氨基羰基取代,或代表由甲氧基羰基或乙氧基羰基取
代的乙烯基。
6.根据权利要求4的取代的苯基尿嘧啶,其特征在于,R1 代表氢、氨基或甲基,R2 代表羧基、氰基、氨基甲酰基、硫代氨基甲酰基、甲氧基羰基或
乙氧基羰基,R3 代表氢、氯或甲基,R4 代表氢、氟或氯,R5 代表氰基、硫代氨基甲酰基、氟、氯、溴或三氟甲基,和X 代表羟基、巯基、氨基、硝基、氰基、羧基、氨基甲酰基、硫代
氨基甲酰基、氟、氯、溴,或代表甲基、乙基、甲氧基、乙氧基、
甲硫基、乙硫基、甲氧基羰基或乙氧基羰基,它们各任选由氰基、
羧基、氨基甲酰基、氟、氯、甲氧基、乙氧基、正或异丙氧基、
甲氧基羰基、乙氧基羰基、正或异丙氧基羰基、烯丙氧基羰基、
炔丙氧基羰基、1-丁烯-3-基氧基羰基、2-丁烯-4-基氧基羰基、
炔丙氧基羰基、1-丁炔-3-基氧基羰基、2-丁炔-4-基氧基羰基、
甲基氨基羰基、乙基氨基羰基、正或异丙基氨基羰基、二甲基氨
基羰基、二乙基氨基羰基、苯氧基羰基、苄氧基羰基、苯基氨基
羰基或苄基氨基羰基取代,或代表由甲氧基羰基或乙氧基羰基取
代的乙烯基。
7.根据权利要求1至6之任一的取代的苯基尿嘧啶,其特征在于,n代表1。
8.根据权利要求1至7之任一的取代的苯基尿嘧啶,其特征在于,R2代表三氟甲基。
9.根据权利要求1至8之任一的取代的苯基尿嘧啶,其特征在于,R4代表氟。
10.根据权利要求1至9之任一的取代的苯基尿嘧啶,其特征在于,R5代表氰基或硫代氨基甲酰基。
11.制备权利要求1至10之任一的取代的苯基尿嘧啶的方法,其特征在于,(a)如果适合在反应辅助剂存在下和如果适合在稀释剂存在下,使通式(Ⅱ)的卤代苯基尿嘧啶
其中
R1、R2、R3、R4和R5具有权利要求1至10之任一中给出的含义,和
X1代表卤素与通式(Ⅲ)的芳基化合物其中n、Q和X具有权利要求1至10之任一中给出的含义,或通式(Ⅲ)化合物的金属盐反应或(b)如果适宜在反应辅助剂存在下和如果适宜在稀释剂存在下,使通式(Ⅳ)的氨基烯酸酯
其中
R2和R3具有权利要求1至10之任一中给出的含义,和
R 代表烷基、芳基或芳基烷基与通式(Ⅴ)的芳基异氰酸酯
其中
其中
n、Q、R4、R5和X具有权利要求1至10之任一中给出的含义,
其中
n、Q、R3、R4、R5和X具有权利要求1至10之任一中给出的含义和
其中
n、Q、R2、R3、R4、R5和X具有权利要求1至10之任一中给出的含义,与1-氨基氧基-2,4-二硝基-苯或通式(Ⅷ)的烷基化试剂反应
X2-A1 (Ⅷ)
其中
A1代表任选被取代的烷基和
X2代表卤素或基团-O-SO2-O-A1,且,如果适宜,随后用常规方式在取代基定义的范围内进行亲电或亲核和/或氧化或还原反应。
14.通式(Ⅸa)的苯胺衍生物其中n、R4和X具有权利要求1至7和9之任一中给出的含义,和Y 代表氰基、硫代氨基甲酰基或三氟甲基。
16.至少一种权利要求1至10之任一的取代的苯基尿嘧啶防治不希望的植物的应用。
17.除草组合物,其特征在于,它包含至少一种权利要求1至10之任一的取代的苯基尿嘧啶。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19830693 | 1998-07-09 | ||
DE19830693.8 | 1998-07-09 | ||
DE19853864A DE19853864A1 (de) | 1998-07-09 | 1998-11-23 | Substituierte Phenyluracile |
DE19853864.2 | 1998-11-23 |
Publications (1)
Publication Number | Publication Date |
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CN1314894A true CN1314894A (zh) | 2001-09-26 |
Family
ID=26047298
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN99810184.2A Pending CN1314894A (zh) | 1998-07-09 | 1999-07-02 | 取代的苯基尿嘧啶类化合物 |
Country Status (11)
Country | Link |
---|---|
US (2) | US6780821B1 (zh) |
EP (1) | EP1095027B1 (zh) |
JP (1) | JP2002520319A (zh) |
CN (1) | CN1314894A (zh) |
AT (1) | ATE297903T1 (zh) |
AU (1) | AU750045B2 (zh) |
BR (1) | BR9911978A (zh) |
CA (1) | CA2336762A1 (zh) |
PL (1) | PL345448A1 (zh) |
RU (1) | RU2001103888A (zh) |
WO (1) | WO2000002866A1 (zh) |
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IL139899A (en) | 1999-12-07 | 2005-06-19 | Sumitomo Chemical Co | Uracil compounds and use thereof |
DE19927612A1 (de) * | 1999-06-17 | 2000-12-21 | Bayer Ag | Substituierte Phenyluracile |
DE19954312A1 (de) * | 1999-11-11 | 2001-05-17 | Bayer Ag | Substituierte Phenyluracile |
JP4779199B2 (ja) * | 1999-12-07 | 2011-09-28 | 住友化学株式会社 | ウラシル化合物及びその用途 |
IL167957A (en) | 2000-02-04 | 2009-07-20 | Sumitomo Chemical Co | Hydroxypyridine compounds |
DE10016893A1 (de) | 2000-04-05 | 2001-10-18 | Bayer Ag | Substituierte Phenyluracile |
DE10051981A1 (de) | 2000-10-20 | 2002-05-02 | Bayer Ag | Substituierte Phenyluracile |
BR0117032A (pt) * | 2001-05-31 | 2004-04-20 | Sumitomo Chemical Co | Reguladores de crescimento de planta para coleta de algodão |
EP1736052B1 (en) * | 2001-05-31 | 2010-04-21 | Sumitomo Chemical Company, Limited | Stem/leaf desiccant |
JP2003104808A (ja) | 2001-09-28 | 2003-04-09 | Sumitomo Chem Co Ltd | 除草剤組成物 |
JP2003104810A (ja) | 2001-09-28 | 2003-04-09 | Sumitomo Chem Co Ltd | 除草剤組成物 |
JP2003104809A (ja) | 2001-09-28 | 2003-04-09 | Sumitomo Chem Co Ltd | 除草剤組成物 |
RU2372404C2 (ru) | 2001-10-19 | 2009-11-10 | Сумитомо Кемикал Компани, Лимитед | Метаболизирующий гербицид белок, его ген и их применение |
JP4779283B2 (ja) * | 2001-10-19 | 2011-09-28 | 住友化学株式会社 | 雑草防除剤代謝蛋白質、その遺伝子およびその利用 |
JP4092455B2 (ja) | 2001-11-29 | 2008-05-28 | 住友化学株式会社 | 除草剤組成物 |
JP2003160415A (ja) | 2001-11-29 | 2003-06-03 | Sumitomo Chem Co Ltd | 除草剤組成物 |
US20220411381A1 (en) | 2019-10-01 | 2022-12-29 | Bayer Aktiengesellschaft | Pyrimidinedione derivatives |
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US4388472A (en) * | 1979-07-18 | 1983-06-14 | Imperial Chemical Industries Plc | Substituted diphenyl ethers |
DK366887A (da) | 1986-07-31 | 1988-05-13 | Hoffmann La Roche | Pyrimidinderivater |
EP0260621A3 (de) | 1986-09-18 | 1989-03-15 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | 3-Aryluracil-enoläther und deren Verwendung zur Unkrautbekämpfung |
IL86462A (en) * | 1987-05-29 | 1992-12-01 | Fujisawa Pharmaceutical Co | Alkanesulfonanilide derivatives, processes for preparation thereof and pharmaceutical compositions comprising the same |
WO1991000278A1 (de) | 1989-06-29 | 1991-01-10 | Ciba-Geigy Ag | Heterocyclische verbindungen |
AU627906B2 (en) | 1989-07-14 | 1992-09-03 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
US5084084A (en) | 1989-07-14 | 1992-01-28 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
US5134144A (en) | 1989-11-20 | 1992-07-28 | Uniroyal Chemical Company, Inc. | Pesticidal 3-arylpyrimidinyl ethers and thioethers |
ATE111901T1 (de) | 1990-01-18 | 1994-10-15 | Nissan Chemical Ind Ltd | Uracilderivate und pestizide, die diese als wirksame stoffe enthalten. |
US4979982A (en) | 1990-02-02 | 1990-12-25 | Uniroyal Chemical Company, Inc. | Herbicidal cinnamic ester uracils |
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JP3089621B2 (ja) | 1990-12-17 | 2000-09-18 | 日産化学工業株式会社 | ウラシル誘導体 |
EP0517181B1 (en) | 1991-06-07 | 1995-09-20 | Sumitomo Chemical Company Limited | Amino uracil derivatives, and their production and use |
US5169430A (en) | 1991-08-09 | 1992-12-08 | Uniroyal Chemical Company, Inc. | Benzenesulfonamide derivatives and methods for their production |
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HUP9802196A3 (en) * | 1995-06-29 | 1999-03-01 | Bayer Agrochem Kk | Substituted cyanophenyl uracil derivatives, preparation and use thereof, insecticide and herbicide compositions containing these compounds as active ingredients |
DE19527570A1 (de) * | 1995-07-28 | 1997-01-30 | Bayer Ag | Substituierte Aminouracile |
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- 1999-07-02 AT AT99934556T patent/ATE297903T1/de not_active IP Right Cessation
- 1999-07-02 WO PCT/EP1999/004585 patent/WO2000002866A1/de active IP Right Grant
- 1999-07-02 CN CN99810184.2A patent/CN1314894A/zh active Pending
- 1999-07-02 EP EP99934556A patent/EP1095027B1/de not_active Expired - Lifetime
- 1999-07-02 RU RU2001103888/04A patent/RU2001103888A/ru not_active Application Discontinuation
- 1999-07-02 PL PL99345448A patent/PL345448A1/xx not_active Application Discontinuation
- 1999-07-02 CA CA002336762A patent/CA2336762A1/en not_active Abandoned
- 1999-07-02 JP JP2000559097A patent/JP2002520319A/ja active Pending
- 1999-07-02 US US09/720,892 patent/US6780821B1/en not_active Expired - Fee Related
- 1999-07-02 AU AU50299/99A patent/AU750045B2/en not_active Ceased
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Publication number | Publication date |
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ATE297903T1 (de) | 2005-07-15 |
JP2002520319A (ja) | 2002-07-09 |
WO2000002866A1 (de) | 2000-01-20 |
AU750045B2 (en) | 2002-07-11 |
US6780821B1 (en) | 2004-08-24 |
RU2001103888A (ru) | 2004-02-27 |
EP1095027A1 (de) | 2001-05-02 |
PL345448A1 (en) | 2001-12-17 |
CA2336762A1 (en) | 2000-01-20 |
AU5029999A (en) | 2000-02-01 |
US20040254206A1 (en) | 2004-12-16 |
BR9911978A (pt) | 2001-03-27 |
EP1095027B1 (de) | 2005-06-15 |
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