CN1196725A - 取代的氨基尿嘧啶 - Google Patents
取代的氨基尿嘧啶 Download PDFInfo
- Publication number
- CN1196725A CN1196725A CN96197016A CN96197016A CN1196725A CN 1196725 A CN1196725 A CN 1196725A CN 96197016 A CN96197016 A CN 96197016A CN 96197016 A CN96197016 A CN 96197016A CN 1196725 A CN1196725 A CN 1196725A
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- CN
- China
- Prior art keywords
- group
- alkyl
- represent
- substitution
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000004009 herbicide Substances 0.000 claims abstract description 8
- -1 Hydrogen Chemical class 0.000 claims description 119
- 150000001875 compounds Chemical class 0.000 claims description 56
- 239000000460 chlorine Substances 0.000 claims description 45
- 229910052801 chlorine Inorganic materials 0.000 claims description 44
- 229910052731 fluorine Inorganic materials 0.000 claims description 41
- 239000011737 fluorine Substances 0.000 claims description 41
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 34
- 238000006467 substitution reaction Methods 0.000 claims description 33
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 23
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 22
- 229910052794 bromium Inorganic materials 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 19
- BISHACNKZIBDFM-UHFFFAOYSA-N 5-amino-1h-pyrimidine-2,4-dione Chemical class NC1=CNC(=O)NC1=O BISHACNKZIBDFM-UHFFFAOYSA-N 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 11
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 230000002363 herbicidal effect Effects 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 150000002921 oxetanes Chemical class 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 230000002152 alkylating effect Effects 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000006003 dichloroethyl group Chemical group 0.000 claims description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 229910052751 metal Chemical group 0.000 claims description 3
- 239000002184 metal Chemical group 0.000 claims description 3
- 230000000269 nucleophilic effect Effects 0.000 claims description 3
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 3
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
- 229940035893 uracil Drugs 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 2
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 2
- 125000005981 pentynyl group Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 4
- 230000001473 noxious effect Effects 0.000 claims 3
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000002053 thietanyl group Chemical group 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 19
- 239000007858 starting material Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 239000002585 base Substances 0.000 description 10
- 244000025254 Cannabis sativa Species 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 240000001592 Amaranthus caudatus Species 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 241000790917 Dioxys <bee> Species 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 description 5
- 241001251949 Xanthium sibiricum Species 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 244000056139 Brassica cretica Species 0.000 description 4
- 235000003351 Brassica cretica Nutrition 0.000 description 4
- 235000003343 Brassica rupestris Nutrition 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical group CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- 235000010460 mustard Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 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
- 241000234653 Cyperus Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-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
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 239000004178 amaranth Substances 0.000 description 3
- 235000012735 amaranth Nutrition 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 125000003963 dichloro group Chemical group Cl* 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 244000304962 green bristle grass Species 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-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
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
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- 235000007320 Avena fatua Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 241001647031 Avena sterilis Species 0.000 description 2
- 235000004535 Avena sterilis Nutrition 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000005594 Phenmedipham Substances 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
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- VXMNDQDDWDDKOQ-UHFFFAOYSA-N Pyrazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C(O)=O)C)=N1 VXMNDQDDWDDKOQ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
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- 244000098338 Triticum aestivum Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004176 ammonification Methods 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 244000022185 broomcorn panic Species 0.000 description 2
- RIUXZHMCCFLRBI-UHFFFAOYSA-N chlorimuron Chemical compound COC1=CC(Cl)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 RIUXZHMCCFLRBI-UHFFFAOYSA-N 0.000 description 2
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
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- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 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
- 235000009566 rice Nutrition 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 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
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000003516 soil conditioner Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 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
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 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
- 150000003918 triazines Chemical class 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 group OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 125000006493 trifluoromethyl benzyl group Chemical group 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 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
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 150000003751 zinc Chemical class 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
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及通式(Ⅰ)的新的氨基尿嘧啶及其用作除草剂的用途,以及新的中间体,其中Q,R1,R2,R3,R4,R5,R6,和R7为说明书中的定义。
Description
本发明涉及新的取代的氨基尿嘧啶,其制备方法,用作除草剂的用途和新的中间体。
已知一些取代尿嘧啶具有除草活性(参考:EP 408 382/US5084084/US 5 127 935/US 5 154755,EP 563 384,EP 648 749,WO91/00278,US 4979982,US 5169430)。可是,到目前为止,上述化合物都不具有值得一提的重要性。
相应的,本发明提供了通式(I)的新的取代氨基尿嘧啶:
其中
Q代表O,S,SO或SO2,
R1代表氢,氰基或卤素,
R2代表氰基或硫代氨基甲酰基,
R3代表氢或代表分别可选择取代的烷基,链烯基,链炔基,环烷基,环烷基烷基,芳基,芳烷基,杂环基或杂环基烷基,
R4代表氢,卤素或代表分别可选择取代的烷基或烷氧基,
R5代表可选择取代的烷基,
R6代表氢或代表分别可选择取代的烷基,链烯基或链炔基,和
R7代表氢或代表分别可选择取代的烷基,链烯基或链炔基。
通式(I)的新的氨基尿嘧啶是通过
(a)通式(II)的取代尿嘧啶与亲电子的胺化剂,如果适合,在反应助剂存在下,和如果适合,在稀释剂存在下反应而制备,
其中
Q,R1,R2,R3,R4和R5各自为上述定义
或
(b)通式(Ia)的氨基尿嘧啶与硫化氢,如果适合,在反应助剂存在下,和如果适合,在稀释剂存在下反应而制备,
其中
Q,R1,R3,R4,R5,R6和R7各自为上述定义
或
其中
Q,R1,R2,R3,R4和R5各自为上述定义,
X-R7(IIIa) X-R8(IIIb)
其中
R7,和R8各自为上述定义和
X代表卤素或基团-O-SO2-O-R7或-O-SO2-O-R8,
或
其中R1,R2,R4,R5,R6,R7各自为上述定义
X代表卤素,
M-Q-R3(V)
其中
Q和R3各自为上述定义和
M代表氢或金属等价物。
通式(I)的新的取代氨基尿嘧啶具有强的除草性质。
在定义中,饱和或不饱和烃链,如烷基,链烯基或链炔基各自为直链或支链的。
卤素通常代表氟,氯,溴或碘,优选氟,氯或溴,特别是氟或氯。
本发明优选提供了式(I)化合物,其中
Q代表O,S,SO或SO2,
R1代表氢,氰基,氟或氯,
R2代表氰基或硫代氨基甲酰基,
R3代表氢,代表各自可被氰基,羧基,氟,氯,溴或被C1-C4-烷氧基,C1-C4-烷基-羰基,C1-C4-烷氧基羰基或N-(C1-C4-烷基)-N-苯基-氨基羰基(各自可被氟和/或氯可选择取代)可选择取代的各自至多10碳原子的烷基,链烯基或链炔基,
R3还代表烷基部分具有3至8碳原子的环烷基或环烷基烷基,且烷基部分可选择的至多4碳原子,每个基团可选择的被氰基,羧基,氟,氯,溴,C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷基-羰基或C1-C4-烷氧基-羰基取代,
R3还代表芳基部分具有6至10碳原子的芳基或芳烷基,且烷基部分可选择的至多4碳原子,每个基团可选择的被氰基,羧基,硝基,氨基甲酰基,硫代氨基甲酰基,氟,氯,溴,被C1-C4-烷基,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-羰基或C1-C4-烷氧基-羰基(各自可被氟和/或氯可选择取代),被苯基,苯氧基或苯硫基(各自可被氟,氯,溴,氰基,甲基,甲氧基,三氟甲基和/或三氟甲氧基可选择取代)取代,或
R3还代表呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,氧杂环丁烷,硫杂环丁烷(thielanyl),噁唑基,异噁唑基,噻唑基,噁二唑基,噻二唑基,吡唑基,吡啶基,嘧啶基,三嗪基,吲哚基,喹啉基或喹喔啉基,上述基团各自可选择的被氰基,羧基,氨基甲酰基,硫代氨基甲酰基,氟,氯,溴,被C1-C4-烷基,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-羰基或C1-C4-烷氧基-羰基(各自可被氟和/或氯可选择取代),被苯基,苯氧基或苯硫基(各自可被氟,氯,溴,氰基,甲基,甲氧基,三氟甲基和/或三氟甲氧基可选择取代)取代,
R4代表氢,氟,氯,溴或代表分别可选择氟-和/或氯-取代的、各自具有1至4碳原子的烷基或烷氧基,
R5代表可选择氟-和/或氯-取代的、具有1至4碳原子的烷基,
R6代表氢或代表分别可选择氟-,氯-或C1-C4-烷氧基-取代的、各自至多具有6碳原子的烷基,链烯基或链炔基,和
R7代表氢或代表分别可选择氟-,氯-或C1-C4-烷氧基-取代的、各自至多具有6碳原子的烷基,链烯基或链炔基。
本发明特别提供式(I)化合物其中:
Q代表O,S,SO或SO2,
R1代表氢,氟或氯,
R2代表氰基或硫代氨基甲酰基,
R3代表氢,代表分别可选择氰基-,羧基-,氟-,氯-,甲氧基-,乙氧基-,正-或异-丙氧基,乙酰基-,丙酰基-,甲氧基羰基-,乙氧基羰基-,正-或异-丙氧基羰基-取代的甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基-,正-,异-,仲-或叔-戊基,丙烯基,丁烯基,戊烯基,丙炔基,丁炔基或戊炔基,代表分别可选择氰基-,羧基-,氟-,氯-,溴-,甲基-,乙基-,正-或异-丙基,甲氧基-,乙氧基-,正-或异-丙氧基-,乙酰基-或丙酰基-,甲氧基羰基-,乙氧基羰基-,正-或异-丙氧基羰基-取代的环丙基,环丁基,环戊基,环己基,环丙基甲基,环丁基甲基,环戊基甲基或环己基甲基,代表分别可选择氰基-,羧基-,硝基-,氨基甲酰基-,硫代氨基甲酰基-,氟-,氯-,溴-,甲基-,乙基-,正-或异-丙基,正-,异-,仲-或叔-丁基-,三氟甲基-,甲氧基-,乙氧基-,正-或异-丙氧基-,甲硫基-,乙硫基-,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-,甲氧基羰基-,乙氧基羰基-,正-或异-丙氧基羰基-取代的苯基,苄基或苯乙基,或代表分别可选择氰基-,羧基-,氨基甲酰基-,硫代氨基甲酰基-,氟-,氯-,溴-,甲基-,乙基-,正-或异-丙基-,甲氧基-,乙氧基-,正-或异-丙氧基-,甲硫基-,乙硫基-,甲基亚磺酰基-,乙基亚磺酰基-,甲基磺酰基,乙基磺酰基,乙酰基-,丙酰基-,甲氧基羰基-,乙氧基羰基-,正-或异-丙氧基羰基-,苯基-,苯氧基-或苯硫基-取代的呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,氧杂环丁烷,硫杂环丁烷,噁唑基,异噁唑基,噻唑基,噁二唑基,噻二唑基,吡唑基,吡啶基,嘧啶基,三嗪基,吲哚基,喹啉基或喹喔啉基,
R4代表氢,氟,氯,溴或甲基,
R5代表甲基,乙基,二氟甲基,二氯甲基,三氟甲基,三氯甲基,氯二氟甲基,氟二氯甲基,氯乙基,氟乙基,二氯乙基,二氟乙基,氯氟乙基,氯二氟乙基,氟二氯乙基,三氟乙基,四氟乙基,氯三氟乙基或五氟乙基,
R6代表氢或代表分别可选择氟-,氯-,甲氧基-,或乙氧基-取代的甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,丙烯基,丁烯基,丙炔基或丁炔基,和
R7代表氢或代表分别可选择氟-,氯-,甲氧基-,或乙氧基-取代的甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,丙烯基,丁烯基,丙炔基或丁炔基。
上述列示的通式或优选范围的基团定义,不仅适用于式(I)的终产物,而且相应的适用于各种情况下制备所需的起始物和/或中间体。上述基团的定义可根据需要彼此组合,因此包括所示优选范围间的组合。
根据本发明的式(I)化合物的实例列示如下。
第1组
R3具有以下列示的含义:
氢,甲基,乙基,正-或异-苯基,正-,异-,仲-或叔-丁基,正-,异-,仲-或叔-戊基,二氟甲基,三氟甲基,氯二氟甲基,氟二氯甲基,氟乙基,氯乙基,氯氟乙基,二氟乙基,二氯乙基,三氟乙基,三氯乙基,氯二氟乙基,四氟乙基,氯三氟乙基,五氟乙基,氟丙基,氯丙基,二氟丙基,二氯丙基,三氟丙基,三氯丙基,氰基甲基,氰基乙基,氰基丙基,氰基丁基,羧基甲基,羧基乙基,羧基丙基,羧基丁基,甲氧基甲基,乙氧基甲基,丙氧基甲基,甲氧基乙基,乙氧基乙基,丙氧基乙基,甲氧基丙基,乙氧基丙基,丙氧基丙基,甲氧基羰基甲基,乙氧基羰基甲基,丙氧基羰基甲基,甲氧基羰基乙基,乙氧基羰基乙基,丙氧基羰基乙基,甲氧基羰基丙基,乙氧基羰基丙基,丙氧基羰基丙基,1-丙烯-3-基(烯丙基),3-甲基-1-丙烯-3-基,2-丁烯-4-基(巴豆基),1-丙炔-3-基(炔丙基),3-甲基-1-丙炔-3-基,2-丁炔-4-基,环丙基,氰基环丙基,羧基环丙基,二氟环丙基,二氯环丙基,甲基环丙基,甲氧基羰基环丙基,乙氧基羰基环丙基,环丁基,氰基环丁基,羧基环丁基,二氟环丁基,三氟环丁基,四氟环丁基,氯三氟环丁基,甲基环丁基,环戊基,氰基环戊基,羧基环戊基,氟环戊基,氯环戊基,二氟环戊基,二氯环戊基,甲基环戊基,甲氧基羰基环戊基,乙氧基羰基环戊基,环己基,氰基环己基,羧基环己基,氟环己基,氯环己基,二氟环己基,二氯环己基,甲基环己基,三氟甲基环己基,甲氧基羰基环己基,乙氧基羰基环己基,环丙基甲基,二氟环丙基甲基,二氯环丙基甲基,环丁基甲基,环戊基甲基,环己基甲基,氰基环己基甲基,羧基环己基甲基,氟环己基甲基,氯环己基甲基,甲基环己基甲基,三氟甲基环己基甲基,苯基,氰基苯基,羧基苯基,硝基苯基,氟苯基,氯苯基,溴苯基,甲基苯基,三氟甲基苯基,甲氧基苯基,二氟甲氧基苯基,三氟甲氧基苯基,甲氧基羰基苯基,乙氧基羰基苯基,苄基,氰基苄基,羧基苄基,氟苄基,氯苄基,甲基苄基,三氟甲基苄基,甲氧基苄基,二氟甲氧基苄基,三氟甲氧基苄基,甲氧基羰基苄基,乙氧基羰基苄基,苯基乙基,呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,氧杂环丁烷,噁唑基,异噁唑基。
第2组
R3为上述第1组中给出的定义。
R3为上述第1组中给出的定义。第4组R3为上述第1组中给出的定义。第5组R3为上述第1组中给出的定义。第6组R3为上述第1组中给出的定义。第7组R3为上述第1组中给出的定义。第8组R3为上述第1组中给出的定义。第9组R3为上述第1组中给出的定义。第10组R3为上述第1组中给出的定义。第11组R3为上述第1组中给出的定义。第12组R3为上述第1组中给出的定义。第13组R3为上述第1组中给出的定义。第14组R3为上述第1组中给出的定义。第15组R3为上述第1组中给出的定义。第16组R3为上述第1组中给出的定义。第17组R3为上述第1组中给出的定义。第18组R3为上述第1组中给出的定义。第19组
R3为上述第1组中给出的定义。
第20组
R3为上述第1组中给出的定义。
例如,应用1-(2-氯-4-氰基-5-氰基甲氧基-苯基)-3,6-二氢-2,6-二氧-4-二氟甲基-1(2H)-嘧啶作为起始物和1-氨基氧-2,4-二硝基苯作为亲电子胺化剂,本发明方法(a)中的反应过程可用下式列示:
例如,应用1-(4-氰基-5-二氟甲氧基-苯基)-3,6-二氢-2,6-二氧-3-氨基-4-氯二氟甲基-1(2H)-嘧啶作为起始物,本发明方法(b)中的反应过程可用下式列示:
例如,应用1-(4-氰基-2,5-二氟-苯基)-3,6-二氢-2,6-二氧-5-氯-4-三氟甲基-1(2H)-嘧啶和甲醇钠作为起始物,本发明方法(d)中的反应过程可用下式列示:
式(II)提供了在根据本发明制备式(I)化合物的方法(a)中用作起始物的取代尿嘧啶的总的定义。在式(II)中,Q,R1,R2,R3,R4,和R5各自优选或特别优选的定义已经在上述制备根据本发明的式(I)化合物的有关描述中作过说明,为其中优选或特别优选的Q,R1,R2,R3,R4,和R5。
式(II)的起始物是已知的和/或可通过已知方法制备的(参考:EP 408382,制备实施例)。
在进行根据本发明的方法(a)中使用了亲电子胺化剂。适合的胺化剂是常规的亲电子胺化剂。例如包括1-氨基氧-2,4-二硝基-苯(2,4-二硝基-苯基-羟基胺)和羟基胺-O-磺酸。
式(Ia)提供了在根据本发明制备式(I)化合物的方法(b)中用作起始物的氨基尿嘧啶的总的定义。在式(Ia)中,Q,R1,R3,R4,R5,R6和R7各自优选或特别优选的定义,已经在上述制备根据本发明的式(I)化合物的有关描述中作过说明,为其中优选或特别优选的Q,R1,R3,R4,R5,R6和R7。
根据本发明,式(Ia)的起始物是新的化合物;它们可通过根据本发明的方法(a)或(c)制备。
式(Ib)提供了在根据本发明制备式(I)化合物的方法(c)中用作起始物的氨基尿嘧啶的总的定义。在式(Ib)中,Q,R1,R2,R3,R4,和R5各自优选或特别优选的定义,已经在上述制备根据本发明的式(I)化合物的有关描述中作过说明,为其中优选或特别优选的Q,R1,R2,R3,R4,和R5。
根据本发明,式(Ib)的起始物是新的化合物;它们可通过根据本发明的方法(a)或(b)制备。
式(IIIa)和(IIIb)提供了在根据本发明制备式(I)化合物的方法(c)中也用作起始物的烷基化试剂的总的定义。在式(IIIa)和(IIIb)中,R7和R8各自优选或特别优选的定义,已经在上述制备根据本发明的式(I)化合物的有关描述中作过说明,为其中优选或特别优选的R7和R8;X优选代表氟,氯,溴或碘,特别是氯,溴或碘。
式(IV)提供了在根据本发明制备式(I)化合物的方法(d)中用作起始物的氨基尿嘧啶的总的定义。在式(IV)中,R1,R2,R4,R5,R6和R7,各自优选或特别优选的定义已经在上述制备根据本发明的式(I)化合物的描述中已作说明,为其中优选或特别优选的Q,R1,R2,R4,R5R6和R7;X优选代表氟,氯或溴,特别是氯或溴。
式(IV)的起始物是已知的和/或可通过已知方法制备的(参考:EP 648749)。
式(V)提供了在根据本发明制备式(I)化合物的方法(d)中也用作起始物的亲核化合物的总的定义。在式(V)中,Q和R3各自优选或特别优选的定义已经在上述制备根据本发明的式(I)化合物的有关描述中作过说明,为其中优选或特别优选的Q和R3;M优选的代表锂,钠,钾。
式(V)的起始物是已知的用于合成的化合物。
根据本发明制备式(I)化合物的方法(a),(b),(c)和(d)优选在适合的反应助剂存在下进行。适合的反应助剂通常是常规的无机或有机碱或酸接受体。它们优选的包括碱金属或碱土金属乙酸盐,氨化物,碳酸盐,碳酸氢盐,氢化物,氢氧化物或醇化物,例如乙酸钠,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,甲醇钠或甲醇钾,乙醇钠或乙醇钾,正-或异-丙醇钠或正-或异-丙醇钾,正-,异-,仲或叔-丁醇钠,正-,异-,仲或叔-丁醇钾;以及有机氮化合物的碱,例如,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-苄胺,吡啶,2-甲基-,3-甲基-,4-甲基、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),和1,8-二氮杂二环[5,4,0]-十一-7-烯(DBU)。
根据本发明制备式(I)化合物的方法(a),(b),(c)和(d)优选在稀释剂存在下进行。适合的稀释剂通常是常规的有机溶剂。它们优选的包括可选择卤代的脂肪族,环脂族和芳香烃,如戊烷、己烷、庚烷、石油醚、石脑油、汽油、苯、甲苯、二甲苯、氯苯、二氯苯、环己烷、甲基环己烷、二氯甲烷、三氯甲烷(氯仿)或四氯化碳,二烷基醚类如乙醚、二异丙基醚、甲基叔丁基醚(MTBE)、乙基叔丁基醚、甲基叔戊基醚(TAME)、乙基叔戊基醚、四氢呋喃(THF)、1,4-二噁烷、乙二醇二甲基醚或和乙二醇二乙基醚、二乙二醇二甲基醚或二乙二醇二乙基醚;二烷基酮类如丙酮、丁酮(甲基乙基酮)、甲基异丙基酮或甲基异丁基酮,腈类如乙腈、丙腈、丁腈或苄腈,酰胺类如N,N-二甲基甲酰胺(DMF)、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、乙酸乙酯,乙酸正丙酯或乙酸异丙酯、乙酸正-、异-或仲-丁基酯;亚砜类如二甲基亚砜;醇类如甲醇、乙醇、正-或异-丙醇,正-、异-、仲-或叔-丁醇、乙二醇单甲基醚或乙二醇单乙基醚、二乙二醇单甲基醚或二乙二醇单乙基醚;及其与水或纯水的混合物。
在根据本发明的方法(a),(b),(c)和(d)中的反应温度可在相当宽的范围内变化。反应通常在-20℃至+150℃,优选0℃至120℃的温度下进行。
根据本发明的方法(a),(b),(c)和(d)通常在大气压力下进行。可是也可在提高或降低的压力下进行-通常的压力是0.1巴-10巴。
为了进行根据本发明的方法(a),(b),(c)和(d),通常使用大约等摩尔量的起始物。可是,也可以使其中的一种成分过量。通常,反应在反应助剂存在下在适合的稀释剂中进行,并在所需的反应温度下搅拌反应混合物数小时。采用常规的方法进行加工处理(参考制备实施例)。
根据本发明的化合物可用作脱叶剂,干燥剂,除草秆剂,特别是除草剂。从广义上讲,杂草应理解为生长在不适合场所的所有植物。根据本发明的物质是否用作灭生性或选择性除草剂基本上是根据其使用量而确定。
根据本发明的活性化合物例如可用于下述相关的植物:
双子叶杂草属:白芥,独行菜,猪殃殃,繁缕,母菊,春黄菊,辣子草,藜,荨麻,千里光,苋,马齿苋,苍耳,旋花,牵牛,蓼,田菁,豚草,蓟,飞廉,苦苣菜,龙葵,蔊菜,水叶松,母草,野芝麻,婆婆纳,茼麻,刺果,曼陀罗,堇菜,鼬瓣花,罂粟,矢车菊,车轴草,毛茛和蒲公英。
双子叶作物属:棉,大豆,甜菜,胡萝卜,菜豆,豌豆,茄,亚麻,甘薯,巢菜,烟草,番茄,花生,甘蓝,莴苣,黄瓜和葫芦。
单子叶杂草属:稗,狗尾草,黍,马唐,梯牧草,早熟禾,羊茅,牛筋草,臂形草,黑麦草,雀麦,燕麦,莎草,蜀黍,冰草,洋狗尾草,鸭舌草,飘拂草,慈菇,针蔺,_草,雀稗,Ischaemum,尖瓣花,龙爪茅,剪股颍,看麦娘和风草。
单子叶作物属:水稻,玉米,小麦,大麦,燕麦,黑麦,高粱,黍,甘蔗,凤梨,石刁柏和葱。
可是,根据本发明活性化合物的应用不限制在上述属中,对其它植物它们也以同样方式具有相同的作用。
根据其浓度,式(I)化合物适合于灭生性地防治杂草,例如在工业区和铁轨,种树或没种树的路或广场。同样,根据本发明的式(I)化合物还可用来防治多年生栽培作物中的杂草,并可选择性地在一年生栽培作物中防治杂草,多年生栽培作物例如为森林,观赏树木,果园,葡萄园,柑桔园,坚果园,香蕉园,咖啡园,茶园,橡胶园,油棕园,可可园,种植的小果和啤酒花,草皮,草地和牧草。
根据本发明的式(I)活性化合物特别适合于在单子叶和双子叶作物中,在苗前或苗后选择性地防治单子叶和双子叶杂草。
本活性化合物可被转化成为常规的制剂,如溶液剂,乳剂,可湿性粉剂,悬浮剂,粉剂,细粉剂,糊剂,可溶粉剂,颗粒剂,浓悬浮乳剂,用活性化合物浸渍的天然和合成材料,和在聚合物中的微细胶囊。
这些制剂是以已知方法生产的,例如,通过将活性成分与填充剂,即液体溶剂和/或固体载体混合而生产,制剂中可选择的可使用表面活性剂,即乳化剂和/或分散剂,和/或成泡剂。
在使用水作为填充剂的情况下,例如,也可使用有机溶剂作为助溶剂。适当的液体溶剂主要有:芳香烃类,如二甲苯,甲苯或烷基萘,氯代芳烃类或氯代脂肪烃类,如氯苯,二氯乙烷或二氯甲烷,脂肪烃类,如环己烷或烷属烃,例如矿物油馏份,矿物油和植物油,醇类,如丁醇或乙二醇及其醚和酯类,酮类,如丙酮,甲基乙基酮,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。
适当的固体载体有:
例如,铵盐和天然矿物粉末,如高岭土,粘土,滑石,白垩,石英,硅镁土,蒙脱土或硅藻土,和合成矿物粉末,如高分散二氧化硅,氧化铝和硅酸盐;适合颗粒剂的固体载体有:例如,粉碎和分级的天然岩石,如方解石,大理石,浮石,海泡石和白云石,以及无机的合成颗粒和有机粉末,和有机材料的颗粒如锯末,坚果壳,玉米穗茎和烟草茎;适当的乳化剂和/或成泡剂有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯,聚氧乙烯脂肪醇醚,例如烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白水解产物;适合的分散剂有:例如木质素亚磺酸废液和甲基纤维素。
在制剂中还可使用粘着剂如羧甲基纤维素和粉末、颗粒或胶乳状天然和合成聚合物,如阿拉伯树胶,聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂如脑磷脂和卵磷脂,和合成磷脂。其它的粘着剂可以是矿物油和植物油。
可能使用着色剂如无机颜料,例如氧化铁,氧化钛和普鲁士兰,和有机染料,如茜素染料,偶氮染料和金属酞菁染料,和痕量营养物如金属盐,例如,铁、锰、硼、钴、铜、钼和锌盐。
制剂中通常含有按重量计0.1%至95%,优选按重量计0.5%至90%的活性化合物。
在防治杂草时,根据本发明的活性化合物可以其自身或与已知除草剂的混合物制剂形式使用,在这种情况下,可能的制剂是即用制剂或桶混合物形式。
上述混合物的适合的混合成分是已知除草剂,例如N-酰苯胺,如吡氟草胺和敌稗;芳基羧酸,如二氯吡啶甲酸,麦草畏,毒莠定;芳氧基烷醇酸,如2,4-滴,2,4-滴丁酸,2,4-滴丙酸,氟草定,2甲4氯,2甲4氯丙酸和绿草定;芳氧基-苯氧基-烷醇酸酯,如禾草灵,噁唑禾草灵,精吡氟禾草灵,盖草能和喹禾灵;丫嗪酮如杀草敏和达草灭;氨基甲酸酯如氯苯胺灵,乙苯敌草,甜菜宁和苯胺灵;氯乙酰苯胺,如甲草胺,乙草胺,丁草胺,吡草胺,乙基乙草胺,丙草胺和扑草胺;二硝基苯胺,如胺黄灵,胺硝草和氟乐灵;二苯基醚如氟锁草醚,甲羧除草醚,乙羧除草醚,氟磺胺草醚,halosafen,克阔乐和氟硝草醚;脲类,如氯麦隆,敌草隆,伏草隆,异丙隆,利谷隆和甲基苯噻隆;羟胺类,如枯杀达,烯草酮,噻草酮,稀禾定和肟草酮;咪唑啉酮,如灭草烟,咪草酯,灭草烟和灭草喹;腈类,如溴苯腈,敌草腈和碘苯腈;氧乙酰胺,如苯噻草胺;磺酰脲类,如amidosulfuron,吡嘧磺隆,氯嘧黄隆,氯黄隆,醚磺隆,甲磺隆,烟嘧黄隆,氯嘧黄隆,吡嘧磺隆,噻苯隆,醚苯黄隆和苯磺隆;硫代氨基甲酸酯,如苏达灭,草灭特,燕麦敌,扑草灭,禾草畏,草达灭,苄草丹,杀草丹和野麦畏;三嗪类,如阿特拉津,草净津,西玛津,西草净,去草净和特丁津;三嗪酮,如六嗪同,苯嗪草和嗪草酮;和其它类,如氨基三唑,呋草黄,噻草平,噁庚草烷,广灭宁,二氯吡啶酸,燕麦枯,氟硫草定,唑草定,氟略草酮,草铵膦,草甘膦,异噁草胺,达草止,快杀稗,喹草酸,草硫膦和灭草环。
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,植物营养剂和土壤结构改良剂的混合物也是可能的。
本活性化合物可以其本身或其制剂形式,或从中进一步稀释制备的应用形式使用,如现用溶液,悬浮液,乳液,粉剂,糊剂或颗粒剂。可以常规方式使用活性化合物,例如泼浇,喷雾,弥雾或分散。
可在植物苗前或苗后使用根据本发明的活性化合物。还可在播种前将活性化合物混入土壤中。
使用的活性化合物的量可在相当宽的范围内变化。这要根据所需效果而确定。通常,用量为对每公顷表土使用1g至10kg活性化合物,优选5g至5kg活性化合物。
根据本发明活性化合物的制备和应用可参见下述实施例。
制备实施例:
(方法(a))
将2.0g(6mmol)的1-(4-氰基-2-氟-5-甲氧基-苯基)-3,6-二氢-2,6-二氧-4-三氟甲基-1(2H)-嘧啶,0.5g(6mmol)的碳酸氢钠和10ml的二甲基甲酰胺的混合物在20℃下搅拌1小时。然后加入0.6g(3mmol)的1-氨基氧-2,4-二硝基-苯并在20℃下搅拌反应混合物24小时。再加入0.3g(1.5mmol)的1-氨基氧-2,4-二硝基-苯后,搅拌混合物3天;再加入0.3g(1.5mmol)的1-氨基氧-2,4-二硝基-苯,再连续搅拌3天。然后将50ml乙酸乙酯和50ml饱和氯化钠水溶液加入混合物中。振荡混合物,分离掉有机相,水相用乙酸乙酯提取三次。将合并的有机溶液用水冲洗两次,用硫酸钠干燥,用5cm的硅胶干燥,并用300ml的乙酸乙酯冲洗。然后用真空水泵浓缩混合物,剩余物用乙酸乙酯研制,过滤分离结晶产物。
得到1.1g(理论值的53%)的1-(4-氰基-2-氟-5-甲氧基-苯基)-3,6-二氢-2,6-二氧-3-氨基-4-三氟甲基-1(2H)-嘧啶,熔点241℃。
通过实施例1的方法,并根据本发明制备方法的一般描述,例如还可制备列示于下述表1的式(I)化合物。表1:式(I)化合物的实例实施 Q R1 R2 R3 R4 R5 R6 R7 熔点例号 (℃)2 O H CN CH3 H CF3 H H3 O F CSNH2 CH3 H CF3 H H4 O F CN C2H5 H CF3 H H 685 O F CSNH2 C2H5 H CF3 H H6 O F CN
H CF3 H H (非晶形)7 O F CN
H CF3 H H (非晶形)8 O F CN
H CF3 H H实施 Q R1 R2 R3 R4 R5 R6 R7 熔点例号 (℃)9 S F CN CH3 H CF3 H H10 S F CN CH2C6H5 H CF3 H H11 O F CN CH2C6H5 H CF3 H H 6212 O F CSNH2 CH2C6H5 H CF3 H H13 O F CN H H CF3 H H14 O F CN
H CF3 H H15 O F CN
H CF3 H H16 O F CN
CH3 CF3 H H17 O F CN
CH3 CF3 H H18 O F CN
CH3 CF3 H H19 O F CN CH3 H CF3 CH3 CH320 O F CN CH3 H CF3 H CH321 O F CN CH3 H CHF2 H H实施 Q R1 R2 R3 R4 R5 R6R7 熔点例号 (℃)22 O F CN CH3 H CFCl2 H H23 O H CN
H CF3 H H24 O H CN
H CF3 H H25 S H CN
Cl CF3 H CH326 O F CN C3H7-i H CF3 H H27 O F CSNH2 C3H7-i H CF3 H H28 S F CN C3H7-n H CF3 H H29 S F CSNH2 C3H7-n H CF3 H H30 S F CN H H CF3 H H31 O F CSNH2 H H CF3 H H32 S F CSNH2 H H CF3 H H实施 Q R1 R2 R3 R4 R5 R6 R7 熔点例号 (℃)33 O F CN
H CF3 H H 18634 O F CN
H CF3 H H35 O F CN
H CF3 H H 22736 O F CN
H CF3 H H 196式(II)的起始物:
实施例(II-1)
将3.8g(12mmol)的1-(4-氰基-2,5-二氟-苯基)-3,6-二氢-2,6-二氧-4-三氟甲基-1(2H)-嘧啶,1.5g(21mmol)的甲醇钠和50ml的N-甲基-吡咯烷酮的混合物在130℃下搅拌36小时。冷却混合物,用乙酸乙酯稀释至其大约三倍体积并用水冲洗,通过硅胶柱色谱(己烷/乙酸乙酯1/1(v/v))分离产物。
得到1.6g(理论值的41%)的1-(4-氰基-2-氟-5-甲氧基-苯基)-3,6-二氢-2,6-二氧-4-三氟甲基-1(2H)-嘧啶,熔点114℃。
药效实施例:
实施例A
苗前试验
溶剂: 5重量份丙酮
乳化剂: 1重量份烷基芳基聚乙二醇醚
为了制备活性化合物的适合制剂,将1重量份的活性化合物与预定量的溶剂混合,加入预定量的乳化剂并用水稀释浓缩物得到所需浓度的处理液。
将供试植物的种子播种到正常的土壤中,大约24小时后,用活性化合物的制剂灌溉。较好的是使每单位面积的浇水量保持一致。在制备物中,活性化合物的浓度并不重要,只有每单位面积的活性化合物的施用量是重要的。
三周后,与未处理对照物的发育比较,评价对植物的损害程度的%。
数字表示如下:
0%=无效(与未处理对照相似)
100%=全部损害
在此试验中,例如,以剂量125g/ha施用的制备实施例1的化合物,实际上完全杀死了多种杂草,例如对看麦娘(100%),野燕麦(100%),莎草(100%),狗尾草(100%),茼麻(100%),苋(100%),猪殃殃(100%),芥(100%)和苍耳(100%)。表A:苗前试验/温室活性成分 a.i.(g/ha)看麦娘 野燕麦 莎草 狗尾草 苘麻 苋 猪殃殃 芥 苍耳
(1) 125 100 100 100 100 100 100 100 100 100
实施例B
苗后试验
溶剂: 5重量份丙酮
乳化剂: 1重量份烷基芳基聚乙二醇醚
为了制备活性化合物的适合制剂,将1重量份的活性化合物与预定量的溶剂混合,加入预定量的乳化剂并用水稀释浓缩物得到所需浓度的处理液。
向株高5-15cm的供试植物喷雾活性化合物的制剂,以这种方式向每单位面积施用特定量的活性化合物。
三周后,与未处理对照物的发育比较,评价对植物的损害程度的%。数字表示如下:
0% =无效(与未处理对照相似)
100%=全部损害
在此试验中,例如,以剂量125g/ha施用的制备实施例1的化合物,实际上完全杀死了多种杂草,例如对看麦娘(100%),野燕麦(100%),莎草(100%),狗尾草(100%),茼麻(100%),苋(100%),猪殃殃(100%),芥(100%)和苍耳(100%)。
表B:苗后试验/温室活性成分 a.i.(g/ha)看麦娘 野燕麦 莎草 狗尾草 苘麻 苋 猪殃殃 芥 苍耳(1) 125 100 100 100 100 100 100 100 100 100
Claims (9)
1.通式(I)的取代的氨基尿嘧啶:
其中
Q代表O,S,SO或SO2,
R1代表氢,氰基或卤素,
R2代表氰基或硫代氨基甲酰基,
R3代表氢或代表分别可选择取代的烷基,链烯基,链炔基,环烷基,环烷基烷基,芳基,芳烷基,杂环基或杂环基烷基,
R4代表氢,卤素或代表分别可选择取代的烷基或烷氧基,
R5代表可选择取代的烷基,
R6代表氢或代表分别可选择取代的烷基,链烯基或链炔基,和
R7代表氢或代表分别可选择取代的烷基,链烯基或链炔基。
2.根据权利要求1的通式(I)取代的氨基尿嘧啶,其特征在于
Q代表O,S,SO或SO2,
R1代表氢,氰基,氟或氯,
R2代表氰基或硫代氨基甲酰基,
R3代表氢,代表各自可被氰基,羧基,氟,氯,溴或被C1-C4-烷氧基,C1-C4-烷基-羰基,C1-C4-烷氧基羰基或N-(C1-C4-烷基)-N-苯基-氨基羰基(各自可被氟和/或氯可选择取代)可选择取代的各自至多10碳原子的烷基,链烯基或链炔基,
R3还代表环烷基部分具有3至8碳原子的环烷基或环烷基烷基,且烷基部分可选择的至多4碳原子,每个基团可选择的被氰基,羧基,氟,氯,溴,或被C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷基-羰基或C1-C4-烷氧基-羰基取代,
R3还代表芳基部分具有6至10碳原子的芳基或芳烷基,且烷基部分可选择的至多4碳原子,每个基团可选择的被氰基,羧基,硝基,氨基甲酰基,硫代氨基甲酰基,氟,氯,溴,被C1-C4-烷基,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-羰基或C1-C4-烷氧基-羰基(各自可被氟和/或氯可选择取代),被苯基,苯氧基或苯硫基(各自可被氟,氯,溴,氰基,甲基,甲氧基,三氟甲基和/或三氟甲氧基可选择取代)可选择取代,或
R3还代表呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,氧杂环丁烷,硫杂环丁烷(thietanyl),噁唑基,异噁唑基,噻唑基,噁二唑基,噻二唑基,吡唑基,吡啶基,嘧啶基,三嗪基,吲哚基,喹啉基或喹喔啉基,上述基团各自可选择的被氰基,羧基,氨基甲酰基,硫代氨基甲酰基,氟,氯,溴,被C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基亚磺酰基,C1-C4-烷磺酰基,C1-C4-烷基-羰基或C1-C4-烷氧基-羰基(各自可被氟和/或氯可选择取代),被苯基,苯氧基或苯硫基(各自可被氟,氯,溴,氰基,甲基,甲氧基,三氟甲基和/或三氟甲氧基可选择取代)可选择取代,
R4代表氢,氟,氯,溴或代表分别可选择氟-和/或氯-取代的各自具有1至4碳原子的烷基或烷氧基,
R5代表可选择氟-和/或氯-取代的各自具有1至4碳原子的烷基,
R6代表氢或代表分别可选择氟-,氯-或C1-C4-烷氧基-取代的各自至多具有6碳原子的烷基,链烯基或链炔基,和
R7代表氢或代表分别可选择氟-,氯-或C1-C4-烷氧基-取代的各自至多具有6碳原子的烷基,链烯基或链炔基。
3.根据权利要求1的通式(I)取代的氨基尿嘧啶,其特征在于
Q代表O,S,SO或SO2,
R1代表氢,氟或氯,
R2代表氰基或硫代氨基甲酰基,
R3代表氢,代表分别可选择氰基-,羧基-,氟-,氯-,甲氧基-,乙氧基-,正-或异-丙氧基,乙酰基-,丙酰基-,甲氧基羰基-,乙氧基羰基-,正-或异-丙氧基羰基-取代的甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基-,正-,异-,仲-或叔-戊基,丙烯基,丁烯基,戊烯基,丙炔基,丁炔基或戊炔基,代表分别可选择氰基-,羧基-,氟-,氯-,溴-,甲基-,乙基-,正-或异-丙基,甲氧基-,乙氧基-,正-或异-丙氧基-,乙酰基-或丙酰基-,甲氧基羰基-,乙氧基羰基-,正-或异-丙氧基羰基-取代的环丙基,环丁基,环戊基,环己基,环丙基甲基,环丁基甲基,环戊基甲基或环己基甲基,代表分别可选择氰基-,羧基-,硝基-,氨基甲酰基-,硫代氨基甲酰基-,氟-,氯-,溴-,甲基-,乙基-,正-或异-丙基,正-,异-,仲-或叔-丁基-,三氟甲基-,甲氧基-,乙氧基-,正-或异-丙氧基-,甲硫基-,乙硫基-,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-,甲氧基羰基-,乙氧基羰基-,正-或异-丙氧基羰基-取代的苯基,苄基或苯乙基,或代表分别可选择氰基-,羧基-,氨基甲酰基-,硫代氨基甲酰基-,氟-,氯-,溴-,甲基-,乙基-,正-或异-丙基-,甲氧基-,乙氧基-,正-或异-丙氧基-,甲硫基-,乙硫基-,甲基亚磺酰基-,乙基亚磺酰基-,甲磺酰基,乙磺酰基,乙酰基-,丙酰基-,甲氧基羰基-,乙氧基羰基-,正-或异-丙氧基羰基-,苯基-,苯氧基-或苯硫基-取代的呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,氧杂环丁烷,硫杂环丁烷,噁唑基,异噁唑基,噻唑基,噁二唑基,噻二唑基,吡唑基,吡啶基,嘧啶基,三嗪基,吲哚基,喹啉基或喹喔啉基,
R4代表氢,氟,氯,溴或甲基,
R5代表甲基,乙基,二氟甲基,二氯甲基,三氟甲基,三氯甲基,氯二氟甲基,氟二氯甲基,氯乙基,氟乙基,二氯乙基,二氟乙基,氯氟乙基,氯二氟乙基,氟二氯乙基,三氟乙基,四氟乙基,氯三氟乙基或五氟乙基,
R6代表氢或代表分别可选择氟-,氯-,甲氧基-,或乙氧基-取代的甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,丙烯基,丁烯基,丙炔基或丁炔基,和
R7代表氢或代表分别可选择氟-,氯-,甲氧基-,或乙氧基-取代的甲基,乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,丙烯基,丁烯基,丙炔基或丁炔基。
其中
Q,R1,R2,R4,R5,R6和R7如权利要求1中的定义,
其特征在于
其中
Q,R1,R2,R3,R4和R5各自为上述定义
或
(b)通式(Ia)的氨基尿嘧啶与硫化氢,如果适合,在反应助剂存在下,和如果适合,在稀释剂存在下反应而制备,
其中
Q,R1,R3,R4,R5,R6和R7各自为上述定义
或
其中
Q,R1,R2,R3,R4和R5各自为上述定义,
X-R7(IIIa) X-R8(IIIb)
其中
R7,和R8各自为上述定义和
X代表卤素或基团-O-SO2-O-R7或-O-SO2-O-R8,
或
R1,R2,R4,R5,R6和R7各自为上述定义
X代表卤素,
M-Q-R3 (V)
其中
Q和R3各自为上述定义和
M代表氢或金属等价物。
5.通式(Ia)的氨基尿嘧啶:
其中
Q代表O,S,SO或SO2,
R1代表氢,氰基或卤素,
R3代表氢或代表分别可选择取代的烷基,链烯基,链炔基,环烷基,环烷基烷基,芳基,芳烷基,杂环基或杂环基烷基,
R4代表氢,卤素或分别代表可选择取代的烷基或烷氧基,
R5代表可选择取代的烷基,
R6代表氢或分别代表可选择取代的烷基,链烯基或链炔基,和
R7代表氢或分别代表可选择取代的烷基,链烯基或链炔基。
6.除草剂,其特征在于包含至少一种根据权利要求1至4的通式(I)的取代氨基尿嘧啶。
7.防治有害植物的方法,其特征在于使根据权利要求1至4的通式(I)的取代氨基尿嘧啶作用于有害植物和/或其生长地。
8.根据权利要求1-4的通式(I)的取代氨基尿嘧啶防治有害植物的用途。
9.除草剂的制备方法,其特征在于将根据权利要求1-4的通式(I)的取代氨基尿嘧啶与填充剂和/或表面活性剂混合。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19527570A DE19527570A1 (de) | 1995-07-28 | 1995-07-28 | Substituierte Aminouracile |
DE19527570.5 | 1995-07-28 |
Publications (1)
Publication Number | Publication Date |
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CN1196725A true CN1196725A (zh) | 1998-10-21 |
Family
ID=7767991
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN96197016A Pending CN1196725A (zh) | 1995-07-28 | 1996-07-15 | 取代的氨基尿嘧啶 |
Country Status (11)
Country | Link |
---|---|
US (1) | US6417141B1 (zh) |
EP (1) | EP0842155B1 (zh) |
JP (1) | JP4135973B2 (zh) |
CN (1) | CN1196725A (zh) |
AR (1) | AR002880A1 (zh) |
AU (1) | AU6656696A (zh) |
BR (1) | BR9609671A (zh) |
CA (1) | CA2227762C (zh) |
DE (2) | DE19527570A1 (zh) |
ES (1) | ES2192610T3 (zh) |
WO (1) | WO1997005116A1 (zh) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
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DE19627901A1 (de) * | 1996-07-11 | 1998-01-15 | Bayer Ag | Substituierte aromatische Carbonylverbindungen und ihre Derivate |
US6333296B1 (en) * | 1997-03-14 | 2001-12-25 | Isk Americas Incorporated | Diaryl ethers and processes for their preparation and herbicidal and desiccant compositions containing them |
DE19728125A1 (de) * | 1997-07-02 | 1999-01-07 | Bayer Ag | Substituierte Aryluracile |
US6780821B1 (en) | 1998-07-09 | 2004-08-24 | Bayer Aktiengesellschaft | Substituted phenyl uracils |
IL139899A (en) | 1999-12-07 | 2005-06-19 | Sumitomo Chemical Co | Uracil compounds and use thereof |
JP2001072668A (ja) | 1999-07-07 | 2001-03-21 | Sumitomo Chem Co Ltd | ウラシル化合物およびその用途 |
DE19954312A1 (de) * | 1999-11-11 | 2001-05-17 | Bayer Ag | Substituierte Phenyluracile |
IL167954A (en) | 2000-02-04 | 2007-10-31 | Sumitomo Chemical Co | History of pyrimidine |
US6403534B1 (en) | 2000-06-28 | 2002-06-11 | Sumitomo Chemical Company, Limited | Uracil compounds and use thereof |
RU2532104C2 (ru) | 2001-10-19 | 2014-10-27 | 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 |
WO2021063821A1 (en) | 2019-10-01 | 2021-04-08 | Bayer Aktiengesellschaft | Pyrimidinedione derivatives |
Family Cites Families (5)
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EP0438209B1 (en) * | 1990-01-18 | 1994-09-21 | Nissan Chemical Industries, Limited | Uracil derivatives and pesticides containing the same as active ingredient |
EP0517181B1 (en) | 1991-06-07 | 1995-09-20 | Sumitomo Chemical Company Limited | Amino uracil derivatives, and their production and use |
PT758324E (pt) | 1994-05-04 | 2005-07-29 | Bayer Cropscience Ag | Tiocarboxilamidas aromaticas substituidas e sua utilizacao como herbicidas |
DE19500439A1 (de) | 1994-05-04 | 1995-11-09 | Bayer Ag | Substituierte aromatische Thiocarbonsäureamide |
DE19504188A1 (de) * | 1995-02-09 | 1996-08-14 | Basf Ag | Neue 3-(4-Cyanophenyl)uracile |
-
1995
- 1995-07-28 DE DE19527570A patent/DE19527570A1/de not_active Withdrawn
-
1996
- 1996-07-15 CA CA002227762A patent/CA2227762C/en not_active Expired - Fee Related
- 1996-07-15 US US09/000,038 patent/US6417141B1/en not_active Expired - Fee Related
- 1996-07-15 DE DE59610332T patent/DE59610332D1/de not_active Expired - Fee Related
- 1996-07-15 ES ES96926347T patent/ES2192610T3/es not_active Expired - Lifetime
- 1996-07-15 CN CN96197016A patent/CN1196725A/zh active Pending
- 1996-07-15 AU AU66566/96A patent/AU6656696A/en not_active Abandoned
- 1996-07-15 EP EP96926347A patent/EP0842155B1/de not_active Expired - Lifetime
- 1996-07-15 BR BR9609671A patent/BR9609671A/pt not_active IP Right Cessation
- 1996-07-15 WO PCT/EP1996/003088 patent/WO1997005116A1/de active IP Right Grant
- 1996-07-15 JP JP50716397A patent/JP4135973B2/ja not_active Expired - Fee Related
- 1996-07-18 AR ARP960103641A patent/AR002880A1/es active IP Right Grant
Also Published As
Publication number | Publication date |
---|---|
DE19527570A1 (de) | 1997-01-30 |
ES2192610T3 (es) | 2003-10-16 |
AR002880A1 (es) | 1998-04-29 |
CA2227762A1 (en) | 1997-02-13 |
WO1997005116A1 (de) | 1997-02-13 |
AU6656696A (en) | 1997-02-26 |
EP0842155A1 (de) | 1998-05-20 |
EP0842155B1 (de) | 2003-04-09 |
JPH11510145A (ja) | 1999-09-07 |
US6417141B1 (en) | 2002-07-09 |
JP4135973B2 (ja) | 2008-08-20 |
DE59610332D1 (de) | 2003-05-15 |
CA2227762C (en) | 2009-04-28 |
BR9609671A (pt) | 1999-07-06 |
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