CN1193319A - 取代的羰基氨基苯基尿嘧啶类化合物 - Google Patents
取代的羰基氨基苯基尿嘧啶类化合物 Download PDFInfo
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- CN1193319A CN1193319A CN96196296A CN96196296A CN1193319A CN 1193319 A CN1193319 A CN 1193319A CN 96196296 A CN96196296 A CN 96196296A CN 96196296 A CN96196296 A CN 96196296A CN 1193319 A CN1193319 A CN 1193319A
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- alkyl
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- methyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 16
- -1 fluoro- Chemical class 0.000 claims description 139
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 45
- 239000000460 chlorine Substances 0.000 claims description 41
- 229910052801 chlorine Inorganic materials 0.000 claims description 41
- 229910052731 fluorine Inorganic materials 0.000 claims description 39
- 239000011737 fluorine Substances 0.000 claims description 39
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 37
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 25
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 25
- 229910052794 bromium Inorganic materials 0.000 claims description 25
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
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- 238000006243 chemical reaction Methods 0.000 claims description 11
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
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- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000005493 quinolyl group Chemical group 0.000 claims description 8
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 6
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- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 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
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 4
- 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 4
- 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 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical compound [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000006003 dichloroethyl group Chemical group 0.000 claims description 2
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 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
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 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
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 230000001473 noxious effect Effects 0.000 claims 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 3
- 241000196324 Embryophyta Species 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 14
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
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- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
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- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
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- 235000011056 potassium acetate 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
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
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- 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
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- 235000019355 sepiolite Nutrition 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
- 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
- 239000003516 soil conditioner Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
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- 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
- 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
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 1
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- 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 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
- 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
- 239000004563 wettable powder Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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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
-
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Abstract
本发明涉及通式(Ⅰ)的新的取代的羰基氨基苯基尿嘧啶及其制备和作为除草剂的应用。其中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羰基氨基苯基尿嘧啶类化合物,及其制备方法和作为除草剂的应用。
已知某些取代氨基苯基尿嘧啶类化合物具有除草性能(参考:EP 408382/US 5 084 084/US 5 127 935/US 5 154 755,EP 563 384/US 5 356863,EP 648 749)。可是,上述已有的化合物不具备明显的效果。
本发明提供了通式(I)的新的取代羰基氨基苯基尿嘧啶类化合物:
其中
R1代表氢,氰基或卤素,
R2代表氰基或卤素,
R3代表均可任选取代的环烷基,环烷基烷基,芳基,芳烷基,杂环基或杂环基烷基,
R4代表氢或代表均可任选取代的烷基,链烯基,炔基,环烷基,环烷基烷基,芳基,芳烷基,杂环基或杂环基烷基或代表基团-CO-R3,其中R3为上述定义,
R5代表氢,卤素或代表均可任选取代的烷基或烷氧基,
R6代表可任选取代的烷基和
R7代表氢或代表均可任选取代的烷基,烷氧基,链烯基或炔基。
通式(I)的新的取代氨基苯基尿嘧啶类化合物是通过合适的通式(II)氨基苯基尿嘧啶类化合物与通式(III)的酸衍生物,如果合适在反应助剂存在下和如果合适在稀释剂存在下反应而制备
其中
R1,R2,R4,R5,R6,和R7如上述定义和
R8代表氢,三氟乙酰基或烷基磺酰基,
R3-CO-X (III)
其中
R3如上述定义和
X代表卤素或基团-O-CO-R3。
新的通式(I)的取代羰基氨基苯基尿嘧啶类化合物具有很强的除草活性。式(II)的起始物也具有一定程度的除草活性。
在定义中,饱和或不饱和烃链,如烷基,链烯基或炔基,各自是直链或支链的。
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
R1代表氢,氰基,氟或氯,
R2代表氰基,氟,氯或溴,
R3代表均可任选由氰基-,氟-,氯-,溴-或C1-C4-烷基-取代的环烷基或环烷基烷基,其中在环烷基部分具有3至8个碳原子和任选在烷基部分具有1至4个碳原子,
R3还代表苯基,萘基,苄基,苯乙基,呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,噁唑基,异噁唑基,吡唑基,吡啶基或喹啉基,上述基团可任选被氟,氯,溴,氰基,硝基,羧基,氨基甲酰基,硫代氨基甲酰基,被C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(各自可任选被氟和/或氯取代),被二甲基氨基磺酰基或二乙基氨基磺酰基,被C1-C4-烷氧基羰基(其可任选被氟,氯,溴,氰基,甲氧基或乙氧基取代),被苯基,苯氧基或苯硫基(各自可任选被氟,氯,溴,氰基,甲基,甲氧基,三氟甲基和/或三氟甲氧基取代)取代,
R4代表氢,代表均可任选由氰基-,羧基-,氨基甲酰基-,硫代氨基甲酰基-,卤素-,C1-C4-烷基-或C1-C4-烷氧基羰基-取代的各自具有至多10个碳原子的烷基,链烯基或炔基,
R4还代表均可任选由氰基-,氟-,氯-,溴-或C1-C4-烷基-取代的环烷基或环烷基烷基,其中在环烷基部分具有3至8个碳原子和任选在烷基部分具有1至4个碳原子,
R4还代表苯基,萘基,苄基,苯乙基,呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,噁唑基,异噁唑基,吡唑基,吡啶基或喹啉基,上述基团可任选被氟,氯,溴,氰基,硝基,羧基,氨基甲酰基,硫代氨基甲酰基,被C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(各自可任选被氟和/或氯取代),被二甲基氨基磺酰基或二乙基氨基磺酰基,被C1-C4-烷氧基羰基(其可任选被氟,氯,溴,氰基,甲氧基或乙氧基取代),被苯基,苯氧基或苯硫基(各自可任选被氟,氯,溴,氰基,甲基,甲氧基,三氟甲基和/或三氟甲氧基取代)取代,或代表基团-CO-R3,其中R3具有上面指明的优选含意,
R5代表氢,氟,氯,溴或代表各自可任选由氟-和/或氯-取代的1至4个碳原子的烷基或烷氧基,
R6代表可任选由氟-和/或氯-取代的1至4个碳原子的烷基或烷氧基,
R7代表氢或代表均可任选由氰基-,氟-,氯-或C1-C4-烷氧基取代的至多6个碳原子的烷基,烷氧基,链烯基或炔基。
本发明特别提供式(I)化合物,其中:
R1代表氢,氟或氯,
R2代表氰基,氟,氯或溴,
R3代表均可任选由氰基-,氟-,氯-,溴-,甲基-,乙基-,正-或异-丙基取代的环丙基,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,
R3还代表苯基,萘基,苄基,苯乙基,呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,噁唑基,异噁唑基,吡唑基,吡啶基或喹啉基,上述基团可任选被氟,氯,溴,氰基,硝基,羧基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,三氟甲基,甲氧基,乙氧基,正-或异-丙氧基,二氟甲氧基,三氟甲氧基,甲硫基,乙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,被二甲基氨基磺酰基或二乙基氨基磺酰基,被甲氧基羰基,乙氧基羰基,正-或异-丙氧基羰基,被苯基,苯氧基或苯硫基取代,
R4代表氢,代表均可任选由氰基-,羧基-,氨基甲酰基-,硫代氨基甲酰基-,卤素-,C1-C4-烷基-或C1-C4-烷氧基羰基-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,
R4还代表均可任选由氰基-,氟-,氯-,溴-,甲基-,乙基-,正-或异丙基取代的环丙基,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,
R4还代表均可任选由氟-,氯-,溴-,氰基-,硝基-,羧基-,氨基甲酰基-,硫代氨基甲酰基-,甲基-,乙基-,正-或异丙基-,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-或乙基磺酰基-,二甲基氨基磺酰基-或二乙基氨基磺酰基-,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-取代的苯基,萘基,苄基,苯乙基,呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,噁唑基,异噁唑基,吡唑基,吡啶基或喹啉基,或代表基团-CO-R3,其中R3具有上面指明的特别优选的定义,
R5代表氢,氟,氯,溴,甲基,乙基,甲氧基或乙氧基,
R6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,氟乙基,氯乙基,二氟乙基,二氯乙基,氯氟乙基,三氟乙基,三氯乙基,氯二氟乙基,氟二氯乙基,四氟乙基,氯三氟乙基或五氟乙基和
R7代表氢或代表均可任选由氰基-,氟-,氯-,甲氧基-或乙氧基-取代的甲基,乙基,正-或异-丙基,正-,异-或仲-丁基,甲氧基,乙氧基,正-或异-丙氧基,正-,异-或仲-丁氧基,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,因此包括所指明的优选范围间的组合。
例如,应用1-(4-氯-2-氟-5-甲基磺酰基氨基-苯基)-3,6-二氢-2,6-二氧代-3,5-二甲基-4-二氟甲基-1(2H)-嘧啶和2-氟苯甲酰氯作为起始物,在根据本发明方法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)化合物的方法中用作起始物的氨基苯基尿嘧啶的一般定义。在式(II)中,R1,R2,R4,R5,R6,和R7各自优选或特别优选具有上文(关于意欲根据本发明制备的式(I)化合物的描述中)已经指明的那些对于R1,R2,R4,R5,R6,和R7而言是优选或特别优选的含意;R8优选代表氢,三氟乙酰基或C1-C4-烷基磺酰基。
式(II)的起始物是已知的或可以通过已知方法制备(参考:EP 408382,EP 648 749,制备实施例)。
式(III)提供了在根据本发明制备式(I)化合物的方法中,进一步用作起始物的酸衍生物的一般定义。在式(III)中,R3优选或特别优选具有上文(关于意欲根据本发明制备的式(I)化合物的描述中)已经指明的那些对于R3而言是优选或特别优选的含意;X优选代表氟,氯或溴,特别是氟。
式(III)的起始物是已知用于合成的化学品。
根据本发明制备式(I)化合物的方法优选在合适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(BDN),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)化合物的方法优选在稀释剂存在下进行。合适的稀释剂通常是常规的有机溶剂。它们优选的包括可任选卤代的脂肪族、脂环族和芳香烃,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-或叔-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醇醚、二甘醇单甲基醚或二甘醇单乙基醚;及其与水的混合物或纯粹只是水。
在根据本发明的方法中的反应温度可在相当宽的范围内变化。反应通常在0℃至150℃,优选10℃至120℃的温度下进行。
根据本发明的方法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。
进行根据本发明的方法时,在各种情况下通常使用大约等摩尔量的起始物。可是,在一些情况下,还可使其中的一种成分过量。通常,反应在反应助剂存在下的适合的稀释剂存在下进行,并在所需的反应温度下搅拌反应混合物数小时。在根据本发明的方法中,通过常规的方法进行后处理(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:
下列属的双子叶杂草: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,焊菜,水叶松,母草,野芝麻,婆婆纳,苘麻,刺果,曼陀罗,堇菜,鼬瓣花,罂粟,矢车菊,车轴草和毛茛。
下列属的双子叶作物: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。
下列属的单子叶杂草: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,狗牙根,鸭舌草,飘拂草,慈菇,针蔺,草,雀稗,鸭嘴草,尖瓣花,龙爪茅,剪股颍,看麦娘和风草。
下列属的单子叶作物: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,对其它植物它们也具有相同的作用。
根据其浓度,本发明活性化合物适合于灭生性地防治杂草,例如在工业区和铁道线,种树或没种树的路或广场。同样,本化合物还可用于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,浆果和啤酒花田,草皮,草地和牧草中防治杂草,并可选择性地在一年生栽培作物中防治杂草。
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,如液剂,乳剂,可湿性粉剂,悬浮剂,粉剂,细粉剂,糊剂,可溶性粉剂,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,以及无机和有机粉末的合成颗粒,和有机材料的颗粒如锯末,坚果壳,玉米穗轴和烟草茎;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。
可能使用的着色剂如无机颜料,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、铜、钼和锌的盐。
制剂中通常含有按重量计0.1%-95%,优选按重量计0.5%-90%的活性化合物。
在防治杂草时,也可以使用根据本发明的活性化合物(原样或其制剂形式)与已知除草剂的混合物,上述混合物可能是加工好的制剂或可能是桶混物。
上述混合物的适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;芳氧基链烷酸酯,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,如六嗪酮,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,氟咯草酮,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,弥雾或撒施。
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掺入土壤中。
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,用量为对每公顷土壤表面积使用10g至10kg活性化合物,优选50g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稀释实施例。
制备实施例:
实施例1
伴随搅拌,将1.3g(6mmol)的3,5-二氯苯甲酰氯加入到2.1g(5mmol)的1-(4-氰基-2-氟-5-乙基磺酰基氨基-苯基)-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶,1ml的三乙胺和50ml乙腈的混合物中,将反应混合物在20℃下搅拌24小时。然后用真空水泵浓缩混合物,剩余物在1N盐酸/乙酸乙酯中振荡,分离有机相,用硫酸钠干燥并过滤。用水泵浓缩滤液,剩余物用乙醚/石油醚消化,吸滤分离结晶产物。
得到0.90g(理论值的30%)的1-[4-氰基-2-氟-5-(3,5-二氯-苯甲酰氨基)-苯基]-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶],熔点212℃。
将1.67g(4mmol)的1-(4-氰基-2-氟-5-甲基磺酰基氨基-苯基)-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶,1.05g(5mmol)的三氟乙酸酐,1.5g的三乙胺和20ml的乙腈的混合物在20℃下搅拌30分钟,然后用真空水泵浓缩。剩余物在1N的盐酸/乙酸乙酯中振荡,分离出有机相,用硫酸钠干燥并过滤。用真空水泵浓缩滤液,剩余物用柱色谱处理(硅胶,己烷/乙酸乙酯,体积:4∶1)。
得到1.0g(理论值的59%)的1-(4-氰基-2-氟-5-三氟乙酰基氨基苯基]-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶,熔点105℃。
实施例(II-2)
将2.19g(5mmol)的1-(4-氰基-2-氟-5-三氟乙酰基氨基-苯基)-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶,0.76g(6mmol)的硫酸二甲酯,0.83g的碳酸钾和50ml的丙酮的混合物加热回流3小时,然后用真空水泵浓缩。剩余物在1N的盐酸/乙醚搅拌,然后吸滤分离结晶产物。
得到1.4g(理论值的64%)的1-[4-氰基-2-氟-5-(N-甲基-N-三氟乙酰基氨基)-苯基)-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶,熔点202℃。
伴随搅拌,将0.17g(1.2mmol)的新戊酰氯加入到0.50g(1.2mmol)的1-(4-氰基-2-氟-5-三氟乙酰基氨基-苯基)-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶,1ml的三乙胺和50ml的乙腈的混合物中,在20℃下搅拌18小时,在60℃下再搅拌15小时。然后用真空水泵浓缩混合物,剩余物在1N的盐酸/乙酸乙酯中振荡,分离出有机相,用硫酸钠干燥并过滤。用真空水泵浓缩滤液,剩余物用柱色谱处理(硅胶,氯仿/乙酸乙酯,体积:1∶1)。
除了未反应的1-(4-氰基-2-氟-5-三氟乙酰氨基-苯基)-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶(第一馏份0.30g),得到第二馏份的0.2g(理论值的50%)的1-(4-氰基-2-氟-5-氨基-苯基)-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶,熔点195℃。
根据实施例(II-3)制备的化合物是文献中未公开过的;作为新的化合物,它构成本申请主题物的一部分。
应用实施例:
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备物,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,用活性化合物的制备物浇水。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,与未处理对照的发育作比较,评价对植物的损害程度的%。
数字表示如下:
0%=无效(与未处理对照一样)
100%=全部损害
在此试验中,例如,在125g和4,000g施用量下,制备实施例1,2,3,4,(II-1)和(II-2)的化合物表现出极强的除草活性,例如对看麦娘(70-95%),野燕麦(80-100%),狗尾草(100%),苘麻(100%),苋(95-100%)和白芥(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备物,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备物,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,与未处理对照的发育作比较,评价对植物的损害程度的%。
数字表示如下:
0%=无效(与未处理对照一样)
100%=全部损害
在此试验中,例如,在125g至2,000g施用量下,制备实施例1,2,3,4,(II-1)和(II-2)的化合物表现出极强的除草活性,例如对苘麻(100%),苋(90-100%)和白芥(80-100%)。
Claims (10)
1.通式(I)的羰基氨基苯基尿嘧啶类化合物:
其中
R1代表氢,氰基或卤素,
R2代表氰基或卤素,
R3代表均可任选取代的环烷基,环烷基烷基,芳基,芳烷基,杂环基或杂环基烷基,
R4代表氢或代表均可任选选取代的烷基,链烯基,炔基,环烷基,环烷基烷基,芳基,芳烷基,杂环基或杂环基烷基或代表基团-CO-R3,其中R3如上述定义,
R5代表氢,卤素或代表均可任选取代的烷基或烷氧基,
R6代表可任选取代的烷基和
R7代表氢或代表均可选任取代的烷基,烷氧基,链烯基或炔基。
3.根据权利要求1的通式(I)羰基氨基苯基尿嘧啶类化合物,其特征在于
R1代表氢,氰基,氟或氯,
R2代表氰基,氟,氯或溴,
R3代表均可任选由氰基-,氟-,氯-,溴-或C1-C4-烷基-取代的环烷基或环烷基烷基,其中在环烷基部分具有3至8个碳原子和任选在烷基部分具有1至4个碳原子,
R3还代表苯基,萘基,苄基,苯乙基,呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,噁唑基,异噁唑基,吡唑基,吡啶基或喹啉基,上述基团可任选被氟,氯,溴,氰基,硝基,羧基,氨基甲酰基,硫代氨基甲酰基,被C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(各自可任选被氟和/或氯取代),被二甲基氨基磺酰基或二乙基氨基磺酰基,被C1-C4-烷氧基羰基(其可任选被氟,氯,溴,氰基,甲氧基或乙氧基取代),被苯基,苯氧基或苯硫基(各自可任选被氟,氯,溴,氰基,甲基,甲氧基,三氟甲基和/或三氟甲氧基取代)取代,
R4代表氢,代表均可任选由氰基-,羧基-,氨基甲酰基-,硫代氨基甲酰基-,卤素-,C1-C4-烷基-或C1-C4-烷氧基羰基-取代的各自具有至多10个碳原子的烷基,链烯基或炔基,
R4还代表均可任选由氰基-,氟-,氯-,溴-或C1-C4-烷基-取代的环烷基或环烷基烷基,其中在环烷基部分具有3至8个碳原子和任选在烷基部分具有1至4个碳原子,
R4还代表苯基,萘基,苄基,苯乙基,呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,噁唑基,异噁唑基,吡唑基,吡啶基或喹啉基,上述基团可任选被氟,氯,溴,氰基,硝基,羧基,氨基甲酰基,硫代氨基甲酰基,被C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(各自可任选被氟和/或氯取代),被二甲基氨基磺酰基或二乙基氨基磺酰基,被C1-C4-烷氧基羰基(其可任选被氟,氯,溴,氰基,甲氧基或乙氧基取代),被苯基,苯氧基或苯硫基(各自可任选被氟,氯,溴,氰基,甲基,甲氧基,三氟甲基和/或三氟甲氧基取代)取代,或代表基团-CO-R3,其中R3具有上面指明的优选的含意,
R5代表氢,氟,氯,溴或代表各自可任选由氟-和/或氯-取代的1至4个碳原子的烷基或烷氧基,
R6代表可任选由氟-和/或氯-取代的1至4个碳原子的烷基或烷氧基,
R7代表氢或代表均可任选由氰基-,氟-,氯-或C1-C4-烷氧基取代的至多6个碳原子的烷基,烷氧基,链烯基或炔基。
4.根据权利要求1的通式(I)的羰基氨基苯基尿嘧啶类化合物,其特征在于
R1代表氢,氟或氯,
R2代表氰基,氟,氯或溴,
R3代表均可任选由氰基-,氟-,氯-,溴-,甲基-,乙基-,正-或异-丙基取代的环丙基,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,
R3还代表苯基,萘基,苄基,苯乙基,呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,噁唑基,异噁唑基,吡唑基,吡啶基或喹啉基,上述基团可任选被氟,氯,溴,氰基,硝基,羧基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,三氟甲基,甲氧基,乙氧基,正-或异-丙氧基,二氟甲氧基,三氟甲氧基,甲硫基,乙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基或乙基磺酰基,被二甲基氨基磺酰基或二乙基氨基磺酰基,被甲氧基羰基,乙氧基羰基,正-或异-丙氧基羰基,被苯基,苯氧基或苯硫基取代,
R4代表氢,代表均可任选由氰基-,羧基-,氨基甲酰基-,硫代氨基甲酰基-,卤素-,C1-C4-烷基-或C1-C4-烷氧基羰基-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,
R4还代表均可任选由氰基-,氟-,氯-,溴-,甲基-,乙基-,正-或异丙基取代的环丙基,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,
R4还代表均可任选由氟-,氯,溴-,氰基-,硝基-,羧基-,氨基甲酰基-,硫代氨基甲酰基-,甲基-,乙基-,正-或异丙基-,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-或乙基磺酰基-,二甲基氨基磺酰基-或二乙基氨基磺酰基-,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-取代的苯基,萘基,苄基,苯乙基,呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,噁唑基,异噁唑基,吡唑基,吡啶基或喹啉基,或代表基团-CO-R3,其中R3具有上面指明的特别优选的含意,
R5代表氢,氟,氯,溴,甲基,乙基,甲氧基或乙氧基,
R6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,氟乙基,氯乙基,二氟乙基,二氯乙基,氯氟乙基,三氟乙基,三氯乙基,氯二氟乙基,氟二氯乙基,四氟乙基,氯三氟乙基或五氟乙基和
R7代表氢或代表任选由氰基-,氟-,氯-,甲氧基-,或乙氧基-取代的甲基,乙基,正-或异-丙基,正-,异-或仲-丁基,甲氧基,乙氧基,正-或异-丙氧基,正-,异-或仲-丁氧基,丙烯基,丁烯基,丙炔基或丁炔基。
5.除草剂,其特征在于含有至少一种根据权利要求1至4的通式(I)的羰基氨基苯基尿嘧啶类化合物。
6.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)的羰基氨基苯基尿嘧啶类化合物作用于有害植物和/或其生长地。
7.根据权利要求1-4的通式(I)的羰基氨基苯基尿嘧啶类化合物防治有害植物的应用。
8.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)的羰基氨基苯基尿嘧啶类化合物与填充剂和/或表面活性剂混合。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE19523640A DE19523640A1 (de) | 1995-06-29 | 1995-06-29 | Substituierte Carbonylaminophenyluracile |
DE19523640.8 | 1995-06-29 |
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CN1193319A true CN1193319A (zh) | 1998-09-16 |
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CN96196296A Pending CN1193319A (zh) | 1995-06-29 | 1996-06-17 | 取代的羰基氨基苯基尿嘧啶类化合物 |
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EP (1) | EP0835247A1 (zh) |
JP (1) | JPH11508545A (zh) |
KR (1) | KR19990028225A (zh) |
CN (1) | CN1193319A (zh) |
AR (2) | AR002596A1 (zh) |
AU (1) | AU6304396A (zh) |
BR (1) | BR9609319A (zh) |
CA (1) | CA2225828A1 (zh) |
DE (1) | DE19523640A1 (zh) |
WO (1) | WO1997001542A1 (zh) |
Cited By (2)
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CN101165057B (zh) * | 2006-10-19 | 2011-04-27 | 湖南化工研究院 | 除草的n3-取代苯基脲嘧啶类化合物 |
CN101704790B (zh) * | 2006-10-19 | 2011-09-28 | 湖南化工研究院 | 除草的n3-取代苯基脲嘧啶类化合物 |
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US6077812A (en) | 1997-02-26 | 2000-06-20 | Fmc Corporation | Cycloimido-substituted benzofused heterocyclic herbicides |
DE19830694A1 (de) * | 1998-07-09 | 2000-01-13 | Bayer Ag | Substituierte Acylaminophenyl-uracile |
IL139899A (en) | 1999-12-07 | 2005-06-19 | Sumitomo Chemical Co | Uracil compounds and use thereof |
IL141034A0 (en) | 2000-02-04 | 2002-02-10 | Sumitomo Chemical Co | Uracil compounds and use thereof |
MY138097A (en) * | 2000-03-22 | 2009-04-30 | Du Pont | Insecticidal anthranilamides |
CN111065383A (zh) | 2017-07-11 | 2020-04-24 | 沃泰克斯药物股份有限公司 | 用作钠通道调节剂的羧酰胺 |
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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 |
-
1995
- 1995-06-29 DE DE19523640A patent/DE19523640A1/de not_active Withdrawn
-
1996
- 1996-06-17 KR KR1019970709536A patent/KR19990028225A/ko not_active Application Discontinuation
- 1996-06-17 JP JP9504139A patent/JPH11508545A/ja active Pending
- 1996-06-17 WO PCT/EP1996/002612 patent/WO1997001542A1/de not_active Application Discontinuation
- 1996-06-17 AU AU63043/96A patent/AU6304396A/en not_active Abandoned
- 1996-06-17 CN CN96196296A patent/CN1193319A/zh active Pending
- 1996-06-17 BR BR9609319A patent/BR9609319A/pt not_active Application Discontinuation
- 1996-06-17 CA CA002225828A patent/CA2225828A1/en not_active Abandoned
- 1996-06-17 EP EP96922007A patent/EP0835247A1/de not_active Withdrawn
- 1996-06-25 AR ARP960103312A patent/AR002596A1/es unknown
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1997
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101165057B (zh) * | 2006-10-19 | 2011-04-27 | 湖南化工研究院 | 除草的n3-取代苯基脲嘧啶类化合物 |
CN101704790B (zh) * | 2006-10-19 | 2011-09-28 | 湖南化工研究院 | 除草的n3-取代苯基脲嘧啶类化合物 |
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BR9609319A (pt) | 1999-07-06 |
AR006084A1 (es) | 1999-08-11 |
DE19523640A1 (de) | 1997-01-02 |
JPH11508545A (ja) | 1999-07-27 |
CA2225828A1 (en) | 1997-01-16 |
KR19990028225A (ko) | 1999-04-15 |
AR002596A1 (es) | 1998-03-25 |
EP0835247A1 (de) | 1998-04-15 |
AU6304396A (en) | 1997-01-30 |
WO1997001542A1 (de) | 1997-01-16 |
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