CN1129517A - 基于芳基尿嘧啶类的用于水稻栽培中的除莠剂 - Google Patents
基于芳基尿嘧啶类的用于水稻栽培中的除莠剂 Download PDFInfo
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- CN1129517A CN1129517A CN95116184A CN95116184A CN1129517A CN 1129517 A CN1129517 A CN 1129517A CN 95116184 A CN95116184 A CN 95116184A CN 95116184 A CN95116184 A CN 95116184A CN 1129517 A CN1129517 A CN 1129517A
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- 235000007164 Oryza sativa Nutrition 0.000 title claims abstract description 19
- 235000009566 rice Nutrition 0.000 title claims abstract description 19
- 239000004009 herbicide Substances 0.000 title claims description 10
- 240000007594 Oryza sativa Species 0.000 title abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 86
- 241000196324 Embryophyta Species 0.000 claims abstract description 22
- -1 aryl thiourea pyrimidine Chemical compound 0.000 claims description 249
- 239000000460 chlorine Substances 0.000 claims description 60
- 229910052801 chlorine Inorganic materials 0.000 claims description 60
- 239000011737 fluorine Substances 0.000 claims description 60
- 229910052731 fluorine Inorganic materials 0.000 claims description 60
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 57
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 56
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 239000001257 hydrogen Substances 0.000 claims description 49
- 150000002431 hydrogen Chemical class 0.000 claims description 46
- 229910052760 oxygen Inorganic materials 0.000 claims description 41
- 239000001301 oxygen Substances 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 40
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 34
- 229910052794 bromium Inorganic materials 0.000 claims description 34
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 30
- 239000005864 Sulphur Substances 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 230000002363 herbicidal effect Effects 0.000 claims description 28
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 28
- 230000000694 effects Effects 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 150000001721 carbon Chemical group 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- NXQDBZGWYSEGFL-UHFFFAOYSA-N Anilofos Chemical compound COP(=S)(OC)SCC(=O)N(C(C)C)C1=CC=C(Cl)C=C1 NXQDBZGWYSEGFL-UHFFFAOYSA-N 0.000 claims description 12
- DXXVCXKMSWHGTF-UHFFFAOYSA-N Chlomethoxyfen Chemical compound C1=C([N+]([O-])=O)C(OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 DXXVCXKMSWHGTF-UHFFFAOYSA-N 0.000 claims description 12
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 150000001924 cycloalkanes Chemical class 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 10
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
- 150000001336 alkenes Chemical class 0.000 claims description 8
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 8
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 8
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 8
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 7
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000004306 triazinyl group Chemical group 0.000 claims description 7
- GVROBYMTUJVBJZ-UHFFFAOYSA-N 1-(3-methylphenyl)-5-phenyl-1,2,4-triazole-3-carboxamide Chemical compound CC1=CC=CC(N2C(=NC(=N2)C(N)=O)C=2C=CC=CC=2)=C1 GVROBYMTUJVBJZ-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 6
- BDQWWOHKFDSADC-UHFFFAOYSA-N 2-(2,4-dichloro-3-methylphenoxy)-n-phenylpropanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C)OC1=CC=C(Cl)C(C)=C1Cl BDQWWOHKFDSADC-UHFFFAOYSA-N 0.000 claims description 6
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 claims description 6
- 239000005469 Azimsulfuron Substances 0.000 claims description 6
- QGQSRQPXXMTJCM-UHFFFAOYSA-N Benfuresate Chemical compound CCS(=O)(=O)OC1=CC=C2OCC(C)(C)C2=C1 QGQSRQPXXMTJCM-UHFFFAOYSA-N 0.000 claims description 6
- RRNIZKPFKNDSRS-UHFFFAOYSA-N Bensulide Chemical compound CC(C)OP(=S)(OC(C)C)SCCNS(=O)(=O)C1=CC=CC=C1 RRNIZKPFKNDSRS-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- JDWQITFHZOBBFE-UHFFFAOYSA-N Benzofenap Chemical compound C=1C=C(Cl)C(C)=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=C(C)C=C1 JDWQITFHZOBBFE-UHFFFAOYSA-N 0.000 claims description 6
- 239000005484 Bifenox Substances 0.000 claims description 6
- OEYOMNZEMCPTKN-UHFFFAOYSA-N Butamifos Chemical compound CCC(C)NP(=S)(OCC)OC1=CC(C)=CC=C1[N+]([O-])=O OEYOMNZEMCPTKN-UHFFFAOYSA-N 0.000 claims description 6
- WMLPCIHUFDKWJU-UHFFFAOYSA-N Cinosulfuron Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(OC)=N1 WMLPCIHUFDKWJU-UHFFFAOYSA-N 0.000 claims description 6
- VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 claims description 6
- OFSLKOLYLQSJPB-UHFFFAOYSA-N Cyclosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)C2CC2)=N1 OFSLKOLYLQSJPB-UHFFFAOYSA-N 0.000 claims description 6
- 239000005502 Cyhalofop-butyl Substances 0.000 claims description 6
- TYIYMOAHACZAMQ-CQSZACIVSA-N Cyhalofop-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C#N)C=C1F TYIYMOAHACZAMQ-CQSZACIVSA-N 0.000 claims description 6
- YUBJPYNSGLJZPQ-UHFFFAOYSA-N Dithiopyr Chemical compound CSC(=O)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=O)SC)=C1CC(C)C YUBJPYNSGLJZPQ-UHFFFAOYSA-N 0.000 claims description 6
- BXEHUCNTIZGSOJ-UHFFFAOYSA-N Esprocarb Chemical compound CC(C)C(C)N(CC)C(=O)SCC1=CC=CC=C1 BXEHUCNTIZGSOJ-UHFFFAOYSA-N 0.000 claims description 6
- ICWUMLXQKFTJMH-UHFFFAOYSA-N Etobenzanid Chemical compound C1=CC(OCOCC)=CC=C1C(=O)NC1=CC=CC(Cl)=C1Cl ICWUMLXQKFTJMH-UHFFFAOYSA-N 0.000 claims description 6
- 239000005567 Imazosulfuron Substances 0.000 claims description 6
- NAGRVUXEKKZNHT-UHFFFAOYSA-N Imazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N3C=CC=CC3=NC=2Cl)=N1 NAGRVUXEKKZNHT-UHFFFAOYSA-N 0.000 claims description 6
- SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005574 MCPA Substances 0.000 claims description 6
- AZFKQCNGMSSWDS-UHFFFAOYSA-N MCPA-thioethyl Chemical compound CCSC(=O)COC1=CC=C(Cl)C=C1C AZFKQCNGMSSWDS-UHFFFAOYSA-N 0.000 claims description 6
- 239000005575 MCPB Substances 0.000 claims description 6
- 101150039283 MCPB gene Proteins 0.000 claims description 6
- WDNYKBHZRADJAH-UHFFFAOYSA-N NN1N(N=NC1=O)C=O Chemical compound NN1N(N=NC1=O)C=O WDNYKBHZRADJAH-UHFFFAOYSA-N 0.000 claims description 6
- LVKTWOXHRYGDMM-UHFFFAOYSA-N Naproanilide Chemical compound C=1C=C2C=CC=CC2=CC=1OC(C)C(=O)NC1=CC=CC=C1 LVKTWOXHRYGDMM-UHFFFAOYSA-N 0.000 claims description 6
- UNLYSVIDNRIVFJ-UHFFFAOYSA-N Piperophos Chemical compound CCCOP(=S)(OCCC)SCC(=O)N1CCCCC1C UNLYSVIDNRIVFJ-UHFFFAOYSA-N 0.000 claims description 6
- YLPGTOIOYRQOHV-UHFFFAOYSA-N Pretilachlor Chemical compound CCCOCCN(C(=O)CCl)C1=C(CC)C=CC=C1CC YLPGTOIOYRQOHV-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- BGNQYGRXEXDAIQ-UHFFFAOYSA-N Pyrazosulfuron-ethyl Chemical compound C1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OCC BGNQYGRXEXDAIQ-UHFFFAOYSA-N 0.000 claims description 6
- KDWQYMVPYJGPHS-UHFFFAOYSA-N Thenylchlor Chemical compound C1=CSC(CN(C(=O)CCl)C=2C(=CC=CC=2C)C)=C1OC KDWQYMVPYJGPHS-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- MAHPNPYYQAIOJN-UHFFFAOYSA-N azimsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C2=NN(C)N=N2)C)=N1 MAHPNPYYQAIOJN-UHFFFAOYSA-N 0.000 claims description 6
- PPWBRCCBKOWDNB-UHFFFAOYSA-N bensulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)CC=2C(=CC=CC=2)C(O)=O)=N1 PPWBRCCBKOWDNB-UHFFFAOYSA-N 0.000 claims description 6
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- FUHMZYWBSHTEDZ-UHFFFAOYSA-M bispyribac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C([O-])=O)=N1 FUHMZYWBSHTEDZ-UHFFFAOYSA-M 0.000 claims description 6
- WZDDLAZXUYIVMU-UHFFFAOYSA-N bromobutide Chemical compound CC(C)(C)C(Br)C(=O)NC(C)(C)C1=CC=CC=C1 WZDDLAZXUYIVMU-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
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 claims description 6
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 6
- 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 6
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- BWUPSGJXXPATLU-UHFFFAOYSA-N dimepiperate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=O)N1CCCCC1 BWUPSGJXXPATLU-UHFFFAOYSA-N 0.000 claims description 6
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 6
- QMTNOLKHSWIQBE-FGTMMUONSA-N exo-(+)-cinmethylin Chemical compound O([C@H]1[C@]2(C)CC[C@@](O2)(C1)C(C)C)CC1=CC=CC=C1C QMTNOLKHSWIQBE-FGTMMUONSA-N 0.000 claims description 6
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 claims description 6
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 claims description 6
- HZDIJTXDRLNTIS-DAXSKMNVSA-N n-[[(z)-but-2-enoxy]methyl]-2-chloro-n-(2,6-diethylphenyl)acetamide Chemical compound CCC1=CC=CC(CC)=C1N(COC\C=C/C)C(=O)CCl HZDIJTXDRLNTIS-DAXSKMNVSA-N 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 claims description 6
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 claims description 6
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 6
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
- 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 claims description 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 5
- IKYICRRUVNIHPP-UHFFFAOYSA-N Dimethametryn Chemical compound CCNC1=NC(NC(C)C(C)C)=NC(SC)=N1 IKYICRRUVNIHPP-UHFFFAOYSA-N 0.000 claims description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
- 150000001345 alkine derivatives Chemical class 0.000 claims description 5
- 150000003851 azoles Chemical class 0.000 claims description 5
- 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 5
- 238000000034 method Methods 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 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 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- NNYRZQHKCHEXSD-UHFFFAOYSA-N Daimuron Chemical compound C1=CC(C)=CC=C1NC(=O)NC(C)(C)C1=CC=CC=C1 NNYRZQHKCHEXSD-UHFFFAOYSA-N 0.000 claims description 4
- 125000006323 alkenyl amino group Chemical group 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
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 4
- HFEJHAAIJZXXRE-UHFFFAOYSA-N cafenstrole Chemical compound CCN(CC)C(=O)N1C=NC(S(=O)(=O)C=2C(=CC(C)=CC=2C)C)=N1 HFEJHAAIJZXXRE-UHFFFAOYSA-N 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 4
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 4
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 4
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
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Classifications
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明涉及新的除莠协同活性化合物组合体,它由已知的芳基尿嘧啶(或芳基硫尿嘧啶,或这些芳基尿嘧啶或芳基硫尿嘧啶的异构化合物)和属于其它类别的其它已知除莠剂组成,可特别成功地用于水稻栽培中的选择性杂草防治。
Description
本发明涉及新的除莠协同活性化合物的组合体,该组合体一方面含有已知的芳基尿嘧啶类(或芳基硫尿嘧啶类,或这些芳基尿嘧啶类或芳基硫尿嘧啶类的异构化合物),另一方面还含有已知的属于其它物质类别的除莠剂,该组合体能特别成功地用于在水稻栽培中选择性地防治杂草。
芳基尿嘧啶类(或芳基硫尿嘧啶类)由于是具有广谱活性的除莠剂,因此是许多专利申请的主题(参见WO-A91/00278,US4979982,US5169430,EP-A408382,EP-A563384,US5084084,US5127935,US5154755,DE4327743,DE-4343451,DE4414326)。但已知的芳基尿嘧啶类(或芳基(硫)尿嘧啶类)对一些杂草、尤其是对单子叶植物杂草不起作用。
令人惊异的是,现已发现许多已知的来自芳基尿嘧啶类(或芳基硫尿嘧啶类,或者芳基尿嘧啶类或芳基硫尿嘧啶类的异构化合物)的除莠活性化合物与已知的除莠活性化合物例如来自氨甲酰基四唑啉酮类的除莠活性化合物和/或来自已作为除莠剂应用于水稻中的一系列化合物的活性化合物合用,对抗杂草能显示出显著的协同作用,并且可非常有利地作为具有广谱活性的组合体制剂用于在水稻栽培中在出苗前和出苗后选择性防治单子叶植物杂草和双子叶植物杂草。
本发明涉及协同除莠组合物,其特征在于:活性化合物组合体的活性组分包括:(I)通式(I)芳基尿嘧啶或芳基硫尿嘧啶或其异构化合物——通式(Ia)芳基尿嘧啶或芳基硫尿嘧啶在式(I)和(Ia)中,Q1代表氧或硫,Q2代表氧或硫,R1代表氢或卤素,R2代表卤素或氰基,R3代表-A1-A2-A3基团,其中A1代表单键、氧、硫、-SO-、-SO2-、-CO-或基团-N-A4-
,其中A4代表氢、羟基、烷基、烷氧基、芳基、烷基磺酰基或
芳基磺酰基,或(A1)代表烷二基、链烯二基、氮杂链烯二基
(azaalkenediyl)、炔二基、环烷二基、环烯二基或亚芳基,
它们各自均可被可选地取代,A2代表单键、氧、硫、-AO-、-SO2-、-CO-或基团-N-A4-,其中A4代表氢、烷基、芳基、烷基羰基、烷基磺酰基或芳基
磺酰基,或(A2)代表烷二基、链烯二基、氮杂链烯二基、炔
二基、环烷二基、环烯二基或亚芳基,它们各自均可被可选地
取代,A3代表氢、羟基、巯基、氨基、氰基、异氰基、氰硫基、硝基、
羧基、氨基甲酰基、硫代氨基甲酰基、磺基、氯磺酰基、卤素
,或烷基、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、烷氧基羰基、二烷氧(硫)基磷酰基、
链烯基、链烯氧基、链烯基氨基、烷叉氨基(alkylidenamino)
、链烯氧基羰基、炔基、炔氧基、炔基氨基、炔氧基羰基、环
烷基、环烷氧基、环烷基烷基、环烷基烷氧基、环烷叉氨基、
环烷氧羰基、环烷基烷氧基羰基、芳基、芳氧基、芳基烷基、
芳基烷氧基、芳氧基羰基、芳基烷氧基羰基、杂环基、杂环基
烷基、杂环基烷氧基或杂环基烷氧基羰基,它们各自均可被可
选地取代,R4代表氢、卤素或可选地被取代的烷基,R5代表氢、卤素或可选地被取代的烷基,和R6代表氢、羟基、氨基,或烷基、烷氧基、链烯基或炔基,它们各
自均可被可选地取代,
(“第1类活性化合物”)和(2)一种或多种来自第2类除莠剂的除莠活性化合物(“第2类活性
化合物”),包含下述类型的活性化合物(a)和/或(b):
(a)通式(II)氨基甲酰基四唑啉酮
式中R7和R8相同或不同,各自互相独立地代表氢或来自下列的一组
基团的基团:烷基、链烯基、炔基、环烷基、环烯基、环烷
基烷基、芳基和芳基烷基,这些基团各自均可被可选地取代,
和R9代表来自下列的一组基团的基团:烷基、链烯基、炔基、环
烷基、环烯基、环烷基烷基、芳基、芳基烷基、杂环基和杂
环基烷基,它们各自均可被可选地取代,(b)来自下列的水稻除莠剂(“通用名”或“代号”):cyclosulfamuron,AKD-741,amiprophos(-methyl),anilofos,benfuresate,bensulfuron (-methyl),地散磷,噻草平,杀草丹(thiobencarb),benzofenap,治草醚,bromobutide,去草安,butamifos,butenachlor,cafenstrole,chlormethoxynil,chlomitrofen,cinmethylin,CL-303569,CL-303578,cinosulfuron,clomeprop,2,4-D,cyhalofop-butyl,dimepiperate,dimethametryn,dithiopyr,azimsulfuron,dymron(daimuron),esprocarb,GS-32911,HOE-404,HOE-30374,HOK-7501,etobenzanid,imazosulfuron,cumyluron,KIH-911(KUH-911),KIH920(KUH920),triazofenamide,KPP-314,MCPA,MCPB,mefenacet,草达灭,NC-310,NC-311,naproanilide,除草醚,thenylchlor,恶草灵,piperophos,pretilachlor,扑草净,敌稗,pyrazolate,pyrazosulfuron (-ethyl),pyrazoxyfen,pyributicarb,quinclorac,西草净,氟乐灵和X-52,其中,在各种情况下,1重量份第1类活性化合物一般配以0.001-1000重量份第2类活性化合物。
特别有意义的本发明除莠组合物是含有以下组分的本发明除莠组合物:(I)上述式(I)或(Ia)化合物,其中Q1代表氧或硫,Q2代表氧或硫,R1代表氢、氟、氯或溴,R2代表氟、氯、溴、碘或氰基,R3代表-A1-A2-A3基团,其中,A1代表单键、氧、硫、-SO-、-SO2-、-CO-或基团-N-A4-,其
中A4代表氢、羟基、C1-C4烷基、C1-C4烷氧基、苯基、C1-C4
烷基磺酰基或苯基磺酰基,或(A1)代表C1-C6烷二基、C2-C6
链烯二基、C2-C6氮杂链烯二基、C2-C6炔二基、C3-C6环烷二
基、C3-C6环烯二基或亚苯基,它们各自均可被氟、氯或溴可选
地取代,A2代表单键、氧、硫、-SO-、-SO2-、-CO-或基团-N-A4-,其
中A4代表氢、羟基、C1-C4烷基、C1-C4烷氧基、苯基、C1-C4
烷基磺酰基或苯基磺酰基,或(A2)代表C1-C6烷二基、C2-C6
链烯二基、C2-C6氮杂链烯二基、C2-C6炔二基、C3-C6环烷二
基、C3-C6环烯二基或亚苯基,它们各自均可被氟、氯或溴可选
地取代,A3代表氢,羟基,氨基,氰基,异氰基,氰硫基,硝基,羧基,氨
基甲酰基,硫代氨基甲酰基,磺基,氯磺酰基,囟素;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,烷氧基羰基或二烷氧(硫)基磷酰基,它们在烷基部分各
具有1-6个碳原子,并均可被囟素或C1-C4烷氧基可选地取代;
链烯基,链烯氧基,链烯基氨基,烷叉氨基,链烯氧基羰基,炔基,炔氧基,炔基氨基或炔氧基羰基,它们在所述链烯基、烷叉
或炔基部分各具有2-6个碳原子,并均可被卤素可选地取代;环
烷基,环烷氧基,环烷基烷基,环烷基烷氧基,环烷叉氨基,环
烷氧基羰基或环烷基烷氧基羰基,它们在所述环烷基部分各具有
3-6个碳原子并可选地在所述烷基部分具有1-4个碳原子,并均可
被卤素、氰基、羧基、C1-C4烷基和/或C1-C4烷氧基羰基可选
地取代;或苯基,苯氧基,苯基-C1-C4烷基,苯基-C1-C4烷
氧基,苯氧基羰基或苯基-C1-C4烷氧基羰基,(在每种情况下
均可选地完全或部分氢化的)吡咯基,吡唑基,咪唑基,三唑基
,呋喃基,噻吩基,噁唑基,异噁唑基,噻唑基,异噻唑基,噁
二唑基,噻二唑基,吡啶基,嘧啶基,三嗪基,吡唑基-C1-C4烷
基,呋喃基-C1-C4烷基,噻吩基-C1-C4烷基,噁唑基-C1-C4烷基
,异噁唑基-C1-C4烷基,噻唑基-C1-C4烷基,吡啶基-C1-C4烷
基,嘧啶基-C1-C4烷基,吡唑基甲氧基,呋喃基甲氧基,全氢
化吡喃基甲氧基或吡啶基甲氧基,它们各自均可被硝基、氰基、
羧基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4
卤代烷氧基和/或C1-C4烷氧基羰基可选地取代,R4代表氢、氟、氯、溴或具有1-4个碳原子并可被氟和/或氯可选地
取代的烷基,R5代表氢、氟、氯、溴或具有1-4个碳原子并可被氟和/或氯可选地
取代的烷基,R6代表氢,羟基,氨基或各具有至多4个碳原子并均可被氟、氯或氰
基可选地取代的烷基、烷氧基、链烯基或炔基,和(2)1至3种来自包含下述类型的活性化合物(a)和/或(b)的第2类
除莠剂的活性化合物:
(a)上述的式(II)氨基甲酰基四唑啉酮,其中R7和R8相同或不同,各自互相独立地代表氢;各具有至多6个
碳原子并均可被卤素、氰基或C1-C4烷氧基可选地取代的
烷基,链烯基或炔基;环烷基,环烯基或环烷基烷基,它
们各自在环烷基部分具有3-8个碳原子,在环烯基部分可选
地具有5或6个碳原子,并在烷基部分可选地具有1-4个碳原
子,并且它们各自均可被卤素、氰基、羧基、C1-C4烷基
或C1-C4烷氧基羰基可选地取代;或苯基,萘基,苯基-C1
-C4烷基或萘基-C1-C4烷基,它们各自均可被卤素、氰基、
硝基、羧基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基
或C1-C4卤代烷氧基可选地取代,和R9代表各具有至多6个碳原子并均可被卤素、氰基或C1-C4烷
氧基可选地取代的烷基,链烯基或炔基;环烷基,环烯基
或环烷基烷基,它们各自在环烷基部分具有3-8个碳原子,
在环烯基部分可选地具有5或6个碳原子,并在烷基部分可
选地具有1-4个碳原子,并且它们各自均可被卤素、氰基、
羧基、C1-C4烷基或C1-C4烷氧基羰基可选地取代;苯基,
萘基,苯基-C1-C4烷基或萘基-C1-C4烷基,它们各自均
可被卤素、氰基、硝基、羧基、C1-C4烷基、C1-C4卤代烷
基、C1-C4烷氧基或C1-C4卤代烷氧基可选地取代;或杂
环基或杂环基-C1-C4烷基,它们各自均可被卤素、氰基、
硝基、羧基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基
或C1-C4卤代烷氧基可选地取代,杂环基在各种情况(即使
与烷基结合)下均代表来自下列一组基团的基团:呋喃基,
四氢呋喃基,噻吩基,四氢噻吩基,噁唑基,异噁唑基,
噻唑基,异噻唑基,噁二唑基,噻二唑基,吡啶基,嘧啶
基和三嗪基,(b)来自下列的水稻除莠剂(“通用名”或“代号”):cyclosulfamuron,AKD-741,amiprophos(-methyl),anilofos,benfuresate,bensulfuron (-methyl),地散磷,噻草平,杀草丹(thiobencarb),benzofenap,治草醚,bromobutide,去草安,butamifos,butenachlor,cafenstrole,chlormethoxynil,chlomitrofen,cinmethylin,CL-303569,CL-303578,cinosulfuron,clomeprop,2,4-D,cyhalofop-butyl,dimepiperate,dimethametryn,dithiopyr,azimsulfuron,dymron(dainuron),esprocarb,GS-32911,HOE-404,HOE-30374,HOK-7501,etobenzanid,imazosulfuron,cumyluron,KIH-911(KUH-911),KIH920(KUH920),triazofenamide,KPP-314,MCPA,MCPB,mefenacet,草达灭,NC-310,NC-311,naproanilide,除草醚,thenylchlor,恶草灵,piperophos,pretilachlor,扑草净,敌稗,pyrazolate,pyrazosulfuron(-ethyl),pyrazoxyfen,pyributicarb,quinclorac,西草净,氟乐灵和X-52,其中,在各种情况下,1重量份第1类活性化合物一般配以0.01-100重量份第2类活性化合物。
特别有意义的本发明除莠组合物是含有以下组分的本发明除莠组合物:(I)上述式(I)或(Ia)化合物,其中Q1代表氧或硫,Q2代表氧或硫,R1代表氢、氟、氯或溴,R2代表氟、氯、溴、碘或氰基,R3代表-A1-a2-a3基团,其中,A1代表单键、氧、硫、-SO-、-SO2-、-CO-或基团-N-A4-,其
中A4代表氢、羟基、甲基、乙基、正丙基或异丙基、甲氧基、乙
氧基、正丙氧基或异丙氧基、甲磺酰基或乙磺酰基,或(A1)代
表亚甲基、乙烷-1,1-二基、乙烷-1,2-二基、丙烷-1,1-二
基、丙烷-1,2-二基,丙烷-1,3-二基、乙烯-1,2-二基、
丙烯-1,2-二基、丙烯-1,3-二基、乙炔-1,2-二基、丙炔
-1,2-二基或丙炔-1,3-二基,A2代表单键、氧、硫、-SO-、-SO2-、-CO-或基团-N-A4-,其
中A4代表氢、羟基、甲基、乙基、正丙基或异丙基、甲氧基、乙
氧基、正丙氧基或异丙氧基、甲磺酰基、乙磺酰基、正丙磺酰基
或异丙磺酰基或苯磺酰基,或(A2)代表亚甲基、乙烷-1,1-二
基、乙烷-1,2-二基、丙烷-1,1-二基、丙烷-1,2-二基,丙
烷-1,3-二基、乙烯-1,2-二基、丙烯-1,2-二基、丙烯-1,
3-二基、乙炔-1,2-二基、丙炔-1,2-二基或丙炔-1,3-二
基,A3代表氢,羟基,氨基,氰基,硝基,羧基,氨基甲酰基,磺基,
氟,氯,溴;甲基,乙基,正丙基或异丙基,正、异、仲或叔丁
基,正、异、仲或叔戊基,甲氧基,乙氧基,正或异丙氧基,正
、异、仲或叔丁氧基,正、异、仲或叔戊氧基,甲硫基,乙硫
基,正或异丙硫基,正、异、仲或叔丁硫基,甲基亚磺酰基,乙
基亚磺酰基,正或异丙基亚磺酰基,甲磺酰基,乙磺酰基,正或
异丙磺酰基,甲基氨基,乙基氨基,正或异丙基氨基,正、异、
仲或叔丁基氨基,二甲氨基,二乙氨基,甲氧基羰基,乙氧基羰
基,正或异丙氧基羰基,二甲氧基磷酰基,二乙氧基磷酰基,二
丙氧基磷酰基或二异丙氧基磷酰基,它们各自均可被氟、氯、甲
氧基或乙氧基可选地取代;丙烯基,丁烯基,丙烯氧基,丁烯氧基
,丙烯基氨基,丁烯基氨基,丙叉氨基(propylidenamino),
丁叉氨基,丙烯氧基羰基,丁烯氧基羰基,丙炔基,丁炔基,丙
炔氧基,丁炔氧基,丙炔基氨基,丁炔基氨基,丙炔氧基羰基或
丁炔氧基羰基,它们各自均可被氟或氯可选地取代;环丙基,环
丁基,环戊基,环己基,环丙氧基,环丁氧基,环戊氧基,环己
氧基,环丙基甲基,环丁基甲基,环戊基甲基,环己基甲基,环
丙基甲氧基,环丁基甲氧基,环戊基甲氧基,环己基甲氧基,环
戊叉氨基,环己叉氨基,环戊氧基羰基,环已氧基羰基,环戊基
甲氧基羰基或环己基甲氧基羰基,它们各自均可被氟、氯、氰基
、羧基、甲基、乙基、正丙基或异丙基、甲氧基羰基或乙氧基羰
基可选地取代;或者苯基,苯氧基,苄基,苯基乙基,苄氧基,
苯氧基羰基,苄氧基羰基(在每种情况下均可选地完全或部分氢
化的)吡咯基,吡唑基,咪唑基,三唑基,呋喃基,噻吩基,噁
唑基,异噁唑基,噻唑基,异噻唑基,噁二唑基,噻二唑基,吡
啶基,嘧啶基,三嗪基,吡唑基甲基,呋喃基甲基,噻吩基甲基
,噁唑基甲基,异噁唑基甲基,噻唑基甲基,吡啶基甲基,嘧啶
基甲基,吡唑基甲氧基,呋喃基甲氧基或吡啶基甲氧基,它们各
自均可被下列基团可选地取代:硝基、氰基、羧基、氟、氯、溴
、甲基、乙基、正丙基或异丙基、三氟甲基、甲氧基、乙氧基、
正丙氧基或异丙氧基、二氟甲氧基、三氟甲氧基、甲氧基羰基和
/或乙氧基羰基,R4代表氢、氟、氯,或者代表甲基或乙基,它们各自均可被氟和/或
氯可选地取代,R5代表氢、氟、氯,或者代表甲基或乙基,它们各自均可被氟和/或
氯可选地取代,R6代表氢、羟基、氨基,或者代表甲基、乙基、正丙基或异丙基、甲氧基、乙氧基、正丙氧基或异丙氧基、丙烯基或丙炔基,它们各自
均可被氟、氯或氰基可选地取代,和(2)一种或两种来自包含下述类型的活性化合物(a)和/或(b)
的第2类除莠剂的活性化合物:
(a)上述的式(II)氨基甲酰基四唑啉酮,其中
R7和R8相同或不同,各自互相独立地代表氢;甲基,乙基,
正或异丙基,正、异、仲或叔丁基,丙烯基,丁烯基,戊
烯基,丙炔基,丁炔基或戊炔基,它们各自均可被氟、氯
、溴、氰基、甲氧基或乙氧基可选地取代;环丙基,环丁
基,环戊基,环己基,环戊烯基,环己烯基,环丙基甲基
,环丁基甲基,环戊基甲基,环己基甲基,它们各自均可
被氟、氯、溴、氰基、羧基、甲基、乙基、正或异丙基、
甲氧基羰基或乙氧基羰基可选地取代;或苯基,苄基或苯
基乙基,它们各自均可被下列基团可选地取代:氟,氯,
溴,氰基,硝基,羧基,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,二氟甲氧基或三
氟甲氧基,
R9代表甲基,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,它们各自均可被氟、氯、溴、氰基
、甲氧基或乙氧基可选地取代;环丙基,环丁基,环戊基
,环己基,环戊烯基或环己烯基,环丙基甲基,环丁基甲
基,环戊基甲基或环己基甲基,它们各自均可被氟、氯、
溴、氰基、羧基、甲基、乙基、正或异丙基、甲氧基羰基
或乙氧基羰基可选地取代;苯基,萘基,苄基,苯基乙基
,萘基甲基或萘基乙基,它们各自均可被下列基团可选地取代:氟,氯,溴,氰基,硝基,羧基,甲基,乙基,正
或异丙基,正、异、仲或叔丁基,二氟甲基,三氟甲基,
氯二氟甲基,氟二氯乙基,二氯甲基,三氯甲基,氟乙基
,二氟乙基,三氟乙基,氟丙基,二氟丙基,三氟丙基,
氯乙基,二氯乙基,三氯乙基,甲氧基,乙氧基,正或异
丙氧基,二氟甲氧基,三氟甲氧基,氟乙氧基,二氟乙氧
基,三氟乙氧基或氯乙氧基;或杂环基或杂环基-C1-C4烷
基,杂环基(即使与烷基结合)在各种情况下均代表来自
下列的基团:呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,
噁唑基,异噁唑基,噻唑基,异噻唑基,噁二唑基,噻二
唑基,吡啶基,嘧啶基和三嗪基,它们各自均可被下列基
团可选地取代:氟,氯,溴,氰基,硝基,羧基,甲基,
乙基,正或异丙基,正、异、仲或叔丁基,二氟甲基,三
氟甲基,二氯甲基,三氯甲基,甲氧基,乙氧基,正或异
丙氧基,二氟甲氧基或三氟甲氧基,(b)来自下列的水稻除莠剂(“通用名”或“代号”):cyclosulfamuron,AKD-741,amiprophos(-methyl),anilofos,benfuresate,bensulfuron (-methyl),地散磷,噻草平,杀草丹(thiobencarb),benzofenap,治草醚,bromobutide,去草安,butamifos,butenachlor,cafenstrole,chlormethoxynil,chlornitrofen,cinmethylin,CL-303569,CL-303578,cinosulfuron,clomeprop,2,4-D,cyhalofop-butyl,dimepiperate,dimethametryn,dithiopyr,azimsulfuron,dymron(dairnuron),esprocarb,GS-32911,HOE-404,HOE-30374,HOK-7501,etobenzanid,imazosulfuron,cumyluron,KIH-911(KUH-911),KIH920(KUH920),triazofenamide,KPP-314,MCPA,MCPB,mefenacet,草达灭,NC-310,NC-311,naproanilide,除草醚,thenylchlor,恶草灵,piperophos,pretilachlor,扑草净,敌稗,pyrazolate,pyrazosulfuron(-ethy1),pyrazoxyfen,
ptributicarb,quinclorac,西草净,氟乐灵和X-52,其中,在各种情况下,1重量份第1类活性化合物一般配以0.1-10重量份第2类活性化合物。
用作按照本发明的混合物组分的式(I)化合物的实例列在下面各组中:组1:R3在这种情况下具有例如下列意义:甲磺酰氨基,乙磺酰氨基,正或异丙磺酰氨基,正、异、仲或叔丁磺酰氨基,正戊磺酰氨基,三氟甲磺酰氨基,三氟乙磺酰氨基,氯甲磺酰氨基,氯乙磺酰氨基,氯丙磺酰氨基,环丙磺酰氨基,苯磺酰氨基,对甲苯磺酰氨基,N-甲基-N-甲磺酰基氨基,N-甲基-N-乙磺酰基氨基,N-甲基-N-正丙磺酰基氨基,N-甲基-N-异丙磺酰基氨基,N-甲基-N-正丁磺酰基氨基,N-甲基-N-异丁磺酰基氨基,N-甲基-N-仲丁磺酰基氨基,N-甲基-N-叔丁磺酰基氨基,N-甲基-N-正戊磺酰基氨基,N-甲基-N-三氟甲磺酰基氨基,N-甲基-N-三氟乙磺酰基氨基,N-甲基-N-氯甲磺酰基氨基,N-甲基-N-氯乙磺酰基氨基,N-甲基-N-氯丙磺酰基氨基,N-甲基-N-环丙磺酰基氨基,N-甲基-N-苯磺酰基氨基,N-甲基-N-对甲苯磺酰基氨基,N-乙基-N-甲磺酰基氨基,N-乙基-N-乙磺酰基氨基,N-乙基-N-正丙磺酰基氨基,N-乙基-N-异丙磺酰基氨基,N-乙基-N-正丁磺酰基氨基,N-乙基-N-异丁磺酰基氨基,N-乙基-N-仲丁磺酰基氨基,N-乙基-N-叔丁磺酰基氨基,N-乙基-N-正戊磺酰基氨基,N-乙基-N-三氟甲磺酰基氨基,N-乙基-N-三氟乙磺酰基氨基,N-乙基-N-氯甲磺酰基氨基,N-乙基-N-氯乙磺酰基氨基,N-乙基-N-氯丙磺酰基氨基,N-乙基-N-环丙磺酰基氨基,N-乙基-N-苯磺酰基氨基,N-乙基-N-对甲苯磺酰基氨基,N,N-二(甲磺酰基)氨基,N,N-二(乙磺酰基)氨基,N,N-二(正丙磺酰基)氨基,N,N-二(异丙磺酰基)氨基,N,N-二(正丁磺酰基)氨基,N,N-二(环丙磺酰基)氨基,N,N-二(三氟甲磺酰基)氨基,N-甲磺酰基-N-乙磺酰基氨基,N-甲磺酰基-N-正丙磺酰基氨基,N-甲磺酰基-N-异丙磺酰基氨基,N-甲磺酰基-N-正丁磺酰基氨基,N-乙磺酰基-N-正丙磺酰基氨基,N-甲磺酰基-N-环丙磺酰基氨基,N-甲磺酰基-N-三氟甲磺酰基氨基,N-甲磺酰基-N-三氟乙磺酰基氨基,N-甲磺酰基-N-氯甲磺酰基氨基,N-甲磺酰基-N-氯乙磺酰基氨基,N-甲磺酰基-N-氯丙磺酰基氨基,N-甲磺酰基-N-苯磺酰基氨基和N-甲磺酰基-N-对甲苯磺酰基氨基。组2R3在此种情况下具有例如上面组1中所述的意义。组3R3在此种情况下具有例如上面组1中所述的意义。组4R3在此种情况下具有例如上面组1中所述的意义。组5R3在此种情况下具有例如上面组1中所述的意义。组6R3在此种情况下具有例如上面组1中所述的意义。组7R3在此种情况下具有例如上面组1中所述的意义。组8R3在此种情况下具有例如上面组1中所述的意义。组9R3在此种情况下具有例如上面组1中所述的意义。组10R3在此种情况下具有例如上面组1中所述的意义。组11R3在此种情况下具有例如上面组1中所述的意义。组12R3在此种情况下具有例如上面组1中所述的意义。组13R3在此种情况下具有例如上面组1中所述的意义。组14R3在此种情况下具有例如上面组1中所述的意义。组15R3在此种情况下具有例如上面组1中所述的意义。组16R3在此种情况下具有例如上面组1中所述的意义。组17R3在此种情况下具有例如上面组1中所述的意义。组18R3在此种情况下具有例如上面组1中所述的意义。组19R3在此种情况下具有例如上面组1中所述的意义。组20R3在此种情况下具有例如上面组1中所述的意义。
在上述的本专利申请和本专利说明书中描述了式(I)化合物。
式(II)化合物是已知的和/或可按本身已知的方法(参见EP-A571854,EP-A571885,EP-A572855,EP-A578090,EP-A612735)制备的。
现已令人惊讶地发现,上面定义的式(I)芳基尿嘧啶(或芳基硫尿嘧啶)或相应的式(Ia)异构化合物和在第2类项下所述的活性化合物的活性化合物组合体具有特别强的活性,可用于多种作物尤其是水稻或选择性杂草防治中。
令人惊讶的是,按照本发明的活性化合物组合体的除莠活性显著强于各个活性化合物的作用的总和。
因此存在预料不到的真正的协同作用,而不仅仅是作用的补充。该新的活性化合物组合体在许多作物中但尤其是在水稻中是十分耐受的。在这些作物中,所述新的活性化合物组合体还能扩展到可能难以防治的其它杂草。因而该新的活性化合物组合体是十分有价值的选择性除莠剂,特别是可用于水稻的除莠剂。
可提及的可被本发明活性化合物有效地防治的杂草的实例是:双子叶植物杂草:欧芥属,独行菜属,拉拉藤属,繁缕属,母菊属,青黄菊属,牛膝菊属,藜属,荨麻属,千里光属,苋属,马齿苋属,苍耳属,旋花属,番薯属,蓼属,田菁属,豚草属,茄属,蓟属,飞廉属,苦苣菜属,焊菜属,节节菜属,母草属,野芝麻属,婆婆纳属,苘麻属,刺酸模属,黄花稔属,曼陀罗属,堇菜属,鼬瓣花属,罂粟属,矢车菊属,车轴草层,毛茛属,Taraxum;单子叶植物杂草:稗属,狗尾草属,黍属,马唐属,梯牧草属,早熟禾属,狐茅属,属,臂形草属,毒麦属,雀麦属,燕麦属,莎草属,sorhum,冰草属,狗牙根属,雨久花属,飘拂草属,慈姑属,荸荠属,藨草属,Papalum,鸭嘴草属,尖瓣花属,Dactylocenium,剪股颖属,看麦娘属,Apera。
但按照本发明的活性化合物组合体的用途决不限于这些属,而是还能以相同的方法扩展到其它植物。
如上所述,按照本发明的活性化合物组合体对阔叶杂草和草地杂草具有显著的作用,同时对水稻作物来说,具有良好的耐受性。因此可以特别强调用它们在水稻中作选择性除莠剂的可能性。
按照本发明的活性化合物组合体的协同效果在某些浓度比率时是非常显著的。但在活性化合物组合体中的活性化合物的重量比可在相当宽的范围内变动。1重量份第1类的活性化合物一般配0.001-1000、优选0.01-100、更优选0.1-10重量份第2类的活性化合物。
可将活性化合物转化成常规制剂,例如溶液剂、乳液剂、可湿性粉剂、悬浮剂、粉剂、隔离剂(dusting agent)、糊剂、可溶性粉末、颗粒剂、悬浮液-乳液浓缩物、浸有活性化合物的天然和合成物质和在聚合物中的非常细的胶囊。
这些制剂可按已知方法制备,例如将活性化合物与增量剂即液体溶剂和/或固体载体混合,可选地使用表面活性剂,即乳化剂和/或分散剂和/或成泡沫剂。
在用水作增量剂的情况下,还可以例如使用有机溶剂作助溶剂。适宜作为液体溶剂的主要有芳族化合物例如二甲苯、甲苯或烷基萘类,囟代芳族化合物和卤代脂族烃类,例如氯苯类氯乙烯类或二氯甲烷,脂族烃类,例如环己烷或石蜡类,例如石油馏分,矿物油和植物油,醇类,例如丁醇或乙二醇及其醚和酯,酮类,例如丙酮,甲基·乙基酮,甲基·异丁基酮或环己酮,强极性溶剂,例如二甲基甲酰胺和二甲亚砜,以及水。
适宜作为固体载体的有例如铵盐和粉碎的天然矿物质,例如高岭土,粘土,滑石,白垩,石英,硅镁土,蒙脱石或硅藻土,和粉碎的合成的无机物质,例如高度分散的二氧化硅、三氧化铝和硅酸盐;适宜用作颗粒剂用固体载体的有例如粉碎并分级的天然岩石,例如方解石、大理石、浮石、海泡石和白云石,以及合成的有机和无机粉的颗粒,和有机物质例如锯屑、椰子壳、玉米棒子和烟草茎的颗粒;适宜作为乳化剂和/或成泡沫剂的有例如非离子和阴离子乳化剂,例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;适宜作为分散剂的有例如木素-亚硫酸盐废液和甲基纤维素。
在所述制剂中可以使用粘合剂例如羧甲基纤维素和粉末形式、颗粒形式或胶乳状天然的或合成的聚合物,例如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯脂以及天然的磷脂类,例如脑磷脂和卵磷脂,和合成的磷脂类。基它的添加剂可以是矿物油和植物油。
可以使用着色剂例如无机颜料,例如氧化铁,氧化钛和普鲁士蓝,和有机染料,例如茜素染料,偶氮染料和金属酞菁染料,和微量营养物例如镁、锰、硼、铜、钴、钼和锌的盐。
所述制剂一般含0.1-95%(重量)活性化合物,优选含0.5-90%(重量)活性化合物。
按照本发明的活性化合物组合体一般以成品制剂的形式应用。但还可以将含在活性化合物组合体中的活性化合物在施用期间混合在各个制剂中,即以桶混制剂(tank mix)的形式来施用。
所述新的活性化合物组合体可直接或以其制剂形式用于杂草防治,并且还可以与其它已知的水稻除莠剂的混合物形式成品制剂或桶混制剂的形式用于杂草防治。还可以是与其它已知活性化合物例如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、生长促进剂、植物营养物和改善土壤结构的试剂的混合物。此外对于某些应用目的,特别是出苗后应用,在所述制剂中吸收植物可耐受的矿物油或植物油(例如可商购得的“Oleo Dupont 11E”)或铵盐例如硫酸铵或硫氰酸铵作另外的添加剂可能是有利的。
按照本发明的活性化合物组合体可以其本身、其制剂形式或通过由其进一步稀释而制得的使用形式例如即可使用的溶液、悬浮液、乳剂、粉剂、糊剂和颗粒剂形式来使用。它们以常规方法例如通过洒水、喷雾、雾化或撒播来使用。
按照本发明的活性化合物组合体可在植物出苗前或出苗后施用。可在播种前将它们掺入土壤中。
按照本发明的活性化合物组合体的施用比率可在相当大的范围内变动。这主要取决于所需作用的性质。一般来讲,施用比率为每公顷土壤表面10g至10kg活性化合物组合体,优选每公顷50g至5kg,特别是每公顷100g至2kg。
尽管单个活性化合物显示弱的除莠作用,但按照本发明的组合体却无一例外地显示出非常好且广泛有效地防治主要出现在水稻中的杂草的作用,这超出了纯粹加和的作用。
若活性化合物组合体的除莠作用大于所用的各个活性化合物的除莠作用,则总是给除莠剂带来协同效果。
对于给定的两种除莠剂的组合体的预计的作用可如下计算(参见Colby,S.R;"Calculating synergistic and antagonisticresponses of herbicide combinations",Weeds 15,第20-22页,1967):若X=% 被施用比率为pkg/公顷的除莠剂A
(第1类活性化合物)损害,和Y=% 被施用比率为qkg/公顷的除莠剂B
(第2类活性化合物)损害,和E= 被施用比率为p和q kg/公顷的除莠剂A和B预计的损害,则 E=X+Y-(X*Y/100)。
若实际的损害大于计算的损害,则该组合体在其作用方面是超加性的,即显示协同效果。
从按照本发明的活性化合物组合体的施用试验可以得出:按照本发明的活性化合物组合体的除莠作用大于计算的除莠作用,即该新的活性化合物组合体起协同作用。
Claims (8)
1.除莠组合物,其特征在于含有有效量的活性化合物组合体,该组合体包括(1)通式(I)芳基尿嘧啶或芳基硫尿嘧啶或其异构化合物——通式(Ia)芳基尿嘧啶或芳基硫尿嘧啶在式(I)和(Ia)中,Q1代表氧或硫,Q2代表氧或硫,R1代表氢或卤素,R2代表囟素或氰基,R3代表-A1-A2-A3基团,其中A1代表单键、氧、硫、-SO-、-SO2-、-CO-或基团-N-A4-
,其中A4代表氢、羟基、烷基、烷氧基、芳基、烷基磺酰基或
芳基磺酰基,或(A1)代表烷二基、链烯二基、氮杂链烯二基、
炔二基、环烷二基、环烯二基或亚芳基,它们各自均可被可选
地取代,A2代表单键、氧、硫、-SO-、-SO2-、-CO-或基团-N-A4-
,其中A4代表氢、烷基、芳基、烷基羰基、烷基磺酰基或芳基
磺酰基,或(A2)代表烷三基、链烯二基、氮杂链烯二基、炔
二基、环烷二基、环烯二基或亚芳基,它们各自均可被可选地
取代,A3代表氢、羟基、巯基、氨基、氰基、异氰基、氰硫基、硝基、
羧基、氨基甲酰基、硫代氨基甲酰基、磺基、氯磺酰基、卤素
,或烷基、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、烷氧基羰基、二烷氧(硫)基磷酰基、
链烯基、链烯氧基、链烯基氨基、烷叉氨基、链烯氧基羰基、
炔基、炔氧基、炔基氨基、炔氧基羰基、环烷基、环烷氧基、
环烷基烷基、环烷基烷氧基、环烷叉氨基、环烷氧羰基、环烷
基烷氧基羰基、芳基、芳氧基、芳基烷基、芳基烷氧基、芳氧
基羰基、芳基烷氧基羰基、杂环基、杂环基烷基、杂环基烷氧
基或杂环基烷氧基羰基,它们各自均可被可选地取代,R4代表氢、卤素或可选地被取代的烷基,R5代表氢、卤素或可选地被取代的烷基,和R6代表氢、羟基、氨基,或烷基、烷氧基、链烯基或炔基,它们各
自均可被可选地取代,
(“第1类活性化合物”)和(2)一种或多种来自第2类除莠剂的除莠活性化合物(“第2类活性化合物”),包含下述类型的活性化合物(a)和/或(b):(a)通式(II)氨基甲酰基四唑啉酮式中R7和R8相同或不同,各自互相独立地代表氢或来自下列的一组
基团的基团:烷基、链烯基、炔基、环烷基、环烯基、环烷
基烷基、芳基和芳基烷基,这些基团各自均可被可选地取代,
和R9代表来自下列的一组基团的基团:烷基、链烯基、炔基、环
烷基、环烯基、环烷基烷基、芳基、芳基烷基、杂环基和杂
环基烷基,它们各自均可被可选地取代,(b)来自下列的水稻除莠剂(“通用名”或“代号”):cyclosulfamuron,AKD-741,amiprophos(-methyl),anilofos,benfuresate,bensulfuron(-methyl),地散磷,噻草平,杀草丹(thiobencarb),benzofenap,治草醚,bromobutide,去草安,butamifos,butenachlor,catenstrole,chlormethoxynil,chlomitrofen,cinmethylin,CL-303569,CL-303578,cinosulfuron,clomeprop,2,4-D,cyhalofop-butyl,dimepiperate,dinethametryn,dithiopyr,azimsulfuron,dymron(daimuron),esprocarb,GS-32911,HOE-404,HOE-30374,HOK-7501,etobenzanid,imazosulfuron,cumyluron,KIH-911(KUH-911),KIH920(KUH920),triazofenamide,KPP-314,MCPA,MCPB,mefenacet,草达灭,NC-310,NC-311,naproanilide,除草醚,thenylchlor,恶草灵,piperophos,pretilachlor,扑草净,敌稗,pyrazolate,pyrazosulfuron(-ethyl),pyrazoxyfen,pyributicarb,quinclorac,西草净,氟乐灵和X-52。
2.按照权利要求1的除莠组合物,其特征在于含有活性化合物组合体,该组合体包括(1)按照权利要求1的式(I)或(Ia)化合物,其中Q1代表氧或硫,Q2代表氧或硫,R1代表氢、氟、氯或溴,R2代表氟、氯、溴、碘或氰基,R3代表-A1-A2-A3基团,其中,A1代表单键、氧、硫、-SO-、-SO2-、-CO-或基团-N-A4-,其
中A4代表氢、羟基、C1-C4烷基、C1-C4烷氧基、苯基、C1-C4
烷基磺酰基或苯基磺酰基,或(A1)代表C1-C6烷二基、C2-C6
链烯二基、C2-C6氮杂链烯二基、C2-C6炔二基、C3-C6环烷二
基、C3-C6环烯二基或亚苯基,它们各自均可被氟、氯或溴可选
地取代,A2代表单键、氧、硫、-SO-、-SO2-、-CO-或基团-N-A4-,其
中A4代表氢、羟基、C1-C4烷基、C1-C4烷氧基、苯基、C1-C4
烷基磺酰基或苯基磺酰基,或(A2)代表C1-C6烷二基、C2-C6
链烯二基、C2-C6氮杂链烯二基、C2-C6炔二基、C3-C6环烷二
基、C3-C6环烯二基或亚苯基,它们各自均可被氟、氯或溴可选
地取代,A3代表氢,羟基,氨基,氰基,异氰基,氰硫基,硝基,羧基,氨
基甲酰基,硫代氨基甲酰基,磺基,氯磺酰基,卤素;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,烷氧基羰基或二烷氧(硫)基磷酰基,它们在烷基部分各
具有1-6个碳原子,并均可被囟素或C1-C4烷氧基可选地取代;
链烯基,链烯氧基,链烯基氨基,烷叉氨基,链烯氧基羰基,炔
基,炔氧基,炔基氨基或炔氧基羰基,它们在所述链烯基、烷叉
或炔基部分各具有2-6个碳原子,并均可被卤素可选地取代;环
烷基,环烷氧基,环烷基烷基,环烷基烷氧基,环烷叉氨基,环
烷氧基羰基或环烷基烷氧基羰基,它们在所述环烷基部分各具有
3-6个碳原子并可选地在所述烷基部分具有1-4个碳原子,并均可
被卤素、氰基、羧基、C1-C4烷基和/或C1-C4烷氧基羰基可选
地取代;或苯基,苯氧基,苯基-C1-C4烷基,苯基-C1-C4烷
氧基,苯氧基羰基或苯基-C1-C4烷氧基羰基,(在每种情况下
均可选地完全或部分氢化的)吡咯基,吡唑基,咪唑基,三唑基
,呋喃基,噻吩基,噁唑基,异噁唑基,噻唑基,异噻唑基,噁
二唑基,噻二唑基,吡啶基,嘧啶基,三嗪基,吡唑基-C1-C4烷
基,呋喃基-C1-C4烷基,噻吩基-C1-C4烷基,噁唑基-C1-C4烷基
,异噁唑基-C1-C4烷基,噻唑基-C1-C4烷基,吡啶基-C1-C4烷
基,嘧啶基-C1-C4烷基,吡唑基甲氧基,呋喃基甲氧基,全氢
化吡喃基甲氧基或吡啶基甲氧基,它们各自均可被硝基、氰基、
羧基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4
卤代烷氧基和/或C1-C4烷氧基羰基可选地取代,R4代表氢、氟、氯、溴或具有1-4个碳原子并可被氟和/或氯可选地
取代的烷基,R5代表氢、氟、氯、溴或具有1-4个碳原子并可被氟和/或氯可选地
取代的烷基,R6代表氢,羟基,氨基或各具有至多4个碳原子并均可被氟、氯或氰
基可选地取代的烷基、烷氧基、链烯基或炔基,和(2)1至3种来自包含下述类型的活性化合物(a)和/或(b)的第
2类除莠剂的活性化合物:(a)按照权利要求1的式(II)氨基甲酰基四唑啉酮,其中R7和R8相同或不同,各自互相独立地代表氢;各具有至多6个
碳原子并均可被卤素、氰基或C1-C4烷氧基可选地取代的
烷基,链烯基或炔基;环烷基,环烯基或环烷基烷基,它
们各自在环烷基部分具有3-8个碳原子,在环烯基部分可选
地具有5或6个碳原子,并在烷基部分可选地具有1-4个碳原
子,并且它们各自均可被囟素、氰基、羧基、C1-C4烷基
或C1-C4烷氧基羰基可选地取代;或苯基,萘基,苯基-C1
-C4烷基或萘基-C1-C4烷基,它们各自均可被卤素、氰基、
硝基、羧基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基
或C1-C4卤代烷氧基可选地取代,和R9代表各具有至多6个碳原子并均可被卤素、氰基或C1-C4烷
氧基可选地取代的烷基,链烯基或炔基;环烷基,环烯基
或环烷基烷基,它们各自在环烷基部分具有3-8个碳原子,
在环烯基部分可选地具有5或6个碳原子,并在烷基部分可
选地具有1-4个碳原子,并且它们各自均可被卤素、氰基、
羧基、C1-C4烷基或C1-C4烷氧基羰基可选地取代;苯基
,萘基,苯基-C1-C4烷基或萘基-C1-C4烷基,它们各自均
可被卤素、氰基、硝基、羧基、C1-C4烷基、C1-C4卤代烷
基、C1-C4烷氧基或C1-C4卤代烷氧基可选地取代;或杂
环基或杂环基-C1-C4烷基,它们各自均可被卤素、氰基、
硝基、羧基、C1-C4烷基、C1-C4囟代烷基、C1-C4烷氧基
或C1-C4卤代烷氧基可选地取代,杂环基在各种情况(即使
与烷基结合)下均代表来自下列一组基团的基团:呋喃基,
四氢呋喃基,噻吩基,四氢噻吩基,噁唑基,异噁唑基,
噻唑基,异噻唑基,噁二唑基,噻二唑基,吡啶基,嘧啶
基和三嗪基,(b)来自下列的水稻除莠剂(“通用名”或“代号”):cyclosulfamuron,AKD-741,amiprophos(-methyl),anilofos,benfuresate,bensulfuron (-methyl),地散磷,噻草平,杀草丹(thiobencarb),benzofenap,治草醚,bromobutide,去草安,butamifos,butenachlor,cafenstrole,chlormethoxynil,chlomitrofen,cinmethylin CL-303569,CL-303578,cinosulfuron,clomeprop,2,4-D,cyhalofop-butyl,dimepiperate,dimethametryn,dithiopyr,azimsulfuron,dymron(daimuron),esprocarb,GS-32911,HOE-404,HOE-30374,HOK-7501,etobenzanid,imazosulfuron,cumyluron,KIH-911(KUH-911),KIH920(KUH920),triazofenamide,KPP-314,MCPA,MCPB,mefenacet,草达灭,NC-310,NC-311,naproanilide,除草醚,thenylchlor,恶草灵,piperophos,pretilachlor,扑草净,敌稗,pyrazolate,pyrazosulfuron (-ethyl),pyrazoxyfen,pyributicarb,quinclorac,西草净,氟乐灵和X-52。
3.按照权利要求1的除莠组合物,其特征在于含有活性化合物组合体,该组合体包括(1)按照权利要求1的式(I)或(Ia)化合物,其中Q1代表氧或硫,Q2代表氧或硫,R1代表氢、氟、氯或溴,R2代表氟、氯、溴、碘或氰基,R3代表-A1-A2-A3基团,其中,
A1代表单键、氧、硫、-SO-、-SO2-、-CO-或基团-N-A4-,其
中A4代表氢、羟基、甲基、乙基、正丙基或异丙基、甲氧基、乙
氧基、正丙氧基或异丙氧基、甲磺酰基或乙磺酰基,或(A1)代
表亚甲基、乙烷-1,1-二基、乙烷-1,2-二基、丙烷-1,1-二
基、丙烷-1,2-二基,丙烷-1,3-二基、乙烯-1,2-二基、
丙烯-1,2-二基、丙烯-1,3-二基、乙炔-1,2-二基、丙炔
-1,2-二基或丙炔-1,3-二基,A2代表单键、氧、硫、-SO-、-SO2-、-CO-或基团-N-A4-,其
中A4代表氢、羟基、甲基、乙基、正丙基或异丙基、甲氧基、乙
氧基、正丙氧基或异丙氧基、甲磺酰基、乙磺酰基、正丙磺酰基
或异丙磺酰基或苯磺酰基,或(A2)代表亚甲基、乙烷-1,1-二
基、乙烷-1,2-二基、丙烷-1,1-二基、丙烷-1,2-二基,丙
烷-1,3-二基、乙烯-1,2-二基、丙烯-1,2-二基、丙烯-1,
3-二基、乙炔-1,2-二基、丙炔-1,2-二基或丙炔-1,3-二
基,A3代表氢,羟基,氨基,氰基,硝基,羧基,氨基甲酰基,磺基,
氟,氯,溴;甲基,乙基,正丙基或异丙基,正、异、仲或叔丁
基,正、异、仲或叔戊基,甲氧基,乙氧基,正或异丙氧基,正
、异、仲或叔丁氧基,正、异、仲或叔戊氧基,甲硫基,乙硫
基,正或异丙硫基,正、异、仲或叔丁硫基,甲基亚磺酰基,乙
基亚磺酰基,正或异丙基亚磺酰基,甲磺酰基,乙磺酰基,正或
异丙磺酰基,甲基氨基,乙基氨基,正或异丙基氨基,正、异、
仲或叔丁基氨基,二甲氨基,二乙氨基,甲氧基羰基,乙氧基羰
基,正或异丙氧基羰基,二甲氧基磷酰基,二乙氧基磷酰基,二
丙氧基磷酰基或二异丙氧基磷酰基,它们各自均可被氟、氯、甲
氧基或乙氧基可选地取代;丙烯基,丁烯基,丙烯氧基,丁烯氧
基,丙烯基氨基,丁烯基氨基,丙叉氨基,丁叉氨基,丙烯氧基
羰基,丁烯氧基羰基,丙炔基,丁炔基,丙炔氧基,丁炔氧基,
丙炔基氨基,丁炔基氨基,丙炔氧基羰基或丁炔氧基羰基,它们
各自均可被氟或氯可选地取代;环丙基,环丁基,环戊基,环己
基,环丙氧基,环丁氧基,环戊氧基,环己氧基,环丙基甲基,
环丁基甲基,环戊基甲基,环己基甲基,环丙基甲氧基,环丁基
甲氧基,环戊基甲氧基,环己基甲氧基,环戊叉氨基,环己叉氨
基,环戊氧基羰基,环己氧基羰基,环戊基甲氧基羰基或环己基
甲氧基羰基,它们各自均可被氟、氯、氰基、羧基、甲基、乙基
、正丙基或异丙基、甲氧基羰基或乙氧基羰基可选地取代;或者
苯基,苯氧基,苄基,苯基乙基,苄氧基,苯氧基羰基,苄氧基
羰基(在每种情况下均可选地完全或部分氢化的)吡咯基,吡唑
基,咪唑基,三唑基,呋喃基,噻吩基,噁唑基,异噁唑基,噻
唑基,异噻唑基,噁二唑基,噻二唑基,吡啶基,嘧啶基,三嗪
基,吡唑基甲基,呋喃基甲基,噻吩基甲基,噁唑基甲基,异噁
唑基甲基,噻唑基甲基,吡啶基甲基,嘧啶基甲基,吡唑基甲氧
基,呋喃基甲氧基或吡啶基甲氧基,它们各自均可被下列基团可
选地取代:硝基、氰基、羧基、氟、氯、溴、甲基、乙基、正丙
基或异丙基、三氟甲基、甲氧基、乙氧基、正丙氧基或异丙氧基
、二氟甲氧基、三氟甲氧基、甲氧基羰基和/或乙氧基羰基,R4代表氢、氟、氯,或者代表甲基或乙基,它们各自均可被氟和/或
氯可选地取代,R5代表氢、氟、氯,或者代表甲基或乙基,它们各自均可被氟和/或
氯可选地取代,R6代表氢、羟基、氨基,或者代表甲基、乙基、正丙基或异丙基、甲
氧基、乙氧基、正丙氧基或异丙氧基、丙烯基或丙炔基,它们各自
均可被氟、氯或氰基可选地取代,和(2)一种或两种来自包含下述类型的活性化合物(a)和/或(b)
的第2类除莠剂的活性化合物:(a)按照权利要求1的式(II)氨基甲酰基四唑啉酮,其中
R7和R8相同或不同,各自互相独立地代表氢;甲基,乙基,
正或异丙基,正、异、仲或叔丁基,丙烯基,丁烯基,戊
烯基,丙炔基,丁炔基或戊炔基,它们各自均可被氟、氯
、溴、氰基、甲氧基或乙氧基可选地取代;环丙基,环丁
基,环戊基,环己基,环戊烯基,环己烯基,环丙基甲基
,环丁基甲基,环戊基甲基,环己基甲基,它们各自均可
被氟、氯、溴、氰基、羧基、甲基、乙基、正或异丙基、
甲氧基羰基或乙氧基羰基可选地取代;或苯基,苄基或苯
基乙基,它们各自均可被下列基团可选地取代:氟,氯,
溴,氰基,硝基,羧基,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,二氟甲氧基或三
氟甲氧基,R9代表甲基,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,它们各自均可被氟、氯、溴、氰基
、甲氧基或乙氧基可选地取代;环丙基,环丁基,环戊基
,环己基,环戊烯基或环己烯基,环丙基甲基,环丁基甲
基,环戊基甲基或环己基甲基,它们各自均可被氟、氯、
溴、氰基、羧基、甲基、乙基、正或异丙基、甲氧基羰基
或乙氧基羰基可选地取代;苯基,萘基,苄基,苯基乙基
,萘基甲基或萘基乙基,它们各自均可被下列基团可选地
取代:氟,氯,溴,氰基,硝基,羧基,甲基,乙基,正
或异丙基,正、异、仲或叔丁基,二氟甲基,三氟甲基,
氯二氟甲基,氟二氯乙基,二氯甲基,三氯甲基,氟乙基
,二氟乙基,三氟乙基,氟丙基,二氟丙基,三氟丙基,
氯乙基,二氯乙基,三氯乙基,甲氧基,乙氧基,正或异
丙氧基,二氟甲氧基,三氟甲氧基,氟乙氧基,二氟乙氧
基,三氟乙氧基或氯乙氧基;或杂环基或杂环基-C1-C4烷
基,杂环基(即使与烷基结合)在各种情况下均代表来自
下列的基团:呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,
噁唑基,异噁唑基,噻唑基,异噻唑基,噁二唑基,噻二
唑基,吡啶基,嘧啶基和三嗪基,它们各自均可被下列基
团可选地取代:氟,氯,溴,氰基,硝基,羧基,甲基,
乙基,正或异丙基,正、异、仲或叔丁基,二氟甲基,三
氟甲基,二氯甲基,三氯甲基,甲氧基,乙氧基,正或异
丙氧基,二氟甲氧基或三氟甲氧基,(b)来自下列的水稻除莠剂(“通用名”或“代号”):cyclosulfamuron,AKD-741,amiprophos (-methyl),anilofos,benfuresate,bensulfuron(-methyl),地散磷,噻草平,杀草丹(thiobencarb),benzofenap,治草醚,bromobutide,去草安,butamifos,butenachlor,catenstrole,chlormethoxynil,chlornitrofen,cinmethylin,CL-303569,CL-303578,cinosulfuron,clomeprop,2,4-D,cyhalofop-butyl,dimepiperate,dimethametryn,dithiopyr,azimsulfuron,dymron(daimuron),esprocarb,GS-32911,HOE-404,HOE-30374,HOK-7501,etobenzanid,imazosulfuron,cumyluron,KIH-911(KUH-911),H920(KUH920),triazofenamide,KPP-314,MCPA,MCPB,mefenacet,草达灭,NC-310,NC-311,naproanilide,除草醚,thenylchlor,恶草灵,piperophos,pretilachlor,扑草净,敌稗,pyrazolate,pyrazosulfuron(-ethyl),pyrazoxyfenpyributicarb,quinclorac,西草净,氟乐灵和X-52。
4.按照权利要求1的除莠组合物,其特征在于:在该活性化合物组合体中,按照权利要求1的通式(I)芳基尿嘧啶或芳基硫尿嘧啶或其异构化合物——按照权利要求1的通式(Ia)化合物与来自包含权利要求1中所述的活性化合物(a)和/或(b)类的除莠剂的这类除莠活性化合物之重量比在1∶0.001和1∶1000之间。
5.杂草防治方法,其特征在于使按照权利要求1至4的活性化合物组合体作用于杂草和/或其生境。
6.按照权利要求1至4的活性化合物组合体在防治杂草方面的用途。
7.除莠组合物的制备方法,其特征在于:将按照权利要求1至4的活性化合物组合体与增量剂和/或表面活性剂混合。
8.按照权利要求7的制备除莠组合物的方法,其特征在于该制剂含0.1至95%(重量)之间的活性化合物。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4437197A DE4437197A1 (de) | 1994-10-18 | 1994-10-18 | Herbizide auf Basis von Aryluracilen zur Verwendung im Reisanbau |
DEP4437197.7 | 1994-10-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1129517A true CN1129517A (zh) | 1996-08-28 |
Family
ID=6531063
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN95116184A Pending CN1129517A (zh) | 1994-10-18 | 1995-10-18 | 基于芳基尿嘧啶类的用于水稻栽培中的除莠剂 |
Country Status (5)
Country | Link |
---|---|
JP (1) | JPH08208412A (zh) |
KR (1) | KR960013201A (zh) |
CN (1) | CN1129517A (zh) |
BR (1) | BR9504450A (zh) |
DE (1) | DE4437197A1 (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1092486C (zh) * | 1996-03-15 | 2002-10-16 | 诺瓦提斯公司 | 除草组合物以及防治杂草的方法 |
CN1306873C (zh) * | 1997-01-21 | 2007-03-28 | 拜尔公司 | 基于1-(2-氯苯基)-4-(n-环己基-n-乙基氨基羰基)-1,4-二氢-5h-四唑-5-酮和敌稗的选择性除莠剂 |
CN108294006A (zh) * | 2018-03-29 | 2018-07-20 | 佛山市普尔玛农化有限公司 | 一种含有苯嘧磺草胺和四唑酰草胺的除草剂 |
Families Citing this family (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ZA971253B (en) * | 1996-02-16 | 1998-08-14 | Basf Ag | Substituted aromatic phosphonic acid derivatives |
DE19605766A1 (de) * | 1996-02-16 | 1997-08-21 | Basf Ag | Substituierte 2-Phenylpyridine |
WO1997042188A1 (fr) * | 1996-05-08 | 1997-11-13 | Kumiai Chemical Industry Co., Ltd. | Derives d'uracile a substitution indolyle et herbicides contenant ces derives en tant qu'ingredients actifs |
DE19936438A1 (de) * | 1999-08-03 | 2001-02-08 | Aventis Cropscience Gmbh | Kombinationen von Herbiziden und Safenern |
DE19958381A1 (de) | 1999-12-03 | 2001-06-07 | Bayer Ag | Herbizide auf Basis von N-Aryl-uracilen |
PL215418B1 (pl) | 2000-05-04 | 2013-12-31 | Basf Ag | Podstawione fenylosulfamoilokarboksyamidy, srodek chwastobójczy, srodek do desykacji i/lub defoliacji roslin, zastosowanie podstawionych fenylosulfamoilokarboksyamidów do wytwarzania srodka chwastobójczego/srodka do desykacji i/lub defoliacji roslin i sposób wytwarzania podstawionych fenylosulfamoilokarboksyamidów |
HU228904B1 (hu) * | 2001-09-14 | 2013-06-28 | Basf Ag | 3-Fenil-uracil-alapú herbicid keverékek |
DE10223914A1 (de) * | 2002-05-29 | 2003-12-11 | Bayer Cropscience Ag | Substituierte Phenyluracile |
JP4699358B2 (ja) | 2003-04-08 | 2011-06-08 | ビーエーエスエフ ソシエタス・ヨーロピア | 除草剤又は乾燥性及び/若しくは落葉性化合物としてのベンゼンスルホンアミド誘導体 |
EP3159331A1 (en) | 2010-05-05 | 2017-04-26 | Infinity Pharmaceuticals, Inc. | Tetrazolones as inhibitors of fatty acid synthase |
US11274083B2 (en) | 2017-12-19 | 2022-03-15 | Syngenta Crop Protection Ag | Substituted thiophenyl uracils, salts thereof and the use thereof as herbicidal agents |
WO2019121547A1 (de) | 2017-12-19 | 2019-06-27 | Bayer Aktiengesellschaft | Substituierte thiophenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2019121544A1 (de) | 2017-12-19 | 2019-06-27 | Bayer Aktiengesellschaft | Substituierte thiophenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2021013800A1 (de) | 2019-07-22 | 2021-01-28 | Bayer Aktiengesellschaft | Substituierte n-phenyl-n-aminouracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
US20220289708A1 (en) | 2019-07-22 | 2022-09-15 | Bayer Aktiengesellschaft | Substituted n-phenyl uracils, salts thereof and their use as herbicidal agents |
EP4038054A1 (en) | 2019-10-01 | 2022-08-10 | Bayer Aktiengesellschaft | Pyrimidinedione derivatives |
JP2023539226A (ja) | 2020-08-24 | 2023-09-13 | バイエル、アクチエンゲゼルシャフト | 置換n-フェニルウラシルおよびその塩、ならびに除草活性物質としてのその使用 |
EP4230620A1 (de) | 2022-02-22 | 2023-08-23 | Bayer Aktiengesellschaft | Substituierte n-amino-n´-benzoesäureuracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2023161172A1 (de) | 2022-02-22 | 2023-08-31 | Bayer Aktiengesellschaft | Substituierte n-benzoesäureuracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
EP4230621A1 (de) | 2022-02-22 | 2023-08-23 | Bayer AG | Substituierte n-benzoesäureuracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2024078906A1 (de) | 2022-10-10 | 2024-04-18 | Bayer Aktiengesellschaft | Substituierte n-phenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2024104956A1 (de) | 2022-11-16 | 2024-05-23 | Bayer Aktiengesellschaft | Substituierte cycloalkylsulfanylphenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2024104952A1 (de) | 2022-11-16 | 2024-05-23 | Bayer Aktiengesellschaft | Substituierte cyclopropyloxyphenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2024104954A1 (de) | 2022-11-16 | 2024-05-23 | Bayer Aktiengesellschaft | Substituierte cycloalkyloxyphenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
-
1994
- 1994-10-18 DE DE4437197A patent/DE4437197A1/de not_active Withdrawn
-
1995
- 1995-10-13 JP JP7290574A patent/JPH08208412A/ja active Pending
- 1995-10-13 KR KR1019950035396A patent/KR960013201A/ko not_active Application Discontinuation
- 1995-10-18 BR BR9504450A patent/BR9504450A/pt not_active IP Right Cessation
- 1995-10-18 CN CN95116184A patent/CN1129517A/zh active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1092486C (zh) * | 1996-03-15 | 2002-10-16 | 诺瓦提斯公司 | 除草组合物以及防治杂草的方法 |
CN1306873C (zh) * | 1997-01-21 | 2007-03-28 | 拜尔公司 | 基于1-(2-氯苯基)-4-(n-环己基-n-乙基氨基羰基)-1,4-二氢-5h-四唑-5-酮和敌稗的选择性除莠剂 |
CN108294006A (zh) * | 2018-03-29 | 2018-07-20 | 佛山市普尔玛农化有限公司 | 一种含有苯嘧磺草胺和四唑酰草胺的除草剂 |
Also Published As
Publication number | Publication date |
---|---|
KR960013201A (ko) | 1996-05-22 |
BR9504450A (pt) | 1997-05-20 |
DE4437197A1 (de) | 1996-04-25 |
JPH08208412A (ja) | 1996-08-13 |
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