MXPA97002552A - Selective herbicides based decarbamoiltriazolinonas and deheteroariloxiacetami - Google Patents
Selective herbicides based decarbamoiltriazolinonas and deheteroariloxiacetamiInfo
- Publication number
- MXPA97002552A MXPA97002552A MXPA/A/1997/002552A MX9702552A MXPA97002552A MX PA97002552 A MXPA97002552 A MX PA97002552A MX 9702552 A MX9702552 A MX 9702552A MX PA97002552 A MXPA97002552 A MX PA97002552A
- Authority
- MX
- Mexico
- Prior art keywords
- carbon atoms
- alkyl
- cyano
- substituted
- ethyl
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title claims description 20
- -1 1,1-dimethyl-ethyl-amino carbonyl Chemical group 0.000 claims abstract description 116
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 79
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
- 229910052801 chlorine Inorganic materials 0.000 claims description 24
- 239000000460 chlorine Chemical group 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 24
- 239000011737 fluorine Substances 0.000 claims description 24
- 241000196324 Embryophyta Species 0.000 claims description 22
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000000304 alkynyl group Chemical group 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 12
- HMNRTPKCBIBLHD-UHFFFAOYSA-N 5-oxo-4h-triazole-1-carboxamide Chemical compound NC(=O)N1N=NCC1=O HMNRTPKCBIBLHD-UHFFFAOYSA-N 0.000 claims description 11
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 8
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 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 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 claims description 4
- 125000005108 alkenylthio group Chemical group 0.000 claims description 4
- 125000005109 alkynylthio group Chemical group 0.000 claims description 4
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 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
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
- 125000006038 hexenyl group Chemical group 0.000 claims description 2
- 125000005980 hexynyl group Chemical group 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
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- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 2
- 125000005981 pentynyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000000286 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
- 125000004344 phenylpropyl group Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 8
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 2
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 125000006320 propynyl amino group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 19
- 230000002363 herbicidal effect Effects 0.000 abstract description 12
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 abstract description 6
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Abstract
The present invention relates to a herbicidal composition, characterized in that it comprises a combination of compounds containing: 1) 4-amino-5- (1-methyl-ethyl) -2- (1,1-dimethyl-ethyl-amino carbonyl) -2-4-dihydro-3-H-1,2,4-triazol-3-one as compound I-1, and Ni-propyl-N- (4-fluoro-phenyl) -alpha- (5-trifluoromet il- 1,3,4-thiadiazol-2-yl-oxy) acetamide as compound II-1, wherein 0.001 to 1000 parts by weight of compound II-1 are being used in relation to 1 part by weight of compound I
Description
SELECTIVE HERBICIDES BASED ON CARBAMOILTRIAZOLINOMAS AND HETEROARYLIOXYACETAMIDES
FIELD OF THE INVENTION The invention relates to new synergistic combinations of active ingredients, herbicides, which are constituted by known carbamoyltriazolinones, on the one hand, and known per-heteraarilaxyacetamides, on the other hand and which can be used with a particularly good success for the selective struggle contributed to the weeds in various crops of useful plants. BACKGROUND OF THE INVENTION Carbamoyltriazolinones already constitute, as known herbicides, the subject of a series of patent applications (see EP-A 294666, EP-A 370293, EP-A 391187, EP-A 398096, EP-A 399294, EP-A 415196, EP-A 477646). The known carbamoyltriazolinones have, however, a series of failures in their activity, especially against monocotyledonous weeds. Heteroaryloxyacetamides also constitute, as active herbicides against monocotyledonous weeds, the subject of a series of patent applications (see EP-A 5501, EP-A 18497, EP-A 29171, EP-A 94514, EP-A 100044, EP-A 100045, EP-A 161602, EP-A 195237, EP-A 348734, EP-A 348737). The known heteroaryloxyacetamides are not active, however, in the same way against all monocotyledonous weeds. Surprisingly it has now been found that a number of herbicidal active compounds, known from the group
RFF: 2 ^ 338 formed by the carbamoyltriazolinones in conjunction with known herbicidal active compounds from the group consisting of the heteroaryloxyacetamides, show an excellent synergistic effect with respect to the effect against weeds and which can be used with particular preference mode of combined preparations of broad activity for the selective fight against both the mopacatiledópeas weeds and against the dicotyledonous, in the pre-bud and past-shoot processes, in crops of mopo-cotyledonous and dicotyledonous useful plants, such as, for example, corn and soybeans. DESCRIPTION OF THE INVENTION The object of the invention are synergistic herbicidal agents, characterized in that they have an active content of a combination of active compounds constituted by (1) a carbamoyltriazolinone of the general formula (I)
wherein R 1 signifies hydrogen, hydroxy, amino or means, respectively substituted, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylamino, alkenylamino, alkynylamino, alkylideneamino, dialkylamino, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl R 2 means, where appropriate substituted, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylamino, alkenylamino, alkynylamino, dialkylamino, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, arylc, aryloxy, arylthio, arylamino or arylalkyl and R3 means, optionally substituted, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, arylalkyl, arylalkenyl or arylalkyl, and (2) a heteroaryloxyacetamide of the general formula (II)
wherein R 4 means, respectively substituted alkyl, alkenyl, alkynyl or alkoxy, R 5 means, optionally substituted, alkyl, alkenyl, alkynyl or phenyl, and -i-R 6 signifies heteroaryl, if any, substituted, corresponding, in general , by 1 part by weight of the active compound of the general formula (I), from 0.001 to 1000 parts by weight of the active compound of the general formula (II). Of particular interest are the herbicidal agents according to the invention, characterized by a content of a combination of active compounds consisting of (1) a carbamoyltriazolinone of the formula (I), in which R 1 signifies hydrogen, hydroxy, amino, means alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylamino, alkenylamino, alkynylamino, alkylideneamino or dialkylamino, with respectively up to and including 6 carbon atoms, respectively substituted by halogen or cyano, means cycloalkyl, cycloalkylalkyl, with 3 to 6 carbon atoms respectively in the cycloalkyl group and, given, 1 to 4 carbon atoms in the alkyl group, substituted, if appropriate, by halogen, by cyano or by alkyl having 1 to 4 carbon atoms, or by phenyl or phenyl-alkyl with 1 to 4 carbon atoms, substituted respectively by halogen, by alkyl with 1 to 4 carbon atoms or by alkoxy with 1 to 4 carbon atoms, R2 means alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy.L, alkynyloxy, alkylthio, alkenylthio, alkynyl thio, alkylamino alkenylamino, alkynylamino or dialkylamino with respectively up to and including 6 carbon atoms, respectively substituted by halogen, by cyano, by alkoxy with 1 to 4 carbon atoms or by C 1 -C 4 -cytium means cycloalkyl, cycloalkyloxy or cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl group and, optionally, 1 to 4 carbon atoms in the alkyl group, respectively substituted in the case given by halogen, by cyano or by alkyl having 1 to 4 carbon atoms, or means phenyl, phenoxy, phenylthio, phenylamino or phenyl-alkyl having 1 to 4 carbon atoms, each substituted, if appropriate, by halogen, cyano, by alkyl with 1 to 4 carbon atoms or by alkoxy with 1 to 4 carbon atoms, and means alkyl, alkenyl, alkynyl with up to 10 carbon atoms inclusive, optionally substituted by halogen, by cyano, by alkoxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by alkylsulfinyl with 1 to 4 carbon atoms, by alkylsulfonyl with 1 to 4 carbon atoms, by alkylamino with 1 to 4 carbon atoms or by di- (alkyl with 1 to 4 carbon atoms) -amino, means cycloalkyl or cycloalkylalkyl with respectively 3 to 6 carbon atoms in the cycloalkyl part and, optionally, 1 to 4 carbon atoms in the alkyl part, optionally substituted by halogen, -e- by cyano or by alkyl with 1 to 4 carbon atoms, means phenyl-alkyl with 1 to 6 carbon atoms, phenyl-alkenyl with 2 to 6 carbon atoms or phenyl-alkynyl with 2 to 6 atoms of carbon, substituted, if appropriate, by halogen, by cyano, by alkyl with 1 to 4 carbon atoms or by alkoxy with 1 to 4 carbon atoms, and (2) a heteroaryloxyacetamide of the formula (II), in the R 4 means alkyl, alkenyl, alkynyl or alkoxy with up to and including 6 carbon atoms, each substituting, if appropriate, halogen, cyano or alkoxy with 1 to 4 carbon atoms, R 5 means alkyl, alkenyl or alkynyl with respect to vament.e up to 6 carbon atoms inclusive ive, respectively substituted, if appropriate, by halogen, by cyano or by alkoxy with 1 to 4 carbon atoms or by phenyl, optionally substituted by halogen, by cyano, by alkyl with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, for alkoxy with 1 to 4 carbon atoms or for halogenalkoxy with 1 to 4 carbon atoms, and R6 means heteroaryl, for the group consisting of 1,3-thiazol-2-yl, 1, 2,4-thiadiazol-5-yl, 1, 3, 5-thiadiazol-2-yl, benzoxazol-2-yl, benzothiazol-2-yl, optionally substituted by halogen, by cyano, by alkyl with 1 to 4 carbon atoms, by halogen-alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms or by haloalkoxy with 1 to 4 carbon atoms. Of particular interest are the herbal agents according to the invention, which are characterized in that they have a content in a combination of active compounds constituted by (1) a carbamoyltriazolinone of the formula (I), in which R 1 signifies hydrogen, hydroxy , Not me, means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, batenyl, propinyl or butynyl, methoxy, ethoxy, n-, i-propoxy, n-, i-, s- or t-butoxy, propenyloxy, butenyl-oxy, propynyloxy or butynyloxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, propenylamino, butenylamino, propynylamino or butylamino, ethylidenamino, propylideneamino, butylideneamino, dimethylamino or diethylamino respectively substituted, if appropriate by fluorine, chlorine or silt, means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, respectively substituted by fluorine by chlorine, by bromine, by cyano, by methyl, by ethyl, by n- or i-propyl, or by phenyl or benzyl, respectively substituted, respectively, by fluorine, by chlorine, by bromine, by cyano, by methyl , by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy or by ethoxy, - a -2 means methyl, ethyl , n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propinyl, butynyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, propenyloxy, butenyloxy, propynyloxy, butynyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, propenylthio, butenylthio, propinylthio, butinyl thio, methylamino, ethynyl, n- or i-propylamino, n-, i-, s- ot -butylamino, propenylamino, butenylamino, propynylamino, butynylamino, dimethylamino or diethylamino, respectively substituted, if appropriate, by fluorine, by chlorine, by cyano, by methoxy, by ethoxy, by n- or i-propoxy, by methylthio, by ethylthio, by n- or i-propylthio, means cyclopropyl, cyclobutyl, cyclopenyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, respectively substituted, if appropriate, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, or phenyl, phenoxy, fe nyl-, phenylamino or benzyl, respectively substituted, if appropriate, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -butyl, and R3 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, pentenyl, hexenyl, propynyl, butynyl, pentynyl or hexynyl, respectively substituted given by fluorine, by chlorine, by cyano, by ethoxy, by n- or i-propoxy, by n-, i-, s- or t-butoxy, by methylthio, by ethylthio, by n- or i-propyl- thio, by n-, i-, s- or t-butylthio, by methylsulfinyl, by ylsulphinyl, by methylsulfonyl, by ethylsulphonyl, by methylamino, by ethylamino, by n- or i-pro- pilamj.no, by n-, i-, s- or t-butylamino, by dimethylamino, by diethylamino, by dipropylamino or by dibuthylamine, means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutyl methyl, cyclopentylmethyl, cyclohexylmethyl. , cyclohexylethyl or cyclohexylpropyl, substituted respectively, where appropriate, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, or benzyl, phenylethyl, phenylpropyl, phenylbutyl, phenylethenyl, phenylpropenyl, phenylbutenyl, phenylene. , phenylpropynyl or phenylbutynyl, respectively substituted, if appropriate, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, by methoxy or ethoxy; and (2) a heteroaryloxyacetamide of the formula (II), wherein R 4 signifies methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propynyl, butynyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, substituted; respectively, where appropriate fluorine, chlorine, cyano, methoxy or ethoxy, R5 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i- , s- or t-pentyl, propenyl, butenyl, propyl or butynyl, respectively substituted, if appropriate, by fluorine, by chlorine, by cyano, by methoxy or by ethoxy, or by phenyl, optionally substituted by fluorine, by chlorine, by bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, and R6 is heteroaryl from the group consisting of 1,3-thiazol-2-yl, 1, 2, 4-thiadiazol-5-yl, 1,4-thiadiazol-2-yl, benzoxazol-2-yl, benzothiazol-2-yl, optionally substituted by fluorine, by chlorine, by bromine, by cyano, methyl, ethyl, n- or i- propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxy, ethoxy, n- or i-propoxy, by n-, i-, s- or t-butoxy, by difluoride xi or by trifluoromethoxy. As examples of the participants in the mixture according to the invention, corresponding to the compounds of the formula II), mention may be made in particular of: 4-amino-5-methyl-2- (1,1-dimethyl-ethyl-aminocarbonyl) -2, 4-dihydro-3H-1, 2,4-triazol-3-one, 4-amino-5-ethyl-2- (1,1-dimethyl-ethyl-aminocarbonyl) -2,4-dihydro- 3H-1, 2,4-triazol-3-one, 4-amin-5-n-propyl-2- (1,1-dimethyl-ethyl-aminocarbonyl) -2,4-dihydro-3H-1, 2, 4-triazol-2-one, 4-amino-5-i-propyl-2- (1, 1- dimethyl-ethyl-aminocarbonyl) -2,4-dihydro-3H-l, 2,4-triazole-3- ona, 4-amino-5-methoxy- 2- (1,1-dimethyl-ethyl-aminocarbonyl) -2,4-dihyd: ro-3H-1, 2,4-triazol-3-one, 4-amino- 5-Ethoxy-2- (1,1-dimethyl-ethyl-aminocarbonyl) -2,4-dihydro-3H-1, 2,4-triazol-3-one, 4-amino-5-methyl-2- (2 -f l-1, l-dimethyl-ethyl-aminocarbonyl) -2, -dihydro-3H-l, 2,4-triazol-3-one, 4-amino-5-ethyl-2- (2-fl uo : rl, 1-dimethyl-ethyl-aminocarbonyl) -2,4-dihydro-3H-1, 2,4-triazol-3-one, -amino-5-n-propyl-2- (2-fluoro-1, 1-di-methyl-ethyl-aminocarbonyl) -2,4-dihydro-3 Hl, 2,4-triazol-3-one, 4-amino-5-i-propyl-2- (2-fluoro-l, 1-dimethyl-ethyl-amino-carbonyl) -2,4-dihydro-3H- 1,2,4-triazol-3-one, 4-amino-5-me-toxy-2- (2-fluoro-1, 1-dimethyl-ethyl-aminocarbonyl) -2,4-dihydro-3H- 1,, 4-triazol-3-one, 4-amino-5-ethoxy-2- (2-f-lluor-1, 1-dimethyl-el: il-aminocarbonyl) -2,4-dihydro-3H-1, 2,4-triazol-3-one, 4-amino-5-methyl-2- (3-chloro-l, 1-dimethyl-ethyl-aminocarbonyl) -2,4-dihydro-3H-1, 2, 4-triazol-3-one, 4-amino-5-ethyl-2- (2-chloro-l, 1-dimethyl-ethyl-aminocarbonyl) -2,4-dihydro-3H-1,2,4-tri-zol -3-one, 4-amino-5-n-propyl-2- (2-chloro-1,1-dimethyl-ethyl-aminocarbonyl) -2,4-dihydro-3H-1, 2,4-triazole -3- one, 4-amino-5-i-propyl-2- (2-chloro-l, 1-dimethyl-ethyl-amino-carbonyl) -2,4-dihydro-3H-1, 2,4-triazole -3-one, 4-amino-5-methoxy-2- (2-chloro-1,1-dimethyl-ethyl-aminocarbonyl) -2,4-dihydro-3H-1, 2, -triazole-3- ona, 4-amino-5-ethoxy-2- (2-chloro-1,1-dimethyl-ethyl-aminocarbonyl) -2,4-dihydro-3H-1, 2,4-tri- azol-3-one, 4-amino-5-i-propyl-2-i-propyl-aminocar bonyl- 2,4-dihydro-3H-l, 2,4-triazol-3-one, 4-amino-5-dimethylamino- 2- (1,1-dit? ethyl-ethyl-aminocarbonyl) -2, 4- dihydro-3H-l, 2,4-triazol-3-one, 4-amino-5-dimethylamino-2- (2-f lura-1, ldi-methyl-ethyl-aminocarbonyl) -2,4-dihydro-3H -l, 2,4-triazol-3-one, 4-amino-5-dimethylamino-2- (2-chloro-l, 1-dimethyl-ethyl-aminocarbonyl) -2,4-dihydro-3H-1, 2 , 4-triazol-3-one and 4-methyl-5-methoxy- 2- (1,1-dimethyl-ethyl-aminocarbonyl) -2,4-dihydro-3H-l, 2,4-triazol-3-one . The compound 4-amino-5- (1-methyl-ethyl) -2- (1,1-di-methyl-ethyl-aminocarbonyl) -2,4-dihydro-3H-1, 2,4-triazole-3- ona - designated in the application examples as compound (1-1) - must be designated in a special manner as a component of the mixture of formula (I). As examples of the compounds of the formula (II), to be used as components of the mixtures according to the invention, mention may be made in particular of: N-methyl-N-phenyl-a- (5-trifluoromethyl-1,3,4- thiadiazol-2-yl-oxy) -acetyl, N-ethyl-N-phenyl-a- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy) -aceta ida, Nn-propyl-N -phenyl-a- (5- trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy) -acetamide, Ni-propyl-N-phenyl-OI- (5-trifluoromethyl-1,3,4-thiadiazole- 2-yl-oxy) -acetamide, N-methyl-N- (4-fluoro-phenyl) -OÍ- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy) -acetamide, N -ethyl-N- (4- fluoro-phenyl) -o; - (5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy) -acetamide, Nn-propyl-N- (4-fluoro-phenyl) -a- (5-trifluoromethyl), 3,4 -thiadiazol-2-yl-oxy) -acetamide, Ni-propyl-N- (4-fluorophenyl) -a-! 5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy) -aceta- Measure, N-mstyl-N- (4-chloro-phenyl) -a- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy) -acetamide, N-ethyl-N- (4-chloro) phenyl) -a- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy) -acetamide, -n-propyl-N- (4-chloro-phenyl) -a- (5-trifluoromethyl) 1, 3, 4-thiadia-zol-2-yl-oxy) -acetamide and Ni-propyl-N- (4-chloro-phenyl) -a- (5-trifluoromethyl-1,3,4-thiadiazole-2-) il-oxy) -acetamide. The compound Ni-propyl-N- (4-fluoro-phenyl) -a- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy) -acetamide - designated in the application examples as compounds (II -l) - must be singled out as a component of the mixture of formula (II). The compounds of the formulas (I) and (II) have been described in the patent applications or in the specifications of the aforementioned patents. It has now been found, surprisingly, that the above defined active compound combinations, consisting of carbamoyltriazolinones of the formula (I) and the heteroaryloxyacetamides of the formula (II), exhibit a particularly high herbicidal activity and that they can be used in various crops for the selective fight against weeds. Surprisingly, the herbicidal activity of the active compound combinations according to the invention is considerably greater than the sum of the effects of the individual active products. Therefore a real synergistic effect is not predictable and not only a complement of the effects. The new combinations of active products are perfectly compatible with many crops, attacking the new combinations of active products also with weeds that are difficult to combat otherwise, such as Portulace and Xanthium types. The new combinations of active products therefore represent a valuable enrichment of the selective herbicides. The active compound combinations according to the invention can be used, for example, on the following plants: Dicotyledonous bad herbs of the kinds; Sinapis, Lepi-dium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodi m, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Co volvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Sida, Datura, Viola, Geleo-psis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxum. Dicotyledonous crops of the classes; Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vivia, Ni otiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita. Bad monocotyledonous herbs of the kinds; Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Oats, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactylloctenium, Agrostis, Alopecurus, Apera. Monocotyledonous crops of the classes; Oryza, Zea, Tricicuym, Hordeum, Oats, Sécale, Sorghum, Panicum, Saccha-rum, Ananas, Asparagus, Allium. The use of the combinations of active compounds according to the invention is, however, not limited in any way to these classes, but they also extend equally over other plants. The synergistic effect of the active compound combinations according to the invention is especially marked with certain concentration ratios. However, the proportions by weight of the active products in the combinations of active products can vary within: a relatively broad range. In general, they correspond, per 1 part by weight of active compound of the formula (I), from 0.001 to 1000 parts by weight, preferably 0, From 1 to 100 parts by weight and, especially preferably, from 0.1 to 10 parts by weight of active compound of the formula (II). The active compounds can be converted into the customary formulations, such as solutions, emulsions, sprayable powders, suspensions, powders, dusting agents, pastes, soluble powders, suspension-emulsion concentrates, natural and synthetic materials impregnated with the active compound, as micro-encapsulated in polymer materials. These formulations are prepared in a known manner, for example by mixing the active ingredients with extender materials, that is, with liquid solvents and / or solid excipients, where appropriate, using surfactants, that is, emulsifiers and / or dispersants. I'o foam generating means. In the case of using water as extender, for example, organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are, in particular, aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexanes. hexane or paraffins, for example, fractions of crude oil, mineral and vegetable oils, alcohols, such as butanol, or glycol, as well as their esters and ethers, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, as well as water. Suitable solid excipients are, for example, ammonium salts and natural molten minerals, such as kaolins, clays, talc, chalk, quartz, attapalgite, montmorillonite or diatomaceous earth and molten synthetic minerals, such as acid. silicon, highly dispersed, aluminum oxide and silicates as solid excipients for granulates come into consideration: for example, broken and fractionated natural minerals such as calcite, marble, pumice, sepiolite, dolomite, as well as synthetic granules of inorganic and organic flours, as well as granulates of organic materials, such as sawdust, coconut husks, corn ears and tobacco stems; Examples of suitable emulsifiers and / or foam generators are: nonionic and anionic emulsifiers, such as polyoxyethylenated esters of fatty acids, for example, alkylaryl polyglycol ether, alkylsulfonates, alkyl sulfates, arylsulphonates, such as albumin hydrolysates; Suitable dispersants are, for example, lithium lixivities of lignin and methylcellulose. In the formulations, adhesives such as carboxymethylcellulose, natural and synthetic polymers powdery, granulated or in the form of latex, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids, such as cephalin and lecithin, and synthetic phospholipids. Other additives can be mineral and vegetable oils. Dyes, such as inorganic pigments, for example, iron oxide, titanium oxide, ferrocyanic blue and organic dyes, such as alizarin dyes, metal azo and phthalocyanine dyes and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. The formulations usually contain between 0,:. up to 95% by weight of active substance, preferably between 0.5 and 90%. The combinations of active products according to the - 1? -invention will be used, in general, as formulations ready for their use. The active products, contained in the combinations of active products, can be mixed in the case of; its application, in individual formulations, that is to say that they can be used in the form of tank mixes. The new active compound combinations can find application as such or in their formulations as well as in a mixture of other known herbicides, while ready-to-use formulations or tank mixtures are also possible. A mixture with other known active substances is also possible, such as fungicides, insecticides, acaricides, nematicides, protective substances against ingestion by birds, growth substances, nutrient substances of the plants and means for improving the structure of the ground. For certain purposes of application, especially in the post-sprouting process, it may also be advantageous to incorporate, in the form of other additional products, mineral or vegetable oils compatible with the plants (for example the usual "Oleo Dupont HE"). in commerce) or cthmonium salts, such as, for example, ammonium sulfate or ammonium rhodanide. The novel active compound combinations according to the invention can be used as such, in the form of their formulations or of the forms of application prepared therefrom by further dilutions, such as ready-to-use solutions, suspensions, emulsions, powders, pastes. and granulates. The use is carried out in the usual way, for example, by watering, spraying, spraying, spreading. The application rates of the active compound combinations according to the invention may vary within certain limits; These depend, among other things, on the climatology and the terrain factors. In general, the application amounts are between 5 g and 5 kg per ha, preferably between 20 g and 20 kg per ha, particularly preferably between 50 g and 1.0 kg per ha. The active compound combinations according to the invention can be applied both before and after the outbreak of the plants, ie in pre-emergence and post-emergence procedures. The good herbicidal effect of the new combinations can be seen by means of the following examples. While the individual active products have weaknesses in their herbicidal effect, the combinations present, as a rule, a very good weed-destroying effect, which goes beyond the simple sum of the effects. A synergistic effect is presented in the herbicides provided that the herbicidal effect of the combination of the active products is greater than that of the active products applied individually. The expected effect for a given combination of two herbicides can be calculated as follows (see Colby, S. R.; "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, pages 20-22, 1967): If X =% damage caused by herbicide A (active product of formula I) with an application amount p kg / ha and Y =% damage caused by herbicide B (active product of formula II) with an application amount q kg / ha and E = expected damage caused by herbicides A and B with application quantities p and q kg / ha, then E = X + Y- (X * Y / 100).
If the actual damage is greater than calculated, then the combination will be over-additive in its effect, that is to say it shows a synergistic effect. It is clear from the following examples that the herbicidal effect of the active compound combinations according to the invention on weeds is greater than that calculated, that is to say that the new combinations of active compounds have a synergistic effect. Application examples For the preparation of the preparations of active ingredients necessary according to the invention, the corresponding amounts of a water-dispersible powder formulation (P) of a carbamoyltriazo-linone of the formula (I) and a powdery formulation (WP) are weighed. water dispersible heteroaryloxy acetamide of the formula (II) and diluted with water to the desired concentration. The tests were carried out as follows: Pre-sprout / greenhouse test Seeds of the test plants are planted in normal soils and watered, after 24 hours, with the preparation of active product. In this case, the amount of water per unit area is kept constant conveniently. The concentration of active product in the preparation plays no role; the fundamental thing is only the sanctity used for the active product per unit area. After the treatment the test plants are kept in the greenhouse, under controlled conditions (temperature, humidity, light) until the evaluation. After three weeks the degree of deterioration of the plants is evaluated in% of damages compared to the development of the untreated control plants. Means: 0 = no effect / no damage (like untreated controls) 100 = total destruction. The active products, the application quantities and the results can be seen, respectively, by means of the following tables, the abbreviations used in the tables having the following meanings: gef. = damage found or effect (in%). ber. = damage calculated according to the Colby formula or effect (in%). to. i. = "active ingredient" = active substance. Table 1; Pre-emergence / winter trial
Prod. Or Comb. = Active product or combination of active products Qty = amount used Table 2; Ensa or re-brot
Prod. Or Comb. = Active product or combination of active products Qty = quantity used It is noted that, in relation to this date, the best method known by the applicant to carry out the aforementioned invention, is that which is clear from the present. and description of the invention. Having described the invention as above, the content of the following is claimed as property:
Claims (7)
- - 2 - CLAIMS 1.- Herbicidal agents, characterized in that they have a content of a combination of active compounds constituted by (1) a carbamoyltriazolinone of the general formula (I) wherein R 1 signifies hydrogen, hydroxy, amino or means, respectively substituted, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylamino, alkenylamino, alkynylamino, alkylideneamino, dialkylamino, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl R 2 means, where appropriate substituted, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylamino, alkenylamino, alkynylamino, dialkylamino, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, aryl, aryloxy, arylthio, arylamino or arylalkyl and R3 means, optionally substituted, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, arylalkyl, arylalkenyl or arylalkyl, and (2) a heteroaryloxyacetamide of the general formula (II) wherein R 4 means, respectively substituted, alkyl, alkenyl, alkynyl or alkoxy, R 5 means, optionally substituted, alkyl, alkenyl, alkynyl or phenyl, and R 6 means optionally substituted heteroaryl, corresponding, in general, per 1 part by weight of the active ingredient of the general formula (I), from 0.001 to 1000 parts by weight of the active compound of the general formula (II).
- 2. The herbicidal agent according to claim 1, characterized in that the active compound combination is constituted by (1) a carbamoyltriazolinone of the formula ([), in which R1 signifies hydrogen, hydroxy, amino, means alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylamino, alkenylamino, alkynylamino, alkylideneamino or dialkylamino, with up to and including 6 carbon atoms, respectively substituted, if appropriate, by halogen or cyano, means cycloalkyl, cycloalkylalkyl, respectively 3 to 6 carbon atoms in the cycloalkyl group and, optionally, 1 to 4 carbon atoms in the alkyl group, optionally substituted by halogen, by cyano or by alkyl with 1 to 4 carbon atoms, or by phenyl or phenyl -alkyl with 1 to 4 carbon atoms, substituted respectively by halogen, by alkyl with 1 to 4 carbon atoms or by alkoxy with 1 to 4 carbon atoms, meaning alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynyl thio, alkylamino, alkenylamino, alkynylamino or dialkylamino with respectively up to and including 6 carbon atoms, respectively substituted by halogen, by cyano, by alkoxy with 1 to 4 carbon atoms or alkylthio having 1 to 4 carbon atoms means cycloalkyl, cycloalkyloxy or cycloalkylalkyl with 3 to 6 carbon atoms in the cycloalkyl group and, optionally, 1 to 4 carbon atoms in the group alkyl, respectively substituted, if appropriate, by halogen, by cyano or by alkyl having 1 to 4 carbon atoms, or by phenyl, phenoxy. phenylthio, phenylamino or phenyl-C 1 -C 4 -alkyl, optionally substituted by halogen, by cyano, by C 1 -C 4 -alkyl or by C 1 -C 4 -alkoxy, and R 3 means alkyl, alkenyl, alkynyl with up to and including 10 carbon atoms, optionally substituted by halogen, by cyano, by alkoxy with]. to 4 carbon atoms, for alkylthio with 1 to 4 carbon atoms, for alkylsulfinyl with 1 to 4 carbon atoms, for alkylsulfonyl with 1 to 4 carbon atoms, for alkylamino with 1 to 4 carbon atoms or for di- ( alkyl with 1 to 4 carbon atoms) -amino, means cycloalkyl or cycloalkylalkyl with respectively 3 to 6 carbon atoms in the cycloalkyl part and, optionally, 1 to 4 carbon atoms in the alkyl part, optionally substituted by halogen, by cyano or by alkyl with 1 to 4 carbon atoms, means phenyl-C 1-6 alkyl, phenyl-C 2-6 alkenyl or phenyl-alkynyl with 2 a 6 carbon atoms, substituted, if appropriate, by halogen, by cyano, by alkyl with 1 to 4 carbon atoms or by alkoxy with 1 to 4 carbon atoms, and (2) a heteroaryloxyacetamide of the formula (II), wherein R4 means alkyl, alkenyl, alkynyl or alkoxy with respectively up to and including 6 carbon atoms, respectively substituted, if appropriate, by halogen, by cyano or by alkoxy with 1 to 4 carbon atoms, R5 means alkyl, alkenyl or alkynyl with respect to - optionally up to and including 6 carbon atoms, optionally substituted by halogen, by cyano or by alkoxy with 1 to 4 carbon atoms or by phenyl, optionally substituted by halogen, by cyano, by alkyl with 1 to 4 carbon atoms carbon, by halogenalkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms or by halogenalkoxy with 1 to 4 carbon atoms, and R6 means heteroaryl, from the group consisting of 1,3-thiazol-2 -yl, 1, 2,4-thiadiazol-5-yl, 1, 3, 5-thiadiazol-2-yl, benzoxazol-2-yl, benzothiazol-2-yl, optionally substituted by halogen, by cyano, by alkyl with 1 to 4 carbon atoms, by halogen-alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms or by halogenalkoxy with 1 to 4 carbon atoms.
- 3. The herbicidal agent according to claim 1, characterized in that the active compound combination consists of (1) a carbamoyltriazolinone of the formula (I), in which R1 signifies hydrogen, hydroxy, amino, means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propinyl or butynyl, methoxy, ethoxy ,. n-, i-propoxy, n-, i-, s- or t-butoxy, propenyloxy, butenyl-oxy, propynyloxy or butynyloxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, prope-nilamino, butenylamino, propynylamino or butynylamino, ethylideneamino, propilidenamino, butilidenamino, dime-methyl-amino or diethylamino substituted in each case optionally fluorine-, chlorine- or mire, means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, or represents phenyl or benzyl substituted in each case optionally fluorine-, doro, by bromine, by cyano, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy or by ethoxy, means methyl, ethyl, n- or i- propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl, butynyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, propenyloxy, butenyloxy, propynyloxy, butynyloxy, ethylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-bu- methylthio, propenylthio, butenylthio, propynylthio, butynyl thio, methylamino, ethylamino, n - or i-propylamino, n-, i-, s- or t-butylamino, propenylamino, butenylamino, propylene nilamino, butynylamino, dimethylamino or diethylamino, each substituted optionally by fluorine, chlorine, cyano, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-pro-piltio, means cyclopropyl, cyclobutyl, ciclopen, cyclohexyl, cyclopropyloxy, cyclobutyloxy, ci-clopentiloxi, cyclohexyloxy, cyclopropylmethyl, cyclo butylmethyl, cyclopentylmethyl or cyclohexylmethyl, in each case optionally substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, or represents phenyl, phenoxy, phenyl-thio, phenylamino or benzyl, respectively substituted, if appropriate, by fluorine, by chlorine, by bromine, by cyano, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, and means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-but: Llo, propenyl, butenyl, pentenyl, hexenyl, propynyl, butynyl, pentynyl or hexynyl, respectively substituted, if appropriate, by fluorine, by chlorine, by cyano. by ethoxy, by n- or i-propoxy, by n-, i-, s- or t-butoxy, by methylthio, by ethylthio, by n- or i-propylthio, by n-, i-, s- or t-butylthio, for methylsulfinyl, for ethylsulfinyl, for methylsulphonyl, for ethylsulphonyl, for methylamino, for ethylamino, for n- or i-propylase, for n-, i-, s- or t-butylamino , by dimethyl amino. by diethylamino, by dipropylamino or by dibuthylamino, means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutyl methyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexyl or cyclohexylpropyl, respectively substituted, if appropriate, by fluorine, by chlorine , by bromine, by cyano, by methyl, by ethyl, by n- or i-propyl, or means benzyl, phenylethyl, phenylpropyl, phenyl butyl, phenylethenyl, phenylpropenyl, phenylbutenyl, phenylethynyl, phenylpropynyl or phenylbutynyl, respectively substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy, and (2) a heteroaryloxyacetamide of the formula (II), wherein R 4 signifies methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, propenyl, butenyl, propinyl, butynyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, respectively substituted, if appropriate, by fluorine, by chlorine, by cyan or, by methoxy or by ethoxy, R5 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, propenyl, butenyl, propinyl or butynyl, optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, or phenyl, optionally substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl , by trifluoromethyl, by methoxy, by ethoxy, by difluoromethoxy or by trifluoromethoxy, and R6 means heteroaryl from the group consisting of 1,3-thiazol-2-yl, 1, 2, 4-thiadiazol-5-yl, 1, 3, 4-thiadiazol-2-yl, benzoxazol-2-yl, benzothiazol-2-yl, optionally substituted, if appropriate, by fluorine, by chlorine, by bromine, by cyano, by methyl, by ethyl, by n- or by - propyl, by n-, i-, s- or t-butyl, by difluoromethyl, by trifluoromethyl, by dichloromethyl, by trichloromethyl, by methoxy, by ethoxy, by n- or i-propoxy, by n-, i -, s- or t-butoxy, by difluoromethoxy or by tri- fl uort? ethoxy.
- 4. - Herbicidal agent according to claims 1 to 3, characterized in that in the active compound combinations the weight ratio between the active compound of the formula (I) and the active compound of the formula (II) is between 1: 0.01 t 1: 100, especially between 1: 0.1 and 1:10.
- 5. - Procedure for the fight against weeds, characterized in that a combination of active products according to claims 1 to 3 is allowed to act on the weeds or on their environment.
- 6. - Use of the combinations of active products according to the Claims 1 to 3 for the fight against weeds.
- 7. Process for obtaining herbicidal agents, characterized in that a combination of active products according to claims 1 to 3 is mixed with extenders and / or surfactants. In testimony of which I sign this in this Mexico City, D.F. By: BAYER AKTIENGESELLSCHAFT
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4437049.0 | 1994-10-17 | ||
| DE4437049A DE4437049A1 (en) | 1994-10-17 | 1994-10-17 | Selective herbicides based on carbamoyltriazolinones and heteroaryloxyacetamides |
| PCT/EP1995/003906 WO1996011575A1 (en) | 1994-10-17 | 1995-10-04 | Selective herbicides based on carbamoyltriazolinones and heteroaryloxyacetamides |
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| Publication Number | Publication Date |
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| MXPA97002552A true MXPA97002552A (en) | 1997-06-01 |
| MX9702552A MX9702552A (en) | 1997-06-28 |
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| MX9702552A MX9702552A (en) | 1994-10-17 | 1995-10-04 | Selective herbicides based on carbamoyltriazolinones and heteroaryloxyacetamides. |
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| Country | Link |
|---|---|
| US (1) | US5811373A (en) |
| EP (1) | EP0786938A1 (en) |
| CN (1) | CN1076585C (en) |
| AU (1) | AU3803595A (en) |
| BR (1) | BR9509362A (en) |
| DE (1) | DE4437049A1 (en) |
| HU (1) | HU223670B1 (en) |
| MX (1) | MX9702552A (en) |
| WO (1) | WO1996011575A1 (en) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2128984B1 (en) * | 1996-05-24 | 2000-02-01 | Bayer Ag | HERBICIDES BASED ON HETEROARILOXI-ACETAMIDAS FOR USE IN RICE CULTIVATION. |
| AU771265B2 (en) | 1999-09-30 | 2004-03-18 | Bayer Aktiengesellschaft | Selective herbicides on the basis of N-aryl-triazoline(thi)ones |
| DE10041619A1 (en) | 2000-05-22 | 2001-11-29 | Bayer Ag | Selective herbicides based on heteroaryloxyacetamides |
| AU2001265936B2 (en) * | 2000-05-22 | 2006-04-06 | Bayer Intellectual Property Gmbh | Selective heteroaryloxy-acetamide-based herbicides |
| MX339832B (en) * | 2009-06-09 | 2016-06-14 | Arysta Lifescience Corp | Carbamoyl triazolinone based herbicide combinations and methods of use. |
| US10299479B2 (en) | 2009-06-09 | 2019-05-28 | Arysta Lifescience Corporation | Carbamoyl triazolinone based herbicide combinations and methods of use |
| HRP20161112T1 (en) * | 2009-12-17 | 2016-12-02 | Bayer Intellectual Property Gmbh | Herbicides comprising flufenacet |
| WO2011082954A2 (en) * | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbicidal agents containing flufenacet |
| WO2011082959A2 (en) | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbicidal agents containing flufenacet |
| DK2515658T3 (en) * | 2009-12-17 | 2016-09-12 | Bayer Ip Gmbh | HERBICIDE AGENTS CONTAINING FLUFENACET |
| DK2512248T3 (en) | 2009-12-17 | 2016-11-21 | Bayer Ip Gmbh | HERBICIDE AGENTS CONTAINING FLUFENACET |
| WO2011082955A2 (en) * | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbicidal agents comprising flufenacet |
| WO2011082956A2 (en) | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbicidal agents containing flufenacet |
| WO2011082953A2 (en) | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbicidal agents comprising flufenacet |
| WO2011082968A2 (en) * | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbicidal agents containing flufenacet |
| WO2011082964A1 (en) | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbicidal agents containing flufenacet |
| WO2011082957A2 (en) * | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbicidal agents containing flufenacet |
| WO2014001361A1 (en) | 2012-06-27 | 2014-01-03 | Bayer Cropscience Ag | Herbicidal agents containing flufenacet |
| WO2014001248A1 (en) | 2012-06-27 | 2014-01-03 | Bayer Cropscience Ag | Herbicidal compositions comprising flufenacet |
| WO2014001357A1 (en) | 2012-06-27 | 2014-01-03 | Bayer Cropscience Ag | Herbicidal agents containing flufenacet |
| ES2714929T3 (en) | 2012-06-27 | 2019-05-30 | Bayer Cropscience Ag | Herbicidal agents containing flufenacet |
| EP2936983A1 (en) | 2014-04-25 | 2015-10-28 | Bayer CropScience AG | Compound for increase of yield in cotton |
| CN105660661B (en) * | 2016-03-18 | 2018-08-17 | 哈尔滨利民农化技术有限公司 | A kind of cornfield weeding composition and its application method |
| BR102018075132A2 (en) | 2018-12-04 | 2020-06-16 | UPL Corporation Limited | WIDE SPECTRUM SYNERGISTIC HERBICIDE COMPOSITION FOR THE CONTROL OF WEEDS IN AGRICULTURAL CROPS, USE OF THESE COMPOSITION FOR PREPARATION OF PRODUCT, PRODUCT AND APPLICATION METHOD |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3803523A1 (en) * | 1987-06-12 | 1988-12-22 | Bayer Ag | SUBSTITUTED TRIAZOLINONES |
| DE3821600A1 (en) * | 1988-06-27 | 1989-12-28 | Bayer Ag | HETEROARYLOXYACETIC ACID-N-ISOPROPYLANILIDE |
| DE4005930A1 (en) * | 1990-02-25 | 1991-08-29 | Bayer Ag | SELECTIVE HERBICIDES, CONTAINING ETHOFUMESATE, PHENMEDIPHAM, CHLORIDAZONE OR QUINMERAC IN COMBINATION WITH CERTAIN TRIAZOLINONES |
| DE4223465A1 (en) * | 1992-07-16 | 1994-01-20 | Bayer Ag | Herbicidal agents based on heteroaryloxyacetamides |
-
1994
- 1994-10-17 DE DE4437049A patent/DE4437049A1/en not_active Withdrawn
-
1995
- 1995-10-04 WO PCT/EP1995/003906 patent/WO1996011575A1/en not_active Ceased
- 1995-10-04 AU AU38035/95A patent/AU3803595A/en not_active Abandoned
- 1995-10-04 BR BR9509362A patent/BR9509362A/en not_active IP Right Cessation
- 1995-10-04 US US08/817,361 patent/US5811373A/en not_active Expired - Lifetime
- 1995-10-04 MX MX9702552A patent/MX9702552A/en unknown
- 1995-10-04 CN CN95195704A patent/CN1076585C/en not_active Expired - Lifetime
- 1995-10-04 HU HU9701866A patent/HU223670B1/en not_active IP Right Cessation
- 1995-10-04 EP EP95935895A patent/EP0786938A1/en not_active Ceased
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