N-aryl-uracile-based herbicides

专利摘要:
The present invention also relates to the known N-aryl-uracil and, on the other hand, compounds which improve the compatibility with known herbicidally active compounds and / or crops and which, among the various crops useful in their use, To novel herbicidal formulations which are capable of exhibiting particularly good results in controlling not only peat and twill weeds in semi-and non-selective areas as well as in control.
公开号:KR20020059758A
申请号:KR1020027006457
申请日:2000-11-21
公开日:2002-07-13
发明作者:호이흐트디터；다멘페터；드레베스마르크빌헬름；크라우스코프비르기트；크레머마티아스；폰트젠롤프；벳초로프스키인고；안드레롤란트
申请人:빌프리더 하이더；바이엘 악티엔게젤샤프트；
IPC主号:

专利说明:

N-aryl-uracil-based herbicides < RTI ID = 0.0 >
[1] The present invention also relates to the known N-aryl-uracil and, on the other hand, compounds which improve the compatibility with known herbicidally active compounds and / or crops and which, among the various crops useful in their use, To novel herbicidal formulations which are capable of exhibiting particularly good results in controlling not only peat and twill weeds in semi-and non-selective areas as well as in control.
[2] N-Aryl-Uracyl is patented as a herbicidally active substance in several patent applications (cf. EP-A-408382, EP-A-473551, EP-A-563384, EP- WO-A-95/29168, WO-A-95/30661, WO-A-96/35679, WO- WO-A-97/01541, WO-A-98/25909). However, the known N-aryl-uracil has many deficiencies in its activity.
[3] A number of herbicidal combinations based on N-aryl-uracil are also known (DE-A-4437197, DE-A-19915013, DE-A-19919951, EP- 07323, WO-A-96/08151, JP-A-11189506). However, likewise, the properties of these active formulations are not very satisfactory.
[4] Surprisingly, it has been found that when a large number of known active compounds selected from N-aryl-uracil groups according to the present invention are used in combination with known herbicidally active compounds, they show a synergistic effect in terms of activity against weeds, Control of monocotyledonous and dicotyledonous weeds in semi-and non-selective areas as well as selective control of monocotyledonous and dicotyledonous weeds in crops, grains, grasses / pastures, maize, lawns, rice, soybeans, sunflowers and sugarcane It has been found that it can be used particularly advantageously as a broad active compounding agent.
[5] The present invention
[6] (a) at least one N-aryl-uracil of the general formula (I) (" active compound of group 1 &
[7] (b) 2-Chloro-N- (ethoxymethyl) -N- (2-ethyl-6-methyl-phenyl) -acetamide (acetochlorine) Phenoxy) -2-nitro-benzoic acid sodium salt (acifluorfen-sodium), 2-chloro-6-nitro- ) -N- (2,6-diethyl-phenyl) -acetamide (allachlor), N-ethyl-N'-i-propyl-6-methylthio-1,3,5-triazine- - diamine (ametryne), 4-amino-N- (1,1-dimethyl-ethyl) -4,5-dihydro- 4-triazole-1-carboxamide (Amicabazone), N- (4,6-dimethoxy-pyrimidin- ) - urea (amidosulfuron), 1H-1,2,4-triazole-3-amine (amitrol), 6-chloro- Azine (atrazine), 2- [2,4-dichloro-5- (2-propynyloxy) -phenyl] -5,6,7,8-tetrahydro-1,2,4- triazolo- [ 3, a] -pyridin-3 (2H) -one ( Methyl-4- (2-methyl-2H-tetrazol-5-yl) -lH-quinazolin- Benzyl-2- (4-fluoro-3-trifluoromethyl-phenoxy) -butanamide (beflubutamide), 4- N-butyl-N-ethyl-2,6-dinitro-4-trifluoromethyl-benzenamine (benz flouraline), Methyl-2- [2- [4- (2-methoxycarbonylphenylmethylsulfonyl) -urea (benzenesulfonyl) Methyl-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinyl) phenoxy] methyl] -5-ethyl-phenoxy- Yl) -4-phenylthio-bicyclo- [3.2.1] -oct-3-en-2-one (benzoficyclone), 3- (2-chloro-4-methylsulfonyl- Benzyl-N- (3,4-dichloro-phenyl) -DL-alaninate (benzoylprop-ethyl), 3-i-propyl-1H-2,1,3-benzothiadiazole -4 (3H) -one (benzazone), methyl 5- (2,4-dichloro-phenoxy) -2-nitro- benzoate (bifenox), 2,6- (LH, 3H) - benzoic acid sodium salt (bispyryl-sodium), 5-bromo-6-methyl-3- (2-bromo-3,3-dimethyl-N- (1 -methyl-1-phenyl- ethyl) -butanamide (bromobutide), O- 4-hydroxy-benzonitrile (bromocinnamyl), N- (4-hydroxy-benzoyl) (2-propenyloxy)] - (2-fluoro-phenyl) -acetamide Ethyl 2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l (2H) -pyrimidinyl) -benzoate (butapenacyl- Allyl), 2- (1-ethoximino-propyl) -3-hydroxy-5- [2,4,6-trimethyl- -On (Butyloxydim), S-ethylbis- (2-methyl-propyl) -thiocarbamate (butylate), N, 2-propenyl) -oxy-imino] -propyl] -3- (3-chloro-2- 2-cyclohexen-1-one (carboxydim, teflaloxydim), 2- (4-chloro-2-fluoro- - (2-chloro-2-ethoxycarbonyl-ethyl) -phenyl) -4-difluoromethyl-5-methyl- Benzene (chloromethoxyphene), 3-amino-2,5-dichloro-benzoic acid (chloromethoxyphene), 3-amino- (Chloromethyl-ethyl), (4-chloro-6-methoxy-pyrimidin-2-yl) Methoxy-6-methyl-1,3,5-triazine-2- (4-nitro-phenoxy) Yl) -N ' - (2-chloro-phenylsulfo Chloro-3- [2-chloro-4-methyl-phenyl) -N, N-dimethyl-urea (chlorotoluron) Yl) -phenyl] -2-propanoate (cinidon-ethyl), < RTI ID = 0.0 & (4,6-dimethoxy-1,3,5-triazin-2-yl) -N '- (2- (2-methoxy-ethoxy) -phenyl- sulfonyl) Furon), 2- [l- [2- (4-chloro-phenoxy) -propoxyamino] butyl] -5- (tetrahydro-2H-thiopyran- (Clexidim), (E, E) - (+) - 2- [1 - [[(3-chloro-2- propenyl) (4-chloro-3-fluoro-pyridin-2-yl-oxy) -phenoxy] - Chloro-2 - [(5-ethoxy-7-fluoro [1,2 < / RTI > , 4] triazolo [1,5-c] pyrimidin-2-yl-sulfonyl) - Amino] -benzoate (chloranesulam-methyl), 2-chloro-4-ethylamino-6- (1-cyano- (2-cyclopropylcarbonyl-phenylsulfonyl) -urea (cyclosulfamuron), 2- (1-ethoximino Butyl) -3-hydroxy-5- (tetrahydro-2H-thiopyran-3-yl) -2-cyclohexen- 2-fluoro-phenoxy) -phenoxy] -propanoate (cyhalofop-butyl), 2,4-dichloro-phenoxyacetic acid (2,4- Dichloro-2-methoxy-benzoic acid (dicamba), (R) -2- (2,4-dichloro-phenoxy) propanoic acid (dichlorprop- Dichloro-phenoxy) -phenoxy] -propanoate (diclofop-methyl), N- (2,6-dichloro-phenyl) -5-ethoxy- 4] -triazolo- [1,5-c] -pyrimidine-2-sulfonamide (diclosylam), 1,2-dimethyl-3,5-diphenyl-1H-pyrazolium methyl 2 (2-trifluoromethyl-phenoxy) -pyridine-3-carboxamide (difluorenecane), 2 (Diphenylphosphon), S- (1-methyl-1-phenyl-ethyl) -pyridine- (2-methoxy-ethyl) -acetamide (prepared from 2-chloro-N- (2,6-dimethyl- Dimerchlor), (S-) 2-chloro-N- (2,4-dimethyl-3-thienyl) -N- (2-methoxy- Methyl-ethyl) -6- (1-methyl-2- (3,5-dimethyl-phenoxy) -ethylamino) -1, N3, diethyl-2,4-dinitro-6-trifluoromethyl-1,3-diamino-benzene (dinitramine), 6,7 -Dihydro-dipyrido [1,2-a: 2 ', 1'-c] pyrazine di (dicouat), S, S-dimethyl 2-difluoromethyl- Fluoromethyl- (Dithiophene), N '- (3,4-dichloro-phenyl) -N, N-dimethyl- (Phenyl) -oxiranylmethyl] -2-ethyl-1H-indene-1,3 (2H) -dione (Ephroptan), S- ethyldipropylthiocarbamate Ethyl-N- (2-methyl-2-propenyl) -2,6-dinitro-4-tricarboxylic acid (S) -2-chloro-5- (2-chloro-4-trifluoromethyl-phenoxy) -pyridin- - (2-ethoxy-phenoxylphenyl) -urea (ethoxylated furon), ethyl (2-methoxyphenoxy) (Phenoxaprop- (P) -ethyl), 4- (2-chloro- benzooxazol-2-yl-oxy) -phenoxy] Phenyl) -N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide (pentrazamid), isopropyl N- (3-chloro-4-fluoro-phenyl) -DL-alaninate (flampprop-isopropyl), isopropyl N-benzoyl-N- ) -L-alaninate (flampprop-isopropyl-L), methyl N-benzoyl-N- (3-chloro-4-fluoro-phenoxy) ), N- (2,6-difluoro-phenyl) -8-fluoro-5-methoxy- [1,2,4] -triazolo- [1,5- c] pyrimidin- (Fluorazifop, -butyl, - (R) -2- [4- (5-trifluoromethyl-pyridin-2-yl-oxy) -phenoxy] Methyl-5-trifluoromethyl-lH-pyrazol-3-yl) -2-chloro-4-fluoro-benzoate (flu- Dihydro-3-methoxy-4-methyl-5-oxo-N - [(2-trifluoromethoxy- phenyl) -sulfonyl] Triazole-1-carboxamide sodium salt (flucarbazone-sodium), N- (4-fluoro-phenyl) (2,2-difluoro-phenyl) -5-methyl-1,2, < / RTI > (2-chloro-4-fluoro-5- (1, 3, 4, 5, 6, 7) -triazolo [1,5-a] -pyrimidine- -Hexahydro-1,3-dioxo-2H-isoindol-2-yl) -phenoxy] -acetate (fumiclolactopentyl), 2- [7-fluoro-3,4- 4- (2-propynyl) -2H-1,4-benzoxazin-6-yl] -4,5,6,7-tetrahydro-1H-isoindole- Methyl-2-propynyl) -oxy] -phenyl] -4,5,6,7-tetrahydro-1H-iso Indole-1,3 (2H) -dione (flumiprofen), 3-chloro-4-chloromethyl-1- (3-trifluoromethyl- phenyl) -2- pyrrolidone (fluorochloridone) (Fluoroglycophene-ethyl), 1- (4-chloro-3- (2 (trifluoromethyl) , 2,3,3,3-pentafluoro-propoxy Methyl-phenyl) -5-phenyl-1H-1,2,4-triazole-3-carboxamide (fluoxam), 1-isopropyl- Methyl-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidyl) -benzoate (fluproprosyl), N- (4,6- dimethoxy-pyrimidin- -Urea sodium salt (flupyrsulfuron-methyl-sodium), 9-hydroxy-isoquinolin-2-yl) (4-amino-3,5-dichloro-6-fluoro-pyridin-2-yl-oxy) -acetic acid (2-butoxy- (3-trifluoromethyl-phenyl) -3 (2H) - benzothiazol-2-yl) (4-fluoro-5- (tetrahydro-3-oxo-1H, 3H- [1,3,4] thiadiazolo- [3,4 yl) -amino] -phenyl] -thio-acetate (fluthiasset-methyl), 5- (2- (4-trifluoromethyl-phenoxy) -N-methylsulfonyl-2-nitro-benzamide (pomesafen), 2 - [[[[(4,6- dimethoxy-2-pyrimidinyl) (2-amino-4- (hydroxymethylphosphinyl) - < / RTI > (R) -2- [4- (3-Chloro-pyrimidin-2-yl) -pyrrolidinecarboxylic acid (ammonium salt) (glyphosinate- (ammonium) (Methyl ester, 2-ethoxy-ethyl ester, butyl ester) (Haloxyfop, -methyl, -P-methyl, 3-cyclohexyl-6-dimethylamino-1-methyl-1,3,5-triazine-2,4 (1H, 3H) -dione (hexaquinone), methyl 2- (Imazametabenz-methyl), 2- (4-methyl-4-methyl-benzothiazol- , 5-dihydro-4-methyl-4- Methyl-pyridine-3-carboxylic acid (imazametaphyr), 2- (4,5-dihydro-4-methyl- Imidazol-2-yl) -5-methoxymethyl-pyridine-3-carboxylic acid (imazamox), 2- (4,5-dihydro- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-quinolin- (2-chloro-4-methoxy-pyrimidin-2-yl) -N- (Imazosulfuron), N- (4-methoxy-6-methyl-1,3,5-triazine-2 - iodo-2-methoxycarbonyl-phenylsulfonyl) -urea sodium salt (iodosulfuron-methyl-sodium), 4-hydroxy-3,5-diiodo (1-ethyl-1-methyl-propyl) -benzonitrile (ioxynil), N, N-dimethyl- -Isoxazol-5-yl) -2,6- (5-cyclohexyl-phenyl) - (5-cyclopropyl-isoxazol-4-yl) methanone (isoxaprochlor), (5-cyclohexyl- (Isoxafluoro-propyl-isoxazol-4-yl) - (2- methylsulfonyl-4- trifluoromethyl- (2-ethoxy-1-methyl-2-oxo-ethyl) - isoquinolin- N, N '- (3,4-Dichloro-phenyl) -N-methoxy-N-methyl-lH-pyrazole (2-methyl-phenoxy) -propionic acid (methoproteine), 2- (4-chloro-2-methyl- (2-benzothiazolyloxy) -N-methyl-N-phenyl- acetamide (mepenacet), methyl 2 - [[[[(4,6- dimethoxy-2- pyrimidinyl) amino] carbonyl] Amino] sulfonyl] -4- [[(methylsulfonyl) amino] methyl] -benzoate (methosulfuron) Amino-3-methyl-6-phenyl-l, 2,4-triazine-5 (4H) -one (Methaetron), N ' - (4- (2-chloro-phenyl) Dihydro-2-methoxy-2,4,4-trimethyl-2H- 1 -benzopyran-7-yl-oxy) -phenyl) -N-methoxy- (2-ethyl-6-methyl-phenyl) -N'- (4-bromophenyl) -N-methoxy-N-methylurea (methobromorone) ) - N- (2-methoxy-1-methyl-ethyl) -acetamide (metolachlor, S-metolachlor) (3-chloro-4-methoxy-phenyl) -N- (4-methoxy-phenyl) (4-amino-6-t-butyl-3-methylthio-1,2,4-triazine-5 (4H) Methoxy-6-methyl-1,3,5-triazin-2-yl) -N '-( 2- methoxycarbonyl- phenylsulfonyl ) - urea (methsulfuron-methyl), S-ethyl-hexahydro-1H-azepine-1 -carbothioate (molinate), 2- (2-naphthyloxy) N- (4,6-dimethoxy-pyrimidin-2-yl) - (4-methoxyphenyl) -N-methyl-urea (3-dimethylcarbamoyl-pyridin-2-yl-sulfonyl) -urea (nicosulfuron), 4-chloro-5-methylamino- (2H) -pyridazinone (Norflurazone), S- (2-chloro-benzyl) -N, N-diethyl-thiocarbamate (ObenCab), 4-dipropylamino- (2-propynyloxy) -phenyl] -5- (t-butyl) -1,3,4-oxadiazole-2 (3H) -one (oxadiaryl), 3- [2,4-dichloro-5- (1-methyl-ethoxy) -phenyl] (2-oxetan-3-yl-oxycarbonyl-phenyl) -pyridin-2 (3H) Sulfonyl) -urea (< / RTI > oxazepuron) , 3- [1- (3,5-dichloro-phenyl) -l-propyl] -2,3-dihydro-6-methyl- 4-nitro-phenoxy) -4-trifluoromethylbenzene (oxyfluorfen), 1,1'-dimethyl-4,4 (Bipyridinium) (para-artificial), 1-amino-N- (1-ethyl-propyl) -3,4- Amino-3,5,6-trichloro-pyridine-2-carboxylic acid (picloram), 2-methyl- (Picolinafen), 2-chloro-N- (2,6-difluoro-phenyl) Diethyl-phenyl) -N- (2-propoxy-ethyl) -acetamide (pretilachlor), N- (4,6-bisdifluoromethoxy-pyrimidin- Chloro-4-fluoro-5 - [(6S, 7aR) -6-fluoro < / RTI > Tetrahydro-1,3-dioxo (2-chloro-N-isopropyl-N-phenyl-acetamide) was prepared in accordance with the general method of example 1 from 2- (Propyl), (R) - [2 - [[(1-methylethylidene) amino] -oxy] -ethyl] 2-chloro-N- (2-ethyl-6-methyl-phenyl) -propan- Methyl 2 - [[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1 H S-phenylmethyl N, N-dipropyl-benzoate sodium salt (propoxycarbazone-sodium), S- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2- (3,3,3-trifluoro (4-chloro-5-difluoromethoxy-l-methyl-lH-pyrazol-3-yl) -propyl) -phenylsulfonyl) -urea (prosulfuron) 4-flu 5-a] pyridin-2-yl) -5 (trifluoromethyl) -5-oxo- - (methyl-2-propynylamino) -1H-pyrazole-4-carbonitrile (pyrazolidyl), 4- (2,4- (Phenylsulfonyloxy) -pyrazole (pyrazolate), 4- (2,4-dichloro-benzoyl) -l, 3- dimethyl- 5- (phenylcarbonyl- methoxy) ), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '-( 4- ethoxycarbonyl- Furon-ethyl), O- [2,6-bis- (4,6-dimethoxy-pyrimidin- Phenyl-4-pyridazinol (pyridapol), O- (6-chloro-3-phenyl-pyridazin- Pyridazin-4-ol (pyridato), 7 - [(4,6-dimethoxy-2-pyrimidinyl) -thio] -3-methyl-1 (3H) -isobenzofuranone ), Me (2-chloro-6- (4,6-dimethoxy-pyrimidin-2-yl) Chloroquinoline-8-carboxylic acid (quinomelac), 2, 3-dichloro-quinoline-8-carboxylic acid (quinclorac) (Ethyl ester, tetrahydro-2-furanyl-methyl ester) (quizalofopro, -ethyl, -P-ethyl , -P-terfuryl), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (3-ethylsulfonyl-pyridin- ), 2- (1-ethoximinobutyl) -5- (2-ethylthiopropyl) -3-hydroxy-2-cyclohexen-1-one (cetoxydim) 2-chloro-4-methyl-sulfonyl-benzoyl) -cyclohexane-1,3-dione (sulcotrione), 2 - (2,4-Dichloro-5-methyl-sulfonylamino-phenyl) -4-difluoromethyl-5-methyl- (2-methyl-2 - [[[[(4,6-dimethyl-2-pyrimidinyl) amino] carbonyl] amino] sulfo (4-trifluoromethyl-phenyl) -benzoate (sulfomethuron-methyl), N-phosphonomethyl-glycine-trimethylsulfonium (sulfosate) (2-ethylsulfonyl) -imidazo [1,2-a] pyridine-3-sulfonamide (sulfosulfuron), 6-chloro-4-ethylamino- -Triazine (terbutaline), 2-t-butylamino-4-ethylamino-6-methylthio-1,3,5-triazine (terbutaline) (4-methoxy-2-thienyl-methyl) -acetamide (decyl chloride), methyl 2-difluoromethyl-5- 6-dimethyl-3H-pyrazole-3-carboxylate (thiazopyr), 6- (6,7-dihydro- Pyrrolo [2,1-c] -1,2,4-thiadiazol-3-ylideneamino) -7-fluoro-4- (2- Benzoyl-3 (4H) - (Thiadiazine), N- (4-methoxy-6-methyl-1,3,5-triazin- Methyl-2- (ethoximino-propyl) -3-hydroxy-5- (2,4,6-trimethyl-phenyl) -2-cyclohexen- (Tricalocoxydim), S- (2,3,3-trichloro-2-propenyl) diisopropylcarbamothioate (triallyl), N- (4-methoxy- , N-methyl-N- (4-methoxy-benzenesulfonyl) Methyl-1,3,5-triazin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) -urea (Tribenuron- (Trichloropyr), 2- (3,5-dichloro-phenyl) -2- (2,2,2-trichloro-ethyl) oxirane (2, 2, 2-trifluoro-ethoxy) -2-pyridinecarbonyl] Amide sodium salt (triple-lock facility furon), 1-amino-2,6- N, N-dipropyl-4-trifluoromethyl-benzene (trifluralin), N- [4-dimethylamino-6- (2,2,2-trifluoro-ethoxy- , 5-triazin-2-yl] -N '- (2-methoxycarbonyl-phenylsulfonyl) -urea (triflusulfuron- N, N ' - [(4,6-dimethoxy-phenyl) (WO-A-92/10660), 4- [4, 5-dimethoxy- 2 - [(ethylsulfonyl) amino] -5-methyl-5-oxo-3- (&Quot; active compound of group 2 ") selected from the second group of herbicides comprising the active compound of formula (I)
[8] (c) Synthesis of 4-dichloroacetyl-1-oxa-4-aza-spiro [4.5] -decane (AD-67), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo [ a] -pyrimidin-6 (2H) -one (BAS-145138), 4-dichloroacetyl-3,4-dihydro- Methyl-hexyl 5-chloro-quinoxaline-8-oxy-acetate (cloquintocet-mexyl), a- (cyano-methoximino) -phenylacetonitrile (siomethynyl), 2,4- (2-propenyl) -acetamide (2,4-D), 2,2-dichloro-N- (2- -24), 2,2-dichloro-N, N-di-2-propenyl-acetamide (dichloride), N- Dichloro-2-phenyl-pyrimidine (pancylim), ethyl 1- (2,4-dichloro-phenyl) -5-trichloromethyl-1H- 2,4-triazole-3-carboxylate (pancolazol-ethyl), phenylmethyl 2-chloro-4-trifluoromethyl- 3-dioxolan-2-yl-methoxy) - alpha -trifluoro-acetophenone oxime (Fluxophenem), 3-chloro-N- (Furilazole, MON-13900), ethyl 4,5-dihydro-5,5-diphenyl-3-yne (4-chloro-2-methylphenoxy) -acetic acid (MCPA), (+) 2- (4-chloro-2-methylphenoxy) propanoic acid Dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), 2- (MG-191), 1,8-naphthalic anhydride, - (1,3-dioxolan-2-ylmethoximino) -phenylacetonitrile 2-yl-methyl) -N- (2-propenyl) -acetamide (PPG-1292), 3-dichloroacetyl -2,2,5-trimethyl-oxazolidine (R-29148), N-cyclopropyl-4 - [[(2-methoxy- -Amino] -sulfonyl] -benzamide (WO-A-99/66795), N - [(4- methoxyacetylamino) -phenyl] -sulfonyl-2-methoxy- A-99/66795) and at least one crop selected from the group of N - [(4-methylaminocarbonylamino) -phenyl] -sulfonyl-2-methoxy- An effective amount of an active compound comprising an effective amount of a compound of the formula:
[9]
[10] In this formula,
[11] R ¹ represents hydrogen, amino or, optionally, cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted alkyl of 1 to 5 carbon atoms,
[12] R < ^{2 >} is optionally halogen-substituted alkyl of 1 to 5 carbon atoms,
[13] R ³ represents hydrogen, halogen, or optionally halogen-substituted alkyl of 1 to 5 carbon atoms,
[14] R ⁴ represents hydrogen, cyano or halogen,
[15] R ⁵ represents cyano, thiocarbamoyl or halogen,
[16] R ⁶ represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, hydroxyl, mercapto, amino, hydroxyamino, aminosulfonyl or halogen, or in each case not more than 6 carbon atoms, the optionally cyano-, hydroxyl -, C ₁ -C ₄ - alkoxy -, C ₁ -C ₄ - alkylcarbonylamino -, C ₁ -C ₄ - alkoxycarbonyl -, C ₂ -C ₄ - alkenyloxy (C ₁ -C ₄ -alkyl) -aminocarbonyl-, C ₂ -C ₄ -alkynyloxycarbonyl-, C ₁ -C ₄ -alkylaminocarbonyl-, di- (C ₁ -C ₄ -alkyl) -aminocarbonyl-, phenoxycarbonyl - and / or phenylaminocarbonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl or alkylamino, or having in each case not more than 6 carbon atoms in each case optionally cyano-, carboxyl-, halogen- and / or C ₁ -C ₄ - alkoxycarbonyl-substituted alkenyl, alkynyl, alkenyloxy or alkynyloxy or indicate, If those having 6 or fewer carbon atoms in the alkyl group in each case optionally halogen-or C ₁ -C ₄ - alkoxy-substituted alkylcarbonyl-amino, alkoxycarbonylamino, amino, alkylsulfonyl amino, N, N- bis - Alkylsulfonylamino or N-alkylcarbonyl-N-alkylsulfonylamino, or in each case alkyl groups having up to 6 carbon atoms and in each case by cyano or by halogen, or by C ₁ -C ₄ C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkoxycarbonyl which in each case is C ₁ -C ₄ -alkoxycarbonyl, C ₃ -C ₄ -alkenyloxycarbonyl or C ₃ -C ₄ -alkoxycarbonyl, Phenylcarbonyl-N-alkylsulfonylamino, N-pyridylcarbonyl-N-alkylsulfonylamino optionally substituted by C _1-4 -alkynyloxycarbonyl, N-furylcarbonyl-N-alkylsulfonylamino or N-thienylcarbonyl-N-alkylsulfonylamino.
[17] Preferred meanings of the radicals represented by the above general formula (I) are as follows:
[18] R ¹ preferably represents hydrogen, amino or in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl or n or i-
[19] R ² preferably represents in each case optionally fluorine- and / or chlorine-substituted methyl, ethyl or n or i-propyl,
[20] R ³ is preferably hydrogen, fluorine, chlorine, bromine or in each case optionally fluorine- and / or chlorine-substituted methyl, ethyl or n or i-
[21] R ⁴ preferably represents hydrogen, cyano, fluorine, chlorine or bromine,
[22] R ⁵ preferably represents cyano, thiocarbamoyl, fluorine, chlorine or bromine,
[23] R ⁶ represents preferably nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, hydroxyl, mercapto, amino, hydroxyamino, aminosulfonyl, fluorine, chlorine or bromine, Or alkoxycarbonyl-, methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, Ethyl, n- or i-propyl, n-, i- or s-propoxycarbonyl-, n- or i-propoxycarbonyl-, allyloxycarbonyl- or propargyloxycarbonyl- Butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, methylthio, ethylthio, n- or i- Thio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i- Methylamino, ethylamino , n- or i-propylamino, or n-, i- or s-butylamino, or in each case optionally cyano-, carboxyl-, fluorine-, chlorine-, bromine-, methoxycarbonyl- and Or ethoxycarbonyl-substituted ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy or butynyloxy, Substituted or unsubstituted alkyl, alkoxy, fluorine- and / or chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, N- or i-propylcarbonylamino, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t-butylsulfonyl Amino, N, N-bis-methylsulfonylamino, N, N-bis-ethylsulfonylamino, N-ethylsulfonyl-N-methylsulfonylamino, N-methylsulfonyl- , N-methylsulfonyl-N-propylsulfonylamino, N-acetyl-N-methylsulfonylamino, N-propionyl- Butyryl-N-methylsulfonylamino, N-butylamino-N-methylsulfonylamino, N-butylamino- ) -N-ethylsulfonylamino, N- (2-methylpropanoyl) -N-ethylsulfonylamino, N-acetyl- N-butyroyl-N-ethylsulfonylamino, N-butyroyl-N-ethylsulfonylamino or Nt-butyroyl- Amino, or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t- Trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted N-phenylcarbonyl-N-methylsulfonylamino, N-phenylcarbonyl-N-ethylsulfonylamino, N-thienylcarbonyl-N-methylsulfonylamino or N-thienylcarbonyl- ≪ / RTI >
[24] R < ¹ > particularly preferably represents hydrogen, amino, methyl or ethyl,
[25] R ² particularly preferably represents in each case fluorine- and / or chlorine-substituted methyl or ethyl,
[26] R ³ particularly preferably represents hydrogen, fluorine, chlorine, bromine or in each case optionally fluorine- and / or chlorine-substituted methyl or ethyl,
[27] R ⁴ particularly preferably represents hydrogen, fluorine or chlorine,
[28] R < ⁵ > particularly preferably represents cyano, thiocarbamoyl, chlorine or bromine,
[29] R ⁶ particularly preferably represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, hydroxyl, mercapto, amino, hydroxyamino, aminosulfonyl, fluorine, chlorine or bromine, Or methoxycarbonyl-, n-or i-propoxycarbonyl-, methoxy-, ethoxy-, acetyl-, propionyl-, methoxycarbonyl- and / or ethoxycarbonyl-, Methyl, ethyl, n-or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propyloxycarbonyl- or propargyloxycarbonyl- Ethoxycarbonyl, n- or i-propyl, such as methoxycarbonyl, ethoxycarbonyl, ethoxycarbonyl, propylthio, propylthio, methylsulfinyl, ethylsulfinyl, Methyl, ethyl, amino or n- or i-propylamino, or in each case optionally cyano-, carboxyl-, fluorine-, Propynyl, propenyloxy or propynyloxy, or in each case optionally fluorine-, bromine-, methoxycarbonyl- and / or ethoxycarbonyl-substituted ethenyl, propenyl, ethynyl, And / or one or more substituents selected from chlorine-, methoxy- or ethoxy-substituted acetylamino, propionylamino, methoxycarbonylamino, ethoxycarbonylamino, methylsulfonylamino, ethylsulfonylamino, n- or i- Sulfonylamino, n-, i-, s- or t-butylsulfonylamino, N, N-bis-methylsulfonylamino, N, N- Methylsulfonylamino, N-methylsulfonylamino-N-propylsulfonylamino, N-acetyl-N-methylsulfonylamino, N-propionyl- N- (2-methylpropanoyl) -N-ethylsulfonylamino, Nn-butyroyl-N- Methylsulfonylamino, Ni-Bu N-methylsulfonylamino, N-acetyl-N-ethylsulfonylamino, N-propylsulfonylamino, N-ethylsulfonylamino, N-butyroyl-N-ethylsulfonylamino, Nt-butylsulfonylamino, Nt- Methyl-ethyl, trifluoromethyl-, methoxy-, ethoxy-, isopropoxy-, butyro-N-ethylsulfonylamino, or in each case optionally cyano-, fluorine-, chlorine-, bromine-, , Difluoromethoxy- or trifluoromethoxy-substituted N-phenylcarbonyl-N-methylsulfonylamino, N-phenylcarbonyl-N-ethylsulfonylamino, N-thienylcarbonyl- Sulfonylamino or N-thienylcarbonyl-N-ethylsulfonylamino.
[30] Very particularly preferred components of the active formulations according to the invention are < RTI ID = 0.0 >
[31] R < ¹ > represents amino,
[32] R ² represents trifluoromethyl,
[33] R ³ represents hydrogen, chlorine or methyl,
[34] R ⁴ represents fluorine,
[35] R < ⁵ > represents cyano or thiocarbamoyl,
[36] R ⁶ is in each case optionally fluorine- and / or chlorine-substituted methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t- Amino, N, N-bis-methylsulfonylamino, N, N-bis-ethylsulfonylamino, N-ethylsulfonyl-N-methylsulfonylamino, N-methylsulfonyl- N-methylsulfonylamino, N-acetyl-N-methylsulfonylamino, N- (2,2-dimethylpropanoyl) -N -N-ethylsulfonylamino, N- (2-methylpropanoyl) -N-ethylsulfonylamino, N, N-butyroyl- Methylsulfonylamino, N-methoxyacetyl-N-methylsulfonylamino, N-acetyl-N-ethylsulfonylamino, N- Propionyl-N-ethylsulfonylamino, N-butyroyl-N-ethylsulfonylamino, Ni-butyroyl N-ethylsulfonylamino, N-methoxyacetyl-N-ethylsulfonylamino, N-methoxyacetyl-N-ethylsulfonylamino, In each case optionally substituted with one or more substituents selected from the group consisting of cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- or trifluoromethoxy- N-phenylcarbonyl-N-methylsulfonylamino, N-phenylcarbonyl-N-ethylsulfonylamino, N-thienylcarbonyl-N-methylsulfonylamino or N-thienylcarbonyl- (I) < / RTI >
[37] Other very particularly preferred components of the active formulations according to the invention are
[38] R < ¹ > represents methyl,
[39] R ² represents trifluoromethyl,
[40] R ³ represents hydrogen, chlorine or methyl,
[41] R ⁴ represents fluorine,
[42] R ⁵ represents thiocarbamoyl,
[43] R ⁶ is in each case optionally fluorine- and / or chlorine-substituted methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t- Amino, N, N-bis-methylsulfonylamino, N, N-bis-ethylsulfonylamino, N-ethylsulfonyl-N-methylsulfonylamino, N-methylsulfonyl- N-methylsulfonylamino, N-acetyl-N-methylsulfonylamino, N- (2,2-dimethylpropanoyl) -N -N-ethylsulfonylamino, N- (2-methylpropanoyl) -N-ethylsulfonylamino, N, N-butyroyl- Methylsulfonylamino, N-methoxyacetyl-N-methylsulfonylamino, N-acetyl-N-ethylsulfonylamino, N- Propionyl-N-ethylsulfonylamino, N-butyroyl-N-ethylsulfonylamino, Ni-butyroyl N-ethylsulfonylamino, N-methoxyacetyl-N-ethylsulfonylamino, N-methoxyacetyl-N-ethylsulfonylamino, In each case optionally substituted with one or more substituents selected from the group consisting of cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- or trifluoromethoxy- N-phenylcarbonyl-N-methylsulfonylamino, N-phenylcarbonyl-N-ethylsulfonylamino, N-thienylcarbonyl-N-methylsulfonylamino or N-thienylcarbonyl- (I) < / RTI >
[44] Yet another very particularly preferred component of the active formulations according to the invention is
[45] R < ¹ > represents amino or methyl,
[46] R ² represents trifluoromethyl,
[47] R ³ represents hydrogen, chlorine or methyl,
[48] R ⁴ represents hydrogen, fluorine or chlorine,
[49] R < ⁵ > represents cyano, thiocarbamoyl or chlorine,
[50] R ⁶ represents a carboxyl, carbamoyl, thiocarbamoyl, hydroxyl, mercapto, amino, fluorine, chlorine or bromine or in each case optionally cyano-, carboxyl-, hydroxyl-, methoxy-, ethoxy -, acetyl-, propionyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, allyloxycarbonyl- or propargyloxycarbonyl-substituted methyl, ethyl, n-or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, N-propyl, n-propyl, n-propyl, n-butoxy, n-butoxy, - (2,2-dimethylpropanoyl) -N-ethylsulfonylamino or N- (2-methylpropanoyl) -N-ethylsulfonylamino, or in each case optionally cyano-, -, fluorine-, chlorine-, bromine-, methoxycarbonyl- and / or ethoxycarbonyl-substituted ethenyl, propenyl, ethynyl, propynyl, propenyloxy or propynyloxy I).
[51] As examples of compounds of the general formula (I) which can be used as a mixing partner according to the present invention, the following compounds may be mentioned:
[52] 4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) -pyrimidinyl) -2-methoxy-benzonitrile ,
[53] 4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) -pyrimidinyl) -2-ethoxy-benzonitrile ,
[54] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-n-propoxy- Benzonitrile,
[55] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-i-propoxy- Benzonitrile,
[56] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-n-butoxy- Benzonitrile,
[57] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-i-butoxy- Benzonitrile,
[58] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-s-butoxy- Benzonitrile,
[59] 4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-l (2H) -pyrimidinyl) -2-allyloxy-benzonitrile ,
[60] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-propargyloxy-benzo Nitrile,
[61] (2H) -pyrimidinyl) -2 - [(1-methyl < RTI ID = 0.0 & -2-propynyl) -oxy] -benzonitrile,
[62] Methyl 2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l (2H) -pyrimidinyl)
[63] Ethyl 2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l (2H) -pyrimidinyl)
[64] chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinyl)
[65] i-propyl 2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4- trifluoromethyl- 1 (2H) -pyrimidinyl)
[66] 2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4- -Trifluoromethyl-1 (2H) -pyrimidinyl) -benzoate, < / RTI >
[67] 2- (Methylsulfonylamino) -5- fluoro-4- [3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro- 1 (2H) -pyrimidinyl ] -Benzene < / RTI > carbothioamide,
[68] 2- (Ethylsulfonylamino) -5- fluoro-4- [3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro- 1 (2H) -pyrimidinyl ] -Benzene < / RTI > carbothioamide,
[69] 2- (n-propylsulfonylamino) -5-fluoro-4- [3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro- ≪ RTI ID = 0.0 > midenyl] -benzenecarbothioamide,
[70] Synthesis of 2- (i-propylsulfonylamino) -5-fluoro-4- [3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro- ≪ RTI ID = 0.0 > midenyl] -benzenecarbothioamide,
[71] 2- (n-Butylsulfonylamino) -5-fluoro-4- [3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro- ≪ RTI ID = 0.0 > midenyl] -benzenecarbothioamide,
[72] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- -Phenyl] -N- (acetyl) -1-methanesulfonamide,
[73] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- - phenyl] -N- (methylsulfonyl) -1-methanesulfonamide,
[74] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- - phenyl] -N- (ethylsulfonyl) -1-methanesulfonamide,
[75] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- -Phenyl] -N- (ethylsulfonyl) -1-ethanesulfonamide,
[76] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- -Phenyl] -N- (n-propylsulfonyl) -1-methanesulfonamide,
[77] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- -Phenyl] -N- (i-propylsulfonyl) -1-methanesulfonamide,
[78] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- -Phenyl] -N- (acetyl) -1-methanesulfonamide,
[79] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- -Phenyl] -N- (acetyl) -1-ethanesulfonamide,
[80] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- -Phenyl] -N- (propanoyl) -1-methanesulfonamide,
[81] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- -Phenyl] -N- (propanoyl) -1-ethanesulfonamide,
[82] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- -Phenyl] -N- (2-methylpropanoyl) -1-methanesulfonamide,
[83] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- -Phenyl] -N- (2-methylpropanoyl) -1-ethanesulfonamide,
[84] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- - phenyl] -N- (butanoyl) -1-methanesulfonamide,
[85] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- -Phenyl] -N- (butanoyl) -1-ethanesulfonamide,
[86] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- -Phenyl] -N- (2-methylbutanoyl) -1-methanesulfonamide,
[87] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- -Phenyl] -N- (2-methylbutanoyl) -1-ethanesulfonamide,
[88] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- -Phenyl] -N- (2,2-dimethylpropanoyl) -1-methanesulfonamide,
[89] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- -Phenyl] -N- (2,2-dimethylpropanoyl) -1-ethanesulfonamide,
[90] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- -Phenyl] -N- (methoxyacetyl) -1-methanesulfonamide,
[91] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- -Phenyl] -N- (methoxyacetyl) -1-ethanesulfonamide,
[92] 4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- -Phenyl] -N- (methoxybenzoyl) -1-ethanesulfonamide,
[93] Dihydro-1 (2H) -pyrimidinyl) -2-cyano-4-fluoro < / RTI > -Phenyl] -N-benzoyl-1-methanesulfonamide,
[94] Dihydro-1 (2H) -pyrimidinyl) -2-cyano-4-fluoro < / RTI > -Phenyl] -N-benzoyl-1-ethanesulfonamide,
[95] Dihydro-1 (2H) -pyrimidinyl) -2-cyano-4-fluoro < / RTI > - phenyl] -N- (4-methoxybenzoyl) -1-methanesulfonamide,
[96] Dihydro-1 (2H) -pyrimidinyl) -2-cyano-4-fluoro < / RTI > -Phenyl] -N- (2-thienylcarbonyl) -1-methanesulfonamide,
[97] Dihydro-1 (2H) -pyrimidinyl) -2-cyano-4-fluoro < / RTI > -Phenyl] -N- (2-thienylcarbonyl) -1-ethanesulfonamide.
[98] Compound [1,1-dimethyl-2-oxo-2- (2-propenyloxy)] - ethyl 2-Chloro-5- (3,6-dihydro- (I-1) - CAS-Reg.No .: 134605-64-4 - is particularly emphasized as a mixed component of the general formula (I) (See WO 91/00278).
[99] Similarly, the compound 5-fluoro-4- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) 1-methyl-2-propynyl) oxy] -benzonitrile (I-2) - CAS -Reg.No .: 186605-50-5- is particularly emphasized as a mixed component of the general formula (I) WO 97/01541).
[100] Also according to CA (Chemical Abstracts), N- [2-cyano-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl- Phenyl] -N-ethylsulfonyl-2,2-dimethylpropanamide (CAS Reg.No .: 232262-67-8) which is also referred to as N- [2-cyanopyridine (2H) -pyrimidinyl) - phenyl] -N- (4-fluoro-pyridin-2-yl) (2,2-dimethylpropanoyl) -1-ethanesulfonamide (I-3) is particularly emphasized as a mixed component of the general formula (I) (WO 95/29168).
[101] Also, according to CA, a mixture of N- [2-cyano-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1- (2H) -pyrimidinyl) -4-fluoro-phenyl] -N-ethylsulfonyl-4-methoxy-benzamide (CAS Reg. No. 184293-08-1) Trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -phenyl] -N- (4-methoxyphenyl) (I-4) is particularly emphasized as a mixed component of the general formula (I) (see WO 96/35679).
[102] Also, according to CA, a mixture of N- [2-cyano-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1- (2H) -pyrimidinyl) Trifluoro-phenyl] -N-ethylsulfonyl-2-thiophene-carboxamide, N- [5- (3- (2H) -pyrimidinyl) -2-cyano-4-fluoro-phenyl] -N- (2-thienylcarbonyl) -1- ethanesulfonamide I-5) is particularly emphasized as a mixed component of the general formula (I) (WO 96/35679).
[103] Further, according to CA, 4- (3,6-dihydro-3-methyl-2,6-dioxo-4- trifluoromethyl- 1 (2H) -pyrimidinyl) -2- ethylsulfonylamino (Ethylsulfonylamino) -5-fluoro-4- [3-methyl-2 (trifluoromethyl) phenyl) -5-fluoro-benzenethiocarbamoide (CAS Reg.No .: 173980-09-1) 6-dioxo-4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl] -benzenecarbothioamide (I- (WO 95/30661).
[104] The compounds of formula (I) are described in the above-mentioned patent applications or patents as N-aryl-uracil.
[105] Depending on the chemical structure, the active compounds of group 2 can be classified into the following classes of active compounds:
[106] Amides such as isoxan, picolinafen, propanil, arylheterocycles such as azaphenidine, benzpendizone, butapenacyl-allyl, carpentrazone-ethyl, Ethyl, pyridate, pyridapol, sulphite, pyruvate, pyruvate, pyruvate, pyruvate, pyruvate, pyruvate, pyruvate, L, 4-triazol-1-yl] -2 (3-trifluoromethyl) - (2-ethylsulfonyl) amino] -5-fluoro-benzenecarbothioamide), aryloxyphenoxypropionate (for example clodipafoip-propargyl, cyhalofop- Methyl, quizalofopop-P-ethyl), carboxylic acid derivatives (for example, clopyralid, dicamba, Fluclofir, picloram, trichlorophyl) , Benzothiadiazole (for example, benzazone), chloroacetamide (for example, acetochlorine, alachlor, butachlor, (S-) dimethenamide, metazachlor, metolachlor, (For example, benzofurans, fenchloride, propycochlor), cyclohexanedione (for example, butloxydim, clexoxydim, cycloxydim, cetoxydim, tricalcoxim), dinitroaniline (For example, lauryl, dirzalin, pendimethalin, trifluralin), diphenyl ethers (such as acifluorfen-sodium, aclonifene, bifenox, fluoroglycopen-ethyl, pomesapen, lactophen, oxyfluorfen ), Imidazolinone (for example imazametabenz-methyl, imazamox, imazapyr), urea (e.g., chlorotoluron, diuron, isoproturon, Zaccine, Imazetapyr), isoxazole (for example isoxaflutol), nicotine Such as, for example, nitril (e.g. diflifenacin), nitrile (e.g. bromocinninyl, dioxinyl), organophosphorus compounds (such as glucosylphosphonate, ammonium glyphosate, ), Oxyacetamides (e.g., flupenase, mefenacet), phenoxycarboxylic acid derivatives (e.g., 2,4-D, dichlorpropop-P, MCPA, MCPB, (E.g., dithiopyr, thiazopyr), pyrimidinyl (thio) benzoate (e.g., pyrazolidine, pyrazolidine), pyridazinone (Such as bispyrimidine, pyrimidine, pyrimidine, pyrimidine, pyrimidine, pyrimidine, pyrimidine, pyrimidine, Sulforrone, cyclosulfamuron, ethoxylated furon, flupyrsulfuron-methyl-sodium, porlamysulfuron, iodosulfuron-methyl-sodium, Methylsulfuron, methylsulfuron-methyl, sulfosulfuron-methyl, sulfosulfuron-methyl, sulfosulfuron-methyl, (E.g. pentylamid), thiocarbamates (e.g., butyrate, butyrate, and the like) such as methyl, triisulfuron, (Such as amethrin, atrazine, cyanazine, dimelipram, simajin, terbutyl azine, isopropyl myristate, isopropyl myristate, (For example, aminocarbazone, flucarbazone-sodium, pro-aminobutyric acid), triazinone (for example, Sodium, potassium), triazolopyrimidine (e.g., chloranesulam-methyl, dichlo Ram, Flora seolram, fluorenyl meth seolram, methoxy toseol Ram), tri ketones (e. G. Meso-on tree, snow coat Leone), uracil (e. G. Bromo drink).
[107] Of the active compounds of group 2, the following compounds can be particularly emphasized as mixed components:
[108] But are not limited to, acetonitrile, acetonitrile, acetonitrile, acetonitrile, acetonitrile, acetonitrile, acetonitrile, acetonitrile, But are not limited to, methanamide, diuron, EPTC, fenoxaprop-P-ethyl, pentrazamid, flucarbazone-sodium, flupenase, flumetsulam, glufosinate-ammonium, glyphosate-isopropylammonium, But are not limited to, but are not limited to, chymotrypsin, imazacin, imazetapyr, isoxaflutol, mesotrione, metolachlor, S-metolachlor, methosulam, metribuzin, nicosulfuron, Sulfoxyl-methyl, trifluralin, 4- [4, 5-dimethyl-1, 2, 3, Methyl-5-oxo- (3-trifluoromethyl-1H-1,2,4-triazol- 1 -yl] -2 - [(ethylsulfonyl) amino] -Benzene carbonyl thioamide.
[109] Depending on the chemical structure, the particularly emphasized active compounds of group 2 can be classified as active compounds of the following classes:
[110] Dihydro-4-methyl-5-oxo- (3-trifluoromethyl-1H-1,2,4) -carbamic acid tert- 2-yl] -2-f (ethylsulfonyl) amino] -5-fluoro-benzenecarbothioamide), chloroacetamide (for example acetochlorine, alachlor, dimethenamid, S- (E.g., dimethanamide, metolachlor, S-metolachlor), dinitroaniline (e.g., pendimethalin, triflualin), urea (e. G. Diuron), imidazolinone (For example, sulfamethoxazole, imazatapyr, imazethapyr), organophosphorus compounds (for example, glucoside, glyphosate, sulfosate), oxyacetamide (for example flupenase), pyridazinone Lysine), sulfonylureas (e.g. chlorimuron-ethyl, nicosulfuron, limsulfuron, sulfomethuron-methyl, (Eg, atrazine, cyanazine, simajin, tbutyl azine), triazinone (eg, methotribazine), triazolinone (eg, amikabazone, flucarbazone- (E.g., propoxycarbazone-sodium), triazolopyrimidines (e.g., diclosulam, florasulam, methosulam), triketones (such as mesotrione, sulcotrione), uracil ).
[111] The composition according to the invention may comprise one or two active compounds of group 1 and one active compound of group 3.
[112] The compositions according to the invention preferably comprise one or two active compounds of group 1, active compounds of one to three groups 2 and optionally one group 3 of active compound.
[113] In particular, the composition according to the invention comprises one group 1 of active compounds, one or two of group 2 of active compounds and optionally one of group 3 of active compounds.
[114] In each case, one active compound of group 1 and two active compounds of group 2 (preferably selected from the group of photosynthesis inhibitors and, on the other hand, from the group of acetyl-CoA-carboxylase inhibitors) or in each case one group Examples of combinations according to the invention comprising the active compound of 1, the active compounds of two groups 2 and the active compound of one group 3 are listed in Table 1 below.
[115] Table 1
[116]
[117] Table 1 - Continued
[118]
[119] Table 1 - Continued
[120]
[121] Table 1 - Continued
[122]
[123] Table 1 - Continued
[124]
[125] Table 1 - Continued
[126]
[127] Table 1 - Continued
[128]
[129] Table 1 - Continued
[130]
[131] Table 1 - Continued
[132]
[133] Table 1 - Continued
[134]
[135] Table 1 - Continued
[136]
[137] Table 1 - Continued
[138]
[139] Table 1 - Continued
[140]
[141] Table 1 - Continued
[142]
[143] Table 1 - Continued
[144]
[145] Table 1 - Continued
[146]
[147] Table 1 - Continued
[148]
[149] Table 1 - Continued
[150]
[151] Further examples of combinations according to the invention comprising one active compound of group 1 and one or two active compounds of group 2 and / or one active compound of group 3 in each case are listed in table 2 below.
[152] Table 2
[153]
[154] Table 2 - Continued
[155]
[156] Table 2 - Continued
[157]
[158] Table 2 - Continued
[159]
[160] Table 2 - Continued
[161]
[162] Table 2 - Continued
[163]
[164] Table 2 - Continued
[165]
[166] Table 2 - Continued
[167]
[168] Table 2 - Continued
[169]
[170] Table 2 - Continued
[171]
[172] Table 2 - Continued
[173]
[174] Table 2 - Continued
[175]
[176] Surprisingly, in accordance with the present invention, the above-defined active combinations of the above-mentioned active compounds of Group 2 with N-aryl-uracil of the general formula (I) exhibit not only excellent crop compatibility but also excellent herbicidal activity , It has been found that it can be selectively used to control monocotyledonous and dicotyledonous weeds in various crops, especially cereals, such as wheat, barley or oats and corn, and also to control monocotyledonous and dicotyledonous weeds in semi-and non-selective areas . Also, the effect is particularly good in corn.
[177] Surprisingly, the herbicidal effect of the active compounds according to the invention of the abovementioned compounds of groups 1 and 2 overcomes the total action of the individual active compounds.
[178] Thus, there is an unexpected synergy that is not complementary. The new active formulations are tolerant to a large number of crops and can effectively control weeds which are usually difficult to control. Thus, the novel active compounds are more useful as herbicides.
[179] The synergistic effect of the active formulations according to the invention is particularly strong at certain concentration ratios. However, the weight ratio of active compound in the active compound may vary within a relatively wide range. In general, from 0.01 to 1,000 parts by weight, preferably from 0.02 to 500 parts by weight and particularly preferably from 0.05 to 100 parts by weight of the active compound of group 2 per 1 part by weight of active compound of formula (I) are present.
[180] Of the active compounds of group 3, the following mixed components can be particularly emphasized:
[181] Methylhexyl 5-chloro-quinoxaline-8-oxy-acetate (cloquintocet-mexyl), ethyl 4,5-dihydro-5,5- (Isoxadifen-ethyl) and diethyl 1- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate 4-aza-spiro [4.5] -decane (AD-67), 1-dichloroacetyl-hexahydro-3 , 3,8-trimethylpyrrolo [1,2-a] pyrimidin-6 (2H) -one (BAS-145138), 4-dichloroacetyl- , 4-benzoyl (benzoxacor), 2,2-dichloro-N, N-di-2-propenyl-acetamide (dichloromide), 3-dichloroacetyl- 2,2-dimethyloxazolidine (furilazole, MON-13900) and 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148).
[182] Among the many known toxic emollients or antidotes capable of antagonizing the deleterious effects of herbicides on crops, the active compounds of Group 3 mentioned above do not adversely affect the herbicidal effect on weeds, It is considered surprising that the compounds of the general formula (I) combined with the active compounds of group 2 and their salts are almost completely antagonistic to the harmful effects on the crops.
[183] Surprisingly, it has further been found that 2,4-dichlorophenoxy-acetic acid (2,4-D), a herbicidally active substance, and its derivatives can act as the toxic emollients described above.
[184] Thus, certain embodiments may also optionally include one or more of the above-mentioned active compounds of Group 2, while the compounds of Formula (I) and / or its salts and, on the other hand, 2,4-D and / or Or a derivative thereof. Representative derivatives of 2,4-D are, for example, esters thereof.
[185] Surprisingly, it has also been found that (4-chloro-2-methylphenoxy) acetic acid (MCPA) and (+) - 2- It was found to work as a mitigating agent. The compounds mentioned are described in patent applications JP 63 072 605 and GB 00 820 180.
[186] The compound was synthesized from diethyl 1- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr- (Trichloromethyl) -1H-1, 2,4-dichloro-2- (4-fluorophenyl) -5- (trichloromethyl) -Triazole-3-carboxylate (pancolasol-ethyl) is described in patent applications DE-A-39 39 503, EP-A-191 736 and DE-A-35 25 205. 2,4-D is a known herbicide.
[187] Advantageous crop compatibility effects of the active formulations according to the invention are likewise particularly excellent at certain concentrations. However, the weight ratio of active compound in the active compound may vary within a relatively wide range. In general, mention may be made of (c) above, which improves crop compatibility of 0.001 to 1,000 parts by weight, preferably 0.01 to 100 parts by weight and particularly preferably 0.1 to 10 parts by weight per 1 part by weight of the active compound of formula (I) (Antidote / toxic emollient). ≪ / RTI >
[188] According to the present invention, whole plants and parts of plants can be treated. Here, a plant means any plant and plant populations, such as wild or unwanted wild plants or crops (including ungulates). Crops can be obtained by conventional breeding and optimization methods, including plant cultivars and transgenic plants, which can be protected or can not be protected by plant breeding assurances, by biotechnological and recombinant methods, or by combining these methods It can be a plant. A part of a plant means all the ground and underground parts and organs of a plant such as buds, leaves, flowers and roots, for example leaves, needles, stalk, trunk, , Fruits, fruits, seeds, roots, tubers and rootstocks may be mentioned. Some of the plants also include nutritive and reproductive material, such as seedlings, tubers, rootstocks, cuttings and seeds.
[189] The treatment of plants and parts of plants with active compounds according to the invention can be carried out directly or by conventional treatment methods, for example by immersion, spraying, evaporation, spraying, spraying or application, By acting as a mono- or multi-layer coating on its surroundings, environment or storage space.
[190] Among plants obtained by biotechnology and recombinant methods, or a combination of these two methods, plants with resistance to so-called ALS, 4-HPPD, EPSP and / or PPO inhibitors are highlighted, for example Acuron plants.
[191] Active formulations according to the invention can be used, for example, in the following plants:
[192] Dicotyledonous weeds in the genus :
[193] Abu epothilone (Abutilon), probably Lantus (Amaranthus), Ambrosia (Ambrosia), Arnaud is (Anoda), Ante Miss (Anthemis), sick ness (Aphanes), art Reflex (Atriplex), belriseu (Bellis), a non-dense (Bidens ), capsule La (Capsella), carboxylic Douce (Carduus), cassia (Cassia), center urea (Centaurea), Ke-established rhodium (Chenopodium), unsealing syum (Cirsium), convolution bulruseu (Convolvulus), Datura (Datura), death modium (Desmodium), the Mex (Emex), Erie during drought (Erysimum), yuporeubiah (Euphorbia), Gale option system (Galeopsis), ground Soga (Galinsoga), gallium (Galium), Hibiscus (Hibiscus), Ipomoea , Kochia , Lamium , Lepidium , Lindernia , Matricaria , Mentha , Mercurialis , Mullugo , Myosotis , Papaver , Pharbitis , Plantago , Polygonum, (Polygonum), Make FORT Tula car (Portulaca), La nunkul Ruth (Ranunculus), Rafa Augustine (Raphanus), roripa (Rorippa), as Tala (Rotala), Lou Mex (Rumex), buy Solar (Salsola), Sene ( Senecio), access Vania (Sesbania), let (Sida), Sina-piece (Sinapis), Solar num (Solanum), hand kusu (Sonchus), Spanish no nuclease (Sphenoclea), Stella Liao (Stellaria), fall sakum (Taraxacum) , Tralee RY (Thlaspi), Tripoli Stadium (Trifolium), Ur Utica (Urtica), Veronica (Veronica), viola (viola), greater santyum (Xanthium).
[194] Dainted crops of the following species :
[195] Arachis (Arachis), beta (Beta), Brassica (Brassica), Cucumis (Cucumis), Cuckoo Le Vita (Cucurbita), Tooth (Helianthus) do not patronize, Dow Syracuse (Daucus), Glee Cinemax (Glycine), Notice europium (Gossypium), Ipoh Moe Oh (Ipomoea), Rock Dukas (Lactuca), rinum (Linum), Rico Percy cone (Lycopersicon), Nico tiahna (Nicotiana), Pace come loose (Phaseolus), pisum (Pisum), Solar num Solanum , Vicia .
[196] Weeping weeds in the following species :
[197] Oh, way to the rope's (Aegilops), Agrobacterium Piron (Agropyron), Agrobacterium seutiseu (Agrostis), Alor page kuruseu (Alopecurus), ahpera (Apera), ABE or (Avena), beuraki Aria (Brachiaria), bro Moose (Bromus) Sen Cruz (Cenchrus), nose Melina (Commelina), Sino money (Cynodon), between Peru's (Cyperus), daktil lock'll help (Dactyloctenium), D. other Ria (Digitaria), Echinacea-no claws ah (Echinochloa), Eleanor Eleocharis , Eleusine , Eragrostis , Eriochloa , Festuca , Pimbristylis , Heteranthera , Imperata , Imperata , Ischaemum , Leptochloa , Lolium , Monochoria , Panicum , Paspalum , Phalaris , Flemish, Phleum , Poa , Rottboellia , Sagittaria , S cirpus , Setaria , Sorghum .
[198] Cotton crops in the following :
[199] Allium (Allium), Ananas (Ananas), aspartate Goose (Asparagus), ABE or (Avena), Johor deum (Hordeum), duck party (Oryza), Trapani Qom (Panicum), Saccharomyces Room (Saccharum), three-Calais ( Secale), sorbitol gum (Sorghum), Tea tree Calais (Triticale), the tree tikum (Triticum), ZE (Zea).
[200] However, the use of active formulations according to the present invention is not limited to the above, and extends to other plants in the same manner.
[201] The active compounds used according to the invention can be used in conventional cultivation methods (preferably at regularly spaced crops) in cultivated crops (e.g. vines, fruits, citrus fruits) and in industrial areas and railroads, And can be used as a minimum cultivation method. They are also suitable as a desiccant (for example as a stem remover from potato) or as a leaf agent (for example from cotton). They are also suitable for use on non-cultivated ground. Other applications are the trestle, forests, pastures and ornamental products.
[202] The active formulations can be in the form of solutions, emulsions, wettable powders, suspensions, powders, powders, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compounds, It can be converted into a conventional preparation.
[203] These preparations are prepared in a known manner, for example by mixing the active compounds with extenders, i. E. Liquid solvents and / or solid carriers, optionally using surfactants, i.e. emulsifiers and / or dispersants and / or foam formers.
[204] When water is used as the extender, for example, an organic solvent can also be used as a co-solvent. The liquid solvents include aromatic compounds such as xylene, toluene or alkylnaphthalene, chlorinated aromatic and chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, cyclohexane or paraffins such as mineral oil fractions, mineral oils and vegetable oils, Alcohols such as aliphatic hydrocarbons, butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl formamide and dimethyl sulfoxide, as well as water Suitable.
[205] Suitable solid carriers are, for example, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silicas, alumina and silicates to be. Suitable solid carriers for granules are, for example, granulated and classified natural rocks such as calcite, marble, pumice, hemastone and dolomite, and synthetic granules of inorganic and organic powders, and organics such as sawdust, coconut shells, cornstalks and tobacco stalks. It is a granule of matter. Suitable emulsifiers and / or foam formers include, for example, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers such as alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl Sulfonate or protein hydrolyzate. Suitable dispersants are, for example, lignin sulfite waste and methylcellulose.
[206] Adhesives such as natural and synthetic polymers in the form of powders, granules or latex, such as carboxymethylcellulose, gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids such as cephalin and lecithin, and synthetic phosphatides, . Other additives can be unique to mineral oil and plants.
[207] Coloring agents such as inorganic pigments such as iron oxide, titanium oxide and prussian blue and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes and salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc Micronutrients may also be used.
[208] The preparations generally contain from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight, of the active compound.
[209] The active formulations according to the invention are generally applied in the form of a ready mix. However, the active compounds contained in the active formulations may also be applied in the form of individual preparations, i.e. tank mixes, which are mixed at the time of use.
[210] The novel active formulations may be used as a mixture with known herbicides on their own or in the form of their formulations, and ready to mix or tank mixes are possible. Mixtures with other known active compounds such as fungicides, insecticides, acaricides, nematicides, algicides, growth materials, plant nutrients and soil conditioners are also possible. Mineral oil or vegetable oil (for example the commercial product "Rako Binol") or an ammonium salt, for example ammonium sulfate or ammonium thiosulfate, as a further additive in the preparation, for particular application purposes, May also be advantageous.
[211] The novel active formulations can be used as such, in the form of their formulations or in their use forms, for example ready-to-use solutions, suspensions, emulsions, powders, pastes and granules, which can be prepared by further diluting these formulations. They are used in a conventional manner, for example by pouring, spraying, atomizing, dispersing or broadcasting.
[212] The active compound according to the present invention can be applied both before and after the emergence of the plant, that is, both before and after germination. They may also be incorporated into the soil before sowing.
[213] The superior herbicidal action of the novel active formulations according to the invention is evidenced by the following examples. While individual active compounds are weak in terms of herbicidal action, all of the formulations exhibit very good activity, merely aggregating action on weeds.
[214] The synergistic effect of herbicides is always present when the herbicidal action of the active compound overcomes the action of the active compound applied individually.
[215] The expected activity for the given two herbicide combinations can be calculated as follows (see COLBY, S.R., "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, pages 20-22, 1967):
[216] E = X + Y - (X 占 Y / 100)
[217] In this formula,
[218] X is the damage rate (%) when the herbicide A (the active compound of formula (I)) is applied at an application rate of p kg /
[219] Y is the damage rate (%) when applying the herbicide B (active compound of formula (II)) at the application rate of q kg /
[220] E is the expected rate of damage if the herbicides A and B are applied at application rates of p and q kg /..
[221] If the actual damage rate exceeds the calculated value, the combination has the effect of being superadditive, i.e. there is a synergistic effect.
[222] The theoretical predictive activity for a given herbicidal combination can likewise be confirmed by the above mentioned references.
[223] Use Example :
[224] Example A
[225] Pre-germination test
[226] Solvent: 2 to 3 parts by weight of acetone or N, N-dimethylformamide
[227] Emulsifier: alkylaryl polyglycol ether 1 part by weight
[228] One part by weight of the active compound is mixed with the above-mentioned amount of the solvent, the emulsifier is added in the amount mentioned above, and the concentrate is diluted with water to the desired concentration to prepare a suitable preparation of the active compound. The formulated product was dissolved in water and diluted with water to the desired concentration.
[229] Solutions of other mixed ingredients (active compound or toxic emollient) were similarly prepared. Thereafter, a solution of the various mixed ingredients separately prepared was blended and, if necessary, additional substances (formulation auxiliaries, additives, etc.) were added, and water was optionally added to dilute to the desired degree.
[230] The seeds of the test plants were inoculated into the soil. After 24 hours, the active compound preparation in the soil was sprayed in each case so that a certain amount of the desired active compound was applied per unit area. The concentration of active compound in the spray liquor was chosen so that in each case a certain amount of the desired active compound was applied in 500 l of water per hectare. The container containing the test plants was placed in a greenhouse with temperature and lighting adjusted until evaluation.
[231] Three weeks later, the degree of damage to the plant was recorded as percent damage compared to untreated controls.
[232] The numbers indicate:
[233] 0% = no effect / no damage (same as non-treated control)
[234] 100% = Complete control
[235] In this test, for example, the compound (I-3) and the compound 4-dichloroacetyl-1-oxa-4-aza-spiro [4.5] -decane (AD- The combination of lomethyl-thiazole-5-carboxylate (flurasol) showed much better compatibility with, for example, corn-like crops than with compound (I-3) alone (see Table A1).
[236] Table A1 : Pre-germination test in corn
[237]
[238] All strains were treated with 0.1% Renex-36 in spray solution.
[239] Further, in the above test, the compound (I-6) and the compound diethyl 1- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (Mefenpyr-diethyl) showed much better compatibility with crops such as barley and wheat than with compound (I-6) alone (see Table A2).
[240] Table A2 : Tests after germination in barley mill
[241]
[242] All strains were treated with 0.1% Renex-36 in spray solution.
[243] In this test, the compound (I-6) and the compound 1-methylhexyl 5-chloro-quinoxaline-8-oxy-acetate (cloquintocet-mexyl) and ethyl 1- (2,4-dichlorophenyl) (I-6) than in the case of compound (I-6) alone, even in the case of crops such as barley and wheat And exhibited excellent compatibility (see Table A3).
[244] Table A3 : Post-germination tests in barley and wheat
[245]
[246] All strains were treated with 0.1% Renex-36 in spray solution.
[247] Also, in the above test, the combination of the compound (I-6) and the compound 2,2-dichloro-N, N-di-2-propenyl-acetamide (dichloromide) For example, crops such as barley and wheat (see Table A4).
[248] Table A4 : Tests after germination in barley and wheat
[249]
[250] All strains were treated with 0.1% Renex-36 in spray solution.
[251] In addition, in the above test, the combination of the compound (I-6) and the compound 4,6-dichloro-2-phenyl-pyrimidine (pancylorum) is more effective than the compound (1-6) alone, And showed much better compatibility with the crops (see Table A5).
[252] Table A5 : Post-germination tests in barley and wheat
[253]
[254] All strains were treated with 0.1% Renex-36 in spray solution.
[255] Further, in this test, the combination of the compound (I-6) and the compound 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4- benzoxazole (berdoxacor) ) Than in the case of single crops (see Table A6).
[256] Table A6 : Tests after germination in barley and wheat
[257]
[258] All strains were treated with 0.1% Renex-36 in spray solution.
[259] Also in this test, the combination of compound (I-3) with compound 2,4-D and glyphosate-isopropylammonium showed significant synergistic activity (see Table A7).
[260] Table A7 : Post-germination test (Values in parentheses are values calculated according to Colby formula)
[261]
[262] Table A7 - Continued
[263]
[264] Also in this test, the combination of compound (I-3) and the compound sulfenotrone showed significant synergistic activity (see Table A8).
[265] Table A8 : Post-Germination Test (Values in parentheses are values calculated according to Colby formula)
[266]
[267] Also in this test, the combination of compound (I-3) and compound imazamox exhibited significant synergistic activity (see Table A9).
[268] Table A9 : Post-Germination Tests (Values in parentheses are values calculated according to Colby formula)
[269]
[270] Also in this test, the combination of compound (I-3) and the compound acetochlor exhibited significant synergistic activity (see Table A10).
[271] Table A10 : Pre-germination test (Values in parentheses are values calculated according to Colby formula)
[272]
[273] Also in this test, the combination of compound (I-3) and the compound metholachlor showed a considerable synergistic activity (see Table A11).
[274] Table A11 : Pre-germination test (Values in parentheses are values calculated according to Colby formula)
[275]
[276] In addition, in this test, the combination of compound I-3 and compound isoxaflutole exhibited significant synergistic activity (see Table A12).
[277] Table A12 : Pre-germination test (values in parentheses are values calculated according to Colby formula)
[278]
[279] Also in this test, the combination of compound (I-3) and compound flupenase exhibited significant synergistic activity (see Table A13).
[280] Table A13 : Pre-germination test (values in parentheses are values calculated according to Colby formula)
[281]
[282] Also in this test, the combination of the compound (I-3) and the compound methotrexine showed significant synergistic activity (see Table A14).
[283] Table A14 : Pre-germination test (Values in parentheses are values calculated according to Colby formula)
[284]
[285] Also in this test, the combination of the compound (I-3) and the compound amikavazone showed a considerable synergistic activity (see Table A15).
[286] Table A15 : Pre-germination test (Values in parentheses are values calculated according to Colby formula)
[287]
[288] Also in this test, the combination of compound (I-3) and the compound sulcotrione showed significant synergistic activity (see Table A16).
[289] Table A16 : Pre-germination test (Values in parentheses are values calculated according to Colby formula)
[290]
[291] Also in this test, the combination of compound (I-3) with the compound flupenase and amikarbazone exhibited significant synergistic activity (see Table A17).
[292] Table A17 : Pre-germination test (Values in parentheses are values calculated according to Colby formula)
[293]
[294] Also in this test, the combination of compound (I-3) with the compound flupenase and methotrexine showed significant synergistic activity (see Table A18).
[295] Table A18 : Pre-germination test (values in parentheses are values calculated according to Colby formula)
[296]
[297] Table A18 - Continued
[298]
[299] Also in this test, the combination of compound (I-3) with the compound flupenase and amicabazone exhibited significant synergistic activity (see Table A19).
[300] Table A19 : Pre-germination test (Values in parentheses are values calculated according to Colby formula)
[301]
[302] Also in this test, the combination of compound (I-3) and the compound acetochlor exhibited significant synergistic activity (see Table A20).
[303] Table A20 : Pre-germination test (values in parentheses are values calculated according to Colby formula)
[304]
[305] Also in this test, the combination of compound (I-3) and the compound flupenase exhibited significant synergistic activity (see Table A21).
[306] Table A21 : Pre-germination test (Values in parentheses are values calculated according to Colby formula)
[307]
[308] Also in this test, the combination of compound (I-3) and the compound amikavazone exhibited significant synergistic activity (see Table A22).
[309] Table A22 : Pre-germination test (Values in parentheses are values calculated according to Colby formula)
[310]
[311] Also in this test, the combination of compound (I-3) with the compound flupenase and methotrexine showed significant synergistic activity (see Table A23).
[312] Table A23 : Pre-germination test (Values in parentheses are values calculated according to Colby formula)
[313]
[314] Table A23 - Continued
[315]
[316] Also in this test, the combination of compound (I-3) with the compound trifluralin exhibited significant synergistic activity (see Table A24).
[317] Table A24 : Pre-germination test (values in parentheses are values calculated according to Colby formula)
[318]
[319] Also in this test, the combination of compound (I-3) and the compound atrazine showed significant synergistic activity (see Table A25).
[320] Table A25 : Pre-germination test (Values in parentheses are values calculated according to Colby formula)
[321]
[322] Also in this test, the combination of compound (I-3) and the compound coixturtol and methotrexine showed significant synergistic activity (see Table A26).
[323] Table A26 : Pre-germination test (Values in parentheses are values calculated according to Colby formula)
[324]
[325] Table A26 - Continued
[326]
[327] Also in this test, the combination of compound (I-3) with the compound polamsulfuron exhibited significant synergistic activity (see Table A27).
[328] Table A27 : Pre-germination test (values in parentheses are values calculated according to Colby formula)
[329]
[330] In this test it is also possible to demonstrate that certain compounds of group 3 can antagonize the damaging effects of the active compounds of formula (I) on crops (see Tables A28-A32).
[331] Table A28 : Pre-germination test in corn
[332]
[333] Table A29 : Pre-germination test in corn
[334]
[335] Table A30 : Pre-germination test in corn
[336]
[337] Table A31 : Pre-germination test in corn
[338]
[339] Table A32 : Pre-germination test in corn
[340]

权利要求:
Claims (12)
[1" claim-type="Currently amended] (a) at least one N-aryl-uracil of the general formula (I) (" active compound of group 1 &
(b) 2-Chloro-N- (ethoxymethyl) -N- (2-ethyl-6-methyl-phenyl) -acetamide (acetochlorine) Phenoxy) -2-nitro-benzoic acid sodium salt (acifluorfen-sodium), 2-chloro-6-nitro- ) -N- (2,6-diethyl-phenyl) -acetamide (allachlor), N-ethyl-N'-i-propyl-6-methylthio-1,3,5-triazine- - diamine (ametryne), 4-amino-N- (1,1-dimethyl-ethyl) -4,5-dihydro- 4-triazole-1-carboxamide (Amicabazone), N- (4,6-dimethoxy-pyrimidin- ) - urea (amidosulfuron), 1H-1,2,4-triazole-3-amine (amitrol), 6-chloro- Azine (atrazine), 2- [2,4-dichloro-5- (2-propynyloxy) -phenyl] -5,6,7,8-tetrahydro-1,2,4- triazolo- [ 3, a] -pyridin-3 (2H) -one ( Methyl-4- (2-methyl-2H-tetrazol-5-yl) -lH-quinazolin- Benzyl-2- (4-fluoro-3-trifluoromethyl-phenoxy) -butanamide (beflubutamide), 4- N-butyl-N-ethyl-2,6-dinitro-4-trifluoromethyl-benzenamine (benz flouraline), Methyl-2- [2- [4- (2-methoxycarbonylphenylmethylsulfonyl) -urea (benzenesulfonyl) Methyl-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinyl) phenoxy] methyl] -5-ethyl-phenoxy- Yl) -4-phenylthio-bicyclo- [3.2.1] -oct-3-en-2-one (benzoficyclone), 3- (2-chloro-4-methylsulfonyl- Benzyl-N- (3,4-dichloro-phenyl) -DL-alaninate (benzoylprop-ethyl), 3-i-propyl-1H-2,1,3-benzothiadiazole -4 (3H) -one (benzazone), methyl 5- (2,4-dichloro-phenoxy) -2-nitro- benzoate (bifenox), 2,6- (LH, 3H) - benzoic acid sodium salt (bispyryl-sodium), 5-bromo-6-methyl-3- (2-bromo-3,3-dimethyl-N- (1 -methyl-1-phenyl- ethyl) -butanamide (bromobutide), O- 4-hydroxy-benzonitrile (bromocinnamyl), N- (4-hydroxy-benzoyl) (2-propenyloxy)] - (2-fluoro-phenyl) -acetamide Ethyl 2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-l (2H) -pyrimidinyl) -benzoate (butapenacyl- Allyl), 2- (1-ethoximino-propyl) -3-hydroxy-5- [2,4,6-trimethyl- -On (Butyloxydim), S-ethylbis- (2-methyl-propyl) -thiocarbamate (butylate), N, 2-propenyl) -oxy-imino] -propyl] -3- (3-chloro-2- 2-cyclohexen-1-one (carboxydim, teflaloxydim), 2- (4-chloro-2-fluoro- - (2-chloro-2-ethoxycarbonyl-ethyl) -phenyl) -4-difluoromethyl-5-methyl- Benzene (chloromethoxyphene), 3-amino-2,5-dichloro-benzoic acid (chloromethoxyphene), 3-amino- (Chloromethyl-ethyl), (4-chloro-6-methoxy-pyrimidin-2-yl) Methoxy-6-methyl-1,3,5-triazine-2- (4-nitro-phenoxy) Yl) -N ' - (2-chloro-phenylsulphonyl) Chloro-3- [2-chloro-4-methyl-phenyl) -N, N-dimethyl-urea (chlorotoluron) Yl) -phenyl] -2-propanoate (cinidon-ethyl), < RTI ID = 0.0 & - (2-methoxy-ethoxy) -phenylsulfonyl) -urea (cynosulfuron < ), 2- [1- [2- (4-chloro-phenoxy) -propoxyamino] butyl] -5- (tetrahydro-2H-thiopyran-3- yl) -1,3-cyclohexanedione (E) - (+) - 2- [1 - [[(3-chloro-2-propenyl) -oxy] -imidopropyl] -3- hydroxy- (4-chloro-3-fluoro-pyridin-2-yl-oxy) -phenoxy] -propyl} Chloro-2 - [(5-ethoxy-7-fluoro [1,2, 3- dihydro- 4] triazolo [1,5-c] pyrimidin-2-yl-sulfonyl) - Amino] -benzoate (chloranesulam-methyl), 2-chloro-4-ethylamino-6- (1-cyano- (2-cyclopropylcarbonyl-phenylsulfonyl) -urea (cyclosulfamuron), 2- (1-ethoximino Butyl) -3-hydroxy-5- (tetrahydro-2H-thiopyran-3-yl) -2-cyclohexen- 2-fluoro-phenoxy) -phenoxy] -propanoate (cyhalofop-butyl), 2,4-dichloro-phenoxyacetic acid (2,4- Dichloro-2-methoxy-benzoic acid (dicamba), (R) -2- (2,4-dichloro-phenoxy) propanoic acid (dichlorprop- Dichloro-phenoxy) -phenoxy] -propanoate (diclofop-methyl), N- (2,6-dichloro-phenyl) -5-ethoxy- 4] -triazolo- [1,5-c] -pyrimidine-2-sulfonamide (diclosylam), 1,2-dimethyl-3,5-diphenyl-1H-pyrazolium methyl 2 (2-trifluoromethyl-phenoxy) -pyridine-3-carboxamide (difluorenecane), 2 (Diphenylphosphon), S- (1-methyl-1-phenyl-ethyl) -pyridine- (2-methoxy-ethyl) -acetamide (prepared from 2-chloro-N- (2,6-dimethyl- Dimerchlor), (S-) 2-chloro-N- (2,4-dimethyl-3-thienyl) -N- (2-methoxy- Methyl-ethyl) -6- (1-methyl-2- (3,5-dimethyl-phenoxy) -ethylamino) -1, N3, diethyl-2,4-dinitro-6-trifluoromethyl-1,3-diamino-benzene (dinitramine), 6,7 -Dihydro-dipyrido [1,2-a: 2 ', 1'-c] pyrazine di (dicouat), S, S-dimethyl 2-difluoromethyl- Fluorome (Pyridin-3,5-dicarbothioate (dithiopyr), N '- (3,4-dichloro- phenyl) -N, N-dimethyl- (Phenylmethyl) -2-ethyl-1H-indene-1,3 (2H) -dione (Ephroptan), S-ethyldipropylthiocarbamate (EPTC) Ethyl-N- (2-methyl-2-propenyl) -2,6-dinitro-4- (S) -2-chloro-5- (2-chloro-4-trifluoromethyl-phenoxy) -pyridine ) - benzoate (ethoxyphene), N- (4,6-dimethoxy-pyrimidin-2-yl) -N ' (P) -ethyl), 4- (2-chloro-benzooxazol-2-yl-oxy) -phenoxy] - phenyl) -N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide (pentrazamid), isopropyl (3-chloro-4-fluoro-phenyl) -DL-alaninate (flampprop-isopropyl), isopropyl N-benzoyl-N- Phenyl) -L-alaninate (flampprop-isopropyl-L), methyl N-benzoyl-N- (3-chloro-4-fluoro-phenoxy) -Methyl), N- (2,6-difluoro-phenyl) -8-fluoro-5-methoxy- [1,2,4] -triazolo- [ 2-sulfonamide (flasilam), butyl (R) -2- [4- (5-trifluoromethyl-pyridin-2-yl- oxy) -phenoxy] -propanoate (fluazifop, Methyl-5-trifluoromethyl-lH-pyrazol-3-yl) -2-chloro-4-fluoro-benzoate (Fluazolate), 4,5-dihydro-3-methoxy-4-methyl-5-oxo- N - [(2-trifluoromethoxy- phenyl) -sulfonyl] (4-triazole-1-carboxamide sodium salt (flucarbazone-sodium), N- (4-fluoro- phenyl) (2,2-difluoro-phenyl) -5-methyl-1,2, < / RTI > (2-chloro-4-fluoro-5- (1, 3, 4, 5, 6, 7) -triazolo [1,5-a] -pyrimidine- -Hexahydro-1,3-dioxo-2H-isoindol-2-yl) -phenoxy] -acetate (fumiclolactopentyl), 2- [7-fluoro-3,4- 4- (2-propynyl) -2H-1,4-benzoxazin-6-yl] -4,5,6,7-tetrahydro-1H-isoindole- Methyl-2-propynyl) -oxy] -phenyl] -4,5,6,7-tetrahydro-1H-iso Indole-1,3 (2H) -dione (flumiprofen), 3-chloro-4-chloromethyl-1- (3-trifluoromethyl- phenyl) -2- pyrrolidone (fluorochloridone) (Fluoroglycophene-ethyl), 1- (4-chloro-3- (2 (trifluoromethyl) , 2,3,3,3-pentafluoro- 5-phenyl-1H-1,2,4-triazole-3-carboxamide (fluoxam), 1-isopropyl-2-chloro-5- (3,6-dihydro (2H) -pyrimidyl) -benzoate (fluproprosyl), N- (4,6-dimethoxy-pyrimidin-2 -Urea sodium salt (flupyrsulfuron-methyl-sodium), 9-hydroxy- (3-methoxycarbonyl-6-trifluoromethyl-pyridin- (2-butoxy-1-methyl-pyridin-4-yl) -9H-fluorene-9-carboxylic acid (fluoranol) (3-trifluoromethyl-phenyl) -3 (2H) -quinolinone was obtained in the same manner as in Example 1, 3-oxo-lH, 3H- [l, 3,4] -thiadiazolo- [3,2-d] pyrimidin- 4-a] -pyridazin-1-ylidene) -amino) -phenyl] -thio-acetate (fluthiasset- 2-chloro-4-trifluoromethyl-phenoxy) -N-methylsulfonyl-2-nitro-benzamide (pomesafen), 2 - [[[[(4,6-dimethoxy- (2-amino-4- (hydroxymethylphosphinyl) carbonyl] -amino} -sulfonyl] -4-formylamino-N, N-dimethyl- (R) -2- [4- (3-tert-butoxycarbonyl) amino] propionic acid, (Methyl ester, 2-ethoxy-ethyl ester, butyl ester) (Haloxyfop, -methyl, -P-t-butyldimethylsilyloxy) -phenoxy] (1H, 3H) -dione (hexaquinone), methyl 3-cyclohexyl-6-dimethylamino-1-methyl-1,3,5-triazine- Methyl-benzoate (imazametabenz-methyl), 2- (4,5-dihydro-4-methyl-4-isopropyl- (4,5-dihydro-4-methyl-4- Methyl-pyridine-3-carboxylic acid (imazametaphyr), 2- (4,5-dihydro-4-methyl-4-iso Imidazol-2-yl) -5-methoxymethyl-pyridine-3-carboxylic acid (imazamox), 2- (4,5-dihydro- (4,5-dihydro-4-methyl-4-i-isopropyl-5-oxo-propyl) Yl) -N ' - (2- (2, < / RTI > 2-dimethoxy- (Imazosulfuron), N- (4-methoxy-6-methyl-1,3,5-triazine-pyrimidin- 2-yl) -N '- (5-iodo-2-methoxycarbonyl-phenylsulfonyl) -urea sodium salt (iodosulfuron- methyl- sodium), 4-hydroxy- N-dimethyl-N '- (4-isopropyl-phenyl) -urea (isoproterone), N- (3- ) -Isoxazol-5-yl) - (Isoxanthol), (4-chloro-2-methylsulfonyl-phenyl) - (5-cyclopropyl-isoxazol- (Isoxaflutole), 2- [2- [4 - [(2-methylsulfonyl-4- trifluoromethyl- (2-ethoxy-1-methyl-2-oxo < / RTI > (3-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoate (lactophene) (MCPA), 2- (4-chloro-2-methyl-phenoxy) -propionic acid (methoprotein) (2-benzothiazolyloxy) -N-methyl-N-phenyl-acetamide (mepenacet), methyl 2 - [[[[(4,6- dimethoxy-2-pyrimidinyl) amino ] Carbonyl] amino] sulfonyl] -4 - [[(methylsulfonyl) amino] methyl] -benzoate (methosulfuron) Amino-3-methyl-6-phenyl-l, 2,4-triazine-5 (4H) -one (Methaimuron), N ' - (4-methoxyphenyl) -N- (lH-pyrazol- (3,4-dihydro-2-methoxy-2,4,4-trimethyl-2H- 1 -benzopyran-7-yl-oxy) -phenyl) -N-methoxy-N-methyl- (S) -2-chloro-N- (2-ethyl-6-methyl-pyrimidin- (2-methoxy-1-methyl-ethyl) -acetamide (metolachlor, S-metolachlor), N- (2,6- (3-chloro-4-methoxy-phenyl) - < / RTI > N-dimethyl-urea (methoxydone), 4-amino-6-t-butyl-3-methylthio-1,2,4-triazine-5 (4H) (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '-( 2-methoxycarbonyl- (2-naphthyloxy) -N-phenyl-propanamide (methanesulfuron-methyl), S-ethyl-hexahydro-1H-azepine- (Neproanilide), N- (4,6-dimethoxy-pyrimidin-2-yl) -N- (3-dimethylcarbamoyl-pyridin-2-yl-sulfonyl) -urea (nicosulfuron), 4-chloro-5-methylamino- 3 (2H) -pyridazinone (Norflurazone), S- (2-chloro-benzyl) -N, N-diethyl- (2,4-dichloro-5- (2-propynyloxy) -phenyl] -5- (t-butyl) -1,3,4-oxadiazole- 2- (3H) -one (oxadialgyl), 3- [2,4-dichloro-5- (1-methyl-ethoxy) -phenyl] Oxadiazol-2 (3H) -one (oxadiazon), N- (4,6-dimethyl-pyrimidin- Phenylsulfonyl) -urea (< / RTI > Methyl-5-phenyl-4H-1, 3-oxazin-4-yl) 4-nitro-phenoxy) -4-trifluoromethylbenzene (oxyfluorfen), 1,1'-dimethyl-4 , 4'-bipyridinium (paracouat), 1-amino-N- (1-ethyl-propyl) -3,4-dimethyl-2,6-dinitro- (4-amino-3,5,6-trichloro-pyridine-2-carboxylic acid Pyridine-2-carboxamide (picolinafen), 2-chloro-N- (2, 3-difluoro- (2-propoxy-ethyl) -acetamide (pretilachlor), N- (4,6-bisdifluoromethoxy-pyrimidin- Chloro-4-fluoro-5 - [(6S, 7aR) -6- (2-methoxycarbonyl-phenylsulfonyl) -urea Fluorotetrahydro-1,3-di (2-chloro-N-isopropyl-N-phenyl-acetic acid) (Propyl), (R) - [2 - [[(1-methylethylidene) amino] -oxy] -ethyl 2-chloro-N- (2-ethyl-6-methyl-phenyl) -pyridin- Methyl-ethoxy) -acetamide (propyl chloride), methyl 2 - [[[(4,5-dihydro-4-methyl- -1H-1,2,4-triazol-1-yl] -carbonyl] -amino] -sulfonyl] -benzoate sodium salt (propoxycarbazone- sodium), S- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2- (3,3,3- (4-chloro-5-difluoromethoxy-l-methyl-lH-pyrazol-3- Yl) -4- Pyrazolo [1,5-a] pyridin-2-yl) - (4-chloro-pyridin- 4-carbonitrile (pyrazolidyl), 4- (2,4-dichloro-benzoyl) -1,3-dimethyl-5- (Pyrazolate), 4- (2,4-dichloro-benzoyl) -1,3-dimethyl-5- (phenylcarbonylmethoxy) , N - (4-ethoxycarbonyl-1-methyl-pyrazol-5-yl-sulfonyl) -urea (pyrazosulfuron (Ethyl), O- [2,6-bis- (4,6-dimethoxy-pyrimidin-2-yl-oxy) -benzoyl] diphenylmethanone- oxime Phenyl-pyridazinol (pyridapol), O- (6-chloro-3-phenyl-pyridazin-4-yl) S-octylthiocarbonate (pyridate) (Pyrihydol), 7 - [(4,6-dimethoxy-2-pyrimidinyl) -thio] -3-methyl-1 (3H) -isobenzofuranone , Methyl 2- (4,6-dimethoxy-pyrimidin-2-yl-oxy) -benzoate (pyriminobak-methyl), 2-chloro-6- (4,6-dimethoxy-pyrimidin- -Quinoline-8-carboxylic acid (quinomelac), 3-methyl-quinoline-8-carboxylic acid (quinclorac) (Ethyl ester, tetrahydro-2-furanyl-methyl ester) (quizalofopro, -ethyl, -P -Ethyl, -P-terfuryl), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (3-ethylsulfonyl-pyridin- (2-ethylthiopropyl) -3-hydroxy-2-cyclohexen-1-one (cetoxydim), 6-chloro- (2-chloro-4-methylsulfonyl-benzoyl) -cyclohexane-1,3-dione (sulcotrione), 4-bis- 2- (2,4-Dichloro-5-methylsulfonylamino-phenyl) -4-difluoromethyl-5-methyl- Amino] carbonyl] amino] sulphonamide (hereinafter referred to as " methyl 2 - [[[[ (4-trifluoromethyl-phenyl) -benzoate (sulfomethuron-methyl), N-phosphonomethyl-glycine-trimethylsulfonium (sulfosate) (2-ethylsulfonyl) -imidazo [1,2-a] pyridine-3-sulfonamide (sulfosulfuron), 6-chloro-4-ethylamino- -Triazine (terbutaline), 2-t-butylamino-4-ethylamino-6-methylthio-1,3,5-triazine (terbutaline) (4-methoxy-2-thienyl-methyl) -acetamide (decyl chloride), methyl 2-difluoromethyl-5- 6-dimethyl-3H-pyrazole-3-carboxylate (thiazopyr), 6- (6,7-dihydro- Pyrrolo [2,1-c] -1,2,4-thiadiazol-3-ylideneamino) -7-fluoro-4- (2- Ben photo 3 ( 4H) -one (thiadiazine), N- (4-methoxy-6-methyl-1,3,5-triazin- 3-hydroxy-5- (2,4,6-trimethyl-phenyl) -2-cyclohexene- (2,3-trichloro-2-propenyl) diisopropylcarbamothioate (triallyl), N- (4-methoxy- -Methyl-1,3,5-triazin-2-yl) -N '- [2- (2-chloro-ethoxy) -phenylsulfonyl] -urea (triasulfuron) (3-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '-( 2- methoxycarbonyl- phenylsulfonyl) (3,5,6-trichloro) -pyridin-2-yl-oxy-acetic acid (trichloropyr) Carbonyl] -3- (2,2,2-trifluoro-ethoxy) - < / RTI > 2-pyridine sulfonamide sodium salt (triplocomponent), 1-amino N, N-dipropyl-4-trifluoromethyl-benzene (trifluralin), N- [4-dimethylamino-6- (2,2,2- (3-methoxy-carbonyl-phenylsulfonyl) -urea (triflusulfuron-methyl), N- (4-methoxy- (2-trifluoromethyl-phenylsulfonyl) -urea (tristosulfuron), N - [[(4 Amino] -2-pyrimidinyl) - amino] carbonyl] -3- (N-methyl-N-methylsulfonyl- 2 - [(ethylsulfonyl) amino] -5-fluoro-4-methyl-5-oxo- (3- trifluoromethyl) (&Quot; active compound of group 2 ") selected from the second group of herbicides comprising the active compound of formula
(c) Synthesis of 4-dichloroacetyl-1-oxa-4-aza-spiro [4.5] -decane (AD-67), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo [ a] -pyrimidin-6 (2H) -one (BAS-145138), 4-dichloroacetyl-3,4-dihydro- Methyl-hexyl 5-chloro-quinoxaline-8-oxy-acetate (cloquintocet-mexyl), a- (cyanomethoximino) -phenylacetonitrile (siomethynyl), 2,4- (2,4-D), 2,2-dichloro-N- (2-oxo-2- (2- propenylamino) ), N, N-di-2-propenyl-acetamide (dichloromide), N- (4-methyl- ) - urea (Dimron), 4,6-dichloro-2-phenyl-pyrimidine (pancylim), ethyl 1- (2,4- 4-triazole-3-carboxylate (pancolazol-ethyl), phenylmethyl 2-chloro-4-trifluoromethyl- 3-dioxolan-2-yl-methoxy) - alpha -trifluoro-acetophenone oxime (Fluxophenem), 3-chloro-N- (Furilazole, MON-13900), ethyl 4,5-dihydro-5,5-diphenyl-3-yne (4-chloro-2-methylphenoxy) -acetic acid (MCPA), (+) 2- (4-chloro-2-methylphenoxy) propanoic acid Dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), 2- (MG-191), 1,8-naphthalic anhydride, - (1,3-dioxolan-2-ylmethoximino) -phenylacetonitrile 2-yl-methyl) -N- (2-propenyl) -acetamide (PPG-1292), 3-dichloroacetyl -2,2,5-trimethyl-oxazolidine (R-29148), N-cyclopropyl-4 - [[(2-methoxy- (4-methoxyacetylamino) -phenyl] -sulfonyl-2-methoxy-benzamide and N - [(4-methylaminocarbonylamino) ) -Phenyl] -sulphonyl-2-methoxy-benzamide in an amount effective to improve the compatibility of the crop (an " Active Compound of Group 3 & A herbicidal composition characterized by:

In this formula,
R ¹ represents hydrogen, amino or, optionally, cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted alkyl of 1 to 5 carbon atoms,
R < ^{2 >} is optionally halogen-substituted alkyl of 1 to 5 carbon atoms,
R ³ represents hydrogen, halogen, or optionally halogen-substituted alkyl of 1 to 5 carbon atoms,
R ⁴ represents hydrogen, cyano or halogen,
R ⁵ represents cyano, thiocarbamoyl or halogen,
R ⁶ represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, hydroxyl, mercapto, amino, hydroxyamino, aminosulfonyl or halogen, or in each case not more than 6 carbon atoms, the optionally cyano-, hydroxyl -, C ₁ -C ₄ - alkoxy -, C ₁ -C ₄ - alkylcarbonylamino -, C ₁ -C ₄ - alkoxycarbonyl -, C ₂ -C ₄ - alkenyloxy (C ₁ -C ₄ -alkyl) -aminocarbonyl-, C ₂ -C ₄ -alkynyloxycarbonyl-, C ₁ -C ₄ -alkylaminocarbonyl-, di- (C ₁ -C ₄ -alkyl) -aminocarbonyl-, phenoxycarbonyl - and / or phenylaminocarbonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl or alkylamino, or having in each case not more than 6 carbon atoms in each case optionally cyano-, carboxyl-, halogen- and / or C ₁ -C ₄ - alkoxycarbonyl-substituted alkenyl, alkynyl, alkenyloxy or alkynyloxy or indicate, If those having 6 or fewer carbon atoms in the alkyl group in each case optionally halogen-or C ₁ -C ₄ - alkoxy-substituted alkylcarbonyl-amino, alkoxycarbonylamino, amino, alkylsulfonyl amino, N, N- bis - Alkylsulfonylamino or N-alkylcarbonyl-N-alkylsulfonylamino, or in each case alkyl groups having up to 6 carbon atoms and in each case by cyano or by halogen, or by C ₁ -C ₄ C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkoxycarbonyl which in each case is C ₁ -C ₄ -alkoxycarbonyl, C ₃ -C ₄ -alkenyloxycarbonyl or C ₃ -C ₄ -alkoxycarbonyl, Phenylcarbonyl-N-alkylsulfonylamino, N-pyridylcarbonyl-N-alkylsulfonylamino optionally substituted by C _1-4 -alkynyloxycarbonyl, N-furylcarbonyl-N-alkylsulfonylamino or N-thienylcarbonyl-N-alkylsulfonylamino.
[2" claim-type="Currently amended] The composition according to claim 1, wherein the active compound of Group 1
R ¹ represents hydrogen, amino or in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl or n or i-
R ² in each case optionally represents fluorine- and / or chlorine-substituted methyl, ethyl, or n or i-propyl,
R ³ represents hydrogen, fluorine, chlorine, bromine or in each case optionally fluorine- and / or chlorine-substituted methyl, ethyl or n or i-
R ⁴ represents hydrogen, cyano, fluorine, chlorine or bromine,
R ⁵ represents cyano, thiocarbamoyl, fluorine, chlorine or bromine,
R ⁶ represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, hydroxyl, mercapto, amino, hydroxyamino, aminosulfonyl, fluorine, chlorine or bromine, Is selected from the group consisting of carboxyl-, hydroxyl-, methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl N-or i-propoxycarbonyl-, allyloxycarbonyl- or propargyloxycarbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i- or s- Propylthio, n-, i- or s-butylthio, methylthio, ethylthio, n- or i-propoxy, n- or i- Methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, Amino, ethylamino, n- or i-propyl Or in each case optionally substituted by one or more substituents selected from the group consisting of cyano-, carboxyl-, fluorine-, chlorine-, bromine-, methoxycarbonyl- and / or ethoxycarbonyl Propenyloxy, butenyloxy, propynyloxy or butynyloxy, or in each case optionally fluorine- and / or chlorine-substituted -, methoxy-, ethoxy-, n- or i-propoxy-substituted acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n N- or i-propylsulfonylamino, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, N-methylsulfonylamino, N-methylsulfonylamino, N-methylsulfonylamino, N-methylsulfonylamino, N, -N-methylsulfonylamino, N-propylsulfonylamino, N-propylsulfonylamino, N-propylsulfonylamino, N-acetyl- N-methylsulfonylamino, N-methylsulfonylamino, N- (2,2-dimethylpropanoyl) -N-ethylsulfamoyl, -N-ethylsulfonylamino, N-propyl-N-ethylsulfonylamino, Nn-butyroyl- N-ethylsulfonylamino, N-ethylsulfonylamino, N-butyroyl-N-ethylsulfonylamino, Ns-butyroyl- Optionally in the form of cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t- butyl-, trifluoromethyl-, Methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted N-phenylcarbonyl -N-methylsulfonylamino, N-phenylcarbonyl-N-ethylsulfonylamino, N-thienylcarbonyl-N-methylsulfonylamino or N-thienylcarbonyl- A herbicidal composition characterized by containing a compound of formula (I).
[3" claim-type="Currently amended] The composition according to claim 1, wherein the active compound of Group 1
R ¹ represents hydrogen, amino, methyl or ethyl,
R < ^{2 >} represents in each case fluorine- and / or chlorine-substituted methyl or ethyl,
R ³ represents hydrogen, fluorine, chlorine, bromine or in each case optionally fluorine- and / or chlorine-substituted methyl or ethyl,
R ⁴ represents hydrogen, fluorine or chlorine,
R ⁵ represents cyano, thiocarbamoyl, chlorine or bromine,
R ⁶ represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, hydroxyl, mercapto, amino, hydroxyamino, aminosulfonyl, fluorine, chlorine or bromine, Is preferably selected from the group consisting of carboxyl-, hydroxyl-, methoxy-, ethoxy-, acetyl-, propionyl-, methoxycarbonyl- and / or ethoxycarbonyl-, n- or i-propoxycarbonyl-, N-or propargyloxycarbonyl-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- Methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, Methylamino, ethylamino, or n- or i-propylamino, or in each case optionally cyano-, carboxyl-, fluorine-, chlorine-, bromine-, In each case optionally fluorine- and / or chlorine-, methoxy- and / or ethoxycarbonyl-substituted ethenyl, propenyl, ethynyl, propynyl, propenyloxy or propynyloxy, -, or ethoxy-substituted acetylamino, propionylamino, methoxycarbonylamino, ethoxycarbonylamino, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i methylsulfonylamino, N, N-bis-ethylsulfonylamino, N-ethylsulfonyl-N-methylsulfonylamino, N-methyl N-propylsulfonylamino, N-methylsulfonyl-N-propylsulfonylamino, N-acetyl-N-methylsulfonylamino, N- , 2-dimethylpropanoyl) -N-ethylsulfonylamino, N- (2-methylpropanoyl) -N-ethylsulfonylamino, Nn-butyroyl- N-methylsulfonyl Amino, Ns-butyroyl-N-methylsulfonylamino, Nt-butyroyl-N-methylsulfonylamino, N-acetyl- , N-butyroyl-N-ethylsulfonylamino, N-butyroyl-N-ethylsulfonylamino, Or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- or tri Fluoromethoxy-substituted N-phenylcarbonyl-N-methylsulfonylamino, N-phenylcarbonyl-N-ethylsulfonylamino, N-thienylcarbonyl-N-methylsulfonylamino or N-thienyl RTI ID = 0.0 > (I) < / RTI > representing carbonyl-N-ethylsulfonylamino.
[4" claim-type="Currently amended] The composition according to claim 1, wherein the active compound of Group 1
R ¹ represents amino,
R ² represents trifluoromethyl,
R ³ represents hydrogen, chlorine or methyl,
R ⁴ represents fluorine,
R < ⁵ > represents cyano or thiocarbamoyl,
R ⁶ is in each case optionally fluorine- and / or chlorine-substituted methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t- Amino, N, N-bis-methylsulfonylamino, N, N-bis-ethylsulfonylamino, N-ethylsulfonyl-N-methylsulfonylamino, N-methylsulfonyl- N-methylsulfonylamino, N-acetyl-N-methylsulfonylamino, N- (2,2-dimethylpropanoyl) -N -N-ethylsulfonylamino, N- (2-methylpropanoyl) -N-ethylsulfonylamino, N, N-butyroyl- Methylsulfonylamino, N-methoxyacetyl-N-methylsulfonylamino, N-acetyl-N-ethylsulfonylamino, N- Propionyl-N-ethylsulfonylamino, N-butyroyl-N-ethylsulfonylamino, Ni-butyroyl N-ethylsulfonylamino, N-methoxyacetyl-N-ethylsulfonylamino, N-methoxyacetyl-N-ethylsulfonylamino, In each case optionally substituted with one or more substituents selected from the group consisting of cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- or trifluoromethoxy- N-phenylcarbonyl-N-methylsulfonylamino, N-phenylcarbonyl-N-ethylsulfonylamino, N-thienylcarbonyl-N-methylsulfonylamino or N-thienylcarbonyl- RTI ID = 0.0 > (I) < / RTI > representing sulfonylamino.
[5" claim-type="Currently amended] The composition according to claim 1, wherein the active compound of Group 1
R ¹ represents methyl,
R ² represents trifluoromethyl,
R ³ represents hydrogen, chlorine or methyl,
R ⁴ represents fluorine,
R ⁵ represents thiocarbamoyl,
R ⁶ is in each case optionally fluorine- and / or chlorine-substituted methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t- Amino, N, N-bis-methylsulfonylamino, N, N-bis-ethylsulfonylamino, N-ethylsulfonyl-N-methylsulfonylamino, N-methylsulfonyl- N-methylsulfonylamino, N-acetyl-N-methylsulfonylamino, N- (2,2-dimethylpropanoyl) -N -N-ethylsulfonylamino, N- (2-methylpropanoyl) -N-ethylsulfonylamino, N, N-butyroyl- Methylsulfonylamino, N-methoxyacetyl-N-methylsulfonylamino, N-acetyl-N-ethylsulfonylamino, N- Propionyl-N-ethylsulfonylamino, N-butyroyl-N-ethylsulfonylamino, Ni-butyroyl N-ethylsulfonylamino, N-methoxyacetyl-N-ethylsulfonylamino, N-methoxyacetyl-N-ethylsulfonylamino, In each case optionally substituted with one or more substituents selected from the group consisting of cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- or trifluoromethoxy- N-phenylcarbonyl-N-methylsulfonylamino, N-phenylcarbonyl-N-ethylsulfonylamino, N-thienylcarbonyl-N-methylsulfonylamino or N-thienylcarbonyl- RTI ID = 0.0 > (I) < / RTI > representing sulfonylamino.
[6" claim-type="Currently amended] The composition according to claim 1, wherein the active compound of Group 1
R ¹ represents amino or methyl,
R ² represents trifluoromethyl,
R ³ represents hydrogen, chlorine or methyl,
R ⁴ represents hydrogen, fluorine or chlorine,
R < ⁵ > represents cyano, thiocarbamoyl or chlorine,
R ⁶ represents a carboxyl, carbamoyl, thiocarbamoyl, hydroxyl, mercapto, amino, fluorine, chlorine or bromine or in each case optionally cyano-, carboxyl-, hydroxyl-, methoxy-, ethoxy -, acetyl-, propionyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, allyloxycarbonyl- or propargyloxycarbonyl-substituted methyl, ethyl, n-or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, N-propyl, n-propyl, n-propyl, n-butoxy, n-butoxy, - (2,2-dimethylpropanoyl) -N-ethylsulfonylamino or N- (2-methylpropanoyl) -N-ethylsulfonylamino, or in each case optionally cyano-, -, fluorine-, chlorine-, bromine-, methoxycarbonyl- and / or ethoxycarbonyl-substituted ethenyl, propenyl, ethynyl, propynyl, propenyloxy or propynyloxy RTI ID = 0.0 > I) < / RTI >
[7" claim-type="Currently amended] The composition according to claim 1, wherein the active compound of Group 1
2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoro (2H) -pyrimidinyl) -benzoate, < RTI ID = 0.0 >
(2H) -pyrimidinyl) -2 - [(1-methyl < RTI ID = 0.0 & -2-propynyl) -oxy] -benzonitrile,
4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- -Phenyl] -N- (2,2-dimethylpropanoyl) -1-ethanesulfonamide,
4-trifluoromethyl-3,6-dihydro-1 (2H) -pyrimidinyl) -2-cyano- - phenyl] -N- (4-methoxybenzoyl) -ethanesulfonamide,
Dihydro-1 (2H) -pyrimidinyl) -2-cyano-4-fluoro < / RTI > -Phenyl] -N- (2-thienylcarbonyl) -1-ethanesulfonamide and
2- (Ethylsulfonylamino) -5- fluoro-4- [3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro- 1 (2H) -pyrimidinyl ] -Benzene carbothioamide. ≪ / RTI >
[8" claim-type="Currently amended] The compound according to any one of claims 1 to 7,
But are not limited to, acetonitrile, acetonitrile, acetonitrile, acetonitrile, acetonitrile, acetonitrile, acetonitrile, acetonitrile, But are not limited to, methanamide, diuron, EPTC, fenoxaprop-P-ethyl, pentrazamid, flucarbazone-sodium, flupenase, flumetsulam, glufosinate-ammonium, glyphosate-isopropylammonium, But are not limited to, cholesterol, chymotrypsin, imazacin, imazetapyr, isoxaflutol, mesotrione, metolachlor, S-metolachlor, metribuzin, nicosulfuron, But are not limited to, sodium, limsulfuron, simajin, sulfomethuron-methyl, sulcotrione, sulfentrazone, sulfosate, tbutyl azine, thifensulfuron-methyl, trifluralin and 4- [4,5- 2 - [(ethylsulfonyl) amino] -5-fluoro-benzene < / RTI > ≪ / RTI > wherein said herbicidal composition comprises at least one compound selected from the group consisting of a butyrolactone and a butyrolaide.
[9" claim-type="Currently amended] 9. Compounds according to any one of claims 1 to 8, wherein as active compounds of group 3
1-methyl-hexyl 5-chloro-quinoxaline-8-oxy-acetate (cloquintocet-mexyl)
Ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazole carboxylate (isoxadifen-ethyl),
Diethyl 1- (2,4-dichloro-phenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-
4-aza-spiro [4.5] -decane (AD-67), 4-dichloroacetyl-
1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo [1,2-a] pyrimidin-6 (2H) -one (BAS-
4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l, 4- benzoxazine (berdoxacor)
2,2-dichloro-N, N-di-2-propenyl-acetamide (dichloride),
3-dichloroacetyl-5- (2-furanyl) -2,2-dimethyl-oxazolidine (furilazole, MON-13900) and
3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148) group.
[10" claim-type="Currently amended] Use of a composition according to any one of claims 1 to 9 for the control of unwanted plants.
[11" claim-type="Currently amended] A method for controlling unwanted plants characterized by the action of a composition according to any one of claims 1 to 9 on undesired plants and / or their habitats.
[12" claim-type="Currently amended] A process for preparing a herbicidal composition characterized by mixing the composition according to any one of claims 1 to 9 with a surfactant and / or an extender.

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同族专利:

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公开号 | 公开日

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EP1278413A2|2003-01-29|

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US6734139B1|2004-05-11|

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US20040171488A1|2004-09-02|

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BR0016120A|2002-08-27|

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MXPA02005471A|2003-02-12|

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DE19958381A1|2001-06-07|

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AU2669101A|2001-06-12|

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WO2001039597A3|2002-10-31|

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WO2001039597A2|2001-06-07|

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PL362904A1|2004-11-02|

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CN1407854A|2003-04-02|

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JP2003517473A|2003-05-27|

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CO5231186A1|2002-12-27|

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CA2392107A1|2001-06-07|

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AR026665A1|2003-02-19|

引用文献:

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公开号 | 申请日 | 公开日 | 申请人 | 专利标题

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法律状态:
1999-12-03|Priority to DE19958381.1

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1999-12-03|Priority to DE19958381A

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2000-11-21|Application filed by 빌프리더 하이더, 바이엘 악티엔게젤샤프트

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2000-11-21|Priority to PCT/EP2000/011833

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2002-07-13|Publication of KR20020059758A

优先权:

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申请号 | 申请日 | 专利标题

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DE19958381.1|1999-12-03|

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DE19958381A|DE19958381A1|1999-12-03|1999-12-03|Herbicides based on N-aryl-uracils|

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PCT/EP2000/011833|WO2001039597A2|1999-12-03|2000-11-21|N-aryl-uracile-based herbicides|