Patent EP-1987717-A1 (EP)
IPC: C07D413/06
Filed: 2007-04-30
Abstract: A crop protection composition comprises at least one substituted 1H-pyridin-2-one compound and optionally formulation auxiliaries. A crop protection composition comprises at least one substituted 1H-pyridin-2-one compound of formula (I) or its salt and optionally formulation auxiliaries. R 1 : (1-6C)-haloalkyl radical, or group of formluae CF 2C 1 (i), CF 2H (ii), CF 2CF 3 (iii), CF 2CF 2H (iv), CF 2CF 2Cl (v), CFClCF 3 (vi), CFHCF 3 (vii), CF(CF 3) 2 (viii), CH(CF 3) 2 (ix), CF 2CF 2CF 3 (x), or C(CH 3) 2F (xi); R 2 : H or halo; R 3 : (1-16C)-alkyl, (2-16C)-alkenyl or (2-16C)-alkynyl (all optionally substituted by t 1) or H; t 1 : (3-6C)-cycloalkyl, (4-6C)-cycloalkenyl, (3-6C)-cycloalkyl or (4-6C)-cycloalkenyl (both condensed at one side of the ring to a 4- to 6-membered optionally saturated carbocyclic ring) (all optionally substituted by t 2), or t 3; t 3 : (3-6C)-cycloalkyl (optionally substituted by phenyl or heterocyclyl (both optionally substituted)), halo, OH, cyano, (1-4C)-alkoxy, (1-4C)-haloalkoxy, (1-4C)-alkylthio, (1-4C)-alkylamino, di[(1-4C)-alkyl]-amino, [(1-4C)-alkoxy]-carbonyl or [(1-4C)-haloalkoxy]-carbonyl; t 2 : t 3, 1-4C alkyl, or 1-4C haloalkyl; R 4 : (1-16C)-alkyl, (2-16C)-alkenyl or (2-16C)-alkynyl (all optionally substituted by t 1); R 3 : (1-4C)-alkoxy, (2-4C)-alkenyloxy, (2-6C)-alkynyloxy or (2-4C)-haloalkoxy; R 4 : H or (1-4C)-alkyl;or NR 3R 4 : four- to eight-membered heterocyclic ring which, in addition to the nitrogen atom, may also comprise further hetero ring atoms (optionally substituted by halo, cyano, nitro, (1-4C)-alkyl, (1-4C)-haloalkyl, (1-4C)-alkoxy, (1-4C)-haloalkoxy and (1-4C)-alkylthio); or -N=CR 5-NR 6R 7; R 5 : H or (1-6C)-alkyl; R 6,R 7 : H or (1-4C)-alkyl;or NR 6R 7 : five- to seven-membered heterocyclic ring. Provided that when R 1=(1-6C)-haloalkyl radical, then R 2 is halo, R 3 and R 4 are H; when R 1 is (i)-(xi), then R 2, R 3 and R 4 are hydrogen. Independent claims are included for the following: (1) method (M1) for protecting useful plants against phytotoxic side effects of agrochemicals involves: applying the compound (I) or its salt, before, after or simultaneously with the agrochemicals to the plants, parts of the plants, the plant seeds or seed of the plants; (2) a method (M2) for selective control of harmful plants in crops of useful plants involving: applying the compound (I) before, after or simultaneously with at least one herbicide to the plants, parts of plants, plant seeds or seed of the plants; (3) substituted 1H-pyridin-2-one compound formula (I) (in which R 3 is (1-16C)-alkyl, (2-16C)-alkenyl or (2-16C)-alkynyl (all optionally substituted by t 1') or H; t 1' is (3-6C)-cycloalkyl, (4-6C)-cycloalkenyl, (3-6C)-cycloalkyl or (4-6C)-cycloalkenyl (both condensed at one side of the ring to a 4- to 6-membered optionally saturated carbocyclic ring) (all optionally substituted by t 2'), or t 3'; t 3' is halo, OH, cyano, (1-4C)-alkoxy, (1-4C)-haloalkoxy, (1-4C)-alkylthio, (1-4C)-alkylamino, di[(1-4C)-alkyl]-amino, [(1-4C)-alkoxy]-carbonyl or [(1-4C)-haloalkoxy]-carbonyl and t 2' is (3-6C)-cycloalkyl (optionally substituted by phenyl or heterocyclyl (both optionally substituted)) or t 3'); and (4) preparation of the compound (I). [Image] ACTIVITY : Plant protectant; Plant growth inhibitor. Post-Emergence Herbicide action and safener action was carried out as follows: Seeds or rhizome pieces of monocotyledonous and dicotyledonous harmful plants and crop plants were placed in sandy loam soil in plastic pots, covered with soil and cultivated in the greenhouse under good growth conditions. Three weeks after sowing, the test plants were treated at the three-leaf stage. Mesosulfuron-methyl (herbicide)/N-cyclobutyl-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide (test compound) (safener) formulated as emulsion concentrates, and in parallel tests the individual active compounds formulated in a corresponding manner, were sprayed at various dosages at a water application rate of 300 l/ha (converted) onto the green parts of the plants, and, after the test plants were left to stand in the greenhouse for 2 to 3 weeks under optimum growth conditions, the effect of the preparations was scored visually in comparison to untreated controls. The test showed that the test compound as safener in combination with herbicide, in a herbicide: safener ratio of 2:1-1:20, considerably reduces the damage caused by the herbicide to crop plants such as barley compared to the application of the individual herbicides without safener, such that from 30% up to 100% less damage to the crop plant was observed. At the same time, the action of the herbicide against economically important harmful plants was not, or not essentially, adversely affected, so that good herbicidal post-emergence action against a broad spectrum of weed grasses and broad-leaved weeds was achieved. MECHANISM OF ACTION : None given.