| 摘要 |
<p>#CMT# #/CMT# A crop protection composition comprises at least one substituted 1H-pyridin-2-one compound and optionally formulation auxiliaries. #CMT# : #/CMT# 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). #CMT#[Image]#/CMT# #CMT#ACTIVITY : #/CMT# 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. #CMT#MECHANISM OF ACTION : #/CMT# None given. #CMT#USE : #/CMT# For protecting useful plants against phytotoxic side effects of agrochemicals; for selective control of harmful plants in crops of useful plants (claimed) e.g. corn, rice or cereals; as useful-plant protecting agents for reducing or preventing harmful effects of agrochemicals on the useful plants; as safeners for reducing phtotoxic actions of agrochemicals e.g. pesticide such as herbicide. #CMT#ADVANTAGE : #/CMT# The compound (I) with agrochemicals which, applied on their own (preferably post-emergence method), causes damage to the useful plants, optionally in the presence of formulation auxiliaries. The compound (I) protects useful plants against phytotoxic side effects of agrochemicals; provides selective control of harmful plants in crops of useful plants. #CMT#AGRICULTURE : #/CMT# Preferred Method: In the method (M1), the application of the compound (I) involves: treating the plant seeds or seed of the plants by post- or pre-emergence method. The method (M2) involves: treating the seed of the plants with the compound (I) or it salt and applying the herbicide after sowing by the pre-emergence method or by the post-emergence method. #CMT#[Image]#/CMT# #CMT#ORGANIC CHEMISTRY : #/CMT# Preparation (Claimed): Preparation of the compound (I) involves: (1) process (A): reacting a carboxylic acid of formula (II) with an amine of the formula NH(R 3)(R 4) (III) or its salt'; (2) process (B): reacting a carboxylic ester of formula (IV) with the amine (III); (3) process (C): reacting a carbonyl halide or a carboxylic anhydride of formula (V) with an amine (III); or (4) reacting a compound of formula R 1-C(O)-CH=CH-OAlkyl (VI) with malonamide to obtain compound (I) (where R 1 and R 2 are H). Alkyl : alkyl radical; Hal : halogen atom or an acyloxy radical. #CMT#DEFINITIONS : #/CMT# Preferred Definitions: R 1 : (i)-(xi); R 2,R 3,R 4 : H. #CMT#ADMINISTRATION : #/CMT# The compound (I) is applied at a rate of 0.001-10 (preferably 0.01-1, especially 0.05-0.5) kg/hectare. For seed dressing, the compound (I) is applied at a rate of 0.005-20 (preferably 0.01-10, especially 0.05-5) g. #CMT#SPECIFIC COMPOUNDS : #/CMT# 2173 Compounds are disclosed e.g. N-cyclobutyl-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide (IA); 6-(chloro(difluoro)methyl]-N-(2-methoxyethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide; methyl N-{6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridin-3-yl}carbonyl)glycinate; N-(1-methylpropyl)-2-oxo-6-(pentafluoroethyl)-1,2-dihydropyridine-3-carboxamide; and 2-oxo-6-(pentafluoroethyl)-1,2-dihydropyridine-3-carboxamide. #CMT#[Image]#/CMT# #CMT#EXAMPLE : #/CMT# At 5[deg] C, trifluoroacetic anhydride (79.9 g) dissolved in trichloromethane (100 ml) were added with stirring to a mixture of pyridine (29.9 g) and butyl vinyl ether (50.0 g) in trichloromethane (200 ml). After the addition, stirring was continued at room temperature for another 15 hours. Water (300 ml) were then added to the mixture, and the organic phase was separated off, dried and concentrated. After work up, 4-butoxy-1,1,1-trifluorobut-3-en-2-one (A1) was obtained. Sodium (2.15 g) was dissolved in methanol (300 ml), (A1) (15.3 g) and methyl malonate-monoamide (9.13 g) were added and the mixture was heated under reflux for 18 hours. The mixture was concentrated, and the residue was taken up in water and washed with dichloromethane. After workup, methyl 2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylate (A2) was obtained. At room temperature, (A2) (4.73 g) was dissolved in methanol (45 ml) and water (15 ml), lithium hydroxide monohydrate (1.80 g) were added and the mixture was then heated under reflux for 2 hours. The mixture was concentrated to 15 ml and then washed with dichloromethane and the aqueous phase was adjusted to pH 2 by addition of 2N hydrochloric acid. After work up, 2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylic acid (A3) was obtained. (A3) (600 mg) was dissolved in tetrahydrofuran (5 ml), N,N-carbonyldiimidazole (658 mg) were added and the mixture was heated initially at room temperature for 30 minutes and then under reflux for 30 minutes. A solution of cyclobutylamine (247 mg) in tetrahydrofuran (5 ml) was then added dropwise, and the mixture was heated under reflux for a further 2 hours. The solution was evaporated to dryness and then taken up in ethyl acetate, washed with 1 N hydrochloric acid and water, dried and concentrated. After workup, N-cyclobutyl-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide (160 mg; 19%) was obtained.</p> |
