| 摘要 |
<p>#CMT# #/CMT# 4-Phenylpyridazinone compounds (I) and their salts are new. #CMT# : #/CMT# 4-Phenylpyridazinone compounds of formula (I) and their salts are new. A : H, 3-6C-cycloalkyl or 1-6C-alkyl (substituted by n residues of halo, 3-6C-cycloalkyl, phenyl or halophenyl); B1 : 3-6C-cycloalkyl or 1-6C-alkyl (substituted by m residues of halo, 3-6C-cycloalkyl, phenyl or halophenyl); m, n : 0-3, with the proviso that m and n are not simultaneously 0; G : H, C(=O)R1, C(=L)MR2, SO 2R3, P(=L)R4R5, C(=L)NR6R7, E or R8; E : metal ion equivalent or ammonium ion; L, M : O or S; R1 : 1-6C-alkyl, 2-6C-alkenyl, 1-4C-alkoxy-1-6C-alkyl, di-1-4C-alkoxy-1-6C-alkyl or 1-4C-alkylthio-1-6C-alkyl (all substituted by n halo), 3-6C-cycloalkyl, phenyl, phenyl-1-4C-alkyl, heteroaryl, phenoxy-1-4C-alkyl or heteroaryloxy-1-4C-alkyl (all substituted by n residues of halo, 1-4C-alkyl or 1-4C-alkoxy) or completely saturated 3-6 membered ring comprising 3-5C and 1-3 heteroatoms of O, S or N, where the ring is substituted by n residues of halo, 1-4C-alkyl or 1-4C-alkoxy; R2 : 1-6C-alkyl, 2-6C-alkenyl, 1-4C-alkoxy-1-6C-alkyl or di-1-4C-alkoxy-1-6C-alkyl (all substituted by n halo), 3-6C-cycloalkyl, phenyl or benzyl (all substituted by n residues of halo, 1-4C-alkyl or 1-4C-alkoxy); R3-R5 : 1-6C-alkyl, 1-4C-alkoxy, N-1-6C-alkylamino, N,N-di-1-6C-alkylamino, 1-4C-alkylthio, 2-4C-alkenyl or 3-6C-cycloalkylthio (all substituted by n halo), phenyl, benzyl, phenoxy or phenylthio (all substituted by n residues of halo, 1-4C-alkyl or 1-4C-alkoxy); either R6, R7 : 1-6C-alkyl, 3-6C-cycloalkyl, 2-6C-alkenyl, 1-6C-alkoxy or 1-4C-alkoxy-1-6C-alkyl (all optionally substituted by n halo), phenyl or benzyl (both substituted by n residues of halo, 1-4C-alkyl or 1-4C-alkoxy) or H; or R6NR7 : 3-6 membered ring comprising 2-5C and 0 or 1 O or S; either X : H, 1-6C-alkyl or 3-6C-cycloalkyl; Y1 : halo, cyano, nitro, halo-1-6C-alkyl, halo-1-6C-alkoxy, 3-6C-cycloalkyl, 1-6C-alkoxy or phenyl (substituted by n halo atoms); and Z : H, halo, cyano, nitro, 1-6C-alkyl, halo-1-6C-alkyl, halo-1-6C-alkoxy, 3-6C-cycloalkyl or phenyl (substituted by n halo atoms); or X : halo, cyano, nitro or 1-6C-alkyl, 3-6C-cycloalkyl, 1-6C-alkoxy or phenyl (all substituted by n halo atoms); and Y1, Z : H, halo, cyano, nitro, 3-6C-cycloalkyl or 1-6C-alkyl, 1-6C-alkoxy or phenyl (all substituted by n halo atoms); and R8 : not defined. Independent claims are included for: (1) a herbicidal composition comprising (I); (2) substituted phenyl compounds of formula (II); and (3) substituted phenyl-acetic acid hydrazide compounds of formula (III). R9 : 1-6C-alkyl. #CMT#[Image]#/CMT# #CMT#[Image]#/CMT# #CMT#ACTIVITY : #/CMT# Insecticide; Herbicide; Plant Protectant. The herbicidal activity of (I) was tested against Echinochloa crus galli, Stellaria media and Veronica persica. The results showed that carbonic acid 5-(2-chloro-6-ethyl-phenyl)-1-cyclopropylmethyl-3-methyl-6-oxo-1,6-dihydro-pyridazin-4-yl ester ethyl ester (320 g/hectare) exhibited herbicidal activity of 90%. #CMT#MECHANISM OF ACTION : #/CMT# None given. #CMT#USE : #/CMT# (I) are useful for combating unwanted plants by applying (I) on the plant or their habitat. (I) are useful to control unwanted plants in crops of useful plants, where the useful plants are transgenic useful plants. (I) are useful as insecticide (all claimed). (I) are useful in plant protecting agents, preferably herbicides for selective control of weeds and grass weeds in culture crops. #CMT#ADVANTAGE : #/CMT# (I) exhibit reduced application rates. (I) provide better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased blooming power, facilitated harvesting, acceleration of maturity, higher yields, higher quality and/or higher nutritional value harvest products. #CMT#ORGANIC CHEMISTRY : #/CMT# Preparation (Disclosed): Preparation of (I) comprises reacting 2H-pyridazin-3-one compounds of formula (a) with phenyl compounds of formula (b) in the presence of catalyst e.g. palladium-salt or -complex, and in the presence of base e.g. sodium- or potassium-carbonate to give (I) (where G is R8). Z : Br or I; and Q : trialkyl-tin, magnesium halide or boronic acid or its ester. #CMT#[Image]#/CMT# #CMT#DEFINITIONS : #/CMT# Preferred Definitions: A : cyclopropyl, cyclopropylmethyl, benzyl, 2-chlorophenylmethyl, 3-chlorophenylmethyl or 4-chlorophenylmethyl; B1 : H, 2,2-difluoroethyl, cyclopropyl, cyclopropylmethyl, benzyl, 2-chloro-phenylmethyl, 3-chloro-phenylmethyl or 4-chloro-phenylmethyl; E : Na +>, K +>, (Mg 2> +>) 1 / 2, (Ca 2> +>) 1 / 2, (CH 3) 4N +> or NH 4 +>; L, M : O; R1 : 1-6C-alkyl or 3-6C-cycloalkyl; R2 : 1-6C-alkyl, 3-6C-cycloalkyl or benzyl; R3-R5 : 1-6C-alkyl, phenyl or benzyl; R6, R7 : H, 1-6C-alkyl, phenyl or benzyl; and either X : H, methyl or ethyl; Y1 : F, Br, Cl, I, cyano, nitro, cyclopropyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, phenyl or halophenyl; and Z : H, F, Br, Cl, I, methyl, ethyl, methoxy, ethoxy, trifluoromethyl or cyclopropyl; or X : F, Br, Cl, I, cyano, nitro, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy or cyclopropyl; Y1 : H, F, Br, Cl, I, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy or cyclopropyl; and Z : H, F, Br, Cl, I, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, cyclopropyl, chlorophenyl or fluorophenyl. #CMT#ADMINISTRATION : #/CMT# Application of (I) is 0.001-1 kg/hectare, preferably 0.005-750, g/hectare, by spraying, atomizing or dusting. #CMT#SPECIFIC COMPOUNDS : #/CMT# 15030 Compounds (I) are disclosed e.g. 2-cyclobutyl-4-(2,4-dichloro-phenyl)-5-hydroxy-6-methyl-2H-pyridazin-3-one of formula (Ia), 6-cyclopentyl-4-(2,4-dichloro-6-ethyl-phenyl)-5-hydroxy-2-methyl-2H-pyridazin-3-one, 2-benzyl-4-(2,4-dichloro-6-ethyl-phenyl)-5-hydroxy-6-methyl-2H-pyridazin-3-one, 4-(2-chloro-4,6-dimethyl-phenyl)-2-cyclopropylmethyl-5-hydroxy-6-methyl-2H-pyridazin-3-one and 6-cyclopentyl-4-(2,6-dichloro-phenyl)-5-hydroxy-2-methyl-2H-pyridazin-3-one. 30 Compounds (II) are disclosed e.g. 2-{benzyl-[2-(2,3,6-trifluoro-phenyl)-acetyl]-hydrazono}-propionic acid ethyl ester of formula (IIa), 2-{cyclopropylmethyl-[2-(2,4-dibromo-6-methyl-phenyl)-acetyl]-hydrazono}-propionic acid methyl ester, 2-{benzyl-[2-(2,4,6-trichloro-phenyl)-acetyl]-hydrazono}-propionic acid ethyl ester, 2-{benzyl-[2-(2-chloro-6-fluoro-3-methyl-phenyl)-acetyl]-hydrazono}-propionic acid ethyl ester and 2-{cyclopropylmethyl-[2-(2,6-dichloro-phenyl)-acetyl]-hydrazono}-propionic acid methyl ester. #CMT#[Image]#/CMT# #CMT#[Image]#/CMT# #CMT#EXAMPLE : #/CMT# A solution of dimethylformamide (10 ml) and 2-cyclobutyl-{[2-(2, 4-dichlorophenyl)-acetyl]-hydrazono}-propionic acid ethyl ester (2 mmole) was added dropwise to a solution of potassium tert-butylate (0.331 g, 2 equivalent) in dimethylformamide (10 ml) at less than 0[deg] C for 2 hours, and stirred at 0[deg] C for 90 minutes. Then 0.5N cold hydrochloric acid (100 ml) was added to the reaction mixture. The reaction mixture was concentrated under reduced pressure and the mixture was added with water (50 ml). The mixture was extracted twice with ethyl acetate (50 ml). The obtained organic phases were dried and worked up to give 2-cyclobutyl-4-(2,4-dichloro-phenyl)-5-hydroxy-6-methyl-2H-pyridazin-3-one.</p> |
