Abstract:
PROBLEM TO BE SOLVED: To provide an intermediate of an isoxazolin-3-ylacyl benzene useful as an agricultural chemical, and a new method for producing the intermediate. SOLUTION: A benzaldoxime derivative represented by formula III (wherein R 1 is a 1-6C alkyl group) can be obtained by reacting a corresponding methylbenzene derivative with an organic nitrite in an aprotic polar solvent in the presence of a base at lower temperature than -20°C. COPYRIGHT: (C)2010,JPO&INPIT
Abstract:
The present invention relates to a method for producing 2- (aminomethylidene)-4,4dihalo-3-oxobutyric acid esters of the formula (I), where R1, R2, R3 are C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C3-C10-cycloalkyl or benzyl and/or R2 together with R3 and the nitrogen atom, to which both radicals are bound, are a heterocyclic radical, wherein a corresponding 3-aminoacrylic acid ester is reacted with a halogen-substituted acetyl fluoride in the presence of at least one alkali or earth alkali metal fluoride. The invention also relates to the further reaction of halogen-substituted 2-(aminomethylidene)-3-oxobutyric acid esters of the formula (1) into halomethyl-substituted pyrazole-4-ylcarboxylic acids and the esters thereof.
Abstract:
The invention relates to piperazine compounds of the following defined general formula (I) and to their use as herbicides. The invention also relates to crop protection agents and to a method for combating undesired plant growth. In formula (I): R1 is selected from halogen, cyano, nitro, Z-C(=O)-R12, phenyl and a 5- or 6-membered heterocyclic group that has 1, 2, 3 or 4 heteroatoms, selected from O, N and S as ring atoms, wherein phenyl and the heterocyclic group are unsubstituted or have 1, 2, 3 or 4 substituents R1a; Z stands for a covalent bond or a CH2 group; R12 represents hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6alkenyl, C5-C6 cycloalkenyl, C2-C6alkynyl and similar; R2 represents hydrogen, halogen, nitro, cyano, C1-C4alkyl, C1-C4 haloalkyl, C2- C4 alkenyl, C1-C4 alkoxy, C1-C4haloalkoxy, benzyl or a group S(O) nR21, wherein R21 stands for C1-C4 alkyl or C1-C4 haloalkyl and n stands for 0, 1 or 2; R3 represents hydrogen or halogen; R4 represents C1-C4 alkyl, C3- C4 alkenyl or C3-C4 alkynyl; R5 represents hydrogen, C1-C4alkyl, C3-C4 alkenyl, C3-C4 alkynyl or a group (=O)R51, wherein R51 stands for hydrogen, C1-C4alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy; R6 stands for C1-C4alkyl, C1-C4 hydroxy alkyl or C1-C4haloalkyl; R7, R8 stand, independently of one another, for hydrogen, OH, C1-C4 alkoxy, C1-C4 haloalkyoxy, C1-C4 alkyl or C1-C4 haloalkyl; R9, R10 are selected, independently of one another, from hydrogen, halogen, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C1-C4 alkoxy and C1-C4 haloalkoxy; and R11 represents hydrogen or C1-C4 alkyl. The invention also relates to the agriculturally suitable salts of said compounds.
Abstract:
The present invention relates to a method for preparing 4-chloro-, 4-bromo- or 4- iodobenzaldehyde oximes and phenyl-substituted isoxazoline compounds prepared from these oximes.
Abstract:
A process for reacting chemical compounds comprising the step of oxidizing a compound of formula (II) wherein R1 and R2 are halogen, and R3 is -(C1-C4) alkyl, in the presence of a peroxy reagent to obtain a compound of formula (III).
Abstract:
The invention relates to piperazine compounds of the following defined general formula (I) and to their use as herbicides. The invention also relates to crop protection agents and to a method for combating undesired plant growth. In formula (I), the variables are defined as follows: R1 is selected from halogen, cyano, nitro, Z-C(=O)-R11, phenyl and a 5- or 6-membered heterocyclic group that has 1, 2, 3 or 4 heteroatoms, selected from O, N and S as ring atoms, wherein phenyl and the heterocyclic group are unsubstituted or have 1, 2, 3 or 4 substituents R1a; Z stands for a covalent bond or a CH2 group; R11 represents hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C5-C6 cycloalkenyl, C2-C6 alkynyl and similar; R2 represents hydrogen, halogen, nitro, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C2- C4 alkenyl, C1-C4 alkoxy, C1-C4 haloalkoxy, benzyl or a group S(O) nR21, wherein R21 stands for C1-C4 alkyl or C1-C4 haloalkyl and n stands for 0, 1 or 2; R3 represents hydrogen or halogen; R4 represents C1-C4 alkyl, C3- C4 alkenyl or C3-C4 alkynyl; R5 represents hydrogen, C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl or a group (=O)R51, wherein R51 stands for hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy; R6 stands for C1-C4 alkyl, C1-C4 hydroxy alkyl or C1-C4 haloalkyl; R7, R8 stand, independently of one another, for hydrogen, OH, C1-C4 alkoxy, C1-C4 haloalkyoxy, C1-C4 alkyl or C1-C4 haloalkyl; R9, R10 are selected, independently of one another, from hydrogen, halogen, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C1-C4alkoxy and C1-C4 haloalkoxy.
Abstract:
The present invention relates to sulfonamide compounds of formula (I) wherein R1 is H, halogen, CN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C2-C6-alkenylthio, C2-C6-alkynylthio, C1-C6-haloalkyl or C1-C6-haloalkoxy; R2 and R3 are H, halogen, CN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C2-C6-alkenylthio, C2-C6-alkynylthio, C1-C6-haloalkyl or C1-C6-haloalkoxy; or R2 together with R3 form a fused 5 or 6-membered carbocycle or heterocycle; R4 is halogen, CN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkyl, C1-C6-haloalkoxy, C1-C6-haloalkylthio, C1-C6-haloalkylsulfinyl or C1-C6-haloalksulfonyl; n is 0, 1, 2 or 3; R5 is phenyl or a 5- or 6-membered heterocycle; X is O or NRx, wherein Rx is H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylcarbonyl or C1-C6-alkylcarbonyloxy; Y is N or C(Ry), wherein Ry is H, halogen, CN, C1-C6-alkyl,C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C3-7-cycloalkyl- C1-C4-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C2-C6-alkenylthio, C2-C6-alkynylthio, C1-C6-haloalkyl and C1-C6-haloalkoxy; and Z is a chemical bond, O or N(Rz), wherein Rz is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C1-C6-alkylcarbonyl or C1-C6-alkylcarbonyloxy; as well as to the N-oxides and salts thereof. These compounds are useful for combating animal pests. The invention also relates to a process for the preparation of these compounds and to intermediate compounds used in said process. The invention further relates to a method for controlling animal pests by using the compounds of formula (I), the N-oxides or the salts thereof, to plant propagation material and to an agricultural and veterinary composition comprising said compounds, the N-oxides or the salts thereof.
Abstract:
This invention relates to a process for preparing substituted phenylhydrazines of the formula I wherein R has the meaning as indicated in the description, comprising reacting a dichlorofluorobenzene of the formula Il with a hydrazine source selected from hydrazine, hydrazine hydrate and acid addition salts of hydrazine and optionally being carried out in the presence of at least one organic solvent.
Abstract:
The present invention relates to a method for preparing 1,3-substituted pyrazol compounds of formula (I), where X stands for a group CX1X2X3, with X1, X2 and X3 being hydrogen, fluorine or chlorine, independently of one another, R1 being an C1-C4 alkyl or cyclopropyl, and R2 being hydrogen, CN or a group CO2R2a, where R2a stands for C1-C6 alkyl in particular, comprising the following steps: i) reacting a compound of formula II with a hydrazone of formula (III), wherein in formula (II) the variables X and R2 have the same meaning as indicated for formula (I), Y stands for oxygen, a group NRy1 or a group [NRy2Ry3]+Z- , R3 stands for OR3a or a group NR3bR3c, and wherein in formula (III) the variable R1 has the same meaning as indicated for formula (I), R4 and R5 stand for hydrogen, C1-C6 alkyl, alternatively substituted phenyl, independent of one another, wherein at least one of the radicals R4 or R5 is different from hydrogen and where R4 and R5 can also stand for a 5 to 10-membered saturated carbocycle together with the carbon atom connected thereto; treatment of the reaction product obtained thereby with an acid in the presence of water.
Abstract:
The invention relates to a method for producing 3-difluoromethyl-substituted pyrazole compounds of formula (I), wherein R1 represents H, halogen, nitro, C1-C8 alkyl, C1-C8 haloalkyl, C3-C8 cycloalkyl, phenyl, naphthyl, hetaryl, cyano, -C(=O)-OR1a, -C(=O)-NR1bR1c, -C(=O)-SR1d or -C(=S)-SR1 e; R2 represents H, C1-C4 alkyl, benzyl or phenyl; R3 represents H, halogen, C1-C8 alkoxy, C1-C8 haloalkoxy, C3-C8 cycloalkoxy, C2-C8 alkenyloxy, C1-C8 alkylthio, C1-C8 haloalkylthio, C3-C8 cycloalkylthio or C2-C8 alkenylthio; to compounds of formula (II.a) or (II.b), wherein R1 and R3 have one of the above definitions; R4 represents halogen, -OR4a, -SR4a , -O-SO2-R4a or a group -NR4bR4c; R5 and R6 represent C1-C8 alkyl, C1-C8 haloalkyl, C3-C8 cycloalkyl, benzyl or phenyl or together with the nitrogen atom to which they are bound represent a 3- to 8-membered heterocycle; to Lewis acid adducts of compounds of formula (II.b); to the use of compounds of formula (II.a) or (II.b) and of the Lewis acid adducts thereof for producing compounds of formula (I) or (VI); and to a method for converting said compounds to the corresponding 3-difluoromethylpyrazole-4-yl carboxylic acids.
Abstract translation:本发明涉及一种用于制备式-3-二氟甲基吡唑(I)化合物其中R1是H,卤素,硝基,C1-C8烷基,C1-C8卤代烷基,C3-C8环烷基,苯基,萘基,杂芳基, 氰基,-C(= O)-OR1a,-C(= O)-NR1bR1c,-C(= O)-SR1d或-C(= S)-SR1e基; R2是H,C1-C4烷基,苄基或苯基; R 3为H,卤素,C1-C8烷氧基,C1-C8卤代烷氧基,C3-C8环烷氧基,C2-C8链烯氧基,C1-C8烷硫基,C1-C8卤代烷硫基,C3-C8-环烷硫基或C 2 -C C8-烯硫基;式(二.a)或(二.b)的化合物,其中R 1和R 3具有以上给出的含义之一; R 4是卤素,-OR4a,-SR4a,-O-SO2-R4A或一组-NR4bR4c基; R5和R6是C1-C8烷基,C1-C8卤代烷基,C3-C8环烷基,苄基或苯基或一起与氮原子到它们所键合的,代表3-至8-元杂环; 式(二.b)化合物的路易斯酸加合物;使用(二.a)或(二.b)和路易斯酸加合物,式I化合物的对式(I)或(VI)的化合物的制备方法; 并且这些化合物转变成相应的3-二氟甲基吡唑-4-基甲磺酸的方法。