US 9,101,133 B2 · Phenyl-substituted bicyclooctane-1,3-dione-derivatives

Abstract

The invention relates to novel compounds of the formula (I) in which R1, R2, R3, R4, R5, Y, Q and G have the meanings given above, to a plurality of processes and intermediates for their preparation and to their use as herbicides and/or pesticides. Moreover, the invention relates to selective herbicidal compositions comprising, firstly, the phenyl-substituted bicyclooctane-1,3-dione derivates and, secondly, a crop plant compatibility-improving compound. The present invention furthermore relates to increasing the activity of crop protection compositions comprising in particular phenyl-substituted bicyclooctane-1,3-dione derivates by adding ammonium salts or phosphonium salts and, if appropriate, penetrants, to the corresponding compositions, to processes for their preparation and to their use in crop protection as pesticides and/or for preventing unwanted plant growth.

A compound of formula (I)

wherein the following isomeric forms can be included:
in which
Q represents a bond, a C1-C3-alkylene, a C2-C3-alkenylene or a C2-C3-alkynylene chain,
Y represents the groups —OR6, —S(O)pR6, —CO2R7, —CH═CH2, cyano, —SCN, —CONR8R9, —SO2NR8R9, —CR10═O, —NR11R12, —CR10═N—OR13, —CR10═N—R14, CR10═N—NR15R16, —CR10(OR17OR18), —CR10(SR17OR18), —CR10(SR17SR18), —CR10(NHR17NHR18), —CR10(NHR17OR18), —CR10(NHR17SR18), —CH(CN)2, —CH(OH)R6, halogen, —O(C=M)R10, —S(C=M)R10, —O(C=M)NR11R12, —S(C=M)NR11R12, —NH(C=M)NR11R12, —O(C=M)OR7, —S(C=M)OR7, —NH(C=M)OR7 or represents the group W,
or Q, Y and R5 together form one of the groups CHCN═, CH(CO2C1-C6-alkyl)═,
W represents a 3- to 7-membered saturated or partially saturated heterocycle which contains at least one heteroatom optionally oxygen, sulphur or nitrogen and may additionally be mono- or polysubstituted by identical or different substituents, G represents hydrogen, methyl, ethyl or benzyl (a) or represents one of the groups
E represents a metal ion equivalent, a tertiary sulphonium ion or an ammonium ion,
L represents oxygen or sulphur,
M represents oxygen or sulphur,
R1 represents hydrogen, halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, halo-C2-C6-alkynyl, C1-C6-alkoxy, halo-C1-C6-alkoxy, C3-C6-cycloalkoxy, halo-C3-C6-cycloalkoxy, C2-C6-alkynyloxy, halo-C2-C6-alkynyloxy, C2-C6-alkenyloxy, halo-C2-C6-alkenyloxy, C1-C3-alkylthio, C1-C3-alkylsulphinyl, C1-C3-alkylsulphonyl, halo-C1-C3-alkylthio, halo-C1-C3-alkylsulphinyl or halo-C1-C3-alkylsulphonyl,
R2 and R3 independently of one another are identical or different and represent hydrogen, halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, halo-C2-C6-alkynyl, C1-C6-alkoxy, halo-C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, halo-C3-C6-cycloalkoxy, C2-C6-alkynyloxy, halo-C2-C6-alkynyloxy, C2-C6-alkenyloxy, halo-C2-C6-alkenyloxy, C1-C3-alkylthio, C1-C3-alkylsulphinyl, C1-C3-alkylsulphonyl, halo-C1-C3-alkylthio, halo-C1-C3-alkylsulphinyl, halo-C1-C3-alkylsulphonyl, phenyl or phenyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, C1-C4-alkyl, halo-C1-C4-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, C1-C6-alkoxy, halo-C1-C6-alkoxy, nitro and cyano,
R4 represents hydrogen, halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, C1-C6-alkoxy, halo-C1-C6-alkoxy, C3-C6-cycloalkoxy, or halo-C3-C6-cycloalkoxy,
R5 represents hydrogen or C1-C4-alkyl,
R6 represents hydrogen, C1-C6-alkyl, halo-C1-C6-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, halo-C2-C6-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, halo-C1-C4-alkoxy-C1-C4-alkyl, C3-C6-cycloalkoxy-C1-C4-alkyl, halo-C3-C4-cycloalkoxy-C1-C4-alkyl, represents benzyl, phenyl, heteroaryl, —CH2-heteroaryl, —CH2CH2-heteroaryl, pyranyl, tetrahydrofuranyl, C1-C4-alkanoyl, halo-C1-C4-alkanoyl, benzoyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, halo-C2-C6-alkynyl, C1-C4-alkoxyalkyl, halo-C1-C4-alkoxy-C1-C6-alkyl, C3-C6-cycloalkoxy-C1-C6-alkyl and halo-C3-C6-cycloalkoxy-C1-C6-alkyl, or represents benzoyl, which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C3-C6-cycloalkyl and halo-C3-C6-cycloalkyl,
R7 represents hydrogen, represents in each case optionally substituted C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl or represents a cation E,
R8 and R9 independently of one another are identical or different and represent hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, represent phenyl or benzyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano and C1-C3-alkyl or
R8 and R9 together with the adjacent nitrogen atom form a morpholino, piperidino or pyrrolidino group,
R10 represents hydrogen, C1-C6-alkyl, halo-C1-C4-alkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, represents phenyl or benzyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, C1-C6-alkyl and halo-C1-C6-alkyl,
R11 and R12 independently of one another are identical or different and represent hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, represent phenyl or benzyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano and C1-C3-alkyl or
R11 and R12 together with the adjacent nitrogen atom form a morpholino, piperidino or pyrrolidino group,
R13 represents hydrogen or represents C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C3-alkyl, each of which is optionally interrupted at least once by oxygen or sulphur and is optionally mono- or polysubstituted by halogen, represents benzyl or —CH2-heterocyclyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano and C1-C3-alkyl,
R14 represents hydrogen, C1-C6-alkyl, halo-C1-C6-alkyl, C2-C6-alkenyl, halo-C2-C6-alkenyl, C2-C6-alkynyl, halo-C2-C6-alkynyl, phenyl, benzyl or represents phenyl or benzyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of halogen, C1-C3-alkyl, halo-C1-C3-alkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, nitro and cyano,
R15 and R16 independently of one another are identical or different and represent hydrogen, C1-C5-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, represent phenyl or benzyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano and C1-C3-alkyl or
R15 and R16 together with the adjacent nitrogen atom form a morpholino, piperidino or pyrrolidino group,
R17 represents hydrogen, represents C1-C6-alkyl, benzyl or halo-C1-C6-alkyl, each of which is optionally interrupted at least once by identical or different radicals from the group consisting of oxygen and sulphur,
R18 represents hydrogen, represents C1-C6-alkyl, benzyl or halo-C1-C6-alkyl, each of which is optionally interrupted at least once by identical or different radicals from the group consisting of oxygen and sulphur,
R19 represents optionally halogen-substituted C1-C6-alkyl, C2-C6-alkenyl, C1-C4-alkoxy-C1-C4alkyl, C1-C3-alkylthio-C1-C4-alkyl, poly-C1-C4-alkoxy-C1-C4-alkyl or represents C3-C6-cycloalkyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, C1-C4-alkyl and C1-C4-alkoxy and may optionally be interrupted in the ring by oxygen or sulphur, represents phenyl, phenyl-C1-C4-alkyl, hetaryl, phenoxy-C1-C4-alkyl or hetaryloxy-C1-C4-alkyl, each of which is optionally substituted by halogen or C1-C4-alkyl,
R20 represents C1-C6-alkyl, C2-C6-alkenyl, C1-C4-alkoxy-C1-C4-alkyl, poly-C1-C4-alkoxy-C1-C4-alkyl, each of which is optionally mono- or polysubstituted by identical or different halogen, or represents C3-C6-cycloalkyl which may optionally be interrupted in the ring by oxygen or sulphur, or represents benzyl,
R21, R22 and R23 independently of one another are identical or different and represent C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylamino, C1-C6-dialkylamino, C1-C3-alkylthio, C2-C4-alkenylthio, C3-C6-cycloalkylthio, each of which is optionally mono- or polysubstituted by identical or different halogen, or represent phenyl, benzyl, phenoxy or phenylthio,
R24 and R25 independently of one another are identical or different and represent hydrogen, represent C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C4-alkyl, each of which is optionally mono- or polysubstituted by identical or different halogen, represent phenyl or benzyl, optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and C1-C4-alkyl or
R24 and R25 together with the adjacent nitrogen atom form a morpholino, piperidino or pyrrolidino group,
P represents the number 0, 1 or 2,
or if
Q, Y and R5 together represent the group CH2═, then
G represents methyl, ethyl or benzyl (a).

32 more elements

Phenyl-substituted bicyclooctane-1,3-dione-derivatives

Life of this patent

Phenyl-substituted bicyclooctane-1,3-dione-derivatives

Life of this patent

Abstract

Claims14