US 10,420,341 B2 · Herbicidal phenylpyrimidines

Abstract

The present invention relates to the use of phenylpyrimidines of formula (I) or their agriculturally acceptable salts or derivatives as herbicides, wherein the variables are defined according to the description, specific phenylpyrimidines of formula (I), processes and intermediates for preparing the phenylpyrimidines of the formula (I), compositions comprising them and their use as herbicides, i.e. for controlling harmful plants, and also a method for controlling unwanted vegetation which comprises allowing a herbicidal effective amount of at least one phenylpyrimidine of the formula (I) to act on plants, their seed and/or their habitat.

A method for controlling undesired vegetation or harmful plants comprising allowing a herbicidal active amount of at least one compound of formula (I)

or agriculturally acceptable salt or derivative, wherein in formula (I) the variables have the following meanings:
R1 C1-C6-alkyl, C1-C6-haloalkyl, hydroxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkinyloxy, C3-C6-haloalkinyloxy, C1-C6-haloalkoxy, C3-C6-cycloalkoxy, C3-C6-halocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6-halocycloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, (C1-C6-alkyl)amino, di(C1-C6-alkyl)amino, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkyl, C3-C6-halocycloalkenyl, [1-(C1-C6-alkyl)]-C3-C6-cycloalkyl, [1-(C2-C6-alkenyl)]-C3-C6-cycloalkyl, [1-(C2-C6-alkynyl)]-C3-C6-cycloalkyl, [1-(C1-C6-haloalkyl)]-C3-C6-cycloalkyl, [1-(C2-C6-haloalkenyl)]-C3-C6-cycloalkyl, [1-(C3-C6-haloalkynyl)]-C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C3-C6-cycloalkyl-C1-C6-haloalkyl, C3-C6-cycloalkyl-C1-C6-alkoxy, C3-C6-cycloalkyl-C1-C6-haloalkoxy, 5 or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl,
wherein the cycloalkyl, heteroaryl and heterocyclyl substituents independently of one another are unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
R2 H, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-haloalkylcarbonyl-C1-C6-alkyl, C1-C6-haloalkoxycarbonyl-C1-C6-alkyl, C1-C6-alkylcarbonyl-C1-C6-haloalkyl, C1-C6-alkoxycarbonyl-C1-C6-haloalkyl, C1-C6-haloalkylcarbonyl-C1-C6-haloalkyl, C1-C6-haloalkoxycarbonyl-C1-C6-haloalkyl,
OH, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-haloalkoxy-C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-haloalkoxy, C1-C6-haloalkoxy-C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-cyanoalkoxy, C1-C6-hydroxyalkoxy, C2-C6-alkenyloxy, C2-C6-alkenyloxy-C1-C6-alkoxy, C2-C6-haloalkenyloxy-C1-C6-haloalkoxy, C2-C6-alkenyloxy-C1-C6-haloalkoxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C2-C6-alkynyloxy-C1-C6-alkoxy, C2-C6-haloalkynyloxy-C1-C6-haloalkoxy, C2-C6-alkynyloxy-C1-C6-haloalkoxy, C2-C6-alkynyloxy-C2-C6-alkenyloxy, C2-C6-haloalkynyloxy-C2-C6-alkenyloxy, C2-C6-alkynyloxy-C2-C6-haloalkenyloxy, C2-C6-haloalkynyloxy-C2-C6-haloalkenyloxy, C2-C6-alkynyloxy-C2-C6-alkynyloxy, C2-C6-haloalkynyloxy-C2-C6-alkynyloxy, C2-C6-alkynyloxy-C2-C6-haloalkynyloxy, C2-C6-haloalkynyloxy-C2-C6-haloalkynyloxy, (C1-C6-alkyl)carbonyl-C1-C6-alkoxy, (C1-C6-haloalkyl)carbonyl-C1-C6-haloalkoxy, (C1-C6-haloalkyl)carbonyl-C1-C6-alkoxy, (C1-C6-alkyl)carbonyl-C1-C6-haloalkoxy, (C1-C6-alkoxy)carbonyl-C1-C6-alkoxy, (C1-C6-haloalkoxy)carbonyl-C1-C6-alkoxy, (C1-C6-alkoxy)carbonyl-C1-C6-haloalkoxy, (C1-C6-haloalkoxy)-carbonyl-C1-C6-haloalkoxy, (C1-C6-alkoxy-C1-C6-alkyl)carbonyl-C1-C6-alkoxy, (C1-C6-haloalkoxy-C1-C6-alkyl)carbonyl-C1-C6-alkoxy, (C1-C6-alkoxy-C1-C6-haloalkyl)carbonyl-C1-C6-alkoxy, (C1-C6-alkoxy-C1-C6-alkyl)carbonyl-C1-C6-haloalkoxy, (C1-C6-haloalkoxy-C1-C6-haloalkyl)carbonyl-C1-C6-alkoxy, (C1-C6-haloalkoxy-C1-C6-alkyl)carbonyl-C1-C6-haloalkoxy, (C1-C6-alkoxy-C1-C6-haloalkyl)carbonyl-C1-C6-haloalkoxy, (C1-C6-haloalkoxy-C1-C6-haloalkyl)carbonyl-C1-C6-haloalkoxy, (C1-C6-alkylthio)carbonyl-C1-C6-alkoxy, (C1-C6-haloalkylthio)-carbonyl-C1-C6-alkoxy, (C1-C6-alkylthio)carbonyl-C1-C6-haloalkoxy, (C1-C6-haloalkylthio)carbonyl-C1-C6-haloalkoxy, (C1-C6-alkylthio-C1-C6-alkyl)carbonyl-C1-C6-alkoxy, (C1-C6-haloalkylthio-C1-C6-alkyl)carbonyl-C1-C6-alkoxy, (C1-C6-alkylthio-C1-C6-haloalkyl)carbonyl-C1-C6-alkoxy, (C1-C6-alkylthio-C1-C6-alkyl)carbonyl-C1-C6-haloalkoxy, (C1-C6-haloalkylthio-C1-C6-haloalkyl)carbonyl-C1-C6-alkoxy, (C1-C6-haloalkylthio-C1-C6-alkyl)carbonyl-C1-C6-haloalkoxy, (C1-C6-alkylthio-C1-C6-haloalkyl)carbonyl-C1-C6-haloalkoxy, (C1-C6-haloalkylthio-C1-C6-haloalkyl)carbonyl-C1-C6-haloalkoxy, C3-C6-cycloalkoxy, C3-C6-halocycloalkoxy, (C3-C6-cycloalkyl)C1-C6-alkoxy, (C3-C6-halocycloalkyl)C1-C6-alkoxy, (C3-C6-cycloalkyl)C1-C6-haloalkoxy, aminocarbonyl-C1-C6-alkoxy, (C3-C6-halocycloalkyl)-C1-C6-haloalkoxy, aminocarbonyl-C1-C6-haloalkoxy, N—(C1-C6-alkyl)-aminocarbonyl-C1-C6-alkoxy, N—(C1-C6-alkyl)-aminocarbonyl-C1-C6-haloalkoxy, N,N-di(C1-C6-alkyl)-aminocarbonyl-C1-C6-alkoxy, N,N-di(C1-C6-alkyl)-aminocarbonyl-C1-C6-haloalkoxy,
O—N═C(di(phenyl), O—N═C(phenyl)(C1-C6-alkyl), O—N═C[di(C1-C6-alkyl)], (C1-C6-alkyl)3-silyl-C1-C6-alkoxy,
C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkoxy-C1-C6-alkylthio, C1-C6-halo-alkoxy-C1-C6-alkylthio, C1-C6-alkoxy-C1-C6-haloalkylthio, C1-C6-haloalkoxy-C1-C6-haloalkylthio, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkylthio, C1-C6-cyanoalkylthio, C2-C6-alkenylthio, C2-C6-haloalkenylthio, C2-C6-alkenyloxy-C1-C6-alkylthio, C2-C6-haloalkenyloxy-C1-C6-alkylthio, C2-C6-alkenyloxy-C1-C6-haloalkylthio, C2-C6-haloalkenyloxy-C1-C6-haloalkylthio, C2-C6-alkynylthio, C2-C6-haloalkynylthio, C2-C6-alkynyloxy-C1-C6-alkylthio, C2-C6-haloalkynyloxy-C1-C6-haloalkylthio, C2-C6-alkynyloxy-C1-C6-haloalkylthio, C2-C6-alkynyloxy-C2-C6-alkenylthio, C2-C6-haloalkynyloxy-C2-C6-alkenylthio, C2-C6-alkynyloxy-C2-C6-haloalkenylthio, C2-C6-haloalkynyloxy-C2-C6-haloalkenylthio, C2-C6-alkynyloxy-C2-C6-alkynylthio, C2-C6-haloalkynyloxy-C2-C6-alkynylthio, C2-C6-alkynyloxy-C2-C6-haloalkynylthio, C2-C6-haloalkynyloxy-C2-C6-haloalkynylthio, (C1-C6-alkyl)carbonyl-C1-C6-alkylthio, (C1-C6-haloalkyl)carbonyl-C1-C6-alkylthio, (C1-C6-alkyl)carbonyl-C1-C6-haloalkylthio, (C1-C6-haloalkyl)carbonyl-C1-C6-haloalkylthio, (C1-C6-alkoxy)carbonyl-C1-C6-alkylthio, (C1-C6-haloalkoxy)carbonyl-C1-C6-alkylthio, (C1-C6-alkoxy)carbonyl-C1-C6-haloalkylthio, (C1-C6-haloalkoxy)carbonyl-C1-C6-haloalkylthio, (C1-C6-alkoxy-C1-C6-alkyl)carbonyl-C1-C6-alkylthio, (C1-C6-haloalkoxy-C1-C6-alkyl)carbonyl-C1-C6-alkylthio, (C1-C6-alkoxy-C1-C6-haloalkyl)carbonyl-C1-C6-alkylthio, (C1-C6-alkoxy-C1-C6-alkyl)carbonyl-C1-C6-haloalkylthio, (C1-C6-haloalkoxy-C1-C6-haloalkyl)carbonyl-C1-C6-alkylthio, (C1-C6-haloalkoxy-C1-C6-alkyl)carbonyl-C1-C6-haloalkylthio, (C1-C6-alkoxy-C1-C6-haloalkyl)carbonyl-C1-C6-haloalkylthio, (C1-C6-haloalkoxy-C1-C6-haloalkyl)carbonyl-C1-C6-haloalkylthio, (C1-C6-alkylthio)carbonyl-C1-C6-alkylthio, (C1-C6-haloalkylthio)carbonyl-C1-C6-alkylthio, (C1-C6-alkylthio)carbonyl-C1-C6-haloalkylthio, (C1-C6-haloalkylthio)carbonyl-C1-C6-haloalkylthio, (C1-C6-alkylthio-C1-C6-alkyl)carbonyl-C1-C6-alkylthio, (C1-C6-haloalkylthio-C1-C6-alkyl)carbonyl-C1-C6-alkylthio, (C1-C6-alkylthio-C1-C6-haloalkyl)carbonyl-C1-C6-alkylthio, (C1-C6-alkylthio-C1-C6-alkyl)carbonyl-C1-C6-haloalkylthio, (C1-C6-haloalkylthio-C1-C6-haloalkyl)carbonyl-C1-C6-alkylthio, (C1-C6-haloalkylthio-C1-C6-alkyl)carbonyl-C1-C6-haloalkylthio, (C1-C6-alkylthio-C1-C6-haloalkyl)carbonyl-C1-C6-haloalkylthio, (C1-C6-haloalkylthio-C1-C6-haloalkyl)carbonyl-C1-C6-haloalkylthio, C3-C6-cycloalkylthio, C3-C6-halocycloalkylthio, (C3-C6-cycloalkyl)C1-C6-alkylthio, (C3-C6-cycloalkyl)C1-C6-haloalkylthio, (C3-C6-halocycloalkyl)C1-C6-alkylthio, (C3-C6-halocycloalkyl)C1-C6-haloalkylthio, aminocarbonyl-C1-C6-alkylthio, aminocarbonyl-C1-C6-haloalkylthio, N—(C1-C6-alkyl)-aminocarbonyl-C1-C6-alkylthio, N—(C1-C6-haloalkyl)-amino-carbonyl-C1-C6-alkylthio, N—(C1-C6-alkyl)-aminocarbonyl-C1-C6-haloalkylthio, N—(C1-C6-haloalkyl)-aminocarbonyl-C1-C6-haloalkylthio, N,N-di(C1-C6-alkyl)-aminocarbonyl-C1-C6-alkylthio, N,N-di(C1-C6-haloalkyl)-aminocarbonyl-C1-C6-alkylthio, N,N-di(C1-C6-alkyl)-aminocarbonyl-C1-C6-haloalkylthio, N,N-di(C1-C6-haloalkyl)-aminocarbonyl-C1-C6-haloalkylthio,
NH2, (C1-C6-alkyl)amino, hydroxyamino, (C1-C6-alkoxy)amino, (C3-C6-cycloalkoxy)amino, (C1-C6-alkyl)sulfinylamino, (C1-C6-alkyl)sulfonylamino, (amino)sulfinylamino, [(C1-C6-alkyl)amino]sulfinylamino, (amino)sulfonylamino, [(C1-C6-alkyl)amino]sulfonylamino, [di(C1-C6-alkyl)amino]sulfonylamino, di(C1-C6-alkyl)amino, (hydroxy)(C1-C6-alkyl)amino, (hydroxy)(C1-C6-cycloalkyl)amino, (C1-C6-alkoxy)(C1-C6-alkyl)amino, (C1-C6-alkoxy)(C3-C6-cycloalkyl)amino, (C3-C6-cycloalkoxy)(C1-C6-alkyl)amino, (C3-C6-cycloalkoxy)(C3-C6-cycloalkyl)amino, [(C1-C6-alkyl)sulfinyl](C1-C6-alkyl)amino, [(C1-C6-alkyl)sulfonyl](C1-C6-alkyl)amino, [di(C1-C6-alkyl)amino]sulfinylamino, [di(C1-C6-alkyl)amino]sulfonylamino, phenyloxy, phenyl-C1-C6-alkoxy, phenylthio, phenyl-C1-C6-alkylthio, phenylamino, (C1-C6-alkyl)(phenyl)amino, (heteroaryl)oxy, heteroaryl-C1-C6-alkoxy, (heterocyclyl)oxy, heterocyclyl-C1-C6-alkoxy,
wherein the phenyl, heteroaryl and heterocyclyl substituents independently from one another are unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
R3 halogen, CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkinyl, C2-C6-haloalkinyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkinyloxy, C2-C6-haloalkinyloxy, C1-C6-alkoxy-C1-C6-alkoxy, hydroxycarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio, NH2, (C1-C6-alkyl)amino, di(C1-C6-alkyl)amino, (C1-C6-alkyl)sulfinyl, (C1-C6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)oxy or phenyl;
wherein the cycloalkyl, (cycloalkyl)oxy, or phenyl substituents independently from one another are unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
and
R4, R5, R6 and R7 independently of one another
H, halogen, CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkinyl, C2-C6-haloalkinyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkinyloxy, C2-C6-haloalkinyloxy, C1-C6-alkoxy-C1-C6-alkoxy, hydroxycarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio, NH2, (C1-C6-alkyl)amino, di(C1-C6-alkyl)amino, (C1-C6-alkyl)sulfinyl, (C1-C6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)oxy or phenyl;
wherein the cycloalkyl, (cycloalkyl)oxy, or phenyl substituents independently from one another are unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
to act on undesired vegetation, harmful plants, their environment or on crop seed.

13 more elements

Herbicidal phenylpyrimidines

Life of this patent

Herbicidal phenylpyrimidines

Life of this patent

Abstract

Claims7