US 2019/0161451 A1 · HERBICIDAL PYRIMIDINE COMPOUNDS

Abstract

The present invention relates to the pyrimidine compounds of formula (I), or their agriculturally acceptable salts or derivatives as herbicides, wherein the variables are defined according to the description, use of pyrimidine compounds of formula (I) as herbicides, 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 pyrimidine compound of the formula (I) to act on plants, their seed and/or their habitat.

Claims19

Dependent claims

1-15. (canceled)

A pyrimidine compound of formula (I)

wherein
the dotted line (------) is single bond or double bond;
R1 is C1-C6-alkyl, C1-C6-haloalkyl, HO—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-alkynyloxy, C3-C6-haloalkynyloxy, 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, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
wherein the cyclic groups of R1 are unsubstituted or substituted by Ra;
R2 is 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, C3-C6-alkenyloxy, C3-C6-alkenyloxy-C1-C6-alkoxy, C3-C6-haloalkenyloxy-C1-C6-haloalkoxy, C3-C6-alkenyloxy-C1-C6-haloalkoxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, C3-C6-alkynyloxy-C1-C6-alkoxy, C3-C6-haloalkynyloxy-C1-C6-haloalkoxy, C3-C6-alkynyloxy-C1-C6-haloalkoxy, C3-C6-alkynyloxy-C3-C6-alkenyloxy, C3-C6-haloalkynyloxy-C3-C6-alkenyloxy, C3-C6-alkynyloxy-C3-C6-haloalkenyloxy, C3-C6-haloalkynyloxy-C3-C6-haloalkenyloxy, C3-C6-alkynyloxy-C3-C6-alkynyloxy, C3-C6-haloalkynyloxy-C3-C6-alkynyloxy, C3-C6-alkynyloxy-C3-C6-haloalkynyloxy, C3-C6-haloalkynyloxy-C3-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-halo-cycloalkyl)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, (diphenyl)C═N—O, (C1-C6-alkyl)(phenyl)C═N—O, (di(C1-C6-alkyl))C═N—O, (C1-C6-alkyl)3-silyl-C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkoxy-C1-C6-alkylthio, C1-C6-haloalkoxy-C1-C6-alkylthio, C1-C6-alkoxy-C1-C6-haloalkylthio, C1-C6-halo-alkoxy-C1-C6-haloalkylthio, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkylthio, C1-C6-cyanoalkylthio, C3-C6-alkenylthio, C2-C6-haloalkenylthio, C3-C6-alkenyloxy-C1-C6-alkylthio, C3-C6-haloalkenyloxy-C1-C6-alkylthio, C3-C6-alkenyloxy-C1-C6-haloalkylthio, C3-C6-haloalkenyloxy-C1-C6-haloalkylthio, C3-C6-alkynylthio, C2-C6-haloalkynylthio, C3-C6-alkynyloxy-C1-C6-alkylthio, C3-C6-haloalkynyloxy-C1-C6-haloalkylthio, C3-C6-alkynyloxy-C1-C6-haloalkylthio, C3-C6-alkynyloxy-C3-C6-alkenylthio, C3-C6-haloalkynyloxy-C3-C6-alkenylthio, C3-C6-alkynyloxy-C2-C6-haloalkenylthio, C3-C6-haloalkynyloxy-C2-C6-haloalkenylthio, C3-C6-alkynyloxy-C3-C6-alkynylthio, C3-C6-haloalkynyloxy-C3-C6-alkynylthio, C3-C6-alkynyloxy-C2-C6-haloalkynylthio, C3-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)-aminocarbonyl-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, [(C1-C6-alkyl)carbonyl]amino, [(C1-C6-alkyl)carbonyl](C1-C6-alkyl)amino, [(C1-C6-haloalkyl)carbonyl]amino, [(C1-C6-haloalkyl)carbonyl](C1-C6-alkyl)amino, C3-C6-cycloalkylcarbonylamino, [(C3-C6-cycloalkyl)carbonyl](C1-C6-alkyl)amino, phenylcarbonylamino, (phenylcarbonyl)(C1-C6-alkyl)amino, heterocyclylcarbonylamino, (heterocyclylcarbonyl)(C1-C6-alkyl)amino, heteroarylcarbonylamino, (heteroarylcarbonyl)(C1-C6-alkyl)amino, [(C1-C6-alkyl)carbonyl](C1-C6-alkoxy)amino, [(C1-C6-haloalkyl)carbonyl](C1-C6-alkoxy)amino, [(C3-C6-cycloalkyl)carbonyl](C1-C6-alkyloxy)amino, (phenylcarbonyl)(C1-C6-alkoxy)amino, (heterocyclylcarbonyl)(C1-C6-alkoxy)amino, (heteroarylcarbonyl)(C1-C6-alkoxy)amino, [(C1-C6-alkyl)carbonyl](C2-C6-alkenyl)amino, [(C1-C6-haloalkyl)carbonyl](C2-C6-alkenyl)amino, [(C3-C6-cycloalkyl)carbonyl](C2-C6-alkenyl)amino, (phenylcarbonyl)(C2-C6-alkenyl)amino, (heterocyclylcarbonyl)(C2-C6-alkenyl)amino, (heteroarylcarbonyl)(C2-C6-alkenyl)amino, [(C1-C6-alkyl)carbonyl](C3-C6-alkynyl)amino, [(C1-C6-haloalkyl)carbonyl](C3-C6-alkynyl)amino, [(C3-C6-cycloalkyl)carbonyl](C3-C6-alkynyl)amino, (phenylcarbonyl)(C3-C6-alkynyl)amino, (heterocyclylcarbonyl)(C3-C6-alkynyl)amino, (heteroarylcarbonyl)(C3-C6-alkynyl)amino, [(C2-C6-alkenyl)carbonyl]amino, [(C2-C6-alkenyl)carbonyl](C1-C6-alkyl)amino, [(C2-C6-alkenyl)carbonyl](C1-C6-alkoxy)amino, [(C3-C6-alkynyl)carbonyl]amino, [(C3-C6-alkynyl)carbonyl](C1-C6-alkyl)amino, [(C3-C6-alkynyl)carbonyl](C1-C6-alkoxy)amino, [di(C1-C6-alkyl)amino]carbonylamino, [di(C1-C6-alkyl)aminocarbonyl](C1-C6-alkyl)amino, [di(C1-C6-alkyl)aminocarbonyl](C1-C6-alkoxy)amino, (heteroaryl)oxy, heteroaryl-C1-C6-alkoxy, (heterocyclyl)oxy, or heterocyclyl-C1-C6-alkoxy;
wherein the cyclic groups of R2 are unsubstituted or substituted by Ra;
Z is a 9 or 10 membered bicyclic ring comprising A;
A is C*, CR3, NR3A N, O, or S;
C* is a bridge carbon of the bicyclic ring Z;
R3 is halogen, CN, CHO, NO2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, 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 cyclic groups of R3 are unsubstituted or substituted by substituents Ra;
R3A is H, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, 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 cyclic groups of R3A are unsubstituted or substituted by Ra;
R4 is halogen, CN, CHO, NO2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, 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 cyclic groups of R4 are unsubstituted or substituted by Ra;
Ra is halogen, CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, or C1-C6-haloalkoxy;
m is 0, 1, 2, or 3;
provided that if ring Z is unsubstituted naphthalene, m is 1, 2, or 3;
or an agriculturally acceptable salt or derivative of the compound of formula (I) having an acidic functionality.

16 more elements

Dependencies are inferred from the claim text.

Facts

Application

16/320,822Filed 10 Jul 2017

Priority

EP 16180949.625 Jul 2016

Published

30 May 2019

Term ends

Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07D 239/36
One oxygen atom: as doubly bound oxygen atom or as unsubstituted hydroxy radical
A01N 43/54
Having rings with two nitrogen atoms as the only ring hetero atoms: 1,3-Diazines; Hydrogenated 1,3-diazines
C07D 239/28
Having three or more double bonds between ring members or between ring members and non-ring members: with hetero atoms or with carbon atoms having…
C07D 403/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond

Herbicidal pyrimidine compounds

Life of this patent

Herbicidal pyrimidine compounds

Life of this patent

Abstract

Claims19