Substituted N-[pyrimidin-2-ylmethyl]carboxamides and their use as herbicides and plant growth regulators
What is described are N-[pyrimidin- 2 -ylmethyl]carboxamides of the formula (I) and their use as herbicides. In this formula (I), X 1 and X 2 are hydrogen or methyl, R 1 to R 4 are various radicals and A is an aromatic or heteroaromatic ring.
1 . A compound of the formula (I), its N-oxide and/or its salt,
in which the radicals and indices are as defined below:
R 1 and R 2 independently of one another are hydrogen, halogen, cyano, amino, isocyanato, hydroxyl, nitro, COOR 5 , COR 5 , CH 2 OH, CH 2 SH, CH 2 NH 2 , (C 1 -C 4 )-alkyl, halo-(C 1 -C 4 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkoxy, halo-(C 1 -C 4 )-alkoxy, (C 1 -C 2 )-alkoxy-(C 1 -C 2 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, (C 3 -C 4 )-alkenyloxy, (C 3 -C 4 )-alkynyloxy, (C 1 -C 2 )-alkylthio-(C 1 -C 2 )-alkyl, S(O) n R 6 (C 1 -C 2 )-alkylsulfonyl-(C 1 -C 2 )-alkyl, (C 1 -C 4 )-alkyl-NH, (C 1 -C 3 )-alkyl-CO—NH, (C 1 -C 4 )-alkyl-SO 2 NH, di-(C 1 -C 4 )-alkylamino,
or R 1 and R 2 together form the group (CH 2 ) 3 ;
R 3 is hydrogen, (C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, benzyl, COOR 5 , COR 4 or S(O) n R 6 ;
R 4 is hydrogen, (C 1 -C 8 )-alkyl, (C 2 -C 8 )-alkenyl, (C 2 -C 8 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl which is substituted by one or two methyl groups, (C 1 -C 2 )-alkoxy-(C 1 -C 2 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 2 )-alkyl, halo-(C 1 -C 6 )-alkyl or halo-(C 3 -C 6 )-cycloalkyl;
R 5 is hydrogen or (C 1 -C 4 )-alkyl;
R 6 is hydrogen, (C 1 -C 4 )-alkyl or halo-(C 1 -C 4 )-alkyl;
A is a radical from the group comprising the substituents A1 to A8
R 8 is hydrogen, halogen, cyano, isocyanato, nitro, (C 1 -C 4 )-alkyl, halo-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, halo-(C 1 -C 4 )-alkoxy, halo-(C 1 -C 4 )-alkylthio, (C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, SF 5 , S(O) n R 6 , (C 2 -C 4 )-alkenyl or (C 2 -C 4 )-alkynyl;
R 9 is hydrogen, halogen, cyano, isocyanato, nitro, (C 1 -C 4 )-alkyl, halo-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, halo-(C 1 -C 4 )-alkoxy, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, (C 3 -C 6 )-cycloalkyl or S(O) n R 6 ;
R 10 is (C 1 -C 4 )-alkyl;
X 1 , X 2 independently of one another are hydrogen or (C 1 -C 4 )-alkyl;
n is 0, 1 or 2.
2 . The compound as claimed in claim 1 , in which
R 1 and R 2 independently of one another are hydrogen, halogen, cyano, hydroxyl, nitro, (C 1 -C 2 )-alkyl, halo-(C 1 -C 2 )-alkyl, (C 1 -C 2 )-alkoxy, halo-(C 1 -C 2 )-alkoxy, (C 1 -C 2 )-alkoxy-(C 1 -C 2 )-alkyl, (C 1 -C 2 )-alkylthio-(C 1 -C 2 )-alkyl, S(O) n —(C 1 -C 2 )-alkyl,
or R 1 and R 2 together form the group (CH 2 ) 3 ;
R 3 is hydrogen, (C 1 -C 2 )-alkyl, benzyl or COR 4 ;
R 4 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl which is substituted by a methyl group, (C 1 -C 2 )-alkoxy-(C 1 -C 2 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 2 )-alkyl, halo-(C 1 -C 4 )-alkyl or halo-(C 3 -C 6 )-cycloalkyl;
R 5 is hydrogen or (C 1 -C 4 )-alkyl;
R 6 is hydrogen, (C 1 -C 2 )-alkyl or halo-(C 1 -C 2 )-alkyl;
A is a radical from the group comprising the substituents A1 to A8;
R 8 is hydrogen, halogen, cyano, (C 1 -C 2 )-alkyl, halo-(C 1 -C 2 )-alkyl, (C 1 -C 2 )-alkoxy, halo-(C 1 -C 2 )-alkoxy, halo-(C 1 -C 2 )-alkylthio, (C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, S(O) n R 6 , (C 2 -C 4 )-alkenyl or (C 2 -C 4 )-alkynyl;
R 9 is hydrogen, halogen, cyano, nitro, (C 1 -C 2 )-alkyl, halo-(C 1 -C 2 )-alkyl, (C 1 -C 2 )-alkoxy, halo-(C 1 -C 2 )-alkoxy, (C 2 -C 2 )-alkenyl, (C 2 -C 4 )-alkynyl, (C 3 -C 6 )-cycloalkyl or S(O) n R 6 ;
R 10 is methyl or ethyl;
X 1 , X 2 independently of one another are hydrogen or methyl;
n is 0, 1 or 2.
3 . The compound as claimed in claim 1 , in which
R 1 and R 2 independently of one another are hydrogen, halogen, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy, ethoxymethyl, methoxymethyl, thiomethyl, methylsulfonyl,
or R 1 and R 2 together form the group (CH 2 ) 3 ;
R 3 is hydrogen, methyl, ethyl or COR 4 ;
R 4 is hydrogen, (C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, (C 3 -C 6 )-cycloalkyl, cyclopropyl which is substituted by a methyl group, (C 1 -C 2 )-alkoxy-(C 1 -C 2 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 2 )-alkyl, halo-(C 1 -C 4 )-alkyl or halo-(C 3 -C 6 )-cycloalkyl;
R 5 is hydrogen or (C 1 -C 4 )-alkyl;
R 6 is hydrogen, methyl or ethyl;
R 7 is hydrogen, (C 1 -C 4 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 2 )-alkyl, halo-(C 1 -C 4 )-alkyl or halo-(C 3 -C 6 )-cycloalkyl;
A is a radical from the group comprising the substituents A1 to A6;
R 8 is hydrogen, halogen, cyano, methyl, ethyl, halo-(C 1 -C 2 )-alkyl, (C 1 -C 2 )-alkoxy, halomethoxy, (C 3 -C 6 )-cycloalkyl or S(O) n R 6 ;
R 9 is hydrogen, halogen, cyano, nitro, methyl, ethyl, halo-(C 1 -C 2 )-alkyl, (C 1 -C 2 )-alkoxy, halomethoxy, (C 2 -C 2 )-alkenyl, (C 2 -C 4 )-alkynyl, (C 3 -C 6 )-cycloalkyl or S(O) n R;
R 10 is methyl or ethyl;
X 1 , X 2 are hydrogen;
n is 0 or 2.
4 . A herbicidal composition comprising a herbicidally effective amount of at least one compound of the formula (I) as claimed in claim 1 .
5 . The herbicidal composition as claimed in claim 4 as a mixture with formulating auxiliaries.
6 . A method of controlling unwanted plants, which comprises applying to the plants or to the locus of unwanted plant growth an effective amount of a compound of the formula (I) as claimed in claim 1 .
7 . (canceled)
8 . (canceled)
9 . (canceled)
10 . A method of controlling unwanted plants, which comprises applying to the plants or to the locus of unwanted plant growth an effective amount of a compound of the formula (I) as claimed in claim 4 .
11 . A method of controlling unwanted plants, which comprises applying to the plants or to the locus of unwanted plant growth an effective amount of a compound of the formula (I) as claimed in claim 5 .
12 . The method of claim 6 , wherein the unwanted plants are present in crops of useful plants.
13 . The method of claim 12 , wherein the useful plants are transgenic useful plants.
14 . The method of claim 10 , wherein the unwanted plants are present in crops of useful plants.
15 . The method of claim 14 , wherein the useful plants are transgenic useful plants.
16 . The method of claim 11 , wherein the unwanted plants are present in crops of useful plants.
17 . The method of claim 16 , wherein the useful plants are transgenic useful plants.