N-(1,2,5-oxadiazol-3-yl)-, N-(1,3,4-oxadiazol-2-yl)-, N-(tetrazol-5-yl)-, and N-(triazol-5-yl) aryl carboxylic acid amides and use thereof as herbicides
View Patent ↗N-(1,2,5-Oxadiazol-3-yl)-, N-(1,3,4-oxadiazol-2-yl)-, N-(tetrazol-5-yl)- or N-(triazol-5 -yl)arylcarboxamides of the general formula (I) are described as herbicides. In this formula (I), R, V, X, Y and Z are radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. Q is a tetrazolyl, triazolyl or oxadiazolyl radical. W is CY or N.
1. An N-(tetrazol-5-yl)- arylcarboxamide of formula (I) and/or a salt thereof
in which
R is methyl, ethyl, allyl, —CH2CO2Me, —CH2OEt, propargyl, or benzyl,
Y is hydrogen, SO2Me, OH, or chloro,
X and Z are independently methyl, chloro, CF3, SO2Me, or SO2Et,
W is CY,
V is hydrogen,
Q is a Q1, radical,
R 6 is (C 1 C 6 )-alkyl, halo-(C 1 C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 2 -C 6 )-alkynyl,
where these 6 aforementioned radicals are each substituted by s radicals from the group consisting of nitro, cyano, SiR 12 3 , PO(OR 12 ) 3 , S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, N(R 10 ) 2 , COR 10 , COOR 10 , OCOR 10 , OCO 2 R 10 , NR 10 COR 10 , NR 10 SO 2 R 11 , (C 3 -C 6 )-cycloalkyl, phenyl,-D-phenyl or D-benzyl, and where the 3 latter radicals are substituted by s radicals from the group of methyl, ethyl, methoxy, trifluoromethyl and halogen, or
R 6 is (C 3 C 7 )-cycloalkyl, or phenyl, each substituted by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy and (C 1 -C 6 )-alkoxy -(C 1 -C 4 )-alkyl,
R 10 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl or phenyl,
R 11 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl or phenyl,
R 12 is (C 1 -C 6 )-alkyl,
D is O, S, or NR 11 .
2. A herbicidal composition, comprising a herbicidally active content of at least one compound as claimed in claim 1 and a formulation assistant.
3. A method for controlling unwanted plants, which comprises applying an effective amount of at least one compound as claimed in claim 1 to a plant and/or a site of unwanted vegetation.
4. A compound as claimed in claim 1 , wherein
R is allyl, —CH2CO2Me, —CH2OEt, propargyl, or benzyl,
Y is hydogen, SO2Me, OH, or chloro, and
X and Z are independently methyl, chloro, CF3, SO2Me, or SO2Et.
5. A compound as claimed in claim 1 , wherein R is benzyl.
6. A compound as claimed in claim 1 , wherein X and Z are each independently chloro, CF3, SO2Me, or SO2Et.