N-(1,2,5-oxadiazol-3-yl)benzamides and their use as herbicides
View Patent ↗There are described N-(1,2,5-oxadiazol-3-yl)benzamides of the general formula (I) as herbicides. In this formula (I), X, Y, Z and R are radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen.
1. A compound of the formula (I) or a salt thereof
in which
R is hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkenyloxy, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-alkynyloxy, (C 2 -C 6 )-haloalkynyl, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl or
heteroaryl, heterocyclyl or phenyl, each of which is substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen,
X and Z independently of one another are in each case nitro, halogen, cyano, formyl, rhodano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-haloalkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halocycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-halocycloalkyl-(C 1 -C 6 )-alkyl, COR 1 , OR 1 , OCOR 1 , OSO 2 R 2 , S(O) n R 2 , SO 2 OR 1 , SO 2 N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-OCOR 1 , (C 1 -C 6 )-alkyl-OSO 2 R 2 , (C 1 -C 6 )-alkyl-COOR 1 , (C 1 -C 6 )-alkyl-SO 2 OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 , NR 1 R 2 , P(O)(OR 5 ) 2 , or
heteroaryl, heterocyclyl or phenyl, each of which is substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen,
Y is S(O) n R 2 , 4,5-dihydro-1,2-oxazol-3-yl, 5-cyanomethyl-4,5-dihydro-1,2-oxazol-3-yl or 5-methoxymethyl-4,5-dihydro-1,2-oxazol-3-yl,
R 1 is hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halocycloalkyl, (C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl or phenyl-(C 1 -C 6 )-alkyl, where the 12 last-mentioned radicals are substituted by s radicals selected from the group consisting of cyano, halogen, nitro, rhodano, OR 3 , S(O) n R 4 , N(R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , SCOR 3 , NR 3 COR 3 , CO 2 R 3 , COSR 3 , CON(R 3 ) 2 and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl,
R 2 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl or phenyl-(C 1 -C 6 )-alkyl, where the seven last-mentioned radicals are substituted by s radicals selected from the group consisting of cyano, halogen, nitro, thiocyanato, OR 3 , S(O) n R 4 , N(R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , SCOR 3 , NR 3 COR 3 , CO 2 R 3 , COSR 3 , CON(R 3 ) 2 and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl,
R 3 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl,
R 4 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl,
R 5 is methyl or ethyl,
n is 0, 1 or 2, and
s is 0, 1, 2 or 3.
2. The compound or salt as claimed in claim 1 , wherein
R is hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl,
a heterocycle selected from the group consisting of pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, benzisoxazol-2-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-triazol-3-yl, 1-ethylbenzimidazol-2-yl, 4-methylthiazol-2-yl, thiophen-2-yl, furan-2-yl, furan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, isoxazol-2-yl, isoxazol-3-yl, oxazol-2-yl, oxazol-3-yl, pyrrol-2-yl, pyrrol-3-yl, imidazol-2-yl, imidazol-5-yl, imidazol-4-yl, pyrazol-3-yl, pyrazol-5-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, 1,2,3-triazol-4-yl, 1,2,3-triazol-5-yl, 1,2,5-triazol-3-yl, 1,3,4-triazol-2-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,5-thiadiazol-3-yl, 2H-1,2,3,4-tetrazol-5-yl, 1H-1,2,3,4-tetrazol-1-yl, 1,2,3,4-oxatriazol-5-yl, 1,2,3,5-oxatriazol-4-yl, 1,2,3,4-thiatriazol-5-yl, 1,2,3,5-thiatriazol-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl and pyridazin-4-yl,
which heterocycle is substituted by s radicals selected from the group consisting of methyl, methoxy and halogen, or
phenyl which is substituted by s radicals selected from the group consisting of methyl, methoxy, trifluoromethyl and halogen,
X and Z independently of each other are in each case nitro, halogen, cyano, rhodano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-haloalkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halocycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-halocycloalkyl-(C 1 -C 6 )-alkyl, COR 1 , OR 1 , OCOR 1 , OSO 2 R 2 , S(O) n R 2 , SO 2 OR 1 , SO 2 N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-OCOR 1 , (C 1 -C 6 )-alkyl-OSO 2 R 2 , —C 6 )-alkyl-COOR 1 , (C 1 -C 6 )-alkyl-SO 2 OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , —C 6 )-alkyl-NR 1 COR 1 , —C 6 )-alkyl-NR 1 SO 2 R 2 , benzoxazol-2-yl, 1-ethylbenzimidazol-2-yl, piperidin-1-yl or 1,2,4-triazol-1-yl,
Y 4,5-dihydro-1,2-oxazol-3-yl, 5-cyanomethyl-4,5-dihydro-1,2-oxazol-3-yl or 5-methoxymethyl-4,5-dihydro-1,2-oxazol-3-yl,
R 1 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl or phenyl-(C 1 -C 6 )-alkyl, where the seven last-mentioned radicals are substituted by s radicals selected from the group consisting of cyano, halogen, nitro, thiocyanato, OR 3 , S(O) n R 4 , N(R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , SCOR 3 , NR 3 COR 3 , CO 2 R 3 , COSR 3 , CON(R 3 ) 2 and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl,
R 2 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl or phenyl-(C 1 -C 6 )-alkyl, where the seven last-mentioned radicals are substituted by s radicals selected from the group consisting of cyano, halogen, nitro, thiocyanato, OR 3 , S(O) n R 4 , N(R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , SCOR 3 , NR 3 COR 3 , CO 2 R 3 , COSR 3 , CON(R 3 ) 2 and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl,
R 3 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl,
R 4 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl,
n is 0, 1 or 2, and
s is 0, 1, 2 or 3.
3. The compound or salt as claimed in claim 1 , wherein
R is hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halogen-(C 1 -C 6 )-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl,
X and Z independently of one another are in each case nitro, halogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 6 )-cycloalkyl, OR 1 , S(O) n R 2 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 or 1,2,4-triazol-1-yl,
Y 4,5-dihydro-1,2-oxazol-3-yl, 5-cyanomethyl-4,5-dihydro-1,2-oxazol-3-yl or 5-methoxymethyl-4,5-dihydro-1,2-oxazol-3-yl,
R 1 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl or phenyl-(C 1 -C 6 )-alkyl, where the seven last-mentioned radicals are substituted by s radicals selected from the group consisting of halogen and OR 3 ,
R 2 is (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, where the three last-mentioned radicals are substituted by s radicals selected from the group consisting of halogen and OR 3 ,
R 3 is hydrogen or (C 1 -C 6 )-alkyl,
n is 0, 1 or 2, and
s is 0, 1, 2 or 3.
4. The compound or salt as claimed in claim 1 , wherein
R is hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl,
X and Z independently of one another are in each case nitro, halogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 6 )-cycloalkyl, OR 1 , S(O) n R 2 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 or 1,2,4-triazol-1-yl,
Y is S(O) n R 2 , 4,5-dihydro-1,2-oxazol-3-yl, 5-cyanomethyl-4,5-dihydro-1,2-oxazol-3-yl or 5-methoxymethyl-4,5-dihydro-1,2-oxazol-3-yl,
R 1 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl or phenyl-(C 1 -C 6 )-alkyl, where the seven last-mentioned radicals are substituted by s radicals selected from the group consisting of halogen and OR 3 ,
R 2 is (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, where the three last-mentioned radicals are substituted by s radicals selected from the group consisting of halogen and OR 3 ,
R 3 is hydrogen or (C 1 -C 6 )-alkyl,
n is 0, 1 or 2, and
s is 0, 1, 2 or 3.
5. A herbicidal composition which comprises a herbicidally effective amount of at least one compound of the formula (I) or salt as claimed in claim 1 .
6. The herbicidal composition as claimed in claim 5 comprising a mixture with at least one formulation auxiliary.
7. The herbicidal composition as claimed in claim 5 , comprising at least one further pesticidally active compound selected from the group consisting of the insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.
8. The herbicidal composition as claimed in claim 7 , comprising a safener.
9. The herbicidal composition as claimed in claim 7 , comprising a further herbicide.
10. A method of controlling undesired plants comprising applying an effective amount of at least one compound of the formula (I) or salt as claimed in claim 1 to a plant to a location of undesired plant growth.
11. The method of claim 10 , wherein the compound of the formula (I) or salt is capable of being used for controlling unwanted plants in crops of useful plants.
12. The method of claim 11 , wherein the useful plants are transgenic useful plants.
13. A compound of the formula (I) and/or a salt thereof
in which
R is methyl,
X is Cl,
Y is CH 2 OCH 2 CF 3 , and
Z is SO 2 Me.
14. The compound and/or salt as claimed in claim 1 , wherein
R is (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, or cyano.
15. The compound and/or salt as claimed in claim 1 , wherein
R is (C 1 -C 6 )-alkyl.