N-(1,2,5-Oxadiazol-3-yl)-, N-(tetrazol-5-yl)- and N-(triazol-5-yl)bicycloarylcarboxamides and their use as herbicides
View Patent ↗N-(1,2,5-Oxadiazol-3-yl)-, N-(tetrazol-5-yl)- and N-(triazol-5-yl)bicycloarylcarboxamides of the general formula (I) are described as herbicides. In this formula (I), R 3 , R 4 and R 5 are each radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. Q is a heterocycle. X and Y are each oxygen and sulfur.
1. An N-(1,2,5-oxadiazol-3-yl)-, N-(tetrazol-5-yl)- or N-(triazol-5-yl)bicycloarylcarboxamide of the formula (I) or a salt thereof
in which
Q is a Q1, Q2 or Q3 radical,
R 1 is (C 1 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, 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, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 - C 6 ) - alkoxy-(C 2 -C 6 )-alkenyl, (C 1 -C 6 )-alkoxy-(C 2 -C 6 )-alkynyl, CH 2 R 6 , heteroaryl, heterocyclyl or phenyl, where the three latter radicals are each substituted by u 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, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-alkylsulfinyl, (C 1 -C 6 )-alkylsulfonyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy and (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl;
R 2 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, halo-(C 2 -C 6 )-alkenyl, (C 2 - C 6 )-alkynyl, (C 2 -C 6 )-alkynyloxy, halo-(C 2 -C 6 )-alkynyl, 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 substituted by u radicals selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen;
R 3 and R 4 are each independently hydrogen, (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, (C 3 -C 7 )-cycloalkyl, (C 3 -C 7 )-halocycloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-haloalkylthio, (C 1 -C 6 )-alkylsulfinyl, (C 1 -C 6 )-haloalkylsulfinyl, (C 1 -C 6 )-alkylsulfonyl, (C 1 -C 6 )-haloalkylsulfonyl, (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl, halogen, nitro or cyano;
R 5 is hydrogen or fluorine;
R 6 is acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenz-amido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, (C 3 -C 6 )-cycloalkyl, or heteroaryl, heterocyclyl or phenyl each substituted by u radicals selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen;
R 7 and R 8 are each independently hydrogen, (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, (C 3 -C 7 )-cycloalkyl, halo-(C 3 -C 7 ) -cycloalkyl, -OR 9 , S(O) m R 9 , (C 1 -C 6 )-alkylthio, halo-(C 1 -C 6 )-alkylthio, (C 1 -C 6 )-alkylsulfinyl, halo-(C 1 -C 6 )-alkylsulfinyl, (C 1 -C 6 )-alkylsulfonyl, halo-(C 1 -C 6 )-alkyl-sulfonyl, (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl, halogen, nitro, cyano, heteroaryl, heterocyclyl or phenyl, where the three latter radicals are each substituted by u radicals selected from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-alkylsulfinyl, (C 1 -C 6 )-alkylsulfonyl, (C 1 - C 6 ) - alkoxy, halo-(C 1 -C 6 )-alkoxy and (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl,
or
R 7 and R 8 together with the carbon atom to which they are bonded form a —X 1 —(CH 2 ) r —X 2 —, —(CH 2 ) s —X 3 —, —(CH 2 ) t —X 3 —CH 2 —, —(CH 2 ) v —X 3 —CH 2 CH 2 — or —(CH 2 ) w — unit in which each of the (CH 2 ) groups is substituted by m radicals selected from the group consisting of halogen, methyl and (C 1 -C 3 )-alkoxy,
or
R 7 and R 8 together with the carbon atom to which they are bonded form the —O—N((C 1 -C 3 )-alkyl)-CHR 10 —CH 2 — or —O—N═CR 10 —CH 2 — unit in which each of the (CH 2 ) groups is substituted by m radicals selected from the group consisting of halogen and methyl;
R 9 is hydrogen, (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, (C 3 -C 7 )-cycloalkyl, (C 3 -C 7 )-halocycloalkyl, (C 3 -C 7 )-cycloalkyl-(C 1 -C 3 )-alkyl, halo-(C 3 -C 7 )-cycloalkyl-(C 1 -C 3 )-alkyl, heteroaryl, heterocyclyl or phenyl, where the three latter radicals are each substituted by s radicals selected from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 ) -alkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-alkylsulfinyl, (C 1 -C 6 )-alkylsulfonyl, (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 3 )-alkyl, or phenyl substituted by u radicals selected from the group Consisting of (C 1 -C 3 )-alkyl, halogen, cyano and nitro;
R 11 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, formyl, (C 2 -C 6 )-alkylcarbonyl, (C 2 -C 6 )-alkoxycarbonyl or (C 1 -C 2 )-alkylsulfonyl;
X and Y are independently O, S, SO, SO 2 , C═O, C═S, NR 10 , CR 7 R 8 , C═NOR 10 or C═NN(R 11 ) 2 ;
X 1 and X 2 are each independently O, S or N((C 1 -C 3 )-alkyl);
X 3 is O or S;
m is 0, 1 or 2;
n is 2;
r is 2, 3 or 4;
s is 2, 3, 4 or 5;
t is 1, 2, 3 or 4;
u is 0, 1, 2 or 3;
v is 2 or 3; and
w is 2, 3, 4, 5 or 6.
2. An N-(1,2,5-oxadiazol-3-yl)—, N-(tetrazol-5-yl)- or N-(triazol-5-yl)bicycloarylcarboxamide as claimed in claim 1 , in which
R 1 is (C 1 -C 3 )-alkyl, (C 3 -C 5 )-cycloalkyl, halo-(C 1 -C 3 )-alkyl or (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl;
R 2 is hydrogen, (C 1 -C 3 )-alkyl, (C 3 -C 5 )-cycloalkyl, halo-(C 1 -C 3 )-alkyl, (C 1 -C 3 )-alkoxy, halo-(C 1 -C 3 )-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, methoxycarbonyl, ethoxycarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl or methoxymethyl;
R 3 and R 4 are each independently hydrogen, (C 1 -C 3 )-alkyl, halo-(C 1 -C 3 )-alkyl, (C 3 -C 5 )-cycloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-alkylsulfinyl, (C 1 -C 6 )-alkylsulfonyl, (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl, halogen, nitro or cyano;
R 5 is hydrogen;
R 7 and R 8 are each independently hydrogen, (C 1 -C 3 )-alkyl, halo-(C 1 -C 3 )-alkyl, (C 3 -C 5 )-cycloalkyl, —OR 9 , —S(O) m R 9 , (C 1 -C 3 )-alkylthio, (C 1 -C 3 )-alkylsulfinyl, (C 1 -C 3 )-alkylsulfonyl, (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl, halogen, nitro, cyano, heteroaryl, heterocyclyl or phenyl, where the three latter radicals are each substituted by u radicals selected from the group consisting of halogen, nitro, cyano, (C 1 -C 3 )-alkyl, halo-(C 1 -C 3 )-alkyl, (C 3 -C 5 )-cycloalkyl, (C 1 -C 3 )-alkylthio, (C 1 -C 3 )-alkylsulfinyl, (C 1 -C 3 )-alkylsulfonyl, (C 1 -C 3 )-alkoxy, halo-(C 1 -C 3 )-alkoxy and (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl,
or
R 7 and R 8 together with the carbon atom to which they are bonded form a —X 1 —(CH 2 ),—X 2 —, —(CH 2 ) s ,—X 3 —, —(CH 2 ) t —X 3 —CH 2 —, —(CH 2 ) v —X 3 —CH 2 CH 2 — or —(CH 2 ) w — unit in which each of the (CH 2 ) groups is substituted by m radicals selected from the group consisting of halogen, methyl and (C 1 -C 3 )-alkoxy,
or
R 7 and R 8 together with the carbon atom to which they are bonded form the —O—N((C 1 -C 3 )-alkyl)-CHR 10 —CH 2 — or —O—N═CR 10 —CH 2 — unit in which each of the (CH 2 ) groups is substituted by m radicals selected from the group consisting of halogen and methyl;
R 9 is hydrogen, (C 1 -C 3 )-alkyl, halo-(C 1 -C 3 )-alkyl, (C 2 -C 3 )-alkenyl, (C 2 -C 4 )-alkynyl, (C 3 -C 5 )-cycloalkyl, (C 3 -C 5 )-cycloalkyl-(C 1 -C 3 )-alkyl, heteroaryl, heterocyclyl or phenyl, where the three latter radicals are each substituted by s radicals selected from the group consisting of halogen, nitro, cyano, (C 1 -C 3 )-alkyl, halo-(C 1 -C 3 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 3 )-alkylthio, (C 1 -C 3 )-alkylsulfinyl, (C 1 -C 3 )-alkylsulfonyl, (C 1 -C 3 )-alkoxy, halo-(C 1 -C 3 )-alkoxy and (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl;
R 10 is hydrogen or (C 1 -C 3 )-alkyl;
X and Y are each independently O, SO 2 , C═O, C═S, CR 7 R 8 , C═NOR 10 ;
X 1 and X 2 are each independently O, S, N(CH 3 );
X 3 is O or S;
m is 0, 1 or 2;
n is 2;
r is2or3;
s is 2, 3 or 4;
t is 1, 2 or 3;
u is 0, 1 or 2;
v is 2 or 3; and
w is2,3,4or5.
3. A herbicidal composition, comprising a herbicidally active content of at least one compound of the formula (I) as claimed in claim 1 .
4. The herbicidal composition as claimed in claim 3 , in a mixture with at least one formulation auxiliary.
5. A herbicidal composition as claimed in claim 3 additionally comprising at least one pesticidally active substance selected from the group consisting of an insecticide, an acaricide, a further herbicide, a fungicide, a safener and a growth regulator.
6. The herbicidal composition as claimed in claim 5 , comprising a safener.
7. A herbicidal composition as claimed in claim 6 , comprising cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.
8. A herbicidal composition as claimed in claim 5 , comprising a further herbicide.
9. The compound of formula (I) and/or a salt thereof as claimed in claim 1 capable of being used for controlling an unwanted plant.
10. The compound of formula (I) and/or a salt thereof as claimed in claim 1 , wherein said compound of formula (I) is capable of being used for controlling an unwanted plant in a crop of a useful plant.
11. The compound of formula (I) capable of being used as claimed in claim 10 , wherein said useful plant is a transgenic useful plant.
12. The compound of formula (I) and/or a salt thereof as claimed in claim 2 , capable of being used for controlling an unwanted plant.
13. A herbicidal composition as claimed in claim 3 capable of being used for controlling an unwanted plant.
14. An N-(tetrazol-5-yl)bicycloarylcarboxamide as claimed in claim 1 having the formula
15. An N-(tetrazol-5-yl)bicycloarylcarboxamide as claimed in claim 1 having the formula
16. An N-(tetrazol-5-yl)bicycloarylcarboxamide as claimed in claim 1 having the formula
17. An N-(tetrazol-5-yl)bicycloarylcarboxamide as claimed in claim 1 having the formula
18. An N-(tetrazol-5-yl)bicycloarylcarboxamide as claimed in claim 1 having the formula