Herbicidally active 4-(3-alkylsulfinylbenzoyl)pyrazoles
View Patent ↗4-(3-Alkylsulfinylbenzoyl)pyrazoles of the formula (I) are described as herbicides. In this formula (I), R 1 to R 4 , X and Y are radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen.
1. A 4-(3-alkylsulfinylbenzoyl)pyrazole of the formula (I) or a salt thereof
in which
R 1 is (C 1 -C 4 )-alkyl,
R 2 is hydrogen or (C 1 -C 4 )-alkyl,
R 3 is (C 1 -C 6 )-alkyl,
R 4 is hydrogen, (C 1 -C 6 )-alkylsulfonyl, (C 1 -C 4 )-alkoxy -(C 1 -C 6 )-alkylsulfonyl, or is phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C 1 -C 6 )-alkyl or benzyl, each of which is substituted by m identical or different radicals from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy,
X is hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, (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, OR 5 , OCOR 5 , OSO 2 R 5 , S(O) n R 5 , SO 2 OR 5 , SO 2 N(R 5 ) 2 , NR 5 SO 2 R 5 , NR 5 COR 5 , (C 1 -C 6 )-alkyl-S(O) n R 5 , (C 1 -C 6 )-alkyl-OR 5 , (C 1 -C 6 )-alkyl-OCOR 5 , (C 1 -C 6 )-alkyl-OSO2R 5 , (C 1 -C 6 ) -alkyl-SO 2 OR 5 , (C 1 -C 6 )-alkyl-SO 2 N(R 5 ) 2 or (C 1 -C 6 )-alkyl-NR 5 COR 5 ;
Y is fluorine, chlorine, bromine, iodine, nitro or the group SO 2 R 7 ,
R 5 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, phenyl or phenyl-(C 1 -C 6 )-alkyl, where the six last-mentioned radicals are substituted by s radicals from the group consisting of hydroxy, mercapto, amino, cyano, nitro, thiocyanato, OR 6 , SR 6 , N(R 6 ) 2 , NOR 6 , OCOR 6 , SCOR 6 , NR 6 COR 6 , CO 2 R 6 , COSR 6 , CON(R 6 ) 2 , (C 1 )-C 4 -alkyliminooxy, (C 1 -C 4 ) -alkylcarbonyl, (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl and (C 1 -C 4 ) -alkylsulfonyl;
R 6 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl,
R 7 is (C 1 -C 4 )-alkyl,
m is 0, 1, 2, 3, 4 or 5,
n is 0, 1 or 2,
s is 0, 1, 2 or 3.
2. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which
R 1 is methyl, ethyl, n-propyl or isopropyl,
R 2 is hydrogen, methyl, ethyl, n-propyl or isopropyl,
R 3 is (C 1 -C 4 )-alkyl,
R 4 is hydrogen, (C 1 -C 3 )-alkylsulfonyl, (C 1 -C 2 )-alkoxy -(C 1 -C 4 )-alkylsulfonyl, or is phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C 1 -C 6 )-alkyl or benzyl, each of which is substituted by m methyl groups,
X is nitro, halogen, (C 1 -C 4 )-alkyl, trifluoromethyl, (C 1 -C 4 ) -alkoxy, methylsulfonyl, methoxymethyl, methoxymethoxymethyl, ethoxyethoxymethyl, ethoxymethoxymethyl, methoxyethoxymethyl, methoxypropoxymethyl, methylsulfonylmethyl, methylsulfonylethoxymethyl, methoxyethylsulfonylmethyl, methylsulfonylethylsulfonylmethyl,
Y is fluorine, chlorine, bromine, iodine or the group SO 2 R 7 ,
R 7 is methyl, ethyl, n-propyl or isopropyl,
m is 0, 1, 2 or 3.
3. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which
R 1 is methyl or ethyl,
R 2 is hydrogen, methyl or ethyl,
R 3 is methyl, ethyl, n-propyl or isopropyl,
R 4 is hydrogen,
X is nitro, halogen, (C 1 -C 4 )-alkyl, trifluoromethyl, (C 1 -C 4 ) -alkoxy, methylsulfonyl, methoxymethyl, methoxymethoxymethyl, ethoxyethoxymethyl, ethoxymethoxymethyl, methoxyethoxymethyl, methoxypropoxymethyl, methylsulfonylmethyl, methylsulfonylethoxymethyl, methoxyethylsulfonylmethyl, methylsulfonylethylsulfonylmethyl,
Y is fluorine, chlorine, bromine, iodine or the group SO 2 R 7 ,
R 7 is methyl or ethyl.
4. A herbicidal composition which comprises a herbicidally active amount of at least one compound of the formula (I) as claimed in claim 1 .
5. The herbicidal composition as claimed in claim 4 in a mixture with formulation auxiliaries.
6. A method of controlling unwanted plants, which comprises applying an effective amount of at least one compound of the formula (I) as claimed in claim 1 to plants and/or to a location of unwanted plant growth.
7. A compound of the formula (I) as claimed in claim 1 capable of controlling unwanted plants.
8. A method for using a compound as claimed in claim 7 , wherein a compound of the formula (I) is employed for controlling unwanted plants in crops of useful plants.
9. A method as claimed in claim 8 , wherein the useful plants are transgenic useful plants.
10. A method for making a herbicidically active 4-(3-alkylsulfinylbenzol) pyrazole as claimed in claim 1 comprising reacting a compound of formula (II),
with a pyrazole,
in which
R 3 is (C 1 -C 6 )-alkyl
X is hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, (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, OR 5 , OCOR 5 , OSO 2 R 5 ,S(O) n R 5 , SO 2 OR 5 ,SO 2 N(R 5 ) 2 ,NR 5 SO 2 R 5 , NR 5 COR 5 , (C 1 -C 6 )-alkyl-S(O) n R 5 , (C 1 -C 6 )-alkyl-OR 5 , (C 1 -C 6 )-alkyl-OCOR 5 , (C 1 -C 6 )-alkyl-OSO2R 5 , (C 1 -C6) -alkyl-SO 2 OR 5 , (C 1 -C 6 )-alkyl-SO 2 N(R 5 ) 2 or (C 1 -C 6 )-alkyl-NR 5 COR 5 ;
Y is fluorine, chlorine, bromine, iodine, nitro or the group SO 2 R 7 .
11. A compound of formula (Ia) or a salt thereof
12. A herbicidal composition, comprising a herbicidally active amount of at least one compound of formula (Ia) or salt as claimed in claim 11 .
13. The herbicidal composition as claimed in claim 12 in a mixture with formulation auxillaries.
14. A method of controlling undesired plants, comprising applying an effective amount of at least one compound of the formula (Ia) as claimed in claim 11 to plants and/or to a location of unwanted plant growth.
15. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which
R l is methyl or ethyl,
R 2 is hydrogen,
R 3 is methyl, ethyl, n-propyl or isopropyl,
R 4 is hydrogen,
X is methyl, chlorine, or methoxymethyl,
Y is chlorine, bromine, or the group SO 2 R 7 ,
R 7 is methyl.
16. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which
R 2 is (C 1 -C 4 )-alkyl.
17. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which
R 4 is (C 1 -C 6 )-alkylsulfonyl, (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkylsulfonyl, or is phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C 1 -C 6 )-alkyl or benzyl, each of which is substituted by m identical or different radicals from the group consisting of halogen, (C 1 -C 4 ) -alkyl and (C 1 -C 4 )-alkoxy.
18. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which
X is hydrogen, mercapto, nitro, fluorine, bromine, iodine, cyano, thiocyanato, (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, OR 5 , OCOR 5 , OSO 2 R 5 , S(O) n R 5 , SO 2 OR 5 , SO 2 N(R 5 ) 2 , NR 5 SO 2 R 5 , NR 5 COR 5 , (C 1 -C 6 )-alkyl -S(O) n R 5 , (C 1 -C 6 )-alkyl-OR 5 , (C 1 -C 6 )-alkyl -OCOR 5 , (C 1 -C 6 )-alkyl-OSO2R 5 , (C 1 -C 6 )-alkyl -SO 2 OR 5 , (C 1 -C 6 )-alkyl-SO 2 N(R 5 ) 2 or (C 1 -C 6 )-alkyl-NR 5 COR 5 .
19. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which
Y is fluorine, chlorine, bromine, iodine, or nitro.