Substituted thiene-3-ylsulphonylamino(thio)carbonyl-triazolin(thi)ones

1. A compound of formula (I)

or salts thereof,

in which

Q 1 represents O,

Q 2 represents O,

R 1 represents optionally cyano-, halogen-, or C 1 -C 4 -alkoxy-substituted alkyl having 1 to 6 carbon atoms; represents optionally cyano- or halogen-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms; or represents optionally cyano-, halogen-, or C 1 -C 4 -alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl group and, optionally, 1 to 4 carbon atoms in the alkyl moiety,

R 2 represents hydrogen, cyano, nitro, or halogen; represents optionally cyano-, halogen-, or C 1 -C 4 -alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, or alkylsulfonyl having in each case 1 to 6 carbon atoms in the alkyl group; or represents optionally cyano- or halogen-substituted alkenyl, alkynyl, alkenyloxy, or alkynyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkynyl group,

R 3 represents halogen-substituted alkoxy having 1 to 6 carbon atoms, and

R 4 represents hydrogen, hydroxy, amino, or cyano; represents C 2 -C 10 -alkylideneamino; represents optionally fluorine-, chlorine-, bromine-, cyano-, C 1 -C 4 -alkoxy-, C 1 -C 4 -alkyl-carbonyl-, or C 1 -C 4 -alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms; represents optionally fluorine-, chlorine-, and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms; represents optionally fluorine-, chlorine-, bromine-, cyano-, C 1 -C 4 -alkoxy-, or C 1 -C 4 -alkoxy-carbonyl-substituted alkoxy, alkylamino or alkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkyl groups; represents alkenyloxy having 3 to 6 carbon atoms; represents dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups;or represents optionally fluorine-, chlorine-, bromine-, cyano-, and/or C 1 -C 4 -alkyl-substituted cycloalkyl, cycloalkylamino, or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the alkyl group and, optionally, 1 to 4 carbon atoms in the alkyl moiety.

2. A compound according to claim 1 in which

R 1 represents optionally cyano-, fluorine-, chlorine-, methoxy-, or ethoxy-substituted methyl, ethyl, n- or isoproyl, or n-, iso-, s-, or t-butyl; represents optionally cyano-, fluorine-, or chlorine-substituted propenyl, butenyl, propynyl, or butynyl; represents optionally cyano-, fluorine-, chlorine-, methyl-, or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, or cyclohexylmethyl,

R 2 represents hydrogen, cyano, fluorine, chlorine, or bromine; represents optionally cyano-, fluorine-i chlorine-, methoxy-, or ethoxy-substituted methyl, ethyl, n- or isopropyl, n-, iso-, s-, or t-butyl, methoxy, ethoxy, n- or isopropoxy, methoxycarbonyl, ethoxycarbonyl, n- or isopropoxycarbonyl, methylthio, ethylthio, n- or isopropylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, or ethylsulfonyl; or represents optionally cyano-, fluorine-, or chlorine-substituted propenyl, butenyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy, or butynyloxy,

R 3 represents fluorine- or chlorine-substituted methoxy, ethoxy, n- or isopropoxy, n-, iso-, s- or t-butoxy, n-, iso-, s-, or t-pentyloxy, or neopentyloxy, and

R 4 represents hydrogen, hydroxy, or amino; represents optionally fluorine-, chlorine-, cyano-, methoxy-, or ethoxy-substituted methyl, ethyl, n- or isopropyl, or n-, iso-, s-, or t-butyl; represents optionally fluorine-, chlorine-, and/or bromine-substituted ethenyl, propenyl, butenyl, propynyl, or butynyl; represents optionally fluorine-, chlorine-, cyano-, methoxy-, or ethoxy-substituted methoxy, ethoxy, n- or isopropoxy, n-, iso-, s-, or t-butoxy, methylamino, ethylamino, n- or isopropylamino, or n-, iso-, s-, or t-butylamino; represents propenyloxy or butenyloxy; represents dimethylamino or diethyl-amino; or represents optionally fluorine-, chlorine-, methyl-, and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutyl methyl, cyclopentyl methyl, or cyclohexylmethyl.

3. A compound according to claim 1 in which

R 1 represents optionally fluorine-, chlorine-, methoxy-, or ethoxy-substituted methyl, ethyl, or n- or isopropyl,

R 2 represents fluorine, chlorine, or bromine; or represents optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, or n- or isopropyl,

R 3 represents fluorine- or chlorine-substituted methoxy, ethoxy, n- or isopropoxy, n-, iso-, s-, or t-butoxy, n-, iso-, s-, or t-pentyloxy, or neopentyloxy, and

R 4 represents optionally fluorine-, chlorine-, methoxy-, or ethoxy-substituted methyl, ethyl, or n- or isopropyl; represents optionally fluorine- or chlorine-substituted ethenyl, propenyl, or propynyl; represents optionally fluorine-, chlorine-, methoxy-, or ethoxy-substituted methoxy, ethoxy, or n- or isopropoxy; represents methylamino; or represents cyclopropyl.

4. A compound according to claim 3 in which R 1 represents methyl.

5. A compound according to claim 3 in which R 1 represents ethyl.

6. A compound according to claim 3 in which R 1 represents n-propyl.

7. A compound according to claim 3 in which R 1 represents isopropyl.

8. A process for preparing a compound according to claim 1 comprising

(a) reacting a substituted thiophene-3-sulphonamide of formula (II)

in which R 1 and R 2 are as defined for formula (I) of claim 1 , with a substituted triazolinone of formula (III)

in which

Q 1 , Q 2 , R 3 , and R 4 are as defined for formula (I) of claim 1 , and

Z represents halogen, alkoxy, aryloxy, or arylalkoxy, optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent, or

(b) reacting a substituted thiene-3-ylsulphonyl iso(thio)cyanate of formula (IV)

in which Q 1 , R 1 , and R 2 are as defined for formula (I) of claim 1 , with a triazolinone of formula (V)

in which Q 2 , R 4 , and R 5 are as defined for formula (I) of claim 1 , optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent, or

(c) reacting a substituted thiophene-3-sulphonyl chloride of formula (VI)

in which R 1 and R 2 are as defined for formula (I) of claim 1 , with a triazolinone of formula (V)

in which Q 2 , R 4 , and R 5 are as defined for formula (I) of claim 1 , and a metal cyanate of formula (VII)

M-Q 1 -CN  (VII)

in which Q 1 is as defined for formula (I) of claim 1 , optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent, or

(d) reacting a substituted thiophene-3-sulphonyl chloride of formula (VI)

in which R 1 and R 2 are as defined for formula (I) of claim 1 , with a triazolinone carboxamide of formula (VIII)

in which Q 1 , Q 2 , R 3 , and R 4 are as defined for formula (I) of claim 1 , optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent, or

(e) reacting a substituted thiene-3-yl-sulphonylaminocarbonyl compound of formula (IX)

in which

Q 1 , R 1 , and R 2 are as defined for formula (I) of claim 1 , and

Z represents halogen, alkoxy, aryloxy, or arylalkoxy, with a triazolinone of formula (V)

in which Q 2 , R 4 , and R 5 are as defined for formula (I) of claim 1 , optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent.

9. A process according to claim 8 additionally comprising converting a compound of formula (I) prepared according claim 8 to a salt thereof.

10. A herbicidal composition comprising a compound according to claim 1 and one or more extenders and/or surfactants.

11. A method for controlling unwanted vegetation comprising allowing an effective amount of one or more compounds according to claim 1 to act on an unwanted plant and/or its habitat.

12. A compound according to claim 1 in which

Q 1 represents O,

Q 2 represents O,

R 1 represents alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms,

R 2 represents alkyl having 1 to 6 carbon atoms,

R 3 represents halogen-substituted alkoxy having 1 to 6 carbon atoms, and

R 4 represents alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms.