SUBSTITUTED 4-HETEROARYLOXYPYRIDINES AND SALTS THEREOF AND THEIR USE AS HERBICIDAL AGENTS

Abstract

Substituted 4-heteroaryloxypyridines and salts thereof and use thereof as herbicidal active substances Substituted 4-heteroaryloxypyridines of the general formula (I) are described,

##STR00001##

and their use as herbicides, in particular for controlling broad-leaved weeds and/or weed grasses in crops of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants. The present invention further relates to herbicidal and/or plant growth-regulating compositions comprising one or more compounds of the general formula (I).

Claims

1. A substituted 4-heteroaryloxypyridine of formula (I) or a salt thereof ##STR00020## in which X represents nitrogen or —CH—, A represents oxygen, —S(O).sub.n—, —C(R.sup.4)(R.sup.5)—, —C(═O)— or —NR.sup.6— with n=0, 1 or 2, R.sup.1 represents optionally substituted aryl, heteroaryl, heterocylyl, (C.sub.3-C.sub.10)-cycloalkyl or (C.sub.3-C.sub.10)-cycloalkenyl, where each ring or each ring system is optionally substituted by up to 5 substituents independently of one another selected from the group R.sup.7, R.sup.2 independently of the others represents halogen, cyano, nitro, formyl, formamide, (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.2-C.sub.8)-haloalkynyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulfinyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulfonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.8)-alkylcarbonyl, (C.sub.1-C.sub.8)-haloalkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkylcarbonyl, carboxyl, (C.sub.1-C.sub.8)-alkoxycarbonyl, (C.sub.1-C.sub.8)-haloalkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkoxycarbonyl, carbamoyl, (C.sub.2-C.sub.8)-alkylaminocarbonyl, (C.sub.2-C.sub.10)-dialkylaminocarbonyl, (C.sub.3-C.sub.10)-cycloalkylaminocarbonyl, (C.sub.1-C.sub.4)-alkoxycarbonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkoxycarbonyl-(C.sub.1-C.sub.4)-alkyl, carboxy-(C.sub.1-C.sub.4)-alkyl, hydroxy, amino, (C.sub.1-C.sub.8)-alkoxy, (C.sub.1-C.sub.8)-haloalkoxy, (C.sub.1-C.sub.8)-alkylthio, (C.sub.1-C.sub.8)-haloalkylthio, (C.sub.3-C.sub.8)-cycloalkylthio, (C.sub.1-C.sub.8)-alkylsulfinyl, (C.sub.1-C.sub.8)-haloalkylsulfinyl, (C.sub.3-C.sub.8)-cycloalkylsulfinyl, (C.sub.1-C.sub.8)-alkylsulfonyl, (C.sub.1-C.sub.8)-haloalkylsulfonyl, (C.sub.3-C.sub.8)-cycloalkylsulfonyl, (C.sub.1-C.sub.8)-alkylaminosulfonyl, (C.sub.2-C.sub.8)-dialkylaminosulfonyl or (C.sub.3-C.sub.8)-trialkylsilyl, m represents 0, 1, 2 or 3, R.sup.3 represents hydrogen, halogen, cyano, nitro, formyl, (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.2-C.sub.8)-haloalkynyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulfinyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulfonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.8)-alkylcarbonyl, (C.sub.1-C.sub.8)-haloalkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkylcarbonyl, carboxyl, (C.sub.1-C.sub.8)-alkoxycarbonyl, (C.sub.1-C.sub.8)-haloalkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkoxycarbonyl, (C.sub.1-C.sub.8)-alkylaminocarbonyl, (C.sub.2-C.sub.8)-dialkylaminocarbonyl, (C.sub.3-C.sub.8)-cycloalkylaminocarbonyl, hydroxy, (C.sub.1-C.sub.8)-alkoxy, (C.sub.1-C.sub.8)-haloalkoxy, (C.sub.1-C.sub.8)-alkylthio, (C.sub.1-C.sub.8)-haloalkylthio, (C.sub.3-C.sub.8)-cycloalkylthio, (C.sub.1-C.sub.8)-alkylsulfinyl, (C.sub.1-C.sub.8)-haloalkylsulfinyl, (C.sub.3-C.sub.8)-cycloalkylsulfinyl, (C.sub.1-C.sub.8)-alkylsulfonyl, (C.sub.1-C.sub.8)-haloalkylsulfonyl, (C.sub.3-C.sub.8)-cycloalkylsulfonyl, (C.sub.1-C.sub.8)-alkylaminosulfonyl, (C.sub.2-C.sub.8)-dialkylaminosulfonyl or (C.sub.3-C.sub.8)-trialkylsilyl, R.sup.4 and R.sup.5 independently of one another represent hydrogen, hydroxy, halogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulfinyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulfonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.8)-alkylcarbonyl, (C.sub.1-C.sub.8)-haloalkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkylcarbonyl, (C.sub.1-C.sub.8)-alkoxycarbonyl, (C.sub.1-C.sub.8)-haloalkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkoxycarbonyl, (C.sub.1-C.sub.8)-alkylaminocarbonyl, (C.sub.2-C.sub.8)-dialkylaminocarbonyl, (C.sub.3-C.sub.8)-cycloalkylaminocarbonyl, (C.sub.1-C.sub.8)-alkoxy, (C.sub.1-C.sub.8)-alkylthio, (C.sub.1-C.sub.8)-haloalkylthio, (C.sub.3-C.sub.8)-cycloalkylthio, or R.sup.4 and R.sup.5 together form a 3- to 6-membered carbocyclic ring or a 3- to 6-membered saturated heterocyclic ring having up to 2 oxygen atoms, or R.sup.4 and R.sup.5 together form a (C.sub.1-C.sub.3)-alkylidene radical or (C.sub.1-C.sub.3)-haloalkylidene radical, R.sup.6 represents hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, aryl-(C.sub.1-C.sub.6)-alkyl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-halocycloalkyl, (C.sub.3-C.sub.6)-halocycloalkyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulfinyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulfonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.8)-alkylcarbonyl, (C.sub.1-C.sub.8)-haloalkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkylcarbonyl, formyl, (C.sub.1-C.sub.8)-alkoxycarbonyl, (C.sub.1-C.sub.8)-haloalkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkoxycarbonyl, (C.sub.1-C.sub.8)-alkylaminocarbonyl, (C.sub.2-C.sub.8)-dialkylaminocarbonyl, (C.sub.3-C.sub.8)-cycloalkylaminocarbonyl, and R.sup.7 represents hydrogen, halogen, cyano, nitro, formyl, (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.2-C.sub.8)-haloalkynyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulfinyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulfonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.8)-alkylcarbonyl, (C.sub.1-C.sub.8)-haloalkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkylcarbonyl, carboxyl, (C.sub.1-C.sub.8)-alkoxycarbonyl, (C.sub.1-C.sub.8)-haloalkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkoxycarbonyl, (C.sub.1-C.sub.8)-alkylaminocarbonyl, (C.sub.2-C.sub.8)-dialkylaminocarbonyl, (C.sub.3-C.sub.8)-cycloalkylaminocarbonyl, hydroxy, (C.sub.1-C.sub.8)-alkoxy, (C.sub.1-C.sub.8)-haloalkoxy, (C.sub.1-C.sub.8)-alkylthio, (C.sub.1-C.sub.8)-haloalkylthio, (C.sub.3-C.sub.8)-cycloalkylthio, (C.sub.1-C.sub.8)-alkylsulfinyl, (C.sub.1-C.sub.8)-haloalkylsulfinyl, (C.sub.3-C.sub.8)-cycloalkylsulfinyl, (C.sub.1-C.sub.8)-alkylsulfonyl, (C.sub.1-C.sub.8)-haloalkylsulfonyl, (C.sub.3-C.sub.8)-cycloalkylsulfonyl, (C.sub.1-C.sub.8)-alkylaminosulfonyl, (C.sub.2-C.sub.8)-dialkylaminosulfonyl or (C.sub.3-C.sub.8)-trialkylsilyl.

2. The compound of formula (I) as claimed in claim 1 or a salt thereof, in which X represents nitrogen or —CH—, A represents oxygen, —S(O).sub.n—, —C(R.sup.4)(R.sup.5)—, —C(═O)— or —NR.sup.6— with n=0, 1 or 2, R.sup.1 represents optionally substituted aryl, heteroaryl or heterocylyl, where each of the rings or each ring system is optionally substituted by up to 5 substituents independently selected from the group R.sup.7, R.sup.2 independently of the others represents halogen, cyano, nitro, formyl, formamide, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.2-C.sub.4)-haloalkenyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylcarbonyl, (C.sub.1-C.sub.4)-haloalkylcarbonyl, carboxyl, (C.sub.1-C.sub.4)-alkoxycarbonyl, (C.sub.1-C.sub.4)-haloalkoxycarbonyl, (C.sub.3-C.sub.6)-cycloalkoxycarbonyl, carbamoyl, (C.sub.2-C.sub.4)-alkylaminocarbonyl, (C.sub.2-C.sub.6)-dialkylaminocarbonyl, (C.sub.1-C.sub.4)-alkoxycarbonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkoxycarbonyl-(C.sub.1-C.sub.4)-alkyl, carboxy-(C.sub.1-C.sub.4)-alkyl, hydroxy, amino, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-alkylsulfinyl, (C.sub.1-C.sub.4)-alkylsulfonyl, (C.sub.1-C.sub.4)-alkylaminosulfonyl, (C.sub.2-C.sub.6)-dialkylaminosulfonyl or (C.sub.3-C.sub.6)-trialkylsilyl, m represents 0, 1, 2 or 3, R.sup.3 represents hydrogen, halogen, cyano, nitro, formyl, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.2-C.sub.4)-haloalkenyl, (C.sub.2-C.sub.4)-haloalkynyl, (C.sub.1-C.sub.4)-alkylcarbonyl, (C.sub.1-C.sub.4)-haloalkylcarbonyl, carboxyl, (C.sub.1-C.sub.4)-alkoxycarbonyl, (C.sub.1-C.sub.4)-haloalkoxycarbonyl, (C.sub.3-C.sub.6)-cycloalkoxycarbonyl, (C.sub.1-C.sub.4)-alkylaminocarbonyl, (C.sub.2-C.sub.6)-dialkylaminocarbonyl, hydroxy, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-haloalkylthio, (C.sub.1-C.sub.4)-alkylsulfinyl, (C.sub.1-C.sub.4)-haloalkylsulfinyl, (C.sub.1-C.sub.4)-alkylsulfonyl, (C.sub.1-C.sub.4)-haloalkylsulfonyl, (C.sub.1-C.sub.4)-alkylaminosulfonyl, (C.sub.2-C.sub.6)-dialkylaminosulfonyl or (C.sub.3-C.sub.6)-trialkylsilyl, R.sup.4 and R.sup.5 independently of one another represent hydrogen, hydroxy, halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.1-C.sub.4)-alkoxycarbonyl, (C.sub.1-C.sub.4)-haloalkoxycarbonyl or (C.sub.3-C.sub.6)-cycloalkoxycarbonyl, or R.sup.4 and R.sup.5 together form a (C.sub.1-C.sub.3)-alkylidene radical or (C.sub.1-C.sub.3)-haloalkylidene radical, R.sup.6 represents hydrogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, aryl-(C.sub.1-C.sub.4)-alkyl, heteroaryl-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.1-C.sub.4)-alkylcarbonyl, formyl or (C.sub.1-C.sub.4)-alkoxycarbonyl, and R.sup.7 represents hydrogen, halogen, cyano, nitro, formyl, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.2-C.sub.4)-haloalkenyl, (C.sub.2-C.sub.4)-haloalkynyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylcarbonyl, (C.sub.1-C.sub.4)-haloalkylcarbonyl, carboxyl, (C.sub.1-C.sub.4)-alkoxycarbonyl, (C.sub.1-C.sub.4)-haloalkoxycarbonyl, (C.sub.3-C.sub.6)-cycloalkoxycarbonyl, (C.sub.1-C.sub.4)-alkylaminocarbonyl, (C.sub.2-C.sub.6)-dialkylaminocarbonyl, (C.sub.3-C.sub.6)-cycloalkylaminocarbonyl, hydroxy, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-haloalkylthio, (C.sub.1-C.sub.4)-alkylsulfinyl, (C.sub.1-C.sub.4)-haloalkylsulfinyl, (C.sub.1-C.sub.4)-alkylsulfonyl, (C.sub.1-C.sub.4)-haloalkylsulfonyl, (C.sub.1-C.sub.4)-alkylaminosulfonyl, (C.sub.2-C.sub.6)-dialkylaminosulfonyl or (C.sub.3-C.sub.6)-trialkylsilyl.

3. The compound of formula (I) as claimed in claim 1 or a salt thereof, in which X represents —CH— or nitrogen, A represents oxygen, sulfur, —CH.sub.2— or —NR.sup.6—, R.sup.1 represents an optionally substituted phenyl, pyrid-2-yl or pyrimid-2-yl, where each ring is optionally substituted by up to 5 substituents independently of one another selected from the group R.sup.7, R.sup.2 independently of the others represents fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, carboxylmethyl, m represents 0, 1, 2 or 3, R.sup.3 represents hydrogen, fluorine, chlorine, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy, R.sup.6 represents hydrogen or methyl, and R.sup.7 represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy.

4. A herbicidal composition comprising a herbicidally active amount of at least one compound of formula (I) or salt as claimed in claim 1.

5. The herbicidal composition as claimed in claim 4 in a mixture with one or more formulation auxiliaries.

6. The herbicidal composition as claimed in claim 4, comprising at least one further pesticidally active substance from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners, and growth regulators.

7. The herbicidal composition as claimed in claim 6, comprising a safener.

8. The herbicidal composition as claimed in claim 7, comprising cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.

9. The herbicidal composition as claimed in claim 4, comprising a further herbicide.

10. A method of controlling one or more unwanted plants, comprising applying an effective amount of at least one compound of general formula (I) or salt as claimed in claim 1 or a herbicidal composition thereof to the plants and/or to a site of unwanted vegetation.

11. The compound of formula (I) and/or salt as claimed in claim 1 or a herbicidal composition thereof for controlling one or more unwanted plants.

12. The compound or salt as claimed in claim 11, wherein the compound is used for controlling one or more unwanted plants in one or more crops of one or more useful plants.

13. The compound or salt as claimed in claim 12, wherein the useful plants are transgenic useful plants.

Description

SYNTHESIS EXAMPLES

2,6-Dimethyl-3-(4-fluorophenylthio)-4-(5-chloropyrimidin-2-yloxy)pyridine (Table Example No. 1-26)

[0138] ##STR00010##

[0139] A mixture of 2.4 g (9.6 mmol) of 2,6-dimethyl-3-(4-fluorophenylthio)pyridin-4-ol, 1.3 g (8.7 mmol) of 2,5-dichloropyrimidine and 1.4 g (10 mmol) of K.sub.2CO.sub.3 in 20 ml DMF is heated at 100° C. for 3 h. After cooling, the mixture is diluted with water, the mixture is extracted with dichloromethane, the solvent is evaporated and the residue is purified by column chromatography. The yield is 999 mg (29% of theory).

Synthesis of the precursor 2,6-dimethyl-3-(4-fluorophenylthio)pyridin-4-ol

[0140] A mixture of 2.49 g (10 mmol) of 2,6-dimethyl-3-iodopyridin-4-ol, 1.53 g (12 mmol) of 4-fluorothiophenol, 4.14 g (30 mmol) of K.sub.2CO.sub.3 and 760 mg (4 mmol) of copper(I) thiophene-2-carboxylate in 40 ml of DMF is heated at 110° C. for 3 h. After cooling, the mixture is diluted with 2N hydrochloric acid. The resulting precipitate is filtered off with suction and washed with water and a little ethyl acetate. The yield is 2.4 g.

[0141] In analogy to the preparation examples cited above and recited at the appropriate point, the compounds of the general formula (I) specified hereinafter and shown in Table 1 are obtained.

##STR00011##

TABLE-US-00001 TABLE 1 Ex- ample num- ber R.sup.2a R.sup.2b R.sup.2c R.sup.3 X AR.sup.1 1-1 Me Me H H N 4-fluorophenoxy 1-2 Me Me H H N 3,4-difluorophenoxy 1-3 Me Me H H N 3-(trifluoromethyl)phenoxy 1-4 Me Me H H N 3-methoxyphenoxy 1-5 Me Me H H N 4-cyanophenoxy 1-6 Me Me H F N 4-fluorophenoxy 1-7 Me Me H F N 3,4-difluorophenoxy 1-8 Me Me H F N 3-(trifluoromethyl)phenoxy 1-9 Me Me H F N 3-methoxyphenoxy 1-10 Me Me H F N 4-cyanophenoxy 1-11 Me Me H Cl N 4-fluorophenoxy 1-12 Me Me H Cl N 3,4-difluorophenoxy 1-13 Me Me H Cl N 3-(trifluoromethyl)phenoxy 1-14 Me Me H Cl N 3-methoxyphenoxy 1-15 Me Me H Cl N 4-cyanophenoxy 1-16 Me Me H H N 4-fluorophenylthio 1-17 Me Me H H N 3,4-difluorophenylthio 1-18 Me Me H H N 3-(trifluoromethyl)phenyl- thio 1-19 Me Me H H N 3-methoxyphenylthio 1-20 Me Me H H N 4-cyanophenylthio 1-21 Me Me H F N 4-fluorophenylthio 1-22 Me Me H F N 3,4-difluorophenylthio 1-23 Me Me H F N 3-(trifluoromethyl)phenyl- thio 1-24 Me Me H F N 3-methoxyphenylthio 1-25 Me Me H F N 4-cyanophenylthio 1-26 Me Me H Cl N 4-fluorophenylthio 1-27 Me Me H Cl N 3,4-difluorophenylthio 1-28 Me Me H Cl N 3-(trifluoromethyl)phenyl- thio 1-29 Me Me H Cl N 3-methoxyphenylthio 1-30 Me Me H Cl N 4-cyanophenylthio 1-31 Me Me H H N 4-fluorophenylamino 1-32 Me Me H H N 3,4-difluorophenylamino 1-33 Me Me H H N 3-(trifluoromethyl)phenyl- amino 1-34 Me Me H H N 3-methoxyphenylamino 1-35 Me Me H H N 4-cyanophenylamino 1-36 Me Me H F N 4-fluorophenylamino 1-37 Me Me H F N 3,4-difluorophenylamino 1-38 Me Me H F N 3-(trifluoromethyl)phenyl- amino 1-39 Me Me H F N 3-methoxyphenylamino 1-40 Me Me H F N 4-cyanophenylamino 1-41 Me Me H Cl N 4-fluorophenylamino 1-42 Me Me H Cl N 3,4-difluorophenylamino 1-43 Me Me H Cl N 3-(trifluoromethyl)phenyl- amino 1-44 Me Me H Cl N 3-methoxyphenylamino 1-45 Me Me H Cl N 4-cyanophenylamino 1-46 Me Me COOEt H N 4-fluorophenylthio 1-47 Me Me COOEt F N 4-fluorophenylthio 1-48 Me Me COOEt Cl N 4-fluorophenylthio 1-49 COOMe COOMe H Cl N 4-fluorophenoxy 1-50 COOMe COOMe H Cl N 4-fluorophenylthio 1-51 CN CN H Cl N 4-fluorophenoxy 1-52 Me Me H H N phenoxy 1-53 Me Me H H N phenylthio 1-54 Me Me H H N phenylamino 1-55 Me Me H F N phenoxy 1-56 Me Me H F N phenylthio 1-57 Me Me H F N phenylamino 1-58 Me Me H Cl N phenoxy 1-59 Me Me H Cl N phenylthio 1-60 Me Me H Cl N phenylamino 1-61 Me Me H H N phenylmethyl 1-62 Me Me H H N 4-fluorophenylmethyl 1-63 Me Me H H N 3,4-difluorophenylmethyl 1-64 Me Me H H N 3-(trifluoromethyl)phenyl- methyl 1-65 Me Me H H N 3-methoxyphenylmethyl 1-66 Me Me H H N 4-cyanophenylmethyl 1-67 Me Me H F N phenylmethyl 1-68 Me Me H F N 4-fluorophenylmethyl 1-69 Me Me H F N 3,4-difluorophenylmethyl 1-70 Me Me H F N 3-(trifluoromethyl)phenyl- methyl 1-71 Me Me H F N 3-methoxyphenylmethyl 1-72 Me Me H F N 4-cyanophenylmethyl 1-73 Me Me H Cl N phenylmethyl 1-74 Me Me H Cl N 4-fluorophenylmethyl 1-75 Me Me H Cl N 3,4-difluorophenylmethyl 1-76 Me Me H Cl N 3-(trifluoromethyl)phenyl- methyl 1-77 Me Me H Cl N 3-methoxyphenylmethyl 1-78 Me Me H Cl N 4-cyanophenylmethyl 1-79 Me H H F N phenoxy 1-80 Me H H F N 4-fluorophenoxy 1-81 Me H H Cl N phenoxy 1-82 Me H H Cl N 4-fluorophenoxy 1-83 Me H H F N phenylthio 1-84 Me H H F N 4-fluorophenylthio 1-85 Me H H Cl N phenylthio 1-86 Me H H Cl N 4-fluorophenylthio 1-87 Me H H F N phenylmethyl 1-88 Me H H F N 4-fluorophenylmethyl 1-89 Me H H Cl N phenylmethyl 1-90 Me H H Cl N 4-fluorophenylmethyl 1-91 Me H H F N 5-fluoropyrimidin-2-yloxy 1-92 Me H H F N 5-chloropyrimidin-2-yloxy 1-93 Me H H Cl N 5-fluoropyrimidin-2-yloxy 1-94 Me H H Cl N 5-chloropyrimidin-2-yloxy 1-95 Me Me H Cl CH phenoxy 1-96 Me Me H Cl CH 4-fluorophenoxy 1-97 Me Me H Cl CH 3,4-difluorophenoxy 1-98 Me Me H Cl CH 3-methoxyphenoxy 1-99 Me Me H Cl CH 4-cyanophenoxy 1-100 Me Me H Cl CH phenylthio 1-101 Me Me H Cl CH 4-fluorophenylthio 1-102 Me Me H Cl CH 3,4-difluorophenylthio 1-103 Me Me H Cl CH 3-methoxyphenylthio 1-104 Me Me H Cl CH 4-cyanophenylthio 1-105 Me Me H Cl CH phenylamino 1-106 Me Me H Cl CH 4-fluorophenylamino 1-107 Me Me H Cl CH 3,4-difluorophenylamino 1-108 Me Me H Cl CH 3-methoxyphenylamino 1-109 Me Me H Cl CH 4-cyanophenylamino 1-110 Me Me H Cl CH phenylmethyl 1-111 Me Me H Cl CH 4-fluorophenylmethyl 1-112 Me Me H Cl CH 3,4-difluorophenylmethyl 1-113 Me Me H Cl CH 3-methoxyphenylmethyl 1-114 Me Me H Cl CH 4-cyanophenylmethyl

[0142] NMR data of the end products (manual evaluation)

TABLE-US-00002 Example number 1-26: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 8.40 (s, 2H); 7.08-7.05 (m, 2H); 6.94 (s, 1H); 6.90-6.86 (m, 2H); 2.65 (s, 3H); 2.58 (s, 3H) Example number 1-27: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 8.51 (s, 2H); 7.09-7.02 (m, 3H); 6.97-6.94 (m, 1H); 2.90 (s, 3H); 2.80 (s, 3H) Example number 1-28: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ = 8.68 (s, 2H); 7.53-7.45 (m, 2H); 7.33 (s, 1H); 7.28-7.25 (m, 3H); 2.56 (s, 3H); 2.29 (s, 3H) Example number 1-30: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ = 8.71 (s, 2H); 7.67 (ddd, 2H); 7.30 (s, 1H); 7.10 (ddd, 2H); 2.53 (s, 3H); 2.52 (s, 3H) Example number 1-31: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ = 11.49 (brs, 1H); 8.28 (d, 2H); 7.33 (m, 2H); 7.10 (m, 2H); 6.77 (t, 1H); 6.05 (s, 1H); 2.20 (s, 3H); 2.06 (s, 3H) Example number 1-32: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ = 11.28 (brs, 1H); 8.36 (d, 2H); 7.48 (m, 1H); 7.36 (m, 1H); 7.13 (m, 1H); 6.82 (t, 1H); 6.00 (s, 1H); 2.21 (s, 3H); 2.07 (s, 3H) Example number 1-34: .sup.1H-NMR (400.0 MHz, methanol-d.sub.4): δ = 8.32 (d, 2H); 7.24 (t, 1H); 6.98 (m, 1H); 6.90 (m, 1H); 6.81 (t, 1H); 6.75 (m, 1H); 6.32 (s, 1H); 3.74 (s, 3H); 2.34 (s, 3H); 2.17 (s, 3H) Example number 1-35: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ = 8.42 (d, 2H); 7.72 (d, 2H); 7.44 (d, 2H); 6.92 (t, 1H); 6.00 (s, 1H); 2.21 (s, 3H); 1.96 (s, 3H) Example number 1-36: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ = 8.38 (s, 2H); 7.34 (m, 2H); 7.11 (m, 2H); 5.98 (s, 1H); 2.18 (s, 3H); 2.05 (s, 3H) Example number 1-37: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ = 11.30 (brs, 1H); 8.45 (s, 2H); 7.46 (m, 1H); 7.34 (m, 1H); 7.11 (m, 1H); 6.00 (s, 1H); 2.21 (s, 3H); 2.07 (s, 3H) Example number 1-39: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ = 8.39 (s, 2H); 7.18 (t, 1H); 6.91 (m, 1H); 6.86 (m, 1H); 6.69 (m, 1H); 5.98 (s, 1H); 3.69 (s, 3H); 2.17 (s, 3H); 2.02 (s, 3H) Example number 1-40: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ = 8.52 (s, 2H); 7.72 (d, 2H); 7.41 (d, 2H); 6.02 (s, 1H); 2.23 (s, 3H); 1.98 (s, 3H) Example number 1-41: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ = 11.27 (brs, 1H); 8.39 (s, 2H); 7.37 (m, 2H); 7.13 (m, 2H); 5.99 (s, 1H); 2.20 (s, 3H); 2.07 (s, 3H) Example number 1-42: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ = 8.43 (s, 2H); 7.48 (m, 1H); 7.34 (m, 1H); 7.11 (m, 1H); 6.01 (s, 1H); 2.20 (s, 3H); 2.08 (s, 3H) Example number 1-44: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ = 11.24 (brs, 1H); 8.39 (s, 2H); 7.20 (t, 1H); 6.93 (m, 1H); 6.87 (m, 1H); 6.74 (m, 1H); 5.99 (s, 1H); 3.70 (s, 3H); 2.17 (s, 3H); 2.05 (s, 3H) Example number 1-45: .sup.1H-NMR (400.0 MHz, methanol-d.sub.4): δ = 8.43 (s, 2H); 7.69 (m, 2H); 7.56 (d, 2H); 6.36 (s, 1H); 2.41 (s, 3H); 2.16 (s, 3H) Example number 1-50: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ = 8.73 (s, 2H); 7.30 (m, 2H); 7.08 (m, 2H); 6.88 (s, 1H); 3.89 (s, 3H); 3.86 (s, 3H) Example number 1-86: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 8.57 (d, 1H); 8.41 (s, 2H); 7.12-7.06 (m, 3H); 6.91-6.87 (m, 2H); 2.68 (s, 3H) Example number 1-91: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 8.79 (d, 1H); 8.52 (s, 2H); 8.38 (s, 2H); 7.61 (d, 1H); 2.71 (s, 3H) Example number 1-106: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ = 11.36 (brs, 1H); 8.02 (d, 1H); 7.55 (m, 1H); 7.28 (m, 2H); 7.14 (m, 2H); 6.45 (m, 1H); 6.04 (s, 1H); 2.21 (s, 3H); 2.07 (s, 3H) Example number 1-107: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ = 11.40 (brs, 1H); 8.07 (s, 1H); 7.58 (m, 1H); 7.30-7.20 (m, 2H); 7.05 (m, 1H); 6.50 (m, 1H); 6.04 (s, 1H); 2.22 (s, 3H); 2.07 (s, 3H) Example number 1-108: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ = 11.28 (brs, 1H); 8.04 (s, 1H); 7.54 (m, 1H); 7.21 (m, 1H); 6.82-6.76 (m, 2H); 6.70 (m, 1H); 6.56 (m, 1H); 6.00 (s, 1H); 3.69 (s, 3H); 2.20 (s, 3H); 2.03 (s, 3H) Example number 1-109: .sup.1H-NMR (400.0 MHz, DMSO-d.sub.6): δ = 11.45 (brs, 1H); 8.02 (d, 1H); 7.69 (m, 1H); 7.66 (m, 2H); 7.23 (m, 2H); 6.74 (m, 1H); 6.05 (s, 1H); 2.24 (s, 3H); 1.98 (s, 3H)

[0143] The present invention further provides for the use of one or more compounds of the general formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I-001) to (I-114) and/or salts thereof, in each case as defined above, as herbicide and/or plant growth regulator, preferably in crops of useful plants and/or ornamentals.

[0144] The present invention further provides a method for controlling harmful plants and/or for regulating the growth of plants, characterized in that an effective amount [0145] of one or more compounds of the general formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I-001) to (I-114) and/or salts thereof, in each case as defined above, or [0146] of a composition according to the invention, as defined below, is applied to the (harmful) plants, seeds of (harmful) plants, the soil in which or on which the (harmful) plants grow or the area under cultivation.

[0147] The present invention also provides a method for controlling unwanted plants, preferably in crops of useful plants, characterized in that an effective amount [0148] of one or more compounds of the general formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I-001) to (I-114) and/or salts thereof, in each case as defined above, or [0149] of a composition according to the invention, as defined below, is applied to unwanted plants (for example harmful plants such as mono- or dicotyledonous weeds or unwanted crop plants), the seed of the unwanted plants (i.e. plant seeds, for example grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in which or on which the unwanted plants grow (for example the soil of crop land or non-crop land) or the area under cultivation (i.e. the area on which the unwanted plants will grow).

[0150] The present invention also further provides methods for controlling for regulating the growth of plants, preferably of useful plants, characterized in that an effective amount [0151] of one or more compounds of the general formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I-001) to (I-114) and/or salts thereof, in each case as defined above, or [0152] of a composition according to the invention, as defined below, [0153] is applied to the plant, the seed of the plant (i.e. plant seed, for example grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in which or on which the plants grow (for example the soil of crop land or non-crop land) or the area under cultivation (i.e. the area on which the plants will grow).

[0154] In this context, the compounds according to the invention or the compositions according to the invention can be applied for example by pre-sowing (if appropriate also by incorporation into the soil), pre-emergence and/or post-emergence processes. Specific examples of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention are as follows, though there is no intention to restrict the enumeration to particular species.

[0155] In a method according to the invention for controlling harmful plants or for regulating the growth of plants, one or more compounds of the general formula (I) and/or salts thereof are preferably employed for controlling harmful plants or for regulating growth in crops of useful plants or ornamental plants, where in a preferred embodiment the useful plants or ornamental plants are transgenic plants.

[0156] The compounds of the general formula (I) according to the invention and/or their salts are suitable for controlling the following genera of monocotyledonous and dicotyledonous harmful plants: Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

[0157] Dicotyledonous harmful plants of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

[0158] When the compounds of the general formula (I) according to the invention are applied to the soil surface before germination of the harmful plants (weed grasses and/or broad-leaved weeds) (pre-emergence method), either the seedlings of the weed grasses or broad-leaved weeds are prevented completely from emerging or they grow until they have reached the cotyledon stage, but then stop growing and eventually, after three to four weeks have elapsed, die completely.

[0159] If the active compounds of the general formula (I) are applied post-emergence to the green parts of the plants, growth stops after the treatment, and the harmful plants remain at the growth stage at the time of application, or they die completely after a certain time, so that in this manner competition by the weeds, which is harmful to the crop plants, is eliminated very early and in a sustained manner.

[0160] Although the compounds of the general formula (I) according to the invention display outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, are damaged only to an insignificant extent, or not at all, depending on the structure of the respective compound according to the invention and its application rate. For these reasons, the present compounds are very suitable for selective control of unwanted plant growth in plant crops such as agriculturally useful plants or ornamental plants.

[0161] In addition, the compounds of the general formula (I) according to the invention (depending on their particular structure and the application rate deployed) have outstanding growth-regulating properties in crop plants. They intervene in the plants' own metabolism with regulatory effect, and can thus be used for the controlled influencing of plant constituents and to facilitate harvesting, for example by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth without killing the plants in the process. Inhibition of vegetative growth plays a major role for many mono- and dicotyledonous crops since, for example, this can reduce or completely prevent lodging.

[0162] By virtue of their herbicidal and plant growth regulatory properties, the active compounds of the general formula (I) can also be used to control harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. In general, the transgenic plants are characterized by particular advantageous properties, for example by resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid composition in the harvested material.

[0163] It is preferred with a view to transgenic crops to use the compounds of the general formula (I) according to the invention and/or their salts in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, millet, rice and corn or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas and other vegetables.

[0164] It is preferable to employ the compounds of the general formula (I) according to the invention also as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

[0165] By virtue of their herbicidal and plant growth regulatory properties, the compounds of the general formula (I) according to the invention can also be used to control harmful plants in crops of genetically modified plants which are known or are yet to be developed. In general, the transgenic plants are characterized by particular advantageous properties, for example by resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid composition in the harvested material. Further special properties may be tolerance or resistance to abiotic stressors, for example heat, cold, drought, salinity and ultraviolet radiation.

[0166] Preference is given to the use of the compounds of the general formula (I) according to the invention or salts thereof in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and corn, or else crops of sugar beet, cotton, soybean, oilseed rape, potatoes, tomatoes, peas and other vegetables.

[0167] It is preferable to employ the compounds of the general formula (I) as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

[0168] Conventional ways of producing novel plants which have modified properties in comparison to existing plants consist, for example, in traditional cultivation methods and the generation of mutants. Alternatively, novel plants with altered properties can be generated with the aid of recombinant methods.

[0169] A large number of molecular-biological techniques by means of which novel transgenic plants with modified properties can be generated are known to the person skilled in the art. For such genetic manipulations, nucleic acid molecules which allow mutagenesis or sequence alteration by recombination of DNA sequences can be introduced into plasmids. With the aid of standard methods, it is possible, for example, to undertake base exchanges, remove part sequences or add natural or synthetic sequences. To connect the DNA fragments to each other, adapters or linkers may be added to the fragments.

[0170] For example, the generation of plant cells with a reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect, or by expressing at least one suitably constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product.

[0171] To this end, it is firstly possible to use DNA molecules which encompass the entire coding sequence of a gene product inclusive of any flanking sequences which may be present, and also DNA molecules which only encompass portions of the coding sequence, in which case it is necessary for these portions to be long enough to have an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical to them.

[0172] When expressing nucleic acid molecules in plants, the protein synthesized may be localized in any desired compartment of the plant cell. However, to achieve localization in a particular compartment, it is possible, for example, to join the coding region to DNA sequences which ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227). The nucleic acid molecules can also be expressed in the organelles of the plant cells.

[0173] The transgenic plant cells can be regenerated by known techniques to give rise to entire plants. In principle, the transgenic plants may be plants of any desired plant species, i.e. not only monocotyledonous but also dicotyledonous plants.

[0174] Thus, transgenic plants can be obtained whose properties are altered by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or expression of heterologous (=foreign) genes or gene sequences.

[0175] It is preferred to employ the compounds of the general formula (I) according to the invention in transgenic crops which are resistant to growth regulators such as, for example, dicamba, or to herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of the sulfonylureas, glyphosate, glufosinate or benzoylisoxazoles and analogous active compounds.

[0176] When the compounds of the general formula (I) according to the invention are employed in transgenic crops, not only do the effects toward harmful plants observed in other crops occur, but frequently also effects which are specific to application in the particular transgenic crop, for example an altered or specifically widened spectrum of weeds which can be controlled, altered application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing of growth and yield of the transgenic crop plants.

[0177] The invention therefore also relates to the use of the compounds of the general formula (I) according to the invention and/or their salts as herbicides for controlling harmful plants in crops of useful plants or ornamentals, optionally in transgenic crop plants.

[0178] Preference is given to the use of compounds of the general formula (I) in cereals, here preferably corn, wheat, barley, rye, oats, millet or rice, by the pre- or post-emergence method.

[0179] Preference is also given to the use of compounds of the general formula (I) in soybean by the pre-emergence or post-emergence method.

[0180] The use of inventive compounds of the formula (I) for the control of harmful plants or for growth regulation of plants also includes the case in which a compound of the general formula (I) or its salt is not formed from a precursor substance (“prodrug”) until after application on the plant, in the plant or in the soil.

[0181] The invention also provides the use of one or more compounds of the general formula (I) or salts thereof or of a composition according to the invention (as defined below) (in a method) for controlling harmful plants or for regulating the growth of plants which comprises applying an effective amount of one or more compounds of the general formula (I) or salts thereof onto the plants (harmful plants, if appropriate together with the useful plants), plant seeds, the soil in which or on which the plants grow or the area under cultivation.

[0182] The invention also provides a herbicidal and/or plant growth-regulating composition, characterized in that the composition comprises [0183] (a) one or more compounds of the general formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae [0184] (I-001) to (I-114) and/or salts thereof, in each case as defined above, and [0185] (b) one or more further substances selected from groups (i) and/or (ii): [0186] (i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (i.e. those not conforming to the general formula (I) defined above), fungicides, safeners, fertilizers and/or further growth regulators, [0187] (ii) one or more formulation auxiliaries customary in crop protection.

[0188] Here, the further agrochemically active substances of component (i) of a composition according to the invention are preferably selected from the group of substances mentioned in “The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.

[0189] A herbicidal or plant growth-regulating composition according to the invention comprises preferably one, two, three or more formulation auxiliaries (ii) customary in crop protection selected from the group consisting of surfactants, emulsifiers, dispersants, film-formers, thickeners, inorganic salts, dusting agents, carriers solid at 25° C. and 1013 mbar, preferably adsorptive granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoam agents, water, organic solvents, preferably organic solvents miscible with water in any ratio at 25° C. and 1013 mbar.

[0190] The compounds of the general formula (I) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in the customary formulations. The invention therefore also provides herbicidal and plant growth-regulating compositions which comprise compounds of the general formula (I) and/or salts thereof.

[0191] The compounds of the general formula (I) according to the invention and/or salts thereof can be formulated in various ways according to which biological and/or physicochemical parameters are specified. Possible formulations include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), dressings, granules for scattering and soil application, granules (GR) in the form of microgranules, spray granules, absorption and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

[0192] These individual formulation types and the formulation assistants, such as inert materials, surfactants, solvents and further additives, are known to the person skilled in the art and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J.; H. v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”, 2nd ed., Interscience, N.Y. 1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Athylenoxidaddukte” [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.

[0193] Wettable powders are preparations which can be dispersed uniformly in water and, in addition to the active compound, apart from a diluent or inert substance, also comprise surfactants of the ionic and/or nonionic type (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate. To produce the wettable powders, the herbicidally active compounds are finely ground, for example in customary apparatuses such as hammer mills, blower mills and air-jet mills, and simultaneously or subsequently mixed with the formulation auxiliaries.

[0194] Emulsifiable concentrates are produced by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents, with addition of one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are: calcium alkylarylsulfonate salts, for example calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.

[0195] Dusting products are obtained by grinding the active compound with finely distributed solids, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0196] Suspension concentrates may be water- or oil-based. They may be prepared, for example, by wet-grinding by means of commercial bead mills and optional addition of surfactants as have, for example, already been listed above for the other formulation types.

[0197] Emulsions, for example oil-in-water emulsions (EW), can be produced, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and optionally surfactants as already listed above, for example, for the other formulation types.

[0198] Granules can be prepared either by spraying the active compound onto granular inert material capable of adsorption or by applying active compound concentrates to the surface of carrier substances, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils. Suitable active compounds can also be granulated in the manner customary for the production of fertilizer granules—if desired as a mixture with fertilizers. Water-dispersible granules are produced generally by the customary processes such as spray-drying, fluidized-bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material.

[0199] For the production of pan, fluidized-bed, extruder and spray granules, see e.g. processes in “Spray-Drying Handbook” 3rd Ed. 1979, G. Goodwin Ltd., London; J. E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff; “Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw Hill, New York 1973, p. 8-57.

[0200] For further details regarding the formulation of crop protection compositions, see, for example, G. C. Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0201] The agrochemical preparations, preferably herbicidal or plant growth-regulating compositions, of the present invention preferably comprise a total amount of from 0.1 to 99% by weight, preferably 0.5 to 95% by weight, particularly preferably 1 to 90% by weight, especially preferably 2 to 80% by weight, of active compounds of the general formula (I) and their salts.

[0202] In wettable powders, the active compound concentration is, for example, about 10 to 90% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In emulsifiable concentrates, the active compound concentration may be about 1% to 90% and preferably 5% to 80% by weight. Formulations in the form of dusts comprise 1% to 30% by weight of active compound, preferably usually 5% to 20% by weight of active compound; sprayable solutions contain about 0.05% to 80% by weight, preferably 2% to 50% by weight of active compound. In the case of water-dispersible granules, the active compound content depends partially on whether the active compound is in liquid or solid form and on which granulation auxiliaries, fillers, etc., are used. In the water-dispersible granules, the content of active compound is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

[0203] In addition, the active compound formulations mentioned optionally comprise the respective customary stickers, wetters, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH and the viscosity. Examples of formulation auxiliaries are described inter alia in “Chemistry and Technology of Agrochemical Formulations”, ed. D. A. Knowles, Kluwer Academic Publishers (1998).

[0204] The compounds of the general formula (I) according to the invention or salts thereof can be used as such or in the form of their preparations (formulations) in a combination with other pesticidally active substances, for example insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or of a tank mix. The combination formulations can be prepared on the basis of the abovementioned formulations, while taking account of the physical properties and stabilities of the active compounds to be combined.

[0205] Active compounds which can be employed in combination with the compounds of the general formula (I) according to the invention in mixture formulations or in a tank mix are, for example, known active compounds based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and literature cited therein.

[0206] Of particular interest is the selective control of harmful plants in crops of useful plants and ornamentals. Although the compounds of the general formula (I) according to the invention have already demonstrated very good to adequate selectivity in a large number of crops, in principle, in some crops and in particular also in the case of mixtures with other, less selective herbicides, phytotoxicities on the crop plants may occur. In this connection, combinations of compounds of the general formula (I) according to the invention that are of particular interest are those which comprise the compounds of the general formula (I) or their combinations with other herbicides or pesticides and safeners. The safeners, which are used in an antidotically effective amount, reduce the phytotoxic side effects of the herbicides/pesticides employed, for example in economically important crops, such as cereals (wheat, barley, rye, corn, rice, millet), sugarbeet, sugarcane, oilseed rape, cotton and soybeans, preferably cereals.

[0207] The weight ratios of herbicide (mixture) to safener depend generally on the herbicide application rate and the efficacy of the safener in question and may vary within wide limits, for example in the range from 200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1 to 1:20. Analogously to the compounds of the general formula (I) or mixtures thereof, the safeners can be formulated with further herbicides/pesticides and be provided and employed as a finished formulation or tank mix with the herbicides.

[0208] For application, the herbicide or herbicide/safener formulations present in commercial form are, if appropriate, diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules with water. Dust-type preparations, granules for soil application or granules for scattering and sprayable solutions are not normally diluted further with other inert substances prior to application.

[0209] The application rate of the compounds of the general formula (I) and/or their salts is affected to a certain extent by external conditions such as temperature, humidity, etc. Here, the application rate may vary within wide limits. For the application as a herbicide for controlling harmful plants, the total amount of compounds of the general formula (I) and their salts is preferably in the range from 0.001 to 10.0 kg/ha, with preference in the range from 0.005 to 5 kg/ha, more preferably in the range from 0.01 to 1.5 kg/ha, particularly preferably in the range from 0.05 to 1 kg/ha. This applies both to the pre-emergence and the post-emergence application.

[0210] When the compounds of the general formula (I) according to the invention and/or their salts are used as plant growth regulator, for example as culm stabilizer for crop plants like those mentioned above, preferably cereal plants, such as wheat, barley, rye, triticale, millet, rice or corn, the total application rate is preferably in the range of from 0.001 to 2 kg/ha, preferably in the range of from 0.005 to 1 kg/ha, in particular in the range of from 10 to 500 g/ha, very particularly preferably in the range from 20 to 250 g/ha. This applies both to the pre-emergence and the post-emergence application.

[0211] The application as culm stabilizer may take place at various stages of the growth of the plants. Preferred is, for example, the application after the tittering phase, at the beginning of the longitudinal growth.

[0212] As an alternative, application as plant growth regulator is also possible by treating the seed, which includes various techniques for dressing and coating seed. Here, the application rate depends on the particular techniques and can be determined in preliminary tests.

[0213] Active compounds which can be employed in combination with the compounds of the general formula (I) according to the invention in compositions according to the invention (for example in mixed formulations or in the tank mix) are, for example, known active compounds which are based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase, as are described in, for example, Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein. Known herbicides or plant growth regulators which can be combined with the compounds of the invention are, for example, the following, where said active compounds are designated either with their “common name” in accordance with the International Organization for Standardization (ISO) or with the chemical name or with the code number. They always encompass all the use forms, such as, for example, acids, salts, esters and also all isomeric forms such as stereoisomers and optical isomers, even if they are not mentioned explicitly.

[0214] Examples of such herbicidal mixing partners are:

acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate and -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, -dimethylammonium, -diolamine, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide, F-7967, i.e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium and -trimesium, H-9201, i.e. 0-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropylphosphoramidothioate, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl (2,4-dichlorophenoxy)acetate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYN-523, SYP-249, i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e. 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, and the following compounds:

##STR00012##

[0215] Examples of plant growth regulators as possible mixing partners are:

acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechol, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, -disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid methyl ester, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazole, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

[0216] Useful combination partners for the compounds of the general formula (I) according to the invention also include, for example, the following safeners: [0217] S1) Compounds from the group of heterocyclic carboxylic acid derivatives: [0218] S1.sup.a) Compounds of the dichlorophenylpyrazoline-3-carboxylic acid type (S1.sup.a), preferably compounds such as 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (S1-1) (“mefenpyr-diethyl”), and related compounds as described in WO-A-91/07874; [0219] S1.sup.b) Derivatives of dichlorophenylpyrazolecarboxylic acid (S1.sup.b), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (S1-4) and related compounds as described in EP-A-333131 and EP-A-269806; [0220] S1.sup.c) Derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1.sup.c), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6) and related compounds as described, for example, in EP-A-268554; [0221] S1.sup.d) Compounds of the triazolecarboxylic acid type (S1.sup.d), preferably compounds such as fenchlorazole(-ethyl ester), i.e. ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (S1-7), and related compounds, as described in EP-A-174562 and EP-A-346620; [0222] S1.sup.e) Compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or of the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid type (SP), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related compounds as described in WO-A-91/08202, or 5,5-diphenyl-2-isoxazolinecarboxylic acid (S1-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-11) (“isoxadifen-ethyl”) or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13) as described in patent application WO-A-95/07897. [0223] S2) Compounds from the group of the 8-quinolinoxy derivatives (S2): [0224] S2a) Compounds of the 8-quinolinoxyacetic acid type (S2a), preferably 1-methylhexyl (5-chloro-8-quinolinoxy)acetate (“cloquintocet-mexyl”) (S2-1), 1,3-dimethylbut-1-yl (5-chloro-8-quinolinoxy)acetate (S2-2), 4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate (S2-3), 1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate (S2-4), ethyl (5-chloro-8-quinolinoxy)acetate (S2-5),
methyl (5-chloro-8-quinolinoxy)acetate (S2-6),
allyl (5-chloro-8-quinolinoxy)acetate (S2-7), 2-(2-propylideneiminoxy)-1-ethyl (5-chloro-8-quinolinoxy)acetate (S2-8), 2-oxoprop-1-yl (5-chloro-8-quinolinoxy)acetate (S2-9) and related compounds, as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0 492 366, and also (5-chloro-8-quinolinoxy)acetic acid (S2-10), hydrates and salts thereof, for example the lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts thereof, as described in WO-A-2002/34048; [0225] S2.sup.b) Compounds of the (5-chloro-8-quinolinoxy)malonic acid type (S2.sup.b), preferably compounds such as diethyl (5-chloro-8-quinolinoxy)malonate, diallyl (5-chloro-8-quinolinoxy)malonate, methyl ethyl (5-chloro-8-quinolinoxy)malonate and related compounds, as described in EP-A-0 582 198. [0226] S3) Active compounds of the dichloroacetamide type (S3), which are frequently used as pre-emergence safeners (soil-acting safeners), for example
“dichlormid” (N,N-diallyl-2,2-dichloroacetamide) (S3-1),
“R-29148” (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2),
“R-28725” (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) from Stauffer (S3-3),
“benoxacor” (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),
“PPG-1292” (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) from PPG Industries (S3-5),
“DKA-24” (N-allyl-N-Rallylaminocarbonyl)methylldichloroacetamide) from Sagro-Chem (S3-6),
“AD-67” or “MON 4660” (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) from Nitrokemia or Monsanto (S3-7),
“TI-35” (1-dichloroacetylazepane) from TRI-Chemical RT (S3-8),
“diclonon” (dicyclonon) or “BAS145138” or “LAB145138” (S3-9)
((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) from BASF,
“furilazole” or “MON 13900” ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (53-10), and the (R) isomer thereof (S3-11). [0227] S4) Compounds from the class of the acylsulfonamides (S4): [0228] S4.sup.a) N-Acylsulfonamides of the formula (S4.sup.a) and salts thereof, as described in WO-A-97/45016,

##STR00013## [0229] in which [0230] R.sub.A.sup.1 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, where the 2 latter radicals are substituted by v.sub.A substituents from the group of halogen, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy and (C.sub.1-C.sub.4)-alkylthio and, in the case of cyclic radicals, also by (C.sub.1-C.sub.4)-alkyl and (C.sub.1-C.sub.4)-haloalkyl; [0231] R.sub.A.sup.2 represents halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, CF.sub.3; [0232] m.sub.A represents 1 or 2; [0233] v.sub.A represents 0, 1, 2 or 3; [0234] S4.sup.b) Compounds of the 4-(benzoylsulfamoyl)benzamide type of the formula (S4.sup.b) and salts thereof, as described in WO-A-99/16744,

##STR00014## [0235] in which [0236] R.sub.B.sup.1, R.sub.B.sup.2 independently of one another represent hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-alkenyl, (C.sub.3-C.sub.6)-alkynyl, [0237] R.sub.B.sup.3 represents halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl or (C.sub.1-C.sub.4)-alkoxy and [0238] m.sub.b represents 1 or 2, [0239] e.g. those in which [0240] R.sub.B.sup.1=cyclopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=2-OMe (“cyprosulfamide”, S4-1), [0241] R.sub.B.sup.1=cyclopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=5-Cl-2-OMe (S4-2), [0242] R.sub.B.sup.1=ethyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=2-OMe (S4-3), [0243] R.sub.B.sup.1=isopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=5-Cl-2-OMe (S4-4) and [0244] R.sub.B.sup.1=isopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=2-OMe (S4-5); [0245] S4.sup.c) Compounds from the class of the benzoylsulfamoylphenylureas of the formula (S4c), as described in EP-A-365484,

##STR00015## [0246] in which [0247] R.sub.C.sup.1, R.sub.C.sup.2 independently of one another represent hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.6)-alkenyl, (C.sub.3-C.sub.6)-alkynyl, [0248] R.sub.C.sup.3 represents halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, CF.sub.3 and [0249] m.sub.C represents 1 or 2; [0250] for example [0251] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, [0252] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, [0253] 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea; [0254] S4.sup.d) Compounds of the N-phenylsulfonylterephthalamide type of the formula (S4.sup.d) and salts thereof, which are known, for example, from CN 101838227,

##STR00016## [0255] in which [0256] R.sub.D.sup.4 represents halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, CF.sub.3; [0257] m.sub.D represents 1 or 2; [0258] R.sub.D.sup.5 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.5-C.sub.6)-cycloalkenyl. [0259] S5) Active compounds from the class of the hydroxyaromatics and the aromatic-aliphatic carboxylic acid derivatives (S5), for example [0260] ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001. [0261] S6) Active compounds from the class of the 1,2-dihydroquinoxalin-2-ones (S6), for example [0262] 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, as described in WO-A-2005/112630. [0263] S7) Compounds from the class of the diphenylmethoxyacetic acid derivatives (S7), e.g. methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1), ethyl diphenylmethoxyacetate or diphenylmethoxyacetic acid, as described in WO-A-98/38856. [0264] S8) Compounds of the formula (S8), as described in WO-A-98/27049,

##STR00017## [0265] in which the symbols and indices are defined as follows: [0266] R.sub.D.sup.1 represents halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, [0267] R.sub.D.sup.2 represents hydrogen or (C.sub.1-C.sub.4)-alkyl, [0268] R.sub.D.sup.3 represents hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-alkynyl or aryl, where each of the aforementioned carbon-containing radicals is unsubstituted or substituted by one or more, preferably up to three, identical or different radicals from the group consisting of halogen and alkoxy; or salts thereof, [0269] n.sub.D represents an integer from 0 to 2. [0270] S9) Active compounds from the class of the 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), for example 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No.: 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999/000020. [0271] S10) Compounds of the formula (S10a) or (S10.sup.b) [0272] as described in WO-A-2007/023719 and WO-A-2007/023764 [0273] in which

##STR00018## [0274] R.sub.E.sup.1 represents halogen, (C.sub.1-C.sub.4)-alkyl, methoxy, nitro, cyano, CF.sub.3, OCF.sub.3, [0275] Y.sub.E, Z.sub.E independently of one another represent O or S, [0276] n.sub.E represents an integer from 0 to 4, [0277] R.sub.E.sup.2 represents (C.sub.1-C.sub.16)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.3-C.sub.6)-cycloalkyl, aryl; benzyl, halobenzyl, [0278] R.sub.E.sup.3 represents hydrogen or (C.sub.1-C.sub.6)-alkyl. [0279] S11) Active compounds of the oxyimino compounds type (S11), which are known as seed-dressing agents, for example [0280] “oxabetrinil” ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage, “fluxofenim” (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone 0-(1,3-dioxolan-2-ylmethyl)oxime) (S11-2), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage, and [0281] “cyometrinil” or “CGA-43089” ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage. [0282] S12) Active compounds from the class of the isothiochromanones (S12), for example methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998/13361. [0283] S13) One or more compounds from group (S13): [0284] “naphthalic anhydride” (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed-dressing safener for corn against thiocarbamate herbicide damage, [0285] “fenclorim” (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice, [0286] “flurazole” (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is known as a seed-dressing safener for millet/sorghum against alachlor and metolachlor damage, “CL 304415” (CAS Reg. No. 31541-57-8) [0287] (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a safener for corn against damage by imidazolinones, [0288] “MG 191” (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for corn, [0289] “MG 838” (CAS Reg. No. 133993-74-5) [0290] (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from Nitrokemia [0291] “disulfoton” (0,0-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7), [0292] “dietholate” (0,0-diethyl 0-phenyl phosphorothioate) (S13-8), [0293] “mephenate” (4-chlorophenyl methylcarbamate) (S13-9). [0294] S14) Active compounds which, in addition to herbicidal action against harmful plants, also have safener action on crop plants such as rice, for example [0295] “dimepiperate” or “MY-93” (S-1-methyl 1-phenylethylpiperidine-1-carbothioate), which is known as a safener for rice against damage by the herbicide molinate, [0296] “daimuron” or “SK 23” (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as a safener for rice against damage by the herbicide imazosulfuron, [0297] “cumyluron”=“JC-940” (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60087270), which is known as a safener for rice against damage by some herbicides, [0298] “methoxyphenone” or “NK 049” (3,3′-dimethyl-4-methoxybenzophenone), which is known as a safener for rice against damage by some herbicides, [0299] “CSB” (1-bromo-4-(chloromethylsulfonyl)benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage by some herbicides in rice. [0300] S15) Compounds of the formula (S15) or tautomers thereof

##STR00019## [0301] as described in WO-A-2008/131,861 and WO-A-2008/131,860 [0302] in which [0303] R.sub.H.sup.1 represents a (C.sub.1-C.sub.6)-haloalkyl radical and [0304] R.sub.H.sup.2 represents hydrogen or halogen and [0305] R.sub.H.sup.3, R.sub.H.sup.4 independently of one another represent hydrogen, (C.sub.1-C.sub.16)-alkyl, (C.sub.2-C.sub.16)-alkenyl or (C.sub.2-C.sub.16)-alkynyl, [0306] where each of the 3 latter radicals is unsubstituted or substituted by one or more radicals from the group of halogen, hydroxyl, cyano, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-alkylamino, di[(C.sub.1-C.sub.4)-alkyl]amino, [(C.sub.1-C.sub.4)-alkoxy]carbonyl, [(C.sub.1-C.sub.4)-haloalkoxy]carbonyl, (C.sub.3-C.sub.6)-cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, [0307] or (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.4-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl fused on one side of the ring to a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C.sub.4-C.sub.6)-cycloalkenyl fused on one side of the ring to a 4 to 6-membered saturated or unsaturated carbocyclic ring, [0308] where each of the 4 latter radicals is unsubstituted or substituted by one or more radicals from the group of halogen, hydroxyl, cyano, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-alkylamino, di[(C.sub.1-C.sub.4)-alkyl]amino, RC.sub.1-C.sub.4)-alkoxylcarbonyl, RC.sub.1-C.sub.4)-haloalkoxylcarbonyl, (C.sub.3-C.sub.6)-cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, [0309] or [0310] R.sub.H.sup.3 represents (C.sub.1-C.sub.4)-alkoxy, (C.sub.2-C.sub.4)-alkenyloxy, (C.sub.2-C.sub.6)-alkynyloxy or (C.sub.2-C.sub.4)-haloalkoxy and [0311] R.sub.H.sup.4 represents hydrogen or (C.sub.1-C.sub.4)-alkyl or [0312] R.sub.H.sup.3 and R.sub.H.sup.4 together with the directly attached nitrogen atom represent a four- to eight-membered heterocyclic ring which, as well as the nitrogen atom, may also contain further ring heteroatoms, preferably up to two further ring heteroatoms from the group of N, O and S, and which is unsubstituted or substituted by one or more radicals from the group of halogen, cyano, nitro, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy and (C.sub.1-C.sub.4)-alkylthio. [0313] S16) Active compounds which are used primarily as herbicides but also have safener action on crop plants, for example [0314] (2,4-dichlorophenoxy)acetic acid (2,4-D), [0315] (4-chlorophenoxy)acetic acid, [0316] (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), [0317] 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), [0318] (4-chloro-o-tolyloxy)acetic acid (MCPA), [0319] 4-(4-chloro-o-tolyloxy)butyric acid, [0320] 4-(4-chlorophenoxy)butyric acid, [0321] 3,6-dichloro-2-methoxybenzoic acid (dicamba),

[0322] 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor-ethyl). Preferred safeners in combination with the compounds of the general formula (I) according to the invention and/or salts thereof, in particular with the compounds of the formulae (I-1) to (1-229) and/or salts thereof, are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole ethyl ester, isoxadifen-ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.

BIOLOGICAL EXAMPLES

[0323] A. Herbicidal Early Post-Emergence Action

[0324] Seeds of monocotyledonous or dicotyledonous weed plants were placed in 96-well microtiter plates in quartz sand and grown in a climatized chamber under controlled growth conditions. 5 to 7 days after sowing, the test plants were treated at the cotyledon stage. The compounds according to the invention, formulated in the form of emulsion concentrates (EC), were applied with a water application rate of the equivalent of 2200 liters per hectare. After the test plants had been left to stand in the climatized chamber for 9 to 12 days under optimum growth conditions, the effect of the preparations was scored visually in comparison to untreated controls. For example, 100% activity=the plants have died, 0% activity=like control plants.

[0325] Tables A1 to A6 below show the effects of selected compounds of the general formula (I) according to Table 1 on various harmful plants and an application rate corresponding to 1900 g/ha, which were obtained by the experimental procedure mentioned above.

TABLE-US-00003 TABLE A1 Early post-emergence action against Agrostis tenuis (AGSTE) Example Dosage number [g/ha] AGSTE 1-50 1900  80 1-86 1900 100

TABLE-US-00004 TABLE A2 Early post-emergence action against Poa annua (POAAN) Example Dosage number [g/ha] POAAN 1-86 1900 100

TABLE-US-00005 TABLE A3 Early post-emergence action against Lolium perenne (LOLPE) Example Dosage number [g/ha] LOLPE 1-86 1900 80

TABLE-US-00006 TABLE A4 Early post-emergence action against Setaria viridis (SETVI) Example Dosage number [g/ha] SETVI 1-86 1900 80

TABLE-US-00007 TABLE A5 Early post-emergence action against Diplotaxis muralis (DIPTE) Example Dosage number [g/ha] DIPTE 1-86 1900 80

TABLE-US-00008 TABLE A6 Early post-emergence action against Veronica persica (VERPE) Example Dosage number [g/ha] VERPE 1-86 1900 80

[0326] The test results show that compounds of the general formula (I) according to the invention, in the case of early post-emergence treatment, have good herbicidal activity against selected harmful plants such as Agrostis tenuis (AGOSTE), Poa annua (POAAN), Lolium perenne (LOLPE), Setaria viridis (SETVI), Diplotaxis muralis (DIPTE) and Veronica persica (VERPE) at an application rate of 1900 g of active substance per hectare.

[0327] B. Herbicidal Post-Emergence Action

[0328] Seeds of mono- and dicotyledonous weed plants were placed in plastic pots in sandy loam soil (doubly sown with in each case one species of mono- or dicotyledonous weed plants per pot), covered with soil and cultivated in a greenhouse under controlled growth conditions. 2 to 3 weeks after sowing, the test plants were treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were applied onto the green parts of the plants as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate of 600 liters per hectare (converted). After the test plants had been kept in the greenhouse under optimum growth conditions for about 3 weeks, the activity of the preparations was rated visually in comparison to untreated controls. For example, 100% activity=the plants have died, 0% activity=like control plants. Tables B1 to B6 below show the effects of selected compounds of the general formula (I) according to Table 1 on various harmful plants and an application rate corresponding to 1280 g/ha, which were obtained by the experimental procedure mentioned above.

TABLE-US-00009 TABLE B1 Post-emergence action against Echinochloa crus-galli (ECHCG) Example Dosage number [g/ha] ECHCG 1-26 1280 100 1-27 1280 100 1-30 1280 100

TABLE-US-00010 TABLE B2 Post-emergence action against Poa annua (POAAN) Example Dosage number [g/ha] POAAN 1-26 1280 100 1-28 1280 100 1-30 1280 100

TABLE-US-00011 TABLE B3 Post-emergence action against Setaria viridis (SETVI) Example Dosage number [g/ha] SETVI 1-26 1280 90

TABLE-US-00012 TABLE B4 Post-emergence action against Abutilon theophrasti (ABUTH) Example Dosage number [g/ha] ABUTH 1-26 1280 100 1-27 1280  90

TABLE-US-00013 TABLE B5 Post-emergence action against Amaranthus retroflexus (AMARE) Example Dosage number [g/ha] AMARE 1-26 1280 100 1-27 1280 100 1-28 1280  90

TABLE-US-00014 TABLE B6 Post-emergence action against Stellaria media (STEME) Example Dosage number [g/ha] STEME 1-26 1280 100 1-27 1280 100 1-28 1280 100 1-30 1280 100

[0329] The test results show that compounds of the general formula (I) according to the invention, in the case of post-emergence treatment, have good herbicidal activity against selected harmful plants such as Echinochloa crus-galli (ECHCG), Setaria viridis (SETVI), Poa annua (POAAN), Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE) and Stellaria media (STEME) at an application rate of 1280 g of active substance per hectare.

[0330] C. Herbicidal Pre-Emergence Action

[0331] Seeds of mono- and dicotyledonous weed plants were placed in plastic pots in sandy loam soil (doubly sown with in each case one species of mono- or dicotyledonous weed plants per pot) and covered with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were then applied onto the surface of the covering soil as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate of 600 liters per hectare (converted). After the treatment, the pots were placed in a greenhouse and kept under good growth conditions for the test plants. After about 3 weeks, the effect of the preparations was scored visually in comparison with untreated controls as percentages. For example, 100% activity=the plants have died, 0% activity=like control plants.

[0332] Tables C1 to C8 below show the effects of selected compounds of the general formula (I) according to Table 1 on various harmful plants and an application rate corresponding to 1280 g/ha, which were obtained by the experimental procedure mentioned above.

TABLE-US-00015 TABLE C1 Pre-emergence action against Echinochloa crus-galli (ECHCG) Example Dosage number [g/ha] ECHCG 1-26 1280 100 1-27 1280 100 1-30 1280 100

TABLE-US-00016 TABLE C2 Pre-emergence action against Lolium rigidum (LOLRI) Example Dosage number [g/ha] LOLRI 1-26 1280 100 1-27 1280 100 1-30 1280  90

TABLE-US-00017 TABLE C3 Pre-emergence action against Poa annua (POAAN) Example Dosage number [g/ha] POAAN 1-26 1280 100 1-27 1280 100 1-28 1280  90 1-30 1280 100

TABLE-US-00018 TABLE C4 Pre-emergence action against Setaria viridis (SETVI) Example Dosage number [g/ha] SETVI 1-26 1280 100 1-27 1280 100 1-30 1280  90

TABLE-US-00019 TABLE C5 Pre-emergence action against Abutilon theophrasti (ABUTH) Example Dosage number [g/ha] ABUTH 1-26 1280 100 1-27 1280 90 1-30 1280 90

TABLE-US-00020 TABLE C6 Pre-emergence action against Amaranthus retroflexus (AMARE) Example Dosage number [g/ha] AMARE 1-26 1280 100 1-27 1280 100 1-28 1280  90 1-30 1280 100 1-91 1280 100

TABLE-US-00021 TABLE C7 Pre-emergence action against Matricaria inodora (MATIN) Example Dosage number [g/ha] MATIN 1-26 1280 100 1-27 1280 100 1-28 1280 90 1-30 1280 90 1-91 1280 90

TABLE-US-00022 TABLE C8 Pre-emergence action against Stellaria media (STEME) Example Dosage number [g/ha] STEME 1-26 1280 100 1-27 1280 100 1-28 1280 100 1-30 1280 100 1-91 1280  90

[0333] The test results show that compounds of the general formula (I) according to the invention, in the case of pre-emergence treatment, have good herbicidal activity against selected harmful plants such as Echinochloa crus-galli (ECHCG), Lolium rigidum (LOLRI), Setaria viridis (SETVI), Poa annua (POAAN), Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE), Stellaria media (STEME) and Matricaria inodora (MATIN) at an application rate of 1280 g of active substance per hectare.