EP0968195A1

EP0968195A1 - Arylalkyltriazole derivatives and their use as herbicides

Info

Publication number: EP0968195A1
Application number: EP98906866A
Authority: EP
Inventors: Roland Andree; Mark Wilhelm Drewes; Andreas Lender; Karl-Heinz Linker; Otto Schallner; Markus Dollinger
Original assignee: Bayer AG
Current assignee: Bayer AG
Priority date: 1997-01-24
Filing date: 1998-01-10
Publication date: 2000-01-05
Also published as: AU723070B2; CN1244195A; KR20000069840A; AU6292398A; CA2278673A1; DE19702435A1; US6200935B1; JP2001509794A; BR9807509A; WO1998032745A1

Abstract

The invention concerns novel arylalkyl compounds of general formula (I) in which Q stands for O, S, SO or SO2, R1 stands for hydrogen or optionally substituted alkyl, R2 stands for hydrogen or optionally substituted alkyl, Z stands for one of the groups: (a), (b), (c), and (Y)¿n?, (X)m, R?3, R4, R5, R6, R7 and R8¿ stand for hydrogen or given substituents. The invention also concerns processes for preparing these compounds, novel intermediate products, and the use of the arylalkyl compounds as herbicides.

Description

ARYLAL YLTRIAZOLE DERIVATIVES AND THEIR USE AS HERBIC IZIDES

The invention relates to new arylalkyl compounds, processes for their preparation, new intermediates and their use as herbicides.

Some arylalkyl compounds are already known from the (patent) literature as potential herbicides (cf. DE 2526358, US 4249934, US 5262390, WO 9621647). However, these connections have not gained any significant practical importance.

New arylalkyl compounds of the general formula (I) have now been found

in which

m represents the numbers 0 to 5,

n stands for the numbers 0 to 4,

Q represents O, S, SO or SO ₂ ,

R ^{1 represents} hydrogen or optionally substituted alkyl,

R ^{2 represents} hydrogen or optionally substituted alkyl,

X for hydroxy, mercapto, amino, hydroxya ino, nitro, formyl, carboxy,

Cyano, carbamoyl, thiocarbamoyl, halogen, or for a radical of the series which is optionally substituted by cyano, halogen or alkoxy

Alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl or alkoxycarbonyl, Y represents nitro, carboxy, cyano, carbamoyl, thiocarbamoyl, halogen, or a radical of the series alkyl, alkoxy, alkylthio, alkylsulfmyl or alkylsulfonyl which is optionally substituted by cyano, halogen or alkoxy, and

Z represents one of the groupings below

wherein

R ^{3 represents} hydrogen, cyano, formyl, or a radical of the series which is optionally substituted by cyano, halogen or alkoxy

Is alkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl or alkynyl,

R ^{4 represents} hydrogen, cyano, formyl, or a radical of the series alkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl or alkynyl which is optionally substituted by cyano, halogen or alkoxy,

R ^{5 represents} hydrogen, cyano, formyl, or a radical of the series alkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl or alkynyl which is optionally substituted by cyano, halogen or alkoxy,

R ^{6 represents} hydrogen, cyano, formyl, or a radical of the series alkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl or alkynyl which is optionally substituted by cyano, halogen or alkoxy,

R ^{7 represents} hydrogen, amino, cyano, formyl, or a radical of the series alkyl, alkoxy, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkenyl, alkynyl or cycloalkyl which is optionally substituted by cyano, halogen or alkoxy, and

R ⁸ for hydrogen, halogen, or for each optionally by

Cyano, halogen or alkoxy substituted radical of the series alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylamino, dialkyl amino, alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkynyl, alkynyloxy, alkynylthio, cycloalkyl, cycloalkyloxy, cycloalkylthio or cycloalkylamino, or together with R ^{7 stands} for alkanediyl (alkylene).

The new arylalkyl compounds of the general formula (I) are obtained if

(a) 4-aryl-semicarbazides of the general formula (II)

in which

m, n, Q, R ¹ , R ² , R ³ , R ⁴ , X and Y have the meanings given above and

R represents alkyl,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, condensed cyclizing and, if appropriate, subsequently carrying out electrophilic or nucleophilic substitution reactions as part of the definition of substituents,

or if you

(b) 1-aryl-semicarbazides of the general formula (III)

in which

m, n, Q, R ¹ , R ² , R ⁵ , R ⁶ , X and Y have the meanings given above,

with phosgene, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and if appropriate subsequently carrying out electrophilic or nucleophilic substitution reactions in the course of the definition of the substituent,

or if you

(c) haloarenes of the general formula (IV)

in which

m, n, Q, R ¹ , R ² , X and Y have the meanings given above and

X ^{1 represents} halogen,

with heterocyclic compounds of the general formula (V)

ZH (V) in which

Z has the meaning given above,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent and if appropriate subsequently carrying out electrophilic or nucleophilic substitution reactions as part of the substituent definition,

or if you

(d) arylalkyl halides of the general formula (VI)

in which

m, R ¹ , R ² and X have the meanings given above and

X ^{2 represents} halogen,

with arenes of the general formula (VII)

in which

n, Y and Z have the meanings given above and

Q ^{1 represents} oxygen or sulfur, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and if appropriate subsequently then carries out electrophilic or nucleophilic substitution reactions in the usual manner as part of the definition of substituents

The compounds of the general formula (I) can also be converted into other compounds of the general formula (I) according to the above by further customary methods

Definition can be converted, for example by conventional conversions of carboxylic acid groups or their derivatives (e.g. X: COOH -> COOCH3, COOCH3 → CONH ₂ , CONH ₂ → CN, CN → CSNH ₂ ), by alkylation reactions (e.g. R ³ , R ⁴ , R ⁵ , R ⁶ 'H → CH3 or CHF2) or by oxidation (eg BQS - »SO or SO ₂ ) - see also the manufacturing examples.

The new substituted arylalkyl compounds of the general formula (I) are notable for strong herbicidal activity

In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkynyl, are each straight-chain or branched.

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably

Fluorine, chlorine or bromine, especially for fluorine or chlorine.

The invention preferably relates to compounds of the formula (I) in which

m represents the numbers 0 to 4,

n represents the numbers 0 to 3,

Q represents O, S, SO or SO ₂ ,

R ^{1 represents} hydrogen or alkyl which has 1 to 6 carbon atoms and is optionally substituted by halogen,

R ^{2 represents} hydrogen or alkyl which has 1 to 6 carbon atoms and is optionally substituted by halogen,

X for hydroxy, mercapto, amino, hydroxyamino, nitro, formyl, carboxy, cyano, carbamoyl, thiocarbamoyl, halogen, or for a radical of the series alkyl, alkoxy, alkylthio which is optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy , Alkylsulfmyl, alkylsulfonyl, alkylamino, di alkylamino, alkylcarbonyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups,

Y for nitro, carboxy, cyano, carbamoyl, thiocarbamoyl, halogen, or for a radical of the series alkyl, alkoxy, alkylthio, alkylsulfmyl or alkylsulfonyl each having 1 to 6 carbon atoms each optionally substituted by cyano, halogen or C -C-alkoxy is in the alkyl groups, and

Z represents one of the groupings below

R * O R »

o o o

wherein

R ^{3 represents} hydrogen, cyano, formyl, or a radical of the series alkyl, alkylcarbonyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C1-C4alkoxy, each having 1 to 6 carbon atoms in the alkyl groups, or each optionally substituted by halogen Is alkenyl or alkynyl each having 2 to 6 carbon atoms,

R ⁴ for hydrogen, cyano, formyl, or for a radical which is optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy

Series of alkyl, alkylcarbonyl or alkoxycarbonyl each with 1 to 6

Carbon atoms in the alkyl groups, or for each optionally substituted by halogen alkenyl or alkynyl each with 2 to

6 carbon atoms,

R ⁵ for hydrogen, cyano, formyl, or for a radical of the series alkyl, alkylcarbonyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, each having 1 to 6 carbon atoms in the alkyl groups, or for each optionally substituted by halogen Is alkenyl or alkynyl each having 2 to 6 carbon atoms, R ⁶ for hydrogen, cyano, formyl, or for a radical optionally substituted by cyano, halogen or C1-C4-alkoxy

Series of alkyl, alkylcarbonyl or alkoxycarbonyl each with 1 to 6

6 carbon atoms,

R ⁷ for hydrogen, amino, cyano, formyl, or for a radical of the series alkyl, alkoxy, alkylamino, dialkylamino, alkylcarbonyl or alkoxycarbonyl, each with 1 to 6 carbon atoms in each case optionally substituted by cyano, halogen or C -C-alkoxy the alkyl groups, or represents in each case optionally substituted by halogen alkenyl or alkynyl each having 2 to 6 carbon atoms, or represents optionally substituted by cyano or halogen cycloalkyl having 3 to 6 carbon atoms, and

R ⁸ for hydrogen, halogen, or for each optionally by

Cyano, halogen or C 1 -C 4 -alkoxy substituted radical of the series alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl groups, or for a radical of the series alkenyl which is optionally substituted by halogen , Alkenyloxy, alkenylthio, alkenylamino, alkynyl, alkynyloxy or alkynylthio each having 2 to 6 carbon atoms, or for a radical of the series cycloalkyl, cycloalkyloxy, cycloalkylthio or cycloalkylamino each having 3 to 6 carbon atoms each optionally substituted by cyano or halogen stands, or together with R ⁷ for alkanediyl (alkylene) with 2 to

6 carbon atoms.

The invention relates in particular to compounds of the formula (I) in which

m represents the numbers 0, 1, 2 or 3,

n represents the numbers 0, 1 or 2,

Q represents O, S, SO or SO ₂ ,

R ^{1 represents} hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by fluorine and / or chlorine, R ^{2 represents} hydrogen or methyl, ethyl, n- or i-propyl, n- or i-butyl which is optionally substituted by fluorine and / or chlorine,

X for hydroxy, mercapto, amino, hydroxyamino, nitro, formyl, carboxy, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for any substituted by cyano, fluorine, chlorine, methoxy or ethoxy

Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, Ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, propylsulfinyl, methylsulfonyl, ethylsulfonyl, propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n -, i-, s- or t-butylamino, dimethylamino,

Diethylamino, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl,

Y for nitro, carboxy, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for methyl, ethyl, n- or i-propyl, n-, i-, n-, i-, optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio,

Ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, and

Z represents one of the groupings below

wherein

R ³ for hydrogen, cyano, formyl, or for each optionally by

Cyano, fluorine, chlorine, methoxy or ethoxy substituted methyl,

Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl,

Methoxycarbonyl or ethoxycarbonyl, or for propenyl, butenyl, which are each optionally substituted by fluorine, chlorine or bromine,

Propynyl or butynyl,

R ^{4 represents} hydrogen, cyano, formyl, or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, Propionyl, Methoxycarbonyl or ethoxycarbonyl, or represents propenyl, butenyl, propynyl or butynyl which is optionally substituted by fluorine, chlorine or bromine,

R ⁵ for hydrogen, cyano, formyl, or for each optionally by

Cyano, fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, or for each optionally by fluorine, chlorine or bromine-substituted propenyl, butenyl, propynyl or butynyl,

R ⁶ for hydrogen, cyano, formyl, or for each optionally by

Cyano, fluorine, chlorine, methoxy or ethoxy substituted methyl,

Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl,

Propynyl or butynyl,

R ^{7 represents} hydrogen, amino, cyano, formyl, or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino,

Ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, or represents in each case optionally substituted by fluorine, chlorine or bromine, ^'s propenyl, butenyl , Propynyl or butynyl, or represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine or bromine, and

R ^{8 represents} hydrogen, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, Ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, or for each optionally by Fluorine, chlorine or bromine substituted propenyl, butenyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino, butenylamino, propynyl, butynyl, propynyloxy, butynyloxy, propynylthio or butynylthio, or for cyclopropyl, cyclobutyl optionally substituted by cyano, fluorine, chlorine or bromine , Cyclopentyl, Cyclohexyl, Cyclopropyloxy, Cyclobutyloxy, Cyclopentyloxy, Cyclohexyloxy, Cyclopropylthio, Cyclobutylthio, Cyclopentylthio, Cyclohexylthio, Cyclopropylamino, Cyclobutylamino, Cyclopentylamino or Cyclohexylamino.

Arylalkyl compounds of the general formula (I) in which

represents one of the groupings below

The general or preferred radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.

If, for example, 4- [4- (2,4-difluorophenylmethylthio) phenyl] -1-ethoxycarbonyl semicarbazide is used as the starting material, the course of the reaction in process (a) according to the invention can be outlined using the following formula:

If, for example, 1- [4- (2,5-dichlorophenylmethylsulfonyl) phenyl] -4-methyl-semicarbazide and phosgene are used as starting materials, the course of the reaction in process (b) according to the invention can be outlined using the following formula:

If, for example, 1- (3-chloro-4-fluorophenylsulfinyl) -1- (4-bromo-3-methylphenyl) ethane and 4-methyl-5-trifluoromethyl-2,4-dihydro-3H are used -l, 2,4-triazol-3-one as starting materials, the course of the reaction in process (c) according to the invention can be outlined by the following formula:

If, for example, 3-cyano-phenylmethyl chloride and 4-difluoromethyl-5-methyl-2- (2-fluoro-4-hydroxy-phenyl) -2,4-dihydro-3H-l, 2,4-triazol-3-one are used as starting materials, the course of the reaction in process (d) according to the invention can be outlined using the following formula:

Formula (II) provides a general definition of the 4-aryl-semicarbazides to be used as starting materials in process (a) according to the invention for the preparation of compounds of the formula (I). In the formula (II), m, n, Q, R ¹ , R ² , R ³ , R ⁴ , X and Y preferably or in particular have those meanings which have already been mentioned above in

Connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for m, n, Q, R ¹ , R ² , R ³ , R ⁴ , X and Y; R preferably represents alkyl having 1 to 4 carbon atoms, in particular methyl or ethyl.

The starting materials of formula (II) are not yet known from the literature; as new substances they are also the subject of the present application.

The new 4-aryl-semicarbazides of the general formula (II) are obtained if aminoarenes of the general formula (VIII)

in which

m, n, Q, R ¹ , R ² , X and Y have the meanings given above,

with phosgene or diphosgene (trichloroethyl chloroformate), if appropriate in the presence of a diluent, such as, for example, ethyl acetate, at temperatures between 0 ° C. and 50 ° C. and then with a hydrazine carboxylic acid ester of the general formula (IX)

in which

R, R ⁴ and R ^{5 have} the meanings given above,

optionally in the presence of a diluent, such as toluene, at temperatures between 10 ° C and 120 ° C (see the preparation examples)

The aminoarenes of the general formula (VIII) required as precursors are known and / or can be prepared by known processes (cf. US Pat. No. 5,399,543).

The hydrazine carboxylic acid esters of the general formula (IX) which are also required as precursors are known synthetic chemicals

The process (b) according to the invention for the preparation of compounds of

Formula (I) to be used as starting materials 1 - aryl-semicarbazides are generally defined by the formula (III) In the formula (III) m, n, Q, R ¹ , R ² , R ⁵ , R ⁶ , X have and Y preferably or in particular those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for m, n, Q, R ¹ , R ² , R ⁵ , R ⁶ , X and Y have been specified, R preferably represents alkyl having 1 to 4 carbon atoms, in particular methyl or ethyl

The starting materials of the formula (III) are not yet known from the literature; they are also the subject of the present application as new substances

The new l-aryl-semicarbazides of the general formula (III) are obtained if hydrazinoarenes of the general formula (X)

in which

m, n, Q, R ¹ , R ² , R ⁶ , X and Y have the meanings given above,

with isocyanates of the general formula (XI)

R ⁵ -N = C = O (XI)

in which

R ^{5 has} the meaning given above,

optionally in the presence of a diluent, such as, for example, toluene or chlorobenzene, and optionally in the presence of a basic reaction auxiliary, such as, for example, sodium or potassium hydride, potassium t-butoxide, triethylamine or ethyldiisopropylamine, at temperatures between 10 ° C. and 150 ° C implements The hydrazinoarenes of the general formula (X) required as precursors are known and / or can be prepared by known processes (cf. US 5262390)

The isocyanates of the general formula (XI) which are also required as precursors are known synthetic chemicals.

The haloarenes to be used as starting materials in the process (c) according to the invention for the preparation of compounds of the formula (I) are generally defined by the formula (IV). In the formula (IV) m, n, Q, R ¹ , R ² , X and Y preferably or in particular those meanings which have already been given above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for m, n, Q, R ¹ , R ² , X and Y, X ¹ preferably represents fluorine, chlorine or bromine, in particular fluorine or chlorine

The starting materials of the formula (IV) are known and / or can be prepared by known processes (cf. DE 2526358, US 4249934, US 5262390, WO

9621647)

The heterocyclic compounds to be used further as starting materials in process (c) according to the invention are generally defined by the formula (V). In formula (V) Z preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds according to the invention of formula (I) preferably or as particularly preferred for Z was specified

The starting materials of the general formula (V) are known and / or can be prepared by known processes (cf. J Org Chem 56 (1991), 5643-5651, DE 4416868).

The arylalkyl halides to be used as starting materials in the process (d) according to the invention for the preparation of compounds of the formula (I) are generally defined by the formula (VI). In the formula (VI), m, R ¹ , R ² and X preferably or in particular have those Meanings which have already been given above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for m, R ¹ , R ² and X, X ² preferably represents chlorine, bromine or iodine, in particular chlorine or bromine The starting materials of the general formula (VI) are known synthetic chemicals

The arenes to be used further as starting materials in process (d) according to the invention are generally defined by the formula (VII). In formula (VII), N, Y and Z preferably or in particular have those meanings which have already been mentioned above in connection with the description of the inventive Compounds of formula (I) preferably or as particularly preferred for n, Y and Z have been indicated, Q ¹ preferably represents O or S, in particular O.

The starting materials of the general formula (VII) are known and / or can be prepared by processes known per se (cf. US 5262390)

Suitable reaction auxiliaries for processes (a) to (d) according to the invention are generally the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates and hydrides , hydroxides or alkanolates, such as sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium, potassium or calcium carbonate,

Sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, ethanolate, -n- or -i- propanolate, -n-, -i-, -s- or -t-butanolate, and also also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine , Dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6 -Dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyfidine, N-methyl-piperidine, 1,4-diazabicyclo [2 , 2,2] octane (DABCO), 1,5-diazabicyclo [4,3,0] non-5-ene (DBN), or 1.8

Diazabicyclo [5,4,0] -undec-7-ene (DBU).

Suitable diluents for carrying out processes (a) to (d) according to the invention are, above all, inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene,

Dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride, ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether, ketones such as acetone, butanone or methyl isobutyl ketone nitrile or butyronitrile, amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphoric acid triamide, esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water

The reaction temperatures can be varied within a substantial range when carrying out processes (a) to (d) according to the invention. In general, temperatures between -20 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.

Processes (a) to (d) according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.

To carry out the processes according to the invention, the starting materials are generally used in approximately aquimolar amounts. However, it is also possible to use one of the components in a larger excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is carried out in all - Agitated several hours at the required temperature. Working up is carried out according to customary methods (see the production examples)

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, in particular, as weed killers. Weeds in the broadest sense are understood to mean all plants which grow up in places where they are undesirable, whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used

The active compounds according to the invention can be used, for example, in the following plants

Dicotyledon weeds of the genera Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca,

Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium,

Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veromca, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum

Dicotyledon cultures of the genera Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita

Monocotyledonous weeds of the genera Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharisemumum, Scirpum Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera

Monocot cultures of the genera Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium

However, the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants.

Depending on the concentration, the compounds are suitable for total weed control, for example on industrial and rail tracks and on paths and squares with and without tree cover. Likewise, the compounds for weed control in permanent crops, for example forest, ornamental wood, fruit, wine, Citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants are used on ornamental and sports turf and pasture land and for selective weed control in annual crops.

The compounds of the formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon crops, such as, for example, maize and wheat, both pre-emergence and post-emergence.

method

The active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension emulsion concentrates, natural and synthetic substances impregnated with active substances, and very fine encapsulations in polymeric substances These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents

If water is used as an extender, organic substances can also be used

Solvents are used as auxiliary solvents. Liquid solvents are essentially aromatics, such as xylene, toluene, or alkyl naphthalene, chlorinated aromatics and chlorinated ahphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, ahphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions , mineral and vegetable

Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl sobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water

Solid carrier materials that come into question are, for example, ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmole lumps or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, and solid carrier materials for granules Question e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust,

Coconut shells, corn cobs and tobacco stalks, as emulsifiers and / or foam-generating agents are suitable, for example, ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates and aryl sulfonates - Hydrolysates, as dispersants are, for example, lignin sulfite and

Methyl cellulose

Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalene and lecithins and synthetic phosphides, can be used in the formulations. Further additives can be mineral and vegetable oils his

Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes Substances and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.

The formulations generally contain between 0.1 and 95 percent by weight of active compound; preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.

Known herbicides are suitable for the mixtures, for example

Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Asulam, Atrazine, Azimsulfuron, Benazolin, Benfuresate, Bensulfuron (-methyl), Bentazon, Benzofenap - ethyloylpropyl ), Bialaphos, Bifenox, Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butylate, Cafenstrole, Carbetamides, Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinmethylin, Clethodimphonon, Clonimphonon, Cinosimphuron, Cinosulfuron) Clomazone, Clopyralid, Clopyrasulfuron, Cloransulam (-methyl), Cumyluron, Cyanazines, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dinitrramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, EPTC, Esproc

Ethalfluralin, ethametsulfuron (-methyl), ethofumesate, ethoxyfen, etobenzanide, fenoxaprop (-ethyl), flamprop (-isopropyl), flamprop (-isopropyl-L), flamprop (- methyl), flazasulfuron, fluazifop (-butyl), flumetsulam, Flumiclorac (-pentyl), flumioxazin, flumipropyn, fluometuron, fluorochloridone, fluoroglycofen (- ethyl), flupoxam, flupropacil, flurenol, fluridone, fluroxypyr, flurprimidol,

Flurtamone, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropyl-ammonium), Halosafen, Haloxyfop (-ethoxyethyl), Hexazinone, Imazamethabenz (- methyl), Imazamethapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Ioxynilonuron Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Metamitron, Metazachlor,

Methabenzthiazuron, Metobenzuron, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Napro-anilide, Napropamide, Neburon, Nicosulfuron, Norflurazon Orbencarb, Oryzalin, Oxyzalin, Oxyzalin , Pretilachlor, primisulfuron (-methyl), prometryn, propachlor, propanil, propaquizafop, propyzamides, prosulfocarb, prosulfuron, pyrazolates, pyrazosulfuron (-ethyl), pyrazoxyfen, pyributicarb, pyridates, pyrithiobac (-sodium), quinine, quinine, quinine Quizalofop (-ethyl), Quizalofop (-p-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate,

Tebutam, tebuthiuron, terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron (-methyl), triculfurifluronophenifluronophenifluronophenl, triclurifuronophenyl trifluorophenyl trifluorophenyl trifluorophenyl trifluorophenyl trifluorophenyl trifluorophenyl trifluoronyl trifluoride trifluoronyl trifluoric acid

A mixture with other known active ingredients, such as fungicides,

Insecticides, acaricides, nematicides, bird repellants, plant nutrients and soil structure improvers are possible

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. The use is carried out in a customary manner, for example by pouring, spraying, spraying, Scatter.

The active compounds according to the invention can be applied both before and after the plants emerge. They can also be incorporated into the soil before sowing

The amount of active ingredient used can vary over a wide range. It depends essentially on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha

The preparation and use of the active compounds according to the invention can be seen from the examples below Manufacturing examples:

example 1

(Method (a))

5.0 g (13 mmol) of l-ethoxycarbonyl-2-methyl-4- [4- (4-chlorophenyl-methoxy) -2-fluorophenylj-semicarbazide become one at room temperature (20 ° C.) with stirring Solution of 7.2 g (0.13 mol) of potassium hydroxide in 32 ml of water was added and the reaction mixture was stirred at 80 ° C. for one hour. After cooling to room temperature, the pH of the mixture is adjusted to 5 by adding 2N hydrochloric acid and the crystalline product is isolated by suction.

4.0 g (89% of theory) of 4 - [(4-chlorophenyl-methoxy) -2-fluorophenyl] -l-methyl-1,2,4-triazoline-2,5-dione from Melting point 172 ° C.

Example 2

(Follow-up implementation) A mixture of 2.0 g (5.7 mmol) of 4 - [(4-chlorophenyl-methoxy) -2-fluorophenyl] -1-methyl-1,2,4-triazoline-2,5-dione , 1.57 g (11.4 mmol) of potassium carbonate and 30 ml of N, N-dimethylformamide is stirred at 60 ° C. for one hour. The mixture is then heated to 80 ° C. and chlorodifluoromethane is introduced at this temperature for 2 hours. After cooling to room temperature (approx. 20 ° C.), the mixture is poured into approximately the same volume of 1N hydrochloric acid and shaken with ethyl acetate. The organic phase is separated off, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum and the residue is purified by column chromatography (silica gel / methylene chloride).

1.6 g (70% of theory) of 4 - [(4-chlorophenyl-methoxy) -2-fluorophenyl] -2-difluoromethyl-l-methyl-l, 2,4-triazolin-2, 5-dione with a melting point of 85 ° C.

Example 3

(Follow-up implementation)

A mixture of 1.5 g (4.3 mmol) of 4 - [(4-chlorophenyl-methoxy) -2-fluorophenyl] -l-methyl-1,2,4-triazoline-2,5-dione , 0.6 g (4.7 mmol) of dimethyl sulfate, 0.65 g (4.7 mmol) of potassium carbonate and 50 ml of acetonitrile is stirred for 18 hours at room temperature (approx. 20 ° C.) and then concentrated in a water jet vacuum. The residue is digested with ethyl acetate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum.

1.1 g (71% of theory) of 4 - [(4-chlorophenyl-methoxy) -2-fluorophenyl] -1, 2-dimethyl-l, 2,4-triazoline-2,5- dione as a crystalline residue with a melting point of 132 ° C. Analogously to preparation examples 1 to 3 and in accordance with the general description of the preparation processes according to the invention, it is also possible, for example, to prepare the compounds of the formula (I) listed in table 1 below

Table 1 Examples of the compounds of the formula (I)

Starting materials of formula (II)

Example (11-1)

4.0 g (16 mmol) of l-amino-2-fluoro-4- (4-chlorophenyl-methoxy) benzene are placed in 100 ml of ethyl acetate and 6.3 g at room temperature (approx. 20 ° C.) (32 mmol) chloroformic acid trichloromethyl ester is added dropwise with stirring. The mixture is heated under reflux for 2 hours and, after cooling, is concentrated in a water jet vacuum. 100 ml of toluene and 2.2 g (16 mmol) of 2-methyl-hydrazine carboxylic acid ethyl ester are added and the residue The reaction mixture is then heated under reflux and stirred for 3 hours. After cooling, the mixture is concentrated in a water jet vacuum, the residue is taken up in ethyl acetate and filtered through silica gel. The solvent is carefully distilled off from the filtrate in a water jet vacuum

6.0 g (95% of theory) of l-ethoxycarbonyl-2-methyl-4- [4- (4-chlorophenyl-methoxy) -2-fluoro-phenyl] -semicarbazide are obtained as a crystalline residue of melting point 108 ° C.

Examples of use:

Example A

Pre-emergence test

Solvent 5 parts by weight of acetone emulsifier 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration

Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area. The concentration of the spray boil is chosen so that the desired amounts of active compound are found in 1,000 l of water / ha be applied

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control

Mean it

0% = no effect (like untreated control)

100% = total annihilation

In this test, at application rates between 1000 g and 2000 g per hectare, the compounds according to Preparation Examples 2 and 3, for example, show good activity against weeds such as Abutilon (100%), Amaranthus (100 %), Sinapis (100%) and Galium (100%) Example B

Post emergence test

Solvent 5 parts by weight of acetone

Emulsifier - 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, mix 1

Part by weight of active ingredient with the stated amount of solvent, adds the stated amount of emulsifier and dilutes the concentrate with water to the desired concentration

Test plants which have a height of 5-15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area. The concentration of the spray mixture is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

Mean it

0% = no effect (like untreated control) 100% = total destruction

In this test, at application rates of 500 g / ha, for example, the compounds according to production examples 2 and 3 show with good compatibility

Cultivated plants, such as wheat (10%), strong action against weeds such as Abutilon (100%), Amaranthus (100%), Datura (100%), Solanum (100%), Xanthium (100%) and Setaria (95% )

Claims

claims

Arylalkyl compounds of the general formula (I)

characterized in that

m represents the numbers 0 to 5,

n stands for the numbers 0 to 4,

Q represents O, S, SO or SO ₂ ,

R ^{1 represents} hydrogen or optionally substituted alkyl,

R ^{2 represents} hydrogen or optionally substituted alkyl,

X for hydroxy, mercapto, amino, hydroxyamino, nitro, formyl, carboxy, cyano, carbamoyl, thiocarbamoyl, halogen, or for a radical of the series alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylamino which is optionally substituted by cyano, halogen or alkoxy , Dialkylamino, alkylcarbonyl or alkoxycarbonyl,

Y represents nitro, carboxy, cyano, carbamoyl, thiocarbamoyl, halogen, or a radical of the series alkyl, alkoxy, alkylthio, alkylsulfmyl or alkylsulfonyl which is optionally substituted by cyano, halogen or alkoxy, and

Z represents one of the groupings below

wherein

R ^{3 represents} hydrogen, cyano, formyl, or a radical of the series alkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl or alkynyl which is optionally substituted by cyano, halogen or alkoxy,

R ^{8 represents} hydrogen, halogen, or a radical which is optionally substituted by cyano, halogen or alkoxy

Series alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylamino, dialkylamino, alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkynyl, alkynyloxy, alkynylthio, cycloalkyl, Cycloalkyloxy, cycloalkylthio or cycloalkylamino, or together with R ^{7 is} alkanediyl (alkylene).

Process for the preparation of the arylalkyl compounds of the general formula

00,

in which

m, n, Q, R ¹ , R ² , X, Y and Z have the meanings given in claim 1, characterized in that

(a) 4-aryl-semicarbazides of the general formula (II)

in which

m, n, Q, R ¹ , R ² , R ³ , R ⁴ , X and Y have the meanings given in claim 1 and

R represents alkyl, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, condensed cyclizing and, if appropriate, subsequently carrying out electrophilic or nucleophilic substitution reactions as part of the definition of substituents,

or that one

(b) l-aryl semicarbazides of the general formula (III)

in which

m, n, Q, R ¹ , R ² , R ⁵ , R ⁶ , X and Y have the meanings given in claim 1,

or that one

(c) haloarenes of the general formula (IV)

in which

m, n, Q, R ¹ , R ² , X and Y have the meanings given in Claim 1 and

X ^{1 represents} halogen,

with heterocyclic compounds of the general formula (V)

Z-H (V)

in which

has the meaning given above,

or that one

(d) arylalkyl halides of the general formula (VI)

in which m, R ¹ , R ² and X have the meanings given above and

X ^{2 represents} halogen,

with arenes of the general formula (VII)

in which

n, Y and Z have the meanings given in claim 1 and

Q ^{1 represents} oxygen or sulfur, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent and, if appropriate, subsequently carries out electrophilic or nucleophilic substitution reactions as part of the definition of the substituents

3. arylalkyl compounds of general formula (I) according to claim 1, characterized in that

m represents the numbers 0 to 4,

n represents the numbers 0 to 3,

Q represents O, S, SO or SO ₂ ,

R ^{1 represents} hydrogen or optionally substituted by halogen

Alkyl having 1 to 6 carbon atoms,

R ^{2 represents} hydrogen or alkyl which has 1 to 6 carbon atoms and is optionally substituted by halogen, X for hydroxy, mercapto, amino, hydroxyamino, nitro, formyl, carboxy, cyano, carbamoyl, thiocarbamoyl, halogen, or for a radical of the series alkyl, alkoxy, alkylthio, alkylsulfmyl which is optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy , Alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups,

Y stands for nitro, carboxy, cyano, carbamoyl, thiocarbamoyl, halogen, or for a radical of the series alkyl, alkoxy, alkylthio, alkylsulfmyl or alkylsulfonyl each having 1 to 6 carbon atoms in each of which is optionally substituted by cyano, halogen or C1-C4alkoxy Stands for alkyl groups, and

Z represents one of the groupings below

wherein

R ³ for hydrogen, cyano, formyl, or for a radical optionally substituted by cyano, halogen or CJ-C4-alkoxy

Series of alkyl, alkylcarbonyl or alkoxycarbonyl each with 1 to 6

6 carbon atoms,

R ^{4 represents} hydrogen, cyano, formyl, or a radical of the series alkyl, alkylcarbonyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or CJ-C4-alkoxy, each having 1 to 6 carbon atoms in the alkyl groups, or each optionally substituted by halogen Is alkenyl or alkynyl each having 2 to 6 carbon atoms,

R ^{5 represents} hydrogen, cyano, formyl, or a radical which is optionally substituted by cyano, halogen or C _] -C4-alkoxy A series of alkyl, alkylcarbonyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups, or represents in each case optionally substituted by halogen-substituted alkenyl or alkynyl each having 2 to 6 carbon atoms,

R ^{6 represents} hydrogen, cyano, formyl, or a radical of the series alkyl, alkylcarbonyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C1-C4alkoxy, each having 1 to 6 carbon atoms in the alkyl groups, or each optionally substituted by halogen Is alkenyl or alkynyl each having 2 to 6 carbon atoms,

R ^{7 represents} hydrogen, amino, cyano, formyl, or a radical of the series alkyl, alkoxy, alkylamino, dialkylamino, alkylcarbonyl or alkoxycarbonyl, each of which has 1 to 6 carbon atoms in the alkyl groups and is optionally substituted by cyano, halogen or Cj-C4-alkoxy , or represents a radical of the series alkenyl, alkynyl each having 2 to 6 carbon atoms which is optionally substituted by halogen, or represents cycloalkyl having 3 to 6 carbon atoms optionally substituted by cyano or halogen, and

R ^{8 represents} hydrogen, halogen, or a radical in the series which is optionally substituted by cyano, halogen or C j -C4-alkoxy

Alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl groups, or for an optionally substituted by halogen radical from the series alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkynyl, alkynyloxy or alkynylthio each represents 2 to 6 carbon atoms, or represents a radical of the series cycloalkyl, cycloalkyloxy, cycloalkylthio or cycloalkylamino, each optionally substituted by cyano or halogen, each having 3 to 6 carbon atoms, or together with R ^{7 represents} alkanediyl (alkylene) having 2 to 6 carbon atoms stands.

4. 4-aryl-semicarbazides of the general formula (II)

characterized in that

m represents the numbers 0 to 5,

represents the numbers 0 to 4,

Q represents O, S, SO or SO ₂ ,

R ^{1 represents} hydrogen or optionally substituted alkyl,

R ^{2 represents} hydrogen or optionally substituted alkyl,

Y represents nitro, carboxy, cyano, carbamoyl, thiocarbamoyl, halogen, or a radical of the series alkyl, alkoxy, alkylthio, alkylsulfmyl or alkylsulfonyl which is optionally substituted by cyano, halogen or alkoxy, R ^{3 represents} hydrogen, cyano, formyl, or a radical of the series alkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl or alkynyl which is optionally substituted by cyano, halogen or alkoxy,

R ^{4 represents} hydrogen, cyano, formyl, or a radical of the series alkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl or alkynyl which is optionally substituted by cyano, halogen or alkoxy, and

R represents alkyl.

1 - aryl semicarbaxides of the general formula (III)

characterized in that

m represents the numbers 0 to 5,

n stands for the numbers 0 to 4,

Q represents O, S, SO or SO ₂ ,

R ^{1 represents} hydrogen or optionally substituted alkyl,

R ^{2 represents} hydrogen or optionally substituted alkyl,

X for hydroxy, mercapto, amino, hydroxyamino, nitro, formyl, carboxy, cyano, carbamoyl, thiocarbamoyl, halogen, or for a radical of the series alkyl, alkoxy, alkylthio, alkylsulfmyl which is optionally substituted by cyano, halogen or alkoxy, Alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl or alkoxycarbonyl,

Y represents nitro, carboxy, cyano, carbamoyl, thiocarbamoyl, halogen, or a radical of the series alkyl, alkoxy, alkylthio, alkylsulfmyl or alkylsulfonyl which is optionally substituted by cyano, halogen or alkoxy,

R ^{5 represents} hydrogen, cyano, formyl, or a radical of the series alkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl or alkynyl which is optionally substituted by cyano, halogen or alkoxy and

R ^{6 represents} hydrogen, cyano, formyl, or a radical of the series alkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl or alkynyl which is optionally substituted by cyano, halogen or alkoxy

Herbicidal agents, characterized in that they contain at least one arylalkyl compound of the formula (I) according to Claim 1

Process for controlling unwanted plants, characterized in that arylalkyl compounds of the formula (I) according to Claim 1 are allowed to act on undesired plants and / or their habitat

Use of arylalkyl compounds of the formula (I) according to Claim 1 for combating undesirable plants

Process for the preparation of herbicidal compositions, characterized in that arylalkyl compounds of the formula (I) according to Claim 1 are mixed with extenders and / or surface-active substances