WO2001023356A1 - Substituted n-phenyl-phenoxy nicotinic acid-(thio) amides and their use as herbicides - Google Patents

Abstract

The invention relates to novel substituted N-phenyl-phenoxy nicotinic acid-(thio)amides of general formula (I) in which: Q represents O (oxygen) or S (sulfur); R<1> represents hydrogen or optionally substituted alkyl, alkenyl or alkynyl; R<2> represents hydrogen, halogen or optionally substituted alkyl; R<3> represents cyano, halogen, SF5 or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl; R<4> represents hydrogen, cyano, halogen or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl; R<5> represents nitro, cyano, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, and -in the case that R<1> is not hydrogen- also represents hydrogen; R<6> represents hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, and; R<7> represents hydrogen, nitro, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, -with the provision that R<6> does not represent hydrogen or methyl if R<5> represents methyl and R<2> or R<7> represents hydrogen- and with the provision that R<6> does not represent hydrogen if R<5> and R<7> represent halogen and R<2> represents hydrogen. The invention also relates to a method for producing the novel compounds and to their use as herbicides.

Description

SUBSTITUTED N-PHENYL-PHENOXYNICOTIC ACID (THIO) AMIDES AND THEIR END AND AS HERBICIDES

The invention relates to new substituted N-phenyl-phenoxynicotinsäure- (thio) amides, 5 processes for their preparation and their use as herbicides.

Substituted N-phenylphenoxynicotamides, e.g. the compound N- (2,4-difluorophenyl) -2- (3-trifluoromethylphenoxy) -3-pyridine-carboxamide (diflufenican) are already known as herbicidally active substances (cf. EP-A-5301 1; Pestic See 18 10 (1987), 15-28; see also JP-A-02178266 - cited in Chem. Abstracts 113: 226429).

The new substituted N-phenylphenoxynicotinic acid (thio) amides of the general formula (I)

15 in which

Q represents O (oxygen) or S (sulfur),

R ^! for hydrogen or for optionally substituted alkyl or alkenyl

20 or alkynyl,

R ^{~ represents} hydrogen, halogen or optionally substituted alkyl,

R ³ for cyano. Halogen, SF ₅ , or for optionally optionally substituted alkyl,

25 is alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, R ⁴ for hydrogen, cyano, halogen, or for optionally substituted alkyl, alkoxy, alkylthio. Alkylsulfinyl or alkylsulfonyl,

R ^{5 represents} nitro, cyano, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, and - in the event that R ^{1 is} different from hydrogen - also represents hydrogen,

R ° represents hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, and

R 'for hydrogen, nitro, cyano, carbamoyl. Thiocarbamoyl, halogen, or optionally substituted alkyl,

with the proviso that R is not halogen or methyl when R ^{5 is} methyl and R ² or R ^{7 is} hydrogen,

and with the proviso that R ^{6 is} not hydrogen when R ⁵ and R ^{7 are} halogen and R ^{2 is} hydrogen,

found.

In the definitions, the hydrocarbon chains, such as alkyl, are also straight-chain or branched, in each case in conjunction with heteroatoms, such as in alkoxy.

Preferred substituents or preferred ranges of the radicals present above and below are defined below.

Q is preferably O (oxygen).

R ¹ preferably represents hydrogen, optionally by cyano, halogen,

Ci-C Alkoxv. C-Cj-Alkvlthio. C d-Alkvlsulfϊ l or Ci-O-Alkvl- sulfonyl-substituted alkyl having 1 to 5 carbon atoms, or for alkenyl or alkynyl each optionally substituted by cyano or halogen, each having 3 to 5 carbon atoms.

R ² preferably represents hydrogen, halogen or optionally by cyano,

Halogen or -CC alkoxy substituted alkyl having 1 to 5 carbon atoms.

R ³ preferably represents cyano, halogen, SF ₅ , or alkyl, alkoxy optionally substituted by cyano, halogen or C 1 -C ₄ -alkoxy,

Alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 5 carbon atoms.

R ⁴ preferably represents hydrogen, cyano, halogen, or alkyl, alkoxy which is optionally substituted by cyano, halogen or C 1 -C 8 -alkoxy,

Alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 5 carbon atoms.

R ⁵ preferably represents nitro, cyano, carbamoyl, thiocarbamoyl, halogen, or for alkyl optionally substituted by cyano, halogen, C 1 -C ₄ -alkoxy, C 1 -C ₄ -alkylthio, dC - alkylsulfinyl or Cj-C - alkylsulfonyl 1 to 5

Carbon atoms, and - if R ^{1 is} different from hydrogen - also for hydrogen.

R ⁶ preferably represents hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl,

Halogen, or represents optionally cyano-, halogen, Cj-C ₄ - alkoxy, CJ-C ₄ alkylthio, Cι-C -Alkylsulfιnyl or Cι-C ₄ -alkylsulfonyl-substituted alkyl having 1 to 5 carbon atoms.

R ⁷ preferably represents hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl,

Halogen, or for optionally by cyano. Halogen, CrO-alkoxy, Cj- C - alkylthio, -CC alkyl sulfonyl or dC ₄ - alkyl sulfonyl substituted alkyl having 1 to 5 carbon atoms.

R ¹ particularly preferably represents hydrogen, in each case optionally by cyano, fluorine, chlorine, methoxy or ethoxy, methylthio or ethylthio,

Methylsulfinyl or ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or for propenyl, butenyl, propynyl optionally substituted by cyano, fluorine, chlorine or bromine or butinyl.

R ² particularly preferably represents hydrogen, fluorine, chlorine, bromine, or in each case methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy.

R ³ particularly preferably represents cyano, fluorine, chlorine, bromine, SF ₅ , or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or, in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfmyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl.

R ⁴ particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy - Propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl.

R ⁵ particularly preferably represents nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or in each case optionally by cyano, fluorine,

Chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i- Propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl substituted methyl, ethyl, n- or i-propyl, and - in the event that R is different from hydrogen - also for Hydrogen.

R ⁶ particularly preferably represents hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or l-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl substituted methyl, ethyl, n- or i-propyl.

R ⁷ particularly preferably represents hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or optionally cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or l-

Propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl substituted methyl, ethyl, n- or i-propyl.

R ¹ very particularly preferably represents hydrogen, each methyl or ethyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or propenyl or propynyl each optionally substituted by fluorine or chlorine.

R ² very particularly preferably represents hydrogen or fluorine. Chlorine, bromine, or for each optionally by fluorine, chlorine. Methoxy or ethoxy substituted methyl or ethyl

R 'very particularly preferably represents cyano, fluorine. Chlorine, bromine, or optionally substituted by fluorine, chlorine, methoxy or ethoxy lertes methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.

R ⁴ very particularly preferably represents cyano, fluorine, chlorine, bromine or methyl, ethyl, methoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, which are each optionally substituted by fluorine, chlorine, methoxy or ethoxy.

R ^ very particularly preferably stands for cyano, fluorine, chlorine, bromine, or for methyl or ethyl substituted in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, and - for the Case that R ^{1 is} different from hydrogen - also for hydrogen.

R ° very particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine,

Bromine, or for each methyl or ethyl substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.

R ⁷ very particularly preferably represents hydrogen, cyano. Fluorine, chlorine, bromine, or for each methyl or ethyl substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.

R ¹ most preferably represents hydrogen or propyl

R is most preferred for on Hydrogen or meth \ ^'

R ^" most preferably stands for Tπfluormethvl

R ⁴ most preferably stands for hydrogen R ⁵ most preferably represents hydrogen, fluorine, chlorine, methyl, ethyl or ethylthio substituted by methyl.

R ⁶ most preferably represents hydrogen, nitro, cyano, fluorine, chlorine, methyl, ethyl or trifluoromethyl.

R ⁷ most preferably represents hydrogen, cyano, fluorine, chlorine, bromine, methyl, ethyl or trifluoromethyl.

According to the invention, preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as preferred.

According to the invention, particular preference is given to the compounds of the formula (I) in which a combination of those listed as particularly preferred above

Meanings exist.

According to the invention, very particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.

Most preferred according to the invention are the compounds of formula (I) in which there is a combination of the meanings listed as most preferred above.

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 residual definitions can be combined with one another, that is, also between the specified preferred ranges. The provisions formulated above for the general definition of the radicals in formula (I) also apply here

A group to be particularly emphasized are those compounds of the formula (I), m which

Q stands for O (oxygen),

R ^{1 represents} hydrogen,

R ² for hydrogen, fluorine, chlorine. Bromine, or represents methyl or ethyl optionally substituted by fluorine or chlorine,

R ³ for cyano, fluorine, chlorine, bromine, or for each methyl, methoxy, methylthio, methylsulfinyl or optionally substituted by fluorine or chlorine

Methylsulfonyl,

R ^{4 represents} cyano, fluorine, chlorine, bromine, or methyl or methoxy which is optionally substituted by fluorine or chlorine,

R ^{^} for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy,

Methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or

Ethylsulfonyl is substituted methyl or ethyl,

R 'for hydrogen, nitro, cyano, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy. Methylthio, Eth \ l- thio, Methylsulfinyl, Ethylsulfιn> l Methylsulfonyl or Ethylsulfonyl substituted methyl or ethyl, and

R for hydrogen, cyano. Fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine. Methow Ethoxy, Methvlthio, Ethylthio, Meth \ 1- sulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl or ethyl,

with the proviso that R ^{6 is} not fluorine, chlorine, bromine or methyl if R ^{5 is} methyl and R ² or R ^{7 is} hydrogen

Another group to be particularly emphasized are those compounds of the formula (I) which

Q stands for O (oxygen),

R ^{1 represents} hydrogen,

R ² for hydrogen, fluorine, chlorine, bromine, or for each optionally by

Fluorine or chlorine substituted methyl or ethyl,

R for cyano, fluorine, chlorine, bromine, or for methyl, methoxy, methylthio which is optionally substituted by fluorine or chlorine. Methylsulfinyl or methylsulfonyl,

R ^{4 represents} cyano, fluorine, chlorine, bromine, or methyl or methoxy which is optionally substituted by fluorine or chlorine,

R ^{^ represents} fluorine or chlorine,

R ^(stands for nitro, cyano, fluorine, chlorine, bromine, or for methyl or ethyl optionally substituted in each case by fluorine or chlorine, and

R for cyano, fluorine, chlorine. Bromine, or represents methylene or ethylene optionally substituted by fluoi or chlorine Another group to be particularly emphasized are those compounds of the formula (I) in which

Q stands for O (oxygen),

R ^{1 represents} propinyl,

R ^{2 represents} hydrogen, fluorine, chlorine, bromine or methyl or ethyl which is in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy,

R ^{3 represents} cyano, fluorine, chlorine, bromine, or methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy,

R ^{4 stands} for cyano, fluorine, chlorine, bromine, or for methyl, ethyl, methoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, which are optionally substituted by fluorine, chlorine, methoxy or ethoxy,

R ^{5 stands} for hydrogen, cyano, fluorine, chlorine, bromine, or for methyl or ethyl substituted in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.

R ⁶ for hydrogen, nitro, cyano, fluorine, chlorine, bromine, or for each optionally by cyano. Fluorine, chlorine. Methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl is substituted methyl or ethyl, and R ^{7 stands} for hydrogen, cyano, fluorine, chlorine, bromine, or for methyl or ethyl substituted in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.

The new substituted N-phenyl-phenoxynicotinsäure- (thio) amides of the general formula (I) have interesting biological properties. They are particularly characterized by their strong herbicidal activity.

The new substituted N-phenyl-phenoxynicotinsäure- (thio) amides of the general formula (I) are obtained if one

(a) Phenoxynicotinic acid derivatives of the general formula (II)

in welcher

in which

Q, R ² , R ³ and R ^{4 have} the meaning given above and

Y represents halogen, imidazolyl, alkoxy, aryloxy or aralkoxy,

- or corresponding carboxylic anhydrides -

in welcherwith aniline derivatives of the general formula (III)

in which

R ¹ , R ⁵ , R ⁶ and R ^{7 have} the meaning given above,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

or if you

(b) Nicotinic acid derivatives of the general formula (IV)

in welcher

in which

Q, R ¹ , R ² , R ⁵ , R ⁶ and R ^{7 have} the meaning given above and

X represents halogen,

with substituted phenols of the general formula (V)

w elchei R³ und R⁴ die oben angegebene Bedeutung haben,

w elchei R ³ and R ^{4 have} the meaning given above,

- or with alkali metal salts of the compounds of formula (V) -

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

and, if appropriate, subsequently converting the compounds of the general formula (I) thus obtained into other compounds of the general formula (I) in the context of the substituent definition by customary methods.

If, for example, N-methyl-2,3,4-trifluoro-aniline and 2- (3-chlorophenoxy) -5-methyl-nicotinoyl chloride are used as starting materials, the reaction in process (a) according to the invention can be carried out by the following Formula scheme are outlined:

If, for example, 2-chloro-N- (4-fluoro-2-methyl-3-tπfluoιmethyl-phenyl) -nιcotιnsaureamιd and 3-Tπfluorτnethyl-phenol are used as starting materials, the reaction in process (b) according to the invention can be outlined by the following formula become

Formula (II) provides a general definition of the phenoxynicotic acid derivatives to be used as starting materials in process (a) according to the invention for the preparation of compounds of the general formula (I). In the general formula (II), Q, R ² , R ³ and R ⁴ preferably have those meanings which have already been mentioned above as preferred, particularly preferred, very particularly preferred or in connection with the description of the compounds of the general formula (I) according to the invention most preferably have been given for Q, R ² , R ³ and R ⁴ ; Y preferably represents fluorine, chlorine, bromine, imidazolyl, methoxy, ethoxy, phenoxy or benzyloxy, in particular chlorine

The starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. EP-A-53011, J. Med Chem. 18 (1975), 1-8)

The anilm derivatives used in the process (a) according to the invention for the preparation of compounds of the general formula (I) to be used further as starting materials are generally defined by the formula (III). In the general formula (III) R ¹ , R \ R and R preferably have those Meanings already mentioned above in connection with the description of the compounds according to the invention of the general my formula (I) have been given as preferred, particularly preferred, very particularly preferred or most preferred for R, R, R and R.

The starting materials of the general formula (III) are known and / or can be prepared by processes known per se (cf. J. Med. Chem. 33 (1990), 2 ^ - Phosphorus Sulfur 1 (1976), 11-18; DE -A-2018688, EP-A-316657, EP-A-799828).

With the exception of the compound 4-chloro-2- (l-methylthio-ethyl) -aniline (see Phosphorus Sulfur 1 (1976), 11-18) not yet known from the literature and with the exception of 4-chloro-2- ( l-methylthio-ethyl) -aniline as new substances also the subject of the present application are the aniline derivatives of the general formula (purple)

in welcher

in which

R ^] , R ⁶ and R ^{7 have} the meaning given above,

R ^{8 represents} -C ₃ - alkyl (especially methyl or ethyl) and

R ^{9 represents} Cj-C-alkyl (especially methyl, ethyl, n- or i-propyl).

The new aniline derivatives of the general formula (purple) are obtained if anilines of the general formula (IV)

in welcher R¹, R⁶ und R⁷ die oben angegebene Bedeutung haben,

in which R ¹ , R ⁶ and R ^{7 have} the meaning given above,

with dialkyl sulfides of the general formula (V)

in welcher

in which

R ⁸ and R ^{9 have} the meaning given above,

in the presence of a halogenating agent, e.g. Chlorine, bromine, N-chlorosuccinimide or N-bromosuccinimide, in the presence of an inert diluent, e.g. Methylene chloride or chloroform, at temperatures between -80 ° C and + 60 ° C, and then with an acid binder, such as Triethylamine or diisopropyl-ethylamine, treated at temperatures between 0 ° C and 120 ° C (see the preparation examples).

The compounds of the general formula (lilac) which can be prepared in this way can be converted in a customary manner by "hydrodesulfurization" (cf. EP-A-185128) into corresponding 2-alkylanilines (cf. the preparation examples).

Formula (IV) provides a general definition of the nicotinic acid derivatives to be used as starting materials in process (b) according to the invention for the preparation of compounds of the general formula (I). In the general formula (IV), Q, R ¹ , R ² , R ⁵ , R ⁶ and R ⁷ preferably have those meanings which have been particularly preferred above in connection with the description of the compounds of the general formula (I) according to the invention , very particularly preferably or most preferably for Q, R ¹ , R ² , R ⁵ , R ⁶ and R ⁷ ; X preferably represents fluorine, chlorine or bromine, in particular fluorine or chlorine. The starting materials of the general formula (IV) are known and / or can be prepared by processes known per se (cf. J Heterocycl Chem 19 (1982), 1093-1097, DE-A-261 1601, EP-A-256503, EP- A-545099)

The substituted phenols which are further to be used as starting materials in the process (b) according to the invention for the preparation of compounds of the general formula (I) are generally defined by the formula (V). In the general formula (V) R ³ and R ⁴ preferably have those meanings which have already been given above in connection with the description of the compounds of the general formula (I) according to the invention as preferred, particularly preferred, very particularly preferred or most preferred for R and R.

The starting materials of the general formula (V) are known organic synthetic chemicals

l- 4 Methvl-, 2,4-Dιmeth\ l 2 6-Dιmethvl-, 3,4-Dιmethyl- und 3,5-Dimethyl-pyridin, 5-Ethyl-2-methyl-pyridin, 4-Dimethylamino-pyridin, N- Methyl-piperidin, l,4-Diazabicyclo[2.2.2]-octan (DABCO), 1,5-Diazabicyclo[4.3.0]- non-5-en (DBN), oder l,8-Diazabicyclo[5.4.0]-undec-7-en (DBU).The processes (a) and (b) according to the invention for the preparation of the compounds of the general formula (I) are each preferably carried out using a reaction aid. The usual inorganic or organic bases or acid acceptors are generally suitable as reaction aids for the processes according to the invention preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as, for example, 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 -l-propanolate, -n- -l-, -s- or -t-butanolate, also also basic organic nitrogen compounds such as Tπmet hylamine, triethylamine, tπpropylamine, tnbutylamm, Ethvl-dnsopropvlamm, N, N-Dιmethyl-cvclohexylamιn, Dicvclohexylamm, Ethyl-dicyclohexylamm, NN-Dimethyl-anihn, N, N-Dπnethyl-Pyπdindin, 2-,

1-4 Methvl-, 2,4-Dιmeth \ l 2 6-Dιmethvl-, 3,4-Dιmethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, 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).

The inventive methods for the preparation of the compounds of all. my formula (I) are each preferably carried out using a diluent. In addition to water, the most suitable diluents are 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; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide,

N-methyl-pyrrolidone or hexamethylphosphoric 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 water.

The reaction temperatures can be varied over a wide range in carrying out processes (a) and (b) according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.

Processes (a) and (b) 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 processes (a) and (b) according to the invention, the starting materials are generally used in approximately equimolar 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 generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (cf. the production examples).

According to the invention, all plants and parts of plants can be treated. Under

Plants are understood to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants), and their populations and mixed populations. Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or cannot be protected by plant breeders' rights, and the populations and mixed populations of these plants. Plant parts are to be understood to mean all above-ground and underground plant parts and plant organs, such as sprout, leaf, flower and root, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes. The plant parts also include vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.

The treatment of the plants and parts of plants according to the invention is carried out by the customary treatment methods, for example by dipping, spraying, evaporating, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by enveloping. 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 all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount p used

The active compounds according to the invention can e.g. can be used in the following plants:

Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda,

Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochidium, Lamium, Lamium, Lammium 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.

Dicotyledon cultures of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon,

Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochlo

Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium. Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Sci us, Setaria, Sorghum.

Monocot cultures of the genera: Allium, Pineapple, Asparagus, Avena, Hordeum,

Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticaiε, Triticum, Zea. 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

The novel active compounds are suitable, depending on dei ^Jr concentration to Totalunkrautbekampfüng, eg on Industπe- and rail tracks, and on paths and areas with or without tree plantings Likewise, the inventive agents for controlling weeds in perennial crops, for example forests, decorative woodworking, fruit -, Wine, citrus, nut, banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture flats as well as for selective weed control in sustainable crops be used

The compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process

The active ingredients can be converted into the usual formulations, such as

Solutions, emulsions, powdered powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as very fine encapsulations in polymeric substances

These formulations are prepared in a known manner, for example by mixing the substances with extenders, that is to say liquid solvents and / or solid carriers, if appropriate 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 solvents can, for example, also be used as auxiliary solvents. Liquid solvents are essentially suitable. Aromatics, such as xylene, toluene, or alkyl naphthahn, chlorinated aromatics and chlorinated ahphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chlorides, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and the like Ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

Solid carrier materials are suitable: for example, ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules Question: e.g. broken and fractionated natural rocks such as calcite,

Marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifying and / or foam-generating agents come m question: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol

Ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite leaching 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 also natural phosphophides, such as wafers and lecithins and synthetic phosphohpides, can be used in the formulations. Other additives can be mineral and vegetable oils Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be 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 in a mixture with known herbicides for weed control, 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, amidosulfüron, anilofos, asulam, atrazine, azafenidin,

Azimsulfuron, Beflubutamide, Benazolin (-ethyl), Benfuresate, Bensulfuron (-methyl), Bentazon, Benzfendizone, Benzobicyclon, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromyniloxime, Bromofenoxim, Butachlor, Butafenacil, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (- ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinidon (-ethyl), Cinmoxurin, Clefoximethyl, Cinmoximethyl, Cinmoxurin Clethodim, Clodinafop (-propargyl), Clomazone, Clome-prop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulam (-methyl), Cumyluron, Cyanazine, Cybutryne, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl) D, 2,4-DB, 2,4-DP, desmedipham, dialates, dicamba, diclofop (-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Diitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epropodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Ethoxysulfuron, Etobenzanid, Fenoxaprop (-P-ethyl), Fentrazamide, Flamprop (-isopropyl), Flamprop (-isopropyl-L). Flamprop (methyl), flazasulfuron, florasulam, Fluazifop (-P-butyl), Fluazolate, Flucarbazone (-sodium), Flufenacet, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumetsulam, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxsulfam, Flupropilamur (Flupropilamur) , -sodium), flurenol (-butyl), fluridone, fluroxypyr (-meptyl), flurprimidol, flurtamone, fluthiacet (-methyl), fluthiamide, fomesafen, glufosinate (-ammoniα :: - ¹ "

Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl), Haloxyfop- (-P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Iazosulfuron, Iazosulfuron, -sodium), Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxa- flutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Mesotione, Metamitron, Metazachlor, Metobenzomethonuron (alpha-) metolachlor, metosulam, metoxuron, metribuzin, metsulfuron (- methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfyonef, oxasulfuron, oxasulfuron, Paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone, pethoxamide, phenmedipham, picolinafen, piperophos, pretilachlor, primisulfuron (-methyl), procarbazone (-sodium), prometryn, propachlor, propanil, propa- quizafop, propisochlor, propyzamide P rosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazolate, pyrazosulfüron (-ethyl), pyrazoxyfen, pyribenzoxime, pyributicarb, pyridate, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac, quinmerac,

Quinoclamine, Quizalofop (-P-ethyl), Quizalofop (-P-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthoxylazine, Teprutoxyl Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thifensulfuron (- methyl), Thiobencarb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron-

(-methyl), triclopyr, tridiphane, trifluralin and triflusulfuron, tritosulfuron.

A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also 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. They are used in the customary manner, for example by watering, spraying, spraying or scattering.

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

The amount of active ingredient used can vary over a wide range. It essentially depends 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.

Preparation Examples:

example 1

A solution of 2.5 g (8.3 mmol) of 2- (3-trifluoromethyl-phenoxy) -nicotinic acid chloride in 30 ml of toluene is stirred at room temperature (approx. 20 ° C.) to a mixture of 1.0 g (7.0 mmol) 4-chloro-2-methyl-aniline, 0.71 g (7.0 mmol) triethylamine and 60 ml toluene added dropwise. The reaction mixture is stirred for 15 hours at room temperature, then diluted to about twice the volume with toluene, washed successively with 5% aqueous hydrochloric acid, with 5% sodium hydroxide solution and with water, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue is digested with petroleum ether and the crystalline product is isolated by suction.

2.5 g (88% of theory) of N- (4-chloro-2-methylphenyl) -2- (3-trifluoromethylphenoxy) -3-pyridine-carboxamide with a melting point of 161 ° C. are obtained.

Analogously to Example 1 and in accordance with the general description of the production process according to the invention, it is also possible, for example, to prepare the compounds of the general formula (I) listed in Table 1 below.

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

R stands for hydrogen in all cases

The logP value given in Table 1 was determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C. Eluents for determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.

The calibration was carried out using unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones).

The lambda max values were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals. Starting materials of the formula (III): Example (III- 1)

182.5 g (1.64 mol) of 4-fluoro-aniline are added dropwise at room temperature (about 20.degree. C.) with stirring to a solution of 208 g (2.31 mol) of diethyl sulfide in 2.7 l of chloroform. Then 307 g (2.3 mol) of N-chlorosuccinimide are added in portions at 15 ° C. to 20 ° C. within about 25 minutes and then 318 ml (2.3 mol) of triethylamine are added dropwise within about 15 minutes , The mixture is then stirred for a further 15 minutes at 15 ° C. to 20 ° C. and then heated under reflux for 12 hours. After cooling to room temperature, it is washed twice with 500 ml of 2N sodium hydroxide solution, dried with magnesium sulfate and filtered. The filtrate is concentrated in a water jet vacuum and the oily residue is purified by distillation under reduced pressure.

198 g (61% of theory) of 2- (l-ethylthio-ethyl) -4-fluoro-aniline with a boiling point of 115 ° C. (at 1 mbar) are obtained.

Example (III-2)

15 g (70 mmol) of 2- (l-ethylthioethyl) -4-chloroaniline and 12 g of Raney nickel in nitrogen in 100 ml of ethanol are placed in an autoclave (300 ml, V4A steel). After closing, the autoclave is "flushed" three times with hydrogen - d. H. Press hydrogen three times up to 5 bar and relax three times again - and then press hydrogen up to a pressure of 50 bar. The mixture is heated to 150 ° C. in the course of an hour (pressure rises to 70 bar). The mixture is then stirred for 4 hours at 100 bar hydrogen pressure and 150 ° C internal temperature. After cooling to room temperature, the autoclave is depressurized, the contents are rinsed out with ethanol and the catalyst is separated off by filtration. The filtrate is concentrated in a water jet vacuum and the oily residue is purified by distillation under reduced pressure.

7.5 g (69% of theory) of 4-chloro-2-ethyl-aniline with a boiling point of 102 ° C. are obtained

(at 1 mbar).

Analogously to Examples (III-1) or (III-2), it is also possible, for example, to prepare the compounds of the general formula (III) listed in Table 2 below.

Table 2: Examples of the compounds of the formula (III)

The compounds listed above in Table 2 as examples (III-7), (III-8) and (III-9) are not yet known from the literature; as new substances, they are also the subject of the present application. Le A 34 0 "\ usland

42

Application examples:

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 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area. The active ingredient concentration in the spray liquor is chosen so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.

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

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

In this test, for example, the compounds according to Preparation Example 1, 2, 3, 27, 28, 29, 31, 32, 37, 38, 39, 40, 41, 42, 44, 45, 46, 47 and 49 show with partly good compatibility against crops such as barley, maize, soy and wheat, strong action against weeds. 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, 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 level

Concentration.

Test plants with a height of 5 to 15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area. The concentration of the spray liquor is chosen so that in

1000 1 water / ha the desired amounts of active ingredient are applied.

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

It means:

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

In this test, for example, the compounds according to Preparation Example 2, 3, 4, 6, 7, 8, 18, 19, 26, 27, 28, 29, 30, 31, 32, 41, 44, 45, 46 and 47 show partially good tolerance to cultivated plants, such as Wheat, effective against weeds.

Claims

claims Substituted N-phenyl-phenoxynicotinic acid (thio) amides of the general formula (I)

in which represents O (oxygen) or S (sulfur), R represents hydrogen or alkyl which is optionally substituted, Is alkenyl or alkynyl, R represents hydrogen, halogen or optionally substituted alkyl, R ^{3 represents} cyano, halogen, SF ₅ , or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, R represents hydrogen, cyano, halogen, or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, R represents nitro, cyano, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, and - if R is different from hydrogen - also represents hydrogen, R ^{6 represents} hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, and R ^{7 represents} hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, with the proviso that R> 6 is not halogen or methyl when R ^{5 is} methyl and R ² or R ^{7 is} hydrogen, and with the proviso that R is not hydrogen when R ³ and R ^{7 are} halogen and R ^{2 is} hydrogen. Compounds according to claim 1, characterized in that R ¹ for hydrogen, for optionally by cyano, halogen, dC ₄ - Alkoxy, C ₁ -C ₄ -alkylthio, C, -C ₄ -alkylsulfinyl or CC ₄ - alkylsulfonyl-substituted alkyl having 1 to 5 carbon atoms, or represents in each case optionally substituted by cyano or halogen-substituted alkenyl or alkynyl each having 3 to 5 carbon atoms, R ^{2 represents} hydrogen, halogen or alkyl which has 1 to 5 carbon atoms and is optionally substituted by cyano, halogen or -CC alkoxy, R ^{3 represents} cyano, halogen, SF ₅ , or alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 5 carbon atoms each optionally substituted by cyano, halogen or C 1 -C ₄ -alkoxy, R ^{4 represents} hydrogen, cyano, halogen, or alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 5 carbon atoms each optionally substituted by cyano, halogen or C 1 -C 6 -alkoxy, R ⁵ for nitro, cyano, carbamoyl, thiocarbamoyl, halogen, or for alkyl optionally substituted by cyano, halogen, C1-C4-alkoxy, C ₁ -C ₄ -alkylthio, -C-C ₄ - alkylsulfinyl or C1-C4-alkylsulfonyl 1 to 5 carbon atoms, and - in the event that R ^! is different from hydrogen - also stands for hydrogen, R ⁶ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, halogen, or for alkyl optionally substituted by cyano, halogen, -C-C - alkoxy, C ₁ -G - alkylthio, -C-C - alkylsulfinyl or dC - alkylsulfonyl 1 to 5 carbon atoms, and R ⁷ for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, halogen, or for alkyl optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C 4 alkylsulfinyl or dC - alkylsulfonyl with 1 to 5 carbon atoms. 3. Compounds according to claim 1, characterized in that R ¹ for hydrogen, each optionally by cyano, fluorine, chlorine, methoxy or ethoxy, methylthio or ethylthio, methylsulfinyl or Ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or for propenyl, butenyl, propynyl or butynyl which are optionally substituted by cyano, fluorine, chlorine or bromine stands, R ^{2 represents} hydrogen, fluorine, chlorine, bromine, or in each case methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, R ³ for cyano, fluorine, chlorine, bromine, SF ₅ , or for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, R ^{4 represents} hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, Ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, R ⁵ for nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, fluorine, chlorine, methoxy, Ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl substituted methyl, ethyl, n- or i -Propyl, and - in the event that R ^{1 is} different from hydrogen - also stands for hydrogen, R ° for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, Chlorine, bromine, or for optionally by cyano, fluorine, chlorine, Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, Methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl substituted methyl, ethyl, n- or i-propyl, and R 'for hydrogen, nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio , Methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl substituted methyl, ethyl, n- or i-propyl. 4. Compounds according to claim 1, characterized in that R ¹ for hydrogen, each optionally by cyano, fluorine, chlorine, Methoxy or ethoxy substituted methyl or ethyl, or represents propenyl or propynyl optionally substituted by fluorine or chlorine, , 1 R "stands for hydrogen, fluorine, chlorine, bromine, or for methyl or ethyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, R ^{3 represents} cyano, fluorine, chlorine, bromine, or methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, R ^{4 stands} for cyano, fluorine, chlorine, bromine, or for methyl, ethyl, methoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy. R ⁵ for cyano, fluorine, chlorine, bromine, or for methyl or ethyl substituted in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, and - in the event that R ¹ is different from hydrogen - also stands for hydrogen, R ^{6 stands} for hydrogen, nitro, cyano, fluorine, chlorine, bromine, or for methyl or ethyl substituted in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, and R ^{7 represents} hydrogen, cyano, fluorine, chlorine, bromine, or represents methyl or ethyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl. 5. A method for producing the compounds according to any one of claims 1 to 4, characterized in that (a) Phenoxynicotinic acid derivatives of the general formula (II)

in which Q, R ² , R ³ and R ^{4 have} the meaning given in one of claims 1 to 4 and Y represents halogen, imidazolyl, alkoxy, aryloxy or aralkoxy, - or corresponding carboxylic anhydrides - with aniline derivatives of the general formula (III)

in which R ¹ , R \ R ⁶ and R ^{7 have} the meaning given in one of claims 1 to 4, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or that one (b) Nicotinic acid derivatives of the general formula (IV)

in which Q, R ¹ , R ² , R ⁵ , R ⁶ and R ^{7 have} the meaning given in one of claims 1 to 4 and X represents halogen, with substituted phenols of the general formula (V)

in which R and R have the meaning given in one of claims 1 to 4, or with alkali metal salts of the compounds of formula (V) - if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of diluent, and, if appropriate, then subsequently converting the compounds of the general formula (I) thus obtained into other compounds of the general formula (I) within the scope of the definition of substituents by customary methods. 6. Aniline derivatives of the general formula (purple)

in which R ¹ , R ⁶ and R ^{7 have} the meaning given in one of claims 1 to 4, R ^{8 represents} -C ₃ alkyl (especially methyl or ethyl) and R ⁹ represents C 1 -C ₄ -alkyl (in particular methyl, ethyl, n- or i-propyl), except 4-chloro-2- (2-methylthio-ethyl) aniline. 7. Composition, characterized by a content of at least one compound according to one of claims 1 to 4 and conventional extenders. 8. Use of at least one compound according to one of the claims 1 to 4 to control unwanted plants.