WO2000031066A1

WO2000031066A1 - Substituted n-pyrazolyl-phenoxynicotinic acid-(thio)amides that can be used as herbicides

Info

Publication number: WO2000031066A1
Application number: PCT/EP1999/008659
Authority: WO
Inventors: Karl-Heinz Linker; Klaus-Helmut Müller; Mark Wilhelm Drewes; Dieter Feucht; Rolf Pontzen; Ingo Wetcholowsky
Original assignee: Bayer Aktiengesellschaft
Priority date: 1998-11-24
Filing date: 1999-11-11
Publication date: 2000-06-02
Also published as: AU1382400A; DE19854081A1

Abstract

The invention relates to novel substituted N-pyrazolyl-phenoxynicotinic acid-(thio)amides of general formula (I) wherein n represents 0, 1, or 2, Q represents O (oxygen) or S (sulphur), R1 represents hydrogen or respectively, optionally substituted alkyl, alkenyl or alkinyl, R2 stands for hydrogen or for respectively, optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl or phenyl, R3 stands for hydroxy, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for respectively, optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, or when n is 2 and two radicals R3 are bonded to adjacent ring atoms also represents alkandiyl (alkylene) together with a second radical R3, R4 represents hydrogen, cyano, halogen or represents respectively, optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl, R5 stands for cyano, halogen, SF¿5? represents respectively, optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulphonyl, R?6¿ represents hydrogen, cyano, halogen or respectively, optionally alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl and R7 stands for hydrogen, halogen or optionally substituted alkyl. The invention also relates to a method for the production and use thereof as herbicides.

Description

SUBSTITUTED N-PYRAZOLYL-PHENOXYNICONIC ACID (THIO) AMIDES, USEFUL AS HERBICIDES

The invention relates to new substituted N-pyrazolylphenoxynicotinsäure- (thio) - amides. Process 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-53011; Pestic. Sci. 18 (1987), 15-28). Substituted N-pyrazolyl-phenoxynicotinsäure- (thio) amides, however, are not yet known from the literature.

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

in which

n stands for the numbers 0, 1 or 2,

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

R ^{1 represents} hydrogen or represents optionally substituted alkyl, alkenyl or alkynyl, R ^{2 represents} hydrogen or optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl or phenyl,

R ³ for hydroxyl, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkoxy,

Alkoxycarbonyl, alkylthio. Alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, or - if n stands for 2 and two radicals R ³ are bonded to adjacent ring atoms - also to - together with a second radical R ^{3 represents} alkanediyl (alkylene),

R ^{4 represents} hydrogen, cyano, halogen, or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl,

R ⁵ for cyano, halogen, SF ₅ , or for optionally optionally substituted alkyl,

Alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl,

R ^{6 represents} hydrogen, cyano, halogen, or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, and

R ^{7 represents} hydrogen, halogen or optionally substituted alkyl,

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 of the radicals listed in the formulas mentioned here are explained below.

Q is preferably 0 (oxygen). R ¹ preferably represents hydrogen, alkyl with 1 to 6 carbon atoms optionally substituted by cyano, halogen or C 1 -C ₄ -alkoxy, or alkenyl or alkynyl each optionally substituted by cyano or halogen, each having 2 to 6 carbon atoms.

R ² preferably represents hydrogen, alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, halogen or C 1 -C ₄ -alkoxy, each represents alkenyl or alkynyl which has 2 to 6 carbon atoms and is optionally substituted by cyano or halogen, and each optionally through cyano. Halogen or C, -C ₄ alkyl substituted cycloalkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, or for optionally by nitro, cyano, halogen, C, -C ₄ alkyl, C , -C ₄ haloalkyl, C, -C ₄ alkoxy, C, -C ₄ haloalkoxy or C, -C ₄ alkoxy-carbonyl substituted

Phenyl.

R ³ preferably stands for hydroxy, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, for alkyl, alkoxy, alkoxycarbonyl, alkylthio, which are each optionally substituted by cyano, halogen or C _r C ₄ alkoxy,

Alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl groups, for alkenyl or alkynyl or alkynyl, each optionally substituted by cyano or halogen, each having, if appropriate, cyano, halogen or C 1 -C ₄ -alkyl substituted cycloalkyl or cycloalkylalkyl, each with 3 to 6

Carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally by nitro, cyano, halogen, C, -C ₄ alkyl, C, -C ₄ haloalkyl, C _r C ₄ alkoxy, C, -C ₄ - haloalkoxy or C, -C ₄ -alkoxy-carbonyl-substituted aryl or aryl-alkyl each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, or for optionally substituted by nitro, cyano, halogen, C, -C ₄ alkyl, C, -C ₄ haloalkyl, C, -C ₄ alkoxy, C, -C ₄ haloalkoxy or C, -C ₄ alkoxycarbonyl Heterocyclyl or heterocyclylalkyl from the series furyl, furyl-C _r C ₄ -alkyl, thienyl, thienyl-C, -C ₄ -alkyl, pyrazolyl, pyrazolyl-C, -C ₄ -alkyl, pyridiyl, pyridyl-C, -C ₄ -alkyl, pyrimidyl, pyrimidyl-C, -C ₄ -alkyl, or - in the event that n is 2 and two radicals R ³ are bonded to adjacent ring atoms - also together with a second radical R ³ for alkanediyl (alkylene) with 3 to 5 carbon atoms.

R ⁴ preferably represents hydrogen, cyano, halogen, or alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 4 carbon atoms each optionally substituted by cyano, halogen or C 1 -C ₄ -alkoxy.

R ³ preferably represents cyano, halogen, SF ₅ , or alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 4 carbon atoms each optionally substituted by cyano, halogen or C _r C ₄ alkoxy.

R ⁶ preferably represents hydrogen, cyano, halogen, or alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, each having 1 to 4 carbon atoms, optionally substituted by cyano, halogen or C, -C ₄ -alkoxy.

R ⁷ preferably represents hydrogen, halogen or optionally by cyano,

Halogen or C, -C ₄ alkoxy substituted alkyl having 1 to 4 carbon atoms.

R ¹ particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl, n- or i-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or in each case optionally by cyano, Fluorine, chlorine or bromine substituted propenyl, butenyl, propynyl or butynyl.

R ² particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl, n-, i- or s-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, each in each case optionally by cyano, fluorine , Chlorine or bromine substituted propenyl, butenyl, propynyl or butynyl, each optionally substituted by cyano, fluorine, chlorine. Bromine, methyl, ethyl, n- or i-propyl substituted cyclopropyl, cyclobutyl. Cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutyimethyl, cyclopentylmethyl or

Cyclohexylmethyl, or for optionally by nitro, cyano. Fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxy carbonyl, Ethoxycarbonyl, n- or i-propoxy-carbonyl substituted phenyl.

R ³ particularly preferably represents hydroxy, amino, nitro. Cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine. Chlorine, bromine, for each methyl, ethyl, n- or i-propyl, n-, i- substituted by cyano, fluorine, chlorine, methoxy or ethoxy. s- or t-butyl, methoxy, ethoxy. n- or i-

Propoxy, methoxy carbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino , Ethylamino, n- or i-propylamino, dimethylamino or diethylamino, for each optionally by cyano. Fluorine, chlorine or bromine-substituted propenyl, butenyl, propynyl or butynyl, each for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutyimethyl, cyclopentylmethyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl or cyclohexylmethyl, each optionally with nitro, cyano, fluorine,

Chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoro- methyl. Methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy. Methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl substituted phenyl or benzyl, or - if n stands for 2 and two radicals R ³ are bonded to adjacent ring atoms - also together with a second radical R ³ for Dimethylene (ethane-1,2-diyl) or trimethylene (propane-1,3-diyl).

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. Methylsulfmyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl.

R ^ particularly preferably represents cyano, fluorine. Chlorine, bromine, SF ₅ , or for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy,, methylthio, ethylthio, each optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy , n- or i-Propylthio, methylsulfmyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl.

R ⁶ 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, methylsulfmyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl.

R ⁷ particularly preferably represents hydrogen, fluorine, chlorine, bromine or optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy

Methyl, ethyl, n- or i-propyl. R ¹ very particularly preferably represents hydrogen.

R ² very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyanomethyl, cyanoethyl, cyanopropyl,

Propenyl, butenyl, propynyl, butynyl, cyclopropyl or phenyl.

R ³ very particularly preferably represents nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyanomethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy , Methoxy carbonyl, ethoxycarbonyl or

Cyclopropyl.

R ⁴ very particularly preferably represents hydrogen or fluorine.

R ⁵ very particularly preferably represents cyano, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy.

R ⁶ very particularly preferably represents hydrogen or fluorine.

R ⁷ very particularly preferably represents hydrogen or methyl.

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 there is a combination of the meanings listed above as being particularly preferred.

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

Meanings exist. In particular, compounds of the formula (IA), (IB) or (IC) are emphasized

in which

n represents the numbers 0, 1 or 2,

Q stands for O (oxygen),

R ^{1 represents} hydrogen,

R ^{2 represents} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,

Cyanomethyl, cyanoethyl, cyanopropyl, propenyl, butenyl. Propinyl, butinyl, cyclopropyl or phenyl,

R ³ for nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyanomethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methoxycarbonyl, ethoxycarbonyl or cyclopropyl,

R ^{4 represents} hydrogen or fluorine,

R ⁵ for cyano, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy or

Trifluoromethoxy stands,

R ^{6 represents} hydrogen or fluorine, and

R ^{7 represents} hydrogen or methyl.

Examples of the compounds of the general formula (I) according to the invention are listed in the groups below. Group 1

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in the following table:

- 1 year -

Group 2

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1.

Group 3

Q, R ¹ , R ⁴ , R \ R ⁶ and R ⁷ have, for example, the meanings listed in Group 1.

Group 4

Q, R ¹ , R ⁴ , R ', R ⁶ and R ⁷ have, for example, the meanings listed in Group 1.

Group 5

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, those listed in Group 1

Meanings. Group 6

Meanings.

Group 7

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 8

Meanings.

Group 9

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 10

Q, R ¹ . R ⁴ , R \ R ⁶ and R ⁷ have, for example, those listed in Group 1

Meanings.

Group 11

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 12

Meanings.

Group 13

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 14

Meanings.

Group 15

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 16

Meanings.

Group 17

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 18

Meanings.

Group 19

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 20

Q, R ¹ , R \ R \ R ⁶ and R ⁷ have, for example, those listed in Group 1

Meanings.

Group 21

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 22

Q, R ^! , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, those listed in Group 1

Meanings.

Group 23

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 24

Q, R ¹ , R ⁴ , R \ R ⁶ and R ⁷ have, for example, those listed in Group 1

Meanings.

Group 25

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 26

Meanings.

Group 27

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 28

Meanings.

Group 29

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 30

Meanings.

Group 31

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 32

.

Q, R ¹ , R ⁴ . R ³ , R ⁶ and R ⁷ have, for example, those listed in Group 1

Meanings.

Group 33

Q, R ¹ . R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 34

Meanings.

Group 35

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 36

Q, R ^! , R ⁴ , R ³ , R ⁶ and R ⁷ have, for example, those listed in Group 1

Meanings.

Group 37

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 38

Q, R ¹ , R ⁴ , R ³ , R ⁶ and R ⁷ have, for example, those listed in Group 1

Meanings.

Group 39

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 40

Meanings.

Group 41

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 42

Meanings.

Group 43

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 44

Meanings.

Group 45

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 46

Meanings.

Group 47

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 48

Q, R ¹ , R ⁴ , R ^s , R ⁶ and R ⁷ have, for example, those listed in Group 1

Meanings.

Group 49

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 50

Meanings.

Group 51

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 52

Q, R ¹ , R ⁴ , R ³ . R ⁶ and R ⁷ have, for example, those listed in Group 1

Meanings.

Group 53

Q, R ¹ , R ⁴ , R ³ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 54

Meanings.

Group 55

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 56

Meanings.

Group 57

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 58

Meanings.

Group 59

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 60

Meanings.

Group 61

Q, R ¹ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have, for example, the meanings listed in Group 1. Group 62

Meanings.

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. This

Residual definitions can be combined with one another, i.e. also between the specified preferred ranges.

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

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

(a) aminopyrazoles of the general formula (II)

in which

n, R ¹ , R ² and R ^{3 have} the meaning given above,

with carboxylic acid derivatives of the general formula (III)

in which

Q, R ⁴ , R ⁵ , R ⁶ and R ^{7 have} the meaning given above and

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

- or with corresponding carboxylic anhydrides -

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

or if you (b) N-pyrazolyl nicotinic acid amides of the general formula (IV)

in which

n, R ¹ , R ² , R ³ and R ^{7 have} the meaning given above, and

X represents halogen,

with phenols of the general formula (V)

in which

R ⁴ , R ⁵ and R ^{6 have} the meaning given above,

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

If, for example, 3-amino-l, 5-dimethyl-pyrazole and 2- (3-chlorophenoxy) -5-methyl-nicotinoyl chloride are used as starting materials, the course of the reaction in process (a) according to the invention can be outlined using the following formula:

If, for example, N- (1-methyl-pyrazol-4-yl) -2,5-difluoro-nicotinic acid amide and 3-cyano-phenol are used as starting materials, the course of 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 aminopyrazoles 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), n, R ¹ , R ² and R ³ preferably have those meanings which are preferred, particularly preferred or very particularly preferred for n in connection with the description of the compounds of the general formula (I) according to the invention , R ¹ , R ² and R ^{3 have been} specified. The starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. WO-A-94/08999, WO-A-9806702, J. Am. Chem. Soc. 81 (1959) , 2456-2464).

Formula (III) provides a general definition of the carboxylic acid derivatives to be used further as starting materials in process (a) according to the invention. In the general formula (III), Q, R ⁴ , R ⁵ , R ⁶ and R ⁷ preferably have those meanings which are preferred, particularly preferred or very particular in connection with the description of the compounds of the general formula (I) according to the invention have preferably been given for Q, R ⁴ , R ⁵ , R ⁶ and R ⁷ ; Y preferably represents fluorine, chlorine, bromine, imidazolyl, methoxy, ethoxy, phenoxy or benzyloxy, in particular chlorine.

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

(1975), 1-8).

Formula (IV) provides a general definition of the N-pyrazolyl nicotinic acid amides to be used as starting materials in process (b) according to the invention for the preparation of compounds of the general formula (I). In general

Formula (IV) n, R ¹ , R ² , R ³ and R ⁷ preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the general formula (I) according to the invention as preferred, particularly preferred or very particularly preferred for n , R ¹ , R ² , R ³ and R ^{7 have been} given; X preferably represents fluorine, chlorine or bromine, in particular fluorine or chlorine.

The starting materials of the general formula (IV) are not yet known from the literature. The compounds of the general formula (IV) are obtained in a manner known per se if nicotinic acid derivatives of the general formula (VI)

in which

Q, R ⁷ , X and Y have the meaning given above

with aminopyrazoles of the general formula (II) - above - optionally in the presence of a reaction auxiliary, such as e.g. Triethylamine or potassium carbonate, optionally in the presence of a diluent, e.g. Acetone, acetonitrile or toluene, at temperatures between 0 ° C and 150 ° C.

Formula (V) provides a general definition of the phenols to be used as starting materials in process (b) according to the invention. In the general formula (V), R ⁴ , R ⁵ and R ⁶ preferably have those meanings which are preferred, particularly preferred or very particularly preferred for R already in connection with the description of the compounds of the general formula (I) according to the invention ⁴ , R ⁵ and R ^{6 have been} specified.

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

The processes according to the invention for the preparation of the compounds of the general formula (I) are preferably carried out using diluents. Suitable diluents for carrying out processes (a) and (b) according to the invention are, in addition to water, 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; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethyl-phosphoric 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.

Suitable reaction auxiliaries for processes (a) and (b) 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, 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; also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, 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-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).

Phase transfer catalysts are also suitable as further reaction aids for processes (a) and (b) according to the invention. Examples of such catalysts are: Tetrabutylammonium bromide. Tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogen sulfate, methyl trioctylammonium chloride, hexadecyl trimethylammonium chloride, hexadecyl trimethylammonium bromide, benzyl trimethylammonium chloride, benzyl triethylammonium benzyl triethylammonium Benzyl triethylammonium hydroxide, benzyl tributyl ammonium chloride, benzyl tributylammonium bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tributyl hexadecylphosphonium bromide, butyl triphenylphosphonium tetronyl tetromethyl tetronyl tetromethyl tetromethyl tetromethyl bromide.

The reaction temperatures can be varied within a substantial range when 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.

The processes 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 for several hours at the required temperature. Working up is carried out according to customary methods (cf. 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 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 used.

The active compounds according to the invention can e.g. can be used 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. Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

Dicot 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. Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Aegilops, Phalaris.

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, in particular also to transgenic plants. Depending on the concentration, the active compounds according to the invention are suitable for combating total weeds, for example on industrial and rail tracks and on paths and squares with and without tree growth. The active compounds according to the invention for combating weeds in permanent crops, for example forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm,

Cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land as well as for selective weed control in annual crops.

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 compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.

These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as an extender, e.g. also organic

Solvents are used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic 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 isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

Possible solid carriers are: e.g. 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: 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 stems; as emulsifying and / or foam-generating agents are possible: 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 liquor and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids 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 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, Anilofos, Asulam, Atrazine. Azafenidin, Azimsulfuron, Benazolin (-ethyl), Benfuresate, Bensulfuron (-methyl), Bentazon, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylates, Cafenstrole, Caloxydim, Carbetamides, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben,

Chloridazon, Chlorimuron (-ethyl), Chloronitrofen, Chlorsulfuron, Chlortoluron, Cinidon (-ethyl), Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-mulam) ), Cumyluron, Cyanazines, Cybutryne, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP. Desmedipham, Diallate, Dicamba,

Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Difluefenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Epithonium, Dithiopyran EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Ethoxysulfuron, Etobenzanid, Fenoxaprop (-P-ethyl), Flamprop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (-methyl), Flazasulfuron, Fluazifop (-P-butyl), Fluazolate, Flucarbazone, Flufenacet, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumetsulam, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupacoxil, Flupacoxil, Flupetsilam methyl, -sodium), flurenol (-butyl), fluridone, fluroxypyr (-meptyl), flurprimidol, flurtamone, fluothiacet (-methyl), fluthiamide, fomesafen, glufosinate (-ammonium), glyphosate (- isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl), Haloxyfop (-P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Iodosulfilon, Isoxynulfuron, Isodynosulfuron, Isodosulfuron, Isoxynulfonon , Isouron, Isoxaben, Isoxachlortole, Isoxaflutole. Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Mesotrione, Metamitron,

Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolechlor, Metosulam, Metoxuron, Metribuzin, Metsulftιron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Orben- carburon, Norflurazon Oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone. Oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pentoxazone, phenmedipham. Piperophos,

Pretilachlor, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil. Propaquizafop, Propisochlor, Propyzamide, Prosulfocarb, Prosulfuron, Pyraflufen (-ethyl), Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyfen, Pyribenzoxim, Pyributicarb, Pyridate, Pyriminobac (-methyl), Pyrithiobac (-sac), Quith 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.

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.

MANUFACTURING EXAMPLES:

example 1

0.8 g (7.5 mmol) l, 3-dimethyl-5-aminopyrazole and 0.83 g (8.2 mmol) triethylamine are placed in 80 ml toluene, at 25 ° C with 2.26 g (7.5 mmol) of 2- (3-trifluoromethylphenoxy) nicotinic acid chloride are added and the mixture is stirred at 25 ° C. for 12 hours. The mixture is then mixed with 2N hydrochloric acid, the organic phase is separated off, washed with water, dried over sodium sulfate and concentrated in a water jet vacuum.

1.4 g (50% of theory) of N- (1,3-dimethylpyrazol-5-yl) -2- (3-trifluoromethylphenoxy) nicotinamide of melting point 132 ° C. are obtained.

Example 2:

0.9 g (5 mmol) of 5-difluoromethoxy-3-amino-1,4-dimethyl-pyrazole in 100 ml of acetonitrile are mixed with 0.2 g (6 mmol) of sodium hydride (80% in paraffin), 30 minutes at room temperature ( 25 ° C), then 3 g (10 mmol) of 2- (3-trifluoromethyl-phenoxy) -nicotinic acid chloride were added and the mixture was stirred at room temperature for 12 hours. The mixture is concentrated, 2N hydrochloric acid is added, the organic phase is extracted with dichloromethane, washed with water, dried over sodium sulfate and concentrated in a water jet vacuum. For purification, chromatograph on silica gel using cyclohexane / ethyl acetate (vol .: 1: 1).

0.9 g (41% of theory) of N- (1,4-dimethyl-5-difluoromethoxy-pyrazol-3-yl) -2- (3-trifluoromethyl-phenoxy) nicotinic acid amide are obtained.

Η NMR (DMSO, δ): 1.85; 3.64; 8.25-8.27; 10.24 ppm. Analogously to Examples 1 and 2 and in accordance with the general description of the production processes according to the invention, the compounds of the formula (I) listed in the table below can also be prepared.

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

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 ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area. The concentration of 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 annihilation

In this test, for example, the compounds according to Preparation Examples 1, 10 and 13, with good tolerance to crop plants, such as barley and cotton, show a 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

Test plants with a height of 5 - 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.

It means:

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

In this test, for example, the compounds according to Preparation Examples 1 and 17 show good tolerance to crop plants, such as Wheat, effective against weeds.

Claims

claims

1. Substituted N-pyrazolyl-phenoxynicotinsäure- (thio) amides of the general

Formula (I)

in which

n stands for the numbers 0, 1 or 2,

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

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

R ^{2 represents} hydrogen or optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl or phenyl,

R ³ for hydroxy, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for each optionally substituted

Alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, or - in the event that n is 2 and two radicals R ³ on be - neighboring ring atoms are bonded - also together with a second radical R ^{J represents} alkanediyl (alkylene),

R ⁴ for hydrogen. Cyano, halogen, or represents optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl,

R ³ for cyano, halogen, SF ₅ , or for each optionally substituted alkyl, alkoxy, alkylthio. Alkylsulfinyl or alkylsulfonyl,

R ⁶ for hydrogen. Cyano, halogen, or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, and

R ^{7 represents} hydrogen, halogen or optionally substituted alkyl.

2. Substituted N-pyrazolyl-phenoxynicotinsäure- (thio) amides according to claim

1, in which

n stands for the numbers 0, 1 or 2,

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

R ^{1 is} hydrogen, optionally by cyano, halogen or C, -C

Alkoxy-substituted alkyl having 1 to 6 carbon atoms, or alkenyl or alkynyl each optionally substituted by cyano or halogen, each having 2 to 6 carbon atoms,

R ² for hydrogen, for optionally by cyano, halogen or C, -C ₄ -

Alkoxy substituted alkyl of 1 to 6 carbon atoms, for each alkenyl or alkynyl, optionally substituted by cyano or halogen, each having 2 to 6 carbon atoms, for cycloalkyl or cycloalkylalkyl, each optionally substituted by cyano, halogen or C _] -C ₄ -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the

Alkyl part, or for optionally by nitro, cyano, halogen, C _r C ₄ alkyl, C, -C ₄ haloalkyl, C, -C ₄ alkoxy, C, -C ₄ haloalkoxy or C, -C ₄ alkoxy -carbonyl substituted phenyl,

for hydroxy, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, for each optionally by cyano. Halogen or C, -C ₄ -alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by cyano or halogen

Alkenyl or alkynyl each having 2 to 6 carbon atoms, for each cycloalkyl or cycloalkylalkyl optionally substituted by cyano, halogen or C 1 -C ₄ -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part, each optionally by

Nitro, cyano, halogen, C, -C ₄ alkyl, C, -C ₄ haloalkyl, C, -C ₄ alkoxy, C, -C ₄ haloalkoxy or C _r C ₄ alkoxycarbonyl substituted aryl or arylalkyl each with 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by nitro, cyano,

Halogen, C, -C ₄ alkyl, C, -C ₄ haloalkyl, C, -C ₄ alkoxy, C, -C ₄ - haloalkoxy or C, -C ₄ -alkoxy-carbonyl substituted heterocyclyl or heterocyclylalkyl from the series Furyl, furyl-C _r C ₄ -alkyl, thienyl, thienyl-C, -C ₄ -alkyl, pyrazolyl, pyrazolyl-C, -C ₄ -alkyl, pyridiyl, pyridyl-C, -C ₄ -alkyl, pyrimidyl, pyrimidyl -C, -C ₄ alkyl, or - in the event that n is 2 and two radicals R ³ on adjacent Ring atoms are bonded - also together with a second radical R ^{3 represents} alkanediyl (alkylene) having 3 to 5 carbon atoms,

R ^{4 represents} hydrogen, cyano, halogen or alkyl which is optionally substituted by cyano, halogen or C 1 -C ₄ -alkoxy,

Alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 4 carbon atoms,

R ⁵ for cyano, halogen, SF ₅ , or for alkyl, alkoxy optionally substituted by cyano, halogen or C, -C ₄ -alkoxy,

Alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 4 carbon atoms,

R ^{6 represents} hydrogen, cyano, halogen or alkyl which is optionally substituted by cyano, halogen or C 1 -C ₄ -alkoxy,

Alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 4 carbon atoms, and

R ^{7 represents} hydrogen, halogen or alkyl which has 1 to 4 carbon atoms and is optionally substituted by cyano, halogen or C 1 -C ₄ -alkoxy.

3. Substituted N-pyrazolyl-phenoxynicotinsäure- (thio) amide according to claim 1, characterized in that

n stands for the numbers 0, 1 or 2,

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

R ¹ for hydrogen, each optionally by cyano, fluorine, chlorine,

Methoxy or ethoxy substituted methyl. Ethyl, n- or i-propyl, n- or i-butyl, or propenyl, butenyl, propynyl or butynyl which is optionally substituted by cyano, fluorine, chlorine or bromine,

R ² for hydrogen, for each optionally by cyano, fluorine, chlorine,

Methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, for propenyl, butenyl, propynyl or butinyl, each optionally substituted by cyano, fluorine, chlorine or bromine, for each optionally by cyano , Fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutyimethyl, cyclopentylmethyl or cyclohexylmethyl, or for optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i- Propoxy-carbonyl substituted phenyl,

R ³ for hydroxy, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, for each optionally through

Cyano, fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n - or i- propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfmyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl,

Ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino, for propenyl, butenyl, propynyl or butynyl optionally substituted by cyano, fluorine, chlorine or bromine, for each optionally substituted by cyano, Fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclo- propylmethyl, cyclobutyimethyl, cyclopentylmethyl or cyclohexylmethyl, for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, Ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl substituted phenyl or benzyl, or - in the event that n is 2 and two radicals R ^{3 are} bonded to adjacent ring atoms - also together with a second R ³ radical represents dimethylene (ethane-1,2-diyl) or trimethylene (propane-1,3-diyl),

R ⁴ for hydrogen, cyano, fluorine. Chlorine, bromine, or for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i- propoxy, methylthio, ethylthio, n- or i-, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy Propylthio, methylsulfmyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl,

R ⁵ for cyano, fluorine, chlorine. Bromine, SF ₅ , or for each optionally by cyano, fluorine, chlorine. Bromine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy,,

Methylthio, ethylthio, n- or i-propylthio, methylsulfmyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl,

R ⁶ for hydrogen, cyano, fluorine, chlorine, bromine, or for each optionally by cyano. Fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfmyl, ethylsulfinyl, n- or i- Propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, and R ^{7 represents} hydrogen, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy.

Substituted N-pyrazolyl-phenoxynicotinamide according to Claim 1, characterized by the formula (IA)

in which

n represents the numbers 0, 1 or 2,

Q stands for O (oxygen),

R ^{1 represents} hydrogen,

R ^{2 represents} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyanomethyl, cyanoethyl, cyanopropyl, propenyl, butenyl, propynyl, butinyl, cyclopropyl or phenyl,

R ³ for nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyanomethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methoxy carbonyl, Ethoxycarbonyl or cyclopropyl, R ^{4 represents} hydrogen or fluorine,

R ^{5 represents} cyano, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy,

R ^{6 represents} hydrogen or fluorine, and

R ^{7 represents} hydrogen or methyl.

5. Substituted N-pyrazolyl-phenoxynicotamides according to claim 1, characterized by the formula (IB)

in which

n represents the numbers 0, 1 or 2,

Q stands for O (oxygen),

R ^{1 represents} hydrogen, R ^{2 represents} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyanomethyl, cyanoethyl, cyanopropyl, propenyl, butenyl, propynyl, butinyl, cyclopropyl or phenyl,

R ^{3 represents} nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyanomethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or cyclopropyl,

R ^{4 represents} hydrogen or fluorine,

R ^{6 represents} hydrogen or fluorine, and

R ^{7 represents} hydrogen or methyl.

6. Substituted N-pyrazolylphenoxynicotineamides according to claim 1, characterized by the formula (IC)

in which

represents the numbers 0, 1 or 2, Q stands for O (oxygen),

R ^{1 represents} hydrogen,

Cyanomethyl, cyanoethyl, cyanopropyl, propenyl, butenyl, propynyl,

Butinyl, cyclopropyl or phenyl,

R ^{4 represents} hydrogen or fluorine,

R ^{6 represents} hydrogen or fluorine, and

R ^{7 represents} hydrogen or methyl.

7. Substituted N-pyrazolyl-phenoxynicotinsäure- (thio) amides according to any one of claims 1 to 6, characterized in that R ^{2 is} methyl.

8. Substituted N-pyrazolyl-phenoxynicotinsäure- (thio) amides according to any one of claims 1 to 7, characterized in that R ^{5 is} trifluoromethyl.

, Substituted N-pyrazolyl-phenoxynicotinsäure- (thio) amides according to any one of claims 1 to 8, characterized in that R ⁴ , R ⁶ and / or R ⁷ are (stands) for hydrogen.

10. A method for producing substituted N-pyrazolyl-phenoxynicotinic acid (thio) amides according to any one of claims 1 to 9, characterized in that

a) aminopyrazoles of the general formula (II)

in which

n, R ¹ , R ² and R ^{3 have} the meaning given in one of claims 1 to 7,

with carboxylic acid derivatives of the general formula (III)

in which Q, R ⁴ , R ⁵ , R ⁶ and R ^{7 have} the meaning given in one of Claims 1 to 6, 8 or 9 and

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

- or with corresponding carboxylic anhydrides -

or that one

b) N-pyrazolyl nicotinic acid amides of the general formula (IV)

in which

n, R ¹ , R ² , R ³ and R ^{7 have} the meaning given in one of claims 1 to 6, 8 or 9, and

X represents halogen,

with phenols of the general formula (V)

in which

R ⁴ , R ⁵ and R ^{6 have} the meaning given in one of claims 1 to 6, 8 or 9,

11. N-pyrazolyl nicotinic acid amides of the general formula (IV)

in which

n, R ¹ , R ² , R ³ and R ^{7 have} the meaning given in one of claims 1 to 7, and

X represents halogen.

12. A method for controlling unwanted plants, characterized in that at least one substituted N-pyrazolyl-phenoxynicotinic acid (thio) amide according to one of claims 1 to 9 is allowed to act on plants and / or their habitat.

13. Use of at least one substituted N-pyrazolyl-phenoxy-nicotinic acid (thio) amide according to one of claims 1 to 9 for controlling undesirable plants.

14. Herbicidal agents, characterized in that they contain at least one substituted N-pyrazolylphenoxynicotinic acid (thio) amide according to one of Claims 1 to 9.