EP0897385A1

EP0897385A1 - Herbicidal heterocyclically annulated benzoylisothiazoles

Info

Publication number: EP0897385A1
Application number: EP97918133A
Authority: EP
Inventors: Stefan Engel; Wolfgang Von Deyn; Regina Luise Hill; Uwe Kardorff; Martina Otten; Peter Plath; Marcus Vossen; Ulf Misslitz; Helmut Walter; Karl-Otto Westphalen
Original assignee: BASF SE
Current assignee: BASF SE
Priority date: 1996-04-16
Filing date: 1997-04-14
Publication date: 1999-02-24
Also published as: ZA973179B; CA2251657A1; AU2637797A; JP2000508330A; AR013306A1; WO1997038988A1; DE19614856A1; US5945381A

Abstract

4-benzoylisothiazoles have the general formula (1), in which the substituents have the following meanings: X stands for oxygen or sulphur; R1 stands for hydrogen, alkyl, alkenyl, alkinyl, optionally substituted alkoxycarbonyl, aryl, heterocyclyl or hetaryl; R2 stands for hydrogen, alkyl, alkenyl, alkinyl, cycloalkyl or cyclalkenyl, aryl, hetaryl or heterocyclyl; and R3 stands for a radical of general formulas (2a-d), in which n, A, B and the R?4, R5 and R6¿ substituents have the meanings given in claim 1. Also disclosed are the salts commonly used in agriculture of the 4-benzoylisothiazoles of general formula (1), a process for preparing the same and their use as herbicides.

Description

Herbicidal heterocyclically fused benzoylisothiazoles

description

The present invention relates to new substituted benzoylisothiazoles, processes for their preparation and their use as herbicides. From the patent literature (EP 0 527 036, EP 0 527 037, EP 0 560 482, EP 0 580 439, EP 0 588 357, EP 609 797, EP 0 609 798, EP 0 636 622, WO 94/14782, WO 94 / 18179, WO 95/15691 and WO 95/16678) it is known that substituted 4-benzoyl-5-cycloalkylisoxazoles represent a class of compounds with pronounced herbicidal activity in the pre-emergence process. 4- (2-Sulfonylmethyl-4-trifluoromethylbenzoyl) -5-cyclopropylisoxazole, a representative of this class of compounds is developed by Rh vonne-Poulenc as a herbicidal active ingredient against mono- and dicotyledonous harmful plants in the pre-emergence process in maize (RPA 201772, Technical Bulletin).

In addition, the herbicidal and insecticidal activity of substituted 4-alkyl- or 4-cycloalkyl-5-aryl- or 5-hetaryl-isoxazoles is known (GB 2 284 600, WO 95/22903, WO 95/22904 and WO 95 / 25105).

The herbicidal activity of the known compounds is only partially satisfactory in the case of inadequate activity in the post-emergence process, even in the pre-emergence process, if the crop plant tolerance is incomplete.

Herbicidal or insecticidal 4-benzoylisothiazoles according to the invention have hitherto not been found in the prior art.

So far, 4-benzoylisothiazoles have received little synthetic interest. Substituted isothiazoles and their carbocyclically fused derivatives have been the target of fundamental studies (for example: D.L. Pain, B.J. Peart, K.R.H. Wooldridge, Comprehensive Heterocyclic Chemistry,

Vol. 6, Part 4B, p. 131, ed. AR Katritzky, Pergamon Press, Oxford 1984), acylated and in particular benzoylated derivatives have been described only sporadically in the literature (for example: AJ Layton, E. Lunt, J. Chem. Soc. (1968) 611, A. Alberberola, F Alonso, P. Cuadrado, CM Sanudo, Synth. Commun. 17 (1987) 1207, A. Alberola, F. Alonso, P. Cuadrado, CM Sanudo, J. Heterocycl. Chem. 25 (1988) 235). Some 4-benzoyl-isothiazoles substituted by hydroxypropylaminocarbonyl have been investigated in EP 0 524 781 and EP 0 617 010 as muscle relaxants or as suitable therapeutic amides for incontinence. According to EP 0 449 223, 3,5-di- (tertiary-butyl) -4-hydroxybenzoyl-isothiazoles act as inhibitors of

5-lipoxygenase and cyclooxygenase anti-inflammatory.

The object of the invention was to provide new herbicidal active compounds with an improved active profile and crop tolerance.

Surprisingly, the benzoylisothiazoles of the general formula 1 according to the invention show pronounced herbicidal activity against harmful plants when tolerated by crop plants.

The present invention relates to 4-benzoylisothiazoles of the general formula 1

in which the substituents have the following meaning: X is oxygen or sulfur;

R ^{1 is} hydrogen, alkyl, alkenyl, alkynyl; if necessary subst. Alkoxycarbonyl;

if necessary subst. Aryl, if necessary subst. Heterocyclyl or possibly

subst. Hetaryl;

R ^{2 is} hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or

Cycloalkenyl, where these radicals can carry one or more of the following groups: halogen, alkyl, alkenyl or alkynyl;

Aryl, which radical can carry one or more of the following groups:

Alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio or alkenylthio, it being possible for these radicals to be partially or completely halogenated or to carry one or more of the following groups:

Alkoxy, alkenyloxy, aryloxy, alkylsulfonyl, alkenylsulfonyl or arylsulfonyl; Alkylsulfonyl or alkoxycarbonyl;

if necessary subst. Aryloxy or optionally subst. Arylthio; if necessary subst. Mono- or dialkylamino, optionally subst. Mono- or dialkylamino, optionally subst. Mono- or diaryl-amino or optionally subst. N-alkyl-N-arylamino, where alkyl and aryl can be the same or different;

Halogen, cyano or nitro;

Hetaryl or heterocyclyl, where these radicals can be partially or completely halogenated or can carry one or more of the following groups:

Alkyl, alkoxy or aryl and in the case of heterocyclyl at least one of the nitrogen can carry one of the following groups:

Alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, haloalkoxy, optionally subst, aryl or optionally subst. Aryloxy; R ^{3 is} a radical of the general formula 2a-d

in which n, A, B and the substituents R ⁴ , R ⁵ and R ^{6 have the} following meaning: n is zero, one or two A a chain (-CR ⁷ R ⁸ -), (-CR ⁷ R ⁸ -CR ⁹ R ¹⁰ -), (-CR ⁷ = CR ⁸ -),

(-CR ⁷ R ⁸ -CR ⁷ = CR ⁸ -) or a nitrogen atom, which in turn can be substituted by a substituent selected from the group hydrogen, alkyl, alkenyl, optionally substituted aryl or arylalkyl, alkoxy, halogen,

Haloalkyl or haloalkoxy;

B is a group consisting of C = O, C = NR ^11, CR ¹² -NR ¹³ R ¹⁴ ,

CR ¹² -OR ¹⁵ , CR ¹⁶ R ¹⁷ , CR ¹² -SR ¹⁵ , 1,3-dioxanyl or 1,3-dioxolanyl substituted with hydrogen or alkyl

Heteroatoms, selected from the group consisting of oxygen, sulfur or nitrogen, the nitrogen in turn being substituted by a substituent selected from the group consisting of hydrogen, alkyl, alkenyl, optionally substituted aryl or arylalkyl, alkoxy, halogen, haloalkyl or haloalkoxy, the bond between A and B can be saturated or unsaturated,

R ⁴ -R ⁶ can be identical or different and independently of one another represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl. Cycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, hydroxy, alkoxy, alkenyloxy, alkynyloxy,

Cycloalkoxy, cycloalkylalkoxy, cycloalkylalkenyloxy, cycloalkylalkynyloxy, cycloalkenyloxy, aryloxy, arylalkoxy, arylalkenyloxy, arylalkynyloxy, thio, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, cycloalkylalkylthio, cycloalkylalkenylthioylioio, cycloalkylthioylioio, thioylioio, thioyloalkylthioio Mono- or dialkylamino, optionally subst. Mono- or diarylamino, if necessary subst. N-alkylN-arylamino, where alkyl and aryl may be the same or different, alkenylamino, alkynylamino, cycloalkylamino, cycloalkenylamino, sulfonyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, cycloalkylsulfonyl, cycloalkylalkenylsulfylyl, , Sulfoxyl, alkyl sulfoxyl, alkenyl sulfoxyl, alkynyl sulfoxyl, cycloalkyl sulfoxyl, cycloalkylalkyl sulfoxyl, cycloalkylalkenyl sulfoxyl, cycloalkylalkynyl sulfoxyl, aryl sulfoxyl, arylalkyl sulfoxyl, arylalkenyl sulfoxyl, arylalkynyl sulfoxyl, aminosulfonyl, optionally subst. Mono- or dialkylaminosulfonyl, optionally subst. Mono- or diarylaminosulfonyl, optionally subst. N-alkyl-N-arylaminosulfonyl, where alkyl and Aryl may be the same or different, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, cycloalkylalkylcarbonyl, cycloalkylalkenylcarbonyl, cycloalkylalkynylcarbonyl, arylcarbonyl, arylalkylcarbonyl, arylalkenylcarbonyl, arylalkynylcarbonyl, carboxyl,

Alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkylalkenyloxycarbonyl, cycloalkylalkynyloxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl, arylalkenyloxycarbonyl, arylalkynyloxycarbonyl, aminocarbonyl, optionally subst. Mono or dialkylaminocarbonyl, optionally subst. Mono- or diarylaminocarbonyl, optionally subst. N-alkyl-N-arylaminocarbonyl, where alkyl and aryl can be the same or different, optionally subst. Mono- or dialkylcarbonylamino, optionally subst. Mono- or diarylaminocarbonyl, optionally subst. N-AlkylN-arylaminocarbonyl, where alkyl and aryl can be identical or different, alkoxyaminocarbonyl, Alkenyloxycarbonylamino, Alkinyloxycarbonylamino, Cycloalkoxycarbonylamino, Cycloalkylalkoxycarbonylamino, Cycloalkylalkenyloxycarbonylamino, Cycloalkylalkinyloxycarbonylamino, aryloxycarbonylamino, Arylalkoxycarbonylamino, Arylalkenyloxycarbonylamino, Arylalkinyloxycarbonylamino, halo, haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy, haloalkenyloxy, Haloalkynyloxy haloalkylthio, haloalkenylthio, haloalkynylthio, haloalkylamino, haloalkenylamino,

Haloalkinylamino, haloalkylsulfonyl, Haloalkenylsulfonyl, Haloalkinylsulfonyl, Haloalkylsulfoxyl, Haloalkenylsulfoxyl, Haloalkinylsulfoxyl, haloalkylcarbonyl, Haloalkenylcarbonyl, Haloalkinylcarbonyl, haloalkoxycarbonyl, Haloalkenyloxycarbonyl, Haloalkinyloxycarbonyl, Haloalkylamimocarbonyl, Haloalkenylaminocarbonyl, Haloalkinylaminocarbonyl, Haloalkoxycarbonylamino, Haloalkenyloxycarbonylamino, Haloalkinyloxycarbonylamino; Cyano or nitro; or one of the following groups:

R ⁷ , R ⁸ independently of one another are hydrogen, alkyl, haloalkyl,

Alkoxy, haloalkoxy; optionally substituted phenyl, where the substituents can consist of alkyl, alkoxy, haloalkoxy, haloalkyl, halogen, cyano, nitro;

R ^{9 is} hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy; optionally substituted phenyl, where the substituents can consist of alkyl, alkoxy, haloalkoxy, haloalkyl, halogen, cyano, nitro;

R ^{10 is} hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy; optionally substituted phenyl, where the substituents can consist of alkyl, alkoxy, haloalkoxy, haloalkyl, halogen, cyano, nitro;

R ^{11 is} hydrogen, -NR ⁹ R ⁴ ; Alkyl, haloalkyl, alkoxy, haloalkoxy, alkenyl, haloalkenyl, alkynyl; optionally substituted phenyl, where the substituents can consist of alkyl, alkoxy, haloalkoxy, haloalkyl, halogen, cyano, nitro; optionally substituted benzyl, where the substituents can consist of alkyl, alkoxy, haloalkoxy, haloalkyl, halogen, cyano, nitro;

optionally substituted benzyloxy where the substituents can consist of alkyl, alkoxy, haloalkoxy, haloalkyl, halogen, cyano, nitro;

R ^{12 is} hydrogen, alkyl, alkoxy, haloalkyl, haloalkoxy; optionally substituted phenyl, where the substituents can consist of one to three halogens, alkyl, alkoxy, haloalkoxy, nitro; R ¹² and R ⁷ or R ¹² and R ⁹ can form a bond;

R ¹³ , R ¹⁴ independently of one another are hydrogen, alkyl, alkenyl, haloalkyl, haloalkenyl, alkoxy, haloalkoxy;

optionally substituted phenyl, where the substituents can consist of alkyl, alkoxy, haloalkoxy, haloalkyl, halogen, cyano, nitro;

optionally substituted benzyl, where the substituents can consist of alkyl, alkoxy, haloalkoxy, haloalkyl, halogen, cyano, nitro;

R ^{15 is} hydrogen, alkyl, haloalkyl, optionally substituted phenyl, where the substituents can consist of alkyl, alkoxy, haloalkoxy, haloalkyl, halogen, cyano, nitro;

R ¹⁶ , R ¹⁷ independently of one another hydrogen, alkyl; optionally substituted phenyl, where the substituents can consist of one to three halogens, alkyl, alkoxy, haloalkoxy, nitro; R ¹⁶ and R ⁷ or R ¹⁶ and R ⁹ can form a formation; as well as customary salts of 4-benzoylisothiazoles of the general formula 1.

In the definitions of the compounds I given at the outset, collective terms were used which are generally representative of the following groups: Halogen: fluorine, chlorine, bromine and iodine;

Alkyl: straight-chain or branched alkyl groups with 1 to 6 or 10 carbon atoms, for example C ₁ -C ₆ -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl,

1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl,

3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl,

1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl,

1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl,

2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl- 2-methylpropyl; Alkylamino: an amino group which carries a straight-chain or branched alkyl group having 1 to 6 carbon atoms as mentioned above;

Dialkylamino: an amino group which carries two independent, straight-chain or branched alkyl groups each having 1 to 6 carbon atoms as mentioned above;

Alkylcarbonyl; straight-chain or branched alkyl groups with 1 to 10 carbon atoms, which are bonded to the skeleton via a carbonyl group (-CO-);

Alkylsulfonyl: straight-chain or branched alkyl groups with 1 to 6 or 10 carbon atoms, which have a sulfonyl group

(-SO ₂ -) are bound to the scaffold;

Alkvisulfoxyl: straight-chain or branched alkyl groups with 1 to 6 carbon atoms, which have a sulfoxyl group

(-S (= O) -) are bound to the framework; Alkylaminocarbonyl: alkylamino groups with 1 to 6 carbon atoms as mentioned above, which are bonded to the skeleton via a carbonyl group (-CO-);

Dialkylaminocarbonyl: dialkylamino groups each having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the skeleton via a carbonyl group (-CO-);

Alkylaminothiocarbonyl: alkylamino groups with 1 to 6 carbon atoms as mentioned above, which are bonded to the structure via a thiocarbonyl group (-CS-); Dialkylaminothiocarbonyl: dialkylamino groups each having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the skeleton via a thiocarbonyl group (-CS-); Haloalkyl; straight-chain or branched alkyl groups with 1 to 6 carbon atoms, in which groups the hydrogen atoms in these groups can be partially or completely replaced by halogen atoms as mentioned above, for example C ₁ -C ₂ -haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl , Dichlorf luormethyl,

Chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2- fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

Alkoxy: straight-chain or branched alkyl groups with 1 to 6 carbon atoms as mentioned above, which are bonded to the skeleton via an oxygen atom (-O-), for example C ₁ -C ₆ -alkoxy such as methyloxy, ethyloxy, propyloxy, 1-methylethyloxy, butyloxy , 1-methyl-propyloxy, 2-methylpropyloxy, 1,1-dimethylethyloxy, pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy,

2,2-dimethylpropyloxy, 1-ethylpropyloxy, hexyloxy, 1,1-dimethylpropyloxy, 1,2-dimethylpropyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyloxy, 1, 2-dimethylbutyloxy, 1,3-dimethylbutyloxy,

2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbutyloxy, 1,1,2-trimethylpropyloxy, 1,2,2-trimethylpropyloxy, 1-ethyl-1- methylpropyloxy and

1-ethyl-2-methylpropyloxy;

Alkoxycarbonyl: straight-chain or branched alkyl groups with 1 to 6 carbon atoms, which are bonded to the skeleton via an oxycarbonyl group (-OC (= O) -); Haloalkoxy: straight-chain or branched alkyl groups with 1 to 6 carbon atoms, in which groups the hydrogen atoms can be partially or completely replaced by halogen atoms as mentioned above, and where these groups are bonded to the structure via an oxygen atom;

Alkylthio: straight-chain or branched alkyl groups with 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the structure via a sulfur atom (-S-), e.g.

C ₁ -C ₆ alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2, 2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethyl propylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio,

1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and

1-ethyl-2-methylpropylthio;

Cycloalkyl: monocyclic alkyl groups with 3 to 6 carbon ring members, e.g. Cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

Al kenyl: straight-chain or branched alkenyl groups with 2 to 6 or 10 carbon atoms and a double bond in any position, for example C ₂ -C ₆ alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2 -Butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl ,

4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,

3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3- Methyl-3-butenyl, 1,1-dimethyl-2-propenyl,

1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl,

1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl,

2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4- Methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl- 4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,

1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl,

1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl,

1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,

2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl,

2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl,

3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,

1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,

2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,

1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,

1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

Alkenyloxy: straight-chain or branched alkenyl groups with 2 to 6 carbon atoms and a double bond in any position, which are bonded to the structure via an oxygen atom (-O-); Alkenylthio or alkenylamino: straight-chain or branched alkenyl groups with 2 to 6 carbon atoms and a double bond in any position which (alkenylthio) are bonded to the skeleton via a sulfur atom or (alkenylamino) a nitrogen atom.

Alkenyl carbonyl: straight-chain or branched alkenyl groups with

2 to 10 carbon atoms and a double bond in any position which are bonded to the skeleton via a carbonyl group (-CO-);

Alkynyl: straight-chain or branched alkynyl groups with 2 to 10 carbon atoms and a triple bond in any position, for example C ₂ -C ₆ -alkynyl such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentinyl,

3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2- Methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3- butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl; Alkynyloxy or alkynylthio and alkynylamino: straight-chain or branched alkynyl groups having 2 to 6 carbon atoms and a triple bond in any position which (alkynyloxy) via an oxygen atom or (alkynylthio) via a sulfur atom or (alkynylamino) via a nitrogen atom bonded to the skeleton are.

Alkynylcarbonyl: straight-chain or branched alkynyl groups with

3 to 10 carbon atoms and a triple bond in any position which are bonded to the skeleton via a carbonyl group (-CO-);

Cycloalkenyl or cycloalkenyloxy, cycloalkenylthlo and cycloalkenylamino: monocyclic alkenyl groups with 3 to 6 carbon ring members, which directly or (cycloalkenyloxy) via an oxygen atom or (cycloalkenylthio) a sulfur atom or

Cycloalkenylamino) are bound to the skeleton via a nitrogen atom, for example cyclopropenyl, cyclobutenyl, cyclopentenyl or cyclohexenyl. Cycloalkoxy or cycloalkylthio and cycloalkylamino: monocyclic alkyl groups with 3 to 6 carbon ring members which (cycloalkyloxy) via an oxygen atom or (cycloalkylthio) a sulfur atom or (cycloalkylamino) are bonded to the skeleton via a nitrogen atom, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; Cycloalkylcarbonyl: cycloalk groups, as defined above, which are bonded to the skeleton via a carbonyl group (-CO-);

Cycloalkoxycarbonyl: cycloalkoxy groups, as defined above, which are bonded to the skeleton via a carbonyl group (-CO-);

Alkenyloxycarbonyl: alkenyloxy groups, as defined above, which are bonded to the skeleton via a carbonyl group (-CO-);

Alkynyloxycarbonyl: alkynyloxy groups, as defined above, which are bonded to the skeleton via a carbonyl group (-CO-);

Heterocyclyl: three- to six-membered, saturated or partially unsaturated mono- or polycyclic heterocycles, which contain one to three heteroatoms selected from a group consisting of oxygen, nitrogen and sulfur, and which are bonded directly to the structure via carbon, e.g. 2-tetrahydrofuran, oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazole-dinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl 5-isothiazolidinyl, 3-pyrazolidinyl,

4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3- yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl,

1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2, 3-dihydrofur-3-yl,

2,3-dihydro-for-4-yl, 2,3-dihydro-for-5-yl, 2,5-dihydro-for-2-yl, 2,5-dihydro-fur-3-yl, 2, 3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,3-dihydrothien-4-yl, 2,3-dihydrothien-5-yl,

2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 2,3-dihydropyrrol-2-yl, 2,3-dihydropyrrol-3-yl, 2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisothiazol-3- yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydroisopyrazol-3-yl, 2,3-dihydroisopyrazol-4-yl, 2,3-dihy droisopyrazol-5-yl, 4,5-dihydroisopyrazol-3-yl, 4,5-dihydroisopyrazol-4-yl, 4,5-dihydroisopyrazol-5-yl, 2,5-dihydroisopyrazol-3-yl, 2,5-dihydroisopyrazol-4-yl, 2,5-dihydroisopyrazol-5-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5- yl, 4,5-dihydrooxazol-3-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-3-yl, 2,5-dihydrooxazol 4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 4,5-dihydro- thiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5- Dihydro-thiazol-5-yl, 2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4, 5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl,

2-morpholinyl, 3-morpholinyl, 2-piperidinyl, 3-piperidinyl,

4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydropyriminyl, 2-tetrahydropyrazinyl, 1,3,5-tetrahydrotriazin-2-yl, 1,2-yl 3-yl, 1,3-dihydrooxazin-2-yl,

1,3-dithian-2-yl, 2-tetrahydropyranyl, 1,3-dioxolan-2-yl,

3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl,

4H-3,1-benzothiazin-2-yl, 1,1-dioxo-2, 3,4,5-tetrahydrothien-2-yl, 2H-1,4-benzothiazin-3-yl, 2H-1,4- Benzoxazin-3-yl, 1,3-dihydro-oxazin-2-yl, 1,3-dithian-2-yl,

Aryl or aryloxy, arylthio, arylcarbonyl, aryloxycarbonyl, arylsulfonyl and arylsulfoxyl: aromatic mono- or polycyclic hydrocarbon radicals which are directly or (aryloxy) via an oxygen atom (-O-) or (arylthio) a sulfur atom (-S-), (Arylcarbonyl) via a carbonyl group (-CO-), aryloxycarbonyl via an oxycarbonyl group (-OCO-), (arylsulfonyl) via a sulfonyl group (-SO ₂ -) or arylsulfoxyl via a sulfoxyl group (-SO-), eg phenyl, naphthyl and phenanthrenyl or phenyloxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl and sulfonyl radicals;

Arylamino: aromatic mono- or polycyclic hydrocarbon residues, which are attached to the structure via a nitrogen atom.

Hetaryl: aromatic mono- or polycyclic radicals which, in addition to carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom and which are bonded directly to the structure via carbon, for example 5-membered heteroaryl containing one to three nitrogen atoms: 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three nitrogen atoms as ring members, for example 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl,

4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl,

1,2,4-triazol-3-yl and 1,3,4-triazol-2-yl; - 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or one sulfur atom: 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or a

Contain oxygen or sulfur atom as ring members

can, e.g. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl,

2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl,

5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl,

4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl,

5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl,

1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl,

1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl,

1,3,4-triazol-2-yl; - Carbocyclic annelated 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and / or one oxygen or sulfur atom: 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or

May contain oxygen atom or an oxygen or a sulfur atom as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member may be bridged by a buta-1,3-diene-1,4-diyl group; - 6-membered heteroaryl. containing one to three or one to four nitrogen atoms: 6-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three or one to four nitrogen atoms as ring members, e.g. 2-pyridinyl,

3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl,

2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl,

1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and

1,2,4,5-tetrazin-3-yl; - Benzo-fused 6-membered heteroaryl, containing one to four nitrogen atoms: 6-ring heteroaryl groups in which two adjacent carbon ring members can be bridged by a buta-1,3-diene-1,4-diyl group, for example

Quinoline, isoquinoline, quinazoline and quinoxaline, or the corresponding oxy, thio, carbonyl or sulfonyl groups. The expression "partially or fully halogenated" is intended to express that the hydrogen atoms in the groups characterized in this way can be replaced in part or in full by the same or different halogen atoms as mentioned above.

Possibly. subst. means that the corresponding organic group can be substituted as desired, in principle all substituents listed in this application are possible. Preferred substituents are hydrogen, alkyl, alkenyl,

Alkynyl, preferably cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, aryl, arylalkyl, arylalkenyl, hydroxy, alkoxy, alkenyloxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, arylalkoxy, thio, alkylthio, alkenylthio, cycloalkylthio, cycloalkylalkylthio, optionally arylthio, aryl. Mono- or dialkylamino, optionally subst. Mono- or diarylamino, if necessary subst. N-alkyl-N-arylamino, where alkyl and aryl can be the same or different, alkenylamino, cycloalkylamino, cycloalkenylamino,

Sulfonyl, alkylsulfonyl, alkenylsulfonyl, cycloalkylsulfonyl, cycloalkylalkylsulfonyl, arylsulfonyl, arylalkylsulfonyl,

Sulfoxyl, alkylsulfoxyl, Alkenylsulfoxyl, Cycloalkylsulfoxyl, Cycloalkylalkylsulfoxyl, arylsulfoxyl, Arylalkylsulfoxyl, alkylcarbonyl, AIkenylcarbonyl, cycloalkylcarbonyl, cycloalkylalkylcarbonyl, arylcarbonyl, arylalkylcarbonyl, carboxyl, alkoxycarbonyl, alkenyloxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, unsubstituted or substituted. Mono- or dialkylaminocarbonyl, if necessary

subst. Mono- or diarylaminocarbonyl, optionally subst. N-alkyl-N-arylaminocarbonyl, where alkyl and aryl may be the same or different, alkoxyaminocarbonyl, alkenyloxycarbonylamino, cycloalkoxycarbonylamino, aryloxycarbonylamino, arylalkoxycarbonylamino, halogen, haloalkyl, haloalkenyl, optionally subst. Mono- or dialkylamino, haloalkoxy, haloalkenyloxy, haloalkylthio, haloalkenylthio, haloalkylamino, haloalkenylamino, haloalkylsulfonyl, haloalkenylsulfonyl, haloalkylsulfoxyl, haloalkenylsulfoxyl,

Haloalkylcarbonyl, haloalkenylcarbonyl, haloalkoxycarbonyl, haloalkenyloxycarbonyl, haloalkylaminocarbonyl, haloalkenylamino carbonyl, haloalkoxycarbonylamino, haloalkenyloxycarbonylamino, hydroxy, cyano or nitro.

Particularly preferred substituents are hydrogen, alkyl,

Alkenyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, thio, alkylthio, cycloalkylthio, arylthio, amino, optionally subst. Mono- or dialkylamino, optionally subst. Mono- or diarylamino, if necessary subst. N-alkyl-N-arylamino, where alkyl and aryl can be the same or different, cycloalkylamino, sulfonyl, alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, sulfoxyl, alkylsulfoxyl, arylsulfoxyl, alkylcarbonyl, arylcarbonyl, carboxyl, alkoxycarbonyl, aryloxycarbonyl, aminocarbonyl, if necessary subst. Mono- or dialkylaminocarbonyl, if necessary

subst. Mono- or diarylaminocarbonyl, optionally subst. N-alkyl-N-arylaminocarbonyl, where alkyl and aryl can be identical or different, alkoxyaminocarbonyl, aryloxycarbonylamino, halogen, haloalkyl, haloalkoxy, haloalkylthio, Haloalkylamino, haloalkyl sulfonyl, Haloalkylsulfoxyl, haloalkylcarbonyl, haloalkoxy carbonyl, Haloalkoxycarbonylamino, hydroxy, cyano or Nitro.

In view of their biological activity, compounds of the general formula 1 in which X is oxygen are preferred.

Furthermore, compounds of the general formula 1 are preferred in which R ^{1 is} hydrogen or optionally subst. Alkoxycarbonyl means.

Preference is also given to compounds of the general formula 1 in which R ^{1 is} hydrogen or alkoxycarbonyl having 1 to 6 carbon atoms, which can be substituted one or more times by fluorine, chlorine or bromine.

Compounds of formula 1 in which R ^{1 is} hydrogen, methoxycarbonyl or ethoxycarbonyl are particularly preferred. Furthermore, compounds of the general formula 1 are preferred in which R ^{2 is} alkyl having 1 to 6 carbon atoms, particularly preferably methyl, ethyl, isopropyl or tertiary butyl; or cycloalkyl having 3 to 6 carbon atoms, particularly preferably cyclopropyl or 1-methylcyclopropyl; or aryl, which radical can carry one or more of the following groups:

Alkyl, alkoxy, alkylthio, where these radicals can be partially or completely halogenated or halogen, particularly preferably 3-trifluoromethylaryl, 2,4-difluoroaryl; Hetaryl or heterocyclyl, where these radicals can be partially or completely halogenated or can carry one or more of the following groups: alkyl, alkoxy or aryl, particularly preferably 1,3-benzodioxole, 2,2-difluoro-1,3-benzodioxole, 1,3-benzoxathiol, 3,3-dioxo-1,3-benzoxathiol, benzoxazole, pyrazolyl or thienyl.

In addition, compounds of the general formula 1 are preferred in which R ^{3 is} a radical of the general formula 2b or 2d,

mean, where n, A, B and the substituents R ⁴ , R ⁵ and R ^{6 have the} following meaning: n is zero, one or two, preferably one or two, particularly preferably two

A a chain (-CR ⁷ R ⁸ -), (-CR ⁷ R ⁸ -CR ⁹ R ¹⁰ -), (-CR ⁷ = CR ⁸ -),

(-CR ⁷ R ⁸ -CR ⁷ = CR ⁸ -) or a nitrogen atom, which in turn can be substituted by hydrogen, C ₁ -C ₆ alkyl, preferably methyl, ethyl, propyl, 1-methylethyl, butyl, 2-methylpropyl , Pentyl or hexyl; C ₂ -C ₆ alkenyl, preferably ethenyl, 2-propenyl, 2-butenyl or 3-butenyl; optionally substituted aryl, preferably phenyl or naphthyl or aryl-C ₁ -C ₆ alkyl; C ₁ -C ₆ alkoxy, preferably methyloxy, ethyloxy, propyloxy, 1-methylethyloxy, butyloxy, 2-methylpropyloxy, pentyloxy or hexyloxy; Halogen, preferably fluorine, chlorine, bromine or iodine; Haloalkyl, preferably chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2 -fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl; or haloalkoxy, preferably chloromethyloxy,

Dichloromethyloxy, trichloromethyloxy, fluoromethyloxy, difluoromethyloxy, trifluoromethyloxy, chlorofluoromethyloxy, dichlorofluoromethyloxy, chlorodifluoromethyloxy, 1-fluoroethyloxy, 2-fluoroethyloxy, 2,2-difluoroethyloxy, 2,2,2-trifluoroethyloxy, 2-chloro-2-fluoroethyloxy, 2-chloro-2,2-difluoroethyloxy, 2,2-dichloro-2-fluoroethyloxy, 2,2, -trichloroethyloxy. B is a group consisting of C = O, C = NR ¹¹ , CR ¹² -NR ¹³ R ¹⁴ ,

CR ¹² -OR ¹⁵ , CR ¹⁶ R ¹⁷ , CR ¹² -SR ¹⁵ , with hydrogen or

C ₁ -C ₆ alkyl-substituted 1,3-dioxanyl or 1,3-dioxolanyl, a heteroatom selected from the group consisting of oxygen, sulfur or nitrogen, where the nitrogen can in turn be substituted by hydrogen, C ₁ -C ₆ - Alkyl, preferably methyl, ethyl, propyl, 1-methylethyl, butyl, 2-methylpropyl, pentyl or hexyl, - C ₂ -C ₆ alkenyl, preferably ethenyl, 2-propenyl, 2-butenyl or 3-butenyl; optionally substituted aryl, preferably phenyl or naphthyl or aryl-C ₁ -C ₆ alkyl; C ₁ -C ₆ alkoxy, preferably methyloxy, ethyloxy, propyloxy, 1-methylethyloxy, butyloxy, 2-methylpropyloxy, pentyloxy or hexyloxy; Halogen, preferably fluorine, chlorine, bromine or iodine;

C ₁ -C ₆ haloalkyl, preferably chloromethyl, dichloromethyl, trichloromethyl, fluromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2nd -Chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl; or C ₁ -C ₆ haloalkoxy, preferably chloromethyloxy, dichloromethyloxy, trichloromethyloxy, fluoromethyloxy, difluoromethyloxy, trifluoromethyloxy, chlorofluoromethyloxy, dichlorofluoromethyloxy, chlorodifluoromethyloxy, 1-fluoroethyloxy, 2-fluoroethyloxy, 2,2-difluoroethyloxy, 2,2,2-oxyoxy, 2,2,2-trifluoromethyloxy 2-chloro-2-fluoroethyloxy, 2-chloro-2,2-difluoroethyloxy, 2,2-dichloro-2-fluoroethyloxy,

2,2,2-trichloroethyloxy;

R ⁴ -R ⁶ can be the same or different and independently of one another represent hydrogen, C ₁ -C ₆ alkyl, preferably methyl, ethyl, propyl, 1-methylethyl, butyl, 2-methylpropyl, pentyl or hexyl; C ₂ -C ₆ alkenyl, preferably ethenyl, 2-propenyl, 2-butenyl or 3-butenyl; C ₂ -C ₆ alkynyl, ethynyl, 2-propynyl, 2-butynyl or 3-butynyl; C ₃ -C ₆ cycloalkyl, preferably cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl-C ₂ -C ₆ alkenyl,

C ₃ -C ₆ cycloalkyl-C ₂ -C ₆ -alkynyl, aryl, preferably phenyl or naphthyl, aryl-C ₁ -C ₆ -alkyl, aryl-C ₂ -C ₆ -alkenyl, aryl-C ₂ -C ₆ -alkynyl; Hydroxy, C ₁ -C ₆ alkoxy, preferably methyloxy, ethyloxy, propyloxy, 1-methylethyloxy,

Butyloxy, pentyloxy or hexyloxy, C ₂ -C ₆ alkenyloxy, preferably ethenyloxy, 2-propenyloxy, 2-butenyloxy or 3-butenyloxy; C ₂ -C ₆ alkynyloxy, preferably ethynyloxy, 2-propynyloxy, 2-butynyloxy or 3-butynyloxy;

C ₃ -C ₆ cycloalkoxy, preferably cyclopropyloxy, cyclobutyloxy, cyclopentyloxy or cyclohexyloxy, C ₃ -C ₆ cycloalkyl-C ₁ -C ₆ alkoxy, C ₃ -C ₆ cycloalkyl-C ₂ -C ₆ alkynyloxy;

Aryloxy, preferably phenoxy or naphthyloxy,

Aryl-C ₁ -C ₆ -alkoxy, aryl-C ₂ -C ₆ -alkenyloxy,

Aryl-C ₂ -C ₆ alkynyloxy; Thio; C ₁ -C ₆ alkylthio, preferably methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, pentylthio or hexylthio; C ₂ -C ₆ alkenylthio, preferably ethenylthio, 2-propenylthio, 2-butenylthio or 3-butenylthio; C ₂ -C ₆ alkynylthio, preferably ethynylthio, 2-propynyltio, 2-butynylthio or

3-butynylthio; C ₃ -C ₆ cycloalkylthio, preferably cyclopropylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio, C ₃ -C ₆ cycloalkyl-C ₁ -C ₆ alkylthio, C ₃ -C ₆ cycloalkyl-C ₂ -C ₆ alkenylthio, C ₃ -C ₆ cycloalkyl-C ₂ -C ₆ alkynylthio; Arylthio, preferably phenylthio or naphthylthio, aryl-C ₁ -C ₆ -alkylthio,

Aryl-C ₂ -C ₆ -alkenylthio, aryl-C ₂ -C ₆ -alkynylthio; Amino, if necessary subst. Mono- or di-C ₁ -C ₆ alkylamino, optionally subst. Mono- or diarylamino, if necessary subst. NC ₁ -C ₆ alkyl-narylamino, where alkyl and aryl may be the same or different; Sulfonyl; C ₁ -C ₆ alkylsulfonyl, preferably methylsulfonyl, ethylsulfonyl, propylsulfonyl,

1-methylethylsulfonyl, butylsulfonyl, 2-methylpropylsulfonyl, pentylsulfonyl or hexylsulfonyl;

C ₃ -C ₆ cycloalkylsulfonyl, preferably cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₆ alkylsulfonyl, C ₃ -C ₆ cycloalkyl-C ₂ -C ₆ alkenylsulfonyl,

C ₃ -C ₆ cycloalkyl-C ₂ -C ₆ alkynylsulfonyl; Arylsulfonyl, preferably phenylsulfonyl or naphthylsulfonyl,

Aryl-C ₁ -C ₆ -alkylsulfonyl, aryl-C ₂ -C ₆ -alkenylsulfonyl, aryl-C ₂ -C ₆ -alkynylsulfonyl; Aminosulfonyl, optionally subst.

Mono- or dialkylaminosulfonyl, optionally subst. Mono- or diarylaminosulfonyl, optionally subst. N-alkyl-N-arylaminosulfonyl, where alkyl and aryl can be the same or different, sulfoxyl; C ₁ -C ₆ alkyl sulfoxyl, preferably methyl sulfoxyl, ethyl sulfoxyl, propyl sulfoxyl, 1-methyl ethyl sulfoxyl, butyl sulfoxyl, 2-methyl propyl sulfoxyl, pentyl sulfoxyl or hexyl sulfoxyl; C ₃ -C ₆ cycloalkylsulfoxyl, preferably cyclopropylsulfoxyl, cyclobutylsulfoxyl, cyclopentylsulfoxyl or cyclohexylsulfoxyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₆ alkylsulfoxyl, C ₃ -C ₆ cycloalkyl-C ₂ -C ₆ -alkenylsulfoxyl, C ₃ -C ₆ cycloalkyl-C ₂ -C ₆ alkynyl sulfoxyl; Arylsulfoxyl, preferably phenylsulfoxyl or naphthylsulfoxyl, aryl-C ₁ -C ₆ -alkylsulfoxyl,

Aryl-C ₂ -C ₆ -alkenylsulfoxyl, aryl-C ₂ -C ₆ -alkynylsulfoxyl; C ₁ -C ₆ alkylcarbonyl, preferably methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 2-methylpropylcarbonyl, pentylcarbonyl or

Hexylcarbonyl; C ₂ -C ₆ alkenylcarbonyl, preferably ethenylcarbonyl, 2-propenylcarbonyl, 2-butenylcarbonyl or 3-butenylcarbonyl; C ₂ -C ₆ alkynylcarbonyl, preferably ethynylcarbonyl, 2-propynylcarbonyl, 2-butynylcarbonyl or 3-butynylcarbonyl; C ₃ -C ₆ cycloalkylcarbonyl, preferably cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl or cyclohexylcarbonyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₆ alkylcarbonyl, C ₃ -C ₆ cycloalkyl-C ₂ -C ₆ alkenylcarbonyl, C ₃ -C ₆ cycloalkyl-C ₂ -C ₆ alkynylcarbonyl; Arylcarbonyl, preferred

Phenylcarbonyl or naphthylcarbonyl, aryl-C ₁ -C ₆ -alkylcarbonyl, aryl-C ₂ -C ₆ -alkenylcarbonyl,

Aryl-C ₂ -C ₆ alkynylcarbonyl; Carboxyl; C ₁ -C ₆ alkoxycarbonyl, methyloxycarbonyl, ethyloxycarbonyl, propyloxycarbonyl, 1-methylethyloxycarbonyl, butyloxycarbonyl, pentyloxycarbonyl or hexyloxycarbonyl, C ₂ -C ₆ alkenyloxycarbonyl, C ₂ -C ₆ alkynyloxycarbonyl, C ₃ -C ₆ cycloalkoxycarbonyl, cyclopropyloxycarbonyl Cyclobutyloxycarbonyl, cyclopentyloxycarbonyl or cyclohexyloxycarbonyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₆ alkoxycarbonyl, C ₃ -C ₆ cycloalkyl-C ₂ -C ₆ alkenyloxycarbonyl, C ₃ -C ₆ cycloalkyl-C ₂ -C _6- alkynyloxycarbonyl; Aryloxycarbonyl, preferably phenyloxycarbonyl or naphthyloxycarbonyl, aryl-C ₁ -C ₆ -alkoxycarbonyl, aryl-C ₂ -C ₆ -alkenyloxycarbonyl, aryl-C ₂ -C ₆ -alkynyloxycarbonyl; Aminocarbonyl; if necessary subst. Mono- or di-C ₁ -C ₆ alkylaminocarbonyl, optionally subst. Mono- or diarylaminocarbonyl, optionally subst. NC ₁ -C ₆ alkyl-N-arylaminocarbonyl, where alkyl and aryl can be the same or different, optionally subst. Mono- or di-C ₁ -C ₆ alkylcarbonylamino, optionally subst. Mono- or diarylcarbonylamino, optionally subst. NC ₁ -C ₆ alkyl-N-arylcarbonylamino, where alkyl and aryl may be the same or different, C ₁ -C ₆ alkoxyaminocarbonyl, preferably methyloxyaminocarbonyl, ethyloxyaminocarbonyl, propyloxyaminocarbonyl, 1-methylethyloxyaminocarbonyl, butyloxyaminocarbonyl, 2-methylpropyloxyylylaminocarbonylamine, pentane ; C ₂ -C ₆ alkenyloxycarbonylamino, preferably ethyleneoxyaminocarbonyl, 2-propenyloxyaminocarbonyl, 2-butenyloxyaminocarbonyl or 3-butenyloxyaminocarbonyl; C ₂ -C ₆ alkynyloxycarbonylamino, preferably ethynyloxyaminocarbonyl, 2-propynyloxyaminocarbo nyl, 2-butynyloxyaminocarbonyl or 3-butynyloxyaminocarbonyl; C ₃ -C ₆ cycloalkoxy-aminocarbonyl, preferably cyclopropyloxyaminocarbonyl, cyclobutyloxyaminocarbonyl, cyclopentyloxyaminocarbonyl or cyclohexyloxyaminocarbonyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₆ alkoxyaminocarbonyl,

C ₃ -C ₆ cycloalkyl-C ₂ -C ₆ alkenyloxyaminocarbonyl,

C ₃ -C ₆ cycloalkyl-C ₁ -C ₆ alkynyloxyaminocarbonyl; Aryloxyaminocarbonyl, preferably phenyloxyaminocarbonyl or naphthyloxyaminocarbonyl, aryl-C ₁ -C ₆ -alkoxyaminocarbonylamino, aryl-C ₂ -C ₆ -alkenyloxyaminocarbonyl,

Aryl-C ₂ -C ₆ alkynyloxyaminocarbonyl; Halogen, preferably fluorine, chlorine, bromine or iodine; C ₁ -C ₆ haloalkyl, preferably chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,

1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,

2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,

2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkynyl; C ₁ -C ₆ haloalkoxy, preferred

Chloromethyl, dichloromethyl, trichloromethyl, fluoromethyloxy, difluoromethyloxy, trifluoromethyloxy, chlorofluoromethyloxy, dichlorofluoromethyloxy, chlorodifluoromethyloxy, 1-fluoroethyloxy, 2-fluoroethyloxy,

2,2-difluoroethyloxy, 2,2,2-trifluoroethyloxy,

2-chloro-2-fluoroethyloxy, 2-chloro-2,2-difluoroethyloxy, 2,2-dichloro-2-fluoroethyloxy, 2,2,2-trichloroethyloxy or pentafluoroethyloxy, C ₂ -C ₆ haloalkenyloxy,

C ₂ -C ₆ haloalkynyloxy; C ₁ -C ₆ haloalkylthio, preferably chloromethylthio, dichloromethylthio, trichloromethylthio,

Fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio,

2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,

2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio or pentafluoroethylthio, C ₂ -C ₆ haloalkenylthio,

C ₂ -C ₆ haloalkynylthio; C ₁ -C ₆ haloalkylamino, preferably chloromethylamino, dichloromethylamino, trichloromethylamino, fluoromethylamino, difluoromethylamino, trifluoromethylamino, chlorofluoromethylamino, dichlorofluoromethylamino, chlorodifluoromethylamino, 1-fluoroethylamino, 2-fluoroethylamino, 2,2

2,2,2-trifluoroethylamino, 2-chloro-2-fluoroethylamino, 2-chloro-2,2-difluoroethylamino, 2,2-dichloro-2-fluoroethylamino, 2,2,2-trichloroethylamino or pentafluoroethylamino, C ₂ -C ₆ -Halo-alkenylamino, C ₂ -C ₆ -Haloalkiny- lamino, C ₁ -C ₆ haloalkylsulfonyl, preferably chloromethylsulfonyl, dichloromethylsulfonyl, trichloromethylsulfonyl, fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl, chlorodifonyl

1-fluoroethylsulfonyl, 2-fluoroethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl,

2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl,

2,2,2-trichloroethylsulfonyl or pentafluoroethylsulfonyl, C ₂ -C ₆ haloalkenylsulfonyl, C ₂ -C ₆ haloalkynylsulfonyl; C ₁ -C ₆ haloalkylcarbonyl, preferably chloromethylcarbonyl, dichloromethylcarbonyl, trichloromethylcarbonyl, fluoromethylcarbonyl, difluoromethylcarbonyl, trifluoromethylcarbonyl, chlorofluoromethylcarbonyl, dichlorofluoromethylcarbonyl, chlorodifluoromethylcarbonyl,

1-fluoroethylcarbonyl, 2-fluoroethylcarbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl,

2-chloro-2-fluoro-ethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoro-ethylcarbonyl,

2-2-2-trichloroethylcarbonyl or pentafluoroethylcarbonyl, C ₂ -C ₆ haloalkenylcarbonyl, C ₂ -C ₆ haloalkynylcarbonyl; C ₁ -C ₆ haloalkoxycarbonyl, preferably chloromethyloxycarbonyl, dichloromethyloxycarbonyl, trichloromethyloxycarbonyl, fluoromethyloxycarbonyl, difluoromethyloxycarbonyl, trifluoromethyloxycarbonyl, chlorofluoromethyloxycarbonyl, dichlorofluoromethyloxycarbonyl, chlorodifluoromethyloxycarbonyl, 1-fluoroethyloxycarbonyl

2-fluoroethyloxycarbonyl, 2,2-difluoroethyloxycarbonyl, 2,2,2-trifluoroethyloxycarbonyl, 2-chloro-2-fluoroethyloxycarbonyl, 2-chloro-2,2-difluoroethyloxycarbonyl, 2,2-dichloro-2-fluoroethyloxycarbonyl, 2,2,2-trichloroethyloxycarbonyl or pentafluoroethyloxycarbonyl, C ₂ -C ₆ haloalkenyloxycarbonyl, C ₂ -C ₆ haloalkynyloxycarbonyl; C ₁ -C ₆ haloalkylaminocarbonyl, preferably chloromethylaminocarbonyl, dichloromethylaminocarbonyl, trichloromethylaminocarbonyl, fluoromethylaminocarbonyl, difluoromethylaminocarbonyl, trifluoromethylaminocarbonyl, chlorofluoromethylaminocarbonyl, dichlorofluoromethylcarbonyl, fluorocarbonyl, 2,2-fluorocarbonyl, fluoro-2-fluoro-2-fluoro-2-fluoro-2-fluoro-2-fluoro-2-fluoro-2-fluoro-2-fluoro-2-fluoro-2-fluoro-2-fluoro-2-fluoro-2-fluoro-2-fluoro-2, , 2-chloro-2-fluoroethylamino-carbonyl,

2-chloro-2,2-difluoroethylaminocarbonyl, 2,2-dichloro-2-fluoroethylaminocarbonyl, 2, 2,2-trichloroethylaminocarbonyl or pentafluoroethylaminocarbonyl,

C ₂ -C ₆ haloalkenylaminocarbonyl, C ₂ -C ₆ haloalkynylami nocarbonyl; C ₁ -C ₆ haloalkoxycarbonylamino, chloromethyloxyaminocarbonyl, dichloromethyloxycarbonyl, trichloromethyloxyaminocarbonyl, fluoromethyloxyaminocarbonyl, difluoromethyloxyaminocarbonyl, trifluoromethyloxyaminocarbonyl, chlorofluoromethyloxyaminocarbonyl,

Dichlorofluoromethyloxyaminocarbonyl, chlorodifluoromethyloxyaminocarbonyl, 1-fluoroethyloxyaminocarbonyl, 2-fluoroethyloxyaminocarbonyl, 2,2-difluoroethyloxyaminocarbonyl, 2,2,2-trifluoroethyloxyaminocarbonyl,

2-chloro-2-fluoroethyloxyaminocarbonyl, 2-chloro-2,2-difluoroethyloxyaminocarbonyl, 2,2-dichloro-2-fluoroethyloxy-aminocarbonyl, 2,2,2-trichloroethyloxyaminocarbonyl or pentafluoroethyloxyaminocarbonyl, C ₂ -C ₆ haloalkenyloxycarbonylamino, C ₂ -C ₆ haloalkynyloxycarbonylamino, cyano or nitro;

R ⁷ , R ⁸ independently of one another are hydrogen, C ₁ -C ₆ -alkyl, preferably methyl, ethyl, propyl, 1-methylethyl, butyl, 2-methylpropyl, pentyl or hexyl; C ₁ -C ₆ haloalkyl, preferably chloromethyl, dichloromethyl, trichloromethyl,

Fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2, difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl; C ₁ -C ₆ alkoxy, preferably methyloxy, ethyloxy, propyloxy, 1-methylethyloxy, butyloxy, pentyloxy or hexyloxy: C ₁ -C ₆ haloalkoxy, preferably chloromethyl, dichloromethyl, trichloromethyl, fluoromethyloxy, difluoromethyloxy, trifluoromethyloxy, chlorofluoromethyloxy,

Dichlorofluoromethyloxy, chlorodifluoromethyloxy, 1-fluoroethyloxy, 2-fluoroethyloxy, 2,2-difluoroethyloxy, 2,2,2-trifluoroethyloxy, 2-chloro-2-fluoroethyloxy, 2-chloro-2,2-difluoroethyloxy, 2,2-dichloro- 2-fluoroethyloxy, 2,2,2-trichloroethyloxy or pentafluoroethyloxy; optionally substituted aryl, preferably phenyl or

Naphthyl, where the substituents can consist of C ₁ -C ₄ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkyl, halogen, cyano, nitro;

R ^{9 is} hydrogen, C ₁ -C ₆ alkyl, preferably methyl, ethyl,

Propyl, 1-methylethyl, butyl, 2-methylpropyl, pentyl or hexyl; C ₁ -C ₆ haloalkyl, preferably chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2nd -Chloro-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl;

C ₁ -C ₆ alkoxy, preferably methyloxy, ethyloxy, propyloxy, 1-methylethyloxy, butyloxy, pentyloxy or hexyloxy; C ₁ -C ₆ haloalkoxy, preferably chloromethyl, dichloromethyl,

Trichloromethyl, fluoromethyloxy, difluoromethyloxy, trifluoromethyloxy, chlorofluoromethyloxy, dichlorofluoromethyloxy, chlorodifluoromethyloxy, 1-fluoroethyloxy, 2-fluoroethyloxy, 2,2-difluoroethyloxy, 2,2,2-trifluoroethyloxy, 2-chloro-fluoroethyloxy, 2-chloro-2,2- difluoroethyloxy,

2,2-dichloro-2-fluoroethyloxy, 2,2,2-trichloroethyloxy or pentafluoroethyloxy; optionally substituted aryl, preferably phenyl or naphthyl, where the substituents can consist of C ₁ -C ₄ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₄ alkoxy, C ₁ - C ₄ haloalkoxy, C ₁ -C ₄ haloalkyl, halogen, cyano, nitro;

R ^{10 is} hydrogen,

C ₁ -C ₆ alkyl, preferably methyl, ethyl, propyl, 1-methylethyl, butyl, 2-methylpropyl, pentyl or hexyl; C ₁ -C ₆ haloalkyl, preferably chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2, 2-difluoroethyl, 2,2,2-trifluoroethyl, 2nd -Chlor-2-fluoroethyl,

2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl;

C ₁ -C ₆ alkoxy, preferably methyloxy, ethyloxy, propyloxy, 1-methylethyloxy, butyloxy, pentyloxy or hexyloxy:

C ₁ -C ₆ haloalkoxy, preferably chloromethyl, dichloromethyl, trichloromethyl, fluoromethyloxy, difluoromethyloxy, trifluoromethyloxy, chlorofluoromethyloxy, dichlorofluoromethyloxy, chlorodifluoromethyloxy, 1-fluoroethyloxy, 2-fluoroethyloxy, 2,2-difluoroethyloxy, 2,2,2-2-trifluoroethyl -Chloro-2-fluoroethyloxy, 2-chloro-2,2-difluoroethyloxy,

2,2-dichloro-2-fluoroethyloxy, 2,2,2-trichloroethyloxy or pentafluoroethyloxy; optionally substituted aryl, preferably phenyl or naphthyl, where the substituents can consist of C ₃ -C ₄ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₄ alkoxy, C ₁ - C ₄ haloalkoxy, C ₁ -C ₄ haloalkyl, halogen, cyano, nitro;

R ¹¹ hydrogen, optionally subst. Mono- or di-C ₁ -C ₆ alkylamino, optionally subst. Mono- or diarylamino or optionally subst.

NC ₁ -C ₆ alkyl-N-arylamino, where alkyl and aryl may be the same or different; C ₁ -C ₆ alkyl, preferably methyl, ethyl, propyl, 1-methylethyl, butyl, 2-methylpropyl, pentyl or hexyl; C ₁ -C ₆ haloalkyl, preferably chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2, 2-trifluoroethyl, 2nd -Chloro-2-fluoroethyl, 2-chloro-2,2, -difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl;

C ₁ -C ₆ haloalkoxy, preferably chloromethyl, dichloromethyl, trichloromethyl, fluoromethyloxy, difluoromethyloxy, trifluoromethyloxy, chlorofluoromethyloxy, dichlorofluoromethyloxy, chlorodifluoromethyloxy, 1-fluoroethyloxy, 2-fluoroethyloxy, 2,2-difluoroethyloxy, 2,2,2-2-trifluoroethyl -Chlor-2-fluoroethyloxy, 2-chloro-2,2-difluoroethyloxy, 2,2-dichloro-2-fluoroethyloxy, 2,2,2-trichloroethyloxy or pentafluoroethyloxy;

C ₂ -C ₆ alkenyl, preferably ethenyl, 2-propenyl, 2-butenyl or 3-butenyl; C ₂ -C ₆ alkynyl, ethynyl, 2-propynyl, 2-butynyl or 3-butynyl; C ₂ -C ₆ haloalkenyl;

optionally substituted aryl, preferably phenyl or naphthyl, where the substituents can consist of C ₁ -C ₄ alkyl, C ₂ -C ₆ alkynyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ - C ₄ haloalkyl, halogen, cyano, nitro; optionally substituted benzyl, where the substituents can consist of C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkyl, halogen, cyano, nitro;

optionally substituted benzyloxy, where the substituents can consist of C ₁ -C ₄ alkyl,

C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkyl, halogen, cyano, nitro; R ^{12 is} hydrogen, C ₁ -C ₆ alkyl, preferably methyl, ethyl,

Propyl, 1-methylethyl, butyl, 2-methylpropyl, pentyl or hexyl; C ₁ -C ₆ haloalkyl, preferably chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2nd -Chlorofluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl;

C ₁ -C ₆ alkoxy, preferably methyloxy, ethyloxy, propyloxy, 1-methylethyloxy, butyloxy, pentyloxy or hexyloxy;

C ₁ -C ₆ haloalkoxy, preferably chloromethyl, dichloromethyl, trichloromethyl, fluoromethyloxy, difluoromethyloxy, tri fluoromethyloxy, chlorofluoromethyloxy, dichlorofluoromethyloxy, chlorodifluoromethyloxy, 1-fluoroethyloxy, 2-fluoroethyloxy, 2,2-difluoroethyloxy, 2,2,2-trifluoroethyloxy, 2-chlorofluoroethyloxy, 2-chloro-2,2-difluoroethyloxy, 2,2- Dichloro-2-fluoroethyloxy, 2,2,2-trichloroethyloxy or

Pentafluoroethyloxy; optionally substituted aryl, preferably phenyl or naphthyl, where the substituents can consist of C ₁ -C ₄ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkyl, halogen, cyano, nitro;

R ¹³ -R ¹⁴ independently of one another are hydrogen, C ₁ -C ₆ alkyl, preferably methyl, ethyl, propyl, 1-methylethyl, butyl, 2-methylpropyl, pentyl or hexyl; C ₂ -C ₆ alkenyl, preferably ethenyl, 2-propenyl, 2-butenyl or 3-butenyl, C ₁ -C ₆ haloalkyl, preferably chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,

2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl; C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ alkoxy, preferably methyloxy, ethyloxy, propyloxy, 1-methylethyloxy, butyloxy, pentyloxy or hexyloxy; C ₁ -C ₆ haloalkoxy, preferably chloromethyl, dichloromethyl, trichloromethyl, fluoromethyloxy, difluoromethyloxy, trifluoromethyloxy, chlorofluoromethyloxy, dichlorofluoromethyloxy, chlorodifluoromethyloxy, 1-fluoroethyloxy, 2-fluoroethyloxy, 2,2-difluoroethyloxy, 2,2,2-2-trifluoroethyl -Chloro-2-fluoroethyloxy, 2-chloro-2,2-difluoroethyloxy,

2,2-dichloro-2-fluoroethyloxy, 2,2,2-trichloroethyloxy or pentafluoroethyloxy; optionally substituted aryl, preferably phenyl or naphthyl, where the substituents can consist of C ₁ -C ₄ alkyl, C ₂ -C ₆ alkenyl,

C ₂ -C ₆ alkynyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkyl, halogen, cyano, nitro;

and optionally substituted benzyl, where the substituents can consist of C ₁ -C ₄ alkyl,

C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkyl, halogen, cyano, nitro;

R ^{15 is} hydrogen,

C ₁ -C ₆ alkyl, preferably methyl, ethyl, propyl, 1-methylethyl, butyl, 2-methylpropyl, pentyl or hexyl; C ₁ -C ₆ haloalkyl, preferably chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorine difluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2, -difluoroethyl, 2,2-dichloro-2 -fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl;

optionally subst. Aryl, preferably phenyl or

Naphthyl, where the substituents can consist of C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkyl, halogen, cyano, nitro; optionally substituted benzyl, where the substituents can consist of C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkyl, halogen, cyano, nitro;

R ¹⁶ , R ¹⁷ independently of one another are hydrogen, C ₁ -C ₆ alkyl; preferably methyl, ethyl, propyl, 1-methylethyl, butyl, 2-methylpropyl, pentyl or hexyl;

optionally substituted aryl, preferably phenyl or naphthyl, where the substituents can consist of one to three halogens, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, nitro.

In addition, particular preference is given to compounds of the general formula 1 in which R ^{3 is} a radical of the general formula 2b or 2d,

means in which n, A and B has the meaning given above and R ⁴ -R ^{6 have} the following meaning:

R ⁴ -R ⁶ may be the same or different and are independently hydrogen, alkyl, cycloalkyl, aryl,

Hydroxy, alkoxy, cycloalkoxy, aryloxy, thio, alkylthio, cycloalkylthio, arylthio, amino, optionally substituted mono- or dialkylamino or mono- or diarylamino or N-alkyl-N-arylamino, where alkyl and aryl can be the same or different , Cycloalkylamino, sulfonyl,

Alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, sulfoxyl, alkylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, Alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl,

Carboxyl, alkoxycarbonyl, cycloalkoxycarbonyl, aryloxycarbonyl, aminocarbonyl, optionally substituted mono- or dialkylaminocarbonyl or mono- or diarylaminocarbonyl or N-alkyl-N-arylaminocarbonyl, where alkyl and aryl may be the same or different, alkoxyaminocarbonyl, cycloalkoxycarbonylamino, aryloxycarbonylam , Haloalkyl, Haloalkoxy, Haloalkylthio, Haloalkylamino, Haloalkylsulfonyl, Haloalkylsulfoxyl, Haloalkylcarbonyl, Haloalkoxycarbonyl, Haloalkylamimocarbonyl, Haloalkoxycarbonylamino, Cyano or Nitro.

Compounds of the general formula 1 in which R ^{3 is} a radical of the general formula 2b or 2d are also preferred

R ⁴ -R ⁶ can be the same or different and independently of one another represent hydrogen, alkyl, hydroxy, alkoxy,

Sulfonyl, sulfonylalkyl, halogen, haloalkyl, cyano or nitro.

Also preferred are compounds of the general formula 1 in which R ^{3 is} a radical of the formula 2e,

R represents in which R ⁵ and R ^{6 represent} hydrogen, C ₁ -C ₆ alkyl,

C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl,

C ₁ -C ₄ haloalkoxy, halogen, nitro or cyano and R ⁴ for hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₄ alkoxy , C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, halogen, nitro or cyano and n, B, R ⁷ , R ⁸ , R ⁹ and R ^{10 have} the meanings given in Claim 1. Also preferred are compounds of the general formula 1 in which R ^{3 is} a radical of the formula 2f

in which R ⁵ and R ^{6 are} hydrogen, C ₁ -C ₆ alkyl,

C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, halogen, nitro or cyano and R ⁴ for hydrogen , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, halogen , Nitro or cyano and n, B, R ⁷ and R ^{8 have} the meanings given in claim 1.

Also preferred are compounds of the general formula 1 in which R ³ for a radical of the formula 2g g in which R ⁴ and R ^{5 are} hydrogen, C ₁ -C ₆ alkyl,

C ₁ -C ₄ haloalkoxy, halogen nitro or cyano and R ⁴ for hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, halogen nitro or cyano and n, B, R ⁷ and R ^{8 have} the meanings given in claim 1.

Also preferred are compounds of the general formula 1 in which R ^{3 is} a radical of the formula 2a-d

is in which n is one or two and B is CR ¹² -OR ¹⁵ , wherein R ¹² and R ^{15 have} the meaning given in claim 1.

Also preferred are compounds of the general formula 1 in which R ^{3 represents} a radical of the formulas 2b or 2d

R

R stands in which n, B, R ⁴ , R ⁵ and R ^{6 have} the meaning given in claim 1 and A represents a nitrogen atom, which in turn can be substituted by hydrogen, C ₂ -C ₆ alkyl,

C ₂ -C ₆ alkenyl, optionally substituted aryl or aryl-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, halogen, C ₁ -C ₆ haloalkyl or C ₂ -C ₆ haloalkoxy.

Also preferred are compounds of the general formula 1 in which R ^{3 is} a radical of the formula of the formulas 2b or 2d is in which n, R ⁴ , R ⁵ and R ^{6 have} the meaning given in claim 1 and A represents a nitrogen atom, which in turn can be substituted by hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl , optionally substituted aryl or aryl-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, halogen, C ₁ -C ₆ haloalkyl or C ₁ -C ₆ haloalkoxy and BC = O means.

Also preferred are compounds of the general formula 1 in which the substituents are selected from a combination of the preferred substituents listed above.

4-Benzoylisothiazoles of the general formula 1 are a) by reaction of the isothiazole halogen compounds 3

in which R ¹ and R ^{2 have} the meaning described above and Y is preferably chlorine, bromine or iodine with elemental magnesium, an organomagnesium or an organolithium compound and a carboxylic acid derivative of the general formula 4

4 in which R ^{3 has} the meaning described above and R ^{18 is} halogen, preferably chlorine, bromine or iodine or N-alkoxy-N-alkylamino, preferably N-methoxy-N-methyl or cyano in the presence an inert solvent in a temperature range from -78 ° C to 111 ° C, preferably in a temperature range from -20 ° C to 111 ° C (A. Alberola, F. Alonso, P. Cuadrado, MC Sanudo, Synth. Commun. 17 (1987) 1207), or b. by reacting a halogenobenzene of the general formula 5 in which R ^{3 has} the meaning described above and Y is halogen, preferably chlorine, bromine or iodine with elemental

Magnesium, an organomagnesium or an organolithium compound and an isothiazolecarboxylic acid derivative of the general formula 6a or 6b,

in which X, R ¹ and R ^{2 have} the meaning described above and R ^{18 is} halogen, preferably chlorine, bromine or iodine and N-alkoxy-N-alkylamino, preferably N-methoxy-N-methyl in the presence of an inert solvent5 accessible in a temperature range from -78 ° C to 111 ° C, preferably in a temperature range from -20 ° C to 111 ° C (A. Alberola, F. Alonso, P Cuadrado, MC Sanudo, J. Heterocyclic Chem. 25 (1988 ) 235).

The synthesis of the isothiazole halogen compounds 3 is carried out by halogenation using methods known from the literature (representative: A. Alberola, F. Alonso, P. Cuadrado, M. C. Sanudo, Synth.

Commun. 17 (1987) 1207; b. Vasilevskii, Izv. Akad. Nauk. SSSR Ser. Khim. (1975) 616) of isothiazole compounds of the general formula 7

in which R ¹ and R ^{2 have} the meaning described above.

Isothiazole compounds of general formula 7 are known and are prepared according to methods known from the literature (representative: A.D.N. NcGregor. U. Corbin, J.E. Swigor, I.C.

Cheney, Tetrahedron 25 (1968) 389; b. F. Lucchesini,

N. Picci. M. Pocci. Heterocycles 29 (1989) 97).

The synthesis of the isothiazolecarboxylic acid derivatives of the general formula 6b is carried out by reacting the isothiazole halogen compounds 3 with inorganic cyanides, such as, for example, copper (I) cyanide, by processes known from the literature (representative: A. Alberola, F. Alonso, P Cuadrado, MC Sanudo, J. Heterocyclic Chem. 25: 235 (1988). The corresponding isothiazolecarboxylic acid derivatives of the general formula 6a can be prepared starting from isothiazolecarboxylic acid derivatives of the general formula 6b using methods known from the literature.

Preferred organomagnesium compounds are alkylmagnesium halides, such as, for example, methyl or ethylmagnesium bromide or chloride. Preferred organolithium compounds are aliphatic lithium compounds, such as lithium diisopropylamide, n-butyl or secondary butyllithium. The organic solvent is selected depending on the starting materials used. In general, any inert solvent is suitable. Preferred inert solvents are aliphatic, cyclic or acyclic ethers, such as, for example, diethyl ether, tetrahydrofuran, dioxane or 1,2-dimethoxyethane. In addition, inert aromatic solvents, such as benzene or toluene, are also used.

The starting materials are usually reacted with one another in stoichiometric amounts. However, it may be advantageous, for example to increase the yield, to use one of the starting materials in an excess of 0.1 to 10 mol equivalents.

Benzoic acids of the formula 4 can be prepared as follows: benzoyl halides such as, for example, benzoyl chlorides of the formula 4

are made in a manner known per se by reacting the benzoic acids of the formula 4 made with thionyl chloride.

The benzoic acids of formula 4 *

can in a known manner by acid or basic hydrolysis from the corresponding esters of formula 4 / getting produced. Some of the intermediates of formula 4 are known or can be prepared by processes known from the literature.

Scheme 1

R ^{4 4}

Then arylthio compounds 8 with substituted haloalkenyl according to J. Med. Chem. 1984, 27, 1516, substituted alkynylcarboxylic acids according to J. Org. Chem. 1980, 45, 4611 or J. Am. Chem. Soc. 1983, 105, 883, substituted haloalkyl carboxylic acids according to Chem. Ber. 1925, 58, 1612 in the presence of a base such as alkali metal hydroxide, alkali metal hydroxide or alkali metal carbonate. The resulting compounds 9 are cyclized to 10 under Friedel-Crafts conditions with the addition of a Lewis acid or a protonic acid. AICI ₃ or SnCl ₄ are used as Lewis acids and polyphosphoric acid and sulfuric acid as protonic acid according to Can. J. Chem. 1981, 59, 199; Chem. Ber. 1925, 58, 1625; Chem. Ber. 1926, 59, 1074; Phosp. and sulf. 1984, 19, 31 preferred.

Thiochromenonic acids can still be obtained e.g. Elimination of hydrogen halide from 3-halothiochromanonic acids or e.g. by reacting the substituted thiophenolic acids with substituted α-alkylacetoacetic esters in the presence of phosphorus pentoxide according to Ann. Chem. 1964, 680, 40.

The arylthio compounds 8 can be obtained, for example, by a Sandmeyer reaction from corresponding anilines, which in turn are synthesized by reduction of suitable nitro compounds according to Organikum 19th edition 1992, 552ff.

In the event that, for example, A is (-CR ⁷ R ⁸ -) or (-CR ⁷ R ⁸ CR ⁹ R ¹⁰ -), B is C = O and R ¹⁸ is C ₁ -C ₄ alkoxy yourself the

Thiochromanone esters or dihydrobenzothiophene esters as described in Scheme 1 by alkylation of the arylthio compound 8 in counter were one of the above bases in solvent or water with halogen propionic acid or haloacetic acid and cyclize to 10. The reactants and the base are expediently used in equimolar amounts. The reaction mixture is preferably stirred at 20-100 ° C., in particular at 20-40 ° C. Working up is carried out, for example, by pouring the reaction mixture onto water, acidifying the aqueous phase with mineral acids such as hydrochloric acid or sulfuric acid and suctioning off the valuable product or extracting it by extraction with methylene chloride or ethyl acetate, drying and removing the solvent. The ester can be reacted without further purification.

By stirring 9 in, for example, polyphosphoric acid at 40-140 ° C, in particular at 70-100 ° C, or by activating the carboxylic acid by converting it into acid chloride and stirring with 2-6, in particular 3.5 to 4.5, molar equivalents of a Lewis acid such as, for example, AICI ₃ or SnCl ₄ in a solvent or by stirring with or in sulfuric acid, an intermediate stage of the formula 4 is obtained after known working up, ie adding ice water and suctioning off the product of value or extraction of the aqueous phase with ethyl acetate or methylene chloride, drying and removal of the solvent .

In the event that e.g. A is equal to an ethylene grouping

(-CR ⁷ = CR8-), B equals C = O and R ¹⁸ equals C ₁ -C ₄ alkoxy, the thiochromenone ester can be reacted, for example, by reacting an aryl thio compound with an acetylenecarboxylic acid derivative in water or solvent at a temperature of 0-140 ° C. Working up is carried out in a known manner by adding water and dilute mineral acid such as hydrochloric acid. The product of value is either suctioned off or obtained by extraction with methylene chloride or ethyl acetate, followed by drying and removal of the solvent.

The intermediates of formula 4 can be obtained by reactions known from the literature such as reduction according to Jerry March "Advanced Organic Chemistry, Fourth Ed., E.g. S.910ff, oximation according to Jerry March" Advanced Organic Chemistry, Fourth Ed., E.g. P.934, 935, 1039, 1226, 405ff, conversion into imines and amines according to Jerry March "Advanced Organic Chemistry, Fourth Ed., Ketalization,

Alkylation, halogenation, elimination and oxidation can be further functionalized according to Jerry March "Advanced Organic Chemistry, Fourth Ed. The acids of 3-alkoxy-1,2-benzisothiazol-1,1-dioxide or

3-alkoxy-1,2-benzisothiazoles can be obtained starting from corresponding saccharin derivatives or 1,2-benzisothiazoles by, for example, reaction with PCI ₅ , POCI ₃ or chlorine and alcohol, if appropriate in the presence of an auxiliary base such as, for example, triethylamine, which is described, for example, in US 4,571,429, Arch. Pharm. 1984, 317, 807, US 4461901, US 450916, J. Med. Chem. 1986, 29, 359.

Saccharin carboxylic acids can be described by literature methods according to Ann. Chem. 427, 231, 1922, Chem. Ber. 13, 1554, 1980,

Chem. Ber. 25, 1740, 1892, DE-OS 3607343, German patent application P 44 27 995.7 can be obtained.

The derivatives of benzo-1,4-oxathiic acids are partially known, e.g. from J. Org. Chem. 1968, 33, 456 or e.g.

by reaction from the corresponding phenol derivatives according to

Chem. Comm., 1975, 451, J. Org. Chem. 1974, 39, 1811, J. Am.

Chem. Soc. 1954, 76, 1068 or by combining e.g. Substitution reaction on halogen-substituted thiophenol derivatives and further reactions such as oxidation, reduction or addition according to J. Het. Chem. 1983, 20, 867.

The benzoic acids of formula 4 can also be obtained by using the corresponding bromo or iodo substituted compound of formula 11

R ¹⁸ OH, C ₁ -C ₄ alkoxy

A, B, R ⁴ , R ⁵ and R ^{6 have} the meaning described above in the presence of a palladium, nickel, cobalt or rhodium transition metal catalyst and a base with carbon monoxide and water under elevated pressure.

The catalysts nickel, cobalt, rhodium and in particular

Palladium can be metallic or in the form of customary salts, such as in the form of halogen compounds, for example PdCl _2, RhCl ₃ · H ₂ O, acetates, eg Pd (OAc) _2, cyanides and the like at the known valency states. Furthermore, metal complexes with tertiary phosphines, Metal alkylcarbonyls, metal carbonyls, for example CO ₂ (CO) ₈ , Ni (CO) ₄ , metal carbonyl complexes with tertiary phosphines, for example

(PPh ₃ ) ₂ Ni (CO) ₂ , or transition metal salts complexed with tertiary phosphines. The latter embodiment is particularly preferred in the case of palladium as a catalyst. The type of phosphine ligand is widely variable. For example, they can be represented by the following formulas:

where n denotes the numbers 1, 2, 3 or 4 and the radicals up to R ¹⁹ for R ^{22 are} low molecular weight alkyl, for example C ₁ -C ₆ alkyl, aryl,

C ₁ -C ₄ alkylaryl, for example benzyl, phenethyl or aryloxy.

Aryl is, for example, naphthyl, anthryl and preferably optionally substituted phenyl, the substituents only having to be considered for their inertness to the carboxylation reaction, otherwise they can be varied widely and include all inert C-organic radicals such as C ₁ -C ₆ -alkyl radicals , e.g. methyl, carboxyl residues such as COOH, COOM (M is for example a

Alkali, alkaline earth metal or ammonium salt), or C-organic radicals bound via oxygen, such as C ₁ -C ₆ alkoxy radicals.

The phosphine complexes can be prepared in a known manner, for example as described in the documents mentioned at the outset. For example, customary commercially available metal salts such as PdCl ₂ or Pd (OCOCH ₃ ) _{2 are used} and the phosphine is added, for example P (C ₆ H ₅ ) ₃ , P (nC ₄ H ₉ ) ₃ , PCH ₃ (C ₆ H ₅ ) ₂ , 1,2-bis (diphenylphosphino) ethane.

The amount of phosphine, based on the transition metal, is usually 0 to 20, in particular 0.1 to 10 molar equivalents, particularly preferably 1 to 5 molar equivalents. The amount of transition metal is not critical. Of course, for reasons of cost, you will rather get a small amount, e.g. from 0.1 to 10 mol%, in particular 1 to 5 mol%, based on the starting material 3 or 4. For the preparation of the benzoic acids 4

0 one carries out the reaction with carbon monoxide and at least

equimolar amounts of water, based on the starting materials 10 by. The reactant water can also serve as a solvent, i.e. the maximum amount is not critical.

However, depending on the type of starting materials and the catalysts used, it may also be advantageous to use another inert solvent instead of the reaction partner or those for

Carboxylation used base to use as a solvent.

Suitable inert solvents for carboxylation reactions are solvents such as hydrocarbons, e.g. Toluene, xylene, hexane, pentane, cyclohexane, ether e.g. Methyl tert-butyl ether, tetrahydrofuran, dioxane, dimethoxyethane, substituted amides such as dimethylformamide, per-substituted ureas such as

Tetra-C ₁ -C ₄ alkylureas or nitriles such as benzonitrile

or acetonitrile.

In a preferred embodiment of the process, one of the reactants, in particular the base, is used in excess, so that no additional solvent is required.

Bases suitable for the process are all inert bases which are able to bind the hydrogen iodide or bromine hydrogen released during the reaction. Examples here are tertiary amines such as tert-alkylamines, for example trialkylamines such as triethylamine, cyclic amines such as N-methylpiperidine or N, N'-dimethylpiperazine, pyridine, alkali metal or hydrogen carbonates, or tetraalkyl-substituted urea derivatives such as tetra-C ₁ -C ₄ alkyl urea, for example tetramethyl urea.

The amount of base is not critical, usually 1 to 10, in particular 1 to 5, moles are used. When the base is simultaneously used as a solvent, the amount is generally such that the reactants are dissolved, unnecessarily high excesses being avoided for reasons of practicality in order to save costs, to be able to use small reaction vessels and to ensure maximum contact for the reactants. During the reaction, the carbon monoxide pressure is adjusted so that there is always an excess of CO, based on 10. The carbon monoxide pressure at room temperature is preferably 1 to 250 bar, in particular 5 to 150 bar CO. The carbonylation is generally carried out continuously or batchwise at temperatures from 20 to 250 ° C., in particular at 30 to 150 ° C. With discontinuous operation expediently continuously pressed carbon monoxide onto the reaction mixture to maintain a constant pressure. The aryl halogen compounds 11 used as starting compounds are known or can easily be prepared by a suitable combination of known syntheses and reaction sequences described above. Examples of particularly preferred compounds of general formula 1 are compiled in the following tables. The definitions of the residues are not only particularly preferred in the specific combination of residues, but are also considered in isolation.

The compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides. The herbicidal compositions containing I control vegetation very well on non-cultivated areas, particularly when high amounts are applied. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates.

Depending on the particular application method, the compounds I or compositions containing them can also be used in a further number of crop plants for eliminating undesired plants. The following crops are considered, for example:

Allium cepa, pineapple comosus, Arachis hypogaea, asparagus

officinalis, Beta vulgaris spec. altissima, Beta vulgaris rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora), Coffucumiberis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum batgatus, Iumomo lupusas, Humulus culinaris, linum

usitatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Musa spec, Nicotiana tabacum (N.ru- stica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus av , Prunus persica, Pyrus communis, Ribes sylestre, Ricinus coπvmunis, Saccharum officinarum, Seeale cereale, Solanum tuberosum, Sorghum bicolor (see vulgar), Theobroma cacao, Trifolium pratense,

Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.

In addition, the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.

The herbicidal compositions or the active compounds can be applied pre- or post-emergence. If the active ingredients are less compatible for certain crop plants, application techniques can be used in which the

Herbicidal agents are sprayed with the aid of sprayers so that the leaves of the sensitive crops if possible not be hit while the active ingredients get on the leaves of unwanted plants growing underneath or the uncovered floor area (post-directed, lay-by). The compounds I or the herbicidal compositions comprising them can be sprayed, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, and also high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, spreading agents or granules , Atomizing, dusting, scattering or pouring can be used. The application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention. The following are essentially considered as inert additives:

Mineral oil fractions from medium to high boiling point, such as kerosene or diesel oil, also coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol, cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, e.g. B. amines such as N-methylpyrrolidone or water. Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. For the production of emulsions, pastes or oil dispersions

Substrates as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. However, it is also possible to prepare concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.

The surface-active substances (adjuvants) are the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts sulfated hexa-, hepta- and octadecanols as well as fatty alcohol glycol ether, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl, phenyl or nonyl phenyl or phenyl Tributylphenyl polyglycol ether, alkyl aryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene alkyl ether, lauryl alcohol polyglycol ether acetate, sorbitol ester, lignin sulfite liquor or methyl cellulose.

Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier. Granules, e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers. Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Urea and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid

Carriers.

The concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range. The formulations generally contain 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

The connection 28 according to the invention can be formulated, for example, as follows:

I. 20 parts by weight of compound 28 are dissolved in a mixture consisting of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and

5 parts by weight of the adduct of 40 moles

There is ethylene oxide in 1 mol of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.

II. 20 parts by weight of compound 28 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30

Parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide in 1 mol of castor oil. Through a pouring and finely distributing the solution in 100,000 parts by weight of water gives an aqueous dispersion which contains 0.02% by weight of the active ingredient. III. 20 parts by weight of active ingredient 28 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65

Parts by weight of a mineral oil fraction from the boiling point 210 to 280 ° C and 10 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil. By pouring the solution into 100,000

Parts by weight of water give an aqueous dispersion which contains 0.02% by weight of the active ingredient.

IV. 20 parts by weight of active ingredient 28 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene sulfonic acid, 17 parts by weight of the sodium salt of lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill. By finely distributing the mixture in 20,000 parts by weight of water, a spray liquor is obtained which contains 0.1% by weight of the active ingredient.

V. 3 parts by weight of active ingredient 28 are mixed with 97 parts by weight of finely divided kaolin. In this way a dust is obtained which contains 3% by weight of the active ingredient.

VI. 20 parts by weight of active ingredient 28 are mixed with 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8

Parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a phenol-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained.

VII. 1 part by weight of compound 28 is dissolved in a mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. A stable emulsion concentrate is obtained.

VIII. 1 part by weight of compound 28 is dissolved in a mixture consisting of 80 parts by weight of cyclohexanone and 20

Parts by weight of Emulphor EL (ethoxylated castor oil / casteroil). A stable emulsion concentrate is obtained. To broaden the spectrum of activity and to achieve synergistic effects, the heterocyclic-fused benzoylisothiazoles I can be mixed with numerous representatives of other herbicidal or growth-regulating active ingredient groups and applied together. For example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and their derivatives, aminotriazoles, anilides, (het) -aryloxyalkanoic acid and their derivatives, benzoic acid and their derivatives, benzothiadiazinones, 2-aroyl come as mixing partners -1,3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinoline carboxylic acids and their derivatives, chloroacetanilides, cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid and their derivatives, dihydrobenzofuranane -ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,

Oxadiazoles, oxiranes, phenols, aryloxy- or heteroaryloxyphenoxypropionic acid esters, phenylacetic acid and its derivatives, phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles,

Pyridazines, pyridinecarboxylic acid and their derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides, uraciles.

It may also be useful to apply the compounds I alone or in combination with other herbicides, mixed with other crop protection agents,

for example with means for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are used to remedy nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added.

Depending on the control target, the season, the target plants and the growth stage, the active compound application rates are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (see also)

Synthesis examples

Synthesis of 4- (2 ', 4'-dimethyl-5'-saccharinoyl) -5-cyclopropylisothiazole 28

The following operations are carried out in the absence of moisture. 9.0 g (0.04 mol) of 4-iodo-5-cyclopropylisothiazole in 200 ml are added to 60 ml of a 1.4 M solution of (0.08 mol) of methyl magnesium bromide in toluene / tetrahydrofuran 3: 1 (v / v) Tetrahydrofuran added with ice cooling so that the reaction temperature does not exceed 5 ° C. The reaction mixture is mixed with a Solution of 21.9 g (0.08 mol) of 2,4-dimethylsaccharin-5-carboxylic acid chloride in 300 ml of tetrahydrofuran. After the exothermic reaction has subsided, residues of organometallic compounds are hydrolyzed with 100 ml of 10% hydrochloric acid. The reaction mixture is taken up in diethyl ether, worked up with water, dried with sodium sulfate, filtered and i. Vac. freed from the solvent. The crude product is purified on 250 g of silica gel with mixtures of cyclohexane / ethyl acetate 10: 1 to 4: 1 (v / v). Yield. 5.2 g (36%) colorless solid, 270 MHz ¹ H-NMR

(CDCl ₃ ), δ [ppm]: 1.0 (m, 2 H), 1.4 (m, 2 H), 2.8 (s, 3 H), 3.0 (m, 1 H), 3.3 (s, 3H), 7.8 (d, 1H), 7.9 (d, 1H), 8.3 (s, 1H).

The herbicidal activity of the heterocyclically fused benzoylisothiazoles of the formula I was demonstrated by greenhouse experiments:

Plastic flower pots with loamy sand with about 3.0% humus as substrate served as culture vessels. The seeds of the test plants were sown separately according to species.

In pre-emergence treatment, the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles. The tubes were lightly sprinkled to promote germination and growth, and then covered with clear plastic hoods until the plants had grown. This cover causes the test to germinate evenly plant, unless this was affected by the active ingredients.

For the purpose of post-emergence treatment, the test plants, depending on the growth habit, are first grown to a height of 3 to 15 cm and only then treated with the active ingredients suspended or emulsified in water. The test plants are either sown directly and grown in the same containers, or they are first grown separately as seedlings and transplanted into the test containers a few days before the treatment.

The application rate for post-emergence treatment 0.5 or 0.25 kg / ha a.S. The plants were kept at temperatures of 10 - 25 ° C or 20 - 35 ° C depending on the species. The trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.

It was rated on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal

Growth course.

The plants used in the greenhouse experiments are composed of the following types:

Latin name German name English name

Chenopodium album White Goosefoot lambsquarters

(goosefoot)

Echinochloa crus-galli millet barnyardgrass

Sinapis album Weißer Senf white mustard

Solanum nigrum Black night black nightshade

shadow

Claims

claims

1. 4-benzoylisothiazoles of the general formula 1

in which the substituents have the following meaning: X is oxygen or sulfur;

R ^{1 is} hydrogen, alkyl, alkenyl, alkynyl; if necessary subst.

Alkoxycarbonyl;

if necessary subst. Aryl, if necessary subst. Heterocyclyl or subst. Hetaryl;

R ^{2 is} hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, it being possible for these radicals to carry one or more of the following groups: halogen, alkyl,

Alkenyl or alkynyl;

Aryl, which radical can carry one or more of the following groups:

Alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio or alkenylthio, where these radicals can be partially or completely halogenated or can carry one or more of the following groups: alkoxy, alkenyloxy, aryloxy, alkylsulfonyl, alkenylsulfonyl or arylsulfonyl;

Alkylsulfonyl or alkoxycarbonyl;

if necessary subst. Aryloxy or optionally subst. Arylthio; if necessary subst. Mono- or dialkylamino, optionally subst.

Mono- or diarylamino or optionally subst. N-alkyl-N-arylamino, where alkyl and aryl can be the same or different;

Halogen, cyano or nitro;

Alkyl, alkoxy or aryl and in the case of hetero cyclyl can carry at least one of the nitrogen in one of the following groups:

Alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, haloalkoxy, optionally subst. Aryl or optionally subst. Aryloxy; R ^{3 is} a radical of the general formula 2a-d

" in which n, A, B and the substituents R ⁴ , R ⁵ and R ^{6 have the} following meaning: n zero, one or two A a chain (-CR ⁷ R ⁸ -), (-CR ⁷ R ⁸ -CR ⁹ R ¹⁰ -),

(-CR ⁷ = CR ⁸ -), (-CR ⁷ R ⁸ -CR ⁷ = CR ⁸ -) or one

Nitrogen atom, which in turn can be substituted by a substituent selected from the group consisting of hydrogen, alkyl, alkenyl, optionally subst. Aryl or arylalkyl, alkoxy, halogen,

Haloalkyl or haloalkoxy;

B is a group consisting of C = O, C = NR ¹¹ ,

CR ¹² -NR ¹³ R ¹⁴ , CR ¹² -OR ¹⁵ , CR ¹⁶ R ¹⁷ , CR ¹² -SR ¹⁵ , with hydrogen or alkyl subst. 1,3-dioxanyl or 1,3-dioxolanyl, a heteroatom selected from the group consisting of oxygen, sulfur or Nitrogen, where the nitrogen can in turn be substituted by a substituent selected from the group hydrogen, alkyl, alkenyl, optionally subst. Aryl or arylalkyl, alkoxy, halogen, haloalkyl or haloalkoxy, the bond between A and B can be saturated or unsaturated, R ⁴ -R ⁶ can be identical or different and independently of one another represent hydrogen, alkyl, alkenyl,

Alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, hydroxy, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkylalkoxy, cycloalkylalkenyloxy, cycloalkylalkynyloxy, aryloxyoxy, cycloalkenyloxyoxy, cycloalkenyloxyoxy, cycloalkenyloxyoxy, cycloalkenyloxyoxy, cycloalkenyloxyoxy, cycloalkenyloxyoxy, cycloalkenyloxyoxy, cycloalkenyloxyoxy, cycloalkenyloxyoxy, cycloalkenyloxyoxy, cycloalkenyloxyoxy, cycloalkenyloxyoxy, cycloalkenyloxyoxy, cycloalkenyloxy, cycloalkoxy Alkenylthio, alkynylthio, cycloalkylthio, cycloalkylalkylthio, cycloalkylalkenylthio, cycloalkylalkynylthio, cycloalkenylthio, arylthio, arylalkylthio, arylalkenylthio, arylalkynylthio, amino, optionally subst. Mono- or dialkylamino, optionally subst. Mono or diarylamino, if necessary subst. N-alkyl-N-arylamino, where alkyl and aryl can be the same or different, alkenylamino, alkynylamino, cycloalkylamino, cycloalkenylamino, sulfonyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, cycloalkylalkylsulfonyl, cycloalkylalkenylsulfonyl, cycloalkylalkenylsulfonylsulfonyl Sulfoxyl, alkyl sulfoxyl,

Alkenyl sulfoxyl, alkynyl sulfoxyl, cycloalkyl sulfoxyl, cycloalkylalkyl sulfoxyl, cycloalkylalkenyl sulfoxyl, cycloalkylalkynyl sulfoxyl, aryl sulfoxyl, arylalkyl sulfoxyl, arylalkenyl sulfoxyl, arylalkynyl sulfoxyl, aminosulfonyl, optionally subst. Mono- or dialkylaminosulfonyl, optionally subst. Mono- or diarylaminosulfonyl, optionally subst. N-alkyl-N-arylaminosulfonyl, where alkyl and aryl can be the same or different, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, cycloalkylalkylcarbonyl, cycloalkylalkenylcarbonyl, cycloalkylalkynylcarbonyl, arylcarbonyl, arylalkylcarbonyl, arylalkenylcarbonyl, arylalkynylcarbonyl,

Carboxyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkylalkenyloxycarbonyl, cycloalkylalkynyloxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl, arylalkenyloxycarbonyl, arylalkynyloxycarbonyl, amino carbonyl, optionally subst. Mono- or dialkylaminocarbonyl, optionally subst. Mono- or diarylaminocarbonyl, optionally subst. N-alkyl-N-arylaminocarbonyl, where alkyl and aryl can be the same or different, optionally subst.

Mono- or dialkylcarbonylamino, optionally subst. Mono or

Diarylcarbonylamino, optionally subst. N-alkyl-N-arylcarbonylamino, where alkyl and aryl may be the same or different, alkoxyaminocarbonyl, alkenyloxycarbonylamino, alkynyloxycarbonylamino, cycloalkoxycarbonylamino, cycloalkylalkoxycarbonylamino, cycloalkylalkenylyloxycarbonylamino, cycloalkylalkynyloxycarbonylyloxyaminoylaminoylaminoylaminoylaminoylaminoylaminoylaminoylaminoylaminoylaminoylaminoylamino haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy, haloalkenyloxy, Haloalkinyloxy haloalkylthio, Haloalke- nylthio, Haloalkinylthio, Haloalkylamino, Haloalkenylamino, Haloalkinylamino, haloalkylsulfonyl, Haloalkenylsulfonyl, Haloalkinylsulfonyl, Haloalkylsulfoxyl, Haloalkenylsulfoxyl, Haloalkinylsulfoxyl, Haloalkylcarbo- nyl, Haloalkenylcarbonyl, Haloalkinylcarbonyl, Haloal- koxycarbonyl, Haloalkenyloxycarbonyl , Haloalkynyloxycarbonyl, haloalkylamimocarbonyl, haloalkenylaminocarbonyl, haloalkynylaminocarbonyl, haloalkoxycarbonylamino, haloalkenyloxycarbonylamino, haloalkynyloxycarbonyl amino; Cyano or nitro; or one of the following

Groups:

>

R ⁷ , R ⁸ independently of one another are hydrogen, alkyl, haloalkyl,

Alkoxy, haloalkoxy; if necessary subst. Phenyl, where the substituents can consist of alkyl, alkoxy, haloalkoxy, haloalkyl, halogen, cyano, nitro;

R ^{9 is} hydrogen, alkyl, haloalkyl, alkoxy, C ₁ -C ₆ haloalkoxy; if necessary subst. Phenyl, where the substituents can consist of alkyl, alkoxy, haloalkoxy, haloalkyl, halogen, cyano, nitro;

R ^{10 is} hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy;

if necessary subst. Phenyl, where the substituents can consist of alkyl, alkoxy, haloalkoxy, haloalkyl, halogen, cyano, nitro; R ¹¹ hydrogen, amino, optionally subst. Mono- or dialkylamino or N-alkyl-N-arylamino, where alkyl and aryl can be the same or different, alkyl, haloalkyl, alkoxy, haloalkoxy, alkenyl, haloalkenyl, alkynyl;

if necessary subst. Phenyl, where the substituents can consist of alkyl, alkoxy, haloalkoxy, haloalkyl, halogen, cyano, nitro; if necessary subst. Benzyl, where the substituents can consist of alkyl, alkoxy, haloalkoxy, haloalkyl, halogen, cyano, nitro; if necessary subst. Benzyloxy where the substituents can consist of alkyl, alkoxy, haloalkoxy, haloalkyl, halogen, cyano, nitro; R ^{12 is} hydrogen, alkyl, alkoxy, haloalkyl, haloalkoxy;

if necessary subst. Phenyl, where the substituents can consist of one to three halogens, alkyl, alkoxy, haloalkoxy, nitro; R ¹² and R ⁹ or R ¹² and R ⁷ can form a bond;

R ¹³ , R ¹⁴ independently of one another are hydrogen, alkyl, alkenyl,

Haloalkyl, haloalkenyl, alkoxy, haloalkoxy; if necessary subst. Phenyl, where the substituents can consist of alkyl, alkoxy, haloalkoxy, haloalkyl, halogen, cyano, nitro;

if necessary subst. Benzyl, where the substituents can consist of alkyl, alkoxy, haloalkoxy, haloalkyl, halogen, cyano, nitro; R ^{15 is} hydrogen, alkyl, haloalkyl, optionally subst. Phenyl, where the substituents can consist of alkyl, alkoxy, haloalkoxy, haloalkyl, halogen, cyano, nitro;

if necessary subst. Benzyl, where the substituents can consist of alkyl, alkoxy, haloalkoxy, haloalkyl, halogen, cyano, nitro; R ¹⁶ , R ¹⁷ independently of one another hydrogen, alkyl; possibly.

subst. Phenyl, where the substituents can consist of one to three halogens, alkyl, alkoxy, haloalkoxy, nitro; R ¹⁶ and R ⁷ or R ¹⁶ and R ⁹ can form a formation; as well as customary salts of 4-benzoylisothiazoles of the general formula 1.

2. 4-benzoylisothiazoles of the general formula 1 according to claim 1, in which X is oxygen.

3. 4-benzoylisothiazoles of the general formula 1 according to claim 1 or 2, in which R ^{1 is} hydrogen or optionally subst. Alkoxycarbonyl means.

4. 4-benzoylisothiazoles of the general formula 1 according to one of claims 1 to 3, in which R ^{2 is} alkyl, cycloalkyl, aryl, which can be substituted one or more times by halogen or haloalkyl, or hetaryl, which can be substituted once or more by halogen can.

5. 4-benzoylisothiazoles of the general formula 1 according to one of claims 1 to 4, in which R ^{2 is} methyl, ethyl, isopropyl, tert. Butyl, cyclopropyl, 1-methylcyclopropyl, 3-trifluoromethylaryl, 2,4-difluoroaryl, 1,3-benzodioxolyl, 2,2-difluoro-1,3-benzodixolyl, 1,3-benzoxathiolyl,

3,3-dioxo-1,3-benzoxathiolyl, benzoxazolyl, pyrazolyl or thienyl.

6. 4-benzoylisothiazoles of the general formula 1 according to claims 1 to 5, in which R ³ for a radical of the general formula 2b or 2d

stands .

7. 4-benzoylisothiazoles of the general formula 1 according to one of claims 1 to 6, in which R3 for a radical of the general formula 2b or 2d

is in which the substituents R ⁴ -R ^{6 have} the following meaning:

R ⁴ -R ⁶ may be the same or different and are independently hydrogen, alkyl, cycloalkyl, aryl, hydroxy, alkoxy, cycloalkoxy, aryloxy, thio, alkylthio, cycloalkylthio, arylthio, amino, optionally subst. Mono- or dialkylamino or mono- or diarylamino or N-alkyl-N-arylamino, where alkyl and aryl can be the same or different, cycloalkylamino, sulfonyl, alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, sulfoxyl, alkylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, alkylcarbonyl, Cycloalkylcarbonyl, arylcarbonyl, carboxyl, alkoxycarbonyl, cycloalkoxycarbonyl, aryloxycarbonyl, aminocarbonyl, optionally subst. Mono- or dialkylaminocarbonyl or mono- or diarylaminocarbonyl or N-alkyl-N-arylaminocarbonyl, where alkyl and aryl may be the same or different, alkoxyaminocarbonyl, cycloalkoxycarbonylamino, aryloxycarbonylamino, halogen, haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfon, haloalkylsulfon, haloalkylsulfon, haloalkylsulfon Haloalkylcarbonyl, Haloalkoxycarbonyl, Haloalkylamimocarbonyl, Haloalkoxycarbonylamino, Cyano or

Nitro.

8. 4-benzoylisothiazoles of the general formula 1 according to claims 1 to 5, in which R ³ for a radical of the general formula 2b or 2d

stands, wherein R ⁴ , R ⁵ and R ^{6 have} the following meaning:

R ⁴ -R ⁶ can be the same or different and independently of one another represent a low molecular weight radical selected from the group hydrogen, alkyl,

Hydroxy, alkoxy, sulfonyl, sulfonylalkyl, halogen,

Haloalkyl, cyano or nitro.

9. 4-benzoylisothiazoles of the general formula 1 according to claim 1, in which R ³ for a radical of the general formula 2e

in which R ⁵ and R ^{6 represent} hydrogen, alkyl, alkenyl, alkynyl, alkoxy, haloalkyl, haloalkoxy, halogen, nitro or cyano and R ^{4 represents} hydrogen, alkyl, alkenyl, alkynyl,

Alkoxy, haloalkyl, C ₁ -C ₄ haloalkoxy, halogen, nitro or cyano and n, B, R ⁷ , R ⁸ , R ⁹ and R ^{10 have} the meanings given in Claim 1.

10. 4-benzoylisothiazoles of the general formula 1 according to claim 1, in which R ³ for a radical of the general formula 2f

in which R ⁵ and R ^{6 represent} hydrogen, alkyl, alkenyl,

Alkynyl, alkoxy, haloalkyl, haloalkoxy, halogen, nitro or cyano and R ⁴ for hydrogen, alkyl, alkenyl, alkynyl, Alkoxy, haloalkyl, haloalkoxy, halogen, nitro or cyano and n, B, R ⁷ and R ^{8 have} the meanings given in claim 1.

11. 4-benzoylisothiazoles of the general formula 1 according to claim 1, in which R ³ for a radical of the general formula 2g

in which R ⁴ and R ^{5 are} hydrogen, alkyl, alkenyl,

Alkynyl, alkoxy, haloalkyl, haloalkoxy, halogen nitro or cyano and R ⁴ for hydrogen, alkyl, alkenyl, alkynyl,

Alkoxy, haloalkyl, haloalkoxy, halogen nitro or cyano and n, B, R ⁷ and R ^{8 have} the meanings given in claim 1.

12. 4-benzoylisothiazoles of the general formula 1 according to claim 1, in which R ³ for a radical of the general formula 2a-d

2c 2d in which n is one or two and B is CR ¹² -OR ¹⁵ , where R ¹² and R ^{15 have} the meaning given in claim 1.

13. 4-benzoylisothiazoles of the general formula 1 according to claims 1 to 5, in which R ^{3 is} a radical of the general formula 2b or 2d

in which n, B, R ⁴ , R ⁵ and R ^{6 have} the meaning given in claim 1 and A represents a nitrogen atom which in turn can be substituted by hydrogen, alkyl,

Alkenyl, if necessary subst. Aryl or arylalkyl, alkoxy, halogen, haloalkyl or haloalkoxy.

14. 4-benzoylisothiazoles of the general formula 1 according to claims 1 to 5, in which R ^{3 is} a radical of the general formula 2b or 2d

in which n, R ⁴ , R ⁵ and R ^{6 have} the meaning given in Claim 1 and A represents a nitrogen atom which can in turn be substituted by hydrogen, alkyl, Alkenyl, if necessary subst. Aryl or arylalkyl, alkoxy, halogen, haloalkyl or haloalkoxy and BC = O means.

15. A process for the preparation of the 4-benzoylisothiazoles of the general formula 1 according to claim 1, characterized in that an isothiazole halogen compound of the general formula 3

in which Y is halogen, with elemental magnesium, an organomagnesium compound or an organolithium compound and a carboxylic acid derivative of the general formula 4,

in which R ¹⁸ denotes halogen, N-alkoxy-N-alkylamino or cyano in the presence of an inert solvent in one

Temperature range from -78 ° C to 111 ° C implemented with each other.

16. A process for the preparation of the 4-benzoylisothiazoles of the general formula 1 according to claim 1, characterized in that a halogenobenzene of the general formula 5 in the Y represents halogen with elemental magnesium, an organomagnesium or an organolithium compound and an isothiazolecarboxylic acid derivative of the general formula 6a or 6b, in which R ¹⁸ denotes halogen or N-alkoxy-N-alkylamino in the presence of an inert solvent in a temperature range from -78 ° C. to 111 ° C.

17. Herbicidal compositions which contain a 4-benzoylisothiazole of the general formula 1 according to claim 1 and inert additives.

18. A method of combating undesirable plant growth, characterized in that the undesirable plants and / or their habitat are treated with a herbicidally active amount of a 4-benzoylisothiazole of the general formula 1 according to claim 1.