DE19929259A1 - New cyclohexanone derivatives of bicyclic benzoic acids useful as herbicides - Google Patents

Abstract

Cyclohexanone derivatives of bicyclic benzoic acids (I) are new Cyclohexanone derivatives of bicyclic benzoic acids of formula (I) and their salts are new. X = O, S, SO, SO2, NR<1> or NR<1>R<17>; R<1> = H, 1-6C (halo)alkyl, (halo)alkoxy, (halo)alkyl sulfonyl or (halo)alkyl carbonyl, 1-6C alkoxy-1-6C alkyl, 1-6C alkylcarbonyl-1-6C alkyl(carbonyl), 1-6C alkylcarbonyloxy-1-6C alkyl, 3-6C cycloalkyl(carbonyl), 3-6C cycloalkoxy, 3-6C cycloalkyl(carbonyl(oxy))-1-6C alkyl, 3-6C cycloalkoxy(carbonyl(oxy))-1-6C alkyl, 3-6C cycloalkyl sulfonyl, phenyl(sulfonyl), phenyl carbonyl, phenyl-1-6C alkyl(carbonyl), phenyl(oxy)carbonyl-1-6C alkyl, phenoxy-1-6C alkyl, phenylcarbonyloxy-1-6C alkyl, heterocyclyl(-1-6C alkyl), heterocyclylsulfonyl, heterocyclylcarbonyl(oxy)-1-6C alkyl or heterocyclylcarbonyl(1-6C alkyl), where the phenyl, heterocyclyl or cycloalkyl can be substituted by 1-4C (halo)alkyl, (halo)alkoxy, (halo)alkyl carbonyl or (halo)alkyl sulfonyl, nitro, hydroxy or cyano and/or are halogenated; R<2> = halo, 1-6C (halo)alkylthio, (halo)alkylsulfinyl or (halo)alkylsulfonyl; R<3> = H, halo or 1-6C (halo)alkyl; Hex = substituted (3-oxo-1 -cyclohexene-2-yl)carbonyl of formula (i), substituted (1,3-dioxo-2-cyclohexyl)methylidene of formula (ii); or 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-dithian-2-yl (all optionally substituted with 1-3 1-4C alkyl); R<4> = OH, SH, halo, OR<11>, SR<11>, SOR<12>, SO2R<12>, OSO2R<12>, P(O)R<13>R<14>, OP(O)R<13>R<14>, P(S)R<13>R<14>, OP(S)R<13>R<14>, NR<15>R<16>, ONR<15>R<16>, N-bound heterocycle optionally halogenated and/or substituted by 1-3 NO2, CN or 1-4C (halo)alkyl or (halo)alkoxy; R<5>, R<9> = H or 1-4C alkyl or alkoxycarbonyl; R<6>, R<8>, R<10> = H or 1-4C alkyl; or R<6> + R<8>, R<8> + R<10> = a bond or 1-5C alkyl (optionally substituted with 2 or 3 halo, CN, 1-4C (halo)alkyl or alkoxycarbonyl); or R<6> + R<10> = 1-4C alkyl (optionally substituted with 2 or 3 halo, CN or 1-4C (halo)alkyl or alkoxycarbonyl); R<7> = H, OH, halo, 1-6C (halo)alkyl, (halo)alkoxy, (halo)alkylthio, (halo)alkylsulfinyl, (halo)alkylsulfonyl or (halo)alkoxycarbonyl, di-(1-6C alkoxy)methyl, (1-6C alkoxy)-(1-6C alkylthio)-methyl or di(1-6C alkylthio)methyl; or R<7> + R<8> = O(CH)2)pO, O(CH2)pS, S(CH2)pS, O(CH2)q or S(CH2)q (optionally substituted with 1-3 of halo, CN or 1-4C (halo)alkyl or alkoxycarbonyl); or carbonyl; p = 2-5; q = 2-6; R<11> = 1-6C alkyl(carbonyl), alkylthiocarbonyl or alkylaminocarbonyl, 3-6C (halo)alkenyl, (halo)alkynyl, cycloalkyl(carbonyl), alkenyloxycarbonyl, alkylnyloxycarbonyl, alkenylaminocarbonyl or alkynylaminocarbonyl-2-6C alkenylcarbonyl or alkylnylcarbonyl, N,N-di(1-6C alkyl)amino(thio)carbonyl, N-(3-6C alkenyl)-N-(1-6C alkyl)-aminocarbonyl, N-(3-6C alkynyl)-N-(1-6C alkyl)aminocarbonyl, N-(1-6C alkoxy)-N-(1-6C alkyl)aminocarbonyl, , N-(3-6C alkenyl)-N-(1-6C alkoxy)aminocarbonyl, N-(3-6C alkynyl)-N-(1-6C alkoxy)aminocarbonyl or 2-6C alkoxyimino-1-6C alkyl, the (cyclo)alkyl or alkoxy optionally having 2 or 3 of CN, 1-4C alkoxy, alkylthio, alkylcarbonyl or alkoxycarbonyl, di-(1-4C alkyl)amino(carbonyl), 1-4C alkoxy-1-4C alkoxycarbonyl, hydroxycarbonyl, 1-4C alkylaminocarbonyl, aminocarbonyl, 1-4C alkylcarbonyloxy or 3-6C cycloalkyl, phenyl(1-6C alkyl), phenyl(amino)carbonyl, phenoxy(thio)carbonyl, phenylcarbonyloxy-1-6C alkyl, N-(1-6C alkyl)-N-phenylaminocarbonyl, phenyl-2-6C alkenylcarbonyl, heterocyclyl(-1-6C alkyl), heterocyclylcarbonyl, heterocyclyloxy(thio)carbonyl, N-(1-6C alkyl)-N-heterocyclylaminocarbonyl or heterocyclyl-1-6C alkenylcarbonyl, where the phenyl or heterocyclyl can be substituted by NO2, CN, 1-4C (halo)alkyl or (halo)alkoxy; R<12> = 1-6C (halo)alkyl or 1-4C (halo)alkoxy optionally halogenated and/or with 2 or 3 of CN, 1-4C (halo)alkoxy, (halo)alkylthio, alkyl carbonyl or (halo)alkoxycarbonyl, phenyl(1-4C alkyl) or heterocyclyl(1-4C alkyl), the phenyl or heterocycle being optionally halogenated and/or with 2 or 3 of NO2, CN, 1-4C (halo)alkyl, (halo)alkoxy or alkyl carbonyl; R<13>, R<14> = phenyl(1-4C alkyl), phenoxy (both optionally halogenated and/or optionally substituted with 2 or 3 of NO2, CN, 1-4C (halo)alkyl, (halo)alkoxy or alkyl carbonyl), H, 1-6C alkyl(thio) or alkoxy; R<15> = H, 1-6C alkyl(carbonyl), alkoxy or alkylcarbonylamino, 3-6C (halo)alkenyl, cycloalkyl, alkenyloxy, alkynyloxy or (halo)alkynyl, amino, OH or di(1-6C alkyl)amino (the (cycloalkyl) or alkoxy being optionally halogenated and/or optionally substituted with 1-3 of CN, 1-4C alkoxycarbonyl or alkylaminocarbonyl, di-(1-4C alkyl)aminocarbonyl or 3-6C cycloalkyl), phenyl(1-4C alkyl), phenylcarbonyl, heterocyclyl(1-4C alkyl) or heterocyclylcarbonyl (the phenyl and heterocyclyl being optionally halogenated and/or optionally substituted with 1-3 of NO2, CN, 1-4C (halo)alkyl or (halo)alkoxy); and R<16>, R<17> = H, 1-6C alkyl or 3-6C alkenyl or alkynyl. An Independent claim is included for compounds as above but where Hex is replaced by COOH.

Description

The present invention relates to cyclohexenone derivatives of bi cyclic benzoic acids which fused in the 2,3-position, have saturated heterocycle, process for their preparation such cyclohexenone derivatives, agents containing such a compound dungen contain, and the use of cyclohexenone derivatives or agents containing them for controlling harmful plants.

From WO 97/09324 cyclohexane-1,3-diones are herbicidal Kung known that a benzo-condensed in the 2-position Sulfur heterocycle, e.g. B. a thiochroman or a benzo have dihydrothiophene radical, which ge via a carbonyl group is bound.

Herbicides are known from WO 97/08164 which contain a cyclohexene have nonrest in the 2-position with a bicyclic Arylcarbonylrest is substituted. As examples of aryl carbo nyl residues are benzocondensed lactones such as benzfuranone, benzo pyranone, lactams such as benzopyrrolidone and benzopyrimidone, 2,3-benzo-4,5-dihydrothiophene dioxide and 2,3-beno-4,5,6,7-tetrahy called drothiepindioxid.

The herbicidal properties of those from the publications mentioned known compounds and their tolerances However, cultivated plants can only meet the requirements to a limited extent To satisfy herbicides.

The present invention is therefore based on the task new To provide compounds with herbicidal activity, the preferred have a higher effectiveness than the herbicidal substances of State of the art and / or better selectivity Have harmful plants.

It has now surprisingly been found that this task by the cyclohexenone derivatives of bicy clic benzoic acids, which in the 2,3-position have saturated heterocycle, is solved.

Accordingly, the present invention relates to cyclohexenone derivatives of bicyclic benzoic acids of the general formula I,

wherein
X represents O, S, SO, SO ₂ , NR ¹ or N-NR ¹ R ¹⁷ ,
R ^{1 is} hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ - Haloalkyl sulfonyl, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ haloalkylcarbonyl, C ₁ -C ₆ alkylcarbonyl-C ₁ -C ₆ alkyl , C ₁ -C ₆ -alkylcarbonyl-C ₁ -C ₆ -alkylcarbonyl, C ₁ -C ₆ -alkylcarbonyloxy-C ₁ -C ₆ -alkyl,
C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkoxy, C ₃ -C ₆ cycloalkylcarbonyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkoxy-C ₁ -C ₆ -alkyl, C ₃ -C ₆ -cycloalkylcarbonyl-C ₁ -C ₆ -alkyl, C ₃ -C ₆ -cycloalkoxycarbonyl-C ₁ -C ₆ -alkyl, C ₃ -C ₆ -cycloalkylcarbonyloxy-C ₁ - C ₆ alkyl, C ₃ -C ₆ cycloalkylsulfonyl,
Phenyl, phenylsulfonyl, phenylcarbonyl, phenyl-C ₁ -C ₆ -alkyl, phenyl-C ₁ -C ₆ -alkylcarbonyl, phenoxy-C ₁ -C ₆ -alkyl, phenylcarbonyl-C ₁ -C ₆ -alkyl, phenoxycarbonyl-C ₁ -C ₆ alkyl, or phenylcarbonyloxy-C ₁ -C ₆ alkyl,
Are heterocyclyl, heterocyclylsulfonyl, heterocyclylcarbonyl, heterocyclyl-C ₁ -C ₆ -alkyl, heterocyclylcarbonyl-C ₁ -C ₆ -alkyl or heterocyclylcarbonyloxy-C ₁ -C ₆ -alkyl,
where the phenyl, heterocyclyl and cycloalkyl radicals of the aforementioned groups optionally one, two, three or four substituents selected from C ₁ -C ₄ alkyl, C ₁ -C ₄ halo alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ -haloalkylcarbonyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ nalkylsulfonyl -Haloge, nitro, hydroxy or cyano wear and / or partially or can be fully halogenated;
R ² for halogen, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkyl sulfonyl or C ₁ -C ₆ -haloalkylsulfonyl;
R ^{3 represents} hydrogen, halogen, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl, and
Hex for substituted (3-oxo-1-cyclohexen-2-yl) carbonyl of the formula IIa or for substituted (1,3-dioxo-2-cyclohexyl) methylidene of the formula IIb

stand, whereby the variables R ⁴ to R ^{10 have the} following meaning:
R ⁴ hydroxy, mercapto, halogen, OR ¹¹ , SR ¹¹ , SOR ¹² , SO ₂ R ¹² , OSO ₂ R ¹² , P (O) R ¹³ R ¹⁴ , OP (O) R ¹³ R ¹⁴ , P (S) R ¹³ R ¹⁴ , OP (S) R ¹³ R ¹⁴ , NR ¹⁵ R ¹⁶ , ONR ¹⁵ R ¹⁶ or N-linked heterocyclyl, which can be partially or completely halogenated and / or can carry one, two or three of the following radicals: Nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy;
R ⁵ , R ⁹ independently of one another are hydrogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxycarbonyl;
R ⁶ , R ⁸ , R ¹⁰ independently of one another are hydrogen or C ₁ -C ₄ alkyl;
R ^{7 is} hydrogen, halogen, hydroxy, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, di- (C ₁ -C ₆ alkoxy) methyl, (C ₁ -C ₆ alkoxy) - (C ₁ -C ₆ alkylthio) methyl, di (C ₁ -C ₆ alkylthio) methyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ - C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ -Haloalkoxycarbonyl;
1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3 oxathian-2-yl, 1,3-dithiolan-2-yl or 1 , 3-dithian-2-yl, where the six latter radicals can be substituted by one to three C ₁ -C ₄ alkyl radicals; or
R ⁶ and R ⁸ or R ⁸ and R ¹⁰ together form an n bond or a C ₁ -C ₅ alkyl chain which can carry one or two residues from the following group: halogen, cyano, C ₁ -C ₄ - Alkyl, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ alkoxycarbonyl; or
R ⁶ and R ¹⁰ together form a C ₁ -C ₄ alkyl chain which can carry two or three radicals from the following group: halogen, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ alkoxycarbonyl; or
R ⁷ and R ⁸ together form an -O- (CH ₂ ) _p -O-, -O- (CH ₂ ) _p -S-, -S- (CH ₂ ) _p -S-, -O- (CH ₂ ) _q - or -S- (CH ₂ ) _q chain, in which p is 2, 3, 4 or 5 and q is 2, 3, 4, 5 or 6, and by one or two radicals from the following group may be substituted: halogen, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ alkoxycarbonyl; or
R ⁷ and R ⁸ together with the carbon to which they are bound form a carbonyl group; in which
and in which the variables R ¹¹ to R ^{17 have} the following meanings:
R ^{11 is} C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₆ haloalkynyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkylcarbonyl, C ₂ -C ₆ alkenylcarbonyl, C ₂ -C ₆ alkynylcarbonyl, C ₃ -C ₆ cycloalkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, C ₃ -C ₆ alkenyloxycarbonyl, C ₃ -C ₆ -alkynyloxycarbonyl, C ₁ -C ₆ -alkylthiocarbonyl, C ₁ -C ₆ -alkylaminocarbonyl, C ₃ -C ₆ -alkenylaminocarbonyl, C ₃ -C ₆ -alkynylaminocarbonyl, N, N-Di (C ₁ -C ₆ - alkyl) aminocarbonyl, N- (C ₃ -C ₆ alkenyl) -N- (C ₁ -C ₆ alkyl) aminocarbonyl, N- (C ₃ -C ₆ alkynyl) -N- (C ₁ -C ₆ -alkyl) -aminocarbonyl, N- (C ₁ -C ₆ -alkoxy) -N- (C ₁ -C ₆ -alkyl) -aminocarbonyl, N- (C ₃ -C ₆ -alkenyl) -N- (C ₁ - C ₆ -alkoxy) -aminocarbonyl, N- (C ₃ -C ₆ -alkynyl) -N- (C ₁ -C ₆ -alkoxy) -aminocarbonyl, di- (C ₁ -C ₆ -alkyl) -aminothiocarbonyl, C ₁ -C ₆ -alkoxyimino-C ₁ -C ₆ alkyl, where the alkyl, cycloalkyl or alkoxy radicals mentioned can be partially or completely halogenated and / or one, two or three of the fo Lying groups can carry: cyano, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, di- (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ - Alkoxycarbonyl, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkoxycarbonyl, hydroxycarbonyl, C ₁ -C ₄ alkylaminocarbonyl, di- (C ₁ -C ₄ alkyl) aminocarbonyl, aminocarbonyl, C ₁ -C ₄ alkylcarbonyloxy or C ₃ -C ₆ cycloalkyl;
Phenyl, phenyl-C ₁ -C ₆ -alkyl, phenylcarbonyl-C ₁ -C ₆ -alkyl, phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl, phenylaminocarbonyl, N- (C ₁ -C ₆ -alkyl) -N-phenylaminocarbonyl, phenyl-C ₂ -C ₆ -alkenylcarbonyl, heterocyclyl, heterocyclyl-C ₁ -C ₆ -alkyl, heterocyclylcarbonyl-C ₁ -C ₆ -alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylaminocarbonyl, N- (C ₁ -C ₆ -Al- heterocyclylaminocarbonyl or heterocyclyl-C ₁ -C ₆ -alkenylcarbonyl, where the phenyl or heterocyclyl radical of the 18 latter substituents can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C ₁ - C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy;
R ^{12 is} C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl or C ₃ -C ₆ cycloalkyl, where the four radicals mentioned can be partially or completely halogenated and / or one, can carry two or three of the following groups: cyano, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkylcarbonyl , C ₁ -C ₄ alkoxycarbonyl or C ₁ -C ₄ haloalkoxycarbonyl,
Phenyl, phenyl-C ₁ -C ₄ -alkyl, heterocyclyl or heterocyclyl-C ₁ -C ₄ -alkyl, where the phenyl or heterocyclyl radical of the four last-mentioned substituents can be partially or completely halogenated and / or one, two or can carry three of the following radicals: nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ alkoxycarbonyl ;
R ¹³ , R ¹⁴ independently of one another are hydrogen, hydroxy, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylthio, phenyl, phenyl-C ₁ -C ₄ -alkyl or phenoxy, where the three latter substituents can be partially or completely halogenated and / or can carry one, two or three of the following radicals: nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ - Alkoxy, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ alkoxy carbonyl;
R ^{15 is} hydrogen, C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₆ haloalkynyl, C ₃ -C ₆ - Cycloalkyl, C ₁ -C ₆ alkylcarbonyl, hydroxy, C ₁ -C ₆ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkynyloxy, amino, C ₁ -C ₆ alkylamino, di- (C ₁ -C ₆ alkyl) amino or C ₁ -C ₆ alkylcarbonylamino, where the alkyl, cycloalkyl or alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one, two or three of the following radicals: cyano, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkylaminocarbonyl, di- (C ₁ -C ₄ alkyl) aminocarbonyl or C ₃ -C ₆ cycloalkyl,
Phenyl, phenyl-C ₁ -C ₄ -alkyl, phenylcarbonyl, heterocyclyl, heterocycly-C ₁ -C ₄ -alkyl or heterocyclylcarbonyl, where the phenyl or heterocyclyl radical of the six last-mentioned substituents can be partially or completely halogenated and / or one can carry up to three of the following radicals: nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy;
R ¹⁶ , R ¹⁷ independently of one another are hydrogen, C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl;
and their agriculturally useful salts.

Herbicidal agents have also been found, the cyclohexenone deri vate of formula I contain and a very good herbicidal activity have. Processes for making these agents have also been developed and methods for controlling undesirable plant growth the cyclohexenone derivatives of the formula I found.

The compounds of formula I can, depending on the substitution pattern contain one or more chirality centers and are then located as Enantiomers or mixtures of diastereomers. Subject of he invention are both the pure enantiomers or diastereomers as well as their mixtures.

The compounds of formula I can also be in the form of their farmer useful salts are available, it depends on the type of Salt usually does not arrive. Generally they come Salts of those cations or the acid addition salts of those Acids into consideration, their cations, or anions, the herbicidal activity of the compounds I not adversely affected gene.  

The cations used are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and ammonium, with one to four hydrogen atoms by C ₁ if desired -C ₄ -alkyl, hydroxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, hydroxy-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, Phenyl or benzyl can be replaced, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2- (2-hydroxyeth-1-oxy) eth-1-ylammonium, di (2-hydroxyeth-1-yl) ammonium, trimethylbenzylammonium, des further phosphonium ions, sulfonium ions, preferably tri (C ₁ -C ₄ alkyl) sulfonium and sulfoxonium ions, preferably tri (C ₁ -C ₄ alkyl) sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C ₁ -C ₄ alkane acids, preferably formate, acetate Propionate and butyrate.

In the case of R ⁴ = hydroxy or mercapto {Y = O, S}, IIa also represents the tautomeric forms IIa ', IIa "and IIa'''

or IIb also representative of the tautomeric forms IIb ', IIb "and IIb'''

The organic molecule parts mentioned for the substituents R ¹ to R ¹⁶ or as residues on phenyl and heterocyclyl residues represent collective terms for individual lists of the individual group members. All hydrocarbon chains, that is to say all alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio -, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, N-alkylamino, N, N-dialkylamino, N-haloalkylamino, N-alkoxyamino, N-alkoxy-N-alkylamino, N- Alkylcarbonylamino-, alkylcarbonyl-, haloalkylcarbonyl-, alkoxycarbonyl-, haloalkoxycarbonyl-, alkylthiocarbonyl-, alkylcarbonyloxy-, alkylaminocarbonyl-, dialkylaminocarbonyl-, dialkylaminothiocarbonyl-, alkoxyalkyl-, alkoxyiminoalkyl-, phenylalkylcarbonyl-, heterocyl-phenyl-cyclo-alkylllyl-alkylphenylcyll-phenylcarbonyl-phenylcylphenyl Alkoxy-N-alkylaminocarbonyl, N-alkyl-N-phenylaminocarbonyl, N-alkyl-N-heterocyclylaminocarbonyl, phenylalkyl, heterocyclylalky l-, phenylcarbonylalkyl-, heterocyclylcarbonylalkyl-, alkoxyalkoxycarbonyl-, alkenylcarbonyl-, alkenyloxycarbonyl-, alkenylaminocarbonyl-, N-alkenyl-N-alkylaminocarbonyl-, N-alkenyl N-alkoxyaminocarbonyl-, alkynylcarbonyl, alkynylaminocarbonyl-, alkynyloxycarbonyl-, alkynyloxycarbonyl- -N-alkylaminocarbonyl, N-alkynyl, N-alkoxyaminocarbonyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkenyloxy, alkynyloxy, alkanediyl, alkenediyl, alkadienediyl or alkynediyl parts can be straight-chain or branched. Unless stated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms. Halogen is fluorine, chlorine, bromine or iodine.

Furthermore, for example:

• - C ₁ -C ₄ alkyl: e.g. B. methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;
• - C ₁ -C ₆ alkyl, and the alkyl parts of C ₁ -C ₆ alkylamino, di- (C ₁ -C ₆ alkyl) amino, N- (C ₁ -C ₆ alkoxy) -N- (C ₁ -C ₆ alkyl) amino, N (C ₁ -C ₆ alkoxy) -N- (C ₁ -C ₆ alkyl) aminocarbonyl, N- (C ₃ -C ₆ alkenyl) -N- (C ₁ -C ₆ -alkyl) -aminocarbonyl, (C ₃ -C ₆ -alkynyl) -N- (C ₁ -C ₆ -alkyl) -aminocarbonyl, N- (C ₁ -C ₆ -alkyl) -N-phenylaminocarbonyl, N- (C ₁ -C ₆ alkyl) -N-heterocyclylaminocarbonyl: C ₁ -C ₄ alkyl, as mentioned above, and z. B. 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-ethyl-1-methylpropyl or 1-ethyl-3 methylpropyl;
• - C ₁ -C ₄ haloalkyl: a C ₁ -C ₄ alkyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for. B. chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 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, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2- Difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2, 3,3,3-pentafluoropropyl, heptafluoropropyl, 1- (fluoromethyl) -2-fluoroethyl, 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2-bromethyl, 4-fluorobutyl, 4-chlorobutyl, 4- Bromobutyl or nonafluorobutyl;
• - C ₁ -C ₆ haloalkyl, and the haloalkyl parts of NC ₁ -C ₆ haloalkylamino: C ₁ -C ₄ haloalkyl, as mentioned above, and z. B. 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorhexyl, 6-chlorohexyl, 6-bromhexyl, 6-iodohexyl or dodecafluorhexyl;
• - C ₁ -C ₄ alkoxy: e.g. B. methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy;
• - C ₁ -C ₆ alkoxy, and the alkoxy parts of NC ₁ -C ₆ alkoxyamino, N- (C ₁ -C ₆ alkoxy) -N- (C ₁ -C ₆ alkyl) amino, C ₁ -C ₆ -alkoxyimino-C ₁ -C ₆ -alkyl, N- (C ₁ -C ₆ -alkoxy) -N- (C ₁ -C ₆ -alkyl) -aminocarbonyl, N- (C ₃ -C ₆ -alkenyl) - N- (C ₁ -C ₆ alkoxy) aminocarbonyl and N- (C ₃ -C ₆ alkynyl) -N- (C ₁ -C ₆ alkoxy) aminocarbonyl: C ₁ -C ₄ alkoxy as above called, and z. B. pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3- Methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;
• - C ₁ -C ₄ haloalkoxy: a C ₁ -C ₄ alkoxy radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for. B. fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2 fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2 -Chlor-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3 -Bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy , 1- (fluoromethyl) -2-fluoroethoxy, 1- (chloromethyl) -2-chloroethoxy, 1- (bromomethyl) -2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy;
• - C ₁ -C ₆ haloalkoxy: C ₁ -C ₄ haloalkoxy, as mentioned above, and z. B. 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorhexoxy;
• - C ₁ -C ₄ alkylthio (C ₁ -C ₄ alkylsulfanyl: C ₁ -C ₄ alkyl-S-): e.g. B. methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or 1,1-dimethylethylthio;
• - C ₁ -C ₆ -Alkylthio, and the alkylthio parts of C ₁ -C ₆ -alkylthiocarbonyl: C ₁ -C ₄ -alkylthio, as mentioned above, and z. B. pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 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 or 1-ethyl-2-methylpropylthio;
• - C ₁ -C ₄ haloalkylthio: a C ₁ -C ₄ alkylthio radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is to say, for. B. fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloro 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-tri-chloropropylthio, 2,2,3,3,3- Pentafluoropropylthio, heptafluoropropylthio, 1- (fluoromethyl) -2-fluoroethylthio, 1- (chloromethyl) -2-chloroethylthio, 1- (bromomethyl) -2-bromethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio;
• C ₁ -C ₆ haloalkylthio: C ₁ -C ₄ haloalkylthio, as mentioned above, and 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorhexylthio, 6-chlorohexylthio, 6- Bromhexylthio, 6-iodohexylthio or dodecafluorohexylthio;
• - C ₁ -C ₄ alkylsulfinyl (C ₁ -C ₄ alkyl-S (= O) -): e.g. B. methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl or 1,1-dimethylethylsulfinyl;
• C ₁ -C ₆ alkylsulfinyl: C ₁ -C ₄ alkylsulfinyl, as mentioned above, and pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1- Dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-sulfyl 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2 methylpropylsulfinyl ;
• - C ₁ -C ₄ haloalkylsulfinyl: C ₁ -C ₄ alkylsulfinyl, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for. B. fluoromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl, 2,2,2-trifluoromethyl, 2,2,2-trifluoromethyl 2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2-bromopropylsulfinyl, 2-bromopropylsulfinyl 3-bromopropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl, 2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl, 2,2,3,3,3-pentafluoropropylsulfinyl, Heptafluoropropylsulfinyl, 1- (fluoromethyl) -2-fluoroethylsulfinyl, 1- (chloromethyl) -2-chloroethylsulfinyl, 1- (bromomethyl) -2-bromomethylsulfinyl, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl or nonafluorobutylsulfinyl;
• - C ₁ -C ₆ haloalkylsulfinyl: C ₁ -C ₄ haloalkylsulfinyl, as mentioned above, and 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-bromopentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorhexylsulfinyl, 6-chlorohexylsulfinyl Bromhexylsulfinyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl;
• - C ₁ -C ₄ alkylsulfonyl (C ₁ -C ₄ alkyl-S (= O) ₂ -) z. B. methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl or 1,1-dimethylethylsulfonyl;
• - C ₁ -C ₆ alkylsulfonyl: C ₁ -C ₄ alkylsulfonyl, as mentioned above, and pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2, 2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylsulfonyl, 1,3-dimethylsulfonyl, 1,3-dimethylsulfonyl 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2- methylpropylsulfonyl;
• - C ₁ -C ₄ haloalkylsulfonyl is a C ₁ -C ₄ alkylsulfonyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for. B. fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoromethylsulfonylsulfonylsulfonyl, 2,2-difluoromethylsulfonylsulfonyl, 2,2-difluoromethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonylsulfonyl, 2-chloropropylsulfonyl 3-bromopropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl, Heptafluoropropylsulfonyl, 1- (fluoromethyl) -2-fluoroethylsulfonyl, 1- (chloromethyl) -2-chloroethylsulfonyl, 1- (bromomethyl) -2-bromomethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutyl;
• - C ₁ -C ₆ haloalkysulfonyl: C ₁ -C ₄ haloalkylsulfonyl, as mentioned above, and 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl, 5-iodopentylsulfonyl, 6-fluorhexylsulfonyl, 6-bromhexylsulfonyl or 6-bromophenylsulfonyl Dodecafluorohexylsulfonyl;
• C ₁ -C ₆ alkylamino: methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1,1-dimethylethylamino, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2 , 2-dimethylpropylamino, 1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino , 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1 -Ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino;
• - Di- (C ₁ -C ₄ alkyl) amino, i.e. z. B. N, N-dimethylamino, N, N-diethylamino, N, N-dipropylamino, N, N-di- (1-methylethyl) amino, N, N-dibutylamino, N, N-di- (1-methylpropyl) amino, N, N-di- (2-methylpropyl) amino, N, N-di- (1,1-dimethylethyl) amino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl- N- (1-methylethyl) amino, N-butyl-N-methylamino, N-methyl-N- (1-methylpropyl) amino, N-methyl-N- (2-methylpropyl) amino, N- (1,1- Dimethylethyl) -N-methylamino, N-ethyl-N-propylamino, N-ethyl-N- (1-methylethyl) amino, N-butyl-N-ethylamino, N-ethyl-N- (1-methylpropyl) amino, N -Ethyl-N- (2-methylpropyl) amino, N-ethyl-N- (1,1-dimethylethyl) amino, N- (1-methylethyl) -N-propylamino, N-butyl-N-propylamino, N- ( 1-methylpropyl) -N-propylamino, N- (2-methylpropyl) -N-propylamino, N- (1,1-dimethylethyl) -N-propylamino, N-butyl-N- (1-methylethyl) amino, N- (1-methylethyl) -N- (1-methylpropyl) amino, N- (1-methylethyl) -N- (2-methylpropyl) amino, N- (1,1-dimethylethyl) -N- (1-methylethyl) amino , N-butyl-N- (1-methylpropyl) amino, N-butyl-N- (2-methylpropyl) amino, N-butyl-N- (1,1-dimethy ethyl) amino, N- (1-methylpropyl) -N- (2-methylpropyl) amino, N- (1,1-dimethylethyl) -N- (1-methylpropyl) amino or N- (1,1-dimethylethyl ) -N- (2-methylpropyl) amino;
• - Di- (C ₁ -C ₆ -alkyl) amino: di- (C ₁ -C ₄ -alkyl) amino as mentioned above, and N, N-dipentylamino, N, N-dihexylamino, N-methyl-N-pentylamino , N-ethyl-N-pentylamino, N-methyl-N-hexylamino or N-ethyl-N-hexylamino;
• - C ₁ -C ₄ alkylcarbonyl: e.g. B. methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or 1,1-dimethylethylcarbonyl;
• - C ₁ -C ₆ -alkylcarbonyl, and the alkylcarbonyl radicals of C ₁ -C ₆ -alkylcarbonyl-C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkylcarbonylamino: C ₁ -C ₄ -alkylcarbonyl, as mentioned above, and e.g. B. pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3- Methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2, -dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl , 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl;
• - C ₁ -C ₄ haloalkylcarbonyl: a C ₁ -C ₄ alkylcarbonyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for. B. chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl, difluoroacetyl, trifluoroacetyl, chlorofluoroacetyl, dichloro-fluoroacetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethyl-2,2-carbonyl-2,2-carbonyl Trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, pentafluoroethylcarbonyl, 2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2, 2-difluoropropylcarbonyl, 2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl, 3,3,3-trichloropropylcarbonyl, 2, 2,3,3,3-pentafluoropropylcarbonyl, heptafluoropropylcarbonyl, 1- (fluoromethyl) -2-fluoroethylcarbonyl, 1- (chloromethyl) -2-chloroethylcarbonyl, 1- (bromomethyl) -2-bromethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl or nonafluorobutylcarbonyl;
• C ₁ -C ₆ haloalkylcarbonyl: a C ₁ -C ₄ haloalkylcarbonyl radical as mentioned above, and 5-fluoropentylcarbonyl, 5-chloropentylcarbonyl, 5-bromopentylcarbonyl, perfluoropentylcarbonyl, 6-fluorhexylcarbonyl, 6-chlorohexylcarbonyl, 6-bromohexylcarbonyl or perfluorhexylcarbonyl;
• - C ₁ -C ₄ alkoxycarbonyl so z. B. methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1,1-dimethylethoxycarbonyl;
• - C ₁ -C ₆ alkoxycarbonyl: C ₁ -C ₄ alkoxycarbonyl, as mentioned above, and z. B. pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3- Methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methyl-propoxycarbonyl or 1-ethyl-2-methyl-propoxycarbonyl;
• - C ₁ -C ₄ haloalkoxycarbonyl: a C ₁ -C ₄ alkoxycarbonyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for. B. fluoromethoxycarbonyl, difluoromethoxycarbonyl, trifluoromethoxycarbonyl, chlorodifluoromethoxycarbonyl, bromodifluoromethoxycarbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2,2-difluoroethoxycarbonyl, 2,2,2-trifluorocarbonyl, 2,2,2-trifluoromethoxycarbonyl 2-chloro-2,2-difluoroethoxycarbonyl, 2,2-dichloro-2-fluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, pentafluoroethoxycarbonyl, 2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl, 2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl, 2,2-difluoropropoxycarbonyl, 2,3-difluoropropoxycarbonyl, 2,3-dichloropropoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl, 3,3,3-trichloropropoxycarbonyl, 2,2,3,3,3-pentafluoropropoxycarbonyl, Heptafluoropropoxycarbonyl, 1- (fluoromethyl) -2-fluoroethoxycarbonyl, 1- (chloromethyl) -2-chloroethoxycarbonyl, 1- (bromomethyl) -2-bromethoxycarbonyl, 4-fluorobutoxycarbonyl, 4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl or 4-iodobutoxycarbonyl;
• - C ₁ -C ₆ halooxycarbonyl: a C ₁ -C ₄ halooxycarbonyl radical as mentioned above, and 5-fluoropentoxycarbonyl, 5-chloropentoxycarbonyl, 5-bromopentoxycarbonyl, 6-fluorohexoxycarbonyl, 6-chlorohexoxycarbonyl or 6-bromohexoxycarbonyl;
• - (C ₁ -C ₄ alkyl) carbonyloxy: acetyloxy, ethylcarbonyloxy, propylcarbonyloxy, 1-methylethylcarbonyloxy, butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy or 1,1-dimethylethylcarbonyloxy;
• - (C ₁ -C ₄ alkylamino) carbonyl: e.g. B. methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl, butylaminocarbonyl, 1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or 1,1-dimethylethylaminocarbonyl;
• - (C ₁ -C ₆ alkylamino) carbonyl: (C ₁ -C ₄ alkylamino) carbonyl, as mentioned above, and z. B. pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylylpentocaminylcarbonyl, 1-methylbutylaminocarbonyl, 1 Methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl, 1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl, 3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminyl-2-ethylbutylaminyl 1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl, 1-ethyl-1-methylpropylaminocarbonyl or 1-ethyl -2-methylpropylaminocarbonyl;
• - Di- (C ₁ -C ₄ alkyl) aminocarbonyl: e.g. B. N, N-dimethylaminocarbonyl, N, N-diethylaminocarbonyl, N, N-di- (1-methylethyl) aminocarbonyl, N, N-dipropylaminocarbonyl, N, N-dibutylaminocarbonyl, N, N-di- (1-methylpropyl) -aminocarbonyl, N, N-di- (2-methylpropyl) -aminocarbonyl, N, N-di- (1,1-dimethylethyl) -aminocarbonyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N -Methyl-N- (1-methylethyl) aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N- (1-methylpropyl) aminocarbonyl, N-methyl-N- (2-methylpropyl) aminocarbonyl, N - (1,1-Dimethylethyl) -N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl-N- (1-methylethyl) aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-N- ( 1-methylpropyl) aminocarbonyl, N-ethyl-N- (2-methylpropyl) aminocarbonyl, N-ethyl-N- (1,1-dimethylethyl) aminocarbonyl, N- (1-methylethyl) -N-propylaminocarbonyl, N -Butyl-N-propylaminocarbonyl, N- (1-methylpropyl) -N-propylaminocarbonyl, N- (2-methylpropyl) -N-propylaminocarbonyl, N- (1,1-dimethylethyl) -N-propylaminocarbonyl, N-butyl-N - (1-methylethyl) aminocarb onyl, N- (1-methylethyl) -N- (1-methylpropyl) aminocarbonyl, N- (1-methylethyl) -N- (2-methylpropyl) aminocarbonyl, N- (1,1-dimethylethyl) -N- (1-methylethyl) aminocarbonyl, N-butyl-N- (1-methylpropyl) aminocarbonyl, N-butyl-N- (2-methylpropyl) aminocarbonyl, N-butyl-N- (1,1-dimethylethyl) - aminocarbonyl, N- (1-methylpropyl) -N- (2-methylpropyl) aminocarbonyl, N- (1,1-dimethylethyl) -N- (1-methylpropyl) aminocarbonyl or N- (1,1-dimethylethyl) - N- (2-methylpropyl) aminocarbonyl;
• - Di- (C ₁ -C ₆ -alkyl) -aminocarbonyl: Di- (C ₁ -C ₄ -alkyl) -aminocarbonyl, as mentioned above, and z. B. N-methyl-N-pentylaminocarbonyl, N-methyl-N- (1-methylbutyl) aminocarbonyl, N-methyl-N- (2-methylbutyl) aminocarbonyl, N-methyl-N- (3-methylbutyl) - aminocarbonyl, N-methyl-N- (2,2-dimethylpropyl) aminocarbonyl, N-methyl N- (1-ethylpropyl) aminocarbonyl, N-methyl-N-hexylaminocarbonyl, N-methyl N- (1,1-dimethylpropyl ) -aminocarbonyl, N-methyl-N- (1,2-dimethylpropyl) -aminocarbonyl, N-methyl-N- (1-methylpentyl) -aminocarbonyl, N-methyl-N- (2-methylpentyl) -aminocarbonyl, N- Methyl-N- (3-methylpentyl) aminocarbonyl, N-methyl-N- (4-methylpentyl) aminocarbonyl, N-methyl-N- (1,1-dimethylbutyl) aminocarbonyl, N-methyl-N- (1 , 2-dimethylbutyl) aminocarbonyl, N-methyl-N- (1,3-dimethylbutyl) aminocarbonyl, N-methyl-N- (2,2-dimethylbutyl) aminocarbonyl, N-methyl N- (2,3- dimethylbutyl) aminocarbonyl, N-methyl-N- (3,3-dimethylbutyl) aminocarbonyl, N-methyl N- (1-ethylbutyl) aminocarbonyl, N-methyl-N- (2-ethylbutyl) aminocarbonyl, N- Methyl N- (1,1,2-trimethylpropylj-aminocarbonyl, N-methyl-N- (1,2,2-trimethylpropyl) aminocarbo nyl, N-methyl-N- (1-ethyl-1-methylpropyl) aminocarbonyl, N-methyl-N- (1-ethyl-2-methylpropyl) aminocarbonyl, N-ethyl-N-pentylaminocarbonyl, N-ethyl N - (1-methylbutyl) aminocarbonyl, N-ethyl-N- (2-methylbutyl) aminocarbonyl, N-ethyl-N- (3-methylbutyl) aminocarbonyl, N-ethyl-N- (2,2-dimethylpropyl) -aminocarbonyl, N-ethyl-N- (1-ethylpropyl) aminocarbonyl, N-ethyl-N-hexylaminocarbonyl, N-ethyl N- (1,1-dimethylpropyl) aminocarbonyl, N-ethyl-N- (1,2 -dimethylpropyl) -aminocarbonyl, N-ethyl-N- (1-methylpentyl) -aminocarbonyl, N-ethyl-N- (2-methylpentyl) -aminocarbonyl, N-ethyl-N- (3-methylpentyl) -aminocarbonyl, N- Ethyl-N- (4-methylpentyl) aminocarbonyl, N-ethyl N- (1,1-dimethylbutyl) aminocarbonyl, N-ethyl-N- (1,2-dimethylbutyl) aminocarbonyl, N-ethyl-N- ( 1,3-dimethylbutyl) aminocarbonyl, N-ethyl-N- (2,2-dimethylbutyl) aminocarbonyl, N-ethyl-N- (2,3-dimethylbutyl) aminocarbonyl, N-ethyl-N- (3, 3-dimethylbutyl) aminocarbonyl, N-ethyl-N- (1-ethylbutyl) aminocarbonyl, N-ethyl-N- (2-ethylbutyl) aminocarbonyl, N-ethyl-N- (1 , 1,2-trimethylpropyl) aminocarbonyl, N-ethyl-N- (1,2,2-trimethylpropyl) aminocarbonyl, N-ethyl-N- (1-ethyl-1-methylpropyl) aminocarbonyl, N-ethyl- N- (1-ethyl-2-methylpropyl) aminocarbonyl, N-propyl-N-pentylaminocarbonyl, N-butyl-N-pentylaminocarbonyl, N, N-dipentylaminocarbonyl, N-propyl-N-hexylaminocarbonyl, N-butyl-N- hexylaminocarbonyl, N-pentyl, N-hexylaminocarbonyl or N, N-dihexylaminocarbonyl;
• - Di (C ₁ -C ₆ alkyl) aminothiocarbonyl: e.g. B. N, N-Dimethylaminothiocarbonyl, N, N-Diethylaminothiocarbonyl, N, N-Di- (1-methylethyl) aminothiocarbonyl, N, N-Dipropylaminothiocarbonyl, N, N-Dibutylaminothiocarbonyl, N, N-Di- (1-methylpropyl) -aminothiocarbonyl, N, N-di- (2-methylpropyl) -aminothiocarbonyl, N, N-di- (1,1-dimethylethyl) -aminothiocarbonyl, N-ethyl-N-methylaminothiocarbonyl, N-methyl-N-propylaminothiocarbonyl, N -Methyl-N- (1-methylethyl) aminothiocarbonyl, N-butyl-N-methylaminothiocarbonyl, N-methyl-N- (1-methylpropyl) aminothiocarbonyl, N-methyl-N- (2-methylpropyl) aminothiocarbonyl, N - (1,1-Dimethylethyl) -N-methylaminothiocarbonyl, N-ethyl-N-propylaminothiocarbonyl, N-ethyl-N- (1-methylethyl) -aminothiocarbonyl, N-butyl-N-ethylaminothiocarbonyl, N-ethyl-N- ( 1-methylpropyl) aminothiocarbonyl, N-ethyl-N- (2-methylpropyl) aminothiocarbonyl, N-ethyl-N- (1,1-dimethylethyl) aminothiocarbonyl, N- (1-methylethyl) -N-propylaminothiocarbonyl, N -Butyl-N-propylaminothiocarbonyl, N- (1-methylpropyl) -N-propylaminothiocarbonyl, N- (2-methylpropyl) -N-propy laminothiocarbonyl, N- (1,1-dimethylethyl) -N-propylaminothiocarbonyl, N-butyl-N- (1-methylethyl) -aminothiocarbonyl, N- (1-methylethyl) -N- (1-methylpropyl) -aminothiocarbonyl, N- (1-methylethyl) -N- (2-methylpropyl) aminothiocarbonyl, N- (1,1-dimethylethyl) -N- (1-methylethyl) aminothiocarbonyl, N-butyl-N- (1-methylpropyl) aminothiocarbonyl, N-butyl N- (2-methylpropyl) aminothiocarbonyl, N-butyl-N- (1,1-dimethylethyl) aminothiocarbonyl, N- (1-methylpropyl) -N- (2-methylpropyl) aminothiocarbonyl, N- ( 1,1-dimethylethyl) -N- (1-methylpropyl) aminothiocarbonyl, N- (1,1-dimethylethyl) -N- (2-methylpropyl) aminothiocarbonyl, N-methyl-N-pentylaminothiocarbonyl, N-methyl-N - (1-methylbutyl) aminothiocarbonyl, N-methyl-N- (2-methylbutyl) aminothiocarbonyl, N-methyl-N- (3-methylbutyl) aminothiocarbonyl, N-methyl-N- (2,2-dimethylpropyl) -aminothiocarbonyl, N-methyl N- (1-ethylpropyl) -aminothiocarbonyl, N-methyl-N-hexylaminothiocarbonyl, N-methyl-N- (1,1-dimethylpropyl) -aminothiocarbonyl, N-methyl N- (1,2- dimethylpropyl) aminothi ocarbonyl, N-methyl-N- (1-methylpentyl) aminothiocarbonyl, N-methyl-N- (2-methylpentyl) aminothiocarbonyl, N-methyl N- (3-methylpentyl) aminothiocarbonyl, N-methyl-N- ( 4-methylpentyl) aminothiocarbonyl, N-methyl-N- (1,1-dimethylbutyl) aminothiocarbonyl, N-methyl-N- (1,2-dimethylbutyl) aminothiocarbonyl, N-methyl-N- (1,3- dimethylbutyl) aminothiocarbonyl, N-methyl-N- (2,2-dimethylbutyl) aminothiocarbonyl, N-methyl-N- (2,3-dimethylbutyl) aminothiocarbonyl, N-methyl-N- (3,3-dimethylbutyl) -aminothiocarbonyl, N-methyl-N- (1-ethylbutyl) -aminothiocarbonyl, N-methyl-N- (2-ethylbutyl) -aminothiocarbonyl, N-methyl-N-ethyl-N- (1,1,2-trimethylpropyl) -aminothiocarbonyl, N-methyl-N- (1,2,2-trimethylpropyl) -aminothiocarbonyl, N-methyl-N- (1-ethyl-1-methylpropyl) -aminothiocarbonyl, N-methyl-N- (1-ethyl- 2-methylpropyl) aminothiocarbonyl, N-ethyl-N-pentylaminothiocarbonyl, N-ethyl-N- (1-methylbutyl) aminothiocarbonyl, N-ethyl-N- (2-methylbutyl) aminothiocarbonyl, N-ethyl-N- ( 3-methylbutyl) aminothiocarbonyl, N-ethyl-N- (2,2- dimethylpropyl) aminothiocarbonyl, N-ethyl-N- (1-ethylpropyl) aminothiocarbonyl, N-ethyl-N-hexylaminothiocarbonyl, N-ethyl-N- (1,1-dimethylpropyl) aminothiocarbonyl, N-ethyl-N- ( 1,2-dimethylpropyl) aminothiocarbonyl, N-ethyl-N- (1-methylpentyl) aminothiocarbonyl, N-ethyl-N- (2-methylpentyl) aminvthiocarbonyl, N-ethyl-N- (3-methylpentyl) aminothiocarbonyl , N-ethyl-N- (4-methylpentyl) aminothiocarbonyl, N-ethyl-N- (1,1-dimethylbutyl) aminothiocarbonyl, N-ethyl-N- (1,2-dimethylbutyl) aminothiocarbonyl, N-ethyl -N- (1,3-dimethylbutyl) aminothiocarbonyl, N-ethyl-N- (2,2-dimethylbutyl) aminothiocarbonyl, N-ethyl-N- (2,3-dimethylbutyl) aminothiocarbonyl, N-ethyl-N - (3,3-dimethylbutyl) aminothiocarbonyl, N-ethyl-N- (1-ethylbutyl) aminothiocarbonyl, N-ethyl-N- (2-ethylbutyl) aminothiocarbonyl, N-ethyl-N- (1,1, 2-trimethylpropyl) aminothiocarbonyl, N-ethyl-N- (1,2,2-trimethylpropyl) aminothiocarbonyl, N-ethyl-N- (1-ethyl-1-methylpropyl) aminothiocarbonyl, N-ethyl N- (1 -ethyl-2-methylpropyl) aminothiocarbonyl, N-prop yl-N-pentylaminothiocarbonyl, N-butyl-N-pentylaminothiocarbonyl, N, N-dipentylaminothiocarbonyl, N-propyl-N-hexylaminothiocarbonyl, N-butyl-N-hexylaminothiocarbonyl, N-pentyl-N-hexylaminothiocarbonyl or N,
• - C ₁ -C ₆ hydroxyalkyl: C ₁ -C ₆ alkyl substituted by one to three OH groups, e.g. B. hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1,2-bishydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 4-hydroxybutyl, 2,2-dimethyl-3-hydroxy propyl;
• - Phenyl-C ₁ -C ₆ -alkyl: C ₁ -C ₆ -alkyl substituted by a phenyl radical, e.g. B. benzyl, 1-phenylethyl and 2-phenylethyl, where the phenyl radical may be partially or completely halogenated in the manner indicated or may have one to three of the substituents indicated above for phenyl; Heterocyclyl-C ₁ -C ₆ -alkyl accordingly represents a C ₁ -C ₆ -alkyl substituted by a heterocyclyl radical;
• - C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkyl: C ₁ -C ₆ alkoxy, as mentioned above, substituted C ₁ -C ₆ alkyl, that is, for. B. methoxymethyl, ethoxymethyl, propoxymethyl, (1-methylethoxy) methyl, butoxymethyl, (1-methylpropoxy) methyl, (2-methylpropoxy) methyl, (1,1-dimethylethoxy) methyl, 2- (methoxy) ethyl, 2- (Ethoxy) ethyl, 2- (propoxy) ethyl, 2- (1-methylethoxy) ethyl, 2- (butoxy) ethyl, 2- (1-methylpropoxy) ethyl, 2- (2-methylpropoxy) ethyl, 2- (1 , 1-Dimethylethoxy) ethyl, 2- (methoxy) propyl, 2- (ethoxy) propyl, 2- (propoxy) propyl, 2- (1-methylethoxy) propyl, 2- (butoxy) propyl, 2- (1 -Methylpropoxy) propyl, 2- (2-methylpropoxy) propyl, 2- (1,1-dimethylethoxy) propyl, 3- (methoxy) propyl, 3- (ethoxy) propyl, 3- (propoxy) propyl, 3- ( 1-methylethoxy) propyl, 3- (butoxy) propyl, 3- (1-methylpropoxy) propyl, 3- (2-methylpropoxy) propyl, 3- (1,1-dimethylethoxy) propyl, 2- (methoxy) butyl, 2 - (Ethoxy) butyl, 2- (propoxy) butyl, 2- (1-methylethoxy) butyl, 2- (butoxy) butyl, 2- (1-methylpropoxy) butyl, 2- (2-methylpropoxy) butyl, 2- ( 1,1-dimethylethoxy) butyl, 3- (methoxy) butyl, 3- (ethoxy) butyl, 3- (propoxy) butyl, 3- (1-methylethoxy) butyl, 3- (butoxy) butyl, 3- (1 -Methylpropox y) butyl, 3- (2-methylpropoxy) butyl, 3- (1,1-dimethylethoxy) butyl, 4- (methoxy) butyl, 4- (ethoxy) butyl, 4- (propoxy) butyl, 4- (1 -Methylethoxy) butyl, 4- (butoxy) butyl, 4- (1-methylpropoxy) butyl, 4- (2-methylpropoxy) butyl or 4- (1,1-dimethylethoxy) butyl;
• C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkoxy, and the alkoxyalkoxy parts of C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkoxycarbonyl: by C ₁ -C ₆ alkoxy, as mentioned above, substituted C ₁ -C ₆ alkoxy, e.g. B. for methoxymethoxy, ethoxymethoxy, propoxymethoxy, (1-methylethoxy) methoxy, butoxymethoxy, (1-methylpropoxy) methoxy, (2-methylpropoxy) methoxy, (1,1-dimethylethoxy) methoxy, 2- (methoxy) ethoxy, 2- (Ethoxy) ethoxy, 2- (propoxy) ethoxy, 2- (1-methylethoxy) ethoxy, 2- (butoxy) ethoxy, 2- (1-methylpropoxy) ethoxy, 2- (2-methylpropoxy) ethoxy, 2- (1 , 1-Dimethylethoxy) ethoxy, 2- (methoxy) propoxy, 2- (ethoxy) propoxy, 2- (propoxy) propoxy, 2- (1-methylethoxy) propoxy, 2- (butoxy) propoxy, 2- (1- Methylpropoxy) propoxy, 2- (2-methylpropoxy) propoxy, 2- (1,1-dimethylethoxy) propoxy, 3- (methoxy) propoxy, 3- (ethoxy) propoxy, 3- (propoxy) propoxy, 3- (1 -Methylethoxy) propoxy, 3- (butoxy) propoxy, 3- (1-methylpropoxy) propoxy, 3- (2-methylpropoxy) propoxy, 3- (1,1-dimethylethoxy) propoxy, 2- (methoxy) butoxy, 2 - (Ethoxy) butoxy, 2- (propoxy) butoxy, 2- (1-methylethoxy) butoxy, 2- (butoxy) butoxy, 2- (1-methylpropoxy) butoxy, 2- (2-methylpropoxy) butoxy, 2- (1,1-dimethylethoxy) butoxy, 3- (methoxy) butoxy, 3- (ethoxy) butoxy, 3- (propoxy) butoxy, 3- (1-methyl ethoxy) butoxy, 3- (butoxy) butoxy, 3- (1-methylpropoxy) butoxy, 3- (2-methylpropoxy) butoxy, 3- (1,1-dimethylethoxy) butoxy, 4- (methoxy) butoxy, 4- (Ethoxy) butoxy, 4- (propoxy) butoxy, 4- (1-methylethoxy) butoxy, 4- (butoxy) butoxy, 4- (1-methylpropoxy) butoxy, 4- (2-methylpropoxy) butoxy or 4- (1 , 1-dimethylethoxy) butoxy;
• C ₁ -C ₆ alkylcarbonyl-C ₁ -C ₆ alkyl: C ₁ -C ₆ alkyl substituted by a C ₁ -C ₆ alkylcarbonyl group, in which both of the C ₁ -C ₆ alkyl groups have one or more substituents, selected from C ₁ -C ₄ alkoxy and / or hydroxy: z. B. acetylmethyl (= 2-oxopropyl), 2- (acetyl) ethyl (= 3-oxo-n-butyl), 3-oxo-n-pentyl, 1,1-dimethyl-2-oxopropyl, 3-hydroxy-2 -oxopropyl or 3-hydroxy-2-oxobutyl;
• - C ₃ -C ₆ alkenyl, and the alkenyl parts of C ₃ -C ₆ alkenylcarbonyl, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkenyloxycarbonyl, C ₃ -C ₆ alkenylaminocarbonyl, N- (C ₃ -C ₆ -alkenyl) -N- (C ₁ -C ₆ ) alkylaminocarbonyl, N- (C ₃ -C ₆ -alkenyl) -N- (C ₁ -C ₆ -alkoxy) aminocarbonyl: e.g. B. prop-2-en-1-yl, but-1-en-4-yl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, 2-buten-1-yl, 1-penten-3-yl, 1-penten-4-yl, 2-penten-4-yl, 1-methyl-but-2-en-1-yl, 2-methyl but-2-en-1-yl, 3-methyl-but-2-en-1-yl, 1-methyl-but-3-en-1-yl, 2 methyl-but-3-en-1-yl , 3-methyl-but-3-en-1-yl, 1,1-dimethyl-prop-2-en-1-yl, 1,2-dimethyl-prop-2-en-1-yl, 1-ethyl prop-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl, 1-methylpent-3-ene -1-yl, 2-methyl-pent-3-en-1-yl, 3-methyl-pent-3-en-1-yl, 4-methyl-pent-3-en-1-yl, 1-methyl pent-4-en-1-yl, 2-methyl-pent-4-en-1-yl, 3-methyl-pent-4-en-1-yl, 4-methyl-pent-4-en-1 -yl, 1,1-dimethyl-but-2-en-1-yl, 1,1-dimethyl-but-3-en-1-yl, 1,2-dimethyl-but-2-en-1-yl , 1,2-dimethyl-but-3-en-1-yl, 1,3-dimethyl-but-2-en-1-yl, 1,3-dimethyl-but-3-en-1-yl, 2nd , 2-Dimethyl-but-3-en-1-yl, 2,3-dimethyl-but-2-en-1-yl, 2,3-dimethyl-but-3-en-1-yl, 3,3 -Dimethylbut-2-en-1-yl, 1-ethyl-but-2-en-1-yl, 1-ethyl-but-3-en-1-yl, 2-ethyl-but-2-en- 1-yl, 2-ethyl-but-3-en-1-yl, 1,1,2-trimethy l-prop-2-en-1-yl, 1-ethyl-1-methyl-prop-2-en-1-yl or 1-ethyl-2-methyl-prop-2-en-1-yl;
• - C ₂ -C ₆ alkenyl, and the alkenyl parts of C ₂ -C ₆ alkenylcarbonyl, phenyl-C ₂ -C ₆ alkenylcarbonyl and heterocyclyl-C ₂ -C ₆ alkenylcarbonyl: C ₃ -C ₆ alkenyl, such as mentioned above, and ethenyl;
• - C ₃ -C ₆ haloalkenyl: a C ₃ -C ₆ alkenyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for. B. 2-chloroallyl, 3-chloroallyl, 2,3-dichlorallyl, 3,3-dichloroallyl, 2,3,3-tri-chloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl;
• - C ₃ -C ₆ alkynyl, and the alkynyl parts of C ₃ -C ₆ alkynylcarbonyl, C ₃ -C ₆ alkynyloxy, C ₃ -C ₆ alkynyloxycarbonyl, C ₃ -C ₆ alkynylaminocarbonyl, N- (C ₃ -C ₆ -alkynyl) -N- (C ₁ -C ₆ -alkyl) -aminocarbonyl, N- (C ₃ -C ₆ -alkynyl) N- (C ₁ -C ₆ -alkoxyaminocarbonyl: e.g. propargyl, but -1-in-3-yl, but-1-in-4-yl, but-2-in-1-yl, pent-1-in-3-yl, pent-1-in-4-yl, pent -1-in-5-yl, pent-2-in-1-yl, pent-2-in-4-yl, pent-2-in-5-yl, 3-methyl-but-1-in-3 -yl, 3 methyl-but-1-in-4-yl, hex-1-in-3-yl, hex-1-in-4-yl, hex-1-in-5-yl, hex-1- in-6-yl, hex-2-in-1-yl, hex-2-in-4-yl, hex-2-in-5-yl, hex-2-in-6-yl, hex-3- in-1-yl, hex-3-in-2-yl, 3-methyl-pent-1-in-3-yl, 3-methyl-pent-1-in-4-yl, 3-methyl-pent 1-in-5-yl, 4-methyl-pent-2-in-4-yl or 4-methyl-pent-2-in-5-yl;
• - C ₂ -C ₆ alkynyl, and the alkynyl parts of C ₂ -C ₆ alkynylcarbonyl: C ₃ -C ₆ alkynyl, as mentioned above, and ethynyl;
• - C ₃ -C ₆ haloalkynyl: a C ₃ -C ₆ alkynyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for. B. 1,1-difluoroprop-2-in-1-yl, 3-iodo-prop-2-in-1-yl, 4-fluorobut-2-in-1-yl, 4-chlorobut-2- in-1-yl, 1,1-difluorobut-2-in-1-yl, 4-iodo-but-3-in-1-yl, 5-fluoropent-3-in-1-yl, 5-iodine pent-4-in-1-yl, 6-fluoro-hex-4-in-1-yl or 6-iodo-hex-5-in-1-yl;
• - C ₁ -C ₆ alkanediyl: methanediyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl , Propane-2,2-diyl, butane-1,1-diyl, butane-1,2-diyl, butane-1,3-diyl, butane-1,4-diyl, 2-methyl-propane-1,3 -diyl, 2-methyl-propane-1,2-diyl, 2-methyl-propane-1,1-diyl, 1-methyl-propane-1,2-diyl, 1-methyl-propane-2,2-diyl , 1-methyl-propane-1,1-diyl, pentane-1,1-diyl, pentane-1,2-diyl, pentane-1,3-diyl, pentane-1,5-diyl, pentane-2,3 -diyl, pentane-2,2-diyl, 1-methyl-butane-1,1-diyl, 1-methyl-butane-1,2-diyl, 1-methyl-butane-1,3-diyl, 1-methyl -butane-1,4-diyl, 2-methyl-butane-1,1-diyl, 2-methyl-butane-1,2-diyl, 2-methyl-butane-1,3-diyl, 2-methyl-butane -1,4-diyl, 2,2-dimethyl-propane-1,1-diyl, 2,2-dimethyl-propane-1,3-diyl, 1,1-dimethyl-propane-1,3-diyl, 1 , 1-Dimethyl-propane-1,2-diyl, 2,3-dimethyl-propane-1,3-diyl, 2,3-dimethyl-propane-1,2-diyl, 1,3-dimethyl-propane-1 , 3-diyl, hexane-1,1-diyl, hexane-1,2-diyl, hexane-1,3-diyl, hexane-1,4-diyl, hexane-1,5-diyl, hexane-1, 6-diyl, hexane-2,5-diyl, 2-methylpentane-1,1 -diyl, 1-methylpentane-1,2-diyl, 1-methylpentane-1,3-diyl, 1-methylpentane-1,4-diyl, 1-methylpentane-1,5-diyl , 2-methylpentane-1,1-diyl, 2-methylpentane-1,2-diyl, 2-methylpentane-1,3-diyl, 2-methylpentane-1,4-diyl, 2nd -Methylpentane-1,5-diyl, 3-methylpentane-1,1-diyl, 3-methylpentane-1,2-diyl, 3-methylpentane-1,3-diyl, 3-methyl -pentane-1,4-diyl, 3-methylpentane-1,5-diyl, 1,1-dimethylbutane-1,2-diyl, 1,1-dimethylbutane-1,3-diyl, 1 , 1-Dimethyl-butane-1,4-diyl, 1,2-dimethyl-butane-1,1-diyl, 1,2-dimethyl-butane-1,2-diyl, 1,2-dimethyl-butane-1 , 3-diyl, 1,2-dimethylbutane-1,4-diyl, 1,3-dimethylbutane-1,1-diyl, 1,3-dimethylbutane-1,2-diyl, 1,3 -Dimethyl-butane-1,3-diyl, 1,3-dimethyl-butane-1,4-diyl, 1-ethyl-butane-1,1-diyl, 1-ethyl-butane-1,2-diyl, 1 -Ethyl-butane-1,3-diyl, 1-ethyl-butane-1,4-diyl, 2-ethyl-butane-1,1-diyl, 2-ethyl-butane-1,2-diyl, 2-ethyl -butane-1,3-diyl, 2-ethyl-butane-1,4-diyl, 2-ethyl-butane-2,3-diyl, 2,2-dimethyl-butane-1,1-diyl, 2,2 -Dimethyl-butane-1,3-diyl, 2,2-dimethyl-butane-1,4-diyl, 1-isop ropyl-propane-1,1-diyl, 1-isopropyl-propane-1,2-diyl, 1-isopropyl-propane-1,3-diyl, 2-isopropyl-propane-1,1-diyl, 2-isopropyl- propane-1,2-diyl, 2-isopropyl-propane-1,3-diyl, 1,2,3-trimethyl-propane-1,1-diyl, 1,2,3-trimethyl-propane-1,2- diyl or 1,2,3-trimethyl-propane-1,3-diyl;
• - C ₃ -C ₆ cycloalkyl, and the cycloalkyl parts of C ₃ -C ₆ cycloalkylamino and C ₃ -C ₆ cycloalkylcarbonyl: z. B. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
• - heterocyclyl, and Heterocyclylteile of heterocyclyloxy, heterocyclylcarbonyl, heterocyclyl-C ₁ -C ₄ -alkyl, heterocyclyl-C ₁ -C ₆ alkyl, heterocyclylsulfonyl or Heterocyclyloxysulfonyl, heterocyclyloxycarbonyl, Heterocyclyloxythiocarbonyl, heterocyclyl-C ₂ -C ₆ alkenylcarbonyl, heterocyclylcarbonyl C ₁ -C ₆ alkyl, N- (C ₁ -C ₆ alkyl) -N- (heterocyclyl) aminocarbonyl, heterocyclylaminocarbonyl: a saturated, partially saturated or unsaturated 5- or 6-membered heterocyclic ring which comprises a contains two, three or four identical or different heteroatoms, selected from the following group: oxygen, sulfur or nitrogen, B. C-linked 5-membered rings such as:
  Tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, tetrahydropyrrol-2-yl, tetrahydropyrrol-3-yl, 2,3-dihydrofuran-2-yl, 2,3- Dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 4,5-dihydrofuran-2-yl, 4,5-dihydrofuran-3-yl, 2,3- Dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,5-dihydrothien-2 yl, 2,5-dihydrothien-3-yl, 4,5-dihydrothien-2-yl, 4,5-dihydrothiene -3-yl, 2,3-dihydro-1H-pyrrol-2-yl, 2,3-dihydro-1H-pyrrol-3-yl, 2,5-dihydro-1H-pyrrol-2-yl, 2,5 Dihydro-1H-pyrrol-3-yl, 4,5-dihydro-1H-pyrrol-2-yl, 4,5-dihydro-1H-pyrrol-3-yl, 3,4-dihydro-2H-pyrrol-2 -yl, 3,4-dihydro-2H-pyrrol-3-yl, 3,4-dihydro-5H-pyrrol-2-yl, 3,4-dihydro-5H-pyrrol-3-yl, 2-furyl, 3 Furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl, pyrrol-3-yl, tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydroisoxazol-3-yl, tetrahydroisoxazol-4-yl, tetrahydroisoxazole -yl, 1,2-oxathiolan-3-yl, 1,2-oxathiolan-4-yl, 1,2-oxathiolan-5-yl, tetrahydroisothiazol-3-yl, tetrahydroisothiazol-4-yl, tetr ahydroisothiazol-5-yl, 1,2-dithiolan-3-yl, 1,2-dithiolan-4-yl, tetrahydroimidazol-2-yl, tetrahydroimidazol-4-yl, tetrahydrooxazol-2-yl, tetrahydrooxazol-4-yl, Tetrahydrooxazol-5-yl, tetrahydrothiazol-2-yl, tetrahydrothiazol-4-yl, tetrahydrothiazol-5-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-oxathiolan- 2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, 4,5-dihydro- 1H-pyrazol-3-yl, 4,5-dihydro-1H-pyrazol-4-yl, 4,5-dihydro-1H-pyrazol-5-yl, 2,5-dihydro-1H-pyrazol-3-yl, 2,5-dihydro-1H-pyrazol-4-yl, 2,5-dihydro-1H-pyrazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4, 5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-5-yl, 2,3-dihydroisoxazol-3-yl, 2, 3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl, 2, 5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydroisothiazol-3-yl, 2 , 3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl, Δ ³ -1,2-dithiol-3-yl, Δ ³ -1,2-dithiol-4-yl, Δ ³ -1, 2-dithiol-5-yl, 4,5-dihydro-1H-imidazol-2-yl, 4,5-dihydro-1H-imidazol-4-yl, 4,5-dihydro-1H-imidazol-5-yl, 2,5-dihydro-1H-imidazol-2-yl, 2,5-dihydro-1H-imidazol-4-yl, 2,5-dihydro-1H-imidazol-5-yl, 2,3-dihydro-1H- imidazol-2-yl, 2,3-dihydro-1H-imidazol-4-yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 1,3-dioxol-2-yl, 1,3-dioxol-4-yl, 1,3-dithiol-2-yl, 1,3-dithiol-4-yl, 1,3-oxathiol-2-yl, 1,3-oxathiol-4-yl, 1,3-oxathiol-5-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazo l-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazole 5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, 1,2,3-Δ ² -oxadiazolin-4-yl, 1,2,3-Δ ² -oxadiazolin-5- yl, 1,2,4-Δ ⁴ -oxadiazolin-3-yl, 1,2,4-Δ ⁴ -oxadiazolin-5-yl, 1,2,4-Δ ² -oxadiazolin-3-yl, 1,2 , 4-Δ ² -oxadiazolin-5-yl, 1,2,4-Δ ³ -oxadiazolin-3-yl, 1,2,4-Δ ³ -oxadiazolin-5-yl, 1,3,4-Δ ² -Oxadiazolin-2-yl, 1,3,4-Δ ² -oxadiazolin-5-yl, 1,3,4-Δ ³ -oxadiazolin-2-yl, 1,3,4-oxadiazolin-5-yl, 1 , 2,4-Δ ⁴ -thiadiazolin-3-yl, 1,2,4-Δ ⁴ -thiadiazolin-5-yl, 1,2,4-Δ ³ -thiadiazolin-3-yl, 1,2,4- Δ ³ -Thiadiazolin-5-yl, 1,2,4-Δ ² -Thiadiazolin-3-yl, 1,2,4-Δ ² -Thiadiazolin-5-yl, 1,3,4-Δ ² -Thiadiazolin- 2-yl, 1,3,4-Δ ² -thiadiazolin-5-yl, 1,3,4-Δ ³ -thiadiazolin-2-yl, 1,3,4-thiadiazolin-2-yl, 1,3, 2-dioxathiolan-4-yl, 1,2,3-Δ ² triazolin-4-yl, 1,2,3-Δ ² triazolin-5-yl, 1,2,4-Δ ² triazolin-3 -yl, 1,2,4-Δ ² -Triazolin-5-yl, 1,2,4-Δ ³ -Triazolin-yl-3, 1,2,4- ³ -Triazolin-5-yl, 1,2,4-Δ ¹ -Triazolin-yl-2, 1,2,4-triazoline-3-yl, 3H-1,2,4-dithiazole-5-yl, 2H -1,3,4-dithiazol-5-yl, 2H-1,3,4-oxathiazol-5-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl , 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1st , 2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-y1, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazolyl-2-yl, 1,2, 3-triazol-4-yl, 1,2,4-triazol-3-yl, tetrazol-5-yl;
  C-linked 6-membered rings such as:
  Tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yloth, 4-yl, 2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydropyran-5-yl, 2H-3,4-dihydropyran-4-yl, 2H-3,4-dihydropyran-3- yl, 2H-3,4-dihydropyran-2-yl, 2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydrothiopyran-5-yl, 2H-3,4-dihydrothiopyran-4-yl, 2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl, 1,2,3,4-tetrahydropyridin-6-yl, 1,2,3,4-tetrahydropyridin-5- yl, 1,2,3,4-tetrahydropyridin-4-yl, 1,2,3,4-tetrahydropyridin-3-yl, 1,2,3,4-tetrahydropyridin-2 yl, 2H-5,6-dihydropyran -2-yl, 2H-5,6-dihydropyran-3-yl, 2H-5,6-dihydropyran-4-yl, 2H-5,6-dihydropyran-5-yl, 2H-5,6-dihydropyran-6 -yl, 2H-5,6-dihydrothiopyran-2-yl, 2H-5,6-dihydrothiopyran-3-yl, 2H-5,6-dihydrothiopyran-4-yl, 2H-5,6-dihydrothiopyran-5-yl , 2H-5,6-Dihydrothiopyran-6-yl, 1,2,5,6-tetrahydropyridin-2-yl, 1,2,5,6-tetrahydropyridin-3-yl, 1,2,5,6-tetrahydropyridine -4-yl, 1,2, 5,6-tetrahydropyridin-5-yl, 1,2,5,6-tetrahydropyridin-6-yl, 2,3,4,5-tetrahydropyridin-2-yl, 2,3,4,5-tetrahydropyridin-3- yl, 2,3,4,5-tetrahydropyridin-4-yl, 2,3,4,5-tetrahydropyridin-5-yl, 2,3,4,5-tetrahydropyridin-6-yl, 4H-pyran-2- yl, 4H-pyran-3-yl, 4H-pyran-4-yl, 4H-thiopyran-2-yl, 4H-thiopyran-3-yl, 4H-thiopyran-4-yl, 1,4-dihydropyridin-2- yl, 1,4-dihydropyridin-3-yl, 1,4-dihydropyridin-4-yl, 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran 5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopyran-5-yl, 2H-thiopyran-6- yl, 1,2-dihydropyridin-2-yl, 1,2-dihydropyridin-3-yl, 1,2-dihydropyridin-4-yl, 1,2-dihydropyridin-5-yl, 1,2-dihydropyridin-6- yl, 3,4-dihydropyridin-2-yl, 3,4-dihydropyridin-3-yl, 3,4-dihydropyridin-4 yl, 3,4-dihydropyridin-5-yl, 3,4-dihydropyridin-6-yl , 2,5-dihydropyridin-2-yl, 2,5-dihydropyridin-3-yl, 2,5-dihydropyridin-4-yl, 2,5-dihydropyridin-5-yl, 2,5-dihydropyridin-6-yl , 2,3-dihydropyridin-2-yl, 2,3-dihydropyridin-3-yl, 2,3-dihy dropyridin-4-yl, 2,3-dihydropyridin-5-yl, 2,3-dihydropyridin-6 yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, 1,3-dioxan-2 -yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 1,3-dithian-2-yl, 1,3-dithian-4 -yl, 1,3-dithian-5-yl, 1,4-dithian-2-yl, 1,3-oxathian-2-yl, 1,3-oxathian-4-yl, 1,3-oxathian-5 -yl, 1,3-oxathian-6-yl, 1,4-oxathian-2-yl, 1,4-oxathian-3-yl, 1,2-dithian-3-yl, 1,2-dithian-4 -yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, hexahydropyrazin-2-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, tetrahydro-1,3-oxazin-2-yl , Tetrahydro-1,3-oxazin-4-yl, tetrahydro-1,3-oxazin-5-yl, tetrahydro-1,3-oxazin-6-yl, tetrahydro-1,3-thiazin-2-yl, tetrahydro -1,3-thiazin-4-yl, tetrahydro-1,3-thiazin-5-yl, tetrahydro-1,3-thiazin-6-yl, tetrahydro-1,4-thiazin-2-yl, tetrahydro-1 , 4-thiazin-3-yl, tetrahydro-1,4-oxazin-2-yl, tetrahydro-1,4-oxazin-3-yl, tetrahydro-1,2-oxazin-3-yl, tetrahydro-1,2 -oxazin-4-yl, tetrahydro-1,2-oxazin-5-yl, tetrahydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-oxazin-3-yl, 2H-5,6-dihydro-1,2-oxazin-4-yl, 2H-5,6-dihydro-1,2-oxazin- 5-yl, 2H-5,6-dihydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-thiazin-3-yl, 2H-5,6-dihydro-1, 2-thiazin-4-yl, 2H-5,6-dihydro-1,2-thiazin-5-yl, 2H-5,6-dihydro-1,2-thiazin-6-yl, 4H-5,6- Dihydro-1,2-oxazin-3-yl, 4H-5,6-dihydro-1,2-oxazin-4-yl, 4H-5,6-dihydro-1,2-oxazin-5-yl, 4H- 5,6-dihydro-1,2-oxazin-6-yl, 4H-5,6-dihydro-1,2-thiazin-3-yl, 4H-5,6-dihydro-1,2-thiazin-4- yl, 4H-5,6-dihydro-1,2-thiazin-5-yl, 4H-5,6-dihydro-1,2-thiazin-6-yl, 2H-3,6-dihydro-1,2- oxazin-3-yl, 2H-3,6-dihydro-1,2-oxazin-4-yl, 2H-3,6-dihydro-1,2-oxazin-5-yl, 2H-3,6-dihydro- 1,2-oxazin-6-yl, 2H-3,6-dihydro-1,2-thiazin-3-yl, 2H-3,6-dihydro-1,2-thiazin-4-yl, 2H-3, 6-dihydro-1,2-thiazin-5-yl, 2H-3,6-dihydro-1,2-thiazin-6-yl, 2H-3,4-dihydro-1,2-oxazin-3-yl, 2H-3,4-dihydro-1,2-oxazin-4-yl, 2H-3,4-dihydro-1,2-oxazin-5-yl, 2H-3,4-dihydro-1,2-oxazin- 6-yl, 2H-3,4-dihydro-1,2-thiazin-3-yl, 2H-3,4-dihydro-1,2-thiazin-4-yl, 211-3,4-dihydro-1, 2-thiaz in-5-yl, 2H-3,4-dihydro-1,2-thiazin-6-yl, 2,3,4,5-tetrahydropyridazin-3-yl, 2,3,4,5-tetrahydropyridazin-4- yl, 2,3,4,5-tetrahydropyridazin-5-yl, 2,3,4,5-tetrahydropyridazin-6-yl, 3,4,5,6-tetrahydropyridazin-3-yl, 3,4,5, 6-tetrahydropyridazin-4-yl, 1,2,51 6-tetrahydropyridazin-3-yl, 1,2,5,6-tetrahydropyridazin-4-yl, 1,2,5,6-tetrahydropyridazin-5-yl, 1 , 2,5,6-tetrahydropyridazin-6-yl, 1,2,3,6-tetrahydropyridazin-3-yl, 1,2,3,6-tetrahydropyridazin-4-yl, 4H-5,6-dihydro-1 , 3-oxazin-2-yl, 4H-5,6-dihydro-1,3-oxazin-4-yl, 4H-5,6-dihydro-1,3-oxazin-5-yl, 4H-5.6 Dihydro-1,3-oxazin-6-yl, 4H-5,6-dihydro-1,3-thiazin-2-yl, 4H-5,6-dihydro-1,3-thiazin-4-yl, 4H -5,6-dihydro-1,3-thiazin-5-yl, 4H-5,6-dihydro-1,3-thiazin-6-yl, 3,4,5,6-tetrahydropyrimidin-2-yl, 3rd , 4,5,6-tetrahydropyrimidin-4-yl, 3,4,5,6-tetrahydropyrimidin-5-yl, 3,4,5,6-tetrahydropyrimidin-6-yl, 1,2,3,4-tetrahydropyrazine -2-yl, 1,2,3,4-tetrahydropyrazin-5-yl, 1,2,3,4-tetrahydropyrimidin-2-yl, 1,2,3,4-tetrahydropyrimidin-4-yl, 1,2 , 3,4-tetrahydropyr imidin-5-yl, 1,2,3,4-tetrahydropyrimidin-6-yl, 2,3-dihydro-1,4-thiazin-2-yl, 2,3-dihydro-1,4-thiazin-3- yl, 2,3-dihydro-1,4-thiazin-5-yl, 2,3-dihydro-1,4-thiazin-6-yl, 2H-1,2-oxazin-3-yl, 2H-1, 2-oxazin-4-yl, 2H-1,2-oxazin-5-yl, 2H-1,2-oxazin-6-yl, 2H-1,2-thiazin-3-yl, 2H-1,2- Thiazin-4-yl, 2H-1,2-thiazin-5-yl, 2H-1,2-thiazin-6-yl, 4H-1,2-oxazin-3-yl, 4H-1,2-oxazin- 4-yl, 4H-1,2-oxazin-5-yl, 4H-1,2-oxazin-6-yl, 4H-1,2-thiazin-3-yl, 4H-1,2-thiazin-4- yl, 4H-1,2-thiazin-5-yl, 4H-1,2-thiazin-6-yl, 6H-1,2-oxazin-3-yl, 6H-1,2-oxazin-4-yl, 6H-1,2-oxazin-5-yl, 6H-1,2-oxazin-6-yl, 6H-1,2-thiazin-3-yl, 6H-1,2-thiazin-4-yl, 6H- 1,2 thiazin-5-yl, 6H-1,2-thiazin-6-yl, 2H-1,3-oxazin-2-yl, 2H-1,3-oxazin-4-yl, 2H-1,3 -Oxazin-5-yl, 2H-1,3-oxazin-6-yl, 2H-1,3-thiazin-2-yl, 2H-1,3-thiazin-4-yl, 2H-1,3-thiazine -5-yl, 2H-1,3-thiazin-6-yl, 4H-1,3-oxazin-2-yl, 4H-1,3-oxazin-4-yl, 4H-1,3-oxazin-5 -yl, 4H-1,3-oxazin-6-yl, 4H-1,3-thiazin-2-yl, 4H-1,3-thiazin-4-yl, 4H-1,3-thiazin-5-yl , 4H-1,3-thiazin-6-yl, 6H-1,3-oxazine -2-yl, 6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-oxazin-6-yl, 6H-1,3-thiazin-2 -yl, 6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-thiazin-6-yl, 2H-1,4-oxazin-2-yl , 2H-1,4-oxazin-3-yl, 2H-1,4-oxazin-5-yl, 2H-1,4-oxazin-6-yl, 2H-1,4-thiazin-2-yl, 2H -1,4-thiazin-3-yl, 2H-1,4-thiazin-5-yl, 2H-1,4-thiazin-6-yl, 4H-1,4-oxazin-2-yl, 4H-1 , 4-oxazin-3-yl, 4H-1,4-thiazin-2-yl, 4H-1,4-thiazin-3-yl, 1,4-dihydropyridazin-3-yl, 1,4-dihydropyridazin-4 -yl, 1,4-dihydropyridazin-5-yl, 1,4-dihydropyridazin-6-yl, 1,4-dihydropyrazin-2-yl, 1,2-dihydropyrazin-2-yl, 1,2-dihydropyrazin-3 -yl, 1,2-dihydropyrazin-5-yl, 1,2-dihydropyrazin-6-yl, 1,4-dihydropyrimidin-2-yl, 1,4-dihydropyrimidin-4-yl, 1,4-dihydropyrimidin-5 -yl, 1,4-dihydropyrimidin-6-yl, 3,4-dihydropyrimidin-2-yl, 3,4-dihydropyrimidin-4-yl, 3,4-dihydropyrimidin-5-yl, 3,4-dihydropyrimidin-6 -yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, 1,3,5-triazin-2-yl , 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1, 2,4-triazin-6-yl or 1,2,4,5-tetrazin-3-yl;
  N-linked 5-membered rings such as:
  Tetrahydropyrrol-1-yl, 2,3-dihydro-1H-pyrrol-1-yl, 2,5-dihydro-1H-pyrrol-1-yl, pyrrol-1-yl, tetrahydropyrazol-1-yl, tetrahydroisoxazol-2- yl, tetrahydroisothiazol-2-yl, tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl, tetrahydrothiazol-3-yl, 4,5-dihydro-1H-pyrazol-1-yl, 2,5-dihydro-1H-pyrazol- 1-yl, 2,3-dihydro-1H-pyrazol-1-yl, 2,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-2-yl, 2,5-dihydroisothiazol-2-yl, 2, 3-dihydroisoxazol-2-yl, 4,5-dihydro-1H-imidazol-1-yl, 2,5-dihydro-1H-imidazol-1-yl, 2,3-dihydro-1H-imidazol-1-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrothiazol-3-yl, pyrazol-1-yl, imidazol-1-yl, 1,2,4-Δ ⁴ -oxadiazolin-2-yl, 1,2 , 4-Δ ² -oxadiazolin-4-yl, 1,2,4-Δ ³ -oxadiazolin-2-yl, 1,3,4-Δ ² -oxadiazolin-4-yl, 1,2,4-Δ ⁵ -Thiadiazolin-2-yl, 1,2,4-Δ ³ -Thiadiazolin-2-yl, 1,2,4-Δ ² -Thiadiazolin-4-yl, 1,3,4-Δ ² -Thiadiazolin-4- yl, 1,2,3-Δ ² triazolin-1-yl, 1,2,4-Δ ² triazolin-1-yl, 1,2,4-Δ ² triazolin-4-yl, 1,2 , 4-Δ ³ -triazolin-1-yl, 1,2,4-Δ ¹ -triazolin-4-yl, 1,2,3-triazol-1 -yl, 1,2,4-triazol-1-yl, tetrazol-1-yl;
  N-linked 6-membered rings such as:
  Piperidin-1-yl, 1,2,3,4-tetrahydropyridin-1-yl, 1,2,5,6-tetrahydropyridin-1-yl, 1,4-dihydropyridin-1-yl, 1,2-dihydropyridin 1-yl, hexahydropyrimidin-1-yl, hexahydropyrazin-1-yl, hexahydropyridazin-1-yl, tetrahydro-1,3-oxazin-3-yl, tetrahydro-1,3-thiazin-3-yl, tetrahydro-1, 4-thiazin-4-yl, tetrahydro-1,4-oxazin-4-yl (morpholinyl), tetrahydro-1,2-oxazin-2-yl, 2H-5,6-dihydro-1,2-oxazin-2 -yl, 2H-5,6-dihydro-1,2-thiazin-2-yl, 2H-3,6-dihydro-1,2-oxazin-2-yl, 2H-3,6-dihydro-1,2 -thiazin-2-yl, 2H-3,4-dihydro-1,2-thiazin-2-yl, 2,3,4,5-tetrahydropyridazin-2-yl, 1,2,5,6-tetrahydropyridazin-1 -yl, 1,2,5,6-tetrahydropyridazin-2-yl, 1,2,3,6-tetrahydropyridazin-1-yl, 3,4,5,6-tetrahydropyrimidin-3-yl, 1,2,3 , 4-tetrahydropyrazin-1-yl, 1,2,3,4-tetrahydropyrimidin-1-yl, 1,2,3,4-tetrahydropyrimidin-3-yl, 2,3-dihydro-1,4-thiazin-4 -yl, 2H-1,2-oxazin-2-yl, 2H-1,2-thiazin-2-yl, 4H-1,4-oxazin-4-yl, 4H-1,4-thiazin-4-yl , 1,4-dihydropyridazin-1-yl, 1,4-dihydropyrazin-1-yl, 1,2-dihydropyrazin-1-yl, 1,4-dihydropyrimidi n-1-yl or 3,4-dihydropyrimidin-3-yl;
  as well as N-linked cyclic imides such as:
  Phthalimide, tetrahydrophthalimide, succinimide, maleimide, glutarimide, 5-oxotriazolin-1-yl, 5-oxo-1,3,4-oxadiazolin-4-yl or 2,4-dioxo- (1H, 3H) -pyrimidine- 3-yl;
  a bicyclic ring system can be formed with a fused-on phenyl ring or with a C ₃ -C ₆ carbocycle or a further 5- to 6-membered heterocycle,
  where appropriate the sulfur of the heterocycles mentioned can be oxidized to S = O or S (= O) ₂
  and a bicyclic ring system can be formed with a fused phenyl ring or with a C ₃ -C ₆ carbocycle or with a further 5- to 6-membered heterocycle.

All phenyl rings or heterocyclyl residues as well as all Phenyl components in phenoxy, phenylalkyl, phenylcarbonylalkyl, Phenylcarbonyl, phenylalkenylcarbonyl, phenoxycarbonyl, Phenyloxythiocarbonyl, phenylaminocarbonyl and N-alkyl-N-phenylaminocarbonyl, phenylsulfonyl or Phenoxysulfonyl or heterocyclyl components in heterocyclyloxy, Heterocyclylalkyl, heterocyclylcarbonylalkyl, Heterocyclylcarbonyl, heterocyclyloxythiocarbonyl, Heterocyclylalkenylcarbonyl, heterocyclyloxycarbonyl, Heterocyclylaminocarbonyl, N-alkyl-N-heterocyclylaminocarbonyl, Heterocyclylsulfonyl or heterocyclyloxysulfonyl are so far not stated otherwise, preferably unsubstituted or worn one, two or three halogen atoms and / or a nitro group, one Cyano residue and / or one or two methyl, trifluoromethyl, Methoxy or trifluoromethoxy substituents.  

With regard to the use of the compounds of the formula I according to the invention as herbicides, the variables X, R ¹ , R ² , R ³ and R ¹⁷ preferably have the following meanings, in each case individually or in combination:
XO, S, SO ₂ , NR ¹ or N-NR ¹ R ¹⁷ ;
R ^{1 is} hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ - Haloalkyl sulfonyl, C ₁ -Ce alkylcarbonyl, C ₁ -C ₆ haloalkylcarbonyl,
C ₃ -C ₆ cycloalkyl, phenyl, heterocyclyl, phenylsulfonyl, heterocyclylsulfonyl, phenylcarbonyl, heterocyclylcarbonyl, phenyl-C ₁ -C ₆ -alkyl, heterocyclyl-C ₁ -C ₆ -alkyl,
where the phenyl, heterocyclyl and cycloalkyl radicals of the aforementioned groups can optionally be substituted in the manner described above and, for example, one, two or three substituents selected from halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylcarbonyl, nitro, hydroxy or cyano, preferably selected from halogen, C ₁ -C ₄ alkyl, nitro or cyano; phenyl, heterocyclyl,
R ² halogen, especially fluorine or chlorine, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, especially methylsulfonyl;
R ^{3 is} hydrogen, fluorine or chlorine, especially hydrogen;
R ^{17 is} hydrogen or C ₁ -C ₄ alkyl, in particular hydrogen or methyl.

Hex in formula I preferably represents a radical of formula IIa.

In R ¹ , heterocyclyl is preferably unsaturated, aromatic heterocyclyl, which is especially C-bonded.

In particular, R ^{1 is} C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ cycloal kyl, C ₁ -C ₄ alkylsulfonyl, phenyl, phenyl-C ₁ -C ₄ alkyl or Phenyl sulfonyl, where the phenyl ring of the three latter groups may be substituted in the manner described above and in particular in the 4-position may be halogen or C _{1 60397 00070 552 001000280000000200012000285916028600040 0002019929259 00004 60278} -C ₄ -alkyl.

Examples of particularly preferred radicals R ¹ are: methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, cyclopropyl, phenyl, 4-methylphenyl, 4-chlorophenyl , Benzyl, 1- and 2-phenylethyl, methyl, ethylsulfonyl, phenylsulfonyl, 4-methylphenylsulfonyl and 4-chlorophenylsulfonyl.

In N-NR ¹ R ¹⁷ , R ¹ and R ¹⁷ preferably have the following meanings:
R ¹ C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ alkylsulfonyl, phenyl, phenyl-C ₁ -C ₄ alkyl or phenylsulfonyl, where the phenyl ring of the latter three groups can be substituted in the 4-position with halogen or C ₁ -C ₄ alkyl,
R ^{17 is} hydrogen or C ₁ -C ₄ alkyl.

NR ¹ R ¹⁷ particularly preferably represents C ₁ -C ₄ -alkylamino, di-C ₁ -C ₄ -alkylamino, phenyl-C ₁ -C ₄ -alkylamino.

R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ preferably have the following meanings:
R ⁴ hydroxy, mercapto, halogen, OR ¹¹ , SR ¹¹ , SO ₂ R ¹² , OSO ₂ R ¹² , NR ¹⁵ R ¹⁶ and N-linked nitrogen heterocyclyl, which can be partially or completely halogenated and / or one or two or can carry three of the following radicals: nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy; wherein R ¹¹ , R ¹² , R ¹⁵ and R ^{16 have} the meanings given above and in particular the meanings given below; R ⁴ stands in particular for hydroxy, C ₁ -C ₄ alkylcarbonyloxy, C ₁ -C ₄ alkylamino, di-C ₁ -C ₄ alkylamino, C ₁ -C ₄ alkyl thio, N- (C ₁ -C _4- alkyloxy) -N- (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkylsulfonyloxy, phenylthio, phenylsulfonyl, phenylsulfonyloxy and N-linked heterocyclyl, where the phenyl group and the heterocyclyl group of the latter four substituents with halogen , Nitro, cyano or C ₁ -C ₄ -alkyl may be substituted, the phenyl group may preferably be substituted in the 4-position with halo or C ₁ -C ₄ -alkyl; Examples for R ⁴ are hydroxy, acetyl, methylsulfonyl, methylsulfonyloxy, phenylthio, 4-methylphenylthio, 4-chlorophenylthio, phenylsulfonyl, 4-methylphenylsulfonyl, 4-chlorophenylsulfonyl, phenylsulfonyloxy, 4-methylphenylsulfonyloxamino, 4-chlorophenylamino, 4-chlorophenylamino, 4-chlorophenylamino -Methoxy-N-methylamino, N-ethoxy-N-methylamino, N-methoxy-N-ethylamino, N-ethoxy-N-ethylamino, N-morpholine, N-pyrrolidine and N-piperidine;
R ⁵ , R ^{9 are} hydrogen or C ₁ -C ₄ alkyl, such as methyl, ethyl or propyl; especially hydrogen or methyl;
R ⁶ , R ⁸ , R ^{10 are} hydrogen or C ₁ -C ₄ alkyl, such as methyl, ethyl or propyl; especially hydrogen or methyl;
R ^{7 is} hydrogen, hydroxy, C ₁ -C ₆ alkyl, di (C ₁ -C ₆ alk oxy) methyl, (C ₁ -C ₆ alkoxy) - (C ₁ -C ₆ alkylthio) methyl , Di- (C ₁ -C ₆ alkylthio) methyl, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C _6- alkylsulfonyl or C ₁ -C ₆ -haloalkylsulfonyl;
1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-dithian-2-yl, where the six latter radicals can be substituted by one, two or three C ₁ -C ₄ -alkyl radicals;
in particular hydrogen, hydroxy or C ₁ -C ₄ alkyl, such as methyl, ethyl or propyl; or
R ⁶ and R ⁸ or R ⁸ and R ¹⁰ together form a π bond or a C ₃ -C ₅ alkyl chain which can carry one to three radicals from the following group: halogen, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ alkoxy carbonyl, from; or
R ⁶ and R ¹⁰ or R ⁵ and R ⁹ together form a C ₁ -C ₄ alkyl chain which can carry one to three radicals from the following group: halogen, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ -haloalkyl or C ₁ -C ₄ alkoxycarbonyl, from; or
R ⁷ and R ⁸ together form a -O- (CH ₂ ) _p -O-, -O- (CH ₂ ) _p -S- or -S- (CH ₂ ) _p -S chain, which is represented by one to three Radicals from the following group can be substituted: halogen, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ alkoxycarbonyl; or
R ⁷ and R ⁸ together with the carbon to which they are bound form a carbonyl group. The variable p is preferably 2 or 3 and the variable q is preferably 2, 3 or 4.

In R ⁴ , heterocyclyl is preferably saturated, N-bonded nes heterocyclyl, in particular monocyclic, 5- or 6-ring he trocyclyl, which optionally contains a further hetroatome, e.g. B. acid or sulfur, imino or C ₁ -C ₆ alkylimino in the ring.

Preferred meanings for R ¹¹ to R ¹⁶ are:
R ^{11 is} C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, C ₁ -C ₆ alkylcarbonyl, C ₂ -C ₆ alkenylcarbonyl, C ₃ -C ₆ cycloalkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, C ₃ -C ₆ alkenyloxycarbonyl, C ₃ -C ₆ alkynyloxycarbonyl, C ₁ -C ₆ alkylthiocarbonyl, C ₁ -C ₆ alkylaminocarbonyl, C ₃ -C ₆ -Alkenylaminocarbonyl, C ₃ -C ₆ -alkynylaminocarbonyl, N, N-Di (C ₁ -C ₆ -alkyl) aminocarbonyl, N- (C ₃ -C ₆ -alken yl) -N- (C ₁ -C _6- alkyl) -aminocarbonyl, N- (C ₃ -C ₆ -alkynyl) -N- (C ₁ -C ₆ -alkyl) -aminocarbonyl, N- (C ₁ -C ₆ -alkoxy) -N- ( C ₁ -C ₆ alkyl) aminocarbonyl, N- (C ₃ -C ₆ alkene yl) -N- (C ₁ -C ₆ alkoxy) aminocarbonyl, N- (C ₃ -C ₆ alkynyl) -N- (C ₁ -C ₆ -alkoxy) -aminocarbonyl, di- (C ₁ -C ₆ -alk yl) -aminothiocarbonyl, C ₁ -C ₆ -alkoxyimino-C ₁ -C ₆ -alkyl, where mentioned Alkyl, cycloalkyl or alkoxy radicals can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylth io, Di- (C ₁ -C ₄ alkyl) - amino, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkoxycarbonyl, hydroxy carbonyl, C ₁ -C ₄ alkylaminocarbonyl, di- (C ₁ -C _4- alkyl) amino carbonyl, C ₁ -C ₄ alkylcarbonyloxy or C ₃ -C ₆ cycloalkyl;
Phenyl, phenyl-C ₁ -C ₆ -alkyl, phenylcarbonyl-C ₁ -C ₆ -alkyl, phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl, phenyl-C ₂ -C ₆ -alkenylcarbonyl, heterocyclyl, heterocyclyl-C ₁ -C ₆ -alkyl , Heterocyclylcarbonyl-C ₁ -C ₆ -alkyl, Heter rocyclylcarbonyl, Heterocyclyloxycarbonyl, Heterocyclylo xythiocarbonyl or Heterocyclyl-C ₁ -C ₆ -alkenylcarbonyl, where the phenyl or the heterocyclyl radical of the latter 14 may be partially and completely halogenated or can carry one to three of the following radicals: nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy; in particular C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkyl aminocarbonyl or N, N-Di (C ₁ -C ₆ alkyl) aminocarbonyl, where the alkyl or alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, C ₁ -C ₄ - Alkoxy, C ₁ -C ₄ alkylthio or C ₁ -C ₄ alkoxycarbonyl;
Phenyl, phenyl-C ₁ -C ₆ -alkyl, phenylcarbonyl-C ₁ -C ₆ -alkyl, phenylcarbonyl, phenoxycarbonyl, heterocyclyl-, heterocyclyl-C ₁ -C ₆ -alkyl, heterocyclylcarbonyl-C ₁ -C ₆ -alkyl, Hete rocyclylcarbonyl or heterocyclyloxycarbonyl, where the phenyl or the heterocyclyl radical of the 10 last-mentioned substituents can be partially or completely halogenated or / or can carry one to three of the following radicals: nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy;
R ^{12 is} C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ cycloalkyl, where the three radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: Cyano, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl thio, C ₁ -C ₄ alkylcarbonyl or C ₁ -C ₄ alkoxycarbonyl;
Phenyl, phenyl-C ₁ -C ₄ -alkyl, heterocyclyl or heterocyclyl-C ₁ -C ₄ -alkyl, where the phenyl or heterocyclyl radical of the four last-mentioned substituents can be partially or completely halogenated and / or one to three of the can carry the following radicals: nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ alkoxycarbonyl;
R ¹³ , R ¹⁴ hydroxy, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, phenyl, phenyl-C ₁ -C ₄ alkyl or phenoxy, where the latter three substituents can be partially or completely halogenated and / or may carry one to three of the following radicals: nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ -halogen alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ -haloalkoxy or C ₁ -C ₄ alkoxycarbonyl;
R ^{15 is} C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ alkenyloxy or Di- (C ₁ -C ₆ alkyl) amino, where the alkyl, cycloalkyl or alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following radicals: cyano, C ₁ -C ₄ Alkoxycarbonyl, C ₁ -C ₄ alkylaminocarbonyl, di (C ₁ -C ₄ alkyl) aminocarbonyl or C ₃ -C ₆ cycloalkyl;
Phenyl, phenyl-C ₁ -C ₄ -alkyl, phenylcarbonyl, heterocyclyl, heterocycly-C ₁ -C ₄ -alkyl or heterocyclylcarbonyl, where the phenyl or heterocyclyl radical of the six last-mentioned substituents can be partially or completely halogenated and / or may carry one to three of the following radicals: nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ -halogen alkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ -haloalkoxy;
R ^{16 is} C ₁ -C ₆ alkyl or C ₃ -C ₆ alkenyl.

The compounds of the formula I are extremely preferred, where the variables in the formula IIa or IIb, independently of one another or in combination with one another, have the following meanings:
R ⁵ , R ^{9 are} hydrogen or C ₁ -C ₄ alkyl;
R ⁶ , R ⁸ , R ^{10 are} hydrogen or C ₁ -C ₄ alkyl;
R ^{7 is} hydrogen, hydroxy, C ₁ -C ₆ alkyl, in particular C ₁ -C ₄ alkyl, di- (C ₁ -C ₆ alkoxy) methyl, (C ₁ -C ₆ alkoxy) - (C ₁ -C ₆ -alkylthio) -methyl, di- (C ₁ -C ₆ -alkylthio) -methyl, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -haloalkylthio, C ₁ -C ₆ -alkylsulfonyl or C ₁ - C ₆ haloalkylsulfonyl; in particular hydrogen, hydroxy or C ₁ -C ₆ alkyl; or
R ⁵ and R ⁹ or R ⁶ and R ¹⁰ together form a C ₁ -C ₄ alkyl chain which can carry one to three radicals from the following group: halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ - Halogen alkyl; in particular R ⁶ and R ¹⁰ together form a methylene or an ethylene bridge which can carry one or two radicals from the following group: halogen, C ₁ -C ₂ alkyl or C ₁ -C ₂ haloalkyl; or
R ⁷ and R ⁸ together with the carbon to which they are bound form a carbonyl group.

Compounds of the formula I in which
R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ independently of one another represent hydrogen or C ₁ -C ₄ alkyl,
R ^{7 can} also be hydroxyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, Ha logenalkoxy or haloalkylthio, or
R ⁷ and R ⁸ together with the carbon atom to which they are attached also form a carbonyl group, a 1,3-dioxolane, 1,3-dithiolane, 1,3-oxothiolane, 1,3-oxothiane, 1 , 3-dithiolane or a 1,3-dithiane ring, where the 2-position of the six rings mentioned is identical to the carbon atom to which R ¹¹ and R ^{12 are} bonded, and / or
R ⁵ and R ⁹ or R ⁶ and R ^{10 can} also mean a C ₁ -C ₄ alkylene chain, or
R ⁶ and R ⁸ or R ⁸ and R ⁹ together can form a π bond.

Compounds of the general formula I.1 are very particularly preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.1.1 to I.1.135).

Table A

Compounds of the general formula I.2 are also extremely preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.2.1 to I.2.135).

Compounds of the general formula I.3 are also extremely preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.3.1 to I.3.135).

Compounds of the general formula I.4 are also extremely preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.4.1 to I.4.135).

Compounds of the general formula I.5 are also very particularly preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.5.1 to I.5.135).

Compounds of the general formula I.6 are also extremely preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.6.1 to I.6.135).

Compounds of the general formula I.7 are also extremely preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.7.1 to I.7.135).

Compounds of the general formula I.8 are very particularly preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.1.8 to I.8.135).

Compounds of the general formula I.9 are also very particularly preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.9.1 to I.9.135).

Compounds of the general formula I.10 are also very particularly preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.10.1 to I.10.135).

Compounds of the general formula I.11 are also extremely preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.11.1 to I.11.135).

Compounds of the general formula I.12 are also extremely preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.12.1 to I.12.135).

Compounds of the general formula I.13 are also very particularly preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.13.1 to I.13.135).

Compounds of the general formula I.14 are also very particularly preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.14.1 to I.14.135).

Compounds of the general formula I.15 are also extremely preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.15.1 to I.15.135).

Compounds of the general formula I.16 are also very particularly preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.16.1 to I.16.135).

Compounds of the general formula I.17 are also extremely preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.17.1 to I.17.135).

Compounds of the general formula I.18 are also very particularly preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.18.1 to I.18.135).

Compounds of the general formula I.19 are also very particularly preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.19.1 to I.19.135).

Compounds of the general formula I.20 are also extremely preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.20.1 to I.20.135).

Compounds of the general formula I.21 are also very particularly preferred

wherein R ⁴ and X have the meaning given in one row of Table A (compounds I.21.1 to I.21.135).

The preparation of compounds of the formula I in which R ^{4 is} hydroxy is carried out by reacting an activated carboxylic acid IVb or a carboxylic acid IVa, which is preferably activated in situ, with a cyclohexane-1,3-dione of the formula III to which Acylation product and subsequent rearrangement.

L ¹ stands for a nucleophilically displaceable leaving group, such as Halo gene, for. B. bromine or chlorine, N-linked aromatic heterocy clyl, z. B. imidazolyl or pyridyl, carboxylate, e.g. B. acetate or trifluoroacetate etc.

The activated carboxylic acid IVb can be used directly, such as in the case of the benzoyl halides, or in situ from the carboxylic acid IVa are generated, e.g. B. with carbodiimides such as ethyl (3'-dimethyl aminopropyl) carbodiimide, dicyclohexylcarbodiimide, triphenyl phosphine / azodicarboxylic acid ester, 2-pyridine disulfide / triphenyl phosphine, carbonyldiimidazole etc.

The acylation reaction may be advantageous to be carried out in the presence of a base. The reactants and the Auxiliary base are expediently in equimolar amounts used. A slight excess of the auxiliary base, e.g. B. 1.2 to 1.5 Molar equivalents, based on IVa or IVb, can under certain circumstances be beneficial.

Suitable auxiliary bases are tertiary alkylamines, pyridine or Alkali metal carbonates. As a solvent, for. B. chlorinated Hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene or chlorine benzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetra hydrofuran or dioxane, polar aprotic solvents, such as Acetonitrile, dimethylformamide or dimethyl sulfoxide or ester such as ethyl acetate or mixtures thereof.

Halides are used as the activated carboxylic acid component sets, it may be appropriate when adding this reaction partners to cool the reaction mixture to about 0 to 10 ° C. On finally stirring at 20 to 100 ° C, preferably at 25 to 50 ° C until the reaction is complete. The processing takes place in the usual way, e.g. B. the reaction mixture is ge on water pour, the product of value extracted. Are suitable as solvents especially methylene chloride, diethyl ether and acetic acid ethyl ester. After drying the organic phase and removing the The crude ester can be solvent without further purification storage can be used.

The rearrangement of the esters to the compounds of formula I takes place expediently at temperatures of 20 to 100 ° C in one Solvent and in the presence of a base and optionally using a cyano compound as a catalyst.

As a solvent, for. B. acetonitrile, methylene chloride, 1,2-dichloroethane, dioxane, ethyl acetate, toluene or Ge mix of them can be used. Preferred solvents are Acetonitrile and dioxane.  

Suitable bases are tertiary amines such as triethylamine, aromatic Amines such as pyridine or alkali carbonates, such as sodium carbonate or Potassium carbonate, preferably in equimolar amounts or up to a fourfold excess, based on the ester become. Triethylamine or alkali carbonate are preferred used, preferably in double equimolar ratio in Terms of the ester.

Inorganic cyanides, such as sodium, come as cyano compounds cyanide or potassium cyanide and organic cyano compounds, such as Acetone cyanohydrin or trimethylsilyl cyanide. You who that in an amount of 1 to 50 mol%, based on the ester set. Acetone cyanohydrin or trimethyl are preferred silyl cyanide, e.g. B. in an amount of 5 to 15, preferably about 10 mol%, based on the ester, used.

Working up can be carried out in a manner known per se. The The reaction mixture is e.g. B. with dilute mineral acid, such as 5% Hydrochloric acid or sulfuric acid, acidified, with an organic Solvents, e.g. B. methylene chloride or ethyl acetate ex trahed. The organic extract can contain 5-10% alkali carbonate solution, e.g. B. sodium carbonate or potassium carbonate solution be extracted. The aqueous phase is acidified and the vacuumed precipitate and / or with methylene chloride or Extracted ethyl acetate, dried and concentrated.

The acylation of the carboxylic acid IVa or IVb and the following Rearrangement to compound I can also be called a "one-pot reaction", i.e. H. can be carried out without isolation of the ester.

• A) Compounds of the formula I with R ⁴ = halo are prepared by reacting cyclohexenone derivatives of the formula I (with R ⁴ = hydroxy) with halogenating agents:
  Here and below, "Ia" stands for a compound of the general formula I, in which hex represents a radical of the general formula IIa, and "Ib" correspondingly for a compound of the general formula I, in which hex represents a radical IIb.
  Suitable halogenating agents are, for example, phosgene, diphosgene, triphosgene, thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride, mesyl chloride, chloromethylene-N, N-dimethylammonium chloride, oxalyl bromide, phosphorus oxybromide etc.
• B) The preparation of compounds of the formula I with R ⁴ = OR ¹¹ , OSO ₂ R ¹² , OPOR ¹³ R ¹⁴ or OPSR ¹³ R ¹⁴ is carried out by reacting cyclohexenone derivatives of the formula I (with R ⁴ = hydroxy) with alkylation -, Sulfonylation or phosphonylating agents Vα, Vβ, Vγ or Vδ.
  L ² stands for a nucleophilically displaceable leaving group, such as halogen, for. B. chlorine or bromine, hetaryl, e.g. B. imidazolyl, carboxylate, e.g. B. acetate, or sulfonate, e.g. B. mesylate or triflate etc.
  The compounds of formula Vα, Vβ, Vγ or Vδ can be used directly, such as. B. in the case of carboxylic acid halides or generated in situ, for. B. activated carboxylic acids (with carboxylic acid and dicyclohexylcarbodiimide etc.).
• C) The preparation of compounds of formula I with R ⁴ = OR ¹¹ , SR ¹¹ , POR ¹³ R ¹⁴ , NR ¹⁵ R ¹⁶ , ONR ¹⁵ R ¹⁶ or N-linked heterocyclyl is carried out by reacting compounds of formula I with R ⁴ = Halogen, OSO ₂ R ¹² with compounds of the formula VIα, VIβ, VIγ, VIδ, VIε or VIη, optionally in the presence of a base or with prior salt formation.
  
• D) The preparation of compounds of the formula I with R ⁴ = SOR ¹² , SO ₂ R ¹² is carried out, for example, by reacting compounds of the formula I with R ⁴ = SR ¹² with an oxidizing agent.
  Examples of suitable oxidizing agents are m-chloroperbenzoic acid, peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen peroxide, optionally in the presence of a catalyst such as Wolf ramat.

The following conditions apply to the reactions mentioned under points B to E:
The starting compounds are generally used in an equimolar ratio. However, it can also be advantageous to use one or the other component in excess.

It may be advantageous to implement the In the presence of a base. The reactants and the base are expediently used in equimolar amounts.

With regard to procedures C and D it may be possible be advantageous, an excess of the base z. B. 1.5 to 3 mole equi to use valente based on the educt.

Suitable bases are tertiary alkylamines, such as triethylamine, aro Matic amines such as pyridine, alkali metal carbonates, e.g. B. sodium carbonate or potassium carbonate, alkali metal bicarbonates, such as  Sodium bicarbonate and potassium bicarbonate, alkali metal alcoholates such as sodium methoxide, sodium ethoxide, potassium tert butanolate or alkali metal hydrides, e.g. B. sodium hydride. Prefers triethylamine or pyridine are used.

As solvents such. B. chlorinated hydrocarbons, such as Methylene chloride or 1,2-dichloroethane, aromatic hydrocarbon fabrics, e.g. B. toluene, xylene or chlorobenzene, ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents such as acetonitrile, dimethyl form amide or dimethyl sulfoxide or esters, such as ethyl acetate, or mixtures thereof.

The reaction temperature is usually in the range from 0 ° C to to the level of the boiling point of the reaction mixture.

The workup can be carried out in a manner known per se towards the product respectively.

Depending on the reaction conditions, Ver drive B to D the compounds Ia, Ib or mixtures thereof be formed. The latter can be separated using classic separation methods, such as B. crystallization, chromatography, etc., are separated.

The cyclohexanediones from For mel III are known or can be made by methods known per se be produced (e.g. EP-A 71 707, EP-A 142 741, EP-A 243 313, US 4,249,937, WO 92/13821).

The alkylating agents Vα, sulfonylating agents Vβ, phosphonyly Vγ or Vδ, as well as the compounds VIα, VIβ, VIγ, VIδ and VIε are also known or can be after known processes are produced.

The carboxylic acids of the general formula IVa or their activated derivatives IVb can be analogous to known Establish process. The carboxylic acids IVa and their activated Derivatives IVb are new and also the subject of the present one Invention.

The carboxylic acids of the formula IVa with X = O (compounds of the formula IVa.O) are prepared by reacting the compounds of the compounds of the formula V, in which the radicals L can be the same or different and for a nucleophilically displaceable leaving group for mesylate, triflate or halogen, e.g. B. bromine, and the radicals R ² and R ^{3 have} the meanings given above, in an aqueous alkaline medium (see, for example, Kirmse et. Al. J. Am. Chem. Soc. 1986, 108, 6045-6046) :

Alkali metal hydroxides such as sodium hydroxide or are used as the base Potassium hydroxide, alkali metal carbonates such as sodium carbonate or Potassium carbonate or acetates such as sodium acetate.

The carboxylic acids of the formula IVa with X = S (compounds of the formula IVa.S) are prepared by reacting the compounds of the formula V, in which L can be the same or different and, for a nucleophilically displaceable leaving group such as mesylate, triflate or halogen, e.g. B. bromine, and the radicals R ² and R ^{3 have} the meanings given above, with hydrogen sulfide or its alkali metal or alkaline earth metal salts such as sodium sulfide or sodium hydrogen sulfide optionally in the presence of a base (see, for example, Lon-Tang et al J. Org. Chem, 1984, 49, 1027-1030; Kreher et al. Chem. Ber. 1991, 124, 645):

As a base z. B. alkali metal carbonates such as sodium carbo nate or potassium carbonate, alkali metal bicarbonates such as natri umhydrogencarbonate or tertiary amines such as. B. triethylamine or Pyridine.

The carboxylic acids of the formula IVa with X = S (O) _n (compounds of the formula IVa.SO) are prepared by reacting the compounds of the formula IVa.S with oxidizing agents:

Examples of suitable oxidizing agents are m-chloroperbenzoic acid acid, peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen pe roxid, optionally in the presence of a catalyst such as Wolfra mat, halogens, or oxygen, preferably in the presence of Photosensitizers. By choosing the oxidizing agent or Stoichiometry of the reagents used can be sulfoxides or Produce sulfones specifically (for the oxidation of thioethers to sul foxides and sulfones see also J. March, Advanced Organic Che mistry, 4th ed. Wiley 1992, p. 1201 ff and Litera cited there door).

The carboxylic acids of the formula IVa with X = NR ¹ (compounds of the formula IVa.N) are prepared by reacting the compounds of the formula V, in which the radicals R ¹ , R ² and R ^{3 have} the meanings mentioned above, with primary amines or primary amides, optionally in the presence of an auxiliary base or an excess of the amine (see, for example, US 4,652,573; Bornstein et al. Org. Synth. Col., Vol. V, 1973, 1064; Kreher et al. Chem. 1988, 112, 85-92):

Suitable auxiliary bases are, for example, alkali metal carbonates, such as sodium carbonate or potassium carbonate, tertiary amines such as. B. Triethylamine or pyridine, alkali metal hydrides such as. B. sodium hydride or potassium hydride or sterically demanding alcohols such as B. Potassium tert-butoxide.

The carboxylic acids of the formula IVa with X = N-NR ¹ R ¹⁷ (compounds of the formula IVa.NN) are prepared analogously to the preparation of compounds IVa.N by reacting the compounds of the formula V, in which the radicals R ¹ , R ² and R ^{3 has} the abovementioned meanings, with primary hydrazines or primary hydrazides, optionally in the presence of an auxiliary base or an excess of the hydrazine:

Compounds of the formula V can be prepared analogously to known processes. Compounds of the general formula V with L = halogen can be prepared starting from 2,3-dimethylbenzoic acids of the formula VI, in which R ² and R ^{3 have} the meanings mentioned above, for example by radical halogenation of the methyl groups in VI according to the following scheme:

Suitable halogenating agents are, for example, chlorine, bromine, N-chloramine, N-chlorosuccinimide, N-bromosuccinimide. Preferably the reaction takes place in the presence of a radical initiator. in the With regard to the radical starters come, among others, benzoyl pero xid or azobisisobutyronitrile. But it is also possible Lich, the reaction under radiation with suitable radiation sources such as UV-Hg low-pressure or Hg high-pressure lamps and / or perform with warming without an external radical starter perform. Process for halogenating compounds with Ortho-xylene structures are described in the literature (see e.g. Box et al., Heterocycles 1990, 31, 1261-1270; Röhrich et al., J. Org. Chem. 1992, 57, 2374; Hanack et al. Chem. Ber. 1992, 125; Hanack, ibid. 1243-1247).

The substituted 2,3-dimethylbenzoic acids of formula VI are in turn known (see e.g. EP-A 894 792; Merchant et al., J. At the. Chem. Soc. 1964, 2258-2261 - this document is hereby incorporated by reference  referred to in full) or can be analogous to those there described manufacturing process can be produced.

The examples given below serve to explain the Invention.

Manufacturing examples 1. Synthesis of the preliminary products 1.1 Synthesis of 7-sulfonylmethyl-1,3-dihydrobenzo [c] thiophene 4-carboxylic acid a) Bromine-2,3-dimethyl-4-thiomethylbenzene

592 g (3.69 mol) of bromine were added to a solution of 509 g (3.33 mol) of 2,3-dimethylthiophenol methyl ether in 3 l of glacial acetic acid at room temperature in the course of 3 h and the mixture was left to react for a further 3 h. The precipitated solid was suction filtered and discarded. 300 g of sodium acetate were added to the filtrate and the solvent was removed. The residue was taken up in dichloromethane and washed successively twice with sodium bicarbonate solution and once with brine. The organic phase was dried over sodium sulfate and then the solvent was removed. The title compound remained as a colorless solid.
Yield: 530 g (69%).
¹ H NMR (CDCl ₃ ) δ: 7.22 (d, 1H); 6.84 (d, 1H); 2.24 (s, 3H); 2.20 (s, 3H); 2.18 (s, 3H).

b) 2,3-dimethyl-4-thiomethylbenzoic acid

106 g (4.4 mol) of magnesium shavings in 100 ml of THF were etched with 1 ml of 1,2-dibromoethane and 11 g of bromoethane in 20 ml of THF. At 907 g (3.8 mol) of the product from stage a) in 1.5 l of THF were then added dropwise at room temperature over the course of 1 3/4 hours and then heated under reflux for a further hour. Then you passed in at -10 ° C 1750 g of carbon dioxide as a gas and stirred the suspension obtained overnight at room temperature. The mixture thus obtained was stirred in a mixture of 2.3 l of water, 800 ml of conc. Hydrochloric acid and 1 kg of ice and sucked off the resulting precipitate. It was washed twice with 1 liter of petroleum ether and the solid thus obtained was dried in vacuo.
Yield: 647 g (87%).
Mp: 210 ° C

c) 2,3-Dimethyl-4-sulfonylmethylbenzoic acid

136 g (1.2 mol) of hydrogen peroxide (30%) were added dropwise to a suspension of 65 g (330 mmol) of the product from stage b) and 10 g (30 mmol) of sodium tungstate dihydrate in 550 ml of glacial acetic acid and the mixture was stirred overnight . 500 ml of water were added and the precipitate formed was filtered off with suction.
Yield: 67 g (88%).
Mp: 220 ° C

d) 2,3-bis (bromomethyl) -4-sulfonylmethylbenzoic acid

To a mixture of 57 g (250 mmol) of the product from step c), 2 g of conc. Sulfuric acid, 208 g (1.2 mol) of hydrobromic acid (47%) and 600 ml of chlorobenzene were added at 70 ° C in portions to 190 g (560 mmol) of hydrogen peroxide (10%) and stirring was continued for 1 h. The mixture was allowed to cool and the precipitate formed was filtered off with suction. The residue was then digested with petroleum ether and dried. The title compound was thus obtained in a yield of 79 g (82%).
Mp: 167 ° C

e) 7-sulfonylmethyl-1,3-dihydrobenzo [c] thiophene-4-carboxylic acid (Pre-stage 1)

80 mg (2.1 mmol) of sodium hydroxide and 0.4 g were added to a solution of 0.8 g (2.1 mmol) of the product from stage d) in 30 ml of ethanol, 15 ml of THF and 1.5 ml of water (5.1 mmol) sodium sulfide (60-62%). After 2 hours at reflux, the solvent was removed, the residue was taken up in water and acidified with hydrochloric acid. The title compound precipitated as a solid, which was filtered off and dried.
Yield: 0.4 g (74%).
Mp: 280-282 ° C

1.2 Synthesis of 7-sulfonylmethyl-1,3-dihydrobenzo [c] furan-4- carboxylic acid (precursor 2)

A mixture of 182 g (472 mmol) of the product from stage 1.1 d), 38 g of sodium acetate and 2.8 l of water was heated to 90 ° C. for 5 h. The mixture was filtered hot and the filtrate was left to stand at room temperature overnight. The title compound crystallized out as a solid, which was filtered off and dried.
Yield: 60 g (53%).
Mp: 245-250 ° C

2. Synthesis of the end products 2.1 2 - {(7-sulfonylmethyl-1,3-dihydrobenzo [c] furan-4-yl) - carbonyl} -1-hydroxy-cyclohex-1-en-3-one (Example 1)

2.0 g (8.3 mmol) of precursor 2, dissolved in 30 ml of acetonitrile, were mixed with 0.9 g (8.3 mmol) of cyclohexane-1,3-dione and 1.7 g (8.3 mmol) N, N-dicyclohexylcarbodiimide were added and the mixture was stirred at room temperature for 3 h. Then 1.7 g (16.5 mmol) of triethylamine and 0.4 ml of trimethylsilyl cyanide were added and the mixture was stirred for a further 4 h at room temperature. 50 ml of 2% sodium carbonate solution and ethyl acetate were added and the precipitate was filtered off with suction. The alkaline aqueous phase was extracted once with ether and adjusted to pH 4 with hydrochloric acid. The title compound crystallized out.
Yield: 1.4 g (50%).
Mp: 155-156 ° C

b) Synthesis of 2 - {(7-sulfonylmethyl-1,3-dihydrobenzo [c] furan 4-yl) -carbonyl} -1-chlorocyclohex-1-en-3-one (Example 2)

0.68 g (5.4 mmol) of oxalyl chloride was added dropwise to a solution of 0.9 g (2.7 mmol) of the compound from example 1 in 20 ml of dichloromethane and 3 drops of dimethylformamide, and the mixture was then refluxed for 2 h heated. The mixture was poured into water, the organic phase was dried over sodium sulfate and the solvent was removed. The title compound was obtained as a yellow solid.
Yield: 0.9 g (94%).
Mp: 172-174 ° C

2.3 2 - {(7-sulfonylmethyl-1,3-dihydrobenzo [c] furan-4-yl) - carbonyl} -1- (N-methoxy-N-methyl) aminocyclohex-1-en-3-one (Example 3)

82 mg (0.85 mmol) of N, O-dimethylhydroxylamine hydrochloride in 10 ml of dimethyl sulfoxide were mixed with 140 mg (1.69 mmol) of sodium hydrogen carbonate. Then 300 mg (0.85 mmol) of the compound from Example 2 were added in portions and the mixture was stirred for a further 2 h. The mixture was poured into water and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. The residue was chromatographed on silica gel with cyclohexane and ethyl acetate (2: 3) as the eluent. After concentration of the eluate, the title compound was obtained as a colorless solid.
Yield: 0.1 g (31%).
¹ H NMR (CDCl ₃ ) δ: 7.85 (d, 1H); 7.78 (d. 1H); 5.50 (s, 2H); 5.40 (s, 2H); 3.28 (s. 3H); 3.18 (s, 3H); 3.02 (s, 3H); 2.50 (t, 2H); 2.42 (t, 2H); 2.12 (m, 2H).

2.4 2 - {(7-Sulfonylmethyl-1,3-dihydrobenzo [c] thiophene-4-yl) carbo nyl} -1-hydroxy-cyclohex-1-en-3-one (Example 4)

A mixture of 0.7 g (2.7 mmol) of precursor 1, 0.3 g (2.7 mmol) of 1,3-cyclohexanedione, 0.56 g (2.7 mmol) of N, N-dicyclohexyl carbodiimide and 30 ml of acetonitrile was stirred at room temperature overnight. Then 0.55 g (5.4 mmol) of triethylamine and 0.05 ml of trimethylsilyl cyanide were added and the mixture was stirred for a further 4 h. It was added to 50 ml of 2% sodium carbonate solution and ethyl acetate and the precipitate was suction filtered. The aqueous phase was washed once with ether and adjusted to pH 4 with hydrochloric acid. The precipitate formed was suction filtered and dried. Chromatography on silica gel provided the product.
Yield: 170 mg (18%).
Mp: 177-179 ° C

In addition to the compounds of Examples 1, 2, 3 and 4 described above, Table 1 below lists further cyclohexenone derivatives of the formula I which were prepared in an analogous manner from precursor 1 and precursor 2.

The compounds of formula I and their agricultural usable salts are suitable both as isomer mixtures and also in the form of pure isomers - as herbicides. The herbicidal Agents containing compounds of the formula I control plants Zen growth very good on non-cultivated areas, especially in high areas Application rates. In crops such as wheat, rice, corn, soy and tree they work against weeds and grass weeds without the cult significant damage to door plants. This effect occurs before al lem at low application rates.

Depending on the particular application method, the compounds of the formula I or herbicidal compositions comprising 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, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. 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, Coffea libericaus), Cucumodison , Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoealumisisumisum , Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium , Prunus persica, Pyrus communis, Ribes sylvestre, Rieinus communis, Saecharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (see vulgare), Theobroma cacao, Trifolium praten se, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds Ia and Ib can also be cultivated through breeding including genetic engineering methods are tolerant to the action of herbicides.

The application of the herbicidal compositions or the active compounds can be carried out in Pre-emergence or post-emergence. Are the real substances less tolerable for certain crops, so can Spreading techniques are applied in which the herbizi the agents are sprayed with the help of sprayers so that  the leaves of sensitive crops if possible not to be taken while the active ingredients are on the leaves including growing unwanted plants or the uncovered Floor space (post-directed, lay-by).

The compounds Ia or Ib or the herbicides containing them Agents can for example be in the form of directly sprayable aqueous solutions, powders, suspensions, including high-proof aqueous, oily or other suspensions or dispersions, Emulsions, oil dispersions, pastes, dusts, spreading agents or granules by spraying, atomizing, dusting, ver sprinkle or pour. The application forms rich depending on the purposes; they should in any case the finest possible distribution of the active compounds according to the invention guarantee.

The following essentially come into consideration as inert additives: mine Potassium oil fractions from medium to high boiling point, such as kerosene or diesel oil, as well as coal tar oils and vegetable or of animal origin, aliphatic, cyclic and aromatic Hydrocarbons, e.g. B. paraffin, tetrahydronaphthalene, alky gated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, buta nol, cyclohexanol, ketones such as cyclohexanone or strongly polar solvents means, e.g. B. amines such as N-methylpyrrolidone or water.

Aqueous use forms can be obtained from emulsion concentrates, Sus pensions, pastes, wettable powders or water-dispersible Granules can be prepared by adding water. For the manufacture emulsions, pastes or oil dispersions, the sub substituted ureas as such or in an oil or solution medium solution, by means of wetting, adhesive, dispersing or emulsifying agents medium homogenized in water. But it can also come from active substance, wetting, adhesive, dispersing or emulsifying agent and possibly concentrates containing solvents or oil are provided, which are suitable for dilution with water.

The alkali, alkaline earth, Am monium salts of aromatic sulfonic acids, e.g. B. lignin, phenol, Naphthalene and dibutylnaphthalenesulfonic acid, as well as from fatty acid ren, alkyl and alkylarylsulfonates, alkyl, lauryl ether and Fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and Octadecanols as well as fatty alcohol glycol ether, condensation pro products of sulfonated naphthalene and its derivatives with formal dehyde, condensation products of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde, polyoxyethylene octylphe nol ether, ethoxylated isooctyl, octyl or nonylphenol, Al  kylphenyl, tributylphenyl polyglycol ether, alkylaryl polyetheral alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxy propylene alkyl ether, lauryl alcohol polyglycol ether acetate, sorbitol ster, lignin sulfite or methyl cellulose.

Powders, materials for spreading and dusts can be mixed or mixed joint grinding of the active substances with a solid Carrier are manufactured.

Granules, e.g. B. coating, impregnation and homogeneous granules can Herge by binding the active ingredients to solid carriers be put. Solid carriers are mineral soils like pebbles acids, silica gels, silicates, talc, kaolin, limestone, lime, Chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and ma magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as flour, tree bark, wood and Nutshell flour, cellulose powder or other solid carriers.

The concentrations of the active ingredients Ia and Ib in the application Finished preparations can be varied in a wide range the. The formulations generally contain 0.001 to 98% by weight, preferably 0.01 to 95 wt .-%, at least one active fabric. The active ingredients are in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum) is used.

The compounds Ia or Ib according to the invention can, for example, be formulated as follows:

• 1. I 20 parts by weight of compound no. 4 are in a Mi solved, which from 80 parts by weight of alkylated Ben zol, 10 parts by weight of the adduct from 8 to 10 moles of ethylene oxide to 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 out and finely distributing the solution in 100,000 parts by weight Water gives an aqueous dispersion that Contains 0.02% by weight of the active ingredient.
• 2. II 20 parts by weight of compound no. 1 are in a Mi solution, which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the app tion product of 7 moles of ethylene oxide to 1 mole of isooctyl phenol and 10 parts by weight of the adduct of There are 40 moles of ethylene oxide with 1 mole of castor oil. By one  pour and finely distribute the solution in 100,000 Ge most parts of water, an aqueous dispersion is obtained, which contains 0.02% by weight of the active ingredient.
• 3. IV 20 parts by weight of active ingredient no. 4 are mixed with 3 Ge most of the sodium salt of diisobutylnaphthalene sulfonic acid, 17 parts by weight of the sodium salt one Lignin sulfonic acid from a sulfite waste liquor and 60 Ge most parts of powdered silica gel mixed well and ground in a hammer mill. Through fine distribution len the mixture in 20,000 parts by weight of water a spray mixture containing 0.1% by weight of the active ingredient holds.
• 4. V 3 parts by weight of active ingredient no. 4 are mixed with 97 Ge most parts of finely divided kaolin mixed. You get in this way a dusting agent containing 3% by weight of the active ingredient contains.
• 5. VI 20 parts by weight of active ingredient no. 4 are mixed with 2 Ge important parts of calcium salt of dodecylbenzenesulfonic acid, 8 Parts by weight of fatty alcohol polyglycol ether, 2 parts by weight share sodium salt of a phenol-urea-formaldehyde Condesates and 68 parts by weight of a paraffinic Mi mineral oil intimately mixed. A stable oily is obtained Dispersion.
• 6. VII 1 part by weight of compound no. 1 is in a Mi dissolved in 70 parts by weight of cyclohexanone, 20 Parts by weight of ethoxylated isooctylphenol and 10 Ge major parts of ethoxylated castor oil. You get a stable emulsion concentrate.
• 7. VIII 1 part by weight of compound no. 1 is in a Mi solved, consisting of 80 parts by weight of cyclohexanone and 20 parts by weight Wettol® EM 31 (non-ionic emul gator based on ethoxylated castor oil). Man he holds a stable emulsion concentrate.

To broaden the spectrum of activity and to achieve synergistic effects, the substituted ureas Ia or Ib 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-1,3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF ₃ -phenyl derivatives, carbamates, quinolinecarboxylic acid and their derivatives, chloroacetanilides, cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid and their derivatives, Dihydro benzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxadiazoles, oxadiazoles, oxadiazoles, oxadiazoles, oxadiazoles, oxadiazoles, oxirazoles, , Phenols, aryloxy or heteroaryloxyphenoxypropionic acid esters, phenylacetic acid and its derivatives, phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acids and their derivatives, pyrimidyl ethers, Sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides, uraciles into consideration.

It may also be useful to use the compounds Ia or Ib al alone or in combination with other herbicides mixed with other crop protection products to apply together, for example with pest control agents or phytopathogenic fungi or bacteria. It is also of interest the miscibility with mineral salt solutions, which are used to eliminate Nutritional and trace element deficiencies are used. It can non-phytotoxic oils and oil concentrates can also be added. Depending on the target, the amount of active ingredient applied is Season, target plants and stage of growth 0.001 to 3 preferably 0.01 to 1.0 kg / ha of active substance (see p.).

part B Examples of use

The herbicidal activity of the substituted ureas of the formula Ia or Ib was demonstrated by greenhouse tests:
Plastic 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 or suspended in water emulsified active ingredients directly after sowing by means of a fine distribution lender nozzles applied. The vessels were irrigated slightly To promote germination and growth, and then with covered plastic hoods until the plants had grown This cover causes the test to germinate evenly  plant, unless this is affected by the active ingredients has been.

For the purpose of post-emergence treatment, the test plants were each depending on the growth form only up to a height of 3 to 15 cm pulled and then with those suspended or emulsified in water Active substances treated. The test plants were either di sown right and grown in the same containers or they were only grown separately as seedlings and a few days before Treatment transplanted into the test vessels. The application rate for post-emergence treatment was 0.5, 0.25 and 0.125 kg / ha active Substance.

The plants became species-specific at temperatures from 10 to 25 ° C or 20 to 35 ° C kept. The trial period extended yourself over 2 to 4 weeks. During this time, the plants 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 above-ground parts and 0 no damage or normal waking course of life.

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

Table 1

Herbicidal activity in post-emergence applications in greenhouses (example compound no. 4)

Table 2

Herbicidal activity in post-emergence applications in greenhouses (example compound no. 10)

Table 3

Herbicidal activity in post-emergence applications in greenhouses (Example No. 1)

Claims (11)

1. cyclohexenone derivatives of bicyclic benzoic acids of the general formula I,
wherein
X represents O, S, SO, SO ₂ , NR ¹ or N-NR ¹ R ¹⁷ ,
R ^{1 is} hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ - Haloalkylsulfonyl, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ haloalkylcarbonyl, C ₁ -C ₆ alkylcarbonyl-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylcarbonyl-C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkylcarbonyloxy-C ₁ -C ₆ alkyl,
C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkoxy, C ₃ -C ₆ cycloalkylcarbonyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkoxy-C ₁ -C ₆ -alkyl, C ₃ -C ₆ -cycloalkylcarbonyl-C ₁ -C ₆ -alkyl, C ₃ -C ₆ -cycloalkoxycarbonyl-C ₁ -C ₆ -alkyl, C ₃ -C ₆ -cycloalkylcarbonyloxy-C ₁ -C _6- alkyl, C ₃ -C ₆ -cycloalkylsulfonyl,
Phenyl, phenylsulfonyl, phenylcarbonyl, phenyl-C ₁ -C ₆ -alkyl, phenyl-C ₁ -C ₆ -alkylcarbonyl, phenoxy-C ₁ -C ₆ -alkyl, phenylcarbonyl-C ₁ -C ₆ -alkyl, phenoxycarbonyl-C ₁ Is -C ₆ alkyl, or phenylcarbonyloxy-C ₁ -C ₆ alkyl,
Are heterocyclyl, heterocyclylsulfonyl, heterocyclylcarbonyl, heterocyclyl-C ₁ -C ₆ -alkyl, heterocyclylcarbonyl-C ₁ -C ₆ -alkyl or heterocyclylcarbonyloxy-C ₁ -C ₆ -alkyl,
where the phenyl, heterocyclyl and cycloalkyl radicals of the abovementioned groups are optionally one, two, three or four substituents selected from C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ - C ₄ haloalkoxy, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ haloalkylcarbonyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, nitro, hydroxy or cyano and / or partially or completely halogenated could be;
R ² halogen, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl or C ₁ -C ₆ - Haloalkylsulfonyl;
R ^{3 represents} hydrogen, halogen, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl, and
Hex for substituted (3-oxo-1-cyclohexen-2-yl) carbonyl of the formula IIa or for substituted (1,3-dioxo-2-cyclohexyl) methylidene of the formula IIb
stand, whereby the variables R ⁴ to R ^{10 have the} following meaning:
R ⁴ hydroxy, mercapto, halogen, OR ¹¹ , SR ¹¹ , SOR ¹² , SO ₂ R ¹² , OSO ₂ R ¹² , P (O) R ¹³ R ¹⁴ , OP (O) R ¹³ R ¹⁴ , P (S) R ¹³ R ¹⁴ , OP (S) R ¹³ R ¹⁴ , NR ¹⁵ R ¹⁶ , ONR ¹⁵ R ¹⁶ or N-linked heterocyclyl, which can be partially or completely halogenated and / or can carry one, two or three of the following radicals: Nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy;
R ⁵ , R ⁹ independently of one another are hydrogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxycarbonyl;
R ⁶ , R ⁸ , R ¹⁰ independently of one another are hydrogen or C ₁ -C ₄ alkyl;
R ^{7 is} hydrogen, halogen, hydroxy, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, di- (C ₁ -C ₆ alkoxy) methyl, (C ₁ -C ₆ alkoxy) - (C ₁ -C ₆ alkylthio) methyl, di (C ₁ -C ₆ alkylthio) methyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ - C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ -Haloalkoxycarbonyl;
1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3 oxathian-2-yl, 1,3-dithiolan-2-yl or 1 , 3-dithian-2-yl, where the six latter radicals can be substituted by one to three C ₁ -C ₄ alkyl radicals; or
R ⁶ and R ⁸ or R ⁸ and R ¹⁰ together form an n bond or a C ₁ -C ₅ alkyl chain which can carry one or two radicals from the following group: halogen, cyano, C ₁ -C ₄ alkyl , C ₁ -C ₄ haloalkyl or C ₁ -C ₄ alkoxy carbonyl; or
R ⁶ and R ¹⁰ together form a C ₁ -C ₄ alkyl chain which can carry one or two radicals from the following group: halogen, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ alkoxycarbonyl; or
R ⁷ and R ⁸ together form an -O- (CH ₂ ) _p -O-, -O- (CH ₂ ) _p -S-, -S- (CH ₂ ) _p -S-, -O- (CH ₂ ) _q - or -S- (CH ₂ ) _q chain, in which p are 2, 3, 4 or 5 and q are 2, 3, 4, 5 or 6, and which consists of one, two or three radicals the following group can be substituted: halogen, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ alkoxycarbonyl; or
R ⁷ and R ⁸ together with the carbon to which they are attached form a carbonyl group;
and in which the variables R ¹¹ to R ^{17 have} the following meanings:
R ^{11 is} C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₆ haloalkynyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkylcarbonyl, C ₂ -C ₆ alkenylcarbonyl, C ₂ -C ₆ alkynylcarbonyl, C ₃ -C ₆ cycloalkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, C ₃ -C ₆ alkenyloxycarbonyl, C ₃ -C ₆ -alkynyloxycarbonyl, C ₁ -C ₆ -alkylthiocarbonyl, C ₁ -C ₆ -alkylaminocarbonyl, C ₃ -C ₆ -alkenylaminocarbonyl, C ₃ -C ₆ -alkynylaminocarbonyl, N, N-Di (C ₁ -C ₆ - alkyl) aminocarbonyl, N- (C ₃ -C ₆ alkenyl) -N- (C ₁ -C ₆ alkyl) aminocarbonyl, N- (C ₃ -C ₆ alkynyl) -N- (C ₁ -C ₆ -alkyl) -aminocarbonyl, N- (C ₁ -C ₆ -alkoxy) -N- (C ₁ -C ₆ -alkyl) -aminocarbonyl, N- (C ₃ -C ₆ -alkenyl) -N- (C ₁ - C ₆ -alkoxy) -aminocarbonyl, N- (C ₃ -C ₆ -alkynyl) -N- (C ₁ -C ₆ -alkoxy) -aminocarbonyl, di- (C ₁ -C ₆ -alkyl) -aminothiocarbonyl, C ₁ -C ₆ -alkoxyimino-C ₁ -C ₆ alkyl, where the alkyl, cycloalkyl or alkoxy radicals mentioned can be partially or completely halogenated and / or one, two or three of the fo Lying groups can carry: cyano, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, di (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ - Alkoxycarbonyl, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkoxycarbonyl, hydroxycarbonyl, C ₁ -C ₄ alkylaminocarbonyl, di- (C ₁ -C ₄ alkyl) aminocarbonyl, aminocarbonyl, C ₁ -C ₄ alkylcarbonyloxy or C ₃ -C ₆ cycloalkyl,
Phenyl, phenyl-C ₁ -C ₆ -alkyl, phenylcarbonyl-C ₁ -C ₆ -alkyl, phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl, phenylaminocarbonyl, N- (C ₁ -C ₆ -alkyl) -N-phenylaminocarbonyl, phenyl-C ₂ -C ₆ -alkenylcarbonyl, heterocyclyl, heterocyclyl-C ₁ -C ₆ -alkyl, heterocyclylcarbonyl-C ₁ -C ₆ -alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylaminocarbonyl, N- (C ₁ -C ₆ -Al- heterocyclylaminocarbonyl or heterocyclyl-C ₁ -C ₆ -alkenylcarbonyl, where the phenyl or heterocyclyl radical of the 18 latter substituents can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C ₁ - C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy;
R ^{12 is} C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl or C ₃ -C ₆ cycloalkyl, where the four radicals mentioned can be partially or completely halogenated and / or one , can carry two or three of the following groups: cyano, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ Alkylcarbonyl, C ₁ -C ₄ alkoxycarbonyl or C ₁ -C ₄ haloalkoxycarbonyl,
Phenyl, phenyl-C ₁ -C ₄ -alkyl, heterocyclyl or heterocyclic-C ₁ -C ₄ -alkyl, where the phenyl or the heterocyclic radical of the four last-mentioned substituents can be partially or completely halogenated and / or one, two or can carry three of the following radicals: nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ alkoxycarbonyl ;
R ¹³ , R ¹⁴ independently of one another are hydrogen, hydroxyl, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylthio, phenyl, phenyl-C ₁ -C ₄ -alkyl or phenoxy, where the three last-mentioned substituents can be partially or completely halogenated and / or can carry one, two or three of the following radicals: nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ Alkoxy, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ alkoxycarbonyl;
R ^{15 is} hydrogen, C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₆ haloalkynyl, C ₃ -C ₆ - Cycloalkyl, C ₁ -C ₆ alkylcarbonyl, hydroxy, C ₁ -C ₆ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkynyloxy, amino, C ₁ -C ₆ alkylamino, di- (C ₁ -C ₆ alkyl) amino or C ₁ -C ₆ alkylcarbonylamino, where the alkyl, cycloalkyl or alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one, two or three of the following radicals: cyano, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkylaminocarbonyl, di- (C ₁ -C ₄ alkyl) aminocarbonyl or C ₃ -C ₆ cycloalkyl,
Phenyl, phenyl-C ₁ -C ₄ -alkyl, phenylcarbonyl, heterocyclyl, heterocycly-C ₁ -C ₄ -alkyl or heterocyclylcarbonyl, where the phenyl or heterocyclyl radical of the six last-mentioned substituents can be partially or completely halogenated and / or one can carry up to three of the following radicals: nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy;
R ¹⁶ , R ¹⁷ independently of one another are hydrogen, C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl;
and their agriculturally useful salts. 2. Cyclohexenone derivatives according to claim 1, wherein R ² in formula I is halogen, C ₁ -C ₄ alkylsulfonyl or C ₁ -C ₄ haloalkylsulfonyl. 3. Cyclohexenone derivatives according to one of the preceding claims, wherein X in formula I is NR ¹ , wherein
R ^{1 is} C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ alkyl sulfonyl, phenyl, phenyl-C ₁ -C ₄ alkyl or phenylsulfonyl, where the phenyl ring of the last three groups can be substituted in the 4-position with halogen or C ₁ -C ₄ alkyl. 4. Cyclohexenone derivatives according to one of claims 1 to 3, wherein X in formula I is N-NR ¹ R ¹⁷ , wherein
R ^{1 is} C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ alkyl sulfonyl, phenyl, phenyl-C ₁ -C ₄ alkyl or phenylsulfonyl, where the phenyl ring of the latter three groups in the 4-position can be substituted by halogen or C ₁ -C ₄ alkyl, and
R ^{17 is} hydrogen or C ₁ -C ₄ alkyl. 5. cyclohexenone derivatives according to any one of the preceding claims, wherein hex in formula I represents a radical of formula IIa, wherein R ^{4 is} selected from hydroxy, mercapto, halogen, OR ¹¹ , SR ¹¹ , SO ₂ R ¹² , OSO ₂ R ¹² , NR ¹⁵ R ¹⁶ and optionally substituted, N-linked heterocyclyl with the meanings given for R ¹¹ , R ¹² , R ¹⁵ and R ¹⁶ in claim 1. 6. Cyclohexenone derivatives according to claim 5, wherein in formula I hex represents a radical IIa and
R ^{4 is} selected from hydroxy, C ₁ -C ₄ alkylcarbonyloxy, C ₁ -C ₄ alkylamino, di-C ₁ -C ₄ alkylamino, C ₁ -C ₄ alkylthio, N- (C ₁ -C _4- alkyloxy) -N- (C ₁ -C ₄ -alkyl) amino, C ₁ -C ₄ -alkylsulfonyloxy, phenylthio, phenylsulfonyl, phenylsulfonyloxy and N-linked heterocyclyl, the phenyl group and the heterocyclyl group having the four last-mentioned substituents Halogen, nitro, cyano or C ₁ -C ₄ alkyl may be substituted. 7. Cyclohexenone derivatives according to one of the preceding claims, wherein in formula IIa or IIb
R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ independently of one another represent hydrogen or C ₁ -C ₄ alkyl,
R ^{7 can} also represent hydroxy, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, halo genalkoxy or haloalkylthio, or
R ⁷ and R ⁸ together with the carbon atom to which they are bound are also a carbonyl group, a 1,3-dioxolane, 1,3-dithiolane, 1,3-oxothiolane, 1,3-oxothiane , 1,3-dithiolane or a 1,3-dithiane ring, where the 2-position of the six rings mentioned is identical to the carbon atom to which R ¹¹ and R ^{12 are} bound,
R ⁵ and R ⁹ or R ⁶ and R ^{10 can} also mean a C ₁ -C ₄ alkylene chain, or
R ⁶ and R ⁸ or R ⁸ and R ⁹ together can form an n bond. 8. Bicyclic benzoic acids of the general formula IVa
wherein X, R ² and R ^{3 have} the meanings given in claim 1. 9. Agent containing at least one cyclohexenone derivative Formula I or an agriculturally useful salt of I. according to one of claims 1 to 7, and conventional auxiliaries. 10. a method for controlling undesirable plant growth, characterized in that a herbicidally effective amount at least one cyclohexenone derivative of the formula I or  of an agriculturally useful salt of I according to one of claims 1 to 7, on plants, their habitat and / or can act on seeds. 11. Use of cyclohexenone derivatives of the formula I or their agriculturally useful salts according to one of the claims che 1 to 7 as herbicides.