MXPA00012738A

MXPA00012738A - 2,4-diamino-1,3,5-triazine, method for the production and use of the same as herbicides and plant growth regulators

Info

Publication number: MXPA00012738A
Application number: MXPA/A/2000/012738A
Authority: MX
Inventors: Lothar Willms; Thomas Auler; Christopher Rosinger; Hermann Bieringer; Klemens Minn; Wolfgang Giencke
Original assignee: Aventis Cropscience Gmbh
Priority date: 1998-06-16
Filing date: 2000-12-18
Publication date: 2002-07-25

Abstract

The invention relates to compounds having formula (I), wherein R1, R2, R3, R4, A1, A2, X and n have the meanings defined in Claim 1. Said compounds and the salts thereof are suitable as herbicides and plant growth regulators. Said compounds (I) can be produced according to the method disclosed in Claim 7, in part, by means of novel intermediate products, e.g. of formula (III) and (V).

Description

2. 4-DIAMINO-1.3.5-TRIAZ1NAS, ITS PREPARATION. AND USE AS HERBICIDES AND AS REGULATORS OF GROWTH OF PLANTS DESCRIPTIVE MEMORY The invention is in the technical field of crop protection agents such as herbicides and plant growth regulators, in particular of herbicides for the selective control of harmful plants in crops of useful plants. It is known that 2-amino-4- (N-phenylalkylamino) -1, 3,5-triazines which are substituted in position 6 and which can be substituted additionally having herbicidal properties and plant growth regulators; cf. WO 97/08156 and in the literature cited therein, and WO 98/15537 and the literature cited therein; see also the aspects of WO 97/00254 and the literature cited therein. When known active substances are used, some of them have disadvantages, be insufficient herbicidal action against harmful plants, a very narrow harmful plants spectrum which can be controlled by an active substance, or too little capacity selection in plant crops tools. Other active substances can not be produced economically on an industrial scale because their precursors and reagents are difficult to obtain, or because their chemical stability properties are insufficient. ii iii fi í li l Iî Itillitff * "- -" • ' "- - - - • - - •' • - - '• * i- -» - > -'.... - - - " . *. * a ^ »» .. ^.

An object of the invention is to provide alternative active substances of the type of 2,4-diamino-1, 3,5-triazines, which, if appropriate, can conveniently be used as herbicides or as regulators of plant growth. The present invention relates to compounds of the formula (I) and salts thereof wherein R1 is aryl that is substituted or unsubstituted and, including substituents, preferably has from 6 to 30 carbon atoms, or is (C3-C9) cycloalkyl, which is substituted or unsubstituted and which, including substituents, preferably has from 3 to 30 carbon atoms, or is heterocyclyl which is substituted or unsubstituted and which, including substituents, preferably has from 2 to 30 carbon atoms, or alkyl (C -? - C6) , (C2-C2) alkenyl or (C2-C6) alkynyl, each of the last three mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, nitro, thiocyanate, alkoxy (C1-C4), halogenoalkoxy (C2-C4), alkenyloxy (C2-C), halogenoalkenyloxy (C2-C4), alkylthio (CrC4), alkylsulfinyl (C1-C4), alkylsulfonyl (C? -C4), *. * * * * ** +. ^ -. - .. . . »,.,» > . . . . Y " . ".." halogenalkylsulfinyl (CrC4), halogenoalkylsulfonyl (C1-C4) and cycloalkyl (C3-Cg) which is unsubstituted or substituted, and phenyl which is unsubstituted or substituted and heterocyclyl which is unsubstituted or substituted, and the formulas R'-C (= Z ') -, R'-C (= Z') - Z-, R, -ZC (= Z ') -, R, R "NC (= Z') -, R '-ZC (= Z') - O-, R'R "NC (= Z ') - Z-, R'-ZC (= Z') - NR" - and R, R "NC (= Z ') -NR '"- in which R \ R" and R' "in each case independently of one another are alkyl (C Cß), aryl, aryl- (C? -C6) alkyl, (C3-Cg) cycloalkyl or cycloalkyl (C3-C9) -alkyl (C? -C6), each of the last 5 mentioned radicals being substituted or unsubstituted, and wherein Z and Z 'independently of each other are in each case an oxygen or sulfur atom , and in which, including the substituents, preferably has from 1 to 30 carbon atoms, R2 is (C3-Cg) cycloalkyl which is unsubstituted or substituted, (C4-C9) cycloalkenyl which is unsubstituted or substituted, heterocyclyl which is unsubstituted or substituted, or phenyl, which is unsubstituted or substituted, R2, including substituents, preferably has up to 30 carbon atoms, or R3 is hydrogen, alkyl (Ci-Cß), aryl or cycloalkyl (C3-C9), each one of the last 3 radicals mentioned being replaced or not • substituted, or a radical of the formula -N (B1-D1) (B2-D2) or -NR'-N (B1-D1) (B2-D2) in which B1, B2, D1 and D2 are in each as defined below and R -hydrogen, alkyl (CrC6) or [(C? -C6) alkyl] carbonyl, R3 including substituents, preferably having up to 20 carbon atoms, R4 is a radical of the formula -B-D3, B3 and D3 being as defined below and R4, including substituents, preferably having up to 20 carbon atoms, A1 is straight-chain alkylene having from 1 to 5 atoms of straight-chain carbon or alkenylene or alkynylene, each of which has from 2 to 5 carbon atoms, each of the last three divalent radicals mentioned being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, cyano, thiocyanate and radicals of the formula B4-D4, B4 and D4 as defined below, A2 is a straight-chain or straight-chain alkylene having 1 to 4 carbon atoms or alkenylene or alkynylene, straight chain, each of which has from 2 to 5 carbon atoms, each of the last three mentioned divalent radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of palógeno, nitr or, cyano, thiocyanate and radicals of the formula -EJ5-D5 or a divalent radical of the formula V1, V2, V3, V4, or V5, -CR6R7-W * -CR8R9- (V1) -CR10R11-W * -CR12R13 -CR14R15- (V2) -CR16R 7-CR18R19-W * -CR20R21- (V3) -CR22R23-CR24R25-W * - (V4) -CR26R27-W * - (V5) each of the radicals R6 or R27 in each case independently of one another is hydrogen, halogen, nitro, cyano, thiocyanate or a radical of the formula -B6-D6, W * is in each case an oxygen atom, an atom of sulfur or a group of the formula N (B7-D7) and B5, B6, B7, D5 D6 and D7 are as defined below, B1, B2, B3 and B7 in each case independently of one another are a direct or divalent linking group of the formulas -C (= Z *) -, -C (= Z) *) - Z ** -, -C (= Z *) - NH- or -C (= Z *) - NR * -, Z * being an oxygen or sulfur atom, Z ** an oxygen or sulfur atom and R * alkyl (Ci-Cß), aryl, aryl- (CrC6) alkyl, (C3-Cg) cycloalkyl or (C3-C9) -alkyl (CrC6) cycloalkyl, each of the last 5 mentioned radicals are unsubstituted or substituted e, including substituents, preferably have up to 20 carbon atoms, B4, B5 and B6 in each case independently of one another are a direct linking group or a divalent group of the formulas -O-, -S (O ) p-, - 15 S (O) pO-, -OS (O) p-, -CO-, -O-CO-, -CO-O-, S-CO-, -CO-S-, -S -CS-, -CS-S-, - O-CO-O-, -NR ° -, -O-NR0-, NR ° -O-, - NR ° -CO-, -CO-NR0-, -O -CO-NR ° - or - NR ° -CO-O-, p being the integer 0, 1, or 2 and R ° being hydrogen, alkyl (Ci-Cß), aryl, aryl- (C? -C6) alkyl, cic (C3-C8) alkyl or (C3-C9) cycloalkyl (C6C6) alkyl, each of the last mentioned radicals are unsubstituted or substituted and including substituents, preferably having up to 20 carbon atoms, D1, D2, D3, D4, D5 and D6 in each case independently of one another are hydrogen, alkyl (C Cβ), aryl, aryl- (CrC6) alkyl, cycloalkyl (C3-) ^. ^ > A > ^ C9) or (C3-Cg) cycloalkyl-alkyl (CrC6), each of the last 5 radicals mentioned are unsubstituted or substituted and, including substituents, preferably have up to 20 carbon atoms, or in each case two radicals D5 of two groups -B5-D5 that are attached to a carbon atom are bonded together and form an alkylene group having from 2 to 4 carbon atoms, this alkylene group is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4) alkyl ) and (C 1 -C 4) alkoxy, (X) n is n X substituents, where the X in each case independently of one another are halogen, hydroxyl, amino, nitro, formyl, carboxyl, cyano, thiocyanate, aminocarbonyl, or alkyl (Ci-Cß), alkoxy (Ci-Cß), alkylthio (CrCß), monoalkylamino (Ci-Cß) , (C 1 -C 4) dialkylamino, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, [C 1 -C 6 alkyl] carbonyl, [alkoxy (CrC 6)] carbonyl, monoalkylaminocarbonyl (Ci-Cß), dialkylaminocarbonyl ( CrC), N-15 alkanoylamino (C? -C6), or N-alkanoyl (C? -C4) -N-alkylamino (C? -C), each of the last 13 mentioned radiols are unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, carboxyl, cyano, thiocyanate, alkoxy (CrC4), halogenoalkoxy (CrC4), alkylthio (CrC4), haloalkylthio (C? -C4), monoalkylamino (CrC), dialkylamino (C -? - C4), cycloalkyl (C3-Cg), cycloalkylamino (C3-Cg), [ alkyl (C? -C4)] carbonyl, [(C? -C4) alkoxy] carbonyl, aminocarbonyl, monoalkylaminocarbonyl (C? -C4), dialkylaminocarbonyloylC-? C4), phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclicthio and heterocyclylamino, each of the last 8 mentioned radicals are unsubstituted or have one or more substituents selected from the group consisting of halogen, nitrogen, cyano alkyl 5 ( C-1-C4), alkoxy (CrC), alkylthio (CrC4), halogenoalkyl (CC), halogenoalkoxy (C4), formyl, alkylcarbonyl (C4) and alkoxycarbonyl (C -? - C), or is cycloalkyl (C3-Cg), cycloalkoxy (C3-Cg), cycloalkylamino (C3-Cg), phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclicthio or heterocyclylamino, each of the last 11 mentioned radicals are not substituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, carboxyl, cyano, thiocyanate, alkyl (C? -C), haloalkyl (CrC) , alkoxy (C -? - C4), haloalkoxy (C? -C4), alkyl (CrC4), haloalkylthio (C? -C4), monoalkylamino (C? -C4), dialkylamino (C? -C4) ), (C3-Cg) cycloalkyl, [(C [beta] -C4) alkylcarbonyl, [(C4C) alkoxy] carbonyl, aminocarbonyl, monoalkylaminocarbonyl (CrC4) and dialkylaminocarbonyl (Cr C4), or two adjacent X radicals which together are a fused ring having 4 to 6 ring atoms and is carbocyclic or containing ring heteroatoms selected from the group consisting of O, S and N and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, alkyl and oxo (C 1 -C 4), n is 0, 1, 3, 4 or 5, preferably 0, 1, 2, 3 or 4, in particular 1 or 2 and heterocyclyl in the aforementioned radicals independently of each other and is in each case a radical M * *. * ***, * »**. **. t. . -r .t-i, -. ^, ..,,. . "Heterocyclic having from 3 to 7 ring atoms and 1 to 3 heteroatoms selected from the group consisting of N, O and S, wherein a) the total carbon atoms of the radicals A1 and A2-R2 add up to at least 6 carbon atoms or b) the total of the carbon atoms in the radicals A1 and A2-R2 5 adds up to 5 carbon atoms and A1 is a group of the formula -CH2- or -CH2CH2- and R1 is alkyl (C-? -C4), halogenoalkyl (CrC4), haloalkenyl (C2-C6) or cycloalkyl (C3-Cg) which is unsubstituted or substituted. Unless specified in more detail, the divalent radicals, for example B1 = -C (= Z *) - Z ** -, are defined in such a way that, in the 10 groups of mixed compounds, for example, -B1 -D1, that link of the divalent radical is linked to the group D1 that appears on the right side of the formula for the divalent radical, ie -B1-D1 is a group of the formula - C (= Z *) - Z ** - D1; a similar definition applies to analogous divalent radicals. The compounds of the formula (I) can form salts when a basic group such as, for example, aminc or alkylamino undergoes an addition reaction with a suitable inorganic or organic acid, such as, for example, HCl, HBr, H2SO4 or HNO3, but also oxalic acid or sulfonic acid. Suitable substituents that are present in deprotonated form, such as, for example, sulfonic acids or carboxylic acids, can form internal salts with those groups that have the ability to undergo protonization on their own, such as amino groups. In addition, the salts can be formed by replacing, in the case of suitable substituents such - ************* * > . . t *. . *TO . . «.-. . . ,. . . » * "". . . . . . " »-«,. , > ^: as, for example, sulfonic acids or carboxylic acids, hydrogen by an agriculturally suitable cation. Examples of such salts are metal salts, particularly alkali metal salts or alkaline earth metal salts, in particular sodium salts and potassium salts, or furthermore ammonium salts, salts with organic amines, or quaternary ammonium salts. In the formula (I) and in all the following formulas, the alkyl, alkoxy, halogenoalkyl, haloalkoxy, alkylamino and alkyl radicals and the corresponding unsaturated and / or substituted radicals can be straight or branched chain in the carbon structure in each case. Unless you In other words, lower carbon structures, for example those having 1 to 6 carbon atoms or in the case of unsaturated groups, those having 2 to 6 carbon atoms, are preferred for these radicals. The alkyl radicals, in addition to the meanings of compounds such as alkoxy, haloalkyl and the like, are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyl, such as n-hexyl, i-hexyl and 1,3-dimethyl Jethyl. , heptyls such as n-heptyl radicals, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl having the meanings of the unsaturated radicals which are possible and which may correspond to the alkyl radicals; for example alkenyl is allyl, 1- 20 methylprop-2-en-1-yl, 2-methylprop-2-en-yl, but-2-en-1-yl, but-3-en-1-yl, - methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl; Alkynyl is, for example, propargyl, but-2-yl-1-yl, but-3-yl-1-yl, 1-methylbut-3-yl-1-yl. ?? mM ^ á? u ^^. MMbÉ ^ MfiMltf ^^ üÉMáiittÉlMtfü ^ áfl Cycloalkyl is a carbocyclic saturated ring system that preferably has 3-8 carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Substituted cycloalkyl includes cyclic systems with substituents, which substituents are linked to the cycloalkyl radical by a double bond, for example an alkylidene group such as methylidene. Substituted cycloalkyl also includes polycyclic aliphatic systems such as, for example, bicyclo [1.1.0] butan-1-yl, bicyclo [1.1.0] butan-2-yl, bicyclo [2.1.0] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-ylo-adamantan-1-yl and adamantan-2-yl. Cycloalkenyl is a carbocyclic non-aromatic, partially unsaturated ring system preferably having 4-8 carbon atoms, for example 1-cyclobutenium, 2-cyclobutenyl, 1-cyclopentyl, 2-cyclopentyl, 3-cyclopentenyl, or 1-cyclohexenyl. , 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl. The explanations Those which are provided for the cycloalkyl apply analogously to the substituted cycloalkenyl. Halogen is, for example, fluorine, chlorine, bromine or iodine. Halogenoalkyl, -alkenyl and -alkynyl is alkyl, alkenyl or alkynyl which are partially or totally substituted by halogen, preferably fluorine, chlorine, And / or bromine, in particular by fluorine or chlorine, for example monohaloalkyl, perhaloalkyl, CF3, CHF2, CH2F, CF3CF2, CH2FCHCI, CCI3, CHCI2, CH2CH2CI; halogenoalkoxy is, for example, OCF3, OCHF2, OCH2F, CF3CF20, OCH2CF3 and OCH2CH2CI; this applies analogously to halogenoalkenyl and other halogen-substituted radicals. Aryl is a mono-, bi- or polycyclic aromatic system, for example, phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl. A heterocyclic radical or ring (heterocyclyl) can be saturated, unsaturated or heteroaromatic; preferably it contains one or more in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably selected from the group consisting of nitrogen, oxygen and sulfur; it is preferably an aliphatic heterocyclic radical having from 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms. The heterocyclic radical can be, for example, a heteroaromatic radical or ring (heteroaryl) such as, for example, a mono-, bi- or polycyclic aromatic system in which at least one ring contains one or more heteroatoms, for example pyridyl , pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, furyl, pyrrolyl, pyrazolyl, imidaiolyl and triazolyl or is a partially or totally hydrogenated radical such as oxiranyl, oxetanyl, oxalanyl (= tetrahydrofuryl), oxanyl, pyrrolidyl, piperidyl, piperazinyl, dioxalanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl and morpholinyl. Suitable substituents for a substituted heterocyclic radical are those mentioned below and also also oxo. The oxo group can also occur in those ring heteroatoms that may exist in various stages of oxidation, for example in the case of nitrogen and sulfur. Substituted radicals such as alkyl, alkenyl, alkynyl, aryl, phenyl, benzyl, heterocyclyl and substituted are, a substituted radical that is derived from the unsubstituted or substituted structure, the substituents having, for example, one or more, preferably 1 , 2 or 3, radicals selected from the group consisting of halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitrogen, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino such as acylamino , mono- and dialkylamino and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl and, in the case of cyclic radicals, also alkyl and haloalkyl; the term "substituted radicals" such as substituted alkyl and the like include, in addition to the above-mentioned saturated hydrocarbon-containing radicals, which correspond to aliphatic and aromatic unsaturated radicals such as substituents, such as optionally alkenyl, alkynyl, alkenyloxy, alkynyloxy, phenyl, phenoxy and similar. In the case of cyclic radicals substituted with aliphatic portions in the ring, the definition also includes cyclic systems with those substituents which are linked to the ring by means of a double bond, for example by means of an alkylidene group such as methylidene or ethylidene. In the case of radicals having carbon atoms, those having 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, are preferred. Preferred substituents are, as a rule, those selected ^^ * ^ of the group consisting of halogen, for example fluorine and chlorine, alkyl (C? -C), preferably methyl or ethyl, haloalkyl (C? -C4), preferably trifluoromethyl, alkoxy (CrC4), preferably methoxy or ethoxy, halogenoalkoxy (CrC4), nitrogen and cyano. Particularly preferred substituents are methyl, methoxy and chloro. Amino mono- or disubstituted is a chemically stable radical selected from the group consisting of substituted amino radicals that are unsubstituted, for example, by one, or two identical or different radicals selected from the group consisting of alkyl, alkoxy, acyl or aryl; preferably monoalkylamino, dialkylamino, acylamino, arylamino, N-alkyl-N-arylamino and N-heterocycles; alkyl radicals having 1 to 4 carbon atoms are preferred; aryl is preferably phenyl or substituted phenyl; acyl is protected by the definition given below, preferably alkanoyl (C? -C4). This applies analogously to hydroxylamino or substituted hydrazino. Optionally substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, by identical or different related radicals from the group consisting of halogen, (C 1 -C 4) alkyl, alkoxy (CrC 4), haloalkyl ( CrC4), halogenoalkoxy (CrC) and nitrogen, for example o-, m- and p-tolyl, dimethylphenyls. 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro- and -trichlorophenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, or-, m- and p-methoxyphenyl. i, i * - * An acyl radical is the radical of an organic acid, for example a radical of a carboxylic acid and acid radicals derived therefrom, such as thiocarboxylic acid, optionally n-substituted iminocarboxylic acids or the carbon monoester radical , optionally n-substituted carbamic acid, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids. Acyl is, for example, formyl, alkylcarbonyl such as [(C 1 -C 4) alkylcarbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other organic acid radicals. The radicals can be further substituted in each case in the alkyl or phenyl portion, for example in the alkyl portion by one or more radicals selected from the group consisting of halogen, alkoxy, phenyl and phenoxy; Examples of substituents on the phenyl portion are those substituents which have already been mentioned above in general terms for substituted phenyl. The invention also relates to all the stereoisomers included in the formula (I) and mixtures thereof. Said compounds of the formula (I) contain one or more asymmetric carbon atoms or in addition double bonds, which are not specifically indicated in the formula (I). Formula (I) includes all stereoisomers that are possible and that are defined by their specific space form, such as enantiomers, diastereomers, Z- and E-isomers, and can be obtained from mixtures of stereoisomers by customary or similar methods prepared by ü | ^^^ ^ ** - ^ - > means of stereoselective reactions in combination with the use of stereochemically pure starting materials. The compounds of the above-mentioned formula (I) according to the invention, or their salts which are of particular interest, mainly due to their more potent herbicidal action, better selectivity and / or because it is easier to prepare them, are those wherein the individual radicals have one of the preferred meanings that have already been mentioned above or are mentioned hereinafter, or in particular those in which one or more of the preferred meanings that have already been mentioned above or which are mentioned in the present below are combined with each other. R1 is preferably phenyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, carboxyl, sulfo, cyano, thiocyanate, (C4) alkyl, haloalkyl (CrC4), (C? -C4) alkoxy, haloalkoxy (C? -C4), alkylthio (CrC4), halogenoalkylthio (CrC4), monoalkylamino (C? -C4), dialkylamino (CrC4), cycloalkyl (C3-Cg), carbonyl [(C? -C4) alkyl], carbonyl [alkoxy (CrC4)], aminocarbonyl, monoalkylaminocarbonyl (C? -C4), dialkylaminocarbonyl (C? -C4), alkylsulfonyl (CrC4) and halogenoalkylsulfonyl (C? -C4), and which, even the substituents, have from 6 to 30 carbon atoms preferably from 6 to 20 carbon atoms. carbon, in particular 6 to 15 carbon atoms.

UaajMttua "• - - '- - --- * - - -' • • • - - - - - -" • - ----- - • - • • -. - »-» • • * • ..,.

R1 is also preferably (C3-Cg) cycloalkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, cyano, thiocyanate, alkyl (C? -C), haloalkyl (CrC4) , (C -? - C4) alkoxy, haloalkoxy (CrC4), alkylthio (CrC4), haloalkylthio (C? - C4), monoalkylamino (CrC4), dialkylamino (CrC) and which, even the substituents, have from 3 to 30 carbon atoms, preferably from 3 to 20 carbon atoms, in particular from 3 to 15 carbon atoms. R1 is also preferably heterocyclyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, carboxyl, sulfonyl, cyano, thiocyanate, alkyl (CrC4), haloalkyl (C? -C4), alkoxy (C -? - C4), haloalkoxy (CrC4), alkylthio (CrC4), haloalkylthio (CrC4), monoalkylamino (C? -C4), dialkylamino (CrC4), cycloalkyl (C3-C9), carbonyl [ alkyl (CrC4)], carbonyl [alkoxy (CrC4)], aminocarbonyl, monoalkylaminocarbonyl (CrC4), dialkylaminocarbonyl (CrC4), alkylsulfonyl (CrC4) and haloalkylsulfonyl (CrC4), and which, even the substituents, have 2 to 30 carbon atoms. carbon, preferably 2 to 20 carbon atoms, in particular 2 to 15 carbon atoms. Here and also in other radicals, heterocyclic is preferably a heterocyclic radical having from 3 to 7, in particular 3 to 6, ring atoms and a heteroatom selected from the group consisting of N, O and S, for example pyridyl, thienyl , furyl, pyrrolyl, oxiranyl, oxetanyl, oxolanyl, i MaR, ^ .. (= tetrahydrofuryl), oxanyl, pyrrolidyl, piperidyl, or is a heterocyclic radical having two or three heteroatoms selected from the group consisting of pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl, morpholinyl. R1 is also preferably (C -? - C6) alkyl, (C2-C6) alkenyl or (C2-C6) alkynyl, each of the last 3 radicals mentioned is unsubstituted or substituted by one or more radicals selected from the group consisting of group consisting of halogen, hydroxyl, cyano, nitrogen, thiocyanate, alkoxy (CrC4), halogenoalkoxy (CrC4), alkenyloxy (C2-C4), halogenoalkenyloxy (C2-C4), alkylthio (CrC4), alkylsulfinyl (CrC4), alkylsulfonyl ( C2-C4), halogenoalkylsulfinyl (C? -C4), haloalkylsulfonyl (CrC4) and (C3-C6) cycloalkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, cyano, thiocyanate, (C? -C4) alkyl, haloalkyl (C? -C4), (C? -C) alkoxy, haloalkoxy (CrC4), alkyl C? -C4), haloalkylthio (CrC4), monoalkylamino (CrC4) and dialkylamino ( C? -C4) and phenyl and heterocyclyl, each of the last two mentioned radicals are not substituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, carboxyl, sulfonyl, cyano, thiocyanate, alkyl (C -? - C4), halogenoalkyl (C? - C4), alkoxy (CrC), halogenoalkoxy (C -? - C4), alkylthio (CrC4), haloalkylthio (C? -C4), monoalkylamino (C? -C4), dialkylamino (CrC4), cycloalkyl (C3-Cg), carbonyl [(C? -C4) alkyl], carbonyl [alkoxy (CrC4)] ], . . *? . t ^? . . «, *. . . -. . . -. . > ^ i »». .,. . ^ - ^ -. . . - v - - ~. . , ^ M? I ^? aminocarbonyl, monoalkylaminocarbonyl (C -? - C4), dialkylaminocarbonyloid-C4), alkylsulfonyl (C? -C4) and haloalkylsulfonyl (C? -C4), and radicals of the formulas R'-C (= Z) - , R'-C (= Z ') - Z-, R'-ZC (= Z') -, R'R "-C (= Z ') -, R'-ZC (= Z') - O- , R'R "NC (= Z ') - Z-, R'-ZC (= Z') - NR" - and R, R "NC (= Z,) - NR" '-, in which R' , R "and R '" in each case independently of one another are alkyl (CrC4), phenyl, alkylphenyl (C4), cycloalkyl (C3-C6) or cycloalkyl (C3-C6) -alkyl (CrC4), each of the last 5 mentioned radicals are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, cyano, thiocyanal, alkoxy (CrC4), alkylthio (CrC), monoalkylamino (CrC4), dyalkylamine (C? -C), alkenyl (C2-C), alkynyl (C2-C4), cycloalkyl (C3-C6) and in the case of cyclic radicals also alkyl (C? -C) and haloalkyl (C? -C), and in which Z and Z 'independently of each other are in each case an oxygen or sulfur atom, and which, even the substituents, preferably have from 1 to 20 carbon atoms, in particular from 1 to 15 carbon atoms, R1, preferably alkyl (C -? - C4) ) which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C? -C4) alkoxy, alkylthio (C? -C4), alkylsulfonyl (C? -C4), cycloalkyl (C3-Cg) , which is unsubstituted or substituted, and phenyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, alkyl (CrC4) and halogenoalkyl (C -? - C4), alkoxy (CrC4), haloalkoxy (C C4), alkylthio (CrC4), ami no, mono- and diamino [alkyl (Cr C4)], alkanoylamino (C? -C4), benzoylamino, nitrogen, cyano, carbonyl [(C? -C4) alkyl], carbamoyl formyl, mono- and diaminocarbonyl [alkyl (C ? -C4)] and alkylsulfonyl (C? -C4) and heterocyclic with 3 to 6 ring atoms and 1 to 3 ring heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, alkyl (CrC4) and oxo, or phenyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, carboxyl, sulfonyl , cyano, thiocyanate, alkyl (CrC4), halogenalkyl (C? -C4), alkoxy (C? -C4), halogenoalkoxy (C? -C4), alkylthio (C? -C), haloalkylthio (CrC4), monoalkylamino (C) ? -C), dialkylamino (C? -C4), cycloalkyl (C3-C9), [alkyl (CrC4)] carbonyl, [(C -? - C) alkoxy] carbonyl, aminocarbonyl, monoalkylaminocarbonyl (C -? - C4) , dialkylamino bonyl (CrC4), alkylsulfonyl (C? -C), and haloalkylsulinyl (CrC4), and which, even the substituents, have 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, in particular 2 to 15 carbon atoms. R1 furthermore as preferred is alkyl (CC), haloalkylbenzyl (CrC4), or [(C3-C6cycloalkyl)] -alkyl (C? -C2), in particular (C-? - C4) alkyl, haloalkyl (C? -C4) ), or [(C3-C6) cycloalkyl] methyl, preferably -CH3, -CH2F, -CHF2, -CF3, CH2Cl, -CHCI2, CCI3, -CH2Br, -CHBR2, -CH2CH3, -CH2CH2F, -CF2CHF2, - CH 2 CH 2 Cl, -CH 2 CH 2 Br -CH (CH 3) 2, -CF (CH 3) 2, -C (CH 3) 2 Cl, -CG 2 CH 2 CH 2 F, -CH 2 CH 2 CH 2 Cl or cyclopropylmethyl. ^ Ün ^^ ü-UMÉ-W The following meanings of R2 are of particular interest, independently of the radicals R1, R3, R4, A1, A2 and (X) n and preferably in combination with preferred meanings of one or more of these radicals: R2 is preferably (C3-Cg) cycloalkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of radicals A), B), C) and D), wherein: Group A) it is composed of the radicals halogen, hydroxyl, amino, nitrogen, formyl, carboxyl, aminocarbonyl, sulfo, cyano, thiocyanate and oxo, group B) is composed of the C-alkyl radicals), radicals of the formulas alkyl (C-? -C6), alkylthio (C -? - C6), monoalkylamino (Cr Cß), dialkylamino (C? -C4), alkenyl (C? -C6), alkynyl (C2-C6), cycloalkyl (C3-C9), cycloalkenyl (C -Cg), alkylidene (C -? - C6), cycloalkylidene (C4-Cg), R'-C (= Z ') -, R'-C (= Z') - ZC (= Z ') -, R, R "NC (= Z') -) R! -ZC (= Z ') - O-, R'R" NC (= Z') - Z-, R'-ZC (= Z '= - NR "- and R'R" NC (= Z') - NR '"- in do n of R ', R "and R'" in each case independently of one another are alkyl, phenyl (C C6), phenylalkyl- (CrC6), cycloalkyl (C3-C9) or cycloalkyl (C3-Cg) -alkyl (CrC6) and wherein Z and Z 'independently of each other are in each case an oxygen or sulfur atom, group C) is composed of radicals as shown for group B), but each radical being replaced by one or more selected radicals of the group consisting of halogen hydroxyl, amino, nitrogen, formyl, carboxyl, sulfo, cyano, thiocyanate, alkoxy (CrC4), halogenoalkoxy (d- ^ ^ ^ Mül ^ y ^ M ^ MM ^^ nn ^ j C4), alkylthio (C4), haloalkyl (C1-C4), monoalkylamino (CrC4), dialkylamino (C1-C4), cycloalkyl (C3-Cg), cycloalkylene (C4-Cg), cycloalkylidene (C4-Cg), [alkyl (CrC4)] carbonyl, [(C? -C4) alkoxy] carbonyl, aminocarbonyl, monoalkylaminocarbonyl (CrC4), dialkylaminocarbonyl, phenyl, phenoxy, phenylthio , phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio and heterocyclylamino, each of the last mentioned 21 radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitrogen, cyano, alkoxy (CrC4), alkylthio (CrC4) , (C 1 -C 4) halogenoalkoxy, formyl, alkylcarbonyl (C 1 -C 4) and alkoxycarbonyl (Cr C4), and in the case of cyclic radicals, furthermore alkyl (C? -C), haloalkyl (CrC4), and alkylidene (C? -C), and in the case of cyclic radicals in addition, alkyl (Ci-Cß) , halogenoalkylide-Cß) and alkylidene (C -? - C6), and group D) is composed of divalent or trivalent aliphatic bridges having from 1 to 6, preferably from 1 to 4, carbon atoms which, in the case of divalent bridges, connect two and in the case of trivalent bridges three carbon atoms of the cyclic eructure and the radical R2 therefore represents the radical of a bicyclo or tricycle, each of the bridges being unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, nitrogen, cyano, Alkyl (C? -C4), (C4) alkoxy, alkylthio (CrC4), haloalkyl (CrC4), halogenoalkoxy (CrC4) formyl, alkylcarbonyl (CrC4), alkoxycarbonyl (C4), and oxo, and where R2, including the substituents preferably have 3 to 20 carbon atoms, in particular 3 to 15 carbon atoms. The radicals Preferred cycloalkyl (C3-Cg) are cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, in particular cyclopropyl, cyclobutyl or cyclopentyl. R2 is preferably also (C4-Cg) cycloalkenyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of radicals A), B), C) and D) and as defined as radicals for R2 = cycloalkyl (C3-Cg), and even substituents, preferably have from 4 to 20 carbon atoms, in particular 4 to 15 carbon atoms. Preferred (C4-Cg) cycloalkenyl radicals are 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl and 3-cyclopentenyl. R 2 is preferably also heterocyclic which is unsubstituted or substituted by one or more radicals selected from the group consisting of radicals A), B), C) and D) as they are defined as radicals for R2 = cycloalkyl (C3-C9). Heterocyclyl in this context is preferably a heterocyclic radical having from 3 to 6 of all those in the group consisting of pyridyl, thienyl, furyl, pyrrolyl, oxiranyl, 2-oxetanyl, 3-oxetanyl, oxolanyl (= tetrahydrofuryl), pyrrolidyl. , piperidyl, in particular oxiranyl, 2-oxetanyl, 3-oxetanyl or oxolanyl, or is a heterocyclic radical having two or three heteroatoms, for example pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl , triazolyl, piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl or morpholinyl. "" • ~ 'ff- ^ M.

R2 is also preferably phenyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of the radicals A), B) and C) as defined for the radicals of R2 = (C3-C9) cycloalkyl. R 2 even substituents, preferably have up to 20 carbon atoms, in particular up to 15 carbon atoms, and very especially up to 10 carbon atoms. R2 is preferably (C3-Cg) cycloalkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of radicals A), B), C) and D), wherein Group A) is composed of the radicals halogen, hydroxyl, nitrogen, formyl, aminocarnyl, cyano and thiocyanate, Group B) is composed of the radicals alkoxy (C? -C), alkylthio (CrC4), monoalkylamino (C? -C4), dialkylamino ( CrC4), alkenyl (C2-15 C), alkynyl (C2-C4), cycloalkyl (C3-C6), cycloalkenyl (C4-C6), alkylidene (C4), cycloalkylidene (C4-C6), radicals of the formulas R '-C (= Z, R'-C (0') -Z-, R'-ZC (= Z, R'R "NC (= Z, R'-ZC (= Z ') - 0-, R 'R' NC (= Z ') - Z-, R'-ZC (= Z NR "- and R'R" NC (= Z') - NR '"- where R', R" and R '" in each case independently of one another are alkyl (C? -C4), phenyl, phenyl-alkyl (C? -C4), cycloalkyl (C3-C6), or cycloalkyloICrC?), and wherein Z and Z 'independently one or from another are in each case an atom of oxygen or sulfur, group C) is composed of the radicals as shown in group B), but each radical is substituted by one or more radicals selected from the group consisting of halogen, alkoxy (CrC4), halogenoalkoxy (C4), alkylthio (C) C4), haloalkyl (C? -C4), 5-monoalkylamino (C? -C4), dialkylamino (CrC4), cycloalkyl (C3-C6), [alkyl (Cr C)] carbonyl, [alkoxy (CrC4)] carbonyl, aminocarbonyl , monoalkylaminocarbonyl (CrC4), dialkylaminocarbonyl (C? -C4), phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclicthio and heterocyclylamino wherein each of the last 8 mentioned radicals is unsubstituted or has one or more selected substituents of the group consisting of halogen, nitrogen, cyano, alkyl (C -? - C4), alkoxy (CrC), alkylthio (CrC4), halogenoalkyl (C? - C4), halogenoalkoxy (CrC4), alkylcarbonyl (CrC4) and alkoxycarbonyl ( C? -C4), and group D) is composed of divalent aliphatic bridges that connect two carbon atoms of the cyclic structure, radical R2 therefore represents the radical of a bicyclo, for example bicyclo [1.1.0] butan-1-yl-bicyclo [1.1.0] butan-2-yl, bicyclo [2.1 .0] pentane-1-yl, bicyclo [2.1.0] pentan-2-yl or bicyclo [2.1.0] pentan-5-yl, wherein each of the bridges is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C? -C4) alkyl, alkoxy (CrC), alkylthio (CrC4), haloalkyl (CrC4), haloalkoxy (C? -C4), alkylcarbonyl (CrC4), alkoxycarbonyl (CrC) and oxo.

J & * aUaat '^ - - ^ - - - - - - - J- -, ------ »- ^ - - ...,, - 5, 0 ^^ - R2 is very special and preferable (C3-Cg) cycloalkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, thiocyanate, alkyl (C? -C), haloalkyl (CrC4), alkoxy (C ? -C4), halogenoalkoxy (C? -C4), alkylthio (CrC4), 5-haloalkylthio (C? -C), alkylidene (CrC4), monoalkylamino (CrC4) and dialkylamino (CrC4) or heterocyclic or phenyl, each of The last two mentioned radicals are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, carboxyl, sulfonyl, cyano, thiocyanate, alkyl (CrC4), Halogenoalkyl (C? -C4), alkoxy (CrC), haloalkoxy (CrC4), alkylthio (C? -C4), haloalkylthio (CrC4), monoalkylamino (C? -C4), dialkylamino (C? -C4), (C3-C6) cycloalkyl, heterocyclyl [(CrC4) alkyl] carbonyl, [(CrC4) alkoxy] carbonyl, aminocarbonyl, monoalkylaminocarbonyl (C? -C4), dialkylaminocarbonyl (CrC4), alkylsulfonyl (C4) and halogenoalkylsulfonyl (CrC4). The following meanings of R3 are of particular interest, independently of the radicals R1, R2, R4, A1, A2 and (X) n and preferably in combination with preferred meanings of one or more of these radicals: R3 is, for example, hydrogen, alkyl (C? -C4), which is unsubstituted Or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, cyano, thiocyanate, alkoxy (CrC4), halogenoalkoxy (C -? - C4), alkylthio (C? -C), haloalkylthio (CrC4) , monoalkylamino (C? -C4) and dialkylamine (C? -C), or phenyl or cycloalkyl (C3-C6), each of the last 2 mentioned radicals are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, carboxyl, sulfonyl, cyano, thiocyanate, alkyl (C? -C4), halogenoalkyl (C? -C4), alkoxy (CrC4), haloalkoxy (C? -C4), alkylthio (CrC4), haloalkylthio (CrC4), monoalkylamino (C? -C4), dialkylamino (C? -C4), cycloalkyl (C3) -Cg), carbonyl [alkyl (CrC4)], carbonyl [(C?-C4) alkoxy], aminocarbonyl, monoalkylaminocarbonyl (CrC4), alkylsulfonyl (C?-C4) and haloalkylsulfonyl (C?-C4), or a radical of the formula N (BD1) (B2-D2) wherein B1, B2, D1 and D2 are as already defined or preferably as defined below, in particular amino. The following meanings of R4 are of particular interest, independently of the radicals R1 to R4, A1, A2 and (X) n and preferably in combination with preferred meanings of one or more of these radicals: R4 is, for example, a radical of the formula -B3-D3 wherein B3 and D3 are preferably as defined below: R4 is preferably hydrogen, (C? -C4) alkyl, phenyl or (C3-C6) cycloalkyl, each of the last 3 radicals not substituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, carboxyl, sulfonyl, cyano, thiocyanate, alkoxy (C -? - C4), halogenoalkoxy (C? -C4), alkylthio (C -? - C4), haloalkylthio (CrC), monoalkylamino (C? -C), dialkylamino (CrC4), cycloalkyl (C3-C9), carbonyl [(C? -C4) alkyl], carbonyl [alkoxy (C -? - C4)], The aminocarbonyl, monoalkylaminocarbonyl (C?-C4), dialkylaminocarbonyl (C?-C) and alkylsulfonyl (C?-C4), haloalkylsulfortyl (C?-C4), and in the case of cyclic radicals furthermore alkyl (C C) ? -C4) and halogenoalkyl (C? -C) or formyl, carbonyl [(C? -C) alkyl], carbonyl [(C? -C4) alkoxy], aminocarbonyl, -monoalkylaminocarbonyl (C? -C4) or dyalkylaminocarbonyl (C? -C4); in particular hydrogen, methyl, ethyl, n-propyl or isopropyl especially and preferably hydrogen. The following meanings of A1 are of particular interest, independently of the radicals R1 to R4, A2 and (X) n, and preferably in The combination with preferred meanings of one or more of these radicals: A1 is straight chain alkylene having 1 to 5 carbon atoms or straight chain alkenylene or alkynylene, each of which has 2 to 5 carbon atoms, each of the last three mentioned divalent radicals are substituted or unsubstituted by one or more radicals selected from the group consisting of halogen, nitrogen, cyano, thiocyanate and a radical of the formula -B4-D4, B4 is a direct bond or a divalent group of the formulas -O-, -SO2-, -CO-, -O-CO-, -NR ° -, - NR ° -CO-, -CO-NR0-, -O-CO-NR0- or -NR ° CO- CO-, where R ° and D4 independently of one another are in each case Hydrogen, alkyl (C? -C4), phenyl, phenylalkyl (C? -C4), cycloalkyl (C3-C4) or cycloalkyl (C? -C4) -alkyl (C? -C4), each of the The last 5 mentioned radicals are substituted or unsubstituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, ^. ^^ ii ^^^, ^ nitrogen, formyl, carboxyl, sulfonyl, cyano, thiocyanate, (C4) alkoxy, haloalkoxy (C -? - C4), alkylthio (CrC4), haloalkylthio (CC), monoalkylamino (C) C4), dialkylamino (C? -C), cycloalkyl (C3-Cg)carbonyl [(C? -C) alkyl], carbonyl [(C? -C) alkoxy], aminocarbonyl, monoalkylaminocarbonyl (C? -C), dialkylaminocarbonyl (CrC4), alkylsulfonyl (CrC), haloalkylsulfonyl (CrC), and in the case of cyclic radicals also alkyl (CrC4) and halogenoalkyl (C? -C4). A1 is preferably a radical of the formula -CH2-, -CH2CH2-, - CH2CH2CH2-, - CH2CH2CH2CH2 or -CH2CH2CH2CH2CH2- which is not substituted. In addition, the preferred one is one of the above radicals which is substituted by one or more of the above-mentioned radicals -B4-D4.A1 which is especially preferably a radical of the formula -CH2CH2- or -CH2CH2CH2- which is substituted or not substituted by one or two radicals of the hydroxyl, alkyl (CrC4) or alkoxy (CrC) formula. The following meanings of A2 are of particular interest, independently of the radicals R1 to R4, A1 and (X) n and preferably in combination with preferred meanings of one or more of these radicals. A2 is preferably a direct bond or a group of the formula -CH2-, -CH2CH2-, -CH2CH2CH2-, - CH2CH2CH2CH2, each of the last 4 divalent radicals mentioned above are substituted or unsubstituted by one or more selected radicals of the group consisting of halogen, nitrogen, cyano, thiocyanate and radicals of the formula -B5-D5- or a divalent radical of the formula V1, V2, V3, V4 or V5, '* * * *' * "'******' • '* • * J"' • "" '- "" - ~ - * - "*"' "'-'» '"- < > ** »* < > • > "-CR6R7-W * -CR8R9 (V1) -CR10R11-W * -CR12R13-CR14R15- (V2) -CR16R17-CR18R19-W * -CR20R21- (V3 -CR 22 R23-CR24R25-W * (V4) -CR26R27 -W * (V5) Wherein each of the radicals R6 to R27 in each case independently of one another is hydrogen, halogen, nitrogen, cyano, thiocyanate or a radical of the formula -B6-D6, W * is in each case oxygen, sulfur or a group of the formula N (B7-D7) and B5, B6, B7, D5, D6 and D7, and are as defined below, 10 A2 is especially preferably a direct link or a group of the formula -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, -CH2-O-CH2-, -CH2_O-CH2-CH2-, -CH2-S-CH2-, -CH2-S-CH2- CH2-, -CH2-CH2-S-CH2-, -CH2-NH-CH2-, -CH2-NH-CH2-CH2-, -CH2-CH2-NH-CH2-, -CH2-N (CH3) -CH2 -, -CH2- N (CH3) -CH2-CH2- or -CH2-CH2-N (CH3) -CH2-. B1, B2, B3, and B7 are preferably in each case independently of one another a direct bond or a divalent group of the formulas -C (= Z *) -, -C (= Z *) - Z * \ -C (= Z *) - NH- or -C (= Z *) - NR * - where Z * = oxygen or sulfur, Z ** = oxygen or sulfur and R * = alkyl (C? -C4), phenyl, phenyl-alkyl (C? -C), cycloalkyl (C3-C6) or cycloalkyl (C3-C6) -alkyl (CrC4) where 20 each of the last 5 radicals mentioned is substituted or unsubstituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, carboxyl, sulfo, cyano, thiocyanate, alkoxy (CrC4), ^^ Ü ^ mi ^ i * ^^ ** Í »m? + Má --- i > m *? p. »,, ,, > ,? i iiinm ii lihm ii II mi mi i intu intu, TÍGH H mi Mí ilrft 1ilii.il] iriíii halogenoalcoxi (C? -C4), alkylthio (C? -C), haloalkylthio (CrC4), monoalkylamino (CrC), dialkylamino (CrC4), (C3-Cg) cycloalkyl, carbonyl [(C4) alkyl], carbonyl [(C4) alkoxy], aminocarbonyl, monoalkylaminocarbonyl (CrC4), dialkylaminocarbonyl (CrC4), alkylsulfonyl (CrC4), haloalkylsulfonyl (CrC4) and in the case of cyclic radicals also alkyl (CrC4) and halogenoalkyl (CrC4); It is furthermore preferred for B1, B2, B3 and B7 independent of one another to be a direct bond or a divalent group of the formulas -C (= Z *) -, -C (= Z *) - Z ** -, - C (= Z *) - NH O -C (= Z *) - NR * -, where Z * = O or S, Z ** = O or S and R * = alkyl (C? -C4), phenyl, alkylphenyl (C? -C4), cycloalkyl (C3-C6) or cycloalkyl (C3-C6) -alkyl (CrC4), wherein each of the last 5 radicals mentioned is unsubstituted or substituted by one or more radicals selected from the group consists of halogen, hydroxyl, amino, formyl, (C -? - C4) alkoxy, halogenoalkoxy (CrC4), alkylthio (C? -C4), monoalkylamine (CrC4), dialkylamino (C? -C4), cycloalkyl (C3-Cg) ), [(C 1 -C 4) alkylcarbonyl, [alkoxy (Cr C)] carbonyl, aminocarbonyl, monoalkylaminocarbonyl (CrC), dialkylaminocarbonyl (C 1 -C 4) and in the case of cyclic radicals furthermore alkyl (CrC 4) and halogenoalkyl (C? -C), in particular R * = (C? -C) alkyl or (C3-C6) cycloalkyl or in particular R * = alkylphenyl phenyl (C? -C4), where each of the last two radicals mentioned unsubstituted in the phenyl portion or substituted by one or more radicals selected from the group consisting of halogen, alkyl (CrC), haloalkyl (C -? - C4), alkoxy (C? - C) or halogenoalkoxy (C? - C4) . ^ kfab ^ ÁJßlÉfbMih B4, B5 and B6 are preferably in each case independently of one another a direct bond or a divalent group of the formulas -O-, - S (0) p-, -S (O) pO-, - O -S (O) p-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S, -O -CO-O-, -NR ° -, -0-NR0-, -NR ° -0-, -NR ° -CO-, -CO-NR ° -, -O-CO- 5 NR ° - or -NR ° -CO-O-, where P is the integer 0, 1 or 2 and R ° = hydrogen, alkyl (C? -C4), phenyl, alkylphenol (CrC4), cycloalkyl (C3-C6) or cycloalkyl (C3) - C6) -alkyl (CrC4), each of the last 5 radicals mentioned are not substituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, carboxyl, sulfo, cyano, thiocyanate, (C? -C4) alkoxy, haloalkoxy (C? -C4), alkylthio (CrC4), haloalkylthio (CrC4), monoalkylamino (C? -C4), dialkylamino (CrC4), cycloalkyl (C3-Cg) , [(C 1 -C 4) alky] carbonyl, [(C 4 -C 4) alkoxy] carbonyl, aminocarbonyl, monoalkylaminocarbonyl (CrC 4), dialkylaminocarbonyl (Cr C), alkylsulfonyl (CrC), haloalkylsulfonyl (CrC 4) and in the case of cyclic radicals furthermore alkyl (C C4) and haloalkyl (CrC4), and in particular R ° = hydrogen,, (l-alkyl (CrC4) or cycloalkyl (C-C4) or in particular R ° = phenyl or alkylphenyl (CrC4), each of the last two mentioned radicals are not substituted on the phenyl portion or substituted by one or more radicals selected from the group consisting of halogen, (C 20 C4) alkyl, haloalkyl (CrC4), alkoxy (CrC4) or halogenoalkoxy (CrC4). It is further preferred that B4, B5 and B6 independently of one another is a direct bond or a divalent group of the formulas -O-, -S (O) p-, - CO-, -O-CO-, -CO-O -, -S-CO-, -CO-S-, -NR ° -, -NR ° -CO-, -CO-NR0-, -O-CO- NR - or -NR ° -CO-O-, where p is the integer 0, 1 or 2, in particular 0 or 2, and R ° having the above-mentioned meaning very especially H or (C 1 -C 4) alkyl. D1, D2, D3, D4, D5 and D6 independently of each other preferably are hydrogen, C alquilo-alkyloid), phenyl, alkylphenyl (CrC4), cycloalkyl (C3-C6) or cycloalkyl (C3-C6) - Alkyl (C? -C6), each of the last 5 mentioned radicals are unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl , carboxyl, sulfo, cyano, thiocyanato, (C -? - C4) alkoxy, alkylthio (C? -C4), haloalkylthio (CrC), monoalkylamino (CrC), dialkylamino (C? -C), cycloalkyl (C3) -C9), [alkyl (CrC4)] carbonyl, [alkoxy (CrC4)] carbonyl, aminocarbonyl, monoalkylaminocarbonyl (CrC4), dialkylaminocarbonyl (CrC4), alkylsulfonyl (CrC4), haloalkylsulfonyl (C? -C4) and in the case of cyclic radicals furthermore alkyl (C? -C4) and halogenoalkyl (C? -C4). It is further preferred that D1, D2, D3, D4, D5 and D6 independently of one another is alkyl (CrC4), phenyl, alkylphenyl (CrC4), cycloalkyl (C3-C6) or cycloalkyl (C3-C6) -alkyl (C? -C4), each of the last 5 radicals unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, formyl, alkoxy (C? -C4), halogenoalkoxy (CrC4), alkylthio ( CrC4), monoalkylamino (C? -C4), dialkylamino (CrC4), cycloalkyl (C3-Cg), [alkyl (CrC4)] carbonyl, [alkoxy (Cr C)] carbonyl, aminocarbonyl, monoalkylaminocarbonyl (C -C), «^« G »« «* ^« qaM. . . . . "*. *. . -, •. -. , ..? . . ,,. . ,. , -. a ^ xM dialkylaminocarbonyl (C? -C4) and in the case of cyclic radicals furthermore alkyl (C? -C4) and halogenoalkyl (C? -C4), and are, in particular, (C4) alkyl or cycloalkyl (C3-) C6) or phenyl or alkylphenyl (CrC), each of the last two mentioned radicals are not substituted on the phenyl portion or substituted by one or more radicals selected from the group consisting of halogen, alkyl (CC), halogenoalkyl (CrC), alkoxy (CrC4) or halogenoalkoxy (CrC4). The following definitions of (X) n are of particular interest, independently of the radicals R1 or R4, A1 and A2 and preferably in combination with preferred meanings of one or more of these radicals: (X) n is n substituent X, where the X preferably in each case independently of one another are halogen, hydroxyl, amino, nitrogen, formyl, carboxyl, cyano, thiocyanate, aminocarbonyl or alkyl (C -? - C4), alkoxy (C? - C4), alkylthio (CrC) ), monoalkylamino (CrC4), dialkylamino (CrC), alkenyl (C2-C4), alkynyl (C2-C4), [(C? -C4) alkyl] carbonyl, [(C4-alkoxy)] carbonyl, monoalkylaminocarbonyl (CrC4) ), dialkylaminocarbonyl (Cr C4), N-alkanoylamino (C -? - C6) or N-alkanoyl (C? -C- -N-alkylamino) (C? -C4), each of the last 13 radicals mentioned are unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, cyano, thiocyanate, (C -? - C4) alkoxy, halogenoalkoxy (C -? - C4) ), alkylthio (CrC4), monoalkylamino (CrC4), dialkylamino (CrC4), cycloalkyl (C3-C6), cycloalkylamino (C3-C6), [alkyl (C? -C4)] carbonyl, [alkoxy (C -? - C4) )] carbonyl, aminocarbonyl, monoalkylaminocarbonyl (C? -C4), dialkylaminocarbonyl (C? - , C4), phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio and heterocyclylamino, each of the last 8 mentioned radicals are unsubstituted or have one or more substituents selected from the group consisting of halogen, nitrogen, cyano, alkyl (C? -C), alkoxy (C? -C4), alkylthio (CrC4), haloalkyl (C4), halogenoalkoxy (C-? - C4), formyl, alkylcarbonyl (C? -C4) and alkoxycarbonyl (CrC4) , or (C3-Cg) cycloalkyl, phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio or heterocyclylamino, each of the last 9 mentioned radicals are unsubstituted or substituted, preferably not substituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, carbonyl, cyano, thiocyanate, alkyl (C? -C4), halogenoalkyl (CrC), alkoxy (CrC4), haloalkoxy (C? -C4), alkylthio (CrC4), haloalkylthio (CrC4), monoalkylamino (C? -C4), dialkylamino (CrC4), cycloalkyl (C3-C6), [(alkyl) C4)] carbonyl, [(alkoxy (CrC4)] carbonyl, aminocarbonyl, and dialkylaminocarbonyl (CrC4), or two adjacent radicals X together are a fused ring having from 4 to 6 ring atoms and is carbocyclic or contains therein Ring atoms selected from the group consisting of O, S and N and which is not substituted or substituted by one or more radicals selected from the group consisting of halogen, alkyl (C? -C4) and oxo. n is preferably 0, 1, 2 or 3, in particular 1 or 2. (X) n preferably is also n substituents X, wherein the X in each case independently of one another is halogen, hydroxyl, amino ^ "ETHYL Nitrogen, formyl, carbonyl, cyano, thiocyanate, alkyl (CrC4), cyano-alkyl (C4), alkoxy (C4), alkylamino (CC), d1 - [(alkyl (C? -C4)] -amino, halogenoalkyl (C? -C4), hydroxyalkyl (C1-C), alkoxy (C? -C4) -alkyl (C? -C4), halogenoalkoxy (CrC4) -alkyl (C? -C4), alkylthio (C) C4), haloalkylthio (CrC), (C2-C6) alkenyl, (C2-C6) haloalkenyl, (C2-C6) alkynyl, haloalkynyl (C? -C), alkylamino (C? -C4) - alkyl (C? -C4), di - [(alkyl (Cr C)] - amino-alkyl (C -? - C), cycloalkylamino (C3-C6) -alkyl (C? -C), cycloalkyl (C3-Cg) ), heterocyclyl-alkyl (C? -C4) having from 3 to 9 ring elements, the cyclic groups in the last 3 radicals mentioned are not substituted or substituted by one or more radicals, preferably up to three radicals selected from the group consisting of (C? -C) alkyl, halogen and cyano, or phenyl, phenoxy, phenylcarbonyl, phenylcarbonyl-alkyl (C? -C4), alkoxycarbonyl (C? -C4) -alkyl (C? -C4), alkylaminocarbonyl (C? -C4) -alkyl (Cr C4), alkylcarbonyl (C? -C), alkoxycarbonyl (CrC), aminocarbonyl, -alkylaminocarbonyl (C? -C4), phenoxy- (C? -C4) alkyl, phenyl-alkyl (CrC4), heterocyclyl, heterocyclylamino, heterocyclyloxy, heterocyclicthio or one of the last mentioned radicals that is substituted in the acyclic portion, or preferably, in the cyclic portion by one or more radicals selected from the group consisting of halogen, nitrogen, cyano, alkyl (C? -C4), alkoxy (Cr C4), alkylthio (C? -C4), halogenoalkyl (CrC4), haloalkoxy (C? -C4), formyl, alkylcarbonyl (C? -C4), alkoxycarbonyl (CrC4), alkoxy (C4), heterocyclyl in the radicals containing in each case from 3 to 9 ring atoms and 1 to 3 therein, ring atoms selected from the group consisting of N, O and S, EhmiHteiiiu ^ Ai or two adjacent radicals X together is a fused ring having 4 to 6 ring atoms and is carbocyclic or contains hetero ring atoms selected from the group consisting of O, S and N and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, alkyl (CrC4) and oxo. (X) n is especially preferably n substituents X, where X in each case independently of one another is halogen, OH, NO2, CN, SCN alkyl (C? -C4), alkoxy (CrC4), alkylcarbonyl (CrC4) or alkyloxycarbonyl (C? -C4), the last four mentioned radicals are unsubstituted or substituted by halogen or alkoxy (C -? - C), and very especially preferably n substituents X, where X in each case independently of one another is halogen, hydroxyl, alkyl (C? -C4) or alkoxy (Cr-C). Independently of one another, heterocyclyl in the above-mentioned or mentioned radials is preferably a heterocyclic radical having from 3 to 7 ring atoms or 1 to 3 heteroatoms selected from the group consisting of N, O and S, preferably a heteroaromatic radical selected from the group consisting of pyridyl, pyrimidinyl, pyridazinyl, triazinyl, thienyl, thia2: olyl, thiadiazolyl, oxazolyl, isoxazolyl, furyl, pyrrolyl, pyrazolyl, imidazolyl and triazolyl or a partially or fully hydrogenated heterocyclic radical selected from the group which consists of oxiranyl, oxetanyl, oxolanyl (= tetrahydrofuryl), oxanyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl and morpholinyl, say ^ Ufa. The heterocyclyl is especially preferably a heterocyclic radical having from 3 to 6 ring atoms and one (!) Heteroatoms of the group consisting of N, O and S, and in particular a heteroaromatic radical having 5 to 10 carbon atoms. or 6 ring atoms or a saturated or partially unsaturated heterocyclic (non-heteroaromatic) radical having from 3 to 6 ring atoms. In addition, heterocyclyl is preferably a heterocyclic radical having 5 or 6 ring atoms and 2 or 3 heteroatoms selected from the group consisting of N, O and S, in particular pyriridyl pyridazinyl, pyrazinyl, triazinyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl , pyrazolyl, imidazolyl, triazolyl or piperazinyl, dioxolanyl, oxazolinyl, isoxazolidinyl or morpholinyl. Preferably, the number of carbon atoms of the total carbon atoms of the two radicals A1 and A2-R2 is a) at least 6 carbon atoms, in particular 6 to 20 carbon atoms, very especially 6 to 12 atoms of carbon, or b) 5 carbon atoms, in each case A1 = a group of the formula -CH2- or -CH2CH2- and Ft1 = alkyl (C? -C), haloalkyl (C? -C4), haloalkenyl (C2-) C6) or (C3-Cg) cycloalkyl which is unsubstituted or substituted, preferably, haloalkyl (C -? - C4) or (C3-C6) cycloalkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of of alkyl (Cr C4) and alkyl (C4). In particular, the total number of carbon atoms of the radicals A1 and A2-R2 together are one of the aforementioned alternatives of a). ),. -,,.-i. . ,. "-, i,, • -..... . . . . . .... ^,, .- »." •. .t fcA The group of compounds -A2-R2 is preferably cyclopropyl (hereinafter also "c-Pr"), CH2-c-Pr, - (CH2) 2-c-Pr, cyclobutyl, (hereinafter in the present in addition "c-Bu"), CH2-c-Bu, (CH2) 2-c-Bu, oxyranyl, oxiranyl methyl or 2- (oxiranyl) -et-1-yl. The present invention also relates to processes for the preparation of compounds of the formula (I) or their salts, which comprises: a) reacting a compound of the formula (II) R1-Fu (II) where Fu is a group functional group selected from the group consisting of carboxylic ester, carboxylic orthoester, carboxylic acid chloride, carboxamide, carboxylic anhydride and trichloromethyl with a compound of the formula (III) or an acid addition salt thereof. b) reacting a compound of the formula (IV) where Z1 is an exchangeable radical or leaving group, for example chloro, trichloromethyl, alkylsulfonyl (C -? - C) and unsubstituted or substituted by phenyl- ^ &3 ^^^ ^ # «^ & ^^ & ^^^^^ * * ** - * * = i_ ^?. The alkyl sulfonyl (C? -C) or alkylphenylsulfonyl (C1-C4) with a suitable amine of the formula (V) or an acid addition salt thereof. wherein, in formulas (II), (III), (IV) and (V), the radicals R1, R2, R3, R4, A1, A2 and X and n are as defined in formula (I). The compounds of formulas (II) and (III) are preferably reacted with base catalysis in an inert organic solvent, such as, for example, tetrahydrofuran (THF), dioxane, acetonitrile, dimethylformamide (DMF), methanol and ethanol , at temperatures between -10 ° C and the boiling point of the solvent, preferably at 20 ° C to 60 ° C; if the acid addition salts of the formula (III) are used, they are, as a rule, released in situ with the aid of a base. Suitable bases or basic catalysts are alkali metal hydroxide, alkali metal hydrides, alkali metal carbonate, alkali metal alkoxide, alkali metal hydroxides, alkaline earth metal hydrides, alkaline earth metal carbonates or organic bases such as triethylamine or 1, 8-diazobicyclo [5.4.0] undec-7-ene (DBU). The base in question is used, for example, in the scale of 0.1 to 3 mol equivalents, based on the compound of the formula (III). The compound of the formula (III) can be used, for example, in equimolar amounts or in an excess of up to 2 mol equivalents, relative to the compound of the formula (III). The principles of the procedures in question are known from the literature (compare: Comprehensive Heterocyclic Chemistry, AR Katrizky, CW Rees, Pergamon Press, Oxford, New York, 1984, Vol.3, Part 2B, ISBN 0-08-030703 -5, p.290). The compounds of formulas (IV) and (V) are preferably reacted with base catalysis in an inert organic solvent such as, for example, THF, dioxane, acetonitrile, DMF, methanol and ethanol, at a temperature between -10. ° C and the boiling point of the solvent or the solvent mixture in question, preferably at 20 ° C to 60 ° C; if the compound (V) is used as an acid addition salt, it is, if appropriate, released in situ using a base. Suitable basic bases or catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alkoxide, alkali metal hydroxides, alkaline earth metal hydrides, alkaline earth metal carbonates or organic bases such as alkali metal hydroxides. triethylamine or 1,8-diazabicyclo [5.4.0] undec-7-ena (DBU). The base in question is used, as a rule, in the scale of 1 to 3 mol equivalents based on the compound of the formula (IV). The compound of the formula (IV) can be used, for example, in equimolar amounts relative to the compound of the formula (V) or in an excess of up to 2 mol equivalents. Principles 20 of the methods in question are known from the literature (see, Comprehensive Heterocyclic Chemistry, AR Katritzky, CW Rees, Pergamon Press, Oxford, New York, 1984, Vol. 3, Part 2B, ISBN 0-05-030703- 5, p 482).

- ^ .A ^^. ,. , - ^ .-,, - -. ^, .. ... - ..., .... . ^,, ¡. jaa.to ..

The starting materials of formulas (II), (III), (IV) and (V) are both commercially available, or can be prepared by, or analogous to, known methods of the literature. Some of the compounds of the formulas (III) and (V) are novel and are also subject to the invention. In addition, the compounds can be prepared, for example, by one of the methods described hereinafter. The compound of the formula (IV) or a direct precursor thereof can be prepared, for example, according to the following: 1. The reaction of a compound of the formula (II) with an amidinothiurea derivative of the formula SAW) wherein Z2 is alkyl (d-C) or phenyl-(C1-C4) alkyl and R3 is as defined in formula (I) which yields compounds of formula (IV) in which Z1 = -SZ2. 2. The reaction of an amidine of the formula (VII) or an acid addition salt of the same H2N-CR1 = NH (VII) where R1 is as defined in the formula (I) with an N-20 cyanodithioiminocarbonate of the formula (VIII) NC-N = C (S-Z3) 2 (VIII) wherein Z3 is alkyl (CrC4) or phenyl- (CrC) alkyl yielding compounds of the formula (IV) wherein Z1 = -S-Z3.

The reaction of an alkali metal dicyanamide with a carboxylic acid derived from the aforementioned formula (II) yields compounds of the formula (IV) wherein Z 1 = NH 2. 4. The reaction of trichloroacetonitrile with a nitrile of the formula (IX) R1-CN (IX) where R1 is as defined in the formula (I) yields, initially, compounds of the formula (X) R1 10 N ^ N ( X) where Z1 and Z4 are each CCI3, and these, when subsequently reacted with compounds of the formula H-R3 (R3 as in the formula (I)), leads to compounds of the formula (IV) wherein Z1 = CCI3. The carboxylic acid derivatives of the formula (II) are reacted with the amidinothiourea derivatives of the formula (VI) in an organic solvent such as, for example, acetone, THF, dioxane, acetonitrile, DMF, methanol, ethanol, at temperatures of -10 ° C to the boiling point of the solvent, preferably at 0 ° C to 20 ° C, preferably with base catalysis. However, the reaction can also be carried out in water or in mixtures of aqueous solvents with one or more of the aforementioned organic solvents. If (VI) is used as an acid addition salt, it can be released, if appropriate, in situ using a base. The bases or "*" "- ^ *» »" »» ~ »- '«,. . . ,. . . ».., - t,. "Itew. . -. ...,} . «** +,"? FF, ...,. ,. t.? , .t t ^ nm ^.

Suitable basic catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonate, alkali metal alkoxide, alkaline earth metal hydroxides, alkaline earth metal hydrides, alkaline earth metal carbonates or organic bases such as triethylamine or 1,8-diazaicyl [5.4.0] undec-7-ene (DBU). The base in question is used, for example, in the scale of 1 to 3 mol equivalents based on the compound of the formula (VI). For example, compounds of the formulas (II) and (VI) can be used in equimolar amounts or in an excess of up to 2 mol equivalents of the compound of the formula (II). The principles of the procedures in question are known from the literature (cf. H. Eilingsfeld, H. Scheuermann, Chem. Ber .: 1967, 100, 1874), the corresponding intermediates of the formula (IV) are novel. The amidines of the formula (VII) are reacted with N-cyanodithioiminocarbonates of the formula (VIII) in an inert organic solvent such as, for example, acetonitrile, DMF, dimethylacetamide (DMA), N-methylpyrrolidone (NMP), ethanol and ethanol, at a temperature of -10 ° C to the boiling point of the solvent, preferably at 20 ° C to 80 ° C, preferably with base catalysis. If (VII) is used as an acid addition salt, it can be released, if appropriate, in situ using a base. Suitable bases for basic catalysts are alkali metal hydroxide, alkali metal hydrides, alkali metal carbonates, alkali metal alkoxides, alkali metal hydroxides, alkali metal hydrides, alkaline earth metal carbonates or organic bases such as triethylamine or 1, 8- "» "" "* •" * "- diazabicyclo [5.4.0] undec-7-ene (DBU) The base in question is used, for example, on a scale of 1 to 3 mol equivalents based on the compound of In the formula (VIII), it is possible to use compounds of the formulas (VII) and (VIII), as a rule, in equimolar amounts or with an excess of 2 mol equivalents to the compound of the formula (VII). are known from the literature (see, TA Riley, WJ Henney, NK Dalley, BE Wilson, RK Robins, J. Heterocyclic Chem .: 1986, 23 (6), 1706-1714), the corresponding intermediates of the formula (IV) are novel The intermediates of the formula (X) wherein Z11 = chloro can be prepared by reacting alkali metal dicyanamide with a carboxylic acid derived from the formula (II), in which case Fu is preferably the functional group of carboxylic acid chloride or carboxamide The reactants are reacted, for example, with acid catalysis in an inert organic solvent such as, for example, toluene, chlorobenzene, chlorinated hydrocarbons at temperatures between -10 ° C and the boiling point of the solvent, preferably at 20 ° C to 80 ° C, it being possible that the intermediates formed which are going to be chlorinated in situ use an appropriate chlorinating reagent such as, for example, phosphoric oxychloride. Suitable acids are, for example, hydrohalic acids such as HCl or more Lewis acids, for example AICI3 or BF3 (cf. US-A-5095113, Du Pont). The intermediates of the formula (X) wherein Z Z 4 = trihalogenomethyl can be prepared by reacting the corresponding trihalogenacetonitriles with a carbonitrile of the formula (IX). The reactants are reacted, for example with acid catalysis in an inert organic solvent such as, for example, toluene, chlorobenzene, chlorinated hydrocarbons at temperatures between -40 ° C, and the boiling point of the solvent, preferably at -10 °. C at 30 ° C. Examples of suitable acids are hydrohalic acids such as HCl or the other Lewis acids such as, for example, AICI3 or BF3 (cf. EP-A-130939, Ciba Geigy). Intermediates of the formula (IV) wherein Z1 = alkylmercapto (d-C4) or unsubstituted phenyl- (C1-C4) alkyl mercapto can be converted with a suitable chlorinating reagent such as, for example, elemental chlorine or phosphoric oxychloride in an inert organic solvent such as, for example, toluene, chlorobenzene, chlorinated hydrocarbons or others at temperatures between -40 ° C and the boiling point of the solvent, preferably at 20 ° C to 80 ° C, to produce more reactive chlorotriazines of the formula (IV ) where Z1 = CI (see JK Chakrabarti, DE Tupper; Tetrahedron 1975, 31 (16), 1879-1882). Intermediaries of the formula (IV). wherein Z 1 = unsubstituted or substituted alkylmercapto (CC) or phenyl-alkylmercapto (C 1 -C 4) alkyl or alkylphenylthio (Cr C 4) can be oxidized with a suitable oxidation reagent such as, for example, m-chloroperbenzoic acid, hydrogen peroxide, potassium peroxomonosulfate in a suitable solvent such as, for example, chlorinated hydrocarbons, acetic acid, water, alcohols, acetone or mixtures thereof at temperatures between 0 ° C and the boiling point of the solvent, preferably 20 ° C to 80 ° C (see TA Riley, WJ Henney, NK ahfa ^ d-kttliMMaiuMiriiflÉi Dalley, B.E. Wilson, R.K. Robins; J. Heterocyclic Chem .; 1986, 23 (6), 1706-1714). Acids which are suitable for preparing the acid addition salts of the compounds of the formula (I) are the following: hydrohalic acids such as hydrochloric acid or bromohydric acid, in addition phosphoric acid, nitric acid, sulfuric acid, monocarboxylic acids or bifunctional and hydroxycarboxylic acids such as acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid or lactic acid and also sulfonic acids such as P-Toluenesulfonic acid or 1,5-naphthalenedisulfonic acid. The acid addition compounds of the formula (I) can be obtained in a simple manner by customary salt formation methods, for example by dissolving a compound of the formula (I) in a suitable organic solvent such as, for example, methanol, acetone, methylene chloride or benzine, and adding the acid at temperatures of 0 to 100 ° C, and can be isolated in known manner for example by filtration, and if appropriate, purified by washing with an inert organic solvent. The base addition salts of the compounds of the formula (I) are preferably prepared in inert polar solvents such as, for example, water, methanol or acetone at temperatures of 0 to 100 ° C. Examples of bases which are suitable for the preparation of the salts according to the invention are alkali metal carbonates such as potassium carbonate, alkali metal hydroxides and alkali metal hydroxides, for example ßuittM-ab ~ - "* - - *" ^ * • NaOH or KOH, alkali metal hydrides and alkaline earth metal hydrides, for example NaH, alkali metal alkoxides and alkaline earth metal alkoxides, for example sodium methoxide, potassium tert-butoxide, or ammonia or ethanolamine. For example, quaternary ammonium salts can be prepared by double decomposition or condensation with quaternary ammonium salts of the formula [NRR, R ,, R ,, + X- wherein R, R \ R "and Rm independently of one another are alkyl, phenyl or benzyl (C 1 -C 4) and X 'an anion, for example CI "or OH" The solvents referred to as "inert solvents" in the variants of the above process will be understood as meaning in each case of the solvents that are inert under the reaction conditions in question, but which do not need to be inert under any reaction conditions The compounds of the formula (I) according to the invention and their salts, all of which are defined hereinafter as compounds of the formula (I) (according to the invention), both monocotyledonous and dicotyledonous plants, which are important economically harmful plants, have an excellent herbicidal activity on both a broad spectrum. efficiently in perennial seeds that produce shoots of rhizomes, fragments of root graft or other perennial organs and that are difficult to control. In this context, it is not important if the substance is applied before planting, prior to prominence or after prominence. Specifically, representative examples of weed flora can be mentioned ^^. ^ ^ '^' Monocot and dicot that can be controlled by the compounds according to the invention, without the enumeration restriction to certain species. Examples of seed species in which the active substance acts efficiently are, among the monocotyledons, Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and also Cyperus species of the annual sector and among the perennial Agropyron species, Cynodon, Imperata and Sorgo, and also perennial Cyperus species. In the case of dicotyledonous seed species, the spectrum of The action extends to such species as, for example, Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomeae Matricaria, Abutilon and Aids among others, and Convolvulus, Cirsium, Rumex and Artemisia in the case of perennial seeds. The active substances according to the invention also have an outstanding seed control effect that occurs under specific conditions in the growth of rice, for example, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus. If the compounds according to the invention are applied to the surface of the soil before germination, then it is also prevented that the weed seedlings emerge completely, or that the weed grows until it has reached the cotyledon stage, but then its growth stops, and eventually after three to four weeks have elapsed they die completely.

"If the active substances are applied post-prominence to the green parts of the plants, the growth also stops drastically in a very short time after the treatment and the weed plants remain in a growth stage at the same time. point of the moment of application, or 5 die completely after a certain time, so that in this way, the competition of the weeds, which is harmful to the crop plants, is eliminated at a very early and sustained moment. Although the compounds according to the invention have an excellent herbicidal activity against monocotyledonous and dicotyledonous seeds, the crop plants of economically important crops, such as for example; wheat, barley, rye, rice, corn, beet, cotton and soybeans, are not completely damaged, or only to an insignificant degree. For these reasons, the compounds of the present invention are very suitable for selectively controlling the induced growth of plants in crops for agricultural use, even in ornamental plants. In addition, the substances according to the invention have excellent growth regulating properties in crop plants. They are involved in the metabolism of the plant on a regular basis and therefore can be used for the directed control of the constituent of the plant and to facilitate its harvesting, such as, for example, causing drying and atrophied growth. Furthermore, they are also very suitable for regulating and inhibiting generally the undesired vegetative growth, without simultaneously destroying the plants. The inhibition of vegetative growth acts in ^^^^ t i ^ mii ^^? ? ^?. ^^ tt ^^^^? ^ ^ t ^ m ?? t? ^ mkM? l-m t ili jlitUÉa ?? -? ? ? ?? i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i I II. Due to their regulatory properties of plant growth and herbicides, the active substances can also be used to control harmful plants in crops of known genetically modified plants, or genetically modified plants that are to be developed. As a rule, transgenic plants are distinguished by their particular convenient properties, for example by resistance to certain pesticides, mainly certain herbicides, resistance to diseases in plants or pathogens of plant diseases, such as certain insects or microorganisms such as fungi. , bacteria or viruses. Other particular properties refer, for example, to the harvested materials in relation to quantity, quality and storage properties, to the composition and specific constituents. Therefore, transgenic plants are known where the starch content is increased or the amount of the starch is altered or those where the harvested material has a different fatty acid spectrum. The compounds of the formula (I) according to the invention or their salts are preferably used in economically important transgenic crops of useful and ornamental plants, for example cereals such as wheat, barley, rye, oats, sorghum and millet, rice, yucca and corn, and other crops of beet, cotton, soybeans, oilseed rapeseed, potatoes, tomatoes, peas and other vegetables. The compounds of the formula (I) can preferably be used as herbicides in crops of useful plants which are resistant to the phytotoxic effects of the herbicides or which have thus been produced by genetic engineering. The additional ways of generating novel plants that have modified characteristics compared to existing plants consist of, for example in traditional breeding methods and the generation of mutants. However, it is also possible to generate novel plants with altered characteristics with the aid of genetic engineering methods (see, for example EP-A-0221044, EP-A-0131624). For example, various cases of genetic engineering modifications of crop plants have been described for the purpose of modifying the starch synthesized in the plants (for example WO 92/11376, WO 92/14827, WO91 / 19806), - plants of transgenic crops that are resistant to certain glufosinate-type herbicides (see, for example, EP-A-0242236, EP-A-242246) or of type (WO 92/00377) or of the sulfonylurea type and (EP-A-0257993, EU) -A-5013659), - plants of transgenic crops, for example cotton, which have the capacity to produce toxins of Bacillus thuringiensis (Bt toxins) The plant that makes the plants resistant to certain pesticides (EP-A-0142924, EP-A-0193259), - plants of transgenic crops whose fatty acid spectrum is modified (WO 91/13972). In principle, a large number of techniques in molecular biology are known by means of which novel transgenic plants with altered characteristics can be general, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY: or Winnacker "Gene und KIone" [Genes and Clones], VCH Weinheim 2a. 1996 Edition, or Christou, "Trends in Plant Science" 1 (1996) 423-431). To develop such genetic manipulations, the nucleic acid molecules can be introduced into plasmids that allow mutagenesis or a sequence change through the recombination of DNA sequences. It is possible, for example, with the help of the above mentioned standard methods, to develop base exchanges, to remove subsequences or to add natural or synthetic sequences. To connect the DNA fragments together, adapters or linkers can be attached to the fragments. For example, plant cells with reduced activity of a gene product can be generated by expressing at least one corresponding antisense RNA, a sense RNA to achieve a co-suppressive effect or by the expression of at least one ribozyme of suitable construction which specifically cuts the transcripts of the aforementioned gene product. For this purpose, it is possible to use, on the one hand, DNA molecules comprising the entire coding sequence of a gene product that includes any flanking sequence that may be present, on the other hand, DNA molecules that only comprise parts of the coding sequence, but these parts must be long enough to be able to effect an antisense effect on the cells. DNA sequences that show a high degree of homology with the coding sequences of a gene product, but which are not completely identical, can also be used. When the nucleic acid molecules are expressed in plants, the protein that has been synthesized can be located in any desired compartment of the plant cell. However, to achieve location in a particular compartment, it is possible, for example, to bind the coding region with DNA sequences that guarantee location in a particular compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227, Wolter et al., Proc. Nati. Acad. Sci. USA 85 (1988 ), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). The cells of transgenic plants can be regenerated by known techniques to give whole plants. In principle, the transgenic plants can be plants of any desired plant species, ie monocotyledonous and also dicotyledonous plants. This makes it possible to obtain transgenic plants that exhibit altered characteristics by overexpression, suppression or inhibition of homologous genes (= natural) or gene sequences or by expression of heterologous genes (= introduced) or gene sequences. The compounds (I) according to the invention can preferably be used in transgenic crops which are resistant to herbicides of the group of sulfonylureas, glufosinate-arnonium or glyphosate-isopropylammonium and analogous active substances. When the active substances according to the invention are used in transgenic crops, effects other than the herbicidal effects that will be observed in other crops are frequently found to be specific for application in the particular transgenic crop, for example an altered weed spectrum or specifically extended that can be controlled, altered application rates that can be used for application, preferably good combination ability with the herbicides to which the transgenic crop is resistant, and an effect on the growth and production of transgenic crop plants. Therefore, the invention also relates to the use of compounds (I) according to the invention as herbicides to control harmful plants in transgenic crop plants.

The use according to the invention for controlling harmful plants or for regulating the growth of plants also includes the case where the active substance of the formula (I) or a salt thereof is only formed in a plant or in the soil at starting from a precursor ("prodrug") after its application in the plant. The compounds according to the invention can be used in conventional preparations such as wettable powders, emulsifiable concentrates, sprayable solutions, powders or granules. Therefore, the invention also relates to herbicidal and plant growth regulating compositions comprising compounds of the formula (I) The compounds of the formula (I) can be formulated in various ways, depending on the prevailing biological and / or chemical-physical parameters. Examples of possible formulations that are suitable are: wettable powders (WP), water soluble powders (SP), water soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil in water and water emulsions in oil, sprayable solutions, suspension concentrates (SC), oil or water-based dispersions, solutions that are miscible with oil, capsule suspensions (CS), powders (DP), seed wrapping products, granules for soil application or for spreading, granules (GR) in the form of microgranules, spray granules, coated granules and adsorption granules, water dispersible granules (WG), water soluble granules (SG), ULV formulations, microcapsules and waxes.

The individual types of formulation are known in principle and are described, for example, in: Winnacker-Küchler, "Chemische Technologie" [Chemical Technology], Vol. 7, Editorial C. Hauser, Munich, 4th edition 1986; Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker N.Y., 1973; K. 5 Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London. Also known are the auxiliary formulation materials that are required, such as inert materials, surfactants, solvents and other additives, and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers," 2a. Ed., Darland Books, Caldwell N.J .; H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2a. Ed., J. Wiley & Sons, N.Y .; C. Marsden, "Solvents Guide", 2a. Ed., Interscience, N.Y. 1950; McCutcheon's, "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, "Grenzfláchenaktive Alyylenoxidaddukte "[Ethylene oxide surfactant adducts], Wiss. Verlagsgesell., Stuttgart 1997, W'nnacker-Küchler," Chemische Technologie "[Chemical technology], Volume 7, Editorial C. Hauser Verlag, Munich, 4th Ed. 1986. Based on these formulations, it is also possible to prepare combinations with other pesticidally active substances, such as, for example, insecticides, acaricides, herbicides, fungicides, and with insurers, fertilizers and / or growth regulators, for example in the form of rapid mixing or tank mixing.

Wettable powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, comprise ionic or nonionic surfactants (wetting agents, dispersants), for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, ether sulfates polyglycolics of fatty alcohol, alkanesulfonates or alkylbenzene sulphonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-d-sulphonate, sodium dibutylnaphthalene sulfonate or in its place sodium oleoylmethyltaurinate, in addition to a diluent or an inert substance . To prepare the wettable powders, the herbicidal active substances are, for example, finely milled in conventional apparatuses such as hammer mills, blower mills and air jet mills and mixed with the auxiliary formulation ingredients., either concomitantly or later. The emulsifiable concentrates are prepared, for example, by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene J instead aromatics or higher boiling hydrocarbons or mixtures thereof, with the addition of one or more agents ionic or nonionic surfactants (emulsifiers). Some examples of emulsifiers that can be used are: calcium salts of alkylarylsulfonic acids, such as calcium dodecylbenzenesulfonate or nonionic emulsifiers, such as polyglycol fatty acid esters, alkylaryl polyglycol ethers, polyglycol fatty alcohol ethers, propylene / ethylene oxide, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or polyoxyethylene sorbitan fatty esters such as polyoxyethylene sorbitan fatty acid esters. Powders are obtained by grinding the active substance with finally divided solid materials, for example talc or natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. The suspension concentrates may be water or oil based. They can be prepared, for example, by wet milling by commercially available sphere mills, if appropriate with the addition of surfactants, as already mentioned above, for example in the case of the other types of formulation. Emulsions, for example oil-in-water (EW) emulsions, can be prepared by stirrers, colloid mills and / or static mixtures using aqueous organic solvents and, if appropriate, surfactants as already mentioned above, for example in the case of the other types of formulation. Granules can be prepared either by spraying the active substance on the inert granulated adsorbent material or by applying it on the surface of carriers, such as sand, kaolinites or granulated inert material, with the aid of binders, for example polyvinyl alcohol, sodium polyacrylate or instead mineral oils. The appropriate active substances can also be granulated in the usual manner for ^ g ^^ and &^^^^^ preparation of fertilizer granules, if desired as a mixture with fertilizers. Water-dispersible granules are generally prepared by traditional methods such as spray drying, fluidized bed granules, disk granulation, mixing using high speed mixers and extrusion without solid inert material. For preparing discs, fluidized beds, extruders and spray granules, see for example, "Spray-Drying Handbook" procedures 3rd edition 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 et seq .; "Perry's Chemical Engineer's Handbook", 5th edition, McGraw-Hill, New York 1973, p. 8-57. For more details on the formulation of crop protection products, see, for example, G.C. Klingman, "Weed control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D.

Freyer, S.A. Evans, "Weed Control Handbook," 5th edition, Blackwell Scientific Publications, Oxford, 1968, pages 101-103. The agrochemical preparations generally comprise from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of active substance of the formula (I). In wettable powders, the concentration of active substance is, for example, approximately 10 to 90% by weight, the remainder being 100% by weight of customary formulation components. In the case of emulsifiable concentrates, the concentration of active substance can be from 1 to 90%, preferably from 5 to 80% by weight. The The formulations in the form of powders comprise in most cases from 1 to 30% by weight of the active substance, preferably from 5 to 20% by weight, solutions which can be sprayed at approximately 0.05% by weight. to 80%, preferably 2 to 50% by weight of the active substance. In the case of water-dispersible granules, the content of active substance depends in part if the active compound is in liquid or solid form and in which granulation auxiliaries and fillers are used. The granules dispersible in water, for example, comprise between 1 and 95% by weight of active substance, preferably between 10 and 80% by weight. In addition, the aforementioned active substance formulations include, if appropriate, adhesives, wetting agents, dispersants, emulsifiers, penetrating agents, preservatives, antifreeze agents, solvents, fillers, colorants, carriers, antifoams, evaporation inhibitors and pH regulators or viscosity that are usual in each case. The active substances that can be used as corr or components in mixed formulations or in a tank mixture, together with the active substances according to the invention, are, for example, known active substances as described in, for example, Weed Research 26, 441-445 (1986), or "The Pesticide Manual," 10th edition, The British Crop Protection Council and the Royal Soc. Of Chemistry, 1994 and the literature cited therein. The herbicides known from the literature and which can be combined with the compounds of the formula (I) are, for example, __ »___ ___ ___ __ __ __ __ __ __ __ __ __ __ __ __ __ __ __ __ following active substances (note: compounds are designated by the" common name "of the International Organization for Standardization (ISO) or by the chemical name, if appropriate, together with a usual code): 5 acetochlor; acifluorfen; Aclonifen; AKH 7088, ie [[[1- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidene] amino] oxy] acetic acid and its methyl ester; alachlor aloxydim; ametrin; amidosulfuron; Amitrol; AMS, i.e. ammonium sulphamate; anilophos; asulam; atrazine; azimsulfuron (DPX-A8947); aziprotrin; barban BAS 516 H, 10 i.e. 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; benazolin; benfluralin; benfuresate; bensulfuron-methyl; bensulide; bentazone; benzofenap; benzofluor; benzoylprop-ethyl; benzthiazuron; bialaphos; bifenox; bromacil; bromobutide; bromophenoxy; Bromoxynil; bromuron; buminafos; Busoxinone; butachlor; butamiphos; butenachlor; butidazole; butralin; butylate; cafenstrole (CH-900); 15 carbetamide; Cafentrazone (ICI-A0051); CDAA, i.e. 2-chloro-N, N-di-2-propenyl acetamide; CDEC, i.e. 2-chloroalyl diethyldithiocarbamate; clometoxifen; chloramben; clorazifop-butyl, chlormesulon (ICI-A0051); chlorbromuron; chlorbufam; chlorfenac; chlorflurecol-methyl; chloridazon; ethyl chlorimuron; clornitrofen; Chlorotoluron; chloroxuron; chlorprofam; Clorsulfuron; chlortal-dimethyl; 20 clortiamide; cinmetilin; Cinosulfuron; Cletodim; clodinafop and its ester derivatives (for example clodinafop-propargyl); clomazon; clomeprop; cloproxydim; clopyralid; cumiluron (JC 940); cyanazine; cycloate; cyclosulfamuron (AC 104); cycloxydim; cycluron; cyhalofop and its ester derivatives (for example ester butyl, DEH-112); cyperquat; ciprazine; ciprazole; daimuron; 2,4-DB; dalapon; desmedifam; desmethrin; di-alato; dicamba; diclobenil; dichlorprop; diclofop and its esters such as diclofop-methyl; dietyl; diphenoxuron; difenzoquat; diflufenican; dimefuron; dimethachlor; dimethamethrin; dimethenamid (SAN-582H); dimethasone, clomazon; dimetipin; dimethrulphuron, dinitramine; dinoseb; dinoterb; diphenamid; dipropetrin; diquat; ditiopir; diuron; DNOC; eglinazin-ethyl; EL 77, i.e. 5-cyano-1- (1,1-dimethylethyl) -N-methyl-1 H-pyrazole-4-carboxamide; endotal; EPTC; esprocarb; etalfluralin; etametsulfuron-methyl; etidimuron; etiozine; ethofumesate; F5231, i.e. N- [2-chloro-4-fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo-1 H-tetrazol-1-yl] -phenyl] ethanesulfonamide; ethoxyfen and their esters (for example ethyl ester, HN-252); etobenzanid (HW 52); fenoprop; fenoxan, fenoxaprop and fenoxaprop-P and their esters, for example fenoxaprop-P-ethyl and fenoxaprop-ethyl; phenoxydim; fenuron; flamprop-methyl; flazasulfuron; fluazifop and fluazifop-P and their esters, for example fluazifop-butyl and fluazifop-P-butyl; flucloralin; flumetsulam; flumeturon; flumiclorac and its esters (for example pentylester, S-23031); flumioxazin (S-482); flumipropin; flupoxam (KNW-739); fluorodifen; fluoroglycofen-ethyl; flupropacil (UBIC-4243); fluridone; flurocloridone; fluroxypyr; flurtamone; fomesafen; fosamine; furiloxifen; glufosinate; glyphosate; halosafen; halosulfuron and its esters (for example methyl ester, NC-319); haloxifop and its esters; haloxifop-P (= R-haloxifop) and its esters; hexazinone; imazametabenz-methyl; imazapyr; imazaquin and salts such as ammonium salt; imazetametapir; imazethapyr; imazosulfuron; ioxinil; isocarbamide; isopropalin; isoproturon; isouron; isoxaben; isoxapirifop; karbutylate; lactofen; lenacil; linuron; MCPA; MCPB; mecoprop; mefenacet; mefluidid; metamitron; metazachlor; metabenzthiazuron; metam; metazole; methoxyphenone; methyldimron; metabenzuron, methobenzuron; metobromuron; metolachlor; metosulam (XRD 511); methoxuron; metribuzin; metsulfuron-methyl; MH; molinate; monalid; monocarbamide dihydrogensulfate; monolinuron; monuron; MT 128, ie 6-chloro-N- (3-chloro-2-propenyl) -5-methyl-N-phenyl-3-pyridazinamine; MT 5950, i.e. N- [3-chloro-4- (1-methylethyl) phenyl] -2-methylpentanamide; naproanilide; napropamide; naptalam; NC 310, i.e. 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxy pyrazole; neburon; nicosulfuron; nipiraclofen; nitralin; nitrophen; nitrofluorfen; norflurazon; orbencarb; orizalin; Oxadiargyl (RP-020630); oxadiazon; oxyfluorfen; paraquat; pebble pendimetalin; perfluidone; fenisofam; fenmedifam; picloram; piperophos; pyributicarb; pirifenop-butyl; pretilachlor; primisulfuron-methyl; procyanine; prodiamine; profluralin; progiinazin-ethyl; promised prometrin; propachlor; propanil; propaquizafop and its esters; propazine; profam; propisoclor; propyl amide; prosulfalin; prosulfocarb; prosulfuron (CGA-152005); prinaclor; pyrazolinate; pirazon; pyrosulfuron-ethyl; pirazoxifen; pyridate; piritiobac (KIH-2031); piroxofop and its esters (for example propargyl ester); quinclorac; quinmerac; quinofop and its ester derivatives, quizalofop and quizalofop-P and their ester derivatives, for example quizalofop-ethyl; quizalofop-P-tefuril and -ethyl; renriduron; rimsulfuron (DPX-E 9636); S 275, i.e. 2- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -4,5,6,7-tetrahydro-2H-indazole; secbumeton; Sethoxydim; siduron; simazine; symmetry; SN 106279, ie 2 - [[7- [2-chloro-4- (trifluoromethyl) phenoxy] -2-naphthalenyl] oxy] propane and its methyl ester; sulfentrazon (FMC-97285, F-6285); sulfazuron; sulfometuron-methyl; Sulfosate (ICI-A0224); TCA; tebutam (GCP-5544); tebutiuron; terbacil; terbucarb; terbuclor; terbumeton; terbuthylazine; terbutrin; TFH 450, ie 5 N, N-diethyl-3 - [(2-ethyl-6-methylphenyl) sulfonyl] -1H-1, 2,4-triazole-1-carboxamide; Tenilchlor (NSK-850); thiazafluron; tizopir (Mon-13200); tidiazimin (SN-24085); tifensulfuron-methyl; thiobencarb; thiocarbazil; tralkoxidim; tri-alato; triasulfuron; triazophenamide; tribenuron-methyl; triclopyr; tridifan; trietazine; trifluralin; triflusulfuron and esters (for example methyl ester, DPX-66037); trimeturon; 10 tsitodef; vernolate; WL 110547, i.e. 5-phenoxy-1- [3- (trifluoromethyl) phenyl] -1 H-tetrazole; UBH-509; D-489; LS 82-556; KPP-300; NC-324; NC-330; KH-218; DPX-N8189; SC-0774; DOWCO-535; DK-8910; V-53482; PP-600; MBH-001; KIH-9201; ET-751; KIH-6127 and KIH-2023. For use, the formulations that are presented in commercially available form are, if appropriate, traditionally diluted, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water dispersible granules. Preparations in the form of powders, granules for application in soil, granules for spreading and conventionally sprayable solutions are no longer diluted with other inert substances before use. The required application rate of the compounds of the formula (I) varies with external conditions such as, among others, temperature, humidity and the nature of the herbicide used. It can vary within limits broad, for example between 0.001 and 10.0 kg / ha or more of active substance, but preferably between 0.005 and 5 kg / ha. The amounts (also percentages) in the following examples are based on weight, unless otherwise specified.

A. Chemical examples EXAMPLE A1 2-Amino-4- (1-fluoro-1-methyl-ethyl) -6- (3-phenyl-1-cyclobutyl-1-propylamino, 3,5-triazine (see Table 4, Example 4-2) A prepared solution of 0.32 g (0.014 mol) of sodium and 10 ml of methanol is added to 1.90 g (0.00613 mol) of 3-phenyl-1-cyclobutyl-1- (biguanidino) propane hydrochloride in 30 ml of methanol and 2 g of molecular sieve 3 A (Angróm). Then, 1.10 g (0.0092 mol) of methyl 1-f, uoro-1-methylpropionate are added by dropping and the mixture is stirred first for 2 hours at 25 ° C and then for 4 hours at 65 ° C. The reaction mixture is filtered, the filtrate is concentrated and the residue is taken up in ethyl acetate. The mixture is washed with water and dried with sodium sulfate. The desiccant is filtered with suction and the solvent is evaporated in vacuo. After purification by column chromatography (eluent: ethyl acetate), 1.66 g (79% theory) of 2-amino-4- (1-fluoro-1-methylethyl) -6- (3-phenyl-1) are obtained. -cyclobutyl-1-propylamino) -1, 3,5-triazine.

EXAMPLE A2 2-Amino-4- (1-fluoro-1-methyl-ethyl) -6- (1-phenyl-4-cyclopropyl-4-butylamino) -1.3.5-triazine (see example 22-12, table 22) 1.52 g (0.008 mole) of 2-amino-4-chloro-6- (1-fluoro-1-methylethyl) -1, 3,5-triazine and 1.64 g (0.012 mole) of potassium carbonate are introduced in 30 g. ml of acetonitrile. 1.50 g (0.008 mol) of 4-phenyl-1-cyclopropyl-1-butylamine, dissolved in 10 ml of acetonitrile, are added dropwise to this solution. The mixture is refluxed for three hours. The solid components are filtered with suction and the filtrate is evaporated in a rotary evaporator. The residue is purified by column chromatography (eluent: methyl acetate). This gives 2.36 g (86% theory) of 2-amino-4- (1-fluoro-1-methylethyl) -6- (1- phenyl-4-cyclopropyl-4-butylamino) -1, 3,5-triazine .

EXAMPLE A3 2 -Amin -4- (1-fluoro-1-methyl-ethyl) -6-f3- (3,5-dimethylphenyl) -1-cyclopropyl-1-propylamino-1,3,5-triazine (see Table 9, examples 9-17) A methoxide solution prepared from 1.2 g (0.05) moles) of sodium and 100 ml of methanol is added to 8.1 g (0.025 moles) of 3- (3,5-dimethylphenyl) -1-cyclopropyl-1- (1-biguanidino) propane hydrochloride in 50 ml of methanol and 7 g of molecular sieve ground 3Á. Then, 5.4 g (0.45 moles) of methyl 1-fluoro-1-methylpropionate are added and the mixture is stirred for 2 hours at 25 ° C and then for 4 hours at 65 ° C. The reaction mixture is filtered, the filtrate is concentrated and the residue is taken up in ethyl acetate. The mixture is washed with water and dried with sodium sulfate. The desiccant is filtered and the solvent is evaporated in vacuo. After purification by column chromatography (eluent: ethyl acetate), 7.4 g (83% theory) of 2-amino-4- (1-fluoro-1-fluoro-1-methylethyl) -6- [3 are obtained - (3,5-dimethyl) -1-cyclo-propyl-1-propylamino) -1, 3,5-triazine.

EXAMPLE A4 2-Amino-6-methyl-4-r3- (3-methylphenyl) -1-cyclobutyl-1-propylaminol-1, 3,5-triazine (see Table 4, Example 4-29) 2. 2 g (0.015 mol) of 2-amino-4-chloro-6-methyl-1, 3,5-triazine and 4.1 g. (0.03 moles) of K2CO3 are introduced into 50 ml of acetonitrile. 2.5 g (0.15 mol) of 3- (3-methylphenyl) -1-cyclobutyl-1-propylamine, dissolved in 20 ml of acetonitrile, are added dropwise to this solution. The mixture is refluxed for 3 hours. The solid constituents are subsequently filtered off with suction and the filtrate is evaporated on a rotary evaporator. The residue is purified by column chromatography (eluent: ethyl acetate). This gives 4.3 g (92% theory) of 2-amino-6-methyl-4- [3- (3-methylphenyl) -1-cyclobutyl-1-propylamino] -1,3,5-triazine. ^^ b ^ EXAMPLE A5 2-Amino-4- (1-fluoro-1-methyl-ethyl) -6-r4- (3,5-dimethyl-phenyl) -1-cyclopropyl-1-butylamino-1, 3, 5-triazine (see table 22. example 22-28) A methoxide solution prepared from 1.2 g (0.05 mole) of sodium and 100 ml of methanol is added to 8.4 g (0.025 mole) of 4- (3,5-dimethylphenyl) -1-cyclopropyl-1- ( 1-biguanidino) butane in 50 ml of methanol and 7 g of molecular sieve ground 3Á. Then 5.4 g (0.045 moles) of methyl 1-fluoro-1-methylpropionate are added and the mixture is stirred for 2 hours at 25 ° C and then for 4 hours at 65 ° C. The reaction mixture is filtered, the filtrate is concentrated and the residue is taken up in ethyl acetate. The mixture is washed with water and dried with sodium sulfate. The desiccant is filtered and the solvent is evaporated in vacuo. After purification by column chromatography (eluent: ethyl acetate), 7.7 g (83% theory) of 2-amino-4- (1-fluoro-1-fluoro-1-methylethyl) -6-3- are obtained. (3,5-dimethyl) -1-cyclopropyl-1-butylamino] -1, 3,5-tr jzine. The compounds described in the following tables 1 to 44 are obtained by or analogously to the above examples A1 to A5 or by the methods described above in general terms. The abbreviations in the tables mean: Me = methyl Et = ethyl Pr = propyl i-Pr = isopropyl c-Pr = cyclopropyl c-Bu = cyclobutyl t-Bu = tertiary butyl c-Hexyl = cyclohexyl A1 (CH,)! = -CH2- A2 = (CH2) 2 = -CH2CH2- A3 = (CH2) 3 = -CH CH CH2- A4 = (CH2) 4 = -CH2CH2CH2CH2 'Ac = COCH3 = acetyl O Ox = oxyranyl Ph = phenyl (X) n = "-" means r? = 0 The following tables 1 to 41 are related to the formula (1) H ^ M ^ aMM ^ MHbMi.

TABLE 1 TABLE 2 TABLE 3 H > _ < ^ -U ^ _Ü.

TABLE 4 TABLE 5 TABLE 6 10 fifteen twenty - - - - - * "« _ ^ Hi¿- ^ J, TABLE 7 TABLE 8 TABLE 9 ^^^ M ^^^^ Mi ^ ^^ WHM ^^ ÉHIttk lMaB ^ MMl * HaatB ^ MM TABLE 10 - - * - * r * -'- > - TABLE 11 TABLE 12 TABLE 13 TABLE 14 TABLE 15 TABLE 16 fifteen TABLE 17 twenty ^^ t ^ üaiaÉHmnat ^^ a ^ a a ^? ^ ?? t ^^^^^ TABLE 18 TABLE 19 w imtl ^ l ^ i? i ^ MÉükiH ^ -kgl-mi-iaÉÉ PICTURE 20 TABLE 21 ^ ¿HUH ^ i TABLE 22 TABLE 23 TABLE 24 TABLE 25 fifteen ^^^ TABLE 26 TABLE 27 TABLE 28 ^ üadiüMilMM TABLE 29 TABLE 30 wia mé a¡íiíi llí ^ TABLE 31 TABLE 32 15 20 - * »'• * - TABLE 33 15 TABLE 34 twenty riau? tt •: *** «- * < * »'TABLE 35 TABLE 36 fifteen üiHiál-áM-A ^ M ^^^^ ÉliMiMib TABLE 37 TABLE 38 Á ^ Édau ^ aAa-k. É ^^ m ^^^ ¿átll? lkít TABLE 39 TABLE 40 fifteen - * ••• * > - «-" - «=» -.. * ... - ^. «Ta» TABLE 41 j ^ i ^ ^^^^^^^^^^^^^^^^^^^^^^ 42 Compounds of the formula (2) 15 A? Jmu ^ íí a ^ TABLE 43 Compounds of the formula (3) TABLE 44 Compounds of the formula (4) (4) 10 20 NMR data for individual examples: at * MM > ÍWtMl --- ÉÜHÉaiH EXAMPLE 4-2 1 H NMR (DMSO-de): d = 1.5 (s, 3 H), 1.6 (s, 3 H), 1.5 - 2.0 (m), 2.4 - 2.6 (m), 4.0 (m, 1 H), 7.2 (m) , 5H) 5 EXAMPLE 4-28 1 H NMR (CDCl 3): 1.6 (s, 3 H), 1.7 (s, 3 H), 1.5 - 1.9 (m), 2.4 (m, 2 H), 2.6 - 2.7 (m, 2 H), 4.1 (m, 1 H) , 4.1 (m, 1 H), 6.8 - 7.0 (m, 3H), 7.2 (m, 1 H) 10 EXAMPLE 18-1 1 H NMR (DMSO-de): d = 1.5 (s, 3 H), 1.6 (s, 3 H), 1.7 - 2.1 (m, 2 H), 2.5 - 2.6 (m, 2 H), 5.0 (m, 1 H), 7.2 - 7.7 (m, 8H) 15 EXAMPLE 20-1 1 H NMR (CDCl 3): d = 1.5 (s, 3 H), 1.6 (s, 3 H), 1.6 - 2.4 (m, 5 H), 2.5 - 2.8 (m, 2 H), 3.6 - 3.9 (m, 4 H), 4.2 m (1 H), 7.2 m (5H) EXAMPLE 22-3 1 H NMR (DMSO-d 6): d = 0.1 (m, 1 H), 0.3 (m, 2 H), 0.4 (m, 1 H), 0.9 (m, 1 H), 1.5 (s, 3 H), 1.6 (s, 3 H) ), 3.5 m (1H), 7.1 - 7.3 (m, 5H) EXAMPLE 22-25 1 H NMR (CDCl 3): d = 0.2 - 0.6 (m, 4 H), 0.8 (m, 1 H), 1.2 (d, 6 H), 1.6-1.8 (m, 4 H), 2.5 - 2.7 (m, 2 H), 3.5 m (1H), 6.9 (m, 3H), 7.2 m (1H) EXAMPLE 28-10 1 H NMR (DMSO-de): d = 1.5 (s, 3H), 1.6 (s, 3H), 1.5-1.9 (m), 2.6 (m), 4.0 (m, 1H), (m, 1H), 7.1 - 7.3 m (5H) EXAMPLE 30-2 1 H NMR (CDCl 3): d = 0.2 - 0.6 m (4 H), 0.8 - 1.0 (m, 3 H), 1.4 m (2 H), 1.5 (s, 3 H), 1.7 (s, 3 H), 2.6 (t, 2 H) ), 3.5 (m, 1H), 7.1 - 7.3 (m, 5H) EXAMPLE 32-12 1 H NMR (DMSO-de): d = 0.1 (m, 2 H), 0.4 (m, 2 H), 0.7 m (1 H), 1.2 (d, 6 H), 1.4 (m, 3 H), 1.8 (m, 2 H) ), 2.5 - 2.7 m (2 H), 3.7 (m, 3 H), 4.0 (m, 1 H), 6.7 (m, 3 H), 7.2 m (1 H) EXAMPLE 33-3 1 H NMR (DMSO-de): d = 1.1 (d, 6H), 1.5-1.9 (m), 2.5-2.7 (m), 4.1 (m, 1 H), 7.1-7.3 (m, 5H) EXAMPLE 44-1 1 H NMR (DMSO): d = 0.2 - 0.6 (4H), 1.0 (m, 1 H), 1.5 (m, 3H), 1.6 (m, 3H), 4.1 (m, 1 H), 6.3 (dd, 1 H), 6.5 (d, 1 H), 7.2 - 7.4 (m, 5H) B. Formulation Examples a) A powder is obtained by mixing 10 parts by weight of a compound of the formula (I) and 90 parts by weight of talc as an inert material and grinding the mixture in a hammer mill. b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of a compound of the formula (I), 64 parts by weight of quartz containing kaolin as an inert material, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurinate as humectant and dispersant and grinding the mixture in an articulated disc mill. c) A dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of a compound of the formula (I) with 6 parts by weight of alkylphenol polyglycol ether (® Triton X 207), 3 parts by weight of ether polyglycol isotridecanol (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling scale for example about 255 to more than 277 ° C) and grinding the mixture in a ball mill to a fineness of less than 5 microns. d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I), 75 parts by weight of ciciohexanone as a solvent and 10 parts by weight of the oxethylated nonylphenol as an emulsifier. e) water-dispersible granules are obtained by mixing 75 parts by weight of a compound of the formula (I), 10 parts by weight of calcium lignosulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol and 7 parts by weight. parts by weight of kaolin, grinding the mixture in an articulated disc mill and granulating the powder in a fluidized bed by spraying on water as a granulation liquid. f) alternatively, the water-dispersible granules are obtained by homogenization and precominutation, in a colloidal mill, 25 parts by weight of a compound of the formula (I), 5 parts by weight of 2,2'-dinaphthylmethane-6 , 6'-sodium disulfonate, 2 parts by weight of sodium oleoylmethyltaurinate, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water, subsequently grinding the mixture in a dial mill and atomizing and drying the resulting suspension in a spray tower through a single substance nozzle.

C. Biological examples 1. Preemergence effect in weeds Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds are placed in sandy clay soil in plastic containers and covered with soil. The compounds according to the invention which are formulated in the form of wettable powders or emulsion concentrates are applied to the surface of the floor covering in the form of an aqueous suspension or emulsion at an application rate of 600 to 800 I of water. ha (converted), in different doses.

After treatment, the containers are placed in the greenhouse and kept under good growth conditions for the weeds. After the test plants have arisen, the damage to the plants or the negative effect on emergence is calculated visually after a trial period of 3 to 4 weeks compared to the untreated controls. As shown by the test results, the compounds according to the invention have a good herbicidal preemergence action against a wide variety of weeds and dicotyledonous weeds. For example, examples numbers 4-1, 4-2, 4-3, 4-10, 4-11, 4-14, 4-15, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 8-1, 8-2, 9-1, 9-2, 9-3, 9-4, 9-5, 9 -6, 9-7, 9-8, 9-9, 9-10, 9-11, 9-12, 9-13, 9-14, 9-15, 9-16, 9-17, 9-18 , 9-19, 10-1, 18-1, 18-2, 18-3, 18-4, 19-5, 19-6, 20-1, 20-2, 22-3, 22-6, 22 -8, 22-9, 22-1 1, 22-12, 22-18, 22-24, 22-25, 22-26, 22-27, 22-28, 22-29, 22-30, 33- 31, 28-4, 28-5, 28-10, 28-13, 28-14, 28-17, 28-18, 28-20, 28-21, 30-1, 30-2, 31-1, 31-2, 31-3, 32-1, 32-2, 32-5, 32-6, 32-9, 32-10, 32-11, 32-12, 33-2, 33-4, 44- 1 and 14-2 (see tables 1 to 44) show a very good herbicidal action in the test against harmful plants such as Stellaria media, Lolium multiflorum, Amaranthus retroflexus, Sinapis alba, Avena sativa and Setaria viridis when preemergence is applied at a rate of application of 1 kg or less of active substance per hectare. 2. Post-prevalence effect in weeds Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds are placed in sandy clay soil in plastic containers, covered with soil and grown in the greenhouse under good growing conditions. Three weeks after sowing, the test plants are treated in the three-leaf stage. The compounds according to the invention which are formulated as wettable powders or as emulsion concentrates are sprinkled in various doses on the green parts of the plants at an application rate of 600 to 800 I of water / ha (converted). After the test plants have remained in the greenhouse for approximately 3 to 4 weeks under ideal growth conditions, the effect of the preparations is calculated visually by comparison with the untreated controls. The agents according to the invention also have a good postemergence herbicidal action against a wide variety of economically important grass weeds and dicotyledonous weeds. For example, examples numbers 4-1, 4-2, 4-3, 4-10, 4-11, 4-14, 4-15, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 8-1, 8-2, 9-1, 9-2, 9-3, 9-4, 9-5, 9-6, 9-7, 9- 8, 9-9, 9-10, 9-11, 9-12, 9-13, 9-14, 9-15, 9-16, 9-17, 9-18, 9-19, 10-1, 18-1, 18-2, 18-3, 18-4, 19-5, 19-6, 20-1, 20-2, 22-3, 22-6, 22-8, 22-9, 22- 11, 22-12, 22-18, 22-24, 22-25, 22-26, 22-27, 22-28, 22-29, 22-30, 33-31, 28-4, 28-5, 28-10, 28-13, 28-14, 28-17, 28-18, 28-20, 28-21, 30-1, 30-2, 31-1, 31-2, 31-3, 32- 1, 32-2, 32-5, 32-6, 32-9, 32-10, 32-11, 32-12, 33-2, 33-4, 44-1 and 44-2 (see tables 1 to 43) show, in the test, a very good herbicidal action against harmful plants such as Sinapis alba, Echinochloa crus-galli, Lolium multiflorum, Stellaria media, Cyperus iría, Amaranthus retroflexus, Setaria viridis and Avena sativa when postemergence is applied at a high speed of application of 1 kg and less of active substance per hectare. 3. Effect on harmful plants in rice Planted and seeded rice and typical monocotyledonous and broadleaf rice weeds are grown in the greenhouse at the three-leaf stage (Echinochloa crus-galli 1.5 leaf) under paddy conditions (depth of water: 2 -3 cm) in sealed plastic containers. They are then treated with the compounds according to the invention. For this purpose, the formulated active substances are suspended, dissolved or emulsified in water and applied in various doses by pouring into water with which the test plants are flooded. After this treatment, the test plants 3 place in the greenhouse under ideal growth conditions and remain so throughout the experimental period. Approximately 3 weeks after the application, the test is evaluated by visual damage score to the plants compared to untreated controls. The compounds according to the invention have a very good herbicidal action against harmful plants. For example, the compounds of examples numbers 4-1, 4-2, 4-14.4-15, 4-23, 4-24, 9-4, 9-5, 9-9, 9-7 and 9 -10 (see tables 1 to 44) show, in the test, a very good herbicidal action against harmful plants which are typical for rice cultivation, such as, for example, Cyperus monti, Echinochola crus-galli and Sagittaria pygmaea. 4. Tolerance for crop plants In other greenhouse experiments, the seeds of a substantial number of crop plants and weeds are placed on sandy clay soil and covered with soil. Some of the containers are treated immediately as described in section 1, and the remaining containers are placed in a greenhouse until the plants have developed two to three true leaves and then sprinkled with various doses of the substances of the formula ( I) according to the invention, as described in section 2. Visual scoring is performed four or five weeks after application and after the plants have been in the greenhouse it is revealed that the compounds according to the invention do not cause no damage to dicotyledonous crops >; s such as, for example, soybean, rapeseed oil, beet and potatoes when pre- and postemergence are used, even when high doses of active substance are used. In addition, some substances also leave Gramineae crops unharmed, such as, for example, barley, wheat, rye, sip, corn or rice. Some of the compounds of the formula (I) have a high selectivity and are therefore suitable for controlling unwanted plant growth in agricultural crops.

Claims

NOVELTY OF THE INVENTION CLAIMS

1. - A compound of the formula (I) or a salt thereof wherein R1 is aryl which is unsubstituted or substituted, or (C3-Cg) cycloalkyl, which is unsubstituted or substituted, or heterocyclyl which is substituted or unsubstituted, or alkyl (Cr6), (C2-C6) alkenyl or alkynyl (C? -Ce), each of the last three mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, nitro, thiocyanate, alkoxy (C-> 4) , haloalkoxy (C2-C), alkenyloxy (C2-C4), haloalkenyloxy (C2-C4), alkylthio (C? -C4), alkylsulfinyl (C4), alkylsulfonyl (CrC4), haloalkylsulfinyl (C4), haloalkylsulfonyl (C) C4) and cycloalkyl (C3-Cg) which is unsubstituted or substituted, and phenyl which is unsubstituted or substituted and heterocyclyl which is unsubstituted or substituted, and radicals of the formulas R'-C (= Z ') -, R * -C (= Z ') - Z-, R, -ZC (= Z') -, R'R "NC (= Z ') -, R'-ZC (= Z') - O-, R ' R "NC (= Z,) - Z-, R'-ZC (= Z ') - NR" - and R, R "NC (= Z,) - NR", - in which R', R "and R "'in each case independently one of the other are alkyl MtfU ^ J.riMf ttMM (Ci-Cß), aryl, aryl- (C? -C6) alkyl, (C3-C9) cycloalkyl or (C3-C9) -alkyl (CrC6) cycloalkyl, each of the latter 5 radicals mentioned being substituted or unsubstituted, and wherein Z and Z 'independently of each other are in each case an oxygen or sulfur atom, R2 is cyclopropyl which is unsubstituted or substituted, cyclopentyl which is unsubstituted or substituted, cyclohexyl which is unsubstituted or substituted, cycloalkenyl (C-Cg), which is unsubstituted or substituted, or heterocyclyl which is substituted or unsubstituted, R3 is hydrogen, alkyl (Ci-Cß), aryl or cycloalkyl (O3-C9) , each of the last 3 mentioned radicals being substituted or unsubstituted, or a radical of the formula -N (B1-D1) (B2-D2) or -NR'-N (B1-D1) (B2-D2) in wherein B1, B2, D1 and D2 are in each case as defined below and R '= hydrogen, alkyl (Ci-Cß) or [alkyl (CrC6)] carbonyl, R4 is a radical of the formula -B3-D3, B3 and D3 being as they are defined post Accordingly, A1 is straight-chain alkylene having 1 to 5 carbon atoms or alkenylene or alkynylene, straight chain, each of which has 2 to 5 carbon atoms, each of the last three divalent radicals mentioned above. are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, cyano, thiocyanate and radicals of the formula B4-D4, B4 and D4 as defined below, A2 is a direct-bonding alkylene or straight chain having 1 to 4 carbon atoms or alkenylene or alkynylene, straight chain, each of which has 2 to 5 carbon atoms, each of the last three divalent radicals mentioned being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, cyano, thiocyanate and radicals of the formula -B5-D5 or a divalent radical of the formula V1, V2, V3, V4, or V5, -CR6R7-W * - CR8R9- (V1), -CR10R11-W * -CR12R13-CR14R1 5- (V2), -CR16R17-CR18R19-W * -CR20R21- (V3), -CR22R23-CR24R25-W * - (V4), -CR26R27-W * - (V5), each of the radicals R6 or R27 in each case independently of one another are hydrogen, halogen, nitro, cyano, thiocyanate or a radical of the formula -B6 -D6, W * is in each case an oxygen atom, a sulfur atom or a group of the formula N (B7-D7) and B5, B6, B7, D5 D6 and D7 are as defined below, B1, B2, B3 and B7 in each case independently of one another are a direct or divalent linking group of the formulas -C ( = Z *) -, -C (= Z *) - Z ** -, -C (= Z *) - NH- or -C (= Z *) - NR * -, Z * being an oxygen atom or sulfur, Z ** an oxygen or sulfur atom and R * alkyl (CrC6), aryl, aryl- (CrCe) alkyl, cycloalkyl (C3-Cg) or cycloalkyl (C3-Cg) -alkyl (C? -Ce), each of the last 5 mentioned radicals are unsubstituted or substituted, B4, B5 and B6 in each case independently of one another are a direct linking group or a divalent group of the formulas -O-, -S (O) p-, -S (O) pO-, -OS (O) p-, -CO-, -O-CO-, -CO-O-, S-CO-, -CO-S -, -S-CS-, -CS-S-, -O-CO-O-, -NR ° -, -O-NR0-, NR ° -0-, - NR ° -CO-, -CO-NR0 -, -O-CO-NR0- or - NR ° -CO-O-, p being the integer 0, 1, or 2 and R ° being hydrogen, alkyl (C? -C6), aryl, aryl- ( C? -Ce) alkyl, cycloalkyl (C3-Cg) or cycloalkyl (C3-C9) -alkyl (C? -Ce), each of the last 5 mentioned radicals are unsubstituted or substituted, D1, D2, D3, D4 , D5 and D6 in each case independently of one another are hydrogen, alkyl (C Cß), aryl, aryl- (C1-Ce) alkyl, cycloalkyl (C3-Cg) or cycloalkyl (C3-Cg) -alkyl (C? C6), it consists of halogen, nitrogen, cyano, (C4) alkyl, (C4) alkoxy, alkylthio (CrC), haloalkyl (C -? - C4), haloalkoxy (C-1-C4), formyl, alkylcarbonyl (C? C4) and alkoxycarbonyl (CrC4), or is (C3-C9) cycloalkyl, (C3-Cg) cycloalkylamino, (C3-Cg) cycloalkylamino, phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclicthio or heterocyclylamino, each of the last 11 mentioned radicals are unsubstituted or substituted, or two adjacent radicals X which together are a fused ring having from 4 to 6 ring atoms and is carbocyclic or containing ring heteroatoms selected from the group consisting of O, S and N and that is unsubstituted or substituted by one 10 or more radicals selected from the group consisting of halogen, alkyl (dC) and oxo, n is 0, 1, 3, 4 or 5, and heterocyclyl in the above-mentioned radicals independently of each other is in each case a heterocyclic radical which has from 3 to 7 ring atoms and 1 to 3 heteroatoms selected from the group consisting of N, O and S, wherein the total of 15 carbon atoms of the radicals A1 and A2-R2 add at least 6 carbon atoms.

2. A compound of the formula (I) or a salt thereof according to claim 1, wherein R1 is preferably phenyl which is unsubstituted or substituted by one or more radicals selected from the group 20 consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfo, cyano, thiocyanate, (C 1 -C 4) alkyl, haloalkyl (C 1 -C 4), alkoxy (C 1 -C 4), haloalkoxy (C 1 -C 4), (C 1 -C 4) alkylthio, haloalkylthio (C 1 -C 4), monoalkylamino (C 1 -C 4), dialkylamino (C 1 -C 4), cycloalkyl (C 3 -Cg), [alkyl (CrC 4)] carbonyl, [alkoxy (Cr Hil - WU ^ C4)] carbonyl, aminocarbonyl, monoalkylaminocarbonyl (C -? - C4), dialkylaminocarbonyl (C -? - C4), alkylsulfonyl (C C4) and haloalkylsulfonyl (Ci-C4), or cycloalkyl (C3-Cg) which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, cyano, thiocyanate, (C 1 -C 4) alkyl, haloalkyl (C C 4), (C 1 -C 4) alkoxy, haloalkoxy (C 1) -C4), alkylthio (C4), haloalkylthio (C4), monoalkylamino (C4), dialkylamino (CC) or heterocyclyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino , nitrogen, formyl, carboxyl, sulfonyl, cyano, thiocyanate, alkyl (CrC), haloalkyl (C1-C4), alkoxy (C1-C4), haloalkoxy (C1-C4), alkylthio (C1-C4), haloalkylthio (CC) , monoalkylamino (CrC4), dialkylamino (C -? - C4), cycloalkyl (C3-Cg), [alkyl (CrC4)] carbonyl, [alkoxy (CrC4)] carbonyl, aminocarbonyl, monoalkylaminocarbonyl (C1-C4), dialkylaminocarb onyl (d-C4), alkylsulfonyl (CrC4) and haloalkylsulfonyl (CrC4), or alkyl (Ci-Cß), alkenyl (C? -C) or alkynyl (C2-C6), each of the last 3 radicals mentioned are not substituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, nitrogen, thiocyanate, alkoxy (CC ^, haloalkoxy (C -? - C), alkenyloxy (C2-C), haloalkenyloxy (C2-C4) ), (C 1 -C 4) alkylthio, (C 1 -C 4) alkylsulfinyl, (C 2 -C 4) alkylsulfonyl, (C 1 -C 4) haloalkylsulfinyl, haloalkylsulfonyl (C 4 C) and (C 3 -C 6) cycloalkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, cyano, thiocyanate, alkyl (C? -C4), haloalkyl (C? -C), alkoxy (C1-C4), haloalkoxy (C1-C4), alkylthio (C1-C4), tf-EÉttnitaúáiH haloalquiltio (C1-C4), monoalkylamino (C1-C4) and dialkylamino (C1-C4) and phenyl and heterocyclyl, each of the last two mentioned radicals are not replaced or replaced by one or more radicals selected from the group that consists of halogen, hydroxyl, amino, nitrogen, formyl, carboxyl, sulfonyl, cyano, thiocyanate, alkyl (C4), haloalkyl (C4), alkoxy (CrC), haloalkoxy (CC), alkylthio (C1-C4), haloalkylthio (C C4), monoalkylamino (C C4), dialkylamino (C1-C4), (C3-Cg) cycloalkyl, [(CrC4) alkyl] carbonyl, [(C4) alkoxy] carbonyl, aminocarbonyl, monoalkylaminocarbonyl (CrC4), dialkylaminocarbonyl (C? -C4), alkylsulfonyl (CrC) and haloalkylsulfonyl (C? -C4), and radicals of the formulas R'-C (= Z) -, R'-C (= Z ') - Z-, R, -ZC (= Z') -, R * R "-C ( = Z ') -, R'-ZC (= Z') - O-, R'R "NC (= Z ') - Z-, R'-ZC (= Z') - NR" - and R, R "NC (= Z,) - NR-, in which R ', R" and R' "in each case independently of one another are (C 1 -C 4) alkyl, phenyl, (C 1 -C 4) alkylphenyl, (C 3) cycloalkyl -Cβ) or (C3-C6) cycloalkyl-alkyl (CrC4), each of the last 5 mentioned radicals are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, cyano, thiocyanate, (C1-C4) alkoxy, (C1-C4) alkylthio, (C1-C4) monoalkylamino, dialkylamino (C1-C4), alkenyl (C2-C4), alkynyl (C2-C4), cycloalkyl (C3- Ce) and in the case of cyclic radicals also alkyl (C? -C4) and haloalkyl (CC), and in which Z and Z 'independently of one another are in each case an oxygen or sulfur atom.

3. A compound of the formula (I) or a salt thereof according to claim 1 or 2, wherein R is cyclopropyl, > »-» -.- - "-» cyclobutyl, cyclopentyl or cyclohexyl, each of which is unsubstituted or substituted by one or more radicals selected from the group consisting of the radicals A), B), C) and D ), wherein group A) is composed of the radicals halogen, hydroxyl, amino, nitro, formyl, carboxyl, aminocarbonyl, sulfo, cyano, thiocyanate and oxo, group B) is composed of the alkyl radicals (C Cß), alkoxy (Ci-Cß), alkylthio (CI-CT), monoalkylamino (Ci-Cß), dialkylamino (C-1-C4), alkenyl (CrC6), alkynyl (C2-C6), cycloalkyl (C3-C9), cycloalkenyl (C4-Cg), alkylidene (C-Cß), cycloalkylidene (C4-Cg), radicals of the formulas R, -C (= Z ') -, R'-C (= Z') - ZC (= Z ') -, R'R "NC (= Z, R'-ZC (= Z ') - O-, R'R" NC (= Z') - Z-, R'-ZC (= Z '= - NR " - and R'R "NC (= Z ') - NR'" - wherein R ', R "and R'" in each case independently of one another are alkyl (Ci-Cß), phenyl, phenylalkyl (C C6) , cycloalkyl (C3-C9) or cycloalkyl (C3-Cg) -alkyl (CrC6) and where Z and Z 'independently Each other is in each case an oxygen or sulfur atom, group C) is composed of radicals as shown for group B), but each radical being substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfo, cyano, thiocyanate, alkoxy (CrC4), haloalkoxy (C1-C4), alkylthio (CrC4), haloalkylthio (C1-C4), monoalkylamino (CrC), dialkylamino (C1-C4) ), (C3-Cg) cycloalkylene, (C4-Cg) cycloalkylene, (C4-Cg) cycloalkylidene, [(CrC4) alkyl] carbonyl, [(C? -C4) alkoxy] carbonyl, aminocarbonyl, (C1-C4) monoalkylaminocarbonyl , dialkylaminocarbonyl (C 1 -C 4), phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio and heterocyclylamino, each of the last mentioned 21 radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, cyano, (C -? - C4) alkoxy, alkylthio (C4), haloalkoxy (C -? - C4), form ilo, alkylcarbonyl (C C4) and alkoxycarbonyl (CC), and in the case of cyclic radicals, in addition (C4) alkyl, haloalkyl (CrC4), and 5-alkylidene (Ci-Cß), and in the case of cyclic radicals furthermore , alkyl (C Cß), haloalkyl (CrC 6) and alkylidene (CrC 6), and group D) is composed of divalent or trivalent aliphatic bridges having from 1 to 6, preferably from 1 to 4, carbon atoms which, in the case of divalent bridges, two connect and in the case of trivalent bridges three carbon atoms of the The cyclic structure and the radical R2 therefore represents the radical of a bicyclo or tricycle, each of the bridges being unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, nitro, cyano, alkyl (C1-) C4), (C 1 -C 4) alkoxy, (C 1 -C 4) alkylthio, (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy, formyl, (C 1 -C 4) alkylcarbonyl, (C 1 -C 4) alkoxycarbonyl, and Oxo, or (C4-Cg) cycloalkenyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of the radicals A), B), C) and D) as defined as radicals for R2 = cycloalkyl (C3-Cg), or heterocyclyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of radicals A), B), C) and D) as they are 20 defined as radicals for R2 = cycloalkyl (C3-Cg).

4. A compound of the formula (I) or a salt thereof according to any of claims 1 to 3, wherein R3 is hydrogen, alkyl (C? -C4), which is unsubstituted or substituted by one or plus üba ^ radicals selected from the group consisting of halogen, hydroxyl, amino, cyano, thiocyanate, (C? -C4) alkoxy, haloalkoxy (CrC4), alkylthio (C1-C4), haloalkylthio (C? -C4), monoalkylamino (CC) ) and dialkylamino (CC), or phenyl or cycloalkyl (C3-C6), each of the last 2 mentioned radicals are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, carboxyl, sulfonyl, cyano, thiocyanate, alkyl (dC), haloalkyl (C1-C4), alkoxy (C -? - C4), haloalkoxy (C1-C4), alkylthio (CrC4), haloalkylthio (C1-C4) , monoalkylamino (C C4), dialkylamino (C? -C4), cycloalkyl (C3-C9), [alkyl (CrC)] carbonyl, [(C10C4) alkoxy] carbonyl, aminocarbonyl, monoalkylaminocarbonyl (C1-C4), dialkylaminocarbonyl (C1-C4), alkylsulfonyl (CrC) and haloalkylsulfonyl (Cr C4), or a radical of the formula N (B1-D1) (B2-D2), R4 is a radical of the formula -B3-D3, A1 is alkylene straight chain having 1 to 5 carbon atoms or straight chain alkenylene or alkynylene, each of which has 2 15 to 5 carbon atoms, each of the last three divalent radicals mentioned are substituted or unsubstituted by one or more radicals selected from the group consisting of halogen, nitrogen, cyano, thiocyanate and a radical of the formula -B4-D4 , B4 is a direct bond or a divalent group of the formulas -O-, -SO2-, -CO-, -O-CO-, -NR ° -, - NR ° -CO-, -CO- 20 NR ° - , -O-CO-NR0- or -NR ° -CO-O-, where R ° and D4 independently of each other are in each case hydrogen, (C 1 -C 4) alkyl, phenyl, phenylalkyl (CC), cycloalkyl (C 3) -C4) or cycloalkyl (C? -C4) -alkyl (CrC4), each of the last 5 radicals mentioned are substituted or unsubstituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, carboxyl, sulfonyl, cyano, thiocyanate, alkoxy (CrC), haloalkoxy (C? -C4), alkylthio (CrC4), haloalkylthio (C4), monoalkylamino (Ci- C4), dialkylamino (C 1 -C 4), cycloalkyl (C 3 -C 9), [(C 1 -C 4) alkyl] carbonyl, [alkoxy (CrC 4)] carbonyl, aminocarbonyl, monoalkylaminocarbonyl (C C 4), dialkylaminocarbonyl ( CC), alkylsulfonyl (C4), haloalkylsulfonyl (C4), and in the case of cyclic radicals in addition (C1-C4) alkyl and haloalkyl (C4), A2 is a direct bond or a group of the formula -CH2- , -CH2CH2-, - CH2CH2CH2-, - CH2CH2CH2CH2, each of the last 4 divalent radicals mentioned above are substituted or unsubstituted by one or more radicals selected from the group consisting of halogen, nitrogen, cyano, thiocyanate and radicals of the formula -B ^ -D5- or a divalent radical of the formula V1, V2, V3, V4 or V5, -CR6R7-W * -CR8R9- (V1), -CR10R11- W * -CR12R13-CR14R15- (V2), -CR16R17-CR18R19-W * -CR20R21- (V3), -CR22R23- CR24R25-W * - (V4), -CR26R27-W * - (V5), each of the radicals R6 or R27 in each case independently of one another are hydrogen, halogen, nitro, cyano, thiocyanate or a radical of the formula -B6 -D6, W * is in each case O, S, or a group of the formula N ( B7-D7), B1, B2, B3 and B7 independently of one another are a direct or divalent linking group of the formulas -C (= Z *) -, - C (= Z *) - Z ** -, - C (= Z *) - NH- or -C (= Z *) - NR * -, where Z * = O or S, Z ** = O or S, and R * = alkyl (C Cß), phenyl , phenyl- (C? -Ce) alkyl, (C3-C9) cycloalkyl or (C3-C9) cycloalkyl-alkyl (C? -C6), each of the last mentioned radicals are unsubstituted or substituted, by one or more radicals iFFtíl ^^^^^^ ^. ^ - ^^ mm ^^ ^ m * ti? ií i ^ íitat m¿a ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^. m, a ,,, t ^^ JMtÉÜJ HÉMi. selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, carboxyl, sulfo, cyano, thiocyanate, (C1-C4) alkoxy, haloalkoxy (C4), alkylthio (CC), haloalkylthio (C -? - C) , (C1-C4) monoalkylamino, dialkylamino (C1-C4), cycloalkyl (C3-Cg), [(C? -C4)] carbonyl, [(C4) alkoxy] carbonyl, aminocarbonyl, monoalkylaminocarbonyl (CrC4), dialkylaminocarbonyl (C C4), alkylsulfonyl (C -? - C4), haloalkylsulfonyl (C C4) and in the case of cyclic radicals besides (C1-C4) alkyl and haloalkyl (CC); B4, B5 and B6 independently of one another a direct bond or a divalent group of the formulas -O-, -S (O) p-, -S (O) pO-, -O -S (O) p-, - CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S, -O-CO-O-, -NR ° - , -O-NR0-, -NR ° -0-, -NR ° -CO-, -CO-NR0-, -O-CO-NR0- or -NR ° -CO-O-, where p is the integer 0 , 1 or 2 and R ° = hydrogen, (C1-C4) alkyl, phenyl, (C1-C4) alkyl, cycloalkyl (C3-Ce) or cycloalkyl (C3-Ce) -alkyl (CrC4), each of the latter 5 radicals mentioned are not substituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, cartyl, sulfo, cyano, thiocyanate, (C 1 -C 4) alkoxy, haloalkoxy (C 1 -C 4) ), (C 1 -C 4) alkylthio, haloalkylthio (C - β-C4), monoalkylamino (CC), dialkylamino (C 1 -C 4), cycloalkyl (C 3 -Cg), [alkyl (CrC)] carbonyl, [alkoxy (CrC 4) ] carbonyl, aminocarbonyl, monoalkylaminocarbonyl (C -? - C4), dialkylaminocarbonyl (CrC), alkylsulfonyl (CrC4), haloalkylsulfonyl (Ci-C4) and in the case of cyclic radicals furthermore alkyl (C -? - C) and haloalkyl (dC), D1, D2, D3, D4, D5 and D6 independently of one another are hydrogen, alkyl (Ci) -Cβ), phenyl, alkylphenyl (CrC4), cycloalkyl (C3-C6) or cycloalkyl (C3-C6) -alkyl (C? -C6), each of the last mentioned radicals are unsubstituted or substituted, preferably not substituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, carboxyl, sulfo, cyano, thiocyanate, (C -? - C4) alkoxy, alkylthio (CrC), haloalkylthio (C1-) C4), monoalkylamino (CrC4), dialkylamino (C -? - C), cycloalkyl (C3-Cg), [(C? -C) alkyl] carbonyl, [(C? -C4) alkoxy] carbonyl, aminocarbonyl, monoalkylaminocarbonyl ( CrC4), dialkylaminocarbonyl (Cr C), alkylsulfonyl (C1-C4), haloalkylsulfonyl (C1-C4) and in the case of cyclic radicals in addition alkyl (CrC4) and haloalkyl (CrC), (X) n is n substituents X, where the X independently from each other are halogen, hydroxyl, amino, nitrogen, formyl, carboxyl, cyano, thiocyanate, aminocarbonyl or alkyl (Ci-C4), alkoxy (C1-C4), alkylthio (CrC), monoalkylamino (C1-C4) , (C 1 -C 4) dialkylamino, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, [(C 1 -C 4) alkyl] carbonyl, [C 1 alkoxy] carbonyl, (C 1 -C 4) monoalkylaminocarbonyl, dialkylaminocarbonyl (Cr C ), N-alkanoylamino (Ci-Cß) or N-alkanoyl (CrC4) -N-alkylamino (CrC4), each of the last 13 radicals mentioned JOS are unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, cyano, thiocyanate, (C1-C4) alkoxy, haloalkoxy (C1-C4), alkylthio (C1-C4), monoalkylamino (C1-C4), dialkylamino (C1-C4) ), (C3-C6) cycloalkyl, (C3-C6) cycloalkylamino, [alkyl (CrC4)] carbonyl, [(C-? - C4) alkoxy] carbonyl, aminocarbonyl, monoalkylaminocarbonyl (C1-C4), dialkylaminocarbonyl ( C1-C4), phenyl, fe noxyl, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio and to -thiethyl heterocyclylamino, each of the last 8 mentioned radicals are unsubstituted or have one or more substituents selected from the group consisting of halogen, nitrogen, cyano, (C1-C4) alkyl, (C1-C4) alkoxy, alkylthio ( C1-C4), haloalkyl (CrC4), haloalkoxy (C -? - C), formyl, alkylcarbonyl (CrC) and alkoxycarbonyl (CrC), or cycloalkyl (C3-Cg), phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy , heterocyclicthio or heterocyclylamino, each of the last 9 mentioned radicals are unsubstituted or substituted, by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitrogen, formyl, carbonyl, cyano, thiocyanate, alkyl (C? -C4), haloalkyl (C1-C4), alkoxy (CrC4), haloalkoxy (C1-C4), alkylthio (C1-C4), haloalkylthio (C---C), monoalkylamino (C---C4), dialkylamino ( C -? - C4), cycloalkyl (C3-Ce), [(alkyl (CrC4)] carbonyl, [((C? -C4)] carbonyl, aminocarbonyl, monoalkylaminocarbon ilo (C1-C4) and dialkylaminocarbonyl (C1-C4), or two adjacent radicals X together are a fused ring having from 4 to 6 ring atoms and is carbocyclic or contains ring heteroatoms selected from the group consisting of O, S and N and which is not substituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4) alkyl and oxo, and n is 0, 1, 2 or 3.

5. A compound of the formula (I) or a salt thereof according to any of claims 1 to 4, wherein R2 is cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each of which is unsubstituted or substituted by one or more radicals selected from the group consisting of a group consisting of halogen, hydroxyl, cyano, thiocyanate, (C1-C4) alkyl, haloalkyl (dC), (C1-C4) alkoxy, haloalkoxy (CC), alkylthio (C1-C4), haloalkylthio (CC), alkylidene ( C1-C4), monoalkylamino (CrC4) and dialkylamino (C4), or heterocyclyl which is unsubstituted or substituted by rad selected from the group consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfonyl, cyano, thiocyanate, alkyl (C -? - C4), haloalkyl (C1-C4), alkoxy (C1-C4), haloalkoxy ( CrC4), (C1-C4) alkylthio, haloalkylthio (C1-C4), monoalkylamino (d-C4), dialkylamino (CrC4), cycloalkyl (C3-Ce), heterocyclyl having from 3 to 6 carbon atoms, [alkyl ( CrC4)] carbonyl, [alkoxy (CrC4)] carbonyl, aminocarbonyl, monoalkylaminocarbonyl (C1-C4), dialkylaminocarbonyl (dC), alkylsulfonyl (CrC4) and haloalkylsulfonyl (C1-C4).

6. A compound of the formula (I) or a salt thereof according to any of claims 1 to 5, wherein A1 is a radical of the formula -CH2-, -CH2CH2-, -CH2CH2CH2-, - CH2CH2CH2CH2 or -CH2CH2CH2CH2CH2- and A2 is a direct bond or a group of the formula -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, -CH2-O-CH2-, -CH2-O-CH2-CH2-, -CH2-S-CH2-, -CH2-S-CH2-CH2-, -CH2-CH2-S-CH2-, -CH2-NH-CH2-, -CH2-NH-CH2-CH2-, -CH2-CH2 -NH-CH2-, -CH2-N (CH3) -CH2-, -CH2-N (CH3) -CH2-CH2- or -CH2-CH2-N (CH3) -CH2-, and the number of the carbon of the total number of carbon atoms of the two radicals A1 and A2-R2 is a number from 6 to 20.

7. A process for the preparation of a compound of the formula (I) or a salt thereof. according to any of claims 1 to 6, which consists of a) reacting a compound of the formula (II) R1-Fu (II) in which Fu is a functional group selected from the group consisting of carboxylic ester, orthoester carboxylic acid, carboxylic acid chloride, carboxamide, carboxylic anhydride and trichloromethyl with a biguanidide of the formula (III) or an acid addition salt thereof or b) reacting a compound of the formula (IV) where Z1 is an exchangeable radical or leaving group with a suitable amine of the formula (V) or an acid addition salt thereof ..-..., .. ",. ? 'JK &- where, in the formulas (II), (lll), (IV) and (V), the radicals R1, R2, R3, R4, A1, A2 and X and n are as defined in formula (I).

8. A herbicidal or plant growth regulating composition, comprising one or more compounds of the formula (I) or salts thereof according to any of claims 1 to 6 and auxiliary ingredients of formulation conventionally used in the protection of crops.

9. A method for controlling harmful plants or for regulating the growth of plants, in which an effective amount of one or more compounds of the formula (I) or salts thereof is applied according to any of claims 1 to 6 to the plants, the seeds of the plants or the area under cultivation.

10. The use of a compound of formula (I) or a salt thereof according to any of claims 1 to 6 as herbicides or plant growth regulators.

11. The use as claimed in claim 10, wherein the compounds of the formula (I) or salts thereof are used to control harmful plants or to regulate growth in crops of useful or ornamental plants.

12. The use as claimed in claim 11, wherein the crop plants are transgenic crop plants.

13. A compound of the formula (III) or (V) according to claim 7 except the compound 1-cyclohexyl-2-phenylethylamine. j ^ d ^ aai