SUBSTITUTED 2,4-DIAMINO-1,3,5-TRIAZINES, PROCESSES FOR THEIR PREPARATION AND THEIR USE AS HERBICIDES AND PLANT GROWTH REGULATORS

Abstract

Substituted 2,4-diamino-1,3,5-triazines of the formula I and salts thereof, processes for their preparation and their use as herbicides and plant growth regulators are described. 1

Description

[0001] The invention relates to the technical area of herbicides and plant growth regulators, in particular to that of herbicides for the selective control of broad-leaved weeds and weed grasses in crops of useful plants.

[0002] From various publications, it is already known that certain 2,4-diamino-1,3,5-triazines have herbicidal properties. Thus, WO 97/00254 describes 2,4-diamino-1,3,5-triazines which carry a phenyl radical attached to an amino group via an ethylene, oxyethylene, aminoethylene, thioethylene or propylene chain. WO 97/08156 discloses 2,4-diamino-1,3,5-triazines in which a phenyl radical is attached to an amino group via an alkylene, alkenylenemethyl or alkynylenemethyl chain. WO 98115537 discloses 2,4-diamino-1,3,5-triazines which carry an aromatic or heterocyclic radical attached via a propylene or oxyethylene chain to an amino group. Finally, WO 98115539 mentions 2,4-diamino-1,3,5-triazines which carry a benzyl, naphthylmethyl, heterocyclyl or heterocyclyloxy radical attached via an ethylene chain to an amino group.

[0003] However, in practice the use of the 2,4-diamino-1,3,5-triazines known from these publications frequently entails disadvantages. Thus, the herbicidal or plant growth-regulatory activity of the known compounds is not always sufficient or, where the herbicidal activity is sufficient, undesirable damage to the crop plants is observed.

[0004] It is an object of the present invention to provide herbicidal and plant growth-regulatory compounds which overcome the disadvantages known from the prior art.

[0005] The object is achieved by 2,4-amino-1,3,5-triazines of the formula I, if appropriate also in the form of their salts, 2

[0006] in which

[0007] Aryl is an unsubstituted or substituted mono- or bicyclic aromatic radical having 5 to 14 ring atoms, 1, 2, 3 or 4 of which may in each case independently of one another originate from the group consisting of oxygen, sulfur and nitrogen;

[0008] —Y— is a divalent unit from the group consisting of —O—, —S—, —NR11—, —NR12CONR13—, —CO2—, —OCO2—, —OCONR14—, —SO—, —SO2—, —SO2O—, —OSO2O—, —SO2NR14—, —O—NR11—, —NR′—NR″—, in which R′ and R″ independently of one another are as defined for R14, and —(Y′—CRaRb—CRcRd); —Y″, in which Y′ and Y″ independently of one another are O, S, NH or N[(C1-C4)alkyl], Ra, Rb, Rc and Rd in each case independently of one another are H or (C1-C4)alkyl and i is an integer from 1 to 5, preferably 1, or a trivalent unit of the formula —O—N═,

[0009] m is 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2 or 3;

[0010] n is an integer from 1 to 10, preferably from 1 to 5, in particular 1, 2, 3 or 4, with the proviso that n is not 1 if m is zero and —Y— is —O—, —S—, —SO—, —SO2— or —NR11—,

[0011] R1, R2 in each case independently of one another are a radical from a group G1 which comprises hydrogen, (C1-C10)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C10)-alkoxy, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkoxy, aryl-(C1-C6)-alkyl and (C3-C8)-cycloalkyl-(C1-C6)-alkyl, where the cyclic moiety of the four last-mentioned radicals is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato and —B—X1, where —B— and X1 are as defined below, and where the non-cyclic moiety of the eight last-mentioned radicals from the group G1 is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato and —B—X2, where X2 is as defined below, and where the non-cyclic moiety of the radicals from the group G1 may in each case be interrupted by one or more identical or different heteroatoms from the group consisting of oxygen and sulfur, or

[0012] R1 and R2 of a (CR1R2) group form, together with the carbon atom which carries them, a carbonyl group, a group CR15R16 or a 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato and —B—X1, or

[0013] two R1 of two directly adjacent or not directly adjacent (CR1R2) groups together with the carbon atoms which carry or link them form an unsubstituted or substituted 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato and —B—X1, or

[0014] two R1 of two directly adjacent (CR1R2) groups together with the bond between the carbon atoms of the groups form a double bond, or two R1 and two R2 of two directly adjacent (CR1R2) groups together with the bond between the carbon atoms of the groups form a triple bond or else

[0015] R1 is a linkage point for the double bond in the case where Y is a trivalent unit ═N—O— adjacent to a CR1R2 group,

[0016] R3, R4 in each case independently of one another are a radical of a group G2 which comprises hydrogen, (C1-C10)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C10)-alkoxy, (C1-C10)-alkylthio, (C1-C10)-alkylsulfinyl, (C1-C10)-alkylsulfonyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkoxy, aryl, aryl-(C1-C6)-alkyl, aryl-(C1-C6)-alkoxy, (C3-C8)-cycloalkyl-(C1-C6)-alkyl, (C3-C8)-cycloalkyl-(C1-C6)-alkoxy, (C3-C8)-cycloalkoxy-(C1-C6)-alkyl and (C3-C8)-cycloalkoxy-(C1-C6)-alkoxy, where the cyclic moiety of the nine last-mentioned radicals is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato and —B—X1, where —B— and X1 are as defined below, and where the non-cyclic moiety of the sixteen last-mentioned radicals from the group G2 is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato and —B—X2, where X2 is as defined below, and where the non-cyclic moiety of the radicals from the group G2 may in each case be interruped by one or more identical or different heteroatoms from the group consisting of oxygen and sulfur, or

[0017] R3 and R4 together with the carbon atom which carries them form a carbonyl group, a group CR15R16 or a 3- to 6-membered ring, which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato and —B—X1, or

[0018] two R3 of two directly adjacent or not directly adjacent (CR3R4) groups together with the carbon atoms which carry or link them form an unsubstituted or substituted 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato and —B—X1; or else

[0019] two R3 of two directly adjacent (CR3R4) groups together with the bond between the carbon atoms of the groups form a double bond, or two R3 and two R4 of two directly adjacent (CR3R4) groups together with the bond between the carbon atoms of the groups form a triple bond, or else

[0020] R3 is a linkage point for the double bond in the case where Y is a trivalent unit —O—N═ adjacent to a CR3R4 group,

[0021] —B— is a direct bond or a divalent unit from the group consisting of —O—, —S—, —NR11—, —NR12CONR13—, —CO2—, —OCO2—, —OCONR14—, —SO—, —SO2—, —SO2O—, —OSO2O— and —SO2NR14—;

[0022] X1 is hydrogen, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C3-C8)-cycloalkyl or heterocyclyl having 3 to 9 ring atoms, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen and sulfur, and where the five last-mentioned radicals are unsubstituted or substituted by one or more identical or different halogen atoms;

[0023] X2 is hydrogen or heterocyclyl having 3 to 9 ring atoms, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen and sulfur, which is unsubstituted or substituted by one or more identical or different halogen atoms;

[0024] R5, R6 independently of one another are each a radical from the group G2, or

[0025] R3 and R5 of two directly adjacent or not directly adjacent (CR3R4) or (CR5R6) groups which with the carbon atoms which link them form an unsubstituted or substituted 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato and —B—X1, or

[0026] R5 and R6 together with the carbon atom which carries them form a carbonyl group, a group CR15R16 or a 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato and —B—X1, or

[0027] R6 is heterocyclyl,

[0028] R7 is hydrogen, amino, alkylcarbonyl, alkylamino or dialkylamino having in each case one to six carbon atoms in the alkyl radical, is an acyclic hydrocarbon or hydrocarbonoxy radical having in each case one to six carbon atoms, is a cyclic hydrocarbon or hydrocarbonoxy radical having in each case three to six carbon atoms or is heterocyclyl, heterocyclyloxy or heterocyclylamino having in each case three to six ring atoms and one to three hetero ring atoms from the group consisting of nitrogen, oxygen and sulfur, where each of the ten last-mentioned radicals is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, (C1-C4)-alkoxy, halogen-(C1-C4)-alkoxy, (C1-C4)-alkylthio, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-alkenyloxy, (C2-C4)-alkynyloxy, hydroxyl, amino, acylamino, alkylamino, dialkylamino, nitro, carboxyl, cyano, azido, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl, formyl, carbamoyl, mono- and di-(C1-C4)-alkylaminocarbonyl, (C1-C4)-alkylsulfinyl, halo-(C1-C4)-alkylsulfinyl, (C1-C4)-alkylsulfonyl, halo-(C1-C4)-alkylsulfonyl and, in the case of cyclic radicals, also (C1-C4)-alkyl and halo-(C1-C4)-alkyl,

[0029] R8 is (C1-C10)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, which are unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, cyano, nitro, thiocyanato, hydroxyl, (C1-C4)-alkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-alkylsulfonyl, phenyl, (C3-C9)-cycloalkyl, (C3-C9)-cycloalkoxy, and is heterocyclyl having three to six ring atoms and one to three hetero ring atoms from the group consisting of oxygen, nitrogen and sulfur, which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, amino, (C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy, is (C3-C8)-cycloalkyl, (C3-C8)-cycloalkoxy or a heterocyclyl radical having three to six ring atoms, where these three last-mentioned radicals are unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato, (C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy,

[0030] R9, R10 independently of one another are each hydrogen, amino, (C1-C10)-alkylcarbonyl, (C1-C10)-alkylamino, di-[(C1-C10)-alkyl]amino, (C1-C10)-alkyl, (C3-C8)-cycloalkyl, (C1-C10)-alkoxy, (C3-C8)-cycloalkoxy, heterocyclyl, heterocyclyloxy or heterocyclylamino having in each case 3 to 6 ring atoms and 1 to 3 hetero ring atoms from the group consisting of oxygen, nitrogen and sulfur, where each of the ten last-mentioned radicals is unsubstituted or substituted, or

[0031] R9 and R10 together with the nitrogen atom which carries them form a heterocycle having a total of three to six ring atoms and from among these one to four hetero ring atoms, where the other hetero ring atoms which may be present in addition to the nitrogen atom that is present are selected from the group consisting of oxygen, nitrogen and sulfur and where this heterocycle is unsubstituted or substituted,

[0032] R11 is hydrogen, amino, (C1-C10)-alkylamino, di-[(C1-C10)-alkyl]amino, (C1-C10)-alkyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkyl-(C1-C6)-alkyl, (C1-C10)-alkoxy, (C1-C6)-alkoxy-(C1-C6)-alkoxy, (C3-C8)-cycloalkoxy, (C1-C10)-alkylcarbonyl, where the nine last-mentioned radicals are unsubstituted or substituted,

[0033] R12, R13 independently of one another are each hydrogen, (C1-C10)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, phenyl, phenyl-(C1-C6)-alkyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkyl-(C1-C6)-alkyl, where the cyclic moiety of the four last-mentioned radicals is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of (C1-C4)-alkyl, halo-(C1-C4)-alkyl, (C1-C4)-alkoxy and halo-(C1-C4)-alkoxy, or

[0034] R12 and R13 together with the N—CO—N group which carries them form a 5- to 8-membered ring which, in addition to the two abovementioned nitrogen atoms, may contain a further heteroatom from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted,

[0035] R14 is hydrogen or in each case unsubstituted or substituted (C1-C10)-alkyl or (C3-C10)-cycloalkyl,

[0036] R15, R16 independently of one another are each hydrogen, aryl, (C1-C10)-alkoxy, aryl-(C1-C6)-alkyl, (C1-C10)-alkyl, (C1-C10)-alkylthio, where the five last-mentioned radicals are unsubstituted or substituted, and where the aliphatic carbon skeleton of the three last-mentioned radicals may be interrupted by one or more identical or different heteroatoms from the group consisting of oxygen and sulfur, or

[0037] R15 and R16 together with the carbon atom which carries them form a 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted.

[0038] The term aryl is to be understood as meaning, for example, phenyl, naphthyl, biphenyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl aziridinyl, azetidinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, thiazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, oxazinyl, thiazinyl, thiadiazinyl, oxadiazinyl, dithiazinyl, thioxazinyl, indolyl, benzoxazolyl, benzothiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, purinyl or naphthyridinyl. These aryl radicals may in principle, i.e. the structure of the ring system permitting, be attached to the remaining moiety of the molecule of the compound of the formula I at any position of the aryl radical.

[0039] If —Y— or —B— is an asymmetrical divalent unit, i.e. if there are two options for the attachment, in each case both options for the attachment of —Y— or —B— and the remainder of the molecule on the other hand are to be embraced by the formula I.

[0040] In the formula I and in all subsequent formulae, the carbon-containing radicals, such as alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio, and the corresponding radicals which are unsaturated and/or substituted in the carbon skeleton, such as alkenyl and alkynyl, can in each case be straight-chain or branched. Unless specifically mentioned otherwise, the lower carbon skeletons, for example those having 1 to 6 carbon atoms or in the case of unsaturated groups having 2 to 4 carbon atoms, are preferred for these radicals.

[0041] Alkyl radicals, including in composite meanings such as alkoxy, haloalkyl, etc., are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl- and alkynyl radicals have the meaning of the possible unsaturated radicals which correspond to the alkyl radicals; alkenyl, is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl; alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. The multiple bond may be in any position of the unsaturated radical.

[0042] Cycloalkyl is a carbocyclic saturated ring system having three to nine carbon atoms, for example cyclopropyl, cyclopentyl or cyclohexyl. In the case of composite radicals, such as (C3-C8)-cycloalkyl-(C1-C6)-alkyl, the first-mentioned radical may be in any position of the radical mentioned second.

[0043] In the case of a doubly substituted amino group, such as dialkylamino, these two substituents may be identical or different.

[0044] Halogen is fluorine, chlorine, bromine or iodine. Haloalkyl, -alkenyl and -alkynyl are alkyl, alkenyl or alkynyl which are partially or completely substituted by halogen, preferably by fluorine, chlorine and/or bromine, in particular by fluorine or chlorine, for example CF3, CHF2, CH2F, CF3CF2, CH2FCHCl, CCl3, CHCl2, CH2CH2Cl; haloalkoxy is, for example, OCF3, OCHF2, OCH2F, CF3CF2O, OCH2CF3 and OCH2CH2Cl; this applies correspondingly to haloalkenyl and other halogen-substituted radicals.

[0045] An acyl radical is the radical of an organic acid, for example the radical of a carboxylic acid and radicals of acids derived therefrom, such as the thiocarboxylic acid, unsubstituted or N-substituted iminocarboxylic acids or the radical of carbonic monoesters, unsubstituted or N-substituted carbaminic acid, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids. Acyl is, for example, formyl, alkylcarbonyl, such as (C1-C4)-alkylcarbonyl, phenylcarbonyl, where the phenyl ring is unsubstituted or substituted, for example as shown for phenyl above, or alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl or other radicals of organic acids.

[0046] A hydrocarbon radical is a straight-chain, branched or cyclic and saturated or unsaturated aliphatic or aromatic hydrocarbon radical, for example alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl and fluorenyl.

[0047] Substituted radicals, such as substituted hydrocarbon radicals, for example substituted alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, or substituted heterocyclyl are, for example, a radical which is derived from the unsubstituted parent compound and which is substituted by one or more identical or different other radicals, the substituents being, for example, one or more, preferably, unless mentioned otherwise, 1, 2 or 3 radicals, from the group consisting of halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, 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, and unsaturated aliphatic radicals which correspond to the abovementioned saturated hydrocarbon-containing radicals, such as alkenyl, alkynyl, alkenyloxy, alkynyloxy etc. Preferred radicals with carbon atoms are those having up to 4 carbon atoms. Preference is usually given to substituents from the group consisting of halogen, for example fluorine and chlorine, (C1-C4)-alkyl, preferably methyl or ethyl, (C1-C4)-haloalkyl, preferably trifluoromethyl, (C1-C4)-alkoxy, preferably methoxy or ethoxy, (C1-C4)-haloalkoxy, nitro and cyano. Particular preference is given here to the substituents methyl, methoxy and chlorine.

[0048] If the carbon chain of an alkyl, alkenyl or alkynyl radical is interrupted by more than one heteroatom, these heteroatoms are not to be directly adjacent.

[0049] Unless indicated otherwise, the term heterocycle means a saturated, unsaturated or heteroaromatic ring system which contains one or more heteroatoms, preferably from the group consisting of oxygen, sulfur and nitrogen. Examples include pyridine, pyrimidine, pyridazine, pyrazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, thiophene, thiazole, oxazole, oxetan, furan, pyrrole, pyrazole, imidazole, aziridine, oxiran, pyrrolidine, piperidine, piperazine, dioxolan, morpholine, tetrahydrofuran. The terms “heterocyclyl” and “heterocyclic radical” are also to be understood in this sense, i.e. as radicals which are derived from the above-mentioned heterocycles. If a heterocycle contains at least two heteroatoms, the condition applies that two oxygen atoms may not be directly adjacent. These heterocycles may in principle, i.e. the structure of the ring system permitting, be attached with the other moiety of the molecule of the compound of the formula I at any position of the heterocycle. Unless indicated otherwise, the heterocycle may be unsubstituted or substituted by one or more identical or different radicals. These radicals may be the radicals mentioned under “substituted hydrocarbon radicals”, and additionally also oxo. The oxo group may also be present at the hetero ring atoms which can exist in different oxidation states, for example at nitrogen and sulfur.

[0050] A ring may be saturated, partially saturated, completely unsaturated or aromatic.

[0051] The abovementioned examples of radicals or ranges of radicals which are included in the general terms, such as “alkyl”, “acyl”, “substituted radicals”, etc., are not meant to be a complete list. The general terms also include the definitions of radical ranges in groups of preferred compounds listed further below, in particular radical ranges which include the specific radicals from the examples in the tables.

[0052] Depending on the type and the attachment of the substituents, the compounds of the formula I may be present as stereoisomers. If, for example, one or more alkenyl groups are present, this may lead to diastereomers. If, for example, one or more asymmetric carbon atoms are present, this may lead to enantiomers and diastereomers. Stereoisomers can be obtained from the mixtures resulting in the preparation by using customary separation methods, for example chromatographic separation processes. Stereoisomers can also be prepared selectively by employing stereoselective reactions using optically active starting materials and/or auxiliaries. The invention also relates to all stereoisomers and mixtures thereof which are embraced by the formula I but not defined specifically.

[0053] The compounds of the formula I also include tautomers of the compounds which are formed by hydrogen shifts, such as, for example, enols and others, even if they do not formally correspond to the formula I.

[0054] Depending on the type of the substituents, the compounds of the formula I can form salts and are embraced by the term “compounds (of the formula) (I)”. In substituents with acidic properties, such as COOH and SO3H, the hydrogen atom of the acidic group may be replaced by an agriculturally suitable cation. These salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts or salts with organic amines. Salt formation may also occur by addition of an acid to basic substituents, such as, for example, amino and alkylamino. Acids which are suitable for this purpose are strong inorganic and organic acids, for example HCl, HBr, H2SO4 or HNO3. Such salts also form part of the subject matter of the invention.

[0055] The possibilities of combining the various substituents of the formula I are to be understood such that the general principles of construction of chemical compounds have to be observed, i.e. that no compounds are formed which are known to the person skilled in the art to be chemically unstable or impossible.

[0056] Preference is given to compounds of the formula I and salts thereof in which

[0057] aryl is an unsubstituted or substituted mono- or bicyclic aromatic radical having 5 to 10 ring atoms, 1, 2, 3 or 4 of which may in each case independently of one another originate from the group consisting of oxygen, sulfur and nitrogen, and/or

[0058] —Y— is a divalent unit from the group consisting of —O—, —S—, —NR11—, —NR12CONR13—, —CO2—, —OCONR14—, —SO—, —SO2—, —SO2O—, —SO2NR14—, —O—NR11—, —NH—NH— and —O—CRaRb—CRcRd—O—, in which Ra, Rb, Rc and Rd independently of one another are each H, CH3 or C2H5, or else a trivalent unit of the formula —O—N═ and/or

[0059] R1, R2 independently of one another are each a radical from a group G3 which comprises hydrogen, (C1-C8)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C6)-alkoxy, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkoxy, aryl-(C1-C6)-alkyl and (C3-C8)-cycloalkyl-(C1-C6)-alkyl, where the cyclic moiety of the four last-mentioned radicals is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, where —B— and X1 are as defined below, and where the non-cyclic moiety of the eight last-mentioned radicals from the group G3 is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X2, where X2 is as defined below, and where the non-cyclic moiety of the radicals from the group G3 may in each case be interrupted by one or more identical or different heteroatoms from the group consisting of oxygen and sulfur, or else

[0060] two R1 of two directly adjacent (CR1R2) groups together with the bond between the carbon atoms of the groups form a double bond, or two R1 and two R2 of two directly adjacent (CR1R2) groups together with the bond between the carbon atoms of the groups form a triple bond or

[0061] R1 is a linkage point for the double bond in the case where Y is a trivalent unit ═N—O— adjacent to a CR1R2 group, and/or

[0062] R3 and R4 independently of one another are each a radical from a group G4 which comprises hydrogen, (C1-C8)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C6)-alkoxy, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkoxy, aryl, aryl-(C1-C6)-alkyl, aryl-(C1-C6)-alkoxy, (C3-C8)-cycloalkyl-(C1-C6)-alkyl, (C3-C8)-cycloalkyl-(C1-C6)-alkoxy, (C3-C8)-cycloalkoxy-(C1-C6)-alkyl and (C3-C8)-cycloalkoxy-(C1-C6)-alkoxy, where the cyclic moiety of the nine last-mentioned radicals is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato and —B—X1, where —B— and X1 are as defined below, and where the non-cyclic moiety of the thirteen last-mentioned radicals from the group G4 in each case is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato and —B—X2, where X2 is as defined below, and where the non-cyclic moiety of the radicals from the group G4 may in each case be interrupted by one or two identical or different heteroatoms from the group consisting of oxygen and sulfur, or else two R1 of two directly adjacent (CR1R2) groups together with the bond between the carbon atoms of the groups form a double bond or else

[0063] two R3 of two directly adjacent (CR3R4) groups together with the bond between the carbon atoms of the groups form a double bond, or two R3 and two R4 of two directly adjacent (CR3R4) groups together with the bond between the carbon atoms of the groups form a triple bond or else

[0064] R3 is a linkage point for the double bond in the case where Y is a trivalent unit ═N—O— adjacent to a CR3R4 group, and/or

[0065] —B— is a direct bond or a divalent unit from the group consisting of —O—, —S—, —NR11—, —CO—, —CO2—, —OCO2—, —SO—, —SO2—, —SO2O— and —SO2NR14— and/or

[0066] X1 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl or heterocyclyl having 3 to 6 ring atoms, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen and sulfur, and where the five last-mentioned radicals are unsubstituted or substituted by one or more identical or different halogen atoms, and/or

[0067] X2 is hydrogen or heterocyclyl having 3 to 9 ring atoms, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen and sulfur, which is unsubstituted or substituted by 1, 2 or 3 identical or different halogen atoms, and/or

[0068] R5, R6 independently of one another are each a radical from the group G4 and/or

[0069] R7 is hydrogen, amino, alkylcarbonyl, alkylamino or dialkylamino having in each case one to four carbon atoms in the alkyl radical, is an acyclic or cyclic hydrocarbon radical having in each case one to six carbon atoms, or is heterocyclyl having three to six ring atoms and one to three hetero ring atoms from the group consisting of nitrogen, oxygen and sulfur, where each of the six last-mentioned radicals is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, (C1-C4)-alkoxy, halo-(C1-C4)-alkoxy, (C1-C4)-alkylthio, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-alkenyloxy, (C2-C4)-alkynyloxy, hydroxyl, amino, alkylamino, dialkylamino, nitro, carboxyl, cyano, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl, formyl, carbamoyl, mono- and di-(C1-C4)-alkylaminocarbonyl, (C1-C4)-alkylsulfonyl, halo-(C1-C4)-alkylsulfonyl and, in the case of cyclic radicals, also (C1-C4)-alkyl and halo-(C1-C4)-alkyl, and/or

[0070] R8 is (C1-C6)-alkyl, which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, cyano, nitro, thiocyanato, hydroxyl, (C1-C4)-alkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylsulfonyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, phenyl, (C3-C9)-cycloalkyl, (C3-C9)-cycloalkoxy and heterocyclyl having three to six ring atoms and one to three hetero ring atoms from the group consisting of oxygen, nitrogen and sulfur which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, amino, (C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy, is (C3-C8)-cycloalkyl or (C3-C8)-cycloalkoxy, where the two last-mentioned radicals are unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, (C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy, and/or

[0071] R9, R10 independently of one another are each hydrogen, amino, (C1-C6)-alkylcarbonyl, (C1-C6)-alkylamino, di-[(C1-C6)-alkyl]amino, (C1-C6)-alkyl, (C3-C8)-cycloalkyl, (C1-C6)-alkoxy, (C3-C8)-cycloalkoxy or heterocyclyl having 3 to 6 ring atoms and 1 to 3 hetero ring atoms from the group consisting of oxygen, nitrogen and sulfur, where each of the eight last-mentioned radicals is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, amino, hydroxyl and, in the case of cyclic radicals, also (C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy, and/or

[0072] R11 is hydrogen, amino, (C1-C6)-alkylamino, di-[(C1-C6)-alkyl]amino, (C1-C6)-alkyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkoxy, (C1-C6)-alkoxy-(C1-C6)-alkoxy, (C3-C8)-cycloalkoxy, (C1-C6)-alkylcarbonyl, where the nine last-mentioned radicals are unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, amino, hydroxyl and, in the case of cyclic radicals, also (C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy, and/or

[0073] R12, R13 independently of one another are each hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, phenyl, phenyl-(C1-C6)-alkyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkyl-(C1-C6)-alkyl, where the cyclic moiety of the four last-mentioned radicals is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of (C1-C4)-alkyl, halo-(C1-C4)-alkyl, (C1-C4)-alkoxy and halo-(C1-C4)-alkoxy, or

[0074] R12 and R13 together with the N—CO—N group which carries them form a 5- to 8-membered ring which, in addition to the two abovementioned nitrogen atoms, may contain a further heteroatom from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, (C1-C4)-alkyl and halo-(C1-C4)-alkyl;

[0075] R14 is hydrogen or (C1-C6)-alkyl or (C3-C8)-cycloalkyl, each of which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, phenyl, hydroxyl, (C1-C4)-alkoxy and halo-(C1-C4)-alkoxy and/or

[0076] R15 and R16 independently of one another are each hydrogen, phenyl, (C1-C6)-alkoxy, phenyl-(C1-C6)-alkyl, (C1-C6)-alkyl, (C1-C6)-alkylthio, where the five last-mentioned radicals are unsubstituted or substituted, and where the aliphatic carbon skeleton of the three last-mentioned radicals may be interrupted by one or more identical or different heteroatoms from the group consisting of oxygen and sulfur.

[0077] Preference is also given to compounds of the formula I and salts thereof in which

[0078] R1 and R2 of a (CR1R2) group together with the carbon atom which carries them form a carbonyl group, a group CR15R16 or 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, or

[0079] two R1 of two directly adjacent or not directly adjacent (CR1R2) groups together with the carbon atoms which carry or link them form an unsubstituted or substituted 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1.

[0080] Likewise, preference is given to compounds of the formula I in which

[0081] R3 and R4 together with the carbon atom which carries them form a carbonyl group, a group CR15R16 or a 3- to 6-membered ring, which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, or

[0082] two R3 of two directly adjacent or not directly adjacent (CR3R4) groups together with the carbon atoms which carry or link them form an unsubstituted or substituted 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1.

[0083] Moreover, preference is given to compounds of the formula I and salts thereof in which

[0084] R3 and R5 of two directly adjacent or not directly adjacent (CR3R4)— or (CR5R6)— groups together with the carbon atoms which link them form an unsubstituted or substituted 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, or

[0085] R5 and R6 together with the carbon atom which carries them form a carbonyl group, a group CR15R16 or a 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, or

[0086] R6 is heterocyclyl.

[0087] Likewise, preference is given to compounds of the formula I and salts thereof in which

[0088] R9 and R10 together with the nitrogen atom which carries them form a heterocycle having a total of three to six ring atoms and from among these one to four hetero ring atoms, where the other hetero ring atoms which may be present in addition to the nitrogen atom that is present are selected from the group consisting of oxygen, nitrogen and sulfur and where this heterocycle is unsubstituted or substituted by up to three identical or different radicals preferably from the group consisting of halogen, amino, hydroxyl, (C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy.

[0089] Moreover, preference is given to compounds of the formula I and salts thereof in which

[0090] R15 and R16 together with the carbon atom which carries them form a 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, (C1-C4)-alkyl and halo-(C1-C4)-alkyl.

[0091] Particular preference is given to compounds of the formula I and salts thereof in which

[0092] aryl is a mono- or bicyclic aromatic radical having 5 to 10 ring atoms, 1, 2, 3 or 4 of which may in each case independently of one another originate from the group consisting of oxygen, sulfur and nitrogen, which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, hydroxyl, amino, formyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl, halo-(C1-C4)-alkoxycarbonyl, halo-(C1-C4)-alkylcarbonyl, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkoxy, (C1-C4)-alkoxy-(C1-C4)-alkyl, halo-(C1-C4)-alkoxy-(C1-C4)-alkyl, halo-(C1-C4)-alkoxy-[halo-(C1-C4)-alkyl], (C1-C4)-alkoxy-[halo-(C1-C4)-alkyl], (C3-C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(C1-C4)-alkyl, (C3-C6)-cycloalkyl-[halo-(C1-C4)-alkyl], halo-(C3-C6)-cycloalkyl-[halo-(C1-C4)-alkyl], halo-(C3-C6)-cycloalkyl-(C1-C4)-alkyl, (C1-C6)-alkylamino, di-[(C1-C6)-alkyl]amino, (C1-C6)-alkylaminocarbonyl, aminosulfonyl, (C1-C6)-alkylaminosulfonyl, di-[(C1-C6)-alkyl]aminosulfonyl, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy,

[0093] —Y— is a divalent unit from the group consisting of —O—, —S—, —NR11—, —CO2—, —SO—, —SO2—, —SO2O— and —SO2NR14— or a unit from the group consisting of —NH—CO—NH— and —OCONH— or a unit from the group consisting of —O—NH—, —O—N═ and —OCH2CH2O—,

[0094] R1, R2 independently of one another are in each case a radical from a group G5 which comprises hydrogen, (C1-C6)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C6)-alkoxy, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkoxy, aryl-(C1-C6)-alkyl and (C3-C6)-cycloalkyl-(C1-C6)-alkyl, where the cyclic moiety of the four last-mentioned radicals is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, where —B— and X1 are as defined below, and where the non-cyclic moiety of the eight last-mentioned radicals from the group G5 is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X2, where X2 is as defined below, and where the non-cyclic moiety of the radicals from the group G5 may in each case be interrupted by one or more identical or different heteroatoms from the group consisting of oxygen and sulfur, or

[0095] two R1 of two directly adjacent (CR1R2) groups together with the bond between the carbon atoms of the groups form a double bond, or two R1 and two R2 of two directly adjacent (CR1R2) groups together with the bond between the carbon atoms of the groups form a triple bond or

[0096] R1 is a linkage point for the double bond in the case where Y is a trivalent unit ═N—O— adjacent to a CR1R2 group,

[0097] R3, R4 independently of one another are in each case a radical from a group G6 which comprises hydrogen, (C1-C6)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C6)-alkoxy, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkoxy, aryl, aryl-(C1-C4)-alkyl, aryl-(C1-C4)-alkoxy, (C3-C8)-cycloalkyl-(C1-C4)-alkyl, (C3-C8)-cycloalkyl-(C1-C4)-alkoxy, (C3-C8)-cycloalkoxy-(C1-C4)-alkyl and (C3-C8)-cycloalkoxy-(C1-C4)-alkoxy, where the cyclic moiety of the nine last-mentioned radicals is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, where —B— and X1 are as defined below, and where the non-cyclic moiety of the thirteen last-mentioned radicals from the group G6 is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X2, where X2 is as defined below, and where the non-cyclic moiety of the radicals from the group G6 may in each case be interrupted by a heteroatom from the group consisting of oxygen and sulfur, or else

[0098] two R3 of two directly adjacent (CR3R4) groups together with the bond between the carbon atoms of the groups form a double bond, or two R3 and two R4 of two directly adjacent (CR3R4) groups together with the bond between the carbon atoms of the groups form a triple bond or else

[0099] R3 is a linkage point for the double bond in the case where Y is a trivalent unit —O—N═ adjacent to a CR3R4 group, and

[0100] —B— is a direct bond or a divalent unit from the group consisting of —O—, —S—, —NR11—, —CO—, —CO2—, —SO—, —SO2— and —SO2NR14—,

[0101] X1 is hydrogen, (C1-C6)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C6)-cycloalkyl or heterocyclyl having 3 to 6 ring atoms, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen and sulfur, and where the five last-mentioned radicals are unsubstituted or substituted by up to five identical or different halogen atoms,

[0102] X2 is hydrogen or is heterocyclyl having 3 to 6 ring atoms, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen and sulfur, which is unsubstituted or substituted by 1, 2 or 3 identical or different halogen atoms,

[0103] R5, R6 independently of one another are each a radical from the group G6,

[0104] R7 is hydrogen, amino, alkylcarbonyl, alkylamino or dialkylamino having in each case one to four carbon atoms in the alkyl radical, or is an acyclic or cyclic hydrocarbon radical having in each case one to six carbon atoms, where each of the five last-mentioned radicals is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, (C1-C4)-alkoxy, halo-(C1-C4)-alkoxy, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-alkenyloxy, (C2-C4)-alkynyloxy, hydroxyl, amino, (C1-C4)-alkylamino, di-[(C1-C4)-alkyl]amino, nitro, carboxyl, cyano, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl, formyl, carbamoyl, (C1-C4)-alkylsulfonyl, halo-(C1-C4)-alkylsulfonyl and, in the case of cyclic radicals, also (C1-C4)-alkyl and halo-(C1-C4)-alkyl,

[0105] R8 is (C1-C6)-alkyl which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, cyano, hydroxyl, (C1-C4)-alkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylsulfonyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, phenyl, (C3-C9)-cycloalkyl, (C3-C9)-cycloalkoxy, is (C3-C8)-cycloalkyl or (C3-C8)-cycloalkoxy, where the two last-mentioned radicals are substituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, (C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy,

[0106] R9, R10 independently of one another are each hydrogen, amino, (C1-C4)-alkylcarbonyl, (C1-C4)-alkylamino, di-[(C1-C4)-alkyl]amino, (C1-C4)-alkyl, (C3-C8)-cycloalkyl, (C1-C4)-alkoxy, (C3-C8)-cycloalkoxy or heterocyclyl having 3 to 6 ring atoms and 1 to 3 hetero ring atoms from the group consisting of oxygen, nitrogen and sulfur, where each of the eight last-mentioned radicals is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen, amino, hydroxyl and, in the case of cyclic radicals, also (C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy,

[0107] R11 is hydrogen, amino, (C1-C4)-alkylamino, di-[(C1-C4)-alkyl]amino, (C1-C4)-alkyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkyl-(C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C3-C8)-cycloalkoxy, (C1-C4)-alkylcarbonyl, where the nine last-mentioned radicals are unsubstituted or substituted by one or more identical or different halogen atoms and, in the case of cyclic radicals, also (C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy,

[0108] R14 is hydrogen or (C1-C4)-alkyl or (C3-C6)-cycloalkyl, each of which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, (C1-C4)-alkoxy and halo-(C1-C4)-alkoxy and/or

[0109] R15, R16 independently of one another are each hydrogen, phenyl, (C1-C4)-alkoxy, phenyl-(C1-C4)-alkyl, (C1-C4)-alkyl, (C1-C4)-alkylthio, where the five last-mentioned radicals are unsubstituted or substituted by one or more identical or different halogen atoms and, in the case of cyclic radicals, also by one or more identical or different radicals from the group consisting of halogen, (C1-C4)-alkyl and halo-(C1-C4)-alkyl.

[0110] Preference is also given to compounds according to the invention of the formula I which only contain one or more of the abovementioned preferred radicals.

[0111] Particular preference is also given to compounds of the formula I, in which

[0112] R1 and R2 of a (CR1R2) group together with the carbon atom which carries them form a carbonyl group, a group CR15R16 or a 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, or

[0113] two R1 of two directly adjacent or not directly adjacent (CR1R2) groups together with the carbon atoms which carry or link them form an unsubstituted or substituted 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1.

[0114] Particular preference is likewise given to compounds of the formula I in which

[0115] R3 and R4 together with the carbon atom which carries them form a carbonyl group, a group CR15R16 or a 3- to 6-membered ring, which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, or

[0116] two R3 of two directly adjacent or not directly adjacent (CR3R4) groups together with the carbon atoms which carry or link them form an unsubstituted or substituted 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1.

[0117] Moreover, particular preference is given to compounds of the formula I in which

[0118] R3 and R5 of two directly adjacent or not directly adjacent (CR3R4)— or (CR5R6)— groups together with the carbon atoms which link them form an unsubstituted or substituted 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, or

[0119] R5 and R6 together with the carbon atom which carries them form a carbonyl group, a group CR15R16 or a 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato and —B—X1, or

[0120] R6 is heterocycyl.

[0121] Particular preference is also given to compounds of the formula I in which

[0122] R9 and R10 together with the nitrogen atom which carries them form a heterocycle having a total of three to six ring atoms and from among these one to four hetero ring atoms, where the other hetero ring atoms which may be present in addition to the nitrogen atom that is present are selected from the group consisting of oxygen, nitrogen and sulfur and where this heterocycle is unsubstituted or substituted.

[0123] Particular preference is likewise given to compounds of the formula I in which

[0124] R15 and R16 together with the carbon atom which carries them form a 3-6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen, (C1-C4)-alkyl and halo-(C1-C4)-alkyl.

[0125] Very particular preference is given to compounds of the formula I in which

[0126] aryl is phenyl, naphthyl, pyridinyl, pyrimidinyl, furanyl, benzofuranyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, oxadiazolyl or thienyl, each of which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, hydroxyl, amino, formyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkoxy, (C1-C4)-alkylamino, di-[(C1-C4)-alkyl]amino, aminocarbonyl, (C1-C4)-alkylaminocarbonyl, di-(C1-C4)-alkylaminocarbonyl, aminosulfonyl, (C1-C4)-alkylaminosulfonyl, di-[(C1-C4)-alkyl]aminosulfonyl, halo-(C1-C4)-alkyl, halo-(C1-C4)-alkoxy, (C1-C2)-alkylthio, (C1-C2)-alkylsulfinyl, (C1-C2)-alkylsulfonyl, halo-(C1-C2)-alkylthio, halo-(C1-C2)-alkylsulfinyl and halo-(C1-C2)-alkylsulfonyl;

[0127] —Y— is a divalent unit from the group consisting of —O—, —S—, —NR11—, —CO2—, —SO— and —SO2— or else a divalent unit from the group consisting of —NH—CO—NH— and —O—CO—NH-or else a unit from the group consisting of —O—NH—, —O—N═ and —OCH2CH2O—,

[0128] m is an integer from 0 to 5, preferably 0, 1, 2 or 3, in particular O or 1;

[0129] n is an integer from 1 to 5, preferably 1, 2, 3 or 4, in particular 1, 2 or 3;

[0130] R1, R2 independently of one another are each a radical from a group G7 which comprises (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkoxy, hydrogen, (C3-C6)-Cycloalkyl, where the last-mentioned radical is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen and —B—X1, and where the four first-mentioned radicals from the group G7 are unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen and —B—X2, where X2 is as defined below, or else

[0131] R1 and R2 together with the carbon atom which carries them form a carbonyl group, or else

[0132] R1 is a linkage point for the double bond in the case where Y is a trivalent unit ═N—O— which is adjacent to a CR1R2 group, and

[0133] R3, R4 independently of one another are each a radical from a group G8 which comprises hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C6)-alkoxy, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkoxy, aryl, aryl-(C1-C2)-alkyl, aryl-(C1-C2)-alkoxy, (C3-C6)-cycloalkyl-(C1-C2)-alkyl and (C3-C8)-cycloalkoxy-(C1-C4)-alkyl, where the cyclic moiety of the seven last-mentioned radicals is in each case unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, where —B— and X1 are as defined below, and where the non-cyclic moiety of the eleven last-mentioned radicals from the group G8 is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X2, where X2 is as defined below, or else

[0134] R3 and R4 together with the carbon atom which carries them form a carbonyl group, or else

[0135] R3 is a linkage point for the double bond in the case where Y is a trivalent unit —O—N═ which is adjacent to a CR3R4 group,

[0136] —B— is a direct bond or a divalent unit from the group consisting of —O—, —S—, —NR11—, —CO— and —CO2—;

[0137] X1 is hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or (C3-C6)-cycloalkyl, the four last-mentioned radicals of which are unsubstituted or substituted by up to five identical or different halogen atoms,

[0138] X2 is hydrogen or heterocyclyl having 3 to 6 ring atoms, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen or sulfur, which is unsubstituted or substituted by one or more identical or different halogen atoms,

[0139] R5 is hydrogen, (C1-C4)-alkyl, halo-(C1-C4)-alkyl or (C3-C6)-cycloalkyl,

[0140] R6 is hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkoxy, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C4)-alkyl, (C3-C6)-cycloalkoxy-(C1-C4)-alkyl, (C3-C6)-cycloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkyl or halo-(C1-C4)-alkyl,

[0141] R7 is hydrogen, amino or (C1-C4)-alkyl,

[0142] R8 (C1-C4)-alkyl, halo-(C1-C4)-alkyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl-(C1-C4)-alkyl,

[0143] R9, R10 independently of one another are each hydrogen, amino, formyl or (C1-C4)-alkyl, or

[0144] R11 is hydrogen, amino, (C1-C4)-alkylamino, di-[(C1-C4)-alkyl]amino, (C1-C4)-alkyl or (C3-C6)-cycloalkyl, where the five last-mentioned radicals are unsubstituted or substituted by one or more identical or different halogen atoms, and/or

[0145] R14 is hydrogen or (C1-C4)-alkyl.

[0146] Particular preference is also given to compounds according to the invention of the formula I which contain only one or more of the abovementioned preferred radicals.

[0147] Very particular preference is also to given to compounds of the formula I in which two directly adjacent or not directly adjacent (CR1R2) groups together with the carbon atoms which carry or link them form a 3-, 5- or 6-membered ring which may contain up to 2 heteroatoms from the group consisting of oxygen, sulfur and nitrogen and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen and —B—X1.

[0148] Very particular preference is likewise given to compounds of the formula I in which two R3 of two directly adjacent or not directly adjacent (CR3R4) groups together with the carbon atoms which carry or link them form a 3-, 5- or 6-membered ring which may contain up to two heteroatoms from the group consisting of oxygen, sulfur and nitrogen and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen and —B—X1.

[0149] Very particular preference is likewise given to compounds of the formula I in which

[0150] R3 and R5 of two directly adjacent or not directly adjacent (CR3R4)— or (CR5R6) groups together with the carbon atoms which link them form a 3-, 5- or 6-membered ring which may contain up to two heteroatoms from the group consisting of oxygen, sulfur and nitrogen and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen and —B—X1.

[0151] Moreover, very particular preference is given to compounds of the formula I in which

[0152] R9 and R10 together with the carbon atom which carries them form a heterocycle having three to six ring atoms and one to two hetero ring atoms, where the other hetero ring atoms which may be present in addition to the nitrogen atom which is present are selected from the group consisting of oxygen and nitrogen.

[0153] The present invention also provides processes for preparing the compounds of the formula I or salts thereof, which comprise

[0154] a) reacting a compound of the formula (II)

R8-Fu  (II)

[0155] in which Fu is a functional group from the group consisting of carboxylic ester, carboxylic orthoester, carbonyl chloride, carboxamide, carboxylic anhydride and trichloromethyl

[0156] with a biguanidide of the formula (III) or an acid addition salt thereof 3

[0157] or

[0158] b) reacting a compounds of the formula (IV) 4

[0159] in which Z1 is an exchangeable radical or a leaving group, for example chlorine, trichloromethyl, (C1-C4)-alkylsulfonyl or unsubstituted or substituted phenyl-(C1-C4)-alkylsulfonyl or (C1-C4)-alkylphenylsulfonyl, with a suitable amine of the formula (V) or an acid addition salt thereof 5

[0160] where in the formulae (II), (III), (IV) and (V) the radicals R1 to R10, Y and n and m are as defined under formula (I).

[0161] The compounds of the formulae (II) and (III) are preferably reacted base-catalyzed 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 between 20° C. and 60° C. If acid addition salts of the formula (III) are used, these are usually liberated in situ with the aid of a base. Suitable bases or basic catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alkoxides, alkaline earth metal hydroxides, alkaline earth 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 employed, for example, in the range of from 0.1 to 3 molar equivalents, based on the compound of the formula (III). The compound of the formula (II) can be employed, in relation to the compound of the formula (III) for example, in equimolar amounts or in an excess of up to 2 molar equivalents. In principle, the corresponding processes are known from the literature (compare: Comprehensive Heterocyclic Chemistry, A. R. Katritzky, C. W. Rees, Pergamon Press, Oxford, N.Y., 1984, Vol.3; Part 2B; ISBN 0-08-030703-5, p.290).

[0162] The compounds of the formulae (IV) and (V) are preferably reacted base-catalyzed in an inert organic solvent, such as, for examle, THF, dioxane, acetonitrile, DMF, methanol and ethanol, at temperatures between −10° C. and the boiling point of the solvent or solvent mixture in question, preferably at from 20° C. to 60° C.; the compound (V), if it is employed as an acid addition salt, is liberated in situ with a base, if appropriate. Suitable bases or basic catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alkoxides, alkaline earth metal hydroxides, alkaline earth 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 usually employed in the range from 1 to 3 molar equivalents, based on the compound of the formula (IV), and the compound of the formula (IV) can be employed, for example, in equimolar amounts based on the compound of the formula (V), or in an excess of up to 2 molar equivalents. In principle, the corresponding processes are known from the literature (cf. Comprehensive Heterocyclic Chemistry, A. R. Katritzky, C. W. Rees, Pergamon Press, Oxford, N.Y., 1984, Vol.3, Part 2B, p. 482).

[0163] The starting materials of the formulae (II), (III), (IV) and (V) are either commercially available, or they can be prepared by or analogously to processes known from the literature. The compounds can also be prepared, for example, by one of the processes described below.

[0164] The compound of the formula (IV), or a direct presursor thereof, can be prepared, for example, as follows:

[0165] 1. Reaction of a compound of the formula (II) with an amidinothiourea derivative of the formula (VI), 6

[0166] in which Z2 is (C1-C4)-alkyl or phenyl-(C1-C4)-alkyl and R9 and R10 are as defined under formula (I) gives compounds of the formula (IV) in which Z1=—SZ2.

[0167] 2. Reaction of a n amidine of the formula (VII) or an acid addition salt thereof, 7

[0168] in which R8 is as defined under formula (I)

[0169] with an N-cyano dithioiminocarbonate of the formula (VIII), 8

[0170] in which Z3 is (C1-C4)-alkyl or phenyl-(C1-C4)-alkyl gives compounds of the formula (IV) in which Z1=—S-Z3.

[0171] 3. Reaction of an alkali metal dicyanamide with a carboxylic acid derivative of the abovementioned formula (II) gives compounds of the formula (IV) in which Z1=NH2.

[0172] 4. Reaction of trichloroacetonitrile with a nitrile of the formula (IX),

R8—CN  (IX)

[0173] in which R8 is as defined under formula (I) initially gives compounds of the formula (X), 9

[0174] in which Z1 and Z4 are each CCl3 which, by subsequent reaction with compounds of the formula HNR9R10 (R9 and R10 as under formula (I)) give compounds of the formula (IV), in which Z1=CCl3.

[0175] The reaction of the carboxylic acid derivatives of the formula (II) with the amidinothiourea derivatives of the formula (VI) is preferably carried out base-catalyzed in an organic solvent, such as, for example, acetone, THF, dioxane, acetonitrile, DMF, methanol, ethanol, at temperatures from −10° C. to the boiling point of the solvent, preferably at from 0° C. to 20° C. However, the reaction can also be carried out in water or in aqueous solvent mixtures comprising one or more of the abovementioned organic solvents. If (VI) is employed as acid addition salt, it can be liberated in situ using a base, if appropriate. Suitable bases or basic catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alkoxides, alkaline earth metal hydroxides, alkaline earth 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 employed, for example, in the range of from 1 to 3 molar equivalents, based on the compound of the formula (VI). Compounds of the formulae (II) and (VI) can be employed, for example, in equimolar amounts, or with an excess of up to 2 molar equivalents of the compound of the formula (II). In principle, the corresponding processes are known from the literature (cf.: H. Eilingsfeld, H. Scheuermann, Chem. Ber.; 1967, 100, 1874), the corresponding intermediates of the formula (IV) are novel.

[0176] The reaction of the amidines of the formula (VII) with the N-cyano dithioiminocarbonates of the formula (VIII) is preferably carried out base-catalyzed in an inert organic solvent, such as, for example, acetonitrile, DMF, dimethylacetamide (DMA), N-methylpyrrolidone (NMP), methanol and ethanol, at temperatures from −10° C. to the boiling point of the solvent, preferably at from 20° C. to 80° C. If (VII) is employed as acid addition salt, it can be liberated in situ using a base, if appropriate. Suitable bases or basic catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alkoxides, alkaline earth metal hydroxides, alkaline earth 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 employed, for example, in the range of from 1 to 3 molar equivalents, based on the compound of the formula (VIII), compounds of the formulae (VII) and (VIII) can usually be employed in equimolar amounts or in an excess of 2 molar equivalents of the compound of the formula (II). In principle, the corresponding processes are known from the literature (cf.: T. A. Riley, W. J. Henney, N. K. Dailey, B. E. Wilson, R. K Robins; J. Heterocyclic Chem.; 1986, 23 (6), 1706-1714), the corresponding intermediates of the formula (IV) are novel.

[0177] Intermediates of the formula (X) where Z1=chlorine can be prepared by reacting alkali metal dicyanamide with a carboxylic acid derivative of the formula (II), in which case Fu is preferably the functional group carbonyl chloride or carboxamide. The reaction components are, for example, reacted 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 from 20° C. to 80° C., and the resulting intermediates can be chlorinated in situ using an appropriate chlorinating reagent, for example phosphorus oxychloride. Suitable acids are, for example, hydrohalic acids, such as HCl, or else Lewis acids, such as, for example, AlCl3 or BF3 (cf. U.S. Pat. No. 5,095,113).

[0178] Intermediates of the formula (X) where Z1, Z4=trihalomethyl can be prepared by reacting the corresponding trihaloacetonitriles with a carbonitrile of the formula (IX). The reaction components are, for example, reacted with acid catalysis in an inert organic solvent such as toluene, chlorobenzene or chlorinated hydrocarbons at temperatures between −40□C and the boiling point of the solvent, preferably at from −10□C to 30□C. Examples of suitable acids are hydrohalic acids such as HCl or else Lewis acids such as AlCl3 or BF3 (cf. EP-A-1 30 939).

[0179] Intermediates of the formula (IV) in which Z1=(C1-C4)alkylmercapto or unsubstituted phenyl-(C1-C4)-alkylmercapto can be converted in an inert organic solvent, for example toluene, chlorobenzene, chlorinated hydrocarbons or others, at temperatures between −40□C and the boiling point of the solvent, preferably at from 20□C to 80□C, using an appropriate chlorinating reagent, for example elemental chlorine or phosphorus oxychloride, to more reactive chlorotriazines of the formula (IV), in which Z1 is Cl (cf. J. K Chakrabarti, D. E. Tupper; Tetrahedron 1975, 31(16), 1879-1882).

[0180] Intermediates of the formula (IV) in which Z1=(C1-C4)alkylmercapto or unsubstituted or substituted phenyl-(C1-C4)-alkylmercapto or (C1-C4)alkyl-phenylthio can be oxidized in an appropriate solvent, 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 from 20□C to 80□C, using a suitable oxidation reagent such as m-chloroperbenzoic acid, hydrogen peroxide, potassium peroxomonosulfate (cf.: T. A. Riley, W. J. Henney, N. K. Dalley, B. E. Wilson, R. K. Robins; J. Heterocyclic Chem.; 1986, 23 (6), 1706-1714).

[0181] For the preparation of the acid addition salts of the compounds of the formula (I), suitable acids are the following: hydrohalic acids such as hydrochloric acid or hydrobromic acid, and also phosphoric acid, nitric acid, sulfuric acid, mono- or bifunctional carboxylic acids 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 the customary methods of forming salts, for example by dissolving a compound of the formula (I) in an appropriate organic solvent such as, for example, methanol, acetone, methylene chloride or benzine and adding the acid at temperatures from 0 to 100□C, and can be isolated in a known manner, for example by filtration, and can if desired be purified by washing with an inert organic solvent.

[0182] The base addition salts of the compounds of formula (I) are preferably prepared in inert polar solvents such as, for example, water, methanol or acetone at temperatures from 0 to 100° C. Examples of suitable bases for preparing the salts according to the invention are alkali metal carbonates, such as potassium carbonate, alkali metal hydroxides and alkaline earth metal hydroxides, for example 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 and potassium tert-butoxide, or ammonia or ethanolamine.

[0183] By the “inert solvents” mentioned in the above process variants, solvents are meant which are in each case inert under the respective reaction conditions but which need not be inert under any reaction conditions.

[0184] The novel compounds of the formulae have an outstanding herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous weeds. The active compounds also act effectively against difficult-to-control perennial weeds which produce shoots from rhizomes, rootstocks or other perennial organs. In this context it does not matter whether the substances are applied before sowing, pre-emergence or post-emergence. Individually, examples may be mentioned of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention, without such mention being intended to restrict the invention to specific species. Examples of monocotyledonous weed species against which the active compounds act effectively are Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and Cyperus species from the annual group and examples of perennial species are Agropyron, Cynodon, Imperata and Sorghum and also perennial Cyperus species. In the case of dicotyledonous weed species, the spectrum of action extends to species such as, for example, Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, lpomoea, Matricaria, Abutilon and Sida among the annuals and Convolvulus, Cirsium, Rumex and Artemisia among the perennial weeds. The novel active compounds also display outstanding control of weeds which occur under the specific growing conditions in rice, examples being Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus.

[0185] Where the novel compounds are applied to the surface of the soil before germination, either the weed seedlings are prevented completely from emerging, or the weeds grow until they reach the cotyledon stage, but then stop growing and, finally, die off completely after three to four weeks have elapsed. Where the active compounds are applied post-emergence to the green parts of plants, there is likewise a very rapid and drastic termination of growth after treatment, and the weed plants remain at the growth stage they were at at the time of application, or die off completely after a certain time, so that in this manner competition from weeds, which is damaging to the crop plants, is eliminated very early on and in a sustained manner.

[0186] Even though the novel compounds have an excellent herbicidal activity with respect to monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example wheat, barley, rye, rice, maize, sugar beet, cotton and soya, suffer only minimal or zero damage. For these reasons the present compounds are highly suitable for the selective control of unwanted plant growth in crops of agriculturally useful plants or in plantations of ornamentals.

[0187] Owing to their herbicidal and plant growth-regulatory properties, the active compounds can also be employed for controlling harmful plants in crops of genetically engineered plants which are known or still to be developed. The transgenic plants generally have particularly advantageous properties, for example resistance to certain pesticides, in particular certain herbicides, resistance to plant diseases or causative organisms of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other particular properties relate, for example, to the quantity, quality, storage-stability, composition and to specific ingredients of the harvested product. Thus, transgenic plants having an increased starch content or a modified quality of the starch or those having a different fatty acid composition of the harvested product are known.

[0188] The use of the compounds according to the invention of the formula I or their salts in economically important transgenic crops of useful and ornamental plants, for example of cereal, such as wheat, barley, rye, oats, millet, rice, maniok and corn, or else in crops of sugarbeet, cotton, soya, rapeseed, potato, tomato, pea and other vegetable species is preferred. The compounds of the formula I can preferably be used as herbicides in crops of useful plants which are resistant or which have been made resistant by genetic engineering toward the phytotoxic effects of the herbicides.

[0189] Conventional ways for preparing novel plants which have modified properties compared to known plants comprise, for example, traditional cultivation methods and the generation of mutants. Alternatively, novel plants having modified properties can be generated with the aid of genetic engineering methods (see, for example, EP-A 0 221 044, EP-A 0 131 624). For example, there have been described several cases of

[0190] genetically engineered changes in crop plants in order to modify the starch synthesized in the plants (for example WO 92/11376, WO 92/14827, WO 91/19806),

[0191] transgenic crop plants which are resistant to certain herbicides of the glufosinate type (cf., for example, EP-A 0 242 236, EP-A 0 242 246) or glyphosate type (WO 92/00377), or of the sulfonylurea type (EP-A 0 257 993, U.S. Pat. No. 5,013,659),

[0192] transgenic crop plants, for example cotton, having the ability to produce Bacillus thuringiensis toxins (Bt toxins) which give the plants resistance to certain pests (EP-A 0 142 924, EP-A 0 193 259),

[0193] transgenic crop plants having a modified fatty add composition (WO 91113972).

[0194] Numerous molecular biological techniques which allow the preparation of novel transgenic plants having modified properties are known in principle; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Gene und Klone” [Genes and Clones], VCH Weinheim, 2nd edition 1996, or Christou, “Trends in Plant Science” 1 (1996) 423-431.

[0195] In order to carry out such genetic engineering manipulations, it is possible to introduce nucleic acid molecules into plasmids which allow a mutagenesis or a change in the sequence to occur by recombination of DNA sequences. Using the abovementioned standard processes it is possible, for example, to exchange bases, to remove partial sequences or to add natural or synthetic sequences. To link the DNA fragments with each other, it is possible to attach adaptors or linkers to the fragments.

[0196] Plant cells having a reduced activity of a gene product can be prepared, for example, by expressing at least one appropriate antisense-RNA, a sense-RNA to achieve a cosuppression effect, or by expressing at least one appropriately constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product.

[0197] To this end it is possible to employ both DNA molecules which comprise the entire coding sequence of a gene product including any flanking sequences that may be present, and DNA molecules which comprise only parts of the coding sequence, it being necessary for these parts to be long enough to cause an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product but which are not entirely identical.

[0198] When expressing nucleic acid molecules in plants, the synthesized protein can be localized in any desired compartment of the plant cells. However, to achieve localization in a certain compartment, it is, for example, possible to link the coding region with DNA sequences which ensure localization in a certain 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. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).

[0199] The transgenic plant cells can be regenerated to whole plants using known techniques. The transgenic plants can in principle be plants of any desired plant species, i.e. both monocotyledonous and dicotyledonous plants.

[0200] In this manner, it is possible to obtain transgenic plants which have modified properties by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or by expression of heterologous (=foreign) genes or gene sequences.

[0201] The compounds according to the invention can preferably be used in transgenic crops which are resistant to herbicides from the group consisting of the sulfonylureas, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active compounds.

[0202] When using the active compounds according to the invention in transgenic crops, in addition to the effects against harmful plants which can be observed in other crops, there are frequently effects which are specific for the application in the respective transgenic crop, for example a modified or specifically broadened spectrum of weeds which can be controlled, modified application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crops are resistant, and an effect on the growth and the yield of the transgenic crop plants.

[0203] The invention therefore also provides for the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.

[0204] Furthermore, the substances according to the invention exhibit outstanding growth-regulatory properties in crop plants. They intervene with a regulatory action in the endogenous plant metabolism and can therefore be employed for the targeted control of plant contents and for facilitating the harvest, for example by provoking desiccation and stunted growth. Moreover, they are also suitable for generally controlling and inhibiting unwanted vegetative growth without killing the plants in doing so. In the case of numerous monocotyledonous and dicotyledonous crops, inhibition of vegetative growth plays an important role, since it allows lodging to be reduced or prevented completely.

[0205] The invention also provides herbicidal and plant growth-regulatory compositions comprising compounds of the formula I. The novel compounds can be applied in the form of customary formulations, known to the person skilled in the art, such as wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules.

[0206] The compounds of the formula I can be formulated in various ways depending on the prevailing biological and/or chemico-physical parameters. Examples of suitable formulation options are: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), seed-dressing compositions, granules for broadcasting and soil application, granules (GR) in the form of microgranules, spray granules, coating granules and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes. These individual formulation types are known in principle and are described, for example, in Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th. Edition, 1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y., 1973; K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

[0207] The necessary formulation auxiliaries, such as inert materials, surfactants, solvents and other additives, are likewise known and are described, for example, in Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y. 1963; 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, “Grenzflächenaktive Äthylenoxidaddukte” [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986.

[0208] Wettable powders are preparations which are uniformly dispersible in water and which contain, in addition to the active compound and as well as a diluent or inert substance, surfactants of the ionic and/or nonionic type (wetting agents, dispersants), for example polyethoxylated alkyl phenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol polyglycol ethersulfates, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurinate. To prepare the wettable powders, the herbicidally active compounds are finely ground, for example in customary apparatus such as hammer mills, fan mills and air-jet mills, and are mixed simultaneously or subsequently with the formulation auxiliaries.

[0209] Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else relatively high-boiling aromatic compounds or hydrocarbons or mixtures of the organic solvents, with the addition of one or more surfactants of the ionic and/or nonionic type (emulsifiers). Examples of emulsifiers which can be used are calcium alkylarylsulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.

[0210] Dusts are obtained by grinding the active compound with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0211] Suspension concentrates can be water- or oil-based. They can be prepared, for example, by wet milling using commercially customary bead mills, with or without the addition of surfactants as already mentioned above, for example, in the case of the other formulation types.

[0212] Emulsions, for example oil-in-water emulsions (EW), can be prepared for example by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and, if desired, surfactants as already mentioned above, for example, in the case of the other formulation types.

[0213] Granules can be prepared either by spraying the active compound onto adsorptive, granulated inert material or by applying active-compound concentrates to the surface of carriers such as sand, kaolinites or granulated inert material, by means of adhesive binders, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active compounds can also be granulated in the manner which is customary for the preparation of fertilizer granules, if desired as a mixture with fertilizers.

[0214] Water-dispersible granules are generally prepared by the customary processes, such as spray-drying, fluidized-bed granulation, disk granulation, mixing using high-speed mixers, and extrusion without solid inert material.

[0215] For the preparation of disk fluidized-bed, extruder and spray granules, see for example processes in “Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; J. E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff.; “Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.

[0216] For further 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 Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0217] The agrochemical formulations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of active compound of the formula I. In wettable powders the concentration of active compound is, for example, from about 10 to 90% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In emulsifiable concentrates the concentration of active compound can be from about 1 to 90%, preferably from 5 to 80%, by weight. Formulations in the form of dusts contain from 1 to 30% by weight of active compound, preferably most commonly from 5 to 20% by weight of active compound, while sprayable solutions contain from about 0.05 to 80%, preferably from 2 to 50%, by weight of active compound. In the case of water-dispersible granules the content of active compound depends partly on whether the active compound is in liquid or solid form and on the granulation auxiliaries, fillers, etc. that are used. In water-dispersible granules the content of active compound is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

[0218] In addition, said formulations of active compound may comprise the tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors and pH and viscosity regulators which are customary in each case.

[0219] Based on these formulations it is also possible to produce combinations with other pesticidally active substances, for example insecticides, acaricides, herbicides and fungicides, and also with safeners, fertilizers and/or growth regulators, for example in the form of a ready-mix or tank mix.

[0220] Suitable active ingredients which can be combined with the active ingredients according to the invention in mixed formulations or in a tank mix are, for example, known active ingredients as described for example in Weed Research 26, 441 445 (1986), or “The Pesticide Manual”, 11th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 1997 and in the literature cited therein. For example the following active ingredients may be mentioned as herbicides which are known and which can be combined with the compounds of the formula I (note: the compounds are either named by the “common name” in accordance with the International Organization for Standardization (ISO) or by the chemical names, if appropriate together with a customary code number): acetochlor; acifluorfen; aclonifen; AKH 7088, i.e. [[[1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxy]acetic acid and its methyl ester; alachlor; alloxydim; ametryn; amidosulfuron; amitrol; AMS, i.e. ammonium sulfamate; anilofos; asulam; atrazine; azimsulfurone (DPX-A8947); aziprotryn; barban; BAS 516H, i.e. 5-fluoro-2-phenyl4H-3,1-benzoxazin4-one; benazolin; benfluralin; benfuresate; bensulfuron-methyl; bensulide; bentazone; benzofenap; benzofluor; benzoylprop-ethyl; benzthiazuron; bialaphos; bifenox; bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos; busoxinone; butachlor; butamifos; butenachlor; buthidazole; butralin; butylate; cafenstrole (CH-900); carbetamide; cafentrazone (ICI-A0051); CDM, i.e. 2-chloro-N,N-di-2-propenylacetamide; CDEC, i.e. 2-chloroallyl diethyldithiocarbamate; chlomethoxyfen; chloramben; chlorazifop-butyl, chlormesulon (ICI-A0051); chlorbromuron; chlorbufam; chlorfenac; chlorflurecol-methyl; chloridazon; chlorimuron ethyl; chlornitrofen; chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlorthal-dimethyl; chlorthiamid; cinmethylin; cinosulfuron; clethodim; clodinafop and its ester derivatives (for example clodinafop-propargyl); clomazone; clomeprop; cloproxydim; clopyralid; cumyluron (JC 940); cyanazine; cycloate; cyclosuffamuron (AC 104); cycloxydim; cycluron; cyhalofop and its ester derivatives (for example butyl ester, DEH-112); cyperquat; cyprazine; cyprazole; daimuron; 2,4-DB; dalapon; desmedipham; desmetryn; di-allate; dicamba; dichlobenil; dichlorprop; diclofop and its esters such as diclofop-methyl; diethatyl; difenoxuron; difenzoquat; diflufenican; dimefuron; dimethachlor; dimethametryn; dimethenamid (SAN-582H); dimethazone, clomazon; dimethipin; dimetrasulfuron, dinitramine; dinoseb; dinoterb; diphenamid; dipropetryn; diquat; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 77, i.e. 5-cyano-1-(1,1-dimethylethyl)-N-methyl-1H-pyrazole4-carboxamide; endothal; EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl; ethidimuron; ethiozin; ethofumesate; F5231, i.e. N-[2-chloro4-fluoro-5-[4-(3-fluoropropyl)4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]ethanesulfonamide; ethoxyfen and its 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; fenoxydim; fenuron; flamprop-methyl; flazasulfuron; fluazifop and fluazifop-P and their esters, for example fluazifop-butyl and fluazifop-P-butyl; fluchloralin; flumetsulam; flumeturon; flumiclorac and its esters (for example pentyl ester, S-23031); flumioxazin (S482); flumipropyn; flupoxam (KNW-739); fluorodifen; fluoroglycofen-ethyl; flupropacil (UBIC4243); fluridone; flurochloridone; fluroxypyr; flurtamone; fomesafen; fosamine; furyloxyfen; glufosinate; glyphosate; halosafen; halosulfuron and its esters (for example methyl ester, NC-319); haloxyfop and its esters; haloxyfop-P (=R-haloxyfop) and its esters; hexazinone; imazamethabenz-methyl; imazapyr; imazaquin and salts such as the ammonium salt; imazethamethapyr; imazethapyr; imazosulfuron; ioxynil; isocarbamid; isopropalin; isoproturon; isouron; isoxaben; isoxapyrifop; karbutilate; lactofen; lenacil; linuron; MCPA; MCPB; mecoprop; mefenacet; mefluidid; metamitron; metazachlor; methabenzthiazuron; metham; methazole; methoxyphenone; methyldymron; metobenzuron; metobromuron; metolachlor; metosulam (XRD 511); metoxuron; metribuzin; metsulfuron-methyl; MH; molinate; monalide; monocarbamide dihydrogensulfate; monolinuron; monuron; MT 128, i.e. 6-chloro-N-(3-chloro-2-propenyl)-5-methyl-N-phenyl-3-pyridazin-amine; MT 5950, i.e. N-[3-chloro-4-(1-methylethyl)-phenyl]-2-methyl-pentanamide; naproanilide; napropamide; naptalam; NC 310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole; neburon; nicosulfuron; nipyraclophen; nitralin; nitrofen; nitrofluorfen; norflurazon; orbencarb; oryzalin; oxadiargyl (RP-020630); oxadiazon; oxyfluorfen; paraquat; pebulate; pendimethalin; perfluidone; phenisopham; phenmedipham; picloram; piperophos; piributicarb; pirifenop-butyl; pretilachlor; primisulfuron-methyl; procyazine; prodiamine; profluralin; proglinazine-ethyl; prometon; prometryn; propachlor; propanil; propaquizafop and its esters; propazine; propham; propisochlor; propyzamide; prosulfalin; prosulfocarb; prosulfuron (CGA-152005); prynachlor; pyrazolinate; pyrazon; pyrazosulfuron-ethyl; pyrazoxyfen; pyridate; pyrithiobac (KIH-2031); pyroxofop 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-tefuryl 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; simetryn; SN 106279, i.e. 2-[7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthalenyl]oxy]propanoic acid and its methyl ester; sulfentrazon (FMC-97285, F-6285); sulfazuron; sulfometuron-methyl; sulfosate (ICI-A0224); TCA; tebutam (GCP-5544); tebuthiuron; terbacil; terbucarb; terbuchlor; terbumeton; terbuthylazine; terbutryn; TFH 450, i.e. N,N-diethyl-3-[(2-ethyl-6-methylphenyl)sulfonyl]-1H-1,2,4-triazole-1-carboxamide; thenylchlor (NSK-850); thiazafluron; thiazopyr (Mon-13200); thidiazimin (SN-24085); thifensulfuron-methyl; thiobencarb; tiocarbazil; tralkoxydim; tri-allate; triasulfuron; triazofenamide; tribenuron-methyl; triclopyr; tridiphane; trietazine; trifluralin; triflusulfuron and its esters (for example methyl ester, DPX-46037); trimeturon; tsitodef; vernolate; WL 110547, i.e. 5-phenoxy-1-[3-(trifluoromethyl)phenyl]-1H-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.

[0221] For use, the formulations which are present in commercially available form are, if appropriate, diluted in the customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Products in the form of dusts, granules for soil application or broadcasting and sprayable solutions are usually not further diluted with other inert substances prior to use.

[0222] The application rate of the compounds of the formula I required varies with the external conditions, such as temperature, humidity, the nature of the herbicide used and the like. It can vary within wide limits, for example between 0.001 and 10.0 kg/ha or more of active substance, but it is preferably between 0.005 and 5 kg/ha.

[0223] The examples below illustrate the invention.

A. CHEMICAL EXAMPLES

[0224] 1. Preparation of 2-amino-4-fluoroisopropyl-6-[N-(1-methyl-3-phenoxyprop-1-yl)amino]-1,3,5-triazine (see Table 2, Example No. 368)

[0225] 0.45 g (0.019 mol) of sodium was dissolved in 50 ml of anhydrous methanol. 1.85 g (0.006 mol) of 3-biguanido-1-phenoxybutane hydrochloride were added, followed by 1.3 g (0.010 mol) of ethyl fluoroisobutyrate. The mixture was heated at reflux for 3 h. The solvent was removed under reduced pressure and the residue was taken up in dichloromethane/water and extracted repeatedly. The organic phase was dried over MgSO4 and filtered, and the solvent was removed under reduced pressure. Purification by silica gel column chromatography using ethyl acetate/hepane (1:1) gave 0.45 g (24%) of the title compound.

[0226] 2. Preparation of 2-amino-4-isopropyl-6-{N-[1-methyl-2-(4-chlorobenzyl-oxy)ethyl]amino}-1,3,5-triazine (see Table 1, Example No. 166)

[0227] 1.00 g (0.004 mol) of 2-aminopropyl 4-chlorobenzyl ether hydrochloride was initially charged together with 2.34 g (0.017 mol) of potassium carbonate and 0.73 g (0.004 mol) of 2-amino-4-chloro-4-isopropyl-1,3,5-triazine, and the mixture was heated at reflux for 3 h. The solvent was removed under reduced pressure and the residue was taken up in ethyl acetate/water and extracted repeatedly. The organic phase was dried over MgSO4 and filtered, and the solvent was removed under reduced pressure. Purification by silica gel column chromatography using ethyl acetate/heptane (1:1) gave 1.20 g (89%) of the title compound.

[0228] 3. Preparation of 2-amino-4-isopropyl-6-{N-[2-(3,4-dichlorobenzoyl-oxy)ethyl]amino}-1,3,5-triazine

[0229] 0.5 g (0.0024 mol) of 3,4-dichlorobenzoyl chloride was initially charged in 30 ml of 1,4-dioxane, and 0.47 g (0.0024 mol) of 2-amino-4-isopropyl-6-[N-(2-hydroxyethyl)amino-1,3,5-triazine and 0.483 g (0.005 mol) of triethylamine were added. The mixture was heated at reflux for 4 h. The precipitated solid was filtered off, and the solvent was removed under reduced pressure. The residue was taken up in ethyl acetate/water and extracted repeatedly. The organic phase was dried over MgSO4 and filtered, and solvent was removed under reduced pressure. This gave 0.65 g (73%) of the title compound.

[0230] The examples listed in the tables below were prepared by the methods mentioned above, or they can be obtained by the methods mentioned above.

[0231] The meanings of the abbreviations used in the tables are as follows:

Et =	ethyl	Me =	methyl	c =	cyclo
n =	normal	i =	iso	s =	secondary
t =	tertiary
m.p. =	melting point

[0232] An asymmetrical divalent group Y, such as Y═C(O)O (i.e. —CO—O—) is, in the context of the tables, a group where the linkage point of the group atom shown at the left is attached to the molecular moiety which is shown, in the formula (I), as being to the left of Y.

TABLE 1
Compounds of the formula (Ia) (=formula I where n = 1 and R1, R2, R5,
R7, R9, R10 are each H and aryl = phenyl which is substituted as shown in the table)
10
No.	Z	m	Y	R3	R4	R6	R8	Phys. data
1	2,4-Cl2	0	C(O)O	H	H	Me	i-Propyl	oil
2	2,4-Cl2	0	C(O)O	H	H	Et	i-Propyl	oil
3	2,4-Cl2	0	C(O)O	H	H	H	i-Propyl	oil
4	2,4-Cl2	0	C(O)O	H	H	Me	CF3
5	2,4-F2	0	C(O)O	H	H	Me	i-Propyl	oil
6	2,4-F2	0	C(O)O	H	H	Et	i-Propyl	oil
7	2,4-F2	0	C(O)O	H	H	H	i-Propyl	oil
8	2,4-F2	1	C(O)O	H	H	n-Butyl	CF2CHF2
9	2,5-F2	0	C(O)O	H	H	Me	i-Propyl	oil
10	2,5-F2	0	C(O)O	H	H	Et	i-Propyl	oil
11	2,5-F2	0	C(O)O	H	H	H	i-Propyl	oil
12	2,5-F2	1	C(O)O	H	H	H	CF(CH3)2
13	2,6-F2	0	C(O)O	H	H	Me	i-Propyl	oil
14	2,6-F2	0	C(O)O	H	H	Et	i-Propyl	oil
15	2,6-F2	0	C(O)O	H	H	H	i-Propyl	oil
16	2,6-F2	1	C(O)O	H	H	Me	CF3
17	2-CF3	0	C(O)O	H	H	Et	i-Propyl
18	2-Cl	0	C(O)O	H	H	Me	i-Propyl	oil
19	2-Cl	0	C(O)O	H	H	Et	i-Propyl	oil
20	2-Cl	0	C(O)O	H	H	H	i-Propyl	oil
21	2-Cl	0	C(O)O	H	H	n-Butyl	CF2CHF2
22	2-Cl,4-F	0	C(O)O	H	H	Me	i-Propyl	oil
23	2-Cl,4-F	0	C(O)O	H	H	Et	i-Propyl	oil
24	2-Cl,4-F	0	C(O)O	H	H	H	i-Propyl	oil
25	2-Cl,4-F	0	C(O)O	Me	H	Me	CF(CH3)2
26	2-Cl,4-NO2	0	C(O)O	H	H	Me	i-Propyl	oil
27	2-Cl,4-NO2	0	C(O)O	H	H	Et	i-Propyl	oil
28	2-Cl,4-NO2	0	C(O)O	H	H	H	i-Propyl	oil
29	2-Cl,4-NO2	0	C(O)O	H	H	1-Butyl	i-Propyl
30	2-Cl,5-NO2	0	C(O)O	H	H	Me	i-Propyl	oil
31	2-Cl,5-NO2	0	C(O)O	H	H	Et	i-Propyl	oil
32	2-Cl,5-NO2	0	C(O)O	H	H	H	i-Propyl	oil
33	2-Cl,5-NO2	0	C(O)O	H	H	Me	CF(CH3)2
34	2-F	0	C(O)O	H	H	Me	i-Propyl	oil
35	2-F	0	C(O)O	H	H	Et	i-Propyl	oil
36	2-F	0	C(O)O	H	H	H	i-Propyl	oil
37	2-F	0	C(O)O	Me	H	CH2OEt	CF(CH3)2
38	2-F,3-CF3	0	C(O)O	H	H	Et	i-Propyl
39	2-F,4-CF3	0	C(O)O	H	H	Et	i-Propyl
40	2-F,5-CF3	0	C(O)O	H	H	Et	i-Propyl
41	2-Me	0	C(O)O	H	H	Me	i-Propyl	oil
42	2-Me	0	C(O)O	H	H	Et	i-Propyl	oil
43	2-Me	0	C(O)O	H	H	H	i-Propyl	oil
44	2-Me	2	C(O)O	H	H	CH2-c-Propyl	CF(CH3)2
45	2-OAc	0	C(O)O	H	H	Me	i-Propyl	oil
46	2-OAc	0	C(O)O	H	H	Et	i-Propyl	oil
47	2-OAc	0	C(O)O	H	H	H	i-Propyl	oil
48	2-OAc	1	C(O)O	Me	H	c-Pentyl	CHFCH3
49	3,4-Cl2	0	C(O)O	H	H	Me	i-Propyl	oil
50	3,4-Cl2	0	C(O)O	H	H	Et	i-Propyl	oil
51	3,4-Cl2	0	C(O)O	H	H	H	i-Propyl	oil
52	3,4-Cl2	0	C(O)O	H	H	s-Butyl	CHFCF3
53	3,5-(CF3)2	0	C(O)O	H	H	Et	i-Propyl
54	3,5-Cl2	0	C(O)O	H	H	Me	i-Propyl	oil
55	3,5-Cl2	0	C(O)O	H	H	Et	i-Propyl	oil
56	3,5-Cl2	0	C(O)O	H	H	H	i-Propyl	oil
57	3,5-Cl2	0	C(O)O	H	H	CH2OMe	CHFCH3
58	3,5-F2	1	SO2	Me	H	Me	CF2CHF2
59	3,5-F2	2	0	H	H	Et	CF2CHF2
60	3,5-F2	1	0	H	H	c-Butyl	CF2CHF2
61	3,5-F2	1	0	H	H	H	CF2CHF2
62	3,5-Me2	1	C(O)O	Et	H	H	CF2CHF2
63	3,5-Me2	1	0	H	H	Me	i-Propyl	m.p. 80° C.
64	3,5-Me2	1	0	H	H	Me	CF(CH3)2	resin
65	3,5-Me2	1	0	Me	H	Et	CHFCH3
66	3,5-Me2	1	0	H	H	c-Butyl	CF2CHF2
67	3,5-Me2	1	0	H	H	c-Pentyl	CF(CH3)2
68	3,5-Me2	1	0	Et	H	H	CF2CHF2
69	3,5-(OMe)2	1	C(O)O	Me	H	H	CHFCH3
70	3,5-(OMe)2	1	0	H	H	Me	CF3
71	3,5-(OMe)2	1	S	Me	H	Et	CF(CH3)2
72	3,5-(OMe)2	1	SO2	H	H	c-Butyl	CHFCH3
73	3,5-(OMe)2	1	O	H	H	c-Pentyl	i-Propyl
74	3,5-(OMe)2	1	SO2	Me	H	H	CHFCH3
75	3-Br	1	O	H	H	Me	i-Propyl	resin
76	3-Br	1	O	H	H	Me	CF(CH3)2	m.p. 101° C.
77	3-Br	1	0	H	H	Me	CF2CHF2	m.p. 128° C.
78	3-CF3	0	C(O)O	H	H	Me	i-Propyl	oil
79	3-CF3	0	C(O)O	H	H	Et	i-Propyl	oil
80	3-CF3	0	C(O)O	H	H	H	i-Propyl	oil
81	3-CF3	1	SO2	H	H	Et	CF3
82	3-CF3	1	O	H	H	c-Propyl	CHFCH3
83	3-CF3	2	O	H	H	c-Butyl	i-Propyl
84	3-Cl	0	C(O)O	H	H	Me	i-Propyl	oil
85	3-Cl	0	C(O)O	H	H	Et	i-Propyl	oil
86	3-Cl	0	C(O)O	H	H	H	i-Propyl	oil
87	3-Cl	0	C(O)O	H	H	CF3	CF2CHF2
88	3-Cl	1	C(O)O	H	H	H	CF(CH3)2
89	3-Cl	1	O	H	H	Me	i-Propyl	resin
90	3-Cl	1	O	H	H	Me	CF(CH3)2	resin
91	3-Cl	1	O	H	H	Me	CF2CHF2	m.p. 103° C.
92	3-Cl	1	O	H	H	Et	CF3
93	3-Cl	1	SO2	H	H	c-Butyl	CF(CH3)2
94	3-Cl	1	SO2	H	H	c-Pentyl	CF2CHF2
95	3-Cl	1	SO2	H	H	H	CF(CH3)2
96	3-Cl,5-Me	1	O	c-Propyl	H	Et	CF2CHF2
97	3-Cl,5-Me	1	O	H	H	c-Propyl	CF3
98	3-Cl,5-Me	1	O	H	H	c-Butyl	CHFCH3
99	3-F	0	C(O)O	H	H	Me	i-Propyl	oil
100	3-F	0	C(O)O	H	H	Et	i-Propyl	oil
101	3-F	0	C(O)O	H	H	H	i-Propyl	oil
102	3-F	0	C(O)O	H	H	i-Propyl	i-Propyl
103	3-F	1	C(O)O	c-Propyl	H	H	i-Propyl
104	3-F	1	O	H	H	Me	i-Propyl
105	3-F	2	O	H	H	Et	i-Propyl
106	3-F	2	O	H	H	c-Butyl	i-Propyl
107	3-F	2	O	c-Propyl	H	H	i-Propyl
108	3-F,4-CF3	0	C(O)O	H	H	Et	i-Propyl
109	3-F,5-CF3	0	C(O)O	H	H	Et	i-Propyl
110	3-F,5-Me	2	O	H	H	Me	i-Propyl
111	3-F,5-Me	1	O	H	H	Et	CHFCH3
112	3-F,5-Me	2	O	H	H	c-Propyl	i-Propyl
113	3-F,5-Me	1	S	H	H	c-Butyl	CF(CH3)2
114	3-F,5-OMe	2	S	H	H	Me	CF2CHF2
115	3-F,5-OMe	1	O	H	H	Et	CF(CH3)2
116	3-F,5-OMe	2	S	H	H	c-Propyl	CF2CHF2
117	3-F,5-OMe	1	SO2	H	H	c-Butyl	CF3
118	3-Me	1	C(O)O	H	H	H	CF3
119	3-Me	1	O	H	H	Me	i-Propyl	resin
120	3-Me	1	O	H	H	Me	CF(CH3)2	m.p. 112° C.
121	3-Me	1	O	H	H	Me	CF2CHF2	resin
122	3-Me	1	O	H	H	Et	CF(CH3)2
123	3-Me	1	O	H	H	c-Butyl	CF3
124	3-Me	1	O	H	H	c-Pentyl	CF2CHF2
125	3-Me	1	O	H	H	H	CF3
126	3-Me,4-F	2	O	H	H	Me	CHFCH3
127	3-Me,4-F	2	SO2	H	H	Et	CF(CH3)2
128	3-Me,4-F	1	O	H	H	c-Propyl	CHFCH3
129	3-Me,4-F	1	O	H	H	c-Butyl	CF(CH3)2
130	3-Me,4-F	1	O	c-Propyl	H	H	CF(CH3)2
131	3-OCF3	0	C(O)O	H	H	Me	i-Propyl	oil
132	3-OCF3	0	C(O)O	H	H	Et	i-Propyl	oil
133	3-OCF3	0	C(O)O	H	H	H	i-Propyl	oil
134	3-OCF3	0	C(O)O	H	H	Me	CF(CH3)2
135	3-OEt	2	O	c-Propyl	H	Me	CF(CH3)2
136	3-OEt	2	S	H	H	Et	i-Propyl
137	3-OEt	2	O	Et	H	c-Propyl	CF(CH3)2
138	3-OEt	1	O	Me	H	c-Butyl	CF3
139	3-OMe	1	C(O)O	H	H	H	i-Propyl
140	3-OMe	1	S	H	H	Me	CF(CH3)2
141	3-OMe	1	O	H	H	Et	CF3
142	3-OMe	1	O	H	H	c-Butyl	i-Propyl
143	3-OMe	1	O	c-Propyl	H	c-Pentyl	CHFCH3
144	3-OMe	1	O	H	H	H	i-Propyl
145	3-OMe,5-Cl	2	0	H	H	Et	CHFCH3
146	3-OMe,5-Cl	2	S	H	H	c-Butyl	CHFCH3
147	3-OMe,5-Cl	2	S	Me	Me	H	CHFCH3
148	4-Br	0	C(O)O	H	H	Me	i-Propyl	oil
149	4-Br	0	C(O)O	H	H	Et	i-Propyl	oil
150	4-Br	0	C(O)O	H	H	H	i-Propyl	oil
151	4-Br	1	C(O)O	Me	H	c-Pentyl	CHFCH3
152	4-Br	1	O	H	H	Me	i-Propyl	m.p. 82° C.
153	4-Br	1	O	H	H	Me	CF(CH3)2	resin
154	4-Br	1	O	H	H	Me	CF2CHF2	m.p. 114° C.
155	4-CF3	0	C(O)O	H	H	Me	i-Propyl	oil
156	4-CF3	0	C(O)O	H	H	Et	i-Propyl	oil
157	4-CF3	0	C(O)O	H	H	H	i-Propyl	oil
158	4-CF3	0	C(O)O	H	H	Me	i-Propyl	oil
159	4-CF3	0	C(O)O	H	H	Et	i-Propyl	oil
160	4-CF3	0	C(O)O	H	H	H	i-Propyl	oil
161	4-CF3	0	C(O)O	H	H	CH2-c-Butyl	CF3
162	4-Cl	0	C(O)O	H	H	Me	i-Propyl	oil
163	4-Cl	0	C(O)O	H	H	Et	i-Propyl	oil
164	4-Cl	0	C(O)O	H	H	H	i-Propyl	oil
165	4-Cl	0	C(O)O	H	H	CH2F	CHFCH3
166	4-Cl	1	O	H	H	Me	i-Propyl	resin
167	4-Cl	1	O	H	H	Me	CF(CH3)2	resin
168	4-Cl	1	0	H	H	Me	CF2CHF2	m.p. 104° C.
169	4-F	0	C(O)O	H	H	Me	i-Propyl	oil
170	4-F	0	C(O)O	H	H	Et	i-Propyl	oil
171	4-F	0	C(O)O	H	H	H	i-Propyl	oil
172	4-F	1	C(O)O	H	H	t-Butyl	i-Propyl
173	4-F,5-CF3	0	C(O)O	H	H	Et	i-Propyl
174	4-I	0	C(O)O	H	H	Me	i-Propyl	oil
175	4-I	0	C(O)O	H	H	Et	i-Propyl	oil
176	4-I	0	C(O)O	H	H	H	i-Propyl	oil
177	4-I	0	C(O)O	H	H	H	CF(CH3)2
178	4-Me	0	C(O)O	H	H	Me	i-Propyl	oil
179	4-Me	0	C(O)O	H	H	Et	i-Propyl	oil
180	4-Me	0	C(O)O	H	H	H	i-Propyl	oil
181	4-Me	0	C(O)O	H	H	i-Propyl	i-Propyl
182	4-Me	1	O	H	H	Me	i-Propyl	resin
183	4-Me	1	O	H	H	Me	CF(CH3)2	resin
184	4-n-Bu	0	C(O)O	H	H	Me	i-Propyl	oil
185	4-n-Bu	0	C(O)O	H	H	Et	i-Propyl	oil
186	4-n-Bu	0	C(O)O	H	H	H	i-Propyl	oil
187	4-n-Bu	2	C(O)O	H	H	H	CF(CH3)2
188	4-OCF3	0	C(O)O	H	H	Me	i-Propyl	oil
189	4-OCF3	0	C(O)O	H	H	Et	i-Propyl	oil
190	4-OCF3	0	C(O)O	H	H	H	i-Propyl	oil
191	4-OCF3	0	C(O)O	H	H	Me	CF(CH3)2
192	4-t-Bu	0	C(O)O	H	H	Me	i-Propyl	oil
193	4-t-Bu	0	C(O)O	H	H	Et	i-Propyl	oil
194	4-t-Bu	0	C(O)O	H	H	H	i-Propyl	oil
195	4-t-Bu	0	C(O)O	Me	H	s-Butyl	CF(CH3)2
196	H	0	C(O)O	H	H	Me	i-Propyl	oil
197	H	0	C(O)O	H	H	Et	i-Propyl	oil
198	H	0	C(O)O	H	H	H	i-Propyl	oil
199	H	0	C(O)O	H	H	Me	CF(CH3)2
200	H	1	O	H	H	Me	i-Propyl	m.p. 104° C.
201	H	1	O	H	H	Me	CF(CH3)2	resin
202	H	1	O	H	H	Me	CF2CHF2	m.p. 118° C.
203	H	1	O	Me	H	Me	CHFCH3
204	H	1	SO2	Me	H	Et	CHFCH3
205	H	1	O	Me	H	c-Butyl	CF(CH3)2
206	H	1	O	Me	Me	H	CF(CH3)2

[0233]

TABLE 2
Compounds of the formula (Ib) (=formula I where n = 2, R1, R2, R3, R5,
R7, R9, R10 are each hydrogen and aryl = phenyl which is
substituted as shown in the table)
11
No.	Z	m	Y	R3	R4	R6	R8	Phys. data
207	3,5-F2	0	O	H	H	Me	CF(CH3)2	resin
208	3,5-(OMe)2	0	O	H	H	t-Butyl	i-Propyl
209	3-Cl	0	O	H	H	Me	i-Propyl	resin
210	3-F	0	O	Et	Et	H	CF2CHF2
211	3-Me	0	O	H	H	c-Propyl	CF2CHF2
212	3-Me,4-F	0	O	H	H	Me	CF(CH3)2	resin
213	3-OMe	0	O	H	H	Me	i-Propyl	resin
214	H	0	O	Me	Me	H	i-Propyl	oil
215	3,4,5-Cl3	1	O	H	H	c-Pentyl	CHFCH3
216	3,5-F2	0	O	H	H	Et	CF2CHF2	resin
217	3,5-Me2	0	O	H	H	Et	CF(CH3)2	resin
218	3-CF3	1	C(O)O	H	H	Me	CHFCH3
219	3-Cl	0	O	H	H	c-Propyl	CF2CHF2
220	3-Cl	0	O	H	H	Et	CHFCH3	resin
221	3-Cl,5-Me	1	O	H	H	CH2-cButyl	i-Propyl
222	3-F	0	O	H	H	Et	CF(CH3)2	resin
223	3-F	0	O	Et	H	H	CHFCH3
224	3-Me	0	O	Me	Me	H	i-Propyl
225	3-Me	0	O	Me	H	Me	CF(CH3)2	resin
226	3-Me,4-F	0	O	H	H	Et	CHFCH3	resin
227	3-Me,4-F	0	O	H	H	c-Propyl	CF2CHF2	resin
228	3-OMe	0	O	H	H	Et	CF2CHF2	resin
229	3-OMe,5-Cl	1	O	H	H	n-Butyl	CF2CHF2
230	H	0	O	Me	H	Me	CF(CH3)2
231	H	0	O	H	H	Et	i-Propyl	resin
232	3,5-F2	0	O	H	H	c-Propyl	CF2CHF2
233	3,5-(OEt)2	1	S	H	H	CH2OMe	CHFCH3
234	3-Cl	0	O	Me	H	Me	CHFCH3	resin
235	3-F	0	O	Et	Et	H	CF(CH3)2
236	3-Me	0	O	H	H	c-Propyl	CF(CH3)2	resin
237	3-Me	0	SO2	H	H	i-Propyl	i-Propyl
238	3-OMe	0	O	H	H	c-Butyl	CHFCH3
239	H	0	O	H	H	c-Butyl	CHFCH3	resin
240	3,5-F2	0	O	H	H	c-Propyl	CHFCH3
241	3,5-(OEt)2	0	O	H	H	CH2-cButyl	CF2CHF2
242	3-Cl	0	O	Me	H	Me	CF(CH3)2	resin
243	3-F	0	O	Et	Et	H	i-Propyl
244	3-Me	0	O	H	H	c-Propyl	i-Propyl	resin
245	3-Me	0	O	H	H	Et	CF(CH3)2	resin
246	3-OMe	0	O	H	H	c-Butyl	CF(CH3)2
247	H	0	O	H	H	c-Butyl	CF(CH3)2
248	3,5-Cl2	0	O	H	Et	i-Propyl	i-Propyl
249	3,5-(OEt)2	1	O	H	H	n-Butyl	CF2CHF2
250	3-Cl	0	O	Me	Me	H	CHFCH3
251	3-F	0	O	H	H	c-Butyl	CF(CH3)2
252	3-F,5-OMe	1	O	H	H	s-Butyl	i-Propyl
253	3-Me	0	O	H	H	Me	CF(CH3)2	resin
254	3-OEt	1	C(O)O	H	H	CH2-cButyl	i-Propyl
255	H	0	O	H	H	c-Propyl	CHFCH3	resin
256	3,4,5-Cl3	0	O	H	H	CF3	CHFCH3
257	3,5-Cl2	0	O	H	H	CH2OEt	CF(CH3)2
258	3,5-Cl2	1	SO2	H	H	Me	CF3
259	3,5-Me2	0	O	H	H	c-Pentyl	CHFCH3
260	3,5-(OEt)2	0	O	H	H	Me	CHFCF3
261	3,5-(OEt)2	0	C(O)O	H	H	i-Propyl	i-Propyl
262	3-Cl	0	O	H	H	c-Butyl	CHFCH3
263	3-Cl	0	O	Me	Me	H	i-Propyl	resin
264	3-Cl	0	O	Me	Me	H	CF(CH3)2	resin
265	3-F	0	O	H	H	c-Propyl	CF(CH3)2
266	3-F	0	O	H	H	c-Propyl	CF2CHF2
267	3-F	0	O	H	H	c-Butyl	i-Propyl
268	3-F,5-Me	0	SO2	H	H	Me	CF(CH3)2
269	3-F,5-Me	0	O	H	H	n-Butyl	CF2CHF2
270	3-F,5-OMe	0	C(O)O	H	H	c-Pentyl	CF3
271	3-Me	0	O	Me	H	H	i-Propyl	resin
272	3-Me	0	O	Me	H	H	CF2CHF2	resin
273	3-Me	0	O	H	H	Me	i-Propyl	resin
274	3-Me,4-F	0	O	H	H	c-Butyl	CHFCH3	resin
275	3-OEt	2	O	H	H	CH2F	i-Propyl
276	3-aEt	0	O	H	H	CH2-c-Propyl	CF3
277	3-Ph	1	SO2	H	Me	t-Butyl	i-Propyl
278	H	0	O	H	H	c-Propyl	i-Propyl	resin
279	H	0	O	H	H	c-Propyl	CF(CH3)2	resin
280	H	0	O	H	H	Me	CF3
281	3,5-F2	0	O	H	H	Me	i-Propyl	resin
282	3,5-Me2	0	O	H	H	Me	CF(CH3)2	m.p. 131° C.
283	3,5-(OMe)2	0	C(O)O	H	H	s-Butyl	CHFCF3
284	3-Cl	0	O	H	H	c-Propyl	i-Propyl	resin
285	3-Cl	0	O	Me	H	Me	CF2CHF2	resin
286	3-Cl	0	O	H	H	CH2-c-Propyl	CF(CH3)2
287	3-F	0	O	Et	Et	H	CHFCH3
288	3-F	0	O	H	H	CH2-c-Butyl	CF3
289	3-Me	0	O	H	H	c-Propyl	CHFCH3	resin
290	3-Me	0	O	Me	Me	H	CHFCH3
291	3-Me,4-F	0	O	H	H	Me	i-Propyl	resin
292	3-Me,4-F	0	O	H	H	c-Propyl	i-Propyl	resin
293	3-OMe	0	O	H	H	c-Butyl	CF2CHF2
294	3-OMe,5-Cl	0	O	H	H	Me	i-Propyl	resin
295	H	0	O	H	H	c-Butyl	CF2CHF2
296	H	0	O	Me	H	Me	CF2CHF2
297	3,5-F2	0	O	H	H	Me	CF2CHF2	resin
298	3,5-(OMe)2	0	O	H	Me	CF3	CF2CHF2
299	3-Cl	0	O	H	H	Me	CF(CH3)2	resin
300	3-F	0	O	H	H	Me	i-Propyl	resin
301	3-Me	0	O	H	H	c-Butyl	i-Propyl	resin
302	3-Me,4-F	0	O	H	H	Me	CHFCH3
303	3-OMe	0	O	H	H	Me	CF(CH3)2	resin
304	H	0	O	Me	Me	H	CF(CH3)2	resin
305	3,5-F2	0	O	H	H	Et	i-Propyl	resin
306	3,5-(OMe)2	0	O	H	H	CH2F	CHFCH3
307	3-Cl	0	O	H	H	Me	CF2CHF2	resin
308	3-F	0	O	H	H	Me	CF(CH3)2	resin
309	3-Me	0	O	H	H	c-Butyl	CF(CH3)2	resin
310	3-Me,4-F	0	O	H	H	Me	CF2CHF2	resin
311	3-OMe	0	O	H	H	Me	CF2CHF2	resin
312	H	0	O	Me	Me	H	CHFCH3	resin
313	3,5-Cl2	0	SO2	H	H	CH2OMe	CHFCH3
314	3,5-(OEt)2	0	O	H	H	CH2OEt	CHFCH3
315	3-Cl	0	O	H	H	c-Butyl	CF2CHF2
316	3-F	0	O	H	H	c-Propyl	CHFCH3
317	3-F.5-Me	0	O	H	H	i-Propyl	i-Propyl
318	3-Me	0	O	Me	H	H	CF(CH3)2	resin
319	3-Me,4-F	0	O	H	H	c-Butyl	CF2CHF2
320	3-Ph	0	O	H	H	CF3	CF2CHF2
321	3,5-F2	0	O	H	H	c-Propyl	i-Propyl
322	3,5-(OEt)2	0	S	H	H	CH2F	CHFCF3
323	3-Cl	0	O	Me	Me	H	CF2CHF2
324	3-F	0	O	H	H	c-Butyl	CHFCH3
325	3-F,5-OMe	0	O	H	H	1-Butyl	CF2CHF2
326	3-Me	0	O	H	H	Me	CF2CHF2	resin
327	3-OEt	1	0	H	Et	CH2OMe	CF2CHF2
328	H	0	O	H	H	c-Propyl	CF2CHF2
329	3,5-Me2	0	O	H	H	Me	CF2CHF2	resin
330	3-Cl	0	O	H	H	c-Propyl	CF(CH3)2	resin
331	3-Cl,5-Me	1	C(O)O	H	Me	CH2F	CF(CH3)2
332	3-F	0	O	H	H	H	i-Propyl
333	3-Me	0	O	Me	Me	H	CF2CHF2
334	3-Me,4-F	0	O	H	H	c-Propyl	CF(CH3)2	resin
335	3-OMe,5-Cl	0	O	H	H	Me	CF(CH3)2	resin
336	H	0	O	H	H	Me	i-Propyl	resin
337	3,4,5-Cl3	0	S	H	H	s-Butyl	CF(CH3)2
338	3,5-F2	0	O	H	H	c-Propyl	CF(CH3)2
339	3,5-Me2	0	O	H	H	Me	i-Propyl	resin
340	3,5-Me2	0	O	H	H	Et	i-Propyl	resin
341	3,5-Me2	0	O	H	H	Et	CHFCH3	resin
342	3,5-(OEt)2	1	O	H	H	CH2-c-Propyl	i-Propyl
343	3-CF3	0	S	H	H	Me	CF(CH3)2
344	3-Cl	0	O	H	H	c-Propyl	CHFCH3	resin
345	3-Cl	0	O	H	H	c-Butyl	i-Propyl
346	3-Cl	0	O	Me	H	Me	i-Propyl	resin
347	3-Cl	0	O	H	H	Et	CF2CHF2	resin
348	3-Cl,5-Me	0	O	H	Et	CH2-c-Propyl	CF3
349	3-Cl,5-Me	0	O	H	H	CH2OMe	CF2CHF2
350	3-F	0	O	H	H	c-Butyl	CF2CHF2
351	3-F	0	O	H	H	Et	CHFCH3	resin
352	3-F	2	0	H	H	H	CF(CH3)2
353	3-F	0	O	H	H	H	CF2CHF2
354	3-F,5-OMe	0	O	H	H	CF3	CHFCH3
355	3-Me	0	O	Me	Me	H	CF(CH3)2
356	3-Me	0	O	Me	H	Me	i-Propyl	oil
357	3-Me	0	O	Me	H	Me	CHFCH3	oil
358	3-Me	0	O	H	H	Et	i-Propyl	resin
359	3-Me,4-F	0	O	H	H	Et	CF2CHF2
360	3-Me,4-F	0	O	H	H	c-Propyl	CHFCH3	resin
361	3-Me,4-F	0	O	H	H	c-Butyl	i-Propyl
362	3-OMe	0	O	H	H	c-Butyl	i-Propyl
363	3-OMe	0	O	H	Me	n-Butyl	CF2CHF2
364	3-OMe,5-Cl	0	O	H	H	Me	CF2CHF2	resin
365	3-Ph	1	0	H	H	c-Pentyl	CHFCH3
366	H	0	O	H	H	c-Butyl	i-Propyl	resin
367	H	0	O	Me	H	Me	CHFCH3
368	H	0	O	H	H	Me	CF(CH3)2	resin
369	H	0	O	H	H	Et	CF(CH3)2	resin
370	3,5-F2	0	O	H	H	Et	CF(CH3)2	resin
371	3-CF3	0	O	H	H	CH2OEt	CF(CH3)2
372	3-Cl	0	O	H	H	Et	i-Propyl	resin
373	3-F	0	O	H	H	Me	CF2CHF2	resin
374	3-Me	0	O	H	H	c-Butyl	CHFCH3	resin
375	3-Me,4-F	0	O	H	H	Et	i-Propyl	resin
376	3-OMe	0	O	H	H	Et	i-Propyl	resin
377	H	0	O	Me	Me	H	CF2CHF2
378	3,5-F2	0	O	H	H	Et	CHFCH3	resin
379	3-CF3	0	O	H	H	Me	CF3
380	3-Cl	0	O	H	H	Et	CF(CH3)2	resin
381	3-F	0	O	H	H	Et	i-Propyl	resin
382	3-Me	0	O	H	H	c-Butyl	CF2CHF2
383	3-Me,4-F	0	O	H	H	Et	CF(CH3)2	resin
384	3-OMe	0	O	H	H	Et	CF(CH3)2	resin
385	H	0	O	Me H	Me	i-Propyl
386	3,4,5-Cl3	0	O	H	H	t-Butyl	CF3
387	3,5-Me2	0	O	H	H	Et	CF2CHF2	resin
388	3-Cl	0	O	H	H	c-Butyl	CF(CH3)2	resin
389	3-F	0	O	H	H	c-Propyl	i-Propyl
390	3-F,5-Me	2	O	H	H	CH2OEt	CHFCH3
391	3-Me	0	O	Me	H	Me	CF2CHF2
392	3-Me,4-F	0	O	H	H	c-Butyl	CF(CH3)2
393	3-Ph	0	SO2	H	H	5-Butyl	CF(CH3)2
394	H	0	O	H	H	Et	CF2CHF2	resin
395	4-F	0	O	H	H	c-Butyl	i-Propyl	resin
396	4-F	0	O	H	H	c-Butyl	CF(CH3)2	resin
397	4-F	0	O	H	H	c-Butyl	CHFCH3	resin
398	4-F	0	O	H	H	c-Butyl	CF2CHF2	resin
399	3,4-F2	0	O	H	H	c-Butyl	i-Propyl	resin
400	3,4-F2	0	O	H	H	c-Butyl	CF(CH3)2	resin
401	3,4-F2	0	O	H	H	c-Butyl	CHFCH3	resin
402	3,4-F2	0	O	H	H	c-Butyl	CF2CHF2	resin
403	H	0	O	H	H	c-Butyl	CCl(CH3)2	resin
404	3-Me	0	O	H	H	c-Butyl	CCl(CH3)3	resin
405	H	0	O	H	H	c-Butyl	Me	resin
406	3-Me	0	O	H	H	c-Butyl	Et	resin
407	H	0	O	H	H	c-Butyl	Me	resin
408	3-Me	0	O	H	H	c-Butyl	Et	resin
409	3-Me	0	O	H	H	c-Butyl	CF2CF3	resin
410	4-F	0	O	H	H	c-Propyl	i-Propyl	resin
411	4-F	0	O	H	H	c-Propyl	CF(CH3)2	resin
412	4-F	0	O	H	H	c-Propyl	CHFCH3	resin
413	4-F	0	O	H	H	c-Propyl	CF2CHF2	resin
414	3,4-F2	0	O	H	H	c-Propyl	i-Propyl
415	3,4-F2	0	O	H	H	c-Propyl	CF(CH3)2
416	3,4-F2	0	O	H	H	c-Propyl	CHFCH3
417	3,4-F2	0	O	H	H	c-Propyl	CF2CHF2
418	H	0	O	H	H	c-Propyl	CCl(CH3)2	resin
419	3-Me	0	O	H	H	c-Propyl	CCl(CH3)3	resin
420	H	0	O	H	H	c-Propyl	Me	resin
421	3-Me	0	O	H	H	c-Propyl	Et	resin
422	H	0	O	H	H	c-Propyl	Me	resin
423	3-Me	0	O	H	H	c-Propyl	Et	resin
424	3-Me	0	O	H	H	c-Propyl	CF2CF3	resin
425	3-Me	0	O	H	H	Et	Me	resin
426	3-Me	0	O	H	H	Et	Et	resin
427	3-Me	0	O	H	H	Et	CF2CF3	resin
428	4-F	1	O	H	H	Et	CF(CH3)2
429	4-F	1	O	H	H	Et	CHFCH3
430	3-Cl	1	O	H	H	Et	CF(CH3)2
431	3-Cl	1	O	H	H	Et	CHFCH3
432	3-Me	1	O	H	H	Et	CF(CH3)2
433	3-Me	1	O	H	H	Et	CHFCH3
434	3-Me,4-F	1	O	H	H	Et	CF(CH3)2
435	3-Me,4-F	1	O	H	H	Et	CHFCH3
436	3,5-Me2	1	O	H	H	Et	CF(CH3)2
437	3,5-Me2	1	O	H	H	Et	CHFCH3
438	3-F	1	O	H	H	Et	CF(CH3)2
439	3-F	1	O	H	H	Et	CHFCH3
440	H	1	O	H	H	Et	CF(CH3)2
441	H	1	O	H	H	Et	CHFCH3
442	3-Cl,5-F	1	O	H	H	Et	CF(CH3)2
443	3-Cl,5-F	1	O	H	H	Et	CHFCH3
444	3-Cl	2	O	H	H	Et	CF(CH3)2
445	3-Cl	2	O	H	H	Et	CHFCH3
446	3-Me	2	O	H	H	Et	CF(CH3)2
447	3-Me	2	O	H	H	Et	CHFCH3
448	3-Me,4-F	2	O	H	H	Et	CF(CH3)2
449	3-Me,4-F	2	O	H	H	Et	CHFCH3
450	3,5-Me2	2	O	H	H	Et	CF(CH3)2
451	3,5-Me2	2	O	H	H	Et	CHFCH3
452	3-F	2	O	H	H	Et	CF(CH3)2
453	3-F	2	O	H	H	Et	CHFCH3
454	H	2	O	H	H	Et	CF(CH3)2
455	H	2	O	H	H	Et	CHFCH3
456	3-Cl	0	O	Et	Et	H	CF(CH3)2	resin
457	3-Cl	0	O	Et	Et	H	CHFCH3	resin
458	3-Me	0	O	H	H	Me	Me	resin
459	3-Me	0	O	H	H	Me	Et	resin
460	3-Me	0	O	H	H	Me	CF2CF3	resin
461	4-F	1	O	H	H	Me	CF(CH3)2
462	4-F	1	O	H	H	Me	CHFCH3
463	3-Cl	1	O	H	H	Me	CF(CH3)2
464	3-Ci	1	O	H	H	Me	CHFCH3
465	3-Me	1	O	H	H	Me	CF(CH3)2
466	3-Me	1	O	H	H	Me	CHFCH3
467	3-Me,4-F	1	O	H	H	Me	CF(CH3)2
468	3-Me,4-F	1	O	H	H	Me	CHFCH3
469	3,5-Me2	1	O	H	H	Me	CF(CH3)2
470	3,5-Me2	1	O	H	H	Me	CHFCH3
471	3-F	1	O	H	H	Me	CF(CH3)2
472	3-F	1	O	H	H	Me	CHFCH3
473	H	1	O	H	H	Me	CF(CH3)2
474	H	1	O	H	H	Me	CHFCH3
475	3-Cl,5-F	1	O	H	H	Me	CF(CH3)2
476	3-Cl,5-F	1	O	H	H	Me	CHFCH3
477	3-Cl	2	O	H	H	Me	CF(CH3)2
478	3-Cl	2	O	H	H	Me	CHFCH3
479	3-Me	2	O	H	H	Me	CF(CH3)2
480	3-Me	2	O	H	H	Me	CHFCH3
481	3-Me,4-F	2	O	H	H	Me	CF(CH3)2
482	3-Me,4-F	2	O	H	H	Me	CHFCH3
483	3,5-Me2	2	O	H	H	Me	CF(CH3)2
484	3,5-Me2	2	O	H	H	Me	CHFCH3
485	3-F	2	O	H	H	Me	CF(CH3)2
486	3-F	2	O	H	H	Me	CHFCH3
487	H	2	O	H	H	Me	CF(CH3)2
488	H	2	O	H	H	Me	CHFCH3

[0234]

TABLE 3
Compounds of the formula (Ic) (=formula I where n = 3;
R1, R2, R5, R7, R9, R10 are each hydrogen and
aryl = phenyl which is substituted as shown in the table)
12
No.	Z	m	Y	R3	R4	R6	R8	Phys. data
489	3-F	0	O	H	H	Me	CHFCH3
490	H	0	O	H	H	Et	CF(CH3)2	resin
491	3-Me	0	O	H	Me	c-Propyl	i-Propyl
492	3-Cl	0	O	H	H	c-Propyl	CF2CHF2
493	3-F	0	O	H	H	c-Butyl	CHFCH3
494	3,5-Me2	0	O	H	H	t-Butyl	i-Propyl
495	3-Cl,5-Me	2	SO2	H	H	Me	CHFCF3
496	3-F,5-Me	0	O	H	H	CH2F	CF(CH3)2
497	H	0	O	H	H	Et	CF2CHF2
498	3-F	0	O	H	H	c-Propyl	CF(CH3)2
499	3,5-Me2	0	O	H	H	CH2F	CHFCH3
500	3-F,5-OMe	0	O	H	H	CH2-c-Butyl	i-Propyl
501	H	0	O	H	H	Me	CF(CH3)2	resin
502	3-Me	0	O	H	H	Me	CF(CH3)2	resin
503	3-Me	0	O	H	H	Et	CF2CHF2
504	3-Cl	0	O	H	H	Et	CF2CHF2
505	H	0	O	H	H	c-Butyl	CF(CH3)2
506	3-Me	0	O	H	H	c-Butyl	CF(CH3)2
507	3,5-(OMe)2	1	S	H	Et	H	CF(CH3)2
508	3,5-F2	0	O	H	H	c-Pentyl	CHFCH3
509	3-CF3	2	S	H	H	i-Propyl	i-Propyl
510	H	0	O	H	H	Et	i-Propyl	resin
511	3-Cl	0	O	H	H	H	CHFCH3
512	3,5-Me2	0	O	H	H	s-Butyl	CHFCF3
513	3-F,5-Me	1	0	H	H	CF3	CHFCH3
514	3-Me	0	O	H	H	Et	CF(CH3)2	resin
515	3-F	0	O	H	H	c-Propyl	CF2CHF2
516	3,5-(OMe)2	1	C(O)O	H	Et	CH2-c-Butyl	CF3
517	3-F,5-OMe	0	O	H	H	CH2OEt	CHFCH3
518	H	0	O	H	H	Me	CHFCH3	resin
519	3-Me	0	O	H	H	Me	CF2CHF2
520	3-Cl	0	O	H	H	Et	i-Propyl
521	3-F	0	O	H	H	Et	CF(CH3)2
522	H	0	O	H	H	c-Butyl	CHFCH3
523	3-Me	0	O	H	H	H	CF2CHF2
524	3,5-F2	1	0	H	Me	Me	CF3
525	3-OMe,5-Cl	0	O	H	H	t-Butyl	i-Propyl
526	3-CF3	0	O	H	H	n-ButyI	CF2CHF2
527	3-Cl	0	O	H	H	Me	CF2CHF2
528	H	0	O	H	H	c-Propyl	CF(CH3)2	resin
529	3-Cl	0	O	H	H	c-Butyl	CF2CHF2
530	3-OEt	1	O	H	H	CH2-c-Butyl	i-Propyl
531	H	0	O	H	H	Me	i-Propyl	resin
532	3-Me	0	O	H	H	Me	CHFCH3	resin
533	3-F	0	O	H	H	H	CF(CH3)2
534	3-Me,4-F	0	O	H	H	Me	CF2CHF2
535	3-Me	0	O	H	H	Et	CHFCH3	resin
536	3-F	0	O	H	H	Et	i-Propyl
537	H	0	O	H	H	c-Propyl	CF2CHF2
538	3-Cl	0	O	H	H	c-Propyl	CF(CH3)2
539	H	0	O	H	H	c-Butyl	i-Propyl
540	3-Me	0	O	H	H	c-Butyl	CHFCH3
541	3-F	0	O	H	H	c-Butyl	CF(CH3)2
542	3-OMe	0	S	H	H	c-Pentyl	CHFCH3
543	3,5-(OMe)2	0	O	H	H	CH2OMe	CHFCH3
544	3-OMe,5-Cl	0	S	H	H	s-Butyl	CF(CH3)2
545	3-OEt	0	O	H	H	CH2pk OEt	CHFCH3
546	3-F,5-Me	0	S	H	H	t-Butyl	CF3
547	3-CF3	0	O	H	H	Me	CF(CH3)2
548	3-Me,4-F	0	O	H	H	Me	CF(CH3)2
549	3-Me	0	O	H	H	c-Propyl	CF2CHF2
550	3-OMe	0	C(O)O	H	H	i-Propyl	i-Propyl
551	3-Cl,5-Me	0	O	H	H	c-Pentyl	CHFCH3
552	3-Cl	0	O	H	H	Me	CHFCH3
553	3-Me	0	O	H	H	Et	i-Propyl	resin
554	H	0	O	H	H	c-Propyl	i-Propyl	resin
555	3-F	0	O	H	H	c-Propyl	CHFCH3
556	3-Cl	0	O	H	Me	c-Butyl	CHFCH3
557	3,5-(OMe)2	0	O	H	H	CH2-c-Propyl	CF(CH3)2
558	3-OEt	0	O	H	H	CH2-c-Propyl	CF3
559	3-F,5-OMe	0	SO2	H	H	CH2OMe	CF2CHF2
560	3-Cl	0	O	H	H	Me	CF(CH3)2
561	3-F	0	O	H	Et	H	CF2CHF2
562	3-Cl	0	O	H	H	c-Butyl	CF(CH3)2
563	3-OMe,5-Cl	0	O	H	H	CH2F	i-Propyl
564	3-Cl	0	O	H	H	Me	i-Propyl
565	3-F	0	O	H	H	Et	CHFCH3
566	3-Cl	0	O	H	H	c-Butyl	i-Propyl
567	3-OMe,5-Cl	0	O	H	Me	CF3	CF2CHF2
568	H	0	O	H	H	Et	CHFCH3	resin
569	3-F	0	O	H	H	c-Propyl	i-Propyl
570	3,5-Me2	0	O	H	H	CF3	CF2CHF2
571	3-F,5-OMe	0	O	H	H	CH2-c-Propyl	CF3
572	3-F	0	O	H	H	Me	i-Propyl
573	H	0	O	H	H	c-Propyl	CHFCH3	resin
574	3-F	0	O	H	H	H	i-Propyl
575	3-OEt	0	O	H	H	H	CF2CHF2
576	3-Me,4-F	0	O	H	H	H	i-Propyl
577	3-Me	0	O	H	H	c-Propyl	CHFCH3	resin
578	3-OMe	0	O	H	Me	Me	CF3
579	3-Cl,5-Me	0	O	H	H	n-Butyl	CF2CHF2
580	3-F	0	O	H	H	Me	CF2CHF2
581	3-Me,4-F	0	O	H	H	Me	CHFCH3
582	3-Me	0	O	H	H	c-Propyl	CF(CH3)2	resin
583	3-Cl	0	O	H	H	c-Propyl	i-Propyl
584	3-F	0	O	H	H	c-Butyl	CF2CHF2
585	3-OMe	1	0	H	H	n-Butyl	CF2CHF2
586	3-Cl,5-Me	0	O	H	H	i-Propyl	i-Propyl
587	3-F,5-Me	0	O	H	Et	H	CF(CH3)2
588	H	0	O	H	H	Me	CF2CHF2	resin
589	3-Cl	0	O	H	H	Et	CF(CH3)2
590	H	0	O	H	H	c-Butyl	CF2CHF2
591	3,5-F2	0	S	H	H	i-Propyl	i-Propyl
592	3-CF3	0	SO2	H	H	c-Pentyl	CF3
593	3-Me	0	O	H	H	Me	i-Propyl	resin
594	3-Cl	0	O	H	H	Et	CHFCH3
595	3-Me	0	O	H	H	c-Butyl	i-Propyl	resin
596	3,5-F2	0	O	H	H	n-Butyl	CF2CHF2

[0235]

TABLE 4
Compounds of the formula (Id) (=formula I where n = 4
R1, R2, R5, R7, R9 and R10 are each hydrogen and
aryl phenyl which is substituted as shown in the table)
13
								Phys.
No.	Z	m	Y	R	R	R	R	data
597	3-F	0	O	H	H	Me	CHFCH3
598	H	0	O	H	H	Et	CF(CH3)2	oil
599	3-Me	0	O	H	Me	c-Propyl	1-Propyl
600	3-Cl	0	O	H	H	c-Propyl	CF2CHF2
601	3-F	0	O	H	H	c-Butyl	CHFCH3
602	3,5-Me2	0	O	H	H	t-Butyl	1-Propyl
603	3-Cl,5-Me	2	SO2	H	H	Me	CHFCF3
604	3-F,5-Me	0	O	H	H	CH2F	CF(CH3)2
605	H	0	O	H	H	Et	CF2CHF2	oil
606	3-F	0	O	H	H	c-Propyl	CF(CH3)2
607	3,5-Me2	0	O	H	H	CH2F	CHFCH3
608	3-F,5-OMe	0	O	H	H	CH2-c-Butyl	i-Propyl
609	H	0	O	H	H	Me	CF(CH3)2	oil
610	3-Me	0	O	H	H	Me	CF(CH3)2
611	3-Me	0	O	H	H	Et	CF2CHF2
612	3-Cl	0	O	H	H	Et	CF2CHF2
613	H	0	O	H	H	c-Butyl	CF(CH3)2
613	H	0	O	H	H	c-Butyl	CF(CH3)2
614	3-Me	0	O	H	H	c-Butyl	CF(CH3)2
615	3,5-(OMe)2	1	S	H	Et	H	CF(CH3)2
616	3,5-F	0	O	H	H	c-Pentyl	CHFCH3
617	3-CF3	2	S	H	H	1-Propyl	1-Propyl
618	H	0	O	H	H	Et	1-Propyl	oil
619	3-Cl	0	O	H	H	H	CHFCH3
620	3,5-Me2	0	O	H	H	s-Butyl	CHFCF3
621	3-F,5-Me	1	0	H	H	CF3	CHFCH3
622	3-Me	0	O	H	H	Et	CF(CH3)2
623	3-F	0	O	H	H	c-Propyl	CF2CHF2
624	3,5-(OMe)2	1	C(O)O	H	Et	CH2-c-Butyl	CF3
625	3-F,5-OMe	0	0	H	H	CH2OEt	CHFCH3
626	H	0	O	H	H	Me	CHFCH3	oil
627	3-Me	0	O	H	H	Me	CF2CHF2
628	3-Cl	0	O	H	H	Et	i-Propyl
629	3-F	0	O	H	H	Et	CF(CH3)2
630	H	0	O	H	H	c-Butyl	CHFCH3
631	3-Me	0	O	H	H	H	CF2CHF2
632	3,5-F2	1	0	H	Me	Me	CF3
633	3-OMe,5-Cl	0	0	H	H	t-Butyl	i-Propyl
634	3-CF3	0	O	H	H	n-Butyl	CF2CHF2
635	3-Ct	0	O	H	H	Me	CF2CHF2
636	H	0	O	H	H	c-Propyl	CF(CH3)2	oil
637	3-Cl	0	O	H	H	c-Butyl	CF2CHF2
638	3-OEt	1	0	H	H	CH2-c-Butyl	i-Propyl
639	H	0	O	H	H	Me	1-Propyl	oil
640	3-Me	0	O	H	H	Me	CHFCH3
641	3-F	0	O	H	H	H	CF(CH3)2
642	3-Me,4-F	0	O	H	H	Me	CF2CHF2
643	3-Me	1	0	H	H	Et	CHFCH3
644	3-F	0	O	H	H	Et	1-Propyl
645	H	0	O	H	H	c-Propyl	CF2CHF2	oil
646	3-Cl	0	O	H	H	c-Propyl	CF(CH3)2
647	H	0	O	H	H	c-Butyl	i-Propyl
648	3-Me	0	O	H	H	c-Butyl	CHFCH3
649	3-F	1	0	H	H	c-Butyl	CF(CH3)2
650	3-OMe	0	S	H	H	c-Pentyl	CHFCH3
651	3,5-OMe	0	O	H	H	CH2OMe	CHFCH3
652	3-OMe,5-Cl	0	S	H	H	s-Butyl	CF(CH3)2
653	3-OEt	0	O	H	H	CH2OEt	CHFCH3
654	3-F,5-Me	0	S	H	H	t-Butyl	CF3
655	3-CF3	0	O	H	H	Me	CF(CH3)2
656	3-Me,4-F	1	O	H	H	Me	CF(CH3)2
657	3-Me	0	O	H	H	c-Propyl	CF2CHF2
658	3-0Me	0	C(O)O	H	H	i-Propyl	i-Propyl
659	3-Cl,5-Me	0	O	H	H	c-Pentyl	CHFCH3
660	3-Cl	0	O	H	H	Me	CHFCH3
661	3-Me	0	O	H	H	Et	i-Propyl
662	H	1	0	H	H	c-Propyl	i-Propyl
664	3-Cl	0	O	H	Me	c-Butyl	CHFCH3
665	3,5-(OMe)2	0	O	H	H	CH2-c-Propyl	CF(CH3)2
666	3-OEt	0	O	H	H	CH2-c-Propyl	CF3
667	3-F,5-OMe	0	SO2	H	H	CH2OMe	CF2CHF2
668	3-Cl	0	O	H	H	Me	CF(CH3)2
669	3-F	0	O	H	Et	H	CF2CHF2
670	3-Cl	0	O	H	H	c-Butyl	CF(CH3)2
671	3-OMe,5-Cl	0	O	H	H	CH2F	i-Propyl
672	3-Cl	0	O	H	H	Me	i-Propyl
673	3-F	0	O	H	H	Et	CHFCH3
674	3-Cl	0	O	H	H	c-Butyl	i-Propyl
675	3-OMe,5-Cl	0	O	H	Me	CF3	CF2CHF2
676	H	1	0	H	H	Et	CHFCH3
677	3-F	0	O	H	H	c-Propyl	i-Propyl
678	3,5-Me2	0	O	H	H	CF3	CF2CHF2
679	3-F,5-OMe	0	O	H	H	CH2-c-Propyl	CF3
680	3-F	0	O	H	H	Me	i-Propyl
681	H	0	O	H	H	c-Propyl	CHFCH3	oil
682	3-F	0	O	H	H	H	i-Propyl
683	3-OEt	0	O	H	H	H	CF2CHF2
684	3-Me,4-F	0	O	H	H	H	i-Propyl
685	3-Me	0	O	H	H	c-Propyl	CHFCH3
686	3-OMe	0	O	H	Me	Me	CF3
687	3-Cl,5-Me	0	O	H	H	n-Butyl	CF2CHF2
688	3-F	0	O	H	H	Me	CF2CHF2
688	3-F	0	O	H	H	Me	CF2CHF2
689	3-Me,4-F	0	O	H	H	Me	CHFCH3
690	3-Me	0	O	H	H	c-Propyl	CF(CH3)2
691	3-Cl	0	O	H	H	c-Propyl	i-Propyl
692	3-F	0	O	H	H	c-Butyl	CF2CHF2
693	3-OMe	1	O	H	H	n-Butyl	CF2CHF2
694	3-Cl,5-Me	0	O	H	H	i-Propyl	i-Propyl
695	3-F,5-Me	0	O	H	Et	H	CF(CH3)2
696	H	0	O	H	H	Me	CF2CHF2	oil
697	3-Cl	0	O	H	H	Et	CF(CH3)2
698	H	0	O	H	H	c-Butyl	CF2CHF2	oil
699	3,5-F	1	S	H	H	i-Propyl	i-Propyl
700	3-CF3	0	SO2	H	H	c-Pentyl	CF3
701	3-Me	0	O	H	H	Me	i-Propyl
702	3-Cl	0	O	H	H	Et	CHFCH3
703	3-Me	0	O	H	H	c-Butyl	i-Propyl
704	3,5-F2	0	O	H	H	n-Butyl	CF2CHF2

[0236]

TABLE 5
Compounds of the formula (Ie) (=formula I where n = 5, R1, R2,
R5, R7, R9 and R10 are each hydrogen and
aryl = phenyl which is substituted as shown in the table)
14
								Phys.
No.	Z	m	Y	R3	R4	R6	R8	data
705	3-F	0	O	H	H	Me	CHFCH3
706	H	0	O	H	H	Et	CF(CH3)2
707	3-Me	0	O	H	Me	c-Propyl	i-Propyl
708	3-Cl	0	O	H	H	c-Propyl	CF2CHF2
709	3-F	0	O	H	H	c-Butyl	CHFCH3
710	3,5-Me2	0	O	H	H	t-Butyl	i-Propyl
711	3-Cl,5-Me	2	SO2	H	H	Me	CHFCF3
712	3-F,5-Me	0	O	H	H	CH2F	CF(CH3)2
713	H	0	O	H	H	Et	CF2CHF2
714	3-F	0	O	H	H	c-Propyl	CF(CH3)2
715	3,5-Me2	0	O	H	H	CH2F	CHFCH3
716	3-F,5-OMe	0	O	H	H	CH2-cButyl	i-Propyl
717	H	0	O	H	H	Me	CF(CH3)2
718	3-Me	0	O	H	H	Me	CF(CH3)2
719	3-Me	0	O	H	H	Et	CF2CHF2
720	3-Cl	0	O	H	H	Et	CF2CHF2
721	H	0	O	H	H	c-Butyl	CF(CH3)2
722	3-Me	0	O	H	H	c-Butyl	CF(CH3)2
723	3,5-(OMe)2	1	S	H	Et	H	CF(CH3)2
724	3,5-F2	0	O	H	H	c-Pentyl	CHFCH3
725	3-CF3	2	S	H	H	i-Propyl	i-Propyl
726	H	0	O	H	H	Et	i-Propyl
727	3-Cl	0	O	H	H	H	CHFCH3
728	3,5-Me2	0	O	H	H	s-Butyl	CHFCF3
729	3-F,5-Me	1	0	H	H	CF3	CHFCH3
730	3-Me	0	O	H	H	Et	CF(CH3)2
731	3-F	0	O	H	H	c-Propyl	CF2CHF2
732	3,5-(OMe)2	1	C(O)O	H	Et	CH2-c-Butyl	CF3
733	3-F,5-OMe	0	O	H	H	CH2OEt	CHFCH3
734	H	0	O	H	H	Me	CHFCH3
735	3-Me	0	O	H	H	Me	CF2CHF2
736	3-Cl	0	O	H	H	Et	i-Propyl
737	3-F	0	O	H	H	Et	CF(CH3)2
738	H	0	O	H	H	c-Butyl	CHFCH3
739	3-Me	0	O	H	H	H	CF2CHF2
740	3,5-F2	1	0	H	Me	Me	CF3
741	3-OMe,	0	O	H	H	1-Butyl	i-Propyl
	5-Cl
742	3-CF3	0	O	H	H	n-Butyl	CF2CHF2
743	3-Cl	0	O	H	H	Me	CF2CHF2
744	H	0	O	H	H	c-Propyl	CF(CH3)2
745	3-Cl	0	O	H	H	c-Butyl	CF2CHF2
746	3-OEt	1	0	H	H	CH2-c-Butyl	i-Propyl
747	H	0	O	H	H	Me	i-Propyl
748	3-Me	0	O	H	H	Me	CHFCH3
749	3-F	0	O	H	H	H	CF(CH3)2
750	3-Me,4-F	0	O	H	H	Me	CF2CHF2
751	3-Me	1	0	H	H	Et	CHFCH3
752	3-F	0	O	H	H	Et	i-Propyl
753	H	0	O	H	H	c-Propyl	CF2CHF2
754	3-Cl	0	O	H	H	c-Propyl	CF(CH3)2
755	H	0	O	H	H	c-Butyl	i-Propyl
756	3-Me	0	O	H	H	c-Butyl	CHFCH3
757	3-F	1	O	H	H	c-Butyl	CF(CH3)2
758	3-OMe	0	S	H	H	c-Pentyl	CHFCH3
759	3,5-(OMe)2	0	O	H	H	CH2OMe	CHFCH3
760	3-OMe, 5-Cl	0	S	H	H	s-Butyl	CF(CH3)2
761	3-OEt	0	O	H	H	CH2OEt	CHFCH3
762	3-F,5-Me	0	S	H	H	t-Butyl	CF3
763	3-CF3	0	O	H	H	Me	CF(CH3)2
764	3-Me,4-F	1	0	H	H	Me	CF(CH3)2
765	3-Me	0	O	H	H	c-Propyl	CF2CHF2
766	3-OMe	0	C(O)O	H	H	i-Propyl	i-Propyl
767	3-Cl,5-Me	0	O	H	H	c-Pentyl	CHFCH3
768	3-Cl	0	O	H	H	Me	CHFCH3
769	3-Me	0	O	H	H	Et	i-Propyl
770	H	1	O	H	H	c-Propyl	i-Propyl
771	3-F	0	O	H	H	c-Propyl	CHFCH3
772	3-Cl	0	O	H	Me	c-Butyl	CHFCH3
773	3,5-(OMe)2	0	O	H	H	CH2-c-Propyl	CF(CH3)2
774	3-OEt	0	O	H	H	CH2-c-Propyl	CF3
775	3-F,5-OMe	0	SO2	H	H	CH2OMe	CF2CHF2
776	3-Cl	0	O	H	H	Me	CF(CH3)2
777	3-F	0	O	H	Et	H	CF2CHF2
778	3-Cl	0	O	H	H	c-Butyl	CF(CH3)2
779	3-OMe,5-Cl	O	O	H	H	CH2F	i-Propyl
780	3-Cl	0	O	H	H	Me	i-Propyl
781	3-F	0	O	H	H	Et	CHFCH3
782	3-Cl	0	O	H	H	c-Butyl	i-Propyl
783	3-OMe,5-Cl	0	O	H	Me	CF3	CF2CHF2
784	H	1	O	H	H	Et	CHFCH3
785	3-F	0	O	H	H	c-Propyl	i-Propyl
786	3,5-Me2	0	O	H	H	CF3	CF2CHF2
787	3-F,5-OMe	0	O	H	H	CH2-c-Propyl	CF3
788	3-F	0	O	H	H	Me	i-Propyl
789	H	0	O	H	H	c-Propyl	CHFCH3
790	3-F	0	O	H	H	H	i-Propyl
791	3-OEt	0	O	H	H	H	CF2CHF2
792	3-Me,4-F	0	O	H	H	H	i-Propyl
793	3-Me	0	O	H	H	c-Propyl	CHFCH3
794	3-OMe	0	O	H	Me	Me	CF3
795	3-Cl,5-Me	0	O	H	H	n-Butyl	CF2CHF2
796	3-F	0	O	H	H	Me	CF2CHF2
797	3-Me,4-F	0	O	H	H	Me	CHFCH3
798	3-Me	0	O	H	H	c-Propyl	CF(CH3)2
799	3-Cl	0	O	H	H	c-Propyl	i-Propyl
800	3-F	0	O	H	H	c-Butyl	CF2CHF2
801	3-OMe	1	0	H	H	n-Butyl	CF2CHF2
802	3-Cl,5-Me	0	O	H	H	i-Propyl	i-Propyl
803	3-F,5-Me	0	O	H	Et	H	CF(CH3)2
804	H	0	O	H	H	Me	CF2CHF2
805	3-Cl	0	O	H	H	Et	CF(CH3)2
806	H	0	O	H	H	c-Butyl	CF2CHF2
807	3,5-F2	1	S	H	H	i-Propyl	i-Propyl
808	3-CF3	0	SO2	H	H	c-Pentyl	CF3
809	3-Me	0	O	H	H	Me	i-Propyl
810	3-Cl	0	O	H	H	Et	CHFCH,
811	3-Me	0	O	H	H	c-Butyl	i-Propyl
812	3,5-F2	0	O	H	H	n-Butyl	CF2CHF2

[0237]

TABLE 6
Compounds of the formula (If) (=compounds of the formula (I)
in which m = 0, Y = O, (CR3R4)n-CR5R6 =
cyclohexane-1,3-diyl, R7 = H, R9 = H and aryl =
phenyl which is substituted as shown in the table)
15
	No.	Z	R8	Phys. data
	813	3,4-F2	i-Propyl
	814	3,4-F2	CF(CH3)2
	815	3,4-F2	CHFCH3
	816	3,4-F2	CF2CHF2
	817	3,5-Me2	CF(CH3)2
	818	3,5-Me2	CHFCH3
	819	3,5-Me2	CF(CH3)2
	820	3,5-Me2	CHFCH3
	821	3-Cl	CF(CH3)2
	822	3-Cl	CHFCH3
	823	3-Cl,5-F	CF(CH3)2
	824	3-Cl,5-F	CHFCH3
	825	3-F	CF(CH3)2
	826	3-F	CHFCH3
	827	3-Me	CCl(CH3)3
	828	3-Me	Et
	829	3-Me	CF2CF3
	830	3-Me	CF(CH3)2
	831	3-Me	CHFCH3
	832	3-Me,4-F	CF(CH3)2
	833	3-Me,4-F	CHFCH3
	834	4-F	1-Propyl
	835	4-F	CF(CH3)2
	836	4-F	CHFCH3
	837	4-F	CF2CHF2
	838	H	CCl(CH3)2
	839	H	Me
	840	H	CF(CH3)2
	841	H	CHFCH3

[0238]

TABLE 7
Compounds of the formula (Ig) (=compounds of the formula (I),
in which m = 0, Y = O, (CR3R4)n-CR5R6 =
—CH2-1,2-cycloC6H10—, R7 = R9 =R10 =
H and aryl = phenyl which is substituted as shown in the table)
16
	No.	Z	R8	Phys. data
	842	3,4-F2	i-Propyl
	843	3,4-F2	CF(CH3)2
	844	3,4-F2	CHFCH3
	845	3,4-F2	CF2CHF2
	846	3,5-Me2	CF(CH3)2
	847	3,5-Me2	CHFCH3
	848	3,5-Me2	CF(CH3)2
	849	3,5-Me2	CHFCH3
	850	3-Cl	CF(CH3)2
	851	3-Cl	CHFCH3
	852	3-Cl,5-F	CF(CH3)2
	853	3-Cl,5-F	CHFCH3
	854	3-F	CF(CH3)2
	855	3-F	CHFCH3
	856	3-Me	CCl(CH3)3
	857	3-Me	Et
	858	3-Me	CF2CF3
	859	3-Me	CF(CH3)2
	860	3-Me	CHFCH3
	861	3-Me,4-F	CF(CH3)2
	862	3-Me,4-F	CHFCH3
	863	4-F	1-Propyl
	864	4-F	CF(CH3)2
	865	4-F	CHFCH3
	868	4-F	CF2CHF2
	867	H	CCl(CH3)2
	868	H	Me
	869	H	CF(CH3)2	resin
	870	H	CHFCH3	resin

[0239]

TABLE 8
Compounds of the formula (Ih) (=formula (I), in which m = 0, Y = O,
(CR3R4)n—CR5R6 = —CH21,2-cyclopentyl-,
R7, R9, R10 are each H and aryl = phenyl
which is substituted as shown in the table)
17
	No.	Z	R8	Phys. data
	871	3,4-F2	i-Propyl
	872	3,4-F2	CF(CH3)2
	873	3,4-F2	CHFCH3
	874	3,4-F2	CF2CHF2
	875	3,5-Me2	CF(CH3)2
	876	3,5-Me2	CHFCH3
	877	3,5-Me2	CF(CH3)2
	878	3,5-Me2	CHFCH3
	879	3-Cl	CF(CH3)2
	880	3-Cl	CHFCH3
	881	3-Cl,5-F	CF(CH3)2
	882	3-Cl,5-F	CHFCH3
	883	3-F	CF(CH3)2
	884	3-F	CHFCH3
	885	3-Me	CCl(CH3)3
	886	3-Me	Et
	887	3-Me	CF2CF3
	888	3-Me	CF(CH3)2
	889	3-Me	CHFCH3
	890	3-Me,4-F	CF(CH3)2
	891	3-Me,4-F	CHFCH3
	892	4-F	i-Propyl
	893	4-F	CF(CH3)2
	894	4-F	CHFCH3
	895	4-F	CF2CHF2
	896	H	CCl(CH3)2
	897	H	Me
	898	H	CF(CH3)2
	899	H	CHFCH3

[0240]

TABLE 9
Compounds of the formula (Ik) (=formula (I), in which m = 1,
n = 1, R1 and R2 are each H, (CR3R4) =
carbonyl; R5, R7, R9, R10 are each H and
aryl = phenyl which is substituted as shown in the table)
18
No.	Z	Y	R6	R8	Phys. data
900	3-F	O	Me	CHFCH3
901	H	O	Et	CF(CH3)2
902	3-Me	O	c-Propyl	i-Propyl
903	3-Cl	O	CH2CH2SCH3	CF2CHF2
904	3-F	N	c-Butyl	CHFCH3
905	3,5-Me2	N	t-Butyl	i-Propyl
906	3-Cl,5-Me	N	Me	CHFCF3
907	3-F,5-Me	O	Benzyl	CF(CH3)2
908	H	N	Et	CF2CHF2
909	3-F	O	c-Propyl	CF(CH3)2
910	3,5-Me2	N	CH2F	CHFCH3
911	3,5-Me2	N	s-Butyl	CHFCH3
912	3-F,5-OMe	O	CH2-c-Butyl	1-Propyl
913	H	N	Me	CF(CH3)2
914	3-Me	O	CH2CH2SCH3	CF(CH3)2
915	3-Me	N	Et	CF2CHF2
916	3-Cl	O	Et	CF2CHF2
917	H	O	c-Butyl	CF(CH3)2
918	3-Me	O	c-Butyl	CF(CH3)2
919	H	N	Et	Me
920	3,5-F2	O	c-Pentyl	CHFCH3
921	3-CF3	O	i-Propyl	i-Propyl
922	H	N	Et	i-Propyl
923	3-Cl	O	Benzyl	CHFCH3
924	H	O	CH2CH2SCH3	Me
925	3-F,5-Me	O	CF3	CHFCH3
926	3-Me	N	Me	CF(CH3)2	m.p.
					98° C.
927	3-F	N	c-Propyl	CF2CHF2
928	3,5-(OMe)2	N	CH2-c-Butyl	CF3
929	3-F,5-OMe	N	CH2OEt	CHFCH3
930	H	N	H	CHFCH3	m.p.
					123° C.
931	3-Me	N	Me	CF2CHF2
932	3-Cl	N	Et	i-Propyl
933	3-F	N	Et	CF(CH3)2
934	H	N	Et	Et
935	3-Me	N	Benzyl	CF2CHF2
938	3,5-F2	N	Me	CF3
937	3-OMe,5-Cl	O	t-Butyl	i-Propyl
938	3-CF3	O	i-Butyl	CF2CHF2
939	3-Cl	O	Me	CF2CHF2
940	H	O	c-Propyl	CF(CH3)2
941	3-Cl	O	c-Butyl	CF2CHF2
942	3-OEt	N	CH2-c-Butyl	i-Propyl
943	H	N	Me	i-Propyl
944	3-Me	N	Me	CHFCH3
945	3-F	N	H	CF(CH3)2
946	3-Me,4-F	N	Me	CF2CHF2
947	3-Me	N	Et	CHFCH3
948	3-F	N	Et	i-Propyl
949	H	N	c-Propyl	CF2CHF2
950	3-Cl	N	c-Propyl	CF(CH3)2
951	H	N	s-Butyl	Me
952	3-Me	N	c-Butyl	CHFCH3
953	3-F	N	c-Butyl	CF(CH3)2
954	3-OMe	N	c-Pentyl	CHFCH3
955	3,5-(OMe)2	N	CH2OMe	CHFCH3
956	3-OMe,5-Cl	N	CH2CH2SCH3	CF(CH3)2
957	3-OEt	N	CH2OEt	CHFCH3
958	3-F,5-Me	N	1-Butyl	CF3
959	3-CF3	N	Me	CF(CH3)2
960	3-Me,4-F	N	Me	CF(CH3)2
961	3-Me	N	c-Propyl	CF2CHF2
962	3-OMe	N	Benzyl	i-Propyl
963	3-Cl,5-Me	O	c-Pentyl	CHFCH3
964	3-Cl	O	Me	CHFCH3
965	3-Me	O	Et	i-Propyl
966	H	O	c-Propyl	i-Propyl
967	3-F	N	c-Propyl	CHFCH3
968	3-Cl	N	c-Butyl	CHFCH3
969	3,5-(OMe)2	N	CH2-cPropyl	CF(CH3)2
970	3-OEt	N	i-ButyI	CF3
971	3-F,5-OMe	N	CH2OMe	CF2CHF2
972	3-Cl	N	Me	CF(CH3)2
973	3-F	N	H	CF2CHF2
974	3-Cl	N	c-Butyl	CF(CH3)2
975	3-OMe,5-Cl	N	CH2F	i-Propyl
976	3-Cl	N	Me	i-Propyl
977	3-F	N	CH2CH2SCH3	CHFCH3
978	3-Ct	N	c-Butyl	i-Propyl
979	3-OMe,5-Cl	N	CF3	CF2CHF2
980	H	N	Et	CHFCH3
981	3-F	N	c-Propyl	i-Propyl
982	3,5-Me2	N	CF3	CF2CHF2
983	3-F,5-OMe	O	CH2-c-Propyl	CF3
984	3-F	O	Me	i-Propyl
985	H	O	c-Propyl	CHFCH3
986	3-F	O	H	i-Propyl
987	H	N	H	i-Propyl	m.p.
					143° C.
988	3-Me,4-F	O	H	i-Propyl
989	3-Me	N	c-Propyl	CHFCH3
990	3-OMe	N	Me	CF3
991	3-Cl,5-Me	N	n-Butyl	CF2CHF2
992	3-F	N	Me	CF2CHF2
993	3-Me,4-F	N	Me	CHFCH3
994	3-Me	N	c-Propyl	CF(CH3)2
995	3-Cl	N	c-Propyl	i-Propyl
996	3-F	N	c-Butyl	CF2CHF2
997	3-OMe	N	n-Butyl	CF2CHF2
998	3-Cl,5-Me	N	Benzyl	i-Propyl
999	3-F,5-Me	N	H	CF(CH3)2
1000	H	N	Me	CF2CHF2
1001	3-Cl	N	Et	CF(CH3)2
1002	H	N	c-Butyl	CF2CHF2
1003	3,5-F	N	i-Propyl	i-Propyl
1004	3-CF3	N	c-Pentyl	CF3
1005	3-Me	N	Me	i-Propyl	m.p.
					112° C.
1006	3-Cl	N	Et	CHFCH3
1007	3-Me	N	c-Butyl	i-Propyl
1008	3,5-F2	N	n-Butyl	CF2CHF2

[0241]

Table 10
Compounds of the formula (Im) (=formula (I), in which m = 0,
n = 1, Y = —NH—CO—NH—, R3 and R4 are each
H; R5, R7, R9, R10 are each H and aryl =
phenyl which is substituted as shown in the table)
19
No.	Z	R6	R8	Phys. data
1009	3-F	Me	CHFCH3
1010	H	Et	CF(CH3)2
1011	3-Me	c-Propyl	i-Propyl
1012	3-Cl	Pentyl	CF2CHF2
1013	3-F	c-Butyl	CHFCH3
1014	3,5-Me2	t-Butyl	1-Propyl
1015	3-Cl,5-Me	Me	CHFCF3
1016	3-F,5-Me	CH2OEt	CF(CH3)2
1017	H	Et	CF2CHF2
1018	3-F	c-Propyl	CF(CH3)2
1019	3,5-Me2	CH2F	CHFCH3
1020	3,5-Me2	s-Butyl	CHFCH3
1021	3-F,5-OMe	CH2-c-Butyl	i-Propyl
1022	H	Me	CF(CH3)2
1023	3-Me	CH2OMe	CF(CH3)2
1024	3-Me	Et	CF2CHF2
1025	3-Cl	Et	CF2CHF2
1026	H	c-Butyl	CF(CH3)2
1027	3-Me	c-Butyl	CF(CH3)2
1028	H	Et	Me
1029	3,5-F2	c-Pentyl	CHFCH3
1030	3-CF3	i-Propyl	i-Propyl
1031	H	Et	i-Propyl
1032	3-Cl	CH2OEt	CHFCH3
1033	H	CH2OMe	Me
1034	3-F,5-Me	CF3	CHFCH3
1035	3-Me	Me	CF(CH3)2
1036	3-F	c-Propyl	CF2CHF2
1037	3,5-(OMe)2	CH2-c-Butyl	CF3
1038	3-F,5-OMe	CH2OEt	CHFCH3
1039	H	H	CHFCH3
1040	3-Me	Me	CF2CHF2
1041	3-Cl	Et	i-Propyl
1042	3-F	Et	CF(CH3)2
1043	H	Et	Et
1044	3-Me	Pentyl	CF2CHF2
1045	3,5-F2	Me	CF3
1046	3-OMe,5-Cl	t-Butyl	i-Propyl
1047	3-CF3	i-Butyl	CF2CHF2
1048	3-Cl	Me	CF2CHF2
1049	H	c-Propyl	CF(CH3)2
1050	3-Cl	c-Butyl	CF2CHF2
1051	3-OEt	CH2-c-Butyl	i-Propyl
1052	H	Me	i-Propyl
1053	3-Me	Me	CHFCH3
1054	3-F	H	CF(CH3)2
1055	3-Me,4-F	Me	CF2CHF2
1056	3-Me	Et	CHFCH3
1057	3-F	Et	i-Propyl
1058	H	c-Propyl	CF2CHF2
1059	3-Cl	c-Propyl	CF(CH3)2
1060	H	s-Butyl	Me
1061	3-Me	c-Butyl	CHFCH3
1062	3-F	c-Butyl	CF(CH3)2
1063	3-OMe	c-Pentyl	CHFCH3
1064	3,5-(OMe)2	CH2OMe	CHFCH3
1065	3-OMe,5-Cl	H	CF(CH3)2
1066	3-QEt	CH2OEt	CHFCH3
1067	3-F,5-Me	1-Butyl	CF3
1068	3-CF3	Me	CF(CH3)2
1069	3-Me,4-F	Me	CF(CH3)2
1070	3-Me	c-Propyl	CF2CHF2
1071	3-OMe	Pentyl	i-Propyl
1072	3-Cl,5-Me	c-Pentyl	CHFCH3
1073	3-Cl	Me	CHFCH3
1074	3-Me	Et	i-Propyl
1075	H	c-Propyl	i-P ropyl
1076	3-F	c-Propyl	CHFCH3
1078	3,5-(OMe)2	CH2-cPropyl	CF(CH3)2
1079	3-CEt	1-Butyl	CF3
1080	3-F,5-OMe	CH2OMe	CF2CHF2
1081	3-Cl	Me	CF(CH3)2
1082	3-F	H	CF2CHF2
1083	3-Cl	c-Butyl	CF(CH3)2
1084	3-OMe,5-Cl	CH2F	i-Propyl
1085	3-Cl	Me	i-Propyl
1086	3-F	CH2OEt	CHFCH3
1087	3-Cl	c-Butyl	i-Propyl
1088	3-OMe,5-Cl	CF3	CF2C HF2
1089	H	Et	CHFCH3
1090	3-F	c-Propyl	i-Propyl
1091	3,5-Me2	CF3	CF2CHF2
1092	3-F,5-OMe	CH2-c-Propyl	CF3
1093	3-F	Me	i-Propyl
1094	H	c-Propyl	CHFCH3
1095	3-F	H	i-Propyl
1096	H	H	i-Propyl
1097	3-Me,4-F	H	i-Propyl
1098	3-Me	c-Propyl	CHFCH3
1099	3-OMe	Me	CF3
1100	3-Cl,5-Me	n-Butyl	CF2CHF2
1101	3-F	Me	CF2CHF2
1102	3-Me,4-F	Me	CHFCH3
1103	3-Me	c-Propyl	CF(CH3)2
1104	3-Cl	c-Propyl	i-Propyl
1105	3-F	c-Butyl	CF2CHF2
1106	3-OMe	n-Butyl	CF2CHF2
1107	3-Cl,5-Me	Hexyl	i-Propyl
1108	3-F,5-Me	H	CF(CH3)2
1109	H	Me	CF2CHF2
1110	3-Cl	Et	CF(CH3)2
1111	H	c-Butyl	CF2CHF2
1112	3,5-F2	i-Propyl	i-Propyl
1113	3-CF3	c-Pentyl	CF3
1114	3-Me	Me	i-Propyl
1115	3-Cl	Et	CHFCH3
1116	3-Me	c-Butyl	i-Propyl
1117	3,5-F2	n-Butyl	CF2CHF2

[0242]

TABLE 11
Compounds of the formula (In) (=formula (I), in which m = 0, n = 1,
Y = —NH—CO—O—, R3 and R4 are each H; R5, R7,
R9, R10 are each H and aryl = phenyl which
is substituted as shown in the table)
20
No.	Z	R6	R8	Phys. data
1118	3-Me,4-F	H	i-Propyl
1119	3-Me	c-Propyl	CHFCH3
1120	3-OMe	Me	CF3
1121	3-Cl	Pentyl	CF2CHF2
1122	3-F	c-Butyl	CHFCH3
1123	3,5-Me2	1-Butyl	1-Propyl
1124	3-Cl,5-Me	Me	CHFCF3
1125	3-F,5-Me	CH2OEt	CF(CH3)2
1126	H	Et	CF2CHF2
1127	3-F	c-Propyl	CF(CH3)2
1128	3-Cl	Et	CF(CH3)2
1129	H	c-Butyl	CF2CHF2
1130	3,5-F2	1-Propyl	1-Propyl
1131	3-CF3	c-Pentyl	CF3
1132	3-Me	Me	i-Propyl
1133	3-F	Me	CHFCH3
1134	H	Et	CF(CH3)2
1135	3-Me	c-Propyl	i-Propyl
1136	3-Me	Et	CF2CHF2
1137	3-Cl	Et	CF2CHF2
1138	H	c-Butyl	CF(CH3)2
1139	3-Me	c-Butyl	CF(CH3)2
1140	H	Et	Me
1141	3,5-F2	c-Pentyl	CHFCH3
1142	3-CF3	i-Propyl	1-Propyl
1143	H	Et	1-Propyl
1144	3-Cl	CH2OEt	CHFCH3
1145	H	CH2OMe	Me
1146	3-F,5-Me	CF3	CHFCH3
1147	3,5-Me2	CH2F	CHFCH3
1148	3,5-Me2	s-Butyl	CHFCH3
1149	3-F,5-OMe	CH2-c-Butyl	i-Propyl
1150	H	Me	CF(CH3)2
1151	3-Me	CH2OMe	CF(CH3)2
1152	3-Me	Me	CF(CH3)2
1153	3-F	c-Propyl	CF2CHF2
1154	3,5-(OMe)2	CH2-c-Butyl	CF3
1155	3-F,5-OMe	CH2OEt	CHFCH3
1156	H	H	CHFCH3
1157	3-Me	Me	CF2CHF2
1158	3-Cl	Et	1-Propyl
1159	3-F	Et	CF(CH3)2
1160	H	Et	Et
1161	3-Me	Pentyl	CF2CHF2
1162	3,5-F2	Me	CF3
1163	3-OMe,5-Cl	t-Butyl	1-Propyl
1164	3-CF3	i-Butyl	CF2CHF2
1165	3-Cl	Me	CF2CHF2
1166	H	c-Propyl	CF(CH3)2
1167	3-Cl	c-Butyl	CF2CHF2
1168	3-OEt	CH2-c-Butyl	i-Propyl
1169	H	Me	i-Propyl
1170	3-Me	Me	CHFCH3
1171	3-F	H	CF(CH3)2
1172	3-Me,4-F	Me	CF2CHF2
1173	3-Me	Et	CHFCH3
1174	3-F	Et	i-Propyl
1175	H	c-Propyl	CF2CHF2
1176	3-Cl	c-Propyl	CF(CH3)2
1177	H	s-Butyl	Me
1178	3-Me	c-Butyl	CHFCH3
1179	3-F	c-Butyl	CF(CH3)2
1180	3-OMe	c-Pentyl	CHFCH3
1181	3,5-(OMe)2	CH2OMe	CHFCH3
1182	3-OMe,5-Cl	H	CF(CH3)2
1183	3-OEt	CH2OEt	CHFCH3
1184	3-F,5-Me	t-Butyl	CF3
1185	3-CF3	Me	CF(CH3)2
1186	3-Me,4-F	Me	CF(CH3)2
1187	3-Me	c-Propyl	CF2CHF2
1188	3-OMe	Pentyl	i-Propyl
1189	3-Cl,5-Me	c-Pentyl	CHFCH3
1190	3-Cl	Me	CHFCH3
1191	3-Me	Et	i-Propyl
1192	H	c-Propyl	i-Propyl
1193	3-F	c-Propyl	CHFCH3
1194	3-Cl	c-Butyl	CHFCH3
1195	3,5-(OMe)2	CH2-cPropyl	CF(CH3)2
1196	3-OEt	1-Butyl	CF3
1197	3-F,5-OMe	CH2OMe	CF2CHF2
1198	3-Cl	Me	CF(CH3)2
1199	3-F	H	CF2CHF2
1200	3-Cl	c-Butyl	CF(CH3)2
1201	3-OMe,5-Cl	CH2F	i-Propyl
1202	3-Cl	Me	i-Propyl
1203	3-F	CH2OEt	CHFCH3
1204	3-Cl	c-Butyl	i-Propyl
1205	3-OMe,5-Cl	CF3	CF2CHF2
1206	H	Et	CHFCH3
1207	3-F	c-Propyl	i-Propyl
1208	3,5-Me2	CF3	CF2CHF2
1209	3-F,5-OMe	CH2-c-Propyl	CF3
1210	3-F	Me	i-Propyl
1211	H	c-Propyl	CHFCH3
1212	3-F	H	i-Propyl
1213	H	H	i-Propyl
1214	3-Cl	Et	CHFCH3
1215	3-Me	c-Butyl	i-Propyl
1216	3,5-F2	n-Butyl	CF2CHF2
1217	3-Cl,5-Me	n-Butyl	CF2CHF2
1218	3-F	Me	CF2CHF2
1219	3-Me,4-F	Me	CHFCH3
1220	3-Me	c-Propyl	CF(CH3)2
1221	3-Cl	c-Propyl	i-Propyl
1222	3-F	c-Butyl	CF2CHF2
1223	3-OMe	n-Butyl	CF2CHF2
1224	3-Cl,5-Me	Hexyl	i-Propyl
1225	3-F,5-Me	H	CF(CH3)2
1226	H	Me	CF2CHF2

[0243]

TABLE 12
Compounds of the formula (Io) (=formula (I), in which m = 1, n = 1,
Y = —O—N═, R3 = linkage point for double bond,
R4 = H; R5; R7, R9, R10 are each H and
aryl = phenyl which is substituted as shown in the table)
21
No.	Z	R9	R8	Phys. data
1227	3-F,5-OMe	CH2OMe	CF2CHF2
1228	3-Cl	Me	CF(CH3)2
1229	3-F	H	CF2CHF2
1230	3-Cl	Pentyl	CF2CHF2
1231	3-F	c-Butyl	CHFCH3
1232	3,5-Me2	1-Butyl	i-propyl
1233	3-Cl,5-Me	Me	CHFCF3
1234	3,5-Me2	H	CHFCH3	resin
1235	3,5-Me2	H	Et	resin
1236	3,5-Me2	H	CF(CH3)2	resin
1237	H	Et	CF2CHF2
1238	3-F	c-Propyl	CF(CH3)2
1239	3-Cl	Et	CF(CH3)2
1240	H	c-Butyl	CF2CHF2
1241	3,5-F2	i-Propyl	i-propyl
1242	3-CF3	c-Pentyl	CF3
1243	3-Me	Me	i-propyl
1244	3-F	Me	CHFCH3
1245	H	Et	CF(CH3)2
1246	3-Me	c-Propyl	i-propyl
1247	3-Me	Et	CF2CHF2
1248	3-Cl	Et	CF2CHF2
1249	H	c-Butyl	CF(CH3)2
1250	3-Me	c-Butyl	CF(CH3)2
1251	3,5-Me2	H	CH(CH3)2	resin
1252	H	H	CF(CH3)2	resin
1253	H	H	CH(CH3)2	resin
1254	H	Et	Me
1255	3-Me,4-F	H	i-Propyl
1256	3-Me	c-Propyl	CHFCH3
1257	3-OMe	Me	CF3
1258	3,5-F2	c-Pentyl	CHFCH3
1259	3-CF3	i-Propyl	i-Propyl
1260	H	Et	i-propyl
1261	3-Cl	CH2OEt	CHFCH3
1262	H	CH2OMe	Me
1263	3-F,5-Me	CF3	CHFCH3
1264	3,5-Me2	CH2F	CHFCH3
1265	3,5-Me2	s-Butyl	CHFCH3
1266	3-F,5-OMe	CH2-c-Butyl	i-Propyl
1267	H	Me	CF(CH3)2
1268	3-Me	CH2OMe	CF(CH3)2
1269	3-Me	Me	CF(CH3)2
1270	3-F	c-Propyl	CF2CHF2
1271	3,5-(OMe)2	CH2-c-Butyl	CF3
1272	3-F,5-OMe	CH2OEt	CHFCH3
1273	H	H	Me
1274	3-Me	Me	CF2CHF2
1275	3-Cl	Et	i-Propyl
1276	3-F	Et	CF(CH3)2
1277	H	Et	Et
1278	3-Me	Pentyl	CF2CHF2
1279	3,5-F2	Me	CF3
1280	3-OMe,5-Cl	i-Butyl	i-propyl
1281	3-CF3	i-Butyl	CF2CHF2
1282	3-Cl	Me	CF2CHF2
1283	H	c-Propyl	CF(CH3)2
1284	3-Cl	c-Butyi	CF2CHF2
1285	3-OEt	CHrC-BLityl	i-Propyl
1286	H	Me	i-propyl
1287	3-Me	Me	CHFCH3
1288	3-F	H	CF(CH3)2
1289	3-Me,4-F	Me	CF2CHF2
1290	3-Me	Et	CHFCH3
1291	3-F	Et	i-propyl
1292	H	c-Propyl	CF2CHF2
1293	3-Cl	c-Propyl	CF(CH3)2
1294	H	s-Butyl	Me
1295	3-Me	c-Butyl	CHFCH3
1296	3-F	c-Butyl	CF(CH3)2
1297	3-OMe	c-Pentyi	CHFCH3
1298	3,5-OMe	CH2OMe	CHFCH3
1299	3-OMe,5-Cl H	CF(CH3)2
1300	3-OEt	CH2OEt	CHFCH3
1301	3-F,5-Me	i-Butyl	CF3
1302	3-CF3	Me	CF(CH3)2
1303	3-Me,4-F	Me	CF(CH3)2
1304	3-Me	c-Propyl	CF2CHF2
1305	3-OMe	Pentyl	i-propyl
1306	3-Cl,5-Me	c-Pentyl	CHFCH3
1307	H	H	CHFCH3	resin
1308	3-Cl	Me	CHFCH3
1309	3-Me	Et	i-Propyl
1310	H	c-Propyl	i-propyl
1311	3-F	c-Propyl	CHFCH3
1312	3-Cl	c-Butyl	CHFCH3
1313	3,5-(OMe)2	CH2-cPropyl	CF(CH3)2
1314	3-OEt	i-Butyl	CF3
1315	3-Cl,5-Me	Hexyl	i-propyl
1316	3-F,5-Me	H	CF(CH3)2
1317	H	Me	CF2CHF2
1318	3-Cl	c-Butyl	CF(CH3)2
1319	3-OMe,5-Cl	CH2F	i-Propyl
1320	3-Cl	Me	i-Propyl
1321	3-F	CH2OEt	CHFCH3
1322	3-Cl	c-Butyl	i-Propyl
1323	3-OMe,5-Cl	CF3	CF2CHF2
1324	H	Et	CHFCH3
1325	3-F	c-Propyl	i-Propyl
1326	3,5-Me2	CF3	CF2CHF2
1327	3-F,5-OMe	CH2-c-Propyl	CF3
1328	3-F	Me	i-Propyl
1329	H	c-Propyl	CHFCH3
1330	3-F	H	i-Propyl
1331	H	H	Et
1332	3-Cl	Et	CHFCH3
1333	3-Me	c-Butyl	i-Propyl
1334	3,5-F2	n-Butyl	CF2CHF2
1335	3-Cl,5-Me	n-Butyl	CF2CHF2
1336	3-F	Me	CF2CHF2
1337	3-Me,4-F	Me	CHFCH3
1338	3-Me	c-Propyl	CF(CH3)2
1339	3-Cl	c-Propyl	i-propyl
1340	3-F	c-Butyl	CF2CHF2
1341	3-OMe	n-Butyl	CF2CHF2

[0244]

TABLE 13
Compounds of the formula (Ip) (=formula (I), in which m = 0, n = 1,
Y = —O—(CH2)2—O—; R3 = H, R4 = H;
R5 = H; R7, R9, R10 are each H and
aryl = phenyl which is substituted as shown in the table)
22
No.	Z	R6	R8	Phys. data
1342	3-F,5-Me	CF3	CHFCH3
1343	3,5-Me2	CH2F	CHFCH3
1344	H	Et	CF(CH3)2	oil
1345	H	Et	CH(CH3)2	oil
1346	H	Et	CHFCH3	oil
1347	3-F	H	CF2CHF2
1348	3-Cl	Pentyl	CF2CHF2
1349	3-F	c-Butyl	CHFCH3
1350	3,5-Me2	t-Butyl	i-Propyl
1351	3-Cl,5-Me	Me	CHFCF3
1352	3,5-Me2	H	CHFCH3
1353	3,5-Me2	H	Et
1354	3,5-Me2	H	CF(CH3)2
1355	H	Et	CF2CHF2
1356	3-F	c-Propyl	CF(CH3)2
1357	3-Cl	Et	CF(CH3)2
1358	H	c-Butyl	CF2CHF2
1359	3,5-F2	i-Propyl	1-Propyl
1360	3-CF3	c-Pentyl	CF3
1361	3-Me	Me	1-Propyl
1362	3-F	Me	CHFCH3
1363	3-F,5-OMe	CH2OMe	CF2CHF2
1364	3-Cl	Et	CF(CH3)2	oil
1365	3-Me	c-Propyl	1-Propyl
1366	3-Me	Et	CF2CHF2
1367	3-Cl	El	CF2CHF2
1368	H	c-Butyl	CF(CH3)2
1369	3-Me	c-Butyl	CF(CH3)2
1370	3,5-Me2	H	CH(CH3)2
1371	H	H	CF(CH3)2
1372	H	H	CH(CH3)2
1373	H	Et	Me
1374	3-Me,4-F	H	i-Propyl
1375	3-Me	c-Propyl	CHFCH3
1376	3-OMe	Me	CF3
1377	3,5-F2	c-Pentyl	CHFCH3
1378	3-CF3	i-Propyl	i-Propyl
1379	3-Cl	CH2OEt	CHFCH3
1380	H	CH2OMe	Me
1381	3-F	c-Butyl	CF2CHF2
1382	3-OMe	n-Butyl	CF2CHF2
1383	3,5-Me2	s-Butyl	CHFCH3
1384	3-F,5-OMe	CH2-c-Butyl	1-Propyl
1385	H	Me	CF(CH3)2	oil
1386	3-Me	CH2OMe	CF(CH3)2
1387	3-Me	Me	CF(CH3)2
1388	3-F	c-Propyl	CF2CHF2
1389	3,5-(OMe)2	CH2-c-Butyl	CF3
1390	3-F,5-OMe	CH2OEt	CHFCH3
1391	H	H	CHFCH3
1392	3-Me	Me	CF2CHF2
1393	3-Cl	Et	1-Propyl
1394	3-F	Et	CF(CH3)2
1395	H	Et	Et
1396	3-Me	Pentyl	CF2CHF2
1397	3,5-F2	Me	CF3
1398	3-OMe,5-Cl	i-Butyl	i-Propyl
1399	3-CF3	i-Butyl	CF2CHF2
1400	3-Cl	Me	CF2CHF2
1401	H	c-Propyl	CF(CH3)2
1402	3-Cl	c-Butyl	CF2CHF2
1403	3-OEt	CH2-c-Butyl	i-Propyl
1404	H	Me	1-Propyl	oil
1405	3-Me	Me	CHFCH3
1406	3-F	H	CF(CH3)2
1407	3-Me,4-F	Me	CF2CHF2
1408	3-Me	Et	CHFCH3
1409	3-F	Et	1-Propyl
1410	H	c-Propyl	CF2CHF2
1411	3-Cl	c-Propyl	CF(CH3)2
1412	H	s-Butyl	Me
1413	3-Me	c-Butyl	CHFCH3
1414	3-F	c-Butyl	CF(CH3)2
1415	3-OMe	c-Pentyl	CHFCH3
1416	3,5-(OMe)2	CH2OMe	CHFCH3
1417	3-OMe,5-Cl	H	CF(CH3)2
1418	3-OEt	CH2OEt	CHFCH3
1419	3-F,5-Me	t-Butyl	CF3
1420	3-CF3	Me	CF(CH3)2
1421	3-Me,4-F	Me	CF(CH3)2
1422	3-Me	c-Propyl	CF2CHF2
1423	3-OMe	Pentyl	1-Propyl
1424	3-Cl,5-Me	c-Pentyl	CHFCH3
1425	H	H	CHFCH3
1426	3-Cl	Me	CHFCH3
1427	3-Me	Et	1-Propyl
1428	H	c-Propyl	i-Propyl
1429	3-F	c-Propyl	CHFCH3
1430	3-Cl	c-Butyl	CHFCH3
1431	3,5-(OMe)2	CH2-cPropyl	CF(CH3)2
1432	3-OEt	i-Butyl	CF3
1433	3-Cl,5-Me	Hexyl	1-Propyl
1434	3-F,5-Me	H	CF(CH3)2
1435	H	Me	CF2CHF2
1436	3-Cl	c-Butyl	CF(CH3)2
1437	3-OMe,5-Cl	CH2F	i-Propyl
1438	3-Cl	Me	i-Propyl
1439	3-F	CH2OEt	CHFCH3
1440	3-Cl	c-Butyl	1-Propyl
1441	3-OMe,5-Cl	CF3	CF2CHF2
1442	3-F	c-Propyl	1-Propyl
1443	3,5-Me2	CF3	CF2CHF2
1444	3-F,5-OMe	CH2-c-Propyl	CF3
1445	3-F	Me	i-Propyl
1446	H	c-Propyl	CHFCH3
1447	3-F	H	i-Propyl
1448	H	H	i-Propyl
1449	3-Cl	Et	CHFCH3
1450	3-Me	c-Butyl	i-Propyl
1451	3,5-F2	n-Butyl	CF2CHF2
1452	3-Cl,5-Me	n-Butyl	CF2CHF2
1453	3-F	Me	CF2CHF2
1454	3-Me,4-F	Me	CHFCH3
1455	3-Me	c-Propyl	CF(CH3)2
1456	3-Cl	c-Propyl	i-Propyl

B. FORMULATION EXAMPLES

[0245] 1. Dusting Agent

[0246] A dusting agent is obtained by mixing 10 parts by weight of a compound of the formula (I) and 90 parts by weight of talc as inert substance and comminuting the mixture in a hammer mill.

[0247] 2. Dispersible Powder

[0248] A readily water-dispersible wettable powder is obtained by mixing 25 parts by weight of a compound of the formula (I), 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium ligninsulfonate and I part by weight of sodium oleoylmethyltaurinate as wetting agent and dispersant and grinding the mixture in a pinned disk mill.

[0249] 3. Dispersion Concentrate

[0250] A readily water-dispersible concentrate is obtained by mixing 20 parts by weight of a compound of the formula (I), 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, from about 255 to over 277° C.) and grinding the mixture in a ball mill to a fineness below 5 microns.

[0251] 4. Emulsifiable Concentrate

[0252] An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.

[0253] 5. Water-Dispersible Granules

[0254] Water-dispersible granules are obtained by mixing

75 parts by weight of a compound of the formula (I),
10 parts by weight of calcium ligninsulfonate,
5 parts by weight  of sodium lauryl sulfate,
3 parts by weight  of polyvinyl alcohol and
7 parts by weight  of kaolin,

[0255] grinding the mixture in a pinned disk mill and granulating the powder in a fluidized bed by spraying on water as granulation liquid.

[0256] Water-dispersible granules are also obtained by homogenizing and precomminuting

25	parts by weight	of a compound of the formula (I),
5	parts by weight	of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate,
2	parts by weight	of sodium oleoylmethyltaurinate,
1	part	of polyvinyl alcohol,
17	parts	of calcium carbonate and
50	parts	of water,

[0257] in a colloid mill, followed by grinding in a bead mill, and atomizing and drying the resulting suspension in a spray tower using a single-substance nozzle.

C. BIOLOGICAL EXAMPLES

[0258] 1. Pre-Emergence Action Against Weeds

[0259] Seeds of mono- and dicotyledonous weed plants are placed in sandy loam soil in cardboard pots and covered with soil. The novel compounds, formulated as wettable powders or emulsion concentrates, are then applied to the surface of the soil cover in the form of an aqueous suspension or emulsion at an application rate of from 600 to 800 l of water/ha (converted), in various dosages. After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the weeds. After the test plants have emerged after a trial period of 3 to 4 weeks, the damage to the plants or the negative effect on emergence is rated visually by comparison with untreated controls. As shown by the test results, the novel compounds have good herbicidal pre-emergence activity against a broad spectrum of weed grasses and broad-leaved weeds. For example, the compounds of Example Nos. 41, 42, 64, 76, 78, 120, 167, 183, 201, 207, 213, 220, 222, 228, 231, 245, 253, 281, 282, 297, 299, 300, 303, 305, 308, 311, 326, 329, 336, 339, 340, 347, 358, 368, 369, 370, 372, 376, 380, 381, 384, 394, 490, 501, 502, 510, 528, 531, 532, 553, 554, 582, 598, 605, 609, 618, 626, 636, 645, 681, 696, 698, 869, 870, 926, 930, 987, 1005, 1234, 1235, 1236, 1251, 1252, 1253, 1307, 1344, 1345, 1346, 1364, 1385 and 1404 show good and in most cases very good herbicidal activity against harmful plants such as Stellaria media, Amaranthus retroflexus, Sinapis avreuse, Avena fatura, Lolium multiflorum and Setaria viridis at an application rate of 3.0 kg or less of active substance per hectare.

[0260] 2. Post-Emergence Action Against Weeds

[0261] Seeds of mono- and dicotyledonous weeds are placed in sandy loam soil in cardboard pots, covered with soil and cultivated in a greenhouse under good growth conditions. Two to three weeks after sowing, the test plants are treated at the three-leaf stage. The novel compounds, formulated as wettable powders or emulsion concentrates, are sprayed in various dosages onto the green parts of the plant at an application rate of from 600 to 8001 of water/ha (converted), and, after the test plants have remained in the greenhouse for 3 to 4 weeks under optimum growth conditions, the action of the preparations is rated visually by comparison with untreated controls. The novel compositions also have good post-emergence herbicidal activity against a broad spectrum of economically important weed grasses and broad-leaved weeds. For example, the compounds of Example Nos. 20, 23, 41, 42, 43, 46, 78, 80, 183, 184, 201, 207, 213, 220, 222, 228, 231, 245, 253, 281, 297, 299, 303, 305, 308, 311, 326, 336, 340, 347, 358, 368, 369, 370, 372, 376, 380, 381, 384, 490, 501, 502, 510, 528, 531, 532, 553, 554, 582, 598, 605, 609, 618, 626, 636, 645, 681, 696, 698, 869, 870, 926, 930, 987, 1005, 1234, 1235, 1236, 1251, 1252, 1253, 1307, 1344, 1345, 1346, 1364, 1385 and 1404 show good and in most cases very good herbicidal activity against harmful plants such as Stellaria media, Amaranthus retroflexus, Sinapis avreuse, Avena fatura, Lolium multiflorum and Setaria viridis, at an application rate of 3.0 kg or less of active substance per hectare.

[0262] 3. Action on Weeds in Rice

[0263] Typical rice weeds such as Echinocloa crus galli and Cyperus iria are cultivated in a greenhouse under paddy rice conditions (dammed height of water: 2-3 cm). After the treatment, the test plants are set up in a greenhouse under optimum growth conditions and are maintained in this way under these conditions throughout the test period. About three weeks after application, evaluation is made by visual rating of the damage to the plants by comparison with untreated controls. The compounds according to the invention have very good herbicidal activity against harmful plants. For example, the compounds of Example Nos. 41, 42, 46, 120, 183, 201, 207, 213, 220, 222, 228, 231, 245, 253, 281, 299, 300, 303, 308, 311, 326, 336, 340, 347, 358, 368, 369, 370, 372, 376, 380, 381, 384 and 394 show very good herbicidal activity against Cyperus iria and Echinocloa crus-galli.

[0264] 4. Tolerance by Crop Plants

[0265] In further greenhouse experiments, seeds of a relatively large number of crop plants and weeds are placed in sandy loam soil and covered with soil. Some of the pots are treated immediately as described under section 1, while the remainder are placed in a greenhouse until the plants have developed two to three true leaves, and then sprayed with various dosages of the novel substances of the formula (I), as described in section 2. Four to five weeks after the application, and after the plants have remained in the greenhouse, visual rating shows that the compounds according to the invention leave dicotyledonous crops such as, for examle, soya and sugar beet undamaged or almost undamaged when employed pre- and post-emergence, even when high dosages of active compound are used. Moreover, some substances also leave gramineous crops unharmed, for example barley, wheat and rice. Some of the compounds of the formula (I) display a high selectivity and are therefore suitable for controlling unwanted plant growth in agricultural crops.

Claims

1. A compound of the formula I, if appropriate also in its salt form,

2. The compound as claimed in claim 1, wherein aryl is an unsubstituted or substituted mono- or bicyclic aromatic radical having 5 to 10 ring atoms, 1, 2, 3 or 4 of which may in each case independently of one another originate from the group consisting of oxygen, sulfur and nitrogen; —Y— is a divalent unit from the group consisting of —O—, —S—, —NR11—, —NR12CONR13—, —CO2—, —OCONR14—, —SO—, —SO2—, —SO2O—, —SO2NR14—, —O—NR11—, —NH—NH— and —O—CRaRb—CRcRd—O—, in which Ra, Rb, Rc and Rd independently of one another are each H, CH3 or C2H5, or else a trivalent unit of the formula —O—N═ and R1, R2 independently of one another are each a radical from a group G3 which comprises hydrogen, (C1-C8)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C6)-alkoxy, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkoxy, aryl-(C1-C6)-alkyl and (C3-C8)-cycloalkyl-(C1-C6)-alkyl, where the cyclic moiety of the four last-mentioned radicals is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, where —B— and X1 are as defined below, and where the non-cyclic moiety of the eight last-mentioned radicals from the group G3 is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X2, where X2 is as defined below, and where the non-cyclic moiety of the radicals from the group G3 may in each case be interrupted by one or more identical or different heteroatoms from the group consisting of oxygen and sulfur, or R1 and R2 in a (CR1R2) group form, together with the carbon atom which carries them, a carbonyl group, a group CR15R16 or 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, or two R1 of two directly adjacent or not directly adjacent (CR1R2) groups form, together with the carbon atoms which carry or link them, an unsubstituted or substituted 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, or two R1 of two directly adjacent (CR1R2) groups together with the bond between the carbon atoms of the groups form a double bond, or two R1 and two R2 of two directly adjacent (CR1R2) groups together with the bond between the carbon atoms of the groups form a triple bond or R1 is a linkage point for the double bond in the case where Y is a trivalent unit ═N—O— adjacent to a CR1R2 group, and R3 and R4 independently of one another are each a radical from a group G4 which comprises hydrogen, (C1-C8)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C6)-alkoxy, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkoxy, aryl, aryl-(C1-C6)-alkyl, aryl-(C1-C6)-alkoxy, (C3-C8)-cycloalkyl-(C1-C6)-alkyl, (C3-C8)-cycloalkyl-(C1-C6)-alkoxy, (C3-C8)-cycloalkoxy-(C1-C6)-alkyl and (C3-C8)-cycloalkoxy-(C1-C6)-alkoxy, where the cyclic moiety of the nine last-mentioned radicals is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato and —B—X1, where —B— and X1 are as defined below, and where the non-cyclic moiety of the thirteen last-mentioned radicals from the group G4 is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato and —B—X2, where X2 is as defined below, and where the non-cyclic moiety of the radicals from the group G4 may in each case be interrupted by one or two identical or different heteroatoms from the group consisting of oxygen and sulfur, or R3 and R4 together with the carbon atom which carries them form a carbonyl group, a group CR15R16 or a 3- to 6-membered ring, which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, or two R3 of two directly adjacent or not directly adjacent (CR3R4) groups form, together with the carbon atoms which carry or link them, an unsubstituted or substituted 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1; or two R3 of two directly adjacent (CR3R4) groups together with the bond between the carbon atoms of the groups form a double bond, or two R3 and two R4 of two directly adjacent (CR3R4) groups together with the bond between the carbon atoms of the groups form a triple bond or R3 is a linkage point for the double bond in the case where Y is a trivalent unit ═N—O— adjacent to a CR3R4 group, and —B— is a direct bond or a divalent unit from the group consisting of —O—, —S—, —NR11—, —CO—, —CO2—, —OCO2—, —SO—, —SO2—, —SO2O— und —SO2NR14—; X1 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl or heterocyclyl having 3 to 6 ring atoms, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen and sulfur, and where the five last-mentioned radicals are unsubstituted or substituted by one or more identical or different halogen atoms, X2 is hydrogen or heterocyclyl having 3 to 9 ring atoms, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen and sulfur and which is unsubstituted or substituted by 1, 2 or 3 identical or different halogen atoms, R5, R6 independently of one another are each a radical from the group G4, or R3 and R5 of two directly adjacent or not directly adjacent (CR3R4)— or (CR5R6)— groups together with the carbon atoms which link them form an unsubstituted or substituted 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, or R5 and R6 together with the carbon atom which carries them form a carbonyl group, a group CR15R16 or a 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, or R6 is heterocyclyl and R7 is hydrogen, amino, alkylcarbonyl, alkylamino or dialkylamino having in each case one to four carbon atoms in the alkyl radical, is an acyclic or cyclic hydrocarbon radical having in each case one to six carbon atoms, or is heterocyclyl having three to six ring atoms and one to three hetero ring atoms from the group consisting of nitrogen, oxygen and sulfur, where each of the six last-mentioned radicals is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, (C1-C4)-alkoxy, halo-(C1-C4)-alkoxy, (C1-C4)-alkylthio, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-alkenyloxy, (C2-C4)-alkynyloxy, hydroxyl, amino, alkylamino, dialkylamino, nitro, carboxyl, cyano, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl, formyl, carbamoyl, mono- and di-(C1-C4)-alkylaminocarbonyl, (C1-C4)-alkylsulfonyl, halo-(C1-C4)-alkylsulfonyl and, in the case of cyclic radicals, also (C1-C4)-alkyl and halo-(C1-C4)-alkyl, R8 is (C1-C6)-alkyl, which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, cyano, nitro, thiocyanato, hydroxyl, (C1-C4)-alkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylsulfonyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, phenyl, (C3-C9)-cycloalkyl, (C3-C9)-cycloalkoxy and heterocyclyl having three to six ring atoms and one to three hetero ring atoms from the group consisting of oxygen, nitrogen and sulfur which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, amino, (C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy, is (C3-C8)-Cycloalkyl or (C3-C8)-cycloalkoxy, where the two last-mentioned radicals are unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, (C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy, R9, R10 independently of one another are each hydrogen, amino, (C1-C6)-alkylcarbonyl, (C1-C6)-alkylamino, di-[(C1-C6)-alkyl]amino, (C1-C6)-alkyl, (C3-C8)-cycloalkyl, (C1-C6)-alkoxy, (C3-C8)-cycloalkoxy or heterocyclyl having 3 to 6 ring atoms and 1 to 3 hetero ring atoms from the group consisting of oxygen, nitrogen and sulfur, where each of the eight last-mentioned radicals is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, amino, hydroxyl and, in the case of cyclic radicals, also (C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy, or R9 and R10 together with the nitrogen atom which carries them form a heterocycle having a total of three to six ring atoms and among these one to four hetero ring atoms, where the other hetero ring atoms which may be present in addition to the nitrogen atom that is present are selected from the group consisting of oxygen, nitrogen and sulfur and where this heterocycle is unsubstituted or substituted by up to three identical or different radicals from the group consisting of halogen, amino, hydroxyl, (C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy; and R11 is hydrogen, amino, (C1-C6)-alkylamino, di-[(C1-C6)-alkyl]amino, (C1-C6)-alkyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkoxy, (C1-C6)-alkoxy-(C1-C6)-alkoxy, (C3-C8)-cycloalkoxy, (C1-C6)-alkylcarbonyl, where the nine last-mentioned radicals are unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, amino, hydroxyl and, in the case of cyclic radicals, also (C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy, R12, R13 independently of one another are each hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, phenyl, phenyl-(C1-C6)-alkyl, (C3-C8)-cycloalkyl, (C1-C8)-cycloalkyl-(C1-C6)-alkyl, where the cyclic moiety of the four last-mentioned radicals is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of (C1-C4)-alkyl, halo-(C1-C4)-alkyl, (C1-C4)-alkoxy and halo-(C1-C4)-alkoxy, or R12 and R13 together with the N—CO—N group which carries them form a 5- to 8-membered ring which, in addition to the two abovementioned nitrogen atoms, may contain a further heteroatom from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, (C1-C4)-alkyl and halo-(C1-C4)-alkyl; and R14 is hydrogen or (C1-C6)-alkyl or (C3-C8)-cycloalkyl, each of which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, phenyl, hydroxyl, (C1-C4)-alkoxy and halo-(C1-C4)-alkoxy and R15 and R16 independently of one another are each hydrogen, phenyl, (C1-C6)-alkoxy, phenyl-(C1-C6)-alkyl, (C1-C6)-alkyl, (C1-C6)-alkylthio, where the five last-mentioned radicals are unsubstituted or substituted, and where the aliphatic carbon skeleton of the three last-mentioned radicals may be interrupted by one or more identical or different heteroatoms from the group consisting of oxygen and sulfur, or R15 and R16 together with the carbon atom which carries them form a 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, (C1-C4)-alkyl and halo-(C1-C4)-alkyl.

3. The compound as claimed in claim 1, wherein aryl is a mono- or bicyclic aromatic radical having 5 to 10 ring atoms, 1, 2, 3 or 4 of which may in each case independently of one another originate from the group consisting of oxygen, sulfur and nitrogen, which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, hydroxyl, amino, formyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl, halo-(C1-C4)-alkoxycarbonyl, halo-(C1-C4)-alkylcarbonyl, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkoxy, (C1-C4)-alkoxy-(C1-C4)-alkyl, halo-(C1-C4)-alkoxy-(C1-C4)-alkyl, halo-(C1-C4)-alkoxy-[halo-(C1-C4)-alkyl], (C1-C4)-alkoxy-[halo-(C1-C4)-alkyl], (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C4)-alkyl, (C3-C6)-cycloalkyl-[halo-(C1-C4)-alkyl], halo-(C3-C6)-cycloalkyl-[halo-(C1-C4)-alkyl], halo-(C3-C6)-cycloalkyl-(C1-C4)-alkyl, (C1-C6)-alkylamino, di-[(C1-C6)-alkyl]amino, (C1-C6)-alkylaminocarbonyl, aminosulfonyl, (C1-C6)-alkylaminosulfonyl, di-[(C1-C6)-alkyl]aminosulfonyl, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy, —Y— is a divalent unit from the group consisting of —O—, —S—, —NR11—, —CO2—, —SO—, —SO2—, —SO2O—, —SO2NR14—, —NH—CO—NH—, —OCONH—, —O—NH— and —OCH2CH2—O— or a trivalent unit —O—N═, R1, R2 independently of one another are in each case a radical from a group G5 which comprises hydrogen, (C1-C6)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C6)-alkoxy, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkoxy, aryl-(C1-C6)-alkyl and (C3-C6)-cycloalkyl-(C1-C6)-alkyl, where the cyclic moiety of the four last-mentioned radicals is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, where —B— and X1 are as defined below, and where the non-cyclic moiety of the eight last-mentioned radicals from the group G5 is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X2, where X2 is as defined below, and where the non-cyclic moiety of the radicals from the group G5 may in each case be interrupted by one or more identical or different heteroatoms from the group consisting of oxygen and sulfur, or R1 and R2 of a (CR1R2) group form, together with the carbon atom that carries them, a carbonyl group, a group CR15R16 or 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, or two R1 of two directly adjacent or not directly adjacent (CR1R2) groups form, together with the carbon atoms that carry or link them, an unsubstituted or substituted 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, or two R1 of two directly adjacent (CR1R2) groups together with the bond between the carbon atoms of the groups form a double bond, or two R1 and two R2 of two directly adjacent (CR1R2) groups together with the bond between the carbon atoms of the groups form a triple bond, or R1 is a linkage point for the double bond in the case where Y is a trivalent unit ═N—O— adjacent to a CR1R2 group, R3, R4 independently of one another are in each case a radical from a group G6 which comprises hydrogen, (C1-C6)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C6)-alkoxy, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkoxy, aryl, aryl-(C1-C4)-alkyl, aryl-(C1-C4)-alkoxy, (C3-C8)-cycloalkyl-(C1-C4)-alkyl, (C3-C8)-cycloalkyl-(C1-C4)-alkoxy, (C3-C8)-cycloalkoxy-(C1-C4)-alkyl and (C3-C8)-cycloalkoxy-(C1-C4)-alkoxy, where the cyclic moiety of the nine last-mentioned radicals is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, where —B— and X1 are as defined below, and where the non-cyclic moiety of the thirteen last-mentioned radicals from the group G6 is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X2, where X2 is as defined below, and where the non-cyclic moiety of the radicals from the group G6 may in each case be interrupted by a heteroatom from the group consisting of oxygen and sulfur, or R3 and R4 together with the carbon atom that carries them form a carbonyl group, a group CR15R16 or a 3- to 6-membered ring, which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, or two R3 of two directly adjacent or not directly adjacent (CR3R4) groups form, together with the carbon atoms that carry or link them, an unsubstituted or substituted 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, or two R3 of two directly adjacent (CR3R4) groups together with the bond between the carbon atoms of the groups form a double bond, or two R3 and two R4 of two directly adjacent (CR3R4) groups together with the bond between the carbon atoms of the groups form a triple bond or R3 is a linkage point for the double bond in the case where Y is a trivalent unit ═N—O— adjacent to a CR3R4 group, and —B— is a direct bond or a divalent unit from the group consisting of —O—, —S—, —NR11—, —CO—, —CO2—, —SO—, —SO2— and —SO2NR4—, X1 is hydrogen, (C1-C6)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C6)-cycloalkyl or heterocyclyl having 3 to 6 ring atoms, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen and sulfur, and where the five last-mentioned radicals are unsubstituted or substituted by up to five identical or different halogen atoms, X2 is hydrogen or heterocyclyl having 3 to 6 ring atoms, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen and sulfur, which is unsubstituted or substituted by 1, 2 or 3 identical or different halogen atoms, R5, R6 independently of one another are each a radical of the group G6, or R3 and R5 of two directly adjacent or not directly adjacent (CR3R4)— or (CR5R6)— groups form, together with the carbon atoms which link them, an unsubstituted or substituted 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, or R5 and R6 together with the carbon atom which carries them form a carbonyl group, a group CR15R16 or a 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato and —B—X1, or R6 is heterocyclyl and R7 is hydrogen, amino, alkylcarbonyl, alkylamino or dialkylamino having in each case one to four carbon atoms in the alkyl radical, or is an acyclic or cyclic hydrocarbon radical having in each case one to six carbon atoms, where each of the five last-mentioned radicals is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, (C1-C4)-alkoxy, halo-(C1-C4)-alkoxy, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-alkenyloxy, (C2-C4)-alkynyloxy, hydroxyl, amino, (C1-C4)-alkylamino, di-[(C1-C4)-alkyl]amino, nitro, carboxyl, cyano, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl, formyl, carbamoyl, (C1-C4)-alkylsulfonyl, halo-(C1-C4)-alkylsulfonyl and, in the case of cyclic radicals, also (C1-C4)-alkyl and halo-(C1-C4)-alkyl, R8 is (C1-C6)-alkyl which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, cyano, hydroxyl, (C1-C4)-alkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylsulfonyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, phenyl, (C3-C9)-Cycloalkyl, (C3-C9)-cycloalkoxy, is (C3-C8)-cycloalkyl or (C3-C8)-cycloalkoxy, where the two last-mentioned radicals are substituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, (C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy, R9, R10 independently of one another are each hydrogen, amino, (C1-C4)-alkylcarbonyl, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C1-C4)-alkyl, (C3-C8)-cycloalkyl, (C1-C4)-alkoxy, (C3-C8)-cycloalkoxy or heterocyclyl having 3 to 6 ring atoms and 1 to 3 hetero ring atoms from the group consisting of oxygen, nitrogen and sulfur, where each of the eight last-mentioned radicals is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen, amino, hydroxyl and, in the case of cyclic radicals, also (C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy, or R9 and R10 together with the nitrogen atom which carries them form a heterocycle having a total of three to six ring atoms and from among these one to four hetero ring atoms, where the other hetero ring atoms which may be present in addition to the nitrogen atom that is present are selected from the group consisting of oxygen, nitrogen and sulfur and where this heterocycle is unsubstituted or substituted; R11 is hydrogen, amino, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C1-C4)-alkyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkyl-(C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C3-C8)-cycloalkoxy, (C1-C4)-alkylcarbonyl, where the nine last-mentioned radicals are unsubstituted or substituted by one or more identical or different halogen atoms and, in the case of cyclic radicals, also (C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkyl and halo-(C1-C4)-alkoxy, R14 is hydrogen or (C1-C4)-alkyl or (C3-C6)-cycloalkyl, each of which is optionally substituted by one or more identical or different radicals from the group consisting of halogen, (C1-C4)-alkoxy and halo-(C1-C4)-alkoxy and R15, R16 independently of one another are each hydrogen, phenyl, (C1-C4)-alkoxy, phenyl-(C1-C4)-alkyl, (C1-C4)-alkyl, (C1-C4)-alkylthio, where the five last-mentioned radicals are unsubstituted or substituted by one or more identical or different halogen atoms and, in the case of cyclic radicals, also by one or more identical or different radicals from the group consisting of halogen, (C1-C4)-alkyl and halo-(C1-C4)-alkyl, or R15 and R16 together with the carbon atom which carries them form a 3- to 6-membered ring which may contain one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen, (C1-C4)-alkyl and halo-(C1-C4)-alkyl.

4. The compound as claimed in claim 1, wherein aryl is phenyl, naphthyl, pyridinyl, pyrimidinyl, furanyl, benzofuranyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, oxadiazolyl or thienyl, each of which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, hydroxyl, amino, formyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkoxy, (C1-C4)-alkylamino, di-[(C1-C4)-alkyl]amino, aminocarbonyl, (C1-C4)-alkylaminocarbonyl, di-[(C1-C4)-alkyl]aminocarbonyl, aminosulfonyl, (C1-C4)-alkylaminosulfonyl, di-[(C1-C4)-alkyl]aminosulfonyl, halo-(C1-C4)-alkyl, halo-(C1-C4)-alkoxy, (C1-C2)-alkylthio, (C1-C2)-alkylsulfinyl, (C1-C2)-alkylsulfonyl, halo-(C1-C2)-alkylthio, halo-(C1-C2)-alkylsulfinyl and halo-(C1-C2)-alkylsulfonyl, —Y— is a divalent unit from the group consisting of —O—, —S—, —NR11—, —CO2—, —SO—, —SO2—, —NH—CO—NH—, —O—CONH—, —O—NH— and —OCH2CH2O— or a trivalent unit of the formula —O—N═, m is 0, 1, 2 or 3, n is 1, 2, 3, 4 or 5, R1, R2 independently of one another are each a radical from a group G7 which comprises (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkoxy, hydrogen, (C3-C6)-cycloalkyl, where the last-mentioned radical is unsubstituted or substituted by one to four identical or different radicals from the group consisting of halogen and —B—X1, and where the four first-mentioned radicals from the group G7 are unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen and —B—X2, where X2 is as defined below, or R1 and R2 of a (CR1R2) group form together with the carbon atom which carries them a carbonyl group, or two R1 of two directly adjacent or not directly adjacent (CR1R2) groups form, together with the carbon atoms which carry or link them, a 3-, 5- or 6-membered ring which may contain up to two heteroatoms from the group consisting of oxygen, sulfur and nitrogen and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen and —B—X1, or R1 is a linkage point for the double bond in the case where Y is a trivalent unit ═N—O— which is adjacent to a CR1R2 group, and R3, R4 independently of one another are each a radical from a group G8 which comprises hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C6)-alkoxy, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkoxy, aryl, aryl-(C1-C2)-alkyl, aryl-(C1-C2)-alkoxy, (C3-C6)-cycloalkyl-(C1-C2)-alkyl and (C3-C8)-cycloalkoxy-(C1-C4)-alkyl, where the cyclic moiety of the seven last-mentioned radicals is in each case unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X1, where —B— and X1 are as defined below, and where the non-cyclic moiety of the eleven last-mentioned radicals from the group G8 is in each case unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and —B—X2, where X2 is as defined below, or R3 and R3 of a (CR3R4) group form together with the carbon atom which carries them a carbonyl group, or two R3 of two directly adjacent or not directly adjacent (CR3R4) groups form, together with the carbon atoms which carry or link them, a 3-, 5- or 6-membered ring which may contain up to two heteroatoms from the group consisting of oxygen, sulfur and nitrogen and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen and —B—X1, or R3 is a linkage point for the double bond in the case where Y is a trivalent unit ═N—O— which is adjacent to a CR3R4 group, and —B— is a direct bond or a divalent unit from the group consisting of —O—, —S—, —NR11—, —CO— and —CO2—; X1 is hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or (C3-C6)-cycloalkyl, the four last-mentioned radicals of which are unsubstituted or substituted by up to five identical or different halogen atoms, X2 is hydrogen or heterocyclyl having 3 to 6 ring atoms, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen and sulfur and which is unsubstituted or substituted by one or more identical or different halogen atoms, R5 is hydrogen, (C1-C4)-alkyl, halo-(C1-C4)-alkyl or (C3-C6)-cycloalkyl, or R3 and R5 of two directly adjacent or not directly adjacent (CR3R4)— or (CR5R6) groups form, together with the carbon atoms which link them, a 3-, 5- or 6-membered ring which may contain up to two heteroatoms from the group consisting of oxygen, sulfur and nitrogen and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen and —B—X1, and R6 is hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkoxy, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C4)-alkyl, (C3-C6)-cycloalkoxy-(C1-C4)-alkyl, (C3-C6)-cycloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkyl or halo-(C1-C4)-alkyl, R7 is hydrogen, amino or (C1-C4)-alkyl, R8 is (C1-C4)-alkyl, halo-(C1-C4)-alkyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl or (C3-C6)-cycloalkyl-(C1-C4)-alkyl, R9, R10 independently of one another are each hydrogen, amino, formyl or (C1-C4)-alkyl, or R9 and R10 together with the nitrogen atom which carries them form a heterocycle having three to six ring atoms and one to two hetero ring atoms, where the other hetero ring atoms which may be present in addition to the nitrogen atom which is present are selected from the group consisting of oxygen and nitrogen, R11 is hydrogen, amino, (C1-C4)-alkylamino, di-[(C1-C4)-alkyl]amino, (C1-C4)-alkyl or (C3-C6)-cycloalkyl, where the five last-mentioned radicals are unsubstituted or substituted by one or more identical or different halogen atoms, and R14 is hydrogen or (C1-C4)-alkyl.

5. A process for preparing a compound of the formula I or a salt thereof as claimed in claim 1, which comprises a) reacting a compound of the formula (II) R8-Fu  (II) in which Fu is a functional group from the group consisting of carboxylic ester, carboxylic orthoester, carbonyl chloride, carboxamide, carboxylic anhydride and trichloromethyl with a biguanidide of the formula (III) or an acid addition salt thereof 24or b) reacting a compound of the formula (IV) 25in which Z1 is an exchangeable radical or a leaving group, for example chlorine, trichloromethyl, (C1-C4)-alkylsulfonyl and unsubstituted or substituted phenyl-(C1-C4)-alkylsulfonyl or (C1-C4)-alkylphenylsulfonyl, with a suitable amine of the formula (V) or an acid addition salt thereof 26where in the formulae (II), (III), (IV) and (V) the radicals R1 to R10, Y and n and m are as defined under formula (I).

6. A herbicidal or plant growth-regulatory composition, which comprises one or more compounds of the formula I or salts thereof as claimed in claim 1, if appropriate in a mixture with formulation auxiliaries.

7. A method for controlling undesirable plants or for regulating the growth of plants, wherein an effective amount of one or more compounds of the formula I or salts thereof as claimed in claim 1 is applied to the plants or to the location of the undesirable vegetation or to the area under cultivation.

8. The method as claimed in claim 7, wherein the compounds of the formula I or salts thereof are employed for controlling undesirable plants or for regulating the growth of plants in crops of useful plants.

9. The method as claimed in claim 8, wherein the useful plants are transgenic useful plants.