CZ20004366A3 - Substituted 2,4-diamino-1,3,5-triazines, process for their preparation and their use as herbicides and growth regulators - Google Patents

Abstract

The solution relates to substituted 2,4-diamino-1,3,5-triazines of general formula 1, in which the substituents have a specific meaning, a method of their production and their use as herbicides and plant growth regulators, especially herbicides for selective control of weeds and weedy grasses in crops of useful plants.

Description

Substituted 2,4-diamino-1,3,5-triazines, their production process and their use as herbicides and growth regulators

Technical area

The invention relates to the technical field of herbicides and plant growth regulators, in particular herbicides for the selective control of weeds and weedy grasses in crops of useful plants.

State of the art

It is already known from various publications 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 linked to an amino group via an ethylene, oxyethylene, aminoethylene, thioethylene or propylene chain. WO 97/08156 describes

2,4-diamino-1,3,5-triazines in which the phenyl radical is bonded to the amino group via an alkylene, alkenylenemethyl or alkynylenemethyl chain. WO 98/15537 discloses

2,4-diamino-1,3,5-triazines which carry an aromatic or heterocyclic residue on the amino group via a propylene or oxyethylene chain. Finally, WO 98/15539 discloses

2,4-diamino-1,3,5-triazines which carry a benzyl, naphthylmethyl, heterocyclyl or heterocyclyloxy radical on the amino group via an ethylene chain.

However, the use of the 2,4-diamino-1,3,5-triazines known from these documents is associated with disadvantages in practice. Thus, the herbicidal or plant growth regulating activity of these known compounds is not always sufficient, or, with sufficient herbicidal activity, undesirable damage to useful plants is observed.

The object of the present invention is therefore to find herbicidal and growth-regulating active substances of the type

2,4-diamino-1,3,5-triazines which would overcome the disadvantages known from the prior art.

The essence of the invention

The subject of the present invention are 2,4-diamino-1,3 5-triazines of the general formula I, optionally in the form of their salts.

N-R

Aryl· • (CR ¹ R\ - Y - (CR ³ R ⁴ ) _n — CR ⁵ — NR ⁷ — (O in which

Aryl denotes an optionally substituted monocyclic or bicyclic aromatic radical with 5 to 14 ring atoms, of which 1, 2, 3 or 4 may independently be from the group consisting of oxygen, sulfur and nitrogen,

-Y- denotes a divalent unit from the group including -O-,

-S-, -NR ²² -, -NR ²² CONR ²³ -, -C02-, -OC02-, -OC0NR ¹⁴ -, -SO-, -SO2-, -S0 ₂ 0-, -OS0 ₂ 0- and -S0 ₂ NR ²⁴ -, or also from the group comprising -O-NR ²² -, -NR'-NR'', wherein

R' and R'' are independently defined as R ²⁴ , and - (Y' -CR ^a R ^b -CR ^c R ^d );-Y'' , wherein

Y' and Y'' independently represent an oxygen atom, a sulfur atom or an N-alkyl group with 1 to 4 carbon atoms,

R ^a , R ² *, R ^c and R* ² independently of one another denote a hydrogen atom or an alkyl group with 1 to 4 carbon atoms and a i denotes an integer from 1 to 5, preferably 1, but also a trivalent unit of the formula -O-N= , m denotes the number 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2 or 3, n denotes an integer from 1 to 10, preferably 1 to 5, in particular

1, 2, 3 or 4, with the proviso that n does not represent 1 when m represents zero and Y represents the group -0-, -S-,

-SO-, -S0 ₂ ~ or -NR ²² - ,

9

R and R each independently denote a residue of the group G1 comprising a hydrogen atom, an alkyl group with 1 to carbon atoms, an alkenyl group with 2 to 8 carbon atoms, an alkynyl group with 2 to 8 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkoxy group with 3 to 8 carbon atoms, an arylalkyl group with 1 to 6 carbon atoms in the alkyl and a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the alkyl, wherein the cyclic parts of the four latter-mentioned residues are optionally substituted by one or more, identical or different residues from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a -BX^ group, wherein -B- and X^ are defined below and wherein the non-cyclic parts of the eight latter-mentioned residues are the named residues of the group GI are optionally substituted by one or more, identical or different residues from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a -BX group, wherein -B and X are defined below and wherein the non-cyclic parts of the residues of the group GI may be interrupted by one or more, identical or different heteroatoms from the group comprising an oxygen atom and a sulfur atom, or

12

R and R groups (CR R ) form with the carbon atom carrying it a carbonyl group, a group CrI^rIů _ne 5 _o a three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group comprising an oxygen, nitrogen and sulfur atom and is optionally substituted by one or more, the same or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a -BX^ group, or

12 two R- ¹ - two directly or indirectly adjacent groups (CR R ) form with the carbon atoms carrying them or connecting them • · an optionally substituted three- to six-membered ring, which optionally contains one or two identical or different heteroatoms from the group comprising an oxygen, nitrogen and sulfur atom and which is optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a -BX ⁴ group, or

12 two R of two directly adjacent groups (CR R ) together with the bond between the carbon atoms of the groups denotes a double 1 2 bond or two R and two R of two directly adjacent groups (CR R ) together with the bond between the carbon atoms of the groups denotes a triple bond, or also

R ⁴ indicates the binding site for the double bond in the case where 1 2

Y denotes the trivalent unit =N-0- adjacent to the CR R group,

R ³ , R ⁴ each independently represents a residue of the group G2, comprising a hydrogen atom, an alkyl group with 1 to carbon atoms, an alkenyl group with 2 to 8 carbon atoms, an alkynyl group with 2 to 8 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, an alkylthio group with 1 to 10 carbon atoms, an alkylsulfinyl group with 1 to 10 carbon atoms, an alkylsulfonyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkoxy group with 3 to 8 carbon atoms, an aryl group, an arylalkyl group with 1 to 6 carbon atoms in the alkyl, an arylalkoxy group with 1 to 6 carbon atoms in the alkoxy, a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with up to 6 carbon atoms in the alkyl, a cycloalkylalkoxy group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the alkoxyl, a cycloalkoxyalkyl group with 3 to 8 carbon atoms in the cycloalkoxyl and with 1 to 6 carbon atoms in the alkyl and a cycloalkoxyalkoxyl group with 3 to 8 carbon atoms in the cycloalkoxyl and with 1 to 6 carbon atoms in the alkoxyl, wherein the cyclic part of the nine latter-mentioned radicals is optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a -BX^ group, wherein -B- and X ³ are defined below and wherein the non-cyclic part of the sixteen latter-mentioned radicals of the group G2 is optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a group -BX , wherein X is defined below and wherein the non-cyclic part of the residues of the group G2 may be interrupted by one or more, identical or different, heteroatoms from the group consisting of oxygen and sulfur, or

R ³ and R ⁴ form with the carbon atom carrying them a carbonyl group, a CR^R^ group or a three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group comprising an oxygen, nitrogen and sulfur atom and is optionally substituted by one or more, the same or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and the group -BX*· , or two R° of two directly or indirectly adjacent groups (CR ^J R ) form with the carbon atoms carrying them, optionally connecting them an optionally substituted three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group comprising an oxygen, nitrogen and sulfur atom and which is optionally substituted by one or more, the same or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and the group -BX ⁴ , or also

QQA two R ^J of two directly adjacent groups (CR R ) together with the bond between the carbon atoms of the groups denote a double bond or two R^ and two R ⁴ of two directly adjacent groups (Cr3r4) together with the bond between the carbon atoms of the groups denote a triple bond, or

R denotes the binding site for the double bond in the case where

Y denotes the trivalent unit -0-N= adjacent to the CR R group,

-B- denotes a direct bond or a divalent unit from the group consisting of -0-, -S-, -NrH-, -NrI^coNR^-, -C0 ₂ -, -OC0 ₂ -, -OC0NR ¹⁴ -, -S0-, -S0 ₂ -, -S0 ₂ 0-, -OS0 ₂ 0- and -so ₂ nr ¹⁴ - , χΐ denotes a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, an alkenyl group with 2 to 8 carbon atoms, an alkynyl group with 2 to 8 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms or a heterocyclyl group with 3 to 9 ring atoms, of which 1, 2 or 3 come from the group consisting of a nitrogen, oxygen and sulphur atom and wherein the five latter radicals are optionally substituted by one or more, the same or different halogen atoms, denotes a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, an alkenyl group with 2 to 8 carbon atoms, an alkynyl group with 2 to 8 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms or a heterocyclyl group with 3 to 9 ring atoms, of which 1, 2 or 3 are from the group consisting of nitrogen, oxygen and sulphur, the five latter radicals being optionally substituted by one or more, identical or different, halogen atoms, and

X represents a hydrogen atom or a heterocyclyl group with up to 9 ring atoms, of which 1, 2 or 3 are from the group consisting of nitrogen, oxygen and sulfur, optionally substituted by one or more, identical or different halogen atoms, r6 independently represents the residue of the group G2, or a <

R and R of two directly or indirectly adjacent groups (CR^R^)_ , or (CR^R^)- form together with the carbon atom connecting them an optionally substituted three- to six-membered ring, which optionally contains one or two, identical or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by one or more, identical or different radicals from the group comprising halogen atom, nitro group, cyano group, thiocyanato group and -Β-χ1 group, or

R ⁵ and R ⁶ form with the carbon atom carrying them a carbonyl group, a group CR^^R ¹ ^ or a three- to six-membered ring, which optionally contains one or two identical or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a group -BX ¹ , or r6 represents a heterocyclyl radical,

R denotes a hydrogen atom, an amino group, an alkylcarbonyl, alkylamino or dialkylamino group with 1 to 6 carbon atoms in the alkyl radicals, an acyclic hydrocarbon radical or hydrocarbonoxy radical with 1 to 6 carbon atoms in each case, a cyclic hydrocarbon radical or hydrocarbonoxy radical with 3 to 6 carbon atoms in each case or a heterocyclyl, heterocyclyloxy or heterocyclylamino radical with 3 to 6 ring atoms in each case and with one to three ring heteroatoms from the group comprising nitrogen, oxygen and sulphur, each of the ten latter radicals being optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, an alkoxy group with 1 to 4 carbon atoms, a haloalkoxy group with 1 to 4 carbon atoms, an alkylthio group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, alkynyl group with 2 to 4 carbon atoms, alkenyloxy group with 2 to 4 carbon atoms, alkynyloxy group with 2 to 4 carbon atoms, hydroxy group, amino group, acylamino group, alkylamino group, dialkylamino group, nitro group, carboxy group, cyano group, azido group, 1 to 4 alkoxycarbonyl group by carbon atoms in the alkoxyl,

alkylcarbonyl group with 1 to 4 carbon atoms in the alkyl, formyl group, carbamoyl group, alkylaminocarbonyl and dialkylaminocarbonyl groups with 1 to 4 carbon atoms in the alkyl, alkylsulfinyl group with 1 to 4 carbon atoms, haloalkylsulfinyl group with 1 to 4 carbon atoms, alkylsulfonyl group with 1 to 4 carbon atoms, haloalkylsulfonyl group with 1 to 4 carbon atoms and in the case of cyclic radicals also alkyl group with 1 to 4 carbon atoms and haloalkyl group with 1 to 4 carbon atoms,

O

R denotes an alkyl group with 1 to 10 carbon atoms, an alkenyl group with 2 to 8 carbon atoms, an alkynyl group with 2 to 8 carbon atoms, which are optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a cyano group, a nitro group, a thiocyanato group, a hydroxy group, an alkoxy group with 1 to 4 carbon atoms, an alkylthio group with 1 to 4 carbon atoms, an alkylsulfinyl group with 1 to 4 carbon atoms, an alkylsulfonyl group with 1 to 4 carbon atoms, a phenyl group, a cycloalkyl group with 3 to 9 carbon atoms, a cycloalkoxy group with 3 to 9 carbon atoms and optionally by one or more, identical or different radicals from the group comprising a halogen atom, an amino group, an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, a haloalkyl group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, a substituted heterocyclyl group with three to six ring atoms and with one to three heteroatoms from the group comprising oxygen, nitrogen and sulphur, φ φ φ « · ·· · • · · · · · • φ φ · · · ·· · · φ φ φφ a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkoxy group with 3 to 8 carbon atoms or a heterocyclyl group with 3 to 6 ring atoms, the three latter radicals being optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group, an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, a haloalkyl group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, , rIO independently denotes a hydrogen atom, an amino group, an alkylcarbonyl group with 1 to 10 carbon atoms in the alkyl, an alkylamino group with 1 to 10 carbon atoms, a dialkylamino group with 1 to 10 carbon atoms in each alkyl, an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with up to 8 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, a cycloalkoxy group with 3 to 8 carbon atoms, a heterocyclyl, heterocyclyloxy or heterocyclylamino group with 3 to 6 ring atoms in each case and with 1 to 3 heteroatoms from the group comprising oxygen, nitrogen and sulfur, each of the ten last-mentioned radicals being optionally substituted, or

R^ and r!0 together with the nitrogen atom carrying them form a heterocycle with a total of three to six ring atoms and one to four ring heteroatoms, where in addition to the nitrogen atom present there are optional further ring heteroatoms selected from the group comprising oxygen, nitrogen and sulphur and this heterocycle is optionally substituted, rH denotes a hydrogen atom, an amino group, an alkylamino group with 1 to 10 carbon atoms, a dialkylamino group with 1 to 10 carbon atoms in each alkyl, an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the alkyl, an alkoxy group with 1 to 10 carbon atoms, an alkoxyalkoxy group with 1 to 6 carbon atoms in each alkoxy, a cycloalkoxy group with 3 to 8 carbon atoms, an alkylcarbonyl group with 1 to 10 carbon atoms in the alkyl, the nine latter radicals being optionally substituted,

Ί 9 Ί

R independently represents a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, an alkenyl group with 2 to 8 carbon atoms, an alkynyl group with 2 to 8 carbon atoms, a phenyl group, a phenylalkyl group with 1 to 6 carbon atoms in the alkyl, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the alkyl, the cyclic part of the four latter radicals being optionally substituted by one or more, identical or different radicals from the group comprising an alkyl group with 1 to 4 carbon atoms, a haloalkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, or

R ¹² and R ¹³ together with the group carrying them form N-CO-N

a five- to eight-membered ring which, in addition to the two nitrogen atoms mentioned, may contain another heteroatom from the group comprising oxygen, nitrogen and sulfur and which is optionally substituted,

R-L4 represents a hydrogen atom or an optionally substituted alkyl group or cycloalkyl group with 3 to 10 carbon atoms, , r!6 represents independently of one another a hydrogen atom, an aryl group, an alkoxy group with 1 to 10 carbon atoms, an arylalkyl group with 1 to 6 carbon atoms in the alkyl, an alkyl group with 1 to 10 carbon atoms, an alkylthio group with 1 to 10 carbon atoms, wherein five of the latter radicals are optionally substituted and wherein the aliphatic carbon structure of the three latter radicals may be interrupted by one or more, identical or different, heteroatoms from the group comprising oxygen and sulfur, or

R ¹⁵ and R ¹⁶ form with the carbon atom bearing them a three- to six-membered ring, which optionally contains one or two, the same or different, heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is optionally substituted.

The term aryl group means, for example, phenyl, naphthyl, biphenyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl, aziridinyl, azetidinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, thiazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyridazines• ·

, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, oxazinyl, thiazinyl, thiadiazinyl, dithiazinyl, thioxazinyl, indolyl, benzoxyzyl, benzothiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, purinyl and naphthyridinyl groups. In the case of these aryl residues, the connection with another part of the molecule of the compound of general formula I can take place essentially, that is, if the structure of the ring system allows it, at each position of the aryl residue.

In the case where -Y- or -B- denotes an unsymmetrical divalent unit, i.e. it allows two connection options, the general formula I should always include both connection options of -Y- or -B- and the rest of the molecule.

In formula I and in all the following formulas, the hydrocarbon-containing radicals such as alkyl, alkoxy, haloalkyl, haloalkoxy and alkylamino groups and alkylthio groups, as well as the corresponding unsaturated and/or substituted radicals in the carbon lattice, such as alkenyl or alkynyl groups, can be straight or branched. Unless specifically stated, radicals with a lower number of carbon atoms in the lattice are preferred for these groups, for example up to 6 carbon atoms, or for unsaturated groups up to 4 carbon atoms. Alkyl radicals, also in related meanings such as alkoxy or haloalkyl radicals and the like, denote, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group or a 2-butyl group, pentyl groups, hexyl groups such as the n-hexyl group, the isohexyl group and the 1,3-dimethylbutyl group and heptyl groups such as the n-heptyl group, the 1-methylhexyl group and the 1,4-dimethylpentyl group; alkenyl and alkynyl groups have the meaning of the alkyl groups of the corresponding possible unsaturated radicals; alkenyl denotes, for example, allyl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methyl-but-3-en-1-yl and 1-methyl-but-2-en-1-yl; alkynyl denotes, for example, the pyroxylin group, but-2-yn-1-yl, but-3-yn-1-yl and 1-methyl-but-3-yn-1-yl. The multiple bond may be located at any position of the unsaturated radical.

Cycloalkyl refers to a carbocyclic, saturated ring system with 3 to 9 carbon atoms, for example a cyclopropyl group, a cyclopentyl group or a cyclohexyl group. In the case of compound radicals, such as a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and 1 to 6 carbon atoms in the alkyl, the former radical can be located in any position on the latter radical.

In the case of a doubly substituted amino group, such as a dialkylamino group, both substituents may be the same or different.

Halogen denotes, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, haloalkenyl and haloalkynyl groups denote, for example, a halogen, preferably fluorine, chlorine and/or bromine, in particular fluorine or chlorine, partially or fully substituted alkyl, alkenyl or alkynyl group, for example a monohaloalkyl group or a perhaloalkyl group such as -CF ₃ , -CHF 2 , -CH2F , -CF ₂ CF ₃ , -CHC1CH ₂ F , -CC1 ₃ , -CHC1 ₂ , -CH ₂ CH ₂ C1 ; haloalkoxy groups are, for example, -OCF ₃ , -OCHF2 , -OCH2F , • · · '

-OCF2CF3 , -OCH2CF3 and -OCH2CH2Cl. The same applies to haloalkenyl groups and other halogen-substituted radicals.

An acyl radical denotes an organic acid radical, for example a carboxylic acid radical and radicals derived therefrom, such as thiocarboxylic acids, optionally N-substituted iminocarboxylic acids, or radicals of monoesters of carbonic acid, optionally N-substituted carbamic acid, sulfonic acids, sulfinic acids, phosphonic acids and phosphinic acids. An acyl radical denotes, for example, a formyl radical, an alkylcarbonyl radical, such as an alkylcarbonyl radical with 1 to 4 carbon atoms in the alkyl, a phenylcarbonyl radical, the phenyl ring being optionally substituted, for example as mentioned above for a phenyl radical, an alkoxycarbonyl radical, a phenyloxycarbonyl radical, a benzyloxycarbonyl radical, an alkylsulfonyl radical, an alkylsulfinyl radical, an N-alkyl-1-iminoalkyl radical and other organic acid radicals.

The hydrocarbon radical is a straight, branched or cyclic and saturated or unsaturated, aliphatic or aromatic hydrocarbon radical, for example an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl and fluorenyl group.

Substituted radicals, such as substituted hydrocarbon radicals, for example substituted alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, or substituted heterocyclyl radicals, mean, for example, substituted • ·

residues derived from an unsubstituted basic skeleton, the substituents comprising one or more, preferably unless otherwise stated, 1, 2 or 3 identical or different residues from the group comprising a halogen atom, an alkoxy group, a haloalkoxy group, an alkylthio group, a hydroxy group, an amino group, a nitro group, a carboxy group, a cyano group, an azido group, an alkoxycarbonyl group, a formyl group, a carbamoyl group, an alkylaminocarbonyl and a dialkylaminocarbonyl group, a substituted amino group, such as an acylamino group, an alkylamino group and a dialkylamino group, an alkylsulfinyl group, a haloalkylsulfinyl group, an alkylsulfonyl group, a haloalkylsulfonyl group and in the case of cyclic residues also an alkyl and haloalkyl group, as well as unsaturated aliphatic residues corresponding to the above saturated hydrocarbon-containing residues, such as an alkenyl, alkynyl, alkenyloxy and alkynyloxy group and etc. In the case of carbon radicals, radicals with 1 to 4 carbon atoms are preferred. In this case, substituents from the group comprising halogens, for example fluorine and chlorine, alkyl groups with 1 to 4 carbon atoms, in particular methyl and ethyl groups, haloalkyl groups with 1 to 4 carbon atoms, in particular trifluoromethyl groups, alkoxy groups with 1 to 4 carbon atoms, in particular methoxy or ethoxy groups, haloalkoxy groups with 1 to 4 carbon atoms, nitro groups and cyano groups are generally preferred. Methyl groups, methoxy groups and chlorine atoms are particularly preferred as substituents.

When the hydrocarbon chain of an alkyl, alkenyl or alkynyl radical is interrupted by multiple heteroatoms, they should not be directly adjacent.

• · · ·

The term heterocycle means, unless otherwise stated, 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, cinnoline, thiophene, thiazole, oxazole, oxetane, furan, pyrrole, pyrazole, imidazole, aziridine, oxirane, pyrrolidine, piperidine, piperazine, dioxolane, morpholine and tetrahydrofuran. In this sense, the terms heterocyclyl group and heterocyclic radical should also be understood, i.e. as a radical derived from the above-mentioned heterocycles. If the heterocycle contains at least two heteroatoms, the condition should apply that two oxygen atoms are not directly adjacent. In these heterocycles, the connection to another part of the molecule of the compound of the general formula I can be essential, that is, if the structure of the ring system allows it, it is at every position of the heterocycles. The heterocycle can, unless otherwise stated, be unsubstituted or substituted by one or more, identical or different, radicals. These radicals can be the radicals considered for substituted hydrocarbon radicals and additionally also an oxo group. The oxo group can also occur on heteroatoms of the ring, which can exist in different oxidation states, for example at nitrogen and sulfur.

The ring can be saturated, partially unsaturated, completely unsaturated, or aromatic.

The above examples of residues or residue regions that fall under the general terms alkyl, acyl, substituted residues and the like are not exhaustive. The general terms also include the following definitions of residue regions in the groups of preferred compounds, especially residue regions that include specific residues from the tabular examples.

The compounds of the general formula I can always occur as stereoisomers depending on the type and attachment of the substituents. For example, if one or more alkenyl groups are present, diastereomers can occur. If one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur. Stereoisomers can be obtained from the mixtures obtained during production by means of customary separation methods, for example chromatographic separation procedures. Stereoisomers can also be selectively prepared by using stereoselective reactions using optically active starting materials and/or auxiliaries. The invention also relates to all stereoisomers and mixtures thereof which are included under the general formula I but are not specifically defined.

Compounds of general formula I also include tautomers of compounds formed by hydrogen rearrangement, such as enols and others, even if they do not formally correspond to general formula I.

Depending on the type of substituents, the compounds of the general formula I can form salts and are included under the term compounds of the general formula I. In the case of substituents with acidic properties, such as COOH and SO^H, the hydrogen atom of the acidic group can be replaced by a cation suitable for agriculture. These salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, preferably sodium and potassium salts or also ammonium salts or salts with organic amines. Similarly, the formation of salts can take place by addition of an acid to basic substituents, such as, for example, an amino group.

Suitable acids for this purpose are strong inorganic and organic acids, such as hydrochloric acid, hydrobromic acid, sulfuric acid or nitric acid. Such salts are also a subject of the present invention.

The combination possibilities of the various substituents of the general formula I should be understood in such a way that the general principles of the construction of chemical compounds are taken into account, that is, that compounds are not formed which are known to those skilled in the art to be chemically unstable or impossible.

Preferred are compounds of general formula I and their salts, in which

Aryl denotes an optionally substituted monocyclic or bicyclic aromatic radical with 5 to 10 ring atoms, of which 1, 2, 3 or 4 may independently be derived from the group comprising oxygen, sulphur and nitrogen, and/or —Y— denotes a divalent unit from the group comprising —O—, —S—, —NR ¹¹ —, —NR ¹² C0NR ¹³ —, —C02 —, —OC0NR ¹⁴ —, —SO—, —S02 —, —S0 ₂ 0— and —SO ₂ NR ¹⁴ —, or also a divalent unit from the group comprising —O-NR ¹¹ —, —NH-NH and —O-CR ^and R ^b -CR ^c R ^d -O- , wherein

R ^a , R ^b , R ^c and R ^d independently represent a hydrogen atom, a methyl or ethyl group, or also a trivalent unit of the formula -O-N= , and/or • · · ·

R ² and R ² each independently represent a residue of the group G3 comprising a hydrogen atom, an alkyl group with 1 to carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkoxy group with 3 to 8 carbon atoms, an arylalkyl group with 1 to 6 carbon atoms in the alkyl and a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the alkyl, wherein the cyclic parts of the four latter-mentioned residues are optionally substituted by one or more, identical or different residues from the group comprising a halogen atom, a nitro group, a cyano group and a -BX group, wherein -B- and X are defined below and wherein the non-cyclic parts of the eight latter-mentioned residues of the group G3 are optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a group -BX , wherein -B and X are defined below and wherein the non-cyclic parts of the radicals of the group G3 may be interrupted by one or more, identical or different heteroatoms from the group comprising an oxygen atom and a sulfur atom, or also two R ¹ of two directly adjacent groups (CR R ) together with the bond between the carbon atoms of the groups denote a double bond or two R and two R 1 2 of two directly adjacent groups (CR R ) together with the bond between the carbon atoms of the groups denote a triple bond, or also

Rl denotes the binding site for the double bond in the case where 12

Y denotes a trivalent unit =N-0- adjacent to the CR R group, and/or

R ³ , R ⁴ each independently denotes a residue of the group G4, comprising a hydrogen atom, an alkyl group with 1 to carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkoxy group with 3 to 8 carbon atoms, an aryl group, an arylalkyl group with 1 to 6 carbon atoms in the alkyl, an arylalkoxy group with 1 to 6 carbon atoms in the alkoxyl, a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the alkyl, a cycloalkylalkoxy group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the alkoxyl, a cycloalkoxyalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the alkoxyl, carbon atoms in cycloalkoxy and with 1 to 6 carbon atoms in alkyl and a cycloalkoxyalkoxy group with 3 to 8 carbon atoms in cycloalkoxy and with 1 to 6 carbon atoms in alkoxy, wherein the cyclic part of the nine latter-mentioned residues is optionally substituted by one or more, the same or different residues from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a -BX^ group, wherein -B- and are defined below and wherein the non-cyclic part of the thirteen latter-mentioned residues of the G4 group is optionally substituted by one or more, the same or different residues from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a -BX group, wherein X is defined below and wherein the non-cyclic part of the residues of the G4 group may be interrupted by one or two, the same or different heteroatoms from the group comprising oxygen and sulfur, or also two R ¹ of two directly adjacent groups (CRlR^) together with the bond between the carbon atoms of the groups form a double bond, or also

O O Á two of two directly adjacent groups (CR^R^) together with the bond between the carbon atoms of the groups denotes a double bond or two R^ and two R^ of two directly adjacent groups (CR^R^) together with the bond between the carbon atoms of the groups denotes a triple bond, or also o

R ^J denotes a binding site for a double bond in the case where Y denotes a trivalent unit -O-N= adjacent to the CR^R^ group, and/or

-B- denotes a direct bond or a divalent unit from the group consisting of -O-, -S-, -NrH-, -CO-, -CO2-, -OCO2-, -S0-, -S0 ₂ -, -S0 ₂ 0- and -SO2NR' ¹ ' ⁴ - , and/or χΐ denotes a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms or a heterocyclyl group with 3 to 6 ring atoms, of which 1, 2 or 3 come from the group consisting of a nitrogen, oxygen and sulfur atom and wherein the five latter radicals are optionally substituted by one or more, identical or different, halogen atoms, and/or

X represents a hydrogen atom or a heterocyclyl group with up to 9 ring atoms, of which 1, 2 or 3 are from the group consisting of nitrogen, oxygen and sulfur, or > · · ' ► · · <

• · < • · · · substituted by 1, 2 or 3 identical or different halogen atoms, and/or r5,r6 independently of each other denote the residue of the group G4 , and/or

R? denotes a hydrogen atom, an amino group, an alkylcarbonyl, alkylamino or dialkylamino group with up to 4 carbon atoms in the alkyl radicals, an acyclic or cyclic hydrocarbon radical with 1 to 6 carbon atoms in each case or a heterocyclyl radical with 3 to 6 ring atoms and with one to three ring heteroatoms from the group comprising nitrogen, oxygen and sulphur, each of the six latter radicals being optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, an alkoxy group with 1 to 4 carbon atoms, a haloalkoxy group with 1 to 4 carbon atoms, an alkylthio group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with up to 4 carbon atoms, an alkenyloxy group with 2 to 4 carbon atoms, an alkynyloxy group with 2 to 4 carbon atoms, hydroxy group, amino group, alkylamino group, dialkylamino group, nitro group, carboxy group, cyano group, alkoxycarbonyl group with 1 to 4 carbon atoms in alkoxy, alkylcarbonyl group with 1 to 4 carbon atoms in alkyl, formyl group, carbamoyl group, alkylaminocarbonyl and dialkylaminocarbonyl groups with 1 to 4 carbon atoms in alkyl, alkylsulfonyl group with 1 to 4 carbon atoms, haloalkylsulfonyl group with 1 to 4 carbon atoms and in the case of cyclic radicals also alkyl group with 1 to 4 carbon atoms and haloalkyl group • · • ·

with 1 to 4 carbon atoms, and/or r8 denotes an alkyl group with 1 to 6 carbon atoms, which is optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a cyano group, a nitro group, a thiocyanato group, a hydroxy group, an alkoxy group with 1 to 4 carbon atoms, an alkylthio group with 1 to 4 carbon atoms, an alkylsulfonyl group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, a phenyl group, a cycloalkyl group with up to 9 carbon atoms, a cycloalkoxy group with 3 to 9 carbon atoms and optionally one or more, identical or different radicals from the group comprising a halogen atom, an amino group, an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms atoms, a haloalkyl group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, a substituted heterocyclyl group with three to six ring atoms and with one to three ring heteroatoms from the group comprising oxygen, nitrogen and sulphur, a cycloalkyl group with 3 to 8 carbon atoms or a cycloalkoxy group with 3 to 8 carbon atoms, the latter two radicals being optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, an alkyl group with up to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, a haloalkyl group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, and/or • »

R' independently represents a hydrogen atom, an amino group, an alkylcarbonyl group with 1 to 6 carbon atoms in the alkyl, an alkylamino group with 1 to 6 carbon atoms, a dialkylamino group with 1 to 6 carbon atoms in each alkyl, an alkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cycloalkoxy group with 3 to 6 carbon atoms or a heterocyclyl group with 3 to 6 ring atoms and with 1 to 3 ring heteroatoms from the group comprising oxygen, nitrogen and sulphur, each of the eight latter radicals being optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, an amino group, a hydroxy group and in the case of cyclic radicals also an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, haloalkyl1 to 4 carbon atoms and halogen1 to 4 carbon atoms, and/or the alkoxy group s denotes a hydrogen atom, an amino group, an alkylamino group with 1 to 6 carbon atoms, a dialkylamino group with 1 to 6 carbon atoms in each alkyl, an alkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the alkyl, an alkoxy group with 1 to 6 carbon atoms, an alkoxyalkoxy group with 1 to 6 carbon atoms in each alkoxy, a cycloalkoxy group with 3 to 8 carbon atoms and an alkylcarbonyl group with 1 to 6 carbon atoms in the alkyl, the nine latter radicals being optionally substituted by one or more, the same • ·

or various radicals from the group consisting of a halogen atom, an amino group, a hydroxyl group and, in the case of cyclic radicals, also an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, a haloalkyl group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, and/or

R , R ^±J independently represent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a phenyl group, a phenylalkyl group with 1 to 6 carbon atoms in the alkyl, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the alkyl, the cyclic part of the four latter radicals being optionally substituted by one or more, identical or different radicals from the group comprising an alkyl group with 1 to 4 carbon atoms, a haloalkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, or

11

R and R together with the N-CO-N group carrying them form a five- to eight-membered ring, which in addition to the two nitrogen atoms mentioned may contain another heteroatom from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by one or more, identical or different, radicals from the group comprising a halogen atom, an alkyl group with 1 to 4 carbon atoms and a haloalkyl group with 1 to 4 carbon atoms, • · • ·

- 28 R ²⁴ denotes a hydrogen atom or optionally one or more, identical or different, radicals from the group comprising a halogen atom, a phenyl group, a hydroxy group, an alkoxy group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, an alkyl group with 1 to 6 carbon atoms or a cycloalkyl group with 3 to 8 carbon atoms, and/or

R ²³ , R ² ^ independently represent a hydrogen atom, a phenyl group, an alkoxy group with 1 to 6 carbon atoms, a phenylalkyl group with 1 to 6 carbon atoms in the alkyl, an alkyl group with 1 to 6 carbon atoms and an alkylthio group with 1 to 6 carbon atoms, the five latter radicals being optionally substituted and the aliphatic carbon structure of the three latter radicals being interrupted by one or more, identical or different, heteroatoms from the group comprising oxygen and sulfur.

Also preferred are compounds of general formula I and their salts, in which

Ί 9 . i 9 _v

R and R^ groups (CR ^X R ) form with the carbon atom bearing them a carbonyl group, a CR ²³ R ² ^ group or a three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by one or more, the same or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX ² group,

or

19 two R ¹ of two directly or indirectly adjacent groups (CR R ) form together with the carbon atoms carrying them, optionally connecting them, an optionally substituted three- to six-membered ring, which optionally contains one or two identical or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX^ group.

Also preferred are compounds of general formula I, in which

R ³ and R ⁴ form with the carbon atom carrying them a carbonyl group, a CR^ ³ R^^ group or a three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group comprising oxygen, nitrogen and sulfur and which is optionally substituted by one or more, the same or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX^ group, or two R ³ of two directly or indirectly adjacent groups (CR ³ R ⁴ ) together with the carrying them, optionally connecting carbon atoms, form an optionally substituted three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group comprising oxygen, nitrogen and sulfur and which is optionally substituted by one or more, the same or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX^ group.

Furthermore, compounds of general formula I and their salts are preferred, wherein

R ^a and R ^J of two directly or indirectly adjacent groups (CR ³ R ⁴ ) or (CR ³ R ^) together with the carbon atoms connecting them form an optionally substituted three- to six-membered ring, which optionally contains one or two, identical or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX ¹ group, or

R ³ and R^ with the supporting carbon atom form a carbonyl group

-J r -j zf group, CR ^±J R ^±D group or a three- to six-membered ring which optionally contains one or two, the same or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by one or more, the same or different radicals from the group comprising halogen atom, nitro group, cyano group and -BX ¹ group, or r6 denotes a heterocyclyl group.

Also preferred are compounds of general formula I and their salts, wherein

R ⁹ and R ¹⁰ together with the nitrogen atom carrying them form a heterocycle with a total of three to six ring atoms and one to three ring heteroatoms, with the nitrogen atom present being optionally present.

further ring heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, and this heterocycle is optionally substituted with up to three identical or different radicals, preferably radicals selected from the group consisting of a halogen atom, an amino group, a hydroxy group, an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, a haloalkyl group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms.

Furthermore, compounds of the general formula I and their salts are preferred, wherein a r!6 forms with the carbon atom carrying it a three- to six-membered ring, which optionally contains one or two, identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is optionally substituted by one or more, identical or different radicals from the group consisting of a halogen atom, an alkyl group with 1 to 4 carbon atoms and a haloalkyl group with 1 to 4 carbon atoms.

Particularly preferred are compounds of general formula I and their salts, wherein

Aryl denotes a monocyclic or bicyclic aromatic radical with 5 to 10 ring atoms, of which 1, 2, 3 or 4 may independently be derived from the group comprising oxygen, sulphur and nitrogen, optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a hydroxy group, an amino group, a formyl group, an alkoxycarbonyl group with 1 to 4 carbon atoms in the alkoxyl group, an alkylcarbonyl group with 1 to 4 carbon atoms in the alkyl group, a haloalkoxycarbonyl group with 1 to 4 carbon atoms in the alkoxyl group, a haloalkylcarbonyl group with 1 to 4 carbon atoms in the alkyl group, an alkyl group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, alkoxyalkyl group with 1 to 4 carbon atoms in alkyl and alkoxy, haloalkoxyalkyl group with 1 to 4 carbon atoms in alkyl and alkoxy, haloalkoxy-haloalkyl group with 1 to 4 carbon atoms in alkyl and alkoxy, alkoxy-haloalkyl group with 1 to 4 carbon atoms in alkyl and alkoxy, cycloalkyl group with 3 to 6 carbon atoms, cycloalkylalkyl group with 3 to 6 carbon atoms in cycloalkyl and with 1 to 4 carbon atoms in alkyl, cycloalkyl-haloalkyl group with 3 to 6 carbon atoms in cycloalkyl and with 1 to 4 carbon atoms in alkyl, halocycloalkyl-haloalkyl group with 3 to 6 carbon atoms in cycloalkyl and with 1 to 4 carbon atoms in alkyl, halocycloalkylalkyl group with 3 to 6 carbon atoms in cycloalkyl and with 1 to 4 carbon atoms in alkyl, halocycloalkylalkyl group with 3 to 6 carbon atoms in cycloalkyl and with 1 to 4 carbon atoms in alkyl, alkylamino group and dialkylamino group with 1 to 6 carbon atoms in each alkyl, alkylaminocarbonyl group with 1 to 6 carbon atoms in alkyl, aminosulfonyl group, alkylaminosulfonyl and diallylaminosulfonyl group with 1 to 6 carbon atoms in each alkyl, haloalkyl group with 1 to 4 carbon atoms and haloalkoxy group with 1 to 4 carbon atoms,

-Y- denotes a divalent unit from the group including -O-,

-S-, -NR ¹¹ -, -CO2-, -SO-, -SO2-, -SO20- and -SO2NR ¹⁴ -, or also a unit from the group comprising -NH-CO-NHa -OCONH- or a unit from the group comprising -O-NH-, -O-N= and -O-CH2CH ₂ -O- ,

R ^x and R ⁶ each independently denote a residue of the group G5 , comprising a hydrogen atom, an alkyl group with 1 to carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, a cycloalkoxy group with 3 to 6 carbon atoms, an arylalkyl group with 1 to 6 carbon atoms in the alkyl and a cycloalkylalkyl group with 3 to 6 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the alkyl, wherein the cyclic parts of the four latter-mentioned residues are optionally substituted by one or more, identical or different residues from the group comprising a halogen atom, a nitro group, a cyano group and a -BX ¹ group, wherein -B- and X ¹ are defined below and wherein the non-cyclic parts of the eight latter-mentioned residues of the group G5 are optionally substituted by one or more, identical or different, radicals from the group comprising a halogen atom, a nitro group, a cyano group and a group -BX , wherein -B and X are defined below and wherein the non-cyclic parts of the radicals of the group G5 may be interrupted by one or more, identical or different heteroatoms from the group comprising an oxygen atom and a sulfur atom, or also

12 two R of two directly adjacent groups (CR R ) together with the bond between the carbon atoms of the groups denotes a double bond or two R and two R of two directly adjacent • · • ·

- 34 groups (CR ^d R ² ) together with the bond between the carbon atoms of the groups indicate a triple bond, or

R ¹ denotes the binding site for a double bond in the case where Y denotes a trivalent unit =N-0- adjacent to the CR R group,

R ³ , R ⁴ each independently denotes a residue of the group G6, comprising a hydrogen atom, an alkyl group with 1 to carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkoxy group with 3 to 8 carbon atoms, an aryl group, an arylalkyl group with 1 to 4 carbon atoms in the alkyl, an arylalkoxy group with 1 to 4 carbon atoms in the alkoxy, a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 4 carbon atoms in the alkyl, a cycloalkylalkoxy group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 4 carbon atoms in the alkoxy, a cycloalkoxyalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 4 carbon atoms in the alkoxy, carbon atoms in cycloalkoxy and with 1 to 4 carbon atoms in alkyl and a cycloalkoxyalkoxy group with 3 to 8 carbon atoms in cycloalkoxy and with 1 to 4 carbon atoms in alkoxy, wherein the cyclic part of the nine latter-mentioned residues is optionally substituted by one or more, the same or different residues from the group comprising a halogen atom, a nitro group, a cyano group and a -BX group, wherein -B- and X are defined below and wherein the non-cyclic part of the thirteen latter-mentioned residues of the G6 group is optionally substituted by one or more, the same or different residues from the group comprising a halogen atom, a nitro group, a cyano group and a -BX group, wherein X is defined below and wherein the non-cyclic part of the residues of the G6 group may be interrupted by one heteroatom from the group comprising oxygen and sulfur, or also two R ^J of two directly adjacent groups (CR R ) together with the bond between the carbon atoms form atoms of the groups a double bond, or two R^ and two R ⁴ of two directly adjacent groups (CR^R ⁴ ) together with the bond between the carbon atoms of the groups a triple bond, or also a

R denotes the binding site for the double bond in the case that

Y denotes a trivalent unit -O-N= adjacent to the CR^R ⁴ group,

-B denotes a direct bond or a ny including -0-, -S-, -S0 ₂ -, -so ₂ o- and -SO ₂ NR ¹⁴ divalent unit -NR ^{9 * 11 *} -, -C0-, -C0 ₂ from the group, -S0-,

X ¹ represents a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms or a heterocyclyl group with 3 to 6 ring atoms, of which 1, 2 or 3 are derived from the group consisting of a nitrogen, oxygen and sulfur atom and wherein the five latter radicals are optionally substituted by up to five identical or different halogen atoms,

X represents a hydrogen atom or a heterocyclyl group with up to 6 ring atoms, of which 1, 2 or 3 are from the group consisting of nitrogen, oxygen and sulfur, optionally

- 36 substituted by 1, 2 or 3 identical or different halogen atoms, r5,r6 independently of each other denote the residue of the group G6,

R denotes a hydrogen atom, an amino group, an alkylcarbonyl, alkylamino or dialkylamino group with 1 to 4 carbon atoms in each alkyl radical or an acyclic or cyclic hydrocarbon radical with 1 to 6 carbon atoms, each of the five latter radicals being optionally substituted by one or more identical or different radicals from the group comprising a halogen atom, an alkoxy group with 1 to 4 carbon atoms, a haloalkoxy group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, an alkenyloxy group with 2 to 4 carbon atoms, an alkynyloxy group with 2 to 4 carbon atoms, a hydroxy group, an amino group, an alkylamino and dialkylamino group with 1 to 4 carbon atoms in each alkyl radical, a nitro group, a carboxy group, cyano group, alkoxycarbonyl group with 1 to 4 carbon atoms in alkoxy, alkylcarbonyl group with 1 to 4 carbon atoms in alkyl, formyl group, carbamoyl group, alkylsulfonyl group with 1 to 4 carbon atoms and haloalkylsulfonyl group with 1 to 4 carbon atoms and in the case of cyclic radicals also alkyl group with 1 to 4 carbon atoms and haloalkyl group with 1 to 4 carbon atoms,

O

R denotes an alkyl group with 1 to 6 carbon atoms, which is optionally substituted by one or more, • · identical or different radicals from the group comprising a halogen atom, a cyano group, a hydroxy group, an alkoxy group with 1 to 4 carbon atoms, an alkylthio group with 1 to 4 carbon atoms, an alkylsulfonyl group with 1 to 4 carbon atoms, an alkenyl group with up to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, a phenyl group, a cycloalkyl group with 3 to 9 carbon atoms and a cycloalkoxy group with 3 to 9 carbon atoms and further denotes a cycloalkyl group with 3 to 8 carbon atoms or a cycloalkoxy group with 3 to 8 carbon atoms, the latter two radicals being optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, an alkyl group with up to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, a haloalkyl group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, , R1® independently denotes a hydrogen atom, an amino group, an alkylcarbonyl group with 1 to 4 carbon atoms in the alkyl, an alkylamino group with 1 to 4 carbon atoms, a dialkylamino group with 1 to 4 carbon atoms in each alkyl, an alkyl group with 1 to 4 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, a cycloalkoxy group with 3 to 8 carbon atoms or a heterocyclyl group with up to 6 ring atoms and with 1 to 3 heteroatoms in the ring from the group consisting of oxygen, nitrogen and sulfur, each of the eight latter radicals being optionally substituted with one to four, the same or different • ·

radicals from the group comprising a halogen atom, an amino group, a hydroxyl group and, in the case of cyclic radicals, also an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, a haloalkyl group with up to 4 carbon atoms and a halo group with an alkoxy group with up to 4 carbon atoms,

R ²² denotes a hydrogen atom, an amino group, an alkylamino group with 1 to 4 carbon atoms, a dialkylamino group with 1 to 4 carbon atoms in each alkyl, an alkyl group with 1 to 4 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 4 carbon atoms in the alkyl, an alkoxy group with 1 to 4 carbon atoms, an alkoxyalkoxy group with 1 to 4 carbon atoms in each alkoxy, a cycloalkoxy group with 3 to 8 carbon atoms and an alkylcarbonyl group with 1 to 4 carbon atoms in the alkyl, the nine latter radicals being optionally substituted by one or more identical or different halogen atoms and, in the case of cyclic radicals, also by an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, haloalkyl group with 1 to 4 carbon atoms and haloalkoxy group with 1 to 4 carbon atoms, denotes a hydrogen atom or optionally one or more, identical or different radicals from the group comprising a halogen atom, an alkoxy group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms substituted with an alkyl group with 1 to 4 carbon atoms or a cycloalkyl group with 3 to 6 carbon atoms, and/or • · · φ • φ · · φ * φ · φ φ · φ r!6 denotes independently of one another a hydrogen atom, a phenyl group, an alkoxy group with 1 to 4 carbon atoms, a phenylalkyl group with 1 to 4 carbon atoms in the alkyl, an alkyl group with 1 to 4 carbon atoms and an alkylthio group with 1 to 4 carbon atoms, the five latter radicals being optionally 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 comprising a halogen atom, an alkyl group with 1 to 4 carbon atoms and a haloalkyl group with 1 to 4 carbon atoms.

Compounds of the general formula I according to the present invention which contain only one or more of the abovementioned preferred radicals are also preferred.

Also particularly preferred are compounds of the general formula I, in which

19

The R ^x and R groups (CR^R^) form, with the carbon atom carrying them, a carbonyl group, a CR ³ R group or a three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by up to four identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX^ group, or two R l of two directly or indirectly adjacent groups (CR R ) form, together with the carbon atoms carrying them, optionally connecting them, an optionally substituted three- to six-membered ring, which optionally contains one or two identical or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by up to four identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX ⁴ group.

Also particularly preferred are compounds of the general formula I, in which

R ³ and R ⁴ form with the carbon atom carrying them a carbonyl group, a group CR^ ³ R ⁴ ^ or a three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group comprising oxygen, nitrogen and sulfur and which is optionally substituted by up to four identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX^ group, or two R ³ of two directly or indirectly adjacent groups (CR ³ R ⁴ ) together with the carrying them, optionally connecting carbon atoms, form an optionally substituted three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group comprising oxygen, nitrogen and sulfur and which is optionally substituted by up to four identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX^ group.

Furthermore, compounds of the general formula I and their salts are preferred, wherein • « and R^ of two directly or indirectly adjacent groups (CR^R^) or (CR^R^) together with the carbon atoms connecting them form an optionally substituted three- to six-membered ring, which optionally contains one or two, identical or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by up to four identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -B-X^ group, or

R and R° with the supporting carbon atom form a carbonyl

-tc J Λ group, CR ^1J R ^TU group or a three- to six-membered ring which optionally contains one or two, the same or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by one or more, the same or different radicals from the group comprising halogen atom, nitro group, cyano group, thiocyanato group and -BX^ group, or r6 denotes a heterocyclyl group.

Also particularly preferred are compounds of the general formula I, wherein

R^ and R^O together with the nitrogen atom carrying them form a heterocycle with a total of three to six ring atoms and one to four ring heteroatoms, where in addition to the nitrogen atom present, there are optionally further ring heteroatoms selected from the group comprising oxygen, nitrogen and sulfur, and this heterocycle is optionally substituted.

• · in w · · · • · · · ·* • · ·

In addition, compounds of the general formula I are particularly preferred, wherein

R ¹³ and R ¹ ^ form with the carbon atom carrying it a three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is optionally substituted with up to four, the same or different radicals from the group consisting of a halogen atom, an alkyl group with 1 to 4 carbon atoms and a haloalkyl group with 1 to 4 carbon atoms.

Very particularly preferred are compounds of the general formula I, wherein

Aryl denotes a phenyl, naphthyl, pyridinyl, pyrimidinyl, furanyl, benzofuranyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, oxadiazolyl or thienyl group, which are optionally substituted by one or more, identical or different, radicals from the group comprising a halogen atom, a hydroxy group, an amino group, a formyl group, an alkoxycarbonyl group with 1 to 4 carbon atoms in the alkoxy, an alkylcarbonyl group with 1 to 4 carbon atoms in the alkyl, an alkyl group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, an alkylamino group and a dialkylamino group with 1 to 4 carbon atoms in each alkyl, an aminocarbonyl group, an alkylaminocarbonyl group and a dialkylaminocarbonyl group with 1 to 4 carbon atoms in each alkyl, an aminosulfonyl group, an alkylaminosulfonyl group and a diallylaminosulfonyl group each with 1 to 4 carbon atoms in each alkyl, a haloalkyl group with 1 to 4 carbon atoms, a haloalkoxy group with 1 to 4 carbon atoms, an alkylthio group with 1 to 2 carbon atoms, an alkylsulfinyl group with 1 to 2 carbon atoms, an alkylsulfonyl group with 1 to 2 carbon atoms, a haloalkylthio group with up to 2 carbon atoms, a haloalkylsulfinyl group with 1 to 2 carbon atoms and a haloalkylsulfonyl group with 1 to 2 carbon atoms, —Y— denotes a divalent unit from the group comprising —O—,

-S-, -NrH-, -C0 ₂ - , -S0- and -S0 ₂ ~, or also a divalent unit from the group comprising -NH-CO-NHa -OCONH- or also a unit from the group comprising -O-NH-, -O-N= and -O-CH ₂ CH ₂ -O- , m denotes an integer from 0 to 5, preferably 0, 1, 2 or 3, in particular 0 or 1, n denotes an integer from 1 to 5, preferably 1, 2, 3 or 4, in particular 1, 2 or 3,

2

R and R each independently denote a residue of the group G7, comprising an alkyl group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, a hydrogen atom or a cycloalkyl group with 3 to 6 carbon atoms, the latter residue being optionally substituted by up to four identical or different residues from the group comprising a halogen atom and a -Βχΐ group and the four first-mentioned residues of the group G7 being optionally substituted by one or

more, identical or different radicals from the group comprising a halogen atom and a group -BX, wherein -B and X are defined below, or also

-i 9

R and R form a carbonyl group with the carbon atom bearing them, or

R ⁴ denotes the binding site for a double bond in the case where Y denotes a trivalent unit =N-0- adjacent to the CR R group,

R ³ , R ⁴ each independently denotes a residue of the group G8, comprising a hydrogen atom, an alkyl group with 1 to carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, a cycloalkoxy group with 3 to 6 carbon atoms, an aryl group, an arylalkyl group with 1 to 2 carbon atoms in the alkyl, an arylalkoxy group with 1 to 2 carbon atoms in the alkoxyl, a cycloalkylalkyl group with 3 to 6 carbon atoms in the cycloalkyl and with 1 to 2 carbon atoms in the alkyl, a cycloalkoxyalkylol group with 3 to 8 carbon atoms in the cycloalkoxyl and with 1 to 4 carbon atoms in the alkyl, the cyclic part of the seven last-mentioned residues being optionally substituted with up to four identical or different radicals from the group consisting of a halogen atom, a nitro group, a cyano group and a -BX ⁴ group, wherein -Ba X ⁴ are defined below and wherein the non-cyclic part of the eleven latter-named radicals of the group G8 is optionally substituted with one or more identical or different radicals from the group consisting of a halogen atom, a nitro group, a cyano group and a -BX 4 group, wherein X is defined below, or also

2 A two of two directly adjacent groups (CR R ) together with the bond between the carbon atoms of the groups form a double bond, or two R^ and two R^ of two directly adjacent groups (CR ² R^) together with the bond between the carbon atoms of the groups form a triple bond, or

R ² and R 3 form a carbonyl group with the carbon atom bearing them, or

R denotes the binding site for the double bond in the case where

Y denotes a trivalent unit -O-N= adjacent to the CR ² R^ group,

-B- denotes a direct bond or a divalent unit from the group consisting of -O-, -S-, -NR^^-, -CO- and -CO2-, χΐ denotes a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms or a cycloalkyl group with 3 to 6 carbon atoms, the four latter radicals being optionally substituted by up to five identical or different halogen atoms,

X represents a hydrogen atom or a heterocyclyl group with up to 6 ring atoms, of which 1, 2 or 3 are from the group consisting of nitrogen, oxygen and sulfur, optionally substituted by one or more identical or different halogen atoms,

R ³ represents a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, a haloalkyl group with 1 to 4 carbon atoms or a cycloalkyl group with 3 to 6 carbon atoms, r 6 represents a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, a cycloalkylalkyl group with 3 to 6 carbon atoms in the cycloalkyl and with 1 to 4 carbon atoms in the alkyl, a cycloalkoxyalkyl group with 3 to 6 carbon atoms, an alkoxyalkyl group with 1 to 4 carbon atoms in the alkyl and an alkoxyl or haloalkyl group with 1 to 4 carbon atoms,

Π

R represents a hydrogen atom, an amino group or an alkyl group with 1 to 4 carbon atoms,

R represents an alkyl group with 1 to 4 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, a halocycloalkyl group with 3 to 6 carbon atoms or a cycloalkylalkyl group with 3 to 6 carbon atoms in the cycloalkyl and 1 to 4 carbon atoms in the alkyl,

R^, rIO independently represent a hydrogen atom, an amino group, a formyl group or an alkyl group with 1 to 4 carbon atoms, • ·

R ¹¹ represents a hydrogen atom, an amino group, an alkylamino group with 1 to 4 carbon atoms, a dialkylamino group with 1 to 4 carbon atoms in each alkyl, an alkyl group with 1 to 4 carbon atoms or a cycloalkyl group with 3 to 6 carbon atoms, the five latter radicals being optionally substituted by one or more identical or different halogen atoms and/or

R ^3-4 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

Compounds of the general formula I according to the present invention which contain only one or more of the particularly preferred radicals mentioned are also particularly preferred.

Compounds of the general formula I in which two R^ are directly or indirectly

Ί O of adjacent groups (CR R ) together with the carbon atoms carrying or connecting them form a three-, five- or six-membered ring, which optionally contains up to two heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by up to four identical or different radicals from the group comprising a halogen atom and a group -B-X^·.

Also very particularly preferred are compounds of the general formula I in which two R° of two directly or indirectly adjacent groups (CR R ) together with the carbon atoms carrying them or connecting them form an optionally substituted three-, five- or six-membered ring, which may optionally contain up to two heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is optionally substituted by up to four identical or different radicals from the group consisting of a halogen atom and a group -BX ¹ .

Furthermore, compounds of the general formula I are particularly preferred, wherein

5

R and R of two directly or indirectly adjacent groups (CR ³ R ⁴ ) or (CR^R^) together with the carbon atoms connecting them optionally form up to four identical or different radicals from the group comprising a halogen atom and the group -BX ¹ a substituted three-membered, five-membered or six-membered ring, which optionally contains up to two heteroatoms from the group comprising oxygen, nitrogen and sulphur.

Compounds of the general formula I are also particularly preferred, wherein

R^ and R ¹ ® together with the nitrogen atom carrying them form a heterocycle with a total of three to six ring atoms and one to two ring heteroatoms, with the nitrogen atom present and optionally other ring heteroatoms selected from the group comprising oxygen and nitrogen.

The present invention also provides a process for the production of compounds of general formula I or their salts, the essence of which consists in

a) react the compound of general formula II • ·

R ⁸ - Fu (II), in which

Fu denotes a functional group from the group consisting of carboxylic acid esters, carboxylic acid orthoesters, carboxylic acid chlorides, carboxylic acid amides, carboxylic acid anhydrides and a trichloromethyl group, with a biguanide of general formula III or an acid addition salt thereof

NH

NH

H

or

b) react the compound of general formula IV

(IV) in which

Z ¹ denotes an exchangeable residue or a leaving group, for example a chlorine atom, a trichloromethyl group, an alkylsulfonyl group with 1 to 4 carbon atoms and an unsubstituted or substituted phenylalkylsulfonyl or alkylphenylsulfonyl group with 1 to 4 carbon atoms in the alkyl, with a suitable amine of the general formula V or an acid addition salt thereof

R®

Aryl — (CR ¹ R ² ) —Y — (CR ³ R ⁴ )„ CR ⁵ — NHR ⁷ ( ^v ) wherein in formulas II, III, IV and V the radicals R ¹ to R ¹⁹ and Y have the meanings given in formula I .

The reaction of the compounds of the general formula II and III is preferably carried out under base catalysis in inert organic solvents, such as tetrahydrofuran, dioxane, acetonitrile, dimethylformamide, methyl alcohol and ethyl alcohol, at temperatures in the range of -10 °C and the boiling point of the solvent used, preferably in the range of 20 °C to 60 °C. If acid addition salts of the general formula III are used, these are usually released in situ by means of bases. Suitable bases or basic catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alcoholates, 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 corresponding base is used, for example, in the range of 0.1 to 3 molar equivalents, based on the compound of the general formula III. The compound of the general formula II can be used equimolarly or in an excess of up to 2 molar equivalents relative to the compound of the general formula III.

In principle, corresponding methods are known from the literature (see Comprehensive Heterocyclic Chemistry, A. R. Katritzky, C. V.

Rees, Pergamon Press, Oxford, New York, 1984, Vol. 3; Part 2B; ISBN 0-08-030703-5, p. 290).

The reaction of the compounds of the general formula IV and V is preferably carried out as base-catalyzed in inert organic solvents, such as tetrahydrofuran, dioxane, acetonitrile, dimethylformamide, methyl alcohol and ethyl alcohol, at a temperature in the range of -10 ° C to the boiling point of the corresponding solvent or solvent mixture, preferably in the range of 20 ° C to 60 ° C, wherein the compound of the general formula V, when used as an acid addition salt, is optionally released in situ by means of a base. Suitable bases or basic catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alcoholates, 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 corresponding base is generally used in the range of 1 to 3 molar equivalents, based on the compound of the general formula IV, the compound of the general formula IV can, for example, be used equimolarly to the compound of the general formula V or in an excess of up to 2 molar equivalents. In principle, corresponding methods are known from the literature (see Comprehensive Heterocyclic Chemistry, A. R. Katritzky, C. V. Rees, Pergamon Press, Oxford, New York, 1984, Vol. 3; Part 2B; p. 482).

The starting materials of the formulae II, III, IV and V are either commercially available or can be prepared analogously to methods known from the literature. The compounds can also be prepared, for example, by the process described below.

The compound of general formula IV or its direct precursor can be prepared, for example, in the following manner:

1. By reacting a compound of general formula II with an amidino-thiourea derivative of general formula VI

NH NH r-s-Nfť-U-N

H nr ⁹ r ¹⁰ (VI) in which about

Z represents an alkyl group with 1 to 4 carbon atoms or a phenylalkyl group with 1 to 4 carbon atoms in the alkyl, compounds of the general formula IV are prepared in which Z ¹ = -SZ ² .

2. By reacting an amidine of general formula VII or its addition salt with an acid

R η,νΆ

O in which R has the meaning given in formula I, with N-cyanodithioiminocarbonate of general formula VIII sz ³ (Vlil)

NC—N=r

OT ³ • · in which

Z ³ represents an alkyl group with 1 to 4 carbon atoms or a phenylalkyl group with 1 to 4 carbon atoms in the alkyl, compounds of the general formula IV are obtained in which Z ¹ = -SZ ³ .

3. The reaction of an alkali metal dicyanamide with a carboxylic acid derivative of the above general formula II gives compounds of the general formula IV, in which

Z ¹ = nh ₂ .

4. By reaction of trichloroacetonitrile with a nitrile of general formula IX

R ⁸ - CN (IX) ,

In which R has the meaning given in formula I, compounds of the general formula X are first obtained.

From ⁴

in which Z ¹ and Z ⁴ each represent a trichloromethyl group, • · which, by subsequent reaction with compounds of the general formula HNR^R^O , in which R^ and R^-θ have the meanings as in formula I , lead to compounds of formula IV , in which represents a trichloromethyl group.

The reaction of the carboxylic acid derivatives of the general formula II with the amidinothiourea derivatives of the general formula VI is preferably carried out under base catalysis in organic solvents, such as acetone, tetrahydrofuran, dioxane, acetonitrile, dimethylformamide, methyl alcohol or ethyl alcohol, at a temperature in the range of -10 ° C to the boiling point of the solvent, preferably in the range of 0 ° C to 20 ° C. However, the reaction can also take place in water or in aqueous solvent mixtures with one or more of the above-mentioned organic solvents. If the compound of the general formula VI is used as an acid addition salt, it can also be liberated in situ by means of a base. Suitable bases or basic catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alcoholates, 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 corresponding base is generally used in the range of 1 to 3 molar equivalents, based on the compound of the general formula VI. The compounds of the general formula II and VI can, for example, be used equimolarly or in an excess of up to 2 molar equivalents of the compound of the general formula II. In principle, the corresponding processes are known from the literature (see H. Eilingsfeld, H. Scheuermann, Chem. Ber.; 1967, 100, 1874), the corresponding intermediates of the general formula IV are new.

The reaction of the amidines of the general formula VII with the N-cyanodithioiminocarbonates of the general formula VIII is preferably carried out under base catalysis in organic solvents, such as acetonitrile, dimethylacetamide, N-methylpyrrolidone, methyl alcohol or ethyl alcohol, at a temperature in the range of -10 ° C to the boiling point of the solvent, preferably in the range of 20 ° C to 80 ° C. If the compound of the general formula VII is used as an acid addition salt, it can also be released in situ by means of a base. Suitable bases or basic catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alcoholates, 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 corresponding base is generally used in the range of 1 to 3 molar equivalents, based on the compound of the general formula VIII. The compounds of the general formula VII and VIII can generally be used equimolarly or in excess of up to 2 molar equivalents of the compound of the general formula II. In principle, the corresponding methods are known from the literature (see T. A. Riley, V. J. Henney, N. K. Dalley, Β. E. Vilson, R. K. Robins, J. Heterocyclic Chem.; 1986, 23 (6), 1706-1714), the corresponding intermediates of the general formula IV are new.

The production of intermediates of the general formula X , where Z ¹ = Cl, can be carried out by reacting an alkali metal dicyanamide with a carboxylic acid derivative of the general formula II , wherein Fu then preferably denotes a carboxylic acid chloride or carboxylic acid amide functional group. The reaction of the reaction components takes place, for example, under acid catalysis in inert organic solvents, such as toluene, chlorobenzene or chlorinated hydrocarbons, at a temperature of • ·

in the range of -10 °C to the boiling point of the solvent used, preferably at a temperature in the range of 20 °C to 80 °C, the resulting intermediates can be chlorinated in situ using a suitable chlorinating agent, such as phosphorus oxychloride. Suitable acids include, for example, hydrohalic acids, such as hydrochloric acid, or Lewis acids, such as aluminum chloride or boron trifluoride (see, for example, US-A-5,095,113).

The preparation of intermediates of the general formula X, where Z ¹ , Z ⁴ = trihalomethyl, can be carried out by reacting the corresponding trihaloacetic acid nitriles with the carboxylic acid nitrile of the general formula IX. The reaction of the corresponding reaction components takes place, for example, under acid catalysis in inert organic solvents, such as toluene, chlorobenzene or chlorinated hydrocarbons, at a temperature in the range of -40 ° C to the boiling point of the solvent used, preferably at a temperature in the range of -10 ° C to 30 ° C. Suitable acids include, for example, hydrohalic acids, such as hydrochloric acid, or also Lewis acids, such as aluminum chloride or boron trifluoride (see, for example, EP-A-130 939).

Intermediates of the general formula IV, in which Z ¹ = alkyl mercapto group with 1 to 4 carbon atoms or unsubstituted phenyl-alkyl mercapto group with 1 to 4 carbon atoms in the alkyl, can be converted in inert organic solvents, such as toluene, chlorobenzene, chlorinated hydrocarbons and the like, at a temperature in the range of -40 °C to the boiling point of the solvent used, preferably in the range of 20 °C to 80 °C, using a suitable chlorinating agent, such as elemental chlorine or phosphorus oxychloride, to reactive chlorotriazines of the general formula IV, in which • ·

= chlorine (see J.K. Chakrabarxi, D.E. Tupper; Tetrahedron 1975, 31 (16), 1879-1882).

Intermediates of general formula IV, in which = alkylmercapto group with 1 to 4 carbon atoms, unsubstituted or substituted phenyl-alkylmercapto group with 1 to 4 carbon atoms in alkyl or alkyl-phenylthio group with 1 to 4 carbon atoms in alkyl, can be oxidized in suitable solvents, such as chlorinated hydrocarbons, acetic acid, water, alcohols and acetone or mixtures thereof, at a temperature in the range of 0 °C to the boiling point of the solvent used, preferably in the range of 20 °C to 80 °C, using a suitable oxidizing agent, such as m-chloroperbenzoic acid, hydrogen peroxide or potassium peroxomonosulfate (see T. A. Riley, V. J. Henney, N. K. Dalley,

B. E. Wilson, R. K. Robins; J. Heterocyclic Chem.; 23(6), 1706-1714).

The following acids are suitable for preparing acid addition salts of compounds of the general formula I: hydrohalic acids, such as hydrochloric acid or hydrobromic acid, phosphoric acid, nitric acid, sulfuric acid, monofunctional or bifunctional carboxylic and hydroxycarboxylic acids, such as acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid or lactic acid, as well as sulfonic acids, such as p-toluenesulfonic acid or 1,5-naphthalenedisulfonic acid. The acid addition salts of the general formula I can be obtained in a simple manner using conventional salt formation methods, for example by dissolving the compound of the general formula I in a suitable organic solvent, such as methyl alcohol, acetone, methylene chloride or gasoline and adding the corresponding acid at a temperature in the range of 0 °C to 100 °C and isolated by known methods, for example by filtration and optionally purified by washing with suitable organic solvents.

The addition salts of the compounds of the general formula I with bases are preferably prepared in inert polar solvents, such as water, methanol or acetone, at a temperature in the range of 0° C. to 100° C. Suitable bases for the preparation of the salts according to the present invention are, for example, alkali metal carbonates, such as potassium carbonate, alkali metal and alkaline earth metal hydroxides, for example sodium hydroxide or potassium hydroxide, alkali metal and alkaline earth metal hydrides, for example sodium hydride, alkali metal and alkaline earth metal alcoholates, for example sodium ethoxide or potassium tert-butylate, or ammonia or ethanolamine.

The solvents referred to as inert solvents in the previous variants of the methods are those which are inert under the given reaction conditions, but may not always be inert under any reaction conditions.

The compounds of the present invention of the general formula I have excellent herbicidal activity against a wide range of economically important monocotyledonous and dicotyledonous harmful plants. Even perennial weeds that are difficult to control and that grow from rhizomes, rhizomes or other permanent organs are effectively controlled by the active substance. It is the same whether the substances are applied before sowing, before emergence or after emergence.

It is possible to mention, for example, some representatives of monocotyledonous and dicotyledonous weeds which can be controlled by the compounds according to the present invention, without this mention being intended to imply a restriction to these particular species.

Among monocotyledonous weeds, for example, the species Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and Cyperus from the annual group are well controlled, and among perennial species, the species Agropyron, Cynodon, Imperata and Sorghum, as well as perennial Cyperus species, are well controlled.

In dicotyledonous weeds, the spectrum of action covers species such as Gallium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapsis, Ipomoea, Matricaria, Abutilon and Sida from the annual group, as well as Convolvulus, Cirsium, Rumex and Artemisia from the perennial weeds.

Weeds occurring under specific rice growing conditions, for example Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus, are also excellently controlled by the active ingredients according to the present invention.

When the compounds of the present invention are applied to the soil surface before germination, either the weed seed shoots are completely destroyed or the weeds grow to the cotyledon stage, but then their growth stops and they finally die completely after three to four weeks.

When applying active ingredients to the green parts of plants during the post-emergence phase, a drastic growth stoppage also occurs very quickly after treatment, and the weed plants remain in the growth stage reached at the time of application, or die completely after a certain period of time, so that in this way weed competition, harmful to cultivated plants, is very quickly and thoroughly eliminated.

Although the compounds of the present invention exhibit excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, they do not harm economically important crops such as wheat, barley, rye, rice, corn, sugar beet, cotton and soybeans at all or only to a negligible extent. The compounds are therefore very well suited for the selective treatment of unwanted plant growth in agricultural crops or in the cultivation of ornamental plants.

Due to their herbicidal and growth-regulating properties, the active ingredients can also be used to control harmful plants in crops of known or still being developed genetically modified plants. Transgenic plants are usually characterized by particularly advantageous properties, for example resistance to aphids, to certain pesticides, in particular certain herbicides, resistance to plant diseases or to plant disease agents, such as certain insects or microorganisms, such as fungi, bacteria or viruses.

Other special properties relate to the harvest with regard to quantity, quality, storage life, composition and special constituents. Thus, transgenic plants with increased starch content or altered starch quality, or those with a different fatty acid composition in the harvested material, are known.

It is advantageous to use the compounds of the present invention of the general formula I or their salts in economically important transgenic crops of useful and ornamental plants, for example cereals such as wheat, barley, rye, oats, millet, rice, cassava and maize, or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables. The compounds of the general formula I can be used as herbicides in crops of useful plants which are resistant to the phytotoxic effects of herbicides or which have been rendered resistant by genetic engineering.

Existing methods for producing new plants which have modified properties compared to existing plants consist, for example, of the classical breeding process and the preparation of mutants. Alternatively, new plants with altered properties can be produced using genetic engineering methods (see, for example, EP-A 0 221 044 and EP-A 0 131 624). For example, in many cases, genetic engineering changes of crop plants have been described for the purpose of modifying the starches synthesized in plants (for example, WO 92/11376, WO 92/14827, WO 91/19806), transgenic crop plants that are resistant to certain herbicides of the Glufosinate type (see for example EP-A 0 242 236 and EP-A 0 242 245) or Glyphosate (VO 92/00377) or sulfonylureas (EP-A 0 257 993, US 5 013 659), transgenic crop plants, for example cotton, with the ability to produce Bacillus thuringiensis toxins (Bt-toxins), which make plants resistant to certain pests (EP-A 0 142 924 and EP-A 0 193 259), transgenic crop plants with a modified fatty acid composition. (VO 91/13972).

Various molecular biological techniques by which new transgenic plants with altered properties can be produced 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, NY; or Vinnacker Gene und Klone, VCH Veinheim, 2nd ed., 1996, or Christou, Trends in Plant Science 1(1996) 423-431).

For such genetic engineering manipulations, nucleic acid molecules can be introduced into plasmids, which allow the sequence of the DNA sequence to be changed by recombination. For example, base exchanges, removal of partial sequences or addition of natural or synthetic sequences can be carried out using the standard procedures mentioned above. To connect the DNA fragments to each other, adapters or linkers can be attached to the fragments.

The production of plant cells with reduced gene product activity can be achieved, for example, by expressing at least one corresponding antisense RNA, one sense RNA to achieve a co-suppressive effect, or by expressing at least one correspondingly designed ribozyme that specifically cleaves transcripts of the above-mentioned gene product.

For this purpose, either a DNA molecule that includes the entire coding sequence of the gene product, including any flanking sequences, or DNA molecules that include only parts of the coding sequences, which must be long enough to cause an antisense effect in cells, can be used. It is also possible to use DNA sequences that have a high degree of homology to the coding sequences of the gene product, but are not completely identical.

When expressing nucleic acid molecules in plants, the synthesized protein can be localized in any desired compartment of the plant cell. However, in order to achieve localization in one specific compartment, for example, the coding region can be linked to a DNA sequence that ensures localization in a specific compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Volter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant. J. 1 (1991), 95-106).

Transgenic plant cells can be regenerated into whole plants using known techniques. Transgenic plants can in principle be plants of any species, i.e. both monocotyledonous and dicotyledonous plants.

Thus, transgenic plants can be obtained which have altered properties by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or by expression of heterologous (=foreign) genes or gene sequences.

Advantageously, the compounds of the present invention can be used in transgenic crops that are resistant to herbicides from the group consisting of sulfonylureas, glufosinate-ammonium or glufosinate-isopropylammonium and analogous active ingredients.

When using the active compounds according to the present invention in transgenic crops, in addition to the effects against harmful plants observed in other crops, there are often effects that are specific to the corresponding transgenic crops, such as, for example, a changed or specifically expanded spectrum of weeds that can be controlled, changed application rates that can be used for application, preferably good compatibility with herbicides to which the transgenic crops are resistant, as well as an influence on the growth and yield of the transgenic crop plants.

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

In addition, the substances according to the present invention have significant growth-regulating properties in cultivated plants. They have a regulatory effect on the plant's own metabolism and can therefore be used to specifically influence the content of substances in plants and to facilitate harvesting, for example by inducing desiccation and stopping growth. Furthermore, they are also suitable for the fundamental control and suppression of unwanted vegetative growth without the plants being killed. Suppression of vegetative growth plays a significant role in many monocotyledonous and dicotyledonous crops, since this can reduce or completely prevent storage.

The present invention also provides herbicidal and growth regulating compositions containing compounds of the general formula I. The compounds according to the present invention can be used in the form of conventional preparations known to those skilled in the art, such as wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules.

The compounds of the general formula I can be formulated in various forms, each depending on the biological and/or physicochemical parameters to be determined. Possible formulations include, for example, wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EV), such as water-in-oil and oil-in-water emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), stains, granules for spreading and soil application, granules (GR) in the form of microgranules, spray granules, coated granules and adsorption granules, water-dispersible granules (VG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

These individual types of formulations are known in principle and are described, for example, in the publications Vinnacker-Küchler, Chemische Technologie, Vol. 7, C. Hauser Verlag Munich,

4th ed. 1986; Vade van Valkenburg, Pesticide Formulations, Marcel Dekker, N.Y., 1973; K. Martens, Spray Drying Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.

The necessary auxiliaries for the above formulations, such as inert materials, surfactants, solvents and other additives, are also known and are described, for example, in the publications: Vatkiuns, Handbook of Insecticide Dust Diluent and Carries, 2nd ed., Darland Books, Caldwell N.J.;

H. v. Olphen, Introduction to Clay Colloid Chemistry, 2nd ed., J. Viley & 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. What. lne., N.Y. 1964; Schonfeldt, Grenzfláchenaktive Athylenoxidaddukte, Viss. Verlagsgesellschaft, Stuttgart 1976 ; Vinnacker-Kuchler, Chemische Technologie, Volume 7, C. Hauser Verlag Munich, 4th ed. 1986.

Spray powders are preparations that are uniformly dispersible in water and which, in addition to the active substance, contain, in addition to a diluent or inert substance, surfactants of the ionic and/or non-ionic type (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, polyglycol ether sulfates of fatty alcohols, alkanesulfonates, alkylbenzenesulfonates, sodium salts of lignin acids, sodium salt of 2,2'-dinaphthylmethane-6,6'-disulfonic acid, sodium salt of dibutylnaphthalenesulfonic acid or also sodium salt of oleylmethyltauric acid. To produce spray powders, the herbicidally active substance is finely ground, for example, in a conventional apparatus such as a hammer mill, bubble mill or air-jet mill and is mixed simultaneously or subsequently with auxiliaries.

Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, such as, for example, butyl alcohol, cyclohexanone, dimethylformamide, xylene, or also higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of the ionic and/or non-ionic type (emulsifiers). For example, calcium salts of alkylarylsulfonic acids, such as calcium dodecylbenzenesulfonate, or non-ionic emulsifiers, such as fatty acid polyglycol esters, alkylarylpolyglycol ethers, poly- 67

• · • · · · · · · · · · « · • · · * glycol ethers of fatty alcohols, condensation products of propylene oxide and ethylene oxide, alkyl polyethers, sorbitan esters, such as fatty acid esters of sorbitol, or polyoxyethylene sorbitan esters, such as fatty acid esters of polyoxyethylene sorbitol.

Dusts are obtained by grinding the active ingredient with finely divided solids, such as talc, natural earths such as kaolin, bentonite or pyrophyllite, or also diatomaceous earth.

Suspension concentrates can be water- or oil-based. They can be produced, for example, by wet milling using commercially available bead mills and optionally with the addition of surfactants, which have already been mentioned above for other types of formulations, for example.

Emulsions, for example of the oil-in-water (EW) type, can be produced, for example, using stirrers, colloid mills and/or static mixers, using aqueous organic solvents and optionally surfactants, which have been, for example, already mentioned above for other types of formulations.

Granules can be produced either by spraying the active substance onto an adsorbable, granular inert material, or by applying an active substance concentrate with the aid of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils, onto the surface of carrier substances such as sand, kaolinite or granular inert material. Suitable active substances can also be granulated in a manner customary for the production of granular fertilizers, optionally in a mixture with fertilizers.

Water-dispersible granules are usually

- 68 are produced using conventional methods such as spray drying, fluidized bed granulation, plate granulation, mixing in high-speed mixers and extrusion without solid inert material.

For the production of granulates produced by plate granulation, fluidized bed granulation, extrusion and spray granulation, see, for example, the methods described in Spray-Drying Handbook 3rd ed. 1979, G. Goodwin Ltd., London; J. E. Browning, Agglomeration, Chemical and Engineering 1967, p. 147 et seq.; Perry’s Chemical Engineer’s Handbook, 5th Ed., McGrawHill, New York 1973, p. 8-57.

Further details for the formulation of plant protection products are given, for example, in G. C. Klingman, Weed Control as a Science, John Viley and Sons, Inc., New York, 1961, pp. 81-96 and J. D. Freyer, S. A. Evans, Weed Control Handbook, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

Agrochemical preparations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of the active ingredient of the general formula I.

In wettable powders, the concentration of active ingredient is, for example, about 10 to 90% by weight, the remainder up to 100% by weight consisting of customary formulation components.

In emulsifiable concentrates, the concentration of active ingredient may be about 1 to 90% by weight, preferably 5 to 80% by weight.

Powder formulations contain 1 to 30% by weight, • · · » • · · · • · ♦ · »

- 69 preferably mostly 5 to 20% by weight of active ingredient.

Sprayable solutions contain about 0.05 to 80% by weight, preferably 2 to 50% by weight, of the active ingredient.

In water-dispersible granules, the active ingredient content depends in part on whether the active compound is present in liquid or solid form and on which granulation auxiliary, filler, etc. is used. In water-dispersible granules, the active ingredient content is, for example, in the range of 1 to 95% by weight, preferably 10 to 80% by weight.

In addition, the active ingredient formulations contain, if appropriate, conventional adhesion promoters, wetting agents, dispersants, emulsifiers, penetrating agents, preservatives, antifreeze agents and solvents, fillers, carriers and colorants, defoamers, evaporation suppressants and substances influencing the pH value and viscosity.

On the basis of these formulations, combinations with other pesticidally active substances, such as insecticides, acaricides, herbicides, fungicides, safeners, fertilizers and/or growth regulators, can also be produced, for example in the form of ready-made preparations or tank mixtures.

Combination partners for the active ingredients according to the present invention in mixed formulations or in tank mixtures include, for example, the known active ingredients which are described in Veed Research 26, 441-445 (1986) or The Pesticide Manual, 9th ed., The British Crop Protection Council, 1990/91, Bracknell, England and in the literature cited therein. The following active ingredients may be mentioned as herbicides known from the literature which can be combined with compounds of the general formula I (note: The compounds are designated either by the so-called common name according to the International Organization for Standardization (ISO) or by the chemical name, optionally together with the usual code number):

Acetochlor; acifluorfen; aclonifen; AKH 7088, i.e. [[[1-[5-[2-chloro-4-(trifluoromethyl)-phenoxy]-2-methoxyethylidene]-amino]-oxy]-acetic acid and [[[1-[5-[2-chloro-4-(trifluoromethyl)-phenoxy]-2-methoxyethylidene]-amino]-oxy]-acetic acid; alachlor; alloxydim; ametryn; amidosulfuron; amitrole; AMS, i.e. ammonium sulfamate; anilophos; asulam; atrazine; azimsulfurone (DPX-A8947); aziprothrin; barbarian; BAS 516 H, i.e. 5-fluoro-2-phenyl-4H-3,1-benyoxayin-4-one; benazoline; benfluralin; benfuresate; bensulfuron-methyl; bensulide; bentazone; benzofenap; benzofluorine; benzoylprop-ethyl; benzthiazuron; bialaphos; bifenox; bromacil; bromobutide; bromophenoxime; bromoxynil; bromuron; buminaphos; busoxinone; brtachlor; butamiphos; bethenachlor; buthidazole; butraline; butylate; cafenstrole (CH-900); cafentrazone (ICI-A0051); carbetamide; CDAA,

i.e. 2-chloro-N,N-di-2-propenylacetamide; CDEC, i.e. diethyldithiocarbamic acid 2-chloroallyl ester; chlomethoxyphen; chloramben; chlorazifop-butyl, pirifenop-butyl; chlormesulone (ICI-A0051); chlorbrumuron;

chlorbufam; chlorfenac; chloroflurecol-methyl; chloridazone; chlorimuron ethyl; chlornitrofen; chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlorthal-dimethyl; chlorthiamid; cinmethylin; cinosulfuron; clethodim; clodinafop and its ester derivatives (for example, clodinafoppropargyl); clomazone; clomeprop; cloproxydim; clopyralid;

cumyluron (JC 940); cyanazine; cycloate; cyclosulfamuron (AC 104); cycloxydim; cycluron; cyhalofop and its ester derivatives (e.g. butyl ester, DEH-112); cyperquat;

cyprazine; cyprazole; diamuron; 2,4-DB; dalapon;

desmedipham; desmetryn; di-allate; dicamba; dichlobenil; dichloroprop; diclofop and its esters, such as diclofop-methyl; diethyl; difenoxuron; difenzoquat; diflufenican; dimefuron; dimethachlor; dimethamethrin; dimethamethrin; dimethenamid (SAN-582H); dimethasone, clomazone; dimethipine;

dimetrasulfuron, cinosulfuron; dinitramine; dinoseb; dinoterb; diphenamide; dipropetryn; diquat; dithiopyr; diuron; BOTTOM; eglinazine-ethyl; EL 177, i.e. 5-cyano-1-(1,1-dimethylethyl)-N-methyl-3H-pyrazole-4-carboxamide; endothallus; EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl; ethidimuron; ethiosias; ethofumesate; F5231, i.e. N-[chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-ΙΗ-tetrazol-1-yl]-phenyl]-ethanesulfonamide; ethoxyphene and its esters (eg ethyl ester, HN-252); etobenzanide (HV 52); fenoprop; fenoxane, fenoxaprop and fenoxaprop-P, as well as their esters, for example fenoxaprop-P-ethyl and phenoxypropethyl; phenoxydim; fenuron; flamprop-methyl; flazasulfuron; fluazifop and fluazifop-P and their ester derivatives, for example fluazifop-butyl and fluazifop-P-butyl; fluchloralin; flumetsulam; flumeturon; flumiclorac and its esters (for example pentyl ester, S-23031); flumioxazine (S-482); flumipropyn; flupoxam (KNV-739); fluorodifen; fluoroglycofen-ethyl; fluropacil (UBIC-4243); fluridone; flurochloridone;

fluroxypyr; flurtamone; fomesafen; fosamine; furyloxyphene; glufosinate; glyphosate; halosaten; halosulfuron and its esters (eg methyl ester, NC-319); haloxyfop and its ester derivatives; haloxyfop and its esters; haloxyfop-P (= R-haloxyfop) and its esters; hexazinone;

imazamethabenz-methyl; imazapyr; imazaquin and its salts, for example the ammonium salt; imazethamethayr; imazethapyr;

imazosulphoron; ioxynil; isocarbamide; isopropaline;

isoproturon; isouron; isoxaben; isoxapyrifop; carbutylate; lactofen; lenacil; linuron; MCPA; MCPB; mecoprop; mefenacet; mfluidide; metamitron; metazachlor; methabenzthiazuron; meth; methazole; methoxyphenone; methyldymrone;

metabenzuron; methobenzuron; metobromuron; metolachlor; metosulam (XRD 511); metoxuron; metribuzin; metsulfuronmethyl; MH; molinate; monalides; monocarbamide dihydrogensulfate; monolinuron; monuron; MT 128, i.e. 6-chloro-N-(3-chloro-2-propenyl)-5-methyl-N-phenyl-3-pyridayinamine; MT 5950; i.e. N-[3-chloro-4-(1-methylethyl)-phenyl]-2-methylpentanamide; naproanilide; napropamide; I asked; NC 310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole; neboron; nicosulfuron; nipyraclofen; nitraline; nitrofen; nitrofluorfen; norflurazone; orbencarb; oryzalin; oxadiargyl (RP-020630); oxadiazone; oxyfluorfen; paraquat; pebulate;

pendimethalin; perfluidone; phenisopham; phenmedipham; picloram; piperophos; piributicarb; pirifenop-butyl; pretilachlor; primisulfuron-methyl; procyazine; prodiamine; profluralin; proglinazine-ethyl; promethone; promethrin; propachlor; propanil; propaqizafop and its ester derivatives; propazine; propham; propisochlor; propyzamide; prosulfaline; prosulfaline; prosulfocarb; prosulfuron (CGA-152005); prynachlor; pyrazolinates; pyrazone; pyrazosulphoron-ethyl; pyrazoxyfen; pyridates; pyrithiobac (KIH-2031); pyroxofop and its ester derivatives (eg propargyl ester); quinclorac;

quinmerac; quinofop and its ester derivatives, quizalofop and quizalfop-P and their ester derivatives, for example quizalofop-ethyl; quizalofop-P-tefuryl and quizalofop-P-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 2-[[7-[2-chloro-4-(trifluoromethyl)-phenoxy]-2-naphthalenyl]-oxy]-propanoic acid methyl ester; sulfentrazone (FMC-97285, F-6285); sulfometuron-methyl; sulfazuron; sulfosate (ICI-A0224);

TCA; tebutam (GCP-5544); tebuthiuron; terbacil; terbucarb;

terbuchlor; terbumetone; terbuthylazine; terbutryn; TFH 450, i.e. N,N-diethyl-3-[(2-ethyl-6-methylphenyl)-sulfonyl]-1H-1,2,4-triazole-1-carboxamide; thenyl chloride (NSK-850); thiazafluron; thizopyr (Mon-13200); thidiazimine (SN-24085);

thifensulfuron-methyl; thiobencarb; thiocarbazil;

tralkoxydim; tri-allate; triasulfuron; triazofenamide; tribenuron-methyl; triclopyr; tridiphane; triethazine; trifluralin; triflusulfuron and its esters (eg methyl ester, DPX-66037); trimethuron; cytodef; vernolate; VL

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; DOVCO-535;

DK-8910; V-53482; PP-600; MBH-001; KIH-9201 ; ET-751; KIH-6127 and KIH-2023.

For use, the commercial forms of the preparations mentioned are optionally diluted in the usual manner, for example in the case of sprayable powders, emulsifiable concentrates, dispersions and water-dispersible granules with water, and then applied to plants, parts of plants, or agriculturally or industrially used soils on which the plants stand or from which they grow or where they occur as seeds. Powder preparations, soil or spray granules, and sprayable solutions are usually not diluted with other inert substances before use.

The required application amount of the compounds of the general formula I varies with external conditions such as temperature, humidity, type of herbicide used, among other things. It can vary within a wide range, for example between 0.001 and 10.0 kg/ha or more of active substance, but is preferably 0.005 to 5 kg/ha.

The following examples illustrate the invention in more detail.

Examples of embodiments of the invention

A) Chemical examples

Example A1

2-Amino-4-fluoroisopropyl-6-[N-(1-methyl-3-phenoxy-prop-1-yl)-amino]-1,3,5-triazine (see Table 2, Example 368)

0.45 g (0.019 mol) of sodium is dissolved in 50 ml of anhydrous methanol. 1.85 g (0.006 mol) of 3-biguanido-1-phenoxybutane hydrochloride and then 1.3 g (0.010 mol) of ethyl fluoroisobutyrate are added. The reaction mixture is heated to reflux for 3 hours, the solvent is evaporated off in vacuo, the residue obtained is taken up in a dichloromethane/water mixture and extracted several times. The organic phase is separated, dried over anhydrous magnesium sulfate, filtered and the solvent is removed in vacuo. After purification by column chromatography on silica gel using ethyl acetate/heptane (1:1), 0.45 g (24%) of the title compound is obtained.

Example A2

2-Amino-4-isopropyl-6-{N-[1-methyl-2-(4-chlorobenzyloxy)-eth•

- 75 l, example 166) of 2-ami· hydrochloride with 2.34 g (0.017 (0.004 mol) of 2-amihyl]amino}-1,3,5-triazine (see table

1.00 g (0.004 mol) of nor-propyl-4-chlorobenzyl ether together with (mol) of potassium carbonate and 0.73 g of nor-4-chloro-6-isopropyl-1,3,5-triazine are introduced and the mixture is heated to reflux for 3 hours. The solvent is then removed in vacuo and the residue obtained is taken up in ethyl acetate/water and extracted several times. The organic phase is separated, dried over anhydrous magnesium sulfate, filtered and the solvent is removed in vacuo. After purification by column chromatography on silica gel using ethyl acetate/heptane (1:1), 1.20 g (89%) of the title compound are obtained.

Example A3

2-Amino-4-isopropyl-6-{N-[2-(3,4-dichlorobenzyloxy)-ethyl]amino}-1,3,5-triazine

0.5 g (0.0024 mol) of 3,4-dichlorobenzoic acid chloride in 30 ml of 1,4-dioxane are introduced and 0.47 g (0.0024 mol) of 2-amino-4-isopropyl-6-[2-(hydroxyethyl)-amino-1,3,5-triazine are added. The reaction mixture is heated to reflux for 4 hours, the precipitated solid is filtered off and the solvent is evaporated off in vacuo. The residue obtained is taken up in ethyl acetate/water and extracted several times. The organic phase is separated, dried over anhydrous magnesium sulfate, filtered and the solvent is removed in vacuo. 0.65 g (73%) of the title compound is thus obtained.

Exemplary compounds listed in the following tables

in the same way as above.

The abbreviations used in the following tables mean:

Et = ethyl

Me = methyl c = cyclo n = normal i = iso s = secondary t = tertiary

F.P. = freezing point

An unsymmetrical divalent group Y , such as Y = C(0)0 (i.e. (-C0-0-) ), refers in the tables to a group whose bonding site on the atom of the group shown on the left is connected to the part of the molecule shown on the left in formula I.

• ·

- 77 Table 1

Compounds of general formula Ia (= formula I , where η = 1 , R ¹ , R ² , R ³ , R ² , R^ and R^-θ = hydrogen atom and Aryl = substituted phenyl according to the table)

R ⁶

NH.

(CH ₂ ) _m -Y - CR ³ R- CH- N

N

N=<

'F

R (la)

No. From m Y R ³ R ⁴ R ^S R ⁸ physical data 1 2,4-CI ₂ 0 C(O)O H H Me i-Propyl oil From 2,4-CI ₂ 0 C(O)O H H Et i-Propyl oil 3 2,4-CI ₂ 0 C(O)O H H H i-Propyl oil 4 2,4-CI ₂ 0 C(O)O H H Me cf ₃ 5 2,4-F ₂ 0 C(O)O H H Me i-Propyi oil 6 2,4-F ₂ 0 C(O)O H H And i-Propyl oil 7 2,4-F ₂ 0 C(O)O H H H i-Propyl oil 8 2,4-F ₂ 1 C(O)O H H n-Eutyi cf ₂ chf ₂ 9 2.5-F ₂ 0 C(O)O H H Me i-Propyl oil 10 2.5-F ₂ 0 C(O)O H H Et i-Propyl oil 11 2.5-F ₂ 0 C(O)O H H H i-Propyl oil 12 2.5-F ₂ 1 C(O)O H H H CF(CH ₃ ) ₂ 13 2,6-F ₂ 0 C(O)O H H Me i-Propyl oil 14 2,6-F ₂ 0 C(O)O H H Et i-Propyl oil 15 2,6-F ₂ 0 C(O)O H H H i-Propyl oil 16 2,SF ₂ 1 C(O)O H H Me cf ₃ 17 2-CF ₃ 0 C(O)O H H Et i-Propyl 18 2-CI 0 C(O)O H H Me i-Propyl oil 19 2-CJ 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 CF ₂ CHF ₂ 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

• ·

No. From m Y R ³ R ⁴ R ⁶ R ⁸ physical data 25 2-CI.4-F 0 C(O)O Me H Me CF(CH ₃ ) ₂ 26 2-Cl,4-NO ₂ 0 C(O)O H H Me i-Propyl oil 27 2-Cl,4-NO ₂ 0 C(O)O H H Et i-Propyl oil 28 2-Cl,4-NO ₂ 0 C(O)O H H H i-Propyl oil 29 2-Cl,4-NO ₂ 0 C(O)O H H t-Sutyl i-Propyi 30 2-CI.5-NO2 0 C(O)O H H Me i-Propyl oil 31 2-Cl,5-NO ₂ 0 C(O)O H H Et i-Propyl oil 32 2-Cl,5-NO ₂ 0 C(O)O H H H i-Propyl oil 33 2-Cl,5-NO ₂ 0 C(O)O H H Me CF(CH ₃ ) 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-Propyi oil 36 2-F 0 C(O)O H H H i-Propyi oil 37 2-F 0 C(O)O Me H _CH2OEt Cr(CH ₃ ) ₂ 38 2-F,3-CF ₃ 0 C(O)O H H Et i-Propyl 39 2-F,4-CF ₃ 0 C(O)O H H Et i-Propyl 40 2-F,5-CF ₃ 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-Fropy! oil 44 2-Me 2 C(O)O H H CH ₂ -c-Propyl CP(CK ₃ ) ₂ 45 2-OAc 0 C(O)O H H Me i-Prcpyi oil 46 2-OAc 0 C(O)O H H Electric i-Propyl oil 47 2-OAc 0 C(O)O H at H i-Propyl oil j 48 2-OAc 1 C(O)O Me H c-Fenty ckfch ₃ 49 3,4-CJ ₂ 0 C(O)O H H Me i-Propyl oil 50 3,4-Cl ₂ 0 C(O)O H H Et i-Propyl oil 51 3.4-02 0 C(O)O H H H i-Propyl oil 52 3,4-O ₂ 0 C(O)O H H s-Shoes chfcf ₃ 53 3,5-( _CF3 ) ₂ 0 C(O)O H H Et i-Propyl 54 3,5-Cl ₂ 0 C(O)O H H Me i-Propyl oil 55 3.5-CI ₂ 0 C(O)O H H Et i-Propyl oil 56 3.5-CI ₂ 0 C(O)O H H H i-Propyl oil 57 3.5-CI ₂ 0 C(O)O H H _CH2OMe chfch ₃ 58 3.5-F ₂ 1 Sat ₂ Me H Me cf ₂ chf ₂

No. From m Y R ³ R ⁴ L R ⁶ R ⁸ physical data 59 3.5-F ₂ 2 0 H H í Et cf ₂ chf ₂ 60 3.5-F ₂ 1 0 H H c-Eutyl cf ₂ chf ₂ 61 3.5-F ₂ 1 0 H H H _{CF2CHr2 ​} 62 3,5-Me ₂ 1 C(O)O Et H H CF ₂ CHF ₂ 63 3,5-Me ₂ 1 0 H H! Me i-Propyl t. t.80°C 64 3,5-Me ₂ 1 0 H H Me CF(CH ₃ ) ₂ resin 65 3.5-Mβ2 1 0 Me H Et CHFCH3 66 3,5-Me ₂ 1 0 H H c-Butyl CF ₂ CHF ₂ 67 3,5-Me ₂ 1 0 H H c-Pentyl CF(CH ₃ ) ₂ 66 3,5-Me ₂ 1 0 Et H H cf ₂ ckf ₂ 69 3,5-(OMe) ₂ 1 C(O)O Me H H CHFCH3 70 3,5-(OMe) ₂ 1 0 H H Me CFa 71 3,5-(OMe) ₂ 1 with Me H Et CF(CH ₃ ) ₂ 72 3,5-(OMe) ₂ 1 Sat ₂ H H c-Butyl CHFCH3 73 3,5-(OMe) ₂ 1 0 H H c-Pentyl i-Propyl 74 3,£-{GWe) ₂ 1 Sat ₂ Me H H CHFCH ₃ 75 3-Er 1 0 ^H H Me i-Propyi resin 76 3-Br 1 0 H H Me CF(CH ₃ ) ₂ t.t.iorc 77 3-Br 1 0 To H Me CF ₂ CHF ₂ mp128°C 78 3-CF ₃ 0 C(O)O H H Me i-Propyi oil 79 3-CF3 0 C(O)O H H Et i-Propyl oil 80 3-CF ₃ 0 C(O)O H H H i-Propyi oil 81 3-CF3 ¹ Sat ₂ To H Et cf ₃ 32 3-CFs 1 0 H H c-Propyl chfch ₃ 83 3-CF3 2 0 H H c-Eutyi i-Propyl 84 3-Cl 0 C(O)O H H Me i-Propyi oil 85 3-Cl 0 C(O)O H H Et i-Fropyl oil 86 3-CI 0 C(O)O H H H i-Propyl oil 87 3-Cl 0 C(O)O H H cf ₃ CF ₂ CHF ₂ 83 3-Cl 1 C(O)O H H H CF(CH3) ₂ 89 3-Cl 1 0 H H Me i-Fropyl resin 90 3-Cl 1 0 H H Me CF(CH ₃ ) ₂ resin 91 3-Cl 1 0 H H Me cf ₂ chf ₂ mp103 °C 92 3-CI 1 0 H H Et cf ₃

• · • · · · • · · · • · ·

No. From m Y R ³ R ⁴ R ^S R ⁸ physical data 93 3-CI 1 Sat ₂ H H c-Butyl CF(CH ₃ ) ₂ 94 3-CI 1 Sat ₂ H H c-Pentyl cf ₂ chf ₂ 95 3-CI 1 Sat ₂ H H H CF(CH ₃ ) ₂ 96 3-Cl,5-Me 1 0 c-Propyl H Et cf ₂ chf ₂ 97 3-Cl,5-Me 1 about H H c-Propyl cf ₃ 98 3-Cl,5-Me 1 about H H c-Butyl CHFCH ₃ 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 about H H Me i-Propyl 105 3-F 2 0 H H Et i-Propyl 106 3-F 2 0 H H c-Butyl i-Propyl 107 3-F 2 about c-Propyl H H i-Propyl 108 3-F,4-CF ₃ 0 C(O)O H H Et.. i-Propyl 109 3-F,5-Cr ₃ 0 C(O)O H H Et i-Propyl 110 3-F,5-Me 2 0 H H Me i-Propyl 111 3-F,5-Me 1 about H H Et ckfch ₃ 112 3-F,5-Me 2 about {—' H c-Propyl i-Propyi 113 3-F,5-Me 1 with H H c-Butyl CF(CH ₃ ) ₂ 114 3-F,5-OMe 2 with To H Me cf ₂ ckf ₂ 115 3-F,5-OMe 1 0 H H Et CF(CK ₃ ) ₂ 116 3-F,5-OMe 2 with To H c-Propyl cf ₂ chf ₂ 117 3-F,5-OMe 1 Sat ₂ H H c-Butyl cf ₃ 118 3-Me 1 C(O)O H H H cf ₃ 119 3-Me 1 0 H H Me i-Propyl resin 120 3-Me 1 about H H Me CF(CH ₃ ) ₂ mp 112°C 121 3-Me 1 about H H Me cf ₂ chf ₂ resin 122 3-Me 1 about H H Et CF(CH ₃ ) ₂ 123 3-Me 1 about H H c-Eutyl cf ₃ 124 3-Me 1 0 H H c-Pentyl cf ₂ chf ₂ 125 3-Me 1 about H H H cf ₃ 126 3-Me,4-F 2 0 H H Me chfch ₃

• ·

No. From m Y R ³ R ⁴ R ^S R ³ physical data 127 3-Me,4-F 2 Sat ₂ H H Et CF(CH ₃ ) ₂ 128 3-Me,4-F 1 0 H H c-Propyl CHFCH3 129 3-Me,4-F 1 0 H H c-Butyl CF(CH ₃ ) ₂ 130 3-Me,4-F 1 0 c-Propyl H H CF(CH ₃ ) ₂ 131 3-OCF ₃ 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(CH ₃ ) ₂ 135 3-OEt 2 0 c-Propyl H Me CF(CH ₃ ) ₂ 136 3-OEi 2 with H H Et i-Propyl 137 3-OEt 2 0 Et H c-Propyl CF(CH ₃ ) ₂ 138 3-OEt 1 0 Me H c-Butyl cf ₃ 139 3-OMe 1 C(O)O H H H i-Propyl 140 3-OMe ¹ with H H Me CF(CH ₃ ) ₂ 141 3-OMe 11 0 H H Et cf ₃ 142 3-OMe 1 0 H To c-Eutyi i-Propyl 143 3-OMe 1 0 c-Prcpyl H c-Pentyl CHFCH ₃ 144 3-OMe 1 0 H H H i-Propyl 145 3-OMe,5-C! 2 0 H H Et CHFCH ₃ 146 3-OMe,5-C! 2 with H H c-Eutyl CHFCH.3 147 3-OMe,5-C! 2 with Me Me H CHFCK3 14S 4-Br 0 C(O)O H H Me i-Propyl oil 149 4-Br 0 C(O)O To H Et i-Propyl oil 150 4-Br 0 C(O)O ^{H H} H i-Propyi oil 151 4-Br 1 C(O)O Me H c-Pentyl CHFCH ₃ 152 4-Br 1 0 H H Me i-Propyl mp82 'C 153 4-Br 1 0 H H Me CF(CH ₃ ) ₂ resin 154 4-Br 1 0 H H Me cf ₂ chf ₂ mp114°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

« ·

No. From m Y R ³ R ⁴ R ⁸ R ³ physical data 161 4-CF ₃ 0 C(O)O H H CH2-c-Butyl cf ₃ 162 4-Cl 0 C(O)O H H Me i-Propyl oil 163 4-Cl 0 C(O)O H H Et i-Fropyl oil 164 4-Cl 0 C(O)O H H H i-Propyl oil 165 4-Cl 0 C(O)O H H _CH2F chfch ₃ 166 4-Cl 1 0 H H Me i-Propyl resin 167 4-Cl 1 0 H H Me CF(CH ₃ ) ₂ resin 168 4-Cl 1 0 H H Me cp ₂ chf ₂ mp104 °C 169 4-F 0 C(O)O H H Me i-Propyl oil 170 4-F 0 C(O)O H H Electric i-Propyi oil 171 4-F 0 C(O)O H H H i-Fropyl oil 172 4-F 1 C(0)O H H t-Eutyl 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 4-1 0 C(O)O H To H i-Propyi oil 177 4-i 0 C(O)O To H H CF(CH ₃ ) ₂ 173 4-Me 0 C(O)O H H Me i-Propyi oil 173 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-Propyi i-Propyi 182 4-Me 1 0 H H Me i-Propyi resin 183 4-Me 1 0 To H Me CF(CH ₃ ) 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(CH ₃ ) 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

C ·· » Mi· « · · · • · • · • · * » · i r e

φ

No. From m Y R ³ R ⁴ R ⁶ R ⁸ physical data 195 4-t-Bu 0 C(O)O Me H s-Butyl CF(CH ₃ ) 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(CH ₃ ) ₂ 200 H 1 about H H Me i-Propyl mp104 °C 201 H 1 0 H H Me CF(CH ₃ ) ₂ resin 202 H 1 about H H Me cf ₂ chf ₂ 1.1.118 °C 203 H 1 about Me H Me chfch ₃ 204 H 1 Sat ₂ Me H Et CHFCH ₃ 205 H 1 about Me H c-Butyl CF(CH ₃ ) ₂ 206 H 1 about Me Me H CF(CH ₃ ) ₂

Table 2

Compounds of general formula Ib (— formula I , where n — 2 , R , R ² , R^, R ² , R^ _and R ¹ ® = hydrogen atom and Aryl = substituted phenyl according to the table)

NH.

/-(CH ₂ ) _m —Y— CH ₂ — CR ³ R ⁴ — _CH — N // n (Ib)

l no. From m Y R ³ R ⁴ R ⁶ R ⁸ physical data 207 3.5-F ₂ 0 about H H Me CF(CH ₃ ) ₂ resin 208 3,5-(OMe) ₂ 0 about H H t-Butyl i-Propyl 209 3-CI 0 about H H Me i-Propyl resin 210 3-F 0 about Et Et H CF ₂ CHF ₂ 211 3-Me 0 0 H H c-Propyl cf ₂ chf ₂ 212 3-Me,4-F 0 about H H Me CF(CH ₃ ) ₂ resin 213 3-OMe 0 about H H Me i-Propyl resin 214 H 0 0 Me Me H i-Propyl oil 215 3.4,5-CI ₃ 1 about H H c-Pentyl CHFCH ₃

No. From m Y R ³ R ⁴ R ⁶ R ^S physical data 216 3.5-F ₂ 0 0 H H Et cf ₂ chf ₂ resin 217 3,5-Me ₂ 0 about H H Electric CF(CH ₃ ) ₂ resin 218 3-CF ₃ 1 C(O)O H H Me chfch ₃ 219 3-CI 0 0 H H c-Propyl cf ₂ chf ₂ 220 3-CI 0 0 H H Et chfch ₃ resin 221 3-Cl,5-Me 1 About H H CH ₂ -cSutyl i-Prcpyi 222 3-F 0 About H H Et CF(CH ₃ ) ₂ resin 223 3-F 0 About Hey H H chfch ₃ 224 3-Me 0 About Me Me H i-Propyl 225 3-Me 0 About Me H Me CF(CK ₃ ) ₂ resin 226 3-Me,4-F 0 0 H H Et chfch ₃ resin 227 3-Me,4-F 0 0 H H c-Propyl cf ₂ chf ₂ resin 228 3-OMe 0 0 H H Et cf ₂ chf ₂ resin 229 3-OMe,5-CI 1 0 H H n-Buty cf ₂ chf ₂ 230 H 0 0 Me H Me CF(CH ₃ ) ₂ 231 H 0 about H H Et i-Propyl resin 232 3.5-F ₂ 0 about H H c-Fropyi CF ₂ CHF ₂ 3,5-(OEt) ₂ 4 1 with H H _CH20Me chfch ₃ 234 3-Cl 0 about Me H Me CHFCH ₃ resin 235 3-F 0 0 Hey Electric H CF(CH ₃ ) ₂ 236 3-Me 0 0 H H c-Propyl CF(CH ₃ ) ₂ resin 237 3-Me 0 Sat ₂ H H i-Fropyl i-Propyl 238 3-OMe 0 about H H c-Eutyl chfch ₃ 239 H 0 about H H c-Eutyl chfch ₃ resin 240 3.5-F ₂ 0 about H H c-Propyl chfch ₃ 241 3,5-(OEi) ₂ 0 0 H H CH ₂ -cBuyl cf ₂ chf ₂ 242 3-CI 0 about Me H Me CF(CH ₃ ) ₂ resin 243 3-F 0 about Electric Electric H i-Propyl 244 3-Me 0 about H H c-Propyl i-Propyl resin 245 3-Me 0 0 H H Et CF(CH ₃ ) ₂ resin 246 3-OMe 0 c H H c-Butyl CF(CH ₃ ) ₂ 247 H 0 0 H H c-Butyl CF(CH ₃ ) ₂ 248 3.5-CI ₂ 0 0 H Et i-Propyl i-Propyl 249 3,5-(OEt) ₂ 1 about H H n-Butyl CF ₂ CHF ₂

No. From m Y R ³ R ⁴ R ⁶ R ⁸ physical data 250 3-Cl 0 About Me Me H CHFCH ₃ 251 3-F 0 about H H c-Butyl CF(CH ₃ ) ₂ 252 3-F,5-OMe 1 0 H H s-Butyl i-Propyl 253 3-Me 0 0 H H Me CF(CH ₃ ) ₂ resin 254 3-OEt 1 C(O)O H H CH ₂ -cButy i-Propyl 255 H 0 0 H H c-Propyl chfch ₃ resin 256 3,4.5-CI ₃ 0 about H H cf ₃ CHFCH ₃ 257 3.5-CI ₂ 0 about H H _CH2OEt CF(CH ₃ ) ₂ 258 3,5-Cl ₂ 1 Sat ₂ H H Me cf ₃ 259 3,5-Me ₂ 0 about H H c-Fentyl chfch ₃ 260 3,5-(OEt) ₂ 0 about H H Me CHFCF ₃ 261 3,5-(OEt) ₂ 0 C(O)O H H i-Propyi i-Propyl 262 3-Cl 0 About H H c-Butyl CHFCH ₃ 263 3-Cl 0 about Me Me H i-Propyl resin 264 3-Cl 0 0 Me Me H CF(CH ₃ ) ₂ resin 265 3-F 0 about H H c-Propyl CF(CH ₃ ) ₂ 266 3-F 0 about H H c-Propyl cf ₂ chf ₂ 267 3-F 0 about H H c-Butyl i-Propyl 268 3-F,5-Me 0 SO2 H H Me CF(CH ₃ ) ₂ 269 3-F,5-Me 0 about H H n-Butyl cf ₂ chf ₂ 270 3-F,5-OMe 0 C(O)O H H c-Pentyl cf ₃ 271 3-Me 0 0 Me H H i-Propyl resin 272 3-Me 0 0 Me H H CF ₂ CHF ₂ resin 273 3-Me 0 about H H Me i-Propyl resin 274 3-Me,4-F 0 about H H c-Butyl chfch ₃ resin 275 3-OEt 2 about H H _CH2F i-Propyl 276 3-OEt 0 about H H CH ₂ -c-Propyl cf ₃ 277 3-Ph 1 Sat ₂ H Me t-Butyl i-Propyl 278 H 0 about H H c-Propyl i-Propyl resin 279 H 0 about H H c-Propyl CF(CH ₃ ) ₂ resin 280 H 0 about H H Me cf ₃ 281 3.5-F ₂ 0 about H H Me i-Propyl resin 282 3,5-Me ₂ 0 about H H Me CF(CH ₃ ) ₂ t. t.131’C 283 3,5-(OMe) ₂ 0 C(O)O H H s-Butyl chfcf ₃

No. From m Y R ³ R ⁴ R ⁶ R ⁸ physical data 284 3-0 0 0 H H c-Propyl i-Propyl resin 285 3-0 0 0 Me H Me CF ₂ CHF ₂ resin 286 3-0 0 0 H H CH ₂ -c-Propyl CF(CH ₃ ) ₂ 287 3-F 0 about Et Et H chfch ₃ 288 3-F 0 about H H _CH2 -c-Butyl cf ₃ 289 3-Me 0 0 H H c-Propyl chfch ₃ resin 290 3-Me 0 about Me Me H chfch ₃ 291 3-Me,4-F 0 about H H Me i-Propyl resin 292 3-Me,4-F 0 0 H H c-Propyl i-Propyl resin 293 3-OMe 0 about H H c-Butyl cf ₂ chf ₂ 294 3-OMe,5-0 0 about H H Me i-Propyl resin 295 H 0 about H H c-Butyl cf ₂ chf ₂ 296 H 0 about Me H Me cf ₂ chf ₂ 297 3.5-F ₂ 0 about H H Me cf ₂ chf ₂ resin 298 3,5-(OMe) ₂ 0 0 H Me cf ₃ cf ₂ chf ₂ 299 3-CI 0 0 H H Me CF(CH ₃ ) ₂ !resin 300 3-F 0 about H H Me i-Propyi resin 301 3-Me 0 about H H c-Butyl i-Propyl resin 302 3-Me,4-F 0 0 H H Me chfch ₃ 303 3-OMe 0 about H H Me CF(CH ₃ ) ₂ resin 304 H 0 about Me Me H CF(CH ₃ ) ₂ resin 305 3.5-F ₂ 0 about H H Et i-Propyl resin 306 3,5-(OMe) ₂ 0 0 H H _CH2F chfch ₃ 307 3-0 0 about H H Me cf ₂ chf ₂ resin 308 3-F 0 0 H H Me CF(CH ₃ ) ₂ resin 309 3-Me 0 0 H H c-Butyl CF(CH ₃ ) ₂ resin 310 3-Me,4-F 0 about H H Me cf ₂ chf ₂ resin 311 3-OMe 0 about H H Me cf ₂ chf ₂ resin 312 H 0 about Me Me H chfch ₃ resin 313 3,5-Cl ₂ 0 SO2 H H _CH2OMe chfch ₃ 314 3.5-{OEt) _from 0 about H H CH ₂ OEí chfch ₃ 315 3-0 0 about H H c-Butyl cf ₂ chf ₂ 316 3-F 0 about H H c-Propyl chfch ₃ 317 3-F,5-Me 0 about H H i-Propyl i-Propyl

No. From m Y R ³ R ⁴ R ^S R ⁸ physical data 318 3-Me 0 0 Me H H CF(CH ₃ ) ₂ ^resin 319 3-Me,4-F 0 about H H c-Butyl cf ₂ chf ₂ 320 3-Ph 0 0 H π Cr ₃ cf ₂ chf ₂ 321 3.5-F ₂ 0 about H H c-Propyl i-Propyl 322 3,5-(OEt) ₂ 0 with H H _CH2F chfcf ₃ 323 3-CI 0 about Me Me H cf ₂ chf ₂ 324 3-F 0 about H H c-Butyl CHFCH ₃ 325 3-F,5-OMe 0 about H H t-Butyl CF ₂ CHF ₂ 325 3-Me 0 about H H Me cf ₂ chf ₂ resin 327 3-OEt 1 about H Et _CH2OMe cf ₂ chf ₂ 328 H 0 about H H c-Fropyl cf ₂ chf ₂ 329 3,5-Me ₂ 0 about H H Me cf ₂ chf ₂ resin 330 3-CJ 0 about H H c-Propyl CF(CH ₃ ) ₂ resin 331 3-Cl,5-Me 1 C(O)O H Me _CH2F CF(CH ₃ ) ₂ 332 3-F 0 0 H H H i-Propyl 333 3-Me 0 about Me Me H cf ₂ chf ₂ 334 3-Me,4-F 0 c H H c-Propyl CF(CH ₃ ) ₂ resin 335 3-OMe,5-Cl 0 0 H H Me CF(CH ₃ ) ₂ resin 336 H 0 about H H Me i-Propyl resin 337 3,4,5-CI ₃ 0 with H H s-Butyl CF(CK ₃ ) ₂ 338 3.5-F ₂ 0 about H H c-Propyl CF(CH ₃ ) ₂ 339 3,5-Me ₂ 0 about H H Me t-Fropyi resin 340 3,5-Me ₂ 0 0 H H Et i-P oil i resin 341 3,5-Me ₂ 0 about H H Et chfch ₃ resin 342 3.5-(OEi) ₂ 1 about H H CH ₂ -c-Propyl i-Propyl 343 3-CF ₃ 0 with H H Me CF(CH ₃ ) ₂ 344 3-CJ 0 about H H c-Propyl chfch ₃ resin 345 3-Cl 0 about H H c-Buty i-Propyl 346 3-CI 0 about Me H Me i-Propyl resin 347 3-CI 0 about H H Et CF ₂ CHF ₂ resin 348 3-Cl,5-Me 0 about H Et CH ₂ -c-Propyl cf ₃ 349 3-Cl,5-Me 0 0 H H _CH2OMe cf ₂ chf ₂ 350 3-F 0 about H H c-Butyl cf ₂ chf ₂ 351 3-F 0 about H H Et chfch ₃ resin

• · • ··· M · ··

No. From m Y R ³ R ⁴ R ⁶ R ³ physical data 352 3-F 2 0 H H H CF(CH ₃ ) ₂ 353 3-F 0 0 H H H CF2CHF ₂ 354 3-F,5-OMe 0 0 H H cf ₃ CHFCH ₃ 355 3-Me 0 0 Me Me H CF(CH ₃ ) ₂ 356 3-Me 0 0 Me H Me i-Propyl oil 357 3-Me 0 0 Me H Me CHFCH ₃ oil 358 3-Me 0 0 H H Et i-Propyl resin 359 3-Me,4-F 0 0 H H Et CF ₂ CHF ₂ 360 3-Me,4-F 0 0 H H c-Propyl CHFCH ₃ ^resin 361 3-Me,4-F 0 0 H H c-Eutyl i-Propyl 362 3-OMe 0 0 H H c-Butyl i-Propyl 363 3-OMe 0 0 H Me n-Butyl CF ₂ CHF ₂ 364 3-OMe, 5-Cl 0 0 H H Me cf ₂ chf ₂ resin 365 3-Ph 1 0 H H c-Pentyl CHFCH ₃ 366 H 0 0 H H c-Eutyl i-Propyl resin 367 H 0 0 Me H Me CHFCH ₃ 368 ^H c 0 H H Me CF(CH ₃ ) ₂ resin 369 H 0 0 H H Et CF(CH ₃ ) ₂ resin 370 3.5-F ₂ 0 0 H H Et CF(CH ₃ ) ₂ resin 371 3-CF ₃ 0 0 H H _CH2OEt CF(CH ₃ ) ₂ 372 3-Cl 0 0 H H Et i-Propyl resin 373 3-F 0 0 H H Me CF ₂ CHF ₂ resin 374 3-Me 0 0 H H c-Butyl CHFCH3 resin 375 3-Me,4-F 0 0 H H Et i-Propyl resin 376 3-OMe 0 0 H H Et i-Propyl resin 377 H 0 0 Me Me H CF ₂ CKF ₂ 378 3.5-F ₂ 0 0 H H Et CHFCH ₃ resin 379 3-CFa 0 0 H H Me cf ₃ 380 3-Cl 0 0 H H Et CF(CH ₃ ) ₂ resin 381 3-F 0 0 H H Et i-Propyl resin 382 3-Me 0 0 H H c-Butyl CF ₂ CHF ₂ 383 3-Me,4-F 0 0 H H Et CF(CH ₃ ) ₂ resin 384 3-OMe 0 0 H H Et CF(CH ₃ ) ₂ resin 385 H 0 0 Me H Me i-Propyl

• ·

No. From m Y R ³ R ⁴ R ⁶ R ⁸ physical data 386 3,4,5-CI ₃ 0 about H H t-Butyl CF3 387 3,5-Me ₂ 0 about H H Et CF ₂ CHF ₂ resin 388 3-CI 0 about H H c-Butyl CP(CH ₃ ) ₂ resin 389 3-F 0 about H H c-Propyl i-Propyl 390 3-F,5-Me 2 about H H _CH2OEt CHFCH ₃ 391 3-Me 0 about Me H Me CF ₂ CHF ₂ 392 3-Me,4-F 0 about H H c-Butyl CF(CH ₃ ) ₂ 393 3-Ph 0 Sat ₂ H H s-Butyl CF(CH ₃ ) ₂ 394 H 0 about H H Et cf ₂ chf ₂ resin 395 4-F 0 about H H c-Butyl i-Propyl resin 396 4-F 0 about H H c-Butyl CF(CH ₃ ) ₂ resin 397 4-F 0 0 H H c-Butyl CHFCH ₃ 'resin 398 4-F 0 0 H H c-Butyl CF ₂ CHF ₂ resin 399 3,4-F ₂ 0 about H H c-Butyl i-Propyl !resin 400 3,4-F ₂ 0 about H H c-Butyl CF(CH ₃ ) ₂ resin 401 3,4-F ₂ 0 about H H c-Butyl chfch ₃ resin 402 3,4-F ₂ 0 about H H c-Butyl cf ₂ chf ₂ resin 403 To 0 about H H c-Butyl CCl( _CH3 ) ₂ resin 404 3-Me 0 about H H c-Butyl CCl( _CH3 ) ₃ resin 405 H 0 about H H c-Butyl Me resin 406 3-Me 0 about H H c-Butyl Et resin 407 H 0 about H H c-Butyl Me ‘resin 408 3-Me 0 about H H c-Butyl Et resin 409 3-Me 0 about H H c-Butyl CF ₂ CF ₃ resin 410 4-F 0 about H H c-Propyl i-Propyl resin 411 4-F 0 about H H c-Propyl CF(CH ₃ ) ₂ resin 412 4-F 0 about H H c-Propyl chfch ₃ resin 413 4-F 0 about H H c-Propyl cf ₂ chf ₂ resin 414 3,4-F ₂ 0 about H H c-Propyl i-Propyl 415 3,4-F ₂ 0 about H H c-Propyl CF(CH ₃ ) ₂ 416 3,4-F ₂ 0 about H H c-Propyl chfch ₃ 417 3,4-F ₂ 0 about H H c-Propyl cf ₂ chf ₂ 418 H 0 about H H c-Propyl CCl( _CH3 ) ₂ resin 419 3-Me 0 about H H c-Propyl CCl( _CH3 ) ₃ resin

• ·

No. 2 m Y R ³ R ⁴ R ⁶ R ⁸ Even physical data 420 The 0 0 H H c-Propyl Me ‘resin 421 3-Me 0 about H H c-Propyl Et resin 422 The 0 about H H c-Propyl Me resin 423 3-Me 0 0 H H c-Propyl Et ‘resin 424 3-Me 0 about H H c-Propyl CF ₂ CF ₃ 'resin 425 3-Me 0 0 H H Et Me * resin 426 3-Me 0 0 H H Et Et resin 427 3-Me 0 about H H Et CF ₂ CF ₃ resin 428 4-F 1 about H H Et CF(CH ₃ ) ₂ 429 4-F 1 0 H H Et chfch ₃ 430 3-CI 1 about H H Et CF(CH ₃ ) ₂ 431 3-CI 1 about H H Et chfch ₃ 432 3-Me 1 about H H Et CF(CH ₃ ) ₂ 433 3-Me 1 about H H Et chfch ₃ 434 3-Me,4-F 1 0 H H Et CF(CH ₃ ) ₂ 435 3-Me,4-F 1 about To H Et chfch ₃ 436 3,5-Me ₂ 1 0 H H Et CF(CH ₃ ) ₂ 437 3,5-Me ₂ 1 0 H H Et ckfch ₃ 438 3-F 1 0 H H Et CF(CH ₃ ) ₂ 439 3-F 1 about H H Et chfch ₃ 440 H 1 about H H Et CF(CH ₃ ) ₂ 441 H 1 about H H Et chfch ₃ 442 3-Cl,5-F 1 about H H Et CF(CH ₃ ) ₂ 443 3-C1.5-F 1 about H H Et CHFCHs 444 3-CI 2 about H H Et CF(CH ₃ ) ₂ 445 3-CI 2 0 H H Et CHFCH ₃ 446 3-Me 2 about H H Et CF(CH ₃ ) ₂ 447 3-Me 2 about H H Et chfch ₃ 448 3-Me,4-F 2 about H H Et CF(CH ₃ ) ₂ 449 3-Me,4-F 2 about H H Et chfch ₃ 450 3,5-Me ₂ 2 about H H Et CF(CH ₃ ) ₂ 451 3,5-Me ₂ 2 about H H Et chfch ₃ 452 3-F 2 0 H H Et CF(CH ₃ ) ₂ 453 3-F 2 about H H Et chfch ₃

• · • · •Q? ·• ·-· · · · · ·

No. From m Y R ³ R ⁴ R ⁶ R ⁸ physical data 454 H 2 0 H H Et CF(CH ₃ ) ₂ 455 H 2 about H H Et CHFCH ₃ 456 3-CI 0 about Et Et H CF(CH ₃ ) ₂ resin 457 3-CI 0 0 Et Et H chfch ₃ resin 458 3-Me 0 about H H Me Me resin 459 3-Me 0 about H H Me Et 'resin 460 3-Me 0 about H H Me cf ₂ cf ₃ resin 461 4-F 1 about H H Me CF(CH ₃ ) ₂ 462 4-F 1 about H H Me CHFCH ₃ 463 3-CI 1 0 H H Me CF(CH ₃ ) ₂ 464 3-CI 1 about H H Me CHFCH ₃ 465 3-Me 1 about H H Me CF(CH ₃ ) ₂ 466 3-Me 1 about H H Me chfch ₃ 467 3-Me,4-F 1 about H H Me CF(CH ₃ ) ₂ 468 3-Me,4-F 1 about H H Me chfch ₃ 469 3,5-Me ₂ 1 about H H Me CF(CH ₃ ) ₂ 470 3,5-Me ₂ 1 about H H Me chfch ₃ 471 3-F 1 0 H H Me CF(CH ₃ ) ₂ 472 3-F 1 about H H Me CHFCH ₃ 473 H 1 about H H Me CF(CH ₃ ) ₂ 474 H 1 0 H H Me chfch ₃ 475 3-CI.5-F 1 0 H H Me CF(CH ₃ ) ₂ 476 3-CI.5-F 1 about H H Me chfch ₃ 477 3-CI 2 about H H Me CF(CH ₃ ) ₂ 478 3-CI 2 about H H Me CHFCH ₃ 479 3-Me 2 about H H Me CF(CH ₃ ) ₂ 480 3-Me 2 about H H Me chfch ₃ 481 3-Me,4-F 2 about H H Me CF(CH ₃ ) ₂ 482 3-Me,4-F 2 about H H Me chfch ₃ 483 3,5-Me ₂ 2 about H H Me CF(CH ₃ ) ₂ 484 3,5-Me ₂ 2 about H H Me chfch ₃ 485 3-F 2 0 H H Me CF(CH ₃ ) ₂ 486 .. 3-F 2 about H H Me chfch ₃ 487 H 2 about H H Me CF(CH ₃ ) ₂

No. From m Y R ³ R ⁴ R ⁶ R ⁸ physical data 488 H 2 0 H H Me chfch ₃

Table 3

Compounds of general formula Ic (= formula I , where n = 3 , R ¹ , R^ R$, R^, R^ and R^O - hydrogen atom and Aryl = substituted phenyl according to the table)

No. From m Y R ³ R ⁴ R ⁶ R ⁸ physical data 489 3-F 0 0 H H Me chfch ₃ 490 H 0 about H H Et CF(CH ₃ ) ₂ resin 491 3-Me 0 0 H Me c-Propyl i-Propyi 492 3-CI 0 0 H H c-Propyl CF ₂ CHF ₂ 493 3-F 0 about H H c-Eutyi chfch ₃ 494 3,5-Me ₂ 0 0 H H t-Butyl i-Propyl 495 3-Cl,5-Me 2 Sat ₂ H H Me chfcf ₃ 496 3-F,5-Me 0 about H H CK ₂ F CF(CH ₃ ) ₂ 497 H 0 about H H Et cf ₂ chf ₂ 498 3-F 0 about H H c-Propyl CF(CH ₃ )2 499 3,5-Me ₂ 0 about H H _CH2F CHFCK ₃ 500 3-F,5-OMe 0 about H H CHrC-Butyl i-Propyl 501 H 0 about H H Me CF(CH ₃ ) ₂ resin 502 3-Me 0 about H H Me CF(CH ₃ ) ₂ resin 503 3-Me 0 0 H H Et cf ₂ chf ₂ 504 3-CI 0 about H H Et cf ₂ chf ₂ 505 H 0 0 H H c-Butyl CF(CH ₃ ) ₂ 506 3-Me 0 0 H H c-Butyl CF(CH ₃ ) ₂

• ·

No. From m Y R ³ R ⁴ R ^S R ⁸ physical data 507 3,5-(OMe) ₂ 1 with H Et H CF(CH ₃ ) ₂ 508 3.5-F ₂ 0 0 H H c-Pentyl chfch ₃ 509 3-CF ₃ 2 with H H i-Propyl i-Propyl 510 H 0 0 H H Hey i-Propyl [resin 511 3-Cl 0 0 H H H chfch ₃ 512 3,5-Me ₂ 0 0 H H s-Butyl chfcf ₃ 513 3-F,5-Me 1 0 H H CF ₃ chfch ₃ 514 3-Me 0 0 H H Et CF(CH ₃ ) ₂ resin 515 3-F 0 0 H H c-Propyl cf ₂ chf ₂ 516 3,5-(OMe) ₂ 1 C(O)O H Et CH ₂ -c-8-butyl cf ₃ 517 3-F,5-OMe 0 0 H H _CH2OEt CHFCH, 518 H 0 0 H H Me CHFCH ₃ 'resin 519 3-Me 0 0 H H Me CF2CHF2 520 3-CI 0 0 H H Et i-Propyl 521 3-F 0 0 H To Et CF(CH ₃ ) ₂ 522 H 0 0 H H c-Eutyl chfch ₃ 523 3-Me 0 0 H H H cf ₂ chf ₂ 524 3.5-F ₂ 1 0 H Me Me cf ₃ 525 3-OMe,5-CI 0 0 H H t-Butyl i-Propyi 526 3-CFa 0 0 H H n-Buty cf ₂ chf ₂ 527 3-Cl 0 0 H H Me cf ₂ chf ₂ 528 H 0 ^{0 H} H c-Propyl Cr(CH ₃ ) ₂ resin 529 3-Cl 0 0 H H c-Butyl CF ₂ CHF ₂ 530 3-OEi 1 0 ^{H H} CHrC-Butyl i-Propyl 531 H 0 0 ^{H H} Me i-Propyl 'resin 532 3-Me 0 0 H H Me chfch ₃ resin 533 3-F 0 0 H H H CF(CH ₃ ) ₂ 534 3-Me,4-F 0 0 H H Me cf ₂ chf ₂ 535 3-Me 0 0 H H Et chfch ₃ resin 536 3-F 0 0 H H Et i-Propyl 537 H 0 0 H H c-Propyl CF ₂ CHF ₂ 538 3-Cl 0 0 H H c-Propyl CF(CH3) ₂ 539 H 0 0 H H c-Butyl i-Propyl 540 3-Me 0 0 H H c-Butyl chfch ₃

No. From m Y R ³ R ⁴ R ^S R ⁸ physical data 541 3-F 0 0 H H c-Butyl CF(CH ₃ ) ₂ 542 3-OMe 0 with H H c-Pentyl CHFCH3 543 3,5-(OMe) ₂ 0 0 H H _CH2OMe CHFCH3 544 3-OMe, 5-Cl 0 with H H s-Butyl CF(CH ₃ ) ₂ 545 3-OEt 0 0 H H _CH2OEt CHFCH3 546 3-F,5-Me 0 with H H t-Butyl cf ₃ 547 3-CF ₃ 0 0 H H Me CF(CH ₃ ) ₂ 548 3-Me,4-F 0 0 H H Me CF(CH ₃ ) ₂ 549 3-Me 0 0 H H c-Propyl cf ₂ chf ₂ 550 3-OMe 0 C(0)0 H H i-Propyl i-Propyl 551 3-Cl,5-Me 0 0 H H c-Pentyl chfch ₃ 552 3-Cl 0 0 H H Me CHFCH3 553 3-Me 0 0 H H Et i-Propyl resin 554 H 0 0 H H c-Propyl i-Propyl resin 555 3-F 0 0 H H c-Propyl CHFCH ₃ 556 3-Cl 0 0 H Me c-Butyl CHFCH ₃ 557 3,5-(OMe) ₂ 0 0 H H CH ₂ -c-Propyl CF(CH ₃ ) ₂ 558 3-OEt 0 0 H H CH ₂ -c-Propyl cf ₃ 559 3-F,5-OMe 0 Sat ₂ H H _CH2OMe CF ₂ CHF ₂ 560 3-Cl 0 0 H H Me CF(CH ₃ ) ₂ 561 3-F 0 0 H Et H cf ₂ chf ₂ 562 3-Cl 0 0 H H c-Butyl CF(CH ₃ ) ₂ 563 3-OMe,5-Cl 0 0 H H _CH2F i-Propyl 564 3-Cl 0 0 H H Me i-Propyi 565 3-F 0 0 H H Et chfch ₃ 566 3-Cl 0 0 H H c-Butyl i-Propyl 567 3-OMe,5-CI 0 0 H Me CF ₃ CF ₂ CHF ₂ 568 H 0 0 H H Et chfch ₃ resin 569 3-F 0 0 H H c-Propyl i-Propyl 570 3,5-Me ₂ 0 0 H H cf ₃ CF ₂ CHF ₂ 571 3-F,5-OMe 0 0 H H CH ₂ -c-Propyl CF3 572 3-F 0 0 H H Me i-Propyl 573 H 0 0 H H c-Propyl CHFCH ₃ resin 574 3-F 0 0 H H H i-Propyi

No. From m Y R ³ R ⁴ R ^S R ⁸ physical data 575 3-OEt 0 about H H H cf ₂ chf ₂ 576 3-Me,4-F 0 about H H H i-Propyl 577 3-Me 0 about H H c-Propyl chfch ₃ resin 578 3-OMe 0 about H Me Me cf ₃ 579 3-Cl,5-Me 0 about H H n-Butyl cf ₂ chf ₂ 580 3-F 0 about H H Me cf ₂ chf ₂ 581 3-Me,4-F 0 about H H Me CHFCH ₃ 582 3-Me 0 about H H c-Propyl CF(CH ₃ ) ₂ resin 583 3-CI 0 about H H c-Propyl i-Propyi 584 3-F 0 about H H c-Butyl CF ₂ CHF ₂ 585 3-OMe 1 about H H n-Butyl CF ₂ CHF ₂ 586 3-Cl,5-Me 0 about To H i-Propyl i-Propyl 587 3-F,5-Me 0 about H Et H CF(CH ₃ ) ₂ 588 H 0 about H H Me cf ₂ chf ₂ resin 589 3-CI 0 about H H Et CF(CH3) ₂ 590 H 0 about H H c-Butyl cf ₂ chf ₂ 591 3.5-F ₂ 0 with H H i-Propyl i-Propyl 592 3-CF ₃ 0 Sat ₂ H H c-Pentyl cf ₃ 593 3-Me 0 about H H Me i-Propyl resin 594 3-CI 0 about H H Et chfch ₃ 595 3-Me 0 about H H c-Butyl i-Propyl resin 59c 3.5-F ₂ 0 about H H n-Ethyl CF ₂ CHF ₂

» ·

Table 4

Compounds of general formula Id (= formula I , where n = 4 , R , R ² , R ⁵ , R ⁷ , R ⁹ and R ¹⁰ = hydrogen atom and Aryl = substituted phenyl according to the table)

R ⁶ (CH ₂ ) _m -Y-(CH ₂ ) ₃ -CR ³ R ⁴ -CH-NH

(Id)

No. From m Y R ³ R ⁴ R ⁸ R ⁸ physics, data 537 3-F 0 about H H Me chfch ₃ 598 H 0 about H H Et CF(CH ₃ ) ₂ oil 5SS 3-Me 0 about H Me c-Propyl i-Propyl 600 3-CI 0 0 H H c-Propyl CF ₂ CHF ₂ 601 3-F 0 about H H c-Eutyl chfch ₃ 602 3,5-Me ₂ 0 about H H t-Eutyl i-Propyl 603 3-Cl,5-Me 2 Sat ₂ H H Me chfcf ₃ 604 3-F,5-Me 0 about H H _CH2F CF(CH ₃ ) ₂ 605 H 0 about H H Et cf ₂ ckf ₂ oil 606 3-F 0 about H H c-Propyl CF(CH ₃ ) ₂ 607 3,5-Me ₂ C 0 H H CK ₂ F chfch ₃ 608 3-F,5-OMe C about H H _CH2 -c-Butyl i-Propyi 609 H 0 about H H Me CF(CH ₃ ) ₂ oil 610 3-Me 0 0 H H Me CF(CH ₃ ) ₂ 611 3-Me 0 about H H Et cf ₂ chf ₂ 612 3-CI 0 about H H Et cf ₂ chf ₂ 613 H 0 about H H c-Butyl CF(CH ₃ ) ₂ 614 3-Me 0 about H H c-Butyl CF(CH ₃ ) ₂ 615 3,5-(OMe) ₂ 1 with H Et H CF(CH ₃ ) ₂ 616 3.5-F 0 0 H H c-Pentyl chfch ₃ 617 3-CF ₃ 2 with H H i-Propyl i-Propyi 618 H 0 about H H Et i-Propyl oil 619 3-CI 0 about H H H chfch ₃ 620 3,5-Me ₂ 0 about H H s-Butyl chfcf ₃

• ♦ * * • ·

AND

No. From m Y R ³ R ⁴ R ⁸ R ⁸ physical data 621 3-F,5-Me 1 about H H cf ₃ chfch ₃ 622 3-Me 0 about H H Et CF(CH ₃ ) ₂ 623 3-F 0 about H H c-Propyl cf ₂ chf ₂ 624 3,5-(OMe) ₂ 1 C(O)O H Et _CH2 -c-Butyl cf ₃ 625 3-F,5-OMe 0 about H H _CH2OEt CHFCH ₃ 626 ' H 0 about H H Me chfch ₃ lol 627 3-Me 0 about H H Me cf ₂ chf ₂ 628 3-CI 0 about H H Et i-Propyl 629 3-F 0 about H H Et CF(CH ₃ ) ₂ 630 H 0 about H H c-Butyl chfch ₃ 631 3-Me 0 about H H H cf ₂ chf ₂ 632 3.5-F ₂ 1 about H Me Me cf ₃ 633 3-OMe,5-CI 0 about H H t-Butyl i-Propyl 634 3-CF ₃ 0 about H H n-Butyl cf ₂ chf ₂ 635 3-CI 0 about H H Me cf ₂ chf ₂ 636 H 0 about H H c-Propyl CF(CH ₃ ) ₂ oil 637 3-CI 0 about H H c-Butyl cf ₂ chf ₂ 638 3-OEt 1 0 H H _CH2 -c-Butyl i-Propyl 639 H 0 about H H Me i-Propyl oil 640 3-Me 0 about H H Me CHFCH ₃ 641 3-F 0 about H H H CF(CH ₃ ) ₂ £42 3-Me,4-F 0 about H H Me cf ₂ chf ₂ 643 3-Me 1 about H H Et ckfch ₃ 644 3-F 0 0 H H Et i-Propyl 645 H 0 about H H c-Propyl cf ₂ chf ₂ oil 646 3-CI 0 about H H c-Propyl CF(CH ₃ ) ₂ 647 H 0 about H H c-Butyl i-Propyl 648 3-Me 0 about H H c-Butyl chfch ₃ 649 3-F 1 about H H c-Butyl CF(CH ₃ ) ₂ 650 3-OMe 0 with H H c-Pentyl chfch ₃ 651 3,5-OMe 0 about H H _CH20Me CHFCH ₃ 652 3-OMe,5-CI 0 with H H s-Butyl CF(CH ₃ ) ₂ 653 3-OEt 0 about H H _CH2OEt CHFCH ₃ 654 3-F,5-Me 0 with H H t-Butyl cf ₃

• · · • ·

No. From m Y R ³ R ⁴ R ⁶ R ⁸ physical data 655 3-CF ₃ 0 0 H H Me CF(CH ₃ ) ₂ 656 3-Me,4-F 1 0 H H Me CF(CH ₃ ) ₂ 657 3-Me . 0 0 H H c-Propyl cf ₂ chf ₂ 658 3-OMe 0 C(O)O H H i-Propyl i-Propyl 659 3-Cl,5-Me 0 0 H H c-Pentyl CHFCH3 660 3-CI 0 0 H H Me chfch ₃ 661 3-Me 0 0 H H Et i-Propyl 662 H 1 0 H H c-Propyl i-Propyl 663 3-F 0 0 H H c-Propyl CHFCH ₃ 664 3-CI 0 0 H Me c-Butyl chfch ₃ 665 3,5-(OMe) ₂ 0 0 H H CH ₂ -c-Propyl CF(CH ₃ ) ₂ 666 3-OEt 0 0 H H CH ₂ -c-Propyl cf ₃ 667 3-F,5-OMe 0 SO2 H H _CH2OMe cf ₂ chf ₂ 668 3-CI 0 About H H Me CF(CH ₃ ) ₂ 669 3-F 0 About H Et H cf ₂ chf ₂ 670 3-CI 0 0 H H c-Butyl CF(CH ₃ ) ₂ 671 3-OMe,5-CI 0 About H H _CH2F i-Propyl 672 3-CI 0 About H H Me i-Propyl 673 3-F 0 About H H Et chfch ₃ 674 3-CI 0 0 H H c-Butyl i-Propyl 675 3-OMe,5-CI 0 0 H Me CF ₃ CF ₂ CHF ₂ 676 H 1 0 H H Et chfch ₃ 677 3-F 0 0 H H c-Propyl i-Propyi 678 3,5-Me ₂ 0 0 H H cf ₃ cf ₂ chf ₂ 679 3-F,5-OMe 0 0 H H CH ₂ -c-Propyl cf ₃ 680 3-F 0 0 H H Me i-Propyl 681 H 0 0 H H c-Propyl CHFCH ₃ oil 682 3-F 0 0 H H H i-Propyl 683 3-OEt 0 0 H H H CF ₂ CHF ₂ 684 3-Me,4-F 0 0 H H H i-Propyl 685 3-Me 0 0 H H c-Propyl CHFCH ₃ 686 3-OMe 0 0 H Me Me cf ₃ 687 3-Cl,5-Me 0 0 H H n-Butyl cf ₂ chf ₂ 688 3-F 0 0 H H Me CF2CHF2

100

No. From m Y R ³ R ⁴ R ^S R ⁸ physical data 689 3-Me,4-F 0 about H H Me chfch ₃ 690 3-Me 0 about H H c-Fropyl CF(CH ₃ ) ₂ 691 3-CI 0 about H H c-Propyl i-Propyl 692 3-F 0 about H H c-Butyl CF ₂ CHF ₂ 693 3-OMe 1 about H H n-Eutyi cf ₂ chf ₂ 694 3-Cl,5-Me 0 about H H i-Propyl i-Propyl 695 3-F,5-Me 0 about H Et H CF(CH ₃ ) ₂ 696 H 0 about H H Me cf ₂ chf ₂ oil 697 3-CI 0 about H H Et CF(CH ₃ ) ₂ 698 H 0 about To H c-Eutyi cf ₂ chf ₂ oil 699 3.5-F 1 with H H i-Propyl i-Propyl 700 3-CF ₃ 0 Sat ₂ H H c-Pentyl cf ₃ 701 3-Me 0 about H H Me i-Propyi 702 3-CI 0 about H H Et chfch ₃ 703 3-Me 0 about H H c-Butyl i-Propyl 704 3.5-F ₂ ⁰ about H H n-Butyl CF ₂ CHF ₂

• ·

- 101

Table 5

Compounds of general formula Id (= formula I , where n = 5 , R , R ² , R ⁵ , R ⁷ , R ⁹ and R ¹⁰ = hydrogen atom and Aryl = substituted phenyl according to the table)

R ⁸

No. From m Y R ³ R ⁴ R ⁶ R ⁸ 705 3-F 0 0 H H Me CHFCH3 706 H 0 0 H H Et CF(CH ₃ ) ₂ 707 3-Me 0 0 H Me c-Propyl i-Propyl 708 3-CI 0 0 H H c-Propyl CF ₂ CHF ₂ 70S 3-F 0 0 H H c-Butyl CHFCH ₃ 710 3,5-Me ₂ 0 0 H H t-Eutyl i-Propyi 711 3-Cl,5-Me 2 Sat ₂ H H Me CHFCF ₃ 712 3-F,5-Me 0 0 H H _CH2F CF(CH ₃ ) ₂ 713 H 0 0 H H Et cf ₂ chf ₂ 714 3-F 0 0 H H c-Propyl CF(CH ₃ ) ₂ 715 3,5-Me ₂ 0 0 H H _CH2F CHFCH ₃ 716 3-F,5-OMe 0 0 H H CH2 _- cButyl i-Fropyl 717 H 0 0 H H Me CF(CH ₃ ) ₂ 718 3-Me 0 0 H H Me CF(CH ₃ ) ₂ 719 3-Me 0 0 H H Et cf ₂ chf ₂ 720 3-CI 0 0 H H Et cf ₂ chf ₂ 721 H 0 0 H H c-Butyl CF(CH ₃ ) ₂ 722 3-Me 0 0 H H c-Butyl CF(CH ₃ ) ₂ 723 3,5-(OMe) ₂ 1 with H Et H CF(CH ₃ ) ₂ 724 3.5-F ₂ 0 0 H H c-Pentyl CHFCH3 ⁷²⁵ 3-CF ₃ 2 with H H i-Propyl i-Propyl 726 H 0 0 H H Et i-Propyl 727 3-CI 0 0 H H H CHFCH3

102

No. From m Y R ³ R ⁴ R ⁸ R ⁸ physical data 728 3.5-Mβ2 0 about H H s-Butyl CHFCF ₃ 729 3-F,5-Me 1 about H H cf ₃ CHFCH ₃ 730 3-Me 0 about H H Et CF(CH ₃ ) ₂ 731 3-F 0 about H H c-Propyl cf ₂ chf ₂ 732 3,5-(OMe) ₂ 1 C(O)O H Et _CH2 -c-Butyl cf ₃ 733 3-F,5-OMe 0 about H H _CH2OEt CHFCH ₃ 734 H 0 0 H H Me CHFCH ₃ 735 3-Me 0 about H H Me CF ₂ CHF ₂ 736 3-CI 0 about H H Et i-Propyl 737 3-F 0 0 H H Et CF(CH ₃ ) ₂ 738 H 0 about H H c-Butyl chfch ₃ 739 3-Me 0 about H H H cf ₂ ckf ₂ 740 3.5-F ₂ 1 about H Me Me cf ₃ 741 3-OMe,5-CI 0 about H H t-Butyl i-Propyl 742 3-CF ₃ 0 about H H n-Butyl CF ₂ CHF ₂ 743 3-CI 0 0 H H Me cf ₂ chf ₂ 744 To 0 about H H c-Propyl CF(CH ₃ ) ₂ 745 3-CI 0 0 H H c-Butyl cf ₂ chf ₂ 746 3-OEt 1 about H H _CH2 -c-Butyl i-Propyl 747 H 0 about H H Me i-Propyl 748 3-Me 0 about H H Me CHFCH ₃ 749 3-F 0 about H H H CF(CH ₃ ) ₂ 750 3-Me,4-F 0 about H H Me cf ₂ chf ₂ 751 3-Me 1 about H H Et CHFCH ₃ 752 3-F 0 about H H Et i-Propyl 753 H 0 about H H c-Propyl CF ₂ CHF ₂ 754 3-CI 0 about H H c-Propyl CF(CH ₃ ) ₂ 755 H 0 about H H c-Butyl i-Propyl 756 3-Me 0 about H H c-Butyl CHFCH ₃ 757 3-F 1 about H H c-Butyl CF(CH ₃ ) ₂ 758 3-OMe 0 with H H c-Pentyl chfch ₃ 759 3,5-(OMe) ₂ 0 0 H H _CH2OMe CHFCH ₃ 760 3-OMe,5-CI 0 with H H s-Butyl CF(CH ₃ ) ₂ 761 3-OEt 0 about H H _CH2OEt chfch ₃

• ·

- 103

No. From m Y R ³ R ⁴ R ⁶ R ⁸ physical data 762 3-F,5-Me 0 with H H t-Butyl cf ₃ 763 3-CF ₃ 0 0 H H Me CF(CH ₃ ) ₂ 764 3-Me,4-F 1 about H H Me CF(CH ₃ ) ₂ 765 3-Me 0 about H H c-Propyl cf ₂ chf ₂ 766 3-OMe 0 C(O)O H H i-Propyl i-Propyl 767 3-Cl,5-Me 0 about H H c-Pentyl chfch ₃ 768 3-Cl 0 about H H Me chfch ₃ 769 3-Me 0 about H H Et i-Propyl 770 H 1 0 H H c-Propyl i-Propyl 771 3-F 0 0 H H c-Propyl CHFCHa 772 3-CI 0 about H Me c-Butyl chfch ₃ 773 3,5-(OMe) ₂ 0 about H H CH ₂ -c-Propyl CF(CH ₃ ) ₂ 774 3-OEt 0 about H H CH ₂ -c-Propyl cf ₃ 775 3-F,5-OMe 0 Sat ₂ H H _CH2OMe cf ₂ chf ₂ 776 3-CI 0 about H H Me CF(CH ₃ ) ₂ 777 3-F 0 0 H Et H cf ₂ chf ₂ 778 3-CI 0 about H H c-Butyl CF(CH ₃ ) ₂ 779 3-OMe, 5-Ci 0 about H H _CH2F i-Propyi 780 3-CI 0 0 H H Me i-Props! 781 3-F 0 0 H H Et chfch ₃ 782 3-CI 0 about H H c-Butyl i-Propyi 783 3-OMe, 5-CI 0 about H Me cf ₃ CF ₂ CHF ₂ 784 H 1 about H H Et chfch ₃ 785 3-F 0 0 H H c-Propyl i-Propyl 786 3,5-Me ₂ 0 about H H cf ₃ CF ₂ CHF ₂ 787 3-F,5-OMe 0 about H H CH ₂ -c-Propyl cf ₃ 788 3-F 0 about H H Me i-Propyl 789 H 0 about H H c-Propyl chfch ₃ 790 3-F 0 about H H H i-Propyl 791 3-OEt 0 0 H H H CF ₂ CHF ₂ 792 3-Me,4-F 0 about H H H i-Propyl 793 3-Me 0 about H H c-Propyl CHFCH ₃ 794 3-OMe 0 about H Me Me cf ₃ 795 3-Cl,5-Me 0 about H H n-Butyl cf ₂ chf ₂

• ·

104

No. From m Y R ³ R ⁴ R ^fi R ⁸ physical data 796 3-F 0 about H H Me cf ₂ chf ₂ 797 3-Me,4-F 0 about H H Me chfch ₃ 798 3-Me 0 about H H c-Propyl CF(CH ₃ ) ₂ 799 3-CI 0 about H H c-Propyl i-Propyl 800 3-F 0 about H H c-Butyl CF ₂ CHF ₂ 801 3-OMe 1 about H H n-Butyl cf ₂ chf ₂ 802 3-Cl,5-Me 0 about H H i-Propyl i-Propyl 803 3-F,5-Me 0 about H Et H CF(CH ₃ ) ₂ 804 H 0 about H H Me cf ₂ chf ₂ 805 3-CI 0 0 H H Et CF(CH ₃ ) ₂ 806 H 0 about H H c-Butyl cf ₂ chf ₂ 807 3.5-F ₂ 1 with H H i-Propyl i-Propyl 808 3-CF ₃ 0 Sat ₂ H H c-Pentyl cf ₃ 809 3-Me 0 about H H Me i-Propyl 810 3-CI 0 about H H Et chfch ₃ 811 3-Me 0 about H H c-Butyl i-Propyl 812 3.5-F ₂ 0 about H H n-Butyl CF ₂ CHF ₂

105

Table 6

Compounds of general formula If (= formula I , where m — 0 , Y 0, (CR ³ R ⁴ ) _n -CR ⁵ R ⁶ = cyclohexane-1,3-diyl, R^, R^ = hydrogen atom and Aryl = substituted phenyl according to the table)

1No. From R ⁸ physical data 813 3,4-F ₂ i-Propyl 814 3,4-F ₂ CF(CH ₃ ) ₂ 815 3,4-F ₂ CHFCH ₃ 816 3,4-F ₂ CF ₂ CHF ₂ 817 3,5-Me ₂ CF(CH ₃ ) ₂ 818 3,5-Me ₂ CHFCH ₃ 819 3,5-Me ₂ CF(CH ₃ ) ₂ 820 3,5-Me ₂ CHFCH ₃ 821 3-Cl CF(CH ₃ ) ₂ 822 3-Cl chfch ₃ 823 3-CI.5-F CF(CH ₃ ) ₂ 824 3-CJ.5-F chfch ₃ 825 3-F CF(CH3) ₂ 826 3-F CHFCH ₃ 827 3-Me CCl(CH ₃ ) ₃ 828 3-Me Et 829 3-Me CF ₂ CF ₃ 830 3-Me CF(CH ₃ ) ₂ 831 3-Me chfch ₃ 832 3-Me,4-F CF(CH ₃ ) ₂ 833 3-Me,4-F CHFCH ₃

• · • ·

- 106 -

No. From R ⁸ physical data 834 4-F i-Propyl 835 4-F CF(CH ₃ ) ₂ 836 4-F CHFCH ₃ 837 4-F CF ₂ CHF ₂ 838 H CCl( _CH3 ) ₂ 839 H Me 840 H CF(CH ₃ ) ₂ 841 H chfch ₃

Table 7

Compounds of general formula Ig (= formula I , where m = 0 , Y = 0, (CR ³ R ⁴ )n-CR ⁵ R ⁶ - -CH2-1,2-cycloC ₆ H ₁₀ -, R ⁷ , R ⁹ ,R ¹⁰ = hydrogen atom and Aryl = substituted phenyl according to the table)

No. From R8 ' physical data 842 3.4-F ₂ i-Propyl 843 3,4-F ₂ CF(CH ₃ ) ₂ 844 3,4-F ₂ chfch ₃ 845 3,4-F ₂ cf ₂ chf ₂ 846 3,5-Me ₂ CF(CH ₃ ) ₂ 847 3.5-Mβ2 chfch ₃ 848 3,5-Me ₂ CF(CH ₃ ) ₂ 849 3,5-Me ₂ chfch ₃ 850 3-Cl CF(CH ₃ ) ₂ 851 3-Cl chfch ₃

• ·

- 107

No. From R8 physical data 852 3-CI.5-F CF(CH ₃ ) ₂ 853 3-CI.5-F chfch ₃ 854 3-F CF(CH ₃ ) ₂ 855 3-F chfch ₃ 856 3-Me CCl( _CH3 ) ₃ 857 3-Me Et 858 3-Me cf ₂ cf ₃ 859 3-Me CF(CH ₃ ) ₂ 860 3-Me CHFCH ₃ 861 3-Me,4-F CF(CH ₃ ) ₂ 862 3-Me,4-F CHFCH ₃ 863 4-F i-Propyl 864 4-F CF(CH ₃ ) ₂ 865 4-F CHFCH ₃ 866 4-F CF ₂ CHF ₂ 867 H CCl(CH ₃ ) ₂ 868 H Me 869 H CF(CH ₃ ) ₂ resin 870 H chfch ₃ resin

• ·

108

Table 8

Compounds of general formula Ih (= formula I , where m - 0 , Y 0, (CR ³ R ⁴ )n-CR ⁵ R ⁶ = -CH2-1,2-cyclopentenyl-, R ⁷ , R ⁹ ,R ¹⁰ = hydrogen atom and Aryl = substituted phenyl according to the table)

R8

No. From R8 physical data 871 3,4-F ₂ i-Propyl 872 3,4-F ₂ CF(CH ₃ ) ₂ 873 3,4-F ₂ CHFCH ₃ 874 3,4-F ₂ CF ₂ CHF ₂ 875 3,5-Me ₂ CF(CH ₃ ) ₂ 876 3,5-Me ₂ chfch ₃ 877 3,5-Me ₂ CF(CH ₃ ) ₂ 878 3.5-year-old ₂ CHFCH ₃ 879 3-CI CF(CH ₃ ) ₂ 880 3-CI chfch ₃ 881 3-CI.5-F CF(CH3) ₂ 882 3-Cl,5-F CHFCH ₃ 883 3-F CF(CH ₃ ) ₂ 884 3-F chfch ₃ 885 3-Me CCl( _CH3 ) ₃ 886 3-Me Hey 887 3-Me cf ₂ cf ₃ 888 3-Me CF(CH ₃ ) ₂ 889 3-Me chfch ₃ 890 3-Me,4-F CF(CH ₃ ) ₂ 891 3-Me,4-F CHFCH ₃ 892 4-F i-Propyl 893 4-F CF(CH ₃ ) ₂

109

No. From R8 physical data 894 4-F chfch ₃ 895 4-F cf ₂ chf ₂ 896 H CCl( _CH3 ) ₂ 897 H Me 898 H CF(CH ₃ ) ₂ 899 H chfch ₃

Table 9

Compounds of general formula Ik (= formula I , where m — 1 , n 1, (CR ³ R ⁴ ) = carbonyl, R ¹ ,R ² ,R ⁵ ,R ⁷ ,R ⁹ ,R ¹⁰ = hydrogen atom and Aryl = substituted phenyl according to the table)

No. From Y R ^S R ³ 'physical data 900 3-F 0 Me CHFCH ₃ 901 H about Et CF(CH ₃ ) ₂ 902 3-Me about c-Propyl i-Propyl 903 3-CI 0 ch ₂ ch ₂ sch ₃ CF ₂ CHF ₂ 904 3-F N c-Butyl chfch ₃ 905 3,5-Me ₂ N t-Butyl i-Propyl 906 3-Cl,5-Me N Me chfcf ₃ 907 3-F,5-Me About Benzyl CF(CH ₃ ) ₂ 908 H N Et cf ₂ chf ₂ 909 3-F 0 c-Propyl CF(CH ₃ ) ₂ 910 3,5-Me ₂ N _CH2F CHFCH ₃ 911 3,5-Me ₂ N s-Butyl chfch ₃ 912 3-F,5-OMe 0 CHrC-Butyl i-Propyl

• ·

- 110

No. From Y R ⁶ R ⁸ physical data 913 H N Me CF(CH ₃ ) ₂ 914 3-Me About CH2CH2SCH3 CF(CH ₃ ) ₂ 915 3-Me N Et cf ₂ chf ₂ 916 3-Cl 0 Et cf ₂ chf ₂ 917 H About c-Butyl CF(CH ₃ ) ₂ 918 3-Me About c-Butyl CF(CH ₃ ) ₂ 919 H N Et Me 920 3.5-F ₂ 0 c-Pentyl CHFCH ₃ 921 3-CF ₃ 0 i-Propyl i-Propyl 922 H N Et i-Propyl 923 3-Cl 0 Benzyl CHFCH ₃ 924 H 0 CH ₂ CH ₂ SCH ₃ Me 925 3-F,5-Me About cf ₃ chfch ₃ 926 3-Me N Me CF(CH ₃ ) ₂ mp98’C 927 3-F N c-Propyl cf ₂ chf ₂ 928 2 5-(OMe) ₂ N _CH2 -c-Butyl cf ₃ 929 3-F,5-OMe N _CH2OEt CHFCH ₃ 930 H N H chfch ₃ mp123°C 931 3-Me N Me cf ₂ chf ₂ 932 3-Cl N Et i-Propyl 933 3-F N Et CF(CH ₃ ) ₂ 934 H N Et Et 935 3-Me N Benzyl cf ₂ chf ₂ 936 3.5-F ₂ N Me cf ₃ 937 3-OMe, 5-CI 0 t-Butyi i-Propyl 938 3-CFa About i-Butyl cf ₂ chf ₂ 939 3-CJ About Me cf ₂ chf ₂ 940 H About c-Propyl CF(CH ₃ ) ₂ 941 3-CJ 0 c-Butyl cf ₂ chf ₂ 942 3-OEt N CHrC-Butyl i-Propyl 943 H N Me i-Propyl 944 3-Me N Me chfch ₃ 945 3-F N H CF(CH ₃ ) ₂ 946 3-Me,4-F N Me cf ₂ chf ₂ 947 3-Me N Et chfch ₃

• · ·

111 • Φ ·* • · · · • · ·· ·· • · » · • · · · • · · · · • · · · • · · ·

No. From Y R ⁶ R ⁸ physical data 948 3-F N Et i-Propyl 949 H N c-Propyl CF ₂ CHF ₂ 950 3-Cl N c-Propyl CF(CH ₃ ) ₂ 951 H N s-Butyl Me 952 3-Me N c-Butyl CHFCH ₃ 953 3-F N c-Butyl CF(CH ₃ ) ₂ 954 3-OMe N c-Pentyl CHFCH3 955 3,5-(OMe) ₂ N _CH2OMe CHFCH3 956 3-OMe,5-Cl N CH ₂ CH ₂ SCH ₃ CF(CH ₃ ) ₂ 957 3-OEt N _CH2OEt CHFCH3 958 3-F,5-Me N t-Butyl CF ₃ 959 3-CF ₃ N Me CF(CH ₃ ) ₂ 960 3-Me,4-F N Me CF(CH ₃ ) ₂ 961 3-Me N c-Propyl cf ₂ chf ₂ 962 3-OMe N Benzyl i-Propyl 963 3-Cl,5-Me 0 c-Pentyl CHFCH ₃ 964 3-Ci About Me CKFCH ₃ 965 3-Me About Et i-Propyl 966 H About c-Propyl i-Propyl 967 3-F N c-Propyl CHFCH3 968 3-Cl N c-Butyl CHFCH ₃ 969 3,5-(OMe) ₂ N CH ₂ -cPropyl CF(CH ₃ ) ₂ 970 3-OEt N i-Butyl cf ₃ 971 3-F,5-OMe N _CH2OMe cf ₂ chf ₂ 972 3-Cl N Me CF(CH ₃ ) ₂ 973 3-F N H cf ₂ chf ₂ 974 3-Cl N c-Butyl CF(CH ₃ ) ₂ 975 3-OMe,5-Cl N _CH2F i-Propyl 976 3-Cl N Me i-Propyi 977 3-F N CH ₂ CH ₂ SCH ₃ chfch ₃ 978 3-Cl N c-Butyl i-Propyl 979 3-OMe,5-Cl N CF ₃ CF ₂ CHF ₂ 980 H N Et chfch ₃ 981 3-F N c-Propyl i-Propyl 982 3,5-Me ₂ N CP ₃ CF ₂ CHF ₂

112

99 • · · · · • · · • · · · · ♦ ♦ ♦ · • * · « • · · · • · 9 ·

9 9 9

No. From Y R ⁶ R ⁸ physical data 983 3-F,5-OMe 0 CH ₂ -c-Propyl cf ₃ 984 3-F 0 Me i-Propyl 985 H about c-Propyl CHFCH ₃ 986 3-F 0 H i-Propyl 987 H N H i-Propyl mp 143°C 988 3-Me,4-F About H i-Propyl 989 3-Me N c-Propyl chfch ₃ 990 3-OMe N Me cf ₃ 991 3-Cl,5-Me N n-Butyl cf ₂ chf ₂ 992 3-F N Me cf ₂ chf ₂ 993 3-Me,4-F N Me chfch ₃ 994 3-Me N c-Propyl CF(CH ₃ ) ₂ 995 3-CI N c-Propyl i-Propyl 996 3-F N c-Butyl cf ₂ chf ₂ 997 3-OMe N n-Butyl cf ₂ chf ₂ 998 3-Cl,5-Me N Benzyl i-Propyl 999 3-F,5-Me N H CF(CH ₃ ) ₂ 1000 H N Me cf ₂ chf ₂ 1001 3-CI N Et CF(CH ₃ ) ₂ 1002 H N c-Buty cf ₂ chf ₂ 1003 3.5-F N i-Propyl i-Propyl 1004 3-CF ₃ N c-Pentyl CP ₃ 1005 3-Me N Me i-Propyl t.t.1l2’C 1006 3-CI N Et chfch ₃ 1007 3-Me N c-Butyl i-Propyl 1008 3.5-Fj N n-Butyl CF ₂ CHF ₂

113

Table 10

Compounds of general formula Im (= formula I, where m = 0, n = 1, Y = -NHCONH-, R ³ ,R ⁴ ,R ⁵ ,R ⁷ ,R ⁹ ,R ¹⁰ = hydrogen atom and Aryl = substituted phenyl according to the table)

No. From R ⁶ R ⁸ physical data 1009 3-F Me CHFCH3 1010 H Et CF(CH ₃ ) ₂ 1011 3-Me c-Propyl i-Propyl 1012 3-CI Pentyl CF ₂ CHF ₂ 1013 3-F c-Butyl CHFCH ₃ 1014 3,5-Me ₂ t-Butyl i-Propyl 1015 3-CI.5-Me Me chfcf ₃ 1016 3-F,5-Me CH ₂ OEi CF(CH ₃ ) ₂ 1017 H Et cf ₂ chf ₂ 1018 3-F c-Propyl CF(CH ₃ ) ₂ 1019 3,5-Me _{2 CH2F} chfch ₃ 1020 3,5-Me ₂ s-Butyl chfch ₃ 1021 3-F,5-OMe CH ₂ -c-Eutyl i-Propyl 1022 H Me CF(CH ₃ ) ₂ 1023 3-Me _CH2OMe CF(CH ₃ ) ₂ 1024 3-Me Et cf ₂ chf ₂ 1025 3-CI Et cf ₂ chf ₂ 1026 H c-Butyl CF(CH ₃ ) ₂ 1027 3-Me c-Butyl CF(CH ₃ ) ₂ 1028 H Et Me 1029 3.5-F ₂ c-Pentyl CHFCH3 1030 3-CF ₃ i-Propyl i-Propyl 1031 H Et i-Propyl 1032 3-CI _CH2OEt CHFCH3

114

No. From R ⁶ R ⁸ physical data 1033 H _CH2OMe Me 1034 3-F,5-Me cf ₃ CHFCH ₃ 1035 3-Me Me CF(CH ₃ ) ₂ 1036 3-F c-Propyl cf ₂ chf ₂ 1037 3,5-(OMe) _{2 CH2} -c-Butyl cf ₃ 1038 3-F,5-OMe _CH2OEt chfch ₃ 1039 H H chfch ₃ 1040 3-Me Me cf ₂ chf ₂ 1041 3-CI Et i-Propyl 1042 3-F Et CF(CH ₃ ) ₂ 1043 H Et Et 1044 3-Me Pentyl CF ₂ CHF ₂ 1045 3.5-F ₂ Me cf ₃ 1046 3-OMe, 5-CI t-Butyl i-Propyl 1047 3-CF ₃ i-Butyl CF ₂ CHF ₂ 1048 3-CI Me cf ₂ chf ₂ 1049 H c-Propyl CF(CH ₃ ) ₂ 1050 3-CI c-Butyl cf ₂ chf ₂ 1051 3-OEt CHr c-Butyl i-Propyl 1052 H Me i-Propyl 1053 3-Me Me chfch ₃ 1054 3-F H CF(CH ₃ ) ₂ 1055 3-Me,4-F Me cf ₂ chf ₂ 1056 3-Me Et chfch ₃ 1057 3-F Et i-Propyl 1058 H c-Propyl cf ₂ chf ₂ 1059 3-CI c-Propyl CF(CH ₃ ) ₂ 1060 H s-Butyl Me 1061 3-Me c-Butyl CHFCH ₃ 1062 3-F c-Butyl CF(CH ₃ ) ₂ 1063 3-OMe c-Pentyl CHFCHs 1064 3,5-(OMe) _{2 CH2OMe} chfch ₃ 1065 3-OMe,5-CI H CF(CH ₃ ) ₂ 1066 3-OEt _CH2OEt CHFCH ₃ 1067 3-F,5-Me t-Butyl cf ₃

• · • ·

- 115 • «· 9 · · · > · · « · • * · · · · · · · • ·· · ·«·«·· • · · · · ··

No. From R ⁸ R ⁸ physical data 1068 3-CF3 Me CF(CH ₃ ) ₂ 1069 3-Me,4-F Me CF(CH ₃ ) ₂ 1070 3-Me c-Propyl cf ₂ chf ₂ 1071 3-OMe Pentyl i-Propyl 1072 3-Cl,5-Me c-Pentyl CHFCH ₃ 1073 3-Cl Me chfch ₃ 1074 3-Me Et i-Propyi 1075 H c-Propyl i-Propyl 1076 3-F c-Propyl chfch ₃ 1077 3-Cl c-Butyl chfch ₃ 1078 3,5-(OMe) ₂ CH ₂ -cPropyl CF(CH ₃ ) ₂ 1079 3-OEt i-Butyl cf ₃ 1080 3-F,5-OMe _CH2OMe cf ₂ chf ₂ 1081 3-Cl Me CF(CH ₃ ) ₂ 1082 3-F H cf ₂ chf ₂ 1083 3-Cl c-Butyl CF(CH ₃ ) ₂ 1084 3-OMe,5-CI _CH2F i-Propyl 1085 3-Cl Me i-Propyl 1086 3-F _CH2OEt CHFCH ₃ 1087 3-Cl c-Butyl i-Propyl 1088 3-OMe, 5-CI cf ₃ CF ₂ CHF ₂ 1089 H Et chfch ₃ 1090 3-F c-Propyl i-Propyl 1091 3,5-Me ₂ cf ₃ CF ₂ CHF ₂ 1092 3-F,5-OMe CHrC-Propyl cf ₃ 1093 3-F Me i-Propyl 1094 H c-Propyl chfch ₃ 1095 3-F H i-Propyl 1096 H H i-Propyl 1097 3-Me,4-F H i-Propyl 1098 3-Me c-Propyl chfch ₃ 1099 3-OMe Me cf ₃ 1100 3-Cl,5-Me n-Butyl cf ₂ chf ₂ 1101 3-F Me cf ₂ chf ₂ 1102 3-Me,4-F Me chfch ₃

• · • ·

- 116 ··· ··« ·· ··

No. From R ⁸ R ⁸ and physical data 1103 3-Me c-Propyl CF(CH ₃ ) ₂ 1104 3-CI c-Propyl i-Propyl 1105 3-F c-Butyl CF ₂ CHF ₂ 1106 3-OMe n-Butyl cf ₂ chf ₂ 1107 3-Cl,5-Me Hexyl i-Propyl 1108 3-F,5-Me H CF(CH ₃ ) ₂ 1109 H Me cf ₂ chf ₂ 1110 3-CI Et CF(CH ₃ ) ₂ 1111 H c-Butyl cf ₂ chf ₂ 1112 3.5-F ₂ i-Propyl i-Propyl 1113 3-CF ₃ c-Pentyl cf ₃ 1114 3-Me Me i-Propyl 1115 3-CI Et chfch ₃ 1116 3-Me c-Butyl i-Propyl 1117 3.5-F ₂ n-Butyl CF ₂ CHF ₂

Table 11

Compounds of general formula In (= formula I , where m = 1, Y = -NHCOO-, R ³ ,R ⁴ ,R ⁵ ,R ⁷ ,R ⁹ ,R ¹⁰ = hydrogen atom and = substituted phenyl according to the table), n = Aryl

(In)

R ⁸

No. From R ⁸ R ⁸ physical data 1118 3-Me,4-F H i-Propyl 1119 3-Me c-Propyl CHFCH ₃ 1120 3-OMe Me cf ₃ 1121 3-CI Pentyl cf ₂ chf ₂ 1122 3-F c-Butyl chfch ₃

• · ♦ ·

117

No. From R ⁶ R ⁸ physical data 1123 3,5-Me ₂ t-Butyl i-Propyl 1124 3-Cl,5-Me Me CHFCF ₃ 1125 3-F,5-Me _CH2OEt CF(CH ₃ ) ₂ 1126 H Et cf ₂ chf ₂ 1127 3-F c-Propyl CF(CH ₃ ) ₂ 1128 3-CI Et CF(CH ₃ ) ₂ 1129 H c-Buty cf ₂ chf ₂ 1130 3.5-F ₂ i-Propyi i-Propyl 1131 3-CF ₃ c-Pentyl CF ₃ 1132 3-Me Me i-Propyl 1133 3-F Me CHFCH ₃ 1134 H Et CF(CH ₃ ) ₂ 1135 3-Me c-Propyl i-Propyl 1136 3-Me Et CF ₂ CHF ₂ 1137 3-CI Et cf ₂ chf ₂ 1138 H c-Butyl CF(CH ₃ ) ₂ 1139 3-Me c-Butyl CF(CH ₃ ) ₂ 1140 H Et Me 1141 3.5-F ₂ c-Pentyl CHFCH ₃ 1142 3-CF3 i-Propyi i-Propyl 1143 H Et i-Propyi 1144 3-CI _CH2OEt CHFCH ₃ 1145 H _CH2OMe Me 1146 3-F,5-Me cf ₃ CHFCH ₃ 1147 3,5-Me ₂ ch ₂ f CHFCH ₃ 1148 3,5-Me ₂ s-Butyl chfch ₃ 1149 3-F,5-OMe _CH2 -c-Butyl i-Propyl 1150 H Me CF(CH ₃ ) ₂ 1151 3-Me _CH2OMe CF(CH ₃ ) ₂ 1152 3-Me Me CF(CH ₃ ) ₂ 1153 3-F c-Propyl cf ₂ chf ₂ 1154 3,5-(OMe) ₂ CHrC-Butyl cf ₃ 1155 3-F,5-OMe _CH2OEt chfch ₃ 1156 H H chfch ₃ 1157 3-Me Me cf ₂ chf ₂

118

No. From R ⁸ R ⁸ physical data 1158 3-CI Et i-Propyl 1159 3-F Et CF(CH ₃ ) ₂ 1160 H Et Et 1161 3-Me Pentyl CF ₂ CHF ₂ 1162 3.5-F ₂ Me cf ₃ 1163 3-OMe, 5-CI t-Butyl i-Propyl 1164 3-CF ₃ i-Butyl CF ₂ CHF ₂ 1165 3-CI Me cf ₂ chf ₂ 1166 H c-Propyl CF(CH ₃ ) ₂ 1167 3-CI c-Butyl cf ₂ chf ₂ 1168 3-OEt _CH2 -c-Butyl i-Propyl 1169 H Me i-Propyl 1170 3-Me Me CHFCH ₃ 1171 3-F H CF(CH ₃ ) ₂ 1172 3-Me,4-F Me cf ₂ chf ₂ 1173 3-Me Et chfch ₃ 1174 3-F Et i-Propyl 1175 H c-Propyl cf ₂ chf ₂ 1176 3-CI c-Propyl CF(CH ₃ ) ₂ 1177 H s-Eutyl Me 1178 3-Me c-Butyl CHFCH ₃ 1179 3-F c-Butyl CF(CH ₃ ) ₂ 1180 3-OMe c-Pentyl chfch ₃ 1181 3,5-(OMe) _{2 CH2OMe} CHFCH3 1182 3-OMe,5-CI H CF(CH ₃ ) ₂ 1183 3-OEt _CH2OEt chfch ₃ 1184 3-F,5-Me t-Butyl cf ₃ 1185 3-CF3 Me CF(CH ₃ ) ₂ 1186 3-Me,4-F Me CF(CH ₃ ) ₂ 1187 3-Me c-Propyl CF ₂ CHF ₂ 1188 3-OMe Pentyl i-Propyl 1189 3-Cl,5-Me c-Pentyl CHFCH ₃ 1190 3-CI Me CHFCH ₃ 1191 3-Me Et i-Propyl 1192 H c-Propyl i-Propyl

• · · · · · · ·

119

No. From R ⁶ R ⁸ physical data 1193 3-F c-Propyl chfch ₃ 1194 3-CI c-Butyl CHFCH ₃ 1195 3,5-(OMe) ₂ CH ₂ -cPropyl CF(CH ₃ ) ₂ 1196 3-OEt i-Butyl cf ₃ 1197 3-F,5-OMe _CH2OMe cf ₂ chf ₂ 1198 3-CI Me CF(CH ₃ ) ₂ 1199 3-F H cf ₂ chf ₂ 1200 3-CI c-Butyl CF(CH ₃ ) ₂ 1201 3-OMe,5-CI _CH2F i-Propyl 1202 3-CI Me i-Propyl 1203 3-F _CH2OEt chfch ₃ 1204 3-CI c-Butyl i-Propyl 1205 3-OMe,5-CI cf ₃ CF ₂ CHF ₂ 1206 H Et chfch ₃ 1207 3-F c-Propyl i-Propyl 1208 3,5-Me ₂ CF ₃ CF ₂ CHF ₂ 1209 3-F,5-OMe CH ₂ -c-Propyl cf ₃ 1210 3-F Me i-Propyl 1211 H c-Propyl chfch ₃ 1212 3-F H i-Propyl 1213 H H i-Propyl 1214 3-CI Et chfch ₃ 1215 3-Me c-Butyl i-Propyl 1216 3.5-F ₂ n-Butyl CF ₂ CHF ₂ 1217 3-Cl,5-Me n-Butyl cf ₂ chf ₂ 1218 3-F Me cf ₂ chf ₂ 1219 3-Me,4-F Me chfch ₃ 1220 3-Me c-Propyl CF(CH ₃ ) ₂ 1221 3-CI c-Propyl i-Propyl 1222 3-F c-Butyl CF ₂ CHF ₂ 1223 3-OMe n-Butyl cf ₂ chf ₂ 1224 3-Cl,5-Me Hexyl i-Propyl 1225 3-F,5-Me H CF(CH ₃ ) ₂ 1226 H Me cf ₂ chf ₂

- 120

Table 12

Compounds of general formula Io (=formula I, where m=1, n=1, Y= -ON=, R = binding site for double bond, R ⁴ ,R ⁵ ,R ⁷ ,R ⁹ ,R ¹⁰ = hydrogen atom and Aryl = substituted phenyl according to the table)

No. From R ⁶ R ⁸ physical data 1227 3-F,5-OMe _CH2OMe cf ₂ chf ₂ 1228 3-CI Me CF(CH ₃ ) ₂ 1229 3-F H cf ₂ chf ₂ 1230 3-CI Pentyl cf ₂ chf ₂ 1231 3-F c-Eutyl CHFCHa 1232 3,5-Me ₂ t-Butyl i-Propyl 1233 3-Cl,5-Me Me CHFCF ₃ 1234 3,5-Me ₂ H chfch ₃ resin 1235 3,5-Me ₂ H Et * resin 1236 3,5-Me ₂ H CF(CH ₃ ) ₂ resin 1237 H Et cf ₂ chf ₂ 1238 3-F c-Propyl CF(CH ₃ ) ₂ 1239 3-CI Et CF(CH ₃ ) ₂ 1240 H c-Butyl cf ₂ chf ₂ 1241 3.5-F ₂ i-Propyl i-Propyl 1242 3-CF ₃ c-Pentyl cf ₃ 1243 3-Me Me i-Propyl 1244 3-F Me chfch ₃ 1245 H Et CF(CH ₃ ) ₂ 1246 3-Me c-Propyl i-Propyl 1247 3-Me Et CF ₂ CHF ₂ 1248 3-CI Et cf ₂ chf ₂ 1249 H c-Butyl CF(CH ₃ ) ₂

121

I . From R ⁸ R ⁸ physical data 1250 3-Me c-Butyl CF(CH ₃ ) ₂ 1251 3,5-Me ₂ H CH(CH ₃ ) ₂ resin 1252 H H CF(CH ₃ ) ₂ resin 1253 H H CH(CH ₃ ) ₂ resin 1254 H Et Me 1255 3-Me,4-F H i-Propyi 1256 3-Me c-Propyl chfch ₃ 1257 3-OMe Me cf ₃ 1258 3.5-F ₂ c-Pentyl chfch ₃ 1259 3-CF ₃ i-Propyi i-Propyl 1260 H Et i-Propyl 1261 3-Cl _CH2OEt chfch ₃ 1262 H _CH2OMe Me 1263 3-F,5-Me CF ₃ chfch ₃ 1264 3,5-Me ₂ ch ₂ f chfch ₃ 1265 3,5-Me ₂ s-Butyl chfch ₃ 1266 3-F,5-OMe CHrC-Butyl i-Propyl 1267 H Me CF(CH ₃ ) ₂ 1268 3-Me _CH2OMe CF(CH ₃ ) ₂ 1269 3-Me Me CF(CH ₃ ) ₂ 1270 3-F c-Propyl cf ₂ chf ₂ 1271 3,5-(OMe) _{2 CH2} -c-Butyl cf ₃ 1272 3-F,5-OMe _CH2OEt chfch ₃ 1273 H H Me 1274 3-Me Me cf ₂ chf ₂ 1275 3-Cl Et i-Propyl 1276 3-F Et CF(CH ₃ ) ₂ 1277 H Et Et 1278 3-Me Pentyl CF ₂ CHF ₂ 1279 3.5-F ₂ Me cf ₃ 1280 3-OMe,5-CI t-Butyl i-Propyl 1281 3-CFa i-Shoes CF ₂ CHF ₂ 1282 3-Cl Me cf ₂ chf ₂ 1283 H c-Propyl CF(CH ₃ ) ₂ 1284 3-Cl c-Butyl cf ₂ chf ₂

122

No. From R ⁸ R ⁸ physical data 1285 3-OEt CHrC-Butyl i-Propyl 1286 H Me i-Propyl 1287 3-Me Me CHFCH ₃ 1288 3-F H CP(CH ₃ ) ₂ 1289 3-Me,4-F Me cf ₂ chf ₂ 1290 3-Me Et chfch ₃ 1291 3-F Et i-Propyl 1292 H c-Propyl CF ₂ CHF ₂ 1293 3-CI c-Propyl CF(CH ₃ ) ₂ 1294 H s-Butyl Me 1295 3-Me c-Butyl chfch ₃ 1296 3-F c-Butyl CF(CH ₃ ) ₂ 1297 3-OMe c-Pentyl chfch ₃ 1298 3,5-OMe _CH2OMe CHFCH ₃ 1299 3-OMe,5-CI H CF(CH ₃ ) ₂ 1300 3-OEt _CH2OEt chfch ₃ 1301 3-F,5-Me t-Butyl cf ₃ 1302 3-CP ₃ Me CF(CH ₃ ) ₂ 1303 3-Me,4-F Me CF(CH ₃ ) ₂ 1304 3-Me c-Propyl cf ₂ chf ₂ 1305 3-OMe Pentyl i-Propyl 1306 3-Cl,5-Me c-Pentyl CHFCH ₃ 1307 H H chfch ₃ resin 1308 3-CI Me chfch ₃ 1309 3-Me Et i-Propyl 1310 H c-Propyl i-Propyl 1311 3-F c-Propyl CHFCH ₃ 1312 3-CI c-Butyl CHFCH ₃ 1313 3,5-(OMe) ₂ CHrCPropyl CF(CH ₃ ) ₂ 1314 3-OEt i-Butyl cf ₃ 1315 3-Cl,5-Me Hexyl i-Propyl 1316 3-F,5-Me H CF(CH ₃ ) ₂ 1317 H Me cf ₂ chf ₂ 1318 3-CI c-Butyl CF(CH ₃ ) ₂ 1319 3-OMe,5-CI _CH2F i-Propyl

123

No. From R ⁸ R ⁸ physical data 1320 3-CI Me i-Propyl 1321 3-F _CH2OEt CHFCH ₃ 1322 3-CI c-Butyl i-Propyl 1323 3-OMe,5-CI cf ₃ CF ₂ CHF ₂ 1324 H Et chfch ₃ 1325 3-F c-Propyl i-Propyl 1326 3,5-Me ₂ cf ₃ CF ₂ CHF ₂ 1327 3-F,5-OMe CH _r c-Propyl cf ₃ 1328 3-F Me i-Propyl 1329 H c-Propyl CHFCH ₃ 1330 3-F H i-Propyl 1331 H H Et 1332 3-CI Et CHFCH ₃ 1333 3-Me c-Butyl i-Propyl 1334 3.5-F ₂ n-Butyl cf ₂ chf ₂ 1335 3-Cl,5-Me n-Buty cf ₂ chf ₂ 1336 3-F Me cf ₂ chf ₂ 1337 3-Me,4-F Me chfch ₃ 1338 3-Me c-Propyl CF(CH ₃ ) ₂ 1339 3-CI c-Propyl i-Propyi 1340 3-F c-Butyl CF ₂ CHF ₂ 1341 3-OMe n-Butyl cf ₂ chf ₂

• ·

124

Table 13

Compounds of general formula Ip (=formula I, where m=0, n=1, Y= -O-(CH ₂ )2 ^- θ>_; R ⁴ ,R5,R ² ,,rIO = hydrogen atom and Aryl = substituted phenyl according to the table)

No. From R ⁶ R ⁸ physical data 1342 3-F,5-Me cf ₃ chfch ₃ 1343 3,5-Me ₂ ch ₂ f CHFCH ₃ 1344 H Et CF(CH ₃ ) ₂ oil 1345 H Et CH(CH ₃ ) ₂ oil 1346 H Et CHFCH ₃ oil 1347 3-F H CF ₂ CHF ₂ 1348 3-Cl Pentyl cf ₂ chf ₂ 1349 3-F c-Butyl CHFCH ₃ 1350 3,5-Me ₂ t-Butyl i-Prcpyi 1351 3-Cl,5-Me Me chfcf ₃ 1352 3,5-Me ₂ H chfch ₃ 1353 3,5-Me ₂ H Et 1354 3,5-Me ₂ H CF(CH ₃ ) ₂ 1355 H Et cf ₂ chf ₂ 1356 3-F c-Propyl CF(CH ₃ ) ₂ 1357 3-Cl Et CF(CH ₃ ) ₂ 1358 H c-Butyl cf ₂ chf ₂ 1359 3.5-F ₂ i-Propyl i-Propyl 1360 3-CF ₃ c-Pentyl cf ₃ 1361 3-Me Me i-Propyl 1362 3-F Me chfch ₃ 1363 3-F,5-OMe _CH2OMe cf ₂ chf ₂ 1364 3-Cl Et CF(CH ₃ ) ₂ oil 1365 3-Me c-Propyl i-Propyl

125

No. From R ⁸ R ⁸ physical data 1366 3-Me Et cf ₂ chf ₂ 1367 3-Cl Et cf ₂ chf ₂ 1368 H c-Butyl CF(CH ₃ ) ₂ 1369 3-Me c-Butyl CF(CH ₃ ) ₂ 1370 3,5-Me ₂ H CH(CH ₃ ) ₂ 1371 H H CF(CH ₃ ) ₂ 1372 H H CH(CH ₃ ) ₂ 1373 H Et Me 1374 3-Me,4-F H i-Propyl 1375 3-Me c-Propyl CHFCH ₃ 1376 3-OMe Me cf ₃ 1377 3.5-F ₂ c-Pentyl chfch ₃ 1378 3-CFa i-Propyl i-Propyl 1379 3-Cl _CH2OEt chfch ₃ 1380 H _CH2OMe Me 1381 3-F c-Butyl CF ₂ CHF ₂ 1382 3-OMe n-Butyl cf ₂ chf ₂ 1383 3,5-Me ₂ s-Butyl chfch ₃ 1384 3-F,5-OMe _CH2 -c-Butyl i-Propyl 1385 H Me CF(CH ₃ ) ₂ oil 1386 3-Me _CH2OMe CF(CH ₃ ) ₂ 1387 3-Me Me CF(CH ₃ ) ₂ 1388 3-F c-Propyl cf ₂ chf ₂ 1389 3,5-(OMe) ₂ CHrC-Butyl cf ₃ 1390 3-F,5-OMe _CH2OEt CHFCH ₃ 1391 H H chfch ₃ 1392 3-Me Me cf ₂ chf ₂ 1393 3-Cl Et i-Propyl 1394 3-F Et CF(CH ₃ ) ₂ 1395 H Et Et 1396 3-Me Pentyl CF ₂ CHF ₂ 1397 3.5-F ₂ Me cf ₃ 1398 3-OMe,5-CI t-Butyl i-Propyl 1399 3-CF ₃ i-Butyl CF ₂ CHF ₂ 1400 3-Cl Me cf ₂ chf ₂

• ·

- 126

No. From R ⁶ R ⁸ physical data 1401 H c-Propyl CF(CH ₃ ) ₂ 1402 3-CI c-Butyl CF ₂ CHF ₂ 1403 3-OEt CHrC-Butyl i-Propyl 1404 H Me i-Propyl oil 1405 3-Me Me CHFCH ₃ 1406 3-F H CF(CH ₃ ) ₂ 1407 3-Me,4-F Me cf ₂ chf ₂ 1408 3-Me Et CHFCH ₃ 1409 3-F Et i-Propyl 1410 H c-Propyl cf ₂ chf ₂ 1411 3-CI c-Propyl CF(CH ₃ ) ₂ 1412 H s-Butyl Me 1413 3-Me c-Butyl chfch ₃ 1414 3-F c-Butyl CF(CH ₃ ) ₂ 1415 3-OMe c-Pentyl CHFCH ₃ 1416 3,5-(OMe) _{2 CH2OMe} chfch ₃ 1417 3-CMe,5-CI H CF(CH ₃ ) ₂ 1418 3-OEt _CH2OEt chfch ₃ 1419 3-F,5-Me t-Butyl cf ₃ 1420 3-CF ₃ Me CF(CH ₃ ) ₂ 1421 3-Me,4-F Me CF(CH ₃ ) ₂ 1422 3-Me c-Propyl cf ₂ chf ₂ 1423 3-OMe Pentyl i-Propyl 1424 3-Cl,5-Me c-Pentyl chfch ₃ 1425 H H CHFCH ₃ 1426 3-CI Me chfch ₃ 1427 3-Me Et i-Propyl 1428 H c-Propyl i-Propyl 1429 3-F c-Propyl chfch ₃ 1430 3-CI c-Butyl CHFCH3 1431 3,5-(OMe) ₂ CHrcPropyl CF(CH ₃ ) ₂ 1432 3-OEi i-Shoes cf ₃ 1433 3-Cl,5-Me Hexyl i-Propyl 1434 3-F,5-Me H CF(CH ₃ ) ₂ 1435 H Me cf ₂ chf ₂

• ·

- 127

No. From R ⁸ R ⁸ physical data 1436 3-CI c-Butyl CF(CH ₃ ) ₂ 1437 3-OMe,5-CI _CH2F i-Propyl 1438 3-CI Me i-Propyl 1439 3-F _CH2OEt chfch ₃ 1440 3-CI c-Butyl i-Propyi 1441 3-OMe,5-CI cf ₃ cf ₂ chf ₂ 1442 3-F c-Fropyi i-Propyi 1443 3,5-Me ₂ cf ₃ cf ₂ chf ₂ 1444 3-F,5-OMe CH ₂ -c-Propyl cf ₃ 1445 3-F Me i-Propyi 1446 H c-Propyl chfch ₃ 1447 3-F H i-Propyi 1448 H H i-Propyl 1449 3-CI Et chfch ₃ 1450 3-Me c-Buty i-Propyl 1451 3.5-F ₂ n-Butyl CF ₂ CHF ₂ 1452 3-Cl,5-Me n-Butyl cf ₂ chf ₂ 1453 3-F Me cf ₂ chf ₂ 1454 3-Me,4-F Me chfch ₃ 1455 3-Me c-Propyl CF(CH ₃ ) ₂ 1456 3-CI c-Propyl i-Propyl

128

B) Examples of formulations

Example B1

Spray preparation

The spray preparation is obtained by mixing 10 parts by weight of the compound of general formula I and 90 parts by weight of talc as an inert substance and grinding them in a hammer mill.

Example B2

Dispersible powder

A water-dispersible, wettable powder is obtained by mixing 25 parts by weight of a compound of general formula I, 64 parts by weight of kaolin containing silica as an inert substance, 10 parts by weight of potassium lignin sulfonate and 1 part by weight of sodium oleylmethyl taurate as a wetting and dispersing agent, and grinding this mixture in a pin mill.

Example B3

Dispersion concentrate

A water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of a compound of the general formula I with 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 of about 255 °C to over

129 • ·

277 °C) and this mixture is ground in a ball mill to a fineness below 5 microns.

Example B4

Emulsifiable concentrate

An emulsifiable concentrate is obtained from 15 parts by weight of a compound of general formula I, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.

Example B5

Water-dispersible granules

The water-dispersible granulate is obtained by mixing 10 parts by weight, 5 parts by weight, 3 parts by weight, 7 parts by weight of the compound of general formula I, calcium lignin sulfonate, sodium lauryl sulfate, polyvinyl alcohol and kaolin, this mixture is ground in a cake mill and the obtained powder is granulated in a fluidized bed while spraying water as a granulating liquid.

Example B6

Water-dispersible granules

Water-dispersible granules are also obtained by

- 130 • c

that 5 parts by weight 1 part by weight 17 parts by weight 50 parts by weight of the compound of general formula I, sodium salt of 2,2'-dinaphthylmethane-6,6'-disulfonic acid, sodium oleylmethyltaurate, polyvinyl alcohol, calcium carbonate and water are homogenized in a colloid mill and pre-ground, then ground in a pearl mill and the suspension thus obtained is sprayed in a spray tower using a single-component nozzle and dried.

C) Biological examples

Example Cl

Pre-emergence weed control

Seeds of monocotyledonous and dicotyledonous weed plants are sown in plastic pots in loamy sandy soil and covered with soil. The compounds according to the present invention, formulated as wettable powders or emulsion concentrates, are then applied as aqueous suspensions or emulsions, with a water amount of approximately 600 to 800 l/ha, in various doses to the surface of the covering soil. After treatment, the pots are placed in a greenhouse and maintained there under good growth conditions for weeds. The optical quality of the plants, or their damage after emergence, is carried out after the emergence of these test plants after a trial period of 3 to 4 weeks in comparison with the untreated control. As the test results show, the compounds according to the present invention have good ♦ <* »» · · »» *9 • «« · 9« · O · · ♦ ·

9 9 » · * *

-í 7-1 · 99· · · · * “ ± J? ± “ « « · « · t <f · pre-emergence herbicidal efficacy against a wide range of weedy grasses and weeds. For example, compounds according to

examples 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, 134 5, 1346, 1364, 1385

and 1404 good and mostly very good herbicidal efficacy against harmful plants such as Stellaria media, Amaranthus retroflexus, Sinapsis avreuse, Avena fatura, Lolium multiflorum and Setaria Viridis when applied pre-emergence and at a rate of 3.0 kg or less of active substance per hectare.

Example C2

Post-emergence weed control

Seeds of monocotyledonous and dicotyledonous weed plants are sown in plastic pots in loamy sandy soil, covered with soil and placed in a greenhouse under good growth conditions. Two to three weeks after sowing, the test plants are treated at the three-leaf stage. The compounds according to the present invention, formulated as spray powders or as emulsion concentrates, are sprayed onto the green parts of the plants at various dosages using an applied amount of water of approximately 600 to 800 l/ha and after about 3 to 4 weeks of standing of the test plants in the greenhouse under optimal growth conditions, the effect of the preparations is evaluated optically in comparison with the untreated control. The compositions according to the present invention also have good herbicidal » · * ·

132 have efficacy against a wide range of agriculturally important weedy grasses and weeds. For example, compounds according to the example

ladies 20, 23, 41, 42, 43, , 46 , 78, 80, 18 3, 1 84, 201, 20 '7, 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 , 123' 1, 12 35, 12 ,36 , 1251, 1252,

1253, 1307, 1344, 1345, 1346, 1364, 1385 and 1404 good to very good herbicidal efficacy against harmful plants such as Stellaria media, Amaranthus retroflexus, Sinapsis avreuse, Avena fatura, Lolium multiflorum and Setaria viridis in the pre-emergence procedure and at an application rate of 3.0 kg or less of active substance per hectare.

Example C3

Effects on harmful plants in rice

Typical harmful plants in rice crops Echinocloa crus gali and Cyperus iria are grown in a greenhouse under suitable conditions (maintained water height: 2 to 3 cm). The test plants are then treated with the compounds according to the present invention. After the treatment, the test plants are placed in a greenhouse under optimal growth conditions and are left there for the entire test period. The optical quality of the plants, or their damage, is evaluated after about 3 weeks in comparison with the untreated control. As the test results show, the compounds according to the present invention have very good herbicidal activity against harmful plants. For example, the compounds according to Examples 41, 42, 46, 120, 183, 201, 207, 213, 220, 222, 228, 231,

245, 253, 281, 299, 300, 303, 308, 311, 326, 336, 340, 347,

133

358, 368, 369, 370, 372, 376, 380, 381, 384 and 394 have very good herbicidal efficacy against Cyperus iria and Echinochloa crus-galli.

Example C4

Tolerance by cultivated plants

In further experiments, seeds of a large number of crop plants and weeds are sown in a sandy loam soil in a greenhouse and covered with a cover soil. One part of the pots is treated immediately, as described in Example Cl., while the other part is placed in a greenhouse and waited until the plants have developed two to three true leaves, and then, as described in Example C2, sprayed with the compounds of the present invention in various doses. Four to five weeks after application and standing in the greenhouse, it is found by optical observation that the compounds of the present invention do not harm crop plants in the two-leaf stage, such as soybeans and sugar beets, in both pre-emergence and post-emergence treatments, even at high concentrations of active ingredients. In addition, some of the substances are particularly gentle on crops such as barley, wheat and rice.

The compounds of the general formula I therefore have a partly high selectivity and are therefore suitable for controlling unwanted plant growth in agricultural crops.

Claims (10)

PATENT CLAIMS 1. Substituted 2,4-diamino-1,3,5-triazines of the general formula I, optionally in the form of their salts in which Aryl denotes an optionally substituted monocyclic or bicyclic aromatic radical with 5 to 14 ring atoms, of which 1, 2, 3 or 4 may independently be from the group consisting of oxygen, sulfur and nitrogen, -Y- denotes a divalent unit from the group consisting of -0-, -S-, -NR ¹¹ -, -NR ¹² C0NR ¹³ -, -C02-, -OC02-, -OC0NR ¹⁴ -, -SO-, -S02-, -S0 ₂ 0-, -OS0 ₂ 0- and -SO ₂ NR ¹⁴ -, or also from the group consisting of -0-NR ¹¹ -, -NR'-NR'', wherein R' and R'' are independently defined as R ¹⁴ , and - (Y'-CR ^a R ^b -CR ^c R ^d ) j·-Y'' , wherein Y' and Y'' independently represent an oxygen atom, a sulfur atom or an N-alkyl group with 1 to 4 carbon atoms, R ^a , R ^b , R ^c and R ^d independently represent a hydrogen atom • · - 135 or an alkyl group with 1 to 4 carbon atoms and i represents an integer from 1 to 5, preferably 1, but also a trivalent unit of the formula -O-N=, m represents the number 0, 1, 2, 3, 4 or 5, n represents an integer from 1 to 10, with the proviso that n does not represent 1 when m represents zero and Y represents the group -O-, -S-, -SO-, -SO2- or -NrH-, Ί 9 R ^x and R each independently denote a residue of the group G1, comprising a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, an alkenyl group with 2 to 8 carbon atoms, an alkynyl group with 2 to 8 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkoxy group with 3 to 8 carbon atoms, an arylalkyl group with 1 to 6 carbon atoms in the alkyl and a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the alkyl, wherein the cyclic parts of the four latter-mentioned radicals are optionally substituted by one or more, the same or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a group -BX^ , wherein -B- and X^ are defined below and wherein the non-cyclic parts of the eight latter-mentioned radicals of the group G1 are optionally substituted by one or more, the same or different radicals from groups including halogen atom, nitro group, cyano group, thiocyanato group and group136 * ·· · · · · · · · · · · · • · · · ···· • » · · ·♦···· 2 2 · zz pinu -BX ^Z , wherein -B and X are defined below and wherein the non-cyclic parts of the residues of the group G1 may be interrupted by one or more, identical or different, heteroatoms from the group comprising an oxygen atom and a sulfur atom, or 12 12 R ^x and R ^of the group (CR R ) form with the carbon atom carrying it a carbonyl group, a CR ¹³ r16 group _{or a} three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group comprising an oxygen, nitrogen and sulphur atom and is optionally substituted by one or more, the same or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a -BX ¹ group, or 1 12 two R of two directly or indirectly adjacent groups (CR R ) form with the carbon atoms carrying them or connecting them an optionally substituted three- to six-membered ring, which optionally contains one or two identical or different heteroatoms from the group comprising an oxygen, nitrogen and sulphur atom and which is optionally substituted by one or more identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a -BX ¹ group, or 1 12 two R of two directly adjacent groups (CR R ) together with the bond between the carbon atoms of the groups denotes a double 1 2 bond or two R and two R of two directly adjacent groups (CR R ) together with the bond between the carbon atoms of the groups denotes a triple bond, or also 137 • · r! denotes the binding site for the double bond in the case where 1 2 Y denotes the trivalent unit =N-0- adjacent to the CR R group, R ³ , R ⁴ each independently of one another denote a residue of the group G2, comprising a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, an alkenyl group with 2 to 8 carbon atoms, an alkynyl group with 2 to 8 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, an alkylthio group with 1 to 10 carbon atoms, an alkylsulfinyl group with 1 to 10 carbon atoms, an alkylsulfonyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkoxy group with 3 to 8 carbon atoms, an aryl group, an arylalkyl group with 1 to 6 carbon atoms in the alkyl, an arylalkoxy group with 1 to 6 carbon atoms in the alkoxy, a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the alkyl, a cycloalkylalkoxy group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the carbon atoms in the alkoxy, a cycloalkoxyalkyl group with 3 to 8 carbon atoms in the cycloalkoxy and with 1 to 6 carbon atoms in the alkyl and a cycloalkoxyalkoxyl group with 3 to 8 carbon atoms in the cycloalkoxy and with 1 to 6 carbon atoms in the alkoxy, wherein the cyclic part of the nine latter-mentioned radicals is optionally substituted by one or more, the same or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a group -BX ² , wherein -B- and X ⁴ are defined below and wherein the non-cyclic part of the sixteen latter-mentioned radicals of the group G2 is optionally substituted by one or more, the same • · - 138 or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a group -B-X, wherein X is defined below and wherein the non-cyclic part of the radicals of the group G2 may be interrupted by one or more, identical or different, heteroatoms from the group comprising oxygen and sulfur, or R ³ and R ⁴ form a carbonyl group with the carbon atom carrying them. -1 < -I zt group, CR ^J R ° group or a three- to six-membered ring, which optionally contains one or two, identical or different heteroatoms from the group comprising an oxygen, nitrogen and sulfur atom and is optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a -BX group, or two R ^J of two directly or indirectly adjacent groups (CR R ) form with the carbon atoms carrying them, or optionally connecting them, an optionally substituted three- to six-membered ring, which optionally contains one or two identical or different heteroatoms from the group comprising an oxygen, nitrogen and sulfur atom and which is optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a -BX ⁴ group, or also two R ^J of two directly adjacent groups (CR ^J Rj together with the bond between the carbon atoms of the groups denotes a double bond or two R ³ and two R ⁴ of two directly adjacent groups (CR ³ R ⁴ ) together with the bond between the carbon atoms of the groups denotes a triple bond, or also • · 139 R ³ indicates the binding site for the double bond in the case where -i 9 Y denotes the trivalent unit -0-N= adjacent to the CR R group, -B- denotes a direct bond or a divalent unit from the group consisting of -0-, -S-, -NR^ ² -, -NR^ ² C0NR ²³ -, -C02-, -OC02-, -OC0NR ¹⁴ -, -S0-, -S02-, -S0 ₂ 0-, -OS0 ₂ 0- and -so ₂ nr ¹⁴ -, χΐ denotes a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, an alkenyl group with 2 to 8 carbon atoms, an alkynyl group with 2 to 8 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms or a heterocyclyl group with 3 to 9 ring atoms, of which 1, 2 or 3 come from the group consisting of a nitrogen, oxygen and sulfur atom and wherein the five latter radicals are optionally substituted by one or more, the same or different atoms halogen, and X represents a hydrogen atom or a heterocyclyl group with 3 to 9 ring atoms, of which 1, 2 or 3 are from the group consisting of nitrogen, oxygen and sulfur, optionally substituted by one or more, identical or different, halogen atoms, R ³ , r 6 independently of each other denote the residue of the group G 2 , or ac R and R of two directly or indirectly adjacent groups (CR ³ R ⁴ )- or (CR ³ R^)- form together with the carbon atom connecting them an optionally substituted three- to six-membered ring, which optionally • · • · • · · * - 140 - .·' .·* contains one or two, identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is optionally substituted by one or more, identical or different radicals from the group consisting of halogen atom, nitro group, cyano group, thiocyanato group and -BX ¹ group, or R ⁵ and R ⁶ form with the carbon atom carrying them a carbonyl group, a group CR ¹³ R ¹ ^ or a three- to six-membered ring, which optionally contains one or two identical or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a -BX ¹ group, or r 6 denotes a heterocyclyl radical, R denotes a hydrogen atom, an amino group, an alkylcarbonyl, alkylamino or dialkylamino group with 1 to 6 carbon atoms in the alkyl radicals, an acyclic hydrocarbon radical or hydrocarbonoxy radical with 1 to 6 carbon atoms in each case, a cyclic hydrocarbon radical or hydrocarbonoxy radical with 3 to 6 carbon atoms in each case or a heterocyclyl, heterocyclyloxy or heterocyclylamino radical with 3 to 6 ring atoms in each case and with one to three ring heteroatoms from the group comprising nitrogen, oxygen and sulphur, each of the ten latter radicals being optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, an alkoxy group with 1 to 4 carbon atoms, a haloalkoxy group with 1 to 4 carbon atoms, an alkylthio group with 1 • · 141 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, an alkenyloxy group with 2 to 4 carbon atoms, an alkynyloxy group with 2 to 4 carbon atoms, a hydroxy group, an amino group, an acylamino group, an alkylamino group, a dialkylamino group, a nitro group, a carboxy group, a cyano group, an azido group, an alkoxycarbonyl group with 1 to 4 carbon atoms in the alkoxy, an alkylcarbonyl group with 1 to 4 carbon atoms in the alkyl, a formyl group, a carbamoyl group, an alkylaminocarbonyl and a dialkylaminocarbonyl group with 1 to 4 carbon atoms in each case in the alkyl, an alkylsulfinyl group with 1 to 4 carbon atoms, a haloalkylsulfinyl group with 1 to 4 carbon atoms, an alkylsulfonyl group with 1 up to 4 carbon atoms, a haloalkylsulfonyl group with 1 to 4 carbon atoms and, in the case of cyclic radicals, also an alkyl group with 1 to 4 carbon atoms and a haloalkyl group with 1 to 4 carbon atoms, O R° denotes an alkyl group with 1 to 10 carbon atoms, an alkenyl group with 2 to 8 carbon atoms, an alkynyl group with 2 to 8 carbon atoms, which are optionally substituted by one or more, identical or different radicals from the group consisting of a halogen atom, a cyano group, a nitro group, a thiocyanato group, a hydroxy group, an alkoxy group with 1 to 4 carbon atoms, an alkylthio group with 1 to 4 carbon atoms, an alkylsulfinyl group with 1 to 4 carbon atoms, an alkylsulfonyl group with 1 to 4 carbon atoms, a phenyl group, a cycloalkyl group with 3 to 9 carbon atoms, a cycloalkoxy group with 3 to 9 carbon atoms and optionally one or more, identical 142 or by different radicals from the group consisting of a halogen atom, an amino group, an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, a haloalkyl group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, a substituted heterocyclyl group with three to six ring atoms and with one to three heteroatoms from the group consisting of oxygen, nitrogen and sulfur, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkoxy group with 3 to 8 carbon atoms or a heterocyclyl group with 3 to 6 ring atoms, the latter three radicals being optionally substituted by one or more, identical or different radicals from the group consisting of a halogen atom, a nitro group, a cyano group, a thiocyanato group, an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms atoms, a haloalkyl group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, R ⁹ , R ¹ ® independently of one another denote a hydrogen atom, an amino group, an alkylcarbonyl group with 1 to 10 carbon atoms in the alkyl, an alkylamino group with 1 to 10 carbon atoms, a dialkylamino group with 1 to 10 carbon atoms in each alkyl, an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, a cycloalkoxy group with 3 to 8 carbon atoms, a heterocyclyl, heterocyclyloxy or heterocyclylamino group with 3 to 6 ring atoms in each case and with 1 to 3 heteroatoms from the group comprising oxygen, nitrogen and sulfur, each of the ten last-mentioned radicals being optionally substituted, or _and r 10 together with the nitrogen atom carrying it form a heterocycle with a total of three to six ring atoms, of which one to four ring heteroatoms, wherein in addition to the nitrogen atom present, there are optionally further ring heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, and this heterocycle is optionally substituted, R ¹¹ represents a hydrogen atom, an amino group, an alkylamino group with 1 to 10 carbon atoms, a dialkylamino group with 1 to 10 carbon atoms in each alkyl, an alkyl group with 1 to 10 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and 1 to 6 carbon atoms in the alkyl, an alkoxy group with 1 to 10 carbon atoms, an alkoxyalkoxy group with 1 to 6 carbon atoms in each alkoxy, a cycloalkoxy group with 3 to 8 carbon atoms, an alkylcarbonyl group with 1 to 10 carbon atoms in the alkyl, the nine latter radicals being optionally substituted, 19 1 9 R , R ^±-? independently represent a hydrogen atom, an alkyl group with 1 to 10 carbon atoms, an alkenyl group with 2 to 8 carbon atoms, an alkynyl group with 2 to 8 carbon atoms, a phenyl group, a phenylalkyl group with 1 to 6 carbon atoms in the alkyl, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the alkyl, wherein the cyclic part of the last four names• · - 144 valent radicals are optionally substituted by one or more, identical or different radicals from the group consisting of alkyl group with 1 to 4 carbon atoms, haloalkyl group with 1 to 4 carbon atoms, alkoxy group with 1 to 4 carbon atoms and haloalkoxy group with 1 to 4 carbon atoms, or 12 12 R and R ^J together with the N-CO-N group carrying them form a five- to eight-membered ring, which in addition to the two nitrogen atoms mentioned may contain another heteroatom from the group comprising oxygen, nitrogen and sulfur and which is optionally substituted, R ⁴⁴ represents a hydrogen atom or an optionally substituted alkyl group or cycloalkyl group with 3 to 10 carbon atoms, R ⁴³ , R ¹ ^ independently represent a hydrogen atom, an aryl group, an alkoxy group with 1 to 10 carbon atoms, an arylalkyl group with 1 to 6 carbon atoms in the alkyl, an alkyl group with 1 to 10 carbon atoms, an alkylthio group with 1 to 10 carbon atoms, wherein five of the latter radicals are optionally substituted and wherein the aliphatic carbon structure of the three latter radicals may be interrupted by one or more, identical or different, heteroatoms from the group comprising oxygen and sulfur, or 1 c Ί A R " and R ^XD form with the carbon atom bearing them a three- to six-membered ring, which optionally contains one or two, the same or different, heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is 145 optionally substituted . 2. Substituted 2,4-diamino-1,3,5-triazines of general formula I according to claim 1, in which Aryl denotes an optionally substituted monocyclic or bicyclic aromatic radical with 5 to 10 ring atoms, of which 1, 2, 3 or 4 may independently be from the group consisting of oxygen, sulfur and nitrogen, -Y- denotes a divalent unit from the group including -O-, -S-, -NR ¹¹ -, -NR ¹² C0NR ¹³ -, -C02-, -OC0NR ¹⁴ -, -S0-, -S02-, -S0 ₂ 0- and -S0 ₂ NR ¹⁴ -, or also a divalent unit from the group comprising -0-NR ¹¹ -, -NH-NH and -0-CR ^and R ^b -CR ^c R ^d -0- , wherein R ^a , R ^b , R ^c and R ^d independently represent a hydrogen atom, a methyl or ethyl group, or also a trivalent unit of the formula -O-N= , and 1 9 R and R each independently represent a residue of the group G3, comprising a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkoxy group with 3 to 8 carbon atoms, an arylalkyl group with 1 to 6 carbon atoms in the alkyl and a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms 146 • · 4 « » · ·· · < e »« t · · » · * <* · * < » · · r ··· t » * # · · «»·* ··· »«t* ··· *«» ·* ·· in alkyl, wherein the cyclic parts of the four latter-named radicals are optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX ⁴ group, wherein -B- and X ⁴ are defined below and wherein the non-cyclic parts of the eight latter-named radicals of the G3 group are optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX 4 group, wherein -B and X are defined below and wherein the non-cyclic parts of the radicals of the G3 group may be interrupted by one or more, identical or different heteroatoms from the group comprising an oxygen atom and a sulfur atom, or i 2 12 R and R^ groups (CR R ) form with the carbon atom carrying it a carbonyl group, a CR ⁴ ^R ⁴ ^ group or a three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by one or more, the same or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX ⁴ group, or two R ⁴ of two directly or indirectly adjacent groups i 2 (CR R ) form with the carbon atoms carrying them, optionally connecting them an optionally substituted three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by one or more, the same or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX^ group, or 1 1 9 vx two R ¹ of two directly adjacent groups (CR R ) together with the bond between the carbon atoms of the groups indicates a double -j 9 bond or two R and two R of two directly adjacent 1 9 groups (CR R ) together with the bond between the carbon atoms of the groups denotes a triple bond, or r! denotes the binding site for a double bond in the case that 1 9 Y denotes the trivalent unit =N-0- adjacent to the CR R group, and R ³ , R ⁴ each independently of one another denote a residue of the group G4, comprising a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkoxy group with 3 to 8 carbon atoms, an aryl group, an arylalkyl group with 1 to 6 carbon atoms in the alkyl, an arylalkoxy group with 1 to 6 carbon atoms in the alkoxy, a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the alkyl, a cycloalkylalkoxy group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the alkoxy, a cycloalkoxyalkyl group with 3 to 8 carbon atoms in the cycloalkoxy and with 1 to 6 carbon atoms in the alkyl and a cycloalkoxyalkoxy group with 3 to 8 carbon atoms in the cycloalkoxy and with 1 to 6 carbon atoms in the alkoxy, wherein the cyclic part of the nine latter-named radicals is optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a -BX ¹ group, wherein -B- and X ¹ are defined below and wherein the non-cyclic part of the thirteen latter-named radicals of the G4 group is optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a -BX 1 group, wherein X is defined below and wherein the non-cyclic part of the radicals of the G4 group may be interrupted by one or two, identical or different heteroatoms from the group comprising oxygen and sulfur, or R ^{2 3} and R ⁴ form with the carbon atom bearing them a carbonyl group, a group CR ¹³ R ^1b or a three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by one or more, the same or different radicals from the group comprising a hydrogen atom, a nitro group, a cyano group and a -BX ¹ group, or 2 2 4 two R ^J of two directly or indirectly adjacent groups (CR ^J R ) form with the carbon atoms carrying them, optionally connecting them, an optionally substituted three- to six-membered ring, which optionally contains one or two, identical or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX ¹ group, or two R ³ of two directly adjacent groups (CR ³ R ⁴ ) denote a co• · • · - 149 with the bond between the carbon atoms of the groups a double bond or two R ³ and two R ⁴ of two directly adjacent groups (CR ³ R ⁴ ) together with the bond between the carbon atoms of the groups means a triple bond, or R denotes the binding site for the double bond in the case where Y denotes the trivalent unit -0-N= adjacent to the CR ³ R ⁴ group, and -B- denotes a direct bond or a divalent unit from the group consisting of -0-, -S-, -NR ⁴⁴ -, -CO-, -CC^-, -OCC^-, -S0-, -S0 ₂ -, -S0 ₂ 0- and -SO ₂ NR ¹⁴ - , X ⁴ represents a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms or a heterocyclyl group with 3 to 6 ring atoms, of which 1, 2 or 3 are derived from the group consisting of a nitrogen, oxygen and sulfur atom and wherein the five latter radicals are optionally substituted by one or more, identical or different, halogen atoms, X represents a hydrogen atom or a heterocyclyl group with 3 to 9 ring atoms, of which 1, 2 or 3 are from the group consisting of nitrogen, oxygen and sulfur, optionally substituted by 1, 2 or 3 identical or different halogen atoms, R ³ , r 6 independently represent the residue of the group G 4 , or R ³ and R ⁵ of two directly or indirectly adjacent groups 150 (CR ³ R ⁴ ) or (CR ³ R^) together with the carbon atoms connecting them form an optionally substituted three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is optionally substituted by one or more, the same or different radicals from the group consisting of a halogen atom, a nitro group, a cyano group and a -BX^ group, or R ⁵ and R ⁶ form with the carbon atom bearing them a carbonyl group, a CR^R^ group or a three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by one or more, the same or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX^ group, or R° represents a heterocyclyl group, R denotes a hydrogen atom, an amino group, an alkylcarbonyl, alkylamino or dialkylamino group with 1 to 4 carbon atoms in the alkyl radicals, an acyclic or cyclic hydrocarbon radical with 1 to 6 carbon atoms in each case or a heterocyclyl radical with 3 to 6 ring atoms and with one to three heteroatoms in the ring from the group comprising nitrogen, oxygen and sulphur, each of the six latter radicals being optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, an alkoxy group with 1 to 4 carbon atoms, a haloalkoxy group with 1 to 4 carbon atoms, an alkylthio group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, alkenyloxy group with 2 to 4 carbon atoms, alkynyloxy group with 2 to 4 carbon atoms, hydroxy group, amino group, alkylamino group, dialkylamino group, nitro group, carboxy group, cyano group, alkoxycarbonyl group with 1 to 4 carbon atoms in alkoxy, alkylcarbonyl group with 1 to 4 carbon atoms in alkyl, formyl group, carbamoyl group, alkylaminocarbonyl and dialkylaminocarbonyl groups with 1 to 4 carbon atoms in alkyl, alkylsulfonyl group with 1 to 4 carbon atoms, haloalkylsulfonyl group with 1 to 4 carbon atoms and in the case of cyclic radicals also alkyl group with 1 to 4 carbon atoms and haloalkyl group with 1 to 4 carbon atoms, O R denotes an alkyl group with 1 to 6 carbon atoms, which is optionally substituted by one or more, identical or different, radicals from the group comprising a halogen atom, a cyano group, a nitro group, a thiocyanato group, a hydroxy group, an alkoxy group with 1 to 4 carbon atoms, an alkylthio group with 1 to 4 carbon atoms, an alkylsulfonyl group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, a phenyl group, a cycloalkyl group with 3 to 9 carbon atoms, a cycloalkoxy group with 3 to 9 carbon atoms and optionally one or more, identical or different, radicals from the group comprising a halogen atom, an amino group, an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms I « · · 152 atoms, a haloalkyl group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, a substituted heterocyclyl group with three to six ring atoms and with one to three heteroatoms in the ring from the group comprising oxygen, nitrogen and sulphur, a cycloalkyl group with 3 to 8 carbon atoms or a cycloalkoxy group with 3 to 8 carbon atoms, the latter two radicals being optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, a haloalkyl group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, , R1® independently denotes a hydrogen atom, an amino group, an alkylcarbonyl group with 1 to 6 carbon atoms in alkyl, alkylamino group with 1 to 6 carbon atoms, dialkylamino group with 1 to 6 carbon atoms in each alkyl, alkyl group with 1 to 6 carbon atoms, cycloalkyl group with 3 to 8 carbon atoms, alkoxy group with 1 to 6 carbon atoms, cycloalkoxy group with 3 to 6 carbon atoms or heterocyclyl group with 3 to 6 ring atoms and with 1 to 3 ring heteroatoms from the group comprising oxygen, nitrogen and sulphur, each of the eight latter radicals being optionally substituted by one or more, identical or different radicals from the group comprising halogen atom, amino group, hydroxy group and in the case of cyclic radicals also alkyl group with 1 to 4 carbon atoms, alkoxy group with 1 to 4 carbon atoms, haloalkyl• · 153 a halo group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, or R ⁹ and R ⁷ ® together with the nitrogen atom carrying them form a heterocycle with a total of three to six ring atoms and one to four ring heteroatoms, where in addition to the nitrogen atom present there are optionally further ring heteroatoms selected from the group comprising oxygen, nitrogen and sulphur and this heterocycle is optionally substituted by one to three, identical or different radicals from the group comprising a halogen atom, an amino group, a hydroxy group, an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, a haloalkyl group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, rH denotes a hydrogen atom, an amino group, an alkylamino group with 1 to 6 carbon atoms, a dialkylamino group with 1 to 6 carbon atoms in each alkyl, an alkyl group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the alkyl, an alkoxy group with 1 to 6 carbon atoms, an alkoxyalkoxy group with 1 to 6 carbon atoms in each alkoxy, a cycloalkoxy group with 3 to 8 carbon atoms and an alkylcarbonyl group with 1 to 6 carbon atoms in the alkyl, the nine latter radicals being optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, an amino group, a hydroxy group and in the case of cyclic radicals also an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, a haloalkyl group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, 12 12 R ^x , R ^J independently represent a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a phenyl group, a phenylalkyl group with 1 to 6 carbon atoms in the alkyl, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the alkyl, the cyclic part of the four latter radicals being optionally substituted by one or more, identical or different radicals from the group comprising an alkyl group with 1 to 4 carbon atoms, a haloalkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, or 12 12 R and R together with the N-CO-N group carrying them form a five- to eight-membered ring, which in addition to the two nitrogen atoms mentioned may contain another heteroatom from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by one or more, identical or different, radicals from the group comprising a halogen atom, an alkyl group with 1 to 4 carbon atoms and a haloalkyl group with 1 to 4 carbon atoms, R ⁴⁴ represents a hydrogen atom or optionally one or more, identical or different, radicals from the group consisting of a halogen atom, a phenyl group, a hydroxy group, an alkoxy group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, an alkyl group with 1 to 6 carbon atoms or a cycloalkyl group with 3 to 8 carbon atoms, and -i c Ί A R , _R ±O independently represent a hydrogen atom, a phenyl group, an alkoxy group with 1 to 6 carbon atoms, a phenylalkyl group with 1 to 6 carbon atoms in the alkyl, an alkyl group with 1 to 6 carbon atoms and an alkylthio group with 1 to 6 carbon atoms, the five latter radicals being optionally substituted and the aliphatic carbon structure of the three latter radicals being interrupted by one or more, identical or different, heteroatoms from the group comprising oxygen and sulfur, or R ¹⁵ and R ¹⁶ form with the carbon atom carrying them a three- to six-membered ring, which optionally contains one or two, identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is optionally substituted by one or more, identical or different radicals from the group consisting of a halogen atom, an alkyl group with 1 to 4 carbon atoms and a haloalkyl group with 1 to 4 carbon atoms. 3. Substituted 2,4-diamino-1,3,5-triazines of the general formula I according to claim 1 or 2, in which Aryl denotes a monocyclic or bicyclic aromatic radical with 5 to 10 ring atoms, of which 1, 2, 3 or 4 may independently be derived from the group consisting of oxygen, sulfur and nitrogen, optionally substituted by one • · - 156 or more, identical or different radicals from the group consisting of a halogen atom, a hydroxyl group, an amino group, a formyl group, an alkoxycarbonyl group with 1 to 4 carbon atoms in the alkoxyl group, an alkylcarbonyl group with 1 to 4 carbon atoms in the alkyl group, a haloalkoxycarbonyl group with 1 to 4 carbon atoms in the alkoxyl group, a haloalkylcarbonyl group with 1 to 4 carbon atoms in the alkyl group, an alkyl group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, an alkoxyalkyl group with 1 to 4 carbon atoms in both the alkyl and alkoxyl groups, a haloalkoxyalkyl group with 1 to 4 carbon atoms in both the alkyl and alkoxyl groups, a haloalkoxy-haloalkyl group with 1 to 4 carbon atoms in alkyl and alkoxy, alkoxy-haloalkyl group with 1 to 4 carbon atoms in alkyl and alkoxy, cycloalkyl group with 3 to 6 carbon atoms, cycloalkylalkyl group with 3 to 6 carbon atoms in cycloalkyl and with 1 to 4 carbon atoms in alkyl, cycloalkyl-haloalkyl group with 3 to 6 carbon atoms in cycloalkyl and with 1 to 4 carbon atoms in alkyl, halocycloalkyl-haloalkyl group with 3 to 6 carbon atoms in cycloalkyl and with 1 to 4 carbon atoms in alkyl, halocycloalkylalkyl group with 3 to 6 carbon atoms in cycloalkyl and with 1 to 4 carbon atoms in alkyl, alkylamino group and dialkylamino group with 1 to 6 carbon atoms in each alkyl, alkylaminocarbonyl group with 1 to 6 carbon atoms in each alkyl atoms in the alkyl, aminosulfonyl group, alkylaminosulfonyl and diallylaminosulfonyl groups with 1 to 6 carbon atoms in each alkyl, haloalkyl • · - 157 - • · · · · • · · · group with 1 to 4 carbons atoms and haloalkoxy- group with 1 to 4 carbons atoms, denotes a divalent unit of groups including -0- -S-, -NR ¹¹ - , -co ₂ -, -S0-, -SC ₂ -, -S0 ₂ 0- and -SO ₂ NR ¹⁴ -, -NH-CO-NH-, -OCONH-, -O-NH-, and -O-CH ₂ CH ₂ -0- , or trivalent unit -0-N= , -i J R and R each independently represent a residue of the group G5, comprising a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, a cycloalkoxy group with 3 to 6 carbon atoms, an arylalkyl group with 1 to 6 carbon atoms in the alkyl and a cycloalkylalkyl group with 3 to 6 carbon atoms in the cycloalkyl and with 1 to 6 carbon atoms in the alkyl, wherein the cyclic parts of the four latter-mentioned residues are optionally substituted by one or more, the same or different residues from the group comprising a halogen atom, a nitro group, a cyano group and a group -BX ¹ , wherein -B- and X ¹ are defined below and wherein the non-cyclic parts of the eight latter-mentioned residues of the group G5 are optionally substituted by one or more, the same or different residues from the group comprising a halogen atom, nitro group, cyano group and -BX group, wherein -B and X are defined below and wherein the non-cyclic parts of the residues of group G5 may be interrupted by one or more, identical or different, heteroatoms from the group comprising oxygen atom and sulfur atom, or • · - 158 ΊΟ Ί Ο R ³ · and R^ groups (CR R ) form with the carbon atom bearing it a carbonyl group, a CR ¹³ R ^1d group or a three- to six-membered ring which optionally contains one or two, the same or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted with up to four, the same or different radicals from the group comprising halogen atom, nitro group, cyano group and -BX ¹ group, or 1 19 two R of two directly or indirectly adjacent groups (CR R ) form together with the carbon atoms carrying them, or connecting them, an optionally substituted three- to six-membered ring, which optionally contains one or two identical or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by up to four identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX ¹ group, or 1 19 two R· ¹ · of two directly adjacent groups (CR R ) together with the bond between the carbon atoms of the groups indicates a double -i 9 bond or two R and two R of two directly adjacent groups (CR R ) together with the bond between the carbon atoms of the groups denotes a triple bond, or R ¹ denotes the binding site for the double bond in the case where About Y denotes the trivalent unit =N-0- adjacent to the CR R group, R ³ , R ⁴ each independently of one another denote a residue of the group G6, comprising a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms* · m ··· ·· ·· alkoxy group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkoxy group with 3 to 8 carbon atoms, an aryl group, an arylalkyl group with 1 to 4 carbon atoms in the alkyl, an arylalkoxy group with 1 to 4 carbon atoms in the alkoxy, a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 4 carbon atoms in the alkyl, a cycloalkylalkoxy group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 4 carbon atoms in the alkoxy, a cycloalkoxyalkyl group with 3 to 8 carbon atoms in the cycloalkoxy and with 1 to 4 carbon atoms in the atoms in the alkyl and a cycloalkoxyalkoxy group with 3 to 8 carbon atoms in the cycloalkoxy and with 1 to 4 carbon atoms in the alkoxy, wherein the cyclic part of the nine latter-named radicals is optionally substituted by one or more, the same or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX ¹ group, wherein -B- and X ¹ are defined below and wherein the non-cyclic part of the thirteen latter-named radicals of the group G6 is optionally substituted by one or more, the same or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX 1 group, wherein X is defined below and wherein the non-cyclic part of the radicals of the group G6 may be interrupted by one heteroatom from the group comprising oxygen and sulfur, or R ³ and R ⁴ form with the carbon atom carrying them a carbonyl group, a CR ¹³ R ^1b group or a three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by up to four identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX ⁴ group, or α and λ two R ^and two directly or indirectly adjacent groups (CR ^J R ) together with the carbon atoms carrying them, optionally connecting them, form an optionally substituted three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by up to four identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX ⁴ group, or two R ^J of adjacent groups (CR ^J R ) together with the bond between the carbon atoms of the groups form a double bond, or two R ⁴ and two R ⁴ of two directly adjacent groups (CR ² R ⁴ ) together with the bond between the carbon atoms of the groups form a triple bond, or also a R denotes the binding site for the double bond in the case where Y denotes the trivalent unit -0-N= adjacent to the CR ² R ⁴ group, -B- denotes a direct bond or a divalent unit from the group consisting of -0-, -S-, -NR ⁴⁴ -, -CO-, -CO2-, -S0-, -S0 ₂ - and -S0 ₂ NR ¹⁴ - , X ⁴ represents a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms or a heterocyclyl group with 3 to 6 atoms • · - 161 rings, of which 1, 2 or 3 are derived from the group consisting of nitrogen, oxygen and sulfur atoms and wherein the five latter radicals are optionally substituted by up to five identical or different halogen atoms, X represents a hydrogen atom or a heterocyclyl group with 3 to 6 ring atoms, of which 1, 2 or 3 are from the group consisting of nitrogen, oxygen and sulfur, optionally substituted by 1, 2 or 3 identical or different halogen atoms, R ³ , r 6 independently represent the residue of the group G 6 , or R and R of two directly or indirectly adjacent groups (CR ³ R ⁴ ) or (CR ³ R^) together with the carbon atoms connecting them form an optionally substituted three- to six-membered ring, which optionally contains one or two, identical or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by up to four identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a -BX ⁴ group, or R ³ and R^ with the supporting carbon atom form a carbonyl group, a CR^R^ group or a three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group comprising oxygen, nitrogen and sulphur and which is optionally substituted by one or more, the same or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, a thiocyanato group and a -Β-χ1 group, or R ⁶ represents a heterocyclyl group, • · • · - 162 R ⁷ denotes a hydrogen atom, an amino group, an alkylcarbonyl, alkylamino or dialkylamino group with 1 to 4 carbon atoms in each alkyl radical or an acyclic or cyclic hydrocarbon radical with 1 to 6 carbon atoms, each of the five latter radicals being optionally substituted by one or more identical or different radicals from the group comprising a halogen atom, an alkoxy group with 1 to 4 carbon atoms, a haloalkoxy group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, an alkenyloxy group with 2 to 4 carbon atoms, an alkynyloxy group with 2 to 4 carbon atoms, a hydroxy group, an amino group, an alkylamino and dialkylamino group with 1 to 4 carbon atoms in each alkyl radical, a nitro group, a carboxy group, cyano group, alkoxycarbonyl group with 1 to 4 carbon atoms in alkoxy, alkylcarbonyl group with 1 to 4 carbon atoms in alkyl, formyl group, carbamoyl group, alkylsulfonyl group with 1 to 4 carbon atoms and haloalkylsulfonyl group with 1 to 4 carbon atoms and in the case of cyclic radicals also alkyl group with 1 to 4 carbon atoms and haloalkyl group with 1 to 4 carbon atoms, O R denotes an alkyl group with 1 to 6 carbon atoms, which is optionally substituted by one or more, identical or different, radicals from the group consisting of a halogen atom, a cyano group, a hydroxy group, an alkoxy group with 1 to 4 carbon atoms, an alkylthio group with 1 to 4 carbon atoms, an alkylsulfonyl group I · · · 163 • · · · with 1 to 4 carbon atoms, the alkenyl group is 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, a phenyl group, a cycloalkyl group with 3 to 9 carbon atoms and a cycloalkoxy group with 3 to 9 carbon atoms and further denotes a cycloalkyl group with 3 to 8 carbon atoms or a cycloalkoxy group with 3 to 8 carbon atoms, the latter two radicals being optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group, an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, a haloalkyl group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, R ⁹ , R ⁴⁹ independently represent a hydrogen atom, an amino group, an alkylcarbonyl group with 1 to 4 carbon atoms in the alkyl, an alkylamino group with 1 to 4 carbon atoms, a dialkylamino group with 1 to 4 carbon atoms in each alkyl, an alkyl group with 1 to 4 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, a cycloalkoxy group with 3 to 8 carbon atoms or a heterocyclyl group with 3 to 6 ring atoms and 1 to 3 ring heteroatoms from the group consisting of oxygen, nitrogen and sulfur, each of the eight latter radicals being optionally substituted by one to four, identical or different radicals from the group consisting of a halogen atom, an amino group, a hydroxy group and, in the case of cyclic radicals, also an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, haloalkyl• · - 164 a haloalkyl group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, or R ⁹ and R 10 together with the nitrogen atom carrying them form a heterocycle with a total of three to six ring atoms and one to four ring heteroatoms, where in addition to the nitrogen atom present, there are optionally further ring heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, and this heterocycle is optionally substituted, R ⁴⁴ denotes a hydrogen atom, an amino group, an alkylamino group with 1 to 4 carbon atoms, a dialkylamino group with 1 to 4 carbon atoms in each alkyl, an alkyl group with 1 to 4 carbon atoms, a cycloalkyl group with 3 to 8 carbon atoms, a cycloalkylalkyl group with 3 to 8 carbon atoms in the cycloalkyl and with 1 to 4 carbon atoms in the alkyl, an alkoxy group with 1 to 4 carbon atoms, an alkoxyalkoxy group with 1 to 4 carbon atoms in each alkoxy, a cycloalkoxy group with 3 to 8 carbon atoms and an alkylcarbonyl group with 1 to 4 carbon atoms in the alkyl, the nine latter radicals being optionally substituted by one or more identical or different halogen atoms and, in the case of cyclic radicals, also by an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, a haloalkyl group with 1 to 4 carbon atoms and a haloalkoxy group with 1 to 4 carbon atoms, R ⁴⁴ represents a hydrogen atom or optionally one or more, identical or different, radicals from the group consisting of a halogen atom, an alkoxy group with 1 to 4 carbon atoms, 165 atoms and a haloalkoxy group with 1 to 4 carbon atoms substituted by an alkyl group with 1 to 4 carbon atoms or a cycloalkyl group with 3 to 6 carbon atoms, aryl5, ^R4-6 independently of one another denotes a hydrogen atom, a phenyl group, an alkoxy group with 1 to 4 carbon atoms, a phenylalkyl group with 1 to 4 carbon atoms in the alkyl, an alkyl group with 1 to 4 carbon atoms and an alkylthio group with 1 to 4 carbon atoms, the five latter radicals being optionally 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 comprising a halogen atom, an alkyl group with 1 to 4 carbon atoms and a haloalkyl group with 1 to 4 carbon atoms, or 1 S 1 A R ^±J and R ^XD form with the carbon atom bearing them a three- to six-membered ring, which optionally contains one or two, the same or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is optionally substituted with up to four, the same or different radicals from the group consisting of a halogen atom, an alkyl group with 1 to 4 carbon atoms and a haloalkyl group with 1 to 4 carbon atoms. 4. Substituted 2,4-diamino-1,3,5-triazines of general formula I according to claim 1 to 3, in which Aryl means phenyl, naphthyl, pyridinyl, pyrimidinyl, furanyl, benzofuranyl, pyrrolyl, 166 oxazolyl, thiazolyl, imidazolyl, oxadiazolyl or thienyl group, which are optionally substituted by one or more, identical or different radicals from the group comprising a halogen atom, a hydroxy group, an amino group, a formyl group, an alkoxycarbonyl group with 1 to 4 carbon atoms in the alkoxy, an alkylcarbonyl group with 1 to 4 carbon atoms in the alkyl, an alkyl group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, an alkylamino group and a dialkylamino group with 1 to 4 carbon atoms in each alkyl, an aminocarbonyl group, an alkylaminocarbonyl and a dialkylaminocarbonyl group with 1 to 4 carbon atoms in each alkyl, an aminosulfonyl group, an alkylaminosulfonyl and a diallylaminosulfonyl group with 1 to 4 carbon atoms in each alkyl, a haloalkyl group with 1 to 4 carbon atoms, a haloalkoxy group with 1 to 4 carbon atoms, an alkylthio group with 1 to 2 carbon atoms, an alkylsulfinyl group with 1 to 2 carbon atoms, an alkylsulfonyl group with 1 to 2 carbon atoms, a haloalkylthio group with 1 to 2 carbon atoms, a haloalkylsulfinyl group with 1 to 2 carbon atoms and a haloalkylsulfonyl group with 1 to 2 carbon atoms, —Y— denotes a divalent unit from the group consisting of —O—, -S-, -NR ¹¹ -, -C0 ₂ -, -S0-, -S0 ₂ -, -NH-CO-NH-, -OCONH-, -O-NH- and -O-CH ₂ CH ₂ -O- , or the trivalent unit -0-N= , m denotes the number 0, 1, 2 or 3, • · - 167 n stands for the number 1, 2, 3, 4 or 5, R and R each independently denote a residue of the group G7, comprising an alkyl group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, a hydrogen atom or a cycloalkyl group with 3 to 6 carbon atoms, the latter residue being optionally substituted by up to four identical or different residues from the group comprising a halogen atom and a group -BX ³ and the four first-mentioned residues of the group G7 being optionally substituted by one or more identical or different residues from the group comprising a halogen atom and a group -ΒΧ , wherein -B and X are defined below, or Ί 9 19 The R and R groups (CR R ) form a carbonyl group with the carbon atom bearing them, or Ί 19 two R of two directly or indirectly adjacent groups (CR R ) form together with the carbon atoms carrying them, or connecting them, a three-membered, five-membered or six-membered ring, optionally substituted with up to four identical or different residues from the group comprising a halogen atom and a group -Β-Χ^ , which may contain up to 2 heteroatoms from the group comprising oxygen, sulfur and nitrogen, or R ⁴ indicates the binding site for the double bond in the case where 1 2 Y denotes the trivalent unit =N-0- adjacent to the CR R group, « · ♦ * • · · 168 R ³ , R ⁴ each independently of one another denote a residue of the group G8, comprising a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, a cycloalkoxy group with 3 to 6 carbon atoms, an aryl group, an arylalkyl group with 1 to 2 carbon atoms in the alkyl, an arylalkoxy group with 1 to 2 carbon atoms in the alkoxyl, a cycloalkylalkyl group with 3 to 6 carbon atoms in the cycloalkyl and with 1 to 2 carbon atoms in the alkyl, a cycloalkoxyalkylol group with 3 to 8 carbon atoms in the cycloalkoxy and with 1 to 4 carbon atoms in the alkyl, the cyclic part of the seven latter radicals being optionally substituted with up to four identical or different radicals from the group comprising a halogen atom, a nitro group, a cyano group and a group -BX ¹ , wherein -Ba and X ¹ are defined below and wherein the non-cyclic part of the eleven latter-named residues of the group G8 is optionally substituted by one or more, identical or different residues from the group comprising a halogen atom, a nitro group, a cyano group and a group -BX 9 , wherein X is defined below, or R ³ and R ⁴ groups (CR ³ R ⁴ ) form a carbonyl group with the carbon atom carrying them, or two R ³ of two directly or indirectly adjacent groups (CR ^J R) form a three-, five- or six-membered ring with the carbon atoms carrying them, or connecting them, optionally substituted with up to four identical or different radicals from the group comprising a halogen atom 169 and the group -BX ⁴ , which may contain up to 2 heteroatoms from the group including oxygen, sulfur and nitrogen, or denotes a binding site for a double bond in the case where Y denotes a trivalent unit -O-N= adjacent to the group CR ² R ⁴ , -B- denotes a direct bond or a divalent unit from the group consisting of -O-, -S-, -NR ⁴⁴ -, -CO- and -C0 ₂ -, X ⁴ denotes a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms or a cycloalkyl group with 3 to 6 carbon atoms, the four latter radicals being optionally substituted by up to five identical or different halogen atoms, X represents a hydrogen atom or a heterocyclyl group with 3 to 6 ring atoms, of which 1, 2 or 3 are from the group consisting of nitrogen, oxygen and sulfur, optionally substituted by one or more identical or different halogen atoms, R^ represents a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, a haloalkyl group with 1 to 4 carbon atoms or a cycloalkyl group with 3 to 6 carbon atoms, 7 S R and R of two directly or indirectly adjacent groups (CR ² r4) or (CR^R^) together with the carbon atoms connecting them form optionally up to four identical or different radicals from the group comprising the atom - 170 • · < • · · • * · • · * · halogen and the group -BX ⁴ substituted three-, five- or six-membered ring, which optionally contains up to two heteroatoms from the group comprising oxygen, nitrogen and sulfur, r6 denotes a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, an alkenyl group with 2 to 4 carbon atoms, an alkynyl group with 2 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, a cycloalkylalkyl group with 3 to 6 carbon atoms in the cycloalkyl and with 1 to 4 carbon atoms in the alkyl, a cycloalkoxyalkyl group with 3 to 6 carbon atoms in the cycloalkyl and with 1 to 4 carbon atoms in the alkyl, a cycloalkoxy group with 3 to 6 carbon atoms, an alkoxyalkyl group with 1 to 4 carbon atoms in both alkyl and alkoxy or a haloalkyl group with 1 to 4 carbon atoms, R represents a hydrogen atom, an amino group or an alkyl group with 1 to 4 carbon atoms, O R represents an alkyl group with 1 to 4 carbon atoms, a cycloalkyl group with 3 to 6 carbon atoms, a halocycloalkyl group with 3 to 6 carbon atoms or a cycloalkylalkyl group with 3 to 6 carbon atoms in the cycloalkyl and 1 to 4 carbon atoms in the alkyl, R ⁹ , R ⁴⁹ independently represent a hydrogen atom, an amino group, a formyl group or an alkyl group with 1 to 4 carbon atoms, or 171 R ⁹ and R ¹⁰ together with the nitrogen atom carrying them form a heterocycle with a total of three to six ring atoms and one to two ring heteroatoms, where in addition to the nitrogen atom present, any other ring heteroatoms are selected from the group consisting of oxygen and nitrogen. R ⁴⁴ represents a hydrogen atom, an amino group, an alkylamino group with 1 to 4 carbon atoms, a dialkylamino group with 1 to 4 carbon atoms in each alkyl, an alkyl group with 1 to 4 carbon atoms or a cycloalkyl group with 3 to 6 carbon atoms, the five latter radicals being optionally substituted by one or more identical or different halogen atoms and R ⁴⁴ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 5. A process for the production of substituted 2,4-diamino-1,3,5-triazines of the general formula I or their salts, according to any one of claims 1 to 4, characterized in that a) react the compound of general formula II R ⁸ - Fu (II), in which it denotes a functional group from the group including carboxylic acid esters, orthoesters of carboxylic acidsFu - 172 lin, carboxylic acid chlorides, carboxylic acid amides, carboxylic acid anhydrides and a trichloromethyl group, with a biguanide of general formula III or its acid addition salt Aryl-(CR ¹ _R \ - Y - (ClþR ⁴ ),, - CR ⁵ - NR ⁷ -U- N -IL NR ⁹ R ¹ ° (HI) or se b) react the compound of general formula IV ^X NR ¹ ° N= ^ζ 'Λ j' N—( (IV) in which denotes an exchangeable residue or a leaving group, for example a chlorine atom, a trichloromethyl group, an alkylsulfonyl group with 1 to 4 carbon atoms and an unsubstituted or substituted phenylalkylsulfonyl or alkylphenylsulfonyl group with 1 to 4 carbon atoms in the alkyl, with a suitable amine of the general formula V or its acid addition salt • · ^R5 Aryl—(CR ¹ R ² )—Y—(CR ³ r\—CR ⁵ —NHR ⁷ ( ⁷ ) wherein in formulas II, III, IV and V the radicals R^ to rIO and Y and anam have the meanings given in formula I . 6. Herbicidal composition or plant growth regulating composition, characterized in that it contains one or more compounds of the general formula I or their salts according to any one of claims 1 to 4, optionally in a mixture with formulation auxiliaries. 7. A method for controlling unwanted plants or regulating plant growth, characterized in that an effective amount of one or more compounds of the general formula I or their salts according to any one of claims 1 to 4 or a composition according to claim 6 is applied to plants, to the place where unwanted plants grow or to the growing area. 8. Use of compounds of the general formula I or their salts according to any one of claims 1 to 4 or herbicidal compositions according to claim 6 for controlling unwanted plants or for regulating plant growth. 9. Use according to claim 8, in which the compounds of general formula I or their salts are used for controlling unwanted plants or for regulating plant growth in crops of useful plants. 10. Use according to claim 9, wherein the useful plants are transgenic useful plants.