MXPA00012730A

MXPA00012730A - Substituted 2,4-diamino-1,3,5-triazines, methods for the production thereof and their use as herbicides and plant growth regulators

Info

Publication number: MXPA00012730A
Application number: MXPA/A/2000/012730A
Authority: MX
Inventors: Lothar Willms; Thomas Auler; Christopher Rosinger; Hermann Bieringer; Jens Hollander; Jurgen Zindel; Klemens Minn; Wolfgang Giencke
Original assignee: Aventis Cropscience Gmbh
Priority date: 1998-06-26
Filing date: 2000-12-18
Publication date: 2002-07-25

Abstract

The invention relates to substituted 2,4-diamino-1,3,5-triazines of general formula (I) and to the salts thereof. The invention also relates to methods for the production of the substituted triazines and to their use as herbicides and plant growth regulators. In general formula (I), R1 to R10 represent different radicals, Y represents a divalent unit, aryl represents an optionally substituted aromatic radical, m is a number from 0 to 5, and n is a number from 1 to 10.

Description

2. 4-PIAMINO-1.3.5-SUBSTITUTE TRIAZINES. METHODS FOR THE PRODUCTION OF THEM AND THEIR USE AS HERBICIDES AND REGULATORS OF PLANT GROWTH FIELD OF THE INVENTION The invention relates to the technical area of herbicides and plant growth regulators, in particular to that of herbicides for the selective control of broadleaf weeds and weedy grasses in crops of useful plants.

BACKGROUND OF THE INVENTION It is already known from several publications that certain 2,4-diamino-1, 3,5-triazines have herbicidal properties. Thus, WO 97/00254 describes 2,4-d-amino-1, 3,5-triazines carrying a phenyl radical linked to an amino group by a chain of ethylene, oxyethylene, aminoethylene, thioethylene or propylene. WO 97/08156 describes 2,4-diamino-1, 3,5-triazines in which a phenyl radical is linked to an amino group by an alkylene, alkenylmethyl or alkynylenemethyl chain. WO 98/15537 describes 2,4-diamino-1, 3,5-triazines carrying an aromatic or heterocyclic radical linked by a propylene or oxyethylene chain to an amino group. Finally, WO 98/15539 i? * t ** . ? .....,. . . - ..,. - * * *. -. » «. -,] Jt1í_j_j_ ^ jfJ3fLjj f_ mentions 2,4-diamino-1, 3,5-triazines bearing a benzyl, naphthylmethyl, heterocyclyl or heterocyclyloxy radical linked by a chain of ethylene to an amino group. However, in practice, the use of the 2,4-diamino-1, 3,5-triazines known from these publications often entails disadvantages. In this way, the herbicidal or growth regulating activity of the plants of the known compounds is not always sufficient or, when the herbicidal activity is sufficient, undesirable damage is observed to the crop plants. 10 DESCRIPTION OF THE INVENTION An object of the present invention is to provide herbicidal compounds and plant growth regulators, which overcome the known disadvantages of the prior art. The objective is met by means of 2,4-diamino-1, 3,5-triazines of formula I, if appropriate also in the form of their salts, in which inri 'ii Üm + Mi? c i r f i. I IIÉMÉIII i i. íl im ni ^ i ^ tm **? i * ^ * * -? ^^^^^ I ^^^ * ^^^^^ * m ^? íÍ * ^^ Aril is a radical mono- or substituted or unsubstituted bicyclic aromatic having from 5 to 14 ring atoms, 1, 2, 3 or 4 of which can, in each case independently of one another, originate from the group consisting of oxygen, sulfur and nitrogen; Y-Y is a divalent unit of the group consisting of -O-, -S-, -NR11-, -NR 2CONR13-, -C02-, -OC02-, -OCONR14-, -SO-, -S02-. -S020-, - OS020-, -S02NR14-, -O-NR 1, -NR'-NR "-, in which R 'and R", independently of one another, are as defined for R14, and - ( Y'-CRaRb- CRcR); - Y ", where Y 'and Y" are, independently of one another, O, S, NH or CrN N-chloro], Ra, Rb, Rc and Rd are in each case, independently of each other, H or alkyl of C -.- C, ei is an integer of 1 to 5, preferably 1, or a trivalent unit of formula -0-N =; m is 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2 or 3; n is an integer from 1 to 10, preferably from 1 to 5, in particular 1, 2, 3 or 4, with the proviso that n is not 1 if m is zero and -Y- is - O-, -S -, -SO-, -S02- or -NR11-; R, R2 in each case, independently of one another, is a radical of a group G1 comprising hydrogen, C 1 -C 0 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, CiC-1 alkoxy, C3-C8 cycloalkyl, C3-C8 cycloalkoxy, Ci-C3 arylalkyl and (C3-C8) cycloalkyl Ci-C3 alkyl, wherein the cyclic portion of the last four mentioned radicals is unsubstituted in each case or is substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X1, wherein - B- and X1 are as defined below, and wherein the non-cyclic portion of the last eight mentioned radicals of the group G1 is, in each case, unsubstituted or substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X2, wherein X2 is 5 as defined below, and wherein the non-cyclic portion of the radicals of the group G1 may, in each case, be interrupted with one or more heteroatoms identical or different from the group consisting of oxygen and sulfur, or R1 and R2 of a group (CR1R2) form together with the The carbon carrying a carbonyl group, a CR15R16 group or a 3-6 membered ring which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X1, or two R1 of two groups (CR1R2) directly adjacent or not directly adjacent, together with the carbon atoms that the carry or link them, form an unsubstituted or substituted 3 to 6 membered ring which may contain one or two heteroatoms different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X1, or two R1 of two groups (CR1R2) directly adjacent, together with the bond between the carbon atoms of the groups, they form a double bond, or two R1 and two R2 of two groups (CR1R2) directly adjacent, together with the bond between the carbon atoms of the groups, form a triple bond, or R1 is a point of attachment for the double bond in the in which case Y is a trivalent unit = NO- adjacent to a group CR1R2, R3, R4 in each case, independently of one another, is a radical of a group G2 comprising hydrogen, C1-C10 alkyl, C2 alkenyl -C8, C2-C8 alkynyl, C1-C10 alkoxy, C1-C10 alkylthio, C?-C10 alkylsulfinyl, C -.- C10 alkylsulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkoxy, aryl, C -? - C6 arylalkyl, Ci-C? arylalkoxy, (C3-C8) cycloalkyl-CrC6 alkyl, (C3-C8) cycloalkyl-C6-C6-alkoxy, (C3-C8) cycloalkoxy-Ci alkyl -Cd and (C3-C8) cycloalkoxy-CrC6 alkoxy, wherein the cyclic portion of the last nine mentioned radicals, in each case, is not substituted or is substituted with one or more identical or different radicals of the group q which consists of halogen, nitro, cyano, thiocyanate and -B-X1, wherein -B- and X1 are as defined below, and wherein the non-cyclic portion of the last sixteen mentioned radicals of the group G2, in each case is unsubstituted or is substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X2, wherein X2 is as defined below, and wherein the non-cyclic portion of the radicals of the group G2 can be, in each case, interrupted by one or more heteroatoms identical or different from the group consisting of oxygen and sulfur, or R3 and R4 together with the carbon atom that bears them, form a carbonyl group, a CR15R16 group or a 3 to 6 member ring, which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or is substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X1, or * two R3 of two groups (CR3R4) directly adjacent or not directly adjacent, together with the The carbon carrying or linking them forms a 3 to 6 membered unsubstituted or substituted ring, which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted. is substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X1; or two R3 of two groups (CR3R4) directly adjacent, together with the bond between the carbon atoms of the groups, form a double bond, or two R3 and two R4 of two groups (CR3R4) directly adjacent, together with the bond between the carbon atoms of the groups, form a triple link, or R3 is a point of attachment for the double bond in the case at ^ 20 that Y is a trivalent unit -0-N = adjacent to a group CR3R4, -B- is a direct link or a divalent unit of the group consisting of -O-, -S-, -NR11-, -NR12C0NR13-, -C02-, -OC02-, -OCONR14-, -SO-, -S02-, -S020-, -OS020-, and- S02NR14-; nhfwnt-ffttif • Í • t, Aái ^ - ^^^ - ^^^^^^^^^^^^^^^ X1 is hydrogen, C -? - C8 alkyl, C2-C8 alkenyl, alkynyl of C2-C8, C3-C8 cycloalkyl or heterocyclyl having from 3 to 9 ring atoms, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen and sulfur, and wherein the last five radicals 5 mentioned are not substituted or are substituted with one or more identical or different halogen atoms; X2 is hydrogen or heterocyclyl having from 3 to 9 ring atoms, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen and sulfur, which is unsubstituted or substituted by one or more other hydrogen atoms. halogen identical or different; R5, R6 each, independently of one another, is a radical of the group G2, or R3 and R5 of two groups (CR3R4) or (CR5R6), directly adjacent or not directly adjacent to each other, than with the carbon atoms which bind them they form an unsubstituted or substituted 3 to 6 membered ring which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more identical or different radicals of the group consisting of halogen, nitro, cyano, thiocyanate and -B-X1, or R5 and R6 together with the carbon atom that bears them, form a carbonyl group, a CR15R16 group or a 3 to 6 member ring that can contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or is not • - * • "* - -u- • - • • • - * - -1 - AdÉMáuhMtaaiaHiMi? ^^ MMiíMÉall ailllÉa • MM ^^ MHÉM substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X1, or R6 is heterocyclyl, R7 is hydrogen, amino, alkylcarbonyl, alkylamino or dialkylamino, which in each case has from one to six carbon atoms in the alkyl radical, is an acyclic hydrocarbon or hydrocarbonoxy radical which in each case has from one to six carbon atoms, is a cyclic hydrocarbon radical or hydrocarbonoxy having in each case from three to six carbon atoms or is heterocyclyl, heterocyclyloxy or heterocyclylamino having in each case from three to six carbon atoms. ring and one to three ring heteroatoms of the group consisting of nitrogen, oxygen and sulfur, wherein each of the last ten radicals mentioned is unsubstituted or is substituted with one or more radicals identical or different from the group consisting of halogen, C1-C4 alkoxy, halogen-C4 alkoxy, Cth-C4 alkylthio, C2-C4 alkenyl, C2-C4 alkynyl, C2-C4 alkenyloxy, C2-C alkynyloxy, hydroxyl , amino, acylamino, alkylamino, dialkylamino, nitro, carboxyl, cyano, azido, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, formyl, carbamoyl, mono- and dialkyl (C 1 -C 4) aminocarbonyl, alkylsulfinyl of C 1 -C 4 , C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, CiC haloalkylsulfonyl and, in the case of cyclic radicals, also C 1 -C 4 alkyl and C 1 -C 4 haloalkyl, R 8 is C 1 -C 10 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, which are unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, cyano, nitro, thiocyanate, hydroxyl, alkoxy, C -? - C4, C-C alkylthio, C1-C4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, phenyl, C3-Cg cycloalkyl, C3-Cg cycloalkoxy, and is heterocyclyl having from three to six a ring atoms and from one to three ring heteroatoms of the group consisting of oxygen, nitrogen and sulfur, which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, amino, C-alkyl ? -C, C1-C4 alkoxy, halo-C1-C4 alkyl and halo-C-1-C4 alkoxy, is C3-C8 cycloalkyl, C3-C8 cycloalkoxy or a heterocyclyl radical having from three to six ring atoms, wherein these last three mentioned radicals are unsubstituted or substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halo C 1 -C 4 alkyl and halo C 1 -C 4 alkoxy, R 9, R 10 each independently of one another, is hydrogen , amino, C 10 -C 10 alkylcarbonyl, C 1 -C 0 alkylamino, C 1 -C 10 dialkylamino, Ci-do alkyl, C 3 -C 8 cycloalkyl, C 10 alkoxy, C 3 -C 8 cycloalkoxy, heterocyclyl , heterocyclyloxy or heterocyclylamino having in each case from 3 to 6 ring atoms and from 1 to 3 ring heteroatoms of the group consisting of oxygen, nitrogen and sulfur, wherein each of the last ten radicals mentioned is not substituted or is substituted, or R9 and R10 together with the nitrogen atom that bears them, form a heterocycle having a total of three to six ring atoms, and aivm? - - r- & .- - • • • ÉM MIG -? t - • ¡t _ ^ - ^^^^^^^^^^^^ and ^^^^^^^^^^^^ ^^^^^ m ^ between these, one to four ring heteroatoms, wherein the other ring heteroatoms which may be present in addition to the nitrogen atom that is present, are selected from the group consisting of oxygen, nitrogen and sulfur, and wherein this heterocycle is unsubstituted or substituted, R11 is hydrogen, amino, C1-C10 alkylamino, C1-C10 dialkylamino, C1-C10 alkyl, C3-C8 cycloalkyl, (C3-C8) cycloalkyl-alkyl of CrC6, C1-C10 alkoxy, alkoxy (CrC6) -alkoxy of C -.- C6, cycloalkoxy of C3-C8, alkylcarbonyl of C1-C10, wherein the last nine mentioned radicals are unsubstituted or substituted, R12, R13 each, independently of one another, is hydrogen, C1-C10 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, phenylalkyl of Ci-Cß, cycloalkyl of C3-C8, cycloalkyl (C3-C8) -alkyl of C -.- C6, where the cyclic portion The last four mentioned radicals, in each case, is unsubstituted or substituted with one or more radicals identical or different from the group consisting of C 1 -C 4 alkyl, halo C 1 -C 4 alkyl, C 1 -C 4 alkoxy and halo-C1-C4 alkoxy, or R12 and R13 together with the N-CO-N group that bears them, form a ring of 5 to 8 members which, in addition to the two nitrogen atoms mentioned above, can contain a heteroatom additional of the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted, Háta aaMMÉMatt t ** * AlHMIiail R14 is hydrogen or C-C10 alkyl or C3-C10 cycloalkyl, unsubstituted or substituted in each case, R15, R16 independently of one another, is hydrogen, aryl, C1 alkoxy -C10, arylalkyl of C -.- C6, alkyl of C1-C10, alkylthio of Cr C10, wherein the last five mentioned radicals are unsubstituted or substituted, and wherein the skeleton of aliphatic carbon of the last three radicals mentioned may be interrupted by one or more heteroatoms identical or different from the group consisting of oxygen and sulfur, or R15 and R6 together with the carbon atom carrying them, form a 3-6 membered ring which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted. The term "aryl" is understood to mean, for example, phenyl, naphthyl, biphenyl, tetrahydronaphthyl, indenyl, adenyl, pentalenyl, fluorenyl, aziridinyl, azetidinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, thiazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, oxazinyl, thiazinyl, thiadiazinyl, oxadiazinyl, dithiazinyl, thioxazinyl, indolyl, benzoxazolyl, benzothiazolyl, quinolinyl, isoquinolinyl, cinolinyl, quinazolinyl, purinyl or naphthyridinyl. These aryl radicals can, in principle, if the structure of the ring system allows it, be attached to the remaining portion of the molecule of the compound of formula I, at any position of the aryl radical.

^ ^ ^^ If -Y- or -B- is an asymmetric divalent unit, that is, if there are two options for joining, in each case both options for the union of -Y- or -B- with the rest of the molecule on the other side, are encompassed by the formula I. In formula I and in all subsequent formulas, the carbon-containing radicals, such as alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio, and the corresponding radicals which are nsaturated and / or substituted in the carbon skeleton, such as alkenyl and alkynyl, can, in each case, be straight or branched chain. Unless specifically mentioned otherwise, for these radicals the lower carbon skeletons are preferred, for example, those having 1 to 6 carbon atoms or in the case of unsaturated groups, those having 2 to 4 carbon atoms. of carbon. Alkyl radicals, including in compound meanings such as alkoxy, haloalkyl, etc., are for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyl as n -hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; the alkenyl and alkynyl radicals have the meanings of the possible unsaturated radicals corresponding to the alkyl radicals; alkenyl, for example, is allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl; Alkynyl, for example, is propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. The multiple bond can be in any position of the unsaturated radical.

J ^ a «« MMtMMMBIMMiiMtiHt ^ Éááitafliii Cycloalkyl is a carbocyclic saturated ring system having from three to nine carbon atoms, for example, cyclopropyl, cyclopentyl or cyclohexyl. In the case of compound radicals such as (C3-C8) cycloalkyl-C-i-C3 alkyl, the first mentioned radical may be in any position of the second mentioned radical. In the case of a doubly substituted amino group, such as dialkylamino, these two substituents may be identical or different. Halogen is fluorine, chlorine, bromine or iodine. Halo-alkyl, -alkenyl and -alkynyl, are alkyl, alkenyl or alkynyl which are partially or completely substituted with halogen, preferably with fluorine, chlorine and / or bromine, in particular with fluorine or chlorine, for example, CF3, CHF2, CH2F, CF3CF2, CH2FCHCI, CCI3, CHCI2, CH2CH2CI; haloalkoxy is for example OCF3, OCHF2, OCH2F, CF3CF20, OCH2CF3 and OCH2CH2CI; this applies correspondingly to halo-alkenyl and other halogen-substituted radicals. An acyl radical is the radical of an organic acid, for example the radical of a carboxylic acid and acid radicals derived therefrom, such as thiocarboxylic acid, unsubstituted or N-substituted iminocarboxylic acids, or the carbon monoester radical, acid unsubstituted or N-substituted carbaminic, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids. Acyl is, for example, formyl, alkylcarbonyl such as C-C - alkylcarbonyl, phenylcarbonyl, wherein the phenyl ring is unsubstituted or substituted, for example as shown above for phenyl, or alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl or other organic acid radicals. A hydrocarbon radical is a saturated or unsaturated, straight-chained, branched or cyclic aliphatic hydrocarbon radical, or an aromatic hydrocarbon radical; for example, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl and fluorenyl. Substituted radicals, such as substituted hydrocarbon radicals, for example alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, or substituted heterocyclyl, are for example a radical derived from the parent compound and which is substituted with one or more other radicals identical or different, the substituents being, for example, one or more, preferably, unless otherwise mentioned, 1, 2 or 3 radicals of the group consisting of halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino such as acylamino, mono- and dialkylamino and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl and, in the case of cyclic radicals, also alkyl and haloalkyl, and unsaturated aliphatic radicals corresponding to the above-mentioned saturated hydrocarbon-containing radicals, such as alkeni it, alkynyl, alkenyloxy, alkynyloxy, etc. Preferred radicals with carbon atoms are those with up to 4 carbon atoms. Preference is usually given to substituents of the group consisting of halogen, for example fluorine and chlorine, C 1 -C 4 alkyl, preferably methyl or ethyl, halo C 1 -C 4 alkyl, preferably trifluoromethyl, C 1 -C 4 alkoxy, preferably methoxy or ethoxy, halo-C1-C4 alkoxy, nitro and cyano. Particular preference is given here to the methyl, methoxy and chloro substituents. If the carbon chain of an alkyl, alkenyl or alkynyl radical is interrupted by more than one heteroatom, these heteroatoms will not be directly adjacent. Unless otherwise indicated, the term "heterocycle" means a saturated, unsaturated or heteroaromatic ring system containing one or more heteroatoms, preferably from the group consisting of oxygen, sulfur and nitrogen. Examples include pyridine, pyrimidine, pyridazine, pyrazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinoline, thiophene, thiazole, oxazole, oxetane, furan, pyrrole, pyrazole, imidazole, aziridine, oxirane, pyrrolidine, piperidine, piperazine, dioxolane, morpholine, tetrahydrofuran. The terms "heterocyclyl" and "heterocyclic radical" are also understood in this sense, that is, as radicals deriving from the heterocycles mentioned above. If a heterocycle contains at least two heteroatoms, the condition is applied that two oxygen atoms can not be directly adjacent. These heterocycles can, in principle, if the structure of the ring system allows it, be linked with the other portion of the molecule of the compound of formula I, at any position of the heterocycle. Unless indid otherwise, the heterocycle may be unsubstituted or substituted with one or more identical or different radicals.

MaMÉU feMattti A ^ U ^^ IMMIIHM These radicals can be the radicals mentioned under the "substituted hydrocarbon radicals", and additionally also oxo. The oxo group can also be present in the ring heteroatoms, which can exist in different oxidation states, for example in nitrogen and sulfur. A ring can be saturated, partially saturated, completely unsaturated or aromatic. The above-mentioned examples of radicals or ranges of radicals that are included in the general terms, such as "alkyl", "acyl", "substituted radicals", etc., are not considered as a complete list. The general terms also include the definitions of ranges of radicals in groups of preferred compounds listed below, in particular ranges of particular radicals that include the specific radicals of the examples in the tables. Depending on the type and the binding of the substituents, the compounds of formula I may be present as stereoisomers. If, for example, one or more alkenyl groups are present, this can lead to diastereomers. If, for example, one or more asymmetric carbon atoms are present, this can lead to enantiomers and diastereomers. The stereoisomers can be obtained from the resulting mixtures of the preparation, using customary preparation methods, for example chromatographic separation processes. The stereoisomers can also be selectively prepared using stereoselective reactions using optically active starting materials and / or auxiliaries. The invention . , k. i. . ? ,. . 1 »* < »- .. . . * > »« - .... m "M ^^^^^^^^^^ ß ^ j ^^^^ g¡ll¡? it also refers to all stereoisomers and their mixtures, which are encompassed by formula I although they are not specifically defined. The compounds of formula I also include tautomers of compounds that are formed by displacements of hydrogen, such as for example enols and others, even when said compounds do not formally correspond to formula I. Depending on the type of substituents, the compounds of formula I can form salts, and are encompassed by the term "compounds (of formula I)". In substituents with acidic properties, such as COOH and S03H, the hydrogen atom of the acid group can be replaced with an agriculturally suitable cation. These salts are, for example, metal salts, in particular, alkali metal salts or alkaline earth metal salts, in particular, sodium and potassium salts, or even ammonium salts, or salts with organic amines. Salt formation can also occur by the addition of an acid to basic substituents, such as, for example, amino and alkylamino. Acids which are suitable for this purpose are strong inorganic and organic acids, for example HCl, HBr, H2S04 or HNO3. Said salts also form part of the subject matter of the invention. It is understood that the possibilities of combining the different substituents of the formula I are such that the general principles of construction of chemical compounds are fulfilled, ie that no compounds are formed that are known to the person skilled in the art as chemically unstable or impossible.

-. «A ^ A ^. «.. ... ... - ... ,. .. t ... -, ._. »_., ...... ^ -. - ___________ - ^ - ^ "- ^ - ^ - ^ a" - * ^ Preference is given to the compounds of formula I and their salts in which: aryl is an unsubstituted or substituted mono- or bicyclic aromatic radical having from 5 to 10 ring atoms, 1, 2, 3 or 4 of which in each case independently of one another, can originate from the group consisting of oxygen, sulfur and nitrogen, and / or -Y- is a divalent unit of the a group consisting of -O-, -S-, -NR11-, -NR12CONR13-, -C02-, -OCONR14-, -SO-, -S02-. -S020-, -S02NR14-, -O-NR11, -NH-NH and -0-CRaRb-CRcRd-0-, wherein Ra, Rb, Rc and Rd are independently of each other, H, CH3 or C2H5, or well a trivalent unit of formula -0-N =, and / or R 1, R 2 are each independently of one another, a radical of a group G 3 comprising hydrogen, C 8 -C 8 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 alkoxy C6, C3-C8 cycloalkyl, C3-C8 cycloalkoxy, C6-C6 arylalkyl and (C3-C8) cycloalkyl Ci-C3 alkyl, wherein the cyclic portion of the last four radicals mentioned, in each case is unsubstituted or is substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X1, wherein -B- and X1 are as defined below, and wherein the non-cyclic of the last eight mentioned radicals of the group G3, in each case, is unsubstituted or is substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X2, wherein X2 is as defined below, and wherein the non-cyclical portion of the radicals of the In each case, it may be interrupted with one or more heteroatoms identical or different from the group consisting of oxygen and sulfur, or two R1 of two groups (CR1R2) directly adjacent to each other. with the bond between the carbon atoms of the groups, form a double bond, or two R1 and two R2 of two groups (CR1R2) directly adjacent, together with the bond between the carbon atoms of the groups, form a triple bond or R1 is a point of attachment for the double bond in the case in the that Y is a trivalent unit = N-0- adjacent to a group CR1R2, and / or R3 and R4 each, independently of one another, is a radical of a group G4 comprising hydrogen, C -.- C8 alkyl , C2-C6 alkenyl, C2-C6 alkynyl, C -.- C6 alkoxy, C3-C8 cycloalkyl, C3-C8 cycloalkoxy, aryl, C-C5 arylalkyl, C-C6-arylalkoxy, cycloalkyl C3-C8) - C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl-C 1 -C 6 alkoxy, C 3 -C 8 cycloalkoxy C 1 -C 6 alkyl and C 3 -C 8 cycloalkoxy -alcoxy of CrC6, wherein the cyclic portion of the last nine radicals mentioned in each case is unsubstituted or substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X1 , where -B- and X1 are as defined below, and wherein the non-cyclic portion of the last thirteen mentioned radicals of the group G4, in each case is unsubstituted or substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X2, where X2 is as Huaááitt ig &üi i defined below, and wherein the non-cyclic portion of the radicals of the group G 4 may in each case be interrupted by one or two heteroatoms identical or different from the group consisting of oxygen and sulfur, or two R 1 of two groups (CR1R2) directly adjacent, together with the bond between the carbon atoms of the groups, form a double bond, or two R3 of two groups (CR3R4) directly adjacent, together with the bond between the carbon atoms of the groups, form a double bond, or two R3 and two R4 of two groups (CR3R4) directly adjacent, together with the bond between the carbon atoms of the groups, form a triple bond, or R3 is a point of attachment for the double bond in the case where Y is a trivalent unit = N-0- adjacent to a group CR3R4, and / or -B- is a direct link or a divalent unit of the group consisting of -O-, -S- , -NR11-, -CO-, -C02-, -0C02-, -SO-, -S02-, -S020- and -S02NR14- and / or; X1 is hydrogen, Ci-Cß alkyl, C2-C6 alkenyl, C2-C8 alkynyl, C3-C6 cycloalkyl or heterocyclyl having from 3 to 6 ring atoms, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen and sulfur, and wherein the last five mentioned radicals are unsubstituted or substituted with one or more identical or different halogen atoms, and / or X2 is hydrogen or heterocyclyl having from 3 to 9 atoms of ring, 1, 2 or 3 of which originate from the group consisting of nitrogen, a ri ^^^^ iütaüaii oxygen and sulfur, which is not substituted or is substituted with 1, 2 or 3 identical or different halogen atoms, and / or R5, R6 each independently of one another, is a radical of the group G4 , and / or R7 is hydrogen, amino, alkylcarbonyl, alkylamino or dialkylamino, which in each case has from one to four carbon atoms in the alkyl radical, is an acyclic or cyclic hydrocarbon radical having in each case from one to six carbon atoms, or is heterocyclyl having three to six ring atoms and one to three ring heteroatoms of the group consisting of nitrogen, oxygen and sulfur; wherein each of the last six mentioned radicals is unsubstituted or substituted with one or more radicals identical or different from the group consisting of halogen, C? -C4 alkoxy, CrC haloalkoxy, C1-C4 alkylthio, C2-C4 alkenyl, C2-C4 alkynyl, C2-C alkenyloxy, C2-C4 alkynyloxy, hydroxyl, amino, alkylamino, -dialkylamino, nitro, carboxyl, cyano, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, formyl, carbamoyl, mono- and dialkyl (C 1 -C 4) aminocarbonyl, C 1 -C 4 alkylsulfonyl, haloalkylsulfonyl of C 1 -C 4 and, in the case of cyclic radicals, also C 1 -C 4 alkyl and halo C 1 -C 4 alkyl, and / or R 8 is C 6 -C 6 alkyl, which is unsubstituted or substituted with one or more radicals identical or different from the group consisting of halogen, cyano, nitro, thiocyanate, hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenyl, alkynyl of C2-C4, phenyl, C3-Cg cycloalkyl, C3-Cg cycloalkoxy and heterocyclyl having ?. ^^?. ^ A? ^^ S. ^^ A MaH > Mfe? ^ wU ^ i of three to six ring atoms and one to three ring heteroatoms of the group consisting of oxygen, nitrogen and sulfur, which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, amino, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halo C 1 -C 4 alkyl and halo C 1 -C 4 alkoxy; is C3-C8 cycloalkyl or C3-C8 cycloalkoxy, wherein the last two mentioned radicals are unsubstituted or are substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano, C1-C4 alkyl , C 1 -C 4 alkoxy, haloCi C 4 alkyl and CC haloalkoxy, and / or R 9, R 10 each independently of one another, is hydrogen, amino, Ci-Cß alkylcarbonyl. Ci-Cβ alkylamino, Ci-Cβ dialkylamino, Ci-Cβ alkyl, C3-C8 cycloalkyl, C-Cß alkoxy, C3-C8 cycloalkoxy or heterocyclyl having from 3 to 6 ring atoms and from 1 to 3 ring heteroatoms of the group consisting of oxygen, nitrogen and sulfur, wherein each of the last eight radicals mentioned is unsubstituted or substituted with one or more radicals identical or different from the group consisting of halogen, amino, hydroxyl and, in the case of cyclic radicals, also C1-C4 alkyl, C1-C4 alkoxy, halo-C1-C4 alkyl and halo-C1-C4 alkoxy, and / or R11 is hydrogen, amino, C- alkylamino. -C6, dialkylamino of C -? - C6, alkyl of CrC6, cycloalkyl of C3-C8, cycloalkyl (C3-C8) -alkyl of C -? - C6, alkoxy of CI-CT, alkoxy (C -? - C6) ) -alcox of Ci-Cß, C3-C8 cycloalkoxy, C-pCß alkylcarbonyl, where the last nine radicals mentioned . . . . ... .. - .- ^ .... 1. ^ ..... ....... . . to... ... . .. ..... i. 1 _____________________ are not substituted or are substituted with one or more radicals identical or different from the group consisting of halogen, amino, hydroxyl and, in the case of cyclic radicals, also C 1 -C 4 alkyl, C 4 alkoxy, haloalkyl of C 1 -C 4 and halo C 4 alkoxy, and / or R 12, R 13 each, independently of one another, is hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl, C1-C6 phenylalkyl, C3-C8 cycloalkyl, (C3-C8) cycloalkyl-C6 alkyl, wherein the cyclic portion of the last four mentioned radicals, in each case, is unsubstituted or is substituted with one or more identical or different radicals from the group consisting of C 1 -C 4 alkyl, halo C 1 -C 4 alkyl, C 1 -C 4 alkoxy and halo C 1 -C 4 alkoxy, or R 12 and R 3 together with the N-CO group -N that carries them, they form a ring of 5 to 8 members that, in addition to the two nitrogen atoms mentioned above, can contain a hetero additional volume of the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, C-C4 alkyl and haloalkyl CC; R 4 is hydrogen or C 1 -C 7 alkyl or C 3 -C 8 cycloalkyl, each of which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, phenyl, hydroxyl, alkoxy C -.- C4, and haloalkoxy of C -.- C4, and / or R15 and R16 each, independently of one another, is hydrogen, phenyl, Ci-Cß alkoxy. phenylalkyl of C-i-Cß, C6-alkyl, M m? Im? I ^? R ^ U ^ k ^ A '- • * "" - • • "" "- ^ - • * a & ^^ d, .ÁMliH ihé alquiltio de Ci-Ce, en where the last five mentioned radicals are unsubstituted or substituted, and wherein the aliphatic carbon skeleton of the last three mentioned radicals can be interrupted with one or more heteroatoms identical or different from the group consisting of oxygen and sulfur. Preference is given to the compounds of formula I and salts thereof, in which R1 and R2 of a group (CR1R2), together with the carbon atom carrying them, form a carbonyl group, a CR15R16 group or a ring of 3 to 6 members which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X1, or two R1 of two groups (CR1R2) directly adjacent or not directly adjacent, together with the carbon atoms carrying or linking them, form an unsubstituted or substituted 3 to 6 membered ring which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X1. Also, preference is given to the compounds of formula I wherein R3 and R4, together with the carbon atom carrying them, form a carbonyl group, a CR15R16 group or a 3-6 membered ring which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X1, or two R3 of two groups (CR3R4) directly adjacent or not directly adjacent, together with the carbon atoms carrying or linking them, form an unsubstituted or substituted 3 to 6-membered ring which may contain one or two heteroatoms identical or different from the group it consists of oxygen, nitrogen and sulfur, which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X1. In addition, preference is given to the compounds of formula I and the salts thereof wherein R3 and R5 of two groups (CR3R4) - or (CR5R6) - directly adjacent or not directly adjacent, together with the carbon atoms linking them , form a 3 to 6 membered unsubstituted or substituted ring which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more identical or different radicals of the group consisting of halogen, nitro, cyano and -B-X1, or R5 and R6 together with the carbon atom that bears them, form a carbonyl group, a CR15R16 group or a 3 to 6 member ring which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -BX1, or R6 is hete rociclilo. Likewise, preference is given to compounds of formula I and salts thereof where R9 and R10 together with the nitrogen atom carrying them form a heterocycle having a total of three to six ring atoms and of these, one to four ring heteroatoms, wherein the other ring heteroatoms which may be present in addition to the nitrogen atom, are selected from the group consisting of oxygen, nitrogen and sulfur, and wherein this heterocycle is unsubstituted or substituted with up to three identical or different radicals, preferably from the group which consists of halogen, amino, hydroxyl, C1-C4 alkyl, C1-C4 alkoxy, halo-C-C alkyl, and C4 haloalkoxy. further, preference is given to the compounds of formula I and the salts thereof wherein R15 and R16 together with the carbon atom carrying them, form a 3-6 membered ring which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, C1-C4 alkyl and halo-C4-C4 alkyl.

Particular preference is given to the compounds of formula I and the salts thereof wherein aryl is a mono- or bicyclic aromatic radical having 5 to 10 ring atoms, 1, 2, 3 or 4 of which may, in each case, independently of one another, originate from the group consisting of oxygen, sulfur and nitrogen, which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, hydroxyl, amino, formyl, C1-6 alkoxycarbonyl. C4, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkoxycarbonyl, C 1 -C 4 haloalkylcarbonyl, C 1 -C 4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C-1-C4 alkoxy, (C? -C4) alkoxy-C1-C4alkyl, haloalkoxy (C-? - C4) -alkyl C1-C4, haloalkoxy (C? -C4) - [halo-C1-C4 alkyl], alkoxy (CrC4) - [halo-C1-C4 alkyl], cycloalkyl of C3-C6, cycloalkyl (C3-C6) ) -C1-C4 alkyl, (C3-C6) cycloalkyl- [halo-C1-C4 alkyl], (C3-C6) halo-cycloalkyl- [halo] C1-C4 alkyl, halo-cycloalkyl l (C3-C6) -alkyl C1-C4, C-pCβ alkylamino, Ci-Cβ dialkylamino, C? -C6 alkylaminocarbonyl, aminosulfonyl, alkyl (CrC6) aminosulfonyl, dialkyl (C -? - C6) aminosulfonyl, halo-C1-C4 alkyl and halo C4-alkoxy, -Y- is a divalent unit of the group consisting of -O-, -S-, -NR11-, -C02-, -SO-, -S02-. -S020-, and -S02NR14-, or a unit of the group consisting of -NH-CO-NH- and -OCONH-, or a unit of the group consisting of -O-NH-, -0-N = and -OCH2CH2-0-, R, R2 are in each case, independently of one another, a radical of a group G5 comprising hydrogen, C-C6 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci-Cβ alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, Ci-C6 arylalkyl and (C3-C6) cycloalkyl-C-Cß alkyl, wherein the cyclic portion of the last four mentioned radicals, in each case, is not substituted or is substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X1, where -B- and X1 are as defined below, and wherein the non-cyclic portion of the last eight mentioned radicals of the group G5, in each case, is unsubstituted or is substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X2, wherein X2 is as defined below, and wherein the non-cyclic portion of the radicals of group G5, in each case may be interrupted by one or more heteroatoms identical or different from the group consists of oxygen and sulfur, or two R's of two groups (CR1R2) directly to adjacent, together with the bond between the carbon atoms of the groups, form a double bond, or two R1 and two R2 of two groups (CR1R2) directly adjacent, together with the bond between the carbon atoms of the groups, form a triple bond or R1 is a point of attachment for the double bond in the case where Y is a trivalent unit = N-0- adjacent to a group CR1R2, R3, R4 in each case, independently of each other, is a radical of a G6 group comprising hydrogen, Ci-Cß alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C -? -C6 alkoxy, C3-CS cycloalkyl, *. » *. .. k.? . i ..¡ .. .., .t. . . ... .. ... ...... ....., "..." ... j. . .. .. ....to. t * 1 C3-C8 cycloalkoxy, aryl, C1-C4 arylalkyl, C1-C4 arylalkoxy, (C3-C8) cycloalkyl-CrC4 alkyl, (C3-C8) cycloalkyl-C1-C4alkoxy, cycloalkoxy (C3-) C8) -C1-C4 alkyl and (C3-C8) cycloalkoxy-C1-C4alkoxy, wherein the cyclic portion of the last nine radicals mentioned in each case is unsubstituted or substituted with one or more identical radicals or different from the group consisting of halogen, nitro, cyano and -B-X1, wherein -B- and X1 are as defined below, and wherein the non-cyclic portion of the last thirteen mentioned radicals of the group G6, in each case is not substituted or is substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X2, wherein X2 is as defined below, and wherein the non-cyclic portion of the radicals of group G6 may in each case be interrupted by a heteroatom of the group consisting of oxygen and sulfur, or either two R3 of two groups (CR3R4) directly adjacent, together with the bond between the carbon atoms of the groups, form a double bond, or two R3 and two R4 of two groups (CR3R4) directly adjacent, together with the bond between the carbon atoms of the groups form a tiple bond, or R3 is a point of attachment for the double bond in the case where Y is a trivalent unit -0-N = adjacent to a group CR3R4, and -B - is a direct bond or a divalent unit of the group consisting of -O-, -S-, -NR11-, -CO-, -C02-, -SO-, -S02- and -S02NR14-, X1 is hydrogen, C-C4 alkyl, C2-C4 alkenyl, C2-C alkynyl, C3-C6 cycloalkyl or heterocyclyl having from 3 to 6 ring atoms, 1, 2 or 3 of which originate from the upo consisting of nitrogen, oxygen and sulfur, and wherein the last five mentioned radicals 5 are unsubstituted or substituted with up to five identical or different halogen atoms, X 2 is hydrogen or is heterocyclyl having 3 to 6 ring atoms , 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen and sulfur, which is unsubstituted or substituted by 1, 2 or 10 3 identical or different halogen atoms, R5, R6 each, independently one of another, is a radical of the group G6, R7 is hydrogen, amino, alkylcarbonyl, alkylamino or dialkylamino, which in each case has from one to four carbon atoms in the alkyl radical, or is an acyclic or cyclic hydrocarbon radical that has in each case from one to six carbon atoms, wherein each of the last five radicals mentioned is unsubstituted or is substituted with one or more radicals identical or different from the group consists of halogen, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, hydroxyl, amino, alkylamino of dd, dialkylamino of d-C4, nitro, carboxyl, cyano, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, formyl, carbamoyl, > iiiriiii-ti-á¡Bí-te-t-ri¡a-iídá-d ^ tiaMMiiia alkylsulfonyl of CrC4, halo-alkylsulfonyl of C 1 -C 4 and, in the case of cyclic radicals, also C 1 -C 4 alkyl and halo- C 1 -C 4 alkyl, R 8 is d-Cβ alkyl, which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, cyano, hydroxyl, C 1 -C 4 alkoxy, dith alkylthio, dd alkylsulfonyl, C2-d alkenyl, C2-d alkynyl, phenyl, C3-Cg cycloalkyl, C3-Cg cycloalkoxy, is C3-C8 cycloalkyl or C3-C8 cycloalkoxy, wherein the last two mentioned radicals they are unsubstituted or substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano, C1-C4 alkyl, d-C4 alkoxy, haloCiC4 alkyl and dd haloalkoxy, R9 , R10 each independently of one another, is hydrogen, amino, C1-C4 alkylcarbonyl, C1-C4 alkylamino, dialkylamino dd, alkyl dd, cyclo C3-C8 alkyl, C1-C4 alkoxy, C3-C8 cycloalkoxy or heterocyclyl having from 3 to 6 ring atoms and from 1 to 3 ring heteroatoms of the group consisting of oxygen, nitrogen and sulfur, wherein each one of the last eight mentioned radicals is unsubstituted or substituted with up to four identical or different radicals from the group consisting of halogen, amino, hydroxyl and, in the case of cyclic radicals, also C1-C4 alkyl, C1-6 alkoxy C4, halo-C1-C4 alkyl and halo-C1-C4 alkoxy, R11 is hydrogen, amino, C1-C4 alkylamino, dialkylamino of d-C4, alkyl of dd, cycloalkyl of C3-C8, cycloalkyl (C3- C8) -alkyl of d-C4, alkoxy of C1-C4, alkoxy (CrC4) -alkoxy of C1-C4, cycloalkoxy of C3-C8, alkylcarbonyl of CrC4, wherein the last nine radicals mentioned are unsubstituted or substituted with one or more identical or different halogen atoms, and in the case of cyclic radicals, also dd alkyl, alkoxy d e C1-C4, haloalkyl of dd and haloalkoxy of C1-C4, R14 is hydrogen or alkyl of dC or cycloalkyl of C3-C6, each of which is unsubstituted or substituted by one or more identical radicals or different from the group consisting of halogen, dd alkoxy and halo-C 1 -C 4 alkoxy, and / or R 15, R 16 each independently of one another, is hydrogen, phenyl, dd alkoxy, phenyl-C 1 -C 4 alkyl, of d-C4, C1-C4 alkylthio, wherein the last five mentioned radicals are unsubstituted or substituted with one or more identical or different halogen atoms and, in the case of cyclic radicals, also one or more identical or identical radicals different from the group consisting of halogen, C1-C4 alkyl and halo-C1-C4 alkyl. Preference is also given to the compounds of formula I according to the invention, which only contain one or more of the above-mentioned preferred radicals. Particular preference is also given to compounds of formula I wherein R1 and R2 of a group (CR1R2), together with the carbon atom carrying them, form a carbonyl group, a CR15R16 group or a 3-6 membered ring which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen, nitro, cyano and -B-X1 , or 5 two R1 of two groups (CR1R2) directly adjacent or not directly adjacent, together with the carbon atoms that carry or link them, form an unsubstituted or substituted 3 to 6 membered ring which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted with up to four identical or different radicals from the group consisting of halogen, nitro, cyano and -B- X1 Likewise, particular preference is given to the compounds of formula I wherein R3 and R4 together with the carbon atom carrying them, form A carbonyl group, a CR15R16 group or a 3-6 membered ring, which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by up to four radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X1, or 20 two R3 of two groups (CR3R4) directly adjacent or not directly adjacent, together with the carbon atoms that carry or link them, form an unsubstituted or substituted 3 to 6 membered ring which may contain one or two heteroatoms identical or different from the group it consists of oxygen, nitrogen and sulfur, and is unsubstituted or substituted with up to four identical or different radicals from the group consisting of halogen, nitro, cyano and -B-X1. In addition, particular preference is given to compounds of formula I wherein R3 and R5 of two groups (CR3R4) - or (CR5R6) - directly adjacent or not directly adjacent, together with the carbon atoms that link them, form a ring of 3 to 6 members unsubstituted or substituted which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen , nitro, cyano and -B-X1, or R5 and R6 together with the carbon atom that bears them, form a carbonyl group, a CR15R16 group or a 3 to 6 member ring which may contain one or two identical or different heteroatoms of the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X1, or R6 is heter occylil Particular preference is also given to the compounds of formula I wherein R9 and R10 together with the nitrogen atom carrying them form a heterocycle having a total of three to six ring atoms and of these, from one to four heteroatoms of ring, wherein the other heteroatoms that may be present, in addition to the nitrogen atom that is present, are selected from the group consisting of oxygen, nitrogen and sulfur, and wherein this heterocycle is unsubstituted or substituted. Also, particular preference is given to the compounds of formula I wherein R15 and R16 together with the carbon atom carrying them form a 3-6 membered ring which may contain one or two heteroatoms which are identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen, dd alkyl and halo-C1-C4 alkyl. Particular preference is given to compounds of formula I wherein aryl is phenyl, naphthyl, pyridinyl, pyrimidinyl, furanyl, benzofuranyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, oxadiazolyl, or thienyl, each of which is unsubstituted or is substituted with one or more radicals identical or different from the group consisting of halogen, hydroxyl, 20 amino, formyl, C1-C4 alkoxycarbonyl, d-C4 alkylcarbonyl, dd alkyl, C2-C4 alkenyl, C2- alkynyl C, C 1 -C 4 alkoxy, C 1 -C 4 alkylamino, C 1 -C 4 dialkylamino, aminocarbonyl, C 1 -C 4 alkylaminocarbonyl, CC dialkylaminocarbonyl, aminosulfonyl, alkylaminosulfonyl of CrC 4, t ^ mt dialkylaminosulfonyl of dd, haloalkyl of d-C4, haloalkoxy of C1-C4, halo-alkylthio of CrC2, alkylsulfinyl of C? -C2, alkylsulfonyl of C C2, haloalkylthio of C? -C2, halo- C 1 -C 2 alkylsulfinyl and C 1 -C 2 haloalkylsulfonyl; -Y- is a divalent unit of the group consisting of -O-, -S-, -NR11-, -C02-, -SO- and -S02-, or a divalent unit of the group consisting of -NH-CO -NH- and -O-CO-NH-, or a unit of the group consisting of -O-NH-, -0-N = and -OCH2CH20-, m is an integer from 0 to 5, preferably 0.1 , 2 or 3, in particular 0 or 1; n is an integer from 1 to 5, preferably 1, 2, 3 or 4, in particular 1, 2 or 3; R1, R2 each independently of one another is a radical of a G7 group comprising C?-C4 alkyl, C2-C4 alkenyl, C2-d alkynyl, C1-C4 alkoxy, hydrogen, cycloalkyl of d- Cß, wherein the last mentioned radical is unsubstituted or is substituted with up to four identical or different radicals from the group consisting of halogen and -B-X1, and wherein the first four mentioned radicals of the group G7, are not substituted or are substituted with one or more radicals identical or different from the group consisting of halogen and -B-X2, wherein X2 is as defined below, or R1 and R2 together with the carbon atom carrying them form a carbonyl group , O well ^^^ m ^^^^^^^^^ R1 is a junction point for the double bond in the case where Y is a trivalent unit = N-0- that is adjacent to a group CR1R2, and R3, R4 each, independently of one another, is a radical of a group G8 comprising hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C2-d alkynyl, Ci-Cß alkoxy, C3-Cβ cycloalkyl, C3-C6 cycloalkoxy, aryl, arylalkyl of d-C2, arylalkoxy of C? -C2, cycloalkyl (C3-C6) -alkyl of C C2 and cycloalkoxy (C3-C8) -alkyl of C C4, wherein the cyclic portion of the last seven mentioned radicals, in each case, is not replaced or is substituted with up to four identical or different radicals from the group consisting of halogen, nitro, cyano and -B-X1, wherein -B- and X1 are as defined below, and wherein the non-cyclical portion of the last eleven mentioned radicals of group G8, in each case, is unsubstituted or is substituted with one or more identical or different radicals from the group consisting of halogen, nitro, cyano and -B-X2, wherein X2 is as defined below, or R3 and R4 together with the carbon atom carrying them forms a carbonyl group, or R3 is a point of union for the double bond in the case where Y is a trivalent unit -0-N = that is adjacent to a group CR3R4, -B- is a direct bond or a divalent unit of the group consisting of -O-, - S-, -NR11-, -CO- and -C02-; X1 is hydrogen, C? -C4 alkyl, C2-d alkenyl, C2-C alkynyl or C3-C6 cycloalkyl, the last four mentioned radicals are unsubstituted or substituted with up to five identical or different halogen atoms, X2 is hydrogen or heterocyclyl having 3 to 6 ring atoms, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen or sulfur, which is unsubstituted or substituted with one or more halogen atoms identical or different, R5 is hydrogen, dd alkyl, d-C4 haloalkyl or d-Cβ cycloalkyl, R6 is hydrogen, dd alkyl, C2-C4 alkenyl, C2-C4 alkynyl, dd alkoxy, C3-C6 cycloalkyl, (C3-C6) cycloalkyl-C1-C4 alkyl, (C3-C6) cycloalkoxy-C1-C4 alkyl, C3-C6 cycloalkoxy, (C? -d) alkoxy-C alkyl? -C or halo-C1-C4 alkyl, R7 is hydrogen, amino or C1-C4 alkyl, R8 is C1-C4 alkyl, halo-C1-C4 alkyl, C3-C6 cycloalkyl, halo-C3 cycloalkyl -C6 or (C3-C6) cycloalkyl-C1-C4alkyl, R9, R10 independently of one another, is hydrogen, amino, formyl or C1-C4alkyl, or R11 is hydrogen, amino, C1-C4alkylamino, dialkylamino of d-C4, dC alkyl or C3-C6 cycloalkyl, wherein the last five mentioned radicals are unsubstituted or substituted with one or more identical or different halogen atoms, and / or R14 is hydrogen or C1 alkyl -C4. Particular preference is also given to the compounds of formula I according to the invention, which contain only one or more of the preferred radicals mentioned above. Also very particular preference is given to compounds of formula I in which two groups (CR1R2) directly adjacent or not directly adjacent, together with the carbon atoms that carry or link them, form a ring of 3, 5 or 6 members which may contain up to 2 heteroatoms of the group consisting of oxygen, sulfur and nitrogen, and which is unsubstituted or substituted with up to four identical or different radicals from the group consisting of halogen and -B-X1. Also very special preference is given to the compounds of formula I wherein two R3 of two groups (CR3R4) directly adjacent or not directly adjacent, together with the carbon atoms that carry or link them, form a 3, 5 or 6 member ring that can contain up to two heteroatoms from the group consisting of oxygen, sulfur and nitrogen, and which is not substituted or is substituted with up to four identical or different radicals from the group consisting of halogen and -B-X1. Likewise, very special preference is given to the compounds of formula I wherein R3 and R5 of two groups (CR3R4) - or (CR5R6) directly adjacent or not directly adjacent, together with the carbon atoms ^^^ ¿Sm? Ti M that bind them, form a ring of 3, 5 or 6 members that can contain up to two heteroatoms of the group consisting of oxygen, sulfur and nitrogen, and that is not substituted or is substituted with four identical or different radicals from the group consisting of halogen and -B-X1. In addition, very particular preference is given to the compounds of formula I wherein R9 and R10 together with the carbon atom carrying them, form a heterocycle having from three to six ring atoms and one to two ring heteroatoms, wherein the other ring heteroatoms which may be present in addition to the nitrogen atom that is present, are selected from the group consisting of oxygen and nitrogen. The present invention also provides processes for preparing the compounds of formula I or salts thereof, comprising: (a) reacting a compound of formula (II) R8-Fu (II) in which Fu is a functional group of the group which consists of carboxylic ester, carboxylic orthoester, carbonyl chloride, carboxamide, carboxylic anhydride and trichloromethyl, with a biguanide of formula (III) or an acid addition salt thereof, NH NH Aryl (CR1R2) m - Y - (CR3R ") n - r CoR5J - N NRR7 '- - U" _- N MR9R10 (MI) H (b) reacting a compound of formula (IV) wherein Z1 is an interchangeable radical or a leaving group, for example, chloro, trichloromethyl, alkylsulfonyl of dC or phenyl-alkyl (C? -d) sulfonyl or alkyl (CrC4) -phenylsulfonyl, unsubstituted or substituted, with an amine of formula (V) or an acid addition salt thereof, R6 Aryl (C R1 R2) - Y - (C R3R4) n C R5 N H R7 (v) in the formulas (II), (III), (IV) and (V), the radicals R1 to R10, Y and n and m, are as defined for the formula (I). Preferably, the compounds of the formulas (II) and (III) are placed in a base-catalyzed reaction in an inert organic solvent such as, for example, tetrahydrofuran (THF), dioxane, acetonitrile, dimethylformamide. . . • i. . . • i. .-, i ... .. ^ A. ^^ a-i ^ lJfcailJi ^ (DMF), methanol and ethanol, at temperatures between -10 ° C and the boiling point of the solvent, preferably between 20 ° C and 60 ° C. If the acid addition salts of formula (III) are used, they are released in situ with the aid of a base. Suitable basic bases or catalysts are the alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alkoxides, alkaline earth metal hydroxides, alkaline earth metal hydrides, alkaline earth metal carbonates, or organic bases such as triethylamine or 1,8-diazabicyclo [5.4.0] -7-undequene (DBU). The base in question is used, for example, in the scale of 0.1 to 3 molar equivalents, based on the compound of formula (III). The compound of formula (II) can be used, in relation to the compound of formula (III), for example, in equimolar amounts or in an excess of up to 2 molar equivalents. In principle, the corresponding procedures are known from the literature (compare: "Comprehensive Heterocyclic Chemistry" - Comprehensive heterocyclic chemistry - by AR Katritzky, CW Rees, Pergamon Press, Oxford, New York, 1984, vol.3, part 2B, ISBN 0 -08-030703-5, page 290). Preferably, the compounds of formulas (IV) and (V) are placed in a base-catalyzed reaction in an inert organic solvent such as, for example, THF, dioxane, acetonitrile, DMF, methanol and ethanol, at temperatures between -10 ° C and the boiling point of the solvent or mixture of solvents in question, preferably from 20 ° C to 60 ° C; if the compound (V) is used as an acid addition salt, it is released in situ with a base, if appropriate. Suitable basic bases or catalysts are the alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alkoxides, alkaline earth metal hydroxides, alkaline earth metal hydrides, alkaline earth metal carbonates, or organic bases such as triethylamine or 1, 8-diazabicyclo [5.4.0] -7-undequene (DBU). The base 5 in question is usually used in the scale of 1 to 3 molar equivalents, based on the compound of formula (IV), and the compound of formula (IV) can be used, for example, in equimolar amounts based on the compound of formula (V), or in an excess of up to 2 molar equivalents. In principle, the corresponding procedures are known from the literature (see: "Comprehensive Heterocyclic Chemistry" by A. R. Katritzky, C.W. Rees, Pergamon Press, Oxford, New York, 1984, vol.3, part 2B; page 482). The starting materials of formulas (II), (III), (IV) and (V) are commercially available, or can also be prepared by of the known methods of the literature or analogously to them. The compounds can also be prepared, for example, by one of the methods described below. The compound of formula (IV), or a direct precursor thereof, can be prepared, for example, in the following manner: 1. Reaction of a compound of formula (II) with an amidinothiourea derivative of formula (VI), NH NH Z2-S-NR7- ILN_U_NRßR? ° (VI) H wherein Z2 is d-d alkyl or phenylalkyl of d-d, and R9 and R10 are as defined for formula (I), which gives compounds of formula (IV) wherein Z1 = -SZ2. 2. Reaction of an amidine of formula (VII) or an acid addition salt thereof, wherein R8 is as defined for formula (I), with a N-cyano-dithioiminocarbonate of formula (VIII), 15 S-zJ NC- N = H (VIII) S-Z3 wherein Z3 is d-d alkyl or phenylalkyl of d-d, which gives compounds of formula (IV) wherein Z1 = -S-Z3. 3. Reaction of an alkali metal dicyanamide with a carboxylic acid derivative of the aforementioned formula (II), which gives compounds of formula (IV) wherein Z 1 = NH 2. 4. Reaction of trichloroacetonitrile with a nitrile of formula (IX), * - - »- > »- '-'» »" * • - -. • »'........ -. - *. -,..«, * ",», R8 - CN (IX) in which R8 is like is defined for formula (I), which initially gives compounds of formula (X), wherein Z1 and Z4 are each CCI3, which by subsequent reaction with compounds of formula HNR9R10 (R9 and R10 are as defined for formula (I)), gives compounds of formula (IV) wherein Z1 = CCI3. The reaction of the carboxylic acid derivatives of formula (II) with the amidinothiourea derivatives of formula (VI) is preferably carried out by base catalysis in an organic solvent such as, for example, acetone, THF, dioxane, acetonitrile, methanol, ethanol, at temperatures from -10 ° C to the boiling point of the solvent, preferably from 0 ° C to 20 ° C. However, the reaction can also be carried out in water or in aqueous mixtures of solvents comprising one or more of the organic solvents mentioned above. If (VI) is used as acid addition salt, it can be released in situ using a base, if appropriate. Suitable basic bases or catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alkoxides, alkaline earth metal hydroxides, alkaline earth metal hydrides, alkaline earth metal carbonates, or organic bases such as triethylamine.

At ^ Hl ^^ tftaaM ^ M ^ M ¿¿iá ^ íÍ or 1, 8-diazabicyclo [5.4.0] -7-undequeno (DBU). The base in question is used for example in the scale of 1 to 3 molar equivalents, based on the compound of formula (VI). The compounds of the formulas (II) and (VI) can be used, for example, in equimolar amounts or with an excess of up to 2 molar equivalents of the compound of the formula (II). In principle, the corresponding procedures are known from the literature (see: H. Eilingsfeld H., Scheuermann, Chem. Ber., 1967, 100, 1874), the corresponding intermediates of formula (IV) are novel. The reaction of the amidines of formula (VII) with the N-cyano-dithioiminocarbonates of formula (VIII) is preferably carried out by base catalysis in an inert organic solvent such as, for example, acetonitrile, DMF, dimethylacetamide (DMA), N- methylpyrrolidone (NMP), methanol and ethanol, at temperatures from -10 ° C to the boiling point of the solvent, preferably from 20 ° C to 80 ° C. If (VII) is used as acid addition salt, it can be released in situ using a base, if appropriate. Suitable basic bases or catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alkoxides, alkaline earth metal hydroxides, alkaline earth metal hydrides, alkaline earth metal carbonates, or organic bases such as triethylamine or , 8-diazabicyclo [5.4.0] -7-undequene (DBU). The base in question is used for example in the scale of 1 to 3 molar equivalents, based on the compound of formula (VIII); The compounds of formulas (VII) and (VIII) can usually be used in equimolar amounts or in an excess of up to 2 molar equivalents of the compound of formula (II). In principle, the corresponding procedures are known from the literature (see: TA Riley, WJ Henney, NK Dalley, BE Wilson, RK Robins, J. Heterocyclic Chem., 1986 23 (6), 1706-1714), the corresponding intermediates of formula (IV) are novel. Intermediates of formula (X) wherein Z 1 = chloro can be prepared by reacting alkali metal dicyanamide with a carboxylic acid derivative of formula (II), in which case Fu is preferably the carbonyl chloride or carboxamide functional group. The reaction components are, for example, reaction with acid catalysis in an inert organic solvent such as for example toluene, chlorobenzene, chlorinated hydrocarbons, at temperatures between -10 ° C and the boiling point of the solvent, preferably from 20 ° C to 80 ° C, and the resulting intermediates can be chlorinated in situ using an appropriate chlorination reagent, for example phosphorus oxychloride. Suitable acids are for example halohydric acids such as HCl, or Lewis acids such as AICI3 or BF3 (see US 5,095,113). The intermediates of formula (X) wherein Z 1, Z 4 = trihalomethyl can be prepared by reacting the corresponding trihaloacetonitriles with a carbonitrile of formula (IX). The reaction components are, for example, reaction with acid catalysts in an inert organic solvent such as toluene, chlorobenzene or chlorinated hydrocarbons at temperatures between -40 ° C and the boiling point of the solvent, preferably from -10 ° C to 30 ° C. ° C. Examples of suitable acids are halohydric acids such as HCl, or Lewis acids such as AICI3 or BF3 (see EP-A-130 939). The intermediates of formula (IV) wherein Z 1 = alkyl (d-5 d) mercapto or unsubstituted phenyl-alkyldicarboxylate can be converted into an inert organic solvent such as toluene, chlorobenzene, chlorinated hydrocarbons or others, temperatures between -40 ° C and the boiling point of the solvent, preferably from 20 ° C to 80 ° C, using an appropriate chlorination reagent such as elemental chlorine or phosphorus oxychloride, in chlorotriazines more Reagents of formula (IV) in which Z1 is Cl (see J.K. Chakrabarti, D.E. Tupper, Tetrahedron 1975, 31 (16), 1879-1882). The intermediates of formula (IV) in which Z 1 = unsubstituted or substituted alkyl (dC 4) mercapto or phenyl-alkyl (C-C 4) mercapto or alkyl (C 1 -C 4) -phenylthio can be oxidized in a appropriate solvent, for example Chlorinated hydrocarbons, acetic acid, water, alcohols, acetone, or mixtures thereof, at temperatures between 0 ° C and the boiling point of the solvent, preferably from 20 ° C to 80 ° C, using an appropriate oxidation reagent such such as m-chloroperbenzoic acid, hydrogen peroxide, potassium peroxymonosulfate (see TA Riley, WJ Henney, NK Dalley, B.E. Wilson, R.K. Robins, J. Heterocyclic Chem., 1986, 23 (6), 1706-1714). For the preparation of the acid addition salts of the compounds of formula (I), suitable acids are the following: halohydric acids such as hydrochloric acid or hydrobromic acid, and also phosphoric acid, nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids such as acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid or lactic acid, and also acids sulfonic acids such as p-toluenesulfonic acid or 1,5-naphthalene disulfonic acid. The acid addition compounds of formula (I) can be obtained in a simple manner by customary methods of salt formation, for example by dissolving a compound of formula (I) in an appropriate organic solvent such as for example methanol, acetone, Methylene chloride or benzine, and adding the acid at temperatures of 0 to 100 ° C, and can be isolated by means of the known forms, for example, by filtration, and if desired, can be purified by washing with an inert organic solvent . The base addition salts of the compounds of formula (I) are preferably prepared in inert polar solvents such as for example water, methanol or acetone, at temperatures of 0 to 100 ° C. Examples of suitable bases for preparing the salts according to the invention are alkali metal carbonates, such as potassium carbonate, alkali metal hydroxides and alkaline earth metal hydroxides, for example NaOH or KOH, alkali metal hydrides and hydride hydrides. alkaline earth metal, for example NaH, alkali metal alkoxides and alkaline earth metal alkoxides, for example sodium methoxide and potassium tert-butoxide, or ammonia or ethanolamine. With the "inert solvents" mentioned in the variants of the above processes, solvents are meant which are inert in each case under the respective reaction conditions, but not necessarily inert under all reaction conditions. The novel compounds of formula I have an outstanding herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous weeds. The active compounds also effectively act against difficult-to-control perennial weeds that produce stems of rhizomes, underground stems or other perennial organs. In this context, it does not matter if the substances are applied before sowing, preemergence or postemergence. Individually, examples of some representatives of the monocotyledonous and dicotyledonous weed flora that can be controlled with the compounds according to the invention can be mentioned, without said mention being intended to restrict the invention to specific species. Examples of monocotyledonous weed species against which the active compounds can act effectively are the species of Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and Cyperus of the annual group, and examples of perennial species are Agropyron, Cynodon , Imperata and Sorghum and also perennial species of Cyperus. In the case of dicotyledonous weed species, the spectrum of action extends to such species as, for example, Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon and Aids among the annuals, and Convolvulus, Cirsium, Rumex and Artemis among the perennial weeds. The novel active compounds also exhibit outstanding weed control that ^^^^ jj ^^^^ g ^^ h ^ riiM occur under specific growth conditions in rice, the examples being Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus. When the novel compounds are applied to the soil surface before germination, the emergence of the weed seedlings is completely prevented, or the weed grows until reaching the cotyledon stage but then its growth stops and finally they die completely afterwards. three to four weeks have passed. When the active compounds are applied postemergence to the green parts of the plants, there is also a very rapid and drastic termination of the growth after the treatment, and the weed plants remain in the growth stage in which they were at the time of the treatment. the application, or die completely after a certain time, so that in this way, the competition of the weeds that harms the plants of the crop, be eliminated very early and in a sustained manner. Although novel compounds have excellent herbicidal activity with respect to monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example wheat, barley, rye, rice, corn, sugar beet, cotton and soybeans, suffer only one damage minimum, or none. For these reasons, the present compounds are very suitable for the selective control of the growth of undesirable plants in crops of agriculturally useful plants or in ornamental plantations.

Due to their herbicidal and plant growth regulating properties, the active compounds can also be used to control harmful plants in crops of genetically engineered plants, known or yet to be developed. Generally transgenic plants have particularly advantageous properties, for example resistance to certain pesticides, in particular certain herbicides, resistance to plant diseases or organisms causing plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other particular properties relate for example to the amount, quality, stability in storage, composition and specific ingredients of the harvested product. In this manner, transgenic plants having an increased starch content or a modified quality of the starch, or having a different fatty acid composition of the harvested product are known. The use of compounds of formula I, or of their salts, according to the invention is preferred in economically important transgenic crops of utility and ornamental plants, for example of cereal such as wheat, barley, rye, oats, millet, rice. , manioc and corn, or in crops of sugar beet, cotton, soybean, rapeseed, potato, tomato, pea, and other vegetable species. Preferably, the compounds of formula I can be used as herbicides in crops of useful plants that are resistant or made resistant by genetic engineering, to the phytotoxic effects of the herbicides.

* R »i? I, - i ni t ?? n? in i? l i -HHÜ t go. t, ^^ fcJJMfc ^ a > ^ Mjl ^ MM ^, M ^ i¿M | ^ ilj fc ^ Mfcl ^ ^ M ^ M ^ MM ^^^^^^^^ l ^^ | M ^^^^^^^^^^^^ Conventional ways to prepare novel plants that have modified properties compared to known plants, include for example traditional culture methods and the generation of mutants. Alternatively, novel plants can be generated which have modified properties, with the aid of genetic engineering methods (see, for example, EP-A 0 221 044, EP-A 0 131 624). For example, several cases of changes have been described in genetically engineered crop plants for modifying the starch synthesized in plants (eg WO 10 92/1 1376, WO 92/14827, WO 91/19806), crop plants transgenic plants that are resistant to certain glufosinate-type herbicides (see, for example, EP-A 0 242 236, EP-A 0 242 246) or glyphosate type (WO 92/00377), or sulfonylurea type (EP-A 0 257 993, US 5013659), 15 - transgenic crop plants, for example cotton, which have the capacity to produce toxins of Bacillus thuringiensis (Bt toxins) which give the plants resistance against certain pests (EP-A 0 142 924, EP-A 0 193 259), transgenic crop plants having composition modified of 20 fatty acids (WO 91/13972). Many molecular biology techniques are known in principle that allow the preparation of novel transgenic plants that have modified properties; see for example, Sambrook et al., 1989, aaaLt_ »AliHUÍ» iM * _AD riMUfariMiiÉi ^^^^^ ¿JÜIiííMtt "Molecular Cloning, A Laboratory Manual" molecular -Cloning a laboratory- Manual, 2nd edition, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York; or Winnacker "Gene und Klone" -Genes and clones-, VCH Weinheim, 2nd edition, 1996, or Christou, Trends in Plant Science 1 (1996) 423-431. In order to carry out such genetic engineering manipulations, it is possible to introduce nucleic acid molecules into plasmids which allow the occurrence of a mutagenesis or a change in the sequence by recombination of DNA sequences. Using the standard procedures mentioned above, it is possible, for example, to exchange bases, remove partial sequences or add natural or synthetic sequences. To link DNA fragments with one another, it is possible to add adapters or linkers to the fragments. Can be prepared plant cells having reduced to a gene product, for example, by expressing at least one RNA of appropriate antisense RNA sense to achieve a cosuppression effect or by expressing at least activity, a ribozyme constructed appropriately, that specifically cut transcripts of the gene product mentioned above. For this purpose, it is possible to employ both DNA molecules which comprise the entire coding sequence of a gene product including any flanking sequence may be present as DNA molecules which comprise only parts of the coding sequence, it being necessary to be parts be large enough to cause an antisense effect on the cells. It is also possible to use DNA sequences which have a high degree of homology with the coding sequences of a gene product, even if they are not completely identical. When the nucleic acid molecules are expressed in plants, the synthesized protein can be located in any desired compartment of plant cells. However, to achieve localization in a certain compartment, it is possible, for example, to bind the coding region with DNA sequences that ensure localization in a certain compartment. Such sequences are known to the skilled artisan (see, for example, Braun et al, EMBO J. 11 (1992) 3219-3227; Wolter et al, Proc Natl Acad Sci USA 85 (1988),.... 846-850; Sonnewald et al., Plant J. 1 (1991) 95-196). The cells of transgenic plants can be regenerated in complete plants using known techniques. In principle, the transgenic plants can be plants of any desired plant species, particularly, monocotyledonous and dicotyledonous plants. In this way, it is possible to obtain transgenic plants that have modified properties, by means of overexpression, suppression or inhibition of genes or sequences of homologous genes (= natural) or by expression of genes or sequences of heterologous genes (= extraneous). The compounds according to the invention can preferably be used in transgenic crops that are resistant to herbicides U. '* * *. ~ L., Of the group consisting of the sulfonylureas, glufosinate-ammonium or glyphosate-isopropyl-ammonium and analogous active compounds. When the active compounds according to the invention are used in transgenic crops, in addition to the effects against the noxious plants that can be observed in other crops, there are frequently effects that are specific for application in the respective transgenic crop, for example a modified spectrum or specifically expanded weeds that can be controlled, modified application rates that can be used, preferably good combination capacity with the herbicides to which transgenic crops are resistant, and an effect on the growth and yield of crop plants transgenic Therefore, the invention also provides the use of the compounds according to the invention as herbicides to control harmful plants in plants of transgenic crops. further, the substances according to the invention exhibit outstanding properties of growth regulation in crop plants. They intervene with a regulating action in the endogenous metabolism of the plant, and therefore can be used for the controlled control of the content of the plant and to facilitate the harvest, for example, causing desiccation and slowing down of the growth. In addition, they are also suitable for controlling and inhibiting in general the unwanted vegetative growth without destroying the plants in doing so. In the case of many monocotyledonous and dicotyledonous crops, the inhibition of vegetative growth plays an important role, since it allows to reduce or completely prevent lodging. The invention also provides also herbicidal compositions and plant growth regulating compositions, which comprise the compounds of formula I. The novel compounds can be applied in the form of the usual formulations, known to those skilled in the art, such as wettable powders. , emulsifiable concentrates, sprayable solutions, powders or granules. The compounds of formula I can be formulated in various ways, depending on the prevailing biological and / or physicochemical parameters. Examples of suitable formulation options are: wettable powders (WP), water soluble powders (SP), water soluble concentrates, emulsifiable concentrates (EC), emulsions (EW) such as oil-in-water and water-in-oil emulsions, sprayable solutions , suspension concentrates (SC), oil or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusting powders (DP), seed coating compositions, granules for broadcast sowing and application to the soil granules (GR) in the form of microgranules, spray granules, coating granules and adsorption granules, water dispersible granules (WG), water soluble granules (SG), ULV formulations, microcapsules and waxes. These individual types of formulation are known in principle and are described, for example, in Winnacker-Küchler, "Chemische Technologie" -Technology chemistry-, volume 7, C. Hauser Verlag Munich, 4th edition, 1986; Wade van Valkenburg, "Pesticide Formulations" -Formulations of pesticides-, Marcel Dekker, New York, 1973; K. Martens, "Spray Drying Handbook" - Manual of spray-drying -, 3rd edition, 1979, G. Goodwin Ltd. London. Likewise, the necessary formulation aids, such as inert materials, surfactants and other additives, are known and are described, for example, in Watkins, "Handbook of Insecticide Dust Diluents and Carriers" - Diluents and insecticide dust vehicles manual - , 2nd edition, Darland Books, Caldweil New Jersey; H.v. Olphen "Introduction to Clay Colloid Chemistry" -Introduction to Colloidal Chemistry of Clays- 2nd edition, J. Wiley & Sons, New York; C. Mardsen "Solvents Guide" -Guide of Solvents-, 2nd edition, Interscience, New York, 1963; McCutcheon's "Detergents and Emulsifiers Annual" - McCutcheon's annual publication of detergents and emulsifiers - MC Publ. Corp., Ridgewood New Jersey; Sisley and Wood "Encyclopedia of Surface Active Agents" - Encyclopedia of Surfactants - Chem. Publ. Inc., New York, 1964; Schonfeldt, "Grenzfláchenaktive Áthylenoxidaddukte" - Ethylene oxide surfactant additives - Wiss. Verlagsgesell, Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie" -Technology chemistry-, volume 7, C. Hauser Verlag Munich, 4th edition, 1986. Wettable powders are preparations that are uniformly dispersible in water and contain, in addition to the active compound and also a diluent or inert substance, ionic and / or nonionic surfactants (wetting agents, dispersants), for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol polyglycol ether sulphates, alkane sulphonates, alkylbenzene sulphonates, sodium lignin sulfonate , 2,2'-dinaphthylmethane-6-6'- 5-sodium disulfonate, sodium dibutylnaphthalene sulfonate or sodium oleoylmethyltaurinate. To prepare the wettable powders, the herbicidally active compounds are finely milled, for example in the usual apparatuses such as hammer mill, fan mills and air jet mills, and are mixed simultaneously or subsequently with the formulation aids. Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or relatively high-boiling aromatic compounds, or hydrocarbons or mixtures thereof. organic solvents, with the addition of one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used are calcium alkylaryl sulfonates such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, polyglycol ethers of fatty alcohol, condensation products of propylene oxide-ethylene oxide, alkylpolyethers, sorbitan esters, for example sorbitan fatty acid esters or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.

^^^^^. Dusting powders are obtained by grinding the active compound with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. The suspension concentrates can be water or oil based. They can be prepared, for example, by wet milling using commercially usual ball mills, with or without the addition of surfactants as already mentioned above for example in the case of other types of formulation. Emulsions, for example oil-in-water (EW) emulsions, can be prepared by means of stirrers, colloid mills and / or static mixers, using aqueous organic solvents and, if desired, surface-active agents, as mentioned above for example in US Pat. case of other types of formulation. Granules can be prepared either by sprinkling the active compound on an inert granulated adsorbent material, or by applying concentrates of the active compound to the surface of vehicles such as sand, kaolinites or granulated inert material by means of adhesive binders, for example polyvinyl alcohol, sodium polyacrylate or mineral oils. Suitable active compounds can also be granulated in the usual manner for the preparation of fertilizer granules, if desired, as a mixture with fertilizers. The water-dispersible granules are generally prepared by the usual methods, such as spray drying, fluidized bed granulation, disk granulation, mixing using high speed mixers, and extrusion without inert solid material. For the preparation of disk granules, fluidized bed, extruder and sprinkler, see the procedures, for example in "Spray-Drying Handbook" - Handbook for spray drying - 3rd edition, 19J9, G. Goodwin Ltd., London; J.E. Browning "Agglomeration" Chemical and Engineering -Aglomeration, Chemistry and Engineering- 1967, pages 147 et seq .; "Perry's Chemical Engineer's Handbook"-Perry's Chemical Engineering Manual-, 5th ed. McGraw-Hill, New York 1973, pages 8-57. For more details on the formulation of crop protection products, see for example G.C. Klingman, "Weed Control as a Science" -Weed control as a science- John Wiley and Sons Inc., New York, 1961, pages 81-96, and J.D. Freyer, S.A. Evans, "Weed Control Handbook" -Weed Control Manual- 5th edition, Blackwell Scientific Publications, Oxford, 1968, pages 101-103. The agrochemical formulations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of active compound of formula I. In wettable powders, the concentration of active compound is, for example, approximately 10 to 90% by weight, the rest consisting of 100% by weight of usual formulation constituents. In emulsifiable concentrates, the concentration of active compound can be about 1 to 90%, preferably 5 to 80% by weight. Formulations in the form of powders contain from 1 to 30% by weight of active compound, most preferably from 5 to 20% by weight of active compound, while the sprayable solutions contain about 0.05 to 80%, preferably 2 to 50% by weight of active compound. In the case of water-dispersible granules, the content of active compound depends partly on whether the active compound is in liquid or solid form, and on the granulation auxiliaries, fillers, etc., that are used. In water-dispersible granules, the content of active compound is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight. In addition, said formulations of active compound may comprise thickeners, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, vehicles, dyes, defoamers, evaporation inhibitors and pH and viscosity regulators, which are customary in each case. On the basis of these formulations, it is also possible to produce combinations with other pesticidally active substances, for example insecticides, acaricides, herbicides and fungicides, and also with safety agents, fertilizers and / or growth regulators, for example in the form of a mixture. Ready to use or a tank mix. Suitable active ingredients which can be combined with the active ingredients according to the invention in mixed formulations or in a tank mixture are, for example, active ingredients ÉÉMMÉÉ known as those described for example in Weed Research 26, 441-445 (1986), or in "The Pesticide Manual" -The pesticide manual- 11th edition, The British Crop Protection Council and the Royal Soc. Of Chemistry , 1997, and in the literature cited therein. For example, the following active ingredients can be mentioned as herbicides which are known and which can be combined with the compounds of formula I (note: the compounds are named by their "common name" according to the International Organization for Standardization (ISO)) , or by its chemical name, if appropriate along with a usual code number): acetochlor; acifluorfen, aclonifen, AKH 7088, that is, [[[1-t5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidene] amino] oxy] -acetic acid and its methyl ester; alachlor, alloxydim, ametryn, amidosulfuron, amitrol, AMS, that is, ammonium sulfamate; anilophos, asulam, atrazine, azimsulfuron (DPX-A8947), aziprotryn, barban, BAS 516H, ie 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one, benazolin, benfluralin, benfuresate, bensulfuron -methyl, bensulide, bentazone, benzofenap, benzofluor, benzoylpro'p-ethyl, benzothiazuron, bialaphos, bifenox, bromacil, bromobutide, bromophenoxy, bromoxilin, bromuron, buminaphos, busoxinone, butachlor, butamiphos, butenachlor, butidazole, butralin, butylate, cafenstrole (CH-900), carbetamide, cafentrazone (ICI-A0051), CDAA, i.e., 2-chloro-N, N-di-2-propenylacetamide; CDEC, that is, 2-chloroalyl-diethyldithiocarbamate, clometoxifen, chloramben, clorazifop-butyl, chlormesulon (ICI-A0051), chlorbromuron, chlorbufam, chlorfenac, chlorflurecol-methyl, chloridazon, chlorimuron ethyl, clomitrofen, chlorotoluron, chloroxuron, chlorprofam, chlorsulfuron , chlortal-dimethyl, clortiamid, cinmethilin, cinosulfuron, clethodim, clodinafop and its ester derivatives (eg clodinafop-propargiulo), clomazone, clomeprop, cloproxidim, clopyralid, cumiluron (JC 940), cyanazine, cycloate, cyclo-sulphanuron (AC 104), cycloxydim, cycluron, cyhalofop and their ester derivatives (for example butyl ester, DEH-112); cyperquat, ciprazine, ciprazole, daimuron; 2,4-DB; dalapon, desmedifam, desmethrin, di-alato, dicamba, diclobenil, dicloprop, diclofop and its esters such as diclofop-methyl, dietyl, difenoxuron, difenzoquat, diflufenican, dimefuron, dimethachlor, dimethamethrin, dimethenamid (SAN-582H), dimetazone, clomazon , dimetipin, dimetrasulfuron, dinitramine, dinoseb, dinoterb, diphenamid, dipropetrin, diquat, dithiopyr, diuron, DNOC, eglinazine-ethyl, EL 77, that is, 5-cyano-1- (1,1-dimethylethyl) -N- meth1-1 Hp-aceol-4-carboxamide; endothelium, EPTC, esprocarb, etalfluralin, etametsulfuron-methyl, etidimuron, etiozin, etofumesate, F5231, ie N- [2-chloro-4-fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro -5-oxo-1 H-tetrazol-1-yl] phenyl] ethanesulfonamide; ethoxyfen and its esters (for example ethyl ester, HN-252); etobenzanid (HW 52), fenoprop, fenoxan, fenoxaprop and fenoxaprop-P and their esters, for example fenoxaprop-P-ethyl and fenoxaprop-ethyl; phenoxydim, fenuron, flamprop-methyl, flazasulfuron, fluazifop and fluazifop-P and their esters, for example fluazifop-butyl and fluazifop-P-butyl; flucloralin, flumetsulam, flumeturon, flumiclorac and their esters (for example pentylester, S-23031); flumioxazin (S-482), flumipropin, flupoxam (KNW-739), fluorodifen, fluoroglycofen-ethyl, flupropacil (UBIC-4243); fluoridone, flurocloridone, fluroxypyr, flurtamone, fomesafen, fosamine, furiloxifen, glufosinate, glyphosate, halosafen, halosulfuron and their esters (for example methyl ester, NC-319); haloxifop and its esters; haloxifop-P (= R-haloxifop) and its esters; hexazinone, imazametabenz-methyl, imazapyr, mazaquin and its salts such as the ammonium salt; imazetametapir, mazetapir, mazosulfuron, 5 ioxinil, socarbamid, isopropalin, isoproturon, isouron, soxaben, isoxapirifop, karbutylate, lactofen, lenacil, linuron, MCPA, MCPB, mecoprop, mefenacet, mefluidid, metamitron, metazachlor, metabenzothiazuron, metam , metazole, methoxyphenone, methyldimiron, methobenzuron, methobromuron, metolachlor, metosulam (XRD 511), methoxuron, metribuzin, metsulfuron-methyl, MH, molinate, monalide, monocarbamide diacid sulfate, monolinuron, monuron, MT 128, i.e. -chloro-N- (3-chloro-2-propenyl) -5-methyl-N-phenyl-3-pyridazinamine; MT 5950, ie N- [3-chloro-4- (1-methylethyl) phenyl] -2-methylpentanamide; naproanilide, napropamide, naptalam, NC 310, ie, 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxy pyrazole; neburon, nicosulfuron, nipiraclofen, nitralin, nitrophen, nitrofluorfen, norflurazon, orbencarb, orizalin, oxadiargil (RP-020630), oxadiazon, oxyfluorfen, paraquat, pebulate, pendimethalin, perfluidone, fenisofam, fenmedifam, picloram, piperophos, pyributicarb, pyrifenop-butyl, pretilachlor, primisulfuron- methyl, procyanine, prodiamine, profluralin, proglinazine-ethyl, promethan, prometrin, propachlor, propanil, propaquizafop and your esters; propazine, profam, propisoclor, propizamide, prosulfalin, prosulfocarb, prosulfuron (CGA-152005), prinachlor, pyrazolinate, pyrazole, pyrazosulfuron-ethyl, pyrazoxyphen, pyridate, piritiobac (KIH-2031), piroxofop and their esters (for example propargyl ester); quinclorac, quinmerac, quinofop and their METHYLERY ester derivatives, quizalofop and quizalofop-P and their ester derivatives, for example, quizalofop-ethyl, quizalofop-P-tefuryl and -ethyl; renriduron, rimsulfuron (DPX-E 9636); S 275, i.e., 2- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -4,5,6,7-tetrahydro-2H-indazole; secbumeton, sethoxydim, siduron, simazine, symmetry, SN 106279, ie, 2 - [[7- [2-chloro-4- (trifluoromethyl) -phenoxy] -2-naphthalenyl] oxy] propanoic acid and its methyl ester; sulfentrazon (FMC-97285, F-6285), sulfazuron, sulfometuron-methyl, sulfosate (ICI-A0224), TCA, tebutam (GCP-5544), tebutiuron, terbacil, terbucarb, terbuclor, terbumeton, terbutilazine, terbutrin, TFH 450, that is, N, N-diethyl-3 - [(2-ethyl-6-methylphenyl) sulfonyl] -1H-1, 2,4-triazole-1-carboxamide; tenilchlor (NSK-850), thiazafluron, thiazopyr (Mon-13200), thidiazimine (SN-24085), thifensulfu rum-methyl, thiobencarb, thiocarbazyl, tralkoxydim, tri-alato, triasulfuron, triazophenamide, tribenuron-methyl, triclopyr, tridifone, trietazine, trifluralin, triflusulfuron and their esters (for example methyl ester, DPX-66037); trimeturon, tsitodef, vernolate, WL 110547, i.e., 5-phenoxy-1- [3- (trifluoromethyl) phenyl] -1 H-tetrazole; UBH-509, D-489, LS 82-556, KPP-300, NC-324, NC-330, KH-218, DPX-N8189, SC-0774, DOWCO-535, DK-8910, V-53482, PP -600, MBH-001, KIH-9201, ET-751, KIH-6127 and KIH-2023. To use the present formulations in commercially available form, they are diluted, if appropriate, in the customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water dispersible granules. Products in the form of powders, granules for application to the ground or broadcast, and sprayable solutions, are not further diluted with other inert substances before use. The required application rate of the compounds of formula I varies with external conditions, such as temperature, humidity, the nature of the herbicide used and the like. It can vary within wide limits, for example, between 0.001 and 10.0 kg / ha or more of active substance, but preferably between 0.005 and 5 kg / ha. The following examples illustrate the invention.

A. CHEMICAL EXAMPLES 1. Preparation of 2-amino-4-fluoro-isopropyl-6-yN- (1-methyl-3-phenoxy-prop-1-yl) aminol-1, 3,5-triazine (see Table 2) Example No. 368) 0.45 g (0.019 mole) of sodium was dissolved in 50 ml of anhydrous methanol. 1.85 g (0.006 mole) of 3-biguanido-1-phenoxybutane hydrochloride were added, followed by 1.3 g (0.010 mole) of ethyl fluoroisobutyrate. The mixture was refluxed for 3 hours. The solvent was removed under reduced pressure and the residue was taken up in dichloromethane / water and extracted repeatedly. The organic phase was dried over MgSO4 and filtered, and the solvent was removed under reduced pressure. Purification by silica gel column chromatography using ethyl acetate / heptane (1: 1) gave 0.45 g (24%) of the title compound. 2. Preparation of 2-amino-4-isopropyl-6- (N-1-methyl-2- (4-chlorobenzyloxy) ethyl-1-ylene} -1, 3,5-triazine (see Table 1, Example No. 166) 1.00 g (0.004 mole) of 2-aminopropyl 4-chlorobenzyl ether hydrochloride was initially charged together with 2.34 g (0.017 mole) of potassium carbonate and 0.73 g (0.004 mole) of 2 -amino-4-chloro-6-isopropyl-1, 3,5-triazine, and the mixture was refluxed for 3 hours.The solvent was removed under reduced pressure and the residue was taken up in ethyl acetate / water and The organic phase was dried over MgSO 4 and filtered, and the solvent was removed under reduced pressure, purification by silica gel column chromatography using ethyl acetate / heptane (1: 1). 1.20 g (89%) of the title compound. 3. Preparation of 2-amino-4-isopropyl-6- (N-1,2- (3,4-dichlorobenzoyl-oxy) ethyl-amino) -1,5-triazine. Initially, 0.5 g (0.0024 mol) of chloride was charged. of 3,4-dichlorobenzoyl in 30 ml of 1,4-dioxane and 0.47 g (0.0024 mole) of 2-amino-4-isopropyl-6- [N- (2-hydroxyethyl) amino-1, 3,5-triazine , and 0.483 g (0.005 moles) of triethylamine were added. The mixture was refluxed for 4 hours. The precipitated solid was removed by filtration and the solvent was removed under reduced pressure. The residue was taken in ethyl acetate / water and extracted repeatedly. The organic phase was dried over MgSO4 and filtered; the solvent was removed under reduced pressure. This gave 0.65 g (73%) of the title compound. nMÉUIMtfÉfiMÉKáit? iH iÚÚMEMBODÜH The examples listed in the following tables were prepared by the methods mentioned above, or can be obtained by the methods mentioned above. The meanings of the abbreviations used in the tables are as follows: Et = ethyl Me = methyl c = cycle n = normal i = iso s = secondary t = tertiary p.f. = melting point In the context of the tables, an asymmetric divalent group Y, such as Y = C (0) 0 (ie, -CO-0-) is a group in which the point of attachment of the group atom shown on the left, is attached to the molecular portion shown, in formula (I), to the left of Y. _.- aiMaiM? ^ TABLE 1 Compounds of formula (la) (= formula I where n = 1 and R1, R2, R5, R7, R9, R10, are each H and aryl phenyl which is substituted as indicated in picture) fifteen twenty TABLE 2 Compounds of formula (Ib) (= formula I where n = 2, R1, R2, R3, R5, R7, R9, R10, are each hydrogen and aryl = phenyl which is substituted as indicated in the table) lrfkriÉÉlÁ¿ ^ ¿10 fifteen twenty uttßta ^^^ UÉHÜ H 10 fifteen twenty «MtoÉüiÉliliMiÉiiU.

TABLE 3 Compounds of formula (le) (= formula I where n = 3, R1, R2, R5, R7, R9, R10, are each hydrogen and aryl = phenyl which is substituted as indicated in the table) (you) fifteen twenty iflilUÉÉMi 10 fifteen ^^^? ^^^^? L ^ agg g ¡m? MÉMÉMMÉiiliDHMIMll fifteen TABLE 4 Compounds of formula (Id) (= formula I where n = 4: R1, R2, R5, R7, R9 and R10 are each hydrogen and aryl = phenyl which is substituted as indicated in the table ) (Id) fifteen M ^ MüAÜÉIIÉÜÉilildMi ^^ ^ urimiiitfitiiii 10 ^ ateMdK ^ | B | U? Mj & ^^ yjy ^ t ^^ TABLE 5 Compounds of formula (le) (= formula 1 where n = 5, R1, R2, R5, R7, R9 and R10 are each hydrogen and aryl = phenyl which is substituted as indicated in the box) TABLE 6 Compounds of formula (If) (= compounds of formula (I) where m = 0. Y = O, (CR3R4) n-CR5R6 = cyclohexane-1,3-diyl, R7 = H, R9 = H and aryl = phenyl which is substituted as indicated in the table) , ¿? " I TABLE 7 Compounds of formula (Ig) (= compounds of formula (I) wherein m = 0, Y = O. (CR3R4) n-CR5R6 = • CH2-1.2-cycloCfiH? N-, R7 = R9 = R10 = H and aryl = phenyl which is substituted as indicated in the table) (ig) TABLE 8 Compounds of formula (Ih) (= formula (I) wherein m = 0, Y = O, (CR3R4) n-CR5R6 = -CH2-1,2-cyclopentyl-, R7, R9, R10 are each H , and aryl = phenyl which is substituted as indicated in the table) TABLE 9 Compounds of formula (Ik) formula (I) wherein m = 1. n = 1. R1 and R2 are each H, (CR3R4) carbonyl; R5, R7. R9, R10 are each H, and aryl = phenyl which is substituted as indicated in the table) fifteen twenty riMI ^ iÉiikailÉHMUb TABLE 10 Compounds of formula (Im) (= formula (I) where m = 0. n = 1. Y = -NH-CO-NH-, IR3 and R4 are each H: R5, R7, R9 , R10 are each H, and aryl = phenyl gtie is substituted as indicated in the table) MMAHIÁ TABLE 11 Compounds of formula (In) (= formula (I) where m = 0, n = 1. Y = -NH-CO-O-, R3 and R4 are each H; R > 5. R. R, 9, D R10 are each H, and aryl = phenyl which is substituted as indicated in the table) ik ^^ ii ^ hlHlHHÉl aaaB ^ l_Í_ ^ | ^^ M > U 10 fifteen 10 tfdhÉÉyádi ^ l ^ dta TABLE 12 Compounds of formula (lo) (= formula (I) where m = 1. n = 1. Y = -ON =. R3 = point of union for double bond, R4 = H: R5. R7, R9, R10 are each H. and aryl = phenyl which is substituted as indicated in the table) fifteen twenty ÉjaaM | ri ^ afl | Mw | Éi || TABLE 13 Compounds of formula (Ip) (= formula (I) where m = 0, n = 1. Y = -O- (CH2)? - O-, R3 = H. R4 = H, R5 = H; R »7, r R» 9, D R10 are each H, and aryl = phenyl which is substituted as indicated in the table) fifteen twenty ^^ Hlé &ÜB 10 fifteen twenty B. EXAMPLES OF FORMULATION 1. Sprinkling agent A sprinkling agent is obtained by mixing 10 parts by weight of a compound of formula (I) and 90 parts by weight of talc as an inert substance and grinding the mixture in a hammer mill. 2. Dispersible Powder A wettable powder, easily dispersible in water, is obtained by mixing 25 parts by weight of a compound of formula (I), 64 parts by weight of quartz containing kaolin as an inert substance, 10 parts by weight of potassium lignin sulfonate and 1 part by weight. part by weight of sodium oleoylmethyltaurinate as a wetting and dispersing agent, and grinding the mixture in a spiky disk mill. 3. Dispersible concentrate A concentrate easily dispersible in water is obtained by mixing 20 parts by weight of a compound of formula (I), 6 parts by weight of polyglycol ether of alkylphenol (RTriton X 207), 3 parts by weight of polyglycol ether of isotp'decanol (8 EO) and 71 parts in pee of paraffinic mineral oil (boiling range, for example, from about 255 to over 277 ° C), and grinding the mixture in a ball mill to a fineness of less of 5 microns. dtAMßttil 4. Emulsifiable concentrate An emulsifiable concentrate of 15 parts by weight of a compound of formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as an emulsifier is obtained.

. Water-Dispersible Granules Water-dispersible granules are obtained by mixing: 75 parts by weight of a compound of formula (I), 10 parts by weight of calcium lignin sulphonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol , and 7 parts by weight of kaolin, grinding the mixture in a spiky disk mill and granulating the powder in a fluidized bed and watering it as a granulation liquid. Water-dispersible granules are also obtained by homogenising and milling in advance in a colloidal mill: 25 parts by weight of a compound of formula (I), 5 parts by weight of sodium 2,2-dinaphthylmethane-6,6'-disulfonate, 2 parts by weight of sodium oleoylmethyltaurinate, 1 part of polyvinyl alcohol, 17 parts of calcium carbonate, and 50 parts of water, followed by milling in a bead mill, and atomizing and drying the resulting suspension in a spray tower using a nozzle of a single substance.

C. BIOLOGICAL EXAMPLES 1. Preemergence action against weeds Seeds of mono- and dicotyledonous weed plants are placed on sandy mud soil in cardboard pots, and covered with soil. The novel compounds, formulated as wettable powders or emulsifiable concentrates, are then applied to the surface of the soil in the form of an aqueous suspension or emulsion at an application rate of 600 to 800 I of water / ha (converted), in various doses . After the treatment, the pots are placed in a greenhouse and kept under good growing conditions for the weeds. After the test plants have emerged after a trial period of 3 to 4 weeks, the damage to the plants or the negative effect on emergence is visually scored by comparison with untreated controls. As shown by the test results, the novel compounds have good preemergence herbicidal activity against a broad spectrum of grasses and broadleaf weeds. For example, the compounds of Examples Nos. 41, 42, 64, 76, 78, 120, 167, 183, 201, 207, 213, 220, 222, 228, 231, 245, 253, 281, 282, 297, 299, 300, 303, 305, 308, 311, 326, 329, 336, JJfl 339, 340, 347, 358, 368, 369, 370, 372, 376, 380, 381, 384, 394, 490, 501, 510, 528, 531, 532, 553, 554, 582, 598, 605, 609 , 618, 626, 636, 645, 681, 696, 698, 869, 870, 926, 930, 987, 1005, 1234, 1235, 1236, 1251, 1252, 1253, 1307, 1344, 1345, 1346, 1364, 1385 and 1404, show good and, in most cases very good, herbicidal activity against noxious plants such as Stellaria media, Amaranthus retroflexus, Sinapis avreuse, Avena fatura, Lolium multiflorum and Setaria virídis, at an application rate of 3.0 kg or less active substance per hectare. 2. Post-weed action against weeds Seeds of mono- and dicotyledonous weeds are placed in sandy mud soil in cardboard pots, covered with soil and cultivated in a greenhouse under good growth conditions. Two to three weeks after sowing, the test plants are treated in the three-leaf stage. The novel compounds, formulated as wettable powders or emulsifiable concentrates, are sprayed in several doses on the green parts of the plant, at an application rate of 600 to 800 I of water / ha (converted) and, after the plants have remained in the greenhouse for 3 to 4 weeks under optimal growth conditions, the action of the preparations is visually qualified by comparison with untreated controls. The novel compounds also have good post-emergence herbicidal activity against a broad spectrum of economically important broadleaf grasses and weeds. For example, ^ d UÉßA compounds of examples Nos. 20, 23, 41, 42, 43, 46, 78, 80, 183, 184, 201, 207, 213, 220, 222, 228, 231, 245, 253, 281, 297 , 299, 303, 305, 308, 311, 326, 336, 340, 347, 358, 368, 369, 370, 372, 376, 380, 381, 384, 490, 501, 502, 510, 528, 531, 532 , 553, 554, 582, 598, 605, 609, 618, 626, 636, 645, 681, 696, 698, 869, 870, 926, 930, 987, 1005, 1234, 1235, 1251, 1252, 1253, 1307 , 1344, 1345, 1346, 1364, 1385 and 1404, show good, and in most cases very good, herbicidal activity against harmful plants such as Stellaria media, Amaranthus retroflexus, Sinapis avreuse, Avena fatura, Lolium multiflorum and Setaria viridis , at an application rate of 3.0 kg or less of active substance per hectare. 3. Action on weeds in rice Typical weeds of rice such as Echinocloa crus galli and Cyperus iría are cultivated in a greenhouse under paddy rice conditions (stagnant water height: 2-3 cm). After the treatment, the test plants are placed in a greenhouse under optimal growth conditions and are kept in this form under these conditions throughout the period of the test. About three weeks after the application, evaluation is made by visual qualification of the damage to the plants by comparison with untreated controls. The compounds according to the invention have very good herbicidal activity against harmful plants. For example, compounds Nos. 41, 42, 46, 120, 183, 201, 207, 213, 220, 222, 228, 231, 245, 253, 281, 299, 300, 303, 308, 311, 326, 336 , 340, 347, 358, 368, 369, 370, 372, 376, 380, 381, 384 and 394, show very good herbicidal activity against Cyperus iría and Echinocloa crus-galli. 4. Tolerance of crop plants 5 In additional greenhouse experiments, seeds from a relatively large number of cultivation plants are placed in sandy mud soil, and covered with soil. Some of the pots are treated immediately as described in section 1, while the rest are placed in a greenhouse until the plants have developed two to three true leaves, and then sprayed with several doses of the novel formula substances (I) as described in section 2. Four to five weeks after the application, and after the plants have remained in the greenhouse, a visual rating shows that the compounds according to the invention leave intact or almost intact the dicotyledonous crops such as soybean and sugar beet, when used pre- and post-emergence, even when high doses of active compound are used. In addition, some substances also leave gram culture intact, for example barley, wheat and rice. Some of the compounds of formula (I) exhibit high selectivity and therefore are suitable for controlling the growth of unwanted plants in agricultural crops. - • * - '"- *» ** ~ ** - * «•.

Claims

NOVELTY OF THE INVENTION CLAIMS

1. - A compound of formula I, also in its salt form, if appropriate, wherein Aril is a substituted or unsubstituted mono- or bicyclic aromatic radical having from 5 to 14 ring atoms, 1, 2, 3 or 4 of which may, in each case independently of one another, originate from the group consisting of of oxygen, sulfur and nitrogen; -Y- is a divalent unit of the group consisting of -O-, -S-, -NR11-, -NR12CONR13-, -C02-, -OC02-, -OCONR14-, -SO-, -S02-. -S020-, -OS020-, -S02NR14-, -O-NR11, -NR'-NR "-, wherein R 'and R", independently of one another, are as defined for R14, and - (Y' -CRaRb-CRcRd); -Y ", where Y 'and Y" are, independently of one another, O, S, NH or N [d-C4 alkyl], Ra, Rb, Rc and Rd are in each case, independently of each other, H or C? -C alkyl, ei is an integer from 1 to 5, or a trivalent unit of formula -0-N =; m is 0, 1, 2, 3, 4 or 5; n is an integer from 1 to 10, with the proviso that n is not 1 if rn is zero and -Y- is -O-, -S-, -SO-, -S02- or -NR11-; R1, R2 in each case, independently of one another, is a radical of a group G1 comprising hydrogen, CiC-io alkyl, C2-C8 alkenyl, C2-Cs alkynyl, C1-C10 alkoxy, C3 cycloalkyl -C8, C3-Cs cycloalkoxy, arylalkyl of C-pCβ and cycloalkyl (C3-C8) -alkyl of Ci-Cβ, wherein the cyclic portion of the last four mentioned radicals, in each case is unsubstituted or substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X1, wherein -B- and X1 are as defined below, and wherein the non-cyclic portion of the last eight radicals mentioned of the group G1, in each case, is unsubstituted or substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X2, wherein X2 is as defined below, and wherein the non-cyclic portion of the radicals of group G1 may, in each case, be interrupted with one or more heteroatoms identical or different from the group consisting of oxygen and sulfur, R1 and R2 of a group (CR1R2) form, together with the carbon atom carrying a carbonyl group, a group CR15R16 or a ring of 3 to 6 members which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X1, or two R1 of two groups (CFR1 R2) directly adjacent or not directly adjacent, together with the carbon atoms that carry or bind them, form an unsubstituted or substituted 3 to 6-membered ring may contain one or two different heteroatoms of the group . . ". *» »... . ", *., ..»,. ....,. .. which consists of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X1, or two R1 of two groups ( CR1R2) directly adjacent, together with the bond between the carbon atoms of the groups, form a double bond, or two R1 and two R2 of two groups (CR1R2) directly adjacent, together with the bond between the carbon atoms of the groups , form a triple bond, or R1 is a point of attachment for the double bond in the case where Y is a trivalent unit = N-0-adjacent to a group CR1R2; R3, R4 in each case, independently of one another, is a radical of a group G2 comprising hydrogen, alkyl of CIC-IO, alkenyl of C2-Cs, alkynyl of C2-Cs, alkoxy of C1-C10, alkylthio of CiC -io, C 1 -C 0 alkylsulfinyl, C 1 -C 10 alkylsulfonyl, C 3 -C 8 cycloalkyl, C 3 -C 6 cycloalkoxy, aryl, C 1 -C 6 arylalkyl, Ci-C 1 arylalkoxy, C 3 -C 8 cycloalkyl -alkyl C Cß, (C3-C8) cycloalkyl-Ci-Cβ alkoxy, (C3-C8) cycloalkoxy-C-Cß alkyl, and Cc-C6-C6-C8-alkoxy-C6alkoxy, wherein the cyclic portion of the last nine mentioned radicals, in each case, is not substituted or is substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X1, in where -B- and X1 are as defined below, and wherein the non-cyclic portion of the last sixteen mentioned radicals of the group G2, in each case, is unsubstituted or is substituted with one or more identical or different radicals of the group which consists of halogen, nitro, cyano, thiocyanate and -B-X2, wherein X2 is as defined below, and wherein the non-cyclic portion tfWMáHfaiütfaiittfc «H ^^^^ aillÉ Ma of the radicals of group G2 may be, in each case, interrupted by one or more heteroatoms identical or different from the group consisting of oxygen and sulfur, or R3 and R4 together with the carbon atom which carries them, form a carbonyl group, a CR15R16 group or a 3 to 6 member ring, which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X1, or two R3 of two groups (CR3R4) directly adjacent or not directly adjacent, together with the carbon atoms that carry or link them, form a 3 to 6 membered unsubstituted or substituted ring, which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or is not substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X1; or two R3 of two groups (CR3R4) directly adjacent, together with the bond between the carbon atoms of the groups, form a double bond, or two R3 and two R4 of two groups (CR3R4) directly adjacent, together with the bond between the carbon atoms of the groups form a triple bond, or R3 is a point of attachment for the double bond in the case where Y is a trivalent unit -0-N = adjacent to a group CR3R4, -B- is a direct bond or a divalent unit of the group consisting of -O-, -S-, -NR11-, -NR12CONR13-, -C02-, -0C02-, -OCONR14-, -SO-, -S02-, -S020 -, -OS020-, and -S02NR14-; X1 is hydrogen, C-alkyl id EHhtUí Cß, C2-Cß alkenyl, C2-Cs alkynyl, C3-Cs cycloalkyl or heterocyclyl having from 3 to 9 ring atoms, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen and sulfur, and wherein the last five mentioned radicals are unsubstituted or substituted with one or more identical or different halogen atoms; X2 is hydrogen or heterocyclyl having from 3 to 9 ring atoms, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen and sulfur, which is unsubstituted or substituted with one or more halogen atoms identical or different; R5, R6 independently of one another, is a radical of the group G2, or R3 and R5 of two groups (CR3R4) or (CR5R6), directly adjacent or not directly adjacent, together with the carbon atoms that link them, form a ring 3 to 6 members unsubstituted or substituted which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of of halogen, nitro, cyano, thiocyanate and -B-X1, or R5 and R6 together with the carbon atom carrying them, form a carbonyl group, a group CR15R16 or a ring of 3 to 6 members which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X1, or R6 is heterozy clilo; R7 is hydrogen, amino, alkylcarbonyl, alkylamino or dialkylamino, which in each case has ^^ d * Eb one to six carbon atoms in the alkyl radical, is an acyclic hydrocarbon radical or hydrocarbonoxy having in each case from one to six carbon atoms, is a cyclic hydrocarbon radical or hydrocarbonoxy having in each case three to six carbon atoms, or is heterocyclyl, heterocyclyloxy or heterocyclylamino having in each case from three to six ring atoms and from one to three ring heteroatoms of the group consisting of nitrogen, oxygen and sulfur; wherein each of the last ten mentioned radicals is unsubstituted or substituted with one or more radicals identical or different from the group consisting of halogen, C1-C4 alkoxy, halo-C1-C4 alkoxy, C1-C4 alkylthio, C2-C4 alkenyl, C2-C4 alkynyl, C2-C4 alkenyloxy, C2-C4 alkynyloxy, hydroxyl, amino, acylamino , alkylamino, dialkylamino, nitro, carboxyl, cyano, azido, C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, formyl, carbamoyl, mono- and dialkyl (C -? - C4) aminocarbonyl, C1-C4 alkylsulfinyl, halo - C 1 -C 4 alkyl sulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl and, in the case of cyclic radicals, also C 1 -C 4 alkyl and halo C 1 -C 4 alkyl, R 8 is C 1 -C 4 alkyl C10, C2-C8 alkenyl, C2-Cs alkynyl, which are unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, cyano, nitro, thiocyanate, hydroxyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, phenyl, C3-Cg cycloalkyl, C3-C3 cycloalkoxy, and is heterocyclyl having three to six ring atoms and one or to three ring heteroatoms of the group consisting of oxygen, nitrogen and sulfur, which is unsubstituted or is MtHüteah substituted with one or more radicals identical or different from the group consisting of halogen, amino, C 1 -C 4 alkyl, C 4 -C 4 alkoxy, C 1 -C 4 haloalkyl and C 1 -C 4 haloalkoxy, is C3-C8 cycloalkyl, C3-C3 cycloalkoxy or a heterocyclyl radical having from three to six ring atoms, wherein these last three radicals are unsubstituted or substituted with one or more radicals identical or different from the group consists of halogen, nitro, cyano, thiocyanate, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halo C 1 -C 4 alkyl and halo C 1 -C 4 alkoxy; R9, R10 each independently of one another, is hydrogen, amino, C1-C10 alkylcarbonyl, C1-C10 alkylamino, C? -C10 dialkylamino, C10-C10 alkyl, C3-Cs cycloalkyl, alkoxy of C C10, C3-Cβ cycloalkoxy, heterocyclyl, heterocyclyloxy or heterocyclylamino having in each case from 3 to 6 ring atoms and from 1 to 3 ring heteroatoms of the group consisting of oxygen, nitrogen and sulfur, wherein each one of the last ten mentioned radicals is unsubstituted or substituted, or R9 and R10 together with the nitrogen atom that bears them, form a heterocycle having a total of three to six ring atoms, and among these, one to four ring heteroatoms, wherein the other ring heteroatoms which may be present in addition to the nitrogen atom that is present, are selected from the group consisting of oxygen, nitrogen and sulfur, and wherein this heterocycle is unsubstituted or is replaced, R 11 is hydrogen, amino, C1-C10 alkylamino, dialkylamino of C-i-C-, C1-C10 alkyl. C3-Cβ cycloalkyl, (C3-C8) cycloalkyl-C-i-Cß alkyl. CrC10 alkoxy, (C? -C6) alkoxy-C-i-Cß alkoxy, C3-Cs cycloalkoxy, C1-C10 alkylcarbonyl, wherein the -, < ^ -, a to > . ^ > . ... ... "im ***» ,,.,. ,. ^ ¿¿¿. 1. ^. . .. .., .. I. - «w. ", .... The last nine mentioned radicals are unsubstituted or substituted, R12, R13 each, independently of one another, is hydrogen, C1-C10 alkyl, C2-Cs alkenyl, C2-C8 alkynyl, phenyl, phenylalkyl of C-. -C6, C3-Cs cycloalkyl, (C3-C8) cycloalkyl-CrC6 alkyl, wherein the cyclic portion of the last four mentioned radicals, in each case, is unsubstituted or substituted with one or more identical or different radicals of the group consisting of C 1 -C 4 alkyl, halo C 1 -C 4 alkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy, or R 12 and R 13 together with the N-CO-N group bearing them, they form a ring of 5 to 8 members which, in addition to the two nitrogen atoms mentioned above, can contain an additional heteroatom of the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted, R14 is hydrogen or alkyl of C1-C10 or C3-C-io cycloalkyl, unsubstituted or substituted in each case, and R15, R16 ind independently of one another, it is hydrogen, aryl, C 1 -C 10 alkoxy, arylalkyl Ci-Cß, alkyl C 1 -C 10, alkylthio C 1 -C 10, wherein the last five radicals mentioned are unsubstituted or substituted, and wherein the aliphatic carbon skeleton of the last three radicals mentioned may be interrupted by one or more heteroatoms identical or different from the group consisting of oxygen and sulfur, or R15 and R16, together with the carbon atom carrying them, form a ring of 3 to 6 members which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted. MilaiÉliw

2. The compound according to claim 1, further characterized in that Aril is an unsubstituted or substituted mono- or bicyclic aromatic radical having from 5 to 10 ring atoms, 1, 2, 3 or 4 of which in each case, independently of one another, it originates from the group consisting of oxygen, sulfur and nitrogen, and -Y is a divalent unit of the group consisting of -O-, -S-, -NR11-, -NR12CONR13-, -C02-, - OCONR14-, -SO-, -S02-. -S020-, -S02NR14-, -O-NR11, -NH-NH- and -0-CRaRb-CRcRd-0-, wherein Ra, Rb, Rc and Rd are independently of each other, H, CH3 or C2H5, or a trivalent unit of formula -0-N = and R1, R2, are each, independently of one another, a radical of a group G3 comprising hydrogen, C? -C8 alkyl, C2-C6 alkenyl, alkylation of C2-C6, Ci-Cβ alkoxy, C3-C8 cycloalkyl, C3-C8 cycloalkoxy, C6-C6 arylalkyl and C3-C8 cycloalkylC-C alkyl, wherein the cyclic portion of the last four radicals mentioned, in each case, is not replaced or is 15 substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X1, wherein -B- and X1 are as defined below, and wherein the non-cyclic portion of the latter eight mentioned radicals of the group G3, in each case, is unsubstituted or is substituted with one or more radicals identical or different from the group 20 consists of halogen, nitro, cyano and -B-X2, wherein X2 is as defined below, and wherein the non-cyclic portion of the radicals of group G3, in each case may be interrupted with one or more identical heteroatoms or different from the group consisting of oxygen and sulfur, or R and R2 in a group (CR1R2) form, together with the carbon atom carrying them, a carbonyl group, a group CR15R16 or a ring of 3 to 6 members which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X1, or two R1 of two groups (CR1R2) directly adjacent or not directly adjacent , together with the carbon atoms that carry or link them, form a ring of 3 to 6 members, unsubstituted or substituted, which may contain one or two heteroatoms which are identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X1, or two R1 of two groups (CR1R2) directly adjacent, together with the bond between the carbon atoms of the groups form a double bond, or two R 1 and two R 2 of two groups (CR 1 R 2) directly adjacent, together with the bond between the carbon atoms of the groups, form a triple bond or R 1 is a junction point for the double bond in the case where Y is a trivalent unit = N-0- adjacent to a group CR1R2, and R3 and R4 each, independently of each other, is a radical of a group G4 that it comprises hydrogen, Ci-Cs alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C-Cß alkoxy, C3-Cs cycloalkyl, C3-Cß cycloalkoxy, aryl, CrC6 arylalkyl, CrC6 arylalkoxy, cycloalkyl ( C3-C8) -alkyl of C C6, cycloalkyl (C3-C8) -alkoxy of Ci-Cß, cycloalkoxy (C3-C8) -alkyl of C -.- C6 and cycloalkoxy (C3-C8) - rfhMriM Biláh ^ riüß ^^ tfhíÉÉ C? -C6 alkoxy, wherein the cyclic portion of the last nine radicals mentioned, in each case is not substituted or is substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X1, wherein -B- and X1 are as defined below, and wherein the non-cyclic portion of the last thirteen mentioned radicals of the group G4, in each case is not substituted or is substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano, thiocyanate and -B-X2, wherein X2 is as defined below, and wherein the non-cyclic portion of the group G4 radicals may in each case be interrupted by one or two heteroatoms identical or different from the group consisting of oxygen and sulfur, or R3 and R4, June with the carbon atom carrying them, form a carbonyl group, a CR15R16 group or a ring of 3 to 6 members who can e containing one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B- X1, or two R3 of two groups (CR3R4) directly adjacent or not directly adjacent, together with the carbon atoms that carry or link them, form a ring of 3 to 6 members, unsubstituted or substituted, which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X1; or two R3 of two groups (CR3R4) ^^ directly adjacent, together with the bond between the carbon atoms of the groups, form a double bond, or two R3 and two R4 of two groups (CR3R4) directly adjacent, together with the bond between the carbon atoms of the groups, form a triple bond, or R3 is a point of attachment for the double bond in the case where Y is a trivalent unit = N-0- adjacent to a group CR3R4, and -B- is a direct link or a divalent unit of the group consisting of -O-, -S-, -NR11-, -CO-, -C02-, -OC02-, -SO-, -S02-, -S020- and -S02NR14-; X1 is hydrogen, C-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl or heterocyclyl having from 3 to 6 ring atoms, 1, 2 or 3 of which are originate from the group consisting of nitrogen, oxygen and sulfur, and where the last five mentioned radicals are unsubstituted or substituted with one or more identical or different halogen atoms, X2 is hydrogen or heterocyclyl having from 3 to 9 carbon atoms. ring, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen and sulfur, which is unsubstituted or substituted by 1, 2 or 3 identical or different halogen atoms, R5, R6, each, independently of one another, is a radical of the group G4, or R3 and R5 of two groups (CR3R4) - or (CR5R6) -, directly adjacent or not directly adjacent, together with the carbon atoms that link them, form a ring of 3 to 6 members unsubstituted or substituted which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X1, or R5 and R6 , together with the carbon atom carrying them, form a carbonyl group, a CR15R16 group or a 3 to 6 member ring which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or is substituted by one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X1, or R6 is heterocyclyl, and R7 is hydrogen, amino, alkylcarbonyl, alkylamino or dialkylamino, which in each case has from one to four carbon atoms in the alkyl radical, is an acyclic or cyclic hydrocarbon radical having in each case from one to six carbon atoms, or is heterocyclyl having from three to six ring atoms and one at ring heteroatoms of the group consisting of nitrogen, oxygen and sulfur; wherein each of the last six mentioned radicals is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, C1-C4 alkoxy, halo-C1-C4 alkoxy, C-alkylthio. -C4, C2-C4 alkenyl, C2-C alkynyl, C2-C4 alkenyloxy, C2-C4 alkynyloxy, hydroxyl, amino, alkylamino, dialkylamino, nitro, carboxyl, cyano, CC alkoxycarbonyl, C- alkylcarbonyl; -C 4, formyl, carbamoyl, mono- and dialkyl (C 1 -C 4) aminocarbonyl, alkylsulfonyl of C 1 -C 4, haloalkylsulfonyl of C 1 -C 4 and, in the case of cyclic radicals, also C 1 -C 4 alkyl and halo- C 1 -C 4 alkyl, R 8 is C 1 -C 4 alkyl, which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, cyano, nitro, thiocyanate, hydroxyl, C 1 -C 4 alkoxy, C1-C4 alkylthio. C1- alkylsulfonyl ^^ hMÉMHi C, C2-C alkenyl, C2-C4 alkynyl, phenyl, C3-C8 cycloalkyl, C3-C9 cycloalkoxy and heterocyclyl having from three to six ring atoms and from one to three ring heteroatoms of the a group consisting of oxygen, nitrogen and sulfur, which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, amino, C1-C4 alkyl, C1-C4 alkoxy, haloalkyl, C1-C4 and halo-C1-C4 alkoxy; is C3-C8 cycloalkyl or C3-C8 cycloalkoxy) wherein the last two mentioned radicals are unsubstituted or substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano, CrC4 alkyl, C -.- C4 alkoxy, halo-C1-C4 alkyl and halo-C1-C4 alkoxy, R9, R10 each, independently of each other, is hydrogen, amino, alkylcarbonyl of Ci-Ce, Ci-Cβ alkylamino, C? -C6 dialkylamino, CrC6 alkyl, C3-C8 cycloalkyl, Ci-C? alkoxy, C3-C8 cycloalkoxy or heterocyclyl having from 3 to 6 ring atoms and from 1 to 3 ring heteroatoms of the group consisting of oxygen, nitrogen and sulfur, wherein each of the last eight mentioned radicals is unsubstituted or substituted with one or more radicals identical or different from the group consisting of halogen, amino, hydroxyl and, in the case of cyclic radicals, also C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl and C 1 -C 4 haloalkoxy, or R 9 and R 10, together with the nitrogen atom that carries them, they form a heterocycle that has a total of three to six ring atoms and of these, one to four ring heteroatoms, where the other ring heteroatoms which may be present in addition to the nitrogen atom that is present, are selected from the group consisting of oxygen, nitrogen and sulfur, and wherein this heterocycle is unsubstituted or substituted with up to three identical or different radicals from the a group consisting of halogen, amino, hydroxyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halo-C 1 -C 4 alkyl and halo-C 1 -C 4 alkoxy; and R11 is hydrogen, amino, C6 alkylamino, Ci-Cd dialkylamino, C6-C6 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C6-C6alkyl, alkoxy of C? -C6, (C? -C6) alkoxy-Ci-C? alkoxy, C3-C8 cycloalkoxy, C-pC? alkylcarbonyl, wherein the last nine mentioned radicals are unsubstituted or substituted by one 10 or more radicals identical or different from the group consisting of halogen, amino, hydroxyl and, in the case of cyclic radicals, also C 1 -C 4 alkyl, CrC 4 alkoxy, halo C 1 -C 4 alkyl and halo alkoxy of C1-C4, R12, R13 each, independently of one another, is hydrogen, Ci-Cß alkyl, C2-C6 alkenyl, C2-C6 alkynyl, phenyl, phenylalkyl of C-pCβ, cycloalkyl 15 of C3-C8, (C3-C8) cycloalkyl-C6-C6 alkyl, wherein the cyclic portion of the last four mentioned radicals, in each case, is unsubstituted or substituted with one or more identical radicals or different from the group consisting of C -? - C alkyl, CrC4 haloalkyl, C C4 alkoxy and C? -C4 haloalkoxy, or R12 and R13, together with the N-CO-N group bearing them, form 20 a ring of 5 to 8 members which, in addition to the two nitrogen atoms mentioned above, may contain an additional heteroatom of the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more identical radicals or different from the group that aMHlMaiUMilll ÉrifeÜi ^ b consists of halogen, C C alkyl and halo C -C4 alkyl; and R14 is hydrogen or C6 alkyl or C3-C8 cycloalkyl, each of which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, phenyl, hydroxy, d-alkoxy C4, and C1-C4 haloalkoxy, and R15 and R16, each, independently of one another, is hydrogen, phenyl, Ci-Cß alkoxy, phenylalkyl of C-pCβ, C?-C6 alkyl, alkylthio Ci-Cß, wherein the last five mentioned radicals are unsubstituted or substituted, and wherein the aliphatic carbon skeleton of the last three radicals mentioned may be interrupted with one or more heteroatoms identical or different from the group consisting of oxygen and sulfur, or R15 and R16, together with the carbon atom that bears them, form a 3 to 6 member ring which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is not replaced or is replaced with one or more radicals identical or different from the group consisting of halogen, C 1 -C 4 alkyl and halo C 1 -C 4 alkyl.

3. The compound according to claim 1 or 2, further characterized in that Aril is a mono- or bicyclic aromatic radical having 5 to 10 ring atoms, 1, 2, 3 or 4 of which may, in each case , independently of one another, originate from the group consisting of oxygen, sulfur and nitrogen, which is unsubstituted or is substituted with one or more radicals identical or different from the group consisting of halogen, hydroxyl, amino, formyl, C1-6 alkoxycarbonyl. C4, C1-C4 alkylcarbonyl, C1-C4 haloalkoxycarbonyl, C1-C4 haloalkylcarbonyl, C1-C4alkyl, C2-C4alkenyl, C2-C4alkynyl, CCalkoxy, alkoxy (C? -C) -C1-C4 alkyl, halo-alkoxy (CrC4) -CrC4 alkyl > haloalkoxy (C? -C4) - [halo-C1-C4 alkyl], alkoxy (C? -C) - [halo-C1-C4 alkyl], cycloalkyl of C3-C6, 5-cycloalkyl (C3-C6) ) - CrC4 alkyl, (C3-C6) cycloalkyl- [halo-C1-C4 alkyl], halo (C3-C6) cycloalkyl- [halo-C1-C4 alkyl], halo (C3-C6 cycloalkyl) -C1-C4 alkyl, C?-C6 alkylamino C-C6 dialkylamino, d-Cß alkylaminocarbonyl, aminosulfonyl, alkyl (CrC6) aminosulfonyl, dialkyl (C?-Cι-amino-sulfonyl, halo-C 1 -C 4 alkyl and Halo-C1-C4 alkoxy, -Y- is a divalent unit of the group consisting of -O-, -S-, -NR11-, -C02-, -SO-, -S02-, -S020-, - S02NR14-, -NH-CO-NH-, -OCONH-, -O-NH- and -0CH2CH2-0-, or a trivalent unit -0-N =, R1, R2 are in each case, independently of each other, a radical of a group G5 comprising hydrogen, C-C-alkyl, C2-C-alkenyl, C2-C4-alkynyl, C-C6-alkoxy, C3-15 -cycloalkyl Ce, C3-C6-cycloalkoxy, C-arylalkyl -.- C6 and cycloalkyl (C3-C6) -alkyl of C Cß, where the cyclic portion ica of the last four mentioned radicals, in each case, is not substituted or is substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X1, wherein -B- and X1 are as defined below, and wherein the non-cyclic portion of the last eight mentioned radicals of the group G5, in each case, is unsubstituted or is substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X2 , where X2 is as defined below, and where the non-cyclical portion of the ^^^ ¡¡¡¡¡¡¡¡¡¡¡¡^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^ j ^ g ^^^^^^^^^^^^^^^^^^^^^^^ n ^ radical group G5 in each case may be interrupted by one or more identical or different heteroatoms from the group consisting of oxygen and sulfur, or R1 and R2 of a group (CR1R2) form, together with the carbon atom carrying them, a carbonyl group, a CR 5R16 group or a 3 to 5 6-membered ring which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X1, or two R1 of two groups (CR1R2) directly adjacent or not directly adjacent, together with the carbon atoms that carry or link them, form a ring of 3 to 6 members, unsubstituted or substituted, which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nor trógeno and sulfur, and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen, nitro, 15 cyano and -B-X1, or two R1 of two groups (CR1R2) directly adjacent, together with the bond between the carbon atoms of the groups, form a double bond, or two R1 and two R2 of two groups (CR1R2) directly adjacent, together with the bond between the carbon atoms of the groups, form a triple bond or R1 is a point of attachment for the double bond in the 20 case where Y is trivalent unit = N-0- adjacent a CR1R2 group, R3, R4 in each case independently of one another, is a radical of a G6 group consisting of hydrogen, alkyl of C -.- C6, C2-C4 alkenyl, C2-C4 alkynyl, C-C alco alkoxy, C3-C8 cycloalkyl, cycloalkoxy LÉÉMMMHRIM? tfe of C3-C8, aryl, arylalkyl of C C4, arylalkoxy of C1-C4, cycloalkyl (C3-C8) -alkyl of C1-C4, cycloalkyl (C3-C8) -alkoxy of C1-C4, cycloalkoxy (C3 -C8) -alkyl of C? -C4 and cycloalkoxy (C3-C8) -alkoxy of C1-C4, wherein the cyclic portion of the last nine radicals mentioned in each case is unsubstituted or substituted with one or more identical radicals or different from the group consisting of halogen, nitro, cyano and -B-X1, where -B- and X 1 are as defined below, and wherein the portion noncyclic of the last thirteen mentioned radicals of group G6 in each case is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano and -B-X2, where X2 is as in defined below, and wherein the portion of noncyclic the radicals of the group G6 can in each case be interrupted by a heteroatom of the group consisting of oxygen and sulfur, or R3 and R4, together with the carbon atom carrying them, form a carbonyl group, a CR15R16 group or a 3-6 membered ring which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or is substituted with one or more identical or different radicals from the group consisting of halogen, nitro, cyano and -B-X1, or two R3 two groups (CR3R4) directly adjacent or not directly adjacent, together with the carbon atoms that carry or link them, form a ring of 3 to 6 members, unsubstituted or substituted, which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted with up to four identical radicals or ^^^^. different from the group consisting of halogen, nitro, cyano and -B-X1, or two R3 two groups (CR3R4) directly adjacent, together with the bond between the carbon atoms of the groups form a double bond, or two R3 and two R4 of two groups (CR3R4) directly adjacent, together with the bond between the 5 carbon atoms of the groups, form a tiple bond, or R3 is a point of attachment for the double bond in the case where Y is a trivalent unit = N-0- adjacent to a CR3R4 group, and -B- is a direct bond or a divalent unit of the group consisting of -O-, -S-, -NR11-, -CO-, -C02-, -SO-, -S02- and -S02NR14-, X1 is hydrogen, C-C-alkyl, C2-10-C4-alkenyl, C2-C-alkynyl, C3-C6-cycloalkyl or heterocyclyl having from 3 to 6 ring atoms, 1, 2 or 3 of which originates from the group consisting of nitrogen, oxygen and sulfur, and wherein the last five mentioned radicals are unsubstituted or substituted with up to five identical or different halogen atoms, X2 is hydrogen or heterocyclyl which 15 has 3 to 6 ring atoms, 1, 2 or 3 of which originates from the group consisting of nitrogen, oxygen and sulfur, which is unsubstituted or substituted by 1, 2 or 3 identical or different halogen atoms , R5, R6 each, independently of one another, is a radical of the group G6, or R3 and R5 of two groups (CR3R4) - or (CR5R6) -, directly adjacent or not Directly adjacent, together with the carbon atoms that link them, form an unsubstituted or substituted 3 to 6 membered ring which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which do not is replaced or is A liifein substituted with up to four identical or different radicals from the group consisting of halogen, nitro, cyano and -B-X1, or R5 and R6, together with the carbon atom that bears them, forms a carbonyl group, a CR15R16 group or a 3-6 membered ring which may contain one or two heteroatoms 5 identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted by one or more identical or different radicals group consisting of halogen, nitro, cyano, thiocyanate and -B-X1, or R6 is heterocyclyl, and R7 is hydrogen, amyloid, alkylcarbonyl, alkylamino or dialkylamino, which in each case has from one to four carbon atoms in the alkyl radical, or is an acyclic or cyclic hydrocarbon radical having in each case from one to six carbon atoms, wherein each of the last five radicals mentioned is unsubstituted or is substituted by one or more identical radicals or different from the group consisting of halogen, C1-C4 alkoxy, halo-C1-C4 alkoxy, C2-C4 alkenyl, C2-C alkynyl, C2-C4 alkenyloxy, C2-C4 alkynyloxy, hydroxyl, amino , C 1 -C 4 alkylamino, C 1 -C 4 dialkylamino, nitro, carboxyl, cyano, C 4 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, formyl, carbamoyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl and, in the case of cyclic radicals, also C 1 -C 4 alkyl and halo C 1 -C 4 alkyl, R 8 is C 1 -C 6 alkyl, which is unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, cyano, hydroxyl, C1-C4 alkoxy, C1-C4 alkylthio, CrC4 alkylsulfonyl, C2-C4 alkenyl, C2-C4 alkynyl, phenyl, C3-C9 cycloalkyl, C3-C9 cycloalkoxy , is • Éüiai-a-Hiii • ¿fiUrfUlÉ. a "" - * - - C3-C8 cycloalkyl or C3-C8 cycloalkoxy, wherein the last two mentioned radicals are unsubstituted or substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl and C 1 -C 4 haloalkoxy, R 9, R 10 each, independently of one another, is hydrogen, amino, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkylamino, C 1 -C 4 dialkylamino, C 1 -C 4 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 4 alkoxy, C 3 -C 8 cycloalkoxy or heterocyclyl having from 3 to 6 ring and 1 to 3 ring heteroatoms of the group consisting of oxygen, nitrogen and sulfur, wherein each of the last eight mentioned radicals is unsubstituted or substituted with up to four identical or different radicals from the group consisting of halogen, amino, hydroxyl and, in the case of cyclic radicals, also C 1 -C 4 alkyl, C 4 alkoxy, haloalkyl d and C -.- C4 and halo-C1-C4 alkoxy, or R9 and R10, together with the nitrogen atom that bears them, form a heterocycle having a total of three to six ring atoms and, among these, one to four ring heteroatoms, wherein the other ring heteroatoms which may be present in addition to the nitrogen atom that is present, are selected from the group consisting of oxygen, nitrogen and sulfur, and wherein this heterocycle is unsubstituted or is replaced; R11 is hydrogen, amino, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkyl, C3-C8 cycloalkyl. (C3-C8) cycloalkyl-C1-C4alkyl, C-1-C4alkoxy, (C-? - C4) alkoxy-C1-C4alkoxy, C3-C8cycloalkoxy, C4-C4-alkylcarbonyl, where the last nine radicals The above mentioned are unsubstituted or substituted with one or more identical or different halogen atoms, and in the case of cyclic radicals, also C1-C4 alkyl, C1-C4 alkoxy, halo- C 1 -C 4 alkyl and C 1 -C 4 haloalkoxy, R 14 is hydrogen or C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl, each of which is optionally not substituted with one or more radicals identical or different from the group consists of halogen, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy, and R 15, R 16 each, independently of one another, is hydrogen, phenyl, C 1 -C 4 alkoxy, phenyl C 1 -C 4 alkyl, alkyl of C1-C4, C-1-C4 alkylthio, wherein the last five mentioned radicals are unsubstituted or substituted with one or more identical or different halogen atoms and, in the case of cyclic radicals, also with one or more radicals identical or different from the group consisting of halogen, C 1 -C 4 alkyl and halo C 1 -C 4 alkyl, or R 15 and R16, together with the carbon atom carrying them, form a 3- to 6-membered ring which may contain one or two heteroatoms identical or different from the group consisting of oxygen, nitrogen and sulfur, and which is unsubstituted or substituted with up to four identical or different radicals from the group consisting of halogen, C 1 -C 4 alkyl and halo C 1 -C 4 alkyl.

4. The compound according to any of claims 1 to 3, further characterized in that Aril is phenyl, naphthyl, pyridinyl, pyrimidinyl, furanyl, benzofuranyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, oxadiazolyl, or thienyl, each of the which is not substituted or is substituted with one or more radicals identical or different from the group consisting of halogen, hydroxyl, amino, formyl, C1-C4 alkoxycarbonyl, C4 alkylcarbonyl, C1-C4 alkyl, C2-C4 alkenylc, C2-C4 alkynyl, C1-C4 alkoxy, C1 alkylamino -C4, C 1 -C 4 dialkylamino, aminocarbonyl, C 1 -C 4 alkylaminocarbonyl, C 1 -C 4 dialkylaminocarbonyl, aminosulfonyl, C 1 -C 4 alkylaminosulfonyl, C 1 -C 4 dialkylaminosulfonyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy , C 1 -C 2 haloalkylthio, C 1 -C 2 alkylsulfinyl > alkylsulphonyl of CrC2, haloalkylthio of C -.- C2, haloalkylsulfinyl of CrC2 and haloalkylsulfonyl of C -? - C2; -Y- is a divalent unit of the group consisting of -O-, -S-, -NR11-, -C02-, -SO-, -S02-, -NH-CO-NH-, -O-CO-NH -, -O-NH- and -OCH2CH20- or a trivalent unit of formula -0-N =, m is 0, 1, 2 or 3, n is 1, 2, 3, 4 or 5, R1, R2 each , independently of one another, is a radical of a GJ group comprising C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, hydrogen, C 3 -C 6 cycloalkyl, wherein the said last radical is unsubstituted or substituted with up to four identical or different radicals from the group consisting of halogen and -B-X1, and wherein the first four mentioned radicals of the group G7 are unsubstituted or substituted with one or more radicals identical or different from the group consisting of halogen and -B-X2, wherein X2 is as defined below, or R1 and R2 of a group (CR1R2) form, together with the carbon atom carrying them, a group carbonyl, or two R1 of two groups (CR1R2) directly adjacent is or not directly adjacent, together with the carbon atoms that carry or link them, form a ring of 3, 5 or 6 members that can contain up to two heteroatoms of the group consisting of oxygen, sulfur and nitrogen, and that is not substituted or substituted with up to four identical or different radicals from the group consisting of halogen and -B-X1, or R1 is a point of attachment for the double bond in the case where Y is a trivalent unit = N-0 - which is adjacent to a group CR1R2, and R3, R4 each, independently of one another, is a radical of a group G8 comprising hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci-Cß alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, aryl, arylalkyl of CrC2, arylalkoxy of CrC2, cycloalkyl (C3-Ce) -alkyl of C C2 and cycloalkoxy (C3-10 C8) -alkyl of C1-C4, wherein the cyclic portion of the The last seven mentioned radicals, in each case, is unsubstituted or substituted with up to four identical or different radicals from the group consisting of halogen, nitro, cyano and -B-X1, wherein -B- and X1 are as defined above forward, and where the non-cyclical portion of the last eleven radicals mentioned in Group G8, in each case, is unsubstituted or substituted with one or more radicals identical or different from the group consisting of halogen, nitro, cyano and -B-X2, wherein X2 is as defined below, or R3 and R4 of a group (CR3R4) form, together with the carbon atom carrying them, a carbonyl group, or two R3 of two groups (CR3R4) directly adjacent or 20 not directly adjacent, together with the carbon atoms that carry or link them, form a 3, 5 or 6 member ring that can contain up to two heteroatoms from the group consisting of oxygen, sulfur and nitrogen, and which is not substituted or is replaced with up to four identical radicals or MjMIIIMtagak ^ ak? £ fMtt different from the group consisting of halogen and -B-X1, or R3 is a point of attachment for the double bond in the case where Y is a trivalent unit = N-0- which is adjacent to a group CR3R4, and -B- is a direct bond or a divalent unit of the group consisting of -O-, -S-, -NR11-, -CO- and -C02-; X1 is hydrogen, C1-C4 alkyl. C2-C4 alkenyl) C2-C4 alkynyl or C3-C6 cycloalkyl, the last four mentioned radicals are unsubstituted or substituted with up to five identical or different halogen atoms, X2 is hydrogen or heterocyclyl having from 3 to 6 ring atoms, 1, 2 or 3 of which originate from the group consisting of nitrogen, oxygen and sulfur, and which is unsubstituted or substituted by one or more identical or different halogen atoms, R5 is hydrogen, C -.- C4, halo-C1-C4 alkyl or C3-C6 cycloalkyl, or R3 and R5 of two groups (CR3R4) - or (CR5R6) directly adjacent or not directly adjacent, together with the carbon atoms that the they form a ring of 3, 5 or 6 members which can contain up to two heteroatoms of the group consisting of oxygen, sulfur and nitrogen, and which is unsubstituted or substituted by up to four identical or different radicals from the group consisting of halogen and -B-X1, and R6 is h hydrogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, C 3 -Ce cycloalkyl (C 3 -C 6 cycloalkyl) -C 1 -C 4 alkyl. (C3-C6) -cycloalkoxy-C1-C4 alkyl, C3-C6 cycloalkoxy, (C? -C4) alkoxy-C1-C4 alkyl or halo-C1-C4 alkyl, R7 is hydrogen, amino or C1 alkyl -C4, R8 is C1-C4 alkyl, haloC1-C4 alkyl, C3-C6 cycloalkyl, halo C3-C6 cycloalkyl or (C3-C6) cycloalkyl-C1-C4 alkyl, R9, R10 independently one of another, is hydrogen, amino, formyl or C 1 -C 4 alkyl. or R9 and R10, together with the nitrogen atom carrying them, form a heterocycle having from three to six ring atoms and one to two ring heteroatoms, wherein the other ring heteroatoms which may be present in addition to the atom of nitrogen that is present, are selected from the group consisting of oxygen and nitrogen, R11 is hydrogen, amino, C1-C4 alkylamino, dialkylamino of G1-C4, alkyl of C -.- C4 or cycloalkyl of C3-C6, in where the last five mentioned radicals are unsubstituted or substituted with one or more identical or different halogen atoms, and R 14 is hydrogen or CC alkyl.

5. A process for the preparation of a compound of formula I, or a salt thereof, as claimed in any of claims 1 to 4, comprising: (a) reacting a compound of formula (II) R8 -Fu (II) where Fu is a functional group of the group consisting of ester carboxylic, carboxylic orthoester, carbonyl chloride, carboxamide, carboxylic anhydride and trichloromethyl, with a biguanide of formula (III) or an acid addition salt thereof, 20? N N Aryl (CR1R2) m "Y - (CR3R4) n - CR5 - NR7 - U - N --U - NR R 10 (lll) H aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaah ^^ _ ^^ _ ^ _ B ^ a ^ _ ^^ Mte «. or (b) reacting a compound of formula (IV) wherein Z 1 is an exchangeable radical or a leaving group, for example, chloro, trichloromethyl, C 1 -C 4 alkylsulfonyl and phenyl-C 1 -C 4 alkylsulfonyl or alkyl (CrC 4) phenylsulfonyl, substituted or unsubstituted, with a suitable amine of formula (V) or an acid addition salt thereof, R6 Aryl- (CR1R2) - Y- (CR3R4) n CR5- NHR7 (v) in the formulas (II), (III), (IV) and (V), the radicals R1 to R10, Y and n and m are as defined for the formula (I).

6. A herbicidal or plant growth regulating composition, comprising one or more compounds of formula I, or salts thereof, as claimed in any of claims 1 to 4, if appropriate in a mixture with auxiliaries of formulation.

7. A method for controlling undesirable plants or for regulating the growth of plants, characterized in that it consists in applying to the plants or to the site of the undesirable vegetation, or to the area under cultivation, an effective amount of one or more compounds of formula I, or salts of the lMWMIlUNI > Ma ^ MrfMriMMiri ^ _i ^ MM _ ^ .. ^ MMMHMÉMHt «iiM ^. ^ A > The use of the compounds of the formula I, or the salts thereof, as claimed in any of claims 1 to 4, or of the herbicidal compositions as claimed in claim 6, for controlling undesirable plants or for regulating the growth of the plants. 9. The use according to claim 8, wherein the compounds of formula I, or the salts thereof, are used to control undesirable plants or to regulate the growth of plants in the crops of useful plants. 10. The use according to claim 9, wherein the useful plants are transgenic useful plants. m? tm? t ^^ m