MXPA06007384A - Plant growth regulation - Google Patents

Abstract

The present invention relates to a new class of plant growth regulators. In particular, the invention relates to 5-substituted-1-arylpyrazole-3-carboxylic acid derivative of general formula (I) and a method for treatment of plants with such compounds in order to induce growth regulating responses.

Description

REGULATION OF GROWTH OF PLANTS I DESCRIPTIVE MEMORY The present invention relates to the technical field of agrochemicals and to methods used in agriculture for the regulation of the growth of plants. In particular, the present invention relates to a new class of plant growth regulating agents for the treatment of plants for the purpose of inducing growth regulating responses, which result in superior growth of treated plants, of certain parts of the plants or, more generally, a superior yield of the crops. The term "method for regulating the growth of plants" or the term "growth regulation procedure" or the use of the words "regulation of plant growth" or other terms that use the word "regular", such as used in the present specification, they refer to a variety of plant responses that improve some characteristic of the plant. The "growth regulating agents of plants" are compounds that possess an activity in one or more process (s) for the regulation of the growth of a plant. This type of regulation of plant growth is distinguished from a pesticide action or a reduction in growth, which is sometimes also defined as regulation of the growth of plants, whose intention, however, is to destroy or prevent growth of a plant. For this reason, the compounds used in the practice of this invention are used in amounts that are not phytotoxic with respect to the plant being treated, but which stimulate the growth of the plant or certain parts thereof. Therefore, said compounds can also be referred to as "plant stimulants", and their action can be referred to as "stimulation of plant growth". Regulation of plant growth is a desirable way to improve plants and their harvest in such a way that improved plant growth and better conditions of agricultural practice are obtained compared to untreated plants. This class of molecules can either inhibit or favor cellular activities, often with a lower specificity, compared to that of animal hormones. This means that the plant growth regulating agents identified in plants most often regulate the division, elongation and differentiation of plant cells in such a way that, most often, they have multiple effects on plants. On the molecular basis, plant growth regulating agents may work by affecting membrane properties, controlling gene expression or affecting enzyme activity, or being active in a combination of at least two of the types of interactions that before they have been mentioned. The plant growth regulating agents are chemical products or of natural origin, also called plant hormones (such as non-peptide hormones, for example auxins, gibberellins, cytokinins, ethylene, brassinosteroids or abscisic acid, and salicylic acid), lipooligosaccharides ( for example Nod factors), peptides (for example systemin), fatty acid derivatives (for example jasmonatos), and oligosaccharins (for its compilation see the work: Biochemistry &Molecular Biology of the Plant (2000) [Biochemistry &Molecular Biology of the Plant] (2000), editing coordinators Buchanan, Gruissem, Jones, pages 558-562, and 850-929), or may be products produced by synthesis (such as derivatives of plant growth hormones that occur in the nature, ethephon). Plant growth regulating agents, which work in very small concentrations, can be found in a large number of cells and tissues, but appear to be concentrated in meristems and buds. Next to the selection of the correct compound, it is also important to look for optimal environmental conditions, since several factors that can affect the action of growth hormones are known, such as (a) the concentration of the plant growth regulating agent, properly speaking, (b) the amount applied to the plant, (c) the time of application in relation to the date of flowering, (d) the temperature and humidity before and after the treatment, (e) the moisture content of the plants, and various other . Plant growth regulators may be beneficial for plants, but can sometimes be used to control weeds or to induce defoliation (as do the synthetic auxins 2,4-D and 2,4). , 5-T). The mode of action of the existing regulators of plant growth is not often known. Various goals are discussed and, among these, most of the affected molecules are involved in the regulation of cell division, such as the cell cycle arrest in stage G1 or G2, respectively, others are to signal responses to drought stresses (Biochemistry &; Molecular Biology of the Plant (2000); editing coordinators Buchanan, Gruissem, Jones, pages 558-560). In any case, hormonal control can be identified as an extremely complex cascade of regulations in ascending and descending directions that, for example, can lead to a stimulation of the growth of an organ or a cell type of a plant, but can also lead to a repression in other organs or cell types of the same plant. In many cases, certain kinases are involved either directly or indirectly in the control of plant hormones, and among kinases, protein kinases are primordial and very specific control molecules with respect to cell cycle control. Said kinases are discussed as targets for various plant hormones, as is the case for an auxin and abscisic acid (Biochemistry &Molecular Biology of the Plant (2000); editing coordinators Buchanan, Gruissem, Jones, pages 542-565 and pages 980-985; Morgan (1997), Annu., Rev. Cell. Dev.

Biol., 13, 261-291; Amon et al. (1993), Cell, 74, pages 993-1,007; Dynlacht et al. (1997), Nature, 389, pages 149-152; Hunt and Nasmyth (1997), Curr. Opin. Cell. Biol., 9, pages 765-767; Thomas and Hall (1997), Curr. Opin. Cell. Biol., 9, pages 782-787). The international patent application publication WO 96/33614 already describes the use of an N-arylpyrazole or N-heteroarylpyrazole compound to regulate the growth of plants. In addition, U.S. Pat. with the publication number US 4,810,283 describes the use of N-arylpyrazoles as herbicides. The numbers of patent publications, international WO 87/03781, European EP 0295117, from the USA US 5556873, US 4771066 and international WO 02/066423 describe the repression of insects, arachnids and helminths with 1-arylpyrazoles compounds. In view of the foregoing, it has now been found, surprisingly, that certain derivatives of substituted 1-arylpyrazole-3-carboxylic acids in position 5, and especially certain derivatives of 5-amino-1-arylpyrazole-3-carboxylic acids do not They act mainly as herbicides, but show a superior behavior with respect to their use for the regulation of the growth of plants. The present invention relates to the use of a compound for the regulation of the growth of plants, preferably by application of the compound to plants, to the seeds from which they grow, or to the locus in which they grow, in an amount effective to regulate the growth of the plants, preferably non-phytotoxic, which compound is a substituted 1-arylpyrazole-3-carboxylic acid derivative of the formula (I) or an agriculturally acceptable salt thereof: (I) wherein: R1 is CONR6R7 or CO2R8; W is C-halogen or N; R2 is H or S (O) mR9; R3 is NR10R11, halogen, OH, C?-C6 alkoxy, C2-C6 alkenyl-oxy or C2-C6 alkynyl-OXY; R 4 is H or halogen, preferably H, Cl or Br; R5 is C1-C4 haloalkyl or C1-C4 haloalkoxy, preferably CF3 or OCF3; R6 is H, C? -C6 alkyl, Ci-C? Haloalkyl, C? -C6 alkoxy C? -C6 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, haloalkynyl of C2-C6, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C6-C6 alkyl > C6 alkoxy, CrCe-thio alkyl, (CH2) nR12, (CH2) PR13, C6-C6 alkyl, C6-C6-NR10R11 alkyl or C6-C6-S (O) rR9 alkyl; R7 is H, alkyl of C-I-CT, alkenyl of C3-C6 or alkynyl of C3-C6; or R6 and R7 together with the N atom attached thereto, form a saturated five or six membered ring, which optionally contains an additional ring heteroatom, which is selected from O, S and N, the ring being unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, Ci-Cß alkyl and C -? -C6 haloalkyl; R 8 is H, C 1 -C 6 alkyl, Ci-Cßhaloalkyl, C 2 -C 2 alkenyl, C 2 -C 6 alkynyl or (CH 2) nR 12, preferably H or C 1 -C 4 alkyl or C 1 -C 4 haloalkyl, particularly methyl or ethyl; R9 is C alquilo-C6 alkyl or C?-C6 haloalkyl; R 10 and R 11 are each independently H, C 1 -C 6 alkyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C3-C6 cycloalkyl-C-Cß alkyl, COR14 or CO2R15; or R10 and R11 in common with the N atom attached thereto, form a saturated five or six membered ring, which optionally contains an additional ring heteroatom, which is selected from O, S and N, the ring being unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, Ci-Cß alkyl and C Cß haloalkyl; R12 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, Ci-Cß alkyl, C6 haloalkyl, CrC6 alkoxy, CrC6l haloalkoxy CO2R16, CN, N02, S (O) qR9 , COR16, CONR16R17 and OH; R 13 is heterocyclyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, C 1 -C 4 alkyl, haloC alkyl of CrC 4 >; C1-C4 alkoxy, C1-C4 haloalkoxy, NO2, CN, CO2R16, S (O) qR9, OH and oxo; R14 and R15 are each independently H, CrC6 alkyl, Ci-Cß haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl or Ci-Cß alkyloxy C1 alkyl -C4; R16 and R17 are each independently H, CrC6 alkyl or C? -C6 haloalkyl; m, q and r are, each independently, 0, 1 or 2; n and p are, each independently, 0, 1, 2, 3 or 4; and each heterocyclyl in the aforementioned radicals is independently a heterocyclic radical having from 3 to 7 ring atoms and 1, 2 or 3 heteroatoms in the ring, selected from the group consisting of N, O and S. The invention also encompasses any stereoisomer, enantiomer, geometric isomer or tautomer and mixtures of the compounds of the formula (I) and the respective salts thereof acceptable in agriculture. By the term "acceptable salts in agriculture" are meant salts of the anions or cations which are known and accepted in the specialty for the formation of salts for agricultural use. Suitable salts with bases, for example those formed by compounds of the formula (I) which contain a carboxylic acid group, include alkali metal salts (for example sodium and potassium), alkaline earth metals (for example calcium and magnesium) and of ammonium. Ammonium salts include ammonium salts (NH4 +) and ammonium salts of organic amines, (for example the salts of diethanolamine, triethanolamine, octylamine, morpholine and dioctylmethylamine), and quaternary ammonium salts (NR4 +), example of tetramethylammonium. Suitable salts by addition of acids, for example those formed by compounds of the formula (I) containing an amino group, include salts with inorganic acids, for example hydrochlorides, sulfates, phosphates and nitrates, and salts with organic acids, for example acid acetic. In the present patent specification, including the appended claims, the aforementioned substituents have the following meanings: Halogen means fluorine, chlorine, bromine or iodine.

The term "halo", before the name of a radical, means that this radical is partially or completely halogenated, that is, substituted with F, Cl, Br or I, in any combination. The term "CI-CT alkyl" means a saturated, non-cyclic, unbranched or branched hydrocarbyl radical having 1, 2, 3, 4, 5 or 6 carbon atoms (indicated by a range of C atoms within the parentheses), such as, for example, a methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tere-butyl radical. The same applies to alkyl groups in compound radicals such as "alkoxyalkyl". The alkyl radicals, and also in compound groups, unless otherwise defined, preferably have from 1 to 4 carbon atoms. "Haloalkyl of C? -C6" means an alkyl group mentioned within the term "Ci-Ce alkyl" in which one or more hydrogen atoms are replaced by the same number of halogen atoms, identical or different, such as monohaloalkyl , perhaloalkyl, CF3, CHF2, CH2F, CHFCH3) CF3CH2, CF3CF2 > CHF2CF2, CH2FCHCI, CH2CI, CCI3l CHCI2 or CH2CH2CI. "Alkoxy of C-t-Cß-C-C6 alkyl" means a C6-C6 alkyl which is substituted with a C6-C-alkoxy. "D-Cβ alkoxy" means an alkoxy group, which carbon chain has the meaning given within the term "CrC6 alkyl".

"Haloalkoxy" is, for example, OCF3, OCHF2, OCH2F, CF3CF2O, OCH2CF3 or OCH2CH2CI. "C2-Ce alkenyl" means a non-cyclic carbon chain, unbranched or branched, having a number of carbon atoms corresponding to this designated range and containing at least one double bond which may be located at any position of the respective unsaturated radical. "C2-Ce alkenyl" refers, for example, to the group vinyl, allyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentenyl or hexenyl. "C2-C6 alkynyl" means a non-cyclic carbon chain, unbranched or branched, having a number of carbon atoms corresponding to this designated range and containing a triple bond that may be located at any position of the respective radical unsaturated "Alkynyl of C2-Ce" refers, for example, to the group propargyl, 1-methyl-2-propynyl, 2-butynyl or 3-butynyl. "C3-C6 cycloalkyl" designates monocyclic alkyl radicals, such as the cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl radical. "Cycloalkyl of Cs-Cβ-C- [alpha] -C6 alkyl" means a C-C [beta] alkyl group which is substituted with a C3-C8 cycloalkyl group. "C 1 -C 2 -NC alkyl" means an alkyl group of C Cß which is substituted with a CN group, for example cyanoethyl. "Alkyl of C? -C6-S (0) rR9" means an alkyl group of C? -C6 which is substituted with a group S (O) rR9, for example methylthiomethyl.

A "heterocyclyl" group can be saturated, unsaturated or heteroaromatic; preferably contains one or more, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably selected from the group consisting of N, O and S; it is preferably an aliphatic heterocyclic radical having from 3 to 7 ring atoms or a heteroaromatic radical having from 5 to 7 ring atoms. The heterocyclic radical can be, for example, a heteroaromatic radical or ring (heteroaryl) such as, for example, a mono-, bi- or polycyclic aromatic system, in which at least 1 ring contains one or more heteroatoms, for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, furyl, pyrrolyl, pyrazolyl, midazolyl and triazolyl, or is a partially or totally hydrogenated radical such as oxiranyl, oxetanyl, oxolanyl (= tetrahydrofuryl) , oxanyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl and morpholinyl. The expression "one or more radicals selected from the set consisting of" in the definition is to be understood as meaning in each case one or more identical or different radicals, selected from the designated set of radicals, unless specific limitations are expressly defined. The compounds of the formula (I) indicated, according to the invention, or their salts, in which individual radicals have one of the preferred meanings which have already been pointed out or which are pointed out below and particularly those shown in the examples of the Tables, or in particular those in which two or more of the preferred meanings which have already been pointed out or which are indicated below, are of particular interest, mainly because of the more potent herbicidal action, the better selectivity and the greatest facility for preparation. Of particular interest are compounds of the formula (I), in which a radical selected from the group of radicals R1, R2, R3, R4, R5 and W is preferably defined as follows, in which the definition of the radical is independent of the definitions of the other radicals of said set. Preferred compounds of the formula (I) contain a combination of radicals from said set, which comprise two or more preferred meanings set forth below. In the following preferred definitions it is generally understood that, when certain symbols are not specifically defined, they must be as defined above in the specification. Preferably R is CONR6R7. Preferably W is C-CI or C-Br (more preferably W is C-Cl). Preferably R2 is S (O) mR9, wherein R9 is C1-C3 alkyl or C1-C3 haloalkyl (more preferably R9 is CF3). Preferably R3 is NR10R11, halogen, OH or C? -C3 alkoxy. Preferably R4 is Cl or Br (more preferably R4 is Cl).Preferably R5 is CF3 or OCF3. Preferably R6 is H, C1-C4 alkyl, C1-C4 haloalkyl, C3 alkyl alkoxy-C1-C3 alkyl, C3-C4 alkenyl, C3-C4 haloalkenyl, C3-C4 alkynyl, C3-haloalkynyl C4, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C3 alkyl) Cs alkoxy, CrC3-thio alkyl, (CH2) nR12, (CH2) PR13, C6-C6 alkyl, C-alkyl ? -C6-NR10R11 or C6-C6-S (O) rR9 alkyl. Preferably R7 is H, C 1 -C 4 alkyl, C 3 -C 4 alkenyl or C 3 -C 4 alkynyl; or preferably Rd and R7 in common with the N atom attached thereto, form a saturated five- or six-membered ring, which optionally contains an additional ring heteroatom, which is selected from O, S and N, the ring being replacing or substituted with one or more radicals selected from the group consisting of halogen, C1-C3 alkyl and C1-C3 haloalkyl. Preferably R10 and R11 are each independently H, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 alkenyl, C3-C4 haloalkenyl, C3-C4 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C3 alkyl, COR14 or C02R15; or Preferably R10 and R11 in common with the N atom attached thereto, form a saturated five or six membered ring, optionally containing an additional ring heteroatom, selected from O, S and N, the ring being replacing or substituted with one or more radicals selected from the group consisting of halogen, C1-C3 alkyl and C1-C3 haloalkyl. Preferably R12 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, C3 alkyl, C1-C3 haloalkyl, C3 alkoxy, C1-C3 haloalkoxy, CO2R16, CN, N02, S (O) qR9, COR16, CONR16R17, NR16R17 and OH. Preferably R13 is heterocyclyl unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, C1-C3 alkyl, haloalkyl of C ^ Cs, C1-C3 alkoxy, C3 haloalkoxy, NO2, CN, CO2R16 , S (O) qR9, OH and oxo. Preferably R 14 and R 15 are each independently H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 3 alkenyl, C 2 -C 3 haloalkenyl or C 2 -C 3 alkynyl, particularly C 1 -C 4 alkyl . Preferably R 16 and R 17 are each independently H, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl. Preferably, each heterocyclyl in the aforementioned radicals is independently a heterocyclic radical having from 3 to 6 ring atoms and 1, 2 or 3 heteroatoms in the ring, selected in the set consisting of N, O and S. A preferred class of compounds of the formula (I) for use as growth regulating agents of the plants in the invention, is that of those in which: R1 is CONR6R7; W is C-CI or C-Br (more preferably W is C-CI); R2 is S (0) mR9; R3 is NR10R11, halogen, OH, C1-C3 alkoxy, C2-C6 alkenyl-oxy or C2-Cs-oxy alkynyl; R4 is Cl or Br (more preferably R4 is Cl); R5 is CF3 or OCF3; R6 is H, C1-C4 alkyl, C4 haloalkyl, C1-C3 alkoxy-C1-C3 alkyl, C3-C4 alkenyl, C3-C4 haloalkenyl, C3-C4 alkynyl, C3-C4 haloalkynyl , C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C3 alkyl, C1-C3 alkoxy, C3-alkylthio, (CH2) nR12 or (CH2) PR13; R7 is H, C1-C4 alkyl, C3-C4 alkenyl or C3-C4 alkynyl; or preferably R6 and R7 in common with the N atom attached thereto, form a saturated five- or six-membered ring, which optionally contains an additional ring heteroatom, which is selected from O, S and N, the ring being replacing or substituted with one or more radicals selected from the group consisting of halogen, C3 alkyl, and C1-C3 haloalkyl; R9 is C1-C3 alkyl or C1-C3 haloalkyl (more preferably R9 is CF3; R10 and R11 are each independently H, Ct-C3 alkyl, C3-C3 haloalkyl) C3- alkenyl C4l C3-C4 haloalkenyl, C3-C4 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C3 alkyl, COR14 or CO2R15; or R10 and R11 in common with the N atom attached thereto, form a saturated five or six membered ring, which optionally contains an additional ring heteroatom, which is selected from O, S and N, the ring being replacing or substituted with one or more radicals selected from the group consisting of halogen, C1-C3 alkyl and C1-C3 haloalkyl; R12 is phenyl unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, CO2R16, CN, NO2 , S (O) qR9, COR16, CONR16R17, NR16R17 and OH; R13 is heterocyclyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, NO2) CN, CO2R16 , S (O) qR9, OH and oxo; R14 and R15 are each independently H, C1-C3 alkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl or Ci-C3-alkyl alkoxy of C1-C4; R 16 and R 17 are each independently H, C 1 -C 3 alkyl or C C 3 haloalkyl; and each heterocyclyl in the aforementioned radicals is independently a heterocyclic radical having from 3 to 6 ring atoms and 1, 2 or 3 heteroatoms in the ring, selected from the group consisting of N, O and S. A further preferred class of compounds of the formula (I) for use as growth regulating agents of the plants in the invention, is those in which: R1 is CONR6R7; W is C-CI; R2 is H, or S (0) mR9; R3 is NR10R11, halogen, OH or C? -C3 alkoxy; R4 is CI; R5 is CF3; R 6 is H, C 1 -C 4 alkyl, C 1 -C 3 alkoxy C 1 -C 2 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-alkyl of C C2, C3 alkyl alkoxy C3 alkylthio; (CH2) nR12 or (CH2) PR13; R7 is H, C1-C3 alkyl, C3-C4 alkenyl or C3-C4 alkynyl; R9 is methyl or CF3; R10 and R11 are each independently H, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 alkenyl, C3-C4 haloalkenyl, C3-C4 alkynyl, C3-C6 cycloalkyl, cycloalkyl of C3-C6-C1-C3 alkyl, COR14 or CO2R15; or R12 is phenyl unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, C1-C3 alkyl, C3 haloalkyl, CrC3l alkoxy CO2R16, CN and NO2, R13 is unsubstituted or substituted heterocyclyl one or more radicals selected from the group consisting of halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, NO2, CN, CO2R16, S (O) qR9, OH and oxo; R 14 and R 15 are each independently C 1 -C 3 alkyl; R 16 and R 17 are each independently H or C 1 -C 3 alkyl; and each heterocyclyl in the aforementioned radicals is independently a heterocyclic radical having from 3 to 6 ring atoms and 1, 2 or 3 heteroatoms in the ring, selected from the group consisting of N, O and S. A further preferred class of compounds for use as plant growth regulating agents in the invention is that of those of the formula (la), as depicted below, wherein: R1 is CONR6R7; W is C-CI; R2 is H, or S (O) mR9; R3 is NHR10; R4es CI; R5 is CF3; R6 is H, C1-C5 alkyl, d-C2 alkoxy C1-C2 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C alkyl? -C2, furfuryl or tetrahydrofurfuryl; R7 is H or C1-C3 alkyl, R9 is methyl, ethyl or CF3; R10 is H, methyl or ethyl. A further preferred class of compounds for use as plant growth regulating agents in the invention is that of the formula (Ib), as represented below, wherein: R1 is CO2R8; W is C-CI; R2 is H, or S (O) mR9; R3 is NR10R11; R4 is CI; R5 is CF3; R8 is H, methyl or ethyl. R9 is methyl, ethyl or CF3; R10 is H, methyl or ethyl; and R11 is H. A further preferred class of compounds for use as growth regulating agents of plants in the invention is that of the formula (le), as represented below, in that: R1 is CONR6R7; W is C-CI; R2 is S (O) mCF3; R3 is NR10R11, halogen, OH or C2C2 alkyl; R4 is Cl; R5 is CF3; R6 is H or C? -C3-thio alkyl; R7 is H; R > 110U is C1-C3 alkyl, COR 1144 or CO2R > 1'5 °; R11, R14 and R15 are each independently C1-C3 alkyl. Some of the compounds of the formula (I) are not known in the prior art. Therefore, a further feature of the invention relates to these new compounds of the formula (I) Therefore, according to a further feature of the invention, a substituted 1-arylpyrazole-3-carboxylic acid derivative is provided in position 5 of formula (I), or a salt thereof as defined in formula (I).

O) wherein: i) R1 is C02R8; R2 is H or S (0) mR9; R3, R4, R5, W and m are as defined above; R8 is H; and R9 is C2-Cß alkyl or C-i-Cß haloalkyl; or ii) R1 is CONR6R7; R6 is Ci-Cß alkyl, CrC6 haloalkyl, C?-C6 alkoxy-C1-C6 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C alqu alkynyl, C2-C6 haloalkynyl, cycloalkyl of C3-C7, C3-C7 cycloalkyl-d-C-alkyl, C6-C6 alkoxy, C6-C6-alkyl, (CH2) nR12, (CH2) PR13, C6-C6-alkyl, alkyl of C? -C6-NR10R11 or C6-C6-S (O) rR9 alkyl; or R6 and R7 in common with the N atom attached thereto, form a saturated five or six membered ring, which optionally contains an additional ring heteroatom, which is selected from O, S and N, the ring being replacing or substituted with one or more radicals selected from the group consisting of halogen, CI-CT alkyl, and C-α-C6 haloalkyl; and R 2, R 3, R 4, R 5, R 7, R 9, R 10, R 11, R 12, R 13, W, n, p and r are as defined in formula (I); with the exclusion of the compound in which: R1 is CON (CH3) 2; R2 is CF3S; R3 is OH; R4 is Cl, R5 is CF3; and W is C-CI. The above compound is specifically excluded since it is known, however, its use as a plant growth regulating agent has not yet been reported. The compounds of formula (I) above can be prepared by the application or adaptation of known methods (ie methods used previously or described in the literature). In the following description when symbols that appear in the formulas are not specifically defined, it is to be understood that these are as "previously defined" according to the first definition of each symbol in the specification. It is to be understood that in the descriptions of the following procedures, the sequences can be performed in different orders, and that appropriate protecting groups may be required to achieve the desired compounds. Compounds of the formula (I) above can be prepared by the application or adaptation of known methods (ie methods used previously or described in the literature). In the following description, when symbols that appear in the formulas are not specifically defined, it is to be understood that these are as "have been previously defined" according to the first definition of each symbol in the specification.

It is to be understood that in the descriptions of the following procedures, the sequences can be performed in different orders, and that appropriate protecting groups may be required to achieve the desired compounds. According to a feature of the invention, compounds of the formula (I) wherein R1 is C02H, R2 is H or S (O) mR9, R9 is C2-C6 alkyl or Ci-Cß haloalkyl, and the others Radicals are as defined above, can be prepared by the reaction of a corresponding compound of the formula (II): wherein R2, R3, R4, R5 and W are as defined above, using an aqueous sulfuric acid, generally a 40% sulfuric acid up to 60%, at a temperature between 80 ° C and 170 ° C, preferably from 120 ° C to 150 ° C. According to a further feature of the invention, compounds of the formula (I) wherein R1 is CO2H, R2 is H, R3 is NHR11, and the other radicals are as defined above, can be prepared by the reaction of a corresponding compound of the formula (II) above, wherein R2 is R9SO or R9SO2 (preferably CF3SO or CF3SO2), using an aqueous sulfuric acid, generally a 40% sulfuric acid up to 60%, at a temperature between 80 ° C and 170 ° C, preferably from 120 ° C to 150 ° C. According to a further feature of the invention, compounds of the formula (I) wherein R1 is CONR6R7; R6 is d-C6 alkyl, d-C6 haloalkyl, C-? - C6 alkoxy C? -C6 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2 haloalkynyl -C6, C3-C7 cycloalkyl, C3-C7 cycloalkyl-d-C-alkyl, d-C-alkoxy, (CH2) nR12, (CH2) PR13, d-C6-alkyl, d-C6 alkyl -NR10R11 or d-C6-S (O) rR9 alkyl; R7 is as previously defined; or R6 and R7 in common with the N atom attached to them, form a saturated five or six membered ring, which optionally contains an additional ring heteroatom, which is selected from O, S and N, the ring being unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, C1-C6 alkyl and haloalkyl of d-C6; and the other radicals are as defined above, can be prepared by the reaction of a corresponding compound of the formula (I) in which R1 is CO2H, with N.N'-carbonyldiimidazole to give the corresponding imidazolide of the formula III : followed by the reaction, preferably in situ, with an amine of the formula (IV): HNR6R7 (IV) wherein R6 and R7 are as defined above. The reaction is generally carried out in a solvent such as tetrahydrofuran or dioxane, at a temperature comprised between 20 ° C and 100 ° C, preferably between 30 ° C and 70 ° C. According to a further feature of the invention, compounds of the formula (I) in which R3 is NR10R11, in which at least one of the R10 and R11 is not H, and the other radicals are as defined above, can be prepared by alkylation or acylation of the corresponding compound of the formula (I), wherein R3 is NH2, using an alkylating or acylating agent of the formula (V) or (VI): R10-L (V) R11-L (VI) wherein R10 and R1 are as defined above, with the exclusion of H, and L and Li are, each of them, a leaving group.

The alkylations, when R 10 and / or R 11 are each Ci-Cß alkyl, d-Cß haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl or C3-C6 cycloalkyl-CrC6 alkyl, and L and L? are each, preferably halogen, alkylsulfonyloxy or arylsulfonyloxy (more preferably chlorine, bromine, iodine, methylsulfonyloxy or p-toluenesulfonyloxy) are generally carried out in the presence of a base, in an inert solvent such as tetrahydrofuran , dioxane, acetonitrile, toluene, diethyl ether, dichloromethane, dimethylsulfoxide or N, N-dimethylformamide, at a temperature between -30 ° C and 200 ° C, preferably at 20 ° C to 100 ° C. The base is generally an alkali metal hydroxide such as potassium hydroxide, an alkali metal hydride such as sodium hydride, an alkali metal carbonate such as potassium carbonate or sodium carbonate, an alkali metal alkoxide such as sodium methoxide, an alkaline earth metal carbonate such as calcium carbonate, or an organic base such as a tertiary amine, for example triethylamine or ethyldiisopropylamine, or pyridine, or 1,8-diaza-bicyclo [5.4.0] undec-7-ene (DBU). The acylations, when R10 and / or R11 are each COR14 or CO2R15, and L and L1 are each preferably chlorine or bromine (more preferably chlorine), are optionally carried out in the presence of a base . The bases, solvents and temperatures that can be used are similar to those used for alkylations.

By performing sequential reactions of alkylation or acylation, compounds of the formula (I) in which R 3 is NR 10 R 11 can be prepared in which R 10 and R 11 have different meanings. According to a further feature of the invention, compounds of the formula (I) in which R1 is CONR6R7, R2 is S (O) mR9, R3 is d-Cß alkoxy, R6 is C6-C6 alkyl thio , and the other radicals are as defined above, can be prepared by the reaction of a corresponding compound of the formula (I) in which R1 is CONHR7, with a compound of the formula (VII): R6-L2 (VII) ) wherein R6 is d-C6-alkyl and L2 is a leaving group, generally halogen and preferably Cl. According to a further feature of the present invention, compounds in which m is 1 or 2, and other radicals are as defined above, they can be prepared by oxidizing a corresponding compound in which m is 0 or 1. Oxidation is generally carried out using an oxidizing agent such as m-chloroperbenzoic acid or sodium periodate in a solvent inert, for example methylene chloride, at a temperature from -40 ° C to the ref temperature luxury of the solvent. Compounds of the formula (I) in which R1 is CONH2, can be prepared from the corresponding compounds in which R1 is CN, according to known methods, for example by reaction with a concentrated sulfuric acid at a temperature of 50. ° C to 150 ° C.

Intermediates of the formula (II) in which R3 is NR10R11 or halogen, can be prepared according to methods described in Patent Publication Nos. WO 87/03781, EP 295117 and US 5232940. Intermediates of the Formula (II) in which R3 is Ci-Cß alkoxy, can be prepared according to methods described in Patent Publication Nos. EP 035809 and US 5047550. Intermediates of the formula (II) wherein R3 is OH, can be prepared according to methods described in Patent Publication No. WO 01/40195. The compounds of the formula (III) are new and as such constitute a further feature of the invention and can be prepared as described above. The compounds of the formulas (II), (IV), (V), (VI) and (Vil) are known or can be prepared according to known methods. A collection of compounds of the formula (I), which can be synthesized according to the aforementioned procedures, can be further prepared in a parallel manner, which can be carried out manually, partially automatically or fully automatically. In this context, it is possible to automate the process of the reaction, the treatment or the purification of the products or of the intermediates. In total, it is to be understood that this means a process as described, for example, by S.H. DeWitt in "Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated Synthesis" [Annual Reports on Combinatorial Chemistry and Molecular Diversity: Automatic Synthesis], Volume 1, published by Escom., 1997, pages 69 to 77. To carry out the reaction and the treatment in a parallel manner, a series of commercially available equipment may be used, such as are available, for example, from Stem Corporation, Woodrolfe Road, Tollesbury, Essex, CM9 8SE England, or from Radleys Discovery Technologies, Saffron Walden, Essex, CB11 3AZ, England. To carry out the parallel purification of compounds (I), or intermediate compounds obtained during the preparation, there are available, among others, chromatography equipment, for example those from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504 , USA The mentioned equipment makes possible a modular procedure, in which the individual steps of the process are automatic, but between the steps manual operations must nevertheless be carried out. This can be avoided by using partially or fully integrated automation systems, in which the automation modules in question are manipulated, for example, by means of robots or robots. Such automation systems can be purchased for example from Zymark Corporation, Zymark Center, Hopkinton, MA 01748, USA. In addition to the methods described above, the compounds of the formula (I) can be prepared by methods that are fully or partially supported in solid phases. For this purpose, individual intermediates, or all intermediates of the synthesis or of a synthesis adapted to accommodate the process in question, are made in a manner fixed to a synthetic resin. Methods of synthesis that are supported by solid phases have been described extensively in the specialized literature, for example in the citation of: Barry A. Bunin in "The Combinatorial Index", published by Academy Press, 1998. The use of synthesis methods, which are supported by solid phases, allows a series of protocols that are known from the bibliography that, in turn, can be performed in a manual or automatic way. For example, the "tea bag method" (by Houghten, see U.S. Patent 4,631,211).; and the appointment of Houghten et al., Proc. Nati Acad. Sci., 1985, 82, 5,131-5,135) can be partially automated with IRORI products, 11149 North Torrey Pines Road, La Jolla, CA 92037, USA. Parallel syntheses, which are supported by solid phases, can be successfully automated, for example using equipment from Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, CA 94070, USA or from MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Germany. The preparation according to the procedures described herein provides compounds of the formula (I) in the form of collections of substances or libraries of substances. Subject matter of the present invention are therefore also libraries of the compounds of the formula (I) which contain at least two compounds of the formula (I), and of their precursors. The following non-limiting Examples illustrate the preparation of the compounds of the formula (I).

A. CHEMICAL EXAMPLES In the Examples that follow, the amounts (and also the percentages) are based on the weight, unless otherwise stated. The relationships between solvents are based on volumes.

EXAMPLE 1 5-Amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -4-trifluoromethylthio-1H-pyrazole-3-carboxylic acid (compound 2.10) A stirred mixture of 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -4-trifluoromethylthio-1H-pyrazole-3-carbonitrile (35.5 g, 84.3 mmole) and sulfuric acid (50% strength) , 600 ml) was heated at 135 ° C for 7 hours. The cooled mixture was added to a mixture of ice and water, and the precipitate was filtered off, washed with water and dried in air. Trituration with tetrachloromethane gave the title compound as off-white crystals (30.6 g, 82% yield), m.p. 199 ° C. 1 H NMR (DMSO-d 6): 6.66 (broad s, 2H, NH 2), 8.23 (s, 2H, Ar-H), and 13.03 (broad s, 1H, COOH).

EXAMPLE 2 Amide of 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -4-trifluoromethylthio-1H-pyrazole-3-carboxylic acid (compound 1.4) A mixture of 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -4-trifluoromethylthio-1H-pyrazole-3-carboxylic acid (1.00 g, 2.27 mmol) and 1,1-dicarbonylimidazole (0.45) g, 2.72 mmol) in dioxane was heated at 50 ° C for 2 hours. Then an aqueous ammonia solution (33%, 80 ml) was added and stirring was continued at 50 ° C for 4 hours. The cooled mixture was diluted with water and extracted with a mixture of ethyl acetate and heptane (1: 1) The combined organic phase was washed with aqueous potassium hydrogensulfate (5%), dried over magnesium sulfate and evaporated to give the title compound (0.980 g, 98% yield) as a white foam.1H NMR (CDCl3): 4.36 (broad s, 2H, NH2), 5.60 and 6.69 (broad s, 2H, C ( O) NH2), and 7.82 (s, 2H, Ar-H).

EXAMPLE 3 5-Amino-1- (2,6-dichloro-4-trifluoromethyl-phenyl-phenyl-4-trifluoromethyl-1H-pyrazole-3-carboxylic acid cyclopropylamide (compound 1.1) A mixture of 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -4-trifluoromethylthio-1H-pyrazole-3-carboxylic acid (0.85 g, 1.83 mmol) and 1,1-dicarbonylimidazole (0.36 g) , 2.20 mmoles) in dioxane was heated at 55 ° C for 2 hours. Cyclopropylamine (0.20 ml, 2.83 mmol) was then added and stirring was continued at 55 ° C for 6 hours. The cooled mixture was diluted with water, extracted with ethyl acetate, washed with an aqueous solution of potassium hydrogensulfate (5%), dried over magnesium sulfate and evaporated to give the title compound (0.762 g, 87% yield) as whitish crystals, mp 193 ° C. 1 H NMR (CDCl 3): 0.64 (m, 2H, cyclopropyl), 0.83 (m, 2H, cyclopropyl), 2.87 (m, 1 H, cyclopropyl), 4.31 (broad s, 2H, NH 2), 6.82 (broad s, 1 H, C (O) NH), and 7.80 (s, 2H, Ar-H).

EXAMPLE 4 Proparmylamide of 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -4- trifluoromethylsulfinyl-1 H -pyrazole-3-carboxylic acid (compound 1134) To a suspension of 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -4-trifluoromethylthio-1 H -pyrazole-3-carboxylic acid propargyl amide (0.71 g, 1.43 mmol) in dichloromethane was added to the suspension. slowly added a solution of m-chloroperbenzoic acid (70%, 0.41 g, 1.68 mmol) in dichloromethane. After stirring for 17 hours at 20 ° C, an aqueous solution of sodium sulfite and sodium hydrogencarbonate (5%: 5%) was added., 25 ml) and stirring was continued for 15 minutes. The aqueous phase was extracted with dichloromethane, dried over magnesium sulfate, evaporated and purified by flash chromatography (in the presence of silica, with a mixture of heptane and ethyl acetate) to give the title compound (0.604 g. , yield 86%) in the form of white crystals, mp 207 ° C. 1 H NMR (CDCl 3): 2.28 (t, 1 H, propargyl), 4.20 (m, 2H, propargyl), 5.17 (broad s, 2H, NH 2), 6.88 (broad t, 1H, C (O) NH), and 7.83 (s, 2H, Ar-H).

EXAMPLE 5 5-Amino-1- (2, β-dichloro-4-trifluoromethyl-phenyl) -4-trifluoromethylsulfonyl-1H-pyrazole-3-carboxylic acid amide (compound 1.268) A stirred mixture of 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -4-trifluoromethylsulfonyl-1-pyrazol-3-carbonitrile (1.06 g, 2.21 mmol) and concentrated sulfuric acid (1 mi) was heated at 100 ° C for 3 hours. The cooled mixture was added to a mixture of ice and water and the precipitate was filtered off, washed with water and dried in air. Purification by flash chromatography (in the presence of silica, with chloroform) gave the title compound (0.869 g, 83% yield) as off-white crystals, m.p. 217 ° C. 1 H NMR (DMSO-d 6): 7.39 (broad s, 2H, NH 2), 7.57 and 7.78 (broad s, 2H, C (O) NH 2 and 8.25 s, 2H, Ar-H).

EXAMPLE 6 5-Amino-1- (2,6-dichloro-4-trifluoromethyl-phenyl) -1-t-pyrazole-2-carboxylic acid (compound 2.1) A stirred mixture of 5-amino-1- (2,6-dichloro-4-trifluoromethylene) -4-trifluoromethylsulfinyl-1H-pyrrazol-3-carbonitrile (5.00 g, 11.4 mmol) and sulfuric acid (50%, 100 ml) was heated at 135 ° C for 3 hours. The cooled mixture was added to a mixture of ice and water, and the pH was adjusted to 4 by the addition of aqueous sodium hydroxide (6 N, approximately 230 ml), and then extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, evaporated to dryness and purified by flash chromatography (in the presence of silica, with a mixture of chloroform and ethanol) with subsequent trituration with tetrachloromethane to give the title compound (3.00 g). , yield 77%) in the form of whitish crystals, mp 213 ° C. 1 H NMR (DMSO-d 6): 5.69 (broad s, 2 H, NH 2), 5.76 (s, 1 H, pyrazole-H) and 8.20 (s, 2 H, Ar-H).

EXAMPLE 7 1- (2,6-Dichloro-4-trifluoromethyl-phenyl) -5-ethoxy-4-trifluoromethylthio-1H-pyrazole-3-carboxylic acid amide (compound 3.3) a) To a stirred suspension of sodium hydride (0.41 g, at 60 %, 10.3 mmole) in dioxane (150 ml) was added a solution of 1- (2,6-dichloro-4-trifluoromethylphenol) -5-hydroxy-4-trifluoromethylthio-1H-pyrazole-3-carbonitrile. (4.00 g, 8.53 mmol) in dioxane (50 ml). After the evolution of gases had ceased, the mixture was heated to reflux and diethyl sulfate (1.25 ml, 9.47 mmol) was added, and then heated to reflux for 6 hours. The cooled mixture was acidified with an aqueous solution of potassium hydrogensulfate (5%), extracted with dichloromethane, and the organic phase was dried over magnesium sulfate and evaporated. The resulting gum was triturated with pentane to give 1- (2,6-dichloro-4-trifluoromethylphenyl) -5-ethoxy-4-trifluoromethylthio-1H-pyrazole-carbonitrile (2.68 g, 70% yield) as crystals whitish, pf 106 ° C. 1 H NMR (CDCl 3): 1.36 (t, 3 H, CH 3), 4.71 (q, 2 H, OCH 2) and 7.76 (s, 2 H, Ar-H). b) A stirred mixture of 1- (2,6-dichloro-4-trifluoromethylphenyl) -5-ethoxy-4-trifluoromethylthio-1H-pyrazole-3-carbonitrile (0.55 g, 1.22 mmol) and concentrated sulfuric acid (0.55 ml) ) was heated at 100 ° C for 3 hours. The cooled mixture was added to a mixture of ice and water and the precipitate was filtered off, washed with water and dried in air. The crude product was dissolved in a mixture of heptanes and ethyl acetate (1: 1) and filtered. The filtrate was evaporated to give the title compound (0.42 g, 73% yield) as yellowish crystals, m.p. 161 ° C. 1 H NMR (CDCl 3): 1.32 (t, 3 H, CH 3), 4.68 (q, 2 H, OCH 2), 5.54 and 6.69 (broad s, 2 H, C (0) NH 2) and 7.77 (s, 2 H, Ar-H) . The following preferred compounds of the formulas (la), (Ib) and (le), shown in Tables 1 to 3 also form part of the present invention and are obtained by, or in a manner analogous to, the foregoing Examples 1 to 7, or the general methods described above. The following abbreviations are used in Tables 1 to 3. "Cpd" means Compound Number. The numbers of compounds are given only for reference purposes. RF means the retention time determined from a thin layer chromatography on silica gel, using ethyl acetate as eluent.

TABLE 1 Compounds of the formula (la) TABLE 2 Compounds of the formula (Ib) flb) TABLE 3 Compounds of the formula (le) Another aspect of the invention is a method for regulating the growth of plants whose plants are monocotyledonous or dicotyledonous cultivated plants, preferably selected from among the set of economically important field grown plants such as, for example, wheat, barley, rye, triticale , rice, corn, sugar beet, cotton or soybean, particularly corn, wheat and soybeans as well as vegetables and ornamental plants, said method comprising applying to said plants, the seeds from which they grow or the locus in which they grow. they grow, a non-phytotoxic amount, effective to regulate the growth of the plants, of one or more compounds of the formula (I). A further aspect of the invention is a method for regulating the growth of plants, which plants are monocotyledonous or dicotyledonous cultivated plants, preferably selected from among the set of economically important field grown plants, for example, wheat, barley, rye , triticale, rice, corn, sugar beet, cotton or soybean, particularly corn, wheat and soybeans, as well as vegetables and ornamental plants, said method comprising applying to said plants, the seeds from which they grow or the locus in that they grow, a non-phytotoxic amount, effective to regulate the growth of the plants, of a compound having the formula (I) in a mixture with support materials and / or surfactants. A further aspect of the invention is a method for regulating the growth of plants, whose plants are monocotyledonous or dicotyledonous cultivated plants, preferably selected from among the set of economically important field grown plants, such as, for example, wheat, barley, rye, triticale, rice, corn, sugar beet, cotton or soy, particularly corn, wheat and soybeans, as well as vegetables and ornamental plants, said method comprising applying to said plants, the seeds from which they grow or at the locus in which they grow, a non-phytotoxic amount, effective to regulate the growth of the plants, of a compound having the formula (I) together with an additional active compound, selected from the group consisting of acaricides, fungicides, herbicides, insecticides, nematicides or plant growth regulating substances, which are not identical to the defi nested by the formula (I). In the case where the compound having the formula (I) is to be applied, either alone or together with another additional active compound, directly to the seeds, there are various ways of how to develop said treatment of the seeds, such as by "coating with films = in English filmcoating" which is characterized by the creation of a liquid formulation containing an applicable polymer that will be applied to the seeds, improving with this the adhesion, the covering and the distribution of the compounds on the seeds. Among the additional active compounds to be applied together with a compound having the formula (I), either applied as an additional active compound or applied in a combination of several additional active compounds, the following compounds are specifically mentioned as examples of said additional active compounds: 2-phenylphenol, 8-hydroxyquinoline sulfate; acibenzolar-S-methyl; actinovate; aldimorf; amidoflumet; ampropilfos; ampropylphos-potassium, andoprima; Anilazine; azaconazole; azoxyestrobin; benalaxyl; benodanil; benomyl, benthiavalicarb-isopropyl; benzamacrilo, benzamacriloisobutilo; bilanafos; binapacryl; biphenyl; bitertanol; blasticidin-S; boscalida; bromuconazole; bupirimate; butiobate; Butylamine; calcium polysulfide; capsymycin; captafol; they catch carbendazim; carboxy; carpropamide; carvona; quinomethionate; clobentiazone; chlorphenazole; chloroneb; Chlorothalonil; clozolinate; cis-1- (4-chlorophenyl) -2- (1 H-1, 2,4-triazol-1-yl) -cycloheptanol; clozilacona; Ciazofamide; ciflufenamide; cymoxanil; ciproconazole; cyprodinil; ciprofuram; dagger G; debacarb; diclofluanide; diclone; dichlorophene; diclocimet; diclomezine; diclorane; dietofencarb; difenoconazole; diflumetorim; dimetirimol; dimetomorf; dimoxiestrobin; diniconazole; diniconazole-M; dinocap; diphenylamine; dipyritiona; ditalimfos; dithianone; Dodina Drazoxolone; edifenfos; epoxiconazole; etaboxam; etirimol; etridiazole; famoxadone; fenamidone; fenapanil; fenarimol; fenbuconazole; fenfuram; fenhexamide; phenytopane; phenoxanyl; fenpiclonil; phenpropidine; fenpropimorf; ferbam; fluazinam; flubenzimine; fludioxonil; flumetover; flumorf; fluoromide; fluoxaestrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil; flutriafol; folpet; fosetyl-AI; fosetyl sodium; fuberidazole; furalaxyl; furametpir; flurcarbanyl; furmeciclox; guazatin; hexachlorobenzene; hexaconazole; himexazole; imazalil; imibenconazole; iminoctadine triacetate; tris (to the besylate) of iminoctadine; Idocarb, ipconazole; iprobenfos; iprodione; iprovalicarb; irumamycin; isoprothiolane; isovaledione; kasugamycin; kresoxima-methyl; mancozeb; maneb; meferimzone; mepanipyrim; mepronil; metalaxyl; metalaxyl-M, metconazole; metasulfocarb; metafurexam; 1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1 H-imidazole-5-carboxylic acid methyl ester; 2 - [[[[cyclopropyl [(4- (methoxyphenyl) imino] methyl] thio] methyl] -alpha- (methoxymethylene) -benzene-acetate-methyl: 2- [2- [3- (4-chlorophenyl) -1-methylaminideneaminoxymethyl] methyl-phenyl] -3-methoxyacrylate, methiram, methominoestrobin, metrafenone, metsulfovax, mildiomycin, monopotassium carbonate, myclobutanil, myclozoline, N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formylamino-2- hydroxybenzamide; N- (6-methoxy-3-pyridinyl) -cyclopropanecarboxamide; N-butyl-8- (1,1-dimethylethyl) -1-oxa-spiro [4.5] decan-3-amine; natamycin; nitrotal-isopropyl; noviflumuron; nuarimol; ofurace, orysastrobin, oxadixyl, oxolinic acid, oxpoconazole, oxycarboxin; oxifentiína, paclobutrazol, pefurazoate, penconazole, pencycuron, penthiopyrad, phosdiphen, phthalide, picobenzamid, picoxystrobin, piperalin, polyoxins, polioxorima; probenazole, prochloraz, procymidone, propamocarb Sodium propanosine, propiconazole, propineb, proquinazide, protioconazole; pyraclostrobin; pyrazophos; pirifenox; pyrimethanil; pyroquilon; piroxifur; pyrrolnitrine; quinconazole; quinoxifene; quintozene; siltiofam; symeconazole; sodium tetrathiocarbonate; Spiroxamine; sulfur; tebuconazole; tecloftalamo; tecnazeno; tetciclacis; tetraconazole; thiabendazole, ticiofen; tifluzamide; thiophanamate; tiram; thiadinyl; thioximide; tolclofos-methyl; tolylfluanide; triadimefon; triadimenol; triazabutyl; triazoxide; tricyclamide; tricyclazole; tridemorf; trifloxiestrobin; triflumizole; triforine, triticonazole; uniconazole; validamycin A; vinclozolin; zineb; ziram; zoxamide; (2 S) -N- [2- [4 - [[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl-3-methyl-2 - [(methylsulfonyl) amino] -butanamide; 1- (1-naphthalenyl) -1H-pyrrole-2,5-dione; 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine; 2,4-Dihydro-5-methoxy-2-methyl-4 - [[[[1- [3- (trifluoromethyl) -phenyl] -ethylidene] -amino] -oxy] -methyl] -phenyl] -3H-1 , 2,3-triazol-3-one; 2-amino-4-methyl-N-phenyl-5-thiazo-carboxamide; 2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1 H -inden-4-yl) -3-pyridinecarboxamide; 3,4,5-trichloro-2,6-pyridine-dicarbonitrile; 3 - [(3-bromo-6-fluoro-2-methyl-1 H-indol-1-yl) -sulfonyl] -N, N-dimethyl-1H-1, 2,4-triazole-1-sulfonamide; copper salts and copper formulations, such as the Bordeaux mixture; copper hydroxide; copper naphthenate; Copper oxychloride; copper sulphate; cufraneb; cuprous oxide; mancobre oxina-copper; alanicarb; aldicarb; aldoxicarb; alixicarb, aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxicarboxim, carbaryl, carbofuran, carbosulfan, cloetocarb, dimethylan, etiofencarb, fenobucarb, phenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl; metolcarb, oxamyl, pirimicarb, promecarb, propoxur; thiodicarb, thiofanox, trimetacarb, XMC, xylilcarb, acephate, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromophenvinphos (-methyl), butathiophos, cadusafos, carbophenotion, chloroethoxyphos, chlorfenvinphos, chlormefos, chlorpyrifos (-methyl) ethyl), coumaphos, cyanopheres, cyanophos, chlorfenvinphos, demeton-S-methyl, demeton-S-methylsulfone, dialiphos, diazinone, diclofention, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, dioxabenzophos, disulfoton, EPN, ethion, ethoprofos, etrimphos, famfur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupirazophos, fonophos, formothion, fosmetilane, fosthiazate, heptenophos, iodophenfenfos, iprobenfos, isazofos, isofenfos, isopropyl O -salicylate, isoxatión, malathion, mecarbam, methacryphos, methamidophos, methidathion, mevinfos, monocrotofos, naled, ometoato, oxidemetona-methyl; parathion (-methyl / -ethyl), phenoate, phorate, phosalone, fosmet, phosphamidone, phosphocarb, foxima, pirimiphos (-methyl / -ethyl), profenofos, propafos, propetamfos, protiofos, protoato, piraclofos, pyridafentión, piridatión, quinalfos, sebufos, sulfotep, sulprofos, tebupirimfos, temefos, terbufos, tetrachlorovinfos, thiometone, triazofos, triclorfón, vamidotión, acrinatrina, alletrina (d-cis-trans, d-trans), beta-ciflutrina, bifentrina, bioaletrina, S-ciclopentílico isomer of bioallethrin, bioetanometrin, biopermethrin, bioresmethrin, clovaportrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocitrin, cycloprotrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta, zeta-), cyphenothrin, deltamethrin, empentrin ( isomer 1R), esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenpiritrin, fenvalerate, flubrocitrinate, flucitrinate, flufenprox, flumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprotrin, kadetrin, lambda-cyhalothrin, metofluthrin, permethrin a (cis-, trans-), phenothrin (1-R-trans isomer), praletrin, profluthrin, protrifenbute, piresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, trefluthrin, teralethrin, tetramethrin (1 R isomer), tralometrine, transfluthrin, ZXI 8901, pyrethrins (pyrethrum), DDT, indoxacarb, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nitiazine, thiaclopride, thiamethoxam, nicotine, bensultap, cartap, camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor spinosad, acetoprol, ethiprole, fipronil, vaniliprole, avermectin, emamectin, emamectin benzoate, ivermectin, milbemycin, diofenolane, epophenone, phenoxycarb, hydroprene, kinoprene, methoprene, pyriproxyfen, triprene, chromafenozide, halofenozide, methoxyfenozide, tebufenozide, bistrifluron , clofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron, buprofezin, ciromaz ina, diafenthiuron, azocyclotin, cyhexatin, fenbutatin-oxide, chlorfenapyr, binapacril, dinobutone, dinocap, DNOC, fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpirad, hydramethylnon, dicofol, rotenone, acequinocyl, fluacripirima, strains of Bacillus thuringiensis, spirodiclofen , espiromesifen, carbonate of 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-aza-spiro [4.5] dec-3-en-4-yl and ethyl (alias: 3-ester) (2,5-Dimethylphenyl) -8-methoxy-2-oxo-1-aza-spiro [4.5] dec-3-en-4-yl and ethyl carbonic acid, CAS Reg no .: 382608-10 -8) and cis -3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-aza-spiro [4.5] dec-3-en-4-yl ester and ethyl ester of carbonic acid ( CAS Reg No .: 203313-25-1), flonicamide, amitraz, propargite, N2- [1,1-dimethyl-2- (methylsulfonyl) ethyl] -3-iodo-N 1 - [2-methyl-4 - [1, 2,2,2-tetrafluoro-1 - (trifluoromethylethyl) -ethyl] phenyl] -1,2-benzenedicarboxamide (CAS Reg .: 272451-65-7), thiocyclic hydrogen oxalate, thiosultap- sodium, azadirachtin, Baci llus spec, Beauveria spec., codlemone, etarrhizium spec., Paecilomyces spec., turingiensin, Verticillum spec., aluminum phosphide, methyl bromide, sulfuryl fluoride, cryolite, flonicamide, pymetrozine, clofentezine, etoxazole, hexythiazox, amidoflumet, benclotiaz , benzoximate, bifenazato, bromopropilato, buprofezina, quinometionato, clordimeform, chlorobenzilate, chloropicrina, clotiazoben, cicloprene, diciclanilo, fenoxacrima, fentrifanilo, flubenzimina, flufenerima, flutenzina, gosiplure, hidrametiinona, japonilure, methoxadiazona, petroleum, piperonilo butoxide, oleato of potassium , pyradalyl, sulfluramide, tetradifon, tetrasul, thiaratene and verbutin. Another aspect of the invention is a method for regulating growth in plant tissues of monocotyledonous or dicotyledonous plants, said method comprising applying to plant tissue cultures an appropriate amount of a compound having the formula (I), either alone or together with at least one additional active compound selected from among the set of plant growth regulating agents or plant hormones. The compounds of the formula (I) can preferably be used as plant growth regulating agents in monocotyledonous or dicotyledonous cultivated plants., preferably selected from among the set of economically important field-grown plants, such as, for example, wheat, barley, rye, triticale, rice, corn, sugar beet, cotton, or soybean, particularly corn, wheat and soybeans, as well as vegetables and ornamental plants, which have been made of this nature through genetic engineering. Traditional ways of generating new plants that have modified characteristics compared to existing plants, consist, for example, in traditional methods of cultivation and in the generation of mutants. However, it is also possible to generate new plants with altered characteristics with the aid of genetic engineering methods (see, for example, EP-A-0221044 and EP-A-0131624). For example, several cases of genetic engineering modifications of cultivated plants have been described for the purpose of modifying the starch synthesized in the plants (see, for example, WO 92/11376, WO 92/14827, WO 91/19806), - transgenic cultivated plants that are resistant to certain glufosinate type herbicides (compare, for example, EP-A-0242236, EP-A-242246) or glyphosate type (WO 92/00377) or type of sulfonylureas (EP-A-0257993 and US-A-5013659), - transgenic cultivated plants, for example cotton, which are capable of producing Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to specific pests ( EP-A-0142924, EP-A-0193259), - transgenic cultured plants whose fatty acid spectrum has been modified (WO 91/13972). A large number of techniques in molecular biology, by means of which new transgenic plants with altered characteristics can be generated, are known in principle; see, for example, the citations of Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd edition, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y .; or from Winnacker "Gene und Klone" [Genes and clones], VCH Weinheim, 2nd edition 1996, or from Christou, "Trends in Plant Science" [Trends in plant science] 1 (1996), 423-431). In order to perform such manipulations by genetic engineering, nucleic acid molecules can be introduced into plasmids, which allow mutagenesis or a change of sequences by means of a recombination of DNA sequences. It is possible, for example, with the help of the aforementioned classical methods, to perform base exchanges, eliminate subsequences or add natural or synthetic sequences. To connect the DNA fragments with one another, adapters or crimpers can be attached to the fragments. For example, plant cells can be generated with reduced activity of a gene product, by expressing at least one corresponding antisense RNA, an RNA of the same sense to achieve a concomitant suppressive effect, or by expressing at least one ribozyme of appropriate construction, which specifically dissociates transcripts of the aforementioned gene product. For this purpose, it is possible to make use, on the one hand, of DNA molecules that span the entire coding sequence of a gene product, including any flanking sequences that may be present, and, on the other hand, of DNA molecules that only they encompass parts of the coding sequence, but these parts must be sufficiently long in order to produce an antisense effect in the cells. One can also make use of DNA sequences which show a high degree of homology with the coding sequences of a gene product, but which are not completely identical. When nucleic acid molecules are expressed in plants, the protein that has been synthesized can be located in any desired compartment of the plant cell. However, in order to achieve a location in a particular compartment, it is possible, for example, to link the coding region with DNA sequences that guarantee localization in a particular compartment. Such sequences are known to a skilled professional (see, for example, the citations of Braun et al., EMBO J. 11 (1992), 3,219-3,227, Wolter et al., Proc. Nat. Acad. Sci. USA 85 (1988). , 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).

The cells of transgenic plants can be regenerated by known techniques to give whole plants. In principle, the transgenic plants can be plants of any desired plant species, ie monocotyledonous and also dicotyledonous plants. This allows transgenic plants that exhibit altered characteristics to be obtained by overexpression, suppression or inhibition of genes or sequences of homologous genes (= natural), or by expression of genes or sequences of heterologous (= foreign) genes. The compounds of the formula (I) can preferably be used in transgenic plant cultures which are resistant to herbicides taken from the group of sulfonylureas, glufosinateammonium or glyphosatoisopropylammonium and analogous active substances which show altered phenotypes, such as, but not limited to , characteristics such as a modification of the content, an altered flowering time, male or female sterile plants, plants resistant to the environment due to an expression or repression of endogenous or exogenous genes in the cultivated transgenic plant. The use according to the invention for the regulation of the growth of plants also includes the case in which the compounds of the formula (I) are formed only in the plant or in the soil from a precursor ("prodrug"). ") after its application to the plant.

The compounds of the formula (I) can be used in conventional formulations such as wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules. The invention therefore also relates to plant growth regulating compositions comprising compounds of the formula (I). According to a further feature of the present invention, there is provided a plant growth regulating composition, comprising an effective amount of a compound of the formula (I), as defined above, or an acceptable salt in agriculture thereof, in association with, and preferably homogeneously dispersed in, one or more diluents or carriers acceptable in agriculture and compatible, and / or agents with surface activity [i.e., diluents or carriers and / or agents with surface activity of the type generally accepted in the art as suitable for use in herbicidal compositions, and which are compatible with the compounds of the invention]. The term "homogeneously dispersed" is used to include compositions in which the compounds of the formula (I) are dissolved in other components. The term "growth regulating composition" is used in a broad sense, to include not only compositions that are ready for use as herbicides, but also concentrates that must be diluted before use (including tank mixes).

The compounds of the formula (I) can be formulated in various ways, depending on the prevailing biological and / or chemical-physical parameters. Examples of possible formulations that are appropriate are: wettable powders (WP), water soluble powders (SP), water soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as emulsions of the oil in water type and water in oil, sprayable solutions, concentrates to suspend (SC), dispersions on an oil or water base, solutions that are miscible with an oil, suspensions to encapsulate (CS), dusting powder (DP), seed disinfectant products granules for spreading and for application on the ground, granules (GR) in the form of microgranules, granules formed by projection, coated granules and granules formed by adsorption, granules dispersible in water (WG), granules soluble in water (SG) , ULV formulations (ultra high volume), microcapsules and waxes. These types of individual formulations are known in principle and are described, for example, in the works of: Winnacker-Küchler, "Chemische Technologie" [Chemical Technology], volume 7, C. Hauser publishing house, Munich, 4th edition of 1986; Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973; K. Martens, "Spray Drying Handbook", 3rd edition, G. Goodwin Ltd, London, 1979; The necessary formulation aids, such as inert materials, surfactants, solvents and other additives, are also known, and are described, for example, in the works of: Watkins, "Handbook of Insecticide Dust Diluents and Carriers". diluents and fine powder insecticide supports], 2nd edition, Darland Books, Caldwell NJ; H.v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd edition, J. Wiley & Sons, N.Y .; C. Marsden, "Solvents Guide" [Solvent Guide], 2nd edition, Interscience, N.Y. 1963; "Detergents and Emulsifiers Annual" by McCutcheon, MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, "Grenzfláchenaktive Áthylenoxidaddukte" [Adducts with interfacially active ethylene oxide], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie" [Chemical Technology], volume 7, editorial C. Hauser Munich, 4th edition, 1986. Based on these formulations, it is also possible to prepare combinations with active substances such as pesticides, such as, for example, insecticides , acaricides, herbicides, fungicides, and with antidotes, fertilizers and / or growth regulators, for example in the form of a prepared mixture or a mixture in storage. Wettable powders are formulations which are uniformly dispersible in water and which, in addition to the compounds of the formula (I), also comprise ionic and / or nonionic surfactants (wetting agents, dispersants), for example poly (oxyethylated) alkylphenols, alcohols poly (oxyethylated) fatty amines, poly (oxyethylated) fatty amines, (fatty alcohol) -polyglycol ether sulfates, alkane sulphonates or alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, dibutylnaphthalene sulfonate sodium or sodium oleoylmethyltaurate, in addition to a diluent or inert substance. To prepare the wettable powders, the compounds of the formula (I) are, for example, finely ground in conventional apparatuses such as hammer mills, blower mills and air jet mills, and mixed with the formulation aids, and either concomitantly or following this. The emulsifiable concentrates are prepared, for example, by dissolving the compounds of the formula (I) in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or aromatics or high-boiling hydrocarbons or mixtures thereof, with addition of one or more ionic and / or nonionic surfactants (emulsifiers). Emulsifiers which may be used are, for example: calcium salts of alkylarylsulfonic acids, such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers, such as polyglycol esters of fatty acids, alkylaryl polyglycol ethers, (fatty alcohol) polyglycol ethers, condensates of propylene oxide and ethylene oxide, alkylpolyethers, sorbitan esters, such as esters with sorbitan fatty acids or poly (oxyethylene) sorbitan esters, such as poly (oxyethylene) esters with sorbitan fatty acids.

The dusts are obtained by grinding the active substance with finely divided solid substances, for example talc or natural clays, such as kaolin, bentonite or pyrophyllite, or diatomaceous earth. The concentrates for suspending may be based on water or an oil. They can be prepared, for example, by wet grinding by means of commercially available bead mills, if appropriate with the addition of surfactants, as already mentioned above for example in the case of the other types of formulations. Emulsions, for example oil-in-water (EW) type emulsions, can be prepared for example by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and, if appropriate, surfactants, such as those they have already been mentioned above, for example, in the case of the other types of formulations. The granulates can be prepared either by casting the compounds of the formula (I) on an inert granulated adsorbent material, or by applying concentrates of active substances on the surface of supports such as sand, kaolinites or an inert granulated material, by means of binding agents. , for example, a polyvinyl alcohol, a poly (sodium acrylate), or alternatively mineral oils. Suitable active substances can also be granulated in the manner that is conventional for the production of granules of fertilizers, if desired in a mixture with fertilizers. The water-dispersible granules are prepared, as a rule, by standard methods, such as spray drying, fluidized-bed granulation, disk granulation, mixing in high-speed mixers and extrusion without any solid inert material. For preparing disc-shaped, fluidized bed, extruder and projection granules, see, for example, the procedures outlined in the works: "Spray Drying Handbook", 3rd edition of 1979, G. Goodwin Ltd, London; J.E. Browning, "Agglomeration" (Agglomeration), Chemical and Engineering 1967, pages 147 et seq .; "Perry's Chemical Engineer = s Handbook," 5th edition, McGraw-Hill, New York 1973, pages 8-57. For more details about the formulation of agents for the protection of cultivated plants, see, for example, the works of G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th edition, Blackwell Scientific Publications, Oxford, 1968, pages 101-103. As a general rule, agrochemical formulations comprise from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds of the formula (I).

The concentration of compounds of the formula (I) in wettable powders is, for example, from about 10 to 90% by weight, the remainder being made up to 100% by weight by common formulation components. In the case of emulsifiable concentrates, the concentration of compounds of the formula (I) can be up to about 1 to 90, preferably 5 to 80% by weight. The formulations in the form of the dusts are usually from 1 to 30% by weight of compounds of the formula (I), preferably in most cases from 5 to 20% by weight of the compounds of the formula (I) ), while the projected solutions comprise approximately 0.05 to 80, preferably 2 to 50% by weight, of compounds of the formula (I). In the case of water-dispersible granules, the content of compounds of the formula (I) depends in part on whether the compounds of the formula (I) are in a liquid or solid form, and of which the granulation aids are, loading and filling materials and the like that are being used. The dispersible granules in water, for example, they comprise between 1 and 95% by weight of an active substance, preferably between 10 and 80% by weight. In addition, the formulations of compounds of the formula (I) mentioned, if appropriate, comprise adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze and antifreeze agents, solvents, fillers and fillers, supports, dyes, defoamers, evaporation inhibitors, pH regulators and viscosity regulators, which are conventional in each case. Appropriate formulations are known for plant growth regulating compositions. A description of suitable formulations that can be used in the method of the invention can be found in the international patent publications WO 87/3781, WO 93/6089 and WO 94/21606 as well as in the European patent application EP 295117 and in U.S. Patent 5,232,940, Formulations or compositions intended for uses in the regulation of plant growth can be produced in a similar manner, by adapting the ingredients, if necessary, to make them more appropriate for the plant or the plant. floor in which the application has to be made. The compounds of the formula (I) or their salts can be used as such or in the form of their preparations (formulations) as combinations with other active substances such as pesticides such as, for example, insecticides, acaricides, nematicides, herbicides, fungicides, antidotes, fertilizers and / or other growth regulating agents, for example as a premix or as a tank mix. It has been found that, surprisingly, the compounds of the formula (I) and in a very special way the compounds 1.1; 1.2 1.3; 1.4; 1.5; 1.6; 1.7; 1.8; 1.9; 1.10; 1.11; 1.12; 1.13; 1.34; 1.35; 1.36; 1.37 1.65; 1.96; 1.123; 1,133; 1,134; 1,135; 1,136; 1,137; 1,138; 1,139; 1,140 1,141; 1,142; 1,143; 1,144; 1,145; 1,166; 1,167; 1,168; 1,169; 1,197; 1,228 1,255; 1,268; 1,329; 1.399; 1,400; 1,461; 1.532; 1,664; 1,796; 2.1; 2.10; 2.11; 3.2; 3.3; 3.4; and 3.10 play an important role in regard to the growth properties of the plants, which may be different due to an application to various cultivated plants. For example, compound 1136 shows significant effects of approximately the same magnitude when used as a regulatory agent of plant growth in corn and wheat, but in different concentrations. Compound 1141 shows a remarkable effect as a plant growth regulating agent in corn and a superior effect in wheat. By virtue of the practice of the present invention a wide variety of plant growth responses can be induced, including the following ones (enumeration without order of importance): a) a more developed system of roots b) increase of shoot formation c) increase in the height of the plants d) larger sheet of the leaves e) less dead basal leaves f) stronger shoots g) green color of the leaves h) less fertilizers are needed i) fewer seeds are needed j) more productive shoots k) less third non-productive shoots I) earlier flowering m) early maturity of the grains n) less overturning of the plants (bedding) o) longer panicles p) increased growth of the shoots q) improved vigor of the plants r) early germination s) more fruits and better yield. It is intended that, as used herein, the term "method for the regulation of plant growth" or "plant growth regulation" means the achievement of any of the nineteen categories of responses that were previously have mentioned or any other modification of a plant, a seed, a fruit or a legume (regardless of whether the fruit or the vegetable is harvested or not harvested) as long as the net result is to increase growth or profit for any plant, seed, fruit or vegetable property as distinct from any pesticide action (unless the present invention is practiced in conjunction with, or in the presence of, a pesticide, eg, a herbicide). The term "fruit" as used in the present specification, is to be understood as meaning anything of economic value that is produced by the plant.

Preferably, at least an increase of 10% of one or more of the respective growth responses of the plants is obtained.

The 5-amino-1-arylpyrazole-3-carboxylic acid derivative of the formula (I) can be applied for purposes of regulating the growth of plants to the foliage of plants and / or to the soil in which said plants are growing. Applications to the soil are often carried out in the form of granules, which are usually applied in an amount sufficient to provide a rate from about 0.00001 kg / ha to about 0.5 kg / ha of the active ingredient, preferably between 0.00001 and 0.1 kg / ha, more preferably between 0.00001 kg / ha and 0.01 kg / ha. A preferred embodiment of the invention consists in a method for the regulation of the growth of the plants, which comprises applying to the seeds from which said plants grow, before said sowings, a non-phytotoxic amount effective to regulate the growth of the plants. plants, of a compound having the formula (I). The seeds can be treated, especially by coating or embedding or impregnation or soaking or immersion in liquid or pasty formulations, which are known per se, and subsequently can be dried. The seeds comprising from 0.1 to 1000 grams (g) per 100 kilograms (kg) of a compound of the formula (I), preferably from 0.1 to 800 g per 100 kg, most preferably from 0.1 to 250 g per 100 kg, they are particularly appropriate for this purpose. The exact amount of the 5-amino-1-arylpyrazole-3-carboxylic acid derivative of the formula (I), which is to be used, will depend, among other things, on the particular species of plant being treated. An appropriate dose can be determined by a person skilled in the art by routine experimentation. The response of the plant will depend on the total amount of compound used, as well as the particular species of plant being treated. Of course, the amount of the 5-amino-1-arylpyrazole-3-carboxylic acid derivative of the formula (I) should not be phytotoxic with respect to the plant being treated. Although the preferred method of application of the compounds used in the process of this invention is directed directly to the foliage and stems of the plants, the compounds can be applied to the soil in which the plants are growing. The following examples are illustrative of methods for regulating the growth of plants according to the invention, but should not be understood as limiting the invention, since certain modifications in materials and methods will be apparent to a skilled artisan. All measurements of plant growth regulating effects were determined either using a protoplast scrutiny assay and / or using a root growth assay and / or by applying the previously selected compounds to the above defined test system under natural conditions of growth in tests in the field. In all cases, protoplasts, plants or parts of plants or untreated seeds were taken as controls.

B. BIOLOGICAL EXAMPLES EXAMPLE 1 Plant protoplast system The present invention features a so-called high-flow rate assay for rapid screening of chemical compounds that modulate cell growth. The test generally involves: a) protoplasts from plants that have grown in a liquid medium, b) a library of chemical compounds, and c) screening the protoplasts to identify compounds that significantly affect the growth and development of the cells.

Preparation of the protoplasts Preferably, the protoplasts were prepared from suspensions of cells derived from corn stems. The protoplasts were obtained by enzymatic digestion of the aggregates of cells in the suspension. The cells were digested for 3-6 hours at room temperature in a mixture of cellulase and pectolyase, the protoplasts were released by gentle shaking, filtered through a 45 μm mesh and collected by centrifugation. After digestion, the protoplasts were washed several times to remove cell debris and enzyme debris, and then resuspended in a culture medium. The protoplasts were plated in 50-100 μl aliquots into microtiter wells with a density ranging from 100,000 to 2,000,000 protoplasts per ml, preferably at a concentration of 800,000 protoplasts / ml.

Screening assay To identify chemical compounds that modulate cell growth, corn protoplasts were incubated with a library of chemical compounds in 96-well microtiter plates. After incubation at 25 ° C for 1-14 days, preferably 7-10 days, the protein content was measured by colorimetric assays based on Coomassie dye. The growth of the cells treated with the chemical compounds involved in the assay was detected by comparison with untreated protoplasts. The treatment with a section of compounds derived from the formula (I) shows an increase of more than 50% with respect to an untreated control.

EXAMPLE 2 Root growth test The roots of the plants are a proliferative tissue in high degree, which allows an easily accessible, cheap and short term method of scrutiny, for agents that regulate the growth of plants. The results obtained can easily be transferred to the overall effects on a plant of the growth regulating agents of the plants identified by said system. Using this root test, it is possible for a person to determine the effect of a seed treatment for root growth and / or germination and / or changes in the habitat of germinated plants in order to identify possible use as a performance enhancing agent. Two seeds of wheat (Triticum aestivum, variety "TRISO") or 1 seed of corn (Zea mays, variety "LORENZO") per hole in a tray of plastic material containing an architecture of 8 x 13 holes, were placed on a soil with compost, covered with sand. These seeds were treated 100 μl / hole, which creates an application volume of approximately 1200 l / ha, of a solution of a compound at active ingredient regimes equivalent to 100, 10 and 1 g ai / ha of each compound using a robotic application system (Lizzy Spray Robotics). Six replications were made in a row of each compound and each concentration. The outer edge of the plastic material tray, which was previously defined, was left untreated to avoid false negative effects and the central row (No. 7) was used as an untreated control. The treated seeds were allowed to dry for approximately 4 hours and subsequently were covered with sand and watered. The trays were stored in chambers with 14 hours of illumination at a temperature of 24 ° C (± 2) during the day and 16 ° C (± 2) at night and with a relative humidity (hr) of 60%, and They were watered daily. The determinations were made at 16 (± 2) days after the treatment, recounting the germinated plants and checking the symptoms and the phytotoxicity percentage. In addition, the roots were washed and the rods were cut directly above the seeds and the wet roots were placed on dry paper towels for approximately 30 minutes and weighed later. This procedure provides a similar degree of moisture to the roots, so that a comparison of the weights is possible. Table 4 shows the results of some of the compounds (Cpd) claimed as being effective in regulating the growth of plants in regard to corn. The effects observed in regard to the Root Growth outlined in column 2 (a Root Growth of "100" is established as the pattern) are directed to concentrations that are equivalent to 100, 10, 1 g of ia / ha, of each one.

TABLE 4 Table 5 shows the results of some of the compounds (Cpd) claimed as being effective in regulating the growth of plants as regards wheat. The effects observed in regard to Root Growth reported in column 2 (a root growth of "100" is established as the standard) are directed to concentrations that are equivalent to 100, 10, 1 g ai / ha, of each one.

TABLE 5 EXAMPLE 3 Test in the field Magister and Zamora hybrid corn seeds were seeded and treated with compound 1136 at the rate of 1 g / 100 kg of seeds (0.0003 kg / ha).

The field tests were established in a dissociated plot design, which represents the plants treated with compounds of the formula (I) as well as the untreated control plants. The results showed an increase in grain yield of up to 119% in the case of the Magister hybrid and up to 131% in the case of the Zamora hybrid, compared to the yield obtained with untreated control plants in each case.

Claims (13)

NOVELTY OF THE INVENTION CLAIMS

1. - The use of a compound of the formula (I) or of an acceptable salt in agriculture thereof for the regulation of the growth of the plants (i) wherein: R1 is CONR6R7 or CO2R8; W is C-halogen or N; R2 is H or S (O) mR9; R3 is NR10R11, halogen, OH, C6-C6 alkoxy, C2-C6-oxy alkenyl or C2-C2-oxy alkynyl; R4 is H or halogen; R5 is C1-C4 haloalkyl or C1-C4 haloalkoxy; R6 is H, Ci-Cß alkyl, Ci-Cß haloalkyl, C?-C6 alkoxy Ct-Cß alkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 haloalkynyl -C6, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C6 alkyl, C6-C6 alkoxy, C6-thio alkyl, (CH2) nR12, (CH2) PR13, C-alkyl? -C6-CN, CrC6-NR10R11 alkyl or C6-S (0) rR9 alkyl; R7 is H, C? -C6 alkyl, C3-C6 alkenyl or C3-C6 alkynyl; or R6 and R7 together with the N atom attached thereto, form a saturated five or six membered ring, which optionally contains an additional ring heteroatom, which is selected from O, S and N, the ring being unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, C6 alkyl, and CrC6 haloalkyl; R8 is H, CrC6 alkyl, C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl or (CH2) nR12; R9 is CrC6 alkyl or C6-C6 haloalkyl; R10 and R11 are each independently H, Ci-Cß alkyl, Ci-Cß haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, cycloalkyl of C3-C6-C6-C6 alkyl, COR14 or CO2R15; or R10 and R11 in common with the N atom attached thereto, form a saturated five or six membered ring, which optionally contains an additional ring heteroatom, which is selected from O, S and N, the ring being unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, Ci-Cß alkyl and C-pCβ haloalkyl; R12 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, CrC6 alkyl, Ci-Cß haloalkyl, C6C6 alkoxy, CrC6 haloalkoxy, CO2R16, CN, NO2, S ( 0) qR9, COR16, CONR16R17 and OH; R13 is heterocyclyl unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, NO2, CN, CO2R16 , S (0) qR9, OH and oxo; R14 and R15 are each independently H, CI-CT alkyl, Ci-Cß haloalkyl, C2-C6 alkenyl, C2-Ce haloalkenyl, C2-Cs alkynyl or Ci-C3-alkyl alkoxy of C1-C4; R16 and R17 are each independently of H, Ci-Cß haloalkyl or haloalkyl; m, q and r are, each independently, 0, 1 or 2; n and p are, each independently, 0, 1, 2, 3 or 4; and each heterocyclyl in the aforementioned radicals is independently a heterocyclic radical having from 3 to 7 ring atoms and 1, 2 or 3 heteroatoms in the ring, selected from the group consisting of N, O and S. 2.- The use of a compound as defined in claim 1, wherein R1 is CONR6R7; W is C-CI or C-Br; R2 is S (O) mR9, R3 is NR10R11, halogen, OH, C1-C3 alkoxy, C2-C6 alkenyl-oxy or C2-C6 alkynyl-oxy; R4 is Cl or Br; R5 is CF3 or OCF3; R 6 is H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 3 alkoxy C 1 -C 3 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 haloalkenyl, C 3 -C 4 alkynyl, C 3 haloalkynyl -C4, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C1-C3 alkoxy, C1-C3 alkylthio, (CH2) nR12 or (CH2) PR13; R7 is H, C4 alkyl, C3-C4 alkenyl or C3-C4 alkynyl; or preferably R6 and R7 in common with the N atom attached thereto, form a saturated five- or six-membered ring, which optionally contains an additional ring heteroatom, which is selected from O, S and N, the ring being replacing or substituted with one or more radicals selected from the group consisting of halogen, C1-C3 alkyl, and CrC3 haloalkyl; R9 is C1-C3 alkyl or C1-C3 haloalkyl (more preferably R9 is CF3; R10 and R11 are each independently H, C1-C3 alkyl, C1-C3 haloalkyl, C3-C alkenyl , C3-C4 haloalkenyl, C3-C4 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C3 alkyl, COR14 or C02R15; or R0 and R11 in common with the N atom attached thereto , form a saturated ring of five or six members, which optionally contains an additional heteroatom in the ring, which is selected from O, S and N, the ring being unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, C1-C3 alkyl and C1-C3 haloalkyl: R12 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1 alkoxy -C3, C3 haloalkoxy, CO2R16, CN, NO2, S (O) qR9, COR16, CONR16R17, NR16R17 and OH; R13 is unsubstituted or substituted heterocyclyl containing one or more radicals selected from the group consisting of halogen, C1-C3 alkyl, haloalkyl of C? -C3, alkoxy of C? -C3, haloalkoxy of C? -C3, NO2, CN, CO2R16, S ( O) qR9, OH and oxo; R 14 and R 15 are each independently H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 3 alkenyl, C 2 -C 3 haloalkenyl, C 3 alkynyl or C 1 alkoxy; C6-C1-C4 alkyl; R 6 and R 17 are each independently H or C 1 -C 3 alkyl; and each heterocyclyl? in the aforementioned radicals it is independently a heterocyclic radical having from 3 to 6 ring atoms and 1, 2 or 3 heteroatoms in the ring, selected in the set consisting of N, O and S. 3.- The use of a compound as defined in claim 1, wherein R1 is CONR6R7; W is C-CI; R2 is H, or S (0) mR9, R3 is NR10R11, halogen, OH or C ^ alkoxy; R4 is Cl; R5 is CF3; R6 is H, C1-C4 alkyl, C3-C3 alkoxy C1-C2 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C3-C3 cycloalkyl, C3-C6 cycloalkyl-C1 alkyl -C2, C? -C3 alkoxy, CrC3-thio alkyl, (CH2) nR12 or (CH

2) PR13; R 7 is H, C 1 -C 3 alkyl, C 3 -C alkenyl or C 3 -C 4 alkynyl; R9 is methyl, ethyl or CF3; R10 and R11 are each independently H, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 alkenyl, C3-C4 haloalkenyl, C3-C4 alkynyl, C3-C6 cycloalkyl, cycloalkyl of C3-C6-alkyl of C -? - C

3) COR14 or C02R15; R12 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, C1-C3 alkyl, C1-C3 haloalkyl, C3 alkyl alkoxy, C1-C3 haloalkoxy, CO2R16, CN and NO2; R13 is heterocyclyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, C1-C3 alkyl, C1-C3 haloalkyl, d-C3 alkoxy, C1-C3 haloalkoxy, NO2, CN, CO2R16 , S (O) qR9, OH and oxo; R 14 and R 15 are each independently C 1 -C 3 alkyl; R 16 and R 17 are each independently H or C 1 -C 3 alkyl; and each heterocyclyl in the aforementioned radicals is independently a heterocyclic radical having from 3 to 6 ring atoms and 1, 2 or 3 heteroatoms in the ring, selected in the set consisting of N, O and S.

4. The use of a compound as defined in claim 1, wherein R1 is CONR6R7; W is C-CI; R2 is H, or S (0) mR9; R3 is NHR10; R4 is Cl; R5 is CF3; R 6 is H, C 1 -C 5 alkyl, d-C 2 alkoxy C 1 -C 2 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl CrC2, furfuryl or tetrahydrofurfuryl; R7 is H or C1-C3 alkyl, R9 is methyl, ethyl or CF3; and R10 is H, methyl or ethyl.

5. The use of a compound as defined in claim 1, wherein R1 is CO2R8; W is C-CI; R2 is H, or S (O) mR9; R3 is NR10R11; R4es Cl; R5 is CF3; R8 is H, methyl or ethyl; R9 is methyl, ethyl or CF3; R10 is H, methyl or ethyl; and R11 is H.

6. The use of a compound as defined in claim 1, wherein R1 is CONR6R7.; W is C-CI; R2 is S (O) mCF3; R3 is NR10R11, halogen, OH or d-C2 alkyl; R4 is Cl; R5 is CF3; R6 is H or C? -C3-thio alkyl; R7 is H; R10 is CrC3 alkyl, COR14 or CO2R15; R11, R14 and R15 are each independently C1-C3 alkyl.

7. A composition for the regulation of the growth of plants, comprising one or more compounds of the formula (I) as defined in any one of claims 1 to 6 or an acceptable salt in agriculture thereof , supports and / or surfactants useful for plant protection formulations.

8. The composition according to claim 7, further characterized in that it comprises an additional active compound selected from the group consisting of acaricides, fungicides, herbicides, insecticides, nematicides or plant growth regulating substances, which are not identical to compounds defined by formula (I) of claim 1.

9. - The use of a composition as defined in any one of claims 7 to 8 for the regulation of plant growth, wherein the plant is a monocot or dicotyledonous cultivated plant.

10. The use claimed in claim 9, wherein the plant is selected from the group consisting of wheat, barley, rye, triticale, rice, corn, sugar beet, cotton or soybeans.

11. A method for the regulation of growth in cultivated plants, which comprises applying an effective amount of a compound of the formula (I) as defined in claims 1 to 6, to the site where the action, said method comprising applying to plants, seeds from which they grow or to the locus in which they grow, a non-phytotoxic amount effective to regulate the growth of the plants, of one or more compounds of the formula (I ).

12. The method according to claim 11, further characterized in that it results in an increase in yield of at least 10% as regards the plants to which it is applied.

13. A compound as defined by formula (I), or a salt thereof, wherein: i) R1 is CO2R8; R2 is H or S (0) mR9; R3, R4, R5, W and m are as defined above; R8 is H; and R9 is C-C6 alkyl or d-C6 haloalkyl; or ii) R1 is CONR6R7; R6 is C?-C6 alkyl, d-C6 haloalkyl, Ci-Cß alkoxy -C -C alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C6-C6 alkyl, C6-C6 alkoxy, C6-thio alkyl, (CH2) nR12, (CH2) pR13, d-C6-alkyl, alkyl of C C6-NR10R11 or C? -C6-S (O) rR9 alkyl; or R6 and R7 in common with the N atom attached thereto, form a saturated five or six membered ring, which optionally contains an additional ring heteroatom, which is selected from O, S and N, the ring being replacing or substituted with one or more radicals selected from the group consisting of halogen, d-Cβ alkyl and d-C6 haloalkyl; and R 2, R 3, R 4, R 5, R 7, R 9, R 10, R 11, R 12, R 13, W, n, p and r are as defined in formula (I); with the exclusion of the compound wherein: R1 is CON (CH3); R2 is CF3S; R3 is OH; R4 is Cl, R5 is CF3; and W is C-CI.