Compounds and composition for improving resistance to abiotic stress in plants

Abstract

The present invention relates to a compound and to an agrochemical composition comprising said compound useful in enhancing the resistance to abiotic stress in a plant, such as tomato, wheat or maize, said stress being caused for instance by drought.

Description

[0001] COMPOUNDS AND COMPOSITION FOR IMPROVING RESISTANCE TO ABIOTIC STRESS IN PLANTS FIELD OF THE INVENTION

[0001] The present invention relates to a compound and to an agrochemical composition comprising said compound useful in enhancing the resistance to abiotic stress in a plant, such as tomato, wheat or maize, said stress being caused for instance by drought. BACKGROUND

[0002] Global warning and climate change represent a severe threat for crop production, as the reduction of frequency of rain precipitations causes fields to turn into dust and renders water scarce, thus exposing crops to drought. The United Nations estimate that in 2050 about 75% of the world population will be affected by drought. In addition, drought frequency and duration has already increased by 29% since 2000. In this context, crop production is becoming more and more challenging and associated with increasing costs as crop yield and market price are vastly affected by drought. Solutions are thus in need to reduce the threat of drought by improving water management and / or improving the resistance to drought of crop plants.

[0003] Drought is a known cause of abiotic stress in plants. When exposed to abiotic stress, for example, drought, a plant usually closes its stomata to reduce water loss through transpiration and conserve as much water as possible. Abscisic acid (ABA) plays a fundamental role in this defense mechanism. Abscisic acid (ABA) ABA induces changes in the membrane potential and ion flow, which leads to alterations in the turgor of the occlusive cells and consequently the closure of stomata. Sheard, L. B., & Zheng, N. describe in «Plant biology: signal advance for abscisic acid.». Nature 2009, 4, 575-576 the mechanism of action of ABA. In the plant cell, ABA is perceived through its binding to soluble PYR / PYL receptors. ABA perception and signalling requires the binding of the ligand (ABA) by the PYR / PYL receptors and the interaction of the ligand and the receptor with the PP2Cs. The formation of Receptor- ABA-PP2C ternary complexes inhibits the phosphatase activity of PP2Cs, allowing SnRK2s to remain phosphorylated and active to mediate the activation of ABA- responsive ABFs / AREBs transcription factors and of different ion transporters. In the plasma membrane, phosphorylation of different K+transporters leads to inhibition of K+ influx and activation of K+efflux, which together with activation of R- and S-type anion channels and aquaporins lead to loss of turgor in guard cells and stomata closure. The activation of ABA receptors and, therefore, of this cascade signalling, promotes adaptation to stressful situations such as drought.

[0004] While ABA can be synthetically prepared and administered to plants in order to enhance their resistance to abiotic stress, there is a need for more active and / or accessible compounds susceptible of activating ABA receptors. In this regard, several ABA receptor agonist compounds have been reported in the literature. For instance, international patent applications WO2014 / 210555, WO2013 / 148339 and WO2017 / 034892 disclose ABA-receptor agonist compounds of general formula The disclosed compounds allow enhancing resistance to drought and prevent seed germination by activation of ABA receptors in plants. In addition, international patent application WO2023 / 067192 disclose further compounds based on the (dihydro)quinolinonyl sulfonamide scaffold as ABA receptor agonists. Quinabactin, sulfobactin and AMF4 represent well-known examples of such compounds: Further compounds based on small modifications of the ABA molecule are also disclosed in international application WO2008 / 094568. In addition, further sulfonamide compounds deprived of the (dihydro)quinolinonyl group depicted above are known in the art. A first example of such ABA agonist compounds is pyrabactin, disclosed in 2009 by Park et al. in Science, 2009, 324(5930), 1068- 1071. Also, Vaidya A.S. and co-workers disclose in ACS Chem. Biol., 2017, 12, 2842‐2848 the compound cyanabactin of formula It is further disclosed that the sulfonamide group and 4-methylbenzyl substructures of cyanabactin mimic ABA's carboxylate and C6 methyl group of ABA respectively. Cyanabactin is also disclosed in Frackenpohl, J. et al. Bioorganic & Medicinal Chemistry, Vol. 28, No. 22, p.115725. Additionally, opabactin compound was disclosed by Vaidya et al. in 2019 in Science, 2019, 366(6464). Opabactin was disclosed as being particularly active in enhancing the resistance to abiotic stress in plants such as wheat and tomato – in particular, opabactin is more active in preventing leaf transpiration than ABA, AMF4, or quinabactin. Also, it was shown in qRT-PCR assays that wheat plants treated with opabactin are more tolerant to drought than ABA, cyanabactin and quinobactin. The molecular formula of opabactin is as follows: opabactin

[0005] From what is disclosed in the art, it derives that there is still a need for providing further agonist compounds of the receptors of abscisic acid in plants, which exhibit in particular high activity in enhancing the resistance to abiotic stress in a broad range of plants such as tomato, wheat or maize, and / or which are easy to prepare. SUMMARY OF THE INVENTION

[0006] After exhaustive research, the inventors have developed a new family of sulfonamide compounds which are readily accessible synthetically and are highly active as agonists of ABA receptors. In particular embodiments, the compounds of the invention are surprisingly equally active or more active than ABA or than opabactin in enhancing resistance to abiotic stress in a plant. The compounds of the invention are advantageously particularly active in common crops, such as tomato, wheat and maize.

[0007] Thus, a first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein: each of R1 and R2 is independently selected from the group consisting of hydrogen, a linear or branched (C1-C6)alkyl group and a (C3-C6)cycloalkyl group and provided that at least one of R1 and R2 is other than hydrogen; and Z is a radical selected from the radicals of formula (A) and (B) (A) (B) wherein: Y is selected from the group consisting of O, NR3, CHR3 and C(R3)2; and each R3 is independently selected from the group consisting of hydrogen, fluoro and a linear or branched (C1-C6)alkyl group that is optionally substituted with one or more fluorine atoms.

[0008] A second aspect of the invention relates to a process for the preparation of a compound of formula (I) as defined in the first aspect of the invention comprising the step of contacting a compound of formula (II) with a compound of formula (III) in conditions sufficient for the formation of the compound of formula (I) (II) (III) wherein X is a halogen group and R1, R2 and Z are as defined in the first aspect of the invention.

[0009] A third aspect of the invention relates to an agrochemical composition comprising the compound according to the first aspect of the invention or a salt, a solvate, a stereoisomer or a deuterated analogue thereof, and an agrochemically acceptable carrier. Particular embodiments of the third aspects relate to sprayable compositions.

[0010] A fourth aspect of the invention relates to the use of the compound according to the first aspect of the invention or a salt, a solvate, a stereoisomer or a deuterated analogue thereof or of the agrochemical composition according to the third aspect of the invention in one or more of: (i) enhancing abiotic stress resistance in a plant, (ii) inhibiting seed germination in a plant, and / or (iii) reducing leaf transpiration in a plant.

[0011] A fifth aspect of the invention relates to a plant seed comprising or coated with the compound according to the first aspect of the invention or a salt, a solvate, a stereoisomer or a deuterated analogue thereof or the agrochemical composition according to the third aspect of the invention. BRIEF DESCRIPTION OF THE DRAWINGS

[0012] Fig.1 describes (a) In vivo activity of compounds of formula (I) on the germination of seeds of Arabidopsis thaliana (Arabidopsis) treated at 100 nM of ABA, AMF4 or opabactin (OP) or a compound of formula (I). (b-c) In vivo activity of compounds of formula (I) on seedling establishment of seeds of Arabidopsis treated at varying concentrations of the compound of formula (I). (d). Germination dose-response experiment to calculate IC50 of ABA, OP and (Ic).

[0013] Fig.2. Shows (a) the results of luminescence from the luciferase experiments of Example 2 of 7 days-old seedlings of the ABA-inducible reporter line pMAPKKK18-LUC+ measured 6 hours after the treatment of said seedlings with 2.5 ^M of compounds (Ia)- (In), (Ip), opabactin (OP) and control; (b) the results of luminescence from the luciferase experiments of Example 2 of 7 days-old seedlings of the ABA-inducible reporter line pMAPKKK18-LUC+ measured 6 hours after the treatment of said seedlings with 0.5 ^M and 2.5 ^M of cyanabactin (CB), compound (Ic), compound (It), ABA and control, and (c) the in vivo activity of compounds CB, compound (Ic), compound (It), ABA and control on seedling establishment of Arabidopsis seeds treated with varying concentrations.

[0014] Fig. 3 shows RNAseq results showing expression levels of different ABA- responsive genes after treating Arabidopsis seedlings with 2.5 ^M ABA, opabactin OP, (Ic) or Control.

[0015] Fig. 4 shows the crystal structure of the ternary complex CsPYL1-(lc)-dNHAB1 (top) and its comparison to the structure of the PYL10 receptor bound to the pan-agonist 3CB (structure obtained from Protein Data Bank reference number: 6NWC) (bottom).

[0016] Fig. 5 shows the germination, expressed as a percentage of tomato seeds untreated (diamond symbols) or treated with ABA (square symbols) and (Ic) (circular symbols) at a concentration of 0.5 ^M.

[0017] Fig.6 shows the evolution of stomatal conductance measured by IRGA according to Example 2, expressed in mol / m2s of tomato leaves treated with 10 ^M ABA (square symbols ), (Ic) (circular symbols) or 0.1% dimethylsulfoxide (diamond symbols) as control at different points in time following the treatment: 1 hour, 24 hours, 48 hours, 72 hours, 96 hours and 120 hours.

[0018] Fig. 7 shows the temperature difference according to Example 2 between leaves of tomato plants 24 hours after being sprayed with 50 ^M ABA or (Ic) and plants treated with 0.1 % dimethylsulfoxide as control.

[0019] Fig. 8 shows the expression levels of ABA-responsive genes SILEA and SIRAB18 according to Example 26 hours after treating tomato plants with 10 ^M ABA, (Ic) or 0.1 % dimethylsulfoxide as control determined by qRT-PCR.

[0020] Fig. 9 shows (a) Infra-red images of wheat plants after being sprayed with 50 ^M ABA, (Ic) or 0.1 % DMSO as control according to Example 2. (b) Temperature of the leaves of the plants used in (a) according to Example 2. (c) Expression level of the TaAOS ABA-responsive gene in plants treated with 50 ^M ABA, (Ic) or 0.1 % DMSO as control determined by qRT-PCR according to Example 2; (d) Pictures of plants treated with ABA, (Ic) or 0.1 % DMSO as control according to Example 2 after a drought period of 7 days of water deprivation, plants were re-watered, and stress recovery images were acquired after 3 days.

[0021] Fig. 10 shows (a) scheme of measurement of resistance of maize to drought of Example 2, giving rise to two kinds of maize plants: well-watered and drought; (b) evolution of stomatal conductance measured by IRGA according to Example 2, expressed in mol / m2s of well watered maize plants treated with 50 ^M ABA (square symbols), (Ic) (circular symbols) or 0.1% dimethylsulfoxide as control (diamond symbols) at different points in time following the treatment: 1 hour, 24 hours, 48 hours, 72 hours, 96 hours, 120 hours, 144 hours and 168 hours; (c) evolution of photosynthetic activity measured by IRGA according to Example 2, expressed in mmol CO2 / m2s of maize plants exposed to drought and treated with 50 ^M ABA (square symbols), (Ic) (circular symbols) or 0.1% dimethylsulfoxide (diamond symbols) as control at different points in time following the treatment: 1 hour, 24 hours, 48 hours, 72 hours, 96 hours, 120 hours, 144 hours and 168 hours; (d) evolution of soil water content measured by TEROS 12 sensor, according to Example 2 expressed in m3 / m3of maize plants exposed to drought and treated with 50 ^M ABA (square symbols), (Ic) (circular symbols) or 0.1% dimethylsulfoxide (diamond symbols) as control at different points in time following the treatment: from 2 to 7 days post-treatment.DETAILED DESCRIPTION

[0022] All terms as used herein in this application, unless otherwise stated, shall be understood in their ordinary meaning as known in the art. Other more specific definitions for certain terms as used in the present application are as set forth below and are intended to apply uniformly throughout the specification and claims unless an otherwise expressly set out definition provides a broader definition.

[0023] For the purposes of the invention, any ranges given include both the lower and the upper end-points of the range. Ranges given, such as temperatures, times, molar ratio, volume ratio and the like, should be considered approximate (i.e. with a 5% margin of variation around indicated point), unless specifically stated.

[0024] In the context of the present invention, the term “abiotic stress” refers to a condition of a plant exposed to adverse environmental conditions that are non-living or non-biological in nature, and are susceptible of negatively impacting the growth, development, and productivity of said plant. Such environmental conditions causing abiotic stress in a plant include, in a non-limiting way, drought, excess salinity of soil or irrigation water, extreme temperatures (heat stress or cold stress), acidic or alkaline soil (pH stress). In preferred embodiments of the present invention, the term “abiotic stress” refers to a condition susceptible of being prevented or mitigated by activation of ABA receptors in the plant. In further embodiments of the present invention, the term “abiotic stress” refers to one or more of drought stress, osmotic stress, stress caused by excess salinity and / or extreme temperatures. Thus, the “resistance to abiotic stress” encompasses resistance to any of the conditions listed above, such as drought or osmotic stress.

[0025] In the context of the present invention, the term “salt”, when referring to a specific compound, refers to salts of the compounds as described herein that are derived from suitable inorganic and organic acids and bases. Said acids and basis are preferablyagrochemically acceptable. Examples of salts of a basic group include those formed withinorganic acids such as hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid and perchloric acid or with organic acids such as acetic acid, oxalic acid, maleic acid, tartaric acid, citric acid, succinic acid or malonic acid or by using other methods used in the art such as ion exchange or protonation of the base with an adequate acid. Further salts include adipate, alginate, ascorbate, aspartate, benzenesulfonate, benzoate, bisulfate, borate, butyrate, camphorate, camphorsulfonate, citrate, cyclopentanepropionate, digluconate, dodecylsulfate, ethanesulfonate, formate, fumarate, glucoheptonate, glycerophosphate, gluconate, hemisulfate, heptanoate, hexanoate, hydroiodide, 2- hydroxy-ethanesulfonate, lactobionate, lactate, laurate, lauryl sulfate, malate, maleate, malonate, methanesulfonate, 2-naphthalenesulfonate, nicotinate, nitrate, oleate, oxalate, palmitate, palmoate, pectinate, persulfate, 3- phenylpropionate, phosphate, pivalate, propionate, stearate, succinate, sulfate, tartrate, thiocyanate, p-toluenesulfonate, undecanoate, valerate salts, and the like. Examples of salts of an acidic group include those formed with appropriate base, such as an inorganic base including hydroxide salts of alkali metal, alkaline earth metal, ammonium or organic bases such as hydroxide salts of N+(C1-C4alkyl)4 or compounds of formula N((C1- C4alkyl)3.

[0026] In the context of the present invention, the term “solvate”, when referring to a specific compound, refers to a complex formed by combination of one or more solvent molecules with one or more molecules or ionized forms (e.g. salts) of said compound. Suitable solvents are those comprising hydrogen bond donor or acceptor groups. Suitable solvents for forming solvates include, but are not limited to, water, methanol, ethanol, iso-propanol, acetone, acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, tetrahydrofuran. Preferably, said solvent is agrochemically acceptable. In general, the solvated forms are equivalent to unsolvated forms and are encompassed within the scope of the present disclosure. Also, certain compounds of the present disclosure may exist in multiple crystalline or amorphous forms. In general, all physical forms are equivalent for the uses contemplated by the present disclosure and are intended to be within the scope of the present disclosure.

[0027] In the context of the present invention, the term “stereoisomer”, when referring to a specific compound, refer to compounds that exist in different stereoisomeric forms if they possess one or more asymmetric centres or a double bond with asymmetric substitution and, therefore, may be produced as individual stereoisomers or as mixtures. Stereoisomers include enantiomers and diastereomers. Stereoisomers that are non- superimposable mirror images of each other are termed “enantiomers”. A chiral compound may exist as either individual enantiomers or as a mixture thereof. Unless otherwise indicated, the description is intended to include individual stereoisomers as well as mixtures. The methods for the determination of stereochemistry and the separation of stereoisomers are well-known in the art (see discussion in Chapter 4 of Advanced Organic Chemistry, 6th edition J. March, John Wiley and Sons, New York, 2007).

[0028] In the context of the present invention, a compound is a “deuterated analogue” of a specific compound disclosed herein when deuterium atoms are placed in substitution of one or more hydrogen atoms in said specific compound. The deuterated analogue of the disclosure may be a fully or partially deuterated analogue. Unless otherwise stated, when a position is designated specifically as “H” or “hydrogen”, the position is understood to have hydrogen at its natural abundance isotopic composition or its isotopes, such as deuterium (D) or tritium (3H). Further, substitution with heavier isotopes such as deuterium (i.e.,2H or D) may afford certain advantages resulting from greater metabolic stability and hence may be preferred in some circumstances. Isotopically labelled compounds of the present disclosure may generally be prepared by following procedures analogous to those described in the Schemes and in the Examples herein below, by substituting a non-isotopically labelled reagent for an isotopically labelled reagent.

[0029] In the context of the present invention, the term “alkyl” refers to a linear or branched saturated hydrocarbon chain having the number of carbon atoms specified herein. In preferred embodiments, the alkyl groups in the compounds of the present invention are (C1-C6)alkyl groups, including, but not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl and hexyl. In further preferred embodiments, the alkyl groups in the compounds of the present invention are (C1-C3)alkyl groups, including, but not limited to, methyl, ethyl, propyl, and isopropyl. When an alkyl group is optionally substituted with one or more fluorine atoms, it is intended to encompass the embodiment wherein all hydrogen atoms are replaced by fluorine atoms. Such groups are also referred to in the art as perfluoroalkyl groups. In the context of the present invention, particularly relevant perfluoroalkyl groups include perfluoromethyl, perfluoroethyl and perfluoropropyl.

[0030] In the context of the present invention, the term “cycloalkyl” refers to a cyclic saturated hydrocarbon group having the number of carbon atoms specified herein. In preferred embodiments, the cycloalkyl groups in the compounds of the present invention are (C3-C6)alkyl groups, including, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. In further preferred embodiments, the alkyl groups in the compounds of the present invention are (C3-C4)alkyl groups, including cyclopropyl and cyclobutyl.

[0031] In the context of the present invention, the term “halogen” or “halo” refers to a halogen group such as fluoro-, chloro-, bromo- or iodo-. In preferred embodiments, said halo group is a chloro- or a bromo-.

[0032] In the context of the present invention, the term “carrier”, when referring to a composition comprising an active ingredient, refers to a material with which said active ingredient is formulated to facilitate application to a surface, or to facilitate storage, transport or handling of said composition. Such carrier may be solid or liquid.

[0033] As defined above, a first aspect of the invention relates to a compound of formula (I) as defined above.

[0034] In a preferred embodiment, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein each of R1 and R2 is independently selected from the group consisting of hydrogen, a linear or branched (C1-C3)alkyl group and a (C3-C4)cycloalkyl group and provided that at least one of R1 and R2 is other than hydrogen.

[0035] In a further preferred embodiment, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein each of R1 and R2 is independently selected from the group consisting of hydrogen, ethyl, propyl, isopropyl and a cyclopropyl group and provided that at least one of R1 and R2 is other than hydrogen.

[0036] In a further preferred embodiment, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein one of R1 and R2 is hydrogen. Preferably, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein one of R1 and R2 is hydrogen and the other group of R1 and R2 is selected from the group consisting of a linear or branched (C1-C3)alkyl group and a (C3-C4)cycloalkyl group.

[0037] In a further preferred embodiment, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein one of R1 and R2 is hydrogen and the other group of R1 and R2 is selected from the group consisting of ethyl, propyl, isopropyl and a cyclopropyl group.

[0038] In further embodiments of the invention, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein R1 and R2 are each independently selected from the group consisting of ethyl, propyl, isopropyl and a cyclopropyl group.

[0039] In further more preferred embodiments of the invention, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein R1 and R2 are the same group that is selected from the group consisting of ethyl, propyl, isopropyl and a cyclopropyl group.

[0040] In further embodiments, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein Z is a radical of formula (A).

[0041] In further embodiments, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein Z is a radical of formula (A) wherein Y is selected from the group consisting of CHR3 and C(R3)2; preferably, Y is a CHR3 group.

[0042] In further embodiments, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein, in the radicals of formula (A) and (B), each R3 is independently a (C1-C3)alkyl that is optionally substituted with one or more fluorine atoms.

[0043] In further embodiments, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein, in the radicals of formula (A) and (B), each R3 is independently selected from the group consisting of hydrogen, fluoro, (C1-C3)alkyl and (C1-C3)perfluoroalkyl; preferably each R3 is independently selected from the group consisting (C1-C3)alkyl and (C1- C3)perfluoroalkyl.

[0044] In further embodiments, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein, in the radicals of formula (A) and (B), each R3 is independently selected from the group consisting of methyl and trifluoromethyl.

[0045] In further embodiments, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein in the radicals of formula (A) and (B), each R3 is a (C1-C6) alkyl group, preferably each R3 is a (C1-C3) alkyl group; more preferably, each R3 is a methyl group.

[0046] In other embodiments, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein in the radicals of formula (A) and (B), each R3 is a (C1-C6) perfluoroalkyl group, preferably each R3 is a (C1-C3) perfluoroalkyl group; more preferably, each R3 is a trifluoromethyl group.

[0047] In further embodiments, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein Z is a radical of formula (A) wherein Y is a CHR3 group wherein R3 is selected from the group consisting of hydrogen, (C1-C6)alkyl and (C1-C6)perfluoroalkyl.

[0048] In further embodiments, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein Z is a radical of formula (A) wherein Y is a CHR3 group wherein R3 is selected from the group consisting of hydrogen, (C1-C3)alkyl and (C1-C3)perfluoroalkyl.

[0049] In further embodiments, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein Z is a radical of formula (A) wherein Y is a CHR3 group wherein R3 is selected from the group consisting of hydrogen, methyl and trifluoromethyl.

[0050] In further embodiments, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein Z is a radical of formula (A) wherein Y is a NR3 group wherein R3 is selected from the group consisting of (C1-C6)alkyl and (C1-C6)perfluoroalkyl.

[0051] In further embodiments, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein Z is a radical of formula (A) wherein Y is a NR3 group wherein R3 is selected from the group consisting of (C1-C3)alkyl and (C1-C3)perfluoroalkyl.

[0052] In further embodiments, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein Z is a radical of formula (A) wherein Y is a NR3 group wherein R3 is selected from the group consisting of methyl and trifluoromethyl.

[0053] In further embodiments, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein Z is a radical of formula (A) wherein Y is O.

[0054] In further embodiments, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein Z is a radical of formula (B) wherein R3 is selected from the group consisting of hydrogen, (C1-C6)alkyl and (C1-C6)perfluoroalkyl; preferably R3 is selected from the group consisting of hydrogen, (C1-C3)alkyl and (C1-C3)perfluoroalkyl, and even more preferably R3 is selected from the group consisting of hydrogen, methyl and trifluoromethyl.

[0055] In further embodiments, the first aspect of the invention relates to a compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein Z is a radical of formula (B) wherein R3 is a methyl group.

[0056] The embodiments defined above defining different alternatives for each of the R1, R2 and R3 groups may be combined to form compounds of formula (I) according to the first aspect of the invention wherein R1, R2 and R3 are defined in said combined embodiments.

[0057] In further preferred embodiments, the first aspect of the invention relates to a compound of formula (I) that is selected from the group consisting of the compounds of formulae or salts, solvates, stereoisomers or deuterated analogues thereof.

[0058] The compound of formula (Ia) is a compound of formula (I) wherein R1 is ethyl, R2 is hydrogen, Z is a radical of formula (A) wherein Y is CHR3 and R3 is methyl. The compound of formula (Ib) is a compound of formula (I) wherein R1 is propyl, R2 is hydrogen, Z is a radical of formula (A) wherein Y is CHR3 and R3 is methyl. The compound of formula (Ic) is a compound of formula (I) wherein R1 is cyclopropyl, R2 is hydrogen, Z is a radical of formula (A) wherein Y is CHR3 and R3 is methyl. The compound of formula (Id) is a compound of formula (I) wherein R1 is cyclopropyl, R2 is cyclopropyl, Z is a radical of formula (A) wherein Y is CHR3 and R3 is methyl. The compound of formula (Ie) is a compound of formula (I) wherein R1 is isopropyl, R2 is isopropyl, Z is a radical of formula (A) wherein Y is CHR3 and R3 is methyl. The compound of formula (If) is a compound of formula (I) wherein R1 is ethyl, R2 is ethyl, Z is a radical of formula (A) wherein Y is CHR3 and R3 is methyl. The compound of formula (Ig) is a compound of formula (I) wherein R1 is propyl, R2 is propyl, Z is a radical of formula (A) wherein Y is CHR3 and R3 is methyl. The compound of formula (Ih) is a compound of formula (I) wherein R1 is ethyl, R2 is hydrogen, Z is a radical of formula (A) wherein Y is CHR3 and R3 is trifluoromethyl. The compound of formula (Ii) is a compound of formula (I) wherein R1 is isopropyl, R2 is hydrogen, Z is a radical of formula (A) wherein Y is CHR3 and R3 is trifluoromethyl. The compound of formula (Ij) is a compound of formula (I) wherein R1 is cyclopropyl, R2 is hydrogen, Z is a radical of formula (A) wherein Y is CHR3 and R3 is trifluoromethyl. The compound of formula (Ik) is a compound of formula (I) wherein R1 is cyclopropyl, R2 is cyclopropyl, Z is a radical of formula (A) wherein Y is CHR3 and R3 is trifluoromethyl. The compound of formula (Il) is a compound of formula (I) wherein R1 is isopropyl, R2 is isopropyl, Z is a radical of formula (A) wherein Y is CHR3 and R3 is trifluoromethyl. The compound of formula (Im) is a compound of formula (I) wherein R1 is ethyl, R2 is ethyl, Z is a radical of formula (A) wherein Y is CHR3 and R3 is trifluoromethyl. The compound of formula (In) is a compound of formula (I) wherein R1 is propyl, R2 is propyl, Z is a radical of formula (A) wherein Y is CHR3 and R3 is trifluoromethyl. The compound of formula (Io) is a compound of formula (I) wherein R1 is isopropyl, R2 is hydrogen, Z is a radical of formula (A) wherein Y is CHR3 and R3 is methyl. The compound of formula (Ip) is a compound of formula (I) wherein R1 is isopropyl, R2 is hydrogen, Z is a radical of formula (A) wherein Y is CHR3 and R3 is trifluoromethyl. The compound of formula (Iq) is a compound of formula (I) wherein R1 is cyclopropyl, R2 is hydrogen, Z is a radical of formula (A) wherein Y is CHR3 and R3 is hydrogen. The compound of formula (Ir) is a compound of formula (I) wherein R1 is cyclopropyl, R2 is hydrogen, Z is a radical of formula (A) wherein Y is O. The compound of formula (Is) is a compound of formula (I) wherein R1 is cyclopropyl, R2 is hydrogen, Z is a radical of formula (A) wherein Y is NR3 and R3 is methyl. The compound of formula (It) is a compound of formula (I) wherein R1 is cyclopropyl, R2 is hydrogen, Z is a radical of formula (B) wherein R3 is methyl.

[0059] In further preferred embodiments, the first aspect of the invention relates to a compound of formula (I) that is selected from the group consisting of the compounds of formulae (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ih), (Ij), (Ik), (Il), (Im), (In), (Ip) and (It) as defined above or salts, solvates, stereoisomers or deuterated analogues thereof.

[0060] In further preferred embodiments, the first aspect of the invention relates to a compound of formula (I) that is selected from the group consisting of the compounds of formulae (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ih), (Ij), (Ik), (Il), (Im), (In) and (Ip) as defined above or salts, solvates, stereoisomers or deuterated analogues thereof.

[0061] In further preferred embodiments, the first aspect of the invention relates to a compound of formula (I) that is selected from the compounds of formulae (Ia), (Ib), (Ic), (If), (Ih), (Ij), (Ik), (Ip) and (It) or salts, solvates, stereoisomers or deuterated analogues thereof.

[0062] In further preferred embodiments, the first aspect of the invention relates to a compound of formula (I) that is selected from the compounds of formulae (Ia), (Ib), (Ic), (If), (Ih), (Ij), (Ik) and (Ip) or salts, solvates, stereoisomers or deuterated analogues thereof.

[0063] In further preferred embodiments, the first aspect of the invention relates to a compound of formula (I) that is selected from the compounds of formulae (Ia), (Ib), (Ic); (Ij) and (It) or salts, solvates, stereoisomers or deuterated analogues thereof. The inventors found that these compounds were particularly active agonists of ABA receptors.

[0064] In further preferred embodiments, the first aspect of the invention relates to a compound of formula (I) that is selected from the compounds of formulae (Ia), (Ib), (Ic) and (Ij) or salts, solvates, stereoisomers or deuterated analogues thereof. The inventors found that these compounds were particularly active agonists of ABA receptors.

[0065] In further preferred embodiments, the first aspect of the invention relates to a compound of formula (I) that is the compound of formula (It) or the compound of formula (Ic) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof.

[0066] In further preferred embodiments, the first aspect of the invention relates to a compound of formula (I) that is the compound of formula (Ic) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof.

[0067] In further preferred embodiments, the first aspect of the invention relates to a compound of formula (I) having an IC50 for the agonism of PYL1 receptors of maize of no more than 80 nM; preferably of no more than 50, 40, 30, 25, 20, 15, 10 or 5 nM. In further preferred embodiments, the first aspect of the invention relates to a compound of formula (I) having an IC50 for the agonism of PYL2 receptors of maize of no more than 125 nM; preferably of no more than 100, 75, 50, 40, 30, 25, 20, 15, 10, 8, 5, or 3 nM. In further preferred embodiments, the first aspect of the invention relates to a compound of formula (I) having an IC50 for the agonism of PYL3 receptors of maize of no more than 45 nM; preferably of no more than 40, 35, 30 or 25 nM. In further preferred embodiments, the first aspect of the invention relates to a compound of formula (I) having an IC50 for the agonism of PYL13 receptors of maize of no more than 13 nM; preferably of no more than 10, 9, 8 or 7 nM.

[0068] In further preferred embodiments, the first aspect of the invention relates to a compound of formula (I) having an IC50 for the agonism of PYL1 receptors of Arabidopsis of no more than 115 nM; preferably of no more than 100, 75, 50, 40, 30, 25, 20, 15, 10 or 8 nM.

[0069] In further preferred embodiments, the first aspect of the invention relates to a compound of formula (I) having an IC50 for inhibiting seed germination of no more than 300 nM; preferably of no more than 250, 200, 150, 100, 50, 40, 35, 30, 25, 20, 15, 14,13, 12, 11, 10, 9 or 8 nM.

[0070] A process for the preparation of a compound of formula (I) is also part of the invention.

[0071] As defined above, the second aspect of the invention relates to a process for the preparation of a compound of formula (I) as defined in the first aspect of the invention comprising the step of contacting a compound of formula (II) with a compound of formula (III) in conditions sufficient for the formation of the compound of formula (I) (II) (III) wherein X is a halogen group and R1, R2 and Z are as defined in the first aspect of the invention.

[0072] Preferably, in the compounds of formula (II), R1 and R2 are as defined in any of the embodiments of the first aspect of the invention defining said groups. Also, in the compounds of formula (III), Z is as defined in any of the embodiments of the first aspect of the invention defining said group.

[0073] Also preferably, in the compound of formula (III), X is a chloro group.

[0074] In preferred embodiments of the second aspect of the invention, the step of contacting a compound of formula (II) with a compound of formula (III) is carried out in the presence of a base. Suitable bases for such step are known in the art and will be easily recognized by the skilled person. Those include, for instance, carbonate salts of alkaline or alkaline earth metals and tertiary amines, such as the compounds of formula N[(C1-C6)alkyl]3, for instance trimethylamine and diisopropylethylamine. The base is preferably diisopropylethylamine. The base is preferably in an amount of at least 1 mole of base per mole of compound of formula (III); preferably it is of between 1 and 5 moles of base per mole of compound of formula (III); more preferably it is of about 3 moles of base per mole of compound of formula (III).

[0075] Suitable solvents for carrying out said step are those wherein the compounds of formulae (II) and (III), and eventually, the base, are soluble. Such solvent is preferably a polar aprotic solvent, such as N-methylpyrrolidinone (NMP), N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), and dimethylsulfoxide (DMSO). Preferably, the solvent is N,N-dimethylformamide (DMF).

[0076] In preferred embodiments of the second aspect of the invention, the step of contacting a compound of formula (II) with a compound of formula (III) is one wherein the molar ratio of the compound of formula (II) to compound of formula (III) is comprised between 1:1.2 to 1.2:1; preferably, it is of about 1:1.

[0077] In preferred embodiments of the second aspect of the invention, the step of contacting a compound of formula (II) with a compound of formula (III) is carried out at a temperature of between 15 ºC and 30 ºC; more preferably at a temperature of about 25 ºC, i.e. room temperature.

[0078] In further embodiments, the process of the second aspect of the invention further comprises the previous step of preparing a compound of formula (II) as defined above by contacting a compound of formula (IV) with hydrazine in conditions sufficient for the formation of the compound of formula (II) wherein R1 and R2 are as defined in any of the embodiments of the first aspect of the invention.

[0079] In preferred embodiments, said hydrazine is hydrazine hydrate.

[0080] As will be acknowledged by the skilled person, this transformation is also called the Ing-Manske procedure, which is well established in the art for the Gabriel reaction – such that the skilled person will readily identify suitable conditions for implementing this process step. In particular, this step is preferably carried out in an alcoholic solvent, such as methanol, ethanol or isopropanol; preferably ethanol. Also preferably, this step is carried out under reflux conditions of said solvent. The amount of hydrazine suitable for this reaction is of at least 1 mole of hydrazine per mole of compound of formula (IV); preferably of between 1 and 10 moles of hydrazine per mole of compound of formula (IV); more preferably of about 6 moles of hydrazine per mole of compound of formula (IV).

[0081] In further embodiments, the process of the second aspect of the invention further comprises the previous step of preparing a compound of formula (IV) as defined above by Suzuki coupling from a compound of formula (Va) or (Vb) and a compound of formula R4-B(OH)2 or R4-BF3K; wherein R4 is selected from a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a (C3- C6)cycloalkenyl and a (C3-C6)cycloalkyl group.

[0082] Alternatively to a compound of formula R4-B(OH)2, or R4-BF3K, a compound of formula (C) may be used wherein R4 is selected from a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a (C3-C6)cycloalkenyl and a (C3-C6)cycloalkyl group; the dashed bond represents the presence or absence of a covalent bond; when the dashed bond represents the absence of a covalent bond each of R4’ and R4’’ is independently selected from the group consisting of hydrogen and (C1-C6)alkyl group or, alternatively, R4’ and R4’’ together with the atoms to which they are attached form a 6 to 8-membered saturated or unsaturated ring, the members of said ring being selected from C, CH, CH2, B and O and said ring being further optionally substituted at any available position with a (C1-C6)alkyl group; and, when the dashed bond represents the presence of a covalent bond each of R4’ and R4’’ is independently hydrogen or a (C1- C6)alkyl group; or, alternatively, R4’ and R4’’ together with the atoms to which they are attached form a 3 to 8-membered aromatic, saturated or unsaturated ring, the members of said ring being selected from C, CH and CH2, and said ring being further optionally substituted at any available position with a (C1-C6)alkyl group. Preferred compounds of formula (C) include boronate esters of the kind pinacol boronate, neopentyl boronate and catechol boronate.

[0083] As will be obvious to the skilled person, the Suzuki coupling of (Va) with a compound of formula R4-B(OH)2 or R4-BF3K or a compound of formula (C) as defined above produces a compound of formula (IV’) wherein one of R1’ and R2’ is hydrogen and the other group of R1’ and R2’ is selected from a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a (C3-C6)cycloalkenyl and a (C3-C6)cycloalkyl group. Also, the Suzuki coupling of (Vb) with a compound of formula R4-B(OH)2 or R4-BF3K or a compound of formula (C) as defined above produces a compound of formula (IV’) wherein R1’ and R2’ are the same group and are selected from a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a (C3-C6)cycloalkenyl and a (C3-C6)cycloalkyl group.

[0084] A compound of formula (IV’) as defined above wherein R1’ and R2’ are each independently selected from the group consisting of a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a (C3-C6)cycloalkenyl and a (C3- C6)cycloalkyl group, may be obtained by: (i) contacting a compound of formula (Va) with a compound of formula R4-B(OH)2 or of formula R4-BF3K or a compound of formula (C) as defined above in conditions sufficient for the formation of a compound of formula (IV) wherein R4 is selected from a linear or branched (C1-C6)alkyl group, a linear or branched (C2- C6)alkenyl group, a (C3-C6)cycloalkenyl and a (C3-C6)cycloalkyl group; (ii) contacting the product of step (i) with a bromination agent such as N- bromosuccinimide so as to produce a compound of formula (VI) wherein R4 is selected from a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a (C3-C6)cycloalkenyl and a (C3-C6)cycloalkyl group; and (iii) contacting the product of step (ii) ) with a compound of formula R4-B(OH)2 or of formula R4-BF3K or a compound of formula (C) as defined above in conditions sufficient for the formation of a compound of formula (IV) wherein R4 is selected from a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a (C3-C6)cycloalkenyl and a (C3-C6)cycloalkyl group. The compound of formula (IV’) thus obtained may be used in further steps using the compound of formula (IV) as starting material for the preparation of a compound of formula (I).

[0085] In each of the three alternatives depicted above, when R4 is one of a linear or branched (C2-C6)alkenyl group or a (C3-C6)cycloalkenyl, the process of the second aspect of the invention further comprises the step of converting said linear or branched (C2-C6)alkenyl group or a (C3-C6)cycloalkenyl in a linear or branched (C2-C6)alkyl group or a (C3-C6)cycloalkyl group, respectively; preferably, this transformation is carried out by catalytic hydrogenation using for instance palladium as catalyst under an atmosphere of hydrogen. The solvent of said hydrogenation step is preferably a polar protic solvent, such as an alcoholic solvent, eventually in admixture with water. This allows producing a compound of formula (IV) from the compound of formula (IV’).

[0086] Suzuki coupling is a well-established reaction in the art, such that the skilled person will readily identify suitable conditions for converting the compounds of formulae (Va) and (Vb) in a compound of formula (IV’) as defined above. Such conditions include the presence of a palladium(0) catalyst used in a catalytically effective amount, a ligand and a base.

[0087] Said palladium(0) catalyst is preferably prepared in situ by reaction of a palladium(II) salt, such as palladium(II) acetate, with a phosphine ligand, such as tricyclohexylphosphine or RuPhos (Dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2- yl)phosphine). Other combinations of palladium salts and phosphine compounds suitable for the Suzuki reaction are known in the art and will become apparent to the skilled person upon reduction to practice of the invention.

[0088] Suitable bases for the Suzuki reaction are also known in the art and will become apparent to the skilled person upon reduction to practice of the invention. Those include, for instance, alkali or alkali earth metal salts of carbonate or phosphate, such as for instance potassium phosphate tribasic.

[0089] In further embodiments, when the compound of formula (Va) or (Vb) is contacted with a compound of formula R4-BF3K, the catalyst is preferably formed by reaction of palladium(II) acetate with RuPhos. The reaction preferably takes place at a temperature comprised between 80 ºC and 120 ºC; more preferably of about 100 ºC.

[0090] In other embodiments, when the compound of formula (Va) or (Vb) is contacted with a compound of formula R4-B(OH)2, the catalyst is preferably formed by reaction of palladium(II) acetate with tricyclohexylphosphine. The reaction preferably takes place at a temperature comprised between 80 ºC and 120 ºC; more preferably of about 100 ºC.

[0091] As will be obvious to the skilled person, when said step comprises the reaction of compound (Va) or (VI) comprising one bromine atom in its molecular formula, the molar amount of the compound of formula R4-B(OH)2 or of formula R4-BF3K or of formula (C) is preferably of at least 1 mole of the compound of formula R4-B(OH)2 or of formula R4- BF3K or of formula (C) per mole of the compound of formula (Va) or (VI); more preferably of about 1.5 mole of the compound of formula R4-B(OH)2 or of formula R4-BF3K per mole of the compound of formula (Va) or (VI).

[0092] Similarly, when said step comprises the reaction of compound (Vb) comprising two bromine atoms in its molecular formula, the molar amount of the compound of formula R4-B(OH)2 or of formula R4-BF3K or of formula (C) is preferably of at least 2 moles of the compound of formula R4-B(OH)2 or of formula R4-BF3K or of formula (C) per mole of the compound of formula (Vb); more preferably of about 3 moles of the compound of formula R4-B(OH)2 or of formula R4-BF3K or of formula (C) per mole of the compound of formula (Vb).This procedure allows preparing a compound of formula (IV’) wherein R1’ and R2’ are the same group.

[0093] In further embodiments, the process of the second aspect of the invention further comprises the previous step of preparing a compound of formula (Va) or (Vb) said process comprising the step of contacting 4-((1,3-dioxoisoindolin-2- yl)methyl)benzonitrile with a bromination agent such as N-bromosuccinimide in conditions sufficient for the formation of the compound of formula (Va) or (Vb).

[0094] Preferably, when said step produces the compound of formula (Va) the molar amount of N-bromosuccinimide is of between 1 and 1.2 mole of N-bromosuccinimide per mole of 4-((1,3-dioxoisoindolin-2-yl)methyl)benzonitrile; or, alternatively, when said step produces the compound of formula (Vb) the molar amount of N-bromosuccinimide is of at least 2 moles of N-bromosuccinimide per mole of 4-((1,3-dioxoisoindolin-2- yl)methyl)benzonitrile.

[0095] The previous step of preparing a compound of formula (Va) or (Vb) comprising the step of contacting 4-((1,3-dioxoisoindolin-2-yl)methyl)benzonitrile with a bromination agent such as N-bromosuccinimide is preferably carried out in the presence of palladium(II) catalyst such as palladium(II) acetate used in a catalytically effective amount. Even more preferably, said step is carried out in the presence of a catalytically effective amount of an acid, such as an organic acid, for instance camphor sulfonic acid.

[0096] In further embodiments, the process of the second aspect of the invention further comprises the previous step of preparing 4-((1,3-dioxoisoindolin-2- yl)methyl)benzonitrile, said step comprising contacting 4-(halomethyl)benzonitrile with an alkaline phthalimide salt in conditions sufficient for the formation of 4-((1,3- dioxoisoindolin-2-yl)methyl)benzonitrile.

[0097] In preferred embodiments, 4-(halomethyl)benzonitrile refers to 4- (chloromethyl)benzonitrile or 4-(bromomethyl)benzonitrile or 4-(iodomethyl)benzonitrile; preferably to 4-(bromomethyl)benzonitrile.

[0098] Said alkaline phthalimide salt is preferably potassium phthalimide. The molar amount of the alkaline phthalimide salt is preferably of about 1 mole of alkaline phthalimide salt per mole of 4-(bromomethyl)benzonitrile.

[0099] This reaction step is preferably carried out in a polar aprotic solvent, such as acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide. The temperature of said reaction step is preferably of about 90 ºC. The second aspect of the invention thus relates in preferred embodiments to a process for the preparation of a compound of formula (I) which comprises the following steps:

[0100] As mentioned above, the third aspect of the invention relates to an agrochemical composition comprising the compound of formula (I) as defined in the first aspect of the invention or a salt, a solvate, a stereoisomer or a deuterated analogue thereof, and an agrochemically acceptable carrier.

[0101] In preferred embodiments of the third aspect of the invention, the compound of formula (I) is as defined in any embodiment describe above for the first aspect of the invention.

[0102] In further embodiments of the third aspect of the invention, said agrochemical composition is in a form suitable for an administration mode to a plant selected from the group consisting of spraying, sprinkling, soil administration (e.g. plowing, tilling, mixing, drenches), seed coating, admixture with irrigation water, aerosols, foggers, granules, pellets and trunk injection. In further embodiments of the third aspect of the invention, said agrochemical composition is in a form suitable for spraying; preferably it is in a form of a sprayable liquid.

[0103] In particular embodiments, said agrochemical composition is in the liquid form.

[0104] In other particular embodiments, said agrochemical composition is in the solid form. Such solid forms may further be diluted in a solvent system, such as water, at an effective concentration of the compound of formula (I), prior to use.

[0105] Suitable carriers for agrochemical composition are known in the art and will become apparent to the skilled person upon reduction to practice of the invention. Any of the carriers commonly used in the art of formulating agrochemical compositions (e.g. herbicidal, fungicidal or pesticidal) may be used in the compositions of the third aspect of the invention.

[0106] In particular embodiments of the third aspect of the invention, the agrochemical composition comprises a solid carrier selected from the group consisting of natural and synthetic clays and silicates, for example natural silicas such as diatomaceous earths; magnesium silicates, for example talcs; magnesium aluminium silicates, for example attapulgites and vermiculites; aluminium silicates, for example kaolinites, montmorillonites and micas; calcium carbonate; calcium sulfate; ammonium sulfate; synthetic hydrated silicon oxides and synthetic calcium or aluminium silicates; elements, for example carbon and sulfur; natural and synthetic resins, for example coumarone resins, polyvinyl chloride, and styrene polymers and copolymers; solid polychlorophenols; bitumen; waxes; and solid fertilisers, for example superphosphates.

[0107] In other particular embodiments of the third aspect of the invention, the agrochemical composition comprises a liquid carrier selected from the group consistingof water; alcohols, for example isopropanol and glycols; ketones, for example acetone,methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; ethers; aromatic or araliphatic hydrocarbons, for example benzene, toluene and xylene; petroleum fractions, for example kerosene and light mineral oils; chlorinated hydrocarbons, for example carbon tetrachloride, perchloroethylene and trichloroethane. Mixtures of different liquids may be suitable. Said liquid composition may be formulated and transported in a concentrated form which is subsequently diluted by the user before application. The presence of small amounts of a carrier which is a surface-active agent facilitates this process of dilution. Further organic liquid carriers include liquid aliphatic hydrocarbons (e.g., pentane, hexane, heptane, nonane, decane and their analogs) and liquid aromatic hydrocarbons. Examples of other liquid hydrocarbons include oils produced by the distillation of coal and the distillation of various types and grades of petrochemical stocks, including kerosene oils which are obtained by fractional distillation of petroleum. Other petroleum oils include those generally referred to as agricultural spray oils (e.g., the so- called light and medium spray oils, consisting of middle fractions in the distillation of petroleum and which are only slightly volatile). Such oils, moreover, are generally paraffin oils and accordingly may be emulsified with water and an emulsifier, diluted to lower concentrations, and used as sprays. Tall oils, obtained from sulfate digestion of wood pulp, like the paraffin oils, may similarly be used. Other organic liquid carriers may include liquid terpene hydrocarbons and terpene alcohols such as alphapinene, dipentene, terpineol, and the like.

[0108] In certain embodiments of the third aspect of the invention, the agrochemical composition comprises an aqueous solvent. The term “aqueous solvent” refers herein to a solvent comprising at least 50% in volume of water. An aqueous solvent may thus encompass mixtures of water with liquid organic compounds that are miscible with water.

[0109] In some embodiments of the third aspect of the invention, the agrochemical composition comprises water as a solvent. In some embodiments of the third aspect of the invention, the agrochemical composition comprises a buffer. Said buffer may comprise, for instance, one of citric acid, phosphoric acid, potassium hydroxide, ammonium hydroxide or 3-(N-morpholimyl)propoanesulfonic acid (MES).

[0110] In some embodiments of the third aspect of the invention, the agrochemical composition comprises a wetting agent, such as one of alkylphenol ethoxylates, lakyl polyglycosides, polyoxyethylene sorbitan esters (e.g. tween20), alcohol ethoxylates or silweet.

[0111] In some embodiments of the third aspect of the invention, the agrochemical composition has a pH of between 3 and 10, more particularly of between 4 and 9, more particularly of between 5 and 8. In further embodiments of the third aspect of the invention, the agrochemical composition has a pH of about 5.7.

[0112] In addition, in certain embodiments, at least one carrier in a composition as described herein may be a surface-active agent. For example, the composition may comprise two carriers, one of which being a surface-active agent.

[0113] In said embodiments, the surface-active agent, which may be ionic or non-ionic, is selected from the group consisting of an emulsifying agent, a dispersing agent or a wetting agent. Suitable emulsifying, dispersing or wetting agents for agrochemical formulations are well known in the art and will become apparent to the skilled person upon reduction to practice of the invention. Those include, for instance, the sodium or calcium salts of polyacrylic acids and lignin sulfonic acids; the condensation product of fatty acids or aliphatic amines or amides containing at least 12 carbon atoms in their molecular formula with ethylene oxide and / or propylene oxide; fatty acid esters of glycerol, sorbitol, sucrose or pentaerythritol or condensates thereof with ethylene oxide and / or propylene oxide; condensation products of fatty alcohol or alkyl phenols, for example p-octylphenol or p-octylcresol, with ethylene oxide and / or propylene oxide or sulfates or sulfonate salts thereof; alkali or alkaline earth metal salts, preferably sodium salts, of sulfuric or sulfonic acid esters containing at least 10 carbon atoms in their molecular formula, for example sodium lauryl sulfate, sodium secondary alkyl sulfates, sodium salts of sulfonated castor oil, and sodium alkylaryl sulfonates such as dodecylbenzene sulfonate; and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide.

[0114] Also, further carrier agents are disclosed in Yusoff, S. N. M.; Kamari, A.; Aljafree, N. F. A. (2016). A review of materials used as carrier agents in pesticide formulations. International Journal of Environmental Science and Technology, 13(12), 2977–2994, in particular in Table 3 column 1, the content of which is incorporated herein by reference.

[0115] In other particular embodiments, the agrochemical composition of the third aspect of the invention is in a form selected from the group consisting of wettable powder, dust, granule, solution, emulsifiable concentrate, emulsion, suspension concentrate and aerosol. In certain embodiments, wettable powders comprise 25, 50 or 75% w / w of active ingredient and a solid inert carrier, 3-10% w / w of a dispersing agent and, where necessary, 0-10% w / w of stabiliser(s) and / or other additives such as penetrants or stickers. In certain embodiments, dusts are formulated as a dust concentrate having a similar composition to that of a wettable powder but without a dispersant. In certain embodiments, granules are prepared to have a size between 10 and 100 BS mesh (1.676 - 0.152 mm particle size), and may be manufactured by agglomeration or impregnation techniques. Preferably, granules comprise 0.5-75% w / w active ingredient and 0-10% w / w of additives such as stabilisers, surfactants, slow-release modifiers and binding agents. In certain embodiments, emulsifiable concentrates comprise, in addition to a solvent and, when necessary, a co-solvent, 10-50% w / v active ingredient, 2-20% w / v emulsifiers and 0-20% w / v of other additives such as stabilisers, penetrants and corrosion inhibitors. In other embodiments, suspension concentrates comprise 10-75% w / w active ingredient, 0.5- 15% w / w of dispersing agents, 0.1-10% w / w of suspending agents such as protective colloids and thixotropic agents, 0-10% w / w of other additives such as defoamers, corrosion inhibitors, stabilisers, penetrants and stickers, and water or an organic liquid in which the active ingredient is substantially insoluble. In further embodiments, aerosol formulations comprise the active ingredient, solvents, furthermore auxiliaries such as emulsifiers, perfume oils, if appropriate stabilisers, and, if required, propellants.

[0116] In other particular embodiments, the agrochemical composition of the third aspect of the invention further comprises a further agrochemically active compound, such as a fungicide, an herbicide, a pesticide, a nematicide, an insecticide, a plant activator, a synergist, an herbicide safener, a plant growth regulator, an insect repellant, an acaricide, a molluscicide, or a fertilizer. Said further agrochemically active compound may be in an effective amount or concentration or in amount or concentration such that the dilution of said composition for achieving an effective concentration of the compound of formula (I) also provides an effective concentration of said further agrochemically active compound. Suitable further agrochemically active are known in the art and will become apparent to the skilled person, in the view of the common general knowledge.

[0117] In other particular embodiments, the agrochemical composition of the third aspect of the invention further comprises an effective amount of one or more herbicides selected from paraquat (592), mesotrione (500), sulcotrione (710), clomazone (159), fentrazamide (340), mefenacet (491), oxaziclomefone (583), indanofan (450), glyphosate (407), prosulfocarb (656), molinate (542), triasulfuron (773), halosulfuron- methyl (414), and pretilachlor (632). The above herbicidal active ingredients are described, for example, in “The Pesticide Manual”, Editor C. D. S. Tomlin, 12th Edition, British Crop Protection Council, 2000, under the entry numbers added in parentheses; for example, mesotrione (500) is described therein under entry number 500.

[0118] In other particular embodiments, the agrochemical composition of the third aspect of the invention further comprises an effective amount of one or more fungicides selected from sedaxane, fludioxonil, penthiopyrad, prothioconazole, flutriafol, difenoconazole, azoxystrobin, captan, cyproconazole, cyprodinil, boscalid, diniconazole, epoxiconazole, fluoxastrobin, trifloxystrobin, metalaxyl, metalaxyl-M (mefenoxam), fluquinconazole, fenarimol, nuarimol, pyrifenox, pyraclostrobin, thiabendazole, tebuconazole, triadimenol, benalaxyl, benalaxyl-M, benomyl, carbendazim, carboxin, flutolanil, fuberizadole, guazatine, myclobutanil, tetraconazole, imazalil, metconazole, bitertanol, cymoxanil, ipconazole, iprodione, prochloraz, pencycuron, propamocarb, silthiofam, thiram, triazoxide, triticonazole, tolylfluanid, and a manganese compound (such as mancozeb, maneb).

[0119] In other particular embodiments, the agrochemical composition of the third aspect of the invention further comprises an effective amount of one or more of an insecticide, an acaricide, or a nematcide selected from thiamethoxam, imidacloprid, clothianidin, lamda-cyhalothrin, tefluthrin, beta-cyfluthrin, permethrin, abamectin, fipronil, and spinosad.

[0120] In other particular embodiments, the agrochemical composition of the third aspect of the invention comprises the compound of formula (I) in an effective concentration. The effective concentration of the compound of formula (I) varies in function of the activity of the compound of formula (I) employed in the composition of the third aspect of the invention and the plant or crop to which the composition is to be administered. The skilled person will be able to identify such effective concentration without undue burden.

[0121] In other particular embodiments, the agrochemical composition of the third aspect of the invention comprises the compound of formula (I) in a concentration of at least 100 nM; preferably of at least 1 ^M. In other particular embodiments, the agrochemical composition of the third aspect of the invention comprises the compound of formula (I) in a concentration of no more than 10 mM; preferably of no more than 1 mM; more preferably of no more than 500 ^M and even more preferably of no more than 100 ^M.

[0122] In other particular embodiments, the agrochemical composition of the third aspect of the invention comprises the compound of formula (I) in a concentration of about 50 ^M. This is particularly the case when the plant to be treated is maize or wheat. This is also particularly the case when the compound of formula (I) is the compound of formula (Ic).

[0123] In other particular embodiments, the agrochemical composition of the third aspect of the invention comprises the compound of formula (I) in a concentration of about 10 ^M. This is particularly the case when the plant to be treated is tomato. This is also particularly the case when the compound of formula (I) is the compound of formula (Ic).

[0124] As mentioned above, the fourth aspect of the invention relates to the use of the compound according to the first aspect of the invention or a salt, a solvate, a stereoisomer or a deuterated analogue thereof or of the agrochemical composition according to the third aspect of the invention in one or more of: (i) enhancing abiotic stress resistance in a plant, (ii) inhibiting seed germination in a plant, and / or (iii) reducing leaf transpiration in a plant.

[0125] As further detailed below, the compounds of formula (I) are active agonists of ABA receptors in plants and cause the closure of stomata in plants.

[0126] In further embodiments of the fourth aspect of the invention, the use of the compound according to the first aspect of the invention or a salt, a solvate, a stereoisomer or a deuterated analogue thereof or of the agrochemical composition according to the third aspect of the invention is for enhancing resistance of a plant to one or more of drought, soil salinity, water salinity, heat stress and cold stress. Preferably, the use of the compound according to the first aspect of the invention or a salt, a solvate, a stereoisomer or a deuterated analogue thereof or of the agrochemical composition according to the third aspect of the invention is for enhancing resistance of a plant to drought.

[0127] In further embodiments of the fourth aspect of the invention, the use of the compound according to the first aspect of the invention or a salt, a solvate, a stereoisomer or a deuterated analogue thereof or of the agrochemical composition according to the third aspect of the invention is for inhibiting seed germination in a plant.

[0128] In further embodiments of the fourth aspect of the invention, the use of the compound according to the first aspect of the invention or a salt, a solvate, a stereoisomer or a deuterated analogue thereof or of the agrochemical composition according to the third aspect of the invention is for reducing leaf transpiration in a plant.

[0129] In further embodiments of the fourth aspect of the invention, the use of the compound according to the first aspect of the invention or a salt, a solvate, a stereoisomer or a deuterated analogue thereof or of the agrochemical composition according to the third aspect of the invention is for closing stomata in a plant.

[0130] In further embodiments of the fourth aspect of the invention, the use of the compound according to the first aspect of the invention or a salt, a solvate, a stereoisomer or a deuterated analogue thereof or of the agrochemical composition according to the third aspect of the invention is as defined in any of the embodiments above and the plant is a plant selected from the group consisting of Arabidopsis thaliana, wheat, rice, maize, barley, sorghum, millet, oat, rye, quinoa, potato, sweet potato, cassava, yams, taro, sugarcane, sugar beet, soybeans, chickpeas, beans, lentils, peanuts, apples, bananas, oranges, mangoes, grapes, strawberries, blueberries, tomatoes, pineapples, avocados, papayas, watermelons, peaches, plums, cherries, carrots, broccoli, spinach, lettuce, cabbage, cauliflower, bell peppers, onions, garlic, peas, beans, eggplant, Brussels sprouts, radishes , pumpkins , chickpeas, , alfalfa, clover, palm, sunflower, canola, coconut, olive, cottonseed, coffee, cocoa, tea, tobacco, cotton, basil, thyme, rosemary, sage, oregano, mint, cilantro, turmeric, ginger, cinnamon and hops.

[0131] In further embodiments of the fourth aspect of the invention, the use of the compound according to the first aspect of the invention or a salt, a solvate, a stereoisomer or a deuterated analogue thereof or of the agrochemical composition according to the third aspect of the invention is as defined in any of the embodiments above and the plant is a crop plant selected from the group consisting of wheat, rice, maize, barley, sorghum, millet, oat, rye, quinoa, potato, sweet potato, cassava, yams, taro, sugarcane, sugar beet, soybeans, chickpeas, beans, lentils, peanuts, apples, bananas, oranges, mangoes, grapes, strawberries, blueberries, tomatoes, pineapples, avocados, papayas, watermelons, peaches, plums, cherries, carrots, broccoli, spinach, lettuce, cabbage, cauliflower, bell peppers, onions, garlic, peas, beans, eggplant, Brussels sprouts, radishes , pumpkins , chickpeas, , alfalfa, clover, palm, sunflower, canola, coconut, olive, cottonseed, coffee, cocoa, tea, tobacco, cotton, basil, thyme, rosemary, sage, oregano, mint, cilantro, turmeric, ginger, cinnamon and hops.

[0132] In further embodiments of the fourth aspect of the invention, the use of the compound according to the first aspect of the invention or a salt, a solvate, a stereoisomer or a deuterated analogue thereof or of the agrochemical composition according to the third aspect of the invention is as defined in any of the embodiments above and the plant is a plant selected from the group consisting of Arabidopsis thaliana, wheat, rice, maize, barley, sorghum, millet, oat, rye, quinoa, potato, sugarcane, sugar beet, soybeans, chickpeas, beans, lentils, tomatoes, watermelons, peas, beans, eggplant, pumpkins, alfalfa, palm, sunflower, coconut, olive and cottonseed.

[0133] In further embodiments of the fourth aspect of the invention, the use of the compound according to the first aspect of the invention or a salt, a solvate, a stereoisomer or a deuterated analogue thereof or of the agrochemical composition according to the third aspect of the invention is as defined in any of the embodiments above and the plant is a plant selected from the group consisting of Arabidopsis thaliana, wheat, tomato and maize.

[0134] In further embodiments of the fourth aspect of the invention, the use of the compound according to the first aspect of the invention or a salt, a solvate, a stereoisomer or a deuterated analogue thereof or of the agrochemical composition according to the third aspect of the invention is made by any method known to the skilled person for administering agrochemically active compounds or compositions to plant or crop. Those include, among others, spraying, atomizing, dipping, pouring, irrigating, dusting or scattering the compositions over the plant or the soil hosting the plant, in particular liquid compositions, or brushing or pouring or otherwise contacting the composition over the plant or the soil hosting the plant. The composition of the third aspect of the invention may be formulated in a manner that it is suitable for the chosen administration mode.

[0135] As mentioned above, the fifth aspect of the invention relates to a plant seed comprising or coated with the compound according to the first aspect of the invention or a salt, a solvate, a stereoisomer or a deuterated analogue thereof or the agrochemical composition according to the third aspect of the invention.

[0136] In preferred embodiments of the fifth aspect of the invention, the plant seed comprises or is coated with the compound of formula (I) as defined in any of the embodiments defined above for the first aspect of the invention or with an agrochemical composition as defined in any of the embodiments defined above for the third aspect of the invention.

[0137] In preferred embodiments of the fifth aspect of the invention, the plant seed is a seed of a plant as defined in any of the embodiments defined above for the fourth aspect of the invention.

[0138] Methods for the preparation of said seed are known in the art and will become apparent to the skilled person upon reduction to practice of the invention. Those include film coating, encrusting, pelleting, powder coating, seed encapsulation, primed seed coating, inoculation and preinoculation.

[0139] Throughout the description and claims the word “comprises" and variations of the word, are not intended to exclude other technical features, additives, components or steps. Furthermore, the word “comprise” encompasses the cases of “consist of” and “consists essentially of”. Additional objects, advantages and features of the invention will become apparent to those skilled in the art upon examination of the description or may be learned by practice of the invention. The following examples are provided by way of illustration, and they are not intended to be limiting of the present invention. EXAMPLES

[0140] The process of certain embodiments of the second aspect of the invention may further be described by the following synthetic scheme: 1: preparation of 4-((1,3-dioxoisoindolin-2-

[0141] To a solution of 4-(bromomethyl)benzonitrile (10 g, 51.00 mmol, 1.0 eq.), in acetonitrile (100 mL), potassium phthalimide (9.45 g, 51.00 mmol, 1.0 eq.) was added. The reaction mixture was refluxed under nitrogen atmosphere for 26 h. Volatiles were removed under reduced pressure and the residue was purified by column chromatography (20-100% EtOAc / Hexane and 15% MeOH / DCM to afford 4-((1,3- dioxoisoindolin-2-yl)methyl)benzonitrile 1 (12.1 g, 90%) as a white solid. GC-MS: m / z 262 (M+) of 2-bromo-4-((1,3-dioxoisoindolin-2- yl)methyl)benzonitrile (Va)

[0142] Method A: To a solution of 4-((1,3-dioxoisoindolin-2-yl)methyl)benzonitrile 1 (6.00 g, 22.88 mmol, 1 eq.) in DCE (60 mL), N-bromosuccinimide (4.48 g, 25.17 mmol, 1.1 eq.), Pd(OAc)2 (0.26 g, 1.14 mmol, 0.05 eq.) and (±)-camphor sulfonic acid (2.65 g, 11.44 mmol, 0.5 eq.) were added. The reaction mixture was heated under nitrogen atmosphere at 70 ºC for 23 h. Volatiles were removed under reduced pressure and the residue was purified by column chromatography (1% MeOH / DCM) to obtain 2-bromo-4- ((1,3-dioxoisoindolin-2-yl)methyl)benzonitrile 2 (2.00 g, 26%) as a white solid, containing 13% of the dibrominated byproduct. GC-MS: m / z 342 / 340 (1:1, MH+)

[0143] Method B: To a solution of 2-Bromo-4-(bromomethyl)benzonitrile (725 mg, 2.505 mmol, 1 eq) in DMF (20 mL), phthalimide potassium salt (696 mg, 3.757 mmol, 1.5 eq) was added. The reaction mixture was stirred at 100 °C for 4 h and then at r.t. for 14 h. The mixture was poured into H2O (40 mL) and extracted with CH2Cl2 (2 x 30 mL). The organic layer was washed with brine (2 x 30 mL), dried over ahydrous Na2SO4, filtered and concentrated. The solid was slurred with Et2O (2 x 5 mL) to afford a beige solid (930 mg). It was purified by column chromatography (0-1% MeOH / CH2Cl2) to afford 2-bromo- 4-((1,3-dioxoisoindolin-2-yl)methyl)benzonitrile 2 (741 mg, 87%) as a white solid. GC-MS: m / z 340 (M+) Preparative example 3: preparation of 2,6-dibromo-4-((1,3-dioxoisoindolin-2- yl)methyl)benzonitrile (Vb)

[0144] To a solution of 4-((1,3-dioxoisoindolin-2-yl)methyl)benzonitrile (6.00 g, 22.88 mmol, 1 eq.) in DCE (60 mL), N-bromosuccinimide (10.18 g, 57.20 mmol, 2.5 eq.), Pd(OAc)2 (0.26 g, 1.14 mmol. 0.05 eq.) and (±)-camphor sulfonic acid (2.65 g, 11.44 mmol, 0.5 eq.) were added. The reaction mixture was heated under nitrogen atmosphere at 70 ºC for 72 h. More Pd(OAc)2 (0.26 g, 1.14 mmol.0.05 eq.) and N-bromosuccinimide (4.06 g, 22.88 mmol, 1 eq.) were added and the mixture was allowed to stir at 70 ºC for 24 h. Volatiles were removed under reduced pressure and to the residue was added DCM (100 mL), water (50 mL) and 10% aq. NaOH (50 mL). The organic layer was decanted and the aqueous layer was extracted with DCM (3 x 80 mL). The combined organic layer was dried over anh. Na2SO4, filtered and concentrated. The residue was purified by column chromatography (0-1% MeOH / DCM). Fractions containing product was combined. DCM (100 mL) was added and the mixture was allowed to stir overnight. The solid was filtered to afford 2,6-dibromo-4-((1,3-dioxoisoindolin-2- yl)methyl)benzonitrile (2.53 g, 32%) as a white solid, containing 10% of the monobrominated byproduct. GC-MS: m / z 420 (M+) Preparative example 4: preparation of (V’a) or (V’b) by Suzuki coupling with compounds of formula R4-B(OH)2

[0145] General procedure A: To a solution of intermediate 2-bromo-4-((1,3- dioxoisoindolin-2-yl)methyl)benzonitrile (390 mg, 1.143 mmol, 1 eq.) in Toluene / Water (8:2, 10 mL), the corresponding boronic acid (2.858 mmol, 2.5 eq.), and potassium phosphate tribasic (4970.6 mg, 4.572 mmol, 4 eq.) were added. After degassing the reaction mixture, Pd(OAc)2 (12.8 mg, 0.057 mmol, 0.05 eq.) and PCy3 (32.1 mg, 0.114 mmol, 0.1 eq.) were added. The reaction mixture was heated under inert atmosphere at 100 ºC for 18 h. The reaction mixture was allowed to reach r.t., poured into sat. aq. sol. NaHCO3 (40 mL) and extracted with EtOAc (3 x 20 mL). The organic layer was washed with H2O (30 mL), brine (30 mL), dried over anhydrous Na2SO4, filtered and concentrated. Purification of the crude product by column chromatography (EtOAc / Hexmixture) afforded the corresponding products (V’a) or (V’b) as white / pale solids. Purityand structure were confirmed by GC-MS and1H-NMR techniques.

[0146] When R4 is a saturated alkyl or cycloalkyl group, the compounds of formula (V’a) and (V’b) are compounds of formula (IV).

[0147] In particular, this procedure was employed to prepare the following compounds using a boronic acid compound wherein R4 is cyclopropyl : 2-cyclopropyl-4-((1,3-dioxoisoindolin-2-yl)methyl)benzonitrile having a GC-MS of 302 m / z (M+); and 2,6-dicyclopropyl-4-((1,3-dioxoisoindolin-2-yl)methyl)benzonitrile. Preparative example 5: preparation of (V’a) or (V’b) by Suzuki coupling with compounds of formula R4-BF3K

[0148] General procedure B: To a solution of intermediate 2-bromo-4-((1,3-dioxoisoindolin-2-yl)methyl)benzonitrile (0.30 g, 0.88 mmol,1 eq.) in Toluene / Water (9:1, 0.15M), the corresponding potassium trifluoroborate compound (1.32 mmol, 1.5 eq.), and potassium phosphate tribasic (0.56 g, 2.64 mmol, 3 eq.) were added. After degassing the reaction mixture, Pd(OAc)2 (0.01 g, 0.04 mmol, 0.05 eq.) and Ruphos (0.04 g, 0.09 mmol , 0.1 eq.) were added. The reaction mixture was heated under nitrogen atmosphere at 70 ºC for 44 h. Volatiles were removed under reduced pressure and the residue was filtered through Celite© pad and eluted with EtOAc (3 x 15 mL). The filtrate was washed with sat. aq. NaHCO3 (20 mL), water (20 mL) and brine (20 mL). The organic phase was dried over anh. Na2SO4, filtered and concentrated. The crude product was purified by flash column chromatography (EtOAc / Hexane mixture) to afford the corresponding products (V’a) or (V’b) as white / pale solids. Purity and structure were confirmed by GC-MS and1H-NMR techniques.

[0149] When R4 is a saturated alkyl or cycloalkyl group, the compounds of formula (V’a) and (V’b) are compounds of formula (IV).

[0150] In particular, this procedure was employed to prepare the following compounds using a trifluoroborate compound wherein R4 is selected from the group consisting of vinyl, propen-1-yl and prop-1-en-2-yl: 4-((1,3-dioxoisoindolin-2-yl)methyl)-2-vinylbenzonitrile having a GC-MS of 288 m / z (M+); 4-((1,3-dioxoisoindolin-2-yl)methyl)-2-(prop-1-en-2-yl)benzonitrile having a GC-MS of 302 m / z (M+); 4-((1,3-dioxoisoindolin-2-yl)methyl)-2-(prop-1-en-1-yl)benzonitrile having the following1H NMR peaks (300 MHz, CDCl3): δ 7.93 – 7.81 (m, 2H), 7.74 (dd, J = 5.4, 3.0 Hz, 2H),7.63 (s, 1H), 7.54 (d, J = 8.0 Hz, 1H), 7.31 (d, J = 7.9 Hz, 1H), 6.76 – 6.65 (m, 1H), 6.47 (dq, J = 14.0, 6.7 Hz, 1H), 4.83 (d, J = 9.0 Hz, 2H), 1.94 (dt, J = 7.3, 2.1 Hz, 3H); 4-((1,3-dioxoisoindolin-2-yl)methyl)-2,6-divinylbenzonitrile having a GC-MS of 314 m / z (M+); 4-((1,3-dioxoisoindolin-2-yl)methyl)-2,6-di(prop-1-en-2-yl)benzonitrile having a GC-MS of 342 m / z (M+); and 4-((1,3-dioxoisoindolin-2-yl)methyl)-2,6-di(prop-1-en-1-yl)benzonitrile having a GC-MS of 342 m / z (M+). Preparative example 6: Preparation of a compound of formula (IV) by hydrogenation of compounds (V’a) or (V’b) when R4 is an alkenyl or cycloalkenyl group

[0151] General Procedure C: 10% Pd / C (0.02 g, 55% wet) was charged into a flask and evacuate and back-fill with nitrogen 3 times. A solution of unsaturated intermediate (V’a) or (V’b) (0.80 mmol, 1 eq.) in EtOH (20 mL), was added. The nitrogen atmosphere was evacuated and back-filled with hydrogen gas. The reaction was stirred at room temperature for 16 h. Upon completion, the reaction mixture was filtered through Celite© pad eluting with MeOH and EtOAc. Volatiles were removed under reduced pressure to afford product compound of formula (IV) (100%) as a white solid. The product compound of formula (IV) (usually as a pale solid) was used in the next step without further purification. Purity and mass were confirmed by GC-MS technique.

[0152] In particular, this procedure was employed to prepare the following compounds: 4-((1,3-dioxoisoindolin-2-yl)methyl)-2-ethylbenzonitrile having a GC-MS of 290 m / z (M+); 4-((1,3-dioxoisoindolin-2-yl)methyl)-2-isopropylbenzonitrile having a GC-MS of 304 m / z (M+); 4-((1,3-dioxoisoindolin-2-yl)methyl)-2-propylbenzonitrile having a GC-MS of 304 m / z (M+); 4-((1,3-dioxoisoindolin-2-yl)methyl)-2,6-diethylbenzonitrile having a GC-MS of 318 m / z (M+); 4-((1,3-dioxoisoindolin-2-yl)methyl)-2,6-diisopropylbenzonitrile; and 4-((1,3-dioxoisoindolin-2-yl)methyl)-2,6-dipropylbenzonitrile having a GC-MS of 346 m / z (M+). Preparative example 7: Preparation of a compound of formula (II) from a compound of formula (IV)

[0153] General Procedure D: To a solution of the compound of formula (IV) (0.86 mmol, 1 eq.) in EtOH (15 mL), hydrazine monohydrate (0.24 mL, 5.16 mmol, 6 eq.) was added. The reaction was heated at 90 ºC for 2 h. Upon completion, the reaction mixture was filtered, and volatiles were removed under reduced pressure to afford the desired product of formula (II) as a yellow solid. It was used in the next step without further purification. Purity and mass were determined using GC-MS and HPLC-MS techniques.

[0154] In particular, this procedure was employed to prepare the following compounds: 4-(aminomethyl)-2-cyclopropylbenzonitrile having a GC-MS of 172 m / z (M+); 4-(aminomethyl)-2-ethylbenzonitrile having a GC-MS of 159 (M-H); 4-(aminomethyl)-2-isopropylbenzonitrile having a GC-MS of 174 m / z (M+); 4-(aminomethyl)-2-propylbenzonitrile; 4-(aminomethyl)-2,6-dicyclopropylbenzonitrile having a GC-MS of 212 m / z (M+); 4-(aminomethyl)-2,6-diethylbenzonitrile having a GC-MS of 187 (M-H); 4-(aminomethyl)-2,6-diisopropylbenzonitrile having a GC-MS of 215 (M-H); and 4-(aminomethyl)-2,6-dipropylbenzonitrile having a GC-MS of 215 (M-H). Preparation of a compound of formula (I) from a compound of formula (II) and (III)

[0155] General Procedure E: To a solution of the starting compound of formula (II) (0.593mmol, 1 eq.) in DMF (1.5 mL) sulfonyl chloride of formula (III) (4-methylpiperidine-1- sulfonyl chloride or 4-trifluoromethylpiperidine-1-sulfonyl chloride, purchased from Enamine, N-morpholinylsulfonyl chloride, purchased from BLDpharm, or p- toluenesulfonyl chloride, purchased from Fluorochem, 0.593 mmol, 1 eq.,) and DIPEA (0.31 mL, 1.77 mmol, 3 eq.) were added. The reaction mixture was stirred at room temperature. for 3 h.1M Na2CO3 solution (25 mL) was added and extracted with EtOAc (2x15 mL). The combined organic layer was washed with 1M Na2CO3 solution (20 mL), water (20 mL) and brine (20 mL), filtered, concentrated at vacuum, and the residue was purified by column chromatography (EtOAc / Hexanes mixture) and semipreparative HPLC when needed to afford the desired compound of formula (I). Products presented a purity above 95%. Purity and mass were determined by UPLC-MS Structure was determined by1H-RMN (CDCl3).

[0156] General Procedures A or B, C when R4 is an alkenyl or a cycloalkenyl group, D and E described above were used in the preparation of the compounds of formulae (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ih), (Ij), (Ik), (Il), (Im), (In), (Ip), (Iq), (Ir), (Is) and (It) described herein. Table 1 summarizes the procedures, reagents and yields for the preparation of these compounds: Table 1 Proc Procedure Overall yield Compound R4edure A or B C carried Z Y R3 from out? (Va) / (Vb) (%) (Ia) vinyl B Yes A CHR3 Me 26 (Ib) Propen-1-yl B Yes A CHR3 Me 73(Ic) cyclopropyl A - A CHR3Me 17 (Id) cyclopropyl A - A CHR3 Me 22 (Ie) Isopropenyl B Yes A CHR3 Me 22(If) vinyl B Yes A CHR3 Me 21 (Ih) vinyl B Yes A CHR3 CF3 17 (Ij) Propen-1-yl B Yes A CHR3 CF3 4(Ik) Cyclopropyl A - A CHR3 CF3 97(Il) Isopropenyl B Yes A CHR3 CF3 14(Im) vinyl B Yes A CHR3 CF3 24 (In) Propen-1-yl B Yes A CHR3 CF3 11(Ip) isopropenyl B Yes A CHR3 CF3 14(Iq) Cyclopropyl A - A CHR3 H 6(Ir) Cyclopropyl A - A O - 18(Is) Cyclopropyl A - A NR3 Me 14(It) Cyclopropyl A - B - Me 5

[0157] Table 2 below reports the1H NMR data for the prepared compounds, as measured in CDCl3 unless otherwise indicated and at 300 MHz. Table 2 Compound1H NMR peaks (CDCl3, 300 MHz) HPLC-MS m / z (M-H) δ* 7.75 (dd, J = 8.7, 3.7 Hz, 2H), 7.44 (s, 1H), 7.35 (dt, J= 8.1, 2.3 Hz, 1H), 4.14 (d, J = 3.0 Hz, 2H), 3.43 (dd, J = 11.9, 3.6 Hz, 2H), 2.79 (qd, J = 7.6, 2.8 Hz, 2H), 2.68 – (Ia) 2.49 (m, 2H), 1.69 – 1.52 (m, 2H), 1.47 – 1.31 (m, 1H), 320 1.33 – 1.17 (m, 3H), 0.97 (dd, J = 14.3, 10.3 Hz, 2H), 0.86 (dd, J = 6.8, 2.8 Hz, 3H)δ 7.56 (d, J = 7.9 Hz, 1H), 7.33 – 7.19 (m, 2H), 4.56 –4.44 (m, 1H), 4.21 (d, J = 6.3 Hz, 2H), 3.62 (d, J = 10.9 (Ib) Hz, 2H), 2.80 (d, J = 7.4 Hz, 2H), 2.76 – 2.54 (m, 2H), 334 1.88 – 1.58 (m, 4H), 1.49 –1.42 (m, 1H), 1.16 (td, J = 14.3, 10.0 Hz, 2H), 1.02 – 0.76 (m, 6H) δ7.57 (d, J = 7.9 Hz, 1H), 7.24 – 7.14 (m, 1H), 6.91 (s,1H), 4.42 (d, J = 6.4 Hz, 1H), 4.20 (d, J = 6.3 Hz, 2H), 3.64 (d, J = 11.9 Hz, 2H), 2.68 (td, J = 12.2, 2.6 Hz, 2H), (Ic) 2.28 (ddd, J = 13.5, 8.6, 5.1 Hz, 1H), 1.67 (d, J = 13.3 Hz, 332 2H), 1.45 (d, J = 11.6 Hz, 1H), 1.29 – 1.04 (m, 4H), 0.94 (d, J = 6.5 Hz, 3H), 0.80 (dt, J = 6.7, 4.8 Hz, 2H) δ6.72 (s, 2H), 4.38 (t, J = 6.3 Hz, 1H), 4.16 (d, J = 6.3Hz, 2H), 3.65 (dt, J = 12.4, 3.7 Hz, 2H), 2.70 (td, J = 12.2, (Id) 2.6 Hz, 2H), 2.32 (tt, J = 8.3, 5.1 Hz, 2H), 1.78 – 1.62 (m, 372 2H), 1.55 – 1.37 (m, 1H), 1.31 – 1.05 (m, 6H), 0.96 (d, J = 6.5 Hz, 3H), 0.79 (dt, J = 6.6, 4.8 Hz, 4H) δ7.17 (s, 2H), 4.50 – 4.38 (m, 1H), 4.35 – 4.13 (m, 2H),3.66 (d, J = 11.9 Hz, 2H), 3.41 (p, J = 6.9 Hz, 2H), 2.76 – (Ie) 2.58 (m, 2H), 1.73 – 1.60 (m, 2H), 1.55 – 1.37 (m, 1H), 376 1.30 (d, J = 6.8 Hz, 12H), 1.22 – 1.01 (m, 2H), 0.93 (d, J = 6.5 Hz, 3H) δ7.13 (s, 2H), 4.50 – 4.38 (m, 1H), 4.22 (d, J = 6.3 Hz,2H), 3.66 (d, J = 12.1 Hz, 2H), 2.86 (q, J = 7.6 Hz, 4H), (If) 2.69 (td, J = 12.2, 2.6 Hz, 2H), 1.67 (d, J = 13.2 Hz, 2H), 348 1.51 – 1.35 (m, 1H), 1.29 (t, J = 7.6 Hz, 6H), 1.15 (tt, J = 15.1, 7.7 Hz, 2H), 0.93 (d, J = 6.5 Hz, 3H) δ7.56 (d, J = 7.9 Hz, 1H), 7.34 – 7.10 (m, 2H), 4.50 –4.38 (m, 1H), 4.21 (d, J = 5.9 Hz, 2H), 3.76 (d, J = 12.7 (Ih) Hz, 2H), 2.84 (q, J = 7.6 Hz, 2H), 2.75 – 2.57 (m, 2H), 374 1.88 (d, J = 13.3 Hz, 2H), 1.51 – 1.35 (m, 3H), 1.31 – 1.15 (m, 3H) δ7.58 (d, J = 8.0 Hz, 1H), 7.20 (d, J = 8.0 Hz, 1H), 6.90(s, 1H), 4.50 – 4.38 (m, 1H), 4.21 (d, J = 6.1 Hz, 2H), 3.78 (Ij) (d, J = 12.5 Hz, 2H), 3.48 (q, J = 7.0 Hz, 2H), 2.70 (t, J = 386 12.2 Hz, 2H), 2.35 – 2.23 (m, 1H), 2.20 – 2.01 (m, 1H), 1.92 (d, J = 13.8 Hz, 2H), 1.20 (q, J = 6.3 Hz, 4H) δ6.67 (d, J = 1.9 Hz, 2H), 4.50 – 4.38 (m, 1H), 4.13 (d, J= 6.2 Hz, 2H), 3.76 (d, J = 12.5 Hz, 2H), 2.69 (t, J = 12.4 (Ik) Hz, 2H), 2.29 (td, J = 8.5, 4.3 Hz, 2H), 2.20 – 1.99 (m, 426 1H), 1.92 (d, J = 13.4 Hz, 2H), 1.55 – 1.40 (m, 2H), 1.22 – 1.06 (m, 4H), 0.84 – 0.68 (m, 4H) δ7.16 (s, 2H), 4.50 – 4.38 (m, 1H), 4.24 (d, J = 6.2 Hz,2H), 3.81 (d, J = 12.4 Hz, 2H), 3.50 – 3.33 (m, 2H), 2.71 (Il) (t, J = 12.1 Hz, 2H), 2.20 – 1.99 (m, 1H), 1.92 (d, J = 13.0 430 Hz, 2H), 1.55 – 1.40 (m, 2H), 1.30 (d, J = 6.9 Hz, 12H) δ7.14 (s, 2H), 4.50 – 4.38 (m, 1H), 4.24 (d, J = 6.1 Hz,2H), 3.82 (d, J = 12.0 Hz, 2H), 2.89 (q, J = 7.6 Hz, 4H), (Im) 2.74 (td, J = 12.5, 2.6 Hz, 2H), 2.23 – 2.05 (m, 1H), 2.01 402 – 1.87 (m, 2H), 1.66 – 1.45 (m, 2H), 1.31 (t, J = 7.6 Hz, 6H) δ7.09 (s, 2H), 4.50 – 4.38 (m, 1H), 4.21 (d, J = 6.2 Hz,(In) 2H), 3.80 (d, J = 12.6 Hz, 2H), 2.81 (t, J = 7.8 Hz, 4H), 430 2.71 (t, J = 12.3 Hz, 2H), 2.23 – 2.05 (m, 1H), 1.93 (d, J = 13.6 Hz, 2H), 1.69 (q, J = 7.5 Hz, 4H), 1.66 – 1.45 (m, 2H), 0.99 (t, J = 7.3 Hz, 6H) δ7.60 (d, J = 7.9 Hz, 1H), 7.34 (s, 1H), 7.30 – 7.23 (m,1H), 4.50 – 4.38 (m, 1H), 4.26 (d, J = 6.2 Hz, 2H), 3.80 (Ip) (d, J = 12.6 Hz, 2H), 3.39 (p, J = 7.0 Hz, 1H), 2.70 (t, J = 388 12.4 Hz, 2H), 2.23 – 2.05 (m, 1H), 1.92 (d, J = 13.5 Hz, 2H), 1.66 – 1.45 (m, 2H), 1.31 (d, J = 7.0 Hz, 6H) δ7.57 (d, J = 7.9 Hz, 1H), 7.21 (d, J = 7.9 Hz, 1H), 6.91(s, 1H), 4.43 (m, 1H), 4.21 (d, J = 6.2 Hz, 2H), 3.15 (t, J = (Iq) 5.1 Hz, 4H), 2.27 (td, J = 8.5, 4.3 Hz, 1H), 1.65 – 1.42 (m, 318 6H ), 1.28 – 1.10 (m, 2H), 0.80 (dt, J = 6.5, 4.8 Hz, 2H) δ7.58 (d, J = 7.8 Hz, 1H), 7.21 (d, J = 7.9 Hz, 1H), 6.91(s, 1H), 4.55 (m, 1H), 4.24 (d, J = 6.2 Hz, 2H), 3.68 (dd, J (Ir) = 5.7, 3.9 Hz, 4H), 3.16 (dd, J = 5.6, 3.7 Hz, 4H), 2.28 (td, 320 J = 8.5, 4.2 Hz, 1H), 1.28 – 1.09 (m, 2H), 0.86 – 0.74 (m, 2H). δ7.57 (d, J = 7.9 Hz, 1H), 7.21 (d, J = 8.0 Hz, 1H), 6.90(s, 1H), 4.58 (m, 1H), 4.22 (d, J = 6.2 Hz, 2H), 3.22 (t, J = (Is) 4.9 Hz, 4H), 2.41 (t, J = 5.0 Hz, 4H), 2.30 (s, 3H), 2.35 – 333 2.20 (m, 1H), 1.23 – 1.10 (m, 2H), 0.86 – 0.74 (m, 2H). δ7.75 – 7.67 (m, 2H), 7.48 (d, J = 8.0 Hz, 1H), 7.34 –7.23 (m, 2H), 7.11 – 7.03 (m, 1H), 6.74 (s, 1H), 4.85 (m, (It) 1H), 4.13 (d, J = 6.4 Hz, 2H), 2.44 (s, 3H), 2.20 (td, J = 325 8.2, 4.2 Hz, 1H), 1.17 – 1.04 (m, 2H), 0.75 – 0.63 (m, 2H). * measured in DMSO –d6instead of CDCl3Example 2: Evaluation of agonist activity of ABA receptors of the compounds of formula (I) General procedure for seed germination experiments

[0158] The compound of formula (I) to be tested or control compounds were included in MS media (Murashige-Skoog medium, the composition of which is known in the art) at the indicated concentration. Sterile Arabidopsis or tomato seed were sown in the media and stratified for 3 days at 4 ^C. Pictures were taken 3 days (Arabidopsis) and 7 days (tomato) after transferring the plates to the growth chamber. To determine the IC50 values of ABA, OP and (Ic) on seed germination, Col-0 Arabidopsis seed were sterilized and sown on MS media supplemented with 8 different concentrations of compound (0, 10, 25, 50, 100, 250, 500, 1000 nM). Seeds were stratified for 3 days at 4 ^C and % germination was scored 24 hours after transferring the plates to the growth chamber. The experiment was performed in triplicate using 50-75 seeds per replicate. The germination mean ^ SD was adjusted to a dose-response curve with GraphPad Prism 9 to calculate IC50 values. The experiment was repeated twice. Figure 1(d) shows the results of the IC50 value determination for (Ic), opabactin and ABA. Figure 2(c) shows the results of seed germination experiments carried out with ABA, (It), (Ic) and cyanabactin. The results of Figure 2(c) show that the compounds of formula (It) and (Ic) are more active than ABA and cyanabactin.

[0159] The results of figure 1 show that the compounds of formula (I) efficiently delay seed germination for Arabidopsis. General procedure for luciferase experiments

[0160] 7 days-old seedlings of the ABA-inducible reporter line pMAPKKK18-LUC+ grown on MS liquid media were treated with solutions of the different ligands at 0.5 ^M or 2.5 ^M in MS liquid media and luminescence was quantified 6 hours after the treatment, as disclosed in García-Maquilón I, Rodriguez PL, Vaidya AS, Lozano-Juste J. A Luciferase Reporter Assay to Identify Chemical Activators of ABA Signaling. Methods Mol Biol.2021; 2213:113-121, the content of which is herein incorporated by reference. The results of these experiments are shown in Figure 2(a) and Figure 2(b). According to these results, the compound of formula (I) are suitable ligands for ABA receptors and are suitable chemical activators of ABA signaling pathways. ABA, cyanabactin (CB) and opabactin (OP) were used as control experiments. All the compounds of formula (I) that were tested are at least as active as ABA. Compounds (Ia), (Ib), (Ic) and (Ij) proved particularly active. In addition, the compounds of formula (Ic) and (It) were surprisingly and unexpectedly found as being particularly active. These compounds are in particular more active than cyanabactin. Compounds of formula (I) are thus suitable for increasing the resistance of the plant to abiotic stress. General procedure for in vitro IC50 determination

[0161] In vitro IC50 values of the different compounds of formula (I) was determined as follows. Recombinant receptor and PP2C proteins were used in enzymatic phosphatase assays using 4-Methylumbelliferyl phosphate (4-MUP) as substrate. The proteins were purified and stored in an aqueous solution of 50 mM Tris pH = 8.0, 150 mM KCl, 0.1 % v / v tween20, 20% v / v glycerol, 10 mM 2-mercaptoethanol (2-ME).80 ^L of a solution of 0.125% v / v 2-ME, 12.5 mM MnCl2, 3 ^g BSA containing PP2C dNHAB1 at 50 nM, and receptors from different plant species at a concentration of 100 nM for Arabidopsis receptors and 200 nM for maize receptors were prepared. 1 ^L of the compound of formula (I) at the tested concentration in DMSO was then added (final concentrations of 0.1, 1, 30, 50, 100, 200, 1000, 10000 nM). After an incubation of 20 minutes, 20 ^L of substrate aqueous solution (5 mM 4-MUP, 16.5 mM Tris-HAc, 33 mM KOAc) was added and the fluorescence (355 nm / 460 nm) measured for 20 minutes. 100% PP2C activity was given to the reactions without ligands and % inhibition was calculated accordingly. Different ligand concentrations (final concentrations 0.1, 1, 30, 50, 100, 200, 1000, 10000 nM) were used to fit the % inhibition into a dose-response curve to calculate IC50 values with GraphPad Prism 9.

[0162] Table 3 below summarizes the IC50 values, expressed in nM, obtained for ABA and the compound of formula (Ic). As will be obvious to the skilled person, all experiments described herein and using ABA as ligand are provided for comparison purposes. Table 3 Plant Arabidopsis Maize Receptor AtPYL1 AtPYL5 AtPYL8 ZmPYL1 ZmPYL2 ZmPYL3 ZmPYL13ABA 118.4 7.93 40.57 86.36 128.2 48.48 13.98 (Ic) 7.46 9.54 191.8 4.37 2.97 20.9 6.74

[0163] The results of Table 3 show that the compound of formula (I) exhibit high affinity for ABA receptors and show improved activity over ABA in some cases. These compounds are thus useful agonists for said receptors and are suitable for increasing the plant's ability to withstand abiotic stress, such as stress related to drought, salinity and cold. General procedure for thermal imaging

[0164] For thermal imaging experiments using tomato, plants were treated by spray with a solution of 10 mM MES pH = 5.7, 0.02 % silweet including the compounds to be tested at the indicated concentrations. Infra-red images were acquired 24 hours after the treatment with a Flir E95 thermal camera. Temperature was quantified using the Flir tools software. At least 6 plants per treatment were used in each experiment and 15 measurements were taken for each plant. The experiment was repeated 3 times. The mean temperature difference compared to control treated plants ^ SD are reported in Figure 7.

[0165] For thermal imaging experiments using wheat plants, we treated 2 week-old plants with 50 ^M of ABA, (Ic) in 10 mM MES pH 5.7, 0.05% tween20 or 0.1% DMSO v / v in 10 mM MES pH 5.7, 0.05% tween20 as control and thermal images were acquired 16 hours after the treatment. Images were quantified and average leaf temperature calculated. Mean values ^ SD are reported in Fig. 9b.

[0166] The results of Figure 7 and Figures 9a and 9b show that (lc) is able to produce stomata closure and reduce plant transpiration through stomata in some cases with more activity than ABA Infra Red Gas analysis in tomato plants (IRGA)

[0167] For IRGA analysis using tomato plants, 1 month old plants grown under 16 / 8 h light / dark photoperiod (24 / 20 ºC) in growth chamber were used. Plants were treated by spray with 10 mM MES pH = 5.7, 0.02 % silweet containing the indicated ligands at a concentration of 10 ^M. IRGA measurements were taken 1 hour after light onset each day for 5 consecutive days in the same fully expanded leaves (4th leaf from the apex). Net rate of CO2 fixation (AN), stomatal conductance (gs), transpiration rate (E), sub- stomatal CO2 concentration (Ci) and PSII efficiency (PhiPS2) parameters were determined with a LI-6400 (LICOR Environmental, Nebraska, USA). Measurements were performed at steady state conditions under saturating light (1000 mmol / m2·s) and 420 ppm CO2. Twelve plants per treatment were used.

[0168] The results of Figure 6 show that spraying the compound of Formula (Ic) on tomato plants is suitable for reducing significantly the stomatal conductance of tomato plants. This decrease of stomatal conductance allows the plant to minimize water loss through transpiration which produces the following effects: (i) the plant retains water; (ii) plant wilting is prevented; (iii) entry of some pathogens is reduced. Infra Red Gas analysis in maize plants (IRGA)

[0169] For IRGA analysis using maize, plants were grown on growth chamber incontrolled conditions at 25 °C, 16 h light (300–400 μmol m−1 s−1) and 60–70% relativehumidity. Plants at v3 stage (third leaf totally expanded) were treated with 5 mL of 50 ^M of ABA, (Ic) or 0.1% DMSO (v / v) as control in a solution containing 10 mM MES pH = 5.7, 0.05% Tween 20 and subjected to 2 different watering conditions, 100% (well- watered, WW) and 50% (water-deficit, WD) of field capacity (as shown in Figure 10a). Gas exchange analyses were carried out on the fully developed leaves (N = 30). Photosynthesis (Pn), stomatal conductance (Gs), and transpiration rate (E) were measured on the attached leaves using a portable infrared gas analyzer (LCPro, BioScientific Ltd., Hoddesdon, UK). Measurements were made at environmentCO2 concentration, a photosynthetic photon flux density (PPFD) of 800 μmol m–2 s–1(optimized with a light curve), and a cuvette airflow of 500 mL min–1. Soil humidity was measured into de pots using a TEROS 12 sensor (PESSL INSTRUMENTS GmbH, Weiz, Austria).

[0170] The results of Figure 10b show that the compound of Formula (Ic) is suitable for reducing significantly the stomatal conductance of well-watered maize plants. This decrease of stomatal conductance allows the plant to minimize water loss through transpiration which produces the following effects: (i) the plant retains water; (ii) plant wilting is prevented; (iii) entry of some pathogens is reduced.

[0171] The results of Figures 10c show that the intake of carbon dioxide for photosynthesis of maize plants placed in drought conditions drops suddenly 4 days after the drought treatment. This drop in photosynthesis is delayed when the plant is treated with the compound of formula (Ic). Surprisingly, said delay is higher than when the plant is treated with ABA. As known in the art, the closing of stomata leads to a reduction of stomatal conductance and a reduction of the ability of the plant to take carbon dioxide from the atmosphere. The compound of formula (Ic) is thus shown as being particularly suitable for closing the stomata and reducing transpiration of maize plants.

[0172] The results of Figure 10d show that the uptake of water of maize plants placed in drought conditions is reduced and delayed when the plant is treated with the compound of formula (Ic). Surprisingly, both the reduction and the delay are higher than when the plant is treated with ABA. The compound of formula (Ic) is thus shown as being particularly suitable for increasing the resistance of the plant to drought conditions, as the water needs of the plant are reduced. This is believed to be thanks to the closing of the stomata which allows the plant to retain water by minimizing transpiration and thus reducing water uptake from soil. RNA studies Gene expression in different plants was analyzed according to the following procedures:

[0173] Arabidopsis RNAseq: Arabidopsis seedlings grown for 10 days in MS liquid media were treated with 2.5 ^M of either ABA, opabactin or (Ic) in MS liquid media using 0.1% DMSO v / v in MS liquid media as control. Tissue was collected 6 hours after the treatment. RNA was extracted in quadruplicate and validated by qPCR. RNAseq analysis was carried out by BGI and data visualization with Dr. Tom (BGI).

[0174] The results of Figure 3 show that when Arabidopsis is treated with a compound of formula (Ic), genes associated to the response of ABA receptor agonism are expressed in a larger extent than when the plant is treated with ABA, or even with opabactin.

[0175] Tomato qPCR: 4 week-old tomato plants grown in a growth chamber were treated by spray with 10 ^M ABA, (Ic) in a water solution of 10mM MES pH 5.7, 0.02% silweet or 0.1% DMSO v / v in a water solution of 10mM MES pH 5.7, 0.02% silweet as control. Samples were collected 5 hours after the treatment. RNA extraction and cDNA synthesis was carried out using standard methods. qPCR was performed using previously reported primers for SlRAB18, SlLEA and SlEF1a (housekeeping).

[0176] The results of Figure 8 show that when a tomato plant is treated with a compound of formula (Ic), ABA responsive genes are expressed in a larger extent than when the plant is treated with ABA. This is particularly the case of SILEA gene, which regulates cold tolerance of the plant, as known in the art. This is also the case of SIRAB18 gene, which is an ABA-responsive gene.

[0177] Wheat qPCR: One week-old wheat plants grown in a growth chamber were treated by spray with 50 ^M ABA, (Ic) in a water solution of 10mM MES pH 5.7, 0.05% tween20 or 0.1% DMSO v / v in a water solution of 10mM MES pH 5.7, 0.05% tween20 as control. Samples were collected 12 hours after the treatment. RNA extraction and cDNA synthesis was carried out using standard methods. qPCR was performed using previously reported primers for TaAOS, and TaActin (housekeeping).

[0178] The results of Figure 9c show that when wheat plants are treated with a compound of formula (Ic), TaAOS gene is expressed in a larger extent than when the plant is treated with ABA or is untreated. As known in the art, the TaAOS gene in wheat is a gene activated by ABA..

Claims

CLAIMS 1. A compound of formula (I) or a salt, a solvate, a stereoisomer or a deuterated analogue thereofwherein: each of R1 and R2 is independently selected from the group consisting of hydrogen, a linear or branched (C1-C6)alkyl group and a (C3-C6)cycloalkyl group and provided that at least one of R1 and R2 is other than hydrogen; and Z is a radical selected from the radicals of formula (A) and (B)wherein: Y is selected from the group consisting of O, NR3, CHR3 and C(R3)2; and each R3 is independently selected from the group consisting of hydrogen, fluoro and a linear or branched (C1-C6)alkyl group that is optionally substituted with one or more fluorine atoms.

2. Compound of formula (I) according to claim 1 or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein each of R1 and R2 is independently selected from the group consisting of hydrogen, ethyl, propyl, isopropyl and a cyclopropyl group and provided that at least one of R1 and R2 is other than hydrogen.

3. Compound of formula (I) according to any one of claims 1 to 2 or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein one of R1 and R2 is hydrogen.

4. Compound of formula (I) according to any one of claims 1 to 3 or a salt, a solvate, a stereoisomer or a deuterated analogue thereof wherein Z is a radical of formula (A) wherein Y is a CHR3 group wherein R3 is selected from the group consisting of (C1- C3)alkyl and (C1-C3)perfluoroalkyl ; preferably R3 is selected from the group consisting of methyl and trifluoromethyl.or salts, solvates, stereoisomers or deuterated analogues thereof.

6. The compound of formula (I) according to claim 5 wherein the compound of formula (I) is selected from the compounds of formulae (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ih), (Ij), (Ik), (Il), (Im), (In), (Ip) and (It) or salts, solvates, stereoisomers or deuterated analogues thereof; preferably the compound of formula (I) is selected from the compounds of formulae (Ia), (Ib), (Ic), (If), (Ih), (Ij), (Ik), (Ip) and (It) or salts, solvates, stereoisomers or deuterated analogues thereof.

7. The compound of formula (I) according to any one of claims 5 to 6 wherein the compound of formula (I) is selected from the compounds of formulae (Ia), (Ib), (Ic), (Ij) and (It) or salts, solvates, stereoisomers or deuterated analogues thereof; preferably the compound of formula (I) is the compound of formula (Ic) or the compound of formula (It) or a salt, a solvate, a stereoisomer or a deuterated analogue thereof.

8. A process for the preparation of a compound of formula (I) as defined in any one of claims 1 to 7 comprising the step of contacting a compound of formula (II) with a compound of formula (III) in conditions sufficient for the formation of the compound of formula (I)wherein X is a halogen group and R1, R2and Z are as defined in any one of claims 1 to 7; preferably X is a chloride group.

9. The process according to claim 8 further comprising the previous step of preparing a compound of formula (II) by contacting a compound of formula (IV) with hydrazine in conditions sufficient for the formation of the compound of formula (II)wherein R1 and R2 are as defined in any one of claims 1 to 7.

10. The process according to claim 9 further comprising the previous step of preparing, in a first alternative, a compound of formula (IV) wherein one of R1 and R2 is hydrogen, said process comprising (i) contacting a compound of formula (Va) with a compound of formula R4- B(OH)2 or of formula R4-BF3K or of formula (C) in conditions sufficient for the formation of a compound of formula (IV);wherein each R4 is selected from a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a (C3-C6)cycloalkenyl and a (C3- C6)cycloalkyl group; the dashed bond represents the presence or absence of a covalent bond; when in the compound of formula (C) the dashed bond represents the absence of a covalent bond each of R4’ and R4’’ is independently selected from the group consisting of hydrogen and (C1-C6)alkyl group or, alternatively, R4’ and R4’’ together with the atoms to which they are attached form a 6 to 8-membered saturated or unsaturated ring, the members of said ring being selected from C,CH, CH2, B and O and said ring being further optionally substituted at any available position with a (C1-C6)alkyl group; and, when in the compound of formula (C) the dashed bond represents the presence of a covalent bond each of R4’ and R4’’ is independently hydrogen or a (C1-C6)alkyl group; or, alternatively, R4’ and R4’’ together with the atoms to which they are attached form a 3 to 8-membered aromatic, saturated or unsaturated ring, the members of said ring being selected from C, CH and CH2, and said ring being further optionally substituted at any available position with a (C1-C6)alkyl group; and (ii) when R4 is one of a linear or branched (C2-C6)alkenyl group or a (C3- C6)cycloalkenyl group, said process further comprises the step of converting the unsaturated R4 group of the product of step (i) in a saturated R4 group by catalytic hydrogenation; or, in a second alternative, a compound of formula (IV) wherein R1 and R2 are the same group and are other than hydrogen, said process comprising (i) contacting a compound of formula (Vb)with a compound of formula R4-B(OH)2 or of formula R4-BF3K or of formula (C) in conditions sufficient for the formation of a compound of formula (IV), said compounds being as defined in the first alternative and (ii) when R4 is one of a linear or branched (C2-C6)alkenyl group or a (C3- C6)cycloalkenyl group, said process further comprises the step of converting the unsaturated R4 groups of the product of step (i) in saturated R4 groups by catalytic hydrogenation; or, in a third alternative, a compound of formula (IV) wherein R1 and R2 are different groups and are other than hydrogen, said process comprising: (i) contacting a compound of formula (Va) a compound of formula R4-B(OH)2 or of formula R4-BF3K or of formula (C) in conditions sufficient for the formation of a compound of formula (IV), said compounds being as defined in the first alternative and;(ii) contacting the product of step (i) with a bromination agent such as N- bromosuccinimide so as to produce a compound of formula (VI)wherein R4 is selected from a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a (C3-C6)cycloalkenyl and a (C3-C6)cycloalkyl group; (iii) contacting a compound of formula (VI) a compound of formula R4-B(OH)2 or of formula R4-BF3K or of formula (C) in conditions sufficient for the formation of a compound of formula (IV), said compounds being as defined in the first alternative and; and (iv) when each R4 is one of a linear or branched (C2-C6)alkenyl group or a (C3- C6)cycloalkenyl group, said process further comprises the step of converting the unsaturated R4 groups of the product of step (iii) in saturated R4 groups by catalytic hydrogenation.

11. The process according to claim 10 further comprising the step of preparing a compound of formula (Va) or (Vb), said process comprising the step of contacting 4- ((1,3-dioxoisoindolin-2-yl)methyl)benzonitrile with a bromination agent such as N- bromosuccinimide in conditions sufficient for the formation of the compound of formula (Va) or (Vb), and wherein, preferably, when said step produces the compound of formula (Va) the molar amount of N-bromosuccinimide is of between 1 and 1,2 mole of N- bromosuccinimide per mole of 4-((1,3-dioxoisoindolin-2-yl)methyl)benzonitrile; or, alternatively, when said step produces the compound of formula (Vb) the molar amount of N-bromosuccinimide is of at least 2 moles of N-bromosuccinimide per mole of 4-((1,3- dioxoisoindolin-2-yl)methyl)benzonitrile.

12. The process according to claim 11 further comprising the step of preparing 4-((1,3- dioxoisoindolin-2-yl)methyl)benzonitrile, said process comprising contacting 4-(bromomethyl)benzonitrile with an alkaline phthalimide salt in conditions sufficient for the formation of 4-((1,3-dioxoisoindolin-2-yl)methyl)benzonitrile.

13. Agrochemical composition comprising the compound according to any one of claims 1 to 7 or a salt, a solvate, a stereoisomer or a deuterated analogue thereof, and an agrochemically acceptable carrier.

14. Use of the compound according to any one of claims 1 to 7 or a salt, a solvate, a stereoisomer or a deuterated analogue thereof or of the agrochemical composition according to claim 13 in one or more of: (i) enhancing abiotic stress resistance in a plant, (ii) inhibiting seed germination in a plant, and / or (iii) reducing leaf transpiration in a plant, said plant being preferably selected from the group consisting of Arabidopsis thaliana, tomato, wheat and maize and wherein, also preferably, said abiotic stress is drought.

15. Plant seed comprising or coated with the compound according to any one of claims 1 to 7 or a salt, a solvate, a stereoisomer or a deuterated analogue thereof or the agrochemical composition according to claim 13.

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