USE OF A SPECIFIC COMPOUND FOR THE DETECTION OF TOXIC CHEMICAL COMPOUNDS

Description

TECHNICAL FIELD

[0001] The present invention relates to the use of new specific compounds for the detection of organic compounds belonging to the category of toxic chemical compounds and, more specifically, to the category of organophosphorus compounds, sulfide compounds, amine compounds and arsenic compounds, these compounds being able to be toxic warfare compounds, pesticides, vesicants, toxic industrial chemical compounds (known as TIC).

[0002] In general, organophosphate compounds are organic compounds with proven toxicity to the human body. Indeed, these compounds can be involved in the inhibition of serine proteases, and in particular, acetylcholinesterase, which plays a role in synaptic junctions and whose dysregulation can prevent muscle relaxation and thus cause death by asphyxiation.

[0003] These compounds may be included in the formulation of insecticides, pesticides or chemical warfare agents (such as G-series organophosphate compounds, like sarin or V-series organophosphate compounds, like VX) and because of the high lethality of these compounds, their proliferation, it is important to have detection systems available.

[0004] Some detection systems used to date are based on technologies involving physical measurement methods, such as ion mobility spectroscopy, flame photometry, IR and Raman spectroscopies, with the difficulties that these systems require complex and expensive equipment that is not necessarily suitable for all intervention environments in terms of mass and size, in addition to the expertise of the operator to be taken into account.

[0005] In view of what exists, the authors of the present invention have turned to the discovery of new compounds usable for the detection of chemical compounds, such as organophosphorus compounds, with application both in liquid media and in supported media and allowing simple detection.

[0006] US patent 5,616,502 describes the use of a variety of merocyanine and substituted merocyanine dyes for detecting and quantifying poly(amino acids), including peptides, polypeptides, and proteins. The article by Gerhard J. Mohr, "New chromogenic and fluorogenic reagents and sensors for neutral and ionic analytes based on covalent bond formation - a review of recent developments," published in Analytical and Bioanalytical Chemistry, vol. 386, no. 5, pp. 1201-1214, describes new compounds for the detection of amines, diamines, amino acids, and proteins. DESCRIPTION OF THE INVENTION

[0007] The present invention is defined in the attached claims. The invention relates to the use of a compound comprising an aromatic group including at least one nitrogenous aromatic ring, which ring bearing at least two substituents conforming to the following formula (I): in which Ar denotes an aromatic group possibly substituted and the brace denotes the place by which the substituent is linked to the nitrogenous aromatic ring, said compound being used as a detection indicator for the detection of at least one chemical compound selected from organophosphorus compounds, sulfide compounds, amine compounds and arsenic compounds.

[0008] A detection indicator is classically understood to be a chemical compound capable of changing upon contact with at least one other chemical compound that one wishes to detect, this change being the sign of the presence of said at least one other chemical compound, this change materializing by a change of color, when the detection indicator is a colored indicator, which is the case for all or part of the compounds that are the subject of the use of the invention.More specifically, when the detection indicator is a colored indicator, it classically corresponds to a chemical compound that takes on at least one characteristic color in the presence of another chemical compound, or, in other words, a chemical compound that exhibits at least two colored states, one colored state existing when the chemical substance is not in the presence of the chemical compound to be detected and at least one other colored state when the chemical compound is in the presence of the chemical compound to be detected.

[0009] As mentioned above, the compound used, as a detection indicator, is a compound comprising at least one aromatic group including at least one nitrogenous aromatic ring, which ring being bearing at least two substituents, at least one of the substituents comprising a double bond conjugated with said ring.

[0010] More specifically, the compound may be a compound comprising, as an aromatic group including at least one nitrogenous aromatic ring, an aromatic group including a single nitrogenous aromatic ring.

[0011] More specifically, the compound may be a compound comprising, as an aromatic group including at least one nitrogenous aromatic ring, an aromatic group comprising, as a nitrogenous aromatic ring, a pyridine ring, which aromatic group may be a pyridine group as such (meaning, in other words; that the aromatic group consists of a single nitrogenous aromatic ring, which is a pyridine ring) or a quinoline group.

[0012] The nitrogenous aromatic ring may bear only two substituents, at least one of which includes a double bond conjugated with said ring and, preferably, two identical substituents, or alternatively two identical substituents each comprising a double bond conjugated with said ring.

[0013] Without being linked by theory, the nitrogenous aromatic ring is involved, to a large extent, in the detection of the compounds mentioned above, with a preference for disubstitution by conjugated parts which seems to be responsible for the large difference in color between the initial state of the compound and its final state after exposure to the compound to be detected, this conjugation being able to be generated by the presence of a double bond in the alpha position of the nitrogenous aromatic ring.

[0014] Ar designates an aromatic group, possibly substituted, and the brace designates the point at which the substituent is linked to the nitrogenous aromatic ring; this formula covers both isomeric forms trans that cis.

[0015] The aromatic group of all or part of the substituents and, in particular, Ar of formula (I) mentioned above, may be a monocyclic carbon aromatic group, for example, a phenyl group, or a monocyclic heteroaromatic group, for example, a monocyclic nitrogen heteroaromatic group, such as a pyridine group.

[0016] The aromatic group of all or part of the substituents and, in particular, Ar of formula (I) mentioned above, may optionally be substituted by one or more substituents, for example, chosen from an amine substituent (e.g., a primary amine -NH2, an alkylated tertiary amine, such as -N(CH3)2), an alkoxy substituent (e.g., -OCH3), a hydroxyl substituent -OH, a nitro substituent -NO2, a halogen substituent, a halogenated alkyl substituent (e.g., a perhaloalkyl substituent, such as -CF3), an ester substituent, such as -COOCH3, a carboxylic acid substituent -COOH, a cyano substituent -CN or an -S-alkyl substituent (e.g., -SCH3).

[0017] According to a particular embodiment of the invention, the compound may be a compound comprising, as an aromatic group including at least one nitrogenous aromatic ring, a quinoline group, the nitrogenous aromatic ring of the quinoline group bearing two identical substituents, each comprising a double bond conjugated with said ring and each comprising an aromatic group conjugated with said double bond. A compound of this type may correspond to the following formula (II): in which Ar denotes an aromatic group, more specifically, a monocyclic aromatic group, for example, a phenyl group or a pyridine group, the two substituents being able to be bonded to any of the free carbon atoms of the pyridine ring (namely, in this case, the positions ortho, meta Or para ) ,said aromatic group being optionally substituted by one or more substituents, for example, chosen from an amine substituent (e.g., a primary amine -NH2, an alkylated tertiary amine, such as -N(CH3)2), an alkoxy substituent (e.g., -OCH3), a hydroxyl substituent -OH, a nitro substituent -NO2, a halogen substituent, a halogenated alkyl substituent (by a perhaloalkyl substituent, such as -CF3), an ester substituent, such as -COOCH3, a carboxylic acid substituent -COOH, a cyano substituent -CN or an -S-alkyl substituent (e.g., -SCH3).

[0018] More specifically, a compound of this type can be a compound in which one of the substituents occupies the position ortho and the other substitute occupies the position para (relative to nitrogen), this compound thus corresponds to the following formula (III): with Ar being as defined above.

[0019] In particular, Ar can be a phenyl group substituted by an amine group and, more specifically, a tertiary amine group, such as -N(CH3)2 located, in particular, at position para, such a compound corresponding to the following formula (IV): this compound corresponding to 2,4- bis [p-(dimethylamino)styryl)quinoline.

[0020] The compounds used in the context of the invention can be purchased from a supplier or can be synthesized by conventional organic synthesis techniques involving, for example, coupling reactions, such as a Heck coupling, a Suzuki coupling, reactions involving the use of microwaves.

[0021] For example, when the compound corresponds to formula (IV) mentioned above, one synthetic route may consist of the formation of an intermediate compound in the form of a boronic acid followed by a Suzuki coupling as illustrated in the following diagram:

[0022] As mentioned above, the compounds used in the context of the invention serve as a detection indicator, in particular colorimetric, for the detection of a compound selected from organophosphorus compounds, sulfide compounds, amine compounds and arsenic compounds.

[0023] More specifically, compounds suitable for detection, particularly with the compound of formula (IV) mentioned above, may include: as organophosphate compounds, pesticides such as malathion, phosalone, trichlorfon, omethoate, fenthion, parathion, chlorpyrifos and methyl paraoxon or wartime toxic compounds such as sarin, tabun, methyl(1-(diethylamino)ethylidene phosphonamidofluoridate), ethyl(1-(diethylamino)ethylidene phosphoramidofluoridate), methyl (bis(diethylamino)methylene)phosphoramidofluoridate; as sulfide compounds, a wartime toxic compound such as sulfur mustard gas; as amine compounds, a wartime toxic compound such as nitrogen mustard gas; as arsenic compounds, wartime toxic compounds such as lewisite, diphenylchlorarsine, diphenylcyanoarsine.

[0024] The compounds used in the context of the invention for detection can be used in liquid phase or in supported phase.

[0025] When used in a supported phase, the support can be a paper support (such as chromatography paper), a non-woven fiber support (for example, a mixture of cellulose and polyester fibers), it being understood that the support must be suitable for impregnation by the compound retained for detection either directly or via particles previously impregnated with the compound selected for detection.

[0026] The aforementioned supports can be prepared by depositing the selected compound with a solution containing said compound, either using a micropipette or by printing (for example, via a Dimatix printer) or by screen printing application.

[0027] The aforementioned supports can also be prepared by depositing on a support a composition comprising particles previously impregnated with the detection indicator compound followed by drying of said composition.

[0028] The distinct types of particles can be inorganic particles, organic particles, or organic-inorganic hybrid particles, for example, so-called "core-bark" particles with an inorganic core and an organic bark.

[0029] Examples of inorganic particles include: of silica particles, in particular silica particles supplied by Aldrich under product reference 236802, these silica particles having an average pore size of 60 Å; of alumina particles; of zinc oxide particles; of titanium oxide particles; of diatomaceous earth particles; of zeolite particles; of geopolymer particles.

[0030] Examples of organic particles include polymeric particles, such as: of polyethylene particles, in particular, polyethylene particles supplied by Aldrich under product reference 434264, these polyethylene particles having an average particle size of 180 µm or polyethylene particles supplied by Alfa under product reference A10239 having an average particle size of 500 µm or polyethylene particles supplied by Mitsui Chemicals under product reference MIPELON XM220 having an average particle size of 30 µm; of polyamide particles, such as nylon particles, in particular, nylon-6 particles supplied by Aldrich under product reference GF58818471 having an average particle size ranging from 5 to 50 µm or nylon-12 particles supplied by Aldrich under product reference GF33201098 having an average particle size ranging from 10 to 50 µm; of starch particles.

[0031] Finally, the invention also relates to a method for detecting the presence or absence of at least one chemical compound chosen from organophosphorus compounds, sulfide compounds, amine compounds and arsenic compounds comprising the following steps: a step of bringing into contact the medium(s), in which the presence or absence of said chemical compound(s) is to be detected, with a detection indicator which is a compound as defined above; a step of deduction, based on the possible transformation signal(s) of the detection indicator, of the presence or absence of said compound(s), this or these transformation signal(s) being classically a chromatic change.

[0032] This contact step may consist of depositing on the surface of the detection system one or more separate drops of each medium whose absence or presence of one or more chemical compounds we want to analyze.

[0033] It is understood that the compound to be used in the aforementioned process must be capable of detecting the chemical compound(s) whose absence or presence is to be determined.

[0034] Between the contact stage and the deduction stage, a waiting period may be provided so that, if necessary, the color change can take place.

[0035] Regarding the deduction step, when the transformation signal(s) classically consist of a chromatic change, the operator can rely on a colorimetric scale associated with the compound acting as a detection indicator, which will define, for all chemical compounds likely to be detected by the system, the corresponding chromatic change, this colorimetric scale being able to be determined, by prior tests, for the detection indicator and the chemical compounds intended to be detected by said indicator.

[0036] Other features and advantages of the invention will become more apparent upon reading the following supplementary description, which includes examples of detection in accordance with the invention.

[0037] Of course, the following examples are given only as an illustration of the object of the invention and do not in any way constitute a limitation of this object. DETAILED DESCRIPTION OF SPECIFIC METHODS OF IMPLEMENTATION EXAMPLE 1

[0038] This example illustrates the preparation of a specific compound usable within the scope of the invention, the 2-4 -bis [p-(dimethylamino)styryl]quinoline corresponding to the following formula: This compound is prepared by the steps summarized in the following diagram:

[0039] The detailed protocol is as follows.

[0040] 4-Ethynyl-N,N-Dimethylaniline (290.4 mg, 2 mmol) is dissolved in 20 mL of THF. The solution is degassed with argon and placed under an inert atmosphere. A 1 M catecholborane solution in THF (2.4 mL, 2.4 mmol) is added to the mixture, and the reaction is refluxed (60°C) for 1.5 hours. A second portion of catecholborane (1.6 mL, 1.6 mmol) is added, and the reaction is stirred under reflux for an additional 2 hours. The mixture is cooled to room temperature (25°C), and 2,4-Dibromoquinoline (229.6 mg, 2 mmol) and the catalyst Pd(PPh3)4 (462.2 mg, 0.4 mmol) are added directly to the reaction mixture under magnetic stirring. After 20 minutes, a 20% aqueous solution of K₂CO₃ (1 mL) is added and the reaction is refluxed for a total reaction time of 18 hours under an inert atmosphere (Ar). After this time, the mixture is cooled to room temperature and 5 mL of deionized water is added.The compound is extracted with ethyl acetate (2 x 10 mL). The organic phases are combined, washed with water (2 x 10 mL) and sodium chloride brine (10 mL), and dried over MgSO4. Excess solvent is removed by evaporation, and the compound is purified by silica column chromatography. EXAMPLE 2

[0041] This example illustrates the implementation of the compound prepared in example 1 for the liquid phase detection of organophosphate or organothiophosphate pesticide compounds.

[0042] To do this, the 2.4- bis-The [p-(dimethylamino)styryl]quinoline prepared in Example 1 is solubilized to 10 mM in DMSO. The molecule thus takes on a yellow color initially. The pesticides, on the other hand, are solubilized to 0.267 M. The exposure phase consists of taking 2.5 µL of the 2,4-bis[p-(dimethylamino)styryl]quinoline solution, diluting this volume with 10 µL of DMSO, and adding 37.5 µL of the solution of a given pesticide. Thus, the 2,4- bis [p-(dimethylamino)styryl]quinoline is found in a final volume of 50 µL of DMSO, concentrated to 0.5 mM in the presence of 400 pesticide equivalents (at the final concentration of 0.01 mM). The 2,4- bis [p-(dimethylamino)styryl]quinoline was thus exposed to 8 pesticides: Malathion, Phosalone, Trichlorfon, Omethoate, Fenthion, Parathion, Chlorpyrifos and paraoxon methyl.

[0043] It appears that the 2.4- bis[p-(dimethylamino)styryl]quinoline undergoes a colorimetric change visible to the naked eye for all pesticides tested with kinetics depending on the pesticides, the kinetics being notably faster with malathion and trichlorfon. EXAMPLE 3

[0044] This example illustrates the implementation of the compound prepared in Example 1 for the liquid-phase detection of toxic warfare compounds.

[0045] To do this, 100 µL of 2,4- bis [p-dimethylamino)styryl]-quinoline in solution at 1 mmol / L in DMSO is deposited using a multichannel electronic pipette into wells of a polystyrene plate.

[0046] Five chemical warfare agents (Sarin (known as GB, CAS No. 107-44-8), Tabun (known as GA, CAS No. 77-81-6), Sulphur Mustard (known as HD, CAS No. 505-60-2), Nitrogen Mustard (known as HN3, CAS No. 555-71-1), and Lewisite (known as L1, CAS No. 541-25-3)) are deposited in separate wells as drops using a multichannel electronic pipette. The volumes of agents deposited are calculated such that, for 1 molar equivalent of 2.4- bis [p-dimethylamino)styryl]-quinoline, 400 molar equivalents of toxic substance are added. Scans are performed at 5 min to be compared to a scan of a control (i.e., the well containing only the 2,4- solution). bis [p-dimethylamino)styryl]-quinoline).

[0047] In the liquid phase in solution in DMSO, the 2,4 -bis[p-dimethylamino)styryl]-quinoline changes color radically in 5 minutes, from yellow to black, for the five toxic warfare compounds tested (Sarin, Tabun, Sulphurous Mustard (HD), Nitrogenous Mustard (HN3), Lewisite (L1)). EXAMPLE 4

[0048] This example illustrates the implementation of the compound prepared in example 1 for the supported phase detection of organophosphorus pesticide compounds.

[0049] More specifically, two support prototypes were produced by "spotting" (more specifically, here, by liquid deposition of 13 separate drops of the specific compound previously solubilized at 10 mmol / L in DMSO using a multi-channel electronic pipette followed by drying of said drops), respectively, a chromatography paper (made of Grade 4 Chr cellulose, 460*570 mm and a thickness of 0.21 mm) and a non-woven fiber wipe (polyester and cellulose fibers Spec-Wipe 3 300*300 mm).

[0050] The two supports thus covered with 13 distinct drops are exposed to 12 pesticides (1 drop of distinct pesticide for one drop of compound from example 1, the thirteenth drop not being exposed to serve as a control), the 12 pesticides being the following: Malathion, Phosalone, Trichlorfon, Omethoate, Fenthion, Parathion, Chlorpyrifos, Paraoxon Methyl, dimethoate, dichlorvos and diazinon.

[0051] More specifically, each pesticide is first solubilized at 100 mmol / L in DMSO before being deposited, and then the pesticides are deposited at a rate of 1.2 µL via a multichannel electronic pipette so as to expose, within a drop of compound of example 1, said compound to 10 equivalents of pesticide compound.

[0052] The two substrates are then scanned after 5 minutes, 1 hour and 72 hours after exposure to pesticides.

[0053] At the end of the 72 hours, the color change occurred for each of the pesticides (change from yellow brown to brown) for both supports, with a more marked change for the non-woven fiber wipe. EXAMPLE 5

[0054] This example illustrates the implementation of the compound prepared in Example 1 for the supported phase detection of toxic warfare compounds.

[0055] More specifically, two substrate prototypes were produced using inkjet printing on a DIMATIX printer: one made of non-woven fibers (polyester and cellulose fibers) and the other of polyolefin. To do this, the 2.4- bis[p-Dimethylamino)styryl]-quinoline is solubilized at 100 mM in DMSO. Printing is performed using a Dimatix DMP 2800 series inkjet printer (Fujifilm). The printing patterns are 8 mm diameter cells, designed to print droplets spaced 150 µm apart. This 150 µm spacing allows for maximum dot density, and therefore maximum color density. In our case, one-third of the droplets occupy one-third of the surface area, with the remaining two-thirds of the surface unprinted.

[0056] The two supports thus covered with cells (11 in total) are exposed to 10 toxic warfare compounds (1 drop of distinct toxic warfare compound per distinct cell, the eleventh cell not being exposed to serve as a control), the 10 toxic warfare compounds being the following: Sarin, Tabun, methyl(1-(diethylamino)ethylidene phosphonamidofluoridate), ethyl(1-(diethylamino)ethylidene) phosphoramidofluoridate, ( bis (diethylamino)methylene)methyl phosphoramidofluoridate, Sulphur mustard (HD), Nitrogen mustard (HN3), Lewisite (L1), diphenylchlorarsine (C1), diphenylcyanoarsine (C2).

[0057] Regardless of the support, a color change is observed in the alveoli after 5 minutes of exposure for each of the toxic warfare compounds. EXAMPLE 6

[0058] This example illustrates the preparation of silica particles impregnated with 2,4- bis[p-dimethylamino)styryl]quinoline according to the following operating protocol: 1) Weigh the powder in a round-bottom flask; 2) Weigh the required amount of quinoline compound (0.1% by mass relative to the powder mass) into a pillbox; 3) Add a solvent to the pillbox to dissolve the compound and achieve a concentration of approximately 30 mg / mL; 4) Pour the compound solution over the powder in the flask and rinse the pillbox several times, then add the rinsing solvent to the flask; 5) Depending on the appearance of the powder in the flask, add as much solvent as necessary to wet and suspend the powder; 6) Evaporate in three stages: *Rotate the rotary evaporator in a water bath (55°C) for 10 minutes to homogenize the suspension in the flask and raise the temperature; *Slowly reduce the pressure to 400 mbar to slowly distill off the solvent;*When the powder begins to clump together to form a ring that attaches to the wall of the balloon, the pressure drops more rapidly until it is completely dry.

[0059] The impregnated powder thus obtained is incorporated into a solution obtained according to the following procedure: 1°) Preparation of a 30% mass polystyrene-b-poly(ethylene-ran-butylene)-b-polystyrene block copolymer solution (PSPEPB) in cyclohexane; 2°) Weighing decane in a glass bottle; 3°) Adding the required mass of PSPEPB solution; 4°) Adding the required mass of impregnated powders to the bottle; 5°) Mixing by vortex stirring and ultrasonics if necessary.

[0060] The table below illustrates, more precisely, the mass proportions of these ingredients according to the nature of the powder used. Powder Composition Silica 30% impregnated powder, 9.6% PSPEPB, 22.4% cyclohexane, 38% decane

[0061] The composition is then deposited onto a chromatography paper substrate by coating with a squeegee, and more specifically, using an Elcometer 4340 semi-automatic squeegee tool. via the following operations: setting the speed of the squeegee to the minimum (position 1 out of the 11 possible positions); fixing the substrate on the metal table of the tool; manually depositing a bead of the particle composition in front of the squeegee with the polypropylene Pasteur pipette; driving the squeegee at the programmed speed by the moving gantry; detaching the substrate and then drying under a fume hood.

[0062] The substrate thus obtained is then subjected to 12 toxic compounds, each deposited at a rate of 1.6 µL via A multichannel electronic pipette is used, with the sample placed in individual wells provided on the support. The support is then scanned after 5 minutes and again after 1 hour of exposure to the toxic compounds.

[0063] The 12 toxic compounds are organophosphate compounds of the G series (Sarin, Soman and Tabun), one organophosphate compound of the V series (VX, CAS No. 50782-69-9), vesicants (sulfur mustard gas, nitrogen mustard gas, lewisite), arsenic compounds (diphenylchlorarsine known as "C1" and diphenylcyanoarsine known as "C2") and the following organophosphate compounds: methyl(1-(diethylamino)ethylidene phosphonamidofluoridate), methyl(1-(diethylamino)ethylidene phosphoramidofluoridate), ethyl(1-(diethylamino)ethylidene phosphoramidofluoridate).

[0064] The aforementioned substrate allows the detection of the 12 toxic compounds in the following manner: by the appearance of a darker color (burgundy brown) on contact with toxic compounds (Tabun, Sulphurous Mustard (HD), Nitrogenous Mustard (HN3), diphenylcyanoarsine (C2)); by lightening towards yellow on contact with toxic compounds (VX, methyl(1-(diethylamino)ethylidene phosphoramidofluoridate), methyl(1-(diethylamino)ethylidene phosphonamidofluoridate), ethyl(1-(diethylamino)ethylidene phosphoramidofluoridate), Lewisite (L1), diphenylchlorarsine (C1)); or by a slight change from the initial color on contact with toxic compounds (Sarin, Soman).

[0065] Tests were also carried out with polyamide-6, polyamide-12, polyethylene, and silica functionalized with amine groups, with conclusive results also obtained for the 12 aforementioned toxic compounds.

Claims

1. Use of a compound comprising an aromatic group comprising at least one nitrogenous aromatic cycle, which cycle carries two identical substituents which correspond to the following formula (I): wherein Ar denotes an optionally substituted aromatic group and the bracket indicates the position at which the substituent is bonded to the nitrogenous aromatic cycle, said compound being used as a detection indicator for the detection of at least one chemical compound selected from organophosphate compounds, sulphide compounds, amine compounds and arsenic-containing compounds.

2. Use according to claim 1, wherein the compound comprises, as an aromatic group comprising at least one nitrogenous aromatic cycle, an aromatic group comprising a single nitrogenous aromatic cycle.

3. Use according to claim 1 or 2, wherein the compound comprises, as an aromatic group comprising at least one nitrogenous aromatic cycle, an aromatic group comprising, as a nitrogenous aromatic cycle, a pyridine cycle.

4. Use according to any one of the preceding claims, wherein the aromatic group is a pyridine group or a quinoline group.

5. Use according to any one of claims 1 to 4, wherein the aromatic group Ar is a carbonated monocyclic aromatic group, preferably a phenyl group.

6. Use according to any one of claims 1 to 4, wherein the aromatic group Ar is a monocyclic heteroaromatic group.

7. Use according to claim 6, wherein the aromatic group Ar is a monocyclic nitrogenous heteroaromatic group, preferably a pyridine group.

8. Use according to any one of claims 1 to 7, wherein the aromatic group Ar is substituted with one or more substituents.

9. Use according to claim 8, wherein the substituent(s) is / are selected from an amine substituent, an alkoxy substituent, a hydroxyl substituent -OH , a nitro substituent -NO2, a halogen substituent, a halogenated alkyl substituent, an ester substituent, a carboxylic acid substituent -COOH, a cyano substituent -CN, or an - S-alkyl substituent.

10. Use according to claim 1, wherein the compound is a compound comprising, as an aromatic group comprising at least one nitrogenous aromatic cycle, a quinoline group, the nitrogenous aromatic cycle of the quinoline group carrying two identical substituents, each comprising a double bond conjugated with said cycle and each comprising an aromatic group conjugated with said double bond.

11. Use according to any one of claims 1 to 4, wherein the compound complies with the following formula (II): wherein Ar denotes an aromatic group optionally substituted by a group chosen from an amine substituent, an alkoxy substituent, a hydroxyl substituent - OH, a nitro substituent -NO2 , a halogen substituent, a halogenated alkyl substituent, an ester substituent, a carboxylic acid substituent -COOH, a cyano substituent -CN or an -S-alkyl substituent.

12. Use according to claim 11, wherein the compound complies with the following formula (III): with Ar being as defined in claim 11.

13. Use according to claim 11 or 12, wherein the compound complies with the following formula (IV):

14. Use according to any one of the preceding claims, wherein the compound used as a detection indicator is used in the liquid phase or supported phase.

15. Method for detecting the presence or absence of at least one chemical compound selected from organophosphate compounds, sulphide compounds, amine compounds and arsenic-containing compounds comprising the following steps: - a step of placing the medium / media in contact, it being desirable to detect the presence or absence of said chemical compound(s) therein with a detection indicator which is a compound as defined according to any one of claims 1 to 14; - a step of deducing, according to the possible transformation signal(s) of the detection indicator, the presence or absence of said compound(s).