EP2877000A1 - Phytosanitary compositions comprising an ether-amide compound - Google Patents

Abstract

The subject matter of the present invention is phytosanitary compositions comprising an active phytosanitary product and an ether-amide compound. The ether-amide compound may in particular be present as a solvent, co-solvent, crystallization inhibitor or agent for increasing the bioactivity of the active phytosanitary product.

Description

 Phytosanitary compositions comprising an ether-amide compound

The present invention relates to phytosanitary compositions comprising an active plant protection product and an ether-amide compound. The ether-amide compound may in particular be present as a solvent, co-solvent, crystallization inhibitor or agent for increasing the bioactivity of the active plant protection product.

 Agriculture uses many active ingredients such as fertilizers or pesticides, for example insecticides, herbicides or fungicides. We talk about active plant protection products (or active ingredient). Active plant protection products are usually produced in pure or highly concentrated form. However, they must be used on farms at low concentrations. For this purpose, they are usually formulated with other ingredients to allow easy weight dilution by the farmer. We speak of phytosanitary formulations. The dilution carried out by the farmer is generally carried out by mixing the phytosanitary formulation with water.

 Thus the phytosanitary formulations must allow easy weight dilution by the farmer, in order to obtain a product in which the phytosanitary product is correctly dispersed, for example in the form of a solution, emulsion, suspension, or suspension. emulsion. For example solvents may be used for the formulation of active plant protection products, for example in the form of emulsifiable concentrates (Emulsifiable Concentrate "EC") intended to be diluted in water by the farmer, before application to a field.

 The phytosanitary formulations thus allow the transport of a phytosanitary product in relatively concentrated form, easy packaging and / or easy handling for the end user.

Some solid phytosanitary assets are often difficult to formulate. This is for example the case of tebuconazole, which is a particularly effective fungicide, and widespread use, especially for soybean cultivation. For certain phytosanitary actives, it is difficult to produce concentrated formulations that are easy to dilute for the farmer, that are stable and that have no (proven or perceived) substantial safety, toxicity and / or eco-toxicity disadvantages. For some assets, it is difficult to formulate at relatively high concentrations, with sufficient stability. In particular it is necessary to avoid the appearance of crystals in particularly at low temperature and / or during dilution and / or during storage at high temperature of the diluted composition. The crystals can have negative effects, including clogging the filters of the devices used to spread the diluted composition, clog the spraying devices, reduce the overall activity of the formulation, create unnecessary problems of waste streams to eliminate the crystals, and / or cause a bad distribution of the active product on the agricultural field.

 The industry is looking for compounds that may have solvent properties and to vary or optimize phytosanitary formulations. In particular, the industry needs low cost compounds with interesting properties of use. The industry also needs compounds with a toxicological and / or ecotoxicological profile perceived as favorable, including low volatility (low VOC), good biodegradability, low toxicity and / or low hazard.

The use as solvents of dialkylamides is known. These are products of formula R-CONMe ₂ where R is a hydrocarbon group such as an alkyl, typically C ₆ -C ₃ o. Such products are in particular marketed under the name Genagen® by the company Clariant. These solvents find applications particularly in the phytosanitary field. These solvents, however, have a limited range of use and do not allow solubilizing certain phytosanitary actives at certain concentrations, in useful temperature ranges, without crystal formation. They are also generated from an expensive raw material.

 There remains a need for new phytosanitary formulations, in particular phytosanitary formulations with relatively high concentrations of active plant protection products, which may have good stability, for example by reducing or even preventing the formation of crystals, especially at low temperatures and / or or during the dilution and / or storage at high temperature of the diluted composition.

 The present invention aims to meet at least one of the needs expressed above and it achieves this by the implementation of a particular ether-amide compound.

Thus, the present invention relates, according to one of its aspects, to a phytosanitary formulation comprising at least:

(a) an active plant protection product, b) a compound of formula (I) below:

R ^a R ^b C (OR) -AC (O) -NR ² R ³ (I)

 in which :

- R ^a and R ^b , identical or different, are groups selected from hydrogen atom and linear or branched alkyl groups, especially CC ₆ ;

 - R is a hydrocarbon group comprising an average number of carbon atoms ranging from 1 to 36, saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic, optionally substituted;

R ² and R ³ , which are identical or different, are groups chosen from a hydrogen atom and hydrocarbon groups comprising an average number of carbon atoms ranging from 1 to 36, saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic, optionally substituted, R ² and R ³ may optionally form together a ring comprising the nitrogen atom to which they are bonded, optionally substituted and / or optionally comprising an additional heteroatom,

 - A represents a linear or branched alkyl group, the main chain comprises at least 2 carbon atoms;

 c) optionally a surfactant, and

 d) possibly water.

 The invention also relates, in another of its aspects, the use of a compound of formula (I) according to the invention in phytosanitary formulations comprising a), optionally c) and optionally d).

 The invention also relates, in another of its aspects, to the use of a compound of formula (I) according to the invention in phytosanitary formulations comprising a), optionally c) and optionally d), as a solvent, co-solvent, crystallization inhibitor, and / or agent for increasing the bioactivity of said active plant protection product.

 The invention also relates, in another of its aspects, to a process for preparing phytosanitary formulations comprising a step of mixing a), b), optionally c), and optionally d).

The invention also relates to the use of a phytosanitary formulation according to the invention for treating agricultural surfaces as well as a method for treating agricultural surfaces comprising at least one step of applying a phytosanitary formulation according to the invention, in general in diluted form. Definitions

 In the context of the present invention, we mean by:

 "compound of the invention", a compound of formula (I) according to the invention;

 "Composition of matter" means a more or less complex composition comprising several chemical compounds. It can typically be an unpurified or modestly purified reaction product.

 For example, the compound of the invention may in particular be isolated and / or marketed and / or used in the form of a composition of matter comprising it. The compound of the invention, in the form of a pure molecule or in the form of a mixture corresponding to formula (I), can thus be included in a composition of matter within the meaning of the invention.

 Furthermore, in the context of the present invention, the term "solvent" is understood in a broad sense, covering in particular the functions of co-solvent and crystallization inhibitor.

 The term "solvent" can in particular designate a liquid product at the temperature of use, preferably with a melting point of less than or equal to 20 ° C., preferably at δ'Ό, preferably at 0 ° C., which can contribute to making a liquid solid material, to make a liquid material more fluid, or to prevent or retard the solidification or crystallization of material in a liquid medium.

Phytosanitary formulations

 For the purposes of the invention, a phytosanitary formulation is a phytosanitary formulation, preferably concentrated, comprising at least one active compound.

 By "concentrated" is meant a formulation whose weight concentration of the active is between 10% and 80% relative to the total weight of the formulation.

 The phytosanitary formulation of the invention is preferably in liquid form.

Different types of phytosanitary formulations can be implemented, in particular according to the different phytosanitary products. Examples are emulsifiable concentrates (Emulsifiable Concentrates "EC"), soluble concentrates (Soluble Concentrate "SL"), concentrated emulsions (Emulsion in water "EW"), microemulsions ("ME"), wettable powders ( Wettable Powders "WP"), Water Dispersible Granules ("WDG"), Suspo-Emulsions ("SE"). The formulations may depend on the physical form of the phytosanitary product (for example solid or liquid), and its Physico-chemical properties in the presence of other compounds such as water or non-aqueous dispersion, emulsification or solubilization media.

 After dilution by weight by the farmer, for example by mixing with water, the phytosanitary product may be in various physical forms: solution, dispersion of solid particles, dispersion of droplets of the product, droplets of solvent in which the product is dissolved.

The formulation of the invention can notably present:

 a solubilization of large amounts of active ingredients,

 a lack of crystallization, even under demanding conditions,

an increase in the biological activity that may be due to a good solvation, and / or

 - a safety profile, toxicology and / or eco-toxicology perceived as favorable.

 Details about products a), b), c), and d) are given below. Compound b) of formula (I)

 Compound b) has the general formula (I) given above. It is noted that it may be a mixture of several compounds of general formula (I). In other words the compound can be alone or in mixture. In the case of mixtures of several compounds, the number of atoms or of units can be expressed in average number. These are average numbers in number. In the case of single compounds, it will generally be integers, as regards the number of carbon atoms.

The groups R ^a and R ^b , which are identical or different, are groups selected from hydrogen atom and linear or branched alkyl groups. The alkyls may in particular be C 1 -C ₆ alkyls, preferably C 1 -C 3 alkyls. It may especially be methyl or ethyl groups.

According to a particular embodiment, at least one of the groups chosen from R ^a and R ^b is different from the hydrogen atom, for example a group chosen from linear or branched alkyl groups. The alkyls may in particular be C 1 -C ₆ alkyls, preferably C 1 -C 3 alkyls. || may especially be methyl or ethyl groups.

 According to particular embodiments:

- R ^a = H and R ^b = H, or

- R ^a = -CH ₃ and R ^b = H, or - R ^a = -C ₂ H ₅ and R ^b = H.

According to a particular embodiment, the total number of carbon atoms in compound b), excluding groups R ¹ , R ² and R ³ , is 4, 5, 6, 7 or 8, or average numbers between each of these values.

Group A represents a linear or branched alkyl group, the main chain of which comprises at least 2 carbon atoms.

 For the purposes of the invention, the term "main chain" is intended to denote the hydrocarbon chain connecting the carbon atom carrying the amide function and the carbon atom carrying the ether function, these two carbon atoms being excluded.

 According to one embodiment, the group A represents a linear or branched alkyl group whose main chain comprises at least 2 carbon atoms, for example from 2 to 8 carbon atoms, for example from 2 to 6 carbon atoms, preferably from 2 to 4 carbon atoms.

 According to one embodiment, the group A represents a linear alkyl group.

 In another embodiment, the group A represents a branched alkyl group.

 In this case, it may be an alkyl group branched by at least one alkyl group, itself linear or branched, comprising from 1 to 10 carbon atoms, for example from 2 to 8 carbon atoms. It may especially be ethyl or methyl groups.

The groups R ² and R ³ , which are identical or different, are groups chosen from a hydrogen atom and hydrocarbon groups comprising an average number of carbon atoms ranging from 1 to 36, saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic, optionally substituted, R ² and R ³ may optionally together form a ring comprising the nitrogen atom to which they are bonded, optionally substituted and / or optionally comprising an additional heteroatom. It should be noted that R ² and R ³ are not simultaneously hydrogen atoms. In other words the group - CONR ² R ³ is not a group -CONH ₂ . It may be a -CONHR ² group in which R ² is not a hydrogen atom, or a -CONR ² R ^{3 group in} which R ² and R ³ are not hydrogen atoms.

R ² and R ³ , which may be identical or different, may for example be chosen from methyl, ethyl, propyl (n-propyl), isopropyl, n-butyl and isobutyl groups, n- pentyl, amyl, isoamyl, hexyl, cyclohexyl, mixtures thereof and / or combinations thereof. R ² and R ³ may also be such that together they form with the nitrogen atom a morpholine, pyrrolidine, piperazine or piperidine group.

According to a preferred embodiment, R ² and R ³ are both methyl groups.

The group R ¹ is a hydrocarbon group comprising an average number of carbon atoms ranging from 1 to 36, in particular from 1 to 25, in particular from 1 to 20, saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic, optionally substituted.

 It can especially be a hydrocarbon group selected from methyl, ethyl, propyl (n-propyl), isopropyl, n-butyl, isobutyl, n-pentyl, amyl, isoamyl, hexyl, or cyclohexyl.

 According to one embodiment, R1 is chosen from a methyl group and a methyl group.

According to a particular embodiment R ^a = R ^b = H and R ¹ is an alkyl group comprising less than 10 carbon atoms, for example less than 5 carbon atoms, for example a methyl or ethyl group.

According to another embodiment R ^a = -CH ₃ or C ₂ H ₅ , R ^b = H and R ¹ is an alkyl group comprising less than 10 carbon atoms, for example less than 5 carbon atoms, for example a group methyl or ethyl.

According to one embodiment, the compound of the invention can be completely miscible in water.

 According to a particular embodiment, the compound of the invention is partially miscible in water. The miscibility in water may for example be less than 10% by weight (at 25 ° C), preferably 2%, preferably 1% or 0.1%. It may be greater than 0.001%, preferably 0.01% or 0.1%. It may for example be between 0.01% and 2%, for example between 0.1% and 1%.

Surprisingly, the compounds of the invention have good solvent properties, especially for phytosanitary actives in phytosanitary formulations with low miscibility in water. The groups R ^a , R ^b , A and / or the group R ¹ and / or the groups R ² and R ³ may be chosen so as to control the miscibility in water. In the case where the compound is miscible with water may advantageously combine the compound of formula (I) with a co-solvent. Details of co-solvents are given below.

The compound of the invention may in particular have one of the following formulas:

CH ₃ 0-CH ₂ -CH ₂ -CH ₂ -CONMe ₂

CH ₃ 0-CH ₂ -CH ₂ -CH ₂ -CH ₂ -CONMe ₂

CH ₃ 0-CH ₂ -CH ₂ -CH ₂ -CH ₂ -CH ₂ -CONMe ₂

C ₂ H ₅ 0-CH ₂ -CH ₂ -CH ₂ -CONMe ₂

C ₂ H ₅ 0-CH ₂ -CH ₂ -CH ₂ -CH ₂ -CONMe ₂

C ₂ H ₅ 0-CH ₂ -CH ₂ -CH ₂ -CH ₂ -CH ₂ -CONMe ₂

It is mentioned that the compound of the invention may be included in a composition of matter, comprising products other than the compound alone or in a mixture of formula (I). In the composition of matter the compound of the invention may represent at least 10% by weight. Preferably, it is the main compound of the composition of matter. The term "main compound" as used herein means the compound whose content is the highest, even if its content is less than 50% by weight (for example in a mixture of 40% A, 30% B, and 30% of C, product A is the main compound). Even more preferably the compound of the invention is at least 50% by weight of the composition of matter, for example 70% to 95% by weight, and even 75% to 90% by weight. As indicated above, the composition of matter can be a reaction product. The other products of the composition of matter may in particular be by-products of impurities, unreacted products, or products corresponding to reaction adducts of products included in the starting compounds not leading to compounds of formula (I).

Process

 The compound of the invention may be prepared by any suitable method.

 These compounds can be synthesized by the following synthetic routes:

- reaction between lactones and amino required to form the corresponding amido alcohols according to procedures known to the skilled person (see in particular the references in Comprehensive Organic Transformations, ^2nd Edition, Richard C. Larock, page 1973 - 1976 , or

- etherification reaction of the alcohol function of amidoalcool previously formed according to procedures known to the skilled person (see in particular the references in Comprehensive Organic Transformations, ^2nd Edition, Richard C. Larock, page 890 - 898.

Active plant protection product a)

 Active plant protection products, especially non-water soluble and solid products are known to those skilled in the art. The active plant protection product may in particular be a herbicide, an insecticide, an acaricide, a fungicide, a nematicide, a miticide, a mollusquicide, an antimicrobic agent, or a rodenticide elimination agent ("rodenticide" in English), for example a rodenticide.

 It is noted that the phytosanitary formulation may comprise several different active plant protection products.

 By way of nonlimiting examples of suitable active ingredients, mention may be made, inter alia, of the products of the following groups:

Acetamide Diphenyl ether Phosphinic acid Acideity regulator Diphenyl ether, sodium Phosphonoglycine Acylalanine Diphenyl oxazoline Phosphonothioate Aldehyde Dithiocarbamate Phosphoramidate Aliphatic ketone Ethylene generator Phosphorodithioate Alkanamide Fenanilide Phosphorothiolate Alkane hydrocarbon Formamidine Phosphorothiolate Alkyl iodide Furamide Phthalamate

Alkylamine Furanilide Phthalimide Alkylchlorophenoxy Glycine derivative Piperazine

Amide Guanidine Piperidine

 Amidine Halogenated aliphatic Polycyclic aromatic ketone

Amine Halogenated Aliphatic Carbohydrate Polysaccharide

Anilide compound Pryimidinamine

 Anilinopyrimidine Halogenated alkane Pyrazole

 Anthranilic diamide Halogenated hydrocarbon Pyrazolone

 Aromatic carboxylic acid Heteroaramatic Pyrethroid

 Aromatic hydrocarbon Hydrazine carboxylate Pyrethroid (diasterioisomer

Aryaminopropionic acid Hydrocarbon mixture)

 Aryl triazolinone Hydrocoumarin Pyrethroid ester

 Arylalanine Hydroxyanilide Pyrethroid, isomer mixture

Aryloxyalkanoic acid Hydroxybenzonitrile Pyridazine

 Aryloxyphenoxypropionate Hydroxycoumarin Pyridazinone

 Aryloxyphenoxypropionic Imidazole Pyridine

Imidazolinone acid Pyridine carboxylic acid

Arylpyrrole Indandione Anticoagulant Pyridine Compound

Auxin Inert Solvent Pyrimidine

 Avermectin Inorganic Compound Pyrimidine

 Benonorbene Inorganic metal oxide Pyrimidinol

 Benzamide Isomeric amine of pyridine Pyrimidinyl carbinol

 Benzanilide Isothiazolone Pyrimidinyl carboxy compound

Benzenamine Isoxazole Pyrimidinyloxybenzoic

Benzene-dicarboxamide Isoxazolidinone Pyrimidinyloxybenzoic

Benzenedicarboxylic acid Juvenile analogue analogue hormone

 Benzilate Juvenile hormone mimic Pyrimidinylsulfonylurea

Benzothiadiazole Juvenile hormone mimic Quarternary ammonium

Benzothiazole (terpene) Quinazinalone

 Benzoylphenyl urea Malonanilate Quinazolinone

 Benzoylurea Mandelamide Quinoline

 Biopesticide Mercaptobenzothiazole Quinolinecarboxylic acid

Biopesticide - Methylthiotriazine nactins Quinolone

 Bipyridylium Methylthiotriazine Quinone

 Bis-Carbamate Mix of 3'0-ethyl-5,6- Saturated fatty acid

 dihydrospinosyn / 3'-O-ethyl-

Botanical Aldehyde Semicarbazone

 spinosyn

 Bridged diphenyl Sodium nitrocompound

 Mixture of alkylbenzyl

 Carbamate Sterol

 dimethylammonium chlorides

 Carbamoyltriazole of different alkyl chain lengths Strobilurin

 Carbanilate Monoterpene 1, 4-Cineole Strobilurin Type- Methoxyacrylate

 Carbonitrile Morphactin

 Substituted benzene

Carboxamide Morpholine

 Sulfite ester

 Carboxylic acid Moulting hormone agonists

 sulfonamide

 Cationic surfactant Neonicotinoid

 sulfonanilide

Chlorinated acetal derivative of glucose Nereistoxin analogue Sulfonylurea

Chlorinated aromatic Nereistoxin analogue Sulphamide

sulphonamide hydrocarbon insecticides

 Chlorinated hydrocarbon Nitrile Surfactant

 Chlorinated phenol Nitroanisole Synthetic pyrethroid

 Chloroacetamide Nitrophenyl ether Tetracycline

 Chloroacetanilide Organoarsenic Tetramic Acid

 Chloroaniline Organochloride Tetrazine

 Chloronitrile Organochlorine Tetrazolinone

 Chlorophenoxy Acid Organochlorine, Racemic Tetronic Acid

 Chlorophenoxy acid ester gold mixture

 Thiadiazolylurea

 Chlorophenyl Organometal

 thiazole

 Conazole Organophosphate

 Thiazole carboximide

Racemic Organophosphate Coumarin

 thiazolidine

 mixture

 Thiocarbamate anticoagulant coumarin

 Organophosphorus

Cresol Thiocarbamide

 organothiophosphate

 Cyanoacetamide oxime Thiol

 organotin

Cyanoimidazole Thiol compound

 oxadiazine

Cyclic dithiocarbamate Thiophene

 oxadiazolone

Cyclodiene Thiourea

 Oxadiazolone / phenylurea

 Cyclodiene, organochlorine Triazine

 oxathiin

 Cyclohexadione Triazinone

 oxazole

 Cyclohexadione oxime Triazinylsulfonylurea

 oxazolidin

 Cyclohexanecarboxylate Triazole

derivative Oxidiazole

 Triazolepyrimidine

 Cyclohexanedione Oxime ether

 triazolinone

 Cyclohexanedione Oxirane oxime compound

 Triazolinthione

 Oxyacetamide Cyclooctane

 Triazolobenzothiazole

Cyclopropanecarboxamide, Petroleum derivative

 triazolone

isomer mixture Phenol

 triazolopyrimidine

 Cytokinin Phenoxipropionic acid

 triazolopyrimidine

 Diacylhydrazine Phenyl urea

 sulfonamide

 Dicarboximide Phenylamide

 Triazopyrimidine sulfonamide

Dicarboxylic acid Phenylfuranone

 Triketone

 Dimethyldithiocarbamate Phenylpyrazole

 uracil

 Dimethylurea Phenylpyridazine

 Uracil / amide

 Dinitroaniline Phenylpyridinamine

 Urea

 Dinitrophenol Phenylpyrrole

 Dinitrophenyl oxime Phenylurea

Diphenyl compound Pheromone As non-limiting examples of suitable active ingredients, the following products may be mentioned among others:

1, 2-benzisothiazolin-3-one amicarbazone

 1, 2-dibromoethane abamectin amidithion

 1, 2-dichloropropane acephate amidosulfuron

 1,3-dichloropropene acequinocyl aminocarb

 1-dodecanol acetamiprid aminopyralid

 1-methylcyclopropene acethion amisulbrom

 1-naphthylacetic acid acetic acid amitraz

 10,10'-acetochlor amitrole

oxybisphenoxarsine acibenzolar-S-methyl ammonium acetate

2- (thiocyanomethylthio) acifluorfen ammonium carbonate benzothiazole acifluorfen-sodium ammonium hydroxide

2,2-dibromo-3-aclonifen ammonium sulphamate nitrilopropionamide acrinathrin ammonium sulphate

2,3,6-TBA acrolein ammonium thiocyanate

2,4,5-trichlorophenol Adoxophyes orana ampropylfos

 2,4,5-trichlorophenoxy-granulovirus ancymidol

acetic acid alachlor anilazine

 2,4-D alanycarb anilofos

 2,4-DB albendazole anthracene oil

2,4-dimethylphenol aldicarb anthraquinone

 2,5-dichlorobenzoic acid aldimorph aramite

methyl ester aldoxycarb asomate

 2,6-diisopropylnaphthalene aldrin asulam sodium

 2-aminobutane allethrin asulam

 2-naphthyloxyacetic acid allidochlor atrazine

 2-phenylphenol alloxydim aviglycine-HCI

4-allylanisole alpha-chlorohydrin azaconazole

 4-aminopyridine alpha-cypermethrin azadirachtin

 4-CPA alpha-naphthylthiourea azafenidin

 5-methyl-2- (1-aluminum ammonium azamethiphos methylethyl) phenol sulphate azimsulfuron

 6-benzylaminopurine aluminum phosphide azinphos-ethyl

6-isopentenyl aminopurine aluminum sulphate azinphos-methyl

8-hydroxyquinoline sulfate ametryn aziprotryne azobenzene benzoylprop bromoxynil azocyclotin benzoylpropethyl bromuconazole azoxybenzene benzthiazuron bronopol azoxystrobin benzyl benzoate bufencarb

 beta-cyfluthrin buminafos

 Bacillus sphaericus beta-cypermethrin bupirimate

 Bacillus subtilis bifenazate buprofezin

 Bacillus thuringiensis bifenox butacarb barban bifenthrin butachlor barium polysulphide bilanafos butafenacil

Beauveria bassiana bilanafos-sodium butanethiol beflubutamid binapacryl butocarboxim benalaxyl bioallethrin butoxycarboximal benalaxyl-M bioresmethrin butralin

benazolin ethyl biphenyl butroxydim benazolin bispyribac-sodium buturon

bendiocarb bis-trichloromethyl sulfone butylate

benfluralin bistrifluron

benfuracarb bitertanol cadusafos benfuresate bixafen cafenstrole benodanil blasticidin-S calciferol benomyl bone oil calcium carbide benoxacor Bordeaux mixture calcium carbonate benquinox boscalid calcium chloride bensulfuron brodifacoum calcium hydroxide bensulfuron-methyl bromacil calcium phosphate bensulide bromadiolone calcium phosphide bensultap bromethalin camphechlor bentaluron bromobutide capsaicin bentazone bromocyclen captafol benthiavalicarb bromofenoxim captan

benzalkonium chloride bromomethane carbaryl benzfendizone bromophos carbendazim benzobicyclon bromophos-ethyl carbetamide benzofenap bromopropylate carbofuran benzoic acid bromoxynil heptanoate carbon dioxide benzoximate bromoxynil octanoate carbon tetrachloride carbophenothion chloroneb clopyralid

carbosulfan chlorophacinone cloquintocet-mexyl carboxin sulfoxide chlorophyllin cloransulam-methyl carboxin chloropicrin clothianidin carfentrazone-ethyl chloropropylate codlemone carpropamid chlorothalonil coniothyrium minitans cartap chlorotoluron copper (1) oxide chinomethionat chloroxuron copper II acetate chitosan chloroxylenol copper II carbonate chlomethoxyfen chlorphonium chloride copper II chloride chloralose chlorphoxim copper II hydroxide chloramben chlorpropham copper oxychloride chloranil chlorpyrifos copper sulphate chlorantraniliprole chlorpyrifos-methyl coumachlor chlorbenside chlorsulfuron coumafuryl chlorbromuron chlorthal-dimethyl coumaphos chlorbufam chlorthiamid coumatetralyl chlordane chlorthion crimidine

chlordecone chlorthiophos crotoxyphos chlordimeform chlozolinate crufomate

chloretazate cholecalciferol cufraneb

chlorethoxyfos choline chloride cuprobam

chlorfenac chromafenozide cyanamide chlorfenapyr cinnamon-ethyl cyanazine

chlorfenethol cinmethylin cyanofenphos chlorfenprop-methyl cinnamaldehyde cyanophos chlorfenson cinosulfuron cyazofamid chlorfensulphide citric anhydrous acid cyclanilide chlorfenvinphos citronella oil cycloate

chlorfluazuron clethodim cycloprothrin chlorflurenol clodinafop cyclosulfamuron chloridazon clodinafop-propargyl cycloxydim chlorimuron-ethyl cloethocarb cycluron

chlormephos clofencet Cydia pomonella chlormequat chloride clofentezine granulosis virus chlorobenzilate clomazone cyflufenamid chloromethiuron cloprop cyflumetofen cyfluthrin dichlofluanid dimefuron cyhalofop dichlone dimepiperate cyhalofop-butyl dichlormid dimethachlor cyhalothrin dichlorophen dimethametryn cyhexatin dichlorprop dimethenamid cymiazol dichlorprop-P dimethenamid-P cymoxanil dichlorvos dimethipin cypermethrin diclobutrazol dimethirimol cyphenothrin diclofop dimethoate cyproconazole diclofop-methyl dimethomorph cyprodinil diclomezine dimethrin cyprofuram dicloran dimethylvinphos cyprosulfamide diclosulam dimexano cyromazine dicofol dimoxystrobin dicrotophos diniconazole dalapon dicyclanil dinitramine dalapon-sodium dicyclopentadiene dinobuton daminozide didecyldimethylam dinocap dazomet chloride dinoseb

DDT dieldrin dinotefuran deltamethrin dienochlor dinoterb demeton diethofencarb dioxabenzophos demeton-O-methyl sulfone diethyltoluamide dioxacarb demeton-O-methyl difenacoum dioxathion demeton-S-methyl sulfone difenoconazole diphacinone demeton-S-methyl difenoxuron diphenamid denatonium benzoate difenzoquat diphenylamine desmedipham difethialone diquat dibromide desmetryn diflovidazin diquat

diflubenzuron disulfoton diflufenican diflubenzuron diflufenican diflufenzol diflufenzopyr dithinon diazinon diflumetorim dithlopyr dibromochloropropane difunon diuron

dicamba dikegulac DNOC

dichlobenil dikegulac-sodium dodecyl acetate dichlofenthion dimefox dodemorph acetate dodemorph etridiazole fentin acetate dodine etrimfos fentin chloride

 fentin hydroxide edifenphos famoxadone fentrazamide emamectin benzoate famphur fenuron

empenthrin farmesene fenvalerate endosulfan fatty acids ferbam

endothal fenamidone ferric phosphate endothion fenaminosulf fipronil

endrin fenamiphos flamprop

 EPN fenarimol flamprop-M-isopropyl epoxiconazole fenazaflor flazasulfuron eprinomectin fenazaquin flocoumafen

 EPTC fenbuconazole flonicamid

esfenvalerate fenbutatin oxide florasulam

esprocarb fenchlorazole fluacrypyrim etaconazole fenchlorazole-ethyl fluazifop-butyl ethaboxam fenchlorphos fluazifop-P-butyl ethalfluralin fenclorim fluazinam

ethametsulfuron-methyl fenfuram fluazolate

ethanedial fenhexamid fluazuron

ethanethiol fenitrothion flubendiamide ethephon Fenobucarb flubenzimine ethidimuron fenoprop flucarbazone-sodium ethiofencarb fenothiocarb flucetosulfuron ethion fenoxanil fluchloralin ethiprole fenoxaprop-ethyl flucycloxuron ethirimol fenoxaprop-P-ethyl flucythrinate ethoate-methyl fenoxycarb fludioxonil ethofumesate fenpiclonil flufenacet ethoprophos fenpropathrin flufenoxuron ethoxyquin fenpropidin flufenpyr-ethyl ethoxysulfuron fenpropimorph flumequine ethylene bisisothiocyanate fenpyroximate flumethrin

sulphide fenson flumetralin etofenprox fensulfothion flumetsulam etoxazole fenthion flumiclorac-pentyl flumioxazine fosamine hexaflumuron flumorph fosetyl hexazinone

fluometuron fosetyl-aluminum hexythiazox

fluopicolide fospirate hydramethylnon fluopyram fosthiazate hydrogen peroxide fluoroacetamide fosthietan hydroprene

fluorodifen fuberidazole hymexazol

fluoroglycofen furalaxyl

fluotrimazole furametpyr icaridin

fluoxastrobin furathiocarb imazalil

flupoxam furfural imazamethabenz flupropanate-sodium furilazole imazamethabenz-methyl flupyrsulfuron furmecyclox imazamox

flupyrsulfuron-methyl imazapic

fluquinconazole gamma-cyhalothrin imazapyr

flurazole gibberellic acid imazaquin

flurenol glufosinate imazethapyr

fluridone glufosinate-ammonium imazosulfuron flurochloridone glutaraldehyde imibenconazole fluroxypyr glyphosate trimesium imicyafos

fluroxypyr-meptyl glyphosate imidacloprid

flurprimidol gossyplure iminoctadine triacetate flurtamone guazatin iminoctadine

flusilazole imiprothrin

flusulfamide halfenprox indanofan

fluthiacet methyl halofenozide indolylacetic acid flutolanil halosulfuron-methyl indolylbutyric acid flutriafol haloxyfop indoxacarb

fluxofenim haloxyfop-etotyl iodofenphos

folpet haloxyfop-P iodomethane

fomesafen haloxyfop-P-methyl iodosulfuron

fonofos heptachlor iodosulfuron-methyl-foramsulfuron heptenophos sodium

forchlorfenuron hexachlorobenzene ioxynil octanoate formaldehyde hexachlorophene ioxynil

formetanate hexaconazole ipconazole

hexadecanoic acid formothion iprobenfos iprodione lenacil metaflumizone iprovalicarb leptophos metalaxyl

iron sulphate limonene metalaxyl-M isazofos lindane metaldehyde isobenzan linuron metamifop

isocarbophos lithium perfluorooctane metamitron isodrin sulfonate metam-sodium isofenphos-methyl lufenuron Metarhizium anisopliae isopolinate metazachlor isoprocarb magnesium phosphide metconazole isopropalin malathion methabenzthiazuron isoprothiolane maleic hydrazide methacrofos isoproturon mancopper methamidophos isopyrazam mancozeb methasulfocarb isotianil mandipropamid methazole

isoval maneb methfuroxam isoxaben MCPA methidathion isoxadifen ethyl MCPA-thioethyl methiocarb

isoxaflutole MCPB methomyl

isoxathion mecarbam methoprene ivermectin mecoprop methoprotryne

 mecoprop-P methoxychlor jasmone mefenacet methoxyfenozide

 mefenpyr methyl anthranilate kaolin mefluidide methyl nonyl ketone karbutilate menadione methylarsonic acid kasugamycin hydrochloride menazon metiram

hydrate mepanipyrim metobromuron kelevan mephosfolan metofluthrin kinetin mepiquat chloride metolachlor kinoprene mepiquat metominostrobin kresoxim-methyl mepronil metosulam

 meptyldinocap metoxuron

lactofen merphos metrafenone lambda-cyhalothrin mesosulfuron metribuzin

laminarin mesosulfuron-methyl metsulfovax

L-carvone mesotrione metsulfuron metsulfuron-methyl nuarimol paraffin oil (C18-C30) [1, mevinphos nuranone not ASU]

mexacarbate paraffin oil [3 Not NEU] milbemectin ocimene paraquat dichloride mirex octanal paraquat

octhilinone molinate parathion

monalide ofurace parathion-methyl monocrotophos olein pebulate

monolinuron omethoate pelargonic acid monosodium orbencarb penconazole

methylarsonate orthosulfamuron pencycuron

monuron orysastrobin pendimethalin

morphothion oryzalin penoxsulam

muscalure oxabetrinil pentachlorophenol myclobutanil oxadiargyl pentacosane

 oxadiazon pentanochlor

nabam oxadixyl penthiopyrad

naled oxamyl pentoxazone

naphthalene oxasulfuron permethrin

naproanilide oxaziclomefone peroxyacetic acid napropamide oxpoconazole fumarate pethoxamid

naptalam oxycarboxin phenkapton

neburon oxydemeton-methyl phenmedipham

nepetalactone oxyfluorfen phenothrin

nicosulfuron oxytetracycline phenthoate

Nicotine Phlebiopsis gigantea nitenpyram paclobutrazol phorate

nitralin Paecilomyces phosacetim

nitrapyrin fumosoroseus phosalone

nitrofen Paecilomyces lilacinus phosmet

nitrothal isopropyl paraffin oil (C1-C25) phosnichlor

 N-methylneodecanamide [4a] phosphamidon

norbormide paraffin oil (C1 1 -C30) phosphine

norflurazon [4c] phoxim

noruron paraffin oil (C15-C30) phthalide

novaluron [4b] picloram

noviflumuron paraffin oil (C17-C31) [2] picolinafen picoxystrobin propham pyriftalid

pinoxaden propiconazole pyrimethanil piperalin propineb pyriminobac-methyl piperidine propionic acid pyrimisulfan piperonyl butoxide propisochlor pyriprole piperophos propoxur pyriproxyfen pirimicarb propoxycarbazone pyrithiobac-sodium pirimiphos-ethyl propoxycarbazone-sodium pyroquilone pirimiphos-methyl propyzamide pyroxasulfone p-menthane-3,8-diol proquinazid pyroxsulam polynactins prosulfocarb

polyoxin prosulfuron quartz sand potassium bicarbonate prothiocarb quinalphos potassium iodide prothioconazole quinclorac potassium thiocyanate prothiofos quinmerac Prallethrin prothoate quinoclamine precocene II PT807-HCl quinoxyfen pretilachlor putrescine quintozene primisulfuron methyl pymetrozine quizalofop-ethyl primisulfuron pyraclofos quizalofop-P-ethyl prochloraz pyraclonil quizalofop-P-tefuryl procymidone pyraclostrobin

prodiamine pyraflufen resmethrin profenofos pyraflufen-ethyl rimsulfuron profoxydim pyrasulfotol rotenone prohexadione calcium pyrazophos

promecarb pyrazosulfuron-ethyl sabadilla prometon pyrazoxyfen saflufenacil prometryn pyrethrins scilliroside propachlor pyribenzoxim sebuthylazine propamocarb hydrochloride pyridaben secbumeton propamocarb pyridafenthion sethoxydim propanil pyridafol siduron

propaquizafop pyridalyl silica

propargite pyridate silthiofam propazine pyrifenox simazine propetamphos pyrifluquinazon simeconazole simetryn tebupirimfos: hiofanox

sintofen tebutam: hiometon

 S-methoprene tebuthiuron: hionazin

 S-metolachlor tecloftalam: hiophanate-methyl sodium 5-nitroguaiacolate tecnazene: hiosultap

sodium carbonate teflubenzuron: hiosultapodium-disodium sodium chlorate tefluthrin: hiosultap-monosodium sodium chloride tembotrione: hiourea

sodium hypochlorite temephos: hiram

sodium o-nitrophenolate tepraloxydim: iocarbazil

p-nitrophenolate terbacil sodium: olclofos-methyl spinetoram terbufos: olylfluanid

spinosad terbumeton: opramezone spirodiclofen terbuthylazine ralkoxydim

spiromesifen terbutryn ralomethrin spirotetramat tetrachlorvinphos ransfluthrin spiroxamine tetraconazole riadimefon streptomycin tetradifon riadimenol strobane tetraethyl pyrophosphate: ri-allate

sucrose octanoate tetramethrin riapenthenol sulcotrione tetrasul riasulfuron sulfentrazone thenylchlor Tiazamate

sulfluramid thiabendazole riazophos

sulfometuron-methyl thiacloprid riazoxide

sulfosulfuron thiamethoxam ribenuron

sulfotep thiazafluron ribenuron-methyl sulfuryl fluoride thiazopyr ribufos

sulphur thidiazuron richlorfon

sulphuric acid thiencarbazone-methyl richloronate sulprofos thifensulfuron riclopyr

 thifensulfuron-methyl ricosane

tau-fluvalinate thifluzamide ricyclazole

 TCA-sodium thiobencarb ridemorph

 TDE thiocyclam hydrogen ridiphane

tebuconazole oxalate rietazine

tebufenozide thiocyclam rifloxystrobin tebufenpyrad thiodicarb rifloxysulfuron trifloxysulfuron-sodium triflumizole triflumuron trifluralin

triflusulfuron triflusulfuron-methyl triforine

TML

trimethacarb trinexapac-ethyl triticonazole tritosulfuron uniconazole urea sulphate validamycin vamidothion vernolate

verticillium lecanii vinclozolin warfarin

XMC zeatin

zeta-cypermethrin zinc oxide zineb

ziram

zoxamide The non-water-soluble products are preferably chosen from this list. These products and denominations are known to those skilled in the art. Several active plant protection products can be combined.

Surfactant (c) optional

 The phytosanitary formulation may comprise at least one surfactant. It may comprise a mixture of several different surfactants. The surfactant may facilitate emulsification or dispersion after placing the formulation in the presence of water, and / or stabilize (in time and / or temperature) the formulation or the dispersion, for example by avoiding a sedimentation.

 Surfactants are known compounds, which have a generally relatively low molar mass, for example less than 1000 g / mol. The surfactant can be an anionic surfactant in salified or acidic form, preferably polyalkoxylated nonionic, cationic, amphoteric (term also including zwitterionic surfactants). It may be a mixture or combination of these surfactants.

 As examples of anionic surfactants, mention may be made, without intending to be limited thereto:

alkylsulphonic acids, arylsulphonic acids, optionally substituted with one or more hydrocarbon groups, and whose acidic function is partially or totally salified, such as C ₈ -C ₅ o alkylsulphonic acids, more particularly C ₈ -C ₃ o preferably C ₁ -C ₂₂ , benzenesulphonic acids, naphthalenesulphonic acids, substituted with one to three C 1 -C ₃₀ alkyl groups, preferably C ₄ -C ₆ alkyl groups, and / or C ₂ -C ₃ alkenyl groups; o, preferably C ₄ -C ₆ .

the mono- or diesters of alkylsulfosuccinic acids, of which the linear or branched alkyl part, optionally substituted with one or more hydroxylated and / or alkoxylated, linear or branched C ₂ -C ₄ (preferably ethoxylated, propoxylated, ethopropoxylated) groups; ).

the phosphate esters chosen more particularly from those comprising at least one saturated, unsaturated or aromatic hydrocarbon group, linear or branched, comprising 8 to 40 carbon atoms, preferably 10 to 30, optionally substituted by at least one alkoxylated (ethoxylated) group, propoxylated, ethopropoxylated). In addition, they comprise at least one phosphate ester group, mono- or diesterified, so that one or two free or partially or totally salified acid groups. The preferred phosphate esters are of the mono- and diester type of phosphoric acid and of alkoxylated (ethoxylated and / or propoxylated) mono-, di- or tristyrylphenol, or of alkoxylated (ethoxylated) mono-, di- or trialkylphenol and / or propoxylated), optionally substituted with one to four alkyl groups; phosphoric acid and an alcohol C ₈ -C ₃ o, preferably C ₁₀ -C ₂₂ alkoxylated (ethoxylated or ethopropoxylated); phosphoric acid and a C ₈ -C ₂₂ alcohol, preferably C ₁₀ -C ₂₂ , non-alkoxylated.

sulphate esters obtained from saturated or aromatic alcohols, optionally substituted with one or more alkoxylated groups (ethoxylated, propoxylated, ethopropoxylated), and for which the sulphate functional groups are in the free acid form, or partially or completely neutralized . By way of example, mention may be made of sulfate esters obtained more particularly from saturated or unsaturated C ₈ -C ₂₀ alcohols, which may comprise 1 to 8 alkoxylated units (ethoxylated, propoxylated, ethopropoxylated); sulphate esters obtained from polyalkoxylated phenol, substituted with 1 to 3 saturated or unsaturated C ₂ -C ₃₀ hydroxycarbon groups, and in which the number of alkoxylated units is between 2 and 40; sulfate esters obtained from polyalkoxylated mono-, di- or tristyrylphenol in which the number of alkoxylated units ranges from 2 to 40.

The anionic surfactants may be in acid form (they are potentially anionic), or in partially or totally salified form, with a counterion. The counterion may be an alkali metal, such as sodium or potassium, an alkaline earth metal, such as calcium, or an ammonium ion of formula N (R) ₄ ⁺ in which R, identical or different, represent a hydrogen atom or an alkyl radical in dC ₄ optionally substituted with an oxygen atom.

 As examples of nonionic surfactants, mention may be made, without intention of being limited thereto:

- polyalkoxylated (ethoxylated, propoxylated, ethopropoxylated) substituted by at least one alkyl radical C ₄ -C _20, preferably C ₄ -C _2, or substituted by at least one alkylaryl radical in which the alkyl part is CC ₆ . More particularly, the total number of alkoxylated units is between 2 and 100. By way of example, mention may be made of polyalkoxylated mono-, di- or tri (phenylethyl) phenols, or polyalkoxylated nonylphenols. Among the ethoxylated and / or propoxylated, sulphated and / or phosphated di- or tristyrylphenols, mention may be made of ethoxylated di- (1-phenylethyl) phenol, containing 10 oxyethylenated units, di-phenyl-1 Ethyl ethoxylated phenol, containing 7 oxyethylenated units, sulfated ethoxylated di- (1-phenylethyl) phenol, containing 7 oxyethylenated units, ethoxylated tri- (1-phenylethyl) phenol, containing 8 oxyethylenated units, tri-phenyl Ethoxylated ethyl ether, containing 16 oxyethylene units, sulfated ethoxylated tri- (1-phenylethyl) phenol, containing 16 oxyethylene units, ethoxylated tri- (1-phenylethyl) phenol containing 20 oxyethylenated units, Phosphated ethoxylated phenyl-1-ethylphenol, containing 16 oxyethylenated units.

alcohols or fatty acids C ₆ -C _{22 which are} polyalkoxylated (ethoxylated, propoxylated, ethopropoxylated). The number of alkoxylated units is between 1 and 60. The term ethoxylated fatty acid includes both the products obtained by ethoxylation of a fatty acid with ethylene oxide and those obtained by esterification of a fatty acid with a polyethylene glycol. .

 polyalkoxylated triglycerides (ethoxylated, propoxylated, ethopropoxylated) of vegetable or animal origin. Thus triglycerides from lard, tallow, peanut oil, butter oil, cottonseed oil, linseed oil, olive oil, are suitable. palm oil, grape seed oil, fish oil, soybean oil, castor oil, rapeseed oil, coconut oil coconut oil, and comprising a total number of alkoxylated units of between 1 and 60. The term ethoxylated triglyceride is intended both for the products obtained by ethoxylation of a triglyceride by ethylene oxide and those obtained by ethoxylation of a triglyceride with ethylene oxide. by trans-esterification of a triglyceride with a polyethylene glycol.

- sorbitan esters, optionally polyalkoxylated (ethoxylated, propoxylated, ethopropoxylated), particularly cyclized sorbitol esters of fatty acids of C10 to C ₂ o as lauric acid, stearic acid or oleic acid, and comprising a total number of alkoxylated units of between 2 and 50.

Useful emulsifiers include the following products, all marketed by Rhodia:

 - Soprophor® TSP / 724: surfactant based on ethopropoxylated tristyrylphonol

- Soprophor® 796/0: surfactant based on ethopropoxylated tristyrylphonol

- Soprophor® CY 8: surfactant based on ethoxylated tristyrylphonol

 - Soprophor® BSU: surfactant based on ethoxylated tristyrylphonol

 - Alkamuls® RC: surfactant based on ethoxylated castor oil

 - Alkamuls® OR / 36: surfactant based on ethoxylated castor oil

- Alkamuls® T / 20: surfactant based on a sorbitan ester Geronol® TBE-724: surfactant mixture comprising ethopropoxylated nonionic surfactant.

When it contains, the formulation of the invention advantageously comprises at least 4%, preferably at least 6%, preferably at least 10%, and preferably at least 15% by weight of dry matter, at least a surfactant c).

Other details regarding the phytosanitary formulation

 The phytosanitary formulation, concentrated, preferably does not include significant amounts of water. Typically the water content is less than 50% by weight, preferably less than 25% by weight. It may be generally less than 10% by weight.

 The formulation is preferably a liquid formulation, for example in the form of an emulsifiable concentrate (EC), a liquid concentrate (SL), a concentrated emulsion (EW), a suspoemulsion (SE), or a micoremulsion (ME).

In this case, it preferably comprises less than 500 g / l of water, more preferably less than 250 g / l. It will generally be less than 100 g / L.

The formulations may advantageously comprise:

 a) from 5 to 70%, preferably from 10 to 50%, of the phytosanitary product, by weight of active ingredient,

 b) from 10 to 95%, preferably from 20 to 80%, of the solvent, by weight,

 c) from 0 to 60%, preferably from 5 to 50%, preferably from 8 to 25%, by weight of dry matter, of surfactant,

 d) from 0 to 10% by weight of water.

It is not excluded to produce solid formulations, for example formulations in which a liquid comprising the phytosanitary product solubilized in the solvent, is supported by a mineral and / or dispersed in a solid matrix.

The formulation may of course comprise other ingredients (or "other additives") than the active plant protection product, compound of formula (I), the optional surfactant (s) and the optional water. It may in particular comprise co-solvents, dispersing agents, viscosity modifying agents, control agents for rheology, fertilizers, anti-foaming agents, in particular silicone antifoams, anti-rebound agents, antilessivage agents, inert fillers, in particular mineral fillers, anti-freeze agents, crystallization inhibitors such as fatty acids or non-polyalkoxylated fatty alcohols, for example the product Alkamuls® OL700 sold by Rhodia, mixtures or combinations.

Co-solvent

 According to a particular embodiment, the compound of the invention is used in the phytosanitary formulation as a co-solvent, in combination with another solvent or a mixture of other solvents. The other co-solvent (s) may be subsequently designated as co-solvent (s). The weight ratio between the compound of the invention and the other solvent may especially be between 10/90 and 90/10, for example between 10/50 and 50/50 or between 50/50 and 90/10.

As examples of other solvents that can be used, mention is made in particular of:

 aliphatic solvents,

 - branched or linear chain paraffins

 cyclic hydrocarbons

 - aromatic solvents

 - phosphorus solvents

 - sulfur solvents

 - the nitrogenous solvents

 aliphatic mono-, di- or triesters

 cyclic esters

 cyclic, aliphatic and / or aromatic ketones

 - alkylcyclohexanones

 - dialkylketones

 - acetoacetates

 benzylketones

 - acetophenone

 - alcohols

 - cycloalcohols

 glycols, glycol ethers, and their polymers

- propylene glycols - glycol ether acetates

 - aromatic alcohols

 - carbonates

 - the ethers

 halogenated solvents.

We particularly prefer:

 alkylated benzenes and naphthalenes,

 - Solvesso® 100, 150, 200 products in their standard and ND versions

alkanolamides and their alkyl ethers,

 fatty acids and their alkyl esters, especially methyl esters, for example methyl oleate,

 alkyldimethylamides

 N-alkyl-pyrrolidones, in particular N-methyl-pyrrolidone and N-ethyl-pyrrolidone

 - trialkylphosphates

 linear or branched aliphatic alcohols and their esters

 dicarboxylic acid diesters

 - linear or branched paraffins

 - white oils

 - glycols and glycol ethers

 - acetophenone

 - butyrolactone

 - DMSO.

Preparation and use of the formulation

 Conventional methods for preparing phytosanitary formulations or solvent mixtures can be implemented. It can be operated by simple mixing of the constituents.

The concentrated phytosanitary formulation is intended to be spread over a cultivated field or to be cultivated, for example a soybean field, most often after dilution in water, to obtain a diluted composition. The dilution is generally carried out by the farmer, directly in a tank ("tank-mix"), for example in the tank of a device for spreading the composition. It is not excluded that the operator adds other plant protection products, for example fungicides, herbicides, pesticides, insecticides, fertilizers. Thus, the formulation can be used to prepare a composition diluted in the water of the active plant protection product, by mixing at least one part by weight of concentrated formulation with at least 10 parts of water, preferably less than 1000 parts. Dilution rates and amounts to be applied in the field usually depend on the crop product and the desired dose to treat the field; this can be determined by the farmer.

Other details or advantages may appear in light of the examples which follow, without being limiting in nature.

EXAMPLES

Example 1.1 Preparation of a Hydroxydimethylamide of Formula HO

The synthetic route is as follows: n = 3 to 5

The typical procedure for n ranging from 3 to 5 is as follows.

In a 500 ml flask containing the lactone (1 mole) is cast in about 1 hour and at + 25% dimethylamine in aqueous solution (60% by weight) (1.5 moles). The mixture is stirred at this temperature until complete consumption of the lactone (about 3 to 4 hours). The crude reaction product is then neutralized by addition of a 37% by weight aqueous hydrochloric acid solution until a pH of 7 is obtained. The aqueous phase is then extracted (3 ^* 100 ml) with an immiscible organic solvent in the aqueous solution. water (dichloromethane or ethyl acetate). The organic phases are combined, dried over sodium sulfate and the solvent is evaporated under partial vacuum. The residue is engaged as such in the next step of functionalization. Example 1.2 Preparation of a Methoxyalkyldimethylamide of Formula

The synthetic route is as follows:

The procedure for n = 3 is as follows.

 In a 2000 ml flask containing hydroxyamide (compound A3) (435 g, 3.28 moles) and THF (960 g) was added powdered sodium hydroxide (170 g, 4.22 moles) at +25 ° C. . On this mixture, dimethylsulfate (508 g, 3.99 moles) is cast in 1.5 hours while maintaining the temperature of the reaction medium below + 45 ° C. The mixture is kept at + 50 ° under stirring until complete consumption of the starting hydroxyamide (approximately 20 hours). The reaction crude is then diluted with water (1633 g) and dichloromethane (1325 g). The organic phase is separated from the aqueous phase. The latter is extracted twice with about 1300 g of dichloromethane. The organic phases are combined, dried over sodium sulfate and the solvent is evaporated under partial vacuum. The desired product (425 g) is then obtained with a purity higher than 98% (yield: 89%).

The procedure for n = 4 is as follows.

In a 1000 ml flask containing hydroxyamide (compound A4) (246 g; 1.7 mole) and THF (500 g) is added sodium hydroxide (87.2 g, 2.18 mole) to +25 ° C. On this mixture, dimethylsulfate (265 g, 2.07 moles) is cast in 1.5 hours while maintaining the temperature of the reaction medium below + 45 ° C. The mixture is kept at + 50 ° under stirring until complete consumption of the starting hydroxyamide (approximately 20 hours). The reaction crude is then diluted with water (1200 g) and dichloromethane (1200 g). The organic phase is separated from the aqueous phase. The latter is extracted twice with about 1200 g of dichloromethane. The organic phases are combined, dried over sodium sulfate and the solvent is evaporated under partial vacuum. The desired product (216 g) is then obtained with a purity of the order of 98% (yield: 80%). The procedure for n = 5 is as follows.

 In a 2000 ml flask containing hydroxyamide (Compounds A5) (334 g, 2.1 moles) and THF (600 g) is added sodium hydroxide (108 g, 2.7 moles) at +25 ° C. . On this mixture, dimethylsulfate (327 g, 2.56 moles) is cast in 1.5 hours while maintaining the temperature of the reaction medium below + 45 ° C. The mixture is kept at + 50 ° under stirring until complete consumption of the starting hydroxyamide (approximately 20 hours). The reaction crude is then diluted with water (1300 g) and dichloromethane (1300 g). The organic phase is separated from the aqueous phase. The latter is extracted twice with about 1200 g of dichloromethane. The organic phases are combined, dried over sodium sulfate and the solvent is evaporated under partial vacuum. The desired product (330 g) is then obtained with a purity higher than 98% (yield: 91%).

The table below summarizes the various products synthesized, the yields and their purities.

Example 1.3 - Preparation of éthoxyalkyldiméthylamide of formula _CH? -

The synthetic route is as follows:

The procedure for n = 3 is as follows.

In a 250 mL flask containing deoiled sodium hydride (1.45 g, 60.5 mmol) in THF (130 g) maintained at 0 ° C, the above hydroxyamide A3 (5.89 g, 45.0 mmol) is added over 30 minutes. To this mixture, the iodoethane (10.4 g, 66.4 mmol) is added in 30 minutes and at Ο 'Ό. The mixture is maintained at +25 ° C. with stirring until the complete consumption of the starting hydroxyamide (approximately 20 hours). The reaction crude is then diluted with water (50 g) and dichloromethane (150 g). The organic phase is washed successively with a saturated solution of ammonium chloride (50 ml), sodium hydrogen carbonate (50 ml) and water (50 ml). The organic phase is dried over sodium sulphate and the solvent is evaporated under partial vacuum. The desired product (4.0 g) is then obtained with a purity of the order of 97.5% (yield: 56%).

The procedure for n = 4 is as follows.

 In a 250 mL flask containing deoiled sodium hydride (1.14 g, 47.5 mmol) in THF (172 g) maintained at Ο 'Ό, the previous hydroxyamide A4 (5.23 g; 3 mmol) is added in 30 minutes. To this mixture, the iodoethane (7.46 g, 52.1 mmol) is added in 30 minutes and at Ο 'Ό. The mixture is maintained at +25 ° C. with stirring until the complete consumption of the starting hydroxyamide (approximately 20 hours). The reaction crude is then diluted with water (50 g) and dichloromethane (150 g). The organic phase is washed successively with a saturated solution of ammonium chloride (50 ml), sodium hydrogen carbonate (50 ml) and water (50 ml). The organic phase is dried over sodium sulphate and the solvent is evaporated under partial vacuum. The desired product (2.8 g) is then obtained with a purity higher than 98% (yield: 48%).

The procedure for n = 5 is as follows.

In a 250 mL flask containing deoiled sodium hydride (1.03 g, 43.2 mmol) in THF (150 g) maintained at Ο 'Ό, the previous hydroxyamide A5 (5.1 g; 1 mmol) is added in 30 minutes. To this mixture, iodoethane (7.4 g, 47.4 mmol) is added over 30 minutes and at 0 ° C. The mixture is maintained at +25 ° C. with stirring until the complete consumption of the starting hydroxyamide (approximately 20 hours). The reaction crude is then diluted with water (50 g) and dichloromethane (150 g). The organic phase is washed successively with a saturated solution of ammonium chloride (50 ml), sodium hydrogen carbonate (50 ml) and water (50 ml). The organic phase is dried over sodium sulphate and the solvent is evaporated under partial vacuum. The desired product (1.9 g) is then obtained with a purity higher than 98% (yield: 32%). The table below summarizes the various products synthesized, the yields and their purities.

The same modes of synthesis were carried out for the preparation of the branched derivatives by using as raw material the corresponding lactones.

Example 2 - Phytosanitary Formulations

 By mixing the ingredients, formulations of various phytosanitary actives of emulsifiable concentrate type (EC) are prepared.

 The formulations include:

 the active ingredient, in quantity by weight (of active ingredient) indicated in the table below,

 - 10% by weight of Alkamuls® RC surfactant, marketed by Rhodia

and, as a solvent, the remainder of the compounds of the examples. Examples 2 are comparative examples in which the product Rhodiasolv® ADMA10, or Rhodiasolv® ADMA810, Rhodia (Asia Pacific zone) is used as solvent: Alkydimethylamide solvents.

The following tests are carried out:

 - Visual observation at 25 ° C - We note the appearance of the formulation and we possibly identify the presence of crystals

 - Visual observation at Ο 'Ό - We place the formulation for 7 days at 0 ° C and note the appearance of the formulation and possibly identify the presence of crystals (CIPAC MT39 test)

 - Visual observation at 0 ° C with nucleation: A crystal of the active ingredient is introduced into the formulation which has spent 7 days at Ο'Ό for nucleation, and the formulation is again placed for 7 days at 0 ° C. The appearance of the formulation is noted and the presence of crystals is optionally identified.

Appearance Appearance at 0 ° C

Active Solvent

 at 25 ° C with nucleation

Rhodiasolv®

 Chlorpyrifos 40% Limpide Limpide Limpide ADMA 10

 Rhodiasolv®

 a-Cypermethrin 1 0% Limpide Limpide Limpide ADMA 10

 Rhodiasolv®

 Phenmedipham 16% Limpide Limpide Limpide ADMA 10

 Rhodiasolv®

 Propanil 36% Limpide Limpide Limpide ADMA 10

 Rhodiasolv®

 Tebuconazole 25% Limpide Limpide Limpide ADMA 10

 Rhodiasolv®

 Trifluralin 40% Limpide Limpide Crystals ADMA 10

 Rhodiasolv®

 Difenconazole 25% Limpide Limpide Crystals ADMA 10

 Rhodiasolv®

 Dimethoate 40% Trouble Trouble Crystals ADMA 10

 Rhodiasolv®

 Oxyfluorfen 22% Limpide Limpide Crystals ADMA 10

 Rhodiasolv®

 Propoxur 20% Clear Limpide Crystals ADMA 10

 Rhodiasolv®

 Chlorpyrifos 40% Limpide Limpide Limpide ADMA 810

 Rhodiasolv®

 a-Cypermethrin 1 0% Limpide Limpide Limpide ADMA 810

 Rhodiasolv®

Phenmedipham 16% Limpide Limpide Limpide ADMA 810 Rhodiasolv®

 Propanil 36% Limpide Limpide Limpide ADMA 810

 Rhodiasolv®

 Tebuconazole 25% Limpide Limpide Limpide ADMA 810

 Rhodiasolv®

 Azoxystrobin 25% Not soluble Not soluble Not soluble ADMA 810

 Compound 1 Chlorpyrifos 40% Limpid Clear Limpid

Compound 1 a-Cypermethrin 1 0% Limpid Clear Limpid

Compound 1 Phenmedipham 16% Clear Limpide Clear

Compound 1 Propanil 36% Clear Limpide Clear

Compound 1 Tebuconazole 25% Limpide Limpide Limpide

Compound 1 Trifluralin 40% Limpid Limpide Limpid

Compound 1 Difenconazole 25% Limpide Limpide Limpide

Compound 1 Dimethoate 40% Limpide Limpide Limpide

Compound 1 Oxyfluorfen 22% Limpid Limpide Limpid

Compound 1 Propoxur 20% Limpid Limpide Limpid

Compound 1 Azoxystrobin 25% Limpid Limpide Crystals

Compound 4 Phenmedipham 16% Limpid Clear Limpid

Compound 4 Propanil 36% Clear Limpide Clear

Compound 4 Tebuconazole 25% Limpid Limpide Limpide

Compound 4 Trifluralin 40% Clear Limpide Crystals

Compound 4 Difenconazole 25% Limpide Limpide Limpide

Compound 4 Dimethoate 40% Limpide Limpide Limpide

Compound 4 Oxyfluorfen 22% Trouble Trouble Trouble

Compound 4 Propoxur 20% Clear Limpide Clear

Compound 4 Azoxystrobin 25% Crystals Crystal Crystals

Claims

1. Phytosanitary formulation comprising at least:

 (a) an active plant protection product,

 b) a compound of formula (I) below:

R ^a R ^b C (OR) -AC (O) -NR ² R ³ (I)

 in which :

- R ^a and R ^b , identical or different, are groups selected from hydrogen atom and linear or branched alkyl groups, especially CC ₆ ;

- R ¹ is a hydrocarbon group comprising an average number of carbon atoms ranging from 1 to 36, saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic, optionally substituted;

R ² and R ³ , which are identical or different, are groups chosen from a hydrogen atom and hydrocarbon groups comprising an average number of carbon atoms ranging from 1 to 36, saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic, optionally substituted, R ² and R ³ may optionally form together a ring comprising the nitrogen atom to which they are bonded, optionally substituted and / or optionally comprising an additional heteroatom,

 - A represents a linear or branched alkyl group, the main chain comprises at least 2 carbon atoms;

 c) optionally a surfactant, and

 d) possibly water.

2. Formulation according to claim 1, comprising a compound of formula (I) in which R ^a and R ^b , which are identical or different, are groups chosen from a hydrogen atom and linear or branched alkyl groups with CC ₃ .

3. Formulation according to any one of the preceding claims, comprising a compound of formula (I) wherein at least one of the groups selected from R ^a and R ^b is a group selected from linear or branched alkyl groups of CC ₆ , preferably CC ₃ , especially a methyl or ethyl group.

4. Formulation according to any one of the preceding claims, comprising a compound of formula (I) in which A represents a linear or branched alkyl group whose main chain comprises from 2 to 8 carbon atoms, for example from 2 to 6 carbon atoms, preferably from 2 to 4 carbon atoms.

5. Formulation according to any one of the preceding claims, comprising a compound of formula (I) in which R ² and R ³ , which are identical or different, are chosen from methyl, ethyl, propyl (n-propyl) and isopropyl groups. , n-butyl, isobutyl, n-pentyl, amyl, isoamyl, hexyl, cyclohexyl, mixtures thereof and / or combinations thereof. R ² and R ³ may also be such that together they form with the nitrogen atom a morpholine, pyrrolidine, piperazine or piperidine group.

A formulation according to any one of the preceding claims, comprising a compound of formula (I) wherein R ¹ is a hydrocarbon group selected from methyl, ethyl, propyl (n-propyl), isopropyl, n-butyl, isobutyl , n-pentyl, amyl, isoamyl, hexyl, or cyclohexyl.

A formulation according to any one of the preceding claims, comprising a compound of formula (I) selected from one of the following compounds:

CH ₃ 0-CH ₂ -CH ₂ -CH ₂ -CONMe ₂

CH ₃ 0-CH ₂ -CH ₂ -CH ₂ -CH ₂ -CONMe ₂

CH ₃ 0-CH ₂ -CH ₂ -CH ₂ -CH ₂ -CH ₂ -CONMe ₂

C ₂ H ₅ 0-CH ₂ -CH ₂ -CH ₂ -CONMe ₂

C ₂ H ₅ 0-CH ₂ -CH ₂ -CH ₂ -CH ₂ -CONMe ₂

C ₂ H ₅ 0-CH ₂ -CH ₂ -CH ₂ -CH ₂ -CH ₂ -CONMe ₂

8. Formulation according to any one of the preceding claims, characterized in that it comprises a surfactant c), selected from anionic surfactants in salified or acidic form, nonionic, preferably nonionic polyalkoxylated, cationic, or amphoteric.

9. Formulation according to any one of the preceding claims, characterized in that it is in the form of an emulsifiable concentrate (EC), a liquid concentrate (SL), a concentrated emulsion (EW), a suspoemulsion (SE), or a micoremulsion (ME).

10. Use of a compound of formula (I) as defined in any one of claims 1 to 9 in phytosanitary formulations comprising a) an active plant protection product, c) optionally a surfactant, and d) optionally the water, as a solvent, co-solvent, crystallization inhibitor, and / or agent for increasing the bioactivity of said active plant protection product.