WO2010109301A1

WO2010109301A1 - Benzamidic compounds having fungicidal activity and relative use

Info

Publication number: WO2010109301A1
Application number: PCT/IB2010/000650
Authority: WO
Inventors: Isabella Venturini; Lucio Filippini; Matteo Santino Vazzola
Original assignee: Isagro Ricerca S.R.L.
Priority date: 2009-03-27
Filing date: 2010-03-19
Publication date: 2010-09-30
Also published as: ITMI20090488A1

Abstract

The present invention relates to benzamidic compounds having general formula (I): wherein: R_x represents a halogen atom or a methyl group possibly substituted by fluorine atoms; R₁, R₂, R₃, independently from each other, represent a C₁- C₃ alkyl group; R₄ represents a hydrogen atom or a C₁-C₃ alkyl group; R_y represents a halogen atom, a C₁-C₄ alkyl group, a C₁-C₄ haloalkyl group, a C₁-C₄ alcoxy group, a C₁-C₄ haloalcoxy group; n represents an integer ranging of from 0 to 3. The present invention also relates to the use of the above benzamidic compounds for the control of fungi, bacteria and phytopathogenic viruses of agricultural crops.

Description

BENZAMIDIC COMPOUNDS HAVING FUNGICIDAL ACTIVITY AND RELATIVE USE

The present invention relates to new benzamidic compounds and their use for the control of phytopathogenic fungi .

More specifically, it relates to new indanyl benzamides having a high activity in the control of pathogenic fungi of important agricultural crops .

European patent application EP0086111 describes benzamides deriving from benzoic acids monosubstituted in ortho position, condensed with 4-aminoindanyls optionally substituted in positions 1, 2 and 3 by C_x-C₃ alkyl groups; N- (1, 1, 3 -trimethyl-4-indanyl) -2-trifluoromethyl- benzamide, which corresponds to compound Nr. 17 of EP0086111 and to compound Nr. 1 of Japanese patent application Nr. JP59144744, is indicated as being among the preferred examples of this series. Japanese patent application Nr. JP61280460 also describes benzamides deriving from di- or tri-substituted benzoic acids, containing the group 1, 1-dimethyl-4 -indanyl in the amine part; among the preferred compounds, Nr. 1 corresponds to N- (1, 1-dimethyl-4 -indanyl) -2-fluoro-6-trifluoromethyl- benzamide .

The indanyl benzamides described in the state of the art, however, are not completely satisfactory from the point of view of the level of fungicidal activity against phytopathogenic fungi, the range of action, and the phytotoxicity with respect to the agricultural crops to be protected.

The Applicant has now surprisingly found that the benzamidic compounds obtained by the reaction of benzoic acids di-substituted with a fluorine atom and with specific groupings, with aniline containing the indanyl group tri-substituted in positions 1,1,3 by C₁-C₃ alkyl groups, overcome the drawbacks of the benzamidic compounds according to the known art, revealing an improved fungicidal activity, a wider range of action and a reduced or zero phytotoxicity with respect to the most important agricultural crops .

A first object of the present invention therefore relates to benzamidic compounds having general formula (I)

(I)

wherein:

R_x represents a halogen atom or a methyl group optionally substituted by fluorine atoms;

Ri, R₂, R₃, independently from each other, represent a C₁-

C₃ alkyl group,- R₄ represents a hydrogen atom or a C₁-C₃ alkyl group; Ry represents a halogen atom, a Ci-C₄ alkyl group, a Ci-C₄ haloalkyl group, a Ci-C₄ alcoxy group, a Ci-C₄ haloalcoxy group; n represents an integer ranging from 0 to 3.

Preferred benzamidic compounds having general formula (I) are compounds in which the fluorine atom F is in ortho position with respect to the benzamidic group,

R_x is a trifluoromethyl, R₁, R₂ e R₃ represent a methyl and R₄ is a hydrogen atom.

Examples of compounds having general formula (I) , which are preferred as they have a particularly high fungicidal activity, are the following:

1) N- (1, 1, 3-trimethyl-4-indanyl) -2-fluoro-6-trifluoro- methylbenzamide;

2) N- (1, 1, 3-trimethyl-4-indanyl) -4-fluoro-6-trifluoro- methylbenzamide ;

3) N- (1, 1, 3-trimethyl-4-indanyl) -2-fluoro-6-methylbenzamide ; 4) N- (1, 1, 3-trimethyl-4-indanyl) -3-fluoro-2-methyl- benzamide;

5) N- (1, 1, 3-trimethyl-4-indanyl) -2-fluoro-6-difluoro- methylbenzamide ;

6) N- (1, 1, 3-trimethyl-4-indanyl) -4-fluoro-6-difluoro- methylbenzamide;

7) N- (1, 1, 3-trimethyl-4-indanyl) -2, 6-difluorobenz- amide ; 8) N- (1, 1, 3-trimethyl-4-indanyl) -2-fluoro-6-iodo- benzamide ;

9) N- (1, 1, 3-trimethyl-4-indanyl) -2-chloro-6-fluoro- benzamide ; The compound N- (1, 1, 3-trimethyl-4-indanyl) -2-fluoro- 6-trifluoro-methylbenzamide is particularly preferred.

Compounds having general formula (I) which are particularly preferred are those in which the fluorine atom F is in ortho position with respect to the benzamidic group.

Compounds in which R_x is a trifluoromethyl are particularly preferred.

Compounds in which R₁, R₂ and R₃ represent methyl are also preferred. Compounds in which R₄ represent a hydrogen atom are also preferred.

Due to the asymmetry of the carbon atom in position

3 of the indanyl ring, and possibly of the atoms in position 1 (when R_x is different from R₂) and 2 (when R₄ represents an alkyl group) , the compounds having formula

(I) can be in the form of mixtures of optical isomers and possibly diastereoisomers .

The compounds having general formula (I) therefore fall within the range of the present invention both as racemic and possibly diastereoisomeric mixtures, and as partially separate mixtures, and also as single optical isomers and possible single diastereoisomers. The compounds having general formula (I) are prepared by reacting a substituted benzoic acid or one of its derivatives having formula (II) , with an aniline having formula (III) , according to the following reaction scheme :

(D

In formulae (I) , (II) and (III) :

Ri_/ R_2/ ^R _3/ independently from each other, represent a C_x- C₃ alkyl group;

R₄ represents a hydrogen atom or a C_x-C₃ alkyl group; R_y represents a halogen atom, a Ci-C₄ alkyl group, a C_x-C₄ haloalkyl group, a C_x-C₄ alcoxy group, a C_x-C₄ haloalcoxy group ; n represents an integer ranging from 0 to 3 ; X represents a hydroxyl OH; a halogen atom; a C₁-C₄ alkoxy group; a phenoxy group; or an acyloxy group RCOO wherein R represents a Ci-C₄ alkyl group, or a phenyl optionally substituted by C₁-C₄ alkyl groups, C₁-C₄ haloalkyl groups or halogen atoms .

The reaction conditions for effecting the process described above, in which a benzoic acid or one of its corresponding halides, esters or anhydrides (possibly mixed) are reacted with an aniline, are widely described in chemical literature, for example in "Advanced Organic Chemistry", Jerry March, 4^a Edition, 1992, John Wiley & Sons Pub., pages 417-424 and references cited therein.

Various alternative reaction conditions can be selected, also in relation to the nature of the compound of general formula (II) ; for example, when X represents a halogen atom, preferably chlorine, the reaction is normally carried out in the presence of an inert solvent and in the presence of an organic or inorganic base, at a temperature ranging from -20⁰C to the boiling point of the reaction mixture.

Examples of solvents which can be used for the above reaction include water, aliphatic or cycloaliphatic hydrocarbons (petroleum ether, hexane, cyclohexane etc.), chlorinated hydrocarbons (methylene chloride, chloroform, carbon tetrachloride, dichloroethane, etc.), aromatic hydrocarbons (benzene, toluene, xylene, chlorobenzene, etc.), ethers (diethyl ether, diisopropyl ether, dimethoxyethane, dioxane, tetrahydrofuran, etc.), esters (ethyl acetate etc.), ketones (acetone, methylethyl- ketone, methylpropylketone , methylisobutyl ketone, etc.), nitriles (acetonitrile, benzonitrile, etc.), aprotic dipolar solvents (dimethylformamide, dimethylacetamide, hexamethylphosphorotriamide , dimethylsulphoxide , sulpholane, N-methylpyrrolidone, etc.).

Inorganic bases which can be used for the purpose are, for example, hydroxides, carbonates and bicarbonates of sodium or potassium.

Organic bases which can be used for the purpose are, for example, triethylamine, pyridine, 4 -N, N-dimethyl- aminopyridine , N,N-dimethylaniline, N-methylpiperidine, lutidine, diazabicyclooctane (DABCO) , diazabicyclononene

(DBN) , diazabicycloundecene (DBU) .

The intermediates having general formula (II) are compounds described in literature, in some cases commercially available, and in any case preparable according to the known methods.

The benzoic acids having formula (II) (X = OH) , for example, are described in "Beilsteins Handbuch der

Organischen Chemie" , 9, III, 1330, 1374; "Journal Organic

Chemistry", 26 (1961), 3208-3211; German patent Nr. DE 2060063.

The corresponding acid derivatives (esters, anhydrides, halides) can be easily prepared from them according to what is described, for example, in "Advanced Organic Chemistry", Jerry March, 4^a Edition, 1992, John Wiley & Sons Pub., pages 392-402, 437-438 and references cited therein. The intermediates of general formula (III) can be prepared for example according to what is described in European patent application EP 0654464.

As already mentioned, the compounds having general formula (I) have a particularly high fungicidal activity which is exerted with respect to numerous phytopathogenic fungi which attack important agricultural crops .

Examples of phytopathogenic fungi which can be effectively fought with the compounds of general formula (I) are those belonging to the groups of Basidiomycetes, Ascomycetes, Deuteromycetes or fungi imperfecti, Oomycetes: Puccinia spp., Ustilago spp., Tilletia spp., Uromyces spp., Phakopsora spp., Rhizoctonia spp., Erysiphe spp., Sphaerotheca. spp., Podosphaera spp., Uncinula spp., Helminthosporium spp., Rhynchosporium spp., Pyrenophora spp., Monilinia spp., Sclerσtinia spp., Septoria spp. (Mycosphaerella spp.), Venturia spp., Botrytis spp., Alternaria spp., Fusarium spp., Cercospora spp., Cercosporella herpotrichoides, Colletotrichum spp., Pyr±cularia oryzae, Sclerotium spp., Phytophtora spp., Pythium spp., Plasmopara viticola, Peronospora spp., Pseudoperonospora cubensis, Bremia lactucae.

The main crops which can be protected with the compounds of the invention comprise cereals (wheat, barley, rye, oats, rice, corn, sorghum, etc.), fruit plants (apple, pear, plum, peach, almond, cherry, banana, vines, strawberry, raspberry, blackberry, etc.), citrus trees (orange, lemon, mandarin, grapefruit, etc.), legumes (beans, peas, lentils, soybean, etc.), vegetables (spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, aubergines, peppers, etc.), cucurbitaceae (pumpkins, zucchini, cucumbers, melons, water-melons, etc.), oleaginous plants (sunflower, rape, peanut, castor-oil plant, coconut, etc.) tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton.

In particular, the compounds having general formula (I) have proved to be considerably effective in the control of Puccinia recondita, Helminthosporium teres, Septoria tritici e Fusarium spp. on cereals, and in the control of Phakopsora pachyrhizi on soya.

Furthermore, the compounds having general formula (I) are also effective in the control of bacteria and phytopathogenic viruses, such as for example Xanthomonas spp., Pseudomonas spp., Erwinia amylovora, the mosaic virus of tobacco.

The compounds of general formula (I) are capable of exerting a fungicidal action of both a curative and preventive nature and have a low or zero phytotoxicity.

A further object of the present invention therefore relates to the use of the benzamidic compounds having general formula (I) for the control of phytopathogenic fungi of agricultural crops .

For practical uses in agriculture, it is often preferable to use fungicidal compositions containing compounds of the invention suitably formulated.

A further object of the present invention relates to fungicidal compositions comprising one or more benzamidic compounds having general formula (I) , a solvent and/or solid or liquid diluent, possibly a surfactant. The above fungicidal compositions can be used in the form of dry powders, wettable powders, emulsifying concentrates, emulsions, micro-emulsions, pastes, granulates, water dispersible granules, solutions, suspensions, etc.: the choice of the type of composition will depend on the specific use.

The fungicidal compositions are prepared in the known way, for example by diluting or dissolving the active substance with a solvent medium and/or a solid or liquid diluent, possibly in the presence of surfactants. Solid diluents or supports which can be used for example are: silica, kaolin, bentonite, talc, infusorial earth, dolomite, calcium carbonate, magnesia, gypsum, clays, synthetic silicates, attapulgite, sepiolite.

Solvents or liquid diluents which can be used, are for example, in addition to water, aromatic organic solvents (xylols or blends of alkylbenzols, chlorobenzene, etc.), paraffins (petroleum fractions), alcohols (methanol, propanol, butanol, octanol, glycerine, etc.), esters (ethyl acetate, isobutyl acetate, alkyl carbonates, alkyl esters of adipic acid, alkyl esters of glutaric acid, alkyl esters of succinic acid, alkyl esters of lactic acid, etc.), vegetable oils (rape oil, sunflower oil, soybean oil, castor oil, corn oil, peanut oil, and their alkyl esters) , ketones (cyclohexanone, acetone, acetophenone, isophorone, ethylamylketone , etc.), amides (N, N-dimethyIformamide, N- methylpyrrolidone, etc.), sulphoxides and sulphones (dimethylsulphoxide, dimethylsulphone, etc.), and mixtures thereof.

Sodium salts, calcium salts, potassium salts, salts of triethylamine or triethanolamine of alkylnaphthalene- sulphonates, polynaphthalenesulphonates, alkyl sulphonates, aryl sulphonates, alkylaryl sulphonates, polycarboxylates, sulphosuccinates, alkyl sulpho- succinates, ligninsulphonates, alkyl sulphates, can be used as surfactants; as also polyethoxylated fatty alcohols, polyethoxylated alkylphenols, polyethoxylated esters of sorbitol, polypropoxy polyethoxylates (block polymers) .

The fungicidal compositions can also contain special additives for particular purposes, such as for example, antifreeze agents such as propylene glycol, or adhesion agents, such as Arabic gum, polyvinyl alcohol, polyvinyl pyrrolidone, etc. When desired, other compatible active principles can be added to the fungicidal compositions containing the compounds of general formula (I) , such as, for example, fungicides different from those having general formula (I), phytoregulators, antibiotics, herbicides, insecticides, fertilizers and/or mixtures thereof. Examples of fungicides different from those having general formula (I) , that may be included in the fungicidal compositions object of the present invention are.- acibenzolar, amisulbrom, ampropylfos, anilazine, azaconazole, azoxystrobin, benalaxyl, benalaxyl-M, benomyl, benthiavalicarb, bitertanol, bixafen, blasticidin-S, boscalid, bromuconazole, bupirimate, buthiobate, captafol, captan, carbendazim, carboxin, carpropamid, chinomethionat, chloroneb, chlorothalonil, chlozolinate, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, debacarb, dichlofluanid, dichlone, diclobutrazol, diclomezine, dicloran, diclocymet, diethofencarb, difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole, dinocap, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, edifenphos, epoxiconazole, etaconazole, ethaboxam, ethirimol, ethoxyquin, etridiazole, famoxadone, fenamidone, fenaminosulf , fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fentin, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, flumorph, fluopicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, . flutriafol, folpet, fosetyl-aluminium, fuberidazole, furalaxyl, furametpyr, furconazole, furconazole-cis, guazatine, hexaconazole, hymexazol, hydroxyquinoline sulphate, imazalil, imibenconazole, iminoctadine, ipconazole, iprobenfos, iprodione, IR5885 (proposed ISO name: valifenalate) isoprothiolane, iprovalicarb, isopyrazam, isothianyl, kasugamycin, kresoxim-methyl, mancopper, mancozeb, mandipropamid, maneb, mebenil, mepanipyrim, mepronil, meptyldinocap, metalaxyl, metalaxyl-M, metconazole, methfuroxam, metiram, metominostrobin, metrafenone, metsulfovax, myclobutanil, natamycin, nicobifen, nitrothal-isopropyl, nuarimol, ofurace, orysastrobin, oxadixyl, oxpoconazole, oxycarboxin, pefurazoate, penconazole, pencycuron, pentachlorofenol and its salts, penthiopyrad, phthalide, picoxystrobin, piperalin, Bordeaux mixture, polyoxins, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, proquinazid, prothiocarb, prothioconazole, pyracarbolid, pyraclostrobin, pyrazophos, pyribencarb, pyrifenox, pyrimethanil, pyroguilon, pyroxyfur, quinacetol, quinazamid, quinconazole, quinoxyfen, quintozene, rabenzazole, copper hydroxide, copper oxychloride, copper (I) oxide, copper sulphate, sedaxane, silthiofam, simeconazole, spiroxamine, streptomycin, tebuconazole, tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide, thiophanate, thiophanate-methyl, thiram, tiadinil, tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triarimol, triazbutil, triazoxide, tricyclazole, tridemorf, trifloxystrobin, triflumizole, triforine, triticonazole, uniconazole, uniconazole-P, validamycin, vinclozolin, zineb, ziram, sulphur, zoxamide . The concentration of benzamidic compounds having general formula (I) in the above compositions can vary within a wide range; it generally ranges from 1% to 90%, preferably from 5% to 50%.

The application of these compositions can be effected on all parts of the plant, for example on the leaves, stems, branches and roots, or on the seeds themselves before sowing, or on the ground in which the plant grows .

A further object of the present invention therefore relates to a method for the control of phytopathogenic fungi in agricultural crops, which consists in the application of effective dosages of the compounds of formula (I) , used as such or formulated in fungicidal compositions as described above. The amount of compound to be applied for obtaining the desired effect can vary in relation to different factors, such as, for example, the compound used, the crop to be preserved, the type of pathogen, the degree of infection, the climatic conditions, the application method, the formulation adopted.

Doses of compound ranging from 10 g to 5 kg per hectare of agricultural crop generally provide a sufficient control.

The following examples are provided for a better understanding of the invention for illustrative and non- limiting purposes of the same. EXAMPLE 1

Preparation of N- (1, 1, 3-trimethyl-4-indanyl) -2-fluoro- 6- trifluoromethylbenzamide (compound P-I)

1) Synthesis of 1, 2 , 3, 4-tetrahydro-2, 2, 4-trimethyl- quinoline 7.4 g of palladium on carbon at 10% are added to a solution of 74 g of 1, 2-dihydro-2 , 2, 4-trimethylquinoline

(prepared according to what is described in Organic

Synthesis Coll. Vol. 3, page 329) in 225 ml of ethyl acetate and the mixture is kept under stirring in an atmosphere of H₂ at room temperature for 15 h.

At the end, the mixture is filtered on a celite bed and is concentrated at reduced pressure; 74 g of 1,2,3,4- tetrahydro-2 , 2, 4-trimethylquinoline are obtained. 1H NMR (200Mhz, CDCl₃) δ at: 0.95 (3H,s), 1.24 (3H,s), 1.38 (3H,d), 1.46 (IH, dd), 1.76 (IH, dd), 2.95 (IH, m), 3.6-3,8 (INH), 6.40-7.25 (4H,m).

2) Synthesis of 1, 1, 3-trimethyl-4-aminoindane 88 g of 2-chloropropionic anhydride, prepared according to what is described in European patent application EP 0654464, are added to 52.15 g of 1,2,3,4- tetrahydro-2 , 2 , 4-trimethylquinoline; the mixture is kept under stirring at 105⁰C for 8 h in a nitrogen atmosphere.

The mixture is cooled to room temperature, 92 ml of sulphuric acid at 98% are added and the mixture is heated to 60⁰C for 30 minutes. After cooling, 92 ml of water and

23 ml of acetic acid are added and the mixture is heated to reflux temperature for 3 hours.

The mixture is carefully treated with water and aqueous ammonia and extracted with ethyl acetate. The organic phase is then dried on sodium sulphate and concentrated at reduced pressure. The raw product thus obtained is purified on a chromatographic column (eluent hexane/ethyl acetate 8/2) to obtain 40 g of the desired product.

¹H NMR (200 Mhz, CDCl₃) δ at: 1.24 (3H,s), 1.35 (3H,s), 1.38 (3H,d), 1.62 (IH, dd), 2.23 (IH, dd), 3.26 (lH,m) , 3.64 (2H, bs) , 6.45-7.05 (3H,m).

3) Synthesis of N- (1, 1, 3-trimethyl-4-indanyl) -2-fluoro- 6-trifluoromethylbenzamide

2.8 ml of triethylamine are added dropwise to a solution of 3 g of 1, 1, 3-trimethyl-4-aminoindane and 3.9 g of 2-fluoro-6-trifluoro-methylbenzoyl chloride in 6 ml of methylene chloride.

After 2 hours at room temperature, the mixture is treated with diluted HCl, the phases are separated and the aqueous phase is extracted with methylene chloride .

The organic phase is dried on sodium sulphate and concentrated at reduced pressure. The raw material thus obtained is purified on a chromatographic column (eluent hexane/ethyl acetate 8/2) to obtain 6 g of the desired product.

¹H NMR (200 Mhz, CDCl₃) δ at: 1,24 (3H,s), 1,35 (3H,s),

1,37 (3H,d), 1,62 (IH, dd), 2,21 (IH, dd), 3,25 (IH m) , 6,10 (IH, bs) , 6,95-7,9 (6H,m).

EXAMPLE 2

Determination of the preventive fungicidal activity against wheat rust (Puccinia recondita) .

Leaves of wheat plants (cultivar Gemini) , grown in vases in a conditioned environment (20+1⁰C, 70% of relative humidity) are treated, by spraying on both sides of the leaves, with hydroacetonic dispersions (at 20% v/v of acetone and containing 0.3% of Tween 20) of the products under testing. After remaining 5 days in a conditioned environment, the plants are sprayed on both sides of the leaves with an aqueous suspension of conidia of Puccinia recondita

(200,000 conidia per ml).

The plants are maintained in a humidity-saturated environment at a temperature ranging from 18 to 24⁰C for the incubation period of the fungus.

At the end of this period (14 days) , the fungicidal activity is evaluated according to an evaluation percentage scale from 0 (completely infected plant) to

100 (healthy plant) .

Table 1 indicates the activity data obtained with the compound P-I of Example 1, compared with the following known reference compounds of the prior art:

RCl: N- (1, 1, 3-trimethyl-4-indanyl) -2-trifluoromethyl- benzamide, compound Nr. 17 of EP 0086111 and Nr. 1 of

Japanese patent application Nr. JP59144744; RC2 : N- (1, 1-dimethyl-4 -indanyl) -2-fluoro-6-trifluoro- methylbenzamide, compound Nr. 1 of Japanese patent No

JP61280460.

The table also indicates the phytotoxicity of the compounds with respect to the crop, according to the following scale:

- : non-phytotoxic product;

+ : slightly phytotoxic product;

+ : phytotoxic product .

Table. Fungicidal activity in greenhouses against Puccinia recondita on wheat.

Claims

1. Benzamide compound of general formula (I)

(I)

in which:

R_x represents a halogen atom or a methyl group optionally substituted by fluorine atoms,- Ri, R₂, R₃, independently from each other, represent an alkyl group Ci-C₃;

R₄ represents a hydrogen atom or a C_x-C₃ alkyl group;

R_y represents a halogen atom, an alkyl group C_x-C₄, a haloalkyl group C_x-C₄, an alkoxy group Ci-C₄, a haloalkoxy group C₁-C₄,- n represents a variable integer between 0 and 3.

2. Compounds according to claim 1, wherein the fluorine atom F is in ortho position to the benzamide group and/or R_x is a trifluoromethyl and/or Ri, R₂ and R₃ represent a methyl and/or R₄ is a hydrogen atom.

3. Compounds according to claim 1, selected from: N- (1, 1, 3-trimethyl-4-indanyl) -2-fluoro-6-trifluoro- methylbenzamide ,-

N- (1,1, 3-trimethyl-4-indanyl) -4-fluoro-6-trifluoro- methylbenzamide ;

N- (1, 1, 3-trimethyl-4-indanyl) -2-fluoro-6 -methyl- benzamide ;

N- (1,1, 3-trimethyl-4-indanyl) -3-fluoro-2-methyl- benzamide ;

N- (1, 1, 3-trimethyl-4-indanyl) -2-fluoro-6-difluoro- methylbenzamide ;

N- (1,1, 3-trimethyl-4-indanyl) -4-fluoro-6-difluoro- methylbenzamide ; N- (1, 1, 3-trimethyl-4-indanyl) -2, 6-difluorobenzamide;

N- (1,1, 3-trimethyl-4-indanyl) -2-fluoro-6-iodo-benzamide; N- (1, 1, 3-trimethyl-4-indanyl) -2-chloro-6-fluorobenzamide ; preferably N- (1, 1, 3-trimethyl-4-indanyl) -2-fluoro-6- trifluoro-methylbenzamide .

4. Fungicide compositions comprising one or more benzamide compounds of general formula (I) according to any one of the previous claims, a solvent and/or solid or liquid diluent, optionally a surfactant.

5. Compositions according to claim 4, also comprising active ingredients compatible with the compounds of general formula (I) , as fungicides different from the benzamide compounds of general formula (I) , plant growth regulators, antibiotics, herbicides, insecticides, fertilisers and/or mixtures thereof.

6. Compositions according to claim 4 or 5, wherein the concentration of benzamide compounds of general formula (I) is between 1 and 90%, preferably between 5 and 50%.

7. Use of the benzamide compounds of general formula (I) according to any one of claims 1 to 3 , for controlling crop phytopathogenic fungi .

8. Use according to claim 7, wherein the phytopathogenic fungi belong to one or more of the following classes: Basidiomycetes, Ascomycetes, Deuteromycetes or fungi imperfecti, Oomycetes .

9. Use according to claim 7 or 8 , wherein the crops are selected from the group comprising cereals, fruit plants, citrus trees, legumes, vegetables, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton.

10. Use according to claim 7, for controlling Puccinia recondita, Helminthosporium teres, Septoria tritici and

Fusarium spp. on cereals or for controlling Phakopsora pachyrhizi on soybean.

11. Use of benzamide compounds according to any one of claims 1 to 3 for controlling bacteria and phytopathogenic viruses.

12. Method for controlling phytopathogenic fungi in crops, which consists of applying effective doses of the benzamide compounds of general formula (I) according to any one of claims 1 to 3 , in quantities of between 10 g and 5 kg per hectare of crops.