AMINOBUTYRIC ACID FUNGICIDES

Abstract: Novel aminobutyric acids derivatives and methods for protecting crops against fungal diseases by applying to the crops or their locus a composition containing an effective amount of said derivatives.

Description: AMINOBUTYRIC ACID FUNGICIDES INTRODUCTION The present invention concerns a novel method to protect plants from pathogenic attack. BACKGROUND OF THE INVENTION The use of threo-DL-β-methylaspartic acid and of DL-β-aminobutyric acid for the control of root rot of peas caused by Aphanomyces euteiches Drechs, has been described (Papavizas, Plant Disease Reporter, 48, 537-541 (1964), Papavizas, Plant Disease Reporter. 51. 125-129 (1967). The use of D-alaninie, D-and DL leucine and DL-α-aminobutyric acid at 0.03 M was described to reduce scab in apple caused by Venturia inaequalis (Kuc et al.. 49: 313-315, 1959). Van Andel, showed (Tijdschur. Plantenziekten. 64 307-327, 1958) that DL-serine, D-serine (and to a lesser extent L-serine), phenylserine, DL-threonine but not DL-α aminobutyric acid nor DL-β aminobutyric acid behaved as chemothrerpeutants against the fungus cladosporium cucumerinum on cucumber (Ibid, page 318). Oort and Van Andel (1960, Mededel. Landsborowhager school Dpzoekingssta. Staat Gent 25: 981-992) showed that DL-β- arninobutyric acid applied to leaves of tomato protected those leaves against Phvtophthora infestans (page 987). Various derivatives of DL-β-aminobutyric acid and β-aminocrotonic acid have been described in the patent literature as fungicides against Phvtophthora infestans in tomato and Plasmopara viticola in grapes (German Patent No. 1,120,802). Co-pending Israel Patent Application No. 111,824 describes the preparation and use of similar compounds which induce local and systemic resistance of crops against fungal diseases. OBJECTIVES OF THE INVENTION It is the objective of the present invention to provide compounds having improved activity against fungi as compared with the compounds of the co-pending Israel patent application 111,824. SUMMARY OF THE INVENTION We have found novel compounds of the formula (I): wherein: Ri and R 2 are independently hydrogen, Cι- 8 alkyl, phenyl, and phenyl Cι- alkyl R 3 is Cι- 23 straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyl; halogenated alkyl, phenyl, or benzyl; alkyl phenyl; R t and R 5 are independently hydrogen or Cι- 8 alkyl; Re is hydrogen; Cι- 8 alkyl; C 2 - 8 alkanoyl; phenyl C1-4 alkyl, benzoyl wherein the phenyl moiety is optionally substituted by one or more halogen atoms or alkyl groups C 2 - 8 alkoxycarbonyl; CONHRg wherein Rg is hydrogen, Cι- 8 alkyl, phenyl, phenyl Cι- 4 ; phenyl C 2 - 4 alkyloxycarbonyl; R 7 is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; X is O or NH and salts thereof; and the crop is selected from tomatoes, potatoes, cereals, grapes, melon, wheat and cucumber. We have also found a novel method of protecting a crop against fungal diseases caused by fungi by applying to the crop or its locus a composition containing an effective amount of a compound of the formula (I). DETAILED DESCRIPTION OF THE INVENTION Alkyl as used herein refers to straight chains, branched and cyclic forms and preferably contain one to ten carbon atoms. Ri and R 2 are preferably independently hydrogen, methyl or phenyl, more preferably R\ is hydrogen or methyl and R is hydrogen. R 3 is preferably Cι- 1 straight or branched or a cyclic alkyl or alkenyl, phenyl, benzyl, or alkyl phenyl. » and R 5 are preferably independently hydrogen or C1-4 alkyl, more preferably R 4 is hydrogen or methyl and R5 is hydrogen. R« is preferably hydrogen, C 1 - 5 alkyl; and most preferred hydrogen methyl. R 7 is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl. Preferred compounds of the invention are: D,L N-benzenesulfonyl-3 -aminobutyranilide; D,L-N-p-methylbenzoyl-3 -aminobutyric acid n-octyl ester; N-p-methylbenzoyl-3 -aminobutyric acid sec butyl ester; D,L-N-3,4-dichloro benzoyl-3 -aminobutyric acid n-octyl ester; D,L-N-4-chlorobenzoyl-3 -aminobutyric acid-2-chloro ethyl ester; D,L-N-benzensulfonyl-3-amino N-benzyl butyramide; D,L-N-benzoyl-3 -aminobutyric acid 2-chloroethyl ester: N-p-methylbenzoyl~3-amiobutyric acid 1 -methyl- 1-pentyl ester; D,L-N-benzenesulfonyl-3-aminobutyric acid, n-octyl ester; N-benzenesulfonyl-3 -aminobutyric acid-sec-butyl ester; N-benzenesulfonyl-3 -aminobutyric acid- 1 -methyl- 1 -butyl ester; D,L N-4-methoxybenzoyl-3 -aminobutyric acid heptyl ester D,L N-3, 5 -dimethylbezoyl-3 -aminobutyric acid heptyl ester D,L N-2,6-difluorobenzoyl-3-aminobutyric acid heptyl ester D,L N-4-tertbutylbenzoyl-3 -aminobutyric acid heptyl ester D,L N-4-methylbenzenesulfonyl-3 -aminobutyric acid 1-methylpentyl ester D,L N-benzenesulfonyl-3 -aminobutyric acid 3-phenylpropyl ester D,L N-4-cholrobenzoyl-3 -aminobutyric acid 1-methylpentyl ester D,L N-benzenesulfonyl-3 -aminobutyric acid 2-(trichloromethyl)ethyl ester D,L N-4-methylbenzenesulfonyl-3-aminobutyric 1-methylpropyll ester D,L N-3 ,4-dimethylbezoyl-3 -aminobutyric acidl-methylbutyl ester D,L N-3 -methylbezoyl-3 -aminobutyric acid heptyl ester D,L N-3, 5 -dimethylbezoyl-3 -aminobutyric acid 1-methylpentyl ester D,L N-2,6-dichlorobenzoyl-3-aminobutyric acid heptyl ester D,L N-2,6-dichlorobenzoyl-3-aminobutyric acid 1-methylpentyl ester D,L -4-methylbenzoyl-3 -aminobutyric acid 3-phenylpropyl ester D,L N-3,5-dimethylbezoyl-3-aminobutyric acid 2-chloroethyl ester D,L N-4-methoxybenzoyl-3 -aminobutyric acid 2-chloroethyl ester D,L N-benzoyl-3 -aminobutyric acid 2-(trichloromethyl)ethyl ester D,L N-4-cholrobenzoyl-3 -aminobutyric acid heptyl ester D,L N-benzenesulfonyl-3 -aminobutyric acid l-methyl-2-rnethoxyethyl ester D,L N-2-methylbezoyl-3 -aminobutyric acid heptyl ester D,L N-4-methylbenzenesulfonyl-3 -aminobutyric acid 2-bromoethyl ester D,L N-4-methylbenzenesulfonyl-3 -aminobutyric acid heptyl ester D,L N-4-chlorobenzenesulfonyl-3 -aminobutyric acid propyl ester D,L N-4-methylbenzoyl-3-aminobutyric acid 2-(trichloromethyl)ethyl ester D,L N-4-methylbenzoyl-3 -aminobutyric acid cyclohexyl ester D,L N-benzoyl-3 -aminobutyric acid cyclohexyl ester D,L N-benzenesulfonyl-3 -aminobutyric acid cyclohexyl ester D,L N-4-chlorobenzenesulfonyl-3 -aminobutyric acid heptyl ester D,L N-benzenesulfonyl-3-aminobutyric acid propyl ester D,L N-benzoyl-3 -aminobutyric acid 2-propenyl ester D,L N-4-methylbenzoyl-3-aminobutyric acid 1-methylhexyl ester D,L N-4-methylbenzoyl-3-aminobutyric acid 1-methyldecanyl ester D,L N-3 ,4-dimethylbezoyl-3 -aminobutyric acid heptyl ester D,LN-4-methylbezoyl-3 -aminobutyric acid 1-methylpentyl ester D,L N-2-methylaminobenzoyl-3 -aminobutyric acid methyl ester. D,L N-4-chlorobenzensulfonyl-3 -aminobutyric acid 1-methylpentyl ester D,L N-benzensulphonyl-3 -aminobutyric acid 3-phenylpropyl ester D,L N-2-methylaminobenzoyl-3 -aminobutyric acid 1-methylpentyl ester D,L N-benzensulfonyl -3 -aminobutyric acid 3,5-dichlorophenyl ester D,L N-4-2-thiophenebenzoyl-3-aminobutyric acid octyl ester D,L N-4-2-thiophenebenzoyl-3 -aminobutyric acid 1-methylpentyl ester D,L N-3 ,4-dimethylbenzoyl-3 -aminobutyric acid octyl ester Production methods The novel compounds encompassed by the present application are structurally related to known compounds and can be easily prepared by either derivatising the known compounds or by modifying the procedures for preparing the known compound, as required. These procedures will be apparent to those skilled in the art. The following procedures are illustrative. Compounds of the formula (I) wherein R x and R 2 and R 4 - 7 are as previously defined and R 3 represents hydorgen or d-s alkyl can be obtained from β-aminobutyric acid. To prepare compounds of formula (I) where Re and R 7 are as previously defined β-aminobutyric acid is reacted with NR 7 H 2 , wherein R 7 is as previously defined. Reactions of this type are described in the literature, e.g., by A. Zilkha and J. Rivilin, J. Org. Chem. 1957, 23, 94. The present compounds were found to be effective against late blight in potato and tomatoes, powdery mildew in cereals, downy meldow in cucumber, melon and grapes. The present compounds of this invention will typically be applied to crops or their locus before or after the onset or after the initial signs of fungal attack and may be applied to the foliar surfaces of the crop. The amount of active ingredient to be employed will be sufficient to induce the systemic resistance of the crop to control the fungi and will vary depending on such factors as the species of fungi to be controlled, the type of treatment (for example, spraying dusting, seed treatment, soil drench), the condition of the crop, and the particular active ingredient used. As an application to the crop or its locus, the compounds will be applied to the crops with a dosage rate of from 0.1 to 5 kg/ha, preferably from 0.2 to 2kg/ha. with application being repeated as necessary, typically at intervals of every one to three weeks. Depending on circumstances, the compounds of this invention may be used in association with other pesticides, e.g., fungicides, insecticides, acaricides, herbicides, or plant growth regulating agents in order to enhance their activity or to widen their spectrum of activity. The compounds of this invention are conveniently employed as fungicidal composition in association with agriculturally acceptable carriers or diluents. Such compositions also form part of the present invention. They may contain, aside from a compound of formula (I) as active agent, other active agents, such as fungicides. They may be employed in either solid or liquid application forms e.g., in the form of a wettable powder, an emulsion concentrate, a water dispersible suspension concentrate ("flowable"), a dusting powder, a granulate, a delayed release form incorporating conventional carriers, diluents and/or adjuvants. Such compositions may be produced in conventional manner, e.g. by mixing the active ingredient with a carrier and other formulating ingredients. Particular formulations to be applied in spraying forms such as water dispersible concentrates or wettable powders may contain surfactant such as wetting and dispersing agents, e.g., the condensation product of formandehyde with naphthalene sulphonate, an alkyl-aryl-sulphonate, a lignin sulphonate, a fatty alkyl sulphate an ethoxylated alkylphenol and an ethoxylated fatty alcohol. In general, the formulations include from 0.01 to 90% by weight of active agent, said active agent consisting either of at least one compound of formula (I) or mixture thereof with other active agents, such as fungicides. Concentrated forms of compositions generally contain between about 2 and 80%, preferably between about 5 and 70% by weight of active agent. Application forms of formulation may, for example, contain from 0.01% to 20% by weight, preferably from 0.01% to %5 by weight, of active agent. Formulation Example I: Wettable powder 50 parts by weight of a compound of formula (I) are ground with 2 parts of lauryl sulphate, 3 parts sodium lignin the sulphonate and 45 parts of finely divided kaolininite until the mean particle size is below 5 microns. The resulting wettable powder so obtained is diluted with water before use to a concentration of between 0.01% to 5% active ingredient. The resulting spray liquor may be applied by foliar spray as well as by root drench application. Formulation Example II: emulsion concentrate 25 parts by weight of a compound of formula I, 65 parts of xylene, 10 parts of the mixed reaction product of an alkylphenol with xyleneoxide and calcium-dodecyl -benzene sulphonated are thoroughly mixed until a homogeneous solution is obtained. The resulting emulsion concentrate is diluted with water before use. Formulation Example III: Granulate (for soil treatments) Onto 94.5 parts by weight of quartz sand in a tumbler mixer is sprayed 0.5 parts by weight of a binder (non-ionic tenside) and is thoroughly mixed. 5 parts by weight of compound of the formula (I) in powdered form are then added and thoroughly mixed to obtain a granulated formulation with a particle size in the range of from about 0.3 to about 0.7 mm. The granulate may be applied by incorporation into the soil adjacent the plants to be tested. Formulation Example IV: Seed or Tuber Dressing 25 parts by weight of compound of the formula (I), 15 parts of dialkylphenoxy-poly- (ethylenoxy) ethanol, 15 parts of fine silica, 44 parts of fine kaolin, 0.5 parts of a colorant (e.g., crystal violet) and 0.5 parts of xantham gum are mixed and ground in a contraplex mill at approximately 10,000 rpm to an average particle size of below 20 micron. The resulting formulation is applied to the seeds or tubers as an aqueous suspension in an apparatus suitable for that purpose. Where the compound of the formula (I) is liquid, it is first absorbed on the carriers, if desired with the aid of a small amount of a volatile solvent such as acetone. The resulting powder if first allowed to dry if a solvent is used, then the other ingredients are added and the rest of the procedure is carried out. Formulation Example V: Soil Drench Drip Irrigation 2 parts by weight of compound of the formula (I) are dissolved in 1,000 parts of water. The resulting formulation is applied to plant by drip irrigation. As previously mentioned, the compounds of formula (I) are effective in activation or enhancing a corp's defense system against fungal diseases caused by fungi. Such activity can be demonstrated in usign the general procedures of the following tests: While the invention will now be described in connection with certain preferred embodiments in the following examples, it will be understood that it is not intended to limit the invention to these particular embodiments. On the contrary, it is intended to cover all alternatives, modifiations and equivalents as may be included within the scope of the invention as defined by the appended claims. Thus, the following examples, which include preferred embodiments, will serve to illustrate the practice of this invention, it being understood that the particulars shown are by way of example and for purpses of illustrative discussion of preferred embodiments ofthe present invention only and are presented in the cause of providing what is believed to be the most useful and readily understood description of procedures, as well as ofthe principles and conceptual aspects ofthe invention. EXAMPLES Example 1: D.L-N-benzenesulfonyl-3 -amino. N-benzyl butyramide To 6.0gr β-Aminobutyric acid in 20ml water was added 5.4gr NaOH dissolved in 26ml water. 10.3gr Benzenesulfonyl chloride in 36ml Dichloroethane was added at r.t. during 15 minutes. The mixture was stirred for 10 minutes at r.t. and heated at 68°C during 4 hr. The phases were separated, and the aqueous one, was acidified with HCl (cone) to pH 2.5. After extrcation with Dichloroethane (DCE) DL-N-benzenesulfonyl-3 aminobutyric acid (I) crystallized from the organic phase. 6.7gr m.p. 125-127. 4°C. To 7.7 gr compound I, in 80ml Dichloroethane, was added 7.5gr PCI5 in small portions, keeping the mixture temperature at 5°C. The mixture was allowed to warm to r.t. and stirred during 6 hr. Petrol ether 60-80 (400ml) was added, the chloride was filtered and dried yielding 7.3gr product (II). To 3.0gr ofthe acid chloride (II) in 30ml DCE, was added 2.3gr benzylamine in 5ml DCE during 10 minutes at 10-15°C. The mixture was heated to 50°C during 7 hr. 30ml of water was added, the organic pahse separtated, and after concentration ofthe solution the product precipitated. 2.66gr m.p. 105-107°C. NMR and MS spectrocopic methods confirmed the structure. Example 2: D.L-N-benzensulfonyl-3-aminobutyranilide To 3.0gr Acid chloride (II) in 30ml DCE was added 2.0gr aniline in 5ml DCE during 10 minutes at 10-15°C. The mixture was heated at 50°C during 7 hr. 30ml of water was added, and the organic phase was separated. Evaportaion ofthe solvent gave 3.5gr product. Recrystallization from toluene gave 2.7gr mp. 130-132°C. NMR and MS spectroscopic methods confirmed the structure. Example 3: D,L-N-p-methyl benzoyl-3 -aminobutyric acid n-octyl ester To 2.Ogr β-Aminobutyric acid in 9ml water, was added 3.4gr NaOH in 9 ml water. 3.Ogr of p- Toluoyl chloride in 15ml DCE was added during 20 minutes at r.t. The mixture was heated at 62° C during 7hr. The phases were separated, and the aqueous one was acidified with HCl (cone) to pH 2.0-2.5. The compound precipitated; decantation and recrystallization with water gave after trituration with DCE, 3.3gr. m.p. 115-118°C, of D,L-p-methylbenzoyl-3- aminobutyric acid (IU). to 3.0 gr ofthe acid (III) in 35 ml DCE, was added 3.2. gr PC1 5 in small portions, keeping the mixture temperature at 10-15 °C. The mixture was allowed to warm to 25°C and was stirred for 7hr. Petrol ether 60-80 (280 ml) was added and oil was separted. Decantation ofthe solvent and addition of 50ml Petrol ether gives a crystaline compound. After filtration we obtain 2.5 gr acid chloride IV. To the chloride IV in 25ml DCE was added 4. lgr n-octanol in 5ml DCE during 20 minutes at 30°C. The mixture was heated at 65°C during 6 hr. Afte distillation, 25ml DCE was added, washed with 3X10ml sodium bicarbonate 2% and dired over MgSO 4 . Evaporation ofthe solvent gave 2. lgr m.p. 41-42°C ofthe product. NMR and MS confirmed the structure. Example 4: N-p-methyl benzoyl-3 aminobutyric acid-sec, butyl ester Method A To 2.6gr chloride IV in 25ml DCE, was added 2.3gr 2-butanol in 5ml DCE, during 10 minutes at 25°C. The mixture was heated at 65°C during 6 hr. After distillation, 25ml DCE was added, washed with sodium cicarbonate 2% and dried over MgSO 4 . Evaporation ofthe solvent gave 2.2gr ofthe product. NMR and MS spectroscopic methods confirms the structure. Method B The mixture of 2.0gr D,L-p-methylbenzoyl-3-aminobutyric (III) 0.85gr 2-butanol, 30ml Toluene and 0.04gr H2SO4 (cone) was heated under reflux for ca 7hr. The water formed in the reaction was separated by azeotropic distillation. The cooled reaction mixture was washed twice with 15ml water, sodium bicarbonate 2% and dried over MgSO 4 . Distillation ofthe solvent yield 1.7gr of the ester. Example 5: D.L-N-3-4-dichlorobenzoyl-3 -amino butyric acid n-octyl-ester D,L-N-3,4-dichlorobenzoyl-3-aminobutyric acid n-octyl ester To 1.5gr β-Aminobutyric acid in 5ml water, was added 2.5gr NaOH in 6.4. ml water. 3.0 gr of 3,4-dichloro benzoyl chloride in 10ml DCE was added during 10 minutes at r.t. The mixture was heated at 65°C during 6.5 hr. The phases were separated. The aqueous phase was washed twice with 15ml DCE and acidified with HCl (cone) to pH 1.5-2.0. The compound was filtered. 3. lgr mp 143-146°C (V) were obtained. To 2.5gr compound V in 35ml dichloroethane (DCE), was added 2.2gr PCI5 in small portions, keeping the mixture temperature at 10-15 °C. The mixture was allowed to warm to 25 °C, and stirred for 7hr. Petrol ether 60-80 was added, the acid chloride precipitated, filtered and dried, yielding 1.5gr. To the chloride in 25ml DCE was added 2.0gr n-octanol in 5ml DCE during 10 minutes at 20°C. The mixture was heated at 65°C during 7hr. After distillation, 25ml DCE was added, washed with sodium bicarbonate 2% and dried over MgSO 4 . Evaporation ofthe solvent gave 2.0gr ofthe titled compound. NMR and MS spectroscopic methods confirmed the sturcture. Example 6: D.L-N-4-chlorobenzoyl-3 -aminobutyric acid 2-chloro-ethyl ester D.L-N-4-chlorobenzoyl-3 -aminobutyric acid-2-chloro-ethyl ester To 3.0gr β-Aminobutyric acid in 7ml water, was added 3.4gr NaOH in 8.7ml water. 3. lgr of p- chlorobenzoyl chloride in 15ml DCE was added during 15 minutes at 10-15 °C. The mixture was heated at 60°C during 7hr. The phases were separated, and the aqueous phase was washed twice with 15ml DCE, and acidified with HCl (cone) to pH 1.5-2.0. The compound was filtered and recristallized with water. 3.94gr of DL-P-Chlorobenzoyl-3 aminobutyric acid (VI) was obtained. To 3.0gr of acid VI in 25ml Dee, was added 2.93gr PCI 5 in small portions, keeping the mixture temperature at 8-10°C. The mixture was allowed to warm to 25-27°C and stirred for 7hr. Petrol ether 60-80 (150ml) was added, the chloride was filtered and dried yielding 2.7gr (Vϋ). To 2.5gr of acid chloride VII in 20ml DCE was added 2-chloroethanol in 5.0ml DCE during 10 minutes at 15-17°C. The mixture was heated at 65°C during 7hr. After distillation 35ml DCE was added, and washed with sodium bicarbonate 2%. Evaporation ofthe solvent gave 1.73gr product. Crystallization from cyclohexane yield 0.5gr. mp 80-81°C. NMR and MS spectroscopic methods corifirmed the sturcture. Example 7: DL-N-benzenesulfonyl-3-aminobutyric acid n-octyl ester DL-N-benzenesulfonyl-3 -aminobutyric acid n-octyl ester The mixture of 2.0gr DL-N benzensulfonyl-3 aminobutyric acid (I), 1.78gr n-octanol, 30 ml Toluene and 0.04gr H 2 SO4 (cone) was heated under refulux for ca 3 hr. The water formed in the reaction was separated by azeotropic distillation. The cooled reaction mixture was washed twice with bicarbonate 2%, and dried over magnesium sulfate. Distillation ofthe solvent and alcohol yield 2.0 gr product, confirmed by spectroscopy. Example 8: N-benzenesulfonyl-3 -aminobutyric acid-sec butyl ester N-benzenesulfonyl-3 -aminobutyric acid-sec butyl ester The mixture of 2.0gr DL-N benzensulfonyl-3 aminobutyric acid (I), l.Ogr 2-butanol, 30 ml toluene and 0.04gr H 2 SO4 (cone) was heated under reflux for ca 6 hr. The water formed in the reaction was separated by azeotropic distillation. The cooled reaction mixture was washed twice with bicarbonate 2%, and dried over magnesium sulfate. Distillation ofthe solvent and alcohol yield 1.8gr procuct, confirmed by spectroscopy. Example 9: N-benzenesulfonyl-3 -aminobutyric acid 1 -methyl- 1 -butyl ester N-benzenesulfonyl-3-aminobutyric acid 1 -methyl- 1 -butyl ester The mixture of 2.0gr DL-N benzensulfonyl-3 aminobutyric acid (I), 1.2gr 2-Pentanol, 30 ml toluene and 0.04gr H 2 SO (cone) was heated under reflux for ca 6hr. The reaction was treated as in the previous example. 2.0gr ofthe ester was obtained, confirmed by spectroscopy. Example 10: N-p-methylberιzoyl-1-arninobutyric acid- 1 -methyl- 1-pentyl ester N-p-methylbenzoyl-1 -aminobutyric acid- 1 -methyl- 1-pentyl ester The mixture of 2.0gr DL-p methylbenzoyl-3 amonobutyric acid (III), 1.6gr 2-hexanol, 30 ml toluene and 0.04gr H 2 SO4 (cone) was heated under reflux for ca 7 hr. The water formed in the reaction was separated by azeotropic distillation. The cooled reaction mixture was washed with 3X15ml water, 2X15ml bicarbonate 2% and dried over MgSO 4 . After distillation of solvent and alcohol 2.2gr ofthe ester was obtained, confirmed by spectorscopy. Example 11: DL-N-benzoyl-3 -aminobutyric acid 2-chloroethyl ester DL-N-benzoyl-3 -aminobutyric acid 2-chloroethyl ester To 1.68gr DL-N-benzoyl-3 -aminobutyric acid chloride, prepared in an analogous way as the acid chloride VII (Example 6), in 25ml DCE was added 2.5 gr 2-chloroethanol in 5ml DCE during 10 minutes, at 19-20°C. The mixture was heated at 65-67°C for ca 7hr. After distillation ofthe solvent and alcohol, 20ml of DCE was added, and washed with 2% bicarbonate. Evaporation ofthe solvent yield 1.4gr product, confirmed by spectroscopy. Example 12 : N-benzenesulfonyl-3 -aminobutyric acid-1 methyl 2-methoxy ethyl ester. To 6.0 gr of β-Aminobutyric acid in 20 ml water, was added 5.4gr of NaOH dissolved in 26 ml water. 10.3 gr of benzensulfonyl chloride in 36 ml dichloroethane was added at r.t. during 15 minutes. The mixture was stirred 10 minutes at r.t. and heated at 68°C during 4 hr. The phases were separated, and the aqueous one, was acidified with HCl (cone) to pH 2.5. After the extraction with dichloroethane, n-benzenesulfonyl-3 -aminobutyric acid crystallized from the organic phase. 6.7gr m.p. 125-127.4°C to 7.7gr of n-benzenesulfonyl-3 -aminobutyric acid in 80 ml DCE, was added 7.5gr in small portions, keeping the mixture temperatured at 5°C. The mixture was allowed to warm to r.t. and stirred during 6 hr. Petrol ether 60-80 (400ml) was added, the chloride was filter and dried yielding 7.3gr ofthe acid chloride. The 2.0gr ofthe acid chloride in 30ml DCE was added l-methoxy-2-propanol dissolved in 5ml DCE at 10-15°C. The mixture was heated at 63-65°C during 6.5hr. The reaction was washed twice with 20 ml water and sodium bicarbonate 2% and dried over MgSO and Distillation ofthe solvent and excess alcohol yield 1.75% ofthe product. The structure was confirmed by MS and NMR spectroscopic methods. By proceeding as described above, using the suitable starting materials compounds 19,29,31,36 and 47 were prepared. Example 13 : N-2-methylaminobenzoyl-3-aminobutyric acid methyl ester. The mixture of 17.7grN-methylisatoic anhydride, 10.3gr β-Aminobutyric acid, 1.5gr triethylamine and 150ml Toluene, was refluxed during 7hr. The solids were removed by filtration and N-2-methylaminobenzoyl-3-aminobutyric acid crystallized from the filtrate. The compound was filtered and washed with water and toluene where 5.4gr were obtained. To 2.0gr of N-2-methylaminobenzoyl-3-aminobutyric acid in 19gr methanol, 2,3gr of thionyl chloride was added at r.t. The mixture was heated to 60°C during 6.5hr. After the distillation of methanol, 50ml Dichloroethane was added. The solution was washed twice with 25ml sodium bicarbonate 2%, 25ml water and dried over MgSO 4 . After the evaporation ofthe solvent, 1.8gr product was obtained. NMR and MS spectroscopic methods confirmed the structure.. Example 14: N-4-methoxy-benzoyl-3 -aminobutyric acid n-heptyl ester. To 9.2gr β-aminobutyric acid in 32ml water, was added 15.6gr of NaON in 40 ml water. 16.6gr of 4-methoxybenzoylchloride in 60 ml Dichloroethane (DCE) was added during 20 minutes at 15-20°C. The mixture was heated at 65°C during 7.5 hr. The phases were separated, and the aqueous one was acidified with HCl (cone) to pH 2-2.5. The compound precipitated. 18.7gr of n-4-methoxy-benzoyl-3 -aminobutyric acid was obtained m.p. 112-116 after recrystallization with DCE. The mixture of 2.0gr n-4-methoxy-benzoyl-3-aminobutyric acid, 1.6gr 1-heptanol, 30ml Toluene and 0.04gr H 2 SO 4 (conc) was heated under reflux for 7 hr. The water formed in the reaction was separated by a zeotropic distillation. The cooled reaction was washed twice with 25ml water. After the evaporation ofthe solvent, the excess alcohol was distilled at 90°C (0.4mm Hg) and 0.8gr product was obtained. NMR and MS spectroscopic methods confirmed the sturcture. Example 15 : N-benzoyl- -aminobutyric acid-cyclohexyl ester. The mixture of 2.0 gr n-benzoyl-3 -aminobutyric acid, 1.6gr cyclohexanol, 30ml toluene and 0.04gr H 2 SO (cone) was heated under reflux during 2 hr, the water formed in the reaction was separated by azeotropic distillation. The cooled solution was washed with water and twice with 30ml 2% sodium bicarbonate. After the evaporation ofthe solvent, and distillation ofthe excess alcohol at 50°C, o.4mmHg, 1.5% oily product, which soldified, was obtained, m.p. 60-63°C. The sturcture was confirmed by MS and NMR spectoroscopic methods. Example 16 : N-benzoyl-3 -aminobutyric acid-2 propenyl ester (compound 42) The mixture of lOgr n-benzoyl-3 -aminobutyric acid 4.8gr allylalcohol, 70ml toluene and 0.2gr H 2 SO 4 (cone) was heated under reflux during 7 hr. The water formed in the reaction was separated by azeotropic distillation. The solution was washed with water, 2% sodium bicarbonate and dried over MgSO After the distillation ofthe solvent 5.0% ofthe product was obtained. MS and NMR spectroscopic methods approved the sturcture. Compounds 12-18, 20-28, 30-35,37-46 and 48 were prepared by similar manners to those described in examples 13-16 using suitable starting materials. I. Activity against late blight in potato and tomato. For the following experiments we have used six weeks old potted potato plants (Solanum tuberosum cultivar Alpha) or 4-weeks old potted tomato plants (Lycopersicon esculentum cultivar Florida basket). Plants were sprayed with the test compound and two days later were challenge inoculatedd with the lated blight fungus Phvtophthora infestans. Inoculation was carried out as follows: 1. The fungus was grown on potato tuber slices at 15°C for 7 days. 2. Sporaganic produced on tuber slices were harvested into cold (4°C) distilled water and their concentration adjusted to 2.5-3X10 3 sporaganic/ml. 3. Sporangical suspension was sprayed to run off onto the treated plants. Untreated plants were also inoculated as controls. 4. Inoculated plants were placed in a dew chamber at 18°C for 20 hr and then transferred into a growth chamber at 20°C with 12 hr lighr photoperiod and 60-70% RH. 5. At 4-7 days post inoculation the intensity of disease developed was visually activated by assessing the percentage ofthe foliage area killed by the fungus. 6. Control efficacy achieved by the spray treatment was calculated relative to the disease intensity seen on the control plants. For example when % foliage area killed was 90% in the control plants and 10% in the treated plants, control efficancy was calculated as (1-10). 100=88.0% 90 Results are shown in Tables 1 and 2. Table l g h y tn phthora infc g * » " g in P otato aXϊd toma o Tnntrnl Efficacy % Potato Tomato Compounds 26.7.96 17.7.096 14.8.96 12.7.96 14.8/96 from 500 2000 5002000 2000_ (pp ). 500 2000 2000 (ppm (ppml (Ppm) (ppm) Example 1 49 79 57 77 72 82 97 90 Example 2 42 68 45 81 74 85 85 83 Example 6 - 75 50 88 76 79 67 Example 3 85 92 70 81 88 70 93 Example 4 23 42 56 75 77 85 90 Table 2. Activity of some BAB A derivatives against late blight caused by Phvtophthora infestans in potato. 3-8 days after inoculation. Dose : 2000 ppm Control efficacy % Compounds 3 days 4 days 6 days 8 days from Example 7 100 100 82 77 Example 8 100 92 87 50 Example 9 99 97 82 62 Example 10 100 100 97 87 Example 11 95 92 82 70 Experimental Late blight in potato caused by Phvtophthora infestans. additional examples Potato plants (cv. Alpha) were raised from tubers in 1 liter pots in the greenhouse. At 4 weeks after "sowing" when had 3-4 shoots with 10-12 leaves, plants were sprayed with test solutions onto their adaxial surfaces and incubated at 20°C growth cabinets. Two days after spray plants were inoculated with sporangial suspension (2000 sporangia ml) of P. infestans (A2 mating type, resistant to metalaxyl). Inoculated plants were placed in 100% relative humidity in the dark for 20 hours and then returned to a 20°C growth cabined for symptom production. Percentage leaf area covered with blight symptoms was visually assessed 6 days after inoculation. Control efficacy was calculated relative to the control inoculated plants. The results are shown in Table 3. Table 3. Activity of some additional BAB A derivatives against late blight caused bv Pytophtora infestans i n Potato. 6 davs after inoculation. Dose: 500 ppm CH 3 C(H)NHR 7 CH 2 C(O)-OR 3 Control efficacy (%) Compd. R 7 R 3 6d 12 4-CH3OC6ILCO (CH 2 ) 6 CH 3 89 13 6,5-(CH 6 ) 2 C 6 H 6 CO (CH 2 ) 6 CH 3 84 48 2-C 4 H 3 SCO (CH2)7CH3 82 14 2,6-F 2 C 6 HeCO (CH 2 ) 6 CH 3 79 15 4-C(CH6)6C 6 H4CO (CH 2 ) 6 CH 3 79 16 4-CH6C6H4SO 2 CH(CH 6 )(CH 2 ) 6 CH 3 79 50 4-ClC 6 H 5 SO 2 CH(CH 3 )(CH 2 ) 3 CH 3 77 18 4-CIC6H 4 CO CH(CH 3 )(CH 2 ) 3 CH 3 76 51 CeH 5 SO 2 (CH 2 ) 3 C6H5 76 49 2-C4H 3 SCO CH(CH 3 )(CH 2 ) 3 CH 3 75 20 4-CH6C6H4SO2 CH(CH 3 )CH 2 CH 3 75 52 2-CH 3 NHC 6 H4CO CH(CH 3 )(CH 2 ) 3 CH 3 74 22 δ-CHe ILCO (CH 2 ) S CH 3 70 PC17IL97/00423 18 Late blight in tomato caused by Phvtophthora infestans Tomato plants (cv.baby) were raised from seed in 0.2 liter pots in the greenhouse. At 3 weeks after sowing when had 6 leaves plants were sprayed with the test solution onto their adaxial surfaces. They were inoculated and further handled and assessed for disease development as described in Section 1 above. The results are shown in Table 4. Table 4. Activity of some BAB A derivatives against late blight caused by Pytophtora infestans in Tomato. 7 days after inoculation. Dose: 500 ppm CH 3 C(H)NHR 7 CH 2 C(O)-OR 3 Control efficacy % Compd. RT R 3 7d 35 ClC 6 H 5 SO 2 CH 2 CH 2 CH 3 81 36 4-CH 3 C 6 H4CO CH 2 CC1 3 81 37 4-CH 3 C 6 H4CO cyclohexyl 78 38 C 6 H 5 CO cyclohexyl 78 39 CβHsSO, cyclohexyl 75 52 2-CH 3 NHC 6 H4CO CH(CH 3 )(CH 2 ) 3 CH 3 75 II. Activity against powdery mildew in cereals For the following experiments we have used 10-days old potted wheat plants (Triticum asetivum cultivar Atir) and barley plants (Hhordeum vulgaris cultivar Amidon). Plants were sprayed with the test compounds and two days lated were inoculated with the powdery mildew fungal pathogens. Wheat was inoculated with Erysiphe granims tritici. Barley was inoculated with the powdery Erysiphe granims hordei. Inoculation was done by shaking infected donor plants harboring abundant conidia over the treated plants. Untreated plants were also inoculated as controls. Inoculated plants were placed in a growth chamber at 20-22C with Irhr photoperioed and 50-60% RH. At 9-10 days after inoculation disease intesity was visually assessed by estimating the percentage leaf area occupied by fungal colonies Control efficacy ofthe disease achieved by the sprayed test compound was calculated relative to the amount of disease seen in the control. For example when % foliage area occupied by fungal colonies was 90% treated plants, control efficacy was calculated as (1-10). 100=88.9% 90 Results are shown in Table 5 Table 5. Activity of some BAB A derivatives against powdery mildew caused by Erysiphe graminis in cereals. Control Efficacy % Compound from Barley 17.9.96 Wheat 7.8.96 ppm 500 2000 500 2000 Example 1 25 75 - - Example 6 62 75 - - Example 4 87 95 96 96 Example 5 82 85 76 92 Powdery mildew in wheat caused by Erysiphe graminis tritici, additional examples. Wheat plants (cv.Shafir) were raised from seed in the greenhouse, 30 plants per 0.2 liter pot. When the first leaf was fully developed plants were sprayed with the test solutions and placed in a 20°C growth cabinet. Two days after spraying plants were dusted with conidia of E. graminis tritict so that about 100 spores were settled on 1 cm 2 of leaf area (both surfaces). Inoculated plants were placed in a 20°C growth cabinet for 7 days until number of fungal colonies per plant were counted. Control efficacy was calculated relative to number of colonies developed on the control-inoculated untreated plants. The results are shown in Table 6. Table 6. Activity of some BAB A derivatives against powdery mildew caused by Erysiphe graminis in wheat . 7 days after inoculation. Dose: 500 ppm CH 3 C(H)NHR 7 CH 2 C(O)-OR 3 Control efficacy (%) Compd. R 7 R 3 7d 38 C 6 H 5 C0 Cyclohexyl 100 53 CeH 5 SO 2 3,5-(Cl) 2 C 6 H 3 100 50 4-C1C6H4SO2 CH(CH 3 )(CH 2 ) 3 CH 3 92 12 4-CH 3 OC 6 H,CO (CH 2 ) 6 CH 3 85 32 2-CH3CH.CO (CH 2 ) 6 CH 3 83 16 4-CH 3 C 6 H S0 2 CH(CH 3 )(CH 2 ) 3 CH 3 83 35 4-ClCJLSO 2 CH 2 CH 2 CH 3 81 41 CJ SO, CH 3 CH CH 2 77 42 C 6 H 5 C0 CH 2 CH=CH 2 77 43 4-0^0^00 CH(CH S )(CH 2 ) 4 CH 3 75 44 4-CH3CACO CH(CH 3 )(CH 2 ) 6 CH 3 74 15 4-C(CH 3 ) 3 C 6 H 4 CO (CH 2 ) 6 CH 3 74 45 3,4 diCH^J CO (CH 2 ) 6 CH 3 71 46 4-CH 3 CJLCO CH(CH 3 )(CH 2 ) 3 CH 3 69 54 3,4-(CH 3 ) 2 CeH 3 CO (CH 2 ) 7 CH 3 69 III. Downy mildew in cucumber and melon caused by Pseudoperonospora cubensis Cucumber plants (cv,Dlila) and melon plants (cv.Ein Dor) were raised from seeds in 0.2 liter pots in the greenhouse. At 3 weeks after sowing when had 3 true leaves they were inoculated with sporangial suspension (1000 sporangia/ml) of P.cubensis (resistant to metalaxyl) and placed in 100% relative humidity in the dark for 20hr. They were then place in a 20°C growth cabinet for 7 days and assessed for disease development. Percentage leaf area covered with disease symptoms was evaluated and control efficacy was calculated relative to control inoculated plants. The results are shown in Tables 7 and 8. Table 7. Activity of some BABA derivatives against downy mildew caused by Pseudoperonospora cubesis in melon. 7 days after inoculation. Dose: 500 ppm CH 3 C(H)NHR 7 CH 2 C(O)-OR 3 Control efficacy % /o Compd. R 7 R3 7 days 12 4-CH 3 OC 6 H4CO (CH 2 ) 6 CH 3 100 15 4-C(CH 3 ) 3 CeH4CO (CH 2 ) 6 CH 3 97 17 C 6 H 5 SO 2 (CH ) 3 CeH 5 87 18 4-ClCeH4CO CH(CH 3 )(CH 2 ) 3 CH 3 87 51 C 6 H 5 SO 2 (CH 2 ) 3 CόH 5 87 22 3-CH 3 CeH 4 CO (CH 2 ) 6 CH 3 83 19 C 6 H 5 SO 2 CH 2 CC1 3 83 25 3,4Cl 2 CeH 3 CO CH(CH 3 )(CH 2 ) 3 CH 3 80 32 2-CH 3 C 6 H4CO (CH 2 ) 6 CH 3 77 33 4-CH 3 CeH4SO 2 CH 2 CH 2 Br 75 27 3,5-(CH 3 ) 2 C 6 H 3 CO CH 2 CH 2 C1 73 23 3,5-(CH 3 ) 2 C6H 3 CO CH(CH 3 )(CH 2 ) 3 CH 3 73 34 4-CH 3 CeH4SO 2 (CH 2 ) 6 CH 3 70 29 CeHsCO CH 2 CC1 3 70 Table 8. Activity of some BABA derivatives against dony mildew caused by Pseudoperonospora cubesis in cucumber. 7 days after inoculation. Dose: 500 ppm CH 3 C(H)NHR 7 CH 2 C(O)-OR 3 Control efficacy (%) Compd. RT R 3 7d 52 2-CH 3 NHCeH4CO CH(CH 3 )(CH 2 ) 3 CH 3 97 40 ClCeHsSO, (CH 2 ) 6 CH 3 82 36 4-CH 3 C 6 H4CO CH 2 CC1 3 82 38 CeHjCO Cyclohexyl 80 35 ClC 6 H 5 SO 2 CH CH CH 3 77 37 4-CH 3 C 6 H4CO Cyclohexyl 75 39 CeHsSO, Cyclohexyl 70 IV. Downy mildew in grapes caused by Plasmoparaylticola Grape plants (cv. Superior) were raised from cuttings and when developed 5-6 expanded leaves they were sprayed with the test solutions on their abaxial (lower) leaf surfaces. Two days after spraying plants were inoculated with sporangial suspension of P.viticola (10 4 sporangia/ml) onto their lower leaf surface and placed in 100% relative humidity for 20hr. The plants were then placed in a growth cabinets 20°C for 10 days. Disease development was assessed according to the abaxial leaf surfaces area covered with fungal sporulation. Fungal sporulation was induced by placing the infected plants in 100% relative humidity in the dark for 48hr. The results are shown in Table 9. Table 9. Activity of some BABA derivatives against downy mildew caused by Peronospora viticola in Grapes. 10 days after inoculation- Dose: 500 ppm CH 3 C(H)NHR 7 CH 2 C(O)-OR 3 Control efficacy % /O Compd. RT R 3 lOd 16 4-CH 3 CeH4SO 2 CH(CH 3 )(CH 2 ) 3 CH 3 100 14 2,6-F 2 C 6 H 3 CO (CH 2 ) 6 CH 3 100 23 3,5-(CH 3 ) 2 CeH 3 CO CH(CH 3 )(CH 2 ) 3 CH 3 100 20 4-CH3C6H4SO2 CH(CH 3 )CH 2 CH 3 100 24 3,4Cl 2 CeH 3 CO (CH 2 ) 6 CH 3 100 25 3,4Cl 2 C 6 H 3 CO CH(CH 3 )(CH 2 ) 3 CH 3 100 26 4-CH 3 C 6 H 4 C0 (CH 2 ) 3 CβH5 99 15 4-C(CH 3 ) 3 C 6 H4CO (CH 2 ) 6 CH 3 97 27 3,5-(CH 3 ) 2 C6H 3 CO CH 2 CH 2 C1 97 17 C 6 H 5 S0 2 (CH 2 ) 3 CeH 5 97 51 C6H 5 SO 2 (CH 2 ) 3 CeH5 97 19 C 6 H 5 S0 2 CH 2 CC1 3 94 28 4-CH 3 OCeH4CO CH 2 CH 2 C1 91 29 CeHsCO CH 2 CC1 3 91 30 4-CIC6H4CO (CH 2 ) 6 CH 3 ) 91 18 4-ClC 6 H4CO CH(CH 3 )(CH 2 ) 3 CH 3 91 31 C6H 5 SO 2 CH(CH 3 )CH 2 OCH 3 82

Claims: WHAT IS CLAIMED: 1. A compound having the formula (I) Wherein: a) Ri and R 2 are independently hydrogen, Cι- 8 alkyl, phenyl, and phenyl C1-4 alkyl b) R 3 is Ci-23 straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyli halogenated alkyl, phenyl, or benzyl; alkyl phenyl; c) R 4 and 5 are independently hydrogen or Cι- 8 alkyl; d) R is hydrogen; Cι- 8 alkyl; C 2 - 8 alkanoyl; phenyl Cι- 4 alkyl, benzoyl wherein the phenyl moiety is optionally substituted by one or more halogen atoms or alkyl groups C 2 - 8 alkoxycarbonyl; CONHRs wherein Rs is hydrogen, Cι- 8 alkyl, phenyl, phenyl Cι- alkyl; phenyl C 2 - 4 alkyloxycarbonyl; e) R 7 is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; f) X is O or NH and salts thereof. 2. A compound according to claim 1, wherein R t and R 2 are independently hydrogen, R 3 is straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyli halogenated alkyl, phenyl, or benzyl; alkyl phenyl; R 4 and R5 are independently hydrogen or C 3 alkyl; Re is hydrogen: R is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; and X is oxygen or-NH. 3. A compound according to claim 1, wherein Ri, R 2 , Rs, and R are hydrogen: R 3 is Ci-23 straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyli halogenated alkyl, phenyl, or benzyl; alkyl phenyl, or benzyl: R 4 is methyl: and R 7 is benzenesulfonyl; or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; and X is oxygen or NH. 4. A compound according to claim 1, wherein the compound is D,L-N-benzensulfonyl-3- amino N-benzyl butyramide. 5. A compound according to claim 1, wherein the compound is D,L-N-benzensulfonyl-3- aminobutyranilide . 6. A compound according to claim 1, wherein the compound is D,L-N-p-chlorobenzoyl-3- aminobutyric acid-2-chloroethyl ester. 7. A compound according to claim 1, wherein the compound is D,L-N-p-methyl benzoyl-3- aminobutyric acid, n-octyl ester. 8. A compound according to claim 1, wherein the compound is N-p-methyl benzoyl-3- aminobutyric acid, sec. butyl ester. 9. A compound according to claim 1, wherein the compound is D,L-N-3,4,-dichlorobenzoyl- 3 -aminobutyric acid, n-octyl ester. 10. A compound according to claim 1, wherein the compound is DL-N-benzoyl-3 - aminobutyric acid-2-chloroethyl ester. 11. A compound according to claim 1, wherein the compound is N-p-methyl benzoyl-3- aminobutyric acid- 1 -methyl- 1-pentyl ester. 12. A compound according to claim 1, wherein the compound is DL-N-benzene sulfonyl-3- aminobutyric acid, n-octyl ester. 13. A compound according to claim 1, wherein the compound is N-benzene sulfonyl-3- aminobutyric acid, sec butyl ester. 14. A compound according to claim 1, wherein the compound is N-benzene sulfonyl-3- aminobutyric acid, 1 -methyl- 1 -butyl ester. 15. A compound according to claim 1, wherein the compound is D,L N-4-methoxybenzoyl-3- aminobutyric acid heptyl ester. 16. A compound according to claim 1, wherein the compound is D,L N-3, 5 -dimethylbezoyl-3 - aminobutyric acid heptyl ester. 17. A compound according to claim 1, wherein the compound is D,L N-2,6-difluorobenzoyl- 3 -aminobutyric acid heptyl ester. 18. A compound according to claim 1, wherein the compound is D,L N-4-tertbutylbenzoyl-3- aminobutyric acid heptyl ester. 19. A compound according to claim 1, wherein the compound is D,L N-4- methylbenzenesulfonyl-3-aminobutyric acid 1-methylpentyl ester. 20. A compound according to claim 1, wherein the compound is D,L N-benzenesulfonyl-3 - aminobutyric acid 3-phenylpropyl ester. 21. A compound according to claim 1, wherein the compound is D,L N-4-cholrobenzoyl-3- aminobutyric acid 1-methylpentyl ester. 22. A compound according to claim 1, wherein the compound is D,L N-benzenesulfonyl-3 - aminobutyric acid 2-(trichloromethyl)ethyl ester. 23. A compound according to claim 1, wherein the compound is D,L N-4- methylbenzenesulfonyl-3 -aminobutyric 1-methylpropyll ester. 24. A compound according to claim 1, wherein the compound is D,L N-3,4-dimethylbezoyl-3- aminobutyric acidl-methylbutyl ester. 25. A compound according to claim 1, wherein the compound is D,L N-3-methylbezoyl-3- aminobutyric acid heptyl ester. 26. A compound according to claim 1, wherein the compound is D,L N-3, 5 -dimethylbezoyl-3 - aminobutyric acid 1-methylpentyl ester. 27. A compound according to claim 1, wherein the compound is D,L N-2,6-dichlorobenzoyl- 3 -aminobutyric acid heptyl ester. 28. A compound according to claim 1, wherein the compound is D,L N-2,6-dichlorobenzoyl- 3 -aminobutyric acid 1-methylpentyl ester. 29. A compound according to claim 1, wherein the compound is D,L N-4-methylbenzoyl-3- aminobutyric acid 3-phenylpropyl ester. 30. A compound according to claim 1, wherein the compound is D,L N-3,5-dimethylbezoyl-3- aminobutyric acid 2-chloroethyl ester 31. A compound according to claim 1, wherein the compound is D,L N-4-methoxybenzoyl-3- aminobutyric acid 2-chloroethyl ester. 32. A compound according to claim 1, wherein the compound is D,L N-benzoyl-3 - aminobutyric acid 2-(trichloromethyl)ethyl ester. 33. A compound according to claim 1, wherein the compound is D,L N-benzoyl-3 - aminobutyric acid 2-(trichloromethyl)ethyl ester. 34. A compound according to claim 1, wherein the compound is D,L N-benzenesulfonyl-3 - aminobutyric acid l-methyl-2-methoxy ethyl ester. 35. A compound according to claim 1, wherein the compound is D,L N-2-methylbezoyl-3- aminobutyric acid heptyl ester. 36. A compound according to claim 1 , wherein the compound is D,L N-4- methylbenzenesulfonyl-3 -aminobutyric acid 2-bromoethyl ester. 37. A compound according to claim 1, wherein the compound is D,L N-4- methylbenzenesulfonyl-3 -aminobutyric acid heptyl ester. 38. A compound according to claim 1, wherein the compound is D,L N-4- chlorobenzenesulfonyl-3 -aminobutyric acid propyl ester. 39. A compound according to claim 1, wherein the compound is D,L N-4-methylbenzoyl-3- aminobutyric acid 2-(trichloromethyl)ethyl ester. 40. A compound according to claim 1, wherein the compound is D,L N-4-methylbenzoyl-3- aminobutyric acid cyclohexyl ester. 41. A compound according to claim 1, wherein the compound is D,L N-benzoyl-3 - aminobutyric acid cyclohexyl ester. 42. A compound according to claim 1, wherein the compound is D,L N-benzenesulfonyl-3 - aminobutyric acid cyclohexyl ester. 43. A compound according to claim 1, wherein the compound is D,L N-4- chlorobenzenesulfonyl-3 -aminobutyric acid heptyl ester. 44. A compound according to claim 1, wherein the compound is 44 D,L N-benzenesulfonyl-3 - aminobutyric acid propyl ester. 45. A compound according to claim 1, wherein the compound is D,L N-benzoyl-3 - aminobutyric acid 2-propenyl ester. 46. A compound according to claim 1, wherein the compound is D,L N-4-methylbenzoyl-3- aminobutyric acid 1-methylhexyl ester. 47. A compound according to claim 1, wherein the compound is D,L N-4-methylbenzoyl-3- aminobutyric acid 1-methyldecanyl ester. 48. A compound according to claim 1, wherein the compound is D,L N-3,4-dimethylbezoyl-3- aminobutyric acid heptyl ester. 49. A compound according to claim 1, wherein the compound is D,L N-4-methylbezoyl-3- aminobutyric acid 1-methylpentyl ester. 50. A compound according to claim 1, wherein the compound is D,L N-2- methylaminobenzoyl-3 -aminobutyric acid methyl ester. 51. A compound according to claim 1, wherein the compound is D,L N-4- chlorobenzensulfonyl-3-aminobutyric acid 1-methylpentyl ester. 52. A compound according to claim 1, wherein the compound is D,L N-benzensulphonyl-3- aminobutyric acid 3-phenylpropyl ester. 53. A compound according to claim 1, wherein the compound is D,L N-2- methylaminobenzoyl-3 -aminobutyric acid 1-methylpentyl ester. 54. A compound according to claim 1, wherein the compound is D,L N-benzensulfonyl -3- aminobutyric acid 3,5-dichlorophenyl. 55. A compound according to claim 1, wherein the compound is D,L N-4- methylaminobenzoyl-3-aminobutyric acid 1-methylpentyl ester. 56. A compound according to claim 1, wherein the compound is D,L N-3,4-dimethylbenzoyl- 3 -aminobutyric acid octyl ester. 57. A compound according to claim 1, wherein the compound is D,L N-2-thiophenecarbonyl- 3 -aminobutyric acid octyl ester. 58. A compound according to claim 1, wherein the compound is D,L N-2-thiophenecarbonyl- 3 -aminobutyric acid 1-methylpentyl ester. 59. A method for protecting a crop against fungal diseases comprising applying to the crop or its locus a composition containing an effective amount of a compound having the formula (I) wherein. a) Ri and R 2 are independently hydrogen, Cι- 8 alkyl, phenyl, and phenyl C1-4 alkyl; b) R 3 is C I - straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyli halogenated alkyl, phenyl, or benzyl; alkyl phenyl; c) 4 and R5 are independently hydrogen or Cι- 8 alkyl; d) R is hydrogen: Cι- 8 alkyl; C 2 - alkanoyl; phenyl C1-4 alkyl, benzoyl wherein the phenyl moiety is optionally substatuted by one or more halogen atoms or alkyl groups, C 2 - 8 alkoxycarbonyl; CONHRs wherein Rs is hydrogen, Cι- 8 alkyl, phenyl, phenyl C 1 - 4 alkyl; phenyl C 2 - 4 alkyloxycarbonyl; e) R 7 is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; f) X is O, or NH, and salts thereof. 60. A method according to claim 59 wherein Ri and R 2 are independently hydrogen, R 3 is d- 23 straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyli halogenated alkyl, phenyl, or benzyl; alkyl phenyl; optionally substituted by halogen; phenyl or benzyl, R4 and R5 are independently hydrogen or C 1-3 alkyl; Re is hydrogen; R 7 is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; and X is oxygen or-NH. 61. A method according to claim 59. wherein R 2 , R5, and Re are hydrogen: R 3 is Ci-23 straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyli halogenated alkyl, phenyl, or benzyl; R 4 is methyl; and R 7 is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; and X is oxygen or NH. 62. A method according to claim 59. wherein the compound is D,L-N-benzensulfonlyl-3- amino N-benzyl butyramide. 63. A method according to claim 59. wherein the compound is D,L-N-benzensulfonyl-3- aminobutyranilide . 64. A method according to claim 59. wherein the compound is D,L-N-p-chlorobenzoyl-3- aminobutyric acid-2-chloroethyl ester. 65. A method according to claim 59. wherein the compound is D,L-N-p-methyl benzoyl-3- aminobutyric acid n-octyl ester. 66. A method according to claim 59. wherein the compound is N-p-methylbenzoyl-3- aminobutyric acid sec butyl ester. 67. A method according to claim 59. wherein the compound is D,L-N-3,4,-dichlorobenzoyl-3- aminobutyric acid, n-octyl ester. 68. A method according to claim 59. wherein the compound is DL-N-benzoyl-3 -aminobutyric acid-2-chloroethyl ester. 69. A method according to claim 59. wherein the compound is N-p-methyl benzoyl-3- aminobutyric acid- 1 -methyl- 1-pentyl ester. 70. A method according to claim 59. wherein the compound is DL-N-benzene sulfonyl-3- aminobutyric acid, n-octyl. 71. A method according to claim 59. wherein the compound is N-benzene sulfonly-3- aminobutyric sec butyl ester. 72. A method according to claim 59. wherein the compound is N-benzene sulfonyl-3- aminobutyric acid, 1 -methyl- 1 -butyl ester. 73. A method according to claim 59 wherein the compound is D,L N-4-methoxybenzoyl-3- aminobutyric acid heptyl ester. 74. A method according to claim 59 wherein the compound is D,L N-3,5-dimethylbezoyl-3- aminobutyric acid heptyl ester. 75. A method according to claim 59 wherein the compound is D,L N-2,6-difluorobenzoyl-3- aminobutyric acid heptyl ester. 76. A method according to claim 59 wherein the compound is D,L N-4-tertbutylbenzoyl-3- aminobutyric acid heptyl ester. 77. A method according to claim 59 wherein the compound is D,L N-4- methylbenzenesulfonyl-3 -aminobutyric acid 1-methylpentyl ester. 78. A method according to claim 59 wherein the compound is D,L N-4- methylbenzenesulfonyl-3 -aminobutyric acid 1-methylpentyl ester. 79. A method according to claim 59 wherein the compound is D,L N-4-cholrobenzoyl-3- aminobutyric acid 1-methylpentyl ester. 80. A method according to claim 59 wherein the compound is D,L N-benzenesulfonyl-3 - aminobutyric acid 2-(trichloromethyl)ethyl ester. 81. A method according to claim 59 wherein the compound is D,L N-4- methylbenzenesulfonyl-3-aminobutyric 1-methylpropyll ester. 82. A method according to claim 59 wherein the compound is D,L N-3,4-dimethylbezoyl-3- aminobutyric acidl-methylbutyl ester. 83. A method according to claim 59 wherein the compound is D,L N-3-methylbezoyl-3- aminobutyric acid heptyl ester. 84. A method according to claim 59 wherein the compound is D,L N-3,5-dimethylbezoyl-3- aminobutyric acid 1-methylpentyl ester. 85. A method according to claim 59 wherein the compound is D,L N-2,6-dichlorobenzoyl-3- aminobutyric acid heptyl ester. 86. A method according to claim 59 wherein the compound is D,L N-2,6-dichlorobenzoyl-3- aminobutyric acid 1-methylpentyl ester. 87. A method according to claim 59 wherein the compound is D,L N-4-methylbenzoyl-3- aminobutyric acid 3-phenylpropyl ester. 88. A method according to claim 59 wherein the compound is D,L N-3,5-dimethylbezoyl-3- aminobutyric acid 2-chloroethyl ester. 89. A method according to claim 59 wherein the compound is D,L N-4-methoxybenzoyl-3- aminobutyric acid 2-chloroethyl ester. 90. A method according to claim 59 wherein the compound is D,L N-benzoyl-3 -aminobutyric acid 2-(trichloromethyl)ethyl ester. 91. A method according to claim 59 wherein the compound is D,L N-4-cholrobenzoyl-3- aminobutyric acid heptyl ester. 92. A method according to claim 59 wherein the compound is D,L N-benzenesulfonyl-3 - aminobutyric acid l-methyl-2-methoxyethyl ester. 93. A method according to claim 59 wherein the compound is D,L N-2-methylbezoyl-3- aminobutyric acid heptyl ester. 94. A method according to claim 59 wherein the compound is D,L N-4- methylbenzenesulfonyl-3 -aminobutyric acid 2-bromoethyl ester. 95. A method according to claim 59 wherein the compound is D,L N-4- methylbenzenesulfonyl-3 -aminobutyric acid heptyl ester. 96. A method according to claim 59 wherein the compound is D,L N-4- chlorobenzenesulfonyl- -aminobutyric acid propyl ester. 97. A method according to claim 59 wherein the compound is D,L N-4-methylbenzoyl-3- aminobutyric acid 2-(trichloromethyl)ethyl ester. 98. A method according to claim 59 wherein the compound is D,L N-4-methylbenzoyl-3- aminobutyric acid cyclohexyl ester. 99. A method according to claim 59 wherein the compound is D,L N-benzoyl-3 -aminobutyric acid cyclohexyl ester. 100. A method according to claim 59 wherein the compound is D,L N-beιιzenesulfbnyl-3- aminobutyric acid cyclohexyl ester. 101. A method according to claim 59 wherein the compound is D,L N-4- chlorobenzenesulfonyl-3 -aminobutyric acid heptyl ester. 102. A method according to claim 59 wherein the compound is D,L N-benzenesulfonyl-3 - aminobutyric acid propyl ester. 103. A method according to claim 59 wherein the compound is D,L N-benzoyl-3 -aminobutyric acid 2-propenyl ester. 104. A method according to claim 59 wherein the compound is D,L N-4-methylbenzoyl-3- aminobutyric acid 1-methylhexyl ester. 105. A method according to claim 59 wherein the compound is D,L N-4-methylbenzoyl-3- aminobutyric acid 1-methyldecanyl ester. 106. A method according to claim 59 wherein the compound is D,L N-3,4-dimethylbezoyl-3- aminobutyric acid heptyl ester. 107. A method according to claim 59 wherein the compound is D,L N-4-methylbezoyl-3- aminobutyric acid 1-methylpentyl ester. 108. A method according to claim 59 wherein the compound is D,L N-2-methylaminobenzoyl- 3 -aminobutyric acid methyl ester. 109. A method according to claim 59, wherein the compound is D,L N-4- chlorobenzensulfonyl-3-aminobutyric acid 1-methylpentyl ester. 110. A method according to claim 59, wherein the compound is D,L N-benzensulfonyl-3- aminobutyric acid 3-phenylpropyl ester. 111. A method according to claim 59, wherein the compound is D,L N-2-methylaminobenzoyl- 3 -aminobutyric acid 1-methylpentyl ester. 112. A method according to claim 59, wherein the compound is D,L N-benzensulphonyl -3- aminobutyric acid 3,5-dichlorophenyl. 113. A method according to claim 59, wherein the compound is D,L N-4-methylaminobenzoyl- 3 -aminobutyric acid 1-methylpentyl ester. 114. A method according to claim 59, wherein the compound is D,L N-3,4-dimethylbenzoyl-3- aminobutyric acid octyl ester. 115. A method according to claim 59, wherein the compound is D,L N-2-thiophenecarbonyl-3- aminobutyric acid octyl ester. 116. A method according to claim 59, wherein the compound is D,L N-2-thiophenecarbonyl-3- aminobutyric acid 1-methylpentyl ester. 117. A method according to claim 59 wherein the crop is selected from the group consisting of potatoes, tomatoes, grapes cereals, melons and cucumber. 118. A method according to any claim 59 tol 17 wherein the compound is applied to the leaves or stems ofthe plant. 119. A method according to any claim 59 tol 17 wherein the compound is applied to the roots ofthe plant. 120. A method according to any claim 59 to 117 wherein the compound is applied to the soil. 121. A method according to any claim 59 to 117 wherein the compound is applied to the seeds, tubers, or bulbs ofthe plant. 122. A method according to any claim 59 to 117 wherein the compound is applied pre- emergence. 123. A method according to any claim 59 to 117 wherein the compound is applied post- emergence. 124. A method according to any claim 59 to 117 wherein the compound is applied to the crop at a dosage rated of from 0.1 to 5 kg ha. 125. A method according to any claim 59 to 117 wherein the compound is applied to the crop at a dosage rate of 0.2 to 2 kg ha. 126. A method of protecting tomatoes or potatoes against Early Blight or Late Blight comprising of applying to the tomato or potato plant or its locus an effective amount of the compound having the formula (I) Wherein: a) Ri and R 2 are independently hydrogen, Cι- 8 alkyl, phenyl, and phenyl Cι- 4 alkyl; b) R 3 is Ci-a straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyli halogenated alkyl, phenyl, or benzyl; alkyl phenyl; c) R» and R5 are independently hydrogen or d- 8 alkyl; d) Re. is hydrogen; Cι- 8 alkyl; C 2 - 8 alkanoyl; phenyl C 1 - 4 , alkyl, benzoyl wherein the phenyl moiety is optionally substatuted by one or more halogen atoms or alkyl groups, C 2 - 8 alkoxycarbonyl; CONHRs wherein Rs is hydrogen, Ci-g alkyl, phenyl, phenyl C1-4 alkyl; phenyl C 2 - alkyloxycarbonyl; e) R 7 is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; f) X is O, or NH, and salts thereof. 127. A method according to claim 126, wherein Rt and R 2 are independently hydrogen, R 3 is Ci- 2 3 straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyli halogenated alkyl, phenyl, or benzyl alkyl phenyl; R 4 and R5 are independently hydrogen or Cl- 3 alkyl; R is hydrogen; R 7 is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; and X is oxygen or-NH. 128. A method according to claim 126, wherein Ri and R 2 ,R 5 , and Re are hydrogen: R 3 is Ci-23 straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyli halogenated alkyl, phenyl, or benzyl; alkyl phenyl; R 4 is methyl; and R is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; and X is oxygen or-NH. 129. A method according to claim 126 wherein the compound is D,L-N-benzensulfonyl-3- amino N-benzyl butyramide. 130. A method according to claim 126 wherein the compound is D,L-N-benzensulfonyl-3- aminobutyranilide. 131. A method according to claim 126 wherein the compound is D,L-N-p-methyl benzoyl-3- aminobutyric acid, n-octyl ester. 132. A method according to claim 126 wherein the compound is D,L-N-p-methyl benzoyl-3- aminogutyric acid, n-octyl ester. 133. A method according to claim 126 wherein the compound is D,L-N-p-methyl benzoyl-3- aminogutyric acid, sec.butyl ester. 134. A method according to claim 126 wherein the compound is D,L-N-3,4,-dichlorobenzoyl- 3 -aminobutyric acid, n-octyl ester. 135. A method according to claim 126 wherein the compound is D,L-N-benzoyl-3- aminobutyric acid-2-chlroethyl ester. 136. A method according to claim 126 wherein the compound is N-p-methyl benzoyl-3- aminobutyric acid- 1 -methyl- 1-pentyl ester. 137. A method according to claim 126 wherein the compound is D,L-N-benzene sulfonyl-3- aminobutyric acid, n-octyl ester. 138. A method according to claim 126 wherein the compound is N-benzene sulfonyl-3- aminobutyric acid, sec butyl ester. 139. A method according to claim 126 wherein the compound is N-benzene sulfonyl-3- aminobutyric acid, 1-methyl-l-l -butyl ester. 140. A method according to claim 126 wherein the compound is D,L N-4-methoxybenzoyl-3- aminobutyric acid heptyl ester. 141. A method according to claim 126 wherein the compound is D,L N-3,5-dimethylbezoyl-3- aminobutyric acid heptyl ester. 142. A method according to claim 126 wherein the compound is D,L N-2,6-difluorobenzoyl-3- aminobutyric acid heptyl ester. 143. A method according to claim 126 wherein the compound is D,L N-4-tertbutylbenzoyl-3- aminobutyric acid heptyl ester. 144. A method according to claim 126 wherein the compound is D,L N-4- methylbenzenesulfonyl-3 -aminobutyric acid 1-methylpentyl ester. 145. A method according to claim 126 wherein the compound is D,L N-benzenesulfonyl-3 - aminobutyric acid 3-phenylpropyl ester. 146. A method according to claim 126 wherein the compound is D,L N-4-cholrobenzoyl-3- aminobutyric acid 1-methylpentyl ester. 147. A method according to claim 126 wherein the compound is D,L N-benzenesulfonyl-3 - aminobutyric acid 2-(trichloromethyl)ethyl ester. 148. A method according to claim 126 wherein the compound is D,L N-4- methylbenzenesulfonyl-3 -aminobutyric 1-methylpropyll ester. 149. A method according to claim 126 wherein the compound is D,L N-3,4-dimethylbezoyl-3- aminobutyric acidl-methylbutyl ester. 150. A method according to claim 126 wherein the compound is D,L N-3-methylbezoyl-3- aminobutyric acid heptyl ester. 151. A method according to claim 126 wherein the compound is D,L N-4- chlorobenzenesulfonyl-3 -aminobutyric acid propyl ester. 152. A method according to claim 126 wherein the compound is D,L N-4-methylbenzoyl-3- aminobutyric acid 2-(trichloromethyl)ethyl ester. 153. A method according to claim 126 wherein the compound is D,L N-4-methylbenzoyl-3- aminobutyric acid cyclohexyl ester. 154. A method according to claim 126 wherein the compound is D,L N-benzoyl-3 - aminobutyric acid cyclohexyl ester. 155. A method according to claim 126 wherein the compound is D,L N-benzenesulfonyl-3 - aminobutyric acid cyclohexyl ester. 156. A method according to claim 126 wherein the compound is D,L N-2-thiophenecarbonyl- 3 -aminobutyric acid octyl ester. 157. A method according to claim 126 wherein the compound is D,L N-2-thiophenecarbonyl- 3 -aminobutyric acid 1-methylpentyl ester. 158. A method according to claim 126 wherein the compound is D,L N-2- methylaminobenzoyl-3 -aminobutyric acid 1-methylpentyl ester. 159. A method according to claim 126 wherein the compound is D,L N-benzenesulfonyl-3 - aminobutyric acid 3-phenylpropyl ester. 160. A method according to claim 126 wherein the compound is D,L N-4- chlorobenzenesulfonyl-3-aminobutyric acid 1-methylpentyl ester. 161. A method according to any of Claims 126-160 wherein the compound is applied to the leaves or stems ofthe plant. 162. A method according to any of Claims 126-160 wherein the compound is applied to the roots ofthe plant. 163. A method according to any of Claims 126-160wherein the compound is applied to the soil. 164. A method according to any of Claims 126-160 wherein the compound is applied to the seeds. 165. A method according to any of Claims 126-160 wherein the compound is applied post- emergence. 166. A method according to any of Claims 126-160 wherein the compound is applied pre- emergence. 167. A method according to any claim 126-160 wherein the compound is applied to the crop at a dosage rated of from 0.1 to 5 kg/ha. 168. A method according to any claim 126-160 wherein the compound is applied to the crop at a dosage rate of 0.2 to 2 kg/ha. 169. A method for protecting cereals against powdery mildew, by applying to cereal plant or its locus a composition containing an effective amount of a compound having the formula (I) wherein: a) Ri and R 2 are independently hydrogen, Cι- 8 alkyl, phenyl, and phenyl C 1 -4 alkyl b) R 3 is Cι- 3 straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyl halogenated alkyl, phenyl, or benzyl; alkyl phenyl; c) R4 and R 5 are independently hydrogen or Cι- 8 alkyl; d) Re is hydrogen; Cι- 8 alkyl; C 2 - 8 alkanoyl; phenyl C1-4 alkyl, benzoyol wherein the phenyl moiety is optionally substituted by one or more halogen atoms or alkyl groups C - 8 alkoxycarbonyl; CONHRs wherein Rg is hydrogen, Cι- 8 alkyl, phenyl, phenyl C 1 -4 alkyl; phenyl C - alkyloxycarbonyl; e) R 7 is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; f) X is O or NH and salts thereof; and the crop is selected from tomatoes, potatoes and cereals. 170. A method according to claim 169, wherein Ri and R 2 are independently hydrogen, R 3 is Cι- 23 straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyli halogenated alkyl, phenyl, or benzyl; alkyl phenyl; R4 and R5 are independently hydrogen or Cι- 3 alkyl; R is hydrogen: R 7 is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; and X is oxygen or-NH. 171. A method according to claim 169, wherein Ri, R 2 , R5, and Re are hydrogen: R 3 is C ^ straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyli halogenated alkyl, phenyl, or benzyl; alkyl phenyl, or benzyl: R4 is methyl: and R 7 is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; and X is oxygen or NH. 172. A method according to claim 169. wherein the compound is D,L-N-benzensulfonyl-3- amino N-benzyl butyramide. 173. A method according to claim 169. wherein the compound is D,L-N-benzensulfonyl-3- aminobutyranilide . 174. A method according to claim 169. wherein the compound is D,L-N-p-chlorobenzoyl-3- aminobutyric acid-2-chloroethyl ester. 175. A method according to claim 169. wherein the compound is D,L-N-p-methyl benzoyl-3- aminobutyric acid, n-octyl ester. 176. A method according to claim 169. wherein the compound is N-p-methyl benzoyl-3- aminobutyric acid, sec. butyl ester. 177. A method according to claim 169. wherein the compound is D,L-N-3,4,-dichlorobenzoyl- 3 -aminobutyric acid, n-octyl ester. 178. A method according to claim 169. wherein the compound is DL-N-benzoyl-3 - aminobutyric acid-2-chloroethyl ester. 179. A method according to claim 169. wherein the compound is N-p-methyl benzoyl-3- aminobutyric acid- 1 -methyl- 1-pentyl ester. 180. A method according to claim 169. wherein the compound is DL-N-benzene sulfonyl-3- aminobutyric acid, n-octyl ester. 181. A method according to claim 169. wherein the compound is N-benzene sulfonyl-3- aminobutyric acid, sec butyl ester. 182. A method according to claim 169. wherein the compound is N-benzene sulfonyl-3- aminobutyric acid, 1 -methyl- 1 -butyl ester. 183. A method according to claim 169. wherein the compound is D,L N-4-methoxybenzoyl-3- aminobutyric acid heptyl ester. 184. A method according to claim 169. wherein the compound is D,L N-3,5-dimethylbezoyl-3- aminobutyric acid heptyl ester. 185. A method according to claim 169. wherein the compound is D,L N-4-tertbutylbenzoyl-3- aminobutyric acid heptyl ester. 186. A method according to claim 169. wherein the compound is D,L N-4- methylbenzenesulfonyl-3 -aminobutyric acid 1-methylpentyl ester. 187. A method according to claim 169. wherein the compound is D,L N-2-methylbezoyl-3- aminobutyric acid heptyl ester. 188. A method according to claim 169. wherein the compound is D,L N-4- chlorobenzenesulfonyl-3 -aminobutyric acid propyl ester. 189. A method according to claim 169. wherein the compound is D,L N-benzoyl-3- aminobutyric acid cyclohexyl ester. 190. A method according to claim 169. wherein the compound is D,L N-benzenesulfonyl-3 - aminobutyric acid propyl ester. 191. . A method according to claim 169. wherein the compound is D,L N-benzoyl-3- aminobutyric acid 2-propenyl ester. 192. . A method according to claim 169. wherein the compound is D,L N-4-methylbenzoyl-3- aminobutyric acid 1-methylhexyl ester. 193. . A method according to claim 169. wherein the compound is D,L N-4-methylbenzoyl-3- aminobutyric acid 1-methyldecanyl ester. 194. . A method according to claim 169. wherein the compound is D,L N-3,4-dimethylbezoyl- 3 -aminobutyric acid heptyl ester. 195. . A method according to claim 169. wherein the compound is D,L N-2- methylaminobenzoyl-3-aminobutyric acid methyl ester. 196. A method according to claim 169. wherein the compound is D,L N-4-methylbezoyl-3- aminobutyric acid 1-methylpentyl ester. 197. A method according to claim 169. wherein the compound is D,L N-4- chlorobenzenesulphonyl-3 -aminobutyric acid 1-methylpentyl ester 198. A method according to claim 169. wherein the compound is D,L N-2- methylaminobenzoyl-3 -amino butyric acid methyl ester 199. A method according to claim 169. wherein the compound is D,LN-3,4-dimethylbenzoyl- 3 -amino butyric acid octyl ester 200. A method according to claim 169. wherein the compound is D,L N-benzensulphonyl-3- aminobutyric acid 3,5-dichlorophenyl ester 201. A method according to any claim 169 to200 wherein the compound is applied to the leaves or stems ofthe plant. 202. A method according to any claim 169-200 wherein the compound is applied to the roots ofthe plant. 203. A method according to any claim 169 to 200 wherein the compound is applied to the soil. 204. A method according to any claim 169 to 200 wherein the compound is applied to the seeds, tubers, or bulbs ofthe plant. 205. A method according to any claim 169 to 200 wherein the compound is applied pre- emergence. 206. A method according to any claim 169 to 200 wherein the compound is applied post- emergence. 207. A method according to any claim 169 to 200 wherein the compound is applied to the crop at a dosage rated of from 0.1 to 5 kg/ha. 208. A method for protecting cucumber against downy mildew, by applying to cucumber plant or its locus a composition containing an effective amount of a compound having the formula (I) wherein: a) Ri and R 2 are independently hydrogen, Cι- 8 alkyl, phenyl, and phenyl C1-4 alkyl b) R 3 is Cι-73 straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyl halogenated alkyl, phenyl, or benzyl; alkyl phenyl; c) R4 and R5 are independently hydrogen or Cι- 8 alkyl; d) Re is hydrogen; Cι- 8 alkyl; C 2 - alkanoyl; phenyl C 1 -4 alkyl, benzoyol wherein the phenyl moiety is optionally substituted by one or more halogen atoms or alkyl groups C 2 -8 alkoxycarbonyl; CONHRs wherein Rs is hydrogen, Ci-g alkyl, phenyl, phenyl C1-4 alkyl; phenyl C 2 - 4 alkyloxycarbonyl; e) R 7 is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; f) X is O or NH and salts thereof; and the crop is selected from tomatoes, potatoes and cereals. 209. A method according to claim 208, wherein Ri and R 2 are independently hydrogen, R 3 is Ci-23 straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyli halogenated alkyl, phenyl, or benzyl alkyl phenyl; R4 and R 5 are independently hydrogen or Cl- 3 alkyl; R is hydrogen; R 7 is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; and X is oxygen or-NH. 210. A method according to claim 208, wherem Ri and R_,R5, and Re are hydrogen: R 3 is Ci- 23 straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyli halogenated alkyl, phenyl, or benzyl; alkyl phenyl; R4 is methyl; and R is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; and X is oxygen or-NH. 211. A method according to claim 208, wherein the compound is D,L N-4- chlorobenzenesulfonyl-3 -aminobutyric acid propyl ester. 212. A method according to claim 208, wherein the compound is D,L N-4-methylbenzoyl-3- aminobutyric acid 2-(trichloromethyl)ethyl ester. 213. A method according to claim 208, wherein the compound is D,L N-4-methylbenzoyl-3- aminobutyric acid cyclohexyl ester. 214. . A method according to claim 208, wherein the compound is D,L N-benzoyl-3- aminobutyric acid cyclohexyl ester. 215. . A method according to claim 208, wherein the compound is D,L N-benzenesulfonyl-3 - aminobutyric acid cyclohexyl ester. 216. A method according to claim 208, wherein the compound is D,L N-4- chlorobenzenesulfonyl-3 -aminobutyric acid heptyl ester. 217. A method according to claim 208, wherein the compound is D,L N-2- methylaminobenzoyl-3-amino butyric acid 1-methylpentyl ester 218. A method according to any claim 208 to 217 wherein the compound is applied to the leaves or stems ofthe plant. 219. A method according to any claim 208 to217 wherein the compound is applied to the roots ofthe plant. 220. A method according to any claim 208 to 217 wherein the compound is applied to the soil. 221. A method according to any claim 208 to 217 wherein the compound is applied to the seeds, tubers, or bulbs ofthe plant. 222. A method according to any claim 208 to 217 wherein the compound is applied pre- emergence. 223. A method according to any claim 208 to 217 wherein the compound is applied post- emergence. 224. A method according to any claim 208 to 217 wherein the compound is applied to the crop at a dosage rated of from 0.1 to 5 kg ha. 225. A method according to any claim 208 to 217 wherein the compound is applied to the crop at a dosage rate of 0.2 to 2 kg/ha. 226. A method for protecting grapes against downy mildew, by applying to grape plant or its locus a composition containing an effective amount of a compound having the formula (I) wherein: a) Ri and R 2 are independently hydrogen, Cι- 8 alkyl, phenyl, and phenyl Cι- 4 alkyl b) R 3 is Cι- 23 straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyl halogenated alkyl, phenyl, or benzyl; alkyl phenyl; c) t and R 5 are independently hydrogen or Cι- 8 alkyl; d) Re is hydrogen; Cι- 8 alkyl; C 2 - 8 alkanoyl; phenyl C1-4 alkyl, benzoyol wherein the phenyl moiety is optionally substituted by one or more halogen atoms or alkyl groups C 2 - 8 alkoxycarbonyl; CONHRs wherein Rg is hydrogen, Cι- 8 alkyl, phenyl, phenyl C1- 4 alkyl; phenyl C 2 - 4 alkyloxycarbonyl; e) R 7 is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; f) X is O or NH and salts thereof. 227. A method according to claim 226, wherein Ri and R 2 are independently hydrogen, R 3 is Ci-23 straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyli halogenated alkyl, phenyl, or benzyl alkyl phenyl; R4 and R 5 are independently hydrogen or Cl- 3 alkyl; R is hydrogen; R is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; and X is oxygen or-NH. 228. A method according to claim 226, wherein R \ and R 2 ,R5, and Re are hydrogen: R 3 is d- 23 straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyli halogenated alkyl, phenyl, or benzyl; alkyl phenyl; R4 is methyl; and R 7 is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; and X is oxygen or-NH. 229. A method according to claim 226, wherein the compound is D,L N-2,6-difluorobenzoyl- 3 -aminobutyric acid heptyl ester. 230. A method according to claim 226, wherein the compound is D,L N-4-tertbutylbenzoyl-3- aminobutyric acid heptyl ester. 231. A method according to claim 226, wherein the compound is D,L N-4- methylbenzenesulfonyl-3-aminobutyric acid 1-methylpentyl ester. 232. A method according to claim 226, wherein the compound is D,L N-benzenesulfonyl-3 - aminobutyric acid 3-phenylpropyl ester. 233. A method according to claim 226, wherein the compound is D,L N-4-cholrobenzoyl-3- aminobutyric acid 1-methylpentyl ester. 234. A method according to claim 226, wherein the compound is D,L N-benzenesulfonyl-3 - aminobutyric acid 2-(trichloromethyl)ethyl ester. 235. A method according to claim 226, wherein the compound is D,L N-4- methylbenzenesulfonyl-3-aminobutyric 1-methylpropyll ester. 236. A method according to claim 226, wherein the compound is D,L N-3, 5 -dimethylbezoyl-3 - aminobutyric acid 1-methylpentyl ester. 237. A method according to claim 226, wherein the compound is D,L N-2,6-dichlorobenzoyl- 3 -aminobutyric acid heptyl ester. 238. A method according to claim 226, wherein the compound is D,L N-2,6-dichlorobenzoyl- 3 -aminobutyric acid 1-methylpentyl ester. 239. A method according to claim 226, wherein the compound is D,L N-4-methylbenzoyl-3- aminobutyric acid 3-phenylpropyl ester. 240. A method according to claim 226, wherein the compound is D,L N-3,5-dimethylbezoyl-3- aminobutyric acid 2-chloroethyl ester. 241. A method according to claim 226, wherein the compound is D,L N-4-methoxybenzoyl-3- aminobutyric acid 2-chloroethyl ester. 242. A method according to claim 226, wherein the compound is D,L N-benzoyl-3- aminobutyric acid 2-(trichloromethyl)ethyl ester. 243. A method according to claim 226, wherein the compound is D,L N-4-cholrobenzoyl-3- aminobutyric acid heptyl ester. 244. A method according to claim 226, wherein the compound is D,L N-benzenesulfonyl-3 - aminobutyric acid l-methyl-2-methoxyethyl ester. 245. A method according to claim 226, wherein the compound is D,L N-benzenesulfonyl-3 - amnio butyric acid 3-phenylpropyl ester. 246. A method according to any claim 226 to245 wherein the compound is applied to the leaves or stems ofthe plant. 247. A method according to any claim 226 to245 wherein the compound is applied to the roots ofthe plant. 248. A method according to any claim 226 to 245 wherein the compound is applied to the soil. 249. A method according to any claim 226 to 245 wherein the compound is applied to the seeds, tubers, or bulbs ofthe plant. 250. A method according to any claim 226 to 245 wherein the compound is applied pre- emergence. 251. A method according to any claim 226 to 245 wherein the compound is applied post- emergence. 252. A method according to any claim 226 to 245 wherein the compound is applied to the crop at a dosage rated of from 0.1 to 5 kg/ha. 253. A method according to any claim 226 to 245 wherein the compound is applied to the crop at a dosage rate of 0.2 to 2 kg/ha. 254. A method for protecting melons against downy mildew, by applying to melon plant or its locus a composition containing an effective amount of a compound having the formula (I) wherein: a) Ri and R 2 are independently hydrogen, d- 8 alkyl, phenyl, and phenyl d- alkyl b) R 3 is Cι-:23 straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyl halogenated alkyl, phenyl, or benzyl; alkyl phenyl; c) R4 and R5 are independently hydrogen or Cι- 8 alkyl; d) e is hydrogen; Cι- 8 alkyl; C 2 - 8 alkanoyl; phenyl C1-4 alkyl, benzoyol wherein the phenyl moiety is optionally substituted by one or more halogen atoms or alkyl groups C 2 - 8 alkoxycarbonyl; CONHRs wherein Rg is hydrogen, Cι- 8 alkyl, phenyl, phenyl Cι- 4 alkyl; phenyl C 2 - 4 alkyloxycarbonyl; e) R 7 is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; f) X is O or NH and salts thereof; 255. A method according to claim 234, wherein Ri and R 2 are independently hydrogen; R 3 is d-2 3 straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyli halogenated alkyl, phenyl, or benzyl alkyl phenyl; R4 and R5 are independently hydrogen or Cl- 3 alkyl; R« is hydrogen; R 7 is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; and X is oxygen or-NH. 256. A method according to claim 234, wherein Ri and R ,R5, and Re are hydrogen: R 3 is d- 23 straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyli; halogenated alkyl, phenyl, or benzyl; alkyl phenyl; R4 is methyl; and R 7 is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl; and X is oxygen or-NH. 257. A method according to claim 234, wherein the compound is D,L N-4-methoxybenzoyl-3- aminobutyric acid heptyl ester. 258. A method according to claim 234, wherein the compound is D,L N-4-tertbutylbenzoyl-3- aminobutyric acid heptyl ester. 259. A method according to claim 234, wherein the compound is D,L N-benzenesulfonyl-3 - aminobutyric acid 3-phenylpropyl ester. 260. A method according to claim 234, wherein the compound is D,L N-4-cholrobenzoyl-3- aminobutyric acid 1-methylpentyl ester. 261. A method according to claim 234, wherein the compound is D,L N-benzenesulfonyl-3 - aminobutyric acid 2-(trichloromethyl)ethyl ester. 262. A method according to claim 234, wherein the compound is D,L N-3-methylbezoyl-3- aminobutyric acid heptyl ester. 263. A method according to claim 234, wherein the compound is D,L N-3, 5 -dimethylbezoyl-3 - aminobutyric acid 1-methylpentyl ester. 264. A method according to claim 234, wherein the compound is D,L N-2,6-dichlorobenzoyl- 3 -aminobutyric acid 1-methylpentyl ester. 265. A method according to claim 234, wherein the compound is D,L N-3, 5 -dimethylbezoyl-3 - aminobutyric acid 2-chloroethyl ester. 266. A method according to claim 234, wherein the compound is D,L N-benzoyl-3- aminobutyric acid 2-(trichloromethyl)ethyl ester. 267. A method according to claim 234, wherein the compound is D,L N-2-methylbezoyl-3- aminobutyric acid heptyl ester. 268. A method according to claim 234, wherein the compound is D,L N-4- methylbenzenesulfonyl-3 -aminobutyric acid 2-bromoethyl ester. 269. A method according to claim 234, wherein the compound is D,L N-4- methylbenzenesulfonyl-3 -aminobutyric acid heptyl ester. 270. A method according to claim 234, wherein the compound is D,L N-benzenesulphonyl-3- aminobutyric acid 3-phenylpropyl ester 271. A method according to any claim 254 to270 wherein the compound is applied to the leaves or stems ofthe plant. 272. A method according to any claim 254 to270 wherein the compound is applied to the roots ofthe plant. 273. A method according to any claim 254 to 270 wherein the compound is applied to the soil. 274. A method according to any claim 254 to 270 wherein the compound is applied to the seeds, tubers, or bulbs ofthe plant. 275. A method according to any claim 254 to 270 wherein the compound is applied pre- emergence. 276. A method according to any claim 254 to 270 wherein the compound is applied post- 277. A method according to any claim 254 to 270 wherein the compound is applied to the crop at a dosage rated of from 0.1 to 5 kg/ha. 278 A method according to any claims 254 to 270 wherein the compound is applied to the crop at a dosage rate of 0.2 to 2 kg/ha.

Inventors: COHEN YIGAL, KORAT MOSHE, COHEN, YIGAL, KORAT, MOSHE
Applicants: AGROGENE LTD, COHEN YIGAL, KORAT MOSHE, AGROGENE LTD., COHEN, YIGAL, KORAT, MOSHE
Application year: 1997
Main classification: C07C311
IPC codes: A01N37, A01N41, C07C233, C07C237, C07C311, C07D333