MXPA99006009A - Aminobutyric acid fungicides - Google Patents
Aminobutyric acid fungicidesInfo
- Publication number
- MXPA99006009A MXPA99006009A MXPA/A/1999/006009A MX9906009A MXPA99006009A MX PA99006009 A MXPA99006009 A MX PA99006009A MX 9906009 A MX9906009 A MX 9906009A MX PA99006009 A MXPA99006009 A MX PA99006009A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- aminobutyric acid
- ester
- alkyl
- benzenesulfonyl
- Prior art date
Links
- 230000000855 fungicidal Effects 0.000 title description 6
- 239000000417 fungicide Substances 0.000 title description 6
- BTCSSZJGUNDROE-UHFFFAOYSA-N GABA Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 title description 2
- 229960003692 aminobutyric acid Drugs 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 58
- 201000010099 disease Diseases 0.000 claims abstract description 15
- 230000002538 fungal Effects 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 370
- -1 thiophene-carbonyl Chemical group 0.000 claims description 186
- 125000000217 alkyl group Chemical group 0.000 claims description 95
- 229910052739 hydrogen Inorganic materials 0.000 claims description 69
- 239000001257 hydrogen Substances 0.000 claims description 69
- 241000196324 Embryophyta Species 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 35
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 24
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 23
- 125000003277 amino group Chemical group 0.000 claims description 23
- 125000002431 aminoalkoxy group Chemical group 0.000 claims description 23
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- 150000002367 halogens Chemical class 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 21
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- VQOIVBPFDDLTSX-UHFFFAOYSA-M sodium;3-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC(S([O-])(=O)=O)=C1 VQOIVBPFDDLTSX-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000009369 viticulture Methods 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
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
FUNGICIDES OF THE ACID AMINOBUTÍRICQ
INTRODUCTION The present invention refers to a novel method to protect plants from pathogenic attacks.
BACKGROUND OF THE INVENTION The use of threo-DL-β-methylaspartic acid and DL-β-aminobutyric acid for the control of root rot of peas, caused by Aphano yces euteiches has been described (Papavizas, Plant Disease Repórter, 48., 537-541 (1964), Papavizas, Plant Disease Reporter, 5: 1, 125-129 (1967) .The use of D-alanine, D and DL-leucine 'and DL-a-aminobutyric acid at 0.03M. was described to reduce the postilla in the apples, caused by Venturia inaequalis (Kuc et al., 49: 313-315, 1959) Van Andel, showed (Tijdschur, Plantenzie ten, 64: 307-327, 1958) that the DL -serine, D-serine (and, to a lesser extent, L-serine), phenylserine, DL-threonine, but not DL-a-aminobutyric acid or DL-β-aminobutyric acid, behave as chemotherapists against
the fungi Cladosporium cucumerinum in cucumbers (Ibid, page 318). Oort and Van Andel (1969, Mededel, Landsborowbagner Dpzoekingassta School, Staat Gent 25: 981-992) showed that DL-β-aminobutyric acid applied to tomato leaves protects these leaves against Phytophthora infestans (page 987). Several derivatives of DL-ß-aminobutyric acid and ß-aminocrotonic acid have been described in patent literature as fungicides, against Phytophthora infestans in tomato, and Plasmopara viticulture in grapes (German Patent No. 1,120,802). Israel's pending patent application, No.111, 824, describes the preparation and use of similar compounds that induce local and systemic resistance of crops against fungal diseases.
OBJECTIVES OF THE INVENTION It is an object of the present invention to provide compounds having an improved activity against fungi, in comparison with the compounds of the pending Israel patent application, No. 111,824.
COMPENDIUM OF THE INVENTION
We have found novel compounds of the formula (I): 1. A compound of the formula (I):
wherein: Ri and R2 are, independently, hydrogen, C, _8 alkyl, phenyl, and phenylalkyl; C, _4 / -R3 is straight or branched chain, or cyclic alkyl or alkenyl; alkoxyalkyl; halogenated alkyl, phenyl or benzyl; alkylphenyl; R and R5 are hydrogen or C? -8 alkyl; R6 is hydrogen; alkyl C? _8; C2-s alkanoyl; phenylalkyl
C1-4, benzoyl, in which the phenyl part is optionally substituted by one or more halogen atoms or C2-8 alkoxycarbonyl alkyl groups; CONHR8, wherein R8 is hydrogen, C? -8 alkyl, phenyl, phenylalkyl, C? _4; C2-4 phenylalkoxycarbonyl;
R7 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 its salts; and the harvest is selected from tomatoes, potatoes, cereals, grapes, melons, wheat and cucumbers. We have also found a novel method to protect a crop against diseases caused by fungi, by application to the crop or to its site, 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 chain, branched and cyclic forms, and preferably contains from one to ten carbon atoms. Ri and R2 are independently, preferably, hydrogen, methyl or phenyl, more preferably Ri is hydrogen or methyl and R2 is hydrogen. R3 is preferably alkyl or alkenyl, phenyl, benzyl or alkyl phenyl.
R 4 and 5 are, independently, preferably hydrogen or C 1 -4 alkyl, more preferably R 4 is hydrogen or methyl and R 5 is hydrogen. R6 is hydrogen, C5-alkyl; and more preferably hydrogen or methyl. R7 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;
n-octyl ester of D, L-N-p-methylbenzoyl-3-aminobutyric acid:
sec. -butyl ester of N-p-methylbenzoyl-3-aminobutyric acid:
n-octyl ester of D, L-N-3, 4-dichlorobenzoyl-3-aminobutyric acid:
2-chloroethyl-ester of DL-N-benzoyl-3-aminobutyric acid.
D, L-N-benzenesulfonyl-3-amino-N-benzyl-butyramide;
D-L-N-benzoyl-3-aminobutyric acid 2-chloroethyl ester;
N-p-methyl-benzoyl-3-aminobutyric acid 1-methyl-l-pentyl ester;
n-octyl ester of DL-N-benzenesulfonyl-3-aminobutyric acid;
sec. -butyl ester of N-benzenesulfonyl-3-aminobutyric acid;
N-Benzenesulfonyl-3-aminobutyric acid 1-methyl-1-butyl ester; heptyl-ester of D, L-N-4-methoxybenzoyl-3-aminobutyric acid;
D-L-N-3, 5-dimethylbenzoyl-3-aminobutyric acid heptyl ester.
heptyl-ester of D, L-N-2,6-difluorobenzoyl-3-aminobutyric acid;
heptyl-ester of D, L-N-4-tert. -butylbenzoyl-3-aminobutyric acid;
1-methylpentyl ester of D, L-N-4-methylbenzenesulfonyl-3-aminobutyric acid;
3-phenylpropyl-ester of D, L-N-benzenesulfonyl-3-aminobutyric acid;
1-methylpentyl ester of D, L-N-4-chlorobenzoyl-3-aminobutyric acid;
2- (Trichloromethyl) ethylester of D, L-N-benzenesulfonyl-3-aminobutyric acid;
1-methylpropyl ester of D, L-N-4-methylbenzenesulfonyl-3-aminobutyric acid; 1-methylbutyl-ester of D, L-N-3, 4-dimethylbenzoyl-3-aminobutyric acid;
D-L-N-3-methylbenzoyl-3-aminobutyric acid heptyl ester; 1-methylpentyl ester of D, L-N-3,5-dimethylbenzoyl-3-aminobutyric acid; heptyl-ester of D, L-N-2,6-dichlorobenzoyl-3-aminobutyric acid; 1-methylpentyl ester of D, L-N-2,6-dichlorobenzoyl-3-a-butyric acid; D-L-N-4-methylbenzoyl-3-aminobutyric acid 3-phenylpropyl ester;
D-L-N-3,5-dimethylbenzoyl-3-aminobutyric acid 2-chloroethyl ester;
2-chloroethyl-ester of D, L-N-4-methoxybenzoyl-3-aminobutyl acid;
2- (Trichloromethyl) ethyl ester of D, L-N-benzoyl-3-aminobutyric acid;
heptyl-ester of D, L-N-4-chlorobenzoyl-3-aminobutyric acid; l-Methyl-2-methoxyethyl-ester of D, L-N-benzenesulfonyl-3-aminobutyric acid;
heptyl-ester of D, L-N-2-methylbenzoyl-3-aminobutyric acid; D-L-N-4-methylbenzenesulfonyl-3-aminobutyric acid 2-bromoethyl ester;
heptyl-ester of D, L-N-4-methylbenzenesulfonyl-3-aminobutyric acid;
D, L-N-chlorobenzenesulfonyl-3-aminobutyric acid propyl ester; 2- (Trichloromethyl) ethyl ester of D, L-N-4-methylbenzoyl-3-aminobutyric acid;
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;
heptyl-ester of D, L-N-4-chlorobenzenesulfonyl-3-aminobutyric acid;
propyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid;
2-propenyl ester of D, L-N-benzoyl-3-aminobutyric acid;
D-L-N-4-methylbenzoyl-3-aminobutyric acid 1-methylhexyl ester; 1-methyldecanoyl ester of D, L-N-4-methylbenzoyl-3-aminobutyric acid; heptyl-ester of D, L-N-3, 4-dimethylbenzoyl-3-aminobutyric acid;
1-methylpentyl ester of D, L-N-4-methylbenzoyl-3-aminobutyric acid; D, L-N-2-methylaminobenzoyl-3-aminobutyric acid methyl ester; 1-methylpentyl ester of D, L-N-4-chlorobenzenesulfonyl-3-aminobutyric acid;
3-phenylpropyl-ester of D, L-N-benzenesulfonyl-3-aminobutyric acid;
1-methylpentyl ester of D, L-N-2-methylamin benzoyl-3-aminobutyric acid;
3, 5-dichlorophenyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid;
octyl ester of DL, N-4-2-thiophenebenzoyl-3-aminobutyric acid;
1-methylpentyl ester of D, -N-4-2-thiophenebenzoyl-3-aminobutyric acid, octyl ester of D, L-N-3,4-dimethylbenzoyl-3-aminobutyric acid.
Production Methods The novel compounds encompassed by the present invention are structurally related to the known compounds and can be prepared easily or by derivatizing the known compounds or by modifying processes for preparing the known compounds, as required. These procedures will be evident
of the experts in the field. The following procedures are illustrative. Compounds of the formula (I):
wherein Rx and R4_7 have the above definitions, and R3 represents hydrogen or C? _8 alkyl, can be obtained from 225-aminobutyric acid. To prepare compounds of the formula (I), where
Rs and R7 are as previously defined, the ß-aminobutyric acid is reacted with the NR7H2, in which R7 has the previous definitions. Reactions of this type are described in the literature, for example by A. Zilkha and J. Rivilin, J. Org.Chem. 1957, 23, 94. The present compounds were found to be effective against late blight in potatoes and tomatoes, powdery mildew in cereals, pubescent mildew in cucumbers, melons and grapes.
The present compounds of this invention will typically be applied to crops or their sites, before or after the start or after the initial signs of fungal attack and can be applied to the foliar surfaces of the crop. The amount of the active ingredient to be used will be sufficient to induce systemic resistance to the crop to control fungi and will vary depending on such factors as the fungal species to be controlled, the type of treatment (eg, spray) , sprinkling, seed treatment and soaking of the soil), the condition of the crop and the particular active ingredient used. As an application to the crop or its site, the compounds will be applied to crops with a dose rate of 0.1 to 5 kg / ha, preferably 0.2 to 2 kg / ha, with the application being repeated, as necessary, typically at intervals of each one to three weeks. Depending on the circumstances, the compounds of this invention can be used in association with other pesticides, for example fungicides, insecticides, acaricides, herbicides or growth regulators.
of the plants, in order to increase their activity or broaden their spectrum of activity. The compounds of this invention are conveniently employed as fungicidal compositions in association with acceptable carriers in agriculture or diluents. Such compositions also form part of the present invention. They may contain, apart from a compound of the formula (I), as active agent, other active agents, such as fungicides. They can be used in any form of application, solid or liquid, for example in the form of a wettable powder, an emulsion concentrate, a water dispersible ("flowable") suspension concentrate, a dusting powder, a granulate a delayed release form, which incorporates carriers, diluents and / or conventional auxiliaries. Such compositions can be produced in a conventional manner, for example by mixing the active ingredient with a carrier and other ingredients of the formulation. Particular formulations will be applied in spray forms, such as water dispersible concentrates or wettable powders may contain agents
surfactants, such as soaking or dispersing agents, for example the condensation product of formaldehyde with the naphthalene sulfonate, an alkylaryl sulfonate, a lignin sulfonate, a fatty acid sulfate, an ethoxylated alkylphenol and an ethoxylated fatty alcohol. In general, the formulations include from 0.01 to 90% by weight of the active agent, this active agent consists of at least one compound of the formula (I) or its mixtures with other active agents, such as the fungicides. The concentrated forms of the compositions generally contain between about 2 to 80%, preferably about 5 to 70% by weight of the active agent. The forms of application of the formulation can, for example, contain 0.01 to 20% by weight, preferably 0.01 to 5% by weight of the active agent.
Formulation Example I: Wettable Powder 50 parts by weight of a compound of the formula
(I) were ground with 2 parts of lauryl sulfate, 3 parts of sodium lignin sulfonate and 45 parts of finely divided kaolinite, with an average particle size below 5 microns. The resulting wettable powder, thus obtained, was diluted with water before use,
at a concentration between 0.01 and 5% of active ingredient. The resulting spray liquor can be applied as a foliar spray as well as by application of root soaking.
Formulation Example II: Emulsion concentrate 25 parts by weight of the compound of formula I, 65 parts of xylene, 10 parts of the mixed reaction product or of an alkylphenol with xylene oxide and calcium dodecylbenzenesulfonate, they were mixed well until a homogeneous solution was obtained. The resulting emulsion concentrate was diluted with water before use. Formulation Example III: Granulate (for soil treatments) On 94.5 parts by weight of quartz sand, in a rotary mixer, 0.5 parts by weight of a binder (non-ionic tenside) were sprayed and mixed thoroughly. 5 parts by weight of the compound of the formula (I), in powder form, were then added and mixed thoroughly to obtain a granular formulation with a particle size in the approximate range of 0.3 to 0.7 mm. The granulate can be applied by incorporation
on the ground adjacent to the plants to be treated. Formulation Example IV: Tuberous Seeds or Cultures 25 parts by weight of the compound of the formula
(I), 15 parts of dialkylphenoxy-poly- (ethyleneoxy) -ethanol, 15 parts of fine silica, 44 parts of fine kaolin, 0.5 parts of dye (for example crystal violet) and 0.5 parts of xanthan gum, were mixed and milled in a Contraplex mill at approximately 10,000 rpm, at an average particle size below 20 microns. The resulting formulation was applied to the seeds or tubers as an aqueous suspension in an apparatus suitable for that purpose. When the compound of the formula (I) is liquid, it is first absorbed onto the carriers, if desired with the aid of a small amount of a volatile solvent, such as acetone. The resulting powder is first allowed to dry when a solvent is used, then the other ingredients are added and the rest of the process is carried out. Formulation Example V: Soil Drip Irrigation
2 parts by weight of the compound of the formula (I) were dissolved in 1,000 parts of water. The resulting formulation was applied to the plant by drip irrigation. As previously mentioned, the compounds of the formula (I) are effective in activating or enhancing the crop defense system against diseases caused by fungi. Such activity can be demonstrated, by using the general procedures, by 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 no attempt is made to limit this invention to the particular embodiments. On the contrary, attempts are made to cover all alternatives, modifications and equivalents that may be included within the scope of the invention, as defined by the appended claims. Thus, the following examples, which include preferred embodiments, serve to illustrate the practice of this invention and it will be understood that the particular details shown are in exemplary form and for purposes of illustrative discussion of the preferred embodiments of the present invention only and
present in order to provide what is believed to be the most useful and easily understandable description of the procedures, as well as the principles and conceptual aspects of the invention.
EXAMPLES Example 1; D, -N-Benzenesulfonyl-3-apino N-benzyl-butyramide To 6.0 g of ß-aminobutyric acid in 20 ml of water, 5.4 g of NaOH dissolved in 26 ml of water were added. 10.3 g of benzenesulfonyl chloride were added in
36 ml of dichloroethane, at room temperature, during
minutes. The mixture was stirred for 10 minutes at room temperature and heated at 68 ° C for 4 hours. The phases were separated, and the aqueous phase was acidified with
HCl (concentrated) at a pH of 2.5. After extraction with dichloroethane (DCE), DL-N-benzenesulfonyl-3-aminobutyric acid crystallized from the organic phase. 6.7 g. Melting point (m.p.) of 125-127.4 ° C. To 7.7 g of compound I, in 80 ml of dichloroethane, 7.5 g of PC15 were added in small portions, keeping the temperature of the mixture at 5 ° C.
The mixture was allowed to warm to room temperature and was stirred for 5 hours. Petroleum ether 60-80 (400 mL) was added, the chloride was filtered and dried, yielding 7.3 g of the product (II). To 3.0 g of the acid chloride (II) in 30 ml of DCE, 2.3 g of benzylamine were added in 5 ml of DCE, for 10 minutes at 10-15 ° C. The mixture was heated at 50 ° C for 7 hours. 30 ml of water were added, the organic phase was separated and after concentration of the solution, the product precipitated. 2.66 g, p.f. 105-107 ° C. The spectroscopic methods of nuclear magnetic resonance (NMR) and mass (MS) confirmed the structure.
Example 2; D, L-N-benzenesulfonyl-3-aminobutyranilide To 3.0 g of the acid chloride (II) in 30 ml of DCE, 2.0 g of aniline in 5 ml of DCE was added for 10 minutes at 10-15 ° C. The mixture was heated at 50 ° C for 7 hours. 30 ml of water were added and the organic phase was separated. Evaporation of the solvent gave 3.5 g of the product. Recrystallization from toluene gave 2.8 g, m.p. 130-132 ° C. The spectroscopic methods of NMR and MS confirmed the structure.
Example 3; n-octyl ester of D, L-N-p-methyl-benzoyl-3-aminobutyric acid To 2.0 g of ß-aminobutyric acid in 9 ml of water, 3.4 g of NaOH in 9 ml of water were added. Then 3.0 g of p-toluoyl chloride in 15 ml of DCE was added, during 20 minutes, at room temperature. The mixture was heated at 62 ° C for 7 hours. The phases were separated and the aqueous phase was acidified with HCl (concentrated) to a pH of 2.0-2.5. The compound precipitated; decanting and recrystallization with water gave, after trituration with the DCE, 3.3 g, m.p. 115-118 ° C, of D, L-p-methylbenzoyl-3-aminobutyric acid (III). To 3.0 g of the acid (III) in 35 ml of DCE, 3.2 g of PC15 were added in small portions, maintaining the temperature of the mixture at 10-15 ° C. The mixture was allowed to warm to 25 ° C and was stirred for 7 hours. Petroleum ether 60-80 (280 ml) was added and the oil separated. Decanting the solvent and adding 50 ml of petroleum ether gave a crystalline compound. After filtration, 2.5 g of the IV acid chloride were obtained.
To the IV chloride, in 25 ml of DCE, 4.1 g of n-octanol were added in 5 ml of DCE, for 20 minutes at 30 ° C. The mixture was heated at 65 ° C for 6 hours. After distillation, 25 ml of DCE were added, washed with 3x of 10 ml of 2% sodium bicarbonate and dried over MgSO4. Evaporation of the solvent gave 2.1 g, m.p. 41-42 ° C, of the product, The NMR and MS spectra confirmed the structure.
Example 4; Secondary butyl ester of N-p-methyl-benzoyl-3-aminobutyric acid
Method A A 2.6 g of the IV chloride in 25 ml of DCE, 2.3 g of 2-butanol in 5 ml of DCE were added, during 10 minutes at 25 ° C. The mixture was heated at 65 ° C for 6 hours. After distillation, 25 ml of DCE were added, washed with 2% sodium bicarbonate and dried over MgSO4. Evaporation of the solvent gave 2.2 g of the product. Spectroscopic methods of NMR and MS confirmed the structure.
Method B
The mixture of 2.0 g of D, L-p-methylbenzoyl-3-aminobutyric acid (III), 0.85 g of 2-butanol, 30 ml of toluene and 0.04 g of H2SO4 (concentrate) was heated under reflux for about 7 hours. The water formed in the reaction was removed by azeotropic distillation. The cooled reaction mixture was washed twice with 15 ml of water, 2% sodium bicarbonate and dried over MgSO4. Distillation of the solvent gave 1.7 g of the ester.
Example 5_? n-octyl ester of D.L-N-3, 4-dichlorobenzoyl-3-aminobutyric acid
To 1.5 g of ß-aminobutyric acid in 5 ml of water, 2.5 g of NaOH in 6.4 ml of water were added. Then 3.0 g of 3,4-dichloro-benzoyl chloride in 10 ml of DCE was added for 10 minutes at room temperature. The mixture was heated at 65 ° C for 6.5 hours. The phases separated. The aqueous phase was washed twice with 15 ml of DCE and acidified with HCl (concentrated) to a pH of 1.5 to 2.0. The compound was filtered. 3.1 g, m.p. of 143-146 ° C. To 2.5 g of compound V in 35 ml of dichloroethane
(DCE), 2.2 g of PCL5 were added in small portions, maintaining the temperature of the mixture at 10-15 ° C. The
The mixture was allowed to warm to 25 ° C and stirred for 7 hours. Petroleum ether 60.80 was added, and the acid chloride precipitated, filtered and dried to give 1.5 g. To the chloride, in 25 ml of DCE, 2.0 g of n-octanol were added in 5 ml of DCE, for 10 minutes, at 20 ° C. The mixture was heated at 65 ° C for 7 hours. After distillation, 25 ml of DCE was added, washed with 2% sodium bicarbonate and dried over MgSO4. Evaporation of the solvent gave 2.0 g of the title compound. The spectroscopic methods of NMR and MS confirmed the structure.
Example 6: D-L-N-4-chlorobenzoyl-3-aminobutyric acid 2-chloro ethyl ester
To 3.0 g of aminobutyric acid in 7 ml of water, 3.4 g of NaOH in 8.7 ml of water were added. Then 3.1 g of p-chlorobenzoyl chloride in 15 ml of DCE was added, for 15 minutes at 10-15 ° C. The mixture was heated at 60 ° C for 7 hours. The phases were separated and the aqueous phase was washed twice with 15 ml of DCE, and acidified with HCl (concentrated) to a pH of 1.5-2.0. The compound was filtered and recrystallized with water. 3.94 g of DL-p-chlorobenkoyl-3-aminobutyric acid (VI) were obtained.
To 3.0 g of the VI acid, in 25 ml of DCE, 2.93 g of PCL5 were added in small portions, keeping the temperature of the mixture at 8-10 ° C. The mixture was allowed to warm to 25-27 ° C and stirred for 7 hours. Petroleum ether 60-80 (150 mL) was added, the chloride was filtered and dried by supplying 2.7 g of (VII). To 2.5 g of the acid chloride VII in 20 ml of DCE, 2-chloroethanol was added in 5.0 ml of DCE, for 10 minutes, at 15-17 ° C. The mixture was heated at 65 ° C for 7 hours. After distillation, 35 ml of DCE was added and washed with 2% sodium bicarbonate. Evaporation of the solvent gave 1.73 g of the product. Crystallization of cyclohexane gave 0.5 g, m.p. 80-81 ° C. The spectroscopic methods of NMR and MS confirmed the structure.
Example 7: N-benzenesulfonyl-3'-aminobutyric acid n-octyl ester
The mixture of 2.0 g of DL-N-benzenesulfonyl-3-aminobutyric acid (I), 1.78 g of n-octanol, 30 ml of toluene and 0.04 g of H2SO4 (concentrate) was heated under reflux for about 3 hours. The water formed in the reaction was removed by azeotropic distillation. The cooled reaction mixture was washed twice with bicarbonate
2% and dried over magnesium sulfate. Distillation of the solvent and alcohol yielded 2.0 g of the product, which was confirmed by spectroscopy.
Example 8: Secondary butyl ester of N-benzenesulfonyl-3-aminobutyric acid
The mixture of 2.0 g of DL-N-benzenesulfonyl-3-aminobutyric acid (I), 1.0 g of 2-butanol, 30 ml of toluene and 0.04 g of H2SO4 (concentrate) was heated under reflux for about 6 hours. The water formed in the reaction was removed by azeotropic distillation. The cooled reaction mixture was washed twice with 2% sodium bicarbonate, and dried over magnesium sulfate. Distillation of the solvent and alcohol provided 1.8 g of the product, which was confirmed by spectroscopy.
Example 9 N-Benzenesulonyl-3-aminobutyroic acid 1-methyl-1-butyl ester
The mixture of 2.0 g of DL-N-benzenesulfonyl-3-aminobutyric acid (I), 1.2 g of 2-pentanol, 30 ml of toluene and 0.04 g of H2SO4 (concentrate) was heated under reflux for about 6 hours. The reaction was treated as
in the previous example, 2.0 g of the ester was obtained, which was formed by spectroscopy.
Example 10: N-p-methylbenzoyl-1-aminobutyric acid 1-methyl-l-pentylester
The mixture of 2.0 g of Dl-p-methylbenzoyl-3-aminobutyric acid (III), 1.6 g of 2-hexano1, 30 ml of toluene and 0.04 g of H2SO4 (concentrate), was heated under reflux for about 7 hours. The water formed in the reaction was removed by azeotropic distillation. The cooled reaction mixture was washed with 3x15 ml of water, 2x15 ml of 2% sodium bicarbonate and dried over MgSO4. After distillation of the solvent and alcohol, 2.2 g of the ester was obtained, which was confirmed by spectroscopy.
Example 11; 2-chloroethyl esters of DL-N-benzoyl-3-aminobutyric acid
To 1.6 g of the DL-N-benzoyl-3-aminobutyric acid chloride, prepared in an analogous manner as the acid chloride VII (Example 6), in 25 ml of DCE, 2.5 g of the 2-chloroethanol were added in 5 ml. of DCE, for 10 minutes, at 19-20 ° C. The mixture was heated to 65-67 ° C for about 7 hours. After the distillation
of solvent and alcohol, 20 ml of DCE was added and washed with 2% sodium bicarbonate. Evaporation of the solvent gave 1.4 g of the product, confirmed by spectroscopy.
Example 12: N-b-benzenesulfonyl-3-aminobutyric acid 2-methyl-2-methoxy ethyl ester. To 6.0 g of ß-aminobutyric acid in 20 ml of water, 5.4 g of NaOH, dissolved in 25 ml of water, were added. 10.3 g of benzenesulfonyl chloride in 36 ml of dichloroethane were added at room temperature for 15 minutes. The mixture was stirred for 10 minutes at room temperature and heated at 68 ° C for 4 hours. The phases were separated and the aqueous phase was acidified with HCl (concentrated) to a pH of 2.5. After extraction with dichloroethane, the n-benzenesulfonyl-3-aminobutyric acid crystallized from the organic phase. 6.7 g, p.f. of 125-127 ° C. to 7.7 g of n-benzenesulfonyl-3-aminobutyric acid in 80 ml of DCE, 7.5 g were added in small portions keeping the temperature of the mixture at 5 ° C. The mixture was allowed to warm to room temperature and was stirred for 6 hours. Petroleum ether 60-80 (400 mL) was added, the chloride was filtered and dried giving 7.3 g of the chloride
of acid. The 2.0 g of the acid chloride in 30 ml of DCE was added to the 1-methoxy-2-propanol, dissolved in 5 ml of DCE at 10-15 ° C. The mixture was heated at 63-65 ° C for 6.5 hours. The reaction was washed twice with 20 ml of water and 2% sodium bicarbonate and dried over. MgSO 4 and the distillation of the solvent and the excess of alcohol provided 1.75% of the product. The structure was confirmed by MS and NMR spectroscopic methods. By proceeding as described above, using the appropriate starting materials, compounds 19, 29, 36 and 37 were prepared.
Example 13: Methyl ester of N-2-methylammonobenzoyl-3-aminobutyric acid. The mixture of 17.7 g of N.methystatic anhydride, 10.3 g of β-aminobutyric acid, 1.5 g of triethylamine and 150 ml of toluene was refluxed for 7 hours. The solids were removed by filtration and the N-2-methylaminobenzoyl-3-aminobutyric acid crystallized from the filtrate. The compound was filtered and washed with water and toluene, where 5.4 g was obtained. To 2.0 g of N-2-methylaminobenzoyl-3-aminobutyric acid in 19 g of methanol, 2.3 g of thionyl chloride were added at room temperature. The mixture was heated at 60 ° C for 6.5 hours.
After the distillation of methanol, 50 ml of dichloroethane was added. The solution was washed twice with 25 ml of 2% sodium bicarbonate, 25 ml of water and dried over MgSO4. After evaporation of the solvent, 1.8 g of the product were obtained. The spectroscopic methods of NMR and MS confirmed the structure.
Example 14: N-4-methoxy-benzoyl-3-aminobutyl acid n-heptyl ester To 9.2 g of ß-aminobutyric acid in 32 ml of water, 15.6 g of NaOH in 40 ml of water were added. Then 16.6 g of 4-methoxybenzoyl chloride in 60 ml of dichloroethane (DCE) were added for 20 minutes at 15-20 ° C. The mixture was heated at 65 ° C for 7.5 hours. The phases were separated and the aqueous phase was acidified with HCl (concentrated) to a pH of 2 to 2.5. The compound precipitated.
18.7 g of n-4-methoxy-benzoyl-3-aminobutyric acid, m.p. of 112-116 ° C, after recrystallization with the DCE. The mixture of 2.0 g of n-4-methoxy-benzoyl-3-aminobutyric acid, 1.6 g of 1-heptanol, 30 ml of toluene and 0.04 g of H2SO4 (concentrated, heated under reflux for 7 hours. formed in the reaction was separated by azeotropic distillation.
cooled it was washed twice with 2.5 ml of water. After the evaporation of the solvent. The excess alcohol was distilled at 90 ° C (0.4 mm Hg) and 0.8 g of the product was obtained. The spectroscopic methods of NMR and MS confirmed the structure.
Example 15: N-benzoyl-3-aminobutyric acid cyclohexyl ester The mixture of 2.0 g of n-benzoyl-3-aminobutyric acid, 1.6 g of cyclohexanol, 30 ml of toluene and 0.04 g of H2SO4 (concentrate) was heated under After refluxing for 2 hours, the water formed in the reaction was removed by azeotropic distillation. The cooled solution was washed with water and twice with 30 ml of 2% sodium bicarbonate. After evaporation of the solvent and distillation of the excess alcohol at 50 ° C, 0.4 mm Hg, 1.5% of the oily product was obtained, which solidified, m.p. 60-63 ° C. The structure was confirmed by MS and NMR spectroscopic methods.
Example 16. N-benzoyl-3-aminobutyric acid 2-propenyl ester (compound 42) The mixture of 10 g of n-benzoyl-3-aminobutyric acid, 4.8 g of allyl alcohol, 70 ml of toluene and
0. 2 g of H2SO4 (concentrated, heated under reflux for 7 hours) The water formed in the reaction was removed by azeotropic distillation, the solution was washed with water, 2% sodium bicarbonate and dried over MgSO4. of the solvent, 5.0% of the product was obtained The MS and NMR spectroscopy methods approved the structure Compounds 12-18, 20-28, 30-35, 37-46 and 48 were prepared in manners similar to those described in Examples 13-16, using suitable starting materials Activity against late blight in potatoes and tomatoes For the following experiments, potted potato plants, six weeks old (Solanum tuberosum, Alpha grower) or tomato plants were used in pots, 4 weeks old (Lycopersicon esculentum, Florida basket cultivator) The plants were sprayed with the test compound and two days later challenged by inoculation with the late blight fungus, Phytophthora infestans. was carried out as follows: 1. The fungi grew on slices of potato tubers, at 15 ° C, for 7 days.
The spores produced on the slices of tubers were collected in cold distilled water (4 ° C) and their concentration adjusted to 2.5-3 x 103 spores / ml. The spore suspension was sprayed onto the treated plants. The untreated plants were also inoculated as controls. The inoculated plants were placed in a dew chamber at 18 ° C, for 20 hours, and then transferred to a growth chamber at 20 ° C with a photoperiod of 12 hours of light and a relative humidity of 60-70%. 4-7 days after inoculation, the intensity of the developed disease was visually activated by assessing the percentage of the foliage area destroyed by the fungi. The control efficiency achieved by the spray treatment was calculated in relation to the intensity of the disease seen on the control plants. For example, when the% foliage area destroyed was 90% in the control plants and 10% in the treated plants, the control efficiency was calculated as:
(1 - 10) x 100 = 88.0% 90
The results are shown in Tables 1 and 2
Table 1. Activity of some BABA derivatives against late blight caused by Phytophthora infestans in potato and tomato plants
Control Efficiency%
P a p a T o m a t e
Compounds 26.7.96 17.7.96 14.8.96 12.7.96 14.8.96 500 500 500 2000 2000 500 2000 2000 ppm ppm ppm ppm n ßßm -om 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 BABA derivatives against late blight caused by Phytophthora infestans in potatoes, 3-8 days after inoculation- Dosage: 200 ppm% Control Efficacy
of 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 Example Late blight in potato, caused by Phytophthora infestans, additional examples. Potato plants (cultivated variety), [ve] Alpha) were developed from tubers in 1 liter pots in the greenhouse. At 4 weeks after "sowing", when he had 3 to 4 shoots with 10 to 12 leaves, the plants were sprayed with the test solutions on their adaxial surfaces and incubated in growth cabinets at 20 ° C. Two days later, the sprayed plants were inoculated with a suspension of spores (2000 spores / ml) of P. infestans (corresponding type A2, resistant to metalaxyl). The inoculated plants were placed in a relative humidity of 100% in the dark, for 20 hours, and then returned to the growth cabinet at 20 ° C during the production of symptoms. The percentage of leaf area covered with blight symptoms was assessed visually 6 days after inoculation. The control efficacy was calculated in relation to the inoculated control plants. The results are shown in Table 3.
Table 3 Activity of some BABA derivatives against late blight caused by Phytophthora infestans in potatoes. 6 days after the inoculation. Dose: 500 ppm CH3C (H) NHR7CH2C (O) -0R3 Compound Rr R3 (%) Control Efficacy, 6d 12 4-CH3OC6H4CO (CH2) 5CH3 89 13 6.5- (CH6) 2C6H5CO (CH2) sCH3 84 48 C4H3SCO (CH2) CH3 82 14 2.6-F2C6H5CO (CH2) 6CH3 79 15 4-C (CH6) 5C6H4CO (CH2) dCH3 79 16 4-CH6C6H4SO2 CH (CH5) (CH2) 5CH3 79-50 4-CIC6H5SO2 CH (CH3 ) (CH2) 3CH3 77 17 C8H5SO2 (CH2) 3C5H = 5 76 18 4-CIC6H5CO CH (CH3) (CH2) 3CH3 76 51 C6HdSO2 (CH2) 3OC6H5 76 49 2-C4H3SCO CH (CH3) (CH2) 3CH3 75 19 C8HsSO CH CCI3 75 20 4-CH5C6H4SO2 CH (CH3) CH2CH3 75 52 2-CH3NHC6H4C0 CH (CH3) (CH2) 3CH3 74 21 3.4diCH6C6H5CO CH (CH3) CH2) 2CH3 73 22 3-CH5C6H4CO (CH2) 6CH3 70
Late blight in tomato, caused by Phytophthora infestans Tomato plants (ve Baby) were grown from seeds in 0.2 liter pots in the greenhouse. At 3 weeks, after sowing, when the plants had 6 leaves, they were sprayed with the test solution, on their adaxial surfaces. They were inoculated and then handled and evaluated for the development of the disease, as described in Section I above. The results are shown in Table 4.
Table 4 Activity of some BABA derivatives against late blight caused by Phytophthora infestans in tomato, 7 days after inoculation. Dose: 500 ppm CH3C (H) NHR7CH2C (0) -0R3
Compound Rr R3 (%) Control Efficacy, 7d 35 CIC6H5SO2 CH2CH2CH = 3 81 36 4-CH3C6H4CO Cri2CCI3 81 37 4-CH3C6H4CO cyclohexyl 78 38 C6H5CO cyclohexyl 78 39 C6HdSO2 cyclohexyl 75
52 2-CH3NHC6H4CO CH (CH3) (CH2) 3CH3 75
II. Activity against powdery mildew in cereals In the following experiments, potted wheat plants, 10 days old (Triticum asetivum, Atir cultivator) and barley plants (Hhordeum vulgaris, Amidon cultivator) were used. The plants were sprayed with the test compounds and two days after inoculation with the fungal pathogens of powdery mildew. The wheat was inoculated with Erysiphe granims tritici. The barley was inoculated with Erysiphe aranims hordei of powdery mildew. The inoculation was done by shaking the infected donor plants, collecting abundant conidia on the treated plants. The untreated plants were also inoculated as controls. The inoculated plants were placed inside a growth chamber at 20-22 ° C, with a photoperiod of 1 hour at 50-60% RH. At 9-10 days after inoculation, the intensity of the
Disease was evaluated visually by estimating the percentage of leaf area occupied by the fungal colonies. The control efficiency achieved by the sprayed test compound was calculated in relation to the intensity of the disease seen on the control plants. For example, when the% of the foliage area occupied by the fungal colonies was 90% in the treated plants, the control efficiency was calculated as: (1 - 10) x 100 = 88.0% 90
The results are shown in Table 5.
Table 5. Activity of some BABA derivatives against powdery mildew, caused by Erysiphe gra inis. in cereals% of Control Efficiency
Barley 17.9.96 Triao 7.8.96 Compound 500 ppm 2000 ppm 500 ppm 2000 ppm Example 1 25 75 Example 6 62 75 Example 4 87 95 96 96
Example 5 82 85 76 92
Powdered wheat mildew, caused by Erysiphe graminis tritici. additional examples Wheat plants (see Shafir) were grown from seeds in the greenhouse, 30 plants per 0.2 liter pot. When the first leaf was fully developed, the plants were sprayed with the test solutions and placed in a growth cabinet at 20 ° C. Two days after spraying, the plants were sprinkled with conidia of E. graminis tritici, so that about 100 spores were placed on 1 cm2 of leaf area (both surfaces). The inoculated plants were placed in a growth cabinet at 20 ° C, for 7 days, and the number of colonies developed per plant was counted. The control efficacy was calculated in relation to the number of colonies developed in the untreated inoculated control plants. The results are shown in Table 6.
Table 6 Activity of some BABA derivatives against powdery mildew caused by Erysiphe sraminis in wheat. 7 days after inoculation. Dose: 500 ppm CH3C (H) NHR7CH2C (0) -0R3 Compound R7 Rs (%) Control Efficacy, 7d 38 C6H5CO cyclohexyl 100 53 C6H5SO2 3.5- (CI) 2C6H3 100 50 4-CIC6H4SO2 CH (CH3) (CH2 ) 3CH3 92 12 4-CH3OC6H4CO (CH2) 5CH3 85 32 2-CH3C6H4CO (CH2) gCH3 83 16 4-CH3C6H4S02 CH (CH3) (CH2) 5CH3 83 35 4-CIC6H4SO2 CH3CH2CH3 81 47 2-CH3NHC6H4CO CH3 81 41 C6iH4SO2 CH3CH2CH3 11 42 C6H5CO CH2CH =: CH2 11 43 4-CH3C6H4CO CH (CH3) (CH2) 4CH3 75 44 4-CH3C6H4CO CH (CH3) (CH2) 6CH3 74 13 3.5- (CH3) 2C6H3CO (CH3) ßCH3 72 45 3, 4-diCH3C6H3CO (CH3) 6CH3 71 46 4-CH3C6H4CO CH (CH3) (CH2) 3CH3 69 54 3.4- (CH3) 2C6H3CO (CH2) CH3 69
III Pubescent mildiú in cucumber and melon, .caused by Pseudosperonospora cubensis Cucumber plants (see Dlila) and melon plants (ve Ein Dor) were grown from seeds in 0.2 liter pots in the greenhouse. At 3 weeks after sowing, when they had 3 true leaves, they were inoculated with a spore suspension (1000 spores / ml) of P. cubensis (resistant to metalaxyl) and placed at 100% relative humidity in the dark, during 20 hours. Then they were placed in a growth cabinet for 7 days and evaluated in the development of the disease. The percentage of the area of the leaf covered with the symptoms of the disease was evaluated and the efficacy of the control was calculated in relation to the inoculated control plants. The results are shown in Tables 7 and 8.
Table 7 Activity of some BABA derivatives against pubescent mildew, caused by Pseudoperonospora cubensis in melon. 7 days after inoculation Dose: 500 ppm CH3C (H) NHR7CH2C (O) -0R3 Compound Rr R3 (%) Control Efficacy, 7d 12 4-CH3OC6H4CO (CH2) eCH3 100 15 4-C (CH3) 3C6H4CO (CH2 ) 6CH3 97 17 C6rl5SO2 (CH2) 3C6H5 87 18 4-CIC6H4CO CH (CH3) (CH2) 3CH3 87, 51 C6HsSO2 (CH2) 3C6H5 87 22 3-CH3C6H4CO (CH2) 6CH3 83
3.4-CI2C6H3CO CH (CH3) (CH2) 3CH3 80 32 2-CH3C6H4CO (CH2) CH3 77 33 4-CH3C6H4SO2 CH CH2Br 75 27 3.5- (CH3) 2C6H3CO CH CH2CI 73 23 3.5- (CH3 ) 2C6H3CO CH (CH3) (CH2) 3CH3 73 34 4-CH3C6H4SO2 (CH2) 8CH3 70 29 C6H5CO CH2CCI 70
Table 8 Activity of some BABA derivatives against pubescent downy mildew caused by Pseudoperonospora cubensis in cucumber. 7 days after inoculation Dosage: 500 ppm
CH3C (H) NHR7CH2C (O) -0R3
Compound Rr R3 (%) Control Efficacy, 7d 52 2-CH3NHC6H4CO CH (CH3) (CH2) 3CH3 97 40 CIC6H5SO2 (CH2) 6CH3 82 36 4-CH3C6H4CO CH3CCI3 82 38 C6H5CO cyclohexyl 80 35 CIC6H5CO2 CH2Cri2CH3 77 37 4-CH3C6H4CO cyclohexyl 75 39 C6HsSO2 cycle exile 70
IV. Mildiú pubescent in grapes. caused by Plasmopara viticola Grape plants (ve Superior) of cuttings were cultivated and when they developed from 5 to 6 expanded leaves, they were sprayed with the test solutions on their surfaces of abaxial (lower) leaves. Two days after spraying, the plants were inoculated with the suspension of spores of P. viticola (104 spores / ml) on their lower surfaces of the leaves and placed in 100% relative humidity for 20 hours. The plants were then placed in growth cabinets at 20 ° C for 10 days. The development of the disease was evaluated according to the abaxial surface area of the leaf covered with fungal sporulation. This fungal sporulation was induced by placing the infected plants at 100% relative humidity, in the dark, for 48 hours. The results are shown in Table 9.
Table 9 Activity of some BABA derivatives against pubescent mildew, caused by Peronospora viticola. in grapes, 10 days after inoculation. Dose: 500 ppm CH3C (H) NHR7CH2C (O) -0R3
Compound Rr Ra (%) Control Efficacy, 10d 16 4-CH3C6H4SO2 CH (CH3) (CH2) 3CH3 100 14 2.6-F2C6H3CO (CH2) eCH3 100 23 3.5- (CH3) 2C6H3CO CH (CH3) (CH2 ) 3CH3 100 20 4-CH3C6H4SO2 CH (CH3) CH2CH3 100 24 3.4-CI2C6H3CO (CH2) 6CH3 100 25 3.4-CI2C6H3CO CH (CH3) (CH2) 3CH3 100 26 4-CH3C6H4CO (CH2) 3C6Hg 99 15 4 -C (CH3) 3C6H4CO (CH2) ßCH3 97 27 3.5- (CH3) 2C6H3CO CH CH Cl 97 17 C6HsSO2 (CH2) 3C6H5 97 51 C8H5SO2 (CH2) 3C6H5 97 19 C6HsSO2 CH2CCI3 94 28 4-CH3OC6H4CO CH2CH CI 91 29 C6H5CO CH2CCI3 91 30 4-CIC6H4CO (CH2) 8CH3 91 18 4-CIC6H4CO CH (CH3) (CH2) 3CH3 91 31 CßH5SO2 CH (CH3) CH2OCH3 82
Claims (278)
- CLAIMS 1. A compound of the formula (I) wherein: a) Ri and R2 are, independently, hydrogen, C? -8 alkyl, phenyl and phenyl? C? _4; b) R3 is straight or branched chain, or cyclic alkyl or alkenyl C? -23; halogenated alkoxyalkyl, alkyl, phenyl or benzyl; alkylphenyl, • c) R4 and R5 are hydrogen or C? _8 alkyl, where at least one of R4 and R5 is C? 8 alkyl d) Rs is hydrogen; alkyl C? _8; C2.8 alkanoyl; phenylalkyl C? -, benzoyl, in which the phenyl part is optionally substituted by one or more halogen atoms or C2-8 alkoxycarbonyl alkyl groups; C0NHR8, wherein R8 is hydrogen, C? _8 alkyl, phenyl, C? -4 phenylalkyl; C2-4 phenylalkoxycarbonyl; e) R7 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 its salts; with the proviso that: when R8 is a methyl, ethyl or an unsubstituted benzyl group, then R7 is not a benzenesulfonyl group substituted by monoalkyl; and when R8 is a propyl group or a benzoyl group, R7 is not an unsubstituted benzoyl group or a benzoyl group substituted by dialkyl; and when R3 is a methyl or ethyl group, and R or R2 is a methyl, ethyl or benzyl group, R7 is not an unsubstituted benzoyl group; and when R3 is an ethyl group, R7 is not a 2-amino-5-iodo-benzoyl group or a 2-aminomethyl-5-iodo-benzoyl group.
- 2. A compound, according to the claim 1, in which Ri and R2 are independently hydrogen, R3 is straight or branched or cyclic alkyl or alkenyl C? 23; alkoxyalkyl, halogenated alkyl, phenyl or benzyl; alkylphenyl; R and R5 are, independently, hydrogen or C? _3 alkyl; R6 is hydrogen; R7 is benzenesulfonyl or benzoyl, optionally substituted by one or more halogen, alkyl groups, amino groups or alkoxy groups; or thiophene-carbonyl; and X is oxygen or -NH.
- 3. A compound, according to the claim 1, wherein Rx, R2, R5 and R6 are hydrogen; R3 is Cl-23 alkyl or alkenyl, straight or branched chain, or cyclic; alkoxyalkyl, halogenated alkyl, phenyl or benzyl; alkylphenyl or benzyl; R4 is methyl; and R7 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-benzenesulfonyl-3-amino-N-benzyl-butyramide.
- 5. A compound, according to claim 1, wherein the compound is D, L-N-benzenesulfonyl-3-aminobutyranilide.
- 6. A compound, according to claim 1, wherein the compound is the 2-chloroethyl ester of the acid D, L-N-p-chlorobenzoyl-3-aminobutyric acid.
- 7. A compound, according to claim 1, wherein the compound is the n-octyl ester of D, L-N-p-methylbenzoyl-3-aminobutyric acid.
- 8. A compound, according to claim 1, wherein the compound is sec. -butyl ester of N-p-methylbenzoyl-3-aminobutyric acid.
- 9. A compound, according to claim 1, wherein the compound is the n-octyl ester of D, L-N-3,4-dichlorobenzoyl-3-aminobutyric acid.
- 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-pentylester.
- 12. A compound, according to claim 1, wherein the compound is the n-octyl ester of DL-N-benzenesulfonyl-3-aminobutyric acid.
- 13. A compound, according to claim 1, wherein the compound is sec. -butyl ester of N-benzenesulfonyl-3-aminobutyric acid.
- 14. A compound, according to claim 1, wherein the compound is 1-methyl-l-butyl-ester of N-benzenesulfonyl-3-aminobutyric acid.
- 15. A compound, according to claim 1, wherein the compound is the heptyl ester of D, L-N-4-methoxybenzoyl-3-aminobutyric acid.
- 16. A compound, according to claim 1, wherein the compound is the heptyl ester of D, L-N-3,5-dimethylbenzoyl-3-aminobutyric acid.
- 17. A compound, according to claim 1, wherein the compound is the heptyl ester of D, L-N-2,6,6-difluorobenzoyl-3-aminobutyric acid.
- 18. A compound, according to claim 1, wherein the compound is the heptyl ester of D, L-N-4-tere acid. -butylbenzoyl-3-aminobutyric acid.
- 19. A compound according to claim 1, wherein the compound is 1-methylpentyl ester of D, L-N-4-methylbenzenesulfonyl-3-aminobutyric acid.
- 20. A compound, according to claim 1, wherein the compound is the 3-phenylpropyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 21. A compound, according to claim 1, wherein the compound is 1-methylpentyl ester of D, L-N-4-chlorobenzoyl-3-aminobutyric acid.
- 22. A compound, according to claim 1, in which the compound is 2- (trichloromethyl) ethyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 23. A compound, according to claim 1, wherein the compound is D, L-N-4-methylbenzenesulfonyl-3-aminobutyric acid 1-methylpropyl ester.
- 24. A compound, according to claim 1, wherein the compound is D, L-N-3,4-dimethylbenzoyl-3-aminobutyric acid 1-methylbutyl ester.
- 25. A compound, according to claim 1, wherein the compound is the heptyl ester of D, L-N-3-methylbenzoyl-3-aminobutyric acid.
- 26. A compound, according to claim 1, wherein the compound is 1-methylpentyl ester of D, L-N-3,5-dimethylbenzoyl-3-aminobutyric acid.
- 27. A compound, according to claim 1, wherein the compound is the heptyl ester of D, L-N-2,6-dichlorobenzoyl-3-aminobutyric acid.
- 28. A compound, according to claim 1, wherein the compound is 1-methylpentyl ester of D, L-N-2,6-dichlorobenzoyl-3-aminobutyric acid.
- 29. A compound, according to claim 1, wherein the compound is the 3-phenylpropyl ester of D, L-N-4-methylbenzoyl-3-aminobutyric acid.
- 30. A compound, according to claim 1, wherein the compound is the D-L-N-3,5-dimethylbenzoyl-3-aminobutyric acid 2-chloroethyl ester.
- 31. A compound, according to claim 1, wherein the compound is the 2-chloroethyl ester of D, L-N-4-methoxybenzoyl-3-aminobutyric acid. 32. A compound, according to claim 1, wherein the compound is 2-
- D, L-N-benzoyl-3-aminobutyric acid (trichloromethyl) ethyl ester.
- 33. A compound, according to claim 1, wherein the compound is 2- (trichloromethyl) ethyl ester of D, -N-benzoyl-3-aminobutyric acid.
- 34. A compound, according to claim 1, wherein the compound is 1-methyl-2-methoxyethyl-ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 35. A compound, according to claim 1, wherein the compound is the heptyl ester of D, L-N-2-methylbenzoyl-3-aminobutyric acid.
- 36. A compound, according to claim 1, wherein the compound is the 2-bromoethyl ester of D, L-N-4-methylbenzenesulfonyl-3-aminobutyric acid.
- 37. A compound, according to claim 1, wherein the compound is the heptyl ester of D, L-N-4-methylbenzenesulfonyl-3-aminobutyric acid.
- 38. A compound, according to claim 1, wherein the compound is the propyl ester of D, L-N-chlorobenzenesulfonyl-3-aminobutyric acid.
- 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 the cyclohexyl ester of D, L-N-4-methylbenzoyl-3-aminobutyric acid.
- 41. A compound according to claim 1, wherein the compound is the cyclohexyl ester of D, L-N-benzoyl-3-aminobutyric acid.
- 42. A compound, according to claim 1, wherein the compound is the cyclohexyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 43. A compound, according to claim 1, wherein the compound is the heptyl ester of D, L-N-4-chlorobenzenesulfonyl-3-aminobutyric acid.
- 44. A compound, according to claim 1, wherein the compound is the propyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 45. A compound, according to claim 1, wherein the compound is the 2-propenyl ester of D, L-N-benzoyl-3-aminobutyric acid.
- 46. A compound, according to claim 1, wherein the compound is 1-methylhexyl-ester of D, L-N-4-methylbenzoyl-3-aminobutyric acid.
- 47. A compound, according to claim 1, wherein the compound is D, L-N-4-methylbenzoyl-3-aminobutyric acid 1-methyldecanoyl ester.
- 48. A compound, according to claim 1, wherein the compound is the heptyl ester of D, L-N-3,4-dimethylbenzoyl-3-aminobutyric acid.
- 49. A compound, according to claim 1, wherein the compound is 1-methylpentyl ester of D, L-N-4-methylbenzoyl-3-aminobutyric acid.
- 50. A compound, according to claim 1, wherein the compound is the methyl ester of D, L-N-2-methylaminobenzoyl-3-aminobutyric acid.
- 51. A compound, according to claim 1, wherein the compound is 1-methylpentyl ester of D, L-N-4-chlorobenzenesulfonyl-3-aminobutyric acid.
- 52. A compound, according to claim 1, wherein the compound is the 3-phenylpropyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 53. A compound, according to claim 1, wherein the compound is 1-methyl pentyl ester of D, L-N-2-methylaminobenzoyl-3-aminobutyric acid.
- 54. A compound, according to claim 1, wherein the compound is 3,5-dichlorophenyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 55. A compound, according to claim 1, wherein the compound is 1-methylpentyl ester of D, L-N-4-methylaminobenzoyl-3-aminobutyric acid.
- 56. A compound, according to claim 1, wherein the compound is the octyl ester of D, L-N-3,4-dimethylbenzoyl-3-aminobutyric acid.
- 57. A compound, according to claim 1, wherein the compound is the octyl ester of D, L-N-2-thiophenecarbonyl-3-aminobutyric acid.
- 58. A compound, according to claim 1, wherein the compound is 1-methylpentyl ester of D, L-N-2-thiophenecarbonyl-3-aminobutyric acid.
- 59. A method for protecting a crop against fungal diseases, this method comprises applying to the crop or to its site, a composition containing an effective amount of a compound having the formula (I): wherein: a) Ri and R2 are, independently, hydrogen, C? -8 alkyl, phenyl and phenyl? C? _4; b) R3 is straight or branched chain, or cyclic alkyl or alkenyl C? -23; halogenated alkoxyalkyl, alkyl, phenyl or benzyl; alkylphenyl; c) R and R5 are hydrogen or C? -8 alkyl, wherein at least one of R4 and R5 is C? _8 alkyl; d) R6 is hydrogen; alkyl C? -8; C2-8 alkanoyl; C? -4 phenylalkyl, benzoyl, in which the phenyl part is optionally substituted by one or more halogen atoms or C2-8 alkoxycarbonyl alkyl groups; CONHR8, wherein R8 is hydrogen, C? _8 alkyl, phenyl, phenylalkyl C? _4; C2-4 phenylalkoxycarbonyl; e) R7 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 its salts.
- 60. A method, according to claim 59, wherein Ri and R2 are, independently, hydrogen, R3 is C-23 straight or branched chain, or cyclic alkyl or alkenyl; alkoxyalkyl; halogenated alkyl, phenyl or benzyl; alkylphenyl; R and R5 are, independently, hydrogen or C? _3 alkyl; Rs is hydrogen; R7 is benzenesulfonyl or benzoyl, optionally substituted by one or more halogen, alkyl groups, amino groups or alkoxy groups; or thiophene-carbonyl; and X is oxygen or -NH.
- 61. A method, according to claim 59, wherein Rl t R2, R5 and Rs are hydrogen; R3 is straight or branched chain, or cyclic, alkyl-alkenyl Cl-23 alkyl-alkoxyalkyl; halogenated alkyl, phenyl or benzyl; alkylphenyl or benzyl; R4 is methyl; and R7 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-benzenesulfonyl-3-amino-N-benzyl-butyramide.
- 63. A method, according to claim 59, wherein the compound is D, L-N-benzenesulfonyl-3-aminobutyranilide.
- 64. A method, according to claim 59, wherein the compound is the D-L-N-p-chlorobenzoyl-3-aminobutyric acid 2-chloroethyl ester.
- 65. A method, according to claim 59, wherein the compound is the n-octyl ester of D, L-N-methylbenzoyl-3-aminobutyric acid.
- 66. A method, according to claim 59, wherein the compound is sec. -butyl ester of N-p-methylbenzoyl-3-aminobutyric acid.
- 67. A method, according to claim 59, wherein the compound is the n-octyl ester of D, L-N-3,4-dichlorobenzoyl-3-aminobutyric acid.
- 68. One method, according to the claim 59, in which 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-pentylester.
- 70. A method, according to claim 59, wherein the compound is the n-octyl ester of DL-N-benzenesulfonyl-3-aminobutyric acid.
- 71. A method, according to claim 59, wherein the compound is sec. -butyl ester of N-benzenesulfonyl-3-aminobutyric acid.
- 72. A method, according to claim 59, wherein the compound is N-benzenesulfonyl-3-aminobutyric acid 1-methyl-l-butyl ester.
- 73. A method, according to claim 59, wherein the compound is the heptyl ester of D, L-N-4-methoxybenzoyl-3-aminobutyric acid.
- 74. A method, according to claim 59, wherein the compound is the heptyl ester of D, L-N-3,5-dimethylbenzoyl-3-aminobutyric acid.
- 75. One method, according to the claim 59, in which the compound is the heptyl ester of D, L-N-2,6,6-difluorobenzoyl-3-aminobutyric acid.
- 76. A method, according to claim 59, wherein the compound is the heptyl ester of D, L-N-4-tert. -butylbenzoyl-3-aminobutyric acid.
- 77. A method, according to claim 59, wherein the compound is 1-methylpentyl ester of D, L-N-4-methylbenzenesulfonyl-3-aminobutyric acid.
- 78. A method, according to claim 59, wherein the compound is the 3-phenylpropyl ester of the acid D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 79. A method, according to claim 59, wherein the compound is D, L-N-4-chlorobenzoyl-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 acid 1-methylpropyl ester.
- 82. One method, according to the claim 59, in which the compound is D, L-N-3, 4-dimethylbenzoyl-3-aminobutyric acid 1-methylbutyl ester.
- 83. A method, according to claim 59, wherein the compound is the heptyl ester of D, L-N-3-methylbenzoyl-3-aminobutyric acid.
- 84. A method, according to claim 59, wherein the compound is 1-methylpentyl ester of D, L-N-3,5-dimethylbenzoyl-3-aminobutyric acid.
- 85. A method, according to claim 59, wherein the compound is the heptyl ester of D, L-N-2,6-dichlorobenzoyl-3-aminobutyric acid.
- 86. A method, according to claim 59, wherein the compound is 1-methylpentyl ester of D, L-N-2,6-dichlorobenzoyl-3-aminobutyric acid.
- 87. A method, according to claim 59, wherein the compound is the 3-phenylpropyl ester of the acid D, L-N-4-methylbenzoyl-3-aminobutyric acid.
- 88. A method, according to claim 59, wherein the compound is the D-L-N-3,5-dimethylbenzoyl-3-aminobutyric acid 2-chloroethyl ester.
- 89. One method, according to the claim 59, in which the compound is the 2-chloroethyl ester of D, L-N-4-methoxybenzoyl-3-aminobutyric acid.
- 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 the heptyl ester of D, L-N-4-chlorobenzoyl-3-aminobuiric acid.
- 92. A method, according to claim 59, wherein the compound is the L-methyl-2-methoxyethyl-ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 93. A method, according to claim 59, wherein the compound is the heptyl ester of D, L-N-2-methylbenzoyl-3-aminobutyric acid.
- 94. A method, according to claim 59, wherein the compound is the 2-bromoethyl ester of the acid D, L-N-4-methylbenzenesulfonyl-3-aminobutyric acid.
- 95. A method, according to claim 59, wherein the compound is the heptyl ester of D, L-N-4-methyl-benzenesulfonyl-3-aminobutyric acid.
- 96 One method, according to the claim 59, in which the compound is the propyl ester of D, L-N-chlorobenzenesulfonyl-3-aminobutyric acid.
- 97. A method, according to claim 59, wherein the compound is 2- (trichloromethyl) ethyl ester of D, L-N-4-methylbenzoyl-3-aminobutyric acid.
- 98. A method, according to claim 59, wherein the compound is the cyclohexyl ester of D, -N-4-methylbenzoyl-3-aminobutyric acid.
- 99 A method, according to claim 59, wherein the compound is the cyclohexyl ester of the acid D, L-N-benzoyl-3-aminobutyric acid.
- 100. A method, according to claim 59, wherein the compound is the cyclohexyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 101. A method, according to claim 59, wherein the compound is the heptyl ester of D, L-N-4-chlorobenzenesulfonyl-3-aminobutyric acid.
- 102. A method, according to claim 59, wherein the compound is the propyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 103. One method, according to the claim 59, in which the compound is the 2-propenyl ester of D, L-N-benzoyl-3-aminobutyric acid.
- 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-methyldecanoyl ester.
- 106. A method, according to claim 59, wherein the compound is the heptyl ester of D, L-N-3,4-dimethylbenzoyl-3-aminobutyric acid.
- 107. A method, according to claim 59, wherein the compound is 1-methylpentyl ester of D, L-N-4-methylbenzoyl-3-aminobutyric acid.
- 108. A method, according to claim 59, wherein the compound is the methyl ester of D, L-N-2-methylaminobenzoyl-3-aminobutyric acid.
- 109. A method, according to claim 59, wherein the compound is 1-methylpentyl ester of D, L-N-4-chlorobenzenesulfonyl-3-aminobutyric acid.
- 110. A method, according to claim 59, wherein the compound is 3-phenylpropyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 111. A method, according to claim 59, wherein the compound is 1-methyl pentyl ester of D, L-N-2-methylaminobenzoyl-3-aminobutyric acid.
- 112. A method, according to claim 59, wherein the compound is the 3,5-dichlorophenyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 113. A method, according to claim 59, wherein the compound is the 1-methylpentyl ester of the acid D, L-N-4-methylaminobenzoyl-3-aminobutyric acid.
- 114. A method, according to claim 59, wherein the compound is the octyl ester of D, L-N-3,4-dimethylbenzoyl-3-aminobutyric acid.
- 115. A method, according to claim 59, wherein the compound is the octyl ester of D, L-N-2-thiophenecarbonyl-3-aminobutyric acid.
- 116. A method, according to claim 59, wherein the compound is 1-methylpentyl ester of D, L-N-2-thiophenecarbonyl-3-aminoDUriric acid.
- 117. One method, according to the claim 59, in which the harvest is selected from the group consisting of: potatoes, tomatoes, grapes, cereals, melons and cucumbers.
- 118. A method, according to any of claims 59 to 117, wherein the compound is applied to the leaves or stems of the plant.
- 119. A method, according to any of claims 59 to 117, wherein the compound is applied to the roots of plants.
- 120. A method, according to any of claims 59 to 117, wherein the compound is applied to the soil.
- 121. A method, according to any of claims 59 to 117, in which the compound is applied to the seeds, tubers or bulbs of the plants.
- 122. A method, according to any of claims 59 to 117, wherein the compound is applied in the pre-emergence step.
- 123. A method, according to any of claims 59 to 117, wherein the compound is applied in the post-emergence step.
- 124. A method, according to any of claims 59 to 117, wherein the compound is applied to the crop at a dose of 0.1 to 5 kg / ha.
- 125. A method, according to any of claims 59 to 117, wherein the compound is applied at a dose of 0.2 to 2 kg / ha.
- 126. A method for protecting tomatoes or potatoes against early blight or late blight, this method comprises applying to the tomato or potato plants, or to their site, an effective amount of a compound having the formula (I): wherein: a) Ri and R2 are, independently, hydrogen, C? _8 alkyl, phenyl and C? -4 phenylalkyl; b) R3 is straight or branched chain, or cyclic alkyl or alkenyl C? 23; halogenated alkoxyalkyl, alkyl, phenyl or benzyl; alkylphenyl; c) R4 and R5 are hydrogen or C-8 alkyl, where at least one of R4 and R5 is C? _8 alkyl; d) R6 is hydrogen; alkyl C? _8; alkanoyl C2_8; C? -4 phenylalkyl, benzoyl, in which the phenyl part is optionally substituted by one or more halogen atoms or C2-8 alkoxycarbonyl alkyl groups; C0NHR8, wherein R8 is hydrogen, C? _8 alkyl, phenyl, phenylalkyl C? -; phenylalkoxy C -carbonyl, -e) R7 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 its salts.
- 127. A method, according to claim 126, wherein Ri and R2 are, independently, hydrogen, R3 is straight or branched chain, or cyclic alkyl or alkenyl; alkoxyalkyl; halogenated alkyl, phenyl or benzyl; alkylphenyl; R4 and R5 are, independently, hydrogen or C? _3 alkyl; R6 is hydrogen; R7 is benzenesulfonyl or benzoyl, optionally substituted by one or more halogen, 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, R, s and e are hydrogen; R3 is C?-23 straight or branched chain, or cyclic alkyl or alkenyl; alkoxyalkyl; halogenated alkyl, phenyl or benzyl; alkylphenyl or benzyl; R is methyl; and R7 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-benzenesulfonyl-3-amino-N-benzyl-butyramide.
- 130. A method, according to claim 126, wherein the compound is D, L-N-benzenesulfonyl-3-aminobutyranilide.
- 131. A method, according to claim 126, wherein the compound is the n-octyl ester of D, L-N-p-benzoyl-3-aminobutyric acid.
- 132. A method, according to claim 126, wherein the compound is the n-octyl ester of D, L-N-p-methylbenzoyl-3-aminobutyric acid.
- 133. One method, according to the claim 126, in which the compound is sec. -butyl ester of N-p-methylbenzoyl-3-aminobutyric acid.
- 134. A method, according to claim 126, wherein the compound is the n-octyl ester of D, L-N-3,4-dichlorobenzoyl-3-aminobutyric acid.
- 135. A method, according to claim 126, wherein the compound is DL-N-benzoyl-3-aminobutyric acid 2-chloroethyl ester.
- 136. A method, according to claim 126, wherein the compound is N-p-methyl-benzoyl-3-aminobutyric acid 1-methyl-l-pentyl ester.
- 137. A method, according to claim 126, wherein the compound is the n-octyl ester of DL-N-benzenesulfonyl-3-aminobutyric acid.
- 138. A method, according to claim 126, wherein the compound is sec. -butyl ester of N-benzenesulfonyl-3-aminobutyric acid.
- 139. A method, according to claim 126, wherein the compound is N-benzenesulfonyl-3-aminobutyric acid 1-methyl-l-butyl ester.
- 140. One method, according to the claim 126, in which the compound is the heptyl ester of D, L-N-4-methoxybenzoyl-3-aminobutyric acid.
- 141. A method, according to claim 126, wherein the compound is the heptyl ester of D, L-N-3,5-dimethylbenzoyl-3-aminobutyric acid.
- 142. A method, according to claim 126, wherein the compound is the heptyl ester of D, L-N-2,6,6-difluorobenzoyl-3-aminobutyric acid.
- 143. A method, according to claim 126, wherein the compound is the heptyl ester of the acid. D, L- N- -tere. -butylbenzoyl-3-aminobutyric acid.
- 144. A method, according to claim 126, wherein the compound is 1-methylpentyl ester of D, L-N-4-methylbenzenesulfonyl-3-aminobutyric acid.
- 145. A method, according to claim 126, wherein the compound is the 3-phenylpropyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 146. A method, according to claim 126, wherein the compound is D, L-N-4-chlorobenzoyl-3-aminobutyric acid 1-methylpentyl ester.
- 147. One method, according to the claim 126, in which the compound is 2- (trichloromethyl) ethyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 148. A method, according to claim 126, wherein the compound is D, L-N-4-methylbenzenesulfonyl-3-aminobutyric acid 1-methylpropyl ester.
- 149. A method, according to claim 126, wherein the compound is D, L-N-3,4-dimethylbenzoyl-3-aminobutyric acid 1-methylbutyl ester.
- 150. A method, according to claim 126, wherein the compound is the heptyl ester of D, L-N-3-methylbenzoyl-3-aminobutyric acid.
- 151. A method, according to claim 126, wherein the compound is the propyl ester of D, L-N-4-chlorobenzenesulfonyl-3-aminobutyric acid.
- 152. A method, according to claim 126, wherein the compound is 2- (trichloromethyl) ethyl ester of D, L-N-4-methylbvenzoyl-3-aminobutyric acid.
- 153. A method, according to claim 126, wherein the compound is the cyclohexyl ester of D, L-N-4-methylbenzoyl-3-aminobutyric acid.
- 154. One method, according to the claim 126, in which the compound is the cyclohexyl-ester of D, L-N-benzoyl-3-aminobutyric acid.
- 155. A method, according to claim 126, wherein the compound is the cyclohexyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 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 1-methylpentyl ester of D, L-N-2-methylaminobenzoyl-3-aminobutyric acid.
- 159. A method, according to claim 126, wherein the compound is the 3-phenylpropyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 160. A method, according to claim 126, wherein the compound is 1-methylpentyl ester of D, L-N-4-chlorobenzenesulfonyl-3-aminobutyric acid.
- 161. A method, according to any of claims 126 to 160, wherein the compound is applied to the leaves or stems of the plants.
- 162. A method, according to any of claims 126 to 160, wherein the compound is applied to the roots of plants.
- 163. A method, according to any of claims 126 to 160, wherein the compound is applied to the soil.
- 164. A method, according to any of claims 126 to 160, wherein the compound is applied to the seeds.
- 165. A method, according to any of claims 126 to 160, wherein the compound is applied in the post-emergence step.
- 166. A method, according to any of claims 126 to 160, wherein the compound is applied in the pre-emergence step.
- 167. A method, according to any of claims 126 to 160, wherein the compound is applied to the crop at a dose of 0.1 to 5 kg / ha.
- 168. A method, according to any of claims 126 to 160, wherein the compound is applied at a dose of 0.2 to 2 kg / ha.
- 169. A method for protecting cereals against powdery mildew, by applying to the cereal plant, or to its site, a composition containing an effective amount of a compound having the formula (I): wherein: a) Ri and R2 are, independently, hydrogen, C? -8 alkyl, phenyl and C4 phenylalkyl; b) R3 is straight or branched chain, or cyclic alkyl or alkenyl C? -23; halogenated alkoxyalkyl, alkyl, phenyl or benzyl; alkylphenyl; c) R4 and R5 are hydrogen or C? _8 alkyl, where at least one of R4 and R5 is C? _8 alkyl; d) R6 is hydrogen; alkyl C? -8; C2-8 alkanoyl; phenylalkyl C? _4, benzoyl, in which the phenyl part is optionally substituted by one or more halogen atoms or C2.8 alkyl alkoxycarbonyl groups; C0NHR8, wherein R8 is hydrogen, C? _8 alkyl, phenyl, phenylalkyl C? _; C2.4-carbonyl phenylalkoxy; e) R7 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 its salts; and the harvest is selected from tomatoes, potatoes and cereals.
- 170. A method, according to claim 169, wherein Rx and R2 are, independently, hydrogen, R3 is straight or branched chain, or cyclic alkyl or alkenyl; alkoxyalkyl; halogenated alkyl, phenyl or benzyl; alkylphenyl; R4 and R5 are, independently, hydrogen or C? _3 alkyl; R6 is hydrogen; R7 is benzenesulfonyl or benzoyl, optionally substituted by one or more halogen, 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, R2, R5 and Re are hydrogen; R3 is straight or branched chain, or cyclic alkyl or alkenyl C? 23; alkoxyalkyl; halogenated alkyl, phenyl or benzyl; alkylphenyl or benzyl; R4 is methyl; and R7 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-benzenesulfonyl-3-amino-N-benzyl-butyramide.
- 173. A method, according to claim 169, wherein the compound is D, L-N-benzenesulfonyl-3-aminobutyranilide.
- 174. A method, according to claim 169, wherein the compound is DL-N-p-chlorobenzoyl-3-aminobutyric acid 2-chloroethyl ester.
- 175. One method, according to the claim 169, in which the compound is the n-octyl ester of D, L-N-p-methyl-benzoyl-3-aminobutyric acid.
- 176. A method, according to claim 169, wherein the compound is sec. -butyl ester of N-p-methylbenzoyl-3-aminobutyric acid.
- 177. A method, according to claim 169, wherein the compound is the n-octyl ester of D, L-N-3,4-dichlorobenzoyl-3-aminobutyric acid.
- 178. A method, according to claim 169, wherein the compound is the 2-chloroethyl ester of the acid D, L-N-benzoyl-3-aminobutyric acid.
- 179. A method, according to claim 169, wherein the compound is N-p-methylbenzoyl-3-aminobutyric acid 1-methyl-l-pentylester.
- 180. A method according to claim 169, wherein the compound is the n-octyl ester of Dl-N-benzenesulfonyl-3-aminobutyric acid.
- 181. A method according to claim 169, wherein the compound is sec. -butyl ester of N-benzenesulfonyl-3-aminobutyric acid.
- 182. A method according to the claim 169, in which the compound is N-benzenesulfonyl-3-aminobutyric acid 1-methyl-l-butyl-ester.
- 183. A method, according to claim 169, wherein the compound is the heptyl ester of D, L-N-4-methoxybenzoyl-3-aminobutyric acid.
- 184. A method, according to claim 169, wherein the compound is the heptyl ester of D, L-N-3,5-dimethylbenzoyl-3-aminobutyric acid.
- 185. A method, according to claim 169, wherein the compound is the heptyl ester of D, L-N-4-tert. -butylbenzoyl-3-aminobutyric acid.
- 186. A method, according to claim 169, wherein the compound is 1-methylpentyl ester of D, L-N-4-methylbenzenesulfonyl-3-aminobutyric acid.
- 187. A method, according to claim 169, wherein the compound is the heptyl ester of DL, -N-2-methylbenzopyl-3-aminobutyric acid.
- 188. A method, according to claim 169, wherein the compound is the propyl ester of D, L-N-4-chlorobenzenesulfonyl-3-aminobutyric acid.
- 189. One method, according to the claim 169, in which the compound is the cyclohexyl ester of D, L-N-benzoyl-3-aminobutyric acid.
- 190. A method, according to claim 169, wherein the compound is the propyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 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 the 1-methylhexyl ester of the acid D, L-N-4-methylbenzoyl-3-aminobutyric acid.
- 193. A method, according to claim 169, wherein the compound is the D-L-N-4-methylbenzoyl-3-aminobutyric acid 1-methydacanoyl ester.
- 194. A method, according to claim 169, wherein the compound is the N-3, 4-dimethylbenzoyl-3-aminobutyric acid heptyl ester.
- 195. A method, according to claim 169, wherein the compound is the methyl ester of D, L-N-2-methylaminobenzoyl-3-aminobutyric acid.
- 196. One method, according to the claim 169, in which the compound is 1-methylpentyl ester of D, L-N-4-methylbenzoyl-3-aminobutyric acid.
- 197. A method, according to claim 169, wherein the compound is 1-methylpentyl ester of D, L-N-4-chlorobenzenesulfonyl-3-aminobutyric acid.
- 198. A method, according to claim 169, wherein the compound is the methyl ester of D, L-N-4-methylaminobenzoyl-3-aminobutyric acid.
- 199. A method, according to claim 169, wherein the compound is the octyl ester of D, L-N-3, -dimethylbenzoyl-3-aminobutyric acid.
- 200. A method, according to claim 169, wherein the compound is the 3,5-dichlorophenyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 201. A method, according to claim 169 to 200, wherein the compound is applied to the leaves or stems of the plants.
- 202. A method, according to any of claims 169 to 200, wherein the compound is applied to the roots of plants.
- 203. A method, according to any of claims 169 to 200, wherein the compound is applied to the soil.
- 204. A method, according to any of claims 169 to 200, wherein the compound is applied to the seeds, tubers or bulbs of the plants.
- 205. A method, according to any of claims 169 to 200, wherein the compound is applied in the pre-emergence step.
- 206. A method, according to any of claims 169 to 200, wherein the compound is applied in the post-emergence step.
- 207. A method, according to any of claims 169 to 200, wherein the compound is applied to the crop at a dose of 0.1 to 5 kg / ha.
- 208. A method for protecting cucumbers against pubescent downy mildew, by applying to the cucumber plant or its site, a composition containing an effective amount of a compound having the formula (I): wherein: a) Ri and R2 are independently hydrogen, C? -8 alkyl, phenyl and C? -4-phenylalkyl; b) R3 is straight or branched chain, or cyclic alkyl or alkenyl C? -23; halogenated alkoxyalkyl, alkyl, phenyl or benzyl; alkylphenyl; c) ^ and R5 are hydrogen or C? _8 alkyl, where at least one of R4 and R5 is C? -8 alkyl; d) R6 is hydrogen; alkyl C? _8; alkanoyl C2_8; phenylalkyl C? _, benzoyl, in which the phenyl part is optionally substituted by one or more halogen atoms or C2-8 alkoxycarbonyl alkyl groups; C0NHR8, wherein R8 is hydrogen, C? _8 alkyl, phenyl, C? -4 phenylalkyl; C2-4 phenylalkoxycarbonyl; e) R7 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 its salts; and the harvest is selected from tomatoes, potatoes and cereals.
- 209. A method, according to claim 208, wherein Rx and R2 are, independently, hydrogen, R3 is straight or branched chain, or cyclic alkyl or alkenyl; alkoxyalkyl; halogenated alkyl, phenyl or benzyl; alkylphenyl; R4 and Rs are, independently, hydrogen or C? -3 alkyl; R6 is hydrogen; R7 is benzenesulfonyl or benzoyl, optionally substituted by one or more halogen, alkyl groups, amino groups or alkoxy groups; or thiophene-carbonyl; and X is oxygen or -NH.
- 210. A method, according to claim 208, wherein Rx, R2, R5 and R6 are hydrogen; R3 is straight or branched chain, or cyclic, -alkoxyalkyl alkyl or alkenyl; halogenated alkyl, phenyl or benzyl; alkylphenyl or benzyl; R4 is methyl; and R7 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 the propyl ester of D, L-N-4-chlorobenzenesulfonyl-3-aminobutyric acid.
- 212. A method, according to claim 208, in which the compound is 2- (trichloromethyl) ethyl ester of D, L-N-4-methylbenzoyl-3-aminobutyric acid.
- 213. One method, according to the claim 208, in which the compound is the cyclohexyl ester of D, L-N-4-methylbenzoyl-3-aminobutyric acid.
- 214. A method, according to claim 208, wherein the compound is the cyclohexyl ester of D, L-N-benzoyl-3-aminobutyric acid.
- 215. A method, according to claim 208, wherein the compound is the cyclohexyl ester of D, -N-benzenesulfonyl-3-aminobutyric acid.
- 216. A method, according to claim 208, wherein the compound is the heptyl ester of D, L-N-4-chlorobenzenesulfonyl-3-aminobutyric acid.
- 217. A method, according to claim 208, wherein the compound is D, L-N-2-methylaminobenzoyl-3-aminobutyric acid 1-methylpentyl ester.
- 218. A method, according to claims 208 to 217, in which the compound is applied to the leaves or stems of the plants.
- 219. A method, according to any of claims 208 to 217, wherein the compound is applied to the roots of plants.
- 220. A method, according to any of claims 208 to 217, wherein the compound is applied to the soil.
- 221. A method, according to any of claims 208 to 217, wherein the compound is applied to the seeds, tubers or bulbs of the plants.
- 222. A method, according to any of claims 208 to 217, wherein the compound is applied in the pre-emergence step.
- 223. A method, according to any of claims 208 to 217, wherein the compound is applied in the post-emergence step.
- 224. A method, according to any of claims 208 to 217, wherein the compound is applied to the crop at a dose of 0.1 to 5 kg / ha.
- 225. A method, according to any of claims 208 to 217, in which the compound is applied to the crop at a dose of 0.2 to 2 kg / ha.
- 226. A method for protecting the grapes against pubescent downy mildew, by applying to the grape plant, or to its site, a composition containing an effective amount of a compound having the formula (I): wherein: a) Ri and R2 are, independently, hydrogen, Ci-s alkyl, phenyl and phenylalkyl C? _4; b) R3 is straight or branched chain, or cyclic alkyl or alkenyl C? -23; halogenated alkoxyalkyl, alkyl, phenyl or benzyl; alkylphenyl; c) R4 and R5 are hydrogen or C? _8 alkyl, where at least one of R4 and R5 is C? _8 alkyl; d) R6 is hydrogen; alkyl C? _8; C2-8 alkanoyl; phenylalkyl C? -, benzoyl, in which the phenyl part is optionally substituted by one or more halogen atoms or C2_8 alkoxycarbonyl alkyl groups; CONHR8, wherein R8 is hydrogen, C? _8 alkyl, phenyl, phenylalkyl C? -; phenylalkoxy C2_-carbonyl; e) R7 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 its salts; and the harvest is selected from tomatoes, potatoes and cereals.
- 227. A method, according to claim 226, wherein Ri and R2 are, independently, hydrogen, R3 is straight or branched chain, or cyclic alkyl or alkenyl; alkoxyalkyl; halogenated alkyl, phenyl or benzyl; alkylphenyl; R4 and R5 are, independently, hydrogen or C? _3 alkyl; Rs is hydrogen; R7 is benzenesulfonyl or benzoyl, optionally substituted by one or more halogen, alkyl groups, amino groups or alkoxy groups; or thiophene-carbonyl; and X is oxygen or -NH.
- 228. A method, according to claim 226, wherein R1 f R2, R5 and Re are hydrogen; R3 is C1-23 alkyl or alkenyl, straight or branched chain, or cyclic; alkoxyalkyl; halogenated alkyl, phenyl or benzyl; alkylphenyl or benzyl; R4 is methyl; and R7 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 the heptyl ester of D, L-N-2,6,6-difluorobenzoyl-3-aminobutyric acid.
- 230. A method, according to claim 226, wherein the compound is the heptyl ester of D, L-N-4-tert. -butylbenzoyl-3-aminobutyric acid.
- 231. A method, according to claim 226, wherein the compound is 1-methylpentyl ester of D, L-N-4-methylbenzenesulfonyl-3-aminobutyric acid.
- 232. One method, according to the claim 226, in which the compound is the 3-phenylpropyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 233. A method, according to claim 226, wherein the compound is 1-methylpentyl ester of D, L-N-4-chlorobenzoyl-3-aminobutyric acid.
- 2. 34. A method, according to claim 226, in which the compound is 2- (trichloromethyl) ethyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 235. A method, according to claim 226, wherein the compound is D, L-N-4-methylbenzenesulfonyl-3-aminobutyric acid 1-methylpropyl ester.
- 236. A method, according to claim 226, wherein the compound is 1-methylpentyl ester of D, L-N-3,5-dimethylbenzoyl-3-aminobutyric acid.
- 237. A method, according to claim 226, wherein the compound is the heptyl ester of D, L-N-2,6-dichlorobenzoyl-3-aminobutyric acid.
- 238. A method, according to claim 226, wherein the compound is 1-methylpentyl ester of D, L-N-2,6-dichlorobenzoyl-3-aminobutyric acid.
- 239. One method, according to the claim 226, in which the compound is the 3-phenylpropyl ester of D, L-N-4-methylbenzoyl-3-aminobutyric acid.
- 240. A method, according to claim 226, wherein the compound is the 2-chloroethyl ester of D, L-N-3,5-dimethylbenzoyl-3-aminobutyric acid.
- 241. A method, according to claim 226, wherein the compound is the 2-chloroethyl ester of D, L-N-4-methoxybenzoyl-3-aminobutyric acid.
- 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, in which the compound is the heptyl ester of D, L-N-4-chlorobenzoyl-3-aminobutyric acid.
- 244. A method, according to claim 226, wherein the compound is the L-metril-2-methoxyethyl-ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 245. A method, according to claim 226, wherein the compound is the 3-phenylpropyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 246. A method, according to claims 226 to 245, in which the compound is applied to the leaves or stems of the plants.
- 247. A method, according to any of claims 226 to 245, wherein the compound is applied to the roots of the plants.
- 248. A method, according to any of claims 226 to 245, in which the compound is applied to the soil.
- 249. A method, according to any of claims 226 to 245, in which the compound is applied to the seeds, tubers or bulbs of the plants.
- 250. A method, according to any of claims 226 to 245, wherein the compound is applied in the pre-emergence step.
- 251. A method, according to any of claims 226 to 245, wherein the compound is applied in the post-emergence stage.
- 252. A method, according to any of claims 226 to 217, in which the compound is applied to the harvest at a dose of 0.1 to 5 kg / ha.
- 253. A method, according to any of claims 226 to 245, in which the compound is applied to the crop at a dose of 0.2 to 2 kg / ha.
- 254. A method for protecting melons against downy mildew, by applying to the grape plant, or to its site, a composition containing an effective amount of a compound having the formula (I): in which a) Ri and R2 are independently hydrogen, C? -8 alkyl, phenyl and phenylalkyl? 4; b) R3 is straight or branched chain, or cyclic C3-C3 alkyl or alkenyl; halogenated alkoxyalkyl, alkyl, phenyl or benzyl; alkylphenyl; c) R4 and Rs are hydrogen or C? -8 alkyl, where at least one of R and Rs is C? -8 alkyl; d) R6 is hydrogen; alkyl C? _8; C2-s alkanoyl; C? -4 phenylalkyl, benzoyl, wherein the phenyl part is optionally substituted by one or more halogen atoms or C2_8 alkoxycarbonyl alkyl groups; C0NHR8, wherein R8 is hydrogen, CX-8 alkyl, phenyl, phenylalkyl C? _; C2-4 phenylalkoxycarbonyl; e) R7 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 its salts; and the harvest is selected from tomatoes, potatoes and cereals.
- 255. A method, according to claim 254, wherein Rx and R2 are, independently, hydrogen, R3 is straight or branched chain, or cyclic alkyl or alkenyl; alkoxyalkyl; halogenated alkyl, phenyl or benzyl; alkylphenyl; R and R5 are independently, hydrogen or C? -3 alkyl; R6 is hydrogen; R7 is benzenesulfonyl or benzoyl, optionally substituted by one or more halogen, alkyl groups, amino groups or alkoxy groups; or thiophene-carbonyl; and X is oxygen or -NH.
- 256. A method, according to claim 254, wherein Ri, R2, Rs and Re are hydrogen; R3 is C?-23 straight or branched chain, or cyclic alkyl or alkenyl; alkoxyalkyl; halogenated alkyl, phenyl or benzyl; alkylphenyl or benzyl; R4 is methyl; and R7 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 254, wherein the compound is the heptyl ester of D, L-N-4-methoxybenzoyl-3-aminobutyric acid.
- 258. A method, according to claim 254, wherein the compound is the heptyl ester of D, L-N-4-tert. -butylbenzoyl-3-aminobutyric acid.
- 259. A method, according to claim 254, wherein the compound is the 3-phenylpropyl ester of D, L-benzenesulfonyl-3-aminobutyric acid.
- 260- A method, according to claim 254, wherein the compound is 1-methylpentyl ester of D, L-N-4-chlorobenzoyl-3-aminobutyric acid.
- 261. A method, according to claim 254, wherein the compound is D-, L-N-benzenesulfonyl-3-aminobutyric acid 2- (trichloromethyl) ethyl ester.
- 262. One method, according to the claim 254, in which the compound is the heptyl ester of D, L-N-3-methylbenzoyl-3-aminobutyric acid.
- 263. A method, according to claim 254, wherein the compound is 1-methylpentyl ester of D, L-N-3,5-dimethylbenzoyl-3-aminobutyric acid.
- 264. A method, according to claim 254, wherein the compound is 1-methylpentyl ester of D, L-N-2,6-dichlorobenzoyl-3-aminobutyric acid.
- 265. A method, according to claim 254, wherein the compound is the D-L-N-3,5-dichlorobenzoyl-3-aminobutyric acid 2-chloroethyl ester.
- 266. A method, according to claim 254, wherein the compound is D-, L-N-benzoyl-3-aminobutyric acid 2- (trichloromethyl) ethyl ester.
- 267. A method, according to claim 254, wherein the compound is the heptyl ester of D, L-N-2-methylbenzoyl-3-aminobutyric acid.
- 268. A method, according to claim 254, wherein the compound is the D, L-N-4-methylbenzenesulfonyl-3-aminobutyric acid 2-bromoethyl ester.
- 269. One method, according to the claim 254, in which the compound is the heptyl ester of D, L-N-4-methylbenzenesulfonyl-3-aminobutyric acid.
- 270. A method, according to claim 254, wherein the compound is the 3-phenylpropyl ester of D, L-N-benzenesulfonyl-3-aminobutyric acid.
- 271. A method, according to claims 254 to 270, wherein the compound is applied to the leaves or stems of the plants.
- 272. A method, according to any of claims 254 to 270, wherein the compound is applied to the roots of plants.
- 273. A method, according to any of claims 254 to 270, wherein the compound is applied to the soil.
- 274. A method, according to any of claims 254 to 270, wherein the compound is applied to the seeds, tubers or bulbs of the plants.
- 275. A method, according to any of claims 254 to 279, wherein the compound is applied in the pre-emergence step.
- 276. A method, according to any of claims 254 to 270, wherein the compound is applied in the post-emergence step.
- 277. A method, according to any of claims 254 to 270, wherein the compound is applied to the crop at a dose of 0.1 to 5 kg / ha.
- 278. A method, according to any of claims 254 to 270, wherein the compound is applied to the crop at a dose of 0.2 to 2 kg / ha.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL119908 | 1996-12-25 | ||
| IL122435 | 1997-12-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA99006009A true MXPA99006009A (en) | 2000-05-01 |
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