MXPA99009675A - Use of hydroxylamine derivatives, and method and preparations for increasing the tolerance of field crops against weather stresses - Google Patents

Abstract

This invention relates to the use of hydroxylamine derivatives of general formula (I), wherein R1 represents phenyl, N-heteroaryl, S-heteroaryl or a naphthyl group which may be substituted, an unsubstituted or substituted phenylamino or alkylamino or lower alkoxy;X represents halo, amino or an unsubstituted or substituted phenylamino group, or amino substituted with one or two lower alkyl or a hydroxy group;Y represents hydrogen, hydroxy or acyloxy, or if Y represents hydroxy, the molecule may contain a dioxazine ring closed at the carbon atom carrying the X group formed by formal XH elimination;R2 and R3, independently from each other, represent hydrogen or lower alkyl group;R2 and R3 along with the adjacent nitrogen atom form a 5- to 7-membered saturated hetero ring, to increase the tolerance of cultivated plants against weather condition stresses, such as cold, frost and drought.

Description

USE PE DERIVATIVES OF HYDROXYLAMINE. AND METHOD AND PREPARATIONS FOR I NCREMENTING THE TOLERANCE OF CROPS FIELD AGAINST TENSION IS AMBI ENTALES TECHNICAL FIELD ICO This invention relates to the use of hydroxylamine derivatives of the general formula (I), wherein R 1 represents phenyl, N-heteroaryl, S-heteroaryl, or a naphthyl group which may be substituted with one or more halo, alkyl , alkoxy, haloalkyl or nitro, an unsubstituted or substituted phenylamino or alkylamino or lower alkoxy, X represents halo, preferably chlorine or bromine, amino or an unsubstituted or substituted phenylamino group, or amino substituted with one or two lower alkyls or a hydroxy group provided that if R1 represents unsubstituted phenylamino, alkylamino or lower alkoxy or substituted, then X may not represent halo, Y represents hydrogen, hydroxy or acyloxy, preferably longer alkanoyloxy, or if Y represents hydroxy, the molecule may contain a dioxazine ring closed at the carbon atom carrying the group X formed by the formal elimination of XH, R2 and R3, independently of each other, represent hydrogen or lower alkyl group provided that R2 and R3 may not represent hydrogen simultaneously, R2 and R3 together with the adjacent nitrogen atom form a saturated 5- to 7-membered hetero ring, and the method and preparation for increasing the tolerance of cultivated plants against stresses of the environmental condition ICA TECHNIQUE BACKGROUND Damage to plants grown for environmental stress, such as cold, frost and drought, causes significant losses for agriculture. These factors, within this invention briefly referred to as environmental stresses, can occur at any period of growth or vegetation of the plant. Although they affect plants in various ways and plants react to them differently according to species and type, the effect is usually connected to the water metabolism of plants. The protection of plants against environmental stresses is made more difficult by the widely varied distribution of time, strength and length of these tensions present in most agricultural regions. In the present invention a temperature is considered cold if it is lower than the minimum temperature necessary for the normal physiological functioning of individuals belonging to a given species or plant type, but greater than the freezing point of water. Generally its effect may not be determined immediately by simple observation. The damage caused by the cold appears later, after heating, such as the decrease in growth of the plant, the withering or loss of color (chlorosis), or in the most severe cases, death of the plant. The frost, that is, the temperature below 0 degrees Celsius does not necessarily cause the plant to die. After it has finished, the plant can be regenerated, but the irreversible cell damage caused by the frost will press its development, which will decrease its yield at the end. While cold and frost usually appear at an early stage of plant development and hence damage the plant in germination or development, drought damages the fully developed plant and endangers the later stage of development. Decreasing the level of evaporation of the plant can give the reduction of losses. For example, there is a method when the surface of the plant is coated with a polymer film in order to physically limit the transpiration of the plant in the case of drought. For this purpose, the polyethoxylated polyoxypropylene polymers described in U.S. Patent No. 4,828,602 are applied. The disadvantage of the method is that it requires a local application of the coating material, which can be done only by investing a large amount of manual labor. An inhibition of durable perspiration is not desirable in any way; system-effect transpiration inhibitors are more favorable with respect to the plant's physiology. Thorough research related to the effects of environmental stresses on plants has been carried out to reduce damage from cold, frost and drought, and a large number of scientific publications deal with the plant's physiological relevance of cold tolerance, frost and droughts Since plants react to these environmental stresses very differently according to their botanical characteristics, a theoretically satisfactory explanation of tolerance to cold, frost and drought has not yet been given, and hence the methods developed for application in the practice to improve the tolerance of plants against environmental stresses are very diverse.

For example, it is known in the art that growth-regulating materials, which are compounds of hormonal activity, affect the tolerance of plants to cold, frost and drought positively, and therefore are applied to the treatment of cultivated plants. A typical example is abscisic acid, which is a growth-regulating hormone. Abscisic acid by itself is difficult to synthesize and hence it is not applied in agriculture. However, materials analogous to abscisic acid chemically and in their effects are used, which have an identical or stronger effect than abscisic acid itself, especially when combined with other compounds, which ensures a synergistic increase in effect. For example, PCT publication WO No. 9,608,481 A1 discloses that plants are treated with epoxycyclohexane derivatives to make their development and performance more favorable and to increase their tolerance against cold and drought. In addition to these compounds, brassidosteroids are also used as synergistic aids. EP No. 327 309 A1 discloses a compound containing a poly-substituted cyclohexenyl-acetylene derivative as an effective agent, and a phenyl-benzyl-urea derivative variously and multi-substituted as a synergistic auxiliary. With the help of this substance of hormonal activity, the tolerance of the plant against drought can be improved. The compounds of hormonal activity are undoubtedly significant, because they have an intense effect when applied in a small amount, however, their disadvantage is that they affect the metabolic processes that take place in plants to a considerable degree, modify the balance hormone from plants, which can result in unpredictable physiological changes. Therefore, such compounds and products must be applied with care in practice. Before application, it is essential to carry out preliminary experiments related to a given species or type of plant in order to determine the suitability and optimal circumstances of application of the product in a given agricultural region, which limits its use in agricultural practice. To avoid the aforementioned disadvantages of substances of hormonal activity, researchers have turned to more simple, hormonally indifferent substances to find a suitable effective agent to improve the tolerance of plants against cold, frost and drought. According to PCT publication WO No. 92 / 08,350 A1, tetrahydrofurfuryl alcohol, tetrahydrofurfuryl amine, or the combination of these compounds is used to improve the tolerance of plants against cold. These effective agents lack the mentioned disadvantages of substances with hormonal activity, their production is easier, and hence they are more economical, but in view of the practice they are not favorable. This is due, according to the aforementioned document, to that it is recommended to spray the plants more than once with the solution of the effective agent in order to achieve a satisfactory degree of regeneration of the plants affected by the cold, and repeat the treatment after the cold has disappeared, but the most convenient way is to spray the plants regularly. An entire surface treatment is considered important to ensure contact of the effective agent on the entire surface of the plant. Therefore, thorough or repeated spraying is recommended. This requirement can be met only by investing a large amount of manual labor. According to Hungarian Patent No. 181, 241, secondary or tertiary β-hydroxyethyl-amines or respective ammonium quaternary salts, preferably 2-hydroxy-ethyl-amines and trimethyl-β-hydroxy-ethyl-ammonium chloride may be applied. (Choline chloride) and, in certain cases, combinations of these to improve the tolerance of plants against cold and frost. Primarily, the effective agent is applied to the plant by spray. It can be concluded from the experimental section of the patent that the effective agent aims to change the phospholipid composition of the membrane of plant cells, and thus the fluidity of the membrane. Hence, the effective agents mentioned can be applied for the treatment of fully developed plants only. This was also supported by the experimental results. The treatment of seedbeds and seeds, which is mentioned in the patent may be ineffective with these effective agents since the plants lack the necessary membrane parts. An exception is choline chloride, whose application for seed treatment is known from publication J P No. 62 161 701. In this case, however, the regulating effect of the overall growth of the substance is used, as described in the aforementioned document, and this effect causes among others the improved tolerance of the plant sprouting against the cold. However, the growth regulating hormone activity substances have all the disadvantages described above. To summarize the above, we can conclude that several different attempts have been published in the patent literature with the purpose of improving the tolerance of cultivated plants against environmental stresses. The agents and effective products of these Patents are, however, suitable for direct agricultural application only with the mentioned limiting conditions. Our research had the purpose of finding effective agents, which increase the tolerance of the plants to the cold, frosts and droughts, but they are hormonally neutral, non-toxic, being the limits of their application the smallest possible, and which are adequate not only for the treatment of fully developed plants but also for seedbeds and seeds.

DESCRIPTION OF THE INVENTION It was found that the hydroxylamine derivatives of the general formula (I), wherein R 1 represents phenyl, N-heteroaryl, S-heteroaryl, or a naphthyl group which may be substituted with one or more halo, alkyl , alkoxy, haloalkyl or nitro, an unsubstituted or substituted phenylamino or alkylamino or lower alkoxy, X represents halo, preferably chlorine or bromine, amino or an unsubstituted or substituted phenylamino group, or amino substituted with one or two lower alkyls or a hydroxy group provided that if R1 represents unsubstituted or substituted phenylamino, alkylamino or lower alkoxy, then X may not represent halo, Y represents hydrogen, hydroxy or acyloxy, preferably longer alkanoyloxy, or if Y represents hydroxy, the molecule may contain a dioxazine ring closed at the carbon atom carrying the group X formed by the formal elimination of XH, R2 and R3, independently of each other, represent hydrogen og lower alkyl moiety provided that R2 and R3 may not represent hydrogen simultaneously, R2 and R3 together with the adjacent nitrogen atom form a 5- to 7-membered saturated hetero ring, show the required effect and satisfy the above requirements. These compounds act in an inductive manner, that is, they increase the level of resistance if the plant faces environmental stresses, such as when the environmental stresses mentioned above affect the plant. Induced metabolic processes result in improved tolerance against cold, frost and drought. Based on this observation, this invention relates to the use of hydroxylamine derivatives of the general formula (I), wherein R1, X, Y, R2, and R3 are as above, for the improvement of the tolerance of plants grown against environmental tensions. In the general formula (I), a lower alkyl group preferably contains 1-6 carbon atoms, most preferably 1-4 carbon atoms, and a lower alkoxy group contains 1-6, preferably 1-4 carbon atoms. . In compounds of the general formula (I), wherein R 1 is a phenyl or substituted phenylamino group, the alkyl groups attached to the phenyl ring as substituents are preferably lower alkyl groups of 1-6 carbon atoms. The alkoxy substituents of the phenyl ring preferably contain 1-6 carbon atoms. The haloalkyl substituents of the phenyl ring preferably contain alkyl, most preferably C alquilo .6 alkyl. The most preferable haloalkyl substituent is the trifluoromethyl group. If R 1 represents alkylamino, it preferably contains at most 12 carbon atoms. If R 1 represents N-heteroaryl, it is preferably pyridyl or pyrazinyl group, while if R 1 represents an S-heteroaryl group, it is preferably thienyl. Finally, if Y represents a long-chain alkanoyloxy of carbons, it preferably contains 12-20 carbon atoms. Some of the hydroxylamine derivatives of the general formula (I) are known compounds. Those compounds of the general formula (I) in which R 1 represents phenyl or pyridyl or naphthyl which can be substituted with halo or alkoxy, X represents amino and Y represents hydroxy, are known from Hungarian Patent No. 177,578, which also describes the process of preparation of these compounds, as well as the different possibilities for synthesis. These compounds, as selective beta-blocking agents, can be applied in the therapy of angiopathy, mainly diabetic angiopathy. Those compounds of the general formula (I), in which R 1 represents phenyl or alkoxyphenyl or pyridyl or naphthyl, X represents ryalo and Y is hydroxy, as well as their preparation are known from Hungarian Patent No. 207,988. These compounds can also be applied in the therapy of angiopathy. Those compounds of the general formula (I), in which R 1 represents naphthyl or haloalkylphenyl, X is hydroxy and Y represents hydroxy, are known from published Hungarian Patent Application No. 2385/92. These compounds have an anti-ischemic and antianginal effect, and can be applied here in particular in the therapy of cardiac diseases. Those compounds of the general formula (I), wherein R 1 represents phenyl or phenyl group substituted by the substituents listed above or a pyridyl group, X represents halo and Y is a hydrogen atom, are known from the PCT publication WO No. 95/30649 A1. The same document describes the preparation of these compounds. These compounds have an anti-ischemic effect and hence can be applied in the therapy of diabetic angiopathy. In addition, those compounds of general formula (I) are also known, in which R 1 represents phenylamino which is unsubstituted or substituted by alkyl, alkoxy, halo, haloalkyl or nitro, or an alkoxy or alkylamino group, X represents hydroxy and And it is hydrogen, hydroxy or alkanoyloxy. Its description can be found in PCT publication WO 97/00251, which describes the preparation of these compounds as well. These compounds have anti-ischemic effect and hence they can be applied in the therapy of diseases of heart and blood vessels. Note that in the known compounds R2 and R3 represent the same as defined above, and therefore these two substituents are not described in detail. It should also be noted that in certain compounds of the general formula (I), tautomerism may occur, ie they may appear in a tautomeric structure different from but corresponding to the formula (I).

In particular, this is the case when compounds of the general formula (I) contain a hydroxy group such as X, where the tautomeric version containing a part of the molecule - (CO) -N H- that does not appear in the structural formula is more stable. The remaining compounds of the general formula (I) form the subject matter of our pending patent application. New compounds are those hydroxylamine derivatives of the general formula (I), in which X represents halo Y is hydroxy, and R 1 represents a group that is different from those described in the aforementioned Hungarian Patent No. 207,988 dealing with these types of compounds, for example phenyl substituted with alkyl, haloalkyl or nitro. These substances are prepared analogously to the cited description by diazotizing the corresponding compound containing an N-H 2 group at the X-site. The necessary starting amino compounds are also produced by known method, by the coupling reaction of the amidoxime. and a derivative of 3-amino-2-propanol, for example according to the method described in Hungarian Patent No. 177, 578. The N-substituted amidoximes of the general formula (I), wherein R 1 represents an aromatic group and X represents a substituted amino group, are also novel compounds, and can be produced by the coupling reaction of a suitable imidoyl halide of the general formula (1), wherein Hal represents a halo and R1 is as before, while R 'is the substituent of the amino group of X, and a derivative of 1-amino-3-aminooxy-propane of the general formula (2), wherein R2, R3 and Y are as before. The reactions must be carried out in a neutral solvent, for example in chlorinated hydrocarbon, at room temperature and after separation by extraction, the product is isolated as a salt with an organic or inorganic acid. Other novel compounds of the general formula (I) are N-hydroxy-guanidine derivatives in which both R1 and X are substituted nitrogen atoms. These derivatives are produced by acylation of a suitable aminooxy compound of the general formula (2), if the acylating agent is haloformamidine of the general formula (3), where Hal represents halogen, R1 is as before, and R 'and R "are substituents of the amino group that appear as X in the product The reaction is carried out in a two-phase system, in the mixture of some organic solvent not miscible with water and an aqueous base, preferably aqueous sodium carbonate solution. it is isolated in this case by extraction by extraction as well and, if possible by salt formation, any of those new compounds of the general formula (I), in which Y represents acyloxy, can be produced by O-acylation of the corresponding compound containing hydroxy as Y. The starting compounds are either known from the literature mentioned above or can be produced according to the described method. n use acid halides, active esters or other usual reagents applicable for O-acylation. The reactions can be carried out in a neutral solvent, usually at room temperature and if necessary in the presence of a suitable acid-binding agent, such as an organic or inorganic base, for example triethylamine or solid sodium carbonate. For acylating agent, acid chlorides are preferable, where the compound itself can behave as an acid-binding agent, and hence the product can usually be easily isolated in the hydrochloride form by ethereal crystallization after evaporation. When less reactive acylating agents are used, the Schotten-Baumann acylation can also be applied. The products are generally isolated in the form of their salts with an organic or inorganic acid. With respect to the application of the invention, the most preferable compounds were the following of the general formula (I): N- [2-hydroxy-3- (1-piperidinyl) propoxy] -benzinidoyl-chloride hydrochloride (Compound 1) N- [2-Hydroxy-3- (1,1-dimethylethyl-amino) propoxy] -3-trifluoromethyl-benzamide monohydrochloride (Compound 2) N- [2-palmitoyloxy-3- (1 -) monohydrochloride p -peridinyl) propoxy] -3-pyridinecarboximidamide (Compound 3) N- [3- (1-piperidinyl) propoxy] -3-nitro-benzimidoyl-chloride monohydrochloride (Compound 4) N- [2-hydroxy-3-monohydrochloride] - (1-piperidinyl) propoxy] -2-nitro-benzimidoyl-chloride (Compound 5) N - [[3- (1,1-dimethylethyl) -amino]] - 2-hydroxypropoxy] -N'-phenyl- hydrochloride Benzamidine (Compound 6) N-N'-dimethyl-N'-phenyl-N "- [3- (1-piperidinyl) propoxy] -guanidine hydrochloride (Compound 7) N- [3- (1-p) N -hydrochloride peridinyl) propoxy] -pyrazinecarboximidoyl chloride (Compound 8) 3- (3-pyridyl) -5-diethylaminomethyl-5,6-dihydro-1,2,4-dioxazine hydrochloride (Compound 9) N- [2- hydroxy-3- (1-piperidinyl) propoxy] -1-naphthalenecarboxamide (Compound 10) N- [2-hydroxy-3- (1-piperidinyl) propoxy] -ethylurethane (Compound 11) N-hexyl-N'- [2-hydroxy-3- (1-pipe ridinyl) propoxy] -urea (Compound 12) N, N-dimethyl-N'-phenyl-N "- [2-hydroxy-3- (1-piperidinyl) propoxy] -guanidine hydrochloride (Compound 13) N- N-hydrochloride [3- (1-piperidinyl) propoxy] -thiophene-2-carboxymethylchloride (Compound 14) N - [3- (1-piperidinyl) propoxy] -N'-phenyl-benzamidine hydrochloride (Compound 15) The compounds of the general formula (I) are favorable with respect to the application in the cultivation of plants because they are suitable for treating the fully developed plant and the seed or the stock. These compounds can be applied to plants using any of the usual methods widely used in plant protection.

Based on the foregoing, the invention relates to a method for increasing the tolerance of cultivated plants against environmental stresses. According to the invention, the plant or its protected seed is treated with a hydroxylamine derivative of the general formula (1), wherein R1, X, Y, R2 and R3 are as above. Preferably, an aqueous solution of the compound of the general formula (I) is used for the treatment, but alternatively a preparation containing the usual carriers and the hydroxylamine derivative of the general formula (I) can be applied as an effective agent. The dose and concentration of the effective agent of the general formula (I) is dependent on the species or type of protected plant and the method of application. If the process according to the invention is directed to improve the tolerance of the plant against cold and frost, preferably the seed of the plant should be treated with a hydroxylamine derivative of the general formula (I), where R1, X, And, R2 and R3 are as before. The seed of the plant should be covered with the appropriate product containing the active ingredient and suitable for coating, preferably pearled, in certain cases dressed, or the aqueous solution of the effective agent can be used simply. The preferred method is to soak the seed of the plant in an aqueous solution of a compound of the general formula (I). For this purpose an aqueous solution with 1-200 mg / l of concentration of the compound of the general formula (I) is prepared.

The process according to the invention can be carried out by coating the seed of the plant with a solution containing a hydroxylamine derivative of the general formula (I). The compounds of the general formula (I) can be combined with fillers in certain cases. For the coating of the seeds, pearling agents are preferably applied, which contain compounds of the general formula (I) in a concentration of 0.1-10 g / l together with the customary pearling and auxiliary materials. Pearlizing agents may contain other effective agents in addition to the effective agent also mentioned, such as fungicides or additives that promote germination, for example microelements. The pearling agent is applied in a small volume. For example, when bean, soy or corn seeds are treated, only 1 ml or a lesser amount of pearling agent is used for 100 seeds, which is dried on the seeds uniformly while draining constantly. Furthermore, this invention relates to a method for improving the tolerance of plants grown against the cold, where the plant is sprayed before or at the time when the cold season arrives with a spray preparation containing a hydroxylamine derivative of the formula general (I) as an effective agent. The spraying is carried out with an aqueous solution of 1 -500 mg / liter of concentration of the effective agent, which may occasionally contain auxiliary spraying materials, such as surface active materials (detergent). In certain cases, the compounds of the general formula (I) can be combined and sprayed to the plants to be protected with other effective agents such as fungicides. Spraying is going to be done at the beginning of the dangerous period in terms of cold temperature. If more than one period is to be taken into consideration, then the plants should be sprayed at the beginning of each of these periods. According to the invention, to improve the tolerance of cultivated plants the plant must be sprayed before or at the time when the dry season arrives with a spray preparation containing a hydroxylamine derivative of the general formula (1) as the effective agent. The spraying is carried out using an aqueous solution of 1 -500 mg / l of active agent. The plants to be protected are sprayed before or at the beginning of the period when there is a risk of drought. In each case, the characteristics of the given species or plant type determines the applicable amount of the active agent. If more than one period of drought is to be taken into account, then the spraying must be repeated at the beginning of each of these periods. For the treatments listed above, a simple aqueous solution of the hydroxylamine derivatives of the general formula (I) is used, but preferably such preparations which contain appropriate auxilliary materials in addition to the active agent, to improve spraying, distribution and absorption of the active agent. The composition of the invention for improving the tolerance of plants grown against environmental stresses contains 0.001 -95 m / m% hydroxylamine derivative of the general formula (I), in which R1, X, Y, R2 and R3 are as above , in addition to solid or liquid carriers and possible auxiliary materials suitable for agricultural application. The composition preferably contains water as a liquid vehicle agent. The aqueous solution of the active agent is a concentrate, which must be diluted before application in order to prepare the appropriate concentration mentioned above. Preferably, the aqueous solution contains surfactants, those solutions for treating the seed contain filler and pearlizing auxiliary materials, such as film-forming materials. Sprays contain an agent that improves adhesion, a substance to improve spraying, light-protecting agent, if required, a stabilizing agent and other additives in addition to detergents. For spraying purposes, ULV concentrates, emulsifiable concentrates, hydrophilic, granular or soluble micro-granules dilutable with water can be applied. These products contain anionic or non-anionic detergents in order to help the dissolution with water. The solid products may contain kaolin, diatomite or dolomite as a vehicle, but may also contain any other solid carrier agent widely applied in such products. Preferably, pearlite is used as a carrier agent for the production of microgranulate. The compositions of the invention can be combined or applied simultaneously with other pesticides, if the active agent of the latter is compatible with the active agent of the composition of the invention. In these cases the spraying of the composition of the invention does not require a separate process, it can be carried out together with the usual pesticide treatment of the cultivated plants.

THE BEST WAY TO CARRY OUT THE INVENTION The invention is demonstrated by the following examples without limiting the scope of the invention.

EXAMPLE 1 N- [2-Palmitoyloxy-3- (1-piperidinyl) propoxy] -3-pyridinecarboximidamide monohydrochloride (Compound 3) 14.7 g (52.8 mmol) of N- [2-hydroxy-3- (1 -) are dissolved. piperidinyl) propoxy] -3-pyridine-carboximidamide in 160 ml of chloroform. 7.7 ml (55 mmol) of triethylamine are added, followed by the dropwise addition of a solution of palmitoyl chloride (14.7 g, 56.5 mmol) in 85 ml of chloroform. The mixture is stirred overnight at room temperature. The next day, an additional 3.8 ml of triethylamine and 7.4 g of palmitoyl chloride are added, and stirring is continued for a further day. Then the solution is extracted with water, 5 V / V% acetic acid and water, successively, it is dried over anhydrous sodium sulfate, and evaporated to dryness. The residue (28.2 g of oil) is dissolved in ethyl acetate, and the product is precipitated by the addition of 30 ml of 1 N HCl / ethyl acetate. The thick, white precipitate is filtered, washed with ethyl acetate and dried. Yield: 10.9 g (37%) P.f. : 1 10-1 13 ° C EXAMPLE 2 N- [2-Hydroxy-3- (1-piperidinyl) propoxy-2'-nitro-benzene-carboximidoyl chloride monohydrochloride (compound 5) 6.0 g (16.7 mmol) of N- [2-hydroxy] monohydrochloride is dissolved. -3- (1-piperidinyl) propoxyl-2'-nitro-benzene-carboximidamide in 21 ml of water, then add 48 ml of concentrated hydrochloric acid. The solution is cooled to -5 ° C, then a cold solution of 2.1 g (33.3 mmol) of sodium nitrite in 9 ml of water is added dropwise. During the whole reaction the internal temperature is maintained at 0 ° C. When the addition is complete, the mixture is stirred for an additional 4 hours and cooled overnight. The product is filtered, washed with cold water and dried. Yield: 3.9 g (63%) Pm: 159-162 ° C IR (KBr): 3298, 2983, 2932, 2746, 1593, 1574, 1535, 1445, 1391, 1354, 1317, 1288, 1242, 1198, 1117, 1092, 1069, 1020, 968, 947, 914, 852, 793, 756, 708, 577 c? Tf1 Example 3 N - [[3- (1,1-dimethylethyl) -amino] -2-hydroxypropoxy] -N'-phenyl-benzamidine hydrochloride (Compound 6) 4 g (24.7 mmol) of benzanilide-imide chloride are dissolved in 45 ml of chloroform. Then 5.32 g (24.7 mmol) of 1-amino-oxy-3 - [(1,1-dimethyl] -amino] -2-hydroxypropane dissolved in 45 ml of chloroform are added dropwise to the resulting solution. The reaction mixture is stirred at room temperature for 3 hours, and then washed with ml of 1 M aqueous sodium carbonate solution. The chloroform phase is dried with sodium sulfate, filtered and evaporated. The residue of the evaporation is crystallized with hexane. The resulting base is dissolved in 50 ml (5.33 g) of ethyl acetate and then 3.35 ml of 3.67 N hydrochloric acid / ethyl acetate are added. The isolated crystals are filtered, washed with ethyl acetate and dried. Yield: 2.97 g (72%) P.f. : 140-143 ° C NMR-H 1 (solvent: CDCl 3, reference: CDCl 3 [ppm]: 9.7 (m, 1 H) and 8.1 (m, 1 H, N H 2 +), 7.8 (s, 1 H, N HO ), 6.7-7.4 (m, 10 H, 2 x Ph), 5.7 (d, 1 H, OH), 4.5 (m, 1 H, CH), 4.25 (d, 2 H, OCH2), 3.1 (m, 2 H, NCH2); 1.25 (s, 9 H, lBu).

Example 4 N- N '-dimethyl-' -f-N "- [3- (1-piperidinyl) propoxy] -guanidine hydrochloride (Compound 7) 20 ml of 1 M aqueous sodium carbonate solution was added to 1 040 g (6.5 mmol) of 1-amino-3- (1-piperidinyl) propane dissolved in 10 ml of ether While stirring intensively, 1.200 ml (6.5 mmol) of N, N-dimethyl-N are added. '-phenyl-chloroformamidine dissolved in 10 ml of ether.After 2 hours of stirring, an additional 20 mg (0.1 mmol) of N, N-dimethyl-N'-phenyl-chloroformamide was added, after an additional 3 hours of stirring, the phases are separated and the ether phase is dried with sodium sulfate, filtered and evaporated The residue (1.700 mg of yellow oil) is dissolved in 10 ml of ethyl acetate. . 5 ml of 0.54 M hydrochloric acid / ethyl acetate, and then the product is cooled and the isolated crystals are filtered. The crude product is crystallized from a methanol-ether mixture to give 847 mg of white crystalline material. Yield: 847 mg (38%) Mp: 138-139 ° C (methanol-ether) NMR-H (solvent: CDCl 3, reference: CDCl 3 [ppm]): 7.2 (t, 2 H, Ph-m); 7. 1 (d, 2 H, Ph-o); 6.9 (t, 1 H, Ph-p); 6.6 (m, 1 H, NH +); 4.0 (t, 2 H, OCH2); 3.5 (m, 2 H); 3.0 (t, 2 H, CH2); 2.6 (s, 6 H, 2xNCH3); 2.2-2.5 (m, 6 H, 3xNCH2); 1.8 (m, 4 H) and 1.3 (m, 2 H, piperidine). The product crystallized from isopropanol melts at 213-216 ° C Example 5 N- [3- (1-piperidinyl) propoxy] -N'-phenyl-benzamidine hydrochloride (Compound 15) 0.8 g (5 mmol) of 1-amino-3- (1-piperidinyl) propane are dissolved in 7.5 my chloroform 1.08 g (5 mmol) of benzanilide-imide chloride dissolved in 7.5 ml of chloroform are added dropwise, and then the reaction mixture is stirred for 3 hours. It is then washed with 10 times 10 ml of water, and the chloroform phase is dried with sodium sulfate, filtered and evaporated. The residue of the evaporation is dissolved in 20 ml of 2N aqueous sodium hydroxide solution and the solution is extracted with 20 ml of ethyl acetate. The ethyl acetate phase is dried with sodium sulfate and filtered, and then 0.8 ml of 3.45 M hydrochloric acid / ethyl acetate are added. The isolated precipitate is filtered and dried. Yield: 0.8 g (46%) P.f. 164-166 ° C (crystallized from ethyl acetate) NMR-C13 (solvent: CDCl 3, reference: CDCl 3 [ppm]): 157.55 (C-amidine); 135. 75 (N-Ph-ipso); 132.84 (N-Ph-ipso); 128.95 (N-Ph-m); 128.84 (N-Ph-m); 126.66 (N-Ph-p); 125.34 (N-Ph-p); 124.0 (C-Ph-p); 74.02 (OCH2); 54. 20 (NCH2); 53.30 (2.6 piperidine); 23. 19 (CH2); 22.63 (3.5 piperidine); 21 .76 (4 piperidine).

Example 6 N, N-Dimethyl-N'-phenyl-N "- [2-hydroxy-3- (1-piperidinyl) propoxy] -guanidine hydrochloride (Compound 13) 1. 150 mg (6.58 mmol) are dissolved of 1-amino-oxy-2-hydroxy-3- (1-piperidinyl) -propane] in 20 ml of ether and to this solution are added 20 ml of 1 M sodium carbonate solution, then 1, 206 mg ( 6.58 mmol) of N, N-dimethyl-N'-phenyl-chloroformamydine dissolved in 10 ml of ether.After two hours, 22 mg (0.1 1 mmol) of N are also added to the reaction mixture. N-dimethyl-N? -phenyl-chloroformamidine After stirring for a further 3 hours, the layers are separated, the ether layer is dried with sodium sulfate, filtered and evaporated.The remaining 1, 800 mg of yellow oil They are taken in 10 ml of ethyl acetate, and to this solution 10.46 ml of 0.54 M HCl / ethyl acetate are added, cooled and the yellow crystals are separated by filtration.The impurities are removed by crystallizing first in acetone, then in ethyl acetate. ethyl. 674 mg (28%) pale yellow powder MP: 127-129 ° C (ethyl acetate) NMR-H1 (solvent: CDCl3; Reference: CDCl 3 [ppm]): 7.1 -7.4 (m, 5 H, Ph); 5.9 (m, 1 H, OH); 4.6 (m, 1 H, CH); 4.1 (m, 2 H, OCH2); 3.6 (m, 4 H, 2-6 piperidine); 3.4 (m, 2 H,); 3.2 (m, 1 H, N H); 1.8 (m, 4 H, 3-5 piperidine); 1.4 (m, 2 H, 4-piperidine).

EXAMPLE 7 Increased tolerance to freezing by seed treatment In this experiment the tolerance of corn, soybean and pepper seeds treated with the active agent against cold was tested. This test imposed temperature stress and oxygen deficiency in the seeds and was carried out according to Barla-Szabó and Dolinka CSVT (Complex Stressing Vigour Test). For a simple test, 200 seeds were soaked for 48 hours at 25 ° C and another 48 hours at 5 ° C in 150 ml of distilled water containing the active agent at a concentration of 10 mg / l. Following 96 hours of soaking, the seeds were subsequently germinated between moist paper rolled for 96 hours at 25 ° C. There were 25 seeds in each roll, the rolls were placed vertically in containers and covered with a plastic bag in order to to reduce evaporation. During the entire procedure the seeds were kept in the dark.

At the end of the experiment, the number of seeds developed normally and without germination was recorded. The length of the almacigo plants was measured and the average length of the 5 longest almacigo plants was calculated. The almacigo plants longer than 0.33 times the average length of the five largest almacigo plants were considered to be of high vigor, and the seeds of almacigo of low vigor were shorter than this length. In experiments with corn, it was found that the tested active agents do not influence the germination and development of the germinated Ma 17 inbred corn line under optimal circumstances, at 25 ° C. Under the circumstances of the CSVT test, however, they proved to be effective , as shown in Table 1. Table 1 Active agent List of plants with high vigor (%) Compound 1 38 * Compound 2 29 * Compound 9 33 * Compound 1 1 24 Compound 3 47 * Compound 12 23 * Compound 4 28 * Compound 5 32 * Compound 6 35 * Compound 7 36 * Control 19 The results marked with * are significant compared to the control, if P < 0.05. Using the same experimental method for inbred corn line compounds HMv09, shown in Table 2, they proved to be effective, significantly increasing the ratio of high vigor plants. Table 2 Active agent List of plants with high vigor (%) Compound 2 49 * Compound 10 52 * Compound 4 40 * Compound 6 57 * Compound 13 56 * Compound 14 45 * Compound 15 53 * Control 33 The results marked with * are significant compared to the control, if P < 0.05.

In the case of an additional experiment with corn populations with low tolerance to cold (LT) and high tolerance to cold (HT) [Ref: P. Landi, E. Frasearon, A. Lovato; EUPHYTICA 64 21 -29 (1992)], the following positive effects were found (Table 3).

Table 3 Active agent List of plants with high vigor (%) HT LT Compound 2 98 * 94 * Compound 3 92 * 86 * Compound 4 94 * 88 * Compound 5 96 * 92 * Control 84 74 The results marked with * are significant compared to the control, if P < 0.05. Experiments with McCall soybeans also showed that the active agents have no effect on the germination and development of the plants under normal conditions. When the CSVT test was applied, the following results were obtained (Table 4).

Table 4 Active agent List of plants with high vigor (%) Compound 2 43 * Compound 4 46 * Compound 8 47 * Control 38 The results marked with * are significant compared to the control, yes.

It was further observed that Compound 8 decreased the number of non-germinated seeds by 50% (control: 33%, treated: 17%, significant at P <0.05). Experiments with green peppers showed similarly that the active agents have no effect under normal circumstances, do not influence the germination of the seeds and the development of the plants kept at 25 ° C. Under the circumstances of the CSVT test, they increased the length of sprouts and roots along with the proportion of high vigor almacigo plants. The ratio of ungerminated seeds decreased by 30% on average due to treatment with active agents. The results are shown in Table 5. Table 5 Active agent List of plants with high vigor (%) Compound 2 47 * Compound 4 45 * Control 36 The results marked with * are significant compared to the control, if P < 0.05. In order to make the results more comprehensible, it should be noted that the CSVT procedure is developed to predict the minimum expected ratio of seeds sprouted under environmental stresses. In a given set of seeds, the proportion of those seeds that emerge safely and germinate properly in cold spring weather is 90% for seeds that proved to be of high vigor in the CSVT test, while the proportion of those seeds that sprouted Safely and germinated properly in cold spring weather is only 60% for seeds that proved to be of low vigor in the test. Hence,, if an active agent improves the vigor of the almacigo plants, in the end it improves the shoot ratio under open field conditions in the case of colder than optimum ground temperature. The above experiments prove that the compounds of the general formula (I) are capable of improving the vigor of the plants or seeds of the almacigo and therefore improve the opportunity of sprouting, if unexpected weather stresses occur after sowing.

EXAMPLE 8 Pearl bean bean seed bean seeds Soybean seeds are treated with a pearling agent, which contains 1 mg / ml of N- [3- (1-piperidinyl) propoxy] -3-nitro-monohydrochloride. Benzimidoyl-Coryuro (Compound 4) in a 5% aqueous solution of polyvinyl alcohol. A glass container with 100 seeds and 1 ml of pearling agent was filled and while the vessel was turned, the seeds were coated with the agent and then allowed to dry. For seeds treated in this manner, we obtained the following results when placed under the conditions of the CSVT test described in Example 7.

Table 6 Treatment Ratio of plants with high vigor (%) untreated root shoot control 47 40 pearled with PVA 52 49 pearled with PVA and 63 * 58 * Compound 4 The results marked with * are significant compared to the control, if P < 0.05.

The PVA slightly increased the proportion of high vigor plants. The PVA solution containing Compound 4 proved to be such a pearling agent that it was able to increase the proportion of high vigor plants significantly under the experimental conditions, increasing the length of both the suckers and the roots. In a further CSVT experiment using also McCall soybeans, polyvinyl alcohol (PVA) was applied to seed pearls. The 2.5 mg doses of the active agents were dissolved in 1 ml of 2.5% PVA solution, and this amount was applied to 100 pieces of seeds. The improvement of cold tolerance is observed by the significant lengthening of the germ and roots. The results are shown in Table 7.

Table 7 Active agent Relative length (control = 100) root germ Compound 2 106 128 Compound 9 1 10 131 Compound 3 133 150 Compound 5 1 16 135 Compound 6 127 152 The experiments clearly show that, according to the results of the vigor test, the chances of sprouting of the plants increased after pearling with the active agent.

Example 9 Increase in bean drought tolerance Based on the experiences of our preliminary experiments, the plants hardened before the application of the active agent; holding the water for a few days, until the first signs of wilting appeared. Then the plants were watered and the active agent was either dissolved in the water or sprayed directly to the plants. Then, the plants were subjected to different periods of drought according to the given experiment, they were irrigated again, and after a regeneration period of one week, the survival rate was determined. a) Seaway bean culture was hardened for 5 days retaining the water. Then the plants were watered for 2 days normally. During this time, a solution with 10 mg / liter and 100 mg / liter concentration of active agent was applied, twice a day dissolved in water or by direct spraying. After the water was retained for 7 days, and after a regeneration period of 1 week, the survival rate was determined. The results are summarized in Table 8.

Table 8 Active agent Irrigated (10mg / l) Irrigated (100mg / i) Spray (100mg / l) Survival (%) Control 17 17 0 Compound 2 30 * 41 * 71 * Compound 6 25 * 36 * The results marked with * are significant compared to the control, if P < 0.05. b) in this experiment, soybean plants (cv. Seaway) were hardened for 7 days instead of the 5 days described in part a. Then a solution of 10 mg / liter and 100 mg / liter concentration of active agent was applied twice a day for 2 days. Then they followed 7 days without water, and after a regeneration period of 1 week, the experiment results were evaluated. The results are summarized in Table 9.

Table 9 Active agent Survival (%) Compound 2 14 * Compound 4 39 * Control 0 The results marked with * are significant compared to the control, if P < 0.05.

Example 10 Increase in drought tolerance of soybean Soy beans of soybeans were hardened cv. Blylyi 44 for 6 days by retaining water. This was followed by 2 days of watering, and the active agent was applied in the water. The concentration of the active agent solution was 50 mg / liter. After suspending irrigation for 4 days and a regeneration period of 1 week, the number of surviving plants was recorded. The results are listed in Table 10.

Table 10 Active agent Survival (%) Compound 2 25 * Compound 4 33 * Control 18 The results marked with * are significant compared to the control, if P < 0.05.

Water was stopped for 10 days for a certain group of plants in the experiment. It was observed that almost all the plants died. Each of the 4 surviving plants had been previously treated with the active agent.

Example 1 1 Increase in tolerance to bean freezing Seeds of bean seed store cv. Seaway under normal conditions for the first 2 weeks, then treated with solutions of 10 mg / liter and 100 mg / liter concentration of the active agents examined 2 and 1 days before the start of the freeze tolerance experiments. In the experiment, the plants were kept at -2 ° C for 8 hours, then they grew under normal conditions for 1 week, and the survival ratio was determined. Four trays were used for each experiment and 6 seeds were planted in each tray. The compounds in Table 1 1, significantly increased the survival rate.

Table 1 1 Active agent Treatment Survival (%) Compound 2 sprayed, 100mg / l 40 * Control sprayed 25 Compound 2 irrigated, 10mg / l 25 * Compound 4 irrigated, 10mg / l 40 * Control irrigated 18 The results marked with * are significant compared to the control, if P < 0.05.

Example 12 Increase in cold tolerance of corn in a gradient chamber The experiment was carried out using the inbred line of corn Mo 17. The seeds were coated with a 2% solution of the examined compound dissolved in 2 ml of polyvinyl alcohol before germination, where the amount of the above solution was applied to 100 seeds. The seeds germinated for 3 days on moist filter paper, then sown and cultured in a gradient chamber for 6 weeks. In the gradient chamber, the temperature was maintained at a spacing between 18 and 12 ° C, with differences of 1 ° C. This was followed by a 1-week regeneration at a temperature of 23/20 ° C. In the experiment, measured the length of the plants 16, 31 and 43 days after sowing, and at the end of the experiment the fresh weight of the plants was measured. The experiment was carried out in 4 plants for each temperature and by each treatment. The results demonstrate the potential for increased germination of the maize inbred line examined, and the improvement of the early development of seeds and plants of almacigo compared with the control without treatment. The experimental results are summarized in Table 12.

Table 12 Increase the tolerance to cold I of corn in the gradient chamber with compounds 2, 5 and 6 Control Compui this Compound Compu Temp. Long time. FW Long. FW Long. FW Long. FW (days) (cm) (g) (cm) (9) (cm) (g) (cm) (g) 18 ° C 16 12.9 __ 13.2 __ 15.0 14.6 __ 31 22.0 - 28.4 - 28.4 - 25.0 - 43 35.0 5.3 37.0 6.0 38.0 6.2 39.0 7.6 17 ° C 16 13.1 _ », 17.0 _._ 19.7 __ 17.8 __ 31 22.9 - 27.7 - 31 .2 - 29.9 - 43 36.0 4.8 36.5 5.5 37.3 6.6 44.3 9.7 16 ° C 16 10.2 __ 15.2 «_ 15.4 12.4 31 20.6 - 24.8 - 26.8 - 26.4 - 43 33.1 4.2 32.3 4.5 34.5 5.0 42.3 7.7 ° C 16 9.2 -, _ 10.0 __ 10.2 9.5 31 15.0 - 17.7 - 21 .3 - 22.2 - 43 21 .2 2.0 28.5 3.6 32.3 4.4 34.0 5.4 14 ° C 16 5.2".. 7.6" _ 9.7 _ "5.8 __ 31 10.8 - 15.4 - 17.2 - 1 1.6 - 43 20.3 1 .6 25.9 2.7 25.1 2.9 20.3 1 .3 13 ° C 16 5.0 6.0 7.4 - 4.7 ~ 31 10.8 1 0.1 13.1 10.0 - 43 17.2 1 .0 16.0 23.8 2.1 18.5 1 .1 12 ° C 16 5.4 5.0 5.8 4.5 - 31 8.7 7.9 1 1 .3 - 10.9 - 43 17.8 0.9 18.9 1 .2 20.1 1 .5 25.5 2.0 In the following examples, results of field experiments are shown, which were arranged with early seeding in order to determine the effect of the hydroxylamine derivatives of the invention on the development and yield of the plants in this case under natural conditions.

Example 13 Increase in yield of field soybean crop The experiment was carried out using soybean cv. Blylyi 44. Before planting, the seeds were treated with Rhyzobium japonicum nitrogen-fixing bacteria, which form a root nodule that provides 50-70% of the plant's nitrogen demand. The examined compounds were applied by pearling to the seeds; 1 ml of pearlizing agent containing 1 mg of active agent in an aqueous solution of 5% PVA for 100 seeds was used. The plants were planted after land preparation in the fall, using a crop rotation system, 3-5 cm deep in the soil, with a row spacing of 45-50 cm, a distance between plants of 5 cm and a density of 450,000-500,000 plants / ha. The sowing date was April 15, 1997. During the development of the plant, the usual cultivation procedures were followed and the usual pesticides were used. The harvest took place in September-October, with the water content of the grains being between 16-18%. The results are listed in Table 13.

Table 13 Active agent Weight of harvest Improvement compared to (kg / m2) control (%) Control 0.45 Compound 6 0.52 15.5 Compound 5 0.50 1 1.1 Compound 2 0.55 22.2 Example 14 Increase in maize yield in field culture The experiments were carried out on lines Mo 17 and AMO 406. Before planting, the seeds were covered with fungicides, insecticides and agents for rodent control, and, at the same time, the tested compounds were applied in the form of a 2.5 mg / ml solution concentration in a 2% PVA solution; 2 ml of solution for 100 seeds were used. The plants were planted after the preparation of the soil in the autumn, using a crop rotation system, 4-8 cm deep in the soil, with a distance of 45 cm rows, a distance between plants of 30 cm and a density of 60,000-80,000 plants / ha. The sowing date was April 15, 1997. During the development of the plant, the usual cultivation procedures were followed, and the usual pesticides were applied. The harvest took place when the water content of the grains decreased below 28%. In the harvest, the weight of the plants and the crop were determined. The results are listed in Tables 14 and 15.

Table 14 Active agent Harvest weight (kg / m2) Relationship with the control (Compound No.) Control 1 ° 1 .55 100% 0.09 100% 2 ° 1.42 100% 0.088 100% 6 1 ° 2.03 130.9% 0.101 1 12.2% 2 ° 2.0 140.8% 0.1 1 125% 1 ° 1 .97 127% 0.109 121 .1% 2 ° 0.093 105.6% 2 1 ° 1.85 1 19.3% 0.108 120% 2 ° 2.0 140.8% 0.1 1 1 126.1% Table 15 Field cultivation of the corn line AMO 406 Active agent Harvest weight (kg / m2) Relationship to control (Compound No.) Control 1 ° 1 .65 100% 0.097 100% 2 ° 1.13 100% 0.075 100% 6 1 ° 2.2 133.3% 0.115 118.5% 2 ° 1.75 154.8% 0.097 129.3% 1 ° 1.8 109% 0.1 103.0% 2 ° 1.8 159.2% 0.1 133.3% 1 ° 2.35 140.6% 0.16 164.9% 2 ° 1.25 110.6% 0.089 118.6% EXAMPLE 15 Leaf dew Leaf dew is prepared with the following composition (proportions by weight): Compound 2 20 Sodium lauryl sulfate 3 Sodium lignin sulfonate 6 Water 63 Kaolin 8 Example 16 Leaf dew Leaf dew is prepared with the following composition (proportions by weight): Compound 4 Alkyl aryl sulfonate Water 75 Example 17 Pearl agent The pearlizing agent is prepared with the following composition (weight proportions): Compound 3 0.25 Aqueous solution of 2% polyvinyl alcohol 9.75 The pearling agent must be applied as an active agent in an amount of 0.01-0.02 m / m% with respect to the weight of the seed.

Example 18 Granulate The granulate is prepared with the following composition (proportions by weight): Compound 13 10 Limestone powder 64 Ethylene glycol 3 High dispersion silicic acid 4 Sodium lignin-sulfate 4 Water 15 The mixture of the components must be ground in a hammer mill until it reaches the particle size of 5 microns.

Example 19 Preparation of powder The powder preparation is prepared with the following composition (weight proportions): Compound 6 Polyvinyl pyrrolidone 10 Silicon dioxide 25 Chinese clay (kaolin) 15 Example 20 Powder preparation The powder preparation is prepared with the following composition (weight proportions): Compound 1 Sodium l-gnin-sulfonate 5 Isopropyl naphthalene sulfonate 1 Silicon dioxide 4 Charge (kaolin) 40

Claims (16)

1. REVIVAL NAMES 1. The use of hydroxylamine derivatives of the general formula (I), wherein R 1 represents phenyl, N-heteroaryl, S-heteroaryl, or a naphthyl group which may be substituted with one or more halo, alkyl, alkoxy , haloalkyl or nitro, an unsubstituted or substituted phenylamino or alkylamino or lower alkoxy, X represents halo, preferably chlorine or bromine, amino or an unsubstituted or substituted phenylamino group, or amino substituted with one or two lower alkyls or a hydroxy group provided that if R represents unsubstituted or substituted phenylamino, alkylamino or lower alkoxy, then X may not represent halo, Y represents hydrogen, hydroxy or acyloxy, preferably longer alkanoyloxy, or if Y represents hydroxy, the molecule may contain a ring of dioxazine closed at the carbon atom carrying the group X formed by the formal elimination of XH, R2 and R3, independently of each other, represent hydrogen or lower alkyl group or whenever R2 and R3 may not represent hydrogen simultaneously, R2 and R3 together with the adjacent nitrogen atom form a saturated 5- to 7-membered hetero ring, to increase the tolerance of cultivated plants against stresses of the weather condition.
2. 2. Method for increasing the tolerance of cultivated plants against stresses of the climate condition, which comprises treating the plant or its seed with a hydroxylamine derivative of the general formula (I), wherein R1, R2, R3, X and Y they are as in claim 1.
3. 3. Method for increasing the tolerance of plants grown against cold and frost, which comprises treating the seed with a compound of the general formula (I), wherein R1, R2, R3, X and Y are as in claim 1.
4. 4. Method according to claim 3, which comprises treating the seed of the plant with the aqueous solution of a hydroxylamine derivative of the general formula (I), wherein R1, R2, R3, X and Y are as in claim 1
5. 5. Method according to claim 4, comprising soaking the seed of the plant in the aqueous solution of a hydroxylamine derivative of the general formula (I), wherein R1, R2, R3, X and Y are as in the claim 1
6. 6. Method according to claim 3, comprising coating the seed of the plant with a product containing a hydroxylamine derivative of the general formula (I), wherein R \ R2, R3, X and Y are as in the claim 1 and optionally other active agents and / or auxiliary materials for germination improvement as well.
7. 7. Method for increasing the tolerance of plants grown against the cold, which comprises spraying the plant with a solution containing a hydroxylamine derivative of the general formula (I), wherein R1, R2, R3, X and Y are as in claim 1 as active agent, before or when the cold season is established.
8. 8. Method for increasing the tolerance of plants cultivated against drought, which comprises spraying the plant with a solution containing a hydroxylamine derivative of the general formula (I), wherein R1, R2, R3, X and Y are as in claim 1 as an active agent, before or when the drought period is established.
9. 9. Composition for increasing the tolerance of plants cultivated against stresses to the climate, comprising as an abject ingredient a hydroxylamine derivative of the general formula (I), wherein R 1 represents phenyl, N-heteroaryl, S-heteroaryl, or a naphthyl group which can be substituted with one or more halo, alkyl, alkoxy, haloalkyl or nitro, X represents an unsubstituted or substituted phenylamino group, or amino substituted with one or two lower alkyl, and represents hydrogen, hydroxy or acyloxy, preferably longer alkanoyloxy, or if Y represents hydroxy, the molecule may contain a closed dioxaztine ring at the carbon atom bearing the X group formed by the formal removal of XH, R2 and R3, independently of each other, represent hydrogen or lower alkyl group provided that R2 and R3 may not represent hydrogen simultaneously, R2 and R3 together with the adjacent nitrogen atom form a saturated hetero ring of 5 to 7 members.
10. The composition of claim 9 which also comprises solid or liquid carriers and optionally auxiliary materials suitable for agricultural use. eleven .
11. The composition according to claim 9 wherein R1 is unsubstituted or substituted phenyl, X is unsubstituted or substituted phenylamino and R2, R3 and Y are as defined in claim 1.
12. 12. The composition according to claim 1 which comprises N- hydrochloride. { [3- (1,1-dimethyl-ethyl) -amino] -2-hydroxy-propoxy} -N'-phenyl-benzamidine as active compound.
13. 13. The composition according to claim 1 comprising N- [3- (1-piperidinyl) propoxy] -N'-phenyl-benzamidine hydrochloride as the active ingredient.
14. 14. Hydroxylamine derivatives of the general formula (I), wherein R 1 is phenyl which is unsubstituted or substituted with one or more selected from halo, alkyl, alkoxy, haloalkyl and nitro, X is unsubstituted or substituted phenylamino, and is hydrogen, hydroxy or acyloxy, preferably longer alkanoyloxy, R2 and R3, independently of each other, are H or lower alkyl provided that at least one of them is not hydrogen, or R2 and R3 together with the nitrogen adjacent thereto , they form a saturated hetero ring of 5 to 7 members, and their salts.
15. 15. N- Hydrochloride. { [3- (1,1-dimethyl-ethyl) -amino] -2-hydroxy-propoxy} -N'-phenyl-benzamidine.
16. 16. N- [3- (1-piperidinyl) propoxy] -N'-phenyl-benzamidine hydrochloride.