The method of obtaining derivatives nitroguanidine

 

(57) Abstract:

The present invention relates to a method for producing compounds of formula (I) by hydrolysis of the compounds of formula (II). The method differs in that the reaction is carried out at a pH value of 8-12. This method allows to obtain the compounds of formula (1) with higher purity and higher yield. 6 C. p. F.-ly, 2 PL.

The present invention relates to a method for obtaining compounds of formula I

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in which

R1denotes hydrogen or C1-C4alkyl,

R2denotes hydrogen, C1-C6alkyl, C3-C6cycloalkyl or residue-CH2IN,

And denotes unsubstituted or, depending on the possibilities of substitution of the cyclic system, ranging from one to fivefold substituted by substituents selected from the group comprising halogen, C1-C3alkyl, C1-C3alkoxy, halogen-C1-C3alkyl, C1-C3halogenoalkane, cyclopropyl, halogenlampen,2-C3alkenyl,2-C3quinil,2-C3halogenoalkanes and C2-C3halogenoalkanes,

WITH1-C3alkylthio,1-C3allogenicity, allelochemics, monocyclic or bicyclic heterocyclic residue and

In denotes phenyl, 3-pyridyl or thiazolyl, under certain conditions, depending on the possibilities of substitution of the cyclic system, substituted with one to three substituents from the group comprising C1-C3alkyl, C1-C3halogenated, cyclopropyl, halogenlampen,2-C3alkenyl,2-C3quinil, C1-C3alkoxy, C2-C3halogenoalkanes,2-C3halogenoalkanes,1-C3halogenoalkane,1-C3alkylthio,1-C3allogenicity, allyloxy, propargyloxy, allylthio, propargite, halogenations, halogenierte, halogen, cyano and nitro,

and under certain conditions it is possible E/Z-isomers, mixtures of E/Z-isomers and/or tautomers, in free form or in the form of salts carried out by hydrolysis of the compounds of formula II

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in which R1, R2and a have the same meaning as indicated for formula I, a3denotes unsubstituted or substituted C1-C10alkyl, C3-C6cycloalkyl, phenyl or benzyl. This method differs in that the above reaction is carried out at sacrilegous two isomeric forms

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In accordance with this under the compounds of the formula I below refers to the corresponding E/Z-isomers, even if not particularly specified in each case.

The compounds of formula I may be partially provided in the form of tautomers, for example, according to the following forms

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In accordance with these compounds under formula I above and in the following refers to the corresponding tautomers, even if not particularly specified in each case.

The compounds of formula I, as well as their possible E/Z isomers and tautomers, can be represented in the form of salts. The compounds of formula I having at least one basic centre can form, for example, an acid additive salt. Such salts are formed, for example, with strong inorganic acids, in particular mineral acids, such as sulfuric acid, phosphoric acid or a halogen acid, with strong organic carboxylic acids, such as optionally substituted, for example, halogen, C1-C4alcancarao acid, for example acetic acid, such as optionally unsaturated dicarboxylic acids, for example oxalic, malonic, Malaya, malic, tartaric or citric acid, or benzoic acid, or with organic sulfonic acids, such as optionally substituted, for example, halogen, C1-C4alcamovia or arylsulfonate, for example methane-or p-toluensulfonate. Salts of compounds of formula I with acids of the specified type receive preferably with appropriate processing of reaction mixtures.

Further, the compounds of formula I contain at least one acidic group can form salts with bases. As such salts with bases include, for example, metal salts, in particular salts of alkali and alkaline earth metals, for example salts of sodium, potassium or magnesium salts, or salts formed with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, with mono-, di -, or three(ness.)alkylamine, for example ethyl-, diethyl-, triethyl - or dimethylpropylene, or with mono-, di - or trihydroxy(ness.)alkylamino, for example mono-, di - or triethanolamine. In addition, under certain conditions, can be formed corresponding internal salts. Preferred in accordance with the invention, acceptable in the chemistry of salt. Above and beyond under the concept of adnie the compounds of formula I. Said equally applies to E/Z isomers and tautomers of compounds of formula I and their salts. Preferred is a free form.

Used in the definitions of the substituents of formulas I and II some General concepts have the following specific values.

Considered as a possible Vice-halogen atoms are fluorine and chlorine, and bromine and iodine, preferably fluorine, chlorine and bromine, and especially chlorine. By halogen is meant either an independent Deputy, or assistant, as it takes place in halogenoalkane, allogeneically, halogenoalkane, halogennitroalkane, halogenoalkanes, halogenoalkane, halogenations or halogenierte. Acceptable as substituents alkyl, alkylthio-, alkeline, alkyline and CNS remains can be remotemachine or branched. As examples of such Akilov can be named, among others, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl. As appropriate CNS residues are among the other such as methoxy, ethoxy, propoxy, isopropoxy or butoxy and their isomers. Alkylthio is soy Vice-alkyl, CNS, alkeline, alkyline or cycloalkyl group substituted with halogen, they may be gorodilova only partially, or completely. For halogen, alkyl and alkoxygroup fair values above. Examples of alkyl fragments of these groups are from one - to three-fold substituted by fluorine, chlorine and/or bromine, methyl, such as, for example, F2or CF3; from one - to five-fold substituted by fluorine, chlorine and/or bromine, ethyl, as, for example, CH2CF3, CF2CF3, CF2Cl3, CF2CHCl2, CF2F2, CF2FCl3, CF2ADHD2, CF2CHClF, CF2BrF or CClFCHClF; from one - to seven-substituted by fluorine, chlorine and/or bromine propyl or isopropyl, as, for example, CH2Snugs2Br, CF2FF3CH2CF2CF3or CH(CF3)2; from one - to nine-fold substituted by fluorine, chlorine and/or bromine butyl or one of its isomers, such as CF(CF3)FF3or CH2(CF2)2CF3; 2-chlorocyclopropane or 2,2-diversicolor; 2,2-defermined, 2,2-dichlorovinyl, 2-chlorallyl, 2,3-dichlorovinyl or 2,3-dibromovinyl.

In the case of substitution of the named alkyl, alkenes the same or different substituents from among the above. Preferably in the presence of substituted groups one or two substituents. Consider as Vice cycloalkyl residues include, among other things, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Alkeneamine and alkyline groups contain unsaturated carbon-carbon bond. Typical representatives of such groups are allyl, methallyl or propargyl, as well as vinyl and ethinyl. Double or triple bond in allyloxy, propargyloxy, allylthio - or proprietorof separated from the junction with the heteroatom (O or S) is preferably a saturated carbon atom.

It is already known that to obtain a 1,3-disubstituted 2-nitroguanidine in one-deputizing 2-nitroguanidine you can enter another Deputy (for example, by alkylation) (see , for example, European application EP 0375907, 0376279 and 0383091). Because of the presence in used to carry out these reactions as a source of material one-deputizing 2-nitroguanidine three reactive hydrogen atoms proposed up to the present time substitution reactions of this type often proceeded selectivity and led to the formation of undesirable products of substitution. In the above-mentioned European is different microestimation with primary amines in the removal of mercaptan. However, obtaining offered for use in the known methods as starting compounds nitrosotoluene compounds containing leaving ancilliary associated with considerable difficulties.

Further, in EP-A 0483062 describes a method of obtaining compounds of formula I, where hydrolyzing the compound of the above formula II. According to the examples presented in this publication, the hydrolysis should be carried out in acidic conditions. Any examples, confirming the possibility of hydrolysis in basic conditions, in this publication, are completely absent.

Thus, it can be stated that the above-described methods for producing compounds of formula I do not meet the requirements regarding the purity and yield of products, and this necessitates the development of more sophisticated methods of obtaining these compounds from produced simple by starting compounds.

Unexpectedly, it was found that proposed in the present invention method satisfies these requirements.

The method of hydrolysis according to the invention is carried out at a pH value of 8-12, primarily 8-10 and also preferably 7-10, under normal davino carried out in an inert towards the components of the solvent or diluent. As solvents are particularly suitable alcohols, such as methanol, ethanol, propanol and isopropanol, and in some cases water. Other usable for this purpose solvents are, for example, ethers such as tetrahydrofuran and dioxane, as well as other solvents that do not have a negative impact on the reaction. All solvents can also be used in the form of their mixtures. Preferably hydrolyzing the compound of formula II in aqueous medium or in a mixture of water and alcohol. As the basis for implementing the method according to the invention is suitable preferably hydroxides of alkali and alkaline earth metals, such as NaOH and KOH; carbonates, such as PA2CO3, Panso3TO2CO3; phosphates, such as Na3PO4, Na2HPO4; alcoholate, such as methanolate sodium, ethanolate sodium, and potassium tert-butanolate; organic amines, such as morpholine, piperidine, pyrrolidine, mono -, di -, or three(NISS. )alkylamine, for example ethyl-, diethyl-, triethyl or dimethylpropylene, or mono-, di - or trihydroxy(ness.)alkylamine, for example mono-, di - or triethanolamine, or dialkylanilines, as, for example, N,N-dimethyl - or N,N-diethylaniline, as well as with the EU ETS, as, for example, buffer solutions of acetates or phosphates.

Proposed in the invention method is preferably for producing compounds of formula I, where the heterocyclic residue And is unsaturated and is linked as a link cycle through the carbon atom with the main part. Particularly preferred residues And include pyridyl, thiazolyl, tetrahydrofuranyl, dihydrofurane, furanyl, N-oxidability, oxazolyl, isoxazolyl, thienyl, morpholinyl, piperidinyl, pyridinyl and pyrazinyl; first of all, pyridyl, thiazolyl, tetrahydrofuranyl and N-oxidability, especially 3-pyridyl, 2-halogenase-5-yl, 2,3-dehalogenase-5-yl, 2-halogentated-5-yl, tetrahydrofuran-3-yl, 5-methyltetrahydrofuran-3-yl, 1-occupied-3-yl, 1-oxo-2-halogenase-5-yl and 1-oxo-2,3-dehalogenase-5-yl.

It is also preferred heterocycles And carry from one to three substituents from the group comprising halogen, C1-C3alkyl, C1-C3halogenated and C1-C3halogenoalkane, each containing respectively 1 to 7 halogen atoms, and C1-C3alkoxy.

It is preferably obtained according to the invention the compounds of formula I are further those, in which the balance In prostatecomy from the group including halogen, C1-C3alkyl, C1-C3halogenated, and C1-C3halogenoalkane, each containing respectively 1 to 7 halogen atoms, and C1-C3alkoxy.

Among obtained according to the invention compounds of formula I should be allocated such that R1denotes hydrogen, R2denotes hydrogen, methyl, ethyl or cyclopropyl, and A denotes a pyridyl, 1-oxopyridine, tetrahydrofuranyl, thiazolyl or pyridyl, 1-oxidability, tetrahydrofuranyl or thiazolyl, substituted respectively with one to three substituents from the group comprising halogen, C1-C3alkyl, C1-C3halogenated and1-C3halogenoalkane, each containing respectively 1 to 7 halogen atoms, and C1-C3alkoxy. In this respect, the interest is also the compounds of formula I, in which

a) R1denotes hydrogen;

b) R2denotes hydrogen, C1-C3alkyl or cyclopropyl and especially methyl;

C) And means 2-chloropyrid-5-yl, tetrahydrofuran-3-yl, 5-methyltetrahydrofuran-3-yl or 2-chlorothiazole-5-yl;

g) R3stands WITH1-C3alkyl, cyclopropyl, cyclohexyl ered halogen, WITH1-C4alkyl, halogen-C1-C4alkyl, nitro, C1-C4alkoxy and halogen-(C1-C4alkoxy.

Obtained according to the invention the compounds of formula I along with good compatibility in warm-blooded animals, fish and plants are valuable active substances for pest control. First of all the compounds of formula I can be used for controlling insects and arachnids, which are pests of useful and ornamental plants in agriculture, especially in cotton, vegetable and fruit growing, forestry, to protect stocks and materials, as well as for the purposes of veterinary services, primarily to protect domestic and useful animals. The compounds of formula I effective in the first place when they are applied against sucking insect pests of plants and primarily against aphids (Aphiden) and cicadas. With pesticide action of substituted 2-nitroguanidine of the same type as that obtained according to the present invention, are described, for example, in European application EP 376279, 375907 and 383091.

Used in the method according to the invention of the parent compound, respectively, the initial products of the formula II, partially known or can Ei this is primarily about the compounds of formula IIA

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in which

R1, R2and R3have the meanings specified for formula I,

R4denotes halogen, C1-C3alkyl, C1-C3alkoxy, halogen-(C1-C3alkyl, C1-C3halogenoalkane, cyclopropyl, halogenlampen,2-C3alkenyl,2-C3quinil,2-C3halogenoalkanes and C2-C3halogenoalkanes,1-C3alkylthio,1-C3allogenicity, allyloxy, propargyloxy, allylthio, propargite, halogenations, halogenierte, cyan and nitro, preferably C1-C3alkyl,

n denotes 0, 1, 2 or 3, preferably 0 or 1,

and under certain conditions, their possible E/Z isomers, mixtures of E/Z and/or tautomers, in free form or in the form of salts.

Examples to obtain

Example 1: Obtain 1-(2-chloropyrid-5-ylmethyl)-2-nitro-3-methylguanine

A mixture of 1.5 g of 1-(2-chloropyrid-5-ylmethyl)-2-nitramino-3-methyl-5-n-propyl-1,3,5-triazacyclohexane, 0.5 g of solid sodium bicarbonate, 20 ml of methanol and 10 ml of water is stirred for 24 h at 50oC. Then the reaction mixture is evaporated and the residue purified on silica gel, using as is the temperature of the melting point 149-151o(Compound 2.2).

Example 2: Obtain 1-(2-chlorothiazole-5-ylmethyl)-2-nitro-3-methylguanine

A mixture of 1.5 g of 1-(2-chlorothiazole-5-ylmethyl)-2-nitramino-3,5-dimethyl-1,3,5-triazacyclohexane, 0.3 g Panso320 ml methanol and 20 ml of water is stirred for 16 h at 50oC. Then the reaction mixture was poured onto 100 ml of ethyl ether, acetic acid and the aqueous phase is separated. The organic phase is evaporated and the residue purified on silica gel, using as eluents dichloromethane/methanol in the ratio 95:5. This way, get listed in the title compound with a melting point 167-169o(Connection 2.45).

Example 3: Obtain 1-(2-chloropyridin-5-ylmethyl)-2-nitroguanidine

A mixture of 1.5 g of 1-(2-chloropyridin-5-ylmethyl)-2-nitramino-5-n-propyl-1,3,5-triazacyclohexane, 0,77 g NaHCO320 ml of methanol and 10 ml of water is stirred for 21 h at 50oC. Then the reaction mixture was poured onto 100 ml of ethyl ester of acetic acid, the aqueous phase is separated and the organic phase is washed with water. In conclusion, the organic phase is evaporated and the residue purified on silica gel, using as eluents dichloromethane/methanol in the ratio of 10:1.

In this way receive specified in the header connection the arts 1-3, can be obtained the following compounds of formula I are presented in table. 2. The abbreviated name "C-cut" refers to cyclopropyl.

1. The method of obtaining the compounds of formula I

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in which R1denotes hydrogen or C1-C4alkyl;

R2denotes hydrogen, C1-C6alkyl, C3-C6cycloalkyl or residue-CH2IN;

And denotes unsubstituted or, depending on the possibilities of substitution of the cyclic system from one - to five-fold substituted by substituents selected from the group comprising halogen, C1-C3alkyl, C1-C3alkoxy, halogen-C1-C3alkyl, C1-C3halogenoalkane, cyclopropyl, halogenlampen,2-C3alkenyl,2-C3quinil,2-C3halogenoalkanes and C2-C3halogenoalkanes,

WITH1-C3alkylthio,1-C3allogenicity, allyloxy, propargyloxy, allylthio, propargite, halogenations, halogenierte, cyan and nitro, aromatic or non-aromatic, monocyclic or bicyclic heterocyclic residue;

In denotes phenyl, 3-pyridyl or thiazolyl, under certain conditions, hung in the surrounding1-C3alkyl, C1-C3halogenated, cyclopropyl, halogenlampen,2-C3alkenyl,2-C3quinil,1-C3alkoxy, C2-C3halogenoalkanes,2-C3halogenoalkanes,1-C3halogenoalkane,1-C3alkylthio, C1-C3allogenicity, allyloxy, propargyloxy, allylthio, propargite, halogenations, halogenierte, halogen, cyano and nitro;

and under certain conditions it is possible E/Z-isomers, mixtures of E/Z-isomers and/or tautomers, in free form or in the form of salts carried out by hydrolysis of the compounds of formula II

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in which R1, R2and a have the same meaning as indicated for formula I;

R3denotes unsubstituted or substituted C1-C10alkyl, C3-C6cycloalkyl, phenyl or benzyl,

characterized in that the reaction is carried out at pH = 8 to 12.

2. The method according to p. 1 obtain the compounds of formula I in free form.

3. The method according to p. 1 obtain the compounds of formula I, in which1denotes hydrogen.

4. The method according to p. 1 obtain the compounds of formula I, in which 2denotes hydrogen, With whom I formula II, in which R3represents C1-C3alkyl, cyclopropyl, cyclohexyl, phenyl or benzyl.

6. The method according to p. 1 obtain the compounds of formula I, where And denotes the 2-chloropyrid-5-yl, tetrahydrofuran-3-yl, 5-methyltetrahydrofuran-3-yl or 2-chlorothiazole-5-yl.

7. The method according to any of paragraphs.1-6 obtain the compounds of formula 1, characterized in that it is carried out in water, alcohol or a mixture of water and alcohol.

 

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