Method of producing pesticide compounds

FIELD: chemistry.

SUBSTANCE: present invention relates to a method of producing a compound (I), where X is N or CR4; R1 is CN or CSNH2; R2 and R4 are independently hydrogen or chlorine; and R3 is halogen, haloalkyl, haloalkoxy or SF5, n equals 0, 1 or 2. The method involves, at the first step, reaction of a compound of formula (IV), where X, R1, R2, R3, R4 and n assume values given above, with formaldehyde or a formaldehyde trimer or chemical equivalent thereof, to obtain an intermediate compound (V), where X, R1, R2, R3, R4 and n assume values given above; and at the second step, reaction of the compound of formula (V) with a reducing agent, preferably sodium borohydride. The invention also relates to an intermediate compound 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-hydroxymethylamino-4-trifluoromethyl thionyl pyrazole.

EFFECT: efficient method of obtaining the compounds.

3 cl, 1 ex

 

The present invention relates to a method for producing substituted pyrazole compounds.

The pyrazoles, such as compounds 5-amino-1-aryl-3-cyanopyridine, and their derivatives, such as fipronil, constitute an important class of insecticides. As described in the application WO 00/35884 and U.S. patent 5556873, some substituted compound 5-N-alkyl-N-alkoxyamino-1-aryl-3-cyanopyridine have valuable pesticidal properties.

The applicant developed a new method of synthesis for the preparation of intermediate compounds suitable for obtaining pesticide compounds substituted pyrazole.

Thus, the present invention relates to a method of obtaining compounds of General formula (I)

where

X is N or CR4;

R1represents CN or CSNH2;

R2represents a hydrogen or chlorine; and

R3represents halogen, or halogenated, or halogenoalkane, or SF5,

interaction of the compound (IV)

with formaldehyde or trimer of formaldehyde or its chemical equivalent, to obtain the intermediate compound (V)

where R1, R2, R3have the values specified above.

Then the intermediate compound (V) can interact with the regenerating agent to receive the deposits of the compound (I). Suitable reducing agent comprises sodium borohydride. Reducing agent may be present in an amount of from 1 to 5 equivalents.

Some of the compounds of the formula (V) are novel compounds, and in particular, another aspect of the present invention is a new connection:

3-cyano-1-(2,6-dichloro-4-triptoreline)-5-hydroxymethylamino-4-triftormetilfullerenov (compound V).

The compound (I)obtained by the method of the present invention, can be used as a starting material for the synthesis of another important pyrazole, which is known to possess pesticidal properties and which corresponds to the General formula (VI).

where

R1represents CN or CSNH2;

X represents N or CR4;

each R2and R4independently represent hydrogen or chlorine;

R3represents halogen, halogenated, halogenoalkane or SF5;

each R5and R6independently represents alkyl group; and

n is 0, 1 or 2.

Obtaining this compound from the compound (I) is known from international patent application WO 00/35884, which is incorporated here by reference. In particular, compound (I) reacts with ethoxyacetylene in the presence of triethylamine to obtain compound (VI).

Next infusion is her invention will be illustrated in the following examples, not limiting the invention.

Example 1

5 equivalents of sodium methylate (30% solution in methanol) just added to the suspension 0,437 g of fipronil and 1.4 equivalents of paraformaldehyde in 3 ml of methanol to obtain 3-cyano-l-(2,6-dichloro-4-triptoreline)-5-hydroxymethylamino-4-triftormetilfullerenov (compound V) after 3 hours at 20°C and 1 hour at 60°C. Then to the intermediate product was added 1 equivalent of sodium borohydride to obtain the classical extraction and chromatographic separation of 3-cyano-1-(2,6-dichloro-4-triptoreline)-5-methylamino-4-triftormetilfullerenov (compound I).

1. The method of obtaining the compound (I),

where X is N or CR4;
R1represents CN or CSNH2;
R2and R4independently represent hydrogen or chlorine; and
R3represents halogen, halogenated, halogenoalkane or SF5, n is 0, 1 or 2;
including in the first stage, the interaction of the compounds of formula (IV)

where X is N or CR4;
R1represents CN or CSNH2;
R2and R4independently represent hydrogen or chlorine; and
R3represents halogen, halogenated, halogenoalkane or SF5, n is 0, 1 or 2,
with formaldehyde or trimer of formaldehyde, or the chemical equivalent of obtaining the intermediate (V)

where X, R1, R2, R3, R4and n have the meanings defined above; and
in the second stage, the interaction of the compound (V) with a regenerating agent.

2. The method according to claim 1, wherein the reducing agent is sodium borohydride.

3. The compound 3-cyano-1-(2,6-dichloro-4-triptoreline)-5-hydroxymethylamino-4-triftormetilfullerenov.



 

Same patents:

FIELD: chemistry.

SUBSTANCE: invention proposes 5-member heterocyclic inhibitors of kinase p38, including kinase p38α and kinase p38β, based on pyrazoles and imidazoles, with the general formula given below , in which ring B is phenyl, and C is a pyrazole or imidazole ring, and the rest of the symbols assume values given in paragraph 1 of the formula of invention.

EFFECT: there are described pharmaceutical compositions containing said compounds, as well as methods of using the compounds and compositions, including a method of treating, preventing or suppressing one or more symptoms of diseases and conditions mediated by kinase p38 which include, but not limited to, inflammatory diseases and conditions.

31 cl, 6 tbl, 175 ex

FIELD: medicine.

SUBSTANCE: invention is related to antagonists of serotonin 5-HT6 receptors of common formula 1 and their pharmaceutically acceptable salts and/or hydrates, pharmaceutical compositions, dosage forms and methods of production. Invention also includes new compounds of formula 1.1. In formulae 1 and 1.1 , Ar represents aryl, selected from unnecessarily substituted phenyl or unnecessarily substituted 5-6-member heteroaryl, which contains atom of nitrogen or atom of sulfur and heteroatom; R1 represents atom of hydrogen, unnecessarily substituted C1-C5 alkyl; Ar represents aryl, selected from unnecessarily substituted phenyl or unnecessarily substituted 5-6-member heteroaryl, which contains atom of nitrogen or atom of sulfur as heteroatom; R1 represents atom of hydrogen, which is unnecessarily substituted C1-C5 alkyl; R21,R22, R31, R32 independently from each other represent atom of hydrogen or substituent of aminogroup, selected from unnecessarily substituted C1-C4 alkyl, unnecessarily substituted phenyl, or R31 and R32 together with atom of nitrogen, to which they are bound, create unnecessarily substituted saturated 6-member heterocycle, possibly containing atom of nitrogen in cycle; or R1 together with atom of nitrogen, to which it is bound, and R21 and R22 together with atom of nitrogen, to which they are bound, create substituted pyrimidine cycle. In formula 1.1 R4, R5 and R6 independently from each other represent atom of hydrogen, unnecessarily substituted C1-C3 alkyl or phenyl.

EFFECT: compounds of invention may find application for treatment and prevention of development of conditions and disorders of central nervous system.

13 cl, 11 dwg, 4 tbl, 11 ex

FIELD: chemistry.

SUBSTANCE: described are derivatives of 5-substituted alkylaminopyrazoles of formula (I) , where R1 stands for CN, W stands for C-halogen; R2 stands for halogen, R3 stands for (C1-C3)-halogenoalkyl, R4 stands for (C1-C6)-alkyl, A stands for (C1-C12)-alkylene, R5 stands for (C1-C6)-alkyl, R6 stands for (C1-C6)-halogenoalkyl, n equals 2, or their pesticidely acceptable salts. Compounds demonstrate insecticidal activity and parasiticidal activity. The method of obtaining formula (I) is described, including interaction of compound of formula (II) with compound of formula (III) R5-O-A-NH2 and interaction on compound obtained with compound of formula (V) R4-L1.

EFFECT: obtaining derivatives which can be applied as pesticides.

3 cl, 6 tbl, 18 ex

FIELD: organic chemistry.

SUBSTANCE: invention describes insecticide-acaricide substance used against extoparasites in dogs and cats. Substance represents derivative of phenylpyrazole of the formula (I) wherein in pyrazole structure cyano-group, trifluoromethylsulfenyl group and amino-group are bound at 3, 4 and 5 positions, respectively, and chlorine atoms are bound to phenyl cycle at 2 and 6 positions, and trichlorosilyl group is bound at 4 position. Substance protects dogs and cats against infection with fleas for 65 days after treatment and for 45 days after treatment of cats, and against infection with mites for 35 days, not less. In acute experiment toxicity of substance is characterized by value LD50 above 1300 mg/kg after its administration in stomach to dogs.

EFFECT: valuable properties of substance.

2 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to 5-substituted alkylaminopyrazole derivatives of formula I , wherein R1 is CN; W is C-halogen; R1 is halogen; R3 is C1-C3-haloalkyl, C1-C3-haloalkoxy; R4 is hydrogen, C1-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, COR8; A is C1-C12-alkylene; R5 is hydrogen, C3-C6-alkenyl, -(CH )qR7 or NR10R11; R5 is C1-C6-haloalkyl; as well as method for animal exogenous and endogenous pest controlling; pesticide composition and application of said compounds for production of veterinary drug. 5-Substituted alkylaminopyrazole derivatives are useful in pest controlling, including insects, arachnids and helminthes, such as nematodes.

EFFECT: new pesticide derivatives.

9 cl, 12 tbl, 20 ex

FIELD: organic chemistry, pesticides.

SUBSTANCE: invention relates to production of compounds of formula I

, wherein R1 represents CN or CSNH2; X represents N or CR4; R2 and R4 represent hydrogen or chlorine; and R3 represents halogen, haloalkyl, halooxy or SF5. Claimed method includes reaction of compound of formula II

with aqueous acid solution. Also disclosed are method for production of intermediate of formula II, method for production of compound of formula I including step of production of formula II followed by conversion thereof to target compound. Moreover disclosed are two intermediates for production of target products.

EFFECT: new pesticide compounds and method for production thereof.

13 cl, 2 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to method for production of compounds of general formula I wherein R1 represents CN or CSNH2; X represents N or C each R2 and R4 are independently hydrogen or chlorine; R3 represents halogen, haloalkyl, haloalkoxy or SF3; R5 and R6 are independently alkyl; n = 0, 1 or 2. Claimed method includes reaction of compound of formula II , wherein substituents are as defined above; W represent hydrogen, with metal inorganic salt or organic amine to form salt of compound II as intermediate and further reaction of said salt with alkylating agent of formula III wherein R6 is as defined above; Y represents leaving group. In another embodiment compounds of formula I are obtained by reaction of metal inorganic salt or organic base of formula II with abovementioned alkylating agent of formula III.

EFFECT: essentially decreased formation of side products; target products of high purity.

37 cl, 4 ex

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention elates to novel derivatives of uracil of the formula [I] possessing herbicide activity, a herbicide composition based on thereof and to a method for control of weeds. In derivatives of uracil of the formula [I] the group Q-R3 represents a substituted group taken among:

wherein a heterocyclic ring can be substituted with at least a substitute of a single species taken among the group involving halogen atom, (C1-C6)-alkyl-(C1-C6)-alkoxy; Y represents oxygen, sulfur atom, imino-group or (C1-C3)-alkylimino-group; R1 represents (C1-C3)-halogenalkyl; R2 represents (C1-C3)-alkyl; R3 represents OR7, SR8 or N(R9)R10; X1 represents halogen atom, cyano-group, thiocarbamoyl or nitro-group; X2 represents hydrogen or halogen atom wherein each among R7, R8 and R10 represents independently carboxy-(C1-C6)-alkyl and other substitutes given in the invention claim; R9 represents hydrogen atom or (C1-C6)-alkyl. Also, invention relates to intermediate compounds used in preparing uracil derivatives.

EFFECT: improved preparing method, valuable properties of compounds.

40 cl, 16 sch, 12 tbl, 65 ex

The invention relates to 1-methyl-5-alkylsulfonyl-, 1-methyl-5-alkylsulfonyl - 1-methyl-5-alkylthiomethyl pyrazolylborate and herbicide tool based on them

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention elates to novel derivatives of uracil of the formula [I] possessing herbicide activity, a herbicide composition based on thereof and to a method for control of weeds. In derivatives of uracil of the formula [I] the group Q-R3 represents a substituted group taken among:

wherein a heterocyclic ring can be substituted with at least a substitute of a single species taken among the group involving halogen atom, (C1-C6)-alkyl-(C1-C6)-alkoxy; Y represents oxygen, sulfur atom, imino-group or (C1-C3)-alkylimino-group; R1 represents (C1-C3)-halogenalkyl; R2 represents (C1-C3)-alkyl; R3 represents OR7, SR8 or N(R9)R10; X1 represents halogen atom, cyano-group, thiocarbamoyl or nitro-group; X2 represents hydrogen or halogen atom wherein each among R7, R8 and R10 represents independently carboxy-(C1-C6)-alkyl and other substitutes given in the invention claim; R9 represents hydrogen atom or (C1-C6)-alkyl. Also, invention relates to intermediate compounds used in preparing uracil derivatives.

EFFECT: improved preparing method, valuable properties of compounds.

40 cl, 16 sch, 12 tbl, 65 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to method for production of compounds of general formula I wherein R1 represents CN or CSNH2; X represents N or C each R2 and R4 are independently hydrogen or chlorine; R3 represents halogen, haloalkyl, haloalkoxy or SF3; R5 and R6 are independently alkyl; n = 0, 1 or 2. Claimed method includes reaction of compound of formula II , wherein substituents are as defined above; W represent hydrogen, with metal inorganic salt or organic amine to form salt of compound II as intermediate and further reaction of said salt with alkylating agent of formula III wherein R6 is as defined above; Y represents leaving group. In another embodiment compounds of formula I are obtained by reaction of metal inorganic salt or organic base of formula II with abovementioned alkylating agent of formula III.

EFFECT: essentially decreased formation of side products; target products of high purity.

37 cl, 4 ex

FIELD: organic chemistry, pesticides.

SUBSTANCE: invention relates to production of compounds of formula I

, wherein R1 represents CN or CSNH2; X represents N or CR4; R2 and R4 represent hydrogen or chlorine; and R3 represents halogen, haloalkyl, halooxy or SF5. Claimed method includes reaction of compound of formula II

with aqueous acid solution. Also disclosed are method for production of intermediate of formula II, method for production of compound of formula I including step of production of formula II followed by conversion thereof to target compound. Moreover disclosed are two intermediates for production of target products.

EFFECT: new pesticide compounds and method for production thereof.

13 cl, 2 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to 5-substituted alkylaminopyrazole derivatives of formula I , wherein R1 is CN; W is C-halogen; R1 is halogen; R3 is C1-C3-haloalkyl, C1-C3-haloalkoxy; R4 is hydrogen, C1-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, COR8; A is C1-C12-alkylene; R5 is hydrogen, C3-C6-alkenyl, -(CH )qR7 or NR10R11; R5 is C1-C6-haloalkyl; as well as method for animal exogenous and endogenous pest controlling; pesticide composition and application of said compounds for production of veterinary drug. 5-Substituted alkylaminopyrazole derivatives are useful in pest controlling, including insects, arachnids and helminthes, such as nematodes.

EFFECT: new pesticide derivatives.

9 cl, 12 tbl, 20 ex

FIELD: organic chemistry.

SUBSTANCE: invention describes insecticide-acaricide substance used against extoparasites in dogs and cats. Substance represents derivative of phenylpyrazole of the formula (I) wherein in pyrazole structure cyano-group, trifluoromethylsulfenyl group and amino-group are bound at 3, 4 and 5 positions, respectively, and chlorine atoms are bound to phenyl cycle at 2 and 6 positions, and trichlorosilyl group is bound at 4 position. Substance protects dogs and cats against infection with fleas for 65 days after treatment and for 45 days after treatment of cats, and against infection with mites for 35 days, not less. In acute experiment toxicity of substance is characterized by value LD50 above 1300 mg/kg after its administration in stomach to dogs.

EFFECT: valuable properties of substance.

2 ex

FIELD: chemistry.

SUBSTANCE: described are derivatives of 5-substituted alkylaminopyrazoles of formula (I) , where R1 stands for CN, W stands for C-halogen; R2 stands for halogen, R3 stands for (C1-C3)-halogenoalkyl, R4 stands for (C1-C6)-alkyl, A stands for (C1-C12)-alkylene, R5 stands for (C1-C6)-alkyl, R6 stands for (C1-C6)-halogenoalkyl, n equals 2, or their pesticidely acceptable salts. Compounds demonstrate insecticidal activity and parasiticidal activity. The method of obtaining formula (I) is described, including interaction of compound of formula (II) with compound of formula (III) R5-O-A-NH2 and interaction on compound obtained with compound of formula (V) R4-L1.

EFFECT: obtaining derivatives which can be applied as pesticides.

3 cl, 6 tbl, 18 ex

FIELD: medicine.

SUBSTANCE: invention is related to antagonists of serotonin 5-HT6 receptors of common formula 1 and their pharmaceutically acceptable salts and/or hydrates, pharmaceutical compositions, dosage forms and methods of production. Invention also includes new compounds of formula 1.1. In formulae 1 and 1.1 , Ar represents aryl, selected from unnecessarily substituted phenyl or unnecessarily substituted 5-6-member heteroaryl, which contains atom of nitrogen or atom of sulfur and heteroatom; R1 represents atom of hydrogen, unnecessarily substituted C1-C5 alkyl; Ar represents aryl, selected from unnecessarily substituted phenyl or unnecessarily substituted 5-6-member heteroaryl, which contains atom of nitrogen or atom of sulfur as heteroatom; R1 represents atom of hydrogen, which is unnecessarily substituted C1-C5 alkyl; R21,R22, R31, R32 independently from each other represent atom of hydrogen or substituent of aminogroup, selected from unnecessarily substituted C1-C4 alkyl, unnecessarily substituted phenyl, or R31 and R32 together with atom of nitrogen, to which they are bound, create unnecessarily substituted saturated 6-member heterocycle, possibly containing atom of nitrogen in cycle; or R1 together with atom of nitrogen, to which it is bound, and R21 and R22 together with atom of nitrogen, to which they are bound, create substituted pyrimidine cycle. In formula 1.1 R4, R5 and R6 independently from each other represent atom of hydrogen, unnecessarily substituted C1-C3 alkyl or phenyl.

EFFECT: compounds of invention may find application for treatment and prevention of development of conditions and disorders of central nervous system.

13 cl, 11 dwg, 4 tbl, 11 ex

FIELD: chemistry.

SUBSTANCE: invention proposes 5-member heterocyclic inhibitors of kinase p38, including kinase p38α and kinase p38β, based on pyrazoles and imidazoles, with the general formula given below , in which ring B is phenyl, and C is a pyrazole or imidazole ring, and the rest of the symbols assume values given in paragraph 1 of the formula of invention.

EFFECT: there are described pharmaceutical compositions containing said compounds, as well as methods of using the compounds and compositions, including a method of treating, preventing or suppressing one or more symptoms of diseases and conditions mediated by kinase p38 which include, but not limited to, inflammatory diseases and conditions.

31 cl, 6 tbl, 175 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to a method of producing a compound (I), where X is N or CR4; R1 is CN or CSNH2; R2 and R4 are independently hydrogen or chlorine; and R3 is halogen, haloalkyl, haloalkoxy or SF5, n equals 0, 1 or 2. The method involves, at the first step, reaction of a compound of formula (IV), where X, R1, R2, R3, R4 and n assume values given above, with formaldehyde or a formaldehyde trimer or chemical equivalent thereof, to obtain an intermediate compound (V), where X, R1, R2, R3, R4 and n assume values given above; and at the second step, reaction of the compound of formula (V) with a reducing agent, preferably sodium borohydride. The invention also relates to an intermediate compound 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-hydroxymethylamino-4-trifluoromethyl thionyl pyrazole.

EFFECT: efficient method of obtaining the compounds.

3 cl, 1 ex

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