RU2083562C1 - Pyridine derivatives, process for preparation thereof, insecticidal composition - Google Patents

Abstract

FIELD: agriculture, more particularly plant protection. SUBSTANCE: product of formula:

wherein X is oxygen or sulfur atom; R¹ is H, lower alkyl which may be substituted, lower alkenyl, lower alkynyl, C₃-C₆ cycloalkyl, C(W¹)R³, W¹ is oxygen or sulfur atom; R³ is lower alkyl, lower alkoxy (lower alkyl) thio, (lower alkyl) amino; SO₂R⁴; R⁴ is lower alkyl, di(lower alkyl) amino, NHR⁵; R⁵ is 2-pyridyl; R² is hydrogen, lower alkyl which is substituted by lower alkyl lower alkoxy, (lower alkyl) thio, trifluoromethylpyridyl, SO₂R⁴; R⁴ is lower alkyl; R¹ and R² taken together form C(R⁶)(R⁷); R⁶ and R⁷ are lower alkoxy, (lower alkyl) thio; R¹ and R² together with nitrogen atom form morphaline ring, 2-cyanoimino-3- methyl-1,3-diazolidine ring, m is 0 or 1. Reagent 1: n- trifluoromethylpyridine-3-carboxylic acid or reactive derivative thereof. Reagent 2: HN(R¹)R² insecticidal composition based on said product. EFFECT: improved properties of the insecticidal composition. 10 cl, 1 tbl

Description

 The invention relates to amide compounds and their salts, methods for their preparation and pesticidal compositions containing them as active ingredients.

 Various compounds are known as active ingredients for pesticides. However, their chemical structures are different from the amide compounds of the present invention.

 To date, organophosphorus compounds, carbamate compounds and pyrethroid compounds have been used as active ingredients for pesticides, such as insecticides. As a result, some harmful insects in recent years have become resistant to such insecticides. Therefore, there is a need for a pesticide effective against pests having such resistance. Further, they conducted research and development of a new pesticide, which is more effective against harmful insects and safer for fish, aquatic armored animals and domestic animals or which has a wider pesticidal spectrum.

 The aim of the present invention is to provide amide compounds having pesticidal activity, methods for their preparation and pesticidal compositions containing them.

 The inventors of the present invention conducted extensive research to develop pesticides and found that amide compounds having a specific chemical structure have excellent pesticidal properties. The present invention is made based on this finding.

где X представляет собой атома кислорода или атом серы;
Y представляет собой галоидалкильную группу;
каждый R¹ и R², независимо друг от друга, представляет собой атом водорода, алкильную группу, которая может быть замещена, алкенильную группу, которая может быть замещена, алкинильную группу, которая может быть замещена, -C(W')R³, S(O)_nR⁴ или -NHR⁵, либо R¹ и R² вместе образуютC(R⁶)R⁷ или вместе с соседним атомом азота образуют C_4-5 5- или 6-членную гетероциклическую группу, которая может содержать атом азота или атом кислорода;
R³ представляет собой алкильную группу, которая может быть замещена, алкенильную группу, которая может быть замещена, алкинильную группу, которая может быть замещена, циклоалкильную группу, которая может быть замещена, арильную группу, которая может быть замещена, алкоксильную группу, алкилтиогруппу или моно- или диалкиламиногруппу;
R⁴ представляет собой алкильную группу или диалкиламиногруппу;
R⁵ представляет собой алкильную группу или арильную группу;
каждый из R⁶ и R⁷ независимо друг от друга представляет собой алкоксильную группу или алкилтиогруппу;
W' представляет собой атом кислорода или атом серы;
m есть 0 или 1;
n 1 или 2;
способ получения указанного амидного соединения и содержащую его пестицидную композицию.Thus, the present invention provides an amide compound of formula (1) or a salt thereof:

where X represents an oxygen atom or a sulfur atom;
Y represents a haloalkyl group;
each R ¹ and R ² , independently of one another, represents a hydrogen atom, an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, —C (W ′) R ³ , S (O) _n R ⁴ or —NHR ⁵ or R ¹ and R ² together form a C (R ⁶ ) R ⁷ or together with an adjacent nitrogen atom form a C _4-5 5- or 6-membered heterocyclic group which may contain an atom nitrogen or an oxygen atom;
R ³ represents an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, a cycloalkyl group which may be substituted, an aryl group which may be substituted, an alkoxyl group, an alkylthio group or a mono - or a dialkylamino group;
R ⁴ represents an alkyl group or a dialkylamino group;
R ⁵ represents an alkyl group or an aryl group;
each of R ⁶ and R ⁷ independently of one another represents an alkoxyl group or an alkylthio group;
W 'represents an oxygen atom or a sulfur atom;
m is 0 or 1;
n is 1 or 2;
a method for producing said amide compound and a pesticidal composition containing it.

 Below the present invention is described in detail with reference to preferred options.

In formula (I), Y represents a haloalkyl group such as CF ₃ , CHF ₂ , CH ₂ F, CF ₂ CI, CFCI ₂ , CCI ₃ , CH ₂ CF ₃ , CF ₂ CF ₃ , CHBr ₂ , CH ₂ Br and things like that. Preferably, Y represents a haloalkyl group having from 1 to 2 carbon atoms and from 1 to 5 halogen atoms, more preferably trifluoromethyl.

A substituent of an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted or a cycloalkyl group which may be substituted, in the definition of each R ¹ , R ² and R ³ in the formula (1), may be, for example, a halogen atom; alkoxy; adkiltio; trialkylsilyl; phenyl; phenyl substituted with halogen, alkyl, alkoxy, nitro or haloalkyl; phenyl substituted with a phenoxy group which may be substituted with alkoxy or alkcolthio; phenoxy; phenylthio; amino; an amino group substituted with one or two alkyls; A C _2-6 cyclic amino group; morpholino; substituted alkyl morpholino group; 1-piperidinyl; 1-piperidinyl substituted with alkyl, phenyl, pyridyl or trifluoromethylpyridyl; hydroxy; cyano; cycloalkyl; amino; - C (W ² ) R ⁸ , where N ² represents an oxygen atom or a sulfur atom, R ⁸ represents a hydrogen atom, an amino, amino group substituted by one or two alkyls, alkyl, alkoxy, alkylthio or aryl or OC (W ² ) R ⁹ (where R ⁹ represents alkyl or aryl substituted with haloalkyl); or alkylsulfonyl. When the above substituent is an imino group, it can form an amidino group or an imidate group together with an amino group or an alkoxy group.

где Y и R² имеют вышеуказанные значения, а А представляет собой

, l есть целое число от 1 до 4 и q есть 1 или 2. Конкретно, соединение согласно формуле представляет собой димер, в котором соединения формулы (1) соединены, например, алкиленовой цепью. Аналогично, соединение согласно настоящему изобретению включает тример, основанный на той же концепции.A substituent for an alkyl group which may be substituted in the definition of each R ¹ and R ² includes, for example, a 4-haloalkyl-3-pyridinecarboxamide group, an N-methyl-4-haloalkyl-3-pyridinecarboxamide group, and 4-haloalkyl-3 -pyridinecarboxamide-N-alkyleneoxy group. The chemical structure of formula (1) containing such a substituent can be represented, for example, by the following formula:

where Y and R ² have the above meanings, and A represents

, l is an integer from 1 to 4 and q is 1 or 2. Specifically, the compound according to the formula is a dimer in which the compounds of formula (1) are connected, for example, by an alkylene chain. Similarly, the compound of the present invention includes a trimer based on the same concept.

The substituent of the aryl group which may be substituted in the definition of R ³ in the formula (1) can be, for example, a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, cycloalkyl, cycloalkoxy, alkoxycarbonyl, alkylcarbonyl, alkylcarbonyloxy, aryl, aryloxy an arylthio, amino, amino group substituted with one or two alkyls, cyano, nitro or hydroxy.

In the formula (1), the alkyl group or the alkyl part included in R ¹ or R ² can be, for example, an alkyl group or an alkyl part having from 1 to 6 carbon atoms, such as a methyl group, an ethyl group, a propyl group, butyl a group, a pentyl group or a hexyl group, and in the case of 3 or more carbon atoms, have a linear or branched isomeric structure. An alkenyl group included in R ¹ and R ² may, for example, be a group having from 2 to 6 carbon atoms, such as an ethenyl group, propenyl group, butenyl group, pentenyl group or hexenyl group and in the case of three or more carbon atoms may have a linear or branched isomeric structure. An alkyl group included in R ¹ and R ² may, for example, be a group having from 2 to 6 carbon atoms, such as an ethynyl group, a propyl group, a butynyl group, a pentinyl group or a hexynyl group and in the case of three or more carbon atoms may have a linear or branched isomeric structure. A cycloalkyl group included in R ¹ or R ² may, for example, be a group having from 3 to 8 carbon atoms, a cyclopentyl group or a cyclohexyl group.

In the formula (1), a C _4-5 5- or 6-membered heterocyclic group, which may contain a nitrogen atom or an oxygen atom formed by R ¹ and R ² together with an adjacent nitrogen atom, can, for example, be a morpholino group, pyrrolidino group, piperidino group, 1-imidazolidyl group, 2-cyanoimino-3-methyl-1-imidazolidyl group, 1-piperadinyl group or 4-methyl-2-piperadinyl group.

 The aryl group mentioned in the definition of formula (1) may be, for example, a phenyl group, a thienyl group, a furanyl group, a pyridyl group, a naphthyl group, a benzothienyl group, a benzofuranyl group, or a quinolinyl group.

 The compound of formula (1) can form a salt with an acidic substance or a basic substance. The salt with the acidic substance may be an inorganic salt, such as hydrochloride, hydrobromide, phosphate, sulfate or nitrate. The salt with the basic material may be a salt of an inorganic or organic base, such as sodium salt, potassium salt, calcium salt, ammonium salt or dimethylamine salt.

The amide compound or its salt according to the present invention is preferably the following compound:
(1) A compound of formula (1) or a salt thereof, in which X is an oxygen atom.

(2) A compound of formula (1) or a salt thereof, in which each R ¹ and R ² that are independent of each other, represent a hydrogen atom, an alkyl group that may be substituted with —C (W ¹ ) R ³ , or R ¹ and R ² together form C (R ⁶ ) R ⁷ , is an oxygen atom or a sulfur atom, R ³ represents an alkyl group which may be substituted, an aryl group which may be substituted, or an alkoxyl group, and each R ⁶ and R ⁷ , which are independent of each other, represent an alkoxyl group or an alkylthio group.

More preferably, a compound of formula (1) or a salt thereof in which X represents an oxygen atom, each of R ¹ and R ² which are independent of each other, represents a hydrogen atom, an alkyl group, an alkoxyalkyl group, an alkylaminoalkyl group, C _{2- 6} cyclic aminoalkyl group gidroasialkilnuyu group, a cyanoalkyl group, tiokarbamoilalkilnuyu group alkilkarboniloksialkilnuyu group, an alkylcarbonyl group, an arylcarbonyl group, a trifluoromethyl-substituted arylcarbonyl group, an alkoxythiocarbonyl group or an alkoxycarbonyl group, or R ¹ and R ² together obrazuyutC (R ⁶⁾ R ⁷ and R ⁶ and R ⁷ represent an alkoxy group, an alkylthio group, respectively.

Specific examples of preferred compounds include the following compounds:
4-trifluoromethyl-3-pyridinecarboxamide, N-cyanomethyl-4-trifluoromethyl-3-pyridinecarboxamide, N-thiocarbamoylmethyl-4-trifluoromethyl-3-pyridinecarboxamide, N-ethoxymethyl-4-trifluoromethyl-3-apridine trifluoromethyl-3-pyridinecarboxamide, N-cyanomethyl-N, N-bis (4-trifluoromethylnicotinoyl) amine, N-acetyl-N-cyanomethyl-4-trifluoromethyl-3-pyridinecarboxamide, N-cyanomethyl-N-methyl-4-trifluoromethylpyridine 3-carboxamide, N- (4-trifluoromethylnicotinoyl) thiocarbamic acid O-methyl ester, N-methyl-4-trifluoromethylpyridine-3-carboxamide, N- (N ', N'-dimethylamide inomethyl) -4-trifluoromethylpyridin-3-carboxamide, N- (1-piperidinyl) -4-trifluoromethylpyridin-3-carboxamide, N- cyano-methyl ester N- (4-trifluoromethyl-nicotinoyl) aminomethylpivalic acid, O, S-dimethyl ether N- ( 4-trifluoromethylnicotinol) iminoformic acid, N-hydroxymethyl-4-trifluoromethyl-3-pyridinecarboxamide, N-acetyl-4-trifluoromethyl-3-pyridinecarboxamide or N- (4-trifluoromethylnicotinoyl) carbamic acid methyl ester or 1-oxide.

или его реакционноспособное производное

(1-1)
В вышеприведенных формулах Y, R¹ и R² имеют вышеуказанное значение.The compound of formula (1) or its salt can be obtained, for example, by the following method (A):

or its reactive derivative

(1-1)
In the above formulas, Y, R ¹ and R ² have the above meaning.

 The reactive 4-haloalkylpyridin-3-carboxylic acid derivative of the formula (II) can be, for example, an acid halide, an ester or an acid anhydride.

 The above reaction is usually carried out in the presence of a solvent, if necessary, in the presence of a base. The solvent may be, for example, an aromatic hydrocarbon such as benzene or toluene; an ether such as diethyl ether or tetrahydrofuran; a halogenated hydrocarbon such as methylene chloride or chloroform; or an aprotic polar solvent such as acetonitrile, dimethylformamide or pyridine. These solvents can be used individually or in combination as a mixture. The base may be, for example, a tertiary amine, such as trimethylamine, triethylamine or pyridine; alkali metal hydroxide such as sodium hydroxide or potassium hydroxide; an alkali metal carbonate such as sodium carbonate or potassium carbonate; or an alkali metal alkoxide such as sodium methoxide or sodium ethoxide. When the reagent is 4-haloalkylpyridin-3-carboxylic acid, a condensation agent such as dicyclohexylcarbodiimide, N, N'-carbonyldimidazole or 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide is usually used.

The temperature of the above reaction usually ranges from -50 to +100 ^° C. However, when the reactive derivative is an acid halide or acid anhydride, the temperature preferably leaves from 0 to 30 ^° C., and when the reactive derivative is an ester, the temperature is preferably from 50 to 100 ^o C. The reaction time is usually from 0.1 to 24 hours

 A compound of formula (1) in which m is 1, i.e. a compound of the following formula (1-2), can be prepared by reacting a compound of the above formula (1-1) with an oxidizing agent.

где Y, R¹ и R² имеют вышеуказанное значение.

where Y, R ¹ and R ² have the above meaning.

This reaction is usually carried out in the presence of a solvent. As the solvent, mention may be made, for example, of acetic acid. As the oxidizing agent, hydrogen peroxide is usually used. The reaction temperature usually ranges from 50 to 100 ^o C, and the reaction time is usually from 6 to 24 hours

 A compound of formula (1) in which X is a sulfur atom can be prepared by reacting a compound of the above formula (1-1) with a sulfonation agent such as phosphorus pentasulfide.

The reaction is usually carried out in the presence of a solvent. The solvent used is preferably toluene or xylene. The temperature of the above reaction usually lies between 80 and 150 ^o C, preferably between 110 and 130 ^o C. The reaction time is usually from 1 to 12 hours

В вышеприведенных формулах Y, R¹ и R² имеют вышеуказанное значение при условии, что здесь R² отличен от водорода, а HaI является атомом галогена.Further, the compound of formula (1) or its salt can be obtained, for example, by the following method (B):

In the above formulas, Y, R ¹ and R ² have the above meaning, provided that here R ² is other than hydrogen and HaI is a halogen atom.

 The reaction according to method (B) can be carried out in the same way as the reaction according to the above method (A).

В вышеприведенных формулах R' и R являются алкильными группами, R" представляет собой атом водорода или алкильную группу.Further, other methods for preparing compounds of formula (1) or their salts can be mentioned, for example, the following:

In the above formulas, R 'and R are alkyl groups, R "represents a hydrogen atom or an alkyl group.

The reaction of the above method (C-1) can be carried out in the presence of a solvent or base. The solvent may be, for example, an aromatic hydrocarbon such as benzene or toluene; an ether such as tetrahydrofuran; a halogenated hydrocarbon such as methylene chloride or chloroform; or an aprotic polar solvent such as acetonitrile, dimethylformamide or pyridine. These solvents can be used individually or in combination as a mixture. As the base, a base such as triethylamine or pyridine is preferably used. The temperature of the above reaction usually lies between 0 and 50 ^o C, preferably between 20 and 40 ^o C, and the reaction time is usually from 1 to 6 hours

The reaction of the first half of the above method (C-2) can be carried out in the presence of hydrochloric gas and a solvent. The solvent, for example, may be an ether, such as tetrahydrofuran or diethyl ether; a halogenated hydrocarbon such as methylene chloride or chloroform; or an aromatic hydrocarbon such as benzene or nitrobenzene. These solvents can be used individually or in combination as a mixture. The reaction temperature usually ranges from -10 to +30 ^o C, preferably from -5 to 10 ^o C, and the reaction time is usually from 4 to 168 hours

The second half of the reaction can be carried out in the presence of a solvent. The solvent may be, for example, an alcohol such as methanol or ethanol. The reaction temperature is usually in the range from 0 to 80 ^o C, preferably from 20 to 50 ^o C, and the reaction time is usually from 1 to 8 hours

The reaction of the above method (C-3) can be carried out in the presence of a solvent. The solvent may be, for example, water or an alcohol, such as methanol or ethanol. Such solvents may be used individually or in combination as a mixture. The reaction temperature usually ranges from 10 to 100 ^o C, preferably from 20 to 80 ^o C, and the reaction time is usually from 1 to 12 hours

 The reaction of the above method (C-4) can be carried out under the same conditions as in the method (C-3).

The reaction of the above method (C-5) can be carried out in the presence of hydrochloric gas and a solvent. The solvent may be, for example, an ether such as dimethoxyethane or dioxane. The reaction temperature usually ranges from -50 to +50 ^o C, preferably from -30 to +20 ^o C. The reaction time is usually from 1 to 8 hours

The reactions of the above method (C-6) are three-stage. The reaction of the first stage is carried out in the presence of a solvent. The solvent may be, for example, an aromatic hydrocarbon such as benzene or toluene; an ether such as diethyl ether or tetrahydrofuran; a halogenated hydrocarbon such as methylene chloride or chloroform; or an aprotic polar solvent, such as acetonitrile or dimethylformamide. Such solvents may be used individually or in combination as a mixture. The reaction temperature usually lies between 30 and 120 ^o C, preferably between 50 and 80 ^o C, and the reaction time is usually from 1 to 12 hours

The second stage reaction is carried out in the presence of a solvent. The solvent may, for example, be the same solvent as mentioned for the first-stage reaction. The reaction temperature usually lies between 0 and 100 ^o C, preferably between 20 and 50 ^o C, and the reaction time is usually from 1 to 12 hours

The third stage reaction is carried out in the presence of a solvent and a base. The solvent may be, for example, an aprotic polar solvent such as acetonitrile or dimethylformamide. The base may be, for example, an alkali metal hydride, such as sodium hydride or potassium hydride; alkali metal hydroxide such as sodium hydroxide or potassium hydroxide; alkali metal alkoxide such as sodium methoxide or sodium ethoxide; or a tertiary amine such as triethylamine or pyridine. The reaction temperature usually ranges from 0 to 100 ^o C, preferably from 20 to 50 ^o C, and the reaction time is usually from 1 to 12 hours

Стадию (D-1) осуществляют путем проведения реакции 2,6-дихлор-3-циано-4-4трифторметилпиридина с концентрированной серной кислотой.Among the compounds of formula (I), a compound in which X represents an oxygen atom, Y represents CF ₃ , and R ¹ and R ² are simultaneously hydrogen atoms, i.e. 4-trifluoromethyl-3-pyridinecarboxamide, can be prepared as described above. method (A) using ammonia as a compound of formula (III). In other words, it can be obtained as follows from 2,6-dichloro-3-cyano-4-trifluoromethylpyridine:

Stage (D-1) is carried out by reacting 2,6-dichloro-3-cyano-4-4 trifluoromethylpyridine with concentrated sulfuric acid.

 Stage (D-2) is carried out by reacting hydrogen with 2,6-dichloro-4-trifluoromethyl-3-pyridinecarboxamide obtained in the previous stage (D-1) in the presence of a solvent, catalyst and base. The solvent may be, for example, an alcohol, such as methanol or ethanol, or an ether, such as tetrahydrofuran. The catalyst may be, for example, palladium or palladium (II) chloride. The base may be, for example, sodium acetate, sodium hydroxide, potassium hydroxide or triethylamine.

The reaction temperature in stage (D-2) usually lies between 0 and 100 ^o C, and the reaction time is usually from 1 to 24 hours

 Further, in the above step (D-1), a similar reaction can be carried out using 2,6-dibromo-3-cyan-4-trifluoromethylpyridine instead of 2,6-dichloro-3-cyan-4-trifluoromethylpyridine. This 2,6-dibromo-3-cyano-4-trifluoromethylpyridine can be prepared by reacting 3-cyano-2,6-dihydroxy-4-trifluoromethylpyridine with a brominating agent such as phosphorus oxybromide.

Among the compounds of formula (II), a compound in which Y is CF ₃ , i.e. 4-trifluoromethylpyridin-3-carboxylic acid is a known compound and is commercially available.

 Further, 4-haloalkylpyridin-3-carboxylic acid can be obtained, for example, as follows.

Стадия 1 может осуществляться путем проведения реакции 2,6-дихлор-4-галоидалкилпиридина с газообразным или твердым диоксидом углерода в присутствии литийдиалкиламида (предпочтительно литийдиизопропиламида) и растворителя. Растворителем может быть эфир, такой как тетрагидрофуран или диэтиловый эфир. Температура реакции обычно лежит между -100 и +20^oC, предпочтительно от -80 до -20^oC, а время реакции составляет от 1 до 12 ч.

Stage 1 can be carried out by reacting 2,6-dichloro-4-haloalkylpyridine with gaseous or solid carbon dioxide in the presence of lithium dialkylamide (preferably lithium diisopropylamide) and a solvent. The solvent may be an ether, such as tetrahydrofuran or diethyl ether. The reaction temperature usually lies between -100 and +20 ^o C, preferably from -80 to -20 ^o C, and the reaction time is from 1 to 12 hours

Step 2 can be carried out by reacting the 2,6-dichloro-4-haloalkylpyridin-3-carboxylic acid formed in step 1 with a chlorinating agent in the presence of a solvent. The chlorinating agent may be thionyl chloride or phosphorus pentachloride, and the solvent may be an aromatic hydrocarbon such as benzene or toluene. The reaction temperature is usually in the range from 20 to 120 ^o C, preferably from 50 to 100 ^o C, and the reaction time is from 1 to 6 hours

Stage 3 can be carried out by reacting the 2,6-dichloro-4-haloalkylpyridin-3-carboxylic acid formed in stage 2 with an alcohol in the presence of a base. The alcohol may be methanol or ethanol, and the base may be a tertiary base such as triethylamine or pyridine. The reaction temperature is usually in the range from 0 to 80 ^o C, preferably from 20 to 50 ^o C, and the reaction time is from 1 to 12 hours

Step 4 is carried out by reacting the 2,6-dichloro-4-haloalkylpyridin-3-carboxylic acid ester formed in step 3 with hydrogen gas in the presence of a solvent, catalyst and base. The solvent may be an alcohol, such as methanol or ethanol, or an ether, such as tetrahydrofuran; the catalyst may be palladium or palladium (II) chloride and the base may be a tertiary base such as triethylamine or pyridine, or sodium acetate. The reaction temperature is usually in the range from 0 to 100 ^o C, preferably from 20 to 50 ^o C, and the reaction time is from 1 to 24 hours

Step 5 is carried out by reacting the 4-haloalkylpyridin-3-carboxylic acid ester formed in step 4 with a base in the presence of a solvent. The solvent may be water or an alcohol, such as methanol or ethanol, and can be used individually or in combination as a mixture. The base may be an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide. The reaction temperature usually ranges from 0 to 100 ^o C, preferably from 20 to 80 ^o C, and the reaction time is from 1 to 12 hours

 In addition, a reactive derivative can be obtained from a compound of formula (II).

 The synthesis of acid chloride can be carried out by reacting 4-haloalkylpyridin-3-carboxylic acid with a chlorinating agent such as thionyl chloride or phosphorus trichloride, if necessary, in the presence of a catalytic amount of dimethylformamide at reflux temperature.

 A reactive derivative of the formula (II), other than 4-haloalkyl-3-pyridinecarbonyl chloride, can be obtained by a method similar to the usual method of converting benzoic acid into a reactive derivative. For example, an acid bromide can be obtained by reacting 4-haloalkylpyridine-3-carboxylic acid with a brominating agent such as phosphorus tribromide, phosphorus oxybromide or acetyl bromide; acid anhydride can be prepared by reacting 4-haloalkyl-pyridin-3-carboxylic acid or its acid chloride with a drying agent; ester can be obtained by reaction of 4-haloalkylpyridin-3-carboxylic acid with alcohol.

 The compounds of the present invention exhibit excellent properties as active ingredients for pesticides, for example, insecticides, miticides, nematicides and soil pesticides. For example, they are effective against ticks that parasitize plants, such as the two-spotted spider mite (Tetranychus urticae), the carmine spider mite (Tetranychus cinnabarinus), or the red citrus mite (Panonychus citri), or the root mite (Rhizoglyusus echin; aphids such as peach aphids (Myzus persicae) or cotton aphids (Aphis gossypii); agricultural harmful insects such as cabbage moth (Plutella xylostella), cabbage worm (Mamestra brassicae), common scoop (Spodoptera litura), Colorado potato beetle (Leptinotarsa decemlineata), apple moth (Laspeyresia pomonis cottonis) tobacco scoop (Heliothis virescens), cotton weevil (Anthonomus grandis), unpaired silkworm (Lymantria dispar), pumpkin leaf beetle (Aulacophora femoralis), delphacids, leafhoppers, mealybugs, bedbugs, whiteflies, thrips, grasshoppers, anthomidae, Agrotis ipsilon), scoop (Agrotis segetum) or ants; hygienic insects such as tropical rat mites (Ornithonyssus bacoti), cockroaches, housefly (Musca domestica) or common mosquito (Culex pipiens pallens); grain insect pests during storage, such as cereal moth (Sitotroga cerealella), azuki bean broom (Callosobruchus chinensis), small flour crusher (Tribolium confusum) or flour worm; insects that damage household items, such as moth fur coat (Tinea pellionella), black skin bee eater (Anthrenus scrophularidae), or rhinothermids; and other parasites on domestic animals, such as fleas, lice or flies. Further, they are also effective against nematodes of plant pests, such as root growth nematodes, cyst nematodes, root nematodes, white rice nematodes (Aphelenchoides besseyi), strawberry bud nematodes (Nothotylenchus acris), or pine nematodes (Bursapheuslenchus lignon. Further, they are also effective against soil pests. These soil pests include gastropods, such as slugs or snails, or isopods, such as pillbugs or sowbugs. Among them, the compounds of the present invention are particularly effective against aphids, such as peach aphids or cotton aphids. Further, they are effective against harmful insects, such as aphids, which have become resistant to organophosphorus, carbamate and / or synthetic pyrethroid insectiids. Moreover, the compounds according to the present invention possess excellent systemic properties and when treating the soil with the compounds according to the present invention, not only harmful insects, harmful mites, harmful nematodes, harmful gastropods and harmful isopods in the soil are destroyed, but also harmful vegetation.

 When used as ingredients for insecticides, miticides, nematocytes or soil pesticides, the compounds of the present invention can be formulated together with agricultural additives to obtain various forms, such as dusts, granules, water dispersible granules, wettable powders, emulsifiable concentrates, suspension concentrates, soluble concentrates, water soluble powders, flowable compositions, aerosols or pastes, ultra small volume compositions and other similar agricultural products vein chemicals. When such compositions really find use, they are used as such or after dilution with suitable diluents, such as water, until a given concentration is obtained.

 Such compositions are usually prepared in 0.1-90 parts by weight. from the active ingredient and 10-99.9 parts by weight agricultural additives.

 As agricultural additives, mention may be made of carriers, emulsifiers, suspending agents, dispersants, extenders, penetration enhancers, wetting agents, thickeners or stabilizers. They can be added in each case as necessary. Carriers can be classified into solid and liquid carriers. As solid carriers, powders of animal and vegetable origin can be mentioned, such as starch, activated carbon, soy flour, wheat flour, wood flour or milk powder; or mineral powders such as talc, kaolin, bentonite, calcium carbonate, zeolite, diatomaceous earth, white carbon black, clay or alumina. As liquid carriers, water may be mentioned; alcohols such as isopropyl alcohol or ethylene glycol; ketones such as cyclohexanone or methyl ethyl ketone; esters such as dioxane or tetrahydrofuran; aliphatic hydrocarbons such as kerosene gas oil and the like; aromatic hydrocarbons such as xylene, trimethylbenzene, tetramethylbenzene, methylnaphthalene or solvent naphtha; halogenated hydrocarbons such as chlorobenzene; acid amides such as dimethylacetamide; esters such as glycerol ester of a fatty acid; nitriles such as acetonitrile; sulfur containing compounds such as dimethyl sulfoxide.

 Further, the compounds of the present invention can be used in combination with other agricultural chemicals, such as insecticides, miticides, nematicides, fungicides, antiviral agents, attractants, herbicides or plant growth regulators, as required in each case. In some cases, efficacy can be enhanced with such combinations.

 For example, the following may be mentioned as insecticides, miticides or nematicides.

Organic phosphate compounds:
O- (bromo-2-chlorophenyl) O-ethyl S-propyl phosphorothioate (common name: profenofos),
O- (2,2-dichlorvinyl) O, O-dimethylphosphate (common name: dichlorvos),
O-ethyl O- / 3-methyl-4- (methylthio) phenyl / N-isopropyl phosphoroamidate (common name: phenamiphos),
O, O-demityl O- (4-nitro-m-tolyl) phosphorothionate (common name: phenitrithione),
O-ethyl O- (4-nitrophenyl) phenyl phosphorothioate,
O, O-diethyl O- (2-isopropyl-6-methylpyrimidin-4-yl) phosphorothioate (common name: diazinon),
O, O-dimethyl O- (3,5,6-trichloro-2pyridyl) phosphorothioate (common name; Chlorpyrifos-methyl),
O, S-dimethyl N-acetylphosphoroamidothionate (common name: acephate),
O- (2,4-Dichlorophenyl) O-ethyl S-propyl phosphorodithioate (common name: prothiophos) and
(RS) -S-sec. -butyl O-ethyl 2-oxo-1,3-thiazolidin-3-yl phosphorothioate (common name: fostiazate).

Carbamate compounds:
1-naphthyl N-methylcarbamate (common name: carbaryl),
2-isopropylphenyl N-methyl carbomate (common name: propoxur),
2-methyl-2- (methylthio) propionaldehyde O-methylcarbamoyloxime (common name: aldicarb),
2,3-dihydro-2,2-dimethylbenzofuran-7-yl N-methylcarbamate (common name: carbofuran),
dimethyl N, N '- / thiobis / (methylimino) carbopyloxy // bisethanimidothioate (common name: thiodicarb),
S-methyl N- (methylcarbamoyloxy) thioacetamidate (common name: methomil),
N, N-dimethyl-2-methylcarbamoyloxyimino-2- (methylthio) acetamide (common name: oxamyl),
2- (ethylthiomethyl) phenyl N-methylcarbamate (common name: ethiophenecarb),
2-demythylamino-5,6-dimethylpyrimidin-4-yl N, N-dimethylcarbamate (common name: pyrimicarb) and
2-sec.-Butylphenyl N-methylcarbamate (common name: penobucarb).

Nereistoxin derivatives:
S, S'-2-dimethylaminotrimethylene bis (thiocarbamate) (common name: cartap) and
N, N-dimethyl-1,2,3-tritian-5-ylamine (common name: Thiocyclan).

Organochlorine compounds:
2,2,2-trichloro-1,1-bis (4-chlorophenyl) ethanol (common name: dicofol) and
4-chlorophenyl-2,4,5-trichlorophenylsulfone (common name: Tetradiphone).

Organometallic compounds:
Bis / Tris (2-methyl-2-phenylpropyl) tin / oxide (common name: phenbutatin oxide).

Pyrethroid compounds:
(RS) -α-cyano-3-phenoxybenzyl (RS) -2- (4-chlorophenyl) -3-methylbutylate (common name: phenvalerate),
3-phenoxybenzyl (IRS) -cis, trans-3- (2,2-dichlorvinyl) 2,2-dimethylcyclopropanecarboxylate (common name: permethrin),
(RS) -a-cyano-3-phenoxybenzyl (IRS) -cis, trans-3- (2,2-dichlorvinyl-2,2-dimethylcyclopropanecarboxylate (common name: cypermethrin),
(S) -a-cyano-3-phenoxybenzyl (IR) -cis-3- (2,2-dibromovinyl) -2,2-dimethylcyclopropanecarboxylate (common name: deltamethrin),
(RS) -a-cyano-3-phenoxybenzyl (IRS) -cis, trans-3- (2-chloro-3,3,3-trifluoropropenyl) -2,2-dimethylcyclopropanecarboxylate (common name: cygalotrin),
4-methyl-2,3,5,6-tetrafluorobenzyl-3- (2-chloro-3,3,3-trifluoro-1-propenyl) -2,2-dimethylcyclopropanecarboxylate (common name: Teflutrin) and
2- (4-ethoxyphenyl) -2-methylpropyl 3-phenoxybenzyl ether (common name: etofenprox).

Benzoylurea compounds:
1- (4-chlorophenyl) -3- (2,6-difluorobenzoyl) urea (common name: diflubenzuron),
1- / 3,5-dichloro-4- (3-chloro-5-trifluoromethyl-2-pyridyloxy) phenyl / -2 (2,6-difluorobenzoyl) urea (common name: chlorofluazuron) and
1- (3,5-dichloro-2,4-difluorophenyl) -3- (2,6-difluorobenzoyl) urea (common name: teflubenzuron).

Compounds similar to youthful hormone:
isopropyl (2E, 4E) 11 / methoxy-3,7,11-trimethyl-2,4-dodecadienoate (common name: methoprene).

Pyridazinone compounds:
2-t-butyl-5- (4-t-butylbenzylthio) -4-chloro-3 (2H) pyridazinone (common name: pyridaben).

Pyrazole compounds:
t-butyl 4 - / (1,3-dimethyl-5-phenoxypyrazol-4-yl) - methylene-amino-hydroxymethyl / benzoate (common name: fenpiroximate),
5-amino-1- (2,6-dichloro-a \, a, a-trifluoro-p-tolyl) -4-trifluoromethylsulfinylpyrazole-3-carbonitrile (common name: fipronil),
N - (4-tert.-Butylbenzyl) -4-chloro-3-ethyl-1-methylpyrazole-5-carboxamide (common name: tebufenpyrad).

Nitro compounds:
1- (6-chloro-3-pyridylmethyl) -N-nitro-imidazolidin-2-ylideneamine (common name: imidacloprid),
1- / N- (6-chloro-3-pyridylmethyl) -N-ethylamino / -1-methylamino-2-nitroethylene (common name: nitepiram),
N ¹ - / (6-chloro-3-pyridyl) methyl / -N ² -cyano-N ¹ -methyl acetamidine (European Patent Application Laid-Open No. 456826),
1- (6-chloro-3-pyridylmethyl) -2- (1-nitro-2-allylthioethylidene) imidazolidine (European Patent Application Laid-Open No. 437781),
1- (6-chloro-3-pyridylmethyl) -2- (1-nitro-2- (1-nitroethylthio-ethylidene) imidazolidene (European Patent Application Laid-Open No. 437781) and
1- (6-chloro-3-pyridylmethyl) -2- (1-nitro-2-b-methylallylthioethylidene) imidazolidine (European Patent Application Laid-Open No. 437781).

Hydrazine compounds:
N ¹ -t-butyl-N ¹ -3,5-dimethylbenzoyl-N-benzo / / 2-carbohydrazide,
N ¹ -t-butyl-N ¹ -3,5-dimethylbenzoyl-N-4,5,6,7-tetrahydrobenzo / b / thiophene-2-carbohydrazide,
N ¹ -t-butyl-N ¹ -3,5-dimethylbenzoyl-N-5,6-dihydro-4H-cyclopenta / b / thiophene-2-carbohydrazide and
N ¹ -t-butyl-N ¹ -3,5-dimethylbenzoyl-N-4-ethylphenylcarbohydrazide (common name: tebufenoside).

 Dinitro compounds.

 Organosulfur compounds.

 Urea compounds.

 Triazine compounds.

Other connections:
2-tert. -butylamino-3-isopropyl-5-phenyl-3,4,5,6-tetrahydro-2H-1,3,5-thiadiazin-4-one (common name: buprofesin),
trans- (4-chlorophenyl) -N-cyclohexyl-4-methyl-2-oxothiazolidinone-3-carboxamide (common name: hexithiazox),
N-methylbis (2,4-xylyliminomethyl) amine (common name: amitraz),
N ¹ - (4-chloro-o-tolyl) N, N-dimethylformamidine (common name: chlordimeform) and
(4-ethoxyphenyl) - / 3 / fluoro-3-phenoxyphenyl) propyl / (dimethyl) -silane (common name: silaflufen),
ethyl (3-tert.-butyl-1-1-methylcarbamoyl-1H-1,2,4-triazol-5-ylthio) acetate (common name: triazamate),
4,5-dihydro-6-methyl-4- (3-pyridylmethyleneamino) -1,2,4-triazin-3 (2H) -one (common name: pymetrozine),
5-chloro-N- / 2- / 4- (2-ethoxyethyl) -2,3-dimethylphenoxy / ethyl / -6-ethylpyramidin-4-amine (common name: Pyrimidiphene),
4-bromo-2- (4-chlorophenyl) -1-ethoxymethyl-5-trifluoromethylpyrrole-3-carbonitrile (Japanese Patent Publication, Unexamined, No. 104042/1989).

 The compound of the present invention may also be used in a mixture or combination with microbial agricultural chemicals such as B.T. and insect viruses, and antibiotics such as avermicin and milbemycin.

 Specific examples of the active ingredients of the above fungicides include the following compounds.

Pyrimidinamine compounds:
2-anilino-4-methyl-6- (1-propynyl) pyrimidine (disclosed in Japanese Examining Patent Publication No. 208581/1989).

Azole compounds:
1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -butanone (common name: triadimephone),
1- (biphenyl-4-yloxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -butan-2-ol (common name: bitertanol),
1- / N- (4-chloro-2-trifluoromethylphenyl) -2-propoxyacetimidoyl / imidazole (common name: triflumisole),
1- / 2- (2,4-dichlorophenyl) -4-ethyl-1,3-dioxolan-2-yl-methyl / -1H-1,2,4-triazole (common name: ethaconazole),
1- / 2- (2,4-dichlorophenyl) -4-propyl-1,3-dioxolan-2-yl-methyl / -1H-1,2,4-triazole (common name: propiconazole),
1- / 2- (2,4-dichlorophenyl) pentyl / -1H-1,2,4-triazole (common name: penconazole),
bis (4-fluorophenyl) (methyl) (1H-1,2,4-triazol-1-yl-methyl) -silane (common name: fluxilazole),
2- (4-4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl-methyl) hexane-nitrile (common name: myclobutanyl),
(2 RS, 3 RS) -2- (4-chlorophenyl) -3-cyclopropyl-1- (1H-1,2,4-triazol-1-yl) butan-2-ol (common name: cyproconazole),
(RS) -1- (4-chlorophenyl) -4,4-dimethyl-3- (1H-1,2,4-triazol-1-ylmethyl) pentan-3-ol (common name: terbukonazole),
(RS) -2 (2,4-dichlorophenyl) -1- (1H-1,2,4-triazol-1-yl) hexan-2-ol (common name: hexaconazole),
(2RS, 5RS) -5- (2,4-dichlorophenyl) tetrahydro-5- (1H-1,2,4-triazol-1-ylmethyl) -2-furyl 2,2,2-trifluoroethyl ether (common name: furconazole-cis) and
N-propyl-N- / 2- (2,4,6-trichlorophenoxy) ethyl / -imidazole-1-carboxamide (common name: prochlorase).

Quinoxaline compounds:
6-methyl-1,3-dithiolo- / 4,5-b / quinoxaline-2-one (common name: quinomethionate).

Dithiocarbamate compounds:
manganese ethylenebis (dithiocarbamate) polymer (common name: maneb),
zinc ethylenebis (dithiocarbamate) polymer (common name: cineb),
zinc complex with manganese ethylenebis (dithiocarbamate) (common name: mancozeb),
dizinc bis (dimethyldithiocarbamate) ethylenebis (dithiocarbamate) (common name: polycarbamate) and
zinc propylenebis (dithiocarbamate) polymer (common name: propineb).

Organochlorine compounds:
4,5,6,7-tetrachlorophthalide (common name: phthalide),
tetrachloroisophthalonitrile (common name: chlorophthalinyl) and
pentachloronitrobenzene (common name: Chintosene).

Benzamidazole compounds:
methyl 1- (butylcarbamoyl) benzimidazol-2-ylcarbamate (common name: benomyl),
dimethyl 4.4 '- (o-phenylene) bis (3-thioallophanate) (common name: thiophanate-methyl) and
methyl benzimidazol-2-ylcarbamate (common name: carbendazim).

Pyridinamine compounds:
3-chloro-N- (3-chloro-2,6-dinitro-4-a, α, α-trifluorotolyl) -5-trifluoromethyl-2-pyridinamine (common name: fluazinam).

Cyanoacetamide compounds:
1- (2-cyano-2-methoxyiminoacetyl) -3-ethylurea (common name: cymoxanyl).

Phenylamide compounds:
methyl N- (2-methoxyacetyl) -N- (2,6-xylyl) -D, L-alaninate (common name: metalaxyl),
2-methoxy-N- (2-oxo-1,3-oxazolidin-3-yl) aceto-2 ', 6'-xididide (common name: oxadixyl),
(±) -a-2-chloro-N- (2,6-xylylacetamido) -g-butyrolactone (common name: Ofurats),
methyl V-phenylacetyl-N- (2,6-xylyl) -DL-alinate (common name: vanalaxyl),
methyl N- (2-furoyl) -N- (2,6-xylyl) -DL-alaninate (common name: furalaxyl) and
(±) -a- / N- (3-chlorophenyl) cyclopropanecarboxamido / -g-butyrolactone (common name: ciprofuram).

Sulfonic acid compounds:
N-dichlorofluoromethylthio-N ', N'-dimethyl-N-phenylsulfamide (common name: dichlorofluanide).

Copper connections:
copper (II) hydroxide (common name: copper hydroxide),
(8-quinolinolate of copper (common name: oxine-copper).

Isoxazole compounds:
5-methylisoxazol-3-ol (common name: hydroxyisoxazole).

Organophosphorus compounds:
aluminum tris (ethyl phosphonate) (common name: fosetil-al),
0,2,6-dichloro-n-tolyl-0,0-dimethylphosphorothioate (common name: tolkofos-methyl),
S-benzyl 0,0-diisopropyl phosphorothioate,
O-ethyl S, S-diphenyl phosphorodithioate and aluminum acid ethylphosphonate.

N-halogenoalkyl compounds:
N- (trichloromethylthio) cyclohex-4-en-1,3-dicarboximide (common name: captan),
N- (1,1,2,2-tetrachloroethylthio) cyclohex-4-en-1,2-dicarboximide (common name: captofol) and
N- (trichloromethylthio) phthalimide (common name: folpet).

Dicarboximide compounds:
N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide (common name: procymidone),
3- (3,5-dichlorophenyl-N-isopropyl-2,4-dioxoimidazolidine-1-carboxamide (common name: iprodion) and
(RS) -3- (3,5-dichlorophenyl) -5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione (common name: vinclozolin).

Benzanilide compounds:
a, a, a-trifluoro-3'-isopropoxy-o-toluanilide (common name: flutolanil) and
3'-isopropoxy-o-toluanilide (common name: mepronil).

Benzamide compounds:
2- (1,3-dimethylpyrazol-4-ylcarbonylamino) -4-methyl-3-pentennitrile (disclosed in British Patent No. 2,190,375) and
a- (nicotinylamino) - (3-fluorophenyl) acetonitrile (disclosed in Japanese Patent Application Laid-Open No. 135364/1988).

Piperazine compounds:
N, N '- / piperazine-1,4-diylbis (trichloromethyl) methylene / -formamide (common name: triforin).

Pyridine compounds:
2 ', 4'-dichloro-2- (3-pyridyl) acetophenone 0-methyloxime (common name: pyrifenox).

Carbinol compounds:
(±) -2,4'-dichloro-a- (pyrimidin-5-yl) benhydrol alcohol (common name: phenarimol) and
(±) -2,4'-difluoro-a- (1H-1,2,4-triazol-1-ylmethyl) benzhydryl alcohol (common name: flutriafol).

Piperidine compounds:
(RS) -1- / 3- (4-tert.-Butylphenyl) -2-methylpropyl / piperidine (common name: fenpropidin).

Morpholine compounds:
(±) -cis-4- / 3- (4-tert.-Butylphenyl) -2-methylpropyl / -2,6-dimethylmorpholine (common name: fenproimorph).

Organotin compounds:
triphenyltin hydroxide (common name: fentin hydroxide) and
triphenyltin acetate (common name: fentin acetate).

Urea compounds:
1- (4-chlorobenzyl) -1-cyclopentyl-3-phenylurea (common name: pencisuron).

Compounds of cippamic (cinnamic) acid:
(E) 4- / 3 (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) acryloyl / -morpholine (common name: dimethophore).

Phenylcarbamate compounds:
isopropyl 3,4-diethoxycarbonylate (common name: diethoxycarbonate).

Cyanpyrrole compounds:
3-cyan-4- (2,2-difluoro-1,3-benodioxol-4-yl) -pyrrole) (common name: safir) and
3- (2 ', 3'-dichlorophenyl) -4-cyanopyrrole (common name: fenpiclonil).

Pyridinamine compounds:
3-chloro-V- (3-chloro-2,6-dinitro-4-a, a, a-trifluorotolyl) -5-trifluoromethyl-2-pyridinamine (common name: fluazinam).

Other active fungicide ingredients include anthrachine compounds, crotonic acid compounds, antibiotics, and other compounds such as:
1,3-dithiolan-2-ylidene-malonic acid diisopropyl ester (common name: isoprothiolan),
5-methyl-1,2,4-triazolo / 3,4-b / benzothiazole (common name: tricyclozole),
1,2,5,6-tetrahydropyrrolo / 3,2,1-ij / quinolin-4-one (common name: pyrochilone),
6- (3,5-dichloro-4-methylphenyl) -3 (2H) -pyridazinone (common name: diclomesine),
3-allyl-hydroxy-1,2-benzothiazole-1,1-dioxide (common name: probepazole).

 A suitable weight ratio of the compound of the present invention to other agricultural chemicals when mixed, when used in a mixture or combination, can generally be in the range of 1: 300 to 300: 1, preferably in the range of 1: 100 to 100: 1.

 Pesticides in accordance with the present invention are used at a concentration of the active ingredient from 0.1 to 500,000 ppm, preferably from 1 to 100,000 ppm. The concentration of the active ingredient can be arbitrarily changed depending on the formulation, method, purpose, time or place of use and the condition of insect pests. For example, aquatic pests can be eliminated by applying a formulation having the aforementioned concentration to the flash point and thus the concentration of the active ingredient in the water is less than the aforementioned limits.

 The amount of active ingredient applied per unit surface area is usually from about 0.5 to 5000 g, preferably from 10 to 1000 g per hectare. However, in certain special cases, this amount may go beyond the specified limits.

 Various formulations containing the compounds of the present invention or diluted compositions thereof may be applied by methods conventionally used for this purpose, such as spraying (i.e. spraying, spraying, fogging, spraying, dispersing a powder or grains or dispersing in water) application to the soil (i.e., mixing or impregnation), application to the surface (i.e., coating, powder or coating) or impregnation to produce poisoned feed. Further, it is possible to feed domestic animals with food containing the above active ingredient and control the outbreak or increase in the number of pests, especially insects, using animal excrement. Further, the active ingredient can be applied by the so-called ultra-small volume method. With this method, the composition can be 100% composed of the active ingredient.

 Further, the use of pesticides in accordance with the present invention includes, in addition to their direct application to pests, any other application in which the amide compounds of formula (1) or their salts act on pests. As such another application, a case may be mentioned in which other effective compounds decompose into amide compounds of formula (1) in an environment such as soil, which will then act on pests.

 Below the present invention will be described with reference to examples. However, it should be understood that the present invention is in no way limited to these specific examples.

 Synthesis Example 1. Preparation of N-cyanomethyl-4-trifluoromethyl-3-pyridinecarboxamide (compound N1).

A solution of 0.96 g of 4-trifluoromethyl-3-pyridinecarboxylic acid and 1.19 g of thionyl chloride in 5 ml of benzene was heated under reflux for 30 minutes in the presence of a catalytic amount of dimethylformamide. Excess thionyl chloride and benzene were distilled off under reduced pressure. Then, the residue was dissolved in 15 ml of tetrahydrofuran. Thereafter, 1.82 g of triethylamine and 1.05 g of aminoacetonitrile sulfate were added thereto, and the mixture was stirred at room temperature for 18 hours. The mixture was then poured into water and extracted with ethyl acetate. The organic layer was washed with an aqueous solution of ammonium chloride, water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.50 g of the desired product (compound N1) having a melting point of 155 to 161 ^° C.

 Synthesis Example 2. Preparation of N-allyl-4-trifluoromethyl-3-pyridinecarboxamide (compound N 22).

A solution of 0.26 g of 4-trifluoromethyl-3-pyridinecarboxylic acid and 0.24 g of thionyl chloride in 10 ml of benzene was heated under reflux for 30 minutes in the presence of a catalytic amount of dimethylformamide. Excess thionyl chloride and benzene were distilled off under reduced pressure. Then the residue was dissolved in 15 ml of tetrahydrofuran. Thereafter, 0.21 triethylamine and 0.12 g of allylamine were added thereto, and the mixture was stirred at room temperature for 20 hours. The mixture was then poured into an aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.21 g of the desired product (compound N 22) having a melting point of 75.5 to 77 ^° C.

 Synthesis Example 3. Preparation of 4-trifluoromethyl-3-pyridinecarboxamide (compound N 5).

A solution comprising 3 g of 4-trifluoromethyl-3-pyridinecarboxylic acid, 6.7 ml of thionyl chloride and 20 ml of benzene was heated under reflux for 1.5 hours in the presence of a catalytic amount of dimethylformamide. Excess thionyl chloride and benzene were distilled off. Then the residue was dissolved in 5 ml of ethyl acetate. This solution was gradually added dropwise to 20 ml of ammonia while cooling with ice. After dropping the solution, the mixture was stirred at room temperature for 30 minutes. Then water and ethyl acetate were distilled off under reduced pressure. The residue was extracted with heated ethyl acetate to give 2.1 g of 4-trifluoromethyl-3-pyridinecarboxamide (melting point: 162.7 ^° C.) as the desired product.

 Synthesis Example 4. Preparation of 4-trifluoromethyl-3-pyridinecarboxamide (compound N 5).

(1) 11.3 g of 3-cyano-2,6-dichloro-4-trifluoromethylpyridine was gradually added to 22.6 ml of concentrated sulfuric acid, then the mixture was heated and allowed to react for 1 h at 100 ^o C. After completion of the reaction, the mixture was poured into ice water, after which a white precipitate formed. The precipitate was collected on a filter, and the filtrate was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain a white solid. This solid and the previously obtained precipitate were combined to give 9.2 g of 2,6-dichloro-4-trifluoromethyl-3-pyridicarboxamide.

 (2) 9.2 g of 2,6-dichloro-4-trifluoromethyl-3-pyridinecarboxamide obtained in step (1) (see above), 0.66 g of 10% palladium carbon and 6.4 g of anhydrous sodium acetate added to 200 ml of methanol. Then, a reduction reaction was carried out under a hydrogen atmosphere at room temperature for 12 hours. After the reaction, the reduction catalyst was removed with celite, and the filtrate was concentrated. Extraction was performed by adding ethyl acetate and water to the precipitate. The organic layer was dried over anhydrous sodium sulfate. The solvent was then distilled off, yielding 5.2 g of 4-trifluoromethyl-3-pyridinecarboxamide as the desired product.

 Synthesis Example 5. Obtaining ethyl 4-trifluoromethylnicotinoylaminoacetimidate (compound N 32).

 5 ml of absolute ethanol was placed in an ice-cooled flask such as a Kjeldahl flask and 100 mg (0.4 mmol) of 4-trifluoromethyl-N- (cyanomethyl) -3-pyridicarboxamide was added to it. After the mixture was allowed to absorb hydrogen chloride, the flask was sealed and left to stand in the refrigerator for 21 hours. Then the mixture was returned to room temperature and subjected to distillation under reduced pressure, followed by drying under vacuum.

The hydrochloride thus obtained was added to an aqueous solution of sodium hydrogencarbonate and thus neutralized. Then it was extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate 3/7) to obtain 0.165 g (yield: 45.8%) of ethyl 4-trifluoromethylnioiothinylamide having a melting point of 64.5 to 66.0 ^o C.

 Synthesis Example 6. Preparation of O-methyl N- (4-trifluoromethylnicotinoylthiocarbamate (compound No. 9).

 1.12 g (11 mmol) of potassium thiocyanate is added to 30 ml of benzene and then 2.19 g (10 mmol) of 4-trifluoromethyl nicotinic acid are added dropwise at room temperature. The mixture was then refluxed for 6 hours. After refluxing, the mixture was distilled under reduced pressure to give 4-trifluoromethyl nicotinoylthioisocyanate.

The thioisocyanate thus obtained was added to 30 ml of acetonitrile and 0.44 ml (10.5 mmol) of methanol was added dropwise to it. The mixture was stirred at room temperature for 16 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with an aqueous sodium solution and then concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate 6/4) to obtain 0.84 g (yield: 30.4%) of O-methyl N- (4-trifluoromethylnicotinoyl) thiocarbamate having a point melting from 138 to 141.5 ^o C.

 Synthesis Example 7. Preparation of O-methyl S-methyl N- (4-trifluoronicotinoyl) iminothiocarbonate (compound No. 14).

 To a solution containing 0.200 g (0.78 mmol) of O-methyl N- (4-trifluoromethylnicotinoyl thiocarbamate obtained in Example 6 above and 2 ml of dimethylformamide was added at room temperature, 0.034 g (0.85 mmol) was added. 15 minutes and then 0.118 g (0.83 mmol) of methyl iodide was added dropwise, the mixture was stirred at room temperature for one hour, then poured into water and extracted with ethyl acetate.The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. and concentrated under reduced pressure The residue thus obtained was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate 7/3) to obtain 0.133 g (yield: 63.1%) of an oily O-methyl S-methyl N- ( 4-trifluoromethyl nicotinoyl) iminocarbonate.

 Synthesis Example 8. Preparation of N- (N'-isopropylaminomethyl) -4-trifluoromethylpyridine-3-carboxamide (compound N 4).

In 30 ml of dimethoxyethane, 0.6 g of hydrogen chloride gas was passed at 20 ^° C. Then this solution was cooled to -30 ^o C. Then a solution containing 0.72 g (3.4 mmol) of 1, 3, 5-triisopropyl-2, 4, 6-hexahydrotriazine dissolved in 5 ml of dimethoxyethane was added dropwise to it. 1.88 g (9.9 mmol) of trifluoromethylpyridin-3-carboxamide were added.

This solution was stirred at room temperature for 12 hours. Then, the solvent was distilled off under reduced pressure. The residue was dissolved in 30 ml of methanol, and then 3 g (30 mmol) of triethylamine were added to it. Methanol was distilled off under reduced pressure, and then 30 ml of ethyl acetate was added thereto. After this, the impurities were filtered off, the filtrate was concentrated and purified by silica gel column chromatography (eluent: ethyl acetate / ethanol 85/15) to obtain 1.1 g (yield: 42.6%) N- (N ¹ -isopropylaminomethyl) -4- trifluoromethylpyridine-3-carboxamide having a melting point of 119.8 ^° C. as the desired product.

Synthesis Example 9. Preparation of N- (N ¹ , N ¹ -dimethylaminomethyl) -4-trifluoromethylpyridin-3-carboxamide (compound N 11).

To a mixed solution containing 1.3 g (6.8 mmol) of 4-trifluoromethylpyridin-3-carboxamide, 1.5 ml of water and 0.63 g (7 mmol) of dimethylamine, 37% was added 37% aqueous formaldehyde solution. The mixture was then allowed to react for two hours at 80 ^° C. After completion of the reaction, anhydrous sodium carbonate was added to the reaction solution until it was saturated. Then methylene chloride and water were added to it and extraction was performed. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (eluent, ethyl acetate / methanol 19/1) to obtain 0.55 g (yield: 32.5%) N- (N ¹ , N ¹ -dimethylaminomethyl) -4 trifluoromethylpyridine-3-carboxamide (melting point: 50 58 ^° C) as the desired product.

 Synthesis Example 10. Preparation of 4-trifluoromethyl-3-pyridinecarboxamide 1-oxide (compound N 111).

0.8 g of 4-trifluoromethyl-3-pyridinecarboxamide was dissolved in 7 ml of acetic acid. Then, 0.72 g of a 30% aqueous solution of hydrogen peroxide was gradually added dropwise to it. After the completion of the dropping, the reaction solution was heated to 70 ^° C and stirred for 8 hours at this temperature. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue thus obtained was washed with n-hexane to obtain 0.6 g of 1-oxide 4-trifluoromethyl-3-pyridinecarboxamide (melting point 198.8 ^° C.) as the desired product.

 The compounds of formula (1) obtained in accordance with the present invention are shown in the table.

The compounds of formula (1) also include the following compounds:
compound N 124: 4-chlorodifluoromethyl-3-pyridinecarboxamide,
compound N 125: 4-dichlorofluoromethyl-3-pipridinecarboxamide,
compound N 126: 4-trichloromethyl-3-pyrindicarboxamide,
compound N 127: 4-difluoromethyl-3-pyridinecarboxamide,
compound N 128: 4-fluoromethyl-3-pyridinecarboxamide,
compound N 129: 4-b, b, b-trifluoroethyl-3-pyridinecarboxamide,
compound N 130: 4-pentafluoroethyl-3-pyridinecarboxamide,
compound N 131: 4-dibromomethyl-3-pyridinecarboxamide (mp 115-117.5 ^° C),
compound N 132: 4-bromomethyl-3-pyridinecarboxamide.

 Test Example 1. Insecticidal test against peach aphids (Murus persicae).

Насекомые, отпавшие от листа, считались мертвыми.Each composition containing the active ingredient was dispersed in water to obtain a dispersion of each active ingredient at a concentration of 800 ppm. A petiole of each eggplant with only one remaining leaf (planted in a pot having a diameter of 8 cm and a height of 7 cm) was provided with a sticker, and about 2 3 wingless viviparous female peach aphids (Murus persicae) were planted and incubated on each leaf. Two days after infection, adult insects were removed and the number of larvae was counted. Then the leaf of the eggplant plant infected with the larvae was immersed in the above-prepared dispersion having a predetermined concentration of about 10 s, then it was dried in air and kept in a light chamber with a constant temperature of 26 ^o C. On the 5th day after the treatment, dead insects were counted and determined mortality according to the following equation:

Insects falling from the leaf were considered dead.

 As a result, mortality was 100% with each compound NN 1-56, 58-66, 69, 70, 72-79, 82, 85-89, 91, 99 and 102-111, and from 90 to 99% with compounds NN 57 , 67, 68, 71 and 80.

 Test Example 2. Systemic test against peach aphids (Murus persicae).

Each composition containing the active ingredient was dispersed in water to obtain a dispersion of each active ingredient at a concentration of 800 ppm. A petiole of each of the eggplant plants with only one remaining leaf (planted in a pot with a diameter of 8 cm and a height of 7 cm) was provided with a sticker and approximately 2 plants were planted and incubated on each leaf of the eggplant
3 wingless viviparous females of a peach aphid (Murus persicae). Two days after infection, adult insects were removed and the number of larvae was counted. Then the eggplant plant infected with the larvae was treated by soaking the soil in a pot with 10 ml of the above prepared dispersion, which had a given concentration, and kept in a light chamber with a constant temperature of 26 ^o C. Dead insects were counted every 5th day after the treatment, and mortality was determined by in the same manner as in test example 1.

 The mortality as a result was 100% with each of the compounds NN 1-17, 20-23, 26-28, 30, 31, 33-37, 39-41, 44, 46, 49, 50, 78, 85, 86, 88 89, 99, 103, 104 and 111.

 Test Example 3. System Test Against Thirps palmi.

Each composition containing the active ingredient was dispersed in water to obtain a dispersion of each active ingredient at a concentration of 800 ppm. The petiole of each eggplant with only one remaining leaf (planted in a pot with a diameter of 8 cm and a height of 7 cm) was provided with a sticker, and approximately 20 adult Thirps palmi insects were planted on each leaf of the eggplant. One day after infection, an eggplant infected with adult insects was treated by soaking the soil in a pot in ml of the above dispersion having a given concentration and kept in a light chamber with a constant temperature of 26 ^o C. On the 8th day after treatment, the number of parasitic adults was counted next generation insects and larvae.

 There were 4 adult insects and 172 larvae on the untreated eggplant. In contrast, no adult insects were found on the eggplant plant treated with compounds NN 1, 5 and 85, indicating a high insecticidal efficacy.

 The following are examples of formulations according to the present invention. However, these specific examples do not limit the compounds of the present invention, amounts of active ingredients or types of formulations.

 Formulation Example 1, parts by weight

(a) compound N 1 20
(b) kaolin 72
(c) sodium ligninsulfonate 8
The above components were uniformly mixed to obtain a wettable powder.

 Formulation Example 2, parts by weight

(a) compound N 4 5
(b) talcum 95
The above components were uniformly mixed to obtain dust.

 Formulation Example 3, parts by weight

(a) compound N 2 20
(b) N, N'-dimethylacetamide 20
(c) polyoxyethylene alkyl phenyl ether 10
(g) xylene 50
The above components were uniformly mixed and dissolved to obtain an emulsifiable concentrate.

 Formulation Example 4, parts by weight

(a) kaolin 68
(b) sodium ligninsulfonate 2
(c) polyoxyethylene alkyl aryl sulfate 5
(g) fine silica powder 25
A mixture of the above components is mixed with compound N 5 in a weight ratio of 4: 1 to obtain a wettable powder.

 Formulation Example 5, parts by weight

(a) compound N 12 50
(b) oxylated polyalkylphenyl phosphate triethanolamine 2
(c) silicone 0.2
(g) water 47.8
The above components were uniformly mixed and ground into a powder to obtain a liquid carrier, and added, parts by weight

(d) sodium polycarboxylate 5
(e) anhydrous sodium sulfate 42.8
and the mixture was uniformly mixed and dried to obtain water dispersible granules.

 Formulation Example 6, parts by weight

(a) compound N 85 5
(b) polyoxyethylene octyl phenyl ether 1
(c) phosphoric acid polyoxyethylene ester 0.5
(g) granular calcium carbonate 93.5
The above components (a) (c) were uniformly mixed and plasticized together with a small amount of acetone, and then the mixture was sprayed onto component (g) to remove acetone, thereby obtaining granules.

 Formulation Example 7, parts by weight

(a) compound N 16 2.5
(b) N-methyl-2-pyrrolidone 2.5
(c) soybean oil 95.0
The above components were uniformly mixed and dissolved to obtain an ultra-small volume composition.

 Formulation Example 8, parts by weight

(a) compound N 3 5
(b) N, N ¹ -dimethylacetamide 15
(c) polyoxyethylene alkyl aryl ether 10
(g) xylene 70
The above components were uniformly mixed to obtain an emulsifiable concentrate.

 Formulation Example 9, parts by weight

(a) compound N 111 20
(b) sodium lauryl sulfate 3
(c) water soluble starch 77
The above components were uniformly mixed to obtain a water-soluble powder.

Claims (10)

1. Derivatives of pyridine of General formula I

where X is oxygen or sulfur;
R ^{1 is} hydrogen, lower alkyl which may be substituted with a group of cyano, trifluoromethyl, cyclopropyl, hydroxy, lower alkoxy, lower alkoxycarbonyl, lower alkylcarbonyloxy, phenoxy, formyl, acetyl, benzoyl, (lower alkyl) thio, amido, thioamido, N- ( lower alkyl) amido, mono (lower alkyl) amino, di (lower alkyl) amino, trifluoromethylpyridylcarbonyloxy, trifluoromethylpyridylcarbonylamino, phenyl (which may be substituted with lower alkyl, lower alkoxy, halogen, nitro, trifluoromethyl or 4-methylthiomethyl) 4-methylthio ) sulfonyl, amidino, ethyl imidate, irrolidino, piperidino, morpholino (which may be substituted on the ring lower alkyl groups) or piperazino substituted at the second ring nitrogen atom by lower alkyl or phenyl, lower alkenyl, lower alkynyl, C ₃ -C ₆ - cycloalkyl radical, or R ¹ -C ( W ') R ³ , where W ^{1 is} oxygen or sulfur, R ^{3 is} lower alkyl, lower alkoxy, (lower alkyl) thio or (lower alkyl) amino, SO ₂ R ⁴ , where R ^{4 is} lower alkyl or di (lower alkyl) amino , NHR ⁵ , where R ⁵ is 2-pyridyl;
R ² hydrogen, lower alkyl, which may be substituted by lower alkoxy or (lower alkyl) carbonyloxy, group

where R ^{3 ′} is lower alkyl, lower alkoxy, (lower alkyl) thio or trifluoromethylpyridyl, or the group —SO ₂ R ^{4 ′} , where _R 4 ′ _is lower alkyl;
either R ¹ and R ² taken together form a group C (R ⁶ ) R ⁷ , where R ⁶ and R ⁷ independently from each other are lower alkoxy, (lower alkyl) thio or R ¹ and R ² together with the nitrogen atom form a morpholine ring, 4- (lower alkyl) piperazine ring or 2-cyanimino-3-methyl-1,3-diazolidine ring;
m 0 or 1, provided that when m 0 and X are oxygen, R ¹ and R ² are not simultaneously hydrogen.  2. Derivatives of pyridine according to claim 1, characterized in that X is oxygen. 3. The pyridine derivatives according to claim 1, characterized in that R ^{1 is} hydrogen, lower alkyl, which may be substituted by cyano, trifluoromethyl, cyclopropyl, hydroxy, lower alkoxy, lower alkoxycarbonyl, lower alkylcarbonyloxy, phenoxy, formyl, acetyl, benzoyl , (lower alkyl) thio-, amido-, thioamido-, N- (lower alkyl) amido-, mono (lower alkyl) amino, di (lower alkyl) amino, trifluoromethyl pyridylcarbonyloxy, trifluoromethylpyridylcarbonylamino, phenyl, which may be substituted, lower alkyl, lower alkoxy, halogen, nitro group, trifluoromethyl or 4-methylthiophenoxy group, (lower alkyl) sulfonyl, amidino, ethylimidate, pyrrolidino, piperidino, morpholino groups (which may be substituted in the nucleus with lower alkyls) or the piperazine atom of the nucleus of the lower atom of the second atom substituted or phenyl or a group C (W ') R ³ , where W' is oxygen or sulfur, and R ^{3 is} lower alkyl, lower alkoxy, R ² hydrogen, lower alkyl, which may be substituted by lower alkoxy or (lower alkyl) -carbonyloxy or group

where R ^{3 ′} lower alkyl, lower alkoxy group, (lower alkyl) thio group or trifluoromethylpyridyl, or R ¹ and R ² together form a group C (R ⁶ ) R ⁷ where R ⁶ and R ⁷ independently represent lower alkoxy or lower alkylthio group. 4. The pyridine derivatives according to claim 1, characterized in that X is oxygen, R ^{1 is} hydrogen, lower alkyl, lower alkoxyalkyl, lower alkylaminoalkyl, di (lower alkyl) aminoalkyl, piperidinoalkyl, lower hydroxyalkyl, lower cyanoalkyl, thiocarbamoylalkyl, lower alkylcarbonyloxyalkyl alkylcarbonyl, lower alkoxythiocarbonyl or lower alkoxycarbonyl, R ² hydrogen, lower alkyl, lower alkoxyalkyl, lower alkylcarbonyloxyalkyl, lower alkylcarbonyl, trifluoromethylpyridylcarbonyl or lower alkoxycarbonyl or R ¹ and R ² together form a group C (R ⁶ ) ⁷ , where R ⁶ and R ⁷ are a lower alkoxy group or a lower alkylthio group.  5. The pyridine derivatives according to claim 1, characterized in that said compound is 4-trifluoromethyl-3-pyridinecarboxamide-1-oxide, or N-cyanomethyl-4-trifluoromethyl-3-pyridinecarboxamide, N-thiocarbamoylmethyl-4-trifluoromethyl- 3-pyridinecarboxamide, N-ethoxymethyl-4-trifluoromethyl-3-pyridinecarboxamide, N-isopropylamino-methyl-4-trifluoromethyl-3-pyridinecarboxamide, N-cyanomethyl-N, N-bis- (4-trifluoromethylnicotinoyl) amine, -N - cyanomethyl-4-trifluoromethyl-3-pyridinecarboxamide, N-cyanomethyl-N-methyl-4-trifluoromethylpyridin-3-carboxamide, O-methyl-N- (4-trifluoromethyl nicotinoyl) thiocarbamate, N-methyl-4-trifluoromethylpyridine-3-carboxamide, N- (N ', N'-dimethylaminomethyl) -4-trifluoromethylpyridin-3-carboxamide, N- (1-piperidinylmethyl) -4-trifluoromethylpyridin-3- carboxamide, N-cyanomethyl-N- (4-trifluoromethylnicotinoyl) aminomethyl pivalate, O, S-dimethyl-N- (4-trifluoromethylnicotinoyl) iminoformate, N-hydroxymethyl-4-trifluoromethyl-3-pyridinecarboxamide, N-acetyl-4-trif 3-pyridinecarboxamide or methyl N- (4-trifluoromethylnicotinoyl) carbamate or 1-oxide of these compounds. 6. The method of obtaining pyridine derivatives of General formula II

where R ¹ and R ² have the values according to claim 1 and can be simultaneously hydrogen, characterized in that the reaction of 4-trifluoromethylpyridin-3-carboxylic acid or its reactive derivative with a compound of General formula III
HN (R ¹ ) R ² ,
where R ¹ and R ² have the indicated meanings.  7. An insecticidal composition containing, as an active component, a pyridinecarboxamide derivative and suitable additives, characterized in that, as said pyridinecarboxamide derivative, it contains a compound of formula I according to claim 1, or 4-trifluoromethyl-3-pyridinecarboxamide, in an insecticidally effective amount.  8. The composition according to claim 7, characterized in that the active component is 4-trifluoromethyl-3-pyridinecarboxamide, N-cyanomethyl-4-trifluoromethyl-3-pyridinecarboxamide, N-thiocarbomoylmethyl-4-trifluoromethyl-3-pyridinecarboxamide, N-ethoxymeth -4-trifluoromethyl-3-pyridinecarboxamide, N-isopropylaminomethyl-4-trifluoromethyl-3-pyridinecarboxamide, N-cyanomethyl-N, N-bis (4-trifluoromethylnicotinoyl) amine, N-acetyl-N cyanomethyl-4-trifluoromethyl-3 pyridinecarboxamide, N-cyanomethyl-N methyl-4-trifluoromethyl pyridine-3-carboxamide, O-methyl-N- (4-trifluoromethylnicotinoyl) thiocarbamate, N-methyl-4-t rifluoromethylpyridine-3-carboxamide, N (N ', N'-dimethylaminomethyl) -4-trifluoromethylpyridin-3-carboxamide, N- (1-piperidinyl) -4-trifluoromethylpyridine-3-carboxamide, N-cyanomethyl-N- (4- trifluoromethylnicotinoyl) aminomethyl pivalate, O, S-dimethyl-N- (4-trifluoromethylnicotinoyl) iminoformate, N-hydroxymethyl-4-trifluoromethyl-3-pyridinecarboxamide, N-acetyl-4-trifluoromethyl-3-pyridinecarboxamide (4-methyl trifluoromethyl nicotinoyl) carbamate or its 1-oxide.  9. The composition according to claim 7, characterized in that the active component is 4-trifluoromethyl-3-pyridicarboxamide or its 1-oxide. Point priority
03/17/93 according to claims 1-8.  02/05/93 according to claim 9.

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