MXPA99001261A

MXPA99001261A - Process for the preparation of compounds of 2-aril-5- (perfluoroalquil) pirrol from compounds n- (arilmetilen) -1-chlorine-1- (perfluoroalquil) metilam

Info

Publication number: MXPA99001261A
Application number: MXPA/A/1999/001261A
Authority: MX
Inventors: Kameswaran Venkataraman
Original assignee: American Cyanamidcompany
Priority date: 1998-02-09
Filing date: 1999-02-03
Publication date: 2000-10-01

Abstract

A process for the preparation of 2-aryl-5- (perfluoroalkyl) pyrrole compounds from compounds N- (arylmethylene) -1-chloro-1- (perfluoroalkyl) methylamino is presented. The 2-aryl-5- (perfluoroalkyl) pyrrole compounds are useful for combating insect pests and mites, and can also be used to prepare other pesticidal arylpyrrole compounds. In addition, the present invention features N- (arylmethylene) -1-chloro-1- (perfluoroalkyl) methylamine compounds which serve as intermediates in the preparation of the arylpyrrrrrrrrrrrr

Description

PROCESS FOR THE PREPARATION OF COMPOUNDS OF 2-ARIL-5- (PERFLUOROALQUIL) PIRROL FROM COMPOUNDS N- (ARYLMETILEN) -1-CHLORO-1 - (PERF? _UOROALQUIL) METHYLAMINE BACKGROUND OF THE INVENTION Compounds 2-ar? L -5- (perfluoroalkyl) pyrol are useful as pesticides and acaricides Aaemas these compounds also serve for the preparation of other insecticide and acaricide agents Specifically, the compounds 2-ar? L-5- (perfluoroalqu l) For this reason, there is a constant search to discover new and efficient methods for the preparation of compounds 2-apl-5 (perfluoroalkyl) p? rr? ? US Pat. No. 5,154,986 describes that compounds of 2 api-5- (tr.) Methyl can be prepared from 5-ccru or 5-ccru - (cenalo sustttu? ao) -2 2 2-tr? fluoroacet? m? do? it La? Patents of the Unique Stats Nos. 5 446 1? 0 ^ 5 235 225 describe that -nc-estcs 2-api-5- can be obtained. { tr? nuoromet ?! I would like to make a few steps to parish the village. The processes described in the patents 5 445 1 705 and 5 235 225 refer to the use of an asynchronous landfill. obtains by means of the 0 yes thesis Strec < However, the résistance of the Strecker synthesis is not entirely satisfactory because of the erosion currents with ae content. Therefore, what is needed in the technique is an efficient process. process for the preparation of 2-ar? i-5- (periuorocol) compounds that does not require the use of N-chloride compounds. -2.2.2- t .-? R.uo'oaceto? M? Ao ?? and avoid the use of Strecker synthesis It is also an objective of the present invention to present a new D'o that will give the ceoaraaon Pe compounds aplpirrol such as chlorphepapir REF. 29315 Another objective of the present invention is to present new intermediates which serve for the processes described below.

These and other objects of the present invention will become apparent in the light of the detailed description thereof which is set forth below. SUMMARY OF THE INVENTION The present invention presents an efficient process for the preparation of 2-apl-5- (perfluoroalkyl) pyrrol compounds having the formula I (I) in which W is hydrogen 0 CmF2m *? . R is alkyl C1.C4 ^ each of m and n is independently an integer of 1, 2. 3 4. 5. 6. 7 u L is hydrogen or halogen. each of M and Q is independently hydrogen, halogen, CN, NO2, C1.C4 alkyl. haloalkyl C1.C4 alkoxy C1.C4, haloalkoxy C1.C4, alkylthio C? .C4; haloalkylthio C1.C4. C 1 -C 4 alkylsulfamyl. C1-C4 haloalkylsulfinyl, alkylsulfoniium Ci. C4 haloalkylsulfomyl C1.C4. or. when M and Q are in adjacent positions, they can be taken together with the carbon atoms to which they are attached to form a ring in which MQ represents the structure -OCH2O-, -OCF2O- or -CH = CH-CH = CH -; R ,, R2 and R3 are, independently, hydrogen, halogen, NO2, CHO or R2 and R3 can be taken together with the atoms to which they are attached to form a ring in which R2R3 is represented by the structure each of R4, R5, R6 and R7 is independently hydrogen, halogen, CN or N02 and X is O or S process consisting of reacting a compound N- (arylmethylene) -1-c! gold-1- (perfluoroalkyl) methylamine that has the structural formula II Cl A N C F 2 n *: (II) in which A and n are as described above, with a dienophile compound having the structural formula III (I I I) in which W and Y are as described above and Z is Cl, Br or I, and a base in the presence of a solvent. The present invention also presents novel N- (arylmethylene) -1-chloro-1- (perfluoroalkyl) methylamine compounds having the structural formula II (II) in which n and A are as described above, with the proviso thatwhen A is unsubstituted phenyl, p-chlorophenyl or p-methylphenyl, n is an integer different from 1. DETAILED DESCRIPTION OF THE INVENTION The process according to the present invention preferably consists of the reaction of a N- (aplmeth? len) -1-chloro-1- (? erfluoroalkyl) methylamine of the formula II with at least about one molar equivalent, preferably about one to four molar equivalents of a dienophile compound of the formula III and at least " a molar equivalent, preferably about one to four molar equivalents of a base in the presence of a solvent preferably in a temperature range of about 5 ° C to 100 ° C to form the compounds 2-ar-l-5- (perfluoroalkyl) ) Preparation of the formula I On the other hand, compounds of the formula I can be prepared by forming the dienophilic compounds of the paraffin III in situ This process consists in reacting a compound of N- (ar? lmet? len) -1 -cloro-1 - ( perfluoroalkyl) methylamine of formula II with preferably about one to four molar equivalents of an a.β-dihalo compound having the structural formula IV zyii HC-CK II wz (IV) in which W and Y are as described above and Z is Cl, Br or I, and at least about two molar equivalents, preferably about two to one molar equivalents of a base in the presence of a solvent, preferably in a temperature range of about ° C to 100 ° C to form the 2-aryl-5- (perfluoroalkyl) pyrrole compounds of the formula I.

Advantageously, the present invention presents new processes for the preparation of 2-ar? L-5- (perfluoroalkyl) pyrrole compounds that elude the use of Strecker synthesis. The compounds of the formula I according to the present invention can be isolated by conventional procedures such as dilution of the reaction mixture with water and filtration or, alternatively, extraction with a suitable solvent. Suitable extraction solvents include immiscible solvents in water such as ether, ethyl acetate, toluene, methylene chloride, and the like Suitable bases for use in the present invention include tp (alkyl Ci.C.sub.Hammas such as t-methylamine, triethylamine, t-propylamine, t-butylamine, diisopropylethylamine and the like, metal carbonates. alkaline such as potassium carbonate and sodium carbonate; alkali metal hydroxides such as potassium hydroxide and sodium hydroxide; alkali metal acetates such as potassium acetate and sodium acetate and heterocyclic tertiary amines including, but not limited to, 1, 8-diazab? Cycle [5 4 0] undec-7-epo (DBU). 1,5-d? Azab? C? Clo [4 3 0] nor --.- ene (DBN); 1,4-diazabicyclo [2.2.2] octane, substituted pipdine pipdines such as 2,6-d? Methylpipdine, 2-methylpipdine, 3-methylpipdine, 4-methylp? Pd? Pa and the like, quinoline and substituted quinolines. Preferred bases include tp- (alkyl C? .C4) amines. 1.8-diazabicyclo [5 4.0] undec-7-ene 1,5-d? Azabicyclo [4.3.0] non-5-ene. 1,4-diazabicyclo- [2.2.2] octane, potassium carbonate and sodium carbonate Solvents suitable for use in the present invention include, but are not limited to, carboxylic acid amides such as N, N-dimethylformamide. N, N-d? Met? Lacetam? Da and the like; N-substituted pyrrolidinones such as N-methylpyrrolidinopa and the like; nitriles such as acetonitrile, propionityl and the like, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and the like, ethers such as tetrahydrofuran, dioxane and the like, sulfoxides such as dimethyl sulfoxide and the like, as well as mixtures thereof. Preferred solvents they include the carboxylic acid amides and nitnets and mixtures thereof. N, N-dimethylformamide and acetonitide, as well as mixtures thereof, are especially suitable for use in the present invention. Examples of halogen according to the aforementioned are chlorine, bromine and iodine The terms "haloalkyl io C1-C4", "haloalkoxy C1.C4", "haloalkylthio C1.C4". "haloalkylsulfmyl C? .C4n, and" halsalkylsulfonyl C1.C4"are defined as C1 C4 alkyloxy C1.C4 alkoxy, C1-C4 alkylocyte, C1.C4 alkylsulfinyl or alkylsulphonyl C. substituted with one or more halogen atoms, respectively The present invention is especially useful for the preparation of compounds of the formula I in which W is hydrogen, Y is CN n is 1 or 2 L is hydrogen or halogen and each of M and Q is independently hydrogen, halogen, C1 C4 haloalkyl or C1.C4 haloalkoxy. In particular, the present invention is useful for the preparation of 2- (p-chlorophen? L) -5- (trifluoromethyl) pyrrol-3-carbonyl, 2- (3 5-d? chlorophen?) -5- (tpfluoromet? l) pyrrol-3-carbon? tr? lo, 2 - (3 4-d? Chlorophen? L) -5- (tpfluoromet? L) pyrrol-3-carbon? Tplo and 2- [4-) tr? Fluoromet? L) phen? L] -5- (tr ? fluoromet? l) pyrrol-3-carbonyl, etc. The present invention also relates to novel N- (arylmethylene) -1-chloro-1- (perfluoroalkyl) methylamine compounds having the structural formula II Cl N C F 2. n * l MI) in which n is an integer of 1, 2, 3, 4, 5, 6, 7 or 8; L is hydrogen or halogen; each of M and Q is independently hydrogen, halogen. CN, NO2, C1.C4 alkyl. haloalkyl C? C4: C1.C4 alkoxy: C1.C4 haloalkoxy, C1.C4 alkylthio; haloalkylthio C1.C4. alkylsulfinyl C1.C4. ' haloalkylsulfinyl C1.C4: C1-alkylsulfopyl. C. haloalkylsulfonyl d.C4. or, when M and Q are in adjacent positions, they can be taken together with the carbon atoms to which they are attached to form a ring in which MQ represents the structure -OCH20-. -OCF20- or -CH = CH-CH = CH-, R1, R2 and R3 are, independently, hydrogen, halogen, NO2, CHO or R2 and R3 can be taken together with the atoms to which they are attached to form a ring in which R2R3 is represented by the structure ; each of R4, R5, Re and R7 is independently hydrogen, halogen, CN or NO2 and X is O or S provided that, when A is unsubstituted phenyl, p-chlorophenyl or p-methylphenyl, n is an integer other than 1 The novel preferred compounds of formula II of the present invention are those in the which n is 1 or 2.

L is hydrogen or halogen and each of M and Q is independently hydrogen, halogen, haloalkyl C1.C4 or haloalkoxy. Cj Among the novel compounds of formula II of particular utility in the present invention include 1-Chloro-N- ( 3.5-d? Chlorobenzyl?) -2.2.2-: r? Fluoroet? Lam? Na. 1-Chloro-N- (3,4-a? Chlorobenzyl?) -2.2.2-tpfluoroethylamine, na and 1-chloro ^^^ -tr uoro-N- ^ -? Trifluoromethyl-benzylidin-ethylamine, among others.

The starting N- (arylmethylene) -1-chloro-1- (perfluoroalkyl) methylamine compounds of the formula II can be prepared, according to that illustrated in Diagram I, by the isomerization of a chloride compound of N- (arylmetyl) perfluoroalkyliformyl doyle of structural formula V with a tertiary amine, optionally at elevated temperature according to the methods described in Chemistry Letters, p. 1463-1464 (1983). DIAGRAM I ^ \ N 2 n - (V) Tertiary amine Suitable tertiary amines for use in the isomenzation of the compounds of formula V include tp- (C 1 -C 4) alkanes such as trimethylamine, tethylamine, tppropylamine, tpbutylamine, diisopropylethylamine and the like, and heterocyclic tertiary amines including although not limited to, 1 8-diazab [5 4 0] unaec-7-ene 1 5-d? azab? aclo [4 3 0] pon-5-ene.pipdin, substituted pyridines such as 2 6 -d? met? lp? r? dma 2-met? lp? pa? na. 3-met? lp? r? na na. 4-met? l? r? d? na and the like, qumolema and substituted qumoleins The amines I intended tertians include tn- (alk? C i C4) am? Nas. 1 8-day? Ab? C? Clo [5 4.0] unde-I-7-ene and 1,5-d? Azab? C? Clo [4 3 0] non-5-ene In a preferred embodiment of the present invention, the compound of formula V is isomepza with a tertiary amine in the presence of a solvent in a temperature range of about 15 ° C to 60 ° C. Suitable solvents for use in the preparation of the compounds of formula II include aromatic hydrocarbons such as toluene, benzene, xylenes and the like, as well as mixtures thereof. The N- (aryl-methyl) perfluoroalkylformimidoyl chloride compounds can be prepared according to the procedures described in U.S. Patent No. 5,195,986 and in Chemistry Letters, p. 1463-1464 * (1983) The initial dienophilic compounds of formula III are known in the art and can be prepared using conventional procedures. The compounds of the formulas III and "IV in which W is CmF2m +? Can be prepared according to the procedures described in U.S. Patent No. 5 068 390 The compounds of the formula I are useful for controlling insect pests and In addition, the compounds of the formula I can be used to prepare other insecticidal and monopolized arylpyrrole agents having the structural formula VI wherein R is C1.C4 alkyl. n is an integer of 1. 2, 3, 4, 5, 6. 7 or 8; L is hydrogen or halogen; each of M and Q is independently hydrogen, halogen, CN, NO;, C 1 -C haloalkyl, C 1 C 4 alkoxy, C 1 C 4 alkoxy; haloalkoxy C1.C4, alkylthio C1.C4. naloalkylthio C1.C4. C 1 -C 4 alkylsulfimyl; haloalkylsulfinyl C? .C4; alkylsulfonyl Ci. C. naioaloui.'sulíonilo C1.C4. or. when M and Q are in adjacent positions, they can be taken together with the carbon atoms to which they are attached to form a ring in which MQ represents the structure -OCH O-, -OCF2O- or -CH = CH-CH = CH- caaa one ae R;. R2 and R3 is. independently, hydrogen, halogen, NO. CHO or R; and R3 can be taken together with the atoms to which they are to form a ring in which R2R3 is represented by the structure - caaa one of R4 R5. Re and Rr is independently hydrogen, halogen, CN c NO; X is O or S Hal is a halogen atom and J is hydrogen or alkoxymethyl Ci.Ce The present invention is especially useful for the preparation of aplpyrole compounds of the formula VI in which Y is CN n is 2 or L is hydrogen or halogen and each of M and Q is independently hydrogen, halogen, haloalkyl Ct.C- or haloalkoxy C1.C4 Hal is Br or Cl and J is hiarogepo or ethoxyethyl Especially the present invention is useful for the preparation from Arylpyrrole compounds of the formula VI such as 4-bromo-2- (p-clsrofep? L) -1 - (etox? Met? L) -5- (tr? Fluoromethyl) p? Rrol-3-carPon? Tr? what do you mean) -Dromo-2- (3 4-d? ciorofen? l) -1 -. { etox? met? l) -5- (tr? fluorornet? l) pyrrol-3-ca-oonitrile and 4-promo-2- (pd? chlorophen? l) -5 ^ (tr? fluoromet? l) p Carboxymethylcarboxylate, etc. Advantageously, the aplipyrol compounds of Formula VI can be prepared by a process consisting of a) reacting a N-aplmethyl compound) -1-chloro-1 - (oen) iuoroalkine methylamine of formula II with a dienophile compound having the structural formula VII K C = C (VII) in which Y is as described above and Z is Cl, Br or I, and a base in the presence of a solvent to form a 2-aryl-5- (perfluoroalkyl) pyrrole compound having the structural formula VIII '(VII I) b) halogenating the compound of the formula VIII to form the arylpyrrole compound of the formula VI in which J is hydrogen and c) optionally, alkoxymethylating the compound of the formula VI in which J is hydrogen to form the arylpyrrole compound of the formula VI wherein J is alkoxymethyl Ci.Cß. On the other hand, the arylpyrrole compounds of the formula VI can be prepared by a process consisting of- a) the reaction of a compound N- (arylmethyl) -1-cioro-1- (perfluoroalkyl) methylamine of the formula II with a compound a, ß-dihalo that has the structural formula IX z and I! HC- CK I I K z (IX) wherein Y is as described above and Z is Cl, Br or I, and at least about two molar equivalents of a base in the presence of a solvent to form a 2-aryl-5- (perfluoroalkyl) compound? The formula that has the structural formula VIII r. (VI II) b) halogenated the compound of the formula VIII to form the aplpyrrole compound of the formula VI in which J is hydrogen and c) optionally, the alkoxymethyl penta compound of the formula VI in which J is hydrogen to form the aplpyrrole compound of the formula VI in which J is alkoxymethion C1.C5 The halogenated methods can be known methods such as the decpptos in U.S. Patent Nos. 5 010 098 and 5 449 789 Suitable ChCoxymethylation procedures for use in the present invention include conventional procedures known in the art (see for example U.S. Patent Nos. 5 010 098 and 5 359 090) In a preferred embodiment of the present invention, the alkoxymethylation process consists in reacting a compound of formula VI in which J is hydrogen with a compound d? - (alkoxy? Ci.C.-methane, N-N-dimethylformamide and phosphorus oxychloride in the presence of an aprotic solvent to form a reaction mixture and Treating the reaction mixture with a tertiary amine In order to facilitate a better understanding of this invention, the following examples are presented primarily for the purpose of illustrating the more specific details thereof. The scope of the present invention should not be considered to be limited. by these examples, but it covers the entire subject presented in the claims. PLO 1 Preparation of 1-chloro-N- (p-chlorobenzylidin) -2,2,2-trifluoroet? Sheet A solution of N- (p-chlorobenzyl) -2,2,2-tnfluoroacetimidoyl chloride (102.4 g 04 mol) in toluene is treated with triethylamipa (40.5 g, 0.4 mol) over the course of 45 minutes while the temperature rises to 40 ° C, it is stirred for 18 hours and filtered to remove the solids. The filtrate is concentrated in vacuo to remove toluene and the theylamine, and the resulting residue is distilled to VÓCÍO to give the title product as a colorless liquid (87.0 g 87% yield, mp 95-98 ° C). / 2.6 mmHg) Using the same procedure, although using the appropriately substituted acetylimidoyl chloride, the following compounds are obtained: M Q pf ° C / mmHg% yield Cl Cl 101 - 104 / 0.5 79 H CF 3 H Cl H Cl 1 10 - 1 12 / 0.9 84 EXAMPLE 2 Preparation of 2- (p-chlorophen? L) -5- (tr? FIuoromethyl) p? rrol-3-carbon? thlo A solution of 1 - (p-chlorobenzylidene) -2.2.2-t is treated by dripping. fiuoroetiiamma (9.0 g, 0.035 mol) and 2-chloroacrylonitrile (3.7 g, 0.42 mol) in N, Nc t? e!?! cr cr con with tetylamine (7.8 g, 0 077 mol) ) in a period of 45 minutes, when the temperature rises to 45 ° C, it is stirred at 55 - 5 ° C for 4 hours, stirred overnight at room temperature and diluted with water and ethyl acetate. Separate the organic layer, wash it with water and concentrate it. Acquired to obtain a residue The flash column chromatography of the residue using silica gel and a solution of ethyl acetate at 20% in nectane is obtained e. title product in the form of pale yellow solid (3.9 g. ^ '2% yield), which is identified by 1 H and 19 F NMR. Using the same procedure, although using the 1-chloro-2,2.2-: r, iiuoro-N- (benc? L? D? Pa? T? Tu? Da) et? Lam? Pa, duly replaced, the following compounds L M Q pf ° C H CF3 H 216 - 217.5 Cl H Cl EXAMPLE 3 Preparation of 2- (3,4-d? Chlorophen?) -5- (tpfluoromet? L) pyrrol-3-carbonyl chloride using 2-chloroacrylic? Tplo A solution of 1-chloro-N- (3 4-d? Chlorobenzyl? D? P) -2.2.2-trifluoroethylamine (11.6 g 0.04 mol) and 2-chloroacplon? Tlo (4, 2 g, 0.048 mol) in N, N-dimethylformamide with dusopropylethylamine (12.9 g 0.1 mol) over a period of 45 minutes during which the temperature rises to 40 ° C. stir at 55 ° C for 4 hours, stir overnight at room temperature and dilute with water and ethyl acetate. Separate the organic layer, wash with water and concentrate in vacuo to obtain a residue. Instant column chromatography. of the residue using silica gel and a = 20% ethyl acetate solution in heptane gives the title product as a white solid (5.8 g, 47.5% yield), which is identified by 1 H NMR and 15F EXAMPLE 4 Preparation of 2- (3 4-d? chlorophen? l) -5- (tr? fluoromethyl) pyrrole-3-carbonyl chloride using 2 3-d? chloroprop? on? tplo A solution of 1-chloro-N- (3,4-dichlorobenzylidin) -2,2,2-trifluoroethylamine (8.72 g, 0.03 mol) and 2,3-d? Chloropropronic acid (4) is treated by dripping. 3 g, 0.0345 mol) in NN-dimethylformamide with trielylamipa (11.1 g, 0.1 mol) over a period of 30 minutes during which the temperature rises to 55 ° C, is stirred at 55 ° C. C for 5 hours, cooled to room temperature and diluted with water and ethyl acetate. The organic layer is separated, washed with water and concentrated in vacuo to obtain a residue. The residue is dissolved in ethyl acetate and mixed with silica gel. The silica gel mixture is dried under vacuum and washed with a solution of 20% ethyl acetate in heptane. The resulting filtrate is concentrated to! The residue is triturated with heptane and a small amount of ethyl acetate to give the title product as a pale yellow solid (3.2 g, 35% yield) It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.

Claims

RFIVINDICATIONS Having described the invention as above, property is claimed as contained in the following:

1 A process for the preparation of a 2-aryl-5- (perfluoroalkyl) pyrrol compound having the structural formula I K (I) wherein W is hydrogen or CmFzm-u Y is CN, NO2 or CO2R R is C1.C4 alkyl each of m and n is independently an integer of 1, 2, 3, 4, 5, 6, 7 or 8, "' L is hydrogen or halogen each of M and Q is independently halogen hydrogen, CN, NO2, C1.C4 alkyl, C1.C4 haloalkyl, C1-C4 alkoxy, haloacycxy alkylthio d.C4; haloalkylthio C1.C4 alkylsulfinyl C1.C4. haloalkylsulfinyl C1.C4, alkylsulfonyl C1. C4 haloalkylsulfonyl or, when M and Q are in adjacent positions, they can be taken together with the carbon atoms to which they are attached to form a ring in which MQ represents the structure -OCH2O-, -OCF2O- or - CH = CH- CH = CH-; R ,. R2 and R3 are, independently, hydrogen, halogen, NO2, CHO or R2 and R3 can be taken together with the atoms to which they are attached to form a ring in which R2R3 is represented by the structure P < ^ 5 ^ 6 Pr i I '! - O C- C = C-; each of R4, R5. R5 and R7 is independently hydrogen, halogen, "CN or NC, and X is O or S the praesus is cararteriza ±) perqué ccnsiste in do r roenar a carpuestD - (arilmst? 1F?) C: -oi -íDerflL 3roa'qu? L) met? Lam? Na that has the structural formula II c: ^^ K C r. F 2 n. I I) in which A and n as described above, with a dienophile compound having structural formula III or an a.β-dihalo compound having the formula structure IV ; 1) (IV) where and Y are as described above and Z is Cl, Br or I, and a base in the presence of a solvent

2. The EUJO-HJ de ao-erdo with the reivinIicH -im l, catacte Lzadb prcx | i? the tese is. selected from the group consisting of a tri (alkyl dC ^ amine, an alkali metal carbonate, and a heterocyclic tertiary amine, 3 £ 1 μuraj of aauercb an the virriication l, IHIHI HTT- -D because the saLraate is « selected from the group consisting of a carboxylic acid amide and a nitrophoid and mixtures thereof 4 The PRCA according to the vip-tirpr? nl, prtrji? the diep? phyl is present in an amount of about one to four molar equivalents and the base is present in an amount of about one to four molar equivalents. 5 The praees of aa-erdb is the reivip-tirrr-irri 1, partj? the mpjesto -d.halo is present in an amount of about one to four molar eauivalenies and the base is present in an amount of about two to five molar equivalents ß The process according to claim 1, characterance ±> μx which is hiarogenic, and CN is n or 1 or 2. L is hydrogen or halogen and each of M and Q is independently hydrogen, halogen, haloalkyl C, C4 or haloalkoxy C, .C4 A process for the preparation of an arylpyrrole compound having the structural formula VI 'VI) in which F Y is CN. NO: or C02R. R is alkyl C, d. n is an integer of 1, 2. 3, 4. 5, 6, 7 or 8; L is hydrogen or halogen. each of M and Q is independently hydrogen, halogen, CN, NO2, C, C4 alkyl. C, .C4. C, C4 alkoxy. haioalkoxy C, .C4, alkylthio d.C4. haioalkylthio C, .C4. alkylsulfinyl C, .C4, haloalkylsulfipyl C, .C4; alkylsulfonyl C ,. C4 haioalkylsulfonyl C, .C4, or. when M and Q are in adjacent positions, they can be taken together with the carbon atoms to which they are attached, to form a ring in which MQ represents the structure -GCH2O-, -OCF2O- or -CH = CH-CH = CH-; each of R,, R2 and R3 is, independently, hydrogen, halogen, ño :. CHO or R: and R3 can be taken together with the atoms to which they are attached to form a ring in which R2R3 is represented by the structure each of R4, R5, R6 and R7 is independently hydrogen, halogen, CN or NO2; X is O or S; Hal is a halogen atom and J is hydrogen or alkoxymethyl d.C6. the pp ueao this character zadD pique irtr ^ e the siryrifptes steps: a) react a compound N- (aplmet? len) -1-chloro-1 - (perfluoroalkyl) met? lam? na of the formula II where A and n are as previously described with ur. diepofilo compound that has the formula EsLr * Jctur¿ Vil c with an a.β-dihalo compound that has the structural formula IX (VI D (IX! wherein Y is as described above and Z is Cl, Br or I, and a base in the presence of a solvent to form a 2-aryl-5- (perfluoroalkyl) compound having the formula structural VIII H (VI II) b) halogenating the compound of the formula VIII to form the compound arylpyrrole of the formula VI in which J is hydrogen and c) optionally, alkoxymethylating the compound of the formula VI in which J is hydrogen 8. The xBso ds aauerd- > s n the reiviptica ipp 7, face ha i / at > The step (c) consists in reacting the compound of the formula VI in which J is hydrogen with a di (C, C6) alkoxy methanoi NN-dimethylformamide compound and phosphorus oxychloride in the presence of an aprotic solvent to form a Mix the reaction and treat the reaction mixture with a tertiary amine. 9. A compound that structural formula II (I I) »K ** ^ P? • r ~? \ > p ~ m ¥ »n is an integer of 1, 2, 3, 4. 5, 6, 7 or 8; L is hydrogen or halogen; each of M and Q is independently hydrogen, halogen, CN, NO2, alkyl d.C4; haloalkyl d.C4; alkoxy d.d; haloalkoxy d.d, alkylthio C, _C4; haloalkylthio d.C4; alauylsulfinyl C, .C4, haloalkyl sulfinyl d.C4; alkylsulfonyl C, _ C4, haloalkylsulfonyl d.C4, or. when M and Q are in adjacent positions, they can be taken together with the carbon atoms to which they are attached to form a ring in which MQ represents the structure -OCH2O-, -OCF2O- or -CH = CH-CH = CH -; R,. R2 and R2 are, independently, hydrogen, halogen, NO2, CHO or R2 and R3 can be taken together with the atoms to which they are attached to form a ring in which R2R3 is represented by the structure - each of R4, R5. R6 and R7 is independently hydrogen, halogen, CN or NO2 and X is O or S provided that, when A is unsubstituted fepyl, p-chlorophenyl or p-methylphenyl, n is an integer other than 1. 0 The good-looking agreement with the rejvjbretkp im 9, «« rn-fr * ¡7rrh pprrj tn is 1 or 2; L is hydrogen or halogen and each of M and Q is independently hydrogen, halogen, haloalkyl C, .C4 or haloalkoxy d.C4. HEHJ € N OF THE INUBOEN A process is presented for the preparation of 2-aryl-5- (perfluoroalkyl) pyrrole compounds from N- (ar-methylene) -1-chloro-1 - (perfluoroalkyl) methylamino. The 2-aryl-5- (perfluoroalkyl, pyrrole compounds are useful for combating insect pests and mites, and can also be used to prepare other pesticidal arylpyrrole compounds.) In addition, the present invention has N- (aplmethylene) -compounds. 1-cycloalkyl- (perfluoroalkyl) methylamine which serve as an intermediary in the preparation of the aplpyrrole compounds