CA1160232A - Pyridyliminomethylbenzene derivatives - Google Patents

Abstract

ABSTRACT
A compound of general formula (II)

Description

3~
.

This invention relates to pyridyliminomethylbenzene derivatives and acid-addition salts thereof, and to their preparation. This is a divisional application for Canadian patent from Canadian Patent Application Serial No.
345,301 filed on February 8, 1980.
The invention provides a compound of general formula (II) xl - N = C /

)n ~ ~ ~ - ( )m (II~
N

or an acid addition salt thereof, ~herein Xl is halogen; m is 0, 1 or 2; Y is an alkyl, haloalkyl, alkoxy, halo-alkoxy, halo, nitro, aryloxy, haloaryloxy, cyano or alko~ycarbonyl moiety;
n is 0, 1 or 2; and Z is an alkyl, alkoxy or halo moiety.
The invention also provides a process for making a compound of formula (II) which comprises reacting a thionyl halide with an N-(3'-pyridyl)benzamide of general formula ~V):

\ N _ C ~

(Z~n ~ ~ (Y)m wherein m, n, Y and Z are defined as above.

The compo~mds of the invention are useful intermediates in the preparation of related pyridyliminomethylbenzene derivatives and acid-addition , ~

salts thereof, the latter derivatives being compounds of general formula:-N = C

~ ~ ~ )m ~I) wherein X is cyano, ethynyl, optionally-substituted alkyl, optionally substitu-ted alkoxy, cycloalkoxy, alkenyloxy, alkynyloxy, aryloxy, haloaryloxy, alkoxy-aryloxy, aralkyloxy, haloaralkyloxy, alkoxyaralkyloxy, optionally-substituted alkylthio> cycloalkylthio, alkenylthio, alkynylthio, arylthio, haloarylthio, alkoxyarylthio, aralkylthio, or a group of formula R
-N
\R2 where Rl and R2 are independently selected from hydrogen and optionally-sub-stitu~ed alkyl, or Rl and R2 together with the interjacent nitrogen atom form a heterocyclic ring of from 5 to 7 ring atoms, one of which ring atoms may be a further.heteroatom selected ~rom nitrogen, oxygen and sulphur; m is 0, 1 or 2;
Y is a hydrogen atom or an alkyl, haloalkyl, alkoxy, haloalkoxy, halo, nitro, aryloxy, haloaryloxy, cyano or alkoxycarbonyl moiety; n is 0, 1 or 2; Z is an alkyl, alkoxy or halo moiety; optional substituents being selected from halogen,alkoxy, aryloxy, alkylthio, arylthio, alkylamino, dialkylamino, alkalidenamino and aryl moieties. ~It is noted that when n=0 then Z is a hydrogen atom).
The compounds of formula I are novel compounds and are the subject matter of related Canadian Patent Application Serial No. 345,301. Such compoundshave been found to have fungicidal properties, and specific examples will be ~ii63Z32 given hereinafter to illustrate the excellent activity of compounds of formula I as fungicides and the versatility thereof in terms of the wide range of fungus species which can be controlled by using such compounds.
Accordingly, Canadian Patent Application 345,301 further provides a fungicidal composition comprising a compound of formula I as defined above ~or an acid-addition salt thereof) in association with at least one inert carrier therefor, and a method of making such a composition which comprises bringing a compound of formula I as defined above (or an acid-addition salt thereof) into association with at least one inert carrier therefor.
Further in accordance with the invention of Canadian Patent Application 345,301 there is provided a method of protecting a crop from fungal attack com-prising treating crops subject to or subjected to fungal attackl seeds of such crops or soil in which such crops are growing or are to be grown with a compound of formula I ~or an acid-addition salt thereof) or a composition according to that invention.
The defined pyridyliminomethylbenzene derivatives of formula I are, of course, compounds capable of forming acid-addition salts, for example, salts of hydrohalic acids, particularly of hydrochloric acid, or of sulphuric acid.
Such salts are, therefore, also novel compounds; and they are of interest as having the fungicidal activity of the pyridyliminomethylben~ene derivatives from which they are formed (in a manner well-known per se). It is also noted in regard to such compounds that desirably they should be non-phytotoxic, which can readily be determined by routine test, since normally this is a requirement of fungicidal compositions.
Referring to the compounds of formula I, the optional substituents in the optionally substituted alkyl, optionally-substituted alkoxy and optionally-substituted alkylthio groups are preferably selected from halogen, alkoxy, aryl--oxy, alkylthio, arylthio, alkylamino, dialkylamino, alkylidenamino and aryl moieties.
Alkyl, alkenyl, alkynyl, cycloalkyl, alkoxyaryl, and aralkyl moieties in the various substituents in formula I preferably contain up to 10 carbon atoms. Preferred aryl groups are phenyl groups. The alkyl, alkenyl and alkynyl groups may be straight-chain or branched groups.
Preferred halogen substituents are chlorine, fluorine and bromine atoms, chlorine being particularly preferred.
At present, preferred compounds of formula I from the point of view of utilising the fungicidal activity which has been found to arise from the presence of the 3'-pyridyliminomethylbenzene structure which characterises the compounds of formula I are the simpler ~overall molecular structure wise~ pyridylimino-methylbenzene derivatives in which n=0. However, there is also provided those additionally substituted pyridyliminomethylbenzene derivatives in which one or two of the defined substituents Z are present, which can be used, as desired, as fungicidally active compounds where, for example, particular characteristics, for example, particular physical properties are sought. The fungicidal activity achievable with the compounds of formula I, and particularly those in which n=0, is especially advantageous being such as to enable those in the art readily to formulate, on the basis of the result of standard biological and physical tests, a range of fungicidal compositions having the characteristics required for parti-cular end use applications, for example, either relatively broad or relatively specific activity fungus speciewise, activity which is transmitted through plant tissue ~i.e. is not confined to the surfaces tested), and, by simple variation of the nature of the defined substituents, compositions in which the active com-pound exhibits significant vapour pressure. Also, such compounds have the advan-tage of being usable in combination with other known fungicides where it is de-23~

sired to provide compositions exhibiting a particular spectrum and level of activity.
When X is a group of formula -NRlR , wherein R and R together with the interjacent carbon atom form aheterocyclic ring of from 5 to 7 ring atoms, the ring is advantageously a piperidinyl, pyrrolidinyl, piperazinyl, morpholinyl or thiamorpholinyl ring, a six-membered nitrogen-containing heterocyclic ring be-ing preferred.
Preferred compounds are those wherein X is alkyl, alkoxy, aryloxy, alkyloxyalkoxy, alkylthio, alkylamino, substituted alkylamino, for example, amino-alkyl amino and alkoxy-alkylamino, or dialkylamino, m is 0, 1 or 2, Y is halogen and n is 0. Advantageously X is alkoxy, aryloxy, alkylthio, mono-alkylamino, di-alkylamino or a six-membered nitrogen-containing heterocyclic ring attached to the carbon atom through its nitrogen atom; and preferably X is Cl 6 alkoxy, Cl 6 alkylthio or di~Cl 6 alkyl) amino. Advantageously (Y)m is a cyano, halo or haloalkyl substituent, and in the case of a single such substituent it is prefer-ably attached at the 4-position of the benzene ring. In such case a single halo substituent is preferred, and tY)m is then preferably a 4-chloro-substituent as, for example, in a preferred compound: 4-chloro-~3'-pyridyl) lmino-C-~isobutyl-thio~ methylbenzene.
However, compounds in which ~Y)m represents di-halo substitution are also particularly effective. In such case ~Y)m is preferably dichloro-, and advan~ageously the chlorine atoms are in the 2,4- or 3,4-positions of the benzene ring.
There are also provided processes for preparing the compounds of formula I. The compounds of formula I wherein X is other than optionally-substi-tuted alkyl are prepared by reac*ing a compound of the invention of general formula:

~L~L6~;~3Z

N = C /

~Z)n ~ ~ (Y)m ~II) where m, n, Y and Z are all as defined above and Xl is halogen, wlth a compound of formula Q - X

where X is as defined above other than alkyl and Q is hydrogen or an alkali metal atom, optionally in the presence of an acid acceptor. Xl is preferably a cnlorine atom.
The intermediates of formula II are themselves provided as one aspect of the invention. They are conveniently prepared by reacting a thionyl halide 1~ with the appropriate N-~3'-pyridyl) benzamide of general formula:

H O
\ N - C

~ m (V) where m, n, Y and Z are as defined above.
The compounds of formula I wherein X is optionally-substituted alkyl are prepared by reacting a 3-amino pyridine of general formula ~ )n ~ ~III) where n and Z are as defined above, with a compound of general formula 23Z:

X - C - ~ (IV) ~Y) where X is optionally-substituted alkyl.
Compounds of formula I in which X is optionally-substituted alkylthio, cycloalkylthio, alkenylthio, alkynylthio, arylthio, haloarylthio, alkoxyarylthio or aralkylthio can also be prepared by alkylation of the corresponding thio-anilides.
As previously stated the salts of the novel compounds of formula I can be prepared from such compounds by methods well-known per se. Accordingly, and with the specific exemplification of the formation of the hydrochlorides herein-after, it is considered unnecessary to describe such methods in detail since those in the art will be familiar with them.
A carrier in a composition bearing the active ingredient is any materi-al with which the active ingredient is formulated to facilitate application to the locus to be treated, which may for example be a plant, seed or soilj or to facilitate storage, transport or handling. A carrier may be a solid or a liquid, including a material which is normally gaseous but which has been compressed to form a liquid, and any of the carriers normally used in formulating fungicidal compositions may be used.

Suitable solid carriers include natural and synthetic clays and sili-cates, for example natural silicas such as diatomaceous earths; magnesium sili-cates, for example talcs; magnesium aluminium silicates, for example attapulgites and vermiculites; aluminium silicates, for example kaolinites, montmorillonites and micas; calcium carbonate; calcium sulphate; synthetic hydrated silicon oxides and synthetic calcium or aluminium silicates; elements, for example carbon and sulphur; natural and synthetic resins, for example coumarone resins, po]yvinyl ~6~;~32 chloride, and styrene polymers and copolymers; solid polychlorophenols; bitumen;
waxes, for example beeswax, paraffin wax, and chlorinated mineral waxes; and solid fertilisers, for example superphosphates.
Suitable liquid carriers include water; alcohols, for example isopro-panol and glycols; ketones, for example acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; ethers; aromatic or araliphatic hydrocarbons, for example benzene, toluene and xylene; petroleum fractions, for example kero-sine and light mineral oils; chlorinated hydrocarbons, for example carbon tetra-chloride, perchloroethylene and trichloroethane. Mixtures of different liquids are often suitable.
Fungicidal compositions are often formulated and transported in a con-centrated form which is subsequently diluted by the user before application.
The presence of small amounts of a carrier which is a surface-active agent facili-tates this process of dilution. Thus preferably at least one carrier in a com-position according to the invention is a surface-active agent. For example, a composition may contain at least two carriers, at least one of which is a surface-active agent.
A surface-active agent may be an emulsifying agent, a dispersing agent or a wetting agent; it may be nonionic or ionic. Examples of suitable surface-active agents include the sodium or calcium salts of polyacrylic acids and lignin sulphonic acids; the condensation products of fatty acids or aliphatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; fatty acid esters of glycerol, sorbitan, sucrose or pentaerythritol; condensates of these with ethylene oxide and/or propylene oxide;
condensation products of fatty alcohols or alkyl phenols, for example ~-octyl-phenol or p-octylcresol, with ethylene oxide and/or propylene oxide; sulphates or sulphates of these condensation products; alkali or alkaline earth metal salts, preferably sodium saltsJ of sulphuric or sulphonic acid esters containing at least 10 carbon atoms in the molecule, for example sodium lauryl sulphate, sodium secondary alkyl sulphatesJ sodium salts of sulphonated castor oil, and sodium alkylaryl sulphonates such as sodium dodecylbenzene sulphonate; and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide.
The compositions may for example be formulated as wettable powders, dusts, granules, solutions, emulsifiable concentrates, emulsions, suspension con-centrates and aerosols. Wettable powders usually contain 25, 50 and 75% w of active ingredient and usually contain, in addition to solid inert carrier, 3 - 10 % w of a dispersing agent and, where necessary, 0 - 10 % w of stabiliser(s) and/

or other additives such as penetrants or stickers. Dusts are usually formulated as a dust concentrate having similar composition to that of a wettable powder but without a dispersant, and are diluted in the field with further solid carrier to give a composition usually containing 1/2 - 10 % w of active ingredient.
Granules are usually prepared to have a size between 10 and 100 BS mesh (1.676 -0.152 mm), and may be manufactured by agglomeration or impregnation techniques.
Generally, granules will contain 1/2 - 25 % w active ingredient and 0 - 10 % of additives such as stabilisers, slow release modifiers and binding agents. Emulsi-fiable concentrates usually contain, in addition to a solvent and, when necessary, co-solvent, 10 - 50 % w/v active ingredient, 2 - 20 % w/v emulsifiers and 0 - 20 % w/v of other additives such as stabilisers, penetrants and corrosion inhibitors.
Suspension concentrates are usually compounded so as to obtain a stable non-sedimenting flowable product and usually contain 10 - 75 % w active ingredient~
0.5 - 15 % w of dispersing agents, 0.1 - 10 % w of suspending agents such as protective colloids and thixotropic ag0nts, 0 - lO % w of other additives such as deformers, corrosion inhibitors, stabilisers, penetrants and stickers, and water or an organic liquid in which the active ingredient is substantially in-23æ

soluble; certain organic solids or inorganic salts may be present dissolved inthe formulation to assist in preventing sedimentation or as antifree~e agents for water.
Aqueous dispersions and emulsions, for example compositions obtained by diluting a wettable powder or a concentrate according to the invention with water, also lie within the scope of the present invention. The said emulsions may be of the water-in-oil or of the oil-in-water type, and may have a thick 'mayonnaise' - like consistency.
In order to illustrate the fungicidal activity of the compounds the examples given hereinafter of a wide range of compounds within formula I and representative of the scope thereof include results obtained by subjecting these compounds to a variety of tests representative of the spectrum of fungus species against which fungicidal compositions are required for use. The following tests were carried out:

~Z3~

(a) Activity against a~ple ~owdery mildew (PODOSPMAERA LEUCOTRICHA;P.l) The test is a direct anti-sporulant one using a foliar spray. The upper surfaces of leaves of whole apple seedlings are inoculsted by spraying with an aqueous suspension containing 105 conidia/ml 2 days prior to treatment with the test compound. The inoculated plants are immediately dried and kept at glasshouse ambient temperatures and humidity prior to treatment. The plants are sprayed at a dosage of 1 kilogram o~ active material per hectare using a track sprayer. After drying the plants are returned to a compartment at ambient temperature and humidity for up to 9 days, followed by assessment. Assessment is based on the percentage of the lea~ area covered by sporulation compsred with that on leaves of control plants.
(b) Activity against vine dowr.y mildew (Plasmo~era viticola; Pv.t) The test is a translaminar protectsnt one using a foliar spray. The upper sur~aces of leaves of whcle vine plants are sprayed at a dosage of 1 kilogrsm of active material per hectare using a track sprayer. The lower surfaces of the leaves sre then inoculsted, up to 6 hours after treatment with the test compound, by spraying with an aqueous suspension containing 105 zoospro-&ngia/ml. The inoculated plants are kept ~or 24 hours in a high humidity compartment, 4 days at glasshouse ambient temperature and humidity and then returned for a further 24 hours to high humidity. Assessment is based on the percentage of the lea~ area covered by sporulation compsred with that on control leaves.
(c) Activity against vine grey mould (Botrytis cinerea;B.c) The test is a direct eradicant one using a foliar spray.
The under-surface of the detached vine leaves are inoculated by pipetting ten large drops of an aqueous suspension contsining 5 x 105 conidià/ml on to them. The inoculated leaves are kept uncovered o~ernight during which time the fungus has penetrated the leaf and a visible necrotic lesion may be apparent where the drop was ~ade. The in~ected regions are sprayed directly with a dosage of 1 Xg of active material per hectare using a track sprayer. When the spray has dried the leaves are covered with 23;2 -petri dish lids and the disease allowed to develop under the moist conditions. The extent of the necrotic lesion beyond the original drop together T~Tith the dosage of sporulation is compared with that on control lea~res.
(d) Activit~ a~ainst ~eanut leaf s~ot (Cercos~ora arachidicola;Ca) The test is a direct eradicant one using a ~oliar spray.
'~he upper surfaces of the leaves of peanut plants (12-20 cms high, in monopots) are inoculated by spraying with an aqueous suspension containing 105 conidia/ml 40-43 hours prior to treat~ent with the test compound. 'Lhe inoculated plarts are kept at high humidity and then allowed to dry d~ing the interval between inoculation and treatment by spraying at a dosase of 1 kg of active material per hectare using a track sprayer. After spraying the plants are moved to a humid compartment at 25-28 C for a further period of up to 10 da~s. Assessment is based on a comparison between the levels of disease on the treated and control plants.
(e) Activit~ against potato late blight (Phytophthora infestans~
'~he test measures the direct protectant activity of compounds applied as a foliar spray. Tomato plants, Cultivar Ailsa Craig, 1-15 cms high, in monopots are used. 'rhe whole plant is sprayed at a dosage of 1 kilogram of acti~re material per hectare using a track sprayer. The plant is then inoculated up to 6 hours a~ter treatment hTith the test compound, by spraying with an aqueous suspension containing 5 x 103 zoozporangia/ml. The inoculated plants are kept in hight humidity for 3 days. Assessment is bases on comparison between the levels of disease on the treated and control plants.
(f) Activit~ a~_irst barle~ owder~I mildew (~rysiphe ~raminis, E~.) '~he test measures the direct anti-sporulant activity of compounds applied as a foliar spray. For each compound about 40 barley seedlings were grown to the one-leaf stage in a plastic pot of sterile potting compost. Inoculation was effected by dusting the leaves ~ith conidia of Erysiphe graminis, spp. hordei.
24 ho~rs a~ter inoculation the seedlings were sprayed with a solution o~ the compound in a mixture of acetone (50~), surfactant .~;232 .

(0.04%) a~d water using a track sprayer. The rate of application was equivalent to 1 kg of active material per hectare. First assessment of disease was made 5 days after treatment, when the overall level of sporulation on the treated plants were compared with that on control plants.
The ext~nt of disease control achieved in such tests is expressed &S a control rating according to criteria in which a greater than 80% disease control is given the rating 2.
Specific examples of compounds in accordance uith the invention are provided by the following examples, which are provided as illustrative but in no way limitative examples.
Relevant data pertaining to each of these examples is given in the apperded Tables I and II. These tables include illustrative~
but non-limitative, rating 2 results (where available) in the range of tests described above. The nature and extent (test spread-wise) of the results quoted demonstrates the ~ood ar.d useful fungicidal activity attainable using compounds in accordance with the invention.
Example 1 - 4-Chloro-(3'-pyridyl)imino-C-(isoPropoxy)meth~lbenzene A stirred mixture of N-(3'-pyridyl)-4-chlorobenzamide (7 g, 0.03 mole) and thionyl chloride (22.5 ml) was heated under reflux for two hours. ~xcess thionyl chloride was then removed in vacuo and the residue, 4-chloro--(3'pyriayl)imino-C(chloro)-methylbenzene hydrochloride, was suspended in dry dimethoYyethane (75 ml). A
solution formed by dissolving sodium (2.43 g, 0.105 mole) in dry isopropanol (100 ml) was poured into the suspension and the resulting mixture was stirred for one hour at room temperature and then heated under re~lux for si~teen hours. The solvent component of the mixture was removed in vacuo, and the residue was treated with diethyl ether. The ethereal solution was washed twice with water and then aried over anhydrous magnesium sulphate.
A~ter removal of the ether, the residue was su~jected to chro-matography on a silica gel column, eluting with diethyl ether/
hexane (1:1). The title product was obtained as a colourless solid (yield, 53%) m.p. 65-67C. (Ref: WL ~o. 81910) ~ l16~;Z3~

A greater than 80~ disease control was achieved in the ?v.t test.
Exam~le 2 - 4-Chloro-(3'-Pyridyl)imino-C-(isoPro~ylthio)methylbenzene A stirred mixture ol N-(3l-pyridyl)-4-chlorooenzamide (7 g, 0.03 mole) and thionyl chloride (22.5 ml) was heated under reflux for two hours. Excess thionyl chloride was removed in vacuo, and the residue, 4-chloro-(3'-pyridyl)imino-C-(chloro)me~hylbenzene hydrochloride, was treated with dry pyridine (lO0 ml). Isopropyl mercapt&n (4.56 g, o.o6 mole) was added and the mixture was stirred and heated in an oil-bath at a temperature in the range from lO0-ll0C for sixteen hours. The solvent and other volatile components of the mixture were removed in vacuo, and the residue was treated with diethyl ether. The ethereal solution was washed three times with water and then dried over anhydrous magnesium su_phate. After removal of the ether, the residue ~as subjected to chromatography on a silica gel colu~n, eluting with diethyl ether!hexane (l:l). The ti-~le product was obtained as a yellow solid (yield, 70~) m.p. 55.5-57 C. (Re~ L No. 819633 A greater than 80% disease control was achieved in the E.g.
test.
E~amPle 3 - 4-Chloro-(3'-Pyridyl)imino-C-(di-n-butylamino)methylbenzene A stirred mixture of N-(3'-pyridyl)-4-ch~orobenzamide (7 g, .03 mole) and thionyl-chloride (22.5 ml) was heated under reflux for two hours. Excess thionyl chloride was removed in vacuo and the residue, 4-chloro-(3~-pyridyl)imino-c-tchloro)methylbenzene hydrochloride, was suspended in dry dimethoxyethane (125 ml).
Dry di-n-butylamine (19.4 g, 0.15 mole) T~as added and the resulting mixture was stirred at ambient temperature overnight. The solvent component of the mixture was removed in vacuo, and the residue was treated with diethyl ether. The ethereal solution was washed twice with water and then dried o~er anhydrous magnesium sulphate.
After removal of the ether, the residue was subjected to chromato-graphy on a silica gel column, eluting with diethyl e~her, and again on a silica gel column, eluting with diethyl ether/methylene dichloride (l:l). The title product was obtained as a viscous , ~

23%

oil (yield 28%). (Ref: WL No. 83216) A greater than ôO% was achieved in the E.g. test.
Analysis: c~lculated for N3ClC20H26 : C 69.9; H 7.6; N 12.2 found : C 69.9; H 8.1; N 12.0 Ex~m~le 4 - 4-chloro-t3'-~ridyl)iminomethylben~ene A stirred mixture of 3-aminop~yridine (9.4 g, 0.1 mole) and 4-chlorobenzaldehyde (14.05 g, 0.1 mole) in toulene (100 ml) was heated under reflux under a Dean and Star~ trap for two hours, a~ter which time the theoretical amount of water (1.8 ml) had collected. The reaction mixture was diluted with toluene (100 ml) and then dried over anhydrous magnesium sulphate. The solvent component of the mixture was removed in vacuo, 40/60 petroleum spirit was added to the residue, and the resulting solid material was filtered off, washed with 40/60 petroleum spirit, and dried.
The solid material was recrystallised from cyclohexane (150 ml) to give the title product (yield 75%) mp 80-82C. (Ref: WL ~o. 83421) Exam~les 5 to 37 The compounds listed in Tables I and II were prepared by similar methods to those described in Examples 1 to 4: -~Z3Z

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V?C> ;-- N N N N N ~ 0 5:
~ ~ o ~ o ~ o ~ 0 ~ O ~ C.)'J
~ O ~1 0 ~7 0 N O NO N O N O N O N O ~ O N O N O
¢ ~ ~; ~ z :4 ~; ~ z~ ~ ~ æ ~ æ ~ ; ~ z ~ æ ~ z _ . __ C~ ~I I
o . ~ r-l ~ 'r~ ~ 'r~ 'r~ O ~O t-- rl r~ .r~
~ 0 ,:J O O 0 0 a~ (~ o o o N NN N N N O
r~ V
~
C~l N N N N C"l _ _ _ ~ ~ N
X ~ J ~. ~ ~ ^r'~ ~ .
Z ~ ) N~ N~ ~(''1 ~N
5~ C , i ~ ) V ~N ~1 . ~ V I ~ V {~ C~
u~o o, o~ ol o 7 .
,~
O ,~ D ~ 0 ~ O r~
~ ~ ~ ~ ~ ~C~ ~ ~ ~ ~ ~ ~

O O O r-JO r~ r~( N ~ ~ r-l Z 0 ~o ~o Ir\ L'~ O O ~ N N
~ u~ ~ ~O~O ~ O ~ ~D ~O \~ ~
_ 0 0 CO0 0 0 CO 0 0 0 0 0

Claims (11)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:

1. A compound of general formula (II) (II) or an acid addition salt thereof, wherein X1 is halogen; m is 0, 1 or 2; Y is an alkyl, haloalkyl, alkoxy, halo-alkoxy, halo, nitro, aryloxy, haloaryloxy, cyano or alkoxycarbonyl moiety; n is 0, 1 or 2; and Z is an alkyl, alkoxy or halo moiety.

2. A compound according to claim 1, wherein Y is halogen; m is 0, 1 or 2;
and n is 0.

3. A compound according to claim 1, wherein (Y)m is a 4-halo substituent.

4. A compound according to claim 3, wherein (Y)m is a 4-chloro substitu-ent.

5. A compound according to claim 1, wherein Y is halogen; m is 1 or 2;
and n is 0.

6. A compound according to claim 5, wherein Y is chlorine.

7. A compound according to any one of claims 1, 2 or 5, wherein Y is chlorine, and m is 2, the substituent (Y)m being in the 2,4- or 3,4-position of the benzene ring.

8. A compound according to claim 1, 2 or 3, wherein X1 is chlorine.

9. A compound according to claim 4, 5 or 6, wherein X1 is chlorine.

10. A compound according to any one of claims 1, 2 or 5, wherein Y is chlorine, and m is 2, the substituent (Y)m being in the 2,4- or 3,4-position of the benzene ring; and X1 is chlorine.

11. A process for preparing a compound of formula II as defined in claim 1, which comprises reacting a thionyl halide with an N-(3'-pyridyl)benzamide of general formula (V):

wherein m, n, Y and Z are defined as in claim 1.