The invention provides a compound of general formula I wherein XisOorNH; Y is CH or N; W is methyl or methoxy; R1 and R6, which may be the same or different, are alkyi, alkenyl, alkynyl, carbocyclyl or heterocyclyl each of which may be substituted; R2 and R3, which may be the same or different, have the same meaning as R1, or R2 and R3 together with the atoms to which they are attached form an optionally substituted 5-to 7-membered heterocyclyl group; R4 is optionally substituted alkyl, (preferably unsubstituted alkyl having 1 to 5 carbon atoms); R5 is alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, halogen, cyano, nitro, alkoxy, alkylthio, haloalkoxy or optionally substituted phenyl; and q is 0 to 4 (preferably 0), wherein when q is 2,3 or 4, each R5 may be the same or different.

Any alkyl group present in the molecule may be straight or branched and is preferably of 1 to 10 carbon atoms, especially 1 to 7 and particularly 1 to 5 carbon atoms.

Any alkenyl or alkynyl group may be straight or branched and is preferably of 2 to 7 carbon atoms and may contain up to 3 double or triple bonds which may be conjugated, for example vinyl, allyl, butadienyl or propargyl.

Any reference to the term carbocyclyl or carbocyclic includes, saturated carbocyclyl groups, preferably cyclopropane, cyclopentane or cyclohexane; unsaturated carbocyclyl groups having up to three double bonds, which may or may not be conjugated; and aromatic carbocyclyl groups, preferably phenyl. Carbocyclyl groups are typically 3 to 8 membered rings. In addition, the term carbocyclyl includes any fused combination of the aforementioned carbocyclyl groups, for example napthalene, phenanthrene, indane and indene.

Any reference to the term heterocyclyl or heterocyclic includes both aromatic and non- aromatic heterocyclyl groups. Heterocyclyl groups are generally 5,6 or 7-membered rings containing up to 4 hetero atoms selected from nitrogen, oxygen and sulfur.

Examples of heterocyclyl groups are furyl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, imidazolyl, dioxolanyl, oxazolyl, thiazolyl, imidazolyl, imidazolinyl, imidazolidinyl, <BR> <BR> <BR> pyrazolyl, pyrazolinyl, pyrazolidinyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl,<BR> <BR> <BR> <BR> <BR> thiadiazolyl, pyranyl, pyridyl, piperidinyl, dioxanyl, morpholino, dithianyl, thiomorpholino, pyridazinyl, pyrimidinyl, pyrazinyl, piperazinyl, sulfolanyl, tetrazolyl, triazinyl, azepinyl, oxazepinyl, thiazepinyl, diazepinyl and thiazolinyl. In addition, the term heterocyclyl includes fused heterocyclyl groups, for example benzimidazolyl, benzoxazolyl, imidazopyridinyl, benzoxazinyl, benzothiazinyl, oxazolopyridinyl, benzofuranyl, quinolinyl, quinazolinyl, quinoxalinyl, dihydroquinazolinyl, benzothiazolyl, phthalimido, benzofuranyl, benzodiazepinyl, indolyl and isoindolyl.

Any alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl group, when substituted, may be substituted by at least one group, which may be the same or different, and may be selected from the group: nitro; halogen; cyano; acyl ;-O-acyl ;-S-acyl; optionally substituted carbocyclyl; optionally substituted heterocyclyl;-SFs; -Si (Ra) 3, where Ra is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl and optionally substituted heterocyclyl ;-ORb and-SRb where Rb is the same as Ra or hydrogen; NRCRd where Rc and Rd, which may be the same or different, are hydrogen,

optionally substituted alkyl, acyl, or Rc and Rd taken together with the nitrogen to which they are attached form a heterocyclyl group, preferably a 5 to 7-membered heterocyclyl group, which may be substituted and may contain other hetero atoms, for example morpholino, thiomorpholino or piperidinyl. Any carbocyclyl or heterocyclyl groups may also be substituted by optionally substituted alkyl, optionally substituted alkenyl and optionally substituted alkynyl. Particularly preferred substituents on any alkyl, alkenyl or alkynyl group are halogen, alkoxy, haloalkoxy, alkylthio or optionally substituted phenyl. Particularly preferred substituents on any carbocyclyl or heterocyclyl group are as defined above for alkyl, alkenyl or alkynyl, and also alkyl and haloalkyl.

The term acyl includes the residue of sulfur and phosphorus-containing acids as well as carboxylic acids. Examples of acyl groups are:-C (=O) Re,-C (=O) ORe, -C (=E) NReRf,-C (=O) N (Re) ORf,-C (=O) ONReRf,-C (=O) N (Re) NRfR9,-C (=O) SRe, -C (=S) SRe,-S (O) pRe,-S (O) 20Re,-S (O) pNReRf,-P (=E) (ORe) (ORf), and -C (=O)-C (=O) ORe; where p is 1 or 2; E is O, S or, where appropriate, NRe or NORe; and where Re, Rf and R9, which may be the same or different, are as defined for Rb hereinabove, or Re and Rf, or Rf and R9, together with the atom (s) to which they are attached may form a ring, preferably a 5 to 7-membered heterocyclyl group which may be substituted and may contain other hetero atoms.

Each crossed bond depicted in general formula I represents a double bond having either Z or E stereochemistry. It is intended that the invention includes individual isomers as well as mixtures thereof. The double bond attached to W preferably has E stereochemistry.

In cases where compounds of the invention exist as tautomeric isomers, the invention includes individual tautomers as well as mixtures thereof.

In cases where the compounds of the invention exist as optical isomers, the invention includes individual isomers as well as mixtures thereof.

Preferably R1 and R6, which may be the same or different, are alkyl or phenyl, each of which may be substituted. Any alkyl group may be substituted independently by

one or more alkenyl, alkynyl, cycloalkyl, halogen, cyano, nitro, alkoxy, alkylthio, haloalkoxy or optionally substituted phenyl groups (preferably halogen, haloalkyl or alkoxy). Any phenyl group may be substituted independently by one or more of the same groups defined for alkyl, or alkyl or haloalkyl (preferably alkyl, halogen, haloalkyl or alkoxy). It is particularly preferred that R6 is an unsubstituted alkyl group having 1 to 5 carbon atoms.

Preferably R2 and R3, which may be the same or different, are optionally substituted alkyl. When substituted, preferred substituents are-ORb, SRb, NRCRd, acyl, or an optionally substituted carbocyclic or heterocyclyl group. Particularly preferred substituents are benzoyl or phenyl, each of which may be substituted by one or more alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, halogen, nitro, cyano, alkoxy, alkylthio, haloalkoxy, or optionally substituted phenyl groups (especially alkyl, haloalkyl, halogen, alkoxy or phenyl).

It is especially preferred that R2 is unsubstituted alkyl and R3 is alkyl substituted by benzoyl or phenyl, each of which may be substituted by alkyl, haloalkyl, halogen or alkoxy or phenyl.

The compounds of the invention have activity as fungicides, especially against fungal diseases of plants, e. g. mildews and particularly barley powdery mildew (Erysiphe graminis) and vine downy mildew (Plasmopara viticola), rice blast (Pyricularia oryzae), cereal eyespot (Pseudocercosporella herpotrichoides), rice sheath blight (Pellicularia sasa/f//), grey mould (Botrytis cinerea), damping off (Rhizoctonia solamD, wheat brown rust (Puccinia recondita), late tomato or potato blight (Phytophthora infestans), apple scab (Venturia inaequalis), glume blotch (Leptosphaeria nodorum). Other fungi against which the compounds may be active include other powdery mildews, other rusts, and general pathogens of Deuteromycete, Ascomycete, Phycomycete and Basidomycete origin.

The compounds of the invention also have insecticidal, acaricidal and nematicidal activity and are particularly useful in combating a variety of economically important insects, acarids and plant nematodes, including animal ectoparasites and especially Diptera, such as sheep blow-fly, Lucilia sericata, and house-flies,

Musca domestica; Lepidoptera, including Plutella xylostella, Spodoptera littoralis, Heliothis armigera and Pieris brassicae; Homoptera, including aphids such as -Megoura viciae; Coleoptera, including corn rootworms (Diabrotica spp., e. g.

Diabrotica undecimpunctata); and spider mites, such as Tetranychus spp..

The invention thus also provides a method of combating pests (i. e. fungi, insects, nematodes and acarids) at a locus infested or liable to be infested therewith, which comprises applying to the locus a compound of formula 1.

The invention also provides an agricultural composition comprising a compound of formula I in admixture with an agriculturally acceptable diluent or carrier.

The composition of the invention may of course include more than one compound of the invention.

In addition the composition can comprise one or more additional active ingredients, for example compounds known to possess plant-growth regulant, herbicidal, fungicidal, insecticidal or acaricidal properties. Alternatively the compound of the invention can be used in sequence with the other active ingredient.

The diluent or carrier in the composition of the invention can be a solid or a liquid optionally in association with a surface-active agent, for example a dispersing agent, emulsifying agent or wetting agent. Suitable surface-active agents include anionic compounds such as a carboxylate, for example a metal carboxylate of a long chain fatty acid; an N-acylsarcosinate; mono-or di-esters of phosphoric acid with fatty alcohol ethoxylates or salts of such esters; fatty alcohol sulfates such as sodium dodecyl sulfate, sodium octadecyl sulfate or sodium cetyl sulfate; ethoxylated fatty alcohol sulfates; ethoxylated alkylphenol sulfates; lignin sulfonates; petroleum sulfonates; alkyl-aryl sulfonates such as alkyl-benzene sulfonates or lower alkyinaphthalene sulfonates, e. g. butyl-naphthalene sulfonate; salts of sulfonated naphthalene-formaldehyde condensates; salts of sulfonated phenol-formaldehyde condensates; or more complex sulfonates such as the amide sulfonates, e. g. the sulfonated condensation product of oleic acid and N-methyl taurine or the dialkyl sulfosuccinates, e. g. the sodium sulfonate of dioctyl succinate. Nonionic agents include condensation products of fatty acid esters,

fatty alcools, fatty acid amides or fatty-alkyl-or alkenyl-substituted phenols with ethylene oxide, fatty esters of polyhydric alcohol ethers, e. g. sorbitan fatty acid esters, condensation products of such esters with ethylene oxide, e. g. polyoxyethylene sorbitan fatty acid esters, block copolymers of ethylene oxide and propylene oxide, acetylenic glycols such as 2,4,7,9-tetramethyl-5-decyne-4, 7-diol, or ethoxylated acetylenic glycols.

Examples of a cationic surface-active agent include, for instance, an aliphatic mono-, di-, or polyamine as an acetate, naphthenate or oleate; an oxygen-containing amine such as an amine oxide or polyoxyethylene alkylamine; an amide-linked amine prepared by the condensation of a carboxylic acid with a di- or polyamine; or a quaternary ammonium salt.

The compositions of the invention can take any form known in the art for the formulation of agrochemicals, for example, a solution, a dispersion, an aqueous mulsion, a dusting powder, a seed dressing, a fumigant, a smoke, a dispersible powder, an emulsifiable concentrate or granules. Moreover it can be in a suitable form for direct application or as a concentrate or primary composition which requires dilution with a suitable quantity of water or other diluent before application.

An emulsifiable concentrate comprises a compound of the invention dissolved in a water-immiscible solvent which is formed into an mulsion with water in the presence of an emulsifying agent.

A dusting powder comprises a compound of the invention intimately mixed and ground with a solid pulverulent diluent, for example, kaolin.

A granular solid comprises a compound of the invention associated with similar diluents to those which may be employed in dusting powders, but the mixture is granulated by known methods. Alternatively it comprises the active ingredient absorbed or adsorbed on a pre-granular diluent, for example, Fuller's earth, attapulgite or limestone grit.

Wettable powders, granules or grains usually comprise the active ingredient in admixture with a suitable surfactant and an inert powder diluent such as china clay.

Another suitable concentrate is a flowable suspension concentrate which is formed by grinding the compound with water or other liquid, a wetting agent and a suspending agent.

The concentration of the active ingredient in the composition of the present invention, as applied to plants is preferably within the range of 0.0001 to 1.0 per cent by weight, especially 0.0001 to 0.01 per cent by weight. In a primary composition, the amount of active ingredient can vary widely and can be, for example, from 5 to 95 per cent by weight of the composition.

In the method of the invention the compound is generally applied to seeds, plants or their habitat. Thus, the compound can be applied directly to the soil before, at or after drilling so that the presence of active compound in the soil can control the growth of fungi which may attack seeds. When the soil is treated directly the active compound can be applied in any manner which allows it to be intimately mixed with the soil such as by spraying, by broadcasting a solid form of granules, or by applying the active ingredient at the same time as drilling by inserting it in the same drill as the seeds. A suitable application rate is within the range of from 5 to 1000 g per hectare, more preferably from 10 to 500 g per hectare.

Alternatively the active compound can be applied directly to the plant by, for example, spraying or dusting either at the time when the fungus has begun to appear on the plant or before the appearance of fungus as a protective measure.

In both such cases the preferred mode of application is by foliar spraying. It is generally important to obtain good control of fungi in the early stages of plant growth as this is the time when the plant can be most severely damaged. The spray or dust can conveniently contain a pre-or post-emergence herbicide if this is thought necessary. Sometimes, it is practicable to treat the roots of a plant before or during planting, for example, by dipping the roots in a suitable liquid or solid composition. When the active compound is applied directly to the plant a

suitable rate of application is from 0.025 to 5 kg per hectare, preferably from 0.05 to 1 kg per hectare.

In addition, the compounds of the invention can be applied to plants or parts thereof which have been genetically modified to exhibit a trait such as fungal and/or herbicidal resistance.

Compounds of the invention may be prepared, in known manner, in a variety of ways.

Compounds of general formula 1, i. e. compounds of formula la where X is oxygen, can be prepared from compounds of general formula 11 according to the following reaction scheme where Qa is a leaving group, preferably a halogen. Choice of base is governed by the nature of R3 and will be apparent to the skilled chemist. For example, when R3 is a benzylic group, a relatively weak base is preferred such as potassium carbonate in acetone solvent. Generally however the preferred base is a metal hydride, such as sodium hydride, in tetrahydrofuran solvent. (R5lq R6 SRZ (R5) Rg SR2 0 W, y 0 W, Y SR4 V<y O\R4 O O R R oo R4 O O (II) (la) Compounds of general formula 11 are themselves novel and accordingly the invention includes these compounds, where R1 and R2 are as defined above.

Compounds of formula 11 can be prepared by reacting compound of formula III with compound of formula IV. Preferred reaction conditions involve heating in methanol solvent. (R5)(R5lq R6 SR2 R 0, 0 H2NNHC (=S) SR2 (IV)/NNS Y N methanol/heat H R [) 0 R 0 0 (111) (11)

Compounds of formula III can be prepared by reacting compound of formula V and compound of formula VI with potassium carbonate in acetone according to the following reaction scheme, where Qb is a leaving group, preferably halogen. (R5) (R5) q 6 6 O K2C03/acetone/ HON reflux I O O W R Y \ 4 R Y \R4 00 0\ o (V) (Vl) (111)

Compounds of formula VI can be prepared using methods known to the skilled chemist, for example from the corresponding dicarbonyl compound by treatment with one equivalent of hydroxylamine hydrochloride.

Compounds of general formula V can be prepared by methods known in the art.

For instance, methods for preparing compounds of formula V, where W is methoxy, Y is CH, X is 0 and Qb is a halogen are given in EP 0 299 694; and where Y is N, X is 0 and Qb is a halogen, are given in EP 0 254 426.

Alternatively, compounds of general formula I can be prepared from other compounds of general formula 1. For instance, compounds of formula lb where X is NH can be prepared from compounds of formula la where X is 0, by treatment with NH2R4 amine, for example methylamine. (R5) 6 SR2 (R5) q 6 SR2 q \ 0\ N \ O\ /N N SR3 /N N SR3 r R1 NH2R4/solvent r H R1 zon tt Rft N 0 0 O O (la. (lb) Other methods will be apparent to the chemist skilled in the art as will be the methods for preparing starting materials and intermediates.

The following Examples also make apparent various methods of preparing compounds of the invention as well as starting materials and intermediates of the invention. Structures of isolated novel compounds were confirmed by elemental and/or other appropriate analyses.

Example 1 Methyl 3-methoxy-2-[({[(1-methyl-2-{[1-methylthio-1-(4-methylbenzyl thio)- methylidenelhydrazono} propylidene) amino] oxy} methyl) phenyllprop-2-enoate (Compound 42) A mixture of the product from stage b) (0. 6 g) and potassium carbonate (0.22 g) in acetone (20 ml) was heated under reflux for 30 minutes. The reaction mixture was allowed to cool to room temperature and 4-methylbenzyl chloride (0.14 ml) was added dropwise. The reaction mixture was then heated under reflux for a further 3 hours. The reaction mixture was allowed to cool to room temperature and filtered through kieselguhr. The filtrate and washings were concentrated and the resulting oil was purified by silica gel chromatography to give the title product as an oil.

Example 2 Methyl 3-methoxy-2-[({[(1-methyl-2-{[1-methylthio-1-([1-([3-trifluo romethyl]- benzol) ethyllthio) methylidenelhydrazonolpropylidene) aminol- oxy} methy)) pheny)] prop-2-enoate (Compound 50) A mixture of the product from stage b) (0.3 g) and sodium hydride (0.035 g) in tetrahydrofuran (20 ml) was stirred at room temperature for 30 mins. 2-Bromo-1- [3-(trifluoromethyl)phenyl]propanone (0.21 g) was added and the reaction mixture was stirred overnight at room temperature. Water (15 ml) was added and the mixture was extracted with ethyl acetate (3x50 ml). The combined organic extracts were dried (MgSO4) and concentrated to give the title compound as an oil.

Preparation of starting materials a) Methyl 3-methoxy-2-[({[(1-aceylethylidene)amino]oxy}methyl)phenyl]p rop- 2-enoate A mixture of methyl 3-methoxy-2-[2-(bromomethyl)phenyl]prop-2-enoate (EP 0 299 694) (6 g) 3-hydroximinobutan-2-one (2.13 g) and powdered potassium carbonate (2.9 g) in acetone (25 mis) was heated under reflux for 4 hours. The reaction mixture was allowed to cool and dilute hydrochloric acid added. The solution was extracted with ethyl acetate.

The combined organic extracts were washed with aqueous sodium hydrogen carbonate, dried (MgS04) and the solvent removed to give an oil which was purified by silica gel chromatography to give the title compound as an oil. b) Methy) 3-methoxy-2- [ (f [ (1-methy)-2-ffdithiocarboxvmethy)]- hydrazonolpropylidene) amino] oxymethyl) phenyl] prop-2-enoate A solution of the product from stage a) (4.14 g) and methyl hydrazinecarbodithioate (2.7 g) in methanol (50 ml) was stirred under reflux for 5 hours. The solution was cooled to room temperature and the resulting precipitate was filtered to give the title compound as a solid.

The following compounds (see Table 1) of formula Ic, i. e. compounds of general formula i where X is O, Y is CH, W is methoxy, R1, R2, R4 and R6 are methyl and q is 0, were prepared by methods analogous to those of Example 1 or 2.

Table 1 Compound R3 1 2-pyridylmethyl 2 cyclohexyimethyl 3 2-phenylethyl 4 4-CI-phenoxymethyl 5 2- (4-Ph-phenoxy) ethyl 6 2-(2-Me-phenoxy) ethyl 2-(4-MeO-phenoxy) ethyl 8 3-phenoxypropyl 93-(4-fluorophenoxy)propyl 10 3- (4-tert-butylphenoxy) propyl 113-(3,5-diCl-phenoxy)ethyl 12 benzoylmethyl 13 1-benzoylethyl 14 a-methylbenzyl 15 pivaloyloxymethyl 16 1-naphthylmethyl 17 methyl 18 butyl 19 pentyl 20 hexyl Compound R3 21 allyl 22 but-2-enyl 23 3-methylbut-2-enyl 24 3-methoxycarbonylprop-2-enyl 25 4-methylpent-3-enyl 26 6, 6-dimethylhept-2-en-4-ynyl 27propargyl 28 2-cyanoethyl 29 2-chlorobenzyl 30 2-methylbenzyl 31 2-cyanobenzyl 32 2-trifluoromethoxybenzyl 33 3-isopropoxybenzyl 34 4-chlorobenzyl 35 4-ethylsulfonylbenzyl 36 4-phenylbenzyl 374-(2-benzoxazolyl)benzyl 38 2, 4-diCl-benzyl 39 2, 6-diCi-benzyl 40 3, 5-diMeO-benzyl 41 2,3,4,5,6-pentafluorobenzyl 42 4-methylbenzyl 43 3-methylbenzyl 44 3, 4-dimethylbenzyl 45 3-CF3-benzyl 461-(4-Me-benzoyl)ethyl 47 1- (4-Br-benzoyl) ethyl 48 1- (4-F-benzoyl) ethyl 491-(4-Cl-benzoyl)ethyl 501-(3-CF3-benzoyl)ethyl 511-(2,4-diCl-benzoyl)ethyl

The above compounds were not solid at room temperature. 1 H N. M. R. data of these compounds are presented below.

Compound 1 (isomeric mixture) 1 H N. M. R. (CDC13) 8 (ppm) 2.08-2.18 (6H, m, 2 x CH3C=N), 2.50-2.56 (3H, m, SCH3), 3.70-3.82 (6H, m, 2 x OMe), 4.44- (2H, m, SCH2), 5.16 (2H, s, OCH2), 7.20-7.48 (6H, m, ArH), 7.62 (1H, s, =CHOMe), 7.65-8.58 (2H, m, Ar-H).

Compound 2 (isomeric mixture) 1H N. M. R. (CDCIg) 8 (ppm) 1.02 (2H, m, CH2), 1.26 (3H, m, CH2, CH2CHCH2), 1.72 (4H, m, 2xCH2), 1.90 (2H, m, CH2), 2.14-2.16 (6H, m, 2 x CH3C=N), 2.48-2.56 (3H, m, SCH3), 2.90-3.05 (2H, m, SCH2), 3.70-3.85 (6H, m, 2 x OCH3), 5.16 (2H, s, OCH2), 7.18-7.48 (4H, m, ArH), 7.60 (1H, s, =CHOMe).

Compound 3 (isomeric mixture) 1H N. M. R. (CDC) g) 5 (ppm) 2.15-2.24 (6H, m, 2 x CH3C=N), 2.50-2.60 (3H, m, SCH3), 3.08 (2H, m, CH2Ph), 3.28-3.40 (2H, m, SCH2), 3.70-3.85 (6H, m, 2 x OMe), 5.18 (2H, s, OCH2), 7.18-7.54 (9H, m, ArH), 7.62 (1H, s, =CHOMe).

Compound 4 (isomeric mixture) 1H N. M. R. (CDCI3) 6 (ppm) 1.98-2.10 (6H, m, 2 x CH3C=N), 2.18-2.54 (3H, m, SCH3), 3.64-3. 76 (6H, m, 2 x OMe), 5.08 (2H, s, OCH2), 5.48-5.76 (2H, s, SCH2O), 6.84-7.40 (8H, m, ArH), 7.54 (1H, s, =CHOMe).

Compound 5 (isomeric mixture) 1H N. M. R. (CDC13) 8 (ppm) 2.15-2.18 (6H, m, CH3C=N), 2.54-2.60 (3H, m, SCH3), 3.45-3.60 (2H, m, SCH2), 3.74-3.85 (6H, m, 2 x OMe), 4.35 (2H, m, CH2CH2O), 5.18 (2H, s, OCH2), 7.02-7.65 (14H, m, ArH and =CHOMe).

Compound 6 (isomeric mixture) 1H N. M. R. (CDCI3) o (ppm) 2.15-2.18 (6H, m, CH3C=N), 2.28 (3H, s, ArCH3), 2.50-2.60 (3H, m, SCH3), 3.45-3.60 (2H, m, SCH2), 3.74-3.85 (6H, m, 2 x OMe), 4.30 (2H, m, CH2CH2O), 5.18 (2H, s, OCH2), 6.88-7.50 (8H, m, ArH), 7.60 (1 H, s, =CHOMe).

Compound 7 (isomeric mixture) 1H N. M. R. (CDCI3) 8 (ppm) 2.12-2.18 (6H, m, 2xCH3C=N), 2.52-2.58 (3H, m, SCH3), 3.40-3.55 (2H, m, SCH2), 3.72-3.85 (9H, m, 3 x OMe), 4.25 (2H, m, CH2CH2O), 5.15 (2H, s, OCH2), 6.85-7.50 (8H, m, ArH), 7.62 (1H, s, = CHOMe).

Compound 8 (isomeric mixture) 1H N. M. R. (CDCI3) o (ppm) 2.16-2.20 (6H, m, 2xCH3C=N), 2.25 (2H, m, CH2CH2CH2), 2.50-2.56 (3H, m, SCH3), 3.25-3.35 (2H, m, SCH2), 3.74-3.82 (6H, m, 2 x OMe), 4.08 (2H, t, CH2OPh), 5.15 (2H, s, OCH2), 6.90-7.50 (9H, m, ArH), 7.60 (1 H, s, =CHOMe).

Compound 9 (isomeric mixture) 1H N. M. R. (CDC13) o (ppm) 2.15-2.20 (6H, m, 2xCH3C=N), 2.25 (2H, m, CH2CH2CH2), 2.50-2.58 (3H, m, SCH3), 3.22-3.36 (2H, m, SCH2), 3.70-3.85 (6H, m, 2 xOMe), 4.05 (2H, t, CH2CH2O), 5.15 (2H, s, OCH2), 6.85-7.50 (8H, m, ArH), 7.60 (1H, s, =CHOMe).

Compound 10 (isomeric mixture) 1 H N. M. R. (CDC13) o (ppm) 1.34 (9H, s, C (CH3) 3), 2.10-2.16 (6H, m, 2 x CH3C=N), 2.20 (2H, m, CH2CH2CH2), 2.50-2.58 (3H, s, SCH3), 3.25-3.35 (2H, m, SCH2), 3.70-3.85 (6H, m, 2 xOMe), 4.08 (2H, t, CH2CH2OPh), 5.18 (2H, s, OCH2), 6.88-7.50 (8H, m, ArH), 7.60 (1H, s, =CHOMe).

Compound 11 (isomeric mixture) 1 H N. M. R. (CDC13) 8 (ppm) 2.10-2.20 (6H, m, 2 x CH3C=N), 2.50-2.60 (3H, m, SCH3), 3.40-3.55 (2H, m, SCH2), 3.74-3. 84 (6H, m, 2 xOMe), 4.25 (2H, m, CH2CH2OPh), 5.15 (2H, s, OCH2), 6.85-7.50 (7H, m, ArH), 7.60 (1 H, s, =CHOMe).

Compound 1 2 (isomeric mixture) 1H N. M. R. (CDC13) 8 (ppm) 2.08-2.18 (6H, m, CH3C=N), 2.60 (2H, s, SCH2), 3.70-3.72 (3H, m, SMe), 3.80-3.84 (6H, m, 2 x OMe), 4.58-5.15 (2H, m, SCH2C = 0), 7.18-7.60 (8H, m, ArH), 8.05 (2H, m, ArH).

Compound 13 (isomeric mixture) 1H N. M. R. (CDC13) 8 (ppm) 1.60-1.70 (3H, m, CHCH3), 1.90-2.10 (6H, m, 2 x CH3C=N), 2.50-2.59 (3H, m, SCH3), 3.70-3.85 (6H, m, 2 x OMe), 5.15 (2H, s, OCH2), 5.65 (1H, q, CHCH3), 7.15-8.05 (10H, m, ArH and =CHOMe).

Compound 14 (isomeric mixture) 1H N. M. R. (CDC13) 8 (ppm) 1.750-2.04 (3H, m, CHCH3), 2.16 (6H, m, 2 x CH3C=N), 2.45-2.54 (3H, s, SCH3), 3.74-3.85 (6H, m, 2 x OMe), 4.85-5.10 (1H, m, CHCH3), 5.15 (2H, s, OCH2), 7.18-7.55 (9H, m, ArH), 7.62 (1H, s, =CHOMe).

Compound 1 5 (isomeric mixture) 1H N. M. R. (CDC13) # (ppm) 1.20-1.25 (9H, m, C (CH3) 3), 2.10-2.20 (6H, m, 2 x CH3C=N), 2.48-2.60 (3H, m, SCH3), 3.72-3.85 (6H, m, 2 x OMe), 5.15 (2H, s, OCH2), 5.50-5. 74 (2H, m, SCH2), 7.18-7.50 (4H, m, ArH), 7.62 (1H, s, =CHOMe).

Compound 1 6 (isomeric mixture) 1H N. M. R. (CDC13) 5 (ppm) 1.95-2.15 (6H, m, 2 x CH3C=N), 2.35-2.55 (3H, m, SCH3), 3.58-3.78 (6H, m, 2 x OMe), 4.66-4.84 (2H, m, SCH2), 5.05-5.10 (2H, m, OCH2), 7.10-8.05 (12H, m, ArH, C=CHOMe), Compound 17 (isomeric mixture) 1H N. M. R. (CDC13) 8 (ppm) 2.10-2.15 (6H, m, 2 x CH3C= N), 2.45 (3H, s, SCH3), 2.55 (3H, s, SCH3), 3.70-3.85 (6H, m, 2 x OMe), 5.15 (2H, s, OCH2), 7.15-7.50 (4H, m, ArH), 7.60 (1H, s, =CHOMe).

Compound 18 (isomeric mixture) 1H N. M. R. (CDC13) 8 (ppm) 0.95 (3H, t, CH2CH3), 1.48 (2H, m, CH2CH3), 1,75 (2H, m, SCH2CH2), 2.10-2.20 (6H, m, 2 x CH3C=N), 2.48-2.58 (3H, m, SCH3), 3.05-3.15 (2H, m, SCH2), 3.73-3.85 (6H, m, 2 x OMe), 5.15 (2H, s, OCH2), 7.18-7.50 (4H, m, ArH), 7.62 (1H, s, =CHOMe).

Compound 19 (isomeric mixture) 1H N. M. R. (CDC13) 5 (ppm) 0.92 (3H, t, CH2CH3), 1.38 (4H, m, CH2CH2CH3), 1.75 (2H, m, SCH2CH2), 2.10-2.20 (6H, m, 2 x CH3C=N), 2.50-2.58 (3H, s, SCH3), 3.05-3.15 (2H, m, SCH2), 3.72-3.85 (6H, m, 2 x OMe), 5.15 (2H, s, OCH2), 7.18-7.50 (4H, m, ArH), 7.62 (1H, s, =CHOMe).

Compound 20 (isomeric mixture) 1H N. M. R. (CDC13) 8 (ppm) 0.90 (3H, t, CH2CH3), 1.35 (4H, m, 2 x CH2), 1.45 (2H, m, CH2), 1.74 (2H, m, SCH2CH2), 2.10-2.20 (6H, m, 2 x CH3C=N), 2.48- 2.58 (3H, m, SCH3), 3.05-3.15 (2H, m, SCH2), 3.70-3.85 (6H, m, 2 x OMe), 5.18 (2H, s, OCH2), 7.18-7.50 (4H, m, ArH), 7.62 (1H, s, =CHOMe).

Compound 21 (isomeric mixture) 1 H N. M. R. (CDC13) 5 (ppm) 2.10-2.20 (6H, m, 2 x CH3C = N), 2.50-2.58 (3H, m, SCH3), 3.72-3.85 (7H, m, 2 x OMe and SCH2), 5.17 (2H, s, OCH2), 5.20 (1H, m, =CH), 5.35 (1H, d, =CH), 5.95 (1H, m, SCH2CH=), 7-18-7.50 (4H, m, ArH), 7.62 (1H, s, =CHOMe).

Compound 22 (isomeric mixture) 1 H N. M. R. (CDCi3) o (ppm) 1.70 (3H, d, CHCH3), 2.10-2.20 (6H, m, 2 x CH3C = N), 2.50-2.55 (3H, m, SCH3), 3.65-3.78 (8H, m, 2 x OMe and SCH2), 5.15 (2H, s, OCH2), 5.50-5.85 (2H, m, CH=CH), 7.18-7.50 (4H, m, ArH), 7.62 (1 H, s, =CHOMe).

Compound 23 (isomeric mixture) 1H N. M. R. (CDC13) 8 (ppm) 1.70-1.80 (6H, m, C=CMe2), 2.10-2.20 (6H, m, 2 x CH3C = N), 2.48-2.58 (3H, m, SCH3), 3.68-3.85 (8H, m, 2 x OMe and SCH2), 5.15 (2H, s, OCH2), 5,30-5.38 (1H, m, CH = C), 7.18-7.50 (4H, m, ArH), 7.62 (1H, s, =CHOMe).

Compound 24 (isomeric mixture) 1H N. M. R. (CDCI3) ô (ppm) 2.10-2.20 (6H, m, 2 x CH3C=N), 2.50-2.58 (3H, m, SCH3), 3.50-3.95 (11 H, m, 2 x OMe, SCH2 and CO2Me), 5.15 (2H, s, OCH2), 6.00-6.10 (1H, m, =CHC02Me), 7.04 (1H, m, CH=CHC02Me), 7.18-7.50 (4H, m, ArH), 7.62 (1H, s, =CHOMe).

Compound 25 (isomeric mixture) 1H N. M. R. (CDCl3) 8 (ppm) 1.68-1.78 (6H, br m, 2 x =CMe), 2.10-2.20 (6H, m, 2 x CH3C=N), 2.44 (2H, m, CH2C=), 2.50-2.58 (3H, m, SCH3), 3.00-3.15 (2H, m, SCH2), 3.72-3.84 (H, m, 2 x OMe), 5.18 (2H, br s, OCH2), 7.18-7.50 (4H, m, ArH), 7.62 (1 H, s, =CHOMe).

Compound 26 (isomeric mixture) 1 H N. M. R. (CDCl3) 8 (ppm) 1.25-1.35 (9H, m, C (CH3) 3), 2.10-2.20 (6H, m, 2 x CH3C=N), 2.50-2.58 (3H, m, SCH3), 3.70-3.75 (8H, m, 2 x OMe and SCH2), 5.18 (2H, bs, OCH2), 5.60-5.74 (1H, m, C=CHC=C), 6.00-6.20 (1H, m, CH2CH), 7.18-7.50 (1 H, m, ArH), 7.62 (1H, s, =CHOMe).

Compound 27 (isomeric mixture) 1H N. M. R. (CDCl3) 8 (ppm) 2.07 and 2.35 (1H, 2 x t, C-CH), 2.13-2.20- (6H, m, 2 x CH3C=N), 2.50-2.60 (3H, s, SCH3), 3.70-3.95 (8H, m, 2 x OMe and SCH2), 5.18 (2H, bs, CH2O), 7.18-7.50 (4H, m, ArH), 7.62 (1H, s, =CHOMe).

Compound 28 (isomeric mixture) 1H H N. M. R. (CDCI3) o (ppm) 2.10-2.20 (6H, m, 2 x CH3C =N), 2.50 (3H, bs, SCH3), 2.85-2.92 (2H, m, CH2CN), 3.30-3.38 (2H, m, SCH2), 3.70-3.85 (6H, m, 2 x OMe), 5.18 (2H, bs, OCH2), 7.18-7.50 (4H, m, ArH), 7.62 (1 H, s, =CHOMe).

Compound 29 (isomeric mixture) 1 N. M. R. (CDC13) o (ppm) 2.10-2.18 (6H, m, 2 x CH3C=N), 2.50-2.60 (3H, m, SCH3), 3.72-3.86 (6H, m, 2 x OMe), 4.42-4.57 (2H, m, SCH2), 5.16-5.18 (2H, m, OCH2), 7.13-7.57 (8H, m, ArH), 7.60-7.62 (1H, m, =CHOMe).

Compound 30 (isomeric mixture) 1 H N. M. R. (CDCl3) # (ppm) 2.10-2.22 (6H, m, 2 x CH3C=N), 2.45-2.64 (6H, m, ArCH3 and SCH3), 3.72-3.85 (6H, m, 2 x OMe), 4.30-4.46 (2H, m, SCH2), 5.15- 5.18 (2H, m, OCH2), 7.15-50 (8H, m, ArH), 7.60-7.64 (1H, m, =CHOMe).

Compound 31 (isomeric mixture) 1H N. M. R. (CDCl3) # (ppm) 2.10-2.20 (6H, m, 2 x CH3C = N), 2.50-2.58 (3H, m, SCH3), 3.70-3.85 (6H, m, 2 x OMe), 4.50-4.62 (2H, m, SCH2), 5.18 (2H, bs, OCH2), 7.18-7.70 (9H, m, 8 x ArH and =CHOMe).

Compound 32 (isomeric mixture) 1H N. M. R. (CDC13) 8 (ppm) 2.10-2.20 (6H, m, 2 x CH3C=N), 2.50-2.60 (3H, m, SCH3), 3.72-3.84 (6H, m, 2 x OMe), 4.35-4.50 (2H, m, SCH2), 5.18 (2H, bs, OCH2), 7.18-7.58 (8H, m, ArH), 7.62 (1H, s, =CHOMe).

Compound 33 (isomeric mixture) 1 H N. M. R. (CDC13) 8 (ppm) 1.25-1.40 (6H, m, CH (CH3) 2), 2.05-2.25 (6H, m, 2 x CH3C=N), 2.50-2.58 (3H, m, SCH3), 3.68-3.84 (6H, m, 2 x OMe), 4.15 and 4.56 (1H, m, CH (CH3) 2), 4.25-4.40 (2H, m, SCH2), 5. 15 (2H, s, OCH2), 6.80- 7.50 (8H, m, ArH), 7.60 (1H, bs, =CHOMe).

Compound 34 (isomeric mixture) 1 N. M. R. (CDC13) 8 (ppm) 2.10-2.20 (6H, m, 2 x CH3C=N), 2.50-2.58 (3H, m, SCH3), 3.70-3.86 (6H, m, 2 x OMe), 4.25-4.38 (2H, m, SCH2), 5.18 (2H, bs, OCH2), 7.18-7.50 (8H, m, ArH), 7.60-7.62 (1H, m, =CHOMe).

Compound 35 (isomeric mixture) 1 H N. M. R. (CDC13) 8 (ppm) 1.58 (3H, t, SO2CH2CH3), 2.10-2.20 (6H, m, 2 x CH3C=N), 2.50-2.58 (3H, m, SCH3), 3.30 (2H, m, SO2CH2), 3.70-3.88 (6H, m, 2 x OMe), 4.25-4.40 (2H, m, SCH2), 5.15 (2H, bs, OCH2), (8H, m, ArH), 7.60 (1H, bs, =CHOMe).

Compound 36 (isomeric mixture) 1 H N. M. R. (CDC13) o (ppm) 2.10-2.25 (6H, m, 2 x CH3C=N), 2.50-2.60 (3H, m, SCH3), 3.70-3.71 (6H, m, 2 x OMe), 4.35-4.50 (2H, m, SCH2), 5.15-5.16 (2H, m, OCH2), 7.18-7.70 (14H, m, ArH and =CHOMe).

Compound 37 (isomeric mixture) 1 H N. M. R. (CDCI3) o (ppm) 2.10-2.20 (6H, m, 2 x CH3C=N), 2.50-2.60 (3H, m, SCH3), 3.70-3.85 (6H, m, 2 x OMe), 4.35-4.50 (2H, m, SCH2), 5.18 (2H, m, OCH2), 7.18 (1H, m, ArH), 7.30-7.70 (8H, m, 7 x ArH and =CHOMe), 7.78 (1H, m, ArH) and 8.24 (3H, m, ArH).

Compound 38 (isomeric mixture) 1H N. M. R. (CDCl3) # (ppm) 2.10-2.20 (6H, m, 2 x CH3C=N), 2.50-2.60 (3H, m, SCH3), 3.70-3.85 (6H, m, 2 x OMe), 4.35-4.50 (2H, m, SCH2), 5.18 (2H, m, OCH2), 7. 15-7. 58 (7H, m, ArH), 7.60-7.61 (1 H, m, = CHOMe).

Compound 39 (isomeric mixture) 1H N. M. R. (CDC13) 5 (ppm) 2.18-2.28 (6H, m, 2 x CH3C=N), 2.48-2.65 (3H, m, SCH3), 3.70-3.87 (6H, m, 2 x OMe), 4.64-4.79 (2H, m, SCH2), 5.15-5.19 (2H, m, OCH2), 7.19-7.50 (7H, m, ArH), 7.60-7.63 (1H, m, =CHOMe).

Compound 40 (isomeric mixture) 1 H N. M. R. (CDC13) 5 (ppm) 2.05-2.10 (6H, m, 2 x CH3C=N), 2.40-2.50 (3H, m, SCH3), 3.62-3.63 (3H, m, OMe), 3.70-3.78 (9H, m, 3xOMe), 4.15-4.28 (2H, m, SCH2), 5.08-5.10 (2H, m, OCH2), 6.30-7.40 (7H, m, ArH), 7.55 (1 H, m, =CHOMe).

Compound 41 (isomeric mixture) 1 H N. M. R. (CDC13) o (ppm) (6H, m, 2 x CH3C=N), 2.48-2.63 (3H, m, SCH3), 3.70-3.87 (6H, m, 2 x OMe), 4.35-4.50 (2H, m, SCH2), 5.18-5.19 (2H, m, OCH2), 7.18-7.48 (4H, m, ArH), 7.60-7.62 (1H, m, =CHOMe).

Compound 42 (isomeric mixture) 1 N. M. R. (CDC13) 5 (ppm) 2.10-2.18 (6H, m, 2 x CH3C=N), 2.32 (3H, m, ArMe), 2.44-2.56 (3H, m, SMe), 3.68-3.80 (6H, m, 2 x OMe), 4.20-4.36 (2H, m, SCH2), 5.12 (2H, m, OCH2), 7.1-7.45 (8H, m, ArH), 7.58 (1H, m, =CHOMe).

Compound 43 (isomeric mixture) 1H H N. M. R. (CDCl3) 5 (ppm) 2.08-2.15 (6H, m, 2 x CH3C = N), 2.35 (3H,-s, ArMe), 2.45-2.58 (3H, m, SMe), 3.68-3.80 (6H, m, 2 x OMe), 4.24-4.38 (2H, s, SCH2), 5.13 (2H, m, OCH2), 7.05-7.45 (8H, m, ArH), 7.58 (1H, m, =CHOMe).

Compound 44 (isomeric mixture) 1H N. M. R. (CDCI3) ô (ppm) 2.05-2.15 (6H, m, 2 x CH3C=N), 2.25 (6H, s, 2 x ArMe), 2.44-2.58 (3H, m, SMe), 3.65 (6H, m, 2 x OMe), 4.20-4.36 (2H, m, SCH2), 5.12 (2H, m, OCH2), 7.05-7.45 (7H, m, ArH), 7.58 (1H, m, =CHOMe).

Compound 45 (isomeric mixture) 1H N. M. R. (CDC13) 5 (ppm) 2.04-2.10 (6H, m, 2 x CH3=N), 2.40-2.50 (3H, m, SMe), 3.60-3.74 (6H, m, 2 x OMe), 4.22-4.38 (2H, m, SCH2), 5.06 (2H, s, OCH2), 7.10-7.60 (8H, m, ArH), 7.65 (1H, m, =CHOMe).

Compound 46 (isomeric mixture) 1H N. M. R. (CDCl3) 5 (ppm) 1.64 (3H, d, CHMe), 1.92-2.12 (6H, m, 2 x CH3C=N), 2.42 (3H, s, ArMe), 2.48-2.55 (3H, m, SMe), 3.68-3.80 (6H, m, 2 x OMe), 5.12 (2H, m, OCH2), 5.62 (1H, q, CHMe), 7.15-7.45 (6H, m, ArH), 7.57 (1H, m, =CHOMe), 7.93 (2H, d, ArH).

Compound 47 (isomeric mixture) 1H N. M. R. (CDCl3) 8 (ppm) 1.62 (3H, d, CHMe), 2.14 (6H, m, 2 x CH3C=N), 2.48 (3H, s, SMe), 3.68-3.80 (6H, m, 2 x OMe), 5.12 (2H, m, OCH2), 5.54 (1H,

q, CHMe), (4H, m, ArH), 7.58 (1H, s, =CHOMe), 7.60 (2H, d, ArH), 7.88 (2H, d, ArH).

Compound 48 (isomeric mixture) 1 H N. M. R. (CDC13) 5 (ppm) 1.64 (3H, d, CHMe), 2.10-2.15 (6H, m, 2 x CH3C=N), 2.22-2.25 (3H, m, SMe), 3.68-3.80 (6H, m, 2 x OMe), 5.10 (2H, m, OCH2), 5.56 (1H, q, CHMe), 7.10-7.58 (8H, m, 7 x ArH and =CHOMe) and 8.05 (1 H, m, ArH).

Compound 49 (isomeric mixture) 1H N. M. R. (CDCI3) o (ppm) 1.62 (3H, d, CHMe), 2.10-2.15 (6H, m, 2xCH3C=N), 2.48 (3H, m, SMe), 3.68 (3H, m, OMe), 3.82 (3H, m, OMe), 5.10 (2H, m, <BR> <BR> <BR> <BR> OCH2), 5.55 (1H, q, CHMe), 7.15 (1H, m, ArH), 7.30 (2H, m, ArH), 7.45 (3H, m, ArH), 7.58 (1H, m, =CHOMe) and 7.98 (2H, m, ArH).

Compound 50 (isomeric mixture) 1H N. M. R. (CDC13) 8 (ppm) 1.65 (3H, d, CHMe), 2.05-2.10 (6H, m, 2 x CH3C=N), 2.48 (3H, m, SMe), 3.66-3.80 (6H, m, 2 x OMe), 5.12 (2H, m, OCH2), 5.60 (1H, q, CHMe), 7.16-7.44 (4H, m, ArH), 7.57 (1H, m, =CHOMe), 7.60-8.26 (4H, s, ArH).

Compound 51 (isomeric mixture) 1H N. M. R. (CDC13) 5 (ppm) 1.65 (3H, d, CHMe), 2.05-2.10 (6H, m, 2 x CH3C = N), 2.42 (3H, s, SMe), 3.68-3.82 (6H, m, 2 x OMe), 5.15 (2H, m, OCH2), 5.32 (1H, q, CHMe), 7.15-7.53 (7H, m, ArH) and 7.60 (1H, s, =CHOMe) The following compounds (see Table 2) of formula Id, i. e. compounds of general formula I where X is 0, Y is N, W is methoxy, R2 and R6 are methyl and q is 0, were prepared by methods analogous to those of Example 1 or 2, wherein methyl 3-methoxy-2-[2-(bromomethyl) phenyl] prop-2-enoate[2-(bromomethyl) phenyl] prop-2-enoate was replaced by methyl 2-(methylimino)-2-[2-(bromomethyl) phenyllethanoate(methylimino)-2-[2-(bromomethyl) phenyllethanoate (for preparation see EP 0 254 426).

Table 2 Compound R4m.p./°CR3 1-(4-Br-benzoyl)ethylMeoil101Me 102 Me 1- (4-F-benzoyl) ethyl Me oil 103 Me 1- (3-CF3-benzoyl) ethyl Me oil 104 Me 1- (4-Me-benzoyl) ethyl Me oil 105 Me 1- (2, 4-diMe-benzoyl) ethyl Me oil 106 Me allyl Me oil 107 Me 3-methylbenzyl Me oil 3-CF3-benzylMeoil108Me 109 Me 3, 4-dimethylbenzyl Me oil 110 Me propargyl Me oil 111 Me 1- (3, 5-diF-benzoyl) ethyl Et oil 1-(4-MeO-benzoyl)ethylEtoil112Me 113 Me 1- (3-CI-benzoyl) ethyl Et oil 114 Me 1- (2, 4-diCl-benzoyl) ethyl Et oil 1-(4-CF3-benzoyl)ethylEtoil115Me 1-(2,6-diF-benzoyl)ethylEtoil116Me 117 Me 1- (3, 4-methylenedioxybenzoyl) ethyl Et oil 1-(2-CF3-benzoyl)ethylEtoil118Me 1-[(4,-benzyloxy)benzoyl]ethylEtoil119Me 1-(3,4-diCl-benzoyl)ethylEtoil120Me 1-benzoylethylEtoil121Me 1-(2,5-diF-benzoyl)ethylEtoil122Me Compound R4m.p./°CR3 123 Me 4-CI-phenacyl Me 114-5 124 Me 3, 4-diCi-phenacyl Me 102-5 125 Me 4-CN-phenacyl Me 121-3 126 Me 2-naphthoylmethyi Me 122-3 127 Me phenacyl Me 96-8 128 Me 1-oxo-2-indanyl Et 108-10 129 Me 1-benzoyl-1-methylethyl Et oil 130 Me a-benzoylbenzyl Et 64-7 131 Me 1- (4-CI-benzoyl) propyl Et oil 132 Me 1-benzoylpropyl Et oii 133 Ph 4-phenylbenzyl Me oil 134 Ph 1- (4-CI-benzoyl) ethyl Me oil 135 Ph methyl Me oil 136 Ph ethyl Me oil

The 1 H N. M. R. data of those compounds in Table 2 which were not solid at room temperature are presented below.

Compound 101 1 H N. M. R. (CDC13) o (ppm) 1.55-1.65 (3H, m, CHMe), 1.85 (3H, s, CH3C=N), 2.05 (3H, s, CH3C = N), 2.46 (3H, s, SMe), 3.84 (3H, s, CO2Me), 4.00 (3H, s, NOCH3), 5.08 (2H, s, OCH2), 5.52 (1 H, q, CHMe), 7.16 (1 H, m, ArH), 7.30-7.4 (3H, m, ArH), 7.59 (2H, m, ArH) and 7.88 (2H, d, ArH).

Compound 102 (isomeric mixture) 1H N. M. R. (CDCl3) # (ppm) 1.62 (3H, d, CH3CH), 1.84-2.05 (6H, m, 2 x CH3C=N), 2.50-2.55 (3H, m, SMe), 3.85 (3H, m, OMe), 4.04 (3H, m, NOMe), 5.05 (2H, m, ArCH2O), 5.55 (1H, q, CHCH3), 7.10-8.10 (8H, m, ArH).

Compound 103 (isomeric mixture) 1 H N. M. R. (CDCI3) 6 (ppm) 1.65 (3H, m, CH3CH), 1.78-2.10 (6H, m, 2 x CH3C=N), 2.20-2.45 (3H, m, SMe), 3.80-3.85 (3H, m, OMe), 4.00-4.05 (3H, m, NOMe), 5.05-5.10 (2H, m, ArCH2O), 5.60 (1H, m, CHCH3), 7.10-8.25 (8H, m, ArH).

Compound 104 1 H N. M. R. (CDCl3) 8 (ppm) 1.62 (3H, d, CHMe), 1.88 (3H, s, CH3C=N), 2.05 (3H, s, CH3C=N), 2.40 (3H, s, ArCH3), 2.45 (3H, s, SMe), 3.82 (3H, s, C02Me), 4.04 (3H, s, NOCH3), 5.08 (2H, s, OCH2), 5.60 (1H, q, CHMe), 7.18 (1H, m, ArH), 7.25 (1 H, m, ArH), 7.30-7.50 (4H, m, ArH) and 7.95 (2H, d, ArH).

Compound 105 (isomeric mixture) 1 H N. M. R. (CDCI3) 8 (ppm) 1.65 (3H, m, CH3CH), 1.95-2.10 (12H, m, 2 x CH3C=N, 2 x ArCHg), 2.42 (3H, s, SMe), 3.85 (3H, br. s, OMe), 4.05 (3H, br. s, NOMe), 5.08 (2H, m, ArCH2O), 5.30 (1H, m, CHCH3), 7.18-7.50 (7H, m, ArH).

Compound 106 (isomeric mixture) 1 H N. M. R. (CDCig) 8 (ppm) 2.08 (3H, s, CH3C = N), 2.10 (3H, s, CH3C=N), 2.50 and 2.55 (3H, 2 x s, SMe), 3.68 (1 H, d, SCH2), 3.80 (1 H, d, SCH2), 3.84 (3H, s, CO2Me), 4.04 (3H, s, NOMe), 5.10 (2H, s, OCH2), 5.18 (1H, m, CH=CH2), 5.30 (1H, d, CH=CH2), 5.95 (1H, m, CH=CH2), 7.18 (1H, m, ArH) and 7.35-7.50 (3H, m, ArH).

Compound 107 (isomeric mixture) 1 H N. M. R. (CDC13) 8 (ppm) 1.60 (3H, m, CH3CH), 1.85-2.05 (6H, m, 2 x CH3C=N), 2.45 (3H, s, SMe), 3.82 (3H, m, OMe), 4.02 (3H, m, NOMe), 5.08 (2H, m, ArCH2O), 5.55 (1H, m, CHCH3), 7.15-7.95 (9H, m, ArH).

Compound 108 (isomeric mixture) 1 H N. M. R. (CDC13) 5 (ppm) 2.05-2.15 (6H, m, 2xCH3C=N), 2.45-2.65 (3H, s, SMe), 3.85 (3H, m, CO2Me), 4.04 (3H, m, NOMe), 4.18 and 4.40 (2H, 2 x s, SCH2), 5.10 (2H, s, OCH2), 7.18 (1H, m, ArH) and 7.35-7. 68 (7H, m, ArH).

Compound 109 (isomeric mixture) 1 H N. M. R. (CDC13) 8 (ppm) 2.05-2.15 (6H, m, 2xCH3C=N), 2.25 (6H, s, 2xArMe), 2.44-2.55 (3H, m, SMe), 3.82-3.85 (3H, m, C02Me), 4.02-4.05 (3H, s, NOMe), 4.20-4.32 (2H, m, SCH2), 5.08-5.10 (2H, s, OCH2), 7.05-7.20 (4H, m, ArH) and 7.35-7.50 (3H, m, ArH).

Compound 110 (isomeric mixture) 1 H N. M. R. (CDCI3) ã (ppm) 2.02-2.08 (6H, m, 2 x CH3C=N), 2.20-2.30 (1H, 2 x t, alkyne CH), 2.45-2.60 (3H, m, SMe), 3.75 and 3.88 (1H, d, CH2), 3.82 (3H, m, OMe), 4.05 (3H, m, NOMe), 5.08 (2H, m, ArCH2O), 5.60 (1 H, m, CHCH3), 7.15-7.50 (4H, m, ArH).

Compound 11 1 (isomeric mixture) 1 H N. M. R. (CDCl3) 5 (ppm) 1.30-1.35 (3H, m, OCH2CH3), 1.60-1. 75 (3H, m, CH3CH), 1.70-2.10 (6H, m, 2 x CH3C=N), 2.45-2.65 (3H, m, SMe), 4.05 (3H, m, NOMe), 4.25-4.35 (2H, m, OCH2CH3), 5.05-5.10 (2H, m, ArCH2O), 5.40- 5.50 (1 H, m, CHCH3) and 7.00-7.55 (7H, m, ArH).

Compound 112 (isomeric mixture) 1H N. M. R. (CDCI3) ã (ppm) 1.25-1.35 (3H, m, OCH2CH3), 1.60-1.65 (3H, m, CH3CH), 1.90-2.10 (6H, m, 2 x CH3C=N), 2.45-2.55 (3H, m, SMe), 3.90 (3H, s, ArOMe), 4.00 (3H, m, NOMe), 4.25-4.35 (2H, m, OCH2CH3), 5.10 (2H, s, ArCH20), 5.25-5.65 (1H, m, CHCH3) and 6.90-8.05 (8H, m, ArH).

Compound 113 (isomeric mixture) 1 H N. M. R. (CDC13) 8 (ppm) 1.25-1.35 (3H, m, OCH2CH3), 1.60-1.70 (3H, m, CH3CH), 1.80-2.15 (6H, m, 2 x CH3C=N), 2.45-2.55 (3H, m, SMe), 4.00 (3H, s, NOMe), 4.25-4.35 (2H, m, OH2CH3), 5.10-5.15 (2H, m, ArCH20), 5.20-5.60 (1 H, m, CHCH3) and 7.10-8.00 (8H, m, ArH).

Compound 114 (isomeric mixture) 1 H N. M. R. (CDCl3) 8 (ppm) 1.25-1.35 (3H, m, OCH2CH3), 1.65-1.70 (3H, m, CH3CH), 1.90-2.15 (6H, m, 2 x CH3C=N), 2.40-2.50 (3H, m, SMe), 4.00 (3H, s, NOMe), 4.25-4.35 (2H, m, OCH2CH3), 5.10 (2H, s, ArCH20), 5.15-5.40 (1H, m, CHCH3) and 7.15-8.50 (7H, m, ArH).

Compound 115 (isomeric mixture) 1 H N. M. R. (CDC13) 8 (ppm) 1.25-1.35 (3H, m, OCH2CH3), 1.65-1.70 (3H, m, CH3CH), 1.85-2.20 (6H, m, 2 x CH3C=N), 2.45-2.55 (3H, m, SMe), 4.05 (3H, s, NOMe), 4.25-4.35 (2H, m, OCH2CH3), 5.05-5.10 (2H, m, ArCH20), 5.50-5.60 (1H, m, CHCH3) and 7.15-8.15 (8H, m, ArH).

Compound 116 (isomeric mixture) 1H N. M. R. (CDC13) a (ppm) 1.25-1.35 (3H, m, OCH2CH3), 1.65-1.70 (3H, m, CH3CH), 1.95-2.20 (6H, m, 2 x CH3C=N), 2.40-2.50 (3H, m, SMe), 4.00 (3H, s, NOMe), 4.25-4.35 (2H, m, OCH2CH3), 4.90-5.15 (1 H, m, CHCH3), 5.10 (2H, s, ArCH20) and 6.85-7.50 (7H, m, ArH).

Compound 1 17 (isomeric mixture) 1 H N. M. R. (CDC13) ã (ppm) 1.25-1.35 (3H, m, OCH2CH3), 1.60-1.65 (3H, m, CH3CH), 1.90-2.20 (6H, m, 2 x CH3C=N), 2.45-2.55 (3H, m, SMe), 4.05 (3H, s, NOMe), 4.25-4.35 (2H, m, OCH2CH3), 5.10 (2H, s, ArCH20), 5.50-5.60 (1H, m, CHCH3), 6.05 (2H, s, CH2) and 6.80-7.70 (7H, m, ArH).

Compound 1 18 (isomeric mixture) 1 H N. M. R. (CDCi3) 8 (ppm) 1.25-1.35 (3H, m, OCH2CH3), 1.60-1.65 (3H, m, CH3CH), 1.95-2.20 (6H, m, 2 x CH3C=N), 2.45-2.50 (3H, m, SMe), 4.00 (3H, s, NOMe), 4.25-4.35 (2H, m, OCH2CH3), 4.95-5.40 (1H, m, CHCH3), 5.10 (2H, m, ArCH2O) and 7.15-7.75 (8H, m, ArH).

Compound 1 19 (isomeric mixture) 1 H N. M. R. (CDC13) 8 (ppm) 1.30-1.35 (3H, m, OCH2CH3), 1.60-1.65 (3H, m, CH3CH), 1.90-2.20 (6H, m, 2 x CH3C=N), 2.45-2.55 (3H, m, SMe), 4.00 (3H, s, NOMe), 4.25-4.35 (2H, m, OCH2CH3), 5.10 (2H, s, ArCH2O), 5.15 (2H, s, ArCH2OAr), 5.25-5.60 (1H, m, CHCH3) and 6.95-8.00 (13H, m, ArH).

Compound 120 (isomeric mixture) 1 H N. M. R. (CDC13) 8 (ppm) 1.25-1.35 (3H, m, OCH2CH3), 1.60-1.65 (3H, m, CH3CH), 1.90-2.20 (6H, m, 2 x CH3C = N), 2.50-2.60 (3H, m, SMe), 4.00 (3H, s, NOMe), 4.25-4.35 (2H, m, OCH2CH3), 5.10 (2H, s, ArCH2O), 5.45-5.55 (1H, m, CHCH3) and (7H, m, ArH).

Compound 121 (isomeric mixture) 1 H N. M. R. (CDC13) 5 (ppm) 1.25-1.35 (3H, m, OCH2CH3), 1.60-1.70 (3H, m, CH3CH), 1.80-2.10 (6H, m, 2 x CH3C=N), 2.45-2.55 (3H, m, SMe), 4.05 (3H, m, NOMe), 4.25-4.35 (2H, m, OCH2CH3), 5.05-5.10 (2H, m, ArCH2O), 5.30- 5.70 (1 H, m, CHCH3) and 7.10-8.05 (9H, m, ArH).

Compound 122 (isomeric mixture) 1 H N. M. R. (CDC13) 8 (ppm) 1.25-1.35 (3H, m, OCH2CH3), 1.60-1.70 (3H, m, CH3CH), 1.80-2.10 (6H, m, 2 x CH3C=N), 2.50-2.55 (3H, m, SMe), 4.00-4.05 (3H, m, NOMe), 4.25-4.40 (2H, m, OCH2CH3), 5. 05-5.10 (2H, s, ArCH2O), 5.20-5.30 (1 H, m, CHCH3) and 7.05-7.55 (7H, m, ArH).

Compound 129 (isomeric mixture) 1H N. M. R. (CDC13) 5 (ppm) 1.26-1.38 (3H, m, OCH2CH3), 1.64-2.08 (12H, m, 2 x CH3C=N, 2 x CH3), 2.40-2.64 (3H, m, SMe), 4.04-4.08 (3H, m, NOMe), 4.10- 4.37 (2H, m, OCH2CH3), 5.10-5.16 (2H, m, ArCH2O) and 7.16-8.10 (9H, m, ArH).

Compound 131 (isomeric mixture) 1H N. M. R. (CDC13) 5 (ppm) 0.92-1.01 (3H, m, CH2CH3), 1.14-1.24 (3H, m, OCH2CH3), 1.80-2.14 (8H, m, 2 x CH3C=N, CH2CH3), 2.18-2.52 (3H, m, SMe), 3.93-3.96 (3H, m, NOMe), 4.00-4.32 (2H, m, OCH2CH3), 5.02-5.07 (2H, m, ArCH2O), 5.42 (1 H, t, CHCH2) and 7.08-7.92 (8H, m, ArH).

Compound 132 (isomeric mixture) 1 H N. M. R. (CDCl3) 5 (ppm) 0.98-1.10 (3H, m, CH2CH3), 1.23-1.36 (3H, m, OCH2CH3), 1.82-2.20 (8H, m, 2 x CH3C=N, CH2CH3), 2.43-2.53 (3H, m, SMe), 3.98-4.00 (3H, m, NOMe), 4.06-4.36 (2H, m, OCH2CH3), 5.04-5.12 (2H, m, ArCH2O), 5.58 (1H, t, CHCH2) and 7.14-8.02 (9H, m, ArH).

Compound 133 (isomeric mixture) 1 H N. M. R. (CDC13) 8 (ppm) 2.05-2.10 (3H, m, 2 x CH3C=N), 2.20-2.45 (3H, m, SMe), 3.82 (3H, m, OMe), 4.00 (3H, m, NOMe), 4.65 (2H, m, SCH2), 5.15 (2H, m, ArCH2O), 7.10-7.78 (18H, m, ArH).

Compound 134 (isomeric mixture-present as enol tautomer) 1H N. M. R. (CDC13) 5 (ppm) 2.05-2.10 (3H, m, 2 x CH3C=N), 2.18 (3H, s, C (Me) =COH), 2.48 (3H, m, SMe), 3.80-3.82 (3H, m, OMe), 3.98-4.00 (3H, m, NOMe), 4.95 (1H, s, OH), 5.15 (2H, m, ArCH2O), 7.10-7.88 (13H, m, ArH).

Compound 135 (isomeric mixture) 1H N. M. R. (CDCl3) # (ppm) 2.18-2.20 (3H, m, CH3C = N), 2.45-2.50 (6H, m, 2 x SMe), 3.80-3.82 (3H, m, OMe), 4.05 (3H, m, NOMe), 4.95-5.10 (2H, m, ArCH2O) and 7.10-7.78 (9H, m, ArH).

Compound 136 (isomeric mixture) 1H N. M. R. (CDC13) 6 (ppm) 1.28-1.40 (3H, m, SCH2CH3), 2.18-2.20 (3H, m, CH3C=N), 2.45-2.50 (3H, m, SMe), 2.95-3.05 (2H, m, SCH2CH3), 3.80-3.82 (3H, m, OMe), 4.05 (3H, m, NOMe), 4.95-5.10 (2H, m, ArCH2O) and 7.10-7.80 (9H, m, ArH).

Example 3 <BR> <BR> <BR> <BR> 2-Methoxvimino-N-methvl-2-[(f [(1-methyl-2-{[1-methylthio-1-([1-(3-<BR> <BR> <BR> <BR> <BR> <BR> chlorobenzoyl) ethyllthio) methylidenelhydrazono} propylidene) aminol- oxy} methyl) phenyllacetamide (Compound 220) A solution of methylamine (5 ml of 33% solution in ethanol) was added to a solution of compound 113 (see Table 2) (1.22 g) in tetrahydrofuran (5 ml) at 0°C.

After 30 minutes, the solvent was removed to give a residue which was triturated with diethyl ether/light petroleum (b. p. 40-60°C) to give the title compound as a solid.

The following compounds (see Table 3) of formula le, i. e. compounds of general formula I where X is NH, Y is N, W is methoxy, R2, R4 and R6 are methyl and q is 0, were prepared from the corresponding compound of formula Id (see Table 2) using methods analogous to Example 3.

Table 3 Compound m.p./°CR3 201 Me 3-methylbenzyl oil 202 Me 3-CF3-benzyl oil 1-(4-Br-benzoyl)ethyloil203Me 4-methylbenzyloil204Me 3,4-dimethylbenzyloil205Me 206 Me 1- (4-F-benzoyl) ethyl oil 1-(3-CF3-benzoyl)ethyloil207Me 209 Me 1- (4-Me-benzoyl) ethyl oil 1-(2,4-DiMe-benzoyl)ethyloil210Me 211 Me allyl oil 212 Me 1- (4-Me0-benzoyt) ethyl oil 213 Me 1- (3, 4-methylenedioxybenzoyl) ethyl oil 214 Me 1- [ (4-benzyloxy) benzoyllethyl oil 215 Me 1-benzoylethyl oil 216 Me 2-naphthoylmethyl 148-53 4-Cl-phenacyl55-60217Me 3,4-diCl-phenacyl112-5218Me 219 Me 1- (3, 5-diF-benzoyl) ethyl oil 1-(3-Cl-benzoyl)ethyloil220Me 221 Me 1-l2, 4-diCl-benzoyl) ethyl oil 222 Me 4-CN-phenacyl 124-8 223 Me phenacyl 126-9 224 Me 1-oxo-2-indanyl oil 225 Me 1-benzoyl-1-methylethyl 59-62 α-benzoylbenzyl72-5226Me 1-(4-CF3-benzoyl)ethyloil227Me 228 Me 1- (2-CF3-benzoyl) ethyl oil 229 Me 1-(3, 4-diCl-benzoyl) ethyl oil 230 Me 1- (2, 5-diF-benzoyl) ethyl oil Compound R1 R3 m. p./°C 231 Me 1- (4-CI-benzoyl) propyi 140-3 232 Me 1-benzoylpropyl 107-9 1-(4-Cl-benzoyl)ethyloil233Me 234 Ph 4-phenylbenzyl oil 235 Ph 1- (4-CI-benzoyl) ethyl oil 236 Ph methyl 109-11 237 Ph ethyl 107-9

The 1 H N. M. R. data of those compounds in Table 3 that were not solid at room temperature are presented below.

Compound 202 (isomeric mixture) 1 N. M. R. (CDC13) 5 (ppm) 2.06-2.15 (6H, m, 2xCH3C=N), 2.48-2.56 (3H, m, SMe), 2.90 (3H, d, NHMe), 3.95 (3H, m, NOMe), 4.28-4.40 (2H, m, SCH2), 5.10 (2H, m, OCH2), 6.70 (1 H, br s, NHMe), 7.16 (1 H, m, ArH) and 7.30-7.75 (7H, m, ArH).

Compound 204 (isomeric mixture) 1 H N. M. R. (CDC13) 5 (ppm) 2.05-2.10 (6H, m, 2xCH3C=N), 2.35 (3H, s, ArMe), 2.44-2.55 (3H, m, SMe), 2.85-2.95 (3H, m, NHCH3), 3.95 (3H, m, NOMe), 4.24- 4.35 (2H, m, SCH2), 5.12 (2H, m, OCH2), 6.72 (1 H, br s, NHMe), 7.10-7.32 (5H, m, ArH) and 7.35-7.50 (3H, m, ArH).

Compound 205 (isomeric mixture) 1H N. M. R. (CDCI3) 6 (ppm) 2.05-2.15 (6H, m, 2xCH3C=N), 2.25 (6H, s, 2xArMe), 2.46-2.56 (3H, s, SMe), 2.78-2.90 (3H, m, NHMe), 3.95 (3H, m, NOMe), 4.20-4.35 (2H, s, SCH2), 5.12 (2H, m, OCH2), 6.72 (1H, br s, NHCH3), 7.05-7.20 (4H, m, ArH) and 7.30-7.50 (3H, m, ArH).

Compound 211 (isomeric mixture) 1 H N. M. R. (CDCI3) 6 (ppm) 2.08-2.12 (6H, m, 2 x CH3C=N), 2.50-2.55 (3H, m, SMe), 2.80-2.90 (3H, m, NHMe), 3.65-3. 80 (2H, m, CH2S), 3.95 (3H, m, NOMe), 5.08 (2H, m, ArCH2O), 5.10-5.25 (2H, m, CH=CH2), 5.90 (1H, m, CH=CH2), 6.70 (1 H, m, NH), 7.18-7.50 (4H, m, ArH).

Compound 212 (isomeric mixture) 1H N. M. R. (CDC13) 8 (ppm) 1.60-1.70 (3H, m, CH3CH), 1.90-2.10 (6H, m, 2 x CH3C=N), 2.50-2.55 (3H, m, SMe), 2.90 (3H, d, CHgNH), 3.90 (3H, s, ArOCH3), 3.95 (3H, s, NOMe), 5.10 (2H, m, ArCH2O), 5.25-5.65 (1H, m, CH3CH), 6.65-6.75 (1H, br. m, NH) and 6.90-8.05 (8H, m, ArH).

Compound 213 (isomeric mixture) 1 H N. M. R. (CDC13) 6 (ppm) 1.60-1.65 (3H, m, CHgCH), 1.90-2.10 (6H, m, 2 x CH3C=N), 2.50-2.60 (3H, m, SMe), 2.85-2.90 (3H, m, CHgNH), 3.90 (3H, s, NOMe), 5.10 (2H, m, ArCH2O), 5.20-5.60 (1H, m, CH3CH), 6.05 (2H, s, OCH20), 6.65-6.80 (1H, br. m, NH) and 6.80-7.70 (7H, m, ArH).

Compound 214 (isomeric mixture) 1H N. M. R. (CDC13) 8 (ppm) 1.60-1.65 (3H, m, CH3CH), 1.90-2.10 (6H, m, 2 x CH3C=N), 2.45-2.60 (3H, m, SMe), 2.85-2.90 (3H, m, CH3NH), 3.95 (3H, s, NOMe), 5.10 (2H, m, ArCH2O), 5.15 (2H, s, ArCH20Ar), 5.25-5.65 (1H, m, CH3CH), 6.65-6.80 (1H, br. m, NH) and 6.95-8.00 (13H, m, ArH).

Compound 215 (isomeric mixture) I H N. M. R. (CDC13) 6 (ppm) 1.60-1. 70 (3H, m, CH3CH), 1.95-2.15 (6H, m, 2 x CH3C=N), 2.45-2. 60 (3H, m, SMe), 2.85-2.95 (3H, m, CH3NH), 3.90-4.00 (3H, m, NOMe), 5.05-5.15 (2H, m, ArCH2O), 5.30-5.65 (1H, m, CH3CH), 6.65-6.80 (1H, br. m, NH) and 7.10-8.05 (9H, m, ArH).

Compound 219 (isomeric mixture) 1 H N. M. R. (CDCI3) 6 (ppm) 1.58-1.66 (3H, m, CH3CH), 1.88-2.32 (6H, m, 2 x CH3C=N), 2.48-2.58 (3H, m, SMe), 2.90-2.95 (3H, m, CHgNH), 3.94-3.96 (3H, m, NOMe), 5.05-5.13 (2H, m, ArCH2O), 5.14-5.52 (1 H, m, CH3CH), 6.61-6.77 (1H, br. m, NH) and 6.98-7.60 (7H, m, ArH).

Compound 220 (isomeric mixture) 1 H N. M. R. (CDC13) 8 (ppm) 1.58-1.62 (3H, m, CH3CH), 1.82-2.10 (6H,-m, 2 x CH3C=N), 2.43-2.57 (3H, m, SMe), 2.82-2.86 (3H, m, CH3NH), 3.88-3.94 (3H, m, NOMe), 5.04-5.11 (2H, m, ArCH2O), 5.54 (1H, m, CH3CH), 6.61-6.77 (1H, br. m, NH) and 7.17-8.06 (8H, m, ArH).

Compound 221 (isomeric mixture) 1 H N. M. R. (CDC13) 6 (ppm) 1.62-1.68 (3H, m, CH3CH), 1.93-2.20 (6H, m, 2 x CH3C=N), 2.42-2.48 (3H, m, SMe), 2.91 (3H, d, CH3NH), 3.94 (3H, s, NOMe), 5.07-5.12 (2H, m, ArCH2O), 5.12-5.38 (1H, m, CH3CH), 6.64-6.79 (1H, br. m, NH) and 7.46-7.53 (7H, m, ArH).

Compound 224 (isomeric mixture) 1H N. M. R. (CDC13) 5 (ppm) 1.44-2.18 (6H, m, 2 x CH3C=N), 2.52-2.60 (3H, m, SMe), 2.84-2.94 (3H, m, CH3NH), 3.22-4.54 (3H, m, CH2 and CH), 3.88-3.95 (3H, m, NOMe), 5.02-5.14 (2H, m, ArCH2O), 5.14-5.52 (1H, m, CH3CH), 6.67- 6.81 (1H, br. m, NH) and 7.14-7.83 (8H, m, ArH).

Compound 227 (isomeric mixture) 1 H N. M. R. (CDCl3) # (ppm) 1.60-1.68 (3H, m, CH3CH), 1.83-2.20 (6H, m.'2 x CH3C=N), 2.47-2.58 (3H, m, SMe), 2.86-2.92 (3H, m, CH3NH), 3.92-3.98 (3H, m, NOMe), 5.04-5.11 (2H, m, ArCH2O), 5.23-5.60 (1 H, m, CH3CH), 6.64-6.76 (1H, br. m, NH) and 7.18-8.18 (8H, m, ArH).

Compound 228 (isomeric mixture) 1 H N. M. R. (CDCI3) 6 (ppm) 1.60-1.63 (3H, m, CH3CH), 1.92-2.19 (6H, m, 2 x CH3C=N), 2.21-2.27 (3H, m, SMe), 2.86-2.93 (3H, m, CHgNH), 3.92-3.96 (3H, m, NOMe), 4.96-5.40 (1H, m, CH3CH), 5.06-5.14 (2H, m, ArCH2O), 6.63-6.77 (1H, br. m, NH) and 7.16-7.76 (8H, m, ArH).

Compound 229 (isomeric mixture) 1H N. M. R. (CDCI3) 6 (ppm) 1.57-1.62 (3H, m, CH3CH), 1.87-2.31 (6H, m, 2 x CH3C=N), 2.46-2.57 (3H, m, SMe), 2.84-2.91 (3H, m, CH3NH), 3.90-3.97 (3H, m, NOMe), 5.06-5.14 (2H, m, ArCH2O), 5.43-5.56 (1H, m, CH3CH), 6.64-6.79 (1H, br. m, NH) and 7.17-8.16 (7H, m, ArH).

Compound 230 (isomeric mixture) 1H H N. M. R. (CDC13) 8 (ppm) 1.61-1.68 (3H, m, CH3CH), 1.79-2.22 (6H, m, 2 x CH3C=N), 2.44-2.57 (3H, m, SMe), 2.85-2.92 (3H, m, CHgNH), 3.90-3.98 (3H, m, NOMe), 5.03-5.11 (2H, m, ArCH2O), 5.22-5.31 (1 H, m, CH3CH), 6.63-6.77 (1H, br. m, NH) and 7.07-7.58 (7H, m, ArH).

Compound 233 (isomeric mixture-present as enol tautomer) 1H N. M. R. (CDC13) 8 (ppm) 1.90-2.80 (12H, m, 2 x CH3C=N, SMe, CMe=C), 2.90 (3H, d, CH3NH), 3.95 (3H, m, NOMe), (2H, m, CH2O), 6.70 (1H, m, NH) and 7.20-7.50 (8H, m, ArH).

Test Example Compounds were assessed for activity against one or more of the fotfowing: Erysiphe graminis f sp. tritici : barley powdery mildew Pyricularia oryzae : rice blast Leptosphaeria nodorum: glume blotch Plasmopara viticola: downy mildew of vines Aqueous solutions or dispersions of the compounds at the desired concentration, inciuding a wetting agent, were applied by spray or by drenching the stem base of the test plants, as appropriate. After a given time, plants or plant parts were inoculated with appropriate test pathogens and kept under controlled environmental conditions suitable for maintaining plant growth and development of the disease. After an appropriate time, the degree of infection of the affected part of the plant was visually estimated. Compounds are assessed on a score of 1 to 3 where 1 is little or no control, 2 is moderate control and 3 is good to total control.

At a concentration of 500 ppm (w/v) or less, the following compounds scored 2 or more against the fungi specified.

Erysiphe qraminis f sp. tritici 219-223,227,228,229, 236 and 237.

Pyricularia oryzae 135,136,212-215 and 217- 223.

Leptosphaeria nodorum 129,135,202,204-205,217- 223,224,225,226,227,228,229,230,236 and 237.

Plasmopara viticola 1-5,12-16,21-24,26,27,29,34,36,40,41,42,46,48,49,101,103,105 , 106,107,110,115,134,135 and 204-205.