Benzyl derivatives and pesticides containing them

The present invention relates to novel benzyl derivatives and pesticides for controlling pests, in particular fungi, insects, nematodes and spider mites. It is known that certain .beta.-methoxyacrylates (cf. European Patent 178,826) as well as certain oxime ethers (cf. European Patent 253,213) have fungicidal or insecticidal activity. However, their action is unsatisfactory.
We have found, surprisingly, that benzyl derivatives of the general formula I ##STR3## where A is CH.sub.2, CHCl, CH-C.sub.1 -C.sub.4 -alkyl, CH-C.sub.1 -C.sub.4 -alkoxy, CH-C.sub.1 -C.sub.4 -alkylthio or N-C.sub.1 -C.sub.4 -alkoxy,
B is OH, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylamino,
U, V and W are identical or different and are each hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,
D is ##STR4## where R' is hydrogen or C.sub.1 -C.sub.4 -alkyl,
R is hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.3 -C.sub.6 -halocycloalkyl, C.sub.3 -C.sub.6 -cycloalkyl-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted arylthio-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted aryloxy-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted aryl, unsubstituted or substituted aryl-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted hetaryl, unsubstituted or substituted hetaryl-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted hetaryloxy-C.sub.1 -C.sub.4 -alkyl or unsubstituted or substituted heterocyclyl, substituents being halogen, cyano, CO.sub.2 (C.sub.1 -C.sub.4 -alkyl), CO(C.sub.1 -C.sub.4 -alkyl), nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkoximino-C.sub.1 - or C.sub.2 -alkyl, aryl, aryloxy, benzyloxy, hetaryl, hetaryloxy, C.sub.3 -C.sub.6 -cycloalkyl, heterocyclyl or heterocyclyloxy, have an excellent fungicidal, insecticidal, nematicidal and ataritidal action which is better than that of the known .beta.-methoxyacrylates or oxime ethers. The fungicidal action is preferred.
The radicals stated for the general formula I may have, for example, the following meanings:
A may be C.sub.1 -C.sub.4 -alkylidene (e.g. methylidene, ethylidene, n-propylidene, isopropylidene, n-butylidene, isobutylidene, sec-butylidene or tert-butylidene), C.sub.1 -C.sub.4 -alkoxymethylidene (e.g. methoxy-, ethoxy-, n-propoxy-, isopropoxy-, n-butoxy-, isobutoxy-, sec-butoxy- or tert-butoxymethylidene), C.sub.1 -C.sub.4 -alkylthiomethylidene (e.g. methyl-, ethyl-, n-propyl-, isopropyl-, n-butyl-, isobutyl-, sec-butyl- or tert-butyl-thiomethylidene), C.sub.1 -C.sub.4 -alkoximino (e.g. methoximino, ethoximino, n-propoximino, isopropoximino, n-butoximino, isobutoximino, sec-butoximino or tert-butoximino or chloromethylidene,
B may be OH, C.sub.1 -C.sub.4 -alkoxy (e.g. methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy), C.sub.1 -C.sub.4 -alkylthio (e.g. methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio ) and C.sub.1 -C.sub.4 -alkylamino (e.g. methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino or tert-butylamino),
U, V and W may each be H, halogen (e.g. fluorine, chlorine, bromine or iodine), methyl or methoxy,
D may be ##STR5## R" may be hydrogen or C.sub.1 -C.sub.4 -alkyl (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl) and
R may be straight-chain or branched C.sub.1 -C.sub.10 -alkyl (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl or n-decyl), C.sub.3 -C.sub.6 -cycloalkyl (e.g. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl), C.sub.1 -C.sub.4 -haloalkyl (e.g. trifluoromethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, fluorodichloromethyl, difluorochloromethyl, chloromethyl, trichloromethyl, 2-chloroethyl, 2,2,2-trichloroethyl or pentachloroethyl), C.sub.3 -C.sub.6 -halocycloalkyl (e.g. 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-dichloro-3-methylcyclopropyl or tetrafluorocyclobutyl), C.sub.3 -C.sub.6 -cycloalkyl-C.sub.1 -C.sub.4 -allyl (e.g. 1-methylcyclopropyl, 2,2-dimethylcyclopropyl or 1-methylcyclohexyl), C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl (e.g. methoxymethyl, ethoxymethyl, n-propoxylmethyl, isopropoxylmethyl, n-butoxymethyl, isobutoxymethyl, sec-butoxymethyl, tert-butoxymethyl, 2-methoxyprop-2-yl, 2-ethoxyprop-2-yl, 2-n- or isopropoxprop-2-yl, 2-n-, iso-, sec- or tert-butoxyprop-2-yl), C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.4 -alkyl (e.g. methylthiomethyl, ethylthiomethyl, n-propylthiomethyl, isopropylthiomethyl, n-butylthiomethyl, isobutylthiomethyl, sec-butylthiomethyl, tert-butylthiomethyl, 2-methylthioprop-2-yl, 2-ethylthioprop-2-yl, 2-n- or isopropylthioprop-2-yl, 2-n-, iso-, sec- or tert-butylthioprop-2-yl), aryl(phenyl)thio-C.sub.1 -C.sub.4 -alkyl (e.g. phenylthiomethyl or 2-chlorophenylthiomethyl), unsubstituted or substituted aryloxy-C.sub.1 -C.sub.4 -alkyl (e.g. phenoxymethyl), unsubstituted or substituted aryl (e.g. phenyl, naphthyl or anthryl), unsubstituted or substituted aryl-C.sub.1 -C.sub.4 -alkyl (e.g. benzyl, 1-phenethyl, 2-phenethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 2-methyl-3-phenylpropyl, 2-methyl-2-phenylpropyl or 4-phenylbutyl), unsubstituted or substituted hetaryl (e.g. pyridyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrimidinyl, 4-pyrimidinyl, 2-pyrimidinyl, thienyl, 2-thienyl, 3-thienyl, furyl, 2-furyl, 3-furyl, 1-pyrrolyl, 1-imidazolyl, 1,2,4-triazolyl, 1,3,4-triazolyl, 4-thiazolyl or 2-benzothiazolyl), unsubstituted or substituted hetaryl-C.sub.1 -C.sub.4 -alkyl (e.g. 2-pyridylmethyl or 3-pyridylmethyl), unsubstituted or substituted hetaryloxy-C.sub.1 -C.sub.4 -alkyl (e.g. furfurylmethoxy) or unsubstituted or substituted heterocyclyl (e.g. oxiranyl, 1-aziridinyl, 1-azetidinyl, 1-pyrrolidinyl, 2-tetrahydrofuryl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 1-piperidinyl, 1-morpholinyl, 1-piperazinyl, 1,3-dioxanyl or 3-tetrahydrothiopyranyl).
The radicals referred to as being unsubstituted or substituted above are substituted, apart from hydrogen, for example by fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoromethoxy, 1,1,2,2-tetrafluoroethoxy, methoximinomethyl, ethoximinomethyl, n-propoximinomethyl, n-butoximinomethyl n-pentyloximinomethyl, n-hexyloximinomethyl, allyloximinomethyl, benzyloximinomethyl, isopropoximinomethyl, isobutoximinomethyl, tert-butoximinomethyl, methylimino-1-ethyl, ethoximino-1-ethyl, n-propoximino-1-ethyl, n-butoximino-l-ethyl, n-pentyloximino-1-ethyl, n-hexyloximino-l-ethyl, allyloximino-1-ethyl, benzyloximino-1-ethyl, phenyl, phenoxy, benzyloxy, imidazol-1-yl, piperazin-1-yl, 4-morpholinyl, piperidin-1-yl, pyrid-2-yloxy, cyclopropyl, cyclohexyl, oxiranyl, 1,3-dioxan-2-yl, 1,3-dioxolan-2-yl or tetrahydropyran-2-yloxy.
Preferred compounds of the general formula I are those in which
A is CHCH.sub.3, CHCH.sub.2 CH.sub.3, CHOCH.sub.3 or NOCH.sub.3,
B is OCH.sub.3 or NHCH.sub.3,
U, V and W are each hydrogen,
R' is hydrogen and methyl or
D and R each have the meanings stated in claim 1.
Owing to the C.dbd.C or C.dbd.N double bonds, the novel compounds of the general formula I may be obtained in the preparation as E/Z isomer mixtures. These can be separated into the individual components in a conventional manner, for example by crystallization or chromatography. Both the individual isomeric compounds and mixtures thereof form subjects of the invention and can be used as pesticides.
The preparation of the compounds of the general formula I as claimed in claim 1 is carried out, for example, as described in Scheme 1. ##STR6##
The compounds of the general formula I where A is CH.sub.2, CH-Alkyl or CH-Alkoxy can be prepared, for example, from the ketoester 4 by a Wittig or Wittig-Horner reaction (cf. European Patents 348,766 or 178,826 or German Patent 3,705,389). The similar compounds 5 are obtained from the ketoesters 2 in the same manner.
In an alternative procedure, a compound of the formula 7 or 9 is condensed with a suitable reagent, for example with formaldehyde where A is CH.sub.2 (cf. German Patent 3,317,356), a) with an aldehyde (cf. D. M. Brown, J. Chem. Soc. (1948), 2147) or b) first with N,N-dimethylformamide dimethyl acetal followed by reaction with a Grignard reagent where A is CH-Alkyl (similarly to C. Jutz, Chem. Ber. 91 (1958), 1867), with a formate followed by alkylation where A is CH-O-Alkyl (cf. European Patent 178,826). Further preparation methods for the compounds of the formula 5 and I where A is CH-O-Alkyl are described in European Patent 178,826.
A further possibility for the preparation of the compounds of the formula I where A is CH-Alkyl and B is O-Alkyl is the reaction of ketene acetals with phenyl chlorocarbonates (cf. N. Slougui, G. Rousseau, Synth. Commun. 12 (5) (1982), 401-407).
For compounds of the general formula I where A is CH-S-Alkyl and A is CHCl, the preparation can be carried out by the methods from European Patent 244,077 or 310,954.
The intermediates of the formulae 3, 6 and 8 can be prepared from the compounds 2, 5 and 7 by halogenating the latter by known methods, for example with chlorine, bromine or N-bromosuccinimide in an inert solvent (e.g. CCl.sub.4 or cyclohexane) with exposure to, for example, an Hg vapor lamp or using a free radical initiator, such as dibenzoyl peroxide, or by introducing the radicals L, such as mesylate, tosylate, acetate or triflate, via suitable intermediates (L is halogen or OH).
The oxime ethers of the formula I where A is N-O-Alkyl can be prepared from 4 a) by reaction with an O-Alkylhydroxylamine hydrochloride or b) with hydroxylamine hydrochloride and subsequent alkylation with an alkylating agent (e.g. an alkyl iodide, dialkyl sulfate, etc.) (cf. German Patent 3,623,921).
Using the methods similar to that in European Patent 254,426, a phenylacetate of the formula 9 can be converted with a base (e.g. NaOMe, Nag, K tert-butylate, etc.) in a solvent (such as diethyl ether, toluene, tert-butanol, etc,) into its anion and can be oximated with a suitable nitrosating agent (such as methyl nitrite, amyl nitrite, tert-butyl nitrite, etc.). The resulting oximate is alkylated with an alkylating agent (e.g. an alkyl iodide or dialkyl sulfate).
The same methods can also be applied to the compounds of the formulae 2 and 7, and the resulting oxime ethers 5 can be converted in a known manner (European Patent 254,426) via the intermediates 6 (L is, for example, halogen) into the desired compounds I.
The novel compounds of the general formula I are obtained specifically by reacting a benzyl derivative having a suitable leaving group L (e.g. halogen) 6 with a carbonic acid salt 10 in an inert solvent or diluent. ##STR7##
Specifically, the novel compounds are obtained as follows: ##STR8## Trithiocarbonates 13 are obtained, for example, by reacting the metal salts 12 with the benzyl bromides 11 by methods similar to known ones (cf. for example Houben-Weyl, Vol. E 4, page 451 et seq. (1983)). ##STR9##
The dithiocarbonates 15 can be prepared, for example, by reacting the benzyl bromides 11 with the metal salts 14 by methods similar to known ones (cf. for example R. Degani, Synthesis, (1975), 365). ##STR10##
Dithiocarbamates of the type 17 are obtained, for example, in the reaction with the benzyl bromides 11 with the compounds 16 by methods similar to known ones (cf. for example Houben-Weyl, Vol. E 4, page 299 et seq. (1983)). ##STR11##
The dithiocarbonic acid derivatives 18 may be obtained by thermal or acid-catalyzed rearrangement from the dithiocarbonic acid derivatives 15 (cf. for example Houben-Weyl, Vol. E 4, page 133 et seq. (1983)). ##STR12##
The thiocarbonates 20 are prepared, for example, by reaction of the benzyl bromides 11 with thiocarbonates 19 analogously to known processes ( cf. for example Houben-Weyl Vol. E 4, page 108 et seq. (1983)). ##STR13##
Thiocarbamic acids 22 are accessible by reaction of the benzyl bromides 11 with metal salts 21 analogously to known processes (cf. for example Houben-Weyl, Vol. E 4, page 299 ( 1983)). ##STR14##
Carbonic diesters 24 are obtained by methods similar to known ones, by reacting the benzyl bromides 11 with carbonates 23 (cf. for example V. F. Pozdner, Zh. Org. Khim. 12 (1976), 1407). ##STR15##
The carbamates 26 are obtainable by methods similar to known ones, from the benzylbromides 11 and the phosphacarbamates 25 (cf. for example M. Aresta, JOC 53 (1988), 4153).
The carboxylic acid metal salts 12, 14, 16, 19, 21, 23 and 25 are known or can be prepared by methods known from the literature (cf. Houben-Weyl, Vol. E 4).
In the preparation processes described above, B is usually alkoxy and U, V and W are each usually H.
The compounds in which B is OH (28) can be prepared by methods known from the literature (Organikum 16th Edition, pages 415 and 622), from the compounds of the general formula I where B is O-Alkyl (27) (cf. Scheme 2): ##STR16##
The acyl chlorides 29 can be prepared from the resulting carboxylic acids 28 in a conventional manner (cf. Organikum 16th Edition, page 423 et seq. (1985)). The conversion of 29 into the amides 30 is carried out similarly to Organikum 16th Edition, page 412 (1985).
The thioesters 31 are obtained from the acyl chlorides 29 (similarly to Houben-Weyl, Vol. 8, page 464 et seq. (1952)).
Alternatively, the thioesters 31 can also be obtained from the acids 28 (similarly to Houben-Weyl, Vol. E5, page 855 et seq. (1985)).
The amides 30 can also be prepared from the esters 27 by methods known from the literature.
The preparation of the compounds of the general formulae 2 and 7 which are ortho-substituted by methyl on the aromatic moiety is known (B is O-Alkyl and U, V and W are each H; cf. European Patents 178,826 and 260,832).
The reactions described can be carried out, for example, in an inert solvent or diluent (e.g. acetone, acetonitrile, dimethylformamide, dimethyl sulfoxide or N-methylpyrrolidone) using a base (e.g. sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, sodium hydride or sodium methylate).
The reaction can also be carried out in a two-phase system (e.g. dichloromethane, water) with the addition of a suitable phase transfer catalyst (e.g. cetyltrimethylammoniumchloride or benzyltriethylammonium chloride).

EXAMPLES
Example 1
Methyl 2-methoximino-2-{2-[(methyl-4-methylphenylthiocarbamoylsulfonyl)-methyl]-phenyl}-acetate (compound No. 157 in Table 2)
A pinch of potassium iodide is added to a solution of 3.6 g (17.5 mmol) of sodium N-methyl-N-4-methylphenyldithiocarbamate and 5 g (17.5 mmol) of methyl 2-methoximino-2-(2'-bromomethyl)-phenylacetate in 50 ml of acetone and stirring is carried out for 15 hours at room temperature. Thereafter, the mixture is filtered under suction and the mother liquor is evaporated down. The residue is stirred in ether and filtered off under suction. 4.6 g (65%) of compound No. 157 (Table 2) remain as a colorless solid.
m.p.: 109.degree.-113.degree. C.
.sup.1 H-NMR (CDCl.sub.3 /TMS): .delta.=2.35; 3.72; 3.77; 3.97 (each s, 3H, CH.sub.3); 4.30 (br, 2H, CH.sub.2); 7.07-7.47 ppm (m, 8H, aryl-H).
Example 2
Preparation of compound 157, Table 4
1 g (2.5 mmol) of the compound prepared in Example 1 is heated with 50 ml of 40% strength N-methylamine solution for 2 hours at 40.degree. C. Extraction is then carried out three times with ether, and the combined organic phases are dried and evaporated down. 1 g of the N-methylamide compound (No. 157, Table 4) remains as a colorless solid.
.sup.1 H-NMR (CDCl.sub.3 /TMS): .delta.=2.35; 3.72; 3.88 (each s, 3H, CH.sub.3); 2.89 (d, 3H, NHCH.sub.3); 4.32, (s, 2H, CH.sub.2); 6.67 (br, 1H, NH); 7.05-7.43 ppm (m, 8H, aryl-H).
Example 3
Preparation of compound No. 157, Table 1
A pinch of potassium iodide is added to a solution of 1.4 g (7 mmol) of sodium N-methyl-N-4-methylphenyldithiocarbamate and 2 g (7 mmol) of methyl .alpha.-(2-bromomethylphenyl)-.beta.-methoxyacrylate in 50 ml of acetone and stirring is carried out for 16 hours at room temperature. Thereafter, the mixture is filtered under suction and the mother liquor is evaporated down. The remaining residue is chromatographed over silica gel using hexane/methyl tert-butyl ether. 1.2 g (43%) of compound No. 157 (Table 1) are obtained as a colorless solid.
mp.: 98.degree.-99.degree. C.
.sup.1 H-NMR (CDCl.sub.3 /TMS): .delta.=2.33; 3.57; 3.74 (each s, 3H, CH.sub.3); 4.35 (s, 2H, CH.sub.2); 7.05-7.43 (m, 8H, aryl-H); 7.51 (s, 1H, .dbd.CH).
Example 4
Preparation of 2-hydroxymethyl-.alpha.-methoxyiminophenylacetic acid monomethylamide
A mixture of 57 g (200 mmol) of methyl 2-methoximino-2-(2-bromomethyl)phenylacetate, 29 g (300 mmol) of potassium acetate and a spatula tip of potassium iodide is heated in 300 ml of dimethylformamide for 30 minutes at 90.degree. C. After the mixture has cooled it is stirred into ice water. The precipitate is filtered with suction, washed with water and dried; colorless crystals, mp. 70.degree.-72.degree. C., yield 50 g (94% of theory).
The compound thus obtained (50 g/188 mmol) is dissolved in 500 ml of THF, 100 ml (1.12 mol) of 40% strength aqueous methylamine solution are added and the mixture is stirred for 22 hours at room temperature. The mixture is evaporated down, and the residue is taken up in ethyl acetate, washed twice with saturated sodium chloride solution, dried over magnesium sulfate and evaporated down. The oily residue gradually solidifies on standing; the product crystallizes on trituration with diisopropyl ether/ligroin. Beige-colored crystals, mp. 99.degree.-103.degree. C., yield 32 g (82% of theory).
.sup.1 H-NMR (CDCl.sub.3 /.delta.scale): 2.90 (d, 3H, NCH.sub.3); 3.48 (br t, 1H, OH); 2, 3H, OCH.sub.3); 4.40 (d, 2H, CH.sub.2 O); 7.05 (br, 1H, NH); 7.14 (dd, 1H) and 7.2-7.6 (m, 3H, aromatic protons)
IR (KBr, .about. in cm.sup.-1): 3384, 330.6, 3281, 1647, 1035
Example 5
Preparation of 2-(4-fluoroanilinocarbonyloxymethyl)-.alpha.-methoxyiminophenylacetic acid monomethylamide (Comp. 293, Tab. 4)
a) 2.2 g (10 mmol) of the compound obtained in Example 4, 1.4 g (10 mmol) of 4-fluorophenyl isocyanate and a spatula tip of 4-N,N-dimethylaminopyridine are stirred in 150 ml of toluene for 4 hours at 100.degree. C. The product precipitates out on cooling. It is filtered with suction, washed with toluene and dried. Colorless crystals, mp. 208.degree.-209.degree. C., yield 2.4 g (67% of theory). The compound is a 3:1 mixture of two rotamers.
.sup.1 H-NMR (CDCl.sub.3 /.delta. scale): 2.81 and 2.90 (2d, tog. 3H, NCH.sub.3 in both rotamers); 3.96 and 4.01 (2s, tog. 3H, OCH.sub.3); 5.08 and 5.36 (2s, tog. 2H, OCH.sub.2); 6.7-7.5 (several multiplets, tog. 10H, aromatic protons and both NH).
b) 2.2 g (10 mmol) of the compound obtained in Example 4 were suspended in 200 ml of toluene and heated to 60.degree. C.; first 1.74 g (10 mmol) of 4-fluorophenyl chloroformate and then 1.5 ml (1.1 g/10 mmol) of triethylamine were added dropwise. The mixture was stirred for 2 hours and allowed to cool, the precipitate was filtered with suction, the filtrate was washed several times with water, dried over magnesium sulfate and evaporated down. 3.0 g (83% of theory) of the compound (No. 293; Tab. 4) were obtained.
The compounds shown in the Tables below are prepared according to the Examples described.
TABLE 1__________________________________________________________________________ ##STR17##No. D R' R phys. data.sup.a)__________________________________________________________________________ 1 SC(S)NR'R CH.sub.3 methyl 2 SC(S)NR'R CH.sub.3 ethyl 3 SC(S)NR'R CH.sub.3 n-propyl 4 SC(S)NR'R CH.sub.3 tert.-butyl 5 SC(S)NR'R CH.sub.3 cyclopropyl 6 SC(S)NR'R CH.sub.3 cyclohexyl 3.70, 3.85 (3H), 4.50 (2H), 7.63 (1H) 7 SC(S)NR'R CH.sub.3 methoxymethyl 8 SC(S)NR'R CH.sub.3 phenoxymethyl 9 SC(S)NR'R CH.sub.3 methylthiomethyl 10 SC(S)NR'R CH.sub.3 phenyl 3.55; 3.71; 3.76 (3 .times. 3H); 4.37 (2H); 7.03-7.40 (9H); 7.51 (1H) 11 SC(S)NR'R CH.sub.3 2-fluorophenyl 12 SC(S)NR'R CH.sub.3 3-fluorophenyl 102-106.degree. C. 13 SC(S)NR'R CH.sub.3 4-fluorophenyl 3.57; 3.73; 3.74 (3 .times. 3H); 4.35 (2H); 7.04-7.43 (8H), 7.51 (1H) 14 SC(S)NR'R CH.sub.3 pentafluorophenyl 15 SC(S)NR'R CH.sub.3 2-chlorophenyl 16 SC(S)NR'R CH.sub.3 3-chlorophenyl 3.57; 3.72; 3.74 (3 .times. 3H); 4.34 2H); 7.04-7.43 (8H); 7.51 (1H) 17 SC(S)NR'R CH.sub.3 4-chlorophenyl 3.00, 3.71, 3.86 (3H), 4.35 (2H) 18 SC(S)NR'R CH.sub.3 pentachlorophenyl 19 SC(S)NR'R CH.sub.3 2,3-dichlorophenyl 20 SC(S)NR'R CH.sub.3 2,4-dichlorophenyl 21 SC(S)NR'R CH.sub.3 2,5-dichlorophenyl 22 SC(S)NR'R CH.sub.3 2,6-dichlorophenyl 23 SC(S)NR'R CH.sub.3 3,4-dichlorophenyl 24 SC(S)NR'R CH.sub.3 3,5-dichlorophenyl 25 SC(S)NR'R CH.sub.3 2,3,4-trichlorophenyl 26 SC(S)NR'R CH.sub.3 2,3,5-trichlorophenyl 27 SC(S)NR'R CH.sub.3 2,3,6-trichlorophenyl 28 SC(S)NR'R CH.sub.3 2,4,5-trichlorophenyl 29 SC(S)NR'R CH.sub.3 2,4,6-trichlorophenyl 30 SC(S)NR'R CH.sub.3 3,4,5-trichlorophenyl 31 SC(S)NR'R CH.sub.3 2,3,4,6-tetrachlorophenyl 32 SC(S)NR'R CH.sub.3 2,3,5,6-tetrachlorophenyl 33 SC(S)NR'R CH.sub.3 2-bromophenyl 34 SC(S)NR'R CH.sub.3 3-bromophenyl 35 SC(S)NR'R CH.sub.3 4-bromophenyl 36 SC(S)NR'R CH.sub.3 2,4-dibromophenyl 37 SC(S)NR'R CH.sub.3 3-bromo-4-fluorophenyl 38 SC(S)NR'R CH.sub.3 3-bromo-4-methoxyphenyl 39 SC(S)NR'R CH.sub.3 2-iodophenyl 40 SC(S)NR'R CH.sub.3 3-iodophenyl 41 SC(S)NR' R CH.sub.3 4-iodophenyl 42 SC(S)NR'R CH.sub.3 2-chloro-4-fluorophenyl 43 SC(S)NR'R CH.sub.3 2-chloro-5-fluorophenyl 44 SC(S)NR'R CH.sub.3 2-chloro-6-fluorophenyl 45 SC(S)NR'R CH.sub.3 2-chloro-4-bromophenyl 46 SC(S)NR'R CH.sub.3 2-bromo-4-chlorophenyl 47 SC(S)NR'R CH.sub.3 2-bromo-4-fluorophenyl 48 SC(S)NR'R CH.sub.3 3-bromo-4-fluorophenyl 49 SC(S)NR'R CH.sub.3 3-chloro-4-fluorophenyl 50 SC(S)NR'R CH.sub.3 3-fluoro-4-chlorophenyl 51 SC(S)NR'R CH.sub.3 2-cyanophenyl 52 SC(S)NR'R CH.sub.3 3-cyanophenyl 53 SC(S)NR'R CH.sub.3 4-cyanophenyl 54 SC(S)NR'R CH.sub.3 2-nitrophenyl 55 SC(S)NR'R CH.sub.3 3-nitrophenyl 56 SC(S)NR'R CH.sub.3 4-nitrophenyl 57 SC(S)NR'R CH.sub.3 2-methylphenyl 2.17; 3.54; 3.69; 3.71; (4 .times. 3H); 4.35 (2H); 7.03-7.41 (8H); 7.51 (1H) 58 SC(S)NR'R CH.sub.3 3-methylphenyl 2.34; 3.65; 3.72; 3.74; (4 .times. 3H); 4.36 (2H); 7.00-7.51 (8H); 7.43 (1H) 59 SC(S)NR'R CH.sub.3 4-methylphenyl 98-99.degree. C. 60 SC(S)NR'R CH.sub.3 2,4-dimethylphenyl 61 SC(S)NR'R CH.sub.3 2,6-dimethylphenyl 120-121.degree. C. 62 SC(S)NR'R CH.sub.3 3,4-dimethylphenyl 63 SC(S)NR' R CH.sub.3 3,5-dimethylphenyl 64 SC(S)NR'R CH.sub.3 2,3,4-trimethylphenyl 65 SC(S)NR'R CH.sub.3 2,3,5-trimethylphenyl 66 SC(S)NR'R CH.sub.3 2,3,6-trimethylphenyl 67 SC(S)NR'R CH.sub.3 2,4,5-trimethylphenyl 68 SC(S)NR'R CH.sub.3 2,4,6-trimethylphenyl 69 SC(S)NR'R CH.sub.3 3,4,5-trimethylphenyl 70 SC(S)NR'R CH.sub.3 pentamethylphenyl 71 SC(S)NR'R CH.sub.3 2-ethylphenyl 72 SC(S)NR'R CH.sub.3 3-ethylphenyl 73 SC(S)NR'R CH.sub.3 4-ethylphenyl 74 SC(S)NR'R CH.sub.3 3,5-diethylphenyl 75 SC(S)NR'R CH.sub.3 2-n-propylphenyl 76 SC(S)NR'R CH.sub.3 3-n-propylphenyl 77 SC(S)NR'R CH.sub.3 4-n-propylphenyl 78 SC(S)NR'R CH.sub.3 2-isopropylphenyl 79 SC(S)NR'R CH.sub.3 3-isopropylphenyl 80 SC(S)NR'R CH.sub.3 4-isopropylphenyl 81 SC(S)NR'R CH.sub.3 2,4-diisopropylphenyl 82 SC(S)NR'R CH.sub.3 3,5-diisopropylphenyl 83 SC(S)NR'R CH.sub.3 4-n-butyphenyl 84 SC(S)NR'R CH.sub.3 4-sec.-butylphenyl 85 SC(S)NR'R CH.sub.3 4-iso-butylphenyl 86 SC(S)NR'R CH.sub.3 4-tert.-butylphenyl 87 SC(S)NR'R CH.sub.3 3-tert.-butylphenyl 88 SC(S)NR'R CH.sub.3 2-tert.-butylphenyl 89 SC(S)NR'R CH.sub.3 2,4-di-tert.-butylphenyl 90 SC(S)NR'R CH.sub.3 3,5-di-tert.-butylphenyl 91 SC(S)NR'R CH.sub.3 4-n-hexylphenyl 92 SC(S)NR'R CH.sub.3 4-n-dodecylphenyl 93 SC(S)NR'R CH.sub.3 2-methyl-4-tert.-butylphenyl 94 SC(S)NR'R CH.sub.3 2-methyl-6-tert.-butylphenyl 95 SC(S)NR'R CH.sub.3 2-methyl-4-isopropylphenyl 96 SC(S)NR'R CH.sub.3 2-methyl-4-cyclohexylphenyl 97 SC(S)NR'R CH.sub.3 2-methyl-4-phenylphenyl 98 SC(S)NR'R CH.sub.3 2-methyl-4-benzylphenyl 99 SC(S)NR'R CH.sub.3 2-methyl-4-phenoxyphenyl100 SC(S)NR'R CH.sub.3 2-methyl-4-benzyloxyphenyl101 SC(S)NR'R CH.sub.3 2-methyl-3-chlorophenyl102 SC(S)NR'R CH.sub.3 2-methyl-4-chlorophenyl103 SC(S)NR'R CH.sub.3 2-methyl-5-chlorophenyl104 SC(S)NR'R CH.sub.3 2-methyl-6-chlorophenyl105 SC(S)NR'R CH.sub.3 2-methyl-4-fluorophenyl106 SC(S)NR'R CH.sub.3 2-methyl-3-bromophenyl107 SC(S)NR'R CH.sub.3 2-methyl-4-bromophenyl108 SC(S)NR'R CH.sub.3 2-methyl-3-methoxyphenyl109 SC(S)NR'R CH.sub.3 2-methyl-4-methoxyphenyl110 SC(S)NR'R CH.sub.3 2-methyl-5-methoxyphenyl111 SC(S)NR'R CH.sub.3 2-methyl-6-methoxyphenyl112 SC(S)NR'R CH.sub.3 2-methyl-4-isopropoxyphenyl113 SC(S)NR'R CH.sub.3 2-methyl-2,5-dimethoxyphenyl114 SC(S)NR'R CH.sub.3 2-methoxyphenyl115 SC(S)NR'R CH.sub.3 3-methoxyphenyl116 SC(S)NR'R CH.sub.3 4-methoxyphenyl117 SC(S)NR'R CH.sub.3 2,3-dimethoxyphenyl118 SC(S)NR'R CH.sub.3 2,4-dimethoxyphenyl119 SC(S)NR'R CH.sub.3 2,5-dimethoxyphenyl120 SC(S)NR'R CH.sub.3 2,6-dimethoxyphenyl121 SC(S)NR'R CH.sub.3 3,4-dimethoxyphenyl122 SC(S)NR'R CH.sub.3 3,5-dimethoxyphenyl123 SC(S)NR'R CH.sub.3 3,6-dimethoxyphenyl124 SC(S)NR'R CH.sub.3 2,3,4-trimethoxyphenyl125 SC(S)NR'R CH.sub.3 2,3,5-trimethoxyphenyl126 SC(S)NR'R CH.sub.3 2,3,6-trimethoxyphenyl127 SC(S)NR'R CH.sub.3 2,4,5-trichlorophenyl128 SC(S)NR'R CH.sub.3 2,4,6-trichlorophenyl129 SC(S)NR'R CH.sub.3 2,3,4,6-tetrachlorophenyl130 SC(S)NR'R CH.sub.3 2,3,5,6-tetrachlorophenyl131 SC(S)NR'R CH.sub.3 2-bromophenyl132 SC(S)NR'R CH.sub.3 3-bromophenyl133 SC(S)NR'R CH.sub.3 4-bromophenyl134 SC(S)NR'R CH.sub.3 2,4-dibromophenyl135 SC(S)NR'R CH.sub.3 3-bromo-4-fluorophenyl136 SC(S)NR'R CH.sub.3 3-bromo-4-methoxyphenyl137 SC(S)NR'R CH.sub.3 2-iodophenyl138 SC(S)NR'R CH.sub.3 3-iodophenyl139 SC(S)NR'R CH.sub.3 4-iodophenyl140 SC(S)NR'R CH.sub.3 2-chloro-4-fluorophenyl141 SC(S)NR'R CH.sub.3 2-chloro-5-fluorophenyl142 SC(S)NR'R CH.sub.3 2-chloro-6-fluorophenyl143 SC(S)NR'R CH.sub.3 2-chloro-4-bromophenyl144 SC(S)NR'R CH.sub.3 2-bromo-4-chlorophenyl145 SC(S)NR'R CH.sub.3 2-bromo-4-fluorophenyl146 SC(S)NR'R CH.sub.3 3-bromo-4-chlorophenyl147 SC(S)NR'R CH.sub.3 3-chloro-4-fluorophenyl148 SC(S)NR'R CH.sub.3 3-fluoro-4-chlorophenyl149 SC(S)NR'R CH.sub.3 2-cyanophenyl150 SC(S)NR'R CH.sub.3 3-cyanophenyl151 SC(S)NR'R CH.sub.3 4-cyanophenyl152 SC(S)NR'R CH.sub.3 2-nitrophenyl153 SC(S)NR'R CH.sub.3 3-nitrophenyl154 SC(S)NR'R CH.sub.3 4-nitrophenyl155 SC(S)NR'R CH.sub.3 2-methylphenyl156 SC(S)NR'R CH.sub.3 3-methylphenyl157 SC(S)NR' R CH.sub.3 4-methylphenyl158 SC(S)NR'R CH.sub.3 2,4-dimethylphenyl159 SC(S)NR'R CH.sub.3 2,6-dimethylphenyl160 SC(S)NR'R CH.sub.3 3,4-dimethylphenyl161 SC(S)NR'R CH.sub.3 3,5-dimethylphenyl162 SC(S)NR'R CH.sub.3 2,3,4-trimethylphenyl163 SC(S)NR'R CH.sub.3 2,3,5-trimethylphenyl164 SC(S)NR'R CH.sub.3 2,3,6-trimethylphenyl165 SC(S)NR'R CH.sub.3 2,4,5-trimethylphenyl166 SC(S)NR'R CH.sub.3 2,4,6-trimethylphenyl167 SC(S)NR'R CH.sub.3 2,4,5-trimethylphenyl168 SC(S)NR'R CH.sub.3 pentamethylphenyl169 SC(S)NR'R CH.sub.3 2-ethylphenyl170 SC(S)NR'R CH.sub.3 3-ethylphenyl171 SC(S)NR'R CH.sub.3 4-ethylphenyl172 SC(S)NR'R CH.sub.3 3,5-diethylphenyl173 SC(S)NR'R CH.sub.3 2-n-propylphenyl174 SC(S)NR'R CH.sub.3 3-n-propylphenyl175 SC(S)NR'R CH.sub.3 4-n-propylphenyl176 SC(S)NR'R CH.sub.3 2,4,5-trimethoxyphenyl177 SC(S)NR'R CH.sub.3 2,4,6-trimethoxyphenyl178 SC(S)NR'R CH.sub.3 3,4,5-trimethoxyphenyl179 SC(S)NR'R CH.sub.3 2-ethoxyphenyl180 SC(S)NR'R CH.sub.3 3-ethoxyphenyl181 SC(S)NR'R CH.sub.3 4-ethoxyphenyl182 SC(S)NR'R CH.sub.3 2-isopropoxyphenyl183 SC(S)NR'R CH.sub.3 3-isopropoxyphenyl184 SC(S)NR'R CH.sub.3 4-isopropoxyphenyl185 SC(S)NR'R CH.sub.3 3-tert.-butoxyphenyl186 SC(S)NR'R CH.sub.3 4-tert.-butoxyphenyl187 SC(S)NR'R CH.sub.3 2-trifluoromethoxyphenyl188 SC(S)NR'R CH.sub.3 3-trifluoromethoxyphenyl189 SC(S)NR'R CH.sub.3 4-trifluoromethoxyphenyl190 SC(S)NR'R CH.sub. 3 3-(1',1',2',2'-tetrafluoro)-ethoxyphenyl191 SC(S)NR'R CH.sub.3 4-(1',1',2',2'-tetrafluoro)-ethoxyphenyl192 SC(S)NR'R CH.sub.3 2-chloromethylphenyl193 SC(S)NR'R CH.sub.3 3-chloromethylphenyl194 SC(S)NR'R CH.sub.3 4-chloromethylphenyl195 SC(S)NR'R CH.sub.3 2-trifluoromethylphenyl196 SC(S)NR'R CH.sub.3 3-trifluoromethylphenyl197 SC(S)NR'R CH.sub.3 4-trifluoromethylphenyl198 SC(S)NR'R CH.sub.3 2-(methoxyiminomethyl)-phenyl199 SC(S)NR'R CH.sub.3 3-(methoxyiminomethyl)-phenyl200 SC(S)NR'R CH.sub.3 4-(methoxyiminomethyl)-phenyl201 SC(S)NR'R CH.sub.3 2-(ethoxyiminomethyl)-phenyl202 SC(S)NR'R CH.sub.3 3-(ethoxyiminomethyl)-phenyl203 SC(S)NR'R CH.sub.3 4-(ethoxyiminomethyl)-phenyl204 SC(S)NR'R CH.sub.3 2-methyl-4-methoximinoethyl-phenyl205 SC(S)NR'R CH.sub.3 2-methyl-4-methoximinomethyl-phenyl206 SC(S)NR'R CH.sub.3 2,6-dimethyl-4-methoximinomethyl-phenyl207 SC(S)NR'R CH.sub.3 2,6-dimethyl-4-methoximinoethyl-phenyl208 SC(S)NR'R CH.sub.3 2-phenylphenyl209 SC(S)NR'R CH.sub.3 3-phenylphenyl210 SC(S)NR'R CH.sub.3 4-phenylphenyl211 SC(S)NR'R CH.sub.3 2-phenoxyphenyl212 SC(S)NR'R CH.sub.3 3-phenoxyphenyl213 SC(S)NR'R CH.sub.3 4-phenoxyphenyl214 SC(S)NR'R CH.sub.3 2-benzyloxyphenyl215 SC(S)NR'R CH.sub.3 3-benzyloxyphenyl216 SC(S)NR'R CH.sub.3 4-benzyloxyphenyl217 SC(S)NR'R CH.sub.3 4-(imidazol-1'-yl)phenyl218 SC(S)NR'R CH.sub.3 4-(piperazin-1'-yl)phenyl219 SC(S)NR'R CH.sub.3 4-(morpholin-1'-yl)phenyl220 SC(S)NR'R CH.sub.3 4-(piperidin-1'-yl)phenyl221 SC(S)NR'R CH.sub.3 4-(pyridyl-2' -oxy)phenyl222 SC(S)NR'R CH.sub.3 2-cyclopropylphenyl223 SC(S)NR'R CH.sub.3 3-cyclopropylphenyl224 SC(S)NR'R CH.sub.3 4-cyclopropylphenyl225 SC(S)NR'R CH.sub.3 3-cyclohexylphenyl226 SC(S)NR'R CH.sub.3 4-cyclohexylphenyl227 SC(S)NR'R CH.sub.3 4-oxiranylphenyl228 SC(S)NR'R CH.sub.3 4-(1',3'-dioxan-2'-yl)-phenyl229 SC(S)NR'R CH.sub.3 4-(tetrahydropyran-2-yl-oxy)-phenyl230 SC(S)NR'R CH.sub.3 1-naphthyl231 SC(S)NR'R CH.sub.3 2-naphthyl232 SC(S)NR'R CH.sub.3 benzyl 4.50 (CH.sub.2) amide rotamers233 SC(S)NR'R CH.sub.3 2-methylbenzyl234 SC(S)NR'R CH.sub.3 3-methylbenzyl235 SC(S)NR'R CH.sub.3 4-methylbenzyl236 SC(S)NR'R CH.sub.3 4-tert.-butylbenzyl 1.31 (9H), 4.50 (CH.sub.2) amide rotamers237 SC(S)NR'R CH.sub.3 2-chlorobenzyl238 SC(S)NR'R CH.sub.3 3-chlorobenzyl239 SC(S)NR'R CH.sub.3 4-chlorobenzyl240 SC(S)NR'R CH.sub.3 2-pyridyl241 SC(S)NR'R CH.sub.3 3-pyridyl242 SC(S)NR'R CH.sub.3 4-pyridyl243 SC(S)NR'R CH.sub.3 2,6-pyrimidinyl244 SC(S)NR'R CH.sub.3 1,5-pyrimidinyl245 SC(S)NR'R CH.sub.3 2-thienyl246 SC(S)NR'R CH.sub.3 3-thienyl247 SC(S)NR'R CH.sub.3 2-furyl248 SC(S)NR'R CH.sub.3 3-furyl249 SC(S)NR'R CH.sub.3 1-pyrrolyl250 SC(S)NR'R CH.sub.3 1-imidazolyl251 SC(S)NR'R CH.sub.3 1,2,4-triazolyl252 SC(S)NR' R CH.sub.3 1,3,4-triazolyl253 SC(S)NR'R CH.sub.3 4-thiazolyl254 SC(S)NR'R CH.sub.3 2-benzothiazolyl255 SC(S)NR'R CH.sub.3 2-pyridylmethyl256 SC(S)NR'R CH.sub.3 3-pyridylmethyl257 SC(S)NR'R CH.sub.3 4-pyridylmethyl258 SC(S)NR'R Et phenyl 1.26 (9H), 3.57, 3.72 (3H), 4.24 (2 .times. 2H)259 SC(S)NR'R Et 2-methylphenyl260 SC(S)NR'R Et 2-chlorophenyl261 SC(S)NR'R Et 4-methylphenyl 107-112.degree. C.262 SC(S)NR'R Et 2-naphtyl263 SC(S)SR -- CH.sub.3264 SC(S)SR -- CH.sub.2 -phenyl265 SC(S)SR -- phenyl266 SC(S)SR -- A* 3.67, 3.77 (3H), 4.55 (2H), 7.39 (1H)267 SC(S)OR -- CH.sub.3268 SC(S)OR -- phenyl269 SC(S)OR -- 2-CH.sub.3 -phenyl270 SC(S)OR -- 3-CH.sub.3 -phenyl 2.38, 3.71, 3.84 (3H), 4.39 (2H)271 SC(S)OR -- 4-CH.sub.3 -phenyl272 SC(S)OR -- 2-Cl-phenyl273 SC(S)OR -- 3-Cl-phenyl274 SC(S)OR -- 4-Cl-phenyl275 SC(S)OR -- CH.sub.2 -phenyl 1707, 1633, 1256, 1197, 1126, 1054276 SC(S)OR -- CH.sub.2 -(2-Me)-phenyl 2.35, 3.69, 3.81 (3H), 4.32, 5.63 (2H), 7.58 (1H)277 SC(S)OR -- CH.sub.2 -(3-Me)-phenyl278 SC(S)OR -- CH.sub.2 -(4-Me)-phenyl279 SC(S)OR -- CH.sub.2 -(2-Cl)-phenyl 1746, 1462, 1255, 1127, 1060280 SC(S)OR -- CH.sub.2 -(3-Cl)-phenyl281 SC(S)OR -- CH.sub.2 -(4-Cl)-phenyl282 OC(O)OR -- CH.sub.3283 OC(O)OR -- tert.-butyl284 OC(O)OR -- CH.sub.2 -phenyl285 OC(O)OR -- phenyl286 SC(S)NR'R CH.sub.3 3-Me, 4-F-phenyl 2.25; 3.57; 3.72; 3.75 (4 .times. 3H); 4.35 (2H); 7.00-7.41 (7H); 7.51 (1H)287 SC(S)NR'R H 2-phenyl-eth-2-yl 7.58 (1H) amide rotamers288 SCIS)NR'R Me 4-tert-butoxybenzyl 98-102.degree. C.289 SC(S)NR'R Et 3,4-(OCH.sub.2 O)phenyl 130-134.degree. C.290 SC(S)OR -- ethyl 1708, 1633, 1257, 1126, 1048291 SC(S)OR -- isopropyl 1707, 1632, 1250, 1226, 1224, 1089, 1037292 SC(S)OR -- 4-methoxybenzyl 3.70, 3.80, 3.83 (3H), 4.57 (2H), 7.58 (1H)293 SC(S)NR'R Me CH.sub.2 -(3-pyridyl) 1705, 1633, 1480, 1432, 1384, 1258, 1198, 1125, 989__________________________________________________________________________ ##STR18## .sup.a) IR (cm.sup.-1); .sup. 1 HNMR (CDCl.sub.3 /TMS); m. p.
TABLE 2__________________________________________________________________________ ##STR19##No. D R' R phys. data.sup.a)__________________________________________________________________________ 1 SC(S)NR'R CH.sub.3 methyl 2 SC(S)NR'R CH.sub.3 ethyl 3 SC(S)NR'R CH.sub.3 n-propyl 4 SC(S)NR'R CH.sub.3 tert.-butyl 5 SC(S)NR'R CH.sub.3 cyclopropyl 6 SC(S)NR'R CH.sub.3 cyclohexyl 2934, 1727, 1473, 1439, 1393, 1319, 1216, 1087, 1067, 1017 7 SC(S)NR'R CH.sub.3 methoxymethyl 8 SC(S)NR'R CH.sub.3 phenoxymethyl 9 SC(S)NR'R CH.sub.3 methylthiomethyl 10 SC(S)NR'R CH.sub.3 phenyl 3.75; 3.76; 3.95 (3 .times. 3H); 4.32(2H); 7.08-7.51 (9H); 11 SC(S)NR'R CH.sub.3 2-fluorophenyl 12 SC(S)NR'R CH.sub.3 3-fluorophenyl 3.73; 3.80; 3.99 (3 .times. 3H); 4.33 (2H); 6.95-7.50 (8H) 13 SC(S)NR'R CH.sub.3 4-fluorophenyl 3.72; 3.77; 3.97 (3 .times. 3H); 4.32 (2H); 7.07-7.48 (8H) 14 SC(S)NR'R CH.sub.3 pentafluorophenyl 15 SC(S)NR'R CH.sub.3 2-chlorophenyl 16 SC(S)NR'R CH.sub.3 3-chlorophenyl 3.72; 3.80; 3.97 (3 .times. 3H); 4.34 (2H); 7.10-7.49 (8H) 17 SC(S)NR'R CH.sub.3 4-chlorophenyl 2.91, 3.72, 4.05 (3H), 4.30 (2H), 6.57-7.40 ppm (8H) 18 SC(S)NR'R CH.sub.3 pentachlorophenyl 19 SC(S)NR'R CH.sub.3 2,3-dichlorophenyl 20 SC(S)NR'R CH.sub.3 2,4-dichlorophenyl 21 SC(S)NR'R CH.sub.3 2,5-dichlorophenyl 22 SC(S)NR'R CH.sub.3 2,6-dichlorophenyl 23 SC(S)NR'R CH.sub.3 3,4-dichlorophenyl 24 SC(S)NR'R CH.sub.3 3,5-dichlorophenyl 25 SC(S)NR'R CH.sub.3 2,3,4-trichlorophenyl 26 SC(S)NR'R CH.sub.3 2,3,5-trichlorophenyl 27 SC(S)NR'R CH.sub.3 .2,3,6-trichlorophenyl 28 SC(S)NR'R CH.sub.3 2,4,5-trichlorophenyl 29 SC(S)NR'R CH.sub.3 2,4,6-trichlorophenyl 30 SC(S)NR'R CH.sub.3 3,4,5-trichlorophenyl 31 SC(S)NR'R CH.sub.3 2,3,4,6-tetrachlorophenyl 32 SC(S)NR'R CH.sub.3 2,3,5,6-tetrachlorophenyl 33 SC(S)NR'R CH.sub.3 2-bromophenyl 34 SC(S)NR'R CH.sub.3 3-bromophenyl 35 SC(S)NR'R CH.sub.3 4-bromophenyl 36 SC(S)NR'R CH.sub.3 2,4-dibromophenyl 37 SC(S)NR'R CH.sub.3 3-bromo-4-fluorophenyl 38 SC(S)NR'R CH.sub.3 3-bromo-4-methoxyphenyl 39 SC(S)NR'R CH.sub.3 2-iodophenyl 40 SC(S)NR'R CH.sub.3 3-iodophenyl 41 SC(S)NR'R CH.sub.3 4-iodophenyl 42 SC(S)NR'R CH.sub.3 2-chloro-4-fluorophenyl 43 SC(S)NR'R CH.sub.3 2-chloro-5-fluorophenyl 44 SC(S)NR'R CH.sub.3 2-chloro-6-fluorophenyl 45 SC(S)NR'R CH.sub.3 2-chloro-4-bromophenyl 46 SC(S)NR'R CH.sub.3 2-bromo-4-chlorophenyl 47 SC(S)NR'R CH.sub.3 2-bromo-4-fluorophenyl 48 SC(S)NR'R CH.sub.3 3-bromo-4-iiuorophenyl 49 SC(S)NR'R CH.sub.3 3-chloro-4-fluorophenyl 50 SC(S)NR'R CH.sub.3 3-fluoro-4-chlorophenyl 51 SC(S)NR'R CH.sub.3 2-cyanophenyl 52 SC(S)NR'R CH.sub.3 3-cyanophenyl 53 SC(S)NR'R CH.sub.3 4-cyanophenyl 54 SC(S)NR'R CH.sub.3 2-nitrophenyl 55 SC(S)NR'R CH.sub.3 3-nitrophenyl 56 SC(S)NR'R CH.sub.3 4-nitrophenyl 57 SC(S)NR'R CH.sub.3 2-methylphenyl 2.17; 3.69; 3.76; 3.95; (4 .times. 3H); 4.33 (2H); 7.06-7.50 (8H) 58 SC(S)NR'R CH.sub.3 3-methylphenyl 2.36; 3.74; 3.77; 3.96; (4 .times. 3H); 4.32 (2H); 6.98-7.48 (8H) 59 SC(S)NR'R CH.sub.3 4-methylphenyl 2.35; 3.72; 3.77; 3.97; (4 .times. 3H); 4.30 (2H); 7.07-7.47 (8H) 60 SC(S)NR'R CH.sub.3 2,4-dimethylphenyl 61 SC(S)NR'R CH.sub.3 2,6-dimethylphenyl 62 SC(S)NR'R CH.sub.3 3,4-dimethylphenyl 63 SC(S)NR'R CH.sub.3 3,5-dimethylphenyl 64 SC(S)NR'R CH.sub.3 2,3,4-trimethylphenyl 65 SC(S)NR'R CH.sub.3 2,3,5-trimethylphenyl 66 SC(S)NR'R CH.sub.3 2,3,6-trimethylphenyl 67 SC(S)NR'R CH.sub.3 2,4,5-trimethylphenyl 68 SC(S)NR'R CH.sub.3 2,4,6-trimethylphenyl 69 SC(S)NR'R CH.sub.3 3,4,5-trimethylphenyl 70 SC(S)NR'R CH.sub.3 pentamethylphenyl 71 SC(S)NR'R CH.sub.3 2-ethylphenyl 72 SC(S)NR'R CH.sub.3 3-ethylphenyl 73 SC(S)NR'R CH.sub.3 4-ethylphenyl 74 SC(S)NR'R CH.sub.3 3,5-diethylphenyl 75 SC(S)NR'R CH.sub.3 2-n-propylphenyl 76 SC(S)NR'R CH.sub.3 3-n-propylphenyl 77 SC(S)NR'R CH.sub.3 4-n-propylphenyl 78 SC(S)NR'R CH.sub.3 2-isopropylphenyl 79 SC(S)NR'R CH.sub.3 3-isopropylphenyl 80 SC(S)NR'R CH.sub.3 4-isopropylphenyl 81 SC(S)NR'R CH.sub.3 2,4-diisopropylphenyl 82 SC(S)NR'R CH.sub.3 3,5-diisopropylphenyl 83 SC(S)NR'R CH.sub.3 4-n-butyphenyl 84 SC(S)NR'R CH.sub.3 4-sec.-butylphenyl 85 SC(S)NR'R CH.sub.3 4-isobutylphenyl 86 SC(S)NR'R CH.sub.3 4-tert.-butylphenyl 87 SC(S)NR'R CH.sub.3 3-tert.-butylphenyl 88 SC(S)NR' R CH.sub.3 2-tert.-butylphenyl 89 SC(S)NR'R CH.sub.3 2,4-di-tert.-butylphenyl 90 SC(S)NR'R CH.sub.3 3,5-di-tert.-butylphenyl 91 SC(S)NR'R CH.sub.3 4-n-hexylphenyl 92 SC(S)NR'R CH.sub.3 4-n-dodecylphenyl 93 SC(S)NR'R CH.sub.3 2-methyl-4-tert.-butylphenyl 94 SC(S)NR'R CH.sub.3 2-methyl-6-tert.-butylphenyl 95 SC(S)NR'R CH.sub.3 2-methyl-4-isopropylphenyl 96 SC(S)NR'R CH.sub.3 2-methyl-4-cyclohexylphenyl 97 SC(S)NR'R CH.sub.3 2-methyl-4-phenylphenyl 98 SC(S)NR'R CH.sub.3 2-methyl-4-benzylphenyl 99 SC(S)NR'R CH.sub.3 2-methyl-4-phenoxyphenyl100 SC(S)NR'R CH.sub.3 2-methyl-4-benzyloxyphenyl101 SC(S)NR'R CH.sub.3 2-methyl-3-chlorophenyl102 SC(S)NR'R CH.sub.3 2-methyl-4-chlorophenyl103 SC(S)NR'R CH.sub.3 2-methyl-5-chlorophenyl104 SC(S)NR'R CH.sub.3 2-methyl-6-chlorophenyl105 SC(S)NR'R CH.sub.3 2-methyl-4-fluorophenyl106 SC(S)NR'R CH.sub.3 2-methyl-3-bromophenyl107 SC(S)NR'R CH.sub.3 2-methyl-4-bromophenyl108 SC(S)NR'R CH.sub.3 2-methyl-3-methoxyphenyl109 SC(S)NR'R CH.sub.3 2-methyl-4-methoxyphenyl110 SC(S)NR'R CH.sub.3 2-methyl-5-methoxyphenyl111 SC(S)NR'R CH.sub.3 2-methyl-6-methoxyphenyl112 SC(S)NR'R CH.sub.3 2-methyl-4-isopropoxyphenyl113 SC(S)NR'R CH.sub.3 2-methyl-2,5-dimethoxyphenyl114 SC(S)NR'R CH.sub.3 2-methoxyphenyl115 SC(S)NR'R CH.sub.3 3-methoxyphenyl116 SC(S)NR'R CH.sub.3 4-methoxyphenyl117 SC(S)NR'R CH.sub.3 2,3-dimethoxyphenyl118 SC(S)NR'R CH.sub.3 2,4-dimethoxyphenyl119 SC(S)NR'R CH.sub.3 2,5-dimethoxyphenyl120 SC(S)NR'R CH.sub.3 2,6-dimethoxyphenyl121 SC(S)NR'R CH.sub.3 3,4-dimethoxyphenyl122 SC(S)NR'R CH.sub.3 3,5-dimethoxyphenyl123 SC(S)NR'R CH.sub.3 3,6-dimethoxyphenyl124 SC(S)NR'R CH.sub.3 2,3,4-trimethoxyphenyl125 SC(S)NR'R CH.sub.3 2,3,5-trimethoxyphenyl126 SC(S)NR'R CH.sub.3 2,3,6-trimethoxyphenyl127 SC(S)NR'R CH.sub.3 2,4,5-trichlorophenyl128 SC(S)NR'R CH.sub.3 2,4,6-trichloroyphenyl129 SC(S)NR'R CH.sub.3 2,3,4,6-tetrachlorophenyl130 SC(S)NR'R CH.sub.3 2,3,5,6-tetrachlorophenyl131 SC(S)NR'R CH.sub.3 2-bromophenyl132 SC(S)NR'R CH.sub.3 3-bromophenyl133 SC(S)NR'R CH.sub.3 4-bromophenyl134 SC(S)NR'R CH.sub.3 2,4-dibromophenyl135 SC(S)NR'R CH.sub.3 3-bromo-4-fluorophenyl136 SC(S)NR'R CH.sub.3 3-bromo-4-methoxyphenyl137 SC(S)NR'R CH.sub.3 2-iodophenyl138 SC(S)NR'R CH.sub.3 3-iodophenyl139 SC(S)NR'R CH.sub.3 4-iodophenyl140 SC(S)NR'R CH.sub.3 2-chloro-4-fluorophenyl141 SC(S)NR'R CH.sub.3 2-chloro-5-fluorophenyl142 SC(S)NR'R CH.sub.3 2-chloro-6-fluorophenyl143 SC(S)NR'R CH.sub.3 2-chloro-4-bromophenyl144 SC(S)NR'R CH.sub.3 2-bromo-4-chlorophenyl145 SC(S)NR'R CH.sub.3 2-bromo-4-fluorophenyl146 SC(S)NR'R CH.sub.3 3-bromo-4-chlorophenyl147 SC(S)NR'R CH.sub.3 3-chloro-4-fluorophenyl148 SC(S)NR'R CH.sub.3 3-fluoro-4-chlorophenyl149 SC(S)NR'R CH.sub.3 2-cyanophenyl150 SC(S)NR'R CH.sub.3 3-cyanophenyl151 SC(S)NR'R CH.sub.3 4-cyanophenyl152 SC(S)NR'R CH.sub.3 2-nitrophenyl153 SC(S)NR'R CH.sub.3 3-nitrophenyl154 SC(S)NR'R CH.sub.3 4-nitrophenyl155 SC(S)NR'R CH.sub.3 2-methylphenyl156 SC(S)NR'R CH.sub.3 3-methylphenyl157 SC(S)NR'R CH.sub.3 4-methylphenyl158 SC(S)NR'R CH.sub.3 2,4-dimethylphenyl159 SC(S)NR'R CH.sub.3 2,6-dimethylphenyl160 SC(S)NR'R CH.sub.3 3,4-dimethylphenyl161 SC(S)NR'R CH.sub.3 3,5-dimethylphenyl162 SC(S)NR'R CH.sub.3 2,3,4-trimethylphenyl163 SC(S)NR'R CH.sub.3 2,3,5-trimethylphenyl164 SC(S)NR'R CH.sub.3 2,3,6-trimethylphenyl165 SC(S)NR'R CH.sub.3 2,4,5-trimethylphenyl166 SC(S)NR'R CH.sub.3 2,4,6-trimethylphenyl167 SC(S)NR'R CH.sub.3 2,4,5-trimethylphenyl168 SC(S)NR'R CH.sub.3 pentamethylphenyl169 SC(S)NR'R CH.sub.3 2-ethylphenyl170 SC(S)NR'R CH.sub.3 3-ethylphenyl171 SC(S)NR'R CH.sub.3 4-ethylphenyl172 SC(S)NR'R CH.sub.3 3,5-diethylphenyl173 SC(S)NR'R CH.sub.3 2-n-propylphenyl174 SC(S)NR'R CH.sub.3 3-n-propylphenyl175 SC(S)NR'R CH.sub.3 4-n-propylphenyl176 SC(S)NR'R CH.sub.3 2,4,5-trimethoxyphenyl177 SC(S)NR'R CH.sub.3 2,4,6-trimethoxyphenyl178 SC(S)NR'R CH.sub.3 3,4,5-trimethoxyphenyl179 SC(S)NR'R CH.sub.3 2-ethoxyphenyl180 SC(S)NR'R CH.sub.3 3-ethoxyphenyl181 SC(S)NR'R CH.sub.3 4-ethoxyphenyl182 SC(S)NR'R CH.sub.3 2-isopropoxyphenyl183 SC(S)NR'R CH.sub.3 3-isopropoxyphenyl184 SC(S)NR'R CH.sub.3 4-isopropoxyphenyl185 SC(S)NR'R CH.sub.3 3-tert.-butoxyphenyl186 SC(S)NR'R CH.sub.3 4-tert.-butoxyphenyl187 SC(S)NR'R CH.sub.3 2-trifluoromethoxyphenyl188 SC(S)NR'R CH.sub.3 3-trifluoromethoxyphenyl189 SC(S)NR'R CH.sub.3 4-trifluoromethoxyphenyl190 SC(S)NR'R CH.sub.3 3-(1',1',2',2'-tetra- fluoro)-ethoxyphenyl191 SC(S)NR'R CH.sub.3 4-(1',1',2',2'-tetra- fluoro)-ethoxyphenyl192 SC(S)NR'R CH.sub.3 2-chloromethylphenyl193 SC(S)NR'R CH.sub.3 3-chloromethylphenyl194 SC(S)NR'R CH.sub.3 4-chloromethylphenyl195 SC(S)NR'R CH.sub.3 2-trifluoromethylphenyl196 SC(S)NR'R CH.sub.3 3-trifluoromethylphenyl197 SC(S)NR'R CH.sub.3 4-trifluoromethylphenyl198 SC(S)NR'R CH.sub.3 2-(methoxyiminomethyl)-phenyl199 SC(S)NR'R CH.sub.3 3-(methoxyiminomethyl)-phenyl200 SC(S)NR'R CH.sub.3 4-(methoxyiminomethyl)-phenyl201 SC(S)NR'R CH.sub.3 2-(ethoxyiminomethyl)-phenyl202 SC(S)NR'R CH.sub.3 3-(ethoxyiminomethyl)-phenyl203 SC(S)NR'R CH.sub.3 4-(ethoxyiminomethyl)-phenyl204 SC(S)NR'R CH.sub.3 2-methyl-4-methoximinoethyl- phenyl205 SC(S)NR'R CH.sub.3 2-methyl-4-methoximinomethyl- phenyl206 SC(S)NR'R CH.sub.3 2,6-dimethyl-4-methoximino- methyl-phenyl207 SC(S)NR'R CH.sub.3 2,6-dimethyl-4-methoximino- ethyl-phenyl208 SC(S)NR'R CH.sub.3 2-phenylphenyl209 SC(S)NR'R CH.sub.3 3-phenylphenyl210 SC(S)NR'R CH.sub.3 4-phenylphenyl211 SC(S)NR'R CH.sub.3 2-phenoxyphenyl212 SC(S)NR'R CH.sub.3 3-phenoxyphenyl213 SC(S)NR'R CH.sub.3 4-phenoxyphenyl214 SC(S)NR'R CH.sub.3 2-benzyloxyphenyl215 SC(S)NR'R CH.sub.3 3-benzyloxyphenyl216 SC(S)NR'R CH.sub.3 4-benzyloxyphenyl217 SC(S)NR'R CH.sub.3 4-(imidazol-1'-yl)phenyl218 SC(S)NR'R CH.sub.3 4-(piperazin-1'-yl)phenyl219 SC(S)NR'R CH.sub.3 4-(morpholin-1'-yl)phenyl220 SC(S)NR'R CH.sub.3 4-(piperidin-1'-yl)phenyl221 SC(S)NR'R CH.sub.3 4-(pyridyl-2'-oxy)phenyl222 SC(S)NR'R CH.sub.3 2-cyclopropylphenyl223 SC(S)NR'R CH.sub.3 3-cyclopropylphenyl224 SC(S)NR'R CH.sub.3 4-cyclopropylphenyl225 SC(S)NR,R CH.sub.3 3-cyclohexylphenyl226 SC(S)NR'R CH.sub.3 4-cyclohexylphenyl227 SC(S)NR'R CH.sub.3 4-oxiranylphenyl228 SC(S)NR'R CH.sub.3 4-(1',3'-dioxan-2'-yl)-phenyl229 SC(S)NR'R CH.sub.3 4-(tetrahydropyran-2-yl- oxy)-phenyl230 SC(S)NR'R CH.sub.3 1-naphthyl231 SC(S)NR'R CH.sub.3 2-naphthyl232 SC(S)NR'R CH.sub.3 benzyl 84-90.degree. C.233 SC(S)NR'R CH.sub.3 2-methylbenzyl234 SC(S)NR'R CH.sub.3 3-methylbenzyl235 SC(S)NR'R CH.sub.3 4-methylbenzyl236 SC(S)NR'R CH.sub.3 4-tert.-butylbenzyl 1.31 (9H), 4.50 (2H) amide rotamers237 SC(S)NR'R CH.sub.3 2-chlorobenzyl238 SC(S)NR'R CH.sub.3 3-chlorobenzyl239 SC(S)NR'R CH.sub.3 4-chlorobenzyl240 SC(S)NR'R CH.sub.3 2-pyridyl241 SC(S)NR'R CH.sub.3 3-pyridyl242 SC(S)NR'R CH.sub.3 4-pyridyl243 SC(S)NR'R CH.sub.3 2,6-pyrimidinyl244 SC(S)NR' R CH.sub.3 1,5-pyrimidinyl245 SC(S)NR'R CH.sub.3 2-thienyl246 SC(S)NR'R CH.sub.3 3-thienyl247 SC(S)NR'R CH.sub.3 2-furyl248 SC(S)NR'R CH.sub.3 3-furyl249 SC(S)NR'R CH.sub.3 1-pyrrolyl250 SC(S)NR'R CH.sub.3 1-imidazolyl251 SC(S)NR'R CH.sub.3 1,2,4-triazolyl252 SC(S)NR'R CH.sub.3 1,3,4-triazolyl253 SC(S)NR'R CH.sub.3 4-thiazolyl254 SC(S)NR'R CH.sub.3 2-benzothiazolyl255 SC(S)NR'R CH.sub.3 2-pyridylmethyl256 SC(S)NR'R CH.sub.3 3-pyridylmethyl257 SC(S)NR'R CH.sub.3 4-pyridylmethyl258 SC(S)NR'R Et phenyl 1.24 (3H), 3.76, 3.94 (3H), 4.03 (2 .times. CH.sub.2)259 SC(S)NR'R Et 2-methylphenyl260 SC(S)NR'R Et 2-chlorophenyl261 SC(S)NR'R Et 4-methylphenyl 1633, 1523, 1508, 1444, 1399, 1305, 1272, 1103, 1038262 SC(S)NR'R Et 2-naphtyl 110-114.degree. C.263 SC(S)SR -- CH.sub.3264 SC(S)SR -- CH.sub.2 -phenyl265 SC(S)SR -- phenyl266 SC(S)SR -- A* 114-115.degree. C.267 SC(S)OR -- CH.sub.3 3.85, 4.04, 4.14 (3H); 4.25 (2H)268 SC(S)OR -- phenyl269 SC(S)OR -- 2-CH.sub.3 -phenyl270 SC(S)OR -- 3-CH.sub.3 -phenyl271 SC(S)OR -- 4-CH.sub.3 -phenyl272 SC(S)OR -- 2-Cl-phenyl273 SC(S)OR -- 3-Cl-phenyl274 SC(S)OR -- 4-Cl-phenyl275 SC(S)OR -- CH.sub.2 -phenyl276 SC(S)OR -- CH.sub.2 -(2-Me)-phenyl 1727, 1436, 1218, 1066, 1017277 SC(S)OR -- CH.sub.2 -(3-Me)-phenyl 1727, 1437, 1218, 1066, 1018278 SC(S)OR -- CH.sub.2 -(4-Me)-phenyl279 SC(S)OR -- CH.sub.2 -(2-Cl)-phenyl 1727, 1442, 1221, 1065, 1017280 SC(S)OR -- CH.sub.2 -(3-Cl)-phenyl 3.86, 4.04 (3H), 4.28, 5.58 (2H)281 SC(S)OR -- CH.sub.2 -(4-Cl)-phenyl282 OC(O)OR -- CH.sub.3283 OC(O)OR -- tert.-butyl284 OC(O)OR -- CH.sub.2 -phenyl285 OC(O)OR -- phenyl286 SC(S)NR'R CH.sub.3 3-Me, 4-F-phenyl 2.27; 3.71; 3.78; 3.97 (4 .times. 3H); 4.32 (2H); 7.00-7.49 (7H)287 SC(S)NR'R H 2-phenyl-eth-2-yl 102-103.degree. C.288 SC(S)NR'R Me 4-tert-butoxybenzyl 2975, 1726, 1656, 1482, 1387, 1236, 1216, 1161, 1066, 1017289 SC(S)NR'R Et 3,4-(OCH.sub.2 O)phenyl 108-113.degree. C.290 SC(S)OR -- ethyl 1727, 1437, 1321, 1218, 1066, 1047, 1017291 SC(S)OR -- isopropyl 1726, 1436, 1218, 1090, 1066, 1040, 101292 SC(S)OR -- benzyl 13.87, 4.05 (3H), 4.27, 5.63__________________________________________________________________________ (2H) ##STR20## .sup.a) IR (cm.sup.-1); .sup.1 HNMR (CDCl.sub.3 /TMS); m. p.
TABLE 3______________________________________ ##STR21##No. D R' R phys. data.sup.a)______________________________________ 1 SC(S)NR'R CH.sub.3 methyl 2 SC(S)NR'R CH.sub.3 ethyl 3 SC(S)NR'R CH.sub.3 n-propyl 4 SC(S)NR'R CH.sub.3 tert.-butyl 5 SC(S)NR'R CH.sub.3 cyclopropyl 6 SC(S)NR'R CH.sub.3 cyclohexyl 7 SC(S)NR'R CH.sub.3 methoxymethyl 8 SC(S)NR'R CH.sub.3 phenoxymethyl 9 SC(S)NR'R CH.sub.3 methylthiomethyl 10 SC(S)NR'R CH.sub.3 phenyl 11 SC(S)NR'R CH.sub.3 2-fluorophenyl 12 SC(S)NR'R CH.sub.3 3-fluorophenyl 13 SC(S)NR'R CH.sub.3 4-fluorophenyl 14 SC(S)NR'R CH.sub.3 pentafluorophenyl 15 SC(S)NR'R CH.sub.3 2-chlorophenyl 16 SC(S)NR'R CH.sub.3 3-chlorophenyl 17 SC(S)NR'R CH.sub.3 4-chlorophenyl 18 SC(S)NR'R CH.sub.3 pentachlorophenyl 19 SC(S)NR'R CH.sub.3 2,3-dichlorophenyl 20 SC(S)NR'R CH.sub.3 2,,4-dichlorophenyl 21 SC(S)NR'R CH.sub.3 2,5-dichlorophenyl 22 SC(S)NR'R CH.sub.3 2,6-dichlorophenyl 23 SC(S)NR'R CH.sub.3 3,4-dichlorophenyl 24 SC(S)NR'R CH.sub.3 3,5-dichlorophenyl 25 SC(S)NR'R CH.sub.3 2,3,4-trichlorophenyl 26 SC(S)NR'R CH.sub.3 2,3,5-trichlorophenyl 27 SC(S)NR'R CH.sub.3 2,3,6-trichlorophenyl 28 SC(S)NR'R CH.sub.3 2,4,5-trichlorophenyl 29 SC(S)NR'R CH.sub.3 2,4,6-trichlorophenyl 30 SC(S)NR'R CH.sub.3 3,4,5-trichlorophenyl 31 SC(S)NR'R CH.sub.3 2,3,4,6-tetrachlorophenyl 32 SC(S)NR'R CH.sub.3 2,3,5,6-tetrachlorophenyl 33 SC(S)NR'R CH.sub.3 2-bromophenyl 34 SC(S)NR'R CH.sub.3 3-bromophenyl 35 SC(S)NR'R CH.sub.3 4-bromophenyl 36 SC(S)NR'R CH.sub.3 2,4-dibromophenyl 37 SC(S)NR'R CH.sub.3 3-bromo-4-fluorophenyl 38 SC(S)NR'R CH.sub.3 3-bromo-4-methoxyphenyl 39 SC(S)NR'R CH.sub.3 2-iodophenyl 40 SC(S)NR'R CH.sub.3 3-iodophenyl 41 SC(S)NR'R CH.sub.3 4-iodophenyl 42 SC(S)NR'R CH.sub.3 2-chloro-4-fluorophenyl 43 SC(S)NR'R CH.sub.3 2-chloro-5-fluorophenyl 44 SC(S)NR'R CH.sub.3 2-chloro-6-fluorophenyl 45 SC(S)NR'R CH.sub.3 2-chloro-4-bromophenyl 46 SC(S)NR'R CH.sub.3 2-bromo-4-chlorophenyl 47 SC(S)NR'R CH.sub.3 2-bromo-4-fluorophenyl 48 SC(S)NR'R CH.sub.3 3-bromo-4-fluorophenyl 49 SC(S)NR'R CH.sub.3 3-chloro-4-fluorophenyl 50 SC(S)NR'R CH.sub.3 3-fluoro-4-chlorophenyl 51 SC(S)NR'R CH.sub.3 2-cyanophenyl 52 SC(S)NR'R CH.sub.3 3-cyanophenyl 53 SC(S)NR'R CH.sub.3 4-cyanophenyl 54 SC(S)NR'R CH.sub.3 2-nitrophenyl 55 SC(S)NR'R CH.sub.3 3-nitrophenyl 56 SC(S)NR'R CH.sub.3 4-nitrophenyl 57 SC(S)NR'R CH.sub.3 2-methylphenyl 58 SC(S)NR'R CH.sub.3 3-methylphenyl 59 SC(S)NR'R CH.sub.3 4-methylphenyl 60 SC(S)NR'R CH.sub.3 2,4-dimethylphenyl 61 SC(S)NR'R CH.sub.3 2,6-dimethylphenyl 62 SC(S)NR'R CH.sub.3 3,4-dimethylphenyl 63 SC(S)NR'R CH.sub.3 3,5-dimethylphenyl 64 SC(S)NR'R CH.sub.3 2,3,4-trimethylphenyl 65 SC(S)NR'R CH.sub.3 2,3,5-trimethylphenyl 66 SC(S)NR'R CH.sub.3 2,3,6-trimethylphenyl 67 SC(S)NR'R CH.sub.3 2,4,5-trimethylphenyl 68 SC(S)NR'R CH.sub.3 2,4,6-trimethylphenyl 69 SC(S)NR'R CH.sub.3 3,4,5-trimethylphenyl 70 SC(S)NR'R CH.sub.3 pentamethylphenyl 71 SC(S)NR'R CH.sub.3 2-ethylphenyl 72 SC(S)NR'R CH.sub.3 3-ethylphenyl 73 SC(S)NR'R CH.sub.3 4-ethylphenyl 74 SC(S)NR'R CH.sub.3 3,5-diethylphenyl 75 SC(S)NR'R CH.sub.3 2-n-propylphenyl 76 SC(S)NR'R CH.sub.3 3-n-propylphenyl 77 SC(S)NR'R CH.sub.3 4-n-propylphenyl 78 SC(S)NR'R CH.sub.3 2-isopropylphenyl 79 SC(S)NR'R CH.sub.3 3-isopropylphenyl 80 SC(S)NR' R CH.sub.3 4-isopropylphenyl 81 SC(S)NR'R CH.sub.3 2,4-diisopropylphenyl 82 SC(S)NR'R CH.sub.3 3,5-diisopropylphenyl 83 SC(S)NR'R CH.sub.3 4-n-butyphenyl 84 SC(S)NR'R CH.sub.3 4-sec.-butylphenyl 85 SC(S)NR'R CH.sub.3 4-iso-butylphenyl 86 SC(S)NR'R CH.sub.3 4-tert.-butylphenyl 87 SC(S)NR'R CH.sub.3 3-tert.-butylphenyl 88 SC(S)NR'R CH.sub.3 2-tert.-butylphenyl 89 SC(S)NR'R CH.sub.3 2,4-di-tert.-butylphenyl 90 SC(S)NR'R CH.sub.3 3,5-di-tert.-butylphenyl 91 SC(S)NR'R CH.sub.3 4-n-hexylphenyl 92 SC(S)NR'R CH.sub.3 4-n-dodecylphenyl 93 SC(S)NR'R CH.sub.3 2-methyl-4-tert.-butylphenyl 94 SC(S)NR'R CH.sub.3 2-methyl-6-tert.-butylphenyl 95 SC(S)NR'R CH.sub.3 2-methyl-4-isopropylphenyl 96 SC(S)NR'R CH.sub.3 2-methyl-4-cyclohexylphenyl 97 SC(S)NR'R CH.sub.3 2-methyl-4-phenylphenyl 98 SC(S)NR'R CH.sub.3 2-methyl-4-benzylphenyl 99 SC(S)NR'R CH.sub.3 2-methyl-4-phenoxyphenyl100 SC(S)NR'R CH.sub.3 2-methyl-4-benzyloxyphenyl101 SC(S)NR'R CH.sub.3 2-methyl-3-chlorophenyl102 SC(S)NR'R CH.sub.3 2-methyl-4-chlorophenyl103 SC(S)NR'R CH.sub.3 2-methyl-5-chlorophenyl104 SC(S)NR'R CH.sub.3 2-methyl-6-chlorophenyl105 SC(S)NR'R CH.sub.3 2-methyl-4-fluorophenyl106 SC(S)NR'R CH.sub.3 2-methyl-3-bromophenyl107 SC(S)NR'R CH.sub.3 2-methyl-4-bromophenyl108 SC(S)NR'R CH.sub.3 2-methyl-3-methoxyphenyl109 SC(S)NR'R CH.sub.3 2-methyl-4-methoxyphenyl110 SC(S)NR'R CH.sub.3 2-methyl-5-methoxyphenyl111 SC(S)NR'R CH.sub.3 2-methyl-6-methoxyphenyl112 SC(S)NR'R CH.sub.3 2-methyl-4-isopropoxyphenyl113 SC(S)NR'R CH.sub.3 2-methyl-2,5-dimethoxyphenyl114 SC(S)NR'R CH.sub.3 2-methoxyphenyl115 SC(S)NR'R CH.sub.3 3-methoxyphenyl116 SC(S)NR'R CH.sub.3 4-methoxyphenyl117 SC(S)NR'R CH.sub.3 2,3-dimethoxyphenyl118 SC(S)NR'R CH.sub.3 2,4-dimethoxyphenyl119 SC(S)NR'R CH.sub.3 2,5-dimethoxyphenyl120 SC(S)NR'R CH.sub.3 2,6-dimethoxyphenyl121 SC(S)NR'R CH.sub.3 3,4-dimethoxyphenyl122 SC(S)NR'R CH.sub.3 3,5-dimethoxyphenyl123 SC(S)NR'R CH.sub.3 3,6-dimethoxyphenyl124 SC(S)NR'R CH.sub.3 2,3,4-trimethoxyphenyl125 SC(S)NR'R CH.sub.3 2,3,5-trimethoxyphenyl126 SC(S)NR'R CH.sub.3 2,3,6-trimethoxyphenyl127 SC(S)NR'R CH.sub.3 2,4,5-trichlorophenyl128 SC(S)NR'R CH.sub.3 2,4,6-trichloroyphenyl129 SC(S)NR'R CH.sub.3 2,3,4,6-tetrachlorophenyl130 SC(S)NR'R CH.sub.3 2,3,5,6-tetrachlorophenyl131 SC(S)NR'R CH.sub.3 2-bromophenyl132 SC(S)NR'R CH.sub.3 3-bromophenyl133 SC(S)NR'R CH.sub.3 4-bromophenyl134 SC(S)NR'R CH.sub.3 2,4-dibromophenyl135 SC(S)NR'R CH.sub.3 3-bromo-4-fluorophenyl136 SC(S)NR'R CH.sub.3 3-bromo-4-methoxyphenyl137 SC(S)NR'R CH.sub.3 2-iodophenyl138 SC(S)NR'R CH.sub.3 3-iodophenyl139 SC(S)NR'R CH.sub.3 4-iodophenyl140 SC(S)NR'R CH.sub.3 2-chloro-4-fluorophenyl141 SC(S)NR'R CH.sub.3 2-chloro-5-fluorophenyl142 SC(S)NR'R CH.sub.3 2-chloro-6-fluorophenyl143 SC(S)NR'R CH.sub.3 2-chloro-4-bromophenyl144 SC(S)NR'R CH.sub.3 2-bromo-4-chlorophenyl145 SC(S)NR'R CH.sub.3 2-bromo-4-fluorophenyl146 SC(S)NR'R CH.sub.3 3-bromo-4-chlorophenyl147 SC(S)NR'R CH.sub.3 3-chloro-4-fluorophenyl148 SC(S)NR'R CH.sub.3 3-fluoro-4-chlorophenyl149 SC(S)NR'R CH.sub.3 2-cyanophenyl150 SC(S)NR'R CH.sub.3 3-cyanophenyl151 SC(S)NR'R CH.sub.3 4-cyanophenyl152 SC(S)NR'R CH.sub.3 2-nitrophenyl153 SC(S)NR'R CH.sub.3 3-nitrophenyl154 SC(S)NR'R CH.sub.3 4-nitrophenyl155 SC(S)NR'R CH.sub.3 2-methylphenyl156 SC(S)NR'R CH.sub.3 3-methylphenyl157 SC(S)NR'R CH.sub.3 4-methylphenyl158 SC(S)NR'R CH.sub.3 2,4-dimethylphenyl159 SC(S)NR'R CH.sub.3 2,6-dimethylphenyl160 SC(S)NR'R CH.sub.3 3,4-dimethylphenyl161 SC(S)NR'R CH.sub.3 3,5-dimethylphenyl162 SC(S)NR'R CH.sub.3 2,3,4-trimethylphenyl163 SC(S)NR'R CH.sub.3 2,3,5-trimethylphenyl164 SC(S)NR'R CH.sub.3 2,3,6-trimethylphenyl165 SC(S)NR'R CH.sub.3 2,4,5-trimethylphenyl166 SC(S)NR'R CH.sub.3 2,4,6-trimethylphenyl167 SC(S)NR'R CH.sub.3 2,4,5-trimethylphenyl168 SC(S)NR'R CH.sub.3 pentamethylphenyl169 SC(S)NR'R CH.sub.3 2-ethylphenyl170 SC(S)NR'R CH.sub.3 3-ethylphenyl171 SC(S)NR'R CH.sub.3 4-ethylphenyl172 SC(S)NR'R CH.sub.3 3,5-diethylphenyl173 SC(S)NR'R CH.sub.3 2-n-propylphenyl174 SC(S)NR'R CH.sub.3 3-n-propylphenyl175 SC(S)NR'R CH.sub.3 4-n-propylphenyl176 SC(S)NR'R CH.sub.3 2,4,5-trimethoxyphenyl177 SC(S)NR'R CH.sub.3 2,4,6-trimethoxyphenyl178 SC(S)NR'R CH.sub.3 3,4,5-trimethoxyphenyl179 SC(S)NR'R CH.sub.3 2-ethoxyphenyl180 SC(S)NR'R CH.sub.3 3-ethoxyphenyl181 SC(S)NR'R CH.sub.3 4-ethoxyphenyl182 SC(S)NR'R CH.sub.3 2-isopropoxyphenyl183 SC(S)NR'R CH.sub.3 3-isopropoxyphenyl184 SC(S)NR'R CH.sub.3 4-isopropoxyphenyl185 SC(S)NR'R CH.sub.3 3-tert.-butoxyphenyl186 SC(S)NR'R CH.sub.3 4-tert.-butoxyphenyl187 SC(S)NR'R CH.sub.3 2-trifluoromethoxyphenyl188 SC(S)NR'R CH.sub.3 3-trifluoromethoxyphenyl189 SC(S)NR'R CH.sub.3 4-trifluoromethoxyphenyl190 SC(S)NR'R CH.sub.3 3-(1',1',2',2,-tetra- fluoro)-ethoxyphenyl191 SC(S)NR'R CH.sub.3 4-(1',1',2',2,-tetra- fluoro)-ethoxyphenyl192 SC(S)NR'R CH.sub.3 2-chloromethylphenyl193 SC(S)NR'R CH.sub.3 3-chloromethylphenyl194 SC(S)NR'R CH.sub.3 4-chloromethylphenyl195 SC(S)NR'R CH.sub.3 2-triiluoromethylphenyl196 SC(S)NR'R CH.sub.3 3-trifluoromethylphenyl197 SC(S)NR'R CH.sub.3 4-trifluoromethylphenyl198 SC(S)NR'R CH.sub.3 2-(methoxyiminomethyl)-phenyl199 SC(S)NR'R CH.sub.3 3-(methoxyiminomethyl)-phenyl200 SC(S)NR'R CH.sub.3 4-(methoxyiminometbyl)-phenyl201 SC(S)NR'R CH.sub.3 2-(ethoxyiminomethyl)-phenyl202 SC(S)NR'R CH.sub.3 3-(ethoxyiminomethyl)-phenyl203 SC(S)NR'R CH.sub.3 4-(ethoxyiminomethyl)-phenyl204 SC(S)NR'R CH.sub.3 2-methyl-4-methoximinoethyl- phenyl205 SC(S)NR'R CH.sub.3 2-methyl-4-methoximinomethyl- phenyl206 SC(S)NR'R CH.sub.3 2,6-dimethyl-4-methoximino- methyl-phenyl207 SC(S)NR'R CH.sub.3 2,6-dimethyl-4-methoximino- ethyl-phenyl208 SC(S)NR'R CH.sub.3 2-phenylphenyl209 SC(S)NR'R CH.sub.3 3-phenylphenyl210 SC(S)NR'R CH.sub.3 4-phenylphenyl211 SC(S)NR'R CH.sub.3 2-phenoxyphenyl212 SC(S)NR'R CH.sub.3 3-phenoxyphenyl213 SC(S)NR'R CH.sub.3 4-phenoxyphenyl214 SC(S)NR'R CH.sub.3 2-benzyloxyphenyl215 SC(S)NR'R CH.sub.3 3-benzyloxyphenyl216 SC(S)NR'R CH.sub.3 4-benzyloxyphenyl217 SC(S)NR'R CH.sub.3 4-(imidazol-1'-yl)phenyl218 SC(S)NR'R CH.sub.3 4-(piperazin-1'-yl)phenyl219 SC(S)NR'R CH.sub.3 4-(morpholin-1'-yl)phenyl220 SC(S)NR'R CH.sub.3 4-(piperidin-1'-yl)phenyl221 SC(S)NR'R CH.sub.3 4-(pyridyl-2'-oxy)phenyl222 SC(S)NR'R CH.sub.3 2-cyclopropylphenyl223 SC(S)NR'R CH.sub.3 3-cyclopropylphenyl224 SC(S)NR'R CH.sub.3 4-cyclopropylphenyl225 SC(S)NR'R CH.sub.3 3-cyclohexylphenyl226 SC(S)NR'R CH.sub.3 4-cyclohexylphenyl227 SC(S)NR'R CH.sub.3 4-oxiranylphenyl228 SC(S)NR'R CH.sub.3 4-(1',3'-dioxan-2'-yl)-phenyl229 SC(S)NR'R CH.sub.3 4-(tetrahydropyran-2-yl- oxy)-phenyl230 SC(S)NR'R CH.sub.3 1-naphthyl231 SC(S)NR'R CH.sub.3 2-naphthyl232 SC(S)NR'R CH.sub.3 benzyl233 SC(S)NR'R CH.sub.3 2-methylbenzyl234 SC(S)NR'R CH.sub.3 3-methylbenzyl235 SC(S)NR'R CH.sub. 3 4-methylbenzyl236 SC(S)NR'R CH.sub.3 4-tert.-butylbenzyl237 SC(S)NR'R CH.sub.3 2-chlorobenzyl238 SC(S)NR'R CH.sub.3 3-chlorobenzyl239 SC(S)NR'R CH.sub.3 4-chlorobenzyl240 SC(S)NR'R CH.sub.3 2-pyridyl241 SC(S)NR'R CH.sub.3 3-pyridyl242 SC(S)NR'R CH.sub.3 4-pyridyl243 SC(S)NR'R CH.sub.3 2,6-pyrimidinyl244 SC(S)NR'R CH.sub.3 1,5-pyrimidinyl245 SC(S)NR'R CH.sub.3 2-thienyl246 SC(S)NR'R CH.sub.3 3-thienyl247 SC(S)NR'R CH.sub.3 2-furyl248 SC(S)NR'R CH.sub.3 3-furyl249 SC(S)NR'R CH.sub.3 1-pyrrolyl250 SC(S)NR'R CH.sub.3 1-imidazolyl251 SC(S)NR'R CH.sub.3 1,2,4-triazolyl252 SC(S)NR'R CH.sub.3 1,3,4-triazolyl253 SC(S)NR'R CH.sub.3 4-thiazolyl254 SC(S)NR'R CH.sub.3 2-benzothiazolyl255 SC(S)NR'R CH.sub.3 2-pyridylmethyl256 SC(S)NR'R CH.sub.3 3-pyridylmethyl257 SC(S)NR'R CH.sub.3 4-pyridylmethyl258 SC(S)NR'R Et phenyl259 SC(S)NR'R Et 2-methylphenyl260 SC(S)NR'R Et 2-chlorophenyl261 SC(S)NR'R Et 4-methylphenyl262 SC(S)NR'R Et 2-naphtyl263 SC(S)SR -- CH.sub.3264 SC(S)SR -- CH.sub.2 -phenyl265 SC(S)SR -- phenyl266 SC(S)SR -- A*267 SC(S)OR -- CH.sub.3268 SC(S)OR -- phenyl269 SC(S)OR -- 2-CH.sub.3 -phenyl270 SC(S)OR -- 3-CH.sub.3 -phenyl271 SC(S)OR -- 4-CH.sub.3 -phenyl272 SC(S)OR -- 2-Cl-phenyl273 SC(S)OR -- 3-Cl-phenyl274 SC(S)OR -- 4-Cl-phenyl275 SC(S)OR -- CH.sub.2 -phenyl276 SC(S)OR -- CH.sub.2 -(2-Me)-phenyl277 SC(S)OR -- CH.sub.2 -(3-Me)-phenyl278 SC(S)OR -- CH.sub.2 -(4-Me)-phenyl279 SC(S)OR -- CH.sub.2 -(2-Cl)-phenyl280 SC(S)OR -- CH.sub.2 -(3-Cl)phenyl281 SC(S)OR -- CH.sub.2 -(4-Cl)phenyl282 OC(O)OR -- CH.sub.3283 OC(O)OR -- tert.-butyl284 OC(O)OR -- CH.sub.2 -phenyl285 OC(O)OR -- phenyl286 SC(S)NR'R CH.sub.3 3-Me, 4-F-phenyl______________________________________ ##STR22## .sup.a) IR (cm.sup.-1); .sup.1 HNMR (CDCl.sub.3 /TMS); m. p.
TABLE 4__________________________________________________________________________ ##STR23##No. D R' R phys. data.sup.a)__________________________________________________________________________ 1 SC(S)NR'R CH.sub.3 methyl 2 SC(S)NR'R CH.sub.3 ethyl 3 SC(S)NR'R CH.sub.3 n-propyl 4 SC(S)NR'R CH.sub.3 tert.-butyl 5 SC(S)NR'R CH.sub.3 cyclopropyl 6 SC(S)NR'R CH.sub.3 cyclohexyl 7 SC(S)NR'R CH.sub.3 methoxymethyl 8 SC(S)NR'R CH.sub.3 phenoxymethyl 9 SC(S)NR'R CH.sub.3 methylthiomethyl 10 SC(S)NR'R CH.sub.3 phenyl 11 SC(S)NR'R CH.sub.3 2-fluorophenyl 12 SC(S)NR'R CH.sub.3 3-fluorophenyl 13 SC(S)NR'R CH.sub.3 4-fluorophenyl 152-156.degree. C. 14 SC(S)NR'R CH.sub.3 pentafluorophenyl 15 SC(S)NR'R CH.sub.3 2-chlorophenyl 16 SC(S)NR'R CH.sub.3 3-chlorophenyl 2.90(d, 3H), 3.71, 3.89(2 .times. 3H), 4.35 (2H), 6.72(1H), 7.10-7.46(8H) 17 SC(S)NR'R CH.sub.3 4-chlorophenyl 18 SC(S)NR'R CH.sub. 3 pentachlorophenyl 19 SC(S)NR'R CH.sub.3 2,3-dichlorophenyl 20 SC(S)NR'R CH.sub.3 2,,4-dichlorophenyl 21 SC(S)NR'R CH.sub.3 2,5-dichlorophenyl 22 SC(S)NR'R CH.sub.3 2,6-dichlorophenyl 23 SC(S)NR'R CH.sub.3 3,4-dichlorophenyl 24 SC(S)NR'R CH.sub.3 3,5-dichlorophenyl 25 SC(S)NR'R CH.sub.3 2,3,4-trichlorophenyl 26 SC(S)NR'R CH.sub.3 2,3,5-trichlorophenyl 27 SC(S)NR'R CH.sub.3 2,3,6-trichlorophenyl 28 SC(S)NR'R CH.sub.3 2,4,5-trichlorophenyl 29 SC(S)NR'R CH.sub.3 2,4,6-trichlorophenyl 30 SC(S)NR'R CH.sub.3 3,4,5-trichlorophenyl 31 SC(S)NR'R CH.sub.3 2,3,4,6-tetrachlorophenyl 32 SC(S)NR'R CH.sub.3 2,3,5,6-tetrachlorophenyl 33 SC(S)NR'R CH.sub.3 2-bromophenyl 34 SC(S)NR'R CH.sub.3 3-bromophenyl 35 SC(S)NR'R CH.sub.3 4-bromophenyl 36 SC(S)NR'R CH.sub.3 2,4-dibromophenyl 37 SC(S)NR'R CH.sub.3 3-bromo-4-fluorophenyl 38 SC(S)NR'R CH.sub.3 3-bromo-4-methoxyphenyl 39 SC(S)NR'R CH.sub.3 2-iodophenyl 40 SC(S)NR'R CH.sub.3 3-iodophenyl 41 SC(S)NR'R CH.sub.3 4-iodophenyl 42 SC(S)NR'R CH.sub.3 2-chloro-4-fluorophenyl 43 SC(S)NR'R CH.sub.3 2-chloro-5-fluorophenyl 44 SC(S)NR'R CH.sub.3 2-chloro-6-fluorophenyl 45 SC(S)NR'R CH.sub.3 2-chloro-4-bromophenyl 46 SC(S)NR'R CH.sub.3 2-bromo-4-chlorophenyl 47 SC(S)NR'R CH.sub.3 2-bromo-4-fluorophenyl 48 SC(S)NR'R CH.sub.3 3-bromo-4-fluorophenyl 49 SC(S)NR'R CH.sub.3 3-chloro-4-fluorophenyl 50 SC(S)NR'R CH.sub.3 3-fluoro-4-chlorophenyl 51 SC(S)NR'R CH.sub.3 2-cyanophenyl 52 SC(S)NR'R CH.sub.3 3-cyanophenyl 53 SC(S)NR'R CH.sub.3 4-cyanophenyl 54 SC(S)NR'R CH.sub.3 2-nitrophenyl 55 SC(S)NR'R CH.sub.3 3-nitrophenyl 56 SC(S)NR'R CH.sub.3 4-nitrophenyl 57 SC(S)NR'R CH.sub.3 2-methylphenyl 58 SC(S)NR'R CH.sub.3 3-methylphenyl 2.36; 3.74; 3.88(3 .times. 3H); 2.90(d, 3H); 4.34(2H); 6.69(1H); 7.02-7.47(8H) 59 SC(S)NR'R CH.sub.3 4-methylphenyl 2.35; 3.72; 3.88(3 .times. 3H); 2.89(d, 3H); 4.32(2H); 6.67(1H); 7.05-7.43(8H) 60 SC(S)NR'R CH.sub.3 2,4-dimethylphenyl 61 SC(S)NR'R CH.sub.3 2,6-dimethylphenyl 62 SC(S)NR'R CH.sub.3 3,4-dimethylphenyl 63 SC(S)NR'R CH.sub.3 3,5-dimethylphenyl 64 SC(S)NR'R CH.sub.3 2,3,4-trimethylphenyl 65 SC(S)NR'R CH.sub.3 2,3,5-trimethylphenyl 66 SC(S)NR'R CH.sub.3 2,3,6-trimethylphenyl 67 SC(S)NR'R CH.sub.3 2,4,5-trimethylphenyl 68 SC(S)NR'R CH.sub.3 2,4,6-trimethylphenyl 69 SC(S)NR'R CH.sub.3 3,4,5-trimethylphenyl 70 SC(S)NR'R CH.sub.3 pentamethylphenyl 71 SC(S)NR'R CH.sub.3 2-ethylphenyl 72 SC(S)NR'R CH.sub.3 3-ethylphenyl 73 SC(S)NR'R CH.sub.3 4-ethylphenyl 74 SC(S)NR'R CH.sub.3 3,5-diethylphenyl 75 SC(S)NR'R CH.sub.3 2-n-propylphenyl 76 SC(S)NR'R CH.sub.3 3-n-propylphenyl 77 SC(S)NR'R CH.sub.3 4-n-propylphenyl 78 SC(S)NR'R CH.sub.3 2-isopropylphenyl 79 SC(S)NR'R CH.sub.3 3-isopropylphenyl 80 SC(S)NR'R CH.sub.3 4-isopropylphenyl 81 SC(S)NR'R CH.sub.3 2,4-diisopropylphenyl 82 SC(S)NR'R CH.sub.3 3,5-diisopropylphenyl 83 SC(S)NR'R CH.sub.3 4-n-butyphenyl 84 SC(S)NR'R CH.sub.3 4-sec.-butylphenyl 85 SC(S)NR'R CH.sub.3 4-iso-butylphenyl 86 SC(S)NR'R CH.sub.3 4-tert.-butylphenyl 87 SC(S)NR'R CH.sub.3 3-tert.-butylphenyl 88 SC(S)NR'R CH.sub.3 2-tert.-butylphenyl 89 SC(S)NR'R CH.sub.3 2,4-di-tert.-butylphenyl 90 SC(S)NR'R CH.sub.3 3,5-di-tert.-butylphenyl 91 SC(S)NR'R CH.sub.3 4-n-hexylphenyl 92 SC(S)NR'R CH.sub.3 4-n-dodecylphenyl 93 SC(S)NR'R CH.sub.3 2-methyl-4-tert.-butylphenyl 94 SC(S)NR'R CH.sub.3 2-methyl-6-tert.-butylphenyl 95 SC(S)NR'R CH.sub.3 2-methyl-4-isopropylphenyl 96 SC(S)NR'R CH.sub.3 2-methyl-4-cyclohexylphenyl 97 SC(S)NR'R CH.sub.3 2-methyl-4-phenylphenyl 98 SC(S)NR'R CH.sub.3 2-methyl-4-benzylphenyl 99 SC(S)NR'R CH.sub.3 2-methyl-4-phenoxyphenyl100 SC(S)NR'R CH.sub.3 2-methyl-4-benzyloxyphenyl101 SC(S)NR'R CH.sub.3 2-methyl-3-chlorophenyl102 SC(S)NR'R CH.sub.3 2-methyl-4-chlorophenyl103 SC(S)NR'R CH.sub.3 2-methyl-5-chlorophenyl104 SC(S)NR'R CH.sub.3 2-methyl-6-chlorophenyl105 SC(S)NR'R CH.sub.3 2-methyl-4-fluorophenyl106 SC(S)NR'R CH.sub.3 2-methyl-3-bromophenyl107 SC(S)NR'R CH.sub.3 2-methyl-4-bromophenyl108 SC(S)NR'R CH.sub.3 2-methyl-3-methoxyphenyl109 SC(S)NR'R CH.sub.3 2-methyl-4-methoxyphenyl110 SC(S)NR'R CH.sub.3 2-methyl-5-methoxyphenyl111 SC(S)NR'R CH.sub.3 2-methyl-6-methoxyphenyl112 SC(S)NR'R CH.sub.3 2-methyl-4-isopropoxyphenyl113 SC(S)NR'R CH.sub.3 2-methyl-2,5-dimethoxyphenyl114 SC(S)NR'R CH.sub.3 2-methoxyphenyl115 SC(S)NR'R CH.sub.3 3-methoxyphenyl116 SC(S)NR'R CH.sub.3 4-methoxyphenyl117 SC(S)NR'R CH.sub.3 2,3-dimethoxyphenyl118 SC(S)NR'R CH.sub.3 2,4-dimethoxyphenyl119 SC(S)NR'R CH.sub.3 2,5-dimethoxyphenyl120 SC(S)NR'R CH.sub.3 2,6-dimethoxyphenyl121 SC(S)NR'R CH.sub.3 3,4-dimethoxyphenyl122 SC(S)NR'R CH.sub.3 3,5-dimethoxyphenyl123 SC(S)NR'R CH.sub.3 3,6-dimethoxyphenyl124 SC(S)NR'R CH.sub.3 2,3,4-trimethoxyphenyl125 SC(S)NR'R CH.sub.3 2,3,5-trimethoxyphenyl126 SC(S)NR'R CH.sub.3 2,3,6-trimethoxyphenyl127 SC(S)NR'R CH.sub.3 2,4,5-trichlorophenyl128 SC(S)NR'R CH.sub.3 2,4,6-trichloroyphenyl129 SC(S)NR'R CH.sub.3 2,3,4,6-tetrachlorophenyl130 SC(S)NR'R CH.sub.3 2,3,5,6-tetrachlorophenyl131 SC(S)NR'R CH.sub.3 2-bromophenyl132 SC(S)NR'R CH.sub.3 3-bromophenyl133 SC(S)NR'R CH.sub.3 4-bromophenyl134 SC(S)NR'R CH.sub.3 2,4-dibromophenyl135 SC(S)NR'R CH.sub.3 3-bromo-4-fluorophenyl136 SC(S)NR'R CH.sub.3 3-bromo-4-methoxyphenyl137 SC(S)NR'R CH.sub.3 2-iodophenyl138 SC(S)NR'R CH.sub.3 3-iodophenyl139 SC(S)NR'R CH.sub.3 4-iodophenyl140 SC(S)NR'R CH.sub.3 2-chloro-4-fluorophenyl141 SC(S)NR'R CH.sub.3 2-chloro-5-fluorophenyl142 SC(S)NR'R CH.sub.3 2-chloro-6-fluorophenyl143 SC(S)NR'R CH.sub.3 2-chloro-4-bromophenyl144 SC(S)NR'R CH.sub.3 2-bromo-4-chlorophenyl145 SC(S)NR'R CH.sub.3 2-bromo-4-fluorophenyl146 SC(S)NR'R CH.sub.3 3-bromo-4-chlorophenyl147 SC(S)NR'R CH.sub.3 3-chloro-4-fluorophenyl148 SC(S)NR'R CH.sub.3 3-fluoro-4-chlorophenyl149 SC(S)NR'R CH.sub.3 2-cyanophenyl150 SC(S)NR'R CH.sub.3 3-cyanophenyl151 SC(S)NR'R CH.sub.3 4-cyanophenyl152 SC(S)NR'R CH.sub.3 2-nitrophenyl153 SC(S)NR'R CH.sub.3 3-nitrophenyl154 SC(S)NR'R CH.sub.3 4-nitrophenyl155 SC(S)NR'R CH.sub.3 2-methylphenyl156 SC(S)NR'R CH.sub.3 3-methylphenyl157 SC(S)NR'R CH.sub.3 4-methylphenyl158 SC(S)NR'R CH.sub.3 2,4-dimethylphenyl159 SC(S)NR'R CH.sub.3 2,6-dimethylphenyl160 SC(S)NR'R CH.sub.3 3,4-dimethylphenyl161 SC(S)NR'R CH.sub.3 3,5-dimethylphenyl162 SC(S)NR'R CH.sub.3 2,3,4-trimethylphenyl163 SC(S)NR'R CH.sub.3 2,3,5-trimethylphenyl164 SC(S)NR'R CH.sub.3 2,3,6-trimethylphenyl165 SC(S)NR'R CH.sub.3 2,4,5-trimethylphenyl166 SC(S)NR'R CH.sub.3 2,4,6-trimethylphenyl167 SC(S)NR'R CH.sub.3 2,4,5-trimethylphenyl168 SC(S)NR'R CH.sub.3 pentamethylphenyl169 SC(S)NR'R CH.sub.3 2-ethylphenyl170 SC(S)NR'R CH.sub.3 3-ethylphenyl171 SC(S)NR'R CH.sub.3 4-ethylphenyl172 SC(S)NR'R CH.sub.3 3,5-diethylphenyl173 SC(S)NR'R CH.sub.3 2-n-propylphenyl174 SC(S)NR'R CH.sub.3 3-n-propylphenyl175 SC(S)NR'R CH.sub.3 4-n-propylphenyl176 SC(S)NR'R CH.sub.3 2,4,5-trimethoxyphenyl177 SC(S)NR'R CH.sub.3 2,4,6-trimethoxyphenyl178 SC(S)NR'R CH.sub.3 3,4,5-trimethoxyphenyl179 SC(S)NR'R CH.sub.3 2-ethoxyphenyl180 SC(S)NR'R CH.sub.3 3-ethoxyphenyl181 SC(S)NR'R CH.sub.3 4-ethoxyphenyl182 SC(S)NR'R CH.sub.3 2-isopropoxyphenyl183 SC(S)NR'R CH.sub.3 3-isopropoxyphenyl184 SC(S)NR'R CH.sub.3 4-isopropoxyphenyl185 SC(S)NR'R CH.sub.3 3-tert.-butoxyphenyl186 SC(S)NR'R CH.sub.3 4-tert.-butoxyphenyl187 SC(S)NR'R CH.sub.3 2-trifluoromethoxyphenyl188 SC(S)NR'R CH.sub.3 3-trifluoromethoxyphenyl189 SC(S)NR'R CH.sub.3 4-trifluoromethoxyphenyl190 SC(S)NR'R CH.sub.3 3-(1',1',2',2'-tetra-fluoro)-ethoxyphenyl191 SC(S)NR'R CH.sub.3 4-(1',1',2',2'-tetra-fluoro)-ethoxyphenyl192 SC(S)NR'R CH.sub.3 2-chloromethylphenyl193 SC(S)NR'R CH.sub.3 3-chloromethylphenyl194 SC(S)NR'R CH.sub.3 4-chloromethylphenyl195 SC(S)NR'R CH.sub.3 2-trifluoromethylphenyl196 SC(S)NR'R CH.sub.3 3-trifluoromethylphenyl197 SC(S)NR'R CH.sub.3 4-trifluoromethylphenyl198 SC(S)NR'R CH.sub.3 2-(methoxyiminomethyl)-phenyl199 SC(S)NR'R CH.sub.3 3-(metboxyiminomethyl)-phenyl200 SC(S)NR'R CH.sub.3 4-(methoxyiminomethyl)-phenyl201 SC(S)NR'R CH.sub.3 2-(ethoxyiminomethyl)-phenyl202 SC(S)NR'R CH.sub.3 3-(ethoxyiminomethyl)-phenyl203 SC(S)NR'R CH.sub.3 4-(ethoxyiminomethyl)-phenyl204 SC(S)NR'R CH.sub.3 2-methyl-4-methoximinoethyl-phenyl205 SC(S)NR'R CH.sub.3 2-methyl-4-methoximinomethyl-phenyl206 SC(S)NR'R CH.sub.3 2,6-dimethyl-4-methoximinomethyl-phenyl207 SC(S)NR'R CH.sub.3 2,6-dimethyl-4-methoximinoethyl-phenyl208 SC(S)NR'R CH.sub.3 2-phenylphenyl209 SC(S)NR'R CH.sub.3 3-phenylphenyl210 SC(S)NR'R CH.sub.3 4-phenylphenyl211 SC(S)NR'R CH.sub.3 2-phenoxyphenyl212 SC(S)NR'R CH.sub.3 3-phenoxyphenyl213 SC(S)NR'R CH.sub.3 4-phenoxyphenyl214 SC(S)NR'R CH.sub.3 2-benzyloxyphenyl215 SC(S)NR'R CH.sub.3 3-benzyloxyphenyl216 SC(S)NR'R CH.sub.3 4-benzyloxyphenyl217 SC(S)NR'R CH.sub.3 4-(imidazol-1'-yl)phenyl218 SC(S)NR'R CH.sub.3 4-(piperazin-1'-yl)phenyl219 SC(S)NR'R CH.sub.3 4-(morpholin-1'-yl)phenyl220 SC(S)NR'R CH.sub.3 4-(piperidin-1'-yl)phenyl221 SC(S)NR'R CH.sub.3 4-(pyridyl-2'-oxy)phenyl222 SC(S)NR'R CH.sub.3 2-cyclopropylphenyl223 SC(S)NR'R CH.sub.3 3-cyclopropylphenyl224 SC(S)NR'R CH.sub.3 4-cyclopropylphenyl225 SC(S)NR'R CH.sub.3 3-cyclohexylphenyl226 SC(S)NR'R CH.sub.3 4-cyclohexylphenyl227 SC(S)NR'R CH.sub.3 4-oxiranylphenyl228 SC(S)NR'R CH.sub.3 4-(1',3'-dioxan-2'-yl)-phenyl229 SC(S)NR'R CH.sub.3 4-(tetrahydropyran-2-yl-oxy)-phenyl230 SC(S)NR'R CH.sub.3 1-naphthyl231 SC(S)NR'R CH.sub.3 2-naphthyl232 SC(S)NR'R CH.sub.3 benzyl233 SC(S)NR'R CH.sub.3 2-methylbenzyl234 SC(S)NR'R CH.sub.3 3-methylbenzyl235 SC(S)NR'R CH.sub.3 4-methylbenzyl236 SC(S)NR'R CH.sub.3 4-tert.-butylbenzyl237 SC(S)NR'R CH.sub.3 2-chlorobenzyl238 SC(S)NR'R CH.sub.3 3-chlorobenzyl239 SC(S)NR'R CH.sub.3 4-chlorobenzyl240 SC(S)NR'R CH.sub.3 2-pyridyl241 SC(S)NR'R CH.sub.3 3-pyridyl242 SC(S)NR'R CH.sub.3 4-pyridyl243 SC(S)NR'R CH.sub.3 2,6-pyrimidinyl244 SC(S)NR'R CH.sub.3 1,5-pyrimidinyl245 SC(S)NR'R CH.sub.3 2-thienyl246 SC(S)NR'R CH.sub.3 3-thienyl247 SC(S)NR'R CH.sub.3 2-furyl248 SC(S)NR'R CH.sub.3 3-furyl249 SC(S)NR'R CH.sub.3 1-pyrrolyl250 SC(S)NR'R CH.sub.3 1-imidazolyl251 SC(S)NR'R CH.sub.3 1,2,4-triazolyl252 SC(S)NR'R CH.sub.3 1,3,4-triazolyl253 SC(S)NR'R CH.sub.3 4-thiazolyl254 SC(S)NR'R CH.sub.3 2-benzothiazolyl255 SC(S)NR'R CH.sub.3 2-pyridylmethyl256 SC(S)NR'R CH.sub.3 3-pyridylmethyl257 SC(S)NR'R CH.sub.3 4-pyridylmethyl258 SC(S)NR'R Et phenyl 162.degree. C.259 SC(S)NR'R Et 2-methylphenyl260 SC(S)NR'R Et 2-chlorophenyl261 SC(S)NR'R Et 4-methylphenyl 1663, 1523, 1508, 1444, 1399, 1385, 1272, 1103, 1038262 SC(S)NR'R Et 2-naphthyl263 SC(S)SR -- CH.sub.3264 SC(S)SR -- CH.sub.2 -phenyl265 SC(S)SR -- phenyl266 SC(S)SR -- A*267 SC(S)OR -- CH.sub.3268 SC(S)OR -- phenyl269 SC(S)OR -- 2-CH.sub.3 -phenyl270 SC(S)OR -- 3-CH.sub.3 -phenyl271 SC(S)OR -- 4-CH.sub.3 -phenyl272 SC(S)OR -- 2-Cl-phenyl273 SC(S)OR -- 3-Cl-phenyl274 SC(S)OR -- 4-Cl-phenyl275 SC(S)OR -- CH.sub.2 -phenyl276 SC(S)OR -- CH.sub.2 -(2-Me)-phenyl277 SC(S)OR -- CH.sub.2 -(3-Me)-phenyl278 SC(S)OR -- CH.sub.2 -(4-Me)-phenyl279 SC(S)OR -- CH.sub.2 -(2-Cl)-phenyl280 SC(S)OR -- CH.sub.2 -(3-Cl)phenyl281 SC(S)OR -- CH.sub.2 -(4-Cl)phenyl282 OC(O)OR -- CH.sub.3283 OC(O)OR -- tert.-butyl284 OC(O)OR -- CH.sub.2 -phenyl285 OC(O)OR -- phenyl 5.13 ppm (CH.sub.2)286 SC(S)NR'R CH.sub.3 3-Me, 4-F-phenyl 2.29; 3.73; 3.90(3 .times. 3H), 2.92(d, 3H), 4.35 2H), 6.70(1H), 6.98-7.46(7H)287 OC(O)NR'R H i-propyl 138-140.degree. C.288 OC(O)NR'R H tert.-butyl 143-145.degree. C.289 OC(O)NR'R H C(Me).sub. 2 C CH 117-119.degree. C.290 OC(O)NR'R H 2-Me-phenyl 140-141.degree. C.291 OC(O)NR'R H 3-Me-phenyl 150-152.degree. C.292 OC(O)NR'R H 4-Me-phenyl 204-205.degree. C.293 OC(O)NR'R H 4-F-phenyl 136-139.degree. C.294 OC(O)NR'R H 2,6-Cl.sub.2 -phenyl 195-198.degree. C.295 OC(O)NR'R H 3,5-Cl.sub.2 -phenyl 162-164.degree. C.__________________________________________________________________________ ##STR24## .sup.a) IR (cm.sup.-1); .sup.1 HNMR (CDCl.sub.3 /TMS); m. p.
The novel compounds are suitable as fungicides.
The fungicidal compounds, or agents containing them, may be applied for instance in the form of directly sprayable solutions, powders, suspensions (including high-percentage aqueous, oily or other suspensions), dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are being used, but they must ensure as fine a distribution of the active ingredients according to the invention as possible.
Normally, the plants are sprayed or dusted with the active ingredients or the seeds of the plants are treated with the active ingredients.
The formulations are produced in known manner, for example by extending the active ingredient with solvents and/or carriers, with or without the use of emulsifiers and dispersants; if water is used as solvent, it is also possible to employ other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are solvents such as aromatics (e.g., xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g., crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylformamide), and water; carriers such as ground natural minerals (e.g., kaolins, aluminas, talc and chalk) and ground synthetic minerals (e.g., highly disperse silica and silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates); and dispersants such as lignin-sulfite waste liquors and methylcellulose.
Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, e.g., ligninsulfonic acid, phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylaryl sulfonates, and alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methyl cellulose.
Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.
Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain meals, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.
Examples of such formulations are given below.
I. A solution of 90 parts by weight of compound no. 16 from Table 4 and 10 parts by weight of N-methyl-.alpha.-pyrrolidone, which is suitable for application in the form of very fine drops.
II. A mixture of 20 parts by weight of compound no. 58 from Table 4, 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely dispersing the mixture in water, an aqueous dispersion is obtained.
III. An aqueous dispersion of 20 parts by weight of compound no. 59 from Table 4, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil.
IV. An aqueous dispersion of 20 parts by weight of compound no. 157 from Table 4, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210.degree. and 280.degree. C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil.
V. A hammer-milled mixture of 80 parts by weight of compound no. 286 from Table 4, 3 parts by weight of the sodium salt of diisobutylnaphthalene-.alpha.-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel. By finely dispersing the mixture in 20,000 parts by weight of water, a spray liquor is obtained.
VI. An intimate mixture of 3 parts by weight of compound no. 16 from Table 4 and 97 parts by weight of particulate kaolin. The dust contains 3wt % of the active ingredient.
VII. An intimate mixture of 30 parts by weight of compound no. 58 from Table 4, 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil sprayed onto the surface of this silica gel. This formulation of the active ingredient exhibits good adherence.
VIII. A stable aqueous dispersion of 40 parts by weight of compound no. 59 from Table 4, 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water, which dispersion can be further diluted.
IX. A stable oily dispersion of 20 parts by weight of compound no. 157 from Table 4, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid-ureaformaldehyde condensate and 68 parts by weight of a paraffinic mineral oil.
The novel compounds are extremely effective on a broad spectrum of phytopathogenic fungi, in particular those from the class consisting of the Ascomycetes and Basidiomycetes. Some of them have a remarkably high systemic mobility and action after application to the soil and particularly to foliage.
The fungicidal compounds are of particular interest for controlling a large number of fungi in various crops or their seeds, especially wheat, rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee, sugar cane, fruit and ornamentals in horticulture and viticulture, and in vegetables such as cucumbers, beans and cucurbits.
The compounds are applied by treating the seeds, plants, materials or soil to be protected against fungus attack with a fungicidally effective amount of the active ingredients.
The compounds may be applied before or after infection of the materials, plants or seeds by the fungi.
The compounds I are particularly useful for controlling the following plant diseases:
Erysiphe graminis in cereals,
Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,
Podosphaera leucotricha in apples,
Uncinula necator in vines,
Puccinia species in cereals,
Rhizoctonia solani in cotton,
Ustilago species in cereals and sugar cane,
Venturia inaequalis (scab) in apples,
Helminthosporium species in cereals,
Septoria nodorum in wheat,
Botrytis cinerea (gray mold) in strawberries and grapes,
Cercospora arachidicola in groundnuts,
Pseudocercosporella herpotrichoides in wheat and barley,
Pyricularia oryzae in rice,
Phytophthora infestans in potatoes and tomatoes,
Fusarium and Verticillium species in various plants,
Plasmopara viticola in grapes,
Alternaria species in fruit and vegetables.
The novel compounds may also be used for protecting materials (timber), for example against Paecilomyces variotii.
The fungicidal agents generally contain from 0.1 to 95, and preferably from 0.5 to 90, wt % of active ingredient.
The application rates depend on the type of effect desired, but are generally from 0.02 to 3 kg of active ingredient per hectare.
When the active ingredients are used for treating seed, application rates of from 0.001 to 50, and preferably from 0.01 to 10, g per kg of seed are generally required.
When the agents according to the invention are used as fungicides, they may be employed together with other active ingredients, e.g., herbicides, insecticides, growth regulators, other fungicides and fertilizers.
When admixed with other fungicides, the spectrum of fungicidal action is in many instances increased.
Use examples
The active ingredients used for comparison purposes were methyl .alpha.-[2-(Phenylthiomethyl)-phenyl]-.beta.-methoxyacrylate (A) and methyl 2-(phenylthiomethyl)-.alpha.-methoxyimino-phenylacetate (B).
Use Example 1
Action on wheat mildew
Leaves of pot-grown wheat seedlings of the "Fruhgold" variety were sprayed with aqueous liquors containing (dry basis) 80% of active ingredient and 20% of emulsifier, and dusted, 24 hours after the sprayed-on layer had dried, with spores of wheat mildew (Erysiphe graminis var. tritici). The plants were then set up in the greenhouse at from 20.degree. to 22.degree. C. and a relative humidity of from 75 to 80%. The extent of mildew spread was assessed after 7 days.
The results show that active ingredient no. 16 from Table 1 has, when applied as a spray liquor containing 63 ppm of active ingredient, a better fungicidal action (15% leaf attack) than prior art comparative agent A (40% leaf attack).
Use Example 2
Action on Plasmopara viticola
Leaves of potted vines of the Muller-Thurgau variety were sprayed with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% of emulsifier. To assess the duration of action, the plants were set up, after the sprayed-on layer had dried, for 8 days in the greenhouse. Then the leaves were infected with a zoospore suspension of Plasmopara viticola. The plants were first placed for 48 hours in a water vapor-saturated cheer at 24.degree. C. and then in a greenhouse for 5 days at from 20.degree. to 30.degree. C. To accelerate and intensify the sporangiophore discharge, the plants were then again placed in the moist cheer for 16 hours. The extent of fungus attack was then assessed on the undersides of the leaves.
The results show that active ingredient no. 13 from Table 2 has, when applied as a spray liquor containing 63 ppm of active ingredient, a better fungicidal action (15% leaf attack) than prior art active ingredient B (40% leaf attack).

Number	Date	Country
0378308	Jul 1990	EPX
2172595	Sep 1986	GBX
2225011	May 1990	GBX
WO9307116	Apr 1993	WOX

Benzyl derivatives and pesticides containing them

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Entry
CA 113(21):190939K Preparation . . . fungicides. Richards et al., p. 680, 1990.
CA 114(9):81863f Preparation . . . fungicides. Cliff et al., p. 741, 1991.