O-Benzyloxime ethers and crop protection agents containing these compounds

The present invention relates to novel O-benzyloxime ethers and a method for controlling pests, in particular fungi, insects, nematodes and spider mites with these compounds.
It is known that substituted phenylacetic acid oxime derivatives can be used as fungicides (European Patent 253,213). However, their action is unsatisfactory.
We have found, surprisingly, that O-benzyloxime ethers of the general formula I ##STR4## where X is CH.sub.2, 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,
Y is O, S or NR.sup.5,
R.sup.1, R.sup.2 and R.sup.5 are each H or C.sub.1 -C.sub.4 -alkyl,
Z.sup.1 and Z.sup.2 are identical or different and are each H, halogen, methyl, methoxy or cyano,
R.sup.3 and R.sup.4 are identical or different and are each hydrogen, cyano, straight-chain or branched C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl, 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, arylthio-C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.5 -haloalkenyl, C.sub.3 -C.sub.6 -cycloalkenyl, C.sub.3 -C.sub.6 -halocycloalkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, benzylthio, C.sub.1 -C.sub.4 -alkylcarbonyl, unsubstituted or substituted phenylcarbonyl, unsubstituted or substituted benzylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, unsubstituted or substituted phenoxycarbonyl, unsubstituted or substituted benzyloxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted aryloxy, unsubstituted or substituted arylthio, unsubstituted or substituted aryl-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted aryl-C.sub.1 -C.sub.4 -alkenyl, unsubstituted or substituted aryloxy-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted arylthio-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted hetaryl, unsubstituted or substituted hetaryloxy, unsubstituted or substituted hetarylthio, unsubstituted or substituted hetaryl-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted hetaryl-C.sub.2 -C.sub.4 -alkenyl, unsubstituted or substituted hetaryl-oxy-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocyclyloxy, N(R.sup.6).sub.2, where the radicals R.sup.6 are identical or different and are each H, C.sub.1 -C.sub.6 -alkyl or unsubstituted or substituted phenyl, or
--CO--N(R.sup.7).sub.2, where the radicals R.sup.7 are identical or different and are each H or C.sub.1 -C.sub.4 -alkyl, substituents, in addition to hydrogen, being halogen, cyano, 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.10 -alkoximino-C.sub.1 - or C.sub.2 -alkyl, aryl, aryloxy, benzyloxy, hetaryl, hetaryloxy, C.sub.3 -C.sub.6 -cycloalkyl, heterocyclyl or heterocyclyloxy, or
R.sup.3 and R.sup.4 together may form a carbocyclic or heterocyclic ring which may be substituted by the abovementioned substituents, and R.sup.3 or R.sup.4 may be halogen, or ##STR5## may be ##STR6##
where
n is an integer from 1 to 4, and
R.sup.8 is, or, when n>1, the R.sup.8 's are identical or different and are each, H, halogen, cyano, nitro or substituted or unsubstituted
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, aryl, aryloxy, benzyloxy, hetaryl or hetaryloxy,
have excellent fungicidal, insecticidal, nematicidal and acaricidal activity which is better than that of the known phenylacetic acid derivatives.
The fungicidal action is preferred.
The radicals stated for the general formula I may, for example, have the following meanings: X may be C.sub.1 -C.sub.4 -alkylidene (eg. methylidene, ethylidene, n- or isopropylidene, n-, iso-, sec- or tert-butylidene), C.sub.1 -C.sub.4 -alkoxymethylidene (eg. methoxy-, ethoxy-, n-propoxy, isopropoxy-, n-butoxy-, isobutoxy-, sec-butoxy- or tert-butoxymethylidene), C.sub.1 -C.sub.4 -alkylthiomethylidene (eg. methyl-, ethyl-, n-propyl-, isopropyl-, n-butylthio-, isobutylthio-, sec-butylthio- or tert-butylthiomethylidene) or C.sub.1 -C.sub.4 -alkoximino (eg. methoximino, ethoximino, n-propoximino, isopropoximino, n-butoximino, isobutoximino, sec-butoximino or tert-butoximino), Y may be O, S or NR.sup.5,
R.sup.1, R.sup.2 and R.sup.5 may each be H or C.sub.1 -C.sub.4 -alkyl (eg. methyl, ethyl, n- or isopropyl, n- or iso-, sec- or tert-butyl), Z.sup.1 and Z.sup.2 may be H, halogen (eg. fluorine, chlorine, bromine or iodine), methyl, methoxy or cyano, and
R.sup.3 and R.sup.4 may be identical or different and are each hydrogen, cyano, straight-chain or branched C.sub.1 -C.sub.10 -alkyl (eg. methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, n-, iso-, sec-, tert- or neopentyl, n-hexyl or n-decyl), C.sub.1 -C.sub.4 -haloalkyl (eg. trifluoromethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, fluorodichloromethyl, difluorochloromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2-chloroethyl, 2,2,2-trichloroethyl or pentachloroethyl),
C.sub.3 -C.sub.6 -cycloalkyl (eg. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl),
C.sub.3 -C.sub.6 -halocycloalkyl (eg. 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 -alkyl (eg. 1-methylcyclopropyl, 2,2-dimethylcyclopropyl or 1-methylcyclohexyl),
C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl (eg. methoxymethyl, ethoxymethyl, n- or isopropoxymethyl, n-, iso-, sec- or tert-butoxymethyl, 2-methoxyprop-2-yl, 2-ethoxyprop-2-yl, 2-n- or isopropoxyprop-2-yl or 2-n-, iso-, sec- or tert-butoxyprop-2-yl), C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.4 -alkyl (eg. methylthiomethyl, ethylthiomethyl, n- or isopropylthiomethyl, n-, iso-, sec- or tert-butylthiomethyl, 2-methylthioprop-2-yl, 2-ethylthioprop-2-yl, 2-n- or isopropylthioprop-2-yl or 2-n-, iso-, sec- or tert-butylthioprop-2-yl),
aryl(phenyl)thio-C.sub.1 -C.sub.4 -alkyl (eg. phenylthiomethyl or 2-chlorophenylthiomethyl),
C.sub.2 -C.sub.6 -alkenyl (eg. vinyl, 1-propenyl, 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 3-methyl-2-butenyl or 2-methyl-2-penten-5-yl),
C.sub.2 -C.sub.5 -haloalkenyl (eg. 2,2-difluorovinyl, 2,2-dichlorovinyl, 3,3,3-trifluoropropenyl, 3,3,3-trichloropropenyl or 3-chloro-2-propenyl),
C.sub.3 -C.sub.6 -cycloalkenyl (eg. cyclopent-1-enyl, cyclopentadienyl or cyclohex-1-enyl),
C.sub.3 -C.sub.6 -halocycloalkenyl (eg. pentafluorocyclopentadienyl or pentachlorocyclopentadienyl),
C.sub.2 -C.sub.4 -alkynyl (eg. ethynyl, 1-propynyl or 1-propargyl),
C.sub.1 -C.sub.4 -alkoxy (eg. methoxy, ethoxy, n- or isopropoxy or n-, iso-, sec- or tert-butoxy),
C.sub.1 -C.sub.4 -alkylthio (eg. methylthio, ethylthio, n- or isopropylthio or n-, iso-, sec- or tert-butylthio) or benzylthio,
C.sub.1 -C.sub.4 -haloalkoxy (eg. trifluoromethoxy, pentafluoroethoxy or 1,1,2,2-tetrafluoroethoxy),
N(R.sup.6).sub.2 (eg. amino, methylamino, dimethylamino, ethylamino, diethylamino, di-n-propylamino, diisopropylamino, di-n-butylamino or diisobutylamino),
C.sub.1 -C.sub.4 -alkylcarbonyl (eg. acetyl, propionyl, butyryl, isobutyryl or pivaloyl),
unsubstituted or substituted phenylcarbonyl (eg. benzoyl or 4-chlorobenzoyl),
unsubstituted or substituted benzylcarbonyl (eg. benzylcarbonyl),
C.sub.1 -C.sub.4 -alkoxycarbonyl (eg. methoxycarbonyl, ethoxycarbonyl,
n- or isopropoxycarbonyl or n-, iso-, sec- or tert-butoxycarbonyl),
unsubstituted or substituted phenoxycarbonyl (eg. phenoxycarbonyl or 4-chlorophenoxycarbonyl),
unsubstituted or substituted benzyloxycarbonyl (eg. benzyloxycarbonyl),
--CO--N(R.sup.7).sub.2 (eg. aminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, diisopropylaminocarbonyl, phenylaminocarbonyl or N-methyl-N-phenylaminocarbonyl),
unsubstituted or substituted aryl (eg. phenyl, naphthyl or anthryl),
unsubstituted or substituted aryloxy (eg. phenoxy, naphthyloxy or anthryloxy),
unsubstituted or substituted arylthio (eg. phenylthio),
unsubstituted or substituted aryl-C.sub.1 -C.sub.4 -alkyl ( eg. 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 aryl-C.sub.1 -C.sub.4 -alkenyl (eg. phenyl-1-ethenyl, 2-phenyl-1-propenyl, 2,2-diphenylethenyl, 1-phenyl-1-propen-2-yl or 1-phenyl-1-ethenyl), unsubstituted or substituted aryloxy-C.sub.1 -C.sub.4 -alkyl (eg. phenoxymethyl),
unsubstituted or substituted arylthio-C.sub.1 -C.sub.4 -alkyl (eg. phenylthiomethyl),
unsubstituted or substituted hetaryl (eg. pyridyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrimidinyl, 2,6-pyrimidinyl, 1,5-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 hetaryloxy (eg. 2-pyridyloxy or 2-pyrimidinyloxy),
unsubstituted or substituted hetarylthio (eg. 2-pyridylthio, 2-pyrimidinylthio or 2-benzothiazolylthio),
unsubstituted or substituted hetaryl-C.sub.1 -C.sub.4 -alkyl (eg. 2-pyridylmethyl or 3-pyridylmethyl),
unsubstituted or substituted hetaryloxy-C.sub.1 -C.sub.4 -alkyl (eg. furfurylmethoxy, thienylmethoxy, 3-isoxasolylmethoxy, 2-oxasolylmethoxy or 2-pyridylmethoxy),
unsubstituted or substituted hetaryl-C.sub.2 -C.sub.4 -alkenyl (eg. 2'-furyl-2-ethenyl, 2'-thienyl-2-ethenyl or 3'-pyridyl-2-ethenyl),
unsubstituted or substituted heterocyclyl (eg. 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) or
unsubstituted or substituted heterocyclyloxy (eg. 2-dihydropyranyloxy or 2-tetrahydropyranyloxy).
The radicals referred to above in connection with unsubstituted or substituted are, in addition to hydrogen, for example, 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-1-ethyl, n-pentyloximino-1-ethyl, n-hexyloximino-1-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 and tetrahydropyran-2-yloxy.
The group ##STR7## may also be the radical of a carbocyclic or heterocyclic oxime (eg. cyclopentanone oxime, cyclohexanone oxime, cycloheptanone oxime, 2-adamantanone oxime, D-camphor oxime, 1-tetralone oxime, 1-indanone oxime, 9-fluorenone oxime, 1-methyl-4-piperidone oxime, violuric acid or N,N-dimethylvioluric acid).
R.sup.3 and R.sup.4 together then form, for example, a cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralin, indane or fluorene ring.
One of the radicals R.sup.3 or R.sup.4 may furthermore be halogen (eg. fluorine, chlorine, bromine or iodine).
n may be 1, 2, 3 or 4 and R.sup.8 may be for example H, 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-tetrafluoromethoxy, phenyl, phenoxy, benzyloxy or pyrid-2-yl, where these radicals in turn may be substituted by fluorine, chlorine, bromine, iodine, cyano, methyl or methoxy.
Among the compounds in which R.sup.3 and R.sup.4 are hydrogen, the preferred compounds are those in which either only R.sup.3 or only R.sup.4 is hydrogen, in particular the compounds in which R.sup.3 is hydrogen.
Also preferred are compounds of the formula II in which x is CH.sub.2, CHCH.sub.3, CHC.sub.2 H.sub.5, CHOCH.sub.3, CHOC.sub.2 H.sub.5, CHSCH.sub.3 or CHSC.sub.2 H.sub.5, Y is 0, R.sup.1 is C.sub.1 -C.sub.4 -alkyl, R.sup.2 is H or methyl, R.sup.3 and R.sup.4 are identical or different and each is hydrogen, cyano, straight-chain or branched C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl, 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, arylthio-C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.2 -C.sub.4 -haloalkenyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C.sub.1 -C.sub.4 -alkyl, substituted or unsubstituted aryl-C.sub.2 -C.sub.4 -alkenyl, substituted or unsubstituted aryloxy-C.sub.1 -C.sub.4 -alkyl, substituted or unsubstituted hetaryl, substituted or unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio or substituted or unsubstituted heterocyclyl, or each is N(R.sup.6).sub.2, R.sup.6 being identical or different and denoting M, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl or substituted or unsubstituted phenyl, or each is --CO--N(R.sup.7).sub.2, R.sup.7 being identical or different and denoting H or C.sub.1 -C.sub.4 -alkyl, the term "substituted" denoting the radicals listed in claim 1, and R.sup.3 and R.sup.4 may together denote a carbocyclic or heterocyclic ring which may be substituted by the radicals given under "substituted", and R.sup.3 and R.sup.4 may be halogen, and Z.sup.1 and Z.sup.2 are hydrogen, fluorine, chlorine, bromine, iodine, methyl, cyano or methoxy.
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 compounds of the general formula I as claimed in claim 1 are prepared, for example, as described in Scheme 1 (Z.sup.1 and Z.sup.2 are each H). ##STR8##
The compounds of the general formula I in which X is CH.sub.2, CH-alkyl or CH-alkoxy can be prepared, for example, from the ketoesters 4 by a Wittig or Wittig-Horner reaction (cf. European Patents 348,766 and 178,826 and DE 3 705 389). The similar compounds 5 are likewise obtained from the ketoesters 2.
Alternatively, it is also possible to adopt a procedure in which compounds of the formula 7 or 9 are condensed with suitable reagents, for example with formaldehyde where X is CH.sub.2 (cf. DE 3317356), a) with aldehydes (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 (similarly to C. Jutz, Chem. Ber. 91 (1958), 1867) where X is CH-alkyl, or with a formate followed by alkylation (cf. European Patent 178,826) where X is CH--O-alkyl. Further preparation methods for the compounds of the formula 5 and I where X is CH--O-alkyl are described in European Patent 178,826.
Another possible method for preparing the compounds of the formula I where X is CH-alkyl and YR.sub.2 is COOAlk is to react ketene acetals with phenylchlorocarbenes (S. N. Slougui and G. Rousseau, Synth. Commun. 12 (5) (1982), 401-407).
For compounds of the general formula I where X is CH--S-alkyl, the preparation can be carried out by the methods described in European Patents 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 a known method, for example with chlorine, bromine or N-bromosuccinimide, in an inert solvent (eg. CCl.sub.4 or cyclohexane), with exposure to, for example, a Hg vapor lamp or in the presence of a free radical initiator, eg. dibenzoyl peroxide, or by introducing the radicals L, eg. mesylate, tosylate, acetate or triflate, via suitable intermediates (where L is halogen or OH).
The oxime ethers of the formula I where X is N-Oalkyl 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 (eg. an alkyl iodide, dialkyl sulfate, etc.) (cf. DE 3 623 921).
Furthermore, a phenylacetic ester of the formula 9 can be converted with a base (eg. NaOMe, NaH, K tertbutylate, etc.) in a solvent (eg. diethyl ether, toluene, tert-butanol, etc.) by a method similar to that in European Patent 254,426 into its anion and can be converted into the oxime with a suitable nitrosating agent (such as methyl nitrite, amyl nitrate, tert-butyl nitrite, etc.). The resulting oximate is alkylated with an alkylating agent (eg. an alkyl iodide or dialkyl sulfate).
The same processes 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.
In the preparation processes described above, Y-R.sup.1 is usually alkoxy.
The compounds in which YR.sup.1 is OH (11) 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 YR.sup.1 is COOAlkyl (10) (cf. Scheme 2): ##STR9##
Alternatively, the nitriles 12 can be converted in a known manner (cf. Organikum 16th edition, page 424 et seq. (1985) into the carboxylic acids 11.
The resulting carboxylic acids 11 can be converted in a conventional manner into the acyl chlorides 14 (cf. Organikum 16th edition, page 423 et seq. (1985). The conversion of 14 into the amides 15 is effected by methods similar to that described in Organikum 16th edition, page 412 (1985).
The thioesters 13 are obtained from the acyl chlorides 14 (similarly to Houben-Weyl Vol. 8, page 464 et seq. (1952)).
Alternatively, the thioesters 13 can also be prepared from the acids 11 (similarly to Houben-Weyl Vol. E5, page 855 et seq. (1985)).
The amides 15 in which R.sup.1 and R.sup.5 are each H can also be prepared from the nitriles 12 by processes known from the literature (cf. Synthesis 1980, 243).
The preparation of the compounds of the general formulae 2 and 7 with ortho-methyl substitution at the aromatic (R.sup.2 =H) is known.
(YR.sup.1 =OAlkyl; cf. European Patents 178,826 and 260,832).
The oximes required for the preparation of the compounds of the general formula I are either known or can be prepared by one of the processes shown in Scheme 3. ##STR10##
Methods for the conversion of 16 or 18 into 17 are described in Houben-Weyl, Vol. 10/4 (1968).
Furthermore, aldoximes 19 can be chlorinated by known methods and can be reacted with, for example, a cyanide to give the derivatives 17 (R.sup.4 =CN) (cf. M. R. Zimmermann J. f. prakt. Chemie 66 (1902), 359).
The specific derivatives in which R.sup.3 is CN and R.sup.4 is alkoxyalkyl are prepared according to European Patent 74,047, those in which R.sup.3 is CN and R.sup.4 is alkylthioalkyl according to European Patent 150,822 and those in which R.sup.3 is CN and R.sup.4 is alkyl according to DE 2 304 848.
The method employing Me.sub.3 SiO--NH--SiMe.sub.3 (R. U. Hoffmann and G. A. Buntain, Synthesis 1987, 831) is used for sterically hindered ketones. ##STR11##
The novel compounds of the general formula I as claimed in claim 1 are prepared, for example, by a method in which an oxime of the formula 17 is reacted with a substituted benzyl compound 6 in which L is a leaving group (eg. chloride, bromide, p-toluenesulfonate, methanesulfonate, triflate or acetate). R.sup.1 --R.sup.4, X and Y have the abovementioned meanings.
The reactions described can be carried out, for example, in an inert solvent (eg. acetone, acetonitrile, dimethyl sulfoxide, dimethylformamide, N-methylpyrrolidone or pyridine) with the use of a base (eg. sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, sodium hydride of sodium methylate).
The reactions can also be carried out in a two-phase system (eg. dichloromethane or water) with the aid of a suitable phase transfer catalyst (eg. cetyltrimethylammonium chloride or benzyltrimethylammonium chloride).
Another method for the preparation of compounds I (YR.sup.1 =OAlkyl, X=CH-OAlkyl or N-OAlkyl and L=Cl, Br, tosylate or mesylate) is illustrated by Scheme 5: ##STR12##
This synthesis sequence is carried out, as far as compound 22, similarly to the methods described in European Patent 244,786.
For example, N-hydroxyphthalimide can be converted with a halide or sulfonic ester 6 in the presence of an acid acceptor (eg. triethylamine, potassium carbonate, etc.), in a suitable solvent (eg. N-methylpyrrolidone, dimethylformamide, etc.), into the imidoether 21.
Cleavage to give the O-substituted hydroxylamine 22 can be effected with a mineral acid (eg. HCl; cf. Houben-Weyl Vol. 10/1, page 1181 et seq.) or with a base (for example with hydrazine or ethanolamine).
The conversion of amine 22 to I is carried out in a conventional manner (cf. D. Otzanak, J.C.S. Chem. Commun. 1986, 903).
The Examples and methods which follow are intended to illustrate the preparation of the novel active ingredients and of the novel intermediates.
Method 1: 3,4Dichloroacetophenone oxime
12.0 g (0.17 mol) of hydroxylammonium hydrochloride and 18.9 g (0.1 mol) of 3,4-dichloroacetophenone are added to a mixture of 20 ml of H.sub.2 O, 100 ml of methanol and 8 g (0.1 mol) of pyridine. Refluxing is carried out for 1 hour, after which the mixture is acidified with 2N HCl and extracted with 3.times.100 ml of tert-butyl methyl ether. The organic phase is washed with water, dried with Na.sub.2 So.sub.4 and evaporated down. 19.6 g (96% of theory) of crystals of melting point 92.degree. C., which according to .sup.1 H-NMR consist of 90% of trans-oxime, are obtained.
Method 2: 2-Oximino-2-tetrahydropyran-2'-ylacetonitrile
265.4 g (2.05 mol) of tetrahydrofuran-2-carbaldehyde oxime in 2 l of diethyl ether are initially taken at from -55.degree. to -60.degree. C. 153.5 g (2.15 mol) of chlorine are then passed in and the temperature is increased to -20.degree. C.; stirring is carried out for 1 hour, the mixture is then evaporated down in a rotary evaporator at 10.degree. C., the residue is taken up in 1.5 l of diethyl ether and the solution is stirred overnight in the absence of light, while cooling with ice. The solution is then filtered and the filtrate is added dropwise, while cooling with ice, to 147.3 g (2.27 mol) of potassium cyanide in 1 l of methanol at 10.degree.-15.degree. C. (exothermic). Stirring is carried out for 5 hours at room temperature (20.degree. C.), after which the precipitate is filtered off under suction and washed twice with diethyl ether. The organic phases are partitioned between tert-butyl methyl ether and water and the residue of the ether phases is crystallized from dichloromethane/n-hexane at 0.degree. C.
After filtration under suction and drying, 208 g (66% of theory) of a spectroscopically pure substance of melting point 105.degree.-106.degree. C. remain.
Method 3: 3-Methoxy-3-methyl-2-oximinobutyronitrile
53.6 g (0.46 mol) of 2-methoxy-2-methylpropionaldehyde oxime in ether (about 1M) are initially taken at from -5.degree. to -10.degree. C. 35.8 g (0.5 mol) of chlorine gas are passed in, after which stirring is carried out for 1 hour at this temperature and the mixture is then evaporated down at 10.degree. C. and the residue is taken up in diethyl ether. 24.7 g (0.5 mol) of sodium cyanide in 375 ml of 20:1 methanol/H.sub.2 O are initially taken at 10.degree. C. and the above ethereal solution is rapidly added dropwise. After 4 hours at room temperature, the mixture is filtered under suction and the residue is washed with twice 100 ml of methanol. The combined solutions are evaporated down and the residue is partitioned between methyl tert-butyl ether and water. Drying the organic phase over Na.sub.2 SO.sub.4, evaporating down and crystallizing from dichloromethane/n-hexane give 41.1 g (63% of theory) of a white powder of melting point 102.degree.-104.degree. C.
Method 4: Methyl 3-methoxy-2-[2'-(phthalimido-oxy)-methyl]-phenylacrylate
10 g (35 mmol) of methyl 3-methoxy-2-(2'-bromomethyl)-phenylacrylate, 5.7 g (35 mmol) of hydroxyphthalimide, 3.9 g (38.6 mmol) of triethylamine and 50 ml of N-methylpyrrolidone are combined and the mixture is stirred for 2 hours at 60.degree. C. It is then poured onto ice water, and the residue is filtered off under suction, washed with water and isopropanol and dried under reduced pressure. 9.0 g (70% of theory) of a crystalline product of melting point 156.degree.-158.degree. C. remain.
.sup.1 H-NMR (CDCl.sub.3): .delta.=3.60 (s, 3H); 3.75 (s, 3H); 5.12 (s, 2H); 7.13 (dbr, 1H); 7.35 (m, 2H); 7.62 (s, 1H); 7.7-7.9 (m, 5H)
Method 5: Methyl 3-methoxy-2-(2'-aminooxymethyl)-phenylacrylate
10.0 g (27 mmol) of the product from Method 4 are dissolved in 150 ml of methanol and the solution is stirred with 1.4 g (27 mmol) of hydrazine hydrate for 2 hours at room temperature. The precipitate is filtered off under suction, the mother liquor is evaporated down, the residue is stirred with diethyl ether, the precipitate is filtered off under suction again and the mother liquor is evaporated down. 6.0 g (92% of theory) of a yellow oil result (purity according to .sup.1 H-NMR about 90%). .sup.1 H-NMR (CDCl.sub.3): .delta.=3.71 (s, 3H); 3.80 (s, 3H); 4.60 (s, 2H); (5.35 (sbr, 2H); 7.0-7.50 (m, 4H); 7.58 (s, 1H).
Method 6: Methyl 2-methoximino-2-(2'-phthalimidooxymethyl)-phenylacetate
2.0 g (7 mmol) of methyl 2-methoximino-2-(2'-bromomethyl)-phenylacetate, 1.1 g (7 mmol) of hydroxyphthalimide and 0.8 g (7.7. mmol) of triethylamine are dissolved in 10 ml of N-methylpyrrolidone and the solution is stirred for 2 hours at 70.degree. C. For working up, ice water is added, and the crystals are filtered off under suction, washed with water and methyl tert-butyl ether and dried.
1.5 g (58% of theory) of crystals of melting point 152.degree.-155.degree. C. remain.
.sup.1 N-NMR (CDCl.sub.3): .delta.=3.83 (s, 3H); 3.98 (s, 3H); 5.07 (s, 2H); 7.15 (dbr, 1H); 7.45 (mc, 2H); 7.60-7.85 (m, 5H)
Method 7: Methyl 2-methoximino-2-(2'-aminooxymethyl)-phenylacetate
15.0 g (41 mmol) of the product from Method 6 are stirred with 2.1 g (42 mmol) of hydrazine hydrate in 150 ml of methanol for 2 hours at room temperature. The residue is again filtered off under suction, the mother liquor is evaporated down and triturated with diethyl ether, the residue is filtered off under suction and the mother liquor is evaporated down. 7.8 g (80% of theory) of an acid-sensitive oil remain.
.sup.1 H-NMR (CDCl.sub.3): .delta.=3.90 (s, 3H); 4.03 (s, 3H); 4.59 (s, 2H); 5.35 (sbr, 2H); 7.15 (dbr, 1H); 7.40 (sbr, 3H)

EXAMPLE 1
Methyl 3-methoxy-2-[2'-[1"-(3'", 5'"-dichlorophenyl)-1"-methyl]-iminooxymethyl]-phenylacrylate (No. 582, Table I)
0.6 g (25 mmol) of sodium hydride powder in 100 ml of acetonitrile is initially taken, 5.1 g (25 mmol) of 3,5-dichloroacetophenone oxime are added and the mixture is refluxed for 1 hour. Thereafter, 9.3 g (33 mmol) of methyl 2-(2'-bromomethyl)-phenyl-3-methoxyacrylate in 50 ml of acetonitrile are added dropwise and refluxing is continued for a further 4 hours. The mixture is evaporated down under reduced pressure and then partitioned between methyl tert-butyl ether and saturated ammonium chloride solution, the organic phase is washed with water and the residue obtained by evaporation is crystallized from methyl butyl ether/n-hexane. 4.6 g (45% of theory) of a substance of melting point 87.degree.-88.degree. C. are obtained.
.sup.1 H-NMR (CDCl.sub.3): .delta.=2.19 (s, 3H); 3.70 (s, 3H); 3.81 (s, 3H); 5.15 (s, 2H); 7.08 (m, 1H); 7.17 (m, 3H); 7.50 (m, 3H); 7.58 (s, 1H)
EXAMPLE 2
Methyl 3-methoxy-2-[2'-(1'-cyano-(-1"-methoxy-1"-methylethyl)-iminooxymethyl]-phenylacrylate (No. 36, Table I)
3.3 g (23 mmol) of 3-methoxy-3-methyl-2-oximinobutyronitrile, 6.6 g (23 mmol) of methyl 2-(2'-bromomethylphenyl)-3-methoxyacrylate and 3.2 g (23 mmol) of potassium carbonate in 60 ml of N,N-dimethylformamide are stirred for 15 hours at room temperature. The mixture is then evaporated down, the residue is taken up in ethyl acetate, the solution is washed with 3.times.50 ml of water and the organic phase is dried over sodium sulfate, evaporated down and chromatographed over silica gel using 40:1 toluene/ethyl acetate.
Yield: 7.0 g (88% of theory) of an oil.
IR (film): 1,285, 1,258, 1,189, 1,180, 1,131, 1,111, 1,069, 1,008 cm.sup.-1.
EXAMPLE 3
Methyl 2-methoximino-2-[2'-(1"-(3'", 5'"-dichlorophenyl)-1"-methyl)-iminooxymethyl]-phenylacetate (No. 582, Table II)
0.6 g (25 mmol) of NaH in 50 ml of acetonitrile is initially taken, and 5.1 g (25 mmol) of 3,5-dichloroacetophenone oxime are added at room temperature. Refluxing is carried out for 1 hour, after which 9.4 g (33 mmol) of methyl 2-methoximino-2-(2'-bromomethyl)phenylacetate in 50 ml of acetonitrile are added dropwise and refluxing is continued for a further 4 hours. After evaporating down, partitioning the residue between water/methyl tert-butyl ether, washing the organic phase with water, drying the organic phase with sodium sulfate and evaporating down, the residue is subjected to column chromatography over silica gel using methyl tert-butyl ether/hexane. 5.4 g (53% of theory) of crystals of melting point 95.degree.-97.degree. C. result.
.sup.1 H-NMR (CDCl.sub.3): .delta.=2.17 (s, 3H); 3.82 (s, 3H); 4.02 (s, 3H); 5.15 (s, 2H); 7.20 (dbr, 1H); 7.25-7.55 (m, 6H)
EXAMPLE 4
Methyl 3-methoxy-2-[2'-(1"-(4'"-bromophenyl)-1"-methyl)-iminooxymethyl]-phenylacrylate (No. 593, Table I)
2.37 g (10 mmol) of methyl 3-methoxy-2-(2'-aminooxymethyl)-phenylacrylate, 1.99 g (10 mmol) of 4-bromoacetophenone, 2 ml of water, 0.8 g of pyridine and 10 ml of methanol are combined and the mixture is stirred for 24 hours at room temperature. The mixture is evaporated down, the residue is partitioned between water/methyl tert-butyl ether and the organic phase is washed with 2N HCl and washed neutral with NaHCO.sub.3 and evaporated down, and the residue is chromatographed over SiO.sub.2 using methyl tert-butyl ether/hexane. 2.1 g (51% of theory) of crystals of melting point 105.degree.-107.degree. C. result. .sup.1 H-NMR (CDCl.sub.3): .delta.=2.22 (s, 3H); 3.70 (s, 3H); 3.80 (s, 3H); 5.15 (s, 2H); 7.16 (dbr, 1H); 7.33 (m, 2H); 7.45 (m, 5H); 7.58 (s, 1H)
EXAMPLE 5
Methyl 2-methoximino-2-[2'-(1"-(4'"-nitrophenyl)-1"-methyl)-iminooxymethyl]-phenylacetate (No. 614, Table II)
2.38 g (10 mmol) of methyl 2-methoximino-2-(2'-aminooxymethyl)-phenylacetate, 1.65 g (10 mmol) of 4-nitroacetophenone, 2 ml of water, 0.8 g of pyridine and 10 ml of methanol are reacted as in Example 4. 2.1 g (55% of theory) of crystals of melting point 87.degree.-89.degree. C. are obtained.
.sup.1 H-NMR (CDCl.sub.3): .delta.=2.22 (s, 3H); 3.81 (s, 3H); 4.02 (s, 3H); 5.18 (s, 2H); 7.20 (dd, 1H); 7.4 (m, 3H); 7.75 (dd, 2H); 8.18 (dd, 2H).
EXAMPLE 6
Methyl 3-methoxy-2-[2'-(1"-(4'"-chlorophenyl)-iminooxymethyl]-phenylacrylate (No. 95 Table 5)
a) 5.5 g (15 mmol) of methyl 3-methoxy-2-[2'-(phthalimidooxy)-methyl]-phenylacrylate (from Method 4 ) in 100 ml of methanol are initially taken, and 0.75 g (15 mmol) of hydrazine hydrate is added at room temperature. After 15 minutes at this temperature, the mixture is evaporated down, the residue is triturated with methyl tert-butyl ether and the cleavage product is filtered off under suction. The mother liquor is evaporated down, the residue is taken up with 50 ml of methanol and 2.1 g (15 mmol) of 4-chlorobenzaldehyde in 50 ml of methanol plus 1 drop of pyridine are added dropwise.
Stirring was carried out overnight at 23.degree. C., after which the product was filtered off under suction, washed with methanol and dried.
2.9 g (54% of theory) of crystals of melting point 87.degree.-89.degree. C. were obtained.
.sup.1 H-NMR (CDCl.sub.3): .delta.=3.66 (s, 3H); 3.80 (s, 3H); 5.13 (s, 2H); 7.17 (m, 1H); 7.35 (m, 4H); 7.50 (me, 3H); 7.60 (s, 1H); 8.06 (s, 1H).
b) 50 ml of methanol are slowly added to 1.3 g (55 mmol) of NaH powder under a nitrogen atmosphere (evolution of hydrogen). 7.8 g (50 mmol) of 4-chlorobenzaldehyde oxime in 50 ml of methanol are then added at room temperature. Stirring is carried out for half an hour, after which 14.3 g (50 mmol) of methyl 3-methoxy-2-(2'-bromomethyl)-phenylacrylate in 50 ml of methanol are added dropwise and stirring is carried out at room temperature for a further 48 hours. The white residue is filtered off under suction, washed with methanol and dried. 1.9 g (11% of theory) of a product of melting point 82.degree.-84.degree. C. are obtained.
EXAMPLE 7
Methyl 2-methoximino-2-(2'-phthalimidooxymethyl)-phenylacetate (No. 1, Table 8)
2.0 g (7 mmol) of methyl 2-methoxyimino-2-(2'-bromomethyl)-phenylacetate, 1.1 g (7 mmol) of hydroxyphthalimide and 0.8 g (7.7 mmol) of triethylamine are dissolved in 10 ml of N-methylpyrrolidone and the mixture is stirred for 2 hours at 70 .degree. C. Ice water is added and the crystals are filtered off under suction, washed with water and methyl tert-butyl ether and dried. There remain 1.5 g (58% of theory) of crystals of melting point 152.degree.-155.degree. C. .sup.1 H-NMR (CDCl.sub.3): .delta.=3.83 (s, 3H); 3.98 (s, 3H); 5.07 (s, 2H); 7.15 (dbr, 1H); 7.45 (mc, 2H); 7.60-7.85 (m, 5H).
The compounds listed in Tables I-IX can be prepared in a similar manner.
TABLE I__________________________________________________________________________ ##STR13##No. R.sup.3 R.sup.4 Data__________________________________________________________________________ 1 Cl Phenyl 2 Cl Cyano 3 Cl Ethoxycarbonyl 4 Cl Cyclopropyl 5 CF.sub.3 CF.sub.3 6 CF.sub.3 Phenyl 7 CCl.sub.3 CCl.sub.3 8 CCl.sub.3 Phenyl 9 CH.sub.2 Cl Phenyl 10 CF.sub.2 CF.sub.3 Phenyl 11 CF.sub.2 Cl Phenyl 12 CHCl.sub.2 Phenyl 13 Cyclopropyl Cyclopropyl 14 Cyclopropyl Phenyl oil; IR (film): 1190, 1129, 1056, 1032, 768 15 Cyclopropyl 4-Fluorophenyl oil; IR (film): 1508, 1225, 1129, 998, 839 16 Cyclopropyl 4-Chlorophenyl oil; IR (film): 1490, 1129, 1091, 1014, 1800 17 Cyclopropyl 4-Methoxyphenyl oil; IR (film): 1251, 1177, 1129, 1033 18 Cyclopropyl 4-Ethoxyphenyl 19 Cyclopropyl 4-Phenoxyphenyl 20 Cyclopropyl Pentachlorophenyl 21 Cyclopropyl Pentafluorophenyl 22 Cyclopentyl Phenyl 23 Cyclohexyl Phenyl 24 Phenyl 2,2-Dichloro-1-methylcyclopropyl 25 Phenyl 2,2-Difluorocyclopropyl 26 Phenyl 2,2-Dichlorocyclopropyl 27 Phenyl 2,2-Dibromocyclopropyl 28 Phenyl 2,2,3,3-Tetrafluorocyclobutyl 29 Phenyl 2,2-Dimethylcyclopropyl 30 Phenyl 1-Methylcyclohexyl 31 CN Methoxymethyl 32 CN Ethoxymethyl 33 CN n-Propoxymethyl 34 CN iso-Propoxymethyl 35 CN tert.-Butoxymethyl 36 CN 2-Methoxyprop-2-yl oil; IR (film): 1436, 1191, 1131, 1057, 1003 37 CN 2-Ethoxyprop-2-yl oil; IR (film): 1191, 1177, 1131, 1095, 1010 38 CN 2-n-Propoxyprop-2-yl oil; IR (film): 1191, 1175, 1131, 1060, 1005 39 CN 2-iso-Propoxyprop-2-yl oil; IR (film): 1370, 1191, 1172, 1131, 998 40 CN 2-tert.-Butoxyprop-2-yl 41 CN Methylthiomethyl 42 CN tert.-Butylthiomethyl 43 CN 2-Methylthioprop-2-yl oil; IR (film): 1436, 1191, 1131, 1114, 1016, 998 44 CN 2-iso-Propylthioprop-2-yl 45 CN 2-tert.-Butylthioprop-2-yl oil; IR (film): 1366, 1191, 1132, 1113, 1012, 1000 46 CN Methyl 47 CN Ethyl 48 CN n-Propyl 49 CN iso-Propyl oil; IR (film): 1285, 1258, 1189, 1131, 1111, 1069, 1008 50 CN n-Butyl 51 CN iso-Butyl 52 CN sec.-Butyl 53 CN tert.-Butyl 54 CN n-Hexyl 55 CN n-Decyl 56 CN Cyclopropyl oil; IR (film): 1207, 1190, 1130, 1057, 1003 57 CN Cyclohexyl 58 CN Phenylthiomethyl 59 CN 2-Phenylthiomethyl 60 CN 2-(2'-Chlorophenylthio)prop-2-yl 61 CN Ethynyl 62 CN 1-Propynyl 63 CN Methoxy 64 CN Ethoxy 65 CN n-Propoxy 66 CN iso-Propoxy 67 CN n-Butoxy 68 CN iso-Butoxy 69 CN sec.-Butoxy 70 CN tert.-Butoxy 71 CN Methylthio 72 CN Ethylthio 73 CN n-Propylthio 74 CN iso-Propylthio 75 CN n-Butylthio 76 CN iso-Butylthio 77 CN sec.-Butylthio 78 CN tert.-Butylthio 79 CN Benzylthio 80 CN Trifluoromethoxy 81 CN Cyano 82 CN Amino 83 CN Methylamino 84 CN Dimethylamino 85 CN Ethylamino 86 CN Diethylamino 87 CN Di-n-Propylamino 88 CN Di-iso-Propylamino 89 CN Di-n-Butylamino 90 CN Di-iso-Butylamino 91 CN Acetyl 92 CN Propion-1-yl 93 CN Butyr-1-yl 94 CN iso-Butyr-1-yl 95 CN Pivaloyl 96 CN Benzoyl 97 CN 4-Chlorobenzoyl 98 CN Benzylcarbonyl 99 CN Methoxycarbonyl100 CN Ethoxycarbonyl101 CN n-Propoxycarbonyl102 CN iso-Propoxycarbonyl103 CN n-Butoxycarbonyl104 CN iso-Butoxycarbonyl105 CN sec.-Butoxycarbonyl106 CN tert.-Butoxycarbonyl107 CN n-Hexoxycarbonyl108 CN Phenoxycarbonyl109 CN 4-Chlorophenoxycarbonyl110 CN Benzyloxycarbonyl111 CN Aminocarbonyl112 CN Dimethylaminocarbonyl113 CN Diethylaminocarbonyl114 CN Di-iso-Propylaminocarbonyl115 CN Phenylaminocarbonyl116 CN N-Methyl-N-Phenylaminocarbonyl117 CN Phenyl oil; IR (film): 1245, 1127, 1024, 1015, 767, 750118 CN 2-Fluorophenyl119 CN 3-Fluorophenyl120 CN 4-Fluorophenyl121 CN Pentafluorophenyl122 CN 2-Chlorophenyl123 CN 3-Chlorophenyl124 CN 4-Chlorophenyl125 CN Pentachlorophenyl126 CN 2,3-Dichlorophenyl127 CN 2,4-Dichlorophenyl128 CN 2,5-Dichlorophenyl129 CN 2,6-Dichlorophenyl130 CN 3,4-Dichlorophenyl131 CN 3,5-Dichlorophenyl132 CN 2,3,4-Trichlorophenyl133 CN 2,3,5-Trichlorophenyl134 CN 2,3,6-Trichlorophenyl135 CN 2,4,5-Trichlorophenyl136 CN 2,4,6-Trichlorophenyl137 CN 3,4,5-Trichlorophenyl138 CN 2,3,4,6-Tetrachlorophenyl139 CN 2,3,5-6-Tetrachlorophenyl140 CN 2-Bromophenyl141 CN 3-Bromophenyl142 CN 4-Bromophenyl143 CN 2,4-Dibromophenyl144 CN 3-Bromo-4-fluorophenyl145 CN 3-Bromo-4-methoxyphenyl146 CN 2-Iodophenyl147 CN 3-Iodophenyl148 CN 4-Iodophenyl149 CN 2-Chloro-4-fluorophenyl150 CN 2-Chloro-5-fluorophenyl151 CN 2-Chloro-6-fluorophenyl152 CN 2-Chloro-4-bromophenyl153 CN 2-Bromo-4-chlorophenyl154 CN 2-Bromo-4-fluorophenyl155 CN 3-Bromo-4-chlorophenyl156 CN 3-Chloro-4-fluorophenyl157 CN 3-Fluoro-4-chlorophenyl158 CN 2-Cyanophenyl159 CN 3-Cyanophenyl160 CN 4-Cyanophenyl161 CN 2-Nitrophenyl162 CN 3-Nitrophenyl163 CN 4-Nitrophenyl164 CN 2-Methylphenyl165 CN 3-Methylphenyl166 CN 4-Methylphenyl167 CN 2,4-Dimethylphenyl168 CN 2,6-Dimethylphenyl169 CN 3,4-Dimethylphenyl170 CN 3,5-Dimethylphenyl171 CN 2,3,4-Trimethylphenyl172 CN 2,3,5-Trimethylphenyl173 CN 2,3,6-Trimethylphenyl174 CN 2,4,5-Trimethylphenyl175 CN 2,4,6-Trimethylphenyl176 CN 3,4,5-Trimethylphenyl177 CN Pentamethylphenyl178 CN 2-Ethylphenyl179 CN 3-Ethylphenyl180 CN 4-Ethylphenyl181 CN 3,5-Diethylphenyl182 CN 2-n-Propylphenyl183 CN 3-n-Propylphenyl184 CN 4-n-Propylphenyl185 CN 2-iso-Propylphenyl186 CN 3-iso-Propylphenyl187 CN 4-iso-Propylphenyl188 CN 2,4-Di-iso-Propylphenyl189 CN 3,5-Di-iso-Propylphenyl190 CN 4-n-Butylphenyl191 CN 4-sec.-Butylphenyl192 CN 4-iso-Butylphenyl193 CN 4-tert.-Butylphenyl194 CN 3-tert.-Butylphenyl195 CN 2-tert.-Butylphenyl196 CN 2,4-Di-tert.-Butylphenyl197 CN 3,5-Di-tert.-Butylphenyl198 CN 4-n-Hexylphenyl199 CN 4-n-Dodecylphenyl200 CN 2-Methyl-4-tert.-Butylphenyl201 CN 2-Methyl-6-tert.-Butylphenyl202 CN 2-Methyl-4-iso-Propylphenyl203 CN 2-Methyl-4-Cyclohexylphenyl204 CN 2-Methyl-4-Phenylphenyl205 CN 2-Methyl-4-Benzylphenyl206 CN 2-Methyl-4-Phenoxyphenyl207 CN 2-Methyl-4-Benzyloxyphenyl208 CN 2-Methyl-3-Chlorophenyl209 CN 2-Methyl-4-Chlorophenyl210 CN 2-Methyl-5-Chlorophenyl211 CN 2-Methyl-6-Chlorophenyl212 CN 2-Methyl-4-Fluorophenyl213 CN 2-Methyl-3-Bromophenyl214 CN 2-Methyl-4-Bromophenyl215 CN 2-Methyl-3-Methoxyphenyl216 CN 2-Methyl-4-Methoxyphenyl217 CN 2-Methyl-5-methoxyphenyl218 CN 2-Methyl-6-methoxyphenyl219 CN 2-Methyl-4-iso-Propoxyphenyl220 CN 2-Methyl-2,5-dimethoxyphenyl221 CN 2-Methoxyphenyl222 CN 3-Methoxyphenyl223 CN 4-Methoxyphenyl224 CN 2,3-Dimethoxyphenyl225 CN 2,4-Dimethoxyphenyl226 CN 2,5-Dimethoxyphenyl227 CN 2,6-Dimethoxyphenyl228 CN 3,4-Dimethoxyphenyl229 CN 3,5-Dimethoxyphenyl230 CN 3,6-Dimethoxyphenyl231 CN 2,3,4-Trimethoxyphenyl232 CN 2,3,5-Trimethoxyphenyl233 CN 2,3,6-Trimethoxyphenyl234 CN 2,4,5-Trimethoxyphenyl235 CN 2,4,6-Trimethoxyphenyl236 CN 3,4,5-Trimethoxyphenyl237 CN 2-Ethoxyphenyl238 CN 3-Ethoxyphenyl239 CN 4-Ethoxyphenyl240 CN 2-iso-Propoxyphenyl241 CN 3-iso-Propoxyphenyl242 CN 4-iso-Propoxyphenyl243 CN 3-tert.-Butoxyphenyl244 CN 4-tert.-Butoxyphenyl245 CN 2-Trifluoromethoxyphenyl246 CN 3-Trifluoromethoxyphenyl247 CN 4-Trifluoromethoxyphenyl248 CN 3-(1',1',2',2'-Tetrafluoro)ethoxyphenyl249 CN 4-(1',1',2',2'-Tetrafluoro)ethoxyphenyl250 CN 2-Chloromethylphenyl251 CN 3-Chloromethylphenyl252 CN 4-Chloromethylphenyl253 CN 2-Trifluoromethylphenyl254 CN 3-Trifluoromethylphenyl255 CN 4-Trifluoromethylphenyl256 CN 2-(Methoxyiminomethyl)phenyl257 CN 3-(Methoxyiminomethyl)phenyl258 CN 4-(Methoxyiminomethyl)phenyl259 CN 2-(Ethoxyiminomethyl)phenyl260 CN 3-(Ethoxyiminomethyi)phenyl261 CN 4-(Ethoxyiminomethyl)phenyl262 CN 2-(n-Propoxyiminomethyl)phenyl263 CN 3-(n-Propoxyiminomethyl)phenyl264 CN 4-(n-Propoxyiminomethyl)phenyl265 CN 2-(iso-Propoxyiminomethyl)phenyl266 CN 3-(iso-Propoxyiminomethyl)phenyl267 CN 4-(iso-Propoxylminomethyl)phenyl268 CN 2-(n-Butoxyiminomethyl)phenyl269 CN 3-(n-Butoxylminomethyl)phenyl270 CN 4-(n-Butoxyiminomethyl)phenyl271 CN 2-(iso-Butoxyiminomethyl)phenyl272 CN 3-(iso-Butoxylminomethyl)phenyl273 CN 4-(iso-Butoxyiminomethyl)phenyl274 CN 2-(tert.-Butoxyiminomethyl)phenyl275 CN 3-(tert.-Butoxylminomethyl)phenyl276 CN 4-(tert.-Butoxylminomethyl)phenyl277 CN 2-(n-Pentoxyiminomethyl)phenyl279 CN 4-(n-Pentoxyiminomethyl)phenyl280 CN 2-(n-Hexoxyiminomethyl)phenyl281 CN 3-(n-Hexoxyiminomethyl)phenyl282 CN 4-(n-Hexoxyiminomethyl)phenyl283 CN 2-(Allyloxyiminomethyl)phenyl284 CN 3-(Allyloxyiminomethyl)phenyl285 CN 4-(Allyloxyiminomethyl)phenyl286 CN 2-(Benzyloxyiminomethyl)phenyl287 CN 3-(Benzyloxyiminomethyl)phenyl288 CN 4-(Benzyloxyiminomethyl)phenyl289 CN 2-(Methoxyimino-1'-ethyl)phenyl290 CN 3-(Methoxyimino-1'-ethyl)phenyl291 CN 4-(Methoxyimino-1'-ethyl)phenyl292 CN 2-(Ethoxyimino-1'-ethyl)phenyl293 CN 3-(Ethoxyimino-1'-ethyl)phenyl294 CN 4-(Ethoxyimino-1'-ethyl)phenyl295 CN 2-(n-Propoxyimino-1'-ethyl)phenyl296 CN 3-(n-Propoxyimino-1'-ethyl)phenyl297 CN 4-(n-Propoxyimino-1'-ethyl)phenyl298 CN 2-(n-Butoxyamino-1'-ethyl)phenyl299 CN 3-(n-Butoxyamino-1'-ethyl)phenyl300 CN 4-(n-Butoxyamino-1'-ethyl)phenyl301 CN 2-(n-Pentoxyimino-1'-ethyl)phenyl302 CN 3-(n-Pentoxyimino-1'-ethyl)phenyl303 CN 4-(n-Pentoxyimino-1'-ethyl)phenyl304 CN 2-(n-Hexoxyimino-1'-ethyl)phenyl305 CN 3-(n-Hexoxyimino-1'-ethyl)phenyl306 CN 4-(n-Hexoxyimino-1'-ethyl)phenyl307 CN 2-(Allyloxyimino-1'-ethyl)phenyl308 CN 3-(Allyloxyimino-1'-ethyl)phenyl309 CN 4-(Allyloxyimino-1'-ethyl)phenyl310 CN 2-(Benzyloxyimino-1'-ethyl)phenyl311 CN 3-(Benzyloxyimino-1'-ethyl)phenyl312 CN 4-(Benzyloxyimino-1'-ethyl)phenyl313 CN 2-Phenylphenyl314 CN 3-Phenylphenyl315 CN 4-Phenylphenyl316 CN 2-Phenoxyphenyl317 CN 3-Phenoxyphenyl318 CN 4-Phenoxyphenyl319 CN 2-Benzyloxyphenyl320 CN 3-Benzyloxyphenyl321 CN 4-Benzyloxyphenyl322 CN 4-(Imidazol-1'-yl)phenyl323 CN 4-(Piperazin-1'-yl)phenyl324 CN 4-(Morpholin-1'-yl)phenyl325 CN 4-(Piperidin-1'-yl)phenyl326 CN 4-(Pyridyl-2'-oxy)phenyl327 CN 2-Cyclopropylphenyl328 CN 3-Cyclopropylphenyl329 CN 4-Cyclopropylphenyl330 CN 3-Cyclohexylphenyl331 CN 4-Cyclohexylphenyl332 CN 4-Oxiranylphenyl333 CN 4-(1',3'-Dioxan-2'-yl)phenyl334 CN 4-(Tetrahydropyran-2-yloxy)phenyl335 CN 1-Naphthyl336 CN 2-Naphthyl337 CN 9-Anthryl338 CN 1-Naphtoxy339 CN 2-Naphtoxy340 CN 9-Anthroxy341 CN Phenoxy342 CN 2-Chlorophenoxy343 CN 3-Chlorophenoxy344 CN 4-Chlorophenoxy345 CN 4-Methylphenoxy346 CN 4-tert.-Butylphenoxy347 CN 4-Methoxyphenoxy348 CN 4-Ethoxyphenoxy349 CN 4-tert.-Butoxyphenoxy350 CN Phenylthio351 CN 2-Chlorophenylthio352 CN 4-Chlorophenylthio353 CN Benzyl354 CN 2-Methylbenzyl355 CN 3-Methylbenzyl356 CN 4-Methylbenzyl357 CN 4-tert.-Butylbenzyl358 CN 2-Chlorobenzyl359 CN 3-Chlorobenzyl360 CN 4-Chlorobenzyl361 CN 2,4-Dichlorobenzyl362 CN 2,6-Dichiorobenzyl363 CN 2,4,6-Trichlorobenzyl364 CN 2-Trifluoromethylbenzyl365 CN 3-Trifluoromethylbenzyl366 CN 4-Trifluoromethylbenzyl367 CN 2-Methoxybenzyl368 CN 4-Methoxybenzyl369 CN 4-tert.-Butoxybenzyl370 CN 4-Phenoxybenzyl371 CN 1-Phenethyl372 CN 2-Phenethyl373 CN 1-Phenylpropyl374 CN 2-Phenylpropyl375 CN 3-Phenylpropyl376 CN 2-Methyl-2-phenylpropyl377 CN 2-methyl-3-phenylpropyl378 CN 4-Phenylbutyl379 CN 2-Phenyl-1-ethenyl380 CN 1-Phenyl-1-ethenyl381 CN 1-Phenyl-1-propenyl382 CN 1-Phenyl-1-propen-2-yl383 CN 2,2-Diphenylethenyl384 CN Phenoxymethyl385 CN 2-Pyridyl386 CN 3-Pyridyl387 CN 4-Pyridyl388 CN 2,6-Pyrimidinyl389 CN 1,5-Pyrimidinyl390 CN 2-Thienyl391 CN 3-Thienyl392 CN 2-Furyl393 CN 3-Furyl394 CN 1-Pyrrolyl395 CN 1-Imidazolyl396 CN 1,2,4-Triazolyl397 CN 1,3,4-Triazolyl398 CN 4-Thiazolyl399 CN 2-Benzothiazolyl400 CN 2-Pyridyloxy401 CN 2-Pyrimidinyloxy402 CN 2-Pyridylthio403 CN 2-Pyrimidinylthio404 CN 2-Benzothiazolylthio405 CN Phenylthiomethyl406 CN 2-Pyridylmethyl407 CN 3-Pyridylmethyl408 CN Furfuryloxy409 CN Thienylmethoxy410 CN 3-Isoxazolylmethoxy411 CN 2-Oxazolylmethoxy412 CN 2-Pyridylmethoxy413 CN 2'-Furyl-2-ethenyl414 CN 2'-Thienyl-2-ethenyl415 CN 3'-Pyridyl-2-ethenyl416 CN Oxiranyl417 CN 1-Aziridinyl418 CN 1-Azetidinyl419 CN 1-Pyrrolidinyl420 CN 2-Tetrahydrofuryl421 CN 2-Tetrahydropyranyl422 CN 3-Tetrahydropyranyl423 CN 1-Piperidinyl424 CN 1-Morpholinyl425 CN 1-Piperazinyl426 CN 1,3-Dioxan-2-yl427 CN 3-Tetrahydrothiopyranyl428 CN 2-Dihydropyranytoxy429 CN 2-Tetrahydropyranytoxy oil; IR (film): 12051131, 1087, 1047, 1004430 CN (CH.sub.2).sub.4431 CN (CH.sub.2).sub.5432 CN (CH.sub.2).sub.6433 CN434 CN435 CN ##STR14##436 CN ##STR15##437 CN ##STR16##438 CN ##STR17##439 CN ##STR18##440 CN ##STR19##441 CN CF.sub.3442 CN 2-Fluoroethyl443 CN 2,2,2-Trifluoroethyl444 CN Pentafluoroethyl445 CN Chloromethyl446 CN Dichloromethyl447 CN Trichloromethyl448 CN 2-Chloroethyl449 CN 2,2,2-Trichloroethyl450 CN Pentachloroethyl451 CN Cyclopropyl452 CN Cyclobutyl453 CN Cyclopentyl454 CN Cyclohexyl455 CN 1-Methylcyclopropyl456 CN 2,2-Dimethylcyclopropyl457 CN 1-Methylcyclohexyl458 CN 2,2-Difluorocyclopropyl459 CN 2,2-Dichlorocyclopropyl460 CN 2,2-Dibromocyclopropyl461 CN 2,2-Dichloro-3-methylcyclopropyl462 CN 2,2,3,3-Tetrafluorocyclobutyl463 CN Ethenyl464 CN 1-Propenyl465 CN 2-Methyl-1-propenyl466 CN 4-Methylpent-3-en-1-yl467 CN 2-Propenyl468 CN 2-Butenyl469 CN 1-Methyl-2-propenyl470 CN 3-Methyl-2-butenyl471 CN 2,2-Difluoroethenyl472 CN 2,2-Dichloroethenyl473 CN 3,3,3-Trifluoropropenyl474 CN 3,3,3-Trichloropropenyl475 CN 3-Chloro-2-propenyl476 CN Cyclopent-1-enyl477 CN Cyclopentadienyl478 CN Cyclohex-1-enyl479 CN Pentafluorocyclopentadienyl480 CN Pentachlorocyclopentadienyl481 CN Styryl482 CH.sub.3 Methoxymethyl483 CH.sub.3 Ethoxymethyl484 CH.sub.3 n-Propoxymethyl485 CH.sub.3 iso-Propoxymethyl486 CH.sub.3 tert.-Butoxymethyl487 CH.sub.3 2-Methoxyprop-2-yl488 CH.sub.3 2-Ethoxyprop-2-yl489 CH.sub.3 2-n-Propoxyprop-2-yl490 CH.sub.3 2-iso-Propoxyprop-2-yl491 CH.sub.3 2-tert.-Butoxyprop-2-yl492 CH.sub.3 Methylthiomethyl493 CH.sub.3 tert.-Butylthiomethyl494 CH.sub.3 2-Methylthioprop-2-yl495 CH.sub.3 2-iso-Propylthioprop-2-yl496 CH.sub.3 2-tert.-Butylthioprop-2-yl497 CH.sub.3 Methyl498 CH.sub.3 Ethyl499 CH.sub.3 n-Propyl500 CH.sub.3 iso-Propyl501 CH.sub.3 n-Butyl502 CH.sub.3 iso-Butyl503 CH.sub.3 sec.-Butyl504 CH.sub.3 tert.-Butyl505 CH.sub.3 n-Hexyl506 CH.sub.3 n-Decyl507 CH.sub.3 Cyclopropyl508 CH.sub.3 Cyclohexyl509 CH.sub.3 Phenylthiomethyl510 CH.sub.3 2-Phenylthiomethyl511 CH.sub.3 2-(2'-Chlorophenylthio)prop-2-yl512 CH.sub.3 Ethynyl513 CH.sub.3 1-Propynyl514 CH.sub.3 Methoxy515 CH.sub.3 Ethoxy516 CH.sub.3 n-Propoxy517 CH.sub.3 iso-Propoxy518 CH.sub.3 n-Butoxy519 CH.sub.3 iso-Butoxy520 CH.sub.3 sec.-Butoxy521 CH.sub.3 tert.-Butoxy522 CH.sub.3 methylthio523 CH.sub.3 Ethylthio524 CH.sub.3 n-Propylthio525 CH.sub.3 iso-Propylthio526 CH.sub.3 n-Butylthio527 CH.sub.3 iso-Butylthio528 CH.sub.3 sec.-Butylthio529 CH.sub.3 tert.-Butylthio530 CH.sub.3 Benzylthio531 CH.sub.3 Trifluoromethoxy532 CH.sub.3 Cyano533 CH.sub.3 Amino534 CH.sub.3 Methylamino535 CH.sub.3 Dimethylamino536 CH.sub.3 Ethylamino537 CH.sub.3 Diethylamino538 CH.sub.3 Di-n-Propylamino539 CH.sub.3 Di-iso-Propylamino540 CH.sub.3 Di-n-Butylamino541 CH.sub.3 Di-iso-Butylamino542 CH.sub.3 Acetyl543 CH.sub.3 Propion-1-yl544 CH.sub.3 Butyr-1-yl545 CH.sub.3 iso-Butyr-1-yl546 CH.sub.3 Pivaloyl547 CH.sub.3 Benzoyl548 CH.sub.3 4-Chlorobenzoyl549 CH.sub.3 Benzylcarbonyl550 CH.sub.3 Methoxycarbonyl551 CH.sub.3 Ethoxycarbonyl552 CH.sub.3 n-Propoxycarbonyl553 CH.sub.3 iso-Propoxycarbonyl554 CH.sub.3 n-Butoxycarbonyl555 CH.sub.3 iso-Butoxycarbonyl556 CH.sub.3 sec.-Butoxycarbonyl557 CH.sub.3 tert.-Butoxycarbonyl558 CH.sub.3 n-Hexoxycarbonyl559 CH.sub.3 Phenoxycarbonyl560 CH.sub.3 4-Chlorophenoxycarbonyl561 CH.sub.3 Benzyloxycarbonyl562 CH.sub.3 Aminocarbonyl563 CH.sub.3 Dimethylaminocarbonyl564 CH.sub.3 Diethylaminocarbonyl565 CH.sub.3 Di-iso-Propylaminocarbonyl566 CH.sub.3 Phenylaminocarbonyl567 CH.sub.3 N-Methyl-N-Phenylaminocarbonyl568 CH.sub.3 Phenyl569 CH.sub.3 2-Fluorophenyl oil; IR (film): 1708, 1634, 1257, 1129, 761570 CH.sub.3 3-Fluorophenyl571 CH.sub.3 4-Fluorophenyl m.p.: 67-68.degree. C.;572 CH.sub.3 Pentafluorophenyl573 CH.sub.3 2-Chlorophenyl oil.: --574 CH.sub.3 3-Chlorophenyl575 CH.sub.3 4-Chlorophenyl576 CH.sub.3 Pentachlorophenyl577 CH.sub.3 2,3-Dichlorophenyl578 CH.sub.3 2,4-Dichlorophenyl oil; IR (film): 1708, 1634, 1256, 1129579 CH.sub.3 2,5-Dichlorophenyl m.p.: 80-2.degree. C.; IR; (KBr): 1704, 1634, 1250, 1132, 934, 766580 CH.sub.3 2,6-Dichlorophenyl581 CH.sub.3 3,4-Dichlorophenyl582 CH.sub.3 3,5-Dichlorophenyl m.p.: 87-88.degree. C.; IR (KBr): 1699, 1303, 1071, 1015, 932, 835583 CH.sub.3 2,3,4-Trichlorophenyl oil; IR (film): 1709, 1627, 1257, 1131, 1109584 CH.sub.3 2,3,5-Trichlorophenyl585 CH.sub.3 2,3,6-Trichlorophenyl586 CH.sub.3 2,4,5-Trichlorophenyl587 CH.sub.3 2,4,6-Trichlorophenyl588 CH.sub.3 3,4,5-Trichlorophenyl589 CH.sub.3 2,3,4,6-Tetrachlorophenyl590 CH.sub.3 2,3,5,6-Tetrachlorophenyl591 CH.sub.3 2-Bromophenyl592 CH.sub.3 3-Bromophenyl m.p.: 60-2.degree. C.; IR (KBr): 1708, 1635, 1253, 1129, 1113, 933, 773593 CH.sub.3 4-Bromophenyl m.p.: 104-6.degree. C.; IR (KBr): 1694, 1620, 1296, 1264, 1035, 938594 CH.sub.3 2,4-Dibromophenyl595 CH.sub.3 3-Bromo-4-Fluorophenyl596 CH.sub.3 3-Bromo-4-Methoxyphenyl597 CH.sub.3 2-iodophenyl598 CH.sub.3 3-iodophenyl599 CH.sub.3 4-iodophenyl600 CH.sub.3 2-Chloro-4-fluorophenyl601 CH.sub.3 2-Chloro-5-fluorophenyl602 CH.sub.3 2-Chloro-6-fluorophenyl603 CH.sub.3 2-Chloro-4-bromophenyl604 CH.sub.3 2-Bromo-4-chlorophenyl605 CH.sub.3 2-Bromo-4-fluorophenyl606 CH.sub.3 3-Bromo-4-chlorophenyl607 CH.sub.3 3-Chloro-4-fluorophenyl608 CH.sub.3 3-Fluoro-4-chlorophenyl609 CH.sub.3 2-Cyanophenyl610 CH.sub.3 3-Cyanophenyl611 CH.sub.3 4-Cyanophenyl612 CH.sub.3 2-Nitrophenyl613 CH.sub.3 3-Nitrophenyl614 CH.sub.3 4-Nitrophenyl615 CH.sub.3 2-Methylphenyl616 CH.sub.3 3-Methylphenyl oil; IR (film): 1709, 1634, 1256, 1129617 CH.sub.3 4-Methylphenyl m.p.: 73-75.degree. C.; IR (KBr): 1696, 1625, 1262, 1127, 1037, 930618 CH.sub.3 2,4-Dimethylphenyl619 CH.sub.3 2,6-Dimethylphenyl620 CH.sub.3 3,4-Dimethylphenyl621 CH.sub.3 3,5-Dimethylphenyl622 CH.sub.3 2,3,4-Trimethylphenyl623 CH.sub.3 2,3,5-Trimethylphenyl624 CH.sub.3 2,3,6-Trimethylphenyl625 CH.sub.3 2,4,5-Trimethylphenyl626 CH.sub.3 2,4,6-Trimethylphenyl627 CH.sub.3 3,4,5-Trimethylphenyl628 CH.sub.3 Pentamethylphenyl629 CH.sub.3 2-Ethylphenyl630 CH.sub.3 3-Ethylphenyl631 CH.sub.3 4-Ethylphenyl632 CH.sub.3 3,5-Diethylphenyl633 CH.sub.3 2-n-Propylphenyl634 CH.sub.3 3-n-Propylphenyl635 CH.sub.3 4-n-Propylphenyl636 CH.sub.3 2-iso-Propylphenyl637 CH.sub.3 3-iso-Propylphenyl638 CH.sub.3 4-iso-Propylphenyl639 CH.sub.3 2,4-Di-iso-Propylphenyl640 CH.sub.3 3,5-Di-iso-Propylphenyl641 CH.sub.3 4-n-Butylphenyl642 CH.sub.3 4-sec.-Butylphenyl643 CH.sub.3 4-iso-Butylphenyl644 CH.sub.3 4-tert.-Butylphenyl645 CH.sub.3 3-tert.-Butylphenyl646 CH.sub.3 2-tert.-Butylphenyl647 CH.sub.3 2,4-Di-tert.-Butylphenyl648 CH.sub.3 3,5-Di-tert.-Butylphenyl649 CH.sub.3 4-n-Hexylphenyl650 CH.sub.3 4-n-Dodecylphenyl651 CH.sub.3 2-Methyl-4-tert.-Butylphenyl652 CH.sub.3 2-Methyl-6-tert.-Butylphenyl653 CH.sub.3 2-Methyl-4-iso-Propylphenyl654 CH.sub.3 2-Methyl-4-Cyclohexylphenyl655 CH.sub.3 2-Methyl-4-Phenylphenyl656 CH.sub.3 2-Methyl-4-Benzylphenyl657 CH.sub.3 2-Methyl-4-Phenoxyphenyl658 CH.sub.3 2-Methyl-4-Benzyloxyphenyl659 CH.sub.3 2-Methyl-3-Chlorophenyl660 CH.sub.3 2-Methyl-4-Chlorophenyl661 CH.sub.3 2-Methyl-5-Chlorophenyl662 CH.sub.3 2-Methyl-6-Chlorophenyl663 CH.sub.3 2-Methyl-4-Fluorophenyl664 CH.sub.3 2-Methyl-3-Bromophenyl665 CH.sub.3 2-Methyl-4-Bromophenyl666 CH.sub.3 2-Methyl-3-Methoxyphenyl667 CH.sub.3 2-Methyl-4-Methoxyphenyl668 CH.sub.3 2-Methyl-5-Methoxyphenyl669 CH.sub.3 2-Methyl-6-Methoxyphenyl670 CH.sub.3 2-Methyl-4-iso-Propoxyphenyl671 CH.sub.3 2-Methyl-2,5-Dimethoxyphenyl672 CH.sub.3 2-Methoxyphenyl673 CH.sub.3 3-Methoxyphenyl oil; IR (film): 1708, 1634, 1285, 1256, 1129, 1111674 CH.sub.3 4-Methoxyphenyl oil; IR (film): 1708, 1253, 1129675 CH.sub.3 2,3-Dimethoxyphenyl676 CH.sub.3 2,4-Dimethoxyphenyl677 CH.sub.3 2,5-Dimethoxyphenyl678 CH.sub.3 2,6-Dimethoxyphenyl679 CH.sub.3 3,4-Dimethoxyphenyl680 CH.sub.3 3,5-Dimethoxyphenyl681 CH.sub.3 3,6-Dimethoxyphenyl682 CH.sub.3 2,3,4-Trimethoxyphenyl683 CH.sub.3 2,3,5-Trimethoxyphenyl684 CH.sub.3 2,3,6-Trimethoxyphenyl685 CH.sub.3 2,4,5-Trimethoxyphenyl686 CH.sub.3 2,4,6-Trimethoxyphenyl687 CH.sub.3 3,4,5-Trimethoxyphenyl688 CH.sub.3 2-Ethoxyphenyl689 CH.sub.3 3-Ethoxyphenyl690 CH.sub.3 4-Ethoxyphenyl691 CH.sub.3 2-iso-Propoxyphenyl692 CH.sub.3 3-iso-Propoxyphenyl693 CH.sub.3 4-iso-Propoxyphenyl694 CH.sub.3 3-tert.-Butoxyphenyl695 CH.sub.3 4-tert.-Butoxyphenyl696 CH.sub.3 2-Trifluoromethoxyphenyl697 CH.sub.3 3-Trifluoromethoxyphenyl698 CH.sub.3 4-Trifluoromethoxyphenyl699 CH.sub.3 3-(1',1',2',2'-Tetrafluoro)ethoxyphenyl700 CH.sub.3 4-(1',1',2',2'-Tetrafluoro)ethoxyphenyl701 CH.sub.3 2-Chloromethylphenyl702 CH.sub.3 3-Chloromethylphenyl703 CH.sub.3 4-Chloromethylphenyl704 CH.sub.3 2-Trifluoromethylphenyl oil; IR (film): 1705, 1634, 1313, 1130, 1107, 767705 CH.sub.3 3-Trifluoromethylphenyl oil; IR (film): 1710, 1635, 1276, 1128706 CH.sub.3 4-Trifluoromethylphenyl m.p.: 104-5.degree. C.; IR (KBr): 1697, 1628, 1323, 1123707 CH.sub.3 2-(Methoxyiminomethyl)phenyl708 CH.sub.3 3-(Methoxyiminomethyl)phenyl709 CH.sub.3 4-(Methoxyiminomethyl)phenyl710 CH.sub.3 2-(Ethoxyiminomethyl)phenyl711 CH.sub.3 3-(Ethoxyiminomethyl)phenyl712 CH.sub.3 4-(Ethoxyiminomethyl)phenyl713 CH.sub.3 2-(n-Propoxyiminomethyl)phenyl714 CH.sub.3 3-(n-Propoxyiminomethyl)phenyl715 CH.sub.3 4-(n-Propoxyiminomethyl)phenyl716 CH.sub.3 2-(iso-Propoxyiminomethyl)phenyl717 CH.sub.3 3-(iso-Propoxyiminomethyl)phenyl718 CH.sub.3 4-(iso-Propoxyiminomethyl)phenyl719 CH.sub.3 2-(n-Butoxyiminomethyl)phenyl720 CH.sub.3 3-(n-Butoxyiminomethyl)phenyl721 CH.sub.3 4-(n-Butoxyiminomethyl)phenyl722 CH.sub.3 2-(iso-Butoxyiminomethyl)phenyl723 CH.sub.3 3-(iso-Butoxyiminomethyl)phenyl724 CH.sub.3 4-(iso-Butoxyiminomethyl)phenyl725 CH.sub.3 2-(tert.-Butoxyiminomethyl)phenyl726 CH.sub.3 3-(tert.-Butoxyiminomethyl)phenyl727 CH.sub.3 4-(tert.-Butoxyiminomethyl)phenyl728 CH.sub.3 2-(n-Pentoxyiminomethyl)phenyl729 CH.sub.3 3-(n-Pentoxyiminomethyl)phenyl730 CH.sub.3 4-(n-Pentoxyiminomethyl)phenyl731 CH.sub.3 2-(n-Hexoxyiminomethyl)phenyl732 CH.sub.3 3-(n-Hexoxyiminomethyl)phenyl733 CH.sub.3 4-(n-Hexoxyiminomethyl)phenyl734 CH.sub.3 2-(Allyloxyiminomethyl)phenyl735 CH.sub.3 3-(Allyloxyiminomethyl)phenyl736 CH.sub.3 4-(Allyloxyiminomethyl)phenyl737 CH.sub.3 2-(Benzyloxyiminomethyl)phenyl738 CH.sub.3 3-(Benzyloxyiminomethyl)phenyl739 CH.sub.3 4-(Benzyloxyiminomethyl)phenyl740 CH.sub.3 2-(Methoxyimino-1'-ethyl)phenyl741 CH.sub.3 3-(Methoxyimino-1'-ethyl)phenyl742 CH.sub.3 4-(Methoxyimino-1'-ethyl)phenyl743 CH.sub.3 2-(Ethoxyimino-1'-ethyl)phenyl744 CH.sub.3 3-(Ethoxyimino-1'-ethyl)phenyl745 CH.sub.3 4-(Ethoxyimino-1'-ethyl)phenyl746 CH.sub.3 2-(n-Propoxyimino-1'-ethyl)phenyl747 CH.sub.3 3-(n-Propoxyimino-1'-ethyl)phenyl748 CH.sub.3 4-(n-Propoxyimino-1'-ethyl)phenyl749 CH.sub.3 2-(n-Butoxyamino-1'-ethyl)phenyl750 CH.sub.3 3-(n-Butoxyamino-1'-ethyl)phenyl751 CH.sub.3 4-(n-Butoxyamino-1'-ethyl)phenyl752 CH.sub.3 2-(n-Pentoxyimino-1'-ethyl)phenyl753 CH.sub.3 3-(n-Pentoxyimino-1'-ethyl)phenyl754 CH.sub.3 4-(n-Pentoxyimino-1'-ethyl)phenyl755 CH.sub.3 2-(n-Hexoxyimino-1'-ethyl)phenyl756 CH.sub.3 3-(n-Hexoxyimino-1'-ethyl)phenyl757 CH.sub.3 4-(n-Hexoxyimino-1'-ethyl)phenyl758 CH.sub.3 2-(Allyloxyimino-1'-ethyl)phenyl759 CH.sub.3 3-(Allyloxyimino-1'-ethyl)phenyl760 CH.sub.3 4-(Allyloxyimino-1'-ethyl)phenyl761 CH.sub.3 2-(Benzyloxyimino-1'-ethyl)phenyl762 CH.sub.3 3-(Benzyloxyimino-1'-ethyl)phenyl763 CH.sub.3 4-(Benzyloxyimino-1'-ethyl)phenyl764 CH.sub.3 2-Phenylphenyl765 CH.sub.3 3-Phenylphenyl766 CH.sub.3 4-Phenylphenyl767 CH.sub.3 2-Phenoxyphenyl768 CH.sub.3 3-Phenoxyphenyl769 CH.sub.3 4-Phenoxyphenyl oil; IR (film): 1708, 1489, 1240, 1129770 CH.sub.3 2-Benzyloxyphenyl771 CH.sub.3 3-Benzyloxyphenyl772 CH.sub.3 4-Benzyloxyphenyl773 CH.sub.3 4-(Imidazol-1'-yl)phenyl774 CH.sub.3 4-(Piperazin-1'-yl)phenyl775 CH.sub.3 4-(Morpholin-1'-yl)phenyl776 CH.sub.3 4-(Piperidin-1'-yl)phenyl777 CH.sub.3 4-(Pyridyl-2'-oxy)phenyl778 CH.sub.3 2-Cyclopropylphenyl779 CH.sub.3 3-Cyclopropylphenyl780 CH.sub.3 4-Cyclopropylphenyl781 CH.sub.3 3-Cyclohexylphenyl782 CH.sub.3 4-Cyclohexylphenyl783 CH.sub.3 4-Oxiranylphenyl784 CH.sub.3 4-(1',3'-Dioxan-2'-yl)phenyl785 CH.sub.3 4-(Tetrahydropyran-2-yloxy)phenyl786 CH.sub.3 1-Naphthyl787 CH.sub.3 2-Naphthyl788 CH.sub.3 9-Anthryl789 CH.sub.3 1-Naphthoxy790 CH.sub.3 2-Naphthoxy791 CH.sub.3 9-Anthroxy792 CH.sub.3 Phenoxy793 CH.sub.3 2-Chlorophenoxy794 CH.sub.3 3-Chlorophenoxy795 CH.sub.3 4-Chlorophenoxy796 CH.sub.3 4-Methylphenoxy797 CH.sub.3 4-tert.-Butylphenoxy798 CH.sub.3 4-Methoxyphenoxy799 CH.sub.3 4-Ethoxyphenoxy800 CH.sub.3 4-tert.-Butoxyphenoxy801 CH.sub.3 Phenylthio862 CH.sub.3 2-Chlorophenylthio803 CH.sub.3 4-Chlorophenylthio804 CH.sub.3 Benzyl805 CH.sub.3 2-Methylbenzyl806 CH.sub.3 3-Methylbenzyl807 CH.sub.3 4-Methylbenyzl808 CH.sub.3 4-tert.-Butylbenzyl809 CH.sub.3 2-Chlorobenzyl810 CH.sub.3 3-Chlorobenzyl811 CH.sub.3 4-Chlorobenzyl812 CH.sub.3 2,4-Dichlorobenzyl813 CH.sub.3 2,6-Dichlorobenzyl814 CH.sub.3 2,4,6-Trichlorobenzyl815 CH.sub.3 2-Trifluoromethylbenzyl816 CH.sub.3 3-Trifluoromethylbenzyl817 CH.sub.3 4-Trifluoromethylbenzyl818 CH.sub.3 2-Methoxybenzyl819 CH.sub.3 4-Methoxybenzyl820 CH.sub.3 4-tert.-Butoxybenzyl821 CH.sub.3 4-Phenoxybenzyl822 CH.sub.3 1-Phenethyl823 CH.sub.3 2-Phenethyl824 CH.sub.3 1-Phenylpropyl825 CH.sub.3 2-Phenylpropyl826 CH.sub.3 3-Phenylpropyl827 CH.sub.3 2-Methyl-2-phenylpropyl828 CH.sub.3 2-Methyl-3-phenylpropyl829 CH.sub.3 4-Phenylbutyl830 CH.sub.3 2-Phenyl-1-ethenyl831 CH.sub.3 1-Phenyl-l-ethenyl832 CH.sub.3 1-Phenyl-1-propenyl833 CH.sub.3 1-Phenyl-1-propen-2-yl834 CH.sub.3 2,2-Diphenylethenyl835 CH.sub.3 Phenoxymethyl836 CH.sub.3 2-Pyridyl837 CH.sub.3 3-Pyridyl838 CH.sub.3 4-Pyridyl839 CH.sub.3 2,6-Pyrimidinyl840 CH.sub.3 1,5-Pyrimidinyl841 CH.sub.3 2-Thienyl842 CH.sub.3 3-Thienyl843 CH.sub.3 2-Furyl844 CH.sub.3 3-Furyl845 CH.sub.3 1-Pyrrolyl846 CH.sub.3 1-Imidazolyl847 CH.sub.3 1,2,4-Triazolyl848 CH.sub.3 1,3,4-Triazolyl849 CH.sub.3 4-Thiazolyl850 CH.sub.3 2-Benzothiazolyl851 CH.sub.3 2-Pyridyloxy852 CH.sub.3 2-Pyrimidinyloxy853 CH.sub.3 2-Pyridylthio854 CH.sub.3 2-Pyrimidinylthio855 CH.sub.3 2-Benzothiazolylthio856 CH.sub.3 Phenylthiomethyl857 CH.sub.3 2-Pyridylmethyl858 CH.sub.3 3-Pyridylmethyl859 CH.sub.3 Furfuryloxy860 CH.sub.3 Thienylmethoxy861 CH.sub.3 3-Isoxazolylmethoxy862 CH.sub.3 2-Oxazolylmethoxy863 CH.sub.3 2-Pyridylmethoxy864 CH.sub.3 2'-Furyl-2-ethenyl865 CH.sub.3 2'-Thienyl-2-ethenyl866 CH.sub.3 3'-Pyridyl-2-ethenyl867 CH.sub.3 Oxiranyl868 CH.sub.3 1-Aziridinyl869 CH.sub.3 1-Azetidinyl870 CH.sub.3 1-Pyrrolidinyl871 CH.sub.3 2-Tetrahydrofuryl872 CH.sub.3 2-Tetrahydropyranyl873 CH.sub.3 3-Tetrahydropyranyl874 CH.sub.3 1-Piperidinyl875 CH.sub.3 1-Morpholinyl076 CH.sub.3 1-Piperazinyl877 CH.sub.3 1,3-Dioxan-2-yl878 CH.sub.3 3-Tetrahydrothiopyranyl879 CH.sub.3 2-Dihydropyranyloxy880 CH.sub.3 2-Tetrahydropyranyloxy881 CH.sub.3 CF.sub.3882 CH.sub.3 2-Fluoroethyl883 CH.sub.3 2,2,2-Trifluoroethyl884 CH.sub.3 Pentafluoroethyl885 CH.sub.3 Chloromethyl886 CH.sub.3 Dichloromethyl887 CH.sub.3 Trichloromethyl888 CH.sub.3 2-Chloroethyl889 CH.sub.3 2,2,2-Trichloroethyl890 CH.sub.3 Pentachloroethyl891 CH.sub.3 Cyclopropyl892 CH.sub.3 Cyclobutyl893 CH.sub.3 Cyclopentyl894 CH.sub.3 Cyclohexyl895 CH.sub.3 1-Methylcyclopropyl896 CH.sub.3 2,2-Dimethylcyclopropyl897 CH.sub.3 1-Methylcyclohexyl898 CH.sub.3 2,2-Difluorocyclopropyl899 CH.sub.3 2,2-Dichlorocyclopropyl900 CH.sub.3 2,2-Dibromocyclopropyl901 CH.sub.3 2,2-Dichloro-3-methylcyclopropyl902 CH.sub.3 2,2,3,3-Tetrafluorocyclobutyl903 CH.sub.3 Ethenyl904 CH.sub.3 1-Propenyl905 CH.sub.3 2-Methyl-1-propenyl906 CH.sub.3 4-Methylpent-3-en-1-yl907 CH.sub.3 2-Propenyl908 CH.sub.3 2-Butenyl909 CH.sub.3 1-Methyl-2-propenyl910 CH.sub.3 3-Methyl-2-butenyl911 CH.sub.3 2,2-Difluoroethenyl912 CH.sub.3 2,2-Dichloroethenyl913 CH.sub.3 3,3,3-Trifluoropropenyl914 CH.sub.3 3,3,3-Trichloropropenyl915 CH.sub.3 3-Chloro-2-propenyl916 CH.sub.3 Cyclopent-1-enyl917 CH.sub.3 Cyclopentadienyl918 CH.sub.3 Cyclohex-1-enyl919 CH.sub.3 Pentafluorocyclopentadienyl920 CH.sub.3 Pentachlorocyclopentadienyl921 Phenyl Phenyl922 Phenyl 2-Fluorophenyl923 Phenyl 4-Fluorophenyl924 Phenyl 2-Chlorophenyl925 Phenyl 3-Chlorophenyl926 Phenyl 4-Chlorophenyl927 Phenyl 3,4-Dichlorophenyl928 Phenyl 4-Nitrophenyl929 Phenyl 2-CF.sub.3 -Phenyl930 Phenyl 3-CF.sub.3 -Phenyl931 Phenyl 4-CF.sub.3 -Phenyl932 Phenyl 2-Methylphenyl933 Phenyl 3-Methylphenyl934 Phenyl 4-Methylphenyl935 Phenyl 2,4-Dimethylphenyl936 Phenyl 4-tert.-Butylphenyl937 Phenyl 4-Methoxyphenyl938 4-Fluorophenyl 4-Fluorophenyl939 2-Fluorophenyl 4-Fluorophenyl940 2-Chlorophenyl 4-Fluorophenyl941 2-Chlorophenyl 2-Chlorophenyl942 3-Chlorophenyl 3-Chlorophenyl943 4-Chlorophenyl 4-Chlorophenyl944 2-Chlorophenyl 4-Chlorophenyl945 4-Methoxyphenyl 4-Methoxyphenyl946 4-Dimethylaminophenyl 4-Dimethylaminophenyl947 Phenyl Naphthyl948 Ethyl Ethyl949 Ethyl n-Propyl950 Ethyl iso-Propyl951 Ethyl n-Butyl952 Ethyl iso-Butyl953 Ethyl 2-Methyl-butyl954 Ethyl Benzyl955 n-Propyl n-Propyl956 iso-Propyl iso-Propyl957 n-Butyl n-Butyl958 iso-Butyl iso-Butyl959 tert.-Butyl tert.-Butyl960 Benzyl Benzyl961 Pentachloroethyl Pentachloroethyl962 n-Hexyl n-Hexyl963 Ethoxycarbonyl Ethoxycarbonyl964 Phenyl Benzoyl965 Ethyl Phenyl966 n-Butyl Phenyl967 Styryl Styryl968 2-Pyridyl 2-Pyridyl969 3-Pyridyl 3-Pyridyl970 CH.sub.3 3,5-Dibenzyloxyphenyl IR (film): 1707, 1581, 1256, 1157, 1129__________________________________________________________________________
TABLE II______________________________________ ##STR20##No. R.sup.3 R.sup.4 Data______________________________________1 Cl Phenyl2 Cl Cyano3 Cl Ethoxycarbonyl4 Cl Cyclopropyl5 CF.sub.3 CF.sub.36 CF.sub.3 Phenyl7 CCl.sub.3 CCl.sub.38 CCl.sub.3 Phenyl9 CH.sub.2 Cl Phenyl10 CF.sub.2 CF.sub.3 Phenyl11 CF.sub.2 Cl Phenyl12 CHCl.sub.2 Phenyl13 Cyclo- Cyclopropyl propyl14 Cyclo- Phenyl oil; IR (film): propyl 1437 1321, 1219, 1045, 983, 76615 Cyclo- 4-Fluorophenyl oil; IR (film): propyl 1508, 1321, 1222, 1046, 985, 83916 Cyclo- 4-Chlorophenyl oil; IR (film): propyl 1489, 1321, 1218, 1090, 1046, 82917 Cyclo- 4-Methoxyphenyl oil; IR (film): propyl 1300, 1250, 1218, 983, 83318 Cyclo- 4-Ethoxyphenyl propyl19 Cyclo- 4-Phenoxyphenyl propyl20 Cyclo- Pentachlorophenyl propyl21 Cyclo- Pentafluorophenyl propyl22 Cyclo- Phenyl pentyl23 Cyclo- Phenyl hexyl24 Phenyl 2,2-Dichloro-1-methyl- cyclopropyl25 Phenyl 2,2-Difluorocyclo- propyl26 Phenyl 2,2-Dichlorocyclo- propyl27 Phenyl 2,2-Dibromocyclo- propyl28 Phenyl 2,2,3,3-Tetrafluoro- cyclobutyl29 Phenyl 2,2-Dimethylcyclo- propyl30 Phenyl 1-Methylcyclohexyl31 CN Methoxymethyl32 CN Ethoxymethyl33 CN n-Propoxymethyl34 CN iso-Propoxymethyl35 CN tert.-Butoxymethyl36 CN 2-Methoxyprop-2-yl m.p.: 83.degree. C.; IR (KBr): 1437, 1223, 1206, 1069, 100637 CN 2-Ethoxyprop-2-yl oil; IR (film): 1439, 3122, 1221, 1202, 104838 CN 2-n-Propoxyprop-2-yl oil; IR (film): 1438, 1322, 1221, 1203, 104839 CN 2-iso-Propoxyprop-2-yl m.p.: 74-5.degree. C. IR (KBr): 1302, 1231, 1169, 1108, 1079, 997, 75740 CN 2-tert.-Butoxyprop-2-yl41 CN Methylthiomethyl42 CN tert.-Butylthiomethyl43 CN 2-Methylthioprop-2-yl m.p.: 107.degree. C.; IR (KBr): 1434, 1297, 1126, 1066, 1010, 76944 CN 2-iso-Propylthioprop- oil; IR (film): 2-yl 1438, 1366, 1321, 1221, 120245 CN 2-tert.-Butylthioprop- 2-yl46 CN Methyl47 CN Ethyl48 CN n-Propyl49 CN iso-Propyl oil; IR (film): 1439, 1321, 1222, 1012, 76750 CN n-Butyl51 CN iso-Butyl52 CN sec.-Butyl53 CN tert.-Butyl54 CN n-Hexyl55 CN n-Decyl56 CN Cyclopropyl m.p.: 74-75.degree. C.; IR (KBr): 1433, 1223, 1043, 76357 CN Cyclohexyl58 CN Phenylthiomethyl59 CN 2-Phenylthiomethyl60 CN 2-(2'-Chlorophenyl- thio)prop-2-yl61 CN Ethynyl62 CN 1-Propynyl63 CN Methoxy64 CN Ethoxy65 CN n-Propoxy66 CN lso-Propoxy67 CN n-Butoxy68 CN iso-Butoxy69 CN sec.-Butoxy70 CN tert.-Butoxy71 CN Methylthio72 CN Ethylthio73 CN n-Propylthio74 CN iso-Propylthio75 CN n-Butylthio76 CN iso-Butylthio77 CN sec.-Butylthio78 CN tert.-Butylthio79 CN Benzylthio80 CN Trifluoromethoxy81 CN Cyano82 CN Amino83 CN Methylamino84 CN Dimethylamino85 CN Ethylamino86 CN Diethylamino87 CN Di-n-Propylamino88 CN Di-iso-Propylamino89 CN Di-n-Butylamino90 CN Di-iso-Butylamino91 CN Acetyl92 CN Propion-1-yl93 CN Butyr-1-yl94 CN iso-Butyr-1-yl95 CN Pivaloyl96 CN Benzoyl97 CN 4-Chlorobenzoyl98 CN Benzylcarbonyl99 CN Methoxycarbonyl100 CN Ethoxycarbonyl101 CN n-Propoxycarbonyl102 CN iso-Propoxycarbonyl103 CN n-Butoxycarbonyl104 CN iso-Butoxycarbonyl105 CN sec.-Butoxycarbonyl106 CN tert.-Butoxycarbonyl107 CN n-Hexoxycarbonyl108 CN Phenoxycarbonyl109 CN 4-Chlorophenoxy- carbonyl110 CN Benzyloxycarbonyl111 CN Aminocarbonyl112 CN Dimethylamino- carbonyl113 CN Diethylaminocarbonyl114 CN Di-iso-Propylamino- carbonyl115 CN Phenylaminocarbonyl116 CN N-Methyl-N-Phenyl- aminocarbonyl117 CN Phenyl m.p.: 99-100.degree. C.; IR (KBr): 1436, 1215, 1208, 1097, 1026, 944, 766, 690118 CN 2-Fluorophenyl119 CN 3-Fluorophenyl120 CN 4-Fluorophenyl121 CN Pentafluorophenyl122 CN 2-Chlorophenyl123 CN 3-Chlorophenyl124 CN 4-Chlorophenyl125 CN Pentachlorophenyl126 CN 2,3-Dichlorophenyl127 CN 2,4-Dichlorophenyl128 CN 2,5-Dichlorophenyl129 CN 2,6-Dichlorophenyl130 CN 3,4-Dichlorophenyl131 CN 3,5-Dichlorophenyl132 CN 2,3,4-Trichlorophenyl133 CN 2,3,5-Trichlorophenyl134 CN 2,3,6-Trichlorophenyl135 CN 2,4,5-Trichlorophenyl136 CN 2,4,6-Trichlorophenyl137 CN 3,4,5-Trichlorophenyl138 CN 2,3,4,6-Tetrachloro- phenyl139 CN 2,3,5-6-Tetrachloro- phenyl140 CN 2-Bromophenyl141 CN 3-Bromophenyl142 CN 4-Bromophenyl143 CN 2,4-Dibromophenyl144 CN 3-Bromo-4-fluoro- phenyl145 CN 3-Bromo-4-methoxy- phenyl146 CN 2-Iodophenyl147 CN 3-Iodophenyl148 CN 4-Iodophenyl149 CN 2-Chloro-4-fluorophenyl150 CN 2-Chloro-5-fluorophenyl151 CN 2-Chloro-6-fluorophenyl152 CN 2-Chloro-4-bromophenyl153 CN 2-Bromo-4-chlorophenyl154 CN 2-Bromo-4-fluorophenyl155 CN 3-Bromo-4-chlorophenyl156 CN 3-Chloro-4-fluorophenyl157 CN 3-Fluoro-4-chlorophenyl158 CN 2-Cyanophenyl159 CN 3-Cyanophenyl160 CN 4-Cyanophenyl161 CN 2-Nitrophenyl162 CN 3-Nitrophenyl163 CN 4-Nitrophenyl164 CN 2-Methylphenyl165 CN 3-Methylphenyl166 CN 4-Methylphenyl167 CN 2,4-Dimethylphenyl168 CN 2,6-Dimethylphenyl169 CN 3,4-Dimethylphenyl170 CN 3,5-Dimethylphenyl171 CN 2,3,4-Trimethylphenyl172 CN 2,3,5-Trimethylphenyl173 CN 2,3,6-Trimethylphenyl174 CN 2,4,5-Trimethylphenyl175 CN 2,4,6-Trimethylphenyl176 CN 3,4,5-Trimethylphenyl177 CN Pentamethylphenyl178 CN 2-Ethylphenyl179 CN 3-Ethylphenyl180 CN 4-Ethylphenyl181 CN 3,5-Diethylphenyl182 CN 2-n-Propylphenyl183 CN 3-n-Propylphenyl184 CN 4-n-Propylphenyl185 CN 2-iso-Propylphenyl186 CN 3-iso-Propylphenyl187 CN 4-iso-Propylphenyl188 CN 2,4-Di-lso-Propyl- phenyl189 CN 3,5-Di-iso-Propyl- phenyl190 CN 4-n-Butylphenyl191 CN 4-sec.-Butylphenyl192 CN 4-iso-Butylphenyl193 CN 4-tert.-Butylphenyl194 CN 3-tert.-Butylphenyl195 CN 2-tert.-Butylphenyl196 CN 2,4-Di-tert.-Butylphenyl197 CN 3,5-Di-tert.-Butylphenyl198 CN 4-n-Hexylphenyl199 CN 4-n-Dodecylphenyl200 CN 2-Methyl-4-tert.-Butyl- phenyl201 CN 2-Methyl-6-tert.-Butyl- phenyl202 CN 2-Methyl-4-iso-Propyl- phenyl203 CN 2-Methyl-4-Cyclo- hexylphenyl204 CN 2-Methyl-4-Phenyl- phenyl205 CN 2-methyl-4-Benzyl- phenyl206 CN 2-Methyl-4-Phenoxy- phenyl207 CN 2-Methyl-4-Benzyloxy- phenyl208 CN 2-Methyl-3-Chloro- phenyl209 CN 2-Methyl-4-Chloro- phenyl210 CN 2-Methyl-5-Chloro- phenyl211 CN 2-Methyl-6-Chloro- phenyl212 CN 2-Methyl-4-Fluoro- phenyl213 CN 2-methyl-3-Bromo- phenyl214 CN 2-Methyl-4-Bromo- phenyl215 CN 2-methyl-3-Methoxy- phenyl216 CN 2-Methyl-4-Methoxy- phenyl217 CN 2-Methyl-5-Methoxy- phenyl218 CN 2-Methyl-6-Methoxy- phenyl219 CN 2-Methyl-4-iso- Propoxyphenyl220 CN 2-Methyl-2,5- Dimethoxyphenyl221 CN 2-Methoxyphenyl222 CN 3-Methoxyphenyl223 CN 4-Methoxyphenyl224 CN 2,3-Dimethoxyphenyl225 CN 2,4-Dimethoxyphenyl226 CN 2,5-Dimethoxyphenyl227 CN 2,6-Dimethoxyphenyl228 CN 3,4-Dimethoxyphenyl229 CN 3,5-Dimethoxyphenyl230 CN 3,6-Dimethoxyphenyl231 CN 2,3,4-Trimethoxyphenyl232 CN 2,3,5-Trimethoxyphenyl233 CN 2,3,6-Trimethoxyphenyl234 CN 2,4,5-Trimethoxyphenyl235 CN 2,4,6-Trimethoxyphenyl236 CN 3,4,5-Trimethoxyphenyl237 CN 2-Ethoxyphenyl238 CN 3-Ethoxyphenyl239 CN 4-Ethoxyphenyl240 CN 2-iso-Propoxyphenyl241 CN 3-iso-Propoxyphenyl242 CN 4-iso-Propoxyphenyl243 CN 3-tert.-Butoxyphenyl244 CN 4-tert.-Butoxyphenyl245 CN 2-Trifluoromethoxy- phenyl246 CN 3-Trifluoromethoxy- phenyl247 CN 4-Trifluoromethoxy- phenyl248 CN 3-(1',1',2',2'-Tetra- fluoro)ethoxyphenyl249 CN 4-(1',1',2',2'-Tetra- fluoro)ethoxyphenyl250 CN 2-Chloromethylphenyl251 CN 3-Chloromethylphenyl252 CN 4-Chloromethylphenyl253 CN 2-Trifluoromethylphenyl254 CN 3-Trifluoromethylphenyl255 CN 4-Trifluoromethylphenyl256 CN 2-(Methoxyimino- methyl)phenyl257 CN 3-(Methoxyimino- methyl)phenyl258 CN 4-(Methoxyimino- methyl)phenyl259 CN 2-(Ethoxyimino- methyl)phenyl260 CN 3-(Ethoxyimino- methyl)phenyl261 CN 4-(Ethoxyimino- methyl)phenyl262 CN 2-(n-Propoxyimino- methyl)phenyl263 CN 3-(n-Propoxyimino methyl)phenyl264 CN 4-(n-Propoxyimino- methyl)phenyl265 CN 2-(iso-Propoxyimino- methyl)phenyl266 CN 3-(iso-Propoxyimino- methyl)phenyl267 CN 4-(iso-Propoxyimino- methyl)phenyl268 CN 2-(n-Butoxyimino- methyl)phenyl269 CN 3-(n-Butoxyimino- methyl)phenyl270 CN 4-(n-Butoxyimino- methyl)phenyl271 CN 2-(iso-Butoxyimino- methyl)phenyl272 CN 3-(iso-Butoxyimino- methyl)phenyl273 CN 4-(iso-Butoxyimino- methyl)phenyl274 CN 2-(tert.-Butoxyimino- methyl)phenyl275 CN 3-(tert.-Butoxyimino- methyl)phenyl276 CN 4-(tert.-Butoxyimino- methyl)phenyl277 CN 2-(n-Pentoxyimino- methyl)phenyl278 CN 3-(n-Pentoxyimino- methyl)phenyl279 CN 4-(n-Pentoxyimino- methyl)phenyl280 CN 2-(n-Hexoxyimino- methyl)phenyl281 CN 3-(n-Hexoxyimino- methyl)phenyl282 CN 4-(n-Hexoxyimino- methyl)phenyl283 CH 2-(Allyloxyimino- methyl)phenyl284 CN 3-(Allyloxyimino- methyl)phenyl285 CN 4-(Allyloxyimino- methyl)phenyl286 CH 2-(Benzyloxyimino- methyl)phenyl287 CN 3-(Benzyloxyimino- methyl)phenyl288 CN 4-(Benzyloxyimino- methyl)phenyl289 CN 2-(Methoxyimino-1'- ethyl)phenyl290 CN 3-(Methoxyimino-1'- ethyl)phenyl291 CN 4-(Methoxyimino-1'- ethyl)phenyl292 CN 2-(Ethoxyimino-1'- ethyl)phenyl293 CN 3-(Ethoxyimino-1'- ethyl)phenyl294 CN 4-(Ethoxyimino-1'- ethyl)phenyl295 CN 2-(n-Propoxyimino-1'- ethyl)phenyl296 CN 3-(n-Propoxyimino-1'- ethyl)phenyl297 CN 4-(n-Propoxyimino-1'- ethyl)phenyl298 CN 2-(n-Butoxyamino-1'- ethyl)phenyl299 CN 3-(n-Butoxyamino-1'- ethyl)phenyl300 CN 4-(n-Butoxyamino-1'- ethyl)phenyl301 CN 2-(n-Pentoxyimino-1'- ethyl)phenyl302 CN 3-(n-Pentoxyimino-1'- ethyl)phenyl303 CN 4-(n-Pentoxyimino-1'- ethyl)phenyl304 CN 2-(n-Hexoxyimino-1'- ethyl)phenyl305 CN 3-(n-Hexoxyimino-1'- ethyl)phenyl306 CN 4-(n-Hexoxyimino-1'- ethyl)phenyl307 CN 2-(Allyloxyimino-1'- ethyl)phenyl308 CN 3-(Allyloxyimino-1'- ethyl)phenyl309 CN 4-(Allyloxyimino-1'- ethyl)phenyl310 CN 2-(Benzyloxyimino-1'- ethyl)phenyl311 CN 3-(Benzyloxyimino-1'- ethyl)phenyl312 CN 4-(Benzyloxyimino-1'- ethyl)phenyl313 CN 2-Phenylphenyl314 CN 3-Phenylphenyl315 CN 4-Phenylphenyl316 CN 2-Phenoxyphenyl317 CN 3-Phenoxyphenyl318 CN 4-Phenoxyphenyl319 CN 2-Benzyloxyphenyl320 CN 3-Benzyloxyphenyl321 CN 4-Benzyloxyphenyl322 CN 4-(imidazol-1'- yl)phenyl323 CN 4-(Piperazin-1'- yl)phenyl324 CN 4-(Morpholin-1'- yl)phenyl325 CN 4-(Piperidin-1'- yl)phenyl326 CN 4-(Pyridyl-2'- oxy)phenyl327 CN 2-Cyclopropylphenyl328 CN 3-Cyclopropylphenyl329 CN 4-Cyclopropylphenyl330 CN 3-Cyclohexylphenyl331 CN 4-Cyclohexylphenyl332 CN 4-Oxiranylphenyl333 CN 4-(1',3'-Dioxan-2'- yl)phenyl334 CN 4-(Tetrahydropyran-2- yloxy)phenyl335 CN 1-Naphthyl336 CN 2-Naphthyl337 CN 9-Anthryl338 CN 1-Naphthoxy339 CN 2-Naphthoxy340 CN 9-Anthroxy341 CN Phenoxy342 CN 2-Chlorophenoxy343 CN 3-Chlorophenoxy344 CN 4-Chlorophenoxy345 CN 4-Methylphenoxy346 CN 4-tert.-Butylphenoxy347 CN 4-Methoxyphenoxy348 CN 4-Ethoxyphenoxy349 CN 4-tert.-Butoxyphenoxy350 CN Phenylthio351 CN 2-Chlorophenylthio352 CN 4-Chlorophenylthio353 CN Benzyl354 CN 2-Methylbenzyl355 CN 3-Methylbenzyl356 CN 4-Methylbenzyl357 CN 4-tert.-Butylbenzyl358 CN 2-Chlorobenzyl359 CN 3-Chlorobenzyl360 CN 4-Chlorobenzyl361 CN 2,4-Dichlorobenzyl362 CN 2,6-Dichlorobenzyl363 CN 2,4,6-Trichlorobenzyl364 CN 2-Trifluoromethyl- benzyl365 CN 3-Trifluoromethyl- benzyl366 CN 4-Trifluoromethyl- benzyl367 CN 2-Methoxybenzyl368 CN 4-Methoxybenzyl369 CN 4-tert.-Butoxybenzyl370 CN 4-Phenoxybenzyl371 CN 1-Phenethyl372 CN 2-Phenethyl373 CN 1-Phenylpropyl374 CN 2-Phenylpropyl375 CN 3-Phenylpropyl376 CN 2-Methyl-2-phenyl- propyl377 CN 2-Methyl-3-phenyl- propyl378 CN 4-Phenylbutyl379 CN 2-Phenyl-1-ethenyl380 CN 1-Phenyl-1-ethenyl381 CN 1-Phenyl-1-propenyl382 CN 1-Phenyl-1-propen-2-yl383 CN 2,2-Diphenylethenyl384 CN Phenoxymethyl385 CN 2-Pyridyl386 CN 3-Pyridyl387 CN 4-Pyridyl388 CN 2,6-Pyrimidinyl389 CN 1,5-Pyrimidinyl390 CN 2-Thienyl391 CN 3-Thienyl392 CN 2-Furyl393 CN 3-Furyl394 CN 1-Pyrrolyl395 CN 1-imidazolyl396 CN 1,2,4-Triazolyl397 CN 1,3,4-Triazolyl398 CN 4-Thiazolyl399 CN 2-Benzothiazolyl400 CN 2-Pyridyloxy401 CN 2-Pyrimidinyloxy402 CN 2-Pyridylthio403 CN 2-Pyrimidinylthio404 CN 2-Benzothiazolylthio405 CN Phenylthiomethyl406 CN 2-Pyridylmethyl407 CN 3-Pyridylmethyl408 CN Furfurytoxy409 CN Thienylmethoxy410 CN 3-Isoxazolylmethoxy411 CN 2-Oxazolylmethoxy412 CN 2-Pyridylmethoxy413 CN 2'-Furyl-2-ethenyl414 CN 2'-Thienyl-2-ethenyl415 CN 3'-Pyridyl-2-ethenyl416 CN Oxiranyl417 CN 1-Aziridinyl418 CN 1-Azetidinyl419 CN 1-Pyrrolidinyl420 CN 2-Tetrahydrofuryl421 CN 2-Tetrahydropyranyl422 CN 3-Tetrahydropyranyl423 CN 1-Piperidinyl424 CN 1-Morpholinyl425 CN 1-Piperazinyl426 CN 1,3-Dioxan-2-yl427 CN 3-Tetrahydrothiopyranyl428 CN 2-Dihydropyranyloxy429 CN 2-Tetrahydropyranyloxy oil; IR (film): 1439, 1228, 1209, 1050, 1025 767430 CN (CH.sub.2).sub.4431 CN (CH.sub.2).sub.5432 CN (CH.sub.2).sub.6433 CN434 CN435 CN ##STR21##436 CN ##STR22##437 CN ##STR23##438 CN ##STR24##439 CN ##STR25##440 CN ##STR26##441 CN CF.sub.3442 CN 2-Fluoroethyl443 CN 2,2,2-Trifluoroethyl444 CN Pentafluoroethyl445 CN Chloromethyl446 CN Dichloromethyl447 CN Trichloromethyl448 CN 2-Chloroethyl449 CN 2,2,2-Trichloroethyl450 CN Pentachloroethyl451 CN Cyclopropyl452 CN Cyclobutyl453 CN Cyclopentyl454 CN Cyclohexyl455 CN 1-Methylcyclopropyl456 CN 2,2-Dimethylcyclo- propyl457 CN 1-Methylcyclohexyl458 CN 2,2-Difluorocyclopropyl459 CN 2,2-Dichlorocyclopropyl460 CN 2,2-Dibromocyclopropyl461 CN 2,2-Dichloro-3- Methylcyclopropyl462 CN 2,2,3,3-Tetrafluoro- cyclobutyl463 CN Ethenyl464 CN 1-Propenyl465 CN 2-Methyl-1-propenyl466 CN 4-Methylpent-3-en-1-yl467 CN 2-Propenyl468 CN 2-Butenyl469 CN 1-Methyl-2-propenyl470 CN 3-Methyl-2-butenyl471 CN 2,2-Difluoroethenyl472 CN 2,2-Dichloroethenyl473 CN 3,3,3-Trifluoro- propenyl474 CN 3,3,3-Trichloro- propenyl475 CN 3-Chloro-2-propenyl476 CN Cyclopent-1-enyl477 CN Cyclopentadienyl478 CN Cyclohex-1-enyl479 CN Pentafluorocyclo- pentadienyl480 CN Pentachlorocyclo- pentadienyl481 CN Styryl482 CH.sub.3 Methoxymethyl483 CH.sub.3 Ethoxymethyl484 CH.sub.3 n-Propoxymethyl485 CH.sub.3 iso-Propoxymethyl486 CH.sub.3 tert.-Butoxymethyl487 CH.sub.3 2-Methoxyprop-2-yl488 CH.sub.3 2-Ethoxyprop-2-yl489 CH.sub.3 2-n-Propoxyprop-2-yl490 CH.sub.3 2-iso-Propoxyprop-2-yl491 CH.sub.3 2-tert.-Butoxyprop-2-yl492 CH.sub.3 Methylthiomethyl493 CH.sub.3 tert.-Butylthiomethyl494 CH.sub.3 2-Methylthioprop-2-yl495 CH.sub.3 2-iso-Propylthioprop-2- yl496 CH.sub.3 2-tert.-Butylthioprop-2- yl497 CH.sub.3 Methyl m.p. 68-71.degree. C.; IR (KBr): 1137, 1298, 1067, 1023, 1007, 771498 CH.sub.3 Ethyl499 CH.sub.3 n-Propyl500 CH.sub.3 iso-Propyl501 CH.sub.3 n-Butyl502 CH.sub.3 iso-Butyl503 CH.sub.3 sec.-Butyl504 CH.sub.3 tert.-Butyl505 CH.sub.3 n-Hexyl506 CH.sub.3 n-Decyl507 CH.sub.3 Cyclopropyl508 CH.sub.3 Cyclohexyl509 CH.sub.3 Phenylthiomethyl510 CH.sub.3 2-Phenylthiomethyl511 CH.sub.3 2-(2'-Chlorophenyl- thio)prop-2-yl512 CH.sub.3 Ethynyl513 CH.sub.3 1-Propynyl514 CH.sub.3 Methoxy515 CH.sub.3 Ethoxy516 CH.sub.3 n-Propoxy517 CH.sub.3 iso-Propoxy518 CH.sub.3 n-Butoxy519 CH.sub.3 iso-Butoxy520 CH.sub.3 sec.-Butoxy521 CH.sub.3 tert.-Butoxy522 CH.sub.3 Methylthio523 CH.sub.3 Ethylthio524 CH.sub.3 n-Propylthio525 CH.sub.3 iso-Propylthio526 CH.sub.3 n-Butylthio527 CH.sub.3 iso-Butylthio528 CH.sub.3 sec.-Butylthio529 CH.sub.3 tert.-Butylthio530 CH.sub.3 Benzylthio531 CH.sub.3 Trifluoromethoxy532 CH.sub.3 Cyano533 CH.sub.3 Amino534 CH.sub.3 Methylamino535 CH.sub.3 Dimethylamino536 CH.sub.3 Ethylamino537 CH.sub.3 Diethylamino538 CH.sub.3 Di-n-Propylamino539 CH.sub.3 Di-iso-Propylamino540 CH.sub.3 Di-n-Butylamino541 CH.sub.3 Di-iso-Butylamino542 CH.sub.3 Acetyl543 CH.sub.3 Propion-1-yl544 CH.sub.3 Butyr-1-yl545 CH.sub.3 iso-Butyr-1-yl546 CH.sub.3 Pivaloyl547 CH.sub.3 Benzoyl548 CH.sub.3 4-Chlorobenzoyl549 CH.sub.3 Benzylcarbonyl550 CH.sub.3 Methoxycarbonyl551 CH.sub.3 Ethoxycarbonyl552 CH.sub.3 n-Propoxycarbonyl553 CH.sub.3 iso-Propoxycarbonyl554 CH.sub.3 n-Butoxycarbonyl555 CH.sub.3 iso-Butoxycarbonyl556 CH.sub.3 sec.-Butoxycarbonyl557 CH.sub.3 tert.-Butoxycarbonyl558 CH.sub.3 n-Hexoxycarbonyl559 CH.sub.3 Phenoxycarbonyl560 CH.sub.3 4-Chlorophenoxy- carbonyl561 CH.sub.3 Benzyloxycarbonyl562 CH.sub.3 Aminocarbonyl563 CH.sub.3 Dimethylamino- carbonyl564 CH.sub.3 Diethylamino- carbonyl565 CH.sub.3 Di-iso-Propylamino- carbonyl566 CH.sub.3 Phenylaminocarbonyl567 CH.sub.3 N-Methyl-N-Phenyl- aminocarbonyl568 CH.sub.3 Phenyl569 CH.sub.3 2-Fluorophenyl m.p.: 89-91.degree. C.; IR (KBr): 1732, 1071, 1012, 998, 768570 CH.sub.3 3-Fluorophenyl m.p.: 83-85.degree. C.; IR (KBr): 1724, 1204, 1067, 1031, 1015, 955571 CH.sub.3 4-Fluorophenyl m.p.: 76-8.degree. C.; IR (KBr): 1737, 1510, 1302, 1224, 1072, 1031, 1015, 933572 CH.sub.3 Pentafluorophenyl573 CH.sub.3 2-Chlorophenyl574 CH.sub.3 3-Chlorophenyl m.p.: 61-63.degree. C.; IR (KBr): 1735, 1070, 1015, 1002, 785575 CH.sub.3 4-Chlorophenyl oil; IR (film): 1708, 1634, 1256, 1129576 CH.sub.3 Pentachlorophenyl577 CH.sub.3 2,3-Dichlorophenyl578 CH.sub.3 2,4-Dichlorophenyl579 CH.sub.3 2,5-Dichlorophenyl580 CH.sub.3 2,6-Dichlorophenyl581 CH.sub.3 3,4-Dichlorophenyl582 CH.sub.3 3,5-Dichlorophenyl m.p.: 95-7.degree. C.; IR (KBr): 1723, 1556, 1224, 1067, 1030, 1014, 957583 CH.sub.3 2,3,4-Trichlorophenyl m.p.: 118-20.degree. C.584 CH.sub.3 2,3,5-Trichlorophenyl585 CH.sub.3 2,3,6-Trichlorophenyl586 CH.sub.3 2,4,5-Trichlorophenyl587 CH.sub.3 2,4,6-Trichlorophenyl588 CH.sub.3 3,4,5-Trichlorophenyl589 CH.sub.3 2,3,4,6-Tetrachloro- phenyl590 CH.sub.3 2,3,5,6-Tetrachloro- phenyl591 CH.sub.3 2-Bromophenyl592 CH.sub.3 3-Bromophenyl m.p.: 80-4.degree. C.; IR (KBr): 1723, 1556, 1224, 1067, 1030, 1014, 957593 CH.sub.3 4-Bromophenyl m.p.: 73-75.degree. C.; IR (KBr): 1736, 1071, 1029, 1015, 932594 CH.sub.3 2,4-Dibromophenyl595 CH.sub.3 3-Bromo-4-fluorophenyl596 CH.sub.3 3-Bromo-4-methoxy- phenyl597 CH.sub.3 2-Iodophenyl598 CH.sub.3 3-Iodophenyl599 CH.sub.3 4-Iodophenyl600 CH.sub.3 2-Chloro-4-fluorophenyl601 CH.sub.3 2-Chloro-5-fluorophenyl602 CH.sub.3 2-Chloro-6-fluorophenyl603 CH.sub.3 2-Chloro-4-bromophenyl604 CH.sub.3 2-Bromo-4-chlorophenyl605 CH.sub.3 2-Bromo-4-fluorophenyl606 CH.sub.3 3-Bromo-4-chlorophenyl607 CH.sub.3 3-Chloro-4-fluorophenyl608 CH.sub.3 3-Fluoro-4-chlorophenyl609 CH.sub.3 2-Cyanophenyl610 CH.sub.3 3-Cyanophenyl611 CH.sub.3 4-Cyanophenyl612 CH.sub.3 2-Nitrophenyl613 CH.sub.3 3-Nitrophenyl614 CH.sub.3 4-Nitrophenyl m.p.: 88-90.degree. C.; IR (KBr): 1725, 1512, 1342, 1219, 1068, 1009, 854615 CH.sub.3 2-Methylphenyl616 CH.sub.3 3-Methylphenyl m.p.: 93-96.degree. C.617 CH.sub.3 4-Methylphenyl m.p.: 82-84.degree. C.; IR (KBr): 1722, 1068, 1038, 1015, 920618 CH.sub.3 2,4-Dimethylphenyl619 CH.sub.3 2,6-Dimethylphenyl620 CH.sub.3 3,4-Dimethylphenyl621 CH.sub.3 3,5-Dimethylphenyl622 CH.sub.3 2,3,4-Trimethylphenyl623 CH.sub.3 2,3,5-Trimethylphenyl624 CH.sub.3 2,3,6-Trimethylphenyl625 CH.sub.3 2,4,5-Trimethylphenyl626 CH.sub.3 2,4,6-Trimethylphenyl627 CH.sub.3 3,4,5-Trimethylphenyl628 CH.sub.3 Pentamethylphenyl629 CH.sub.3 2-Ethylphenyl630 CH.sub.3 3-Ethylphenyl631 CH.sub.3 4-Ethylphenyl632 CH.sub.3 3,5-Diethylphenyl633 CH.sub.3 2-n-Propylphenyl634 CH.sub.3 3-n-Propylphenyl635 CH.sub.3 4-n-Propylphenyl636 CH.sub.3 2-iso-Propylphenyl637 CH.sub.3 3-iso-Propylphenyl638 CH.sub.3 4-iso-Propylphenyl639 CH.sub.3 2,4-Di-iso-Propyl- phenyl640 CH.sub.3 3,5-Di-iso-Propyl- phenyl641 CH.sub.3 4-n-Butylphenyl642 CH.sub.3 4-sec.-Butylphenyl643 CH.sub.3 4-iso-Butylphenyl644 CH.sub.3 4-tert.-Butylphenyl m.p.: 45-50.degree. C.645 CH.sub.3 3-tert.-Butylphenyl646 CH.sub.3 2-tert.-Butylphenyl647 CH.sub.3 2,4-Di-tert.-Butyl- phenyl648 CH.sub.3 3,5-Di-tert.-Butyl- phenyl649 CH.sub.3 4-n-Hexylphenyl650 CH.sub.3 4-n-Dodecylphenyl651 CH.sub.3 2-Methyl-4-tert.-Butyl- phenyl652 CH.sub.3 2-Methyl-6-tert.-Butyl- phenyl653 CH.sub.3 2-Methyl-4-iso-Propyl- phenyl654 CH.sub.3 2-Methyl-4-Cyclohexyl- phenyl655 CH.sub.3 2-Methyl-4-Phenyl- phenyl656 CH.sub.3 2-Methyl-4-Benzyl- phenyl657 CH.sub.3 2-Methyl-4-Phenoxy- phenyl658 CH.sub.3 2-Methyl-4-Benzyloxy- phenyl659 CH.sub.3 2-Methyl-3-Chloro- phenyl660 CH.sub.3 2-Methyl-4-Chloro- phenyl661 CH.sub.3 2-Methyl-5-Chloro- phenyl662 CH.sub.3 2-Methyl-6-chloro- phenyl663 CH.sub.3 2-Methyl-4-fluoro- phenyl664 CH.sub.3 2-Methyl-3-bromo- phenyl665 CH.sub.3 2-Methyl-4-bromo- phenyl666 CH.sub.3 2-Methyl-3-methoxy- phenyl667 CH.sub.3 2-Methyl-4-methoxy- phenyl668 CH.sub.3 2-Methyl-5-methoxy- phenyl669 CH.sub.3 2-Methyl-6-methoxy- phenyl670 CH.sub.3 2-Methyl-4-iso- Propoxyphenyl671 CH.sub.3 2-Methyl-2,5- dimethoxyphenyl672 CH.sub.3 2-Methoxyphenyl m.p.: 74-6.degree. C.; IR (KBr): 1741, 1433, 1295, 1249, 1224, 1067, 1022, 878673 CH.sub.3 3-Methoxyphenyl674 CH.sub.3 4-Methoxyphenyl m.p.: 89-91.degree. C.675 CH.sub.3 2,3-Dimethoxyphenyl676 CH.sub.3 2,4-Dimethoxyphenyl677 CH.sub.3 2,5-Dimethoxyphenyl678 CH.sub.3 2,6-Dimethoxyphenyl679 CH.sub.3 3,4-Dimethoxyphenyl680 CH.sub.3 3,5-Dimethoxyphenyl681 CH.sub.3 3,6-Dimethoxyphenyl682 CH.sub.3 2,3,4-Trimethoxy- phenyl683 CH.sub.3 2,3,5-Trimethoxy- phenyl684 CH.sub.3 2,3,6-Trimethoxy- phenyl685 CH.sub.3 2,4,5-Trimethoxy- phenyl686 CH.sub.3 2,4,6-Trimethoxy- phenyl687 CH.sub.3 3,4,5-Trimethoxy- phenyl688 CH.sub.3 2-Ethoxyphenyl689 CH.sub.3 3-Ethoxyphenyl690 CH.sub.3 4-Ethoxyphenyl691 CH.sub.3 2-iso-Propoxyphenyl692 CH.sub.3 3-iso-Propoxyphenyl693 CH.sub.3 4-iso-Propoxyphenyl694 CH.sub.3 3-tert.-Butoxyphenyl695 CH.sub.3 4-tert.-Butoxyphenyl696 CH.sub.3 2-Trifluoromethoxy- phenyl697 CH.sub.3 3-Trifluoromethoxy- phenyl698 CH.sub.3 4-Trifluoromethoxy- phenyl699 CH.sub.3 3-(1',1',2',2'-Tetra- fluoro)ethoxyphenyl700 CH.sub.3 4-(1',1',2',2'-Tetra- fluoro)ethoxyphenyl701 CH.sub.3 2-Chloromethylphenyl702 CH.sub.3 3-Chloromethylphenyl703 CH.sub.3 4-Chloromethylphenyl704 CH.sub.3 2-Trifluoromethyl- m.p.: 78-80.degree. C.; phenyl IR (KBr): 1741, 1315, 1116, 1068, 1010705 CH.sub.3 3-Trifluoromethyl- m.p.: 70-72.degree. C.; phenyl IR (KBr): 1740, 1291, 1281, 1164, 1124, 1073, 1010706 CH.sub.3 4-Trifluoromethyl- m.p.: 57-58.degree. C.; phenyl (IR (KBr): 1728, 1333, 1318, 1106, 1069, 986707 CH.sub.3 2-(Methoxyimino- methyl)phenyl708 CH.sub.3 3-(Methoxyimino- methyl)phenyl709 CH.sub.3 4-(Methoxyimino- methyl)phenyl710 CH.sub.3 2-(Ethoxyimino- methyl)phenyl711 CH.sub.3 3-(Ethoxyimino- methyl)phenyl712 CH.sub.3 4-(Ethoxyimino- methyl)phenyl713 CH.sub.3 2-(n-Propoxyimino- methyl)phenyl714 CH.sub.3 3-(n-Propoxyimino- methyl)phenyl715 CH.sub.3 4-(n-Propoxyimino- methyl)phenyl716 CH.sub.3 2-(iso-Propoxyimino- methyl)phenyl717 CH.sub.3 3-(iso-Propoxyimino- methyl)phenyl718 CH.sub.3 4-(iso-Propoxyimino- methyl)phenyl719 CH.sub.3 2-(n-Butoxyimino- methyl)phenyl720 CH.sub.3 3-(n-Butoxyimino- methyl)phenyl721 CH.sub.3 4-(n-Butoxyimino- methyl)phenyl722 CH.sub.3 2-(iso-Butoxyimino- methyl)phenyl723 CH.sub.3 3-(iso-Butoxyimino- methyl)phenyl724 CH.sub.3 4-(iso-Butoxyimino- methyl)phenyl725 CH.sub.3 2-(tert.-Butoxyimino- methyl)phenyl726 CH.sub.3 3-(tert.-Butoxyimino- methyl)phenyl727 CH.sub.3 4-(tert.-Butoxyimino- methyl)phenyl728 CH.sub.3 2-(n-Pentoxyimino- methyl)phenyl729 CH.sub.3 3-(n-Pentoxyimino- methyl)phenyl730 CH.sub.3 4-(n-Pentoxyimino- methyl)phenyl731 CH.sub.3 2-(n-Hexoxyimino- methyl)phenyl732 CH.sub.3 3-(n-Hexoxyimino- methyl)phenyl733 CH.sub.3 4-(n-Hexoxyimino- methyl)phenyl734 CH.sub.3 2-(Allyloxyimino- methyl)phenyl735 CH.sub.3 3-(Allyloxyimino- methyl)phenyl736 CH.sub.3 4-(Allyloxyimino- methyl)phenyl737 CH.sub.3 2-(Benzyloxyimino- methyl)phenyl738 CH.sub.3 3-(Benzyloxyimino- methyl)phenyl739 CH.sub.3 4-(Benzyloxyimino- methyl)phenyl740 CH.sub.3 2-(Methoxyimino-1'- ethyl)phenyl741 CH.sub.3 3-(Methoxyimino-1'- ethyl)phenyl742 CH.sub.3 4-(Methoxyimino-1'- ethyl)phenyl743 CH.sub.3 2-(Ethoxyimino-1'- ethyl)phenyl744 CH.sub.3 3-(Ethoxyimino-1'- ethyl)phenyl745 CH.sub.3 4-(Ethoxyimino-1'- ethyl)phenyl746 CH.sub.3 2-(n-Propoxyimino-1'- ethyl)phenyl747 CH.sub.3 3-(n-Propoxyimino-1'- ethyl)phenyl748 CH.sub.3 4-(n-Propoxyimino-1'- ethyl)phenyl749 CH.sub.3 2-(n-Butoxyamino-1'- ethyl)phenyl750 CH.sub.3 3-(n-Butoxyamino-1'- ethyl)phenyl751 CH.sub.3 4-(n-Butoxyamino-1'- ethyl)phenyl752 CH.sub.3 2-(n-Pentoxyimino-1'- ethyl)phenyl753 CH.sub.3 3-(n-Pentoxyimino-1'- ethyl)phenyl754 CH.sub.3 4-(n-Pentoxyimino-1'- ethyl)phenyl755 CH.sub.3 2-(n-Hexoxyimino-1'- ethyl)phenyl756 CH.sub.3 3-(n-Hexoxyimino-1'- ethyl)phenyl757 CH.sub.3 4-(n-Hexoxyimino-1'- ethyl)phenyl758 CH.sub.3 2-(Allyloxyimino-1'- ethyl)phenyl759 CH.sub.3 3-(Allyloxyimino-1'- ethyl)phenyl760 CH.sub.3 4-(Allyloxyimino-1'- ethyl)phenyl761 CH.sub.3 2-(Benzyloxyimino-1'- ethyl)phenyl762 CH.sub.3 3-(Benzyloxyimino-1'- ethyl)phenyl763 CH.sub.3 4-(Benzyloxyimino-1'- ethyl)phenyl764 CH.sub.3 2-Phenylphenyl765 CH.sub.3 3-Phenylphenyl766 CH.sub.3 4-Phenylphenyl767 CH.sub.3 2-Phenoxyphenyl768 CH.sub.3 3-Phenoxyphenyl769 CH.sub.3 4-Phenoxyphenyl m.p.: 91-3.degree. C.; IR (KBr): 1732, 1587, 1491, 1241, 1071, 1014, 995, 769770 CH.sub.3 2-Benzyloxyphenyl771 CH.sub.3 3-Benzyloxyphenyl772 CH.sub.3 4-Benzyloxyphenyl773 CH.sub.3 4-(Imidazol-1'- yl)phenyl774 CH.sub.3 4-(Piperazin-1'- yl)phenyl775 CH.sub.3 4-(Morpholin-1'- yl)phenyl776 CH.sub.3 4-(Piperidin-1'- yl)phenyl777 CH.sub.3 4-(Pyridyl-2'- oxy)phenyl778 CH.sub.3 2-Cyclopropylphenyl779 CH.sub.3 3-Cyclopropylphenyl780 CH.sub.3 4-Cyclopropylphenyl781 CH.sub.3 3-Cyclohexylphenyl782 CH.sub.3 4-Cyclohexylphenyl m.p.: 53-5.degree. C.783 CH.sub.3 4-Oxiranylphenyl784 CH.sub.3 4-(1',3'-Dioxan-2'- phenyl785 CH.sub.3 4-(Tetrahydropyran-2- yloxy)phenyl786 CH.sub.3 1-Naphthyl787 CH.sub.3 2-Naphthyl788 CH.sub.3 9-Anthryl789 CH.sub.3 1-Naphthoxy790 CH.sub.3 2-Naphthoxy791 CH.sub.3 9-Anthroxy792 CH.sub.3 Phenoxy793 CH.sub.3 2-Chlorophenoxy794 CH.sub.3 3-Chlorophenoxy795 CH.sub.3 4-Chlorophenoxy796 CH.sub.3 4-Methylphenoxy797 CH.sub.3 4-tert.-Butylphenoxy798 CH.sub.3 4-Methoxyphenoxy799 CH.sub.3 4-Ethoxyphenoxy800 CH.sub.3 4-tert.-Butoxyphenoxy801 CH.sub.3 Phenylthio802 CH.sub.3 2-Chlorophenylthio803 CH.sub.3 4-Chlorophenylthio804 CH.sub.3 Benzyl805 CH.sub.3 2-Methylbenzyl806 CH.sub.3 3-Methylbenzyl807 CH.sub.3 4-Methylbenzyl808 CH.sub.3 4-tert.-Butylbenzyl809 CH.sub.3 2-Chlorobenzyl810 CH.sub.3 3-Chlorobenzyl811 CH.sub.3 4-Chlorobenzyl812 CH.sub.3 2,4-Dichlorobenzyl813 CH.sub.3 2,6-Dichlorobenzyl814 CH.sub.3 2,4,6-Trichlorobenzyl815 CH.sub.3 2-Trifluoromethyl- benzyl816 CH.sub.3 3-Trifluoromethyl- benzyl817 CH.sub.3 4-Trifluoromethyl- benzyl818 CH.sub.3 2-Methoxybenzyl819 CH.sub.3 4-Methoxybenzyl820 CH.sub.3 4-tert.-Butoxybenzyl821 CH.sub.3 4-Phenoxybenzyl822 CH.sub.3 1-Phenethyl823 CH.sub.3 2-Phenethyl824 CH.sub.3 1-Phenylpropyl825 CH.sub.3 2-Phenylpropyl826 CH.sub.3 3-Phenylpropyl827 CH.sub.3 2-Methyl-2-phenyl- propyl828 CH.sub.3 2-Methyl-3-phenyl- propyl829 CH.sub.3 4-Phenylbutyl830 CH.sub.3 2-Phenyl-1-ethenyl831 CH.sub.3 1-Phenyl-1-ethenyl832 CH.sub.3 1-Phenyl-1-propenyl833 CH.sub.3 1-Phenyl-1-propen-2-yl834 CH.sub.3 2,2-Diphenylethenyl835 CH.sub.3 Phenoxymethyl836 CH.sub.3 2-Pyridyl837 CH.sub.3 3-Pyridyl838 CH.sub.3 4-Pyridyl839 CH.sub.3 2,6-Pyrimidinyl840 CH.sub.3 1,5-Pyrimidinyl841 CH.sub.3 2-Thienyl842 CH.sub.3 3-Thienyl843 CH.sub.3 2-Furyl844 CH.sub.3 3-Furyl845 CH.sub.3 1-Pyrrolyl846 CH.sub.3 1-Imidazolyl847 CH.sub.3 1,2,4-Triazolyl848 CH.sub.3 1,3,4-Triazolyl849 CH.sub.3 4-Thiazolyl850 CH.sub.3 2-Benzothiazolyl851 CH.sub.3 2-Pyridyloxy852 CH.sub.3 2-Pyrimidinyloxy853 CH.sub.3 2-Pyridylthio854 CH.sub.3 2-Pyrimidinylthio855 CH.sub.3 2-Benzothiazolylthio856 CH.sub.3 Phenylthiomethyl857 CH.sub.3 2-Pyridylmethyl858 CH.sub.3 3-Pyridylmethyl859 CH.sub.3 Furfuryloxy860 CH.sub.3 Thienylmethoxy861 CH.sub.3 3-Isoxazolylmethoxy862 CH.sub.3 2-Oxazolylmethoxy863 CH.sub.3 2-Pyridylmethoxy864 CH.sub.3 2'-Furyl-2-ethenyl865 CH.sub.3 2'-Thienyl-2-ethenyl866 CH.sub.3 3'-Pyridyl-2-ethenyl867 CH.sub.3 Oxiranyl868 CH.sub.3 1-Aziridinyl869 CH.sub.3 1-Azetidinyl870 CH.sub.3 1-Pyrrolidinyl871 CH.sub.3 2-Tetrahydrofuryl872 CH.sub.3 2-Tetrahydropyranyl873 CH.sub.3 3-Tetrahydropyranyl874 CH.sub.3 1-Piperidinyl875 CH.sub.3 1-Morpholinyl876 CH.sub.3 1-Piperazinyl877 CH.sub.3 1,3-Dioxan-2-yl878 CH.sub.3 3-Tetrahydrothio- pyranyl879 CH.sub.3 2-Dihydropyranyloxy880 CH.sub.3 2-Tetrahydro- pyranyloxy881 CH.sub.3 CF.sub.3882 CH.sub.3 2-Fluoroethyl883 CH.sub.3 2,2,2-Trifluoroethyl884 CH.sub.3 Pentafluoroethyl885 CH.sub.3 Chloromethyl886 CH.sub.3 Dichloromethyl887 CH.sub.3 Trichloromethyl888 CH.sub.3 2-Chloroethyl889 CH.sub.3 2,2,2-Trichloroethyl890 CH.sub.3 Pentachloroethyl891 CH.sub.3 Cyclopropyl892 CH.sub.3 Cyclobutyl893 CH.sub.3 Cyclopentyl894 CH.sub.3 Cyclohexyl895 CH.sub.3 1-Methylcyclopropyl896 CH.sub.3 2,2-Dimethylcyclopropyl897 CH.sub.3 1-Methylcyclohexyl898 CH.sub.3 2,2-Difluorocyclopropyl-899 CH.sub.3 2,2-Dichlorocyclopropyl900 CH.sub.3 2,2-Dibromocyclopropyl901 CH.sub.3 2,2-Dichloro-3- Methylcyclopropyl902 CH.sub.3 2,2,3,3-Tetrafluoro- cyclobutyl903 CH.sub.3 Ethenyl904 CH.sub.3 1-Propenyl905 CH.sub.3 2-Methyl-1-propenyl906 CH.sub.3 4-Methylpent-3-en-1-yl907 CH.sub.3 2-Propenyl908 CH.sub.3 2-Butenyl909 CH.sub.3 1-Methyl-2-propenyl910 CH.sub.3 3-Methyl-2-butenyl911 CH.sub.3 2,2-Difluoroethenyl912 CH.sub.3 2,2-Dichloroethenyl913 CH.sub.3 3,3,3-Trifluoropropenyl914 CH.sub.3 3,3,3-Trichloropropenyl915 CH.sub.3 3-Chloro-2-propenyl916 CH.sub.3 Cyclopent-1-enyl917 CH.sub.3 Cyclopentadienyl918 CH.sub.3 Cyclohex-1-enyl919 CH.sub.3 Pentafluorocyclo- pentadienyl920 CH.sub.3 Pentachlorocyclo- pentadienyl921 Phenyl Phenyl922 Phenyl 2-Fluorophenyl923 Phenyl 4-Fluorophenyl924 Phenyl 2-Chlorophenyl925 Phenyl 3-Chlorophenyl926 Phenyl 4-Chlorophenyl927 Phenyl 3,4-Dichlorophenyl928 Phenyl 4-Nitrophenyl929 Phenyl 2-CF.sub.3 -Phenyl930 Phenyl 3-CF.sub.3 -Phenyl931 Phenyl 4-CF.sub.3 -Phenyl932 Phenyl 2-Methylphenyl933 Phenyl 3-Methylphenyl934 Phenyl 4-Methylphenyl935 Phenyl 2,4-Dimethylphenyl936 Phenyl 4-tert.-Butylphenyl937 Phenyl 4-Methoxyphenyl938 4-Fluoro- 4-Fluorophenyl phenyl939 2-Fluoro- 4-Fluorophenyl phenyl940 2-Chloro- 4-Fluorophenyl phenyl941 2-Chloro- 2-Chlorophenyl phenyl942 3-Chloro- 3-Chlorophenyl phenyl943 4-Chloro- 4-Chlorophenyl phenyl944 2-Chloro- 4-Chlorophenyl phenyl945 4-Methoxy- 4-Methoxyphenyl phenyl946 4-Dimethyl- 4-Dimethylamino- aminophenyl phenyl947 Phenyl Naphthyl948 Ethyl Ethyl949 Ethyl n-Propyl950 Ethyl iso-Propyl951 Ethyl n-Butyl952 Ethyl iso-Butyl953 Ethyl 2-Methyl-butyl954 Ethyl Benzyl955 n-Propyl n-Propyl956 iso-Propyl iso-Propyl957 n-Butyl n-Butyl958 iso-Butyl iso-Butyl959 tert.-Butyl tert.-Butyl960 Benzyl Benzyl961 Penta- Pentachloroethyl chloroethyl962 n-Hexyl n-Hexyl963 Ethoxy- Ethoxycarbonyl carbonyl964 Phenyl Benzoyl965 Ethyl Phenyl966 n-Butyl Phenyl967 Styryl Styryl968 2-Pyridyl 2-Pyridyl969 3-Pyridyl 3-Pyridyl970 Ethyl 2-Pyridyl m.p.: 84-86.degree. C.971 ##STR27## m.p.: 103-105.degree. C.______________________________________
TABLE III - ##STR28## N o. X Y R.sup.1 R.sup.2 = H R.sup.3 R.sup.4 Data 1 CHSCH.sub.3 O CH.sub.3 CF.sub.3 Phenyl 2 CHSCH.sub.3 O CH.sub.3 Cyclopropyl Phenyl 3 CHSCH.sub.3 O CH.sub.3 Cyclopropyl 4-Chlorophenyl 4 CHSCH.sub.3 O CH.sub.3 Cyclopropyl 4-Methoxyphenyl 5 CHSCH.sub.3 O CH.sub.3 Cyclopropyl 4-tert.-Butylphenyl 6 CHSCH.sub.3 O CH.sub.3 CN Methylthio 7 CHSCH.sub.3 O CH.sub.3 CN 2-Methoxyprop-2-yl 8 CHSCH.sub.3 O CH.sub.3 CN 2-Methylthloprop-2-yl 9 CHSCH.sub.3 O CH.sub.3 CN Phenylthio 10 CHSCH.sub.3 O CH.sub.3 CN iso-Propyl 11 CHSCH.sub.3 O CH.sub.3 CN CN 12 CHSCH.sub.3 O CH.sub.3 CN Acetyl 13 CHSCH.sub.3 O CH.sub.3 CN Benzoyl 14 CHSCH.sub.3 O CH.sub.3 CN Methoxycarbonyl 15 CHSCH.sub.3 O CH.sub.3 CN Phenyl 16 CHSCH.sub.3 O CH.sub.3 CN 2-Chlorophenyl 17 CNSCH.sub.3 O CH.sub.3 CN 4-Chlorophenyl 18 CHSCH.sub.3 O CH.sub.3 CN 2-Methylphenyl 19 CHSCH.sub.3 O CH.sub.3 CN 4-tert.-Butylphenyl 20 CHSCH.sub.3 O CH.sub.3 CN 4-(n-Butoxylminomethyl)phenyl 21 CHSCH.sub.3 O CH.sub.3 CN 2-Pyridyl 22 CNSCH.sub.3 O CH.sub.3 CN Styryl 23 CHSCH.sub.3 O CH.sub.3 CN 1-Propenyl 24 CHSCH.sub.3 O CH.sub.3 CH.sub.3 Phenylthio 25 CHSCH.sub.3 O CH.sub.3 CH.sub.3 Benzyl 26 CHSCH.sub.3 O CH.sub.3 CH.sub.3 tert.-Butyl 27 CHSCH.sub.3 O CH.sub.3 CH.sub.3 iso-Propyl 28 CHSCH.sub.3 O CH.sub.3 CH.sub.3 2-Methylbutyl 29 CHSCH.sub.3 O CH.sub.3 CH.sub.3 iso-Butyl 30 CHSCH.sub.3 O CH.sub.3 CH.sub.3 Phenyl 31 CHSCH.sub.3 O CH.sub.3 CH.sub.3 2-Chlorophenyl 32 CHSCH.sub.3 O CH.sub.3 CH.sub.3 4-Chlorophenyl 33 CHSCH.sub.3 O CH.sub.3 CH.sub.3 2-Methylphenyl 34 CHSCH.sub.3 O CH.sub.3 CH.sub.3 Naphthyl 35 CHSCH.sub.3 O CH.sub.3 CH.sub.3 1-Pyridyl 36 CHSCH.sub.3 O CH.sub.3 iso-Butyl iso-Butyl 37 CHSCH.sub.3 O CH.sub.3 Phenyl Phenyl 38 CHSCH.sub.3 O CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 39 CHSCH.sub.3 O CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 40 CHCH.sub.3 O C H.sub.3 CF.sub.3 Phenyl 41 CHCH.sub.3 O CH.sub.3 Cyclopropyl Phenyl 42 CHCH.sub.3 O CH.sub.3 Cyclopropyl 4-Chlorophenyl 43 CHCH.sub.3 O CH.sub.3 Cyclopropyl 4-Methoxyphenyl 44 CHCH.sub.3 O CH.sub.3 Cyclopropyl 4-tert.-Butylphenyl 45 CHCH.sub.3 O CH.sub.3 CN Methylthio 46 CHCH.sub.3 O CH.sub.3 CN 2-Methoxyprop-2-yl IR (film): 1717,13 36,1367,1256,1210,1179, 1070,1037,1009,759 47 CHCH.sub.3 O CH.sub.3 CN 2-Methylthloprop-2-yl .sup.1 H-NMR (CDCl.sub.3): .delta. = 1.45s, 1.6d, 1.8s, 3.7s, 5.1s, 7.1-7.5m 48 CHCH.sub.3 O CH.sub.3 CN Phenylthio 49 CHCH.sub.3 O CH.sub.3 CN iso-Propyl .sup.1 H-NMR (CDCl.sub.3): .delta. = 1.2d, 1.6d, 2.7m, 3.67s, 5.1s, 7.0-7.5m 50 CHCH.sub.3 O CH.sub.3 CN CN 51 CHCH.sub.3 O CH.sub.3 CN Acetyl 52 CHCH.sub.3 O CH.sub.3 CN Benzoyl 53 CHCH.sub.3 O CH.sub.3 CN Methoxycarbonyl 54 CHCH.sub.3 O CH.sub.3 CN Phenyl .sup.1 H-NMR (CDCl.sub.3): .delta. = 1.6d, 3.7s, 5.2s, 7.0-1.8m 55 CHCH.sub.3 O CH.sub.3 CN 2-Chlorophenyl 56 CHCH.sub.3 O CH.sub.3 CN 4-Chlorophenyl 57 CHCH.sub.3 O CH.sub.3 CN 2-Methylphenyl 58 CHCH.sub.3 O CH.sub.3 CN 4-tert.-Butylphenyl 59 CHCH.sub.3 O CH.sub.3 CN 4-(n-Butoxylmlnomethyl)phenyl 60 CHCH.sub.3 O CH.sub.3 CN 2-Pyridyl 61 CHCH.sub.3 O CH.sub.3 CN Styryl 62 CHCH.sub.3 O CH.sub.3 CN 1-Propenyl 63 CHCH.sub.3 O CH.sub.3 CH.sub.3 Phenylthio 64 CHCH.sub.3 O CH.sub.3 CH.sub.3 Benzyl 65 CHCH.sub.3 O CH.sub.3 CH.sub.3 tert.-Butyl 66 CHCH.sub.3 O CH.sub.3 CH.sub.3 iso-Propyl 67 CHCH.sub.3 O CH.sub.3 CH.sub.3 2-Methylbutyl 68 CHCH.sub.3 O CH.sub.3 CH.sub.3 iso-Butyl 69 CHCH.sub.3 O CH.sub.3 CH.sub.3 Phenyl 70 CHCH.sub.3 O CH.sub.3 CH.sub.3 2-Chlorophenyl 71 CHCH.sub.3 O CH.sub.3 CH.sub.3 4-Chlorophenyl IR (film): 1716,13 90,13 34,1253,1206,1096, 1036,1012,820,760 72 CHCH.sub.3 O CH.sub.3 CH.sub.3 2-Methylphenyl 73 CHCH.sub.3 O CH.sub.3 CH.sub.3 Naphthyl 74 CHCH.sub.3 O CH.sub.3 CH.sub.3 1-Pyridyl 75 CHCH.sub.3 O CH.sub.3 iso-Butyl iso-Butyl 76 CHCH.sub.3 O CH.sub.3 Phenyl Phenyl 77 CHCH.sub.3 O CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 78 CHCH.sub.3 O CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 79 CH.sub.2 O CH.sub.3 CF.sub.3 Phenyl 80 CH.sub.2 O CH.sub.3 Cyclopropyl Phenyl 81 CH.sub.2 O CH.sub.3 Cyclopropyl 4-Chlorophenyl 82 CH.sub.2 O CH.sub.3 Cyclopropyl 4-Methoxyphenyl 83 CH.sub.2 O CH.sub.3 Cyclopropyl 4-tert.-Butylphenyl 84 CH.sub.2 O CH.sub.3 CN Methylthio 85 CH.sub.2 O CH.sub.3 CN 2-Methoxyprop-2-yl 86 CH.sub.2 O CH.sub.3 CN 2-Methylthloprop-2-yl 87 CH.sub.2 O CH.sub.3 CN Phenylthio 88 CH.sub.2 O CH.sub.3 CN iso-Propyl 89 CH.sub.2 O CH.sub.3 CN CN 90 CH.sub.2 O CH.sub.3 CN Acetyl 91 CH.sub.2 O CH.sub.3 CN Benzoyl 92 CH.sub.2 O CH.sub.3 CN Methoxycarbonyl 93 CH.sub.2 O CH.sub.3 CN Phenyl 94 CH.sub.2 O CH.sub.3 CN 2-Chlorophenyl 95 CH.sub.2 O CH.sub.3 CN 4-Chlorophenyl 96 CH.sub.2 O CH.sub.3 CN 2-Methylphenyl 97 CH.sub.2 O CH.sub.3 CN 4-tert.-Butylphenyl 98 CH.sub.2 O CH.sub.3 CN 4-(n-Butoxylminomethyl)phenyl 99 CH.sub.2 O CH.sub.3 CN 2-Pyridyl 100 CH.sub.2 O CH.sub.3 CN Styryl 101 CH.sub.2 O CH.sub.3 CN 1-Propenyl 102 CH.sub.2 O CH.sub.3 CH.sub.3 Phenylthio 103 CH.sub.2 O CH.sub.3 CH.sub.3 Benzyl 104 CH.sub.2 O CH.sub.3 CH.sub.3 tert.-Butyl 105 CH.sub.2 O CH.sub.3 CH.sub.3 iso-Propyl 106 CH.sub.2 O CH.sub.3 CH.sub.3 2-Methylbutyl 107 CH.sub.2 O CH.sub.3 CH.sub.3 iso-Butyl 108 CH.sub.2 O CH.sub.3 CH.sub.3 Phenyl 109 CH.sub.2 O CH.sub.3 CH.sub.3 2-Chlorophenyl 110 CH.sub.2 O CH.sub.3 CH.sub.3 4-Chlorophenyl 111 CH.sub.2 O CH.sub.3 CH.sub.3 2-methylphenyl 112 CH.sub.2 O CH.sub.3 CH.sub.3 Naphthyl 113 CH.sub.2 O CH.sub.3 CH.sub.3 1-Pyridyl 114 CH.sub.2 O CH.sub.3 iso-Butyl iso-Butyl 115 CH.sub.2 O CH.sub.3 Phenyl Phenyl 116 CH.sub.2 O CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 117 CH.sub.2 O CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 118 NOCH.sub.3 S CH.sub.3 CF.sub.3 Phenyl 119 NOCH.sub.3 S CH.sub.3 Cyclopropyl Phenyl 120 NOCH.sub.3 S CH.sub.3 Cyclopropyl 4-Chlorophenyl 121 NOCH.sub.3 S CH.sub.3 Cyclopropyl 4-Methoxyphenyl 122 NOCH.sub.3 S CH.sub.3 Cyclopropyl 4-tert.-Butylphenyl 123 NOCH.sub.3 S CH.sub.3 CN Methylthio 124 NOCH.sub.3 S CH.sub.3 CN 2-Methoxyprop-2-yl 125 NOCH.sub.3 S CH.sub.3 CN 2-Methylthioprop-2-yl 126 NOCH.sub.3 S CH.sub.3 CN Phenylthio 127 NOCH.sub.3 S CH.sub.3 CN iso-Propyl 128 NOCH.sub.3 S CH.sub.3 CN CN 129 NOCH.sub.3 S CH.sub.3 CN Acetyl 130 NOCH.sub.3 S CH.sub.3 CN Benzoyl 131 NOCH.sub.3 S CH.sub.3 CN Methoxycarbonyl 132 NOCH.sub.3 S CH.sub.3 CN Phenyl 133 NOCH.sub.3 S CH.sub.3 CN 2-Chlorophenyl 134 NOCH.sub.3 S CH.sub.3 CN 4-Chlorophenyl 135 NOCH.sub.3 S CH.sub.3 CN 2-Methylphenyl 136 NOCH.sub.3 S CH.sub.3 CN 4-tert.-Butylphenyl 137 NOCH.sub.3 S CH.sub.3 CN 4-(n-Butoxylminomethyl)phenyl 138 NOCH.sub.3 S CH.sub.3 CN 2-Pyridyl 139 NOCH.sub.3 S CH.sub.3 CN Styryl 140 NOCH.sub.3 S CH.sub.3 CN 1-Propenyl 141 NOCH.sub.3 S CH.sub.3 CH.sub.3 Phenylthio 142 NOCH.sub.3 S CH.sub.3 CH.sub.3 Benzyl 143 NOCH.sub.3 S CH.sub.3 CH.sub.3 tert.-Butyl 144 NOCH.sub.3 S CH.sub.3 CH.sub.3 iso-Propyl 145 NOCH.sub.3 S CH.sub.3 CH.sub.3 2-Methylbutyl 146 NOCH.sub.3 S CH.sub.3 CH.sub.3 iso-Butyl 147 NOCH.sub.3 S CH.sub.3 CH.sub.3 Phenyl 148 NOCH.sub.3 S CH.sub.3 CH.sub.3 2-Chlorophenyl 149 NOCH.sub.3 S CH.sub.3 CH.sub.3 4-Chlorophenyl 150 NOCH.sub.3 S CH.sub.3 CH.sub.3 2-Methylphenyl 151 NOCH.sub.3 S CH.sub.3 CH.sub.3 Naphthyl 152 NOCH.sub.3 S CH.sub.3 CH.sub.3 1-Pyridyl 153 NOCH.sub.3 S CH.sub.3 iso-Butyl iso-Butyl 154 NOCH.sub.3 S CH.sub.3 Phenyl Phenyl 155 NOCH.sub.3 S CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 156 NOCH.sub.3 S CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 157 NOCH.sub.3 NH CH.sub.3 CF.sub.3 Phenyl 158 NOCH.sub.3 NH CH.sub.3 Cyclopropyl Phenyl 159 NOCH.sub.3 NH CH.sub.3 Cyclopropyl 4-Chlorophenyl m.p.: 71-74.degree . C. IR (KBr): 3348,1663,1529,1042,1030,982 160 NOCH.sub.3 NH CH.sub.3 Cyclopropyl 4-Methoxyphenyl 161 NOCH.sub.3 NH CH.sub.3 Cyclopropyl 4-tert.-Butylphenyl 162 NOCH.sub.3 NH CH.sub.3 CN Methylthio 163 NOCH.sub.3 NH CH.sub.3 CN 2-Methoxyprop-2-yl 164 NOCH.sub.3 NH CH.sub.3 CN 2-Methylthioprop-2-yl 165 NOCH.sub.3 NH CH.sub.3 CN Phenylthio 166 NOCH.sub.3 NH CH.sub.3 CN iso-Propyl 167 NOCH.sub.3 NH CH.sub.3 CN CN 168 NOCH.sub.3 NH CH.sub.3 CN Acetyl 169 NOCH.sub.3 NH CH.sub.3 CN Benzoyl 170 NOCH.sub.3 NH CH.sub.3 CN Methoxycarbonyl 171 NOCH.sub.3 NH CH.sub.3 CN Phenyl 172 NOCH.sub.3 NH CH.sub.3 CN 2-Chlorophenyl 173 NOCH.sub.3 NH CH.sub.3 CN 4-Chlorophenyl 174 NOCH.sub.3 NH CH.sub.3 CN 2-Methylphenyl 175 NOCH.sub.3 NH CH.sub.3 CN 4-tert.-Butylphenyl 176 NOCH.sub.3 NH CH.sub.3 CN 4-(n-Butoxyiminomethyl)phenyl 177 NOCH.sub.3 NH CH.sub.3 CN 2-Pyridyl 178 NOCH.sub.3 NH CH.sub.3 CN Styryl 179 NOCH.sub.3 NH CH.sub.3 CN 1-Propenyl 180 NOCH.sub.3 NH CH.sub.3 CH.sub.3 Phenylthio 181 NOCH.sub.3 NH CH.sub.3 CH.sub.3 Benzyl 182 NOCH.sub.3 NH CH.sub.3 CH.sub.3 tert.-Butyl 183 NOCH.sub.3 NH CH.sub.3 CH.sub.3 iso-Propyl 184 NOCH.sub.3 NH CH.sub.3 CH.sub.3 2-Methylbutyl 185 NOCH.sub.3 NH CH.sub.3 CH.sub.3 iso-Butyl 186 NOCH.sub.3 NH CH.sub.3 CH.sub.3 Phenyl 187 NOCH.sub.3 NH CH.sub.3 CH.sub.3 2-Chlorophenyl 188 NOCH.sub.3 NH CH.sub.3 CH.sub.3 4-Chlorophenyl m.p.: 119-121.degree. C. IR (KOr): 3421,1676,1037,985,933,752 189 NOCH.sub.3 NH CH.sub.3 CH.sub.3 2-Methylphenyl No. X Y R.sup.1 R.sup.2 R.sup.3 R.sup.4 Data 190 NOCH.sub.3 NH CH.sub.3 H CH.sub.3 Naphthyl 191 NOCH.sub.3 NH CH.sub.3 H CH.sub.3 1-Pyridyl 192 NOCH.sub.3 NH CH.sub.3 H iso-Butyl iso-Butyl 193 NOCH.sub.3 NH CH.sub.3 H Phenyl Phenyl 194 NOCH.sub.3 NH CH.sub.3 H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 195 NOCH.sub.3 NH CH.sub.3 H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 196 NOCH.sub.3 O C.sub.2 H.sub.5 H CH.sub.3 Phenyl 197 CHOCH.sub.3 O C.sub.2 H.sub.5 H CH.sub.3 Phenyl 198 NOCH.sub.3 O n-C.sub.3 H.sub.5 H CH.sub.3 Phenyl 199 CHOCH.sub.3 O n-C.sub.3 H.sub.5 H CH.sub.3 Phenyl 200 CHC.sub.2 H.sub.5 O CH.sub.3 H CH.sub.3 Phenyl 201 NOCH.sub.3 O CH.sub.3 CH.sub.3 CH.sub.3 Phenyl 202 CHOCH.sub.3 O CH.sub.3 CH.sub.3 CH.sub.3 Phenyl 203 NOCH.sub.3 O CH.sub.3 CH.sub.3 CN Phenyl 204 CHOCH.sub.3 O CH.sub.3 CH.sub.3 CN Phenyl 205 CHSCH.sub.3 O CH.sub.3 H H Phenyl 206 CHCH.sub.3 O CH.sub.3 H H Phenyl 207 CH.sub.2 O CH.sub.3 H H Phenyl 208 NOCH.sub.3 S CH.sub.3 H H Phenyl 209 CHOCH.sub.3 S CH.sub.3 H H Phenyl 210 CHOCH.sub.3 NH CH.sub.3 H H Phenyl 211 NOCH.sub.3 NH CH.sub.3 H H Phenyl 212 CHOCH.sub.3 S CH.sub.3 H CN Methylthio No. X Y R.sup.1 R.sup.2 = H R.sup.3 R.sup.4 Data 213 CHOCH.sub.3 S CH.sub.3 CN 2-Methoxyprop-2-yl 214 CHOCH.sub.3 S CH.sub.3 CN 2-Methylthloprop-2-yl 215 CHOCH.sub.3 S CH.sub.3 CN Phenylthio 216 CHOCH.sub.3 S CH.sub.3 CN iso-Propyl 217 CHOCH.sub.3 S CH.sub.3 CN CN 218 CHOCH.sub.3 S CH.sub.3 CN Acthyl 219 CHOCH.sub.3 S CH.sub.3 CN Benzoyl 220 CHOCH.sub.3 S CH.sub.3 CN Methoxycarbonyl 221 CHOCH.sub.3 S CH.sub.3 CN Phenyl 222 CHOCH.sub.3 S CH.sub.3 CN 2-Chlorophenyl 223 CHOCH.sub.3 S CH.sub.3 CN 4-Chlorophenyl 224 CHOCH.sub.3 S CH.sub.3 CN 2-methylphenyl 225 CHOCH.sub.3 S CH.sub.3 CN 4-tert.-Butylphenyl 226 CHOCH.sub.3 S CH.sub.3 CN 4-(n-Butoxyiminomethyl)phenyl 227 CHOCH.sub.3 S CH.sub.3 CN 2-Pyridyl 228 CHOCH.sub.3 S CH.sub.3 CN Styryl 229 CHOCH.sub.3 S CH.sub.3 CN 1-Propenyl 230 CHOCH.sub.3 NH CH.sub.3 CN Methylthio 231 CHOCH.sub.3 NH CH.sub.3 CN 2-Methoxyprop-2-yl 232 CHOCH.sub.3 NH CH.sub.3 CN 2-Methylthioprop-2-yl 233 CHOCH.sub.3 NH CH.sub.3 CN Phenylthio 234 CHOCH.sub.3 NH CH.sub.3 CN iso-Propyl 235 CHOCH.sub.3 NH CH.sub.3 CN CN 236 CHOCH.sub.3 NH CH.sub.3 CN Acthyl 237 CHOCH.sub.3 NH CH.sub.3 CN Benzoyl 238 CHOCH.sub.3 NH CH.sub.3 CN Methoxycarbonyl 239 CHOCH.sub.3 NH CH.sub.3 CN Phenyl 240 CHOCH.sub.3 NH CH.sub.3 CN 2-Chlorophenyl 241 CHOCH.sub.3 NH CH.sub.3 CN 4-Chlorophenyl 242 CHOCH.sub.3 NH CH.sub.3 CN 2-Methylphenyl 243 CHOCH.sub.3 NH CH.sub.3 CN 4-tert.-Butylphenyl 244 CHOCH.sub.3 NH CH.sub.3 CN 4-(n-Butoxylminomethyl)phenyl 245 CHOCH.sub.3 NH CH.sub.3 CN 2-Pyridyl 246 CHOCH.sub.3 NH CH.sub.3 CN Styryl 247 CHOCH.sub.3 NH CH.sub.3 CN 1-Propenyl 248 NOCH.sub.3 NH CH.sub.3 CH.sub.3 3-Chlorphenyl m.p.: 71-74.degree. C.; 249 NOCH.sub.3 NH CH.sub.3 CH.sub.3 3,5-Dichlorphenyl m.p.: 94-97.degre e. C.; 250 NOCH.sub.3 NH CH.sub.3 CH.sub.3 2,3,4-Trlchlorphenyl m.p.: 110-112.d egree. C.; 251 O NCH.sub.3 NH CH.sub.3 CH.sub.3 3-Gromphenyl m.p.: 74-77.degree. C.; 252 NOCH.sub.3 NH CH.sub.3 CH.sub.3 4-Methylphenyl m.p.: 69-72.degr ee. C.; 253 NOCH.sub.3 NH CH.sub.3 CH.sub.3 4-Nitrophenyl m.p.: 134-137.degree. C.; 254 CHCH.sub.3 O CH.sub.3 CN 2-Ethoxy-prop-2-yl IR (film): 2982,1717,13 36,1255,1210,1192,1067,1037,1010 255 CHCH.sub.3 O CH.sub.3 CN 2-i-Propoxy-prop-2-yl IR (film): 2983,1718 ,1383,1370,1255,1173,1119,1109,1037,1002 256 CHCH.sub.3 O CH.sub.3 CN 2-n-Butoxy-prop-2-yl IR (film): 2957,1718, 13 35,1255,1176,1036,1010,759 257 CHCH.sub.3 O CH.sub.3 CN 2-1-Butoxy-prop-2-yl IR (film): 2956,1717, 13 35,1366,1255,1209,1176,1064,1037,1008 258 CHCH.sub.3 O CH.sub.3 CN Cyclopropyl .sup.1 H-NMR (CDCl.sub.3): .delta. = 0.9m, 1.6d, 2.3m, 3.67s, 5.15s, 7.05-7.4m 259 CHCH.sub.3 O CH.sub.3 CN 2-Ethylthio-prop-2-yl .sup.1 H-NMR (CDCl.sub.3): .delta. = 1.1t, 1.5s, 1.6d, 2.2q, 3.7s, 5.1s, 7.1-7.5m 260 CHCH.sub.3 O CH.sub.3 CN 2-1-Propylthio-pro-2-yl .sup.1 H-NMR (CDCl.sub.3): .delta. = 1.15s, 1.5s, 1.6d, 2.6m, 3.7s, 5.1s, 7.1-7.5m 261 CHCH.sub.3 O CH.sub.3 CN 2-Tetrahydropyranyl .sup.1 H-NMR (CDCl.sub.3): .delta. = 1.4-1.9m, 1.6d, 3.5m, 3.7s, 4.1m, 5.1s, 7.0-7.5m
TABLE IV__________________________________________________________________________ ##STR29##No. X Y R.sup.1 R.sup.3 R.sup.4 Data__________________________________________________________________________1 CHOCH.sub.3 O CH.sub.3 CH.sub.3 Phenyl2 CHOCH.sub.3 O CH.sub.3 CH.sub.3 3-Bromophenyl3 CHOCH.sub.3 O CH.sub.3 CH.sub.3 4-Phenoxyphenyl4 CHOCH.sub.3 O CH.sub.3 CH.sub.3 4-Cyclohexylphenyl5 NOCH.sub.3 O CH.sub.3 CH.sub.3 Phenyl6 NOCH.sub.3 O CH.sub.3 CH.sub.3 3-Bromophenyl oil; IR (film): 1727,1436,1312,1240,10327 NOCH.sub.3 O CH.sub.3 CH.sub.3 4-Phenoxyphenyl oil; IR (film): 1727,1489,1239,1031,6838 NOCH.sub.3 O CH.sub.3 CH.sub.3 4-Cyclohexylphenyl oil; IR (film): 2925,1728,1447,1239,1164,1077 ,10329 CHOCH.sub.3 O CH.sub.3 CN Iso-Propyl oil; IR (film): 2970,2220,1710,112710 CHOCH.sub.3 O CH.sub.3 CN 2-Methoxyprop-2-yl oil; IR (film): 2980,2220,1710,112711 CHOCH.sub.3 O CH.sub.3 CN 2-Methylthloprop-2-yl oil; IR (film): 2980,2220,1709,112712 CHOCH.sub.3 O CH.sub.3 CN 2-Tetrahydrofuranyl oil; IR (film): 2945,2850,2220,1709,112713 CHOCH.sub.3 O CH.sub.3 CN Phenyl oil; IR (film): 2940,2220,1709,1127,1030__________________________________________________________________________
TABLE V__________________________________________________________________________ ##STR30##No. R.sup.3 R.sup.4 Data__________________________________________________________________________1 H H2 H Methoxymethyl3 H Ethoxymethyl4 H n-Propoxymethyl5 H iso-Propoxymethyl6 H tert.-Butoxymethyl7 H 2-Methoxyprop-2-yl8 H 2-Ethoxyprop-2-yl9 H 2-n-Propoxyprop-2-yl10 H 2-iso-Propoxyprop-2-yl11 H 2-tert.-Butoxyprop-2-yl12 H Methylthiomethyl13 H tert.-Butylthiomethyl14 H 2-Methylthioprop-2-yl15 H 2-iso-Propylthioprop-2-yl16 H 2-tert.-Butylthioprop-2-yl17 H Methyl18 H Ethyl19 H n-Propyl20 H iso-Propyl21 H n-Butyl22 H iso-Butyl23 H sec.-Butyl24 H tert.-Butyl25 H n-Hexyl26 H n-Decyl27 H Cyclopropyl28 H Cyclohexyl29 H Phenylthiomethyl30 H 2-Phenylthiomethyl31 H 2-(2'-Chlorophonylthio)prop-2-yl32 H Ethynyl33 H 1-Propynyl34 H Methoxy35 H Ethoxy36 H n-Propoxy37 H iso-Propoxy38 H n-Butoxy39 H iso-Butoxy40 H sec.-Butoxy41 H tert.-Butoxy42 H Methylthio43 H Ethylthio44 H n-Propylthio45 H iso-Propylthio46 H n-Butylthio47 H iso-Butylthio48 H sec.-Butylthio49 H tert.-Butylthio50 H Benzylthio51 H Trifluoromethoxy52 H Cyano53 H Amino54 H Methylamino55 H Dimethylamino56 H Ethylamino57 H Diethylamino58 H Di-n-Propylamino59 H Di-iso-Propylamino60 H Di-n-Butylamino61 H Di-iso-Butylamino62 H Acetyl63 H Propion-1-yl64 H Butyr-1-yl65 H iso-Butyr-1-yl66 H Pivaloyl67 H Benzoyl68 H 4-Chlorobenzoyl69 H Benzylcarbonyl70 H Methoxycarbonyl71 H Ethoxycarbonyl72 H n-Propoxycarbonyl73 H iso-Propoxycarbonyl74 H n-Butoxycarbonyl75 H iso-Butoxycarbonyl76 H sec.-Butoxycarbonyl77 H tert.-Butoxycarbonyl78 H n-Hexoxycarbonyl79 H Phenoxycarbonyl80 H 4-Chlorphenoxycarbonyl81 H Benzyloxycarbonyl82 H Aminocarbonyl83 H Dimethylaminocarbonyl84 H Diethylaminocarbonyl85 H Di-iso-Propylaminocarbonyl86 H Phenylaminocarbonyl87 H N-Methyl-N-Phenylaminocarbonyl88 H Phenyl89 H 2-Fluorophenyl m.p.: 69-71.degree. C.;90 H 3-Fluorophenyl m.p.: 74-77.degree. C.;91 H 4-Fluorophenyl m.p.: 73-76.degree. C.; IR (KBr): 1699, 1278,1271,1256,122592 H Pentafluarophenyl m.p.: 94-96.degree. C.; IR (KBr): 1704, 1527,1494,113393 H 2-Chlorophenyl .sup.1 H-NMR(CDCl.sub.3 3): .delta. = 3.70s, 3.82s, 5.15s, 7.15-7.40m, 7.52m, 7.60s, 7.85m, 8.52s94 H 3-Chlorophenyl m.p.: 48-50.degree. C.;95 H 4-Chlorophenyl (v. Exaample 6)96 H Pentachlorophenyl97 H 2,3-Dichlorophenyl m.p.: 103-105.degree. C.;98 H 2,4-Dtchlorophenyl m.p.: 94-96.degree. C.;99 H 2,5-Dichlorophenyl100 H 2,6-Dichlorophenyl m.p.: 118-120.degree. C.;101 H 3,4-Dichlorophenyl m.p.: 82-84.degree. C.;102 H 3,5-Dichlorophenyl m.p.: 94-96.degree. C.;103 H 2,3,4-Trichlorophenyl104 H 2,3,5-Trichlorophenyl105 H 2,3,6-Trichlorophenyl106 H 2,4,5-Trichlorophenyl107 H 2,4,6-Trichlorophenyl108 H 3,4,5-Trichlorophenyl109 H 2,3,4,6-Tetrachlorophenyl110 H 2,3,5,6-Tetrachlorophenyl111 H 2-Bromophenyl m.p.: 85-87.degree. C.;112 H 3-Bromophenyl .sup.1 H-NMR (CDCl.sub.3): .delta. = 3.68s, 3.79s, 5.13, 7.15-7.54m, 7.59s 7.74s, 8.00s113 H 4-Bromophenyl m.p.: 131-134.degree. C.;114 H 2,4-Dibromophenyl115 H 3-Brom-4-fluorophenyl116 H 3-Brom-4-methoxyphenyl117 H 2-Iodophenyl118 H 3-Iodophenyl119 H 4-Iodophenyl120 H 2-Chloro-4-fluorophenyl m.p.: 112-115.degree. C.;121 H 2-Chloro-5-fluorophenyl122 H 2-Chloro-6-fluorophenyl m.p.: 80-82.degree. C.;123 H 2-Chloro-4-bromophenyl124 H 2-Bromo-4-chlorophenyl125 H 2-Bromo-4-fluorophenyl126 H 3-Bromo-4-chlorophenyl127 H 3-Chloro-4-fluorophenyl128 H 3-Fluoro-4-chlorophenyl129 H 2-Cyanophenyl130 H 3-Cyanophenyl131 H 4-Cyanophenyl132 H 2-Nitrophenyl133 H 3-Nitrophenyl134 H 4-Nitrophenyl m.p.: 147-155.degree. C.;135 H 2-methylphenyl m.p.: 57-59.degree. C.;136 H 3-Methylphenyl m.p.: 54-56.degree. C.;137 H 4-Methylphenyl m.p.: 86-88.degree. C.;138 H 2,4-Dimethylphenyl m.p.: 75-77.degree. C.;139 H 2,6-Dimethylphenyl140 H 3,4-Dimethylphenyl141 H 3,5-Dimethylphenyl142 H 2,3,4-Trimethylphenyl143 H 2,3,5-Trimethylphenyl144 H 2,3,6-Trimethylphenyl145 H 2,4,5-Trimethylphenyl146 H 2,4,6-Trimethylphenyl147 H 3,4,5-Trimethylphenyl148 H Pentamethylphenyl149 H 2-Ethylphenyl150 H 3-Ethylphenyl151 H 4-Ethylphenyl152 H 3,5-Diethylphenyl153 H 2-n-Propylphenyl154 H 3-n-Propylphenyl155 H 4-n-Propylphenyl156 H 2-iso-propylphenyl157 H 3-iso-Propylphenyl158 H 4-iso-Propylphenyl159 H 2,4-Di-iso-Propylphenyl160 H 3,5-Di-iso-Propylphenyl161 H 4-n-Butylphenyl162 H 4-sec.-Butylphenyl163 H 4-iso-Butylphenyl164 H 4-tert.-Butylphenyl m.p.: 71-73.degree. C.165 H 3-tert.-Butylphenyl166 H 2-tert.-Butylphenyl167 H 2,4-Di-tert.-Butylphenyl168 H 3,5-Di-tert.-Butylphenyl169 H 4-n-Hexylphenyl170 H 4-n-Dodecylphenyl171 H 2-Methyl-4-tert.-Butylphenyl172 H 2-Methyl-6-tert.-outylphenyl173 H 2-Methyl-4-iso-Propylphenyl174 H 2-Methy1-4-cyclohexylphenyl175 H 2-Methyl-4-phenylphenyl176 H 2-Methyl-4-benzylphenyl177 H 2-Methyl-4-phenoxyphenyl178 H 2-Methyl-4-benzyloxyphenyl179 H 2-Methyl-3-chlorophenyl180 H 2-Methyl-4-chlorophenyl181 H 2-Methyl-5-chlorophenyl182 H 2-Methyl-6-chlorophenyl183 H 2-Methyl-4-fluorophenyl184 H 2-Methyl-3-bromophenyl185 H 2-Methyl-4-bromophenyl186 H 2-Methyl-3-methoxyphenyl187 H 2-Methyl-4-methoxyphenyl188 H 2-Methyl-5-methoxyphenyl189 H 2-Methyl-6-methoxyphenyl190 H 2-Methyl-4-iso-Propoxyphenyl191 H 2-Methyl-2,5-dimethoxyphenyl192 H 2-Methoxyphenyl m.p.: 52-54.degree. C.193 H 3-Methoxyphenyl .sup.1 H-NMR (CDCl.sub.3): .delta. = 3.65s, 3.76s, 3.80s, 5.12s, 6.88-7.54m, 7.58s, 8.05s194 H 4-Methoxyphenyl m.p.: 61-63.degree. C.195 H 2,3-Dimethoxyphenyl196 H 2,4-Dimethoxyphenyl m.p.: 70-72.degree. C.197 H 2,5-Dimethoxyphenyl198 H 2,6-Dimethoxyphenyl199 H 3,4-Dimethoxyphenyl200 H 3,5-Dimethoxyphenyl m.p.: 79-82.degree. C.201 H 3,6-Dimethoxyphenyl202 H 2,3,4-Trimethoxyphenyl203 H 2,3,5-Trimethoxyphenyl204 H 2,3,6-Trimethoxyphenyl205 H 2,4,5-Trimethoxyphenyl206 H 2,4,6-Trimethoxyphenyl207 H 3,4,5-Trimethoxyphenyl208 H 2-Ethoxyphenyl209 H 3-Ethoxyphenyl .sup.1 H-NMR (CDCl.sub.3): .delta. = 1.39t, 3.67s, 3.80s, 4.02q, 5.12s, 6.87-7.54m, 7.58s, 8.05s210 H 4-Ethoxyphenyl m.p.: 93-94.degree. C.211 H 2-iso-Propoxyphenyl212 H 3-iso-Propoxyphenyl213 H 4-iso-Propoxyphenyl214 H 3-tert.-Butoxyphenyl215 H 4-tert.-Butoxyphenyl .sup.1 H-NMR (CDCl.sub.3): .delta. = 1.36s, 3.68s, 3.78s, 5.09s, 6.94-7.53m, 7.58s, 8.07s216 H 2-Trifluoromethoxyphenyl217 H 3-Trifluoromethoxyphenyl218 H 4-Trtfluorowthoxyphenyl219 H 3-(1',1',2',2'-Tetrafluoro)ethoxyphenyl220 H 4-(1',1',2',2'-Tetrafluoro)ethoxyphenyl221 H 2-Chloromethylphenyl222 H 3-Chloromethylphenyl223 H 4-Chloromethylphenyl224 H 2-Trifluoromethylphenyl m.p.: 75-77.degree. C.225 H 3-Trifluoromethylphenyl226 H 4-Trifluoromethylphenyl m.p.: 111-114.degree. C.227 H 2-(Methoxyiminomethyl)phenyl228 H 3-(Methoxyiminomethyl)phenyl229 H 4-(Methoxyiminomethyl)phenyl230 H 2-(Ethoxyiminomethyl)phenyl231 H 3-(Ethoxyininomethyl)phenyl232 H 4-(Ethoxyiminomthyl)phenyl233 H 2-(n-Propoxyiminomethyl)phenyl234 H 3-(n-Propoxyiminomethyl)phenyl235 H 4-(n-Propoxyiminomethyl)phenyl236 H 2-(iso-Propoxyiminomethyl)phenyl237 H 3-(iso-Propoxyiminomethyl)phenyl238 H 4-(iso-Propoxyiminomethyl)phenyl239 H 2-(n-Butoxyiminomethyl)phenyl240 H 3-(n-Butoxyiminomethyl)phenyl241 H 4-(n-Butoxyiminomethyl)phenyl242 H 2-(iso-Butoxyiminomethyl)phenyl243 H 3-(iso-Butoxytminomethyl)phenyl244 H 4-(iso-Butoxyiminomethyl)phenyl245 H Z-(tert.-Butoxyiminamethyl)phenyl246 H 3-(tert.-Butoxyiminomethyl)phenyl247 H 4-(tert.-Butoxyiminomethyl)phenyl248 H 2-(n-Pentoxyiminomethyl)phenyl249 H 3-(n-Pentoxyiminomethyl)phenyl250 H 4-(n-Pentoxyiminomethyl)phenyl251 H 2-(n-Hexoxyiminomethyl)phenyl252 H 3-(n-Hexoxyiminomethyl)phenyl253 H 4-(n-Hexoxyiminomethyl)phenyl254 H 2-(Allyloxyiminomethyl)phenyl255 H 3-(Allyloxyiminomethyl)phenyl256 H 4-(Allyloxyiminomethyl)phenyl257 H 2-(Benzyloxyiminomethyl)phenyl258 H 3-(Benzyloxyiminomethyl)phenyl259 H 4-(Benzyloxyiminamethyl)phenyl260 H 2-(Methoxyimino-1'-ethyl)phenyl261 H 3-(Methoxyimino-1'-ethyl)phenyl262 H 4-(Methoxytmino-1'-ethyl)phenyl263 H 2-(Ethoxyimino-1'-ethyl)phenyl264 H 3-(Ethoxyimino-1'-ethyl)phenyl265 H 4-(Ethoxyimino-1'-ethyl)phenyl266 H 2-(n-Propoxyimino-1'-ethyl)phenyl267 H 3-(n-Propoxyimino-1'-ethyl)phenyl268 H 4-(n-Propoxyimino-1'-ethyl)phenyl269 H 2-(n-Butoxyamino-1'-ethyl)phenyl270 H 3-(n-Butoxyanino-1'-ethyl)phenyl271 H 4-(n-Butoxyamino-1'-ethyl)phenyl272 H 2-(n-Pentoxyimino-1'-ethyl)phenyl273 H 3-(n-Pentoxyimino-1'-ethyl)phenyl274 H 4-(n-Pentoxyimino-1'-ethyl)phenyl275 H 2-(n-Hexoxyimino-1'-ethyl)phenyl276 H 3-(n-Hexoxyimino-1'-ethyl)phenyl277 H 4-(n-Hexoxyimino-1'-ethyl)phenyl278 H 2-(Allyloxyimino-1'-ethyl)phenyl279 H 3-(Allyloxyimino-1'-ethyl)phenyl280 H 4-(Allyloxyimino-1'-ethyl)phenyl281 H 2-(Benzyloxyimino-1'-ethyl)phenyl282 H 3-(Benzyloxyimino-1'-ethyl)phenyl283 H 4-(Benzyloxyimino-1'-ethyl)phenyl284 H 2-Phenylphenyl285 H 3-Phenylphenyl286 H 4-Phenylphenyl m.p.: 94-96.degree. C.287 H 2-Phenoxyphenyl288 H 3-Phenoxyphenyl289 H 4-Phenoxyphenyl290 H 2-Benzyloxyphenyl291 H 3-Benzyloxyphenyl292 H 4-Benzyloxyphenyl m.p.: 94-96.degree. C.293 H 4-(Imidazol-1'-yl)phenyl294 H 4-(Piperazin-1'-yl)phenyl295 H 4-(Morpholin-1'-yl)phenyl296 H 4-(Piperidin-1'-yl)phenyl297 H 4-(Pyridyl-2'-oxy)phenyl298 H 2-Cyclopropylphenyl299 H 3-Cyclopropylphenyl300 H 4-Cyclopropylphenyl301 H 3-Cyclohexylphenyl302 H 4-Cyclohexylphenyl303 H 4-Oxiranylphenyl304 H 4-(1',3'-Dioxan-2'-yl)phenyl305 H 4-(Tetrahydropyran-2-yloxy)phenyl306 H 1-Naphthyl307 H 2-Naphthyl oil; IR (film): 1707, 1633,1257,1129,110308 H 9-Anthryl309 H 1-Naphtoxy310 H 2-Naphtoxy311 H 9-Anthroxy312 H Phenoxy313 H 2-Chlorophenoxy314 H 3-Chlorophenoxy315 H 4-Chlorophenoxy316 H 4-Methylphenoxy317 H 4-tert.-Butylphenoxy318 H 4-Methoxyphenoxy319 H 4-Ethoxyphenoxy320 H 4-tert.-Butoxyphenoxy321 H Phenylthio322 H 2-Chlorophenylthio323 H 4-Chlorophenylthio324 H Benzyl325 H 2-Methylbenzyl326 H 3-Methylbenzyl327 H 4-Methylbenyzl328 H 4-tert.-Butylbenzyl329 H 2-Chlorobenzyl330 H 3-Chlorobenzyl331 H 4-Chlorobenzyl332 H 2,4-Dichlorobenzyl333 H 2,6-Dichlorobenzyl334 H 2,4,6-Trichlorobenzyl335 H 2-Trifluoromethylbenzyl336 H 3-Trtfluaromethylbenzyl337 H 4-Trifluoromethylbenzyl338 H 2-Methoxybenzyl339 H 4-Methoxybenzyl340 H 4-tert.-Butoxybenzyl341 H 4-Phenoxybenzyl342 H 1-Phenethyl343 H 2-Phenethyl344 H 1-Phenylpropyl345 H 2-Phenylpropyl346 H 3-Phenylpropyl347 H 2-Methyl-2-phenylpropyl348 H 2-Methyl-3-phenylpropyl349 H 4-Phenylbutyl350 H 2-Phenyl-1-ethenyl351 H 1-Phenyl-1-ethenyl352 H 1-Phenyl-1-propenyl353 H 1-Phenyl-1-propen-2-yl354 H 2,2-Diphenylethenyl355 H Phenoxymethyl356 H 2-Pyridyl357 H 3-Pyridyl358 H 4-Pyridyl359 H 2,6-Pyrimidinyl360 H 1,5-Pyrimidinyl361 H 2-Thienyl362 H 3-Thienyl363 H 2-Furyl364 H 3-Furyl365 H 1-Pyrrolyl366 H 1-Imidazolyl367 H 1,2,4-Triazolyl368 H 1,3,4-Triazolyl369 H 4-Thiazolyl370 H 2-Senzothiozolyl371 H 2-Pyridyloxy372 H 2-Pyrimidinyloxy373 H 2-Pyridylthio374 H 2-Pyrimidinylthio375 H 2-Benzothiozolylthio376 H Phenylthiomethyl377 H 2-Pyridylmethyl378 H 3-Pyridylmethyl379 H Furfuryloxy380 H Thienylmthoxy381 H 3-Isoxazolylmethoxy382 4 2-Oxazolylmethoxy383 4 2-Pyridylmethoxy384 H 2'-Furyl-2-ethenyl385 H 2'-Thienyl-2-ethenyl386 H 3'-Pyridyl-2-ethenyl387 H Oxiranyl388 H 1-Aziridinyl389 H 1-Azetidinyl390 H 1-Pyrrolidinyl391 H 2-Tetrahydrofuryl392 H 2-Tetrahydropyranyl393 H 3-Tetrahydropyranyl394 H 1-Piperidinyl395 H 1-Morpholinyl396 H i-Piperazinyl397 H 1,3-Dioxan-2-yl398 H 3-Tetrahydrothiopyranyl399 H 2-Dihydropyranyloxy400 H 2-Tetrahydropyranyloxy401 H CF.sub.3402 H 2-Fluoroethyl403 H 2,2,2-Trifluoroethyl404 m Pentafluoroethyl405 H Chloromethyl406 H Dichloromethyl407 H Trichloromethyl408 H 2-Chloroethyl409 H 2,2,2-Trichloroethyl410 H Pentachloroothyl411 H Cyclopropyl412 H Cyclobutyl413 H cyclopentyl414 H Cyclohexyl415 H 1-Methylcyclopropyl416 H 2,2-Dimethylcyclopropyl417 H 1-Methylcyclohexyl418 H 2,2-Difluorocyclopropyl419 H 2,2-Dichloracyclopropyl420 H 2,2-Dibromocyclopropyl421 H 2,2-Dichloro-3-Methylcyclopropyl422 H 2,2,3,3-Tetrafluorocyclobutyl423 H Ethenyl424 H 1-Propenyl425 H 2-Methyl-1-propenyl426 H 4-Methylpent-3-en-1-yl427 H 2-Propenyl428 H 2-Butenyl429 H 1-Methyl-2-propenyl430 H 3-Methyl-2-butenyl431 H 2,2-Difluoroethenyl432 H 2,2-Dichloroethenyl433 H 3,3,3-Trifluoropropenyl434 H 3,3,3-Trichloropropenyl435 H 3-Chloro-2-propenyl436 H Cyclopent-1-enyl437 H Cyclopentadienyl438 H Cyclohex-1-enyl439 H Pentafluorocyclopentadienyl440 H Pentachlorocyclopentadienyl441 H 4-Dimethylaminaphenyl m.p.: 90-92.degree. C.442 H 4-n-Butoxyphenyl m.p.: 79-82.degree. C.__________________________________________________________________________
TABLE VI__________________________________________________________________________ ##STR31##No. R.sup.3 R.sup.4 Data__________________________________________________________________________1 H H m.p.: 94-95.degree. C.2 H Methoxymethyl3 H Ethoxymethyl4 H n-Propoxymethyl5 H iso-Propoxymethyl6 H tert.-Butoxymethyl7 H 2-Methoxyprop-2-yl8 H 2-Ethoxyprop-2-yl9 H 2-n-Propoxyprop-2-yl10 H 2-iso-Propoxyprop-2-yl11 H 2-tert.-Butoxyprop-2-yl12 H Methylthiomethyl13 H tert.-Butylthiomethyl14 H 2-methylthioprop-2-yl15 H 2-iso-Propylthioprop-2-yl16 H 2-tert.-Butylthioprop-2-yl17 H Methyl18 H Ethyl19 H n-Propyl20 H iso-Propyl21 H n-Butyl22 H iso-Butyl23 H sec.-Butyl24 H tert.-Butyl25 H n-Hexyl26 H n-Decyl27 H Cyclopropyl28 H Cyclohexyl29 H Phenylthiomethyl30 H 2-Phenylthiomethyl31 H 2-(2'-Chlorophenylthio)prop-2-yl32 H Ethynyl33 H 1-Propynyl34 H Methoxy35 H Ethoxy36 H n-Propoxy37 H iso-Propoxy38 H n-Butoxy39 H iso-Butoxy40 H sec.-Butoxy41 H tert.-Butoxy42 H Methylthio43 H Ethylthio44 H n-Propylthio45 H iso-Propylthio46 H n-Butylthio47 H iso-Butylthio48 H sec.-Butylthio49 H tert.-Butylthio50 H Benzylthio51 H Trifluoromethoxy52 H Cyano53 H Amino54 H Methylamino55 H Dimethylamino56 H Ethylamino57 H Diethylamino58 H Di-n-Propylanino59 H Di-iso-Propylamino60 H Di-n-Butylamino61 H Di-iso-Butylamino62 H Acetyl63 H Propion-1-yl64 H Butyr-1-yl65 H iso-Butyr-1-yl66 H Pivaloyl67 H Benzoyl68 H 4-Chlorobenzoyl69 H Benzylcarbonyl70 H Methoxycarbonyl71 H Ethoxycarbonyl72 H n-Propoxycarbonyl73 H iso-Propoxycarbonyl74 H n-Butoxycarbonyl75 H iso-Butoxycarbonyl76 H sec.-Butoxycarbonyl77 H tert.-Butoxycarbonyl78 H n-Hexoxycarbonyl79 H Phenoxycarbonyl80 H 4-Chlorophenoxycarbonyl81 H Benzyloxycarbonyl82 H Aminocarbonyl83 H Dimethylaminocarbonyl84 H Diethylaminocarbonyl85 H Di-iso-Propylaminocarbonyl86 H Phenylaminocarbonyl87 H N-Methyl-N-Phenylaminocarbonyl88 H Phenyl m.p.: 92-95.degree. C.89 H 2-Fluorophenyl m.p.: 92-95.degree. C.90 H 3-Fluorophenyl m.p.: 58-60.degree. C.91 H 4-Fluorophenyl m.p.: 110-111.degree. C.92 H Pentafluorophenyl m.p.: 118-120.degree. C.93 H 2-Chlorophenyl .sup.1 H-NMR(CDCl.sub.3): .delta. = 3.70s, 3.82s, 5.15s, 7.15-7.40m, 7.52m, 7.60s, 7.85m, 8.52s94 H 3-Chlorophenyl m.p.: 58-60.degree. C.95 H 4-Chlorophenyl m.p.: 146-148.degree. C.96 H Pentachlorophenyl97 H 2,3-Dichlorophenyl m.p.: 95-97.degree. C.98 H 2,4-Dichlorophenyl m.p.: 58-62.degree. C.99 H 2,5-Dichlorophenyl100 H 2,6-Dichlorophenyl m.p.: 136-140.degree. C.101 H 3,4-Dichlorophenyl m.p.: 94-97.degree. C.102 N 3,5-Dichlorophenyl m.p.: 88-91.degree. C.103 H 2,3,4-Trichlorophenyl104 N 2,3,5-Trichlorophenyl105 H 2,3,6-Trichlorophenyl106 H 2,4,5-Trichlorophenyl107 H 2,4,6-Trichlorophenyl108 H 3,4,5-Trichlorophenyl109 H 2,3,4,6-Tetrachlorophenyl110 H 2,3,5,6-Tetrachlorophenyl111 H 2-Bromophenyl m.p.: 91-94.degree. C.112 H 3-Bromophenyl m.p.: 63-64.degree. C.113 H 4-Bromophenyl m.p.: 145-147.degree. C.114 H 2,4-Dibromophenyl115 H 3-Bromo-4-Fluorophenyl116 H 3-Bromo-4-Methoxyphenyl117 H 2-Iodophenyl118 H 3-Iodophenyl119 H 4-Iodophenyl120 H 2-Chloro-4-Fluorophenyl m.p.: 90-93.degree. C.121 H 2-Chloro-5-Fluorophenyl122 H 2-Chloro-6-Fluorophenyl m.p.: 111-113.degree. C.123 H 2-Chloro-4-Bromophenyl124 H 2-Bromo-4-Chlorophenyl125 H 2-Bromo-4-Fluorophenyl126 H 3-Bromo-4-Chlorophenyl127 H 3-Chloro-4-Fluorophenyl128 H 3-Fluoro-4-Chlorophenyl129 H 2-Cyanophenyl130 H 3-Cyanophenyl131 H 4-Cyanophenyl132 H 2-Nitrophenyl133 H 3-Nitrophenyl134 H 4-Nitrophenyl m.p.: 142-146.degree. C.135 H 2-Methylphenyl m.p.: 58-60.degree. C.136 H 3-Methylphonyl m.p.: 70-72.degree. C.137 H 4-Methylphenyl m.p.: 99-102.degree. C.138 H 2,4-Dimethylphenyl m.p.: 54-56.degree. C.139 H 2,6-Dimethylphenyl140 H 3,4-Dimethylphenyl141 H 3,5-Dimethylphenyl142 H 2,3,4-Trimethylphenyl143 H 2,3,5-Trimethylphenyl144 H 2,3,6-Trimethylphenyl145 H 2,4,5-Trimethylphenyl146 H 2,4,6-Trimethylphenyl147 H 3,4,5-Trimethylphenyl148 H Pentamethylphenyl149 H 2-Ethylphenyl150 H 3-Ethylphenyl151 H 4-Ethylphenyl152 H 3,5-Diethylphonyl153 H 2-n-Propylphenyl154 H 3-n-Propylphenyl155 H 4-n-Propylphenyl156 H 2-iso-Propylphenyl157 H 3-iso-Propylphenyl158 H 4-iso-Propylphenyl159 H 2,4-Di-iso-Propylphenyl160 H 3,5-Di-iso-Propylphenyl161 H 4-n-Butylphenyl162 H 4-sec.-Butylphenyl163 H 4-iso-Butylphenyl164 H 4-tert.-Butylphenyl m.p.: 82-84.degree. C.165 H 3-tert.-Butylphenyl166 H 2-tert.-Butylphenyl167 H 2,4-Di-tert.-Butylphenyl168 H 3,5-Di-tert.-Butylphenyl169 H 4-n-Hexylphenyl170 H 4-n-Dodecylphenyl171 H 2-Methyl-4-tert.-Butylphenyl172 H 2-Methyl-6-tert.-Butylphenyl173 H 2-Methyl-4-iso-Propylphenyl174 H 2-Methyl-4-Cyclohexylphenyl175 H 2-Methyl-4-Phenylphenyl176 H 2-Methyl-4-Benzylphenyl177 H 2-Methyl-4-Phenoxyphenyl178 H 2-Methyl-4-Benzyloxyphenyl179 H 2-Methyl-3-Chlorophenyl180 H 2-Methyl-4-Chlorophenyl181 H 2-Methyl-5-Chlorophenyl182 H 2-Methyl-6-Chlorophenyl183 H 2-Methyl-4-Fluorophenyl184 H 2-Methyl-3-Bromophenyl185 H 2-Methyl-4-Bromophenyl186 H 2-Methyl-3-Methoxyphenyl187 H 2-Methyl-4-Methoxyphenyl188 H 2-Methyl-5-Methoxyphenyl189 H 2-Methyl-6-Methoxyphenyl190 H 2-Methyl-4-iso-Propoxyphenyl191 H 2-Methyl-2,5-Dimethoxyphenyl192 H 2-Methoxyphenyl m.p.: 65-68.degree. C.193 H 3-Methoxyphenyl m.p.: 83-84.degree. C.194 H 4-Methoxyphenyl m.p.: 88-90.degree. C.195 H 2,3-Dimethoxyphenyl196 H 2,4-Dimethoxyphenyl m.p.: 90-93.degree. C.197 H 2,5-Dimethoxyphenyl198 H 2,6-Dimethoxyphenyl199 H 3,4-Dimethoxyphenyl m.p.: 70-72.degree. C.200 H 3,5-Dimethoxyphenyl m.p.: 97-99.degree. C.201 H 3,6-Dimethoxyphenyl202 H 2,3,4-Trimethoxyphenyl203 H 2,3,5-Trimethoxyphemyl204 H 2,3,6-Trimethoxyphenyl205 H 2,4,5-Trimethoxyphenyl206 H 2,4,6-Trimethoxyphenyl207 H 3,4,5-Trimethoxyphenyl m.p.: 105-109.degree. C.208 H 2-Ethoxyphenyl209 H 3-Ethoxyphenyl m.p.: 90-92.degree. C.210 H 4-Ethoxyphenyl m.p.: 97-98.degree. C.211 H 2-iso-Propoxyphenyl212 H 3-iso-Propoxyphenyl213 H 4-iso-Propoxyphenyl214 H 3-tert.-Butoxyphenyl215 H 4-tert.-Butoxyphenyl m.p.: 78-83.degree. C.216 H 2-Trifluoromethoxyphenyl217 H 3-Trifluoromethoxyphenyl218 H 4-Trifluoromethoxyphenyl219 H 3-(1',1',2',2'-Tetrafluoro)ethoxyphenyl220 H 4-(1',1',2',2'-Tetrafluoro)ethoxyphenyl221 H 2-Chloromethylphenyl222 H 3-Chloromethylphenyl223 H 4-Chloromethylphenyl224 H 2-Trifluoromethylphenyl m.p.: 58-60.degree. C.225 H 3-Trifluoromethylphenyl m.p.: 74-77.degree. C.226 H 4-Trifluoromethylphenyl m.p.: 120-122.degree. C.227 H 2-(Methoxyiminomethyl)phenyl228 H 3-(Methoxyiminomethyl)phenyl229 H 4-(Methoxyiminomethyl)phenyl230 H 2-(Ethoxyiminomethyl)phenyl231 H 3-(Ethoxyiminomethyl)phenyl232 H 4-(Ethoxyiminomethyl)phenyl233 H 2-(n-Propoxyiminomethyl)phenyl234 H 3-(n-Propoxyiminomethyl)phenyl235 H 4-(n-Propoxyiminomethyl)phenyl236 H 2-(iso-Propoxyiminomethyl)phenyl237 H 3-(iso-Propoxyiminomethyl)phenyl238 H 4-(iso-Propoxyiminomethyl)phenyl239 H 2-(n-Butoxyiminomethyl)phenyl240 H 3-(n-Butoxyiminomethyl)phenyl241 H 4-(n-Butoxyiminomethyl)phenyl242 H 2-(iso-Butoxyiminomethyl)phenyl243 H 3-(iso-Butoxyiminomethyl)phenyl244 H 4-(iso-Butoxyiminomethyl)phenyl245 H 2-(tert.-Butoxyiminomethyl)phenyl246 H 3-(tert.-Butoxyiminomethyl)phenyl247 H 4-(tert.-Butoxyiminomethyl)phonyl248 H 2-(n-Pentoxyiminomethyl)phenyl249 H 3-(n-Pentoxyininomethyl)phenyl250 H 4-(n-PentoxyiminoMethyl)phenyl251 H 2-(n-Hexoxyiminomethyl)phenyl252 H 3-(n-Hexoxyiminomethyl)phenyl253 H 4-(n-Hexoxyiminomethyl)phenyl254 H 2-(Allyloxyiminomethyl)phenyl255 H 3-(Allyloxyiminomethyl)phenyl256 H 4-(Allyloxyiminomethyl)phenyl257 H 2-(Benzyloxytainomethyl)phenyl258 H 3-(Benzyloxyininomethyl)phenyl259 H 4-(Benzyloxyiminomethyl)phenyl260 H 2-(Methoxyimino-1'-ethyl)phenyl261 H 3-(Methoxyimino-1'-ethyl)phenyl262 H 4-(Methoxyimino-1'-ethyl)phenyl263 H 2-(Ethoxyimino-1'-ethyl)phenyl264 H 3-(Ethoxyimino-1'-ethyl)phenyl265 H 4-(Ethoxyimino-1'-ethyl)phenyl266 H 2-(n-Propoxyimino-1'-ethyl)phenyl267 H 3-(n-Propoxyimino-1'-ethyl)phenyl268 H 4-(n-Propoxyimino-1'-ethyl)phenyl269 H 2-(n-Butoxyamino-1'-ethyl)phenyl270 H 3-(n-Butoxyanino-1'-ethyl)phenyl271 H 4-(n-Butoxyamino-1'-ethyl)phenyl272 H 2-(n-Pentoxyimino-1'-ethyl)phenyl273 H 3-(n-Pentoxyimino-1'-ethyl)phenyl274 H 4-(n-Pentoxyimino-1'-ethyl)phenyl275 H 2-(n-Hexoxyimino-1'-ethyl)phenyl276 H 3-(n-Hexoxyimino-1'-ethyl)phenyl277 H 4-(n-Hexoxyimino-1'-ethyl)phenyl278 H 2-(Allyloxyimino-1'-ethyl)phenyl279 H 3-(Allyloxyimino-1'-ethyl)phenyl280 H 4-(Allyloxyimino-1'-ethyl)phenyl281 H 2-(Benzyloxyimino-1'-ethyl)phenyl282 H 3-(Benzyloxyimino-1'-ethyl)phenyl283 H 4-(Benzyloxyimino-1'-ethyl)phenyl284 H 2-Phenylphenyl285 H 3-Phenylphenyl286 H 4-Phenylphenyl m.p.: 100-102.degree. C.287 H 2-Phenoxyphenyl288 H 3-Phenoxyphenyl IR (film): 1728,1489, 1247,1214,1070,1020289 H 4-Phenoxyphenyl m.p.: 85-87.degree. C.290 H 2-Benzyloxyphenyl m.p.: 83-85.degree. C.291 H 3-Benzyloxyphenyl m.p.: 66-68.degree. C.292 H 4-Benzyloxyphenyl m.p.: 104-106.degree. C.293 H 4-(Imidazol-1'-yl)phenyl294 H 4-(Piperazin-1'-yl)phenyl295 H 4-(Morpholin-1'-yl)phenyl296 H 4-(Piperidin-1'-yl)phenyl297 H 4-(Pyridyl-2'-oxy)phenyl298 H 2-Cyclopropylphenyl299 H 3-Cyclopropylphenyl300 H 4-Cyclopropylphenyl301 H 3-Cyclohexylphenyl302 H 4-Cyclohexylphenyl303 H 4-Oxiranylphenyl304 H 4-(1',3'-Dioxan-2'-yl)phenyl305 H 4-(Tetrahydropyran-2-yloxy)phenyl306 H 1-Naphthyl m.p.: 70-73.degree. C.307 H 2-Naphthyl m.p.: 125-126.degree. C.308 H 9-Anthryl309 H 1-Naphthoxy310 H 2-Naphthoxy311 H 9-Anthroxy312 H Phenoxy313 H 2-Chlorophenoxy314 H 3-Chlorophenoxy315 H 4-Chlorophenoxy316 H 4-Methylphenoxy317 H 4-tert.-Butylphenoxy318 H 4-Methoxyphenoxy319 H 4-Ethoxyphenoxy320 H 4-tert.-Butoxyphenoxy321 H Phenylthio322 H 2-Chlorophenylthio323 H 4-Chlorophenylthio324 H Benzyl325 H 2-Methylbenzyl326 H 3-Methylbenzyl327 H 4-Methylbenyzl328 H 4-tert.-Butylbenzyl329 H 2-Chlorobenzyl330 H 3-Chlorobenzyl331 H 4-Chlorobenzyl332 H 2,4-Dichlorobenzyl333 H 2,6-Dichlorobenzyl334 H 2,4,6-Trichlorobenzyl335 H 2-Trifluoromethylbenzyl336 H 3-Trifluoromethylbenzyl337 H 4-Trifluoromethylbenzyl338 H 2-Methoxybenzyl339 H 4-Methoxybenzyl340 H 4-tert.-Butoxybenzyl341 H 4-Phenoxybenzyl342 H 1-Phenethyl343 H 2-Phenethyl344 H 1-Phenylpropyl345 H 2-Phenylpropyl346 H 3-Phenylpropyl347 H 2-Methyl-2-phenylpropyl348 H 2-Methyl-3-phenylpropyl349 H 4-Phenylbutyl350 H 2-Phenyl-1-ethenyl351 H 1-Phenyl-1-ethenyl352 H 1-Phenyl-1-propenyl353 H 1-Phenyl-1-propen-2-yl354 H 2,2-Diphenylethenyl355 H Phenoxymethyl356 H 2-Pyridyl357 H 3-Pyridyl358 H 4-Pyridyl359 H 2,6-Pyrimidinyl360 H 1,5-Pyrimidinyl361 H 2-Thienyl362 H 3-Thienyl363 H 2-Furyl364 H 3-Furyl365 H 1-Pyrrolyl366 H 1-Imidazolyl367 H 1,2,4-Triazolyl368 H 1,3,4-Triazolyl369 H 4-Thiazolyl370 H 2-Benzothiazolyl371 H 2-Pyridyloxy372 H 2-Pyrimidinyloxy373 H 2-Pyridylthio374 H 2-Pyrimidinylthio375 H 2-Benzothiazolylthio376 H Phenylthiomethyl377 H 2-Pyridylmethyl378 H 3-Pyridylmethyl379 H Furfuryloxy380 H Thienylmethoxy381 H 3-Isoxazolylmethoxy382 H 2-Oxazolylmethoxy383 H 2-Pyridylmethoxy384 H 2'-Furyl-2-ethenyl385 H 2'-Thienyl-2-ethenyl386 H 3'-Pyridyl-2-ethenyl387 H Oxiranyl388 H 1-Aziridinyl389 H 1-Azetidinyl390 H I-Pyrrolidinyl391 H 2-Tetrahydrofuryl392 H 2-Tetrahydropyranyl393 H 3-Tetrahydropyranyl394 H 1-Piperidinyl395 H 1-Morpholinyl396 H 1-Piperazinyl397 H 1,3-Dioxan-2-yl398 H 3-Tetrahydrothiopyranyl399 H 2-Dihydropyranyloxy400 H 2-Tetrahydropyranyloxy401 H CF.sub.3402 H 2-Fluoroethyl403 H 2,2,2-Trifluoroethyl404 H Pentafluoroethyl405 H Chloromethyl406 H Dichloromethyl407 H Trichloromethyl408 H 2-Chloroethyl409 H 2,2,2-Trichloroethyl410 H Pentachloroethyl411 H Cyclopropyl412 H Cyclobutyl413 H Cyclopentyl414 H Cyclohexyl415 H 1-Methylcyclopropyl416 H 2,2-Dimethylcyclopropyl417 H 1-Methylcyclohexyl418 H 2,2-Difluorocyclopropyl419 H 2,2-Dichlorocyclopropyl420 H 2,2-Dibromocyclopropyl421 H 2,2-Dichloro-3-methylcyclopropyl422 H 2,2,3,3-Tetrafluorocyclobutyl423 H Ethenyl424 H 1-Propenyl425 H 2-Methyl-1-propenyl426 H 4-Methylpent-3-en-1-yl427 H 2-Propenyl428 H 2-Butenyl429 H 1-Methyl-2-propenyl430 H 3-Methyl-2-butenyl431 H 2,2-Difluoroethenyl432 H 2,2-Dichloroethenyl433 H 3,3,3-Trifluoropropenyl434 H 3,3,3-Trichloropropenyl435 H 3-Chloro-2-propenyl436 H Cyclopent-1-enyl437 H Cyclopentadienyl438 H Cyclohex-1-enyl439 H Pentafluorocyclopentadienyl440 H Pentachlorocyclopentadienyl441 H 4-Dimethylaminophenyl m.p.: 70-71.degree. C.442 H 4-Allyloxyphenyl m.p.: 81-83.degree. C.443 H Diphenylmethyl m.p.: 66-68.degree. C.444 H Dimethylbenzyl .sup.1 H-NMR (CDCl.sub.3): .delta. = 1.45s 3.78s, 4.03s, 5.00s 7.17-7.41m__________________________________________________________________________
TABLE VII______________________________________ ##STR32##No. R.sub.n.sup.8 Data______________________________________1 H m.p. 156-158.degree. C.2 3-Fluoro3 4-Fluoro4 3-Chloro5 4-Chloro6 3-Bromo7 4-Bromo8 3-Iodo9 4-Iodo10 3,4-Dichloro11 3,5-Dichloro12 3,6-Dichloro13 4,5-Dichloro14 3,4,5-Trichloro15 3,4,6-Trichloro16 3,4,5,6-Tetrachloro17 3,4,5,6-Tetrafluoro18 3,4,5,6-Tetrabromo19 3,5-Difluoro20 3,5-Dibromo21 3-Methyl22 4-Methyl23 3-Ethyl24 4-Ethyl25 3-iso-Propyl26 4-iso-Propyl27 3-tert-Butyl28 4-tert-Butyl29 3,4-Dimethyl30 3,5-Dimethyl31 3,6-Dimethyl32 4,5-Dimethyl33 3,4,5-Trimthyl34 3,4,6-Trimethyl35 3,4,5,6-Tetramethyl36 3-Nitro37 4-Nitro38 3,5-Dinitro39 3-Cyano40 4-Cyano41 3-Methoxy42 4-Methoxy43 3-tert.Butoxy44 4-tert.Butoxy45 3-Trifluoromethyl46 4-Trifluoromethyl47 3-Chloromethyl48 4-Chloromethyl49 3-Trifluoromethoxy50 4-Trifluoromethoxy51 3-Benzyloxy52 4-Benzyloxy53 4,5-Dibenzyloxy54 3-Phenoxy55 4-Phenoxy56 3-Phenyl57 4-Phenyl58 3-Pyrid-2'-yl59 4-Pyrid-2'-yl60 3-Pyrid-2'-yloxy61 4-Pyrid-2'-yloxy______________________________________
TABLE VIII______________________________________ ##STR33##No. R.sup.8 n Data______________________________________1 H m.p. 152-155.degree. C.2 3-Fluoro3 4-Fluoro4 3-Chloro5 4-Chloro6 3-Bromo7 4-Bromo8 3-Iodo9 4-Iodo10 3,4-Dichloro11 3,5-Dichloro12 3,6-Dichloro13 4,5-Dichloro14 3,4,5-Trichloro15 3,4,6-Trichloro16 3,4,5,6-Tetrachloro17 3,4,5,6-Tetrafluoro18 3,4,5,6-Tetrabromo19 3,5-Difluoro20 3,5-Dibromo21 3-Methyl22 4-Methyl23 3-Ethyl24 4-Ethyl25 3-iso-Propyl26 4-iso-Propyl27 3-tert-Butyl28 4-tert-Butyl29 3,4-Dimethyl30 3,5-Dimethyl31 3,6-Dimethyl32 4,5-Dimethyl33 3,4,5-Trimethyl34 3,4,6-Trimethyl35 3,4,5,6-Tetramethyl36 3-Nitro37 4-Nitro38 3,5-Dinitro39 3-Cyano40 4-Cyano41 3-Methoxy42 4-Methoxy43 3-tert.Butoxy44 4-tert.Butoxy45 3-Trifluoromethyl46 4-Trifluoromethyl47 3-Chloromethyl48 4-Chloromethyl49 3-Trifluoromethoxy50 4-Trifluoromethoxy51 3-Benzyloxy52 4-Benzyloxy53 4,5-Dibenzyloxy54 3-Phenoxy55 4-Phenoxy56 3-Phenyl57 4-Phenyl58 3-Pyrid-2'-yl59 4-Pyrid-2'-yl60 3-Pyrid-2'-yloxy61 4-Pyrid-2'-yloxy______________________________________
TABLE IX______________________________________ ##STR34##No. X Y R.sup.1 R.sup.8 Data______________________________________1 CHSCH.sub.3 O CH.sub.3 H2 CHSCH.sub.3 NH CH.sub.3 H3 CHSCH.sub.3 S CH.sub.3 H4 CH.sub.2 O CH.sub.3 N5 CH.sub.2 NH CH.sub.3 H6 CH.sub.2 S CH.sub.3 H7 CHCH.sub.3 O CH.sub.3 H8 CHCH.sub.3 NH CH.sub.3 H9 CHCH.sub.3 S CH.sub.3 H10 CHCH.sub.3 O CH.sub.3 Perchloro11 CHCH.sub.3 NH CH.sub.3 Perchloro12 CHCH.sub.3 S CH.sub.3 Perchloro13 CHOCH.sub.3 NH CH.sub.3 H14 CHOCH.sub.3 S CH.sub.3 H15 CHOCH.sub.3 NH CH.sub.3 Perchloro16 CHOCH.sub.3 S CH.sub.3 Perchloro17 NOCH.sub.3 NH CH.sub.3 H18 NOCH.sub.3 S CH.sub.3 H19 NOCH.sub.3 NH CH.sub.3 Perchloro20 NOCH.sub.3 S CH.sub.3 Perchloro______________________________________
In general terms, 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 systemic action and can be used as foliar and soil fungicides.
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 novel compounds are particularly useful for controlling the following plant diseases:
Erysiphe graminis in cereals,
Erysiphe cichoracearum and Sphaerotheca fuliginea in curcurbits,
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 compounds are applied by spraying or dusting the plants with the active ingredients, or treating the seeds of the plants with the active ingredients. They may be applied before or after infection of the plants or seeds by the fungi. Either the fungi themselves, or the plants, seed or materials to be protected against fungus attack, or the soil are treated with a fungicidally effective amount of the active ingredient.
The novel substances can be converted into conventional formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend entirely on the purposes for which they are intended; they should at all events ensure a fine and uniform distribution of the active ingredient. 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 ligninsulfite waste liquors and methylcellulose.
The fungicides generally contain from 0.1 to 95, and preferably from 0.5 to 90, wt % of active ingredient. The application rates are from 0.02 to 3 kg or more of active ingredient per hectare, depending on the type of effect desired. The novel compounds may also be used for protecting materials, e.g., on Paecilomyces variotii. When the active ingredients are used for treating seed, amounts of from 0.001 to 50, and preferably from 0.01 to 10, g per kg of seed are generally required.
The agents and the ready-to-use formulations prepared from them, such as solutions, emulsions, suspensions, powders, dusts, pastes and granules, are applied in conventional manner, for example by spraying, atomizing, dusting, scattering, dressing or watering.
Examples of formulations are given below.
I. A solution of 90 parts by weight of compound no. 429 (Table I) 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. 14 (Table II), 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. 49 (Table I), 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. By finally dispersing the solution in water, an aqueous dispersion is obtained.
IV. An aqueous dispersion of 20 parts by weight of compound no. 56 (Table I), 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. By finely distributing the solution in water, an aqueous dispersion is obtained.
V. A hammer-milled mixture of 80 parts by weight of compound no. 14 (Table I), 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 powered silica gel. By finely dispersing the mixture in water, a spray liquor is obtained.
VI. An intimate mixture of 3 parts by weight of compound no. 17 (Table II) and 97 parts by weight of particulate kaolin. The dust contains 3 wt % of the active ingredient.
VII. An intimate mixture of 30 parts by weight of compound no. 17 (Table I), 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. 571 (Table I), 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts by weight of water, which dispersion can be further diluted.
IX. A stable oily dispersion of 20 parts by weight of compound no. 616 (Table I), 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-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil.
In these application forms, the agents according to the invention may also be present together with other active ingredients, for example herbicides, insecticides, growth regulators, and fungicides, and may furthermore be mixed and applied together with fertilizers. Admixture with other fungicides frequently results in a greater fungicidal action spectrum.
USE EXAMPLES
The active ingredient used for comparison purposes was 2-(phenoxymethyl) phenylglyoxylic acid-methyl ester-O-methyloxime (A) disclosed in EP 253,213.
Use Example 1
Action on wheat brown rust
Leaves of pot-grown wheat seedlings of the "Kanzler" variety were dusted with spores of brown rust (Puccinia recondita). The pots were then placed for 24 hours at 20.degree. to 22.degree. C. in a high-humidity (90-95%) chamber. During this period the spores germinated and the germ tubes penetrated the leaf tissue. The infected plants were then sprayed to runoff with aqueous liquors containing (dry basis) 80% of active ingredient and 20% of emulsifier. After the sprayed-on layer had dried, the plants were set up in the greenhouse at 20.degree. to 22.degree. C. and a relative humidity of 65 to 70%. The extent of rust fungus spread on the leaves was assessed after 8 days.
The results show that active ingredients nos. 49, 429, 56, 14, 15, 16, 17, 582, 578, 573, 592, 571, 704, 705 and 616 from Table I and nos. 17 and 644 from Table II, applied as 0.025 wt% spray liquors, have a better fungicidal action (95%) than prior art comparative compound A (50%).
Use Example 2
Action on Pyricularia oryzae (protective)
Leaves of pot-grown rice seedlings of the "Bahia" variety were sprayed to runoff with aqueous emulsions containing (dry basis) 80% of active ingredient and 20% of emulsifier, and inoculated 24 hours later with an aqueous spore suspension of Pyricularia oryzae. The plants were then set up in climatic cabinets at 22.degree. to 24.degree. C. and 95 to 99% relative humidity. The extent of fungus attack was assessed after 6 days.
The results show that active ingredients nos. 429, 583, 593, 592, 571, 706 and 616 from Table I and nos. 14, 15, 16, 17, 582, 592, 571, 769, 782, 672, 644 and 583 from Table II, applied as 0.05 wt % spray liquors, have a very good fungicidal action (100%).
The novel compounds are also suitable for effectively combating pests such as insects, arachnids and nematodes. They may be used as pesticides in crop protection and in the hygiene, stores protection and veterinary sector.
Examples of injurious insects belonging to the Lepidoptera order are Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholita funebrana, Grapholita molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keifferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flamea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Platypena scarbra, Plutella xylostella, Pseudoplusia includens, Phyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerelella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis.
Examples from the Coleoptera order are Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Onlema oryzae, Ortiorrhynchus sulcatus, Ortiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotretra nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria.
Examples from the Diptera order are Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossia morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa. Examples from the Thysanoptera order are Franklinella fusca, Franklinielle occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci.
Examples from the Hymenoptera order are Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta.
Examples from the Heteroptera order are Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euchistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor.
Examples from the nematodes class are root-knot nematodes, e.g., Meloidogyne hapla, Meloidogyne incognita and Meloidogyne javanica, cyst-forming nematodes, e.g., Globodera rostochiensis, Heterodera avenae, Hetrodera glycinae, Heterodera schachtii and Heterodera trifolii, and stem and leaf eelworms, e.g., Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus and Pratylenchus goodeyi.
When the active ingredients are used for combating pests, the concentrations in the finished formulations may vary over a wide range. Generally, the concentration is from 0.0001 to 10, and preferably from 0.001 to 0.1, %.
The active ingredients may also be successfully used in the ultra-low-volume method (ULV), where it is possible to apply formulations containing more than 95 wt % of active ingredient, or even the active ingredient without any additives.
When the active ingredients are used for combating pests in the open, the application rates are from 0.01 to 10, and preferably from 0.1 to 1.0, kg/ha.
Use Example 3
Tetranychus telarius (spider mite); contact action--spray test
Potted bush beans which had developed the first pair of true leaves and were heavily infested with all stages of the spider mite Tetranychus telarius were sprayed to runoff in a spray cabinet with aqueous formulations of the active ingredients. The plants were placed on a rotating disc and sprayed from all sides with 50 ml of spray liquor. The plants were heavily infested with mites and numerous eggs had been laid on them. The action was assessed after 5 days by means of a binocular microscope. During this period, the plants were kept under normal greenhouse conditions.
______________________________________ Application rate Mortality in ppm In %______________________________________Compound no.from Table I49 100 8036 100 8043 1000 100429 1000 10038 40 10039 100 10045 1000 100582 about 20 100579 20 80583 40 100573 20 100593 1000 80592 40 100704 about 20 100705 40 100Compound no.from Table II37 1000 10039 1000 10045 1000 100______________________________________
Use Example 4
Musca domestica (housefly); continuous contact action
Both the tops and bottoms of Petri dishes 10 cm in diameter were lined with a total of 1 ml of acetonic solutions of the active ingredients. After the solvent had evaporated (about 30 mins.) , 10 flies and absorbent cotton steeped in water were introduced into each dish and the dishes closed. The flies in supine position were counted after 24 hours.
If a kill rate of 80 to 100% occurs at a concentration of 0.01 mg/dish, the test is continued with falling concentrations.
______________________________________Compound no. Application rate Mortalityfrom Table I in mg in %______________________________________49 0.1 8036 1.0 8037 0.1 100582 0.1 80593 0.1 60705 0.1 100706 0.1 100______________________________________
Use Example 5
Plutella maculipennis (diamondback moth); ingestion-inhibiting action
Young kohlrabi leaves are dipped for 3 seconds into aqueous solutions of the candidate compounds, and then placed on a round filter paper 9 cm in diameter which has been moistened with 0.5 ml of water. The filter paper is then placed in a Petri dish 10 cm in diameter. 10 caterpillars in the 4th larval stage are then placed on each leaf, and the Petri dish is closed. Ingestion inhibition is determined in % after 48 hours.
______________________________________Compound no. Application rate Mortalityfrom Table I in ppm in %______________________________________49 200 8036 200 80429 1000 8016 400 80582 400 100593 1000 80592 400 80705 400 80706 400 80______________________________________
Use Example 6
Action on Peronospora in grapes
Leaves of potted vines of the "M uller Thurgau" variety were sprayed with aqueous liquors containing (dry basis) 80% of active ingredient and 20% of emulsifier. To assess the duration of action of the active ingredients, the plants were, after the sprayed-on layer had dried, set up in the greenhouse for 8 days. Only then were the leaves infected with a zoospore suspension of Plasmopara viticola. The vines were then placed for 48 hours in a water-vapor-saturated chamber at 24.degree. C. and then for 5 days in a greenhouse at from 20.degree. to 30.degree. C. To accelerate the sporangiophore discharge, the plants were then again set up in the moist chamber for 16 hours. The extent to which the leaves had been attacked was then assessed.
The results show that active ingredients nos. 49, 429, 56, 14, 15, 16, 17, 582, 578, 573, 592, 571, 704, 705, 616, 117, 156, 579, 583, 593 and 706 from Table I, Nos. 17, 644, 117, 429, 56, 43, 36, 49, 14, 15, 16, 582, 614 and 672 from Table II, and compound no. 1 from Table VII have, when applied as 0.025 wt % spray liquors, a better fungicidal action (95%) than the prior art comparative agent A (50%).

Number	Date	Country	Kind
40 20 384.0	Jun 1990	DEX
40 20 388.3	Jun 1990	DEX

Number	Name	Date
5055471	DeFraine et al.	Oct 1991
5221691	Clough et al.	Jun 1993
5238956	Clough et al.	Aug 1993
5342837	Clough et al.	Aug 1994
5346902	Clough et al.	Sep 1994
5371084	DeFraine et al.	Dec 1994
5432197	DeFraine et al.	Jul 1995

Number	Date	Country
0414572	Feb 1991	EPX
414153	Feb 1991	EPX
426460	May 1991	EPX
460575	Dec 1991	EPX

	Number	Date
Parent	328516	Oct 1994
Parent	165413	Dec 1993
Parent	962340	Oct 1992
Parent	722209	Jun 1991

O-Benzyloxime ethers and crop protection agents containing these compounds

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