TREA

O-benzyloxime ethers and crop protection agents containing these compounds

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Information

  • Patent Grant
  • RE37839
  • Patent Number
    RE37,839
  • Date Filed
    Friday, April 5, 1996
    28 years ago
  • Date Issued
    Tuesday, September 10, 2002
    22 years ago
Information
Abstract
O-Benzyloxime ethers of the formula I wherein5 x is substituted or unsubstituted CH2, NOalkylY is O, S, NR5 R1, R2, R5 are H, alkylZ1, Z2 are H, halogen, methyl, methoxy, cyanoR3, R4 are hydrogen, cyano, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, benzylthio, alkylcarbonyl, substituted or unsubstituted benzylcarbonyl, alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl substituted or unsubstituted benzyloxycarbonyl,N(R6)2, where R6 is H, alkyl, substituted or unsubstituted phenyl,—CO—N(R7)2, where R7 is H, substituted or unsubstituted alkyl,substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted hetaryl, substituted or unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclyloxy,R3 and R4 together may form a carbocyclic or heterocyclic ring which is substituted or unsubstituted, andR3 or R4 may be halogen, or may be wheren is an integer from 1 to 4, andR8 is, or, when n>1, the R8's are identical or different and are each, H, halogen, cyano, nitro or substituted or unsubstituted C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, aryl, aryloxy, benzyloxy, hetaryl or hetaryloxy,and crop protection agents containing these compounds.
Description




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











where




X is CH


2


, CH—C


1


-C


4


-alkyl, CH—C


1


-C


4


-alkoxy, CH—C


1


-C


4


-alkylthio or N—C


1


-C


4


-alkoxy,




Y is O, S or NR


5


,




R


1


, R


2


and R


5


are each H or C


1


-C


4


-alkyl,




Z


1


and Z


2


are identical or different and are each H, halogen, methyl, methoxy or cyano,




R


3


and R


4


are identical or different and are each hydrogen, cyano, straight-chain or branched C


1


-C


10


-alkyl, C


1


-C


4


-haloalkyl, C


3


-C


6


-cycloalkyl, C


3


-C


6


-halocycloalkyl, C


3


-C


6


-cycloalkyl-C


1


-C


4


-alkyl, C


1


-C


4


-alkoxy-C


1


-C


4


-alkyl, C


1


-C


4


alkylthio-C


1


-C


4


-alkyl, arylthio-C


1


-C


4


-alkyl, C


2


-C


6


-alkenyl, C


2


-C


5


-haloalkenyl, C


3


-C


6


-cycloalkenyl, C


3


-C


6


-halocycloalkenyl, C


2


-C


6


-alkynyl, C


1


-C


6


-alkoxy, C


1


-C


4


-haloalkoxy, C


1


-C


4


-alkylthio, benzylthio, C


1


-C


4


-alkylcarbonyl, unsubstituted or substituted phenylcarbonyl, unsubstituted or substituted benzylcarbonyl, C


1


-C


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


1


-C


4


-alkyl, unsubstituted or substituted aryl-C


1


-C


4


-alkenyl, unsubstituted or substituted aryloxy-C


1


-C


6


-alkyl, unsubstituted or substituted arylthio-C


1


-C


4


-alkyl, unsubstituted or substituted hetaryl, unsubstituted or substituted hetaryloxy, unsubstituted or substituted betarylthio, unsubstituted or substituted hetaryl-C


1


-C


4


-alkyl, unsubstituted or substituted hetaryl-C


2


-C


4


-alkenyl, unsubstituted or substituted heteryloxy-C


1


-C


4


-alkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocyclyloxy, N(R


6


)


2


, where the radicals R


6


are identical or different and are each H, C


1


-C


4


-alkyl or unsubstituted or substituted phenyl, or




—CO—N(R


7


)


2


, where the radicals R


7


are identical or different and are each H or C


1


-C


4


-alkyl, substitutents, in addition to hydrogen, being halogen, cyano, nitro, C


1


-C


4


-alkyl, C


1


-C


4


-alkoxy, C


1


-C


4


-haloalkyl, C


1


-C


4


-haloalkoxy, C


1


-C


10


-alkoximino-C


1


- or C


2


-alkyl, aryl, aryloxy, benzyloxy, hetaryl, hetaryloxy, C


3


-C


6


-cycloalkyl, heterocyclyl or heterocyclyloxy, or




R


3


and R


4


together may form a carbocyclic or heterocyclic ring which may be substituted by the above-mentioned substituents, and




R


3


or R


4


may be halogen, or











may be











where




n is an integer from 1 to 4, and




R


8


is, or, when n>1, the R


8


's are identical or different and are each, H, halogen, cyano, nitro or substituted or unsubstituted C


1


-C


4


-alkyl, C


1


-C


4


-alkoxy, C


1


-C


4


haloalkyl, C


1


-C


4


-haloalkoxy, aryl, aryloxy, benzyloxy, hetaryl or hetaryloxy,




have excellent fungicidal, insecticidal, nematicidal and scaricidal 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


1


-C


4


-alkylidene (eg. methylidene, ethylidene, nor isopropylidene, n-, iso-, sec- or tert-butylidene),




C


1


-C


4


-alkoxymethylidene (eg. methoxy-ethoxy-, n-propoxy, isopropoxy-, n-butoxy-, isobutoxy-, sec-butoxy- or tertbutoxymethylidene), C


1


-C


4


-alkylthiomethylidene (eg. methyl-, ethyl-, n-propyl-, isopropyl-, n-butylthio-, isobutylthio-, sec-butylthio- or tert-butylthiomethylidene) or C


1


-C


4


-alkoximino (eg. methoximino, ethoximino, n-propoximino, isopropoximino, n-butoximino, isobutoximino, sec-butoximino or tert-butoximino),




Y may be O, S or NR


5


,




R


1


, R


2


and R


5


may each be H or C


1


-C


4


-alkyl (eg. methyl, ethyl, n- or isopropyl, n- or iso-, sec- or tert-butyl),




Z


1


and Z


2


may be H, halogen (eg. fluorine, chlorine, bromine or iodine), methyl, methoxy or cyano, and




R


3


and R


4


may be identical or different and are each hydrogen, cyano, straight-chain or branched C


1


-C


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


1


-C


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


3


-C


6


-cycloalkyl (eg. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl), C


3


-C


6


-halocycloalkyl (eg. 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-dichloro-3-methylcyclopropyl or tetrafluorocyclobutyl), C


3


-C


8


-cycloalkyl-C


1


-C


4


-alkyl (eg. 1-methylcyclopropyl, 2,2-dimethylcyclopropyl or 1-methylcyclohexyl), C


1


-C


4


-alkoxy-C


1


-C


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


1


-C


4


-alkylthio-C


1


-C


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


1


-C


4


-alkyl (eg. phenylthiomethyl or 2-chlorophenylthiomethyl), C


2


-C


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


2


-C


5


-haloalkenyl (eg. 2,2-difluorovinyl, 2,2-dichlorovinyl, 3,3,3-trifluoropropenyl, 3,3,3-trichloropropenyl or 3-chloro-2-propenyl), C


3


-C


6


-cycloalkenyl (eg. cyclopent-1-enyl, cyclopentadienyl or cyclohex-1-enyl), C


3


-C


6


-halocycloalkenyl (eg. pentafluorocyclopentadienyl or pentachlorocyclopentadienyl), C


2


-C


4


-alkynyl (eg. ethnyl, 1-propynyl or 1-propargyl), C


1


-C


4


-alkoxy (eg. methoxy, ethoxy, n- or isopropoxy or n-, iso-, sec- or tert-butoxy), C


1


-C


4


-alkylthio (eg. methylthio, ethylthio, n- or isopropylthio or n-, iso-, sec- or tert-butylthio) or banzylthio, C


1


-C


4


-haloalkoxy (eg. trifluoromethoxy, pentafluoroethoxy or 1,1,2,2-tetrafluoroethoxy), N(R


6


)


2


(eg. amino, methylamino, dimethylamino, ethylamino, diethylamino, di-n-propylamino, diisopropylamino, di-n-butylamino or diisobutylamino), C


1


-C


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


1


-C


4


-alkoxycarbonyl (eg. methoxycarbonyl, ethoxycarbonyl, n- or isopropoxycarbonyl or n-, iso-, sec- or tertbutoxycarbonyl), unsubstituted or substituted phenoxycarbonyl (eg. phenoxycarbonyl or 4-chlorophenoxycarbonyl), unsubstituted or substituted benzyloxycarbonyl (eg. benzyloxycarbonyl), —CO—N(R


7


)


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


1


-C


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


1


-C


4


-alkenyl (eg. phenyl-1-etheny 1,2-phenyl-1-propenyl, 2,2-diphexylethenyl, 1-phenyl-1-propen-2-yl or 1-phenyl-1-ethenyl), unsubstituted or substituted aryloxy-C


1


-C


4


-alkyl (eg. phenoxymethyl), unsubstituted or substituted arylthio-C


1


-C


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


1


-C


4


-alkyl (eg. 2-pyridylmethyl or 3-pyridylmethyl), unsubstituted or substituted hetaryloxy-C


1


-C


4


-alkyl (eg. furfurylmethoxy, thienylmethoxy, 3-isoxazolylmethoxy, 2-oxazolylmethoxy or 2-pyridylmethoxy), unsubstituted or substituted hetaryl-C


2


-C


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-2yl, 1,3-dioxolan-2-yl and tetrahydropyran-2-yloxy.




The group











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, violaric acid or N,N-dimethylvioluric acid).




R


3


and R


4


together then form, for example, a cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralin, indane or fluorene ring.




One of the radicals R


3


or R


4


may furthermore be halogen (eg. fluorine, chlorine, bromine or iodine).




n may be 1, 2, 3 or 4 and R


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


3


and R


4


are hydrogen, the preferred compounds are those in which either only R


3


or only R


4


is hydrogen, in particular the compounds in which R


3


is hydrogen.




Also preferred are compounds of the formula II in which X is CH


2


, CHCH


3


, CHC


2


H


5


, CHOCH


3


, CHOC


2


H


5


, CHSCH


3


or CHSC


2


H


5


, Y is 0, R


1


is C


1


-C


4


-alkyl, R


2


is H or methyl, R


3


and R


4


are identical or different and each is hydrogen, cyano, straight-chain or branched C


1


-C


10


-alkyl, C


1


-C


4


-haloalkyl, C


3


-C


6


-cycloalkyl, C


3


-C


6


-halocycloalkyl, C


3


-C


6


-cycloalkyl-C


1


-C


4


-alkyl, C


1


-C


4


-alkoxy-C


1


-C


4


-alkyl, C


1


-C


4


-alkylthio-C


1


-C


4


-alkyl, arylthio-C


1


-C


4


-alkyl, C


2


-C


6


-alkenyl, C


2


-C


6


-alkynyl, C


2


-C


4


-haloalkenyl, C


1


-C


6


-alkoxy, C


1


-C


6


-alkylthio, C


1


-C


4


-alkylcarbonyl, C


1


-C


4


-alkoxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C


1


-C


4


-alkyl, substituted or unsubstituted aryl-C


2


-C


4


-alkenyl, substituted or unsubstituted aryloxy-C


1


-C


4


-alkyl, substituted or unsubstituted hetaryl, substituted or unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio or substituted or unsubstituted heterocyclyl, or each is N(R


6


)


2


, R


6


being identical or different and denoting H, C


1


-C


6


-alkyl, C


3


-C


6


-cycloalkyl or substituted or unsubstituted phenyl, or each is —CO—N(R


7


)


2


, R


7


being identical or different and denoting H or C


1


-C


4


-alkyl, the term “substituted” denoting the radicals listed in claim


1


, and R


3


and R


4


may together denote a carbocyclic or heterocyclic ring which may be substituted by the radicals given under “substituted”, and R


3


and R


4


may be halogen, and Z


1


and Z


2


are hydrogen, fluorine, chlorine, bromine, iodine, methyl, cyano or methoxy.




Owing to the C═C or C═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 a pesticides.




The compounds of the general formula I as claimed in claim


1


are prepared, for example, as described in Scheme 1 (Z


1


and Z


2


are each H).











The compounds of the general formula I in which X is CH


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


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


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 244077 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


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 tert-butylate, 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 nitrate, 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


1


is usually alkoxy.




The compounds in which YR


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


1


is COOAlkyl (10) (cf. Scheme 2):











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


1


and R


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


2


═H) is known.




(YR


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.











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


4


═CN) (cf. M. R. Zimmermann J. f. prakt. Chemie 66 (1902), 359).




The specific derivatives in which R


3


is CN and R


4


is alkoxyalkyl are prepared according to European Patent 74,047, those in which R


3


is CN and R


4


is alkylthioalkyl according to European Patent 150,822 and those in which R


3


is CN and R


4


is alkyl according to DE 2 304 848.




The method employing Me


3


SiO—NH—SiMe


3


(R. U. Hoffmann and G. A. Buntain, Synthesis 1987, 831) is used for sterically hindered ketones.











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


1


-R


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 or 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


1


═OAlkyl, X═CH—OAlkyl or N—OAlkyl and L═Cl, Br, tosylate or mesylate) is illustrated by Scheme 5:











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 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: 3,4-Dichloroacetophenone 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


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 3×100 ml of tert-butyl methyl ether. The organic phase is washed with water, dried with Na


2


SO


4


and evaporated down. 19.6 g (96% of theory) of crystals of melting point 92° C., which according to


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° to −60° C. 153.5 g (2.15 mol) of chlorine are then passed in and the temperature is increased to −20° C.; stirring is carried out for 1 hour, the mixture is then evaporated down in a rotary evaporator at 10° 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°-15° C. (exothermic). Stirring is carried out for 5 hours at room temperature (20° 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° C.




After filtration under suction and drying, 208 g (66% of theory) of a spectroscopically pure substance of melting point 105°-106° 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° to −10° 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° 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


2


O are initially taken at 10° 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


2


SO


4


, evaporating down and crystallizing from dichloromethane/n-hexane give 41.1 g (63% of theory) of a white powder of melting point 102°-104° 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° 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°-158° C. remain.






1


H-NMR (CDCl


3


) δ=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


1


H-NMR about 90%).






1


H-NMR (CDCl


3


) δ=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° 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°-155° C. remain.






1


H-NMR (CDCl


3


) δ=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.






1


H-NMR (CDCl


3


): δ=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 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°-88° C. are obtained.






1


H-NMR (CDCl


3


): δ=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)-imminooxymethyl]-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 3×50 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


−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°-97° C. result.






1


H-NMR (CDCl


3


): δ=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 NaH—CO


3


and evaporated down, and the residue is chromatographed over SiO


2


using methyl tert-butyl ether/hexane. 2.1 g (51% of theory) of crystals of melting point 105°-107° C. result.






1


H-NMR (CDCl


3


): δ=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°-89° C. are obtained.






1


H-NMR (CDCl


3


): δ=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° 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°-89° C. were obtained.






1


H-NMR (CDCl


3


): δ=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°-84° 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° 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°-155° C.






1


H-NMR (CDCl


3


): δ=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








































No.




R


3






R


4






Data









 1




Cl




Phenyl







 2




Cl




Cyano






 3




Cl




Ethoxycarbonyl






 4




Cl




Cyclopropyl






 5




CF


3






CF


3








 6




CF


3






Phenyl






 7




CCl


3






CCl


3








 8




CCl


3






Phenyl






 9




CH


2


Cl




Phenyl






 10




CH


2


CF


3






Phenyl






 11




CF


2


Cl




Phenyl






 12




CHCl


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, 1086, 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, 1006






 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




Methoxycarbonyl






100




CN




Ethoxycarbonyl






101




CN




n-Propoxycarbonyl






102




CN




iso-Propoxycarbonyl






103




CN




n-Butoxycarbonyl






104




CN




iso-Butoxycarbonyl






105




CN




sec.-Butoxycarbonyl






106




CN




tert.-Butoxycarbonyl






107




CN




n-Hexoxycarbonyl






108




CN




Phenoxycarbonyl






109




CN




4-Chlorophenoxycarbonyl






110




CN




Benzyloxycarbonyl






111




CN




Aminocarbonyl






112




CN




Dimethylaminocarbonyl






113




CN




Diethylaminocarbonyl






114




CN




Di-iso-Propylaminocarbonyl






115




CN




Phenylaminocarbonyl






116




CN




N-Methyl-N-Phenylaminocarbonyl






117




CN




Phenyl




oil; IR (film): 1245, 1127, 1024, 1015, 767, 750






118




CN




2-Fluorophenyl






119




CN




3-Fluorophenyl






120




CN




4-Fluorophenyl






121




CN




Pentafluorophenyl






122




CN




2-Chlorophenyl






123




CN




3-Chlorophenyl






124




CN




4-Chlorophenyl






125




CN




Pentachlorophenyl






126




CN




2,3-Dichlorophenyl






127




CN




2,4-Dichlorophenyl






128




CN




2,5-Dichlorophenyl






129




CN




2,6-Dichlorophenyl






130




CN




3,4-Dichlorophenyl






131




CN




3,5-Dichlorophenyl






132




CN




2,3,4-Trichlorophenyl






133




CN




2,3,5-Trichlorophenyl






134




CN




2,3,6-Trichlorophenyl






135




CN




2,4,5-Trichlorophenyl






136




CN




2,4,6-Trichlorophenyl






137




CN




3,4,5-Trichlorophenyl






138




CN




2,3,4,6-Tetrachlorophenyl






139




CN




2,3,5,6-Tetrachlorophenyl






140




CN




2-Bromophenyl






141




CN




3-Bromophenyl






142




CN




4-Bromophenyl






143




CN




2,4-Dibromophenyl






144




CN




3-Bromo-4-fluorophenyl






145




CN




3-Bromo-4-methoxyphenyl






146




CN




2-Iodophenyl






147




CN




3-Iodophenyl






148




CN




4-Iodophenyl






149




CN




2-Chloro-4-fluorophenyl






150




CN




2-Chloro-5-fluorophenyl






151




CN




2-Chloro-6-fluorophenyl






152




CN




2-Chloro-4-bromophenyl






153




CN




2-Bromo-4-chlorophenyl






154




CN




2-Bromo-4-fluorophenyl






155




CN




3-Bromo-4-chlorophenyl






156




CN




3-Chloro-4-fluorophenyl






157




CN




3-Fluoro-4-chlorophenyl






158




CN




2-Cyanophenyl






159




CN




3-Cyanophenyl






160




CN




4-Cyanophenyl






161




CN




2-Nitrophenyl






162




CN




3-Nitrophenyl






163




CN




4-Nitrophenyl






164




CN




2-Methylphenyl






165




CN




3-Methylphenyl






166




CN




4-Methylphenyl






167




CN




2,4-Dimethylphenyl






168




CN




2,6-Dimethylphenyl






169




CN




3,4-Dimethylphenyl






170




CN




3,5-Dimethylphenyl






171




CN




2,3,4-Trimethylphenyl






172




CN




2,3,5-Trimethylphenyl






173




CN




2,3,6-Trimethylphenyl






174




CN




2,4,5-Trimethylphenyl






175




CN




2,4,6-Trimethylphenyl






176




CN




3,4,5-Trimethylphenyl






177




CN




Pentamethylphenyl






178




CN




2-Ethylphenyl






179




CN




3-Ethylphenyl






180




CN




4-Ethylphenyl






181




CN




3,5-Diethylphenyl






182




CN




2-n-Propylphenyl






183




CN




3-n-Propylphenyl






184




CN




4-n-Propylphenyl






185




CN




2-iso-Propylphenyl






186




CN




3-iso-Propylphenyl






187




CN




4-iso-Propylphenyl






188




CN




2,4-Di-iso-Propylphenyl






189




CN




3,5-Di-iso-Propylphenyl






190




CN




4-n-Butylphenyl






191




CN




4-sec.-Butylphenyl






192




CN




4-iso-Butylphenyl






193




CN




4-tert.-Butylphenyl






194




CN




3-tert.-Butylphenyl






195




CN




2-tert.-Butylphenyl






196




CN




2,4-Di-tert.-Butylphenyl






197




CN




3,5-Di-tert.-Butylphenyl






198




CN




4-n-Hexylphenyl






199




CN




4-n-Dodecylphenyl






200




CN




2-Methyl-4-tert.-Butylphenyl






201




CN




2-Methyl-6-tert.-Butylphenyl






202




CN




2-Methyl-4-iso-Propylphenyl






203




CN




2-Methyl-4-Cyclophexylphenyl






204




CN




2-Methyl-4-Phenylphenyl






205




CN




2-Methyl-4-Benzylphenyl






206




CN




2-Methyl-4-Phenoxyphenyl






207




CN




2-Methyl-4-Benzyloxyphenyl






208




CN




2-Methyl-3-Chlorophenyl






209




CN




2-Methyl-4-Chlorophenyl






210




CN




2-Methyl-5-Chlorophenyl






211




CN




2-Methyl-6-Chlorophenyl






212




CN




2-Methyl-4-Fluorophenyl






213




CN




2-Methyl-3-Bromophenyl






214




CN




2-Methyl-4-Bromophenyl






215




CN




2-Methyl-3-Methoxyphenyl






216




CN




2-Methyl-4-Methoxyphenyl






217




CN




2-Methyl-5-methoxyphenyl






218




CN




2-Methyl-6-methoxyphenyl






219




CN




2-Methyl-4-iso-Propoxyphenyl






220




CN




2-Methyl-2,5-dimethoxyphenyl






221




CN




2-Methoxyphenyl






222




CN




3-Methoxyphenyl






223




CN




4-Methoxyphenyl






224




CN




2,3-Dimethoxyphenyl






225




CN




2,4-Dimethoxyphenyl






226




CN




2,5-Dimethoxyphenyl






227




CN




2,6-Dimethoxyphenyl






228




CN




3,4-Dimethoxyphenyl






229




CN




3,5-Dimethoxyphenyl






230




CN




3,6-Dimethoxyphenyl






231




CN




2,3,4-Trimethoxyphenyl






232




CN




2,3,5-Trimethoxyphenyl






233




CN




2,3,6-Trimethoxyphenyl






234




CN




2,4,5-Trimethoxyphenyl






235




CN




2,4,6-Trimethoxyphenyl






236




CN




3,4,5-Trimethoxyphenyl






237




CN




2-Ethoxyphenyl






238




CN




3-Ethoxyphenyl






239




CN




4-Ethoxyphenyl






240




CN




2-iso-Propoxyphenyl






241




CN




3-iso-Propoxyphenyl






242




CN




4-iso-Propoxyphenyl






243




CN




3-tert.-Butoxyphenyl






244




CN




4-tert.-Butoxyphenyl






245




CN




2-Trifluoromethoxyphenyl






246




CN




3-Trifluoromethoxyphenyl






247




CN




4-Trifluoromethoxyphenyl






248




CN




3-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl






249




CN




4-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl






250




CN




2-Chloromethylphenyl






251




CN




3-Chloromethylphenyl






252




CN




4-Chloromethylphenyl






253




CN




2-Trifluoromethylphenyl






254




CN




3-Trifluoromethylphenyl






255




CN




4-Trifluoromethylphenyl






256




CN




2-(Methoxyiminomethyl)phenyl






257




CN




3-(Methoxyiminomethyl)phenyl






258




CN




4-(Methoxyiminomethyl)phenyl






259




CN




2-(Ethoxyiminomethyl)phenyl






260




CN




3-(Ethoxyiminomethyl)phenyl






261




CN




4-(Ethoxyiminomethyl)phenyl






262




CN




2-(n-Propoxyiminomethyl)phenyl






263




CN




3-(n-Propoxyiminomethyl)phenyl






264




CN




4-(n-Propoxyiminomethyl)phenyl






265




CN




2-(iso-Propoxyiminomethyl)phenyl






266




CN




3-(iso-Propoxyiminomethyl)phenyl






267




CN




4-(iso-Propoxyiminomethyl)phenyl






268




CN




2-(n-Butoxyiminomethyl)phenyl






269




CN




3-(n-Butoxyiminomethyl)phenyl






270




CN




4-(n-Butoxyiminomethyl)phenyl






271




CN




2-(iso-Butoxyiminomethyl)phenyl






272




CN




3-(iso-Butoxyiminomethyl)phenyl






273




CN




4-(iso-Butoxyiminomethyl)phenyl






274




CN




2-(tert.-Butoxyiminomethyl)phenyl






275




CN




3-(tert.-Butoxyiminomethyl)phenyl






276




CN




4-(tert.-Butoxyiminomethyl)phenyl






277




CN




2-(n-Pentoxyiminomethyl)phenyl






278




CN




3-(n-Pentoxyiminomethyl)phenyl






279




CN




4-(n-Pentoxyiminomethyl)phenyl






280




CN




2-(n-Hexoxyiminomethyl)phenyl






281




CN




3-(n-Hexoxyiminomethyl)phenyl






282




CN




4-(n-Hexoxyiminomethyl)phenyl






283




CN




2-(Allyloxyiminomethyl)phenyl






284




CN




3-(Allyloxyiminomethyl)phenyl






285




CN




4-(Allyloxyiminomethyl)phenyl






286




CN




2-(Benzyloxyiminomethyl)phenyl






287




CN




3-(Benzyloxyiminomethyl)phenyl






288




CN




4-(Benzyloxyiminomethyl)phenyl






289




CN




2-(Methoxyimino-1′-ethyl)phenyl






290




CN




3-(Methoxyimino-1′-ethyl)phenyl






291




CN




4-(Methoxyimino-1′-ethyl)phenyl






292




CN




2-(Ethoxyimino-1′-ethyl)phenyl






293




CN




3-(Ethoxyimino-1′-ethyl)phenyl






294




CN




4-(Ethoxyimino-1′-ethyl)phenyl






295




CN




2-(n-Propoxyimino-1′-ethyl)phenyl






296




CN




3-(n-Propoxyimino-1′-ethyl)phenyl






297




CN




4-(n-Propoxyimino-1′-ethyl)phenyl






298




CN




2-(n-Butoxyimino-1′-ethyl)phenyl






299




CN




3-(n-Butoxyimino-1′-ethyl)phenyl






300




CN




4-(n-Butoxyimino-1′-ethyl)phenyl






301




CN




2-(n-Pentoxyimino-1′-ethyl)phenyl






302




CN




3-(n-Pentoxyimino-1′-ethyl)phenyl






303




CN




4-(n-Pentoxyimino-1′-ethyl)phenyl






304




CN




2-(n-Hexoxyimino-1′-ethyl)phenyl






305




CN




3-(n-Hexoxyimino-1′-ethyl)phenyl






306




CN




4-(n-Hexoxyimino-1′-ethyl)phenyl






307




CN




2-(Allyloxyimino-1′-ethyl)phenyl






308




CN




3-(Allyloxyimino-1′-ethyl)phenyl






309




CN




4-(Allyloxyimino-1′-ethyl)phenyl






310




CN




2-(Benzyloxyimino-1′-ethyl)phenyl






311




CN




3-(Benzyloxyimino-1′-ethyl)phenyl






312




CN




4-(Benzyloxyimino-1′-ethyl)phenyl






313




CN




2-Phenylphenyl






314




CN




3-Phenylphenyl






315




CN




4-Phenylphenyl






316




CN




2-Phenoxyphenyl






317




CN




3-Phenoxyphenyl






318




CN




4-Phenoxyphenyl






319




CN




2-Benzyloxyphenyl






320




CN




3-Benzyloxyphenyl






321




CN




4-Benzyloxyphenyl






322




CN




4-(Imidazol-1′-yl)phenyl






323




CN




4-(Piperazin-1′-yl)phenyl






324




CN




4-(Morpholin-1′-yl)phenyl






325




CN




4-(Piperidin-1′-yl)phenyl






326




CN




4-(Pyridyl-2′-oxy)phenyl






327




CN




2-Cyclopropylphenyl






328




CN




3-Cyclopropylphenyl






329




CN




4-Cyclopropylphenyl






330




CN




3-Cyclohexylphenyl






331




CN




4-Cyclohexylphenyl






332




CN




4-Oxiranylphenyl






333




CN




4-(1′,3′-Diozan-2′-yl)phenyl






334




CN




4-(Tetrahydropyran-2-yloxy)phenyl






335




CN




1-Naphthyl






336




CN




2-Naphthyl






337




CN




9-Anthryl






338




CN




1-Naphtoxy






339




CN




2-Naphtoxy






340




CN




9-Anthroxy






341




CN




Phenoxy






342




CN




2-Chlorophenoxy






343




CN




3-Chlorophenoxy






344




CN




4-Chlorophenoxy






345




CN




4-Methylphenoxy






346




CN




4-tert.-Butylphenoxy






347




CN




4-Methoxyphenoxy






348




CN




4-Ethoxyphenoxy






349




CN




4-tert.-Butoxyphenoxy






350




CN




Phenylthio






351




CN




2-Chlorophenylthio






352




CN




4-Chlorophenylthio






353




CN




Benzyl






354




CN




2-Methylbenzyl






355




CN




3-Methylbenzyl






356




CN




4-Methylbenzyl






357




CN




4-tert.-Butylbenzyl






358




CN




2-Chlorobenzyl






359




CN




3-Chlorobenzyl






360




CN




4-Chlorobenzyl






361




CN




2,4-Dichlorobenzyl






362




CN




2,6-Dichlorobenzyl






363




CN




2,4,6-Trichlorobenzyl






364




CN




2-Trifluoromethylbenzyl






365




CN




3-Trifluoromethylbenzyl






366




CN




4-Trifluoromethylbenzyl






367




CN




2-Methoxybenzyl






368




CN




4-Methoxybenzyl






369




CN




4-tert.-Butoxybenzyl






370




CN




4-Phenoxybenzyl






371




CN




1-Phenethyl






372




CN




2-Phenethyl






373




CN




1-Phenylpropyl






374




CN




2-Phenylpropyl






375




CN




3-Phenylpropyl






376




CN




2-Methyl-2-phenylpropyl






377




CN




2-Methyl-3-phenylpropyl






378




CN




4-Phenylbutyl






379




CN




2-Phenyl-1-ethenyl






380




CN




1-Phenyl-1-ethenyl






381




CN




1-Phenyl-1-propenyl






382




CN




1-Phenyl-1-propen-2-yl






383




CN




2,2-Diphenylethenyl






384




CN




Phenoxymethyl






385




CN




2-Pyridyl






386




CN




3-Pyridyl






387




CN




4-Pyridyl






388




CN




2,6-Pyrimidinyl






389




CN




1,5-Pyrimidinyl






390




CN




2-Thienyl






391




CN




3-Thienyl






392




CN




2-Furyl






393




CN




3-Furyl






394




CN




1-Pyrrolyl






395




CN




1-Imidazolyl






396




CN




1,2,4-Triazolyl






397




CN




1,3,4-Triazolyl






398




CN




4-Thiazolyl






399




CN




2-Benzothiazolyl






400




CN




2-Pyridyloxy






401




CN




2-Pyrimidinyloxy






402




CN




2-Pyridylthio






403




CN




2-Pyrimidinylthio






404




CN




2-Benzothiazolylthio






405




CN




Phenylthiomethyl






406




CN




2-Pyridylmethyl






407




CN




3-Pyridylmethyl






408




CN




Furfuryloxy






409




CN




Thienylmethoxy






410




CN




3-Isoxazolylmethoxy






411




CN




2-Oxazolylmethoxy






412




CN




2-Pyridylmethoxy






413




CN




2′-Furyl-2-ethenyl






414




CN




2′-Thienyl-2-ethenyl






415




CN




3′-Pyridyl-2-ethenyl






416




CN




Oxiranyl






417




CN




1-Aziridinyl






418




CN




1-Azetidinyl






419




CN




1-Pyrrolidinyl






420




CN




2-Tetrahydrofuryl






421




CN




2-Tetrahydropyranyl






422




CN




3-Tetrahydropyranyl






423




CN




1-Piperidinyl






424




CN




1-Morpholinyl






425




CN




1-Piperazinyl






426




CN




1,3-Dioxan-2-yl






427




CN




3-Tetrahydrothiopyranyl






428




CN




2-Dihydropyranyloxy






429




CN




2-Tetrahydropyranyloxy




oil; IR (film): 1205, 1131, 1087, 1047, 1004






430




CN




(CH


2


)


4








431




CN




(CH


2


)


5








432




CN




(CH


2


)


6








433




CN






434




CN













435




CN

























436




CN

























437




CN

























438




CN

























439




CN

























440




CN

























441




CN




CF


3








442




CN




2-Fluoroethyl






443




CN




2,2,2-Trifluoroethyl






444




CN




Pentafluoroethyl






445




CN




Chloromethyl






446




CN




Dichloromethyl






447




CN




Trichloromethyl






448




CN




2-Chloroethyl






449




CN




2,2,2-Trichloroethyl






450




CN




Pentachloroethyl






451




CN




Cyclopropyl






452




CN




Cyclobutyl






453




CN




Cyclopentyl






454




CN




Cyclohexyl






455




CN




1-Methylcyclopropyl






456




CN




2,2-Dimethylcyclopropyl






457




CN




1-Methylcyclohexyl






458




CN




2,2-Difluorocyclopropyl






459




CN




2,2-Dichlorocyclopropyl






460




CN




2,2-Dibromocyclopropyl






461




CN




2,2-Dichloro-3-methylcyclopropyl






462




CN




2,2,3,3-Tetrafluorocyclopropyl






463




CN




Ethenyl






464




CN




1-Propenyl






465




CN




2-Methyl-1-propenyl






466




CN




4-Methylpent-3-en-1-yl






467




CN




2-Propenyl






468




CN




2-Butenyl






469




CN




1-Methyl-2-propenyl






470




CN




3-Methyl-2-butenyl






471




CN




2,2-Difluoroenthenyl






472




CN




2,2-Dichloroenthenyl






473




CN




3,3,3-Trifluoropropenyl






474




CN




3,3,3-Trichloropropenyl






475




CN




3-Chloro-2-propenyl






476




CN




Cyclopent-1-enyl






477




CN




Cyclopentadienyl






478




CN




Cyclohex-1-enyl






479




CN




Pentafluorocyclopentadienyl






480




CN




Pentachlorocyclopentadienyl






481




CN




Styryl






482




CH


3






Methoxymethyl






483




CH


3






Ethoxymethyl






484




CH


3






n-Propoxymethyl






485




CH


3






iso-Propoxymethyl






486




CH


3






tert.-Butoxymethyl






487




CH


3






2-Methoxyprop-2-yl






488




CH


3






2-Ethoxyprop-2-yl






489




CH


3






2-n-Propoxyprop-2-yl






490




CH


3






2-iso-Propoxyprop-2-yl






491




CH


3






2-tert.-Butoxyprop-2-yl






492




CH


3






Methylthiomethyl






493




CH


3






tert.-Butylthiomethyl






494




CH


3






2-Methylthioprop-2-yl






495




CH


3






2-iso-Propylthioprop-2-yl






496




CH


3






2-tert.-Butylthioprop-2-yl






497




CH


3






Methyl






498




CH


3






Ethyl






499




CH


3






n-Propyl






500




CH


3






iso-Propyl






501




CH


3






n-Butyl






502




CH


3






iso-Butyl






503




CH


3






sec.-Butyl






504




CH


3






tert.-Butyl






505




CH


3






n-Hexyl






506




CH


3






n-Decyl






507




CH


3






Cyclopropyl






508




CH


3






Cyclohexyl






509




CH


3






Phenylthiomethyl






510




CH


3






2-Phenylthiomethyl






511




CH


3






2-(2′-Chlorophenylthio)prop-2-yl






512




CH


3






Ethenyl






513




CH


3






1-Propynyl






514




CH


3






Methoxy






515




CH


3






Ethoxy






516




CH


3






n-Propoxy






517




CH


3






iso-Propoxy






518




CH


3






n-Butoxy






519




CH


3






iso-Butoxy






520




CH


3






sec.-Butoxy






521




CH


3






tert.-Butoxy






522




CH


3






Methylthio






523




CH


3






Ethylthio






524




CH


3






n-Propylthio






525




CH


3






iso-Propylthio






526




CH


3






n-Butylthio






527




CH


3






iso-Butylthio






528




CH


3






sec.-Butylthio






529




CH


3






tert.-Butylthio






530




CH


3






Benzylthio






531




CH


3






Trifluoromethoxy






532




CH


3






Cyano






533




CH


3






Amino






534




CH


3






Methylamino






535




CH


3






Dimethylamino






536




CH


3






Ethylamino






537




CH


3






Diethylamino






538




CH


3






Di-n-Propylamino






539




CH


3






Di-iso-Propylamino






540




CH


3






Di-n-Butylamino






541




CH


3






Di-iso-Butylamino






542




CH


3






Acetyl






543




CH


3






Propion-1-yl






544




CH


3






Butyr-1-yl






545




CH


3






iso-Butyr-1-yl






546




CH


3






Pivaloyl






547




CH


3






Benzoyl






548




CH


3






4-Chlorobenzoyl






549




CH


3






Benzoylcarbonyl






550




CH


3






Methoxycarbonyl






551




CH


3






Ethoxycarbonyl






552




CH


3






n-Propoxycarbonyl






553




CH


3






iso-Propoxycarbonyl






554




CH


3






n-Butoxycarbonyl






555




CH


3






iso-Butoxycarbonyl






556




CH


3






sec.-Butoxycarbonyl






557




CH


3






tert.-Butoxycarbonyl






558




CH


3






n-Hexoxycarbonyl






559




CH


3






Phenoxycarbonyl






560




CH


3






4-Chlorophenoxycarbonyl






561




CH


3






Benzyloxycarbonyl






562




CH


3






Aminocarbonyl






563




CH


3






Dimethylaminocarbonyl






564




CH


3






Diethylaminocarbonyl






565




CH


3






Di-iso-Propylaminocarbonyl






566




CH


3






Phenylaminocarbonyl






567




CH


3






N-Methyl-N-Phenylaminocarbonyl






568




CH


3






Phenyl






569




CH


3






2-Fluorophenyl




oil; IR (film): 1708, 1634, 1257, 1129, 761






570




CH


3






3-Fluorophenyl






571




CH


3






4-Fluorophenyl




m. p.: 67-68° C.; IR (KBr): 1691, 1629, 1295, 1253, 1132, 1037, 848






572




CH


3






Pentafluorophenyl






573




CH


3






2-Chlorophenyl




oil; —






574




CH


3






3-Chlorophenyl






575




CH


3






4-Chlorophenyl






576




CH


3






Pentachlorophenyl






577




CH


3






2,3-Dichlorophenyl






578




CH


3






2,4-Dichlorophenyl




oil; IR (film): 1708, 1634, 1256, 1129






579




CH


3






2,5-Dichlorophenyl




m. p.: 80-2° C.; IR (KBr): 1704, 1634, 1250, 1132, 934, 766






580




CH


3






2,6-Dichlorophenyl






581




CH


3






3,4-Dichlorophenyl






582




CH


3






3,5-Dichlorophenyl




m. p.: 87-88° C.; IR (KBr): 1699, 1303, 1071, 1015, 932, 835






583




CH


3






2,3,4-Trichlorophenyl




oil; IR (film): 1709, 1627, 1257, 1131, 1109






584




CH


3






2,3,5-Trichlorophenyl






585




CH


3






2,3,6-Trichlorophenyl






586




CH


3






2,4,5-Trichlorophenyl






587




CH


3






2,4,6-Trichlorophenyl






588




CH


3






3,4,5-Trichlorophenyl






589




CH


3






2,3,4,6-Tetrachlorophenyl






590




CH


3






2,3,5,6-Tetrachlorophenyl






591




CH


3






2-Bromophenyl






592




CH


3






3-Bromophenyl




m. p.: 60-2° C.; IR (KBr): 1708, 1635, 1253, 1129, 1113, 933, 773






593




CH


3






4-Bromophenyl




m. p.: 104-6° C.; IR (KBr): 1694, 1620, 1296, 1264, 1035, 938






594




CH


3






2,4-Dibromophenyl






595




CH


3






3-Bromo-4-Fluorophenyl






596




CH


3






3-Bromo-4-Methoxyphenyl






597




CH


3






2-Iodophenyl






598




CH


3






3-Iodophenyl






599




CH


3






4-Iodophenyl






600




CH


3






2-Chloro-4-fluorophenyl






601




CH


3






2-Chloro-5-fluorophenyl






602




CH


3






2-Chloro-6-fluorophenyl






603




CH


3






2-Chloro-4-bromophenyl






604




CH


3






2-Bromo-4-chlorophenyl






605




CH


3






2-Bromo-4-fluorophenyl






606




CH


3






3-Bromo-4-chlorophenyl






607




CH


3






3-Chloro-4-fluorophenyl






608




CH


3






3-Fluoro-4-chlorophenyl






609




CH


3






2-Cyanophenyl






610




CH


3






3-Cyanophenyl






611




CH


3






4-Cyanophenyl






612




CH


3






2-Nitrophenyl






613




CH


3






3-Nitrophenyl






614




CH


3






4-Nitrophenyl






615




CH


3






2-Methylphenyl






616




CH


3






3-Methylphenyl




oil; IR (film): 1709, 1634, 1256, 1129






617




CH


3






4-Methylphenyl




m. p.: 73-75° C.; IR (KBr): 1696, 1625, 1262, 1127, 1037, 930






618




CH


3






2,4-Dimethylphenyl






619




CH


3






2,6-Dimethylphenyl






620




CH


3






3,4-Dimethylphenyl






621




CH


3






3,5-Dimethylphenyl






622




CH


3






2,3,4-Trimethylphenyl






623




CH


3






2,3,5-Trimethylphenyl






624




CH


3






2,3,6-Trimethylphenyl






625




CH


3






2,4,5-Trimethylphenyl






626




CH


3






2,4,6-Trimethylphenyl






627




CH


3






3,4,5-Trimethylphenyl






628




CH


3






Pentamethylphenyl






629




CH


3






2-Ethylphenyl






630




CH


3






3-Ethylphenyl






631




CH


3






4-Ethylphenyl






632




CH


3






3,5-Diethylphenyl






633




CH


3






2-n-Propylphenyl






634




CH


3






3-n-Propylphenyl






635




CH


3






4-n-Propylphenyl






636




CH


3






2-iso-Propylphenyl






637




CH


3






3-iso-Propylphenyl






638




CH


3






4-iso-Propylphenyl






639




CH


3






2,4-Di-iso-Propylphenyl






640




CH


3






3,5-Di-iso-Propylphenyl






641




CH


3






4-n-Butylphenyl






642




CH


3






4-sec.-Butylphenyl






643




CH


3






4-iso-Butylphenyl






644




CH


3






4-tert.-Butylphenyl






645




CH


3






3-tert.-Butylphenyl






646




CH


3






2-tert.-Butylphenyl






647




CH


3






2,4-Di-tert.-Butylphenyl






648




CH


3






3,5-Di-tert.-Butylphenyl






649




CH


3






4-n-Hexylphenyl






650




CH


3






4-n-Dodecylphenyl






651




CH


3






2-Methyl-4-tert.-Butylphenyl






652




CH


3






2-Methyl-6-tert.-Butylphenyl






653




CH


3






2-Methyl-4-iso-Propylphenyl






654




CH


3






2-Methyl-4-Cyclohexylphenyl






655




CH


3






2-Methyl-4-Phenylphenyl






656




CH


3






2-Methyl-4-Benzylphenyl






657




CH


3






2-Methyl-4-Phenoxyphenyl






658




CH


3






2-Methyl-4-Benzyloxyphenyl






659




CH


3






2-Methyl-3-Chlorophenyl






660




CH


3






2-Methyl-4-Chlorophenyl






661




CH


3






2-Methyl-5-Chlorophenyl






662




CH


3






2-Methyl-6-Chlorophenyl






663




CH


3






2-Methyl-4-Fluorophenyl






664




CH


3






2-Methyl-3-Bromophenyl






665




CH


3






2-Methyl-4-Bromophenyl






666




CH


3






2-Methyl-3-Methoxyphenyl






667




CH


3






2-Methyl-4-Methoxyphenyl






668




CH


3






2-Methyl-5-Methoxyphenyl






669




CH


3






2-Methyl-6-Methoxyphenyl






670




CH


3






2-Methyl-4-iso-Propoxyphenyl






671




CH


3






2-Methyl-2,5-Dimethoxyphenyl






672




CH


3






2-Methoxyphenyl






673




CH


3






3-Methoxyphenyl




oil; IR (film): 1708, 1634, 1285, 1256, 1129, 1111






674




CH


3






4-Methoxyphenyl




oil; IR (film): 1708, 1235, 1129






675




CH


3






2,3-Dimethoxyphenyl






676




CH


3






2,4-Dimethoxyphenyl






677




CH


3






2,5-Dimethoxyphenyl






678




CH


3






2,6-Dimethoxyphenyl






679




CH


3






3,4-Dimethoxyphenyl






680




CH


3






3,5-Dimethoxyphenyl






681




CH


3






3,6-Dimethoxyphenyl






682




CH


3






2,3,4-Trimethoxyphenyl






683




CH


3






2,3,5-Trimethoxyphenyl






684




CH


3






2,3,6-Trimethoxyphenyl






685




CH


3






2,4,5-Trimethoxyphenyl






686




CH


3






2,4,6-Trimethoxyphenyl






687




CH


3






3,4,5-Trimethoxyphenyl






688




CH


3






2-Ethoxyphenyl






689




CH


3






3-Ethoxyphenyl






690




CH


3






4-Ethoxyphenyl






691




CH


3






2-iso-Propoxyphenyl






692




CH


3






3-iso-Propoxyphenyl






693




CH


3






4-iso-Propoxyphenyl






694




CH


3






3-tert.-Butoxyphenyl






695




CH


3






4-tert.-Butoxyphenyl






696




CH


3






2-Trifluoromethoxyphenyl






697




CH


3






3-Trifluoromethoxyphenyl






698




CH


3






4-Trifluoromethoxyphenyl






699




CH


3






3-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl






700




CH


3






4-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl






701




CH


3






2-Chloromethylphenyl






702




CH


3






3-Chloromethylphenyl






703




CH


3






4-Chloromethylphenyl






704




CH


3






2-Trifluoromethylphenyl




oil; IR (film): 1705, 1634, 1313, 1130, 1107, 767






705




CH


3






3-Trifluoromethylphenyl




oil; IR (film): 1710, 1635, 1276, 1128






706




CH


3






4-Trifluoromethylphenyl




m. p.: 104-5° C.; IR (KBr): 1697, 1628, 1323, 1123






707




CH


3






2-(Methoxyiminomethyl)phenyl






708




CH


3






3-(Methoxyiminomethyl)phenyl






709




CH


3






4-(Methoxyiminomethyl)phenyl






710




CH


3






2-(Ethoxyiminomethyl)phenyl






711




CH


3






3-(Ethoxyiminomethyl)phenyl






712




CH


3






4-(Ethoxyiminomethyl)phenyl






713




CH


3






2-(n-Propoxyiminomethyl)phenyl






714




CH


3






3-(n-Propoxyiminomethyl)phenyl






715




CH


3






4-(n-Propoxyiminomethyl)phenyl






716




CH


3






2-(iso-Propoxyiminomethyl)phenyl






717




CH


3






3-(iso-Propoxyiminomethyl)phenyl






718




CH


3






4-(iso-Propoxyiminomethyl)phenyl






719




CH


3






2-(n-Butoxyiminomethyl)phenyl






720




CH


3






3-(n-Butoxyiminomethyl)phenyl






721




CH


3






4-(n-Butoxyiminomethyl)phenyl






722




CH


3






2-(iso-Butoxyiminomethyl)phenyl






723




CH


3






3-(iso-Butoxyiminomethyl)phenyl






724




CH


3






4-(iso-Butoxyiminomethyl)phenyl






725




CH


3






2-(tert.-Butoxyiminomethyl)phenyl






726




CH


3






3-(tert.-Butoxyiminomethyl)phenyl






727




CH


3






4-(tert.-Butoxyiminomethyl)phenyl






728




CH


3






2-(n-Pentoxyiminomethyl)phenyl






729




CH


3






3-(n-Pentoxyiminomethyl)phenyl






730




CH


3






4-(n-Pentoxyiminomethyl)phenyl






731




CH


3






2-(n-Hexoxyiminomethyl)phenyl






732




CH


3






3-(n-Hexoxyiminomethyl)phenyl






733




CH


3






4-(n-Hexoxyiminomethyl)phenyl






734




CH


3






2-(Allyloxyiminomethyl)phenyl






735




CH


3






3-(Allyloxyiminomethyl)phenyl






736




CH


3






4-(Allyloxyiminomethyl)phenyl






737




CH


3






2-(Benzyloxyiminomethyl)phenyl






738




CH


3






3-(Benzyloxyiminomethyl)phenyl






739




CH


3






4-(Benzyloxyiminomethyl)phenyl






740




CH


3






2-(Methoxyimino-1′-ethyl)phenyl






741




CH


3






3-(Methoxyimino-1′-ethyl)phenyl






742




CH


3






4-(Methoxyimino-1′-ethyl)phenyl






743




CH


3






2-(Ethoxyimino-1′-ethyl)phenyl






744




CH


3






3-(Ethoxyimino-1′-ethyl)phenyl






745




CH


3






4-(Ethoxyimino-1′-ethyl)phenyl






746




CH


3






2-(n-Propoxyimino-1′-ethyl)phenyl






747




CH


3






3-(n-Propoxyimino-1′-ethyl)phenyl






748




CH


3






4-(n-Propoxyimino-1′-ethyl)phenyl






749




CH


3






2-(n-Butoxyimino-1′-ethyl)phenyl






750




CH


3






3-(n-Butoxyimino-1′-ethyl)phenyl






751




CH


3






4-(n-Butoxyimino-1′-ethyl)phenyl






752




CH


3






2-(n-Pentoxyimino-1′-ethyl)phenyl






753




CH


3






3-(n-Pentoxyimino-1′-ethyl)phenyl






754




CH


3






4-(n-Pentoxyimino-1′-ethyl)phenyl






755




CH


3






2-(n-Hexoxyimino-1′-ethyl)phenyl






756




CH


3






3-(n-Hexoxyimino-1′-ethyl)phenyl






757




CH


3






4-(n-Hexoxyimino-1′-ethyl)phenyl






758




CH


3






2-(Allyloxyimino-1′-ethyl)phenyl






759




CH


3






3-(Allyloxyimino-1′-ethyl)phenyl






760




CH


3






4-(Allyloxyimino-1′-ethyl)phenyl






761




CH


3






2-(Benzyloxyimino-1′-ethyl)phenyl






762




CH


3






3-(Benzyloxyimino-1′-ethyl)phenyl






763




CH


3






4-(Benzyloxyimino-1′-ethyl)phenyl






764




CH


3






2-Phenylphenyl






765




CH


3






3-Phenylphenyl






766




CH


3






4-Phenylphenyl






767




CH


3






2-Phenoxyphenyl






768




CH


3






3-Phenoxyphenyl






769




CH


3






4-Phenoxyphenyl




oil; IR (film): 1708, 1489, 1240, 1129






770




CH


3






2-Benzyloxyphenyl






771




CH


3






3-Benzyloxyphenyl






772




CH


3






4-Benzyloxyphenyl






773




CH


3






4-(Imidazol-1′-yl)phenyl






774




CH


3






4-(Piperazin-1′-yl)phenyl






775




CH


3






4-(Morpholin-1′-yl)phenyl






776




CH


3






4-(Piperidin-1′-yl)phenyl






777




CH


3






4-(Pyridyl-1′-yl)phenyl






778




CH


3






2-Cyclopropylphenyl






779




CH


3






3-Cyclopropylphenyl






780




CH


3






4-Cyclopropylphenyl






781




CH


3






3-Cyclohexylphenyl






782




CH


3






4-Cyclohexylphenyl






783




CH


3






4-Oxiranylphenyl






784




CH


3






4-(1′,3′-Dioxan-2′-yl)phenyl






785




CH


3






4-(Tetrahydropyran-2-yloxy)phenyl






786




CH


3






1-Naphthyl






787




CH


3






2-Naphthyl






788




CH


3






9-Anthryl






789




CH


3






1-Naphthoxy






790




CH


3






2-Naphthoxy






791




CH


3






9-Anthroxy






792




CH


3






Phenoxy






793




CH


3






2-Chlorophenoxy






794




CH


3






3-Chlorophenoxy






795




CH


3






4-Chlorophenoxy






796




CH


3






4-Methylphenoxy






797




CH


3






4-tert.-Butylphenoxy






798




CH


3






4-Methoxyphenoxy






799




CH


3






4-Ethoxyphenoxy






800




CH


3






4-tert.-Butoxyphenoxy






801




CH


3






Phenylthio






802




CH


3






2-Chlorophenylthio






803




CH


3






4-Chlorophenylthio






804




CH


3






Benzyl






805




CH


3






2-Methylbenzyl






806




CH


3






3-Methylbenzyl






807




CH


3






4-Methylbenzyl






808




CH


3






4-tert.-Butylbenzyl






809




CH


3






2-Chlorobenzyl






810




CH


3






3-Chlorobenzyl






811




CH


3






4-Chlorobenzyl






812




CH


3






2,4-Dichlorobenzyl






813




CH


3






2,6-Dichlorobenzyl






814




CH


3






2,4,6-Trichlorobenzyl






815




CH


3






2-Trifluoromethylbenzyl






816




CH


3






3-Trifluoromethylbenzyl






817




CH


3






4-Trifluoromethylbenzyl






818




CH


3






2-Methoxybenzyl






819




CH


3






4-Methoxybenzyl






820




CH


3






4-tert.-Butoxybenzyl






821




CH


3






4-Phenoxybenzyl






822




CH


3






1-Phenethyl






823




CH


3






2-Phenethyl






824




CH


3






1-Phenylpropyl






825




CH


3






2-Phenylpropyl






826




CH


3






3-Phenylpropyl






827




CH


3






2-Methyl-2-phenylpropyl






828




CH


3






2-Methyl-3-phenylpropyl






829




CH


3






4-Phenylbutyl






830




CH


3






2-Phenyl-1-ethenyl






831




CH


3






1-Phenyl-1-ethenyl






832




CH


3






1-Phenyl-1-propenyl






833




CH


3






1-Phenyl-1-propen-2-yl






834




CH


3






2,3-Diphenylethenyl






835




CH


3






Phenoxymethyl






836




CH


3






2-Pyridyl






837




CH


3






3-Pyridyl






838




CH


3






4-Pyridyl






839




CH


3






2,6-Pyrimidienyl






840




CH


3






1,5-Pyrimidienyl






841




CH


3






2-Thienyl






842




CH


3






3-Thienyl






843




CH


3






2-Furyl






844




CH


3






3-Furyl






845




CH


3






1-Pyrrolyl






846




CH


3






1-Imidazolyl






847




CH


3






1,2,4-Triazolyl






848




CH


3






1,3,4-Triazolyl






849




CH


3






4-Thiazolyl






850




CH


3






3-Benzothiazolyl






851




CH


3






2-Pyridyloxy






852




CH


3






2-Pyrimidinyloxy






853




CH


3






2-Pyridylthio






854




CH


3






2-Pyrimidinylthio






855




CH


3






2-Benzothiazolylthio






856




CH


3






Phenylthiomethyl






857




CH


3






2-Pyridylmethyl






858




CH


3






3-Pyridylmethyl






859




CH


3






Furfuryloxy






860




CH


3






Thienylmethoxy






861




CH


3






3-Isoazolylmethoxy






862




CH


3






2-Oxazolylmethoxy






863




CH


3






2-Pyridylmethoxy






864




CH


3






2′-Furyl-2-ethenyl






865




CH


3






2′-Thienyl-2-ethenyl






866




CH


3






3′-Pyridyl-2-ethenyl






867




CH


3






Oziranyl






868




CH


3






1-Aziridinyl






869




CH


3






1-Azetidinyl






870




CH


3






1-Pyrrolidinyl






871




CH


3






2-Tetrahydrofuryl






872




CH


3






2-Tetrahydropyranyl






873




CH


3






3-Tetrahydropyranyl






874




CH


3






1-Piperidinyl






875




CH


3






1-Morpholinyl






876




CH


3






1-Piperazinyl






877




CH


3






1,3-Dioxan-2-yl






878




CH


3






3-Tetrahydrothiopyranyl






879




CH


3






2-Dihydropyranyloxy






880




CH


3






2-Tetrahydropyranyloxy






881




CH


3






CF


3








882




CH


3






2-Fluoroethyl






883




CH


3






2,2,2-Trifluoroethyl






884




CH


3






Pentafluoroethyl






885




CH


3






Chloromethyl






886




CH


3






Dichloromethyl






887




CH


3






Trichloromethyl






888




CH


3






2-Chloroethyl






889




CH


3






2,2,2-Trichloroethyl






890




CH


3






Pentachloroethyl






891




CH


3






Cyclopropyl






892




CH


3






Cyclobutyl






893




CH


3






Cyclopentyl






894




CH


3






Cyclohexyl






895




CH


3






1-Methylcyclopropyl






896




CH


3






2,2-Dimethylcyclopropyl






897




CH


3






1-Methylcyclohexyl






898




CH


3






2,2-Difluorocyclopropyl






899




CH


3






2,2-Dichlorocyclopropyl






900




CH


3






2,2-Dibromocyclopropyl






901




CH


3






2,2-Dichloro-3-methylcyclopropyl






902




CH


3






2,2,3,3-Tetrafluorocyclobutyl






903




CH


3






Ethenyl






904




CH


3






1-Propenyl






905




CH


3






2-Methyl-1-propenyl






906




CH


3






4-Methylpent-3-en-1-yl






907




CH


3






2-Propenyl






908




CH


3






2-Butenyl






909




CH


3






1-Methyl-2-propenyl






910




CH


3






3-Methyl-2-butenyl






911




CH


3






2,2-Difluoroethenyl






912




CH


3






2,2-Dichloroethenyl






913




CH


3






3,3,3-Trifluoropropenyl






914




CH


3






3,3,3-Trichloropropenyl






915




CH


3






3-Chloro-2-propenyl






916




CH


3






Cyclopent-1-enyl






917




CH


3






Cyclopentadienyl






918




CH


3






Cyclohex-1-enyl






919




CH


3






Pentafluorocyclopentadienyl






920




CH


3






Pentachlorocyclopentadienyl






921




Phenyl




Phenyl






922




Phenyl




2-Fluorophenyl






923




Phenyl




4-Fluorophenyl






924




Phenyl




2-Chlorophenyl






925




Phenyl




3-Chlorophenyl






926




Phenyl




4-Chlorophenyl






927




Phenyl




3,4-Dichlorophenyl






928




Phenyl




4-Nitrophenyl






929




Phenyl




2-CF


3


-Phenyl






930




Phenyl




3-CF


3


-Phenyl






931




Phenyl




4-CF


3


-Phenyl






932




Phenyl




2-Methylphenyl






933




Phenyl




3-Methylphenyl






934




Phenyl




4-Methylphenyl






935




Phenyl




2,4-Dimethylphenyl






936




Phenyl




4-tert.-Butylphenyl






937




Phenyl




4-Methoxyphenyl






938




4-Fluorophenyl




4-Fluorophenyl






939




2-Fluorophenyl




4-Fluorophenyl






940




2-Chlorophenyl




4-Fluorophenyl






941




2-Chlorophenyl




2-Chlorophenyl






942




3-Chlorophenyl




3-Chlorophenyl






943




4-Chlorophenyl




4-Chlorophenyl






944




2-Chlorophenyl




4-Chlorophenyl






945




4-Methoxyphenyl




4-Methoxyphenyl






946




4-Dimethylaminophenyl




4-Dimethylaminophenyl






947




Phenyl




Naphthyl






948




Ethyl




Ethyl






949




Ethyl




n-Propyl






950




Ethyl




iso-Propyl






951




Ethyl




n-Butyl






952




Ethyl




iso-Butyl






953




Ethyl




2-Methyl-butyl






954




Ethyl




Benzyl






955




n-Propyl




n-Propyl






956




iso-Propyl




iso-Propyl






957




n-Butyl




n-Butyl






958




iso-Butyl




iso-Butyl






959




tert.-Butyl




tert.-Butyl






960




Benzyl




Benzyl






961




Pentachloroethyl




Pentachloroethyl






962




n-Hexyl




n-Hexyl






963




Ethoxycarbonyl




Ethoxycarbonyl






964




Phenyl




Benzoyl






965




Ethyl




Phenyl






966




n-Butyl




Phenyl






967




Styryl




Styryl






968




2-Pyridyl




2-Pyridyl






969




3-Pyridyl




3-Pyridyl






970




CH


3






3,5-Dibenzyloxyphenyl




IR (film): 1707, 1581, 1256, 1157, 1129






















TABLE II








































No.




R


3






R


4






Data

















1




Cl




Phenyl







2




Cl




Cyano






3




Cl




Ethoxycarbonyl






4




Cl




Cyclopropyl






5




CF


3






CF


3








6




CF


3






Phenyl






7




CCl


3






CCl


3








8




CCl


3






Phenyl






9




CH


2


Cl




Phenyl






10




CF


2


CF


3






Phenyl






11




CF


2


Cl




Phenyl






12




CHCl


2






Phenyl






13




Cyclopropyl




Cyclopropyl






14




Cyclopropyl




Phenyl




oil; IR (film): 1437, 1321, 1219, 1045, 983, 766






15




Cyclopropyl




4-Fluorophenyl




oil; IR (film): 1508, 1321, 1222, 1046, 985, 839






16




Cyclopropyl




4-Chlorophenyl




oil; IR (film): 1489, 1321, 1218, 1090, 1046, 829






17




Cyclopropyl




4-Methoxyphenyl




oil; IR (film): 1300, 1250, 1218, 983, 833






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




m.p.: 83° C.;









IR (KBr): 1437, 1223, 1206, 1069, 1006






37




CN




2-Ethoxyprop-2-yl




oil; IR (film): 1439, 3122, 1221, 1202, 1048






38




CN




2-n-Propoxyprop-2-yl




oil; IR (film): 1438, 1322, 1221, 1203, 1048






39




CN




2-iso-Propoxyprop-2-yl




m.p.: 74-5° C.;









IR (KBr): 1302, 1231, 1169, 1108, 1079, 997, 757






40




CN




2-tert.-Butoxyprop-2-yl






41




CN




Methylthiomethyl






42




CN




tert.-Butylthiomethyl






43




CN




2-Methylthioprop-2-yl




m.p.: 107° C.;









IR (KBr): 1434, 1297, 1126, 1066, 1010, 769






44




CN




2-iso-Propylthioprop-2-yl




oil; IR (film): 1438, 1366, 1321, 1221, 1202






45




CN




2-tert.-Butylthioprop-2-yl






46




CN




Methyl






47




CN




Ethyl






48




CN




n-Propyl






49




CN




iso-Propyl




oil; IR (film): 1439, 1321, 1222, 1012, 767






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




m.p.: 74-75° C.; IR (KBr): 1433, 1223, 1043, 763






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




Methoxycarbonyl






100




CN




Ethoxycarbonyl






101




CN




n-Propoxycarbonyl






102




CN




iso-Propoxycarbonyl






103




CN




n-Butoxycarbonyl






104




CN




iso-Butoxycarbonyl






105




CN




sec.-Butoxycarbonyl






106




CN




tert.-Butoxycarbonyl






107




CN




n-Hexoxycarbonyl






108




CN




Phenoxycarbonyl






109




CN




4-Chlorophenoxycarbonyl






110




CN




Benzyloxycarbonyl






111




CN




Aminocarbonyl






112




CN




Dimethylaminocarbonyl






113




CN




Diethylaminocarbonyl






114




CN




Di-iso-Propylaminocarbonyl






115




CN




Phenylaminocarbonyl






116




CN




N-Methyl-N-Phenylaminocarbonyl






117




CN




Phenyl




m.p.: 99-100° C.;









IR (KBr): 1436, 1215, 1208, 1097, 1026, 944, 766, 690






118




CN




2-Fluorophenyl






119




CN




3-Fluorophenyl






120




CN




4-Fluorophenyl






121




CN




Pentafluorophenyl






122




CN




2-Chlorophenyl






123




CN




3-Chlorophenyl






124




CN




4-Chlorophenyl






125




CN




Pentachlorophenyl






126




CN




2,3-Dichlorophenyl






127




CN




2,4-Dichlorophenyl






128




CN




2,5-Dichlorophenyl






129




CN




2,6-Dichlorophenyl






130




CN




3,4-Dichlorophenyl






131




CN




3,5-Dichlorophenyl






132




CN




2,3,4-Trichlorophenyl






133




CN




2,3,5-Trichlorophenyl






134




CN




2,3,6-Trichlorophenyl






135




CN




2,4,5-Trichlorophenyl






136




CN




2,4,6-Trichlorophenyl






137




CN




3,4,5-Trichlorophenyl






138




CN




2,3,4,6-Tetrachlorophenyl






139




CN




2,3,5,6-Tetrachlorophenyl






140




CN




2-Bromophenyl






141




CN




3-Bromophenyl






142




CN




4-Bromophenyl






143




CN




2,4-Dibromophenyl






144




CN




3-Bromo-4-fluorophenyl






145




CN




3-Bromo-4-methoxyphenyl






146




CN




2-Iodophenyl






147




CN




3-Iodophenyl






148




CN




4-Iodophenyl






149




CN




2-Chloro-4-fluorophenyl






150




CN




2-Chloro-5-fluorophenyl






151




CN




2-Chloro-6-fluorophenyl






152




CN




2-Chloro-4-bromophenyl






153




CN




2-Bromo-4-chlorophenyl






154




CN




2-Bromo-4-fluorophenyl






155




CN




3-Bromo-4-chlorophenyl






156




CN




3-Chloro-4-fluorophenyl






157




CN




3-Fluoro-4-chlorophenyl






158




CN




2-Cyanophenyl






159




CN




3-Cyanophenyl






160




CN




4-Cyanophenyl






161




CN




2-Nitrophenyl






162




CN




3-Nitrophenyl






163




CN




4-Nitrophenyl






164




CN




2-Methylphenyl






165




CN




3-Methylphenyl






166




CN




4-Methylphenyl






167




CN




2,4-Dimethylphenyl






168




CN




2,6-Dimethylphenyl






169




CN




3,4-Dimethylphenyl






170




CN




3,5-Dimethylphenyl






171




CN




2,3,4-Trimethylphenyl






172




CN




2,3,5-Trimethylphenyl






173




CN




2,3,6-Trimethylphenyl






174




CN




2,4,5-Trimethylphenyl






175




CN




2,4,6-Trimethylphenyl






176




CN




3,4,5-Trimethylphenyl






177




CN




Pentamethylphenyl






178




CN




2-Ethylphenyl






179




CN




3-Ethylphenyl






180




CN




4-Ethylphenyl






181




CN




3,5-Diethylphenyl






182




CN




2-n-Propylphenyl






183




CN




3-n-Propylphenyl






184




CN




4-n-Propylphenyl






185




CN




2-iso-Propylphenyl






186




CN




3-iso-Propylphenyl






187




CN




4-iso-Propylphenyl






188




CN




2,4-Di-iso-Propylphenyl






189




CN




3,5-Di-iso-Propylphenyl






190




CN




4-n-Butylphenyl






191




CN




4-sec.-Butylphenyl






192




CN




4-iso-Butylphenyl






193




CN




4-tert.-Butylphenyl






194




CN




3-tert.-Butylphenyl






195




CN




2-tert.-Butylphenyl






196




CN




2,4-Di-tert.-Butylphenyl






197




CN




3,5-Di-tert.-Butylphenyl






198




CN




4-n-Hexylphenyl






199




CN




4-n-Dodecylphenyl






200




CN




2-Methyl-4-tert.-Butylphenyl






201




CN




2-Methyl-6-tert.-Butylphenyl






202




CN




2-Methyl-4-iso-Propylphenyl






203




CN




2-Methyl-4-Cyclohexylphenyl






204




CN




2-Methyl-4-Phenylphenyl






205




CN




2-Methyl-4-Benxylphenyl






206




CN




2-Methyl-4-Phenoxyphenyl






207




CN




2-Methyl-4-Benxyloxyphenyl






208




CN




2-Methyl-3-Chlorophenyl






209




CN




2-Methyl-4-Chlorophenyl






210




CN




2-Methyl-5-Chlorophenyl






211




CN




2-Methyl-6-Chlorophenyl






212




CN




2-Methyl-4-Fluorophenyl






213




CN




2-Methyl-3-Bromophenyl






214




CN




2-Methyl-4-Bromophenyl






215




CN




2-Methyl-3-Methoxyphenyl






216




CN




2-Methyl-4-Methoxyphenyl






217




CN




2-Methyl-5-Methoxyphenyl






218




CN




2-Methyl-6-Methoxyphenyl






219




CN




2-Methyl-4-iso-Propoxyphenyl






220




CN




2-Methyl-2-,5-Dimethoxyphenyl






221




CN




2-Methoxyphenyl






222




CN




3-Methoxyphenyl






223




CN




4-Methoxyphenyl






224




CN




2,3-Dimethoxyphenyl






225




CN




2,4-Dimethoxyphenyl






226




CN




2,5-Dimethoxyphenyl






227




CN




2,6-Dimethoxyphenyl






228




CN




3,4-Dimethoxyphenyl






229




CN




3,5-Dimethoxyphenyl






230




CN




3,6-Dimethoxyphenyl






231




CN




2,3,4-Trimethoxyphenyl






232




CN




2,3,5-Trimethoxyphenyl






233




CN




2,3,6-Trimethoxyphenyl






234




CN




2,4,5-Trimethoxyphenyl






235




CN




2,4,6-Trimethoxyphenyl






236




CN




3,4,5-Trimethoxyphenyl






237




CN




2-Ethoxyphenyl






238




CN




3-Ethoxyphenyl






239




CN




4-Ethoxyphenyl






240




CN




2-iso-Propoxyphenyl






241




CN




3-iso-Propoxyphenyl






242




CN




4-iso-Propoxyphenyl






243




CN




3-tert.-Butoxyphenyl






244




CN




4-tert.-Butoxyphenyl






245




CN




2-Trifluoromethoxyphenyl






246




CN




3-Trifluoromethoxyphenyl






247




CN




4-Trifluoromethoxyphenyl






248




CN




3-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl






249




CN




4-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl






250




CN




2-Chloromethylphenyl






251




CN




3-Chloromethylphenyl






252




CN




4-Chloromethylphenyl






253




CN




2-Trifluoromethylphenyl






254




CN




3-Trifluoromethylphenyl






255




CN




4-Trifluoromethylphenyl






256




CN




2-(Methoxyiminomethyl)phenyl






257




CN




3-(Methoxyiminomethyl)phenyl






258




CN




4-(Methoxyiminomethyl)phenyl






259




CN




2-(Ethoxyiminomethyl)phenyl






260




CN




3-(Ethoxyiminomethyl)phenyl






261




CN




4-(Ethoxyiminomethyl)phenyl






262




CN




2-(n-Propoxyiminomethyl)phenyl






263




CN




3-(n-Propoxyiminomethyl)phenyl






264




CN




4-(n-Propoxyiminomethyl)phenyl






265




CN




2-(iso-Propoxyiminomethyl)phenyl






266




CN




3-(iso-Propoxyiminomethyl)phenyl






267




CN




4-(iso-Propoxyiminomethyl)phenyl






268




CN




2-(n-Butoxyiminomethyl)phenyl






269




CN




3-(n-Butoxyiminomethyl)phenyl






270




CN




4-(n-Butoxyiminomethyl)phenyl






271




CN




2-(iso-Butoxyiminomethyl)phenyl






272




CN




3-(iso-Butoxyiminomethyl)phenyl






273




CN




4-(iso-Butoxyiminomethyl)phenyl






274




CN




2-(tert.-Butoxyiminomethyl)phenyl






275




CN




3-(tert.-Butoxyiminomethyl)phenyl






276




CN




4-(tert.-Butoxyiminomethyl)phenyl






277




CN




2-(n-Pentoxyiminomethyl)phenyl






278




CN




3-(n-Pentoxyiminomethyl)phenyl






279




CN




4-(n-Pentoxyiminomethyl)phenyl






280




CN




2-(n-Hexoxyiminomethyl)phenyl






281




CN




3-(n-Hexoxyiminomethyl)phenyl






282




CN




4-(n-Hexoxyiminomethyl)phenyl






283




CN




2-(Allyloxyiminomethyl)phenyl






284




CN




3-(Allyloxyiminomethyl)phenyl






285




CN




4-(Allyloxyiminomethyl)phenyl






286




CN




2-(Benzyloxyiminomethyl)phenyl






287




CN




3-(Benzyloxyiminomethyl)phenyl






288




CN




4-(Benzyloxyiminomethyl)phenyl






289




CN




2-(Methoxyimino-1′-ethyl)phenyl






290




CN




3-(Methoxyimino-1′-ethyl)phenyl






219




CN




4-(Methoxyimino-1′-ethyl)phenyl






292




CN




2-(Ethoxyimino-1′-ethyl)phenyl






293




CN




3-(Ethoxyimino-1′-ethyl)phenyl






294




CN




4-(Ethoxyimino-1′-ethyl)phenyl






295




CN




2-(n-Propoxyimino-1′-ethyl)phenyl






296




CN




3-(n-Propoxyimino-1′-ethyl)phenyl






297




CN




4-(n-Propoxyimino-1′-ethyl)phenyl






298




CN




2-(n-Butoxyamino-1′-ethyl)phenyl






299




CN




3-(n-Butoxyamino-1′-ethyl)phenyl






300




CN




4-(n-Butoxyamino-1′-ethyl)phenyl






301




CN




2-(n-Pentoxyimino-1′-ethyl)phenyl






302




CN




3-(n-Pentoxyimino-1′-ethyl)phenyl






303




CN




4-(n-Pentoxyimino-1′-ethyl)phenyl






304




CN




2-(n-Hexoxyimino-1′-ethyl)phenyl






305




CN




3-(n-Hexoxyimino-1′-ethyl)phenyl






306




CN




4-(n-Hexoxyimino-1′-ethyl)phenyl






307




CN




2-(Allyloxyimino-1′-ethyl)phenyl






308




CN




3-(Allyloxyimino-1′-ethyl)phenyl






309




CN




4-(Allyloxyimino-1′-ethyl)phenyl






310




CN




2-(Benzyloxyimino-1′-ethyl)phenyl






311




CN




3-(Benzyloxyimino-1′-ethyl)phenyl






312




CN




4-(Benzyloxyimino-1′-ethyl)phenyl






313




CN




2-Phenylphenyl






314




CN




3-Phenylphenyl






315




CN




4-Phenylphenyl






316




CN




2-Phenoxyphenyl






317




CN




3-Phenoxyphenyl






318




CN




4-Phenoxyphenyl






319




CN




2-Benzyloxyphenyl






320




CN




3-Benzyloxyphenyl






321




CN




4-Benzyloxyphenyl






322




CN




4-(Imidazol-1′-yl)phenyl






323




CN




4-(Piperazin-1′-yl)phenyl






324




CN




4-(Morpholin-1′-yl)phenyl






325




CN




4-(Piperdin-1′-yl)phenyl






326




CN




4-(Pyridyl-2′-oxy)phenyl






327




CN




2-Cyclopropylphenyl






328




CN




3-Cyclopropylphenyl






329




CN




4-Cyclopropylphenyl






330




CN




3-Cyclohexylphenyl






331




CN




4-Cyclohexylphenyl






332




CN




4-Oxiranylphenyl






333




CN




4-(1′,3′-Dioxan-2′-yl)phenyl






334




CN




4-(Tetrahydropyran-2-yloxy)phenyl






335




CN




1-Naphthyl






336




CN




2-Naphthyl






337




CN




9-Anthryl






338




CN




1-Naphthoxy






339




CN




2-Naphthoxy






340




CN




9-Anthroxy






341




CN




Phenoxy






342




CN




2-Chlorophenoxy






343




CN




3-Chlorophenoxy






344




CN




4-Chlorophenoxy






345




CN




4-Methylphenoxy






346




CN




4-tert.-Butylphenoxy






347




CN




4-Methoxyphenoxy






348




CN




4-Ethoxyphenoxy






349




CN




4-tert.-Butoxyphenoxy






350




CN




Phenylthio






351




CN




2-Chlorophenylthio






352




CN




4-Chlorophenylthio






353




CN




Benzyl






354




CN




2-Methylbenzyl






355




CN




3-Methylbenzyl






356




CN




4-Methylbenzyl






357




CN




4-tert.-Butylbenzyl






358




CN




2-Chlorobenzyl






359




CN




3-Chlorobenzyl






360




CN




4-Chlorobenzyl






361




CN




2,4-Dichlorobenzyl






362




CN




2,6-Dichlorobenzyl






363




CN




2,4,6-Trichlorobenzyl






364




CN




2-Trifluoromethylbenzyl






365




CN




3-Trifluoromethylbenzyl






366




CN




4-Trifluoromethylbenzyl






367




CN




2-Methoxybenzyl






368




CN




4-Methoxybenzyl






369




CN




4-tert.-Butoxybenzyl






370




CN




4-Phenoxybenzyl






371




CN




1-Phenethyl






372




CN




2-Phenethyl






373




CN




1-Phenylpropyl






374




CN




2-Phenylpropyl






375




CN




3-Phenylpropyl






376




CN




2-Methyl-2-phenylpropyl






377




CN




2-Methyl-3-phenylpropyl






378




CN




4-Phenylbutyl






379




CN




2-Phenyl-1-ethenyl






380




CN




1-Phenyl-1-ethenyl






381




CN




1-Phenyl-1-propenyl






382




CN




1-Phenyl-1-propen-2-yl






383




CN




2,2-Diphenylethenyl






384




CN




Phenoxymethyl






385




CN




2-Pyridyl






386




CN




3-Pyridyl






387




CN




4-Pyridyl






388




CN




2,6-Pyrimidinyl






389




CN




1,5-Pyrimidinyl






390




CN




2-Thienyl






391




CN




3-Thienyl






392




CN




2-Furyl






393




CN




3-Furyl






394




CN




1-Pyrrolyl






395




CN




1-Imidazolyl






396




CN




1,2,4-Trimzolyl






397




CN




1,3,4-Triazolyl






398




CN




4-Thiazolyl






399




CN




2-Benzothiazolyl






400




CN




2-Pyridyloxy






401




CN




2-Pyrimidimyloxy






402




CN




2-Pyridylthio






403




CN




2-Pyrimidimylthio






404




CN




2-Benzothiazolythio






405




CN




Phenylthiomethyl






406




CN




2-Pyridylmethyl






407




CN




3-Pyridylmethyl






408




CN




Ferfuryloxy






409




CN




Thienylmethoxy






410




CN




3-Isozazolylmethoxy






411




CN




2-Oxazolylmethoxy






412




CN




2-Pyridylmethoxy






413




CN




2′-Furyl-2-ethenyl






414




CN




2′-Thienyl-2-ethenyl






415




CN




3′-Pyridyl-2-ethenyl






416




CN




Oxionyl






417




CN




1-Aziridinyl






418




CN




1-Azoxidinyl






419




CN




1-Pyrrolidinyl






420




CN




2-Tetrahydrofuryl






421




CN




2-Tetrahydropyranyl






422




CN




3-Tetrahydropyranyl






423




CN




1-Piperidinyl






424




CN




1-Morphotinyl






425




CN




1-Piperazinyl






426




CN




1,3-Dioxan-2-yl






427




CN




3-Tetrahydrothiopyranyl






428




CN




2-Dihydropyranyloxy






429




CN




2-Tetrahydrophyranyloxy




oil; IR (film): 1439, 1228, 1209, 1050, 1025, 767






430




CN




(CH


2


)


4








431




CN




(CH


2


)


5








432




CN




(CH


2


)


6








433




CN






434




CN













435




CN

























436




CN

























437




CN

























438




CN

























439




CN

























440




CN

























441




CN




CF


3








442




CN




2-Fluoroethyl






443




CN




2,2,2-Trifluoroethyl






444




CN




Pentafluoroethyl






445




CN




Chloromethyl






446




CN




Dichloromethyl






447




CN




Trichloromethyl






448




CN




2-Chloroethyl






449




CN




2,2,2-Trichloroethyl






450




CN




Pentachloroethyl






451




CN




Cyclopropyl






452




CN




Cyclobutyl






453




CN




Cyclopenyl






454




CN




Cyclohexyl






455




CN




1-Methylcyclopropyl






456




CN




2,2-Dimethylcyclopropyl






457




CN




1-Methylcyclohexyl






458




CN




2,2-Difluorocyclopropyl






459




CN




2,2-Dichlorocyclopropyl






460




CN




2,2-Dibromocyclopropyl






461




CN




2,2-Dichloro-3-Methylcyclopropyl






462




CN




2,2,3,3-Tetrafluorocyclobutyl






463




CN




Ethenyl






464




CN




1-Propenyl






465




CN




2-Methyl-1-propenyl






466




CN




4-Methylpent-3-en-1-yl






467




CN




2-Propenyl






468




CN




2-Butenyl






469




CN




1-Methyl-2-propenyl






470




CN




3-Methyl-2-butenyl






471




CN




2,2-Difluoroethenyl






472




CN




2,2-Dichloroethenyl






473




CN




3,3,3-Trifluoropropenyl






474




CN




3,3,3-Trichloropropenyl






475




CN




3-Chloro-2-propenyl






476




CN




Cyclopent-1-enyl






477




CN




Cyclopentadienyl






478




CN




Cyclohex-1-enyl






479




CN




Pentafluorocyclopentadienyl






480




CN




Pentachlorocyclopentadienyl






481




CN




Styryl






482




CH


3






Methoxymethyl






483




CH


3






Ethoxymethyl






484




CH


3






n-Propoxymethyl






485




CH


3






iso-Propoxymethyl






486




CH


3






tert.-Butoxymethyl






487




CH


3






2-Methoxyprop-2-yl






488




CH


3






2-Ethoxyprop-2-yl






489




CH


3






2-n-Propoxyprop-2-yl






490




CH


3






2-iso-Propoxyprop-2-yl






491




CH


3






2-tert.-Butoxyprop-2-yl






492




CH


3






Methylthiomethyl






493




CH


3






tert.-Butylthiomethyl






494




CH


3






2-Methylthioprop-2-yl






495




CH


3






2-iso-Propylthioprop-2-yl






496




CH


3






2-tert.-Butylthioprop-2-yl






497




CH


3






Methyl




m.p. 68-71° C.; IR (KBr): 1137, 1298, 1067, 1023, 1007, 771






498




CH


3






Ethyl






499




CH


3






n-Propyl






500




CH


3






iso-Propyl






501




CH


3






n-Butyl






502




CH


3






iso-Butyl






503




CH


3






sec.-Butyl






504




CH


3






tert.-Butyl






505




CH


3






n-Hexyl






506




CH


3






n-Decyl






507




CH


3






Cyclopropyl






508




CH


3






Cyclohexyl






509




CH


3






Phenylthiomethyl






510




CH


3






2-Phenylthiomethyl






511




CH


3






2-(2′-Chlorophenylthio)prop-2-yl)






512




CH


3






Ethynyl






513




CH


3






1-Propynyl






514




CH


3






Methoxy






515




CH


3






Ethoxy






516




CH


3






n-Propoxy






517




CH


3






iso-Propoxy






518




CH


3






n-Butoxy






519




CH


3






iso-Butoxy






520




CH


3






sec.-Butoxy






521




CH


3






tert.-Butoxy






522




CH


3






Methylthio






523




CH


3






Ethylthio






524




CH


3






n-Propylthio






525




CH


3






iso-Propylthio






526




CH


3






n-Butylthio






527




CH


3






iso-Butylthio






528




CH


3






sec.-Butylthio






529




CH


3






tert.-Butylthio






530




CH


3






Benzylthio






531




CH


3






Trifluoromethoxy






532




CH


3






Cyano






533




CH


3






Amino






534




CH


3






Methylamino






535




CH


3






Dimethylamino






536




CH


3






Ethylamino






537




CH


3






Diethylamino






538




CH


3






Di-n-Propylamino






539




CH


3






Di-iso-Propylamino






540




CH


3






Di-n-Butylamino






541




CH


3






Di-iso-Butylamino






542




CH


3






Acetyl






543




CH


3






Propion-1-yl






544




CH


3






Butyr-1-yl






545




CH


3






iso-Butyr-1-yl






546




CH


3






Pivaloyl






547




CH


3






Benzoyl






548




CH


3






4-Chlorobenzoyl






549




CH


3






Benzylcarbonyl






550




CH


3






Methoxycarbonyl






551




CH


3






Ethoxycarbonyl






552




CH


3






n-Propoxycarbonyl






553




CH


3






iso-Propoxycarbonyl






554




CH


3






n-Butoxycarbonyl






555




CH


3






iso-Butoxycarbonyl






556




CH


3






sec.-Butoxycarbonyl






557




CH


3






tert.-Butoxycarbonyl






558




CH


3






n-Hexoxycarbonyl






559




CH


3






Phenoxycarbonyl






560




CH


3






4-Chlorophenoxycarbonyl






561




CH


3






Benzyloxycarbonyl






562




CH


3






Aminocarbonyl






563




CH


3






Dimethylaminocarbonyl






564




CH


3






Diethylaminocarbonyl






565




CH


3






Di-iso-Propylaminocarbonyl






566




CH


3






Phenylaminocarbonyl






567




CH


3






N-Methyl-N-Phenylaminocarbonyl






568




CH


3






Phenyl






569




CH


3






2-Fluorophenyl




m.p.: 89-91° C.; IR (KBr): 1732, 1071, 1012, 998, 768






570




CH


3






3-Fluorophenyl




m.p.: 83-85° C.; IR (KBr): 1724, 1204, 1067, 1031, 1015, 955






571




CH


3






4-Fluorophenyl




m.p.: 76-8° C.;









IR (KBr): 1737, 1510, 1302, 1224, 1072, 1031, 1015, 933






572




CH


3






Pentafluorophenyl






573




CH


3






2-Chlorophenyl






574




CH


3






3-Chlorophenyl




m.p.: 61-63° C.; IR (KBr): 1735, 1070, 1015, 1022, 785






575




CH


3






4-Chlorophenyl




oil; IR (film): 1708, 1634, 1256, 1129






576




CH


3






Pentachlorophenyl






577




CH


3






2,3-Dichlorophenyl






578




CH


3






2,4-Dichlorophenyl






579




CH


3






2,5-Dichlorophenyl






580




CH


3






2,6-Dichlorophenyl






581




CH


3






3,4-Dichlorophenyl






582




CH


3






3,5-Dichlorophenyl




m.p.: 95-7° C.;









IR (KBr): 1723, 1536, 1224, 1067, 1030, 1014, 937






583




CH


3






2,3,4-Trichlorophenyl




m.p.: 110-20° C.;






584




CH


3






2,3,5-Trichlorophenyl






585




CH


3






2,3,6-Trichlorophenyl






586




CH


3






2,4,5-Trichlorophenyl






587




CH


3






2,4,6-Tirchlorophenyl






588




CH


3






3,4,5-Trichlorophenyl






589




CH


3






2,3,4,6-Tetrachlorophenyl






590




CH


3






2,3,5,6-Tetrachlorophenyl






591




CH


3






2-Bromophenyl






592




CH


3






3-Bromophenyl




m.p.: 80-4° C.;









IR (KBr): 1723, 1556, 1224, 1067, 1030, 1014, 957






593




CH


3






4-Bromophenyl




m.p.: 73-75° C.;









IR (KBr): 1736, 1071, 1029, 1015, 932






594




CH


3






2,4-Dibromophenyl






595




CH


3






3-Bromo-4-fluorophenyl






596




CH


3






3-Bromo-4-methoxyphenyl






597




CH


3






2-Iodophenyl






598




CH


3






3-Iodophenyl






599




CH


3






4-Iodophenyl






600




CH


3






2-Chloro-4-fluorophenyl






601




CH


3






2-Chloro-5-fluorophenyl






602




CH


3






2-Chloro-6-fluorophenyl






603




CH


3






2-Chloro-4-bromophenyl






604




CH


3






2-Bromo-4-chlorophenyl






605




CH


3






2-Bromo-4-fluorophenyl






606




CH


3






3-Bromo-4-chlorophenyl






607




CH


3






3-Chloro-4-fluorophenyl






608




CH


3






3-Fluoro-4-chlorophenyl






609




CH


3






2-Cyanophenyl






610




CH


3






3-Cyanophenyl






611




CH


3






4-Cyanophenyl






612




CH


3






2-Nitrophenyl






613




CH


3






3-Nitrophenyl






614




CH


3






4-Nitrophenyl




m.p.: 88-90° C.;









IR (KBr): 1725, 1512, 1342, 1219, 1068, 1009, 854






615




CH


3






2-Methylphenyl






616




CH


3






3-Methylphenyl




m.p.: 93-96° C.;






617




CH


3






4-Methylphenyl




m.p.: 82-84° C.; IR (KBr): 1722, 1068, 1038, 1015, 920






618




CH


3






2,4-Dimethylphenyl






619




CH


3






2,6-Dimethylphenyl






620




CH


3






3,4-Dimethylphenyl






621




CH


3






3,5-Dimethylphenyl






622




CH


3






2,3,4-Trimethylphenyl






623




CH


3






2,3,5-Trimethylphenyl






624




CH


3






2,3,6-Trimethylphenyl






625




CH


3






2,4,5-Trimethylphenyl






626




CH


3






2,4,6-Trimethylphenyl






627




CH


3






3,4,5-Trimethylphenyl






628




CH


3






Pentamethylphenyl






629




CH


3






2-Ethylphenyl






630




CH


3






3-Ethylphenyl






631




CH


3






4-Ethylphenyl






632




CH


3






3,5-Diethylphenyl






633




CH


3






2-n-Propylphenyl






634




CH


3






3-n-Propylphenyl






635




CH


3






4-n-Propylphenyl






636




CH


3






2-iso-Propylphenyl






637




CH


3






3-iso-Propylphenyl






638




CH


3






4-iso-Propylphenyl






639




CH


3






2,4-Di-iso-Propylphenyl






640




CH


3






3,5-Di-iso-Propylphenyl






641




CH


3






4-n-Butylphenyl






642




CH


3






4-sec.-Butylphenyl






643




CH


3






4-iso-Butylphenyl






644




CH


3






4-tert.-Butylphenyl




m.p. 45-50° C.;






645




CH


3






3-tert.-Butylphenyl






646




CH


3






2-tert.-Butylphenyl






647




CH


3






2,4-Di-tert.-Butylphenyl






648




CH


3






3,5-Di-tert.-Butylphenyl






649




CH


3






4-n-Hexylphenyl






650




CH


3






4-n-Dodecylphenyl






651




CH


3






2-Methyl-4-tert.-Butylphenyl






652




CH


3






2-Methyl-6-tert.-Butylphenyl






653




CH


3






2-Methyl-4-iso-Propylphenyl






654




CH


3






2-Methyl-4-Cyclohexylphenyl






655




CH


3






2-Methyl-4-Phenylphenyl






656




CH


3






2-Methyl-4-Benzylphenyl






657




CH


3






2-Methyl-4-Phenoxyphenyl






658




CH


3






2-Methyl-4-Benzyloxyphenyl






659




CH


3






2-Methyl-3-Chlorophenyl






660




CH


3






2-Methyl-4-Chlorophenyl






661




CH


3






2-Methyl-5-Chlorophenyl






662




CH


3






2-Methyl-6-chlorophenyl






663




CH


3






2-Methyl-4-fluorophenyl






664




CH


3






2-Methyl-3-bromophenyl






665




CH


3






2-Methyl-4-bromophenyl






666




CH


3






2-Methyl-3-methoxyphenyl






667




CH


3






2-Methyl-4-methoxyphenyl






668




CH


3






2-Methyl-5-methoxyphenyl






669




CH


3






2-Methyl-6-methoxyphenyl






670




CH


3






2-Methyl-4-iso-Propoxyphenyl






671




CH


3






2-Methyl-2,5-dimethoxyphenyl






672




CH


3






2-Methoxyphenyl




m.p.: 74-6° C.;









IR (KBr): 1741, 1433, 1295, 1249, 1224, 1067, 1022, 878






673




CH


3






3-Methoxyphenyl






674




CH


3






4-Methoxyphenyl




m.p.: 89-91° C.;






675




CH


3






2,3-Dimethoxyphenyl






676




CH


3






2,4-Dimethoxyphenyl






677




CH


3






2,5-Dimethoxyphenyl






678




CH


3






2,6-Dimethoxyphenyl






679




CH


3






3,4-Dimethoxyphenyl






680




CH


3






3,5-Dimethoxyphenyl






681




CH


3






3,6-Dimethoxyphenyl






682




CH


3






2,3,4-Trimethoxyphenyl






683




CH


3






2,3,5-Trimethoxyphenyl






684




CH


3






2,3,6-Trimethoxyphenyl






685




CH


3






2,4,5-Trimethoxyphenyl






686




CH


3






2,4,6-Trimethoxyphenyl






687




CH


3






3,4,5-Trimethoxyphenyl






688




CH


3






2-Ethoxyphenyl






689




CH


3






3-Ethoxyphenyl






690




CH


3






4-Ethoxyphenyl






691




CH


3






2-iso-Propoxyphenyl






692




CH


3






3-iso-propoxyphenyl






693




CH


3






4-iso-propoxyphenyl






694




CH


3






3-tert.-Butoxyphenyl






695




CH


3






4-tert.-Butoxyphenyl






696




CH


3






2-Trifluoromethoxyphenyl






697




CH


3






3-Trifluoromethoxyphenyl






698




CH


3






4-Trifluoromethoxyphenyl






699




CH


3






3-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl






700




CH


3






4-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl






701




CH


3






2-Chloromethylphenyl






702




CH


3






3-Chloromethylphenyl






703




CH


3






4-Chloromethylphenyl






704




CH


3






2-Trifluoromethylphenyl




m.p.: 78-80° C.; IR (KBr): 1741, 1315, 1116, 1068, 1010






705




CH


3






3-Trifluoromethylphenyl




m.p.: 70-72° C.;









IR (KBr): 1740, 1297, 1281, 1164, 1124, 1073, 1010






706




CH


3






4-Trifluoromethylphenyl




m.p.: 57-58° C.; (IR (KBr): 1728, 1333, 1318, 1106, 1069, 986






707




CH


3






2-(Methoxyiminomethyl)phenyl






708




CH


3






3-(Methoxyiminomethyl)phenyl






709




CH


3






4-(Methoxyiminomethyl)phenyl






710




CH


3






2-(Ethoxyiminomethyl)phenyl






711




CH


3






3-(Ethoxyiminomethyl)phenyl






712




CH


3






4-(Ethoxyiminomethyl)phenyl






713




CH


3






2-(n-Propoxyiminomethyl)phenyl






714




CH


3






3-(n-Propoxyiminomethyl)phenyl






715




CH


3






4-(n-Propoxyiminomethyl)phenyl






716




CH


3






2-(iso-Propoxyiminomethyl)phenyl






717




CH


3






3-(iso-Propoxyiminomethyl)phenyl






718




CH


3






4-(iso-Propoxyiminomethyl)phenyl






719




CH


3






2-(n-Butoxyiminomethyl)phenyl






720




CH


3






3-(n-Butoxyiminomethyl)phenyl






721




CH


3






4-(n-Butoxyiminomethyl)phenyl






722




CH


3






2-(iso-Butoxyiminomethyl)phenyl






723




CH


3






3-(iso-Butoxyiminomethyl)phenyl






724




CH


3






4-(iso-Butoxyiminomethyl)phenyl






725




CH


3






2-(tert.-Butoxyiminomethyl)phenyl






726




CH


3






3-(tert.-Butoxyiminomethyl)phenyl






727




CH


3






4-(tert.-Butoxyiminomethyl)phenyl






728




CH


3






2-(n-Pentoxyiminomethyl)phenyl






729




CH


3






3-(n-Pentoxyiminomethyl)phenyl






730




CH


3






4-(n-Pentoxyiminomethyl)phenyl






731




CH


3






2-(n-Hexoxyiminomethyl)phenyl






732




CH


3






3-(n-Hexoxyiminomethyl)phenyl






733




CH


3






4-(n-Hexoxyiminomethyl)phenyl






734




CH


3






2-(Allyloxyiminomethyl)phenyl






735




CH


3






3-(Allyloxyiminomethyl)phenyl






736




CH


3






4-(Allyloxyiminomethyl)phenyl






737




CH


3






2-(Benzyloxyiminomethyl)phenyl






738




CH


3






3-(Benzyloxyiminomethyl)phenyl






739




CH


3






4-(Benzyloxyiminomethyl)phenyl






740




CH


3






2-(Methoxyimino-1′-ethyl)phenyl






741




CH


3






3-(Methoxyimino-1′-ethyl)phenyl






742




CH


3






4-(Methoxyimino-1′-ethyl)phenyl






743




CH


3






2-(Ethoxyimino-1′-ethyl)phenyl






744




CH


3






3-(Ethoxyimino-1′-ethyl)phenyl






745




CH


3






4-(Ethoxyimino-1′-ethyl)phenyl






746




CH


3






2-(n-Propoxyimino-1′-ethyl)phenyl






747




CH


3






3-(n-Propoxyimino-1′-ethyl)phenyl






748




CH


3






4-(n-Propoxyimino-1′-ethyl)phenyl






749




CH


3






2-(n-Butoxyamino-1′-ethyl)phenyl






750




CH


3






3-(n-Butoxyamino-1′-ethyl)phenyl






751




CH


3






4-(n-Butoxyamino-1′-ethyl)phenyl






752




CH


3






2-(n-Pentoxyimino-1′-ethyl)phenyl






753




CH


3






3-(n-Pentoxyimino-1′-ethyl)phenyl






754




CH


3






4-(n-Pentoxyimino-1′-ethly)phenyl






755




CH


3






2-(n-Hexoxyimino-1′-ethyl)phenyl






756




CH


3






3-(n-Hexoxyimino-1′-ethyl)phenyl






757




CH


3






4-(n-Hexoxyimino-1′-ethyl)phenyl






758




CH


3






2-(Allyloxyimino-1′-ethyl)phenyl






759




CH


3






3-(Allyloxyimino-1′-ethyl)phenyl






760




CH


3






4-(Allyloxyimino-1′-ethyl)phenyl






761




CH


3






2-(Benzyloxyimino-1′-ethyl)phenyl






762




CH


3






3-(Benzyloxyimino-1′-ethyl)phenyl






763




CH


3






4-(Benzyloxyimino-1′-ethyl)phenyl






764




CH


3






2-Phenylphenyl






765




CH


3






3-Phenylphenyl






766




CH


3






4-Phenylphenyl






767




CH


3






2-Phenoxyphenyl






768




CH


3






3-Phenoxyphenyl






769




CH


3






4-Phenoxyphenyl




m.p.: 91-3° C.;









IR (KBr): 1732, 1587, 1491, 1241, 1071, 1014, 995, 769






770




CH


3






2-Benzyloxyphenyl






771




CH


3






3-Benzyloxyphenyl






772




CH


3






4-Benzyloxyphenyl






773




CH


3






4-(Imidazol-1′-yl)phenyl






774




CH


3






4-(Piperazin-1′-yl)phenyl






775




CH


3






4-(Morpholin-1′-yl)phenyl






776




CH


3






4-(Piperadin-1′-yl)phenyl






777




CH


3






4-(Pyridyl-2′-oxy)phenyl






778




CH


3






2-Cyclopropylphenyl






779




CH


3






3-Cyclopropylphenyl






780




CH


3






4-Cyclopropylphenyl






781




CH


3






3-Cyclohexylphenyl






782




CH


3






4-Cyclohexylphenyl




m.p.: 53-5° C.;






783




CH


3






4-Oxiramylphenyl






784




CH


3






4-(1′,3′-Dioxan-2′-yl)phenyl






785




CH


3






4-(Tetrahydropyro-2-yloxy)phenyl






786




CH


3






1-Naphthyl






787




CH


3






2-Naphthyl






788




CH


3






9-Anthryl






789




CH


3






1-Naphthoxy






790




CH


3






2-Naphthoxy






791




CH


3






9-Anthroxy






792




CH


3






Phenoxy






793




CH


3






2-Chlorophenoxy






794




CH


3






3-Chlorophenoxy






795




CH


3






4-Chlorophenoxy






796




CH


3






4-Methylphenoxy






797




CH


3






4-tert.-Butylphenoxy






798




CH


3






4-Methoxyphenoxy






799




CH


3






4-Ethoxyphenoxy






800




CH


3






4-tert.-Butoxyphenoxy






801




CH


3






Phenylthio






802




CH


3






2-Chlorophenylthio






803




CH


3






4-Chlorophenylthio






804




CH


3






Benzyl






805




CH


3






2-Methylbenzyl






806




CH


3






3-Methylbenzyl






807




CH


3






4-Methylbenzyl






808




CH


3






4-tert.-Butylbenzyl






809




CH


3






2-Chlorobenzyl






810




CH


3






3-Chlorobenzyl






811




CH


3






4-Chlorobenzyl






812




CH


3






2,4-Dichlorobenzyl






813




CH


3






2,6-Dichlorobenzyl






814




CH


3






2,4,6-Trichlorobenzyl






815




CH


3






2-Trifluoromethylbenzyl






816




CH


3






3-Trifluoromethylbenzyl






817




CH


3






4-Trifluoromethylbenzyl






818




CH


3






2-Methoxybenzyl






819




CH


3






4-Methoxybenzyl






820




CH


3






4-tert.-Butoxybenzyl






821




CH


3






4-Phenoxybenzyl






822




CH


3






1-Phenethyl






823




CH


3






2-Phenethyl






824




CH


3






1-Phenylpropyl






825




CH


3






2-Phenylpropyl






826




CH


3






3-Phenylpropyl






827




CH


3






2-Methyl-2-phenylpropyl






828




CH


3






2-Methyl-3-phenylpropyl






829




CH


3






4-Phenylbutyl






830




CH


3






2-Phenyl-1-ethenyl






831




CH


3






1-Phenyl-1-ethenyl






832




CH


3






1-Phenyl-1-propenyl






833




CH


3






1-Phenyl-1-propen-2-yl






834




CH


3






2,2-Diphenylethenyl






835




CH


3






Phenoxymethyl






836




CH


3






2-Pyridyl






837




CH


3






3-Pyridyl






838




CH


3






4-Pyridyl






839




CH


3






2,6-Pyrimidinyl






840




CH


3






1,5-Pyrimidinyl






841




CH


3






2-Thienyl






842




CH


3






3-Thienyl






843




CH


3






2-Furyl






844




CH


3






3-Furyl






845




CH


3






1-Pyrrolyl






846




CH


3






1-Imidazolyl






847




CH


3






1,2,4-Triazolyl






848




CH


3






1,3,4-Triazolyl






849




CH


3






4-Thiazolyl






850




CH


3






2-Benzothiazolyl






851




CH


3






2-Pyridyloxy






852




CH


3






2-Pyrimidiayloxy






853




CH


3






2-Pyridylthio






854




CH


3






2-Pyrimidinylthio






855




CH


3






2-Benzothiazolythio






856




CH


3






Phenylthiomethyl






857




CH


3






2-Pyridylmethyl






858




CH


3






3-Pyridylmethyl






859




CH


3






Furfuryloxy






860




CH


3






Thienylmethoxy






861




CH


3






3-Isoxazolylmethoxy






862




CH


3






2-Oxoxazolymethoxy






863




CH


3






2-Pyridylmethoxy






864




CH


3






2′-Furyl-2-ethenyl






865




CH


3






2′-Thienyl-2-ethenyl






866




CH


3






3′-Pyridyl-2-ethenyl






867




CH


3






Oxinanyl






868




CH


3






1-Azinidinyl






869




CH


3






1-Azinidinyl






870




CH


3






1-Pyrrolidinyl






871




CH


3






2-Tetrahydrofuryl






872




CH


3






2-Tetrahydropyranyl






873




CH


3






3-Tetrahydropyranyl






874




CH


3






1-Piperdinyl






875




CH


3






1-Morpholinyl






876




CH


3






1-Piperezinyl






877




CH


3






1,3-Dioxan-2-yl






878




CH


3






3-Tetrahydrothiopyranyl






879




CH


3






2-Dihydropyranyloxy






880




CH


3






2-Tetrahydropyranyloxy






881




CH


3






CF


3








882




CH


3






2-Fluoroethyl






883




CH


3






2,2,2-Trifluoroethyl






884




CH


3






Pentafluoroethyl






885




CH


3






Chloromethyl






886




CH


3






Dichloromethyl






887




CH


3






Trichloromethyl






888




CH


3






2-Chloroethyl






889




CH


3






2,2,2-Trichloromethyl






890




CH


3






Pentachloroethyl






891




CH


3






Cyclopropyl






892




CH


3






Cyclobutyl






893




CH


3






Cyclopentyl






894




CH


3






Cyclohexyl






895




CH


3






1-Methylcyclopropyl






896




CH


3






2,2-Dimethylcyclopropyl






897




CH


3






1-Methylcyclohexyl






898




CH


3






2,2-Difluorocyclopropyl






899




CH


3






2,2-Dichlorocyclopropyl






900




CH


3






2,2-Dibromocyclopropyl






901




CH


3






2,2-Dichloro-3-Methylcyclopropyl






902




CH


3






2,2,3,3-Tetrafluorocyclobutyl






903




CH


3






Ethenyl






904




CH


3






1-Propenyl






905




CH


3






2-Methyl-1-propenyl






906




CH


3






4-Methylpent-3-en-1-yl






907




CH


3






2-Propenyl






908




CH


3






2-Bucanyl






909




CH


3






1-Methyl-2-propenyl






910




CH


3






3-Methyl-2-butenyl






911




CH


3






2,2-Difluoroethenyl






912




CH


3






2,2-Dichloroethenyl






913




CH


3






3,3,3-Trifluoropropenyl






914




CH


3






3,3,3-Trichloropropenyl






915




CH


3






3-Chloro-2-propenyl






916




CH


3






Cyclopent-1-enyl






917




CH


3






Cyclopentadienyl






918




CH


3






Cyclohex-1-enyl






919




CH


3






Pentafluorocyclopentadienyl






920




CH


3






Pentachlorocyclopentadienyl






921




Phenyl




Phenyl






922




Phenyl




2-Fluorophenyl






923




Phenyl




4-Fluorophenyl






924




Phenyl




2-Chlorophenyl






925




Phenyl




3-Chlorophenyl






926




Phenyl




4-Chlorophenyl






927




Phenyl




3,4-Dichlorophenyl






928




Phenyl




4-Nitrophenyl






929




Phenyl




2-CF


3


-Phenyl






930




Phenyl




3-CF


3


-Phenyl






931




Phenyl




4-CF


3


-Phenyl






932




Phenyl




2-Methylphenyl






933




Phenyl




3-Methylphenyl






934




Phenyl




4-Methylphenyl






935




Phenyl




2,4-Dimethylphenyl






936




Phenyl




4-tert.-Butylphenyl






937




Phenyl




4-Methoxyphenyl






938




4-Fluorophenyl




4-Fluorophenyl






939




2-Fluorophenyl




4-Fluorophenyl






940




2-Chlorophenyl




4-Fluorophenyl






941




2-Chlorophenyl




2-Chlorophenyl






942




3-Chlorophenyl




3-Chlorophenyl






943




4-Chlorophenyl




4-Chlorophenyl






944




2-Chlorophenyl




4-Chlorophenyl






945




4-Methoxyphenyl




4-Methoxyphenyl






946




4-Dimethylaminophenyl




4-Dimethylaminophenyl






947




Phenyl




Naphethyl






948




Ethyl




Ethyl






949




Ethyl




n-Propyl






950




Ethyl




iso-Propyl






951




Ethyl




n-Butyl






952




Ethyl




iso-Butyl






953




Ethyl




2-Methyl-butyl






954




Ethyl




Benzyl






955




n-Propyl




n-Propyl






956




iso-Propyl




iso-Propyl






957




n-Butyl




n-Butyl






958




iso-Butyl




iso-Butyl






959




tert.-Butyl




tert.-Butyl






960




Benzyl




Benzyl






961




Pentachloroethyl




Pentachloroethyl






962




n-Hexyl




n-Hexyl






963




Ethoxycarbonyl




Ethoxycarbonyl






964




Phenyl




Benzoyl






965




Ethyl




Phenyl






966




N-Butyl




Phenyl






967




Styryl




Styryl






968




2-Pyridyl




2-Pyridyl






969




3-Pyridyl




3-Pyridyl






970




Ethyl




2-Pyridyl




m.p.: 84-86° C.;




















971
















m.p.: 103-105° C.;






















TABLE III















































No.




X




Y




R


1






R


2


= H




R


3






R


4






Data









1




CHS—CH


3






O




CH


3







CF


3






Phenyl






2




CHS—CH


3






O




CH


3







Cyclopropyl




Phenyl






3




CHS—CH


3






O




CH


3







Cyclopropyl




4-Chlorophenyl






4




CHS—CH


3






O




CH


3







Cyclopropyl




4-Methoxyphenyl






5




CHS—CH


3






O




CH


3







Cyclopropyl




4-tert.-butylphenyl






6




CHS—CH


3






O




CH


3







CN




Methylthio






7




CHS—CH


3






O




CH


3







CN




2-Methoxyprop-2-yl






8




CHS—CH


3






O




CH


3







CN




2-Methylthioprop-2-yl






9




CHS—CH


3






O




CH


3







CN




Phenylthio






10




CHS—CH


3






O




CH


3







CN




iso-Propyl






11




CHS—CH


3






O




CH


3







CN




CN






12




CHS—CH


3






O




CH


3







CN




Acetyl






13




CHS—CH


3






O




CH


3







CN




Benzoyl






14




CHS—CH


3






O




CH


3







CN




Methoxycarbonyl






15




CHS—CH


3






O




CH


3







CN




Phenyl






16




CHS—CH


3






O




CH


3







CN




2-Chlorophenyl






17




CHS—CH


3






O




CH


3







CN




4-Chlorophenyl






18




CHS—CH


3






O




CH


3







CN




2-Methylphenyl






19




CHS—CH


3






O




CH


3







CN




4-tert.-butylphenyl






20




CHS—CH


3






O




CH


3







CN




4-n-Butoxyiminomethyl)phenyl






21




CHS—CH


3






O




CH


3







CN




2-Pyridyl






22




CHS—CH


3






O




CH


3







CN




Styryl






23




CHS—CH


3






O




CH


3







CN




1-Propenyl






24




CHS—CH


3






O




CH


3







CH


3






Phenylthio






25




CHS—CH


3






O




CH


3







CH


3






Benzyl






26




CHS—CH


3






O




CH


3







CH


3






tert.-Butyl






27




CHS—CH


3






O




CH


3







CH


3






iso-Propyl






28




CHS—CH


3






O




CH


3







CH


3






2-Methylbutyl






29




CHS—CH


3






O




CH


3







CH


3






iso-Butyl






30




CHS—CH


3






O




CH


3







CH


3






Phenyl






31




CHS—CH


3






O




CH


3







CH


3






2-Chlorophenyl






32




CHS—CH


3






O




CH


3







CH


3






4-Chlorophenyl






33




CHS—CH


3






O




CH


3







CH


3






2-Methylphenyl






34




CHS—CH


3






O




CH


3







CH


3






Naphthyl






35




CHS—CH


3






O




CH


3







CH


3






1-Pyridyl






36




CHS—CH


3






O




CH


3







iso-Butyl




iso-Butyl






37




CHS—CH


3






O




CH


3







Phenyl




Phenyl






38




CHS—CH


3






O




CH


3








CH


2


CH


2


CH


2


CH


2



















39




CHS—CH


3






O




CH


3







CH


2


CH


2


CH


2


CH


2


CH


2





















40




CH—CH


3






O




CH


3







CF


3






Phenyl







41




CH—CH


3






O




CH


3







Cyclopropyl




Phenyl






42




CH—CH


3






O




CH


3







Cyclopropyl




4-Chlorophenyl






43




CH—CH


3






O




CH


3







Cyclopropyl




4-Methoxyphenyl






44




CH—CH


3






O




CH


3







Cyclopropyl




4-tert.-butylphenyl






45




CH—CH


3






O




CH


3







CN




Methylthio






46




CH—CH


3






O




CH


3







CN




2-Methoxyprop-2-yl




IR (film): 1717, 1436, 1367, 1256,













1210, 1179, 1070, 1037, 1009, 759






47




CH—CH


3






O




CH


3







CN




2-Methylthioprop-2-yl






1


H-NMR (CDCl


3


): δ = 1.45s, 1.6d,













1.8s, 3.7s, 5.1s, 7.1-7.5m






48




CH—CH


3






O




CH


3







CN




Phenylthio






49




CH—CH


3






O




CH


3







CN




iso-Propyl






1


H-NMR (CDCl


3


): δ = 1.2d, 1.6d,













2.7m, 3.67s, 5.1s, 7.0-7.5m






50




CH—CH


3






O




CH


3







CN




CN






51




CH—CH


3






O




CH


3







CN




Acetyl






52




CH—CH


3






O




CH


3







CN




Benzoyl






53




CH—CH


3






O




CH


3







CN




Methoxycarbonyl






54




CH—CH


3






O




CH


3







CN




Phenyl






1


H-NMR (CDCl


3


): δ = 1.6d, 3.7s,













5.2s, 7.0-1.8m






55




CH—CH


3






O




CH


3







CN




2-Chlorophenyl






56




CH—CH


3






O




CH


3







CN




4-Chlorophenyl






57




CH—CH


3






O




CH


3







CN




2-Methylphenyl






58




CH—CH


3






O




CH


3







CN




4-tert.-butylphenyl






59




CH—CH


3






O




CH


3







CN




4-(n-Butoxyiminomethyl)phenyl






60




CH—CH


3






O




CH


3







CN




2-Pyridyl






61




CH—CH


3






O




CH


3







CN




Styryl






62




CH—CH


3






O




CH


3







CN




1-Propenyl






63




CH—CH


3






O




CH


3







CH


3






Phenylthio






64




CH—CH


3






O




CH


3







CH


3






Benzyl






65




CH—CH


3






O




CH


3







CH


3






tert.-Butyl






66




CH—CH


3






O




CH


3







CH


3






iso-Propyl






67




CH—CH


3






O




CH


3







CH


3






2-Methylbutyl






68




CH—CH


3






O




CH


3







CH


3






iso-Butyl






69




CH—CH


3






O




CH


3







CH


3






Phenyl






70




CH—CH


3






O




CH


3







CH


3






2-Chlorophenyl






71




CH—CH


3






O




CH


3







CH


3






4-Chlorophenyl




IR (film): 1716, 1490, 1434, 1253,













1206, 1096, 1036, 1012, 820, 760






72




CH—CH


3






O




CH


3







CH


3






2-Methylphenyl






73




CH—CH


3






O




CH


3







CH


3






Naphthyl






74




CH—CH


3






O




CH


3







CH


3






1-Pyridyl






75




CH—CH


3






O




CH


3







iso-Butyl




iso-Butyl






76




CH—CH


3






O




CH


3







Phenyl




Phenyl






77




CH—CH


3






O




CH


3








CH


2


CH


2


CH


2


CH


2



















78




CH—CH


3






O




CH


3







CH


2


CH


2


CH


2


CH


2


CH


2





















79




CH


2






O




CH


3







CF


3






Phenyl







80




CH


2






O




CH


3







Cyclopropyl




Phenyl






81




CH


2






O




CH


3







Cyclopropyl




4-Chlorophenyl






82




CH


2






O




CH


3







Cyclopropyl




4-Methoxyphenyl






83




CH


2






O




CH


3







Cyclopropyl




4-tert.-butylphenyl






84




CH


2






O




CH


3







CN




Methylthio






85




CH


2






O




CH


3







CN




2-Methoxyprop-2-yl






86




CH


2






O




CH


3







CN




2-Methylthioprop-2-yl






87




CH


2






O




CH


3







CN




Phenylthio






88




CH


2






O




CH


3







CN




iso-Propyl






89




CH


2






O




CH


3







CN




CN






90




CH


2






O




CH


3







CN




Acetyl






91




CH


2






O




CH


3







CN




Benzoyl






92




CH


2






O




CH


3







CN




Methoxycarbonyl






93




CH


2






O




CH


3







CN




Phenyl






94




CH


2






O




CH


3







CN




2-Chlorophenyl






95




CH


2






O




CH


3







CN




4-Chlorophenyl






96




CH


2






O




CH


3







CN




2-Methylphenyl






97




CH


2






O




CH


3







CN




4-tert.-butylphenyl






98




CH


2






O




CH


3







CN




4-(n-Butoxyiminomethyl)phenyl






99




CH


2






O




CH


3







CN




2-Pyridyl






100




CH


2






O




CH


3







CN




Styryl






101




CH


2






O




CH


3







CN




1-Propenyl






102




CH


2






O




CH


3







CH


3






Phenylthio






103




CH


2






O




CH


3







CH


3






Benzyl






104




CH


2






O




CH


3







CH


3






tert.-Butyl






105




CH


2






O




CH


3







CH


3






iso-Propyl






106




CH


2






O




CH


3







CH


3






2-Methylbutyl






107




CH


2






O




CH


3







CH


3






iso-Butyl






108




CH


2






O




CH


3







CH


3






Phenyl






109




CH


2






O




CH


3







CH


3






2-Chlorophenyl






110




CH


2






O




CH


3







CH


3






4-Chlorophenyl






111




CH


2






O




CH


3







CH


3






2-Methylphenyl






112




CH


2






O




CH


3







CH


3






Naphthyl






113




CH


2






O




CH


3







CH


3






1-Pyridyl






114




CH


2






O




CH


3







iso-Butyl




iso-Butyl






115




CH


2






O




CH


3







Phenyl




Phenyl






116




CH


2






O




CH


3








CH


2


CH


2


CH


2


CH


2



















117




CH


2






O




CH


3







CH


2


CH


2


CH


2


CH


2


CH


2





















118




N—OCH


3






S




CH


3







CF


3






Phenyl







119




N—OCH


3






S




CH


3







Cyclopropyl




Phenyl






120




N—OCH


3






S




CH


3







Cyclopropyl




4-Chlorophenyl






121




N—OCH


3






S




CH


3







Cyclopropyl




4-Methoxyphenyl






122




N—OCH


3






S




CH


3







Cycloproyl




4-tert.-butylphenyl






123




N—OCH


3






S




CH


3







CN




Methylthio






124




N—OCH


3






S




CH


3







CN




2-Methoxyprop-2-yl






125




N—OCH


3






S




CH


3







CN




2-Methylthioprop-2-yl






126




N—OCH


3






S




CH


3







CN




Phenylthio






127




N—OCH


3






S




CH


3







CN




iso-Propyl






128




N—OCH


3






S




CH


3







CN




CN






129




N—OCH


3






S




CH


3







CN




Acetyl






130




N—OCH


3






S




CH


3







CN




Benzoyl






131




N—OCH


3






S




CH


3







CN




Methoxycarbonyl






132




N—OCH


3






S




CH


3







CN




Phenyl






133




N—OCH


3






S




CH


3







CN




2-Chlorophenyl






134




N—OCH


3






S




CH


3







CN




4-Chlorophenyl






135




N—OCH


3






S




CH


3







CN




2-Methylphenyl






136




N—OCH


3






S




CH


3







CN




4-tert.-butylphenyl






137




N—OCH


3






S




CH


3







CN




4-(n-Butoxyiminomethyl)phenyl






138




N—OCH


3






S




CH


3







CN




2-Pyridyl






139




N—OCH


3






S




CH


3







CN




Styryl






140




N—OCH


3






S




CH


3







CN




1-Propenyl






141




N—OCH


3






S




CH


3







CH


3






Phenylthio






142




N—OCH


3






S




CH


3







CH


3






Benzyl






143




N—OCH


3






S




CH


3







CH


3






tert.-Butyl






144




N—OCH


3






S




CH


3







CH


3






iso-Propyl






145




N—OCH


3






S




CH


3







CH


3






2-Methylbutyl






146




N—OCH


3






S




CH


3







CH


3






iso-Butyl






147




N—OCH


3






S




CH


3







CH


3






Phenyl






148




N—OCH


3






S




CH


3







CH


3






2-Chlorophenyl






149




N—OCH


3






S




CH


3







CH


3






4-Chlorophenyl






150




N—OCH


3






S




CH


3







CH


3






2-Methylphenyl






151




N—OCH


3






S




CH


3







CH


3






Naphthyl






152




N—OCH


3






S




CH


3







CH


3






1-Pyridyl






153




N—OCH


3






S




CH


3







iso-butyl




iso-Butyl






154




N—OCH


3






S




CH


3







Phenyl




Phenyl






155




N—OCH


3






S




CH


3








CH


2


CH


2


CH


2


CH


2



















156




N—OCH


3






S




CH


3







CH


2


CH


2


CH


2


CH


2


CH


2





















157




N—OCH


3






NH




CH


3







CF


3






Phenyl







158




N—OCH


3






NH




CH


3







Cyclopropyl




Phenyl






159




N—OCH


3






NH




CH


3







Cyclopropyl




4-Chlorophenyl




m.p.: 71-74° C.













IR (KBr): 3348, 1663, 1529, 1042,













1030, 982






160




N—OCH


3






NH




CH


3







Cyclopropyl




4-Methoxyphenyl






161




N—OCH


3






NH




CH


3







Cyclopropyl




4-tert.-butylphenyl






162




N—OCH


3






NH




CH


3







CN




Methylthio






163




N—OCH


3






NH




CH


3







CN




2-Methoxyprop-2-yl






164




N—OCH


3






NH




CH


3







CN




2-Methylthioprop-2-yl






165




N—OCH


3






NH




CH


3







CN




Phenylthio






166




N—OCH


3






NH




CH


3







CN




iso-Propyl






167




N—OCH


3






NH




CH


3







CN




CN






168




N—OCH


3






NH




CH


3







CN




Acetyl






169




N—OCH


3






NH




CH


3







CN




Benzoyl






170




N—OCH


3






NH




CH


3







CN




Methoxycarbonyl






171




N—OCH


3






NH




CH


3







CN




Phenyl






172




N—OCH


3






NH




CH


3







CN




2-Chlorophenyl






173




N—OCH


3






NH




CH


3







CN




4-Chlorophenyl






174




N—OCH


3






NH




CH


3







CN




2-Methylphenyl






175




N—OCH


3






NH




CH


3







CN




4-tert.-butylphenyl






176




N—OCH


3






NH




CH


3







CN




4-(n-Butoxyiminomethyl)phenyl






177




N—OCH


3






NH




CH


3







CN




2-Pyridyl






178




N—OCH


3






NH




CH


3







CN




Styryl






179




N—OCH


3






NH




CH


3







CN




1-Propenyl






180




N—OCH


3






NH




CH


3







CH


3






Phenylthio






181




N—OCH


3






NH




CH


3







CH


3






Benzyl






182




N—OCH


3






NH




CH


3







CH


3






tert.-Butyl






183




N—OCH


3






NH




CH


3







CH


3






iso-Propyl






184




N—OCH


3






NH




CH


3







CH


3






2-Methylbutyl






185




N—OCH


3






NH




CH


3







CH


3






iso-Butyl






186




N—OCH


3






NH




CH


3







CH


3






Phenyl






187




N—OCH


3






NH




CH


3







CH


3






2-Chlorophenyl






188




N—OCH


3






NH




CH


3







CH


3






4-Chlorophenyl




m.p.: 119-121° C.













IR (KBr): 3421, 1676, 1037, 985,













933, 752






189




N—OCH


3






NH




CH


3







CH


3






2-Methylphenyl









No.




X




Y




R


1






R


2






R


3






R


4






Data









190




N—OCH


3






NH




CH


3






H




CH


3






Naphthyl






191




N—OCH


3






NH




CH


3






H




CH


3






1-Pyridyl






192




N—OCH


3






NH




CH


3






H




iso-Butyl




iso-Butyl






193




N—OCH


3






NH




CH


3






H




Phenyl




Phenyl






194




N—OCH


3






NH




CH


3






H





CH


2


CH


2


CH


2


CH


2



















195




N—OCH


3






NH




CH


3






H




CH


2


CH


2


CH


2


CH


2


CH


2





















196




N—OCH


3






O




C


2


H


5






H




CH


3






Phenyl







197




CH—OCH


3






O




C


2


H


5






H




CH


3






Phenyl






198




N—OCH


3






O




n-C


3


H


5






H




CH


3






Phenyl






199




CHOCH


3






O




n-C


3


H


5






H




CH


3






Phenyl






200




CHC


2


H


5






O




CH


3






H




CH


3






Phenyl






201




N—OCH


3






O




CH


3






CH


3






CH


3






Phenyl






202




CHOCH


3






O




CH


3






CH


3






CH


3






Phenyl






203




N—OCH


3






O




CH


3






CH


3






CN




Phenyl






204




CHOCH


3






O




CH


3






CH


3






CN




Phenyl






205




CHS—CH


3






O




CH


3






H




H




Phenyl






206




CH—CH


3






O




CH


3






H




H




Phenyl






207




CH


2






O




CH


3






H




H




Phenyl






208




NOCH


3






S




CH


3






H




H




Phenyl






209




CHOCH


3






S




CH


3






H




H




Phenyl






210




CHOCH


3






NH




CH


3






H




H




Phenyl






211




NOCH


3






NH




CH


3






H




H




Phenyl






212




CH—OCH


3






S




CH


3






H




CN




Methylthio









No.




X




Y




R


1






R


2


= H




R


3






R


4






Data









213




CH—OCH


3






S




CH


3







CN




2-Methoxyprop-2-yl






214




CH—OCH


3






S




CH


3







CN




2-Methylthioprop-2-yl






215




CH—OCH


3






S




CH


3







CN




Phenylthio






216




CH—OCH


3






S




CH


3







CN




iso-Propyl






217




CH—OCH


3






S




CH


3







CN




CN






218




CH—OCH


3






S




CH


3







CN




Acetyl






219




CH—OCH


3






S




CH


3







CN




Benzoyl






220




CH—OCH


3






S




CH


3







CN




Methoxycarbonyl






221




CH—OCH


3






S




CH


3







CN




Phenyl






222




CH—OCH


3






S




CH


3







CN




2-Chlorophenyl






223




CH—OCH


3






S




CH


3







CN




4-Chlorophenyl






224




CH—OCH


3






S




CH


3







CN




2-Methylphenyl






225




CH—OCH


3






S




CH


3







CN




4-tert.-butylphenyl






226




CH—OCH


3






S




CH


3







CN




4-(n-Butoxyiminomethyl)phenyl






227




CH—OCH


3






S




CH


3







CN




2-Pyridyl






228




CH—OCH


3






S




CH


3







CN




Styryl






229




CH—OCH


3






S




CH


3







CN




1-Propenyl






230




CH—OCH


3






S




CH


3







CN




Methylthio






231




CH—OCH


3






NH




CH


3







CN




2-Methoxyprop-2-yl






232




CH—OCH


3






NH




CH


3







CN




2-Methylthioprop-2-yl






233




CH—OCH


3






NH




CH


3







CN




Phenylthio






234




CH—OCH


3






NH




CH


3







CN




iso-Propyl






235




CH—OCH


3






NH




CH


3







CN




CN






236




CH—OCH


3






NH




CH


3







CN




Acetyl






237




CH—OCH


3






NH




CH


3







CN




Benzoyl






238




CH—OCH


3






NH




CH


3







CN




Methoxycarbonyl






239




CH—OCH


3






NH




CH


3







CN




Phenyl






240




CH—OCH


3






NH




CH


3







CN




2-Chlorophenyl






241




CH—OCH


3






NH




CH


3







CN




4-Chlorophenyl






242




CH—OCH


3






NH




CH


3







CN




2-Methylphenyl






243




CH—OCH


3






NH




CH


3







CN




4-tert.-butylphenyl






244




CH—OCH


3






NH




CH


3







CN




4-(n-Butoxyiminomethyl)phenyl






245




CH—OCH


3






NH




CH


3







CN




2-Pyridyl






246




CH—OCH


3






NH




CH


3







CN




Styryl






247




CH—OCH


3






NH




CH


3







CN




1-Propenyl






248




N—OCH


3






NH




CH


3







CH


3






3-Chlorophenyl




m.p.: 71-74° C.






249




N—OCH


3






NH




CH


3







CH


3






3,5-Dichlorophenyl




m.p.: 94-97° C.






250




N—OCH


3






NH




CH


3







CH


3






2,3,4-Trichlorophenyl




m.p.: 110-112° C.






251




N—OCH


3






NH




CH


3







CH


3






3-Bromophenyl




m.p.: 74-77° C.






252




N—OCH


3






NH




CH


3







CH


3






4-Methylphenyl




m.p.: 69-72° C.






253




N—OCH


3






NH




CH


3







CH


3






4-Nitrophenyl




m.p.: 134-137° C.






254




CH—CH


3






O




CH


3







CN




2-Ethoxy-prop-2-yl




IR (film): 2982, 1717, 1436, 1255, 1210,













1192, 1067, 1037, 1010






255




CH—CH


3






O




CH


3







CN




2-i-Propoxy-prop-2-yl




IR (film): 2983, 1718, 1383, 1370, 1255,













1173, 1119, 1109, 1037, 1002






256




CH—CH


3






O




CH


3







CN




2-n-Butyoxy-prop-2-yl




IR (film): 2957, 1718, 1435, 1255, 1176,













1036, 1010, 759






257




CH—CH


3






O




CH


3







CN




2-i-Butyoxy-prop-2-yl




IR (film): 2956, 1717, 1435, 1366, 1255,













1209, 1176, 1064, 1037, 1008






258




CH—CH


3






O




CH


3







CN




Cyclopropyl






1


H-NMR (CDCl


3


): δ = 0.9m, 1.6d,













2.3m, 3.67s, 5.15s, 7.05-7.4m






259




CH—CH


3






O




CH


3







CN




2-Ethylthio-prop-2-yl






1


H-NMR (CDCl


3


): δ = 1.1t, 1,5s,













1.6d, 2.2q, 3.7s, 5.1s, 7.1-7.5m






260




CH—CH


3






O




CH


3







CN




2-i-Propylthio-pro-2-yl






1


H-NMR (CDCl


3


): δ = 1.15s, 1.5s,













1.6d, 2.6m, 3.7s, 5.1s, 7.1-7.5m






261




CH—CH


3






O




CH


3







CN




2-Tetrahydropyranyl






1


H-NMR (CDCl


3


): δ = 1.4-1.9m,













1.6d, 3.5m, 3.7s, 4.1m, 5.1s,













7.0-7.5m






















TABLE IV











































No.




X




Y




R


1






R


3






R


4






Data




















1




CH—OCH


3






O




CH


3






CH


3






Phenyl







2




CH—OCH


3






O




CH


3






CH


3






3-Bromophenyl






3




CH—OCH


3






O




CH


3






CH


3






4-Phenoxyphenyl






4




CH—OCH


3






O




CH


3






CH


3






4-Cyclohexylphenyl






5




NOCH


3






O




CH


3






CH


3






Phenyl






6




NOCH


3






O




CH


3






CH


3






3-Bromophenyl




oil: IR (film): 1727, 1436, 1312, 1240, 1032






7




NOCH


3






O




CH


3






CH


3






4-Phenoxyphenyl




oil: IR (film): 1727, 1489, 1239, 1031, 683






8




NOCH


3






O




CH


3






CH


3






4-Cyclohexylphenyl




oil: IR (film): 2925, 1728, 1447, 1239, 1164, 1077, 1032






9




CHOCH


3






O




CH


3






CN




iso-Propyl




2970, 2220, 1710, 1127






10




CHOCH


3






O




CH


3






CN




2-Methoxyprop-2-yl




oil: IR (film): 2980, 2220, 1710, 1127






11




CHOCH


3






O




CH


3






CN




2-Methylthioprop-2-yl




oil: IR (film): 2980, 2220, 1709, 1127






12




CHOCH


3






O




CH


3






CN




2-Tetrahydrofuranyl




oil: IR (film): 2945, 2850, 2220, 1709, 1127






13




CHOCH


3






O




CH


3






CN




Phenyl




oil: IR (film): 2940, 2220, 1709, 1127, 1030






















TABLE V








































No.




R


3






R


4






Data

















1




H




H







2




H




Methoxymethyl






3




H




Ethoxymethyl






4




H




n-Propoxymethyl






5




H




iso-Propoxymethyl






6




H




tert.-Butoxymethyl






7




H




2-Methoxyprop-2-yl






8




H




2-Ethoxyprop-2-yl






9




H




2-n-Propoxyprop-2-yl






10




H




2-iso-Propoxyprop-2-yl






11




H




2-tert.-Butoxyprop-2-yl






12




H




Methylthiomethyl






13




H




tert.-Butylthioprop-2-yl






14




H




2-Methylthioprop-2-yl






15




H




2-iso-Propylthioprop-2-yl






16




H




2-tert.-Butylthioprop-2-yl






17




H




Methyl






18




H




Ethyl






19




H




n-Propyl






20




H




iso-Propyl






21




H




n-Butyl






22




H




iso-Butyl






23




H




sec.-Butyl






24




H




tert.-Butyl






25




H




n-Hexyl






26




H




n-Decyl






27




H




Cyclopropyl






28




H




Cyclohexyl






29




H




Phenylthiomethyl






30




H




2-Phenylthiomethyl






31




H




2-(2′-Chlorophenylthio)prop-2-yl






32




H




Ethynyl






33




H




1-Propynyl






34




H




Methoxy






35




H




Ethoxy






36




H




n-Propoxy






37




H




iso-Propoxy






38




H




n-Butoxy






39




H




iso-Butoxy






40




H




sec.-Butoxy






41




H




tert.-Butoxy






42




H




Methylthio






43




H




Ethylthio






44




H




n-Propylthio






45




H




iso-Propylthio






46




H




n-Butylthio






47




H




iso-Butyl






48




H




sec.-Butyl






49




H




tert.-Butyl






50




H




Benzylthio






51




H




Trifluoromethoxy






52




H




Cyano






53




H




Amin






54




H




Methylamino






55




H




Dimethylamino






56




H




Ethylamino






57




H




Diethylamino






58




H




Di-n-Propylamino






59




H




Di-iso-Propylamino






60




H




Di-n-Butylamino






61




H




Di-iso-Butylamino






62




H




Acetyl






63




H




Propion-1-yl






64




H




Butyr-1-yl






65




H




iso-Butyr-1-yl






66




H




Pivaloyl






67




H




Benzoyl






68




H




4-Chlorobenzoyl






69




H




Benzylcarbonyl






70




H




Methoxycarbonyl






71




H




Ethoxycarbonyl






72




H




n-Propoxycarbonyl






73




H




iso-Propoxycarbonyl






74




H




n-Butoxycarbonyl






75




H




iso-Butoxycarbonyl






76




H




sec.-Butoxycarbonyl






77




H




tert.-Butoxycarbonyl






78




H




n-Hexoxycarbonyl






79




H




Phenoxycarbonyl






80




H




4-Chlorophenoxycarbonyl






81




H




Benzyloxycarbonyl






82




H




Aminocarbonyl






83




H




Dimethylaminocarbonyl






84




H




Diethylaminocarbonyl






85




H




Di-iso-Propylaminocarbonyl






86




H




Phenylaminocarbonyl






87




H




N-Methyl-N-Phenylamino-








carbonyl






88




H




Phenyl






89




H




2-Fluorophenyl




m.p.: 69-71° C.






90




H




3-Fluorophenyl




m.p.: 74-77° C.






91




H




4-Fluorophenyl




m.p.: 73-76° C.









IR (KBr): 1699,









1278, 1271, 1256,









1225






92




H




Pentafluorophenyl




m.p.: 94-96° C.;









IR (KBr): 1704,









1527, 1494, 1133






93




H




2-Chlorophenyl






1


H-NMR (CDCl


3


):









δ = 3.70s,









3.82s, 5.15s, 7.15-









7.40m, 7.52m,









7.60s, 7.85m, 8.52s






94




H




3-Chlorophenyl




m.p.: 48-50° C.;






95




H




4-Chlorophenyl




(v. Example 6)






96




H




Pentachlorophenyl






97




H




2,3-Dichlorophenyl




m.p.: 103-105° C.;






98




H




2,4-Dichlorophenyl




m.p.: 94-96° C.;






99




H




2,5-Dichlorophenyl






100




H




2,6-Dichlorophenyl




m.p.: 118-120° C.;






101




H




3,4-Dichlorophenyl




m.p.: 82-84° C.;






102




H




3,5-Dichlorophenyl




m.p.: 94-96° C.;






103




H




2,3,4-Trichlorophenyl






104




H




2,3,5-Trichlorophenyl






105




H




2,3,6-Trichlorophenyl






106




H




2,4,5-Trichlorophenyl






107




H




2,3,6-Trichlorophenyl






108




H




3,4,5-Trichlorophenyl






109




H




2,3,4,6-Tetrachlorophenyl






110




H




2,3,5,6-Tetrachlorophenyl






111




H




2-Bromophenyl




m.p.: 85-87° C.;






112




H




3-Bromophenyl






1


H-NMR (CDCl


3


):









δ = 3.68s, 3.79s,









5.13, 7.15-7.54 m,









7.59s 7.74s, 8.00s






113




H




4-Bromophenyl




m.p.: 131-134° C.;






114




H




2,4-Dibromophenyl






115




H




3-Brom-4-fluorophenyl






116




H




3-Brom-4-methoxyphenyl






117




H




2-Iodophenyl






118




H




3-Iodophenyl






119




H




4-Iodophenyl






120




H




2-Chloro-4-fluorophenyl




m.p.: 112-115° C.;






121




H




2-Chloro-5-fluorophenyl






122




H




2-Chloro-6-fluorophenyl




m.p.: 80-82° C.;






123




H




2-Chloro-4-bromophenyl






124




H




2-Bromo-4-chlorophenyl






125




H




2-Bromo-4-bromophenyl






126




H




3-Bromo-4-chlorophenyl






127




H




3-Chloro-4-fluorophenyl






128




H




3-Fluoro-4-chlorophenyl






129




H




2-Cyanophenyl






130




H




3-Cyanophenyl






131




H




4-Cyanophenyl






132




H




2-Nitrophenyl






133




H




3-Nitrophenyl






134




H




4-Nitrophenyl




m.p.: 147-155° C.;






135




H




2-Methylphenyl




m.p.: 57-59° C.;






136




H




3-Methylphenyl




m.p.: 54-56° C.;






137




H




4-Methylphenyl




m.p.: 86-88° C.;






138




H




2,4-Dimethylphenyl




m.p.: 75-77° C.;






139




H




2,6-Dimethylphenyl






140




H




3,4-Dimethylphenyl






141




H




3,5-Dimethylphenyl






142




H




2,3,4-Trimethylphenyl






143




H




2,3,5-Trimethylphenyl






144




H




2,3,6-Trimethylphenyl






145




H




2,4,5-Trimethylphenyl






146




H




2,4,6-Trimethylphenyl






147




H




3,4,5-Trimethylphenyl






148




H




Pentamethylphenyl






149




H




2-Ethylphenyl






150




H




3-Ethylphenyl






151




H




4-Ethylphenyl






152




H




3,5-Diethylphenyl






153




H




2-n-Propylphenyl






154




H




3-n-Propylphenyl






155




H




4-n-Propylphenyl






156




H




2-iso-Propylphenyl






157




H




3-iso-Propylphenyl






158




H




4-iso-Propylphenyl






159




H




2,4-Di-iso-Propylphenyl






160




H




3,5-Di-iso-Propylphenyl






161




H




4-n-Butylphenyl






162




H




4-sec.-Butylphenyl






163




H




4-iso-Butylphenyl






164




H




4-tert.-Butylphenyl




m.p.: 71-73° C.






165




H




3-tert.-Butylphenyl






166




H




2-tert.-Butylphenyl






167




H




2,4-Di-tert.-Butylphenyl






168




H




3,5-Di-tert.-Butylphenyl






169




H




4-n-Hexylphenyl






170




H




4-n-Dodecylphenyl






171




H




2-Methyl-4-tert.-Butylphenyl






172




H




2-Methyl-6-tert.-Butylphenyl






173




H




2-Methyl-4-iso-Butylphenyl






174




H




2-Methyl-4-cyclohexylphenyl






175




H




2-Methyl-4-phenylphenyl






176




H




2-Methyl-4-benzylphenyl






177




H




2-Methyl-4-phenoxyphenyl






178




H




2-Methyl-4-benzyloxyphenyl






179




H




2-Methyl-3-chlorophenyl






180




H




2-Methyl-4-chlorophenyl






181




H




2-Methyl-5-chlorophenyl






182




H




2-Methyl-6-chlorophenyl






183




H




2-Methyl-4-fluorophenyl






184




H




2-Methyl-3-bromophenyl






185




H




2-Methyl-4-bromophenyl






186




H




2-Methyl-3-methoxyphenyl






187




H




2-Methyl-4-methoxyphenyl






188




H




2-Methyl-5-methoxyphenyl






189




H




2-Methyl-6-methoxyphenyl






190




H




2-Methyl-4-iso-Propoxyphenyl






191




H




2-Methyl-2,5-dimethoxyphenyl






192




H




2-Methoxyphenyl




m.p.: 52-54° C.






193




H




3-Methoxyphenyl






1


H-NMR (CDCl


3


):









δ = 3.65s,









3.76s, 3.80s, 5.12s,









6.88-7.54m, 7.58s









8.05s






194




H




4-Methoxyphenyl




m.p.: 61-63° C.






195




H




2,3-Dimethoxyphenyl






196




H




2,4-Dimethoxyphenyl




m.p.: 70-72° C.






197




H




2,5-Dimethoxyphenyl






198




H




2,6-Dimethoxyphenyl






199




H




3,4-Dimethoxyphenyl






200




H




3,5-Dimethoxyphenyl




m.p.: 79-82° C.






201




H




3,6-Dimethoxyphenyl






202




H




2,3,4-Trimethoxyphenyl






203




H




2,3,5-Trimethoxyphenyl






204




H




2,3,6-Trimethoxyphenyl






205




H




2,4,5-Trimethoxyphenyl






206




H




2,3,6-Trimethoxyphenyl






207




H




3,4,5-Trimethoxyphenyl






208




H




2-Ethoxyphenyl






209




H




3-Ethoxyphenyl






1


H-NMR (CDCl


3


):









δ = 1.39t,









3.67s, 3.80s, 4.02q,









5.12s, 6.87-









7.54m, 7.58s, 8.05s






210




H




4-Ethoxyphenyl




m.p.: 93-94° C.






211




H




2-iso-Propoxyphenyl






212




H




3-iso-Propoxyphenyl






213




H




4-iso-Propoxyphenyl






214




H




3-tert.-Butoxyphenyl






215




H




4-tert.-Butoxyphenyl






1


H-NMR (CDCl


3


):









δ = 1.36s,









3.68s, 3.78s, 5.09s,









6.94-7.53m,









7.58s, 8.07s






216




H




2-Trifluoromethoxyphenyl






217




H




3-Trifluoromethoxyphenyl






218




H




4-Trifluoromethoxyphenyl






219




H




3-(1′,1′,2′,2′-








Tetrafluoro)ethoxyphenyl






220




H




4-(1′,1′,2′,2′-








Tetrafluoro)ethoxyphenyl






221




H




2-Chloromethylphenyl






222




H




3-Chloromethylphenyl






223




H




4-Chloromethylphenyl






224




H




2-Trifluoromethylphenyl




m.p.: 75-77° C.






225




H




3-Trifluoromethylphenyl






226




H




4-Trifluoromethylphenyl




m.p.: 111-114° C.






227




H




2-(Methoxyiminomethyl)phenyl






228




H




3-(Methoxyiminomethyl)phenyl






229




H




4-(Methoxyiminomethyl)phenyl






230




H




2-(Ethoxyiminomethyl)phenyl






231




H




3-(Ethoxyiminomethyl)phenyl






232




H




4-(Ethoxyiminomethyl)phenyl






233




H




2-(n-Propoxyiminomethyl)phenyl






234




H




3-(n-Propoxyiminomethyl)phenyl






235




H




4-(n-Propoxyiminomethyl)phenyl






236




H




2-(iso-Propoxyiminomethyl)-








phenyl






237




H




3-(iso-Propoxyiminomethyl)-








phenyl






238




H




4-(iso-Propoxyiminomethyl)-








phenyl






239




H




2-(n-Butoxyiminomethyl)phenyl






240




H




3-(n-Butoxyiminomethyl)phenyl






241




H




4-(n-Butoxyiminomethyl)phenyl






242




H




2-(iso-Butoxyiminomethyl)phenyl






243




H




3-(iso-Butoxyiminomethyl)phenyl






244




H




4-(iso-Butoxyiminomethyl)phenyl






245




H




2-(tert.-Butoxyiminomethyl)-








phenyl






246




H




3-(tert.-Butoxyiminomethyl)-








phenyl






247




H




4-(tert.-Butoxyiminomethyl)-








phenyl






248




H




2-(n-Pentoxyiminomethyl)phenyl






249




H




3-(n-Pentoxyiminomethyl)phenyl






250




H




4-(n-Pentoxyiminomethyl)phenyl






251




H




2-(n-Hexoxyiminomethyl)phenyl






252




H




3-(n-Hexoxyiminomethyl)phenyl






253




H




4-(n-Hexoxyiminomethyl)phenyl






254




H




2-(Allyloxyiminomethyl)phenyl






255




H




3-(Allyloxyiminomethyl)phenyl






256




H




4-(Allyloxyiminomethyl)phenyl






257




H




2-(Benzyloxyiminomethyl)phenyl






258




H




3-(Benzyloxyiminomethyl)phenyl






259




H




4-(Benzyloxyiminomethyl)phenyl






260




H




2-(Methoxyimino-1′-ethyl)phenyl






261




H




3-(Methoxyimino-1′-ethyl)phenyl






262




H




4-(Methoxyimino-1′-ethyl)phenyl






263




H




2-(Ethoxyimino-1′-ethyl)phenyl






264




H




3-(Ethoxyimino-1′-ethyl)phenyl






265




H




4-(Ethoxyimino-1′-ethyl)phenyl






266




H




2-(n-Propoxyimino-1′-ethyl)-








phenyl






267




H




3-(n-Propoxyimino-1′-ethyl)-








phenyl






268




H




4-(n-Propoxyimino-1′-ethyl)-








phenyl






269




H




2-(n-Butoxyamino-1′-ethyl)phenyl






270




H




3-(n-Butoxyamino-1′-ethyl)phenyl






271




H




4-(n-Butoxyamino-1′-ethyl)phenyl






272




H




2-(n-Pentoxyimino-1′-ethyl)-








phenyl






273




H




3-(n-Pentoxyimino-1′-ethyl)-








phenyl






274




H




4-(n-Pentoxyimino-1′-ethyl)-








phenyl






275




H




2-(n-Hexoxyimino-1′-ethyl)phenyl






276




H




3-(n-Hexoxyimino-1′-ethyl)phenyl






277




H




4-(n-Hexoxyimino-1′-ethyl)phenyl






278




H




2-(Allyloxyimino-1′-ethyl)phenyl






279




H




3-(Allyloxyimino-1′-ethyl)phenyl






280




H




4-(Allyloxyimino-1′-ethyl)phenyl






281




H




2-(Benzyloxyimino-1′-ethyl)-








phenyl






282




H




3-(Benzyloxyimino-1′-ethyl)-








phenyl






283




H




4-(Benzyloxyimino-1′-ethyl)-








phenyl






284




H




2-Phenylphenyl






285




H




3-Phenylphenyl






286




H




4-Phenylphenyl




m.p.: 94-96° C.






287




H




2-Phenoxyphenyl






288




H




3-Phenoxyphenyl






289




H




4-Phenoxyphenyl






290




H




2-Benzyloxyphenyl






291




H




3-Benzyloxyphenyl






292




H




4-Benzyloxyphenyl




m.p.: 94-96° C.






293




H




4-(Imidazol-1′-yl)phenyl






294




H




4-(Piperazin-1′-yl)phenyl






295




H




4-(Morpholin-1′-yl)phenyl






296




H




4-(Piperazin-1′-yl)phenyl






297




H




4-(Pyridyl-2′-oxy)phenyl






298




H




2-Cyclopropylphenyl






299




H




3-Cyclopropylphenyl






300




H




4-Cyclopropylphenyl






301




H




3-Cyclohexylphenyl






302




H




4-Cyclohexylphenyl






303




H




4-Oxiramylphenyl






304




H




4-(1′,3′-Dioxo-2′-yl)phenyl






305




H




4-(Tetrahydropyran-2-yloxy)-








phenyl






306




H




1-Naphthyl






307




H




2-Naphthyl




oil: IR (film): 1707,









1633, 1257, 1129, 110






308




H




9-Anthryl






309




H




1-Naphthoxy






310




H




2-Naphthoxy






311




H




9-Anthroxy






312




H




Phenoxy






313




H




2-Chlorophenoxy






314




H




3-Chlorophenoxy






315




H




4-Chlorophenoxy






316




H




4-Methylphenoxy






317




H




4-tert.-Butylphenoxy






318




H




4-Methylphenoxy






319




H




4-Ethoxyphenoxy






320




H




4-tert.-Butoxyphenoxy






321




H




Phenylthio






322




H




2-Chlorophenylthio






323




H




4-Chlorophenylthio






324




H




Benzyl






325




H




2-Methylbenzyl






326




H




3-Methylbenzyl






327




H




4-Methylbenzyl






328




H




4-tert.-Butylbenzyl






329




H




2-Chlorobenzyl






330




H




3-Chlorobenzyl






331




H




4-Chlorobenzyl






332




H




2,4-Dichlorobenzyl






333




H




2,6-Dichlorobenzyl






334




H




2,4,6-Trichlorobenzyl






335




H




2-Trifluoromethylbenzyl






336




H




3-Trifluoromethylbenzyl






337




H




4-Trifluoromethylbenzyl






338




H




2-Methoxybenzyl






339




H




4-Methoxybenzyl






340




H




4-tert.-Butoxybenzyl






341




H




4-Phenoxybenzyl






342




H




1-Phenethyl






343




H




2-Phenethyl






344




H




1-Phenylpropyl






345




H




2-Phenylpropyl






346




H




3-Phenylpropyl






347




H




2-Methyl-2-phenylpropyl






348




H




2-Methyl-3-phenylpropyl






349




H




4-Phenylbutyl






350




H




2-Phenyl-1-ethenyl






351




H




1-Phenyl-1-ethenyl






352




H




1-Phenyl-1-propenyl






353




H




1-Phenyl-1-propen-2-yl






354




H




2,2-Diphenylethenyl






355




H




Phenoxymethyl






356




H




2-Pyridyl






357




H




3-Pyridyl






358




H




4-Pyridyl






359




H




2,6-Pyrimidinyl






360




H




1,5-Pyrimidinyl






361




H




2-Thienyl






362




H




3-Thienyl






363




H




2-Furyl






364




H




3-Furyl






365




H




1-Pyrrolyl






366




H




1-Imidazolyl






367




H




1,2,4-Triazolyl






368




H




1,3,4-Triazolyl






369




H




4-Thiazolyl






370




H




2-Benzothiazolyl






371




H




2-Pyridyloxy






372




H




2-Pyrimidinyloxy






373




H




2-Pyridylthio






374




H




2-Pyrimidinylthio






375




H




2-Benzothiazolylthio






376




H




Phenylthiomethyl






377




H




2-Pyridylmethyl






378




H




3-Pyridylmethyl






379




H




Furfuryloxy






380




H




Thienylmethoxy






381




H




3-Isoxazolylmethoxy






382




H




2-Oxazolylmethoxy






383




H




2-Pyridylmethoxy






384




H




2′-Furyl-2-ethenyl






385




H




2′-Thienyl-2-thenyl






386




H




3′-Pyridyl-2-ethenyl






387




H




Oxiranyl






388




H




1-Azinidiayl






389




H




1-Azetidinyl






390




H




1-Pyrrolidinyl






391




H




2-Tetrahydrofuryl






392




H




2-Tetrahydropyranyl






393




H




3-Tetrahydropyranyl






394




H




1-Piperidinyl






395




H




1-Morpholinyl






396




H




1-Piperazinyl






397




H




1,3-Dioxan-2-yl






398




H




3-Tetrahydrothiopyranyl






399




H




2-Dihydropyranyloxy






400




H




2-Tetrahydropyranyloxy






401




H




CF


3








402




H




2-Fluoroethyl






403




H




2,2,2-Trifluoroethyl






404




H




Pentafluoroethyl






405




H




Chloromethyl






406




H




Dichloromethyl






407




H




Trichloromethyl






408




H




2-Chloroethyl






409




H




2,2,2-Trichloroethyl






410




H




Pentachoroethyl






411




H




Cyclopropyl






412




H




Cycloburyl






413




H




Cyclopentyl






414




H




Cyclohexyl






415




H




1-Methylcyclopropyl






416




H




2,2-Dimethylcyclopropyl






417




H




1-Methylcyclohexyl






418




H




2,2-Difluorocyclopropyl






419




H




2,2-Dichlorocyclopropyl






420




H




2,2-Dibromocyclopropyl






421




H




2,2-Dichloro-3-Methylcyclo-








propyl






422




H




2,2,3,3-Tetrafluorocyclobutyl






423




H




Ethenyl






424




H




1-Propenyl






425




H




2-Methyl-1-propenyl






426




H




4-Methylpem-3-en-1-yl






427




H




2-Propenyl






428




H




2-Butenyl






429




H




2-Methyl-1-propenyl






430




H




3-Methyl-2-butenyl






431




H




2,2-Difluoroethenyl






432




H




2,2-Dichloroethenyl






433




H




3,3,3-Trifluoropropenyl






434




H




3,3,3-Trichloropropenyl






435




H




3-Chloro-2-propenyl






436




H




Cyclopent-1-enyl






437




H




Cyclopentadienyl






438




H




Cyclohex-1-enyl






439




H




Pentafluorocyclopentadienyl






440




H




Pentachlorocyclopentadienyl






441




H




4-Dimethylaminophenyl




m.p.: 90-92° C.






442




H




4-n-Butoxyphenyl




m.p.: 79-82° C.






















TABLE VI








































No.




R


3






R


4






Data

















1




H




H




m.p.: 94-95° C.






2




H




Methoxymethyl






3




H




Ethoxymethyl






4




H




n-Propoxymethyl






5




H




iso-Propoxymethyl






6




H




tert.-Butoxymethyl






7




H




2-Methoxyprop-2-yl






8




H




2-Ethoxyprop-2-yl






9




H




2-n-Propoxyprop-2-yl






10




H




2-iso-Propoxyprop-2-yl






11




H




2-tert.-Butoxyprop-2-yl






12




H




Methylthiomethyl






13




H




tert.-Butylthiomethyl






14




H




2-Methylthioprop-2-yl






15




H




2-iso-Propylthioprop-2-yl






16




H




2-tert.-Butylthioprop-2-yl






17




H




Methyl






18




H




Ethyl






19




H




n-Propyl






20




H




iso-Propyl






21




H




n-Butyl






22




H




iso-Butyl






23




H




sec.-Butyl






24




H




tert.-Butyl






25




H




n-Hexyl






26




H




n-Decyl






27




H




Cyclopropyl






28




H




Cyclohexyl






29




H




Phenylthiomethyl






30




H




2-Phenylthiomethyl






31




H




2-(2′-Chlorophenylthio)prop-2-yl






32




H




Ethynyl






33




H




I-Propynyl






34




H




Methoxy






35




H




Ethoxy






36




H




n-Propoxy






37




H




iso-propoxy






38




H




n-Butoxy






39




H




iso-Butoxy






40




H




sec.-Butoxy






41




H




tert.-Butoxy






42




H




Methylthio






43




H




Ethylthio






44




H




n-Propylthio






45




H




iso-Propylthio






46




H




n-Butylthio






47




H




iso-Butylthio






48




H




sec.-Butylthio






49




H




tert.-Butylthio






50




H




Benzylthio






51




H




Trifluoromethoxy






52




H




Cyano






53




H




Amino






54




H




Methylamino






55




H




Dimethylamino






56




H




Ethylamino






57




H




Diethylamino






58




H




Di-n-Propylamino






59




H




Di-iso-Propylamino






60




H




Di-n-Butylamino






61




H




Di-iso-Butylamino






62




H




Acetyl






63




H




Propion-1-yl






64




H




Butyr-1-yl






65




H




iso-Butyr-1-yl






66




H




Pivaloyl






67




H




Benzoyl






68




H




4-Chlorobenzoyl






69




H




Benzylcarbonyl






70




H




Methoxycarbonyl






71




H




Ethoxycarbonyl






72




H




n-Propoxycarbonyl






73




H




iso-Propoxycarbonyl






74




H




n-Butoxycarbonyl






75




H




iso-Butoxycarbonyl






76




H




sec.-Butoxycarbonyl






77




H




tert.-Butoxycarbonyl






78




H




n-Hexoxycarbonyl






79




H




Phenoxycarbonyl






80




H




4-Chlorophenoxycarbonyl






81




H




Benzyloxycarbonyl






82




H




Aminocarbonyl






83




H




Dimethylaminocarbonyl






84




H




Diethylaminocarbonyl






85




H




Di-iso-Propylaminocarbonyl






86




H




Phenylaminocarbonyl






87




H




N-Methyl-N-Phenylamino-








carbonyl






88




H




Phenyl




m.p.: 92-95° C.






89




H




2-Fluorophenyl




m.p.: 92-95° C.






90




H




3-Fluorophenyl




m.p.: 58-60° C.






91




H




4-Fluorophenyl




m.p.: 110-111° C.






92




H




Pentafluorophenyl




m.p.: 118-120° C.






93




H




2-Chlorophenyl






1


H—NMR (CDCl


3


):









δ = 3.70s,









3.82s, 5.15s, 7.15-









7.40m, 7.52m,









7.60s, 7.85m, 8.52s






94




H




3-Chlorophenyl




m.p.: 58-60° C.






95




H




4-Chlorophenyl




m.p.: 146-148° C.






96




H




Pentachlorophenyl






97




H




2,3-Dichlorophenyl




m.p.: 95-97° C.






98




H




2,4-Dichlorophenyl




m.p.: 58-62° C.






99




H




2,5-Dichlorophenyl






100




H




2,6-Dichlorophenyl




m.p.: 136-140° C.






101




H




3,4-Dichlorophenyl




m.p.: 94-97° C.






102




H




3,5-Dichlorophenyl




m.p.: 88-91° C.






103




H




2,3,4-Trichlorophenyl






104




H




2,3,5-Trichlorophenyl






105




H




2,3,6-Trichlorophenyl






106




H




2,4,5-Trichlorophenyl






107




H




2,4,6-Trichlorophenyl






108




H




3,4,5-Trichlorophenyl






109




H




2,3,4,6-Tetrachlorophenyl






110




H




2,3,5,6-Tetrachlorophenyl






111




H




2-Bromophenyl




m.p.: 91-94° C.






112




H




3-Bromophenyl




m.p.: 63-64° C.






113




H




4-Bromophenyl




m.p.: 145-147° C.






114




H




2,4-Dibromophenyl






115




H




3-Bromo-4-Fluorophenyl






116




H




3-Bromo-4-Methoxyphenyl






117




H




2-Iodophenyl






118




H




3-Iodophenyl






119




H




4-Iodophenyl






120




H




2-Chloro-4-Fluorophenyl




m.p.: 90-93° C.






121




H




2-Chloro-5-Fluorophenyl






122




H




2-Chloro-6-Fluorophenyl




m.p.: 111-113° C.






123




H




2-Chloro-4-Bromophenyl






124




H




2-Bromo-4-Chlorophenyl






125




H




2-Bromo-4-Fluorophenyl






126




H




3-Bromo-4-Chlorophenyl






127




H




3-Chloro-4-Fluorophenyl






128




H




3-Fluoro-4-Chlorophenyl






129




H




2-Cyanophenyl






130




H




3-Cyanophenyl






131




H




4-Cyanophenyl






132




H




2-Nitrophenyl






133




H




3-Nitrophenyl






134




H




4-Nitrophenyl




m.p.: 142-146° C.






135




H




2-Methylphenyl




m.p.: 58-60° C.






136




H




3-Methylphenyl




m.p.: 70-72° C.






137




H




4-Methylphenyl




m.p.: 99-102° C.






138




H




2,4-Dimethylphenyl




m.p.: 54-56° C.






139




H




2,6-Dimethylphenyl






140




H




3,4-Dimethylphenyl






141




H




3,5-Dimethylphenyl






142




H




2,3,4-Trimethylphenyl






143




H




2,3,5-Trimethylphenyl






144




H




2,3,6-Trimethylphenyl






145




H




2,4,5-Trimethylphenyl






146




H




2,4,6-Trimethylphenyl






147




H




3,4,5-Trimethylphenyl






148




H




Pentamethylphenyl






149




H




2-Ethylphenyl






150




H




3-Ethylphenyl






151




H




4-Ethylphenyl






152




H




3,5-Diethylphenyl






153




H




2-n-Propylphenyl






154




H




3-n-Propylphenyl






155




H




4-n-Propylphenyl






156




H




2-iso-Propylphenyl






157




H




3-iso-Propylphenyl






158




H




4-iso-Propylphenyl






159




H




2,4-Di-iso-Propylphenyl






160




H




3,5-Di-iso-Propylphenyl






161




H




4-n-Butylphenyl






162




H




4-sec.-Butylphenyl






163




H




4-iso-Butylphenyl






164




H




4-tert.-Butylphenyl




m.p.: 82-84° C.






165




H




3-tert.-Butylphenyl






166




H




2-tert.-Butylphenyl






167




H




2,4-Di-tert.-Butylphenyl






168




H




3,5-Di-tert.-Butylphenyl






169




H




4-n-Hexylphenyl






170




H




4-n-Dodecylphenyl






171




H




2-Methyl-4-tert.-Butylphenyl






172




H




2-Methyl-6-tert.-Butylphenyl






173




H




2-Methyl-4-iso-Propylphenyl






174




H




2-Methyl-4-Cyclohexylphenyl






175




H




2-Methyl-4-Phenylphenyl






176




H




2-Methyl-4-Benzylphenyl






177




H




2-Methyl-4-Phenoxyphenyl






178




H




2-Methyl-4-Benzyloxyphenyl






179




H




2-Methyl-3-Chlorophenyl






180




H




2-Methyl-4-Chlorophenyl






181




H




2-Methyl-5-Chlorophenyl






182




H




2-Methyl-6-Chlorophenyl






183




H




2-Methyl-4-Fluorophenyl






184




H




2-Methyl-3-Bromophenyl






185




H




2-Methyl-4-Bromophenyl






186




H




2-Methyl-3-Methoxyphenyl






187




H




2-Methyl-4-Methoxyphenyl






188




H




2-Methyl-5-Methoxyphenyl






189




H




2-Methyl-6-Methoxyphenyl






190




H




2-Methyl-4-iso-Propoxyphenyl






191




H




2-Methyl-2,5-Dimethoxyphenyl






192




H




2-Methoxyphenyl




m.p.: 65-68° C.






193




H




3-Methoxyphenyl




m.p.: 83-84° C.






194




H




4-Methoxyphenyl




m.p.: 88-90° C.






195




H




2,3-Dimethoxyphenyl






196




H




2,4-Dimethoxyphenyl




m.p.: 90-93° C.






197




H




2,5-Dimethoxyphenyl






198




H




2,6-Dimethoxyphenyl






199




H




3,4-Dimethoxyphenyl




m.p.: 70-72° C.






200




H




3,5-Dimethoxyphenyl




m.p.: 92-99° C.






201




H




3,6-Dimethoxyphenyl






202




H




2,3,4-Trimethoxyphenyl






203




H




2,3,5-Trimethoxyphenyl






204




H




2,3,6-Trimethoxyphenyl






205




H




2,4,5-Trimethoxyphenyl






206




H




2,4,6-Trimethoxyphenyl






207




H




3,4,5-Trimethoxyphenyl




m.p.: 105-109° C.






208




H




2-Ethoxyphenyl






209




H




3-Ethoxyphenyl




m.p.: 90-92° C.






210




H




4-Ethoxyphenyl




m.p.: 97-98° C.






211




H




2-iso-Propoxyphenyl






212




H




3-iso-Propoxyphenyl






213




H




4-iso-Propoxyphenyl






214




H




3-tert.-Butoxyphenyl






215




H




4-tert.-Butoxyphenyl




m.p.: 78-83° C.






216




H




2-Trifluoromethoxyphenyl






217




H




3-Trifluoromethoxyphenyl






218




H




4-Trifluoromethoxyphenyl






219




H




3-(1′,1′,2′,2′-








Tetrafluoro)ethoxyphenyl






220




H




4-(1′,1′,2′,2′-








Tetrafluoro)ethoxyphenyl






221




H




2-Chloromethylphenyl






222




H




3-Chloromethylphenyl






223




H




4-Chloromethylphenyl






224




H




2-Trifluoromethylphenyl




m.p.: 58-60° C.






225




H




3-Trifluoromethylphenyl




m.p.: 74-77° C.






226




H




4-Trifluoromethylphenyl




m.p.: 120-122° C.






227




H




2-(Methoxyiminomethyl)phenyl






228




H




3-(Methoxyiminomethyl)phenyl






229




H




4-(Methoxyiminomethyl)phenyl






230




H




2-(Ethoxyiminomethyl)phenyl






231




H




3-(Ethoxyiminomethyl)phenyl






232




H




4-(Ethoxyiminomethyl)phenyl






233




H




2-(n-Propoxyiminomethyl)phenyl






234




H




3-(n-Propoxyiminomethyl)phenyl






235




H




4-(n-Propoxyiminomethyl)phenyl






236




H




2-(iso-Propoxyiminomethy)-








phenyl






237




H




3-(iso-Propoxyiminomethyl)-








phenyl






238




H




4-(iso-Porpoxyiminomethyl)-








phenyl






239




H




2-(n-Butoxyiminomethyl)phenyl






240




H




3-(n-Butoxyiminomethyl)phenyl






241




H




4-(n-Butoxyiminomethyl)phenyl






242




H




2-(iso-Butoxyiminomethyl)phenyl






243




H




3-(iso-Butoxyiminomethyl)phenyl






244




H




4-(iso-Butoxyiminomethyl)phenyl






245




H




2-(tert.-Butoxyiminomethyl)-








phenyl






246




H




3-(tert.-Butoxyiminomethyl)-








phenyl






247




H




4-(tert.-Butoxyiminomethyl)-








phenyl






248




H




2-(n-Pentoxyiminomethyl)phenyl






249




H




3-(n-Pentoxyiminomethyl)phenyl






250




H




4-(n-Pentoxyiminomethyl)phenyl






251




H




2-(n-Hexoxyiminomethyl)phenyl






252




H




3-(n-Hexoxyiminomethyl)phenyl






253




H




4-(n-Hexoxyiminomethyl)phenyl






254




H




2-(Allyloxyiminomethyl)phenyl






255




H




3-(Allyloxyiminomethyl)phenyl






256




H




4-(Allyloxyiminomethyl)phenyl






257




H




2-(Benzyloxyiminomethyl)phenyl






258




H




3-(Benzyloxyiminomethyl)phenyl






259




H




4-(Benzyloxyiminomethyl)phenyl






260




H




2-(Methoxyimino-1′-ethyl)phenyl






261




H




3-(Methoxyimino-1′-ethyl)phenyl






262




H




4-(Methoxyimino-1′-ethyl)phenyl






263




H




2-(Ethoxyimino-1′-ethyl)phenyl






264




H




3-(Ethoxyimino-1′-ethyl)phenyl






265




H




4-(Ethoxyimino-1′-ethyl)phenyl






266




H




2-(n-Propoxyimino-1′-ethyl)-








phenyl






267




H




3-(n-Propoxyimino-1′-ethyl)-








phenyl






268




H




4-(n-Propoxyimino-1′-ethyl)-








phenyl






269




H




2-(n-Butoxyamino-1′-ethyl)phenyl






270




H




3-(n-Butoxyamino-1′-ethyl)phenyl






271




H




4-(n-Butoxyamino-1′-ethyl)phenyl






272




H




2-(n-Pentoxyimino-1′-ethyl)-








phenyl






273




H




3-(n-Pentoxyimino-1′-ethyl)-








phenyl






274




H




4-(n-Pentoxyimino-1′-ethyl)-








phenyl






275




H




2-(n-Hexoxyimino-1′-ethyl)phenyl






276




H




3-(n-Hexoxyimino-1′-ethyl)phenyl






277




H




4-(n-Hexoxyimino-1′-ethyl)phenyl






278




H




2-(Allyloxyimino-1′-ethyl)phenyl






279




H




3-(Allyloxyimino-1′-ethyl)phenyl






280




H




4-(Allyloxyimino-1′-ethyl)phenyl






281




H




2-(Benzyloxyimino-′-ethyl)-








phenyl






282




H




3-(Benzyloxyimino-1′-ethyl)-








phenyl






283




H




4-(Benzyloxyimino-1′-ethyl)-








phenyl






284




H




2-Phenylphenyl






285




H




3-Phenylphenyl






286




H




4-Phenylphenyl




m.p.: 100-102° C.






287




H




2-Phenoxyphenyl






288




H




3-Phenoxyphenyl




IR (film): 1728,









1489, 1247, 1214,









1070, 1020






289




H




4-Phenoxyphenyl




m.p.: 85-87° C.






290




H




2-Benzyloxyphenyl




m.p.: 83-85° C.






291




H




3-Benzyloxyphenyl




m.p.: 66-68° C.






292




H




4-Benzyloxyphenyl




m.p.: 104-106° C.






293




H




4-(Imidazol-1′-yl)phenyl






294




H




4-(Piperazin-1′-yl)phenyl






295




H




4-(Morpholin-1′-yl)phenyl






296




H




4-(Piperazin-1′-yl)phenyl






297




H




4-(Pyridyl-2′-oxy)phenyl






298




H




2-Cyclopropylphenyl






299




H




3-Cyclopropylphenyl






300




H




4-Cyclopropylphenyl






301




H




3-Cyclohexylphenyl






302




H




4-Cyclohexylphenyl






303




H




4-Oxiranylphenyl






304




H




4-(1′,3′-Dioxan-2′-yl)phenyl






305




H




4-(Tetrahydropyran-2-yloxy)-








phenyl






306




H




1-Naphthyl




m.p.: 70-73° C.






307




H




2-Naphyhyl




m.p.: 125-126° C.






308




H




9-Anthryl






309




H




1-Naphthoxy






310




H




2-Naphthoxy






311




H




9-Anthroxy






312




H




Phenoxy






313




H




2-Chlorophenoxy






314




H




3-Chlorophenoxy






315




H




4-Chlorophenoxy






316




H




4-Methylphenoxy






317




H




4-tert.-Butylphenoxy






318




H




4-Methoxyphenoxy






319




H




4-Ethoxyphenoxy






320




H




4-tert.-Butoxyphenoxy






321




H




Phenylthio






322




H




2-Chlorophenylthio






323




H




4-Chlorophenylthio






324




H




Benzyl






325




H




2-Methylbenzyl






326




H




3-Methylbenzyl






327




H




4-Methylbenzyl






328




H




4-tert.-Butylbenzyl






329




H




2-Chlorobenzyl






330




H




3-Chlorobenzyl






331




H




4-Chlorobenzyl






332




H




2,4-Dichlorobenzyl






333




H




2,6-Dichlorobenzyl






334




H




2,4,6-Trichlorobenzyl






335




H




2-Trifluoromethylbenzyl






336




H




3-Trifluoromethylbenzyl






337




H




4-Trifluoromethylbenzyl






338




H




2-Methoxybenzyl






339




H




4-Methoxybenzyl






340




H




4-tert.-Butoxybenzyl






341




H




4-Phenoxybenzyl






342




H




1-Phenethyl






343




H




2-Phenethyl






344




H




1-Phenylpropyl






345




H




2-Phenylpropyl






346




H




3-Phenylpropyl






347




H




2-Methyl-2-phenylpropyl






348




H




2-Methyl-3-phenylpropyl






349




H




4-Phenylbutyl






350




H




2-Phenyl-1-ethenyl






351




H




1-Phenyl-1-ethenyl






352




H




1-Phenyl-1-propenyl






353




H




1-Phenyl-1-porpen-2-yl






354




H




2,2-Diphenylethenyl






355




H




Phenoxymethyl






356




H




2-Pyridyl






357




H




3-Pyridyl






358




H




4-Pyridyl






359




H




2,6-Pyrimidinyl






360




H




1,5-Pyrimidinyl






361




H




2-Thienyl






362




H




3-Thienyl






363




H




2-Furyl






364




H




3-Furyl






365




H




1-Pyrrolyl






366




H




1-Imidazolyl






367




H




1,2,4-Triamolyl






368




H




1,3,4-Triamolyl






369




H




4-Thiazolyl






370




H




2-Benzothiazolyl






371




H




2-Pyridyloxy






372




H




2-Pyrimidinyloxy






373




H




2-Pyridylthio






374




H




2-Pyrimidinylthio






375




H




2-Benzothimzolylthio






376




H




Phenylthiomethyl






377




H




2-Pyridylmethyl






378




H




3-Pyridylmethyl






379




H




Perfuryloxy






380




H




Thienylmethoxy






381




H




3-hexazolylmethoxy






382




H




2-Oxazolylmethoxy






383




H




2-Pyridylmethoxy






384




H




2′-Furyl-2-ethenyl






385




H




2′-Thienyl-2-ethenyl






386




H




3′-Pyridyl-2-ethenyl






387




H




Oxiramyl






388




H




1-Aziridinyl






389




H




1-Azazidinyl






390




H




1-Pyrrodidinyl






391




H




2-Tetrahydrofuryl






392




H




2-Tetrahydropyraryl






393




H




3-Tetrahydropyraryl






394




H




1-Piperidinyl






395




H




1-Morpholinyl






396




H




1-Piperazinyl






397




H




1,3-Dioxan-2-yl






398




H




3-Tetrahydrothiopyranyl






399




H




2-Dihydropyranyloxy






400




H




2-Tetrahydropyranyloxy






401




H




CF


3








402




H




2-Fluoroethyl






403




H




2,2,2-Trifluoroethyl






404




H




Pentafluoroethyl






405




H




Chloromethyl






406




H




Dichloromethyl






407




H




Trichloromethyl






408




H




2-Chloroethyl






409




H




2,2,2-Trichloroethyl






410




H




Pentachloroethyl






411




H




Cyclopropyl






412




H




Cyclobutyl






413




H




Cyclopentyl






414




H




Cyclohexyl






415




H




1-Methylcyclopropyl






416




H




2,2-Dimethylcyclopropyl






417




H




1-Methylcyclohexyl






418




H




2,2-Difluorocyclopropyl






419




H




2,2-Dichlorocyclopropyl






420




H




2,2-Dibromocyclopropyl






421




H




2,2-Dichloro-3-methylcyclo-








propyl






422




H




2,2,3,3-Tetrafluorocyclobutyl






423




H




Ethenyl






424




H




1-Propenyl






425




H




2-Methyl-1-propenyl






426




H




4-Methylpent-3-en-1-yl






427




H




2-Propenyl






428




H




2-Butenyl






429




H




1-Methyl-2-propenyl






430




H




3-Methyl-2-butenyl






431




H




2,2-Difluoroethenyl






432




H




2,2-Dichloroethenyl






433




H




3,3,3-Trifluoropropenyl






434




H




3,3,3-Trichloropropenyl






435




H




3-Chloro-2-propenyl






436




H




Cyclopent-1-enyl






437




H




Cyclopentadienyl






438




H




Cyclohex-1-enyl






439




H




Pentafluorocyclopentadienyl






440




H




Pentachlorocyclopentadienyl






441




H




4-Dimethylaminophenyl




m.p.: 70-71° C.






442




H




4-Allyloxyphenyl




m.p.: 81-83° C.






443




H




Diphenylmethyl




m.p.: 66-68° C.






444




H




Dimethylbenzyl






1


H—NMR (CDCl


3


):









δ = 1.45s









3.78s, 4.03s, 5.00s,









7.17-7.41m






















TABLE VII







































No.




R


8




n






Data
















1




H




m.p. 156-158° C.






2




3-Fluoro






3




4-Fluoro






4




3-Chloro






5




4-Chloro






6




3-Bromo






7




4-Bromo






8




3-Iodo






9




4-Iodo






10




3,4-Dichloro






11




3,5-Dichloro






12




3,6-Dichloro






13




4,5-Dichloro






14




3,4,5-Trichloro






15




3,4,6-Trichloro






16




3,4,5,6-Tetrachloro






17




3,4,5,6-Tetrafluoro






18




3,4,5,6-Tetrabromo






19




3,5-Difluoro






20




3,5-Dibromo






21




3-Methyl






22




4-Methyl






23




3-Ethyl






24




4-Ethyl






25




3-iso-Propyl






26




4-iso-Propyl






27




3-tert.-Butyl






28




4-tert.-Butyl






29




3,4-Dimethyl






30




3,5-Dimethyl






31




3,6-Dimethyl






32




4,5-Dimethyl






33




3,4,5-Trimethyl






34




3,4,6-Trimethyl






35




3,4,5,6-Tetramethyl






36




3-Nitro






37




4-Nitro






38




3,5-Dinitro






39




3-Cyano






40




4-Cyano






41




3-Methoxy






42




4-Methoxy






43




3-tert.-Butoxy






44




4-tert.-Butoxy






45




3-Trifluoromethyl






46




4-Trifluoromethyl






47




3-Chloromethyl






48




4-Chloromethyl






49




3-Trifluoromethoxy






50




4-Trifluoromethoxy






51




3-Benzyloxy






52




4-Benzyloxy






53




4,5-Dibenzyloxy






54




3-Phenoxy






55




4-Phenoxy






56




3-Phenyl






57




4-Phenyl






58




3-Pyrid-2′-yl






59




4-Pyrid-2′-yl






60




3-Pyrid-2′-yloxy






61




4-Pyrid-2′-yloxy






















TABLE VIII







































No.




R


8




n






Data
















1




H




m.p. 152-155° C.






2




3-Fluoro






3




4-Fluoro






4




3-Chloro






5




4-Chloro






6




3-Bromo






7




4-Bromo






8




3-Iodo






9




4-Iodo






10




3,4-Dichloro






11




3,5-Dichloro






12




3,6-Dichloro






13




4,5-Dichloro






14




3,4,5-Trichloro






15




3,4,6-Trichloro






16




3,4,5,6-Tetrachloro






17




3,4,5,6-Tetrafluoro






18




3,4,5,6-Tetrabromo






19




3,5-Difluoro






20




3,5-Dibromo






21




3-Methyl






22




4-Methyl






23




3-Ethyl






24




4-Ethyl






25




3-iso-Propyl






26




4-iso-Propyl






27




3-tert-Butyl






28




4-tert-Butyl






29




3,4-Dimethyl






30




3,5-Dimethyl






31




3,6-Dimethyl






32




4,5-Dimethyl






33




3,4,5-Trimethyl






34




3,4,6-Trimethyl






35




3,4,5,6-Tetramethyl






36




3-Nitro






37




4-Nitro






38




3,5-Dinitro






39




3-Cyano






40




4-Cyano






41




3-Methoxy






42




4-Methoxy






43




3-tert.Butoxy






44




4-tert.Butoxy






45




3-Trifluoromethyl






46




4-Trifluoromethyl






47




3-Chloromethyl






48




4-Chloromethyl






49




3-Trifluoromethoxy






50




4-Trifluoromethoxy






51




3-Benzyloxy






52




4-Benzyloxy






53




4,5-Dibenzyloxy






54




3-Phenoxy






55




4-Phenoxy






56




3-Phenyl






57




4-Phenyl






58




3-Pyrid-2′-yl






59




4-Pyrid-2′-yl






60




3-Pyrid-2′-yloxy






61




4-Pyrid-2′-yloxy






















TABLE IX










































No.




X




Y




R


1






R


8






Data


















1




CH—SCH


3






O




CH


3






H






2




CH—SCH


3






NH




CH


3






H






3




CH—SCH


3






S




CH


3






H






4




CH


2






O




CH


3






H






5




CH


2






NH




CH


3






H






6




CH


2






S




CH


3






H






7




CH—CH


3






O




CH


3






H






8




CH—CH


3






NH




CH


3






H






9




CH—CH


3






S




CH


3






H






10




CH—CH


3






O




CH


3






Perchloro






11




CH—CH


3






NH




CH


3






Perchloro






12




CH—CH


3






S




CH


3






Perchloro






13




CH—OCH


3






NH




CH


3






H






14




CH—OCH


3






S




CH


3






H






15




CH—OCH


3






NH




CH


3






Perchloro






16




CH—OCH


3






S




CH


3






Perchloro






17




N—OCH


3






NH




CH


3






H






18




N—OCH


3






S




CH


3






H






19




N—OCH


3






NH




CH


3






Perchloro






20




N—OCH


3






S




CH


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 anonic 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-α-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 finely 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° and 280° 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-α-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel. By finely dispersing the mixture in 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° to 22° 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° to 22° 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° to 24° 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, Oendrolimus 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, Plathypena scarbra, Plutella xylostella, rseudoplusia 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, Sruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Oiabrotica 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, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sltona 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, oacus aleae, 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 Frankliniella fusca, Frankliniella 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, Oysdercus cingulatus, Oysdercus 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






Compound no.




in ppm




in %

























from Table I








49




100




80






36




100




80






43




1000




100






429




1000




100






38




40




100






39




100




100






45




1000




100






582




about 20




100






579




20




80






583




40




100






573




20




100






593




1000




80






592




40




100






704




about 20




100






705




40




100






from Table II






37




1000




100






39




1000




100






45




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 files 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




Mortality






from Table I




in ppm




in %

























49




0.1




80






36




1.0




80






37




0.1




100






582




0.1




80






593




0.1




60






705




0.1




100






706




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




Mortality






from Table I




in ppm




in %

























49




200




80






36




200




80






429




1000




80






16




400




80






582




400




100






593




1000




80






592




400




80






705




400




80






706




400




80














USE EXAMPLE 6




Action on Peronospora in Grapes




Leaves of potted vines of the “Müller 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° C. and then for 5 days in a greenhouse at from 20° to 30° 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%).



Claims
  • 1. O-benzyloxime ether of the formula I whereX is N—C1-C4alkoxy, Y is O or NR5, R1, R2 and R5 are H or C1-C4-alkyl, Z1 and Z2 are identical or different and each is H, halogen, methyl, methoxy or cyano, R3 and R4 are identical or different and each is hydrogen, cyano, straight-chain or branched C1-C10-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, arylthio-C1-C4-alkyl, C2-C6-alkenyl, C2-C5-haloalkenyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C4-alkylthio, benzylthio, C1-C4-alkylcarbonyl, substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, C1-C4-alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C1-C4-alkyl, substituted or unsubstituted aryl-C2-C4-alkenyl, substituted or unsubstituted aryloxy-C1-C4-alkyl, or substituted or unsubstituted arylthio-C1-C4-alkyl, N(R6)2, where the radicals R6 are identical or different and each is H, C1-C6-alkyl or substituted or unsubstituted phenyl, —CO—N(R7)2, where the radicals R7 are identical or different and each is H or C1-C4-alkyl, substituted or unsubstituted meaning, in addition to hydrogen, the radicals halogen, cyano, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C10-alkoximino-C1-C2-alkyl, aryl, aryloxy, benzyloxy, or C3-C6-cycloalkyl, or R3 and R4 together with the carbon atom to which they are attached form cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralyl, idanyl or fluorenyl, each of which may be substituted by the radicals stated above under substituted or unsubstituted, or R3 and R4 may be halogen; and “aryl”, alone or as part of another radical, is phenyl, naphthyl, or anthryl.
  • 2. O-Benzyloxime ethers of the formula III where the radicals R3 and R4 have the meanings given in claim 1.
  • 3. A compound of the formula I as set forth in claim 1, whereinX is NOCH3 or NOC2H5, Y is 0, R1 is C1-C4-alkyl, R2 is H or C1-C2-alkyl, R3 and R4 are identical or different and each is hydrogen, cyano, straight-chain or branched C1-C10-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C6-alkylthio-C1-C4-alkyl, arylthio-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C2-C4-haloalkenyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C1-C4-alkyl, or substituted or unsubstituted aryl-C2-C4-alkenyl, N(R6)2, where R6 is identical or different and each is H, C1-C6-alkyl, C3-C6-cycloalkyl or substituted or unsubstituted phenyl, CO—N(R7)2, where R7 is identical or different and each is H or C1-C4-alkyl; or R3 and R4 together with the carbon atom to which they are attached form cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralyl, indanyl, or fluorenyl, each of which may be substituted by the radicals given under substituted or unsubstituted, or R3 or R4 may be halogen; Z1 and Z2 are each hydrogen; and substituted or unsubstituted and aryl have the meanings given in claim 1.
  • 4. A fungicidal composition comprising in inert carrier and a fungicidally effective amount of an O-benzyloxime ether of the formula I according to claim 1.
  • 5. A process for combating fungi, wherein the fungi, or the materials, plants or seed threatened by fungus attack, or the soil, are treated with a fungicidally effective amount of a compound of the formula I according to claim 1.
  • 6. A compound of the formula I as set forth in claim 1, wherein R1 is methyl, R2 is H, R3 is CN, R4 is cyclopropyl, X is N—OCH3, Y is O, and Z1 and Z2 are hydrogen.
  • 7. A compound according to claim 1, wherein Y is NR5.
  • 8. A compound according to claim 710, wherein R1 is methyl, Z1, Z2, R2 and R5 are hydrogen, X is NOCH3, R3 is methyl, and R4 is 3,5-dichlorophenyl.
  • 9. O-benzyloxime ether of the formula I whereX is N—C1-C4-alkoxy, Y is O, R1 is C1-C4-alkyl, R2, Z1 and Z2 are H, R3 is hydrogen, methyl, ethyl, propyl or cyano, R4 is hydrogen, cyano, straight-chain or branched C1-C10-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, arylthio-C1-C4-alkyl, C2-C6-alkenyl, C2-C5-haloalkenyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C4-alkylthio, benzylthio, C1-C4-alkylcarbonyl, substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, C1-C4-alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl, aryl substituted by C1-C10-alkoximino-C1-C2-alkyl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C1-C4-alkyl, substituted or unsubstituted aryl-C2-C4-alkenyl, substituted or unsubstituted aryloxy-C1-C4-alkyl, or substituted or unsubstituted arylthio-C1-C4-alkyl, N(R6)2, where the radicals R6 are identical or different and each is H, C1-C6-alkyl or substituted or unsubstituted phenyl, —CO—N(R7)2, where the radicals R7 are identical or different and each is H or C1-C4-alkyl, substituted or unsubstituted meaning, in addition to hydrogen, the radicals halogen, cyano, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C10-alkoximino-C1-C2-alkyl, aryl, aryloxy, benzyloxy, or C3-C6-cycloalkyl, or R3 and R4 together with the carbon atom to which they are attached form cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralyl, indanyl or fluorenyl, each of which may be substituted by the radicals stated above under substituted or unsubstituted, or R3 or R4 may be halogen, and “aryl”, alone or as part of another radical, is phenyl, naphthyl, or anthryl.
  • 10. O-benzyloxime ether of the formula Iwhere X is N—C1-C4-alkoxy Y is NR5, R1, R2 and R5 are H or C1-C4-alkyl, Z1 and Z2 are identical or different and each is H, halogen, methyl, methoxy or cyano, R3 and R4 are identical or different and each is hydrogen, cyano, straight-chain or branched C1-C10-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, arylthio-C1-C4-alkyl, C2-C6-alkenyl, C2-C5-haloalkenyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C4-alkylthio, benzylthio, C1-C4-alkylcarbonyl substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, C1-C4-alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C1-C4-alkyl, substituted or unsubstituted aryl-C2-C4-alkenyl, substituted or unsubstituted aryloxy-C1-C4-alkyl, or substituted or unsubstituted arylthio-C1-C4-alkyl, N(R6)2, where the radicals R6 are identical or different and each is H, C1-C6-alkyl or substituted or unsubstituted phenyl, —CO—N(R7)2, where the radicals R7 are identical or different and each is H or C1-C4-alkyl, substituted or unsubstituted meaning, in addition to hydrogen, the radicals halogen, cyano, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C10-alkoximino-C1-C2-alkyl, aryl, aryloxy, benzyloxy, or C3-C6-cycloalkyl, or R3 and R4 together with the carbon atom to which they are attached form cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralyl, indanyl or fluorenyl, each of which may be substituted by the radicals stated above under substituted or unsubstituted or R3 or R4 may be halogen; and “aryl”, alone or as part of another radical, is phenyl, naphthyl, or anthryl.
  • 11. The O-benzyloxime ether of claim 10, wherein R2 is hydrogen.
  • 12. O-Benzyloxime ethers of the formula IIwhere X is N—C1-C4 alkoxy, R1 and R5 are H or C1-C4-alkyl, Z1 and Z2 are identical or different and each is H, halogen, methyl, methoxy or cyano, R3 is cyano, and R4 is substituted or unsubstituted phenyl or naphthyl, and the substituents on the phenyl or naphthyl are halogen, cyano, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C10-alkoximino-C1-C2-alkyl, aryl, aryloxy, benzyloxy, or C3-C6-cycloalkyl.
  • 13. A fungicidal composition comprising an inert carrier and a fungicidally effective amount of an O-benzyloxime ether of the formula Iaccording to claim 10.
  • 14. A process for combating fungi, wherein the fungi, or the materials, plants, or seed threatened by fungus attack or the soil, are treated with a fungicidally effective amount of a compound of the formula Iaccording to claim 10.
Priority Claims (2)
Number Date Country Kind
40 20 388 Jun 1990 DE
40 20 384 Jun 1990 DE
US Referenced Citations (2)
Number Name Date Kind
5221691 Clough Jun 1993 A
5238956 Clough Aug 1993 A
Foreign Referenced Citations (3)
Number Date Country
0253213 Jan 1988 EP
0370629 May 1990 EP
0414153 Feb 1991 EP
Divisions (1)
Number Date Country
Parent 07/722209 Jun 1991 US
Child 08/627377 US
Reissues (1)
Number Date Country
Parent 07/722209 Jun 1991 US
Child 08/627377 US