TREA

Phenylacetic acid derivatives, preparation thereof and intermediates therefor, and compositions containing them

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Information

  • Patent Grant
  • 6187812
  • Patent Number
    6,187,812
  • Date Filed
    Thursday, February 3, 2000
    24 years ago
  • Date Issued
    Tuesday, February 13, 2001
    23 years ago
Information
Abstract
Phenylacetic acid derivatives of the formula I where the substituents and the index have the following meanings:X is oxygen or sulfur;R is hydrogen or alkyl;R1 is hydrogen or alkyl;R2 is cyano, nitro, trifluoromethyl, halogen, alkyl or alkoxy;m is 0, 1 or 2, it being possible for the R2 radicals to be different if m is 2; R3 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylamino or dialkylamino;R4 is hydrogen, cyano, nitro, hydroxyl, amino, halogen,unsubstituted or substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, alkenyl, alkenyloxy, alkenylthio, alkenylamino, N-alkenyl-N-alkylamino, alkynyl, alkynyloxy, alkynylthio, alkynylamino, N-alkynyl-N-alkylamino;unsubstituted or substituted cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, N-cycloalkyl-N-alkylamino, cycloalkenyl, cycloalkenyloxy, cycloalkenylthio, cycloalkenylamino, N-cycloalkenyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-N-alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetaryl amino, N-hetaryl-N-alkylamino;R5 is hydrogen,unsubstituted or substituted alkyl, cycloalkyl, alkenyl, alkynyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl or alkylsulfonyl;unsubstituted or substituted aryl, arylcarbonyl, arylsulfonyl; hetaryl, hetarylcarbonyl or hetarylsulfonyl,and their salts, processes and intermediates for their preparation, and their use are described.
Description




The present invention relates to phenylacetic acid derivatives of the formula I











where the substituents and the index have the following meanings:




X is oxygen or sulfur;




R is hydrogen and or C


1


-C


4


-alkyl;




R


1


is hydrogen and or C


1


-C


4


-alkyl;




R


2


is cyano, nitro, trifluoromethyl, halogen, C


1


-C


4


-alkyl or C


1


-C


4


-alkoxy;




m is 0, 1 or 2, it being possible for the R


2


radicals to be different if m is 2;




R


3


is hydrogen, cyano, nitro, hydroxyl, amino, halogen,




C


1


-C


4


-alkyl, C


1


-C


4


-haloalkyl, C


1


-C


4


-alkoxy, C


1


-C


4


-haloalkoxy, C


1


-C


4


-alkylthio, C


1


-C


4


-alkylamino or di-C


1


-C


4


-alkylamino;




R


4


is hydrogen, cyano, nitro, hydroxyl, amino, halogen, C


1


-C


6


-alkyl, C


1


-C


6


-alkoxy, C


1


-C


6


-alkylthio, C


1


-C


6


-alkylamino, di-C


1


-C


6


-alkylamino, C


2


-C


6


-alkenyl, C


2


-C


6


-alkenyloxy, C


2


-C


6


-alkenylthio, C


2


-C


6


-alkenylamino, N-C


2


-C


6


-alkenyl-N-C


1


-C


6


-alkylamino, C


2


-C


6


-alkynyl, C


2


-C


6


-alkynyloxy, C


2


-C


6


-alkynylthio, C


2


-C


6


-alkynylamino, N-C


2


-C


6


-alkynyl-N-C


1


-C


6


-alkylamino, it being possible for the hydrocarbon radicals of these groups to be partly or completely halogenated or to carry one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C


1


-C


6


-alkylaminocarbonyl, di-C


1


-C


6


-alkylaminocarbonyl, C


1


-C


6


-alkylaminothiocarbonyl, di-C


1


-C


6


-alkylaminothiocarbonyl, C


1


-C


6


-alkylsulfonyl, C


1


-C


6


-alkylsulfoxyl, C


1


-C


6


-alkoxy, C


1


-C


6


-haloalkoxy, C


1


-C


6


-alkoxycarbonlyl, C


1


-C


6


-alkylthio, C


1


-C


6


-alkylamino, di-C


1


-C


6


-alkylamino, C


2


-C


6


-alkenyloxy, C


3


-C


6


-cycloalkyl, C


3


-C


6


-cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C


1


-C


4


-alkoxy, arylthio, aryl-C


1


-C


4


-alkylthio, hetaryl, hetaryloxy, hetaryl-C


1


-C


4


-alkoxy, hetarylthio, hetaryl-C


1


-C


4


-alkylthio, it being possible for the cyclic radicals in turn to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C


1


-C


6


-alkyl, C


1


-C


6


-haloalkyl, C


1


-C


6


-alkylsulfonyl, C


1


-C


6


-alkylsulfoxyl, C


3


C


6


-cycloalkyl, C


1


-C


6


-alkoxy, C


1


-C


6


-haloalkoxy, C


1


-C


6


-alkoxycarbonyl, C


1


-C


6


-alkylthio, C


1


-C


6


-alkylamino, di-C


1


-C


6


-alkylamino, C


1


-C


6


-alkylaminocarbonyl, di-C


1


-C


6


-alkylaminocarbonyl, C


1


-C


6


-alkylaminothiocarbonyl, di-C


1


-C


6


-alkylaminothiocarbonyl, C


2


-C


6


-alkenyl, C


2


-C


6


-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C(═NOR


6


)—A


n


—R


7


;




C


3


-C


6


-cycloalkyl, C


3


-C


6


-cycloalkoxy, C


3


-C


6


-cycloalkylthio, C


3


-C


6


-cycloalkylamino, N-C


3


-C


6


-cycloalkyl-N-C


1


-C


6


-alkylamino, C


3


-C


6


-cycloalkenyl, C


3


-C


6


-cycloalkenyloxy, C


3


-C


6


-cycloalkenylthio, C


3


-C


6


-cycloalkenylamino, N-C


3


-C


6


-cycloalkenyl-N-C


1


-C


6


-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-N-C


1


-C


6


-alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N-C


1


-C


6


-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino, N-hetaryl-N-C


1


-C


6


-alkylamino, it being possible for the cyclic radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C


1


-C


6


-alkyl, C


1


-C


6


-haloalkyl, C


1


-C


6


-alkylsulfonyl, C


1


-C


6


-alkylsulfoxyl, C


3


-C


6


-cycloalkyl, C


1


-C


6


-alkoxy, C


1


-C


6


-haloalkoxy, C


1


-C


6


-alkoxycarbonyl, C


1


-C


6


-alkylthio, C


1


-C


6


-alkylamino, di-C


1


-C


6


-alkylamino, C


1


-C


6


-alkylaminocarbonyl, di-C


1


-C


6


-alkylaminocarbonyl, C


1


-C


6


-alkylaminothiocarbonyl, di-C


1


-C


6


-alkylaminothiocarbonyl, C


2


-C


6


-alkenyl, C


2


-C


6


-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy;




R


5


is hydrogen, C


1


-C


10


-alkyl, C


3


-C


6


-cycloalkyl, C


2


-C


10


-alkenyl, C


2


-C


10


-alkynyl, C


1


-C


10


-alkylcarbonyl, C


2


-C


10


-alkenylcarbonyl, C


3


-C


10


-alkynylcarbonyl or C


1


-C


10


-alkylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C


1


-C


6


-alkyl, C


1


-C


6


-haloalkyl, C


1


-C


6


-alkylsulfonyl, C


1


-C


6


-alkylsulfoxyl, C


1


-C


6


-alkoxy, C


1


-C


6


-haloalkoxy, C


1


-C


6


-alkoxycarbonyl, C


1


-C


6


-alkylthio, C


1


-C


6


-alkylamino, di -C


1


-C


6


-alkylamino, C


1


-C


6


-alkylaminocarbonyl, di-C


1


-C


6


-alkylaminocarbonyl, C


1


-C


6


-alkylaminothiocarbonyl, di-C


1


-C


5


-alkylaminothiocarbonyl, C


2


-C


6


-alkenyl, C


2


-C


6


-alkenyloxy, C


3


-C


6


-cycloalkyl, C


3


-C


6


-cycloalkoxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the cyclic groups in turn to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C


1


-C


6


-alkyl, C


1


-C


6


-haloalkyl, C


1


-C


6


-alkylsulfonyl, C


1


-C


6


-alkylsulfoxyl, C


3


-C


6


-cycloalkyl, C


1


-C


6


-alkoxy, C


1


-C


6


-haloalkoxy, C


1


-C


6


-alkoxycarbonyl, C


1


-C


6


-alkylthio, C


1


-C


6


-alkylamino, di-C


1


-C


6


-alkyl amino, C


1


-C


6


-alkyl aminocarbonyl, di-C


1


-C


6


-alkylaminocarbonyl, C


1


-C


6


-alkylaminothiocarbonyl, di-C


1


-C


6


-alkylaminothiocarbonyl, C


2


-C


6


-alkenyl, C


2


-C


6


-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(═NOR


6


)—A


n


—R


7


;




aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C


1


-C


6


-alkyl, C


1


-C


6


-haloalkyl, C


1


-C


6


-alkylcarbonyl, C


1


-C


6


-alkylsulfonyl, C


1


-C


6


-alkylsulfoxyl, C


3


-C


6


-cycloalkyl, C


1


-C


6


-alkoxy, C


1


-C


6


-haloalkoxy, C


1


-C


6


-alkoxycarbonyl, C


1


-C


6


-alkylthio, C


1


-C


6


-alkylamino, di-C


1


-C


6


-alkylamino, C


1


-C


6


-alkylaminocarbonyl, di-C


1


-C


6


-alkylaminocarbonyl, C


1


-C


6


-alkylaminothiocarbonyl, di-C


1


-C


6


-alkylaminothiocarbonyl, C


2


-C


6


-alkenyl, C


2


-C


6


-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(═NOR


6


)—A


n


—R


7


;




where




A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C


1


-C


6


-alkyl;




n is 0 or 1;




R


6


is hydrogen or C


1


-C


6


-alkyl and




R


7


is hydrogen or C


1


-C


6


-alkyl,




and their salts.




The invention additionally relates to processes and intermediates for preparing these compounds and compositions containing them for controlling animal pests and harmful fungi.




Phenylacetic acid derivatives for pest control are disclosed in the literature (EP-A 398 692, EP-A 477 631, EP-A 513 580, EP-A 567 828, EP-A 528 682, EP-A 463 488, WO-A 92113,830).




It is an object of the present invention to provide novel compounds having improved action.




We have found that this object is achieved by the phenylacetic acid derivatives I defined at the outset. We have additionally found processes and intermediates for their preparation and compositions containing them for controlling animal pests and harmful fungi and their use within this context.




The compounds I are obtainable in various ways by processes known per se in the literature.




Fundamentally, it is insignificant in the synthesis of the compounds I whether the group


⊖


C(NOCH


3


)—CONRR


1


or the group —CH


2


ON═C(R


3


)—C(R


4


)NOR


5


is constructed first.




The construction of the group —C(NOCH


3


)—CONRR


1


is disclosed, for example, in the literature cited at the outset.




The manner of the synthesis of the —CH


2


ON—C(R


3


)═C(R


4


)—NOR


3


side chain essentially depends on the nature of the substituents R


3


and R


4


.




1. In the case in which R


3


and R


4


are not halogen, the construction of the group —CH


2


ON═C(R


3


)—C(R


4


)—NOR


5


in general proceeds by reacting a benzyl derivative of the formula II with a hydroxyimine of the formula III.











L


1


in the formula II is a nucleophilically replaceable leaving group, eg. halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.




The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, eg. sodium hydride, potassium hydroxide, potassium carbonate or triethylamine according to the methods described in Houben-Weyl, Vol. E 14b, p. 370 ff and Houben-Weyl, Vol. 10/1, p. 1189 ff.




The hydroxyimine III required is obtained, for example, by reaction of a corresponding dihydroxyimine IV with a nucleophilically substituted reagent VI











L


2


in the formula VI is a nucleophilically replaceable leaving group, eg. halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.




The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, eg. potassium carbonate, potassium hydroxide, sodium hydride, pyridine or triethylamine according to the methods described in Houben-Weyl, Vol. E 14b, p. 307 ff, p. 370 ff and p. 385 ff; Houben-Weyl, Vol. 10/4, p. 55 ff, p. 180 ff and p. 217 ff: Houben-Weyl, Vol. E5, p. 760 ff.




1.1 Alternatively, the compounds I can also be obtained by converting the benzyl derivative II first to a corresponding benzyl oxime of the formula V using the dihydroxyimine IV, V then being reacted with the nucleophilically substituted reagent VI to give I.











The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, eg. potassium carbonate, potassium hydroxide, sodium hydride, pyridine or triethylamine according to the methods described in Houben-Weyl, Vol. 10/1, p. 1189 ff; Houben-Weyl, Vol. E 14b, p. 307 ff, p. 370 ff and p. 385 ff; Houben-Weyl, Vol. 10/4, p. 55 ff, p. 180 ff and p. 217 ff; Houben-Weyl, Vol. E5, P. 780 ff.




1.2 In a similar manner, it is also possible to prepare the required hydroxyimine of the formula III from a carbonyl-hydroxyimine VII by reaction with a hydroxylamine IXa or its salt IXb.











Q


⊖


in the formula IXb is the anion of an acid, in particular of an inorganic acid, eg. halide such as chloride.




The reaction is carried out in a manner known per se in an inert organic solvent according to the methods described in EP-A 513 580; Houben-Weyl, Volume 10/4, p. 73 ff; Houben-Weyl, Vol. E14b, p. 369 ff and p. 385 ff.




1.3 Alternatively, the compounds I can also be obtained by converting the benzyl derivative II first to a corresponding benzylketoxyimine of the formula VIII using the carbonylhydroxyimine VII, VIII then being reacted with the hydroxylamine IXa or its salt IXb to give I.











The reaction is carried out in a manner known per se in an inert organic solvent according to the methods described in Houben-Weyl, Vol. E14b, p. 369 ff; Houben-Weyl, Vol. 10/1, p. 1189 ff and Houben-Weyl, Vol. 10/4, p. 73 ff or EP-A 513 580.




1.4 Another possibility for preparing the compounds I is the reaction of the benzyl derivative II with N-hydroxyphthalimide and subsequent hydrazinolysis to the benzylhydroxylamine IIa and the further reaction of IIa with a carbonyl compound X.











The reaction is carried out in a manner known per se in an inert organic solvent according to the methods described in EP-A 463 488 and German Appl. No. 42 28 867.3.




The carbonyl compound X required is obtained, for example, by reaction of a corresponding hydroxyiminocarbonyl VIIa with a nucleophilically substituted reagent VI











or by reaction of a corresponding dicarbonyl XI with a hydroxylamine IXa or its salt IXb











The reactions are carried out in a manner known per se in an inert organic solvent according to the methods described in EP-A 513 580, Houben-Weyl, Vol. 10/4, p. 55 ff, p. 73 ff, p. 180 ff and p. 217 ff, Houben-Weyl, Vol. E14b, p. 307 ff and 369 ff, Houben-Weyl, Vol. E5, p. 780 ff.




1.5 Correspondingly, the compounds I can also be obtained by converting the benzylhydroxylamine IIa first to the corresponding benzyloxyimine of the formula V using the hydroxyiminocarbonyl VIIa, V then being reacted with the nucleophilically substituted reagent VI to give I as described above.











1.6 In a similar manner, the compounds I can also be prepared by converting the benzylhydroxylamine IIa first to the benzyloxyimine VIII using the dicarbonyl of the formula XI and then reacting VIII with the hydroxylamine IXa or its salt IXb to give I as described above.











2. Compounds in which R


3


and/or R


4


are a halogen atom are obtained by methods known per se from the corresponding precursors in which the radical concerned is a hydroxyl group (cf. Houben-Weyl, Vol. E5, p. 631; J. Org. Chem. 36 (1971), 233; J. Org. Chem. 57 (1992), 3245). Preferably, the corresponding reactions to give the halogen derivative are performed in stages I and VIII.




3. Compounds in which R


3


and/or R


4


are bonded to the structure via an O, S or N atom are obtained by methods known per se from the corresponding precursors in which the radical concerned is a halogen atom (cf. Houben-Weyl, Vol. E5, p. 826 ff and 1280 ff, J. Org. Chem. 36 (1971), 233, J. Org. Chem. 46 (1981), 3623). Preferably, the corresponding conversions of the halogen derivative are performed in stages I and VIII.




4. Compounds in which R


3


and/or R


4


are bonded to the structure via an oxygen atom are in some cases also obtained by methods known per se from the corresponding precursors in which the radical concerned is a hydroxyl group (cf. Houben-Weyl, Vol. E5, p. 826-829, Aust. J. Chem. 27 (1974), 1341-9). Preferably, the corresponding reactions to give the alkoxy derivatives are performed in stages I and VIII.




5. Compounds in which R


3


is not halogen are preferably obtained by first converting a compound X to the corresponding benzoic acid XIII according to the methods described in EP-A 493 711 using a lactone XII and converting XIII via the corresponding halides to the cyanocarbqxylic acids XIV, which are then converted by way of the Pinner reaction (Angew. Chem. 94 (1982), 1) to the α-keto esters XV. The corresponding carboxamides, which are subsequently converted to the compounds I, are obtained from the derivatives XV by amidation.











6. The compounds XVI in which R is hydrogen can also be obtained directly from the carbonyl halides by reaction with isocyanates and subsequent hydrolysis by modifying the process described in 5. (EP 547 825).











7. In another variant, compounds XVI are obtained by converting an ortho halogen compound, after metallation with oxalyl chloride, to the corresponding keto acid chloride, which is subsequently converted with an amine to the corresponding amide XVI (cf. J. Org. Chem. 46 (1981), 46, 212 ff; DE-A 40 42 280; Houben-Weyl, Vol. E5, p. 972 ff).











8. In another variant, the compounds I in which X is oxygen are obtained, starting from the keto esters XV, by first converting the keto function to the oxime ether and converting the oxime ether thus obtained to I using an appropriate amine (Houben-Weyl, Vol. E5, p. 941 ff).











9. The compounds I in which X is sulfur are obtained from the corresponding amides I by reaction with a sulfurizing reagent (eg. phosphorus sulfide or Zawesson's reagent; cf. Houben-Weyl, Vol. IX, 764 ff).











The compounds II are known (EP-A 477 631, EP-A 463 488) or can be prepared by the methods described there.




On account of their C═C and C═N double bonds, the compounds I can be obtained during preparation as E/Z isomer mixtures which can be separated into the individual compounds in a customary manner, eg. by crystallization or chromatography.




If isomer mixtures are obtained during the synthesis, in general, however, a separation is not absolutely necessary, as the individual isomers can in some cases be converted to one another during preparation for application or during application (eg. under the action of light, acid or base). Corresponding conversions can also take place after application, for example during the treatment of plants in the treated plant or in the harmful fungus or animal pest to be controlled.




With reference to the C═NOCH


3


double bond, the cis isomers of the compounds I are preferred with respect to their activity (configuration based on the —OCH


3


group in relation to the —CXNRR


1


group).




With reference to the —C(R


3


)═NOCH


2


— double bond, the Z isomers of the compounds I are preferred with respect to their activity (configuration based on the radical R


3


in relation to the —OCH


2


— group).




In the definitions of the compounds I given at the outset, collective terms were used which are generally representative of the following groups:




halogen: fluorine, chlorine, bromine and iodine;




alkyl: straight-chain or branched alkyl groups having 1 to 4, 6 or 10 carbon atoms, eg. C


1


-C


6


-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;




alkylamino: an amino group which carries a straight-chain or branched alkyl group having 1 to 6 carbon atoms as mentioned above;




dialkylamino: an amino group which carries two straight-chain or branched alkyl groups which are independent of one another and each have 1 to 6 carbon atoms as mentioned above;




alkylcarbonyl: straight-chain or branched alkyl groups having 1 to 10 carbon atoms, which are bonded to the structure via a carbonyl group (—CO—);




alkylsulfonyl: straight-chain or branched alkyl groups having 1 to 6 or 10 carbon atoms, which are bonded to the structure via a sulfonyl group (—S(═O)


2


—);




alkylsulfoxyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, which are bonded to the structure via a sulfoxyl group (—S(═O)—);




alkylaminocarbonyl: alkylamino groups having 1 to 6 carbon atoms as mentioned above, which are bonded to the structure via a carbonyl group (—CO—);




dialkylaminocarbonyl: dialkylamino groups in each case having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the structure via a carbonyl group (—CO—);




alkylaminothiocarbonyl: alkylamino groups having 1 to 6 carbon atoms as mentioned above, which are bonded to the structure via a thiocarbonyl group (—CS—);




dialkylaminothiocarbonyl: dialkylamino groups in each case having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the structure via a thiocarbonyl group (—CS—);




haloalkyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, it being possible for the hydrogen atoms in these groups to be partly or completely replaced by halogen atoms as mentioned above, eg. C


1


-C


2


-haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;




alkoxy: straight-chain or branched alkyl groups having 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the structure via an oxygen atom (—O—), eg. C


1


-C


6


-alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy;




alkoxyzarbonyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, which are bonded to the structure via an oxycarbonyl group (—OC(═O)—);




haloalkoxy: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, it being possible for the hydrogen atoms in these groups to be partly or completely replaced by halogen atoms as mentioned above, and these groups being bonded to the structure via an oxygen atom;




alkylthio: straight-chain or branched alkyl groups having 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the structure via a sulfur atom (—S—), eg. C


1


-C


6


-alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio;




cycloalkyl: monocyclic alkyl groups having 3 to 6 carbon ring members, eg. cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;




alkenyl; straight-chain or branched alkenyl groups having 2 to 6 or 10 carbon atoms and a double bond in any desired position, eg. C


2


-C


6


-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;




alkenyloxy: straight-chain or branched alkenyl groups having 2 to 6 carbon atoms and a double bond in any desired position, which are bonded to the structure via an oxygen atom (—O—);




alkenylcarbonyl: straight-chain or branched alkenyl groups having 2 to 10 carbon atoms and a double bond in any desired position, which are bonded to the structure via a carbonyl group (—CO—);




alkenylthio or alkenylamino: straight-chain or branched alkenyl groups having 2 to 6 carbon atoms and a double bond in any desired position, which are bonded to the structure (alkenylthio) via a sulfur atom or (alkenylamino) a nitrogen atom;




alkynyl: straight-chain or branched alkynyl groups having 2 to 10 carbon atoms and a triple bond in any desired position, eg. C


2


-C


6


-alkynyl such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;




alkynylcarbonyl: straight-chain or branched alkynyl groups having 3 to 10 carbon atoms and a triple bond in any desired position, which are bonded to the structure via a carbonyl group (—CO—);




alkynyloxy or alkynylthio and alkynylamino: straight-chain or branched alkynyl groups having 2 to 6 carbon atoms and a triple bond in any desired position, which are bonded to the structure (alkynyloxy) via an oxygen atom or (alkynylthio) via a sulfur atom or (alkynylamino) via a nitrogen atom;




cycloalkenyl or cycloalkenyloxy, cycloalkenylthio and cycloalkylamino [sic]: monocyclic alkenyl groups having 3 to 6 carbon ring members, which are bonded to the structure directly or (cycloalkenyloxy) via an oxygen atom or (cycloalkenylthio) a sulfur atom or (cycloalkenylamino) via a nitrogen atom, eg. cyclopropenyl, cyclobutenyl, cyclopentenyl or cyclohexenyl;




cycloalkoxy or cycloalkylthio and cycloalkylamino: monocyclic alkenyl groups having 3 to 6 carbon ring members, which are bonded to the structure (cycloalkoxy) via an oxygen atom or (cycloalkylthio) a sulfur atom or (cycloalkylamino) via a nitrogen atom, eg. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;




heterocyclyl or heterocyclyloxy, heterocyclylthio and heterocyclylamino: three- to six-membered, saturated or partly unsaturated mono- or polycyclic heterocycles, which contain one to three heteroatoms selected from a group consisting of oxygen, nitrogen and sulfur, and which are bonded to the structure directly or (heterocyclyloxy) via an oxygen atom or (heterocyclylthio) via a sulfur atom or (heterocyclylamino) via a nitrogen atom, such as eg. 2-tetrahydrofuranyl, oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazoldinyl [sic], 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrizolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,3-dihydrofur-4-yl, 2,3-dihydrofur-5-yl, 2,5-dihydrofur-2-yl, 2,5-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,3-dihydrothien-4-yl, 2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 2,3-dihydropyrrol-2-yl, 2,3-dihydropyrrol-3-yl, 2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydroisopyrazol-3-yl, 2,3-dihydroisopyrazol-4-yl, 2,3-dihydroisopyrazol-5-yl, 4,5-dihydroisopyrazol-3-yl, 4,5-dihydroisopyrazol-4-yl, 4,5-dihydroisopyrazol-5-yl, 2,5-dihydroisopyrazol-3-yl, 2,5-dihydroisopyrazol-4-yl, 2,5-dihydroisopyrazol-5-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrooxazol-3-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-3-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl, 2-morpholinyl, 3-morpholinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl, 1,3,5-tetrahydrotriazin-2-yl, 1,2,4-tetrahydrotriazin-3-yl, 1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl, 2-tetrahydropyranyl, 1,3-dioxolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl, 4H-3,1-benzothiazin-2-yl, 1,1-dioxo-2,3,4,5-tetrahydrothien-2-yl, 2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl, 1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl;




aryl or aryloxy, arylthio, arylcarbonyl and arylsulfonyl: aromatic mono- or polycyclic hydrocarbon radicals which are bonded to the structure directly or (aryloxy) via an oxygen atom (—O—) or (arylthio) a sulfur atom (—S—), (arylcarbonyl) via a carbonyl group (—CO—) or (arylsulfonyl) via a sulfonyl group (—SO


2


—), eg. phenyl, naphthyl and phenanthrenyl or phenoxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl and sulfonyl radicals;




arylamino: aromatic mono- or polycyclic hydrocarbon radicals which are bonded to the structure via a nitrogen atom;




hetaryl or hetaryloxy, hetarylthio, hetarylcarbonyl and hetarylsulfonyl: aromatic mono- or polycyclic radicals which, in addition to carbon ring members, additionally can contain one to four nitrogen atoms or one to three nitrogen atoms and an oxygen or a sulfur atom or an oxygen or a sulfur atom and which are bonded to the structure directly or (hetaryloxy) via an oxygen atom (—O—) or (hetarylthio) a sulfur atom (—S—), (hetarylcarbonyl) via a carbonyl group (—CO—) or (hetarylsulfonyl) via a sulfonyl group (—SO—), eg.




5-membered heteroaryl, containing one to three nitrogen atoms: 5-membered ring heteroaryl groups which, in addition to carbon atoms, can contain one to three nitrogen atoms as ring members, eg. 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-triazol-3-yl and 1,3,4-triazol-2-yl;




5-membered heteroaryl, containing one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom or an oxygen or a sulfur atom: 5-membered ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom or an oxygen or sulfur atom as ring members, eg. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl;




benzo-fused 5-membered heteroarylo containing one to three nitrogen atoms or one nitrogen atom and/or an oxygen or sulfur atom: 5-membered ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom or an oxygen or a sulfur atom as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group;




5-membered heteroaryl bonded via nitrogen, containing one to four nitrogen atoms, or benzo-fused 5-membered heteroaryl bonded via nitrogen, containing one to three nitrogen atoms: 5-membered ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group, these rings being bonded to the structure via one of the nitrogen ring members;




6-membered heteroaryl, containing one to three or one to four nitrogen atoms: 6-membered ring heteroaryl groups which, in addition to carbon atoms, can contain one to three or one to four nitrogen atoms as ring members, eg. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazinyl;




benzo-fused 6-membered heteroaryl, containing one to four nitrogen atoms: 6-membered ring heteroaryl groups in which two adjacent carbon ring members can be bridged by a buta-1,3-diene- 1,4-diyl group, eg. quinoline, isoquinoline, quinazoline and quinoxaline,




or the corresponding oxy, thio, carbonyl or sulfonyl groups;




hetarylamino: aromatic mono- or polycyclic radicals which, in addition to carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and an oxygen or a sulfur atom or an oxygen or a sulfur atom and which are bonded to the structure via a nitrogen atom.




The statement partly or completely halogenated is intended to express that in the groups characterized in this way the hydrogen atoms can be partly or completely replaced by identical or different halogen atoms as mentioned above.




With respect to their biological action, compounds of the formula I are preferred in which m is 0.




Equally preferred are compounds of the formula I in which R is hydrogen or methyl.




Equally preferred are compounds of the formula I in which R


1


is hydrogen or methyl.




Compounds of the formula I are particularly preferred in which R is hydrogen and R


1


is hydrogen or methyl.




Compounds of the formula I are particularly preferred in which R and R


1


are simultaneously hydrogen or methyl.




In addition, compounds I are preferred in which R


3


is hydrogen, hydroxyl, cyclopropyl, chlorine, methyl, methoxy, methylthio or phenyl.




Compounds I are additionally preferred in which R


3


is methyl.




In addition, compounds I are preferred in which R


3


is methoxy.




Compounds I are additionally preferred in which R


3


is hydroxyl.




In addition, compounds I are preferred in which R


3


is chlorine.




In addition, compounds I are preferred in which R


4


is hydrogen, hydroxyl, cyclopropyl, chlorine, methyl, ethyl, isopropyl, methoxy or methylthio.




Compounds I are additionally preferred in which R


4


is methyl.




In addition, compounds I are preferred in which R


4


is methoxy.




Compounds I are additionally preferred in which R


4


is hydroxyl.




In addition, compounds I are preferred in which R


4


is ethyl.




Compounds I are additionally preferred in which R


4


is isopropyl.




Compounds I are additionally preferred in which R


4


is cyclopropyl.




In addition, compounds I are preferred in which R


4


is unsubstituted or substituted aryl or hetaryl.




In addition, compounds I are preferred in which R


4


is unsubstituted or substituted pyridyl, pyrimidyl, pyrazinyl, pyridazinyl or triazinyl.




In addition, compounds I are preferred in which R


4


is unsubstituted or substituted furyl, thienyl or pyrrolyl.




In addition, compounds I are preferred in which R


4


is unsubstituted or substituted oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazolyl.




In addition, compounds I are preferred in which R


4


is unsubstituted or substituted oxdiazolyl, thiadiazolyl or triazolyl.




Compounds I are additionally preferred in which R


4


is phenyl, which is unsubstituted or carries one or two of the following groups: nitro, cyano, hydroxyl, amino, aminocarbonyl, aminothiocarbonyl, halogen, C


1


-C


4


-alkyl, C


1


-C


4


-haloalkyl, C


1


-C


4


-alkoxy, C


1


-C


4


-haloalkoxy, C


1


-C


4


-alkylamino, di-C


1


-C


4


-alkylamino, C


1


-C


4


-alkylsulfonyl, C


1


-C


4


-alkoxycarbonyl, C


1


-C


4


-alkylaminocarbonyl or di-C


1


-C


4


-alkylaminocarbonyl.




Compounds I are additionally preferred in which R


5


is hydrogen, C


1


-C


6


-alkyl, arylalkyl, hetarylalkyl, aryloxyalkyl, hetaryloxyalkyl, aryl or hetaryl.




In addition, compounds I are preferred in which R


5


is C


1


-C


6


-alkyl.




Compounds I are additionally preferred in which R


5


is methyl or ethyl.




In addition, compounds I are preferred in which R


5


is arylalkyl or hetarylalkyl.




Compounds I are additionally preferred in which R


5


is aryloxyalkyl or hetaryloxyalkyl.




Compounds I are additionally preferred in which R


5


is aryl or hetaryl.




In addition, compounds of the formula I are preferred in which X is O.




In addition, compounds of the formula I are preferred in which X is S.




The compounds I compiled in the following tables are particularly preferred with respect to their use.




Table 1




Compounds of the general formula I.1 in which (R


2


)


m


is hydrogen and the combination of the substituents R


3


, R


4


and R


5


for a compound in each case corresponds to one line of Table A











Table 2




Compounds of the general formula I.1 in which (R


2


)


m


is chlorine and the combination of the substituents R


3


, R


4


and R


5


for a compound in each case corresponds to one line of Table A.




Table 3




Compounds of the general formula I.2 in which (R


2


)


m


is hydrogen and the combination of the substituents R


3


, R


4


and R


5


for a compound in each case corresponds to one line of Table A.











Table 4




Compounds of the general formula I.2 in which (R


2


)


m


is chlorine and the combination of the substituents R


3


, R


4


and R


5


for a compound in each case corresponds to one line of Table A.




Table 5




Compounds of the general formula 1.3 in which (R


2


)


m


is hydrogen and the combination of the substituents R


3


, R


4


and R


5


for a compound in each case corresponds to one line of Table A.











Table 6




Compounds of the general formula I.3 in which (R


2


)


m


is chlorine and the combination of the substituents R


3


, R


4


and R


5


for a compound in each case corresponds to one line of Table A.




Table 7




Compounds of the general formula I.4 in which (R


2


)


m


is hydrogen and the combination of the substituents R


3


, R


4


and R


5


for a compound in each case corresponds to one line of Table A.











Table 8




Compounds of the general formula I.4 in which (R


2


)


m


is chlorine and the combination of the substituents R


3


, R


4


and R


5


for a compound in each case corresponds to one line of Table A.




Table 9




Compounds of the general formula I.5 in which (R


2


)


m


is hydrogen and the combination of the substituents R


3


, R


4


and R


5


for a compound in each case corresponds to one line of Table A.











Table 10




Compounds of the general formula I.5 in which (R


2


)


m


is chlorine and the combination of the substituents R


3


, R


4


and R


5


for a compound in each case corresponds to one line of Table A.




Table 11




Compounds of the general formula I.6 in which (R


2


)


m


is hydrogen and the combination of the substituents R


3


, R


4


and R


5


for a compound in each case corresponds to one line of Table A.











Table 12




Compounds of the general formula I.6 in which (R


2


)


m


is chlorine and the combination of the substituents R


3


, R


4


and R


5


for a compound in each case corresponds to one line of Table A.















TABLE A









No.




R


3






R


4






R


5













1




CH


3






CH


3






H






2




CH


3






CH


3






CH


3








3




CH


3






CH


3






C


2


H


5








4




CH


3






CH


3






n-C


3


H


7








5




CH


3






CH


3






i-C


3


H


7








6




CH


3






CH


3






Cyclopropyl






7




CH


3






CH


3






n-C


4


H


9








8




CH


3






CH


3






s-C


4


H


9








9




CH


3






CH


3






i-C


4


H


9








10




CH


3






CH


3






t-C


4


H


9








11




CH


3






CH


3






n-C


5


H


11








12




CH


3






CH


3






i-C


5


H


11








13




CH


3






CH


3






neo-C


5


H


11








14




CH


3






CH


3






Cyclopentyl






15




CH


3






CH


3






n-C


6


H


13








16




CH


3






CH


3






Cyclohexyl






17




CH


3






CH


3






n-C


9


H


17








18




CH


3






CH


3






CH


2


CH


2


Cl






19




CH


3






CH


3






(CH


2


)


4


Cl






20




CH


3






CH


3






CH


2


CN






21




CH


3






CH


3






CH


2


CH


2


CN






22




CH


3






CH


3






(CH


2


)


3


CN






23




CH


3






CH


3






(CH


2


)


4


CN






24




CH


3






CH


3






(CH


2


)


6


CN






25




CH


3






CH


3






Cyclohexylmethyl






26




CH


3






CH


3






2-Cyclohexyleth-1-yl






27




CH


3






CH


3






Cyclopropylmethyl






28




CH


3






CH


3






2-Cyclopropyleth-1-yl






29




CH


3






CH


3






2-Methoxyeth-1-yl






30




CH


3






CH


3






2-Ethoxyeth-1-yl






31




CH


3






CH


3






2-Isopropoxyeth-1-yl






32




CH


3






CH


3






3-Methoxyprop-1-yl






33




CH


3






CH


3






3-Ethoxyprop-1-yl






34




CH


3






CH


3






3-Isopropoxyprop-1-yl






35




CH


3






CH


3






4-Methoxybut-1-yl






36




CH


3






CH


3






4-Isopropoxybut-1-yl






37




CH


3






CH


3






Propen-3-yl






38




CH


3






CH


3






But-2-en-1-yl






39




CH


3






CH


3






3-Methylbut-2-en-1-yl






40




CH


3






CH


3






2-Vinyloxyeth-1-yl






41




CH


3






CH


3






Allyloxyeth-1-yl






42




CH


3






CH


3






2-Trifluoromethoxyeth-1-yl






43




CH


3






CH


3






3-Trifluoromethoxyprop-1-yl






44




CH


3






CH


3






4-Difluoromethoxybut-1-yl






45




CH


3






CH


3






Hydroxycarbonylmethyl






46




CH


3






CH


3






Methoxycarbonylmethyl






47




CH


3






CH


3






Aminocarbonylmethyl






48




CH


3






CH


3






N-Methylaminocarbonylmethyl






49




CH


3






CH


3






N,N-Dimethylaminocarbonyl-









methyl






50




CH


3






CH


3






2-Hydroxycarbonyleth-1-yl






51




CH


3






CH


3






2-Methoxycarbonyleth-1-yl






52




CH


3






CH


3






2-Aminocarbonyleth-1-yl






53




CH


3






CH


3






2-N-Methylaminocarbonyleth-1-yl






54




CH


3






CH


3






2-Dimethylaminocarbonyleth-1-yl






55




CH


3






CH


3






2-Aminoeth-1-yl






56




CH


3






CH


3






2-Aminoprop-1-yl






57




CH


3






CH


3






4-Aminobut-1-yl






58




CH


3






CH


3






3-Dimethylaminoprop-1-yl






59




CH


3






CH


3






4-Aminothiocarbonylbut-1-yl






60




CH


3






CH


3






2-Oxopropyl






61




CH


3






CH


3






Cyclohexyl






62




CH


3






CH


3






Cyclopropyl






63




CH


3






CH


3






Cyclopentyl






64




CH


3






CH


3






2-Methoxyiminoprop-1-yl






65




CH


3






CH


3






2-Methoxyiminoeth-1-yl






66




CH


3






CH


3






6-Aminocarbonylhex-1-yl






67




CH


3






CH


3






3-Aminothiocarbonylprop-1-yl






68




CH


3






CH


3






2-Aminothiocarbonyleth-1-yl






69




CH


3






CH


3






Aminothiocarbonylmethyl






70




CH


3






CH


3






4-(N,N-Dimethylamino)but-1-yl






71




CH


3






CH


3






2-(Methylthio)eth-1-yl






72




CH


3






CH


3






2-(Methylsulfonyl)eth-1-yl






73




CH


3






CH


3






4-(Methylthio)prop-1-yl






74




CH


3






CH


3






4-(Methylsulfonyl)prop-1-yl






75




CH


3






CH


3






Benyzl






76




CH


3






CH


3






2-F—C


6


H


4


—CH


2








77




CH


3






CH


3






3-F—C


6


H


4


—CH


2








78




CH


3






CH


3






4-F—C


6


H


4


—CH


2








79




CH


3






CH


3






2,3-F


2


—C


6


H


3


—CH


2








80




CH


3






CH


3






2,4-F


2


—C


6


H


3


—CH


2








81




CH


3






CH


3






2,5-F


2


—C


6


H


3


—CH


2








82




CH


3






CH


3






2,6-F


2


—C


6


H


3


—CH


2








83




CH


3






CH


3






3,4-F


2


—C


6


H


3


—CH


2








84




CH


3






CH


3






3,5-F


2


—C


6


H


3


—CH


2








85




CH


3






CH


3






2-Cl—C


6


H


4


—CH


2








86




CH


3






CH


3






3-Cl—C


6


H


4


—CH


2








87




CH


3






CH


3






4-Cl—C


6


H


4


—CH


2








88




CH


3






CH


3






2,3-Cl


2


—C


6


H


3


—CH


2








89




CH


3






CH


3






2,4-Cl


2


—C


6


H


3


—CH


2








90




CH


3






CH


3






2,5-Cl


2


—C


6


H


3


—CH


2








91




CH


3






CH


3






2,6-Cl


2


—C


6


H


3


—CH


2








92




CH


3






CH


3






3,4-Cl


2


—C


6


H


3


—CH


2








93




CH


3






CH


3






3,5-Cl


2


—C


6


H


3


—CH


2








94




CH


3






CH


3






2,3,4-Cl


3


—C


6


H


2


—CH


2








95




CH


3






CH


3






2,3,5-Cl


3


—C


6


H


2


—CH


2








96




CH


3






CH


3






2,3,6-Cl


3


—C


6


H


2


—CH


2








97




CH


3






CH


3






2,4,5-Cl


3


—C


6


H


2


—CH


2








98




CH


3






CH


3






2,4,6-Cl


3


—C


6


H


2


—CH


2








99




CH


3






CH


3






3,4,5-Cl


3


—C


6


H


2


—CH


2








100




CH


3






CH


3






2-Br—C


6


H


4


—CH


2








101




CH


3






CH


3






3-Br—C


6


H


4


—CH


2








102




CH


3






CH


3






4-Br—C


6


H


4


—CH


2








103




CH


3






CH


3






2,3-Br


2


—C


6


H


3


—CH


2








104




CH


3






CH


3






2,4-Br


2


—C


6


H


3


—CH


2








105




CH


3






CH


3






2,5-Br


2


—C


6


H


3


—CH


2








106




CH


3






CH


3






2,6-Br


2


—C


6


H


3


—CH


2








107




CH


3






CH


3






3,4-Br


2


—C


6


H


3


—CH


2








108




CH


3






CH


3






3,5-Br


2


—C


6


H


3


—CH


2








109




CH


3






CH


3






2-F, 3-Cl—C


6


H


3


—CH


2








110




CH


3






CH


3






2-F, 4-Cl—C


6


H


3


—CH


2








111




CH


3






CH


3






2-F, 5-Cl—C


6


H


3


—CH


2








112




CH


3






CH


3






2-F, 3-Br—C


6


H


3


—CH


2








113




CH


3






CH


3






2-F, 4-Br—C


6


H


3


—CH


2








114




CH


3






CH


3






2-F, 5-Br—C


6


H


3


—CH


2








115




CH


3






CH


3






2-Cl, 3-Br—C


6


H


3


—CH


2








116




CH


3






CH


3






2-Cl, 4-Br—C


6


H


3


—CH


2








117




CH


3






CH


3






2-Cl, 5-Br—C


6


H


3


—CH


2








118




CH


3






CH


3






3-F, 4-Cl—C


6


H


3


—CH


2








119




CH


3






CH


3






3-F, 5-Cl—C


6


H


3


—CH


2








120




CH


3






CH


3






3-F, 6-Cl—C


6


H


3


—CH


2








121




CH


3






CH


3






3-F, 4-Br—C


6


H


3


—CH


2








122




CH


3






CH


3






3-F, 5-Br—C


6


H


3


—CH


2








123




CH


3






CH


3






3-F, 6-Br—C


6


H


3


—CH


2








124




CH


3






CH


3






3-Cl, 4-Br—C


6


H


3


—CH


2








125




CH


3






CH


3






3-Cl, 5-Br—C


6


H


3


—CH


2








126




CH


3






CH


3






3-Cl, 6-Br—C


6


H


3


—CH


2








127




CH


3






CH


3






4-F, 5-Cl—C


6


H


3


—CH


2








128




CH


3






CH


3






4-F, 6-Cl—C


6


H


3


—CH


2








129




CH


3






CH


3






4-F, 5-Br—C


6


H


3


—CH


2








130




CH


3






CH


3






4-F, 6-Br—C


6


H


3


—CH


2








131




CH


3






CH


3






4-Cl, 5-Br—C


6


H


3


—CH


2








132




CH


3






CH


3






5-F, 6-Cl—C


6


H


3


—CH


2








133




CH


3






CH


3






5-F, 6-Br—C


6


H


3


—CH


2








134




CH


3






CH


3






5-Cl, 6-Br—C


6


H


3


—CH


2








135




CH


3






CH


3






3-Br, 4-Cl, 5-Br—C


6


H


2


—CH


2








136




CH


3






CH


3






2-CN—C


6


H


4


—CH


2








137




CH


3






CH


3






3-CN—C


6


H


4


—CH


2








138




CH


3






CH


3






4-CN—C


6


H


4


—CH


2








139




CH


3






CH


3






2-NO


2


—C


6


H


4


—CH


2








140




CH


3






CH


3






3-NO


2


—C


6


H


4


—CH


2








141




CH


3






CH


3






4-NO


2


—C


6


H


4


—CH


2








142




CH


3






CH


3






2-CH


3


—C


6


H


4


—CH


2








143




CH


3






CH


3






3-CH


3


—C


6


H


4


—CH


2








144




CH


3






CH


3






4-CH


3


—C


6


H


4


—CH


2








145




CH


3






CH


3






2,3-(CH


3


)


2


—C


6


H


3


—CH


2








146




CH


3






CH


3






2,4-(CH


3


)


2


—C


6


H


3


—CH


2








147




CH


3






CH


3






2,5-(CH


3


)


2


—C


6


H


3


—CH


2








148




CH


3






CH


3






2,6-(CH


3


)


2


—C


6


H


3


—CH


2








149




CH


3






CH


3






3,4-(CH


3


)


2


—C


6


H


3


—CH


2








150




CH


3






CH


3






3,5-(CH


3


)


2


—C


6


H


3


—CH


2








151




CH


3






CH


3






2-C


2


H


5


—C


6


H


4


—CH


2








152




CH


3






CH


3






3-C


2


H


5


—C


6


H


4


—CH


2








153




CH


3






CH


3






4-C


2


H


5


—C


6


H


4


—CH


2








154




CH


3






CH


3






2-i-C


3


H


7


—C


6


H


4


—CH


2








155




CH


3






CH


3






3-i-C


3


H


7


—C


6


H


4


—CH


2








156




CH


3






CH


3






4-i-C


3


H


7


—C


6


H


4


—CH


2








157




CH


3






CH


3






2-Cyclohexyl-C


6


H


4


—CH


2








158




CH


3






CH


3






3-Cyclohexyl-C


6


H


4


—CH


2








159




CH


3






CH


3






4-Cyclohexyl-C


6


H


4


—CH


2








160




CH


3






CH


3






2-Vinyl-C


6


H


4


—CH


2








161




CH


3






CH


3






3-Vinyl-C


6


H


4


—CH


2








162




CH


3






CH


3






4-Vinyl-C


6


H


4


—CH


2








163




CH


3






CH


3






2-Allyl-C


6


H


4


—CH


2








164




CH


3






CH


3






3-Allyl-C


6


H


4


—CH


2








165




CH


3






CH


3






4-Allyl-C


6


H


4


—CH


2








166




CH


3






CH


3






2-C


6


H


5


—C


6


H


4


—CH


2








167




CH


3






CH


3






3-C


6


H


5


—C


6


H


4


—CH


2








168




CH


3






CH


3






4-C


6


H


5


—C


6


H


4


—CH


2








169




CH


3






CH


3






3-CH


3


, 5-t-C


4


H


9


—C


6


H


3


—CH


2








170




CH


3






CH


3






2-OH—C


6


H


4


—CH


2








171




CH


3






CH


3






3-OH—C


6


H


4


—CH


2








172




CH


3






CH


3






4-OH—C


6


H


4


—CH


2








173




CH


3






CH


3






2-OCH


3


—C


6


H


4


—CH


2








174




CH


3






CH


3






3-OCH


3


—C


6


H


4


—CH


2








175




CH


3






CH


3






4-OCH


3


—C


6


H


4


—CH


2








176




CH


3






CH


3






2,3-(OCH


3


)


2


—C


6


H


3


—CH


2








177




CH


3






CH


3






2,4-(OCH


3


)


2


—C


6


H


3


—CH


2








178




CH


3






CH


3






2,5-(OCH


3


)


2


—C


6


H


3


—CH


2








179




CH


3






CH


3






3,4-(OCH


3


)


2


—C


6


H


3


—CH


2








180




CH


3






CH


3






3,5-(OCH


3


)


2


—C


6


H


3


—CH


2








181




CH


3






CH


3






3,4,5-(OCH


3


)


3


—C


6


H


2


—CH


2








182




CH


3






CH


3






2-OC


2


H


5


—C


6


H


4


—CH


2








183




CH


3






CH


3






3-OC


2


H


5


—C


6


H


4


—CH


2








184




CH


3






CH


3






4-OC


2


H


5


—C


6


H


4


—CH


2








185




CH


3






CH


3






2-O-(n-C


3


H


7


)—C


6


H


4


—CH


2








186




CH


3






CH


3






3-O-(n-C


3


H


7


)—C


6


H


4


—CH


2








187




CH


3






CH


3






4-O-(n-C


3


H


7


)—C


6


H


4


—CH


2








188




CH


3






CH


3






2-O-(i-C


3


H


7


)—C


6


H


4


—CH


2








189




CH


3






CH


3






3-O-(i-C


3


H


7


)—C


6


H


4


—CH


2








190




CH


3






CH


3






4-O-(i-C


3


H


7


)—C


6


H


4


—CH


2








191




CH


3






CH


3






4-O-(n-C


4


H


9


)—C


6


H


4


—CH


2








192




CH


3






CH


3






3-O-(t-C


4


H


9


)—C


6


H


4


—CH


2








193




CH


3






CH


3






4-O-(n-C


6


H


13


)—C


6


H


4


—CH


2








194




CH


3






CH


3






2-O-Allyl-C


6


H


4


—CH


2








195




CH


3






CH


3






3-O-Allyl-C


6


H


4


—CH


2








196




CH


3






CH


3






4-0-Allyl-C


6


H


4


—CH


2








197




CH


3






CH


3






2-CF


3


—C


6


H


4


—CH


2








198




CH


3






CH


3






3-CF


3


—C


6


H


4


—CH


2








199




CH


3






CH


3






4-CF


3


—C


6


H


4


—CH


2








200




CH


3






CH


3






2-Acetyl-C


6


H


4


—CH


2








201




CH


3






CH


3






3-Acetyl-C


6


H


4


—CH


2








202




CH


3






CH


3






4-Acetyl-C


6


H


4


—CH


2








203




CH


3






CH


3






2-Methoxycarbonyl-C


6


H


4


—CH


2








204




CH


3






CH


3






3-Methoxycarbonyl-C


6


H


4


—CH


2








205




CH


3






CH


3






4-Methoxycarbonyl-C


6


H


4


—CH


2








206




CH


3






CH


3






2-Aminocarbonyl-C


6


H


4


—CH


2








207




CH


3






CH


3






3-Aminocarbonyl-C


6


H


4


—CH


2








208




CH


3






CH


3






4-Aminocarbonyl-C


6


H


4


—CH


2








209




CH


3






CH


3






2-Dimethylaminocarbo-









nyl-C


6


H


4


—CH


2








210




CH


3






CH


3






3-Dimethylaminocarbo-









nyl-C


6


H


4


—CH


2








211




CH


3






CH


3






4-Dimethylaminocarbo-









nyl-C


6


H


4


—CH


2








212




CH


3






CH


3






2-(N-Methylaminocarbo-









nyl)-C


6


H


4


—CH


2








213




CH


3






CH


3






3-(N-Methylaminocarbo-









nyl)-C


6


H


4


—CH


2








214




CH


3






CH


3






4-(N-Methylaminocarbo-









nyl)-C


6


H


4


—CH


2








215




CH


3






CH


3






2-H


2


N—C


6


H


4


—CH


2








216




CH


3






CH


3






3-H


2


N—C


6


H


4


—CH


2








217




CH


3






CH


3






4-H


2


N—C


6


H


4


—CH


2








218




CH


3






CH


3






2-Aminothiocarbonyl-C


6


H


4


—CH


2








219




CH


3






CH


3






3-Aminothiocarbonyl-C


6


H


4


—CH


2








220




CH


3






CH


3






4-Aminothiocarbonyl-C


6


H


4


—CH


2








221




CH


3






CH


3






2-Methoxyiminomethyl-









C


6


H


4


—CH


2








222




CH


3






CH


3






3-Methoxyiminomethyl-









C


6


H


4


—CH


2








223




CH


3






CH


3






4-Methoxyiminomethyl-









C


6


H


4


—CH


2








224




CH


3






CH


3






2-Formyl-C


6


H


4


—CH


2








225




CH


3






CH


3






3-Formyl-C


6


H


4


—CH


2








226




CH


3






CH


3






4-Formyl-C


6


H


4


—CH


2








227




CH


3






CH


3






2-(1′-Methoxyiminoeth-









1′-yl)-C


6


H


4


—CH


2








228




CH


3






CH


3






3-(1′-Methoxyiminoeth-1′-









yl)-C


6


H


4


—CH


2








229




CH


3






CH


3






4-(1′-Methoxyiminoeth-1′-









yl)-C


6


H


4


—CH


2








230




CH


3






CH


3






2-SCH


3


—C


6


H


4


—CH


2








231




CH


3






CH


3






3-SCH


3


—C


6


H


4


—CH


2








232




CH


3






CH


3






4-SCH


3


—C


6


H


4


—CH


2








233




CH


3






CH


3






2-SO


2


CH


3


—C


6


H


4


—CH


2








234




CH


3






CH


3






3-SO


2


CH


3


—C


6


H


4


—CH


2








235




CH


3






CH


3






4-SO


2


CH


3


—C


6


H


4


—CH


2








236




CH


3






CH


3






2-OCF


3


—C


6


H


4


—CH


2








237




CH


3






CH


3






3-OCF


3


—C


6


H


4


—CH


2








238




CH


3






CH


3






4-OCF


3


—C


6


H


4


—CH


2








239




CH


3






CH


3






2-OCHF


2


—C


6


H


4


—CH


2








240




CH


3






CH


3






3-OCHF


2


—C


6


H


4


—CH


2








241




CH


3






CH


3






4-OCHF


2


—C


6


H


4


—CH


2








242




CH


3






CH


3






3-CF


3


, 4-OCF


3


—C


6


H


3


—CH


2








243




CH


3






CH


3






1-Naphthyl-CH


2








244




CH


3






CH


3






2-Naphthyl-CH


2








245




CH


3






CH


3






2-Phenoxyeth-1-yl






246




CH


3






CH


3






2-(2′-Chlorophenoxy)eth-1-yl






247




CH


3






CH


3






2-(3′-Chlorophenoxy)eth-1-yl






248




CH


3






CH


3






2-(4′-Chlorophenoxy)eth-1-yl






249




CH


3






CH


3






2-(3′,5′-Dichlorophenoxy)-









eth-1-yl






250




CH


3






CH


3






2-(2′-Cyanophenoxy)eth-1-yl






251




CH


3






CH


3






2-(3′-Cyanophenoxy)eth-1-yl






252




CH


3






CH


3






2-(4′-Cyanophenoxy)eth-1-yl






253




CH


3






CH


3






2-(2′-Methylphenoxy)eth-1-yl






254




CH


3






CH


3






2-(3′-Methylphenoxy)eth-1-yl






255




CH


3






CH


3






2-(4′-Methylphenoxy)eth-1-yl






256




CH


3






CH


3






2-(3′-t-Butylphenoxy)eth-1-yl






257




CH


3






CH


3






2-(4′-t-Butylphenoxy)eth-1-yl






258




CH


3






CH


3






2-(2′-Nitrophenoxy)eth-1-yl






259




CH


3






CH


3






2-(3′-Nitrophenoxy)eth-1-yl






260




CH


3






CH


3






2-(4′-Nitrophenoxy)eth-1-yl






261




CH


3






CH


3






2-(2′-Methoxyphenoxy)eth-1-yl






262




CH


3






CH


3






2-(3′-Methoxyphenoxy)eth-1-yl






263




CH


3






CH


3






2-(4′-Methoxyphenoxy)eth-1-yl






264




CH


3






CH


3






2-(2′-Trifluoromethylphen-









oxy)eth-1-yl






265




CH


3






CH


3






2-(3′-Trifluoromethylphen-









oxy)eth-1-yl






266




CH


3






CH


3






2-(4′-Trifluoromethylphen-









oxy)eth-1-yl






267




CH


3






CH


3






2-(2′-Acetylphenoxy)eth-1-yl






268




CH


3






CH


3






2-(3′-Acetylphenoxy)eth-1-yl






269




CH


3






CH


3






2-(4′-Acetylphenoxy)eth-1-yl






270




CH


3






CH


3






2-(2′-Methoxycarbonyl)eth-1-yl






271




CH


3






CH


3






2-(3′-Methoxycarbonyl)eth-1-yl






272




CH


3






CH


3






2-(4′-Methoxycarbonyl)eth-1-yl






273




CH


3






CH


3






2-(2′-Dimethylamino-









carbonyl)eth-1-yl






274




CH


3






CH


3






2-(3′-Dimethylamino-









carbonyl)eth-1-yl






275




CH


3






CH


3






2-(4′-Dimethylamino-









carbonyl)eth-1-yl






276




CH


3






CH


3






2-(2′-Aminothiocarbonyl)eth-1-yl






277




CH


3






CH


3






2-(3′-Aminothiocarbonyl)eth-1-yl






278




CH


3






CH


3






2-(4′-Aminothiocarbonyl)eth-1-yl






279




CH


3






CH


3






2-(2′-Methylsulfonyl)eth-1-yl






280




CH


3






CH


3






2-(3′-Methylsulfonyl)eth-1-yl






281




CH


3






CH


3






2-(4′-Methylsulfonyl)eth-1-yl






282




CH


3






CH


3






3-Phenoxyprop-1-yl






283




CH


3






CH


3






3-(2′-Chlorophenoxy)prop-1-yl






284




CH


3






CH


3






3-(3′-Chlorophenoxy)prop-1-yl






285




CH


3






CH


3






3-(4′-Chlorophenoxy)prop-1-yl






286




CH


3






CH


3






3-(3′,5′,Dichlorophenoxy)prop-1-yl






287




CH


3






CH


3






3-(2′-Cyanophenoxy)prop-1-yl






288




CH


3






CH


3






3-(3′-Cyanophenoxy)prop-1-yl






289




CH


3






CH


3






3-(4′-Cyanophenoxy)prop-1-yl






290




CH


3






CH


3






3-(2′-Methylphenoxy)prop-1-yl






291




CH


3






CH


3






3-(3′-Methylphenoxy)prop-1-yl






292




CH


3






CH


3






3-(4′-Methylphenoxy)prop-1-yl






293




CH


3






CH


3






3-(2′-Methoxyphenoxy)prop-1-yl






294




CH


3






CH


3






3-(3′-Methoxyphenoxy)prop-1-yl






295




CH


3






CH


3






3-(4′-Methoxyphenoxy)prop-1-yl






296




CH


3






CH


3






3-(2′-Trifluoromethyl-









phenoxy)prop-1-yl






297




CH


3






CH


3






3-(3′-Trifluoromethyl-









phenoxy)prop-1-yl






298




CH


3






CH


3






3-(4′-Trifluoromethyl-









phenoxy)prop-1-yl






299




CH


3






CH


3






4-Phenoxybut-1-yl






300




CH


3






CH


3






2-Phenyleth-1-yl






301




CH


3






CH


3






2-(2′-Chlorophenyl)eth-1-yl






302




CH


3






CH


3






2-(3′-Chlorophenyl)eth-1-yl






303




CH


3






CH


3






2-(4′-Chlorophenyl)eth-1-yl






304




CH


3






CH


3






2-(3′,5′-Dichlorophenyl)eth-1-yl






305




CH


3






CH


3






2-(2′-Cyanophenyl)eth-1-yl






306




CH


3






CH


3






2-(3′-Cyanophenyl)eth-1-yl






307




CH


3






CH


3






2-(4′-Cyanophenyl)eth-1-yl






308




CH


3






CH


3






2-(2′-Methylphenyl)eth-1-yl






309




CH


3






CH


3






2-(3′-Methylphenyl)eth-1-yl






310




CH


3






CH


3






2-(4′-Methylphenyl)eth-1-yl






311




CH


3






CH


3






2-(2′-Methoxyphenyl)eth-1-yl






312




CH


3






CH


3






2-(3′-Methoxyphenyl)eth-1-yl






313




CH


3






CH


3






2-(4′-Methoxyphenyl)eth-1-yl






314




CH


3






CH


3






2-(2′-Trifluoromethyl-









phenyl)eth-1-yl






315




CH


3






CH


3






2-(3′-Trifluoromethyl-









phenyl)eth-1-yl






316




CH


3






CH


3






2-(4′-Trifluoromethyl-









phenyl)eth-1-yl






317




CH


3






CH


3






3-Phenylprop-1-yl






318




CH


3






CH


3






3-(2′-Chlorophenyl)prop-1-yl






319




CH


3






CH


3






3-(3′-Chlorophenyl)prop-1yl






320




CH


3






CH


3






3-(4′-Chlorophenyl)prop-1-yl






321




CH


3






CH


3






3-(2′-Cyanophenyl)prop-1-yl






322




CH


3






CH


3






3-(3′-Cyanophenyl)prop-1-yl






323




CH


3






CH


3






3-(4′-Cyanophenyl)prop-1-yl






324




CH


3






CH


3






3-(2′-Trifluoromethyl-









phenyl)prop-1-yl






325




CH


3






CH


3






4-Phenylbut-1-yl






326




CH


3






CH


3






4-(4′-Chlorophenyl)but-1-yl






327




CH


3






CH


3






6-(4′-Chlorophenyl)hex-1-yl






328




CH


3






CH


3






2-Pyridylmethyl






329




CH


3






CH


3






3-Pyridylmethyl






330




CH


3






CH


3






4-Pyridylmethyl






331




CH


3






CH


3






4-Chloropyridin-2-ylmethyl






332




CH


3






CH


3






5-Chloropyridin-2-ylmethyl






333




CH


3






CH


3






6-Chloropyridin-2-ylmethyl






334




CH


3






CH


3






5-Chloropyridin-3-ylmethyl






335




CH


3






CH


3






6-Chloropyridin-3-ylmethyl






336




CH


3






CH


3






2-Chloropyridin-4-ylmethyl






337




CH


3






CH


3






2-Pyrimidinylmethyl






338




CH


3






CH


3






4-Chloropyrimidin-2-yl-methyl






339




CH


3






CH


3






5-Chloropyrimidin-2-yl-methyl






340




CH


3






CH


3






2-Chloropyrimidin-4-yl-methyl






341




CH


3






CH


3






6-Chloropyrimidin-4-yl-methyl






342




CH


3






CH


3






2-Chloropyrimidin-5-yl-methyl






343




CH


3






CH


3






4-Pyridazinylmethyl






344




CH


3






CH


3






2-Pyrazinylmethyl






345




CH


3






CH


3






5-Chloropyrazin-2-ylmethyl






346




CH


3






CH


3






6-Chloropyrazin-2-ylmethyl






347




CH


3






CH


3






3-Pyridazinylmethyl






348




CH


3






CH


3






6-Chloropyridazin-3-yl-methyl






349




CH


3






CH


3






1,3,5-Triazinylmethyl






350




CH


3






CH


3






2-Furylmethyl






351




CH


3






CH


3






3-Furylmethyl






352




CH


3






CH


3






4-Bromofur-2-ylmethyl






353




CH


3






CH


3






5-Chlorofur-2-ylmethyl






354




CH


3






CH


3






2-Thienylmethyl






355




CH


3






CH


3






3-Thienylmethyl






356




CH


3






CH


3






5-Methylthien-3-ylmethyl






357




CH


3






CH


3






5-Chlorothien-2-ylmethyl






358




CH


3






CH


3






2-Chlorothien-4-ylmethyl






359




CH


3






CH


3






2-Pyrrolylmethyl






360




CH


3






CH


3






3-Pyrrolylmethyl






361




CH


3






CH


3






2-Oxazolylmethyl






362




CH


3






CH


3






4-Methyloxazol-2-ylmethyl






363




CH


3






CH


3






5-Methyloxazol-2-ylmethyl






364




CH


3






CH


3






4-Chlorooxazol-2-ylmethyl






365




CH


3






CH


3






5-Chlorooxazol-2-ylmethyl






366




CH


3






CH


3






4-Oxazolylmethyl






367




CH


3






CH


3






2-Methyloxazol-4-ylmethyl






368




CH


3






CH


3






5-Methyloxazol-4-ylmethyl






369




CH


3






CH


3






2-Chlorooxazol-4-ylmethyl






370




CH


3






CH


3






5-Chlorooxazol-4-ylmethyl






371




CH


3






CH


3






5-Oxazolylmethyl






372




CH


3






CH


3






2-Methyloxazol-5-ylmethyl






373




CH


3






CH


3






4-Methyloxazol-5-ylmethyl






374




CH


3






CH


3






2-Chlorooxazol-5-ylmethyl






375




CH


3






CH


3






4-Chlorooxazol-5-ylmethyl






376




CH


3






CH


3






2-Thiazolylmethyl






377




CH


3






CH


3






4-Methylthiazol-2-ylmethyl






378




CH


3






CH


3






5-Methylthiazol-2-ylmethyl






379




CH


3






CH


3






4-Chlorothiazol-2-ylmethyl






380




CH


3






CH


3






5-Chlorothiazol-2-ylmethyl






381




CH


3






CH


3






4-Thiazolylmethyl






382




CH


3






CH


3






2-Methylthiazol-4-ylmethyl






383




CH


3






CH


3






5-Methylthiazol-4-ylmethyl






384




CH


3






CH


3






2-Chlorothiazol-4-ylmethyl






385




CH


3






CH


3






5-Chlorothiazol-4-ylmethyl






386




CH


3






CH


3






5-Thiazolylmethyl






387




CH


3






CH


3






2-Methylthiazol-5-ylmethyl






388




CH


3






CH


3






4-Methylthiazol-5-ylmethyl






389




CH


3






CH


3






2-Chlorothiazol-5-ylmethyl






390




CH


3






CH


3






4-Chlorothiazol-5-ylmethyl






391




CH


3






CH


3






3-Isoxazolylmethyl






392




CH


3






CH


3






4-Methylisoxazol-3-ylmethyl






393




CH


3






CH


3






5-Methylisoxazol-3-ylmethyl






394




CH


3






CH


3






4-Chloroisoxazol-3-ylmethyl






395




CH


3






CH


3






5-Chloroisoxazol-3-ylmethyl






396




CH


3






CH


3






4-Isoxazolylmethyl






397




CH


3






CH


3






3-Methylisoxazol-4-ylmethyl






398




CH


3






CH


3






5-Methylisoxazol-4-ylmethyl






399




CH


3






CH


3






3-Chloroisoxazol-4-ylmethyl






400




CH


3






CH


3






5-Chloroisoxazol-4-ylmethyl






401




CH


3






CH


3






5-Isoxazolylmethyl






402




CH


3






CH


3






3-Methylisoxazol-5-ylmethyl






403




CH


3






CH


3






4-Methylisoxazol-5-ylmethyl






404




CH


3






CH


3






3-Chloroisoxazol-5-ylmethyl






405




CH


3






CH


3






4-Chloroisoxazol-5-ylmethyl






406




CH


3






CH


3






3-Isothiazolylmethyl






407




CH


3






CH


3






4-Methylisothiazol-3-yl-methyl






408




CH


3






CH


3






5-Methylisothiazol-3-yl-methyl






409




CH


3






CH


3






4-Chloroisothiazol-3-yl-methyl






410




CH


3






CH


3






5-Chloroisothiazol-3-yl-methyl






411




CH


3






CH


3






4-Isothiazolylmethyl






412




CH


3






CH


3






3-Methylisothiazol-4-yl-methyl






413




CH


3






CH


3






5-Methylisothiazol-4-yl-methyl






414




CH


3






CH


3






3-Chloroisothiazol-4-yl-methyl






415




CH


3






CH


3






5-Chloroisothiazol-4-yl-methyl






416




CH


3






CH


3






5-Isothiazolylmethyl






417




CH


3






CH


3






3-Methylisothiazol-5-yl-methyl






418




CH


3






CH


3






4-Methylisothiazol-5-yl-methyl






419




CH


3






CH


3






3-Chloroisothiazol-5-yl-methyl






420




CH


3






CH


3






4-Chloroisothiazol-5-yl-methyl






421




CH


3






CH


3






4-Imidazolylmethyl






422




CH


3






CH


3






1-Phenylpyrazol-3-ylmethyl






423




CH


3






CH


3






1-Methylimidazol-4-ylmethyl






424




CH


3






CH


3






1-Phenyl-1,2,4-triazol-3-ylmethyl






425




CH


3






CH


3






1,2,4-Oxadiazol-3-ylmethyl






426




CH


3






CH


3






5-Chloro-1,2,4-oxadiazol-3-









ylmethyl






427




CH


3






CH


3






5-Methyl-1,2,4-oxadiazol-3-









ylmethyl






428




CH


3






CH


3






5-Trifluoromethyl-1,2,4-









oxadiazol-3-ylmethyl






429




CH


3






CH


3






1,3,4-Oxadiazol-2-ylmethyl






430




CH


3






CH


3






5-Chloro-1,3,4-oxadiazol-2-









ylmethyl






431




CH


3






CH


3






5-Methyl-1,3,4-oxadiazol-2-









ylmethyl






432




CH


3






CH


3






5-Methoxy-1,3,4-oxadiazol-2-









ylmethyl






433




CH


3






CH


3






1,2,4-Thiadiazol-3-ylmethyl






434




CH


3






CH


3






5-Chloro-1,2,4-thiadiazol-3-









ylmethyl






435




CH


3






CH


3






5-Methyl-1,2,4-thiadiazol-3-









ylmethyl






436




CH


3






CH


3






1,3,4-Thiadiazol-2-ylmethyl






437




CH


3






CH


3






5-Chloro-1,3,4-thiadiazol-2-









ylmethyl






438




CH


3






CH


3






5-Methyl-1,3,4-thiadiazol-2-









ylmethyl






439




CH


3






CH


3






5-Cyano-1,3,4-thiadiazol-2-









ylmethyl






440




CH


3






CH


3






2-(2′-Pyridinyloxy)eth-1-yl






441




CH


3






CH


3






2-(3′-Pyridinyloxy)eth-1-yl






442




CH


3






CH


3






2-(4′-Pyridinyloxy)eth-1-yl






443




CH


3






CH


3






2-(2′-Pyrimidinyloxy)eth-1-yl






444




CH


3






CH


3






2-(4′-Pyrimidinyloxy)eth-1-yl






445




CH


3






CH


3






2-(5′-Pyrimidinyloxy)eth-1-yl






446




CH


3






CH


3






2-(2′-Pyrazinyloxy)eth-1-yl






447




CH


3






CH


3






2-(2′-Pyridazinyloxy)eth-1-yl






448




CH


3






CH


3






2-(3′-Pyridazinyloxy)eth-1-yl






449




CH


3






CH


3






2-(1′,3′,5′-Triazin-









yloxy)eth-1-yl






450




CH


3






CH


3






2-(5′-Methylisoxazol-3′-yl-









oxy)eth-1-yl






451




CH


3






CH


3






2-(5′-Chloroisoxazoi-3′-yl-









oxy)eth-1-yl






452




CH


3






CH


3






2-(2′-Methoxythiazol-4′-yl-









oxy)eth-1-yl






453




CH


3






CH


3






2-(4′-Chlorooxazol-2′-yl-









oxy)eth-1-yl






454




CH


3






CH


3






2-(1′-Phenyl-1′H-1′,2′,4′-









triazol-3′-yloxy)eth-1-yl






455




CH


3






CH


3






2-(1′-Phenylpyrazol-3′-yl-









oxy)eth-1-yl






456




CH


3






CH


3






C


6


H


5








457




CH


3






CH


3






2-Cl—C


6


H


4








458




CH


3






CH


3






3-Cl—C


6


H


4








459




CH


3






CH


3






4-Cl—C


6


H


4








460




CH


3






CH


3






2,3-Cl


2


—C


6


H


3








461




CH


3






CH


3






2,4-Cl


2


—C


6


H


3








462




CH


3






CH


3






2,5-Cl


2


—C


6


H


3








463




CH


3






CH


3






3,4-Cl


2


—C


6


H


3








464




CH


3






CH


3






3,5-Cl


2


—C


6


H


3








465




CH


3






CH


3






4-CN—C


6


H


4








466




CH


3






CH


3






2-NO


2


—C


6


H


4








467




CH


3






CH


3






3-NO


2


—C


6


H


4








468




CH


3






CH


3






4-NO


2


—C


6


H


4








469




CH


3






CH


3






2,4-(NO


2


)


2


—C


6


H


3








470




CH


3






CH


3






2-CH


3


—C


6


H


4








471




CH


3






CH


3






3-CH


3


—C


6


H


4








472




CH


3






CH


3






4-CH


3


—C


6


H


4








473




CH


3






CH


3






2,3-(CH


3


)


2


—C


6


H


3








474




CH


3






CH


3






2,4-(CH


3


)


2


—C


6


H


3








475




CH


3






CH


3






2,5-(CH


3


)


2


—C


6


H


3








476




CH


3






CH


3






2,6-(CH


3


)


2


—C


6


H


3








477




CH


3






CH


3






2-C


6


H


5


—C


6


H


4








478




CH


3






CH


3






3-C


6


H


5


—C


6


H


4








479




CH


3






CH


3






4-C


6


H


5


—C


6


H


4








480




CH


3






CH


3






3-OCH


3


—C


6


H


4








481




CH


3






CH


3






4-OCH


3


—C


6


H


4








482




CH


3






CH


3






3-Acetyl-C


6


H


4








483




CH


3






CH


3






4-Acetyl-C


6


H


4








484




CH


3






CH


3






3-Methoxycarbonyl-C


6


H


4








485




CH


3






CH


3






4-Methoxycarbonyl-C


6


H


4








486




CH


3






CH


3






3-CF


3


—C


6


H


4








487




CH


3






CH


3






4-CF


3


—C


6


H


4








488




CH


3






CH


3






2-Naphthyl






489




CH


3






CH


3






6-Chloropyridazin-3-yl






490




CH


3






CH


3






5-Chloropyrazin-2-yl






491




CH


3






CH


3






Quinolin-2-yl






492




CH


3






CH


3






2,5-Dimethylpyrazin-3-yl






493




CH


3






CH


3






Pyrazin-2-yl






494




CH


3






CH


3






3-Chloropyrid-2-yl






495




CH


3






CH


3






6-Chloropyrid-2-yl






496




CH


3






CH


3






4-Trifluoromethy [sic],









6-Chloropyrid-2-yl






497




CH


3






CH


3






4-Trifluoromethylpyrid-2-yl






498




CH


3






CH


3






6-Trifluoromethylpyrid-2-yl






499




CH


3






CH


3






6-Methoxypyrid-2-yl






500




CH


3






CH


3






5-Chloropyrid-2-yl






501




CH


3






CH


3






Pyrid-2-yl






502




CH


3






CH


3






Benzothiazol-2-yl






503




CH


3






CH


3






7-Chloroquinolin-4-yl






504




CH


3






CH


3






3-Nitropyrid-2-yl






505




CH


3






CH


3






Pyrrol-3-yl






506




CH


3






CH


3






Pyrrol-2-yl






507




CH


3






CH


3






2,6-Dioctylpyrid-4-yl






508




CH


3






CH


3






5-Nitropyrid-2-yl






509




CH


3






CH


3






Pyrid-4-yl






510




CH


3






CH


3






Pyrid-3-yl






511




CH


3






CH


3






Pyrimidin-2-yl






512




CH


3






CH


3






Pyrimidin-4-yl






513




CH


3






CH


3






Quinazolin-4-yl






514




CH


3






CH


3






6-Chloropyrimidin-4-yl






515




CH


3






CH


3






6-Methoxypyrimidin-4-yl






516




CH


3






CH


3






2,5,6-Trichloropyrimidin-4-yl






517




CH


3






CH


3






2,6-Dimethylpyrimidin-4-yl






518




CH


3






CH


3






2-Methyl, 6-Chloropyrimidin-4-yl






519




CH


3






CH


3






2-Methyl, 6-Ethoxypyrimidin-4-yl






520




CH


3






CH


3






4,5,6-Trichloropyrimidin-2-yl






521




CH


3






CH


3






4,6-Dimethoxypyrimidin-2-yl






522




CH


3






CH


3






4,6-Dimethylpyrimidin-2-yl






523




CH


3






CH


3






4,6-Dichloropyrimidin-2-yl






524




CH


3






CH


3






4-Methyl, 6-methoxypyrimidin-2-yl






525




CH


3






CH


3






4-Chloro, 6-methoxypyrimidin-2-yl






526




CH


3






CH


3






6-Chloroquinoxalin-2-yl






527




CH


3






CH


3






3,6-Dichloro-1,2,4-triazin-5-yl






528




CH


3






CH


3






4-Methoxy-1,3,5-triazin-2-yl






529




CH


3






CH


3






4-Ethoxy-1,3,5-triazin-2-yl






530




CH


3






CH


3






4,6-Dichloro-1,3,5-triazin-2-yl






531




CH


3






CH


3






4-Ethoxy,









6-Chloro-1,3,5-triazin-2-yl






532




CH


3






CH


3






Isoxazol-3-yl






533




CH


3






CH


3






Thien-2-yl






534




CH


3






CH


3






Fur-2-yl






535




CH


3






CH


3






Thiatriazol-5-yl






536




CH


3






CH


3






(E)-1-Chloropropen-3-yl






537




CH


3






CH


3






(E)-4-(4′-Chlorophenyl)but-









2-en-1-yl






538




CH


3






CH


3






Propyn-3-yl






539




CH


3






CH


3






Methylcarbonyl






540




CH


3






CH


3






Ethylcarbonyl






541




CH


3






CH


3






n-Propylcarbonyl






542




CH


3






CH


3






i-Propylcarbonyl






543




CH


3






CH


3






n-Butylcarbonyl






544




CH


3






CH


3






s-Butylcarbonyl






545




CH


3






CH


3






i-Butylcarbonyl






546




CH


3






CH


3






t-Butylcarbonyl






547




CH


3






CH


3






n-Pentylcarbonyl






548




CH


3






CH


3






i-Pentylcarbonyl






549




CH


3






CH


3






neo-Pentylcarbonyl






550




CH


3






CH


3






n-Hexylcarbonyl






551




CH


3






CH


3






n-Octylcarbonyl






552




CH


3






CH


3






1-Propenylcarbonyl






553




CH


3






CH


3






2-Penten-1-yl-carbonyl






554




CH


3






CH


3






2,5-Heptadien-1-yl-carbonyl






555




CH


3






CH


3






Benzoyl






556




CH


3






CH


3






2-Chlorobenzoyl






557




CH


3






CH


3






3-Chlorobenzoyl






558




CH


3






CH


3






4-Chlorobenzoyl






559




CH


3






CH


3






2-Cyanobenzoyl






560




CH


3






CH


3






3-Cyanobenzoyl






561




CH


3






CH


3






4-Cyanobenzoyl






562




CH


3






CH


3






4-Methoxybenzoyl






563




CH


3






CH


3






2-Pyridylcarbonyl






564




CH


3






CH


3






3-Pyridylcarbonyl






565




CH


3






CH


3






4-Pyridylcarbonyl






566




CH


3






CH


3






2-Pyrimidinylcarbonyl






567




CH


3






CH


3






2-Oxazolylcarbonyl






568




CH


3






CH


3






4-Methylisoxazol-5-yl-carbonyl






569




CH


3






CH


3






Methylsulfonyl






570




CH


3






CH


3






Ethylsulfonyl






571




CH


3






CH


3






n-Propylsulfonyl






572




CH


3






CH


3






i-Propylsulfonyl






573




CH


3






CH


3






n-Butylsulfonyl






574




CH


3






CH


3






t-Butylsulfonyl






575




CH


3






CH


3






n-Pentylsulfonyl






576




CH


3






CH


3






neo-Pentylsulfonyl






577




CH


3






CH


3






n-Hexylsulfonyl






578




CH


3






CH


3






n-Octylsulfonyl






579




CH


3






CH


3






Phenylsulfonyl






580




CH


3






CH


3






2-Chlorophenylsulfonyl






581




CH


3






CH


3






3-Chlorophenylsulfonyl






582




CH


3






CH


3






4-Chlorophenylsulfonyl






583




CH


3






CH


3






2-Cyanophenylsulfonyl






584




CH


3






CH


3






3-Cyanophenylsulfonyl






585




CH


3






CH


3






4-Cyanophenylsulfonyl






586




CH


3






CH


3






2-Pyridylsulfonyl






587




CH


3






CH


3






3-Pyridylsulfonyl






588




CH


3






CH


3






4-Pyridylsulfonyl






589




CH


3






CH


3






2-Pyrimidinylsulfonyl






590




CH


3






CH


3






4-Oxazolylsulfonyl






591




CH


3






CH


3






5-Chlorothiazol-2-yl-sulfonyl






592




CH


3






CH


3






2-t-C


4


H


9


—C


6


H


4


—CH


2








593




CH


3






CH


3






3-t-C


4


H


9


—C


6


H


4


—CH


2








594




CH


3






CH


3






4-t-C


4


H


9


—C


6


H


4


—CH


2








595




CH


3






CH


3






2-(4′-Chlorothiazol-2′-yl-









oxy)eth-1-yl






596




CH


3






CH


3






2-(1′-Methylpyrazol-4′-yl-









oxy)eth-1-yl






597




CH


3






CH


3






4-Br—C


6


H


4








598




CH


3






CH


3






3,5-(CH


3


)


2


—C


6


H


3








599




CH


3






CH


3






4-C


2


H


5


—C


6


H


4








600




CH


3






CH


3






3-Dimethylaminocarbonyl-C


6


H


4








601




CH


3






CH


3






4-Dimethylaminocarbonyl-C


6


H


4








602




CH


3






CH


3






2-Hydroxyprop-1-y1






603




CH


3






CH


3






6-Hydroxy-2-methyl-









pyrimidin-4-ylmethyl






604




CH


3






CH


3






[6-OH,2-CH(CH


3


)


2


-pyrimidin-









4-yl]-CH


2








605




CH


3






CH


3






[6-OH,2-CH(CH


2


)


2


-pyrimidin-









4-yl]-CH


2








606




CH


3






CH


3






5-(2′-Furan)-pent-1-yl






607




CH


3






CH


3






5-(2′-N-Methylpyr-









rol)-pent-1-yl






608




CH


3






CH


3






[2-(4-Cl—C


6


H


4


)-oxazol-4-yl]-









CH


2








609




CH


3






CH


3






3-CF


3


-pyridin-2-yl






610




CH


3






CH


3






5-CF


3


-pyridin-2-yl






611




CH


3






CH


3






6-(2′-Thienyl)hex-1-yl






612




CH


3






t-C


4


H


9






H






613




CH


3






t-C


4


H


9






CH


3








614




CH


3






t-C


4


H


9






C


2


H


5








615




CH


3






t-C


4


H


9






n-C


3


H


7








616




CH


3






t-C


4


H


9






i-C


3


H


7








617




CH


3






t-C


4


H


9






Cyclopropyl






618




CH


3






t-C


4


H


9






n-C


4


H


9








619




CH


3






t-C


4


H


9






t-C


4


H


9








620




CH


3






t-C


4


H


9






n-C


6


H


13








621




CH


3






t-C


4


H


9






(E)-1-Chloropropen-3-yl






622




CH


3






t-C


4


H


9






Propyn-3-yl






623




CH


3






t-C


4


H


9






3-Methylbut-2-en-1-yl






624




CH


3






t-C


4


H


9






2-Naphthyl-CH


2








625




CH


3






t-C


4


H


9






4-Cl—C


6


H


4


—CH


2








626




CH


3






t-C


4


H


9






(E)-4-(4′-Chlorophenyl)but-









2-en-1-yl






627




CH


3






t-C


4


H


9






6-(4′-Chlorophenyl)hex-1-yl






628




CH


3






t-C


4


H


9






3-CF


3


—C


6


H


4








629




CH


3






C


6


H


5






H






630




CH


3






C


6


H


5






CH


3








631




CH


3






C


6


H


5






C


2


H


5









632




CH


3






C


6


H


5






n-C


3


H


7








633




CH


3






C


6


H


5






i-C


3


H


7








634




CH


3






C


6


H


5






Cyclopropyl






635




CH


3






C


6


H


5






n-C


4


H


9








636




CH


3






C


6


H


5






t-C


4


H


9








637




CH


3






C


6


H


5






n-C


6


H


13








638




CH


3






C


6


H


5






4-Cl—C


6


H


4


—CH


2








639




CH


3






C


6


H


5






3-CF


3


—C


6


H


4








640




CH


3






C


6


H


5






6-(4′-Chlorophenyl)hex-1-yl






641




CH


3






C


6


H


5






(E)-4-(4′-Chlorophenyl)but-









2-en-1-yl






642




CH


3






H




H






643




CH


3






H




CH


3








644




CH


3






H




C


2


H


5









645




CH


3






H




n-C


3


H


7








646




CH


3






H




i-C


3


H


7








647




CH


3






OH




H






648




CH


3






OH




CH


3








649




CH


3






OH




C


2


H


5









650




CH


3






OH




n-C


3


H


7








651




CH


3






OH




i-C


3


H


7








652




CH


3






Cl




CH


3








653




CH


3






Cl




C


2


H


5









654




CH


3






Cl




n-C


3


H


7








655




CH


3






Cl




i-C


3


H


7








656




CH


3






OCH


3






H






657




CH


3






OCH


3






CH


3








658




CH


3






OCH


3






C


2


H


5









659




CH


3






OCH


3






n-C


3


H


7








660




CH


3






OCH


3






i-C


3


H


7








661




CH


3






SCH


3






H






662




CH


3






SCH


3






CH


3








663




CH


3






SCH


3






C


2


H


5









664




CH


3






SCH


3






n-C


3


H


7








665




CH


3






SCH


3






i-C


3


H


7








666




CH


3






Cyclopropyl




H






667




CH


3






Cyclopropyl




CH


3








668




CH


3






Cyclopropyl




C


2


H


5









669




CH


3






Cyclopropyl




n-C


3


H


7








670




CH


3






Cyclopropyl




i-C


3


H


7








671




CH


3






2-Pyridyl




H






672




CH


3






2-Pyridyl




CH


3








673




CH


3






2-Pyridyl




C


2


H


5









674




CH


3






2-Pyridyl




n-C


3


H


7








675




CH


3






2-Pyridyl




i-C


3


H


7








676




CH


3






3-Pyridyl




H






677




CH


3






3-Pyridyl




CH


3








678




CH


3






3-Pyridyl




C


2


H


5









679




CH


3






3-Pyridyl




n-C


3


H


7








680




CH


3






3-Pyridyl




i-C


3


H


7








681




CH


3






4-Pyridyl




H






682




CH


3






4-Pyridyl




CH


3








683




CH


3






4-Pyridyl




C


2


H


5









684




CH


3






4-Pyridyl




n-C


3


H


7








685




CH


3






4-Pyridyl




i-C


3


H


7








686




CH


3






2-Pyridimidyl




H






687




CH


3






2-Pyridimidyl




CH


3








688




CH


3






2-Pyridimidyl




C


2


H


5









689




CH


3






2-Pyridimidyl




n-C


3


H


7








690




CH


3






2-Pyridimidyl




i-C


3


H


7








691




CH


3






4-Pyridimidy




H






692




CH


3






4-Pyridimidyl




CH


3








693




CH


3






4-Pyridimidyl




C


2


H


5









694




CH


3






4-Pyridimidyl




n-C


3


H


7








695




CH


3






4-Pyridimidyl




i-C


3


H


7








696




CH


3






5-Pyridimidyl




H






697




CH


3






5-Pyridimidyl




CH


3








698




CH


3






5-Pyridimidyl




C


2


H


5









699




CH


3






5-Pyridimidyl




n-C


3


H


7








700




CH


3






5-Pyridimidyl




i-C


3


H


7








701




CH


3






1,3,5-Triazinyl




H






702




CH


3






1,3,5-Triazinyl




CH


3








703




CH


3






1,3,5-Triazinyl




C


2


H


5









704




CH


3






1,3,5-Triazinyl




n-C


3


H


7








705




CH


3






1,3,5-Triazinyl




i-C


3


H


7








706




CH


3






2-Furyl




H






707




CH


3






2-Furyl




CH


3








708




CH


3






2-Furyl




C


2


H


5









709




CH


3






2-Furyl




n-C


3


H


7








710




CH


3






2-Furyl




i-C


3


H


7








711




CH


3






3-Furyl




H






712




CH


3






3-Furyl




CH


3








713




CH


3






3-Furyl




C


2


H


5









714




CH


3






3-Furyl




n-C


3


H


7








715




CH


3






3-Furyl




i-C


3


H


7








716




CH


3






2-Thienyl




H






717




CH


3






2-Thienyl




CH


3








718




CH


3






2-Thienyl




C


2


H


5









719




CH


3






2-Thienyl




n-C


3


H


7








720




CH


3






2-Thienyl




i-C


3


H


7








721




CH


3






3-Thienyl




H






722




CH


3






3-Thienyl




CH


3








723




CH


3






3-Thienyl




C


2


H


5









724




CH


3






3-Thienyl




n-C


3


H


7








725




CH


3






3-Thienyl




i-C


3


H


7








726




CH


3






2-Oxazolyl




H






727




CH


3






2-Oxazolyl




CH


3








728




CH


3






2-Oxazolyl




C


2


H


5









729




CH


3






2-Oxazolyl




n-C


3


H


7








730




CH


3






2-Oxazolyl




i-C


3


H


7








731




CH


3






4-Oxazolyl




H






732




CH


3






4-Oxazolyl




CH


3








733




CH


3






4-Oxazolyl




C


2


H


5









734




CH


3






4-Oxazolyl




n-C


3


H


7








735




CH


3






4-Oxazolyl




i-C


3


H


7








736




CH


3






2-Thiazolyl




H






737




CH


3






2-Thiazolyl




CH


3








738




CH


3






2-Thiazolyl




C


2


H


5









739




CH


3






2-Thiazolyl




n-C


3


H


7








740




CH


3






2-Thiazolyl




i-C


3


H


7








741




CH


3






4-Thiazolyl




H






742




CH


3






4-Thiazolyl




CH


3








743




CH


3






4-Thiazolyl




C


2


H


5









744




CH


3






4-Thiazolyl




n-C


3


H


7








745




CH


3






4-Thiazolyl




i-C


3


H


7








746




CH


3






3-Isoxazolyl




H






747




CH


3






3-Isoxazolyl




CH


3








748




CH


3






3-Isoxazolyl




C


2


H


5









749




CH


3






3-Isoxazolyl




n-C


3


H


7








750




CH


3






3-Isoxazolyl




i-C


3


H


7








751




CH


3






5-Isoxazolyl




H






752




CH


3






5-Isoxazolyl




CH


3








753




CH


3






5-Isoxazolyl




C


2


H


5









754




CH


3






5-Isoxazolyl




n-C


3


H


7








755




CH


3






5-Isoxazolyl




i-C


3


H


7








756




CH


3






2-Imidazolyl




H






757




CH


3






2-Imidazolyl




CH


3








758




CH


3






2-Imidazolyl




C


2


H


5









759




CH


3






2-Imidazolyl




n-C


3


H


7








760




CH


3






2-Imidazolyl




i-C


3


H


7








761




CH


3






3-Pyrazolyl




H






762




CH


3






3-Pyrazolyl




CH


3








763




CH


3






3-Pyrazolyl




C


2


H


5









764




CH


3






3-Pyrazolyl




n-C


3


H


7








765




CH


3






3-Pyrazolyl




i-C


3


H


7








766




CH


3






4-Pyrazolyl




H






767




CH


3






4-Pyrazolyl




CH


3








768




CH


3






4-Pyrazolyl




C


2


H


5









769




CH


3






4-Pyrazolyl




n-C


3


H


7








770




CH


3






4-Pyrazolyl




i-C


3


H


7








771




OCH


3






H




H






772




OCH


3






H




CH


3








773




OCH


3






H




C


2


H


5









774




OCH


3






H




n-C


3


H


7








775




OCH


3






H




i-C


3


H


7








776




OCH


3






OH




H






777




OCH


3






OH




CH


3








776




OCH


3






OH




C


2


H


5









779




OCH


3






OH




n-C


3


H


7








780




OCH


3






OH




i-C


3


H


7








781




OCH


3






Cl




n-C


4


H


9








782




OCH


3






Cl




CH


3








783




OCH


3






Cl




C


2


H


5









784




OCH


3






Cl




n-C


3


H


7








785




OCH


3






Cl




i-C


3


H


7








786




OCH


3






OCH


3






H






787




OCH


3






OCH


3






CH


3








788




OCH


3






OCH


3






C


2


H


5









789




OCH


3






OCH


3






n-C


3


H


7








790




OCH


3






OCH


3






i-C


3


H


7








791




OCH


3






SCH


3






H






792




OCH


3






SCH


3






CH


3








793




OCH


3






SCH


3






C


2


H


5









794




OCH


3






SCH


3






n-C


3


H


7








795




OCH


3






SCH


3






i-C


3


H


7








796




OCH


3






CH


3






H






797




OCH


3






CH


3






CH


3








798




OCH


3






CH


3






C


2


H


5









799




OCH


3






CH


3






n-C


3


H


7








800




OCH


3






CH


3






i-C


3


H


7








801




OCH


3






Cyclopropyl




H






802




OCH


3






Cyclopropyl




CH


3








803




OCH


3






Cyclopropyl




C


2


H


5









804




OCH


3






Cyclopropyl




n-C


3


H


7








805




OCH


3






Cyclopropyl




i-C


3


H


7








806




OCH


3






2-Pyridyl




H






807




OCH


3






2-Pyridyl




CH


3








808




OCH


3






2-Pyridyl




C


2


H


5









809




OCH


3






2-Pyridyl




n-C


3


H


7








810




OCH


3






2-Pyridyl




i-C


3


H


7








811




OCH


3






3-Pyridyl




H






812




OCH


3






3-Pyridyl




CH


3








813




OCH


3






3-Pyridyl




C


2


H


5









814




OCH


3






3-Pyridyl




n-C


3


H


7








815




OCH


3






3-Pyridyl




i-C


3


H


7








816




OCH


3






4-Pyridyl




H






817




OCH


3






4-Pyridyl




CH


3








818




OCH


3






4-Pyridyl




C


2


H


5









819




OCH


3






4-Pyridyl




n-C


3


H


7








820




OCH


3






4-Pyrimidyl




i-C


3


H


7








821




OCH


3






2-Pyrimidyl




H






822




OCH


3






2-Pyrimidyl




CH


3








823




OCH


3






2-Pyrimidyl




C


2


H


5









824




OCH


3






2-Pyrimidyl




n-C


3


H


7








825




OCH


3






2-Pyrimidyl




i-C


3


H


7








826




OCH


3






4-Pyrimidyl




H






827




OCH


3






4-Pyrimidyl




CH


3








828




OCH


3






4-Pyrimidyl




C


2


H


5









829




OCH


3






4-Pyrimidyl




n-C


3


H


7








830




OCH


3






4-Pyrimidyl




i-C


3


H


7








831




OCH


3






5-Pyrimidyl




H






832




OCH


3






5-Pyrimidyl




CH


3








833




OCH


3






5-Pyrimidyl




C


2


H


5









834




OCH


3






5-Pyrimidyl




n-C


3


H


7








835




OCH


3






5-Pyrimidyl




i-C


3


H


7








836




OCH


3






1,3,5-Triazinyl




H






837




OCH


3






1,3,5-Triazinyl




CH


3








838




OCH


3






1,3,5-Triazinyl




C


2


H


5









839




OCH


3






1,3,5-Triazinyl




n-C


3


H


7








840




OCH


3






1,3,5-Triazinyl




i-C


3


H


7








841




OCH


3






2-Furyl




H






842




OCH


3






2-Furyl




CH


3








843




OCH


3






2-Furyl




C


2


H


5









844




OCH


3






2-Furyl




n-C


3


H


7








845




OCH


3






2-Furyl




i-C


3


H


7








846




OCH


3






3-Furyl




H






847




OCH


3






3-Furyl




CH


3








848




OCH


3






3-Furyl




C


2


H


5









849




OCH


3






3-Furyl




n-C


3


H


7








850




OCH


3






3-Furyl




i-C


3


H


7








851




OCH


3






2-Thienyl




H






852




OCH


3






2-Thienyl




CH


3








853




OCH


3






2-Thienyl




C


2


H


5









854




OCH


3






2-Thienyl




n-C


3


H


7








855




OCH


3






2-Thienyl




i-C


3


H


7








856




OCH


3






3-Thienyl




H






857




OCH


3






3-Thienyl




CH


3








858




OCH


3






3-Thienyl




C


2


H


5









859




OCH


3






3-Thienyl




n-C


3


H


7








860




OCH


3






3-Thienyl




i-C


3


H


7








861




OCH


3






2-Oxazolyl




H






862




OCH


3






2-Oxazolyl




CH


3








863




OCH


3






2-Oxazolyl




C


2


H


5









864




OCH


3






2-Oxazolyl




n-C


3


H


7








865




OCH


3






2-Oxazolyl




i-C


3


H


7








866




OCH


3






4-Oxazolyl




H






867




OCH


3






4-Oxazolyl




CH


3








868




OCH


3






4-Oxazolyl




C


2


H


5









869




OCH


3






4-Oxazolyl




n-C


3


H


7








870




OCH


3






4-Oxazolyl




i-C


3


H


7








871




OCH


3






2-Thiazolyl




H






872




OCH


3






2-Thiazolyl




CH


3








873




OCH


3






2-Thiazolyl




C


2


H


5









874




OCH


3






2-Thiazolyl




n-C


3


H


7








875




OCH


3






2-Thiazolyl




i-C


3


H


7








876




OCH


3






4-Thiazolyl




H






877




OCH


3






4-Thiazolyl




CH


3








878




OCH


3






4-Thiazolyl




C


2


H


5









879




OCH


3






4-Thiazolyl




n-C


3


H


7








880




OCH


3






A-Thiazolyl




i-C


3


H


7








881




OCH


3






3-Isoxazolyl




H






882




OCH


3






3-Isoxazolyl




CH


3








883




OCH


3






3-Isoxazolyl




C


2


H


5









884




OCH


3






3-Isoxazolyl




n-C


3


H


7








885




OCH


3






3-Isoxazolyl




i-C


3


H


7








886




OCH


3






5-Isoxazolyl




H






887




OCH


3






5-Isoxazolyl




CH


3








888




OCH


3






5-Isoxazolyl




C


2


H


5









889




OCH


3






5-Isoxazolyl




n-C


3


H


7








890




OCH


3






5-Isoxazolyl




i-C


3


H


7








891




OCH


3






2-Imidazolyl




H






892




OCH


3






2-Imidazolyl




CH


3








893




OCH


3






2-Imidazolyl




C


2


H


5









894




OCH


3






2-Imidazolyl




n-C


3


H


7








895




OCH


3






2-Imidazolyl




i-C


3


H


7








896




OCH


3






3-Pyrazolyl




H






897




OCH


3






3-Pyrazolyl




CH


3








898




OCH


3






3-Pyrazolyl




C


2


H


5









899




OCH


3






3-Pyrazolyl




n-C


3


H


7








900




OCH


3






3-Pyrazolyl




i-C


3


H


7








901




OCH


3






4-Pyrazolyl




H






902




OCH


3






4-Pyrazolyl




CH


3








903




OCH


3






4-Pyrazolyl




C


2


H


5









904




OCH


3






4-Pyrazolyl




n-C


3


H


7








905




OCH


3






4-Pyrazolyl




i-C


3


H


7








906




OH




H




H






907




OH




H




CH


3








908




OH




H




C


2


H


5









909




OH




H




n-C


3


H


7








910




OH




H




i-C


3


H


7








911




OH




OH




H






912




OH




OH




CH


3








913




OH




OH




C


2


H


5









914




OH




OH




n-C


3


H


7








915




OH




OH




i-C


3


H


7








916




OH




Cl




n-C


4


H


9








917




OH




Cl




CH


3








918




OH




Cl




C


2


H


5









919




OH




Cl




n-C


3


H


7








920




OH




Cl




i-C


3


H


7








921




OH




OCH


3






H






922




OH




OCH


3






CH


3








923




OH




OCH


3






C


2


H


5









924




OH




OCH


3






n-C


3


H


7








925




OH




OCH


3






i-C


3


H


7








926




OH




SCH


3






H






927




OH




SCH


3






CH


3








928




OH




SCH


3






C


2


H


5









929




OH




SCH


3






n-C


3


H


7








930




OH




SCH


3






i-C


3


H


7








931




OH




CH


3






H






932




OH




CH


3






CH


3








933




OH




CH


3






C


2


H


5









934




OH




CH


3






n-C


3


H


7








935




OH




CH


3






i-C


3


H


7








936




OH




Cyclopropyl




H






937




OH




Cyclopropyl




CH


3








938




OH




Cyclopropyl




C


2


H


5









939




OH




Cyclopropyl




n-C


3


H


7








940




OH




Cyclopropyl




i-C


3


H


7








941




OH




2-Pyridyl




H






942




OH




2-Pyridyl




CH


3








943




OH




2-Pyridyl




C


2


H


5









944




OH




2-Pyridyl




n-C


3


H


7








945




OH




2-Pyridyl




i-C


3


H


7








946




OH




3-Pyridyl




H






947




OH




3-Pyridyl




CH


3








948




OH




3-Pyridyl




C


2


H


5









949




OH




3-Pyridyl




n-C


3


H


7








950




OH




3-Pyridyl




i-C


3


H


7








951




OH




4-Pyridyl




H






952




OH




4-Pyridyl




CH


3








953




OH




4-Pyridyl




C


2


H


5









954




OH




4-Pyridyl




n-C


3


H


7








955




OH




4-Pyridyl




i-C


3


H


7








956




OH




2-Pyrimidyl




H






957




OH




2-Pyrimidyl




CH


3








958




OH




2-Pyrimidyl




C


2


H


5









959




OH




2-Pyrimidyl




n-C


3


H


7








960




OH




2-Pyrimidyl




i-C


3


H


7








961




OH




4-Pyrimidyl




H






962




OH




4-Pyrimidyl




CH


3








963




OH




4-Pyrimidyl




C


2


H


5









964




OH




4-Pyrimidyl




n-C


3


H


7








965




OH




4-Pyrimidyl




i-C


3


H


7








966




OH




5-Pyrimidyl




H






967




OH




5-Pyrimidyl




CH


3








968




OH




5-Pyrimidyl




C


2


H


5









969




OH




5-Pyrimidyl




n-C


3


H


7








970




OH




5-Pyrimidyl




i-C


3


H


7








971




OH




1,3,5-Triazinyl




H






972




OH




1,3,5-Triazinyl




CH


3








973




OH




1,3,5-Triazinyl




C


2


H


5









974




OH




1,3,5-Triazinyl




n-C


3


H


7








975




OH




1,3,5-Triazinyl




i-C


3


H


7








976




OH




2-Furyl




H






977




OH




2-Furyl




CH


3








978




OH




2-Furyl




C


2


H


5









979




OH




2-Furyl




n-C


3


H


7








980




OH




2-Furyl




i-C


3


H


7








981




OH




3-Furyl




H






982




OH




3-Furyl




CH


3








983




OH




3-Furyl




C


2


H


5









984




OH




3-Furyl




n-C


3


H


7








985




OH




3-Furyl




i-C


3


H


7








986




OH




2-Thienyl




H






987




OH




2-Thienyl




CH


3








988




OH




2-Thienyl




C


2


H


5









989




OH




2-Thienyl




n-C


3


H


7








990




OH




2-Thienyl




i-C


3


H


7








991




OH




3-Thienyl




H






992




OH




3-Thienyl




CH


3








993




OH




3-Thienyl




C


2


H


5









994




OH




3-Thienyl




n-C


3


H


7








995




OH




3-Thienyl




i-C


3


H


7








996




OH




2-Oxazolyl




H






997




OH




2-Oxazolyl




CH


3








998




OH




2-Oxazolyl




C


2


H


5









999




OH




2-Oxazolyl




n-C


3


H


7








1000




OH




2-Oxazolyl




i-C


3


H


7








1001




OH




4-Oxazolyl




H






1002




OH




4-Oxazolyl




CH


3








1003




OH




4-Oxazolyl




C


2


H


5









1004




QH




4-Oxazolyl




n-C


3


H


7








1005




OH




2-Thiazolyl




i-C


3


H


7








1006




OH




2-Thiazolyl




H






1007




OH




2-Thiazolyl




CH


3








1008




OH




2-Thiazolyl




C


2


H


5









1009




OH




2-Thiazolyl




n-C


3


H


7








1010




OH




2-Thiazolyl




i-C


3


H


7








1011




OH




4-Thiazolyl




H






1012




OH




4-Thiazolyl




CH


3








1013




OH




4-Thiazolyl




C


2


H


5









1014




OH




4-Isoxazolyl




n-C


3


H


7








1015




OH




4-Isoxazolyl




i-C


3


H


7








1016




OH




3-Isoxazolyl




H






1017




OH




3-Isoxazolyl




CH


3








1018




OH




3-Isoxazolyl




C


2


H


5









1019




OH




3-Isoxazolyl




n-C


3


H


7








1020




OH




3-Isoxazolyl




i-C


3


H


7








1021




OH




5-Isoxazolyl




H






1022




OH




5-Isoxazolyl




CH


3








1023




OH




5-Isoxazolyl




C


2


H


5









1024




OH




5-Isoxazolyl




n-C


3


H


7








1025




OH




5-Isoxazolyl




i-C


3


H


7








1026




OH




2-Imidazolyl




H






1027




OH




2-Imidazolyl




CH


3








1028




OH




2-Imidazolyl




C


2


H


5









1029




OH




2-Imidazolyl




n-C


3


H


7








1030




OH




2-Imidazolyl




i-C


3


H


7








1031




OH




3-Pyrazolyl




H






1032




OH




3-Pyrazolyl




CH


3








1033




OH




3-Pyrazolyl




C


2


H


5









1034




OH




3-Pyrazolyl




n-C


3


H


7








1035




OH




3-Pyrazolyl




i-C


3


H


7








1036




OH




4-Pyrazolyl




H






1037




OH




4-Pyrazolyl




CH


3








1038




OH




4-Pyrazolyl




C


2


H


5









1039




OH




4-Pyrazolyl




n-C


3


H


7








1040




OH




4-Pyrazolyl




i-C


3


H


7








1041




H




H




H






1042




H




H




CH


3








1043




H




H




C


2


H


5









1044




H




H




n-C


3


H


7








1045




H




H




i-C


3


H


7








1046




H




OH




H






1047




H




OH




CH


3








1048




H




OH




C


2


H


5









1049




H




OH




n-C


3


H


7








1050




H




OH




i-C


3


H


7








1051




H




Cl




n-C


4


H


9








1052




H




Cl




CH


3








1053




H




Cl




C


2


H


5









1054




H




Cl




n-C


3


H


7








1055




H




Cl




i-C


3


H


7








1056




H




OCH


3






H






1057




H




OCH


3






CH


3








1058




H




OCH


3






C


2


H


5









1059




H




OCH


3






n-C


3


H


7








1060




H




OCH


3






i-C


3


H


7








1061




H




CH


3






H






1062




H




CH


3






CH


3








1063




H




CH


3






C


2


H


5









1064




H




CH


3






n-C


3


H


7








1065




H




CH


3






i-C


3


H


7








1066




H




Cyclopropyl




H






1067




H




Cyclopropyl




CH


3








1068




H




Cyclopropyl




C


2


H


5









1069




H




Cyclopropyl




n-C


3


H


7








1070




H




Cyclopropyl




i-C


3


H


7








1071




Cl




H




H






1072




Cl




H




CH


3








1073




Cl




H




C


2


H


5









1074




Cl




H




n-C


3


H


7








1075




Cl




H




i-C


3


H


7








1076




Cl




OH




H






1077




Cl




OH




CH


3








1078




Cl




OH




C


2


H


5









1079




Cl




OH




n-C


3


H


7








1080




Cl




OH




i-C


3


H


7








1081




Cl




Cl




n-C


4


H


9








1082




Cl




Cl




CH


3








1083




Cl




Cl




C


2


H


5









1084




Cl




Cl




n-C


3


H


7








1085




Cl




Cl




i-C


3


H


7








1086




Cl




OCH


3






H






1087




Cl




OCH


3






CH


3








1088




Cl




OCH


3






C


2


H


5









1089




Cl




OCH


3






n-C


3


H


7








1090




Cl




OCH


3






i-C


3


H


7








1091




Cl




CH


3






H






1092




Cl




CH


3






CH


3








1093




Cl




CH


3






C


2


H


5









1094




Cl




CH


3






n-C


3


H


7








1095




Cl




CH


3






i-C


3


H


7








1096




Cl




Cyclopropyl




H






1097




Cl




Cyclopropyl




CH


3








1098




Cl




Cyclopropyl




C


2


H


5









1099




Cl




Cyclopropyl




n-C


3


H


7








1100




Cl




Cyclopropyl




i-C


3


H


7








1101




SCH


3






H




H






1102




SCH


3






H




CH


3








1103




SCH


3






H




C


2


H


5









1104




SCH


3






H




n-C


3


H


7








1105




SCH


3






H




i-C


3


H


7








1106




SCH


3






OH




H






1107




SCH


3






OH




CH


3








1108




SCH


3






OH




C


2


H


5









1109




SCH


3






OH




n-C


3


H


7








1110




SCH


3






OH




i-C


3


H


7








1111




SCH


3






CH


3






H






1112




SCH


3






CH


3






CH


3








1113




SCH


3






CH


3






C


2


H


5









1114




SCH


3






CH


3






n-C


3


H


7








1115




SCH


3






CH


3






i-C


3


H


7








1116




SCH


3






SCH


3






H






1117




SCH


3






SCH


3






CH


3








1118




SCH


3






SCH


3






C


2


H


5









1119




SCH


3






SCH


3






n-C


3


H


7








1120




SCH


3






SCH


3






i-C


3


H


7








1121




SCH


3






Cyclopropyl




H






1122




SCH


3






Cyclopropyl




CH


3








1123




SCH


3






Cyclopropyl




C


2


H


5









1124




SCH


3






Cyclopropyl




n-C


3


H


7








1125




SCH


3






Cyclopropyl




i-C


3


H


7








1126




Cyclo-




H




H







propyl






1127




Cyclo-




H




CH


3









propyl






1128




Cyclo-




H




C


2


H


5










propyl






1129




Cyclo-




H




n-C


3


H


7









propyl






1130




Cyclo-




H




i-C


3


H


7









propyl






1131




Cyclo-




OH




H







propyl






1132




Cyclo-




OH




CH


3









propyl






1133




Cyclo-




OH




C


2


H


5










propyl






1134




Cyclo-




OH




n-C


3


H


7









propyl






1135




Cyclo-




OH




i-C


3


H


7









propyl






1136




Cyclo-




Cl




n-C


4


H


9









propyl






1137




Cyclo-




Cl




CH


3









propyl






1138




Cyclo-




Cl




C


2


H


5










propyl






1139




Cyclo-




Cl




n-C


3


H


7









propyl






1140




Cyclo-




Cl




i-C


3


H


7









propyl






1141




Cyclo-




OCH


3






H







propyl






1142




Cyclo-




OCH


3






CH


3









propyl






1143




Cyclo-




OCH


3






C


2


H


5










propyl






1144




Cyclo-




OCH


3






n-C


3


H


7









propyl






1145




Cyclo-




OCH


3






i-C


3


H


7









propyl






1146




Cyclo-




SCH


3






H







propyl






1147




Cyclo-




SCH


3






CH


3









propyl






1148




Cyclo-




SCH


3






C


2


H


5










propyl






1149




Cyclo-




SCH


3






n-C


3


H


7









propyl






1150




Cyclo-




SCH


3






i-C


3


H


7









propyl






1151




Cyclo-




CH


3






H







propyl






1152




Cyclo-




CH


3






CH


3









propyl






1153




Cyclo-




CH


3






C


2


H


5










propyl






1154




Cyclo-




CH


3






n-C


3


H


7









propyl






1155




Cyclo-




CH


3






i-C


3


H


7









propyl






1156




CH


3






2-F—C


6


H


4






CH


3








1157




CH


3






2-F—C


6


H


4






C


2


H


5









1158




CH


3






2-F—C


6


H


4






n-C


3


H


7








1159




CH


3






2-F—C


6


H


4






i-C


3


H


7








1160




CH


3






2-F—C


6


H


4






n-C


4


H


9








1161




CH


3






2-F—C


6


H


4






t-C


4


H


9








1162




CH


3






2-F—C


6


H


4






n-C


6


H


13








1163




CH


3






2-F—C


6


H


4






Prop-1-en-3-yl






1164




CH


3






2-F—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1165




CH


3






2-F—C


6


H


4






Propyn-3-yl






1166




CH


3






2-F—C


6


H


4






3-Methyl-but-2-en-1-yl






1167




CH


3






3-F—C


6


H


4






H






1168




CH


3






3-F—C


6


H


4






CH


3








1169




CH


3






3-F—C


6


H


4






C


2


H


5









1170




CH


3






3-F—C


6


H


4






n-C


3


H


7








1171




CH


3






3-F—C


6


H


4






i-C


3


H


7








1172




CH


3






3-F—C


6


H


4






n-C


4


H


9








1173




CH


3






3-F—C


6


H


4






t-C


4


H


9








1174




CH


3






3-F—C


6


H


4






n-C


6


H


13








1175




CH


3






3-F—C


6


H


4






Prop-1-en-3-yl






1176




CH


3






3-F—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1177




CH


3






3-F—C


6


H


4






Propyn-3-yl






1178




CH


3






3-F—C


6


H


4






3-Methyl-but-2-en-1-yl






1179




CH


3






4-F—C


6


H


4






H






1180




CH


3






4-F—C


6


H


4






CH


3








1181




CH


3






4-F—C


6


H


4






C


2


H


5









1182




CH


3






4-F—C


6


H


4






n-C


3


H


7








1183




CH


3






4-F—C


6


H


4






i-C


3


H


7








1184




CH


3






4-F—C


6


H


4






n-C


4


H


9








1185




CH


3






4-F—C


6


H


4






t-C


4


H


9








1186




CH


3






4-F—C


6


H


4






n-C


6


H


13








1187




CH


3






4-F—C


6


H


4






Prop-1-en-3-yl






1188




CH


3






4-F—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1189




CH


3






4-F—C


6


H


4






Propyn-3-yl






1190




CH


3






4-F—C


6


H


4






3-Methyl-but-2-en-1-yl






1191




CH


3






2-Cl—C


6


H


4






H






1192




CH


3






2-Cl—C


6


H


4






CH


3








1193




CH


3






2-Cl—C


6


H


4






C


2


H


5









1194




CH


3






2-Cl—C


6


H


4






n-C


3


H


7








1195




CH


3






2-Cl—C


6


H


4






i-C


3


H


7








1196




CH


3






2-Cl—C


6


H


4






n-C


4


H


9








1197




CH


3






2-Cl—C


6


H


4






t-C


4


H


9








1198




CH


3






2-Cl—C


6


H


4






n-C


6


H


13








1199




CH


3






2-Cl—C


6


H


4






Prop-1-en-3-yl






1200




CH


3






2-Cl—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1201




CH


3






2-Cl—C


6


H


4






Propyn-3-yl






1202




CH


3






2-Cl—C


6


H


4






3-Methyl-but-2-en-1-yl






1203




CH


3






3-Cl—C


6


H


4






H






1204




CH


3






3-Cl—C


6


H


4






CH


3








1205




CH


3






3-Cl—C


6


H


4






C


2


H


5









1206




CH


3






3-Cl—C


6


H


4






n-C


3


H


7








1207




CH


3






3-Cl—C


6


H


4






i-C


3


H


7








1208




CH


3






3-Cl—C


6


H


4






n-C


4


H


9








1209




CH


3






3-Cl—C


6


H


4






t-C


4


H


9








1210




CH


3






3-Cl—C


6


H


4






n-C


6


H


13








1211




CH


3






3-Cl—C


6


H


4






Prop-1-en-3-yl






1212




CH


3






3-Cl—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1213




CH


3






3-Cl—C


6


H


4






Propyn-3-yl






1214




CH


3






3-Cl—C


6


H


4






3-Methyl-but-2-en-1-yl






1215




CH


3






4-Cl—C


6


H


4






H






1216




CH


3






4-Cl—C


6


H


4






CH


3








1217




CH


3






4-Cl—C


6


H


4






C


2


H


5









1218




CH


3






4-Cl—C


6


H


4






n-C


3


H


7








1219




CH


3






4-Cl—C


6


H


4






i-C


3


H


7








1220




CH


3






4-Cl—C


6


H


4






n-C


4


H


9








1221




CH


3






4-Cl—C


6


H


4






t-C


4


H


9








1222




CH


3






4-Cl—C


6


H


4






n-C


6


H


13








1223




CH


3






4-Cl—C


6


H


4






Prop-1-en-3-yl






1224




CH


3






4-Cl—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1225




CH


3






4-Cl—C


6


H


4






Propyn-3-yl






1226




CH


3






4-Cl—C


6


H


4






3-Methyl-but-2-en-1-yl






1227




CH


3






2,3-Cl


2


—C


6


H


3






H






1228




CH


3






2,3-Cl


2


—C


6


H


3






CH


3








1229




CH


3






2,3-Cl


2


—C


6


H


3






C


2


H


5









1230




CH


3






2,3-Cl


2


—C


6


H


3






n-C


3


H


7








1231




CH


3






2,3-Cl


2


—C


6


H


3






i-C


3


H


7








1232




CH


3






2,3-Cl


2


—C


6


H


3






n-C


4


H


9








1233




CH


3






2,3-Cl


2


—C


6


H


3






t-C


4


H


9








1234




CH


3






2,3-Cl


2


—C


6


H


3






n-C


6


H


13








1235




CH


3






2,3-Cl


2


—C


6


H


3






Prop-1-en-3-yl






1236




CH


3






2,3-Cl


2


—C


6


H


3






(E)-1-Chloroprop-1-en-3-yl






1237




CH


3






2,3-Cl


2


—C


6


H


3






Propyn-3-yl






1238




CH


3






2,3-Cl


2


—C


6


H


3






3-Methyl-but-2-en-1-yl






1239




CH


3






2,4-Cl


2


—C


6


H


3






H






1240




CH


3






2,4-Cl


2


—C


6


H


3






CH


3








1241




CH


3






2,4-Cl


2


—C


6


H


3






C


2


H


5









1242




CH


3






2,4-Cl


2


—C


6


H


3






n-C


3


H


7








1243




CH


3






2,4-Cl


2


—C


6


H


3






i-C


3


H


7








1244




CH


3






2,4-Cl


2


—C


6


H


3






n-C


4


H


9








1245




CH


3






2,4-Cl


2


—C


6


H


3






t-C


4


H


9








1246




CH


3






2,4-Cl


2


—C


6


H


3






n-C


6


H


13








1247




CH


3






2,4-Cl


2


—C


6


H


3






Prop-1-en-3-yl






1248




CH


3






2,4-Cl


2


—C


6


H


3






(E)-1-Chloroprop-1-en-3-yl






1249




CH


3






2,4-Cl


2


—C


6


H


3






Propyn-3-yl






1250




CH


3






2,4-Cl


2


—C


6


H


3






3-Methyl-but-2-en-1-yl






1251




CH


3






2,5-Cl


2


—C


6


H


3






H






1252




CH


3






2,5-Cl


2


—C


6


H


3






CH


3








1253




CH


3






2,5-Cl


2


—C


6


H


3






C


2


H


5









1254




CH


3






2,5-Cl


2


—C


6


H


3






n-C


3


H


7








1255




CH


3






2,5-Cl


2


—C


6


H


3






i-C


3


H


7








1256




CH


3






2,5-Cl


2


—C


6


H


3






n-C


4


H


9








1257




CH


3






2,5-Cl


2


—C


6


H


3






t-C


4


H


9








1258




CH


3






2,5-Cl


2


—C


6


H


3






n-C


6


H


13








1259




CH


3






2,5-Cl


2


—C


6


H


3






Prop-1-en-3-yl






1260




CH


3






2,5-Cl


2


—C


6


H


3






(E)-1-Chloroprop-1-en-3-yl






1261




CH


3






2,5-Cl


2


—C


6


H


3






Propyn-3-yl






1262




CH


3






2,5-Cl


2


—C


6


H


3






3-Methyl-but-2-en-1-yl






1263




CH


3






2,6-Cl


2


—C


6


H


3






H






1264




CH


3






2,6-Cl


2


—C


6


H


3






CH


3








1265




CH


3






2,6-Cl


2


—C


6


H


3






C


2


H


5









1266




CH


3






2,6-Cl


2


—C


6


H


3






n-C


3


H


7








1267




CH


3






2,6-Cl


2


—C


6


H


3






i-C


3


H


7








1268




CH


3






2,6-Cl


2


—C


6


H


3






n-C


4


H


9








1269




CH


3






2,6-Cl


2


—C


6


H


3






t-C


4


H


9








1270




CH


3






2,6-Cl


2


—C


6


H


3






n-C


6


H


13








1271




CH


3






2,6-Cl


2


—C


6


H


3






Prop-1-en-3-yl






1272




CH


3






2,6-Cl


2


—C


6


H


3






(E)-1-Chloroprop-1-en-3-yl






1273




CH


3






2,6-Cl


2


—C


6


H


3






Propyn-3-yl






1274




CH


3






2,6-Cl


2


—C


6


H


3






3-Methyl-but-2-en-1-yl






1275




CH


3






3,4-Cl


2


—C


6


H


3






H






1276




CH


3






3,4-Cl


2


—C


6


H


3






CH


3








1277




CH


3






3,4-Cl


2


—C


6


H


3






C


2


H


5









1278




CH


3






3,4-Cl


2


—C


6


H


3






n-C


3


H


7








1279




CH


3






3,4-Cl


2


—C


6


H


3






i-C


3


H


7








1280




CH


3






3,4-Cl


2


—C


6


H


3






n-C


4


H


9








1281




CH


3






3,4-Cl


2


—C


6


H


3






t-C


4


H


9








1282




CH


3






3,4-Cl


2


—C


6


H


3






n-C


6


H


13








1283




CH


3






3,4-Cl


2


—C


6


H


3






Prop-1-en-3-yl






1284




CH


3






3,4-Cl


2


—C


6


H


3






(E)-1-Chloroprop-1-en-3-yl






1285




CH


3






3,4-Cl


2


—C


6


H


3






Propyn-3-yl






1286




CH


3






3,4-Cl


2


—C


6


H


3






3-Methyl-but-2-en-1-yl






1287




CH


3






3,5-Cl


2


—C


6


H


3






H






1288




CH


3






3,5-Cl


2


—C


6


H


3






CH


3








1289




CH


3






3,5-Cl


2


—C


6


H


3






C


2


H


5









1290




CH


3






3,5-Cl


2


—C


6


H


3






n-C


3


H


7








1291




CH


3






3,5-Cl


2


—C


6


H


3






i-C


3


H


7








1292




CH


3






3,5-Cl


2


—C


6


H


3






n-C


4


H


9








1293




CH


3






3,5-Cl


2


—C


6


H


3






t-C


4


H


9








1294




CH


3






3,5-Cl


2


—C


6


H


3






n-C


6


H


13








1295




CH


3






3,5-Cl


2


—C


6


H


3






Prop-1-en-3-yl






1296




CH


3






3,5-Cl


2


—C


6


H


3






(E)-1-Chloroprop-1-en-3-yl






1297




CH


3






3,5-Cl


2


—C


6


H


3






Propyn-3-yl






1298




CH


3






3,5-Cl


2


—C


6


H


3






3-Methyl-but-2-en-1-yl






1299




CH


3






2-Br—C


6


H


4






H






1300




CH


3






2-Br—C


6


H


4






CH


3








1301




CH


3






2-Br—C


6


H


4






C


2


H


5









1302




CH


3






2-Br—C


6


H


4






n-C


3


H


7








1303




CH


3






2-Br—C


6


H


4






i-C


3


H


7








1304




CH


3






2-Br—C


6


H


4






n-C


4


H


9








1305




CH


3






2-Br—C


6


H


4






t-C


4


H


9








1306




CH


3






2-Br—C


6


H


4






n-C


6


H


13








1307




CH


3






2-Br—C


6


H


4






Prop-1-en-3-yl






1308




CH


3






2-Br—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1309




CH


3






2-Br—C


6


H


4






Propyn-3-yl






1310




CH


3






2-Br—C


6


H


4






3-Methyl-but-2-en-1-yl






1311




CH


3






3-Br—C


6


H


4






H






1312




CH


3






3-Br—C


6


H


4






CH


3








1313




CH


3






3-Br—C


6


H


4






C


2


H


5









1314




CH


3






3-Br—C


6


H


4






n-C


3


H


7








1315




CH


3






3-Br—C


6


H


4






i-C


3


H


7








1316




CH


3






3-Br—C


6


H


4






n-C


4


H


9








1317




CH


3






3-Br—C


6


H


4






t-C


4


H


9








1318




CH


3






3-Br—C


6


H


4






n-C


6


H


13








1319




CH


3






3-Br—C


6


H


4






Prop-1-en-3-yl






1320




CH


3






3-Br—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1321




CH


3






3-Br—C


6


H


4






Propyn-3-yl






1322




CH


3






3-Br—C


6


H


4






3-Methyl-but-2-en-1-yl






1323




CH


3






4-Br—C


6


H


4






H






1324




CH


3






4-Br—C


6


H


4






CH


3








1325




CH


3






4-Br—C


6


H


4






C


2


H


5









1326




CH


3






4-Br—C


6


H


4






n-C


3


H


7








1327




CH


3






4-Br—C


6


H


4






i-C


3


H


7








1326




CH


3






4-Br—C


6


H


4






n-C


4


H


9








1329




CH


3






4-Br—C


6


H


4






t-C


4


H


9








1330




CH


3






4-Br—C


6


H


4






n-C


6


H


13








1331




CH


3






4-Br—C


6


H


4






Prop-1-en-3-yl






1332




CH


3






4-Br—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1333




CH


3






4-Br—C


6


H


4






Propyn-3-yl






1334




CH


3






4-Br—C


6


H


4






3-Methyl-but-2-en-1-yl






1335




CH


3






2-I—C


4


H


4






H






1336




CH


3






2-I—C


4


H


4






CH


3








1337




CH


3






2-I—C


4


H


4






C


2


H


5









1338




CH


3






2-I—C


4


H


4






n-C


3


H


7








1339




CH


3






2-I—C


4


H


4






i-C


3


H


7








1340




CH


3






2-I—C


4


H


4






n-C


4


H


9








1341




CH


3






2-I—C


4


H


4






t-C


4


H


9








1342




CH


3






2-I—C


4


H


4






n-C


6


H


13








1343




CH


3






2-I—C


4


H


4






Prop-1-en-3-yl






1344




CH


3






2-I—C


4


H


4






(E)-1-Chloroprop-1-en-3-yl






1345




CH


3






2-I—C


4


H


4






Propyn-3-yl






1346




CH


3






2-I—C


4


H


4






3-Methyl-but-2-en-1-yl






1347




CH


3






3-I—C


4


H


4






H






1348




CH


3






3-I—C


4


H


4






CH


3








1349




CH


3






3-I—C


4


H


4






C


2


H


5









1350




CH


3






3-I—C


4


H


4






n-C


3


H


7








1351




CH


3






3-I—C


4


H


4






i-C


3


H


7








1352




CH


3






3-I—C


4


H


4






n-C


4


H


9








1353




CH


3






3-I—C


4


H


4






t-C


4


H


9








1354




CH


3






3-I—C


4


H


4






n-C


6


H


13








1355




CH


3






3-I—C


4


H


4






Prop-1-en-3-yl






1356




CH


3






3-I—C


4


H


4






(E)-1-Chloroprop-1-en-3-yl






1357




CH


3






3-I—C


4


H


4






Propyn-3-yl






1358




CH


3






3-I—C


4


H


4






3-Methyl-but-2-en-1-yl






1359




CH


3






4-I—C


4


H


4






H






1360




CH


3






4-I—C


4


H


4






CH


3








1361




CH


3






4-I—C


4


H


4






C


2


H


5









1362




CH


3






4-I—C


4


H


4






n-C


3


H


7








1363




CH


3






4-I—C


4


H


4






i-C


3


H


7








1364




CH


3






4-I—C


4


H


4






n-C


4


H


9








1365




CH


3






4-I—C


4


H


4






t-C


4


H


9








1366




CH


3






4-I—C


4


H


4






n-C


6


H


13








1367




CH


3






4-I—C


4


H


4






Prop-1-en-3-yl






1368




CH


3






4-I—C


4


H


4






(E)-1-Chloroprop-1-en-3-yl






1369




CH


3






4-I—C


4


H


4






Propyn-3-yl






1370




CH


3






4-I—C


4


H


4






3-Methyl-but-2-en-1-yl






1371




CH


3






2-CN—C


6


H


4






H






1372




CH


3






2-CN—C


6


H


4






CH


3








1373




CH


3






2-CN—C


6


H


4






C


2


H


5









1374




CH


3






2-CN—C


6


H


4






n-C


3


H


7








1375




CH


3






2-CN—C


6


H


4






i-C


3


H


7








1376




CH


3






2-CN—C


6


H


4






n-C


4


H


9








1377




CH


3






2-CN—C


6


H


4






t-C


4


H


9








1378




CH


3






2-CN—C


6


H


4






n-C


6


H


13








1379




CH


3






2-CN—C


6


H


4






Prop-1-en-3-yl






1380




CH


3






2-CN—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1381




CH


3






2-CN—C


6


H


4






Propyn-3-yl






1382




CH


3






2-CN—C


6


H


4






3-Methyl-but-2-en-1-yl






1383




CH


3






3-CN—C


6


H


4






H






1364




CH


3






3-CN—C


6


H


4






CH


3








1385




CH


3






3-CN—C


6


H


4






C


2


H


5









1386




CH


3






3-CN—C


6


H


4






n-C


3


H


7








1387




CH


3






3-CN—C


6


H


4






i-C


3


H


7








1388




CH


3






3-CN—C


6


H


4






n-C


4


H


9








1389




CH


3






3-CN—C


6


H


4






t-C


4


H


9








1390




CH


3






3-CN—C


6


H


4






n-C


6


H


13








1391




CH


3






3-CN—C


6


H


4






Prop-1-en-3-yl






1392




CH


3






3-CN—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1393




CH


3






3-CN—C


6


H


4






Propyn-3-yl






1394




CH


3






3-CN—C


6


H


4






3-Methyl-but-2-en-1-yl






1395




CH


3






4-CN—C


6


H


4






H






1396




CH


3






4-CN—C


6


H


4






CH


3








1397




CH


3






4-CN—C


6


H


4






C


2


H


5









1398




CH


3






4-CN—C


6


H


4






n-C


3


H


7








1399




CH


3






4-CN—C


6


H


4






i-C


3


H


7








1400




CH


3






4-CN—C


6


H


4






n-C


4


H


9








1401




CH


3






4-CN—C


6


H


4






t-C


4


H


9








1402




CH


3






4-CN—C


6


H


4






n-C


6


H


13








1403




CH


3






4-CN—C


6


H


4






Prop-1-en-3-yl






1404




CH


3






4-CN—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1405




CH


3






4-CN—C


6


H


4






Propyn-3-yl






1406




CH


3






4-CN—C


6


H


4






3-Methyl-but-2-en-1-yl






1407




CH


3






2-NO


2


—C


6


H


4






H






1408




CH


3






2-NO


2


—C


6


H


4






CH


3








1409




CH


3






2-NO


2


—C


6


H


4






C


2


H


5









1410




CH


3






2-NO


2


—C


6


H


4






n-C


3


H


7








1411




CH


3






2-NO


2


—C


6


H


4






i-C


3


H


7








1412




CH


3






2-NO


2


—C


6


H


4






n-C


4


H


9








1413




CH


3






2-NO


2


—C


6


H


4






t-C


4


H


9








1414




CH


3






2-NO


2


—C


6


H


4






n-C


6


H


13








1415




CH


3






2-NO


2


—C


6


H


4






Prop-1-en-3-yl






1416




CH


3






2-NO


2


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1417




CH


3






2-NO


2


—C


6


H


4






Propyn-3-yl






1418




CH


3






2-NO


2


—C


6


H


4






3-Methyl-but-2-en-1-yl






1419




CH


3






3-NO


2


—C


6


H


4






H






1420




CH


3






3-NO


2


—C


6


H


4






CH


3








1421




CH


3






3-NO


2


—C


6


H


4






C


2


H


5









1422




CH


3






3-NO


2


—C


6


H


4






n-C


3


H


7








1423




CH


3






3-NO


2


—C


6


H


4






i-C


3


H


7








1424




CH


3






3-NO


2


—C


6


H


4






n-C


4


H


9








1425




CH


3






3-NO


2


—C


6


H


4






t-C


4


H


9








1426




CH


3






3-NO


2


—C


6


H


4






n-C


6


H


13








1427




CH


3






3-NO


2


—C


6


H


4






Prop-1-en-3-yl






1428




CH


3






3-NO


2


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1429




CH


3






3-NO


2


—C


6


H


4






Propyn-3-yl






1430




CH


3






3-NO


2


—C


6


H


4






3-Methyl-but-2-en-1-yl






1431




CH


3






4-NO


2


—C


6


H


4






H






1432




CH


3






4-NO


2


—C


6


H


4






CH


3








1433




CH


3






4-NO


2


—C


6


H


4






C


2


H


5









1434




CH


3






4-NO


2


—C


6


H


4






n-C


3


H


7








1435




CH


3






4-NO


2


—C


6


H


4






i-C


3


H


7








1436




CH


3






4-NO


2


—C


6


H


4






n-C


4


H


9








1437




CH


3






4-NO


2


—C


6


H


4






t-C


4


H


9








1438




CH


3






4-NO


2


—C


6


H


4






n-C


6


H


13








1439




CH


3






4-NO


2


—C


6


H


4






Prop-1-en-3-yl






1440




CH


3






4-NO


2


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1441




CH


3






4-NO


2


—C


6


H


4






Propyn-3-yl






1442




CH


3






4-NO


2


—C


6


H


4






3-Methyl-but-2-en-1-yl






1443




CH


3






2-CH


3


—C


6


H


4






H






1444




CH


3






2-CH


3


—C


6


H


4






CH


3








1445




CH


3






2-CH


3


—C


6


H


4






C


2


H


5









1446




CH


3






2-CH


3


—C


6


H


4






n-C


3


H


7








1447




CH


3






2-CH


3


—C


6


H


4






i-C


3


H


7








1448




CH


3






2-CH


3


—C


6


H


4






n-C


4


H


9








1449




CH


3






2-CH


3


—C


6


H


4






t-C


4


H


9








1450




CH


3






2-CH


3


—C


6


H


4






n-C


6


H


13








1451




CH


3






2-CH


3


—C


6


H


4






Prop-1-en-3-yl






1452




CH


3






2-CH


3


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1453




CH


3






2-CH


3


—C


6


H


4






Propyn-3-yl






1454




CH


3






2-CH


3


—C


6


H


4






3-Methyl-but-2-en-1-yl






1455




CH


3






3-CH


3


—C


6


H


4






H






1456




CH


3






3-CH


3


—C


6


H


4






CH


3








1457




CH


3






3-CH


3


—C


6


H


4






C


2


H


5









1458




CH


3






3-CH


3


—C


6


H


4






n-C


3


H


7








1459




CH


3






3-CH


3


—C


6


H


4






i-C


3


H


7








1460




CH


3






3-CH


3


—C


6


H


4






n-C


4


H


9








1461




CH


3






3-CH


3


—C


6


H


4






t-C


4


H


9








1462




CH


3






3-CH


3


—C


6


H


4






n-C


6


H


13








1463




CH


3






3-CH


3


—C


6


H


4






Prop-1-en-3-yl






1464




CH


3






3-CH


3


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1465




CH


3






3-CH


3


—C


6


H


4






Propyn-3-yl






1466




CH


3






3-CH


3


—C


6


H


4






3-Methyl-but-2-en-1-yl






1467




CH


3






4-CH


3


—C


6


H


4






H






1468




CH


3






4-CH


3


—C


6


H


4






CH


3








1469




CH


3






4-CH


3


—C


6


H


4






C


2


H


5









1470




CH


3






4-CH


3


—C


6


H


4






n-C


3


H


7








1471




CH


3






4-CH


3


—C


6


H


4






i-C


3


H


7








1472




CH


3






4-CH


3


—C


6


H


4






n-C


4


H


9








1473




CH


3






4-CH


3


—C


6


H


4






t-C


4


H


9








1474




CH


3






4-CH


3


—C


6


H


4






n-C


6


H


13








1475




CH


3






4-CH


3


—C


6


H


4






Prop-1-en-3-yl






1476




CH


3






4-CH


3


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1477




CH


3






4-CH


3


—C


6


H


4






Propyn-3-yl






1478




CH


3






4-CH


3


—C


6


H


4






3-Methyl-but-2-en-1-yl






1479




CH


3






2,3-(CH


3


)


2


—C


6


H


3






H






1480




CH


3






2,3-(CH


3


)


2


—C


6


H


3






CH


3








1481




CH


3






2,3-(CH


3


)


2


—C


6


H


3






C


2


H


5









1482




CH


3






2,3-(CH


3


)


2


—C


6


H


3






n-C


3


H


7








1483




CH


3






2,3-(CH


3


)


2


—C


6


H


3






i-C


3


H


7








1484




CH


3






2,3-(CH


3


)


2


—C


6


H


3






n-C


4


H


9








1485




CH


3






2,3-(CH


3


)


2


—C


6


H


3






t-C


4


H


9








1486




CH


3






2,3-(CH


3


)


2


—C


6


H


3






n-C


6


H


13








1487




CH


3






2,3-(CH


3


)


2


—C


6


H


3






Prop-1-en-3-yl






1488




CH


3






2,3-(CH


3


)


2


—C


6


H


3






(E)-1-Chloroprop-1-en-3-yl






1489




CH


3






2,3-(CH


3


)


2


—C


6


H


3






Propyn-3-yl






1490




CH


3






2,3-(CH


3


)


2


—C


6


H


3






3-Methyl-but-2-en-1-yl






1491




CH


3






2,4-(CH


3


)


2


—C


6


H


3






H






1492




CH


3






2,4-(CH


3


)


2


—C


6


H


3






CH


3








1493




CH


3






2,4-(CH


3


)


2


—C


6


H


3






C


2


H


5









1494




CH


3






2,4-(CH


3


)


2


—C


6


H


3






n-C


3


H


7








1495




CH


3






2,4-(CH


3


)


2


—C


6


H


3






i-C


3


H


7








1496




CH


3






2,4-(CH


3


)


2


—C


6


H


3






n-C


4


H


9








1497




CH


3






2,4-(CH


3


)


2


—C


6


H


3






t-C


4


H


9








1498




CH


3






2,4-(CH


3


)


2


—C


6


H


3






n-C


6


H


13








1499




CH


3






2,4-(CH


3


)


2


—C


6


H


3






Prop-1-en-3-yl






1500




CH


3






2,4-(CH


3


)


2


—C


6


H


3






(E)-1-Chloroprop-1-en-3-yl






1501




CH


3






2,4-(CH


3


)


2


—C


6


H


3






Propyn-3-yl






1502




CH


3






2,4-(CH


3


)


2


—C


6


H


3






3-Methyl-but-2-en-1-yl






1503




CH


3






2,5-(CH


3


)


2


—C


6


H


3






H






1504




CH


3






2,5-(CH


3


)


2


—C


6


H


3






CH


3








1505




CH


3






2,5-(CH


3


)


2


—C


6


H


3






C


2


H


5









1506




CH


3






2,5-(CH


3


)


2


—C


6


H


3






n-C


3


H


7








1507




CH


3






2,5-(CH


3


)


2


—C


6


H


3






i-C


3


H


7








1508




CH


3






2,5-(CH


3


)


2


—C


6


H


3






n-C


4


H


9








1509




CH


3






2,5-(CH


3


)


2


—C


6


H


3






t-C


4


H


9








1510




CH


3






2,5-(CH


3


)


2


—C


6


H


3






n-C


6


H


13








1511




CH


3






2,5-(CH


3


)


2


—C


6


H


3






Prop-1-en-3-yl






1512




CH


3






2,5-(CH


3


)


2


—C


6


H


3






(E)-1-Chloroprop-1-en-3-yl






1513




CH


3






2,5-(CH


3


)


2


—C


6


H


3






Propyn-3-yl






1514




CH


3






2,5-(CH


3


)


2


—C


6


H


3






3-Methyl-but-2-en-1-yl






1515




CH


3






2,6-(CH


3


)


2


—C


6


H


3






H






1516




CH


3






2,6-(CH


3


)


2


—C


6


H


3






CH


3








1517




CH


3






2,6-(CH


3


)


2


—C


6


H


3






C


2


H


5









1518




CH


3






2,6-(CH


3


)


2


—C


6


H


3






n-C


3


H


7








1519




CH


3






2,6-(CH


3


)


2


—C


6


H


3






i-C


3


H


7








1520




CH


3






2,6-(CH


3


)


2


—C


6


H


3






n-C


4


H


9








1521




CH


3






2,6-(CH


3


)


2


—C


6


H


3






t-C


4


H


9








1522




CH


3






2,6-(CH


3


)


2


—C


6


H


3






n-C


6


H


13








1523




CH


3






2,6-(CH


3


)


2


—C


6


H


3






Prop-1-en-3-yl






1524




CH


3






2,6-(CH


3


)


2


—C


6


H


3






(E)-1-Chloroprop-1-en-3-yl






1525




CH


3






2,6-(CH


3


)


2


—C


6


H


3






Propyn-3-yl






1526




CH


3






2,6-(CH


3


)


2


—C


6


H


3






3-Methyl-but-2-en-1-yl






1527




CH


3






3,4-(CH


3


)


2


—C


6


H


3






H






1528




CH


3






3,4-(CH


3


)


2


—C


6


H


3






CH


3








1529




CH


3






3,4-(CH


3


)


2


—C


6


H


3






C


2


H


5









1530




CH


3






3,4-(CH


3


)


2


—C


6


H


3






n-C


3


H


7








1531




CH


3






3,4-(CH


3


)


2


—C


6


H


3






i-C


3


H


7








1532




CH


3






3,4-(CH


3


)


2


—C


6


H


3






n-C


4


H


9








1533




CH


3






3,4-(CH


3


)


2


—C


6


H


3






t-C


4


H


9








1534




CH


3






3,4-(CH


3


)


2


—C


6


H


3






n-C


6


H


13








1535




CH


3






3,4-(CH


3


)


2


—C


6


H


3






Prop-1-en-3-yl






1536




CH


3






3,4-(CH


3


)


2


—C


6


H


3






(E)-1-Chloroprop-1-en-3-yl






1537




CH


3






3,4-(CH


3


)


2


—C


6


H


3






Propyn-3-yl






1538




CH


3






3,4-(CH


3


)


2


—C


6


H


3






3-Methyl-but-2-en-1-yl






1539




CH


3






3,5-(CH


3


)


2


—C


6


H


3






H






1540




CH


3






3,5-(CH


3


)


2


—C


6


H


3






CH


3








1541




CH


3






3,5-(CH


3


)


2


—C


6


H


3






C


2


H


5









1542




CH


3






3,5-(CH


3


)


2


—C


6


H


3






n-C


3


H


7








1543




CH


3






3,5-(CH


3


)


2


—C


6


H


3






i-C


3


H


7








1544




CH


3






3,5-(CH


3


)


2


—C


6


H


3






n-C


4


H


9








1545




CH


3






3,5-(CH


3


)


2


—C


6


H


3






t-C


4


H


9








1546




CH


3






3,5-(CH


3


)


2


—C


6


H


3






n-C


6


H


13








1547




CH


3






3,5-(CH


3


)


2


—C


6


H


3






Prop-1-en-3-yl






1548




CH


3






3,5-(CH


3


)


2


—C


6


H


3






(E)-1-Chloroprop-1-en-3-yl






1549




CH


3






3,5-(CH


3


)


2


—C


6


H


3






Propyn-3-yl






1550




CH


3






3,5-(CH


3


)


2


—C


6


H


3






3-Methyl-but-2-en-1-yl






1551




CH


3






2-C


2


H


5


—C


6


H


4






H






1552




CH


3






2-C


2


H


5


—C


6


H


4






CH


3








1553




CH


3






2-C


2


H


5


—C


6


H


4






C


2


H


5









1554




CH


3






2-C


2


H


5


—C


6


H


4






n-C


3


H


7








1555




CH


3






2-C


2


H


5


—C


6


H


4






t-C


4


H


9








1556




CH


3






2-C


2


H


5


—C


6


H


4






n-C


6


H


13








1557




CH


3






2-C


2


H


5


—C


6


H


4






Prop-1-en-3-yl






1558




CH


3






2-C


2


H


5


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1559




CH


3






2-C


2


H


5


—C


6


H


4






Propyn-3-yl






1560




CH


3






2-C


2


H


5


—C


6


H


4






3-Methyl-but-2-en-1-yl






1561




CH


3






3-C


2


H


5


—C


6


H


4






H






1562




CH


3






3-C


2


H


5


—C


6


H


4






CH


3








1563




CH


3






3-C


2


H


5


—C


6


H


4






C


2


H


5








1564




CH


3






3-C


2


H


5


—C


6


H


4






n-C


3


H


7








1565




CH


3






3-C


2


H


5


—C


6


H


4






i-C


3


H


7








1566




CH


3






3-C


2


H


5


—C


6


H


4






n-C


4


H


9








1567




CH


3






3-C


2


H


5


—C


6


H


4






t-C


4


H


9








1568




CH


3






3-C


2


H


5


—C


6


H


4






n-C


6


H


13








1569




CH


3






3-C


2


H


5


—C


6


H


4






Prop-1-en-3-yl






1570




CH


3






3-C


2


H


5


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1571




CH


3






3-C


2


H


5


—C


6


H


4






Propyn-3-yl






1572




CH


3






3-C


2


H


5


—C


6


H


4






3-Methyl-but-2-en-1-yl






1573




CH


3






4-C


2


H


5


—C


6


H


4






H






1574




CH


3






4-C


2


H


5


—C


6


H


4






CH


3








1575




CH


3






4-C


2


H


5


—C


6


H


4






C


2


H


5









1576




CH


3






4-C


2


H


5


—C


6


H


4






n-C


3


H


7








1577




CH


3






4-C


2


H


5


—C


6


H


4






i-C


3


H


7








1578




CH


3






4-C


2


H


5


—C


6


H


4






n-C


4


H


9








1579




CH


3






4-C


2


H


5


—C


6


H


4






t-C


4


H


9








1580




CH


3






4-C


2


H


5


—C


6


H


4






n-C


6


H


13








1581




CH


3






4-C


2


H


5


—C


6


H


4






Prop-1-en-3-yl






1582




CH


3






4-C


2


H


5


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1583




CH


3






4-C


2


H


5


—C


6


H


4






Propyn-3-yl






1584




CH


3






4-C


2


H


5


—C


6


H


4






3-Methyl-but-2-en-1-yl






1585




CH


3






2-i-C


3


H


7


—C


6


H


4






H






1586




CH


3






2-i-C


3


H


7


—C


6


H


4






CH


3








1587




CH


3






2-i-C


3


H


7


—C


6


H


4






C


2


H


5









1588




CH


3






2-i-C


3


H


7


—C


6


H


4






n-C


3


H


7








1589




CH


3






2-i-C


3


H


7


—C


6


H


4






i-C


3


H


7








1590




CH


3






2-i-C


3


H


7


—C


6


H


4






n-C


4


H


9








1591




CH


3






2-i-C


3


H


7


—C


6


H


4






t-C


4


H


9








1592




CH


3






2-i-C


3


H


7


—C


6


H


4






n-C


6


H


13








1593




CH


3






2-i-C


3


H


7


—C


6


H


4






Prop-1-en-3-yl






1594




CH


3






2-i-C


3


H


7


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1595




CH


3






2-i-C


3


H


7


—C


6


H


4






Propyn-3-yl






1596




CH


3






2-i-C


3


H


7


—C


6


H


4






3-Methyl-but-2-en-1-yl






1597




CH


3






3-i-C


3


H


7


—C


6


H


4






H






1598




CH


3






3-i-C


3


H


7


—C


6


H


4






CH


3








1599




CH


3






3-i-C


3


H


7


—C


6


H


4






C


2


H


5









1600




CH


3






3-i-C


3


H


7


—C


6


H


4






n-C


3


H


7








1601




CH


3






3-i-C


3


H


7


—C


6


H


4






i-C


3


H


7








1602




CH


3






3-i-C


3


H


7


—C


6


H


4






n-C


4


H


9








1603




CH


3






3-i-C


3


H


7


—C


6


H


4






t-C


4


H


9








1604




CH


3






3-i-C


3


H


7


—C


6


H


4






n-C


6


H


13








1605




CH


3






3-i-C


3


H


7


—C


6


H


4






Prop-1-en-3-yl






1606




CH


3






3-i-C


3


H


7


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1607




CH


3






3-i-C


3


H


7


—C


6


H


4






Propyn-3-yl






1608




CH


3






3-i-C


3


H


7


—C


6


H


4






3-Methyl-but-2-en-1-yl






1609




CH


3






4-i-C


3


H


7


—C


6


H


4






H






1610




CH


3






4-i-C


3


H


7


—C


6


H


4






CH


3








1611




CH


3






4-i-C


3


H


7


—C


6


H


4






C


2


H


5








1612




CH


3






4-i-C


3


H


7


—C


6


H


4






n-C


3


H


7








1613




CH


3






4-i-C


3


H


7


—C


6


H


4






i-C


3


H


7








1614




CH


3






4-i-C


3


H


7


—C


6


H


4






n-C


4


H


9








1615




CH


3






4-i-C


3


H


7


—C


6


H


4






t-C


4


H


9








1616




CH


3






4-i-C


3


H


7


—C


6


H


4






n-C


6


H


13








1617




CH


3






4-i-C


3


H


7


—C


6


H


4






Prop-1-en-3-yl






1618




CH


3






4-i-C


3


H


7


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1619




CH


3






4-i-C


3


H


7


—C


6


H


4






Propyn-3-yl






1620




CH


3






4-i-C


3


H


7


—C


6


H


4






3-Methyl-but-2-en-1-yl






1621




CH


3






2-OH—C


6


H


4






H






1622




CH


3






2-OH—C


6


H


4






CH


3








1623




CH


3






2-OH—C


6


H


4






C


2


H


5








1624




CH


3






2-OH—C


6


H


4






n-C


3


H


7








1625




CH


3






2-OH—C


6


H


4






i-C


3


H


7








1626




CH


3






2-OH—C


6


H


4






n-C


4


H


9








1627




CH


3






2-OH—C


6


H


4






t-C


4


H


9








1628




CH


3






2-OH—C


6


H


4






n-C


6


H


13








1629




CH


3






2-OH—C


6


H


4






Prop-1-en-3-yl






1630




CH


3






2-OH—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1631




CH


3






2-OH—C


6


H


4






Propyn-3-yl






1632




CH


3






2-OH—C


6


H


4






3-Methyl-but-2-en-1-yl






1633




CH


3






3-OH—C


6


H


4






H






1634




CH


3






3-OH—C


6


H


4






CH


3








1635




CH


3






3-OH—C


6


H


4






C


2


H


5









1636




CH


3






3-OH—C


6


H


4






n-C


3


H


7








1637




CH


3






3-OH—C


6


H


4






i-C


3


H


7








1638




CH


3






3-OH—C


6


H


4






n-C


4


H


9








1639




CH


3






3-OH—C


6


H


4






t-C


4


H


9








1640




CH


3






3-OH—C


6


H


4






n-C


6


H


13








1641




CH


3






3-OH—C


6


H


4






Prop-1-en-3-yl






1642




CH


3






3-OH—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1643




CH


3






3-OH—C


6


H


4






Propyn-3-yl






1644




CH


3






3-OH—C


6


H


4






3-Methyl-but-2-en-1-yl






1645




CH


3






4-OH—C


6


H


4






H






1646




CH


3






4-OH—C


6


H


4






CH


3








1647




CH


3






4-OH—C


6


H


4






C


2


H


5









1648




CH


3






4-OH—C


6


H


4






n-C


3


H


7








1649




CH


3






4-OH—C


6


H


4






i-C


3


H


7








1650




CH


3






4-OH—C


6


H


4






n-C


4


H


9








1651




CH


3






4-OH—C


6


H


4






t-C


4


H


9








1652




CH


3






4-OH—C


6


H


4






n-C


6


H


13








1653




CH


3






4-OH—C


6


H


4






Prop-1-en-3-yl






1654




CH


3






4-OH—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1655




CH


3






4-OH—C


6


H


4






Propyn-3-yl






1656




CH


3






4-OH—C


6


H


4






3-Methyl-but-2-en-1-yl






1657




CH


3






2-OCH


3


—C


6


H


4






H






1658




CH


3






2-OCH


3


—C


6


H


4






CH


3








1659




CH


3






2-OCH


3


—C


6


H


4






C


2


H


5








1660




CH


3






2-OCH


3


—C


6


H


4






n-C


3


H


7








1661




CH


3






2-OCH


3


—C


6


H


4






i-C


3


H


7








1662




CH


3






2-OCH


3


—C


6


H


4






n-C


4


H


9








1663




CH


3






2-OCH


3


—C


6


H


4






t-C


4


H


9








1664




CH


3






2-OCH


3


—C


6


H


4






n-C


6


H


13








1665




CH


3






2-OCH


3


—C


6


H


4






Prop-1-en-3-yl






1666




CH


3






2-OCH


3


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1667




CH


3






2-OCH


3


—C


6


H


4






Propyn-3-yl






1668




CH


3






2-OCH


3


—C


6


H


4






3-Methyl-but-2-en-1-yl






1669




CH


3






3-OCH


3


—C


6


H


4






H






1670




CH


3






3-OCH


3


—C


6


H


4






CH


3








1671




CH


3






3-OCH


3


—C


6


H


4






C


2


H


5









1672




CH


3






3-OCH


3


—C


6


H


4






n-C


3


H


7








1673




CH


3






3-OCH


3


—C


6


H


4






i-C


3


H


7








1674




CH


3






3-OCH


3


—C


6


H


4






n-C


4


H


9








1675




CH


3






3-OCH


3


—C


6


H


4






t-C


4


H


9








1676




CH


3






3-OCH


3


—C


6


H


4






n-C


6


H


13








1677




CH


3






3-OCH


3


—C


6


H


4






Prop-1-en-3-yl






1678




CH


3






3-OCH


3


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1679




CH


3






3-OCH


3


—C


6


H


4






Propyn-3-yl






1680




CH


3






3-OCH


3


—C


6


H


4






3-Methyl-but-2-en-1-yl






1681




CH


3






4-OCH


3


—C


6


H


4






H






1682




CH


3






4-OCH


3


—C


6


H


4






CH


3








1683




CH


3






4-OCH


3


—C


6


H


4






C


2


H


5









1684




CH


3






4-OCH


3


—C


6


H


4






n-C


3


H


7








1685




CH


3






4-OCH


3


—C


6


H


4






i-C


3


H


7








1686




CH


3






4-OCH


3


—C


6


H


4






n-C


4


H


9








1687




CH


3






4-OCH


3


—C


6


H


4






t-C


4


H


9








1668




CH


3






4-OCH


3


—C


6


H


4






n-C


6


H


13








1689




CH


3






4-OCH


3


—C


6


H


4






Prop-1-en-3-yl






1690




CH


3






4-OCH


3


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1691




CH


3






4-OCH


3


—C


6


H


4






Propyn-3-yl






1692




CH


3






4-OCH


3


—C


6


H


4






3-Methyl-but-2-en-1-yl






1693




CH


3






2-OC


2


H


5


—C


6


H


4






H






1694




CH


3






2-OC


2


H


5


—C


6


H


4






CH


3








1695




CH


3






2-OC


2


H


5


—C


6


H


4






C


2


H


5









1696




CH


3






2-OC


2


H


5


—C


6


H


4






n-C


3


H


7








1697




CH


3






2-OC


2


H


5


—C


6


H


4






i-C


3


H


7








1698




CH


3






2-OC


2


H


5


—C


6


H


4






n-C


4


H


9








1699




CH


3






2-OC


2


H


5


—C


6


H


4






t-C


4


H


9








1700




CH


3






2-OC


2


H


5


—C


6


H


4






n-C


6


H


13








1701




CH


3






2-OC


2


H


5


—C


6


H


4






Prop-1-en-3-yl






1702




CH


3






2-OC


2


H


5


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1703




CH


3






2-OC


2


H


5


—C


6


H


4






Propyn-3-yl






1704




CH


3






2-OC


2


H


5


—C


6


H


4






3-Methyl-but-2-en-1-yl






1705




CH


3






3-OC


2


H


5


—C


6


H


4






H






1706




CH


3






3-OC


2


H


5


—C


6


H


4






CH


3








1707




CH


3






3-OC


2


H


5


—C


6


H


4






C


2


H


5









1708




CH


3






3-OC


2


H


5


—C


6


H


4






n-C


3


H


7








1709




CH


3






3-OC


2


H


5


—C


6


H


4






i-C


3


H


7








1710




CH


3






3-OC


2


H


5


—C


6


H


4






n-C


4


H


9








1711




CH


3






3-OC


2


H


5


—C


6


H


4






t-C


4


H


9








1712




CH


3






3-OC


2


H


5


—C


6


H


4






n-C


6


H


13








1713




CH


3






3-OC


2


H


5


—C


6


H


4






Prop-1-en-3-yl






1714




CH


3






3-OC


2


H


5


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1715




CH


3






3-OC


2


H


5


—C


6


H


4






Propyn-3-yl






1716




CH


3






3-OC


2


H


5


—C


6


H


4






3-Methyl-but-2-en-1-yl






1717




CH


3






4-OC


2


H


5


—C


6


H


4






H






1718




CH


3






4-OC


2


H


5


—C


6


H


4






CH


3








1719




CH


3






4-OC


2


H


5


—C


6


H


4






C


2


H


5









1720




CH


3






4-OC


2


H


5


—C


6


H


4






n-C


3


H


7








1721




CH


3






4-OC


2


H


5


—C


6


H


4






i-C


3


H


7








1722




CH


3






4-OC


2


H


5


—C


6


H


4






n-C


4


H


9








1723




CH


3






4-OC


2


H


5


—C


6


H


4






t-C


4


H


9








1724




CH


3






4-OC


2


H


5


—C


6


H


4






n-C


6


H


13








1725




CH


3






4-OC


2


H


5


—C


6


H


4






Prop-1-en-3-yl






1726




CH


3






4-OC


2


H


5


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1727




CH


3






4-OC


2


H


5


—C


6


H


4






Propyn-3-yl






1728




CH


3






4-OC


2


H


5


—C


6


H


4






3-Methyl-but-2-en-1-yl






1729




CH


3






2-O-(i-C


3


H


7


)—C


6


H


4






H






1730




CH


3






2-O-(i-C


3


H


7


)—C


6


H


4






CH


3








1731




CH


3






2-O-(i-C


3


H


7


)—C


6


H


4






C


2


H


5









1732




CH


3






2-O-(i-C


3


H


7


)—C


6


H


4






n-C


3


H


7








1733




CH


3






2-O-(i-C


3


H


7


)—C


6


H


4






i-C


3


H


7








1734




CH


3






2-O-(i-C


3


H


7


)—C


6


H


4






n-C


4


H


9








1735




CH


3






2-O-(i-C


3


H


7


)—C


6


H


4






t-C


4


H


9








1736




CH


3






2-O-(i-C


3


H


7


)—C


6


H


4






n-C


6


H


13








1737




CH


3






2-O-(i-C


3


H


7


)—C


6


H


4






Prop-1-en-3-yl






1738




CH


3






2-O-(i-C


3


H


7


)—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1739




CH


3






2-O-(i-C


3


H


7


)—C


6


H


4






Propyn-3-yl






1740




CH


3






2-O-(i-C


3


H


7


)—C


6


H


4






3-Methyl-but-2-en-1-yl






1741




CH


3






3-O-(i-C


3


H


7


)—C


6


H


4






H






1742




CH


3






3-O-(i-C


3


H


7


)—C


6


H


4






CH


3








1743




CH


3






3-O-(i-C


3


H


7


)—C


6


H


4






C


2


H


5









1744




CH


3






3-O-(i-C


3


H


7


)—C


6


H


4






n-C


3


H


7








1745




CH


3






3-O-(i-C


3


H


7


)—C


6


H


4






i-C


3


H


7








1746




CH


3






3-O-(i-C


3


H


7


)—C


6


H


4






n-C


4


H


9








1747




CH


3






3-O-(i-C


3


H


7


)—C


6


H


4






t-C


4


H


9








1748




CH


3






3-O-(i-C


3


H


7


)—C


6


H


4






n-C


6


H


13








1749




CH


3






3-O-(i-C


3


H


7


)—C


6


H


4






Prop-1-en-3-yl






1750




CH


3






3-O-(i-C


3


H


7


)—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1751




CH


3






3-O-(i-C


3


H


7


)—C


6


H


4






Propyn-3-yl






1752




CH


3






3-O-(i-C


3


H


7


)—C


6


H


4






3-Methyl-but-2-en-1-yl






1753




CH


3






4-O-(i-C


3


H


7


)—C


6


H


4






H






1754




CH


3






4-O-(i-C


3


H


7


)—C


6


H


4






CH


3








1755




CH


3






4-O-(i-C


3


H


7


)—C


6


H


4






C


2


H


5









1756




CH


3






4-O-(i-C


3


H


7


)—C


6


H


4






n-C


3


H


7








1757




CH


3






4-O-(i-C


3


H


7


)—C


6


H


4






i-C


3


H


7








1758




CH


3






4-O-(i-C


3


H


7


)—C


6


H


4






n-C


4


H


9








1759




CH


3






4-O-(i-C


3


H


7


)—C


6


H


4






t-C


4


H


9








1760




CH


3






4-O-(i-C


3


H


7


)—C


6


H


4






n-C


6


H


13








1761




CH


3






4-O-(i-C


3


H


7


)—C


6


H


4






Prop-1-en-3-yl






1762




CH


3






4-O-(i-C


3


H


7


)—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1763




CH


3






4-O-(i-C


3


H


7


)—C


6


H


4






Propyn-3-yl






1764




CH


3






4-O-(i-C


3


H


7


)—C


6


H


4






3-Methyl-but-2-en-1-yl






1765




CH


3






2-O-(t-C


4


H


9


)—C


6


H


4






H






1766




CH


3






2-O-(t-C


4


H


9


)—C


6


H


4






CH


3








1767




CH


3






2-O-(t-C


4


H


9


)—C


6


H


4






C


2


H


5









1768




CH


3






2-O-(t-C


4


H


9


)—C


6


H


4






n-C


3


H


7








1769




CH


3






2-O-(t-C


4


H


9


)—C


6


H


4






i-C


3


H


7








1770




CH


3






2-O-(t-C


4


H


9


)—C


6


H


4






n-C


4


H


9








1771




CH


3






2-O-(t-C


4


H


9


)—C


6


H


4






t-C


4


H


9








1772




CH


3






2-O-(t-C


4


H


9


)—C


6


H


4






n-C


6


H


13








1773




CH


3






2-O-(t-C


4


H


9


)—C


6


H


4






Prop-1-en-3-yl






1774




CH


3






2-O-(t-C


4


H


9


)—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1775




CH


3






2-O-(t-C


4


H


9


)—C


6


H


4






Propyn-3-yl






1776




CH


3






2-O-(t-C


4


H


9


)—C


6


H


4






3-Methyl-but-2-en-1-yl






1777




CH


3






3-O-(t-C


4


H


9


)—C


6


H


4






H






1778




CH


3






3-O-(t-C


4


H


9


)—C


6


H


4






CH


3








1779




CH


3






3-O-(t-C


4


H


9


)—C


6


H


4






C


2


H


5









1780




CH


3






3-O-(t-C


4


H


9


)—C


6


H


4






n-C


3


H


7








1781




CH


3






3-O-(t-C


4


H


9


)—C


6


H


4






i-C


3


H


7








1782




CH


3






3-O-(t-C


4


H


9


)—C


6


H


4






n-C


4


H


9








1783




CH


3






3-O-(t-C


4


H


9


)—C


6


H


4






t-C


4


H


9








1784




CH


3






3-O-(t-C


4


H


9


)—C


6


H


4






n-C


6


H


13








1785




CH


3






3-O-(t-C


4


H


9


)—C


6


H


4






Prop-1-en-3-yl






1786




CH


3






3-O-(t-C


4


H


9


)—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1787




CH


3






3-O-(t-C


4


H


9


)—C


6


H


4






Propyn-3-yl






1788




CH


3






3-O-(t-C


4


H


9


)—C


6


H


4






3-Methyl-but-2-en-1-yl






1789




CH


3






4-O-(t-C


4


H


9


)—C


6


H


4






H






1790




CH


3






4-O-(t-C


4


H


9


)—C


6


H


4






CH


3








1791




CH


3






4-O-(t-C


4


H


9


)—C


6


H


4






C


2


H


5









1792




CH


3






4-O-(t-C


4


H


9


)—C


6


H


4






n-C


3


H


7








1793




CH


3






4-O-(t-C


4


H


9


)—C


6


H


4






i-C


3


H


7








1794




CH


3






4-O-(t-C


4


H


9


)—C


6


H


4






n-C


4


H


9








1795




CH


3






4-O-(t-C


4


H


9


)—C


6


H


4






t-C


4


H


9








1796




CH


3






4-O-(t-C


4


H


9


)—C


6


H


4






n-C


6


H


13








1797




CH


3






4-O-(t-C


4


H


9


)—C


6


H


4






Prop-1-en-3-yl






1798




CH


3






4-O-(t-C


4


H


9


)—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1799




CH


3






4-O-(t-C


4


H


9


)—C


6


H


4






Propyn-3-yl






1800




CH


3






4-O-(t-C


4


H


9


)—C


6


H


4






3-Methyl-but-2-en-1-yl






1801




CH


3






2-CF


3


—C


6


H


4






H






1802




CH


3






2-CF


3


—C


6


H


4






CH


3








1803




CH


3






2-CF


3


—C


6


H


4






C


2


H


5









1804




CH


3






2-CF


3


—C


6


H


4






n-C


3


H


7








1805




CH


3






2-CF


3


—C


6


H


4






i-C


3


H


7








1806




CH


3






2-CF


3


—C


6


H


4






n-C


4


H


9








1807




CH


3






2-CF


3


—C


6


H


4






t-C


4


H


9








1808




CH


3






2-CF


3


—C


6


H


4






n-C


6


H


13








1809




CH


3






2-CF


3


—C


6


H


4






Prop-1-en-3-yl






1810




CH


3






2-CF


3


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1811




CH


3






2-CF


3


—C


6


H


4






Propyn-3-yl






1812




CH


3






2-CF


3


—C


6


H


4






3-Methyl-but-2-en-1-yl






1813




CH


3






3-CF


3


—C


6


H


4






H






1814




CH


3






3-CF


3


—C


6


H


4






CH


3








1815




CH


3






3-CF


3


—C


6


H


4






C


2


H


5









1816




CH


3






3-CF


3


—C


6


H


4






n-C


3


H


7








1817




CH


3






3-CF


3


—C


6


H


4






i-C


3


H


7








1818




CH


3






3-CF


3


—C


6


H


4






n-C


4


H


9








1819




CH


3






3-CF


3


—C


6


H


4






t-C


4


H


9








1820




CH


3






3-CF


3


—C


6


H


4






n-C


6


H


13








1821




CH


3






3-CF


3


—C


6


H


4






Prop-1-en-3-yl






1822




CH


3






3-CF


3


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1823




CH


3






3-CF


3


—C


6


H


4






Propyn-3-yl






1824




CH


3






3-CF


3


—C


6


H


4






3-Methyl-but-2-en-1-yl






1825




CH


3






4-CF


3


—C


6


H


4






H






1826




CH


3






4-CF


3


—C


6


H


4






CH


3








1827




CH


3






4-CF


3


—C


6


H


4






C


2


H


5









1828




CH


3






4-CF


3


—C


6


H


4






n-C


3


H


7








1829




CH


3






4-CF


3


—C


6


H


4






i-C


3


H


7








1830




CH


3






4-CF


3


—C


6


H


4






n-C


4


H


9








1831




CH


3






4-CF


3


—C


6


H


4






t-C


4


H


9








1832




CH


3






4-CF


3


—C


6


H


4






n-C


6


H


13








1833




CH


3






4-CF


3


—C


6


H


4






Prop-1-en-3-yl






1834




CH


3






4-CF


3


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1835




CH


3






4-CF


3


—C


6


H


4






Propyn-3-yl






1836




CH


3






4-CF


3


—C


6


H


4






3-Methyl-but-2-en-1-yl






1837




CH


3






2-NH


2


—C


6


H


4






H






1838




CH


3






2-NH


2


—C


6


H


4






CH


3








1839




CH


3






2-NH


2


—C


6


H


4






C


2


H


5









1340




CH


3






2-NH


2


—C


6


H


4






n-C


3


H


7








1841




CH


3






2-NH


2


—C


6


H


4






i-C


3


H


7








1842




CH


3






2-NH


2


—C


6


H


4






n-C


4


H


9








1843




CH


3






2-NH


2


—C


6


H


4






t-C


4


H


9








1844




CH


3






2-NH


2


—C


6


H


4






n-C


6


H


13








1845




CH


3






2-NH


2


—C


6


H


4






Prop-1-en-3-yl






1846




CH


3






2-NH


2


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1847




CH


3






2-NH


2


—C


6


H


4






Propyn-3-yl






1848




CH


3






2-NH


2


—C


6


H


4






3-Methyl-but-2-en-1-yl






1849




CH


3






3-NH


2


—C


6


H


4






H






1850




CH


3






3-NH


2


—C


6


H


4






CH


3








1851




CH


3






3-NH


2


—C


6


H


4






C


2


H


5









1852




CH


3






3-NH


2


—C


6


H


4






n-C


3


H


7








1853




CH


3






3-NH


2


—C


6


H


4






i-C


3


H


7








1854




CH


3






3-NH


2


—C


6


H


4






n-C


4


H


9








1855




CH


3






3-NH


2


—C


6


H


4






t-C


4


H


9








1856




CH


3






3-NH


2


—C


6


H


4






n-C


6


H


13








1857




CH


3






3-NH


2


—C


6


H


4






Prop-1-en-3-yl






1858




CH


3






3-NH


2


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1859




CH


3






3-NH


2


—C


6


H


4






Propyn-3-yl






1860




CH


3






3-NH


2


—C


6


H


4






3-Methyl-but-2-en-1-yl






1861




CH


3






4-NH


2


—C


6


H


4






H






1862




CH


3






4-NH


2


—C


6


H


4






CH


3








1863




CH


3






4-NH


2


—C


6


H


4






C


2


H


5









1864




CH


3






4-NH


2


—C


6


H


4






n-C


3


H


7








1865




CH


3






4-NH


2


—C


6


H


4






i-C


3


H


7








1866




CH


3






4-NH


2


—C


6


H


4






n-C


4


H


9








1867




CH


3






4-NH


2


—C


6


H


4






t-C


4


H


9








1868




CH


3






4-NH


2


—C


6


H


4






n-C


6


H


13








1869




CH


3






4-NH


2


—C


6


H


4






Prop-1-en-3-yl






1870




CH


3






4-NH


2


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1871




CH


3






4-NH


2


—C


6


H


4






Propyn-3-yl






1872




CH


3






4-NH


2


—C


6


H


4






3-Methyl-but-2-en-1-yl






1873




CH


3






2-NMe


2


—C


6


H


4






H






1874




CH


3






2-NMe


2


—C


6


H


4






CH


3








1875




CH


3






2-NMe


2


—C


6


H


4






C


2


H


5








1876




CH


3






2-NMe


2


—C


6


H


4






n-C


3


H


7








1877




CH


3






2-NMe


2


—C


6


H


4






i-C


3


H


7








1878




CH


3






2-NMe


2


—C


6


H


4






n-C


4


H


9








1879




CH


3






2-NMe


2


—C


6


H


4






t-C


4


H


9








1880




CH


3






2-NMe


2


—C


6


H


4






n-C


6


H


13








1881




CH


3






2-NMe


2


—C


6


H


4






Prop-1-en-3-yl






1882




CH


3






2-NMe


2


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1883




CH


3






2-NMe


2


—C


6


H


4






Propyn-3-yl






1884




CH


3






2-NMe


2


—C


6


H


4






3-Methyl-but-2-en-1-yl






1885




CH


3






3-NMe


2


—C


6


H


4






H






1886




CH


3






3-NMe


2


—C


6


H


4






CH


3








1887




CH


3






3-NMe


2


—C


6


H


4






C


2


H


5








1888




CH


3






3-NMe


2


—C


6


H


4






n-C


3


H


7








1889




CH


3






3-NMe


2


—C


6


H


4






i-C


3


H


7








1890




CH


3






3-NMe


2


—C


6


H


4






n-C


4


H


9








1891




CH


3






3-NMe


2


—C


6


H


4






t-C


4


H


9








1892




CH


3






3-NMe


2


—C


6


H


4






n-C


6


H


13








1893




CH


3






3-NMe


2


—C


6


H


4






Prop-1-en-3-yl






1894




CH


3






3-NMe


2


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1895




CH


3






3-NMe


2


—C


6


H


4






Propyn-3-yl






1896




CH


3






3-NMe


2


—C


6


H


4






3-Methyl-but-2-en-1-yl






1897




CH


3






4-NMe


2


—C


6


H


4






H






1898




CH


3






4-NMe


2


—C


6


H


4






CH


3








1899




CH


3






4-NMe


2


—C


6


H


4






C


2


H


5









1900




CH


3






4-NMe


2


—C


6


H


4






n-C


3


H


7








1901




CH


3






4-NMe


2


—C


6


H


4






i-C


3


H


7








1902




CH


3






4-NMe


2


—C


6


H


4






n-C


4


H


9








1903




CH


3






4-NMe


2


—C


6


H


4






t-C


4


H


9








1904




CH


3






4-NMe


2


—C


6


H


4






n-C


6


H


13








1905




CH


3






4-NMe


2


—C


6


H


4






Prop-1-en-3-yl






1906




CH


3






4-NMe


2


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1907




CH


3






4-NMe


2


—C


6


H


4






Propyn-3-yl






1908




CH


3






4-NMe


2


—C


6


H


4






3-Methyl-but-2-en-1-yl






1909




CH


3






2-Aminothiocarbo-




H








nyl-C


6


H


4








1910




CH


3






2-Aminothiocarbo-




CH


3










nyl-C


6


H


4








1911




CH


3






2-Aminothiocarbo-




C


2


H


5










nyl-C


6


H


4








1912




CH


3






2-Aminothiocarbo-




n-C


3


H


7










nyl-C


6


H


4








1913




CH


3






2-Aminothiocarbo-




i-C


3


H


7










nyl-C


6


H


4








1914




CH


3






2-Aminothiocarbo-




n-C


4


H


9










nyl-C


6


H


4








1915




CH


3






2-Aminothiocarbo-




t-C


4


H


9










nyl-C


6


H


4








1916




CH


3






2-Aminothiocarbo-




n-C


6


H


13










nyl-C


6


H


4








1917




CH


3






2-Aminothiocarbo-




Prop-1-en-3-yl








nyl-C


6


H


4








1918




CH


3






2-Aminothiocarbo-




(E)-1-Chloroprop-1-en-3-yl








nyl-C


6


H


4








1919




CH


3






2-Aminothiocarbo-




Propyn-3-yl








nyl-C


6


H


4








1920




CH


3






2-Aminothiocarbo-




3-Methyl-but-2-en-1-yl








nyl-C


6


H


4








1921




CH


3






3-Aminothiocarbo-




H








nyl-C


6


H


4








1922




CH


3






3-Aminothiocarbo-




CH


3










nyl-C


6


H


4








1923




CH


3






3-Aminothiocarbo-




C


2


H


5











nyl-C


6


H


4








1924




CH


3






3-Aminothiocarbo-




n-C


3


H


7










nyl-C


6


H


4








1925




CH


3






3-Aminothiocarbo-




i-C


3


H


7










nyl-C


6


H


4








1926




CH


3






3-Aminothiocarbo-




n-C


4


H


9










nyl-C


6


H


4








1927




CH


3






3-Aminothiocarbo-




t-C


4


H


9










nyl-C


6


H


4








1928




CH


3






3-Aminothiocarbo-




n-C


6


H


13










nyl-C


6


H


4








1929




CH


3






3-Aminothiocarbo-




Prop-1-en-3-yl








nyl-C


6


H


4








1930




CH


3






3-Aminothiocarbo-




(E)-1-Chloroprop-1-en-3-yl








nyl-C


6


H


4








1931




CH


3






3-Aminothiocarbo-




Propyn-3-yl








nyl-C


6


H


4








1932




CH


3






3-Aminothiocarbo-




3-Methyl-but-2-en-1-yl








nyl-C


6


H


4








1933




CH


3






4-Aminothiocarbo-




H








nyl-C


6


H


4








1934




CH


3






4-Aminothiocarbo-




CH


3










nyl-C


6


H


4








1935




CH


3






4-Aminothiocarbo-




C


2


H


5










nyl-C


6


H


4








1936




CH


3






4-Aminothiocarbo-




n-C


3


H


7










nyl-C


6


H


4








1937




CH


3






4-Aminothiocarbo-




i-C


3


H


7










nyl-C


6


H


4








1938




CH


3






4-Aminothiocarbo-




n-C


4


H


9










nyl-C


6


H


4








1939




CH


3






4-Aminothiocarbo-




t-C


4


H


9










nyl-C


6


H


4








1940




CH


3






4-Aminothiocarbo-




n-C


6


H


13










nyl-C


6


H


4








1941




CH


3






4-Aminothiocarbo-




Prop-1-en-3-yl








nyl-C


6


H


4








1942




CH


3






4-Aminothiocarbo-




(E)-1-Chloroprop-1-en-3-yl








nyl-C


6


H


4








1943




CH


3






4-Aminothiocarbo-




Propyn-3-yl








nyl-C


6


H


4








1944




CH


3






4-Aminothiocarbo-




3-Methyl-but-2-en-1-yl








nyl-C


6


H


4








1945




CH


3






2-OCF


3


—C


6


H


4






H






1946




CH


3






2-OCF


3


—C


6


H


4






CH


3








1947




CH


3






2-OCF


3


—C


6


H


4






C


2


H


5








1948




CH


3






2-OCF


3


—C


6


H


4






n-C


3


H


7








1949




CH


3






2-OCF


3


—C


6


H


4






i-C


3


H


7








1950




CH


3






2-OCF


3


—C


6


H


4






n-C


4


H


9








1951




CH


3






2-OCF


3


—C


6


H


4






t-C


4


H


9








1952




CH


3






2-OCF


3


—C


6


H


4






n-C


6


H


13








1953




CH


3






2-C


2


H


5


—C


6


H


4






i-C


3


H


7








1954




CH


3






2-C


2


H


5


—C


6


H


4






n-C


4


H


9








1955




CH


3






2-OCF


3


—C


6


H


4






Prop-1-en-3-yl






1956




CH


3






2-OCF


3


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1957




CH


3






2-OCF


3


—C


6


H


4






Propyn-3-yl






1958




CH


3






2-OCF


3


—C


6


H


4






3-Methyl-but-2-en-1-yl






1959




CH


3






3-OCF


3


—C


6


H


4






H






1960




CH


3






3-OCF


3


—C


6


H


4






CH


3








1961




CH


3






3-OCF


3


—C


6


H


4






C


2


H


5








1962




CH


3






3-OCF


3


—C


6


H


4






n-C


3


H


7








1963




CH


3






3-OCF


3


—C


6


H


4






i-C


3


H


7








1964




CH


3






3-OCF


3


—C


6


H


4






n-C


4


H


9








1965




CH


3






3-OCF


3


—C


6


H


4






t-C


4


H


9








1966




CH


3






3-OCF


3


—C


6


H


4






n-C


6


H


13








1967




CH


3






3-OCF


3


—C


6


H


4






Prop-1-en-3-yl






1968




CH


3






3-OCF


3


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1969




CH


3






3-OCF


3


—C


6


H


4






Propyn-3-yl






1970




CH


3






3-OCF


3


—C


6


H


4






3-Methyl-but-2-en-1-yl






1971




CH


3






4-OCF


3


—C


6


H


4






H






1972




CH


3






4-OCF


3


—C


6


H


4






CH


3








1973




CH


3






4-OCF


3


—C


6


H


4






C


2


H


5








1974




CH


3






4-OCF


3


—C


6


H


4






n-C


3


H


7








1975




CH


3






4-OCF


3


—C


6


H


4






i-C


3


H


7








1976




CH


3






4-OCF


3


—C


6


H


4






n-C


4


H


9








1977




CH


3






4-OCF


3


—C


6


H


4






t-C


4


H


9








1978




CH


3






4-OCF


3


—C


6


H


4






n-C


6


H


13








1979




CH


3






4-OCF


3


—C


6


H


4






Prop-1-en-3-yl






1980




CH


3






4-OCF


3


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1981




CH


3






4-OCF


3


—C


6


H


4






Propyn-3-yl






1982




CH


3






4-OCF


3


—C


6


H


4






3-Methyl-but-2-en-1-yl






1983




CH


3






2-SCH


3


—C


6


H


4






H






1984




CH


3






2-SCH


3


—C


6


H


4






CH


3








1985




CH


3






2-SCH


3


—C


6


H


4






C


2


H


5









1986




CH


3






2-SCH


3


—C


6


H


4






n-C


3


H


7








1987




CH


3






2-SCH


3


—C


6


H


4






i-C


3


H


7








1988




CH


3






2-SCH


3


—C


6


H


4






n-C


4


H


9








1989




CH


3






2-SCH


3


—C


6


H


4






t-C


4


H


9








1990




CH


3






2-SCH


3


—C


6


H


4






n-C


6


H


13








1991




CH


3






2-SCH


3


—C


6


H


4






Prop-1-en-3-yl






1992




CH


3






2-SCH


3


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






1993




CH


3






2-SCH


3


—C


6


H


4






Propyn-3-yl






1994




CH


3






2-SCH


3


—C


6


H


4






3-Methyl-but-2-en-1-yl






1995




CH


3






3-SCH


3


—C


6


H


4






H






1996




CH


3






3-SCH


3


—C


6


H


4






CH


3








1997




CH


3






3-SCH


3


—C


6


H


4






C


2


H


5









1998




CH


3






3-SCH


3


—C


6


H


4






n-C


3


H


7








1999




CH


3






3-SCH


3


—C


6


H


4






i-C


3


H


7








2000




CH


3






3-SCH


3


—C


6


H


4






n-C


4


H


9








2001




CH


3






3-SCH


3


—C


6


H


4






t-C


4


H


9








2002




CH


3






3-SCH


3


—C


6


H


4






n-C


6


H


13








2003




CH


3






3-SCH


3


—C


6


H


4






Prop-1-en-3-yl






2004




CH


3






3-SCH


3


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






2005




CH


3






3-SCH


3


—C


6


H


4






Propyn-3-yl






2006




CH


3






3-SCH


3


—C


6


H


4






3-Methyl-but-2-en-1-yl






2007




CH


3






4-SCH


3


—C


6


H


4






H






2008




CH


3






4-SCH


3


—C


6


H


4






CH


3








2009




CH


3






4-SCH


3


—C


6


H


4






C


2


H


5









2010




CH


3






4-SCH


3


—C


6


H


4






n-C


3


H


7








2011




CH


3






4-SCH


3


—C


6


H


4






i-C


3


H


7








2012




CH


3






4-SCH


3


—C


6


H


4






n-C


4


H


9








2013




CH


3






4-SCH


3


—C


6


H


4






t-C


4


H


9








2014




CH


3






4-SCH


3


—C


6


H


4






n-C


6


H


13








2015




CH


3






4-SCH


3


—C


6


H


4






Prop-1-en-3-yl






2016




CH


3






4-SCH


3


—C


6


H


4






(E)-1-Chloroprop-1-en-3-yl






2017




CH


3






4-SCH


3


—C


6


H


4






Propyn-3-yl






2018




CH


3






4-SCH


3


—C


6


H


4






3-Methyl-but-2-en-1-yl






2019




CH


3






2-Methyl-




H








sulfonyl-C


6


H


4








2020




CH


3






2-Methyl-




CH


3










sulfonyl-C


6


H


4








2021




CH


3






2-Methyl-




C


2


H


5










sulfonyl-C


6


H


4








2022




CH


3






2-Methyl-




n-C


3


H


7










sulfonyl-C


6


H


4








2023




CH


3






2-Methyl-




i-C


3


H


7










sulfonyl-C


6


H


4








2024




CH


3






2-Methyl-




n-C


4


H


9










sulfonyl-C


6


H


4








2025




CH


3






2-Methyl-




t-C


4


H


9










sulfonyl-C


6


H


4








2026




CH


3






2-Methyl-




n-C


6


H


13










sulfonyl-C


6


H


4








2027




CH


3






2-Methyl-




Prop-1-en-3-yl








sulfonyl-C


6


H


4








2028




CH


3






2-Methyl-




(E)-1-Chloroprop-1-en-3-yl








sulfonyl-C


6


H


4








2029




CH


3






2-Methyl-




Propyn-3-yl








sulfonyl-C


6


H


4








2030




CH


3






2-Methyl-




3-Methyl-but-2-en-1-yl








sul fonyl-C


6


H


4








2031




CH


3






3-Methyl-




H








sulfonyl-C


6


H


4








2032




CH


3






3-Methyl-




CH


3










sulfonyl-C


6


H


4








2033




CH


3






3-Methyl-




C


2


H


5










sulfonyl-C


6


H


4








2034




CH


3






3-Methyl-




n-C


3


H


7










sulfonyl-C


6


H


4








2035




CH


3






3-Methyl-




i-C


3


H


7










sulfonyl-C


6


H


4








2036




CH


3






3-Methyl-




n-C


4


H


9










sulfonyl-C


6


H


4








2037




CH


3






3-Methyl-




t-C


4


H


9










sulfonyl-C


6


H


4








2038




CH


3






3-Methyl-




n-C


6


H


13










sulfonyl-C


6


H


4








2039




CH


3






3-Methyl-




Prop-1-en-3-yl








sulfonyl-C


6


H


4








2040




CH


3






3-Methyl-




(E)-1-Chloroprop-1-en-3-yl








sulfonyl-C


6


H


4








2041




CH


3






3-Methyl-




Propyn-3-yl








sulfonyl-C


6


H


4








2042




CH


3






3-Methyl-




3-Methyl-but-2-en-1-yl








sulfonyl-C


6


H


4








2043




CH


3






4-Methyl-




H








sulfonyl-C


6


H


4








2044




CH


3






4-Methyl-




CH


3










sulfonyl-C


6


H


4








2045




CH


3






4-Methyl-




C


2


H


5










sulfonyl-C


6


H


4








2046




CH


3






4-Methyl-




n-C


3


H


7










sulfonyl-C


6


H


4








2047




CH


3






4-Methyl-




i-C


3


H


7










sulfonyl-C


6


H


4








2048




CH


3






4-Methyl-




n-C


4


H


9










sulfonyl-C


6


H


4








2049




CH


3






4-Methyl-




t-C


4


H


9










sulfonyl-C


6


H


4








2050




CH


3






4-Methyl-




n-C


6


H


13










sulfonyl-C


6


H


4








2051




CH


3






4-Methyl-




Prop-1-en-3-yl








sulfonyl-C


6


H


4








2052




CH


3






4-Methyl-




(E)-1-Chloroprop-1-en-3-yl








sulfonyl-C


6


H


4








2053




CH


3






4-Methyl-




Propyn-3-yl








sulfonyl-C


6


H


4








2054




CH


3






4-Methyl-




3-Methyl-but-2-en-1-yl








sulfonyl-C


6


H


4








2055




CH


3






2-Methoxycarbo-




H








nyl-C


6


H


4








2056




CH


3






2-Methoxycarbo-




CH


3










nyl-C


6


H


4








2057




CH


3






2-Methoxycarbo-




C


2


H


5










nyl-C


6


H


4








2058




CH


3






2-Methoxycarbo-




n-C


3


H


7










nyl-C


6


H


4








2059




CH


3






2-Methoxycarbo-




i-C


3


H


7










nyl-C


6


H


4








2060




CH


3






2-Methoxycarbo-




n-C


4


H


9










nyl-C


6


H


4








2061




CH


3






2-Methoxycarbo-




t-C


4


H


9










nyl-C


6


H


4








2062




CH


3






2-Methoxycarbo-




n-C


6


H


13










nyl-C


6


H


4








2063




CH


3






2-Methoxycarbo-




Prop-1-en-3-yl








nyl-C


6


H


4








2064




CH


3






2-Methoxycarbo-




(E)-1-Chloroprop-1-en-3-yl








nyl-C


6


H


4








2065




CH


3






2-Methoxycarbo-




Propyn-3-yl








nyl-C


6


H


4








2066




CH


3






2-Methoxycarbo-




3-Methyl-but-2-en-1-yl








nyl-C


6


H


4








2067




CH


3






3-Methoxycarbo-




H








nyl-C


6


H


4








2068




CH


3






3-Methoxycarbo-




CH


3










nyl-C


6


H


4








2069




CH


3






3-Methoxycarbo-




C


2


H


5











nyl-C


6


H


4








2070




CH


3






3-Methoxycarbo-




n-C


3


H


7










nyl-C


6


H


4








2071




CH


3






3-Methoxycarbo-




i-C


3


H


7










nyl-C


6


H


4








2072




CH


3






3-Methoxycarbo-




n-C


4


H


9










nyl-C


6


H


4








2073




CH


3






3-Methoxycarbo-




t-C


4


H


9










nyl-C


6


H


4








2074




CH


3






3-Methoxycarbo-




n-C


6


H


13










nyl-C


6


H


4








2075




CH


3






3-Methoxycarbo-




Prop-1-en-3-yl








nyl-C


6


H


4








2076




CH


3






3-Methoxycarbo-




(E)-1-Chloroprop-1-en-3-yl








nyl-C


6


H


4








2077




CH


3






3-Methoxycarbo-




Propyn-3-yl








nyl-C


6


H


4








2078




CH


3






3-Methoxycarbo




3-Methyl-but-2-en-1-yl








nyl-C


6


H


4








2079




CH


3






4-Methoxycarbo-




H








nyl-C


6


H


4








2080




CH


3






4-Methoxycarbo-




CH


3










nyl-C


6


H


4








2081




CH


3






4-Methoxycarbo-




C


2


H


5










nyl-C


6


H


4








2082




CH


3






4-Methoxycarbo-




n-C


3


H


7










nyl-C


6


H


4








2083




CH


3






4-Methoxycarbo-




i-C


3


H


7










nyl-C


6


H


4








2084




CH


3






4-Methoxycarbo-




n-C


4


H


9










nyl-C


6


H


4








2085




CH


3






4-Methoxycarbo-




t-C


4


H


9










nyl-C


6


H


4








2086




CH


3






4-Methoxycarbo-




n-C


6


H


13










nyl-C


6


H


4








2087




CH


3






4-Methoxycarbo-




Prop-1-en-3-yl








nyl-C


6


H


4








2088




CH


3






4-Methoxycarbo-




(E)-1-Chloroprop-1-en-3-yl








nyl-C


6


H


4








2089




CH


3






4-Methoxycarbo-




Propyn-3-yl








nyl-C


6


H


4








2090




CH


3






4-Methoxycarbo-




3-Methyl-but-2-en-1-yl








nyl-C


6


H


4








2091




CH


3






2-Ethoxy-




H








carbonyl-C


6


H


4








2092




CH


3






2-Ethoxy-




CH


3










carbonyl-C


6


H


4








2093




CH


3






2-Ethoxy-




C


2


H


5










carbonyl-C


6


H


4








2094




CH


3






2-Ethoxy-




n-C


3


H


7










carbonyl-C


6


H


4








2095




CH


3






2-Ethoxy-




i-C


3


H


7










carbonl-C


6


H


4








2096




CH


3






2-Ethoxy-




n-C


4


H


9










carbonyl-C


6


H


4








2097




CH


3






2-Ethoxy-




t-C


4


H


9










carbonyl-C


6


H


4








2098




CH


3






2-Ethoxy-




n-C


6


H


13










carbonyl-C


6


H


4








2099




CH


3






2-Ethoxy-




Prop-1-en-3-yl








carbonyl-C


6


H


4








2100




CH


3






2-Ethoxy-




(E)-1-Chloroprop-1-en-3-yl








carbonyl-C


6


H


4








2101




CH


3






2-Ethoxy-




Propyn-3-yl








carbonyl-C


6


H


4








2102




CH


3






2-Ethoxy-




3-Methyl-but-2-en-1-yl








carbonyl-C


6


H


4








2103




CH


3






3-Ethoxy-




H








carbonyl-C


6


H


4








2104




CH


3






3-Ethoxy-




CH


3










carbonyl-C


6


H


4








2105




CH


3






3-Ethoxy-




C


2


H


5










carbonyl-C


6


H


4








2106




CH


3






3-Ethoxy-




n-C


3


H


7










carbonyl-C


6


H


4








2107




CH


3






3-Ethoxy-




i-C


3


H


7










carbonyl-C


6


H


4








2108




CH


3






3-Ethoxy-




n-C


4


H


9










carbonyl-C


6


H


4








2109




CH


3






3-Ethoxy-




t-C


4


H


9










carbonyl-C


6


H


4








2110




CH


3






3-Ethoxy-




n-C


6


H


13










carbonyl-C


6


H


4








2111




CH


3






3-Ethoxy-




Prop-1-en-3-yl








carbonyl-C


6


H


4








2112




CH


3






3-Ethoxy-




(E)-1-Chloroprop-1-en-3-yl








carbonyl-C


6


H


4








2113




CH


3






3-Ethoxy-




Propyn-3-yl








carbonyl-C


6


H


4








2114




CH


3






3-Ethoxy-




3-Methyl-but-2-en-1-yl








carbonyl-C


6


H


4








2115




CH


3






4-Ethoxy-




H








carbonyl-C


6


H


4








2116




CH


3






4-Ethoxy-




CH


3










carbonyl-C


6


H


4








2117




CH


3






4-Ethoxy-




C


2


H


5










carbonyl-C


6


H


4








2118




CH


3






4-Ethoxy-




n-C


3


H


7










carbonyl-C


6


H


4








2119




CH


3






4-Ethoxy-




i-C


3


H


7










carbonyl-C


6


H


4








2120




CH


3






4-Ethoxy-




n-C


4


H


9










carbonyl-C


6


H


4








2121




CH


3






4-Ethoxy-




t-C


4


H


9










carbonyl-C


6


H


4








2122




CH


3






4-Ethoxy-




n-C


6


H


13










carbonyl-C


6


H


4








2123




CH


3






4-Ethoxy-




Prop-1-en-3-yl








carbonyl-C


6


H


4








2124




CH


3






4-Ethoxy-




(E)-1-Chloroprop-1-en-3-yl








carbonyl-C


6


H


4








2125




CH


3






4-Ethoxy-




Propyn-3-yl








carbonyl-C


6


H


4








2126




CH


3






4-Ethoxy-




3-Methyl-but-2-en-1-yl








carbonyl-C


6


H


4








2127




CH


3






2-Amino-




H








carbonyl-C


6


H


4








2128




CH


3






2-Amino-




CH


3










carbonyl-C


6


H


4








2129




CH


3






2-Amino-




C


2


H


5










carbonyl-C


6


H


4








2130




CH


3






2-Amino-




n-C


3


H


7










carbonyl-C


6


H


4








2131




CH


3






2-Amino-




i-C


3


H


7










carbonyl-C


6


H


4








2132




CH


3






2-Amino-




n-C


4


H


9










carbonyl-C


6


H


4








2133




cH3




2-Amino-




t-C


4


H


9










carbonyl-C


6


H


4








2134




CH


3






2-Amino-




n-C


6


H


13










carbonyl-C


6


H


4








2135




CH


3






2-Amino-




Prop-1-en-3-yl








carbonyl-C


6


H


4








2136




CH


3






2-Amino-




(E)-1-Chloroprop-1-en-3-yl








carbonyl-C


6


H


4








2137




CH


3






2-Amino-




Propyn-3-yl








carbonyl-C


6


H


4








2138




CH


3






2-Amino-




3-Methyl-but-2-en-1-yl








carbonyl-C


6


H


4








2139




CH


3






3-Amino-




H








carbonyl-C


6


H


4








2140




CH


3






3-Amino-




CH


3










carbonyl-C


6


H


4








2141




CH


3






3-Amino-




C


2


H


5










carbonyl-C


6


H


4








2142




CH


3






3-Amino-




n-C


3


H


7










carbonyl-C


6


H


4








2143




CH


3






3-Amino-




i-C


3


H


7










carbonyl-C


6


H


4








2144




CH


3






3-Amino-




n-C


4


H


9










carbonyl-C


6


H


4








2145




CH


3






3-Amino-




t-C


4


H


9










carbonyl-C


6


H


4








2146




CH


3






3-Amino-




n-C


6


H


13










carbonyl-C


6


H


4








2147




CH


3






3-Amino-




Prop-1-en-3-yl








carbonyl-C


6


H


4








2148




CH


3






3-Amino-




(E)-1-Chloroprop-1-en-3-yl








carbonyl-C


6


H


4








2149




CH


3






3-Amino-




Propyn-3-yl








carbonyl-C


6


H


4








2150




CH


3






3-Amino-




3-Methyl-but-2-en-1-yl








carbonyl-C


6


H


4








2151




CH


3






4-Amino-




H








carbonyl-C


6


H


4








2152




CH


3






4-Amino-




CH


3










carbonyl-C


6


H


4








2153




CH


3






4-Amino-




C


2


H


5










carbonyl-C


6


H


4








2154




CH


3






4-Amino-




n-C


3


H


7










carbonyl-C


6


H


4








2155




CH


3






4-Amino-




i-C


3


H


7










carbonyl-C


6


H


4








2156




CH


3






4-Amino-




n-C


4


H


9










carbonyl-C


6


H


4








2157




CH


3






4-Amino-




t-C


4


H


9










carbonyl-C


6


H


4








2158




CH


3






4-Amino-




n-C


6


H


13










carbonyl-C


6


H


4








2159




CH


3






4-Amino-




Prop-1-en-3-yl








carbonyl-C


6


H


4








2160




CH


3






4-Amino-




(E)-1-Chloroprop-1-en-3-yl








carbonyl-C


6


H


4








2161




CH


3






4-Amino-




Propyn-3-yl








carbonyl-C


6


H


4








2162




CH


3






4-Amino-




3-Methyl-but-2-en-1-yl








carbonyl-C


6


H


4








2163




CH


3






2-(N-Methylamino-




H








carbonyl)-C


6


H


4








2164




CH


3






2-(N-Methylamino-




CH


3










carbonyl)-C


6


H


4








2165




CH


3






2-(N-Methylamino-




C


2


H


5










carbonyl)-C


6


H


4








2166




CH


3






2-(N-Methylamino-




n-C


3


H


7










carbonyl)-C


6


H


4








2167




CH


3






2-(N-Methylamino-




i-C


3


H


7










carbonyl)-C


6


H


4








2168




CH


3






2-(N-Methylamino-




n-C


4


H


9










carbonyl)-C


6


H


4








2169




CH


3






2-(N-Methylamino-




t-C


4


H


9










carbonyl)-C


6


H


4








2170




CH


3






2-(N-Methylamino-




n-C


6


H


13










carbonyl)-C


6


H


4








2171




CH


3






2-(N-Methylamino-




Prop-1-en-3-yl








carbonyl)-C


6


H


4








2172




CH


3






2-(N-Methylamino-




(E)-1-Chloroprop-1-en-3-yl








carbonyl)-C


6


H


4








2173




CH


3






2-(N-Methylamino-




Propyn-3-yl








carbonyl)-C


6


H


4








2174




CH


3






2-(N-Methylamino-




3-Methyl-but-2-en-1-yl








carbonyl)-C


6


H


4








2175




CH


3






3-(N-Methylanino-




H








carbonyl)-C


6


H


4








2176




CH


3






3-(N-Methylamino-




CH


3










carbonyl)-C


6


H


4








2177




CH


3






3-(N-Methylamino-




C


2


H


5










carbonyl)-C


6


H


4








2178




CH


3






3-(N-Methylamino-




n-C


3


H


7










carbonyl)-C


6


H


4








2179




CH


3






3-(N-Methylamino-




i-C


3


H


7










carbonyl)-C


6


H


4








2180




CH


3






3-(N-Methylamino-




n-C


4


H


9










carbonyl)-C


6


H


4








2181




CH


3






3-(N-Methylamino-




t-C


4


H


9










carbonyl)-C


6


H


4








2182




CH


3






3-(N-Methylamino-




n-C


6


H


13










carbonyl)-C


6


H


4








2183




CH


3






3-(N-Methylamino-




Prop-1-en-3-yl








carbonyl)-C


6


H


4








2184




CH


3






3-(N-Methylamino-




(E)-1-Chloroprop-1-en-3-yl








carbonyl)-C


6


H


4








2185




CH


3






3-(N-Methylamino-




Propyn-3-yl








carbonyl)-C


6


H


4








2186




CH


3






3-(N-Methylamino-




3-Methyl-but-2-en-1-yl








carbonyl)-C


6


H


4








2187




CH


3






4-(N-Methylamino-




H








carbonyl)-C


6


H


4








2188




CH


3






4-(N-Methylamino-




CH


3










carbonyl)-C


6


H


4








2189




CH


3






4-(N-Methylamino-




C


2


H


5










carbonyl)-C


6


H


4








2190




CH


3






4-(N-Methylamino-




n-C


3


H


7










carbonyl)-C


6


H


4








2191




CH


3






4-(N-Methylamino-




i-C


3


H


7










carbonyl)-C


6


H


4








2192




CH


3






4-(N-Methylamino-




n-C


4


H


9










carbonyl)-C


6


H


4








2193




CH


3






4-(N-Methylamino-




t-C


4


H


9










carbonyl)-C


6


H


4








2194




CH


3






4-(N-Methylamino-




n-C


6


H


13










carbonyl)-C


6


H


4








2195




CH


3






4-(N-Methylamino-




Prop-1-en-3-yl








carbonyl)-C


6


H


4








2196




CH


3






4-(N-Methylamino-




(E)-1-Chloroprop-1-en-3-yl








carbonyl)-C


6


H


4








2197




CH


3






4-(N-Methylamino-




Propyn-3-yl








carbonyl)-C


6


H


4








2198




CH


3






4-(N-Methylamino-




3-Methyl-but-2-en-1-yl








carbonyl)-C


6


H


4








2199




CH


3






2-Dimethylamino-




H








carbonyl-C


6


H


4








2200




CH


3






2-Dimethylamino-




CH


3










carbonyl-C


6


H


4








2201




CH


3






2-Dimethylamino-




C


2


H


5










carbonyl-C


6


H


4








2202




CH


3






2-Dimethylamino-




n-C


3


H


7










carbonyl-C


6


H


4








2203




CH


3






2-Dimethylamino-




i-C


3


H


7










carbonyl-C


6


H


4


—






2204




CH


3






2-Dimethylamino-




n-C


4


H


9










carbonyl-C


6


H


4








2205




CH


3






2-Dimethylamino-




t-C


4


H


9










carbonyl-C


6


H


4








2206




CH


3






2-Dimethylamino-




n-C


6


H


13










carbonyl-C


6


H


4








2207




CH


3






2-Dimethylamino-




Prop-1-en-3-yl








carbonyl-C


6


H


4








2208




CH


3






2-Dimethylamino-




(E)-1-Chloroprop-1-en-3-yl








carbonyl-C


6


H


4








2209




CH


3






2-Dimethylamino-




Propyn-3-yl








carbonyl-C


6


H


4








2210




CH


3






2-Dimethylamino-




3-Methyl-but-2-en-1-yl








carbonyl-C


6


H


4








2211




CH


3






3-Dimethylamino-




H








carbonyl-C


6


H


4








2212




CH


3






3-Dimethylamino-




CH


3










carbonyl-C


6


H


4








2213




CH


3






3-Dimethylamino-




C


2


H


5










carbonyl-C


6


H


4








2214




CH


3






3-Dimethylamino-




n-C


3


H


7










carbonyl-C


6


H


4








2215




CH


3






3-Dimethylamino-




i-C


3


H


7










carbonyl-C


6


H


4








2216




CH


3






3-Dimethylamino-




n-C


4


H


9










carbonyl-C


6


H


4








2217




CH


3






3-Dimethylamino-




t-C


4


H


9










carbonyl-C


6


H


4








2218




CH


3






3-Dimethylamino-




n-C


6


H


13










carbonyl-C


6


H


4








2219




CH


3






3-Dimethylamino-




Prop-1-en-3-yl








carbonyl-C


6


H


4








2220




CH


3






3-Dimethylamino-




(E)-1-Chloroprop-1-en-3-yl








carbonyl-C


6


H


4








2221




CH


3






3-Dimethylamino-




Propyn-3-yl








carbonyl-C


6


H


4








2222




CH


3






3-Dimethylamino-




3-Methyl-but-2-en-1-yl








carbonyl-C


6


H


4








2223




CH


3






4-Dimethylamino-




H








carbonyl-C


6


H


4








2224




CH


3






4-Dimethylamino-




CH


3










carbonyl-C


6


H


4








2225




CH


3






4-Dimethylamino-




C


2


H


5










carbonyl-C


6


H


4








2226




CH


3






4-Dimethylamino-




n-C


3


H


7










carbonyl-C


6


H


4








2227




CH


3






4-Dimethylamino-




i-C


3


H


7










carbonyl-C


6


H


4








2228




CH


3






4-Dimethylamino-




n-C


4


H


9










carbonyl-C


6


H


4








2229




CH


3






4-Dimethylamino-




t-C


4


H


9










carbonyl-C


6


H


4








2230




CH


3






4-Dimethylamino-




n-C


6


H


13










carbonyl-C


6


H


4








2231




CH


3






4-Dimethylamino-




Prop-1-en-3-yl








carbonyl-C


6


H


4








2232




CH


3






4-Dimethylamino-




(E)-1-Chloroprop-1-en-3-yl








carbonyl-C


6


H


4








2233




CH


3






4-Dimethylamino-




Propyn-3-yl








carbonyl-C


6


H


4








2234




CH


3






4-Dimethylamino-




3-Methyl-but-2-en-1-yl








carbonyl-C


6


H


4
















The compounds I are suitable as fungicides.




The compounds I are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes and Basidiomycetes. They are systemically active in some cases and can be employed as foliar and soil fungicides.




They are of particular importance for the control of a multiplicity of fungi on various crop plants such as wheat, rye, barley, oats, rice, corn, grass, cotton, soybean, coffee, sugar cane, grapes, fruit and decorative plants and vegetable plants such as cucumbers, beans and cucurbits, and on the seeds of these plants.




They are specifically suitable for the control of the following plant diseases:


Erysiphe graminis


(powdery mildew) in cereals,


Erysiphe cichoracearum


and


Sphaerotheca fuliginea


on cucurb its,


Podosphaera leucotricha


on apples,


Uncinula necator


on vines, Puccinia species on cereals, Rhizoctonia species on cotton and lawns, Ustilago species on cereals and sugar cane,


Venturia inaequalis


(scab) on apples, Helminthosporium species on cereals,


Septoria nodorum


on wheat,


Botrytis cinerea


(gray mold) on strawberries, vines,


Cercospora arachidicola


on groundnuts,


Pseudocercosporella herpotrichoides


on wheat, barley,


Pyricularia oryzae


on rice,


Phytophthora infestans


on potatoes and tomatoes, Fusarium and Verticillium species on various plants,


Plasmopara viticola


on vines, Alternaria species on vegetables and fruit.




The compounds I are applied by treating the fungi or the plants, seeds, materials or the soil to be protected from fungal attack with a fungicidally effective amount of the active compounds. They are applied before or after the infection of the materials, plants or seeds by the fungi.




They can be converted into the customary formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application form depends on the particular intended use; it should in any case guarantee a fine and uniform dispersion of the ortho-substituted benzyl ester of a cyclopropanecarbonic acid. The formulations are prepared in a known manner, eg. by extending the active compound with solvents and/or carriers, if desired using emulsifiers and dispersants, it also being possible to use other organic solvents as auxiliary solvents when water is used as a diluent. Suitable auxiliary substances for this purpose are essentially: solvents such as aromatics (eg. xylene), chlorinated aromatics (eg. chlorobenzenes), paraffins (eg. petroleum fractions), alcohols (eg. methanol, butanol), ketones (eg. cyclohexanone), amines (eg. ethanolamine, dimethylformamide) and water; carriers such as ground natural minerals (eg. kaolins, clays, talc, chalk) and ground synthetic minerals (eg. highly disperse silicic acid, silicates); emulsifiers such as nonionic and anionic emulsifiers (eg. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin-sulfite waste liquors and methylcellulose.




The fungicidal compositions in general contain from 0.1 to 95, preferably from 0.5 to 90, % by weight of active compound.




Depending on the type of effect desired, the application rates are from 0.01 to 2.0 kg of active compound per ha.




In seed treatment, active compound amounts of from 0.001 to 0.1 g, preferably from 0.01 to 0.05 g, per kilogram of seed are in general needed.




The compositions according to the invention can also be present in the application form as fungicides together with other active compounds, the eg. with herbicides, insecticides, growth regulators, fungicides or alternatively with fertilizers.




On mixing with fungicides, in many cases an increase in the fungicidal spectrum of action is obtained here.




The following list of fungicides with which the compounds according to the invention can be applied together is intended to illustrate the combination possibilities, but not restrict them:




sulfur, dithiocarbamates and their derivatives, such as ferric dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediamine bisdithiocarbamate, tetramethylthiuram disulfides, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate), ammonia complex of zinc (N,N′-propylenebisdithiocarbamate), zinc (N,N′-propylenebisdithiocarbamate), N,N′-polypropylenebis(thiocarbamoyl) disulfide;




nitro derivatives, such as dinitro(1-methylheptyl)phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl isopropylcarbonate, diisopropyl 5-nitroisophthalate;




heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethyl phthalimidophosphonothioate, 5-amino-1-[bis(dimethylamino)phosphinyl]-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithiolo[4,5-b]quinoxaline, methyl 1-(butylcarbamoyl)-2-benzimidazole carbamate, 2-methoxycarbonylaminobenzimidazole, 2-(fur-2-yl)benzimidazole, 2-(thiazol-4-yl)benzimidazole, N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide;




N-dichlorofluoromethylthio-N′,N′-dimethyl-N-phenylsulfamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, pyridine-2-mercapto-1-oxide, 3-hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide, 2,4,5-trimethylfuran-3-carboxanilide, N-cyclohexyl-2,5-dimethylfuran-3-carboxamide, N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine-2,2,2-trichloroethyl acetal, piperazine-1,4-diyl-bis(1-(2,2,2-trichloroethyl))formamide, 1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclododecylmorpholine or its salts, N-[3-(p-tert-butylphenyl)-2-methylpropyl)-cis-2,6-dimethylmorpholine, N-[3-(p-tert-butylphenyl)-2-methylpropyl]piperidine, 1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-yl-ethyl]-1H-1,2,4-triazole, 1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole, N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N′-imidazolylurea, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol, α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol, 5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene, 1,2-bis(3-methoxycarbonyl-2-thio-ureido)benzene,




and also various fungicides, such as dodecylguanidine acetate, 3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]glutarimide, hexachlorobenzene, DL-methyl-N-(2,6-dimethylphenyl)-N-2-furoyl alaninate, DL-N-(2,6-dimethylphenyl)-N-(2′-methoxyacetyl)alanine methyl ester, N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-aminobutyrolactone, DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)alanine methyl ester, 5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine, 3-[3,5-dichlorophenyl-(5-methyl-5-methoxymethyl]-1,3-oxazolidine-2,4-dione 3-(3,5-dichloropheyl)-1-isopropylcarbamoylhydantoin, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano-[N-(ethylamiocarbonyl)-2-methoximino]acetamide, 1-[2-(2,4-dichloropheyl)pentyl]-1H-1,2,4-triazole, 2,4-difluoro-α-(1H-1,2,4-triazoyl-1-methyl)benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine, 1-((bis(4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole.




The compounds of the formula I are additionally suitable for controlling pests from the class of insects, arachnids and nematodes effectively. They can be employed as pesticides in plant protection and in the hygiene, stored products protection and veterinary sectors.




The harmful insects include from the order of the butterflies (Lepidoptera), for example,


Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia 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 flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni, Zeiraphera canadensis.






From the order of the beetles (Coleoptera), for example,


Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica


12-


punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala,


Phyllophaga sp.,


Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus, Sitophilus granaria.






From the order of the dipterous insects (Diptera), for example,


Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina


[sic],


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, Tipula paludosa.






From the order of the thrips (Thysanoptera), for example,


Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci.






From the order of the hymenopterous insects (Hymenoptera), for example,


Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta.






From the order of the bed bugs (Heteroptera), for example,


Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor.






From the order of the plant-sucking insects (Homoptera), for example,


Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vaporariorum, Viteus vitifolii.






From the order of the termites (Isoptera), for example,


Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus, Termes natalensis.






From the order of the orthopterous insects (Orthoptera), for example,


Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus. maroccanus, Tachycines asynamorus.






From the class of the Arachnoidea, for example spiders (Acarina) such as


Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius, Tetranychus urticae.






From the class of the nematodes, for example, root gall nematodes, eg.


Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica,


cyst-forming nematodes, eg.


Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifoiji,


stem and leaf eelworms, eg.


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, Pratylenchus goodeyi.






The active compounds can be applied as such or in the form of their formulations or the application forms prepared therefrom, eg. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering compositions or granules by spraying, atomizing, dusting, scattering or pouring. The application forms depend entirely on the purposes of use; they should in any case as far as possible guarantee the finest dispersion of the active compounds according to the invention.




The active compound concentrations in the ready-for-application preparations can be varied within quite substantial ranges.




In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%.




The active compounds can also be used with great success in ultra-low volume processes (ULV), where it is possible to apply formulations containing more than 95% by weight of active compound or even the active compound without additives.




The application rate of active compound for controlling pests under outdoor conditions is from 0.1 to 2.0, preferably from 0.2 to 1.0 kg/ha.




For the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, and also coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, eg. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water are suitable.




Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (oil dispersions) by addition of water. For the preparation of emulsions, pastes or oil dispersions, the substances can be homogenized in water as such or dissolved in an oil or solvent, by means of wetting agents, tackifiers, dispersants or emulsifiers. However, concentrates consisting of active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil can also be prepared, which are suitable for dilution with water.




Suitable surface-active substances are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkylsulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali metal and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ether, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methylcellulose.




Powders, scattering compositions and dusts can be prepared by mixing or joint grinding of the active substances with a solid carrier.




The formulations in general contain from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compound. The active compounds are employed here in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).




Examples of formulations are:




I. 5 parts by weight of a compound according to the invention are intimately mixed with 95 parts by weight of finely divided kaolin. A dust which contains 5% by weight of the active compound is obtained in this way.




II. 30 parts by weight of a compound according to the invention are intimately mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed on the surface of this silica gel. A preparation of the active compound having good adhesion is obtained in this way (active compound content 23% by weight).




III. 10 parts by weight of a compound according to the invention are dissolved in a mixture which consists of 90 parts by weight of xylene, 6 parts by weight of the addition product of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 2 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil (active compound content 9% by weight).




IV. 20 parts by weight of a compound according to the invention are dissolved in a mixture which consists of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the addition product of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 5 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil (active compound content 16% by weight).




V. 80 parts by weight of a compound according to the invention are well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel and the mixture is ground in a hammer mill (active compound content 80% by weight).




VI. 90 parts by weight of a compound according to the invention are mixed with 10 parts by weight of N-methyl-α-pyrrolidone and a solution is obtained which is suitable for application in the form of very small drops (active compound content 90% by weight).




VII. 20 parts by weight of a compound No. 11 according to the invention are dissolved in a mixture which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition product of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil. By pouring the solution into and finely dispersing it in 100,000 parts by weight of water, an aqueous dispersion is obtained which contains 0.02% by weight of the active compound.




VIII. 20 parts by weight of a compound according to the invention are well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and the mixture is ground in a hammer mill. By finely dispersing the mixture in 20,000 parts by weight of water, a spray liquor is obtained which contains 0.1% by weight of the active compound.




Granules, eg. coated, impregnated and homogeneous granules, can be produced by binding the active compounds to solid carriers. Solid carriers are eg. mineral earths, such as silica gel, asilicic acids, silica gels silicates, talc, kaolin, attapulgite, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as eg. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as grain meal, tree bark, wood and nut shell meal, cellulose powder and other solid carriers.




Oils of various types, herbicides, fungicides, other pesticides and bactericides can be added to the active compounds, if appropriate even only immediately before application (tank mix). These agents can be admixed to the compositions according to the invention in the weight ratio 1:10-10:1.











SYNTHESIS EXAMPLES




The procedures presented in the synthesis examples below were utilized with appropriate modification of the starting compounds to obtain further compounds I. The compounds thus obtained are shown in the following tables with physical data.




Example 1




Preparation of methyl (E,E)-2-methoxyimino-2-[2′-(1″-methyl, 1″-acetyl)iminooxymethyl]phenylacetate




21 g (0.21 mol) of diacetyl monoxime are added under protective gas and with slight cooling at room temperature to 6.4 g (0.21 mol) of sodium hydride (80%) in 150 ml of dry dimethylformamide and the mixture is stirred for 30 min at room temperature. A solution of 60 g (0.21 mol) of methyl 2-methoxyimino-2-(2′bromomethyl)phenylacetate in 360 ml of dimethylformamide is then added dropwise and the mixture is stirred at room temperature for 16 h. After addition of 10% strength hydrochloric acid, it is extracted with methyl tert-butyl ether. The combined organic phases are washed with water, dried over Na


2


SO


4


and concentrated. The residue is suspended in a little cold methanol. After filtering off with suction, 38 g (59%) of the title compound are obtained as light brown crystals having a melting point of 69-71° C.






1


H-NMR (CDCl


3


):δ=1.87(s,3H); 2.30(s,3H); 3.85(s,3H); 4.05(s,3H); 5.15(s,2H); 7.17-7.48(m,4H) ppm.




Example 2




Preparation of methyl (E,E,E)-2-methoxyimino-2-[2′-(1″-methyl, 1″-(1″′-ethoxyiminoethyl))iminooxymethyl]phenylacetate




0.96 g (9.8 mmol) of O-ethylhydroxylamine hydrochloride and 0.6 g of dry molecular sieve beads (3 A) are added to a solution of 2.5 g (8.2 mmol) of methyl (E,E)-2-methoxyimino-2-[2′-(1″-methyl, 1″-acetyl)iminooxymethyl]phenylacetate in 60 ml of warm methanol after cooling to room temperature and the mixture is allowed to stand at room temperature for 5 days. After filtering off the molecular sieve, the solution is concentrated, the residue is partitioned between methyl tert-butyl ether and water, and the organic phase is washed with water, dried over Na


2


SO


4


and concentrated. After triturating the residue with n-hexane and filtering off with suction, 1.8 g (63%) of the title compound are obtained as pale yellow crystals having a melting point of 69-72° C.






1


H-NMR (CDCl


3


):δ=1.27(t,3H); 1.96(s,3H); 1.99(s,3H); 3.84(s,3H); 4.04(s,3H); 4.17(q,2H); 5.06(s,2H); 7.17-7.49(m,4H) ppm




Example 3




Preparation of (E,E,E)-2-methoxyimino-2-[2′-(1″-methyl, 1″-(1″′-ethoxyiminoethyl))iminooxymethyl]phenylacetic acid monomethylamide




0.90 g (2.60 mmol) of methyl (E,E,E)-2-methoxyimino-2-[2′-(1″-methyl,1″-(1″′-ethoxyiminoethyl))iminooxymethyl]-phenylacetate is dissolved in 50 ml of tetrahydrofuran, treated with 2.0 g of 40% strength aqueous monomethylamine solution and stirred et room temperature for 16 h. The mixture is then treated with water and extracted with methyl tert-butyl ether, and the organic phase is washed with water, dried over Na


2


SO


4


and concentrated on a rotary evaporator. As a residue, 0.80 g (89%) of the title compound remains as a pale yellow oil.






1


H-NMR (CDCl


3


):δ=1.28(t,3H); 1.97(s,3H); 1.99(s,3H); 2.90(d,3H); 3.96(s,3H); 4.18(q,2H); 5.07(s,2H); 6.74(br,1H);7.17-7.48(m,4H) ppm.




Example 4




Preparation of 4-hydroxyimino-2,2-dimethylpentan-3-one




A solution of 40 g of hydrogen chloride in 156 g of diethyl ether is added dropwise at room temperature to 96 g (0.84 mol) of 2,2-dimethyl-3-pentanone in 960 g of toluene. After cooling to −10° C., a solution of 95 g of n-butyl nitrite in 470 g of diethyl ether is added dropwise. The mixture is stirred at from −10° C. to 0° C. for 4 hours and then allowed to come to room temperature. After a total of 16 h, the reaction mixture is washed three times with 1 l of ice-water each time and then extracted twice with 1 l of 1M sodium hydroxide solution each time. The alkaline phase is separated off and neutralized with 20% strength sulfuric acid. The crude product is filtered off with suction and, after drying, recrystallized from n-hexane. 66 g (55%) of the title compound are obtained as a pale yellow powder of melting point 107-110° C.






1


H-NMR (CDCl


3


):δ=1.29(s,9H); 1.99(s,3H); 8.30(s,1H) ppm.




Example 5




Preparation of methyl (E)-2-methoxyimino-2-[2′-(1″-methyl, 1″-(1″′,1″′-dimethylethylcarbonyl))iminooxymethyl]phenylacetate




25 g (0.17 mol) of 4-hydroxyimino-2,2-dimethylpentan-3-one are added in portions under protective gas to 6.4 g (0.21 mol) of sodium hydride (80%) in 150 ml of dry dimethylformamide, the reaction mixture warming to 50° C. stirring is continued for 30 min, then a solution of 50 g (0.17 mol) of methyl 2-methoxyimino-2-(2′-bromomethyl)phenylacetate in 300 ml of dimethylformamide is added dropwise and the mixture is stirred at room temperature for 16 h. After addition of 10% strength hydrochloric acid, it is extracted with methyl tert-butyl ether. The combined organic phases are washed with water, dried over Na


2


SO


2


[sic] and concentrated. The black oily residue is purified by column chromatography on silica gel (methyl tert-butyl ether/n-hexane) and the tube crude product thus obtained is suspended in ice-cold methanol. After filtering off with suction, 24 g (41%) of the title compound are obtained as an almost colorless powder of melting point 58-62° C.






1


H-NMR (CDCl


3


):δ=1.19(s,9H); 1.90(s,3H); 3.83(s,3H); 4.04(s,3H); 5.11(s,2H); 7.18-7.45(m,4H) ppm.




Example 6




Preparation of methyl (E)-2-methoxyimino-2-[2′-(1″-methyl, 1″-(1″′-(6″″-(4″″′-chlorophenyl)hexyloxyimino), 2″′, 2″′-dimethylpropyl))iminooxymethyl]phenylacetate




5.9 g (26 mmol) of O-6-(4′-chlorophenyl)hexylhydroxylamine, 3.6 g of dry molecular sieve beads (3 A) and 1.6 g (8.6 mmol) of p-toluenesulfonic acid hydrate are added to a solution of 3.0 g (8.6 mmol) of methyl (E)-2-methoxyimino-2-[2′-(1″- methyl, 1″-(1″′, 1″′-dimethylethylcarbonyl))iminooxymethyl]phenylacetate in 60 ml of warm methanol after cooling to room temperature and the mixture is refluxed for 3 h. After filtering off the molecular sieve, the solution is concentrated, the residue is partitioned between methyl tert-butyl ether and water, and the organic phase is washed with water, dried over Na


2


SO


4


and concentrated. After column chromatography on silica gel (hexane/methyl tert-butyl ether), 3.8 g (79%) of the title compound are obtained as a pale yellow oil.






1


H-NMR (CDCl


3


):δ=1.09(s,9H); 1.26-1.42(m,4H); 1.52-1.67(m,4H); 1.90(s,3H); 2.57(t,2H); 3.84(s,3H); 3.99(t,2H); 4.03(s,3H); 5.02(s,2H); 7.07-7.47(m,8H) ppm.




Example 7




Preparation of (E)-2-methoxyimino-2-[2′-(1″-methyl, 1″-(1″′-(6″″-(4″″′-chlorophenyl)hexyloxyimino), 2″′, 2″′-dimethylpropyl))iminooxymethyl]phenylacetic acid monomethylamide




2.8 g (5.0 mmol) of methyl (E)-2-methoxyimino-2-[2′-(1″-methyl, 1″-(1″′-(6″″-(4″″′-chlorophenyl)hexyloxyimino), 2″′, 2″′-dimethylpropyl)iminooxymethyl]phenylacetate are dissolved in 10 ml of tetrahydrofuran, treated with 3.9 g of 40% strength aqueous monomethylamine solution and stirred at room temperature for 16 h. The mixture is then treated with water and extracted with methyl tert-butyl ether, and the organic phase is washed with water, dried over Na


2


SO


4


and concentrated on a rotary evaporator. As a residue, 2.3 g (82%) of the title compound remain as a colorless oil.






1


H-NMR (CDCl


3


):δ=1.08(s,9H); 1.26-1.41(m,4H); 1.53-1.67(m,4H); 1.89(s,3H); 2.56(t,2H); 2.87(d,3H); 3.93(s,3H); 3.99(t,2H); 5.02(s,2H); 6.74(s,broad,1H); 7.05-7.45(m,8H) ppm.




Example 8




Preparation of (E)-2-methoxyimino-2-[2′-(1″-methyl, 1″(1″′-methoxyimino, 1″′paramethoxyphenyl)methyl)iminooxymethyl]phenylacetic acid monomethylthioamide (Cpd. II.01, Table II)




1.9 g (4.5 mmol) of (E)-2-methoxyimino-2-[2′-(1″-methyl, 1″(1″′-methoxyimino, 1″′paramethoxyphenyl)methyl)iminooxy-methyl]phenylacetic acid monomethylamide are dissolved in 80 ml of xylene, treated with 1.8 g (4.5 mmol) of Lawesson's reagent and stirred at 100° C. for 45 min.




The reaction solution is concentrated and the residue is purified by column chromatography.




1.5 g (75%) of the title compound are isolated as an isomer mixture in the form of a yellowish oil.




IR [cm


−1


] Film: 834, 977, 1027, 1065, 1175, 1251, 1358, 1512, 1608, 2936, 3330




Example 9




Isomerization of (E)-2-methoxyimono-2-[2′-(1″-methyl, 1″-(1″′-(Z/E)methoxyimino [sic], 1″′-phenyl)methyl)-(E)-iminooxymethyl]phenylacetic acid monomethylamide to (E)-2-methoxyimino-2-[2′-(1″-methyl, 1″-(1″′-(E)-methoxyimino [sic], 1″′-phenyl)methyl]-(E)-iminooxymethyl]phenylacetic acid monomethylamide:




5 g of E,E,E/E,Z,E isomer mixture (30:70) are dissolved in 50 ml of methanol, treated with 15 ml of methanol saturated with HCl and allowed to stand at room temperature for 18 hours. The reaction solution is added to ice-water and extracted with dichloromethane, and the extract is dried over Na


2


SO


4


. After concentrating on the rotary evaporator, 5 g of an oil (E,E,E:E,Z,E, approx. 65:35) are obtained. The desired (E,E,E)-isomer crystallizes on addition of methanol (2.1 g=42%) in the form of a colorless solid. M.p. (E,E,E-isomer): 134-136° C.




Note: The filtrate can be isomerized again using methanol HCl.












TABLE I










































No.




R


2




m






R


3






R


4






R


5






Data









I.01




H




CH


3






CH


3






H




m.p.: 135-138° C.






I.02




H




CH


3






CH


3






CH


3






m.p.: 78-82° C.






I.03




H




CH


3






CH


3






C


2


H


5






oil; IR (Film): 3350,











2975, 2937, 1669,











1526, 1366, 1092,











1039, 980, 920, 890






I.04




H




CH


3






CH


3






i-C


3


H


7






oil;


1


H-NMR(CDCl


3


)I: δ =











1.26(d, 6H);











1.95(s, 3H);











2.0(s, 3H)











2.91(d, 3H);











3.96(s, 3H);











4.37(q, 1H);











5.06(s, 2H),











6.72(s, br, 1H);











7.17-7.50(m, 4H) ppm






I.05




H




CH


3






CH


3






n-C


4


H


9






m.p.: 89-93° C.






I.06




H




CH


3






CH


3






t-C


4


H


9






oil;


1


H-NMR(CDCl


3


): δ =











1.29(s, 9H);











1.94(s, 3H);











2.00(s, 3H);











2.90(d, 3H);











3.96(s, 3H);











5.06(s, 2H);











6.70(s, br, 1H);











7.17-747(m, 4H) ppm






I.07




H




CH


3






CH


3






n-C


6


H


13






m.p.: 83-85° C.






I.08




H




CH


3






CH


3






CH


2


CN




m.p.: 92-96° C.






I.09




H




CH


3






CH


3






CH


2


CH


2


CN




m.p.: 92-96° C.






I.10




H




CH


3






CH


3






3-Methyl-




m.p.: 86-88° C.










but-2-en-1-yl






I.11




H




CH


3






CH


3






4-Cl—C


6


H


4


—CH


2






m.p.: 152-154° C.






I.12




H




CH


3






CH


3






2-Naphthyl-CH


2






oil;


1


H-NMR(CDCl


3


): δ =











1.98(s, 3H);











2.02(s, 3H)











2.87(d, 3H);











3.92(s, 3H);











5.06(s, 2H);











5.33(s, 2H);











6.70(s, br, 1H);











7.17-7.88(m, 11H) ppm






I.13




H




CH


3






CH


3






6-(4′-Chloro-




oil;


1


H-NMR(CDCl


3


): δ =










phenyl)hex-1-yl




1.27-1.70(m, 8H);











1.95(s, 3H);











1.98(s, 3H);











2.58(t-2H);











2.90(d, 3H);











3.95(s, 3H);











4.10(t, 2H);











5.06(s, 2H);











6.71(s, br, 1H);











7.08-7.46(m, 8H) ppm






I.14




H




CH


3






CH


3






3-CF


3


—C


6


H


4






m.p.: 119-124° C.






I.15




H




CH


3






CH


3






4-CF


3


, 6-Cl-




m.p.: 129-132° C.










pyrid-2-yl






I.16




H




CH


3






CH


3






4-CF


3


-pyrid-2-yl




m.p.: 144-147° C.






I.17




H




CH


3






CH


3






(E)-1-Chloropropen-




m.p.: 96-98° C.










3-yl






I.18




H




CH


3






CH


3






(E)-4-(4′-




oil;


1


H-NMR(CDCl


3


):










Chlorophenyl)-




1.97(s, 6H);










but-2-en-1-yl




2.90(d, 3H);











3.36(d, 2H);











3.96(s, 3H);











4.60(d, 2H);











5.06(s, 2H);











5.65-5.92(m, 2H);











7.68(s, br, 1H);











7.09-7.48(m, 8H) ppm






I.19




H




CH


3






CH


3






Propyn-3-yl




m.p.: 106-109° C.






I.20




H




CH


3






CH


3






2-Hydroxy-




JR: 884, 929, 980,










prop-1-yl




1036, 1092, 1366,











1529, 1665, 2937,











3370






I.21




H




CH


3






CH


3






6-Hydroxy-2-




217-220° C.










methyl-pyrimidin-










4-ylmethyl






I.22




H




CH


3






CH


3






6-Hydroxy-2-iso-




219-221° C.










propyl-pyrimidin-










4-ylmethyl






I.23




H




CH


3






CH


3






6-Hydroxy-2-




220-224° C.










cyclopropyl-










pyrimidin-4-ylmethyl






I.24




H




CH


3






CH


3






5-(2′-Furan)-




57-61° C.










pent-1-yl






I.25




H




CH


3






CH


3






5-(2′-N-Methyl-




40-44° C.










pyrrol)-pent-1-yl






I.26




H




CH


3






CH


3






2-(4′-Chloro-




110-120° C.










phenyl)-oxazol-










4-ylmethyl






I.27




H




CH


3






CH


3






3-Trifluoro-




104-107° C.










methylpyrid-2-yl






I.28




H




CH


3






CH


3






5-Trifluoro-




126-130° C.










methylpyrid-2-yl






I.29




H




CH


3






CH


3






6-(2′-Thiophen)-




694, 893, 980, 1037,










hex-1-yl




1092, 1365, 1525,











1673, 2935, 3340,











3400






I.30




H




CH


3






t-C


4


H


9






H




oil;


1


H-NMR(CDCl


3


): δ =











1.10(s, 9H);











1.95(s, 3H);











2.88(d, 3H);











3.95(s, 3H);











5.05(s, 2H);











6.76(s, br, 1H);











7.17-7.47(m, 4H);











8.04(s, 1H) ppm






I.31




H




CH


3






t-C


4


H


9






CH


3






oil; IR (Film):











3360, 2963, 2936,











1671, 1525, 1364,











1091, 1041, 979, 887






I.32




H




CH


3






t-C


4


H


9






C


2


H


5






oil; IR (Film):











3350, 2969, 2935,











1669, 1524, 1364,











1093, 1041, 978, 917,











883






I.33




H




CH


3






t-C


4


H


9






i-C


3


H


7






m.p.: 95-99° C.






I.34




H




CH


3






t-C


4


H


9






n-C


4


H


9






oil; IR (Film):











3360, 2958, 2935,











2872, 1671, 1525,











1364, 1092, 1037,











979, 922






I.35




H




CH


3






t-C


4


H


9






t-C


4


H


9






m.p.: 89-92° C.






I.36




H




CH


3






t-C


4


H


9






n-C


6


H


13






oil; IR (Film):











3360, 2956, 2933,











2870, 1675, 1525,











1364, 1093, 1039,











979, 918






I.37




H




CH


3






t-C


4


H


9






(E)-1-Chloro-




oil; IR (Film):










propen-3-yl




3360, 2966, 2935,











1673, 1526, 1365,











1093, 1037, 980, 918,











881






I.38




H




CH


3






t-C


4


H


9






Propyn-3-yl




oil; IR (Film):











3300, 2967, 2935,











1672, 1525, 1365,











1094, 1037, 1005,











979, 918






I.39




H




CH


3






t-C


4


H


9






3-Methyl-




oil; IR (Film):










but-2-en-1-yl




3360, 2968, 2935,











1675, 1525, 1364,











1093, 1038, 979, 919,











880






I.40




H




CH


3






t-C


4


H


9






2-Naphthyl-CH


2






oil; IR (Film):











3360, 2966, 2935,











1675, 1523, 1364,











1037, 1002, 979, 920,











752






I.41




H




CH


3






t-C


4


H


9






4-Cl—C


6


H


4


—CH


2






oil; IR (Film):











3360, 2970, 2945,











1677, 1525, 1492,











1365, 1090, 1038,











1014, 980, 919, 881






I.42




H




CH


3






t-C


4


H


9






(E)-4-(4′-




oil; IR (Film):










Chlorophenyl)-




3360, 2967, 1676,










but-2-en-1-yl




1525, 1491, 1365,











1093, 1037, 1015,











979, 919






I.43




H




CH


3






t-C


4


H


9






6-(4′-Chloro-




oil; IR (Film):










phenyl)hex-1-yl




3360, 2934, 1679,











1524, 1492, 1364,











1092, 1038, 1015, 979






I.44




H




CH


3






t-C


4


H


9






3-CF


3


—C


6


H


4






oil; IR (Film):











3360, 2975, 1675,











1450, 1331, 1168,











1126, 1092, 1038,











980, 940, 926






I.45




H




CH


3






C


6


H


5






H




m.p.: 165-167° C.






I.46




H




CH


3






C


6


H


5






CH


3






m.p.: 134-136° C.






I.47




H




CH


3






C


6


H


5






C


2


H


5






oil; IR (Film):











3340, 2938, 1674,











1526, 1445, 1091,











1037, 979, 925, 767,











694






I.48




H




CH


3






C


6


H


5






i-C


3


H


7






m.p.: 77-80° C.






I.49




H




CH


3






C


6


H


5






n-C


4


H


9






oil; IR (Film):











3340, 2958, 2936,











1675, 1525, 1445,











1092, 1070, 1036,











979, 694






I.50




H




CH


3






C


6


H


5






4-Cl—C


6


H


4


—CH


2






oil; IR (Film):











3340, 2937, 1675,











1522, 1492, 1445,











1091, 1036, 1012,











979, 918






I.51




H




CH


3






C


6


H


5






3-CF


3


—C


6


H


4






oil; IR (Film):











3340, 2930, 1675,











1449, 1328, 1169,











1126, 1062, 1038,











979, 944, 697






I.52




H




CH


3






C


6


H


5






6-(4′-Chloro-




oil; IR (Film):










phenyl)hex-1-yl




3340, 2935, 2858,











1679, 1524, 1492,











1445, 1091, 1037,











1015, 979






I.53




H




CH


3






C


6


H


5






(E)-4-(4′-




oil; IR (Film):










Chlorophenyl)-




3340, 2937, 1675,










but-2-en-1-yl




1525, 1491, 1444,











1092, 1036, 1015,











978, 918






I.54




H




C


6


H


5






C


6


H


5






CH


3






m.p.: 60-65° C.






I.55




H




C


6


H


5






C


6


H


5






C


2


H


5






m.p.: 45-48° C.






I.56




H




C


6


H


5






C


6


H


5






n-C


3


H


7






oil, IR [cm


−1


] (Film)











693, 766, 980, 1037,











1064, 1445, 1526,











1676, 2937, 2965,











3330, 3410






I.57




H




C


6


H


5






C


6


H


5






i-C


3


H


7






m.p. 53-58° C.






I.58




H




C


6


H


5






C


6


H


5






n-C


4


H


9






oil, IR [cm


−1


] (Film)











693, 766, 978, 1015,











1036, 1445, 1525,











1677, 2936, 2958,











3340, 3420






I.59




H




C


6


H


5






C


6


H


5






t-C


4


H


9






m.p.: 45-50° C.






I.60




H




C


6


H


5






C


6


H


5






n-C


6


H


13






oil, IR [cm


−1


] (Film)











693, 766, 979, 1014,











1037, 1445, 1525,











1678, 2934, 2954,











3330, 3410






I.61




H




C


6


H


5






C


6


H


5






3-Methyl-




oil, IR [cm


−1


] (Film)










but-2-en-1-yl




693, 766, 921, 979,











1037, 1445, 1493,











1526, 1675, 2937,











3330, 3410






I.62




H




CH


3






CH


3






4-Phenyl-




oil, IR [cm


−1


] (Film)










but-1-yl




700, 748, 894, 923,











979, 1037, 1365,











1524, 1673, 2938,











3340, 3410






I.63




H




CH


3






CH


3






4-Phenoxy-




oil, IR [cm


−1


] (Film)










but-1-yl




755, 891, 980, 1037,











1245, 1498, 1525,











1600, 1674, 2939,











3350, 3410






I.64




H




CH


3






CH


3






2-(2′-Fluoro-




oil, IR [cm


−1


] (Film)










phenoxy)eth-1-yl




749, 889, 924, 979,











1037, 1260, 1366,











1507, 1524, 1673,











2930, 3340, 3410






I.65




H




CH


3






CH


3






3-(2′-Fluoro-




oil, IR [cm


−1


] (Film)










phenoxy)-prop-1-




749, 979, 1037,










yl




1204, 1260, 1280,











1366, 1507, 1524,











1675, 2930, 3340,











3420






I.66




H




CH


3






CH


3






E-4-(2′-Fluoro-




oil, IR [cm


−1


] (Film)










phenoxy)-but-1-




749, 891, 980, 1037,










yl




1205, 1259, 1366,











1507, 1524, 1675,











2930, 3340, 3420






I.67




H




CH


3






CH


3






6-(4′-Chloro-




m.p.: 58-62° C.










phenoxy)-hex-1-










yl






I.68




H




CH


3






CH


3






2-(4′-Chloro-




oil, IR (cm


−1


] (Film)










phenoxy)-prop-1-




885, 979, 1007, 1037,










yl




1091, 1241, 1366,











1490, 1525, 1674,











2930, 3340, 3420






I.69




H




CH


3






CH


3






C


6


H


5


—C


2


H


4


—O—C


2


H


4


—




oil, IR [cm


−1


] (Film)











893, 920, 979, 1038,











1092, 1124, 1365,











1524, 1674, 2937,











3350, 3420






I.70




H




CH


3






CH


3






E-4-(3′-Methoxy-




oil, IR [cm


−1


] (Film)










phenyl)-but-3-




890, 978, 1038, 1156,










en-1-yl




1365, 1525, 1579,











1598, 1675, 2937,











3320, 3390






I.71




H




CH


3






CH


3






E-4-(4′-Fluoro-




m.p.: 77-81° C.










phenyl)-but-3-










en-1-yl






I.72




H




CH


3






CH


3






(3-Bromoisoxazol-




IR [cm


−1


] (Film)










5-yl)-methyl




769, 889, 904, 951,











988, 1001, 1035,











1359, 1526, 1677,











3420






I.73




H




CH


3






CH


3






(3-CF


3


-isoxazol-




IR [cm


−1


] (KBr)










5-yl)-methyl




769, 893, 987, 999,











1034, 1150, 1192,











1221, 1674, 3430






I.74




H




CH


3






CH


3






(3-iso-Propyl-




oil, IR [cm


−1


] (Film)










isoxazol-5-yl)-




883, 900, 980, 1000,










methyl




1036, 1366, 1525,











1673, 2937, 2968,











3340






I.75




H




CH


3






CH


3






(3-Cyclopropyl-




oil, IR [cm


−1


] (Film)










isoxazol-5-yl)-




883, 907, 980, 1000,










methyl




1036, 1366, 1434,











1526, 1608, 1673,











2930, 3340






I.76




H




CH


3






CH


3






(3-iso-Propyl-




oil, IR [cm


−1


] (Film)










1,2,4-Oxadiazol-




882, 979, 1019, 1037,










5-yl)-methyl




1091, 1366, 1525,











1674, 2938, 2972,











3340













I.77




H




CH


3






CH


3


















m.p.: 160-165° C.













I.78




H




CH


3






4-OCH


3


—C


6


H


4






CH


3






m.p.: 121-125° C.






I.79




H




CH


3






4-OCH


3


—C


6


H


4






C


2


H


5






oil, IR [cm


−1


] (Film)











922, 979, 1036, 1091,











1176, 1252, 1512,











1608, 1675, 2937,











3340






I.80




H




CH


3






4-OCH


3


—C


6


H


4






n-C


3


H


7






oil, IR [cm


−1


] (Film)











979, 1037, 1067,











1176,











1252, 1512, 1608,











1676, 2936, 2965,











3350






I.81




H




CH


3






4-OCH


3


—C


6


H


4






i-C


3


H


7






oil, IR [cm


−1


] (Film)











977, 1037, 1122,











1174,











1252, 1512, 1608,











1676, 2937, 2974, 3340






I.82




H




CH


3






4-OCH


3


—C


6


H


4






n-C


4


H


9






oil, IR [cm


−1


] (Film)











835, 978, 1035, 1176,











1252, 1512, 1608,











1675, 2936, 2958,











3340






I.83




H




CH


3






4-OCH


3


—C


6


H


4






t-C


4


H


9






IR [cm


−1


] (Film)











958, 979, 1036, 1174,











1191, 1253, 1364,











1513, 1609, 1678,











2930, 2970, 3420













I.84




H




CH


3






C


6


H


5


















m.p.: 120-124° C.













I.85




H




CH


3






C


6


H


5






3-Fluorobenzyl




oil, IR [cm


−1


] (Film)











695, 919, 979, 1002,











1036, 1447, 1488,











1525, 1591, 1676,











2920, 3330, 3410






I.86




H




CH


3






C


6


H


5






3-Bromobenzyl




oil, IR [cm


−1


] (Film)











696, 776, 979, 1002,











1036, 1069, 1092,











1445, 1524, 1676,











2920, 3330, 3400






I.87




H




CH


3






C


6


H


5






3-CF


3


-Benzyl




oil, IR [cm


−1


] (Film)











979, 1003, 1036,











1074, 1125, 1166,











1201, 1330, 1525,











1676, 2920, 3330






I.88




H




CH


3






C


6


H


5






4-Chlorophenyl




m.p. 58-62° C.






I.89




H




CH


3






C


6


H


5






3,4-Dichloro-




oil, IR [cm


−1


] (Film)










benzyl




693, 880, 919, 979,











1002, 1035, 1445,











1471, 1525, 1676,











2930, 3340, 3420






I.90




H




CH


3






CH


3






2-Methoxy-




oil; IR [cm


−1


] (Film)










eth-1-yl




891, 919, 980, 1038,











1093, 1127, 1366,











1525, 1673, 2870,











2937, 3340






I.91




H




CH


3






4-Cl—C


6


H


4






CH


3






oil; IR [cm


−1


] (Film)











875, 894, 979, 1012,











1037, 1091, 1491,











1525, 1674, 2890,











2938, 3340






I.92




H




CH


3






4-Cl—C


6


H


4






C


2


H


5






oil; IR [cm


−1


] (Film)











924, 979, 1012, 1037,











1091, 1491, 1526,











1673, 2938, 2976,











3340






I.93




H




CH


3






4-Cl—C


6


H


4






n-C


3


H


7






oil; IR [cm


−1


] (Film)











979, 1012, 1038,











1067, 1092, 1491,











1525, 1675, 2937,











2967, 3340






I.94




H




CH


3






4-Cl—C


6


H


4






i-C


3


H


7






oil; IR [cm


−1


] (Film)











977, 1016, 1038,











1091, 1121, 1370,











1490, 1525, 1675,











2930, 2975, 3340






I.95




H




CH


3






4-Cl—C


6


H


4






n-C


4


H


9






oil; IR [cm


−1


] (Film)











979, 1012, 1037,











1070, 1091, 1491,











1525, 1674, 2936,











2959, 3330






I.96




H




CH


3






4-Cl—C


6


H


4






t-C


4


H


9






m.p.: 67-71° C.






I.97




H




CH


3






4-Cl—C


6


H


4






n-C


6


H


13






oil; IR [cm


−1


] (Film)











979, 1011, 1038,











1091, 1491, 1525,











1675, 2872, 2934,











2954, 3330






I.98




H




CH


3






4-Cl—C


6


H


4






3-Methyl-




oil; IR [cm


−1


] (Film)










but-2-en-1-yl




833, 878, 979, 1038,











1091, 1447, 1491,











1525, 1675, 2937,











3330






I.99




H




CH


3






4-Cl—C


6


H


4






Propargyl




m.p.: 109-114° C.






I.100




H




CH


3






4-F—C


6


H


4






CH


3






m.p.: 130-132° C.






I.101




H




CH


3






4-F—C


6


H


4






C


2


H


5






m.p.: 105-110° C.






I.102




H




CH


3






4-F—C


6


H


4






n-C


3


H


7






oil; IR [cm


−1


] (Film)











840, 979, 1038, 1223,











1508, 1523, 1605,











1673, 2937, 2967,











3360






I.103




H




CH


3






4-F—C


6


H


4






i-C


3


H


7






oil; IR [cm


−1


] (Film)











840, 978, 1038, 1122,











1158, 1224, 1509,











1525, 1675, 2930,











2975, 3340






I.104




H




CH


3






4-F—C


6


H


4






t-C


4


H


9






m.p.: 95-100° C.






I.105




H




CH


3






4-F—C


6


H


4






n-C


4


H


9






oil; IR [cm


−1


] (Film)











840, 979, 1013, 1037,











1224 1509, 1524,











1675 2936, 2959,











3340






I.106




H




CH


3






4-F—C


6


H


4






n-C


6


H


13






oil; IR [cm


−1


] (Film)











840, 979, 1011, 1038,











1225, 1509, 1524,











1605, 1676, 2935,











3340






I.107




H




CH


3






4-F—C


6


H


4






3-Methyl-




oil; IR [cm


−1


] (Film)










but-2-en-1-yl




841, 980, 1038, 1159,











1224, 1509, 1525,











1605, 1675, 2938,











3350






I.108




H




CH


3






4-F—C


6


H


4






Propargyl




oil; IR [cm


−1


] (Film)











841, 875, 980, 1005,











1035, 1222, 1509,











1525, 1602, 1674,











2110, 2930, 3250,











3340






I.109




H




CH


3






4-Cl—C


6


H


4






3-iso-Propyl-




oil; IR [cm


−1


] (Film)










1,2,4-oxadiazol-




874, 980, 1011, 1038,










5-yl)-methyl




1092, 1491, 1525,











1588, 1676, 2940,











2973, 3350






I.110




H




CH


3






4-Cl—C


6


H


4






Thiazol-4-yl-




m.p.: 46-48° C.










methyl






I.111




H




CH


3






4-Cl—C


6


H


4






(3-iso-Propyl-




oil; IR [cm


−1


] (Film)










isoxazol-




981, 999, 1013, 1036,










5-yl)-methyl




1092, 1491, 1526,











1675, 2938, 2968,











3340






I.112




H




CH


3






4-Cl—C


6


H


4






(3-Bromo-isoxazol-




m.p.: 46-49° C.










5-yl)-methyl






I.113




H




CH


3






4-Cl—C


6


H


4






(3-CF


3


-isoxazol-




oil; IR [cm


−1


] (Film)










5-yl)-methyl




970, 980, 999, 1013,











1036, 1092, 1155,











1190, 1491, 1671,











2940, 3340






I.114




H




CH


3






3-Cl—C


6


H


4






CH


3






m.p.: 117-120° C.






I.115




H




CH


3






C


2


H


5






CH


3






m.p.: 74-77° C.






I.116




H




CH


3






C


2


H


5






C


2


H


5






oil; IR [cm


−1


] (Film)











768, 926, 960, 975,











1021, 1041, 1053,











1654, 1671, 2970,











3296






I.117




H




CH


3






4-CH


3


—C


6


H


4






CH


3






oil; IR [cm


−1


] (Film)











980, 1006, 1037,











1092, 1447, 1461,











1528, 1669, 2939,











3349






I.118




H




CH


3






4-CH


3


—C


6


H


4






C


2


H


5






oil; IR [cm


−1


] (Film)











923, 954, 980, 1037,











1091, 1447, 1528,











1669, 2938, 2976,











3340






I.119




H




CH


3






4-CH


3


—C


6


H


4






n-C


3


H


7






oil; IR [cm


−1


] (Film)











911, 979, 1039, 1067,











1092, 1458, 1525,











1673, 2936, 2965,











3340






I.120




H




CH


3






3-Cl—C


6


H


4






C


2


H


5






oil; IR [cm


−1


] (Film)











924, 979, 1012, 1037,











1091, 1411, 1525,











1673, 2937, 2976,











3350






I.121




H




CH


3






3-Cl—C


6


H


4






n-C


3


H


7






oil; IR [cm


−1


] (Film)











917, 980, 1038, 1067,











1093, 1411, 1525,











1673, 2937, 2966,











3340






I.122




H




CH


3






3-Cl—C


6


H


4






i-C


3


H


7






oil; IR [cm


−1


] (Film)











979, 1038, 1093,











1121, 1370, 1412,











1526, 1673, 2937,











2975, 3340






I.123




H




CH


3






3-Cl—C


6


H


4






n-C


4


H


9






oil; IR [cm


−1


] (Film)











882, 979, 1037, 1071,











1092, 1412, 1525,











1674, 2936, 2959,











3350






I.124




H




CH


3






3-Cl—C


6


H


4






3-Chloro-




oil; IR [cm


−1


] (Film)










prop-2-en-1-yl




789, 880, 932, 960,











1006, 1037, 1092,











1412, 1525, 1675,











2930, 3420






I.125




H




CH


3






3-Cl—C


6


H


4






Propargyl




oil; IR [cm


−1


] (Film)











695, 885, 927, 980,











1006, 1035, 1092,











1412, 1525, 1674,











2110, 2930, 3290






I.126




H




CH


3






2-Cl—C


6


H


4






CH


3






m.p.: 160-162° C.






I.127




H




CH


3






2-Cl—C


6


H


4






C


2


H


5






m.p.: 125-127° C.






I.128




H




CH


3






2-Cl—C


6


H


4






n-C


3


H


7






m.p.: 102-103° C.






I.129




H




CH


3






3-CH


3


-isoxazol-




CH


3






oil; IR [cm


−1


] (Film)









5-yl





3345 2940, 1675,











1526, 1446, 1412,











1068, 1038, 979, 959,











897






I.130




H




CH


3






3-CH


3


-isoxazol-




C


2


H


5






oil; IR [cm


−1


] (Film)









5-yl





3340, 2939, 1675,











1526, 1446, 1412,











1091, 1037, 980, 957,











921






I.131




H




CH


3






3-CH


3


-isoxazol-




n-C


3


H


7






oil; IR [cm


−1


] (Film)









5-yl





3350, 2938, 1675,











1526, 1447, 1412,











1068, 1037, 1011,











980, 960






I.132




H




CH


3






3-CH


3


-isoxazol-




i-C


3


H


7






oil; IR [cm


−1


] (Film)









5-yl





3345, 2977, 2938,











1675, 1527, 1412,











1371, 1119, 1037,











982, 949






I.133




H




CH


3






3-CH


3


-isoxazol-




n-C


4


H


9






oil; IR [cm


−1


] (Film)









5-yl





3340, 2959, 2937,











1676, 1526, 1447,











1412, 1071, 1036,











980, 951






I.134




H




CH


3






3-CH


3


-isoxazol-




n-C


6


H


13






oil; IR [cm


−1


] (Film)









5-yl





3340, 2935, 1676,











1526, 1447, 1412,











1092, 1037, 1016,











980, 958






I.135




H




CH


3






3-CH


3


-isoxazol-




Prop-1-en-3-yl




oil; IR [cm


−1


] (Film)









5-yl





3345, 2935, 1675,











1527, 1446, 1413,











1092, 1036, 1014,











981, 942, 919






I.136




H




CH


3






3-CH


3


-isoxazol-




(E)-1-Chloro-




oil; IR [cm


−1


] (Film)









5-yl




prop-1-en-3-yl




3340, 2938, 1674,











1527, 1446, 1412,











1092, 1036, 1014,











981, 949






I.137




Cl




CH


3






CH


3






CH


3






m.p.: 120-122° C.






I.138




Cl




CH


3






C


6


H


5






CH


3






m.p.: 190-192° C.






I.139




Cl




CH


3






C


6


H


5






C


2


H


5






oil; IR [cm


−1


] (Film)











1039, 1444, 1528,











1676, 2038, 3350






I.140




H




SCH


3






CH


3






CH


3






oil; IR [cm


−1


] (Film)











3340, 1671, 1526,











1094, 1074, 1039,











1014, 980, 957, 877






I.141




H




SCH


3






CH


3






C


2


H


5






oil; IR [cm


−1


] (Film)











3335, 2936, 1672,











1526, 1442, 1411,











1365, 1092, 1039,











981, 884






I.142




H




SCH


3






CH


3






n-C


3


H


7






oil; IR [cm


−1


] (Film)











3340, 2965, 2936,











1672, 1526, 1365,











1094, 1064, 1037,











981, 960






I.143




H




SCH


3






CH


3






i-C


3


H


7






oil; IR [cm


−1


] (Film)











3340, 2958, 2935,











2871, 1672, 1526,











1436, 1365, 1093,











1037, 980






I.144




H




SCH


3






CH


3






n-C


6


H


13






oil; IR [cm


−1


] (Film)











3340, 2954, 2933,











2871, 1672, 1526,











1436, 1365, 1093,











1037, 980






I.145




H




SCH


3






CH


3






Prop-1-en-3-yl




oil; IR [cm


−1


] (Film)











3340, 2935, 1672,











1526, 1412, 1094,











1036, 980, 959, 923,











871






I.146




H




SCH


3






CH


3






3-CF


3


—C


6


H


4


—CH


2






oil; IR [cm


−1


] (Film)











3340, 2930, 1673,











1528, 1330, 1165,











1125, 1098, 1074,











1038, 982






I.147




H




CH


3






3-Pyridyl




CH


3






oil; IR [cm


−1


] (Film)











3340, 2939, 1672,











1526, 1412, 1071,











1038, 1005, 979, 896,











873






















TABLE II










































No.




R


2




m






R


3






R


4






R


5






Data









II.01




H




CH


3






p-OCH


3


—C


6


H


4






CH


3






oil, IR [cm


−1


] (Film)











834, 977, 1027, 1065,











1175, 1251, 1358,











1512, 1175, 1608,











2936, 3330






II.02




H




CH


3






p-OCH


3


—C


6


H


4






n-C


3


H


7






oil, IR [cm


−1


] (Film)











977, 1027, 1066, 1176,











1251, 1358, 1512,











1607, 2935, 2964,











3340






II.03




H




CH


3






p-OCH


3


—C


6


H


4






n-C


4


H


9






oil, IR [cm


−1


] (Film)











834, 975, 1027, 1175,











1252, 1359, 1512,











1607, 2934, 2957,











3340






II.04




H




CH


3






C


6


H


5






3-Fluoro-




m.p. 142-150° C.










benzyl






II.05




H




CH


3






C


6


H


5






3-CF


3


-benzyl




oil, IR [cm


−1


] (Film)











701, 1027, 1073, 1100,











1125, 1166,











1201, 1329, 1361,











1519, 2920, 3340






II.06




H




CH


3






C


6


H


5






3,4-Dichloro-




oil, IR [cm


−1


] (Film)










benzyl




694, 769, 877, 893,











975, 1028, 1357,











1471, 1519, 2935,











3340






II.07




H




CH


3






C


6


H


5






4-Chloro-




m.p. 55-60° C.










phenyl






II.08




H




CH


3






C


6


H


5






3-Bromobenzyl




oil, IR [cm


−1


] (Film)











696, 773, 876, 893,











975, 1028, 1064,











1358, 1519, 2935,











3350






II.09




H




CH


3






4-Cl—C


6


H


4






i-C


3


H


7






oil, IR [cm


−1


] (Film)











942, 974, 1027, 1091,











1121, 1358, 1369,











1490, 1518, 2920,











2975, 3350






II.10




H




CH


3






4-Cl—C


6


H


4






n-C


4


H


9






oil, IR [cm


−1


] (Film)











830, 976, 1027, 1091,











1358, 1490, 1518,











2934, 2958, 3350






II.11




H




CH


3






4-Cl—C


6


H


4






t-C


4


H


9






oil, IR [cm


−1


] (Film)











894, 973, 1030, 1089,











1188, 1364, 1490,











1519, 2934, 2977, 3350






II.12




H




CH


3






4-Cl—C


6


H


4






n-C


6


H


13






oil, IR [cm


−1


] (Film)











830, 977, 1027, 1091,











1357, 1490, 1518,











2871, 2932, 2954, 3350






II.13




H




CH


3






4-F—C


6


H


4






C


2


H


5






oil, IR [cm


−1


] (Film)











841, 976, 1027, 1058,











1225, 1358, 1509,











2936, 2970, 3360






II.14




H




CH


3






4-F—C


6


H


4






n-C


3


H


7






oil, IR [cm


−1


] (Film)











840, 978, 1027, 1065,











1225, 1359, 1508,











1604, 2936, 2966, 3360






II.15




H




CH


3






4-F—C


6


H


4






t-C


4


H


9






m.p.: 113-119° C.














Examples of the action against harmful fungi;




It was possible to show the fungicidal action of the compounds of the general formula I by the following tests:




The active compounds were prepared as a 20% strength emulsion in a mixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, wetting agent having emulsifying and dispersant action based on ethoxylated alkylphenols) and 10% by weight of Emulphor® EL (Emulan® EL, emulsifier based on ethoxylated fatty alcohols) and correspondingly diluted to the desired concentration with water.




1.


Erysiphe graminis


var.


tritici






Leaves of wheat seedlings (Kanzler variety) were first treated with the aqueous preparation of the active compounds (containing 250 ppm). After about 24 h, the plants were dusted with spores of powdery mildew of wheat (


Erysiphe graminis


var.


tritici


). The plants treated in this way were then incubated for 7 days at 20-22° C. and a relative atmospheric humidity of 75-80%. The extent of fungal development was then determined.




In this test, the plants treated with the compounds according to the invention showed an attack of 5% or less, the plants treated with a known active compound (compound No. 195, Table 3, EP-A 463 488) showed 25% attack and the untreated plants showed 70% attack.




In a corresponding test (wheat seedlings of the Kanzler variety, application rate 250 ppm), the plants were first infected and incubated and then treated with the active compounds. In this test, the plants treated with the compounds according to the invention showed an attack of 5% or less and the untreated plants showed 60% attack.




Examples of the action against animal pests:




It was possible to show the insecticidal action of the compounds of the general formula I by the following tests:




The active compounds were prepared




a) as a 0.1% strength solution in acetone or




b) as a 10% strength emulsion in a mixture of 70% by weight of cyclohexanol, 20% by weight of Nekanil® LN (Lutensol® AP6, wetting agent having emulsifying and dispersant action based on ethoxylated alkylphenols) and 10% by weight of Emulphor®EL (Emluan®EL, emulsifier based on ethoxylated fatty alcohols)




and correspondingly diluted to the desired concentration with acetone in the case of a) or with water in the case of b).




After termination of the tests, in each case the lowest concentration was determined at which the compounds still caused an 80-100% inhibition or mortality in comparison to untreated control tests (action threshold or minimum concentration).






Aphis fabae


(black fly), contact action




Heavily infested dwarf beans (


Vicia faba


) were treated with the aqueous active compound preparation. The mortality rate was determined after 24 h.




In this test, the compounds I.68, I.69, I.70, I.71, I.81, I.86, I.94, I.97, I.103, I.105, I.106, II.12 and II.13 according to the invention showed action thresholds of 400 ppm or less.




Nephotettix cincticeps (green rice leaf hopper), contact action




Circular filters were treated with the aqueous active compound preparation and then occupied by 5 adult leaf hoppers. The mortality was assessed after 24 h.




In this test, the compounds I.02, I.04, I.10, I.17, I.24, I.29, I.46, I.47, I.48, I.52, I.55, I.74, I.75, I.78, I.79 and I.92 according to the invention showed action thresholds of 0.4 mg or less.






Prodenia litura


(Egyptian cotton leaf worm), contact action




Filters treated with the aqueous active compound preparation were occupied by 5 caterpillars. The first assessment is carried out after 4 h. If at least one caterpillar is still living, a feed mixture is added. The mortality was determined after 24 h.




In this test, the compounds I.04, I.17, I.78, I.79, I.91, I.92, I.94, I.101, I.102, I.103 and I.108 according to the invention showed action thresholds of 0.4 mg or less.






Tetranychus telarius


(common red spider mite), contact action




Potted dwarf beans having the second successive pair of leaves were treated with aqueous active compound preparation. After 24 h, the plants were infected using heavily infested pieces of leaf. The attack was determined after 12 days in the greenhouse.




In this test, the compounds I.37, I.91, I.92, I.93, I.97, I.101, I.102, I.104, I.105, I.106, I.108, II.13, II.14 and II.15 showed action thresholds of 400 ppm or less.



Claims
  • 1. A phenylacetic acid compound of the formula I where the substituents and the index have the following meanings:X is oxygen or sulfur; R is hydrogen and or C1-C4-alkyl; R1 is hydrogen and C1-C4-alkyl; R2 is cyano, nitro, trifluoromethyl, halogen, C1-C4-alkyl and or C1-C4-alkoxy; m is 0, 1 or 2, it being possible for the R2 radicals to be different if m is 2; R3 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylamino or di-C1-C4-alkylamino; R4 is C1-C6-alkyl, which is partly or completely halogenated or carries one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C2-C6-alkenyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C1-C4-alkoxy, arylthio, aryl-C1-C4-alkylthio, hetaryl, hetaryloxy, hetaryl-C1-C4-alkoxy, hetarylthio, hetaryl-C1-C4-alkylthio, it being possible for the cyclic radicals in turn to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C(═NOR6)—An—R7; or C3-C6-cycloalkyl, which is partly or completely halogenated or carries one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy; R5 is hydrogen, C1-C10-alkyl, C3-C6-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C10-alkylcarbonyl, C2-C10-alkenylcarbonyl, C3-C10-alkynylcarbonyl or C1-C10-alkylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the cyclic groups in turn to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(═NOR6)—An—R7; aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(═NOR6)—An—R7; A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C1-C6-alkyl; n is 0 or 1; R6 is hydrogen or C1-C6-alkyl and R7 is hydrogen or C1-C6-alkyl, or a salt thereof.
  • 2. The compound of the formula I defined in claim 1, whereinR3 is hydrogen, hydroxyl, cyclopropyl, halogen, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkylthio, and R5 is hydrogen, C1-C10-alkyl, C3-C6-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C10-alkylcarbonyl, C2-C10-alkenylcarbonyl, C3-C10-alkynylcarbonyl or C1-C10-alkylsulfonyl, it being possible for these groups to be partly or completely halogenated or to carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the aromatic and heteroaromatic radicals, in turn, to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, halogen, aminothiocarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(═NOR6)—An—R7; or aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl or hetarylsulfonyl, it being possible for these groups to be partly or completely halogenated or to carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(═NOR6)—An—R7; or a salt thereof.
  • 3. The compound of the formula I defined in claim 1, wherein m is 0.
  • 4. The A compound of the formula I defined in claim 1, wherein R1 is methyl.
  • 5. The compound defined in claim 1, wherein R4 denotes C1-C6-alkyl, which is partly or completely halogenated or carries one to three of the following radicals: cyano, hydroxyl, halogen, C1-C6-alkoxy, C3-C6-cycloalkyl, heterocyclyl, aryl, aryloxy, hetaryl and hetaryloxy, or C3-C6-cycloalkyl, which is partly or completely halogenated or carries one to three of the following groups: halogen, C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxy.
  • 6. The compound defined in claim 1, wherein R4 denotes C1-C6-alkyl, which is partly or completely halogenated or carries one to three of the following radicals: halogen and C1-C6-alkoxy.
  • 7. A process for preparing a compound of the formula I as defined in claim 1, wherein R3 is not halogen, which comprises reacting a benzyl compound of the formula II wherein L1 is a nucleophilically replaceable leaving group, with a hydroxyimine of the formula IIIR5ON═C(R4)—C(R3)═NOH   (III).
  • 8. A process for preparing a compound of the formula I as defined in claim 1, wherein R3 is not halogen, which comprises reacting a benzyl compound of the formula II with a dihydroxyimine of the formula IVHON═C(R4)—C(R3)═NOH   (IV) to give a compound of the formula Vand then reacting V with a compound of the formula VIR5—L2   (VI) wherein L2 is a nucleophilically replaceable leaving group, to give I.
  • 9. A process for preparing a compound of the formula I defined in claim 1, wherein R3 is not halogen, which comprises reacting a benzyl compound of the formula II with a carbonylhydroxyimine of the formula VIIO═C(R4)—C(R3)═NOH   (VII) to give a compound of the formula VIII then either reacting VIIIa) first with hydroxylamine or its salt and then with a compound of the formula VI R5—L2   (VI) orb) with a hydroxylamine or a hydroxylammonium salt of the formula IXa or IXb R5ONH2   (IXa) R5ONH3⊕Q⊖  (IXb) where Q⊖ is the anion of an acid, to give I.
  • 10. A composition against animal pests or harmful fungi, comprising customary additives and an effective amount of a compound of the formula I defined in claim 1.
  • 11. A method for controlling animal pests or harmful fungi, which comprises treating the pests or harmful fungi, their environment or the plants, surfaces, materials or spaces to be kept free from said pests or fungi with an effective amount of a compound of the formula I defined in claim 1.
Priority Claims (2)
Number Date Country Kind
44 03 448 Feb 1994 DE
44 21 182 Jun 1994 DE
Parent Case Info

This is a Divisional Application of application Ser. No. 09/334,385, filed Jun. 16, 1999 (now U.S. Pat. No. 6,100,263), which is a Divisional Application of application Ser. No. 09/015,692, filed Jan. 29, 1998 (now U.S. Pat. No. 5,981,581), which is a Divisional Application of application Ser. No. 08/687,480, filed on Aug. 5, 1996 (now U.S. Pat. No. 5,889,059), which was filed under 35 U.S.C. 371 as a National Stage application of International Application No. PCT/EP 95/00,007, filed on Jan. 3, 1995.

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Number Name Date Kind
5194662 Brandt et al. Mar 1993
5221691 Clough et al. Jun 1993
5393782 Wingert et al. Feb 1995
5756426 Ziegler et al. May 1998
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Number Date Country
2104806 Mar 1994 CA
398692 Nov 1990 EP
567828 Apr 1992 EP
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528682 Feb 1993 EP
9007493 Jul 1990 WO
9426700 Nov 1994 WO
9518789 Jul 1995 WO
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Entry
Pat. Abstr. of Japan, vol. 17, No. 644 (C-1134) (English abstract of JP-A 05/201,946, Aug. 10, 1993).
Pat. Abstr. of Japan, vol. 18, No. 19 (C-1152) (English abstract of JP-A 05/255,012, May 10, 1993).
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