HUT76523A - Phenylthio acetic acid derivatives, intermediates, preparation and use thereof, fungicide and insecticid compositions containing these compounds as active ingredients - Google Patents

Description

FIELD OF THE INVENTION The present invention relates to phenylthioacetic acid derivatives of the formula I, their salts, processes for their preparation, intermediates obtained therefrom, compositions for the control of animal pests and fungi containing the compounds of the formula I as active ingredients. use for this purpose.

In the formula (I), the index value and the substituents have the following meanings:

R 1 is hydrogen, C 1-4 alkyl;

R ² is halogen, cyano, nitro, trifluoromethyl, C 1-4 alkyl or C 1-4 alkoxy;

d m is 0, 1 or 2; and when m is 2, the two Rs may be different from each other;

R ³ is hydrogen, halogen, cyano, nitro, hydroxy, amino, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, C 1-4 haloalkoxy -

C 1-4 alkylthio, C 1-4 alkylamino, or C 1-4 dialkylamino per alkyl moiety;

R is hydrogen, halogen, cyano, nitro, hydroxy, amino, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylthio, C 1-6 alkylamino- , C1-C6 dialkylamino, C2-C6 alkenyl, C2-C6 alkenyloxy, C2-C6 alkenylthio, C2-C6 alkenylamino, in the alkenyl moiety 2-6 and in the alkyl moiety C 1 -C 6 N-alkenyl-N-alkylamino, C 2 -C 6 alkynyl, C 2 -C 6 alkyloxy, C 2 -C 6 alkynylthio, C 2 -C 6 alkynyl amino - either the N-alkynyl-N-alkylamino group having 2 to 6 carbon atoms in the alkynyl moiety and the alkyl moiety having 1 to 6 carbon atoms in which the hydrocarbon group may be partially or fully halogenated, or the hydrocarbon group may be substituted by one to three groups: halogen, cyano, nitro, hydroxy, mercapto, amino, carboxy, carbamoyl, thiocarbamoyl, C 1 -C 6 alkylcarbamoyl, in the alkyl moiety e.g. C 1-6 dialkylcarbamoyl, C 1-6 alkylthiocarbamoyl, C 1-6 dialkylthiocarbamoyl, C 1-6 alkylsulfonyl, C 1-6 alkylsulfinyl, 1 -C 6 alkoxy,

C 1-6 haloalkoxy; C 1-6 alkoxycarbonyl; C 1-6 alkylthio; C 1-6 alkylamino; C 1-6 dialkylamino; C 6 -C 6 alkenyloxy, C 3 -C 6 cycloalkyl,

C3-6cycloalkyloxy, heterocyclyl, heterocyclyl linked through an oxygen atom, aryl, aryloxy, C 1-4 arylalkoxy in the alkoxy moiety, C 1-4 aryl in the alkyl moiety alkylthio, heteroaryl, heteroaryloxy, C 1 -C 4 heteroaryl-alkoxy, heteroarylthio, alkyl-C 1 -C 4 heteroarylalkylthio, wherein the ring moiety is partially or may be fully halogenated and / or the ring moiety may be substituted by one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxy, carbamoyl, thiocarbamoyl, C 1-6 alkyl -, C 1-6 haloalkyl, C 1-6 alkylsulfonyl, C 1-6 alkylsulfinyl, C 3-6 cycloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, C 1-6 alkoxycarbonyl, C 1-6 alkylthio, 1-6 s in the alkoxy moiety alkylene amino, C 1-6 alkylalkylcarbamoyl alkyl, C 1-6 alkylcarbamoyl alkyl, C 1-6 dialkylcarbamoyl alkyl, C 1-6 alkylthiocarbamoyl alkyl

C1-6 dialkylthiocarbamoyl, C2-6 alkenyl,

C 2 -C 6 alkenyl-benzyl, benzyl, benzyloxy, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy, heteroarylthio and -C (= NOR ⁶ ) -A _n -R ⁷ group;

C3-6cycloalkyl, C3-6cycloalkyloxy, C3-6cycloalkylthio, C3-6cycloalkylamino, C3-6cycloalkyl and N-cycloalkyl1-6alkyl -N-alkylamino, C3-6cycloalkenyl, C3-6cycloalkenyloxy, C3-6cycloalkenylthio, C3-6cycloalkenylamino, 3-6 in the cycloalkenyl and alkyl C 1 -C 6 N-cycloalkenyl-N-alkylamino, heterocyclyl, heterocyclic group bonded via oxygen, sulfur or ammonia, C 1 -C 6 alkyl substituted by heterocyclic nitrogen atom, aryl, aryloxy, aryl -thio, arylamino, C 1-6 alkyl in the alkyl moiety, N-aryl-N-alkylamino, heteroaryl, heteroaryloxy, heteroarylthio, heteroarylamino, in the alkyl moiety of 1-6 carbon atoms N-heteroaryl-N-alkylamino, wherein the ring moiety may be partially or fully halogenated or substituted the substituent may be substituted by one to three of the following groups: halogen, cyano, nitro, hydroxy, mercapto, amino, carboxy, carbamoyl, thiocarbamoyl, C 1-6 alkyl -, C 1-6 haloalkyl, C 1-6 alkylsulfonyl, C 1-6 alkylsulfinyl, C 3-6 cycloalkyl, - C 1-6 alkoxy,

C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino, C 1 -C 6 alkylalkyl per alkyl, in the alkyl moiety C 1-6 alkylcarbamoyl, per alkyl moiety

C 1 -C 6 dialkylcarbamoyl, C 1 -C 6 alkylthiocarbamoyl, C 1 -C 6 dialkylthiocarbamoyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyl-OX 1 -, benzyl ·, benzyl, aryl, aryloxy, heteroaryl and heteroaryloxy;

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 in the alkyl moiety, and 2 to 10 carbon atoms in the alkenyl moiety. C 3 -C 10 alkynylcarbonyl, C 3 -C 10 alkynylcarbonyl or C 1 -C 10 alkylsulfonyl groups which may be partially or fully halogenated or which may be substituted by one to three of the following groups: halogen, cyano, nitro; , hydroxy, mercapto, amino, carboxy, carbamoyl, thiocarbamoyl, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkylsulfonyl, C 1-6 alkyl- sulfinyl, 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, alkyl in the alkoxy moiety C 1-6 dialkylamino, C 1-6 alkylcarbamoyl alkyl, C 1-6 alkyl per alkyl alkylcarbamoyl, the alkyl moiety contains C1 -C6 alkyl-thiocarbamoyl, C1 -C6 dialkylthiocarbamoyl, C2 -C6 alkenyl, C2 -C6 alkenoyloxy, C3 -C6 cycloalkyl,

C3-C6 cycloalkyloxy, heterocyclyl, heteroaryl-linked heterocyclyl, benzyl, benzyloxy, aryl, aryl-thio, arylthio, heteroaryl, heteroaryloxy and heteroarylthio in which the cyclic moiety may be partially or fully halogenated or may be substituted by one to three of the moieties selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxy, carbamoyl, thiocarbamoyl, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkylsulfonyl, C 1-6 alkylsulfinyl, C 3-6 cycloalkyl, C 1-6 alkoxy, 1- C 6 -C 6 haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, C 1 -C 6 -alkylamino in alkyl, and alkyl in 1 -C 6 -alkyl; C 6 alkylcarbamoyl, dialkylcarbamoyl C 1-6 alkyl, in the alkyl moiety

C 1 -C 6 alkylthiocarbamoyl, C 1 -C 6 dialkylthiocarbamoyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy arylthio, heteroaryl, heteroaryloxy, heteroarylthio and -C (= NOR) -A _n- R;

aryl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroarylcarbonyl or heteroarylsulfonyl groups which may be partially or fully halogenated or which may be substituted by one to three of the following groups: halogen, cyano, nitro -, hydroxy, mercapto, amino, carboxy, carbamoyl, thiocarbamoyl, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkylcarbonyl, 1-6 alkyl in the alkyl moiety C 1-6 -alkylsulfonyl, C 1-6 -alkylsulfinyl, C 3-6 -cycloalkyl, C 1-6 -alkoxy, C 1-6 -haloalkoxy, C 1-6 -alkoxycarbonyl in the alkoxy moiety, C 6 -C 6 alkylthio, C 1 -C 6 alkylamino, C 1-6 dialkylamino per pendent, C 1-6 alkylcarbamoyl in alkyl, C 1-6 dialkylcarbamoyl per pendant C 1 -C 6 alkylthiocarbamoyl, C 1 -C 6 dialkylthiocarbamoyl, C 2 -C 6 alkenyl, C 6 -C 6 alkenyloxy, benzyl, benzyl-OX 1, aryl, aryloxy, heteroaryl, heteroaryloxy and -C (= NOR ⁵ ) -A _n -R ⁷ ; in the formula

A is oxygen, sulfur or nitrogen to which is attached a hydrogen atom or a C 1-6 alkyl group;

n is 0 or 1;

R ^s is hydrogen or C1-6 alkyl;

R ⁷ is hydrogen or C 1-6 alkyl.

Phenylacetic acid derivatives for pest control are known in the art (see EP-A 432 503 and EP-A 463 448).

The object of the present invention was to find new compounds which have a better effect than before.

Accordingly, we have found phenylthioacetic acid derivatives of formula (I) as defined above. In addition, there has been found a process for their preparation, compositions containing the compounds of formula (I) as active ingredient, for the control of animal pests and pest fungi, and their use in this sense.

The compounds of formula (I) may be obtained in various ways by methods known per se from the literature.

In the synthesis of compounds of formula I, it is essentially irrelevant whether -C (= NOCH ₃ ) -C (= O) SR ¹ or -CH ₂ O N = C (R ^J ) -C (R ⁴ ) = N0R ^{5 is} first constructed.

The formation of the group -C (= NOCH ₃ ) -C (= O) SR ^{1 is} described, for example, in the literature cited above.

The synthesis of the side chain of the formula -CH ₂ O N = C (R ³ ) -C (R ⁴ ) = NO ⁵ R ⁵ is essentially based on the type of R ³ and R ⁴ substituents.

1. In the case where R ³ and R ⁴ are other than halogen, the formation of the group -CH ₂ ON = C (R ³ ) -C (R ⁴ ) = NO ^{5 is} generally carried out by the following formula (II): reacting a benzyl derivative of formula (III) with an oxime of formula (III); in formula (II), 1 / nucleophile is an exchangeable eliminable group, for example a halogen or sulfonate group, preferably a chlorine, bromine, iodine, methanesulfonate, p-toluenesulfonate or trifluoromethanesulfonate group.

The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base such as sodium hydride, potassium hydroxide, potassium carbonate or triethylamine according to the methods described by Houben-Weyl, Vol. and Volume 10/1, page 1189.

The oxime (III) required for the reaction is obtained by reacting the corresponding dioxime (IV) with a nucleophile substituted compound (VI), wherein in formula (VI), L represents a displaceable group on the nucleophile, for example a halogen atom or a sulfonate group, preferably chlorine. , bromine, iodine, methanesulfonate, p-toluenesulfonate or trifluoromethanesulfonate.

The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base such as sodium hydride, potassium hydroxide, potassium carbonate, pyridine or triethylamine according to the methods described by Houben-Weyl, Vol. , 307,

Pages 370 and 385; Volume 10/4, pages 55, 180, and 217;

E 5 volumes from page 780.

1.1 Alternatively, the compounds of formula (I) may be prepared by first reacting a benzyl derivative of formula (II) with a dioxime of formula (IV) to give the corresponding benzyloxime of formula (V) and then ) with a nucleophile substituted compound of formula (I) to give the corresponding compound of formula (I).

The reaction is carried out in a manner known per se, in an inert organic solvent, in the presence of a base such as sodium hydride, potassium hydroxide, potassium carbonate, pyridine or triethylamine, according to Houben-Weyl, 10/1. volume, from page 1189; Volume Eb 14b, pages 307, 370 and 385; 10/4 volumes,

Pages 55, 180, and 217; E 5 volumes from page 780.

1.2 Alternatively, the oxime of formula (III) required for the reaction may be obtained from the oxooxime of formula (VHa) by reaction with a hydroxylamine derivative of formula (IXa) or a salt of formula (IXb). In Formula IXb, Q represents an anion of an acid, especially an inorganic acid, such as a halide ion 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 and Houben-Weyl, Vol. Volume 14b, pages 369 and 385.

1.3 Alternatively, the compounds of formula (I) may also be prepared by reacting a benzyl derivative of formula (II) with an oxooxime of formula (VIIa) to give the corresponding benzyloxime of formula (VIII) and then ( Reaction with a hydroxylamine derivative of formula IXa or a salt of formula IXb.

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 or Houben-Weyl, Vol. E 14b, p. Volume 10/1,

Pages 1189 and 10/4 of pages 73.

1.4 Another possibility for the preparation of the compounds of the formula I is the reaction of the benzyl derivative of the formula II with N-hydroxyphthalimide and the hydrazinolysis of the resulting compound of the formula IIb to give the benzyloxy of the formula IIa. amine and reacting it with an oxo compound of formula X to give the desired compound of formula I.

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 Patent Application 42 28 867.3.

The oxo compound (X) required for the reaction is obtained, for example, by reacting the corresponding oxo oxime (VIIb) with a nucleophile substituted compound (VI) or the corresponding dioxo compound (XI) with a hydroxylamine derivative (IXa) or a salt of formula IXb.

The reaction is carried out in a manner known per se in an inert organic solvent according to the methods described in EP-A-513580; Houben-Weyl, Volume 10/4, pages 55, 73, 180 and 217; Volume 14b, pages 307 and 369; E 5 volumes from page 780.

1.5 Compounds of formula (I) may also be prepared by reacting a benzyloxyamine derivative of formula (IIa) with an oxooxime of formula (VIIIb) to obtain the corresponding benzyloxime of formula (V): from which, as above, is reacted with a nucleophile substituted compound of formula (VI) to provide the desired compound of formula (I).

1.6 By analogy, compounds of formula I can be prepared by reacting a benzyloxyamine derivative of formula Ha with a dioxo compound of formula XI to obtain benzyloxime of formula VIII, which is then reacting with a hydroxylamine derivative of formula IXa or a salt of formula IXb to give the desired compound of formula I.

2. Compounds of formula (I) wherein R ² and / or R ^{4 are} halogen are prepared from the corresponding starting compounds wherein the corresponding group is hydroxy; and this preparation reaction is carried out by methods known per se (see Houben-Weyl, Vol. E 5, p. 631; J. Org. Chem., 36, 233 (1971); J. Org. Chem., 57, 3245 (1922)]. The appropriate reaction is preferably used to prepare the halogen derivative of the formulas I and VIII.

3. Compounds of formula (I) wherein R ³ and / or R ^{4 are} attached to the side chain via an oxygen, sulfur or nitrogen atom are prepared from the corresponding starting compounds wherein the corresponding group represents a halogen atom; and this preparation reaction is carried out by methods known per se [see Houben-Weyl,

Ε 5 volumes, pages 826 and 1280; J. Org. Chem., 36, 233 (1971);

J. Org. Chem. 46, 3623 (1981)]. The starting materials for the reaction are preferably the halogen derivative (I) and (VIII).

4. Compounds of formula (I) wherein R and / or R are attached to the side chain via an oxygen atom are prepared in part from the corresponding starting compounds wherein the appropriate group is hydroxy; and this preparation reaction is carried out by methods known per se (see Houben-Weyl, Vol. E 5, 826-829). side; Aust. J. Chem. 27, 1341-1349 (1974)]. This reaction is preferably used to prepare the alkoxy derivatives of the formulas I and VIII.

5. Compounds of formula (I) wherein R ^J is other than halogen are preferably obtained by reacting compound (X) with a lactone of formula (XII) according to the process described in EP-A 493 711. converting the appropriately substituted benzoic acid of formula (XIII) to yield the compound of formula (XIV) via the corresponding acid halide, which is then reacted by the Pinner reaction [see Angew. Chem., 94, 1 (1982)] is converted to the α-ketoester of formula XV. The compound (XV) is "esterified" to give the corresponding thioester which is then converted to the compound (I).

6. A further process for preparing compounds of formula I comprises converting the keto group into an oxime ether group in the ketoester of formula XV and then ester group either directly via the carboxy group or after activation (e.g. by formation of carboxylic acid chloride). is converted to the corresponding thioester (see Organic, 16th Edition, 1985, pages 415, 423, and 622).

EP-A 432 503, EP-A 463 488 and EP-A 386 561 can be used to prepare compounds of formula II by the methods described.

The compounds of formula (I) are obtained on the basis of the double bond of C = C and C = N as E / Z isomeric mixtures which can be separated into their individual isomers by conventional means such as crystallization or chromatography.

If a mixture of isomers is formed during the synthesis, separation of the individual isomers is generally not necessary, since the individual isomers may be partially converted into one another during processing or application (for example, by exposure to light, acid or base). Suitable transformations can occur after application, for example, in the treatment of plants in treated plants or in the fungi or animal pests to be controlled.

For the double bond C = NOCH ₃ , the E isomers of the compounds of formula I are preferred for their activity (The methoxy group configuration is -0 (= 0) 313 ¹ ).

The cis isomers of the compounds of formula I are preferred for the double bond of formula -C (R ³ ) = NOCH 2 - (The configuration of R ^{3 is} relative to the group -OCH 2 -).

In the above definition of compounds of formula (I), generic terms are used to designate groups; for example, these groups are represented by the following unique groups:

halogen: fluorine, chlorine, bromine and iodine;

alkyl: straight-chain or branched alkyl groups having from 1 to 4, 10 or 1 to 10 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tertiary alkyl; butyl, pentyl, 1-, 2- and 3-methylbutyl, 1-ethyl-propyl, 1,1-, 1,2- and 2,2-dimethylpropyl, 1-, 2 -, 3- and

4-methylpentyl, 1,1-, 1,2-, 1,3-, 2,2-, 2,3- and 3,3-dimethylbutyl, 1- and 2-ethylbutyl- 1,1,2- and 1,2,2-trimethylpropyl,

1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

alkylamino: an amino group substituted by a straight or branched C 1 -C 6 alkyl group such as one of the foregoing groups;

dialkylamino group: an amino group substituted by two independently linear or branched alkyl groups having from 1 to 6 carbon atoms in the alkyl moiety, such that two of the groups mentioned above are independently substituted;

alkylcarbonyl: a linear or branched C 1 -C 10 alkyl group which is bonded to the parent compound through a carbonyl group (-C (= O) -);

alkylsulfonyl: a straight or branched alkyl group having 1 to 6 or 1 to 10 carbon atoms, which is bonded to the parent compound through a sulfonyl group (-S (= O) ₂ -).

···· alkylsulfmyl: a C 1 -C 6 straight or branched alkyl group bonded to the parent compound through a sulfinyl group (-S (= O) -);

alkylcarbamoyl group: a carbamoyl group (H ₂ N-CO-) substituted by a straight or branched C 1 -C 6 alkyl group such that one of the groups mentioned above is substituted;

dialylcarbamoyl: a carbamoyl group (H ₂ N-CO-) substituted by two alkyl groups of 1 to 6 carbon atoms per alkyl moiety, such that two of the groups mentioned above are substituted; alkyl-1-thiocarbamoyl: a thiocarbamoyl group (H ₂ N-CS-) substituted by a C 1-6 alkyl group such as one of the foregoing;

dialylthiocarbamoyl: a thiocarbamoyl group substituted by two alkyl groups having from 1 to 6 carbon atoms in the alkyl moiety, such that two of the groups mentioned above are substituted; haloalkyl: a linear or branched C 1 -C 6 alkyl group in which the hydrogen atoms are partially or completely substituted by halogen atoms, such as those mentioned above; for example, C 1-2 haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoride methyl, chloro-difluoromethyl, 1- and 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 group: straight or branched, 1-4 or

C 1-6 alkyl, such as one of the foregoing groups, which is attached to the parent compound through an oxygen atom (-O-); for example C 1-6 alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, 1-, 2- and 3-methyl butoxy, 1-ethylpropoxy, hexyloxy, 1,1-, 1,2- and 2,2-dimethylpropoxy, 1-, 2-, 3- and 4-methylpentyl-. oxy, 1,1, 1,2,

1,3-, 2,2-, 2,3- and 3,3-dimethylbutoxy, 1- and 2-ethylbutoxy,

1.1.2- and 1,2,2-trimethylpropoxy, i-ethyl-1-methylpropoxy and

1-ethyl-2-methyl-propoxy;

alkoxycarbonyl: a linear or branched C 1 -C 6 alkyl group attached to the parent compound through an oxycarbonyl group (-O-C (= O) -);

haloalkoxy: a straight or branched C 1 -C 6 alkyl group in which the hydrogen atoms are replaced in whole or in part by halogen atoms, such as those mentioned above, which are attached to the parent compound via an oxygen atom (-O-);

alkyl-tethered: straight or branched, 1-4 or

C 1-6 alkyl, such as one of the foregoing groups, which is bonded via a sulfur atom (-S-) to the parent compound, such as a C 1-6 alkylthio group such as methylthio, erthio, propylthio, isopropylthio, butylthio, sec-butylthio, isobutylthio, tert-butylthio, pentylthio, 1-, 2-and 3-methylbutylthio, 1-ethyl -propyl-thio, hexyl-thio, 1,1-,

1,2- and 2,2-dimethylpropylthio, 1-, 2-, 3- and 4-methylpentylthio, 1,1-, 1,2-, 1,3-, 2,2 -, 2,3- and 3,3-dimethylbutylthio,

1- and 2-ethylbunylthio, 1,1,2- and 1,2,2-trimethylpropylthio,

1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio; cycloalkyl: a monocyclic alkyl group containing from 3 to 6 carbon atoms as ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

alkenyl: a straight or branched C2-C6 or C2-C10 alkenyl group having a double bond at any position, such as a C2-C6 alkenyl group such as vinyl, 1-propenyl, allyl, 1-methylvinyl, 1-, 2- and 3-butenyl, 1- and 2-methyl-1-propenyl, 1- and 2-methylallyl, 1-, 2-,

3- and 4-pentenyl, 1-, 2- and 3-methyl-1-butenyl, 1-, 2- and 3-methyl-2-butenyl, 1-, 2- and 3-methyl-3 -butenyl, 1,1- and 1,2-dimethylallyl ·, 1,2-dimethyl-1-propenyl, 1-ethyl-1-propenyl, 1-ethylallyl, 1-, 2 -, 3-, 4- and 5-hexenyl, 1-, 2-, 3- and 4-methyl-1-pentenyl, 1-, 2-, 3- and 4-methyl-2-pentenyl, -, 2-, 3 and 4-methyl-3-pentenyl, 1-, 2-, 3- and 4-methyl-4-pentenyl, 1,2-,

1,3-, 2,3- and 3,3-dimethyl-1-butenyl, 1,1-, 1,2-, 1,3-, 2,3- and

3.3-dimethyl-2-burenyl, 1,1-, 1,2-, 1,3-, 2,2- and 2,3-dimethyl-3-butenyl, 1- and 2-ethyl-1-butenyl -, 1- and 2-ethyl-2-butenyl, 1 and 2-ethyl-3-butenyl ·, 1,1,2-trimethylallyl, 1-ethyl-1-methylallyl, 1-ethyl -2-methyl-1-propenyl and 1-ethyl-2-methylallyl;

alkenyloxy: a straight or branched alkenyl group having from 2 to 6 carbon atoms and having a double bond at any position, which is attached to the parent compound via an oxygen atom (-O-);

alkenylcarbonyl group: straight or branched carbon chain «·

C 2 -C 10 alkenyl having a double bond at any position which is attached to the parent compound via a carbonyl group (-C (= O) -);

alkenylthio or alkenylamino: a straight or branched alkenyl group having from 2 to 6 carbon atoms and having a double bond at any position which is attached to the parent compound via a sulfur atom (alkenylthio) or a nitrogen atom (alkenylamino);

alkynyl: a straight or branched chain alkynyl group having from 2 to 10 carbon atoms and having a triple bond at any position, such as a C 2-6 alkynyl group such as ethynyl, 2-propynyl, 2- and 3-butynyl, 1-methyl-2- propynyl, 2-, 3- and 4-pentynyl, 1-methyl-2-butynyl, 1- and 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl- 2-propynyl, 2-, 3-, 4- and 5-hexynyl, 1- and 4-methyl-2-pentyl, 1- and 2-methyl-3-pentynyl, 1-,

2- and 3-methyl-4-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-, 1,2- and

2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1- and 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

alkynylcarbon! swept: straight or branched chain,

An alkynyl group having from 3 to 10 carbon atoms and having a triple bond at any position which is attached to the parent compound via a carbonyl group (-C (-O) -);

alkynyloxy, alkynylthio and alkynylamino groups: a straight or branched alkynyl group having from 2 to 6 carbon atoms and having a triple bond at any position on an oxygen atom (alkynyloxy) or a sulfur atom (alkynylthio) or it is attached to the parent compound via a nitrogen atom (alkynylamino);

cycloalkyloxy, cycloalkylthio and cycloalkylamino: a monocyclic alkyl group containing from 3 to 6 carbon atoms as a ring member, such as cyclopropyl, cyclobutyl, cyclopentyloxy or cyclohexyl, on an oxygen atom (cycloalkyloxy) or a sulfur atom ( cycloalkylthio) or via a nitrogen atom (cycloalkylamino) to the parent compound;

cycloalkenyl, cycloalkenoxy, cycloalkenylthio and cycloalkenylammonium: a monocyclic alkenyl group containing from 3 to 6 carbon atoms as ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl or cyclohexenyl, directly (cycloalkenyl) or (cycloalkenyloxy) or via a sulfur atom (cycloalkenylthio) or a nitrogen atom (cycloalkenylamino);

heterocyclic group or a heterocyclic group attached through an oxygen, sulfur or nitrogen atom: a 3- to 6-membered, saturated or partially unsaturated, mono- or polycyclic group containing three heteroatoms from the group consisting of oxygen, nitrogen and sulfur; and which is bonded directly to the parent compound via an oxygen, sulfur or nitrogen atom, such as 2- and 3-tetrahydrofuryl, oxiranyl, 2- and 3-tetrahydro-thienyl, 2- and 3-pyrrolidinyl, 3-, 4- and 5-isoxazolidinyl, 3-, 4- and S-isothiazolidinyl,

3-, 4- and 5-pyrazolidinyl, 2-, 4- and 5-oxazolidinyl, 2-, 4- and

5-Thiazolidinyl, 2- and 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-oxa-diazolidin-2-yl, 1,3,4-thiadiazolidin-2- il-, 1,3,4-triazolidine

-2-ι1-, 2,3-dihydro-2-furyl, 2,3-dihydro-3-furyl, 2,3-dihydro

-4-furyl-2,3-dihydro-5-furyl, 2,5-dihydro-2-furyl, 2,5-dihydro-3-furyl, 2,3-dihydro-2-thienyl -, 2,3-dihydro-3-thienyl-2,3-dihydro-4-thienyl, 2,3-dihydro-5-thienyl, 2,5-dihydro-2

-thienyl, 2,5-dihydro-3-thienyl, 2,3-dihydro-2-pyrrolyl, 2,3-dihydro-3-pyrrolyl, 2,3-dihydro-4-pyrrolyl, 2 , 3-dihydro-5-pyrrolyl, 2,5-dihydro-2-pyrrolyl, 2,5-dihydro-3-pyrrolyl-2,3-dihydro-isoxazol-3-yl, 2,3-dihydro-isoxazol-4-yl -, 2,3-dihydroisoxazol-5-yl, 4,5-dinidroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2, 5-dihydroisothiazole-3

-yl, 2,5-dihydro-isothiazol-4-yl, 2,5-dihydro-isothiazol-5-yl-2,3-dihydro-isopyrazol-3-yl, 2,3-dihydro-isopyrazol-4-yl, 2,3-dihydro-isopyrazole -5-yl, 4,5-dihydro-isopyrazol-3-yl, 4,5-dihydro-isopyrazol-4-yl, 4,5-dihydro-isopyrazol-5-yl, 2,5-dihydro-isopyrazol-3-yl -, 2,5-dihydroisopyrazol-4-yl, 2,5-dihydroisoazazol-5-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl-2,3-dihydrooxazole -5-yl, 4,5-dihydrooxazol-3-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-3-yl2. 5-dihydrooxazol-4-yl, 2,5-dinidrooxazol-5-yl, 2,3-dihydro-thiazol-2-yl, 2,3-dihydro-thiazol-4-yl, 2,3-dihydro-thiazol-5-yl. -il-4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydro-thiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5- dihydrothiazol-4-yl-2,5-dihydrothiazol-5-yl, 2,3-dihydroimidazol-2-yl, 2,3-dihydro

-4-imidazolyl, 2,3-dihydro-5-imidazolyl, 4,5-dihydroimidazole

-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- and 3-morpholinyl, 2-, 3- and 4- piperidinyl,

3- and 4-tetrahydropyridazinyl, 2-, 4- and 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl, 1,3,5-tetrahydrotriazin-2-yl,

1,2,4-Tetrahydro-aziazione-3-yl, 1,3-dihydro-oxazin-2-yl, 1,3-dithian-2-yl, 2-tetrahydro-pyranyl, 1,3-dioxolan-2-yl- , 3,4,5,6-Tetrahydropindin-2-yl ·, 4H-1,3-thiazin-2-yl, 4H-3,1-benzothiazol-2-yl, 1,1-dioxo-2 , 3,4,5-Tetrahydrothien-2-yl, 2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazm-3-yl, 1,3-dihydrooxazin-2-yl -

1,3-dithiane-2-yl;

aryl, anyloxyl, arylthio, arylcarbonyl and arylsulfonyl groups: aromatic, mono- or polycyclic hydrocarbons which are directly on the (aryl) or oxygen (aryl-οχι) or sulfur (aryl) -thio) or a carbonyl group (arylcarbonyl) or a sulfonyl group (arylsulfonyl) attached to the parent compound such as phenyl, naphthyl, phenanthryl or phenoxy, naphthyloxy and phenanthryloxy and the corresponding thio- , carbonyl and sulfonyl groups;

arylamino group: an aromatic, mono- or polycyclic hydrocarbon group which is attached to the parent compound through a nitrogen atom;

heteroaryl, heteroaryloxy, heteroarylthio, heteroarylcarbonyl and heteroarylsulfonyl: an aromatic, mono- or polycyclic group containing from one to four nitrogen atoms or one to three nitrogen atoms and one or two sulfur atoms as heteroatoms may contain an oxygen or sulfur atom and may be ···· * directly (heteroaryl) or through an oxygen atom (heteroaryloxy) or a sulfur atom (heteroarylthio) or a carbonyl group (heteroarylcarbonyl) or a sulfonyl group (heteroarylsulfonyl) related to the parent compound, for example:

5-membered 5-membered heteroaryl containing one to three nitrogen atoms: 5-membered heteroaryl radicals containing one to three nitrogen atoms as ring members, such as 2- and 3-pyrrolyl, 3-, 4- and 5-pyrazolyl, 2- and 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 one oxygen or sulfur atom or one oxygen or sulfur atom: 5-membered heteroaryl groups having one to four nitrogen atoms or one to three nitrogen atoms and one sulfur as ring member or contain an oxygen atom or an oxygen or sulfur atom, for example 2 and 3-furyl, 2- and 3-thienyl, 2- and 3-pyrrolyl, 3-, 4- and 5-isoxazolyl, 3-, 4 - and 5-isothiazolyl, 3-, 4- and 5-pyrazolyl,

2-, 4- and 5-oxazolyl ·, 2-, 4- and 5-thiazolyl, 2- and 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 and 1,3,4-triazol-2-yl;

benzo-fused 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and / or an oxygen or sulfur atom: 5-membered heteroaryl groups having from one to four nitrogen atoms or one to 24 carbon atoms as ring members. containing a nitrogen atom and a sulfur or oxygen atom or an oxygen or sulfur atom and having two adjacent ring members which are carbon atoms or one of which is carbon and the other nitrogen atom is a butane-1,3-diene-1,4 -diyl group;

5-membered heteroaryl containing one to four nitrogen atoms attached through one of its nitrogen atoms or a benzo-fused five membered heteroaryl having one to three nitrogen atoms attached through one of its nitrogen atoms: 5 to 5 membered heteroaryl groups having one to four or one to three ring members containing a nitrogen atom and having two adjacent ring members which are carbon atoms or one of which is carbon and the other nitrogen atom can be linked by a buta-1,3-diene-1,4-diyl group and these rings are on one of their nitrogen atoms, as a ring member attached to the parent compound;

6-membered heteroaryl containing one to three or one to four nitrogen atoms: 6-membered heteroaryl having one to three and one to four nitrogen atoms as ring members, such as 2-, 3- and 4-pyridyl, 3- and 4-pyridazinyl, 2-, 4- and 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2 , 4,5-tetrazinyl;

benzocondensed 6-membered heteroaryl containing one to four nitrogen atoms: 6-membered heteroaryl groups in which two adjacent ring members which are carbon atoms can be linked by a buta-1,3-diene-1,4-diyl group; such heteroaromatic groups include, for example, quinolyl, isoquinolyl, quinazolinyl and quinoxalinyl, and the corresponding 0x1, thio, carbonyl or sulfonyl groups;

heteroarylamino group: aromatic, mono- or polycyclic groups containing, in addition to carbon atoms, one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or sulfur atom or one oxygen or sulfur atom attached as a ring member to the parent compound.

The term "partially or fully halogenated" means that the hydrogen atoms in the groups so characterized are replaced in whole or in part by the same or different halogen atoms, such as those mentioned above.

In terms of their biological activity, compounds of formula I wherein m = 0 are preferred.

The same effect, preferred are compounds of formula (I) in which ^R1 represents the methyl group atom.

Further preferred are compounds of formula I wherein R ³ is hydrogen, chlorine, hydroxy, cyclopropyl, methyl, ethyl, isopropyl, methoxy, methylthio or phenyl.

Further preferred are compounds of formula I wherein R is methyl.

Further preferred are compounds of formula I wherein R ^{3 is} methoxy.

• · · · · · · · · · · ·

Further preferred are compounds of formula I wherein R ^{3 is} hydroxy.

Further preferred are those compounds of formula I wherein R ^{3 is} chloro.

Further preferred are compounds of formula I wherein R is hydrogen, chlorine, hydroxy, cyclopropyl, methyl, ethyl, isopropyl, methoxy or methylthio.

Further preferred are compounds of formula I wherein R ^{4 is} methyl.

Further preferred are compounds of formula I wherein R is methoxy.

Further preferred are compounds of formula I wherein R ^{4 is} hydroxy.

Further preferred are compounds of formula I wherein R is ethyl.

Further preferred are compounds of formula I wherein R is isopropyl.

Further preferred are compounds of formula I wherein R is cyclopropyl.

Further preferred are compounds of formula I wherein R ^{4 is} aryl or heteroaryl.

Further preferred are compounds of formula I wherein R is phenyl.

Moreover, preferred are compounds of formula (I) in which R ⁵ represents methyl or ethyl wherein.

• ·

Further preferred are compounds of formula I wherein R? arylalkyl or heteroarylalkyl.

Further preferred are compounds of formula I wherein R ^{b is} aryloxyalkyl or heteroaryloxyalkyl.

Further preferred are compounds of formula I wherein R is optionally substituted aryl or heteroaryl.

Hereinafter, preferred are compounds of formula (I) wherein R ⁴ is optionally substituted pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl means.

Further preferred are compounds of formula I wherein R is optionally substituted furyl, thienyl or pyrrolyl.

Further preferred are those compounds of formula I wherein R is optionally substituted oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazolyl.

Further preferred are compounds of formula I wherein R is optionally substituted oxadiazolyl, thiadiazolyl or triazolyl.

Further preferred are compounds of formula I wherein R ^{4 is} a phenyl group which is not substituted or is substituted by one or two of the following groups: halogen, nitro, cyano, hydroxy, • amino, carbamoyl ·, thiocarbamoyl, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) -haloalkoxy, (C 1 -C 4) -alkyl-amino, C1-C4 dialkylamino, C1-C4 alkylsulfonyl, C1-C4 alkoxycarbonyl in the alkoxy moiety, C1-C4 alkylcarbamoyl in the alkyl moiety or C1-C4 dialkylcarbamoyl in the alkyl moiety.

Moreover preferred are compounds of formula (I) which is wherein R ⁵ is aryl or heteroaryl.

In particular, the compounds of formula I listed in the following tables are preferred.

Table 1

Compounds of formula (1.1) wherein

The combination of R, R and R substituents always represents 3 4 5 (R) _m hydrogen atoms corresponding to one of the rows in Table A.

Table 2

Compounds of formula (1.1) wherein R ( _m ) is chlorine and the combination of R, R and R always corresponds to one of the rows in Table A.

The table

Song R ³ R ⁴ R ⁵ 1 methyl methyl H 2 methyl methyl methyl 3 methyl methyl ethyl 4 methyl methyl propyl 5 methyl methyl isopropyl 6 methyl methyl cyclopropyl 7 methyl methyl butyl 8 methyl methyl z-butyl 9 methyl methyl isobutyl 10 methyl methyl tert-butyl 11 methyl methyl pentyl 12 methyl methyl isopentyl 13 methyl methyl neopentyl 14 methyl methyl cyclopentyl 15 methyl methyl hexyl 16 methyl methyl cyclohexyl 17 methyl methyl octyl 18 methyl methyl 2-chloroethyl 19 methyl methyl 4-chlorobutyl 20 methyl methyl cyanomethyl 21 methyl methyl 2-cyanoethyl 22 methyl methyl 3-cyanopropyl 23 methyl methyl 4-cyanobutyl 24 methyl methyl 6-cyano-hexyl

Song R ³ R ⁴ R ⁵ 25 methyl methyl cyclohexylmethyl 26 methyl methyl 2-cyclohexylethyl 27 methyl methyl cyclopropylmethyl 28 methyl methyl 2-cyclopropylethyl 29 methyl methyl 2-methoxyethyl 30 methyl mer 11 2-ethoxyethyl 31 methyl methyl 2-isopropoxy-ethyl 32 methyl methyl 3-methoxypropylamine 33 methyl methyl 3 is toxicopropyl 34 methyl methyl 3-isopropoxy-propyl 35 methyl methyl 4-methoxybutyl 3 β methyl met 11 4-isopropoxy-butyl 37 methyl methyl allyl 38 methyl methyl 2-butenyl 39 methyl methyl 3-butenyl meti1-2 40 methyl methyl 2- (vinyloxy) ethyl 41 methyl methyl allyl oxyethyl 42 methyl methyl 2- (trifluoromethoxy) ethyl 43 methyl methyl 3- (trifluoromethoxy) propyl 44 methyl Meril 4- (difluoromethoxy) butyl 45 methyl methyl carboxymethylcellulose 4 6 methyl methyl methoxycarbonyl-methyl 47 methyl methyl carbamoylmethyl 48 methyl methyl methyl-carbamoyl-methyl 49 methyl methyl dimetil-karbamoil-mer.il

• * · · «

Song R ³ R ⁴ - 5 n 50 methyl methyl 2-carboxyethyl Γ "Ί U ± methyl methyl 2- (methoxycarbonyl) ethyl 52 methyl methyl 2-carbamoyl-ethyl 53 methyl methyl 2- (methylcarbamoyl) ethyl 54 methyl methyl 2- (dimethylcarbamoyl) ethyl 55 me 111 methyl 2-aminoethyl 5 6 methyl methyl 2-propyl 57 methyl methyl 4-aminobutyl 58 methyl we til 3- (dimethylamino) propyl 59 methyl methyl 4-thiocarbamoyl-butyl 60 methyl methyl 2-oxo-propyl 61 methyl methyl cyclohexyl 62 methyl methyl cyclopropyl 63 methyl methyl cyclopentyl 64 methyl methyl 2- (methoxyimmo) -propyl 65 methyl methyl 2- (methoxyimino) ethyl 6 6 methyl methyl 6-carbamoyl-hexyl 67 methyl methyl 3-thiocarbamoyl-propyl 68 methyl methyl 2-thiocarbamoyl-ethyl 69 methyl methyl thiocarbamoyl methyl 70 methyl methyl 4- (dimethylamino) butyl 71 methyl methyl 2- (methylthio) ethyl 72 methyl methyl 2- (methylamino szalfonil) ethyl 73 methyl methyl 4- (methylthio) propyl 74 methyl methyl 4- (methylsulfonyl) propyl

• «

Song R ³ R ⁴ R ⁵ 75 methyl methyl benzi1 76 methyl methyl 2-fluorobenzyl 77 methyl methyl 3-fluorobenzyl 78 methyl methyl 4-fluorobenzyl 79 methyl methyl 2,3-difluorobenzyl · 80 methyl methyl 2,4-difluoro-benzyl 81 methyl methyl 2,5-difluoro-benzyl 82 methyl methyl 2,6-difluoro-benzyl 83 methyl we til 3,4-difluoro-benzyl 84 methyl methyl 3,5-difluoro-benzyl 85 methyl methyl 2-chlorobenzyl 86 methyl methyl 3-chlorobenzyl 87 methyl methyl 4-chlorobenzyl 88 methyl methyl 2,3-dichlorobenzyl 89 methyl methyl 2,4-dichlorobenzyl 90 methyl methyl 2,5-dichlorobenzyl 91 methyl methyl 2,6-dichlorobenzyl 92 methyl methyl 3,4-dichlorobenzyl 93 methyl methyl 3,5-dichlorobenzyl 94 methyl methyl 2,3,4-trichloro-benzyl 95 methyl methyl 2,3,5-trichloro-benzyl 96 methyl methyl 2,3,6-trichloro-benzyl 97 methyl methyl 2,4,5-trichloro-benzyl 98 methyl methyl 2,4,6-trichloro-benzyl 99 methyl methyl 3,4,5-trichloro-benzyl

Song 3 χΛ R ⁴ R ⁵ 100 methyl methyl 2-bromobenzyl 101 methyl methyl 3-bromobenzyl 102 methyl methyl 4-bromobenzyl 103 methyl me 111 2,3-dibromobenzyl 104 methyl methyl 2,4-dibromobenzyl 105 methyl methyl 2,5-dibromobenzyl 106 methyl methyl 2,6-dibromobenzyl 107 methyl methyl 3,4-dibromobenzyl 108 methyl methyl 3,5-dibromobenzyl 109 methyl methyl 2-fluoro-3-chlorobenzyl 110 methyl methyl 2-fluoro-4-chlorobenzyl 111 methyl methyl 2-fluoro-5-chlorobenzyl 112 methyl methyl 2-fluoro-3-bromobenzyl 113 methyl methyl 2-fluoro-4-bromobenzyl 114 methyl methyl 2-fluoro-5-bromobenzyl 115 methyl methyl 2-chloro-3-bromobenzyl 116 methyl methyl 2-chloro-4-bromo-benz11 117 methyl mer 11 2-chloro-5-bromobenzyl 118 methyl methyl 3-Fluoro-4-chlorobenzyl 119 methyl me o i 1 3-fluoro-5-chlorobenzyl 120 methyl methyl 3-fluoro-6-chlorobenzyl 121 methyl methyl 3-fluoro-4-bromobenzyl 122 methyl methyl 3-fluoro-5-bromobenzyl 123 methyl meoil 3-fluoro-6-bromo-benzyl 124 methyl meoil 3-chloro-4-bromobenzyl

Song R ³ R ⁴ R ⁵ 125 methyl methyl 3-chloro-5-bromobenzyl 126 methyl methyl 3-chloro-6-bromobenzyl 127 methyl methyl 4-fluoro-5-chlorobenzyl 128 methyl methyl 4-fluoro-6-chlorobenzyl 129 methyl methyl 4-fluoro-5-bromobenzyl 130 methyl methyl 4-Fluoro-6-bromobenzyl 131 methyl methyl 4-chloro-5-bromobenzyl 132 methyl methyl 5-fluoro-6-chlorobenzyl 133 methyl methyl 5-fluoro-6-bromobenzyl 134 methyl methyl 5-chloro-6-bromo-benz11 135 methyl methyl 3,5-dibromo-4-chlorobenzyl 136 methyl methyl 2-cyanobenzyl 137 methyl methyl 3-cyano-benzyl 138 methyl methyl 4-cyano-benzyl 139 methyl methyl 2-Nitrobenzyl 140 methyl methyl 3-nitrobenzyl 141 methyl methyl 4-nitrobenzyl 142 methyl methyl 2-methylbenzyl 143 methyl methyl 3-methylbenzyl 144 methyl methyl 4-methylbenzyl 145 methyl methyl 2,3-dimethylbenzyl 146 methyl methyl 2,4-dimethylbenzyl 147 methyl methyl 2,5-dimethylbenzyl 148 methyl methyl 2,6-dimethylbenzyl 149 methyl methyl 3,4-dimethylbenzyl

• · · · «

Song 9 R7 R ⁴ R 150 methyl methyl 3,5-dimethylbenzyl 151 methyl methyl 2-ethylbenzyl 152 methyl Ii tii 3-ethylbenzyl 153 methyl methyl 4-ethyl-benzyl 154 methyl we til 2-isopropylbenzyl 155 methyl methyl 3-benzyl-izopropi1 156 me 111 methyl 4-Isopropyl-benzyl 157 methyl methyl 2-cyclohexyl-benzyl 158 methyl methyl 3-Cyclohexyl-benzyl 159 methyl methyl 4-cyclohexyl-benzyl 160 methyl methyl 2-vinylbenzyl 161 methyl methyl· 3-benzyl-vmil 162 methyl methyl 4-vinylbenzyl 163 methyl methyl 2-allyl-benzyl 164 methyl methyl 3-allyl-benzyl 165 methyl methyl 4-benzyl-alli1 166 methyl methyl 2-phenylbenzyl 167 methyl methyl 3-phenylbenzyl 168 methyl methyl 4-phenylbenzyl 169 methyl methyl 3-methyl-5-tert-butylbenzyl 170 methyl methyl 2-hydroxy-benzí1 171 methyl methyl 3-hydroxybenzyl 172 methyl methyl 4-hydroxybenzyl 173 methyl methyl 2-methoxybenzyl 174 methyl methyl 3-methoxybenzyl

• ·

6

Song R ³ R ⁴ R ⁵ 175 met 11 methyl 4-methoxybenzyl 17 6 methyl methyl 2,3-dimethoxybenzyl 177 methyl methyl 2,4-dimethoxybenzyl 178 methyl methyl 2,5-dimethoxy-benzyl 179 methyl methyl 3,4-dimethoxybenzyl 180 methyl methyl 3,5-dimethoxy-benzyl 181 methyl methyl 3,4,5-trimethoxybenzyl 182 methyl methyl 2-ethoxy-benzyl 183 methyl methyl 3-ethoxybenzyl 184 methyl methyl 4-ethoxy-benzyl 185 methyl methyl 2-propoxy-benzyl 186 methyl methyl 3-propoxy-benzyl 187 methyl methyl 4-propoxy-benzyl 188 methyl methyl 2-isopropoxy-benzyl 189 methyl methyl 3-Isopropoxybenzyl 190 methyl methyl 4-isopropoxy-benzyl 191 methyl methyl 4-Butoxy-benzyl 192 methyl methyl 3-tert-butoxy-benzyl 193 methyl me t i 1 4- (hexyloxy) benzyl 194 methyl methyl 2- (allyloxy) benzyl 195 methyl methyl 3- (Allyloxy) benzyl 196 methyl methyl 4- (allyloxy) benzyl 197 methyl methyl 2-CF ₃ benzyl 198 methyl methyl 3-CF ₃ benzyl 199 methyl methyl 4-CF ₃ benzyl

Song R R ⁴ R ⁵ 200 methyl methyl 2-acetyl-benzyl 201 methyl methyl 3-acetyl-benzyl 202 methyl methyl 4-acetyl-benzyl 203 methyl me 111 2- (methoxycarbonyl) benzyl 204 methyl methyl 3- (methoxycarbonyl) benzyl 205 methyl sea 1 4- (methoxycarbonyl) benzyl 206 methyl methyl 2-carbamoyl-benzyl 207 methyl methyl 3-carbamoyl-benzyl 208 methyl methyl 4-carbamoyl-benzyl 209 methyl methyl 2- (dimethylamino) benzyl 210 methyl methyl 3- (dimethylcarbamoyl) -benzyl 211 methyl methyl 4- (dimethylamino) benzyl 212 methyl methyl 2- (methylcarbamoyl) -benzyl 213 methyl methyl 3- (methylcarbamoyl) -benzyl 214 me t i 1 methyl 4- (methylcarbamoyl) benzyl 215 methyl methyl 2-aminobenzyl 216 methyl methyl 3-aminobenzyl 217 methyl methyl 4-aminobenzyl 218 methyl methyl 2-thiocarbamoyl-benzyl 219 methyl me t i 1 3-thiocarbamoyl-benzyl 220 methyl methyl 4-thiocarbamoyl-benzyl 221 methyl methyl 2- (methoxyimino-methyl) benzyl 222 methyl methyl 3- (methoxyimino-methyl) benzyl 223 methyl methyl 4- (methoxyimino-methyl) benzyl 224 methyl methyl 2-formyl-benzyl

• ·

Song 5 Irish R ⁴ R ⁵ 225 methyl methyl 3-formylbenzyl 226 methyl methyl 4-formyl-benzyl 227 methyl methyl 2- (1-methoxyimino-ethyl) -benzyl 228 methyl methyl 3- (1-methoxyiminoethyl) benzyl 229 methyl methyl 4- (1-methoxyimino-ethyl) -benzyl 230 methyl methyl 2- (methylthio) benzyl 231 we til methyl 3- (methylthio) benzyl 232 methyl methyl 4- (methylthio) benzyl 233 methyl me 111 2- (methylsulfonyl) benzyl 234 methyl methyl 3- (methylsulfonyl) benzyl 235 methyl methyl 4- (methylsulfonyl) benzyl 236 methyl methyl 2- (trifluoromethoxy) benzyl 237 methyl methyl 3- (trifluoromethoxy) benzyl 238 methyl methyl 4- (orifluor-ylmethoxy) benzyl 239 methyl methyl 2- (difluoromethoxy) benzyl 240 methyl methyl 3- (difluoromethoxy) benzyl 241 methyl methyl 4- (difluoromethoxy) benzyl 242 methyl methyl 3- (trifluoromethyl) -4- - (trifluoro-methoxy) benzyl 243 methyl methyl 1-naphthylmethyl 244 methyl methyl 2-naphthyl met11 245 methyl methyl 2-phenoxyethyl 246 methyl methyl 2- (2-chlorophenoxy) ethyl 247 methyl methyl 2- (3-chlorophenoxy) ethyl 248 methyl methyl 2- (4-chlorophenoxy) ethyl

• ·

Song R ³ R ⁴ R ⁵ 249 methyl methyl 2- (3,5-dichlorophenoxy) ethyl 250 methyl methyl 2- (2-cyanophenoxy) ethyl 251 methyl· methyl 2- (3-cyanophenoxy) ethyl 252 methyl methyl 2- (4-cyanophenoxy) ethyl 253 methyl methyl 2- (2-methylphenoxy) ethyl 254 methyl methyl 2- (3-methylphenoxy) ethyl 255 methyl methyl 2- (4-methylphenoxy) ethyl 256 methyl methyl 2- (3-tert-Butyl-phenoxy) -ethyl 257 methyl we til 2- (4-tert-butyl-phenoxy) -ethyl 258 methyl methyl 2- (2-nitrophenoxy) ethyl 259 methyl methyl 2- (3-nitrophenoxy) ethyl 260 methyl methyl 2- (4-nitrophenoxy) ethyl 2 61 methyl methyl 2- (2-methoxyphenoxy) ethyl 2 62 methyl methyl 2- (3-methoxyphenoxy) ethyl 263 methyl methyl 2- (4-methoxyphenoxy) ethyl 264 methyl methyl 2- (2-CF ₃ -phenoxy) ethyl 265 methyl methyl 2- (3-CF ₃ -phenoxy) ethyl 266 methyl methyl 2- (4-CF ₃ -phenoxy) ethyl 267 methyl methyl 2- (2-acetyl-phenoxy) -ethyl 268 methyl methyl 2- (3-acetyl-phenoxy) -ethyl 269 methyl methyl 2- (4-Acetyl-phenoxy) -ethyl 270 methyl methyl 2- (2-CH ₃ O-CO-phenoxy) ethyl 271 methyl methyl 2- (3-CH ₃ O-CO-phenoxy) -ethyl 272 methyl methyl 2- (4-CH ₃ O-CO-phenoxy) ethyl 273 methyl methyl 2- (2- (CH ₃ ) ₂ N-CO-phenoxy) ethyl

Song R ³ R ⁴ R ⁵ 27 4 methyl methyl 2- (3- (CH ₃ ) ₂ N-CO-phenoxy) ethyl 275 methyl methyl 2- (4- (CH ₃ ) ₂ N-CO-phenoxy) ethyl 276 methyl mer ii 2- (2-thiocarbamoyl-phenoxy) -ethyl 277 methyl we ni 2- (3-Thiocarbamoyl-phenoxy) -ethyl 278 methyl methyl· 2- (4-Thiocarbamoyl-phenoxy) -ethyl 279 methyl mesylate 2- (2-CH ₃ SO ₂ -phenoxy) ethyl 280 methyl methyl 2- (3-CH ₃ SO ₂ -phenoxy) ethyl 281 methyl methyl 2- (4-CH ₃ SO ₂ -phenoxy) ethyl 282 methyl we lil 3-phenoxypropyl 283 me t i i me 111 3- (2-chlorophenoxy) propyl 284 methyl methyl· 3- (3-chlorophenoxy) propyl 285 methyl methyl 3- (4-chlorophenoxy) propyl 2 8 6 methyl methyl 3- (3,5-dichlorophenoxy) propyl 287 methyl methyl 3- (2-cyanophenoxy) propyl 288 methyl methyl 3- (3-cyanophenoxy) propyl 289 methyl methyl 3- (4-cyanophenoxy) propyl 290 methyl methyl 3- (2-methylphenoxy) propyl 291 methyl me i i 1 3- (3-methylphenoxy) propyl 292 methyl mesylate 3- (4-methylphenoxy) propyl 293 methyl mesylate 3- (2-methoxyphenoxy) propyl 294 methyl jersey 3- (3-methoxyphenoxy) propyl 295 methyl mesylate 3- (4-methoxyphenoxy) propyl 296 methyl jersey 3- (2-CF ₃ -phenoxy) -propyl 297 methyl mesylate 3- (3-CF ₃ -phenoxy) -propyl 298 methyl mesylate 3- (4-CF ₃ -phenoxy) -propyl

• · · · ·

Song R ³ R ⁴ T-5 299 methyl methyl 4-phenoxy-butyl 300 mer il methyl phenethyl 301 mer il methyl 2- (2-chlorophenyl) ethyl 302 methyl me 111 2- (3-chlorophenyl) ethyl 303 methyl methyl 2- (4-chlorophenyl) ethyl 304 methyl methyl 2- (3,5-dichlorophenyl) -eril 305 methyl me r i 1 2- (2-cyanophenyl) ethyl 306 methyl methyl 2- (3-cyanophenyl) ethyl 307 methyl methyl 2- (4-cyanophenyl) ethyl 308 methyl methyl 2- (2-methylphenyl) ethyl 309 methyl methyl 2- (3-methylphenyl) ethyl 310 methyl methyl 2- (4-methylphenyl) ethyl 311 methyl methyl 2- (2-methoxyphenyl) ethyl 312 methyl methyl 2- (3-methoxyphenyl) ethyl 313 methyl methyl 2- (4-methoxyphenyl) ethyl 314 methyl methyl 2- (2-CF ₃ -phenyl) ethyl 315 methyl methyl 2- (3-CF ₃ -phenyl) ethyl 316 methyl methyl 2- (4-CF ₃ -phenyl) ethyl 317 methyl Meril 3-phenylpropyl 318 methyl methyl 3- (2-chlorophenyl) -propyl 319 methyl Meril 3- (3-chlorophenyl) propyl 320 methyl methyl 3- (4-chlorophenyl) propyl 321 methyl methyl 3- (2-cyanophenyl) propyl 322 methyl Meril 3- (3-cyanophenyl) propyl 323 methyl methyl 3- (4-cyanophenyl) propyl

• «

Song R ^J R ⁴ R ⁵ 324 methyl methyl 3- (2-CF ₃ -phenyl) -propyl 325 methyl methyl 4-phenylbutyl 326 methyl we til 4- (4-chlorophenyl) butyl 327 methyl methyl 6- (4-chlorophenyl) hexyl 328 methyl methyl 2-pyridylmethyl 329 methyl methyl 3-pyridylmethyl 330 methyl methyl 4-pyridylmethyl 331 methyl methyl 4-chloro-2-pyridylmethyl 332 methyl methyl 5-chloro-2-pyridylmethyl 333 methyl methyl 6-chloro-2-pyridylmethyl 334 methyl methyl 5-chloro-3-pyridylmethyl 335 methyl methyl 6-chloro-3-pyridylmethyl 336 methyl methyl 2-chloro-4-pyridyl-methyl 337 methyl methyl 2-pyrimidinylmethyl 338 methyl methyl 4-chloro-2-methyl-pyrimidinyl 339 methyl methyl 5-chloro-2-methyl-pyrimidinyl 340 methyl methyl 2-chloro-4-pyrimidinylmethyl 341 methyl methyl 6-chloro-4-pyrimidinylmethyl 342 methyl methyl 2-chloro-5-pyrimidinylmethyl 343 methyl methyl 4-Pyridazinylmethyl 344 methyl methyl 2-pyrazinylmethyl 345 methyl methyl 5-chloro-2-pyrazinylmethyl 346 methyl methyl 6-chloro-2-pyrazinylmethyl 347 methyl methyl Methyl-3-pyridazinyl 348 methyl methyl 6-chloro-3-pyridazinylmethyl

··

Song R ³ R ⁴ R ⁵ 349 methyl methyl 1,3,5-methyl-trrazinil 350 methyl methyl 2-furylmethyl 351 methyl methyl 3-furyl-meter 352 methyl methyl 4-bromo-2-methyl-fúri1 353 methyl methyl 5-chloro-2-furylmethyl 354 methyl methyl 2-thienylmethyl 355 methyl methyl 3-thienylmethyl 356 methyl methyl 5 meti1-3-thienylmethyl 357 methyl methyl 5-chloro-2-thienylmethyl 358 methyl methyl 2-chloro-4-thienylmethyl 359 methyl methyl 2-pyrrolylmethyl 360 methyl methyl 3-pyrrolylmethyl 361 methyl methyl 2-oxazolylmethyl 362 methyl methyl 4-methyl-2-oxazolyl-methyl 363 methyl methyl 5-methyl-2-oxazolyl-methyl 364 methyl methyl 4-chloro-2-methyl-oxazole 365 methyl methyl 5-chloro-2-methyl-oxazole 366 methyl methyl 4-oxazolylmethyl 367 methyl methyl 2-methyl-4-oxazolylmethyl 368 methyl methyl 5-methyl-4-oxazolylmethyl 369 methyl methyl 2-chloro-4-oxazolylmethyl 370 methyl methyl 5-chloro-4-oxazolylmethyl 371 methyl methyl 5-oxazolylmethyl 372 methyl methyl 2-methyl-5-oxazolylmethyl 373 methyl methyl 4-methyl-5-oxazolylmethyl

Song R ³ R ⁴ R ⁵ 374 methyl methyl 2-chloro-5-methyl-oxazole 375 methyl methyl 4-chloro-5-methyl-oxazole 376 methyl methyl 2-thiazolylmethyl 377 methyl methyl 4-methyl-2-thiazolylmethyl 378 methyl methyl 5-methyl-2-thiazolylmethyl 379 methyl me 111 4-chloro-2-thiazolylmethyl 380 methyl methyl 5-chloro-2-thiazolylmethyl 381 methyl methyl 4-thiazolylmethyl 382 methyl methyl 2-methyl-4-thiazolylmethyl 383 methyl methyl Met11-4-5-thiazolylmethyl 384 methyl methyl 2-chloro-4-thiazolylmethyl 385 methyl methyl 5-chloro-4-thiazolylmethyl 386 methyl methyl 5-thiazolylmethyl 387 methyl methyl 2-methyl-5-thiazolylmethyl 388 methyl methyl 4-methyl-5-thiazolylmethyl 389 methyl methyl 2-chloro-5-thiazolylmethyl 390 methyl methyl 4-chloro-5-thiazolylmethyl 391 methyl methyl Methyl-3-isoxazolyl 392 methyl methyl 4-methyl-3-isoxazolyl-methyl 393 methyl methyl 5-methyl-3-ioxoxazolylmethyl 394 methyl methyl 4-chloro-3-methyl-isoxazolyl 395 methyl methyl 5-chloro-3-methyl-isoxazolyl 396 methyl methyl 4-methyl-isoxazolyl 397 methyl methyl 3-methyl-4-isoxazolylmethyl 398 methyl methyl 5-methyl-4-isoxazolyl-methyl

Song R ³ D ⁴ R R 399 methyl me 11 i 3-chloro-4-methyl-isoxazolyl 400 methyl methyl 5-chloro-4-methyl-isoxazolyl 401 methyl· methyl· Methyl-5-isoxazolyl 402 methyl methyl 3-methyl-5-isoxazolyl-methyl 403 methyl methyl 4-methyl-5-ioxoxazolylmethyl 404 methyl methyl 3-chloro-5-methyl-isoxazolyl 405 methyl methyl 4-methyl-5-isoxazolyl 406 methyl methyl 3-methyl-isothiazolyl 407 methyl methyl 4-methyl-3-methyl-isothiazolyl 403 methyl methyl 5-methyl-3-methyl-isothiazolyl 409 methyl methyl 4-chloro-3-methyl-isothiazolyl 410 methyl methyl 5-chloro-3-methyl-isothiazolyl 411 methyl methyl Isothiazol-4-methyl- 412 methyl methyl 3-methyl-4-methyl-izotiazoiil 413 methyl methyl 5-methyl-isothiazol-4-methyl- 414 methyl methyl 3-chloro-4-methyl-isothiazolyl 415 methyl methyl 5-chloro-4-methyl-izotiazoiil 416 methyl methyl 5-isothiazolylmethyl 417 methyl methyl 3-methyl-5-methyl-izotiazoiil 418 methyl methyl 4-methyl-5-methyl-izotiazoiil 419 methyl methyl 3-chloro-5-methyl-isothiazolyl 420 methyl methyl 4-chloro-5-methyl-izotiazoiil 421 methyl methyl 4-imidazolylmethyl 422 methyl methyl 1-phenyl-3-pyrazolyl methyl 423 methyl methyl 1-methyl-4-imidazolylmethyl

· · · · · · · · ·

Song R ³ R ⁴ c R 424 methyl methyl l-phenyl-l, 2,4-triazol-3-yl -methyl 425 methyl methyl 1,2,4-oxadiazol-3-ylmethyl 426 methyl methyl 5-chloro-l, 2,4-oxadiazol-3-yl -methyl 427 methyl methyl Meti1-1,2,4 5-oxadiazol-3-yl -methyl 428 methyl methyl 5- (trifluoromethyl) -1,2,4- oxadiazol-3-ylmethyl 42 9 methyl methyl 1,3,4-oxadiazol-2-ylmethyl 430 methyl methyl 5-chloro-l, 3,4-oxadiazol-2-yl -methyl 431 methyl methyl 5-methyl-i, 3,4-oxadiazol-2-yl methyl 432 methyl methyl 5-methoxy-l, 3,4-oxadiazol-2-yl -methyl 433 methyl methyl 1,2,4-thiadiazol-3-ylmethyl 434 methyl methyl 5-chloro-l, 2,4-thiadiazol-3-yl -methyl 435 methyl methyl 5-methyl-l, 2,4-thiadiazol-3-yl -methyl 436 methyl methyl 1,3,4-thiadiazol-2-yl-methyl 437 methyl methyl 5-chloro-l, 3,4-thiadiazol-2-yl -methyl 438 methyl methyl 5-methyl-l, 3,4-thiadiazol-2-yl

• · · · ·

Song R ³ R ⁴ ζ R ^J -methyl 439 methyl methyl 5-cyano-l, 3,4-thiadiazol-2-yl -methyl 440 jersey 11 methyl 2- (2-pyridyloxy) ethyl 441 methyl methyl 2- (3-pyridyloxy) ethyl 442 methyl methyl 2- (4-pyridyloxy) ethyl 443 methyl methyl 2- (2-pyrimidinyloxy) ethyl 444 methyl methyl 2- (4-pyrimidinyloxy) ethyl 445 methyl methyl 2- (5-pyrimidinyloxy) ethyl 446 methyl methyl 2- (2-pyrazinyloxy) ethyl 447 methyl methyl 2- (2-pyridazinyloxy) ethyl 448 methyl methyl 2- (3-pyridazinyloxy) ethyl 449 methyl methyl 2- (1,3,5-triazinyloxy) ethyl 450 methyl methyl 2- (5-methyl-furan-3-isoxazolyl) - -ethyl 451 methyl methyl 2- (5-chloro-3-isoxazolyloxy) - -ethyl 452 methyl methyl 2- (2-methoxy-4-thiazolyl) - -ethyl 453 methyl methyl 2- (4-chloro-2-oxazolyl) -ethyl 454 methyl methyl 2- (1-phenyl-1H-1,2,4-triazole-3- yloxy) ethyl 455 methyl methyl 2- (l-phenyl-3-pyrazolyl) - -ethyl 456 methyl methyl phenyl

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Song R ³ R ⁴ R ⁵ 457 methyl methyl 2-chlorophenyl 458 methyl methyl 3-chlorophenyl 459 methyl methyl 4-chlorophenyl 460 methyl methyl 2,3-dichlorophenyl 461 methyl methyl 2,4-dichlorophenyl 462 methyl methyl 2,5-dichlorophenyl 463 methyl mer il 3,4-dichlorophenyl 4 64 methyl methyl 3,5-dichlorophenyl 465 methyl methyl 4-cyanophenyl 466 methyl methyl 2-nitrophenyl 467 methyl methyl 3-nitrophenyl 468 methyl methyl 4-nitrophenyl 4 69 methyl methyl 2,4-dinitrophenyl 470 methyl dare! 2-methylphenyl 471 methyl methyl 3-methylphenyl 472 methyl methyl 4-methylphenyl 473 methyl Meril 2,3-dimethylphenyl 474 methyl methyl 2,4-dimethylphenyl 475 methyl Meril 2,5-dimethylphenyl 476 methyl Meril 2,6-dimethylphenyl 477 methyl Meril 2-biphenylyl 478 methyl Meril 3-biphenylyl 479 methyl Meril 4-biphenylyl 480 methyl Meril 3-methoxyphenyl 481 methyl Meril 4-methoxyphenyl

Song R R ⁴ R ⁵ 482 methyl methyl 3-acetylphenyl 483 methyl methyl 4-acetylphenyl 484 methyl methyl 3- (methoxycarbonyl) phenyl 485 methyl methyl 4- (methoxycarbonyl) phenyl 486 methyl methyl 3- (trifluoromethyl) phenyl 487 methyl methyl 4- (trifluoromethyl) phenyl 488 methyl Meril 2-naphthyl 489 methyl breast 1 6-chloro-3-pyridazinyl 490 methyl methyl 5-chloro-2-pyrazinyl 491 methyl methyl 2-quinolinyl 4 92 methyl methyl 2,5-dimethyl-3-pyrazinyl 493 methyl Meril 2-pyrazinyl 494 methyl methyl 3-chloro-2-pyridyl 495 mer il methyl 6- <chloropyridine-2-pyridyl 496 methyl mer.il 4-CF ₃ -6-chloro-2-pyridyl 497 methyl sea 1 4- (trifluoromethyl) -2-pyridyl 498 methyl dare! 6- (trifluoromethyl) -2-pyridyl 499 methyl methyl 6-methoxy-2-pyridyl 500 methyl methyl 5-chloro-2-pyridyl 501 methyl methyl 2-pyridyl 502 methyl methyl benzothiazol-2-yl 503 methyl methyl 7-Chloro-4-quinolinyl 504 methyl methyl 3-nitro-2-pyridyl 505 methyl methyl 3-pyrroline 506 methyl methyl 2-pyrrolyl

Song • 3 tr R ⁴ R ⁵ 507 methyl methyl 2,6-dioctyl-4-pyridyl 508 methyl methyl 5-nitro-2-pyridyl 50 9 methyl methyl 4-pyridyl 510 methyl methyl 3-pyridyl 511 methyl methyl 2-pyrimidinyl 512 methyl methyl 4-pyrimidinyl 513 methyl methyl 4-quinazolinyl 514 methyl methyl 6-chloro-4-pyrimidinyl 515 methyl methyl 6-methoxy-4-pyrimidinyl 516 methyl methyl 2,5,5-trichloro-4-pinnimidinyl 517 methyl methyl 2,6-dimethyl-4-pyrimidinyl 518 methyl methyl 2-methyl-6-chloro-4-pyrimidinyl 519 methyl methyl 2-methyl-6-ethoxy-4-pyrimidinyl 520 methyl methyl 4,5,6-trichloro-2-pyrimidinyl 521 methyl methyl 4,6-dimethoxy-2-pyrimidinyl 522 methyl methyl 4,6-dimethyl-2-pyrimidinyl 523 methyl methyl 4,6-dichloro-2-pyrimidinyl 524 methyl methyl 4-methyl-6-methoxy-2-pyrimidinyl 525 methyl methyl 4-chloro-6-methoxy-2-pyrimidinyl 526 methyl methyl 6-chloro-2-quinoxalinyl 527 methyl methyl 3,6-dichloro-l, 2,4-triazin-5-yl 528 methyl methyl 4-methoxy-l, 3,5-triazin-2-yl 529 methyl methyl 4-ethoxy-l, 3,5-triazin-2-yl 530 methyl methyl 4,6-dichloro-l, 3,5-triazin-2-yl 531 methyl methyl 4-ethoxy-6-chloro-l, 3,5-triazine

Song R ³ R ⁴ R ⁵ -2-yl 532 methyl methyl 3-isoxazolyl 533 methyl methyl 2-thienyl 534 methyl methyl 2-furyl 535 methyl methyl tiatriazcl-5-yl 536 methyl methyl (E) -3-propylphenyl propenyl 537 methyl methyl (E) -4- (p-chlorophenyl) -2-butenyl 538 methyl methyl propynyl 539 methyl methyl Methylaminocarbonyl 540 methyl methyl ethylcarbonyl 541 methyl methyl Carbonyl propi1 542 methyl methyl Isopropylamino-carbonyl 543 methyl methyl -Butylcarbonyl 544 methyl methyl Carbonyl-sec-butyl 545 methyl methyl Benzyloxycarbonyl 546 methyl methyl Carbonyl-tert-butyl 547 methyl methyl Carbonyl pentyl 548 methyl methyl Carbonyl isopentyl 549 methyl methyl -Neopentyloxycarbonyl 550 methyl methyl Carbonyl-hexyl 551 methyl methyl Carbonyl-octyl 552 methyl methyl Carbonyl-1-propenyl 553 methyl methyl Carbonyl-2-pentenyl 554 methyl methyl Carbonyl-hepta-2,5-dienyl 555 methyl methyl benzoyl

Song R ³ R ⁴ R ⁵ 556 ΓΠΘ Very methyl 2-chlorobenzoyl 557 methyl methyl 3-chlorobenzoyl 558 methyl methyl 4-chloro-benzol1 559 methyl methyl 2-cyano-benzol1 560 methyl methyl 3-cyanobenzoyl 561 methyl methyl 4-cyanobenzoyl 562 methyl methyl 4-methoxybenzoyl 563 methyl methyl Carbonyl-2-pyridyl 564 methyl methyl -3-pyridylcarbonyl 565 methyl methyl N-4-pyridyl 566 methyl methyl Carbonyl-2-pyrimidinyl 567 methyl methyl Carbonyl-2-oxazolyl 568 methyl methyl Carbonyl-4-methyl-5-isoxazolyl 569 methyl methyl methylsulfonyl 570 methyl methyl ethylsulfonyl 571 methyl methyl propylsulfonyl 572 methyl methyl isopropylsulfonyl 573 methyl methyl butylsulfonyl 574 methyl methyl terbutylsulfonyl 575 methyl methyl pentylsulfonyl 576 methyl methyl neopentyl sulfonyl 577 methyl methyl hexylsulfonyl 578 methyl methyl octyl-sulfonyl 579 methyl methyl phenylsulfonyl 580 methyl methyl 2-chloro-phenylsulfonyl

Song R ³ R ⁴ R ⁵ 581 methyl methyl 3-chloro-phenylsulfonyl 582 methyl methyl 4-chlorophenyl-sulfonyl 583 methyl methyl 2-cyano-phenylsulfonyl 584 methyl methyl 3-cyano-phenylsulfonyl 585 methyl methyl 4-cyanophenyl-sulphonyl 586 methyl Meril 2-pyridyl-sulfonyl 587 methyl methyl 3-pyridylsulfonyl 588 methyl methyl 4-pyridylsulfonyl 589 methyl methyl 2-pyrimidinylsulfonyl 590 methyl methyl 4-oxazolyl sulfonyl 591 methyl methyl 5-chloro-2-thiazolylsulfonyl 592 methyl methyl 2-t-butyl benzyl 593 methyl methyl 3-tert-butyl-benzyl 594 methyl methyl 4-tert-butylbenzyl 595 methyl methyl 2- (4-chloro-2-thiazolyloxy) ethyl 596 methyl methyl 2- (1-methyl-4-pyrazolyloxy) - -ethyl 597 methyl methyl 4-bromophenyl 598 methyl methyl 3,5-dimethylphenyl 599 methyl methyl 4-ethylphenyl 600 methyl methyl 3- (dimethylcarbamoyl) phenyl 601 methyl methyl 4- (dimethylcarbamoyl) phenyl 602 methyl methyl 2-hydroxypropyl 603 methyl methyl 6-hydroxy-2-methyl-pyrimidin-4- -ylmethyl

Song _ 3 K R ⁴ R ⁵ 604 methyl methyl 6-hydroxy-2-isopropyl-4- pyrimidinyl methyl 605 methyl methyl 6-hydroxy-2-izoprop11-4- pyrimidinyl methyl 606 methyl methyl 5- (2-furyl) -pentyl 607 methyl methyl 5- (N-methyl-2-pyrrolyl) pentyl 608 methyl methyl 2- (p-chlorophenyl) -4-oxazolyl -raet11 609 methyl methyl 3- (trifluoromethyl) -2-pyridyl 610 methyl methyl 5- (trifluoromethyl) -2-pyridyl 611 methyl methyl 6- (2-thienyl) hexyl 612 methyl tert-butyl H 613 methyl tert-butyl methyl 614 methyl tert-butyl ethyl 615 methyl tert-butyl propyl 616 methyl tert-butyl isopropyl 617 methyl tert-butyl cyclopropyl 618 methyl tert-butyl butyl 619 methyl tert-butyl tert-butyl 620 methyl tert-butyl hexyl 621 methyl tert-butyl (E) -3-chloro-propenyl 622 methyl tert-butyl propynyl 623 methyl tert-butyl 3-butenyl met11-2 624 methyl tert-butyl 2-naphthylmethyl 625 methyl tert-butyl 4-chlorobenzyl

«·

Song R ³ R ⁴ R ⁵ 626 methyl tert-butyl (E) -4- (p-chlorophenyl) -2-butenyl 627 methyl tert-butyl 6- (p-chlorophenyl) hexyl 628 methyl tert-butyl 3- (trifluoromethyl) phenyl 629 methyl phenyl H 630 methyl phenyl methyl 631 methyl phenyl ethyl 632 methyl phenyl propyl 633 methyl phenyl isopropyl 634 methyl phenyl cyclopropyl 635 methyl phenyl butyl 636 methyl phenyl tert-butyl 637 methyl phenyl hexyl 638 methyl phenyl 4-chlorobenzyl 639 methyl phenyl 3- (trifluoromethyl) phenyl 640 methyl phenyl 6- (p-chlorophenyl) hexyl 641 methyl phenyl (E) -4- (p-chlorophenyl) -2-butenyl 642 methyl H H 643 methyl H methyl 644 methyl H ethyl 645 methyl H propyl 64 6 methyl H isopropyl 647 methyl OH H 648 methyl OH methyl 649 methyl OH ethyl 650 methyl OH propyl

Song R ³ R ⁴ R ⁵ 651 methyl OH isopropyl 652 methyl chlorine methyl 653 methyl chlorine ethyl 654 methyl gets out propyl 655 methyl chlorine isopropyl 656 methyl methoxy H 657 methyl methoxy methyl 658 methyl methoxy ethyl 659 methyl methoxy propyl 660 methyl methoxy isopropyl 661 methyl methylthio H 662 methyl methylthio methyl 663 methyl methylthio ethyl 664 methyl methylthio propyl 665 methyl methylthio isopropyl 666 methyl cyclopropyl H 667 methyl cyclopropyl methyl 668 methyl cyclopropyl ethyl 669 methyl cyclopropyl propyl 670 methyl cyclopropyl isopropyl 671 methyl 2-pyridyl H 672 methyl 2-pyridyl methyl 673 methyl 2-pyridyl ethyl 674 methyl 2-pyridyl propyl 675 methyl 2-pyridyl isopropyl

• ·

5Ί

Song R ³ R ⁴ R ' 676 methyl 3-pyridyl H 677 methyl 3-pyridyl methyl 678 methyl 3-pyridyl ethyl 679 methyl 3-pyridyl propyl 680 methyl 3-pyridyl isopropyl 681 we til 4-pyridyl H 682 methyl 4 piridi1 methyl 683 methyl 4-pyridyl ethyl 684 methyl 4-pyridyl propyl 685 methyl 4-pyridyl isopropyl 686 methyl 2-pyrimidinylamino H 687 methyl 2-pyrimidinyl methyl 688 methyl 2-pyrimidinyl ethyl 689 methyl 2-pyrimidinyl propyl 690 methyl 2-pyrimidinyl isopropyl 691 methyl 4-pyrimidinyl H 692 methyl 4-pyrimidinyl methyl 693 methyl 4-pyrimidinyl ethyl 694 methyl 4-pyrimidinyl propyl 695 methyl 4-pyrimidinyl isopropyl 696 methyl 5-pyrimidinyl H 697 methyl 5-pyrimidinyl methyl 698 methyl 5-pyrimidinyl ethyl 699 methyl 5-pyrimidinyl propyl 700 methyl 5-pyrimidinyl isopropyl

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Song R ³ R ⁴ R ⁵ 701 methyl 1,3,5-tnazínil H 702 methyl 1,3,5-triazinyl methyl 703 methyl· 1,3,5-triazinyl ethyl 704 methyl· 1,3,5-triazinyl propyl 705 methyl 1,3,5-triazinyl isopropyl 706 methyl 2-furyl H 707 methyl 2-furyl methyl 708 methyl 2-furyl ethyl 709 methyl 2-furyl propyl 710 methyl 2-furyl isopropyl 711 methyl 3-furyl H 712 methyl 3-furyl methyl 713 methyl 3-furyl ethyl 714 methyl 3-furyl propyl 715 methyl 3-furyl isopropyl 716 methyl 2-thienyl H 717 methyl 2-thienyl methyl 718 methyl 2-thienyl ethyl 719 methyl 2-thienyl propyl 720 methyl 2-thienyl isopropyl 721 methyl 3-thienyl H 722 methyl 3-thienyl methyl 723 methyl 3-thienyl ethyl 724 methyl 3-thienyl propyl 725 methyl 3-thienyl isopropyl

Song THE R ⁴ R ⁵ 726 methyl 2-oxazolyl H 727 methyl 2 cxazolil methyl 728 methyl 2-oxazolyl ethyl 729 methyl 2 cxazolii propyl 730 me 111 2-oxazolyl isopropyl 731 methyl 4-oxazolyl H 732 methyl 4-oxazolyl methyl 733 methyl 4-oxazolyl ethyl 734 methyl 4-oxazolyl propyl 735 methyl 4-oxazolyl isopropyl 736 methyl 2-thiazolyl H 737 methyl 2-thiazolyl methyl 738 methyl 2-thiazolyl ethyl 739 methyl 2-thiazolyl propyl 740 methyl 2-thiazolyl isopropyl 741 methyl 4-thiazolyl H 742 methyl 4-thiazolyl methyl 743 methyl 4-thiazolyl ethyl 744 methyl 4-thiazolyl propyl 745 methyl 4-thiazolyl isopropyl 746 methyl 3-isoxazolyl H 747 methyl 3-isoxazolyl methyl 748 methyl 3-isoxazolyl ethyl 749 methyl 3-isoxazolyl propyl 750 methyl 3-isoxazolyl isopropyl

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Song - 3 X R ⁴ R ⁵ 751 methyl 5-isoxazolyl H 752 methyl 5-isoxazolyl methyl 753 methyl 5-isoxazolyl ethyl 754 methyl 5-isoxazolyl propyl 755 methyl 5-isoxazolyl isopropyl 756 methyl 2-imidazolyl H 757 methyl 2-imidazolyl methyl 758 methyl 2-imidazolyl ethyl 759 methyl 2-imidazolyl propyl 760 methyl 2-imidazolyl isopropyl 761 methyl 3-pyrazolyl H 762 methyl 3-pyrazolyl methyl 763 methyl 3-pyrazolyl ethyl 764 methyl 3-pyrazolyl propyl 765 methyl 3-pyrazolyl isopropyl 766 methyl 4-pyrazolyl H 767 methyl 4-pyrazolyl methyl 768 methyl 4-pyrazolyl ethyl 769 methyl 4-pyrazolyl propyl 770 methyl 4-pyrazolyl isopropyl 771 methoxy H H 772 methoxy H methyl 773 methoxy H ethyl 774 methoxy H propyl 775 methoxy H isopropyl

• «· • · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · ·

Song R ³ R ⁴ R ⁵ 776 methoxy OH H 777 methoxy OH methyl 778 methoxy OH ethyl 779 methoxy OH propyl 780 methoxy OH isopropyl 781 methoxy chlorine butyl 782 methoxy chlorine methyl 783 methoxy chlorine ethyl 784 methoxy chlorine propyl 785 methoxy chlorine isopropyl 786 methoxy methoxy H 787 methoxy methoxy methyl 788 methoxy methoxy ethyl 789 methoxy methoxy propyl 790 methoxy methoxy isopropyl 791 methoxy methylthio H 792 methoxy methylthio methyl 793 methoxy methylthio ethyl 794 methoxy methylthio propyl 795 methoxy methylthio isopropyl 796 methoxy methyl H 797 methoxy methyl methyl 798 methoxy methyl ethyl 799 methoxy methyl propyl 8 00 methoxy methyl isopropyl

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Song R ³ R ⁴ R ⁵ 801 methoxy cyclopropyl H 802 methoxy cyclopropyl methyl 803 methoxy cyclopropyl ethyl 804 methoxy cyclopropyl propyl 805 methoxy cyclopropyl isopropyl 806 methoxy 2-pyridyl H 807 methoxy 2-pyridyl methyl 808 methoxy 2-pyridyl ethyl 809 methoxy 2-pyridyl propyl 810 methoxy 2-pyridyl isopropyl 811 methoxy 3-pyridyl H 812 methoxy 3-pyridyl methyl 813 methoxy 3-pyridyl ethyl 814 methoxy 3-pyridyl propyl 815 methoxy 3-pyridyl isopropyl 816 methoxy 4-pyridyl H 817 methoxy 4-pyridyl methyl 818 methoxy 4-pyridyl ethyl 819 methoxy 4-pyridyl propyl 820 methoxy 4-pyridyl isopropyl 821 methoxy 2-pyrimidinyl H 822 methoxy 2-pyrimidinyl methyl 823 methoxy 2-pyrimidinyl ethyl 824 methoxy 2-pyrimidinyl propyl 825 methoxy 2-pyrimidinyl isopropyl

Song R ³ R ⁴ R ⁵ 826 methoxy 4-pyrimidinylamino H 827 methoxy 4-pyrimidinyl ΓΠΘ vol 828 methoxy 4-pyrimidinylamino ethyl 829 methoxy 4-pyrimidinyl propyl 830 methoxy 4-pyrimidinyl isopropyl 831 methoxy 5-pyrimidinyl H 832 methoxy 5-pyrimidinyl methyl 833 methoxy 5-pyrimidinyl ethyl 834 methoxy 5-pyrimidinyl propyl 835 methoxy 5-pyrimidinyl isopropyl 836 methoxy 1,3,5-triazinyl H 837 methoxy 1,3,5-triazinyl methyl 838 methoxy 1,3,5-triazinyl ethyl 839 methoxy 1,3,5-triazinyl propyl 840 methoxy 1,3,5-triazinyl isopropyl 841 methoxy 2-furyl H 842 methoxy 2-furyl methyl 843 methoxy 2-furyl ethyl 844 methoxy 2-furyl propyl 845 methoxy 2-furyl isopropyl 846 methoxy 3-furyl H 847 methoxy 3-furyl methyl 848 methoxy 3-furyl ethyl 849 methoxy 3-furyl propyl 850 methoxy 3-furyl isopropyl

Song R ³ R ⁴ R ' 851 methoxy 2-thienyl H 852 methoxy 2-thienyl methyl 853 methoxy 2 oienil ethyl 854 methoxy 2-thienyl propyl 855 methoxy 2-thienyl isopropyl 856 methoxy 3-thienyl H 857 methoxy 3-thienyl methyl 858 methoxy 3-thienyl ethyl 859 methoxy 3-thienyl propyl 860 methoxy 3-thienyl isopropyl 8 61 methoxy 2-oxazolyl H 862 methoxy 2-oxazolyl methyl 863 methoxy 2-oxazolyl ethyl 864 methoxy 2-oxazolyl propyl 865 methoxy 2-oxazolyl isopropyl 866 methoxy 4-oxazolyl H 867 methoxy 4-oxazolyl methyl 868 methoxy 4-oxazolyl ethyl 869 methoxy 4-oxazolyl propyl 870 methoxy 4-oxazolyl isopropyl 871 methoxy 2-thiazolyl H 872 methoxy 2-thiazolyl methyl 873 methoxy 2-thiazolyl ethyl 874 methoxy 2-thiazolyl propyl 875 methoxy 2-thiazolyl isopropyl

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Song R ³ R ⁴ R ⁵ 876 methoxy 4-thiazolyl H 877 methoxy 4-thiazolyl methyl 878 methoxy 4-thiazolyl ethyl 879 methoxy 4-thiazolyl propyl 880 methoxy 4-thiazolyl isopropyl 881 methoxy 3-isoxazolyl H 882 methoxy 3-isoxazolyl methyl 883 methoxy 3-isoxazolyl ethyl 884 methoxy 3-Zoxazolyl propyl 8 8 5 me toxi 3-isoxazolyl isopropyl 886 methoxy 5-isoxazolyl H 887 methoxy 5-isoxazolyl methyl 888 methoxy 5-isoxazolyl ethyl 88 9 methoxy 5-isoxazolyl propyl 890 methoxy 5-isoxazolyl isopropyl 891 methoxy 2-imidazolyl H 892 methoxy 2-imidazolyl methyl 893 methoxy 2-imidazolyl ethyl 894 methoxy 2-imidazolyl propyl 895 methoxy 2-imidazolyl isopropyl 896 methoxy 3-pyrazolyl H 897 methoxy 3-pyrazolyl methyl 898 methoxy 3-pyrazolyl ethyl 899 methoxy 3-pyrazolyl propyl 900 methoxy 3-pyrazolyl isopropyl

Song R ³ R ⁴ R ⁵ 901 methoxy 4-pyrazolyl H 902 methoxy 4-pyrazolyl methyl 903 methoxy 4-pyrazolyl ethyl 904 methoxy 4-pyrazolyl propyl 905 methoxy 4-pyrazolyl isopropyl 906 OH H H 907 OH H methyl 908 OH H ethyl 909 OH H propyl 910 OH H isopropyl 911 OH OH H 912 OH OH methyl 913 OH OH ethyl 914 OH OH propyl 915 OH OH isopropyl 916 OH chlorine butyl 917 OH chlorine methyl 918 OH chlorine ethyl 919 OH chlorine propyl 920 OH chlorine isopropyl 921 OH methoxy H 922 OH methoxy methyl 923 OH methoxy ethyl 924 OH methoxy propyl 925 OH methoxy isopropyl

··· * ·

6Ί

Song R ³ R ⁴ R ⁵ 926 OH methylthio H 927 OH methylthio methyl 928 OH methylthio ethyl 92 9 OH methylthio propyl 930 OH we til-thio isopropyl 931 OH methyl H 932 OH methyl methyl 933 OH methyl ethyl 934 OH methyl propyl 935 OH methyl isopropyl 936 OH cyclopropyl H 937 OH cyclopropyl methyl 938 OH cyclopropyl ethyl 939 OH cyclopropyl propyl 940 OH cyclopropyl isopropyl 941 OH 2-pyridyl H 942 OH 2-pyridyl methyl 943 OH 2-pyridyl ethyl 944 OH 2-pyridyl propyl 945 OH 2-pyridyl isopropyl 946 OH 3-pyridyl H 947 OH 3-pyridyl methyl 948 OH 3-pyridyl ethyl 949 OH 3-pyridyl propyl 950 OH 3-pyridyl isopropyl

···· "

Song R ³ R ⁴ R ⁵ 951 OH 4-pyridyl H 952 OH 4-pyridyl methyl 953 OH 4-pyridyl ethyl 954 OH 4-pyridyl propyl 955 OH 4-pyridyl isopropyl 956 OH 2-pyrimidinyl H 957 OH 2-pyrimidinyl methyl 958 OH 2-pyrimidinyl ethyl 959 OH 2-pyrimidinyl propyl 960 OH 2-pyrimidinyl isopropyl 961 OH 4-pyrimidinyl H 962 OH 4-pyrimidinyl methyl 963 OH 4-pyrimidinyl ethyl 964 OH 4-pyrimidinyl propyl 965 OH 4-pyrimidinyl isopropyl 966 OH 5-pyrimidinyl H 967 OH 5-pyrimidinyl methyl 968 OH 5-pyrimidinyl ethyl 969 OH 5-pyrimidinyl propyl 970 OH 5-pyrimidinyl isopropyl 971 OH 1,3,5-triazinyl H 972 OH 1,3,5-triazinyl methyl 973 OH 1,3,5-triazinyl ethyl 974 OH 1,3,5-triazinyl propyl 975 OH 1,3,5-triazinyl isopropyl

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Song _3 X R ⁴ R ⁵ 976 OH 2-furyl H 977 OH 2-furyl methyl 978 OH 2-furyl ethyl 979 OH 2-furyl propyl 980 OH 2-furyl isopropyl 981 OH 3-furyl H 982 OH 3-furyl methyl 983 OH 3 fúri1 ethyl 984 OH 3-furyl propyl 985 OH 3-furyl isopropyl 986 OH 2-thienyl H 987 OH 2-thienyl methyl 988 OH 2-thienyl ethyl 989 OH 2-thienyl propyl 990 OH 2-thienyl isopropyl 991 OH 3-thienyl H 992 OH 3-thienyl methyl 993 OH 3-thienyl ethyl 994 OH 3-thienyl propyl 995 OH 3-thienyl isopropyl 996 OH 2-oxazolyl H 997 OH 2-oxazolyl methyl 998 OH 2-oxazolyl ethyl 999 OH 2-oxazolyl propyl 1000 OH 2-oxazolyl isopropyl

• ·

Song R ³ R ⁴ R ⁵ 1001 OH 4-oxazolyl H 1002 OH 4-oxazolyl methyl 1003 OH 4-oxazolyl ethyl 1004 OH 4 cxazolil propyl 1005 OH 4 cxazolil isopropyl 1006 OH 2-thia zolil H 1007 OH 2-thiazolyl methyl 1008 OH 2-thiazolyl ethyl 1009 OH 2-thiazolyl propyl 1010 OH 2-thiazolyl isopropyl 1011 OH 4-thiazolyl H 1012 OH 4-thiazolyl methyl 1013 OH 4-thiazolyl ethyl 1014 OH 4-isoxazolyl propyl 1015 OH 4-isoxazolyl isopropyl 1016 OH 3-isoxazolyl H 1017 OH 3-isoxazolyl methyl 1018 OH 3-isoxazolyl ethyl 1019 OH 3-isoxazolyl propyl 1020 OH 3-isoxazolyl isopropyl 1021 OH 5-isoxazolyl H 1022 OH 5-isoxazolyl methyl 1023 OH 5-isoxazolyl ethyl 1024 OH 5-isoxazolyl propyl 1025 OH 5-isoxazolyl isopropyl

• · ·· ·

Song R ³ R ⁴ R ⁵ 1026 OH 2-imidazolyl H 1027 OH 2-imidazolyl methyl 1028 OH 2-imidazolyl ethyl 1029 OH 2-imidazolyl propyl 1030 OH 2-imidazolyl isopropyl 1031 OH 3-pyrazolyl H 1032 OH 3-pyrazolyl methyl 1033 OH 3-pyrazolyl ethyl 1034 OH 3-pyrazolyl propyl 10 35 OH 3-pyrazolyl isopropyl 1036 OH 4-pyrazolyl H 1037 OH 4-pyrazolyl methyl 1038 OH 4-pyrazolyl ethyl 1039 OH 4-pyrazolyl propyl 1040 OH 4-pyrazolyl isopropyl 1041 H H H 1042 H H methyl 1043 H H ethyl 1044 H H propyl 1045 H H isopropyl 1046 H OH H 1047 H OH methyl 1048 H OH ethyl 1049 H OH propyl 1050 H OH isopropyl

Song R ³ R ⁴ R ⁵ 1051 H chlorine butyl 1052 H chlorine methyl 1053 H chlorine ethyl 1054 H chlorine propyl 1055 H chlorine isopropyl 1056 H methoxy H 1057 H methoxy methyl 1058 H methoxy ethyl 1059 H methoxy propyl 1060 H methoxy isopropyl 1061 H methyl H 1062 H methyl methyl 1063 H methyl ethyl 1064 H methyl propyl 1065 H methyl isopropyl 1066 H cyclopropyl H 1067 H cyclopropyl methyl 1068 H cyclopropyl ethyl 1069 H cyclopropyl propyl 1070 H cyclopropyl isopropyl 1071 chlorine H H 1072 chlorine H methyl 1073 chlorine H ethyl 1074 chlorine H propyl 1075 chlorine H isopropyl

Song R ³ R ⁴ R ⁵ 1076 chlorine OH H 1077 chlorine OH methyl 1078 chlorine OH ethyl 1079 chlorine OH propyl 1080 chlorine OH isopropyl 1081 chlorine chlorine butyl 1082 chlorine chlorine methyl 1083 chlorine chlorine ethyl 1084 chlorine chlorine propyl 1085 chlorine chlorine isopropyl 1086 chlorine methoxy H 1087 chlorine methoxy methyl 1088 chlorine methoxy ethyl 1089 chlorine methoxy propyl 1090 chlorine methoxy isopropyl 1091 chlorine methyl H 1092 chlorine methyl methyl 1093 chlorine methyl ethyl 1094 chlorine methyl propyl 1095 chlorine methyl isopropyl 1096 chlorine cyclopropyl H 1097 chlorine cyclopropyl methyl 1098 chlorine cyclopropyl ethyl 1099 chlorine cyclopropyl propyl 1100 chlorine cyclopropyl isopropyl

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Song R ³ R ⁴ R ⁵ 1101 methyl- K H 1102 methyl- thio H methyl 1103 methyl- - t i c H ethyl 1104 methyl- thio H propyl 1105 methyl- thio H isopropyl 1106 me t i1- thio OH H 1107 methyl- thio OH methyl 1108 methyl- thio OH ethyl 1109 methyl- thio OH propyl 1110 methyl- thio OH isopropyl 1111 methyl- thio methyl H 1112 methyl- thio methyl methyl 1113 methyl- methyl ethyl

Song R ³ R ⁴ R ⁵ thio 1114 methyl thio methyl propyl 1115 met11- thio methyl isopropyl 1116 methyl- thio methylthio H 1117 methyl- thio methylthio methyl 1118 methyl- thio methylthio ethyl 1119 methyl- thio methylthio propyl 1120 methyl- thio methylthio isopropyl 1121 methyl- -t io cyclopropyl H 1122 methyl- thio cyclopropyl methyl 1123 methyl- thio cyclopropyl ethyl 1124 methyl- thio cyclopropyl propyl 1125 methyl- thio cyclopropyl isopropyl

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Song R ³ R ⁴ R ^S 1126 cyclo propyl · H H 1127 cyclo propyl H methyl 1128 cyclo propyl H ethyl 1129 cyclo propyl H propyl 1130 cyclo propyl H isopropyl 1131 cyclo propyl · OH H 1132 cyclo propyl OH methyl 1133 cyclo propyl OH ethyl 1134 cyclo propyl OH propyl 1135 cyclo propyl OH isopropyl 1136 cyclo propyl chlorine butyl 1137 cyclo propyl chlorine methyl 1138 cyclo chlorine ethyl

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Song R ³ R ⁴ R ⁵ propyl 1139 cyclo propyl chlorine propyl 1140 cyclo propyl chlorine isopropyl 1141 cyclo propyl methoxy H 1142 cyclo propyl methoxy methyl 1143 cyclo propyl methoxy ethyl 1144 cyclo propyl methoxy propyl 1145 cyclo propyl methoxy isopropyl 1146 cyclo propyl methylthio H 1147 cyclo propyl methylthio methyl 1148 cyclo propyl methylthio ethyl 1149 cyclo propyl methylthio propyl 1150 cyclo propyl methylthio isopropyl

Song R ³ R ⁴ R ⁵ 1151 cyclo propyl methyl H 1152 cyclo propyl methyl methyl 1153 cyclo propyl methyl ethyl 1154 cyclo propyl methyl propyl 1155 cyclo propyl methyl isopropyl 1156 methyl 2-fluorophenyl H 1157 methyl 2-fluorophenyl methyl 1158 methyl 2-fluorophenyl ethyl 1159 methyl 2-fluorophenyl propyl 1160 methyl 2-fluorophenyl isopropyl 1161 methyl 2-fluorophenyl butyl 1162 methyl 2-fluorophenyl tert-butyl 1163 methyl 2-fluorophenyl hexyl 1164 methyl 2-fluorophenyl allyl 1165 methyl 2-fluorophenyl (E) -3-chloro-allyl 1166 methyl 2-fluorophenyl propynyl 1167 methyl 2-fluorophenyl 3-methyl-2-butenyl 1168 methyl 3-fluorophenyl H 1169 methyl 3-fluorophenyl methyl 1170 methyl 3-fluorophenyl ethyl

Song R ³ R ⁴ R ⁵ 1171 methyl 3-fluorophenyl propyl 1172 methyl 3-fluorophenyl isopropyl 1173 methyl 3-fluorophenyl butyl 1174 methyl 3-fluorophenyl tert-butyl 1175 methyl 3-fluorophenyl hexyl 1176 methyl 3-fluorophenyl allyl 1177 methyl 3-fluorophenyl (E) -3-chloro-allyl 1178 methyl 3-fluorophenyl propynyl 1179 methyl 3-fluorophenyl 3-methyl-2-butenyl 1180 methyl 4-fluorophenyl H 1181 methyl 4-fluorophenyl methyl 1182 methyl 4-fluorophenyl ethyl 1183 methyl 4-fluorophenyl propyl 1184 methyl 4-fluorophenyl isopropyl 1185 methyl 4-fluorophenyl butyl 1186 methyl 4-fluorophenyl tert-butyl 1187 methyl 4-fluorophenyl hexyl 1188 methyl 4-fluorophenyl allyl 1189 methyl 4-fluorophenyl (E) -3-chloro-allyl 1190 methyl 4-fluorophenyl propynyl 1191 methyl 4-fluorophenyl 3-methyl-2-butenyl 1192 methyl 2-chlorophenyl H 1193 methyl 2-chlorophenyl methyl 1194 methyl 2-chlorophenyl ethyl 1195 methyl 2-chlorophenyl propyl

t 80

T

Song R ³ R ⁴ R ⁵ 1196 methyl 2-chlorophenyl isopropyl 1197 methyl 2-chlorophenyl butyl 1198 methyl 2-chlorophenyl tert-butyl 1199 methyl 2-chlorophenyl hexyl 1200 methyl 2-chlorophenyl allyl 1201 methyl 2-chlorophenyl (E) -3-chloro-allyl 1202 methyl 2-chlorophenyl propynyl 1203 methyl 2-chlorophenyl 3-methyl-2-butenyl 1204 methyl 3-chlorophenyl H 1205 methyl 3-chlorophenyl methyl 1206 methyl 3-chlorophenyl ethyl 1207 methyl 3-chlorophenyl propyl 1208 methyl 3-chlorophenyl isopropyl 1209 methyl 3-chlorophenyl butyl 1210 methyl 3-chlorophenyl tert-butyl 1211 methyl 3-chlorophenyl hexyl 1212 methyl 3-chlorophenyl allyl 1213 methyl 3-chlorophenyl (E) -3-chloro-allyl 1214 methyl 3-chlorophenyl propynyl 1215 methyl 3-chlorophenyl 3-methyl-2-butenyl 1216 methyl 4-chlorophenyl H 1217 methyl 4-chlorophenyl methyl 1218 methyl 4-chlorophenyl ethyl 1219 methyl 4-chlorophenyl propyl 1220 methyl 4-chlorophenyl isopropyl

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Song R ³ R ⁴ R ⁵ 1221 methyl 4-chlorophenyl butyl 1222 methyl 4-chlorophenyl tert-butyl 1223 methyl 4-chlorophenyl hexyl 1224 methyl 4-chlorophenyl allyl 1225 methyl 4-chlorophenyl (E) -3-chloro-allyl 1226 methyl 4-chlorophenyl propynyl 1227 methyl 4-chlorophenyl 3-methyl-2-cool 1 1228 methyl 2,3-dichlorophenyl H 1229 methyl 2,3-dichlorophenyl methyl 1230 methyl 2,3-dichlorophenyl ethyl 1231 methyl 2,3-dichlorophenyl propyl 1232 methyl 2,3-dichlorophenyl isopropyl 1233 methyl 2,3-dichlorophenyl butyl 1234 methyl 2,3-dichlorophenyl tert-butyl 1235 methyl 2,3-dichlorophenyl hexyl 1236 methyl 2,3-dichlorophenyl allyl 1237 methyl 2,3-dichlorophenyl (E) -3-chloro-allyl 1238 methyl 2,3-dichlorophenyl propynyl 1239 methyl 2,3-dichlorophenyl 3-methyl-2-butenyl 1240 methyl 2,4-dichlorophenyl H 1241 methyl 2,4-dichlorophenyl methyl 1242 methyl 2,4-dichlorophenyl ethyl 1243 methyl 2,4-dichlorophenyl propyl 1244 methyl 2,4-dichlorophenyl isopropyl 1245 methyl 2,4-dichlorophenyl butyl

Song R ³ R ⁴ ς R ^J 1246 methyl 2,4-dichlorophenyl tert-butyl 1247 methyl 2,4-dichlorophenyl hexyl 1248 methyl 2,4-dichlorophenyl allyl 1249 methyl 2,4-dichlorophenyl (E) -3-chloro-allyl 1250 methyl 2,4-dichlorophenyl propynyl 1251 methyl 2,4-dichlorophenyl 3-methyl-2-butenyl 1252 methyl 2,5-dichlorophenyl H 1253 methyl 2,5-dichlorophenyl methyl 1254 methyl 2,5-dichlorophenyl ethyl 1255 methyl 2,5-dichlorophenyl propyl 1256 methyl 2,5-dichlorophenyl isopropyl 1257 methyl 2,5-dichlorophenyl butyl 1258 methyl 2,5-dichlorophenyl tert-butyl 1259 methyl 2,5-dichlorophenyl hexyl 1260 methyl 2,5-dichlorophenyl allyl 1261 methyl 2,5-dichlorophenyl (E) -3-chloro-allyl 1262 methyl 2,5-dichlorophenyl propynyl 1263 methyl 2,5-dichlorophenyl 3-methyl-2-butenyl 1264 methyl 2,6-dichlorophenyl H 1265 methyl 2,6-dichlorophenyl methyl 1266 methyl 2,6-dichlorophenyl ethyl 1267 methyl 2,6-dichlorophenyl propyl 1268 methyl 2,6-dichlorophenyl isopropyl 1269 methyl 2,6-dichlorophenyl butyl 1270 methyl 2,6-dichlorophenyl tert-butyl

Song R ³ R ⁴ R ⁵ 1271 methyl 2,6-dichlorophenyl hexyl 1272 methyl 2,6-dichlorophenyl allyl 1273 methyl 2,6-dichlorophenyl (E) -3-chloro-allyl 1274 methyl 2,6-dichlorophenyl propynyl 1275 methyl 2,6-dichlorophenyl 3-methyl-2-butenyl 1276 methyl 3,4-dichlorophenyl H 1277 methyl 3,4-dichlorophenyl methyl 1278 methyl 3,4-dichlorophenyl ethyl 1279 methyl 3,4-dichlorophenyl propyl 1280 methyl 3,4-dichlorophenyl isopropyl 1281 methyl 3,4-dichlorophenyl butyl 1282 methyl 3,4-dichlorophenyl tert-butyl 1283 methyl 3,4-dichlorophenyl hexyl 1284 methyl 3,4-dichlorophenyl allyl 1285 methyl 3,4-dichlorophenyl (E) -3-chloro-allyl 1286 methyl 3,4-dichlorophenyl propynyl 1287 methyl 3,4-dichlorophenyl 3-methyl-2-butenyl 1288 methyl 3,5-dichlorophenyl H 1289 methyl 3,5-dichlorophenyl methyl 1290 methyl 3,5-dichlorophenyl ethyl 1291 methyl 3,5-dichlorophenyl propyl 1292 methyl 3,5-dichlorophenyl isopropyl 1293 methyl 3,5-dichlorophenyl butyl 1294 methyl 3,5-dichlorophenyl tert-butyl 1295 methyl 3,5-dichlorophenyl hexyl

Song R ³ R ⁴ R ⁵ 1296 methyl 3,5-dichlorophenyl allyl 1297 methyl 3,5-dichlorophenyl (E) -3-chloro-allyl 1298 methyl 3,5-dichlorophenyl propynyl 1299 methyl 3,5-dichlorophenyl 3-methyl-2-butenyl 1300 methyl 2-bromophenyl H 1301 methyl 2-bromophenyl methyl 1302 methyl 2-bromophenyl ethyl 1303 methyl 2-bromophenyl propyl 1304 methyl 2-bromophenyl isopropyl 1305 methyl 2-bromophenyl butyl 1306 methyl 2-bromophenyl tert-butyl 1307 methyl 2-bromophenyl hexyl 1308 methyl 2-bromophenyl allyl 1309 methyl 2-bromophenyl (E) -3-chloro-allyl 1310 methyl 2-bromophenyl propynyl 1311 methyl 2-bromophenyl 3-methyl-2-butenyl 1312 methyl 3-bromophenyl H 1313 methyl 3-bromophenyl methyl 1314 methyl 3-bromophenyl ethyl 1315 methyl 3-bromophenyl propyl 1316 methyl 3-bromophenyl isopropyl 1317 methyl 3-bromophenyl butyl 1318 methyl 3-bromophenyl tert-butyl 1319 methyl 3-bromophenyl hexyl 1320 methyl 3-bromophenyl allyl

Song R ³ R ⁴ R ⁵ 1321 methyl 3-bromophenyl (E) -3-chloro-allyl 1322 methyl 3-bromophenyl propynyl 1323 methyl 3-bromophenyl 3-methyl-2-butenyl 1324 methyl 4-bromophenyl H 1325 methyl 4-bromophenyl methyl 1326 methyl 4-bromophenyl ethyl 1327 methyl 4-bromophenyl propyl 1328 methyl 4-bromophenyl isopropyl 1329 methyl 4-bromophenyl butyl 1330 methyl 4-bromophenyl tert-butyl 1331 methyl 4-bromophenyl hexyl 1332 methyl 4-bromophenyl allyl 1333 methyl 4-bromophenyl (E) -3-chloro-allyl 1334 methyl 4-bromophenyl propynyl 1335 methyl 4-bromophenyl 3-methyl-2-butenyl 1336 methyl 2-iodophenyl H 1337 methyl 2-iodo-phenyl methyl 1338 methyl 2-iodo-phenyl ethyl 1339 methyl 2-iodo-phenyl propyl 1340 methyl 2-iodophenyl isopropyl 1341 methyl 2-iodophenyl butyl 1342 methyl 2-iodo-phenyl tert-butyl 1343 methyl 2-iodophenyl hexyl 1 1344 methyl 2-iodophenyl allyl 1345 methyl 2-iodo-phenyl (E) -3-chloro-allyl

Song R ³ R ⁴ R ⁵ 1346 methyl 2-iodo-phenyl propynyl 1347 methyl 2-iodo-phenyl 3-methyl-2-butenyl 1348 methyl 3-iodophenyl H 1349 methyl 3-iodophenyl methyl 1350 methyl 3-iodophenyl ethyl 1351 methyl 3-iodophenyl propyl 1352 methyl 3-iodophenyl isopropyl 1353 methyl 3-iodophenyl butyl 1354 methyl 3-iodophenyl tert-butyl 1355 methyl 3-iodophenyl hexyl 1356 methyl 3-iodophenyl allyl 1357 methyl 3-iodophenyl (E) -3-chloro-allyl 1358 methyl 3-iodophenyl propynyl 1359 methyl 3-iodophenyl 3-methyl-2-butenyl 1360 methyl 4-iodo-phenyl H 1361 methyl 4-iodo-phenyl methyl 1362 methyl 4-iodophenyl ethyl 1363 methyl 4-iodo-phenyl propyl 1364 methyl 4-iodophenyl isopropyl 1365 methyl 4-iodo-phenyl butyl 1366 methyl 4-iodo-phenyl tert-butyl 1367 methyl 4-iodophenyl hexyl 1368 methyl 4-iodo-phenyl allyl 1369 methyl 4-iodo-phenyl (E) -3-chloro-allyl 1370 methyl 4-iodophenyl propynyl

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Song R ³ R ⁴ R ⁵ 1371 methyl 4-iodophenyl 3-methyl-2-butenyl 1372 methyl 2-cyanophenyl H 1373 methyl 2-cyanophenyl methyl 1374 methyl 2-cyanophenyl ethyl 1375 methyl 2-cyanophenyl propyl 1376 methyl 2-cyanophenyl isopropyl 1377 methyl 2-cyanophenyl butyl 1378 methyl 2-cyanophenyl tert-butyl 1379 methyl 2-cyanophenyl hexyl 1380 methyl 2-cyanophenyl allyl 1381 methyl 2-cyanophenyl (E) -3-chloro-allyl 1382 methyl 2-cyanophenyl propynyl 1383 methyl 2-cyanophenyl 3-methyl-2-butenyl 1384 methyl 3-cyanophenyl H 1385 methyl 3-cyanophenyl methyl 1386 methyl 3-cyanophenyl ethyl 1387 methyl 3-cyanophenyl propyl 1388 methyl 3-cyanophenyl isopropyl 1389 methyl 3-cyanophenyl butyl 1390 methyl 3-cyanophenyl tert-butyl 1391 methyl 3-cyanophenyl hexyl 1392 methyl 3-cyanophenyl allyl 1393 methyl 3-cyanophenyl (E) -3-chloro-allyl 1394 methyl 3-cyanophenyl propynyl 1395 methyl 3-cyanophenyl 3-methyl-2-butenyl

Song R ³ R ⁴ R ⁵ 13 96 methyl 4-cyanophenyl H 1397 methyl 4-cyanophenyl methyl 1398 methyl 4-cyanophenyl ethyl 1399 methyl 4-cyanophenyl propyl 1400 methyl 4-cyanophenyl isopropyl 1401 methyl 4-cyanophenyl butyl 1402 methyl 4-cyanophenyl tert-butyl 1403 methyl 4-cyanophenyl hexyl 1404 methyl 4-cyanophenyl allyl 1405 methyl 4-cyanophenyl (E) -3-chloro-allyl 1406 methyl 4-cyanophenyl propynyl 1407 methyl 4-cyanophenyl 3-butenyl metí1-2 1408 methyl 2-nitrophenyl H 1409 methyl 2-nitrophenyl methyl 1410 methyl 2-nitrophenyl ethyl 1411 methyl 2-nitrophenyl propyl 1412 methyl 2-nitrophenyl isopropyl 1413 methyl 2-nitrophenyl butyl 1414 methyl 2-nitrophenyl tert-butyl 1415 methyl 2-nitrophenyl hexyl 1416 methyl 2-nitrophenyl allyl 1417 methyl 2-nitrophenyl (E) -3-chloro-allyl 1418 methyl 2-nitrophenyl propynyl 1419 methyl 2-nitrophenyl 3-methyl-2-butenyl 1420 methyl 3-nitrophenyl H

Song R ³ R ⁴ R ⁵ 1421 methyl 3-nitrophenyl methyl 1422 methyl 3-nitrophenyl ethyl 1423 methyl 3-nitrophenyl propyl 1424 methyl 3-nitrophenyl isopropyl 1425 methyl 3-nitrophenyl butyl 1426 methyl 3-nitrophenyl tert-butyl 1427 methyl 3-nitrophenyl hexyl 1428 methyl 3-nitrophenyl allyl 1429 methyl 3-nitrophenyl (E) -3-chloro-allyl 1430 methyl 3-nitrophenyl propynyl 1431 methyl 3-nitrophenyl 3-methyl-2-butenyl 1432 methyl 4-nitrophenyl H 1433 methyl 4-nitrophenyl methyl 1434 methyl 4-nitrophenyl ethyl 1435 methyl 4-nitrophenyl propyl 1436 methyl 4-nitrophenyl isopropyl 1437 methyl 4-nitrophenyl butyl 1438 methyl 4-nitrophenyl tert-butyl 1439 methyl 4-nitrophenyl hexyl 1440 methyl 4-nitrophenyl allyl 1441 methyl 4-nitrophenyl (E) -3-chloro-allyl 1442 methyl 4-nitrophenyl propynyl 1443 methyl 4-nitrophenyl 3-methyl-2-butenyl 1444 methyl 2-methylphenyl H 1445 methyl 2-methylphenyl methyl

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Song R ³ R ⁴ R ⁵ 1446 methyl 2-methylphenyl ethyl 1447 methyl 2-methylphenyl propyl 1448 methyl 2-methyl-fení1 isopropyl 1449 methyl 2-methylphenyl butyl 1450 methyl 2-methylphenyl tert-butyl 1451 methyl 2-methylphenyl hexyl 1452 methyl 2-methylphenyl allyl 1453 methyl 2-methylphenyl (E) -3-chloro-allyl 1454 methyl 2-methylphenyl propynyl 1455 methyl 2-methylphenyl 3-methyl-2-butenyl 1456 methyl 3-methylphenyl H 1457 methyl 3-methylphenyl methyl 1458 methyl 3-methylphenyl ethyl 1459 methyl 3-methylphenyl propyl 1460 methyl 3-methylphenyl isopropyl 1461 methyl 3-methylphenyl butyl 1462 methyl 3-methylphenyl tert-butyl 1463 methyl 3-methylphenyl hexyl 1464 methyl 3-methylphenyl allyl 1465 methyl 3-methylphenyl (E) -3-chloro-allyl 1466 methyl 3-methylphenyl propynyl 1467 methyl 3-methylphenyl 3-methyl-2-butenyl 1468 methyl 4-methylphenyl H 1469 methyl 4-methylphenyl methyl 1470 methyl 4-methylphenyl ethyl

Song R ³ R ⁴ R ⁵ 1471 methyl 4-methylphenyl propyl 1472 methyl 4-methylphenyl isopropyl 1473 methyl 4-methylphenyl butyl 1474 methyl 4-methylphenyl tert-butyl 1475 methyl 4-methylphenyl hexyl 1476 methyl 4-methylphenyl allyl 1477 methyl 4-methylphenyl (E) -3-chloro-allyl 1478 methyl 4-methylphenyl propynyl 1479 methyl 4-methylphenyl 3-methyl-2-butenyl 1480 methyl 2,3-dimethylphenyl H 1481 methyl 2,3-dimethylphenyl methyl 1482 methyl 2,3-dimethylphenyl ethyl 1483 methyl 2,3-dimethylphenyl propyl 1484 methyl 2,3-dimethylphenyl isopropyl 1485 methyl 2,3-dimethylphenyl butyl 1486 methyl 2,3-dimethylphenyl tert-butyl 1487 methyl 2,3-dimethylphenyl hexyl 1488 methyl 2,3-dimethylphenyl allyl 1489 methyl 2,3-dimethylphenyl (E) -3-chloro-allyl 1490 methyl 2,3-dimethylphenyl propynyl 1491 methyl 2,3-dimethylphenyl 3-methyl-2-butenyl 1492 methyl 2,4-dimethylphenyl H 1493 methyl 2,4-dimethylphenyl methyl 1494 methyl 2,4-dimethylphenyl ethyl 1495 methyl 2,4-dimethylphenyl propyl

Song R ³ R ⁴ R ⁵ 1496 methyl 2,4-dimethylphenyl isopropyl 1497 methyl 2,4-dimethylphenyl butyl 1498 methyl 2,4-dimethylphenyl tert-butyl 1499 methyl 2,4-dimethylphenyl hexyl 1500 methyl 2,4-dimethylphenyl allyl 1501 methyl 2,4-dimethylphenyl (E) -3-chloro-allyl 1502 methyl 2,4-dimethylphenyl propynyl 1503 methyl 2,4-dimethylphenyl 3-methyl-2-butenyl 1504 methyl 2,5-dimethylphenyl H 1505 methyl 2,5-dimethylphenyl methyl 1506 methyl 2,5-dimethylphenyl ethyl 1507 methyl 2,5-dimethylphenyl propyl 1508 methyl 2,5-dimethylphenyl isopropyl 1509 methyl 2,5-dimethylphenyl butyl 1510 methyl 2,5-dimethylphenyl tert-butyl 1511 methyl 2,5-dimethylphenyl hexyl 1512 methyl 2,5-dimethylphenyl allyl 1513 methyl 2,5-dimethylphenyl (E) -3-chloro-allyl 1514 methyl 2,5-dimethylphenyl propynyl 1515 methyl 2,5-dimethylphenyl 3-methyl-2-butenyl 1516 methyl 2,6-dimethylphenyl H 1517 methyl 2,6-dimethylphenyl methyl 1518 methyl 2,6-dimethylphenyl ethyl 1519 methyl 2,6-dimethylphenyl propyl 1520 methyl 2,6-dimethylphenyl isopropyl

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Song R ³ R ⁴ R ⁵ 1521 methyl 2,6-dimethylphenyl butyl 1522 methyl 2,6-dimethylphenyl tert-butyl 1523 methyl 2,6-dimethylphenyl hexyl 1524 methyl 2,6-dimethylphenyl allyl 1525 methyl 2,6-dimethylphenyl (E) -3-chloro-allyl 1526 methyl 2,6-dimethylphenyl propynyl 1527 methyl 2,6-dimethylphenyl 3-methyl-2-butenyl 1528 methyl 3,4-dimethylphenyl H 1529 methyl 3,4-dimethylphenyl methyl 1530 methyl 3,4-dimethylphenyl ethyl 1531 methyl 3,4-dimethylphenyl propyl 1532 methyl 3,4-dimethylphenyl isopropyl 1533 methyl 3,4-dimethylphenyl butyl 1534 methyl 3,4-dimethylphenyl tert-butyl 1535 methyl 3,4-dimethylphenyl hexyl 1536 methyl 3,4-dimethylphenyl allyl 1537 methyl 3,4-dimethylphenyl (E) -3-chloro-allyl 1538 methyl 3,4-dimethylphenyl propynyl 1539 methyl 3,4-dimethylphenyl 3-methyl-2-butenyl 1540 methyl 3,5-dimethylphenyl H 1541 methyl 3,5-dimethylphenyl methyl 1542 methyl 3,5-dimethylphenyl ethyl 1543 methyl 3,5-dimethylphenyl propyl 1544 methyl 3,5-dimethylphenyl isopropyl 1545 methyl 3,5-dimethylphenyl butyl

Song R ³ R ⁴ R ⁵ 1546 methyl 3,5-dimethylphenyl tert-butyl 1547 methyl 3,5-dimethylphenyl hexyl 1548 methyl 3,5-dimethylphenyl allyl 1549 methyl 3,5-dimethylphenyl (E) -3-chloro-allyl 1550 methyl 3,5-dimethylphenyl propynyl 1551 methyl 3,5-dimethylphenyl 3-methyl-2-butenyl 1552 methyl 2-ethylphenyl H 1553 methyl 2-ethylphenyl methyl 1554 methyl 2-ethylphenyl ethyl 1555 methyl 2-ethylphenyl propyl 1556 methyl 2-ethylphenyl isopropyl 1557 methyl 2-ethylphenyl butyl 1558 methyl 2-ethylphenyl tert-butyl 1559 methyl 2-ethylphenyl hexyl 1560 methyl 2-ethylphenyl allyl 1561 methyl 2-ethylphenyl (E) -3-chloro-allyl 1562 methyl 2-ethylphenyl propynyl 1563 methyl 2-ethylphenyl 3-methyl-2-butenyl 1564 methyl 3-ethylphenyl H 1565 methyl 3-ethylphenyl methyl 1566 methyl 3-ethylphenyl ethyl 1567 methyl 3-ethylphenyl propyl 1568 methyl 3-ethylphenyl isopropyl 1569 methyl 3-ethylphenyl butyl 1570 methyl 3-ethylphenyl tert-butyl

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Song R ³ R ⁴ R ⁵ 1571 methyl 3-ethylphenyl hexyl 1572 methyl 3-ethylphenyl allyl 1573 methyl 3-ethylphenyl (E) -3-chloro-allyl 1574 methyl 3-ethylphenyl propynyl 1575 methyl 3-ethylphenyl 3-methyl-2-butenyl 1576 methyl 4-ethylphenyl H 1577 methyl 4-ethylphenyl methyl 1578 methyl 4-ethylphenyl ethyl 1579 methyl 4-ethylphenyl propyl 1580 methyl 4-ethylphenyl isopropyl 1581 methyl 4-ethylphenyl butyl 1582 methyl 4-ethylphenyl tert-butyl 1583 methyl 4-ethylphenyl hexyl 1584 methyl 4-ethylphenyl allyl 1585 methyl 4-ethylphenyl (E) -3-chloro-allyl 1586 methyl 4-ethylphenyl propynyl 1587 methyl 4-ethylphenyl 3-methyl-2-butenyl 1588 methyl 2-isopropylphenyl H 1589 methyl 2-isopropylphenyl methyl 1590 methyl 2-isopropylphenyl ethyl 1591 methyl 2-isopropylphenyl propyl 1592 methyl 2-isopropylphenyl isopropyl 1593 methyl 2-isopropylphenyl butyl 1594 methyl 2-isopropylphenyl tert-butyl 1595 methyl 2-isopropylphenyl hexyl

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Song R ³ R ⁴ R ⁵ 1596 methyl 2-isopropylphenyl allyl 1597 methyl 2-1zopropil-phenyl (E) -3-chloro-allyl 1598 methyl 2-isopropylphenyl propynyl 1599 methyl 2-1zopropil-phenyl 3-methyl-2-butenyl 1600 methyl 3-Isopropylphenyl H 1601 methyl 3-isopropylphenyl methyl 1602 methyl 3-isopropylphenyl ethyl 1603 methyl 3-isopropylphenyl propyl 1604 methyl 3-isopropylphenyl isopropyl 1605 methyl 3-isopropylphenyl butyl 1606 methyl 3-isopropylphenyl tert-butyl 1607 methyl 3-isopropylphenyl hexyl 1608 methyl 3-isopropylphenyl allyl 1609 methyl 3-isopropylphenyl (E) -3-chloro-allyl 1610 methyl 3-isopropylphenyl propynyl 1611 methyl 3-isopropylphenyl 3-methyl-2-butenyl 1612 methyl 4-isopropylphenyl H 1613 methyl 4-1zopropil-phenyl methyl 1614 methyl 4-isopropylphenyl ethyl 1615 methyl 4-1zopropil-phenyl propyl 1616 methyl 4-isopropylphenyl isopropyl 1617 methyl 4-isopropylphenyl butyl 1618 methyl 4-isopropylphenyl tert-butyl 1619 methyl 4-isopropylphenyl hexyl 1620 methyl 4-isopropylphenyl allyl

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Song R ³ R ⁴ R ⁵ 1621 methyl 4-isopropylphenyl (E) -3-chloro-allyl 1622 methyl 4-Isopropylphenyl propynyl 1623 methyl 4-isopropylphenyl 3-methyl-2-butenyl 1624 methyl 2-hydroxy-feni1 ' H 1625 methyl 2-hydroxyphenyl methyl 1626 methyl 2-hydroxyphenyl ethyl 1627 methyl 2-hydroxyphenyl propyl 1628 methyl 2-hydroxyphenyl isopropyl 1629 methyl 2-hydroxyphenyl butyl 1630 methyl 2-hydroxyphenyl tert-butyl 1631 methyl 2-hydroxyphenyl hexyl 1632 methyl 2-hydroxyphenyl allyl 1633 methyl 2-hydroxyphenyl (E) -3-chloro-allyl 1634 methyl 2-hydroxyphenyl propynyl 1635 methyl 2-hydroxyphenyl 3-methyl-2-butenyl 1636 methyl 3-hydroxyphenyl H 1637 methyl 3-hydroxyphenyl methyl 1638 methyl 3-hydroxyphenyl ethyl 1639 methyl 3-hydroxyphenyl propyl 1640 methyl 3-hydroxyphenyl isopropyl 1641 methyl 3-hydroxyphenyl butyl 1642 methyl 3-hydroxyphenyl tert-butyl 1643 methyl 3-hydroxyphenyl hexyl 1644 methyl 3-hydroxyphenyl allyl 1645 methyl 3-hydroxyphenyl (E) -3-chloro-allyl

Song R ³ R ⁴ R ⁵ 1646 methyl 3-hydroxyphenyl propynyl 1647 methyl 3-hydroxyphenyl 3-methyl-2-butenyl 1648 methyl 4-hydroxyphenyl H 1649 methyl 4-hydroxyphenyl methyl 1650 methyl 4-hydroxyphenyl ethyl 1651 methyl 4-hydroxyphenyl propyl 1652 methyl 4-hydroxyphenyl isopropyl 1653 methyl 4-hydroxyphenyl butyl 1654 methyl 4-hydroxyphenyl tert-butyl 1655 methyl 4-hydroxyphenyl hexyl 1656 methyl 4-hydroxyphenyl allyl 1657 methyl 4-hydroxyphenyl (E) -3-chloro-allyl 1658 methyl 4-hydroxyphenyl propynyl 1659 methyl 4-hydroxyphenyl 3-methyl-2-butenyl 1660 methyl 2-methoxyphenyl H 1661 methyl 2-methoxyphenyl methyl 1662 methyl 2-methoxyphenyl ethyl 1663 methyl 2-methoxyphenyl propyl 1664 methyl 2-methoxyphenyl isopropyl 1665 methyl 2-methoxyphenyl butyl 1666 methyl 2-methoxyphenyl tert-butyl 1667 methyl 2-methoxyphenyl hexyl 1668 methyl 2-methoxyphenyl allyl 1669 methyl 2-methoxyphenyl (E) -3-chloro-allyl 1670 methyl 2-methoxyphenyl propynyl

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Song R ³ R ⁴ R ⁵ 1671 methyl 2-methoxyphenyl 3-methyl-2-butenyl 1672 methyl 3-methoxyphenyl H 1673 methyl 3-methoxyphenyl methyl 1674 methyl 3-methoxyphenyl ethyl 1675 methyl 3-methoxyphenyl propyl 1676 methyl 3-methoxyphenyl isopropyl 1677 methyl 3-methoxyphenyl butyl 1678 methyl 3-methoxyphenyl tert-butyl 1679 methyl 3-methoxyphenyl hexyl 1680 methyl 3-methoxyphenyl allyl 1681 methyl 3-methoxyphenyl (E) -3-chloro-allyl 1682 methyl 3-methoxyphenyl propynyl 1683 methyl 3-methoxyphenyl 3-methyl-2-butenyl 1684 methyl 4-methoxyphenyl H 1685 methyl 4-methoxyphenyl methyl 1686 methyl 4-methoxyphenyl ethyl 1687 methyl 4-methoxyphenyl propyl 1688 methyl 4-methoxyphenyl isopropyl 1689 methyl 4-methoxyphenyl butyl 1690 methyl 4-methoxyphenyl tert-butyl 1691 methyl 4-methoxyphenyl hexyl 1692 methyl 4-methoxyphenyl allyl 1693 methyl 4-methoxyphenyl (E) -3-chloro-allyl 1694 methyl 4-methoxyphenyl propynyl 1695 methyl 4-methoxyphenyl 3-methyl-2-butenyl

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100 • ·

Song R ³ R ⁴ R ⁵ 1696 methyl 2-ethoxyphenyl H 1697 methyl 2-ethoxyphenyl methyl 1698 methyl 2-ethoxyphenyl ethyl 1699 methyl 2-ethoxyphenyl propyl 1700 methyl 2-ethoxyphenyl isopropyl 1701 methyl 2-ethoxy-phenol butyl 1702 methyl 2-ethoxyphenyl tert-butyl 1703 methyl 2-ethoxyphenyl hexyl 1704 methyl 2-ethoxyphenyl allyl 1705 methyl 2-ethoxyphenyl (E) -3-chloro-allyl 1706 methyl 2-ethoxyphenyl propynyl 1707 methyl 2-ethoxyphenyl 3-methyl-2-butenyl 1708 methyl 3-ethoxyphenyl H 1709 methyl 3-ethoxyphenyl methyl 1710 methyl 3-ethoxyphenyl ethyl 1711 methyl 3-ethoxyphenyl propyl 1712 methyl 3-ethoxyphenyl isopropyl 1713 methyl 3-ethoxyphenyl butyl 1714 methyl 3-ethoxyphenyl tert-butyl 1715 methyl 3-ethoxyphenyl hexyl 1716 methyl 3-ethoxyphenyl allyl 1717 methyl 3-ethoxyphenyl (E) -3-chloro-allyl 1718 methyl 3-ethoxyphenyl propynyl 1719 methyl 3-ethoxyphenyl 3-methyl-2-butenyl 1720 methyl 1 4-ethoxyphenyl H

• · · • · · · * «·

101 • ·

Song R ³ R ⁴ R ⁵ 1721 methyl 4-ethoxyphenyl methyl 1722 methyl 4-ethoxyphenyl ethyl 1723 methyl 4-ethoxyphenyl propyl 1724 methyl 4-ethoxyphenyl isopropyl 1725 methyl 4-ethoxyphenyl butyl 1726 methyl 4-ethoxyphenyl tert-butyl 1727 methyl 4-ethoxyphenyl hexyl 1728 methyl 4-ethoxyphenyl allyl 1729 methyl 4-ethoxyphenyl (E) -3-chloro-allyl 1730 methyl 4-ethoxyphenyl propynyl 1731 methyl 4-ethoxyphenyl 3-methyl-2-butenyl 1732 methyl 2-isopropoxyphenyl H 1733 methyl 2-isopropoxyphenyl methyl 1734 methyl 2-isopropoxyphenyl ethyl 1735 methyl 2-isopropoxyphenyl propyl 1736 methyl 2-isopropoxyphenyl isopropyl 1737 methyl 2-isopropoxyphenyl butyl 1738 methyl 2-isopropoxyphenyl tert-butyl 1739 methyl 2-isopropoxyphenyl hexyl 1740 methyl 2-isopropoxyphenyl allyl 1741 methyl 2-isopropoxyphenyl (E) -3-chloro-allyl 1742 methyl 2-isopropoxyphenyl propynyl 1743 methyl 2-isopropoxyphenyl 3-methyl-2-butenyl 1744 methyl 3-isopropoxyphenyl H 1745 methyl 3-isopropoxyphenyl methyl

102 • · · «

Song R ³ R ⁴ R ⁵ 1746 methyl 3-isopropoxyphenyl ethyl 1747 methyl 3-isopropoxyphenyl propyl 1748 methyl 3-isopropoxyphenyl isopropyl 1749 methyl 3-isopropoxyphenyl butyl 1750 methyl 3-isopropoxyphenyl tert-butyl 1751 methyl 3-isopropoxyphenyl hexyl 1752 methyl 3-isopropoxyphenyl allyl 1753 methyl 3-isopropoxyphenyl (E) -3-chloro-allyl 1754 methyl 3-isopropoxyphenyl propynyl 1755 methyl 3-isopropoxyphenyl 3-methyl-2-butenyl 1756 methyl 4-isopropoxyphenyl H 1757 methyl 4-isopropoxyphenyl methyl 1758 methyl 4-isopropoxyphenyl ethyl 1759 methyl 4-isopropoxyphenyl propyl 1760 methyl 4-isopropoxyphenyl isopropyl 1761 methyl 4-isopropoxyphenyl butyl 1762 methyl 4-isopropoxyphenyl tert-butyl 1763 methyl 4-isopropoxyphenyl hexyl 1764 methyl 4-isopropoxyphenyl allyl 1765 methyl 4-isopropoxyphenyl (E) -3-chloro-allyl 1766 methyl 4-isopropoxyphenyl propynyl 1767 methyl 4-isopropoxyphenyl 3-butenyl meti1-2 1768 methyl 2-tert-butoxyphenyl H 1769 methyl 2-tert-butoxyphenyl methyl 1770 methyl 2-tert-butoxyphenyl ethyl

103 • · • * · ·

Song R ³ R ⁴ R ⁵ 1771 methyl 2-tert-butoxyphenyl propyl 1772 methyl 2-tert-butoxyphenyl isopropyl 1773 methyl 2-tert-butoxyphenyl butyl 1774 methyl 2-tert-butoxyphenyl tert-butyl 1775 methyl 2-tert-butoxyphenyl hexyl 1776 methyl 2-tert-butoxyphenyl allyl 1777 methyl 2-tert-butoxyphenyl (E) -3-chloro-allyl 1778 methyl 2-tert-butoxyphenyl propynyl 1779 methyl 2-tert-butoxyphenyl 3-methyl-2-butenyl 1780 methyl 3-tert-butoxyphenyl H 1781 methyl 3-tert-butoxyphenyl methyl 1782 methyl 3-tert-butoxyphenyl ethyl 1783 methyl 3-tert-butoxyphenyl propyl 1784 methyl 3-tert-butoxyphenyl isopropyl 1785 methyl 3-tert-butoxyphenyl butyl 1786 methyl 3-tert-butoxyphenyl tert-butyl 1787 methyl 3-tert-butoxyphenyl hexyl 1788 methyl 3-tert-butoxyphenyl allyl 1789 methyl 3-tert-butoxyphenyl (E) -3-chloro-allyl 1790 methyl 3-tert-butoxyphenyl propynyl 1791 methyl 3-tert-butoxyphenyl 3-methyl-2-butenyl 1792 methyl 4-tert-butoxyphenyl H 1793 methyl 4-tert-butoxyphenyl methyl 1794 methyl 4-tert-butoxyphenyl ethyl 1795 methyl 4-tert-butoxyphenyl propyl

• ·

104

Song R ³ R ⁴ R ⁵ 1796 methyl 4-tert-butoxyphenyl isopropyl 1797 methyl 4-tert-butoxyphenyl butyl 1798 methyl 4-tert-butoxyphenyl tert-butyl 1799 methyl 4-tert-butoxyphenyl hexyl 1800 methyl 4-tert-butoxyphenyl allyl 1801 methyl 4-tert-butoxyphenyl (E) -3-chloro-allyl 1802 methyl 4-tert-butoxyphenyl propynyl 1803 methyl 4-tert-butoxyphenyl 3-methyl-2-butenyl 1804 methyl 2-CF ₃ -phenyl H 1805 methyl 2-CF ₃ -phenyl methyl 1806 methyl 2-CF ₃ -phenyl ethyl 1807 methyl 2-CF ₃ -phenyl propyl 1808 methyl 2-CF ₃ -phenyl isopropyl 1809 methyl 2-CF ₃ -phenyl butyl 1810 methyl 2-CF ₃ -phenyl tert-butyl 1811 methyl 2-CF ₃ -phenyl hexyl 1812 methyl 2-CF ₃ -phenyl allyl 1813 methyl 2-CF ₃ -phenyl (E) -3-chloro-allyl 1814 methyl 2-CF ₃ -phenyl propynyl 1815 methyl 2-CF ₃ -phenyl 3-methyl-2-butenyl 1816 methyl 3-CF ₃ -phenyl H 1817 methyl 3-CF ₃ -phenyl methyl 1818 methyl 3-CF ₃ -phenyl ethyl 1819 methyl 3-CF ₃ -phenyl propyl 1820 methyl 3-CF ₃ -phenyl isopropyl

105 • ·

Song R ³ R ⁴ R ⁵ 1821 methyl 3-CF ₃ -phenyl butyl 1822 methyl 3-CF ₃ -phenyl tert-butyl 1823 methyl 3-CF ₃ -phenyl hexyl 1824 methyl 3-CF ₃ -phenyl allyl 1825 methyl 3-CF ₃ -phenyl (E) -3-chloro-allyl 1826 methyl 3-CF ₃ -phenyl propynyl 1827 methyl 3-CF ₃ -phenyl 3-methyl-2-butenyl 1828 methyl 4-CF ₃ -phenyl H 1829 methyl 4-CF ₃ -phenyl methyl 1830 methyl 4-CF ₃ -phenyl ethyl 1831 methyl 4-CF ₃ -phenyl propyl 1832 methyl 4-CF ₃ -phenyl isopropyl 1833 methyl 4-CF ₃ -phenyl butyl 1834 methyl 4-CF ₃ -phenyl tert-butyl 1835 methyl 4-CF ₃ -phenyl hexyl 1836 methyl 4-CF ₃ -phenyl allyl 1837 methyl 4-CF ₃ -phenyl (E) -3-chloro-allyl 1838 methyl 4-CF ₃ -phenyl propynyl 1839 methyl 4-CF ₃ -phenyl 3-methyl-2-butenyl 1840 methyl 2-aminophenyl H 1841 methyl 2-aminophenyl methyl 1842 methyl 2-aminophenyl ethyl 1843 methyl 2-aminophenyl propyl 1844 methyl 2-aminophenyl isopropyl 1845 methyl 2-aminophenyl butyl

106 • · · · ·

Song R ³ R ⁴ R ⁵ 1846 methyl 2-aminophenyl tert-butyl 1847 methyl 2-aminophenyl hexyl 1848 methyl 2-aminophenyl allyl 1849 methyl 2-aminophenyl (E) -3-chloro-allí1 1850 methyl 2-aminophenyl propynyl 1851 methyl 2-aminophenyl 3-methyl-2-butenyl 1852 methyl 3-aminophenyl H 1853 methyl 3-aminophenyl methyl 1854 methyl 3-aminophenyl ethyl 1855 methyl 3-aminophenyl propyl 1856 methyl 3-aminophenyl isopropyl 1857 methyl 3-aminophenyl butyl 1858 methyl 3-aminophenyl tert-butyl 1859 methyl 3-aminophenyl hexyl 1860 methyl 3-aminophenyl allyl 1861 methyl 3-aminophenyl (E) -3-chloro-allyl 1862 methyl 3-aminophenyl propynyl 1863 methyl 3-aminophenyl 3-methyl-2-butenyl 1864 methyl 4-aminophenyl H 1865 methyl 4-aminophenyl methyl 1866 methyl 4-aminophenyl ethyl 1867 methyl 4-aminophenyl propyl 1868 methyl 4-aminophenyl isopropyl 1869 methyl 4-aminophenyl butyl 1870 methyl 4-aminophenyl tert-butyl

107

Song R ³ R ⁴ R ⁵ 1871 methyl 4-aminophenyl hexyl 1872 methyl 4-aminophenyl allyl 1873 methyl 4-aminophenyl (E) -3-chloro-allyl 1874 methyl 4-aminophenyl propynyl 1875 methyl 4-aminophenyl 3-methyl-2-butenyl 1876 methyl 2-N (CH ₃ ) ₂ -phenyl H 1877 methyl 2-N (CH ₃ ) ₂ -phenyl methyl 1878 methyl 2-N (CH ₃ ) ₂ -phenyl ethyl 1879 methyl 2-N (CH ₃ ) ₂ -phenyl propyl 1880 methyl 2-N (CH ₃ ) ₂ -phenyl isopropyl 1881 methyl 2-N (CH ₃ ) ₂ -phenyl butyl 1882 methyl 2-N (CH ₃ ) ₂ -phenyl tert-butyl 1883 methyl 2-N (CH ₃ ) ₂ -phenyl hexyl 1884 methyl 2-N (CH ₃ ) ₂ -phenyl allyl 1885 methyl 2-N (CH ₃ ) ₂ -phenyl (E) -3-chloro-allyl 1886 methyl 2-N (CH ₃ ) ₂ -phenyl propynyl 1887 methyl 2-N (CH ₃ ) ₂ -phenyl 3-methyl-2-butenyl 1888 methyl 3-N (CH ₃ ) ₂ -phenyl H 1889 methyl 3-N (CH ₃ ) ₂ -phenyl methyl 1890 methyl 3-N (CH ₃ ) ₂ -phenyl ethyl 1891 methyl 3-N (CH ₃ ) ₂ -phenyl propyl 1892 methyl 3-N (CH ₃ ) ₂ -phenyl isopropyl 1893 methyl 3-N (CH ₃ ) ₂ -phenyl butyl 1894 methyl 3-N (CH ₃ ) ₂ -phenyl tert-butyl 1895 methyl 3-N (CH ₃ ) ₂ -phenyl hexyl

• · • · · ·

108

Song R ³ R ⁴ R ⁵ 1896 methyl 3-N (CH ₃ ) ₂ -phenyl allyl 1897 methyl 3-N (CH ₃ ) ₂ -phenyl (E) -3-chloro-allyl 1898 methyl 3-N (CH ₃ ) ₂ -phenyl propynyl 1899 methyl 3-N (CH ₃ ) ₂ -phenyl 3-methyl-2-butenyl 1900 methyl 4-N (CH ₃ ) ₂ -phenyl H 1901 methyl 4-N (CH ₃ ) ₂ -phenyl methyl 1902 methyl 4-N (CH ₃ ) ₂ -phenyl ethyl 1903 methyl 4-N (CH ₃ ) ₂ -phenyl propyl 1904 methyl 4-N (CH ₃ ) ₂ -phenyl isopropyl 1905 methyl 4-N (CH ₃ ) ₂ -phenyl butyl 1906 methyl 4-N (CH ₃ ) ₂ -phenyl tert-butyl 1907 methyl 4-N (CH ₃ ) ₂ -phenyl hexyl 1908 methyl 4-N (CH ₃ ) ₂ -phenyl allyl 1909 methyl 4-N (CH ₃ ) ₂ -phenyl (E) -3-chloro-allyl 1910 methyl 4-N (CH ₃ ) 2-phenyl propynyl 1911 methyl 4-N (CH ₃ ) ₂ -phenyl 3-methyl-2-butenyl 1912 methyl 2-H ₂ NC (= S) -phenyl H 1913 methyl 2-H ₂ NC (= S) -phenyl methyl 1914 methyl 2-H ₂ NC (= S) -phenyl ethyl 1915 methyl 2-H ₂ NC (= S) -phenyl propyl 1916 methyl 2-H ₂ NC (= S) -phenyl isopropyl 1917 methyl 2-H ₂ NC (= S) -phenyl butyl 1918 methyl 2-H ₂ NC (= S) -phenyl tert-butyl 1919 methyl 2-H ₂ NC (= S) -phenyl hexyl 1920 methyl 2-H ₂ NC (= S) -phenyl allyl

109 β ·

Song R ³ R ⁴ R ⁵ 1921 methyl 2-H ₂ NC (= S) -phenyl (E) -3-chloro-allyl 1922 methyl 2-H ₂ NC (= S) -phenyl propynyl 1923 methyl 2-H ₂ NC (= S) -phenyl 3-methyl-2-butenyl 1924 methyl 3-H ₂ NC (= S) -phenyl H 1925 methyl 3-H ₂ NC (= S) -phenyl methyl 1926 methyl 3-H ₂ NC (= S) -phenyl ethyl 1927 methyl 3-H ₂ NC (= S) -phenyl propyl 1928 methyl 3-H ₂ NC (= S) -phenyl isopropyl 1929 methyl 3-H ₂ NC (= S) -phenyl butyl 1930 methyl 3-H ₂ NC (= S) -phenyl tert-butyl 1931 methyl 3-H ₂ NC (= S) -phenyl hexyl 1932 methyl 3-H ₂ NC (= S) -phenyl allyl 1933 methyl 3-H ₂ NC (= S) -phenyl (E) -3-chloro-allyl 1934 methyl 3-H ₂ NC (= S) -phenyl propynyl 1935 methyl 3-H ₂ NC (= S) -phenyl 3-methyl-2-butenyl 1936 methyl 4-H ₂ NC (= S) -phenyl H 1937 methyl 4-H ₂ NC (= S) -phenyl methyl 1938 methyl 4-H ₂ NC (= S) -phenyl ethyl 1939 methyl 4-H ₂ NC (= S) -phenyl propyl 1940 methyl 4-H ₂ NC (= S) -phenyl isopropyl 1941 methyl 4-H ₂ NC (= S) -phenyl butyl 1942 methyl 4-H ₂ NC (= S) -phenyl tert-butyl 1943 methyl 4-H ₂ NC (= S) -phenyl hexyl 1944 methyl 4-H ₂ NC (= S) -phenyl allyl 1945 methyl 4-H ₂ NC (= S) -phenyl (E) -3-chloro-allyl

110

Song R ³ R ⁴ R ⁵ 1946 methyl 4-H.NC (= S) -phenyl propynyl 1947 methyl 4-H ₂ NC (= S) -phenyl 3-methyl-2-butenyl 1948 methyl 2-CF ₃ O-phenyl H 1949 methyl 2-CF ₃ O-phenyl methyl 1950 methyl 2-CF ₃ O-phenyl ethyl 1951 methyl 2-CF ₃ Of enil propyl 1952 methyl 2-CF ₃ Of enil isopropyl 1953 methyl 2-CF ₃ O-phenyl butyl 1954 methyl 2-CF ₃ O-phenyl tert-butyl 1955 methyl 2-CF ₃ Of enil hexyl 1956 methyl 2-CF ₃ O-phenyl allyl 1957 methyl 2-CF ₃ O-phenyl (E) -3-chloro-allyl 1958 methyl 2-CF ₃ O-phenyl propynyl 1959 methyl 2-CF ₃ O-phenyl 3-methyl-2-butenyl 1960 methyl 3-CF ₃ O-phenyl H 1961 methyl 3-CF ₃ O-phenyl methyl 1962 methyl 3-CF ₃ O-phenyl ethyl 1963 methyl 3-CF ₃ O-phenyl propyl 1964 methyl 3-CF ₃ Of enil isopropyl 1965 methyl 3-CF ₃ O-phenyl butyl 1966 methyl 3-CF ₃ Of enil tert-butyl 1967 methyl 3-CF ₃ O-phenyl hexyl 1968 methyl 3-CF ₃ O-phenyl allyl 1969 methyl 3-CF ₃ O-phenyl (E) -3-chloro-allyl 1970 methyl 3-CF ₃ Of enil propynyl

111

Song R ³ R ⁴ R ⁵ 1971 methyl 3-CF ₃ Of enil 3-methyl-2-butenyl 1972 methyl 4-CF ₃ Of enil H 1973 methyl 4-CF ₃ O-phenyl methyl 1974 methyl 4-CF ₃ O-phenyl ethyl 1975 methyl 4-CF ₃ O-phenyl propyl 1976 methyl 4-CF ₃ O-phenyl isopropyl 1977 methyl 4-CF ₃ O-phenyl butyl 1978 methyl 4-CF ₃ O-phenyl tert-butyl 1979 methyl 4-CF ₃ O-phenyl hexyl 1980 methyl 4-CF ₃ O-phenyl allyl 1981 methyl 4-CF ₃ O-phenyl (E) -3-chloro-allyl 1982 methyl 4-CF ₃ O-phenyl propynyl 1983 methyl 4-CF ₃ O-phenyl 3-methyl-2-butenyl 1984 methyl 2- (methylthio) phenyl H 1985 methyl 2- (methylthio) phenyl methyl 1986 methyl 2- (methylthio) phenyl ethyl 1987 methyl 2- (methylthio) phenyl propyl 1988 methyl 2- (methylthio) phenyl isopropyl 1989 methyl 2- (methylthio) phenyl butyl 1990 methyl 2- (methylthio) phenyl tert-butyl 1991 methyl 2- (methylthio) phenyl hexyl 1992 methyl 2- (methylthio) phenyl allyl 1993 methyl 2- (methylthio) phenyl (E) -3-chloro-allyl 1994 methyl 2- (methylthio) phenyl propynyl 1995 methyl 2- (methylthio) phenyl 3-methyl-2-butenyl

112

Song R ³ R ⁴ R ⁵ 1996 methyl 3- (methylthio) phenyl H 1997 methyl 3- (methylthio) phenyl methyl 1998 methyl 3- (methylthio) phenyl ethyl 1999 methyl 3- (methylthio) phenyl propyl 2000 methyl 3- (methylthio) phenyl isopropyl 2001 methyl 3- (methylthio) phenyl butyl 2002 methyl 3- (methylthio) phenyl tert-butyl 2003 methyl 3- (methylthio) phenyl hexyl 2004 methyl 3- (methylthio) phenyl allyl 2005 methyl 3- (methylthio) phenyl (E) -3-chloro-allyl 2006 methyl 3- (methylthio) phenyl propynyl 2007 methyl 3- (methylthio) phenyl 3-butenyl meti1-2 2008 methyl 4- (methylthio) phenyl H 2009 methyl 4- (methylthio) phenyl methyl 2010 methyl 4- (methylthio) phenyl ethyl 2011 methyl 4- (methylthio) phenyl propyl 2012 methyl 4- (methylthio) phenyl isopropyl 2013 methyl 4- (methylthio) phenyl butyl 2014 methyl 4- (methylthio) phenyl tert-butyl 2015 methyl 4- (methylthio) phenyl hexyl 2016 methyl 4- (methylthio) phenyl allyl 2017 methyl 4- (methylthio) phenyl (E) -3-chloro-allyl 2018 methyl 4- (methylthio) phenyl propynyl 2019 methyl 4- (methylthio) phenyl 3-methyl-2-butenyl 2020 methyl 2-CH ₃ SO ₂ -phenyl H

«·

113

Song R ³ R ⁴ R ⁵ 2021 methyl 2-CH ₃ SO ₂ -phenyl methyl 2022 methyl 2-CH ₃ SO ₂ -phenyl ethyl 2023 methyl 2-CH ₃ SO ₂ -phenyl propyl 2024 methyl 2-CH ₃ SO ₂ -phenyl isopropyl 2025 methyl 2-CH ₃ SO ₂ -phenyl butyl 2026 methyl 2-CH ₃ SO ₂ -phenyl tert-butyl 2027 methyl 2-CH ₃ SO ₂ -phenyl hexyl 2028 methyl 2-CH ₃ SO ₂ -phenyl allyl 2029 methyl 2-CH ₃ SO ₂ -phenyl (E) -3-chloro-allyl 2030 methyl 2-CH ₃ SO ₂ -phenyl propynyl 2031 methyl 2-CH ₃ SO ₂ -phenyl 3-meti1-2 buteni1 2032 methyl 3-CH ₃ SO ₂ -phenyl H 2033 methyl 3-CH ₃ SO ₂ -phenyl methyl 2034 methyl 3-CH ₃ SO ₂ -phenyl ethyl 2035 methyl 3-CH ₃ SO ₂ -phenyl propyl 2036 methyl 3-CH ₃ SO ₂ -phenyl isopropyl 2037 methyl 3-CH ₃ SO ₂ -phenyl butyl 2038 methyl 3-CH ₃ SO ₂ -phenyl tert-butyl 2039 methyl 3-CH ₃ SO ₂ -phenyl hexyl 2040 methyl 3-CH ₃ SO ₂ -phenyl allyl 2041 methyl 3-CH ₃ SO ₂ -phenyl (E) -3-chloro-allyl 2042 methyl 3-CH ₃ SO ₂ -phenyl propynyl 2043 methyl 3-CH ₃ SO ₂ -phenyl 3-methyl-2-butenyl 2044 methyl 4-CH ₃ SO ₂ -phenyl H 2045 methyl 4-CH ₃ SO ₂ -phenyl methyl

• ·

114

Song R ³ R ⁴ R ⁵ 2046 methyl 4-CH ₃ SO ₂ -phenyl ethyl 2047 methyl 4-CH ₃ SO ₂ -phenyl propyl 2048 methyl 4-CH ₃ SO ₂ -phenyl isopropyl 2049 methyl 4-CH ₃ SO ₂ -phenyl butyl 2050 methyl 4-CH ₃ SO ₂ -phenyl tert-butyl 2051 methyl 4-CH ₃ SO ₂ -phenyl hexyl 2052 methyl 4-CH ₃ SO ₂ -phenyl allyl 2053 methyl 4-CH ₃ SO ₂ -phenyl (E) -3-chloro-allyl 2054 methyl 4-CH ₃ SO ₂ -phenyl propynyl 2055 methyl 4-CH ₃ SO ₂ -phenyl 3-methyl-2-butenyl 2056 methyl 2-CH ₃ OC (= O) -phenyl H 2057 methyl 2-CH ₃ OC (= O) -phenyl methyl 2058 methyl 2-CH3OC (= O) -phenyl ethyl 2059 methyl 2-CH ₃ OC (= O) -phenyl propyl 2060 methyl 2-CH ₃ OC (= O) -phenyl isopropyl 2061 methyl 2-CH3OC (= O) -phenyl butyl 2062 methyl 2-CH ₃ OC (= O) -phenyl tert-butyl 2063 methyl 2-CH ₃ OC (= O) -phenyl hexyl 2064 methyl 2-CH ₃ OC (= O) -phenyl allyl 2065 methyl 2-CH ₃ OC (= O) -phenyl (E) -3-chloro-allyl 2066 methyl 2-CH ₃ OC (= O) -phenyl propynyl 2067 methyl 2-CH ₃ OC (= O) -phenyl 3-methyl-2-butenyl 2068 methyl 3-CH3OC (= O) -phenyl H 2069 methyl 3-CH ₃ OC (= O) -phenyl methyl 2070 methyl 3-CH ₃ OC (= O) -phenyl ethyl

• · · · ·

115

Song R ³ R ⁴ R ⁵ 2071 methyl 3-CH ₃ OC (= O) -phenyl propyl 2072 methyl 3-CH ₃ OC (= O) -phenyl isopropyl 2073 methyl 3-CH ₃ OC (= O) -phenyl butyl 2074 methyl 3-CH ₃ OC (= O) -phenyl tert-butyl 2075 methyl 3-CH ₃ OC (= O) -phenyl hexyl 2076 methyl 3-CH ₃ OC (= O) -phenyl allyl 2077 methyl 3-CH ₃ OC (= O) -phenyl (E) -3-chloro-allyl 2078 methyl 3-CH ₃ OC (= O) -phenyl propynyl 2079 methyl 3-CH 3 OC (= 0) -phenyl 3-methyl-2-butenyl 2080 methyl 4-CH ₃ OC (= O) -phenyl H 2081 methyl 4-CH ₃ OC (= O) -phenyl methyl 2082 methyl 4-CH ₃ OC (= O) -phenyl ethyl 2083 methyl 4-CH ₃ OC (= O) -phenyl propyl 2084 methyl 4-CH ₃ OC (= O) -phenyl isopropyl 2085 methyl 4-CH ₃ OC (= O) -phenyl butyl 2086 methyl 4-CH ₃ OC (= O) -phenyl tert-butyl 2087 methyl 4-CH ₃ OC (= O) -phenyl hexyl 2088 methyl 4-CH ₃ OC (= O) -phenyl allyl 2089 methyl 4-CH ₃ OC (= O) -phenyl (E) -3-chloro-allyl 2090 methyl 4-CH ₃ OC (= O) -phenyl propynyl 2091 methyl 4-CH ₃ OC (= O) -phenyl 3-methyl-2-butenyl 2092 methyl 2-C ₂ H ₅ OC (= O) -phenyl H 2093 methyl 2-C ₂ H ₅ OC (= O) -phenyl methyl 2094 methyl 2-C ₂ H ₅ OC (= O) -phenyl ethyl 2095 methyl 2-C ₂ H ₅ OC (= O) -phenyl propyl

• · ·· «

116

Song R ³ R ⁴ R ⁵ 2096 methyl 2-C ₂ H ₅ OC (= O) -phenyl isopropyl 2097 methyl 2-C, H ₅ OC (= O) -phenyl butyl 2098 methyl 2-C ₂ H ₅ OC (= O) -phenyl tert-butyl 2099 methyl 2-C ₂ H ₅ OC (= O) -phenyl hexyl 2100 methyl 2-C ₂ H ₅ OC (= O) -phenyl allyl 2101 methyl 2-C ₂ H ₅ OC (= O) -phenyl (E) -3-chloro-allyl 2102 methyl 2-C ₂ H ₅ OC (= O) -phenyl propynyl 2103 methyl 2-C ₂ H ₅ OC (= O) -phenyl 3-methyl-2-butenyl 2104 methyl 3-C ₂ H ₅ OC (= O) -phenyl H 2105 methyl 3-C ₂ H ₅ OC (= O) -phenyl methyl 2106 methyl 3-C ₂ H ₅ OC (= O) -phenyl ethyl 2107 methyl 3-C ₂ H ₅ OC (= O) -phenyl propyl 2108 methyl 3-C ₂ H ₅ OC (= O) -phenyl isopropyl 2109 methyl 3-C ₂ H ₅ OC (= O) -phenyl butyl 2110 methyl 3-C ₂ H ₅ OC (= O) -phenyl tert-butyl 2111 methyl 3-C ₂ H ₅ OC (= O) -phenyl hexyl 2112 methyl 3-C ₂ H ₅ OC (= O) -phenyl allyl 2113 methyl 3-C ₂ H ₅ OC (= O) -phenyl (E) -3-chloro-allyl 2114 methyl 3-C ₂ H ₅ OC (= O) -phenyl propynyl 2115 methyl 3-C ₂ H ₅ OC (= O) -phenyl 3-methyl-2-butenyl 2116 methyl 4-C ₂ H ₅ OC (= O) -phenyl H 2117 methyl 4-C ₂ H ₅ OC (= O) -phenyl methyl 2118 methyl 4-C ₂ H ₅ OC (= O) -phenyl ethyl 2119 methyl 4-C ₂ H ₅ OC (= O) -phenyl propyl 2120 methyl 4-C ₂ H ₅ OC (= O) -phenyl isopropyl

··· »·

117

Song R ³ R ⁴ R ⁵ 2121 methyl 4-C ₂ H ₅ OC (= O) -phenyl butyl 2122 methyl 4-C ₂ H ₅ OC (= O) -phenyl tert-butyl 2123 methyl 4-C ₂ H ₅ OC (= O) -phenyl hexyl 2124 methyl 4-C ₂ H ₅ OC (= O) -phenyl allyl 2125 methyl 4-C ₂ H ₅ OC (= O) -phenyl (E) -3-chloro-allyl 2126 methyl 4-C ₂ H ₅ OC (= O) -phenyl propynyl 2127 methyl 4-C ₂ H ₅ OC (= O) -phenyl 3-methyl-2-butenyl 2128 methyl 2-carboxyphenyl H 2129 methyl 2-carboxyphenyl methyl 2130 methyl 2-carboxyphenyl ethyl 2131 methyl 2-carboxyphenyl propyl 2132 methyl 2-carboxyphenyl isopropyl 2133 methyl 2-carboxyphenyl butyl 2134 methyl 2-carboxyphenyl tert-butyl 2135 methyl 2-carboxyphenyl hexyl 2136 methyl 2-carboxyphenyl allyl 2137 methyl 2-carboxyphenyl (E) -3-chloro-allyl 2138 methyl 2-carboxyphenyl propynyl 2139 methyl 2-carboxyphenyl 3-methyl-2-butenyl 2140 methyl 3-carboxyphenyl H 2141 methyl 3-carboxyphenyl methyl 2142 methyl 3-carboxyphenyl ethyl 2143 methyl 3-carboxyphenyl propyl 2144 methyl 3-carboxyphenyl isopropyl 2145 methyl 3-carboxyphenyl butyl

118

Song R ³ R ⁴ R ⁵ 2146 methyl 3-carboxyphenyl tert-butyl 2147 methyl 3-carboxyphenyl hexyl 2148 methyl 3-carboxyphenyl allyl 2149 methyl 3-carboxyphenyl (E) -3-chloro-allyl 2150 methyl 3-carboxyphenyl propynyl 2151 methyl 3-carboxyphenyl 3-methyl-2-butenyl 2152 methyl 4-carboxyphenyl H 2153 methyl 4-carboxyphenyl methyl 2154 methyl 4-carboxyphenyl ethyl 2155 methyl 4-carboxyphenyl propyl 2156 methyl 4-carboxyphenyl isopropyl 2157 methyl 4-carboxyphenyl butyl 2158 methyl 4-carboxyphenyl tert-butyl 2159 methyl 4-carboxyphenyl hexyl 2160 methyl 4-carboxyphenyl allyl 2161 methyl 4-carboxyphenyl (E) -3-chloro-allyl 2162 methyl 4-carboxyphenyl propynyl 2163 methyl 4-carboxyphenyl 3-methyl-2-butenyl 2164 methyl 2-HN (CH ₃ ) C (= O) -phenyl H 2165 methyl 2-HN (CH ₃ ) C (= O) -phenyl methyl 2166 methyl 2-HN (CH ₃ ) C (= O) -phenyl ethyl 2167 methyl 2-HN (CH ₃ ) C (= O) -phenyl propyl 2168 methyl 2-HN (CH ₃ ) C (= O) -phenyl isopropyl 2169 methyl 2-HN (CH ₃ ) C (= O) -phenyl butyl 2170 methyl 2-HN (CH ₃ ) C (= O) -phenyl tert-butyl

119

Song R ³ R ⁴ R ⁵ 2171 methyl 2-HN (CH ₃ ) C (= O) -phenyl hexyl 2172 methyl 2-HN (CH ₃ ) C (= O) -phenyl allyl 2173 methyl 2-HN (CH ₃ ) C (= O) -phenyl (E) -3-chloro-allyl 2174 methyl 2-HN (CH ₃ ) C (= O) -phenyl propynyl 2175 methyl 2-HN (CH ₃ ) C (= O) -phenyl 3-methyl-2-hűteni1 2176 methyl 3-HN (CH ₃ ) C (= O) -phenyl H 2177 methyl 3-HN (CH ₃ ) C (= O) -phenyl methyl 2178 methyl 3-HN (CH ₃ ) C (= O) -phenyl ethyl 2179 methyl 3-HN (CH ₃ ) C (= O) -phenyl propyl 2180 methyl 3-HN (CH ₃ ) C (= O) -phenyl isopropyl 2181 methyl 3-HN (CH ₃ ) C (= O) -phenyl butyl 2182 methyl 3-HN (CH ₃ ) C (= O) -phenyl tert-butyl 2183 methyl 3-HN (CH ₃ ) C (= O) -phenyl hexyl 2184 methyl 3-HN (CH ₃ ) C (= O) -phenyl allyl 2185 methyl 3-HN (CH ₃ ) C (= O) -phenyl (E) -3-chloro-allyl 2186 methyl 3-HN (CH ₃ ) C (= O) -phenyl propynyl 2187 methyl 3-HN (CH ₃ ) C (= O) -phenyl 3-methyl-2-butenyl 2188 methyl 4-HN (CH ₃ ) C (= O) -phenyl H 2189 methyl 4-HN (CH ₃ ) C (= O) -phenyl methyl 2190 methyl 4-HN (CH ₃ ) C (= O) -phenyl ethyl 2191 methyl 4-HN (CH ₃ ) C (= O) -phenyl propyl 2192 methyl 4-HN (CH ₃ ) C (= O) -phenyl isopropyl 2193 methyl 4-HN (CH ₃ ) C (= O) -phenyl butyl 2194 methyl 4-HN (CH ₃ ) C (= O) -phenyl tert-butyl 2195 methyl 4-HN (CH ₃ ) C (= O) -phenyl hexyl

120 • · · · * • · · · · · · · · · · · · · · ·

Song R ³ R ⁴ R ⁵ 2196 methyl 4-HN (CH ₃ ) C (= O) -phenyl allyl 2197 methyl 4-HN (CH ₃ ) C (= O) -phenyl (E) -3-chloro-allyl 2198 methyl 4-HN (CH ₃ ) C (= O) -phenyl propynyl 2199 methyl 4-HN (CH ₃ ) C (= O) -phenyl 3-methyl-2-butenyl 2200 methyl 2-N (CH ₃ ) ₂ C (= O) -phenyl H 2201 methyl 2-N (CH ₃ ) ₂ C (= O) -phenyl methyl 2202 methyl 2-N (CH ₃ ) ₂ C (= O) -phenyl ethyl 2203 methyl 2-N (CH ₃ ) ₂ C (= O) -phenyl propyl 2204 methyl 2-N (CH ₃ ) ₂ C (= O) -phenyl isopropyl 2205 methyl 2-N (CH ₃ ) ₂ C (= O) -phenyl butyl 2206 methyl 2-N (CH ₃ ) ₂ C (= O) -phenyl tert-butyl 2207 methyl 2-N (CH ₃ ) ₂ C (= O) -phenyl hexyl 2208 methyl 2-N (CH ₃ ) ₂ C (= O) -phenyl allyl 2209 methyl 2-N (CH ₃ ) ₂ C (= O) -phenyl (E) -3-chloro-allyl 2210 methyl 2-N (CH ₃ ) ₂ C (= O) -phenyl propynyl 2211 methyl 2-N (CH ₃ ) ₂ C (= O) -phenyl 3-methyl-2-butenyl 2212 methyl 3-N (CH ₃ ) ₂ C (= O) -phenyl H 2213 methyl 3-N (CH ₃ ) ₂ C (= O) -phenyl methyl 2214 methyl 3-N (CH ₃ ) ₂ C (= O) -phenyl ethyl 2215 methyl 3-N (CH ₃ ) ₂ C (= O) -phenyl propyl 2216 methyl 3-N (CH ₃ ) ₂ C (= O) -phenyl isopropyl 2217 methyl 3-N (CH ₃ ) ₂ C (= O) -phenyl butyl 2218 methyl 3-N (CH ₃ ) ₂ C (= O) -phenyl tert-butyl 2219 methyl 3-N (CH ₃ ) ₂ C (= O) -phenyl hexyl 2220 methyl 3-N (CH ₃ ) ₂ C (= O) -phenyl allyl

• «· · • · · · · ·

121 • ·

Song R ³ R ⁴ R ⁵ 2221 methyl 3-N (CH ₃ ) ₂ C (= O) -phenyl (E) -3-chloro-allyl 2222 methyl 3-N (CH ₃ ) ₂ C (= O) -phenyl propynyl 2223 methyl 3-N (CH ₃ ) ₂ C (= O) -phenyl 3-butenyl meti1-2 2224 methyl 4-N (CH ₃ ) ₂ C (= O) -phenyl H 2225 methyl 4-N (CH ₃ ) ₂ C (= O) -phenyl methyl 2226 methyl 4-N (CH ₃ ) ₂ C (= O) -phenyl ethyl 2227 methyl 4-N (CH ₃ ) ₂ C (= O) -phenyl propyl 2228 methyl 4-N (CH ₃ ) ₂ C (= O) -phenyl isopropyl 2229 methyl 4-N (CH ₃ ) ₂ C (= O) -phenyl butyl 2230 methyl 4-N (CH ₃ ) ₂ C (-O) -phenyl tert-butyl 2231 methyl 4-N (CH ₃ ) ₂ C (= O) -phenyl hexyl 2232 methyl 4-N (CH ₃ ) ₂ C (= O) -phenyl allyl 2233 methyl 4-N (CH ₃ ) ₂ C (= O) -phenyl (E) -3-chloro-allyl 2234 methyl 4-N (CH ₃ ) ₂ C (= O) -phenyl propynyl 2235 methyl 4-N (CH ₃ ) ₂ C (= O) -phenyl 3-methyl-2-butenyl

The compounds of formula I are useful as active ingredients in fungicidal compositions.

The compounds of formula (I) exhibit excellent activity against a broad spectrum of phytopathogenic fungi, especially those of the class Ascomycetes and Basidiomycetes. They act partially systemically and can be used as active ingredients in foliar and soil fungicides.

It is particularly important to combat many fungal species that damage various crops and their seeds; such a crop • ·

Examples include wheat, rye, barley, oats, rice, corn, turf, cotton, soy, coffee, sugar cane, grapes, fruits, ornamental plants and vegetables such as cucumbers. , beans and pumpkin.

The novel compounds of the present invention are particularly useful for controlling the following fungal pests:

Erysiphe graminis on cereals,

Erysiphe cichoracearum and Sphaerotheca fuliginae on pumpkin,

Podosphera leucotricha, the apple,

Uncinula necator on the vine,

Puccinia species on cereals,

Rhizoctonia species on cotton and lawn,

Cauliflower species on cereals and sugar cane,

Venturia inaequalis, the apple,

Helminthosporium species on cereals,

Septoria nodorum on wheat,

Botrytis cinerea, on strawberries and on grapes,

Cercospora arachidicola on peanuts,

Pseudocercosporella herpotrichoides, wheat and barley,

Pyricularia oryzae, on rice,

Phytophthera infestans, on potatoes and tomatoes,

Fusarium and Verticillium species on different plants,

Plasmopara viticola on the vine,

Alternaria species on vegetables and fruits.

The novel compounds of the present invention are applied in a manner that provides effective control of the fungi or the material, seed, crop or soil to be protected against fungal infections.

123. The active compounds may be applied before or after the fungi are contaminated with the materials, crops or seeds.

The compounds of formula (I) may be incorporated into conventional formulations such as solutions, emulsions, suspensions, powders, pastes and granules. The application forms are adapted to the purpose of use; they must in all cases ensure a fine and uniform distribution of the active compounds of the invention. The formulations are prepared in a known manner, for example by diluting the active compounds with solvents and / or carriers, optionally employing emulsifiers and dispersants, and, if water is used as a diluent, other organic solvents may be used. Suitable excipients are essentially: solvents such as aromatic compounds (e.g. xylene), chlorinated aromatic compounds (e.g. chlorobenzene), paraffins (e.g. mineral oil fractions), alcohols (e.g. methanol or butanol), ketones (e.g. cyclohexanone), amines (e.g. ethanolamine), dimethylformamide and water; carriers such as natural rock flour (e.g. kaolin, clay, talc and chalk) and synthetic stone powders (e.g., highly dispersed silica, silicates); emulsifiers, such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl and aryl sulfonates); and dispersants, such as lignin sulfite impurities and methyl cellulose.

Fungicidal compositions are generally 0.1 to 95, preferably 0.5 to 90

They contain 9% by weight of the active ingredient.

The amount used depends on the type of effect desired

Value between 0.01 and 2.0 kg active ingredient / ha.

Generally, from 0.001 to 0.1 g, preferably 0.01 to 0.05 g of active ingredient per kg of seed is sufficient for seed treatment.

The active compounds according to the invention, as fungicides, can be combined with many other active ingredients, for example herbicides, insecticides, plant growth regulators, other fungicides or even fertilizers.

In many cases, the fungicidal spectrum of action is widened when mixed with other antifungal agents.

The following list of fungicidal agents that can be mixed with and co-administered with the active compounds of the present invention is given by way of example, but is not limited to the following examples:

sulfur;

dithiocarbamates and their derivatives such as ferricdimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bis (dithiocarbamate), manganese ethylene bis (dithiocarbamate), manganese zinc ethylene diamine bis (dithiocarbamate), disulfides, zinc N, Ν '-ethylene bis (dithiocarbamate) ammonia complex, zinc N, N' -propylene bis (dithiocarbamate) ammonia complex, zinc Ν, Ν '-propylene bis (dithiocarbamate) .

N, N'-polypropylene bis (thiocarbamoyl) disulfide;

125 «· nitro compounds such as dinitro (1-methylheptyl) phenyl crotonate,

2- (sec-butyl) -4,6-dinitro-phenyl-3,3-dimethyl-acrylate,

2- (sec-butyl) -4,6-dinitrophenyl isopropyl carbonate,

5-nitro-isophthalic acid diisopropyl and ester;

heterocyclic compounds such as

2-heptadecyl-2-imidazoline acetate,

2,4-dichloro-6- (o-chloroanilino) -s-triazine,

0, O-diethyl-phthalimido foszfonotioát,

5-amino-1- (bis (dimethylamino) phosphinyl) -3-phenyl-1,2,4-triazole,

2.3-diciano-1,4-dithio-anthraquinone,

2-thio-1,3-dithiol [4,5-b] quinoxaline,

Methyl 1- (butylcarbamoyl) -2-benzimidazole-carbamic acid,

2- (methoxycarbonylamino) -benzimidazole,

2- (2-furyl) -benzimidazole

2- (4-thiazolyl) benzimidazole,

N- (1,1,2,2-tetrachloro-ethylthio) -tetrahydrophthalimide,

N- (trichloromethyl-thio) -tetrahydrophthalimide,

N- (trichloromethyl-thio) phthalimide,

N- (dichlorofluoromethylthio) -Ν ', N' -dimethyl-N-phenyl-sulfuric acid diamide,

5-ethoxy-3- (trichloromethyl) -1,2,3-thiadiazole,

2- (thiocyanato-methylthio) benzothiazole,

1.4-dichloro-2,5-dimethoxybenzene,

4- (2-chlorophenylhydrazino) -3-methyl-5-isoxazolone, pyridine-2-thio-1-oxide,

8-hydroxyquinoline or copper salt,

2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxatin, · ·

126

2,3-dihydro-5-carboxanilido-6-methyl-l, 4-oxathiin-4,4-dioxide,

2-methyl-5,6-dihydro-4H-pyran-3-carboxylic acid anilide,

2-methylfuran-3-carboxylic acid anilide,

2,5-dimethyl-furan-3-carboxylic acid anilide,

2.4.5-Trimethyl-furan-3-carboxylic acid anilide,

2,5-Dimethyl-furan-3-carboxylic acid cyclohexylamide,

N-cyclohexyl-N-methoxy-2,5-dimethyl-furan-3-carboxylic acid amide,

2-methyl-benzoic acid anilide,

2-iodo-benzoic anilide,

N-formyl-N-morpholino-2,2,2-trichloroethyl acetal, piperazine-1,4-diylbis (1- (2,2,2-trichloroethyl) formamide),

1- (3,4-dichloro-phenylamino) -1- (forrni1-amino) -2,2,2-trichloroethane,

2,6-dimethyl-N-tridecylmorpholine and its salts,

2,6-dimethyl-N-cyclododecylmorpholine and 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-propyl-1,3-dioxolan-2-yl-ethyl] -1H-1,2,4-triazole,

N-propyl-N- (2,4,6-trichlorophenoxyethyl) -N'-imidazolylurea,

1- (4-chlorophenoxy) -3,3-dimethyl-l- (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-pyrimidine-methanol,

127

5-butyl-2- (dimethylamino) -4-hydroxy-6-methylpyrimidine, bis (p-chlorophenyl) -3-pyridine methanol,

1,2-bis (3-ethoxycarbonyl-2-thioureido) benzene,

1,2-bis z (3-methoxycarbonyl-2-thioureido) benzene;

and various fungicidal agents such as dodecylguanidine acetate,

3- [3- (3,5-Dimethyl-2-hydroxycyclohexyl) -2-hydroxyethyl] -glutarimide, hexachlorobenzene,

D, L-methyl-N- (2, β-dimethyl-phenyl) -N- (2-furoyl) alanine,

D, L-N- (2, β-dimethyl-phenyl) -N- (2-methoxyacetyl) alanine methyl ester,

N- (2, β-dimethyl-phenyl) -N- (chloroacetyl) -D, L-2-amino-butyrolactone,

D, L-N- (2, β-dimethylphenyl) -N- (phenylacetyl) alanine methyl ester,

5-methyl-5-vinyl-3- (3,5-dichlorophenyl) -2,4-dioxo-l, 3-oxazolidine

3- (3,5-dichlorophenyl) -5-methyl-5- (methoxymethyl) -1,3-oxazolidine-2,4-dione,

3- (3,5-dichlorophenyl) -1- (isopropylcarbamoyl) hydantoin,

N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-l, 2-dicarboximide,

2-cyano [N- (ethylaminocarbonyl) -2- (methoxyimino) acetamide,

1- [2- (2,4-Dichlorophenyl) pentyl) -1H-1,2,4-triazole,

2,4-difluoro-a- (1H-1,2,4-triazol-l-ylmethyl) -benzhidrilalkohol,

N- [3-chloro-2,6-dinitro-4- (trifluoromethyl) phenyl] -5- (trifluoromethyl) -3-chloro-2-aminopyridine,

1 - [(bis (4-fluorophenyl) methylsilyl) methyl] -1H-1,2,4-triazole.

The compounds of formula (I) are also suitable for application in the class of insects, arachnids and nematodes.

128 to combat smugglers; Thus, these compounds can be used as pesticides in plant protection as well as in hygiene, stock preservation and veterinary medicine.

Examples of pest insects of the order Lepidoptera include: Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Chua reticulana, Chua reticulana , Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiquella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholita funebrana, Grapholita funebrana, Grapholita undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keifferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithccolletis blancardella, Lobesia botrana, Lobesia botrana, Lobesia botrana ia, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flamea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scarbra, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia

129 ni, Zeirapnera 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 linear, Blastophagus piniperda, Blitophaga undata, Bruchus rufus

Byctiscus betlulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhyncus assimilis, Ceuthorrhyncus daily, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longica, Diabrotica 12-punctata, Diabrotica, Diabrotica 12-punctata Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Onlema oryzae, Ortiza

Ortiorrhynchus onus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus, Sitophilus granaria;

from the order Diptera, for example, Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia soghicola, brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossia morsitans, Haematobia irritans, Haplodiplosis • · ·

130 equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina,

Lucilia sericata, Lycoria pectoralis, Mayetiola destructor,

Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyani, Phorbia antiqua, Phorbia brassicae,

Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella,

Tabanus bovinus, Tipula oleracea, Tipula paludosa;

of the order Thysanoptera include, for example, Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci;

for example, of the order Hymenoptera:

Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana,

Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta;

from the order of the Heteroptera, for example, Arcosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euchistus impictiventris, Leptoglossus phyllopus, Lygus linadisis, Lygus pratensis perditor;

from the order Homoptera, for example, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Cerosipha gossypii, fabae, Macrosiphum avenae, Macrosiphum euphorbiae,

131

Macrosiphon rosae, Megoura viciae, Metopoiophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalomyzus ascalonicus,

Schizoneura lanuginosa, Trialeurodes vaporariorum, Viteus vitif ο 11 i;

from the order of termites (Isoptera), for example, Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus, Termes natalensis;

from the order of the orthoptera (Orthoptera), for example:

Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria,

Melanoplus bivittatus, Melanoplus femur rubrum, Melanoplus mexicanus, Melanoplus sanquinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana,

Schistocerca peregrina, Stauronotus maroccanus, Tachycines asynamorus;

from the arachnid class, for example, mites (Acaridae) 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, Permanyssus gallinae, Phyllocaptrata oleivora, Polyphagotarsonemus latus, Psoroptes ovis,

Rhipicephalus appendiculatus, Rhipicephalus evertsi, Saccoptes • ·

132 scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius, Tetranychus urticae; from the class of nematodes, for example, rootworm such as Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst nematodes such as Globodera rostochiensis, Heterodera avenae, Heterodera glycinae, Heterodera a, Heterodera scha 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 may be applied as such or in the form of their preparations or in ready-to-use forms, for example, directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprays or granules, by spraying, spraying, watering. The forms of application are fully adapted to the purpose for which they are intended; they must in all cases ensure as uniform a distribution as possible of the active substances according to the invention.

Concentrations of the active compounds in immediate-release formulations may vary within wide limits; their value is generally between 0.0001 and 10%, but preferably between 0.01 and 1%.

The active ingredients can be successfully applied in the ultra-small volume.

133 (ULV = ultra low volume) in which it is possible to dispense the active ingredient itself into a formulation containing more than 95% by weight of the active ingredient or even without the addition of additives.

The amount of active ingredient used to control pests in open fields is 0.1 to 2.0 kg / ha, preferably 0.2 to 1.0 kg / ha.

Medium to high boiling petroleum fractions such as kerosene or diesel oil, as well as coal tar oils and vegetable or animal oils, aliphatic, cyclic and aromatic hydrocarbons such as benzene, , alkylated naphthalenes or derivatives thereof, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, highly polar solvents such as dimethylformamide, dimethylsulfoxide, N-methyl water.

Aqueous formulations may be prepared from emulsion concentrates, pastes, wettable powders or oil dispersions by the addition of water. For the preparation of emulsions, pastes or oil dispersions, the active compounds, either alone or in an oil or solvent, may be homogenized in water with the aid of wetting, tackifying, dispersing or emulsifying agents. However, water-dilutable concentrates may also be prepared which may be prepared from the active ingredient, a wetting agent, a tackifier, a dispersant or emulsifier, and optionally a solvent or solvent.

They consist of 134 oils.

Surfactants include alkali metal, alkaline earth metal and ammonium salts of lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, alkyl aryl sulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohols and fatty acids, and salts of sulphated fatty alcohol glycol ethers, formaldehyde condensation products of sulphonated naphthalene and its derivatives, phenol and formaldehyde condensation of naphthalene and naphthalene sulphonic acids, polyoxyethylene octyl, octyl or nonyl phenol, alkyl phenyl and tributyl phenyl polyglycol ethers, alkyl aryl polyether alcohols, isotridecyl alcohol, ethylene oxide condensation of fatty alcohols, ethoxylated castor oil, polyoxy ethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol sterol, lignin sulphite waste liquors and methylcellulose.

Powders, spreads or dusts may be prepared by mixing or milling the active compounds with a solid carrier.

The active ingredient content of the formulations is generally from 0.01 to 95%, preferably from 0.1 to 90% by weight. The purity of the active compounds in the formulations is 90-100%, preferably 95-100%. (Based on their NMR spectrum)

Examples of compositions of the invention include:

Example 1

Thorough mixing of 135 parts by weight of active ingredient with 95 parts by weight of finely divided kaolin yields 5% by weight of a powder.

Example 2 Part by weight of the active ingredient is intimately mixed with a mixture consisting of 8 parts by weight of paraffin oil sprayed onto 92 parts by weight of powdered silica gel. Thus, a composition is obtained which provides good adhesion of the active ingredient. (Active ingredient content: 23% by weight).

EXAMPLE 3 Part by weight of the active ingredient is dissolved in 90 parts by weight of xylene

8-10 moles of ethylene oxide and 1 mole of oleic acid N-monoethanolamide in a reaction mixture of 6 parts by weight, 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 2 parts by weight of reaction product of 40 moles of ethylene oxide and 1 mole of castor oil. (Active ingredient content: 9% by weight).

EXAMPLE 4 Compounds of the active ingredient were dissolved in a mixture of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of a reaction product of 7 moles of ethylene oxide and 1 mole of isooctylphenol and 5 parts of a reaction product of 40 moles ethylene oxide. (Active ingredient content: 16% by weight).

EXAMPLE 5 3 parts by weight of the active ingredient are thoroughly mixed and ground in a hammer mill with 3 parts by weight of sodium salt of diisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of sodium salt of lignin sulphonic acid and 7 parts by weight of powder.

136 with silica gel. (Active ingredient content; 80% by weight).

EXAMPLE 6 Mixing 10 parts by weight of the active ingredient with 10 parts by weight of N-methyl-α-pyrrolidone gives a solution which can be applied to the finest droplets.- (Active ingredient content: 90% by weight).

Example 7 A portion of the active ingredient was dissolved in a mixture of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of a reaction product of 7 moles of ethylene oxide and 1 mole of isooctylphenol and 10 parts by weight of a reaction product of 40 moles ethylene oxide. The resulting solution is poured into 100,000 parts by weight of water and finely divided in water to give an aqueous dispersion containing 0.02% by weight of active ingredient.

EXAMPLE 8 3 parts by weight of the active ingredient are thoroughly mixed and ground in a hammer mill with 3 parts by weight of sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of sodium salt of lignin sulphonic acid and 60 parts by weight of silica gel powder. The resulting mixture was finely dispersed in 20,000 parts by weight of water to give a 0.1% by weight spray.

Granules such as coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers. Solid carriers include mineral products such as silica gel, silica, silica gel, silicates, talc, kaolin, attapulgite, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, core • · · • · · · ·

137 sodium oxide, ground plastics, fertilizers such as ammonium sulfate, phosphate and nitrate, urea and plant products such as cereal flour, cinnamon, wood and bone-shell meal, cellulose powder and other solid carriers.

The active compounds may be mixed with different types of oils, herbicides, fungicides, bactericides and other pesticides, optionally immediately before use (Tankmix).

These agents may be admixed with the compositions of the invention in a weight ratio of from 1: 10 to 10: 1.

Synthesis Example

The following synthesis examples were used to prepare additional compounds of formula (I) which were carried out by appropriate conversion of the starting compounds. The compounds thus obtained are listed in the table below together with their physical characteristics.

Example 9 (Ε, E) -2- (Methoxyimino) -2- [2- (1-acetyl-ethylimino-oxy-methyl) -phenyl] -acetic acid methyl ester

In 150 ml of anhydrous dimethylformamide, 21 g (0.21 mole) of 2- (hydroxyimino) was added under reduced pressure at room temperature with 6.4 g (0.21 mol) of sodium hydride (80%) under gentle cooling. 3-oxobutane and the reaction mixture was stirred at room temperature for half an hour. Finally, 60 g (0.21 mol) of methyl 2-methoxyimino-2- [2- (bromomethyl) phenyl] -acetic acid was added dropwise to the reaction mixture.

A solution of 360 ml of dimethylformamide was added and the reaction mixture was stirred at room temperature for a further 16 hours. Then 10% hydrochloric acid was added to the reaction mixture, followed by methyl

138

extraction with tert-butyl ether. The combined organic layers were washed with water, dried over sodium sulfate and evaporated. The residue was suspended in a little cold methanol. The filtrate was filtered off to give 38 g of the title compound as light brown crystals. (Yield: 59%)

Melting point: 69-71 ° C 'Ή-NMR (CDC1 _3): δ = l, 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 10 (Ε, Ε, E) -2- (Methoxyimino) -2- {2- [1-methyl-2- (ethoxyimino) -propylimino-oxymethyl] -phenyl} - acetic acid methyl ester

After cooling to room temperature from 2.5 g (8.2 mmol) of the title compound of Example 9 in 60 mL of hot methanol, 0.96 g (9.8 mmol) of ethoxyamine hydrochloride and 0.6 g of anhydrous molecular sieve granulate are added. (3 Å) and allowed to stand at room temperature for 5 days. After filtration of the molecular sieve, the filtrate is evaporated, the residue is taken up in a two-phase mixture of methyl tert-butyl ether and water, the organic phase is washed with water, dried over sodium sulfate and evaporated. The residue was triturated with hexane and filtered off to give 1.8 g of the title compound as pale yellow crystals. (Yield: 63%)

Melting point: 69-72 ° C ^X H-NMR (CDC1 _3): δ = l, 27 (t, 3H); l, 96 (s, 3H); l, 99 (s, 3H); 3.84 (s, 3H); 4.04 (s, 3H); 4.17 (q, 2H); 5.06 (s, 2H); 7.17-7.4 δ (m, 4H) ppm

Example 11 · • · · · · «· * * * *

139 (Ε, Ε, Ε) -2- (Methoxyimino) -2- {2- [1-methyl-2- (ethoxyimino) -propylimmonoxymethyl] -phenyl} -thioacetic acid S methyl ester

7.0 g (20 mmol) of the title compound of Example 10 are heated in 80 ml of 1M aqueous potassium hydroxide solution for 4 hours. After cooling, the reaction mixture is extracted with methyl tert-butyl ether, the aqueous phase is acidified with 1: 1 hydrochloric acid and extracted with methyl tert-butyl ether. The organic layer was washed with water, dried over sodium sulfate and evaporated to give 6.0 g of (Ε, Ε, E) -2- (methoxyimino) -2- {2- [1-methyl-2- ( ethoxyimino) -propylimino-oxymethyl] -phenyl} -acetic acid which is then dissolved in 100 ml of anhydrous dimethylformamide.

To the solution, 2.9 g (18 mmol) of carbonyldiimidazole was added and the reaction mixture was stirred for 1 hour and then added to the reaction mixture.

Sodium methane thiolate (2.5 g, 36 mmol) was added and the reaction stirred for an additional hour. The reaction mixture is evaporated, the residue is taken up in a biphasic mixture of methyl tert-butyl ether and water, the organic phase is extracted with 1M aqueous sodium hydroxide solution, washed with water, dried over sodium sulfate and evaporated. This gave 4.1 g of the title compound as a pale yellow oil. (Yield: 57%) ¹ H NMR (CDCl ₃ ): δ = 1.27 (t, 3H); l, 95 (s, 3H); l, 98 (s, 3H); 2.33 (s, 3H); 4.05 (s, 3H); 4.17 (q, 2H); 5.03 (s, 2H); 7.12-7.48 (m, 4H) ppm

Table 3

Compounds of formula (1.1) wherein

344 (R) _{m is} hydrogen, R and R are methyl.

• ·

140

Song R ⁵ Physical characteristics 1 methyl oil; IR (film): 2935, 1667, 1145, 1057, 1030, 1014, 988, 888, 881, 844, 773 ^cm-1 2 ethyl oil; IR (film): 2936, 1679, 1386, 1366, 1091, 1047, 1027, 982, 890, 847 cm ^-1

Examples of application against pest fungi:

The fungicidal activity of the compounds of the formula I is demonstrated by the following experiments:

® by weight of cyclohexanol, 20% by weight of Nekanyl

LN (Lutensol AP6, a wetting agent based on ethoxylated alkylphenol, emulsifying and dispersing) and 10% by weight ® ®

In a mixture of Emulphor EL (Emulan EL, an emulsifier based on ethoxylated fatty alcohols), a 20% emulsion of the active compounds was prepared and diluted with water to the desired concentration.

1. Erysiphe graminis var. tritici The leaves of Kanzler wheat germ plants were first treated with aqueous preparations containing 63 ppm of active ingredient and then treated with ca. After 24 hours, the experimental plants were pollinated with spores of wheat powdery mildew (Erysiphe graminis var. Tritici). Finally, the plants so treated were grown for another 7 days at 20-22 ° C and 75-80% RH. The degree of fungal infection was then evaluated.

This experiment showed that the plants treated with the compounds of the invention were not fungal infested, whereas the plants treated with one of the known active compounds (see compound 497 in Table 2 of EP-A 463 488) showed a untreated plants with 70% fungus • «· * ·

They showed 141 burns.

Examples of effects against animal pests.

The following experiments demonstrate the insecticidal activity of the compounds of formula (I):

From the active ingredients

the. ) in acetone 0.1% solution or ®

b. ) 70% by weight of cyclohexanol, 20% by weight of Necanyl

LN (Lutensol AP6, a wetting agent based on ethoxylated alkylphenol, emulsifying and dispersing) and 10% by weight ® ®

A mixture of Emulphor EL (Emulan EL, an emulsifier based on ethoxylated fatty alcohols) was formed into a 10% emulsion, which was worked up and diluted to the desired concentration in a) with acetone and b) with water.

At the end of the experiments, the lowest concentration at which the active compounds caused 80% to 100% inhibition or mortality compared to untreated controls was always determined. (Threshold or minimum concentration).

Claims (13)

Claims 1. Phenylthioacetic acid derivatives of the formula (I) and their salts, wherein the index value and the substituents have the following meanings: R ¹ is hydrogen, C 1-4 alkyl; R is halogen, cyano, nitro, trifluoromethyl, C 1-4 alkyl or C 1-4 alkoxy; m is 0, 1 or 2; and when m is 2, the two R ^{x 's} can be different from each other; R ³ is hydrogen, halogen, cyano, nitro, hydroxy, amino, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, C 1-4 haloalkoxy - C 1-4 alkylthio, C 1-4 alkylamino, or C 1-4 dialkylamino per alkyl moiety; R is hydrogen, halogen, cyano, nitro, hydroxy, amino, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylthio, C 1-6 alkylamino- , C1-C6 dialkylamino, C2-C6 alkenyl, C2-C6 alkenyloxy, C2-C6 alkenylthio, C2-C6 alkenylamino, in the alkenyl part 2-6 and in the alkyl moiety C 1 -C 6 N-alkenyl-N-alkylamino-C 2 -C 6 alkynyl, C 2 -C 6 alkynyloxy, C 2 -C 6 alkynylthio, C 2 -C 6 alkynyl amino - either an N-alkynyl-N-alkylamino group having 2 to 6 carbon atoms in the alkynyl moiety and 1 to 6 alkyl moieties in which the hydrocarbon group may be partially or completely halogenated, or the hydrocarbon group is as follows: One or three of the 143 groups may be substituted: halogen, cyano, nitro, hydroxy, mercapto, amino, carboxy, carbamoyl, thiocarbamoyl, C 1-6 alkylcarbamoyl in the alkyl moiety, C 1-6 alkyl in the alkyl moiety dialkylcarbamoyl, C 1-6 alkylthiocarbamoyl, C 1-6 dialkylthiocarbamoyl, C 1-6 alkylsulfonyl, C 1-6 alkylsulfinyl, C 1-6 alkoxy, alkyl; . C 1-6 haloalkoxy, C 1-6 alkoxycarbonyl, C 1-6 alkylthio, C 1-6 alkylamino, C 1-6 dialkylamino, alkyl in the alkoxy moiety, 2- C 6 -C 6 alkenyloxy, C 3 -C 6 cycloalkyl, C3-6cycloalkyloxy, heterocyclyl, heterocyclyl linked through an oxygen atom, aryl, aryloxy, C 1-4 arylalkoxy, arylthio, C 1-4 aryl in alkyl alkylthio, heteroaryl, heteroaryloxy, C 1 -C 4 heteroaryl-alkoxy, heteroarylthio, alkyl-C 1 -C 4 heteroaryl-alkylthio, wherein the ring moiety is partially or may be fully halogenated and / or the ring moiety may be substituted by one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxy, carbamoyl, thiocarbamoyl, C 1-6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylsulfinyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 halo- alkoxy, C 1-6 -alkoxycarbonyl, C 1-6 -alkylthio, C 1-6 -alkyl in the alkoxy moiety 1-6 carbon atoms per kilo amino moiety • · · 144 mos dialkylamino, C 1-6 alkylcarbamoyl in the alkyl moiety, C 1-6 dialkylcarbamoyl in the alkyl moiety, C 1-6 alkylthiocarbamoyl in the alkyl moiety C1-6 dialkylthiocarbamoyl, C2-6 alkenyl, C2-C6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy, heteroarylthio and -C (= NOR ⁶ ) -A _n -R ⁷ group; C3-6cycloalkyl, C3-6cycloalkyloxy, C3-6cycloalkylthio, C3-6cycloalkylamino, C3-6cycloalkyl and N-cycloalkyl1-6alkyl -N-alkylamino, C3-6cycloalkenyl, C3-6cycloalkenyloxy, C3-6cycloalkenylthio, C3-6cycloalkenylamino, 3-6 in the cycloalkenyl and alkyl C 1 -C 6 N-cycloalkenyl-N-alkylamino, heterocyclyl, heterocyclic group bonded via oxygen, sulfur or amino, substituted on the nitrogen by a heterocyclic group C 1-6 -alkylamino, aryl, aryloxy, arylthio, arylamino, C 1-6 -alkyl N-aryl-N-alkylamino, heteroaryl, heteroaryloxy- , heteroarylthio, heteroarylamino, C 1 -C 6 N-heteroaryl-N-alkylamino in the alkyl moiety, the ring moiety of which may be partially or fully halogenated, or the ring moiety of one to three of the following groups: may be substituted with: halogen, cyano, nitro, hydroxy, mercapto, amino, carboxy, carbamoyl, thiocarbamoyl, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkyl- sulfonyl C 1-6 alkyl145 sulfinyl, C3-6cycloalkyl, C1-6alkoxy, C 1-6 haloalkoxy, C 1-6 alkoxycarbonyl, C 1-6 alkylthio, C 1-6 alkylamino, C 1-6 dialkylamino per alkyl, in the alkyl moiety C 1-6 alkylcarbamoyl, per alkyl moiety C 1 -C 6 dialkylcarbamoyl, C 1 -C 6 alkylthiocarbamoyl, C 1 -C 6 dialkylthiocarbamoyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, benzyl, benzyl -oxy, aryl, aryloxy, heteroaryl and heteroaryloxy; 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 in the alkyl moiety, and 2 to 10 carbon atoms in the alkenyl moiety. C 3 -C 10 alkynylcarbonyl, C 3 -C 10 alkynylcarbonyl or C 1 -C 10 alkylsulfonyl group which may be partially or fully halogenated or which may be substituted by one to three of the following groups: halogen, cyano, nitro, , hydroxy, mercapto, amino, carboxy, carbamoyl, thiocarbamoyl, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkylsulfonyl, C 1-6 alkyl- sulfinyl, C 1-6 alkoxy, C 1-6 haloalkoxy, C 1-6 alkoxycarbonyl, C 1-6 alkylthio, C 1-6 alkylamino, alkyl in the alkyl moiety 1 C 6 -C 6 dialkylamino, C 1 -C 6 alkylcarbamoyl alkyl, C 1 -C 6 alkyl part alkyl kilcarbamoyl, with 1-6 carbon atoms per alkyl moiety of C 1-6 alkylthiocarbamoyl alkyl. C 146 dialkylthiocarbamoyl, C 2-6 alkenyl, C 2-6 alkenyloxy, C 3-6 cycloalkyl, C 3-6 cycloalkyloxy, heterocyclyl, heterocyclyl linked via oxygen, benzyl, benzyloxy, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy and heteroarylthio in which the cyclic moiety may be partially or fully halogenated or may be substituted by one to three of the moieties selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxy, carbamoyl, thiocarbamoyl, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkylsulfonyl, C 1-6 alkylsulfinyl, C 3-6 cycloalkyl, C 1-6 alkoxy, 1- C 6 -C 6 haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, C 1 -C 6 -alkylamino in alkyl, and alkyl in 1 -C 6 -alkyl; C 6 -alkylcarbamoyl, C 1-6 -alkylcarbamoyl per alkyl, in the alkyl C 1-6 alkylthiocarbamoyl, C 1-6 dialkylthiocarbamoyl, C 2-6 alkenyl, C 2-6 alkenyl, benzyl, benzyloxy, aryl, aryloxy , arylthio, heteroaryl, heteroaryloxy, heteroarylthio and -C (= NOR ⁶ ) -A _n -R ⁷ ; aryl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroarylcarbonyl or heteroarylsulfonyl groups which may be partially or fully halogenated or which may be substituted by one to three of the following groups: halogen, cyano, nitro -, hydroxy, mercapto, amino, carboxy, carbamoyl, thiocar. 147 bamoyl, (C 1 -C 6) alkyl, (C 1 -C 6) haloalkyl, (C 1 -C 6) alkylcarbonyl, (C 1 -C 6) alkylsulfonyl, (C 1 -C 6) alkylsulfinyl, -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- in the alkoxy moiety C 1-6 alkylalkylcarbamoyl, C 1-6 alkylcarbamoyl alkyl, C 1-6 dialkylcarbamoyl alkyl, C 1-6 alkylthiocarbamoyl alkyl, C 1-6 dialkylalkyl thiocarbamoyl, C2-C6 alkenyl, C2-C6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy and -C (= NOR ⁶ ) -A _n -R ⁷ group; in the formula A is oxygen, sulfur or nitrogen to which is attached a hydrogen atom or a C 1-6 alkyl group; n is 0 or 1; R ⁶ is hydrogen or C 1-6 alkyl; 7 _f R is hydrogen or C 1-6 alkyl. 2. (I) The compounds of formula I according to claim 1 and their salts, wherein R ^3, R ^{4 and} R j elentésűek the following: R is hydrogen, halogen, hydroxy, cyclopropyl, C 1-4 alkyl, C 1-4 alkoxy, or C 1-4 alkylthio; R ⁴ is hydrogen, halogen, hydroxy, cyclopropyl, cyclohexyl, C 1 -C 4 alkyl, C 1 -C 4 148 alkoxy, C 1-4 alkylthio, aryl or heteroaryl groups which may be partially or fully halogenated or substituted by one to three of the following groups: halogen, cyano, nitro, hydroxy, mercapto, amino, carboxy, carbamoyl, thiocarbamoyl, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkylsulfonyl, C 1-6 alkylsulfinyl, C 3-6 cycloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, C 1-6 alkoxycarbonyl, C 1-6 alkylthio, C 1-6 alkylamino, alkyl in the alkyl moiety C 6 -C 6 dialkylamino, C 1 -C 6 -alkylcarbamoyl in the alkyl moiety, C 1 -C 6 -alkylcarbamoyl in the alkyl moiety, in the alkyl moiety C 1 -C 6 alkylthiocarbamoyl, C 1 -C 6 dialkylthiocarbamoyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy , heteroaryl and heteroaryloxy; 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 in the alkyl moiety, and 2 to 10 carbon atoms in the alkenyl moiety. C 3 -C 10 alkynylcarbonyl, C 3 -C 10 alkynylcarbonyl or C 1 -C 10 alkylsulfonyl group which may be partially or fully halogenated or which may be substituted by one to three of the following groups: halogen, cyano, nitro, , hydroxy, mercapto, amino, carboxy, carbamoyl, thiocarbamoyl, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkylsulfonyl, C 1-6 alkyl- sulfinyl, C 3-6 149 cycloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, C 1-6 alkoxycarbonyl, C 1-6 alkylthio, C 1-6 alkylamino, alkyl in the alkoxy moiety C 1-6 dialkylamino, C 1-6 alkylcarbamoyl alkyl, C 1-6 dialkylcarbamoyl alkyl, C 1-6 alkylthiocarbamoyl alkyl, C 1-6 dialkylthiocarbamoyl alkyl; C2-C6 alkenyl, C2-C6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy and heteroarylthio, wherein the aromatic and heteroaromatic moieties may be partially or fully halogenated and / or wherein the aromatic and heteroaromatic moieties may be substituted by one to three of the following groups: halogen, cyano, nitro, hydroxy, mercapto, amino, carboxy; , carbamoyl, thiocarbamoyl, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 carbon C 1-6 alkylsulfonyl, C 1-6 alkylsulfinyl, C 3-6 cycloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, C 1-6 alkoxycarbonyl, C 1-6 alkylthio, C 1-6 alkylamino, C 1-6 dialkylamino per alkyl, in the alkyl moiety C 1-6 alkylcarbamoyl, per alkyl moiety C 1 -C 6 dialkylcarbamoyl, C 1 -C 6 alkylthiocarbamoyl, C 1 -C 6 dialkylthiocarbamoyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, benzyl, benzyl -oxy, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy, heteroarylthio and -C (= NOR) -A _n- R; 150 aryl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroarylcarbonyl or heteroarylsulfonyl groups which may be partially or fully halogenated or which may be substituted by one to three of the following groups: halogen, cyano, nitro, hydroxy, mercapto, amino, carboxy, carbamoyl, thiocarbamoyl, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkylcarbonyl, 1- C 6 -C 6 alkylsulfonyl, C 1 -C 6 alkylsulfinyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl in the alkoxy moiety C 1-6 alkylthio, C 1-6 alkylamino, C 1-6 dialkylamino per alkyl, C 1-6 alkylcarbamoyl alkyl, C 1-6 dialkylcarbamoyl alkyl, the alkyl moiety contains C 1-6 alkylthiocarbamoyl, the alkyl moiety C 1-6 dialkylthiocarbamoyl, C 2-6 alkenyl- , C2-6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, and -C (= NOR) -A _n -R; in the formula A is oxygen, sulfur or nitrogen to which is attached a hydrogen atom or a C 1-6 alkyl group; n is 0 or 1; R is hydrogen or C 1-6 alkyl; R is hydrogen or C 1-6 alkyl. Compounds of formula I according to claim 1, wherein m is 0. 4. Compounds of formula (I) according to claim 1, wherein R @ 3 is methyl, wherein R @ 1 is methyl. . 5. A process for the preparation of a compound of formula I according to claim 1, wherein R is other than a halogen atom, wherein a benzyl derivative of formula II, wherein L ^{1 is a} nucleophilically displaceable elimination group, is known per se. The reaction is carried out with an oxime of formula (III). A process for the preparation of a compound of formula (I) according to claim 1 wherein R and R are other than halogen, characterized in that a benzyl derivative of formula (II) according to claim 5 is known per se from (IV). Reaction with dioxime of formula (II) to form the corresponding benzyloxime of formula (V), which is then reacted with a compound of formula (VI), wherein L ^{2 is a} nucleophilically displaceable moiety, to a corresponding compound of formula (I). A process for the preparation of a compound of formula I according to claim 1, wherein R ³ is other than halogen, characterized in that a benzyl derivative of formula II according to claim 5 is known per se from a compound of formula (VIIa). by reaction with an oxooxime of formula VIII to form a corresponding benzyloxime of formula VIII, which is then either the. ) first with a hydroxylamine or a salt thereof and then with a compound of formula (VI) according to claim 6, or b. ) with a hydroxylamine derivative of formula IXa or a salt thereof of formula IXb wherein Q is an acid 152 anion is reacted to give the corresponding compound of formula (I). 8. An agent for controlling animal pests or pest fungi, which contain the usual additives and an active ingredient as defined in claim 1; An effective amount of a compound of formula (I) according to claim 1. 9. A method for controlling animal pests and pest fungi, comprising treating the animal pests or pest fungi, their habitat, or the plants, materials, surfaces or spaces to be rid of them, with an effective amount of a compound of formula I as claimed in claim 1. Use of compounds of formula (I) according to claim 1 for the preparation of compositions for controlling animal pests or fungi. Use of a compound of formula (I) according to claim 1 for controlling animal pests or pest fungi. 12. Compounds of formula VIII according to claim 7. 13. Use of compounds of formula VIII according to claim 7 as intermediates.