CA2231661A1 - Oxyaminooxime ethers, preparation thereof and intermediates therefor and compositions comprising them for controlling harmful fungi and animal pests - Google Patents

Oxyaminooxime ethers, preparation thereof and intermediates therefor and compositions comprising them for controlling harmful fungi and animal pests Download PDF

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CA2231661A1
CA2231661A1 CA002231661A CA2231661A CA2231661A1 CA 2231661 A1 CA2231661 A1 CA 2231661A1 CA 002231661 A CA002231661 A CA 002231661A CA 2231661 A CA2231661 A CA 2231661A CA 2231661 A1 CA2231661 A1 CA 2231661A1
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methyl
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Herbert Bayer
Hubert Sauter
Klaus Oberdorf
Wassilios Grammenos
Thomas Grote
Reinhard Kirstgen
Bernd Muller
Ruth Muller
Franz Rohl
Eberhard Ammermann
Volker Harries
Gisela Lorenz
Siegfried Strathmann
Norbert Gotz
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
    • C07C259/14—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/38—Amides of thiocarboxylic acids
    • C07C327/56—Amides of thiocarboxylic acids having nitrogen atoms of thiocarboxamide groups further bound to another hetero atom

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The disclosure concerns oxyamino oxime ethers of formula (I), wherein: X is NOCH3, CHOCH3, CHCH3; Y is O or NZ, Z being H or alkyl; R1 is H or alkyl; R2 is cyano, nitro, trifluoromethyl, halogen, alkyl or alkoxy, m = 0, 1 or 2 and the groups R2 can be different if m = 2; R3 is H, alkyl, alkyl halide or cycloalkyl; R4 is H or optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, heteroaryl; R5 is H or alkylsulphonyl, or optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl;
and their salts. Also disclosed are methods and intermediate products for use in producing them and their use for controlling harmful fungi and insect pests.

Description

CA 0223l66l l998-04-07 0050~46271 Oxyaminooxime ethers, preparation thereof and intermediates therefor and compositions comprising them for controlling harmful fungi and anima:L pests The present invention relates to oxyaminooxime ethers of the formula I

C = N----O--CH2 l ~ (R2~m (I) RsO - N / C=X

R4 C=O

Y-Rl where the variables have the following meanings:
X is NOCH3, CHOCH3 or CHCH3;
Y is O or NZ, Z being hydrogen or C1-C4-alkyl;
Rl is hydrogen or C1-C4-alkyl;
R2 is cyano, nitro, ha:Logen, Cl-C4-alkyl, trifluoromethyl or C1-C4-alkoxy;
m is 0, 1 or 2, it be:ing possible for the radicals R2 to be different if m is 2;
R3 is hydrogen, alkyl, haloalkyl or cycloalkyl;
R4 is hydrogen or unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl,. cycloalkenyl, heterocyclyl, aryl or heteroaryl;
R5 is hydrogen, alkylsulfonyl or unsubstituted or substituted alkyl, alkenyl, alkynyl or cycloalkyl, 35 and their salts.

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

Pheny]Lacetic acid derivatives having fungicidal and insecticidal action are disclosed in the following publications:
WO-A 93/16986, WO-A 94/14761 and WO-A 94/14322. With respect to their action, however, the active compounds disclosed therein are 45 not a]ways satisfactory.

0050./4627 1 It is an object of the present invention to provide novel compounds of this type having improved action against harmful fungi and pests.

5 We have found that this object is achieved by the oxyaminooxime ethers I defined at the outset. We have also found processes and intermediates for their preparation, as well as compositions compr-ising them for controlling animal pests and harmful fungi and t:heir use for this purpose.
The compounds I are obtainable in various ways by processes known per se from the literature.

In principle, it is insignificant in the synthesis of the 15 compounds I whether the group -C(X)-CO-YRl or the group -CH2oN=C(R3)-N(R4)-oR5 is synthesized first.

The synthesis of the group -C(X)-CO-YRl is disclosed, for example, in the following publications: EP-A 422 597, EP-A 463 488, 20 EP-A 370 629, EP-A 460 575, EP-A 472 300, W0-A 90/07493, W0-A 92/13830, W0-A 92/18487, DE-A 44 20 416.

l.l [n the synthesis of the group -CH2oN=C(R3)-N(R4)-oR5, a procedure is in general used in which a benzyl derivative of the formula II is reacted with a hydroxyimine of the :Eormula III.

~ ~(R2)m C = NOH + Ll _ CH2 R50 - N C=X

R4 C=O

III Y-R

~ ,~(R2)m C = ~ O--CH2 T
R50 --N ~ C=X

R4 C=O

Y-R

L1 in the formula II is a nucleophilically replaceable leaving group, eg. halogen or sulfonate groups [sic], preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.

The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, eg. sodium hydride, potassium hydroxide, potassium carbonate or triethylamine according to the methods described in Houben-Weyl, 4th Edition, Vol. E 14b, p. 370 et seq. and Vol. 10/1, p. 1189 et seq.

1.2 The hydroxyimine III needed is obtained, for example, by reaction of a thioamide VII with hydroxylamine or its salt (preferably: hydroxylammonium halide).

C = S H2NOH C = NOH

The reaction is carried out in a -nner known per se (cf. J.
Heterocycl. Chem. 17, 819 (1980); Houben-Weyl, 4th Edition, Volume VIII, page 694 et seq.) in an inert organic solvent.

A few thioamides VII are known (cf. Acta Cienc. Indica, Chem.
11, 124 (1985); J. Org. Chem. 51, 5198 (1986); J. Org. Chem.
52, 2927 (1987); Tetrahedron Lett. 24, 1851 (1983)), The thioamides VIIa are novel. They can be prepared in analoqy to the known methods.
R3~
C = S
R5~o - N / VIIa I

1.3 A further possibility for preparing the hydroxyimines III
consists in reacting a hydroxylamine derivative of the formula VIII with a hydroximic acid derivative of the formula IX in a manner known per se in an inert organic solvent, if appropriate using a base (see Chem.-Ztg. 100, 236 (1976);
Chem. Ber. 108, 2764 (1975); J. Org. Chem. 41, 2985 (1976)).

$1.50-- N --H
+ L2--C= NOH

R
C = NOH

I

III
L2 is a displaceable group such as amino, halogen, alkylsulfonyl or Cl C4-alkoxy, preferably amino, chlorine, bromine, methylsulfonyl, methoxy or ethoxy.

The compounds VIII and IX are known or can be prepared by miethods known per se (cf. J. Org. Chem. 47, 1171 (1982);
Tetrahedron 48, 6335 (1992); J. Heterocycl. Chem. 12, 1063 ( 1975); Am. Chem. J. 38, 257 ~1907); Tetrahedron 40, 2985 (1984); Helv. Chim. Acta 69, 1137 (1986)).
2. Alternatively, the compounds I can also be obtained by reacting the benzyl derivative II first with the hydroxyaminohydroxyimino derivative IV to give a corresponding benzyloxime of the formula V, V then being reacted with a compound VI to give I.

OO50~' 4627 R3 ~
C= NOH Ll--CH ~ ~(R2)m HO--N
I C=X

R4 C =O
IV ¦ II
Y-R

~¢~ ( R2 ) m C= N--O--CH2 HO - N C=X

R4 C=O V

Y-R

,, ~ ( R2 )m C = N- O - CH2 r R5-L3 R50 - N ~ C=X
VI l l R4 C=O
I

Y-R

IL3 = nucleophilically replaceable leaving group such as halogen, eg. chlorine, bromine, sulfonate eg. mesylate, t:rifate [sic], tesylate [sic]) l'he reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, eg.
potassium carbonate, potassium hydroxide, sodium hydride, pyridine or triethylamine according to the methods described in Houben-Weyl, 4th Edition, Vol. 10/1, p. 1189 et seq.;
ibid., Vol. E 14b, p. 307 et seq., p. 370 et seq. and p. 385 et seq.; ibid., Vol. 10/4, p. 55 et seq., p. 180 et seq. and E). 217 et seq.; ibid., Vol. E 5, p. 780 et seq. and Farmaco.
E~d. Sci. 39, 1060 (1984). The synthesis of the compounds IV
has already been described above.
3. A further possibili1y for preparing the compounds I is the reaction of the ben~yl derivative II with N-hydroxyphthal-imide, subsequent hydrazinolysis to the benzylhydroxylamine IIa and further reaction of IIa with a thioamide VII.

[ ~ ~ N-OH + Ll - CH

C=O II
I

Y-R

~ N - o - CH2 ~ (R2)m ll C=X
O ¦ H2NNH2 C=O
I

y=

~ ~ (R2)m R3 H2N--O--CH2 -f c= s C=X +R50 - N
C=O IIa Y-Rl VII

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 or DE-~ 42 28 867 or according to the conversion VII III (see above).
4. Correspondingly, the compounds I can also be obtained by reacting the benzylhydroxylamine IIa first with the hydroxy-thioamide VIIa to give the corresponding benzyloxyimino derivative of the formula V, V then being reacted with the compound VI as described above to give I.

~ ( R2 ) m C= S + H2N--O--CH2 HO - N C=X
C=0 IIa VIIa Y-Rl ~R3 ~ (R2)m C = N- 0 - CH2 HO - N C=X
l l R4 C=0 V
I

Y-R

VI ~ ~ (R2)m C = N ~ 0 - CH2 r RsO - N C=X

R4 C=0 Y-Rl 5. Alternatively, the compounds I can also be prepared by reacting a hydroxylamine derivative of the formula VIII with a hydroximic acid derivative of the formula X in a manner known per se in an inert organic solvent (cf. Collect. Czech.
Chem. Commun. 48, 596 (1983)).

R3 ~(R2 )m R50 - N - H + C = N- O - CH2 L4 C=X

C=O X
VIII
Y-R

J~(R2)m C= ~ O--CH2 '~
RsO - N / C=X
R4 C=0 I

Y-R

L4 iS a displaceable group such as amino, halogen, sulfonyl or C1-C4-alkoxy, preferably amino, chlorine, bromine, methylsulfonyl, methoxy or ethoxy.

The compounds X are known (cf. WO-A 94/14761, EP-A 463 488, WO-A 92/18487) or can be prepared by methods known per se.
6. In addition, the compounds I are obtained by converting a compound III according to the methods described in EP-A 493 711 with a lactone XI first into the corresponding benzoic acid XII and converting XII via the corresponding halides XIII into the cyanocarboxylic acids XIV, which are converted by way of the Pinner reaction (Angew. Chem. 94, 1 (1982)) into the a-ketoesters XV and, if appropriate, reacted further to give the a-ketoamides XVI (cf. EP-A 348 766, DE-A 37 05 389, EP-A 178 826, DE-A 36 23 921, Houben-Weyl, 4th Edition, Vol. E5, p. 941 et seq.).

0050~46271 C = NOH o ~ (R2)m R50--N ll S l O

III
~ J~--(R2)m C = N - O - CH2 ~
R50 - N ~ C=O XII

lSR4 OH

C== N--O--CH2/~
20R50 - N ~ C=O XIII

R4 Hal R3 ~ (R2)m C=~O--CH2 ~r 30R50 - N ~ C=O XIV

C = N - O - CH2 ~ (R2)m Rl~H
R50 - N C=O XV

~ f~(R2)m C = N--O--CH2~' ~
R50 - N ~ C=O XVI
R4 CON(Z)R

(Z = hydrogen or C1-C4-alkyl) 10 The a-ketoesters XV and the a-ketoamides XIV can be converted into the compounds I according to customary processes (cf.
EP-A 178 826, EP-A 348 766, DE-A 36 23 921, DE-A 37 05 389 and the literature cited at the outset).

15 Compounds I in which Rl is hydrogen are obtained according to this process by hydrolysis of the esters XV and subsequent reaction to give I.

The compounds I in which Y is NZ can also be obtained from the 20 esters (Y=O) by reaction with the appropriate amines HN(Z)Rl.

The compounds II are disclosed in EP-A 513 580, EP-A 477 631, EP-A 463 488, EP-A 251 082, EP-A 400 417 and/or EP-A 585 751 or can be prepared by the methods described there.
The compounds I can be present in the form of their salts, the nature of the salt generally not mattering. The preparation of the salts of compounds of the formula I is carried out in a manner known per se.
The compounds I can be obtAine~ during preparation, on account of their C=C and C=N double bonds, as E/Z isomer mixtures, which can be Reparated, for example, into the individual compounds in a customary manner by crystallization or chromatography.
If isomer mixtures are formed during synthesis, in general, however, a separation of the isomers is not absolutely necessary, as the individual isomers can be partially converted into one another during preparation for application or during application 40 (eg. under the action of light, acid or base). Corresponding conversions can also take place after application, for example during the treatment of plants, in the treated plant or in the harmful fungus or animal pest to be controlled.

0050~4627 1 With regard to the C=X double bond, with respect to their activity, the E isomers of the compounds I are preferred (configuration based on the -OCH3 or the -CH3 group in relation to the -COYRl group).

With regard to the -C(R3)=NoCH2- double bond, with respect to their activity, the cis-isomers of the compounds I are preferred (configuration based on the radical R3 in relation to the -OCH2-group).
In the definitions of the compounds I given at the outset, collective terms were used which are generally representative of the following groups:
15 halogen: fluorine, chlorine, bromine and iodine;

alkyl: straight-chain or branched alkyl groups having 1 to 4, 1 to 6 or 1 to 10 carbon atoms, eg. Cl-C6-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 20 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 25 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

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

dialkylamino: an amino group which carries two straight-chain or 35 branched alkyl groups which are independent of one another, each having 1 to 6 carbon atoms as mentioned above;

alkylcarbonyl: straight-chain or branched alkyl groups having 1 to 10 carbon atoms, which are bonded to the structure via a 40 carbonyl group (-C0-);

alkylsulfonyl: straight-chain or branched alkyl groups having 1 to 6 or 1 to 10 carbon atoms, which are bonded to the structure via a sulfonyl group (-S02- );

alkylsulfoxyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, which are bonded to the structure via a sulfoxyl group (-S(=0)-);

5 alkylaminoc~rbonyl: alkylamino groups having 1 to 6 carbon atoms as mentioned above, which are bonded to the structure via a carbonyl group (-C0-);

dialkylaminoc~rbonyl: dialkylamino groups each having 1 to 6 10 carbon atoms per alkyl radical as mentioned above, which are bonded to the structure via a carbonyl group (-C0-);

alkylaminothio~rbonyl: alkylamino groups having 1 to 6 carbon atoms as mentioned above, which are bonded to the structure via a 15 thiocarbonyl group (-CS-);

dialkylaminothior~rbonyl: dialkylamino groups each having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the structure via a thiocarbonyl group (-CS-);
haloalkyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, it being possible in these groups for the hydrogen atoms to be partially or completely replaced by halogen atoms as mentioned above, eg. Cl-C2-haloalkyl such as chloromethyl, 25 dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 30 2,2,2-trichloroethyl and pentafluoroethyl;

alkoxy: straight-chain or branched alkyl groups having 1 to 4 or 1 to 6 carbon atoms as mentioned above, which are bonded to the structure via an oxygen atom (-0-), eg. Cl-C6-alkoxy such as 35 methoxy, ethoxy, propoxy, l-methylethoxy, butoxy, l-methyl-propoxy, 2-methylpropoxy, l,l-dimethylethoxy, pentoxy, l-methyl-butoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methyl-40 pentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethyl-butoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethyl-butoxy, l-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy;

alkoxycarbonyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, which are bonded to the structure via an oxycarbonyl group (-OC(=0)-);

5 haloalkoxy: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, it being possible for the hydrogen atoms in these groups to be partially or completely replaced by halogen atoms such as mentioned above, and these groups being bonded to the structure via an oxygen atom;
alkylthio: straight-chain or branched alkyl groups having 1 to 4 or 1 to 6 carbon atoms as mentioned above, which are bonded to the structure via a sulfur atom (-S-), eg. C1-C6-alkylthio such as methy.lthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 15 l-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutyl-thio, 2,2-dimethylpropylthio, l-ethylpropylthio, hexylthio, l,l-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentyl-thio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio~
20 l,1-d.imethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutyl-thio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethyl-butylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethyl-propylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio;
cycloAl~yl: monocyclic alkyl groups having 3 to 6 carbon ring members, eg. cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

alkenyl: straight-chain or branched alkenyl groups having 2 to 6 30 or 2 to 10 carbon atoms and a double bond in any desired position, eg. C2-C6-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 35 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 40 l-ethyl-l-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, l-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, l-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 45 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 5 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, l-ethyl-l-butenyl, l-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 10 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

alkenyloxy: straight-chain or branched alkenyl groups having 2 to 6 carbon atoms and a double bond in any desired position, which are bonded to the structure via an oxygen atom (-0-);
alkenylthio or alkenylamino: straight-chain or branched alkenyl groups having 2 to 6 carbon atoms and a double bond in any desired position, which (alkenylthio) are bonded to the structure via a sulfur atom or (alkenylamino) a nitrogen atom.
alkenylcarbonyl: straight-chain or branched alkenyl groups having 2 to 10 carbon atoms and a double bond in any desired position, which are bonded to the structure via a carbonyl group (-C0-);

25 alkynyl: straight-chain or branched alkynyl groups having 2 to 10 carbon atoms and a triple bond in any desired position, eg.
C2-C6-alkynyl such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, l-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 30 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, l-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-35 3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

alkynyloxy or alkynylthio and alkynylamino: straight-chain or branched alkynyl groups having 2 to 6 carbon atoms and a triple 40 bond in any desired position, which (alkynyloxy) are bonded to the structure via an oxygen atom or (alkynylthio) via a sulfur atom or (alkynylamino) via a nitrogen atom;

alkynylcarbonyl: straight-chain or branched alkynyl groups having 45 3 to 10 carbon atoms and a triple bond in any desired position, which are bonded to the structure via a carbonyl group (-C0-);

cyclo~l~enyl or cyclo~ nyloxy cyclo~lkenylthio and cyclo-alkenylr ino: monocyclic alkenyl groups having 4 to 6 carbon ring '~rs, which are bonded to the structure directly or (cyclo-alkenyloxy) via an oxygen atom or (cycloalkenylthio~ a sulfur 5 atom or cycloalkenylamino) via a nitrogen atom, eg. cyclobutenyl, cyclopentenyl and cyclohexenyl.

cyclo~l~o~yl ~sicl or cycloalkylthio and cycloalkylr ino:
monocyclic alkyl groups having 3 to 6 carbon ring members, which 10 are bonded to the structure (cycloalkoxy) via an oxygen atom or (cycloalkylthio) a sulfur atom or (cycloalkylamino) via a nitrogen atom, eg. cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

15 heterocyclyl or heterocyclyloxy. heterocyclylthio and hetero-cyclylamino: three- to six-membered, saturated or partially unsaturated mono- or polycyclic heterocycles which contain one to three heteroatoms selected from a group consisting of oxygen, nitrogen and sulfur, and which are bonded to the structure 20 directly or (heterocyclyloxy) via an oxygen atom or (hetero-cyclylthio) via a sulfur atom or (heterocyclylamino) via a nitrogen atom, such as 2-tetrahydrofuranyl, oxiranyl, 3-tetra-hydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 2s 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thia-zolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxa-30 diazolidin-3-yl, 1,2,4-oYA~i~7olidin-5-yl, 1,2,4-thia-diazolidin-3-yl, 1,2,4-th;~ zolidin-5-yl, 1,2,4-tria-zolidin-3-yl, 1,3,4-oYA~i~zolidin-2-yl, 1,3,4-thia-diazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,3-dihydrofur-4-yl, 2,3-dihydrofur-5-yl, 35 2,5-dihydrofur-2-yl, 2,5-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,3-dihydrothien-4-yl, 2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl, 2,5-dihydro-thien-3-yl, 2,3-dihydl G~L1 ol-2-yl, 2,3-dihydropyrrol-3-yl, 2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl, 2,5-dihydro-40 pyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydro-isoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydro-isoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2,5-dihydro-isoxazol-4-yl, 2,5-dihydrooxazol-5-yl, 45 2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl, 4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl, (~050/ 4627 1 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydro-pyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,5-dihydro-5 pyrazol-3-yl, 2,5-dihydropyrazol-4-yl, 2,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydro-oxazol-5-yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl, 2,5-dihydro-oxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrothiazol-2-yl, 10 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 4,5-dihydro-thiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydro-thiazol-5-yl, 2,3-dihydroimidazol-2-yl, 2~3-dihydroimidazol-4 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydro-15 imidazol-4-yl, 4,5-dihydroimidazol-5-yl, 2,5-dihydroimida_ zol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5_yl, 2-morpholinyl, 3-morpholinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydro-20 pyrimidinyl, 2-tetrahydropyrazinyl, 1,3,5-tetrahydrotriazin-2-yl, 1,2,4-tetrahydrotriazin-3-yl, 1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl, 2-tetrahydropyranyl, 1,3-dioxolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl, 4H-3,1-benzothiazin-2-yl, 1,1-dioxo-2,3,4,5-tetrahydrothien-2-yl, 25 2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl and 1,3-dihydrooxazin-2-yl;

aryl or aryloxy, arylthio arylcarbonyl and arylsulfonyl:
aromatic mono- or polycyclic hydrocarbon radicals which are 30 bonded to the structure directly or (aryloxy) via an oxygen atom ~-O-) or (arylthio) a sulfur atom (-S-), (arylcarbonyl) via a carbonyl group (-C0-) or (arylsulfonyl) via a sulfonyl group (-SO2-), eg. phenyl, naphthyl and phenanthrenyl or phenoxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl 35 and sulfonyl radicals;

aryl: ino: aromatic mono- or polycyclic hydrocarbon radicals, as mentioned above, which are bonded to the structure via a nitrogen atom.
heteroaryl or heteroaryloxy, heteroarylthio, heteroarylcarbonyl and hetarylsulfonyl: aromatic mono- or polycyclic radicals which, beside carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and an oxygen or a 45 sulfur atom or an oxygen or a sulfur atom and which are bonded to the structure directly or (heteroaryloxy) via an oxygen atom (-o-) or (heteroarylthio) a sulfur atom (-s-)~ (heteroaryl-0050/46~71 carbonyl) via a carbonyl group (-CO-) or (heteroarylsulfonyl) via a sulfonyl group (-S02-), eg.

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

- benzo-fused 5-membered heteroaryl, cont~ining one to three nitrogen atoms or a nitrogen atom and/or an oxygen or sulfur atom: 5-membered ring heteroaryl groups which, beside carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom or an oxygen or a sulfur atom as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group;
- 5-membered heteroaryl bonded via nitrogen, cont~ining one to four nitrogen atoms, or benzo-fused 5-membered heteroaryl bonded via nitrogen, containing one to three nitrogen atoms:
5-membered ring heteroaryl groups which, beside carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group, these rings being bonded to the structure via one of the 45 nitrogen ring ~ ers;

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

lO - benzo-fused 6 ~ered heteroaryl containing one to four nitrogen atoms: 6-membered ring heteroaryl groups in which two adjacent carbon ring members can be bridged by a buta-1,3-diene-1,4-diyl group, eg. quinoline, isoquinoline, quinazoline and quinoxaline, - pyrido[3,2-dlthiazol-2-yl;
or the corresponding oxy, thio, carbonyl or sulfonyl groups;

20 hetary~ Q: aromatic mono- or polycyclic radicals which, beside carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and an oxygen or a sulfur atom and which are bonded to the structure via a nitrogen atom.
The statement Npartially or completely halogenated" is inten~A
to express that in the groups characterized in this way the hydrogen atoms can be partially or completely replaced by identical or different halogen atoms, as mentioned above.
The statement "unsubstituted or substitutedn is inten~eA to express that in the groups characterized in this way the hydrogen atoms can be partially or completely replaced by identical or different groups of, for example, the type which are mentioned 35 under the collective terms set out above.

With respect to their biological action, compounds of the formula I are preferred in which the variables have the following meanings:

X iS NOCH3, CHOCH3 or CHCH3;

Y is 0 or NZ, Z being hydrogen or C1-C4-alkyl;
45 R1 is hydrogen or Cl-C4-alkyl;

R2 is cyano, nitro, halogen, Cl-C4-alkyl, trifluoromethyl or C1-C4-alkoxy;

m is 0, 1 or 2, it being possible for the radicals R2 to be different if m is 2;

R3 is hydrogen, C1-C4-alkyl, Cl-C4-haloalkyl or cyclopropyl;

R4 is hydrogen;
C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, it being possible for the three last-mentioned radicals to be partially or completely halogenated and/or to carry one to three substituents, in each case selected from the group: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, Cl-C6-alkylaminocarbonyl, di-C1-C6-alkyl-aminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkyl-aminothiocarbonyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, Cl-C6-alkoxy, Cl-C6-haloalkoxy, Cl-C6-alkoxycarbonyl, Cl-C6-alkylthio, Cl-C6-alkylamino, di-Cl-C6-alkylamino, C2-C6-alkenyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C1-C4-alkoxy, arylthio, aryl-Cl-C4-alkylthio, heteroaryl, hetero-aryloxy, heteroaryl-C1-C4-alkoxy, heteroarylthio or hetero-aryl-Cl-C4-alkylthio, it being possible for the cyclic groups of the fourteen last-mentioned radicals for their part to be partially or completely halogenated and/or to carry one to three substituents, in each case selected from the group:
cyano, nitro, hydroxyl, mercapto, amino, carboxyl, amino-carbonyl, aminothiocarbonyl, Cl-C6-alkyl, Cl-C6-haloalkyl, Cl-C6-alkylcarbonyl, Cl-C6-alkylsulfonyl, Cl-C6-alkylsulfoxyl, C3-C6-cycloalkyl, Cl-C6-alkoxy, Cl-C6-haloalkoxy, Cl-C6-alkoxy-carbonyl, Cl-C6-alkylthio, Cl-C6-alkylamino, di-Cl-C6-alkyl-amino, Cl-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, Cl-C6-alkylaminothiocarbonyl, di-Cl-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy, heteroarylthio, C3-C6-alkynyloxy, Cl-C4-alkylenedioxy, which can be halogenated, or C(=NoR6)-An-R7, A being oxygen, sulfur or nitrogen and the nitrogen carrying hydrogen or Cl-C6-alkyl, n being equal to 0 or 1, R6 being hydrogen or C1-C6-alkyl and R7 being hydrogen or Cl-C6-alkyl;

C3-C6-cycloalkyl, C4-C6-cycloalkenyl, heterocyclyl, it being possible for the three last-mentioned radicals to be partially or completely halogenated and/or to carry one to three substituents, in each case selected from the group:

cyano, Cl-C6-alkyl, Cl-C6-haloalkyl, C2-C6-alkenyl, Cl-C6-alkoxy and C1-C6-alkylthio;

aryl or heteroaryl, it being possible for these two radicals to be partially or completely halogenated and/or to carry one to three substituents, in each case selected from the group:
cyano, nitro, hydroxyl, mercapto, amino, carboxyl, amino-carbonyl, aminothiocarbonyl, Cl-C6-alkyl, Cl-C6-haloalkyl, Cl-C6-alkylcarbonyl, Cl-C6-alkylsulfonyl, Cl-C6-alkylsulfoxyl, C3-C6-cycloalkyl, Cl-C6-alkoxy, Cl-C6-haloalkoxy, Cl-C6-alkoxy-carbonyl, Cl-C6-alkylthio, Cl-C6-alkylamino, di-Cl-C6-alkyl-amino, C1-C6-alkylaminocarbonyl, di-Cl-C6-alkylaminocarbonyl, Cl-C6-alkylaminothiocarbonyl, di-Cl-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C3-C6-alkynyloxy, C1-C4-alkylenedioxy, which can be halogenated, benzyl, benzyl-oxy, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy, heteroarylthio, it being possible for the cyclic groups of the eight last-mentioned radicals for their part to be partially or completely halogenated and/or to carry one to three substituents, in each case selected from the group:
cyano, nitro, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, Cl-C6-alkylcarbonyl, C3-C6-cycloalkyl, Cl-C6-alkoxy, Cl-C6-haloalkoxy, Cl-C6-alkoxycarbonyl, Cl-C6-alkylthio, Cl-C6-alkylamino, di-Cl-C6-alkylamino, C2-C6-alkenyl, C2-C6-alkenyloxy, C3-C6-alkynyloxy and C1-C4-alkylenedioxy, which can be halogenated; and C(=NOR6 ) -An-R7, A being oxygen, sulfur or nitrogen and the nitrogen carrying hydrogen or C1-C6-alkyl, n being equal to 0 or 1, R6 being hydrogen or C1-C6-alkyl and R7 being hydrogen or C1-C6-alkyl;
R5 is hydrogen, C1-C6-alkylsulfonyl, Cl-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, it being possible for these radicals to be partially or completely halogenated and/or to carry one to three substituents, in each case selected from the group: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, Cl-C6-alkylaminocarbonyl, di-Cl-C6-alkylaminocarbonyl, Cl-C6-alkylaminothiocarbonyl, di-Cl-C6-alkylaminothiocarbonyl, Cl-C6-alkylsulfonyl, Cl-C6-alkylsulfoxyl, Cl-C6-alkoxy, Cl-C6-haloalkoxy, Cl-C6-alkoxycarbonyl, Cl-C6-alkylthio, Cl-C6-alkylamino, di-Cl-C6-alkylamino, C2-C6-alkenyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, heterocyclyl, hetero-cyclyloxy, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy and heteroarylthio, it being possible for the cyclic groups of the 10 last-mentioned radicals for their part to be partially or completely halogenated and/or to carry one to three of the following substituents, in each case selected 0050/46;!7 1 from the group: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, Cl-C6-alkyl, Cl-C6-haloalkyl, Cl-C6-alkylcarbonyl, Cl-C6-alkylsulfonyl, Cl-C6-alkylsulfoxyl, C3-C6-cycloalkyl, Cl-C6-alkoxy, Cl-C6-haloalkoxy, Cl-C6-alkoxycarbonyl, C1-C6-alkylthio, Cl-C6-alkylamino, di-Cl-C6-alkylamino, Cl-C6-alkylamino-carbonyl, di-C1-C6-alkylaminocarbonyl, Cl-C6-alkylaminothio-carbonyl, di-Cl-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy, heteroarylthio and C3-C6-alkynyloxy, C3-C6-cycloalkyl, which can be partially or completely halogenated and/or can carry one to three substituents, in each case selected from the group: cyano, Cl-C6-alkyl, Cl-C6-haloalkyl, C2-C6-alkenyl, Cl-C6-alkoxy and Cl-C6-alkylthio;

and their salts.
Furthermore, compounds of the formula I are preferred in which m is 0.

Equally preferred compounds of the formula I are those in which Rl 25 is methyl.

In addition, compounds I are preferred in which R3 is hydrogen, cyclopropyl, methyl, ethyl, 1-methylethyl or trifluoromethyl.

30 Particularly preferred compounds I are those in which R3 is methyl.

In addition, compounds I are preferred in which R3 is trifluoromethyl.
In addition, compounds I are preferred in which R4 is unsubstituted or substituted C1-C6-alkyl, C2-C6-alkenyl or C2 -C6-alkynyl .

40 Additionally, compounds I are preferred in which R4 is unsubstituted or substituted heterocyclyl or unsubstituted or substituted C4-C6-cycloalkenyl.

Additionally, compounds I are preferred in which R4 is 45 unsubstituted or substituted C3-C6-cycloalkyl.

UU3U~ StO~ I 1 In addition, compounds I are preferred in which R4 is unsubstituted or substituted aryl or hetaryl.

In addition, compounds I are preferred in which R4 is unsubst. or 5 subst. pyridyl, pyrimidyl, pyrazinyl, pyridazinyl or triazinyl.

In addition, compounds I are preferred in which R4 is unsubst. or subst. furyl, thienyl or pyrrolyl.

10 In addition, compounds I are preferred in which R4 is unsubst. or subst. oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazolyl.

In addition, c~ _unds I are preferred in which R4 is unsubst. or 15 subst. oxdiazolyl [sic], thiadiazolyl or triazolyl.

Additionally, compounds I are preferred in which R4 is phenyl which is unsubstituted or carries one or two of the following groups: nitro, cyano, hydroxyl, amino, aminocarbonyl, amino-20 thiocarbonyl, halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, C3-C6-cyclo-alkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy, Cl-C4-alkylamino, Cl-C4-alkylcarbonyl, di-Cl-C4-alkylamino, Cl-C4-alkylsulfonyl, Cl-C4-alkoxycarbOnyl, Cl-C4-alkylaminocarbonyl, di-Cl-C4-alkyl-aminocarbonyl, C1-C4-alkylthio, C2-C6-alkenyl, C2-C6-alkenyloxy, 25 C3-C6-alkynyloxy and Cl-C4-alkylenedioxy, which can be halogenated.

In addition, compounds I are preferred in which R5 is Cl-C6-alkyl.

30 Additionally, compounds I are preferred in which Rs is methyl or ethyl.

In addition, compounds I are preferred in which R5 is hydrogen.

35 Additionally, compounds I are preferred in which R5 is C3-C6-alkenyl.

Additionally, compounds I are preferred in which Rs is C3-C6-alkynyl .
In addition, compounds of the formula I are preferred in which X
is NOCH3.

In addition, compounds of the formula I are preferred in which X
45 is CHOCH3.

.)050/ 4627 1 In addition, compounds of the formula I are preferred in which X
is CHCH3.

In addition, compounds of the formula I are preferred in which Y
5 is 0.

Additionally, compounds of the formula I are preferred in which Y
is NH.

10 In particular, with respect to their use, the compounds I
compiled in the following tables are preferred.

The following tables (1 to 596) are based on the formulae I.l, I.2, I.3 and I.4, the double bonds marked by "E having the E
15 configuration:

R3 ~
C=~O--CH2~ (I.l) R50--N~ E E C=CH-OCH3 R4 C=O

C= N--O--CH2$1 ( I . 2 ) R50--N~ E E 7=CH-CH3 R4 C=O

C = N--O - CH2 ~ (I.3) R50--N ~ E E C=N-OCH3 R4 C=O

C = N- O - CH2 ~ (I.4) R50 - N ~ - E C=N-OCH3 R4 C=O

Table 1 Compounds of the formula I.l., where R3 = hydrogen;
15 RS = hydrogen;
R4 = in each case one line of Table A.

Table 2 Compounds of the formula I.2, where 20 R3 = hydrogen;
R5 = hydrogen;
R4 = in each case one line of Table A.

Table 3 25 Compounds of the formula I.3, where R3 = hydrogen;
R5 = hydrogen;
R4 = in each case one line of Table A.

30 Table 4 Compounds of the formula I.4, where R3 = hydrogen;
R5 = hydrogen;
R4 = in each case one line of Table A.
Table 5 C~ unds of the formula I.1., where R3 = hydrogen;
R5 = methyl;
40 R4 = in each case one line of Table A.

Table 6 Compounds of the formula I.2, where R3 = hydrogen;
45 R5 = methyl;
R4 = in each case one line of Table A.

Table 7 Compounds of the formula I.3, where R3 = hydrogen;
R5 = methyl;
5 R4 = in each case one line of Table A.

Table 8 Compounds of the formula I.4, where R3 = hydrogen;
10 R5 = methyl;
R4 = in each case one line of Table A.

Table 9 Compounds of the formula I.l, where 15 R3 = hydrogen;
R5 = ethyl;
R4 = in each case one line of Table A.

Table 10 20 Compounds of the formula I.2, where R3 = hydrogen;
R5 = ethyl;
R4 = in each case one line of Table A.

25 Table 11 Compounds of the formula I.3, where R3 = hydrogen;
R5 = ethyl;
R4 = in each case one line of Table A.
Table 12 Compounds of the formula I.4, where R3 = hydrogen;
R5 = ethyl;
35 R4 = in each case one line of Table A.

Table 13 Compounds of the formula I.l, where R3 = hydrogen;
40 R5 = n-propyl;
R4 = in each case one line of Table A.

Table 14 Compounds of the formula I.2, where 45 R3 = hydrogen;
R5 = n-propyl;

R4 = in each case one line of Table A.

Table 15 Compounds of the formula I.3, where 5 R3 = hydrogen;
R5 = n-propyl;
R4 = in each case one line of Table A.

Table 16 10 Compounds of the formula I.4, where R3 = hydrogen;
R5 = n-propyl;
R4 = in each case one line of Table A.

15 Table 17 Compounds of the formula I.l, where R3 = hydrogen;
Rs = isopropyl;
R4 = in each case one line of Table A.
Table 18 Compounds of the formula I.2, where R3 = hydrogen;
R5 = isopropyl;
25 R4 = in each case one line of Table A.

Table 19 Compounds of the formula I.3, where R3 = hydrogen;
30 R5 = isopropyl;
R4 = in each case one line of Table A.

Table 20 Compounds of the formula I.4, where 35 R3 = hydrogen;
R5 = isopropyl;
R4 = in each case one line of Table A.

Table 21 40 Compounds of the formula I.1, where R3 = hydrogen;
Rs = cyclopropyl;
R4 = in each case one line of Table A.

45 Table 22 Compounds of the formula I.2, where R3 = hydrogen;

R5 = cyc lopropyl;
R4 = in each case one line of Table A.

Table 23 5 Compounds of the formula I.3, where R3 = hydrogen;
R5 = cyclopropyl;
R4 = in each case one line of Table A.

10 Table 24 Compounds of the formula I.4, where R3 = hydrogen;
R5 = cyclopropyl;
R4 = in each case one line of Table A.
Table 25 Compounds of the formula I.l, where R3 = hydrogen;
R5 = n-butyl;
20 R4 = in each case one line of Table A.

Table 26 Compounds of the formula I.2, where R3 = hydrogen;
25 R5 = n-butyl;
R4 = in each case one line of Table A.

Table 27 Compounds of the formula I.3, where 30 R3 = hydrogen;
R5 = n-butyl;
R4 = in each case one line of Table A.

Table 28 35 Compounds of the formula I.4, where R3 = hydrogen;
R5 = n-butyl;
R4 = in each case one line of Table A.

40 Table 29 Compounds of the formula I.l, where R3 = hydrogen;
R5 = 2-methoxyeth-1-yl;
R4 = in each case one line of Table A.
Table 30 Compounds of the formula I.2, where UU~/ ~o~ ~

R3 = hydrogen;
R5 = 2-methoxyeth-1-yl;
R4 = in each case one line of ~able A.

S Table 31 Compounds of the formula I.3, where R3 = hydrogen;
R5 = 2-methoxyeth-1-yl;
R4 = in each case one line of Table A.
Table 32 Compounds of the formula I.4, where R3 = hydrogen;
R5 = 2-methoxyeth-1-yl;
15 R4 = in each case one line of Table A.

Table 33 Compounds of the formula I.1, where R3 = hydrogen;
20 RS = prop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 34 Compounds of the formula I.2, where 25 R3 = hydrogen;
R5 - prop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 35 30 Compounds of the formula I.3, where R3 = hydrogen;
Rs = prop-2-en-1-yl;
R4 = in each case one line of Table A.

35 Table 36 Compounds of the formula I.4, where R3 = hydrogen;
R5 = prop-2-en-1-yl;
R4 = in each case one line of Table A.
Table 37 Compounds of the formula I.1, where R3 = hydrogen;
R5 = E-but-2-en-1-yl;
45 R4 = in each case one line of Table A.

Table 38 Compounds of the formula I.2, where R3 = hydrogen;
R5 = E-but-2-en-1-yl;
5 R4 = in each case one line of Table A.

Table 39 Compounds of the formula I.3, where R3 = hydrogen;
10 R5 = E-but-2-en-1-yl;
R4 = in each case one line of Table A.

Table 40 Compounds of the formula I.4, where 15 R3 = hydrogen;
Rs = E-but-2-en-1-yl;
R4 = in each case one line of Table A.

Table 41 20 Compounds of the formula I.1, where R3 = hydrogen;
R5 = Z-but-2-en-1-yl;
R4 = in each case one line of Table A.

25 Table 42 Compounds of the formula I.2, where R3 = hydrogen;
R5 = Z-but-2-en-1-yl;
R4 = in each case one line of Table A.
Table 43 Compounds of the formula I.3, where R3 = hydrogen;
R5 = Z-but-2-en-1-yl;
35 R4 = in each case one line of Table A.

Table 44 Compounds of the formula I.4, where R3 = hydrogen;
40 Rs = Z-but-2-en-1-yl;
R4 = in each case one line of Table A.

Table 45 Compounds of the formula I.l, where 45 R3 = hydrogen;
R5 = E-3-chloroprop-2-en-1-yl;

R4 = in each case one line of Table A.

Table 46 Compounds of the formula I.2, where 5 R3 = hydrogen;
R5 = E-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 47 10 Compounds of the formula I.3, where R3 = hydrogen;
Rs = E-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

15 Table 48 Compounds of the formula I.4, where R3 = hydrogen;
Rs = E-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.
Table 49 Compounds of the formula I.l, where R3 = hydrogen;
Rs = Z-3-chloroprop-2-en-1-yl;
25 R4 = in each case one line of Table A.

Table 50 Compounds of the formula I.2, where R3 = hydrogen;
30 R5 = Z-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 51 Compounds of the formula I.3, where 35 R3 = hydrogen;
Rs = Z-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 52 40 Compounds of the formula I.4, where R3 = hydrogen;
R5 = Z-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

45 Table 53 Compounds of the formula I.1, where R3 = hydrogen;

R5 = prop-2-yn-1-yl;
R4 = in each case one line of Table A.

Table 54 5 Compounds of the formula I.2, where R3 = hydrogen;
R5 = prop-2-yn-1-yl;
R4 = in each case one line of Table A.

10 Table 55 Compounds of the formula I.3, where R3 = hydrogen;
R5 = prop-2-yn-1-yl;
R4 = in each case one line of Table A.
Table 56 Compounds of the formula I.4, where R3 = hydrogen;
R5 = prop-2-yn-1-yl;
20 R4 = in each case one line of Table A.

Table 57 Compounds of the formula I.1, where R3 = cyclopropyl;
25 R5 = hydrogen;
R4 = in each case one line of Table A.

Table 58 Compounds of the formula I.2, where 30 R3 = cyclopropyl;
R5 = hydrogen;
R4 = in each case one line of Table A.

Table 59 35 Compounds of the formula I.3, where R3 = cyclopropyl;
RS = hydrogen;
R4 = in each case one line of Table A.

40 Table 60 Compounds of the formula I.4, where R3 = cyclopropyl;
Rs = hydrogen;
R4 = in each case one line of Table A.
Table 61 Compounds of the formula I.l, where R3 = cyclopropyl;
R5 = methyl;
R4 = in each case one line of Table A.

5 Table 62 Compounds of the formula I.2, where R3 = cyclopropyl;
R5 = methyl;
R4 = in each case one line of Table A.
Table 63 Compounds of the formula I.3, where R3 = cyclopropyl;
R5 = methyl;
15 R4 = in each case one line of Table A.

Table 64 Compounds of the formula I.4, where R3 = cyclopropyl;
20 R5 = methyl;
R4 = in each case one line of Table A.

Table 65 Compounds of the formula I.1, where 25 R3 = cyclopropyl;
R5 = ethyl;
R4 = in each case one line of Table A.

Table 66 30 Compounds of the formula I.2, where R3 = cyclopropyl;
Rs = ethyl;
R4 = in each case one line of Table A.

35 Table 67 Compounds of the formula I.3, where R3 = cyclopropyl;
R5 = ethyl;
R4 = in each case one line of Table A.
Table 68 Compounds of the formula I.4, where R3 = cyclopropyl;
R5 = ethyl;
45 R4 = in each case one line of Table A.

Table 69 Compounds of the formula I.l, where R3 = cyclopropyl;
R5 = n-propyl;
S R4 = in each case one line of Table A.

Table 70 Compounds of the formula I.2, where R3 = cyclopropyl;
10 R5 = n-propyl;
R4 = in each case one line of Table A.

Table 71 Compounds of the formula I.3, where lS R3 = cyclopropyl;
R5 = n-propyl;
R4 = in each case one line of Table A.

Table 72 20 Compounds of the formula I.4, where R3 = cyclopropyl;
R5 = n-propyl;
R4 = in each case one line of Table A.

25 Table 73 Compounds of the formula I.l, where R3 = cyclopropyl;
R5 = isopropyl;
R4 = in each case one line of Table A.
Table 74 Compounds of the formula I.2, where R3 = cyclopropyl;
R5 = isopropyl;
35 R4 = in each case one line of Table A.

Table 75 Compounds of the formula I.3, where R3 = cyclopropyl;
40 Rs = isopropyl;
R4 = in each case one line of Table A.

Table 76 Compounds of the formula I.4, where 45 R3 = cyclopropyl;
R5 = isopropyl;
., , ' 0050/4627 1 R4 = in each case one line of Table A.

Table 77 Compounds of the formula I.1, where 5 R3 = cyclopropyl;
R5 = cyclopropyl;
R4 = in each case one line of Table A.

Table 78 10 Compounds of the formula I.2, where R3 = cyclopropyl;
R5 = cyclopropyl;
R4 = in each case one line of Table A.

15 Table 79 Compounds of the formula I.3, where R3 = cyclopropyl;
Rs = cyclopropyl;
R4 = in each case one line of Table A.
Table 80 Compounds of the formula I.4, where R3 = cyclopropyl;
R5 = cyclopropyl;
25 R4 = in each case one line of Table A.

Table 81 Compounds of the formula I.l, where R3 = cyclopropyl;
30 R5 = n-butyl;
R4 = in each case one line of Table A.

Table 82 Compounds of the formula I.2, where 35 R3 = cyclopropyl;
R5 = n-butyl;
R4 = in each case one line of Table A.

Table 83 40 Compounds of the formula I.3, where R3 = cyclopropyl;
R5 = n-butyl;
R4 = in each case one line of Table A.

45 Table 84 Compounds of the formula I.4, where R3 = cyclopropyl;

0051~/ 46~7 1 R5 = n-butyl;
R4 = in each case one line o:f Table A.

Table 85 5 Compounds of the formula I.1, where R3 = cyclopropyl;
R5 = 2-methoxyeth-1-yl;
R4 = in each case one line of Table A.

10 Table 86 Compounds of the formula I.2, where R3 = cyclopropyl;
RS = 2-methoxyeth-1-yl;
R4 = in each case one line of Table A.
Table 87 Compounds of the formula I.3, where R3 = cyclopropyl;
R5 = 2-methoxyeth-1-yl;
20 R4 = in each case one line of Table A.

Table 88 Compounds of the formula I.4, where R3 = cyclopropyl;
25 Rs = 2-methoxyeth-1-yl;
R4 = in each case one line of Table A.

Table 89 Compounds of the formula I.1, where 30 R3 = cyclopropyl;
RS = prop-2-en-l-yl;
R4 = in each case one line of Table A.

Table 90 35 Compounds of the formula I.2, where R3 = cyclopropyl;
R5 = prop-2-en-1-yl;
R4 = in each case one line of Table A.

40 Table 91 Compounds of the formula I.3, where R3 = cyclopropyl;
R5 = prop-2-en-1-yl;
R4 = in each case one line of Table A.
Table 92 Compounds of the formula I.4, where R3 = cyclopropyl;
Rs = prop-2-en-1-yl;
R4 = in each case one line of Table A.

5 Table 93 Compounds of the formula I.l, where R3 = cyclopropyl;
R5 = E-but-2-en-1-yl;
R4 = in each case one line of Table A.
Table 94 Compounds of the formula I.2, where R3 = cyclopropyl;
R5 = E-but-2-en-1-yl;
15 R4 = in each case one line of Table A.

Table 95 Compounds of the formula I.3 t where R3 = cyclopropyl;
20 R5 = E-but-2-en-1-yl;
R4 = in each case one line of Table A.

Table 96 Compounds of the formula I.4, where 25 R3 = cyclopropyl;
R5 = E-but-2-en-1-yl;
R4 = in each case one line of Table A.

Table 97 30 Compounds of the formula I.l, where R3 = cyclopropyl;
RS = Z-but-2-en-1-yl;
R4 = in each case one line of Table A.

35 Table 98 Compounds of the formula I.2, where R3 = cyclopropyl;
R5 = Z-but-2-en-1-yl;
R4 = in each case one line of Table A.
Table 99 Compounds of the formula I.3, where R3 = cyclopropyl;
R5 = Z-but-2-en-1-yl;
45 R4 = in each case one line of Table A.

~050/46~71 Table 100 Compounds of the formula I.4, where R3 = cyclopropyl;
R5 = Z-but-2-en-1-yl;
5 R4 = in each case one line of Table A.

Table 101 Compounds of the formula I.1, where R3 = cyclopropyl;
10 R5 = E-3-chloroprop-2-en-1-y.l;
R4 = in each case one line of Table A.

Table 102 Compounds of the formula I.2, where 15 R3 = cyclopropyl;
R5 = E-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 103 20 Compounds of the formula I.3, where R3 = cyclopropyl;
R5 = E-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

25 Table 104 Compounds of the formula I.4, where R3 = cyclopropyl;
R5 = E-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.
Table 105 Compounds of the formula I.1, where R3 = cyclopropyl;
R5 = Z-3-chloroprop-2-en-l-yl;
35 R4 = in each case one line of Table A.

Table 106 Compounds of the formula I.2, where R3 = cyclopropyl;
40 R5 = Z-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 107 Compounds of the formula I.3, where 45 R3 = cyclopropyl;
R5 = Z-3-chloroprop-2-en-1-yl;

R4 = in each case one line of Table A.

Table 108 Compounds of the formula I.4, where S R3 = cyclopropyl;
Rs = Z-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 109 lO Compounds of the formula I.l, where R3 = cyclopropyl;
R5 = prop-2-yn-1-yl;
R4 = in each case one line of Table A.

15 Table 110 Compounds of the formula I.2, where R3 = cyclopropyl;
R5 = prop-2-yn-1-yl;
R4 = in each case one line of Table A.
Table 111 Compounds of the formula I.3, where R3 = cyclopropyl;
R5 = prop-2-yn-1-yl;
25 R4 = in each case one line of Table A.

Table 112 Compounds of the formula I.4, where R3 = cyclopropyl;
30 R5 = prop-2-yn-1-yl;
R4 = in each case one line of Table A.

Table 113 Compounds of the formula I.l~ where 35 R3 = ethyl;
R5 = hydrogen;
R4 = in each case one line of Table A.

Table 114 40 Compounds of the formula I.2, where R3 = ethyl;
R5 = hydrogen;
R4 = in each case one line of Table A.

45 Table 115 Compounds of the formula I.3~ where R3 = ethyl;

R5 = hydrogen R4 = in each case one line of Table A.

Table 116 5 Compounds of the formula I.4, where R3 = ethyl;
Rs = hydrogen;
R4 = in each case one line of Table A.

10 Table 117 Compounds of the formula I.l, where R3 = ethyl;
R5 = methyl;
R4 = in each case one line of Table A.
Table 118 Compounds of the formula I.2, where R3 = ethyl;
R5 = methyl;
20 R4 = in each case one line of Table A.

Table 119 Compounds of the formula I.3, where R3 = ethyl;
25 R5 = methyl;
R4 = in each case one line of Table A.

Table 120 Compounds of the formula I.4, where 30 R3 = ethyl;
Rs = methyl;
R4 = in each case one line of Table A.

Table 121 35 Compounds of the formula I.1, where R3 = ethyl;
R5 = ethyl;
R4 = in each case one line of Table A.

40 Table 122 Compounds of the formula I.2, where R3 = ethyl;
R5 = ethyl;
R4 = in each case one line of Table A.
Table 123 Compounds of the formula I.3, where OOSO/46i!7 1 R3 = ethyl;
R5 = ethyl;
R4 = in each case one line of Table A.

5 Table 124 Compounds of the formula I.4, where R3 = ethyl;
R5 = ethyl;
R4 = in each case one line of Table A.
Table 125 Compounds of the formula I.l, where R3 = ethyl;
R5 = n-propyl;
15 R4 = in each case one line of Table A.

Table 126 Compounds of the formula I.2, where R3 = ethyl;
20 R5 = n-propyl;
R4 = in each case one line of Table A.

Table 127 Compounds of the formula I.3, where 25 R3 = ethyl;
R5 = n-propyl;
R4 = in each case one line of Table A.

Table 128 30 Compounds of the formula I.4, where R3 = ethyl;
R5 = n-propyl;
R4 = in each case one line of Table A.

35 Table 129 Compounds of the formula I.1, where R3 = ethyl;
R5 = isopropyl;
R4 = in each case one line of Table A.
Table 130 Compounds of the formula I.2, where R3 = ethyl;
R5 = isopropyl;
45 R4 = in each case one line of Table A.

Table 131 Compounds of the formula I.3, where R3 = ethyl;
R5 = isopropyl;
5 R4 = in each case one line of Table A.

Table 132 Compounds of the formula I.4, where R3 = ethyl;
lO R5 = isopropyl;
R4 = in each case one line of Table A.

Table 133 Compounds of the formula I.1, where 15 R3 = ethyl;
R5 = cyclopropyl;
R4 = in each case one line of Table A.

Table 134 20 Compounds of the formula I.2, where R3 = ethyl;
R5 = cyclopropyl;
R4 = in each case one line of Table A.

25 Table 135 Compounds of the formula I.3, where R3 = ethyl;
R5 = cyclopropyl;
R4 = in each case one line of Table A.
Table 136 Compounds of the formula I.4, where R3 = ethyl;
R5 = cyclopropyl;
35 R4 = in each case one line of Table A.

Table 137 Compounds of the formula I.l, where R3 = ethyl;
40 R5 = n-butyl;
R4 = in each case one line of Table A.

Table 138 Compounds of the formula I.2, where 45 R3 = ethyl;
R5 = n-butyl;

0050~ 4627 1 R4 = in each case one line of Table A.

Table 139 Compounds of the formula I.3, where 5 R3 = ethyl;
R5 = n-butyl;
R4 = in each case one line of Table A.

Table 140 lO Compounds of the formula I.4, where R3 = ethyl;
R5 = n-butyl;
R4 = in each case one line of Table A.

15 Table 141 Compounds of the formula I.1, where R3 = ethyl;
Rs = 2-methoxyeth-1-yl;
R4 = in each case one line of Table A.
Table 142 Compounds of the formula I.2, where R3 = ethyl;
R5 = 2-methoxyeth-1-yl;
25 R4 = in each case one line of Table A.

Table 143 Compounds of the formula I.3, where R3 = ethyl;
30 R5 = 2-methoxyeth-1-yl;
R4 = in each case one line of Table A.

Table 144 Compounds of the formula I.4, where 35 R3 = ethyl;
R5 = 2-methoxyeth-1-yl;
R4 = in each case one line of Table A.

Table 145 40 Compounds of the formula I.l, where R3 = ethyl;
RS = prop-2-en-1-yl;
R4 = in each case one line of Table A.

45 Table 146 Compounds of the formula I.2, where R3 = ethyl;

OOSO/ 4~Z7 1 R5 = prop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 147 5 Compounds of the formula I.3, where R3 = ethyl;
R5 = prop-2-en-1-yl;
R4 = in each case one line of Table A.

10 Table 148 Compounds of the formula I.4, where R3 = ethyl;
R5 = prop-2-en-1-yl;
R4 = in each case one line of Table A.
Table 149 Compounds of the formula I.l, where R3 = ethyl;
Rs = E-but-2-en-1-yl;
20 R4 = in each case one line of Table A.

Table 150 Compounds of the formula I.2, where R3 = ethyl;
25 Rs = E-but-2-en-1-yl;
R4 = in each case one line of Table A.

Table 151 Compounds of the formula I.3, where 30 R3 = ethyl;
R5 = E-but-2-en-1-yl;
R4 = in each case one line of Table A.

Table 152 35 Compounds of the formula I.4, where R3 = ethyl;
R5 = E-but-2-en-1-yl;
R4 = in each case one line of Table A.

40 Table 153 Compounds of the formula I.l, where R3 = ethyl;
R5 = Z-but-2-en-1-yl;
R4 = in each case one line of Table A.
Table 154 Compounds of the formula I.2, where R3 = ethyl;
R5 = Z-but-2-en-l-yl;
R4 = in each case one line of Table A.

5 Table 155 Compounds of the formula I.3, where R3 = ethyl;
R5 = Z-but-2-en-1-yl;
R4 = in each case one line of Table A.
Table 156 Compounds of the formula I.4, where R3 = ethyl;
R5 = Z-but-2-en-1-yl;
15 R4 = in each case one line of Table A.

Table 157 Compounds of the formula I.l, where R3 = ethyl;
20 R5 = E-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 158 Compounds of the formula I.2, where 25 R3 = ethyl;
Rs = E-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 159 30 Compounds of the formula I.3 t where R3 = ethyl;
R5 = E-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

35 Table 160 Compounds of the formula I.4, where R3 = ethyl;
R5 = E-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.
Table 161 Compounds of the formula I.l, where R3 = ethyl;
R5 = Z- 3-chloroprop-2-en-1-yl;
45 R4 = in each case one line of Table A.

CA 0223l66l l998-04-07 Table 162 Compounds of the formula I.2, where R3 = ethyl;
R5 = Z-3-chloroprop-2-en-1-y:l;
5 R4 = in each case one line of Table A.

Table 163 Compounds of the formula I.3, where R3 = ethyl;
10 R5 = Z-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 164 Compounds of the formula I.4, where 15 R3 = ethyl;
R5 = Z-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 165 20 Compounds of the formula I.l, where R3 = ethyl;
R5 = prop-2-yn-1-yl;
R4 = in each case one line of Table A.

25 Table 166 Compounds of the formula I.2, where R3 = ethyl;
R5 = prop-2-yn-1-yl;
R4 = in each case one line of Table A.
Table 167 Compounds of the formula I.3, where R3 = ethyl;
R5 = prop-2-yn-1-yl;
35 R4 = in each case one line of Table A.

Table 168 Compounds of the formula I.4, where R3 = ethyl;
40 R5 = prop-2-yn-1-yl;
R4 = in each case one line of Table A.

Table 169 Compounds of the formula I.l, where 45 R3 = trifluoromethyl;
R5 = hydrogen;

005U/ 4t~7 1 R4 = in each case one line of Table A.

Table 170 Compounds of the formula I.2, where 5 R3 = trifluoromethyl;
R5 = hydrogen;
R4 = in each case one line of Table A.

Table 171 10 Compounds of the formula I.:3, where R3 = trifluoromethyl;
R5 = hydrogen;
R4 = in each case one line of Table A.

15 Table 172 Compounds of the formula I.4, where R3 = trifluoromethyl;
R5 = hydrogen;
R4 = in each case one line of Table A.
Table 173 Compounds of the formula I.l, where R3 = trifluoromethyl;
R5 = methyl;
25 R4 = in each case one line of Table A.

Table 174 Compounds of the formula I.2, where R3 = trifluoromethyl;
30 R5 = methyl;
R4 = in each case one line of Table A.

Table 175 Compounds of the formula I.3, where 35 R3 = trifluoromethyl;
R5 = methyl;
R4 = in each case one line of Table A.

Table 176 40 Compounds of the formula I.4, where R3 = trifluoromethyl;
R5 = methyl;
R4 = in each case one line of Table A.

45 Table 177 Compounds of the formula I.l, where R3 = trifluoromethyl;

UU:~U/ 4~

R5 = ethyl;
R4 = in each case one line of Table A.

Table 178 5 Compounds of the formula I.2, where R3 = trifluoromethyl;
R5 = ethyl;
R4 = in each case one line of Table A.

10 Table 179 Compounds of the formula I.3, where R3 = trifluoromethyl;
R5 = ethyl;
R4 = in each case one line of Table A.
Table 180 Compounds of the formula I.4, where R3 = trifluoromethyl;
R5 = ethyl;
20 R4 = in each case one line of Table A.

Table 181 Compounds of the formula I.1, where R3 = trifluoromethyl;
25 R5 = n-propyl;
R4 = in each case one line of Table A.

Table 182 Compounds of the formula I.2, where 30 R3 = trifluoromethyl;
R5 = n-propyl;
R4 = in each case one line of Table A.

Table 183 35 Compounds of the formula I.3, where R3 = trifluoromethyl;
R5 = n-propyl;
R4 = in each case one line of Table A.

40 Table 184 Compounds of the formula I.4, where R3 = trifluoromethyl;
R5 = n-propyl;
R4 = in each case one line of Table A.
Table 185 Compounds of the formula I.l, where 0~51~/ 4~7 1 R3 = trifluoromethyl;
R5 = isopropyl;
R4 = in each case one line of Table A.

S Table 186 Compounds of the formula I.2, where R3 = trifluoromethyl;
R5 = isopropyl;
R4 = in each case one line of Table A.
Table 187 Compounds of the formula I.3, where R3 = trifluoromethyl;
R5 = isopropyl;
15 R4 = in each case one line of Table A.

Table 188 Compounds of the formula I.4, where R3 = trifluoromethyl;
20 R5 = isopropyl;
R4 = in each case one line of Table A.

Table 189 Compounds of the formula I.l, where 25 R3 = trifluoromethyl;
R5 = cyclopropyl;
R4 = in each case one line of Table A.

Table 190 30 Compounds of the formula I.2, where R3 = trifluoromethyl;
Rs = cyclopropyl;
R4 = in each case one line of Table A.

35 Table 191 Compounds of the formula I.3, where R3 = trifluoromethyl;
R5 = cyclopropyl;
R4 = in each case one line of Table A.
Table 192 Compounds of the formula I.4, where R3 = trifluoromethyl;
R5 = cyclopropyl;
45 R4 = in each case one line of Table A.

Table 193 Compounds of the formula I.1, where R3 = trifluoromethyl;
R5 = n-butyl;
5 R4 = in each case one line of Table A.

Table 194 Compounds of the formula I.2, where R3 = trifluoromethyl;
lO RS = n-butyl;
R4 = in each case one line of Table A.

Table 195 Compounds of the formula I.3, where 15 R3 = trifluoromethyl;
R5 = n-butyl;
R4 = in each case one line of Table A.

Table 196 20 Compounds of the formula I.4, where R3 = trifluoromethyl;
R5 = n-butyl;
R4 = in each case one line of Table A.

25 Table 197 Compounds of the formula I.1, where R3 = trifluoromethyl;
R5 = 2-methoxyeth-1-yl;
R4 = in each case one line of Table A.
Table 198 Compounds of the formula I.2, where R3 = trifluoromethyl;
R5 = 2-methoxyeth-1-yl;
35 R4 = in each case one line of Table A.

Table 199 Compounds of the formula I.3, where R3 = trifluoromethyl;
40 R5 = 2-methoxyeth-1-yl;
R4 = in each case one line of Table A.

Table 200 Compounds of the formula I.4, where 45 R3 = trifluoromethyl;
R5 = 2-methoxyeth-1-yl;

CA 0223l66l l998-04-07 UU~U/4~

R4 = in each case one line of Table A.

Table 201 Compounds of the formula I.1, where 5 R3 = trifluoromethyl;
R5 = prop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 202 10 Compounds of the formula I.2, where R3 = trifluoromethyl;
R5 = prop-2-en-1-yl;
R4 = in each case one line of Table A.

15 Table 203 Compounds of the formula I.3, where R3 = trifluoromethyl;
R5 = prop-2-en-1-yl;
R4 = in each case one line of Table A.
Table 204 Compounds of the formula I.4, where R3 = trifluoromethyl;
R5 = prop-2-en-1-yl;
25 R4 = in each case one line of Table A.

Table 205 Compounds of the formula I.1, where R3 = trifluoromethyl;
30 R5 = E-but-2-en-1-yl;
R4 = in each case one line of Table A.

Table 206 Compounds of the formula I.2, where 35 R3 = trifluoromethyl;
R5 = E-but-2-en-1-yl;
R4 = in each case one line of Table A.

Table 207 40 Compounds of the formula I.3, where R3 = trifluoromethyl;
R5 = E-but-2-en-1-yl;
R4 = in each case one line of Table A.

45 Table 208 Compounds of the formula I.4, where R3 = trifluoromethyl;

~U:~U/ 4t~7 1 Rs = E-but-2-en-1-yl;
R4 = in each case one line of Table A.

Table 209 5 Compounds of the formula I.1, where R3 = trifluoromethyl;
Rs = Z-but-2-en-1-yl;
R4 = in each case one line of Table A.

10 Table 210 Compounds of the formula I.2, where R3 = trifluoromethyl;
R5 = Z-but-2-en-1-yl;
R4 = in each case one line of Table A.
Table 211 Compounds of the formula I.3, where R3 = trifluoromethyl;
R5 = Z-but-2-en-1-yl;
20 R4 = in each case one line of Table A.

Table 212 Compounds of the formula I.4, where R3 = trifluoromethyl;
25 R5 = Z-but-2-en-1-yl;
R4 = in each case one line of Table A.

Table 213 Compounds of the formula I.l, where 30 R3 = trifluoromethyl;
R5 = E-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 214 35 Compounds of the formula I.2, where R3 = trifluoromethyl;
R5 = E-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

40 Table 215 Compounds of the formula I.3, where R3 = trifluoromethyl;
R5 = E-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.
Table 216 Compounds of the formula I.4, where R3 = trifluoromethyl;
R5 = E-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

5 Table 217 Compounds of the formula I.l, where R3 = trifluoromethyl;
R5 = Z-3-chloroprop-2-en-1-y:L;
R4 = in each case one line of Table A.
Table 218 Compounds of the formula I.2, where R3 = trifluoromethyl;
R5 = Z-3-chloroprop-2-en-1-y:L;
15 R4 = in each case one line of Table A.

Table 219 Compounds of the formula I.3, where R3 = trifluoromethyl;
20 R5 = Z-3-chloroprop-2-en-1-y:L;
R4 = in each case one line of Table A.

Table 220 Compounds of the formula I.4, where 25 R3 = trifluoromethyl;
R5 = Z-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 221 30 Compounds of the formula I.l, where R3 = trifluoromethyl;
R5 = prop-2-yn-1-yl;
R4 = in each case one line of Table A.

35 Table 222 Compounds of the formula I.2, where R3 = trifluoromethyl;
R5 = prop-2-yn-1-yl;
R4 = in each case one line of Table A.
Table 223 Compounds of the formula I.3, where R3 = trifluoromethyl;
R5 = prop-2-yn-1-yl;
45 R4 = in each case one line of Table A.

Table 224 Compounds of the formula I.4, where R3 = trifluoromethyl;
S R5 = prop-2-yn-1-yl;
R4 = in each case one line o:E Table A.

Table 225 Compounds of the formula I.1, where 10 R3 = methyl;
R5 = hydrogen;
R4 = in each case one line of Table A.

Table 226 15 Compounds of the formula I.2, where R3 = methyl;
R5 = hydrogen;
R4 = in each case one line of Table A.

20 Table 227 Compounds of the formula I.3, where R3 = methyl;
R5 = hydrogen;
R4 = in each case one line o:E Table A.
Table 228 Compounds of the formula I.4, where R3 = methyl;
R5 = hydrogen;
30 R4 = in each case one line of Table A.

Table 229 Compounds of the formula I.1, where R3 = methyl;
35 R5 = methyl;
R4 = in each case one line of Table A.

Table 230 Compounds of the formula I.2, where 40 R3 = methyl;
R5 = methyl;
R4 = in each case one line of Table A.

Table 231 45 Compounds of the formula I.3, where R3 = methyl;
R5 = methyl;

R4 = in each case one line of Table A.

Table 232 Compounds of the formula I.4, where S R3 = methyl;
R5 = methyl;
R4 = in each case one line of Table A.

Table 233 10 Compounds of the formula I.l, where R3 = methyl;
R5 = ethyl;
R4 = in each case one line of Table A.

15 Table 234 Compounds of the formula I.2, where R3 = methyl;
R5 = ethyl;
R4 = in each case one line of Table A.
Table 235 Compounds of the formula I.3, where R3 = methyl;
R5 = ethyl;
25 R4 = in each case one line of Table A.

Table 236 Compounds of the formula I.4, where R3 = methyl;
30 R5 = ethyl;
R4 = in each case one line of Table A.

Table 237 Compounds of the formula I.1, where 35 R3 = methyl;
R5 = n-propyl;
R4 = in each case one line of Table A.

Table 238 40 Compounds of the formula I.2, where R3 = methyl;
R5 = n-propyl;
R4 = in each case one line of Table A.

45 Table 239 Compounds of the formula I.3, where R3 = methyl;

R5 = n-propyl;
R4 = in each case one line of Table A.

Table 240 5 Compounds of the formula I.4, where R3 = methyl;
R5 = n-propyl;
R4 = in each case one line of Table A.

10 Table 241 Compounds of the formula I.1, where R3 = methyl;
Rs = isopropyl;
R4 = in each case one line of Table A.
Table 242 Compounds of the formula I.2, where R3 = methyl;
R5 = isopropyl;
20 R4 = in each case one line of Table A.

Table 243 Compounds of the formula I.3, where R3 = methyl;
25 RS = isopropyl;
R4 = in each case one line of Table A.

Table 244 Compounds of the formula I.4, where 30 R3 = methyl;
R5 = isopropyl;
R4 = in each case one line of Table A.

Table 245 35 Compounds of the formula I.1, where R3 = methyl;
R5 = cyclopropyl;
R4 = in each case one line of Table A.

40 Table 246 Compounds of the formula I.2, where R3 = methyl;
R5 = cyclopropyl;
R4 = in each case one line oi- Table A.
Table 247 Compounds of the formula I.3, where R3 = methyl;
R5 = cyclopropyl;
R4 = in each case one line of Table A.

5 Table 248 Compounds of the formula I.4, where R3 = methyl;
Rs = cyclopropyl;
R4 = in each case one line o:f Table A.
Table 249 Compounds of the formula I.1, where R3 = methyl;
R5 = n-butyl;
15 R4 = in each case one line of Table A.

Table 250 Compounds of the formula I.2, where R3 = methyl;
20 R5 = n-butyl;
R4 = in each case one line of Table A.

Table 251 Compounds of the formula I.3, where 25 R3 = methyl;
R5 = n-butyl;
R4 = in each case one line of Table A.

Table 252 30 Compounds of the formula I.4, where R3 = methyl;
Rs = n-butyl;
R4 = in each case one line of Table A.

35 Table 253 Compounds of the formula I.1, where R3 = methyl;
Rs = 2-methoxyeth-1-yl;
R4 = in each case one line of Table A.
Table 254 Compounds of the formula I.2, where R3 = methyl;
R5 = 2-methoxyeth-1-yl;
45 R4 = in each case one line of Table A.

Table 255 Compounds of the formula I.3, where R3 = methyl;
R5 = 2-methoxyeth-1-yl;
5 R4 = in each case one line of Table A.

Table 256 Compounds of the formula I.4, where R3 = methyl;
10 R5 = 2-methoxyeth-1-yl;
R4 = in each case one line of Table A.

Table 257 Compounds of the formula I.l, where 15 R3 = methyl;
R5 = prop-2-en-1-yl;
R4 = in each case one line of. Table A.

Table 258 20 Compounds of the formula I.2, where R3 = methyl;
R5 = prop-2-en-1-yl;
R4 = in each case one line of Table A.

25 Table 259 Compounds of the formula I.3 r where R3 = methyl;
R5 = prop-2-en-1-yl;
R4 = in each case one line of Table A.
Table 260 Compounds of the formula I.4, where R3 = methyl;
R5 = prop-2-en-1-yl;
35 R4 = in each case one line of Table A.

Table 261 Compounds of the formula I.l, where R3 = methyl;
40 R5 = E-but-2-en-1-yl;
R4 = in each case one line of Table A.

Table 262 Compounds of the formula I.2, where 45 R3 = methyl;
R5 = E-but-2-en-1-yl;

R4 = in each case one line of Table A.

Table 263 Compounds of the formula I.3, where 5 R3 = methyl;
Rs = E-but-2-en-1-yl;
R4 = in each case one line of Table A.

Table 264 10 Compounds of the formula I.4, where R3 = methyl;
R5 = E-but-2-en-1-yl;
R4 = in each case one line of Table A.

15 Table 265 Compounds of the formula I.l, where R3 = methyl;
R5 = Z-but-2-en-1-yl;
R4 = in each case one line of Table A.
Table 266 Compounds of the formula I.2, where R3 = methyl;
Rs = Z-but-2-en-1-yl;
25 R4 = in each case one line of Table A.

Table 267 Compounds of the formula I.3, where R3 = methyl;
30 R5 = Z-but-2-en-1-yl;
R4 = in each case one line of Table A.

Table 268 Compounds of the formula I.4, where 35 R3 = methyl;
Rs = Z-but-2-en-1-yl;
R4 = in each case one line of Table A.

Table 269 40 Compounds of the formula I.1, where R3 = methyl;
Rs = E-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

45 Table 270 Compounds of the formula I.2, where R3 = methyl;

R5 = E-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 271 5 Compounds of the formula I.3, where R3 = methyl;
R5 = E-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

10 Table 272 Compounds of the formula I.4, where R3 = methyl;
R5 = E-3-chloroprop-2-en-1-y.l;
R4 = in each case one line of Table A.
Table 273 Compounds of the formula I.1, where R3 = methyl;
R5 = Z-3-chloroprop-2-en-1-yl;
20 R4 = in each case one line of Table A.

Table 274 Compounds of the formula I.2, where R3 = methyl;
25 R5 = Z-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 275 Compounds of the formula I.3, where 30 R3 = methyl;
R5 = Z-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 276 35 Compounds of the formula I.4, where R3 = methyl;
R5 = Z-3-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

40 Table 277 Compounds of the formula I.1, where R3 = methyl;
R5 = prop-2-yn-1-yl;
R4 = in each case one line of Table A.
Table 278 Compounds of the formula I.2, where R3 = methyl;
R5 = prop-2-yn-1-yl;
R4 = in each case one line of Table A.

5 Table 279 Compounds of the formula I.3, where R3 = methyl;
R5 = prop-2-yn-1-yl;
R4 = in each case one line of Table A.
Table 280 Compounds of the formula I.4, where R3 = methyl;
R5 = prop-2-yn-1-yl;
15 R4 = in each case one line of Table A.

Table 281 Compounds of the formula I.1, where R3 = methyl;
20 R5 = 2-butyl;
R4 = in each case one line of Table A.

Table 282 Compounds of the formula I.2, where 25 R3 = methyl;
R5 = 2-butyl;
R4 = in each case one line of Table A.

Table 283 30 Compounds of the formula I.3, where R3 = methyl;
R5 = 2-butyl;
R4 = in each case one line of Table A.

35 Table 284 Compounds of the formula I.4, where R3 = methyl;
R5 = 2-butyl;
R4 = in each case one line of Table A.
Table 285 Compounds of the formula I.l, where R3 = methyl;
R5 = 2-methylprop-1-yl;
45 R4 = in each case one line of Table A.

Table 286 Compounds of the formula I.2, where R3 = methyl;
R5 = 2-methylprop-l-yl;
5 R4 = in each case one line of Table A.

Table 287 Compounds of the formula I.3,. where R3 = methyl;
10 R5 = 2-methylprop-1-yl;
R4 = in each case one line of Table A.

Table 288 Compounds of the formula I.4, where 15 R3 = methyl;
R5 = 2-methylprop-1-yl;
R4 = in each case one line of Table A.

Table 289 20 Compounds of the formula I.l r where R3 = methyl;
R5 = l,l-dimethyleth-l-yl;
R4 = in each case one line of Table A.

25 Table 290 Compounds of the formula I.2, where R3 = methyl;
R5 = l,l-dimethyleth-l-yl;
R4 = in each case one line of Table A.
Table 291 Compounds of the formula I.3, where R3 = methyl;
R5 = 1,1-dimethyleth-1-yl;
35 R4 = in each case one line of Table A.

Table 292 Compounds of the formula I.4, where R3 = methyl;
40 R5 = l,l-dimethyleth-l-yl;
R4 = in each case one line of Table A.

Table 293 Compounds of the formula I.l, where 45 R3 = methyl;
R5 = l-pentyl;

R4 = in each case one line of Table A.

Table 294 Compounds of the formula I.2, where 5 R3 = methyl;
Rs = 1-pentyl;
R4 = in each case one line of Table A.

Table 295 10 Compounds of the formula I.3, where R3 = methyl;
R5 = 1-pentyl;
R4 = in each case one line of Table A.

15 Table 296 Compounds of the formula I.4, where R3 = methyl;
R5 = 1-pentyl;
R4 = in each case one line of Table A.

Table 297 Compounds of the formula I.1, where R3 = methyl;
R5 = 3-methylbut-1-yl;
25 R4 = in each case one line of Table A.

Table 298 Compounds of the formula I.2, where R3 = methyl;
30 R5 = 3-methylbut-1-yl;
R4 = in each case one line of Table A.

Table 299 Compounds of the formula I.3, where 35 R3 = methyl;
R5 = 3-methylbut-1-yl;
R4 = in each case one line of Table A.

Table 300 40 Compounds of the formula I.4, where R3 = methyl;
R5 = 3-methylbut-1-yl;
R4 = in each case one line of Table A.

45 Table 301 Compounds of the formula I.1, where R3 = methyl;

R5 = 2,2-dimethylprop-1-yl;
R4 = in each case one line of Table A.

Table 302 5 Compounds of the formula I.2, where R3 = methyl;
R5 = 2,2-dimethylprop-1-yl;
R4 = in each case one line of Table A.

10 Table 303 Compounds of the formula I.3, where R3 = methyl;
R5 = 2,2-dimethylprop-1-yl;
R4 = in each case one line of Table A.
Table 304 Compounds of the formula I.4, where R3 = methyl;
R5 = 2,2-dimethylprop-1-yl;
20 R4 = in each case one line of Table A.

Table 305 Compounds of the formula I.1, where R3 = methyl;
25 R5 = 2-methylbut-1-yl;
R4 = in each case one line of Table A.

Table 306 Compounds of the formula I.2, where 30 R3 = methyl;
R5 = 2-methylbut-1-yl;
R4 = in each case one line of Table A.

Table 307 35 Compounds of the formula I.3, where R3 = methyl;
R5 = 2-methylbut-1-yl;
R4 = in each case one line of Table A.

40 Table 308 Compounds of the formula I.4, where R3 = methyl;
R5 = 2-methylbut-1-yl;
R4 = in each case one line of Table A.
Table 309 Compounds of the formula I.1, where CA 0223l66l l998-04-07 R3 = methyl;
R5 = l-methylbut-1-yl;
R4 = in each case one line of Table A.

5 Table 310 Compounds of the formula I.2, where R3 = methyl;
R5 = l-methylbut-l-yl;
R4 = in each case one line of Table A.
Table 311 Compounds of the formula I.3, where R3 = methyl;
RS = 1-methylbut-1-yl;
15 R4 = in each case one line of Table A.

Table 312 Compounds of the formula I.4, where R3 = methyl;
20 R5 = 1-methylbut-1-yl;
R4 = in each case one line of Table A.

Table 313 Compounds of the formula I.1, where 25 R3 = methyl;
R5 = 3-pentyl;
R4 = in each case one line of Table A.

Table 314 30 Compounds of the formula I.2, where R3 = methyl;
R5 = 3-pentyl;
R4 = in each case one line of Table A.

35 Table 315 Compounds of the formula I.3, where R3 = methyl;
R5 = 3-pentyl;
R4 = in each case one line of Table A.
Table 316 Compounds of the formula I.4, where R3 = methyl;
R5 = 3-pentyl;
45 R4 = in each case one line of Table A.

Table 317 Compounds of the formula I.1, where R3 = methyl;
Rs = 3-methylbut-2-yl;
5 R4 = in each case one line of Table A.

Table 318 Compounds of the formula I.2, where R3 = methyl;
10 R5 = 3-methylbut-2-yl;
R4 = in each case one line of Table A.

Table 319 Compounds of the formula I.3, where lS R3 = methyl;
R5 = 3-methylbut-2-yl;
R4 = in each case one line of Table A.

Table 320 20 Compounds of the formula I.4, where R3 = methyl;
Rs = 3-methylbut-2-yl;
R4 = in each case one line of Table A.

25 Table 321 Compounds of the formula I.1, where R3 = methyl;
R5 = 2-methylbut-2-yl;
R4 = in each case one line of Table A.
Table 322 Compounds of the formula I.2, where R3 = methyl;
R5 = 2-methylbut-2-yl;
35 R4 = in each case one line of Table A.

Table 323 Compounds of the formula I.3, where R3 = methyl;
40 R5 = 2-methylbut-2-yl;
R4 = in each case one line of Table A.

Table 324 Compounds of the formula I.4, where 45 R3 = methyl;
R5 = 2-methylbut-2-yl;

R4 = in each case one line of Table A.

Table 325 Compounds of the formula I.1, where 5 R3 = methyl;
R5 = l-hexyl;
R4 = in each case one line of Table A.

Table 326 10 Compounds of the formula I.2, where R3 = methyl;
Rs = l-hexyl;
R4 = in each case one line of Table A.

15 Table 327 Compounds of the formula I.3, where R3 = methyl;
R5 = 1-hexyl;
R4 = in each case one line of Table A.
Table 328 Compounds of the formula I.4, where R3 = methyl;
R5 = 1-hexyl;
25 R4 = in each case one line of Table A.

Table 329 Compounds of the formula I.l, where R3 = methyl;
30 Rs = 3,3-dimethylbut-1-yl;
R4 = in each case one line of Table A.

Table 330 Compounds of the formula I.2, where 35 R3 = methyl;
R5 = 3,3-dimethylbut-1-yl;
R4 = in each case one line of Table A.

Table 331 40 Compounds of the formula I.3, where R3 = methyl;
R5 = 3,3-dimethylbut-1-yl;
R4 = in each case one line of Table A.

45 Table 332 Compounds of the formula I.4, where R3 = methyl;

R5 = 3,3-dimethylbut-1-yl;
R4 = in each case one line of Table A.

Table 333 5 Compounds of the formula I.1, where R3 = methyl;
R5 = 2-ethylbut-1-yl;
R4 = in each case one line of Table A.

10 Table 334 Compounds of the formula I.2, where R3 = methyl;
R5 = 2-ethylbut-1-yl;
R4 = in each case one line of Table A.
Table 335 Compounds of the formula I.3, where R3 = methyl;
R5 = 2-ethylbut-1-yl;
20 R4 = in each case one line of Table A.

Table 336 Compounds of the formula I.4, where R3 = methyl;
25 R5 = 2-ethylbut-1-yl;
R4 = in each case one line of Table A.

Table 337 Compounds of the formula I.1, where 30 R3 = methyl;
R5 = l-ethylbut-1-yl;
R4 = in each case one line of Table A.

Table 338 35 Compounds of the formula I.2, where R3 = methyl;
R5 = 1-ethylbut-1-yl;
R4 = in each case one line of Table A.

40 Table 339 Compounds of the formula I.3, where R3 = methyl;
R5 = l-ethylbut-1-yl;
R4 = in each case one line of Table A.
Table 340 Compounds of the formula I.4, where R3 = methyl;
R5 = l-ethylbut-l-yl;
R4 = in each case one line of Table A.

5 Table 341 Compounds of the formula I.l r where R3 = methyl;
R5 = 4-methylpent-1-yl;
R4 = in each case one line of Table A.
Table 342 Compounds of the formula I.2, where R3 = methyl;
R5 = 4-methylpent-1-yl;
15 R4 = in each case one line of Table A.

Table 343 Compounds of the formula I.3, where R3 = methyl;
20 R5 = 4-methylpent-1-yl;
R4 = in each case one line of Table A.

Table 344 Compounds of the formula I.4 t where 25 R3 = methyl;
R5 = 4-methylpent-1-yl;
R4 = in each case one line of Table A.

Table 345 30 Compounds of the formula I.l,. where R3 = methyl;
R5 = cyclopropylmethyl;
R4 = in each case one line of Table A.

35 Table 346 Compounds of the formula I.2, where R3 = methyl;
RS = cyclopropylmethyl;
R4 = in each case one line of Table A.
Table 347 Compounds of the formula I.3, where R3 = methyl;
R5 = cyclopropylmethyl;
45 R4 = in each case one line of Table A.

Table 348 Compounds of the formula I.4, where R3 = methyl;
R5 = cyclopropylmethyl;
5 R4 = in each case one line of Table A.

Table 349 Compounds of the formula I.l, where R3 = methyl;
10 Rs = cyclopentylmethyl;
R4 = in each case one line of Table A.

Table 350 Compounds of the formula I.2, where 15 R3 = methyl;
RS = cyclopentylmethyl;
R4 = in each case one line of Table A.

Table 351 20 Compounds of the formula I.3, where R3 = methyl;
Rs = cyclopentylmethyl;
R4 = in each case one line of Table A.

25 Table 352 Compounds of the formula I.4, where R3 = methyl;
R5 = cyclopentylmethyl;
R4 = in each case one line of Table A.
Table 353 Compounds of the formula I.l/ where R3 = methyl;
Rs = 2-cyclopropyleth-1-yl;
35 R4 = in each case one line of Table A.

Table 354 Compounds of the formula I.2, where R3 = methyl;
40 Rs = 2-cyclopropyleth-1-yl;
R4 = in each case one line of Table A.

Table 355 Compounds of the formula I.3, where 45 R3 = methyl;
R5 = 2-cyclopropyleth-1-yl;

OOSO/4627~

R4 = in each case one line of Table A.

Table 356 Compounds of the formula I.4, where 5 R3 = methyl;
R5 = 2-cyclopropyleth-1-yl;
R4 = in each case one line of Table A.

Table 357 10 Compounds of the formula I.l, where R3 = methyl;
Rs = 2-cyclopentyleth-1-yl;
R4 = in each case one line of Table A.

15 Table 358 Compounds of the formula I.2, where R3 = methyl;
R5 = 2-cyclopentyleth-1-yl;
R4 = in each case one line of Table A.
Table 359 Compounds of the formula I.3, where R3 = methyl;
R5 = 2-cyclopentyleth-1-yl;
25 R4 = in each case one line of Table A.

Table 360 Compounds of the formula I.4, where R3 = methyl;
30 R5 = 2-cyclopentyleth-1-yl;
R4 = in each case one line of Table A.

Table 361 Compounds of the formula I.1, where 35 R3 = methyl;
R5 = 2-cyclohexyleth-1-yl;
R4 = in each case one line of Table A.

Table 362 40 Compounds of the formula I.2, where R3 = methyl;
R5 = 2-cyclohexyleth-1-yl;
R4 = in each case one line of Table A.

45 Table 363 Compounds of the formula I.3 r where R3 = methyl;

R5 = 2-cyclohexyleth-1-yl;
R4 = in each case one line of Table A.

Table 364 5 Compounds of the formula I.4, where R3 = methyl;
R5 = 2-cyclohexyleth-1-yl;
R4 = in each case one line of Table A.

10 Table 365 Compounds of the formula I.1, where R3 = methyl;
R5 = fluoromethyl;
R4 = in each case one line of Table A.
Table 366 Compounds of the formula I.2, where R3 = methyl;
R5 = fluoromethyl;
20 R4 = in each case one line of Table A.

Table 367 Compounds of the formula I.3, where R3 = methyl;
25 R5 = fluoromethyl;
R4 = in each case one line of Table A.

Table 368 Compounds of the formula I.4, where 30 R3 = methyl;
Rs = fluoromethyl;
R4 = in each case one line of Table A.

Table 369 35 Compounds of the formula I.l, where R3 = methyl;
Rs = difluoromethyl;
R4 = in each case one line of Table A.

40 Table 370 Compounds of the formula I.2, where R3 = methyl;
R5 = difluoromethyl;
R4 = in each case one line of Table A.
Table 371 Compounds of the formula I.3, where R3 = methyl;
R5 = difluoromethyl;
R4 = in each case one line of Table A.

5 Table 372 Compounds of the formula I.4, where R3 = methyl;
R5 = difluoromethyl;
R4 = in each case one line of Table A.
Table 373 Compounds of the formula I.1, where R3 = methyl;
R5 = 2-fluoroeth-1-yl;
15 R4 = in each case one line of Table A.

Table 374 Compounds of the formula I.2, where R3 = methyl;
20 R5 = 2-fluoroeth-1-yl;
R4 = in each case one line of Table A.

Table 375 Compounds of the formula I.3, where 25 R3 = methyl;
R5 = 2-fluoroeth-1-yl;
R4 = in each case one line of Table A.

Table 376 30 Compounds of the formula I.4, where R3 = methyl;
R5 = 2-fluoroeth-1-yl;
R4 = in each case one line of Table A.

35 Table 377 Compounds of the formula I.l, where R3 = methyl;
R5 = 3-fluoroprop-1-yl;
R4 = in each case one line of Table A.
Table 378 Compounds of the formula I.2, where R3 = methyl;
Rs = 3-fluoroprop-1-yl;
45 R4 = in each case one line of Table A.

Table 379 Compounds of the formula I.3, where R3 = methyl;
R5 = 3-fluoroprop-1-yl;
5 R4 = in each case one line of Table A.

Table 380 Compounds of the formula I.4, where R3 = methyl;
10 R5 = 3-fluoroprop-1-yl;
R4 = in each case one line of Table A.

Table 381 Compounds of the formula I.1, where 15 R3 = methyl;
R5 = 2,2-difluoroeth-1-yl;
R4 = in each case one line of Table A.

Table 382 20 Compounds of the formula I.2, where R3 = methyl;
R5 = 2,2-difluoroeth-1-yl;
R4 = in each case one line of Table A.

25 Table 383 Compounds of the formula I.3, where R3 = methyl;
RS = 2,2-difluoroeth-1-yl;
R4 = in each case one line of Table A.
Table 384 Compounds of the formula I.4 r where R3 = methyl;
R5 = 2,2-difluoroeth-1-yl;
35 R4 = in each case one line of Table A.

Table 385 Compounds of the formula I.l, where R3 = methyl;
40 R5 = 2,2,2-trifluoroeth-1-yl;
R4 = in each case one line of Table A.

Table 386 Compounds of the formula I.2, where 45 R3 = methyl;
R5 = 2,2,2-trifluoroeth-1-yl;

R4 = in each case one line of Table A.

Table 387 Compounds of the formula I.3, where 5 R3 = methyl;
Rs = 2,2,2-trifluoroeth-1-yl;
R4 = in each case one line of Table A.

Table 388 10 Compounds of the formula I.4~ where R3 = methyl;
R5 = 2,2,2-trifluoroeth-1-yl;
R4 = in each case one line of Table A.

lS Table 389 Compounds of the formula I.l, where R3 = methyl;
R5 = 2-bromoeth-1-yl;
R4 = in each case one line of Table A.
Table 390 Compounds of the formula I.2, where R3 = methyl;
R5 = 2-bromoeth-1-yl;
25 R4 = in each case one line of Table A.

Table 391 Compounds of the formula I.3, where R3 = methyl;
30 R5 = 2-bromoeth-1-yl;
R4 = in each case one line of Table A.

Table 392 Compounds of the formula I.4, where 35 R3 = methyl;
R5 = 2-bromoeth-1-yl;
R4 = in each case one line of Table A.

Table 393 40 Compounds of the formula I.1, where R3 = methyl;
R5 = 3-bromoprop-1-yl;
R4 = in each case one line of Table A.

45 Table 394 Compounds of the formula I.2, where R3 = methyl;

R5 = 3-bromoprop-1-yl;
R4 = in each case one line of Table A.

Table 395 5 Compounds of the formula I.3, where R3 = methyl;
R5 = 3-bromoprop-1-yl;
R4 = in each case one line of Table A.

10 Table 396 Compounds of the formula I.4, where R3 = methyl;
R5 = 3-bromoprop-1-yl;
R4 = in each case one line of Table A.
Table 397 Compounds of the formula I.l, where R3 = methyl;
R5 = 4-bromobut-1-yl;
20 R4 = in each case one line of Table A.

Table 398 Compounds of the formula I.2~ where R3 = methyl;
25 R5 = 4-bromobut-1-yl;
R4 = in each case one line of Table A.

Table 399 Compounds of the formula I.3, where 30 R3 = methyl;
R5 = 4-bromobut-1-yl;
R4 = in each case one line of Table A.

Table 400 35 Compounds of the formula I.4, where R3 = methyl;
R5 = 4-bromobut-1-yl;
R4 = in each case one line of Table A.

40 Table 401 Compounds of the formula I.1, where R3 = methyl;
R5 = 2-iodoeth-1-yl;
R4 = in each case one line of Table A.
Table 402 Compounds of the formula I.2, where CA 0223l66l l998-04-07 0050~4~271 R3 = methyl;
R5 = 2-iodoeth-1-yl;
R4 = in each case one line of Table A.

S Table 403 Compounds of the formula I.3, where R3 = methyl;
R5 = 2-iodoeth-1-yl;
R4 = in each case one line of Table A.
Table 404 Compounds of the formula I.4, where R3 = methyl;
Rs = 2-iodoeth-1-yl;
15 R4 = in each case one line of Table A.

Table 405 Compounds of the formula I.l, where R3 = methyl;
20 RS = 2-chloroeth-1-yl;
R4 = in each case one line of Table A.

Table 406 Compounds of the formula I.2, where 25 R3 = methyl;
R5 = 2-chloroeth-1-yl;
R4 = in each case one line of Table A.

Table 407 30 Compounds of the formula I.3, where R3 = methyl;
R5 = 2-chloroeth-1-yl;
R4 = in each case one line of Table A.

35 Table 408 Compounds of the formula I.4, where R3 = methyl;
R5 = 2-chloroeth-1-yl;
R4 = in each case one line of Table A.
Table 409 Compounds of the formula I.l, where R3 = methyl;
R5 = 3-chloroprop-1-yl;
45 R4 = in each case one line of Table A.

~050/46271 Table 410 Compounds of the formula I.2, where R3 = methyl;
R5 = 3-chloroprop-1-yl;
5 R4 = in each case one line of Table A.

Table 411 Compounds of the formula I.3, where R3 = methyl;
10 R5 = 3-chloroprop-1-yl;
R4 = in each case one line of Table A.

Table 412 Compounds of the formula I.4, where 15 R3 = methyl;
R5 = 3-chloroprop-1-yl;
R4 = in each case one line of Table A.

Table 413 20 Compounds of the formula I.1, where R3 = methyl;
R5 = 4-chlorobut-1-yl;
R4 = in each case one line of Table A.

25 Table 414 Compounds of the formula I.2, where R3 = methyl;
R5 = 4-chlorobut-1-yl;
R4 = in each case one line of Table A.
Table 415 Compounds of the formula I.3, where R3 = methyl;
R5 = 4-chlorobut-1-yl;
35 R4 = in each case one line of Table A.

Table 416 Compounds of the formula I.4, where R3 = methyl;
40 R5 = 4-chlorobut-1-yl;
R4 = in each case one line of Table A.

Table 417 Compounds of the formula I.l~ where 45 R3 = methyl;
R5 = cyanomethyl;

UUSO/4~71 R4 = in each case one line of Table A.

Table 418 Compounds of the formula I.2, where 5 R3 = methyl;
R5 = cyanomethyl;
R4 = in each case one line of. Table A.

Table 419 10 Compounds of the formula I.3, where R3 = methyl;
R5 = cyanomethyl;
R4 = in each case one line of Table A.

15 Table 420 Compounds of the formula I.4 t where R3 = methyl;
R5 = cyanomethyl;
R4 = in each case one line of Table A.
Table 421 Compounds of the formula I.ll where R3 = methyl;
R5 = 2-cyanoeth-1-yl;
25 R4 = in each case one line of Table A.

Table 422 Compounds of the formula I.2 r where R3 = methyl;
30 R5 = 2-cyanoeth-1-yl;
R4 = in each case one line of Table A.

Table 423 Compounds of the formula I.3 r where 35 R3 = methyl;
RS = 2-cyanoeth-1-yl;
R4 = in each case one line of Table A.

Table 424 40 Compounds of the formula I.4, where R3 = methyl;
R5 = 2-cyanoeth-1-yl;
R4 = in each case one line of Table A.

45 Table 425 Compounds of the formula I.1, where R3 = methyl;

R5 = 3-cyanoprop-1-yl;
R4 = in each case one line of Table A.

Table 426 5 Compounds of the formula I.2, where R3 = methyl;
R5 = 3-cyanoprop-l-yl;
R4 = in each case one line of Table A.

10 Table 427 Compounds of the formula I.3, where R3 = methyl;
R5 = 3-cyanoprop-1-yl;
R4 = in each case one line of Table A.
Table 428 Compounds of the formula I.4, where R3 = methyl;
R5 = 3-cyanoprop-1-yl;
20 R4 = in each case one line of Table A.

Table 429 Compounds of the formula I.1, where R3 = methyl;
25 R5 = 4-cyanobut-1-yl;
R4 = in each case one line of Table A.

Table 430 Compounds of the formula I.2, where 30 R3 = methyl;
R5 = 4-cyanobut-1-yl;
R4 = in each case one line of Table A.

Table 431 35 Compounds of the formula I.3, where R3 = methyl;
R5 = 4-cyanobut-1-yl;
R4 = in each case one line of Table A.

40 Table 432 Compounds of the formula I.4, where R3 = methyl;
R5 = 4-cyanobut-1-yl;
R4 = in each case one line of Table A.
Table 433 Compounds of the formula I.1, where R3 = methyl;
R5 = 2-ethoxyeth-1-yl;
R4 = in each case one line of Table A.

5 Table 434 Compounds of the formula I.2, where R3 = methyl;
R5 = 2-ethoxyeth-1-yl;
R4 = in each case one line of Table A.
Table 435 Compounds of the formula I.3, where R3 = methyl;
Rs = 2-ethoxyeth-1-yl;
15 R4 = in each case one line of Table A.

Table 436 Compounds of the formula I.4, where R3 = methyl;
20 R5 = 2-ethoxyeth-1-yl;
R4 = in each case one line of Table A.

Table 437 Compounds of the formula I.1, where 25 R3 = methyl;
R5 = 2-isopropoxyeth-1-yl;
R4 = in each case one line of Table A.

Table 438 30 Compounds of the formula I.2, where R3 = methyl;
RS = 2-isopropoxyeth-1-yl;
R4 = in each case one line of Table A.

35 Table 439 Compounds of the formula I.3, where R3 = methyl;
RS = 2-isopropoxyeth-1-yl;
R4 = in each case one line of Table A.
Table 440 Compounds of the formula I.4, where R3 = methyl;
RS = 2-isopropoxyeth-1-yl;
45 R4 = in each case one line of Table A.

0050/ 4t~7 1 Table 441 Compounds of the formula I.l, where R3 = methyl;
R5 = 3-methoxyprop-1-yl;
5 R4 = in each case one line of Table A.

Table 442 Compounds of the formula I.2, where R3 = methyl;
lO R5 = 3-methoxyprop-1-yl;
R4 = in each case one line of Table A.

Table 443 Compounds of the formula I.3, where 15 R3 = methyl;
R5 = 3-methoxyprop-1-yl;
R4 = in each case one line of Table A.

Table 444 20 Compounds of the formula I.4, where R3 = methyl;
R5 = 3-methoxyprop-1-yl;
R4 = in each case one line of Table A.

25 Table 445 Compounds of the formula I.l, where R3 = methyl;
R5 = 3-ethoxyprop-1-yl;
R4 = in each case one line of Table A.
Table 446 Compounds of the formula I.2,. where R3 = methyl;
R5 = 3-ethoxyprop-1-yl;
35 R4 = in each case one line of Table A.

Table 447 Compounds of the formula I.3, where R3 = methyl;
40 Rs = 3-ethoxyprop-1-yl;
R4 = in each case one line of Table A.

Table 448 Compounds of the formula I.4, where 45 R3 = methyl;
RS = 3-ethoxyprop-1-yl;

R4 = in each case one line of Table A.

Table 449 Compounds of the formula I.l, where 5 R3 = methyl;
R5 = 3-isopropoxyprop-1-yl;
R4 = in each case one line of Table A.

Table 450 10 Compounds of the formula I.2, where R3 = methyl;
R5 = 3-isopropoxyprop-1-yl;
R4 = in each case one line of Table A.

15 Table 451 Compounds of the formula I.3, where R3 = methyl;
R5 = 3-isopropoxyprop-1-yl;
R4 = in each case one line of Table A.
Table 452 Compounds of the formula I.4, where R3 = methyl;
R5 = 3-isopropoxyprop-1-yl;
25 R4 = in each case one line of Table A.

Table 453 Compounds of the formula I.l, where R3 = methyl;
30 R5 = 4-methoxybut-1-yl;
R4 = in each case one line of Table A.

Table 454 Compounds of the formula I.2, where 35 R3 = methyl;
R5 = 4-methoxybut-1-yl;
R4 = in each case one line of Table A.

Table 455 40 Compounds of the formula I.3, where R3 = methyl;
R5 = 4-methoxybut-1-yl;
R4 = in each case one line of Table A.

45 Table 456 Compounds of the formula I.4, where R3 = methyl;

R5 = 4-methoxybut-1-yl;
R4 = in each case one line of Table A.

Table 457 5 Compounds of the formula I.1, where R3 = methyl;
R5 = 4-ethoxybut-1-yl;
R4 = in each case one line of Table A.

10 Table 458 Compounds of the formula I.2, where R3 = methyl;
R5 = 4-ethoxybut-1-yl;
R4 = in each case one line of Table A.
Table 459 Compounds of the formula I.3, where R3 = methyl;
R5 = 4-etho~ybu~-1-yl;
20 R4 = in each case one line of Table A.

Table 460 Compounds of the formula I.4, where R3 = methyl;
25 R5 = 4-ethoxybut-1-yl;
R4 = in each case one line of Table A.

Table 461 Compounds of the formula I.1, where 30 R3 = methyl;
R5 = 4-isopLo~okybut-1-yl;
R4 = in each case one line of Table A.

Table 462 35 Compounds of the formula I.2, where R3 = methyl;
R5 = 4-isopropoxybut-1-yl;
R4 = in each case one line of Table A.

40 Table 463 Compounds of the formula I.3, where R3 = methyl;
R5 = 4-isopropoxybut-1-yl;
R4 = in each case one line of Table A.
Table 464 Compounds of the formula I.4, where R3 = methyl;
R5 = 4-isopropoxybut-1-yl;
R4 = in each case one line of Table A.

5 Table 465 Compounds of the formula I.l, where R3 = methyl;
R5 = 3-methylbut-2-en-1-yl;
R4 = in each case one line of Table A.
Table 466 Compounds of the formula I.2, where R3 = methyl;
R5 = 3-methylbut-2-en-1-yl;
15 R4 = in each case one line of Table A.

Table 467 Compounds of the formula I.3, where R3 = methyl;
20 R5 = 3-methylbut-2-en-1-yl;
R4 = in each case one line of Table A.

Table 468 Compounds of the formula I.4, where 25 R3 = methyl;
R5 = 3-methylbut-2-en-1-yl;
R4 = in each case one line of Table A.

Table 469 30 Compounds of the formula I.l, where R3 = methyl;
Rs = 2-methylprop-2-en-1-yl;
R4 = in each case one line of Table A.

35 Table 470 Compounds of the formula I.2l where R3 = methyl;
R5 = 2-methylprop-2-en-1-yl;
R4 = in each case one line of Table A.
Table 471 Compounds of the formula I.3~ where R3 = methyl;
R5 = 2-methylprop-2-en-1-yl;
45 R4 = in each case one line of Table A.

Table 472 Compounds of the formula I.4, where R3 = methyl;
R5 = 2-methylprop-2-en-1-yl;
5 R4 = in each case one line of Table A.

Table 473 Compounds of the formula I.l, where R3 = methyl;
10 R5 = but-3-en-1-yl;
R4 = in each case one line of Table A.

Table 474 Compounds of the formula I.2, where 15 R3 = methyl;
R5 = but-3-en-1-yl;
R4 = in each case one line of Table A.

Table 475 20 Compounds of the formula I.3, where R3 = methyl;
R5 = but-3-en-1-yl;
R4 = in each case one line of Table A.

25 Table 476 Compounds of the formula I.4, where R3 = methyl;
R5 = but-3-en--1-yl;
R4 = in each case one line of Table A.
Table 477 Compounds of the formula I.l, where R3 = methyl;
R5 = 2-chloroprop-2-en-1-yl;
35 R4 = in each case one line of Table A.

Table 478 Compounds of the formula I.2, where R3 = methyl;
40 R5 = 2-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 479 Compounds of the formula I.3, where 45 R3 = methyl;
R5 = 2-chloroprop-2-en-1-yl;

R4 = in each case one line of Table A.

Table 480 Compounds of the formula I.4, where 5 R3 = methyl;
R5 = 2-chloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 481 10 Compounds of the formula I.1, where R3 = methyl;
R5 = 3,3-dichloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

15 Table 482 Compounds of the formula I.2, where R3 = methyl;
R5 = 3,3-dichloroprop-2-en-1-yl;
R4 = in each case one line of Table A.
Table 483 Compounds of the formula I.3, where R3 = methyl;
R5 = 3,3-dichloroprop-2-en-1-yl;
25 R4 = in each case one line of Table A.

Table 484 Compounds of the formula I.4, where R3 = methyl;
30 R5 = 3,3-dichloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 485 Compounds of the formula I.l, where 35 R3 = methyl;
R5 = 2,3,3-trichloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 486 40 Compounds of the formula I.2~ where R3 = methyl;
R5 = 2,3,3-trichloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

45 Table 487 Compounds of the formula I.3, where R3 = methyl;

CA 0223l66l l998-04-07 . 0050/46271 R5 = 2,3,3-trichloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 488 5 Compounds of the formula I.4, where R3 = methyl;
R5 = 2,3,3-trichloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

10 Table 489 Compounds of the formula I.1, where R3 = methyl;
R5 = Z-2,3-dichloroprop-2-en-1-yl;
R4 = in each case one line of Table A.
Table 490 Compounds of the formula I.2, where R3 = methyl;
R5 = Z-2,3-dichloroprop-2-en-1-yl;
20 R4 = in each case one line of Table A.

Table 491 Compounds of the formula I.3, where R3 = methyl;
25 R5 = Z-2,3-dichloroprop-2-en-1-yl;
R4 = in each case one line of Table A.
Table 492 Compounds of the formula I.4 t where 30 R3 = methyl;
R5 = Z-2,3-dichloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 493 35 Compounds of the formula I.l, where R3 = methyl;
R5 = E-2,3-dichloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

40 Table 494 Compounds of the formula I.2, where R3 = methyl;
R5 = E-2,3-dichloroprop-2-en-1-yl;
R4 = in each case one line of Table A.
Table 495 Compounds of the formula I.3, where R3 = methyl;
R5 = E-2,3-dichloroprop-2-en-1-yl;
R4 = in each case one line of Table A.

5 Table 496 Compounds of the formula I.4, where R3 = methyl;
RS = E-2,3-dichloroprop-2-en-1-yl;
R4 = in each case one line of Table A.
Table 497 Compounds of the formula I.l, where R3 = methyl;
R5 = Z-3-bromoprop-2-en-1-yl;
15 R4 = in each case one line of Table A.

Table 498 Compounds of the formula I.2, where R3 = methyl;
20 Rs = Z-3-bromoprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 499 Compounds of the formula I.3, where 25 R3 = methyl;
R5 = Z-3-bromoprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 500 30 Compounds of the formula I.4, where R3 = methyl;
R5 = Z-3-bromoprop-2-en-1-yl;
R4 = in each case one line of Table A.

35 Table 501 Compounds of the formula I.l, where R3 = methyl;
Rs = E-3-bromoprop-2-en-1-yl;
R4 = in each case one line of Table A.
Table 502 Compounds of the formula I.2, where R3 = methyl;
R5 = E-3-bromoprop-2-en-l-yl;
45 R4 = in each case one line of Table A.

Table 503 Compounds of the formula I.3, where R3 = methyl;
R5 = E-3-bromoprop-2-en-1-yl;
5 R4 = in each case one line of Table A.

Table 504 Compounds of the formula I.4, where R3 = methyl;
10 R5 = E-3-bromoprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 505 Compounds of the formula I.l, where 15 R3 = methyl;
R5 = 2-bromoprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 506 20 Compounds of the formula I.2, where R3 = methyl;
R5 = 2-bromoprop-2-en-1-yl;
R4 = in each case one line of Table A.

25 Table 507 Compounds of the formula I.3, where R3 = methyl;
R5 = 2-bromoprop-2-en-1-yl;
R4 = in each case one line of Table A.
Table 508 Compounds of the formula I.4, where R3 = methyl;
R5 = 2-bromoprop-2-en-1-yl;
35 R4 = in each case one line of Table A.

Table 509 Compounds of the formula I.1, where R3 = methyl;
40 R5 = 3,3-dibromoprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 510 Compounds of the formula I.2, where 45 R3 = methyl;
R5 = 3,3-dibromoprop-2-en-1-yl;

R4 = in each case one line of Table A.

Table 511 Compounds of the formula I.3, where S R3 = methyl;
R5 = 3,3-dibromoprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 512 10 Compounds of the formula I.4, where R3 = methyl;
Rs = 3,3-dibromoprop-2-en-1-yl;
R4 = in each case one line of Table A.

15 Table 513 Compounds of the formula I.1, where R3 = methyl;
R5 = 2,3,3-tribromoprop-2-en-1-yl;
R4 = in each case one line of Table A.
Table 514 Compounds of the formula I.2, where R3 = methyl;
R5 = 2,3,3-tribromoprop-2-en-1-yl;
25 R4 = in each case one line of Table A.

Table 515 Compounds of the formula I.3, where R3 = methyl;
30 R5 = 2,3,3-tribromoprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 516 Compounds of the formula I.4, where 35 R3 = methyl;
RS = 2,3,3-tribromoprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 517 40 Compounds of the formula I.1, where R3 = methyl;
Rs = Z-2,3-dibromoprop-2-en-l-yl;
R4 = in each case one line of Table A.

45 Table 518 Compounds of the formula I.2, where R3 = methyl;

R5 = Z-2,3-dibromoprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 519 5 Compounds of the formula I.3, where R3 = methyl;
R5 = Z-2,3-dibromoprop-2-en-1-yl;
R4 = in each case one line of Table A.

10 Table 520 Compounds of the formula I.4, where R3 = methyl;
R5 = Z-2,3-dibromoprop-2-en-l-yl;
R4 = in each case one line of Table A.
Table 521 Compounds of the formula I.l, where R3 = methyl;
Rs = E-2,3-dibromoprop-2-en-1-yl;
20 R4 = in each case one line of Table A.

Table 522 Compounds of the formula I.2, where R3 = methyl;
25 R5 = E-2,3-dibromoprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 523 Compounds of the formula I.3 r where 30 R3 = methyl;
R5 = E-2,3-dibromoprop-2-en-1-yl;
R4 = in each case one line of Table A.

Table 524 35 Compounds of the formula I.4, where R3 = methyl;
R5 = E-2,3-dibromoprop-2-en-1-yl;
R4 = in each case one line of Table A.

40 Table 525 Compounds of the formula I.1, where R3 = methyl;
Rs = E-2-chlorobut-2-en-1-yl;
R4 = in each case one line of Table A.
Table 526 Compounds of the formula I.2, where R3 = methyl;
R5 = E-2-chlorobut-2-en-1-yl;
R4 = in each case one line of Table A.

5 Table 527 Compounds of the formula I.3, where R3 = methyl;
R5 = E-2-chlorobut-2-en-1-yl;
R4 = in each case one line of Table A.
Table 528 Compounds of the formula I.4, where R3 = methyl;
R5 = E-2-chlorobut-2-en-1-yl;
15 R4 = in each case one line of Table A.

Table 529 Compounds of the formula I.l, where R3 = methyl;
20 R5 = Z-2-chlorobut-2-en-1-yl;
R4 = in each case one line of Table A.

Table 530 Compounds of the formula I.2, where 25 R3 = methyl;
Rs = Z-2-chlorobut-2-en-1-yl;
R4 = in each case one line of Table A.

Table 531 30 Compounds of the formula I.3, where R3 = methyl;
Rs = Z-2-chlorobut-2-en-1-yl;
R4 = in each case one line of Table A.

35 Table 532 Compounds of the formula I.4, where R3 = methyl;
R5 = Z-2-chlorobut-2-en-1-yl;
R4 = in each case one line of Table A.
Table 533 Compounds of the formula I.l, where R3 = methyl;
R5 = E-3-chlorobut-2-en-1-yl;
~ 45 R4 = in each case one line of Table A.

Table 534 Compounds of the formula I.2, where R3 = methyl;
R5 = E-3-chlorobut-2-en-1-yl;
5 R4 = in each case one line of Table A.

Table 535 Compounds of the formula I.3, where R3 = methyl;
10 R5 = E-3-chlorobut-2-en-1-yl;
R4 = in each case one line of Table A.

Table 536 Compounds of the formula I.4, where 15 R3 = methyl;
R5 = E-3-chlorobut-2-en-1-yl;
R4 = in each case one line of Table A.

Table 537 20 Compounds of the formula I.l, where R3 = methyl;
R5 = Z-3-chlorobut-2-en-1-yl;
R4 = in each case one line of Table A.

25 Table 538 Compounds of the formula I.2, where R3 = methyl;
R5 = Z-3-chlorobut-2-en-1-yl;
R4 = in each case one line of Table A.
Table 539 Compounds of the formula I.3, where R3 = methyl;
R5 = Z-3-chlorobut-2-en-1-yl;
35 R4 = in each case one line of Table A.

Table 540 Compounds of the formula I.4, where R3 = methyl;
40 R5 = Z-3-chlorobut-2-en-1-yl;
R4 = in each case one line of Table A.

Table 541 Compounds of the formula I.l, where 45 R3 = methyl;
R5 = E-2-bromobut-2-en-1-yl;

R4 = in each case one line of Table A.

Table 542 Compounds of the formula I.2, where 5 R3 = methyl;
R5 = E-2-bromobut-2-en-1-yl;
R4 = in each case one line of Table A.

Table 543 10 Compounds of the formula I.3, where R3 = methyl;
R5 = E-2-bromobut-2-en-1-yl;
R4 = in each case one line of Table A.

15 Table 544 Compounds of the formula I.4, where R3 = methyl;
R5 = E-2-bromobut-2-en-1-yl;
R4 = in each case one line of Table A.
Table 545 Compounds of the formula I.1, where R3 = methyl;
R5 = Z-2-bromobut-2-en-1-yl;
25 R4 = in each case one line of Table A.

Table 546 Compounds of the formula I.2, where R3 = methyl;
30 R5 = Z-2-bromobut-2-en-1-yl;
R4 = in each case one line of Table A.

Table 547 Compounds of the formula I.3, where 35 R3 = methyl;
R5 = Z-2-bromobut-2-en-1-yl;
R4 = in each case one line of Table A.

Table 548 40 Compounds of the formula I.4, where R3 = methyl;
R5 = Z-2-bromobut-2-en-1-yl;
R4 = in each case one line of Table A.

45 Table 549 Compounds of the formula I.1, where R3 = methyl;

RS = E-3-bromobut-2-en-l-yl;
R4 = in each case one line of Table A.

Table 550 5 Compounds of the formula I.2 r where R3 = methyl;
R5 = E-3-bromobut-2-en-1-yl;
R4 = in each case one line of Table A.

10 Table 551 Compounds of the formula I.3, where R3 = methyl;
R5 = E-3-bromobut-2-en-1-yl;
R4 = in each case one line of Table A.
Table 552 Compounds of the formula I.4, where R3 = methyl;
R5 = E-3-bromobut-2-en-1-yl;
20 R4 = in each case one line of Table A.

Table 553 Compounds of the formula I.1, where R3 = methyl;
25 R5 = Z-3-bromobut-2-en-1-yl;
R4 = in each case one line of Table A.

Table 554 Compounds of the formula I.2, where 30 R3 = methyl;
R5 = Z-3-bromobut-2-en-1-yl;
R4 = in each case one line of Table A.

Table 555 35 Compounds of the formula I.3, where R3 = methyl;
R5 = Z-3-bromobut-2-en-1-yl;
R4 = in each case one line of Table A.

40 Table 556 Compounds of the formula I.4 r where R3 = methyl;
R5 = Z-3-bromobut-2-en-l-yl;
R4 = in each case one line of Table A.
Table 557 Compounds of the formula I.1 r where R3 = methyl;
R5 = 3-chloroprop-2-yn-1-yl;
R4 = in each case one line of Table A.

S Table 5S8 Compounds of the formula I.2, where R3 = methyl;
R5 = 3-chloroprop-2-yn-1-yl;
R4 = in each case one line of Table A.
Table 559 Compounds of the formula I.3, where R3 = methyl;
R5 = 3-chloroprop-2-yn-1-yl;
15 R4 = in each case one line of Table A.

Table 560 Compounds of the formula I.4, where R3 = methyl;
20 R5 = 3-chloroprop-2-yn-1-yl;
R4 = in each case one line of Table A.

Table 561 Compounds of the formula I.l, where 25 R3 = methyl;
R5 = 3-bromoprop-2-yn-1-yl;
R4 = in each case one line of Table A.

Table 562 30 Compounds of the formula I.2, where R3 = methyl;
RS = 3-bromoprop-2-yn-1-yl;
R4 = in each case one line of Table A.

35 Table 563 Compounds of the formula I.3, where R3 = methyl;
R5 = 3-bromoprop-2-yn-1-yl;
R4 = in each case one line of Table A.
Table 564 Compounds of the formula I.4, where R3 = methyl;
R5 = 3-bromoprop-2-yn-1-yl;
45 R4 = in each case one line of Table A.

Table 565 Compounds of the formula I.l, where R3 = methyl;
Rs = 3-iodoprop-2-yn-1-yl;
5 R4 = in each case one line of Table A.

Table 566 Compounds of the formula I.2, where R3 = methyl;
10 R5 = 3-iodoprop-2-yn-1-yl;
R4 = in each case one line of Table A.

Table 567 Compounds of the formula I.3, where lS R3 = methyl;
R5 = 3-iodoprop-2-yn-1-yl;
R4 = in each case one line of Table A.

Table 568 20 Compounds of the formula I.4, where R3 = methyl;
R5 = 3-iodoprop-2-yn-1-yl;
R4 = in each case one line of Table A.

25 Table 569 Compounds of the formula I.l, where R3 = methyl;
RS = but-2-yn-1-yl;
R4 = in each case one line of Table A.
Table 570 Compounds of the formula I.2, where R3 = methyl;
R5 = but-2-yn-1-yl;
35 R4 = in each case one line of Table A.

Table 571 Compounds of the formula I.3, where R3 = methyl;
40 R5 = but-2-yn-1-yl;
R4 = in each case one line of Table A.

Table 572 Compounds of the formula I.4, where 45 R3 = methyl;
R5 = but-2-yn-1-yl;

R4 = in each case one line of Table A.

Table 573 Compounds of the formula I.l, where 5 R3 = methyl;
R5 = but-3-yn-1-yl;
R4 = in each case one line of Table A.

Table 574 10 Compounds of the formula I.2 r where R3 = methyl;
R5 = but-3-yn-1-yl;
R4 = in each case one line of Table A.

15 Table 575 Compounds of the formula I.3, where R3 = methyl;
R5 = but-3-yn-1-yl;
R4 = in each case one line of Table A.
Table 576 Compounds of the formula I.4, where R3 = methyl;
R5 = but-3-yn-1-yl;
25 R4 = in each case one line of Table A.

Table 577 Compounds of the formula I.l, where R3 = methyl;
30 R5 = but-3-yn-2-yl;
R4 = in each case one line of Table A.

Table 578 Compounds of the formula I.2, where 35 R3 = methyl;
R5 = but-3-yn-2-yl;
R4 = in each case one line of Table A.

Table 579 40 Compounds of the formula I.3, where R3 = methyl;
R5 = but-3-yn-2-yl;
R4 = in each case one line of Table A.

45 Table 580 Compounds of the formula I.4, where R3 = methyl;

OOSO~ 4627 1 Rs = but-3-yn-2-yl;
R4 = in each case one line of Table A.

Table 581 5 Compounds of the formula I.l, where R3 = methyl;
R5 = pent-3-yn-1-yl;
R4 = in each case one line of Table A.

10 Table 582 Compounds of the formula I.2, where R3 = methyl;
R5 = pent-3-yn-1-yl;
R4 = in each case one line of Table A.
Table 583 Compounds of the formula I.3, where R3 = methyl;
RS = pent-3-yn-1-yl;
20 R4 = in each case one line of Table A.

Table 584 Compounds of the formula I.4, where R3 = methyl;
25 R5 = pent-3-yn-1-yl;
R4 = in each case one line of Table A.

Table 585 Compounds of the formula I.1, where 30 R3 = methyl;
R5 = pent-4-yn-1-yl;
R4 = in each case one line of Table A.

Table 586 35 Compounds of the formula I.2, where R3 = methyl;
R5 = pent-4-yn-1-yl;
R4 = in each case one line of Table A.

40 Table 587 Compounds of the formula I.3, where R3 = methyl;
R5 = pent-4-yn-1-yl;
R4 = in each case one line of Table A.
Table 588 Compounds of the formula I.4, where R3 = methyl;
R5 = pent-4-yn-1-yl;
R4 = in each case one line of Table A.

5 Table 589 Compounds of the formula I.l, where R3 = methyl;
R5 = pent-3-yn-2-yl;
R4 = in each case one line of Table A.
Table S90 Compounds of the formula I.2, where R3 = methyl;
R5 = pent-3-yn-2-yl;
15 R4 = in each case one line of Table A.

Table S91 Compounds of the formula I.3l where R3 = methyl;
20 R5 = pent-3-yn-2-yl;
R4 = in each case one line of Table A.

Table 592 Compounds of the formula I.4, where 25 R3 = methyl;
R5 = pent-3-yn-2-yl;
R4 = in each case one line of Table A.

Table 593 30 Compounds of the formula I.l, where R3 = methyl;
R5 = cyclohexylmethyl;
R4 = in each case one line of Table A.

35 Table 594 Compounds of the formula I.2, where R3 = methyl;
R5 = cyclohexylmethyl;
R4 = in each case one line of Table A.
Table S9S
Compounds of the formula I.3, where R3 = methyl;
R5 = cyclohexylmethyl;
45 R4 = in each case one line of Table A.

0050,/4627 1 Table 596 Compounds of the formula I.4, where R3 = methyl;
Rs = cyclohexylmethyl;
5 R4 = in each case one line of Table A.

0050,/46271 Table A
No. R4 3 C2Hs 4 n-C3H7 10 5 i-C3H7 6 cyclopropyl 7 n-C4Hg 8 s-C4Hg 15 9 i-C4Hg t-C4Hg 11 n-C5H
12 i-C5H
20 13 neo-CsHll 14 cyclopentyl n-C6H13 16 cyclohexyl 17 cyclobutyl 18 CH2CH2Cl 19 (CH2)4Cl 30 22 (CH2)3cN
23 (CH2)4CN
24 (CH2)6cN
cyclohexylmethyl 35 26 2-cyclohexyleth-1-yl 27 cyclopropylmethyl 28 2-cyclopropyleth-1-yl 29 2-methoxyeth-1-yl 40 30 2-ethoxyeth-1-yl 31 2-isopropoxyeth-1-yl 32 3-methoxyprop-1-yl 33 3-ethoxyprop-1-yl 34 3-isopropoxyprop-1-yl 4-methoxybut-1-yl 36 4-isopropoxybut-1-yl 0050~'4627 1 No. R4 37 prop-2-en-1-yl 5 38 but-2-en-1-yl 39 3-methylbut-2-en-1-yl 2-vinyloxyeth-1-yl 41 allyloxyeth-1-yl 42 2-trifluoromethoxyeth-1-yl 10 43 3-trifluoromethoxyprop-1-yl 44 4-difluoromethoxybut-1-yl hydroxycarbonylmethyl 46 methoxycarbonylmethyl 15 47 aminocarbonylmethyl 48 N-methylaminocarbonylmethyl 49 N,N-dimethylaminocArbonylmethyl 2-hydroxycarbonyleth-1-yl 20 51 2-methoxycarbonyleth-1-yl 52 2-aminocarbonyleth-1-yl 53 2-N-methylaminocarbonyleth-1-yl 54 2-dimethylaminocarbonyleth-1-yl 2-aminoeth-1-yl 25 56 2-aminoprop-1-yl 57 4 -Ar' i nobut- 1--yl 58 3-dimethylaminoprop-1-yl 59 4-aminothiocarbonylbut-1-yl 30 60 E-3-chloLo~Lo~-2-en-1-yl 61 Z-3-chloroprop-2-en-1-yl 62 prop-2-yn-1-yl 63 but-2-yn-1-yl 35 64 but-3-yn-1-yl 3-chloroprop-2-yn-1-yl 66 6-aminocarbonylhex-1-yl 67 3-aminothiocarbonylprop-1-yl 68 2-aminothiocarbonyleth-1-yl 69 aminothiocarbonylmethyl 4-(N,N-dimethylamino)but-1-yl 71 2-(methylthio)eth-1-yl 72 2-(methylsulfonyl)eth-1-yl 45 73 4-(methylthio)prop-1-yl 74 4-(methylsulfonyl)prop-1-yl No. R4 benyzl 79 2,3-F2-C6H3-CH2 2,4-F2-C6H3-CH2 81 2,5-F2-C6H3-CH2 82 2,6-F2-C6H3-CH2 83 3,4-F2-C6H3-CH2 84 3,5-F2-C6H3-CH2 2-Cl-C6H4-CH2 86 3-Cl-C6H4-CH2 87 4-Cl-C6H4-CH2 88 2,3-C12-C6H3-CH2 89 2,4-C12-C6H3-CH2 go 2,5-C12-C6H3-CH2 91 2,6-C12-C6H3-CH2 92 3,4-C12-C6H3-CH2 93 3,5-C12-C6H3-CH2 94 2,3,4-C13-C6H2-CH2 2,3,5-C13-C6H2-CH2 96 2,3,6-C13-C6H2-CH2 97 2,4,5-C13-C6H2-CH2 98 2,4,6-C13-C6H2-CH2 99 3,4,5-C13-C6H2-CH2 100 2-Br-C6H4-CH2 101 3-Br-C6H4-CH2 102 4-Br-C6H4-CH2 103 2,3-Br2-C6H3-CH2 104 2,4-Br2-C6H3-CH2 105 2,5-Br2-C6H3-CH2 106 2,6-Br2-C6H3-CH2 107 3,4-Br2-C6H3-CH2 108 3,5-Br2-C6H3-CH2 109 2-F, 3-cl-c6H3-cH2 110 2-F, 4-Cl-C6H3-CH2 111 2-F, 5-Cl-C6H3-CH2 112 2-F, 3-Br-C6H3-CH2 No. R4 113 2-F, 4-Br-c6H3-cH2 114 2-F, 5-Br-c6H3-cH2 115 2-Cl, 3-Br-c6H3-cH2 116 2-Cl, 4-Br-c6H3-cH2 117 2-Cl, 5-Br-c6H3-cH2 118 3-F, 4-cl-c6H3-cH2 10 119 3-F, S-Cl-C6H3-CH2 120 3-F, 6-Cl-C6H3-CH2 121 3-F, 4-Br-c6H3-cH2 122 3-F, 5-Br-c6H3-cH2 15 123 3-F, 6-Br-C6H3-CH2 124 3-Cl, 4-Br-c6H3-cH2 125 3-Cl, 5-Br-c6H3-cH2 126 3-Cl, 6-Br-c6H3-cH2 20 127 4-F, 5-cl-c6H3-cH2 128 4-F, 6-Cl-C6H3-CH2 129 4-F, 5-Br-C6H3-CH2 130 4-F, 6-Br-C6H3-CH2 131 4-Cl, 5-Br-c6H3-cH2 132 5-F, 6-Cl-C6H3-CH2 133 5-F, 6-Br-C6H3-CH2 134 5-Cl, 6-Br-c6H3-cH2 135 3-Br, 4-Cl, 5-Br-c6H2-cH2 141 4-No2-c6H4-cH2 145 2,3-(CH3)2-C6H3-CH2 146 2,4-(CH3)2-C6H3-CH2 147 2,5-(CH3)2-C6H3-CH2 148 2,6-(CH3)2-C6H3-CH2 45 149 3,4-(CH3~2-C6H3-CH2 150 3~5-(cH3)2-c6H3-cH2 0050~4627 1 No. R4 151 2-C2Hs-C6H4-CH2 154 2-i-C3H7-C6H4-CH2 155 3-i-C3H7-C6H4-CH2 156 4-i-C3H7-C6H4-CH2 10 157 2-cyclohexyl-C6H4-CH2 158 3-cyclohexyl-C6H4-CH2 159 4-cyclohexyl-C6H4-CH2 160 2-vinyl-C6H4-CH2 15 161 3-vinyl-C6H4-CH2 162 4-vinyl-C6H4-CH2 163 2-allyl-C6H4-CH2 164 3-allyl-C6H4-CH2 20 165 4-allyl-C6H4-CH2 167 3-C6Hs-C6H4-cH2 169 3-CH3, 5-t-c4Hs-c6H3-cH2 176 2,3-(OCH3)2-C6H3-CH2 177 2,4-(OCH3)2-C6H3-CH2 35 178 2,5-(OCH3)2-C6H3-CH2 179 3,4-(OCH3)2-C6H3-CH2 180 3,5-(OCH3)2-C6H3-CH2 181 3,4,5-(OCH3)3-C6H2-CH2 183 3-OC2Hs-C6H4-CH2 185 2-O-(n-C3H7)-C6H4-CH2 186 3-O-(n-C3H7)-C6H4-CH2 45 187 4-o-(n-c3H7)-c6H4-cH2 188 2-o-(i-c3H7)-c6H4-cH2 No. R4 189 3-o-(i-C3H7)-C6H4-CH2 190 4-O-(i-C3H7)-C6H4-CH2 191 4-O-(n-C4Hg)-C6H4-CH2 192 3-O-(t-C4Hg)-C6H4-CH2 193 4-O-(n-C6H13)-C6H4-CH2 194 2-O-allyl-C6H4-CH2 10 195 3-o-allyl-C6H4-CH2 196 4-o-allyl-C6H4-CH2 200 2-acetyl-C6H4-CH2 201 3-acetyl-C6H4-CH2 202 4-acetyl-C6H4-CH2 20 203 2-methoxycarbonYl-c6H4-cH2 204 3-methoxycarbonyl-C6H4-CH2 205 4-methoxycarbonYl-C6H4-cH2 206 2-aminocarbonYl-c6H4-cH2 207 3-aminocarbonyl-C6H4-CH2 208 4-aminocarbonyl-C6H4-CH2 209 2-dimethylaminoCarbonyl-c6H4-cH2 210 3-dimethylaminoCarbonyl-c6H4-cH2 211 4-dimethylaminocarbonyl-C6H4-CH2 30 212 2-(N-methylaminoCarbonyl)-c6H4-cH2 213 3-(N-methylaminoCarbonyl)-c6H4-cH2 214 4-(N-methylaminoCarbonyl)-c6H4-cH2 218 2-aminothiocarbonyl-C6H4-CH2 219 3-aminothiocarbonyl-C6H4-CH2 220 4-aminothiocarbonyl-C6H4-CH2 221 2-methoxyiminomethyl-C6H4-CH2 222 3-methoxyiminomethyl-C6H4-CH2 223 4-methoxyiminomethyl-C6H4-CH2 224 3,4-methylenedioXy-c6H3-cH2 45 225 3,4-difluoromethylenedioxy-C6H3-CH2 226 2~3-methylenedioxy-c6H3-cH2 0050~4627 1 No. R4 227 2-(l'-methoxyiminoeth-l'-yl)-C6H4-CH2 5 228 3-(l~-methoxyiminoeth-l~-yl)-c6H4-cH2 229 4-(l~-methoxyiminoeth-l~-yl)-c6H4-cH2 242 3-CF3, 4-OCF3-C6H3-CH2 243 l-naphthyl-CH2 244 2-naphthyl-CH2 245 2-phenoxyeth-1-yl 246 2-(2'-chlorophenoxy)eth-1-yl 247 2-(3'-chlorophenoxy)eth-1-yl 248 2-(4'-chlorophenoxy)eth-1-yl 249 2-(3',5'-dichlorophenoxy)eth-1-yl 30 250 2-(2'-cyanophe~oxy)eth-1-yl 251 2-(3'-cyanophenoxy)eth-1-yl 252 2-(4'-cyanophenoxy)eth-1-yl 253 2-(2'-methylphenoxy)eth-1-yl 35 254 2-(3'-methylphenoxy)eth-1-yl 255 2-(4'-methylphenoxy)eth-1-yl 256 2-(3'-t-butylphenoxy)eth-1-yl 257 2-(4'-t-butylphenoxy)eth-1-yl 258 2-(2'-nitrophenoxy)eth-1-yl 259 2-(3'-nitrophenoxy)eth-1-yl 260 2-(4'-nitrophenoxy)eth-1-yl 261 2-(2'-methoxyphenoxy)eth-1-yl 262 2-(3'-methoxyphenoxy)eth-1-yl 263 2-(4'-methoxyphenoxy)eth-1-yl 264 2-(2'-trifluoromethylphenoxy)eth-1-yl No. R4 265 2-(3'-trifluoromethylphenoxy)eth-1-yl 266 2-(4'-trifluoromethylphenoxy)eth-1-yl 267 2-(2'-acetylphenoxy)eth-1-yl 268 2-(3'-acetylphenoxy)eth-1-yl 269 2-(4'-acetylphenoxy)eth-1-yl 270 2-(2'-methoxycarbonyl)eth-1-yl 10 271 2-(3'-methoxycarbonyl)eth-1-yl 272 2-(4'-methoxycarbonyl)eth-1-yl 273 2-(2'-dimethylaminocarbonyl)eth-1-yl 274 2-(3'-dimethylaminocarbonyl)eth-1-yl 15 275 2-(4'-dimethylaminocarbonyl)eth-1-yl 276 2-(2'-aminothiocarbonyl)eth-1-yl 277 2-(3'-aminothiocarbonyl)eth-1-yl 278 2-(4'-aminothiocarbonyl)eth-1-yl 20 279 2-(2'-methylsulfonyl)eth-1-yl 280 2-(3'-methylsulfonyl)eth-1-yl 281 2-(4'-methylsulfonyl)eth-1-yl 282 3-phenoxyprop-1-yl 283 3-(2'-chlorophenoxy)prop-1-yl 284 3-(3'-chlorophenoxy)prop-1-yl 285 3-(4'-chlorophenoxy)prop-1-yl 286 3-(3',5' dichlorophenoxy)prop-l-yl [sic]
287 3-(2'-cyanophenoxy)prop-1-yl 30 288 3-(3'-cyanophenoxy)prop-1-yl 289 3-(4'-cyanophenoxy)prop-1-yl 290 3-(2'-methylphenoxy)prop-1-yl 291 3-(3'-methylphenoxy)prop-1-yl 35 292 3-(4'-methylphenoxy)prop-1-yl 293 3-(2'-methoxyphenoxy)prop-1-yl 294 3-(3'-methoxyphenoxy)prop-1-yl 295 3-(4'-methoxyphenoxy)prop-1-yl 296 3-(2'-trifluoromethylphenoxy)prop-1-yl 297 3-(3'-trifluoromethylphenoxy)prop-1-yl 298 3-(4'-trifluoromethylphenoxy)prop-1-yl 299 4-phenoxybut-1-yl 300 2-phenyleth-1-yl 45 301 2-(2'-chlorophenyl)eth-1-yl 302 2-(3'-chlorophenyl)eth-1-yl 0050/'4627 1 No. R4 303 2-(4'-chlorophenyl)eth-1-yl 304 2-(3',5'-dichlorophenyl)eth-1-yl 305 2-(2'-cyanophenyl)eth-1-yl 306 2-(3'-cyanophenyl)eth-1-yl 307 2-(4'-cyanophenyl)eth-1-yl 308 2-(2'-methylphenyl)eth-l-yl 10 309 2-(3'-methylphenyl)eth-1-yl 310 2-(4'-methylphenyl)eth-1-yl 311 2-(2'-methoxyphenyl)eth-1-yl 312 2-(3'-methoxyphenyl)eth-1-yl 15 313 2-(4'-methoxyphenyl)eth-1-yl 314 2-(2'-trifluoromethylphenyl)eth-1-yl 315 2-(3'-trifluoromethylphenyl)eth-1-yl 316 2-(4'-trifluoromethylphenyl)eth-1-yl 20 317 3-phenylprop-1-yl 318 3-(2'-chlorophenyl)prop-1-yl 319 3-(3'-chlorophenyl)prop-1-yl 320 3-(4'-chlorophenyl)prop-l-yl 321 3-(2'-cyanophenyl)prop-1-yl 322 3-(3'-cyanophenyl)prop-1-yl 323 3-(4'-cyanophenyl)prop-l-yl 324 3-(2'-trifluoromethylphenyl)prop-1-yl 325 4-phenylbut-1-yl 30 326 4-(4'-chlorophenyl)but-1-yl 327 6-(4'-chlorophenyl)hex-1-yl 328 2-pyridylmethyl 329 3-pyridylmethyl 35 330 4-pyridylmethyl 331 4-chloropyridin-2-ylmethyl 332 5-chloropyridin-2-ylmethyl 333 6-chloropyridin-2-ylmethyl 40 334 5-chloropyridin-3-ylmethyl 335 6-chloropyridin-3-ylmethyl 336 2-chloropyridin-4-ylmethyl 337 2-pyrimidinylmethyl 338 4-chloropyrimidin-2-ylmethyl 339 5-chloropyrimidin-2-ylmethyl 340 2-chloropyrimidin-4-ylmethyl No. R4 341 6-chloropyrimidin-4-ylmethyl 342 2-chloropyrimidin-5-ylmethyl 343 4-pyridazinylmethyl 344 2-pyrazinylmethyl 345 5-chloropyrazin-2-ylmethyl 346 6-chloropyrazin-2-ylmethyl 10 347 3-pyridazinylmethyl 348 6-chloropyridazin-3-ylmethyl 349 1,3,5-triazinylmethyl 350 2-furylmethyl 15 351 3-furylmethyl 352 4-bromofur-2-ylmethyl 353 5-chlorofur-2-ylmethyl 354 2-thienylmethyl 20 355 3-thienylmethyl 356 5-methylthien-3-ylmethyl 357 5-chlorothien-2-ylmethyl 358 2-chlorothien-4-ylmethyl 359 2-pyrrolylmethyl 360 3-pyrrolylmethyl 361 2-oxazolylmethyl 362 4-methyloxazol-2-ylmethyl 363 5-methyloxazol-2-ylmethyl 30 364 4-chlorooxazol-2-ylmethyl 365 5-chlorooxazol-2-ylmethyl 366 4-oxazolylmethyl 367 2-methyloxazol-4-ylmethyl 35 368 5-methyloxazol-4-ylmethyl 369 2-chlorooxazol-4-ylmethyl 370 5-chlorooxazol-4-ylmethyl 371 5-oxazolylmethyl 40 372 2-methyloxazol-5-ylmethyl 373 4-methyloxazol-5-ylmethyl 374 2-chlorooxazol-5-ylmethyl 375 4-chlorooxazol-5-ylmethyl 376 2-thiazolylmethyl 45 377 4-methylthiazol-2-ylmethyl 378 5-methylthiazol-2-ylmethyl CA 0223l66l l998-04-07 No. R4 379 4-chlorothiazol-2-ylmethyl 5 380 5-chlorothiazol-2-ylmethyl 381 4-thiazolylmethyl 382 2-methylthiazol-4-ylmethyl 383 5-methylthiazol-4-ylmethyl 384 2-chlorothiazol-4-ylmethyl lO 385 5-chlorothiazol-4-ylmethyl 386 5-thiazolylmethyl 387 2-methylthiazol-5-ylmethyl 388 4-methylthiazol-5-ylmethyl 15 389 2-chlorothiazol-5-ylmethyl 390 4-chlorothiazol-5-ylmethyl 391 3-isoxazolylmethyl 392 4-methylisoxazol-3-ylmethyl 20 393 5-methylisoxazol-3-ylmethyl 394 4-chloroisoxazol-3-ylmethyl 395 5-chloroisoxazol-3-ylmethyl 396 4-isoxazolylmethyl 397 3-methylisoxazol-4-ylmethyl 398 5-methylisoxazol-4-ylmethyl 399 3-chloroisoxazol-4-ylmethyl 400 5-chloroisoxazol-4-ylmethyl 401 5-isoxazolylmethyl 30 402 3-methylisoxazol-5-ylmethyl 403 4-methylisoxazol-5-ylmethyl 404 3-chloroisoxazol-5-ylmethyl 405 4-chloroisoxazol-5-ylmethyl 35 406 3-isothiazolylmethyl 407 4-methylisothiazol-3-ylmethyl 408 5-methylisothiazol-3-ylmethyl 409 4-chloroisothiazol-3-ylmethyl 410 5-chloroisothiazol-3-ylmethyl 411 4-isothiazolylmethyl 412 3-methylisothiazol-4-ylmethyl 413 5-methylisothiazol-4-ylmethyl 414 3-chloroisothiazol-4-ylmethyl 45 415 5-chloroisothiazol-4-ylmethyl 416 5-isothiazolylmethyl 0050~ 4627 1 No. R4 417 3-methylisothiazol-5-ylmethyl 5 418 4-methylisothiazol-5-ylmethyl 419 3-chloroisothiazol-5-ylmethyl 420 4-chloroisothiazol-5-ylmethyl 421 4-imidazolylmethyl 422 1-phenylpyrazol-3-ylmethyl 10 423 1-methylimidazol-4-ylmethyl 424 1-phenyl-1,2,4-triazol-3-ylmethyl 425 1,2,4-oxadiazol-3-ylmethyl 426 5-chloro-1,2,4-oxadiazol-3-ylmethyl 15 427 5-methyl-1,2,4 -OYA~ i A 701- 3-ylmethyl 428 5-trifluoromethyl-1,2,4-oxadiazol-3-ylmethyl 429 1,3,4-oYadiazol-2-ylmethyl 430 5-chloro-1,3,4-oxadiazol-2-ylmethyl 20 431 5-methyl-1,3,4_oYA~;Azol-2-ylmethyl 432 5-methoxy-1,3,4_oYA~iAzol-2-ylmethyl 433 1,2,4-thiadiazol-3-ylmethyl 434 5-chloro-1,2,4-th;a~iAzol-3-ylmethyl 435 5-methyl-1,2,4-thi A~i Azol-3-ylmethyl 436 1,3,4-thi A~ i A zol-2-ylmethyl 437 5-chloro-1,3,4-t h i ~Ad i A zol-2-ylmethyl 438 5-methyl-1,3,4-thi A~i Azol-2-ylmethyl 439 5-cyano-1,3,4-~hi A~ i A zol-2-ylmethyl 30 440 2-(2'-pyridinyloxy)eth-1-yl 441 2-(3'-pyridinyloxy)eth-1-yl 442 2-(4'-pyridinyloxy)eth-1-yl 443 2-(2'-pyrimidinyloxy)eth-1-yl 35 444 2-(4'-pyrimidinyloxy)eth-1-yl 445 2-(5'-pyrimidinyloxy)eth-1-yl 446 2-(2'-pyrazinyloxy)eth-1-yl 447 2-(2'-pyridazinyloxy)eth-1-yl 448 2-(3'-pyridazinyloxy)eth-1-yl 449 2-(l~3~5~-triazinyloxy)eth-l-yl 450 2-(5'-methylisoxazol-3'-yloxy)eth-1-yl 451 2-(5'-chloroisoxazol-3~-yloxy)eth-1-yl 452 2-(2'-methoxythiazol-4~-yloxy)eth-1-yl 45 453 2-(4~-chlorooxazol-2~-yloxy)eth-l-yl 454 2-(1'-phenyl-l'H-1',2',4'-triazol-3'-yloxy)eth-1-yl No. R4 455 2-(1'-phenylpyrazol-3'-yloxy)eth-1-yl 460 2,3-F2-C6H3 10 461 2,4-F2-C6H3 462 2,5-F2-C6H3 463 2,6-F2-C6H3 464 3,4-F2-C6H3 15 465 3,5-F2-C6H3 466 2-Cl-C6H4 467 3-Cl-C6H4 468 4-Cl-C6H4 20 469 2,3-C1 ff 6H3 470 2,4-C12-C6H3 471 2,5-C12-C6H3 472 2,6-C12-C6H3 473 3,4-C12-C6H3 474 3,5-C12-C6H3 475 2,3,4-C13-C6H2 476 2,3,5-C13-C6H2 477 2,3,6-C13-C6H2 30 478 2,4,5-C13-C6H2 479 2,4,6-C1 ff 6H2 480 3,4,5-C13-c6H2 481 2-Br-C6H4 35 482 3-Br-C6H4 483 4-Br-C6H4 484 2,3-Br2-C6H3 485 2,4-Br2-C6H3 486 2,5-Br2-C6H3 487 2,6-Br2-C6H3 488 3,4-Br2-C6H3 489 3,5-Br2-C6H3 490 2-F, 3-Cl-C6H3 45 491 2-F, 4-Cl-C6H3 492 2-F, 5-Cl-C6H3 No. R4 493 2 -F, 3 -Br-c6H3 5 494 2 -F, 4 -Br-c6H3 495 2 - F, 5-Br - C6H3 496 2-Cl, 3-Br-C6H3 497 2-Cl, 4-Br-C6H3 498 2 -Cl, 5-Br-C6H3 10 499 3-F, 4-Cl-C6H3 S00 3-F, 5-Cl-C6H3 501 3-F, 6-Cl - C6H3 502 3-F, 4-Br-C6H3 15 503 3-F, 5-Br-C6H3 504 3-F, 6-Br-C6H3 505 3-Cl, 4-Br-C6H3 506 3-Cl, 5-Br-C6H3 20 507 3-Cl, 6-Br-C6H3 508 4-F, 5-cl-c6H3 509 4-F, 6-Cl-C6H3 S 10 4 -F, 5-Br-C6H3 S l l 4-F, 6-Br-C6H3 512 4-Cl, 5-Br-C6H3 513 5-F, 6-Cl-C6H3 514 5-F, 6-Br-C6H3 515 5-Cl, 6-Br-C6H3 30 516 3-Br, 4-Cl, 5-Br-C6H2 526 2,3 - (CH3)2 - C6H3 527 2,4-(CH3)2-C6H3 528 2,5- ( CH3) 2-C6H3 529 2,6 - ( CH3) 2 - C6H3 530 3,4-(CH3)2 - C6H3 0050~ 4627 1 No. R4 531 3,5-(CH3)2--C6H3 532 2-C2Hs-C6H4 533 3 -C2Hs-C6H4 534 4-C2Hs-C6H4 535 2-i-C3H7-C6H4 536 3-i-C3H7-C6H4 537 4- i-C3H7-C6H4 538 3-tert-C4Hg-C6H4 539 4-tert-C4Hg-C6H4 540 2 -vinyl -C 6 H4 541 3-vinyl-C6H4 542 4 -vinyl -C6 H4 543 2 -a 1 lyl -C6 H4 544 3 -allyl-C6H4 545 4-allyl-C6H4 546 2 -C6Hs-C6H4 548 4-C6Hs-C6H4 549 3-CH3, 5-tert-C4Hg-C6H3 552 4-oH-c6H4 556 2,3- (OCH3) 2-C6H3 557 2,4- (OCH3) 2-C6H3 558 2,5-(OCH3)2-C6H3 559 3,4-(OCH3)2-C6H3 560 3~5--(ocH3)2--C6H3 561 3,4,5--(OCH3)3-C6H2 562 2--Oc2Hs -C6H4 563 3-OC2Hs-C6H4 564 4-OC2Hs-C6H4 565 2 -O- ( n-C3H7) -C6H4 566 3-0- ( n-C3H7) -C6H4 567 4-O-(n-C3H7)-C6H4 568 2-0- ( i-C3H7) -C6H4 0050~4627 1 No. R4 569 ~ 3-O-(i-C3H7)-C6H4 570 4-o-(i-C3H7)-C6H4 571 4-O-(n-C4Hg)-C6H4 572 3-O-(t-C4Hs)-C6H4 573 4_o-(t-C4H9)-c6H4 574 2-O-allyl-C6H4 10 575 3-O-allyl-C6H4 576 4-O-allyl-C6H4 580 2-acetyl-C6H4 581 3-acetyl-C6H4 582 4-acetyl-C6H4 20 583 2-methoxycarbonyl-C6H4 584 3-methoxycarbonyl-C6H4 585 4-methoxycarbonyl-C6H4 586 2-aminocarbonyl-C6H4 587 3-aminocarbonyl-C6H4 588 4-aminocarbonyl-C6H4 589 2-dimethylaminocarbonyl-C6H4 590 3-dimethylaminOcarbonyl-c6H4 591 4-dimethylaminOcarbonyl-c6H4 30 592 2-(N-methylaminocarbonyl)-C6H4 593 3-(N-methylaminocarbonyl)-c6H4 594 4-(N-methylaminocarbonyl)-c6H4 598 2-aminothiocarbonyl-C6H4 599 3-aminothiocarbonyl-C6H4 600 4-aminothiocarbonyl-C6H4 601 2-methoxyiminomethyl-C6H4 602 3-methoxyiminomethyl-C6H4 603 4-methoxyi i n- -thyl-C6H4 604 3,4-methylenedioxy-C6H3 45 605 3,4-difluoromethylenedioxy-C6H3 606 2,3-methylenedioxy-C6H3 CA 0223l66l l998-04-07 No. R4 607 2-(1'-methoxyiminoeth-1'-yl)-C6H4 608 3-(1'-methoxyiminoeth-1'-yl)-C6H4 609 4-(1'-methoxyiminoeth-1'-yl)-C6H4 622 3-CF3, 4-OCF3-C6H3 626 2-N(CH3)2-C6H4 627 3-N(CH3)2-C6H4 628 4-N(CH3)2-C6H4 629 2-ethoxycarbonyl-C6H4 30 630 3-ethoxycarbonyl-C6H4 631 4-ethoxycarbonyl-C6H4 35 634 4-cH2cH2F-c6H4 644 2-(l'-oxo-n-prop-1-yl)-C6H4 No. R4 645 3-(l'-oxo-n-prop-l-yl)-C6H4 5 646 4-(l'-oxo-n-prop-l-yl)-C6H4 647 2-(l~-oxoisoprop-l-yl)-C6H4 648 3-(l'-oxoisoprop-l-yl)-C6H4 649 4-(l'-oxoisoprop-1-yl)-C6H4 650 3-cyclopropyl-C6H4 10 651 4-cyclopropyl-C6H4 652 4-cyclohexyl-C6H4 653 1-naphthyl 654 2-naphthyl 15 655 2-pyridyl 656 3-pyridyl 657 4-pyridyl 658 S-CH3-pyridin-2-yl 20 659 5-Cl-pyridin-2-yl 660 6-C1-pyridin-2-yl 661 3,5-Cl2-pyridin-2-yl 662 6-OCH3-pyridin-2-yl 663 6-CH3-pyridin-2-yl 664 6-Cl-pyridin-3-yl 665 6-CH3-pyridin-3-yl 666 6-OCH3-pyridin-3-yl 667 2-pyrimidinyl 30 668 4-OCH3-pyrimidin-2-yl 669 4-OCzHs-pyrimidin-2-yl 670 4-Cl-pyrimidin-2-yl 671 4-CH3-pyrimidin-2-yl 35 672 5-CH3-pyrimidin-2-yl 673 5-Cl-pyrimidin-2-yl 674 5-OCH3-pyrimidin-2-yl 675 5-OC2Hs-pyrimidin-2-yl 40 676 4-pyrimidinyl 677 2-Cl-pyrimidin-4-yl 678 2-OCH3-pyrimidin-4-yl 679 2-CH3-pyrimidin-4-yl 680 6-Cl-pyrimidin-4-yl 45 681 6-CH3-pyrimidin-4-yl 682 6-OCH3-pyrimidin-4-yl No. R4 683 5-pyrimidinyl 684 2-CH3-pyrimidin-5-yl 685 2-Cl-pyrimidin-5-yl 686 2-OCH3-pyrimidin-5-yl 687 2-OC2Hs-pyrimidin-5-yl 688 2-furyl 10 689 4-C2Hs-fur-2-yl 690 4-CH3-fur-2-yl 691 4-Cl-fur-2-yl 692 4-CN-fur-2-yl 15 693 5-CH3-fur-2-yl 694 5-Cl-fur-2-yl 695 5-CN-fur-2-yl 696 3-furyl 20 697 5-CH3-fur-3-yl 698 5-Cl-fur-3-yl 699 5-CN-fur-3-yl 700 2-thienyl 701 4-CH3-thien-2-yl 702 4-Cl-thien-2-yl 703 4-CN-thien-2-yl 704 5-CH3-thien-2-yl 705 5-Cl-thien-2-yl 30 706 5-CN-thien-2-yl 707 3-thienyl 708 5-CH3-thien-3-yl 709 5-Cl-thien-3-yl 35 710 5-CN-thien-3-yl 711 4-CH3-thien-3-yl 712 5-F-thien-3-yl 713 2-oxazolyl 714 4-CH3-oxazol-2-yl 715 4-Cl-oxazol-2-yl 716 4-CN-oxazol-2-yl 717 5-CH3-oxazol-2-yl 718 5-Cl-oxazol-2-yl 45 719 5-CN-oxazol-2-yl 720 4-oxazolyl No. R4 721 2-CH3-oxazol-4-yl 722 2-Cl-oxazol-4-yl 723 2-CN-oxazol-4-yl 724 5-oxazolyl 725 2-CH3-oxazol-5-yl 726 2-Cl-oxazol-5-yl 10 727 2-CN-oxazol-5-yl 728 3-isoxazolyl 729 5-CH3-isoxazol-3-yl 730 5-Cl-isoxazol-3-yl 15 731 5-CN-isoxazol-3-yl 732 5-isoxxazolyl [sic]
733 3-CH3-isoxazol-5-yl 734 3-Cl-isoxazol-5-yl 20 735 3-CN-isoxazol-5-yl 736 2-thiazolyl 737 4-CH3-thiazol-2-yl 738 4-Cl-thiazol-2-yl 739 4-CN-thiazol-2-yl 740 5-CH3-thiazol-2-yl 741 5-Cl-thiazol-2-yl 742 5-CN-thiazol-2-yl 743 4-thiazolyl 30 744 2-CH3-thiazol-4-yl 745 2-Cl-thiazol-4-yl 746 2-CN-thiazol-4-yl 747 2-SCH3-thiazol-4-yl 35 748 5-thiazolyl 749 2-CH3-thiazol-5-yl 750 2-Cl-thiazol-5-yl 751 2-CN-thiazol-5-yl 752 3-isothiazolyl 753 5-CH3-isothiazol-3-yl 754 5-Cl-isothiazol-3-yl 755 5-CN-isothiazol-3-yl 756 5-isothiazolyl 45 757 3-CH3-isothiazol-5-yl 758 3-Cl-isothiazol-5-yl No. R4 759 3-CN-isothiazol-5-yl 760 2-imidazolyl 761 4-CH3-imidazol-2-yl 762 4-Cl-imidazol-2-yl 763 4-CN-imidazol-2-yl 764 l-CH3-imidazol-2-yl 10 765 l-CH3, 4-Cl-imidazol-2-yl 766 1,4-(CH3)2-imidazol-2-yl 767 l-CH3, 5-Cl-imidazol-2-yl 768 1,5-(CH3)2-imidazol-2-yl 15 769 4-imidazolyl 770 2-CH3-imidazol-4-yl 771 2-Cl-imidazol-4-yl 772 1-CH3-imidazol-4-yl 20 773 1,2-(CH3)2-imidazol-4-yl 774 1-CH3, 2-Cl-imidazol-4-yl 775 1-CH3-imidazol-5-yl 776 1-CH3, 3-Cl-imidazol-5-yl 777 1,2-~CH3)2-imidazol-S-yl 778 3-pyrazolyl 779 5-CH3-pyrazol-3-yl 780 5-Cl-pyrazol-3-yl 781 5-CN-pyrazol-3-yl 30 782 1-CH3-pyrazol-3-yl 783 1-CH3, 4-Cl-pyrazol-3-yl 784 1-CH3, 5-Cl-pyrazol-3-yl 785 1,5-(CH3)2-pyrazol-3-yl 35 786 1-CH3-pyrazol-5-yl 787 l-CH3, 3-Cl-pyrazol-5-yl 788 1,3-(CH3)2-pyrazol-5-yl 789 4-pyrazolyl 790 3-Cl-pyrazol-4-yl 791 3-CH3-pyrazol-4-yl 792 l-CH3-pyrazol-4-yl 793 1-CH3, 3-Cl-pyrazol-4-yl 794 1,3-(CH3)2-pyrazol-4-yl 45 795 1,3,4-oxadiazol-5-yl 796 2-CH3-1,3,4-oxadiazol-5-yl CA 0223l66l l998-04-07 No. R4 797 2-Cl-1,3,4-oxadiazol-5-yl 5 798 2-CF3-1,3,4-oxadiazol-5-yl 799 2-i-C3H7-1,3,4-oxadiazol-5-yl 800 2-OCH3-1,3,4 - O~A~ i A zol-5-yl 801 1,2,4-oxadiazol-3-yl 802 5-CH3-1,2,4-oxadiazol-3-yl 803 5-i-C3H7-1,2,4-o~A~;Azol-3-yl 804 S-Cl-1,2,4-oxadiazol-3-yl 805 S-CF3-1,2,4-oxadiazol-3-yl 806 1,2,4-triazol-3-yl 15 807 1-CH3-1,2,4-triazol-3-yl 808 3-fluoropyridin-2-yl 809 3-chloropyridin-2-yl 810 3-bromopyridin-2-yl 20 811 3-methylpyridin-2-yl 812 3-trifluoromethylpyridin-2-yl 813 3-methoxypyridin-2-yl 814 4-fluoropyridin-2-yl 815 4-chloropyridin-2-yl 816 4-bromopyridin-2-yl 817 4-methylpyridin-2-yl 818 4-trifluoromethylpyridin-2-yl 819 4-methoxypyridin-2-yl 30 820 S-fluoropyridin-2-yl 821 S-bromopyridin-2-yl 822 6-trifluoromethylpyridin-2-yl 823 2-fluoropyridin-3-yl 35 824 2-chloropyridin-3-yl 825 2-bromopyridin-3-yl 826 2-methylpyridin-3-yl 827 2-trifluoromethylpyridin-3-yl 40 828 3-methoxypyridin-3-yl 829 4-fluoropyridin-3-yl 830 4-chloropyridin-3-yl 831 4-bromopyridin-3-yl 832 4-methylpyridin-3-yl 45 833 4-trifluoromethylpyridin-3-yl 834 4-methoxypyridin-3-yl CA 0223l66l l998-04-07 No. R4 835 5-fluoropyridin-3-yl 836 5-chloropyridin-3-yl 837 5-bromopyridin-3-yl 838 5-methylpyridin-3-yl 839 5-trifluoromethylpyridin-3-yl 840 5-methoxypyridin-3-yl 10 841 6-fluoropyridin-3-yl 842 6-bromopyridin-3-yl 843 6-trifluoromethylpyridin-3-yl 844 2-fluoropyridin-4-yl 15 845 2-chloropyridin-4-yl 846 2-bromopyridin-4-yl 847 2-methylpyridin-4-yl 848 2-trifluoromethylpyridin-4-yl 20 849 2-methoxypyridin-4-yl 850 3-fluoropyridin-4-yl 851 3-chloropyridin-4-yl 852 3-bromopyridin-4-yl 853 3-methylpyridin-4-yl 854 3-trifluoromethylpyridin-4-yl 855 3-methoxypyridin-4-yl 856 4-fluoropyrimidin-2-yl 857 4-bromopyrimidin-2-yl 30 858 4-trifluoromethylpyrimidin-2-yl 859 5-fluoropyrimidin-2-yl 860 5-bromopyrimidin-2-yl 861 5-trifluoromethylpyrimidin-2-yl 35 862 2-fluoropyrimidin-4-yl 863 2-bromopyrimidin-4-yl 864 2-trifluoromethylpyrimidin-4-yl 865 2-trifluoromethoxypyrimidin-4-yl 866 5-fluoropyrimidin-4-yl 867 5-chloropyrimidin-4-yl 868 5-bromopyrimidin-4-yl 869 5-methoxypyrimidin-4-yl 870 5-trifluoromethylpyrimidin-4-yl 871 5-methoxypyrimidin-4-yl 872 6-fluoropyrimidin-4-yl CA 0223l66l l998-04-07 No. R4 8736-bromopyrimidin-4-yl 874 6-trifluoromethylpyrimidin-4-yl 875 2-fluoropyrimidin-5-yl 876 2-br.- ~p~.imidin-5-yl 877 2-trifluoromethylpyrimidin-5-yl 878 4-fluoropyrimidin-5-yl 10 879 4-chloropyrimidin-5-yl 880 4-bromopyrimidin-5-yl 881 4-methylpyrimidin-5-yl 882 4-trifluoromethylpyrimidin-5-yl 883 3-fluoro-5-trifluoromethylpyridin-2-yl 884 3,6-dichloro-5-trifluoromethylpyridin-2-yl 885 5,6-dichloro-3-trifluoromethylpyridin-2-yl 886 5-chloro-3-trifluoromethylpyridin-2-yl 20 887 3-chloro-5-trifluoromethylpyridin-2-yl 888 6-chloro-4-cyanopyridin-2-yl 889 3-cyano-5-nitropyridin-2-yl 890 2-chloro-6-fluoropyridin-4-yl 891 6-chloro-4-fluoropyridin-2-yl 892 4,6-difluoropyridin-2-yl 893 3,5-dichloro-6-fluoropyridin-2-yl 894 6-methoxy-3-nitropyridin-2-yl 895 4-cyano-6-fluoropyridin-2-yl 30 896 6-chloro-5-cyanopyridin-2-yl 897 6-chloro-3-cyanopyridin-2-yl 898 4-cyano-3,5,6-trifluoropyridin-2-yl 899 6-chloro-5-nitropyridin-2-yl 35 900 6-chloro-3-nitropyridin-2-yl 901 5-cyano-6-fluoropyridin-2-yl 902 3-cyano-6-fluoropyridin-2-yl 903 4,6-dicyanopyridin-2-yl 904 5-trichloromethylpyridin-2-yl 905 5-cyanopyridin-2-yl 906 5-bromo-4-trifluoromethylpyridin-2-yl 907 3-nitro-5-trifluoromethylpyridin-2-yl 908 5-aminopyridin-2-yl 45 909 2,3,5,6-tetrafluoropyridin-4-yl 910 S-nitropyridin-2-yl No. R4 911 4-methyl-5-nitroypridin-2-yl [sic]
5 912 5-difluoromethylpyridin-2-yl 913 5-fluoromethylpyridin-2-yl 914 4,6-difluoropyrimidin-2-yl 915 2,6-difluoropyrimidin-4-yl 916 2-chloro-6-trichloromethylpyrimidin-4-yl 10 917 2,6-dichloropyrimidin-4-yl 918 5-methoxycarbonylpyridin-2-yl 919 5-chloro-6-fluoropyridin-2-yl 920 5-chloro-6-hydroxypyridin-2-yl 921 5-chloro-6-methoxypyridin-2-yl 922 5-chloro-6-cyanopyridin-2-yl 923 5,6-dichloropyridin-2-yl 924 6-bromo-5-chloropyridin-2-yl 20 925 5-bromo-6-fluoropyridin-2-yl 926 5-bromo-6-chloropyridin-2-yl 927 5-bromo-6-cyanopyridin-2-yl 928 S-bromo-6-hydroxypyridin-2-yl 929 5-bromo-6-methoxypyridin-2-yl 930 5,6-dibL~ ~p~idin-2-yl 931 4-cyanopyridin-2-yl 932 6-cyanopyridin-2-yl 933 4-chloro-6-methylpyrimidin-2-yl 30 934 2-chloro-6-fluoropyridin-4-yl 935 5-bromo-4-trifluoromethylpyridin-2-yl 936 4,5-dichloropyridin-2-yl 937 4,5-dibromopyridin-2-yl 35 938 5,6-dichloropyridin-2-yl 939 4,6-dichloropyridin-2-yl 940 4,6-dibromopyridin-2-yl 941 5,6-dibromopyridin-2-yl 40 942 4-bromo-5-chloropyridin-2-yl 943 6-bromo-5-chloropyridin-2-yl 944 5-bromo-4-chloropyridin-2-yl 945 5-bromo-4-chloropyridin-2-yl 946 6-bromo-4-chloropyridin-2-yl 45 947 4-bromo-6-chloropyridin-2-yl 948 6-chloro-4-methoxypyridin-2-yl CA 0223l66l l998-04-07 No. R4 949 6-bromo-4-methoxypyridin-2-yl 950 6-chloroquinazolin-2-yl 9Sl quinazolin-2-yl 952 4-cyanopyridin-2-yl 953 6-cyanopyridin-2-yl 954 5-hydroxymethylpyridin-2-yl 10 955 6-chloro-4-trifluoromethylpyridin-2-yl 956 6-chloro-4-trifluoromethylpyridin-2-yl 957 6-chloro-4-methylpyridin-2-yl 958 2,5-dichloro-6-cyanopyridin-2-yl 15 959 2,5-dichloro-6-carboxypyridin-2-yl 960 2,5-dichloro-6-methoxycarbonylpyridin-2-yl 961 6-trifluoromethylpyridin-2-yl 962 6-methoxycarbonylpyridin-2-yl 20 963 6-carboxypyridin-2-yl 964 4-phenoxypyridin-2-yl 965 5-phenoxypyridin-2-yl 966 6-phenoxypyridin-2-yl 967 4-phenoxypyrimidin-4-yl 968 4-~4-methylphenoxy)pyrimidin-4-yl 969 4-phenoxypyrimidin-2-yl 970 4-(2-fluorophenoxy)pyrimidin-2-yl 971 4-pheno~y~-yLimidin-6-yl 30 972 4-(4-chlorophenoxy)pyrimidin-6-yl 973 4-(2-pyridyloxy)pyrimidin-6-yl 974 4-(6-chloro-2-pyridyloxy)pyrimidin-6-yl 975 4-(3-pyridyloxy)pyrimidin-6-yl 976 4-(2-methyl-3-pyridyloxy)pyrimidin-6-yl 977 4-(4-pyridyloxy)pyrimidin-6-yl 978 5-bromo-2-thienyl 979 5-nitro-2-thienyl 980 2-chloro-3-thienyl 981 2-bromo-3-thienyl 982 l-methyl-3-pyrrolyl 983 1-methyl-2-pyrrolyl 984 1-benzofuran-2-yl 45 985 l-benzofuran-3-yl 986 1-benzothiophen-2-yl 0050~46271 No. R4 987 1-benzothiophen-3-yl 5 988 3-pyrrolyl 989 2-pyrrolyl 990 3-indolyl 991 2-indolyl 992 1-methyl-3-indolyl lO 993 1-methyl-2-indolyl 994 isoxazol-4-yl 99S isothiazol-4-yl 996 1,2-benzisoxazol-3-yl 15 997 1,2-benzisothiazol-3-yl 998 1-methylindazol-3-yl 999 benzoxazol-2-yl 1000 5-chlorobenzoxazol-2-yl 20 1001 6-fluorobenzoxazol-2-yl 1002 benzthiazol-2-yl 1003 5-fluorobenzthiazol-2-yl 1004 6-fluorobenzthiazol-2-yl 1005 pyrido[3,2-d]thiazol-2-yl 1006 (6-chloropyrido)[3,2-dlthiazol-2-yl 1007 1-methyl-1,2,3-triazol-5-yl 1008 1-methyl-1,2,3-triazol-4-yl 1009 1-methyl-1,2,4-triazol-S-yl 30 1010 1-methyl-1,2,3,4-tetrazol-5-yl 1011 2-methyl-1,2,3,4-tetrazol-5-yl 1012 5-trifluoromethyl-1,3,4-thiA~i~zol-2-yl 1013 6-chlorobenzoxazol-2-yl 1014 5-fluorobenzoxazol-2-yl 1015 S-nitrothiazol-2-yl 1016 l-CH(CH3)2-pyrrol-3-y 1017 1-C(CH3)3-pyrrol-3-yl 1018 1-cyclopropylpyrrol-3-yl 1019 1-C6H5-pyrro1-3-yl 1020 1-(2-CH3-C6H4)pyrrol-3-yl 1021 l-(3-cH3-c6H4)pyrrol-3-yl 1022 1-(4-CH3-C6H4)pyrrol-3-yl 1023 1-(3-OCH3-C6H4)pyrrol-3-yl 1024 1-(4-OCH3-C6H4)pyrrol-3-yl 1025 1-(4-NO2-C6H4)pyrrol-3-yl No. R4 1026 1-(3-NO2-C6Hq)pyrrol-3-yl 1027 1-(4-CN-C6H4)pyrrol-3-yl 1028 1-(3-CN-C6H4)pyrrol-3-yl 1029 1-(3-CF3-C6H4)pyrrol-3-yl 1030 l-(4-cF3-c6H4)pyrrol-3-yl 1031 1-(4-CtCH3)3-C6H4)pyrrol-3-yl 10 1032 1-(2-Cl-C6H4)pyrrol-3-yl 1033 1-(3-Cl-C6H4)pyrrol-3-yl 1034 1-(4-Cl-C6H4)pyrrol-3-yl 1035 1-(2-Br-C6H4)pyrrol-3-yl 1036 1-(3-~r-C6H4)pyrrol-3-yl 1037 1-(4-~r-C6H4)pyrrol-3-yl 1038 1-(2-F-C6H4)pyrrol-3-yl 1039 1-(3-F-C6H4)pyrrol-3-yl 1040 1-(4-F-C6H4)pyrrol-3-yl 20 1041 1-(2,4-C12-C6H3)pyrrol-3-yl 1042 1-(2,5-C12-C6H3)pyrrol-3-yl 1043 1-(2,6-C12-C6H3)pyrrol-3-yl 1044 1-(3,4-C12-C6H3)pyrrol-3-yl 1045 1-(2,4-F2-C6H3)pyrrol-3-yl 1046 1-(2,5-F2-C6H3)pyrrol-3-yl 1047 1-(2,6-F2-C6H3)pyrrol-3-yl 1048 1-(3,4-F2-C6H3)pyrrol-3-yl 1049 1-(2-Cl, 5-OCH3-C6H3)pyrrol-3-yl 30 1050 1-(2-Cl, 5-CH3-C6H3)pyrrol-3-yl 1051 1-(5-Cl, 2-OCH3-C6H3)pyrrol-3-yl 1052 1-(5-Cl, 2-CH3-C6H3)pyrrol-3-yl 1053 1-[2,5-(CH3)2-C6H3]pyrrol-3-yl 1054 1-CH(CH3)2-pyrrol-2-yl 1055 1-C(CH3)3 PYLL~1_2_Y1 1056 1-cyclopropylpyrrol-2-yl 1057 1-C6H5-pyrrol-2-yl 1058 1-(2-CH3-C6H4)pyrrol-2-yl 40 1059 l-(3-cH3-c6H4)pyrrol-2 1060 l-(4-cH3-c6H4)pyrrol-2-yl 1061 1-(3-OCH3-C6H4)pyrrol-2-yl 1062 1-(4-OCH ff 6H4)pyrrol-2-yl 1063 l-(4-No2-c6H4)pyrrol-2 45 1064 1-(3-NO2-C6H4)pyrrol-2-yl 1065 1-(4-CN-C6H4)pyrrol-2-yl No. R4 1066 1-(3-CN-C6H4)pyrrol-2-yl 1067 1-(3-CF3-C6H4)pyrrol-2-yl 1068 1-(4-CF3-C6H4)pyrrol-2-yl 1069 1-(4-C(CH3)3-C6H4)pyrrol-2-yl 1070 1-(2-Cl-C6H4)pyrrol-2-yl 1071 1-(3-Cl-C6H4)pyrrol-2-yl 10 1072 1-(4-Cl-C6H4)pyrrol-2-yl 1073 1-(2-Br-C6H4)pyrrol-2-yl 1074 1-(3-Br-C6H4)pyrrol-2-yl 1075 1-(4-Br-C6H4)pyrrol-2-yl 1076 1-(2-F-C6H4)pyrrol-2-yl 1077 1-(3-F-C6H4)pyrrol-2-yl 1078 1-(4-F-C6H4)pyrrol-2-yl 1079 1-(2,4-C12-C6H3)pyrrol-2-yl 1080 1-(2,5-C12-C6H3)pyrrol-2-yl 20 1o8l 1-(2,6-C12-C6H3)pyrrol-2-yl 1082 1-(3,4-C12-C6H3)pyrrol-2-yl 1083 1-(2,4-F2-C6H3)pyrrol-2-yl 1084 1-(2,5-F2-C6H3)pyrrol-2-yl 1085 1-(2,6-F2-C6H3)pyrrol-2-yl 25 1086 1-(3,4-F2-C6H3)pyrrol-2-yl 1087 1-(2-Cl, 5-OCH3-C6H3)pyrrol-2-yl 1088 1-(2-Cl, 5-CH3-C6H3)pyrrol-2-yl 1089 1-(5-Cl, 2-OCH3-C6H3)pyrrol-2-yl 30 1090 1-(5-Cl, 2-CH3-C6H3)pyrrol-2-yl 1091 1-l2,5-(CH3)2-C6H3~pyrrol-2-yl 1092 5-CH(CH3)2-furan-2-yl 1093 5-C(CH3)3-furan-2-yl 1094 5-cyclopropylfuran-2-yl 35 1095 5-C6H5-furan-2-yl 1096 5-(2-CH3-C6H4)furan-2-yl 1097 5-(3-CH3-C6H4)furan-2-yl 1098 5-(4-CH3-C6H4)furan-2-yl 40 1099 5-(3-OCH3-C6H4)furan-2-yl 1100 5-(4-OCH3-C6H4)furan-2-yl 1101 5-(4-NO2-C6H4)furan-2-yl 1102 5-(3-No2-c6H4)furan-2 1103 5-(4-CN-C6H4)furan-2-yl 45 1104 5-(3-cN-c6H4)furan-2-yl 1105 5-(3-CF3-C6H4)furan-2-yl CA 0223l66l l998-04-07 No. R4 1106 5-~4-CF3-C6H4)furan-2-yl 1107 5-~4-C~CH3)3-C6H4)furan-2-yl 1108 5-~4-C6H5-C6H4)furan-2-yl 1109 5-~2-Cl-C6H4)furan-2-yl 1110 5-~3-Cl-C6H4)furan-2-yl 1111 5-~4-Cl-C6H4)furan-2-yl 10 1112 5-~2-Br-C6H4)furan-2-yl 1113 5-~3-Br-C6H4)furan-2-yl 1114 5-~4-Br-C6H4)furan-2-yl 1115 5-~2-F-C6H4)furan-2-yl 1116 5-~3-F-C6H4)furan-2-yl 1117 5-~4-F-C6H4)furan-2-yl 1118 5-~2,4-Cl2-C6H3)furan-2-yl 1119 5-~2,5-Cl2-C6H3)furan-2-yl 1120 5-~2,6-Cl2-C6H3)furan-2-yl 20 1121 5-~3,4-Cl2-C6H3)furan-2-yl 1122 5-~2,4-F2-C6H3)furan-2-yl 1123 5-~2,5-F2-C6H3)furan-2-yl 1124 5-~2,6-F2-C6H3)furan-2-yl 1125 5-~3,4-F2-C6H3)furan-2-yl 1126 5-~2-Cl, 5-OCH3-C6H3)furan-2-yl 1127 5-~2-Cl, 5-CH3-C6H3)furan-2-yl 1128 5-(5-Cl, 2-OCH3-C6H3)furan-2-yl 1129 5-(5-Cl, 2-CH3-C6H3)furan-2-yl 30 1130 5-[2,5-(CH3)2-C6H3lfuran-2-yl 1131 4-CH~CH3)2-furan-2-yl 1132 4-C(CH3)3-furan-2-yl 1133 4-cyclopropylfuran-2-yl 1134 4-4 H5-furan-2-yl 35 1135 4-(2-CH3-C6H4)furan-2-yl 1136 4-~3-CH3-C6H4)furan-2-yl 1137 4-~4-CH3-C6H4)furan-2-yl 1138 4-~3-OCH3-C6H4)furan-2-yl 40 1139 4-~4-OCH3-C6H4)furan-2-yl 1140 4-~4-N02-C6H4)furan-2-yl 1141 4-~3-N02-C6H4)furan-2-yl 1142 4-~4-CN-C6H4)furan-2-yl 1143 4-~3-CN-C6H4)furan-2-yl 45 1144 4-~3-CF3-C6H4)furan-2-yl 1145 4-~4-CF3-C6H4)furan-2-yl No. R4 1146 4-(4-C(CH3)3-C6H4)furan-2-yl 1147 4-(Z-Cl-C6H4)furan-2-yl 1148 4-(3-Cl-C6H4)furan-2-yl 1149 4-(4-Cl-C6H4)furan-2-yl 1150 4-(2-Br-C6H4)furan-2-yl llSl 4-(3-Br-C6H4)furan-2-yl 10 1152 4-(4-Br-C6H4)furan-2-yl 1153 4-(2-F-C6H4)furan-2-yl 1154 4-(3-F-C6H4)furan-2-yl 1155 4-(4-F-C6H4)furan-2-yl 1156 4-(2,4-C12-C6H3)furan-2-yl 1157 4-(2,5-C12-C6H3)furan-2-yl 1158 4-(2~6-cl2-c6H3)furan-2-yl 1159 4-(3~4-C12-C6H3)furan-2-yl 1160 4-(2,4-F2-C6H3)furan-2-yl 20 1161 4-(2,5-F2-C6H3)furan-2-yl 1162 4-(2,6-F2-C6H3)furan-2-yl 1163 4-(3~4-F2-c6H3)furan-2-yl 1164 4-(2-Cl, 5-OCH3-C6H3)furan-2-yl 1165 4-(2-Cl, 5-CH3-C6H3)furan-2-yl 25 1166 4-(5-Cl, 2-OCH3-C6H3)furan-2-yl 1167 4-(5-Cl, 2-CH3-C6H3)furan-2-yl 1168 4-[2,5-(CH3)2-C6H3]furan-2-yl 1169 5-CH(CH3)2-thien-2-yl 30 1170 5-C(CH3)3-thien-2-yl 1171 5-cyclopropylthien-2-yl 1172 5-C6H5-thien-2-yl 1173 5-(2-CH3-C6H4)thien-2-yl 1174 5-(3-CH3-C6H4)thien-2-yl 35 1175 5-(4-CH3-C6H4)thien-2-yl 1176 5-(3-OCH3-C6H4)thien-2-yl 1177 5-(4-OCH3-C6H4)thien-2-yl 1178 5-(4-NO2-C6H4)thien-2-yl 40 1179 5-(3-No2-c6H4)thien-2 1180 5-(4-CN-C6H4)thien-2-yl 1181 5-(3-cN-c6H4)thien-2-yl 1182 5-(3-CF3-C6H4)thien-2-yl 1183 5-(4-CF3-C6H4)thien-2-yl 45 1184 5-(4-C(CH3)3-C6H4)thien-2-yl 1185 5-(2-Cl-C6H4)thien-2-yl 0050/4627 ~

No. R4 1186 5-(3-Cl-C6H4)thien-2-yl 1187 5-(4-Cl-C6H4)thien-2-yl 1188 5-(2-Br-C6H4)thien-2-yl 1189 5-(3-Br-C6H4)thien-2-yl 1190 5-(4-Br-C6H4)thien-2-yl 1191 5-(2-F-C6H4)thien-2-yl 10 1192 5-(3-F-C6H4)thien-2-yl 1193 5-(4-F-C6H4)thien-2-yl 1194 5-(2,4-C12-C6H3)thien-2-yl ll9S 5-(2,5-C12-C6H3)thien-2-yl 1196 5-(2,6-C12-C6H3)thien-2-yl 1197 5-~3,4-C12-C6H3)thien-2-yl 1198 5-(2,4-F2-C6H3)thien-2-yl 1199 5-(2,5-F2-C6H3)thien-2-yl 1200 5-(2,6-F2-C6H3)thien-2-yl 20 12ol 5-(3,4-F2-C6H3)thien-2-yl 1202 5-(2-Cl, 5-OCH3-C6H3)thien-2-yl 1203 5-(2-Cl, 5-CH3-C6H3)thien-2-yl 1204 5-(5-Cl, 2-OCH3-C6H3)thien-2-yl 1205 5-(5-Cl, 2-CH3-C6H3)thien-2-yl 25 1206 5-[2,5-(CH3)2-C6H3]thien-2-yl 1207 4-CH(CH3)2-thien-2-yl 1208 4-C(CH3~3-thien-2-yl 1209 4-cyclopropylthien-2-yl 30 1210 4-C6H5-thien-2-yl 1211 4-(2-CH3-C6H4)thien-2-yl 1212 4-(3-CH3-C6H4)thien-2-yl 1213 4-(4-CH3-C6H4)thien-2-yl 1214 4-(3-OCH3-C6H4)thien-2-yl 35 1215 4-(4-OCH3-C6Hq)thien-2-yl 1216 4-(4-NO2-C6H4)thien-2-yl 1217 4-(3-NO2-C6H4)thien-2-yl 1218 4-(4-CN-C6H4)thien-2-yl 40 1219 4-(3-CN-C6H4)thien-2-yl 1220 4-(3-CF3-C6H4)thien-2-yl 1221 4-(4-cF3-c6H4)thien-2-yl 1222 4-(4-C(CH3)3-C6H4)thien-2-yl 1223 4-(2-Cl-C6H4)thien-2-yl 45 1224 4-(3-Cl-C6H4)thien-2-yl 1225 4-(4-Cl-C6H4)thien-2-yl No. R4 1226 4-(2-Br-C6H4)thien-2-yl 1227 4-(3-Br-C6H4)thien-2-yl 1228 4-(4-Br-C6H4)thien-2-yl 1229 4-(2-F-C6H4)thien-2-yl 1230 4-(3-F-c6H4)thien-2 1231 4-(4-F-C6H4)thien-2-yl 10 1232 4-(2,4-C12-C6H3)thien-2-yl 1233 4-(2,5-C12-C6H3)thien-2-yl 1234 4-(2,6-C12-C6H3)thien-2-yl 1235 4-(3,4-Clz-C6H3)thien-2-yl 1236 4-(2,4-F2-C6H3)thien-2-yl 1237 4-(2,5-F2-C6H3)thien-2-yl 1238 4-(2,6-F2-C6H3)thien-2-yl 1239 4-(3~4-F ff 6H3)thien-2-yl 1240 4-(2-Cl, 5-OCH3-C6H3)thien-2-yl 20 1241 4-(2-Cl, 5-CH3-C6H3)thien-2-yl 1242 4-(5-Cl, 2-OCH3-C6H3)thien-2-yl 1243 4-(5-Cl, 2-CH3-C6H3)thien-2-yl 1244 4-[2,5-(CH3)2-C6H3]thien-2-yl 1245 2-CH3-thien-4-yl 25 1246 2-CH(CH3)2-thien-4-yl 1247 2-C(CH3)3-thien-4-yl 1248 2-cyclopropylthien-4-yl 1249 2-C6H5-thien-4-yl 30 1250 2-(2-cH3-c6H4)thien-4-yl 1251 2-~3-CH3-C6H4)thien-4-yl 1252 2-~4-CH3-C6H4)thien-4-yl 1253 2-~3-OCH3-C6H4)thien-4-yl 1254 2-(4-ocH3-c6H~)thien-4 35 1255 2-(4-NO2-C6H4)thien-4-yl 1256 2-(3-NO2-C6H4)thien-4-yl 1257 2-(4-cN-c6H4)thien-4 1258 2-(3-cN-c6H4)thien-4-yl 40 1259 2-(3-CF3-C6H4)thien-4-yl 1260 2-(4-cF3-c6H4)thien-4 1261 2-(4-c(cH3)3-c6H4)thien-4 1262 2-(2-Cl-C6H 4 ) thien-4-yl 1263 2-(3-Cl-C6H4)thien-4-yl 45 1264 2-(4-cl-c6H4)thien-4 1265 2-(2-Br-C6H4)thien-4-yl CA 0223l66l l998-04-07 No. R4 1266 2-(3-Br-C6H4)thien-4-yl 1267 2-(4-Br-C6H4)thien-4-yl 1268 2-(2-F-C6H4)thien-4-yl 1269 2-(3-F-C6H4)thien-4-yl 1270 2-(4-F-C6H4)thien-4-yl 1271 2-(2,4-Cl2-C6H3)thien-4-yl 10 1272 2-(2,5-Cl2-C6H3)thien-4-yl 1273 2-(2,6-Cl2-C6H3)thien-4-yl 1274 2-(3,4-Cl2-C6H3)thien-4-yl 1275 2-(2,4-F2-C6H3)thien-4-yl 1276 2-~2,5-F2-C6H3)thien-4-yl 1277 2-~2,6-F2-C6H3)thien-4-yl 1278 2-~3,4-F2-C6H3)thien-4-yl 1279 2-~2-Cl, 5-OCH3-C6H3)thien-4-yl 1280 2-~2-Cl, 5-CH3-C6H3)thien-4-yl 20 128l 2-~5-Cl, 2-OCH3-4 H3)thien-4-yl 1282 2-~5-Cl, 2-CH3-C6H3)thien-4-yl 1283 2-[2,5-~CH3)2-C6H3]thien-4-yl 1284 1-CH~CH3)2-pyrazol-4-yl 1285 1-C(CH3)3-pyrazol-4-yl 25 1286 1-cyclopropylpyrazol-4-yl 1287 1-C6Hs-pyrazol-4-yl 1288 1-~2-CH3-C6H4)pyrazol-4-yl 1289 1-~3-CH3-C6H4)pyrazol-4-yl 30 1290 1-~4-CH3-C6H4)pyrazol-4-yl 1291 1-~3-OCH3-C6H4)pyrazol-4-yl 1292 1-~4-OCH3-C6H4)pyrazol-4-yl 1293 1-~4-NO2-C6H4)pyrazol-4-yl 1294 1-~3-NO2-C6H4)pyrazol-4-yl 35 1295 1-~4-CN-C6H4)pyrazol-4-yl 1296 1-~3-CN-C6H4)pyrazol-4-yl 1297 1-~3-CF3-C6H4)pyrazol-4-yl 1298 1-~4-CF3-C6H4)pyrazol-4-yl 40 1299 1-~4-C~CH3)3-C6H4)pyrazol-4-yl 1300 1-~2-Cl-C6H4)pyrazol-4-yl 1301 1-~3-Cl-C6H4)pyrazol-4-yl 1302 1-~4-Cl-C6H4)pyrazol-4-yl 1303 l-~2-Br-C6H4)pyrazol-4-yl 45 1304 1-(3-Br-C6H4)pyrazol-4-yl 1305 l-(4-Br-C6H4)pyrazol-4-yl 0050/4627~

No. R4 1306 1-(2-F-C6H4)pyrazol-4-yl 1307 1-(3-F-C6H4)pyrazol-4-yl 1308 1-(4-F-C6H4)pyrazo1-4-yl 1309 1-(2,4-C12-C6H3)pyrazol-4-yl 1310 1-(2,5-C12-C6H3)pyrazol-4-yl 1311 1-(2,6-C12-C6H3)pyrazol-4-yl 10 1312 1-(3,4-C12-C6H3)pyrazol-4-yl 1313 1-(2,4-F2-C6H3)pyrazol-4-yl 1314 1-(2,5-F2-C6H3)pyrazol-4-yl 1315 1-(2,6-F2-C6H3)pyrazol-4-yl 1316 1-(3,4-F2-C6H3)pyrazol-4-yl 1317 1-(2-Cl, 5-OCH3-C6H3)pyrazol-4-yl 1318 1-(2-Cl, 5-CH3-C6H3)pyrazol-4-yl 1319 1-(5-Cl, 2-OCH3-C6H3)pyrazol-4-yl 1320 1-(5-Cl, 2-CH3-C6H3)pyrazol-4-yl 20 1321 1-[2,5-(CH3)2-C6H3]pyrazol-4-yl 1322 1-CH(CH3)2-pyrazol-3-yl 1323 1-C(CH3)3-pyrazol-3-yl 1324 1-cyclopropylpyrazol-3-yl 1325 1-C6Hs-pyrazol-3-yl 25 1326 1-(2-CH3-C6H4)pyrazol-3-yl 1327 1-(3-CH3-C6H4)pyrazol-3-yl 1328 1-(4-CH3-C6H4)pyrazol-3-yl 1329 1-(3-OCH3-C6H4)pyrazol-3-yl 30 1330 1-(4-OCH3-C6H4)pyrazol-3-yl 1331 1-(4-N02-C6H4)pyrazol-3-yl 1332 1-(3-N02-C6H4)pyrazol-3-yl 1333 1-(4-CN-C6H4)pyrazol-3-yl 1334 1-(3-CN-C6H4)pyrazol-3-yl 35 1335 1-(3-CF3-C6H4)pyrazol-3-yl 1336 l-(4-CF3-C6H4)pyrazol-3-yl 1337 1-(4-C(CH3)3-C6H4)pyrazol-3-yl 1338 1-(2-Cl-C6H4)pyrazol-3-yl 40 1339 1-(3-Cl-C6H4)pyrazol-3-yl 1340 l-(4-cl-c6H4)pyrazol-3 1341 1-(2-Br-C6H4)pyrazol-3-yl 1342 1-(3-Br-C6H4)pyrazol-3-yl 1343 1-(4-Br-C6H4)pyrazol-3-yl 45 1344 1-(2-F-C6H4)pyrazol-3-yl 1345 1-(3-F-C6H4)pyrazol-3-yl No. R4 1346 1-~4-F-C6H4)pyrazol-3-yl 1347 1-(2,4-C12-C6H3)pyrazol-3-yl 1348 1-(2,5-Cl2-C6H3)pyrazol-3-yl 1349 1-(2,6-C12-C6H3)pyrazol-3-yl 1350 1-(3,4-C12-C6H3)pyrazol-3-yl 1351 1-(2,4-F2-C6H3)pyrazol-3-yl 1352 1-(2,5-F2-C6H3)pyrazol-3-yl 1353 1-(2,6-F2-C6H3)pyrazol-3-yl 1354 1-(3,4-F2-C6H3)pyrazol-3-yl 1355 1-(2-Cl, S-OCH3-C6H3)pyrazol-3-yl 1356 1-(2-Cl, 5-CH3-C6H3)pyrazol-3-yl 1357 1-(5-Cl, 2-OCH3-C6H3)pyrazol-3-yl 1358 1-(5-Cl, 2-CH3-C6H3)pyrazol-3-yl 1359 1-[2,5-(CH3)2-C6H3lpyrazol-3-yl 1360 3-CH(CH3)2-isoxazol-5-yl 1361 3-C(CH3)3-isoxazol-5-yl 1362 3-cyclopropylisoxazol-5-yl 1363 3-C6Hs-isoxazol-5-yl 1364 3-(2-CH3-C6H4)isoxazol-5-yl 1365 3-(3-cH3-c6H4)isoxazol-5-yl 1366 3-(4-CH3-C6H4)isoxazol-5-yl 1367 3-(3-OCH3-C6H4)isoxazol-5-yl 1368 3-(4-OCH3-C6H4)isoxazol-5-yl 1369 3-(4-NO2-C6H4)isoxazol-5-yl 30 1370 3-(3-NO2-C6H4)isoxazol-5-yl 1371 3-(4-CN-C6H4)isoxazol-5-yl 1372 3-(3-CN-C6H4)isoxazol-5-yl 1373 3-(3-CF3-C6H4)isoxazol-5-yl 1374 3-(4-CF3-C6H4)isoxazol-5-yl 35 1375 3-(4-C(CH3)3-C6H4)isoxazol-5-yl 1376 3-(2-Cl-C6H4)isoxazol-5-yl 1377 3-(3-Cl-C6H4)isoxazol-5-yl 1378 3-(4-Cl-C6H4)isoxazol-5-yl 40 1379 3-(2-Br-C6H4)isoxazol-5-yl 1380 3-(3-Br-C6H4)isoxazol-5-yl 1381 3-(4-~r-C6H4)isoxazol-5-yl 1382 3-(2-F-C6H4)isoxazol-5-yl 1383 3-(3-F-C6H4)isoxazol-5-yl 45 1384 3-(4-F-C6H4)isoxazol-5-yl 1385 3-(2,4-Cl2-C6H3)isoxazol-5-yl No. R4 1386 3-(2,5-Cl2-C6H3)isoxazol-5-yl 1387 3-(2,6-C12-C6H3)isoxazol-5-yl 1388 3-(3,4-C12-C6H3)isoxazol-5-yl 1389 3-(2,4-F2-C6H3)isoxazol-5-yl 1390 3-(2,5-F2-C6H3)isoxazol-5-yl 1391 3-(2,6-F2-C6H3)isoxazol-5-yl 10 1392 3-(3,4-F2-C6H3)isoxazol-5-yl 1393 3-(2-Cl, 5-OCH3-C6H3)isoxazol-5-yl 1394 3-(2-Cl, 5-CH3-C6H3)isoxazol-5-yl 1395 3-(5-Cl, 2-OCH3-C6H3)isoxazol-5-yl 1396 3-(5-Cl, 2-CH3-C6H3)isoxazol-5-yl 1397 3-[2,5-(CH3)2-C6H3]isoxazol-5-yl 1398 5-CH(CH3)2-isoxazol-3-yl 1399 5-C(CH3)3-isoxazol-3-yl 1400 5-cyclopropylisoxazol-3-yl 20 1401 5-C6H5-isoxazol-3-yl 1402 5-(2-CH3-C6H4)isoxazol-3-yl 1403 5-(3-CH3-C6H4)isoxazol-3-yl 1404 5-(4-CH3-C6H4)isoxazol-3-yl 1405 5-(3-OCH3-C6H4)isoxazol-3-yl 25 1406 5-(4-OCH3-C6H4)isoxazol-3-yl 1407 5-(4-NO2-C6H4)isoxazol-3-yl 1408 5-(3-NO2-C6H4)isoxazol-3-yl 1409 5-(4-CN-C6H4)isoxazol-3-yl 30 1410 5-(3-CN-C6H4)isoxazol-3-yl 1411 5-(3-CF3-C6H4)isoxazol-3-yl 1412 5-(4-CF3-C6H4)isoxazol-3-yl 1413 5-(4-C(CH3)3-C6H4)isoxazol-3-yl 1414 5-(2-Cl-C6H4)isoxazol-3-yl 35 1415 5-(3-Cl-C6H4)isoxazol-3-yl 1416 5-(4-Cl-C6H4)isoxazol-3-yl 1417 5-(2-Br-C6H4)isoxazol-3-yl 1418 5-(3-Br-C6H4)isoxazol-3-yl 40 1419 5-(4-Br-C6H4)isoxazol-3-yl 1420 5-(2-F-C6H4)isoxazol-3-yl 1421 5-(3-F-C6H4)isoxazol-3-yl 1422 5-(4-F-C6H4)isoxazol-3-yl 1423 5-(2,4-Cl2-C6H3)isoxazol-3-yl 45 1424 5-(2,5-C12-C6H3)isoxazol-3-yl 1425 5-(2,6-C12-C6H3)isoxazol-3-yl No. R4 1426 5-(3,4-C12-C6H3)isoxazol-3-yl 1427 5-(2,4-F2-C6H3)isoxazol-3-yl 1428 5-(2,5-F2-C6H3)isoxazol-3-yl 1429 5-(2,6-F2-C6H3)isoxazol-3-yl 1430 5-(3,4-F2-C6H3)isoxazol-3-yl 1431 5-(2-Cl, 5-OCH3-C6H3)isoxazol-3-yl 10 1432 5-(2-Cl, 5-CH3-C6H3)isoxazol-3-yl 1433 5-(5-Cl, 2-OCH3-C6H3)isoxazol-3-yl 1434 S-(S-Cl, 2-CH3-C6H3)isoxazol-3-yl 1435 5-[2,5-(CH3)2-C6H3]isoxazol-3-yl 1436 3-CH(CH3)2-isothiazol-S-yl 1437 3-C(CH3)3-isothiazol-5-yl 1438 3-cyclopropylisothiazol-S-yl 1439 3-C6H5-isothiazol-S-yl 1440 3-(2-CH3-C6H4)isothiazol-S-yl 20 1441 3-(3-CH3-C6H4)isothiazol-S-yl 1442 3-(4-CH3-C6H4)isothiazol-S-yl 1443 3-(3-OCH3-C6H4)isothiazol-S-yl 1444 3-(4-OCH3-C6H4)isothiazol-S-yl 1445 3-(4-N02-C6H4)isothiazol-S-yl 1446 3-(3-N02-C6H4)isothiazol-S-yl 1447 3-(4-CN-C6H4)isothiazol-S-yl 1448 3-(3-CN-C6H4)isothiazol-5-yl 1449 3-(3-CF3-C6H4)isothiazol-S-yl 30 1450 3-(4-CF3-C6H4)isothiazol-S-yl 1451 3-(4-C(CH3)3-C6H4)isothiazol-S-yl 1452 3-(2-Cl-C6H4)isothiazol-S-yl 1453 3-(3-Cl-C6H4)isothiazol-S-yl 1454 3-(4-Cl-C6H4)isothiazol-S-yl 35 1455 3-(2-Br-C6H4)isothiazol-S-yl 1456 3-(3-Br-C6H4)isothiazol-S-yl 1457 3-(4-Br-C6H4)isothiazol-5-yl 1458 3-(2-F-C6H4)isothiazol-5-yl 40 1459 3-(3-F-C6H4)isothiazol-5-yl 1460 3-(4-F-C6H4)isothiazol-5-yl 1461 3-(2,4-C12-C6H3)isothiazol-5-yl 1462 3-(2,5-C12-C6H3)isothiazol-5-yl 1463 3-(2~6-Cl2-C6H3)isothiazol-5-yl 45 1464 3-(3,4-C12-C6H3)isothiazol-5-yl 1465 3-(2,4-F2-C6H3)isothiazol-5-yl No. R4 1466 3-(2,5-F2-C6H3)isothiazol-5-yl 1467 3-(2,6-F2-C6H3)isothiazol-5-yl 1468 3-(3,4-F2-C6H3)isothiazol-5-yl 1469 3-~2-Cl, 5-OCH3-C6H3)isothiazol-5-yl 1470 3-(2-Cl, 5-CH3-C6H3)isothiazol-5-yl 1471 3-(5-Cl, 2-OCH3-C6H3)isothiazol-5-yl 10 1472 3-(5-Cl, 2-CH3-C6H3)isothiazol-5-yl 1473 3-[2,5-(CH3)2-C6H3]isothiazol-5-yl 1474 2-CH(CH3)2-oxazol-4-yl 1475 2-C(CH3)3-oxazol-4-yl 1476 2-cyclopropyloxazol-4-yl 1477 2-C6H5-oxazol-4-yl 1478 2-(2-CH3-C6H4)oxazol-4-yl 1479 2-(3-CH3-C6H4)oxazo1-4-yl 1480 2-(4-CH3-C6H4)oxazol-4-yl 20 148l 2-(3-OCH3-C6H4)oxazol-4-yl 1482 2-(4-OCH3-C6H4)oxazol-4-yl 1483 2-(4-N02-C6H4)oxazol-4-yl 1484 2-(3-N02-C6H4)oxazol-4-yl 1485 2-(4-CN-C6H4)oxazol-4-yl 25 1486 2-(3-CN-C6H4)oxazol-4-yl 1487 2-(3-CF3-C6H4)oxazol-4-yl 1488 2-(4-CF3-C6H4)oxazol-4-yl 1489 2-(4-C(CH3)3-C6H4)0xazol-4-yl 30 1490 2-(2-Cl-C6H4)oxazol-4-yl 1491 2-(3-Cl-C6H4)oxazol-4-yl 1492 2-(4-Cl-C6H4)oxazol-4-yl 1493 2-(2-Br-C6H4)oxazol-4-yl 1494 2-(3-Br-C6H4)oxazol-4-yl 35 1495 2-(4-Br-C6H4)oxazol-4-yl 1496 2-(2-F-C6H4)oxazol-4-yl 1497 2-(3-F-C6H4)oxazol-4-yl 1498 2-(4-F-C6H4)oxazol-4-yl 40 1499 2-(2,4-Cl2-C6H3)oxazol-4-yl 1500 2-(2,5-C12-C6H3)oxazol-4-yl 1501 2-(2,6-C12-C6H3)oxazol-4-yl 1502 2-(3,4-Cl2-C6H3)oxazol-4-yl 1503 2-(2,4-F2-C6H3)oxazol-4-yl 45 1504 2-(2,5-F2-C6H3)oxazol-4-yl 1505 2-(2,6-F2-C6H3)oxazol-4-yl No. R4 1506 2-(3,4-F2-C6H3)0xazol-4-yl lS07 2-(2-Cl, S-OCH3-C6H3)oxazol-4-yl lS08 2-(2-Cl, S-CH3-C6H3)0xazol-4-yl 1509 2-(5-Cl, 2-OCH3-C6H3)0xazol-4-yl 1510 2-(5-Cl, 2-CH3-C6H3)oxazol-4-yl lSll 2-[2,5-(CH3)2-C6H3]oxazol-4-yl 10 1512 2-CH(CH3)2-thiazol-4-yl 1513 2-C(CH3)3-thiazol-4-yl 1514 2-cyclopropylthiazol-4-yl 1515 2-C6H5-thiazol-4-yl 1516 2-(2-CH3-C6H4)thiazol-4-yl 1517 2-(3-CH3-C6H4)thiazol-4-yl 1518 2-(4-cH3-c6H4)thiazol-4-yl lS19 2-(3-OCH3-C6H4)thiazol-4-yl lS20 2-(4-OCH3-C6H4)thiazol-4-yl 20 lS21 2-(4-N02-C6H4)thiazol-4-yl lS22 2-(3-N02-C6H4)thiazol-4-yl 1523 2-(4-CN-C6H4)thiazol-4-yl 1524 2-(3-CN-C6H4)thiazol-4-yl 1525 2-(3-CF3-C6H4)thiazol-4-yl 25 1526 2-(4-CF3-C6H4)thiazol-4-yl 1527 2-(4-C(CH3)3-C6H4)thiazol-4-yl lS28 2-(2-Cl-C6H4)thiazol-4-yl lS29 2-(3-Cl-C6H4)thiazol-4-yl 30 lS30 2-(4-Cl-C6H4)thiazol-4-yl lS31 2-(2-Br-C6H4)thiazol-4-yl lS32 2-(3-Br-C6H4)thiazol-4-yl lS33 2-(4-Br-C6H4)thiazol-4-yl lS34 2-(2-F-C6H4)thiazol-4-yl 35 lS3S 2-(3-F-C6H4)thiazol-4-yl lS36 2-(4-F-C6H4)thiazol-4-yl lS37 2-(2,4-C12-C6H3)thiazol-4-yl lS38 2-(2,S-C12-C6H3)thiazol-4-yl 40 lS39 2-(2,6-C12-C6H3)thiazol-4-yl lS40 2-(3~4-cl2-c6H3)thiazol-4 lS41 2-(2,4-F2-C6H3)thiazol-4-yl lS42 2-(2~5-F2-c6H3)thiazol-4 1543 2-(2,6-F2-C6H3)thiazol-4-yl 45 1544 2-(3,4-F2-C6H3)thiazol-4-yl lS4S 2-(2-Cl, 5-OCH3-C6H3)thiazol-4-yl No. R4 1546 2-(2-Cl, 5-CH3-C6H3)thiazol-4-yl 1547 2-(5-Cl, 2-OCH3-C6H3)thiazol-4-yl 1548 2-(5-Cl, 2-CH3-C6H3)thiazol-4-yl 1549 2-[2,5-(CH3)2-C6H3]thiazol-4-yl 1550 l~3-(cH3)2-l~2~4-triazol-5-yl 1551 1-CH(CH3)2-1,2,4-triazol-3-yl 1552 1-C(CH3)3-1,2,4-triazol-3-yl 1553 1-cyclopropyl-1,2,4-triazol-3-yl 1554 1-C6H5-1,2,4-triazol-3-yl 1555 1-(2-CH3-C6H4)-1,2,4-triazol-3-yl 1556 l-(3-cH3-c6H4)-l~2~4-triazol-3-yl 1557 1-(4-CH3-C6H4)-1,2,4-triazol-3-yl 1558 1-(3-OCH3-C6H4)-1,2,4-triazol-3-yl 1559 1-(4-OCH3-C6H4)-1,2,4-triazol-3-yl 1560 1-(4-N02-C6H4)-1,2,4-triazol-3-yl 156l 1-(3-N02-C6H4)-1,2,4-triazol-3-yl 1562 1-(4-CN-C6H4)-1,2,4-triazol-3-yl 1563 1-(3-CN-C6H4)-1,2,4-triazol-3-yl 1564 1-(3-CF3-C6H4)-1,2,4-triazol-3-yl 1565 1-(4-CF3-C6H4)-1,2,4-triazol-3-yl 1566 1-(4-C(CH3)3-C6H4)-1,2,4-triazol-3-yl 1567 1-(4-C6H5-C6H4)-1,2,4-triazol-3-yl 1568 1-(2-Cl-C6H4)-1,2,4-triazol-3-yl 1569 l-(3-cl-c6H4)-l~2~4-triazol-3-yl 1570 l-(4-Cl-C6H4)-1,2,4-triazol-3-yl 1571 1-(2-Br-C6H4)-1,2,4-triazol-3-yl 1572 1-(3-Br-C6H4)-1,2,4-triazol-3-yl 1573 1-(4-Br-C6H4)-1,2,4-triazol-3-yl 1574 1-(2-F-C6H4)-1,2,4-triazol-3-yl 35 1575 1-(3-F-C6H4)-1,2,4-triazol-3-yl 1576 1-(4-F-C6H4)-1,2,4-triazol-3-yl 1577 1-(2,4-C12-C6H3)-1,2,4-triazol-3-yl 1578 1-(2,5-C12-C6H3)-1,2,4-triazol-3-yl 40 1579 l-(2~6-cl2-c6H3)-l~2~4-triazol-3 1580 l-(3~4-cl2-c6H3)-l~2~4-triazol-3 1581 1-(2,4-F2-C6H3)-1,2,4-triazol-3-yl 1582 1-(2,5-F2-C6H3)-1,2,4-triazol-3-yl 1583 l-(2,6-F2-C6H3)-1,2,4-triazol-3-yl 45 1584 1-(3,4-F2-C6H3)-1,2,4-triazol-3-yl 1585 1-(2-Cl, 5-OCH3-C6H3)-1,2,4-triazol-3-yl No. R4 1586 1-(2-Cl, 5-CH3-C6H3)-1,2,4-triazol-3-yl 1587 1-(5-Cl, 2-OCH3-C6H3)-1,2,4-triazol-3-yl 1588 1-(5-Cl, 2-CH3-C6H3)-1,2,4-triazol-3-yl 1589 l-[2~5-(cH3)2-c6H3]-l~2~4-triazol-3 1590 5-C(CH3)3-1,3,4-oxadiazol-2-yl 1591 5-cyclopropyl-1,3,4-oxadiazol-2-yl 1592 5-C6Hs-1,3,4 ox~A.~iAzol-2-yl 1593 5-(2-CH3-C6H4)-1,3,4-oxadiazol-2-yl 1594 5-(3-CH3-C6H4)-1,3,4-oxadiazol-2-yl 1595 5-(4-CH3C6H4)-1,3,4-oxadiazol-2-yl 1596 5-(3-OCH3C6H4)-1,3,4- OyA~ i A zol - 2-yl 1597 5-(4-OCH3C6H4)-1,3,4- OYA~ i A zol-2-yl 1598 5-(4-NO2-C6H4)-1,3,4-oxadiazol-2-yl 1599 5-(3-NO2-C6H4)-1,3,4-oxadiazol-2-yl 1600 5-(4-CN-C6H4)-1,3,4- OY~A,~ i A 7O1-2-yl 20 1601 5-(3-CN-C6H4)-1,3,4- OyA~ i A 701 - 2-yl 1602 5-(3-CF3C6H4)-1,3,4 - OXA~ i A 7O1-2-yl 1603 5-(4 CF3C6H4)-1,3~4 OyA~ i ,A zol-2-yl 1604 5-(4-C(CH3)3C6H4)-1,3,4-oxadiazol-2-yl 1605 5-(2-Cl-C6H4)-1,3,4-oxadiazol-2-yl 1606 5-(3-Cl-C6H4)-1,3,4-oYA~iAzol-2-yl 1607 5-(4-Cl-C6H4)-1,3,4-oxadiazol-2-yl 1608 5-(2-Br-C6H4)-1,3,4-oYAAiAzol-2-yl 1609 5-(3-Br-C6H4)-1,3,4-oY~i A 7.01-2-yl 30 1610 5-(4-Br-C6H4)-1,3,4-oxadiazol-2-yl 1611 5-(2-F-C6H4)-1,3,4-oYA~iazol-2-yl 1612 5-(3-F-C6H4)-1,3,4-oY~ zol-2-yl 1613 5-(4-F-C6H4)-1,3,4-oY~iAzol-2-yl 1614 5-(2,4-C12-C6H3)-1,3,4- OyA~ i A 7O1-2-yl 35 1615 5-(2,5-Cl2-C6H3)-1,3,4-oY~iA701-2-yl 1616 5-(2,6-C12-C6H3)-1,3,4-oxadiazol-2-yl 1617 5-(3,4-C12-C6H3)-1,3,4-oxadiazol-2-yl 1618 5-(2,4-F2-C6H3)-1,3,4-oxadiazol-2-yl 40 1619 5-(2,5-F2-C6H3)-1,3,4-oxadiazol-2-yl 1620 5-(2,6-F2-C6H3)-1,3,4-oxadiazol-2-yl 1621 5-(3,4-F2-C6H3)-1,3,4-oxadiazol-2-yl 1622 5-(2-Cl, 5-OCH3C6H3)-1,3,4-oxadiazol-2-yl 1623 5-(2-Cl, 5-CH3C6H3)-1,3,4-oxadiazol-2-yl 45 1624 5-(5-Cl, 2-OCH3C6H3)-1,3,4-oxadiazol-2-yl 1625 5-(5-Cl, 2-CH3C6H3)-1,3,4-oxadiazol-2-yl CA 0223l66l l998-04-07 No. R4 1626 5-[2,5-(CH3)2-C6H3]-1,3,4-oxadiazol-2-yl 1627 5-C(CH3)3-1,2,4-oxadiazol-3-yl 1628 5-cyclopropyl-1,2,4-oxadiazol-3-yl 1629 5-C6Hs-1,2,4-oxadiazol-3-yl 1630 5-(2-CH3C6H4)-1,2,4-oxadiazol-3-yl 1631 5-(3-CH3C6H4)-1,2,4-oxa~iazol-3-yl 1632 5-(4-CH3C6H4)-1,2,4-oxadiazol-3-yl 1633 5-(3-OCH3C6H4)-1,2,4-oxadiazol-3-yl 1634 5-(4-OCH3C6H4)-1,2,4-oxadiazol-3-yl 1635 5-(4-NO2-C6H4)-1,2,4-oxadiazol-3-yl 1636 5-(3-NO2-C6H4)-1,2,4-oxadiazol-3-yl 1637 5-(4-CN-C6H4)-1,2,4-oxadiazol-3-yl 1638 5-(3-CN-C6H4)-1,2,4-oYA~i~zol-3-yl 1639 5-(3-CF3-C6H4)-1,2,4-oxadiazol-3-yl 1640 5-(4-CF3-C6H4)-1,2,4-oY~A~iA7.ol-3-yl 164l 5-(4-C(CH3)3C6H4)-1,2,4-oxadiazol-3-yl 1642 5-(2-Cl-C6H4)-1,2,4-oxA~i~zol-3-yl 1643 5-(3-Cl-C6H4)-1,2,4-oxadiazol-3-yl 1644 5-(4-Cl-C6H4)-1,2,4-oxa~iazol-3-yl 1645 5-(2-Br-C6H4)-1,2,4-oxadiazol-3-yl 1646 5-(3-Br-C6H4)-1,2,4-oxA~ia7ol-3-yl 1647 5-(4-Br-C6H4)-1,2,4-oxadiazol-3-yl 1648 5-(2-F-C6H4)-1,2,4-oxadiazol-3-yl 1649 5-(3-F-C6H4)-1,2,4-oxadiazol-3-yl 1650 5-(4-F-C6H4)-1,2,4-oxadiazol-3-yl 1651 5-(2,4-Cl2-C6H3)-1,2,4- oXA~i A701-3-yl 1652 5-(2,5-Cl2-C6H3)-1,2,4-oxadiazol-3-yl 1653 5-(2,6-Cl2-C6H3)-1,2,4-oxadiazol-3-yl 1654 5-(3,4-Cl2-C6H3)-1,2,4-oxadiazol-3-yl 1655 5-(2,4-F2-C6H3)-1,2,4-oYa~i~Azol-3-yl 1656 5-(2,5-F2-C6H3)-1,2,4-oxadiazol-3-yl 1657 5-(2,6-F2-C6H3)-1,2,4-ox~-a7.01-3-yl 1658 5-(3~4-F2-c6H3)-l~2~4-oxadiazol-3-yl 1659 5-(2-Cl, 5-OCH3C6H3)-1,2,4-oxadiazol-3-yl 1660 5-(2-Cl, 5-CH3C6H3)-1,2,4-oxadiazol-3-yl 1661 5-(5-Cl, 2-OCH3C6H3)-1,2,4-oxadiazol-3-yl 1662 5-(5-Cl, 2-CH3C6H3)-1,2,4-oxadiazol-3-yl 1663 5-[2,5-(CH3)2-C6H3]-1,2,4-oxadiazol-3-yl 1664 3-CH3-1,2,4-oxadiazol-5-yl 1665 3-CH(CH3)2-1,2,4-oxadiazol-5-yl No. R4 1666 3-C~CH3)3-1,2,4-oxadiazol-5-yl 1667 3-cyclopropyl-1,2,4-oxadiazol-5-yl 1668 3-C6Hs-1,2,4-oxadiazol-5-yl 1669 3-(2-CH3C6Hq)-1,2,4-oxadiazol-5-yl 1670 3-(3-CH3C6H4)-1,2,4-oxadiazol-5-yl 1671 3-(4-CH3C6H4)-1,2,4-oxadiazol-5-yl 10 1672 3-(3-OCH3C6H4)-1,2,4-oxadiazol-5-yl 1673 3-(4-OCH3C6H4)-1,2,4-oxadiazol-5-yl 1674 3-(4-NO2-C6H4)-1,2,4-oxadiazol-5-yl 1675 3-(3-NO2-C6H4)-1,2,4-oxadiazol-5-yl 1676 3-(4-CN-C6H4)-1,2,4-oxadiazol-5-yl 1677 3-(3-CN-C6H4)-1,2,4- OyA~; A701 - 5-yl 1678 3-(3-CF3-C6H4)-1,2,4-oYA~;A7ol-5-yl 1679 3-(4-CF3-C6H4)-1,2,4-oxadiazol-5-yl 1680 3-(4-c(cH3)3c6H4)-l~2~4-oyA~iAzol-5 20 1681 3-(2-Cl-C6H4)-1,2,4-oYA.~;A7ol-5-yl 1682 3-(3-Cl-C6H4)-1,2,4-oxadiazol-5-yl 1683 3-(4-Cl-C6H4)-1,2,4-oxadiazol-5-yl 1684 3-(2-Br-C6H4)-1,2,4-oxadiazol-5-yl 1685 3-(3-Br-C6H4)-1,2,4-sY~;Azol-5-yl 1686 3-(4-Br-C6H4)-1,2,4- OYA~; A 701 - 5 - yl 1687 3-(2-F-C6H4)-1,2,4-oYAAiA7ol-s-yl 1688 3-(3-F-C6H4)-1,2,4-oYA~;A.7ol-5-yl 1689 3-(4-F-C6H4)-1,2,4-oYa~;P701-5-yl 30 1690 3-(2,4-Cl2-C6H3)-1,2,4-oYA~;A701-5-yl 1691 3-(2,5-Cl2-C6H3)-1,2,4-oY~;A701-5-yl 1692 3-(2,6-C12-C6H3)-1,2,4-oYA~;Azol-5-yl 1693 3-(3,4-C12-C6H3)-1,2,4-oY~A~iAzol-5-yl 1694 3-(2,4-F2-C6H3)-1,2,4-oxadiazol-5-yl 1695 3-(2,5-F2-C6H3)-1,2,4-oYA~;A7ol-5-yl 1696 3-(2,6-F2-C6H3)-1,2,4-oYA~;A7ol-5-yl 1697 3-(3,4-F2-C6H3)-1,2,4-oxadiazol-5-yl 1698 3-(2-Cl, 5-OCH3C6H3)-1,2,4-oxadiazol-5-yl 40 1699 3-(2-Cl, 5-CH3-C6H3)-1,2,4-oxadiazol-5-yl 1700 3-(5-Cl, 2-OCH3-C6H3)-1,2,4-oxadiazol-5-yl 1701 3-(5-Cl, 2-CH3-C6H3)-1,2,4-oxadiazol-5-yl 1702 3-[2,5-(CH3)2-C6H3]-1,2,4-oxadiazol-5-yl 1703 5-CH3-1,2,4-thiadiazol-3-yl 45 1704 5-cH(cH3)2-l~2~4-thiadiazol-3 1705 5-C(CH3)31,2,4-thiadiazol-3-yl CA 0223l66l l998-04-07 No. R4 1706 S-cyclopropyl-1,2,4-thiadiazol-3-yl 1707 5-C6H5-1,2,4-thiadiazol-3-yl 1708 5-(2-CH3-C6H4)-1,2,4-~h;A~i~zol-3-yl 1709 5-(3-CH3-C6H4)-1,2,4-thiadiazol-3-yl 1710 5-(4-CH3-C6H4)-1,2,4-thiadiazol-3-yl 1711 5-(3-OCH3-C6H4)-1,2,4-thiadiazol-3-yl 10 1712 5-(4-OCH3-C6H4)-1,2,4-thiadiazol-3-yl 1713 5-(4-NO2-C6H4)-1,2,4-thiadiazol-3-yl 1714 5-(3-NO2-C6H4)-1,2,4-thiadiazol-3-yl 1715 5-(4-CN-C6H4)-1,2,4-thiadiazol-3-yl 1716 5-(3-CN-C6H4)-1,2,4-thiadiazol-3-yl 1717 5-(3-CF3-C6H4)-1,2,4-thiadiazol-3-yl 1718 5-(4-CF3-C6H4)-1,2,4-thiadiazol-3-yl 1719 5-(4-C(CH3)3-C6H4)-1,2,4-thiA~;azol-3-yl 1720 5-(2-Cl-C6H4)-1,2,4-thiadiazol-3-yl 20 1721 5-(3-Cl-C6H4)-1,2,4-thiadiazol-3-yl 1722 5-(4-Cl-C6H4)-1,2,4-thiadiazol-3-yl 1723 5-(2-Br-C6H4)-1,2,4-thiadiazol-3-yl 1724 5-(3-Br-C6H4)-1,2,4-thiA~;Azol-3-yl 1725 5-(4-Br-C6H4)-1,2,4-thiadiazol-3-yl 25 1726 5-(2-F-C6H4)-1,2,4-thiadiazol-3-yl 1727 5-(3-F-C6H4)-1,2,4-~hi ,A~i ,AZOl - 3 - yl 1728 5-(4-F-C6H4)-1,2,4-thiadiazol-3-yl 1729 5-(2,4-Cl2-C6H3)-1,2,4-~hi-AdiAzol-3 30 1730 5-(2,5-Cl2-C6H3)-1,2,4-~hi A~ i A z.ol-3-yl 1731 5-(2,6-Cl2-C6H3)-1,2,4-thi A~ i A zol-3-yl 1732 5-(3,4-Cl2-C6H3)-1,2,4-thiadiazol-3-yl 1733 5-(2,4-F2-C6H3)-1,2,4-thiadiazol-3-yl 1734 5-(2,5-F2-C6H3)-1,2,4-thiadiazol-3-yl 35 1735 5-(2,6-F2-C6H3)-1,2,4-thiadiazol-3-yl 1736 5-(3,4-F2-C6H3)-1,2,4-thiadiazol-3-yl 1737 5-(2-Cl, 5-OCH3-C6H3)-1,2,4-thiadiazol-3-yl 1738 5-(2-Cl, 5-CH3-C6H3)-1,2,4-thiadiazol-3-yl 40 1739 5-(5-Cl, 2-OCH3-C6H3)-1,2,4-thiadiazol-3-yl 1740 5-(5-Cl, 2-CH3-C6H3)-1,2,4-thiadiazol-3-yl 1741 5-[2,5-(CH3)2-C6H3]-1,2,4-thiadiazol-3-yl 1742 5-CH3-1,3,4-thiadiazol-2-yl 1743 5-CH(CH3) 2- 1, 3,4-thiadiazol-2-yl 45 1744 5-C(CH3)3-1,3,4-thiadiazol-2-yl 1745 5-cyclopropyl-1,3,4-thiadiazol-2-yl No. R4 1746 5-C6H5-1,3,4-th;~ 701-2-yl 1747 5-(2-CH3-C6H4)-1,3,4-thiadiazol-2-yl 1748 5-(3-CH3-C6H4)-1,3,4-thiadiazol-2-yl 1749 5-(4-CH3-C6H4)-1,3,4-thiadiazol-2-yl 1750 5-(3-OCH3-C6H4)-1,3,4-thiadiazol-2-yl 1751 5-(4-OCH3-C6H4)-1,3,4-thiadiazol-2-yl 10 1752 5-(4-N02-C6H4)-1,3,4-thiadiazol-2-yl 1753 5-(3-NO2-C6H4)-1,3,4-thiadiazol-2-yl 1754 5-(4-CN-C6H4)-1,3,4-thiadiazol-2-yl 1755 5-(3-CN-C6H4)-1,3,4-thiadiazol-2-yl 1756 5-(3-CF3-C6H4)-1,3,4-thiadiazol-2-yl 1757 5-(4-CF3-C6H4)-1,3,4-thiadiazol-2-yl 1758 5-(4-C(CH3)3-C6H4)-1,3,4-thiadiazol-2-yl 1759 5-(2-Cl-C6H4)-1,3,4-thiadiazol-2-yl 1760 5-(3-Cl-C6H4)-1,3,4-thi A~i A zol-2-yl 20 1761 5-(4-Cl-C6H4)-1,3,4-~hi~iA7ol-2-yl 1762 5-(2-Br-C6H4)-1,3,4-thiadiazol-2-yl 1763 5-(3-Br-C6H4)-1,3,4-thiadiazol-2-yl 1764 5-(4-Br-C6H4)-1,3,4-thiadiazol-2-yl 1765 5-(2-F-C6H4)-1,3,4-thiadiazol-2-yl 25 1766 5-(3-F-C6H4)-1,3,4-thiAAi~zol-2-yl 1767 5-(4-F-C6H4)-1,3,4-thiadiazol-2-yl 1768 5-(2,4-Cl2-C6H3)-1,3,4-thi A~i ~zol-2-yl 1769 5-(2~5-Cl2-C6H3)-1~3~4-thi A~ i A 7.ol-2-yl 30 1770 5-(2,6-Cl2-C6H3)-1,3,4-thiadiazol-2-yl 1771 5-(3,4-C12-C6H3)-1,3,4-thiadiazol-2-yl 1772 5-(2,4-F2-C6H3)-1,3,4-thi~iAZol-2-yl 1773 5-(2,5-F2-C6H3)-1,3,4-thiadiazol-2-yl 1774 5-(2,6-F2-C6H3)-1,3,4-thia~iA7ol-2-yl 35 1775 5-(3,4-F2-C6H3)-1,3,4-thiadiazol-2-yl 1776 5-(2-Cl, 5-OCH3-C6H3)-1,3,4-thiadiazol-2-yl 1777 5-(2-Cl, 5-CH3-C6H3)-1,3,4-thiadiazol-2-yl 1778 5-(5-Cl, 2-OCH3-C6H3)-1,3,4-thiadiazol-2-yl 40 1779 5-(5-Cl, 2-CH3-C6H3)-1,3,4-thiadiazol-2-yl 1780 5-[2,5-(CH3)2-C6H3l-1,3,4-thiadiazol-2-yl 1781 1-CH(CH3)2-imidazol-4-yl 1782 1-C(CH3)3-imidazol-4-yl 1783 1-cyclopropylimidazol-4-yl 45 1784 1-C6H5-imidazol-4-yl 1785 1-(2-CH3-C6H4)imidazol-4-yl No. R4 1786 1-(3-CH3-C6H4)imidazol-4-yl 1787 1-~4-CH3-C6H4)imidazol-4-yl 1788 1-(3-OCH3-C6H4)imidazol-4-yl 1789 1-(4-OCH3-C6H4)imidazol-4-yl 1790 1-(4-N02-C6H4)imidazol-4-yl 1791 1-(3-N02-C6H4)imidazol-4-yl 10 1792 1-(4-CN-C6H4)imidazol-4-yl 1793 1-(3-CN-C6H4)imidazol-4-yl 1794 1-(3-CF3-C6H4)imidazol-4-yl 1795 1-(4-CF3-C6H4)imidazol-4-yl 1796 1-(4-C(CH3)3C6H4)imidazol-4-yl 1797 1-(2-Cl-C6H4)imidazol-4-yl 1798 1-(3-Cl-C6H4)imidazol-4-yl 1799 1-(4-Cl-C6H4)imidazol-4-yl 1800 1-(2-Br-C6H4)imidazol-4-yl 20 1801 1-(3-Br-C6H4)imidazol-4-yl 1802 1-(4-~r-C6H4)imidazol-4-yl 1803 1-(2-F-C6H4)imidazol-4-yl 1804 1-(3-F-C6H4)imidazol-4-yl 1805 1-(4-F-C6H4)imidazol-4-yl 1806 1-(2,4-C12-C6H3)imidazol-4-yl 1807 1-(2,5-C12-C6H3)imidazol-4-yl 1808 1-(2,6-C12-C6H3)imidazol-4-yl 1809 1-(3,4-C12-C6H3)imidazol-4-yl 30 1810 1-(2,4-F2-C6H3)imidazol-4-yl 1811 1-(2,5-F2-C6H3)imidazol-4-yl 1812 1-(2,6-F2-C6H3)imidazol-4-yl 1813 1-(3,4-F2-C6H3)imidazol-4-yl 1814 1-(2-Cl, 5-OCH3-C6H3)imidazol-4-yl 35 1815 1-(2-Cl, 5-CH3-C6H3)imidazol-4-yl 1816 1-(5-Cl, 2-OCH3-C6H3)imidazol-4-yl 1817 1-(5-Cl, 2-CH3-C6H3)imidazol-4-yl 1818 1-[2,5-(CH3)2-C6H3]imidazol-4-yl The compounds IIIa are novel R3~
C = N - OH IIIa I

R4' the variables having the following meanings:

R3' is hydrogen, alkyl, haloalkyl or cycloalkyl R4' is hydrogen or unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl;

20 R5' is alkylsulfonyl or unsubstituted or substituted alkyl, alkenyl, alkynyl or cycloalkyl.

Synthesis is carried out according to the processes described on pp. 3/4, or [lacuna] can be prepared in analogy to processes 25 known per se.

The compounds VIIa R3n C = S VIIa RSnO - N ~
I

are also novel, the variables having the following meanings:

R3" is alkyl, haloalkyl or cycloalkyl;
R4" is unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl;

R5" is alkylsulfonyl or unsubstituted or substituted alkyl, alkenyl, alkynyl or cycloalkyl and it not being possible for R3 , R4 and R5 simultaneously to be methyl Synthesis is carried out in analogy to known processes (cf. Acta 5 Cienc. Indica. Chem 11, 124 (1985); J. Org. Chem. 51, 5198 (1986); J. Org. Chem. 52, 2927 (1987); Tetrahedron Lett. 24, 1851 (1983).) Also novel are the compounds XII, XIII, XIV, XI [sic], XVI and C = N- O - CH2~ ~ (R2)m (XII) R50 - N ~ C=O

C=N - O - CH2~(R2 )m (XIII) RsO - N / C=O

R4 Hal (Hal = halogen) R3 ~ (R2)m (XIV) C= ~ O--CH2 R50 - N / C=O

C= N--O--CH 2 J3 ( R2 ) m ( XV ) 5R50--N / C=0 C= N--O--CH2/¢~ ( R2 ) m ( XVI ) 15R50--N ~ C=0 R4 C=0 N ( Z ) _R

(Z = H or Cl-C4-alkyl) C=N--O--CH2/~3 (R2 )m ( XVII ) C=O

Y-Rl 35 the variables in each case having the same meaning as the corresponding radicals of compounds of the formula I. The synthesis of these compounds is described on pages 2 to 10 of this application.

40 The compounds I are suitable as fungicides.

The compounds I are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the class of Ascomycetes and Basidiomycetes. They are 45 systemically active in some cases and can be employed as foliar and soil fungicides.

CA 0223l66l l998-04-07 They are of particular importance for the control of a multiplicity of fungi on various crop plants such as wheat, rye, barley, oats, rice, corn, grass, cotton, soybeans, coffee, sugar cane, grapes, fruit and decorative plants and vegetable plants 5 such as cucumbers, beans and cucurbits, and on the seeds of these plants.

They are specifically suitable for the control of the following plant diseases: Erysiphe gr~ ;n;s (powdery mildew) in cereals, 10 Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia species on cereals, Rhizoctonia species on cotton, rice and grass, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, 15 Septoria nodorum on wheat, Botrytis cinerea (gray mold) on strawberries, vines, vegetables and decorative plants, Cercospora arachidicola on groundnuts, Pseudocercosporella herpotrichoides on wheat, barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusarium and Verticillium 20 species on various plants, Plasmopara viticola on vines, Pseudoperonospora species in hops and cucumbers, Alternaria species on vegetables and fruit.

The compounds I are applied by treating the fungi or the plants, 25 seeds, materials or the soil to be protected from fungal attack with a fungicidally effective amount of the active compounds.
They are applied before or after the infection of the materials, plants or seeds by the fungi.

30 Using formulation auxiliaries known per se, they can be converted into the customary formulations (compositions), such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application form depends on the particular intended use; in each case it should guarantee a fine and uniform 35 distribution of the compounds I. The formulations are prepared in a known manner, eg. by extending the active compound with solvents and/or carriers, if desired using emulsifiers and dispersants, it being possible in the case of water as a diluent also to use other organic solvents as auxiliary solvents.
40 Suitable auxiliaries for this purpose are essentially: solvents such as aromatics (eg. xylene), chlorinated aromatics (eg.
chlorobenzenes), paraffins (eg. petroleum fractions), alcohols (eg. methanol, butanol), ketones (eg. cyclohexanone), amines ~eg.
ethanolamine, dimethylformamide) and water; carriers such as 45 ground natural minerals (eg. kaolins, argillaceous earths, talc, chalk) and ground synthetic minerals (eg. highly disperse silica, silicates); emulsifiers such as nonionic and anionic emulsifi¢rs (eg. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin-sulfite waste liquors and methylcellulose.

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

Depending on the type of effect desired, the application rates are from 0.01 to 2.0 kg of active compound per ha.
In seed treatment, amounts of active compound of from 0.001 to 0.1 g, preferably 0.01 to 0.05 g, per kilogram of seed are in general needed.

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

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

The following list of fungicides with which the compounds according to the invention can be applied together is inten~e~ to 25 illustrate the combination possibilities, but not restrict them:

sulfur, dithiocarbamates and their derivatives, such as ferric dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, 30 manganese zinc ethylene~i~minebisdithiocarbamate~ tetramethyl-thiuram disulfides [sic], ammonia complex of zinc N,N-ethylene-bisdithiocarbamate, ammonia complex of zinc N,N'-propylenebisdi-thiocarbamate, zinc N,N'-propylenebisdithiocarbamate, N,N'-poly-propylenebis(thiocarbamoyl) disulfide;
nitro derivatives, such as dinitro(l-methylheptyl)phenyl croto-nate, 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl isopropyl carbonate, diisopropyl 5-nitroisophthalate;
heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethyl phthalimidophosphonothioate, 5-amino-1-[bis(dimethylamino)phos-phinyl]-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthra-45 quinone, 2-thio-1,3-dithiolo[4,5-b]quinoxaline, methyl l-(butyl-carbamoyl)-2-benzimidazolecarbamate, 2-methoxycarbonylamino-benzimidazole, 2-(fur-2-yl)benzimidazole, 2-(thiazol-4-yl)benz-CA 0223l66l l998-04-07 imidazole, N - ( 1, 1, 2, 2 - tetrachloroethylthio)tetrahydrophthalimide, N - trichloromethylthiotetrahydrophthalimide, N-trichloromethyl-thiophthalimide;

5 N-dichlorofluoromethylthio- N', N'-dimethyl-N-phenylsulfamide, 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole, 2-thiocyanato-methylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, pyridine-2-thio-1-oxide [sic], 8-hydroxyquinoline or its copper salt, 10 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methyl-furan-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide, 2,4,5-trimethylfuran-3-carboxanilide, N-cyclohexyl-2,5-dimethyl-15 furan-3-carbox~ e~ N-cyclohexyl-N-methoxy-2,5-dimethyl-furan-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, 2,2,2-trichloro-1-(4-morpholinyl)ethylformamide, piperazine-1,4-diylbis(l-(2,2,2-trichloroethyl)formamide lsic], 1-(3,4-di-chloroanilino)-l-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-20 N-tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclododecyl-morpholine or its salts, N-[3-(p-tert-butylphenyl)-2-methyl-propyl]-cis-2,6-dimethylmorpholine, N-[3-(p-tert-butylphenyl)-2-methylpropyl]piperidine~ 1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-lH-1,2,4-triazole, 1-[2-(2,4-dichloro-25 phenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-lH-1,2,4-triazole, N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)- N ' - imidazolylurea, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(lH-1,2,4-triazol-1-yl)-2-butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(lH-1,2,4-tria-zol-l-yl)-2-butanol, a-(2-chlorophenyl)-a-(4-chlorophenyl)-30 5-pyrimidinemethanol, 5-butyl-2-dimethylamino-4-hydroxy-6-methyl-pyrimidine, bis(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene, 1,2-bis(3-methoxy-carbonyl-2-thioureido)benzene;

35 and various fungicides, such as dodecylguanidine acetate, 3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]glutarimide, hexachlorobenzene, DL-methyl- N - ( 2,6-dimethylphenyl)- N - 2 - furoyl alaninate, DL- N - ( 2,6-dimethylphenyl)-N-(2'-methoxyacetyl)alanine methyl ester, N - ( 2,6-dimethylphenyl)- N - chloroacetyl-D,L-2-amino-40 butyrolactone, DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)alanine methyl ester, 5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine, 3-[3,5-dichlorophenyl(-5-methyl-5-methoxymethyl]-1,3-oxazolidine-2,4-dione [sic], 3-(3,5-di-chlorophenyl)-l-isopropylcarbamoylhydantoin, N - ( 3,5-dichloro-45 phenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano-[ N - ethylaminocarbonyl-2-methoximino]acetamide, 1-[2-(2,4-di-chlorophenyl)pentyl]-lH-1,2,4-triazole, 2, 4-difluoro-U U3~

a-(lH-1,2,4-triazolyl-1-methyl)benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-~hloro-2-aminopyridine, 1-((bis(4-fluorophenyl)methylsilyl)methyl)-lH-1,2,4-triazole;

strobilurins such as methyl E-methoximino[a-(o-tolyl-oxy)-o-tolyl]acetate, methyl E-2-{2-[6-(2-cyanophenoxy)pyrimi-din-4-yloxy]phenyl}-3-methoxyacrylate, methyl E-methoximino-[a-(2-phenoxyphenyl)]acetamide, methyl E-methoximino-[a-(2,5-di-10 methylphenoxy)-o-tolyl]acetamide;

anilinopyrimidines such as N-(4,6-dimethylpyrimidin-2-yl)aniline, N-[4-methyl-6-(1-propynyl)pyrimidin-2-yl]aniline, N-(4-methyl-6-cyclopropylpyrimidin-2-yl)aniline;
phenylpyrroles such as 4-(2,2-difluoro-1,3-benzodioxol-4-yl)-pyrrole-3-carbonitrile;

cinn~m~-des such as 3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-20 acrylic acid morpholide, (2RS,3SR)-1-[3-(2-chlorophenyl)-2-[4-fluorophenyl)oxiran-2-ylmethyl]-lH-1,2,4-triazole.

The compounds of the formula I are additionally suitable for controlling pests of the insects, arachnids and nematodes 25 classes. They can be employed as pesticides in crop protection and in the hygiene, stored material protection and veterinary sectors.

The harmful insects include: from the order of the butterflies 30 (Lepidoptera), for example, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia ! conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia 35 pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula 40 undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia 45 clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera 5 littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni, Zeiraphera canadensis;

from the order of the beetles (Coleoptera), for example, Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus 10 solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema 15 tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera posti~a, Ips typographus, Lema bilineata, Lema melanopus, 20 Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus [sic] sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., 25 Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus, Sitophilus granaria;

from the order of the dipterans (Diptera), for example, Aedes 30 aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipen~is, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus 35 intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina [sicl, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, 40 Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea, Tipula paludosa;

CA 0223l66l l998-04-07 from the order of the thrips (Thysanoptera), for example, Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci;

from the order of the hymenopterans (Hymenoptera), for example, Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta;
from the order of the bugs (Heteroptera), for example, Acroster-num hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus 15 lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor;

from the order of the plant-sucking insects (Homoptera), for example, Acyrthosiphon ono~rychis, Adelges laricis, Aphidula 20 nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nordmann;An~e, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, 25 Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, 30 Trialeurodes vaporariorum, Viteus vitifolii;

from the order of the termites (Isoptera), for example, Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus, Termes natalensis;
from the order of the orthopterans (Orthoptera), for example, Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migrato-ria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus 40 mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus, Tachycines asynamorus;

45 from the order of the Arachnoidea, for example, spiders (Acarina) such as Amblyomma americanum, Amblyomma variegatum, Argas persi-cus, Boophilus annulatus, Boophilus decoloratus, Boophilus micro-plus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor sil-varum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma trun-catum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Paratetranychus pilosus, Dermanyssus gallinae, 5 Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sar-coptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius, Tetranychus urticae;

10 from the class of the nematodes, for example, root gall nematodes, eg. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, eg. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stem and leaf nematodes, eg.
15 Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, 20 Pratylenchus goodeyi.

The compounds I can be applied as such, in the form of their formulations (compositions) obtained using formulation auxiliaries known per se or the application forms prepared 25 therefrom, eg. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dust compositions, scattering compositions or granules, by spraying, atomizing, dusting, scattering or watering. The application forms depend entirely on the intended uses; in each 30 case they should if possible guarantee the finest dispersion of the active compounds according to the invention.

The active compound concentrations in the ready-to-use preparations can be varied within relatively wide ranges.
In general, they are from 0.0001 to 10%, preferably from 0.01 to 1% .

The active compounds can also be used with good effect in the 40 ultra-low volume method (ULV), it being possible to apply formulations containing more than 95% by weight of active compound or even the active compound without additives.

Under outdoor conditions, the application rate of active compound 45 for controlling pests is from 0.1 to 2.0, preferably 0.2 to 1.0 kg/ha.

For the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions, mineral oil fractions of medium to high boiling point are suitable, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or ~nim~l origin, 5 aliphatic, cyclic and aromatic hydrocarbons, eg. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar 10 solvents, eg. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water.

Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (oil dispersions) by 15 addition of water. To prepare emulsions, pastes or oil dispersions, the substances can be homogenized in water as such or dissolved in an oil or solvent, by means of wetting agents, adherents, dispersants or emulsifiers. However, concentrates consisting of active substance, wetting agent, adherent, 20 dispersant or emulsifier and possibly solvent or oil can also be prepared which are suitable for dilution with water.

Suitable surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphtha-25 lenesulfonic acid, phenolsulfonic acid and dibutylnaphthalene-sulfonic acid, alkylarylsulfonates, alkylsulfates, alkyl-sulfonates, fatty alcohol sulfates and fatty acids and also their alkali metal and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ethers, condensation products of sulfonated 30 naphthalene and naphthalene derivatives with formaldehyde, con-densation products of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol [sic]
ether, ethoxylated isooctylphenol, octylphenol or nonylphenol, alkylphenol [sic] or tributylphenyl polyglycol ether, alkylaryl 35 polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors or methylcellulose.
Powder, scattering and dusting compositions can be prepared by mixing or joint grinding of the active substances with a solid carrier.

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

Examples of formulations are:

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

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

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

IV. 20 parts by weight of a compound I according to the invention are dissolved in a mixture which consists of 60 parts by weight of cycloheY~none, 30 parts by weight of isobutanol, 5 parts by weight of the addition product of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 5 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil (active compound content 16% by weight).

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

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

VII. 20 parts by weight of a compound I according to the invention are dissolved in a mixture which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition product of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil. By pouring the solution into and finely dispersing it in 100,000 parts by weight of water, an aqueous dispersion is obtained which contains 0.02% by weight of the active compound.

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

Granules, eg. coated, impregnated and homogeneous granules, can be prepared by binding the active compounds to solid carriers.
30 Solid carriers are, for example, mineral earths, such as silica gel, silicic acids, silica gels [sic], silicates, talc, kaolin, attapulgous clay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as 35 eg. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as grain flour, tree bark, wood and nutshell meal, cellulose powder and other solid carriers.

Oils of various types, herbicides, fungicides, other pesticides 40 and bactericides can be added to the active compounds, if desired only immediately before application (tank mix). These agents can be admixed with the agents according to the invention in a weight ratio from 1:10 to 10:1.

CA 0223l66l l998-04-07 Synthesis Example The chemical shift (in ppm) of the 1H-NMR spectra was measured against tetramethylsilane: br = broad; s = singlet, m =
5 multiplet.

Preparation of (E,E)-2-methoxyimino-2-[2'-[(1"-methyl-l~-N-methoxy-N-methylamino)iminooxymethyl]phenyl]acetic acid N-methylamide ~ ~ N J ~

I / N ~I ~ \ N / \
O

6.3 [lacuna] (61 mmol~ of N-methoxy-N-methylacetamide were initially introduced into 100 ml of xylene, treated with 24.7 g (61 mmol) of 2,4-bis(4-methoxyphenyl~ 3-dithia-2~4-diphos-20 phetane-2,4-disulfide (Lawesson's reagent) and stirred at 100~C
for 1 hour. The reaction product was purified by column chromatography. 5.9 g of N-methoxy-N-methylthioacetamide were obtained as an orange oil.

25 1H-NMR (CDCl3): 2.63 (s, 3H); 3.7 (s, 3H); 3.8 (s, 3H).

1.9 g (23 mmol) of sodium acetate and 5.4 g (23 mmol) of E-2-methoximino-2-[(2'-aminooxymethyl)phenyl]acetic acid monomethylamide (cf. also EP-A 585 751) were added to a solution 30 of 2.7 g (23 mmol) of N-methoxy-N-methylthioacetamide in 50 ml of ethanol and the reaction mixture was stirred at 70~C for 16 hours and concentrated. The product was purified by column chromatography on silica gel (methyl tert-butyl ether/n-h~Ane).
1.9 g of the title compound were obt~;ne~ as a colorless oil.
H-NMR (CDCl3): 1.94 (s, 3H); 2.81 (s, 3H); 2.87 (d, 3H); 3.57 (s, 3H); 3.92 (s, 3H); 4.85 (s, 2H); 6.69 (s, br, lH); 7.14-7.43 (m, 4H).

Use Examples 1. Example of the action against harmful fungi 5 It was possible to show the fungicidal action of the compounds of the formula I by the following tests:

The active compounds were prepared as a 20% strength emulsion in a mixture of 70% by weight of cyclohe~none, 20% by weight of 10 Nekanil~ LN ~Lutensol~ AP6, wetting agent having emulsifier and dispersant action based on ethoxylated alkylphenols) and 10% by weight of Emulphor~ EL (Emulan~ EL, emulsifier based on ethoxylated fatty alcohols) and diluted with water according to the concentration desired. Assessment was carried out visually.
Activity against wheat mildew Leaves of wheat seedlings of the variety Fruhgold grown in pots were sprayed with aqueous spray mixture and dusted with oidia 20 (spores) of wheat mildew (Erysiphe graminis var. tritici) 24 hours after the spray coating had dried on. The test plants were then placed in a greenhouse at from 20 to 22~C and 75 to 80%
relative atomspheric humidity. After 7 days, the extent of mildew development was determined.
The compound according to the invention, the comparison agent A
disclosed in WO-A 93/16986 (Table 1, No. H-2) and the comparison agent B disclosed in WO-A 94/14761 (Table 8, No. 1) were employed according to the methods described above.

~N N ~ Co.. lpli~onagentA

Comparison agentB
~\ S ~ N/ \~ (WO-A 94114761, Table 8, No. 1) ~ / NH ~ ~ / O

, 0050~46271 % attack on the leaves after application of an aqueous active compound preparation containing 63 ppm of active compound Active compound 0 5 according to synthesis example Comparison agent A 60 Comparison agent B 40 Untreated 70 The results of the abovementioned tests clearly show the advantages of the compound according to the invention.

2. Examples of the action against animal pests It was possible to show the action of the compounds of the general formula I against animal pests by the following tests The active compounds were prepared a) as a 0.1% strength solution in acetone or b) as a 10% strength emulsion in a mixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil~ LN (Lutensol~ AP6, wetting agent having emulsifing and dispersant action based on ethoxylated alkyl phenols) and 10% by weight of Emulphor~
EL ~Emulan~ EL, emulsifier based on ethoxylated fatty alcohols) and diluted with acetone in the case of a) or with water in the 30 case of b) according to the concentration desired.

After conclusion of the tests, the lowest concentration in each case was determined at which the compounds still produced an 80 - 100% inhibition or mortality in comparison with the 35 untreated control tests (activity threshold or minimum concentration).

Claims (17)

We claim:
1. An oxyaminooxime ether of the formula I

where the variables have the following meanings:

X is NOCH3, CHOCH3 or CHCH3;
Y is O or NZ, Z being hydrogen or C1-C4-alkyl;
R1 is hydrogen or C1-C4-alkyl;
R2 is cyano, nitro, halogen, C1-C4-alkyl, trifluoromethyl or C1-C4-alkoxy;
m is 0, 1 or 2, it being possible for the radicals R2 to be different if m is 2;
R3 is hydrogen, alkyl, haloalkyl or cycloalkyl;
R4 is hydrogen or unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl;
R5 is hydrogen, alkylsulfonyl or unsubstituted or substituted alkyl, alkenyl, alkynyl or cycloalkyl, or its salts.
2. A process for preparing compounds of the formula I as claimed in claim 1, which comprises reacting a benzyl derivative of the formula II

where L1 is a nucleophilically replaceable leaving group, with an oxime of the formula III

3. A process for preparing compounds of the formula I as claimed in claim 1, which comprises reacting a benzyl derivative of the formula II as claimed in claim 2 with a hydroxyaminohy-droxyimine of the formula IV

to give a compound of the formula V

and then reacting V with a compound of the formula VI
R5-L3 (VI) where L3 is a nucleophilically replaceable leaving group, to give I.
4. A process for preparing compounds of the formula I as claimed in claim 1, which comprises reacting a benzylhydroxylamine of the formula IIa with a thioamide of the formula VII

5. A process for preparing compounds of the formula I as claimed in claim l, which comprises reacting a hydroximic acid derivative of the formula X

where L4 is a displaceable group, with a hydroxylamine of the formula VIII

AMENDED SHEET
6. A composition suitable for controlling animal pests or harmful fungi, comprising a compound of the formula I or one of its salts as claimed in claim 1 and at least one formulation auxiliary.
7. A composition as claimed in claim 6 for controlling animal pests of the insects, arachnids or nematodes class.
8. A method of controlling animal pests or harmful fungi, which comprises treating the pests or harmful fungi, their habitat or the plants, surfaces, materials or spaces to be kept free from them with an effective amount of a compound of the formula I or one of its salts as claimed in claim 1.
9. A method for preparing compositions against animal pests or against harmful fungi, which comprises mixing an amount of at least one compound of the formula I, or one of its salts, active against animal pests or against harmful fungi, as claimed in claim 1, and at least one inert liquid and/or solid carrier, and, if desired, at least one surface-active substance.
10. The use of the compounds I as claimed in claim 1 for controlling animal pests or harmful fungi.
11. A compound of the formula IIIa where the variables have the following meanings:

R3' is hydrogen, alkyl, haloalkyl or cycloalkyl;

R4' is hydrogen or unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl;

R5' is alkylsulfonyl or unsubstituted or substituted alkyl, alkenyl, alkynyl or cycloalkyl.
12. A compound of the formula XII

where the variables have the meanings indicated in claim 1.
13. A compound of the formula XIII

Hal = halogen, where the other variables have the meanings indicated in claim 1.
14. A compound of the formula XIV

where the variables have the meanings indicated in claim 1.
15. A compound of the formula XV

where the variables have the meanings indicated in claim 1.
16. A compound of the formula XVI

Z = H or C1-C4-alkyl, where the other variables have the meanings indicated in claim 1.
17. The use of the compounds as claimed in claims 11 to 18 [sic]
as intermediates.
CA002231661A 1995-10-10 1996-09-30 Oxyaminooxime ethers, preparation thereof and intermediates therefor and compositions comprising them for controlling harmful fungi and animal pests Abandoned CA2231661A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19537750A DE19537750A1 (en) 1995-10-10 1995-10-10 Oxiamino oxime ethers, processes and intermediates for their preparation and compositions containing them for combating harmful fungi and animal pests
DE19537750.8 1995-10-10
PCT/EP1996/004255 WO1997013747A1 (en) 1995-10-10 1996-09-30 Oxyamino oxime ethers, methods and intermediate products for their production, and agents containing them and used for controlling harmful fungi and pests

Publications (1)

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AT (1) ATE203514T1 (en)
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HUP9901227A2 (en) 1999-07-28
GR3036534T3 (en) 2001-12-31
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IL123666A0 (en) 1998-10-30

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