4-HALOALKYL-3-HETEROCYCLYLPYRIDINES, 4-HALOALKYL-5-HETEROCYCLYL-PYRIMIDINES AND 4-TRIFLUOROMETHYL-3-OXADIAZOLYLPYRIDINES, PROCESSES FOR THEIR PREPARATION, COMPOSITIONS COMPRISING THEM, AND THEIR USE AS PESTICIDES

Abstract

The present invention relates to 4-Haloalkyl-3-heterocyclylpyridines, 4-haloalkyl-5-heterocyclyl-pyrimidines and 4-trifluoromethyl-3-oxadiazolylpyridines, Processes for Their Preparation, Compositions Comprising Them, and Their Use as PesticidesMore particularly, the present invention relates to 4-trifluoromethyl-3-oxadiazolylpyridines of the formula (I′), to processes for their preparation, to compositions comprising them and to the use of these compounds for controlling animal pests, in particular insects, spider mites, ectoparasites and helminths: wherein X, Y are as defined in the description.

Description

FIELD OF THE INVENTION

The present invention relates to 4-haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclylpyrimidines, to processes for their preparation, to compositions comprising them and to the use of novel and known 4-haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclylpyrimidines for controlling animal pests, in particular insects, spider mites, ectoparasites and helminths. More particularly, the invention relates to 4-trifluoromethyl-3-oxadiazolylpyridines, to processes for their preparation, to compositions comprising them and to their use for controlling animal pests, in particular insects, spider mites, ectoparasites and helminths.

BACKGROUND OF THE INVENTION

It is already known that appropriately substituted pyridines or pyrimidines have acaricidal and insecticidal activity. Thus, WO 95/07891 describes pyridines which carry a cycloalkyl radical in position 4 which is linked via a hetero atom and a group of various substituents in position 3. WO 93/19050 discloses 4-cycloalkylamino- and 4-cycloalkoxypyrimidines which carry in position 5 inter alia alkyl, alkoxy or haloalkoxy groups. However, the desired activity against the harmful organisms is not always sufficient. Additionally, these compounds often have undesirable toxicologic properties toward mammals and aquatic living beings.

Pyridyl-1,2,4-thiadiazoles having fungicidal properties are described in DE-A 42 39 727. The compounds disclosed therein carry the thiadiazole ring in position 2, 3 or 4 of the unsubstituted pyridine.

WO-A-98/57969, which is not prepublished, proposes 4-haloalkylpyridines and -pyrimidines for use as pesticides.

EP-A 0 371 925 discloses some 1,3,4-oxadiazolyl- and 1,3,4-thiadiazolyl-pyrimidines having nematicidal and fungicidal properties. In the biologically effective compounds disclosed in this publication, the pyrimidine carries the oxadiazolyl or thiadiazolyl ring either

a) in position 5 and is optionally substituted by a thiomethyl group in position 2, or

b) in position 2 and is optionally substituted in position 4 and 6, in each case by a methyl group.

Aryltriazole derivatives for use as pesticides are known from EP-A 0 185 256. In addition to the phenyltriazoles, which are particularly preferred, three haloalkyl-3-pyridyltriazoles are disclosed:

3-(2-chlorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole

3-(2,6-difluorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole and

3-(2-chloro-4-fluorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole,

their desired activity at low application rates, however, is not always satisfactory, especially when controlling insects and spider mites.

Some commercially available 4-haloalkyl-3-heterocyclylpyridines are known from the Maybridge Catalogue 1996/1997, Maybridge Chemical CO. LTD., Trevillett Tintagel, GB:

3-(3,5-dichlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(4-trifluoromethyl-3-pyridyl)-3-phenyl-1,2,4-oxadiazole

3-(4-trifluoromethyl-3-pyridyl)-5-phenyl-1,2,4-oxadiazole

5-(2-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(3-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(4-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(2-fluorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(4-fluorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(2,4-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(3,4-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(3,5-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(2,6-dichloro-4-pyridyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(3,5-bistrifluoromethylphenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

2-(2-chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole

2-(3-chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole

2-(4-chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole

2-(2-trifluoromethoxyphenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole

2-(4-trifluoromethoxyphenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole

2-(4-trifluoromethyl-3-pyridyl)-5-phenyl-1,3,4-oxadiazole

2-(4-trifluoromethyl-3-pyridyl)-4-methylthiazolecarbohydrazide

ethyl 2-(4-trifluoromethyl-3-pyridyl)-4-methylthiazolecarboxylate

N-(4-chlorophenyl)carbonyl-N′-[2-(4-trifluoromethyl-3-pyridyl)-4-methyl-5-thiazolyl]carbonylhydrazine

2-(4-trifluoromethyl-3-pyridyl)-4-thiazolecarbohydrazide

4-(4-chlorophenyl)-2-(4-trifluoromethyl-3-pyridyl)thiazole

4-(4-cyanophenyl)-2-(4-trifluoromethyl-3-pyridyl)thiazole

N-(4-trifluoromethylphenyl)carbonyl-N′-[2-(4-trifluoromethyl-3-pyridyl)-4-thiazolyl]carbonylhydrazine

2-(2-(4-trifluoromethyl-3-pyridyl)thiazolyl)-5-chloro-3-methylbenzo[b]thiophene

2-(4-chlorophenylmethylthio)-5-(4-trifluoromethyl-3-pyridyl)-1-methyl-1H-1,3,4-triazole

2-(4-chlorophenylcarbonylmethylthio)-5-(4-trifluoromethyl-3-pyridyl)-1-methyl-1H-1,3,4-triazole and

2-ethoxycarbonylmethylthio-5-(4-trifluoromethyl-3-pyridyl)-1-methyl-1H-1,3,4-triazole.

However, a biological activity toward harmful organisms has hitherto not been disclosed.

SUMMARY OF THE INVENTION

It is an object of the present invention to provide compounds having good insecticidal and acaricidal properties and simultaneously low toxicity toward mammals and aquatic living beings.

DETAILED DESCRIPTION OF THE INVENTION

It has now been found that compounds of the formula I, optionally as salts, have a wider activity spectrum against animal pests and simultaneously more favorable toxicologic properties toward mammals and aquatic living beings than the prior art compounds.

In the formula (I):

Y is halo-C 1 -C 6 -alkyl;

X is CH or N;

m is 0 or 1;

Q is a 5-membered heterocyclic group

in which

	a)	X 1 = W,	X 2 = NR a ,	X 3 = CR b R 1	or
	b)	X 1 = NR a ,	X 2 = CR b R 1 ,	X 3 = W	or
	c)	X 1 = V,	X 2 = CR a R 1 ,	X 3 = NR b	or
	d)	X 1 = V,	X 2 = CR a R 2 ,	X 3 = CR b R 3	or
	e)	X 1 = V,	X 2 = CR 4 R 5 ,	X 3 = CR 6 R 7	or
	f)	X 1 = NR a ,	X 2 = CR b R 1 ,	X 3 = NR 8 ;

R a and R b together are a bond

V is oxygen, sulfur or NR 9 ;

W is oxygen or sulfur;

R 1 is hydrogen,

(C 1 -C 20 )-alkyl, (C 2 -C 20 )-alkenyl, (C 2 -C 20 )-alkynyl, (C 3 -C 8 )-cycloalkyl,

(C 4 -C 8 )-cycloalkenyl, (C 6 -C 8 )-cycloalkynyl,

where the six last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, —C(═W)R 10 , —C(═NOR 10 )R 10 , —C(═NNR 10 2 )R 10 , —C(═W)OR 10 , —C(═W)NR 10 2 , —OC(═W)R 10 , —OC(═W)OR 10 , —NR 10 C(═W)R 10 , —N[C(═W)R 10 ] 2 , —NR 10 C(═W)OR 10 , —C(═W)NR 10 —NR 10 2 , —C(═W)NR 10 —NR 10 [C(═W)R 10 ], —NR 10 —C(═W)NR 10 2 , —NR 10 —NR 10 C(═W)R 10 , —NR 10 —N[C(═W)R 10 ] 2 , —N[(C═W)R 10 ]—NR 10 2 , —NR 10 —NR 10 [(C═W)R 10 ], —NR 10 —NR 10 [(C═W)WR 10 ], —NR 10 —R 10 [(C═W)NR 10 2 ], —NR 10 (C═NR 10 )R 10 , —NR 10 (C═NR 10 )NR 10 2 , —O—NR 10 2 , —O—NR 10 (C═W)R 10 , —SO 2 NR 10 2 , —NR 10 SO 2 R 10 , —SO 2 OR 10 , —OSO 2 R 10 , —OR 10 , —NR 10 2 , —SR 10 , —SiR 10 3 , —SeR 10 , —PR 10 2 , —P(═W)R 10 2 , —SOR 10 , —SO 2 R 10 , —PW 2 R 10 2 , —PW 3 R 10 2 , aryl and heterocyclyl,

the two last-mentioned radicals optionally being substituted by one or more radicals from the group

(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 8 )-cycloalkyl, (C 4 -C 8 )-cycloalkenyl, (C 6 -C 8 )-cycloalkynyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-haloalkynyl, halogen, —OR 10 , —NR 10 2 , —SR 10 , —SiR 10 3 , —C(═W)R 10 , —C(═W)OR 10 , —C(═W)NR 10 2 , —SOR 10 , —SO 2 R 10 , nitro, cyano and hydroxyl,

aryl,

which is optionally substituted by one or more radicals from the group

(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 8 )-cycloalkyl, (C 4 -C 8 )-cycloalkenyl and (C 6 -C 8 )-cycloalkynyl,

where these six abovementioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, —C(═W)R 10 , —C(═W)OR 10 , —C(═W)NR 10 2 , —OR 10 , —NR 10 2 , —SR 10 , —SOR 10 and —SO 2 R 10 ,

halogen, cyano, nitro, —C(═W)R 10 , —C(═NOR 10 )R 10 , —C(═NNR 10 2 )R 10 , —C(═W)OR 10 , —C(═W)NR 10 2 , —OC(═W)R 10 , —OC(═W)OR 10 , —NR 10 C(═W)R 10 , —N[C(═W)R 10 ] 2 , —NR 10 C(═W)OR 10 , —OR 10 , —NR 10 2 , —SR 10 , —SiR 10 3 , —PR 10 2 , —SOR 10 , —SO 2 R 10 , —PW 2 R 10 2 and —PW 3 R 10 2 ,

heterocyclyl,

which is optionally substituted by one or more radicals from the group

(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 8 )-cycloalkyl, (C 4 -C 8 )-cycloalkenyl and (C 6 -C 8 )-cycloalkynyl,

where the six abovementioned radicals are optionally substituted by one or more radicals from the group

cyano, nitro, halogen, —C(═W)R 10 , —C(═W)OR 10 , —C(═W)NR 10 2 , —NR 10 C(═W)R 10 , —N[C(═W)R 10 ] 2 , —OC(═W)R 10 , —OC(═W)OR 10 , —OR 10 , —NR 10 2 , —SR 10 , —SOR 10 and —SO 2 R 10 ;

halogen, cyano, nitro, —C(═W)R 10 , —C(═W)OR 10 , —C(═W)NR 10 2 , —OC(═W)R 10 , —OR 10 , —NR 10 2 , —SR 10 , —SOR 10 and —SO 2 R 10 ;

—OR 10 , —NR 10 2 , —SR 10 , —SOR 10 , —SO 2 R 10 , —C(═W)R 10 , —C(═NOR 10 )R 10 , —C(═NNR 10 2 )R 10 , —C(═W)OR 10 , —C(═W)NR 10 2 , —OC(═W)R 10 , —OC(═W)OR 10 , —NR 10 C(═W)R 10 , —N[C(═W)R 10 ] 2 , —NR 10 C(═W)OR 10 , —C(═W)NR 10 —NR 10 2 , —C(═W)NR 10 —NR 10 [C(═W)R 10 ], —NR 10 —C(═W)NR 10 2 , —NR 10 —NR 10 C(═W)R 10 , —NR 10 —NC(═W)R 10 2 , —N(C═W)R 10 —NR 10 2 , —NR 10 —NR 10 [(C═W)R 10 ], —NR 10 —NR 10 [(C═W)WR 10 ], —NR 10 —NR 10 [(C═W)NR 10 2 ], —NR 10 (C═NR 10 )R 10 , —NR 10 (C═NR 10 )NR 10 2 , —O—NR 10 2 , —O—NR 10 (C═W)R 10 , —SO 2 NR 10 2 , —NR 10 SO 2 R 10 , —SO 2 OR 10 , —OSO 2 R 10 , —SC(═W)R 10 , —SC(═W)OR 10 , —SC(═W)R 10 , —PR 10 2 , —PW 2 R 10 2 , —PW 3 R 10 2 , SiR 10 3 or halogen;

R 2 and R 3 independently of one another have the definitions given in R 1 ;

R 2 and R 3 together form a 5- to 7-membered ring which may be partially or fully unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, the oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R 1 ;

R 4 and R 6 independently of one another have the definitions given in R 1 ;

R 4 and R 6 together form a 4- to 7-membered ring which may be partially or fully unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, the oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R 1 ;

R 5 and R 7 independently of one another are hydrogen,

(C 1 -C 20 )-alkyl, (C 2 -C 20 )-alkenyl, (C 2 -C 20 )-alkynyl, (C 3 -C 8 )-cycloalkyl, (C 4 -C 8 )-cycloalkenyl, (C 6 -C 8 )-cycloalkynyl,

where the six last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, —C(═W)R 10 , —C(═NOR 10 )R 10 , —C(═NNR 10 2 )R 10 , —C(═W)OR 10 , —C(═W)NR 10 2 , —OC(═W)R 10 , —OC(═W)OR 10 , —NR 10 C(═W)R 10 , —N[C(═W)R 10 ] 2 , —NR 10 C(═W)OR 10 , —C(═W)NR 10 —NR 10 2 , —C(═W)NR 10 —NR 10 [C(═W)R 10 ], —NR 10 —C(═W)NR 10 2 , —NR 10 —NR 10 C(═W)R 10 , —NR 10 —N[C(═W)R 10 ] 2 , —N[(C═W)R 10 ]—NR 10 2 , —NR 10 —NR 10 [(C═W)R 10 ], —NR 10 —NR 10 [(C═W)WR 10 ], —NR 10 —NR 10 [(C═W)NR 10 2 ], —NR 10 (C═NR 10 )R 10 , —NR 10 (C═NR 10 )NR 10 2 , —O—NR 10 2 , —O—NR 10 (C═W)R 10 , —OR 10 , —NR 10 2 , —SR 10 , —SiR 10 3 , —SeR 10 , —PR 10 2 , —P(═W)R 10 2 , —SOR 10 , —SO 2 R 10 , —PW 2 R 10 2 , —PW 3 R 10 2 , aryl and heterocyclyl,

of which the two mentioned last are optionally substituted by one or more radicals from the group

(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 8 )-cycloalkyl, (C 4 -C 8 )-cycloalkenyl, (C 6 -C 8 )-cycloalkynyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-haloalkynyl, halogen, —OR 10 , —NR 10 2 , —SR 10 , —SiR 10 3 , —C(═W)R 10 , —C(═W)OR 10 , —C(═W)NR 10 2 , —SOR 10 , —SO 2 R 10 , nitro, cyano and hydroxyl,

aryl,

which is optionally substituted by one or more radicals from the group

(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 8 )-cycloalkyl, (C 4 -C 8 )-cycloalkenyl and (C 6 -C 8 )-cycloalkynyl,

where these six abovementioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, —C(═W)R 10 , —C(═W)OR 10 , —C(═W)NR 10 2 , —OR 10 , —NR 10 2 , —SR 10 , —SOR 10 and —SO 2 R 10 ;

halogen, cyano, nitro, —C(═W)R 10 , —C(═NOR 10 )R 10 , —C(═NNR 10 2 )R 10 , —C(═W)OR 10 , —C(═W)NR 10 2 , —OC(═W)R 10 , —OC(═W)OR 10 , —NR 10 C(═W)R 10 , —N[C(═W)R 10 ] 2 , —NR 10 C(═W)OR 10 , —OR 10 , —NR 10 2 , —SR 10 , —SiR 10 3 , —PR 10 2 , —SOR 10 , —SO 2 R 10 , —PW 2 R 10 2 and —PW 3 R 10 2 ;

pyridyl,

which is optionally substituted by one or more radicals from the group

(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 8 )-cycloalkyl, (C 4 -C 8 )-cycloalkenyl and (C 6 -C 8 )-cycloalkynyl,

where the six abovementioned radicals are optionally substituted by one or more radicals from the group

cyano, nitro, halogen, —C(═W)R 10 , —C(═W)OR 10 , —C(═W)NR 10 2 , —OR 10 , —NR 10 2 , —SR 10 , —SOR 10 and —SO 2 R 10 ,

halogen, cyano, nitro, —C(═W)R 10 , —C(═W)OR 10 , —C(═W)NR 10 2 , —OC(═W)R 10 , —OR 10 , —NR 10 2 , —SR 10 , —SOR 10 and —SO 2 R 10 ;

—C(═W)R 10 , —C(═NOR 10 )R 10 , —C(═NNR 10 2 )R 10 , —C(═W)OR 10 , —C(═W)NR 10 2 or halogen;

R 4 and R 5 together form a 4- to 7-membered ring which may be partially unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R 1 ;

R 4 and R 5 together form one of the groups ═O, ═S or ═N—R 9 ;

R 6 and R 7 together form a 5- to 7-membered ring which may be partially unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R 1 ;

R 6 and R 7 together form one of the groups ═O, ═S or ═N—R 9 ;

R 8 is hydrogen,

(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 8 )-cycloalkyl, (C 4 -C 8 )-cycloalkenyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkyl, (C 3 -C 8 )-cycloalkyl-(C 2 -C 4 )-alkenyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkenyl, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkyl, (C 2 -C 6 )-alkenyl-(C 3 -C 8 )-cycloalkyl, (C 2 -C 6 )-alkynyl-(C 3 -C 8 )-cycloalkyl, (C 1 -C 6 )-alkyl-(C 4 -C 8 )-cycloalkenyl, (C 2 -C 6 )-alkenyl-(C 4 -C 8 )-cycloalkenyl,

where the fourteen last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkenyloxy, (C 2 -C 6 )-alkynyloxy, (C 1 -C 6 )-haloalkyloxy, (C 2 -C 6 )-haloalkenyloxy, (C 2 -C 6 )-haloalkynyloxy, (C 3 -C 8 )-cycloalkoxy, (C 4 -C 8 )-cycloalkenyloxy, (C 3 -C 8 )-halocycloalkoxy, (C 4 -C 8 )-halocycloalkenyloxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkoxy, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkoxy, (C 3 -C 8 )-cycloalkyl-(C 2 -C 4 )-alkenyloxy, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkenyloxy, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkoxy, (C 2 -C 6 )-alkenyl-(C 3 -C 8 )-cycloalkoxy, (C 2 -C 6 )-alkynyl-(C 3 -C 8 )-cycloalkoxy, (C 1 -C 6 )-alkyl-(C 4 -C 8 )-cycloalkenyloxy, (C 2 -C 6 )-alkenyl-(C 4 -C 8 )-cycloalkenyloxy, (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkoxy, (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkenyloxy, carbamoyl, (C 1 -C 6 )-mono- or dialkylcarbamoyl, (C 1 -C 6 )-mono- or dihaloalkylcarbamoyl, (C 3 -C 8 )-mono- or dicycloalkylcarbamoyl, (C 1 -C 6 )-alkoxycarbonyl, (C 3 -C 8 )-cycloalkoxycarbonyl, (C 1 -C 6 )-alkanoyloxy, (C 3 -C 8 )-cycloalkanoyloxy, (C 1 -C 6 )-haloalkoxycarbonyl, (C 1 -C 6 )-haloalkanoyloxy, (C 1 -C 6 )-alkaneamido, (C 1 -C 6 )-haloalkaneamido, (C 2 -C 6 )-alkeneamido, (C 3 -C 8 )-cycloalkaneamido, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkaneamido, (C 1 -C 6 )-alkylthio, (C 2 -C 6 )-alkenylthio, (C 2 -C 6 )-alkynylthio, (C 1 -C 6 )-haloalkylthio, (C 2 -C 6 )-haloalkenylthio, (C 2 -C 6 )-haloalkynylthio, (C 3 -C 8 )-cycloalkylthio, (C 4 -C 8 )-cycloalkenylthio, (C 3 -C 8 )-halocycloalkylthio, (C 4 -C 8 )-halocycloalkenylthio, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkylthio, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkylthio, (C 3 -C 8 )-cycloalkyl-(C 2 -C 4 )-alkenylthio, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkenylthio, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkylthio, (C 2 -C 6 )-alkenyl-(C 3 -C 8 )-cycloalkylthio, (C 2 -C 6 )-alkynyl-(C 3 -C 8 )-cycloalkylthio, (C 1 -C 6 )-alkyl-(C 4 -C 8 )-cycloalkenylthio, (C 2 -C 6 )-alkenyl-(C 4 -C 8 )-cycloalkenylthio, (C 1 -C 6 )-alkylsulfinyl, (C 2 -C 6 )-alkenylsulfinyl, (C 2 -C 6 )-alkynylsulfinyl, (C 1 -C 6 )-haloalkylsulfinyl, (C 2 -C 6 )-haloalkenylsulfinyl, (C 2 -C 6 )-haloalkynylsulfinyl, (C 3 -C 8 )-cycloalkylsulfinyl, (C 4 -C 8 )-cycloalkenylsulfinyl, (C 3 -C 8 )-halocycloalksulfinyl, (C 4 -C 8 )-halocycloalkenylsulfinyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkylsulfinyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkylsulfinyl, (C 3 -C 8 )-cycloalkyl-(C 2 -C 4 )-alkenylsulfinyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkenylsulfinyl, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkylsulfinyl, (C 2 -C 6 )-alkenyl-(C 3 -C 8 )-cycloalkylsulfinyl, (C 2 -C 6 )-alkynyl-(C 3 -C 8 )-cycloalkylsulfinyl, (C 1 -C 6 )-alkyl-(C 4 -C 8 )-cycloalkenylsulfinyl, (C 2 -C 6 )-alkenyl-(C 4 -C 8 )-cycloalkenylsulfinyl, (C 1 -C 6 )-alkylsulfonyl, (C 2 -C 6 )-alkenylsulfonyl, (C 2 -C 6 )-alkynylsulfonyl, (C 1 -C 6 )-haloalkylsulfonyl, (C 2 -C 6 )-haloalkenylsulfonyl, (C 2 -C 6 )-haloalkynylsulfonyl, (C 3 -C 8 )-cycloalkylsulfonyl, (C 4 -C 8 )-cycloalkenylsulfonyl, (C 3 -C 8 )-halocycloalkylsulfonyl, (C 4 -C 8 )-halocycloalkenylsulfonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkylsulfonyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkylsulfonyl, (C 3 -C 8 )-cycloalkyl-(C 2 -C 4 )-alkenylsulfonyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkenylsulfonyl, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkylsulfonyl, (C 2 -C 6 )-alkenyl-(C 3 -C 8 )-cycloalkylsulfonyl, (C 2 -C 6 )-alkynyl-(C 3 -C 8 )-cycloalkylsulfonyl, (C 1 -C 6 )-alkyl-(C 4 -C 8 )-cycloalkenylsulfonyl, (C 2 -C 6 )-alkenyl-(C 4 -C 8 )-cycloalkenylsulfonyl, (C 1 -C 6 )-alkylamino, (C 2 -C 6 )-alkenylamino, (C 2 -C 6 )-alkynylamino, (C 1 -C 6 )-haloalkylamino, (C 2 -C 6 )-haloalkenylamino, (C 2 -C 6 )-haloalkynylamino, (C 3 -C 8 )-cycloalkylamino, (C 4 -C 8 )-cycloalkenylamino, (C 3 -C 8 )-halocycloalkamino, (C 4 -C 8 )-halocycloalkenylamino, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkylamino, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkylamino, (C 3 -C 8 )-cycloalkyl-(C 2 -C 4 )-alkenylamino, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkenylamino, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkylamino, (C 2 -C 6 )-alkenyl-(C 3 -C 8 )-cycloalkylamino, (C 2 -C 6 )-alkynyl-(C 3 -C 8 )-cycloalkylamino, (C 1 -C 6 )-alkyl-(C 4 -C 8 )-cycloalkenylamino, (C 2 -C 6 )-alkenyl-(C 4 -C 8 )-cycloalkenylamino, (C 1 -C 6 )-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, arylcarbamoyl, aroyl, aroyloxy, aryloxycarbonyl, aryl-(C 1 -C 4 )-alkoxy, aryl-(C 2 -C 4 )-alkenyloxy, aryl-(C 1 -C 4 )-alkylthio, aryl-(C 2 -C 4 )-alkenylthio, aryl-(C 1 -C 4 )-alkylamino, aryl-(C 2 -C 4 )-alkenylamino, aryl-(C 1 -C 6 )-dialkylsilyl, diaryl-(C 1 -C 6 )-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl,

of which the nineteen last-mentioned radicals are optionally substituted in their cyclic moiety by one or more substituents from the group

halogen, cyano, nitro, amino, hydroxyl, thio, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-haloalkylthio, (C 1 -C 4 )-alkylamino, (C 1 -C 4 )-haloalkylamino, formyl and (C 1 -C 4 )-alkanoyl;

aryl, which is optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkenyloxy, (C 2 -C 6 )-alkynyloxy, (C 1 -C 6 )-haloalkyloxy, (C 2 -C 6 )-haloalkenyloxy, (C 2 -C 6 )-haloalkynyloxy, (C 3 -C 8 )-cycloalkoxy, (C 4 -C 8 )-cycloalkenyloxy, (C 3 -C 8 )-halocycloalkoxy, (C 4 -C 8 )-halocycloalkenyloxy, carbamoyl, (C 1 -C 6 )-mono- or dialkylcarbamoyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkanoyloxy, (C 1 -C 6 )-mono- or dihaloalkylcarbamoyl, (C 1 -C 6 )-haloalkoxycarbonyl, (C 1 -C 6 )-haloalkanoyloxy, (C 1 -C 6 )-alkaneamido, (C 1 -C 6 )-haloalkaneamido, (C 2 -C 6 )-alkeneamido, (C 1 -C 6 )-alkylthio, (C 2 -C 6 )-alkenylthio, (C 2 -C 6 )-alkynylthio, (C 1 -C 6 )-haloalkylthio, (C 2 -C 6 )-haloalkenylthio, (C 2 -C 6 )-haloalkynylthio, (C 3 -C 8 )-cycloalkylthio, (C 4 -C 8 )-cycloalkenylthio, (C 3 -C 8 )-halocycloalkthio, (C 3 -C 8 )-halocycloalkenylthio, (C 1 -C 6 )-alkylsulfinyl, (C 2 -C 6 )-alkenylsulfinyl, (C 2 -C 6 )-alkynylsulfinyl, (C 1 -C 6 )-haloalkylsulfinyl, (C 2 -C 6 )-haloalkenylsulfinyl, (C 2 -C 6 )-haloalkynylsulfinyl, (C 3 -C 8 )-cycloalkylsulfinyl, (C 4 -C 8 )-cycloalkenylsulfinyl, (C 3 -C 8 )-halocycloalksulfinyl, (C 4 -C 8 )-halocycloalkenylsulfinyl, (C 1 -C 6 )-alkylsulfonyl, (C 2 -C 6 )-alkenylsulfonyl, (C 2 -C 6 )-alkynylsulfonyl, (C 1 -C 6 )-haloalkylsulfonyl, (C 2 -C 6 )-haloalkenylsulfonyl, (C 2 -C 6 )-haloalkynylsulfonyl, (C 3 -C 8 )-cycloalkylsulfonyl, (C 4 -C 8 )-cycloalkenylsulfonyl, (C 3 -C 8 )-halocycloalksulfonyl, (C 4 -C 8 )-halocycloalkenylsulfonyl, (C 1 -C 6 )-alkylamino, (C 2 -C 6 )-alkenylamino, (C 2 -C 6 )-alkynylamino, (C 1 -C 6 )-haloalkylamino, (C 2 -C 6 )-haloalkenylamino, (C 2 -C 6 )-haloalkynylamino, (C 3 -C 8 )-cycloalkylamino, (C 4 -C 8 )-cycloalkenylamino, (C 3 -C 8 )-halocycloalkamino and (C 4 -C 8 )-halocycloalkenylamino,

—C(═W)R 11 , OR 11 or NR 11 2 ;

R 9 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 8 )-cycloalkyl, (C 4 -C 8 )-cycloalkenyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkyl, (C 3 -C 8 )-cycloalkyl-(C 2 -C 4 )-alkenyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkenyl,

where the nine last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, (C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkenyloxy, (C 2 -C 6 ) alkynyloxy and (C 1 -C 6 )-haloalkyloxy;

R 10 is hydrogen,

(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 8 )-cycloalkyl, (C 4 -C 8 )-cycloalkenyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkyl, (C 3 -C 8 )-cycloalkyl-(C 2 -C 4 )-alkenyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkenyl, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkyl, (C 2 -C 6 )-alkenyl-(C 3 -C 8 )-cycloalkyl, (C 2 -C 6 )-alkynyl-(C 3 -C 8 )-cycloalkyl, (C 1 -C 6 )-alkyl-(C 4 -C 8 )-cycloalkenyl, (C 2 -C 6 )-alkenyl-(C 4 -C 8 )-cycloalkenyl,

where the fourteen last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkenyloxy, (C 2 -C 6 )-alkynyloxy, (C 1 -C 6 )-haloalkyloxy, (C 2 -C 6 )-haloalkenyloxy, (C 2 -C 6 )-haloalkynyloxy, (C 3 -C 8 )-cycloalkoxy, (C 4 -C 8 )-cycloalkenyloxy, (C 3 -C 8 )-halocycloalkoxy, (C 4 -C 8 )-halocycloalkenyloxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkoxy, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkoxy, (C 3 -C 8 )-cycloalkyl-(C 2 -C 4 )-alkenyloxy, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkenyloxy, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkoxy, (C 2 -C 6 )-alkenyl-(C 3 -C 8 )-cycloalkoxy, (C 2 -C 6 )-alkynyl-(C 3 -C 8 )-cycloalkoxy, (C 1 -C 6 )-alkyl-(C 4 -C 8 )-cycloalkenyloxy, (C 2 -C 6 )-alkenyl-(C 4 -C 8 )-cycloalkenyloxy, (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkoxy, (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkenyloxy, carbamoyl,

(C 1 -C 6 )-mono- or dialkylcarbamoyl, (C 1 -C 6 )-mono- or dihaloalkylcarbamoyl, (C 3 -C 8 )-mono- or dicycloalkylcarbamoyl, (C 1 -C 6 )-alkoxycarbonyl, (C 3 -C 8 )-cycloalkoxycarbonyl, (C 1 -C 6 )-alkanoyloxy, (C 3 -C 8 )-cycloalkanoyloxy, (C 1 -C 6 )-haloalkoxycarbonyl, (C 1 -C 6 )-haloalkanoyloxy, (C 1 -C 6 )-alkaneamido, (C 1 -C 6 )-haloalkaneamido, (C 2 -C 6 )-alkeneamido, (C 3 -C 8 )-cycloalkaneamido, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkaneamido, (C 1 -C 6 )-alkylthio, (C 2 -C 6 )-alkenylthio, (C 2 -C 6 )-alkynylthio, (C 1 -C 6 )-haloalkylthio, (C 2 -C 6 )-haloalkenylthio, (C 2 -C 6 )-haloalkynylthio, (C 3 -C 8 )-cycloalkylthio, (C 4 -C 8 )-cycloalkenylthio, (C 3 -C 8 )-halocycloalkthio, (C 4 -C 8 )-halocycloalkenylthio, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkylthio, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkylthio, (C 3 -C 8 )-cycloalkyl-(C 2 -C 4 )-alkenylthio, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkenylthio, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkylthio, (C 2 -C 6 )-alkenyl-(C 3 -C 8 )-cycloalkylthio, (C 2 -C 6 )-alkynyl-(C 3 -C 8 )-cycloalkylthio, (C 1 -C 6 )-alkyl-(C 4 -C 8 )-cycloalkenylthio, (C 2 -C 6 )-alkenyl-(C 4 -C 8 )-cycloalkenylthio, (C 1 -C 6 )-alkylsulfinyl, (C 2 -C 6 )-alkenylsulfinyl, (C 2 -C 6 )-alkynylsulfinyl, (C 1 -C 6 )-haloalkylsulfinyl, (C 2 -C 6 )-haloalkenylsulfinyl, (C 2 -C 6 )-haloalkynylsulfinyl, (C 3 -C 8 )-cycloalkylsulfinyl, (C 4 -C 8 )-cycloalkenylsulfinyl, (C 3 -C 8 )-halocycloalksulfinyl, (C 4 -C 8 )-halocycloalkenylsulfinyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkylsulfinyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkylsulfinyl, (C 3 -C 8 )-cycloalkyl-(C 2 -C 4 )-alkenylsulfinyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkenylsulfinyl, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkylsulfinyl, (C 2 -C 6 )-alkenyl-(C 3 -C 8 )-cycloalkylsulfinyl, (C 2 -C 6 )-alkynyl-(C 3 -C 8 )-cycloalkylsulfinyl, (C 1 -C 6 )-alkyl-(C 4 -C 8 )-cycloalkenylsulfinyl, (C 2 -C 6 )-alkenyl-(C 4 -C 8 )-cycloalkenylsulfinyl, (C 1 -C 6 )-alkylsulfonyl, (C 2 -C 6 )-alkenylsulfonyl, (C 2 -C 6 )-alkynylsulfonyl, (C 1 -C 6 )-haloalkylsulfonyl, (C 2 -C 6 )-haloalkenylsulfonyl, (C 2 -C 6 )-haloalkynylsulfonyl, (C 3 -C 8 )-cycloalkylsulfonyl, (C 4 -C 8 )-cycloalkenylsulfonyl, (C 3 -C 8 )-halocycloalksulfonyl, (C 4 -C 8 )-halocycloalkenylsulfonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkylsulfonyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkylsulfonyl, (C 3 -C 8 )-cycloalkyl-(C 2 -C 4 )-alkenylsulfonyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkenylsulfonyl, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkylsulfonyl, (C 2 -C 6 )-alkenyl-(C 3 -C 8 )-cycloalkylsulfonyl, (C 2 -C 6 )-alkynyl-(C 3 -C 8 )-cycloalkylsulfonyl, (C 1 -C 6 )-alkyl-(C 4 -C 8 )-cycloalkenylsulfonyl, (C 2 -C 6 )-alkenyl-(C 4 -C 8 )-cycloalkenylsulfonyl, (C 1 -C 6 )-alkylamino, (C 2 -C 6 )-alkenylamino, (C 2 -C 6 )-alkynylamino, (C 1 -C 6 )-haloalkylamino, (C 2 -C 6 )-haloalkenylamino, (C 2 -C 6 )-haloalkynylamino, (C 3 -C 8 )-cycloalkylamino, (C 4 -C 8 )-cycloalkenylamino, (C 3 -C 8 )-halocycloalkamino, (C 4 -C 8 )-halocycloalkenylamino, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkylamino, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkylamino, (C 3 -C 8 )-cycloalkyl-(C 2 -C 4 )-alkenylamino, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkenylamino, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkylamino, (C 2 -C 6 )-alkynyl-(C 3 -C 8 )-cycloalkylamino, (C 1 -C 6 )-alkyl-(C 4 -C 8 )-cycloalkenylamino, (C 2 -C 6 )-alkenyl-(C 4 -C 8 )-cycloalkenylamino, (C 1 -C 6 )-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, aryl-(C 1 -C 4 )-alkoxy, aryl-(C 2 -C 4 )-alkenyloxy, aryl-(C 1 -C 4 )-alkylthio, aryl-(C 2 -C 4 )-alkenylthio, aryl-(C 1 -C 4 )-alkylamino, aryl-(C 2 -C 4 )-alkenylamino, aryl-(C 1 -C 6 )-dialkylsilyl, diaryl-(C 1 -C 6 )-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl,

where the cyclic moiety of the fourteen last-mentioned radicals is optionally substituted by one or more radicals from the group

halogen, cyano, nitro, amino, hydroxyl, thio, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 3 -C 8 )-cycloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-haloalkylthio, (C 1 -C 4 )-alkylamino, (C 1 -C 4 )-haloalkylamino, formyl and (C 1 -C 4 )-alkanoyl;

aryl, 5- or 6-membered heteroaromatic,

where the two last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkenyloxy, (C 2 -C 6 )-alkynyloxy, (C 1 -C 6 )-haloalkyloxy, (C 2 -C 6 )-haloalkenyloxy, (C 2 -C 6 )-haloalkynyloxy, (C 3 -C 8 )-cycloalkoxy, (C 4 -C 8 )-cycloalkenyloxy, (C 3 -C 8 )-halocycloalkoxy, (C 4 -C 8 )-halocycloalkenyloxy, carbamoyl, (C 1 -C 6 )-mono- or dialkylcarbamoyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkanoyloxy, (C 1 -C 6 )-mono- or dihaloalkylcarbamoyl, (C 1 -C 6 )-haloalkoxycarbonyl, (C 1 -C 6 )-haloalkanoyloxy, (C 1 -C 6 )-alkaneamido, (C 1 -C 6 )-haloalkaneamido, (C 2 -C 6 )-alkeneamido, (C 1 -C 6 )-alkylthio, (C 2 -C 6 )-alkenylthio, (C 2 -C 6 )-alkynylthio, (C 1 -C 6 )-haloalkylthio, (C 2 -C 6 )-haloalkenylthio, (C 2 -C 6 )-haloalkynylthio, (C 3 -C 8 )-cycloalkylthio, (C 4 -C 8 )-cycloalkenylthio, (C 3 -C 8 )-halocycloalkthio, (C 4 -C 8 )-halocycloalkenylthio, (C 1 -C 6 )-alkylsulfinyl, (C 2 -C 6 )-alkenylsulfinyl, (C 2 -C 6 )-alkynylsulfinyl, (C 1 -C 6 )-haloalkylsulfnyl, (C 2 -C 6 )-haloalkenylsulfinyl, (C 2 -C 6 )-haloalkynylsulfinyl, (C 3 -C 8 )-cycloalkylsulfinyl, (C 4 -C 8 )-cycloalkenylsulfinyl, (C 3 -C 8 )-halocycloalksulfinyl, (C 4 -C 8 )-halocycloalkenylsulfinyl, (C 1 -C 6 )-alkylsulfonyl, (C 2 -C 6 )-alkenylsulfonyl, (C 2 -C 6 )-alkynylsulfonyl, (C 1 -C 6 )-haloalkylsulfonyl, (C 2 -C 6 )-haloalkenylsulfonyl, (C 2 -C 6 )-haloalkynylsulfonyl, (C 3 -C 8 )-cycloalkylsulfonyl, (C 4 -C 8 )-cycloalkenylsulfonyl, (C 3 -C 8 )-halocycloalksulfonyl, (C 4 -C 8 )-halocycloalkenylsulfonyl, (C 1 -C 6 )-alkylamino, (C 2 -C 6 )-alkenylamino, (C 2 -C 6 )-alkynylamino, (C 1 -C 6 )-haloalkylamino, (C 2 -C 6 )-haloalkenylamino, (C 2 -C 6 )-haloalkynylamino, (C 3 -C 8 )-cycloalkylamino, (C 4 -C 8 )-cycloalkenylamino, (C 3 -C 8 )-halocycloalkylamino and (C 4 -C 8 )-halocycloalkenylamino;

R 11 is (C 1 -C 10 )-alkyl, haloalkyl, aryl,

which is optionally substituted by one or more radicals from the group

halogen, cyano, nitro, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkyl, amino, (C 1 -C 4 )-monoalkylamino and (C 1 -C 4 )-dialkylamino;

NR 10 2 , OR 10 or SR 10 .

The term “halogen” includes fluorine, chlorine, bromine and iodine.

The term “(C 1 -C 4 )-alkyl” is to be understood as a straight-chain or branched hydrocarbon radical having 1, 2, 3 or 4 carbon atoms, such as, for example, the methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radical. Correspondingly, alkyl radicals having a greater range of carbon atoms are to be understood as straight-chain or branched saturated hydrocarbon radicals which contain a number of carbon atoms which corresponds to the range stated. Thus, the term “(C 1 -C 6 )-alkyl” includes the abovementioned alkyl radicals, and, for example, the pentyl, 2-methylbutyl, 1,1-dimethylpropyl, hexyl radical. The term “(C 1 -C 10 )-alkyl” is to be understood as the abovementioned alkyl radicals, and, for example, the nonyl, 1-decyl or 2-decyl radical and the term “(C 1 -C 20 )-alkyl” is to be understood as the abovementioned alkyl radicals, and, for example, the undecyl, dodecyl, pentadecyl or eicosyl radical.

“(C 1 -C 4 )-Haloalkyl” is to be understood as an alkyl group mentioned under the term “(C 1 -C 4 )-alkyl” in which one or more hydrogen atoms are replaced by the same number of identical or different halogen atoms, preferably by fluorine or chlorine, such as the trifluoromethyl, the 1-fluoroethyl, the 2,2,2-trifluoroethyl, the chloromethyl, fluoromethyl, the difluoromethyl and the 1,1,2,2-tetrafluoroethyl group.

“(C 1 -C 4 )-Alkoxy” is to be understood as an alkoxy group whose hydrocarbon radical has the meaning given under the term “(C 1 -C 4 )-alkyl”. Alkoxy groups embracing a greater range of carbon atoms are to be understood correspondingly.

The terms “alkenyl” and “alkynyl” having a prefix stating the range of carbon atoms denote a straight-chain or branched hydrocarbon radical having a number of carbon atoms corresponding to the range stated which comprises at least one multiple bond which may be in any position of the unsaturated radical in question. “(C 2 -C 4 )-Alkenyl” is thus, for example, the vinyl, allyl, 2-methyl-2-propene or 2-butenyl group; “(C 2 -C 6 )-alkenyl” denotes the abovementioned radicals and, for example, the pentenyl, 2-methylpentenyl or the hexenyl group. The term “(C 2 -C 20 )-alkenyl” is to be understood as the abovementioned radicals and, for example, the 2-decenyl or the 2-eicosenyl group. “(C 2 -C 4 )-Alkynyl” is, for example, the ethynyl, propargyl, 2-methyl-2-propyne or 2-butynyl group. “(C 2 -C 6 )-Alkynyl” is to be understood as the abovementioned radicals and, for example, the 2-pentynyl- or the 2-hexynyl group and “(C 2 -C 20 )-alkynyl” is to be understood as the abovementioned radicals and, for example, the 2-octynyl or the 2-decynyl group.

“(C 3 -C 8 )-Cycloalkyl” denotes monocyclic alkyl radicals, such as the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radical and bicyclic alkyl radicals, such as the norbornyl radical.

The term “(C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkyl” is to be understood as, for example, the cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylbutyl radical, and the term “(C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkyl is to be understood as, for example, the 1-methylcyclopropyl, 1-methylcyclopentyl, 1-methylcyclohexyl, 3-hexylcyclobutyl and 4-tert-butyl-cyclohexyl radical.

“(C 1 -C 4 )-Alkoxy-(C 1 -C 6 )-alkyloxy” is an alkoxy group as defined above which is substituted by a further alkoxy group, such as, for example, 1-ethoxyethoxy.

“(C 3 -C 8 )-Cycloalkoxy” or “(C 3 -C 8 )-cycloalkylthio” is to be understood as one of the abovementioned (C 3 -C 8 )-cycloalkyl radicals which is linked via an oxygen or sulfur atom.

“(C 3 -C 8 )-Cycloalkyl-(C 1 -C 6 )-alkoxy” is, for example, the cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclohexylethoxy or the cyclohexylbutoxy group;

The term “(C 1 -C 4 )-alkyl-(C 3 -C 8 )-cycloalkoxy” is, for example, the methylcyclopropyloxy, methylcyclobutyloxy or the butylcyclohexyloxy group.

“(C 1 -C 6 )-Alkylthio” is an alkylthio group whose hydrocarbon radical has the meaning given under the term “(C 1 -C 6 )-alkyl”.

Correspondingly, “(C 1 -C 6 )-alkylsulfinyl” is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfinyl group and “(C 1 -C 6 )-alkylsulfonyl” is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfonyl group.

“(C 1 -C 6 )-Alkylamino” is a nitrogen atom which is substituted by one or two identical or different alkyl radicals of the above definition.

The term “(C 1 -C 6 )-mono- or dialkylcarbamoyl” is a carbamoyl group having one or two hydrocarbon radicals which have the meaning given under the term “(C 1 -C 6 -alkyl)” and which, in the case of two hydrocarbon radicals, may be identical or different.

Correspondingly, “(C 1 -C 6 )-dihaloalkylcarbamoyl” is a carbamoyl group which carries two (C 1 -C 6 )-haloalkyl radicals in accordance with the above definition or one (C 1 -C 6 )-haloalkyl radical and one (C 1 -C 6 )-alkyl radical in accordance with the above definition.

“(C 1 -C 6 )-Alkanoyl” is, for example, the acetyl, propionyl, butyryl or 2-methylbutyryl group.

The term “aryl” is to be understood as an isocyclic aromatic radical preferably having 6 to 14, in particular 6 to 12, carbon atoms, such as, for example, phenyl, naphthyl or biphenylyl, preferably phenyl. “Aroyl” is thus an aryl radical as defined above which is attached via a carbonyl group, such as, for example, the benzoyl group.

The term “heterocyclyl” denotes a cyclic radical which may be fully saturated, partially unsaturated or fully unsaturated and which may be interrupted by at least one or more identical atoms from the group nitrogen, sulfur or oxygen, oxygen atoms, however, not being directly adjacent to one another and at least one carbon atom being present in the ring, such as, for example, a thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3,4-triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo[b]thiophene, benzo[b]furan, indole, benzo[c]thiophene, benzo[c]furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, pyridine, pyrazine, pyrimidine, pyridazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,4,5-tetrazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine 4H-quinolizine; piperidine, pyrrolidine, oxazoline, tetrahydrofuran, tetrahydropyran, isoxazolidine or thiazolidine radical. The term “heteroaromatic” thus embraces, from among the meanings mentioned above under “heterocyclyl”, in each case the fully unsaturated aromatic heterocyclic compounds.

“Aryl-(C 1 -C 4 )-alkoxy” is an aryl radical which is attached via a (C 1 -C 4 )-alkoxy group, for example the benzyloxy, phenylethoxy, phenylbutoxy or naphthylmethoxy radical.

“Arylthio” is an aryl radical attached via a sulfur atom, for example the phenylthio or the 1- or 2-naphthylthio radical. Correspondingly, “aryloxy” is, for example, the phenoxy or 1- or 2-naphthyloxy radical.

“Aryl-(C 1 -C 4 )-alkylthio” is an aryl radical which is attached via an alkylthio radical, for example the benzylthio, naphthylmethylthio or the phenylethylthio radical.

The term “(C 1 -C 6 )-trialkylsilyl” denotes a silicon atom which carries three identical or different alkyl radicals in accordance with the above definition. Correspondingly “aryl-(C 1 -C 6 )-dialkylsilyl” is a silicon atom which carries one aryl radical and two identical or different radicals in accordance with the above definition, “diaryl-(C 1 -C 6 )-alkylsilyl” is a silicon atom which carries one alkyl radical and two identical or different aryl radicals in accordance with the above definition, and “triarylsilyl” is a silicon atom which carries three identical or different aryl radicals in accordance with the above definition.

In cases where two or more radicals R 10 are present in a substituent, such as, for example, in —C(═W)NR 10 2 , these radicals may be identical or different.

Preference is given to those compounds of the formula I in which

Y is C 1 -C 6 -alkyl which is mono- or polysubstituted by chlorine and/or fluorine;

m is zero;

Q is a 5-membered heterocyclic group

 in which

a) X 2 =NR a and X 3 =CR b R 1 or

b) X 2 =CR a R 2 and X 3 =CR b R 3 or

c) X 2 =CR 4 R 5 and X 3 =CR 6 R 7 ;

R a and R b together are a bond;

R 1 , R 2 , R 3 , R 4 and R 6 are each independently of one another hydrogen, halogen, C 1 -C 12 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, where the four last-mentioned hydrocarbon radicals are optionally mono- or polysubstituted by identical or different radicals from a group A1 consisting of C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkylsulfonylamino, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino, where the eleven first-mentioned radicals of group A1 are each optionally mono- or polysubstituted by identical or different radicals from a group B1 consisting of halogen, cyano, C 1 -C 3 -alkoxy and phenyl which is optionally mono- or polysubstituted by one or more halogen atoms and where the three last-mentioned radicals of group A1 are each optionally mono- or polysubstituted by identical or different radicals from a group B2 consisting of halogen, cyano, nitro, C 1 -C 3 -alkyl and C 1 -C 3 -alkoxy, or are C 1 -C 6 -alkylcarbonyl, C l -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkoxycarbonyl, phenyl, pyridyl, furyl, thienyl, pyrryl, where the eight last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from group B1, or are OR 10 , SR 10 or N(R 10 ) 2 ;

R 5 and R 7 are each independently of one another hydrogen, halogen, C 1 -C 12 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, where the four last-mentioned hydrocarbon radicals are optionally mono- or polysubstituted by identical or different radicals from a group A2 consisting of C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, C 1 -C 6 -alkylcarbonylamino, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino, where the ten first-mentioned radicals of group A2 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A2 are each optionally mono- or polysubstituted by identical or different radicals from the group B2, or are C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkoxycarbonyl, phenyl, pyridyl, furyl, thienyl, pyrryl, where the eight last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from the group B1, or are OR 10 , SR 10 or N(R 10 ) 2 ;

R 10 is hydrogen, benzyl, C 1 -C 6 -alkyl, C 1 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, phenyl, C 1 -C 6 -alkylcarbonyl or C 1 -C 6 -alkylsulfonyl, where the eight last-mentioned radicals are optionally mono- or polysubstituted by identical or different halogen atoms.

Particular preference is given to compounds of the formula I in which

Y is trifluoromethyl;

R 1 , R 2 , R 3 , R 4 and R 6 are each independently of one another halogen, C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A3 consisting of C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkylaminocarbonyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylamino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkylsulfonylamino, phenyl, furyl, pyrryl, thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the eleven first-mentioned radicals of group A3 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A3 are each optionally mono- or polysubstituted by identical or different radicals from the group B2, or are OR 10 , SR 10 or N(R 10 ) 2 ;

R 5 and R 7 are each independently of one another halogen, C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A4 consisting of C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkylaminocarbonyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylamino, C 1 -C 4 -alkylcarbonylamino, phenyl, furyl, pyrryl, thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the ten first-mentioned radicals of group A4 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A4 are each optionally mono- or polysubstituted by identical or different radicals from the group B2, or are OR 10 , SR 10 or N(R 10 ) 2 ;

R 10 is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, phenyl, C 1 -C 4 -alkylcarbonyl or C 1 -C 4 -alkylsulfonyl, where the six last-mentioned radicals are optionally mono- or polysubstituted by identical or different halogen atoms.

Very particular preference is given to compounds of the formula I in which

R 1 , R 2 , R 3 , R 4 and R 6 are each independently of one another C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A5 consisting of C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkylaminocarbonyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylamino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkylsulfonylamino, phenyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the eight first-mentioned radicals of group A5 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A5 are each optionally mono- or polysubstituted by identical or different radicals from the group B2;

R 5 and R 7 are each independently of one another C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A6 consisting of C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkylaminocarbonyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylamino, C 1 -C 4 -alkylcarbonylamino, phenyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the seven first-mentioned radicals of group A6 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A6 are each optionally mono- or polysubstituted by identical or different radicals from the group B2.

Depending on the nature of the substituents defined above, the compounds of the formula (I) have acidic or basic properties and can form salts. If the compounds of the formula (I) carry, for example, groups such as hydroxyl, carboxyl and other groups inducing acidic properties, these compounds can be reacted with bases to give salts. Suitable bases are, for example, hydroxides, carbonates, bicarbonates of the alkali metals and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, further ammonia, primary, secondary and tertiary amines having (C 1 -C 4 )-alkyl radicals and also mono-, di- and trialkanolamines of (C 1 -C 4 )-alkanols. If the compounds of the formula (I) carry, for example, groups such as amino, alkylamino and other groups inducing basic properties, these compounds can be reacted with acids to give salts. Suitable acids are, for example, mineral acids, such as hydrochloric acid, sulfuric acid and phosphoric acid, organic acids, such as acetic acid, oxalic acid and acidic salts, such as NaHSO 4 and KHSO 4 . The salts which can be obtained in this manner likewise have insecticidal, acaricidal and nematicidal properties.

The compounds of the formula (I) may have one or more asymmetric carbon atoms or stereoisomers on double bonds. Enantiomers or diastereomers may therefore be present. The invention embraces both the pure isomers and mixtures thereof. The mixtures of diastereomers can be separated into the isomers by customary methods, for example by selective crystallization from suitable solvents or by chromatography. Racemates can be separated into the enantiomers by customary methods.

The present invention also provides processes for preparing compounds of the formula I:

To prepare compounds of the formula (I) in which

a) X 1 =W, X 2 =NR a , X 3 =CR b R 1

and R a , R b and R 1 are as defined above and W is oxygen, activated derivatives of the acid of the formula (II)

where X and Y are as defined above, are reacted in the presence of a base with a compound of the formula (III)

in which the radical R 1 is as defined in formula (I). Suitable activated derivatives are, for example, acyl halides, esters and anhydrides. Suitable bases are amines, such as triethylamine, diisopropylethylamine, pyridine or lutidine, alkali metal hydroxides, alkali metal alkoxides, such as sodium ethoxide or potassium tert-butoxide, or alkylmetal compounds, such as butyllithium.

Depending on the conditions, the reaction described above can be carried out as a one-step process or as a two-step process via intermediates of the formula (IV):

Compounds of the formula (IV) can be cyclized to the 1,2,4-oxadiazoles by heating in an inert solvent at temperatures of up to 180° C.

Compounds of the formula (IV) are also directly obtainable from the acid of the formula (II) and amidoximes of the formula (III) by using a dehydrating reagent such as dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide or N,N′-carbonyldiimidazole.

Both acids of the formula (II) and amidoximes of the formula (III) are commercially available or can be prepared by methods known from the literature (see, for example: Houben-Weyl, Methoden der organischen Chemie, Volume X/4, pages 209-212; EP-A 0 580 374; G. F. Holland, J. N. Pereira, J. Med. Chem., 1967, 10, 149).

In the abovementioned case a) where W is sulfur, the compounds of the formula (I) can be obtained in a manner known from the literature by reaction of a compound of the formula (VII) with an electrophilic amination reagent, such as hydroxylamine-O-sulfonic acid (Y. Lin, S. A. Lang, S. R. Petty, J. Org. Chem. 1980, 45, 3750).

The compounds of the formula (VII) required as starting materials for this reaction can be prepared by reacting the thioamides of the formula (VIII) with dialkylamide dialkyl acetals, of formula (IX), where R 1 is as defined above and R 12 and R 13 are each C 1 -C 4 -alkyl.

To prepare compounds of the formula (I) in which

b) X 1 =NR a , X 2 =CR b R 1 , X 3 =W

and R a , R b and R 1 are as defined above, and W is oxygen, amidoximes of the formula (V) can be reacted with activated derivatives of the acids of the formula (VI) or with the acids of the formula (VI) themselves.

To prepare compounds of the formula (I) in which

c) X 1 =V, X 2 =CR a R 1 , X 3 =NR b

and R a , R b and R 1 are as defined above and V is sulfur, N,N′-diacylhydrazines of the formula (XIII) can be cyclized with a thiolation reagent, such as Lawesson's reagent (A. A. El-Barbary, S. Scheibyl, S. O. Lawesson, H. Fritz, Acta Chem. Scand. 1980, 597), in an inert solvent, such as toluene.

In the abovementioned case b) where W is oxygen, the compounds of the formula (I) can be prepared by reaction of acids of the formula (II) with hydrazines of the formula (X), in which R 1 is as defined above, using an activating reagent, such as phosphorus oxychloride or phosphorus pentachloride.

It is also possible to react acid hydrazides of the formula (XI) with ortho esters of the formula (XII) where R 1 is as defined above, and R 12 is (C 1 -C 4 )-alkyl.

The reaction can be carried out with or without solvent and with or without an activating reagent. Suitable solvents are hydrocarbons, such as toluene, or ethers, such as 1,2-dimethoxyethane. A suitable activating reagent is, for example, phosphorus oxychloride. The reaction temperature is generally the reflux temperature of the solvent.

To prepare compounds of the formula (I) in which

d) X 1 =V, X 2 =CR a R 2 , X 3 =CR b R 3

and R a , R b and R 3 are as defined above and V is oxygen, compounds of the formula (XIV) are reacted with a dehydrating reagent.

Suitable dehydrating reagents are inorganic acyl chlorides, such as phosphorus oxychloride or thionyl chloride, inorganic acids, such as sulfuric acid or polyphosphoric acid, or a mixture of phosphoric acid and acetic anhydride (Houben-Weyl, Methoden der organischen Chemie, Volume E8a, pages 935-941).

The reaction can be carried out with or without a solvent. Suitable solvents are inert solvents, such as toluene, benzene, dimethoxyethane, dimethylformamide, dimethylacetamide and chlorobenzene. The reaction temperature is advantageously in a range between 50° C. and 150° C.

Compounds of the formula (XIV) can be obtained, for example, by oxidation of the corresponding hydroxyl compound of the formula (XV), it being possible to employ all reagents which are customarily used for this purpose in organic chemistry. (Milos Hudlický, “Oxidations in Organic Chemistry”, ACS Monograph 186, American Chemical Society, Washington, D.C., 1990)

In the abovementioned case d) where V is sulfur, the compounds of the formula (I) can be prepared by condensation of thioamides of the formula (XVII) with carbonyl derivatives of the formula (XVIII), where Z is halogen, in particular chlorine or bromine, acyloxy or sulfonyloxy, in particular methanesulfonyloxy or tolylsulfonyloxy.

To prepare compounds of the formula (I) in which

e) X 1 =V, X 2 =CR 4 R 5 , X 3 =CR 6 R 7

and R 4 , R 5 , R 6 and R 7 are as defined above and V is oxygen, compounds of the formula (XV) are reacted with cyclization reagents, such as Burgess' reagent (G. M. Atkins, E. M. Burgess, J. Am. Chem. Soc. 1968, 90, 4744.), in a solvent such as tetrahydrofuran and 1,4-dioxane, at a temperature which is in a range between room temperature and the reflux temperature of the solvent.

Compounds of the formula (XV) can be obtained by reacting activated derivatives of the acid in formula (II) with β-aminoalcohols of the formula (XVI), if appropriate in the presence of a base, such as, for example, triethylamine, in an inert solvent, such as, for example, dichlormethane.

An acyl halide or an anhydride can be used as activated derivative of the acid.

A number of β-aminoalcohols of the formula (XVI) are commercially available. For others, there is a large number of preparation procedures in the literature, for example a reduction of a-amino acids (B. M. Trost “Comprehensive Organic Synthesis, Reduction”, Volume 8, Pergamon Press, Oxford, 1991).

In the abovementioned case e) where V is sulfur, the compounds of the formula (I) can be prepared by reaction of thioamides of the formula (XVII) with compounds of the formula (XIX), the two substituents Z being as defined above and either identical or different (A. R. Katritzky “Comprehensive Heterocyclic Chemistry”, Volume 6, pages 306-312, Pergamon Press, Oxford).

Thioamides of the formula (XVII) are either commercially available or can be obtained by addition of hydrogen sulfide to the corresponding carbonitriles in the presence of a base (A. E. S. Fairfull, J. L. Lowe, D. A. Peak, J. Chem. Soc. 1952, 742).

For preparing compounds of the formula (I) in which

f) X 1 =NR a , X 2 =CR b R 1 , X 3 =NR 8

and R a , R b , R 1 and R 8 are as defined above, hydrazides of the formula (XX)

are reacted with a compound of the formula (XXI) or with thioamides of the formula (XXII) (Houben-Weyl, Methoden der organischen Chemie, Volume E8d, pages 510-512).

This reaction can be carried out with or without using a solvent, suitable solvents being alcohols, such as ethanol and propanol, or aromatic hydrocarbons, such as toluene and xylene. If the reaction is carried out in a solvent, the reaction temperature to be chosen is advantageously the reflux temperature of the solvent. If, on the other hand, the reaction is carried out without a solvent, it is possible to heat up to 200° C., if appropriate.

Once the group Q has been assembled, for example by condensation, cyclization or cycloaddition reactions, the radicals R 1 to R 9 may be derivatized further, if desired, employing the extensive arsenal of methods of organochemical synthesis.

To assemble compounds of the formula (I), in which m is 1, compounds of the formula (I) in which m is 0 can be treated with an oxidizing agent, such as, for example, meta-chloroperbenzoic acid.

The compounds of the formula (I) (also referred to as “active compounds” hereinbelow) have good plant tolerance, favorable homotherm toxicity and advantageous properties with respect to aquatic organisms and are suitable for controlling animal pests, in particular insects, arachnids (Acarina), helminths and mollusks, especially preferably for controlling insects and arachnids which are encountered in agriculture, in animal husbandry, in forests, in the preservation of stored products and materials and in the hygiene sector. They are active against normally sensitive and resistant species and all or individual stages of development. It has to be emphasized that the control of animal pests may be the result both of a toxic action of the compounds according to the invention and of a deterrant (repellant) action. The abovementioned pests include:

From the order of the Acarina, for example, Acarus siro , Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora , Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa , Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp., and Eutetranychus spp.

From the order of the Isopoda, for example, Oniscus asselus, Armadium vulgar and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea madeirae, Blatella germanica, Acheta domesticus , Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Phylloera vastatrix , Pemphigus spp., Pediculus humanus corporis , Haematopinus spp. and Linognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralis, Thrips tabaci and Frankliniella spp.

From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum , Aphis spp., Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae , Myzus spp., Phorodon humuli, Rhopalosiphum padi , Empoasca spp., Euscelus bilobatus, ephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae , Pseudococcus spp. and Psylla spp.

From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea , Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella , Agrotis spp., Euxoa spp., Feltia spp., Earias insulana , Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura , Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella , Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehnielia, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana , Cuaphalocrocis spp. and Manduca spp.

From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae , Diabrotica spp., Psylloides chrysocephala, Epilachna varivestis , Atomaria spp., Oryzaephilus surinamensis , Anthonumus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrynchus assimilis, Hypera postica , Dermestes spp., Trogoderma, Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus , Ptinus spp., Niptus hololeucus, Gibbium psylloides , Tribolium spp., Tenebrio molitor , Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica and Lissorhoptus spp.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster , Musca spp., Fannia spp., Calliphora erythrocephala , Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit , Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopsis and Ceratophyllus spp. From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans. From the class of helminths, for example, Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis, as well as Fasciola. From the class of Gastropoda, for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp. and Oncomelania spp. From the class of Bivalva, for example, Dreissena spp.

The phytoparasitic nematodes which can be controlled according to the invention include, for example, the root-parasitic soil nematodes, such as, for example, those of the genera Meloidogyne (root gall nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica ), Heterodera and Globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera pallida and Heterodera trifolii ) and of the genera Radopholus (such as Radopholus similis ), Pratylenchus (such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus ), Tylenchulus (such as Tylenchulus semipenetrans ), Tylenchorhynchus (such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni ), Rotylenchus (such as Rotylencus robustus ), Heliocotylenchus (such as Heliocotylenchus multicinctus ), Belonoaimus (such as Belonoaimus longicaudatus ), Longidorus (such as Longidorus elongatus ), Trichodorus (such as Trichodorus primitivus ) and Xiphinema (such as Xiphinema index ).

The nematode genera Ditylenchus (stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor ), Aphelenchoides (leaf nematodes, such as Aphelenchoides ritzemabosi ) and Anguina (blossom nematodes, such as Anguina tritici ) can furthermore be controlled with the compounds according to the invention.

The invention also relates to compositions, in particular insecticidal and acaricidal compositions, which comprise the compounds of the formula (I) in addition to suitable formulation auxiliaries.

The compositions according to the invention in general comprise the active compounds of the formula (I) to the extent of 1 to 95% by weight. They can be formulated in various ways, depending on how this is determined by the biological and/or chemico-physical parameters. Suitable formulation possibilities are therefore: Wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions, sprayable solutions, oil- or water-based dispersions, suspension concentrates (SC), suspoemulsions (SE), dusting powders (DP), seed dressings, granules in the form of microgranules, sprayed granules, absorption granules and adsorption granules, water-dispersible granules (WG), ULV formulations, microcapsules, waxes or baits.

These individual types of formulation are known in principle and are described, for example, in: Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986; van Falkenberg, “Pesticides Formulations”, Marcel Dekker N.Y., 2nd Edition 1972-73; K. Martens, “Spray Drying Handbook”, 3rd Edition 1979, G. Goodwin Ltd. London.

The necessary formulation auxiliaries, i.e. carrier substances and surface-acting substances, such as inert materials, surfactants, solvents and further additives, are likewise known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Edition, Darland Books, Caldwell N.J.; H. v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd Edition, J. Wiley & Sons, N.Y.; Marsden, “Solvents Guide”, 2nd Edition, Interscience, N.Y. 1950; McCutcheon's, “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1967; Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986.

Combinations with other substances having a pesticidal action, fertilizers and/or growth regulators can be prepared on the basis of these formulations, for example in the form of a ready-to-use formulation or as a tank mix. Wettable powders are preparations which are uniformly dispersible in water and which, alongside the active compound, and in addition to a diluent or inert substance, also comprise wetting agents, for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols or alkyl- or alkylphenol-sulfonates, and dispersing agents, for example sodium ligninsulfonate or sodium 2,2′-dinaphthylmethane-6,6′-disulfonate. Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons, with the addition of one or more emulsifiers. Emulsifiers which can be used are, for example: calcium alkylarylsulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.

Dusting powders are obtained by grinding the active compound with finely divided solid substances, for example talc, naturally occurring clays, such as kaolin, bentonite and pyrophillite, or diatomaceous earth. Granules can be prepared either by spraying the active compound onto granular inert material capable of adsorption or by applying active compound concentrates to the surface of carrier substances, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils. Suitable active compounds can also be granulated in the manner customary for the preparation of fertilizer granules—if desired as a mixture with fertilizers.

In wettable powders, the active compound concentration is generally about 10 to 90% by weight, the remainder to make up 100% by weight comprising customary formulation constituents. In emulsifiable concentrates, the active compound concentration can be about 5 to 80% by weight. Dust-like formulations usually comprise 5 to 20% by weight of active compound, and sprayable solutions about 2 to 20% by weight. In granules, the content of active compound partly depends on whether the active compound is present in liquid or solid form and what granulating auxiliaries, fillers and the like are used.

In addition, the active compound formulations mentioned comprise, if appropriate, the particular customary tackifiers, wetting agents, dispersing agents, emulsifiers, penetration agents, solvents, fillers or carriers.

For use, the concentrates in the commercially available form are diluted in the customary manner, if appropriate, for example by means of water in the case of wettable powders, emulsifiable concentrates, dispersions and in some cases also microgranules. Dust-like and granular formulations as well as sprayable solutions are usually not diluted further with additional inert substances before use.

The required amount applied varies with external conditions, such as temperature, humidity and the like. It can vary within wide limits, for example between 0.0005 and 10.0 kg/ha or more of active substance, but is preferably between 0.001 and 5 kg/ha.

The active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from these formulations as mixtures with other active compounds, such as insecticides, attractants, sterilizing agents, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.

The pest control agents include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds, substances produced by microorganisms and the like.

Preferred partners for the mixtures are

1. from the group of phosphorus compounds

acephate, azamethiphos, azinphos-ethyl-, azinphosmethyl, bromophos, bromophos-ethyl, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, demeton, demeton-S-methyl, demeton-S-methyl sulfone, dialifos, diazinon, dichlorvos, dicrotophos, O,O-1,2,2,2-tetrachloroethyl phosphorthioate (SD 208 304), dimethoate, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitriothion, fensulfothion, fenthion, fonofos, formothion, heptenophos, isozophos, isothioate, isoxathion, malathion, methacrifos, methamidophos, methidathion, salithion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosfolan, phosmet, phosphamidon, phoxim, pirimiphos, primiphos-ethyl, pirimiphos-methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, sulprofos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorphon, vamidothion;

2. from the group of carbamates

aldicarb, 2-sec-butylphenyl methylcarbamate (BPMC), carbaryl, carbofuran, carbosulfan, cloethocarb, benfuracarb, ethiofencarb, furathiocarb, isoprocarb, methomyl, 5-methyl-m-cumenyl butyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, ethyl 4,6,9-triaza-4-benzyl-6,10-dimethyl-8-oxa-7-oxo-5,11-dithia-9-dodecenoate (OK 135), 1-methylthio(ethylideneamino) N-methyl-N-(morpholinothio)carbamate (UC 51717);

3. from the group of carboxylic acid esters

allethrin, alphametrin, 5-benzyl-3-furylmethyl (E)-(1R)-cis, 2,2-di-methyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), bioresmethrin, biphenate, (RS)-1-cyano-1-(6-phenoxy-2-pyridyl)methyl (1RS)-trans-3-(4-tert-butylphenyl)-2,2-dimethylcyclopropanecarboxylate (NCI 85193), cycloprothrin, cyhalothrin, cythithrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), permethrin, pheothrin ((R) isomer), d-pralethrin, pyrethrins (naturally occurring products), resmethrin, tefluthrin, tetramethrin and tralomethrin;

4. from the group of amidines

amitraz, chlordimeform;

5. from the group of tin compounds

cyhexatin, fenbutatin oxide;

6. others

abamectin, Bacillus thuringiensis , bensultap, binapacryl, bromopropylate, buprofezin, camphechlor, cartap, chlorobenzilate, chlorfluazuron, 2-(4-chlorophenyl)-4,5-diphenylthiophene (UBI-T 930), chlorfentezine, 2-naphthylmethyl cyclopropanecarboxylate (Ro 12-0470), cyromazin, N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propyloxy)phenyl)carbamoyl)-2-chlorobenzocarboximide acid ethyl ester, dicofol, N-(N-(3,5-di-chloro-4-(1,1,2,2-tetrafluoroethoxy)phenylamino)carbonyl)-2,6-difluorobenzamide (XRD 473), diflubenzuron, N-(2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene)-2,4-xylidene, dinobuton, dinocap, endosulfan, ethofenprox, (4-ethoxyphenyl)(dimethyl)(3-(3-phenoxyphenyl)propyl)silane, (4-ethoxyphenyl)(3-(4-fluoro-3-phenoxyphenyl)propyl)dimethylsilane, fenoxycarb, 2-fluoro-5-(4-(4-ethoxyphenyl)-4-methyl-1-pentyl)diphenyl ether (MTI 800), granulosis and nuclear polyhedrosis viruses, fenthiocarb, flubenzimine, flucycloxuron, flufenoxuron, gamma-HCH, hexythiazox, hydramethylnon (AC 217300), ivermectin, 2-nitromethyl-4,5-dihydro-6H-thiazine (DS 52618), 2-nitromethyl-3,4-dihydrothiazole (SD 35651), 2-nitromethylene-1,2-thiazinan-3-ylcarbamaldehyde (WL 108477), propargite, teflubenzuron, tetradifon, tetrasul, thiocyclam, trifumuron, imidacloprid.

The abovementioned combination partners are known active compounds, and most of them are described in Ch. R. Worthing, S. B. Walker, The Pesticide Manual, 7th Edition (1983), British Crop Protection Council.

The active compound content of the use forms prepared from the commercially available formulations can be from 0.00000001 to 95% by weight of active compound, preferably between 0.00001 and 1% by weight.

The active compounds are used in a customary manner appropriate for the use forms.

The active compounds according to the invention are also suitable for controlling endo- and ectoparasites in the veterinary medicine field and in the field of animal husbandry. The active compounds according to the invention are used here in a known manner, such as by oral use in the form of, for example, tablets, capsules, potions or granules, by means of dermal use in the form of, for example, dipping, spraying, pouring-on, spotting-on and dusting, and by parenteral use in the form of, for example, injection.

The novel compounds of the formula (I) can accordingly also particularly advantageously be used in livestock husbandry (for example cattle, sheep, pigs and poultry, such as chickens, geese and the like). In a preferred embodiment of the invention, the compounds are administered orally to the animals, if appropriate in suitable formulations (cf. above) and if appropriate with the drinking water or feed. Since excretion in the faeces takes place in an active manner, the development of insects in the faeces of the animals can be prevented very easily in this way. The dosages and formulations suitable in each case depend in particular on the species and the development stage of the stock animals and also on the pressure of infestation, and can easily be determined and specified by the customary methods. The novel compounds can be employed in cattle, for example, in dosages of 0.01 to 1 mg/kg of body weight.

In addition to the application methods mentioned hereinabove, the active compounds of the formula I according to the invention also have excellent systemic action. The active compounds can therefore also be introduced into the plants via below-ground and above-ground parts of plants (root, stem, leaf), when the active compounds are applied in liquid or solid form to the immediate surroundings of the plants (for example granules in soil application, application in flooded rice fields).

Furthermore, the active compounds according to the invention are particularly useful for treating vegetative and generatative propagation stock, such as, for example, seed of, for example, cereals, vegetables, cotton, rice, sugar beet and other crops and ornamentals, of bulbs, cuttings and tubers of other vegetatively propagated crops and ornamentals. To this end, treatment can be carried out prior to sowing or planting (for example by special seed coating techniques, by seed dressings in liquid or solid form or by seed box treatment), during sowing or planting or after sowing or planting by special application techniques (for example seed row treatment). Depending on the application, the amount of active compound applied can vary within a relatively wide range. In general, the application rates are between 1 g and 10 kg of active compound per hectare of soil area.

In a preferred embodiment, the invention provides 4-trifluoromethyl-3-oxadiazolyl, pyridine derivatives of the formula (I′),

where the symbols and indices are as defined below:

m is 0 or 1;

X is a single bond, a straight-chain alkylene group having 1, 2 or 3 carbon atoms or a branched alkylene group having 3 to 9 carbon atoms, where one or more H atoms may be replaced by F;

Y is —O—, —S—, —SO—, —SO 2 —, —O—CO—, —O—CO—O—, —SO 2 —O—, —O—SO 2 —, —NR 1 —, —NR 2 —CO—, —NR 3 —CO—O—, —NR 4 —CO—NR 5 —, —O—CO—CO—O—, —O—CO—NR 6 , —SO 2 —NR 7 or —NR 8 —SO 2 —;

R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are identical or different and are independently of one another H, (C 1 -C 10 )-alkyl, (C 2 -C 10 )-alkenyl, (C 2 -C 10 )-alkynyl, (C 3 -C 8 )-cycloalkyl, (C 4 -C 8 )-cycloalkenyl, (C 6 -C 8 )-cycloalkynyl, heterocyclyl or —(CH 2 ) 1-4 -heterocyclyl, where each of the eight last-mentioned groups is unsubstituted or mono- or polysubstituted, and where, optionally R and R 1 , R and R 2 , R and R 5 , R and R 6 , R and R 7 , R and R 8 or X and R together form a ring system,

with the proviso, that the compounds in which

X=-, Y=O, R=H

X=-, Y=O, R=Me

X=-, Y=O, R=Et

X=-, Y=O, R=CHF 2

X=-, Y=O, R=CH 2 Ph

X=CH 2 , Y=O, R=2-furanyl

X=CH 2 , Y=O, R=Me

X=CH 2 , Y=O, R=5-isoxazolyl

X=CH 2 , Y=O, R=5-nitrofuran-2-yl

X=CH 2 CH 2 , Y=O, R=H

X=CH 2 CH 2 ; Y=O, R=Me

X=CH 2 CH 2 , Y=O,

X=CH 2 CH 2 , Y=O, R=Et

X=CH 2 CH 2 , Y=O, R=H

X=CH 2 CH 2 ; Y=OC(O), R=4-F-phenyl

X=CH 2 CH 2 , Y=OC(O), R=2,6-difluorophenyl

X=CH 2 CH 2 , Y=OC(O), R=4-nitrophenyl

X=CH 2 CH 2 , Y=OC(O), R=t-Bu

X=CH 2 CH 2 , Y=OC(O), R=cyclopropyl

X=CH 2 CH 2 , Y=OC(O), R=Me

X=CH 2 CH 2 CH 2 , Y=O, R=H

X=-, Y=S(O), R=4-bromobenzyl

X=CH 2 , Y=S, R=Me

X=CH 2 , Y=S(O), R=Me

X=CH 2 , Y=S(O) 2 , R=t-Bu

X=CH 2 , Y=S, R=2-thienyl

X=CH 2 CH 2 , Y=S, R=Me

X=CH 2 CH 2 , Y=S, R=n-Pr

X=CH 2 CH 2 , Y=S, R=benzyl

X=CH 2 CH 2 , Y=S, R=2-thienylmethyl

X=CH 2 CH 2 CH 2 , Y=S, R=Me

X=CH 2 CH 2 CH 2 , Y=S(O), R=Me

X=CH 2 CH 2 CH 2 CH 2 , Y=S, R=CH 2 CH 2 CH 2 CH 2 OMe

are not included.

m is preferably 0.

If m is 1 and Y contains an S(O) n group, n is preferably 2.

X is preferably a single bond, CH 2 , CH 2 —CH 2 , CH 2 —CH(CH 3 ) or —CH 2 —C(CH 3 ) 2 —.

Y is preferably —O—, —S—, —SO—, —SO 2 —, —O—CO—, —O—CO—O, —O—CO—NR 6 —, —SO—NR 7 —, —O—Sμ 2 — or —SO 2 —O—.

R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are preferably identical or different and are independently of one another H, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 8 )-cycloalkyl, (C 4 -C 8 )-cycloalkenyl, (C 6 -C 8 )-cycloalkynyl, heterocyclyl or —(CH 2 ) 1-4 -heterocyclyl,

where the eight last-mentioned radicals are unsubstituted or substituted by one or more radicals from the group consisting of

halogen, cyano, citro, hydroxyl, —C(═W)R 9 , (═W), —C(═NOR 9 )R 9 , —C(═NNR 9 2 )R 9 , —C(═W)OR 9 , —C(═W)NR 9 2 , —OC(═W)R 9 , —OC(═W)OR 9 , —NR 9 C(═W)R 9 , —N[C(═W)R 9 ] 2 , —NR 9 C(═W)OR 9 , —C(═W)NR 9 —NR 9 2 , —C(═W)NR 9 —NR 9 [C(═W)R 9 ], —NR 9 —C(═W)NR 9 2 , —NR 9 —NR 9 C(═W)R 9 , —NR 9 —N[C(═W)R 9 ] 2 , —N[(C═W)R 9 ]—NR 9 2 , —NR 9 —N[(C═W)R 9 ] 2 , —NR 9 —NR 9 [(C═W)WR 9 ], —NR 9 —[(C═W)NR 9 2], —NR 9 (C═NR 9 )R 9 , —NR 9 (C═NR 9 )NR 9 2 , —O—NR 9 2 , —O—NR 9 (C═W)R 9 , —SO 2 NR 9 2 , —NR 9 SO 2 R 9 , —SO 2 OR 9 , —OSO 2 R 9 , —OR 9 , —NR 9 2 , —SR 9 , —SiR 9 3 , —SeR 9 , —PR 9 2 , —P(═W)R 9 2 , —SOR 9 , —SO 2 R 9 , —PW 2 R 9 2 , —PW 3 R 9 2 , aryl and heterocyclyl,

the two last-mentioned radicals of which are unsubstituted or substituted by one or more radicals from the group consisting of

(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 8 )-cycloalkyl, (C 4 -C 8 )-cycloalkenyl, (C 6 -C 8 )-cycloalkynyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-haloalkynyl, halogen, —OR 10 , —NR 10 2 , —SR 10 , —SiR 10 3 , —C(═W)R 10 , —C(═W)OR 10 , —C(═W)NR 10 2 , —SOR 10 , —SO 2 R 10 , nitro, cyano and hydroxyl,

and where optionally R and R 1 , R and R 5 , R and R 6 , R and R 7 and R and R 8 together are —(CH 2 ) 4 —, —(CH 2 ) 5 —, —(CH 2 ) 2 —O—(CH 2 ) 2 —, (CH 2 ) 2 —NR 2 —(CH 2 ) 2 —

and where X and R together, if appropriate, may also form a ring system,

and where optionally R and R 1 , R and R 2 , R and R 5 , R and R 6 , R and R 7 , R and R 8 or X and R together form a ring system.

Preferred to form the ring system are —(CH 2 ) 3 —, —(CH 2 ) 4 —, —(CH 2 ) 5 —, —(CH 2 ) 2 —O—(CH 2 ) 2 —, —(CH 2 ) 2 —NR 3 —(CH 2 ) 2 —, -(thiophen-3,4-diyl)—C(O)—, CH(imidazolyl-)CF 2 C(O)—, —CH(Me)CH 2 C(O)—, —CMe 2 CH 2 C(O)—, —CH(Me)CH(Me)C(O)—, —CH 2 CH 2 CH 2 C(O)—, —CH(Me)CH 2 CH 2 C(O)—, —CH 2 CH(Me)CH 2 C(O)—, —CH 2 CMe 2 CH 2 C(O)—, —CH 2 C[—(CH 2 ) 4 —]CH 2 C(O)—, -(1,2-cyclohexylene)-C(O)—, -(cyclohexene-4,5-diyl)-C(O)—, —CH 2 —C(H)Ph—CH 2 —C(O)—, —CMe═CMe—C(O)—, —CH 2 —CH 2 —C(O)—, especially preferred are —(CH 2 ) 3 —, —(CH 2 ) 4 —, —(CH 2 ) 5 —, —(CH 2 ) 2 —O—(CH 2 ) 2 —, —(CH 2 ) 2 —NR 3 —(CH 2 ) 2 —.

W is O or S.

R 9 is hydrogen,

(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 8 )-cycloalkyl, (C 4 -C 8 )-cycloalkenyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkyl, (C 3 -C 8 )-cycloalkyl-(C 2 -C 4 )-alkenyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkenyl, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkyl, (C 2 -C 6 )-alkenyl-(C 3 -C 8 )-cycloalkyl, (C 2 -C 6 )-alkynyl-(C 3 -C 8 )-cycloalkyl, (C 1 -C 6 )-alkyl-(C 4 -C 8 )-cycloalkenyl, (C 2 -C 6 )-alkenyl-(C 4 -C 8 )-cycloalkenyl,

where the fourteen last-mentioned radicals are unsubstituted or substituted by one or more radicals from the group consisting of

halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkenyloxy, (C 2 -C 6 )-alkynyloxy, (C 1 -C 6 )-haloalkyloxy, (C 2 -C 6 )-haloalkenyloxy, (C 2 -C 6 )-haloalkynyloxy, (C 3 -C 8 )-cycloalkoxy, (C 4 -C 8 )-cycloalkenyloxy, (C 3 -C 8 )-halocycloalkoxy, (C 4 -C 8 )-halocycloalkenyloxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkoxy, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkoxy, (C 3 -C 8 )-cycloalkyl-(C 2 -C 4 )-alkenyloxy, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkenyloxy, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkoxy, (C 2 -C 6 )-alkenyl-(C 3 -C 8 )-cycloalkoxy, (C 2 -C 6 )-alkynyl-(C 3 -C 8 )-cycloalkoxy, (C 1 -C 6 )-alkyl-(C 4 -C 8 )-cycloalkenyloxy, (C 2 -C 6 )-alkenyl-(C 4 -C 8 )-cycloalkenyloxy, (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkoxy, (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkenyloxy, carbamoyl, (C 1 -C 6 )-mono- or -dialkylcarbamoyl, (C 1 -C 6 )-mono- or dihaloalkylcarbamoyl, (C 3 -C 8 )-mono- or dicycloalkylcarbamoyl, (C 1 -C 6 )-alkoxycarbonyl, (C 3 -C 8 )-cycloalkoxycarbonyl, (C 1 -C 6 )-alkanoyloxy, (C 3 -C 8 )-cycloalkanoyloxy, (C 1 -C 6 )-haloalkoxycarbonyl, (C 1 -C 6 )-haloalkanoyloxy, (C 1 -C 6 )-alkanamido, (C 1 -C 6 )-haloalkanamido, (C 2 -C 6 )-alkenamido, (C 3 -C 8 )-cycloalkanamido, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkanamido, (C 1 -C 6 )-alkylthio, (C 2 -C 6 )-alkenylthio, (C 2 -C 6 )-alkynylthio, (C 1 -C 6 )-haloalkylthio, (C 2 -C 6 )-haloalkenylthio, (C 2 -C 6 )-haloalkynylthio, (C 3 -C 8 )-cycloalkylthio, (C 4 -C 8 )-cycloalkenylthio, (C 3 -C 8 )-halocycloalkylthio, (C 4 -C 8 )-halocycloalkenyllthio, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkylthio, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkylthio, (C 3 -C 8 )-cycloalkyl-(C 2 -C 4 )-alkenylthio, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkenylthio, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkylthio, (C 2 -C 6 )-alkenyl-(C 3 -C 8 )-cycloalkylthio, (C 2 -C 6 )-alkynyl-(C 3 -C 8 )-cycloalkylthio, (C 1 -C 6 )-alkyl-(C 4 -C 8 )-cycloalkenylthio, (C 2 -C 6 )-alkenyl-(C 4 -C 8 )-cycloalkenylthio, (C 1 -C 6 )-alkylsulfinyl, (C 2 -C 6 )-alkenylsulfinyl, (C 2 -C 6 )-alkynylsulfinyl, (C 1 -C 6 )-haloalkylsulfinyl, (C 2 -C 6 )-haloalkenylsulfinyl, (C 2 -C 6 )-haloalkynylsulfinyl, (C 3 -C 8 )-cycloalkylsulfinyl, (C 4 -C 8 )-cycloalkenylsulfinyl, (C 3 -C 8 )-halocycloalkylsulfinyl, (C 4 -C 8 )-halocycloalkenylsulfinyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkylsulfinyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkylsulfinyl, (C 3 -C 8 )-cycloalkyl-(C 2 -C 4 )-alkenylsulfinyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkenylsulfinyl, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkylsulfinyl, (C 2 -C 6 )-alkenyl-(C 3 -C 8 )-cycloalkylsulfinyl, (C 2 -C 6 )-alkynyl-(C 3 -C 8 )-cycloalkylsulfinyl, (C 1 -C 6 )-alkyl-(C 4 -C 8 )-cycloalkenylsulfinyl, (C 2 -C 6 )-alkenyl-(C 4 -C 8 )-cycloalkenylsulfinyl, (C 1 -C 6 )-alkylsulfonyl, (C 2 -C 6 )-alkenylsulfonyl, (C 2 -C 6 )-alkynylsulfonyl, (C 1 -C 6 )-haloalkylsulfonyl, (C 2 -C 6 )-haloalkenylsulfonyl, (C 2 -C 6 )-haloalkynylsulfonyl, (C 3 -C 8 )-cycloalkylsulfonyl, (C 4 -C 8 )-cycloalkenylsulfonyl, (C 3 -C 8 )-halocycloalkylsulfonyl, (C 4 -C 8 )-halocycloalkenylsulfonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkylsulfonyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkylsulfonyl, (C 3 -C 8 )-cycloalkyl-(C 2 -C 4 )-alkenylsulfonyl, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkenylsulfonyl, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkylsulfonyl, (C 2 -C 6 )-alkenyl-(C 3 -C 8 )-cycloalkylsulfonyl, (C 2 -C 6 )-alkynyl-(C 3 -C 8 )-cycloalkylsulfonyl, (C 1 -C 6 )-alkyl-(C 4 -C 8 )-cycloalkenylsulfonyl, (C 1 -C 6 )-alkylamino, (C 2 -C 6 )-alkenylamino, (C 2 -C 6 )-alkynylamino, (C 1 -C 6 )-haloalkylamino, (C 2 -C 6 )-haloalkenylamino, (C 2 -C 6 )-haloalkynylamino, (C 3 -C 8 )-cycloalkylamino, (C 4 -C 8 )-cycloalkenylamino, (C 3 -C 8 )-halocycloalkylamino, (C 4 -C 8 )-halocycloalkenylamino, (C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkylamino, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkylamino, (C 3 -C 8 )-cycloalkyl-(C 2 -C 4 )-alkenylamino, (C 4 -C 8 )-cycloalkenyl-(C 1 -C 4 )-alkenylamino, (C 1 -C 6 )-alkyllkylamino, (C 2 -C 6 )-alkenyl-(C 3 -C 8 )-cycloalkylamino, (C 2 -C 6 )-alkynyl-(C 3 -C 8 )-cycloalkylamino, (C 1 -C 6 )-alkyl-(C 4 -C 8 )-cycloalkenylamino, (C 2 -C 6 )-alkenyl-(C 4 -C 8 )-cycloalkenylamino, (C 1 -C 6 )-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, aryl-(C 1 -C 4 )-alkoxy, aryl-(C 2 -C 4 )-alkenyloxy, aryl-(C 1 -C 4 )-alkylthio, aryl-(C 2 -C 4 )-alkenylthio, aryl-(C 1 -C 4 )-alkylamino, aryl-(C 2 -C 4 )-alkenylamino, aryl-(C 1 -C 6 )-dialkylsilyl, diaryl-(C 1 -C 6 )-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl,

where the cyclic moiety of the fourteen last-mentioned radicals is unsubstituted or substituted by one or more radicals from the group consisting of

halogen, cyano, nitro, amino, hydroxyl, thio, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 3 -C 8 )-cycloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-haloalkylthio, (C 1 -C 4 )-alkylamino, (C 1 -C 4 )-haloalkylamino, formyl and (C 1 -C 4 )-alkanoyl,

aryl, 4-, 5- or 6-membered heterocyclyl,

where the two last-mentioned radicals are unsubstituted or substituted by one or more radicals from the group consisting of

halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkenyloxy, (C 2 -C 6 )-alkynyloxy, (C 1 -C 6 )-haloalkyloxy, (C 2 -C 6 )-haloalkenyloxy, (C 2 -C 6 )-haloalkynyloxy, (C 3 -C 8 )-cycloalkoxy, (C 4 -C 8 )-cycloalkenyloxy, (C 3 -C 8 )-halocycloalkoxy, (C 4 -C 8 )-halocycloalkenyloxy, carbamoyl, (C 1 -C 6 )-mono- or -dialkylcarbamoyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkanoyloxy, (C 1 -C 6 )-mono- or -dihaloalkylcarbamoyl, (C 1 -C 6 )-haloalkoxycarbonyl, (C 1 -C 6 )-haloalkanoyloxy, (C 1 -C 6 )-alkanamido, (C 1 -C 6 )-haloalkanamido, (C 2 -C 6 )-alkenamido, (C 1 -C 6 )-alkylthio, (C 2 -C 6 )-alkenylthio, (C 2 -C 6 )-alkynylthio, (C 1 -C 6 )-haloalkylthio, (C 2 -C 6 )-haloalkenylthio, (C 2 -C 6 )-haloalkynylthio, (C 3 -C 8 )-cycloalkylthio, (C 4 -C 8 )-cycloalkenylthio, (C 3 -C 8 )-halocycloalkylthio, (C 4 -C 8 )-halocycloalkenylthio, (C 1 -C 6 )-alkylsulfinyl, (C 2 -C 6 )-alkenylsulfinyl, (C 2 -C 6 )-alkynylsulfinyl, (C 1 -C 6 )-haloalkylsulfinyl, (C 2 -C 6 )-haloalkenylsulfinyl, (C 2 -C 6 )-haloalkynylsulfinyl, (C 3 -C 8 )-cycloalkylsulfinyl, (C 4 -C 8 )-cycloalkenylsulfinyl, (C 3 -C 8 )-halocycloalkylsulfinyl, (C 4 -C 8 )-halocycloalkenylsulfinyl, (C 1 -C 6 )-alkylsulfonyl, (C 2 -C 6 )-alkenylsulfonyl, (C 2 -C 6 )-alkynylsulfonyl, (C 1 -C 6 )-haloalkylsulfonyl, (C 2 -C 6 )-haloalkenylsulfonyl, (C 2 -C 6 )-haloalkynylsulfonyl, (C 3 -C 8 )-cycloalkylsulfonyl, (C 4 -C 8 )-cycloalkenylsulfonyl, (C 3 -C 8 )-halocycloalkylsulfonyl, (C 4 -C 8 )-halocycloalkenylsulfonyl, (C 1 -C 6 )-alkylamino, (C 2 -C 6 )-alkenylamino, (C 2 -C 6 )-alkynylamino, (C 1 -C 6 )-haloalkylamino, (C 2 -C 6 )-haloalkenylamino, (C 2 -C 6 )-haloalkynylamino, (C 3 -C 8 )-cycloalkylamino, (C 4 -C 8 )-cycloalkenylamino, (C 3 -C 8 )-halocycloalkylamino and (C 4 -C 8 )-halocycloalkenylamino.

R and R 1 -R 8 are particularly preferably H, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, heterocyclyl, where the four last-mentioned radicals are unsubstituted or substituted by one or more, preferably by one to four, radicals from the group consisting of halogen, preferably F, CN, SiMe 3 , —O—(C 1 -C 6 )-alkyl, —S—(C 1 -C 6 )-alkyl or —O—CO—(C 1 -C 6 )-alkyl.

Very particular preference is given to compounds of the formulae I′-1 to 1′-32, also in the form of their pyridine N-oxides, where the symbols and indices are as defined above:

Preference is likewise given to the corresponding formulae I′-33 to I′-96 in which Y is —CH 2 CH 2 —, —CH 2 —CH(CH 3 )—, —CH 2 —CH 2 —CH 2 — and —CH 2 —C(CH 3 ) 2 —.

The term “halogen” includes fluorine, chlorine, bromine and iodine.

The term “(C 1 -C 4 )-alkyl” is to be understood as a straight-chain or branched hydrocarbon radical having 1, 2, 3 or 4 carbon atoms, such as, for example, the methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radical. Correspondingly, alkyl radicals having a greater range of carbon atoms are to be understood as straight-chain or branched saturated hydrocarbon radicals which contain a number of carbon atoms which corresponds to the range stated. Thus, the term “(C 1 -C 6 )-alkyl” includes the abovementioned alkyl radicals, and, for example, the pentyl, 2-methylbutyl, 1,1-dimethylpropyl and hexyl radical. The term “(C 1 -C 10 )-alkyl” is to be understood as the abovementioned alkyl radicals, and, for example, the nonyl, 1-decyl or 2-decyl radical.

“(C 1 -C 4 )-Haloalkyl” is to be understood as an alkyl group mentioned under the term “(C 1 -C 4 )-alkyl” in which one or more hydrogen atoms are replaced by the same number of identical or different halogen atoms, preferably chlorine or fluorine, such as the trifluoromethyl, the 1-fluoroethyl, the 2,2,2-trifluoroethyl, the chloromethyl, fluoromethyl, the difluoromethyl and the 1,1,2,2-tetrafluoroethyl group.

“(C 1 -C 4 )-Alkoxy” is to be understood as an alkoxy group whose hydrocarbon radical has the meaning given under the term “(C 1 -C 4 )-alkyl”. Alkoxy groups embracing a greater range of carbon atoms are to be understood correspondingly.

The terms “alkenyl” and “alkynyl” having a prefix stating the range of carbon atoms denote a straight-chain or branched hydrocarbon radical having a number of carbon atoms corresponding to the range stated which comprises at least one multiple bond which may be in any position of the unsaturated radical in question. “(C 2 -C 4 )-Alkenyl” is thus, for example, the vinyl, allyl, 2-methyl-2-propene or 2-butenyl group; “(C 2 -C 6 )-alkenyl” denotes the abovementioned radicals and, for example, the pentenyl, 2-methylpentenyl or the hexenyl group. “(C 2 -C 4 )-Alkynyl” is, for example, the ethynyl, propargyl, 2-methyl-2-propyne or 2-butynyl group. “(C 2 -C 6 )-Alkynyl” is to be understood as the abovementioned radicals and, for example, the 2-pentynyl or the 2-hexynyl group and “(C 2 -C 10 )-alkynyl” is to be understood as the abovementioned radicals and, for example, the 2-octynyl or the 2-decynyl group.

“(C 3 -C 8 )-Cycloalkyl” denotes monocyclic alkyl radicals, such as the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radical and bicyclic alkyl radicals, such as the norbornyl radical.

The term “(C 3 -C 8 )-cycloalkyl-(C 1 -C 4 )-alkyl” is to be understood as, for example, the cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylbutyl radical, and the term “(C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkyl is to be understood as, for example, the 1-methylcyclopropyl, 1-methylcyclopentyl, 1-methylcyclohexyl, 3-hexylcyclobutyl and 4-tert-butyl-cyclohexyl radical.

“(C 1 -C 4 )-Alkoxy-(C 1 -C 6 )-alkyloxy” is an alkoxy group as defined above which is substituted by a further alkoxy group, such as, for example, 1-ethoxyethoxy.

“(C 3 -C 8 )-Cycloalkoxy” or “(C 3 -C 8 )-cycloalkylthio” is to be understood as one of the abovementioned (C 3 -C 8 )-cycloalkyl radicals which is linked via an oxygen or sulfur atom.

“(C 3 -C 8 )-Cycloalkyl-(C 1 -C 6 )-alkoxy” is, for example, the cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclohexylethoxy or the cyclohexylbutoxy group.

The term “(C 1 -C 4 )-alkyl-(C 3 -C 8 )-cycloalkoxy” is, for example, the methylcyclopropyloxy, methylcyclobutyloxy or the butylcyclohexyloxy group.

“(C 1 -C 6 )-Alkylthio” is an alkylthio group whose hydrocarbon radical has the meaning given under the term “(C 1 -C 6 )-alkyl”.

Correspondingly, “(C 1 -C 6 )-alkylsulfinyl” is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfinyl group and “(C 1 -C 6 )-alkylsulfonyl” is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfonyl group.

“(C 1 -C 6 )-Alkylamino” is a nitrogen atom which is substituted by one or two identical or different alkyl radicals of the above definition.

The term “(C 1 -C 6 )-mono- or -dialkylcarbamoyl” is a carbamoyl group having one or two hydrocarbon radicals which have the meaning given under the term “(C 1 -C 6 -alkyl)” and which, in the case of two hydrocarbon radicals, may be identical or different.

Correspondingly, “(C 1 -C 6 )-dihaloalkylcarbamoyl” is a carbamoyl group which carries two (C 1 -C 6 )-haloalkyl radicals in accordance with the above definition or one (C 1 -C 6 )-haloalkyl radical and one (C 1 -C 6 )-alkyl radical in accordance with the above definition.

“(C 1 -C 6 )-Alkanoyl” is, for example, the acetyl, propionyl, butyryl or 2-methylbutyryl group.

The term “aryl” is to be understood as a carbocyclic, i.e. constructed from carbon atoms, aromatic radical preferably having 6 to 14, in particular 6 to 12, carbon atoms, such as, for example, phenyl, naphthyl or biphenylyl, preferably phenyl. “Aroyl” is thus an aryl radical as defined above which is attached via a carbonyl group, such as, for example, the benzoyl group.

The term “heterocyclyl” preferably denotes a cyclic radical which may be fully saturated, partially unsaturated or fully unsaturated and which may be interrupted by at least one or more identical or different atoms from the group consisting of nitrogen, sulfur or oxygen, two oxygen atoms, however, not being allowed to be directly adjacent to one another and at least one carbon atom having to be present in the ring, such as, for example, a thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3,4-triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo[b]thiophene, benzo[b]furan, indole, benzo[c]thiophene, benzo[c]furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, pyridine, pyrazine, pyrimidine, pyridazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,4,5-tetrazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine, 4H-quinolizine; piperidine, pyrrolidine, oxazoline, tetrahydrofuran, tetrahydropyran, isoxazolidine or thiazolidine radical. The term “heteroaromatic” thus embraces, from among the meanings mentioned above under “heterocyclyl”, in each case the fully unsaturated aromatic heterocyclic compounds.

Heterocyclyl is particularly preferably a saturated, partially saturated or aromatic ring system having 3 to 6 ring members and 1 to 4 heteroatoms from the group consisting of O, S and N, wherein at least one of the ring members is carbon.

Heterocyclyl is very particularly preferably a radical of pyridine, pyrimidine, (1,2,4)-oxadiazole, (1,3,4)-oxadiazole, pyrrole, furan, thiophene, oxazole, thiazole, imidazole, pyrazole, isoxazole, 1,2,4-triazole, tetrazole, pyrazine, pyridazine, oxazoline, thiazoline, tetrahydrofuran, tetrahydropyran, morpholine, piperidine, piperazine, pyrroline, pyrrolidine, oxazolidine, thiazolidine, oxirane and oxetane.

“Aryl-(C 1 -C 4 )-alkoxy” is an aryl radical which is attached via a (C 1 -C 4 )-alkoxy group, for example the benzyloxy, phenylethoxy, phenylbutoxy or naphthylmethoxy radical.

“Arylthio” is an aryl radical attached via a sulfur atom, for example the phenylthio or the 1- or 2-naphthylthio radical. Correspondingly, “aryloxy” is, for example, the phenoxy or 1- or 2-naphthyloxy radical.

“Aryl-(C 1 -C 4 )-alkylthio” is an aryl radical which is attached via an alkylthio radical, for example the benzylthio, naphthylmethylthio or the phenylethylthio radical.

The term “(C 1 -C 6 )-trialkylsilyl” denotes a silicon atom which carries three identical or different alkyl radicals in accordance with the above definition. Correspondingly “aryl-(C 1 -C 6 )-dialkylsilyl” is a silicon atom which carries one aryl radical and two identical or different alkyl radicals in accordance with the above definition, “diaryl-(C 1 -C 6 )-alkylsilyl” is a silicon atom which carries one alkyl radical and two identical or different aryl radicals in accordance with the above definition, and “triarylsilyl” is a silicon atom which carries three identical or different aryl radicals in accordance with the above definition.

In cases where two or more radicals R 9 are present in a substituent, such as, for example, in —C(═W)NR 9 2 , these radicals may be identical or different.

Depending on the nature of the substituents defined above, the compounds of the formula (I′) have acidic or basic properties and can form salts. If the compounds of the formula (I′) carry, for example, groups such as hydroxyl, carboxyl or other groups inducing acidic properties, these compounds can be reacted with bases to give salts. Suitable bases are, for example, hydroxides, carbonates, bicarbonates of the alkali metals and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, further ammonia, primary, secondary and tertiary amines having (C 1 -C 4 )-alkyl radicals and also mono-, di- and trialkanolamines of (C 1 -C 4 )-alkanols. If the compounds of the formula (I′) carry, for example, groups such as amino, alkylamino or other groups inducing basic properties, these compounds can be reacted with acids to give salts. Suitable acids are, for example, mineral acids, such as hydrochloric acid, sulfuric acid and phosphoric acid, organic acids, such as acetic acid and oxalic acid, and acidic salts, such as NaHSO 4 and KHSO 4 . The salts which can be obtained in this manner likewise have insecticidal, acaricidal and nematicidal properties.

The compounds of the formula (I′) may have one or more asymmetric carbon atoms or stereoisomers on double bonds. Enantiomers or diastereomers may therefore be present. The invention embraces both the pure isomers and mixtures thereof. The mixtures of diastereomers can be separated into the isomers by customary methods, for example by selective crystallization from suitable solvents or by chromatography. Racemates can be separated into the enantiomers by customary methods.

The compounds according to the invention are prepared according to methods which are known per se from the literature, as described in standard works on organic synthesis, for example Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart.

The preparation is carried out under reaction conditions which are known and suitable for the reactions mentioned. It is also possible to employ variants which are known per se but not mentioned in more detail here.

If desired, the starting materials can also be formed in situ, such that they are not isolated from the reaction mixture but are immediately reacted further to give the compounds of the formula (I′).

For preparing compounds of the formula (I′), for example, activated derivatives of the acid of the formula (II′),

are reacted in the presence of a base with a compound of the formula (III′),

in which the radical X—Y—R is as defined in formula (I′) or corresponds to a precursor of such a radical. The activated derivative used can be, for example, an acyl halide, an ester or an anhydride. Suitable bases are amines, such as triethylamine, diisopropylethylamine, pyridine or lutidine, alkali metal hydroxides, alkali metal alkoxides, such as sodium ethoxide or potassium tert-butoxide, or alkyl metal compounds, such as butyllithium.

Depending on the conditions selected, the described reaction can be carried out as a one-step process or as a two-step process, the intermediates being compounds of the formula (IV′):

Compounds of the formula (IV′) can be cyclized to the 1,2,4-oxadiazoles by heating in an inert solvent at temperatures of up to 180° C. and by addition of dehydrating agents (for example Amberlyst).

Compounds of the formula (IV′) are also directly obtainable from the acid of the formula (II′) and amidoximes of the formula (III′) by using a dehydrating agent, such as dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylamino-propyl)carbodiimide or N,N′-carbonyldiimidazole.

Both trifluoromethylnicotinic acid (II′) and amidoximes of the formula (III′) are commercially available or can be prepared by processes known from the literature (see, for example: Houben-Weyl, Methoden der organischen Chemie, Volume X/4, pages 209-212; EP-A 0 580 374; G. F. Holland, J. N. Pereira, J. Med. Chem., 1967, 10, 149).

After the oxadiazolyl group has been constructed, as shown in the following reaction schemes for example by condensation, cyclization or cycloaddition reactions, the radical R can, if desired, be derivatized further, it being possible to employ the broad range of methods of organochemical synthesis.

Central intermediates of ethers, thioethers and analogous derivatives are haloalkyl- or hydroxyalkyl-substituted oxadiazole derivatives of the formula (V′),

which can then be converted into the corresponding target compounds using standard processes of organic synthesis.

Ethers of the formula (I′) are obtainable by etherifying corresponding hydroxyl compounds where the hydroxyl compound is advantageously initially converted into a corresponding metal derivative, for example into the corresponding alkali metal alkoxide by treatment with NaH, NaNH 2 , NaOH, KOH, Na 2 CO 3 . The alkali metal alkoxide or alkali metal phenolate can then be reacted with the appropriate alkyl halide, alkyl sulfonate or dialkyl sulfate, advantageously in an inert solvent, such as acetone, 1,2-dimethoxyethane, DMF or dimethyl sulfoxide, or else in an excess of aqueous or aqueous-alcoholic NaOH or KOH, at temperatures between about 20° C. and 100° C.

Derivatives of the amino compound (VI′) can be prepared, for example, by reacting the chloro compound ((V′), V′=Cl) with amines or via the central intermediate ((V′); V′=NH 2 ).

The synthesis of the central intermediate ((V′); V′=NH 2 ) is effected by reacting the chloro derivative ((V′; V=Cl) with ammonia in the presence of a suitable base or, preferably by reacting the chloro derivative ((V′); V′=Cl) with potassium phthalimide and subsequent hydrazinolysis. Further derivatisation of this central intermediate ((V′); V′=NH 2 ) is effected by the reaction with suitable electrophiles.

For preparing the sulfoxides ((VII′); n=1) and the sulfones ((VII′); n=2), the corresponding thioethers of the formula (VII′) (n=0) are, for example, employed:

The synthesis is carried out by oxidation with an oxidizing agent, for example meta-chloroperbenzoic acid, with an appropriately selected stoichiometry and temperature.

The synthesis of alkylester substituted oxadiazol derivatives (VIII′) is effected, e.g. by the substitution of chlorine in ((V′); V′=Cl) by alkalicarboxylates or the esterification of the hydroxyalkyl-oxadiazol ((V′); V′=OH) with activated derivatives of carboxylic acids.

Starting from the hydroxyalkyl oxadiazol ((V′); V′=OH) the respective sulfonates can be prepared analogously:

To prepare sulfonamides (X′) the chloroalkyl compound ((V′); V′=Cl) is converted to the respective sodium sulfonate (IX′) with the acid of sodium sulfite, which the can be further derivatized to the desired sulfonamide (X′).

Collections of compounds of the formula (I′) which can be synthesized by the abovementioned scheme may also be prepared in a parallel manner and this may be effected manually or in a semiautomated or fully automated manner. In this case, it is possible, for example, to automate the procedure of the reaction, the work-up or the purification of the products or of the intermediates. In total, this is to be understood as meaning a procedure as is described, for example, by S. H. DeWitt in “Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated Synthesis”, Volume 1, Verlag Escom 1997, pages 69 to 77.

A number of commercially available apparatuses as they are offered by, for example, Stem Corporation, Woodrolfe Road, Tollesbury, Essex, CM9 8SE, England, H+P Labortechnik GmbH, Bruckmannring 28, 85764 Oberschleiβheim, Germany or Radleys, Shirehill, Saffron Walden, Essex, England may be used for the parallel procedure of the reaction and work-up. For the parallel purification of compounds of the formula (I′), or of intermediates obtained during the preparation, use may be made, inter alia, of chromatography apparatuses, for example those from ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA.

The apparatuses mentioned lead to a modular procedure in which the individual process steps are automated, but manual operations have to be performed between the process steps. This can be avoided by employing semi-integrated or fully integrated automation systems where the automation modules in question are operated by, for example, robots. Such automation systems can be obtained, for example, from Zymark Corporation, Zymark Center, Hopkinton, Mass. 01748, USA.

In addition to what has been described here, compounds of the formula (I′) may be prepared in part or fully by solid-phase-supported methods. For this purpose, individual intermediate steps or all intermediate steps of the synthesis or of a synthesis adapted to suit the procedure in question are bound to a synthetic resin. Solid-phase-supported synthesis methods are described extensively in the specialist literature, for example Barry A. Bunin in “The Combinatorial Index”, Verlag Academic Press, 1998.

The use of solid-phase-supported synthesis methods permits a series of protocols which are known from the literature and which, in turn, can be performed manually or in an automated manner. For example, the “tea-bag method” (Houghten, U.S. Pat. No. 4,631,211; Houghten et al., Proc. Natl. Acad. Sci, 1985, 82, 5131-5135), in which products from IRORI, 11149 North Torrey Pines Road, La Jolla, Calif. 92037, USA, are employed, may be semiautomated. The automation of solid-phase-supported parallel syntheses is performed successfully, for example, by apparatuses from Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, Calif. 94070, USA or MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Germany.

The preparation according to the processes described herein yields compounds of the formula (I′) in the form of substance collections which are referred to as libraries. The present invention also relates to libraries which comprise at least two compounds of the formula (I′).

The compounds of the formula (I′) are suitable for controlling animal pests, in particular insects, arachnids, helminths and mollusks, very especially preferably for controlling insects and arachnids, which are encountered in agriculture, in livestock breeding, in forests, in the protection of stored goods and materials and in the hygiene sector, and have good plant tolerance and favorable toxicity to warm-blooded species. They are active against normally sensitive and resistant species and against all or individual development stages. The abovementioned pests include:

From the order of the Acarina, for example, Acarus siro , Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora , Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa , Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp. and Eutetranychus spp.

From the order of the Isopoda, for example, Oniscus asselus, Armadium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea madeira, Blattella germanica, Acheta domesticus , Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Phylloera vastatrix , Pemphigus spp., Pediculus humanus corporis , Haematopinus spp. and Linognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae , Myzus spp., Phorodon humuli, Rhopalosiphum padi , Empoasca spp., Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae , Pseudococcus spp. and Psylla spp.

From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea , Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella , Agrotis spp., Euxoa spp., Feltia spp., Earias insulana , Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura , Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella , Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima and Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae , Diabrotica spp., Psylloides chrysocephala, Epilachna varivestis , Atomaria spp., Oryzaephilus surinamensis , Anthonumus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrynchus assimilis, Hypera postica , Dermestes spp., Trogoderma, Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus , Ptinus spp., Niptus hololeucus, Gibbium psylloides , Tribolium spp., Tenebrio molitor , Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis and Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster , Musca spp., Fannia spp., Calliphora erythiocephala , Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit , Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopsis and Ceratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans.

From the class of helminths, for example, Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis, as well as Fasciola.

From the class of the Gastropoda, for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp. and Oncomelania spp.

From the class of Bivalva, for example, Dreissena spp.

The phytoparasitic nematodes which can be controlled according to the invention include, for example, the root-parasitic soil nematodes, such as, for example, those of the genera Meloidogyne (root gall nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica ), Heterodera and Globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera pallida and Heterodera trifolii ) and of the genera Radopholus, such as Radopholus similis , Pratylenchus, such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus ; Tylenchulus, such as Tylenchulus semipenetrans , Tylenchorhynchus, such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni , Rotylenchus, such as Rotylencus robustus , Heliocotylenchus, such as Heliocotylenchus multicinctus , Belonoaimus, such as Belonoaimus longicaudatus , Longidorus, such as Longidorus elongatus , Trichodorus, such as Trichodorus primitivus and Xiphinema, such as Xiphinema index.

The nematode genera Ditylenchus (stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor ), Aphelenchoides (leaf nematodes, such as Aphelenchoides ritzemabosi ) and Anguina (blossom nematodes, such as Anguina tritici ) can furthermore be controlled with the compounds according to the invention.

The invention also relates to compositions, for example crop protection compositions, preferably insecticidal, acaricidal, ixodicidal, nematicidal, molluskidal or fungicidal, particularly preferably insecticidal and acaricidal compositions, which comprise one or more compounds of the formula (I′) in addition to suitable formulation auxiliaries.

In general, the compositions according to the invention comprise from 1 to 95% by weight of the active compounds of the formula (I′).

For preparing the compositions according to the invention, the active compound and the other additives are combined and formulated as a suitable use form.

The invention also relates to compositions, in particular insecticidal and acaricidal compositions, which comprise the compounds of the formula (I′) in addition to suitable formulation auxiliaries.

The compositions according to the invention in general comprise from 1 to 95% by weight the active compounds of the formula (I′). They can be formulated in various ways, depending on how this is determined by the biological and/or chemico-physical parameters. Suitable formulation possibilities are therefore:

Wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions, sprayable solutions, oil- or water-based dispersions (SC), suspoemulsions (SE), dusting powders (DP), seed dressings, granules in the form of microgranules, sprayed granules, absorption granules and adsorption granules, water-dispersible granules (WG), ULV formulations, microcapsules, waxes or baits.

These individual types of formulation are known in principle and are described, for example, in: Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986; van Falkenberg, “Pesticides Formulations”, Marcel Dekker N.Y., 2nd Edition 1972-73; K. Martens, “Spray Drying Handbook”, 3rd Edition 1979, G. Goodwin Ltd. London.

The necessary formulation auxiliaries, i.e. carrier substances and/or surface-active substances, such as inert materials, surfactants, solvents and further additives, are likewise known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Edition, Darland Books, Caldwell N.J.; H. v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd Edition, J. Wiley & Sons, N.Y.; Marsden, “Solvents Guide”, 2nd Edition, Interscience, N.Y. 1950; McCutcheon's, “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1967; Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986.

Combinations with other substances having a pesticidal action, fertilizers and/or growth regulators can be prepared on the basis of these formulations, for example in the form of a ready-to-use formulation or as a tank mix. Wettable powders are preparations which are uniformly dispersible in water and which, alongside the active compound, and in addition to a diluent or inert substance, also comprise wetting agents, for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols or alkyl- or alkylphenolsulfonates, and dispersing agents, for example sodium ligninsulfonate or sodium 2,2′-dinaphthylmethane-6,6′-disulfonate. Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons, with the addition of one or more emulsifiers.

Emulsifiers which can be used are, for example: calcium alkylarylsulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.

Dusting powders are obtained by grinding the active compound with finely divided solid substances, for example talc, naturally occurring clays, such as kaolin, bentonite and pyrophillite, or diatomaceous earth. Granules can be prepared either by spraying the active compound onto granular inert material capable of adsorption or by applying active compound concentrates to the surface of carrier substances, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils. Suitable active compounds can also be granulated in the manner customary for the preparation of fertilizer granules—if desired as a mixture with fertilizers.

In wettable powders, the active compound concentration is generally about 10 to 90% by weight, the remainder to make up 100% by weight comprising customary formulation constituents. In emulsifiable concentrates, the active compound concentration can be about 5 to 80% by weight. Dust-like formulations usually comprise 5 to 20% by weight of active compound, and sprayable solutions about 2 to 20% by weight. In granules, the content of active compound partly depends on whether the active compound is present in liquid or solid form and what granulating auxiliaries, fillers and the like are used.

In addition, the active compound formulations mentioned comprise, if appropriate, the particular customary tackifiers, wetting agents, dispersing agents, emulsifiers, penetration agents, solvents, fillers or carrier substances.

For use, the concentrates in the commercially available form are diluted in the customary manner, if appropriate, for example by means of water in the case of wettable powders, emulsifiable concentrates, dispersions and in some cases also microgranules. Dust-like and granular formulations as well as sprayable solutions are usually not diluted further with additional inert substances before use.

The required amount applied varies with the external conditions, such as temperature, humidity and the like. It can vary within wide limits, for example between 0.0005 and 10.0 kg/ha or more of active substance, but is preferably between 0.001 and 5 kg/ha of active compound.

The active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from these formulations as mixtures with other active compounds, such as insecticides, attractants, sterilizing agents, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.

The pesticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds and substances produced by microorganisms.

Preferred partners for the mixtures are:

1. from the group of phosphorus compounds

acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusafos (F-67825), chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, demeton, demeton-S-methyl, demeton-S-methyl sulfone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitriothion, fensulfothion, fenthion, fonofos, formothion, fosthiazate (ASC-66824), heptenophos, isazophos, isothioate, isoxathion, malathion, methacrifos, methamidophos, methidathion, salithion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosfolan, phosphocarb (BAS-301), phosmet, phosphamidon, phoxim, pirimiphos, primiphos-ethyl, pirimiphos-methyl, pro fenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinaiphos, sulprofos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, thiometon, triazophos, trichlorphon, vamidothion;

2. from the group of carbamates

alanycarb (OK-135), aldicarb, 2-sec-butylphenyl methylcarbamate (BPMC), carbaryl, carbofliran, carbosulfan, cloethocarb, benfuiracarb, ethiofencarb, furathiocarb, HCN-801, isoprocarb, methomyl, 5-methyl-m-cumenyl butyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, 1-methylthio(ethylideneamino) N-methyl-N-(morpholinothio)carbamate (UC 51717), triazamate;

3. from the group of carboxylic acid esters

acrinathrin, allethrin, alphametrin, 5-benzyl-3-furyl methyl (E)-(1R)-cis-2,2-di-methyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, beta-cyfluthrin, beta-cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), bioresmethrin, bifenthrin, (RS)-1-cyano-1-(6-phenoxy-2-pyridyl)methyl (1RS)-trans-3-(4-tert-butylphenyl)-2,2-dimethylcyclopropanecarboxylate (NCI 85193), cycloprothrin, cyfluthrin, cyhalothrin, cythithrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin (S-41311), lambda-cyhalothrin, permethrin, pheothrin ((R) isomer), prallethrin, pyrethrins (natural products), resmethrin, tefluthrin, tetramethrin, theta-cypermethrin (TD-2344), tralomethrin, transfluthrin and zeta-cypermethrin (F-56701);

4. from the group of amidines

amitraz, chlordimeform;

5. from the group of tin compounds

cyhexatin, fenbutatin oxide;

6. others

abamectin, ABG-9008, acetamiprid, Anagrapha falcitera , AKD-1022, AKD-3059, ANS-118 , Bacillus thuringiensis, Beauveria bassianea , bensultap, bifenazate (D-2341), binapacryl, BJL-932, bromopropylate, BTG-504, BTG-505, buprofezin, camphechlor, cartap, chlorobenzilate, chlorfenapyr, chlorfluazuron, 2-(4-chlorophenyl)-4,5-diphenylthiophene (UBI-T 930), chlorfentezine, chromafenozide (ANS-118), CG-216, CG-217, CG-234, A-184699, 2-naphthylmethyl cyclopropanecarboxylate (Ro 12-0470), cyromazin, diacloden (thiamethoxam), diafenthiuron, N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propyloxy)phenyl)carbamoyl)-2-chlorobenzocarboxamide acid ethyl ester, DDT, dicofol, diflubenzuron, N-(2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene)-2,4-xylidine, dinobuton, dinocap, diofenolan, DPX-062, emamectin-benzoate (MK-244), endosulfan, ethiprole (sulfethiprole), ethofenprox, etoxazole (YI-5301), fenazaquin, fenoxycarb, fipronil, fluazuron, flumite (flufenzine, SZI-121), 2-fluoro-5-(4-(4-ethoxyphenyl)-4-methyl-1-pentyl)diphenyl ether (MTI 800), granulosis and nuclear polyhedrosis viruses, fenpyroximate, fenthiocarb, flubenzimine, flucycloxuron, flufenoxuron, flufenprox (ICI-A5683), fluproxyfen, gamma-HCH, halofenozide (RH-0345), halofenprox (MTI-732), hexaflumuron (DE — 473), hexythiazox, HOI-9004, hydramethylnon (AC 217300), lufenuron, imidacloprid, indoxacarb (DPX-MP062), kanemite (AKD-2023), M-020, MTI-446, ivermectin, M-020, methoxyfenozide (Intrepid, RH-2485), milbemectin, NC-196, neemgard, nitenpyram (TI-304), 2-nitromethyl-4,5-dihydro-6H-thiazine (DS 52618), 2-nitromethyl-3,4-dihydrothiazole (SD 35651), 2-nitromethylene-1,2-thiazinan-3-ylcarbamaldehyde (WL 108477), pyriproxyfen (S-71639), NC-196, NC-1111, NNI-9768, novaluron (MCW-275), OK-9701, OK-9601, OK-9602, propargite, pymethrozine, pyridaben, pyrimidifen (SU-8801), RH-0345, RH-2485, RYI-210, S-1283, S-1833, SB7242, SI-8601, silafluofen, silomadine (CG-177), spinosad, SU-9118, tebufenozide, tebufenpyrad (MK-239), teflubenzuron, tetradifon, tetrasul, thiacloprid, thiocyclam, TI-435, tolfenpyrad (OMI-88), triazamate (RH-7988), triflumuron, verbutin, vertalec (Mykotal), YI-5301,

The abovementioned combination partners are known active compounds, and most of them are described in Ch. R. Worthing, S. B. Walker, The Pesticide Manual, 11th Edition, British Crop Protection Council Farnham 1997.

The active compound content of the use forms prepared from the commercially available formulations can be from 0.00000001 to 95% by weight of active compound, preferably between 0.00001 and 1% by weight.

The active compounds are used in a customary manner appropriate for the use forms.

The active compounds according to the invention are also suitable for controlling endo- and ectoparasites in the veterinary medicine field and in the field of animal husbandry. The active compounds according to the invention are used here in a known manner, such as by oral use in the form of, for example, tablets, capsules, potions or granules, by means of dermal use in the form of, for example, dipping, spraying, pouring-on, spotting-on and dusting, and by parenteral use in the form of, for example, injection.

The novel compounds of the formula (I′) can accordingly also particularly advantageously be used in livestock husbandry (for example cattle, sheep, pigs and poultry, such as chickens, geese and the like). In a preferred embodiment of the invention, the compounds are administered orally to the animals, if appropriate in suitable formulations and if appropriate with the drinking water or feed. Since excretion in the feces takes place in an active manner, the development of insects in the feces of the animals can be prevented very easily in this way. The dosages and formulations suitable in each case depend in particular on the species and the development stage of the stock animals and also on the level of infestation, and can easily be determined and specified by the customary methods. The compounds can be employed in cattle, for example, in dosages of 0.01 to 1 mg/kg of body weight.

In addition to the application methods mentioned hereinabove, the active compounds of the formula (I′) according to the invention also have excellent systemic action. The active compounds can therefore also be introduced into the plants via below-ground and above-ground parts of plants (root, stem, leaf), when the active compounds are applied in liquid or solid form to the immediate surroundings of the plants (for example granules in soil application, application in flooded rice fields).

Furthermore, the active compounds according to the invention are particularly useful for treating vegetative and generatative propagation stock, such as, for example, seed of, for example, cereals, vegetables, cotton, rice, sugar beet and other crops and ornamentals, of bulbs, cuttings and tubers of other vegetatively propagated crops and ornamentals. To this end, treatment can be carried out prior to sowing or planting (for example by special seed coating techniques, by seed dressings in liquid or solid form or by seed box treatment), during sowing or planting or after sowing or planting by special application techniques (for example seed row treatment). Depending on the application, the amount of active compound applied can vary within a relatively wide range. In general, the application rates are between 1 g and 10 kg of active compound per hectare of soil area.

The compounds of the formula (I′) can also be used for controlling harmful plants in crops of known genetically modified plants or of genetically modified plants still to be developed. The transgenic plants generally have particularly advantageous properties, for example resistance to certain crop protection agents, resistance to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms, such as fungi, bacteria or viruses. Other special properties relate, for example, to the harvested product, with respect to quantity, quality, shelf-life, composition and special ingredients. Thus, transgenic plants having increased starch content or a modified quality of the starch or those having a different fatty acid composition of the harvested product are known.

Preference is given to the use in economically important transgenic crops of useful and ornamental plants, for example cereals, such as wheat, barley, rye, oats, millet, rice, manioc and maize, or else crops of sugar beet, cotton, soya, rapeseed, potato, tomato, pea and other vegetable species.

The use in transgenic crops, in particular crops with resistance to insects, is, in addition to the effects with respect to harmful organisms which can be observed in other crops, frequently associated with effects which are specific for the application in the respective transgenic crop, for example a modified or specifically widened spectrum of pests which can be controlled, or modified application rates which can be used for the application.

The invention therefore also provides the use of compounds of the formula (I′) for controlling harmful organisms in transgenic crop plants.

The use of the compounds according to the invention comprises, in addition to direct application to the pests, any other application where the compounds of the formula (I′) act on the pests. Such indirect applications may be, for example, the use of compounds which decompose or are degraded to compounds of the formula (I′), for example in the soil, the plant or the pest.

Herewith, express reference is made to the content of German Patent Application 198 581 93.9, the priority of which is claimed by the present application, and to the content of the enclosed summary; they are incorporated into this description by reference.

The examples below serve to illustrate the invention.

EXAMPLES

I. COMPOUNDS OF FORMULA (I)

A. Formulation Examples

a) A dusting powder is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc, as the inert substance, and comminuting the mixture in an impact mill.

b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of active compound, 65 parts by weight of kaolin-containing quartz, as the inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltauride, as wetting and dispersing agent and grinding the mixture in a pinned disk mill.

c) A dispersion concentrate which is readily dispersible in water is prepared by mixing 40 parts by weight of active compound with 7 parts by weight of a sulfosuccinic monoester, 2 parts by weight of a sodium ligninsulfonate and 51 parts by weight of water and grinding the mixture to a fineness of below 5 microns in a grinding bead mill.

d) An emulsifiable concentrate can be prepared from 15 parts by weight of active compound, 75 parts by weight of cyclohexane, as the solvent, and 10 parts by weight of ethoxylated nonylphenol (10 EO), as the emulsifier.

e) Granules can be prepared from 2 to 15 parts by weight of active compound and an inert granule carrier material, such as attapulgite, pumice granules and/or quartz sand. A suspension of the wettable powder from Example b) having a solids content of 30% is expediently used, and this is sprayed onto the surface of attapulgite granules and the components are dried and mixed intimately. The weight content of the wettable powder is approximately 5% and that of the inert carrier material is approximately 95% of the finished granules.

B. Chemical Examples

Example No. 1

3-Isopropyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole (Table 1, No. 81)

2 g of methyl 4-trifluoromethylnicotinate and 1.56 g of isobutyramide oxime were initially charged in 15 ml of ethanol and cooled to 0° C. 10 ml of a 1.2 molar sodium ethoxide solution were added dropwise to this solution. The mixture was allowed to warm to room temperature over a period of two hours and stirring was then continued at this temperature until the reaction, according to TLC, had ended.

The reaction mixture was concentrated and the residue was taken up in saturated ammonium chloride solution and extracted with diethyl ether. Chromatographic purification of the crude product gave the desired compound as a yellowish oil.

1 H-NMR (CDCl 3 , 300 MHz): d=1.41 (d, J=6.9 Hz, 6H), 3.22 (m, 1H), 7.78 (d, J=5 Hz, 1H), 9.02 (d, J=5 Hz, 1H), 9.34 (s, 1H) ppm.

Example No. 2

3-Isopropyl-5-(4-trifluoromethyl-5-pyrimidyl)-1,2,4-oxadiazole (Table 1, No. 189)

2 g of ethyl 4-trifluoromethylpyrimidine-5-carboxylate and 1.56 g of isobutyramide oxime were initially charged in 15 ml of ethanol and cooled to 0° C. 10 ml of a 1.2 molar sodium ethoxide solution were added dropwise to this solution. The mixture was allowed to warm to room temperature over a period of one hour and then heated under reflux until the reaction, according to TLC, had ended. The reaction mixture was concentrated and the residue was taken up in saturated ammonium chloride solution and extracted with diethyl ether. Chromatographic purification of the crude product gave the desired compound as a yellowish oil.

1 H-NMR (CDCl 3 , 300 MHz): d=1.43 (d, J=7 Hz, 6H), 3.22 (hept., J=7 Hz, 1H), 9.52 (s, 1H), 9.58 (s, 1H) ppm.

Example No. 3

2-Methyl-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole (Table 3, No. 549)

500 mg of 4-trifluoromethylnicotinic hydrazide were heated under reflux in 3.5 ml of triethyl orthoacetate for 2 hours. The reaction mixture was subsequently concentrated and the residue was carefully admixed with 2 ml of phosphorus oxychloride. The mixture was stirred at room temperature for 1 hour and then poured on ice and extracted with ethyl acetate. Chromatographic purification of the crude product obtained after drying and concentrating gave the desired compound as a yellowish oil.

1 H-NMR (CDCl 3 , 300 MHz): d=2.67 (s, 3H), 7.75 (d, J=5 Hz, 1H), 8.99 (d, J=5 Hz, 1H), 9.34 (s, 1H) ppm.

Example No. 4

4-(Ethoxycarbonylmethyl)-2-(4-trifluoromethyl-3-pyridyl)thiazole (Table 4, No. 688)

500 mg of 4-trifluoromethylpyridine-3-thiocarboxamide and 440 mg of ethyl 4-chloroacetate were dissolved in 5 ml of dimethylformamide and heated at 100° C. for 4 hours. After cooling, the reaction mixture was poured onto ice-water and extracted with diethyl ether. The diethyl ether phase was dried (MgSO 4 ), filtered and concentrated and the residue was purified by chromatography. This gave the desired product in pure form as a colorless oil.

1 H-NMR (CDCl 3 , 300 MHz): d=1.28 (t, J=7.5 Hz, 3H), 3.92 (s, 2H), 4.22 (q, J=7.5 Hz, 2H), 7.43 (s, 1H), 7.68 (d, J=5 Hz, 1H), 8.86 (d, J=5 Hz, 1H), 8.97 (s, 1H) ppm.

Example No. 5

4-Ethyl-2-(4-trifluoromethyl-3-pyridyl)oxazole (Table 4, No. 762)

2.6 g of 4-trifluoromethylnicotinic acid were admixed with 20 ml of thionyl chloride and heated at reflux temperature for 1 hour. After cooling, excess thionyl chloride was distilled off and the acyl chloride which remained as a pale yellow oil was taken up in 30 ml of dichloromethane. This solution was subsequently added dropwise to a solution of 2.4 g of 2-amino-1-butanol and 2.75 g of triethylamine in 30 ml of dichloromethane cooled in an ice bath. After the addition had ended, stirring was continued at room temperature for approximately 2 hours. The mixture was poured into ammonium chloride solution and extracted with ethyl acetate. The crude N-(1-hydroxy-2-butyl)-4-trifluoromethylnicotinamide (2.3 g) obtained after drying and concentrating the ethyl acetate phase was dissolved at room temperature in 100 ml dichloromethane and mixed with 4.6 g of periodinan (Dess-Martin reagent). After the reaction had ended, according to TLC, the reaction mixture was concentrated and purified by column chromatography. The resulting 2-(trifluoromethylpyridin-3-amido)butanal (1.5 g) was dissolved in 30 ml of dimethylformamide, admixed with 2.72 g of phosphorus oxychloride and heated at 90° C. for 15 minutes. The solution was then poured onto ice and extracted with diethyl ether. Drying and concentration of the diethyl ether phase and chromatographic purification of the residue gave the product as a brownish oil.

1 H-NMR (CDCl 3 , 300 MHz): d=1.3 (t, J=7.4 Hz, 3H), 2.66 (qd, J=7.4 Hz, J<1 Hz, 2H), 7.58 (t, J<1 Hz, 1H), 7.65 (d, J=5 Hz, 1H), 8.83 (d, J=5 Hz, 1H), 9.33 (d, J=5 Hz, 1H) ppm.

Example No. 6

4-Ethyl-2-(4-trifluoromethyl-3-pyridyl)-4,5-dihydrooxazole (Table 5, No 876)

1 g of 4-trifluoromethylnicotinic acid was admixed with 8 ml of thionyl chloride and heated at reflux temperature for 1 hour. After cooling, excess thionyl chloride was distilled off and the acyl chloride which remained as a pale yellow oil was taken up in 10 ml of dichloromethane. This solution was subsequently added dropwise to a solution of 930 mg of 2-amino-1-butanol and 1.06 g of triethylamine in 10 ml of dichloromethane cooled in an ice bath. After the addition had ended, stirring was continued for approximately 2 hours at room temperature. The mixture was poured into an ammonium chloride solution and extracted with ethyl acetate. The crude N-(1-hydroxy-2-butyl)-4-trifluoromethylnicotinamide (1.03 g) obtained after drying and concentration of the ethyl acetate phase was dissolved at room temperature in 6 ml of tetrahydrofuran and admixed with 1.09 g of N-[(triethylammonio)sulfonyl]-methylcarbamate (Burgess' reagent). The mixture was stirred at 60° C. for 3 hours. After cooling, the batch was concentrated and the residue was taken up in water and extracted with ethyl acetate. Chromatographic purification of the crude product gave the product as a colorless oil.

1 H-NMR (CDCl 3 , 200 MHz): d=1.03 (t, J=7.6 Hz, 3H), 1.72 (m, 2H), 4.15 (t, J=7.5 Hz, 1H), 4.32 (m, 1H), 4.58 (t, J=7.5 Hz, 1H), 7.6 (d, J=5 Hz, 1H), 8.87 (d, J=5 Hz, 1H), 9.06 (s, 1H) ppm.

Example No. 7

2-(3-Thienylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole (Table 3, No. 572)

880 mg of thiophene-3-acetic hydrazide were added to a solution of 960 mg of 4-trifluoromethylpyridine-3-carboxylic acid in 5 ml of phosphorus oxychloride, and the mixture was heated at reflux for 2 hours. The reaction mixture was subsequently added dropwise to ice-water, made neutral using concentrated ammonia solution and extracted with ethyl acetate. Drying (Na 2 SO 4 ), concentration and chromatographic purification gave 624 mg of the desired product as a slightly brown oil.

1 H-NMR (CDCl 3 , 200 MHz): d=4.38 (s, 2H), 7.1 (d, J=5 Hz, 1H), 7.23 (s, 1H), 7.37 (dd, J=5 Hz, J=3 Hz, 1H), 7.75 (d, J=6 Hz, 1H), 8.98 (d, J=6 Hz, 1H), 9.36 (s, 1H) ppm.

Example No. 8

5-Methyl-3-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole (Table 6, No. 947)

A mixture of 290 mg of ethylacetimidate hydrochloride and 100 mg of sodium hydroxide in 2 ml of ethanol was filtered and added to 500 mg of 4-trifluoromethyl-3-pyridinecarbohydrazide, and the mixture was heated under reflux for 3 hours. The reaction mixture was concentrated and the residue was suspended in xylene and refluxed for 4 hours. For work-up, the batch was diluted with ethyl acetate and washed with water. Chromatographic purification gave the pure product as a colorless solid.

1 H-NMR (CDCl 3 , 300 MHz): d=2.58 (s, 3H), 7.64 (d, J=5 Hz, 1H), 8.85 (d, J=5 Hz, 1H), 9.19 (s, 1H) ppm.

Example No. 9

3-(N-Isopropylcarbamoylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

Step 1: Tert-butyl 3-Amino-3-(4-trifluoromethyl-3-pyridinecarbonyloxy-imino)propionate

30 g of 4-trifluoromethyl-3-pyridinecarboxylic acid is initially charged in 150 ml of dry THF and, a little at a time, admixed with 25.3 g of carbonyl-diimidazole. The mixture is stirred at room temperature for 30 min. 27.2 g of tert-butoxycarbonylacetamide oxime dissolved in 150 ml of THF are then added dropwise. The mixture is stirred overnight, the solvent is evaporated and the residue is taken up in ethyl acetate, washed three times with 1 M sulfuric acid and once with saturated sodium bicarbonate solution. Concentration of the ethyl acetate phase gives 28 g of the product as a pale yellow solid.

1 H-NMR (CDCl 3 , 300MHz): d=1.5 (s, 9H), 3.3 (s, 2H), 5.55 (br.s, 2H), 7.83 (d, J=5 Hz, 1H), 8.97 (d, J=5 Hz, 1H), 9.13 (s, 1H) ppm.

Step 2: 3-(Tert-butoxycarbonylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

28 g of tert-butyl 3-amino-3-(4-trifluoromethyl-3-pyridinecarbonyloxy-imino)propionate are dissolved in 380 ml of toluene and heated under reflux for 17 hours. Concentration and chromatographic purification of the residue over silica gel gives 14.4 g of the product as a pale brown oil.

1 H-NMR (CDCl 3 , 300MHz): d=1.5 (s, 9H), 3.88 (s, 2H), 7.79 (d, J=5 Hz, 1H), 9.02 (d, J=5 Hz, 1H), 9.33 (s, 1H) ppm.

Step 3: 3-(Hydroxycarbonylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

12.4 g of 3-(tert-butoxycarbonylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole are dissolved in 110 ml of dichloromethane and admixed with 57 ml of trifluoroacetic acid. The reaction mixture is stirred at room temperature for 1.5 hours and subsequently concentrated under reduced pressure. The residue is repeatedly taken up in dichloromethane and reconcentrated to remove any remaining trifluoroacetic acid. The mixture is finally triturated with diethyl ether, giving 8.1 g of the product as a white solid.

Step 4: 3-(N-Isopropylcarbamoylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

1 g of the product of the previous step are dissolved in 10 ml of THF and is mixed with 0.59 g of carbonyldiimidazole. The mixture is stirred at room temperature for 10 minutes, 0.22 g of isopropylamine are added dropwise and the mixture is allowed to react for a further 1.5 hours at room temperature with stirring. The reaction mixture is subsequently concentrated and the residue is taken up in ethyl acetate and washed three times with 1 M sulfuric acid and once with saturated sodium bicarbonate solution. The solid residue obtained after drying and concentrating the ethyl acetate phase is recrystallized from tert-butyl methyl ether, giving 0.46 g of the pure product as a pale yellow solid.

1 H-NMR (CDCl 3 , 300MHz): d=1.20 (d, J=7.6 Hz, 6H), 3.82 (s, 2H), 4.12 (m, 1H), 6.50 (br.s, 1H), 7.81 (d, J=5 Hz, 1H), 9.02 (d, J=5 Hz, 1H), 9.37 (s, 1H) ppm.

Example No. 10

3-(N,N-Dimethylaminocarbamoyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole (Table 1, No. 502)

Step 1: Ethyl 2-Amino-2-(4-trifluoromethyl-3-pyridinecarbonyloxyimino)acetate

17.3 g of carbonyldiimidazole are initially charged in 200 ml of 1,4-dioxane and, a little at a time, admixed with 20 g of 4-trifluoromethyl-3-pyridinecarboxylic acid. The mixture is stirred at room temperature for 1 h and subsequently heated to 45° C. for 2 h. After cooling to 30° C., 14.5 g of ethoxycarbonylformamide oxime are added and the mixture is stirred at 45° C. for 3 h. The precipitated solid is filtered off with suction and the filtrate is concentrated to 50 ml and, together with the solid, added to 250 ml of ice-water. The solid is filtered off with suction and dried at 50° C. under reduced pressure. This gives 28.7 g of the product as a white solid of mp. 172-174° C.

Step 2: 3-Ethoxycarbonyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

20 g of ethyl 2-amino-2-(4-trifluormethyl-3-pyridinecarbonyloxyimino)-acetate are dissolved in 200 ml of a mixture of xylene and toluene and admixed with 5 g of Amberlyst 15. The mixture is boiled at 125-130° C. for 6 h using a Dean-Stark apparatus. After the reaction has ended, the mixture is cooled and admixed with a small amount of diethyl ether. The mixture is filtered with suction through a glass filter frit, and the solution is then concentrated. This gives 15.8 g of the product as a yellow oil.

Step 3: 5-(4-Trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxylic Acid

15.8 g of 3-ethoxycarbonyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole are initially charged in 13 ml of methanol, and, with ice-cooling at 0° C., a solution of 2.8 g of lithium hydroxide in 50 ml of water is added dropwise. The mixture is stirred at room temperature for 2 h, 20 ml of ice-water are added and the mixture is extracted with 200 ml of diethyl ether. The aqueous phase is adjused to pH=2 using dil. HCl, and the precipitated product is filtered off with suction. After drying, 13.8 g of 5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxylic acid are obtained as a white solid of mp. 157-159° C.

Step 4: N,N-Dimethyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxamide

5.8 g of carbonyldiimidazole are initially charged in 90 ml of tetrahydrofuran and, a little at a time, admixed with 9 g of 5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxylic acid. The mixture is stirred at room temperature for 15 min and then heated at 50° C. for 2 h. After cooling to room temperature, 2.3 g of dimethylamine are introduced in a very gentle gas stream over a period of 2 h. After a reaction time of 12 h, the mixture is concentrated and taken up in 200 ml of diethyl ether. The mixture is washed with ice-cold half conc. hydrochloric acid solution, washed neutral with sat. sodium bicarbonate sol., dried over magnesium sulfate and concentrated under reduced pressure. This gives a slightly yellow oil which solidifies after a number of days to a solid of mp. 52-54° C.

In a similar manner, it is possible to prepare the compounds shown in Tables 1 to 6 below. The abbreviations used denote Ph: phenyl THP: 2-tetrahydropyranyl

TABLE 1
No.	X	Y	m	W	R 1	m.p. [° C.]
1	N	CCl 3	0	O	CH 3
2	N	CCl 3	0	O	CH 2 CH 3
3	N	CCl 3	0	O	COOCH 2 CH 3
4	CH	CCl 3	0	O	CH 3
5	CH	CCl 3	0	O	COOCH 2 CH 3
6	N	(CF 2 ) 3 CHCF 2	0	O	CH 3
7	N	(CF 2 ) 3 CHCF 2	0	O	COOCH 2 CH 3
8	CH	(CF 2 ) 3 CHCF 2	0	O	CH 3
9	CH	(CF 2 ) 3 CHCF 2	0	O	COOCH 2 CH 3
10	N	(CF 2 ) 3 CHCF 2	0	S	CH 2 COOC(CH 3 ) 3
11	N	(CF 2 ) 3 CHCF 2	0	S	CH 2 CONHCH 3
12	CH	(CF 2 ) 3 CHCF 2	0	S	(CH 2 ) 2 CH 3
13	CH	(CF 2 ) 3 CHCF 2	0	S	COOCH 2 CH 3
14	N	(CF 2 ) 2 CHCF 2	0	O	CH 2 CH 3
15	N	(CF 2 ) 2 CHCF 2	0	O	COOCH 2 CH 3
16	N	(CF 2 ) 2 CHCF 2	0	O	OH
17	N	(CF 2 ) 2 CHCF 2	0	O	OCH 3
18	CH	(CF 2 ) 2 CHCF 2	0	O	CH 3
19	CH	(CF 2 ) 2 CHCF 2	0	O	COOCH 2 CH 3
20	CH	(CF 2 ) 2 CHCF 2	0	O	OH
21	CH	(CF 2 ) 2 CHCF 2	0	O	NHCH 3
22	N	CF 2 CF 3	0	O	CH 3
23	N	CF 2 CF 3	0	O	CH 2 CH 3
24	N	CF 2 CF 3	0	O	(CH 2 ) 2 CH 3
25	N	CF 2 CF 3	0	O	CH(CH 3 ) 2
26	N	CF 2 CF 3	0	O	Cyclo-C 6 H 11
27	N	CF 2 CF 3	0	O	CH 2 C═CH 2
28	N	CF 2 CF 3	0	O	CH 2 C≡CH
29	N	CF 2 CF 3	0	O	CH 2 CH 2 C≡CH
30	N	CF 2 CF 3	0	O	CH 2 C≡CCH 2 CH 3
31	N	CF 2 CF 3	0	O	(CH 2 ) 4 C≡CH
32	N	CF 2 CF 3	0	O	CHFCF 3
33	N	CF 2 CF 3	0	O	COOCH 2 CH 3
34	N	CF 2 CF 3	0	O	CH 2 COOC(CH 3 ) 3
35	N	CF 2 CF 3	0	O	CH 2 CONHCH 3
36	N	CF 2 CF 3	0	O	NH 2
37	N	CF 2 CF 3	0	O	NHCH 2 CH 3
38	CH	CF 2 CF 3	0	O	CH 3
39	CH	CF 2 CF 3	0	O	CH 2 CH 3
40	CH	CF 2 CF 3	0	O	(CH 2 ) 2 CH 3
41	CH	CF 2 CF 3	0	O	CH(CH 3 ) 2
42	CH	CF 2 CF 3	0	O	Cyclo-C 6 H 11
43	CH	CF 2 CF 3	0	O	CH 2 C═CH 2
44	CH	CF 2 CF 3	0	O	CH 2 COOC(CH 3 ) 3
45	CH	CF 2 CF 3	0	O	NH 2
46	CH	CF 2 CF 3	0	O	NHCOCH 3
47	CH	CF 2 CF 3	0	O	NHCOCH 2 CH 3
48	N	CF 2 CF 3	0	S	CH 3
49	N	CF 2 CF 3	0	S	CH 2 CH 3
50	N	CF 2 CF 3	0	S	(CH 2 ) 2 CH 3
51	N	CF 2 Cl	0	O	CH 3
52	N	CF 2 Cl	0	O	CH 2 CH 3
53	N	CF 2 Cl	0	O	(CH 2 ) 2 CH 3
54	N	CF 2 Cl	0	O	CH(CH 3 ) 2
55	N	CF 2 Cl	0	O	CH 2 COOC(CH 3 ) 3
56	N	CF 2 Cl	0	O	CH 2 CONHCH 3
57	N	CF 2 Cl	0	O	OH
58	N	CF 2 Cl	0	O	OCH 3
59	N	CF 2 Cl	0	O	OCH 2 CH 3
60	N	CF 2 Cl	0	O	NHCH 3
61	CH	CF 2 Cl	0	O	CH 3
62	CH	CF 2 Cl	0	O	CH 2 CH 3
63	CH	CF 2 Cl	0	O	(CH 2 ) 2 CH 3
64	CH	CF 2 Cl	0	O	CH(CH 3 ) 2
65	CH	CF 2 Cl	0	O	CH 2 COOC(CH 3 ) 3
66	CH	CF 2 Cl	0	O	CH 2 CONHCH 3
67	CH	CF 2 Cl	0	O	OH
68	CH	CF 2 Cl	0	O	OCH 3
69	CH	CF 2 Cl	0	O	OCH 2 CH 3
70	CH	CF 2 Cl	0	O	NHCH 3
71	CH	CF 2 Cl	0	O	Cyclo-C 6 H 11
72	CH	CF 2 Cl	0	O	CH 2 C═CH 2
73	CH	CF 2 Cl	0	O	COOCH 2 CH 3
74	CH	CF 2 Cl	0	O	CH 2 COOC(CH 3 ) 3
75	CH	CF 2 Cl	0	O	CH 2 CONHCH 3
76	CH	CF 2 Cl	0	O	OCH 3
77	CH	CF 2 Cl	0	O	NHCH 3
78	CH	CF 3	0	O	CH 3	oil
79	CH	CF 3	0	O	CH 2 CH 3	oil
80	CH	CF 3	0	O	(CH 2 ) 2 CH 3	oil
81	CH	CF 3	0	O	CH(CH 3 ) 2	oil
82	CH	CF 3	0	O	Cyclo-C 3 H 5	oil
83	CH	CF 3	0	O	(CH 2 ) 3 CH 3	oil
84	CH	CF 3	0	O	CH(CH 3 )CH 2 CH 3	oil
85	CH	CF 3	0	O	CH 2 CH(CH 3 ) 2	oil
86	CH	CF 3	0	O	C(CH 3 ) 3	oil
87	CH	CF 3	0	O	Cyclo-C 4 H 7
88	CH	CF 3	0	O	(CH 2 ) 4 CH 3	oil
89	CH	CF 3	0	O	CH(CH 3 )(CH 2 ) 2 CH 3
90	CH	CF 3	0	O	(CH 2 ) 2 CH(CH 3 ) 2
91	CH	CF 3	0	O	CH 2 C(CH 3 ) 3
92	CH	CF 3	0	O	Cyclo-C 5 H 9	oil
93	CH	CF 3	0	O	(CH 2 ) 5 CH 3
94	CH	CF 3	0	O	C(CH 2 CH 3 ) 2 CH 3
95	CH	CF 3	0	O	Cyclo-C 6 H 11
96	CH	CF 3	0	O	(CH 2 ) 6 CH 3
97	CH	CF 3	0	O	CH(CH 3 )(CH 2 ) 4 CH 3
98	CH	CF 3	0	O	Cyclo-C 7 H 13
99	CH	CF 3	0	O	CH 2 -cyclo-C 6 H 11
100	CH	CF 3	0	O	2-Norbornyl
101	CH	CF 3	0	O	(CH 2 ) 7 CH 3
102	CH	CF 3	0	O	CH(CH 2 CH 3 )(CH 2 ) 5 CH 3
103	CH	CF 3	0	O	(CH 2 ) 8 CH 3
104	CH	CF 3	0	O	(CH 2 ) 3 -cyclo-C 6 H 11
105	CH	CF 3	0	O	(CH 2 ) 9 CH 3
106	CH	CF 3	0	O	1-Adamantyl
107	CH	CF 3	0	O	(CH 2 ) 10 CH 3
108	CH	CF 3	0	O	(CH 2 ) 11 CH 3
109	CH	CF 3	0	O	CH(CH 3 )(CH 2 ) 9 CH 3
110	CH	CF 3	0	O	(CH 2 ) 12 CH 3
111	CH	CF 3	0	O	(CH 2 ) 13 CH 3
112	CH	CF 3	0	O	(CH 2 ) 14 CH 3
113	CH	CF 3	0	O	(CH 2 ) 15 CH 3
114	CH	CF 3	0	O	(CH 2 ) 17 CH 3
115	CH	CF 3	0	O	(CH 2 ) 19 CH 3
116	CH	CF 3	0	O	CHO
117	CH	CF 3	0	O	CH═CH 2	oil
118	CH	CF 3	0	O	CH 2 C═C(CH 3 ) 2
119	CH	CF 3	0	O	CH 2 CH 2 C═CH 2
120	CH	CF 3	0	O	CH 2 C═CH 2
121	CH	CF 3	0	O	C(CH 3 )═CH 2
122	CH	CF 3	0	O	(E)-CH 2 CH═CHCH 2 CH 3
123	CH	CF 3	0	O	(Z)-CH 2 CH═CHCH 2 CH 3
124	CH	CF 3	0	O	(CH 2 ) 5 C═CH 2
125	CH	CF 3	0	O	C(═CHCH 3 )CH 3	62-64
126	CH	CF 3	0	O	Geranyl
127	CH	CF 3	0	O	3-Menthyl
128	CH	CF 3	0	O	C≡CH
129	CH	CF 3	0	O	CH 2 C≡CH
130	CH	CF 3	0	O	CH 2 CH 2 C≡CH
131	CH	CF 3	0	O	CH 2 CH 2 C≡CH
132	CH	CF 3	0	O	(CH 2 ) 4 C≡CH
133	CH	CF 3	0	O	CHFCF 3	oil
134	CH	CF 3	0	O	COOCH 2 CH 3	oil
135	CH	CF 3	0	O	CH 2 CH 2 OH	oil
136	CH	CF 3	0	O	CH 2 CH 2 OCH 3	oil
137	CH	CF 3	0	O	CH 2 COOC(CH 3 ) 3	oil
138	CH	CF 3	0	O	CH 2 SC 6 H 5	oil
139	CH	CF 3	0	O	CH 2 CONHCH 3	109-111
140	CH	CF 3	0	O	CH 2 CH(OH)CH 2 OH
141	CH	CF 3	0	O	CH 2 COCH 3
142	CH	CF 3	0	O	COCH3
143	CH	CF 3	0	O	CH 2 OC 6 H 5
144	CH	CF 3	0	O	COC 6 H 5
145	CH	CF 3	0	O	CO(4-Cl)—C 6 H 4
146	CH	CF 3	0	O	CF 2 CH 3
147	CH	CF 3	0	O	CH 2 CN
148	CH	CF 3	0	O	CH 2 CH 2 CN
149	CH	CF 3	0	O	CH 2 CH(—O—)CH 2
150	CH	CF 3	0	O	CH 2 (4-OCH 3 )C 6 H 5
151	CH	CF 3	0	O	CH 2 -cyclo-(4-Oxo)-C 6 H 8
152	CH	CF 3	0	O	CH 2 CH(OH)CH 2 SC 6 H 5
153	CH	CF 3	0	O	CH 2 CH 2 Si(CH 3 ) 3
154	CH	CF 3	0	O	CH═CF 2
155	CH	CF 3	0	O	CCl═CHCl
156	CH	CF 3	0	O	2-Pyridyl	99-101
157	CH	CF 3	0	O	2-Furyl
158	CH	CF 3	0	O	2-Thienyl	106-108
159	CH	CF 3	0	O	CH 2 C≡CCH 2 CH 2 OTHP
160	CH	CF 3	0	O	CH 2 CH 2 CI	oil
161	CH	CF 3	0	O	Si(CH 3 ) 3
162	CH	CF 3	0	O	OC 6 H 5
163	CH	CF 3	0	O	OH
164	CH	CF 3	0	O	OCH 3
165	CH	CF 3	0	O	OCH 2 CH 3
166	CH	CF 3	0	O	OCHF 2
167	CH	CF 3	0	O	OCH 2 C 6 H 5
168	CH	CF 3	0	O	CH 2 SCH 3	48-49
169	CH	CF 3	0	O	SC 6 H 5
170	CH	CF 3	0	O	SeC 6 H 5
171	CH	CF 3	0	O	NH 2	116-118
172	CH	CF 3	0	O	NHCH 3
173	CH	CF 3	0	O	NHCH 2 CH 3
174	CH	CF 3	0	O	N(CH 2 CH 3 ) 2
175	CH	CF 3	0	O	CONHCH 2 C═CH 2	105-107
176	CH	CF 3	0	O	Cl
177	CH	CF 3	0	O	Br
178	CH	CF 3	0	O	CONH 2	206-208
179	CH	CF 3	0	O	NHCOCH 3	129-131
180	CH	CF 3	0	O	NHCOCH 2 CH 3
181	CH	CF 3	0	O	OSO 2 CH 3
182	CH	CF 3	0	O	SOCH 2 (4-Br)—C 6 H 4
183	CH	CF 3	0	O	N(CH 3 )COOCH 2 C 6 H 5
184	CH	CF 3	0	O	NHNH 2
185	CH	CF 3	0	O	NHN(CH 3 ) 2
186	N	CF 3	0	O	CH 3
187	N	CF 3	0	O	CH 2 CH 3	oil
188	N	CF 3	0	O	(CH 2 ) 2 CH 3	oil
189	N	CF 3	0	O	CH(CH 3 ) 2	oil
190	N	CF 3	0	O	(CH 2 ) 3 CH 3	oil
191	N	CF 3	0	O	CH 2 CH(CH 3 ) 2	oil
192	N	CF 3	0	O	C(CH 3 ) 3
193	N	CF 3	0	O	(CH 2 ) 4 CH 3	oil
194	N	CF 3	0	O	CH(CH 3 )(CH 2 ) 2 CH 3
195	N	CF 3	0	O	CH 2 C(CH 3 ) 3
196	N	CF 3	0	O	Cyclo-C 5 H 9
197	N	CF 3	0	O	(CH 2 ) 5 CH 3
198	N	CF 3	0	O	Cyclo-C 6 H 11
199	N	CF 3	0	O	CH(CH 3 )(CH 2 ) 4 CH 3
200	N	CF 3	0	O	CH 2 -cyclo-C 6 H 11
201	N	CF 3	0	O	(CH 2 ) 7 CH 3
202	N	CF 3	0	O	(CH 2 ) 8 CH 3
203	N	CF 3	0	O	(CH 2 ) 9 CH 3
204	N	CF 3	0	O	CH(CH 3 )(CH 2 ) 9 CH 3
205	N	CF 3	0	O	(CH 2 ) 15 CH 3
206	N	CF 3	0	O	(CH 2 ) 17 CH 3
207	N	CF 3	0	O	(CH 2 ) 19 CH 3
208	N	CF 3	0	O	CH 2 CH═C(CH 3 ) 2
209	N	CF 3	0	O	CH 2 CH 2 CH═CH 2
210	N	CF 3	0	O	CH 2 CH═CH 2
211	N	CF 3	0	O	(Z)-CH 2 CH═CHCH 2 CH 3
212	N	CF 3	0	O	(CH 2 ) 5 CH═CH 2
213	N	CF 3	0	O	CH 2 C≡CH
214	N	CF 3	0	O	CH 2 C≡CCH 2 CH 3
215	N	CF 3	0	O	CHFCF 3
216	N	CF 3	0	O	COOCH 2 CH 3
217	N	CF 3	0	O	CH 2 CH 2 OH
218	N	CF 3	0	O	CH 2 CH 2 OCH 3
219	N	CF 3	0	O	CH 2 COOC(CH 3 ) 3
220	N	CF 3	0	O	CH 2 SC 6 H 5
221	N	CF 3	0	O	CH 2 CONHCH 3
222	N	CF 3	0	O	CH 2 CH(OH)CH 2 OH
223	N	CF 3	0	O	CHO
224	N	CF 3	0	O	COCH 3
225	N	CF 3	0	O	CH 2 OC 6 H 5
226	N	CF 3	0	O	COC 6 H 5
227	N	CF 3	0	O	CF 2 CH 3
228	N	CF 3	0	O	CH 2 CN
229	N	CF 3	0	O	CH 2 CH 2 CN
230	N	CF 3	0	O	CH═CF 2
231	N	CF 3	0	O	2-Furyl
232	N	CF 3	0	O	CH 2 C≡C—I
233	N	CF 3	0	O	OH
234	N	CF 3	0	O	OCH 3
235	N	CF 3	0	O	OCH 2 CH 3
236	N	CF 3	0	O	OCHF 2
237	N	CF 3	0	O	OCH 2 C 6 H 5
238	N	CF 3	0	O	SC 6 H 5
239	N	CF 3	0	O	NH 2
240	N	CF 3	0	O	NHCH 3
241	N	CF 3	0	O	NHCH 2 CH 3
242	N	CF 3	0	O	N(CH 2 CH 3 ) 2
243	N	CF 3	0	O	N(CH 2 CN) 2
244	N	CF 3	0	O	N(CH 3 ) 2
245	N	CF 3	0	O	NHCOCH 3
246	N	CF 3	0	O	NHCOCH 2 CH 3
247	N	CF 3	0	O	OSO 2 CH 3
248	N	CF 3	0	O	NHNH 2
249	CH	CF 3	0	S	CH 3
250	CH	CF 3	0	S	CH 2 CH 3
251	CH	CF 3	0	S	(CH 2 ) 2 CH 3
252	CH	CF 3	0	S	CHO
253	CH	CF 3	0	S	CHFCF 3
254	CH	CF 3	0	S	CH 2 C≡CH
255	CH	CF 3	0	S	COOCH 2 CH 3
256	CH	CF 3	0	S	CH 2 COOC(CH 3 ) 3
257	CH	CF 3	0	S	CH 2 CN
258	CH	CF 3	0	S	SeC 6 H 5
259	N	CF 3	0	S	CH 3
260	N	CF 3	0	S	CH 2 CH 3
261	N	CF 3	0	S	(CH 2 ) 2 CH 3
262	N	CF 3	0	S	CHFCF 3
263	N	CF 3	0	S	CH 2 CH 2 OH
264	N	CF 3	0	S	CH 2 COOC(CH 3 ) 3
265	CH	CH 2 CH 2 Cl	0	O	CH 3
266	CH	CH 2 CH 2 Cl	0	O	CH 2 CH 3
267	CH	CH 2 CH 2 Cl	0	O	(CH 2 ) 2 CH 3
268	CH	CH 2 CH 2 Cl	0	O	CH(CH 3 ) 2
269	CH	CH 2 CH 2 Cl	0	O	CH 2 SC 6 H 5
270	CH	CH 2 CH 2 Cl	0	O	CH 2 CONHCH 3
271	CH	CH 2 CH 2 Cl	0	O	NH 2
272	CH	CH 2 CH 2 Cl	0	O	NHCH 2 CH 3
273	N	CH 2 CH 2 Cl	0	O	CH 2 CH 3
274	N	CH 2 CH 2 Cl	0	O	NH 2
275	N	CH 2 Cl	0	O	CH 3
276	CH	CH 2 Cl	0	O	CH 3
277	CH	CHF 2	0	O	CH 3
278	CH	CHF 2	0	O	CH 2 CH 3
279	CH	CHF 2	0	O	(CH 2 ) 2 CH 3
280	CH	CHF 2	0	O	CH 2 CH═CH 2
281	CH	CHF 2	0	O	C(CH 3 )═CH 2
282	CH	CHF 2	0	O	COOCH 2 CH 3
283	CH	CHF 2	0	O	CH 2 CONHCH 3
284	CH	CHF 2	0	O	CF 2 CH 3
285	CH	CHF 2	0	O	CHO
286	CH	CHF 2	0	O	NH 2
287	CH	CHF 2	0	O	Cl
288	CH	CHF 2	0	O	NHCOCH 3
289	CH	CHF 2	0	O	NHNH 2
290	N	CHF 2	0	O	CH 3
291	N	CHF 2	0	O	CH 2 CH 3
292	N	CHF 2	0	O	CH(CH 3 )(CH 2 ) 4 CH 3
293	N	CHF 2	0	O	CH 2 CH═CH 2
294	N	CHF 2	0	O	COOCH 2 CH 3
295	N	CHF 2	0	O	NH 2
296	CH	CF 3	1	O	CH 3
297	CH	CF 3	1	O	COOCH 2 CH 3
298	CH	CF 3	1	O	CH 2 COOC(CH 3 ) 3
299	CH	CF 3	1	O	CHFCF 3
300	N	CF 3	0	O	CH 2 NHSO 2 CH 3
301	N	CF 3	0	O	(CH 2 ) 2 NHSO 2 CH 3
302	N	CF 3	0	O	CH 2 NHSO 2 CH 2 CH 3
303	N	CF 3	0	O	CH 2 NHSO 2 CH 2 C 6 H 5
304	CH	CF 3	0	O	(CH 2 ) 4 NHSO 2 CF 3
305	CH	CF 3	0	O	(CH 2 ) 2 S(CH 2 ) 2 CH 3
306	CH	CF 3	0	O	(CH 2 ) 4 S(CH 2 ) 4 OCH 3
307	CH	CF 3	0	S	(CH 2 ) 2 S(CH 2 ) 2 CN
308	CH	CF 3	0	S	CH 2 NHSO 2 CH 2 CH 3
309	CH	CF 3	0	S	CH 2 NHSO 2 CH 2 C 6 H 5
310	CH	CF 3	0	S	(CH 2 ) 2 NHSO 2 CH 3
311	CH	CF 3	0	S	CH 2 NHSO 2 CH 3
312	CH	CF 3	0	S	CH(CH 3 )CH 2 NHC 6 H 5
313	CH	CF 3	0	S	(CH 2 ) 2 S(2-F)—C 6 H 4
314	CH	CF 3	0	S	(CH 2 ) 6 NHCH 2 ) 6 OCH 3
315	CH	CF 3	0	S	(CH 2 ) 2 NH—(2-F)—C 6 H 4
316	CH	CF 3	0	S	(CH 2 ) 3 NHCH 2 CN
317	CH	CF 3	0	S	(CH 2 ) 2 O(3-Cl)—C 6 H 4
318	CH	CF 3	0	S	(CH 2 ) 6 NHCH 2 CF 3
319	CH	CF 3	0	S	(CH 2 ) 2 O(3-CH 3 )—C 6 H 4
320	CH	CF 3	0	O	CH 2 NHC 6 H 5
321	CH	CF 3	0	O	(CH 2 ) 4 S(2-Br)—C 6 H 4
322	CH	CF 3	0	O	(CH 2 ) 6 NH(CH 2 ) 2 OCH 3
323	CH	CF 3	0	O	(CH 2 ) 2 NH(CH 2 ) 4 OCH 3
324	CH	CF 3	0	O	(CH 2 ) 3 NH—(4-CN)—C 6 H 4
325	CH	CF 3	0	O	(CH 2 ) 2 O(3-CH 3 )—C 6 H 4
326	CH	CF 3	0	O	(CH 2 ) 4 NHCH 2 CF 3
327	CH	CF 3	0	O	(CH 2 ) 4 NHCH 2 CN
328	CH	CF 3	0	O	(CH 2 ) 3 O(4-OCH 3 )—C 6 H 4
329	CH	CF 3	0	O	CH 2 SO 2 -tert-C 4 H 9	oil
330	CH	CF 3	0	O	CH 2 SO 2 —(4-F)—C 6 H 4	oil
331	CH	CF 3	0	O	CH 2 SO 2 —C 6 H 5	oil
332	CH	CF 3	0	O	CH 2 SOCH 3	63
333	CH	CF 3	0	O	CH 2 SO—C 6 H 5	oil
334	CH	CF 3	0	O	CH 2 CONH(CH 2 ) 2 CH 3	80-82
335	CH	CF 3	0	O	(4-OCF 3 )—C 6 H 4	57-59
336	CH	CF 3	0	O	CH 2 OCH 3	oil
337	CH	CF 3	0	O		53-54
338	CH	CF 3	0	O		oil
339	CH	CF 3	0	O	CH 2 CH 2 OCH 2 CH 3	oil
340	CH	CF 3	0	O	CH 2 CH 2 NC 6 H 5	80-83
341	CH	CF 3	0	O		80-81
342	CH	CF 3	0	O		110-111
343	CH	CF 3	0	O	CH 2 CH 2 O(CO)—(4-Cl)—C 6 H 4	80-82
344	CH	CF 3	0	O	CH 2 —(4-OCH 3 )—C 6 H 4	54-55
345	CH	CF 3	0	O	CH 2 —(3-Cl)—C 6 H 4	51-52
346	CH	CF 3	0	O	CH 2 -cyclo-C 3 H 5	oil
347	CH	CF 3	0	O	CH 2 —(4-C 6 H 5 )—C 6 H 4	oil
348	CH	CF 3	0	O		143-144
349	CH	CF 3	0	O	CH 2 CH 2 O(CO)—(2,6-F 2 )—C 6 H 3	57-58
350	CH	CF 3	0	O	CH 2 CH 2 O(CO)—(4-NO 2 )—C 6 H 4	80-81
351	CH	CF 3	0	O	CH 2 —(2,6-Cl 2 )—C 6 H 3	91-92
352	CH	CF 3	0	O	CH 2 CH 2 OSO 2 CH 3	oil
353	CH	CF 3	0	O	CH 2 CH 2 O(CO)-tert-C 4 H 9	oil
354	CH	CF 3	0	O	CH 2 —(3-F)—C 6 H 4	50-51
355	CH	CF 3	0	O	CH 2 CONCH 2 C≡CH	129-131
356	CH	CF 3	0	O	CH 2 CH 2 O(CO)-cyclo-C 3 H 7	oil
357	CH	CF 3	0	O	CH 2 CH 2 O(CO)CH 3	oil
358	CH	CF 3	0	O	CH 2 —[2,4-(CH 3 ) 2 ]—C 6 H 3	85-86
359	CH	CF 3	0	O	CH 2 CONCH 2 CH═CH 2	210-212
360	CH	CF 3	0	O	CH 2 CON(CH 2 CH 3 ) 2	oil
361	CH	CF 3	0	O	CH 2 CON(CH 2 ) 3 CH 3	77-79
362	CH	CF 3	0	O	CH 2 CONCH 2 -(2-furyl)	139-141
363	CH	CF 3	0	O	CH 2 CONCH(CH 3 ) 2	112-114
364	CH	CF 3	0	O	CH 2 CONCH(CH 3 )[(CH 2 ) 4 CH 3 ]	73-75
365	CH	CF 3	0	O	CH 2 CONCH 2 CH 2 C 6 H 5	120-122
366	CH	CF 3	0	O	CH 2 CONCH 2 CH 2 OCH 2 CH 3	78
367	CH	CF 3	0	O	CH 2 CONCH 2 CF 3	176-178
368	CH	CF 3	0	O	CH 2 CONCH(CH 3 )[(CH 2 ) 5 CH 3 ]	85-86
369	CH	CF 3	0	O		oil
370	CH	CF 3	0	O		oil
371	CH	CF 3	0	O	CH 2 CH2-(1-pyrryl)	oil
372	CH	CF 3	0	O	CH 2 CH 2 C 6 H 5	oil
373	CH	CF 3	0	O	CH 2 Cl	53-54
374	CH	CF 3	0	O	(CH 2 ) 3 OH	38-39
375	CH	CF 3	0	O	CH 2 CONCH(CH 3 )[(CH 2 ) 2 ]CH 3	68-69
376	CH	CF 3	0	O	CH 2 CH(OCH 3 ) 2	oil
377	CH	CF 3	0	O	CH 2 CONCH 2 C(CH 3 ) 3	oil
378	CH	CF 3	0	O	CH 2 CONC(CH 3 ) 2 (CH 2 CH 3 )	oil
379	CH	CF 3	0	O	CH 2 CONCH 2 CH 2 -cyclo-C 6 H 11	82-85
380	CH	CF 3	0	O	CH 2 CONCH(CH 3 )(1-naphthyl)	142-146
381	CH	CF 3	0	O	(CH 2 ) 3 Cl	oil
382	CH	CF 3	0	O	CH 2 CON-tert-C 4 H 9	oil
383	CH	CF 3	0	O	CH 2 CON(iso-C 3 H 7 ) 2	70-72
384	CH	CF 3	0	O	CH 2 CON(CH 2 ) 7 CH 3	79-81
385	CH	CF 3	0	O	CH 2 CON-cyclo-C 6 H 11	119-121
386	CH	CF 3	0	O	CH 2 CONCH 2 CH 2 —(4-Cl)—C 6 H 4	120-121
387	CH	CF 3	0	O	CH 2 CONCH 2 -(2-thienyl)	137-139
388	CH	CF 3	0	O		151-153
389	CH	CF 3	0	O	CH 2 CONHCH(CH 3 )(CH 2 CH 3 )	87-89
390	CH	CF 3	0	O	(CH 2 ) 3 SCH 3	oil
391	CH	CF 3	0	O	(CH 2 ) 3 SOCH 3	oil
392	CH	CF 3	0	O	CH 2 CONC(CH 3 ) 2 (C≡CH)	111-113
393	CH	CF 3	0	O	CH 2 CONCH(CH 3 )CH 2 CH 2 CH(CH 3 ) 2	72-74
394	CH	CF 3	0	O		oil
395	CH	CF 3	0	O	CH 2 CON-cyclo-C 5 H 9	110-112
396	CH	CF 3	0	O	CH 2 CON(CH 2 ) 4 CH 3	75-77
397	CH	CF 3	0	O		190-192
398	CH	CF 3	0	O	CH 2 CON(3-CF 3 )C 6 H 4	136-138
399	CH	CF 3	0	O	CH 2 CON-cyclo-C 8 H 17	115-117
400	CH	CF 3	0	O		oil
401	CH	CF 3	0	O	CH 2 CON-Adamantyl	oil
402	CH	CF 3	0	O	CH 2 CON(CH 2 CH 2 CH 3 ) 2	oil
403	CH	CF 3	0	O	CH 2 CONCH(CH 3 )[(4-F)—C 6 H 4 ]	111-113
404	CH	CF 3	0	O	CH 2 CONCH 2 CH(CH 3 ) 2	91-93
405	CH	CF 3	0	O		Oil
406	CH	CF 3	0	O	CH 2 CONCH 2 CH 2 OC 6 H 5	99-101
407	CH	CF 3	0	O	CH 2 CH═NOCH 3	oil
408	CH	CF 3	0	O	CH 2 CONCH 2 CH 2 —[3,4-(OCH 3 ) 2 ]C 6 H 3	123-125
409	CH	CF 3	0	O	CH 2 CON—(2-Cl)C 6 H 4	138-140
410	CH	CF 3	0	O	CH 2 CON—(2-SCH 3 )C 6 H 4	136-138
411	CH	CF 3	0	O		222-225
412	CH	CF 3	0	O		207-209
413	CH	CF 3	0	O	CH 2 CON—(3-Br)C 6 H 4	129-131
414	CH	CF 3	0	O	CH 2 CON—N—(2,4,6-Cl 3 )C 6 H 2	153-155
415	CH	CF 3	0	O	CH 2 CON—(4-I)C 6 H 4	143-145
416	CH	CF 3	0	O	CH 2 CON—NCOCH 2 (3-Thienyl)	185-187
417	CH	CF 3	0	O	CH 2 CH 2 CHO	oil
418	CH	CF 3	0	O	CH 2 CON(CH 3 )[(CH 2 ) 3 CH 3 ]	oil
419	CH	CF 3	0	O	CH 2 CON—(3,5-Cl 2 -2,4-F 2 )C 6 H	166-167
420	CH	CF 3	0	O	CH 2 CON—C 6 H 5	215-217
421	CH	CF 3	0	O	CH 2 CON(CH 3 )(C 6 H 11 )	oil
422	CH	CF 3	0	O	CH 2 CON(CH 2 CH 3 )(CH 2 CH═CH 2 )	oil
423	CH	CF 3	0	O	CH 2 CON(CH 2 CH 3 )[CH(CH 3 ) 2 ]	oil
424	CH	CF 3	0	O	CH 2 CONCH(CH 3 )[(CH 3 ) 2 ]	108-110
425	CH	CF 3	0	O	CH 2 CON(CH 2 CH 3 )[CH 2 C(═CH 2 )(CH 3 )]	oil
426	CH	CF 3	0	O	CH 2 CONCH 2 (4-tert-C 4 H 9 )C 6 H 4	oil
427	CH	CF 3	0	O	CH 2 CONCH(CH 3 )(tert-C 4 H 9 )	oil
428	CH	CF 3	0	O	CH 2 CONCH(CH 3 )[CH 2 CH(CH 3 )(CH 2 CH 3 )]	oil
429	CH	CF 3	0	O	CH 2 CONCH 2 COOCH 2 CH 3	103-105
430	CH	CF 3	0	O	CH 2 CON[(CH 2 ) 2 CH 3 ](CH 2 -cyclo-C 3 H 7 )	oil
431	CH	CF 3	0	O	CH 2 CONCH(CH 3 )CH 2 CH 2 CH(CH 3 ) 2	80-82
432	CH	CF 3	0	O	CH 2 CONCH(CH 2 CH 3 )[CH 2 CH(CH 3 ) 2 ]	oil
433	CH	CF 3	0	O	CH 2 C═O-(1-Piperidinyl)	oil
434	CH	CF 3	0	O		180-182
435	CH	CF 3	0	O	CH 2 CONCH 2 C(═CH2)(CH 3 )	86-87
436	CH	CF 3	0	O	CH 2 CONCH[CH(CH 3 ) 2 ](COOCH 3 )	oil
437	CH	CF 3	0	O	CH 2 CONCH 2 -cyclo-C 3 H 7	oil
438	CH	CF 3	0	O	CH 2 CON(CH 2 ) 5 OH	oil
439	CH	CF 3	0	O	CH 2 CON(CH 3 )(CH 2 CO 2 CH 3 )	oil
440	CH	CF 3	0	O	CH 2 CON(CH 3 )(CH 2 CN)	oil
441	CH	CF 3	0	O	CH 2 CONCH[CH 2 CH(CH 3 ) 2 ](CO 2 CH 3 )	oil
442	CH	CF 3	0	O	CH 2 CON-(1-Piperidinyl)	oil
443	CH	CF 3	0	O	CH 2 CONCH 2 CH 2 OCH 3	97-99
444	CH	CF 3	0	O	CH 2 CH 2 SC 6 H 5	oil
445	CH	CF 3	0	O	CH 2 CH 2 SCH 3	oil
446	CH	CF 3	0	O	CH 2 CH 2 SCH 2 C 6 H 5	oil
447	CH	CF 3	0	O		oil
448	CH	CF 3	0	O	CH 2 CON—(2-OH)C 6 H 4	162-164
449	CH	CF 3	0	O	CH 2 CON—(3-OH)C 6 H 4	oil
450	CH	CF 3	0	O	CH 2 CON—(2-CH 3 )C 6 H 4	163-164
451	CH	CF 3	0	O	CH 2 CON—(3-NO 2 )C 6 H 4	176-178
452	CH	CF 3	0	O	CH 2 CON—(3-OCF 2 CHFCl)C 6 H 4	120-121
453	CH	CF 3	0	O	CH 2 CON—(3-CF 3 -4-F)C 6 H 3	168-170
454	CH	CF 3	0	O	CH 2 CON—(2,4-Cl 2 )C 6 H 3	120-122
455	CH	CF 3	0	O	CH 2 CON—(2-F-4.Cl)C 6 H 3	148-151
456	CH	CF 3	0	O	CH 2 CON—[2,4-(CH 3 ) 2 ]C 6 H 3	123-125
457	CH	CF 3	0	O	CH 2 CON—[2,3-(CH 3 ) 2 ]C 6 H 3	waxy
458	CH	CF 3	0	O		waxy
459	CH	CF 3	0	O	CH 2 CON—(2-CH 3 -3-Cl)C 6 H 3	160-162
460	CH	CF 3	0	O	CH 2 CON(CH 2 CH 3 )(C 6 H 5 )	oil
461	CH	CF 3	0	O		124-126
462	CH	CF 3	0	O	CH 2 CON(2-OCH 3 -5-Ph)C 6 H 3	167-169
463	CH	CF 3	0	O		157-158
464	CH	CF 3	0	O	CH 2 CON—(3-NO 2 -4-Cl)C 6 H 3	oil
465	CH	CF 3	0	O	CH 2 CON—(2-Cl-4-CH 3 )C 6 H 3	106-108
466	CH	CF 3	0	O	CH 2 CON—(3-OCH 2 CH 3 )C 6 H 4	waxy
467	CH	CF 3	0	O		169-171
468	CH	CF 3	0	O	CH 2 CON—(4-CH 3 )C 6 H 4	139-141
469	CH	CF 3	0	O	CH 2 CON-(1-Naphthyl)	155-157
470	CH	CF 3	0	O	CH 2 CON—(3-I)C 6 H 4	135-137
471	CH	CF 3	0	O	CH 2 CON—(2-OCH 2 CH 3 )C 6 H 4	138
472	CH	CF 3	0	O	CH 2 CON—(2-OCH 3 )C 6 H 4	130-132
473	CH	CF 3	0	O	CH 2 CON—[3,5-(OCH 3 ) 2 ]C 6 H 3	130-132
474	CH	CF 3	0	O	CH 2 CON—(4-Cl)C 6 H 4	139-141
475	CH	CF 3	0	O	CH 2 CON—(3-CH 3 )C 6 H 4	oil
476	CH	CF 3	0	O	CH 2 CON—(3-OCH 3 )C 6 H 4	oil
477	CH	CF 3	0	O	CH 2 CON—(4-CH 2 CH 3 )C 6 H 4	122-123
478	CH	CF 3	0	O	CH 2 CON—(4-CF 3 )C 6 H 4	151-152
479	CH	CF 3	0	O	CH 2 CON—(2-CH 3 -4-Cl)C 6 H 3	165-167
480	CH	CF 3	0	O	CH 2 CH 2 NCH 2 C 6 H 5	oil
481	CH	CF 3	0	O	CH 2 CH 2 NCH 2 -(3-Pyridyl)	oil
482	CH	CF 3	0	O	CH 2 CH═NOCH 2 CH 3	oil
483	CH	CF 3	0	O	CH 2 CH═NOC 6 H 5	oil
484	CH	CF 3	0	O	CH 2 CON—(4-NO 2 )C 6 H 4	181-183
485	CH	CF 3	0	O	CH 2 CON—(2-CH 3 -4-NO 2 )C 6 H 3	129-131
486	CH	CF 3	0	O	CH 2 CON—(2-Cl-3-CF 3 )C 6 H 3	136
487	CH	CF 3	0	O	CH 2 CON—(2-CN-4-Cl)C 6 H 3	157-159
488	CH	CF 3	0	O	CH 2 CON—(3,5-Cl 2 )C 6 H 3	167-169
489	CH	CF 3	0	O	CH 2 CON—(3,5-Cl 2 -4-OCF 2 CHF 2 )C 6 H 2	132-134
490	CH	CF 3	0	O	CH 2 CON—(2,4,5-Cl 3 )C 6 H 2	146
491	CH	CF 3	0	O	CH 2 CON—(3,5-Cl 2 -4-OCF 2 CHFCF 3 )C 6 H 2	124-126
492	CH	CF 3	0	O	CH 2 CON—(2-CF 3 -4-Cl)C 6 H 3	136
493	CH	CF 3	0	O		oil
494	CH	CF 3	0	O		91-93
495	CH	CF 3	0	O		123-125
496	CH	CF 3	0	O		81-83
497	CH	CF 3	0	O		113-115
498	CH	CF 3	0	O	COOH	155-157
499	CH	CF 3	0	O	4-F—C 6 H 4	104-106
500	CH	CF 3	0	O	CON(C 2 H 5 ) 2	oil
501	CH	CF 3	0	O	CONCH(CH 3 ) 2	oil
502	CH	CF 3	0	O	CON(CH 3 ) 2	52-54
503	CH	CF 3	0	O	CONHCH 2 CCH	105-107
504	CH	CF 3	0	O	CONH-cyclo-C 3 H 5	101-103
505	CH	CF 3	0	O	CONH 2	206-208
506	CH	CF 3	0	O		72-74
507	CH	CF 3	0	O		98-100
508	CH	CF 3	0	O		108-110
509	CH	CF 3	0	O		140-142
510	CH	CF 3	0	O	CONHCH 3	127-129
511	CH	CF 3	0	O	CONHCH 2 CH═CH 2	oil
512	CH	CF 3	0	O	CON(CH 2 CN) 2	90-92
513	CH	CF 3	0	O	4-(t-C 4 H 9 )—C 6 H 4	64-66
514	CH	CF 3	0	O	4-CF 3 -C 6 H 4	89-91
515	CH	CF 3	0	O	4-CH 3 -3-F—C 6 H 3	104-106
516	CH	CF 3	0	O	2,4-di-Cl—C 6 H 3	70-72
517	CH	CF 3	0	O	4-(NHSO 2 CH 3 )—C 6 H 4	204-206
518	CH	CF 3	0	O	2,6-di-Cl—C 6 H 3	139-141
519	CH	CF 3	0	O	COOCH 2 C 6 H 5	83-85
520	CH	CF 3	0	O	CONHC 3 H 7	oil
521	CH	CF 3	0	O	3,5-di-Br-4-(OCH 3 )—C 6 H 2	132-134
522	CH	CF 3	0	O	CHCl 2	oil
523	CH	CF 3	0	O	CCl 3	oil
524	CH	CF 3	0	O	CH(OCH3) 2	oil
525	CH	CF 3	0	O	3-CF 3 —C 6 H 4	57-59
526	CH	CF 3	0	O	CON(CH 2 ) 5	oil
527	CH	CF 3	0	O	CON(CH 3 )CH 2 C 6 H 5	oil
528	CH	CF 3	0	O	CONHCH 2 C 6 H 5	96-98
529	CH	CF 3	0	O		oil
530	CH	CF 3	0	O	CONH-n-C 6 H 13	oil
531	CH	CF 3	0	O	CON(CH 2 CH 3 )CH 2 C 6 H 5	oil
532	CH	CF 3	0	O	CONH-c-C 6 H 11	115-117
533	CH	CF 3	0	O	CON(n-C 4 H 9 ) 2	oil
534	CH	CF 3	0	O		oil
535	CH	CF 3	0	O	CONH-i-C 4 H 9	oil
536	CH	CF 3	0	O		oil
537	CH	CF 3	0	O	CON(CH 2 ) 4	68-70
538	CH	CF 3	0	O	CON(CH 3 )-n-C 6 H 13	oil
539	CH	CF 3	0	O		oil
540	CH	CF 3	0	O	CON(CH 3 )CH 2 CH 3	oil
541	CH	CF 3	0	O	CONHOCH 3	oil
542	CH	CF 3	0	O		oil
543	CH	CF 3	0	O	CON(CH 3 )CH 2 CH 2 CH 3	oil
544	CH	CF 3	0	O	CONHCH 2 CH(OCH 3 ) 2	oil
545	CH	CF 3	0	O	CONH-t-C 4 H 9	113-115
546	CH	CF 3	0	O	CONHCH 2 -4-Cl—C 6 H 4	oil
547	CH	CF 3	0	O	CONHCH(CH 3 )C 6 H 5	oil
548	CH	CF 3	0	O	CONHCH 2 CH 2 OCH 3	92-94
549	CH	CF 3	0	O		190-192
550	CH	CF 3	0	O	CONHC(CH 3 ) 2 CCH	90-92
551	CH	CF 3	0	O	CONHCH 2 -2-Furyl	93-95
552	CH	CF 3	0	O	CON(CH 2 ) 3	91-93
553	CH	CF 3	0	O	CONHCH 2 -c-C 3 H 5	oil
554	CH	CF 3	0	O	CONHC(CH 3 ) 2 CH 2 CH 3	oil
555	CH	CF 3	0	O	CONH(CH 2 ) 3 C 6 H 5	oil
556	CH	CF 3	0	O	CONHCH 2 -3-Pyridyl	132-134
557	CH	CF 3	0	O	CON(CH 3 )-n-C 4 H 9	oil
558	CH	CF 3	0	O	CON(CH 2 CH3)-i-C 3 H 7	oil
559	CH	CF 3	0	O		oil
560	CH	CF 3	0	O	CONHCH 2 CH 2 Cl	oil
561	CH	CF 3	0	O	CONHCH 2 CN	152-157
562	CH	CF 3	0	O	CON(CH 3 )OCH 3	oil
563	CH	CF 3	0	O	CON(CH 3 )CH 2 CH═CH 2	oil
564	CH	CF 3	0	O	CONHCH 2 COOCH 3	oil
565	CH	CF 3	0	O	CON(CH 3 )-i-C 3 H 7	oil
566	CH	CF 3	0	O	CON(CH 3 )CH 2 CH 2 CN	oil
567	CH	CF 3	0	O	CON(CH 3 )CH 2 CH(OCH 3 ) 2	oil
568	CH	CF 3	0	O	CON(CH 3 )CH 2 CH(—CH 2 CH 2 O—)	oil
569	CH	CF 3	0	O	CONHCH 2 C(═CH 2 )CHH 3	oil
570	CH	CF 3	0	O	CON(CH 2 CH 3 )CH 2 CH═CH 2	oil
571	CH	CF 3	0	O	CONHC 6 H 5	83-85
572	CH	CF 3	0	O	CON(CH 3 )CH 2 CCH	oil
573	CH	CF 3	0	O	CON(CH 3 )CH 2 CN	oil
574	CH	CF 3	0	O	CON(CH 3 )CH 2 CH 2 N(CH 3 ) 2	oil
575	CH	CF 3	0	O	CONHOCH 2 CH 3	114-116
576	CH	CF 3	0	O	CONHCH 2 CF 3	74-76
577	CH	CF 3	0	O	CON(CH 2 CH 2 Cl) 2	oil
578	CH	CF 3	0	O	CONH-c-C 4 H 7	oil
579	CH	CF 3	0	O	CON(CH 2 CH 2 CH 3 )CH 2 -c-C 3 H 5	oil
580	CH	CF 3	0	O	CON(CH 3 )-c-C 6 H 11	oil
581	CH	CF 3	0	O	CON(CH 2 CH 3 )CH 2 C(═CH 2 )CH 3	oil
582	CH	CF 3	0	O	CONHOCH 2 CH═CH 2	90-92
583	CH	CF 3	0	O	CONHOCH 2 C 6 H 5	126-128
584	CH	CF 3	0	O	CON(CH 3 )CH 2 COOCH 3	oil
585	CH	CF 3	0	O	COONHCH 3	230-232
586	CH	CF 3	0	O	CONHCH 2 CH 3	83-85
587	CH	CF 3	0	O	CONHCH(CH 3 )COOCH 3	104-106
588	CH	CF 3	0	O	CONHCH(i-C 3 H 7 )COOCH 3	oil
589	CH	CF 3	0	O	CON(CH 3 )CH 2 CON(CH 3 ) 2	oil
590	CH	CF 3	0	O	CON(CH 3 )-t-C 4 H 9	oil
591	CH	CF 3	0	O	CONHO-t-C 4 H 9	103-105
592	CH	CF 3	0	O	CON(CH 3 )CH(i-C 3 H 7 )COOCH 3	oil
593	CH	CF 3	0	O	CH(OCH 2 CH 3 ) 2	oil
594	CH	CF 3	0	O		oil
595	CH	CF 3	0	O		oil
596	CH	CF 3	0	O		oil
597	CH	CF 3	0	O		oil
598	CH	CF 3	0	O		oil
599	CH	CF 3	0	O	CONHCH 2 CONHCH 3	101-103
600	CH	CF 3	0	O	CON(CH 2 ) 7	oil
601	CH	CF 3	0	O	CON(CH 2 ) 6	oil
602	CH	CF 3	0	O	CON(CH 2 CH 3 )CH 2 CH 2 OCH 3	oil
603	CH	CF 3	0	O		oil
604	CH	CF 3	0	O		oil
605	CH	CF 3	0	O		oil
606	CH	CF 3	0	O	CON(CH 2 CH 3 )CH 2 CH 2 CN	oil
607	CH	CF 3	0	O		oil
608	CH	CF 3	0	O	CON(CH 2 CH 3 )-n-C 4 H 9	oil
609	CH	CF 3	0	O		179-181
610	CH	CF 3	0	O	CONHCH(CH 3 )CONHCH 3	136-138
611	CH	CF 3	0	O	COON(CH 2 ) 4	64-66
612	CH	CF 3	0	O	CONHCH 2 CON(CH 3 ) 2	107-109
613	CH	CF 3	0	O	CON(CH 2 COOCH 2 CH 3 ) 2	oil
614	CH	CF 3	0	O		180-182
615	CH	CF 3	0	O		221-223
616	CH	CF 3	0	O		234-236
617	CH	CF 3	0	O		oil
618	CH	CF 3	0	O	CON(CH 3 )CH 2 -6-Cl-3-pyridyl	oil
619	CH	CF 3	0	O		105-107
620	CH	CF 3	0	O	CONHCH(CH 3 )CH(OCH 3 ) 2	oil
621	CH	CF 3	0	O	CONHCH 2 CH 2 SCH 3	oil
622	CH	CF 3	0	O	CONHCH(CH 3 )CH 2 OCH 3	70-72
623	CH	CF 3	0	O	CONHCH 2 CH 2 NHCOCH 3	124-126
624	CH	CF 3	0	O	CONH(CH 2 ) 3 OCH 2 CH 3	oil
625	CH	CF 3	0	O	CON(CH 2 CH 3 )CH 2 CH 2 CH 3	oil
626	CH	CF 3	0	O	CON(CH 2 CH 3 )CH 2 OCH 3	oil
627	CH	CF 3	0	O	CONHCH 2 CH 2 SCH 2 CH 3	oil
628	CH	CF 3	0	O	CONHCH 2 CH 2 OCH 2 CH 3	59-61
629	CH	CF 3	0	O		oil
630	CH	CF 3	0	O		174-176
631	CH	CF 3	0	O	CONHCH(CH 3 )CH(OCH 3 ) 2	oil
632	CH	CF 3	0	O	CONHCH 2 CH 2 SCH 3	oil
633	CH	CF 3	0	O	CONHCH(CH 3 )CH 2 OCH 3	70-72
634	CH	CF 3	0	O	CONHCH 2 CH 2 NHCOCH 3	124-126
635	CH	CF 3	0	O	CONH(CH 2 ) 3 OCH 2 CH 3	oil
636	CH	CF 3	0	O	CON(CH 2 CH 3 )CH2CH 2 CH 3	oil
637	CH	CF 3	0	O	CON(CH 2 CH 3 )CH 2 OCH 3	oil
638	CH	CF 3	0	O	CONHCH 2 CH 2 SCH 2 CH 3	oil
639	CH	CF 3	0	O	CONHCH(CH 3 )CH 2 COOCH 2 CH 3	oil
640	CH	CF 3	0	O	CONH-4-COOCH 3 —C 6 H 4	189-191
641	CH	CF 3	0	O	CONH-4-CONH 2 —C 6 H 4	265-267
642	CH	CF 3	0	O	CONHCH 2 CH 2 Br	oil
643	CH	CF 3	0	O	CONHCH 2 CH═CHCH 2 Cl	oil
644	CH	CF 3	0	O	CONH-4-CONHCH 3 —C 6 H 4	219-221
645	CH	CF 3	0	O	CONHCH 2 CH 2 CH 2 Br	oil
646	CH	CF 3	0	O	CONHCH 2 CH 2 CH 2 OCH 3	oil
647	CH	CF 3	0	O	CONH-4-CH 2 CH 3 —C 6 H 4	97-99
648	CH	CF 3	0	O	CONHCH 2 CH 2 OCH(CH 3 ) 2	oil
649	CH	CF 3	0	O	CONHCH 2 CH 2 CH 2 OCH 2 CH 3	oil
650	CH	CF 3	0	O		oil
651	CH	CF 3	0	O		64-66
652	CH	CF 3	0	O		oil
653	CH	CF 3	0	O		oil
654	CH	CF 3	0	O	CH 2 CON(CH 3 )CH 2 CH 3	oil
655	CH	CF 3	0	O	CH 2 CON(CH 3 ) 2	58-60
656	CH	CF 3	0	O	CH 2 CON(CH 2 ) 4	101-103
657	CH	CF 3	0	O		oil
658	CH	CF 3	0	O		90-92
659	CH	CF 3	0	O	CH 2 CONHCH 2 CH 3	104-106
660	CH	CF 3	0	O	CH 2 CON(CH 3 )CH 2 CH 2 OH	oil
661	CH	CF 3	0	O	CH 2 CON(CH 3 )CH 2 CH 2 CH 3	oil
662	CH	CF 3	0	O	CH 2 CON(CH 3 )CH 2 CH(—OCH 2 CH 2 O—)	oil
663	CH	CF 3	0	O	CH 2 CONHCH 2 CH 3	104-106
664	CH	CF 3	0	O	CH 2 CON(CH 3 )CH 2 CH 2 OH	oil
665	CH	CF 3	0	O	CH 2 CON(CH 3 )CH 2 CH 2 CH 3	oil
667	CH	CF 3	0	O	CH 2 CON(CH 3 )CH 2 CH(—OCH 2 CH 2 O—)	oil
668	CH	CF 3	0	O		79-81
669	CH	CF 3	0	O	CH 2 CONHCH 2 CH 2 SCH 3	65-67
670	CH	CF 3	0	O	CH 2 CONHCH(CH 3 )CH 2 OCH 3	86-88
671	CH	CF 3	0	O	CON(CH 3 )CH 2 CH2OCO-c-C 4 H 7	oil
672	CH	CF 3	0	O	CH 2 CONHCH 2 CH 2 Br	87-89
673	CH	CF 3	0	O	CON(CH 3 )CH 2 CH 2 OCOC 6 H 5	oil
674	CH	CF 3	0	O	CON(CH 3 )CH 2 CH 2 OCO-c-C 3 H 5	oil
675	CH	CF 3	0	O	CONH-2-CH 3 —C 6 H 4	104-106
676	CH	CF 3	0	O	CH 2 CON(i-C 3 H 7 )-4-F—C 6 H 4	102-104
677	CH	CF 3	0	O		oil
678	CH	CF 3	0	O		oil
679	CH	CF 3	0	O	CON(CH 3 )CH 2 CH 2 OCONHC 6 H 5	100-102
680	CH	CF 3	0	O	CON(CH 3 )CH 2 CH 2 OCONHCH 2 CH 3	oil
681	CH	CF 3	0	O	CON(CH 3 )CH 2 CH 2 OSO 2 CH 3	oil
682	CH	CF 3	0	O	CH 2 CONH-c-C 4 H 7	133-135
683	CH	CF 3	0	O	CH 2 CONHCH 2 CN	158-160

TABLE 2
					m.p.
No.	X	Y	W	R 1	[° C.]
684	N	(CF 2 ) 3 CHF 2	O	CH 3
685	N	(CF 2 ) 2 CF 3	O	CH 2 CH 3
686	N	(CF 2 ) 2 CF 3	O	COOCH 2 CH 3
687	N	(CF 2 ) 2 CF 3	O	OH
688	N	(CF 2 ) 2 CF 3	O	OCH 3
689	N	CF 2 CF 3	O	CH 3
690	N	CF 2 CF 3	O	CH 2 CH 3
691	N	CF 2 CF 3	S	CH 3
692	N	CF 2 CF 3	S	CH 2 CH 3
693	N	CF 2 CF 3	S	(CH 2 ) 2 CH 3
694	CH	CF 3	O	CH 3	oil
695	CH	CF 3	O	CH 2 CH 3
696	CH	CF 3	O	(CH 2 ) 2 CH 3
697	CH	CF 3	O	CH(CH 3 ) 2
698	CH	CF 3	O	(CH 2 ) 3 CH 3
699	CH	CF 3	O	CH(CH 3 )CH 2 CH 3
700	CH	CF 3	O	CH 2 CH(CH 3 ) 2
701	CH	CF 3	O	C(CH 3 ) 3	oil
702	CH	CF 3	O	(CH 2 ) 4 CH 3
703	CH	CF 3	O	CH(CH 3 )(CH 2 ) 2 CH 3
704	CH	CF 3	O	(CH 2 ) 2 CH(CH 3 ) 2
705	CH	CF 3	O	CH 2 C(CH 3 ) 3
706	CH	CF 3	O	Cyclo-C 5 H 9
707	CH	CF 3	O	Cyclo-C 6 H 11
708	CH	CF 3	O	CHO
709	CH	CF 3	O	CH═CH 2
710	CH	CF 3	O	CH 2 CH═C(CH 3 ) 2
711	CH	CF 3	O	CH 2 CH═CH 2
712	CH	CF 3	O	C(CH 3 )═CH 2
713	CH	CF 3	O	(CH 2 ) 5 C═CH 2
714	CH	CF 3	O	C(═CHCH 3 )CH 3
715	CH	CF 3	O	CH 2 C≡CH
716	CH	CF 3	O	CH 2 CH 2 C≡CH
717	CH	CF 3	O	CH 2 C≡CCH 2 CH 3
718	CH	CF 3	O	(CH 2 ) 4 C≡CH
719	CH	CF 3	O	CHFCF 3
720	CH	CF 3	O	COOCH 2 CH 3
721	CH	CF 3	O	CH 2 CH 2 OH
722	CH	CF 3	O	CH 2 CH 2 OCH 3
723	CH	CF 3	O	CH 2 COOC(CH 3 ) 3
724	CH	CF 3	O	CH 2 SC 6 H 5
725	CH	CF 3	O	CH 2 CONHCH 3
726	CH	CF 3	O	CH 2 CH(OH)CH 2 OH
727	CH	CF 3	O	CH 2 COCH 3
728	CH	CF 3	O	COCH3
729	CH	CF 3	O	CH 2 OC 6 H 5
730	CH	CF 3	O	COC 6 H 5
731	CH	CF 3	O	CF 2 CH 3
732	CH	CF 3	O	CH 2 CN
733	CH	CF 3	O	CH 2 CH(—O—)CH 2
734	CH	CF 3	O	CH 2 (4-OCH 3 )C 6 H 5
735	CH	CF 3	O	CH 2 CH(OH)CH 2 SC 6 H 5
736	CH	CF 3	O	CH═CF 2
737	CH	CF 3	O	CCl═CHCl
738	CH	CF 3	O	2-Pyridyl
739	CH	CF 3	O	OC 6 H 5
740	CH	CF 3	O	OH
741	CH	CF 3	O	OCH 3
742	CH	CF 3	O	OCH 2 CH 3
743	CH	CF 3	O	OCHF 2
744	CH	CF 3	O	OCH 2 C 6 H 5
745	CH	CF 3	O	SCH 3
746	CH	CF 3	O	SC 6 H 5
747	CH	CF 3	O	NH 2
748	CH	CF 3	O	NHCH 3
749	CH	CF 3	O	NHCH 2 CH 3
750	CH	CF 3	O	N(CH 2 CH 3 ) 2
751	CH	CF 3	O	N(CH 2 CN) 2
752	CH	CF 3	O	N(CH 3 ) 2
753	CH	CF 3	O	NHCOCH 3
754	CH	CF 3	O	NHCOCH 2 CH 3
755	CH	CF 3	O	OSO 2 CH 3
756	CH	CF 3	O	SOCH 2 (4-Br)—C 6 H 4
757	CH	CF 3	O	N(CH 3 )COOCH 2 C 6 H 5
758	N	CF 3	O	CH 3
759	N	CF 3	O	CH 2 CH 3
760	N	CF 3	O	(CH 2 ) 2 CH 3
761	N	CF 3	O	CH(CH 3 ) 2
762	N	CF 3	O	(CH 2 ) 3 CH 3
763	N	CF 3	O	CH 2 CH(CH 3 ) 2
764	N	CF 3	O	C(CH 3 ) 3
765	N	CF 3	O	CH 2 C(CH 3 ) 3
766	N	CF 3	O	Cyclo-C 5 H 9
767	N	CF 3	O	Cyclo-C 6 H 11
768	N	CF 3	O	CH 2 C═C(CH 3 ) 2
769	N	CF 3	O	CH 2 CH 2 C═CH 2
770	N	CF 3	O	CH 2 CH═CH 2
771	N	CF 3	O	(CH 2 ) 5 CH═CH 2
772	N	CF 3	O	CH 2 C≡CH
773	N	CF 3	O	CH 2 C≡CCH 2 CH 3
774	N	CF 3	O	CHFCF 3
775	N	CF 3	O	COOCH 2 CH 3
776	N	CF 3	O	CH 2 CH 2 OH
777	N	CF 3	O	CH 2 CH 2 OCH 3
778	N	CF 3	O	CH 2 COOC(CH 3 ) 3
779	N	CF 3	O	CH 2 SC 6 H 5
780	N	CF 3	O	CH 2 CONHCH 3
781	N	CF 3	O	CH 2 CH(OH)CH 2 OH
782	N	CF 3	O	CHO
783	N	CF 3	O	COCH 3
784	N	CF 3	O	CH 2 OC 6 H 5
785	N	CF 3	O	COC 6 H 5
786	N	CF 3	O	CF 2 CH 3
787	N	CF 3	O	CH 2 CN
788	N	CF 3	O	CH 2 CH 2 CN
789	N	CF 3	O	CH═CF 2
790	N	CF 3	O	2-Furyl
791	N	CF 3	O	OH
792	N	CF 3	O	OCH 3
793	N	CF 3	O	OCH 2 CH 3
794	N	CF 3	O	OCHF 2
795	N	CF 3	O	OCH 2 C 6 H 5
796	N	CF 3	O	NH 2
797	N	CF 3	O	NHCH 3
798	N	CF 3	O	NHCH 2 CH 3
799	N	CF 3	O	N(CH 2 CH 3 ) 2
800	N	CF 3	O	N(CH 2 CN) 2
801	N	CF 3	O	N(CH 3 ) 2
802	N	CF 3	O	NHCOCH 3
803	N	CF 3	O	NHCOCH 2 CH 3
804	N	CF 3	O	OSO 2 CH 3
805	CH	CF 3	S	CH 3
806	CH	CF 3	S	CH 2 CH 3
807	CH	CF 3	S	(CH 2 ) 2 CH 3
808	CH	CF 3	S	CHO
809	CH	CF 3	S	CHFCF 3
810	CH	CF 3	S	CH 2 C≡CH
811	CH	CF 3	S	COOCH 2 CH 3
812	CH	CF 3	S	CH 2 COOC(CH 3 ) 3
813	CH	CF 3	S	CH 2 CN
814	N	CF 3	S	CH 3
815	N	CF 3	S	CH 2 CH 3
816	N	CF 3	S	(CH 2 ) 2 CH 3
817	N	CF 3	S	CHFCF 3
818	N	CF 3	S	CH 2 CH 2 OH
819	N	CF 3	S	CH 2 COOC(CH 3 ) 3
820	N	CH 2 CH 2 Cl	O	CH 2 CH 3
821	N	CH 2 CH 2 Cl	O	NH 2
822	N	CH 2 Cl	O	CH 3
823	CH	CHF 2	O	CH 3
824	CH	CHF 2	O	CH 2 CH 3
825	CH	CHF 2	O	(CH 2 ) 2 CH 3
826	CH	CHF 2	O	CH 2 C═CH 2
827	CH	CHF 2	O	C(CH 3 )═CH 2
828	CH	CHF 2	O	COOCH 2 CH 3
829	CH	CHF 2	O	CH 2 CONHCH 3
830	CH	CHF 2	O	CF 2 CH 3
831	CH	CHF 2	O	CHO
832	CH	CHF 2	O	NH 2
833	CH	CHF 2	O	NHCOCH 3
834	N	CHF 2	O	CH 3
835	N	CHF 2	O	CH 2 CH 3
836	N	CHF 2	O	CH(CH 3 )(CH 2 ) 4 CH 3
837	N	CHF 2	O	CH 2 CH═CH 2
838	N	CHF 2	O	COOCH 2 CH 3
839	N	CHF 2	O	NH 2

TABLE 3
						m.p.
No.	X	Y	m	V	R 1	[° C.]
840	N	(CF 2 ) 3 CHF 2	0	O	CH 3
841	N	(CF 2 ) 2 CF 3	0	O	CH 2 CH 3
842	N	(CF 2 ) 2 CF 3	0	O	COOCH 2 CH 3
843	N	(CF 2 ) 2 CF 3	0	O	SH
844	N	(CF 2 ) 2 CF 3	0	O	SCH 3
845	N	(CF 2 ) 2 CF 3	0	O	SCH 2 C≡CH
846	N	CF 2 CF 3	0	O	CH 3
847	N	CF 2 CF 3	0	O	CH 2 CH 3
848	N	CF 3	0	O	CH 3
849	N	CF 3	0	O	CH 2 CH 3
850	N	CF 3	0	O	(CH 2 ) 2 CH 3
851	N	CF 3	0	O	CH(CH 3 ) 2
852	N	CF 3	0	O	(CH 2 ) 3 CH 3
853	N	CF 3	0	O	CH 2 CH(CH 3 ) 2
854	N	CF 3	0	O	C(CH 3 ) 3
855	N	CF 3	0	O	CH 2 C(CH 3 ) 3
856	N	CF 3	0	O	Cyclo-C 5 H 9
857	N	CF 3	0	O	Cyclo-C 6 H 11
858	N	CF 3	0	O	CH 2 CH═C(CH 3 ) 2
859	N	CF 3	0	O	CH 2 CH 2 CH═CH 2
860	N	CF 3	0	O	CH 2 CH═CH 2
861	N	CF 3	0	O	(CH 2 ) 5 CH═CH 2
862	N	CF 3	0	O	CH 2 C≡CH
863	N	CF 3	0	O	CH 2 C≡CCH 2 CH 3
864	N	CF 3	0	O	CHFCF 3
865	N	CF 3	0	O	COOCH 2 CH 3
866	N	CF 3	0	O	CH 2 CH 2 OH
867	N	CF 3	0	O	CH 2 CH 2 OCH 3
868	N	CF 3	0	O	CH 2 COOC(CH 3 ) 3
869	N	CF 3	0	O	CH 2 SPh
870	N	CF 3	0	O	CH 2 CONHCH 3
871	N	CF 3	0	O	CH 2 CH(OH)CH 2 OH
872	N	CF 3	0	O	CHO
873	N	CF 3	0	O	COCH 3
874	N	CF 3	0	O	CH 2 OC 6 H 5
875	N	CF 3	0	O	COPh
876	N	CF 3	0	O	CF 2 CH 3
877	N	CF 3	0	O	CH 2 CN
878	N	CF 3	0	O	CH 2 CH 2 CN
879	N	CF 3	0	O	CH═CF 2
880	N	CF 3	0	O	2-Furyl
881	N	CF 3	0	O	OH
882	N	CF 3	0	O	OCH 3
883	N	CF 3	0	O	OCH 2 CH 3
884	N	CF 3	0	O	OCHF 2
885	N	CF 3	0	O	OCH 2 Ph
886	N	CF 3	0	O	NH 2
887	N	CF 3	0	O	NHCH 3
888	N	CF 3	0	O	NHCH 2 CH 3
889	N	CF 3	0	O	N(CH 2 CH 3 ) 2
890	N	CF 3	0	O	N(CH 2 CN) 2
891	N	CF 3	0	O	N(CH 3 ) 2
892	N	CF 3	0	O	NHCOCH 3
893	N	CF 3	0	O	NHCOCH 2 CH 3
894	N	CF 3	0	O	OSO 2 CH 3
895	N	CH 2 CH 2 Cl	0	O	CH 2 CH 3
896	N	CH 2 CH 2 Cl	0	O	NH 2
897	N	CH 2 Cl	0	O	CH 3
898	N	CHF 2	0	O	CH 3
899	N	CHF 2	0	O	CH 2 CH 3
900	N	CHF 2	0	O	CH(CH 3 )(CH 2 ) 4 CH 3
901	N	CHF 2	0	O	CH 2 CH═CH 2
902	N	CHF 2	0	O	COOCH 2 CH 3
903	N	CHF 2	0	O	NH 2
904	CH	CF 3	0	O	CH 3	60-61
905	CH	CF 3	1	O	CH 3
906	CH	CF 3	0	O	CH 2 CH 3	oil
907	CH	CF 3	1	O	CH 2 CH 3	oil
908	CH	CF 3	0	O	(CH 2 ) 2 CH 3	oil
909	CH	CF 3	1	O	(CH 2 ) 2 CH 3	oil
910	CH	CF 3	0	O	CH(CH 3 ) 2
911	CH	CF 3	1	O	CH(CH 3 ) 2
912	CH	CF 3	0	O	(CH 2 ) 3 CH 3
913	CH	CF 3	1	O	(CH 2 ) 3 CH 3
914	CH	CF 3	0	O	CH(CH 3 )CH 2 CH 3
915	CH	CF 3	1	O	CH(CH 3 )CH 2 CH 3
916	CH	CF 3	0	O	CH 2 CH(CH 3 ) 2
917	CH	CF 3	1	O	CH 2 CH(CH 3 ) 2
918	CH	CF 3	0	O	C(CH 3 ) 3
919	CH	CF 3	1	O	C(CH 3 ) 3
920	CH	CF 3	0	O	(CH 2 ) 4 CH 3
921	CH	CF 3	1	O	(CH 2 ) 4 CH 3
922	CH	CF 3	0	O	CH(CH 3 )(CH 2 ) 2 CH 3
923	CH	CF 3	0	O	(CH 2 ) 2 CH(CH 3 ) 2
924	CH	CF 3	0	O	CH 2 C(CH 3 ) 3
925	CH	CF 3	0	O	cyclo-C 5 H 9
926	CH	CF 3	0	O	cyclo-C 6 H 11
927	CH	CF 3	0	O	CH 2 (3-Thienyl)	oil
928	CH	CF 3	0	O	CHO
929	CH	CF 3	0	O	CH═CH 2
930	CH	CF 3	0	O	CH 2 Ph	61-63
931	CH	CF 3	0	O	CH 2 CH═C(CH 3 ) 2
932	CH	CF 3	0	O	CH 2 CH═CH 2
933	CH	CF 3	0	O	C(CH 3 )═CH 2
934	CH	CF 3	0	O	(CH 2 ) 5 C═CH 2
935	CH	CF 3	0	O	C(═CHCH 3 )CH 3
936	CH	CF 3	0	O	CH 2 C≡CH
937	CH	CF 3	0	O	CH 2 CH 2 C≡CH 2
938	CH	CF 3	0	O	CH 2 C≡CCH 2 CH 3
939	CH	CF 3	0	O	(CH 2 ) 4 C≡CH
940	CH	CF 3	0	O	CHFCF 3
941	CH	CF 3	0	O	COOCH 2 CH 3
942	CH	CF 3	0	O	CH 2 CH 2 OH
943	CH	CF 3	0	O	CH 2 CH 2 OCH 3
944	CH	CF 3	0	O	CH 2 COOC(CH 3 ) 3
945	CH	CF 3	0	O	CH 2 SPh
946	CH	CF 3	0	O	CH 2 CONHCH 3
947	CH	CF 3	0	O	CH 2 CH(OH)CH 2 OH
948	CH	CF 3	0	O	CH 2 COCH 3
949	CH	CF 3	0	O	COCH3
950	CH	CF 3	0	O	CH 2 Oph
951	CH	CF 3	0	O	COPh
952	CH	CF 3	0	O	CF 2 CH 3
953	CH	CF 3	0	O	CH 2 CN	oil
954	CH	CF 3	0	O	CH 2 CH(—O—)CH 2
955	CH	CF 3	0	O	CH 2 (4-OCH 3 )Ph
956	CH	CF 3	0	O	CH 2 CH(OH)CH 2 SPh
957	CH	CF 3	0	O	CH═CF 2
958	CH	CF 3	0	O	CCl═CHCl
959	CH	CF 3	0	O	Ph	120-121
960	CH	CF 3	0	O	2-Thienyl	87-89
961	CH	CF 3	0	O	OPh
962	CH	CF 3	0	O	OH
963	CH	CF 3	0	O	OCH 3
964	CH	CF 3	0	O	OCH 2 CH 3
965	CH	CF 3	0	O	OCHF 2
966	CH	CF 3	0	O	OCH 2 Ph
967	CH	CF 3	0	O	SCH 3
968	CH	CF 3	0	O	SPh
969	CH	CF 3	0	O	NH 2	190-191
970	CH	CF 3	0	O	NHCH 3
971	CH	CF 3	0	O	NHCH 2 CH 3
972	CH	CF 3	0	O	N(CH 2 CH 3 ) 2
973	CH	CF 3	0	O	N(CH 2 CN) 2
974	CH	CF 3	0	O	N(CH 3 ) 2
975	CH	CF 3	0	O	NHCOCH 3
976	CH	CF 3	0	O	NHCOCH 2 CH 3
977	CH	CF 3	0	O	OSO 2 CH 3
978	CH	CF 3	0	O	SOCH 2 (4-Br)—C 6 H 4
979	CH	CF 3	0	O	N(CH 3 )COOCH 2 Ph
980	CH	CF 3	0	NCH 3	CH 3
981	CH	CF 3	0	NCH 2 CH 3	CH 3
982	CH	CF 3	0	NCH 2 CH 3	CH 2 CH 3
983	CH	CF 3	0	NCH 2 CN	CH 2 CH 3
984	CH	CF 3	0	NCH 2 OCH 3	NHCH 3
985	CH	CF 3	0	NCH 2 OCH 2 CH 3	CN
986	CH	CF 3	0	NCH 2 CH═CH 2	CH 3
987	CH	CF 3	0	NCH 2 CH═CF 2	SCH 3
988	CH	CF 3	0	NCH 2 OCH 3	SCH 2 CH 3
989	CH	CF 3	0	NCH 2 OCH 3	SCH 2 Ph
990	CH	CHF 2	0	O	CH 3
991	CH	CHF 2	0	O	CH 2 CH 3
992	CH	CHF 2	0	O	(CH 2 ) 2 CH 3
993	CH	CHF 2	0	O	CH 2 CH═CH 2
994	CH	CHF 2	0	O	C(CH 3 )═CH 2
995	CH	CHF 2	0	O	COOCH 2 CH 3
996	CH	CHF 2	0	O	CH 2 CONHCH 3
997	CH	CHF 2	0	O	CF 2 CH 3
998	CH	CHF 2	0	O	CHO
999	CH	CHF 2	0	O	NH 2
1000	CH	CHF 2	0	O	NHCOCH 3
1001	N	CF 2 CF 3	0	S	CH 3
1002	N	CF 2 CF 3	0	S	CH 2 CH 3
1003	N	CF 2 CF 3	0	S	(CH 2 ) 2 CH 3
1004	N	CF 3	0	S	CH 3
1005	N	CF 3	0	S	CH 2 CH 3
1006	N	CF 3	0	S	(CH 2 ) 2 CH 3
1007	N	CF 3	0	S	CHFCF 3
1008	N	CF 3	0	S	CH 2 CH 2 OH
1009	N	CF 3	0	S	CH 2 COOC(CH 3 ) 3
1010	CH	CF 3	0	S	CH 3
1011	CH	CF 3	0	S	CH 2 CH 3
1012	CH	CF 3	0	S	(CH 2 ) 2 CH 3
1013	CH	CF 3	0	S	CHO
1014	CH	CF 3	0	S	CHFCF 3
1015	CH	CF 3	0	S	CH 2 C≡CH
1016	CH	CF 3	0	S	COOCH 2 CH 3
1017	CH	CF 3	0	S	CH 2 COOC(CH 3 ) 3
1018	CH	CF 3	0	S	CH 2 CN

TABLE 4
							m.p.
No.	X	Y	m	V	R 2	R 3	[° C.]
1019	N	(CF 2 ) 3 CHF 2	0	S	H	CH 2 CH 3
1020	N	CF 2 CF 2 CF 3	0	S	H	CH 2 CH 3
1021	N	CF 2 CF 3	0	S	H	CH 2 CH 3
1022	N	CH 2 CH 2 Cl	0	S	H	CH 2 CH 3
1023	N	CH 2 Cl	0	S	H	CH 2 CH 3
1024	N	CF 3	0	S	CH 2 CH 3	CH 2 CH 3
1025	N	CF 3	0	S	(CH 2 ) 2 CH 3	H
1026	N	CF 3	0	S	CH(CH 3 ) 2	H
1027	N	CF 3	0	S	CH 2 CH(CH 3 ) 2	H
1028	N	CF 3	0	S	C(CH 3 ) 3	H
1029	CH	CF 3	0	S	H	CH 3	oil
1030	CH	CF 3	0	S	H	CH 2 CH 3	oil
1031	CH	CF 3	0	S	H	C(CH 3 ) 3	oil
1032	CH	CF 3	0	S	CH 2 CH 3	COOCH 2 CH 3
1033	CH	CF 3	0	S	(CH 2 ) 2 CH 3	COOCH 2 CH 3
1034	CH	CF 3	0	S	CH(CH 3 ) 2	COOCH 2 CH 3
1035	CH	CF 3	0	S	CH(CH 3 ) 2	CONHCH 2 CH 3
1036	CH	CF 3	0	S	CH(CH 3 ) 2	CONHCH 2 CH 3
1037	CH	CF 3	0	S	CH(CH 3 ) 2	CON(CH 2 CH 3 ) 2
1038	CH	CF 3	0	S	CH(CH 3 ) 2	CONH-cyclo-C 3 H 7
1039	CH	CF 3	0	S	C(CH 3 ) 3	COOCH 2 CH 3
1040	CH	CF 3	0	S	H	CONHCH 2 CH 3
1041	CH	CF 3	0	S	H	CON(CH 2 CH 3 ) 2
1042	CH	CF 3	0	S	H	COOCH 2 CH 3	oil
1043	CH	CF 3	0	S	H	CH 2 COOCH 2 CH 3	oil
1044	CH	CF 3	0	S	H	CH 2 CHO
1045	CH	CF 3	0	S	H	CH 2 OCH 3
1046	CH	CF 3	0	S	H	CH 2 OCH 2 Ph
1047	CH	CF 3	0	S	H	H
1048	CH	CF 3	0	S	Cyclo-C 5 H 9	H
1049	CH	CF 3	0	S	CON(CH 3 ) 2	CH 3	oil
1050	CH	CF 3	0	S	CH 3	CH 2 CH 2 OH
1051	CH	CF 3	0	S	CH 3	CH 2 CH 2 OCH 3
1052	CH	CF 3	0	S	CH 3	CH 2 CH 2 OCH 2 Ph
1053	CH	CF 3	0	S	CH 3	CH 2 CH 2 SPh
1054	CH	CF 3	0	S	CH 3	CH 3	oil
1055	CH	CF 3	0	S	CH 3	CH 2 CH 2 CHO
1055	CH	CF 3	0	S	CH 3	CH 2 CH 2 CHNPh
1057	CH	CF 3	0	S	CH 3	CH 2 CH 2 CONH 2
1058	CH	CF 3	0	S	H	(4-CF 3 O)C 6 H 4	120-121
1059	CH	CF 3	0	S	CH 2 C≡CH	H
1060	CH	CF 3	0	S	CH 2 CH 2 C≡CH	H
1061	CH	CF 3	0	S	CH 2 C≡CCH 2 CH 3	H
1062	CH	CF 3	0	S	CH 2 CH═C(CH 3 ) 2	H
1063	CH	CF 3	0	S	CH 2 CH 2 CH═CH 2	H
1064	CH	CF 3	0	S	CH 2 CH═CH 2	H
1065	CH	CF 3	0	S	C(CH 3 )═CH 2	H
1066	CH	CF 3	0	S	CHFCF 3	H
1067	CH	CF 3	0	S	COOCH 2 CH 3	H
1068	CH	CF 3	0	S	CH 2 CH 2 OH	H
1069	CH	CF 3	0	S	CH 2 CH 2 OCH 3	H
1070	CH	CF 3	0	S	CH 2 COOC(CH 3 ) 3	H
1071	CH	CF 3	0	S	CH 2 COCH 3	H
1072	CH	CF 3	0	S	COCH3	H
1073	CH	CF 3	0	S	CH 2 Oph	H
1074	CH	CF 3	0	S	COPh	H
1075	CH	CF 3	0	S	CO(4-Cl)—C 6 H 4	H
1076	CH	CF 3	0	S	CF 2 CH 3	H
1077	CH	CF 3	0	S	CH 2 CN	H
1078	CH	CF 3	0	S	CH 2 CH 2 CN	H
1079	N	CF 3	0	S	H	H
1080	N	CF 3	0	S	H	CH 2 CH 2 CN
1081	N	CF 3	0	S	H	CH 2 CO 2 C(CH 3 ) 3
1082	N	CF 3	0	S	H	CH 2 CHO
1083	N	CF 3	0	S	H	CH 2 CH 2 OH
1084	N	CF 3	0	S	H	CH 2 CH 2 OCH 3
1085	N	CF 3	0	S	Cyclo-C 5 H 9	H
1086	N	CF 3	0	S	CH 3	COOCH 2 CH 3
1087	N	CF 3	0	S	CH 3	COOH
1088	N	CF 3	0	S	CH 3	CONH 2
1089	N	CF 3	0	S	CH 3	CONHCH 2 CH 3
1090	N	CF 3	0	S	CH 3	CON(CH 2 CH 3 ) 2
1091	N	CF 3	0	S	CH 3	CONHCH 3
1092	N	CF 3	0	S	CH 3	CONHCH 2 CN
1093	N	CF 3	0	S	CH 3	CON(CH 2 CN) 2
1094	N	CF 3	0	S	CH 3	CON(CH 3 ) 2
1095	N	CF 3	0	S	CH 2 C≡CH	OCH 2 CH 3
1096	N	CF 3	0	S	CH 2 CH 2 C≡CH	OCH 2 CH 3
1097	N	CF 3	0	S	CH 2 C≡CCH 2 CH 3	OCH 2 CH 3
1098	N	CF 3	0	S	CH 2 CH═C(CH 3 ) 2	OCH 2 CH 3
1099	N	CF 3	0	S	CH 2 CH 2 CH═CH 2	OCH 2 CH 3
1100	N	CF 3	0	S	CH 2 CH═CH 2	OCH 2 CH 3
1101	N	CF 3	0	S	C(CH 3 )═CH 2	OCH 2 CH 3
1102	N	CF 3	0	S	CHFCF 3	OCH 2 CH 3
1103	N	CF 3	0	S	COOCH 2 CH 3	OCH 2 CH 3
1104	N	CF 3	0	S	CH 2 CH 2 OH	OCH 2 CH 3
1105	N	CF 3	0	S	CH 2 CH 2 OCH 3	OCH 2 CH 3
1106	N	CF 3	0	S	CH 2 COOC(CH 3 ) 3	OCH 2 CH 3
1107	N	CF 3	0	S	CH 2 COCH 3	H
1108	N	CF 3	0	S	COCH3	H
1109	N	CF 3	0	S	CH 2 Oph	H
1110	N	CF 3	0	S	COPh	H
1111	N	CF 3	0	S	CO(4-Cl)—C 6 H 4	H
1112	N	CF 3	0	S	CF 2 CH 3	H
1113	N	CF 3	0	S	CH 2 CN	H
1114	N	CF 3	0	S	CH 2 CH 2 CN	H
1115	CH	CF 3	0	O	CH 2 CH 3	CH 2 CH 3
1116	CH	CF 3	0	O	(CH 2 ) 2 CH 3	H
1117	CH	CF 3	0	O	H	CH 2 CH 3	oil
1118	CH	CF 3	0	O	CH(CH 3 ) 2	COOCH 2 CH 3
1119	CH	CF 3	0	O	CH(CH 3 ) 2	COOH
1120	CH	CF 3	0	O	CH(CH 3 ) 2	CONH 2
1121	CH	CF 3	0	O	CH(CH 3 ) 2	CH 3
1122	CH	CF 3	0	O	C(CH 3 ) 3	H
1123	CH	CF 3	0	O	H	CH 3
1124	CH	CF 3	0	O	H	cyclo-C 5 H 9
1125	CH	CF 3	0	O	H	CH 2 CH 2 CH 3
1126	CH	CF 3	0	O	H	Ph	103-1041
1127	CH	CF 3	0	O	H	2-Pyridyl
1128	CH	CF 3	0	O	H	2-Furyl
1129	CH	CF 3	0	O	Cyclo-C 5 H 9	H
1130	CH	CF 3	0	O	CH 3	COOCH 2 CH 3
1131	CH	CF 3	0	O	CH 3	COOH
1132	CH	CF 3	0	O	CH 3	CONH 2
1133	CH	CF 3	0	O	CH 3	CONHCH 2 CH 3
1134	CH	CF 3	0	O	CH 3	CON(CH 2 CH 3 ) 2
1135	CH	CF 3	0	O	CH 3	CONHCH 3
1136	CH	CF 3	0	O	CH 3	CONHCH 2 CN
1137	CH	CF 3	0	O	CH 3	CON(CH 2 CN) 2
1138	CH	CF 3	0	O	CH 3	CON(CH 3 ) 2
1139	CH	CF 3	0	O	CH 2 C≡CH	H
1140	CH	CF 3	0	O	CH 2 CH 2 C≡CH	H
1141	CH	CF 3	0	O	CH 2 C≡CCH 2 CH 3	H
1142	CH	CF 3	0	O	CH 2 CH═C(CH 3 ) 2	H
1143	CH	CF 3	0	O	CH 2 CH 2 C═CH	H
1144	CH	CF 3	0	O	CH 2 CH═CH 2	H
1145	CH	CF 3	0	O	C(CH 3 )═CH 2	H
1146	CH	CF 3	0	O	CHFCF 3	H
1147	CH	CF 3	0	O	COOCH 2 CH 3	H
1148	CH	CF 3	0	O	CH 2 CH 2 OH	H
1149	CH	CF 3	0	O	CH 2 CH 2 OCH 3	H
1150	CH	CF 3	0	O	CH 2 COOC(CH 3 ) 3	H
1151	CH	CF 3	0	O	CH 2 COCH 3	H
1152	CH	CF 3	0	O	COCH3	H
1153	CH	CF 3	0	O	CH 2 Oph	H
1154	CH	CF 3	0	O	COPh	H
1155	CH	CF 3	0	O	CO(4-Cl)—C 6 H 4	H
1156	CH	CF 3	0	O	CF 2 CH 3	H
1157	CH	CF 3	0	O	CH 2 CN	H
1158	CH	CF 3	0	O	CH 2 CH 2 CN	H
1159	N	CF 3	0	O	CH 2 CH 3	CH 2 CH 3
1160	N	CF 3	0	O	(CH 2 ) 2 CH 3	H
1161	N	CF 3	0	O	CH(CH 3 ) 2	CONH 2
1162	N	CF 3	0	O	CH(CH 3 ) 2	CH 3
1163	N	CF 3	0	O	C(CH 3 ) 3	H
1164	N	CF 3	0	O	H	CH 3
1165	N	CF 3	0	O	H	CH 2 CH 3
1166	N	CF 3	0	O	H	CH 2 CH 2 CH 3
1167	N	CF 3	0	O	H	Ph
1168	N	CF 3	0	O	H	2-Pyridyl
1169	N	CF 3	0	O	H	2-Furyl
1170	N	CF 3	0	O	Cyclo-C 5 H 9	H
1171	N	CF 3	0	O	CH 3	COOCH 2 CH 3
1172	N	CF 3	0	O	CH 3	COOH
1173	N	CF 3	0	O	CH 3	CONH 2
1174	N	CF 3	0	O	CH 3	CONHCH 2 CH 3
1175	N	CF 3	0	O	CH 3	CON(CH 2 CH 3 ) 2
1176	N	CF 3	0	O	CH 3	CONHCH 3
1177	N	CF 3	0	O	CH 3	CONHCH 2 CN
1178	N	CF 3	0	O	CH 3	CON(CH 2 CN) 2
1179	N	CF 3	0	O	CH 3	CON(CH 3 ) 2
1180	N	CF 3	0	O	CH 2 C≡CH	H
1181	N	CF 3	0	O	CH 2 CH 2 C≡CH	H
1182	N	CF 3	0	O	CH 2 C≡CCH 2 CH 3	H
1183	N	CF 3	0	O	CH 2 CH═C(CH 3 ) 2	H
1184	N	CF 3	0	O	CH 2 CH 2 CH═CH 2	H
1185	N	CF 3	0	O	CH 2 CH═CH 2	H
1186	N	CF 3	0	O	C(CH 3 )═CH 2	H
1187	N	CF 3	0	O	CHFCF 3	H
1188	N	CF 3	0	O	COOCH 2 CH 3	H
1189	N	CF 3	0	O	CH 2 CH 2 OH	H
1190	N	CF 3	0	O	CH 2 CH 2 OCH 3	H
1191	N	CF 3	0	O	CH 2 COOC(CH 3 ) 3	H
1192	N	CF 3	0	O	CH 2 COCH 3	H
1193	N	CF 3	0	O	COCH3	H
1194	N	CF 3	0	O	OCH 2 Oph	H
1195	N	CF 3	0	O	COPh	H
1196	N	CF 3	0	O	CO(4-Cl)—C 6 H 4	H
1197	N	CF 3	0	O	CF 2 CH 3	H
1198	N	CF 3	0	O	CH 2 CN	H
1199	N	CF 3	0	O	CH 2 CH 2 CN	H
1200	N	CF 3	0	O	CH 2 NHSO 2 CH 3	CH 3
1201	N	CF 3	0	O	(CH 2 ) 2 NHSO 2 CH 3	CH 3
1202	N	CF 3	0	O	CH 2 NHSO 2 CH 2 CH 3	CH 3
1203	N	CF 3	0	O	H	CH 2 NHSO 2 CH 2 Ph
1204	CH	CF 3	0	O	(CH 2 ) 4 NHSO 2 CF 3	CH 3
1205	CH	CF 3	0	O	(CH 2 ) 2 S(CH 2 ) 2 CH 3	CH 2 CH 2 CH 3
1206	CH	CF 3	0	O	(CH 2 ) 4 S(CH 2 ) 4 0CH 3	CH 3
1207	CH	CF 3	0	S	CH 3	(CH 2 ) 2 S(CH 2 ) 2 CN
1208	CH	CF 3	0	S	CH 2 NHSO 2 CH 2 CH 3	CH 3
1209	CH	CF 3	0	S	CH 2 NHSO 2 CH 2 Ph	CH 2 CH 2 CH 3
1210	CH	CF 3	0	S	(CH 2 ) 2 NHSO 2 CH 3	CF 3
1211	CH	CF 3	0	S	H	CH 2 NHSO 2 CH 3
1212	CH	CF 3	0	S	CH(CH 3 )CH 2 NHPh	CF 3
1213	CH	CF 3	0	S	(CH 2 ) 2 S(2-F)—C 6 H 4	CH 2 CH 2 CH 3
1214	CH	CF 3	0	S	(CH 2 ) 6 NHCH 2 ) 6 OCH 3	CF 3
1215	CH	CF 3	0	S	H	(CH 2 ) 2 NH—(2-F)—C 6 H 4
1216	CH	CF 3	0	S	(CH 2 ) 3 NHCH 2 CN	H
1217	CH	CF 3	0	S	(CH 2 ) 2 O(3-Cl)—C 6 H 4	CH 3
1218	CH	CF 3	0	S	CF 3	(CH 2 ) 6 NHCH 2 CF 3
1219	CH	CF 3	0	S	CH 3	(CH 2 ) 2 O(3-CH 3 )—C 6 H 4
1220	CH	CF 3	0	O	H	CH 2 NHPh
1221	CH	CF 3	0	O	CH 3	(CH 2 ) 4 S(2-Br)—C 6 H 4
1222	CH	CF 3	0	O	(CH 2 ) 6 NH(CH 2 ) 2 OCH 3	CH 3
1223	CH	CF 3	0	O	(CH 2 ) 2 NH(CH 2 ) 4 OCH 3	H
1224	CH	CF 3	0	O	CF 3	(CH 2 ) 3 NH—(4-CN)—C 6 H 4
1225	CH	CF 3	0	O	(CH 2 ) 4 NHCH 2 CF 3	CH 3
1226	CH	CF 3	0	O	C 2 F 5	(CH 2 ) 2 O(3-CH 3 )—C 6 H 4
1227	CH	CF 3	0	O	(CH 2 ) 4 NHCH 2 CN	H
1228	CH	CF 3	0	O	(CH 2 ) 3 O(4-Cl)—C 6 H 4	C 2 F 5

TABLE 5
								m.p.
No.	X	Y	V	R 4	R 5	R 6	R 7	[° C.]
1229	CH	CF 3	O	H	H	H	H	oil
1230	CH	CF 3	O	H	H	CH 3	H	oil
1231	CH	CF 3	O	H	H	CH 2 CH 3	H	oil
1232	CH	CF 3	O	H	H	CH(CH 3 ) 2	H
1233	CH	CF 3	O	H	H	CH 2 CH(CH 3 ) 2	H
1234	CH	CF 3	O	H	H	CH(CH 3 )CH 2 CH 3	H
1235	CH	CF 3	O	H	H	CH 2 OH	H
1236	CH	CF 3	O	H	H	CH(OH)CH 3	H
1237	CH	CF 3	O	H	H	CH 2 SH	H
1238	CH	CF 3	O	H	H	CH 2 CH 2 SCH 3	H
1239	CH	CF 3	O	H	H	(CH 2 ) 3 NH 2	H
1240	CH	CF 3	O	H	H	(CH 2 ) 4 NH 2	H
1241	CH	CF 3	O	H	H	CH═CH 2	H
1242	CH	CF 3	O	H	H	(CH 2 ) 2 COOCH 3	H
1243	CH	CF 3	O	H	H	(CH 2 ) 2 COOH	H
1244	CH	CF 3	O	H	H	(CH 2 ) 2 CONH 2	H
1245	CH	CF 3	S	CH 3	CH 3	H	H
1246	CH	CF 3	O	H	H	CH 3	CH 3	oil
1247	CH	CF 3	O	H	H	CH 2 COOCH 3	H
1248	CH	CF 3	O	H	H	CH 2 COOH	H
1249	CH	CF 3	O	H	H	CH 2 CONH 2	H
1250	CH	CF 3	O	H	H	CH 2 Ph	H
1251	CH	CF 3	O	H	H	CH 2 —(4-OH)—C 6 H 4	H
1252	CH	CF 3	O	H	H	CH 2 —(3-Indolyl)	H
1253	CH	CF 3	O	CH 3	CH 3	H	H	oil
1254	CH	CF 3	O	CH 3	H	H	H	oil
1255	CH	CF 3	O	CH 3	H	H	Ph
1256	CH	CF 3	O	H		(CH 2 ) 4	H
1257	CH	CF 3	NH	H		(CH 2 ) 4	H
1258	CH	CF 3	NCH 3	H		(CH 2 ) 4	H
1259	CH	CF 3	NCH 2 C 6 H 4	H		(CH 2 ) 4	H
1260	CH	CF 3	NCH(CH 3 ) 2	H		(CH 2 ) 4	H
1261	CH	CF 3	O	Ph	H	Ph	H
1262	CH	CF 3	NH	Ph	H	Ph	H
1263	CH	CF 3	NCH 3	Ph	H	Ph	H
1264	CH	CF 3	NCH 2 C 6 H 4	Ph	H	Ph	H
1265	N	CF 3	O	H	H	CH 2 CH 3	H	oil
1266	N	CF 3	O	H	H	CH(CH 3 ) 2	H
1267	N	CF 3	O	H	H	CH 2 CH(CH 3 ) 2	H
1268	N	CF 3	O	H	H	CH 2 COOH	H
1269	N	CF 3	O	H	H	CH 2 COOCH 3	H
1270	N	CF 3	O	H	H	CH 2 CONH 2	H
1271	N	CF 3	O	CH 3	CH 3	H	H
1272	N	CF 3	O	H	(CH 2		H
1273	N	CF 3	O	H	H	CH 2 CH 2 SCH 3	H
1274	CH	CF 3	S	H	H	H	H	oil

TABLE 6
					m.p.
No.	X	Y	R 8	R 1	[° C.]
1275	CH	CF 3	CH 3	SH	209-210
1276	CH	CF 3	CH 3	SCH 3
1277	CH	CF 3	CH 3	SCH 2 CH 3
1278	CH	CF 3	CH 3	S(CH 2 ) 2 CH 3
1279	CH	CF 3	CH 3	SCH(CH 3 ) 2
1280	CH	CF 3	CH 3	SPh
1281	CH	CF 3	CH 3	S(CH 2 ) 3 CH 3
1282	CH	CF 3	CH 3	SCH(CH 3 )CH 2 CH 3
1283	CH	CF 3	CH 3	SCH 2 CH(CH 3 ) 2
1284	CH	CF 3	CH 3	OH	119-120
1285	CH	CF 3	CH 3	OCH 3
1286	CH	CF 3	CH 3	OCH 2 CH 3
1287	CH	CF 3	CH 3	OCHF 2
1288	CH	CF 3	CH 3	OCH 2 Ph
1289	CH	CF 3	CH 3	OCONHPh
1290	CH	CF 3	CH 3	OCONH—(4-F)—C 6 H 4
1291	CH	CF 3	CH 3	OCONH—(3,5-di-Cl)—C 6 H 3
1292	CH	CF 3	CH 2 CN	OCH 3
1293	CH	CF 3	CH 2 CN	OCH 2 CH 3
1294	CH	CF 3	CH 2 CN	OCHF 2
1295	CH	CF 3	CH 2 CN	OCH 2 Ph
1296	CH	CF 3	CH 2 CN	OCONHPh
1297	CH	CF 3	CH 2 CN	OCONH—(4-F)—C 6 H 4
1298	CH	CF 3	CH 2 OCH 2 CH 3	OCH 3
1299	CH	CF 3	CH 2 OCH 2 CH 3	OCH 2 CH 3
1300	CH	CF 3	CH 2 OCH 2 CH 3	OCHF 2
1301	CH	CF 3	CH 2 OCH 2 CH 3	OCH 2 Ph
1302	CH	CF 3	CH 2 OCH 2 CH 3	OCONHPh
1303	CH	CF 3	H	CH 3	203-204
1304	CH	CF 3	H	CH 2 CH 3	134-135
1305	CH	CF 3	H	(CH 2 ) 2 CH 3
1306	CH	CF 3	H	CH(CH 3 ) 2
1307	CH	CF 3	H	Cyclo-C 3 H 5
1308	CH	CF 3	H	(CH 2 ) 3 CH 3
1309	CH	CF 3	H	CH(CH 3 )CH 2 CH 3
1310	CH	CF 3	H	CH 2 CH(CH 3 ) 2
1311	CH	CF 3	H	CH═CH 2
1312	CH	CF 3	H	CH 2 CH═C(CH 3 ) 2
1313	CH	CF 3	H	CH 2 CH 2 CH═CH 2
1314	CH	CF 3	H	CH 2 CH═CH 2
1315	CH	CF 3	H	C(CH 3 )═CH 2
1316	CH	CF 3	H	CHFCF 3
1317	CH	CF 3	H	COOCH 2 CH 3
1318	CH	CF 3	H	CH 2 CH 2 OH
1319	CH	CF 3	H	CH 2 CH 2 OCH 3
1320	CH	CF 3	H	CH 2 COOC(CH 3 ) 3
1321	CH	CF 3	CH 3	CH 2 COOC(CH 3 ) 3
1322	CH	CF 3	CH 2 CN	CH 2 COOC(CH 3 ) 3
1323	CH	CF 3	CH 2 OCH 2 CH 3	CH 2 COOC(CH 3 ) 3
1324	CH	CF 3	H	CH 2 SPh
1325	CH	CF 3	H	CH 2 CONHCH 3
1326	CH	CF 3	H	CH 2 COCH 3
1327	CH	CF 3	H	COCH3
1328	CH	CF 3	H	CH 2 Oph
1329	CH	CF 3	H	COPh
1330	CH	CF 3	H	CO(3-Cl)—C 6 H 4
1331	CH	CF 3	H	CF 2 CH 3
1332	CH	CF 3	H	CH 2 CN
1333	CH	CF 3	H	CH 2 CH 2 CN
1334	CH	CF 3	H	CH 2 CH(—O—)CH 2
1336	CH	CF 3	H	CH 2 (4-OCH 3 )Ph
1337	N	CF 3	CH 3	SH
1338	N	CF 3	CH 3	SCH 3
1339	N	CF 3	CH 3	SCH 2 CH 3
1340	N	CF 3	CH 3	SPh
1341	N	CF 3	CH 3	SCH 2 CH(CH 3 ) 2
1342	N	CF 3	CH 3	OH
1343	N	CF 3	CH 3	OCH 3
1344	N	CF 3	CH 3	OCH 2 CH 3
1345	N	CF 3	CH 3	OCH 2 Ph
1346	N	CF 3	CH 3	OCONHPh
1347	N	CF 3	CH 2 CN	OCH 3
1348	N	CF 3	CH 2 CN	OCH 2 CH 3
1349	N	CF 3	CH 2 CN	OCH 2 Ph
1350	N	CF 3	CH 2 CN	OCONHPh
1351	N	CF 3	CH 2 OCH 2 CH 3	OCH 3
1352	N	CF 3	CH 2 OCH 2 CH 3	OCH 2 Ph
1353	N	CF 3	CH 2 OCH 2 CH 3	OCONHPh
1354	N	CF 3	H	CH 3
1355	N	CF 3	H	CH 2 CH 3
1356	N	CF 3	H	(CH 2 ) 2 CH 3
1357	N	CF 3	H	CH(CH 3 ) 2
1358	N	CF 3	H	(CH 2 ) 3 CH 3
1359	N	CF 3	H	CH(CH 3 )CH 2 CH 3
1360	N	CF 3	H	CH 2 CH(CH 3 ) 2
1361	N	CF 3	H	CH 2 C═C(CH 3 ) 2
1362	N	CF 3	H	CH 2 CH═CH 2
1363	N	CF 3	H	C(CH 3 )H═CH 2
1364	N	CF 3	H	COOCH 2 CH 3
1365	N	CF 3	H	CH 2 CH 2 OH
1366	N	CF 3	H	CH 2 CH 2 OCH 3
1367	N	CF 3	H	CH 2 COOC(CH 3 ) 3
1368	N	CF 3	H	CH 2 SPh
1369	N	CF 3	H	CH 2 CONHCH 3
1370	N	CF 3	H	CH 2 COCH 3
1371	N	CF 3	H	COCH3
1372	N	CF 3	H	CH 2 Oph
1373	N	CF 3	H	COPh
1374	N	CF 3	H	CH 2 CN
1375	N	CF 3	H	CH 2 CH 2 CN
1376	CH	CF 3	CH 3	CH 2 CH 3	oil

C. Biological Examples

Example 1

A Petri dish whose bottom is covered with filter paper and which contains about 5 ml of culture medium is prepared. Pieces of filter paper with about 30, 24-hour-old eggs of the American tobacco budworm ( Heliothis virescens ) are dipped into an aqueous solution of the formulated preparation to be examined for 5 seconds and subsequently placed in the Petri dish. A further 200 μl of the aqueous solution are spread over the culture medium. The Petri dish is closed and then kept at about 25° C. in a climatized chamber. After 6 days' storage, the effect of the preparation on the eggs and the larvae which may have hatched from these is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Example Nos. 79 and 88 effect a mortality of 90-100%.

Example 2

Germinated broad bean seeds ( Vicia faba ) with radicles are transferred into brown glass bottles filled with tap water and subsequently populated with approximately 100 black bean aphids ( Aphis fabae ) belegt. Plants and aphids are then dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has dripped off, plant and animals are kept in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity. After 3 and 6 days' storage, the effect of the preparation on the aphids is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Example Nos. 79, 78, 80, 81, 83, 84, 88, 133, 135, 136, 137, 138, 139, 1117, 1229, 1230, 1231, 1246 and 1254 effect a mortality of 90-100% among the aphids.

Example 3

The leaves of 12 rice plants having a stem length of 8 cm are dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has dripped off, the rice plants treated in this manner are placed in a Petri dish and populated with approximately 20 larvae (L3 stage) of the rice leaf hopper species Nilaparvata lugens . The Petri dish is closed and stored in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity). After 6 days' storage, the mortality among the leaf hopper larvae is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Example Nos. 88, 139 and 927 effect a mortality of 90-100%.

Example 4

Germinated broad bean seeds ( Vicia faba ) with radicles are transferred into brown glass bottles filled with tap water. Four milliliters of an aqueous solution of the formulated preparation to be examined are pipetted into the brown glass bottle. The broad bean is subsequently heavily populated with approximately 100 black bean aphids ( Aphis fabae ). Plant and animals are then stored in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity). After 3 and 6 days' storage, the root-systemic activity of the preparation on the aphids is determined. At a concentration of of 30 ppm (based on the content of active compound), the Preparations of Example Nos. 78, 79, 80, 81, 83, 84, 88, 133, 135, 136, 137, 138, 139, 187, 1117, 1229, 1230, 1231, 1246 and 1254 effect a mortality of 90-100% among the aphids by root-systemic action.

II. COMPOUNDS OF THE FORMULA (I′)

A. Chemical Examples

Example 1

At room temperature, a solution of 4-tridiimidfluoromethylnicotinic acid (2.2 g) in 40 ml of THF was admixed with 1,1-carbonyldiimidazole (1.9 g), and the mixture was heated at 40° C. for 30 min. Furfurylsulfonylacetamidoxime (2.5 g) was then added, and the mixture was stirred at 40° C. for a further 5 h. The reaction mixture was then concentrated under reduced pressure and poured onto ice-water. The resulting precipitate was filtered off with suction and subsequently dried in a drying cabinet. This gave 4-trifluoromethylnicotinic acid furfurylsulfonylacetamidoxime ester in the form of a colorless solid (melting point 171° C.).

1 H-NMR (DMSO-d 6 , 300 MHz): 4.09 (s, 2H), 4.86 (s, 2H), 6.55 (m, 1H), 6.63 (m, 1H), 7.08 (s, 2H), 7.75 (m, 1H), 7.94 (d, J=5 Hz, 1H), 9.07 (d, J=5 Hz, 1H), 9.30 (s, 1H).

Example 2

The amidoxime ester described above (4.0 g) was admixed with 80 ml of toluene and 60 ml of xylene and Amberlyst 15 (1.0 g). The reaction mixture was heated at 125° C. for 6 h. The mixture was subsequently filtered off with suction and the filtrate was concentrated under reduced pressure and purified by chromatography (silica gel, ethyl acetate/petroleum ether, 4:1). Subsequent trituration with n-heptane gave [5-(4′-trifluoromethylpyridin-3′-yl)-[1,2,4]-oxadiazole-3-methyl]furfurylsulfone as a pale yellow solid (melting point 99° C.).

1 H-NMR (CDCl 3 , 300 MHz): 4.53 (s, 2H), 4.62 (s, 2H), 6.44 (m, 1H), 6.69 (m, 1H), 7.54 (m, 1H), 7.82 (d, J=5 Hz, 1H), 9.08 (d, J=5 Hz, 1H), 9.40 (s, 1H).

Example 3

A mixture of 3-chloromethyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole (1.0 g), sodium sulfite (0.9 g), water (18 ml) and methanol (18 ml) was stirred at 50° C. for 6 hours. The reaction mixture was then concentrated and the residue was taken up in methanol and filtered. The methanol solution was then concentrated and the residue was triturated with diethyl ether. This gave

as a slightly yellowish solid (m.p.=214° C.).

1 H-NMR (DMSO-d 6 , 300 MHz): 4.02 (s, 2H), 8.09 (d, J=5H, 1H), 9.15 (d, J=5 Hz, 1H), 9.33 (s, 1H).

The sodium sulfonate described above (0.95 g) was suspended in phosphorus oxychloride (30 ml), and the mixture was heated at reflux temperature for 5 hours. The excess phosphorus oxychloride was then distilled off and the sulfonyl chloride which remained was taken up in dichloromethane (10 ml). This suspension was admixed with ethylmethylamine (150 ml), and stirring at room temperature was continued for one hour.

The mixture was subsequently washed with water, 5% strength aqueous potassium hydrogen-sulfate solution and saturated sodium bicarbonate solution. The crude product which was obtained after drying (MgSO 4 ) and concentration of the dichloromethane phase was purified chromatographically. This gave the desired sulfonamide as a colorless oil.

1 H-NMR (CDCl 3 , 300 MHz): 1.23 (6, J=7 Hz, 3H), 2.92 (s, 3H), 3.25 (Q, J=7Hz, 2H), 4.54 (s, 2H), 7.90 (d, J=5 Hz, 1H), 9.06 (d, J=5 Hz, 1H), 9.35 (s, 1H).

The sulfonamides listed in Table 1 are prepared in an analogous manner.

Example 4

3-[(2-Hydroxyethyl)thiomethyl]-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

A solution of sodium methoxide (0.31 ml, 30% in methanol) was added to a solution of 3-chloromethyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole (0.5 g) and 2-mercaptoethanol (0.13 g) in methanol (5 ml), and the mixture was stirred at room temperature for 5 hours.

Water was then added and the mixture was extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO 4 ), filtered and concentrated. Chromatographic purification was carried out over silica gel using heptane/ethyl acetate. The crude product gave the desired compound as a slightly brown oil.

1 H-NMR (CDCl 3 , 300 MHz): 2.88 (t, J=7 Hz, 2H), 3.04 (b, s, 1H), 3.82 (t, J=7 Hz, 2H), 3.94 (s, 2H), 7.80 (d, J=5 Hz, 1H), 9.04 (d, J=5 Hz, 1H), 9.35 (s, 1H).

Example 5

3-Ethoxymethyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

3-Iodomethyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole (0.5 g) was dissolved in a freshly prepared solution of sodium ethoxide (30 mg of sodium in 7 ml of ethanol), and the mixture was stirred at room temperature for 6 hours.

The reaction mixture was then concentrated, the residue was taken up in ethyl acetate, washed with water, dried (MgSO 4 ), filtered and concentrated.

Chromatographic purification of the crude product gave the desired ether as a yellowish oil.

1 H-NMR (CDCl 3 , 300 MHz): 1.31 (t, J=7 Hz, 3H), 3.72 (t, J=7 Hz, 2H), 4.76 (s, 2H), 7.70 (d, J=5 Hz, 1H), 9.03 (d, J=5 Hz, 1H), 9.33 (s, 1H).

The ethers listed in Table 1 are prepared in an analogous manner.

Example 6

Ethyl [(4′-(Trifluoromethyl)pyridin-3′-yl)-5-[1,2,4]-oxadiazole-3-methyl]carbonate

3-Hydroxymethyl-5-(4′-(trifluoromethyl)pyridin-3′-yl)-[1,2,4]-oxadiazole (1.0 g) was initially charged in acetonitrile (10 ml), and the mixture was admixed with triethylamine (0.5 g). Ethyl chloroformate (0.5 g) was added, and the mixture was then stirred at room temperature for 6 h. The reaction mixture was then mixed with ethyl acetate (5 ml), washed with 2N sodium carbonate solution and dried over MgSO 4 . The crude product which was obtained after the drying agent had been filtered off and the solution had been concentrated under reduced pressure was purified by column chromatography (silica gel, n-heptane/ethyl acetate, 1:1). This gave the target product as an oil.

1 H-NMR (CDCl 3 , 300 MHz): 1.38 (t, J=7 Hz, 3H), 4.31 (q, J=7 Hz, 2H), 5.43 (s, 2H), 7.80 (d, J=5 Hz, 1H), 9.04 (d, J=5 Hz, 1H), 9.37 (s, 1H).

TABLE 1
Ex.				m.p.
No.	Y	R	R′	[° C.]
1	O	n-Pr
2	O	i-Pr
3	O	n-Bu
4	O	i-Bu		oil
5	O	allyl
6	O	CH 2 C≡CH
7	O	CH═CH 2
8	O	CH 2 CH 2 F
9	O	CF 3
10	O	CH 2 CF 3
11	O	CH 2 CN
12	O	cyclopropyl
13	O	cyclopropylmethyl
14	O	CH 2 CO 2 Me
15	O	CH 2 CH 2 NMe 2
16	O	CH 2 -(N-morpholinyl)
17	O	2-chloropyridin-5-yl-methyl
18	O	2-furanyl
19	O	2-pyrimidinyl
20	O	2-oxazolyl
21	O	5-[1,2,4]-oxadiazolyl
22	O	tetrazolyl
23	S	H
24	S	Me
25	S	Et
26	S	n-Pr
27	S	i-Pr
28	S	n-Bu
29	S	i-Bu
30	S	allyl
31	S	CH 2 C≡CH
32	S	CH═CH 2
33	S	CH 2 CH 2 F
34	S	CF 3
35	S	CH 2 CF 3
36	S	CH 2 CN
37	S	cyclopropyl
38	S	cyclopropylmethyl
39	S	CH 2 CO 2 Me
40	S	CH 2 CH 2 NMe 2
41	S	CH 2 -(N-morpholinyl)
42	S	2-chloropyridin-5-yl-methyl
43	S	2-furanyl
44	S	2-pyrimidinyl
45	S	2-oxazolyl
46	S	5-[1,2,4]-oxadiazolyl
47	S	tetrazolyl
48	S(O)	Me
49	S(O)	Et
50	S(O)	n-Pr
51	S(O)	i-Pr
52	S(O)	n-Bu
53	S(O)	i-Bu
54	S(O)	allyl
55	S(O)	CH 2 C≡CH
56	S(O)	CH═CH 2
57	S(O)	CH 2 CH 2 F
58	S(O)	CF 3
59	S(O)	CH 2 CF 3
60	S(O)	CH 2 CN
61	S(O)	cyclopropyl
62	S(O)	cyclopropylmethyl
63	S(O)	CH 2 CO 2 Me
64	S(O)	CH 2 CH 2 NMe 2
65	S(O)	CH 2 -(N-morpholinyl)
66	S(O)	2-chloropyridin-5-yl-methyl
67	S(O)	2-furanyl
68	S(O)	2-pyrimidinyl
69	S(O)	2-oxazolyl
70	S(O)	5-[1,2,4]-oxadiazolyl
71	S(O)	tetrazolyl
72	S(O) 2	Me
73	S(O) 2	Et
74	S(O) 2	n-Pr
75	S(O) 2	i-Pr
76	S(O) 2	n-Bu
77	S(O) 2	i-Bu
78	S(O) 2	allyl
79	S(O) 2	CH 2 C≡CH
80	S(O) 2	CH═CH 2
81	S(O) 2	CH 2 CH 2 F
82	S(O) 2	CF 3
83	S(O) 2	CH 2 CF 3
84	S(O) 2	CH 2 CN
85	S(O) 2	cyclopropyl
86	S(O) 2	cyclopropylmethyl
87	S(O) 2	CH 2 CO 2 Me
88	S(O) 2	CH 2 CH 2 NMe 2
89	S(O) 2	CH 2 -(N-morpholinyl)
90	S(O) 2	2-chloropyridin-5-yl-methyl
91	S(O) 2	2-furanyl
92	S(O) 2	2-pyrimidinyl
93	S(O) 2	2-oxazolyl
94	S(O) 2	5-[1,2,4]-oxadiazolyl
94a	S(O) 2	tetrazolyl
95	OC(O)	H
96	OC(O)	Me
97	OC(O)	Et
98	OC(O)	n-Pr
99	OC(O)	i-Pr
100	OC(O)	n-Bu
101	OC(O)	i-Bu
102	OC(O)	allyl
103	OC(O)	CH 2 C≡CH
104	OC(O)	CH═CH 2
105	OC(O)	CH 2 CH 2 F
106	OC(O)	CF 3
107	OC(O)	CH 2 CF 3
108	OC(O)	CH 2 CN
109	OC(O)	cyclopropyl
110	OC(O)	cyclopropylmethyl
111	OC(O)	CH 2 CO 2 Me
112	OC(O)	CH 2 CH 2 NMe 2
113	OC(O)	CH 2 -(N-morpholinyl)
114	OC(O)	2-chloropyridin-5-yl-methyl
115	OC(O)	2-furanyl
116	OC(O)	2-pyrimidinyl
117	OC(O)	2-oxazolyl
118	OC(O)	5-[1,2,4]-oxadiazolyl
119	OC(O)	tetrazolyl
120	OC(O)O	Me
121	OC(O)O	Et
122	OC(O)O	n-Pr
123	OC(O)O	i-Pr
124	OC(O)O	n-Bu
125	OC(O)O	i-Bu
126	OC(O)O	allyl
127	OC(O)O	CH 2 C≡CH
128	OC(O)O	CH═CH 2
129	OC(O)O	CH 2 CH 2 F
130	OC(O)O	CF 3
131	OC(O)O	CH 2 CF 3
132	OC(O)O	CH 2 CN
133	OC(O)O	cyclopropyl
134	OC(O)O	cyclopropylmethyl
135	OC(O)O	CH 2 CO 2 Me
136	OC(O)O	CH 2 CH 2 NMe 2
137	OC(O)O	CH 2 -(N-morpholinyl)
138	OC(O)O	2-chloropyridin-5-yl-methyl
139	OC(O)O	2-furanyl
140	OC(O)O	2-pyrimidinyl
141	OC(O)O	2-oxazolyl
142	OC(O)O	5-[1,2,4]-oxadiazolyl
143	OC(O)O	tetrazolyl
144	OC(O)O	CH 2 CH 2 OMe
145	OC(O)NR′	H	H
146	OC(O)NR′	Me	H
147	OC(O)NR′	Et	H
148	OC(O)NR′	n-Pr	H
149	OC(O)NR′	i-Pr	H
150	OC(O)NR′	n-Bu	H
151	OC(O)NR′	i-Bu	H
152	OC(O)NR′	allyl	H
153	OC(O)NR′	CH 2 C≡CH	H
154	OC(O)NR′	CH═CH 2	H
155	OC(O)NR′	CH 2 CH 2 F	H
156	OC(O)NR′	CF 3	H
157	OC(O)NR″	CH 2 CF 3	H
158	OC(O)NR′	CH 2 CN	H
159	OC(O)NR′	cyclopropyl	H
160	OC(O)NR′	cyclopropylmethyl	H
161	OC(O)NR′	CH 2 CO 2 Me	H
162	OC(O)NR′	CH 2 CH 2 NMe 2	H
163	OC(O)NR′	CH 2 -(N-morpholinyl)	H
164	OC(O)NR′	2-chloropyridin-5-yl-methyl	H
165	OC(O)NR′	2-furanyl	H
166	OC(O)NR′	2-pyrimidinyl	H
167	OC(O)NR′	2-oxazolyl	H
168	OC(O)NR′	5-[1,2,4]-oxadiazolyl	H
169	OC(O)NR′	tetrazolyl	H
170	OC(O)NR′	H	Me
171	OC(O)NR′	Me	Me
172	OC(O)NR′	Et	Me
173	OC(O)NR′	n-Pr	Me
174	OC(O)NR′	i-Pr	Me
175	OC(O)NR′	n-Bu	Me
176	OC(O)NR′	i-Bu	Me
177	OC(O)NR′	allyl	Me
178	OC(O)NR′	CH 2 C≡CH	Me
179	OC(O)NR′	CH═CH 2	Me
180	OC(O)NR′	CH 2 CH 2 F	Me
181	OC(O)NR′	CF 3	Me
182	OC(O)NR″	CH 2 CF 3	Me
183	OC(O)NR′	CH 2 CN	Me
184	OC(O)NR′	cyclopropyl	Me
185	OC(O)NR′	cyclopropylmethyl	Me
186	OC(O)NR′	CH 2 CO 2 Me	Me
187	OC(O)NR′	CH 2 CH 2 NMe 2	Me
188	OC(O)NR′	CH 2 -(N-morpholinyl)	Me
189	OC(O)NR′	2-chloropyridin-5-yl-methyl	Me
190	OC(O)NR′	2-furanyl	Me
191	OC(O)NR′	2-pyrimidinyl	Me
192	OC(O)NR′	2-oxazolyl	Me
193	OC(O)NR′	5-[1,2,4]-oxadiazolyl	Me
194	OC(O)NR′	tetrazolyl	Me
195	OC(O)NR′	H	Et
196	OC(O)NR′	Me	Et
197	OC(O)NR′	Et	Et
198	OC(O)NR′	n-Pr	Et
199	OC(O)NR′	i-Pr	Et
200	OC(O)NR′	n-Bu	Et
201	OC(O)NR′	i-Bu	Et
202	OC(O)NR′	allyl	Et
203	OC(O)NR′	CH 2 C≡CH	Et
204	OC(O)NR′	CH═CH 2	Et
205	OC(O)NR′	CH 2 CH 2 F	Et
206	OC(O)NR′	CF 3	Et
207	OC(O)NR″	CH 2 CF 3	Et
208	OC(O)NR′	CH 2 CN	Et
209	OC(O)NR′	cyclopropyl	Et
210	OC(O)NR′	cyclopropylmethyl	Et
211	OC(O)NR′	CH 2 CO 2 Me	Et
212	OC(O)NR′	CH 2 CH 2 NMe 2	Et
213	OC(O)NR′	CH 2 -(N-morpholinyl)	Et
214	OC(O)NR′	2-chloropyridin-5-yl-methyl	Et
215	OC(O)NR′	2-furanyl	Et
216	OC(O)NR′	2-pyrimidinyl	Et
217	OC(O)NR′	2-oxazolyl	Et
218	OC(O)NR′	5-[1,2,4]-oxadiazolyl	Et
219	OC(O)NR′	tetrazolyl	Et
220	OC(O)C(O)O	H
221	OC(O)C(O)O	Me
222	OC(O)C(O)O	Et
223	OC(O)C(O)O	n-Pr
224	OC(O)C(O)O	i-Pr
225	OC(O)C(O)O	n-Bu
226	OC(O)C(O)O	i-Bu
227	OC(O)C(O)O	allyl
228	OC(O)C(O)O	CH 2 C≡CH
229	OC(O)C(O)O	CH═CH 2
230	OC(O)C(O)O	CH 2 CH 2 F
231	OC(O)C(O)O	CF 3
232	OC(O)C(O)O	CH 2 CF 3
234	OC(O)C(O)O	CH 2 CN
235	OC(O)C(O)O	cyclopropyl
236	OC(O)C(O)O	cyclopropylmethyl
237	OC(O)C(O)O	CH 2 CO 2 Me
238	OC(O)C(O)O	CH 2 CH 2 NMe 2
239	OC(O)C(O)O	CH 2 -(N-morpholinyl)
240	OC(O)C(O)O	2-chloropyridin-5-yl-methyl
241	OC(O)C(O)O	2-furanyl
242	OC(O)C(O)O	2-pyrimidinyl
243	OC(O)C(O)O	2-oxazolyl
244	OC(O)C(O)O	5-[1,2,4]-oxadiazolyl
245	OC(O)C(O)O	tetrazolyl
246	S(O) 2 NR′	H	H
247	S(O) 2 NR′	Me	H
248	S(O) 2 NR′	Et	H
249	S(O) 2 NR′	n-Pr	H
250	S(O) 2 NR′	i-Pr	H
251	S(O) 2 NR′	n-Bu	H
252	S(O) 2 NR′	i-Bu	H
253	S(O) 2 NR′	allyl	H
254	S(O) 2 NR′	CH 2 C≡CH	H
255	S(O) 2 NR′	CH═CH 2	H
256	S(O) 2 NR′	CH 2 CH 2 F	H
257	S(O) 2 NR′	CF 3	H
258	S(O) 2 NR′	CH 2 CF 3	H
259	S(O) 2 NR′	CH 2 CN	H
260	S(O) 2 NR′	cyclopropyl	H
261	S(O) 2 NR′	cyclopropylmethyl	H
262	S(O) 2 NR′	CH 2 CO 2 Me	H
263	S(O) 2 NR′	CH 2 CH 2 NMe 2	H
264	S(O) 2 NR′	CH 2 -(N-morpholinyl)	H
265	S(O) 2 NR′	2-chloropyridin-5-yl-methyl	H
266	S(O) 2 NR′	2-furanyl	H
267	S(O) 2 NR′	2-pyrimidinyl	H
268	S(O) 2 NR′	2-oxazolyl	H
269	S(O) 2 NR′	5-[1,2,4]-oxadiazolyl	H
270	S(O) 2 NR′	tetrazolyl	H
271	S(O) 2 NR′	H	Me
272	S(O) 2 NR′	Me	Me
273	S(O) 2 NR′	Et	Me
274	S(O) 2 NR′	n-Pr	Me
275	S(O) 2 NR′	i-Pr	Me
276	S(O) 2 NR′	n-Bu	Me
277	S(O) 2 NR′	i-Bu	Me
278	S(O) 2 NR′	allyl	Me
279	S(O) 2 NR′	CH 2 C≡CH	Me
280	S(O) 2 NR′	CH═CH 2	Me
281	S(O) 2 NR′	CH 2 CH 2 F	Me
282	S(O) 2 NR′	CF 3	Me
283	S(O) 2 NR′	CH 2 CF 3	Me
284	S(O) 2 NR′	CH 2 CN	Me
285	S(O) 2 NR′	cyclopropyl	Me
286	S(O) 2 NR′	cyclopropylmethyl	Me
287	S(O) 2 NR′	CH 2 CO 2 Me	Me
288	S(O) 2 NR′	CH 2 CH 2 NMe 2	Me
289	S(O) 2 NR′	CH 2 -(N-morpholinyl)	Me
289	S(O) 2 NR′	2-chloropyridin-5-yl-methyl	Me
290	S(O) 2 NR′	2-furanyl	Me
291	S(O) 2 NR′	2-pyrimidinyl	Me
292	S(O) 2 NR′	2-oxazolyl	Me
293	S(O) 2 NR′	5-[1,2,4]-oxadiazolyl	Me
294	S(O) 2 NR′	tetrazolyl	Me
295	S(O) 2 NR′	H	Et
296	S(O) 2 NR′	Me	Et
297	S(O) 2 NR′	Et	Et
298	S(O) 2 NR′	n-Pr	Et
299	S(O) 2 NR′	i-Pr	Et
300	S(O) 2 NR′	n-Bu	Et
301	S(O) 2 NR′	i-Bu	Et
302	S(O) 2 NR′	allyl	Et
303	S(O) 2 NR′	CH 2 C≡CH	Et
304	S(O) 2 NR′	CH═CH 2	Et
305	S(O) 2 NR′	CH 2 CH 2 F	Et
306	S(O) 2 NR′	CF 3	Et
307	S(O) 2 NR′	CH 2 CF 3	Et
308	S(O) 2 NR′	CH 2 CN	Et
309	S(O) 2 NR′	cyclopropyl	Et
310	S(O) 2 NR′	cyclopropylmethyl	Et
311	S(O) 2 NR′	CH 2 CO 2 Me	Et
312	S(O) 2 NR′	CH 2 CH 2 NMe 2	Et
313	S(O) 2 NR′	CH 2 -(N-morpholinyl)	Et
314	S(O) 2 NR′	2-chloropyridin-5-yl-methyl	Et
315	S(O) 2 NR′	2-furanyl	Et
316	S(O) 2 NR′	2-pyrimidinyl	Et
317	S(O) 2 NR′	2-oxazolyl	Et
318	S(O) 2 NR′	5-[1,2,4]-oxadiazolyl	Et
319	S(O) 2 NR′	tetrazolyl	Et

TABLE 2
Ex.				m.p.
No.	Y	R	R′	[° C.]
1	O	H		128
2	O	Et		oil
3	O	n-Pr
4	O	i-Pr		oil
5	O	n-Bu		oil
6	O	i-Bu		oil
7	O	allyl		oil
8	O	CH 2 C≡CH		oil
9	O	CH═CH 2
10	O	CH 2 CH 2 F
11	O	CF 3
12	O	CH 2 CF 3		oil
13	O	CH 2 CN
14	O	cyclopropyl
15	O	cyclopropylmethyl		oil
16	O	CH 2 CO 2 Me
17	O	CH 2 CH 2 NMe 2
18	O	CH 2 -(N-morpholinyl)		oil
19	O	2-chloropyridin-5-yl-methyl
20	O	2-furanyl
21	O	2-pyrimidinyl
22	O	2-oxazolyl
23	O	5-[1,2,4]-oxindazolyl
24	O	tetrazolyl
25	O	1,3-oxindol-2-yl		oil
26	O	CH 2 CH 2 OMe		oil
27	O	CH 2 CH 2 OCH 2 CH 2 OMe		oil
28	O	CH 2 CH 2 SCH 2 CH 3		oil
29	S	H
30	S	Et		oil
31	S	n-Pr		oil
32	S	i-Pr
33	S	n-Bu
34	S	i-Bu		oil
35	S	allyl		oil
36	S	CH 2 C≡CH
37	S	CH═CH 2
38	S	CH 2 CH 2 F
39	S	CF 3		oil
40	S	CH 2 CF 3		oil
41	S	CH 2 CN
42	S	cyclopropyl
43	S	cyclopropylmethyl
44	S	CH 2 CO 2 Me		oil
45	S	CH 2 CO 2 Et		oil
46	S	CH 2 CH 2 CO 2 Me		oil
47	S	CH 2 CH 2 NMe 2
48	S	CH 2 -(N-morpholinyl)
49	S	2-chloropyridin-5-yl-methyl
50	S	2-furanyl
51	S	2-pyridinyl		oil
52	S	2-pyrimidinyl		crystal-
				line
53	S	2-oxazolyl
54	S	5-[1,2,4]-oxadiazolyl
55	S	tetrazolyl
56	S	CH 2 CH 2 OH		oil
57	S	Ac		oil
58	S
59	NR′(CO)			136
60	NR′C(O)O	CMe 3	H	Öl
61	NR′		CO 2 allyl	Öl
62	NR′SO 2	C(H)Cl 2	Me	Öl
63	NR′SO 2	Bu	Me	Öl
64	NR′SO 2	Pr	Me	Öl
65	S	N-Me-imidazol-2-yl		solid
66	S	[1,2,4]-triazol-3-yl		solid
67	S	4-Me-[1,2,4]-triazol-3-yl		crystal-
				line
68	S	4-Me-tetrazol-5-yl		solid
69	S	2-thiazolin-2-yl		crystal-
				line
70	S	cyclohexyl		wax
71	S(O)	Et
72	S(O)	n-Pr
73	S(O)	i-Pr		oil
74	S(O)	n-Bu
75	S(O)	i-Bu
76	S(O)	allyl
77	S(O)	CH 2 C≡CH
78	S(O)	CH═CH 2
79	S(O)	CH 2 CH 2 F
80	S(O)	CF 3		solid
		CH 2 CF 3
81	S(O)	CH 2 CN		129
82	S(O)	cyclopropyl
83	S(O)	cyclopropylmethyl
84	S(O)	CH 2 CO 2 Me
85	S(O)	CH 2 CH 2 NMe 2
86	S(O)	CH 2 -(N-morpholinyl)
87	S(O)	2-chloropyridin-5-yl-methyl
88	S(O)	2-furanyl
89	S(O)	2-pyrimidinyl
90	S(O)	2-oxazolyl
91	S(O)	5-[1,2,4]-oxadiazolyl
92	S(O)	tetrazolyl
93	S(O)
94	S(O) 2	Me		92
95	S(O) 2	Et
96	S(O) 2	n-Pr		73
97	S(O) 2	i-Pr		109
98	S(O) 2	n-Bu
99	S(O) 2	n-Hex		87
100	S(O) 2	i-Bu
101	S(O) 2	allyl
102	S(O) 2	CH 2 C≡CH
103	S(O) 2	CH═CH 2
104	S(O) 2	CH 2 CH 2 F
105	S(O) 2	CF 3
106	S(O) 2	CH 2 CF 3		crystal-
				line
107	S(O) 2	CH 2 CN
108	S(O) 2	cyclopropyl
109	S(O) 2	cyclopropylmethyl
110	S(O) 2	CH 2 CO 2 Me
111	S(O) 2	CH 2 CH 2 NMe 2
112	S(O) 2	CH 2 -(N-morpholinyl)
113	S(O) 2	2-chloropyridin-5-yl-methyl
114	S(O) 2	2-furanyl
115	S(O) 2	2-furfuryl		99
116	S(O) 2	2-thienyl		100
117	S(O) 2	2-pyrimidinyl
118	S(O) 2	2-oxazolyl
119	S(O) 2	5-[1,2,4]-oxadiazolyl
120	S(O) 2	tetrazolyl
121	S(O) 2	ONa		214
122	S(O) 2	p-F-benzyl		156
123	OC(O)	H
124	OC(O)	Me
125	OC(O)	Et		oil
126	OC(O)	n-Pr
127	OC(O)	i-Pr
128	OC(O)	n-Bu
129	OC(O)	i-Bu		oil
130	OC(O)	t-Bu		oil
131	OC(O)	allyl
132	OC(O)	CH 2 C≡CH
133	OC(O)	CH═CH 2		oil
134	OC(O)	CH 2 CH 2 F
135	OC(O)	CF 3
136	OC(O)	CH 2 CF 3
137	OC(O)	CH 2 CH 2 SiMe 3		oil
138	OC(O)	CH 2 CN		oil
139	OC(O)	cyclopropyl
140	OC(O)	cyclopropylmethyl
141	OC(O)	CH 2 CO 2 Me		oil
142	OC(O)	CH 2 CH 2 NMe 2
143	OC(O)	CH 2 OMe
144	OC(O)	CH 2 -(N-morpholinyl)
145	OC(O)	2-chloropyridin-5-yl-methyl
146	OC(O)	2-furanyl
147	OC(O)	2-pyrimidinyl
148	OC(O)	2-oxazolyl
149	OC(O)	5-[1,2,4]-oxadiazolyl
150	OC(O)	tetrazolyl
151	OC(O)	2-oxopyrrolidin-5-yl		oil
152	OC(O)O	H
153	OC(O)O	Me		oil
154	OC(O)O	Et		oil
155	OC(O)O	n-Pr		oil
156	OC(O)O	i-Pr
157	OC(O)O	n-Bu
158	OC(O)O	i-Bu
159	OC(O)O	allyl
160	OC(O)O	CH 2 C≡CH
161	OC(O)O	CH═CH 2
162	OC(O)O	CH 2 CH 2 F
163	OC(O)O	CF 3
164	OC(O)O	CH 2 CF 3
165	OC(O)O	CH 2 CN
166	OC(O)O	cyclopropyl
167	OC(O)O	cyclopropylmethyl
168	OC(O)O	CH 2 CO 2 Me
169	OC(O)O	CH 2 CH 2 NMe 2
170	OC(O)O	CH 2 -(N-morpholinyl)
171	OC(O)O	2-chloropyridin-5-yl-methyl
172	OC(O)O	2-furanyl
173	OC(O)O	2-pyrimidinyl
174	OC(O)O	2-oxazolyl
175	OC(O)O	5-[1,2,4]-oxadiazolyl
176	OC(O)O	tetrazolyl
177	OC(O)NR′	H	H
178	OC(O)NR′	Me	H
179	OC(O)NR′	Et	H
180	OC(O)NR′	n-Pr	H
181	OC(O)NR′	i-Pr	H
182	OC(O)NR′	n-Bu	H
183	OC(O)NR′	i-Bu	H
184	OC(O)NR′	allyl	H
185	OC(O)NR′	CH 2 C≡CH	H
186	OC(O)NR′	CH═CH 2	H
187	OC(O)NR′	CH 2 CH 2 F	H
188	OC(O)NR′	CF 3	H
189	OC(O)NR′	CH 2 CF 3	H
190	OC(O)NR′	CH 2 CN	H
191	OC(O)NR′	cyclopropyl	H
192	OC(O)NR′	cyclopropylmethyl	H
193	OC(O)NR′	CH 2 CO 2 Me	H
194	OC(O)NR′	CH 2 CH 2 NMe 2	H
195	OC(O)NR′	CH 2 -(N-morpholinyl)	H
196	OC(O)NR′	2-chloropyridin-5-yl-methyl	H
197	OC(O)NR′	2-furanyl	H
198	OC(O)NR′	2-pyrimidinyl	H
199	OC(O)NR′	2-oxazolyl	H
200	OC(O)NR′	5-[1,2,4]-oxadiazolyl	H
201	OC(O)NR′	tetrazolyl	H
202	OC(O)NR′	H	Me
203	OC(O)NR′	Me	Me	oil
204	OC(O)NR′	Et	Me
205	OC(O)NR′	n-Pr	Me
206	OC(O)NR′	i-Pr	Me
207	OC(O)NR′	n-Bu	Me
208	OC(O)NR′	i-Bu	Me
209	OC(O)NR′	allyl	Me
210	OC(O)NR′	CH 2 C≡CH	Me
211	OC(O)NR′	CH═CH 2	Me
212	OC(O)NR′	CH 2 CH 2 F	Me
213	OC(O)NR′	CF 3	Me
214	OC(O)NR′	CH 2 CF 3	Me
215	OC(O)NR′	CH 2 CN	Me
216	OC(O)NR′	cyclopropyl	Me
217	OC(O)NR′	cyclopropylmethyl	Me
218	OC(O)NR′	CH 2 CO 2 Me	Me
219	OC(O)NR′	CH 2 CH 2 NMe 2	Me
220	OC(O)NR′	CH 2 -(N-morpholinyl)	Me
221	OC(O)NR′	2-chloropyridin-5-yl-methyl	Me
222	OC(O)NR′	2-furanyl	Me
223	OC(O)NR′	2-pyrimidinyl	Me
224	OC(O)NR′	2-oxazolyl	Me
225	OC(O)NR′	5-[1,2,4]-oxadiazolyl	Me
226	OC(O)NR′	tetrazolyl	Me
227	OC(O)NR′	n-Hex	Me
228	OC(O)NR′	H	Et
229	OC(O)NR′	Me	Et
230	OC(O)NR′	Et	Et
231	OC(O)NR′	n-Pr	Et
232	OC(O)NR′	i-Pr	Et
233	OC(O)NR′	n-Bu	Et
234	OC(O)NR′	i-Bu	Et
235	OC(O)NR′	allyl	Et
236	OC(O)NR′	CH 2 C≡CH	Et
237	OC(O)NR′	CH═CH 2	Et
238	OC(O)NR′	CH 2 CH 2 F	Et
239	OC(O)NR′	CF 3	Et
240	OC(O)NR′	CH 2 CF 3	Et
241	OC(O)NR′	CH 2 CN	Et
242	OC(O)NR′	cyclopropyl	Et
243	OC(O)NR′	cyclopropylmethyl	Et
244	OC(O)NR′	CH 2 CO 2 Me	Et
245	OC(O)NR′	CH 2 CH 2 NMe 2	Et
246	OC(O)NR′	CH 2 -(N-morpholinyl)	Et
247	OC(O)NR′	2-chloropyridin-5-yl-methyl	Et
248	OC(O)NR′	2-furanyl	Et
249	OC(O)NR′	2-pyrimidinyl	Et
250	OC(O)NR′	2-oxazolyl	Et
251	OC(O)NR′	5-[1,2,4]-oxadiazolyl	Et
252	OC(O)NR′	tetrazolyl	Et
253	OC(O)NR′	H	Et
254	OC(O)C(O)O	H
255	OC(O)C(O)O	Me		oil
256	OC(O)C(O)O	Et		oil
257	OC(O)C(O)O	n-Pr
258	OC(O)C(O)O	i-Pr
259	OC(O)C(O)O	n-Bu
260	OC(O)C(O)O	i-Bu
261	OC(O)C(O)O	allyl
262	OC(O)C(O)O	CH 2 C≡CH
263	OC(O)C(O)O	CH═CH 2
264	OC(O)C(O)O	CH 2 CH 2 F
265	OC(O)C(O)O	CF 3
266	OC(O)C(O)O	CH 2 CF 3
267	OC(O)C(O)O	CH 2 CN
268	OC(O)C(O)O	cyclopropyl
269	OC(O)C(O)O	cyclopropylmethyl
270	OC(O)C(O)O	CH 2 CO 2 Me
271	OC(O)C(O)O	CH 2 CH 2 NMe 2
272	OC(O)C(O)O	CH 2 -(N-morpholinyl)
273	OC(O)C(O)O	2-chloropyridin-5-yl-methyl
274	OC(O)C(O)O	2-furanyl
275	OC(O)C(O)O	2-pyrimidinyl
276	OC(O)C(O)O	2-oxazolyl
277	OC(O)C(O)O	5-[1,2,4]-oxadiazolyl
278	OC(O)C(O)O	tetrazolyl
279	S(O) 2 NR′	H	H
280	S(O) 2 NR′	Me	H
281	S(O) 2 NR′	Et	H
282	S(O) 2 NR′	n-Pr	H
283	S(O) 2 NR′	i-Pr	H	93
284	S(O) 2 NR′	n-Bu	H
285	S(O) 2 NR′	i-Bu	H
286	S(O) 2 NR′	allyl	H	83
287	S(O) 2 NR′	CH 2 C≡CH	H
288	S(O) 2 NR′	CH═CH 2	H
289	S(O) 2 NR′	CH 2 CH 2 F	H
290	S(O) 2 NR′	CF 3	H
291	S(O) 2 NR′	CH 2 CF 3	H
292	S(O) 2 NR′	CH 2 CN	H
293	S(O) 2 NR′	cyclopropyl	H
294	S(O) 2 NR′	cyclopropylmethyl	H	solid
295	S(O) 2 NR′	CH 2 CO 2 Me	H
296	S(O) 2 NR′	CH 2 CH 2 NMe 2	H
297	S(O) 2 NR′	CH 2 -(N-morpholinyl)	H
298	S(O) 2 NR′	2-chloropyridin-5-yl-methyl	H
299	S(O) 2 NR′	2-furanyl	H
300	S(O) 2 NR′	2-pyrimidinyl	H
301	S(O) 2 NR′	2-oxazolyl	H
302	S(O) 2 NR′	5-[1,2,4]-oxadiazolyl	H
303	S(O) 2 NR′	tetrazolyl	H
304	S(O) 2 NR′	H	Me
305	S(O) 2 NR′	Me	Me
306	S(O) 2 NR′	Et	Me	oil
307	S(O) 2 NR′	n-Pr	Me
308	S(O) 2 NR′	i-Pr	Me	oil
309	S(O) 2 NR′	n-Bu	Me
310	S(O) 2 NR′	i-Bu	Me
311	S(O) 2 NR′	allyl	Me
312	S(O) 2 NR′	CH 2 C≡CH	Me	94
313	S(O) 2 NR′	CH═CH 2	Me
314	S(O) 2 NR′	CH 2 CH 2 F	Me
315	S(O) 2 NR′	CF 3	Me
316	S(O) 2 NR′	CH 2 CF 3	Me
317	S(O) 2 NR′	CH 2 CN	Me
318	S(O) 2 NR′	cyclopropyl	Me
319	S(O) 2 NR′	cyclopropylmethyl	Me
320	S(O) 2 NR′	CH 2 CO 2 Me	Me
321	S(O) 2 NR′	CH 2 CH 2 NMe 2	Me
322	S(O) 2 NR′	CH 2 -(N-morpholinyl)	Me
323	S(O) 2 NR′	2-chloropyridin-5-yl-methyl	Me
324	S(O) 2 NR′	furanyl	Me
325	S(O) 2 NR′	2-pyrimidinyl	Me
326	S(O) 2 NR′	2-oxazolyl	Me
327	S(O) 2 NR′	5-[1,2,4]-oxadiazolyl	Me
328	S(O) 2 NR′	tetrazolyl	Me
329	S(O) 2 NR′	H	Et
330	S(O) 2 NR′	Me	Et
331	S(O) 2 NR′	Et	Et
332	S(O) 2 NR′	n-Pr	Et
333	S(O) 2 NR′	i-Pr	Et	70
334	S(O) 2 NR′	n-Bu	Et
335	S(O) 2 NR′	i-Bu	Et
336	S(O) 2 NR′	allyl	Et	oil
337	S(O) 2 NR′	CH 2 C≡CH	Et
338	S(O) 2 NR′	CH═CH 2	Et
339	S(O) 2 NR′	CH 2 CH 2 F	Et
340	S(O) 2 NR′	CF 3	Et
341	S(O) 2 NR′	CH 2 CF 3	Et
342	S(O) 2 NR′	CH 2 CN	Et
343	S(O) 2 NR′	cyclopropyl	Et
344	S(O) 2 NR′	cyclopropylmethyl	Et
345	S(O) 2 NR′	CH 2 CO 2 Me	Et
346	S(O) 2 NR′	CH 2 CH 2 NMe 2	Et
347	S(O) 2 NR′	CH 2 -(N-morpholinyl)	Et
348	S(O) 2 NR′	2-chloropyridin-5-yl-methyl	Et
349	S(O) 2 NR′	furanyl	Et
350	S(O) 2 NR′	2-pyrimidinyl	Et
351	S(O) 2 NR′	2-oxazolyl	Et
352	S(O) 2 NR′	5-[1,2,4]-oxadiazolyl	Et
353	S(O) 2 NR′	tetrazolyl	Et
354	S(O) 2 NR′	n-Pr	n-Pr	oil
355	S(O) 2 NR′	CH 2 SCH 2 CH 2	n-Pr
356	S(O) 2 NR′	CH 2 CH 2 CH 2 CH 2 CH 2	n-Pr	152
357	S(O) 2 NR′	CH 2 CH═CHCH 2 CH 2	n-Pr	138
358	S	2-methylmercapto-1,3,4-thiadiazol-5-yl	92
359	S	5-(trifluoromethyl)-pyridin-2-yl	78
360	S	3-(trifluoromethyl)-pyridin-2-yl	68
361	S	4-methylthiazol-2-yl	oil
362	S	3-(methylmercapto)-1,2,4-thiadiazol-	oil
		5-yl
363	S	4-pyridinyl	88
364	S	2-methylfuran-3-yl	oil
365	S	4-(trifluoromethoxy)-phenyl	57
366	S	2-imidazolyl	171
367	S	5-methyl-1,2,4-triazol-3-yl	95
368	S	2-thiazolyl	oil
369	S	dimethylaminothiocarbonyl	solid
370	S	4,6-dimethylpyrimidin-2-yl	oil
371	S	5-methyl-1,3,4-thiadiazol-2-yl	98
372	NR′C(S)NH	CO 2 Et	H	136
373	NR′C(O)	CH(imidazolyl-)CF 2 C(O)	oil
374	NR′C(O)	CH(Me)CH 2 C(O)	oil
375	NR′C(O)	CMe 2 CH 2 C(O)	oil
376	NR′C(O)	CH(Me)CH(Me)C(O)	oil
377	NR′C(O)	CH 2 CH 2 CH 2 C(O)	oil
378	NR′C(O)	CH(Me)CH 2 CH 2 C(O)	oil
379	NR′C(O)	CH 2 CH(Me)CH 2 C(O)	oil
380	NR′C(O)	CH 2 CMe 2 CH 2 C(O)	oil
381	NR′C(O)	CH 2 C [—(CH 2 ) 4 —]CH 2 C(O)	oil
382	NR′C(O)		192
383	NR′C(O)N(H)	CH(CHMe 2 )CO 2 Et	H	oil
384	NR′C(S)N(H)	Et	H	oil
385	NR′C(S)N(H)	CMe 3	H	113
386	NR′C(S)N(H)	-p-Tol	H	oil
387	NR′C(O)		H	148
388	NR′C(O)N(H)	Et	H	144
389	NR′C(O)N(H)	C(H)Me 2	H	159
390	NR′C(O)N(H)	Bu	H	117
391	NR′C(O)N(H)	(CH 2 ) 4 Me	H	118
392	NR′C(O)N(H)	cyclohexyl	H	160
393	NR′C(O)N(H)	C(H)MeCO 2 Et	H	157
394	NR′C(O)N(H)	C(O)Ph	H	182
395	NR′C(O)N(H)	(4-CF 3 -Ph)	H	170
396	NR′C(O)N(H)	(2,6-C 6 H 3 F 2 )	H	193
397	NR′C(O)		oil
398	NR′C(O)	CH 2 C(H)PhCH 2 C(O)	oil
399	NR′C(O)	CMe═CMeC(O)	oil
400	NR′C(O)		oil
401	NR′(CO)N(H)	CMe 3	H	120
402	NR′C(O)O	CH 2 C≡CH	H	solid
403	NR′SO 2	C(H)Me 2	H	oil
404	NR′C(O)	CH 2 OC(O)Me	H	80
405	NR′C(O)	(CH 2 ) 3 Cl	H	56
406	NR′C(O)	(CH 2 ) 2 SMe	H	96
407	NR′C(O)O	Bu	H	oil
408	NR′C(O)O	cyclopentyl	H	oil
409	NR′C(O)	CH 2 CH 2 C(O)		87
410	NR′C(O)N(H)	Ph	H	129
411	NR′H + HSO 4 −	H	H	solid

TABLE 3
Ex.				m.p.
No.	Y	R	R′	[° C.]
1	O	n-Pr		oil
2	O	i-Pr		oil
3	O	n-Bu
4	O	i-Bu
5	O	allyl		oil
6	O	CH 2 C≡CH		oil
7	O	CH═CH 2
8	O	CH 2 CH 2 F
9	O	CF 3
10	O	CH 2 CF 3
11	O	CH 2 CN
12	O	cyclopropyl
13	O	cyclopropylmethyl
14	O	CH 2 CO 2 Me
15	O	CH 2 CH 2 NMe 2
16	O	CH 2 -(N-morpholinyl)
17	O	2-chloropyridin-5-yl-methyl
18	O	n-Hex
19	O	2-furanyl
20	O	2-pyrimidinyl
21	O	2-oxazolyl
22	O	5-[1,2,4]-oxadiazolyl
23	O	tetrazolyl
24	O	2-hexahydropropanyl
25	S	H
26	S	Et
27	S	i-Pr		oil
28	S	n-Bu
29	S	i-Bu
30	S	allyl
31	S	CH 2 C≡CH
32	S	CH═CH 2
33	S	CH 2 CH 2 F
34	S	CF 3
35	S	CH 2 CF 3		oil
36	S	CH 2 CN
37	S	cyclopropyl
38	S	cyclopropylmethyl
39	S	CH 2 CO 2 Me
40	S	CH 2 CH 2 NMe 2
41	S	CH 2 -(N-morpholinyl)
42	S	2-chloropyridin-5-yl-methyl
43	S	n-Hex
44	S	2-furanyl
45	S	2-pyrimidinyl
46	S	2-oxazolyl
47	S	5-[1,2,4]-oxadiazolyl
48		tetrazolyl
49	S			oil
50	S(O)	Me
51	S(O)	Et
52	S(O)	n-Pr
53	S(O)	i-Pr
54	S(O)	n-Bu
55	S(O)	i-Bu
56	S(O)	allyl
57	S(O)	CH 2 C≡CH
58	S(O)	CH═CH 2
59	S(O)	CH 2 CH 2 F
60	S(O)	CF 3
61	S(O)	CH 2 CF 3
62	S(O)	CH 2 CN
63	S(O)	cyclopropyl
64	S(O)	cyclopropylmethyl
65	S(O)	CH 2 CO 2 Me
66	S(O)	CH 2 CH 2 NMe 2
67	S(O)	CH 2 -(N-morpholinyl)
68	S(O)	2-chloropyridin-5-yl-methyl
69	S(O)	n-Hex
70	S(O)	2-furanyl
71	S(O)	2-pyrimidinyl
72	S(O)	2-oxazolyl
73	S(O)	5-[1,2,4]-oxadiazolyl
74	S(O)	tetrazolyl
75	S(O) 2	Me		84
76	S(O) 2	Et
77	S(O) 2	n-Pr
78	S(O) 2	i-Pr
79	S(O) 2	n-Bu
80	S(O) 2	i-Bu
81	S(O) 2	allyl
82	S(O) 2	CH 2 C≡CH
83	S(O) 2	CH═CH 2
84	S(O) 2	CH 2 CH 2 F
85	S(O) 2	CF 3
86	S(O) 2	CH 2 CF 3
87	S(O) 2	CH 2 CN
88	S(O) 2	cyclopropyl
89	S(O) 2	cyclopropylmethyl
90	S(O) 2	CH 2 CO 2 Me
91	S(O) 2	CH 2 CH 2 NMe 2
92	S(O) 2	CH 2 -(N-morpholinyl)
93	S(O) 2	2-chloropyridin-5-yl-methyl
94	S(O) 2	n-Hex
95	S(O) 2	furanyl
96	S(O) 2	2-pyrimidinyl
97	S(O) 2	2-oxazolyl
98	S(O) 2	5-[1,2,4]-oxadiazolyl
99	S(O) 2	tetrazolyl
100	OC(O)	H
101	OC(O)	Et
102	OC(O)	n-Pr
103	OC(O)	i-Pr
104	OC(O)	n-Bu
105	OC(O)	i-Bu
106	OC(O)	allyl
107	OC(O)	CH 2 C≡CH
108	OC(O)	CH═CH 2
109	OC(O)	CH 2 CH 2 F
110	OC(O)	CF 3
111	OC(O)	CH 2 CF 3
112	OC(O)	CH 2 CN
113	OC(O)	cyclopropyl
114	OC(O)	cyclopropylmethyl
115	OC(O)	CH 2 CO 2 Me
116	OC(O)	CH 2 CH 2 NMe 2
117	OC(O)	CH 2 -(N-morpholinyl)
118	OC(O)	2-chloropyridin-5-yl-methyl
119	OC(O)	n-Hex
120	OC(O)	2-furanyl
121	OC(O)	2-pyrimidinyl
122	OC(O)	2-oxazolyl
123	OC(O)	5-[1,2,4]-oxadiazolyl
124	OC(O)	tetrazolyl
125	OC(O)O	Me
126	OC(O)O	Et
127	OC(O)O	n-Pr
128	OC(O)O	i-Pr
129	OC(O)O	n-Bu
130	OC(O)O	i-Bu
131	OC(O)O	allyl
132	OC(O)O	CH 2 C≡CH
133	OC(O)O	CH═CH 2
134	OC(O)O	CH 2 CH 2 F
135	OC(O)O	CF 3
136	OC(O)O	CH 2 CF 3
137	OC(O)O	CH 2 CN
138	OC(O)O	cyclopropyl
139	OC(O)O	cyclopropylmethyl
140	OC(O)O	CH 2 CO 2 Me
141	OC(O)O	CH 2 CH 2 NMe 2
142	OC(O)O	CH 2 -(N-morpholinyl)
143	OC(O)O	2-chloropyridin-5-yl-methyl
144	OC(O)O	n-Hex
145	OC(O)O	2-furanyl
146	OC(O)O	2-pyrimidinyl
147	OC(O)O	2-oxazolyl
148	OC(O)O	5-[1,2,4]-oxadiazolyl
149	OC(O)O	tetrazolyl
150	OC(O)NR′	H	H
151	OC(O)NR′	Me	H
152	OC(O)NR′	Et	H
154	OC(O)NR′	n-Pr	H
155	OC(O)NR′	i-Pr	H
156	OC(O)NR′	n-Bu	H
157	OC(O)NR′	i-Bu	H
158	OC(O)NR′	allyl	H
159	OC(O)NR′	CH 2 C≡CH	H
160	OC(O)NR′	CH═CH 2	H
161	OC(O)NR′	CH 2 CH 2 F	H
162	OC(O)NR′	CF 3	H
163	OC(O)NR′	CH 2 CF 3	H
164	OC(O)NR′	CH 2 CN	H
165	OC(O)NR′	cyclopropyl	H
166	OC(O)NR′	cyclopropylmethyl	H
167	OC(O)NR′	CH 2 CO 2 Me	H
168	OC(O)NR′	CH 2 CH 2 NMe 2	H
169	OC(O)NR′	CH 2 -(N-morpholinyl)	H
170	OC(O)NR′	2-chloropyridin-5-yl-methyl	H
171	OC(O)NR′	n-Hex	H
172	OC(O)NR′	2-furanyl	H
173	OC(O)NR′	2-pyrimidinyl	H
174	OC(O)NR′	2-oxazolyl	H
175	OC(O)NR′	5-[1,2,4]-oxadiazolyl	H
176	OC(O)NR′	tetrazolyl	H
177	OC(O)NR′	H	Me
178	OC(O)NR′	Me	Me
179	OC(O)NR′	Et	Me
180	OC(O)NR′	n-Pr	Me
181	OC(O)NR′	i-Pr	Me
182	OC(O)NR′	n-Bu	Me
183	OC(O)NR′	i-Bu	Me
184	OC(O)NR′	allyl	Me
185	OC(O)NR′	CH 2 C≡CH	Me
186	OC(O)NR′	CH═CH 2	Me
187	OC(O)NR′	CH 2 CH 2 F	Me
188	OC(O)NR′	CF 3	Me
189	OC(O)NR′	CH 2 CF 3	Me
190	OC(O)NR′	CH 2 CN	Me
191	OC(O)NR′	cyclopropyl	Me
192	OC(O)NR′	cyclopropylmethyl	Me
193	OC(O)NR′	CH 2 CO 2 Me	Me
194	OC(O)NR′	CH 2 CH 2 NMe 2	Me
195	OC(O)NR′	CH 2 -(N-morpholinyl)	Me
196	OC(O)NR′	2-chloropyridin-5-yl-methyl	Me
197	OC(O)NR′	n-Hex	Me
198	OC(O)NR′	2-furanyl	Me
199	OC(O)NR′	2-pyrimidinyl	Me
200	OC(O)NR′	2-oxazolyl	Me
201	OC(O)NR′	5-[1,2,4]-oxadiazolyl	Me
202	OC(O)NR′	tetrazolyl	Me
203	OC(O)NR′	H	Et
204	OC(O)NR′	Me	Et
205	OC(O)NR′	Et	Et
206	OC(O)NR′	n-Pr	Et
207	OC(O)NR′	i-Pr	Et
208	OC(O)NR′	n-Bu	Et
209	OC(O)NR′	i-Bu	Et
210	OC(O)NR′	allyl	Et
211	OC(O)NR′	CH 2 C≡CH	Et
212	OC(O)NR′	CH═CH 2	Et
213	OC(O)NR′	CH 2 CH 2 F	Et
214	OC(O)NR′	CF 3	Et
215	OC(O)NR′	CH 2 CF 3	Et
216	OC(O)NR′	CH 2 CN	Et
217	OC(O)NR′	cyclopropyl	Et
218	OC(O)NR′	cyclopropylmethyl	Et
219	OC(O)NR′	CH 2 CO 2 Me	Et
220	OC(O)NR′	CH 2 CH 2 NMe 2	Et
221	OC(O)NR′	CH 2 -(N-morpholinyl)	Et
222	OC(O)NR′	2-chloropyridin-5-yl-methyl	Et
223	OC(O)NR′	n-Hex	Et
224	OC(O)NR′	2-furanyl	Et
225	OC(O)NR′	2-pyrimidinyl	Et
226	OC(O)NR′	2-oxazolyl	Et
227	OC(O)NR′	5-[1,2,4]-oxadiazolyl	Et
228	OC(O)NR′	tetrazolyl	Et
229	OC(O)C(O)O	H
230	OC(O)C(O)O	Me
231	OC(O)C(O)O	Et
232	OC(O)C(O)O	n-Pr
233	OC(O)C(O)O	i-Pr
234	OC(O)C(O)O	n-Bu
235	OC(O)C(O)O	i-Bu
236	OC(O)C(O)O	allyl
237	OC(O)C(O)O	CH 2 C≡CH
238	OC(O)C(O)O	CH═CH 2
239	OC(O)C(O)O	CH 2 CH 2 F
240	OC(O)C(O)O	CF 3
241	OC(O)C(O)O	CH 2 CF 3
242	OC(O)C(O)O	CH 2 CN
243	OC(O)C(O)O	cyclopropyl
244	OC(O)C(O)O	cyclopropylmethyl
245	OC(O)C(O)O	CH 2 CO 2 Me
246	OC(O)C(O)O	CH 2 CH 2 NMe 2
247	OC(O)C(O)O	CH 2 -(N-morpholinyl)
248	OC(O)C(O)O	2-chloropyridin-5-yl-methyl
249	OC(O)C(O)O	n-Hex
250	OC(O)C(O)O	furanyl
251	OC(O)C(O)O	2-pyrimidinyl
252	OC(O)C(O)O	2-oxazolyl
253	OC(O)C(O)O	5-[1,2,4]-oxadiazolyl
254	OC(O)C(O)O	tetrazolyl
255	S(O) 2 NR′	H	H
256	S(O) 2 NR′	Me	H
257	S(O) 2 NR′	Et	H
258	S(O) 2 NR′	n-Pr	H
259	S(O) 2 NR′	i-Pr	H
260	S(O) 2 NR′	n-Bu	H
261	S(O) 2 NR′	i-Bu	H
262	S(O) 2 NR′	allyl	H
263	S(O) 2 NR′	CH 2 C≡CH	H
264	S(O) 2 NR′	CH═CH 2	H
265	S(O) 2 NR′	CH 2 CH 2 F	H
266	S(O) 2 NR′	CF 3	H
267	S(O) 2 NR′	CH 2 CF 3	H
268	S(O) 2 NR′	CH 2 CN	H
269	S(O) 2 NR′	cyclopropyl	H
270	S(O) 2 NR′	cyclopropylmethyl	H
271	S(O) 2 NR′	CH 2 CO 2 Me	H
272	S(O) 2 NR′	CH 2 CH 2 NMe 2	H
273	S(O) 2 NR′	CH 2 -(N-morpholinyl)	H
274	S(O) 2 NR′	2-chloropyridin-5-yl-methyl	H
275	S(O) 2 NR′	n-Hex	H
276	S(O) 2 NR′	furanyl	H
277	S(O) 2 NR′	2-pyrimidinyl	H
278	S(O) 2 NR′	2-oxazolyl	H
279	S(O) 2 NR′	5-[1,2,4]-oxadiazolyl
280	S(O) 2 NR′	tetrazolyl
281	S(O) 2 NR′	H	Me
282	S(O) 2 NR′	Me	Me
283	S(O) 2 NR′	Et	Me
284	S(O) 2 NR′	n-Pr	Me
285	S(O) 2 NR′	i-Pr	Me
286	S(O) 2 NR′	n-Bu	Me
287	S(O) 2 NR′	i-Bu	Me
288	S(O) 2 NR′	allyl	Me
289	S(O) 2 NR′	CH 2 C≡CH	Me
290	S(O) 2 NR′	CH═CH 2	Me
291	S(O) 2 NR′	CH 2 CH 2 F	Me
292	S(O) 2 NR′	CF 3	Me
293	S(O) 2 NR′	CH 2 CF 3	Me
294	S(O) 2 NR′	CH 2 CN	Me
295	S(O) 2 NR′	cyclopropyl	Me
296	S(O) 2 NR′	cyclopropylmethyl	Me
297	S(O) 2 NR′	CH 2 CO 2 Me	Me
298	S(O) 2 NR′	CH 2 CH 2 NMe 2	Me
299	S(O) 2 NR′	CH 2 -(N-morpholinyl)	Me
300	S(O) 2 NR′	2-chloropyridin-5-yl-methyl	Me
301	S(O) 2 NR′	n-Hex	Me
302	S(O) 2 NR′	furanyl	Me
303	S(O) 2 NR′	2-pyrimidinyl	Me
304	S(O) 2 NR′	2-oxazolyl	Me
305	S(O) 2 NR′	5-[1,2,4]-oxadiazolyl	Me
306	S(O) 2 NR′	tetrazolyl	Me
307	S(O) 2 NR′	H	Et
308	S(O) 2 NR′	Me	Et
309	S(O) 2 NR′	Et	Et
310	S(O) 2 NR′	n-Pr	Et
311	S(O) 2 NR′	i-Pr	Et
312	S(O) 2 NR′	n-Bu	Et
313	S(O) 2 NR′	i-Bu	Et
314	S(O) 2 NR′	allyl	Et
315	S(O) 2 NR′	CH 2 C≡CH	Et
316	S(O) 2 NR′	CH═CH 2	Et
317	S(O) 2 NR′	CH 2 CH 2 F	Et
318	S(O) 2 NR′	CF 3	Et
319	S(O) 2 NR′	CH 2 CF 3	Et
320	S(O) 2 NR′	CH 2 CN	Et
321	S(O) 2 NR′	cyclopropyl	Et
322	S(O) 2 NR′	cyclopropylmethyl	Et
323	S(O) 2 NR′	CH 2 CO 2 Me	Et
324	S(O) 2 NR′	CH 2 CH 2 NMe 2	Et
325	S(O) 2 NR′	CH 2 -(N-morpholinyl)	Et
326	S(O) 2 NR′	2-chloropyridin-5-yl-methyl	Et
327	S(O) 2 NR′	n-Hex	Et
328	S(O) 2 NR′	furanyl	Et
329	S(O) 2 NR′	n-Hex	Et
330	S(O) 2 NR′	2-pyrimidinyl	Et
331	S(O) 2 NR′	2-oxazolyl	Et
332	S(O) 2 NR′	5-[1,2,4]-oxadiazolyl	Et
333	S(O) 2 NR′	tetrazolyl	Et

TABLE 4
Ex.				m.p.
No.	Y	R	R′	[° C.]
1	O	H
2	O	Me
3	O	Et		oil
4	O	n-Pr
5	O	i-Pr
6	O	n-Bu
7	O	i-Bu
8	O	allyl
9	O	CH 2 C≡CH
10	O	CH═CH 2
11	O	CH 2 CH 2 F
12	O	CF 3
13	O	CH 2 CF 3
14	O	CH 2 CN
15	O	cyclopropyl
16	O	cyclopropylmethyl
17	O	CH 2 CO 2 Me
18	O	CH 2 CH 2 NMe 2
19	O	CH 2 -(N-morpholinyl)
20	O	2-chloropyridin-5-yl-methyl
21	O	n-Hex
22	O	2-furanyl
23	O	2-pyrimidinyl
24	O	2-oxazolyl
25	O	5-[1,2,4]-oxadiazolyl
26	O	tetrazolyl
27	S	H
28	S	Me
29	S	Et
30	S	n-Pr
31	S	i-Pr
32	S	n-Bu
33	S	i-Bu
34	S	allyl
35	S	CH 2 C≡CH
36	S	CH═CH 2
37	S	CH 2 CH 2 F
38	S	CF 3
39	S	CH 2 CF 3
40	S	CH 2 CN
41	S	cyclopropyl
42	S	cyclopropylmethyl
43	S	CH 2 CO 2 Me
44	S	CH 2 CH 2 NMe 2
45	S	CH 2 -(N-morpholinyl)
46	S	2-chloropyridin-5-yl-methyl
47	S	n-Hex
48	S	2-furanyl
49	S	2-pyrimidinyl
50	S	2-oxazolyl
51	S	5-[1,2,4]-oxadiazolyl
52	S	tetrazolyl
53	S(O)	H
54	S(O)	Me
55	S(O)	Et
56	S(O)	n-Pr
57	S(O)	i-Pr
58	S(O)	n-Bu
59	S(O)	i-Bu
60	S(O)	allyl
61	S(O)	CH 2 C═CH
62	S(O)	CH═CH 2
63	S(O)	CH 2 CH 2 F
64	S(O)	CF 3
65	S(O)	CH 2 CF 3
66	S(O)	CH 2 CN
67	S(O)	cyclopropyl
68	S(O)	cyclopropylmethyl
69	S(O)	CH 2 CO 2 Me
70	S(O)	CH 2 CH 2 NMe 2
71	S(O)	CH 2 -(N-morpholinyl)
72	S(O)	2-chloropyridin-5-yl-methyl
73	S(O)	n-Hex
74	S(O)	2-furanyl
75	S(O)	2-pyrimidinyl
76	S(O)	2-oxazolyl
77	S(O)	5-[1,2,4]-oxadiazolyl
78	S(O)	tetrazolyl
79	S(O) 2	n-Hex
80	S(O) 2	Me
81	S(O) 2	Et
82	S(O) 2	n-Pr
83	S(O) 2	i-Pr
84	S(O) 2	n-Bu
85	S(O) 2	i-Bu
86	S(O) 2	allyl
87	S(O) 2	CH 2 C≡CH
88	S(O) 2	CH═CH 2
89	S(O) 2	CH 2 CH 2 F
90	S(O) 2	CF 3
91	S(O) 2	CH 2 CF 3
92	S(O) 2	CH 2 CN
93	S(O) 2	cyclopropyl
94	S(O) 2	cyclopropylmethyl
95	S(O) 2	CH 2 CO 2 Me
96	S(O) 2	CH 2 CH 2 NMe 2
97	S(O) 2	CH 2 -(N-morpholinyl)
98	S(O) 2	2-chloropyridin-5-yl-methyl
99	S(O) 2	n-Hex
100	S(O) 2	2-furanyl
101	S(O) 2	2-pyrimidinyl
102	S(O) 2	2-oxazolyl
103	S(O) 2	5-[1,2,4]-oxadiazolyl
104		tetrazolyl
105	OC(O)	H
106	OC(O)	Me
107	OC(O)	Et
108	OC(O)	n-Pr
109	OC(O)	i-Pr
110	OC(O)	n-Bu
111	OC(O)	i-Bu
112	OC(O)	allyl
113	OC(O)	CH 2 C≡CH
114	OC(O)	CH═CH 2
115	OC(O)	CH 2 CH 2 F
116	OC(O)	CF 3
117	OC(O)	CH 2 CF 3
118	OC(O)	CH 2 CN
119	OC(O)	cyclopropyl
120	OC(O)	cyclopropylmethyl
121	OC(O)	CH 2 CO 2 Me
122	OC(O)	CH 2 CH 2 NMe 2
123	OC(O)	CH 2 -(N-morpholinyl)
124	OC(O)	2-chloropyridin-5-yl-methyl
125	OC(O)	n-Hex
126	OC(O)	2-furanyl
127	OC(O)	2-pyrimidinyl
128	OC(O)	2-oxazolyl
129	OC(O)	5-[1,2,4]-oxadiazolyl
130	OC(O)	tetrazolyl
131	OC(O)O	n-Hex
132	OC(O)O	Me
133	OC(O)O	Et
134	OC(O)O	n-Pr
135	OC(O)O	i-Pr
136	OC(O)O	n-Bu
137	OC(O)O	i-Bu
138	OC(O)O	allyl
139	OC(O)O	CH 2 C≡CH
140	OC(O)O	CH═CH 2
141	OC(O)O	CH 2 CH 2 F
142	OC(O)O	CF 3
143	OC(O)O	CH 2 CF 3
144	OC(O)O	CH 2 CN
145	OC(O)O	cyclopropyl
146	OC(O)O	cyclopropylmethyl
147	OC(O)O	CH 2 CO 2 Me
148	OC(O)O	CH 2 CH 2 NMe 2
149	OC(O)O	CH 2 -(N-morpholinyl)
150	OC(O)O	2-chloropyridin-5-yl-methyl
151	OC(O)O	n-Hex
152	OC(O)O	2-furanyl
153	OC(O)O	2-pyrimidinyl
154	OC(O)O	2-oxazolyl
155	OC(O)O	5-[1,2,4]-oxadiazolyl
156	OC(O)O	tetrazolyl
157	OC(O)NR′	H	H
158	OC(O)NR′	Me	H
159	OC(O)NR′	Et	H
160	OC(O)NR′	n-Pr	H
161	OC(O)NR′	i-Pr	H
162	OC(O)NR′	n-Bu	H
163	OC(O)NR′	i-Bu	H
164	OC(O)NR′	allyl	H
165	OC(O)NR′	CH 2 C≡CH	H
166	OC(O)NR′	CH═CH 2	H
167	OC(O)NR′	CH 2 CH 2 F	H
168	OC(O)NR′	CF 3	H
169	OC(O)NR′	CH 2 CF 3	H
170	OC(O)NR′	CH 2 CN	H
171	OC(O)NR′	cyclopropyl	H
172	OC(O)NR′	cyclopropylmethyl	H
173	OC(O)NR′	CH 2 CO 2 Me	H
174	OC(O)NR′	CH 2 CH 2 NMe 2	H
175	OC(O)NR′	CH 2 -(N-morpholinyl)	H
176	OC(O)NR′	2-chloropyridin-5-yl-methyl	H
177	OC(O)NR′	n-Hex	H
178	OC(O)NR′	2-furanyl	H
179	OC(O)NR′	2-pyrimidinyl	H
180	OC(O)NR′	2-oxazolyl	H
181	OC(O)NR′	5-[1,2,4]-oxadiazolyl	H
182	OC(O)NR′	tetrazolyl	H
183	OC(O)NR′	H	Me
184	OC(O)NR′	Me	Me
185	OC(O)NR′	Et	Me
186	OC(O)NR′	n-Pr	Me
187	OC(O)NR′	i-Pr	Me
188	OC(O)NR′	n-Bu	Me
189	OC(O)NR′	i-Bu	Me
190	OC(O)NR′	allyl	Me
191	OC(O)NR′	CH 2 C≡CH
192	OC(O)NR′	CH═CH 2	Me
193	OC(O)NR′	CH 2 CH 2 F	Me
194	OC(O)NR′	CF 3	Me
195	OC(O)NR′	CH 2 CF 3	Me
196	OC(O)NR′	CH 2 CN	Me
197	OC(O)NR′	cyclopropyl	Me
198	OC(O)NR′	cyclopropylmethyl	Me
199	OC(O)NR′	CH 2 CO 2 Me	Me
200	OC(O)NR′	CH 2 CH 2 NMe 2	Me
201	OC(O)NR′	CH 2 -(N-morpholinyl)	Me
202	OC(O)NR′	2-chloropyridin-5-yl-methyl	Me
203	OC(O)NR′	n-Hex	Me
204	OC(O)NR′	2-furanyl	Me
205	OC(O)NR′	2-pyrimidinyl	Me
206	OC(O)NR′	2-oxazolyl	Me
207	OC(O)NR′	5-[1,2,4]-oxadiazolyl	Me
208	OC(O)NR′	tetrazolyl	Me
209	OC(O)NR′	H	Et
210	OC(O)NR′	Me	Et
211	OC(O)NR′	Et	Et
212	OC(O)NR′	n-Pr	Et
213	OC(O)NR′	i-Pr	Et
214	OC(O)NR′	n-Bu	Et
215	OC(O)NR′	i-Bu	Et
216	OC(O)NR′	allyl	Et
217	OC(O)NR′	CH 2 C≡CH	Et
218	OC(O)NR′	CH═CH 2	Et
219	OC(O)NR′	CH 2 CH 2 F	Et
220	OC(O)NR′	CF 3	Et
221	OC(O)NR′	CH 2 CF 3	Et
222	OC(O)NR′	CH 2 CN	Et
223	OC(O)NR′	cyclopropyl	Et
224	OC(O)NR′	cyclopropylmethyl	Et
225	OC(O)NR′	CH 2 CO 2 Me	Et
226	OC(O)NR′	CH 2 CH 2 NMe 2	Et
227	OC(O)NR′	CH 2 -(N-morpholinyl)	Et
228	OC(O)NR′	2-chloropyridin-5-yl-methyl	Et
229	OC(O)NR′	2-furanyl	Et
230	OC(O)NR′	2-pyrimidinyl	Et
231	OC(O)NR′	2-oxazolyl	Et
232	OC(O)NR′	5-[1,2,4]-oxadiazolyl	Et
234	OC(O)NR′	tetrazolyl	Et
235	OC(O)NR′	n-Hex	Et
236	OC(O)C(O)O	cyclobutyl
237	OC(O)C(O)O	Me
238	OC(O)C(O)O	Et
239	OC(O)C(O)O	n-Pr
240	OC(O)C(O)O	i-Pr
241	OC(O)C(O)O	n-Bu
242	OC(O)C(O)O	i-Bu
243	OC(O)C(O)O	allyl
244	OC(O)C(O)O	CH 2 C≡CH
245	OC(O)C(O)O	CH═CH 2
246	OC(O)C(O)O	CH 2 CH 2 F
247	OC(O)C(O)O	CF 3
248	OC(O)C(O)O	CH 2 CF 3
249	OC(O)C(O)O	CH 2 CN
250	OC(O)C(O)O	cyclopropyl
251	OC(O)C(O)O	cyclopropylmethyl
252	OC(O)C(O)O	CH 2 CO 2 Me
253	OC(O)C(O)O	CH 2 CH 2 NMe 2
254	OC(O)C(O)O	CH 2 -(N-morpholinyl)
255	OC(O)C(O)O	2-chloropyridin-5-yl-methyl
256	OC(O)C(O)O	n-Hex
257	OC(O)C(O)O	furanyl
258	OC(O)C(O)O	2-pyrimidinyl
259	OC(O)C(O)O	2-oxazolyl
260	OC(O)C(O)O	5-[1,2,4]-oxadiazolyl
261	OC(O)C(O)O	tetrazolyl
262	S(O) 2 NR′	H	H
263	S(O) 2 NR′	Me	H
264	S(O) 2 NR′	Et	H
265	S(O) 2 NR′	n-Pr	H
266	S(O) 2 NR′	i-Pr	H
267	S(O) 2 NR′	n-Bu	H
268	S(O) 2 NR′	i-Bu	H
269	S(O) 2 NR′	allyl	H
270	S(O) 2 NR′	CH 2 C≡CH	H
271	S(O) 2 NR′	CH═CH 2	H
272	S(O) 2 NR′	CH 2 CH 2 F	H
273	S(O) 2 NR′	CF 3	H
274	S(O) 2 NR′	CH 2 CF 3	H
275	S(O) 2 NR′	CH 2 CN	H
276	S(O) 2 NR′	cyclopropyl	H
277	S(O) 2 NR′	cyclopropylmethyl	H
278	S(O) 2 NR′	CH 2 CO 2 Me	H
279	S(O) 2 NR′	CH 2 CH 2 NMe 2	H
280	S(O) 2 NR′	CH 2 -(N-morpholinyl)	H
281	S(O) 2 NR′	2-chloropyridin-5-yl-methyl	H
282	S(O) 2 NR′	n-Hex	H
283	S(O) 2 NR′	2-furanyl	H
284	S(O) 2 NR′	2-pyrimidinyl	H
285	S(O) 2 NR′	2-oxazolyl	H
286	S(O) 2 NR′	5-[1,2,4]-oxadiazolyl	H
287	S(O) 2 NR′	tetrazolyl	H
288	S(O) 2 NR′	H	Me
289	S(O) 2 NR′	Me	Me
290	S(O) 2 NR′	Et	Me
300	S(O) 2 NR′	n-Pr	Me
301	S(O) 2 NR′	i-Pr	Me
302	S(O) 2 NR′	n-Bu	Me
303	S(O) 2 NR′	i-Bu	Me
304	S(O) 2 NR′	allyl	Me
305	S(O) 2 NR′	CH 2 C≡CH	Me
306	S(O) 2 NR′	CH═CH 2	Me
307	S(O) 2 NR′	CH 2 CH 2 F	Me
308	S(O) 2 NR′	CF 3	Me
309	S(O) 2 NR′	CH 2 CF 3	Me
310	S(O) 2 NR′	CH 2 CN	Me
311	S(O) 2 NR′	cyclopropyl	Me
312	S(O) 2 NR′	cyclopropylmethyl	Me
313	S(O) 2 NR′	CH 2 CO 2 Me	Me
314	S(O) 2 NR′	CH 2 CH 2 NMe 2	Me
315	S(O) 2 NR′	CH 2 -(N-morpholinyl)	Me
316	S(O) 2 NR′	2-chloropyridin-5-yl-methyl	Me
317	S(O) 2 NR′	n-Hex	Me
318	S(O) 2 NR′	2-furanyl	Me
319	S(O) 2 NR′	2-pyrimidinyl	Me
320	S(O) 2 NR′	2-oxazolyl	Me
321	S(O) 2 NR′	5-[1,2,4]-oxadiazolyl	Me
322	S(O) 2 NR′	tetrazolyl	Me
323	S(O) 2 NR′	H	Et
324	S(O) 2 NR′	Me	Et
325	S(O) 2 NR′	Et	Et
326	S(O) 2 NR′	n-Pr	Et
327	S(O) 2 NR′	i-Pr	Et
328	S(O) 2 NR′	n-Bu	Et
329	S(O) 2 NR′	i-Bu	Et
330	S(O) 2 NR′	allyl	Et
331	S(O) 2 NR′	CH 2 C≡CH	Et
332	S(O) 2 NR′	CH═CH 2	Et
333	S(O) 2 NR′	CH 2 CH 2 F	Et
334	S(O) 2 NR′	CF 3	Et
335	S(O) 2 NR′	CH 2 CF 3	Et
336	S(O) 2 NR′	CH 2 CN	Et
337	S(O) 2 NR′	cyclopropyl	Et
338	S(O) 2 NR′	cyclopropylmethyl	Et
339	S(O) 2 NR′	CH 2 CO 2 Me	Et
340	S(O) 2 NR′	CH 2 CH 2 NMe 2	Et
341	S(O) 2 NR′	CH 2 -(N-morpholinyl)	Et
342	S(O) 2 NR′	2-chloropyridin-5-yl-methyl	Et
344	S(O) 2 NR′	n-Hex	Et
345	S(O) 2 NR′	2-furanyl	Et
346	S(O) 2 NR′	2-pyrimidinyl	Et
347	S(O) 2 NR′	2-oxazolyl	Et
348	S(O) 2 NR′	5-[1,2,4]-oxadiazolyl	Et
349	S(O) 2 NR′	tetrazolyl	Et

TABLE 5
Ex.				m.p.
No.	Y	R	R′	[° C.]
1	O	H
2	O	Me
3	O	Et
4	O	n-Pr
5	O	i-Pr
6	O	n-Bu
7	O	i-Bu
8	O	allyl
9	O	CH 2 C≡CH
10	O	CH═CH 2
11	O	CH 2 CH 2 F
12	O	CF 3
13	O	CH 2 CF 3
14	O	CH 2 CN
15	O	cyclopropyl
16	O	cyclopropylmethyl
17	O	CH 2 CO 2 Me
18	O	CH 2 CH 2 NMe 2
19	O	CH 2 -(N-morpholinyl)
20	O	2-chloropyridin-5-yl-methyl
21	O	n-Hex
22	O	2-furanyl
23	O	2-pyrimidinyl
24	O	2-oxazolyl
25	O	5-[1,2,4]-oxadiazolyl
26	O	tetrazolyl
27	S	H
28	S	Me
29	S	Et
30	S	n-Pr
31	S	i-Pr
32	S	n-Bu
33	S	i-Bu
33	S	allyl
34	S	CH 2 C≡CH
35	S	tetrazolyl
36	S	CH═CH 2
37	S	CH 2 CH 2 F
38	S	CF 3
39	S	CH 2 CF 3
40	S	CH 2 CN
41	S	cyclopropyl
42	S	cyclopropylmethyl
43	S	CH 2 CO 2 Me
44	S	CH 2 CH 2 NMe 2
45	S	CH 2 -(N-morpholinyl)
46	S	2-chloropyridin-5-yl-methyl
47	S	n-Hex
48	S	2-furanyl
49	S	2-pyrimidinyl
50	S	2-oxazolyl
51	S	5-[1,2,4]-oxadiazolyl
51a	S	tetrazolyl
52	S(O)	cyclobutyl
53	S(O)	Me
54	S(O)	Et
55	S(O)	n-Pr
56	S(O)	i-Pr
57	S(O)	n-Bu
58	S(O)	i-Bu
59	S(O)	allyl
60	S(O)	CH 2 C≡CH
61	S(O)	CH═CH 2
62	S(O)	CH 2 CH 2 F
63	S(O)	CF 3
64	S(O)	CH 2 CF 3
65	S(O)	CH 2 CN
66	S(O)	cyclopropyl
67	S(O)	cyclopropylmethyl
68	S(O)	CH 2 CO 2 Me
69	S(O)	CH 2 CH 2 NMe 2
70	S(O)	CH 2 -(N-morpholinyl)
71	S(O)	2-chloropyridin-5-yl-methyl
72	S(O)	n-Hex
73	S(O)	2-furanyl
74	S(O)	2-pyrimidinyl
75	S(O)	2-oxazolyl
76	S(O)	5-[1,2,4]-oxadiazolyl
77	S(O)	tetrazolyl
78	S(O) 2	cyclobutyl
79	S(O) 2	Me
80	S(O) 2	Et
81	S(O) 2	n-Pr
82	S(O) 2	i-Pr
83	S(O) 2	n-Bu
84	S(O) 2	i-Bu
85	S(O) 2	allyl
86	S(O) 2	CH 2 C≡CH
87	S(O) 2	CH═CH 2
88	S(O) 2	CH 2 CH 2 F
89	S(O) 2	CF 3
90	S(O) 2	CH 2 CF 3
91	S(O) 2	CH 2 CN
92	S(O) 2	cyclopropyl
93	S(O) 2	cyclopropylmethyl
94	S(O) 2	CH 2 CO 2 Me
95	S(O) 2	CH 2 CH 2 NMe 2
96	S(O) 2	CH 2 -(N-morpholinyl)
97	S(O) 2	2-chloropyridin-5-yl-methyl
98	S(O) 2	n-Hex
99	S(O) 2	2-furanyl
100	S(O) 2	2-pyrimidinyl
101	S(O) 2	2-oxazolyl
102	S(O) 2	5-[1,2,4]-oxadiazolyl
103	S(O) 2	tetrazolyl
104	OC(O)	H
105	OC(O)	Me
106	OC(O)	Et
107	OC(O)	n-Pr
108	OC(O)	i-Pr
109	OC(O)	n-Bu
110	OC(O)	i-Bu
111	OC(O)	allyl
112	OC(O)	CH 2 C≡CH
113	OC(O)	CH═CH 2
114	OC(O)	CH 2 CH 2 F
115	OC(O)	CF 3
116	OC(O)	CH 2 CF 3
117	OC(O)	CH 2 CN
118	OC(O)	cyclopropyl
119	OC(O)	cyclopropylmethyl
120	OC(O)	CH 2 CO 2 Me
121	OC(O)	CH 2 CH 2 NMe 2
122	OC(O)	CH 2 -(N-morpholinyl)
123	OC(O)	2-chloropyridin-5-yl-methyl
124	OC(O)	n-Hex
125	OC(O)	2-furanyl
126	OC(O)	2-pyrimidinyl
127	OC(O)	2-oxazolyl
128	OC(O)	5-[1,2,4]-oxadiazolyl
129	OC(O)	tetrazolyl
130	OC(O)O	cyclobutyl
131	OC(O)O	Me
132	OC(O)O	Et
133	OC(O)O	n-Pr
134	OC(O)O	i-Pr
135	OC(O)O	n-Bu
136	OC(O)O	i-Bu
137	OC(O)O	allyl
138	OC(O)O	CH 2 C≡CH
139	OC(O)O	CH═CH 2
140	OC(O)O	CH 2 CH 2 F
141	OC(O)O	CF 3
142	OC(O)O	CH 2 CF 3
143	OC(O)O	CH 2 CN
144	OC(O)O	cyclopropyl
145	OC(O)O	cyclopropylmethyl
146	OC(O)O	CH 2 CO 2 Me
147	OC(O)O	CH 2 CH 2 NMe 2
148	OC(O)O	CH 2 -(N-morpholinyl)
149	OC(O)O	2-chloropyridin-5-yl-methyl
150	OC(O)O	n-Hex
151	OC(O)O	2-furanyl
152	OC(O)O	2-pyrimidinyl
153	OC(O)O	2-oxazolyl
154	OC(O)O	5-[1,2,4]-oxadiazolyl
155	OC(O)O	tetrazolyl
156	OC(O)NR′	H	H
157	OC(O)NR′	Me	H
158	OC(O)NR′	Et	H
159	OC(O)NR′	n-Pr	H
160	OC(O)NR′	i-Pr	H
161	OC(O)NR′	n-Bu	H
162	OC(O)NR′	i-Bu	H
163	OC(O)NR′	allyl	H
164	OC(O)NR′	CH 2 C≡CH	H
165	OC(O)NR′	CH═CH 2	H
166	OC(O)NR′	CH 2 CH 2 F	H
167	OC(O)NR′	CF 3	H
168	OC(O)NR′	CH 2 CF 3	H
169	OC(O)NR′	CH 2 CN	H
170	OC(O)NR′	cyclopropyl	H
171	OC(O)NR′	cyclopropylmethyl	H
172	OC(O)NR′	CH 2 CO 2 Me	H
173	OC(O)NR′	CH 2 CH 2 NMe 2	H
174	OC(O)NR′	CH 2 -(N-morpholinyl)	H
175	OC(O)NR′	2-chloropyridin-5-yl-methyl	H
176	OC(O)NR′	n-Hex	H
177	OC(O)NR′	2-furanyl	H
178	OC(O)NR′	2-pyrimidinyl	H
179	OC(O)NR′	2-oxazolyl	H
180	OC(O)NR′	5-[1,2,4]-oxadiazolyl	H
181	OC(O)NR′	tetrazolyl	H
182	OC(O)NR′	H	Me
183	OC(O)NR′	Me	Me
184	OC(O)NR′	Et	Me
185	OC(O)NR′	n-Pr	Me
186	OC(O)NR′	i-Pr	Me
187	OC(O)NR′	n-Bu	Me
188	OC(O)NR′	i-Bu	Me
189	OC(O)NR′	allyl	Me
190	OC(O)NR′	CH 2 C≡CH	Me
200	OC(O)NR′	CH═CH 2	Me
201	OC(O)NR′	CH 2 CH 2 F	Me
202	OC(O)NR′	CF 3	Me
203	OC(O)NR′	CH 2 CF 3	Me
204	OC(O)NR′	CH 2 CN	Me
205	OC(O)NR′	cyclopropyl	Me
206	OC(O)NR′	cyclopropylmethyl	Me
207	OC(O)NR′	CH 2 CO 2 Me	Me
208	OC(O)NR′	CH 2 CH 2 NMe 2	Me
209	OC(O)NR′	CH 2 -(N-morpholinyl)	Me
210	OC(O)NR′	2-chloropyridin-5-yl-methyl	Me
211	OC(O)NR′	n-Hex	Me
212	OC(O)NR′	2-furanyl	Me
213	OC(O)NR′	2-pyrimidinyl	Me
214	OC(O)NR′	2-oxazolyl	Me
215	OC(O)NR′	5-[1,2,4]-oxadiazolyl	Me
216	OC(O)NR′	tetrazolyl	Me
217	OC(O)NR′	H	Et
218	OC(O)NR′	Me	Et
219	OC(O)NR′	Et	Et
220	OC(O)NR′	n-Pr	Et
221	OC(O)NR′	i-Pr	Et
222	OC(O)NR′	n-Bu	Et
223	OC(O)NR′	i-Bu	Et
224	OC(O)NR′	allyl	Et
225	OC(O)NR′	CH 2 C≡CH	Et
226	OC(O)NR′	CH═CH 2	Et
227	OC(O)NR′	CH 2 CH 2 F	Et
228	OC(O)NR′	CF 3	Et
229	OC(O)NR′	CH 2 CF 3	Et
230	OC(O)NR′	CH 2 CN	Et
231	OC(O)NR′	cyclopropyl	Et
232	OC(O)NR′	cyclopropylmethyl	Et
233	OC(O)NR′	CH 2 CO 2 Me	Et
234	OC(O)NR′	CH 2 CH 2 NMe 2	Et
235	OC(O)NR′	CH 2 -(N-morpholinyl)	Et
236	OC(O)NR′	2-chloropyridin-5-yl-methyl	Et
237	OC(O)NR′	n-Hex	Et
238	OC(O)NR′	2-furanyl	Et
239	OC(O)NR′	2-pyrimidinyl	Et
240	OC(O)NR′	2-oxazolyl	Et
241	OC(O)NR′	5-[1,2,4]-oxadiazolyl	Et
242	OC(O)NR′	tetrazolyl	Et
243	OC(O)C(O)O	cyclobutyl
244	OC(O)C(O)O	Me
245	OC(O)C(O)O	Et
246	OC(O)C(O)O	n-Pr
247	OC(O)C(O)O	i-Pr
248	OC(O)C(O)O	n-Bu
249	OC(O)C(O)O	i-Bu
250	OC(O)C(O)O	allyl
251	OC(O)C(O)O	CH 2 C≡CH
252	OC(O)C(O)O	CH═CH 2
253	OC(O)C(O)O	CH 2 CH 2 F
254	OC(O)C(O)O	CF 3
255	OC(O)C(O)O	CH 2 CF 3
256	OC(O)C(O)O	CH 2 CN
257	OC(O)C(O)O	cyclopropyl
258	OC(O)C(O)O	cyclopropylmethyl
259	OC(O)C(O)O	CH 2 CO 2 Me
260	OC(O)C(O)O	CH 2 CH 2 NMe 2
261	OC(O)C(O)O	CH 2 -(N-morpholinyl)
262	OC(O)C(O)O	2-chloropyridin-5-yl-methyl
263	OC(O)C(O)O	n-Hex
264	OC(O)C(O)O	2-furanyl
265	OC(O)C(O)O	2-pyrimidinyl
266	OC(O)C(O)O	2-oxazolyl
267	OC(O)C(O)O	5-[1,2,4]-oxadiazolyl
268	OC(O)C(O)O	tetrazolyl
269	S(O) 2 NR′	H	Me
270	S(O) 2 NR′	Me	Me
271	S(O) 2 NR′	Et	Me
272	S(O) 2 NR′	n-Pr	Me
273	S(O) 2 NR′	i-Pr	Me
274	S(O) 2 NR′	n-Bu	Me
275	S(O) 2 NR′	i-Bu	Me
276	S(O) 2 NR′	allyl	Me
277	S(O) 2 NR′	CH 2 C≡CH	Me
278	S(O) 2 NR′	CH═CH 2	Me
279	S(O) 2 NR′	CH 2 CH 2 F	Me
280	S(O) 2 NR′	CF 3	Me
281	S(O) 2 NR′	CH 2 CF 3	Me
282	S(O) 2 NR′	CH 2 CN	Me
283	S(O) 2 NR′	cyclopropyl	Me
284	S(O) 2 NR′	cyclopropylmethyl	Me
285	S(O) 2 NR′	CH 2 CO 2 Me	Me
286	S(O) 2 NR′	CH 2 CH 2 NMe 2	Me
287	S(O) 2 NR′	CH 2 -(N-morpholinyl)	Me
288	S(O) 2 NR′	2-chloropyridin-5-yl-methyl	Me
289	S(O) 2 NR′	n-Hex	Me
290	S(O) 2 NR′	2-furanyl	Me
291	S(O) 2 NR′	2-pyrimidinyl	Me
292	S(O) 2 NR′	2-oxazolyl	Me
293	S(O) 2 NR′	5-[1,2,4]-oxadiazolyl	Me
294	S(O) 2 NR′	tetrazolyl	Me
295	S(O) 2 NR′	H	Et
296	S(O) 2 NR′	Me	Et
297	S(O) 2 NR′	Et	Et
298	S(O) 2 NR′	n-Pr	Et
299	S(O) 2 NR′	i-Pr	Et
300	S(O) 2 NR′	n-Bu	Et
301	S(O) 2 NR′	i-Bu	Et
302	S(O) 2 NR′	allyl	Et
303	S(O) 2 NR′	CH 2 C≡CH	Et
304	S(O) 2 NR′	CH═CH 2	Et
305	S(O) 2 NR′	CH 2 CH 2 F	Et
306	S(O) 2 NR′	CF 3	Et
307	S(O) 2 NR′	CH 2 CF 3	Et
308	S(O) 2 NR′	CH 2 CN	Et
309	S(O) 2 NR′	cyclopropyl	Et
310	S(O) 2 NR′	cyclopropylmethyl	Et
311	S(O) 2 NR′	CH 2 CO 2 Me	Et
312	S(O) 2 NR′	CH 2 CH 2 NMe 2	Et
313	S(O) 2 NR′	CH 2 -(N-morpholinyl)	Et
314	S(O) 2 NR′	2-chloropyridin-5-yl-methyl	Et
315	S(O) 2 NR′	n-Hex	Et
316	S(O) 2 NR′	2-furanyl	Et
317	S(O) 2 NR′	2-pyrimidinyl	Et
318	S(O) 2 NR′	2-oxazolyl	Et
319	S(O) 2 NR′	5-[1,2,4]-oxadiazolyl	Et
320	S(O) 2 NR′	tetrazolyl	Et

TABLE 6
				m.p.
Ex. No.	Y	R	R′	[° C.]
1	O	H
2	O	Me
3	O	Et
4	O	n-Pr
5	O	i-Pr
6	O	n-Bu
7	O	i-Bu
8	O	allyl
9	O	CH 2 C≡CH
10	O	CH═CH 2
11	O	CH 2 CH 2 F
12	O	CF 3
13	O	CH 2 CF 3
14	O	CH 2 CN
15	O	cyclopropyl
16	O	cyclopropylmethyl
17	O	CH 2 CO 2 Me
18	O	CH 2 CH 2 NMe 2
19	O	CH 2 —(N-morpholinyl)
20	O	2-chloropyridin-5-yl-methyl
21	O	2-furanyl
22	O	2-pyrimidinyl
23	O	2-oxazolyl
24	O	5-[1,2,4]-oxadiazolyl
25	O	tetrazolyl
26	S	H
27	S	Me
28	S	Et
29	S	n-Pr
30	S	i-Pr
31	S	n-Bu
32	S	i-Bu
33	S	allyl
34	S	CH 2 C≡CH
35	S	CH═CH 2
36	S	CH 2 CH 2 F
37	S	CF 3
38	S	CH 2 CF 3
39	S	CH 2 CN
40	S	cyclopropyl
41	S	cyclopropylmethyl
42	S	CH 2 CO 2 Me
43	S	CH 2 CH 2 NMe 2
44	S	CH 2 —(N-morpholinyl)
45	S	2-chloropyridin-5-yl-methyl
46	S	2-furanyl
47	S	2-pyrimidinyl
48	S	2-oxazolyl
49	S	5-[1,2,4]-oxadiazolyl
50	S	tetrazolyl
51	S(O)	n-Hex
52	S(O)	Me
53	S(O)	Et
54	S(O)	n-Pr
55	S(O)	i-Pr
56	S(O)	n-Bu
57	S(O)	i-Bu
58	S(O)	allyl
59	S(O)	CH 2 C≡CH
60	S(O)	CH═CH 2
61	S(O)	CH 2 CH 2 F
62	S(O)	CF 3
63	S(O)	CH 2 CF 3
64	S(O)	CH 2 CN
65	S(O)	cyclopropyl
66	S(O)	cyclopropylmethyl
67	S(O)	CH 2 CO 2 Me
68	S(O)	CH 2 CH 2 NMe 2
69	S(O)	CH 2 —(N-morpholinyl)
70	S(O)	2-chloropyridin-5-yl-methyl
71	S(O)	2-furanyl
72	S(O)	2-pyrimidinyl
73	S(O)	2-oxazolyl
74	S(O)	5-[1,2,4]-oxadiazolyl
75	S(O)	tetrazolyl
76	S(O) 2	n-Hex
77	S(O) 2	Me
78	S(O) 2	Et
79	S(O) 2	n-Pr
80	S(O) 2	i-Pr
81	S(O) 2	n-Bu
82	S(O) 2	i-Bu
83	S(O) 2	allyl
84	S(O) 2	CH 2 C≡CH
85	S(O) 2	CH═CH 2
86	S(O) 2	CH 2 CH 2 F
87	S(O) 2	CF 3
88	S(O) 2	CH 2 CF 3
89	S(O) 2	CH 2 CN
90	S(O) 2	cyclopropyl
91	S(O) 2	cyclopropylmethyl
92	S(O) 2	CH 2 CO 2 Me
93	S(O) 2	CH 2 CH 2 NMe 2
94	S(O) 2	CH 2 —(N-morpholinyl)
95	S(O) 2	2-chloropyridin-5-yl-methyl
96	S(O) 2	2-furanyl
97	S(O) 2	2-pyrimidinyl
98	S(O) 2	2-oxazolyl
99	S(O) 2	5-[1,2,4]-oxadiazolyl
100	S(O) 2	tetrazolyl
101	OC(O)	H
102	OC(O)	Me
103	OC(O)	Et
104	OC(O)	n-Pr
105	OC(O)	i-Pr
106	OC(O)	n-Bu
107	OC(O)	i-Bu
108	OC(O)	allyl
109	OC(O)	CH 2 C≡CH
110	OC(O)	CH═CH 2
111	OC(O)	CH 2 CH 2 F
112	OC(O)	CF 3
113	OC(O)	CH 2 CF 3
114	OC(O)	CH 2 CN
115	OC(O)	cyclopropyl
116	OC(O)	cyclopropylmethyl
117	OC(O)	CH 2 CO 2 Me
118	OC(O)	CH 2 CH 2 NMe 2
119	OC(O)	CH 2 —(N-morpholinyl)
120	OC(O)	2-chloropyridin-5-yl-methyl
121	OC(O)	2-furanyl
122	OC(O)	2-pyrimidinyl
123	OC(O)	2-oxazolyl
124	OC(O)	5-[1,2,4]-oxadiazolyl
125	OC(O)	tetrazolyl
126	OC(O)O	n-Hex
127	OC(O)O	Me
128	OC(O)O	Et
129	OC(O)O	n-Pr
130	OC(O)O	i-Pr
131	OC(O)O	n-Bu
132	OC(O)O	i-Bu
133	OC(O)O	allyl
134	OC(O)O	CH 2 C≡CH
135	OC(O)O	CH═CH 2
136	OC(O)O	CH 2 CH 2 F
137	OC(O)O	CF 3
138	OC(O)O	CH 2 CF 3
139	OC(O)O	CH 2 CN
140	OC(O)O	cyclopropyl
141	OC(O)O	cyclopropylmethyl
142	OC(O)O	CH 2 CO 2 Me
143	OC(O)O	CH 2 CH 2 NMe 2
144	OC(O)O	CH 2 —(N-morpholinyl)
145	OC(O)O	2-chloropyridin-5-yl-methyl
146	OC(O)O	2-furanyl
147	OC(O)O	2-pyrimidinyl
148	OC(O)O	2-oxazolyl
149	OC(O)O	5-[1,2,4]-oxadiazolyl
150	OC(O)O	tetrazolyl
151	OC(O)NR′	H	H
152	OC(O)NR′	Me	H
153	OC(O)NR′	Et	H
154	OC(O)NR′	n-Pr	H
155	OC(O)NR′	i-Pr	H
156	OC(O)NR′	n-Bu	H
157	OC(O)NR′	i-Bu	H
158	OC(O)NR′	allyl	H
159	OC(O)NR′	CH 2 C≡CH	H
160	OC(O)NR′	CH═CH 2	H
161	OC(O)NR′	CH 2 CH 2 F	H
162	OC(O)NR′	CF 3	H
163	OC(O)NR′	CH 2 CF 3	H
164	OC(O)NR′	CH 2 CN	H
165	OC(O)NR′	cyclopropyl	H
166	OC(O)NR′	cyclopropylmethyl	H
167	OC(O)NR′	CH 2 CO 2 Me	H
168	OC(O)NR′	CH 2 CH 2 NMe 2	H
169	OC(O)NR′	CH 2 —(N-morpholinyl)	H
170	OC(O)NR′	2-chloropyridin-5-yl-methyl	H
171	OC(O)NR′	2-furanyl	H
172	OC(O)NR′	2-pyrimidinyl	H
173	OC(O)NR′	2-oxazolyl	H
174	OC(O)NR′	5-[1,2,4]-oxadiazolyl	H
175	OC(O)NR′	tetrazolyl	H
176	OC(O)NR′	H	Me
177	OC(O)NR′	Me	Me
178	OC(O)NR′	Et	Me
179	OC(O)NR′	n-Pr	Me
180	OC(O)NR′	i-Pr	Me
181	OC(O)NR′	n-Bu	Me
182	OC(O)NR′	i-Bu	Me
183	OC(O)NR′	allyl	Me
184	OC(O)NR′	CH 2 C≡CH	Me
185	OC(O)NR′	CH═CH 2	Me
186	OC(O)NR′	CH 2 CH 2 F	Me
187	OC(O)NR′	CF 3	Me
188	OC(O)NR′	CH 2 CF 3	Me
189	OC(O)NR′	CH 2 CN	Me
190	OC(O)NR′	cyclopropyl	Me
191	OC(O)NR′	cyclopropylmethyl	Me
192	OC(O)NR′	CH 2 CO 2 Me	Me
193	OC(O)NR′	CH 2 CH 2 NMe 2	Me
194	OC(O)NR′	CH 2 —(N-morpholinyl)	Me
195	OC(O)NR′	2-chloropyridin-5-yl-methyl	Me
196	OC(O)NR′	furanyl	Me
197	OC(O)NR′	2-pyrimidinyl	Me
198	OC(O)NR′	2-oxazolyl	Me
199	OC(O)NR′	5-[1,2,4]-oxadiazolyl	Me
200	OC(O)NR′	tetrazolyl	Me
201	OC(O)NR′	H	Et
202	OC(O)NR′	Me	Et
203	OC(O)NR′	Et	Et
204	OC(O)NR′	n-Pr	Et
205	OC(O)NR′	i-Pr	Et
206	OC(O)NR′	n-Bu	Et
207	OC(O)NR′	i-Bu	Et
208	OC(O)NR′	allyl	Et
209	OC(O)NR′	CH 2 C≡CH	Et
210	OC(O)NR′	CH═CH 2	Et
211	OC(O)NR′	CH 2 CH 2 F	Et
212	OC(O)NR′	CF 3	Et
213	OC(O)NR′	CH 2 CF 3	Et
214	OC(O)NR′	CH 2 CN	Et
215	OC(O)NR′	cyclopropyl	Et
216	OC(O)NR′	cyclopropylmethyl	Et
217	OC(O)NR′	CH 2 CO 2 Me	Et
218	OC(O)NR′	CH 2 CH 2 NMe 2	Et
219	OC(O)NR′	CH 2 —(N-morpholinyl)	Et
220	OC(O)NR′	2-chloropyridin-5-yl-methyl	Et
221	OC(O)NR′	2-furanyl	Et
222	OC(O)NR′	2-pyrimidinyl	Et
223	OC(O)NR′	2-oxazolyl	Et
224	OC(O)NR′	5-[1,2,4]-oxadiazolyl	Et
225	OC(O)NR′	tetrazolyl	Et
226	OC(O)C(O)O	n-Hex
227	OC(O)C(O)O	Me
228	OC(O)C(O)O	Et
229	OC(O)C(O)O	n-Pr
230	OC(O)C(O)O	i-Pr
231	OC(O)C(O)O	n-Bu
232	OC(O)C(O)O	i-Bu
233	OC(O)C(O)O	allyl
234	OC(O)C(O)O	CH 2 C≡CH
235	OC(O)C(O)O	CH═CH 2
236	OC(O)C(O)O	CH 2 CH 2 F
237	OC(O)C(O)O	CF 3
238	OC(O)C(O)O	CH 2 CF 3
239	OC(O)C(O)O	CH 2 CN
240	OC(O)C(O)O	cyclopropyl
241	OC(O)C(O)O	cyclopropylmethyl
242	OC(O)C(O)O	CH 2 CO 2 Me
243	OC(O)C(O)O	CH 2 CH 2 NMe 2
244	OC(O)C(O)O	CH 2 —(N-morpholinyl)
245	OC(O)C(O)O	2-chloropyridin-5-yl-methyl
246	OC(O)C(O)O	2-furanyl
247	OC(O)C(O)O	2-pyrimidinyl
248	OC(O)C(O)O	2-oxazolyl
249	OC(O)C(O)O	5-[1,2,4]-oxadiazolyl
250	OC(O)C(O)O	tetrazolyl
251	S(O) 2 NR′	H	H
252	S(O) 2 NR′	Me	H
253	S(O) 2 NR′	Et	H
254	S(O) 2 NR′	n-Pr	H
255	S(O) 2 NR′	i-Pr	H
256	S(O) 2 NR′	n-Bu	H
257	S(O) 2 NR′	i-Bu	H
258	S(O) 2 NR′	allyl	H
259	S(O) 2 NR′	CH 2 C≡CH	H
260	S(O) 2 NR′	CH═CH 2	H
261	S(O) 2 NR′	CH 2 CH 2 F	H
262	S(O) 2 NR′	CF 3	H
263	S(O) 2 NR′	CH 2 CF 3	H
264	S(O) 2 NR′	CH 2 CN	H
265	S(O) 2 NR′	cyclopropyl	H
266	S(O) 2 NR′	cyclopropylmethyl	H
267	S(O) 2 NR′	CH 2 CO 2 Me	H
268	S(O) 2 NR′	CH 2 CH 2 NMe 2	H
269	S(O) 2 NR′	CH 2 —(N-morpholinyl)	H
270	S(O) 2 NR′	2-chloropyridin-5-yl-methyl	H
271	S(O) 2 NR′	2-furanyl	H
272	S(O) 2 NR′	2-pyrimidinyl	H
273	S(O) 2 NR′	2-oxazolyl	H
274	S(O) 2 NR′	5-[1,2,4]-oxadiazolyl	H
275	S(O) 2 NR′	tetrazolyl	H
276	S(O) 2 NR′	H	Me
277	S(O) 2 NR′	Me	Me
278	S(O) 2 NR′	Et	Me
279	S(O) 2 NR′	n-Pr	Me
280	S(O) 2 NR′	i-Pr	Me
281	S(O) 2 NR′	n-Bu	Me
282	S(O) 2 NR′	i-Bu	Me
283	S(O) 2 NR′	allyl	Me
284	S(O) 2 NR′	CH 2 C≡CH	Me
285	S(O) 2 NR′	CH═CH 2	Me
286	S(O) 2 NR′	CH 2 CH 2 F	Me
287	S(O) 2 NR′	CF 3	Me
288	S(O) 2 NR′	CH 2 CF 3	Me
289	S(O) 2 NR′	CH 2 CN	Me
290	S(O) 2 NR′	cyclopropyl	Me
291	S(O) 2 NR′	cyclopropylmethyl	Me
292	S(O) 2 NR′	CH 2 CO 2 Me	Me
293	S(O) 2 NR′	CH 2 CH 2 NMe 2	Me
294	S(O) 2 NR′	CH 2 —(N-morpholinyl)	Me
295	S(O) 2 NR′	2-chloropyridin-5-yl-methyl	Me
296	S(O) 2 NR′	2-furanyl	Me
297	S(O) 2 NR′	2-pyrimidinyl	Me
298	S(O) 2 NR′	2-oxazolyl	Me
299	S(O) 2 NR′	5-[1,2,4]-oxadiazolyl	Me
300	S(O) 2 NR′	tetrazolyl	Me
301	S(O) 2 NR′	H	Et
302	S(O) 2 NR′	Me	Et
303	S(O) 2 NR′	Et	Et
304	S(O) 2 NR′	n-Pr	Et
305	S(O) 2 NR′	i-Pr	Et
306	S(O) 2 NR′	n-Bu	Et
307	S(O) 2 NR′	i-Bu	Et
308	S(O) 2 NR′	allyl	Et
309	S(O) 2 NR′	CH 2 C≡CH	Et
310	S(O) 2 NR′	CH═CH 2	Et
311	S(O) 2 NR′	CH 2 CH 2 F	Et
312	S(O) 2 NR′	CF 3	Et
313	S(O) 2 NR′	CH 2 CF 3	Et
314	S(O) 2 NR′	CH 2 CN	Et
315	S(O) 2 NR′	cyclopropyl	Et
316	S(O) 2 NR′	cyclopropylmethyl	Et
317	S(O) 2 NR′	CH 2 CO 2 Me	Et
318	S(O) 2 NR′	CH 2 CH 2 NMe 2	Et
319	S(O) 2 NR′	CH 2 —(N-morpholinyl)	Et
320	S(O) 2 NR′	2-chloropyridin-5-yl-methyl	Et
321	S(O) 2 NR′	2-furanyl	Et
322	S(O) 2 NR′	2-pyrimidinyl	Et
323	S(O) 2 NR′	2-oxazolyl	Et
324	S(O) 2 NR′	5-[1,2,4]-oxadiazolyl	Et
325	S(O) 2 NR′	tetrazolyl	Et

B. Formulation Examples

a) A dusting powder is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc, as inert substance, and comminuting the mixture in an impact mill.

b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of active compound, 65 parts by weight of kaolin-containing quartz, as the inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurinate, as wetting and dispersing agent, and grinding the mixture in a pinned disk mill.

c) A dispersion concentrate which is readily dispersible in water is prepared by mixing 40 parts by weight of active compound with 7 parts by weight of a sulfosuccinic monoester, 2 parts by weight of a sodium ligninsulfonate and 51 parts by weight of water and grinding the mixture to a fineness of below 5 microns in a grinding bead mill.

d) An emulsifiable concentrate can be prepared from 15 parts by weight of active compound, 75 parts by weight of cyclohexane, as the solvent, and 10 parts by weight of ethoxylated nonylphenol (10 EO), as the emulsifier.

e) Granules can be prepared from 2 to 15 parts by weight of active compound and an inert granule carrier material, such as attapulgite, pumice granules and/or quartz sand. A suspension of the wettable powder from Example b) having a solids content of 30% is expediently used, and this is sprayed onto the surface of attapulgite granules and the components are dried and mixed intimately. The weight content of the wettable powder is approximately 5% and that of the inert carrier material is approximately 95% of the finished granules.

C. Biological Examples

Example 1

Germinated broad bean seeds ( Vicia faba ) with radicles were transferred into brown glass bottles filled with tap water and subsequently populated with approximately 100 black bean aphids ( Aphis fabae ). Plants and aphids were then dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution had dripped off, plants and animals were kept in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity). After 3 and 6 days storage, the effect of the preparation on the aphids was determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Example Nos. 2/29, 2/43, 2/67, 2/6, 3/6, 3/50, 3/75 and 3/49 effected a mortality of 90-100% among the aphids.

The compounds are numbered with the Table/No. in the table.

Example 2

The leaves of 12 rice plants having a stem length of 8 cm were dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution had dripped off, the rice plants treated in this manner were placed in a Petri dish and populated with approximately 20 larvae (L3 stage) of the rice leafhopper species Nilaparvata lugens . The Petri dish was closed and stored in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity). After 6 days storage, the mortality among the leafhopper larvae was determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Example Nos. 2/97, 2/127, 2/153, 2/255, 3/50 and 3/75 effected a mortality of 90-100%.

Example 3

Germinated broad bean seeds ( Vicia faba ) with radicles were transferred into brown glass bottles filled with tap water. Four milliliters of an aqueous solution of the formulated preparation to be examined were pipetted into the brown glass bottle. The broad bean was subsequently heavily populated with approximately 100 black bean aphids ( Aphis fabae ). Plants and animals were then stored in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity). After 3 and 6 days storage, the root-systemic activity of the preparation on the aphids was determined. At a concentration of 30 ppm (based on the content of active compound), the preparations of Example Nos. 2/29, 2/43, 2/55, 2/67, 2/97, 2/6, 2/167, 2/153, 3/6, 3/50, 3/75 and 3/49 effected a mortality of 90-100% among the aphids by root-systemic action.

Although preferred embodiments of the present invention and modifications thereof have been described in detail herein, it is to be understood that this invention is not limited to those precise embodiments and modifications, and that other modifications and variations may be affected by one skilled in the art without departing from the spirit and scope of the invention as defined by the appended claims.

Claims

1. A 4-trifluoromethyl-3-oxadiazolylpyridine of the formula (I′), or a salt thereof, whereinm is 0 or 1; X′ is a single bond, a straight-chain alkylene group having 1, 2 or 3 carbon atoms or a branched alkylene group having 3 to 9 carbon atoms, where one or more H atoms may be replaced by F; Y′ is —O—, —S—, —SO2—, —O—CO—, —O—CO—O—, —SO2—O—, —O—SO2—, —NR1—, —NR2—CO—, —NR3—CO—O—, —NR4—CO—NR5—, —O—CO—CO—O—, —O—CO—NR6—, —SO2—NR7— or —NR8—SO2—; R,R1,R2,R3,R4,R5,R6,R7,R8 are identical or different and are independently of one another H, (C1-C10)-alkyl, (C2-C10)-alkenyl, (C2-Cl10)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C6-C8)-cycloalkynyl, heterocyclyl or —(CH2)1-4-heterocyclyl, where each of the eight last-mentioned groups is unsubstituted or mono- or polysubstituted, and where, optionally R and R1, R and R2, R and R5, R and R6, R and R7, R and R8 or X′ and R, together form a ring system, with the proviso, that the compounds in which X′=-, Y′=O, R=H X′=-, Y′=O, R=Me X′=-, Y′=O, R=Et X′=-, Y′=O, R=CHF2 X′=-, Y′=O, R=CH2Ph X′=CH2, Y′=O, R=2-furanyl X′=CH2, Y′=O, R=Me X′=CH2, Y′=O, R=5-isoxazolyl X′=CH2, Y′=O, R=5-nitrofuran-2-yl X′=CH2CH2, Y′=O, R=H X′=CH2CH2; Y′=O, R=Me X′=CH2CH2, Y′=O, X′=CH2CH2, Y′=O, R=Et X′=CH2CH2, Y′=O, X′=CH2CH2; Y′=OC(O), R=4-F-phenyl X′=CH2CH2, Y′=OC(O), R=2,6-difluorophenyl X′=CH2CH2, Y′=OC(O), R=4-nitrophenyl X′=CH2CH2, Y′=OC(O), R=t-Bu X′=CH2CH2, Y′=OC(O), R=cyclopropyl X′=CH2CH2, Y′=OC(O), R=Me X′=CH2CH2CH2, Y′=O, R=H X′=-, Y′=S(O), R=4-bromobenzyl X′=CH2, Y′=S, R=Me X′=CH2, Y′=S(O), R=Me X′=CH2, Y′=S(O)2, R=t-Bu X′=CH2, Y′=S, R=2-thienyl X′=CH2CH2, Y′=S, R=Me X′=CH2CH2, Y′=S, R=n-Pr X′=CH2CH2, Y′=S, R=benzyl X′=CH2CH2, Y′=S, R=2-thienylmethyl X′=CH2CH2CH2, Y′=S, R=Me X′=CH2CH2CH2, Y′=SO, R=Me X′=CH2CH2CH2CH2, Y′=S, R=CH2CH2CH2CH2OMe are not included.

2. The 4-trifluoromethyl-3-oxadiazolylpyridine as claimed in claim 1, wherein m in the formula (I′) is 0.

3. The 4-trifluoromethyl-3-oxadiazolylpyridine as claimed in claim 1, wherein X′ in the formula (I′) is a single bond, —CH2—, —CH2—CH2—, —CH2—CH(CH3)— or —CH2—C(CH3)2—.

4. The 4-trifluoromethyl-3-oxadiazolylpyridine as claimed in claim 1, wherein Y′ in the formula (I′) is —O—, —S—, —SO—, —SO2—, —O—CO—, —O—CO—O—, —O—CO—NR6—, —SO2—NR7—, —O—SO2— or —SO2—O—.

5. A process for preparing a compound of the formula (I′) as claimed in claim 1, comprising reacting an activated derivative of an acid of the formula (II), in the presence of a base with a compound of the formula (III), in which the radical —X′—Y′—R is as defined in formula (I′), or is a precursor of a radical defined therein.

6. A composition having insecticidal, acaricidal and/or nematicidal action, which comprises at least one compound as claimed in claim 1.

7. The composition as claimed in claim 6, further comprising a carrier substance and/or a surface-active substance.

8. The composition as claimed in claim 6, further comprising an active compound from the group of acaricides, fungicides, herbicides, insecticides, nematicides or growth-regulating substances.

9. A veterinary composition for treatment of a patient in need thereof, comprising the compound of claim 1 or the composition of claim 6.

10. A method for controlling harmful insects, acarids and nematodes, which comprises applying an effective amount of the compound as claimed in claim 1 or the composition as claimed in claim 6 to the site of the desired action.

11. A method for protecting useful plants against the undesirable action of harmful insects, acarids and nematodes, which comprises treating the seed of the useful plant with at least one compound as claimed in claim 1 or at least one composition as claimed in claim 6.

12. A method of controlling harmful insects, acarids and nematodes in useful plants, comprising applying an effective amount of the compound of claim 1 or the composition of claim 6 to said useful plant.