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

FIELD OF THE INVENTION

[0002] 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

[0003] 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.

[0004] 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.

[0005] WO-A-98/57969, which is not prepublished, proposes 4-haloalkylpyridines and -pyrimidines for use as pesticides.

[0006] 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

[0007] a) in position 5 and is optionally substituted by a thiomethyl group in position 2, or

[0008] b) in position 2 and is optionally substituted in position 4 and 6, in each case by a methyl group.

[0009] 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:

[0010] 3-(2-chlorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole

[0011] 3-(2,6-difluorophenyl)-1-methyl-5-(4-rifluoromethyl-3-pyridyl)-1H-1,2,4-triazole and

[0012] 3-(2-chloro-4-fluorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole,

[0013] their desired activity at low application rates, however, is not always satisfactory, especially when controlling insects and spider mites.

[0014] Some commercially available 4-haloalkyl-3-heterocyclylpyridines are known from the Maybridge Catalogue 1996/1997, Maybridge Chemical CO. LTD., Trevillett Tintagel, GB:

[0015] 3-(3,5-dichlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0016] 5-(4-trifluoromethyl-3-pyridyl)-3-phenyl-1,2,4-oxadiazole

[0017] 3-(4-trifluoromethyl-3-pyridyl)-5-phenyl-1,2,4-oxadiazole

[0018] 5-(2-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0019] 5-(3-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0020] 5-(4-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0021] 5-(2-fluorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0022] 5-(4-fluorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0023] 5-(2,4-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0024] 5-(3,4-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0025] 5-(3,5-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0026] 5-(2,6-dichloro-4-pyridyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0027] 5-(3,5-bistrifluoromethylphenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0028] 2-(2-chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole

[0029] 2-(3-chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole

[0030] 2-(4-chlorophenyl)-5-( 4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole

[0031] 2-(2-trifluoromethoxyphenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole

[0032] 2-(4-trifluoromethoxyphenyl )-5-(4-trifluoromethyl -3-pyridyl)-1,3,4-oxadiazole

[0033] 2-(4-trifluoromethyl-3-pyridyl)-5-phenyl-1,3,4-oxadiazole

[0034] 2-(4-trifluoromethyl-3-pyridyl)-4-methylthiazolecarbohydrazide

[0035] ethyl 2-(4-trifluoromethyl-3-pyridyl)-4-methylthiazolecarboxylate

[0036] N-(4-chlorophenyl)carbonyl-N′-[2-(4-trifluoromethyl-3-pyridyl)-4-methyl-5-thiazolyl]carbonylhydrazine

[0037] 2-(4-trifluoromethyl-3-pyridyl)-4-thiazolecarbohydrazide

[0038] 4-(4-chlorophenyl)-2-(4-trifluoromethyl-3-pyridyl)thiazole

[0039] 4-(4-cyanophenyl)-2-(4-trifluoromethyl-3-pyridyl)thiazole

[0040] N-(4-trifluoromethylphenyl)carbonyl-N′-[2-(4-trifluoromethyl-3-pyridyl)-4-thiazolyl]carbonylhydrazine

[0041] 2-(2-(4-trifluoromethyl-3-pyridyl)thiazolyl)-5-chloro-3-methylbenzo[b]thiophene

[0042] 2-(4-chlorophenylmethylthio)-5-(4-trifluoromethyl-3-pyridyl)-1-methyl-1H-1,3,4-triazole

[0043] 2-(4-chlorophenylcarbonylmethylthio)-5-(4-trifluoromethyl-3-pyridyl)-1-methyl-1H-1,3,4-triazole and

[0044] 2-ethoxycarbonylmethylthio-5-(4-trifluoromethyl-3-pyridyl)-1-methyl-1H-1,3 ,4-triazole.

[0045] However, a biological activity toward harmful organisms has hitherto not been disclosed.

SUMMARY OF THE INVENTION

[0046] 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

[0047] 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.

[0048] In the formula (I):

[0049] Y is halo-C1-C6-alkyl;

[0050] X is CH or N;

[0051] m is 0 or 1;

[0052] Q is a 5-membered heterocyclic group

[0053] in which

[0054] a) X1=W, X2=NRa, X=CRbR1 or

[0055] b) X1=NRa, X2=CRbR1, X3=W or

[0056] c) X1=V, X2=CRaR1, X3=NRb or

[0057] d) X1=V, X2=CRaR2, X3=CRbR3 or

[0058] e) X1=V, X2=CR4R5, X3=CR6R7 or

[0059] f) X1=NRa, X2=CRbR1, X3=NR8;

[0060] Ra and Rb together are a bond

[0061] V is oxygen, sulfur or NR9;

[0062] W is oxygen or sulfur;

[0063] R1 is hydrogen,

[0064] (C1-C20)-alkyl, (C2-C20)-alkenyl, (C2-C20)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C6-C8)-cycloalkynyl,

[0065] where the six last-mentioned radicals are optionally substituted by one or more radicals from the group

[0066] halogen, cyano, nitro, hydroxyl, —C(═W)R10, —C(═NOR10)R10,

[0067] —C(═NNR102)R10, —C(═W)OR10, —C(═W)NR102, —OC(═W)R10, —OC(═W)OR10,

[0068] —NR10C(═W)R10, —N[C(═W)R10]2, —NR10C(═W)OR10, —C(═W)NR10—NR102,

[0069] —C(═W)NR10—NR10[C(═W)R10],

[0070] —NR10—C(═W)NR102, —NR10—NR10C(═W)R10, —NR10—N[C(═W)R10]2,

[0071] —N[(C═W)R10]-NR102,

[0072] —NR10—NR10[(C═W)R10], —NR10—NR10[(C═W)WR10],

[0073] —NR10—R10[(C═W)NR102], —NR10(C═NR10)R10, —NR10(C═NR10)NR102,

[0074] O-NR102, —O—NR10(C═W)R10, —SO2NR102, -NR10SO2R10, —SO2OR10,

[0075] —OSO2R10, —OR10, —NR102, —SR10, SiR103, —SeR10, —PR102, —P(═W)R102,

[0076] —SOR10, —SO2R10, —PW2R102, —PW3R102, aryl and heterocyclyl,

[0077] the two last-mentioned radicals optionally being substituted by one or more radicals from the group

[0078] (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C6-C8)-cycloalkynyl, (C1-C6)-haloalkyl, (C2-C6)-haloalkenyl, (C2-C6)-haloalkynyl, halogen, —OR10, —NR102, —SR10, —SiR103, —C(═W)R10, —C(═W)OR10, —C(═W)NR102, —SOR10, —SO2R10, nitro, cyano and hydroxyl,

[0079] aryl,

[0080] which is optionally substituted by one or more radicals from the group

[0081] (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl and (C6-C8)-cycloalkynyl,

[0082] where these six abovementioned radicals are optionally substituted by one or more radicals from the group

[0083] halogen, cyano, nitro, —C(═W)R10, —C(═W)OR10, —C(═W)NR102, —OR10, —NR102, —SR10, —SOR10 and —SO2R10,

[0084] halogen, cyano, nitro, —C(═W)R10, —C(═NOR10)R10, —C(═NNR102)R10, —C(═W)OR10, —C(═W)NR102, —OC(═W)R10, —OC(═W)OR10, —NR10C(═W)R10, N[C(═W)R10]2, —NR10C(═W)OR10, —OR10, —NR102, —SR10, —SiR103, PR102, —SOR10, —SO2R10, —PW2R102 and —PW3R102,

[0085] heterocyclyl,

[0086] which is optionally substituted by one or more radicals from the group

[0087] (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl and (C6-C8)-cycloalkynyl,

[0088] where the six abovementioned radicals are optionally substituted by one or more radicals from the group

[0089] cyano, nitro, halogen, —C(═W)R10, —C(═W)OR10, —C(═W)NR102,

[0090] —NR10C(═W)R10, —N[C(═W)R10]2, —OC(═W)R10, —OC(═W)OR10, —OR10, —NR102, —SR10, —SOR10 and —SO2R10;

[0091] halogen, cyano, nitro, —C(═W)R10, —C(═W)OR10, —C(═W)NR102, —OC(═W)R10, —OR10, —NR102, —SR10, —SOR10 and —SO2R10; —OR10, —NR102, —SR10, —SOR10, —SO2R10, —C(═W)R10, —C(═NOR10)R10, —C(═NNR102)R10, —C(═W)OR10, —C(═W)NR102, —OC(═W)R10, —OC(═W)OR10, —NR10C(═W)R10, —N[C(═W)R10]2, —NR10C(═W)OR10, —C(═W)NR10—NR102, —C(═W)NR10—NR10[C(═W)R10], —NR10—C(═W)NR102, —NR10—NR10C(═)W)R10, —NR10—NC(═W)R102, —N(C═W)R10—NR102, —NR10—NR10[(C═W)R10], —NR10—NR10[(C═W)WR10], —NR10—NR10[(C═W)NR102], —NR10(C═NR10)R10, —NR10(C═NR10)NR102, —O—NR102, —O—NR10(C═W)R10, —SO2NR102, —NR10SO2R10, —SO2OR10, —OSO2R10, —SC(═W)R10, —SC(═W)OR10, —SC(═W)R10, —PR102, —PW2R102, —PW3R102, SiR103 or halogen;

[0092] R2 and R3 independently of one another have the definitions given in R1;

[0093] R2 and R3 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 R1; R4 and R6 independently of one another have the definitions given in R1;

[0094] R4 and R6 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 R1;

[0095] R5 and R7 independently of one another are hydrogen,

[0096] (C1-C20)-alkyl, (C2-C20)-alkenyl, (C2-C20)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C6-C8)-cycloalkynyl,

[0097] where the six last-mentioned radicals are optionally substituted by one or more radicals from the group

[0098] halogen, cyano, nitro, hydroxyl, —C(═W)R10, —C(═NOR10)R10, —C(═NNR102)R10, —C(═W)OR10, —C(═W)NR102, —OC(═W)R10, OC(═W)OR10, —NR10C(═W)R10, —N[C(═W)R10]2, —NR10C(═W)OR10, —C(═W)NR10—NR102, —C(═W)NR10—NR10[C(═W)R10], —NR10—C(═W)NR102, —NR10—NR10C(═W)R10, —NR10—N[C(═W)R10]2, —N[(C═W)R10]—NR102, —NR10—NR10[(C═W)R10], —NR10—NR10[(C═W)WR10], —NR10—NR10[(C═W)NR102], —NR10(C═NR10)R10, —NR10(C═NR10)NR102, —O—NR102, —O—NR10(C═W)R10, —OR10, —NR102, —SR10, —SiR103, —SeR10, —PR102, —P(═W)R102, —SOR10, —SO2R10, —PW2R102, —PW3R102, aryl and heterocyclyl, of which the two mentioned last are optionally substituted by one or more radicals from the group

[0099] (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C6-C8)-cycloalkynyl, (C1-C6)-haloalkyl, (C2-C6)-haloalkenyl, (C2-C6)-haloalkynyl, halogen, —OR10, —NR102, —SR10, —SiR103, —C(═W)R10, —C(═W)OR10, —C(═W)NR102, —SOR10, —SO2R10, nitro, cyano and hydroxyl,

[0100] aryl,

[0101] which is optionally substituted by one or more radicals from the group (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl and (C6-C8)-cycloalkynyl,

[0102] where these six abovementioned radicals are optionally substituted by one or more radicals from the group

[0103] halogen, cyano, nitro, —C(═W)R10, —C(═W)OR10, —C(═W)NR102, —OR10, —NR102, —SR10, —SOR10and —SO2R10;

[0104] halogen, cyano, nitro, —C(═W)R10, —C(═NOR10)R10, —C(═NNR102)R10, —C(═W)OR10, —C(═W)NR102, —OC(═W)R10, —OC(═W)OR10, NR10C(═W)R10, —N[C(═W)R10]2, —NR10C(═W)OR10, —OR10, NR102, —SR10, —SiR103,—PR102, —SOR10, —SO2R10, —PW2R102 and —PW3R102;

[0105] pyridyl,

[0106] which is optionally substituted by one or more radicals from the group

[0107] (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl and (C6-C8)-cycloalkynyl, where the six abovementioned radicals are optionally substituted by one or more radicals from the group

[0108] cyano, nitro, halogen, —C(═W)R10, —C(═W)OR10, —C(═W)NR102, —OR10, —NR102, —SR10, —SOR10 and —SO2R10,

[0109] halogen, cyano, nitro, —C(═W)R10, —C(═W)OR10, —C(═W)NR102, —OC(═W)R10, —OR10, —NR102, —SR10, —SOR10and —SO2R10; —C(═W)R10, —C(═NOR10)R10, —C(═NNR102)R10, —C(═W)OR10, —C(═W)NR102 or halogen;

[0110] R4 and R5 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 R1;

[0111] R4 and R5 together form one of the groups ═O, ═S or ═N—R9;

[0112] R6 and R7 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 R1;

[0113] R6 and R7 together form one of the groups ═O, ═S or ═N—R9;

[0114] R8 is hydrogen,

[0115] (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)—cycloalkenyl, (C3-C8)-cycloalkyl-(C1-C4)-alkyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenyl, (C3-C6)-alkyl-(C3-C8)-cycloalkyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkyl, (C2-C6)-alkynyl-(C3-C8)-cycloalkyl, (C1-C6)-alkyl-(C4-C8)-cycloalkenyl, (C2-C6)-alkenyl-(C4-C8)-cycloalkenyl,

[0116] where the fourteen last-mentioned radicals are optionally substituted by one or more radicals from the group

[0117] halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C1-C6)-haloalkyloxy, (C2-C6)-haloalkenyloxy, (C2-C6)-haloalkynyloxy, (C3-C8)-cycloalkoxy, (C4-C8)-cycloalkenyloxy, (C3-C8)-halocycloalkoxy, (C4-C8)-halocycloalkenyloxy, (C3-C8)-cycloalkyl-(C1-C4)-alkoxy, (C4-C8)-cycloalkenyl-(C1-C4)-alkoxy, (C3-C8)-cycloalkyl-(C2-C4)-alkenyloxy, (C4-C8)-cycloalkenyl-(C1-C4)-alkenyloxy, (C1-C6)-alkyl-(C3-C8)-cycloalkoxy, (C2-C6)-alkenyl-(C3-C8)-cycloalkoxy, (C2-C6)-alkynyl-(C3-C8)-cycloalkoxy, (C1-C6)-alkyl-(C4-C8)-cycloalkenyloxy, (C2-C6)-alkenyl-(C4-C8)-cycloalkenyloxy, (C1-C4)-alkoxy-(C1-C6)-alkoxy, (C1-C4)-alkoxy-(C2-C6)-alkenyloxy, carbamoyl, (C1-C6)-mono- or dialkylcarbamoyl, (C1-C6)-mono- or dihaloalkylcarbamoyl, (C3-C8)-mono- or dicycloalkylcarbamoyl, (C1-C6)-alkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C6)-alkanoyloxy, (C3-C8)-cycloalkanoyloxy, (C1-C6)-haloalkoxycarbonyl, (C1-C6)-haloalkanoyloxy, (C1-C6)-alkaneamido, (C1-C6)-haloalkaneamido, (C2-C6)-alkeneamido, (C3-C8)-cycloalkaneamido, (C3-C8)-cycloalkyl-(C1-C4)-alkaneamido, (C1-C6)-alkylthio, (C2-C6)-alkenylthio, (C2-C6)-alkynylthio, (C1-C6)-haloalkylthio, (C2-C6)-haloalkenylthio, (C2-C6)-haloalkynylthio, (C3-C8)-cycloalkylthio, (C4-C8)-cycloalkenylthio, (C3-C8)-halocycloalkylthio, (C4-C8)-halocycloalkenylthio, (C3-C8)-cycloalkyl-(C1-C4)-alkylthio, (C4-C8)-cycloalkenyl-(C1-C4)-alkylthio, (C3-C8)-cycloalkyl-(C2-C4)-alkenylthio, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylthio, (C1-C6)-alkyl-(C3-C8)-cycloalkylthio, (C2-C6)-alkenyl-(C3-C8)-cycloalkylthio, (C2-C6)-alkynyl-(C3-C8)-cycloalkylthio, (C1-C6)-alkyl-(C4-C8)-cycloalkenylthio, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylthio, (C1-C6)-alkylsulfinyl, (C2-C6)-alkenylsulfinyl, (C2-C6)-alkynylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C2-C6)-haloalkenylsulfinyl, (C2-C6)-haloalkynylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C4-C8)-cycloalkenylsulfinyl, (C3-C8)-halocycloalksulfinyl, (C4-C8)-halocycloalkenylsulfinyl, (C3-C8)-cycloalkyl-(C1-C4)-alkylsulfinyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkylsulfinyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenylsulfinyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylsulfinyl, (C1-C6)-alkyl-(C3-C8)-cycloalkylsulfinyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkylsulfinyl, (C2-C6)-alkynyl-(C3-C8)-cycloalkylsulfinyl, (C1-C6)-alkyl-(C4-C8)-cycloalkenylsulfinyl, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylsulfinyl, (C1-C6)-alkylsulfonyl, (C2-C6)-alkenylsulfonyl, (C2-C6)-alkynylsulfonyl, (C1-C6)-haloalkylsulfonyl, (C2-C6)-haloalkenylsulfonyl, (C2-C6)-haloalkynylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C4-C8)-cycloalkenylsulfonyl, (C3-C8)-halocycloalkylsulfonyl, (C4-C8)-halocycloalkenylsulfonyl, (C3-C8)-cycloalkyl-(C1-C4)-alkylsulfonyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkylsulfonyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenylsulfonyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylsulfonyl, (C1-C6)-alkyl-(C3-C8)-cycloalkylsulfonyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkylsulfonyl, (C2-C6)-alkynyl-(C3-C8)-cycloalkylsulfonyl, (C1-C6)-alkyl-(C4-C8)-cycloalkenylsulfonyl, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylsulfonyl, (C1-C6)-alkylamino, (C2-C6)-alkenylamino, (C2-C6)-alkynylamino, (C1-C6)-haloalkylamino, (C2-C6)-haloalkenylamino, (C2-C6)-haloalkynylamino, (C3-C8)-cycloalkylamino, (C4-C8)-cycloalkenylamino, (C3-C8)-halocycloalkamino, (C4-C8)-halocycloalkenylamino, (C3-C8)-cycloalkyl-(C1-C4)-alkylamino, (C4-C8)-cycloalkenyl-(C1-C4)-alkylamino, (C3-C8)-cycloalkyl-(C2-C4)-alkenylamino, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylamino, (C1-C6)-alkyl-(C3-C8)-cycloalkylamino, (C2-C6)-alkenyl-(C3-C8)-cycloalkylamino, (C2-C6)-alkynyl-(C3-C8)-cycloalkylamino, (C1-C6)-alkyl-(C4-C8)-cycloalkenylamino, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylamino, (C1-C6)-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, arylcarbamoyl, aroyl, aroyloxy, aryloxycarbonyl, aryl-(C1-C4)-alkoxy, aryl-(C2-C4)-alkenyloxy, aryl-(C1-C4)-alkylthio, aryl-(C2-C4)-alkenylthio, aryl-(C1-C4)-alkylamino, aryl-(C2-C4)-alkenylamino, aryl-(C1-C6)-dialkylsilyl, diaryl-(C1-C6)-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl,

[0118] of which the nineteen last-mentioned radicals are optionally substituted in their cyclic moiety by one or more substituents from the group

[0119] halogen, cyano, nitro, amino, hydroxyl, thio, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, (C1-C4)-alkylamino, (C1-C4)-haloalkylamino, formyl and (C1-C4)-alkanoyl;

[0120] aryl, which is optionally substituted by one or more radicals from the group

[0121] halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C1-C6)-haloalkyloxy, (C2-C6)-haloalkenyloxy, (C2-C6)-haloalkynyloxy, (C3-C8)-cycloalkoxy, (C4-C8)-cycloalkenyloxy, (C3-C8)-halocycloalkoxy, (C4-C8)-halocycloalkenyloxy, carbamoyl, (C1-C6)-mono- or dialkylcarbamoyl, (C1-C6)-alkoxycarbonyl, (C1-C6)-alkanoyloxy, (C1-C6)-mono- or dihaloalkylcarbamoyl, (C1-C6)-haloalkoxycarbonyl, (C1-C6)-haloalkanoyloxy, (C1-C6)-alkaneamido, (C1-C6)-haloalkaneamido, (C2-C6)-alkeneamido, (C1-C6)-alkylthio, (C2-C6)-alkenylthio, (C2-C6)-alkynylthio, (C1-C6)-haloalkylthio, (C2-C6)-haloalkenylthio, (C2-C6)-haloalkynylthio, (C3-C8)-cycloalkylthio, (C4-C8)-cycloalkenylthio, (C3-C8)-halocycloalkthio, (C3-C8)-halocycloalkenylthio, (C1-C6)-alkylsulfinyl, (C2-C6)-alkenylsulfinyl, (C2-C6)-alkynylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C2-C6)-haloalkenylsulfinyl, (C2-C6)-haloalkynylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C4-C8)-cycloalkenylsulfinyl, (C3-C8)-halocycloalksulfinyl, (C4-C8)-halocycloalkenylsulfinyl, (C1-C6)-alkylsulfonyl, (C2-C6)-alkenylsulfonyl, (C2-C6)-alkynylsulfonyl, (C1-C6)-haloalkylsulfonyl, (C2-C6)-haloalkenylsulfonyl, (C2-C6)-haloalkynylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C4-C8)-cycloalkenylsulfonyl, (C3-C8)-halocycloalksulfonyl, (C4-C8)-halocycloalkenylsulfonyl, (C1-C6)-alkylamino, (C2-C6)-alkenylamino, (C2-C6)-alkynylamino, (C1-C6)-haloalkylamino, (C2-C6)-haloalkenylamino, (C2-C6)-haloalkynylamino, (C3-C8)-cycloalkylamino, (C4-C8)-cycloalkenylamino, (C3-C8)-halocycloalkamino and (C4-C8)-halocycloalkenylamino,

[0122] —C(═W)R11, OR11 or NR112;

[0123] R9 is (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C3-C8)-cycloalkyl-(C1-C4)-alkyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenyl, where the nine last-mentioned radicals are optionally substituted by one or more radicals from the group

[0124] halogen, cyano, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6) alkynyloxy and (C1-C6)-haloalkyloxy;

[0125] R10is hydrogen,

[0126] (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C3-C8)-cycloalkyl-(C1-C4)-alkyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenyl, (C1-C6)-alkyl-(C3-C8)-cycloalkyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkyl, (C2-C6)-alkynyl-(C3-C8)-cycloalkyl, (C1-C6)-alkyl-(C4-C8)-cycloalkenyl, (C2-C6)-alkenyl-(C4-C8)-cycloalkenyl,

[0127] where the fourteen last-mentioned radicals are optionally substituted by one or more radicals from the group

[0128] halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C1-C6)-haloalkyloxy, (C2-C6)-haloalkenyloxy, (C2-C6)-haloalkynyloxy, (C3-C8)-cycloalkoxy, (C4-C8)-cycloalkenyloxy, (C3-C8)-halocycloalkoxy, (C4-C8)-halocycloalkenyloxy, (C3-C8)-cycloalkyl-(C1-C4)-alkoxy, (C4-C8)-cycloalkenyl-(C1-C4)-alkoxy, (C3-C8)-cycloalkyl-(C2-C4)-alkenyloxy, (C4-C8)-cycloalkenyl-(C1-C4)-alkenyloxy, (C1-C6)-alkyl-(C3-C8)-cycloalkoxy, (C2-C6)-alkenyl-(C3-C8)-cycloalkoxy, (C2-C6)-alkynyl-(C3-C8)-cycloalkoxy, (C1-C6)-alkyl-(C4-C8)-cycloalkenyloxy, (C2-C6)-alkenyl-(C4-C8)-cycloalkenyloxy, (C1-C4)-alkoxy-(C1-C6)-alkoxy, (C1-C4)-alkoxy-(C2-C6)-alkenyloxy, carbamoyl, (C1-C6)-mono- or dialkylcarbamoyl, (C1-C6)-mono- or dihaloalkylcarbamoyl, (C3-C8)-mono- or dicycloalkylcarbamoyl, (C1-C6)-alkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C6)-alkanoyloxy, (C3-C8)-cycloalkanoyloxy, (C1-C6)-haloalkoxycarbonyl, (C1C6)-haloalkanoyloxy, (C1C6)-alkaneamido, (C1-C6)-haloalkaneamido, (C2-C6)-alkeneamido, (C3-C8)-cycloalkaneamido, (C3-C8)-cycloalkyl-(C1-C4)-alkaneamido, (C1-C6)-alkylthio, (C2-C6)-alkenylthio, (C2-C6)-alkynylthio, (C1-C6)-haloalkylthio, (C2-C6)-haloalkenylthio, (C2-C6)-haloalkynylthio, (C3-C8)-cycloalkylthio, (C4-C8)-cycloalkenylthio, (C3-C8)-halocycloalkthio, (C4-C8)-halocycloalkenylthio, (C3-C8)-cycloalkyl-(C1-C4)-alkylthio, (C4-C8)-cycloalkenyl-(C1-C4)-alkylthio, (C3-C8)-cycloalkyl-(C2-C4)-alkenylthio, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylthio, (C1-C6)-alkyl-(C3-C8)-cycloalkylthio, (C2-C6)-alkenyl-(C3-C8)-cycloalkylthio, (C2-C6)-alkynyl-(C3-C8)-cycloalkylthio, (C1-C6)-alkyl-(C4-C8)-cycloalkenylthio, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylthio, (C1-C6)-alkylsulfinyl, (C2-C6)-alkenylsulfinyl, (C2-C6)-alkynylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C2-C6)-haloalkenylsulfinyl, (C2-C6)-haloalkynylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C4-C8)-cycloalkenylsulfinyl, (C3-C8)-halocycloalksulfinyl, (C4-C8)-halocycloalkenylsulfinyl, (C3-C8)-cycloalkyl-(C1-C4)-alkylsulfinyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkylsulfinyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenylsulfinyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylsulfinyl, (C1-C6)-alkyl-(C3-C8)-cycloalkylsulfinyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkylsulfinyl, (C2-C6)-alkynyl-(C3-C8)-cycloalkylsulfinyl, (C1-C6)-alkyl-(C4-C8)-cycloalkenylsulfinyl, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylsulfinyl, (C1-C6)-alkylsulfonyl, (C2-C6)-alkenylsulfonyl, (C2-C6)-alkynylsulfonyl, (C1-C6)-haloalkylsulfonyl, (C2-C6)-haloalkenylsulfonyl, (C2-C6)-haloalkynylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C4-C8)-cycloalkenylsulfonyl, (C3-C8)-halocycloalksulfonyl, (C4-C8)-halocycloalkenylsulfonyl, (C3-C8)-cycloalkyl-(C1-C4)-alkylsulfonyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkylsulfonyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenylsulfonyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylsulfonyl, (C1-C6)-alkyl-(C3-C8)-cycloalkylsulfonyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkylsulfonyl, (C2-C6)-alkynyl-(C3-C8)-cycloalkylsulfonyl, (C1-C6)-alkyl-(C4-C8)-cycloalkenylsulfonyl, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylsulfonyl, (C1-C6)-alkylamino, (C2-C6)-alkenylamino, (C2-C6)-alkynylamino, (C1-C6)-haloalkylamino, (C2-C6)-haloalkenylamino, (C2-C6)-haloalkynylamino, (C3-5-C8)-cycloalkylamino, (C4-C8)-cycloalkenylamino, (C3-C8)-halocycloalkamino, (C4-C8)-halocycloalkenylamino, (C3-C8)-cycloalkyl-(C1-C4)-alkylamino, (C4-C8)-cycloalkenyl-(C1-C4)-alkylamino, (C3-C8)-cycloalkyl-(C2-C4)-alkenylamino, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylamino, (C1-C6)-alkyl-(C3-C8)-cycloalkylamino, (C2-C6)-alkenyl-(C3-C8)-cycloalkylamino, (C2-C6)-alkynyl-(C3-C8)-cycloalkylamino, (C1-C6)-alkyl-(C4-C8)-cycloalkenylamino, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylamino, (C1-C6)-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, aryl-(C1-C4)-alkoxy, aryl-(C2-C4)-alkenyloxy, aryl-(C1-C4)-alkylthio, aryl-(C2-C4)-alkenylthio, aryl-(C1-C4)-alkylamino, aryl-(C2-C4)-alkenylamino, aryl-(C1-C6)-dialkylsilyl, diaryl-(C1-C6)-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

[0129] halogen, cyano, nitro, amino, hydroxyl, thio, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C3-C8)-cycloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, (C1-C4)-alkylamino, (C1-C4)-haloalkylamino, formyl and (C1-C4)-alkanoyl;

[0130] aryl, 5- or 6-membered heteroaromatic,

[0131] where the two last-mentioned radicals are optionally substituted by one or more radicals from the group

[0132] halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C1-C6)-haloalkyloxy, (C2-C6)-haloalkenyloxy, (C2-C6)-haloalkynyloxy, (C3-C8)-cycloalkoxy, (C4-C8)-cycloalkenyloxy, (C3-C8)-halocycloalkoxy, (C4-C8)-halocycloalkenyloxy, carbamoyl, (C1-C6)-mono- or dialkylcarbamoyl, (C1-C6)-alkoxycarbonyl, (C1-C6)-alkanoyloxy, (C1-C6)-mono- or dihaloalkylcarbamoyl, (C1-C6)-haloalkoxycarbonyl, (C1-C6)-haloalkanoyloxy, (C1-C6)-alkaneamido, (C1-C6)-haloalkaneamido, (C2-C6)-alkeneamido, (C1-C6)-alkylthio, (C2-C6)-alkenylthio, (C2-C6)-alkynylthio, (C1-C6)-haloalkylthio, (C2-C6)-haloalkenylthio, (C2-C6)-haloalkynylthio, (C3-C8)- cycloalkylthio, (C4-C8)-cycloalkenylthio, (C3-C8)-halocycloalkthio, (C4-C8)-halocycloalkenylthio, (C1-C6)-alkylsulfinyl, (C2-C6)-alkenylsulfinyl, (C2-C6)-alkynylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C2-C6)-haloalkenylsulfinyl, (C2-C6)-haloalkynylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C4-C8)-cycloalkenylsulfinyl, (C3-C8)-halocycloalksulfinyl, (C4-C8)-halocycloalkenylsulfinyl, (C1-C6)-alkylsulfonyl, (C2-C6)-alkenylsulfonyl, (C2-C6)-alkynylsulfonyl, (C1-C6)-haloalkylsulfonyl, (C2-C6)-haloalkenylsulfonyl, (C2-C6)-haloalkynylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C4-C8)-cycloalkenylsulfonyl, (C3-C8)-halocycloalksulfonyl, (C4-C8)-halocycloalkenylsulfonyl, (C1-C6)-alkylamino, (C2-C6)-alkenylamino, (C2-C6)-alkynylamino, (C1-C6)-haloalkylamino, (C2-C6)-haloalkenylamino, (C2-C6)-haloalkynylamino, (C3-C8)-cycloalkylamino, (C4-C8)-cycloalkenylamino, (C3-C8)-halocycloalkylamino and (C4-C8)-halocycloalkenylamino;

[0133] R11 is (C1-C10)-alkyl, haloalkyl, aryl,

[0134] which is optionally substituted by one or more radicals from the group

[0135] halogen, cyano, nitro, (C1C4)-alkoxy, (C1-C4)-alkyl, amino, (C1-C4)-monoalkylamino and (C1-C4)-dialkylamino;

[0136] NR102, OR10 or SR10.

[0137] The term “halogen” includes fluorine, chlorine, bromine and iodine.

[0138] The term “(C1-C4)-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 “(C1-C6)-alkyl” includes the abovementioned alkyl radicals, and, for example, the pentyl, 2-methylbutyl, 1,1-dimethylpropyl, hexyl radical. The term “(C1-C10)-alkyl” is to be understood as the abovementioned alkyl radicals, and, for example, the nonyl, 1-decyl or 2-decyl radical and the term “(C1-C20)-alkyl” is to be understood as the abovementioned alkyl radicals, and, for example, the undecyl, dodecyl, pentadecyl or eicosyl radical.

[0139] “(C1-C4)-Haloalkyl” is to be understood as an alkyl group mentioned under the term “(C1-C4)-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.

[0140] “(C1-C4)-Alkoxy” is to be understood as an alkoxy group whose hydrocarbon radical has the meaning given under the term “(C1-C4)-alkyl”. Alkoxy groups embracing a greater range of carbon atoms are to be understood correspondingly.

[0141] 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. “(C2-C4)-Alkenyl” is thus, for example, the vinyl, allyl, 2-methyl-2-propene or 2-butenyl group; “(C2-C6)-alkenyl” denotes the abovementioned radicals and, for example, the pentenyl, 2-methylpentenyl or the hexenyl group. The term “(C2-C20)-alkenyl” is to be understood as the abovementioned radicals and, for example, the 2-decenyl or the 2-eicosenyl group. “(C2-C4)-Alkynyl” is, for example, the ethynyl, propargyl, 2-methyl-2-propyne or 2-butynyl group. “(C2-C6)-Alkynyl” is to be understood as the abovementioned radicals and, for example, the 2-pentynyl- or the 2-hexynyl group and “(C2-C20)-alkynyl” is to be understood as the abovementioned radicals and, for example, the 2-octynyl or the 2-decynyl group.

[0142] “(C3-C8)—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.

[0143] The term “(C3-C8)-cycloalkyl-(C1-C4)-alkyl” is to be understood as, for example, the cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylbutyl radical, and the term “(C1-C6)-alkyl-(C3-C8)-cycloalkyl” is to be understood as, for example, the 1-methylcyclopropyl, 1-methylcyclopentyl, 1-methylcyclohexyl, 3-hexylcyclobutyl and 4-tert-butyl-cyclohexyl radical.

[0144] “(C1-C4)-Alkoxy-(C1-C6)-alkyloxy” is an alkoxy group as defined above which is substituted by a further alkoxy group, such as, for example, 1-ethoxyethoxy.

[0145] “(C3-C8)-Cycloalkoxy” or “(C3-C8)-cycloalkylthio” is to be understood as one of the abovementioned (C3-C8)-cycloalkyl radicals which is linked via an oxygen or sulfur atom.

[0146] “(C3-C8)-Cycloalkyl-(C1-C6)-alkoxy” is, for example, the cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclohexylethoxy or the cyclohexylbutoxy group;

[0147] The term “(C1-C4)-alkyl-(C3-C8)-cycloalkoxy” is, for example, the methylcyclopropyloxy, methylcyclobutyloxy or the butylcyclohexyloxy group.

[0148] “(C1-C6)-Alkylthio” is an alkylthio group whose hydrocarbon radical has the meaning given under the term “(C1-C6)-alkyl”.

[0149] Correspondingly, “(C1-C6)-alkylsulfinyl” is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfinyl group and “(C1-C6)-alkylsulfonyl” is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfonyl group.

[0150] “(C1-C6)-Alkylamino” is a nitrogen atom which is substituted by one or two identical or different alkyl radicals of the above definition.

[0151] The term “(C1-C6)-mono- or dialkylcarbamoyl” is a carbamoyl group having one or two hydrocarbon radicals which have the meaning given under the term “(C1-C6-alkyl)” and which, in the case of two hydrocarbon radicals, may be identical or different.

[0152] Correspondingly, “(C1-C6)-dihaloalkylcarbamoyl” is a carbamoyl group which carries two (C1-C6)-haloalkyl radicals in accordance with the above definition or one (C1-C6)-haloalkyl radical and one (C1-C6)-alkyl radical in accordance with the above definition.

[0153] “(C1-C6)-Alkanoyl” is, for example, the acetyl, propionyl, butyryl or 2-methylbutyryl group.

[0154] 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.

[0155] 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.

[0156] “Aryl-(C1-C4)-alkoxy” is an aryl radical which is attached via a (C1-C4)-alkoxy group, for example the benzyloxy, phenylethoxy, phenylbutoxy or naphthylmethoxy radical.

[0157] “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.

[0158] “Aryl-(C1-C4)-alkylthio” is an aryl radical which is attached via an alkylthio radical, for example the benzylthio, naphthylmethylthio or the phenylethylthio radical.

[0159] The term “(C1-C6)-trialkylsilyl” denotes a silicon atom which carries three identical or different alkyl radicals in accordance with the above definition. Correspondingly “aryl-(C1-C6)-dialkylsilyl” is a silicon atom which carries one aryl radical and two identical or different radicals in accordance with the above definition, “diaryl-(C1-C6)-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.

[0160] In cases where two or more radicals R10 are present in a substituent, such as, for example, in —C(═W)NR102, these radicals may be identical or different.

[0161] Preference is given to those compounds of the formula I in which

[0162] Y is C1-C6-alkyl which is mono- or polysubstituted by chlorine and/or fluorine;

[0163] m is zero;

[0164] Q is a 5-membered heterocyclic group

[0165] in which

[0166] a) X2=NRa and X3=CRbR1 or

[0167] b) X2=CRaR2 and X3=CRbR3 or

[0168] c) X2=CR4R5 and X3=CR6R7;

[0169] Ra and Rb together are a bond;

[0170] R1, R2, R3, R4 and R6 are each independently of one another hydrogen, halogen, C1-C2-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, C2-C8-alkynyl, where the four last-mentioned hydrocarbon radicals are optionally mono- or polysubstituted by identical or different radicals from a group A1 consisting of C1-C6-alkylcarbonyl, C1-C6-alkylaminocarbonyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylamino, Cl-C6-alkylcarbonylamino, C1-C6-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, C1-C3-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, C1-C3-alkyl and C1-C3-alkoxy, or are C1-C6-alkylcarbonyl, C1-C6-alkylaminocarbonyl, C1-C6-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 OR10, SR10 or N(R10)2;

[0171] R5 and R7 are each independently of one another hydrogen, halogen, C1-C12-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, C2-C8-alkynyl, where the four last-mentioned hydrocarbon radicals are optionally mono- or polysubstituted by identical or different radicals from a group A2 consisting of C1-C6-alkylcarbonyl, C1-C6-alkylaminocarbonyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylamino, C1-C6-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 C1-C6-alkylcarbonyl, C1-C6-alkylaminocarbonyl, C1-C6-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 OR10, SR10or N(R10)2;

[0172] R10 is hydrogen, benzyl, C1-C6-alkyl, C1-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl, C1-C6-alkylcarbonyl or C1-C6-alkylsulfonyl, where the eight last-mentioned radicals are optionally mono- or polysubstituted by identical or different halogen atoms.

[0173] Particular preference is given to compounds of the formula I in which

[0174] Y is trifluoromethyl;

[0175] R1, R2, R3, R4 and R6 are each independently of one another halogen, C1-C12-alkyl, C2-C12-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A3 consisting of C1-C4-alkylcarbonyl, C1-C4-alkylaminocarbonyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylamino, C1-C4-alkylcarbonylamino, C1-C4-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 OR10, SR10 or N(R10)2;

[0176] R5 and R7 are each independently of one another halogen, C1-C12-alkyl, C2-C12-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A4 consisting of C1-C4-alkylcarbonyl, C1-C4-alkylaminocarbonyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylamino, C1-C4-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 OR10, SR10 or N(R10)2;

[0177] R10 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl, C1-C4-alkylcarbonyl or C1-C4-alkylsulfonyl, where the six last-mentioned radicals are optionally mono- or polysubstituted by identical or different halogen atoms.

[0178] Very particular preference is given to compounds of the formula I in which

[0179] R1, R2, R3, R4 and R6 are each independently of one another C1-C10-alkyl, C2-C10-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A5 consisting of C1-C4-alkylcarbonyl, C1-C4-alkylaminocarbonyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylamino, C1-C4-alkylcarbonylamino, C1-C4-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 AS are each optionally mono- or polysubstituted by identical or different radicals from the group B2;

[0180] R5 and R7 are each independently of one another C1-C10-alkyl, C2-C10-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A6 consisting of C1-C4-alkylcarbonyl, C1-C4-alkylaminocarbonyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylamino, C1-C4-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.

[0181] 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 (C1-C4)-alkyl radicals and also mono-, di- and trialkanolamines of (C1-C4)-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 NaHSO4 and KHSO4. The salts which can be obtained in this manner likewise have insecticidal, acaricidal and nematicidal properties.

[0182] 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.

[0183] The present invention also provides processes for preparing compounds of the formula I:

[0184] To prepare compounds of the formula (I) in which

[0185] a) X1=W,X2=NRa, X3=CRbR1

[0186] and Ra, Rb and R1 are as defined above and W is oxygen, activated derivatives of the acid of the formula (II)

[0187] where X and Y are as defined above, are reacted in the presence of a base with a compound of the formula (III)

[0188] in which the radical R1 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.

[0189] 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):

[0190] 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.

[0191] 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.

[0192] 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).

[0193] 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).

[0194] 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 R1 is as defined above and R12 and R13 are each C1-C4-alkyl.

[0195] To prepare compounds of the formula (I) in which

[0196] b) X1=NRa, X2=CRR, X3=W

[0197] and Ra, Rb and R1 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.

[0198] To prepare compounds of the formula (I) in which

[0199] c) X1=V, X2=CRaR1, X3=NRb

[0200] and Ra, Rb and R1 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.

[0201] 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 R1 is as defined above, using an activating reagent, such as phosphorus oxychloride or phosphorus pentachloride.

[0202] It is also possible to react acid hydrazides of the formula (XI) with ortho esters of the formula (XII) where R1 is as defined above, and R12 is (C1-C4)-alkyl.

[0203] 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.

[0204] To prepare compounds of the formula (I) in which and Ra, Rb and R3 are as defined above and V is oxygen, compounds of the formula (XIV) are reacted with a dehydrating reagent.

[0205] 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).

[0206] 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.

[0207] 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)

[0208] 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.

[0209] To prepare compounds of the formula (I) in which

[0210] e) X1=V, X2=CR4R5, X3=CR6R7

[0211] and R4, R5, R6 and R7 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.

[0212] 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.

[0213] An acyl halide or an anhydride can be used as activated derivative of the acid.

[0214] 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).

[0215] 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).

[0216] 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).

[0217] For preparing compounds of the formula (I) in which

[0218] f) X1=NR , X2=CRbR1, X3=NR8

[0219] and Ra, Rb, R1 and R8 are as defined above, hydrazides of the formula (XX)

[0220] 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).

[0221] 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.

[0222] Once the group Q has been assembled, for example by condensation, cyclization or cycloaddition reactions, the radicals R1 to R9 may be derivatized further, if desired, employing the extensive arsenal of methods of organochemical synthesis.

[0223] 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.

[0224] 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 molluscs, 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:

[0225] From the order of the Acarina, for example, Acarus siro, Argas spp., Omithodoros 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.

[0226] From the order of the Isopoda, for example, Oniscus asselus, Armadium vulgar and Porcellio scaber.

[0227] From the order of the Diplopoda, for example, Blaniulus guttulatus.

[0228] From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spp.

[0229] From the order of the Symphyla, for example, Scutigerella immaculata.

[0230] From the order of the Thysanura, for example, Lepisma saccharina.

[0231] From the order of the Collembola, for example, Onychiurus armatus.

[0232] 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.

[0233] From the order of the Isoptera, for example, Reticulitermes spp.

[0234] From the order of the Anoplura, for example, Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.

[0235] From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea spp.

[0236] From the order of the Thysanoptera, for example, Hercinothrips femoralis, Thrips tabaci and Frankliniella spp.

[0237] From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.

[0238] 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, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.

[0239] 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, Tortrix viridana, Cuaphalocrocis spp. and Manduca spp.

[0240] 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.

[0241] From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

[0242] 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.

[0243] From the order of the Siphonaptera, for example, Xenopsylla cheopsis and Ceratophyllus spp.

[0244] From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans.

[0245] From the class of helminths, for example, Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis, as well as Fasciola.

[0246] From the class of Gastropoda, for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp. and Oncomelania spp.

[0247] From the class of Bivalva, for example, Dreissena spp.

[0248] 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).

[0249] 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.

[0250] 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.

[0251] 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:

[0252] 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.

[0253] 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.

[0254] 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.

[0255] 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.

[0256] 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.

[0257] 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.

[0258] 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.

[0259] 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.

[0260] 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.

[0261] 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.

[0262] The pest control agents include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds, substances produced by microorganisms and the like.

[0263] Preferred partners for the mixtures are

[0264] 1. from the group of phosphorus compounds

[0265] 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;

[0266] 2. from the group of carbamates

[0267] 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-5,1 1-dithia-9-dodecenoate (OK 135), 1-methylthio(ethylideneamino) N-methyl-N-(morpholinothio)carbamate (UC51717);

[0268] 3. from the group of carboxylic acid esters

[0269] 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 (1 RS)-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;

[0270] 4. from the group of amidines

[0271] amitraz, chlordimeform;

[0272] 5. from the group of tin compounds

[0273] cyhexatin, fenbutatin oxide;

[0274] 6. others

[0275] abamectin, Bacillus thuringiensis, bensultap, binapacryl, bromopropylate, buprofezin, camphechlor, cartap, chlorobenzilate, chlorfluazuron, 2-(4-chlorophenyl)-4,5-di-phenylthiophene (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-25 1-pentyl)diphenyl ether (MTI 800), granulosis and nuclear polyhedrosis viruses, fenthiocarb, flubenzimine, flucycloxuron, flufenoxuron, gamma-HCH, hexythiazox, hydramethylnon (AC217300), 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.

[0276] 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.

[0277] 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.

[0278] The active compounds are used in a customary manner appropriate for the use forms.

[0279] 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.

[0280] 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.

[0281] 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).

[0282] 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.

[0283] In a preferred embodiment, the invention provides 4-trifluoromethyl-3-oxadiazolyl, pyridine derivatives of the formula (I′),

[0284] where the symbols and indices are as defined below:

[0285] m is 0 or 1;

[0286] 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;

[0287] Y is —O—, —S—, —SO—, —SO2—, —O—CO—, —O—CO—, —SO2—O—, —O—SO2—, —NR1—, —NR2—CO—, —NR3—CO—O—, —NR1—CO—NR5—, —O—CO—CO—O—, —O—CO—NR6, —SO2—NR7 or —NR8—SO2—;

[0288] 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-C10)-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,

[0289] with the proviso, that the compounds in which

[0290] X=—, Y=O, R=H

[0291] X=—, Y=O, R=Me

[0292] X=—, Y=O, R=Et

[0293] X=—, Y=O, R=CHF2

[0294] X=—, Y=O, R=CH2Ph

[0295] X=CH2, Y=O, R=2-furanyl

[0296] X=CH2, Y=O, R=Me

[0297] X=CH2, Y=O, R=5-isoxazolyl

[0298] X=CH2, Y=O, R=5-nitrofuran-2-yl

[0299] X=CH2CH2,Y=O, R=H

[0300] X=CH2CH2; Y=O, R=Me

[0301] X=CH2CH2, Y=O,

[0302] X=CH2CH2, Y=O, R=Et

[0303] X=CH2CH2,Y=O, R=H

[0304] X=CH2CH2; Y=OC(O), R=4-F-phenyl

[0305] X=CH2CH2, Y=OC(O), R=2,6-difluorophenyl

[0306] X=CH2CH2, Y=OC(O), R=4-nitrophenyl

[0307] X=CH2CH2, Y=OC(O), R=t-Bu

[0308] X=CH2CH2, Y=OC(O), R=cyclopropyl

[0309] X=CH2CH2, Y=OC(O), R=Me

[0310] X=CH2CH2CH2, Y=O, R=H

[0311] X=—Y=S(O), R=4-bromobenzyl

[0312] X=CH2,Y=S,R=Me

[0313] X=CH2, Y=S(O), R=Me

[0314] X=CH2, Y=S(0)2, R=t-Bu

[0315] X=CH2, Y=S, R=2-thienyl

[0316] X=CH2CH2, Y=S, R=Me

[0317] X=CH2CH2, Y=S, R=n-Pr

[0318] X=CH2CH2, Y=S, R=benzyl

[0319] X=CH2CH2, Y=S, R=2-thienylmethyl

[0320] X=CH2CH2CH2, Y=S, R=Me x═CH2CH2CH2, Y=S(O), R=Me

[0321] X=CH2CH2CH2CH2, Y=S, R=CH2CH2CH2CH2OMe

[0322] are not included.

[0323] m is preferably 0.

[0324] If m is 1 and Y contains an S(O), group, n is preferably 2.

[0325] X is preferably a single bond, CH2, CH2—CH2, CH2—CH(CH3) or —CH2—C(CH3)2—.

[0326] Y is preferably —O—, —S—, —SO—, —SO2—, —O—CO—, —O—CO—O, —O—CO—NR6—, —SO—NR—, —O—SO2— or —SO2—O—.

[0327] R,R1,R2,R3 ,R ,R5,R6,R7,R8 are preferably identical or different and are independently of one another H, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C6-C8)-cycloalkynyl, heterocyclyl or -(CH2)1-4-heterocyclyl,

[0328] where the eight last-mentioned radicals are unsubstituted or substituted by one or more radicals from the group consisting of

[0329] halogen, cyano, citro, hydroxyl, —C(═W)R9, (═W), —C(═NOR9)R9, —C(═NNR92)R9, —C(═W)OR9, —C(═W)NR92, —OC(═W)R9, —OC(═W)OR9, —NR9C(═W)R9, —N[C(═W)R9]2, —NR9C(═W)OR9, —C(═W)NR9—NR92, —C(═W)NR9—NR9[C(═W)R9], —NR9—C(═W)NR92, —NR9—NR9C(═W)R?—NR9—N[C(═W)R9]2, —N[(C═W)R9]—NR92, —NR9—N[(C═W)R9]2, —NR9—NR9[(C═W)WR9], —NR9—[(C═W)NR92], —NR9(C═NR9)R9, —NR9(C═NR9)NR92, —O—NR92, —O—NR9(C═W)R9, —SO2NR92, —NR9SO2R9, —SO2OR9, —OSO2R9, —OR9, —NR92, —SR9, —SiR93, —SeR9, —PR92, —P(═W)R92, —SOR9, —SO2R9, —PW2R92, —PW3R92, aryl and heterocyclyl,

[0330] the two last-mentioned radicals of which are unsubstituted or substituted by one or more radicals from the group consisting of

[0331] (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C6-C8)-cycloalkynyl, (C1-C6)-haloalkyl, (C2-C6)-haloalkenyl, (C2-C6)-haloalkynyl, halogen, —OR10, —NR102, —SR10, —SiR103, —C(═W)R10, —C(═W)OR10, —C(═W)NR102, —SOR10, —SO2R10, nitro, cyano and hydroxyl,

[0332] and where optionally R and R1, R and R5, R and R6, R and R7 and R and R8 together are —(CH2)4—, —(CH2)5—, —(CH2)2—O—(CH2)2—, (CH2)2—NR—(CH2and where X and R together, if appropriate, may also form a ring system, 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.

[0333] Preferred to form the ring system are —(CH2)3—, —(CH2)4—, —(CH2)5—, —(CH2)2—O—(CH2)2—, —(CH2)2—NR3—(CH2)2—, —(thiophen-3,4-diyl)—C(O)—, CH(imidazolyl-)CF2C(O)—, —CH(Me)CH2C(O)—, —CMe2CH2C(O)—, —CH(Me)CH(Me)C(O)—, —CH2CH2CH2C(O)—, —CH(Me)CH2CH2C(O)—, —CH2CH(Me)CH2C(O)—, —CH2CMe2CH2C(O)—, —CH2C[—(CH2)4—]CH2C(O)—, —(1,2-cyclohexylene)—C(O)—, —(cyclohexene-4,5-diyl)—C(O)—, —CH2—C(H)Ph—CH2—C(O)—, —CMe═CMe—C(O)—, —CH2—CH2—C(O)—, especially preferred are —(CH2)3—, —(CH2)4—, —(CH2)5, —(CH2)2—O—(CH2)2—, —(CH2)2—NR3—(CH2)2—.

[0334] W is O or S.

[0335] R9 is hydrogen,

[0336] (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C3-C8)-cycloalkyl-(C1-C4)-alkyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenyl, (C1-C6)-alkyl-(C3-C8)-cycloalkyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkyl, (C2-C6)-alkynyl-(C3-C8)-cycloalkyl, (C1-C6)-alkyl-(C4-C8)-cycloalkenyl, (C2-C6)-alkenyl-(C4-C8)-cycloalkenyl,

[0337] where the fourteen last-mentioned radicals are unsubstituted or substituted by one or more radicals from the group consisting of

[0338] halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C1-C6)-haloalkyloxy, (C2-C6)-haloalkenyloxy, (C2-C6)-haloalkynyloxy, (C3-C8)-cycloalkoxy, (C4-C8)-cycloalkenyloxy, (C3-C8)-halocycloalkoxy, (C4-C8)-halocycloalkenyloxy, (C3-C8)-cycloalkyl-(C1-C4)-alkoxy, (C4-C8)-cycloalkenyl-(C1-C4)-alkoxy, (C3-C8)-cycloalkyl-(C2-C4)-alkenyloxy, (C4-C8)-cycloalkenyl-(C1-C4)-alkenyloxy, (C1-C6)-alkyl-(C3-C8)-cycloalkoxy, (C2-C6)-alkenyl-(C3-C8)-cycloalkoxy, (C2-C6) alkynyl-(C3-C8)-cycloalkoxy, (C1-C6)-alkyl-(C4-C8)-cycloalkenyloxy, (C2-C6)-alkenyl-(C4-C8)-cycloalkenyloxy, (C1-C4)-alkoxy-(C1-C6)-alkoxy, (C1-C4)-alkoxy-(C2-C6)-alkenyloxy, carbamoyl, (C1-C6)-mono- or -dialkylcarbamoyl, (C1-C6)-mono- or dihaloalkylcarbamoyl, (C3-C8)-mono- or dicycloalkylcarbamoyl, (C1-C6)-alkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C6)-alkanoyloxy, (C3-C8)-cycloalkanoyloxy, (C1-C6)-haloalkoxycarbonyl, (C1-C6)-haloalkanoyloxy, (C1-C6)-alkanamido, (C1-C6)-haloalkanamido, (C2-C6)-alkenamido, (C3-C8)-cycloalkanamido, (C3-C8)-cycloalkyl-(C1-C4)-alkanamido, (C1-C6)-alkylthio, (C2-C6)-alkenylthio, (C2-C6)-alkynylthio, (C1-C6)-haloalkylthio, (C2-C6)-haloalkenylthio, (C2-C6)-haloalkynylthio, (C3C8)-cycloalkylthio, (C4-C8)-cycloalkenylthio, (C3-C8)-halocycloalkylthio, (C4-C8)-halocycloalkenyllthio, (C3-C8)-cycloalkyl-(C1-C4)-alkylthio, (C4-C8)-cycloalkenyl-(C1-C4)-alkylthio, (C3-C8)-cycloalkyl -(C2-C4)-alkenylthio, (C4-C8)-cycloalkenyl-(C,—C4)-alkenylthio, (C1-C6)-alkyl-(C3-C8)-cycloalkylthio, (C2-C6)-alkenyl-(C3-C8)-cycloalkylthio, (C2-C6)-alkynyl-(C3-C8)-cycloalkylthio, (C1-C6)-alkyl-(C4-C8)-cycloalkenylthio, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylthio, (C1-C6)-alkylsulfinyl, (C2-C6)-alkenylsulfinyl, (C2-C6)-alkynylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C2-C6)-haloalkenylsulfinyl, (C2-C6)-haloalkynylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C4-C8)-cycloalkenylsulfinyl, (C3-C8)- halocycloalkylsulfinyl, (C4-C8)-halocycloalkenylsulfinyl, (C3-C8)-cycloalkyl-(C1-C4)-alkylsulfinyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkylsulfinyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenylsulfinyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylsulfinyl, (C1-C6)-alkyl-(C3-C8)-cyclo-alkylsulfinyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkylsulfinyl, (C2-C6)-alkynyl-(C3-C8)-cycloalkylsulfinyl, (C1-C6)-alkyl-(C4-C8)-cycloalkenylsulfinyl, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylsulfinyl, (C1-C6)-alkylsulfonyl, (C2-C6)-alkenylsulfonyl, (C2-C6)-alkynylsulfonyl, (C1-C6)-haloalkylsulfonyl, (C2-C6)-haloalkenylsulfonyl, (C2-C6)-haloalkynylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C4-C8)-cycloalkenylsulfonyl, (C3-C8)-halocycloalkylsulfonyl, (C4-C8)-halocycloalkenylsulfonyl, (C3-C8)-cycloalkyl-(C1-C4)-alkylsulfonyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkylsulfonyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenylsulfonyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylsulfonyl, (C1-C6)-alkyl-(C3-C8)-cycloalkylsulfonyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkylsulfonyl, (C2-C6)-alkynyl- (C3-C8)-cycloalkylsulfonyl, (C1-C6)-alkyl-(C4-C8)-cycloalkenylsulfonyl, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylsulfonyl, (C1-C6)-alkylamino, (C2-C6)-alkenylamino, (C2-C6)-alkynylamino, (C1-C6)-haloalkylamino, (C2-C6)-haloalkenylamino, (C2-C6)-haloalkynylamino, (C3-C8)-cycloalkylamino, (C4-C8)-cycloalkenylamino, (C3-C8)-halocycloalkylamino, (C4-C8)-halocycloalkenylamino, (C3-C8)-cycloalkyl-(C1-C4)-alkylamino, (C4-C8)-cycloalkenyl-(C1-C4)-alkylamino, (C3-C8)-cycloalkyl-(C2-C4)-alkenylamino, (C4-C8)-cycloalkenyl -(C1-C4)-alkenylamino, (C1-C6)-alkyl-(C3-C8)-cycloalkylamino, (C2-C6)-alkenyl-(C3-C8)-cycloalkylamino, (C2-C6)-alkynyl-(C3-C8)-cycloalkylamino, (C1-C6)-alkyl-(C4-C8)-cycloalkenylamino, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylamino, (C1-C6)-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, aryl-(C1-C4)-alkoxy, aryl-(C2-C4)-alkenyloxy, aryl-(C1-C4)-alkylthio, aryl-(C2-C4)-alkenylthio, aryl-(C1-C4)-alkylamino, aryl-(C2-C4)-alkenylamino, aryl-(C1-C6)-dialkylsilyl, diaryl-(C1-C6)-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl,

[0339] where the cyclic moiety of the fourteen last-mentioned radicals is unsubstituted or substituted by one or more radicals from the group consisting of

[0340] halogen, cyano, nitro, amino, hydroxyl, thio, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C3-C8)-cycloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, (C1-C4)-alkylamino, (C1-C4)-haloalkylamino, formyl and (C1-C4)-alkanoyl,

[0341] aryl, 4-, 5- or 6-membered heterocyclyl,

[0342] where the two last-mentioned radicals are unsubstituted or substituted by one or more radicals from the group consisting of

[0343] halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C1-C6)-haloalkyloxy, (C2-C6)-haloalkenyloxy, (C2-C6)-haloalkynyloxy, (C3-C8)-cycloalkoxy, (C4-C8)-cycloalkenyloxy, (C3-C8)-halocycloalkoxy, (C4-C8)-halocycloalkenyloxy, carbamoyl, (C1-C6)-mono- or -dialkylcarbamoyl, (C1-C6)-alkoxycarbonyl, (C1-C6)-alkanoyloxy, (C1-C6)-mono- or -dihaloalkylcarbamoyl, (C1-C6)-haloalkoxycarbonyl, (C1-C6)-haloalkanoyloxy, (C1-C6)-alkanamido, (C1-C6)-haloalkanamido, (C2-C6)-alkenamido, (C1-C6)-alkylthio, (C2-C6)-alkenylthio, (C2-C6)-alkynylthio, (C1-C6)-haloalkylthio, (C2-C6)-haloalkenylthio, (C2-C6)-haloalkynylthio, (C3-C8)-cycloalkylthio, (C4-C8)-cycloalkenylthio, (C3-C8)-halocycloalkylthio, (C4-C8)-halocycloalkenylthio, (C1-C6)-alkylsulfinyl, (C2-C6)-alkenylsulfinyl, (C2-C6)-alkynylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C2-C6)-haloalkenylsulfinyl, (C2-C6)-haloalkynylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C4-C8)-cycloalkenylsulfinyl, (C3-C8)- halocycloalkylsulfinyl, (C4-C8)-halocycloalkenylsulfinyl, (C1-C6)-alkylsulfonyl, (C2-C6)-alkenylsulfonyl, (C2-C6)-alkynylsulfonyl, (C1-C6)-haloalkylsulfonyl, (C2-C6)-haloalkenylsulfonyl, (C2-C6)-haloalkynylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C4-C8)-cycloalkenylsulfonyl, (C3-C8)-halocycloalkylsulfonyl, (C4-C8)-halocycloalkenylsulfonyl, (C1-C6)-alkylamino, (C2-C6)-alkenylamino, (C2-C6)-alkynylamino, (C1-C6)-haloalkylamino, (C2-C6)-haloalkenylamino, (C2-C6)-haloalkynylamino, (C3-C8)-cycloalkylamino, (C4-C8)-cycloalkenylamino, (C3-C8)-halocycloalkylamino and (C4-C8)-halocycloalkenylamino.

[0344] R and R1-R8 are particularly preferably H, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-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, SiMe3, —O—(C1-C6)-alkyl, —S—(C1-C6)-alkyl or —O—CO—(C1-C6)-alkyl.

[0345] Very particular preference is given to compounds of the formulae I′-1 to I′-32, also in the form of their pyridine N-oxides, where the symbols and indices are as defined above:

[0346] Preference is likewise given to the corresponding formulae I′-33 to I′-96 in which Y is —CH2CH2—, —CH2—CH(CH3)—, —CH2—CH2—CH2— and —CH2—C(CH3)2—.

[0347] The term “halogen” includes fluorine, chlorine, bromine and iodine.

[0348] The term “(C1-C4)-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 “(C1-C6)-alkyl” includes the abovementioned alkyl radicals, and, for example, the pentyl, 2-methylbutyl, 1,1-dimethylpropyl and hexyl radical. The term “(C1-C10)-alkyl” is to be understood as the abovementioned alkyl radicals, and, for example, the nonyl, 1-decyl or 2-decyl radical.

[0349] “(C1-C4)-Haloalkyl” is to be understood as an alkyl group mentioned under the term “(C1-C4)-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.

[0350] “(C1-C4)-Alkoxy” is to be understood as an alkoxy group whose hydrocarbon radical has the meaning given under the term “(C1-C4)-alkyl”. Alkoxy groups embracing a greater range of carbon atoms are to be understood correspondingly.

[0351] 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. “(C2-C4)-Alkenyl” is thus, for example, the vinyl, allyl, 2-methyl-2-propene or 2-butenyl group; “(C2-C6)-alkenyl” denotes the abovementioned radicals and, for example, the pentenyl, 2-methylpentenyl or the hexenyl group. “(C2-C4)-Alkynyl” is, for example, the ethynyl, propargyl, 2-methyl-2-propyne or 2-butynyl group. “(C2-C6)-Alkynyl” is to be understood as the abovementioned radicals and, for example, the 2-pentynyl or the 2-hexynyl group and “(C2-C10)-alkynyl” is to be understood as the abovementioned radicals and, for example, the 2-octynyl or the 2-decynyl group.

[0352] “(C3-C8)—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.

[0353] The term “(C3-C8)-cycloalkyl-(C1-C4)-alkyl” is to be understood as, for example, the cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylbutyl radical, and the term “(C1-C6)-alkyl-(C3-C8)-cycloalkyl” is to be understood as, for example, the 1-methylcyclopropyl, 1-methylcyclopentyl, 1-methylcyclohexyl, 3-hexyl-cyclobutyl and 4-tert-butyl-cyclohexyl radical.

[0354] “(C1-C4)-Alkoxy-(C1-C6)-alkyloxy” is an alkoxy group as defined above which is substituted by a further alkoxy group, such as, for example, 1-ethoxyethoxy.

[0355] “(C3-C8)—Cycloalkoxy” or “(C3-C8)-cycloalkylthio” is to be understood as one of the abovementioned (C3-C8)-cycloalkyl radicals which is linked via an oxygen or sulfur atom.

[0356] “(C3-C8)—Cycloalkyl-(C1-C6)-alkoxy” is, for example, the cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclohexylethoxy or the cyclohexylbutoxy group.

[0357] The term “(C1-C4)-alkyl-(C3-C8)-cycloalkoxy” is, for example, the methylcyclopropyloxy, methylcyclobutyloxy or the butylcyclohexyloxy group.

[0358] “(C1-C6)-Alkylthio” is an alkylthio group whose hydrocarbon radical has the meaning given under the term “(C1-C6)-alkyl”.

[0359] Correspondingly, “(C1-C6)-alkylsulfinyl” is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfinyl group and “(C1-C6)-alkylsulfonyl” is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfonyl group.

[0360] “(C1-C6)-Alkylamino” is a nitrogen atom which is substituted by one or two identical or different alkyl radicals of the above definition.

[0361] The term “(C1-C6)-mono- or -dialkylcarbamoyl” is a carbamoyl group having one or two hydrocarbon radicals which have the meaning given under the term “(C1-C6-alkyl)” and which, in the case of two hydrocarbon radicals, may be identical or different.

[0362] Correspondingly, “(C1-C6)-dihaloalkylcarbamoyl” is a carbamoyl group which carries two (C1-C6)-haloalkyl radicals in accordance with the above definition or one (C1-C6)-haloalkyl radical and one (C1-C6)-alkyl radical in accordance with the above definition.

[0363] “(C1-C6)-Alkanoyl” is, for example, the acetyl, propionyl, butyryl or 2-methylbutyryl group.

[0364] 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.

[0365] 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.

[0366] 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.

[0367] “Aryl-(C1-C4)-alkoxy” is an aryl radical which is attached via a (C1-C4)-alkoxy group, for example the benzyloxy, phenylethoxy, phenylbutoxy or naphthylmethoxy radical.

[0368] “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.

[0369] “Aryl-(C1-C4)-alkylthio” is an aryl radical which is attached via an alkylthio radical, for example the benzylthio, naphthylmethylthio or the phenylethylthio radical.

[0370] The term “(C1-C6)-trialkylsilyl” denotes a silicon atom which carries three identical or different alkyl radicals in accordance with the above definition. Correspondingly “aryl-(C1-C6)-dialkylsilyl” is a silicon atom which carries one aryl radical and two identical or different alkyl radicals in accordance with the above definition, “diaryl-(C1-C6)-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.

[0371] In cases where two or more radicals R9 are present in a substituent, such as, for example, in —C(═W)NR92, these radicals may be identical or different.

[0372] 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 (C1-C4)-alkyl radicals and also mono-, di- and trialkanolamines of (C1-C4)-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 NaHSO4 and KHS04. The salts which can be obtained in this manner likewise have insecticidal, acaricidal and nematicidal properties.

[0373] 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.

[0374] 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.

[0375] 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.

[0376] 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′).

[0377] For preparing compounds of the formula (I′), for example, activated derivatives of the acid of the formula (II′),

[0378] are reacted in the presence of a base with a compound of the formula (III′),

[0379] 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.

[0380] 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′):

[0381] 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).

[0382] 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.

[0383] 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).

[0384] 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.

[0385] Central intermediates of ethers, thioethers and analogous derivatives are haloalkyl- or hydroxyalkyl-substituted oxadiazole derivatives of the formula (V′),

[0386] which can then be converted into the corresponding target compounds using standard processes of organic synthesis.

[0387] 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, NaNH2, NaOH, KOH, Na2CO3. 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.

[0388] 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′=NH2).

[0389] The synthesis of the central intermediate ((V′); V′=NH2) 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′=NH2) is effected by the reaction with suitable electrophiles.

[0390] 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:

[0391] The synthesis is carried out by oxidation with an oxidizing agent, for example meta-chloroperbenzoic acid, with an appropriately selected stoichiometry and temperature.

[0392] 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.

[0393] Starting from the hydroxyalkyl oxadiazol ((V′); V′=OH) the respective sulfonates can be prepared analogously:

[0394] 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′).

[0395] 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.

[0396] 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 OberschleiBheim, 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.

[0397] 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.

[0398] 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.

[0399] 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.

[0400] 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′).

[0401] 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:

[0402] From the order of the Acarina, for example, Acarus siro, Argas spp., Omithodoros 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.

[0403] From the order of the Isopoda, for example, Oniscus asselus, Armadium vulgare and Porcellio scaber.

[0404] From the order of the Diplopoda, for example, Blaniulus guttulatus.

[0405] From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spp.

[0406] From the order of the Symphyla, for example, Scutigerella immaculata.

[0407] From the order of the Thysanura, for example, Lepisma saccharina.

[0408] From the order of the Collembola, for example, Onychiurus armatus.

[0409] 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.

[0410] From the order of the Isoptera, for example, Reticulitermes spp.

[0411] From the order of the Anoplura, for example, Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.

[0412] From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea spp.

[0413] From the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci.

[0414] From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.

[0415] 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 comi, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.

[0416] 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.

[0417] 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.

[0418] From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

[0419] 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.

[0420] From the order of the Siphonaptera, for example, Xenopsylla cheopsis and Ceratophyllus spp.

[0421] From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans.

[0422] From the class of helminths, for example, Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis, as well as Fasciola.

[0423] 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.

[0424] 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.

[0425] 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.

[0426] 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.

[0427] In general, the compositions according to the invention comprise from 1 to 95% by weight of the active compounds of the formula (I′).

[0428] For preparing the compositions according to the invention, the active compound and the other additives are combined and formulated as a suitable use form.

[0429] 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.

[0430] 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:

[0431] 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.

[0432] 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.

[0433] 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.

[0434] 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.

[0435] 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.

[0436] 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.

[0437] 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.

[0438] 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.

[0439] 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.

[0440] 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.

[0441] 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.

[0442] The pesticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds and substances produced by microorganisms.

[0443] Preferred partners for the mixtures are:

[0444] 1. from the group of phosphorus compounds

[0445] 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, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, sulprofos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, thiometon, triazophos, trichlorphon, vamidothion;

[0446] 2. from the group of carbamates

[0447] alanycarb (OK-135), aldicarb, 2-sec-butylphenyl methylcarbamate (BPMC), carbaryl, carbofuran, carbosulfan, cloethocarb, benfuracarb, 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 (UC51717), triazamate;

[0448] 3. from the group of carboxylic acid esters

[0449] acrinathrin, allethrin, alphametrin, 5-benzyl-3-furylmethyl (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-dimethylcyclo-propanecarboxylate (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-5 6701);

[0450] 4. from the group of amidines

[0451] amitraz, chlordimeform;

[0452] 5. from the group of tin compounds

[0453] cyhexatin, fenbutatin oxide;

[0454] 6. others

[0455] 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 (Rol 2-0470), 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 (AC217300), lufenuron, imidacloprid, indoxacarb (DPX-MP062), kanemite (AKD-2023), M-020, MTI-446, ivermectin, M-020, methoxyfenozide (Intrepid, RH-2485), milbemectin, NC-1 96, 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,

[0456] 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.

[0457] 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.

[0458] The active compounds are used in a customary manner appropriate for the use forms.

[0459] 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.

[0460] 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.

[0461] 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).

[0462] 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.

[0463] 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.

[0464] 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.

[0465] 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.

[0466] The invention therefore also provides the use of compounds of the formula (I′) for controlling harmful organisms in transgenic crop plants.

[0467] 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.

[0468] 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.

[0469] The examples below serve to illustrate the invention.

EXAMPLES

[0470] I. Compounds of Formula (I)

[0471] A. Formulation Examples

[0472] 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.

[0473] 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.

[0474] 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.

[0475] 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.

[0476] 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.

[0477] B. Chemical Examples

Example No. 1

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

[0478] 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.

[0479] 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.

[0480]

1
H-NMR (CDCl3, 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)

[0481] 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.

[0482]

1
H-NMR (CDCl3, 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)

[0483] 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.

[0484]

1
H-NMR (CDCl3, 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)

[0485] 500 mg of 4-trifluoromethylpyridine-3-thiocarboxamide and 440 mg of ethyl 4-chloroacetate were dissolved in 5 ml of dimethylformamide and heated at 1 00° 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 (MgSO4), filtered and concentrated and the residue was purified by chromatography. This gave the desired product in pure form as a colorless oil.

[0486]

1
H-NMR (CDCl3, 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)

[0487] 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.

[0488]

1
H-NMR (CDCl3, 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)

[0489] 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.

[0490]

1
H-NMR (CDCl3, 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)

[0491] 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 (Na2SO4), concentration and chromatographic purification gave 624 mg of the desired product as a slightly brown oil. 1H-NMR (CDCl3, 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)

[0492] 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.

[0493]

1
H-NMR (CDCl3, 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 9

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

[0494] Step 1: Tert-butyl 3-amino-3-(4-trifluoromethyl-3-pyridinecarbonyloxy-imino)propionate

[0495] 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.

[0496]

1
H-NMR (CDCl3, 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=5Hz, 1H), 9.13 (s, 1H) ppm.

[0497] Step 2: 3-(Tert-butoxycarbonylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0498] 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.

[0499]

1
H-NMR (CDCl3, 300MHz): d=1.5 (s, 9H), 3.88 (s, 2H), 7.79 (d, J=5 Hz, 1H), 9.02 (d, J=5Hz, 1H), 9.33 (s, 1H) ppm.

[0500] Step 3: 3-(Hydroxycarbonylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0501] 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.

[0502] Step 4: 3-(N-Isopropylcarbamoylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0503] 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.

[0504]

1
H-NMR (CDCl3, 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=5Hz, 1H), 9.37 (s, 1H) ppm.

Example No. 10

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

[0505] Step 1: Ethyl 2-amino-2-(4-trifluoromethyl-3-pyridinecarbonyloxyimino)acetate

[0506] 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.

[0507] Step 2: 3-Ethoxycarbonyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0508] 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.

[0509] Step 3: 5-(4-Trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxylic acid

[0510] 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 adjusted 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.

[0511] Step 4: N,N-Dimethyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxamide

[0512] 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.

[0513] 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

1TABLE 1

No.XYmWR1m.p. [° C.]1NCCl30OCH32NCCl30OCH2CH33NCCl30OCOOCH2CH34CHCCl30OCH35CHCCl30OCOOCH2CH36N(CF2)3CHCF20OCH37N(CF2)3CHCF20OCOOCH2CH38CH(CF2)3CHCF20OCH39CH(CF2)3CHCF20OCOOCH2CH310N(CF2)3CHCF20SCH2COOC(CH3)311N(CF2)3CHCF20SCH2CONHCH312CH(CF2)3CHCF20S(CH2)2CH313CH(CF2)3CHCF20SCOOCH2CH314N(CF2)2CHCF20OCH2CH315N(CF2)2CHCF20OCOOCH2CH316N(CF2)2CHCF20OOH17N(CF2)2CHCF20OOCH318CH(CF2)2CHCF20OCH319CH(CF2)2CHCF20OCOOCH2CH320CH(CF2)2CHCF20OOH21CH(CF2)2CHCF20ONHCH322NCF2CF30OCH323NCF2CF30OCH2CH324NCF2CF30O(CH2)2CH325NCF2CF30OCH(CH3)226NCF2CF30OCyclo-C6H1127NCF2CF30OCH2C═CH228NCF2CF30OCH2C≡CH29NCF2CF30OCH2CH2C≡CH30NCF2CF30OCH2C≡CCH2CH331NCF2CF30O(CH2)4C≡CH32NCF2CF30OCHFCF333NCF2CF30OCOOCH2CH334NCF2CF30OCH2COOC(CH3)335NCF2CF30OCH2CONHCH336NCF2CF30ONH237NCF2CF30ONHCH2CH338CHCF2CF30OCH339CHCF2CF30OCH2CH340CHCF2CF30O(CH2)2CH341CHCF2CF30OCH(CH3)242CHCF2CF30OCyclo-C6H1143CHCF2CF30OCH2C═CH244CHCF2CF30OCH2COOC(CH3)345CHCF2CF30ONH246CHCF2CF30ONHCOCH347CHCF2CF30ONHCOCH2CH348NCF2CF30SCH349NCF2CF30SCH2CH350NCF2CF30S(CH2)2CH351NCF2Cl0OCH352NCF2Cl0OCH2CH353NCF2Cl0O(CH2)2CH354NCF2Cl0OCH(CH3)255NCF2Cl0OCH2COOC(CH3)356NCF2Cl0OCH2CONHCH357NCF2Cl0OOH58NCF2Cl0OOCH359NCF2Cl0OOCH2CH360NCF2Cl0ONHCH361CHCF2Cl0OCH362CHCF2Cl0OCH2CH363CHCF2Cl0O(CH2)2CH364CHCF2Cl0OCH(CH3)265CHCF2Cl0OCH2COOC(CH3)366CHCF2Cl0OCH2CONHCH367CHCF2Cl0OOH68CHCF2Cl0OOCH369CHCF2Cl0OOCH2CH370CHCF2Cl0ONHCH371CHCF2Cl0OCyclo-C6H1172CHCF2Cl0OCH2C═CH273CHCF2Cl0OCOOCH2CH374CHCF2Cl0OCH2COOC(CH3)375CHCF2Cl0OCH2CONHCH376CHCF2Cl0OOCH377CHCF2Cl0ONHCH378CHCF30OCH3oil79CHCF30OCH2CH3oil80CHCF30O(CH2)2CH3oil81CHCF30OCH(CH3)2oil82CHCF30OCyclo-C3H5oil83CHCF30O(CH2)3CH3oil84CHCF30OCH(CH3)CH2CH3oil85CHCF30OCH2CH(CH3)2oil86CHCF30OC(CH3)3oil87CHCF30OCyclo-C4H788CHCF30O(CH2)4CH3oil89CHCF30OCH(CH3)(CH2)2CH390CHCF30O(CH2)2CH(CH3)291CHCF30OCH2C(CH3)392CHCF30OCyclo-C5H9oil93CHCF30O(CH2)5CH394CHCF30OC(CH2CH3)2CH395CHCF30OCyclo-C6H1196CHCF30O(CH2)6CH397CHCF30OCH(CH3)(CH2)4CH398CHCF30OCyclo-C7H1399CHCF30OCH2-cyclo-C6H11100CHCF30O2-Norbornyl101CHCF30O(CH2)7CH3102CHCF30OCH(CH2CH3)(CH2)5CH3103CHCF30O(CH2)8CH3104CHCF30O(CH2)3-cyclo-C6H11105CHCF30O(CH2)9CH3106CHCF30O1-Adamantyl107CHCF30O(CH2)10CH3108CHCF30O(CH2)11CH3109CHCF30OCH(CH3)(CH2)9CH3110CHCF30O(CH2)12CH3111CHCF30O(CH2)13CH3112CHCF30O(CH2)14CH3113CHCF30O(CH2)15CH3114CHCF30O(CH2)17CH3115CHCF30O(CH2)19CH3116CHCF30OCHO117CHCF30OCH═CH2oil118CHCF30OCH2C═C(CH3)2119CHCF30OCH2CH2C═CH2120CHCF30OCH2C═CH2121CHCF30OC(CH3)═CH2122CHCF30O(E)-CH2CH═CHCH2CH3123CHCF30O(Z)-CH2CH═CHCH2CH3124CHCF30O(CH2)5C═CH2125CHCF30OC(═CHCH3)CH362-64126CHCF30OGeranyl127CHCF30O3-Menthyl128CHCF30OC≡CH129CHCF30OCH2C≡CH130CHCF30OCH2CH2C≡CH131CHCF30OCH2CH2C≡CH132CHCF30O(CH2)4C≡CH133CHCF30OCHFCF3oil134CHCF30OCOOCH2CH3oil135CHCF30OCH2CH2OHoil136CHCF30OCH2CH2OCH3oil137CHCF30OCH2COOC(CH3)3oil138CHCF30OCH2SC6H5oil139CHCF30OCH2CONHCH3109-111140CHCF30OCH2CH(OH)CH2OH141CHCF30OCH2COCH3142CHCF30OCOCH3143CHCF30OCH2OC6H5144CHCF30OCOC6H5145CHCF30OCO(4-Cl)-C6H4146CHCF30OCF2CH3147CHCF30OCH2CN148CHCF30OCH2CH2CN149CHCF30OCH2CH(—O—)CH2150CHCF30OCH2(4-OCH3)C6H5151CHCF30OCH2-cyclo-(4-Oxo)-C6H8152CHCF30OCH2CH(OH)CH2SC6H5153CHCF30OCH2CH2Si(CH3)3154CHCF30OCH═CF2155CHCF30OCCl═CHCl156CHCF30O2-Pyridyl 99-101157CHCF30O2-Furyl158CHCF30O2-Thienyl106-108159CHCF30OCH2C≡CCH2CH2OTHP160CHCF30OCH2CH2CIoil161CHCF30OSi(CH3)3162CHCF30OOC6H5163CHCF30OOH164CHCF30OOCH3165CHCF30OOCH2CH3166CHCF30OOCHF2167CHCF30OOCH2C6H5168CHCF30OCH2SCH348-49169CHCF30OSC6H5170CHCF30OSeC6H5171CHCF30ONH2116-118172CHCF30ONHCH3173CHCF30ONHCH2CH3174CHCF30ON(CH2CH3)2175CHCF30OCONHCH2C═CH2105-107176CHCF30OCl177CHCF30OBr178CHCF30OCONH2206-208179CHCF30ONHCOCH3129-131180CHCF30ONHCOCH2CH3181CHCF30OOSO2CH3182CHCF30OSOCH2(4-Br)-C6H4183CHCF30ON(CH3)COOCH2C6H5184CHCF30ONHNH2185CHCF30ONHN(CH3)2186NCF30OCH3187NCF30OCH2CH3oil188NCF30O(CH2)2CH3oil189NCF30OCH(CH3)2oil190NCF30O(CH2)3CH3oil191NCF30OCH2CH(CH3)2oil192NCF30OC(CH3)3193NCF30O(CH2)4CH3oil194NCF30OCH(CH3)(CH2)2CH3195NCF30OCH2C(CH3)3196NCF30OCyclo-C5H9197NCF30O(CH2)5CH3198NCF30OCyclo-C6H11199NCF30OCH(CH3)(CH2)4CH3200NCF30OCH2-cyclo-C6H11201NCF30O(CH2)7CH3202NCF30O(CH2)8CH3203NCF30O(CH2)9CH3204NCF30OCH(CH3)(CH2)9CH3205NCF30O(CH2)15CH3206NCF30O(CH2)17CH3207NCF30O(CH2)19CH3208NCF30OCH2CH═C(CH3)2209NCF30OCH2CH2CH═CH2210NCF30OCH2CH═CH2211NCF30O(Z)-CH2CH═CHCH2CH3212NCF30O(CH2)5CH═CH2213NCF30OCH2C≡CH214NCF30OCH2C≡CCH2CH3215NCF30OCHFCF3216NCF30OCOOCH2CH3217NCF30OCH2CH2OH218NCF30OCH2CH2OCH3219NCF30OCH2COOC(CH3)3220NCF30OCH2SC6H5221NCF30OCH2CONHCH3222NCF30OCH2CH(OH)CH2OH223NCF30OCHO224NCF30OCOCH3225NCF30OCH2OC6H5226NCF30OCOC6H5227NCF30OCF2CH3228NCF30OCH2CN229NCF30OCH2CH2CN230NCF30OCH═CF2231NCF30O2-Furyl232NCF30OCH2C≡C—I233NCF30OOH234NCF30OOCH3235NCF30OOCH2CH3236NCF30OOCHF2237NCF30OOCH2C6H5238NCF30OSC6H5239NCF30ONH2240NCF30ONHCH3241NCF30ONHCH2CH3242NCF30ON(CH2CH3)2243NCF30ON(CH2CN)2244NCF30ON(CH3)2245NCF30ONHCOCH3246NCF30ONHCOCH2CH3247NCF30OOSO2CH3248NCF30ONHNH2249CHCF30SCH3250CHCF30SCH2CH3251CHCF30S(CH2)2CH3252CHCF30SCHO253CHCF30SCHFCF3254CHCF30SCH2C≡CH255CHCF30SCOOCH2CH3256CHCF30SCH2COOC(CH3)3257CHCF30SCH2CN258CHCF30SSeC6H5259NCF30SCH3260NCF30SCH2CH3261NCF30S(CH2)2CH3262NCF30SCHFCF3263NCF30SCH2CH2OH264NCF30SCH2COOC(CH3)3265CHCH2CH2Cl0OCH3266CHCH2CH2Cl0OCH2CH3267CHCH2CH2Cl0O(CH2)2CH3268CHCH2CH2Cl0OCH(CH3)2269CHCH2CH2Cl0OCH2SC6H5270CHCH2CH2Cl0OCH2CONHCH3271CHCH2CH2Cl0ONH2272CHCH2CH2Cl0ONHCH2CH3273NCH2CH2Cl0OCH2CH3274NCH2CH2Cl0ONH2275NCH2Cl0OCH3276CHCH2Cl0OCH3277CHCHF20OCH3278CHCHF20OCH2CH3279CHCHF20O(CH2)2CH3280CHCHF20OCH2CH═CH2281CHCHF20OC(CH3)═CH2282CHCHF20OCOOCH2CH3283CHCHF20OCH2CONHCH3284CHCHF20OCF2CH3285CHCHF20OCHO286CHCHF20ONH2287CHCHF20OCl288CHCHF20ONHCOCH3289CHCHF20ONHNH2290NCHF20OCH3291NCHF20OCH2CH3292NCHF20OCH(CH3)(CH2)4CH3293NCHF20OCH2CH═CH2294NCHF20OCOOCH2CH3295NCHF20ONH2296CHCF31OCH3297CHCF31OCOOCH2CH3298CHCF31OCH2COOC(CH3)3299CHCF31OCHFCF3300NCF30OCH2NHSO2CH3301NCF30O(CH2)2NHSO2CH3302NCF30OCH2NHSO2CH2CH3303NCF30OCH2NHSO2CH2C6H5304CHCF30O(CH2)4NHSO2CF3305CHCF30O(CH2)2S(CH2)2CH3306CHCF30O(CH2)4S(CH2)4OCH3307CHCF30S(CH2)2S(CH2)2CN308CHCF30SCH2NHSO2CH2CH3309CHCF30SCH2NHSO2CH2C6H5310CHCF30S(CH2)2NHSO2CH3311CHCF30SCH2NHSO2CH3312CHCF30SCH(CH3)CH2NHC6H5313CHCF30S(CH2)2S(2-F)-C6H4314CHCF30S(CH2)6NHCH2)6OCH3315CHCF30S(CH2)2NH-(2-F)-C6H4316CHCF30S(CH2)3NHCH2CN317CHCF30S(CH2)2O(3-Cl)-C6H4318CHCF30S(CH2)6NHCH2CF3319CHCF30S(CH2)2O(3-CH3)-C6H4320CHCF30OCH2NHC6H5321CHCF30O(CH2)4S(2-Br)-C6H4322CHCF30O(CH2)6NH(CH2)2OCH3323CHCF30O(CH2)2NH(CH2)4OCH3324CHCF30O(CH2)3NH-(4-CN)-C6H4325CHCF30O(CH2)2O(3-CH3)-C6H4326CHCF30O(CH2)4NHCH2CF3327CHCF30O(CH2)4NHCH2CN328CHCF30O(CH2)3O(4-OCH3)-C6H4329CHCF30OCH2SO2-tert-C4H9oil330CHCF30OCH2SO2-(4-F)-C6H4oil331CHCF30OCH2SO2-C6H5oil332CHCF30OCH2SOCH363333CHCF30OCH2SO—C6H5oil334CHCF30OCH2CONH(CH2)2CH380-82335CHCF30O(4-OCF3)—C6H457-59336CHCF30OCH2OCH3oil337CHCF30O

53-54338CHCF30O

oil339CHCF30OCH2CH2OCH2CH3oil340CHCF30OCH2CH2NC6H580-83341CHCF30O

80-81342CHCF30O

110-111343CHCF30OCH2CH2O(CO)-(4-Cl)-C6H480-82344CHCF30OCH2-(4-OCH3)-C6H454-55345CHCF30OCH2-(3-Cl)-C6H451-52346CHCF30OCH2-cyclo-C3H5oil347CHCF30OCH2-(4-C6H5)-C6H4oil348CHCF30O

143-144349CHCF30OCH2CH2O(CO)-(2,6-F2)-C6H357-58350CHCF30OCH2CH2O(CO)-(4-NO2)-C6H480-81351CHCF30OCH2-(2,6-Cl2)-C6H391-92352CHCF30OCH2CH2OSO2CH3oil353CHCF30OCH2CH2O(CO)-tert-C4H9oil354CHCF30OCH2-(3-F)-C6H450-51355CHCF30OCH2CONCH2C≡CH129-131356CHCF30OCH2CH2O(CO)-cyclo-C3H7oil357CHCF30OCH2CH2O(CO)CH3oil358CHCF30OCH2-[2,4-(CH3)2]—C6H385-86359CHCF30OCH2CONCH2CH═CH2210-212360CHCF30OCH2CON(CH2CH3)2oil361CHCF30OCH2CON(CH2)3CH377-79362CHCF30OCH2CONCH2-(2-furyl)139-141363CHCF30OCH2CONCH(CH3)2112-114364CHCF30OCH2CONCH(CH3)[(CH2)4CH3]73-75365CHCF30OCH2CONCH2CH2C6H5120-122366CHCF30OCH2CONCH2CH2OCH2CH378367CHCF30OCH2CONCH2CF3176-178368CHCF30OCH2CONCH(CH3)[(CH2)5CH3]85-86369CHCF30O

oil370CHCF30O

oil371CHCF30OCH2CH2-(1-pyrryl)oil372CHCF30OCH2CH2C6H5oil373CHCF30OCH2Cl53-54374CHCF30O(CH2)3OH38-39375CHCF30OCH2CONCH(CH3)[(CH2)2]CH368-69376CHCF30OCH2CH(OCH3)2oil377CHCF30OCH2CONCH2C(CH3)3oil378CHCF30OCH2CONC(CH3)2(CH2CH3)oil379CHCF30OCH2CONCH2CH2-cyclo-C6H1182-85380CHCF30OCH2CONCH(CH3)(1-naphthyl)142-146381CHCF30O(CH2)3Cloil382CHCF30OCH2CON-tert-C4H9oil383CHCF30OCH2CON(iso-C3H7)270-72384CHCF30OCH2CON(CH2)7CH379-81385CHCF30OCH2CON-cyclo-C6H11119-121386CHCF30OCH2CONCH2CH2-(4-Cl)-C6H4120-121387CHCF30OCH2CONCH2-(2-thienyl)137-139388CHCF30O

151-153389CHCF30OCH2CONHCH(CH3)(CH2CH3)87-89390CHCF30O(CH2)3SCH3oil391CHCF30O(CH2)3SOCH3oil392CHCF30OCH2CONC(CH3)2(C≡CH)111-113393CHCF30OCH2CONCH(CH3)CH2CH2CH(CH3)272-74394CHCF30O

oil395CHCF30OCH2CON-cyclo-C5H9110-112396CHCF30OCH2CON(CH2)4CH375-77397CHCF30O

190-192398CHCF30OCH2CON(3-CF3)C6H4136-138399CHCF30OCH2CON-cyclo-C8H17115-117400CHCF30O

oil401CHCF30OCH2CON-Adamantyloil402CHCF30OCH2CON(CH2CH2CH3)2oil403CHCF30OCH2CONCH(CH3)[(4-F)-C6H4]111-113404CHCF30OCH2CONCH2CH(CH3)291-93405CHCF30O

Oil406CHCF30OCH2CONCH2CH2OC6H5 99-101407CHCF30OCH2CH═NOCH3oil408CHCF30OCH2CONCH2CH2-[3,4-(OCH3)2]C6H3123-125409CHCF30OCH2CON-(2-Cl)C6H4138-140410CHCF30OCH2CON-(2-SCH3)C6H4136-138411CHCF30O

222-225412CHCF30O

207-209413CHCF30OCH2CON-(3-Br)C6H4129-131414CHCF30OCH2CON—N-(2,4,6-Cl3)C6H2153-155415CHCF30OCH2CON-(4-I)C6H4143-145416CHCF30OCH2CON—NCOCH2(3-Thienyl)185-187417CHCF30OCH2CH2CHOoil418CHCF30OCH2CON(CH3)[(CH2)3CH3]oil419CHCF30OCH2CON-(3,5-Cl2-2,4-F2)C6H166-167420CHCF30OCH2CON—C6H5215-217421CHCF30OCH2CON(CH3)(C6H11)oil422CHCF30OCH2CON(CH2CH3)(CH2CH═CH2)oil423CHCF30OCH2CON(CH2CH3)[CH(CH3)2]oil424CHCF30OCH2CONCH(CH3)[(CH3)2]108-110425CHCF30OCH2CON(CH2CH3)[CH2C(═CH2)(CH3)]oil426CHCF30OCH2CONCH2(4-tert-C4H9)C6H4oil427CHCF30OCH2CONCH(CH3)(tert-C4H9)oil428CHCF30OCH2CONCH(CH3)[CH2CH(CH3)(CH2CH3)]oil429CHCF30OCH2CONCH2COOCH2CH3103-105430CHCF30OCH2CON[(CH2)2CH3](CH2-cyclo-C3H7)oil431CHCF30OCH2CONCH(CH3)CH2CH2CH(CH3)280-82432CHCF30OCH2CONCH(CH2CH3)[CH2CH(CH3)2]oil433CHCF30OCH2C═O-(1-Piperidinyl)oil434CHCF30O

180-182435CHCF30OCH2CONCH2C(═CH2)(CH3)86-87436CHCF30OCH2CONCH[CH(CH3)2](COOCH3)oil437CHCF30OCH2CONCH2-cyclo-C3H7oil438CHCF30OCH2CON(CH2)5OHoil439CHCF30OCH2CON(CH3)(CH2CO2CH3)oil440CHCF30OCH2CON(CH3)(CH2CN)oil441CHCF30OCH2CONCH[CH2CH(CH3)2](CO2CH3)oil442CHCF30OCH2CON-(1-Piperidinyl)oil443CHCF30OCH2CONCH2CH2OCH397-99444CHCF30OCH2CH2SC6H5oil445CHCF30OCH2CH2SCH3oil446CHCF30OCH2CH2SCH2C6H5oil447CHCF30O

oil448CHCF30OCH2CON-(2-OH)C6H4162-164449CHCF30OCH2CON-(3-OH)C6H4oil450CHCF30OCH2CON-(2-CH3)C6H4163-164451CHCF30OCH2CON-(3-NO2)C6H4176-178452CHCF30OCH2CON-(3-OCF2CHFCl)C6H4120-121453CHCF30OCH2CON-(3-CF3-4-F)C6H3168-170454CHCF30OCH2CON-(2,4-Cl2)C6H3120-122455CHCF30OCH2CON-(2-F-4.Cl)C6H3148-151456CHCF30OCH2CON-[2,4-(CH3)2]C6H3123-125457CHCF30OCH2CON-[2,3-(CH3)2]C6H3waxy458CHCF30O

waxy459CHCF30OCH2CON-(2-CH3-3-Cl)C6H3160-162460CHCF30OCH2CON(CH2CH3)(C6H5)oil461CHCF30O

124-126462CHCF30OCH2CON(2-OCH3-5-Ph)C6H3167-169463CHCF30O

157-158464CHCF30OCH2CON-(3-NO2-4-Cl)C6H3oil465CHCF30OCH2CON-(2-Cl-4-CH3)C6H3106-108466CHCF30OCH2CON-(3-OCH2CH3)C6H4waxy467CHCF30O

169-171468CHCF30OCH2CON-(4-CH3)C6H4139-141469CHCF30OCH2CON-(1-Naphthyl)155-157470CHCF30OCH2CON-(3-I)C6H4135-137471CHCF30OCH2CON-(2-OCH2CH3)C6H4138472CHCF30OCH2CON-(2-OCH3)C6H4130-132473CHCF30OCH2CON-[3,5-(OCH3)2]C6H3130-132474CHCF30OCH2CON-(4-Cl)C6H4139-141475CHCF30OCH2CON-(3-CH3)C6H4oil476CHCF30OCH2CON-(3-OCH3)C6H4oil477CHCF30OCH2CON-(4-CH2CH3)C6H4122-123478CHCF30OCH2CON-(4-CF3)C6H4151-152479CHCF30OCH2CON-(2-CH3-4-Cl)C6H3165-167480CHCF30OCH2CH2NCH2C6H5oil481CHCF30OCH2CH2NCH2-(3-Pyridyl)oil482CHCF30OCH2CH═NOCH2CH3oil483CHCF30OCH2CH═NOC6H5oil484CHCF30OCH2CON-(4-NO2)C6H4181-183485CHCF30OCH2CON-(2-CH3-4-NO2)C6H3129-131486CHCF30OCH2CON-(2-Cl-3-CF3)C6H3136487CHCF30OCH2CON-(2-CN-4-Cl)C6H3157-159488CHCF30OCH2CON-(3,5-Cl2)C6H3167-169489CHCF30OCH2CON-(3,5-Cl2-4-OCF2CHF2)C6H2132-134490CHCF30OCH2CON-(2,4,5-Cl3)C6H2146491CHCF30OCH2CON-(3,5-Cl2-4-OCF2CHFCF3)C6H2124-126492CHCF30OCH2CON-(2-CF3-4-Cl)C6H3136493CHCF30O

oil494CHCF30O

91-93495CHCF30O

123-125496CHCF30O

81-83497CHCF30O

113-115498CHCF30OCOOH155-157499CHCF30O4-F-C6H4104-106500CHCF30OCON(C2H5)2oil501CHCF30OCONCH(CH3)2oil502CHCF30OCON(CH3)252-54503CHCF30OCONHCH2CCH105-107504CHCF30OCONH-cyclo-C3H5101-103505CHCF30OCONH2206-208506CHCF30O

72-74507CHCF30O

98-100508CHCF30O

108-110509CHCF30O

140-142510CHCF30OCONHCH3127-129511CHCF30OCONHCH2CH═CH2oil512CHCF30OCON(CH2CN)290-92513CHCF30O4-(t-C4H9)—C6H464-66514CHCF30O4-CF3—C6H489-91515CHCF30O4-CH3-3-F—C6H3104-106516CHCF30O2,4-di-Cl—C6H370-72517CHCF30O4-(NHSO2CH3)—C6H4204-206518CHCF30O2,6-di-Cl-C6H3139-141519CHCF30OCOOCH2C6H583-85520CHCF30OCONHC3H7oil521CHCF30O3,5-di-Br-4-(OCH3)—C6H2132-134522CHCF30OCHCl2oil523CHCF30OCCl3oil524CHCF30OCH(OCH3)2oil525CHCF30O3-CF3-C6H457-59526CHCF30OCON(CH2)5oil527CHCF30OCON(CH3)CH2C6H5oil528CHCF30OCONHCH2C6H596-98529CHCF30O

oil530CHCF30OCONH-n-C6H13oil531CHCF30OCON(CH2CH3)CH2C6H5oil532CHCF30OCONH-c-C6H11115-117533CHCF30OCON(n-C4H9)2oil534CHCF30O

oil535CHCF30OCONH-i-C4H9oil536CHCF30O

oil537CHCF30OCON(CH2)468-70538CHCF30OCON(CH3)-n-C6H13oil539CHCF30O

oil540CHCF30OCON(CH3)CH2CH3oil541CHCF30OCONHOCH3oil542CHCF30O

oil543CHCF30OCON(CH3)CH2CH2CH3oil544CHCF30OCONHCH2CH(OCH3)2oil545CHCF30OCONH-t-C4H9113-115546CHCF30OCONHCH2-4-Cl—C6H4oil547CHCF30OCONHCH(CH3)C6H5oil548CHCF30OCONHCH2CH2OCH392-94549CHCF30O

190-192550CHCF30OCONHC(CH3)2CCH90-92551CHCF30OCONHCH2-2-Furyl93-95552CHCF30OCON(CH2)391-93553CHCF30OCONHCH2-c-C3H5oil554CHCF30OCONHC(CH3)2CH2CH3oil555CHCF30OCONH(CH2)3C6H5oil556CHCF30OCONHCH2-3-Pyridyl132-134557CHCF30OCON(CH3)-n-C4H9oil558CHCF30OCON(CH2CH3)-i-C3H7oil559CHCF30O

oil560CHCF30OCONHCH2CH2Cloil561CHCF30OCONHCH2CN152-157562CHCF30OCON(CH3)OCH3oil563CHCF30OCON(CH3)CH2CH═CH2oil564CHCF30OCONHCH2COOCH3oil565CHCF30OCON(CH3)-i-C3H7oil566CHCF30OCON(CH3)CH2CH2CNoil567CHCF30OCON(CH3)CH2CH(OCH3)2oil568CHCF30OCON(CH3)CH2CH(—CH2CH2O—)oil569CHCF30OCONHCH2C(═CH2)CHH3oil570CHCF30OCON(CH2CH3)CH2CH═CH2oil571CHCF30OCONHC6H583-85572CHCF30OCON(CH3)CH2CCHoil573CHCF30OCON(CH3)CH2CNoil574CHCF30OCON(CH3)CH2CH2N(CH3)2oil575CHCF30OCONHOCH2CH3114-116576CHCF30OCONHCH2CF374-76577CHCF30OCON(CH2CH2Cl)2oil578CHCF30OCONH-c-C4H7oil579CHCF30OCON(CH2CH2CH3)CH2-c-C3H5oil580CHCF30OCON(CH3)-c-C6H11oil581CHCF30OCON(CH2CH3)CH2C(═CH2)CH3oil582CHCF30OCONHOCH2CH═CH290-92583CHCF30OCONHOCH2C6H5126-128584CHCF30OCON(CH3)CH2COOCH3oil585CHCF30OCOONHCH3230-232586CHCF30OCONHCH2CH383-85587CHCF30OCONHCH(CH3)COOCH3104-106588CHCF30OCONHCH(i-C3H7)COOCH3oil589CHCF30OCON(CH3)CH2CON(CH3)2oil590CHCF30OCON(CH3)-t-C4H9oil591CHCF30OCONHO-t-C4H9103-105592CHCF30OCON(CH3)CH(i-C3H7)COOCH3oil593CHCF30OCH(OCH2CH3)2oil594CHCF30O

oil595CHCF30O

oil596CHCF30O

oil597CHCF30O

oil598CHCF30O

oil599CHCF30OCONHCH2CONHCH3101-103600CHCF30OCON(CH2)7oil601CHCF30OCON(CH2)6oil602CHCF30OCON(CH2CH3)CH2CH2OCH3oil603CHCF30O

oil604CHCF30O

oil605CHCF30O

oil606CHCF30OCON(CH2CH3)CH2CH2CNoil607CHCF30O

oil608CHCF30OCON(CH2CH3)-n-C4H9oil609CHCF30O

179-181610CHCF30OCONHCH(CH3)CONHCH3136-138611CHCF30OCOON(CH2)464-66612CHCF30OCONHCH2CON(CH3)2107-109613CHCF30OCON(CH2COOCH2CH3)2oil614CHCF30O

180-182615CHCF30O

221-223616CHCF30O

234-236617CHCF30O

oil618CHCF30OCON(CH3)CH2-6-Cl-3-pyridyloil619CHCF30O

105-107620CHCF30OCONHCH(CH3)CH(OCH3)2oil621CHCF30OCONHCH2CH2SCH3oil622CHCF30OCONHCH(CH3)CH2OCH370-72623CHCF30OCONHCH2CH2NHCOCH3124-126624CHCF30OCONH(CH2)3OCH2CH3oil625CHCF30OCON(CH2CH3)CH2CH2CH3oil626CHCF30OCON(CH2CH3)CH2OCH3oil627CHCF30OCONHCH2CH2SCH2CH3oil628CHCF30OCONHCH2CH2OCH2CH359-61629CHCF30O

oil630CHCF30O

174-176631CHCF30OCONHCH(CH3)CH(OCH3)2oil632CHCF30OCONHCH2CH2SCH3oil633CHCF30OCONHCH(CH3)CH2OCH370-72634CHCF30OCONHCH2CH2NHCOCH3124-126635CHCF30OCONH(CH2)3OCH2CH3oil636CHCF30OCON(CH2CH3)CH2CH2CH3oil637CHCF30OCON(CH2CH3)CH2OCH3oil638CHCF30OCONHCH2CH2SCH2CH3oil639CHCF30OCONHCH(CH3)CH2COOCH2CH3oil640CHCF30OCONH-4-COOCH3-C6H4189-191641CHCF30OCONH-4-CONH2-C6H4265-267642CHCF30OCONHCH2CH2Broil643CHCF30OCONHCH2CH═CHCH2Cloil644CHCF30OCONH-4-CONHCH3-C6H4219-221645CHCF30OCONHCH2CH2CH2Broil646CHCF30OCONHCH2CH2CH2OCH3oil647CHCF30OCONH-4-CH2CH3—C6H497-99648CHCF30OCONHCH2CH2OCH(CH3)2oil649CHCF30OCONHCH2CH2CH2OCH2CH3oil650CHCF30O

oil651CHCF30O

64-66652CHCF30O

oil653CHCF30O

oil654CHCF30OCH2CON(CH3)CH2CH3oil655CHCF30OCH2CON(CH3)258-60656CHCF30OCH2CON(CH2)4101-103657CHCF30O

oil658CHCF30O

90-92659CHCF30OCH2CONHCH2CH3104-106660CHCF30OCH2CON(CH3)CH2CH2OHoil661CHCF30OCH2CON(CH3)CH2CH2CH3oil662CHCF30OCH2CON(CH3)CH2CH(—OCH2CH2O—)oil663CHCF30OCH2CONHCH2CH3104-106664CHCF30OCH2CON(CH3)CH2CH2OHoil665CHCF30OCH2CON(CH3)CH2CH2CH3oil667CHCF30OCH2CON(CH3)CH2CH(—OCH2CH2O—)oil668CHCF30O

79-81669CHCF30OCH2CONHCH2CH2SCH365-67670CHCF30OCH2CONHCH(CH3)CH2OCH386-88671CHCF30OCON(CH3)CH2CH2OCO-c-C4H7oil672CHCF30OCH2CONHCH2CH2Br87-89673CHCF30OCON(CH3)CH2CH2OCOC6H5oil674CHCF30OCON(CH3)CH2CH2OCO-c-C3H5oil675CHCF30OCONH-2-CH3—C6H4104-106676CHCF30OCH2CON(i-C3H7)-4-F—C6H4102-104677CHCF30O

oil678CHCF30O

100

oil679CHCF30OCON(CH3)CH2CH2OCONHC6H5100-102680CHCF30OCON(CH3)CH2CH2OCONHCH2CH3oil681CHCF30OCON(CH3)CH2CH2OSO2CH3oil682CHCF30OCH2CONH-c-C4H7133-135683CHCF30OCH2CONHCH2CN158-160

[0514]

2

TABLE 2

101

No.
X
Y
W
R1
m.p. [° C.]

684
N
(CF2)3CHF2
O
CH3

685
N
(CF2)2CF3
O
CH2CH3

686
N
(CF2)2CF3
O
COOCH2CH3

687
N
(CF2)2CF3
O
OH

688
N
(CF2)2CF3
O
OCH3

689
N
CF2CF3
O
CH3

690
N
CF2CF3
O
CH2CH3

691
N
CF2CF3
S
CH3

692
N
CF2CF3
S
CH2CH3

693
N
CF2CF3
S
(CH2)2CH3

694
CH
CF3
O
CH3
oil

695
CH
CF3
O
CH2CH3

696
CH
CF3
O
(CH2)2CH3

697
CH
CF3
O
CH(CH3)2

698
CH
CF3
O
(CH2)3CH3

699
CH
CF3
O
CH(CH3)CH2CH3

700
CH
CF3
O
CH2CH(CH3)2

701
CH
CF3
O
C(CH3)3
oil

702
CH
CF3
O
(CH2)4CH3

703
CH
CF3
O
CH(CH3)(CH2)2CH3

704
CH
CF3
O
(CH2)2CH(CH3)2

705
CH
CF3
O
CH2C(CH3)3

706
CH
CF3
O
Cyclo-C5H9

707
CH
CF3
O
Cyclo-C6H11

708
CH
CF3
O
CHO

709
CH
CF3
O
CH═CH2

710
CH
CF3
O
CH2CH═C(CH3)2

711
CH
CF3
O
CH2CH═CH2

712
CH
CF3
O
C(CH3)═CH2

713
CH
CF3
O
(CH2)5C═CH2

714
CH
CF3
O
C(═CHCH3)CH3

715
CH
CF3
O
CH2C≡CH

716
CH
CF3
O
CH2CH2C≡CH

717
CH
CF3
O
CH2C≡CCH2CH3

718
CH
CF3
O
(CH2)4C≡CH

719
CH
CF3
O
CHFCF3

720
CH
CF3
O
COOCH2CH3

721
CH
CF3
O
CH2CH2OH

722
CH
CF3
O
CH2CH2OCH3

723
CH
CF3
O
CH2COOC(CH3)3

724
CH
CF3
O
CH2SC6H5

725
CH
CF3
O
CH2CONHCH3

726
CH
CF3
O
CH2CH(OH)CH2OH

727
CH
CF3
O
CH2COCH3

728
CH
CF3
O
COCH3

729
CH
CF3
O
CH2OC6H5

730
CH
CF3
O
COC6H5

731
CH
CF3
O
CF2CH3

732
CH
CF3
O
CH2CN

733
CH
CF3
O
CH2CH(—O—)CH2

734
CH
CF3
O
CH2(4-OCH3)C6H5

735
CH
CF3
O
CH2CH(OH)CH2SC6H5

736
CH
CF3
O
CH═CF2

737
CH
CF3
O
CCl═CHCl

738
CH
CF3
O
2-Pyridyl

739
CH
CF3
O
OC6H5

740
CH
CF3
O
OH

741
CH
CF3
O
OCH3

742
CH
CF3
O
OCH2CH3

743
CH
CF3
O
OCHF2

744
CH
CF3
O
OCH2C6H5

745
CH
CF3
O
SCH3

746
CH
CF3
O
SC6H5

747
CH
CF3
O
NH2

748
CH
CF3
O
NHCH3

749
CH
CF3
O
NHCH2CH3

750
CH
CF3
O
N(CH2CH3)2

751
CH
CF3
O
N(CH2CN)2

752
CH
CF3
O
N(CH3)2

753
CH
CF3
O
NHCOCH3

754
CH
CF3
O
NHCOCH2CH3

755
CH
CF3
O
OSO2CH3

756
CH
CF3
O
SOCH2(4-Br)—C6H4

757
CH
CF3
O
N(CH3)COOCH2C6H5

758
N
CF3
O
CH3

759
N
CF3
O
CH2CH3

76O
N
CF3
O
(CH2)2CH3

761
N
CF3
O
CH(CH3)2

762
N
CF3
O
(CH2)3CH3

763
N
CF3
O
CH2CH(CH3)2

764
N
CF3
O
C(CH3)3

765
N
CF3
O
CH2C(CH3)3

766
N
CF3
O
Cyclo-C5H9

767
N
CF3
O
Cyclo-C6H11

768
N
CF3
O
CH2C═C(CH3)2

769
N
CF3
O
CH2CH2C═CH2

770
N
CF3
O
CH2CH═CH2

771
N
CF3
O
(CH2)5CH═CH2

772
N
CF3
O
CH2C≡CH

773
N
CF3
O
CH2C≡CCH2CH3

774
N
CF3
O
CHFCF3

775
N
CF3
O
COOCH2CH3

776
N
CF3
O
CH2CH2OH

777
N
CF3
O
CH2CH2OCH3

778
N
CF3
O
CH2COOC(CH3)3

779
N
CF3
O
CH2SC6H5

780
N
CF3
O
CH2CONHCH3

781
N
CF3
O
CH2CH(OH)CH2OH

782
N
CF3
O
CHO

783
N
CF3
O
COCH3

784
N
CF3
O
CH2OC6H5

785
N
CF3
O
COC6H5

786
N
CF3
O
CF2CH3

787
N
CF3
O
CH2CN

788
N
CF3
O
CH2CH2CN

789
N
CF3
O
CH═CF2

790
N
CF3
O
2-Furyl

791
N
CF3
O
OH

792
N
CF3
O
OCH3

793
N
CF3
O
OCH2CH3

794
N
CF3
O
OCHF2

795
N
CF3
O
OCH2C6H5

796
N
CF3
O
NH2

797
N
CF3
O
NHCH3

798
N
CF3
O
NHCH2CH3

799
N
CF3
O
N(CH2CH3)2

800
N
CF3
O
N(CH2CN)2

801
N
CF3
O
N(CH3)2

802
N
CF3
O
NHCOCH3

803
N
CF3
O
NHCOCH2CH3

804
N
CF3
O
OSO2CH3

805
CH
CF3
S
CH3

806
CH
CF3
S
CH2CH3

807
CH
CF3
S
(CH2)2CH3

808
CH
CF3
S
CHO

809
CH
CF3
S
CHFCF3

810
CH
CF3
S
CH2C≡CH

811
CH
CF3
S
COOCH2CH3

812
CH
CF3
S
CH2COOC(CH3)3

813
CH
CF3
S
CH2CN

814
N
CF3
S
CH3

815
N
CF3
S
CH2CH3

816
N
CF3
S
(CH2)2CH3

817
N
CF3
S
CHFCF3

818
N
CF3
S
CH2CH2OH

819
N
CF3
S
CH2COOC(CH3)3

820
N
CH2CH2Cl
O
CH2CH3

821
N
CH2CH2Cl
O
NH2

822
N
CH2Cl
O
CH3

823
CH
CHF2
O
CH3

824
CH
CHF2
O
CH2CH3

825
CH
CHF2
O
(CH2)2CH3

826
CH
CHF2
O
CH2C═CH2

827
CH
CHF2
O
C(CH3)═CH2

828
CH
CHF2
O
COOCH2CH3

829
CH
CHF2
O
CH2CONHCH3

830
CH
CHF2
O
CF2CH3

831
CH
CHF2
O
CHO

832
CH
CHF2
O
NH2

833
CH
CHF2
O
NHCOCH3

834
N
CHF2
O
CH3

835
N
CHF2
O
CH2CH3

836
N
CHF2
O
CH(CH3)(CH2)4CH3

837
N
CHF2
O
CH2CH═CH2

838
N
CHF2
O
COOCH2CH3

839
N
CHF2
O
NH2

[0515]

3

TABLE 3

102

No.
X
Y
m
V
R1
m.p. [° C.]

840
N
(CF2)3CHF2
0
O
CH3

841
N
(CF2)2CF3
0
O
CH2CH3

842
N
(CF2)2CF3
0
O
COOCH2CH3

843
N
(CF2)2CF3
0
O
SH

844
N
(CF2)2CF3
0
O
SCH3

845
N
(CF2)2CF3
0
O
SCH2C≡CH

846
N
CF2CF3
0
O
CH3

847
N
CF2CF3
0
O
CH2CH3

848
N
CF3
0
O
CH3

849
N
CF3
0
O
CH2CH3

850
N
CF3
0
O
(CH2)2CH3

851
N
CF3
0
O
CH(CH3)2

852
N
CF3
0
O
(CH2)3CH3

853
N
CF3
0
O
CH2CH(CH3)2

854
N
CF3
0
O
C(CH3)3

855
N
CF3
0
O
CH2C(CH3)3

856
N
CF3
0
O
Cyclo-C5H9

857
N
CF3
0
O
Cyclo-C6H11

858
N
CF3
0
O
CH2CH═C(CH3)2

859
N
CF3
0
O
CH2CH2CH═CH2

860
N
CF3
0
O
CH2CH═CH2

861
N
CF3
0
O
(CH2)5CH═CH2

862
N
CF3
0
O
CH2C≡CH

863
N
CF3
0
O
CH2C≡CCH2CH3

864
N
CF3
0
O
CHFCF3

865
N
CF3
0
O
COOCH2CH3

866
N
CF3
0
O
CH2CH2OH

867
N
CF3
0
O
CH2CH2OCH3

868
N
CF3
0
O
CH2COOC(CH3)3

869
N
CF3
0
O
CH2SPh

870
N
CF3
0
O
CH2CONHCH3

871
N
CF3
0
O
CH2CH(OH)CH2OH

872
N
CF3
0
O
CHO

873
N
CF3
0
O
COCH3

874
N
CF3
0
O
CH2OC6H5

875
N
CF3
0
O
COPh

876
N
CF3
0
O
CF2CH3

877
N
CF3
0
O
CH2CN

878
N
CF3
0
O
CH2CH2CN

879
N
CF3
0
O
CH═CF2

880
N
CF3
0
O
2-Furyl

881
N
CF3
0
O
OH

882
N
CF3
0
O
OCH3

883
N
CF3
0
O
OCH2CH3

884
N
CF3
0
O
OCHF2

885
N
CF3
0
O
OCH2Ph

886
N
CF3
0
O
NH2

887
N
CF3
0
O
NHCH3

888
N
CF3
0
O
NHCH2CH3

889
N
CF3
0
O
N(CH2CH3)2

890
N
CF3
0
O
N(CH2CN)2

891
N
CF3
0
O
N(CH3)2

892
N
CF3
0
O
NHCOCH3

893
N
CF3
0
O
NHCOCH2CH3

894
N
CF3
0
O
OSO2CH3

895
N
CH2CH2Cl
0
O
CH2CH3

896
N
CH2CH2Cl
0
O
NH2

897
N
CH2Cl
0
O
CH3

898
N
CHF2
0
O
CH3

899
N
CHF2
0
O
CH2CH3

900
N
CHF2
0
O
CH(CH3)(CH2)4CH3

901
N
CHF2
0
O
CH2CH═CH2

902
N
CHF2
0
O
COOCH2CH3

903
N
CHF2
0
O
NH2

904
CH
CF3
0
O
CH3
60-61

905
CH
CF3
1
O
CH3

906
CH
CF3
0
O
CH2CH3
oil

907
CH
CF3
1
O
CH2CH3
oil

908
CH
CF3
0
O
(CH2)2CH3
oil

909
CH
CF3
1
O
(CH2)2CH3
oil

910
CH
CF3
0
O
CH(CH3)2

911
CH
CF3
1
O
CH(CH3)2

912
CH
CF3
0
O
(CH2)3CH3

913
CH
CF3
1
O
(CH2)3CH3

914
CH
CF3
0
O
CH(CH3)CH2CH3

915
CH
CF3
1
O
CH(CH3)CH2CH3

916
CH
CF3
0
O
CH2CH(CH3)2

917
CH
CF3
1
O
CH2CH(CH3)2

918
CH
CF3
0
O
C(CH3)3

919
CH
CF3
1
O
C(CH3)3

920
CH
CF3
0
O
(CH2)4CH3

921
CH
CF3
1
O
(CH2)4CH3

922
CH
CF3
0
O
CH(CH3)(CH2)2CH3

923
CH
CF3
0
O
(CH2)2CH(CH3)2

924
CH
CF3
0
O
CH2C(CH3)3

925
CH
CF3
0
O
cyclo-C5H9

926
CH
CF3
0
O
cyclo-C6H11

927
CH
CF3
0
O
CH2(3-Thienyl)
oil

928
CH
CF3
0
O
CHO

929
CH
CF3
0
O
CH═CH2

930
CH
CF3
0
O
CH2Ph
61-63

931
CH
CF3
0
O
CH2CH═C(CH3)2

932
CH
CF3
0
O
CH2CH═CH2

933
CH
CF3
0
O
C(CH3)═CH2

934
CH
CF3
0
O
(CH2)5C═CH2

935
CH
CF3
0
O
C(═CHCH3)CH3

936
CH
CF3
0
O
CH2C≡CH

937
CH
CF3
0
O
CH2CH2C≡CH2

938
CH
CF3
0
O
CH2C≡CCH2CH3

939
CH
CF3
0
O
(CH2)4C≡CH

940
CH
CF3
0
O
CHFCF3

941
CH
CF3
0
O
COOCH2CH3

942
CH
CF3
0
O
CH2CH2OH

943
CH
CF3
0
O
CH2CH2OCH3

944
CH
CF3
0
O
CH2COOC(CH3)3

945
CH
CF3
0
O
CH2SPh

946
CH
CF3
0
O
CH2CONHCH3

947
CH
CF3
0
O
CH2CH(OH)CH2OH

948
CH
CF3
0
O
CH2COCH3

949
CH
CF3
0
O
COCH3

950
CH
CF3
0
O
CH2Oph

951
CH
CF3
0
O
COPh

952
CH
CF3
0
O
CF2CH3

953
CH
CF3
0
O
CH2CN
oil

954
CH
CF3
0
O
CH2CH(—O—)CH2

955
CH
CF3
0
O
CH2(4-OCH3)Ph

956
CH
CF3
0
O
CH2CH(OH)CH2SPh

957
CH
CF3
0
O
CH═CF2

958
CH
CF3
0
O
CCl═CHCl

959
CH
CF3
0
O
Ph
120-121

960
CH
CF3
0
O
2-Thienyl
87-89

961
CH
CF3
0
O
OPh

962
CH
CF3
0
O
OH

963
CH
CF3
0
O
OCH3

964
CH
CF3
0
O
OCH2CH3

965
CH
CF3
0
O
OCHF2

966
CH
CF3
0
O
OCH2Ph

967
CH
CF3
0
O
SCH3

968
CH
CF3
0
O
SPh

969
CH
CF3
0
O
NH2
190-191

970
CH
CF3
0
O
NHCH3

971
CH
CF3
0
O
NHCH2CH3

972
CH
CF3
0
O
N(CH2CH3)2

973
CH
CF3
0
O
N(CH2CN)2

974
CH
CF3
0
O
N(CH3)2

975
CH
CF3
0
O
NHCOCH3

976
CH
CF3
0
O
NHCOCH2CH3

977
CH
CF3
0
O
OSO2CH3

978
CH
CF3
0
O
SOCH2(4-Br)—C6H4

979
CH
CF3
0
O
N(CH3)COOCH2Ph

980
CH
CF3
0
NCH3
CH3

981
CH
CF3
0
NCH2CH3
CH3

982
CH
CF3
0
NCH2CH3
CH2CH3

983
CH
CF3
0
NCH2CN
CH2CH3

984
CH
CF3
0
NCH2OCH3
NHCH3

985
CH
CF3
0
NCH2OCH2CH3
CN

986
CH
CF3
0
NCH2CH═CH2
CH3

987
CH
CF3
0
NCH2CH═CF2
SCH3

988
CH
CF3
0
NCH2OCH3
SCH2CH3

989
CH
CF3
0
NCH2OCH3
SCH2Ph

990
CH
CHF2
0
O
CH3

991
CH
CHF2
0
O
CH2CH3

992
CH
CHF2
0
O
(CH2)2CH3

993
CH
CHF2
0
O
CH2CH═CH2

994
CH
CHF2
0
O
C(CH3)═CH2

995
CH
CHF2
0
O
COOCH2CH3

996
CH
CHF2
0
O
CH2CONHCH3

997
CH
CHF2
0
O
CF2CH3

998
CH
CHF2
0
O
CHO

999
CH
CHF2
0
O
NH2

1000
CH
CHF2
0
O
NHCOCH3

1001
N
CF2CF3
0
S
CH3

1002
N
CF2CF3
0
S
CH2CH3

1003
N
CF2CF3
0
S
(CH2)2CH3

1004
N
CF3
0
S
CH3

1005
N
CF3
0
S
CH2CH3

1006
N
CF3
0
S
(CH2)2CH3

1007
N
CF3
0
S
CHFCF3

1008
N
CF3
0
S
CH2CH2OH

1009
N
CF3
0
S
CH2COOC(CH3)3

1010
CH
CF3
0
S
CH3

1011
CH
CF3
0
S
CH2CH3

1012
CH
CF3
0
S
(CH2)2CH3

1013
CH
CF3
0
S
CHO

1014
CH
CF3
0
S
CHFCF3

1015
CH
CF3
0
S
CH2C≡CH

1016
CH
CF3
0
S
COOCH2CH3

1017
CH
CF3
0
S
CH2COOC(CH3)3

1018
CH
CF3
0
S
CH2CN

[0516]

4

TABLE 4

103

No.
X
Y
m
V
R2
R3
m.p. [° C.]

1019
N
(CF2)3 CHF2
0
S
H
CH2CH3

1020
N
CF2CF2CF3
0
S
H
CH2CH3

1021
N
CF2CF3
0
S
H
CH2CH3

1022
N
CH2CH2Cl
0
S
H
CH2CH3

1023
N
CH2Cl
0
S
H
CH2CH3

1024
N
CF3
0
S
CH2CH3
CH2CH3

1025
N
CF3
0
S
(CH2)2CH3
H

1026
N
CF3
0
S
CH(CH3)2
H

1027
N
CF3
0
S
CH2CH(CH3)2
H

1028
N
CF3
0
S
C(CH3)3
H

1029
CH
CF3
0
S
H
CH3
oil

1030
CH
CF3
0
S
H
CH2CH3
oil

1031
CH
CF3
0
S
H
C(CH3)3
oil

1032
CH
CF3
0
S
CH2CH3
COOCH2CH3

1033
CH
CF3
0
S
(CH2)2CH3
COOCH2CH3

1034
CH
CF3
0
S
CH(CH3)2
COOCH2CH3

1035
CH
CF3
0
S
CH(CH3)2
CONHCH2CH3

1036
CH
CF3
0
S
CH(CH3)2
CONHCH2CH3

1037
CH
CF3
0
S
CH(CH3)2
CON(CH2CH3)2

1038
CH
CF3
0
S
CH(CH3)2
CONH-cyclo-C3H7

1039
CH
CF3
0
S
C(CH3)3
COOCH2CH3

1040
CH
CF3
0
S
H
CONHCH2CH3

1041
CH
CF3
0
S
H
CON(CH2CH3)2

1042
CH
CF3
0
S
H
COOCH2CH3
oil

1043
CH
CF3
0
S
H
CH2COOCH2CH3
oil

1044
CH
CF3
0
S
H
CH2CHO

1045
CH
CF3
0
S
H
CH2OCH3

1046
CH
CF3
0
S
H
CH2OCH2Ph

1047
CH
CF3
0
S
H
H

1048
CH
CF3
0
S
Cyclo-C5H9
H

1049
CH
CF3
0
S
CON(CH3)2
CH3
oil

1050
CH
CF3
0
S
CH3
CH2CH2OH

1051
CH
CF3
0
S
CH3
CH2CH2OCH3

1052
CH
CF3
0
S
CH3
CH2CH2OCH2Ph

1053
CH
CF3
0
S
CH3
CH2CH2SPh

1054
CH
CF3
0
S
CH3
CH3
oil

1055
CH
CF3
0
S
CH3
CH2CH2CHO

1055
CH
CF3
0
S
CH3
CH2CH2CHNPh

1057
CH
CF3
0
S
CH3
CH2CH2CONH2

1058
CH
CF3
0
S
H
(4-CF3O)C6H4
120-121

1059
CH
CF3
0
S
CH2C≡CH
H

1060
CH
CF3
0
S
CH2CH2C≡CH
H

1061
CH
CF3
0
S
CH2C≡CCH2CH3
H

1062
CH
CF3
0
S
CH2CH═C(CH3)2
H

1063
CH
CF3
0
S
CH2CH2CH═CH2
H

1064
CH
CF3
0
S
CH2CH═CH2
H

1065
CH
CF3
0
S
C(CH3)═CH2
H

1066
CH
CF3
0
S
CHFCF3
H

1067
CH
CF3
0
S
COOCH2CH3
H

1068
CH
CF3
0
S
CH2CH2OH
H

1069
CH
CF3
0
S
CH2CH2OCH3
H

1070
CH
CF3
0
S
CH2COOC(CH3)3
H

1071
CH
CF3
0
S
CH2COCH3
H

1072
CH
CF3
0
S
COCH3
H

1073
CH
CF3
0
S
CH2Oph
H

1074
CH
CF3
0
S
COPh
H

1075
CH
CF3
0
S
CO(4-Cl)—C6H4
H

1076
CH
CF3
0
S
CF2CH3
H

1077
CH
CF3
0
S
CH2CN
H

1078
CH
CF3
0
S
CH2CH2CN
H

1079
N
CF3
0
S
H
H

1080
N
CF3
0
S
H
CH2CH2CN

1081
N
CF3
0
S
H
CH2CO2C(CH3)3

1082
N
CF3
0
S
H
CH2CHO

1083
N
CF3
0
S
H
CH2CH2OH

1084
N
CF3
0
S
H
CH2CH2OCH3

1085
N
CF3
0
S
Cyclo-C5H9
H

1086
N
CF3
0
S
CH3
COOCH2CH3

1087
N
CF3
0
S
CH3
COOH

1088
N
CF3
0
S
CH3
CONH2

1089
N
CF3
0
S
CH3
CONHCH2CH3

1090
N
CF3
0
S
CH3
CON(CH2CH3)2

1091
N
CF3
0
S
CH3
CONHCH3

1092
N
CF3
0
S
CH3
CONHCH2CN

1093
N
CF3
0
S
CH3
CON(CH2CN)2

1094
N
CF3
0
S
CH3
CON(CH3)2

1095
N
CF3
0
S
CH2C≡CH
OCH2CH3

1096
N
CF3
0
S
CH2CH2C≡CH
OCH2CH3

1097
N
CF3
0
S
CH2C≡CCH2CH3
OCH2CH3

1098
N
CF3
0
S
CH2CH═C(CH3)2
OCH2CH3

1099
N
CF3
0
S
CH2CH2CH═CH2
OCH2CH3

1100
N
CF3
0
S
CH2CH═CH2
OCH2CH3

1101
N
CF3
0
S
C(CH3)═CH2
OCH2CH3

1102
N
CF3
0
S
CHFCF3
OCH2CH3

1103
N
CF3
0
S
COOCH2CH3
OCH2CH3

1104
N
CF3
0
S
CH2CH2OH
OCH2CH3

1105
N
CF3
0
S
CH2CH2OCH3
OCH2CH3

1106
N
CF3
0
S
CH2COOC(CH3)3
OCH2CH3

1107
N
CF3
0
S
CH2COCH3
H

1108
N
CF3
0
S
COCH3
H

1109
N
CF3
0
S
CH2Oph
H

1110
N
CF3
0
S
COPh
H

1111
N
CF3
0
S
CO(4-Cl)—C6H4
H

1112
N
CF3
0
S
CF2CH3
H

1113
N
CF3
0
S
CH2CN
H

1114
N
CF3
0
S
CH2CH2CN
H

1115
CH
CF3
0
O
CH2CH3
CH2CH3

1116
CH
CF3
0
O
(CH2)2CH3
H

1117
CH
CF3
0
O
H
CH2CH3
oil

1118
CH
CF3
0
O
CH(CH3)2
COOCH2CH3

1119
CH
CF3
0
O
CH(CH3)2
COOH

1120
CH
CF3
0
O
CH(CH3)2
CONH2

1121
CH
CF3
0
O
CH(CH3)2
CH3

1122
CH
CF3
0
O
C(CH3)3
H

1123
CH
CF3
0
O
H
CH3

1124
CH
CF3
0
O
H
cyclo-C5H9

1125
CH
CF3
0
O
H
CH2CH2CH3

1126
CH
CF3
0
O
H
Ph
103-1041

1127
CH
CF3
0
O
H
2-Pyridyl

1128
CH
CF3
0
O
H
2-Furyl

1129
CH
CF3
0
O
Cyclo-C5H9
H

1130
CH
CF3
0
O
CH3
COOCH2CH3

1131
CH
CF3
0
O
CH3
COOH

1132
CH
CF3
0
O
CH3
CONH2

1133
CH
CF3
0
O
CH3
CONHCH2CH3

1134
CH
CF3
0
O
CH3
CON(CH2CH3)2

1135
CH
CF3
0
O
CH3
CONHCH3

1136
CH
CF3
0
O
CH3
CONHCH2CN

1137
CH
CF3
0
O
CH3
CON(CH2CN)2

1138
CH
CF3
0
O
CH3
CON(CH3)2

1139
CH
CF3
0
O
CH2C≡CH
H

1140
CH
CF3
0
O
CH2CH2C≡CH
H

1141
CH
CF3
0
O
CH2C≡CCH2CH3
H

1142
CH
CF3
0
O
CH2CH═C(CH3)2
H

1143
CH
CF3
0
O
CH2CH2C═CH
H

1144
CH
CF3
0
O
CH2CH═CH2
H

1145
CH
CF3
0
O
C(CH3)═CH2
H

1146
CH
CF3
0
O
CHFCF3
H

1147
CH
CF3
0
O
COOCH2CH3
H

1148
CH
CF3
0
O
CH2CH2OH
H

1149
CH
CF3
0
O
CH2CH2OCH3
H

1150
CH
CF3
0
O
CH2COOC(CH3)3
H

1151
CH
CF3
0
O
CH2COCH3
H

1152
CH
CF3
0
O
COCH3
H

1153
CH
CF3
0
O
CH2Oph
H

1154
CH
CF3
0
O
COPh
H

1155
CH
CF3
0
O
CO(4-Cl)—C6H4
H

1156
CH
CF3
0
O
CF2CH3
H

1157
CH
CF3
0
O
CH2CN
H

1158
CH
CF3
0
O
CH2CH2CN
H

1159
N
CF3
0
O
CH2CH3
CH2CH3

1160
N
CF3
0
O
(CH2)2CH3
H

1161
N
CF3
0
O
CH(CH3)2
CONH2

1162
N
CF3
0
O
CH(CH3)2
CH3

1163
N
CF3
0
O
C(CH3)3
H

1164
N
CF3
0
O
H
CH3

1165
N
CF3
0
O
H
CH2CH3

1166
N
CF3
0
O
H
CH2CH2CH3

1167
N
CF3
0
O
H
Ph

1168
N
CF3
0
O
H
2-Pyridyl

1169
N
CF3
0
O
H
2-Furyl

1170
N
CF3
0
O
Cyclo-C5H9
H

1171
N
CF3
0
O
CH3
COOCH2CH3

1172
N
CF3
0
O
CH3
COOH

1173
N
CF3
0
O
CH3
CONH2

1174
N
CF3
0
O
CH3
CONHCH2CH3

1175
N
CF3
0
O
CH3
CON(CH2CH3)2

1176
N
CF3
0
O
CH3
CONHCH3

1177
N
CF3
0
O
CH3
CONHCH2CN

1178
N
CF3
0
O
CH3
CON(CH2CN)2

1179
N
CF3
0
O
CH3
CON(CH3)2

1180
N
CF3
0
O
CH2C≡CH
H

1181
N
CF3
0
O
CH2CH2C≡CH
H

1182
N
CF3
0
O
CH2C≡CCH2CH3
H

1183
N
CF3
0
O
CH2CH═C(CH3)2
H

1184
N
CF3
0
O
CH2CH2CH═CH2
H

1185
N
CF3
0
O
CH2CH═CH2
H

1186
N
CF3
0
O
C(CH3)═CH2
H

1187
N
CF3
0
O
CHFCF3
H

1188
N
CF3
0
O
COOCH2CH3
H

1189
N
CF3
0
O
CH2CH2OH
H

1190
N
CF3
0
O
CH2CH2OCH3
H

1191
N
CF3
0
O
CH2COOC(CH3)3
H

1192
N
CF3
0
O
CH2COCH3
H

1193
N
CF3
0
O
COCH3
H

1194
N
CF3
0
O
CH2Oph
H

1195
N
CF3
0
O
COPh
H

1196
N
CF3
0
O
CO(4-Cl)—C6H4
H

1197
N
CF3
0
O
CF2CH3
H

1198
N
CF3
0
O
CH2CN
H

1199
N
CF3
0
O
CH2CH2CN
H

1200
N
CF3
0
O
CH2NHSO2CH3
CH3

1201
N
CF3
0
O
(CH2)2NHSO2CH3
CH3

1202
N
CF3
0
O
CH2NHSO2CH2CH3
CH3

1203
N
CF3
0
O
H
CH2NHSO2CH2Ph

1204
CH
CF3
0
O
(CH2)4NHSO2CF3
CH3

1205
CH
CF3
0
O
(CH2)2S(CH2)2CH3
CH2CH2CH3

1206
CH
CF3
0
O
(CH2)4S(CH2)4OCH3
CH3

1207
CH
CF3
0
S
CH3
(CH2)2S(CH2)2CN

1208
CH
CF3
0
S
CH2NHSO2CH2CH3
CH3

1209
CH
CF3
0
S
CH2NHSO2CH2Ph
CH2CH2CH3

1210
CH
CF3
0
S
(CH2)2NHSO2CH3
CF3

1211
CH
CF3
0
S
H
CH2NHSO2CH3

1212
CH
CF3
0
S
CH(CH3)CH2NHPh
CF3

1213
CH
CF3
0
S
(CH2)2S(2-F)—C6H4
CH2CH2CH3

1214
CH
CF3
0
S
(CH2)6NHCH2)6OCH3
CF3

1215
CH
CF3
0
S
H
(CH2)2NH-(2-F)—C6H4

1216
CH
CF3
0
S
(CH2)3NHCH2CN
H

1217
CH
CF3
0
S
(CH2)2O(3-Cl)—C6H4
CH3

1218
CH
CF3
0
S
CF3
(CH2)6NHCH2CF3

1219
CH
CF3
0
S
CH3
(CH2)2O(3-CH3)—C6H4

1220
CH
CF3
0
O
H
CH2NHPh

1221
CH
CF3
0
O
CH3
(CH2)4S(2-Br)—C6H4

1222
CH
CF3
0
O
(CH2)6NH(CH2)2OCH3
CH3

1223
CH
CF3
0
O
(CH2)2NH(CH2)4OCH3
H

1224
CH
CF3
0
O
CF3
(CH2)3NH-(4-CN)—C6H4

1225
CH
CF3
0
O
(CH2)4NHCH2CF3
CH3

1226
CH
CF3
0
O
C2F5
(CH2)2O(3-CH3)—C6H4

1227
CH
CF3
0
O
(CH2)4NHCH2CN
H

1228
CH
CF3
0
O
(CH2)3O(4-Cl)—C6H4
C2F5

[0517]

5

TABLE 5

104

No.
X
Y
V
R4
R5
R6
R7
m.p. [° C.]

1229
CH
CF3
O
H
H
H
H
oil

1230
CH
CF3
O
H
H
CH3
H
oil

1231
CH
CF3
O
H
H
CH2CH3
H
oil

1232
CH
CF3
O
H
H
CH(CH3)2
H

1233
CH
CF3
O
H
H
CH2CH(CH3)2
H

1234
CH
CF3
O
H
H
CH(CH3)CH2CH3
H

1235
CH
CF3
O
H
H
CH2OH
H

1236
CH
CF3
O
H
H
CH(OH)CH3
H

1237
CH
CF3
O
H
H
CH2SH
H

1238
CH
CF3
O
H
H
CH2CH2SCH3
H

1239
CH
CF3
O
H
H
(CH2)3NH2
H

1240
CH
CF3
O
H
H
(CH2)4NH2
H

1241
CH
CF3
O
H
H
CH═CH2
H

1242
CH
CF3
O
H
H
(CH2)2COOCH3
H

1243
CH
CF3
O
H
H
(CH2)2COOH
H

1244
CH
CF3
O
H
H
(CH2)2CONH2
H

1245
CH
CF3
S
CH3
CH3
H
H

1246
CH
CF3
O
H
H
CH3
CH3
oil

1247
CH
CF3
O
H
H
CH2COOCH3
H

1248
CH
CF3
O
H
H
CH2COOH
H

1249
CH
CF3
O
H
H
CH2CONH2
H

1250
CH
CF3
O
H
H
CH2Ph
H

1251
CH
CF3
O
H
H
CH2-(4-OH)—C6H4
H

1252
CH
CF3
O
H
H
CH2-(3-Indolyl)
H

1253
CH
CF3
O
CH3
CH3
H
H
oil

1254
CH
CF3
O
CH3
H
H
H
oil

1255
CH
CF3
O
CH3
H
H
Ph

1256
CH
CF3
O
H

(CH2)4
H

1257
CH
CF3
NH
H

(CH2)4
H

1258
CH
CF3
NCH3
H

(CH2)4
H

1259
CH
CF3
NCH2C6H4
H

(CH2)4
H

1260
CH
CF3
NCH(CH3)2
H

(CH2)4
H

1261
CH
CF3
O
Ph
H
Ph
H

1262
CH
CF3
NH
Ph
H
Ph
H

1263
CH
CF3
NCH3
Ph
H
Ph
H

1264
CH
CF3
NCH2C6H4
Ph
H
Ph
H

1265
N
CF3
O
H
H
CH2CH3
H
oil

1266
N
CF3
O
H
H
CH(CH3)2
H

1267
N
CF3
O
H
H
CH2CH(CH3)2
H

1268
N
CF3
O
H
H
CH2COOH
H

1269
N
CF3
O
H
H
CH2COOCH3
H

1270
N
CF3
O
H
H
CH2CONH2
H

1271
N
CF3
O
CH3
CH3
H
H

1272
N
CF3
O
H
(CH2
H

1273
N
CF3
O
H
H
CH2CH2SCH3
H

1274
CH
CF3
S
H
H
H
H
oil

[0518]

6

TABLE 6

105

m.p.

No.
X
Y
R8
R1
[° C.]

1275
CH
CF3
CH3
SH
209-

210

1276
CH
CF3
CH3
SCH3

1277
CH
CF3
CH3
SCH2CH3

1278
CH
CF3
CH3
S(CH2)2CH3

1279
CH
CF3
CH3
SCH(CH3)2

1280
CH
CF3
CH3
SPh

1281
CH
CF3
CH3
S(CH2)3CH3

1282
CH
CF3
CH3
SCH(CH3)CH2CH3

1283
CH
CF3
CH3
SCH2CH(CH3)2

1284
CH
CF3
CH3
OH
119-

120

1285
CH
CF3
CH3
OCH3

1286
CH
CF3
CH3
OCH2CH3

1287
CH
CF3
CH3
OCHF2

1288
CH
CF3
CH3
OCH2Ph

1289
CH
CF3
CH3
OCONHPh

1290
CH
CF3
CH3
OCONH-(4-F)—C6H4

1291
CH
CF3
CH3
OCONH-(3,5-di-Cl)—C6H3

1292
CH
CF3
CH2CN
OCH3

1293
CH
CF3
CH2CN
OCH2CH3

1294
CH
CF3
CH2CN
OCHF2

1295
CH
CF3
CH2CN
OCH2Ph

1296
CH
CF3
CH2CN
OCONHPh

1297
CH
CF3
CH2CN
OCONH-(4-F)—C6H4

1298
CH
CF3
CH2OCH2CH3
OCH3

1299
CH
CF3
CH2OCH2CH3
OCH2CH3

1300
CH
CF3
CH2OCH2CH3
OCHF2

1301
CH
CF3
CH2OCH2CH3
OCH2Ph

1302
CH
CF3
CH2OCH2CH3
OCONHPh

1303
CH
CF3
H
CH3
203-

204

1304
CH
CF3
H
CH2CH3
134-

135

1305
CH
CF3
H
(CH2)2CH3

1306
CH
CF3
H
CH(CH3)2

1307
CH
CF3
H
Cyclo-C3H5

1308
CH
CF3
H
(CH2)3CH3

1309
CH
CF3
H
CH(CH3)CH2CH3

1310
CH
CF3
H
CH2CH(CH3)2

1311
CH
CF3
H
CH═CH2

1312
CH
CF3
H
CH2CH═C(CH3)2

1313
CH
CF3
H
CH2CH2CH═CH2

1314
CH
CF3
H
CH2CH═CH2

1315
CH
CF3
H
C(CH3)═CH2

1316
CH
CF3
H
CHFCF3

1317
CH
CF3
H
COOCH2CH3

1318
CH
CF3
H
CH2CH2OH

1319
CH
CF3
H
CH2CH2OCH3

1320
CH
CF3
H
CH2COOC(CH3)3

1321
CH
CF3
CH3
CH2COOC(CH3)3

1322
CH
CF3
CH2CN
CH2COOC(CH3)3

1323
CH
CF3
CH2OCH2CH3
CH2COOC(CH3)3

1324
CH
CF3
H
CH2SPh

1325
CH
CF3
H
CH2CONHCH3

1326
CH
CF3
H
CH2COCH3

1327
CH
CF3
H
COCH3

1328
CH
CF3
H
CH2Oph

1329
CH
CF3
H
COPh

1330
CH
CF3
H
CO(3-Cl)—C6H4

1331
CH
CF3
H
CF2CH3

1332
CH
CF3
H
CH2CN

1333
CH
CF3
H
CH2CH2CN

1334
CH
CF3
H
CH2CH(—O—)CH2

1336
CH
CF3
H
CH2(4-OCH3)Ph

1337
N
CF3
CH3
SH

1338
N
CF3
CH3
SCH3

1339
N
CF3
CH3
SCH2CH3

1340
N
CF3
CH3
SPh

1341
N
CF3
CH3
SCH2CH(CH3)2

1342
N
CF3
CH3
OH

1343
N
CF3
CH3
OCH3

1344
N
CF3
CH3
OCH2CH3

1345
N
CF3
CH3
OCH2Ph

1346
N
CF3
CH3
OCONHPh

1347
N
CF3
CH2CN
OCH3

1348
N
CF3
CH2CN
OCH2CH3

1349
N
CF3
CH2CN
OCH2Ph

1350
N
CF3
CH2CN
OCONHPh

1351
N
CF3
CH2OCH2CH3
OCH3

1352
N
CF3
CH2OCH2CH3
OCH2Ph

1353
N
CF3
CH2OCH2CH3
OCONHPh

1354
N
CF3
H
CH3

1355
N
CF3
H
CH2CH3

1356
N
CF3
H
(CH2)2CH3

1357
N
CF3
H
CH(CH3)2

1358
N
CF3
H
(CH2)3CH3

1359
N
CF3
H
CH(CH3)CH2CH3

1360
N
CF3
H
CH2CH(CH3)2

1361
N
CF3
H
CH2C═C(CH3)2

1362
N
CF3
H
CH2CH═CH2

1363
N
CF3
H
C(CH3)H═CH2

1364
N
CF3
H
COOCH2CH3

1365
N
CF3
H
CH2CH2OH

1366
N
CF3
H
CH2CH2OCH3

1367
N
CF3
H
CH2COOC(CH3)3

1368
N
CF3
H
CH2SPh

1369
N
CF3
H
CH2CONHCH3

1370
N
CF3
H
CH2COCH3

1371
N
CF3
H
COCH3

1372
N
CF3
H
CH2Oph

1373
N
CF3
H
COPh

1374
N
CF3
H
CH2CN

1375
N
CF3
H
CH2CH2CN

1376
CH
CF3
CH3
CH2CH3
oil

[0519] C. Biological Examples

Example 1

[0520] 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

[0521] 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 of90-100% among the aphids.

Example 3

[0522] 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

[0523] 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.

[0524] II. Compounds of the Formula (I′)

[0525] A. Chemical Examples

Example 1

[0526] At room temperature, a solution of 4-tridiimidfluoromethylnicotinic acid (2.2 g) in 40 ml of THF was admixed with l,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.).

[0527]

1
H-NMR (DMSO-d6, 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=5Hz, 1H), 9.07 (d, J=5Hz, 1H), 9.30 (s, 1H).

Example 2

[0528] 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.).

[0529]

1
H-NMR (CDCl3, 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=5Hz, 1H), 9.08 (d, J=5Hz, 1H), 9.40 (s, 1H).

Example 3

[0530]

106

[0531] 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

107

[0532] as a slightly yellowish solid (m.p.=214° C.).

[0533]

1
H-NMR (DMSO-d6, 300 MHz): 4.02 (s, 2H), 8.09 (d, J=5H, 1H), 9.15 (d, J=5Hz, 1H), 9.33 (s, 1H).

[0534] 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.

[0535] 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 (MgSO4) and concentration of the dichloromethane phase was purified chromatographically. This gave the desired sulfonamide as a colorless oil.

[0536]

1
H-NMR (CDCl3, 300 MHz): 1.23 (6, J=7Hz, 3H), 2.92 (s, 3H), 3.25 (Q, J=7Hz, 2H), 4.54 (s, 2H), 7.90 (d, J=5Hz, 1H), 9.06 (d, J=5Hz, 1H), 9.35 (s, 1H).

[0537] 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

[0538] 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.

[0539] Water was then added and the mixture was extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO4), 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.

[0540]

1
H-NMR (CDCl3, 300 MHz): 2.88 (t, J=7Hz, 2H), 3.04 (b, s, 1H), 3.82 (t, J=7Hz, 2H), 3.94 (s, 2H), 7.80 (d, J=5Hz, 1H), 9.04 (d, J=5Hz, 1H), 9.35 (s, 1H).

Example 5

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

[0541] 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.

[0542] The reaction mixture was then concentrated, the residue was taken up in ethyl acetate, washed with water, dried (MgSO4), filtered and concentrated.

[0543] Chromatographic purification of the crude product gave the desired ether as a yellowish oil.

[0544]

1
H-NMR (CDCl3, 300 MHz): 1.31 (t, J=7Hz, 3H), 3.72 (t, J=7Hz, 2H), 4.76 (s, 2H), 7.70 (d, J=5Hz, 1H), 9.03 (d, J=5Hz, 1H), 9.33 (s, 1H).

[0545] 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

[0546] 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 MgSO4. 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.

[0547]

1
H-NMR (CDCl3, 300 MHz): 1.38 (t, J=7Hz, 3H), 4.31 (q, J=7Hz, 2H), 5.43 (s, 2H), 7.80 (d, J=5Hz, 1H), 9.04 (d, J=5Hz, 1H), 9.37 (s, 1H).

7TABLE 1

108

Ex. No.YRR′m.p. [° C.]1On-Pr2Oi-Pr3On-Bu4Oi-Buoil5Oallyl6OCH2C≡CH7OCH═CH28OCH2CH2F9OCF310OCH2CF311OCH2CN12Ocyclopropyl13Ocyclopropylmethyl14OCH2CO2Me15OCH2CH2NMe216OCH2-(N-morpholinyl)17O2-chloropyridin-5-yl-methyl18O2-furanyl19O2-pyrimidinyl20O2-oxazolyl21O5-[1,2,4]-oxadiazolyl22Otetrazolyl23SH24SMe25SEt26Sn-Pr27Si-Pr28Sn-Bu29Si-Bu30Sallyl31SCH2C≡CH32SCH═CH233SCH2CH2F34SCF335SCH2CF336SCH2CN37Scyclopropyl38Scyclopropylmethyl39SCH2CO2Me40SCH2CH2NMe241SCH2-(N-morpholinyl)42S2-chloropyridin-5-yl-methyl43S2-furanyl44S2-pyrimidinyl45S2-oxazolyl46S5-[1,2,4]-oxadiazolyl47Stetrazolyl48S(O)Me49S(O)Et50S(O)n-Pr51S(O)i-Pr52S(O)n-Bu53S(O)i-Bu54S(O)allyl55S(O)CH2C≡CH56S(O)CH═CH257S(O)CH2CH2F58S(O)CF359S(O)CH2CF360S(O)CH2CN61S(O)cyclopropyl62S(O)cyclopropylmethyl63S(O)CH2CO2Me64S(O)CH2CH2NMe265S(O)CH2-(N-morpholinyl)66S(O)2-chloropyridin-5-yl-methyl67S(O)2-furanyl68S(O)2-pyrimidinyl69S(O)2-oxazolyl70S(O)5-[1,2,4]-oxadiazolyl71S(O)tetrazolyl72S(O)2Me73S(O)2Et74S(O)2n-Pr75S(O)2i-Pr76S(O)2n-Bu77S(O)2i-Bu78S(O)2allyl79S(O)2CH2C≡CH80S(O)2CH═CH281S(O)2CH2CH2F82S(O)2CF383S(O)2CH2CF384S(O)2CH2CN85S(O)2cyclopropyl86S(O)2cyclopropylmethyl87S(O)2CH2CO2Me88S(O)2CH2CH2NMe289S(O)2CH2-(N-morpholinyl)90S(O)22-chloropyridin-5-yl-methyl91S(O)22-furanyl92S(O)22-pyrimidinyl93S(O)22-oxazolyl94S(O)25-[1,2,4]-oxadiazolyl94aS(O)2tetrazolyl95OC(O)H96OC(O)Me97OC(O)Et98OC(O)n-Pr99OC(O)i-Pr100OC(O)n-Bu101OC(O)i-Bu102OC(O)allyl103OC(O)CH2C≡CH104OC(O)CH═CH2105OC(O)CH2CH2F106OC(O)CF3107OC(O)CH2CF3108OC(O)CH2CN109OC(O)cyclopropyl110OC(O)cyclopropylmethyl111OC(O)CH2CO2Me112OC(O)CH2CH2NMe2113OC(O)CH2-(N-morpholinyl)114OC(O)2-chloropyridin-5-yl-methyl115OC(O)2-furanyl116OC(O)2-pyrimidinyl117OC(O)2-oxazolyl118OC(O)5-[1,2,4]-oxadiazolyl119OC(O)tetrazolyl120OC(O)OMe121OC(O)OEt122OC(O)On-Pr123OC(O)Oi-Pr124OC(O)On-Bu125OC(O)Oi-Bu126OC(O)Oallyl127OC(O)OCH2C≡CH128OC(O)OCH═CH2129OC(O)OCH2CH2F130OC(O)OCF3131OC(O)OCH2CF3132OC(O)OCH2CN133OC(O)Ocyclopropyl134OC(O)Ocyclopropylmethyl135OC(O)OCH2CO2Me136OC(O)OCH2CH2NMe2137OC(O)OCH2-(N-morpholinyl)138OC(O)O2-chloropyridin-5-yl-methyl139OC(O)O2-furanyl140OC(O)O2-pyrimidinyl141OC(O)O2-oxazolyl142OC(O)O5-[1,2,4]-oxadiazolyl143OC(O)Otetrazolyl144OC(O)OCH2CH2OMe145OC(O)NR′HH146OC(O)NR′MeH147OC(O)NR′EtH148OC(O)NR′n-PrH149OC(O)NR′i-PrH150OC(O)NR′n-BuH151OC(O)NR′i-BuH152OC(O)NR′allylH153OC(O)NR′CH2C≡CHH154OC(O)NR′CH═CH2H155OC(O)NR′CH2CH2FH156OC(O)NR′CF3H157OC(O)NR″CH2CF3H158OC(O)NR′CH2CNH159OC(O)NR′cyclopropylH160OC(O)NR′cyclopropylmethylH161OC(O)NR′CH2CO2MeH162OC(O)NR′CH2CH2NMe2H163OC(O)NR′CH2-(N-morpholinyl)H164OC(O)NR′2-chloropyridin-5-yl-methylH165OC(O)NR′2-furanylH166OC(O)NR′2-pyrimidinylH167OC(O)NR′2-oxazolylH168OC(O)NR′5-[1,2,4]-oxadiazolylH169OC(O)NR′tetrazolylH170OC(O)NR′HMe171OC(O)NR′MeMe172OC(O)NR′EtMe173OC(O)NR′n-PrMe174OC(O)NR′i-PrMe175OC(O)NR′n-BuMe176OC(O)NR′i-BuMe177OC(O)NR′allylMe178OC(O)NR′CH2C≡CHMe179OC(O)NR′CH═CH2Me180OC(O)NR′CH2CH2FMe181OC(O)NR′CF3Me182OC(O)NR″CH2CF3Me183OC(O)NR′CH2CNMe184OC(O)NR′cyclopropylMe185OC(O)NR′cyclopropylmethylMe186OC(O)NR′CH2CO2MeMe187OC(O)NR′CH2CH2NMe2Me188OC(O)NR′CH2-(N-morpholinyl)Me189OC(O)NR′2-chloropyridin-5-yl-methylMe190OC(O)NR′2-furanylMe191OC(O)NR′2-pyrimidinylMe192OC(O)NR′2-oxazolylMe193OC(O)NR′5-[1,2,4]-oxadiazolylMe194OC(O)NR′tetrazolylMe195OC(O)NR′HEt196OC(O)NR′MeEt197OC(O)NR′EtEt198OC(O)NR′n-PrEt199OC(O)NR′i-PrEt200OC(O)NR′n-BuEt201OC(O)NR′i-BuEt202OC(O)NR′allylEt203OC(O)NR′CH2C≡CHEt204OC(O)NR′CH═CH2Et205OC(O)NR′CH2CH2FEt206OC(O)NR′CF3Et207OC(O)NR″CH2CF3Et208OC(O)NR′CH2CNEt209OC(O)NR′cyclopropylEt210OC(O)NR′cyclopropylmethylEt211OC(O)NR′CH2CO2MeEt212OC(O)NR′CH2CH2NMe2Et213OC(O)NR′CH2-(N-morpholinyl)Et214OC(O)NR′2-chloropyridin-5-yl-methylEt215OC(O)NR′2-furanylEt216OC(O)NR′2-pyrimidinylEt217OC(O)NR′2-oxazolylEt218OC(O)NR′5-[1,2,4]-oxadiazolylEt219OC(O)NR′tetrazolylEt220OC(O)C(O)OH221OC(O)C(O)OMe222OC(O)C(O)OEt223OC(O)C(O)On-Pr224OC(O)C(O)Oi-Pr225OC(O)C(O)On-Bu226OC(O)C(O)Oi-Bu227OC(O)C(O)Oallyl228OC(O)C(O)OCH2C≡CH229OC(O)C(O)OCH═CH2230OC(O)C(O)OCH2CH2F231OC(O)C(O)OCF3232OC(O)C(O)OCH2CF3234OC(O)C(O)OCH2CN235OC(O)C(O)Ocyclopropyl236OC(O)C(O)Ocyclopropylmethyl237OC(O)C(O)OCH2CO2Me238OC(O)C(O)OCH2CH2NMe2239OC(O)C(O)OCH2-(N-morpholinyl)240OC(O)C(O)O2-chloropyridin-5-yl-methyl241OC(O)C(O)O2-furanyl242OC(O)C(O)O2-pyrimidinyl243OC(O)C(O)O2-oxazolyl244OC(O)C(O)O5-[1,2,4]-oxadiazolyl245OC(O)C(O)Otetrazolyl246S(O)2NR′HH247S(O)2NR′MeH248S(O)2NR′EtH249S(O)2NR′n-PrH250S(O)2NR′i-PrH251S(O)2NR′n-BuH252S(O)2NR′i-BuH253S(O)2NR′allylH254S(O)2NR′CH2C≡CHH255S(O)2NR′CH═CH2H256S(O)2NR′CH2CH2FH257S(O)2NR′CF3H258S(O)2NR′CH2CF3H259S(O)2NR′CH2CNH260S(O)2NR′cyclopropylH261S(O)2NR′cyclopropylmethylH262S(O)2NR′CH2CO2MeH263S(O)2NR′CH2CH2NMe2H264S(O)2NR′CH2-(N-morpholinyl)H265S(O)2NR′2-chloropyridin-5-yl-methylH266S(O)2NR′2-furanylH267S(O)2NR′2-pyrimidinylH268S(O)2NR′2-oxazolylH269S(O)2NR′5-[1,2,4]-oxadiazolylH270S(O)2NR′tetrazolylH271S(O)2NR′HMe272S(O)2NR′MeMe273S(O)2NR′EtMe274S(O)2NR′n-PrMe275S(O)2NR′i-PrMe276S(O)2NR′n-BuMe277S(O)2NR′i-BuMe278S(O)2NR′allylMe279S(O)2NR′CH2C≡CHMe280S(O)2NR′CH═CH2Me281S(O)2NR′CH2CH2FMe282S(O)2NR′CF3Me283S(O)2NR′CH2CF3Me284S(O)2NR′CH2CNMe285S(O)2NR′cyclopropylMe286S(O)2NR′cyclopropylmethylMe287S(O)2NR′CH2CO2MeMe288S(O)2NR′CH2CH2NMe2Me289S(O)2NR′CH2-(N-morpholinyl)Me289S(O)2NR′2-chloropyridin-5-yl-methylMe290S(O)2NR′2-furanylMe291S(O)2NR′2-pyrimidinylMe292S(O)2NR′2-oxazolylMe293S(O)2NR′5-[1,2,4]-oxadiazolylMe294S(O)2NR′tetrazolylMe295S(O)2NR′HEt296S(O)2NR′MeEt297S(O)2NR′EtEt298S(O)2NR′n-PrEt299S(O)2NR′i-PrEt300S(O)2NR′n-BuEt301S(O)2NR′i-BuEt302S(O)2NR′allylEt303S(O)2NR′CH2C≡CHEt304S(O)2NR′CH═CH2Et305S(O)2NR′CH2CH2FEt306S(O)2NR′CF3Et307S(O)2NR′CH2CF3Et308S(O)2NR′CH2CNEt309S(O)2NR′cyclopropylEt310S(O)2NR′cyclopropylmethylEt311S(O)2NR′CH2CO2MeEt312S(O)2NR′CH2CH2NMe2Et313S(O)2NR′CH2-(N-morpholinyl)Et314S(O)2NR′2-chloropyridin-5-yl-methylEt315S(O)2NR′2-furanylEt316S(O)2NR′2-pyrimidinylEt317S(O)2NR′2-oxazolylEt318S(O)2NR′5-[1,2,4]-oxadiazolylEt319S(O)2NR′tetrazolylEt

[0548]

8

TABLE 2

109

Ex. No.
Y
R
R′
m.p. [° 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
CH2C≡CH

oil

9
O
CH═CH2

10
O
CH2CH2F

11
O
CF3

12
O
CH2CF3

oil

13
O
CH2CN

14
O
cyclopropyl

15
O
cyclopropylmethyl

oil

16
O
CH2CO2Me

17
O
CH2CH2NMe2

18
O
CH2-(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
CH2CH2OMe

oil

27
O
CH2CH2OCH2CH2OMe

oil

28
O
CH2CH2SCH2CH3

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
CH2C≡CH

37
S
CH═CH2

38
S
CH2CH2F

39
S
CF3

oil

40
S
CH2CF3

oil

41
S
CH2CN

42
S
cyclopropyl

43
S
cyclopropylmethyl

44
S
CH2CO2Me

oil

45
S
CH2CO2Et

oil

46
S
CH2CH2CO2Me

oil

47
S
CH2CH2NMe2

48
S
CH2-(N-morpholinyl)

49
S
2-chloropyridin-5-yl-methyl

50
S
2-furanyl

51
S
2-pyridinyl

oil

52
S
2-pyrimidinyl

crystalline

53
S
2-oxazolyl

54
S
5-[1,2,4]-oxadiazolyl

55
S
tetrazolyl

56
S
CH2CH2OH

oil

57
S
Ac

oil

58
S

110

59
NR′(CO)

111

136

60
NR′C(O)O
CMe3
H
Öl

61
NR′

112

CO2allyl
Öl

62
NR′SO2
C(H)Cl2
Me
Öl

63
NR′SO2
Bu
Me
Öl

64
NR′SO2
Pr
Me
Öl

65
S
N-Me-imidazol-2-yl

solid

66
S
[1,2,4]-triazol-3-yl

solid

67
5
4-Me-[1,2,4]-triazol-3-yl

crystalline

68
S
4-Me-tetrazol-5-yl

solid

69
S
2-thiazolin-2-yl

crystalline

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)
CH2C≡CH

78
S(O)
CH═CH2

79
S(O)
CH2CH2F

80
S(O)
CF3

solid

CH2CF3

81
S(O)
CH2CN

129

82
S(O)
cyclopropyl

83
S(O)
cyclopropylmethyl

84
S(O)
CH2CO2Me

85
S(O)
CH2CH2NMe2

86
S(O)
CH2-(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
CH2C≡CH

103
S(O)2
CH═CH2

104
S(O)2
CH2CH2F

105
S(O)2
CF3

106
S(O)2
CH2CF3

crystalline

107
S(O)2
CH2CN

108
S(O)2
cyclopropyl

109
S(O)2
cyclopropylmethyl

110
S(O)2
CH2CO2Me

111
S(O)2
CH2CH2NMe2

112
S(O)2
CH2-(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)
CH2C≡CH

133
OC(O)
CH═CH2

oil

134
OC(O)
CH2CH2F

135
OC(O)
CF3

136
OC(O)
CH2CF3

137
OC(O)
CH2CH2SiMe3

oil

138
OC(O)
CH2CN

oil

139
OC(O)
cyclopropyl

140
OC(O)
cyclopropylmethyl

141
OC(O)
CH2CO2Me

oil

142
OC(O)
CH2CH2NMe2

143
OC(O)
CH2OMe

144
OC(O)
CH2-(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
CH2C≡CH

161
OC(O)O
CH═CH2

162
OC(O)O
CH2CH2F

163
OC(O)O
CF3

164
OC(O)O
CH2CF3

165
OC(O)O
CH2CN

166
OC(O)O
cyclopropyl

167
OC(O)O
cyclopropylmethyl

168
OC(O)O
CH2CO2Me

169
OC(O)O
CH2CH2NMe2

170
OC(O)O
CH2-(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′
CH2C≡CH
H

186
OC(O)NR′
CH═CH2
H

187
OC(O)NR′
CH2CH2F
H

188
OC(O)NR′
CF3
H

189
OC(O)NR′
CH2CF3
H

190
OC(O)NR′
CH2CN
H

191
OC(O)NR′
cyclopropyl
H

192
OC(O)NR′
cyclopropylmethyl
H

193
OC(O)NR′
CH2CO2Me
H

194
OC(O)NR′
CH2CH2NMe2
H

195
OC(O)NR′
CH2-(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′
CH2C≡CH
Me

211
OC(O)NR′
CH═CH2
Me

212
OC(O)NR′
CH2CH2F
Me

213
OC(O)NR′
CF3
Me

214
OC(O)NR′
CH2CF3
Me

215
OC(O)NR′
CH2CN
Me

216
OC(O)NR′
cyclopropyl
Me

217
OC(O)NR′
cyclopropylmethyl
Me

218
OC(O)NR′
CH2CO2Me
Me

219
OC(O)NR′
CH2CH2NMe2
Me

220
OC(O)NR′
CH2-(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′
CH2C≡CH
Et

237
OC(O)NR′
CH═CH2
Et

238
OC(O)NR′
CH2CH2F
Et

239
OC(O)NR′
CF3
Et

240
OC(O)NR′
CH2CF3
Et

241
OC(O)NR′
CH2CN
Et

242
OC(O)NR′
cyclopropyl
Et

243
OC(O)NR′
cyclopropylmethyl
Et

244
OC(O)NR′
CH2CO2Me
Et

245
OC(O)NR′
CH2CH2NMe2
Et

246
OC(O)NR′
CH2-(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
CH2C≡CH

263
OC(O)C(O)O
CH═CH2

264
OC(O)C(O)O
CH2CH2F

265
OC(O)C(O)O
CF3

266
OC(O)C(O)O
CH2CF3

267
OC(O)C(O)O
CH2CN

268
OC(O)C(O)O
cyclopropyl

269
OC(O)C(O)O
cyclopropylmethyl

270
OC(O)C(O)O
CH2CO2Me

271
OC(O)C(O)O
CH2CH2NMe2

272
OC(O)C(O)O
CH2-(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)2NR′
H
H

280
S(O)2NR′
Me
H

281
S(O)2NR′
Et
H

282
S(O)2NR′
n-Pr
H

283
S(O)2NR′
i-Pr
H
93

284
S(O)2NR′
n-Bu
H

285
S(O)2NR′
i-Bu
H

286
S(O)2NR′
allyl
H
83

287
S(O)2NR′
CH2C≡CH
H

288
S(O)2NR′
CH═CH2
H

289
S(O)2NR′
CH2CH2F
H

290
S(O)2NR′
CF3
H

291
S(O)2NR′
CH2CF3
H

292
S(O)2NR′
CH2CN
H

293
S(O)2NR′
cyclopropyl
H

294
S(O)2NR′
cyclopropylmethyl
H
solid

295
S(O)2NR′
CH2CO2Me
H

296
S(O)2NR′
CH2CH2NMe2
H

297
S(O)2NR′
CH2-(N-morpholinyl)
H

298
S(O)2NR′
2-chloropyridin-5-yl-methyl
H

299
S(O)2NR′
2-furanyl
H

300
S(O)2NR′
2-pyrimidinyl
H

301
S(O)2NR′
2-oxazolyl
H

302
S(O)2NR′
5-[1,2,4]-oxadiazolyl
H

303
S(O)2NR′
tetrazolyl
H

304
S(O)2NR′
H
Me

305
S(O)2NR′
Me
Me

306
S(O)2NR′
Et
Me
oil

307
S(O)2NR′
n-Pr
Me

308
S(O)2NR′
i-Pr
Me
oil

309
S(O)2NR′
n-Bu
Me

310
S(O)2NR′
i-Bu
Me

311
S(O)2NR′
allyl
Me

312
S(O)2NR′
CH2C≡CH
Me
94

313
S(O)2NR′
CH═CH2
Me

314
S(O)2NR′
CH2CH2F
Me

315
S(O)2NR′
CF3
Me

316
S(O)2NR′
CH2CF3
Me

317
S(O)2NR′
CH2CN
Me

318
S(O)2NR′
cyclopropyl
Me

319
S(O)2NR′
cyclopropylmethyl
Me

320
S(O)2NR′
CH2CO2Me
Me

321
S(O)2NR′
CH2CH2NMe2
Me

322
S(O)2NR′
CH2-(N-morpholinyl)
Me

323
S(O)2NR′
2-chloropyridin-5-yl-methyl
Me

324
S(O)2NR′
furanyl
Me

325
S(O)2NR′
2-pyrimidinyl
Me

326
S(O)2NR′
2-oxazolyl
Me

327
S(O)2NR′
5-[1,2,4]-oxadiazolyl
Me

328
S(O)2NR′
tetrazolyl
Me

329
S(O)2NR′
H
Et

330
S(O)2NR′
Me
Et

331
S(O)2NR′
Et
Et

332
S(O)2NR′
n-Pr
Et

333
S(O)2NR′
i-Pr
Et
70

334
S(O)2NR′
n-Bu
Et

335
S(O)2NR′
i-Bu
Et

336
S(O)2NR′
allyl
Et
oil

337
S(O)2NR′
CH2C≡CH
Et

338
S(O)2NR′
CH═CH2
Et

339
S(O)2NR′
CH2CH2F
Et

340
S(O)2NR′
CF3
Et

341
S(O)2NR′
CH2CF3
Et

342
S(O)2NR′
CH2CN
Et

343
S(O)2NR′
cyclopropyl
Et

344
S(O)2NR′
cyclopropylmethyl
Et

345
S(O)2NR′
CH2CO2Me
Et

346
S(O)2NR′
CH2CH2NMe2
Et

347
S(O)2NR′
CH2-(N-morpholinyl)
Et

348
S(O)2NR′
2-chloropyridin-5-yl-methyl
Et

349
S(O)2NR′
furanyl
Et

350
S(O)2NR′
2-pyrimidinyl
Et

351
S(O)2NR′
2-oxazolyl
Et

352
S(O)2NR′
5-[1,2,4]-oxadiazolyl
Et

353
S(O)2NR′
tetrazolyl
Et

354
S(O)2NR′
n-Pr
n-Pr
oil

355
S(O)2NR′
CH2SCH2CH2
n-Pr

356
S(O)2NR′
CH2CH2CH2CH2CH2
n-Pr
152

357
S(O)2NR′
CH2CH═CHCH2CH2
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-5-yl

oil

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
CO2Et
H
136

373
NR′C(O)
CH(imidazolyl-)CF2C(O)

oil

374
NR′C(O)
CH(Me)CH2C(O)

oil

375
NR′C(O)
CMe2CH2C(O)

oil

376
NR′C(O)
CH(Me)CH(Me)C(O)

oil

377
NR′C(O)
CH2CH2CH2C(O)

oil

378
NR′C(O)
CH(Me)CH2CH2C(O)

oil

379
NR′C(O)
CH2CH(Me)CH2C(O)

oil

380
NR′C(O)
CH2CMe2CH2C(O)

oil

381
NR′C(O)
CH2C[—(CH2)4—]CH2C(O)

oil

382
NR′C(O)

113

192

383
NR′C(O)N(H)
CH(CHMe2)CO2Et
H
oil

384
NR′C(S)N(H)
Et
H
oil

385
NR′C(S)N(H)
CMe3
H
113

386
NR′C(S)N(H)
-p-Tol
H
oil

387
NR′C(O)

114

H
148

388
NR′C(O)N(H)
Et
H
144

389
NR′C(O)N(H)
C(H)Me2
H
159

390
NR′C(O)N(H)
Bu
H
117

391
NR′C(O)N(H)
(CH2)4Me
H
118

392
NR′C(O)N(H)
cyclohexyl
H
160

393
NR′C(O)N(H)
C(H)MeCO2Et
H
157

394
NR′C(O)N(H)
C(O)Ph
H
182

395
NR′C(O)N(H)
(4-CF3—Ph)
H
170

396
NR′C(O)N(H)
(2,6-C6H3F2)
H
193

397
NR′C(O)

115

oil

398
NR′C(O)
CH2C(H)PhCH2C(O)

oil

399
NR′C(O)
CMe═CMeC(O)

oil

400
NR′C(O)

116

oil

401
NR′(CO)N(H)
CMe3
H
120

402
NR′C(O)O
CH2C≡CH
H
solid

403
NR′SO2
C(H)Me2
H
oil

404
NR′C(O)
CH2OC(O)Me
H
80

405
NR′C(O)
(CH2)3Cl
H
56

406
NR′C(O)
(CH2)2SMe
H
96

407
NR′C(O)O
Bu
H
oil

408
NR′C(O)O
cyclopentyl
H
oil

409
NR′C(O)
CH2CH2C(O)

87

410
NR′C(O)N(H)Ph
H
H
129

411
NR′H+HSO4−
H
H
solid

[0549]

9

TABLE 3

117

Ex. No.
Y
R
R′
m.p. [° 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
CH2C≡CH

oil

7
O
CH═CH2

8
O
CH2CH2F

9
O
CF3

10
O
CH2CF3

11
O
CH2CN

12
O
cyclopropyl

13
O
cyclopropylmethyl

14
O
CH2CO2Me

15
O
CH2CH2NMe2

16
O
CH2—(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
CH2C≡CH

32
S
CH═CH2

33
S
CH2CH2F

34
5
CF3

35
S
CH2CF3

oil

36
S
CH2CN

37
S
cyclopropyl

38
S
cyclopropylmethyl

39
S
CH2CO2Me

40
S
CH2CH2NMe2

41
S
CH2-(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

118

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)
CH2C≡CH

58
S(O)
CH═CH2

59
S(O)
CH2CH2F

60
S(O)
CF3

61
S(O)
CH2CF3

62
S(O)
CH2CN

63
S(O)
cyclopropyl

64
S(O)
cyclopropylmethyl

65
S(O)
CH2CO2Me

66
S(O)
CH2CH2NMe2

67
S(O)
CH2—(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
CH2C≡CH

83
S(O)2
CH═CH2

84
S(O)2
CH2CH2F

85
S(O)2
CF3

86
S(O)2
CH2CF3

87
S(O)2
CH2CN

88
S(O)2
cyclopropyl

89
S(O)2
cyclopropylmethyl

90
S(O)2
CH2CO2Me

91
S(O)2
CH2CH2NMe2

92
S(O)2
CH2—(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)
CH2C≡CH

108
OC(O)
CH═CH2

109
OC(O)
CH2CH2F

110
OC(O)
CF3

111
OC(O)
CH2CF3

112
OC(O)
CH2CN

113
OC(O)
cyclopropyl

114
OC(O)
cyclopropylmethyl

115
OC(O)
CH2CO2Me

116
OC(O)
CH2CH2NMe2

117
OC(O)
CH2—(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
CH2C≡CH

133
OC(O)O
CH═CH2

134
OC(O)O
CH2CH2F

135
OC(O)O
CF3

136
OC(O)O
CH2CF3

137
OC(O)O
CH2CN

138
OC(O)O
cyclopropyl

139
OC(O)O
cyclopropylmethyl

140
OC(O)O
CH2CO2Me

141
OC(O)O
CH2CH2NMe2

142
OC(O)O
CH2—(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′
CH2C≡CH
H

160
OC(O)NR′
CH═CH2
H

161
OC(O)NR′
CH2CH2F
H

162
OC(O)NR′
CF3
H

163
OC(O)NR′
CH2CF3
H

164
OC(O)NR′
CH2CN
H

165
OC(O)NR′
cyclopropyl
H

166
OC(O)NR′
cyclopropylmethyl
H

167
OC(O)NR′
CH2CO2Me
H

168
OC(O)NR′
CH2CH2NMe2
H

169
OC(O)NR′
CH2—(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′
CH2C≡CH
Me

186
OC(O)NR′
CH═CH2
Me

187
OC(O)NR′
CH2CH2F
Me

188
OC(O)NR′
CF3
Me

189
OC(O)NR′
CH2CF3
Me

190
OC(O)NR′
CH2CN
Me

191
OC(O)NR′
cyclopropyl
Me

192
OC(O)NR′
cyclopropylmethyl
Me

193
OC(O)NR′
CH2CO2Me
Me

194
OC(O)NR′
CH2CH2NMe2
Me

195
OC(O)NR′
CH2—(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′
CH2C≡CH
Et

212
OC(O)NR′
CH═CH2
Et

213
OC(O)NR′
CH2CH2F
Et

214
OC(O)NR′
CF3
Et

215
OC(O)NR′
CH2CF3
Et

216
OC(O)NR′
CH2CN
Et

217
OC(O)NR′
cyclopropyl
Et

218
OC(O)NR′
cyclopropylmethyl
Et

219
OC(O)NR′
CH2CO2Me
Et

220
OC(O)NR′
CH2CH2NMe2
Et

221
OC(O)NR′
CH2—(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
CH2C≡CH

238
OC(O)C(O)O
CH═CH2

239
OC(O)C(O)O
CH2CH2F

240
OC(O)C(O)O
CF3

241
OC(O)C(O)O
CH2CF3

242
OC(O)C(O)O
CH2CN

243
OC(O)C(O)O
cyclopropyl

244
OC(O)C(O)O
cyclopropylmethyl

245
OC(O)C(O)O
CH2CO2Me

246
OC(O)C(O)O
CH2CH2NMe2

247
OC(O)C(O)O
CH2—(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)2NR′
H
H

256
S(O)2NR′
Me
H

257
S(O)2NR′
Et
H

258
S(O)2NR′
n-Pr
H

259
S(O)2NR′
i-Pr
H

260
S(O)2NR′
n-Bu
H

261
S(O)2NR′
i-Bu
H

262
S(O)2NR′
allyl
H

263
S(O)2NR′
CH2C≡CH
H

264
S(O)2NR′
CH═CH2
H

265
S(O)2NR′
CH2CH2F
H

266
S(O)2NR′
CF3
H

267
S(O)2NR′
CH2CF3
H

268
S(O)2NR′
CH2CN
H

269
S(O)2NR′
cyclopropyl
H

270
S(O)2NR′
cyclopropylmethyl
H

271
S(O)2NR′
CH2CO2Me
H

272
S(O)2NR′
CH2CH2NMe2
H

273
S(O)2NR′
CH2—(N-morpholinyl)
H

274
S(O)2NR′
2-chloropyridin-5-yl-methyl
H

275
S(O)2NR′
n-Hex
H

276
S(O)2NR′
furanyl
H

277
S(O)2NR′
2-pyrimidinyl
H

278
S(O)2NR′
2-oxazolyl
H

279
S(O)2NR′
5-[1,2,4]-oxadiazolyl

280
S(O)2NR′
tetrazolyl

281
S(O)2NR′
H
Me

282
S(O)2NR′
Me
Me

283
S(O)2NR′
Et
Me

284
S(O)2NR′
n-Pr
Me

285
S(O)2NR′
i-Pr
Me

286
S(O)2NR′
n-Bu
Me

287
S(O)2NR′
i-Bu
Me

288
S(O)2NR′
allyl
Me

289
S(O)2NR′
CH2C≡CH
Me

290
S(O)2NR′
CH═CH2
Me

291
S(O)2NR′
CH2CH2F
Me

292
S(O)2NR′
CF3
Me

293
S(O)2NR′
CH2CF3
Me

294
S(O)2NR′
CH2CN
Me

295
S(O)2NR′
cyclopropyl
Me

296
S(O)2NR′
cyclopropylmethyl
Me

297
S(O)2NR′
CH2CO2Me
Me

298
S(O)2NR′
CH2CH2NMe2
Me

299
S(O)2NR′
CH2—(N-morpholinyl)
Me

300
S(O)2NR′
2-chloropyridin-5-yl-methyl
Me

301
S(O)2NR′
n-Hex
Me

302
S(O)2NR′
furanyl
Me

303
S(O)2NR′
2-pyrimidinyl
Me

304
S(O)2NR′
2-oxazolyl
Me

305
S(O)2NR′
5-[1,2,4]-oxadiazolyl
Me

306
S(O)2NR′
tetrazolyl
Me

307
S(O)2NR′
H
Et

308
S(O)2NR′
Me
Et

309
S(O)2NR′
Et
Et

310
S(O)2NR′
n-Pr
Et

311
S(O)2NR′
i-Pr
Et

312
S(O)2NR′
n-Bu
Et

313
S(O)2NR′
i-Bu
Et

314
S(O)2NR′
allyl
Et

315
S(O)2NR′
CH2C≡CH
Et

316
S(O)2NR′
CH═CH2
Et

317
S(O)2NR′
CH2CH2F
Et

318
S(O)2NR′
CF3
Et

319
S(O)2NR′
CH2CF3
Et

320
S(O)2NR′
CH2CN
Et

321
S(O)2NR′
cyclopropyl
Et

322
S(O)2NR′
cyclopropylmethyl
Et

323
S(O)2NR′
CH2CO2Me
Et

324
S(O)2NR′
CH2CH2NMe2
Et

325
S(O)2NR′
CH2—(N-morpholinyl)
Et

326
S(O)2NR′
2-chloropyridin-5-yl-methyl
Et

327
S(O)2NR′
n-Hex
Et

328
S(O)2NR′
furanyl
Et

329
S(O)2NR′
n-Hex
Et

330
S(O)2NR′
2-pyrimidinyl
Et

331
S(O)2NR′
2-oxazolyl
Et

332
S(O)2NR′
5-[1,2,4]-oxadiazolyl
Et

333
S(O)2NR′
tetrazolyl
Et

[0550]

10

TABLE 4

119

Ex. No.
Y
R
R′
m.p. [° 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
CH2C≡CH

10
O
CH═CH2

11
O
CH2CH2F

12
O
CF3

13
O
CH2CF3

14
O
CH2CN

15
O
cyclopropyl

16
O
cyclopropylmethyl

17
O
CH2CO2Me

18
O
CH2CH2NMe2

19
O
CH2—(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
CH2C≡CH

36
S
CH═CH2

37
S
CH2CH2F

38
S
CF3

39
S
CH2CF3

40
S
CH2CN

41
S
cyclopropyl

42
S
cyclopropylmethyl

43
S
CH2CO2Me

44
S
CH2CH2NMe2

45
S
CH2—(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)
CH2C≡CH

62
S(O)
CH═CH2

63
S(O)
CH2CH2F

64
S(O)
CF3

65
S(O)
CH2CF3

66
S(O)
CH2CN

67
S(O)
cyclopropyl

68
S(O)
cyclopropylmethyl

69
S(O)
CH2CO2Me

70
S(O)
CH2CH2NMe2

71
S(O)
CH2—(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
CH2C≡CH

88
S(O)2
CH═CH2

89
S(O)2
CH2CH2F

90
S(O)2
CF3

91
S(O)2
CH2CF3

92
S(O)2
CH2CN

93
S(O)2
cyclopropyl

94
S(O)2
cyclopropylmethyl

95
S(O)2
CH2CO2Me

96
S(O)2
CH2CH2NMe2

97
S(O)2
CH2—(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)
CH2C≡CH

114
OC(O)
CH═CH2

115
OC(O)
CH2CH2F

116
OC(O)
CF3

117
OC(O)
CH2CF3

118
OC(O)
CH2CN

119
OC(O)
cyclopropyl

120
OC(O)
cyclopropylmethyl

121
OC(O)
CH2CO2Me

122
OC(O)
CH2CH2NMe2

123
OC(O)
CH2—(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
CH2C≡CH

140
OC(O)O
CH═CH2

141
OC(O)O
CH2CH2F

142
OC(O)O
CF3

143
OC(O)O
CH2CF3

144
OC(O)O
CH2CN

145
OC(O)O
cyclopropyl

146
OC(O)O
cyclopropylmethyl

147
OC(O)O
CH2CO2Me

148
OC(O)O
CH2CH2NMe2

149
OC(O)O
CH2—(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′
CH2C≡CH
H

166
OC(O)NR′
CH═CH2
H

167
OC(O)NR′
CH2CH2F
H

168
OC(O)NR′
CF3
H

169
OC(O)NR′
CH2CF3
H

170
OC(O)NR′
CH2CN
H

171
OC(O)NR′
cyclopropyl
H

172
OC(O)NR′
cyclopropylmethyl
H

173
OC(O)NR′
CH2CO2Me
H

174
OC(O)NR′
CH2CH2NMe2
H

175
OC(O)NR′
CH2—(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′
CH2C≡CH

192
OC(O)NR′
CH═CH2
Me

193
OC(O)NR′
CH2CH2F
Me

194
OC(O)NR′
CF3
Me

195
OC(O)NR′
CH2CF3
Me

196
OC(O)NR′
CH2CN
Me

197
OC(O)NR′
cyclopropyl
Me

198
OC(O)NR′
cyclopropylmethyl
Me

199
OC(O)NR′
CH2CO2Me
Me

200
OC(O)NR′
CH2CH2NMe2
Me

201
OC(O)NR′
CH2—(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′
CH2C≡CH
Et

218
OC(O)NR′
CH═CH2
Et

219
OC(O)NR′
CH2CH2F
Et

220
OC(O)NR′
CF3
Et

221
OC(O)NR′
CH2CF3
Et

222
OC(O)NR′
CH2CN
Et

223
OC(O)NR′
cyclopropyl
Et

224
OC(O)NR′
cyclopropylmethyl
Et

225
OC(O)NR′
CH2CO2Me
Et

226
OC(O)NR′
CH2CH2NMe2
Et

227
OC(O)NR′
CH2—(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
CH2C≡CH

245
OC(O)C(O)O
CH═CH2

246
OC(O)C(O)O
CH2CH2F

247
OC(O)C(O)O
CF3

248
OC(O)C(O)O
CH2CF3

249
OC(O)C(O)O
CH2CN

250
OC(O)C(O)O
cyclopropyl

251
OC(O)C(O)O
cyclopropylmethyl

252
OC(O)C(O)O
CH2CO2Me

253
OC(O)C(O)O
CH2CH2NMe2

254
OC(O)C(O)O
CH2—(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)2NR′
H
H

263
S(O)2NR′
Me
H

264
S(O)2NR′
Et
H

265
S(O)2NR′
n-Pr
H

266
S(O)2NR′
i-Pr
H

267
S(O)2NR′
n-Bu
H

268
S(O)2NR′
i-Bu
H

269
S(O)2NR′
allyl
H

270
S(O)2NR′
CH2C≡CH
H

271
S(O)2NR′
CH═CH2
H

272
S(O)2NR′
CH2CH2F
H

273
S(O)2NR′
CF3
H

274
S(O)2NR′
CH2CF3
H

275
S(O)2NR′
CH2CN
H

276
S(O)2NR′
cyclopropyl
H

277
S(O)2NR′
cyclopropylmethyl
H

278
S(O)2NR′
CH2CO2Me
H

279
S(O)2NR′
CH2CH2NMe2
H

280
S(O)2NR′
CH2—(N-morpholinyl)
H

281
S(O)2NR′
2-chloropyridin-5-yl-methyl
H

282
S(O)2NR′
n-Hex
H

283
S(O)2NR′
2-furanyl
H

284
S(O)2NR′
2-pyrimidinyl
H

285
S(O)2NR′
2-oxazolyl
H

286
S(O)2NR′
5-[1,2,4]-oxadiazolyl
H

287
S(O)2NR′
tetrazolyl
H

288
S(O)2NR′
H
Me

289
S(O)2NR′
Me
Me

290
S(O)2NR′
Et
Me

300
S(O)2NR′
n-Pr
Me

301
S(O)2NR′
i-Pr
Me

302
S(O)2NR′
n-Bu
Me

303
S(O)2NR′
i-Bu
Me

304
S(O)2NR′
allyl
Me

305
S(O)2NR′
CH2C≡CH
Me

306
S(O)2NR′
CH═CH2
Me

307
S(O)2NR′
CH2CH2F
Me

308
S(O)2NR′
CF3
Me

309
S(O)2NR′
CH2CF3
Me

310
S(O)2NR′
CH2CN
Me

311
S(O)2NR′
cyclopropyl
Me

312
S(O)2NR′
cyclopropylmethyl
Me

313
S(O)2NR′
CH2CO2Me
Me

314
S(O)2NR′
CH2CH2NMe2
Me

315
S(O)2NR′
CH2—(N-morpholinyl)
Me

316
S(O)2NR′
2-chloropyridin-5-yl-methyl
Me

317
S(O)2NR′
n-Hex
Me

318
S(O)2NR′
2-furanyl
Me

319
S(O)2NR′
2-pyrimidinyl
Me

320
S(O)2NR′
2-oxazolyl
Me

321
S(O)2NR′
5-[1,2,4]-oxadiazolyl
Me

322
S(O)2NR′
tetrazolyl
Me

323
S(O)2NR′
H
Et

324
S(O)2NR′
Me
Et

325
S(O)2NR′
Et
Et

326
S(O)2NR′
n-Pr
Et

327
S(O)2NR′
i-Pr
Et

328
S(O)2NR′
n-Bu
Et

329
S(O)2NR′
i-Bu
Et

330
S(O)2NR′
allyl
Et

331
S(O)2NR′
CH2C≡CH
Et

332
S(O)2NR′
CH═CH2
Et

333
S(O)2NR′
CH2CH2F
Et

334
S(O)2NR′
CF3
Et

335
S(O)2NR′
CH2CF3
Et

336
S(O)2NR′
CH2CN
Et

337
S(O)2NR′
cyclopropyl
Et

338
S(O)2NR′
cyclopropylmethyl
Et

339
S(O)2NR′
CH2CO2Me
Et

340
S(O)2NR′
CH2CH2NMe2
Et

341
S(O)2NR′
CH2—(N-morpholinyl)
Et

342
S(O)2NR′
2-chloropyridin-5-yl-methyl
Et

344
S(O)2NR′
n-Hex
Et

345
S(O)2NR′
2-furanyl
Et

346
S(O)2NR′
2-pyrimidinyl
Et

347
S(O)2NR′
2-oxazolyl
Et

348
S(O)2NR′
5-[1,2,4]-oxadiazolyl
Et

349
S(O)2NR′
tetrazolyl
Et

[0551]

11

TABLE 5

120

Ex. No.
Y
R
R′
m.p. [° 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
CH2C≡CH

10
O
CH═CH2

11
O
CH2CH2F

12
O
CF3

13
O
CH2CF3

14
O
CH2CN

15
O
cyclopropyl

16
O
cyclopropylmethyl

17
O
CH2CO2Me

18
O
CH2CH2NMe2

19
O
CH2—(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
CH2C≡CH

35
S
tetrazolyl

36
S
CH═CH2

37
S
CH2CH2F

38
S
CF3

39
S
CH2CF3

40
S
CH2CN

41
S
cyclopropyl

42
S
cyclopropylmethyl

43
S
CH2CO2Me

44
S
CH2CH2NMe2

45
S
CH2—(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)
CH2C≡CH

61
S(O)
CH═CH2

62
S(O)
CH2CH2F

63
S(O)
CF3

64
S(O)
CH2CF3

65
S(O)
CH2CN

66
S(O)
cyclopropyl

67
S(O)
cyclopropylmethyl

68
S(O)
CH2CO2Me

69
S(O)
CH2CH2NMe2

70
S(O)
CH2—(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
CH2C≡CH

87
S(O)2
CH═CH2

88
S(O)2
CH2CH2F

89
S(O)2
CF3

90
S(O)2
CH2CF3

91
S(O)2
CH2CN

92
S(O)2
cyclopropyl

93
S(O)2
cyclopropylmethyl

94
S(O)2
CH2CO2Me

95
S(O)2
CH2CH2NMe2

96
S(O)2
CH2—(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)
CH2C≡CH

113
OC(O)
CH═CH2

114
OC(O)
CH2CH2F

115
OC(O)
CF3

116
OC(O)
CH2CF3

117
OC(O)
CH2CN

118
OC(O)
cyclopropyl

119
OC(O)
cyclopropylmethyl

120
OC(O)
CH2CO2Me

121
OC(O)
CH2CH2NMe2

122
OC(O)
CH2—(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
CH2C≡CH

139
OC(O)O
CH═CH2

140
OC(O)O
CH2CH2F

141
OC(O)O
CF3

142
OC(O)O
CH2CF3

143
OC(O)O
CH2CN

144
OC(O)O
cyclopropyl

145
OC(O)O
cyclopropylmethyl

146
OC(O)O
CH2CO2Me

147
OC(O)O
CH2CH2NMe2

148
OC(O)O
CH2—(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′
CH2C≡CH
H

165
OC(O)NR′
CH═CH2
H

166
OC(O)NR′
CH2CH2F
H

167
OC(O)NR′
CF3
H

168
OC(O)NR′
CH2CF3
H

169
OC(O)NR′
CH2CN
H

170
OC(O)NR′
cyclopropyl
H

171
OC(O)NR′
cyclopropylmethyl
H

172
OC(O)NR′
CH2CO2Me
H

173
OC(O)NR′
CH2CH2NMe2
H

174
OC(O)NR′
CH2—(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′
CH2C≡CH
Me

200
OC(O)NR′
CH═CH2
Me

201
OC(O)NR′
CH2CH2F
Me

202
OC(O)NR′
CF3
Me

203
OC(O)NR′
CH2CF3
Me

204
OC(O)NR′
CH2CN
Me

205
OC(O)NR′
cyclopropyl
Me

206
OC(O)NR′
cyclopropylmethyl
Me

207
OC(O)NR′
CH2CO2Me
Me

208
OC(O)NR′
CH2CH2NMe2
Me

209
OC(O)NR′
CH2—(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′
CH2C≡CH
Et

226
OC(O)NR′
CH═CH2
Et

227
OC(O)NR′
CH2CH2F
Et

228
OC(O)NR′
CF3
Et

229
OC(O)NR′
CH2CF3
Et

230
OC(O)NR′
CH2CN
Et

231
OC(O)NR′
cyclopropyl
Et

232
OC(O)NR′
cyclopropylmethyl
Et

233
OC(O)NR′
CH2CO2Me
Et

234
OC(O)NR′
CH2CH2NMe2
Et

235
OC(O)NR′
CH2—(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
CH2C≡CH

252
OC(O)C(O)O
CH═CH2

253
OC(O)C(O)O
CH2CH2F

254
OC(O)C(O)O
CF3

255
OC(O)C(O)O
CH2CF3

256
OC(O)C(O)O
CH2CN

257
OC(O)C(O)O
cyclopropyl

258
OC(O)C(O)O
cyclopropylmethyl

259
OC(O)C(O)O
CH2CO2Me

260
OC(O)C(O)O
CH2CH2NMe2

261
OC(O)C(O)O
CH2—(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)2NR′
H
Me

270
S(O)2NR′
Me
Me

271
S(O)2NR′
Et
Me

272
S(O)2NR′
n-Pr
Me

273
S(O)2NR′
i-Pr
Me

274
S(O)2NR′
n-Bu
Me

275
S(O)2NR′
i-Bu
Me

276
S(O)2NR′
allyl
Me

277
S(O)2NR′
CH2C≡CH
Me

278
S(O)2NR′
CH═CH2
Me

279
S(O)2NR′
CH2CH2F
Me

280
S(O)2NR′
CF3
Me

281
S(O)2NR′
CH2CF3
Me

282
S(O)2NR′
CH2CN
Me

283
S(O)2NR′
cyclopropyl
Me

284
S(O)2NR′
cyclopropylmethyl
Me

285
S(O)2NR′
CH2CO2Me
Me

286
S(O)2NR′
CH2CH2NMe2
Me

287
S(O)2NR′
CH2—(N-morpholinyl)
Me

288
S(O)2NR′
2-chloropyridin-5-yl-methyl
Me

289
S(O)2NR′
n-Hex
Me

290
S(O)2NR′
2-furanyl
Me

291
S(O)2NR′
2-pyrimidinyl
Me

292
S(O)2NR′
2-oxazolyl
Me

293
S(O)2NR′
5-[1,2,4]-oxadiazolyl
Me

294
S(O)2NR′
tetrazolyl
Me

295
S(O)2NR′
H
Et

296
S(O)2NR′
Me
Et

297
S(O)2NR′
Et
Et

298
S(O)2NR′
n-Pr
Et

299
S(O)2NR′
i-Pr
Et

300
S(O)2NR′
n-Bu
Et

301
S(O)2NR′
i-Bu
Et

302
S(O)2NR′
allyl
Et

303
S(O)2NR′
CH2C≡CH
Et

304
S(O)2NR′
CH═CH2
Et

305
S(O)2NR′
CH2CH2F
Et

306
S(O)2NR′
CF3
Et

307
S(O)2NR′
CH2CF3
Et

308
S(O)2NR′
CH2CN
Et

309
S(O)2NR′
cyclopropyl
Et

310
S(O)2NR′
cyclopropylmethyl
Et

311
S(O)2NR′
CH2CO2Me
Et

312
S(O)2NR′
CH2CH2NMe2
Et

313
S(O)2NR′
CH2—(N-morpholinyl)
Et

314
S(O)2NR′
2-chloropyridin-5-yl-methyl
Et

315
S(O)2NR′
n-Hex
Et

316
S(O)2NR′
2-furanyl
Et

317
S(O)2NR′
2-pyrimidinyl
Et

318
S(O)2NR′
2-oxazolyl
Et

319
S(O)2NR′
5-[1,2,4]-oxadiazolyl
Et

320
S(O)2NR′
tetrazolyl
Et

[0552]

12

TABLE 6

121

Ex. No.
Y
R
R′
m.p. [° 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
CH2C≡CH

10
O
CH═CH2

11
O
CH2CH2F

12
O
CF3

13
O
CH2CF3

14
O
CH2CN

15
O
cyclopropyl

16
O
cyclopropylmethyl

17
O
CH2CO2Me

18
O
CH2CH2NMe2

19
O
CH2—(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
CH2C≡CH

35
S
CH═CH2

36
S
CH2CH2F

37
S
CF3

38
S
CH2CF3

39
S
CH2CN

40
S
cyclopropyl

41
S
cyclopropylmethyl

42
S
CH2CO2Me

43
S
CH2CH2NMe2

44
S
CH2—(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)
CH2C≡CH

60
S(O)
CW═CH2

61
S(O)
CH2CH2F

62
S(O)
CF3

63
S(O)
CH2CF3

64
S(O)
CH2CN

65
S(O)
cyclopropyl

66
S(O)
cyclopropylmethyl

67
S(O)
CH2CO2Me

68
S(O)
CH2CH2NMe2

69
S(O)
CH2—(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
CH2C≡CH

85
S(O)2
CH═CH2

86
S(O)2
CH2CH2F

87
S(O)2
CF3

88
S(O)2
CH2CF3

89
S(O)2
CH2CN

90
S(O)2
cyclopropyl

91
S(O)2
cyclopropylmethyl

92
S(O)2
CH2CO2Me

93
S(O)2
CH2CH2NMe2

94
S(O)2
CH2—(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)
CH2C≡CH

110
OC(O)
CH═CH2

111
OC(O)
CH2CH2F

112
OC(O)
CF3

113
OC(O)
CH2CF3

114
OC(O)
CH2CN

115
OC(O)
cyclopropyl

116
OC(O)
cyclopropylmethyl

117
OC(O)
CH2CO2Me

118
OC(O)
CH2CH2NMe2

119
OC(O)
CH2—(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
CH2C≡CH

135
OC(O)O
CH═CH2

136
OC(O)O
CH2CH2F

137
OC(O)O
CF3

138
OC(O)O
CH2CF3

139
OC(O)O
CH2CN

140
OC(O)O
cyclopropyl

141
OC(O)O
cyclopropylmethyl

142
OC(O)O
CH2CO2Me

143
OC(O)O
CH2CH2NMe2

144
OC(O)O
CH2—(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′
CH2C≡CH
H

160
OC(O)NR′
CH═CH2
H

161
OC(O)NR′
CH2CH2F
H

162
OC(O)NR′
CF3
H

163
OC(O)NR′
CH2CF3
H

164
OC(O)NR′
CH2CN
H

165
OC(O)NR′
cyclopropyl
H

166
OC(O)NR′
cyclopropylmethyl
H

167
OC(O)NR′
CH2CO2Me
H

168
OC(O)NR′
CH2CH2NMe2
H

169
OC(O)NR′
CH2—(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′
CH2C≡CH
Me

185
OC(O)NR′
CH═CH2
Me

186
OC(O)NR′
CH2CH2F
Me

187
OC(O)NR′
CF3
Me

188
OC(O)NR′
CH2CF3
Me

189
OC(O)NR′
CH2CN
Me

190
OC(O)NR′
cyclopropyl
Me

191
OC(O)NR′
cyclopropylmethyl
Me

192
OC(O)NR′
CH2CO2Me
Me

193
OC(O)NR′
CH2CH2NMe2
Me

194
OC(O)NR′
CH2—(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′
CH2C≡CH
Et

210
OC(O)NR′
CH═CH2
Et

211
OC(O)NR′
CH2CH2F
Et

212
OC(O)NR′
CF3
Et

213
OC(O)NR′
CH2CF3
Et

214
OC(O)NR′
CH2CN
Et

215
OC(O)NR′
cyclopropyl
Et

216
OC(O)NR′
cyclopropylmethyl
Et

217
OC(O)NR′
CH2CO2Me
Et

218
OC(O)NR′
CH2CH2NMe2
Et

219
OC(O)NR′
CH—(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
CH2C≡CH

235
OC(O)C(O)O
CH═CH2

236
OC(O)C(O)O
CH2CH2F

237
OC(O)C(O)O
CF3

238
OC(O)C(O)O
CH2CF3

239
OC(O)C(O)O
CH2CN

240
OC(O)C(O)O
cyclopropyl

241
OC(O)C(O)O
cyclopropylmethyl

242
OC(O)C(O)O
CH2CO2Me

243
OC(O)C(O)O
CH2CH2NMe2

244
OC(O)C(O)O
CH2—(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)2NR′
H
H

252
S(O)2NR′
Me
H

253
S(O)2NR′
Et
H

254
S(O)2NR′
n-Pr
H

255
S(O)2NR′
i-Pr
H

256
S(O)2NR′
n-Bu
H

257
S(O)2NR′
i-Bu
H

258
S(O)2NR′
allyl
H

259
S(O)2NR′
CH2C≡CH
H

260
S(O)2NR′
CH═CH2
H

261
S(O)2NR′
CH2CH2F
H

262
S(O)2NR′
CF3
H

263
S(O)2NR′
CH2CF3
H

264
S(O)2NR′
CH2CN
H

265
S(O)2NR′
cyclopropyl
H

266
S(O)2NR′
cyclopropylmethyl
H

267
S(O)2NR′
CH2CO2Me
H

268
S(O)2NR′
CH2CH2NMe2
H

269
S(O)2NR′
CH2—(N-morpholinyl)
H

270
S(O)2NR′
2-chloropyridin-5-yl-methyl
H

271
S(O)2NR′
2-furanyl
H

272
S(O)2NR′
2-pyrimidinyl
H

273
S(O)2NR′
2-oxazolyl
H

274
S(O)2NR′
5-[1,2,4]-oxadiazolyl
H

275
S(O)2NR′
tetrazolyl
H

276
S(O)2NR′
H
Me

277
S(O)2NR′
Me
Me

278
S(O)2NR′
Et
Me

279
S(O)2NR′
n-Pr
Me

280
S(O)2NR′
i-Pr
Me

281
S(O)2NR′
n-Bu
Me

282
S(O)2NR′
i-Bu
Me

283
S(O)2NR′
allyl
Me

284
S(O)2NR′
CH2C≡CH
Me

285
S(O)2NR′
CH═CH2
Me

286
S(O)2NR′
CH2CH2F
Me

287
S(O)2NR′
CF3
Me

288
S(O)2NR′
CH2CF3
Me

289
S(O)2NR′
CH2CN
Me

290
S(O)2NR′
cyclopropyl
Me

291
S(O)2NR′
cyclopropylmethyl
Me

292
S(O)2NR′
CH2CO2Me
Me

293
S(O)2NR′
CH2CH2NMe2
Me

294
S(O)2NR′
CH2—(N-morpholinyl)
Me

295
S(O)2NR′
2-chloropyridin-5-yl-methyl
Me

296
S(O)2NR′
2-furanyl
Me

297
S(O)2NR′
2-pyrimidinyl
Me

298
S(O)2NR′
2-oxazolyl
Me

299
S(O)2NR′
5-[1,2,4]-oxadiazolyl
Me

300
S(O)2NR′
tetrazolyl
Me

301
S(O)2NR′
H
Et

302
S(O)2NR′
Me
Et

303
S(O)2NR′
Et
Et

304
S(O)2NR′
n-Pr
Et

305
S(O)2NR′
i-Pr
Et

306
S(O)2NR′
n-Bu
Et

307
S(O)2NR′
i-Bu
Et

308
S(O)2NR′
allyl
Et

309
S(O)2NR′
CH2C≡CH
Et

310
S(O)2NR′
CH═CH2
Et

311
S(O)2NR′
CH2CH2F
Et

312
S(O)2NR′
CF3
Et

313
S(O)2NR′
CH2CF3
Et

314
S(O)2NR′
CH2CN
Et

315
S(O)2NR′
cyclopropyl
Et

316
S(O)2NR′
cyclopropylmethyl
Et

317
S(O)2NR′
CH2CO2Me
Et

318
S(O)2NR′
CH2CH2NMe2
Et

319
S(O)2NR′
CH2—(N-morpholinyl)
Et

320
S(O)2NR′
2-chloropyridin-5-yl-methyl
Et

321
S(O)2NR′
2-furanyl
Et

322
S(O)2NR′
2-pyrimidinyl
Et

323
S(O)2NR′
2-oxazolyl
Et

324
S(O)2NR′
5-[1,2,4]-oxadiazolyl
Et

325
S(O)2NR′
tetrazolyl
Et

[0553] B. Formulation Examples

[0554] 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.

[0555] 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.

[0556] 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.

[0557] 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.

[0558] 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.

[0559] C. Biological Examples

Example 1

[0560] 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.

[0561] The compounds are numbered with the Table/No. in the table.

Example 2

[0562] 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

[0563] 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.

[0564] 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.

Number	Date	Country	Kind
197 25 450.0	Jun 1997	DE
198 58193.9	Dec 1998	DE

	Number	Date	Country
Parent	09096748	Jun 1998	US
Child	09808194	Mar 2001	US
Parent	09461792	Dec 1999	US
Child	09808194	Mar 2001	US

	Number	Date	Country
Parent	09808194	Mar 2001	US
Child	10056274	Jan 2002	US

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

Information

Publication Number

Date Filed

Date Published

Inventors

CPC

US Classifications

International Classifications

Abstract

Description

Claims

Priority Claims (2)

CROSS-REFERENCE TO RELATED APPLICATIONS

Divisions (2)

Continuation in Parts (1)