4-Haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclyl-pyrimidines, processes for their preparation, compositions comprising them, and their use as pesticides

DESCRIPTION

[0001] 4-Haloalkyl-3-heterocyclylpyridines and 4-haloalkyl--heterocyclyI-pyrimidines, processes for their preparation, compositions comprising them, and their use as pesticides

[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.

[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 93119050 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] 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

[0006] a) in position 5 and is optionally substituted by a thiomethyl group in position 2, or

[0007] b) in position 2 and is optionally substituted in position 4 and 6, in each case by a methyl group.

[0008] 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:

[0009] 3-(2-chlorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole

[0010] 3-(2,6-difluorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole and

[0011] 3-(2-chloro4-fluorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole,

[0012] their desired activity at low application rates, however, is not always satisfactory, especially when controlling insects and spider mites.

[0013] Some commercially available 4-haloalkyl-3-heterocyclylpyridines are known from the Maybridge Catalogue 1996/1997, Maybridge Chemical CO. LTD., Trevillett Tintagel, GB:

[0014] 3-(3,5-dichlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

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

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

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

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

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

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

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

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

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

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

[0025] 5-(2,6-dichloro-4-pyridyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

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

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

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

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

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

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

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

[0033] 2-(4-trifluoromethyl-3-pyridyl)-4-methylthiazolecarbohydrazide

[0034] ethyl 2-(4-trifluoromethyl-3-pyridyl)-4-methylthiazolecarboxylate

[0035] N-(4-chlorophenyl)carbonyl-N′-[2-(4-trifluoromethyl-3-pyridyl)4-methyl-5-thiazolyl]carbonylhydrazine

[0036] 2-(4-trifluoromethyl-3-pyridyl)-4-thiazolecarbohydrazide

[0037] 4-(4-chlorophenyl)-2-(4-trifluoromethyl-3-pyridyl)thiazole

[0038] 4-(4-cyanophenyl)-2-(4-trifluoromethyl-3-py(idyl)thiazole

[0039] N-(4-trifluoromethylphenyl)carbonyl-N′-[2-(4-trifluoromethyl-3-pyridyl)-4-thiazolyl]carbonylhydrazine

[0040] 2-(2-(4-trifluoromethyl-3-pyridyl)thiazolyl)-5-chloro-3-methylbenzo[b]thiophene

[0041] 2-(4-chlorophenylmethylthio)-5-(4-trifluoromethyl-3-pyridyl)-1 -methyl-1 H-1,3,4-triazole

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

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

[0044] However, a biological activity toward harmful organisms has hitherto not been disclosed.

[0045] 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.

[0046] 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.

[0047] In the formula (I):

[0048] Y is halo-C1-C6-alkyl;

[0049] x is CH or N;

[0050] m is 0 or 1;

[0051] Q is a 5-membered heterocyclic group

[0052] in which

1a) X1 = W,X2 = NRa,X3 = CRbR1orb) X1 = NRa,X2 = CRbR1,X3 = Worc) X1 = V,X2 = CRaR1,X3 = NRb ord) X1 = V,X2 = CRaR2,X3 = CRbR3ore) X1 = V,X2 = CR4R5,X3 = CR6R7orf) X1 = NRa,X2 = CRbR1,X3 = NR8;

[0053] Ra and Rb together are a bond

[0054] V is oxygen, sulfur or NR9;

[0055] W is oxygen or sulfur;

[0056] R1 is hydrogen,

[0057] (C1-C20)-alkyl, (C2-C20)-alkenyl, (C2-C20)-alkynyl, (C3-C8)-cycloalkyl,

[0058] (C4-C8)-cycloalkenyl, (C6-C8)-cycloalkynyl,

[0059] where the six last-mentioned radicals are optionally substituted by one or more radicals from the group

[0060] halogen, cyano, nitro, hydroxyl, —C(═W)R10, —C(═NOR10)R10, —(═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—NR10C(═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—R10[(C═W)NR102], —NR10(C═NR10)R10, —NR10(C═NR10)NR102, —O—NR102, —O—NR10(C═W)R10, —SO2NR102, —NR10SO2R10, —SO2OR10, —OSO2R10—OR10, —NR102, —SR10, —SiR103, —SeR10, —PR102, —P(═W)R102, —SOR10, —SO2R10, —PW2R102, —PW3R102, aryl and heterocyclyl, the two last-mentioned radicals optionally being substituted by one or more radicals from the group

[0061] (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, aryl,

[0062] 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,

[0063] where these six abovementioned radicals are optionally substituted by one or more radicals from the group

[0064] halogen, cyano, nitro, —C(═W)R10, —C(═W)OR10, —C(═W)NR102, —OR10, —NR102, —SR10, —SOR10 and —SO2R10,

[0065] halogen, cyano, nitro, —(═W)R10, —C(═W)OR10)R10, —C(═W)NR102)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, heterocyclyl,

[0066] 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,

[0067] where the six abovementioned radicals are optionally substituted by one or more radicals from the group

[0068] cyano, nitro, halogen, —C(═W)R10, —C(═W)OR10, —C(═W)NR102, —NR10C(═W)R10, —N[C(═W)R102, —OC(═W)R10, —OC(═W)OR10, —OR10, —NR102, —SR10, —SOR10 and —SO2R10);

[0069] 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;

[0070] R2 and R3 independently of one another have the definitions given in R1;

[0071] 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;

[0072] 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;

[0073] R5 and R7 independently of one another are hydrogen,

[0074] (C1-C20)-alkyl, (C2-C20)-alkenyl, (C2-C20)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C6-C8)-cycloalkynyl,

[0075] where the six last-mentioned radicals are optionally substituted by one or more radicals from the group

[0076] halogen, cyano, nitro, hydroxyl, —C(═W)R10, —C(═NOR10)R10, —C(═W)NR102)R10, —C(═W)OR10, —C9═W)NR102, —OC(═W)R10, —OC(═W)OR10, —NR10C(═W)R10, —N[C(═W)R10]2, —NR10C(═W)OR10, —C(═W)NR10—NR102, —(═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

[0077] (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, aryl,

[0078] 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,

[0079] where these six abovementioned radicals are optionally substituted by one or more radicals from the group

[0080] halogen, cyano, nitro, —C(═W)R10, —C(═W)OR10, —C(═W)NR102, —OR10, —NR102, —SR10, —SOR10 and —SO2R10;

[0081] 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; pyridyl,

[0082] 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,

[0083] where the six abovementioned radicals are optionally substituted by one or more radicals from the group

[0084] cyano, nitro, halogen, —C(═W)R10, —C(═W)OR10, —C(═W)NR102, —OR10, —NR102, —SR10, —SOR10 and —SO2R10,

[0085] halogen, cyano, nitro, —C(═W)R10, —C(═W)OR10, —C(═W)NR102, —OC(═W)R10, —OR10, —NR102, —SR10, —SOR10 and —S102R10;

[0086] —C(═W)R10, —C(═NOR10)R10, —C(═NNR102)R10, —C(═W)OR10, —C(═W)NR102 or halogen;

[0087] 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; R4 and R5 together form one of the groups ═O, ═S or ═N—R9; 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;

[0088] R6 and R7 together form one of the groups ═O, ═S or ═N—R9;

[0089] R8 is hydrogen, (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-C6)-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,

[0090] where the fourteen last-mentioned radicals are optionally substituted by one or more radicals from the group

[0091] 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)-haloalkyny, sulfnyl, (C3-C8)-cycloalkylsulinyl, (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)- cycoalkylsulfinyl, (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)-halocycloalkenyisulfonyl, (C3-C8)-cycloalkyl-(C1-C4)-alkylsulfonyl, (C4-C8 )-cycloalkenylony-(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, of which the nineteen last-mentioned radicals are optionally substituted in their cyclic moiety by one or more substituents from the group halogen, cyano, nitro, amino, hydroxyl, thio, (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; aryl, which is optionally substituted by one or more radicals from the group 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, (C2-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, (C2-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, —C(═W)R11, OR11 or NR112;

[0092] 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 halogen, cyano, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6) alkynyloxy and (C1-C6)-haloalkyloxy;

[0093] R10 is hydrogen, (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, where the fourteen last-mentioned radicals are optionally substituted by one or more radicals from the group 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)-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)-cycoalkyl-(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)- ycloalkyl-(C2-C4)-alkenylsulfonyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenyl sulfonyl, (C1-C8)-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 )-alkyenyl amino, (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, 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 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;

[0094] aryl, 5- or 6-membered heteroaromatic, where the two last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (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;

[0095] R11 is (C1-C10)-alkyl, haloalkyl, aryl, which is optionally substituted by one or more radicals from the group halogen, cyano, nitro, (C1-C4)-alkoxy, (C1-C4)-alkyl, amino, (C1-C4)-monoalkylamino and (C1-C4)-dialkylamino; NR102, OR10 or SR10.

[0096] The term “halogen” includes fluorine, chlorine, bromine and iodine.

[0097] 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.

[0098] “(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.

[0099] “(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.

[0100] 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.

[0101] “(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.

[0102] 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.

[0103] “(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.

[0104] “(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.

[0105] “(C3-C8)-cycloalkyl-(C1-C6)-alkoxy” is, for example, the cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclohexylethoxy or the cyclohexylbutoxy group;

[0106] The term “(C1-C4)-alkyl-(C3-C8)-cycloalkoxy” is, for example, the methylcyclopropyloxy, methylcyclobutyloxy or the butylcyclohexyloxy group.

[0107] “(C1-C6)-Alkylthio” is an alkylthio group whose hydrocarbon radical has the meaning given under the term “(C1-C6)-alkyl”.

[0108] 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.

[0109] “(C1-C6)-Alkylamino” is a nitrogen atom which is substituted by one or two identical or different alkyl radicals of the above definition.

[0110] 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.

[0111] 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.

[0112] “(C1-C6)-Alkanoyl” is, for example, the acetyl, propionyl, butyryl or 2-methylbutyryl group.

[0113] 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.

[0114] 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, 1,2,4oxadiazole, 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 fulIly unsaturated aromatic heterocyclic compounds.

[0115] “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.

[0116] “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.

[0117] “Aryl-(C1-C4)-alkylthio” is an aryl radical which is attached via an alkylthio radical, for example the benzylthio, naphthylmethylthio or the phenylethylthio radical.

[0118] 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 defition, “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.

[0119] 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.

[0120] Preference is given to those compounds of the formula I in which

[0121] Y is C1-C6-alkyl which is mono- or polysubstituted by chlorine and/or fluorine;

[0122] m is zero;

[0123] Q is a 5-membered heterocyclic group

[0124] in which

[0125] a) X2═NRa and X3═CRbR1 or

[0126] b) X2═CRaR2 and X3═CRbR3 or

[0127] c) X2═CR4R5 and X3═CR6R7;

[0128] Ra and Rb together are a bond;

[0129] R1, R2, R3, R4 and R6 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 A1 consisting of C1-C6-alkylcarbonyl, C1-C6-alkylaminocarbonyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylamino, C1-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;

[0130] 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, SR10 or N(R10)2;

[0131] 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.

[0132] Particular preference is given to compounds of the formula I in which

[0133] Y is trifluoromethyl;

[0134] 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;

[0135] 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;

[0136] 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.

[0137] Very particular preference is given to compounds of the formula I in which

[0138] R1, R2, R3, R 4and 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 A5 are each optionally mono- or polysubstituted by identical or different radicals from the group B2;

[0139] 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.

[0140] 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 KHS04. The salts which can be obtained in this manner likewise have insecticidal, acaricidal and nematicidal properties.

[0141] 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.

[0142] The present invention also provides processes for preparing compounds of the formula I:

[0143] To prepare compounds of the formula (I) in which

[0144] a) X1═W, X2═NRa, X3═CRbR1 and Ra, Rb and R1 are as defined above and W is oxygen, activated derivatives of the acid of the formula (II)

[0145] where X and Y are as defined above, are reacted in the presence of a base with a compound of the formula (III)

[0146] 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.

[0147] 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):

[0148] 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.

[0149] 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′-carbonyidiimidazole.

[0150] 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).

[0151] 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).

[0152] 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.

[0153] To prepare compounds of the formula (I) in which

[0154] b) X1═NRa, X2═CRbR1, X3═W 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.

[0155] To prepare compounds of the formula (I) in which

[0156] c) X1═V, X2═CRaR1, X3═NRb 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.

[0157] 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.

[0158] 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.

[0159] 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.

[0160] To prepare compounds of the formula (I) in which

[0161] d) X1═V, X2═CRaR2, X3═CRbR3 and Ra, Rb and R3 are as defined above and V is oxygen, compounds of the formula (XIV) are reacted with a dehydrating reagent.

[0162] Suitable dehydrating reagents are inorganic acyl chlorides, such as phosphorus oxychloride or thionyl chloride, inorganic acids, such as sulfuric acid or polyphosphoric acid, or a mixture of phosphoric acid and acetic anhydride (Houben-Weyl, Methoden der organischen Chemie, Volume E8a, pages 935-941). The reaction can be carried out with or without a solvent. Suitable solvents are inert solvents, such as toluene, benzene, dimethoxyethane, dimethylformamide, dimethylacetamide and chlorobenzene. The reaction temperature is advantageously in a range between 50° C. and 150° C.

[0163] 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)

[0164] 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.

[0165] To prepare compounds of the formula (I) in which

[0166] e) X1═V, X2═CR4R5, X3═CR6R7 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.

[0167] Compounds of the formual (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.

[0168] An acyl halide or an anhydride can be used as activated derivative of the acid. A number of β-aminoalcohols of the formula (XVI) are commercially available. For others, there is a large number of preparation procedures in the literature, for example a reduction of a-amino acids (B. M. Trost “Comprehensive Organic Synthesis, Reduction”, Volume 8, Pergamon Press, Oxford, 1991). In the abovementioned case e) where V is sulfur, the compounds of the formula (I) can be prepared by reaction of thioamides of the formula (XVII) with compounds of the formula (XIX), the two substituents Z being as defined above and either identical or different (A. R. Katritzky “Comprehensive Heterocyclic Chemistry”, Volume 6, pages 306-312, Pergamon Press, Oxford).

[0169] 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).

[0170] For preparing compounds of the formula (I) in which

[0171] f) X1═NRa, X2═CRbR1, X3═NR8 and Ra, Rb, R1 and R8 are as defined above, hydrazides of the formula (XX)

[0172] 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).

[0173] 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.

[0174] 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.

[0175] 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.

[0176] 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: From the order of the Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp. and Eutetranychus spp.

[0177] From the order of the Isopoda, for example, Oniscus asselus, Armadium vulgar and Porcellio scaber.

[0178] From the order of the Diplopoda, for example, Blaniulus guttulatus.

[0179] From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spp.

[0180] From the order of the Symphyla, for example, Scutigerella immaculate.

[0181] From the order of the Thysanura, for example, Lepisma saccharina.

[0182] From the order of the Collembola, for example, Onychiurus armatus.

[0183] 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.

[0184] From the order of the Isoptera, for example, Reticulitermes spp. From the order of the Anoplura, for example, Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.

[0185] From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea spp.

[0186] From the order of the Thysanoptera, for example, Hercinothrips femoralis, Thrips tabaci and Frankliniella spp.

[0187] From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.

[0188] 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 comi, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.

[0189] 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 citrelIa, 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 mellonelIa, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanimna, Tortrix viridana, Cuaphalocrocis spp. and Manduca spp.

[0190] 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.

[0191] From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

[0192] 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.

[0193] From the order of the Siphonaptera, for example, Xenopsylla cheopsis and Ceratophyllus spp.

[0194] From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans.

[0195] From the class of helminths, for example, Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis, as well as Fasciola.

[0196] From the class of Gastropoda, for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp. and Oncomelania spp.

[0197] From the class of Bivalva, for example, Dreissena spp.

[0198] 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).

[0199] 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.

[0200] 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.

[0201] The compositions according to the invention in general comprise the active compounds of the formula (1) 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:

[0202] 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.

[0203] These individual types of formulation are known in principle and are described, for example, in: Winnacker-Kuchler, “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.

[0204] 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, lnterscience, 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; Schonfeldt, “Grenzflachenaktive Athylenoxidaddukte” [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1967; Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986.

[0205] 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′-dinaphthylmethane6,6′-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.

[0206] 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.

[0207] 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.

[0208] 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.

[0209] 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.

[0210] 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.

[0211] 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.

[0212] The pest control agents include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds, substances produced by microorganisms and the like.

[0213] Preferred partners for the mixtures are

[0214] 1. from the group of phosphorus compounds acephate, azamethiphos, azinphos-ethyl-, azinphosmethyl, bromophos, bromophos-ethyl, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, demeton, demeton-S-methyl, demeton-S-methyl sulfone, dialifos, diazinon, dichlorvos, dicrotophos, O,O-1,2,2,2-tetrachloroethyl phosphorthioate (SD 208 304), dimethoate, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitriothion, fensulfothion, fenthion, fonofos, formothion, heptenophos, isozophos, isothioate, isoxathion, malathion, methacrifos, methamidophos, methidathion, salithion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosfolan, phosmet, phosphamidon, phoxim, pirimiphos, primiphos-ethyl, pirimiphos-methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, suiprofos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorphon, vamidothion;

[0215] 2. from the group of carbamates aldicarb, 2-sec-butylphenyl methylcarbamate (BPMC), carbaryl, carbofuran, carbosulfan, cloethocarb, benfuracarb, ethiofencarb, furathiocarb, isoprocarb, methomyl, 5-methyl-m-cumenyl butyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, ethyl 4,6,9-triaza-4-benzyl-6, 10-dimethyl4-oxa-7-oxo-5, 11-dithia-9-dodecenoate (OK 135), 1-methylthio(ethylideneamino) N-methyl-N-(morpholinothio)carbamate (UC 51717);

[0216] 3. from the group of carboxylic acid esters allethrin, alphametrin, 5-benzyl-3-furylmethyl (E)-(1 R)-cis, 2,2-di-methyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), bioresmethrin, biphenate, (RS)-1-cyano-1-(6-phenoxy-2-pyridyl)methyl (1RS)-trans-3-(4-tert-butylphenyl)-2,2-dimethylcyclopropanecarboxylate (NCI 85193), cycloprothrin, cyhalothrin, cythithrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), permethrin, pheothrin ((R) isomer), d-pralethrin, pyrethrins (naturally occurring products), resmethrin, tefluthrin, tetramethrin and tralomethrin;

[0217] 4. from the group of amidines amitraz, chlordimeform;

[0218] 5. from the group of tin compounds cyhexatin, fenbutatin oxide;

[0219] 6. others abamectin, Bacillus thuringiensis, bensultap, binapacryl, bromopropylate, buprofezin, camphechlor, cartap, chlorobenzilate, chlorfluazuron, 2-(4-chlorophenyl)-4,5-diphenylthiophene (UBI-T 930), chlorfentezine, 2-naphthylmethyl cyclopropanecarboxylate (Ro 12-0470), cyromazin, N-(3,5-dichloro4-(1,1,2,3,3,3-hexafluoro-1-propyloxy)phenyl)carbamoyl)-2-chlorobenzocarboximide acid ethyl ester, dicofol, N-(N-(3,5-i-chloro4-(1,1,2,2-tetrafluoroethoxy)phenylamino)carbonyl)-2,6-difluorobenzamide (XRD 473), diflubenzuron, N-(2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene)-2,4-xylidene, dinobuton, dinocap, endosulfan, ethofenprox, (4-ethoxyphenyl)(dimethyl)(3-(3-phenoxyphenyl)propyl)silane, (4-ethoxyphenyl)(3-(4-fluoro-3-phenoxyphenyl)propyl)dimethylsilane, fenoxycarb, 2-fluoro-5-(4-(4-ethoxyphenyl)4-methyl-1-pentyl)diphenyl ether (MTI 800), granulosis and nuclear polyhedrosis viruses, fenthiocarb, flubenzimine, flucycloxuron, flufenoxuron, gamma-HCH, hexythiazox, hydramethyinon (AC 217300), ivermectin, 2-nitromethyl4,5-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.

[0220] 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.

[0221] 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.

[0222] The active compounds are used in a customary manner appropriate for the use forms.

[0223] 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.

[0224] 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.

[0225] 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).

[0226] 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.

[0227] The examples below serve to illustrate the invention.

[0228] A. Formulation examples

[0229] 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.

[0230] b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of acitve 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.

[0231] 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.

[0232] 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.

[0233] 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.

[0234] B. Chemical examples

[0235] Example No. 1

[0236] 3-Isopropyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4oxadiazole (Table 1, No. 81)

[0237] 2 g of methyl 4-trifluoromethylnicotinate and 1.56 g of isobutyramide oxime were initially charged in 15 ml of ethanol and cooled to 0° C. 10 ml of a 1.2 molar sodium ethoxide solution were added dropwise to this solution. The mixture was allowed to warm to room temperature over a period of two hours and stirring was then continued at this temperature until the reaction, according to TLC, had ended. The reaction mixture was concentrated and the residue was taken up in saturated ammonium chloride solution and extracted with diethyl ether. Chromatographic purification of the crude product gave the desired compound as a yellowish oil. 1H-NMR (CDCl3, 300 MHz): δ=1.41 (d, J=6.9 Hz, 6H), 3.22 (m, 1H), 7.78 (d, J=5 Hz, 1 H), 9.02 (d, J=5 Hz, 1H), 9.34 (s, 1H) ppm.

[0238] Example No. 2

[0239] 3-lsopropyl-5-(4-tifluoromethyl-5pydmidyl)-1,2,4-oxadiazole (Table 1, No. 189)

[0240] 2 g of ethyl 4-trifluoromethylpyrimidine-5-carboxylate and 1.56 g of isobutyramide oxime were intiially 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. 1H-NMR (CDCl3, 300 MHz): δ=1.43 (d, J=7 Hz, 6H), 3.22 (hept., J=7 Hz, 1H), 9.52 (s, 1H), 9.58 (s, 1H) ppm.

[0241] Example No. 3

[0242] 2-Methyl-5-(4-trfluoromethyl-3-pyridyl)-1,3,4-oxadiazole (Table 3, No. 549)

[0243] 500 mg of 4-trifluoromethyinicotinic 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.

[0244]

1
H-NMR (CDCl3, 300 MHz): δ=2.67 (s, 3H), 7.75 (d, J=5 Hz, 1H), 8.99 (d, J=5 Hz, 1H), 9.34 (s, 1H) ppm.

[0245] Example No. 4

[0246] 4-(Ethoxycarbonylmethyl)-2-(4-tifluoromethyl-3-pyridyl)thiazole (Table 4, No. 688)

[0247] 500 mg of 4-trifluoromethylpyridine-3-thiocarboxamide and 440 mg of ethyl 4-chloroacetate were dissolved in 5 ml of dimethylformamide and heated at 100° C. for 4 hours. After cooling, the reaction mixture was poured onto ice-water and extracted with diethyl ether. The diethyl ether phase was dried (MgSO4), filtered and concentrated and the residue was purified by chromatography. This gave the desired product in pure form as a colorless oil.

[0248]

1
H-NMR (CDCl3, 300 MHz): δ=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.

[0249] Example No. 5:

[0250] 4-Ethyl-2-(4-tnfluoromethyl-3-pyndyl)oxazole (Table 4, No. 762)

[0251] 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 9 of 2-amino-i-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-trifluoromethyinicotinamide (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.

[0252]

1
H-NMR (CDCl3, 300 MHz): δ=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.

[0253] Example No. 6

[0254] 4-Ethyl-2-(4-trifiuoromethyl-3-pyridyl)-4,5 dihydrooxazole (Table 5, No 876)

[0255] 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 9 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-trifluoromethyinicotinamide (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.

[0256]

1
H-NMR (CDCl3, 200 MHz): δ=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.

[0257] Example No. 7

[0258] 2-(3-Thienylmethyl)-5(4-tifluoromethyl-3-pyidyl)-1,3,4-oxadiazole (Table 3, No. 572)

[0259] 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.

[0260]

1
H-NMR (CDCl3, 200 MHz): δ=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.

[0261] Example No. 8

[0262] 5Methyl-3-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole (Table 6, No. 947)

[0263] 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.

[0264]

1
H-NMR (CDCl3, 300 MHz): δ=2.58 (s, 3H), 7.64 (d, J=5 Hz,1H), 8.85 (d, J=5 Hz, 1H), 9.19 (s, 1H) ppm.

[0265] Example 9

[0266] 3-(N-Isopropylcarbamoylmethyl)-5-(4-trfluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0267] Step 1: Tert-butyl 3-amino-3-(4-trifluoromethyl-3-pyridinecarbonyloxy-imino)propionate

[0268] 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 9 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.

[0269]

1
H-NMR (CDCl3, 300MHz): δ=1.5 (s, 9H), 3.3 (s, 2H), 5.55 (br.s, 2H), 7.83 (d, J=5 Hz, 1H), 8.97 (d, J=5 Hz, 1H), 9.13 (s, 1H) ppm.

[0270] Step 2: 3-(Tert-butoxycarbonylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0271] 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.

[0272]

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

[0273] Step 3: 3-(Hydroxycarbonylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0274] 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.

[0275] Step 4: 3-(N-Isopropylcarbamoylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0276] 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.

[0277]

1
H-NMR (CDCl3, 300 MHz): δ=1.20 (d, J=7.6 Hz, 6H), 3.82 (s, 2H), 4.12 (m, 1H), 6.50 (br.s, 1H), 7.81 (d, J=5 Hz, 1H), 9.02 (d, J=5 Hz, 1H), 9.37 (s, 1H) ppm.

[0278] Example No. 10

[0279] 3-(N,N-Dimethylaminocarbamoyl)-5-(4-tiifiuoromethyl-3-pyridyl)-1,2,4-oxadiazole (Table 1, No. 502)

[0280] Step 1: Ethyl 2-amino-2-(4-trifluoromethyl-3-pyridinecarbonyloxyimino)acetate

[0281] 17.3 g of carbonyidiimidazole 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 9 of the product as a white solid of mp. 172-174° C.

[0282] Step 2: 3-Ethoxycarbonyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

[0283] 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.

[0284] Step 3: 5-(4-Trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxylic acid

[0285] 15.8 g of 3-ethoxycarbonyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole are initially charged in 13 ml of methanol, and, with ice-cooling at 0° C., a solution of 2.8 g of lithium hydroxide in 50 ml of water is added dropwise. The mixture is stirred at room temperature for 2 h, 20 ml of ice-water are added and the mixture is extracted with 200 ml of diethyl ether. The aqueous phase is adjused to pH═2 using dil. HCl, and the precipitated product is filtered off with suction. After drying, 13.8 g of 5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxylic acid are obtained as a white solid of mp. 157-159° C.

[0286] Step 4: N,N-Dimethyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxamide

[0287] 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.

[0288] In a similar manner, it is possible to prepare the compounds shown in Tables 1 to 6 below.

[0289] The abbreviations used denote

[0290] Ph: phenyl THP: 2-tetrahydropyranyl

2TABLE 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)5CH394CHCF30OO(CH2CH3)2CH395CHCF30OCyclo-C6H1196CHCF30O(CH2)6CH397CHCF30OCH(CH3)(CH2)4CH398CHCF30OCyclo-C7H1399CHCF30OCH2-cyclo-C6H11100CHCF30O2-Norbornyl101CHCF30O(CH2)7CH3102CHCF30OCH(CH2CH3)(CH2)5CH3103CHCF30O(CH2)8CH3104CHCF30O(CH2)3-cycto-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(CH)CH2OH141CHCF30OCH2COCH3142CHCF30OCOCH3143CHCF30OCH2OC6H5144CHCF30OCOC6H5145CHCF30OCO(4-Cl)-C6H4146CHCF30OCF2CH3147CHCF30OCH2CN148CHCF30OCH2CH2CN149CHCF30OCH2CH(—O—)CH2150CHCF30OCH2(4-OCH3)C6H5151CHCF30OCH2-cyclo-(4-Oxo)-C6H8152CHCF30OCH2CH(CH)CH2SC6H5153CHCF30OCH2CH2Si(CH3)3154CHCF30OCH═CF2155CHCF30OCCl═CHCl156CHCF30O2-Pyridyl 99-101157CHCF30O2-Furyl158CHCF30O2-Thienyl106-108159CHCF30OCH2C≡CCH2CH2OTHP160CHCF30OCH2CH2Cloil161CHCF30OSi(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(CH)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)2NHSO2CH3311CHCF30SCH2NHSO2CH3312CHCF30SOH(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)—C6H4oil331CHCF30OCH2SO2C6H5oil332CHCF30OCH2SOCH363333CHCF30OCH2SO—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)CH2CH2CH72-74(CH3)2394CHCF30O

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

190-192398CHCF30OOCH2CON(3-CF3)C6H4136-138399CHCF30OOCH2CON-cyclo-C8H17115-117400CHCF30O

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

Oil406CHCF30OCH2CONCH2CH2OC6H5 99-101407CHCF30OCH2CH═NOCH3oil408CHCF30OCH2CONCH2CH2-[3,4-123-125(OCH3)2]C6H3409CHCF30OCH2CON-(2-Cl)C6H4138-140410CHCF30OCH2CON-(2-SCH3)C6H4136-138411CHCF30O

222-225412CHCF30O

207-209413CHCF30OCH2CON-(3-Br)C6H4129-131414CHCF30OCH2CON—N-(2,4,6-Cl3)C6H2153-155415CHCF30OCH2CON-(4-l)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)oil(CH3)]426CHCF30OCH2CONCH2(4-tert-C4H9)C6H4oil427CHCF30OCH2CONCH(CH3)(tert-C4H9)oil428CHCF30OCH2CONCH(CH3[CH2CH(CH3)(oilCH2CH3)]429CHCF30OCH2CONCH2COOCH2CH3103-105430CHCF30OCH2CON[(CH2)2CH3](CH2-cyclo-oilC3H7)431CHCF30OCH2CONCH(CH3)CH2CH2CH80-82(CH3)2432CHCF30OCH2CONCH(CH2CH3)[CH2CHoil(CH3)2]433CHCF30OCH2C═O-(1-Piperidinyl)oil434CHCF30O

180-182435CHCF30OCH2CONCH2C(═CH2)(CH3)86-87436CHCF30OCH2CONCH[CH(CH3)2](COOoilCH3)437CHCF30OCH2CONCH2-cyclo-C3H7oil438CHCF30OCH2CON(CH2)5OHoil439CHCF30OCH2CON(CH3)(CH2CO2CH3)oil440CHCF30OCH2CON(CH3)(CH2CN)oil441CHCF30OCH2CONCH[CH2CH(CH3)2](CO2oilCH3)442CHCF30OCH2CON-(1-Piperidinyl)oil443CHCF30OCH2CONCH2CH2OCH397-99444CHCF30OCH2CH2SC6H5oil445CHCF30OCH2CH2SCH3oil446CHCF30OCH2CH2SCH2C6H5oil447CHCF30O

oil448CHCF30OCH2CON-(2-OH)C6H4162-164449CHCF30OCH2CON-(3-CH)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-Cl2-4-132-134OCF2CHF2)C6H2490CHCF30OCH2CON-(2,4,5-Cl3)C6H2146491CHCF30OCH2CON-(3,5-Cl2-4-124-126OCF2CHFCF3)C6H2492CHCF30OCH2CON-(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)-C6H2132-134522CHCF30OCHCl2oil523CHCF30OCl3oil524CHCF30OCH(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)CH2CH2CHoil661CHCF30OCH2CON(CH3)CH2CH2CH3oil662CHCF30OCH2CON(CH3)CH2CHoil(—OCH2CH2O—)663CHCF30OCH2CONHCH2CH3104-106664CHCF30OCH2CON(CH3)CH2CH2CHoil665CHCF30OCH2CON(CH3)CH2CH2CH3oil667CHCF30OCH2CON(CH3)CH2CHoil(—OCH2CH2O—)668CHCF30O

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

oil679CHCF30OCON(CH3)CH2CH2OCONHC6H5100-102680CHCF30OCON(CH3)CH2CH2OCONHCH2oilCH3681CHCF30OCON(CH3)CH2CH2OSO2CH3oil682CHCF30OCH2CONH-c-C4H7133-135683CHCF30OCH2CONHCH2CN158-160

[0291]

3

TABLE 2

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)CH2CH

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

760
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

[0292]

4

TABLE 3

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)CH2O

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

[0293]

5

TABLE 4

No.
X
Y
m
V
R2
R3
m.p.

1019
N
(CF2)3CHF2
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
CH2CH2CH

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
103-10

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

[0294]

6

TABLE 5

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
(CH

H

1273
N
CF3
O
H
H
CH2CH2SCH3
H

1274
CH
CF3
S
H
H
H
H
oil

[0295]

7

TABLE 6

No.
X
Y
R8
R1
m.p. [° 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

[0296] C. Biological examples

[0297] Example 1

[0298] 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%.

[0299] Example 2

[0300] Germinated broad bean seeds (Vicia faba) with radicles are transferred into brown glass bottles filled with tap water and subsequently populated with approximately 100 black bean aphids (Aphis fabae) belegt. Plants and aphids are then dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has dripped off, plant and animals are kept in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity. After 3 and 6 days' storage, the effect of the preparation on the aphids is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Example Nos. 79, 78, 80, 81, 83, 84, 88, 133, 135, 136, 137, 138, 139, 1117, 1229, 1230, 1231, 1246 and 1254 effect a mortality of 90-100% among the aphids.

[0301] Example 3

[0302] 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., 4060% 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. 885 139 and 927 effect a mortality of 90-100%.

[0303] Example 4

[0304] 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.

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

4-Haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclyl-pyrimidines, processes for their preparation, compositions comprising them, and their use as pesticides

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Publication Number

Date Filed

Date Published

Inventors

CPC

US Classifications

International Classifications

Abstract

Description

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Priority Claims (1)

Divisions (1)