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

Information

  • Patent Grant
  • 6239160
  • Patent Number
    6,239,160
  • Date Filed
    Friday, June 12, 1998
    26 years ago
  • Date Issued
    Tuesday, May 29, 2001
    23 years ago
Abstract
The present invention relates to 4-haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclylpyrimidines of the formula (I), to processes for their preparation, to compositions comprising them, and to the use of these compounds for controlling animal pests, in particular insects, spider mites, ectoparasites and helminths. In the formula (I), Q is a 5-membered heterocyclic group which is optionally substituted by halogen or organic radicals, Y is halo-C1-C8-alkyl, X is CH or N and m is 0 or 1.
Description




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.




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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




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.




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











In the formula (I):




Y is halo-C


1


-C


6


-alkyl;




X is CH or N;




m is 0 or 1;




Q is a 5-membered heterocyclic group











in which




a) X


1


=W, X


2


=NR


a


, X


3


=CR


b


R


1


or




b) X


1


=NR


a


, X


2


=CR


b


R


1


, X


3


=W or




c) X


1


=V, X


2


=CR


a


R


1


, X


3


=NR


b


or




d) X


1


=V, X


2


=CR


a


R


2


, X


3


=CR


b


R


3


or




e) X


1


=V, X


2


=CR


4


R


5


, X


3


=CR


6


R


7


or




f) X


1


=NR


a


, X


2


=CR


b


R


1


, X


3


=NR


8


;




R


a


and R


b


together are a bond




V is oxygen, sulfur or NR


9


;




W is oxygen or sulfur;




R


1


is hydrogen,




(C


1


-C


20


)-alkyl, (C


2


-C


20


)-alkenyl, (C


2


-C


20


)-alkynyl, (C


3


-C


8


)-cycloalkyl,




(C


4


-C


8


)-cloalkenyl, (C


6


-C


8


)-cycloalkynyl,




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




halogen, cyano, nitro, hydroxyl, —C(═W)R


10


, —C(═NOR


10


)R


10


, —C(═NNR


10




2


)R


10


, —C(═W)OR


10


, —C(═W)NR


10




2


, —OC(═W)R


10


, —OC(═W)OR


10


, —NR


10


C(═W)R


10


, —N[C(═W)R


10


]


2


, —NR


10


C(═W)OR


10


, —C(═W)NR


10


—NR


10




2


, —C(═W)NR


10


[—NR


10


C(═W)R


10


], —NR


10


—C(═W)NR


10




2


, —NR


10


—NR


10


C(═W)R


10


, —NR


10


—N[C(═W)R


10


]


2


, —N[(C═W)R


10


]—NR


10




2


, —NR


10


—NR


10


[(C═W)R


10


], —NR


10


—NR


10


[(C═W)WR


10


], —NR


10


—R


10


[(C═W)NR


10




2


], —NR


10


(C═NR


10


)R


10


, —NR


10


(C═NR


10


)NR


10




2


, —O—NR


10




2


, —O—NR


10


(C═W)R


10


, —SO


2


NR


10




2


, —NR


10


SO


2


R


10


, —SO


2


OR


10


, —OSO


2


R


10


, —OR


10


, —NR


10




2


, —SR


10


, —SiR


10




3


, —SeR


10


, —PR


10




2


, —P(═W)R


10




2


, —SOR


10


, —SO


2


R


10


, —PW


2


R


10




2


, —PW


3


R


10




2


, aryl and heterocyclyl,




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




(C


1


-C


6


)-alkyl, (C


2


-C


6


)-alkenyl, (C


2


-C


6


)-alkynyl, (C


3


-C


8


)-cycloalkyl, (C


4


-C


8


)-cycloalkenyl, (C


6


-C


8


)-cycloalkynyl, (C


1


-C


6


)-haloalkyl, (C


2


-C


6


)-haloalkenyl, (C


2


-C


6


)-haloalkynyl, halogen, —OR


10


, —NR


10




2


, —SR


10


, —SiR


10




3


, —C(═W)R


10


, —C(═W)OR


10


, —C(═W)NR


10




2


, —SOR


10


, —SO


2


R


10


, nitro, cyano and hydroxyl,




aryl,




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




(C


1


-C


6


)-alkyl, (C


2


-C


6


)-alkenyl, (C


2


-C


6


)-alkynyl, (C


3


-C


8


)-cycloalkyl, (C


4


-C


8


)-cycloalkenyl and (C


6


-C


8


)-cycloalkynyl,




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




halogen, cyano, nitro, —C(═W)R


10


, —C(═W)OR


10


, —C(═W)NR


10




2


, —OR


10


, —NR


10




2


, —SR


10


, —SOR


10


and —SO


2


R


10


,




halogen, cyano, nitro, —C(═W)R


10


, —C(═NOR


10


)R


10


, —C(═NNR


10




2


)R


10


, —C(═W)OR


10


, —C(═W)NR


10




2


, —OC(═W)R


10


, —OC(═W)OR


10


, —NR


10


C(═W)R


10


, —N[C(═W)R


10


]


2


, —NR


10


C(═W)OR


10


, —OR


10


, —NR


10




2


, —SR


10


, —SiR


10




3


, —PR


10




2


, —SOR


10


, —SO


2


R


10


, —PW


2


R


10




2


and —PW


3


R


10




2


,




heterocyclyl,




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




(C


1


-C


6


)-alkyl, (C


2


-C


6


)-alkenyl, (C


2


-C


6


)-alkynyl, (C


3


-C


8


)-cycloalkyl, (C


4


-C


8


)-cycloalkenyl and (C


6


-C


8


)-cycloalkynyl,




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




cyano, nitro, halogen, —C(═W)R


10


, —C(═W)OR


10


, —C(═W)NR


10




2


, —NR


10


C(═W)R


10


, —N[C(═W)R


10


]


2


, —OC(═W)R


10


, —OC(═W)OR


10


, —OR


10


, —NR


10




2


, —SR


10


, —SOR


10


and —SO


2


R


10


;




halogen, cyano, nitro, —C(═W)R


10


, —C(═W)OR


10


, —C(═W)NR


10




2


, —OC(═W)R


10


, —OR


10


, —NR


10




2


, —SR


10


, —SOR


10


and —SO


2


R


10


;




—OR


10


, —NR


10




2


, —SR


10


, —SOR


10


, —SO


2


R


10


, —C(═W)R


10


, —C(═NOR


10


)R


10


, —C(═NNR


10




2


)R


10


, —C(═W)OR


10


, —C(═W)NR


10




2


, —OC(═W)R


10


, —OC(═W)OR


10


, —NR


10


C(═W)R


10


, —N[C(═W)R


10


]


2


, —NR


10


C(═W)OR


10


, —C(═W)NR


10


—NR


10




2


, —C(═W)NR


10


—NR


10


[C(═W)R


10


], —NR


10


—C(═W)NR


10




2


, —NR


10


—NR


10


C(═W)R


10


, —NR


10


—NC(═W)R


10




2


, —N(C═W)R


10


—NR


10




2


, —NR


10


—NR


10


[(C═W)R


10


], —NR


10


—NR


10


[(C═W)WR


10


], —NR


10


—NR


10


[(C═W)NR


10




2


], —NR


10


(C═NR


10


)R


10


, —NR


10


(C═NR


10


)NR


10




2


, —O—NR


10




2


, —O—NR


10


(C═W)R


10


, —SO


2


NR


10




2


, —NR


10


SO


2


R


10


, —SO


2


OR


10


, —OSO


2


R


10


, —SC(═W)R


10


, —SC(═W)OR


10


, —SC(═W)R


10


, —PR


10




2


, —PW


2


R


10




2


, —PW


3


R


10




2


, SiR


10




3


or halogen;




R


2


and R


3


independently of one another have the definitions given in R


1


;




R


2


and R


3


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


1


;




R


4


and R


6


independently of one another have the definitions given in R


1


;




R


4


and R


6


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


1


;




R


5


and R


7


independently of one another are hydrogen,




(C


1


-C


20


)-alkyl, (C


2


-C


20


)-alkenyl, (C


2


-C


20


)-alkynyl, (C


3


-C


8


)-cycloalkyl, (C


4


-C


8


)-cycloalkenyl, (C


6


-C


8


)-cycloalkynyl,




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




halogen, cyano, nitro, hydroxyl, —C(═W)R


10


, —C(═NOR


10


)R


10


, —C(═NNR


10




2


)R


10


, —C(═W)OR


10


, —C(═W)NR


10




2


, —OC(═W)R


10


, —OC(═W)OR


10


, —NR


10


C(═W)R


10


, —N[C(═W)R


10


]


2


, —NR


10


C(═W)OR


10


, —C(═W)NR


10


—NR


10




2


, —C(═W)NR


10


—NR


10


[C(═W)R


10


], —NR


10


—C(═W)NR


10




2


, —NR


10


—NR


10


C(═W)R


10


, —NR


10


—N[C(═W)R


10


]


2


, —N[(C═W)R


10


]—NR


10




2


, —NR


10


—NR


10


[(C═W)R


10


], —NR


10


—NR


10


[(C═W)WR


10


], —NR


10


—NR


10


[(C═W)NR


10




2


], —NR


10


(C═NR


10


)R


10


, —NR


10


(C═NR


10


)NR


10




2


, —O—NR


10




2


, —O—NR


10


(C═W)R


10


, —OR


10


, —NR


10




2


, —SR


10


, —SiR


10




3


, —SeR


10


, —PR


10




2


, —P(═W)R


10




2


, —SOR


10


, —SO


2


R


10


, —PW


2


R


10




2


, —PW


3


R


10




2


, aryl and heterocyclyl,




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




(C


1


-C


6


)-alkyl, (C


2


-C


6


)-alkenyl, (C


2


-C


6


)-alkynyl, (C


3


-C


8


)-cycloalkyl, (C


4


-C


8


)-cycloalkenyl, (C


6


-C


8


)-cycloalkynyl, (C


1


-C


6


)-haloalkyl, (C


2


-C


6


)-haloalkenyl, (C


2


-C


6


)-haloalkynyl, halogen, —OR


10


, —NR


10




2


, —SR


10


, —SiR


10




3


, —C(═W)R


10


, —C(═W)OR


10


, —C(═W)NR


10




2


, —SOR


10


, —SO


2


R


10


, nitro, cyano and hydroxyl,




aryl,




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




(C


1


-C


6


)-alkyl, (C


2


-C


6


)-alkenyl, (C


2


-C


6


)-alkynyl, (C


3


-C


8


)-cycloalkyl, (C


4


-C


8


)-cycloalkenyl and (C


6


-C


8


)-cycloalkynyl,




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




halogen, cyano, nitro, —C(═W)R


10


, —C(═W)OR


10


, —C(═W)NR


10




2


, —OR


10


, —NR


10




2


, —SR


10


, —SOR


10


and —SO


2


R


10


;




halogen, cyano, nitro, —C(═W)R


10


, —C(═NOR


10


)R


10


, —C(═NNR


10




2


)R


10


, —C(═W)OR


10


, —C(═W)NR


10




2


, —OC(═W)R


10


, —OC(═W)OR


10


, —NR


10


C(═W)R


10


, —N[C(═W)R


10


]


2


, —NR


10


C(═W)OR


10


, —OR


10


, —NR


10




2


, —SR


10


, —SiR


10




3


, —PR


10




2


, —SOR


10


, —SO


2


R


10


, —PW


2


R


10




2


and —PW


3


R


10




2


;




pyridyl,




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




(C


1


-C


6


)-alkyl, (C


2


-C


6


)-alkenyl, (C


2


-C


6


)-alkynyl, (C


3


-C


8


)-cycloalkyl, (C


4


-C


8


)-cycloalkenyl and (C


6


-C


8


)-cycloalkynyl,




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




cyano, nitro, halogen, —C(═W)R


10


, —C(═W)OR


10


, —C(═W)NR


10




2


, —OR


10


, —NR


10




2


, —SR


10


, —SOR


10


and —SO


2


R


10


,




halogen, cyano, nitro, —C(═W)R


10


, —C(═W)OR


10


, —C(═W)NR


10




2


, —OC(═W)R


10


, —OR


10


, —NR


10




2


, —SR


10


, —SOR


10


and —SO


2


R


10


;




—C(═W)R


10


, —C(═NOR


10


)R


10


, —C(═NNR


10




2


)R


10


, —C(═W)OR


10


, —C(═W)NR


10




2


or halogen;




R


4


and R


5


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


1


;




R


4


and R


5


together form one of the groups ═O, ═S or ═N—R


9


;




R


6


and R


7


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


1


;




R


6


and R


7


together form one of the groups ═O, ═S or ═N—R


9


;




R


8


is hydrogen,




(C


1


-C


6


)-alkyl, (C


2


-C


6


)-alkenyl, (C


2


-C


6


)-alkynyl, (C


3


-C


8


)-cycloalkyl, (C


4


-C


8


)-cycloalkenyl, (C


3


-C


8


)-cycloalkyl-(C


1


-C


4


)-alkyl, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkyl, (C


3


-C


8


)-cycloalkyl-(C


2


-C


4


)-alkenyl, (C


4


-C


8


)-Cycloalkenyl-(C


1


-C


4


)-alkenyl, (C


1


-C


6


)-alkyl-(C


3


-C


8


)-cycloalkyl, (C


2-


-C


6


)-alkenyl-(C


3


-C


8


)-cycloalkyl, (C


2


-C


6


)-alkynyl-(C


3


-C


8


)-cycloalkyl, (C


1


-C


6


)-alkyl-(C


4


-C


8


)-cycloalkenyl, (C


2


-C


6


)-alkenyl-(C


4


-C


8


)-cycloalkenyl,




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




halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C


1


-C


6


)-alkoxy, (C


2


-C


6


)-alkenyloxy, (C


2


-C


6


)-alkynyloxy, (C


1


-C


6


)-haloalkyloxy, (C


2


-C


6


)-haloalkenyloxy, (C


2


-C


6


)-haloalkynyloxy, (C


3


-C


8


)-cycloalkoxy, (C


4


-C


8


)-cycloalkenyloxy, (C


3


-C


8


)-halocycloalkoxy, (C


4


-C


8


)-halocycloalkenyloxy, (C


3


-C


8


)-cycloalkyl-(C


1


-C


4


)-alkoxy, (C


4


-C


6


)-cycloalkenyl-(C


1


-C


4


)-alkoxy, (C


3


-C


8


)-cycloalkyl-(C


2


-C


4


)-alkenyloxy, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkenyloxy, (C


1


-C


6


)-alkyl-(C


3


-C


8


)-cycloalkoxy, (C


2


-C


6


)-alkenyl-(C


3


-C


8


)-cycloalkoxy, (C


2


-C


6


)-alkynyl-(C


3


-C


8


)-cycloalkoxy, (C


1


-C


6


)-alkyl-(C


4


-C


8


)-cycloalkenyloxy, (C


2


-C


6


)-alkenyl-(C


4


-C


8


)-cycloalkenyloxy, (C


1


-C


4


)-alkoxy-(C


1


-C


6


)-alkoxy, (C


1


-C


4


)-alkoxy-(C


2


-C


6


)-alkenyloxy, carbamoyl, (C


1


-C


6


)-mono- or dialkylcarbamoyl, (C


1


-C


6


)-mono- or dihaloalkylcarbamoyl, (C


3


-C


8


)-mono- or dicycloalkylcarbamoyl, (C


1


-C


6


)-alkoxycarbonyl, (C


3


-C


8


)-cycloalkoxycarbonyl, (C


1


-C


6


)-alkanoyloxy, (C


3


-C


8


)-cycloalkanoyloxy, (C


1


-C


6


)-haloalkoxycarbonyl, (C


1


-C


6


)-haloalkanoyloxy, (C


1


-C


6


)-alkaneamido, (C


1


-C


6


)-haloalkaneamido, (C


2


-C


6


)-alkeneamido, (C


3


-C


8


)-cycloalkaneamido, (C


3


-C


8


)-cycloalkyl-(C


1


-C


4


)-alkaneamido, (C


1


-C


6


)-alkylthio, (C


2


-C


6


)-alkenylthio, (C


2


-C


6


)-alkynylthio, (C


1


-C


6


)-haloalkylthio, (C


2


-C


6


)-haloalkenylthio, (C


2


-C


6


)-haloalkynylthio, (C


3


-C


8


)-cycloalkylthio, (C


4


-C


8


)-cycloalkenylthio, (C


3


-C


8


)-halocycloalkylthio, (C


4


-C


8


)-halocycloalkenylthio, (C


3


-C


8


)-cycloalkyl-(C


1


-C


4


)-alkylthio, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkylthio, (C


3


-C


8


)-cycloalkyl-(C


2


-C


4


)-alkenylthio, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkenylthio, (C


1


-C


6


)-alkyl-(C


3


-C


8


)-cycloalkylthio, (C


2


-C


6


)-alkenyl-(C


3


-C


8


)-cycloalkylthio, (C


2


-C


6


)-alkynyl-(C


3


-C


8


)-cycloalkylthio, (C


1


-C


6


)-alkyl-(C


4


-C


8


)-cycloalkenylthio, (C


2


-C


6


)-alkenyl-(C


4


-C


8


)-cycloalkenylthio, (C


1


-C


6


)-alkylsulfinyl, (C


2


-C


6


)-alkenylsulfinyl, (C


2


-C


6


)-alkynylsulfinyl, (C


1


-C


6


)-haloalkylsulfinyl, (C


2


-C


6


)-haloalkenylsulfinyl, (C


2


-C


6


)-haloalkynylsulfinyl, (C


3


-C


8


)-cycloalkylsulfinyl, (C


4


-C


8


)-cycloalkenylsulfinyl, (C


3


-C


8


)-halocycloalksulfinyl, (C


4


-C


8


)-halocycloalkenylsulfinyl, (C


3


-C


8


)-cycloalkyl-(C


1


-C


4


)-alkylsulfinyl, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkylsulfinyl, (C


3


-C


8


)-cycloalkyl-(C


2


-C


4


)-alkenylsulfinyl, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkenylsulfinyl, (C


1


-C


6


)-alkyl-(C


3


-C


8


)-cycloalkylsulfinyl, (C


2


-C


6


)-alkenyl-(C


3


-C


8


)-cycloalkylsulfinyl, (C


2


-C


6


)-alkynyl-(C


3


-C


8


)-cycloalkylsulfinyl, (C


1


-C


6


)-alkyl-(C


4


-C


8


)-cycloalkenyisulfinyl, (C


2


-C


6


)-alkenyl-(C


4


-C


8


)-cycloalkenyisulfinyl, (C


1


-C


6


)-alkylsulfonyl, (C


2


-C


6


)-alkenylsulfonyl, (C


2


-C


6


)-alkynylsulfonyl, (C


1


-C


6


)-haloalkylsulfonyl, (C


2


-C


6


)-haloalkenylsulfonyl, (C


2


-C


6


)-haloalkynylsulfonyl, (C


3


-C


8


)-cycloalkylsulfonyl, (C


4


-C


8


)-cycloalkenylsulfonyl, (C


3


-C


8


)-halocycloalkylsulfonyl, (C


4


-C


8


)-halocycloalkenylsulfonyl, (C


3


-C


8


)-cycloalkyl-(C


1


-C


4


)-alkylsulfonyl, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkylsulfonyl, (C


3


-C


8


)-cycloalkyl-(C


2


-C


4


)-alkenylsulfonyl, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkenylsulfonyl, (C


1


-C


6


)-alkyl-(C


3


-C


8


)-cycloalkylsulfonyl, (C


2


-C


6


)-alkenyl-(C


3


-C


8


)-cycloalkylsulfonyl, (C


2


-C


6


)-alkynyl-(C


3


-C


8


)-cycloalkylsulfonyl, (C


1


-C


6


)-alkyl-(C


4


-C


8


)-cycloalkenylsulfonyl, (C


2


-C


6


)-alkenyl-(C


4


-C


8


)-cycloalkenyisulfonyl, (C


1


-C


6


)-alkylamino, (C


2


-C


6


)-alkenylamino, (C


2


-C


6


)-alkynylamino, (C


1


-C


6


)-haloalkylamino, (C


2


-C


6


)-haloalkenylamino, (C


2


-C


6


)-haloalkynylamino, (C


3


-C


8


)-cycloalkylamino, (C


4


-C


8


)-cycloalkenylamino, (C


3


-C


8


)-halocycloalkamino, (C


4


-C


8


)-halocycloalkenylamino, (C


3


-C


8


)-cycloalkyl-(C


1


-C


4


)-alkylamino, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkylamino, (C


3


-C


8


)-cycloalkyl-(C


2


-C


4


)-alkenylamino, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkenylamino, (C


1


-C


6


)-alkyl-(C


3


-C


8


)-cycloalkylamino, (C


2


-C


6


)-alkenyl-(C


3


-C


8


)-cycloalkylamino, (C


2


-C


6


)-alkynyl-(C


3


-C


8


)-cycloalkylamino, (C


1


-C


6


)-alkyl-(C


4


-C


8


)-cycloalkenylamino, (C


2


-C


6


)-alkenyl-(C


4


-C


8


)-cycloalkenylamino, (C


1


-C


6


)-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, arylcarbamoyl, aroyl, aroyloxy, aryloxycarbonyl, aryl-(C


1


-C


4


)-alkoxy, aryl-(C


2


-C


4


)-alkenyloxy, aryl-(C


1


-C


4


)-alkylthio, aryl-(C


2


-C


4


)-alkenylthio, aryl-(C


1


-C


4


)-alkylamino, aryl-(C


2


-C


4


)-alkenylamino, aryl-(C


1


-C


6


)-dialkylsilyl, diaryl-(C


1


-C


6


)-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl,




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




halogen, cyano, nitro, amino, hydroxyl, thio, (C


1


-C


4


)-alkyl, (C


1


-C


4


)-haloalkyl, (C


1


-C


4


)-alkoxy, (C


1


-C


4


)-haloalkoxy, (C


1


-C


4


)-alkylthio, (C


1


-C


4


)-haloalkylthio, (C


1


-C


4


)-alkylamino, (C


1


-C


4


)-haloalkylamino, formyl and (C


1


-C


4


)-alkanoyl;




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




halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C


1


-C


6


)-alkoxy, (C


2


-C


6


)-alkenyloxy, (C


2


-C


6


)-alkynyloxy, (C


1


-C


6


)-haloalkyloxy, (C


2


-C


6


)-haloalkenyloxy, (C


2


-C


6


)-haloalkynyloxy, (C


3


-C


8


)-cycloalkoxy, (C


4


-C


8


)-cycloalkenyloxy, (C


3


-C


8


)-halocycloalkoxy, (C


4


-C


8


)-halocycloalkenyloxy, carbamoyl, (C


1


-C


6


)-mono- or dialkylcarbamoyl, (C


1


-C


6


)-alkoxycarbonyl, (C


1


-C


6


)-alkanoyloxy, (C


1


-C


6


)-mono- or dihaloalkylcarbamoyl, (C


1


-C


6


)-haloalkoxycarbonyl, (C


1


-C


6


)-haloalkanoyloxy, (C


1


-C


6


)-alkaneamido, (C


1


-C


6


)-haloalkaneamido, (C


2


-C


6


)-alkeneamido, (C


1


-C


6


)-alkylthio, (C


2


-C


6


)-alkenylthio, (C


2


-C


6


)-alkynylthio, (C


1


-C


6


)-haloalkylthio, (C


2


-C


6


)-haloalkenylthic, (C


2


-C


6


)-haloalkynylthio, (C


3


-C


8


)-cycloalkylthio, (C


4


-C


8


)-cycloalkenylthio, (C


3


-C


8


)-halocycloalkthio, (C


3


-C


8


)-halocycloalkenylthio, (C


1


-C


6


)-alkylsulfinyl, (C


2


-C


6


)-alkenylsulfinyl, (C


2


-C


6


)-alkynylsulfinyl, (C


1


-C


6


)-haloalkylsulfinyl, (C


2


-C


6


)-haloalkenylsulfinyl, (C


2


-C


6


)-haloalkynylsulfinyl, (C


3


-C


8


)-cycloalkylsulfinyl, (C


4


-C


8


)-cycloalkenylsulfinyl, (C


3


-C


8


)-halocycloalksulfinyl, (C


4


-C


8


)-halocycloalkenylsulfinyl, (C


1


-C


6


)-alkylsulfonyl, (C


2


-C


6


)-alkenylsulfonyl, (C


2


-C


6


)-alkynylsulfonyl, (C


1


-C


6


)-haloalkylsulfonyl, (C


2


-C


6


)-haloalkenylsulfonyl, (C


2


-C


6


)-haloalkynylsulfonyl, (C


3


-C


8


)-cycloalkylsulfonyl, (C


4


-C


8


)-cycloalkenylsulfonyl, (C


3


-C


8


)-halocycloalksulfonyl, (C


4


-C


8


)-halocycloalkenylsulfonyl, (C


1


-C


6


)-alkylamino, (C


2


-C


6


)-alkenylamino, (C


2


-C


6


)-alkynylamino, (C


1


-C


6


)-haloalkylamino, (C


2


-C


6


)-haloalkenylamino, (C


2


-C


6


)-haloalkynylamino, (C


3


-C


8


)-cycloalkylamino, (C


4


-C


8


)-cycloalkenylamino, (C


3


-C


8


)-halocycloalkamino and (C


4


-C


8


)-halocycloalkenylamino,




—C(═W)R


11


, OR


11


or NR


11




2


;




R


9


is (C


1


-C


6


)-alkyl, (C


2


-C


6


)-alkenyl, (C


2


-C


6


)-alkynyl, (C


3


-C


8


)-cycloalkyl, (C


4


-C


8


)-cycloalkenyl, (C


3


-C


8


)-cycloalkyl-(C


1


-C


4


)-alkyl, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkyl, (C


3


-C


8


)-cycloalkyl-(C


2


-C


4


)-alkenyl, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkenyl,




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




halogen, cyano, (C


1


-C


6


)-alkoxy, (C


2


-C


6


)-alkenyloxy, (C


2


-C


6


)-alkynyloxy and (C


1


-C


6


)-haloalkyloxy;




R


10


is hydrogen,




(C


1


-C


6


)-alkyl, (C


2


-C


6


)-alkenyl, (C


2


-C


6


)-alkynyl, (C


3


-C


8


)-cycloalkyl, (C


4


-C


8


)-cycloalkenyl, (C


3


-C


8


)-cycloalkyl-(C


1


-C


4


)-alkyl, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkyl, (C


3


-C


8


)-cycloalkyl-(C


2


-C


4


)-alkenyl, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkenyl, (C


1


-C


6


)-alkyl-(C


3


-C


8


)-cycloalkyl, (C


2


-C


6


)-alkenyl-(C


3


-C


8


)-cycloalkyl, (C


2


-C


6


)-alkynyl-(C


3


-C


8


)-cycloalkyl, (C


1


-C


6


)-alkyl-(C


4


-C


8


)-cycloalkenyl, (C


2


-C


6


)-alkenyl-(C


4


-C


8


)-cycloalkenyl,




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




halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C


1


-C


6


)-alkoxy, (C


2


-C


6


)-alkenyloxy, (C


2


-C


6


)-alkynyloxy, (C


1


-C


6


)-haloalkyloxy, (C


2


-C


6


)-haloalkenyloxy, (C


2


-C


6


)-haloalkynyloxy, (C


3


-C


8


)-cycloalkoxy, (C


4


-C


8


)-cycloalkenyloxy, (C


3


-C


8


)-halocycloalkoxy, (C


4


-C


8


)-halocycloalkenyloxy, (C


3


-C


8


)-cycloalkyl-(C


1


-C


4


)-alkoxy, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkoxy, (C


3


-C


8


)-cycloalkyl-(C


2


-C


4


)-alkenyloxy, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkenyloxy, (C


1


-C


6


)-alkyl-(C


3


-C


8


)-cycloalkoxy, (C


2


-C


6


)-alkenyl-(C


3


-C


8


)-cycloalkoxy, (C


2


-C


6


)-alkynyl-(C


3


-C


8


)-cycloalkoxy, (C


1


-C


6


)-alkyl-(C


4


-C


8


)-cycloalkenyloxy, (C


2


-C


6


)-alkenyl-(C


4


-C


8


)-cycloalkenyloxy, (C


1


-C


4


)-alkoxy-(C


1


-C


6


)-alkoxy, (C


1


-C


4


)-alkoxy-(C


2


-C


6


)-alkenyloxy, carbamoyl, (C


1


-C


6


)-mono- or dialkylcarbamoyl, (C


1


-C


6


)-mono- or dihaloalkylcarbamoyl, (C


3


-C


8


)-mono- or dicycloalkylcarbamoyl, (C


1


-C


6


)-alkoxycarbonyl, (C


3


-C


8


)-cycloalkoxycarbonyl, (C


1


-C


6


)-alkanoyloxy, (C


3


-C


8


)-cycloalkanoyloxy, (C


1


-C


6


)-haloalkoxycarbonyl, (C


1


-C


6


)-haloalkanoyloxy, (C


1


-C


6


)-alkaneamido, (C


1


-C


6


)-haloalkaneamido, (C


2


-C


6


)-alkeneamido, (C


3


-C


8


)-cycloalkaneamido, (C


3


-C


8


)-cycloalkyl-(C


1


-C


4


)-alkaneamido, (C


1


-C


6


)-alkylthio, (C


2


-C


6


)-alkenylthio, (C


2


-C


6


)-alkynylthio, (C


1


-C


6


)-haloalkylthio, (C


2


-C


6


)-haloalkenylthio, (C


2


-C


6


)-haloalkynylthio, (C


3


-C


8


)-cycloalkylthio, (C


4


-C


8


)-cycloalkenylthio, (C


3


-C


8


)-halocycloalkthio, (C


4


-C


8


)-halocycloalkenylthio, (C


3


-C


8


)-cycloalkyl-(C


1


-C


4


)-alkylthio, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkylthio, (C


3


-C


8


)-cycloalkyl-(C


2


-C


4


)-alkenylthio, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkenylthio, (C


1


-C


6


)-alkyl-(C


3


-C


8


)-cycloalkylthio, (C


2


-C


6


)-alkenyl-(C


3


-C


8


)-cycloalkylthio, (C


2


-C


6


)-alkynyl-(C


3


-C


8


)-cycloalkylthio, (C


1


-C


6


)-alkyl-(C


4


-C


8


)-cycloalkenylthio, (C


2


-C


6


)-alkenyl-(C


4


-C


8


)-cycloalkenylthio, (C


1


-C


6


)-alkylsulfinyl, (C


2


-C


6


)-alkenylsulfinyl, (C


2


-C


6


)-alkynylsulfinyl, (C


1


-C


6


)-haloalkylsulfinyl, (C


2


-C


6


)-haloalkenylsulfinyl, (C


2


-C


6


)-haloalkynylsulfinyl, (C


3


-C


8


)-cycloalkylsulfinyl, (C


4


-C


8


)-cycloalkenylsulfinyl, (C


3


-C


8


)-halocycloalksulfinyl, (C


4


-C


8


)-halocycloalkenylsulfinyl, (C


3


-C


8


)-cycloalkyl-(C


1


-C


4


)-alkylsulfinyl, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkylsulfinyl, (C


3


-C


8


)-cycloalkyl-(C


2


-C


4


)-alkenylsulfinyl, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkenylsulfinyl, (C


1


-C


6


)-alkyl-(C


3


-C


8


)-cycloalkylsulfinyl, (C


2


-C


6


)-alkenyl-(C


3


-C


8


)-cycloalkylsulfinyl, (C


2


-C


6


)-alkynyl-(C


3


-C


8


)-cycloalkylsulfinyl, (C


1


-C


6


)-alkyl-(C


4


-C


8


)-cycloalkenylsulfinyl, (C


2


-C


6


)-alkenyl-(C


4


-C


8


)-cycloalkenylsulfinyl, (C


1


-C


6


)-alkylsulfonyl, (C


2


-C


6


)-alkenylsulfonyl, (C


2


-C


6


)-alkynylsulfonyl, (C


1


-C


6


)-haloalkylsulfonyl, (C


2


-C


6


)-haloalkenylsulfonyl, (C


2


-C


6


)-haloalkynylsulfonyl, (C


3


-C


8


)-cycloalkylsulfonyl, (C


4


-C


8


)-cycloalkenylsulfonyl, (C


3


-C


8


)-halocycloalksulfonyl, (C


4


-C


8


)-halocycloalkenylsulfonyl, (C


3


-C


8


)-cycloalkyl-(C


1


-C


4


)-alkylsulfonyl, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkylsulfonyl, (C


3


-C


8


)-cycloalkyl-(C


2


-C


4


)-alkenylsulfonyl, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkenylsulfonyl, (C


1


-C


6


)-alkyl-(C


3


-C


8


)-cycloalkylsulfonyl, (C


2


-C


6


)-alkenyl-(C


3


-C


8


)-cycloalkylsulfonyl, (C


2


-C


6


)-alkynyl-(C


3


-C


8


)-cycloalkylsulfonyl, (C


1


-C


6


)-alkyl-(C


4


-C


8


)-cycloalkenylsulfonyl, (C


2


-C


6


)-alkenyl-(C


4


-C


8


)-cycloalkenylsulfonyl, (C


1


-C


6


)-alkylamino, (C


2


-C


6


)-alkenylamino, (C


2


-C


6


)-alkynylamino, (C


1


-C


6


)-haloalkylamino, (C


2


-C


6


)-haloalkenylamino, (C


2


-C


6


)-haloalkynylamino, (C


3


-C


8


)-cycloalkylamino, (C


4


-C


8


)-cycloalkenylamino, (C


3


-C


8


)-halocycloalkamino, (C


4


-C


8


)-halocycloalkenylamino, (C


3


-C


8


)-cycloalkyl-(C


1


-C


4


)-alkylamino, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkylamino, (C


3


-C


8


)-cycloalkyl-(C


2


-C


4


)-alkenylamino, (C


4


-C


8


)-cycloalkenyl-(C


1


-C


4


)-alkenylamino, (C


1


-C


6


)-alkyl-(C


3


-C


8


)-cycloalkylamino, (C


2


-C


6


)-alkenyl-(C


3


-C


8


)-cycloalkylamino, (C


2


-C


6


)-alkynyl-(C


3


-C


8


)-cycloalkylamino, (C


1


-C


6


)-alkyl-(C


4


-C


8


)-cycloalkenylamino, (C


2


-C


6


)-alkenyl-(C


4


-C


8


)-cycloalkenylamino, (C


1


-C


6


)-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, aryl-(C


1


-C


4


)-alkoxy, aryl-(C


2


-C


4


)-alkenyloxy, aryl-(C


1


-C


4


)-alkylthio, aryl-(C


2


-C


4


)-alkenylthio, aryl-(C


1


-C


4


)-alkylamino, aryl-(C


2


-C


4


)-alkenylamino, aryl-(C


1


-C


6


)-dialkylsilyl, diaryl-(C


1


-C


6


)-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl,




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




halogen, cyano, nitro, amino, hydroxyl, thio, (C


1


-C


4


)-alkyl, (C


1


-C


4


)-haloalkyl, (C


3


-C


8


)-cycloalkyl, (C


1


-C


4


)-alkoxy, (C


1


-C


4


)-haloalkoxy, (C


1


-C


4


)-alkylthio, (C


1


-C


4


)-haloalkylthio, (C


1


-C


4


)-alkylamino, (C


1


-C


4


)-haloalkylamino, formyl and (C


1


-C


4


)-alkanoyl;




aryl, 5- or 6-membered heteroaromatic,




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




halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C


1


-C


6


)-alkoxy, (C


2


-C


6


)-alkenyloxy, (C


2


-C


6


)-alkynyloxy, (C


1


-C


6


)-haloalkyloxy, (C


2


-C


6


)-haloalkenyloxy, (C


2


-C


6


)-haloalkynyloxy, (C


3


-C


8


)-cycloalkoxy, (C


4


-C


8


)-cycloalkenyloxy, (C


3


-C


8


)-halocycloalkoxy, (C


4


-C


8


)-halocycloalkenyloxy, carbamoyl, (C


1


-C


6


)-mono- or dialkylcarbamoyl, (C


1


-C


6


)-alkoxycarbonyl, (C


1


-C


6


)-alkanoyloxy, (C


1


-C


6


)-mono- or dihaloalkylcarbamoyl, (C


1


-C


6


)-haloalkoxycarbonyl, (C


1


-C


6


)-haloalkanoyloxy, (C


1


-C


6


)-alkaneamido, (C


1


-C


6


)-haloalkaneamido, (C


2


-C


6


)-alkeneamido, (C


1


-C


6


)-alkylthio, (C


2


-C


6


)-alkenylthio, (C


2


-C


6


)-alkynylthio, (C


1


-C


6


)-haloalkylthio, (C


2


-C


6


)-haloalkenylthio, (C


2


-C


6


)-haloalkynylthio, (C


3


-C


8


)cycloalkylthio, (C


4


-C


8


)-cycloalkenylthio, (C


3


-C


8


)-halocycloalkthio, (C


4


-C


8


)-halocycloalkenylthio, (C


1


-C


6


)-alkylsulfinyl, (C


2


-C


6


)-alkenylsulfinyl, (C


2


-C


6


)-alkynylsulfinyl, (C


1


-C


6


)-haloalkylsulfinyl, (C


2


-C


6


)-haloalkenylsulfinyl, (C


2


-C


6


)-haloalkynylsulfinyl, (C


3


-C


8


)-cycloalkylsulfinyl, (C


4


-C


8


)-cycloalkenylsulfinyl, (C


3


-C


8


)-halocycloalksulfinyl, (C


4


-C


8


)-halocycloalkenylsulfinyl, (C


1


-C


6


)-alkylsulfonyl, (C


2


-C


6


)-alkenylsulfonyl, (C


2


-C


6


)-alkynylsulfonyl, (C


1


-C


6


)-haloalkylsulfonyl, (C


2


-C


6


)-haloalkenylsulfonyl, (C


2


-C


6


)-haloalkynylsulfonyl, (C


3


-C


8


)-cycloalkylsulfonyl, (C


4


-C


8


)-cycloalkenylsulfonyl, (C


3


-C


8


)-halocycloalksulfonyl, (C


4


-C


8


)-halocycloalkenylsulfonyl, (C


1


-C


6


)-alkylamino, (C


2


-C


6


)-alkenylamino, (C


2


-C


6


)-alkynylamino, (C


1


-C


6


)-haloalkylamino, (C


2


-C


6


)-haloalkenylamino, (C


2


-C


6


)-haloalkynylamino, (C


3


-C


8


)cycloalkylamino, (C


4


-C


8


)-cycloalkenylamino, (C


3


-C


8


)-halocycloalkylamino and (C


4


-C


8


)-halocycloalkenylamino;




R


11


is (C


1


-C


10


)-alkyl, haloalkyl, aryl, which is optionally substituted by one or more radicals from the group halogen, cyano, nitro, (C


1


-C


4


)-alkoxy, (C


1


-C


4


)-alkyl, amino, (C


1


-C


4


)-monoalkylamino and (C


1


-C


4


)-dialkylamino;




NR


10




2


, OR


10


or SR


10


.




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




The term “(C


1


-C


4


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


1


-C


6


)-alkyl” includes the abovementioned alkyl radicals, and, for example, the pentyl, 2-methylbutyl, 1,1-dimethylpropyl, hexyl radical. The term “(C


1


-C


10


)-alkyl” is to be understood as the abovementioned alkyl radicals, and, for example, the nonyl, 1-decyl or 2-decyl radical and the term “(C


1


-C


20


)-alkyl” is to be understood as the abovementioned alkyl radicals, and, for example, the undecyl, dodecyl, pentadecyl or eicosyl radical.




“(C


1


-C


4


)-Haloalkyl” is to be understood as an alkyl group mentioned under the term “(C


1


-C


4


)-alkyl” in which one or more hydrogen atoms are replaced by the same number of identical or different halogen atoms, preferably by fluorine or chlorine, such as the trifluoromethyl, the 1-fluoroethyl, the 2,2,2-trifluoroethyl, the chloromethyl, fluoromethyl, the difluoromethyl and the 1,1,2,2-tetrafluoroethyl group.




“(C


1


-C


4


)-Alkoxy” is to be understood as an alkoxy group whose hydrocarbon radical has the meaning given under the term “(C


1


-C


4


)-alkyl”. Alkoxy groups embracing a greater range of carbon atoms are to be understood correspondingly.




The terms “alkenyl” and “alkynyl” having a prefix stating the range of carbon atoms denote a straight-chain or branched hydrocarbon radical having a number of carbon atoms corresponding to the range stated which comprises at least one multiple bond which may be in any position of the unsaturated radical in question. “(C


2


-C


4


)-Alkenyl” is thus, for example, the vinyl, allyl, 2-methyl-2-propene or 2-butenyl group; “(C


2


-C


6


)-alkenyl” denotes the abovementioned radicals and, for example, the pentenyl, 2-methylpentenyl or the hexenyl group. The term “(C


2


-C


20


)-alkenyl” is to be understood as the abovementioned radicals and, for example, the 2-decenyl or the 2-eicosenyl group. “(C


2


-C


4


)-Alkynyl” is, for example, the ethynyl, propargyl, 2-methyl-2-propyne or 2-butynyl group. “(C


2


-C


6


)-Alkynyl” is to be understood as the abovementioned radicals and, for example, the 2-pentynyl- or the 2-hexynyl group and “(C


2


-C


20


)-alkynyl” is to be understood as the abovementioned radicals and, for example, the 2-octynyl or the 2-decynyl group.




“(C


3


-C


8


)-Cycloalkyl” denotes monocyclic alkyl radicals, such as the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radical and bicyclic alkyl radicals, such as the norbomyl radical.




The term “(C


3


-C


8


)-cycloalkyl-(C


1


-C


4


)-alkyl” is to be understood as, for example, the cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylbutyl radical, and the term “(C


1


-C


6


)-alkyl-(C


3


-C


8


)-cycloalkyl is to be understood as, for example, the 1-methylcyclopropyl, 1-methylcyclopentyl, 1-methylcyclohexyl, 3-hexylcyclobutyl and 4-tert-butyl-cyclohexyl radical.




“(C


1


-C


4


)-Alkoxy-(C


1


-C


6


)-alkyloxy” is an alkoxy group as defined above which is substituted by a further alkoxy group, such as, for example, 1-ethoxyethoxy.




“(C


3


-C


8


)-Cycloalkoxy” or “(C


3


-C


8


)-cycloalkylthio” is to be understood as one of the abovementioned (C


3


-C


8


)-cycloalkyl radicals which is linked via an oxygen or sulfur atom.




“(C


3


-C


8


)-Cycloalkyl-(C


1


-C


6


)-alkoxy” is, for example, the cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclohexylethoxy or the cyclohexylbutoxy group;




The term “(C


1


-C


4


)-alkyl-(C


3


-C


8


)-cycloalkoxy” is, for example, the methylcyclopropyloxy, methylcyclobutyloxy or the butylcyclohexyloxy group.




“(C


1


-C


6


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


1


-C


6


)-alkyl”.




Correspondingly, “(C


1


-C


6


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


1


-C


6


)-alkylsulfonyl” is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfonyl group.




“(C


1


-C


6


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




The term “(C


1


-C


6


)-mono- or dialkylcarbamoyl” is a carbamoyl group having one or two hydrocarbon radicals which have the meaning given under the term “(C


1


-C


6


-alkyl)” and which, in the case of two hydrocarbon radicals, may be identical or different.




Correspondingly, “(C


1


-C


6


)-dihaloalkylcarbamoyl” is a carbamoyl group which carries two (C


1


-C


6


)-haloalkyl radicals in accordance with the above definition or one (C


1


-C


6


)-haloalkyl radical and one (C


1


-C


6


)-alkyl radical in accordance with the above definition.




“(C


1


-C


6


)-Alkanoyl” is, for example, the acetyl, propionyl, butyryl or 2-methylbutyryl group.




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




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




“Aryl-(C


1


-C


4


)-alkoxy” is an aryl radical which is attached via a (C


1


-C


4


)-alkoxy group, for example the benzyloxy, phenylethoxy, phenylbutoxy or naphthylmethoxy radical.




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




“Aryl-(C


1


-C


4


)-alkylthio” is an aryl radical which is attached via an alkylthio radical, for example the benzylthio, naphthylmethylthio or the phenylethylthio radical.




The term “(C


1


-C


6


)-trialkylsilyl” denotes a silicon atom which carries three identical or different alkyl radicals in accordance with the above definition. Correspondingly “aryl-(C


1


-C


6


)-dialkylsilyl” is a silicon atom which carries one aryl radical and two identical or different radicals in accordance with the above definition, “diaryl-(C


1


-C


6


)-alkylsilyl” is a silicon atom which carries one alkyl radical and two identical or different aryl radicals in accordance with the above definition, and “triarylsilyl” is a silicon atom which carries three identical or different aryl radicals in accordance with the above definition.




In cases where two or more radicals R


10


are present in a substituent, such as, for example, in —C(═W)NR


10




2


, these radicals may be identical or different.




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




Y is C


1


-C


6


-alkyl which is mono- or polysubstituted by chlorine and/or fluorine;




m is zero;




Q is a 5-membered heterocyclic group











in which




a) X


2


=NR


a


and X


3


=CR


b


R


1


or




b) X


2


=CR


a


R


2


and X


3


=CR


b


R


3


or




c) X


2


=CR


4


R


5


and X


3


=CR


6


R


7


;




R


a


and R


b


together are a bond;




R


1


, R


2


, R


3


, R


4


and R


6


are each independently of one another hydrogen, halogen, C


1


-C


12


-alkyl, C


3


-C


8


-cycloalkyl, C


2


-C


8


-alkenyl, C


2


-C


8


-alkynyl, where the four last-mentioned hydrocarbon radicals are optionally mono- or polysubstituted by identical or different radicals from a group A1 consisting of C


1


-C


6


-alkylcarbonyl, C


1


-C


6


-alkylaminocarbonyl, C


1


-C


6


-alkoxy, C


1


-C


6


-alkylthio, C


1


-C


6


-alkylamino, C


1


-C


6


-alkylcarbonylamino, C


1


-C


6


-alkylsulfonylamino, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino, where the eleven first-mentioned radicals of group A1 are each optionally mono- or polysubstituted by identical or different radicals from a group B1 consisting of halogen, cyano, C


1


-C


3


-alkoxy and phenyl which is optionally mono- or polysubstituted by one or more halogen atoms and where the three last-mentioned radicals of group A1 are each optionally mono- or polysubstituted by identical or different radicals from a group B2 consisting of halogen, cyano, nitro, C


1


-C


3


-alkyl and C


1


-C


3


-alkoxy, or are C


1


-C


6


-alkylcarbonyl, C


1


-C


6


-alkylaminocarbonyl, C


1


-C


6


-alkoxycarbonyl, phenyl, pyridyl, furyl, thienyl, pyrryl, where the eight last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from group B1, or are OR


10


, SR


10


or N(R


10


)


2


;




R


5


and R


7


are each independently of one another hydrogen, halogen, C


1


-C


12


-alkyl, C


3


-C


8


-cycloalkyl, C


2


-C


8


-alkenyl, C


2


-C


8


-alkynyl, where the four last-mentioned hydrocarbon radicals are optionally mono- or polysubstituted by identical or different radicals from a group A2 consisting of C


1


-C


6


-alkylcarbonyl, C


1


-C


6


-alkylaminocarbonyl, C


1


-C


6


-alkoxy, C


1


-C


6


-alkylthio, C


1


-C


6


-alkylamino, C


1


-C


6


-alkylcarbonylamino, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino, where the ten first-mentioned radicals of group A2 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A2 are each optionally mono- or polysubstituted by identical or different radicals from the group B2, or are C


1


-C


6


-alkylcarbonyl, C


1


-C


6


-alkylaminocarbonyl, C


1


-C


6


-alkoxycarbonyl, phenyl, pyridyl, furyl, thienyl, pyrryl, where the eight last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from the group B1, or are OR


10


, SR


10


or N(R


10


)


2


;




R


10


is hydrogen, benzyl, C


1


-C


6


-alkyl, C


1


-C


6


-cycloalkyl, C


2


-C


6


-alkenyl, C


2


-C


6


-alkynyl, phenyl, C


1


-C


6


-alkylcarbonyl or C


1


-C


6


-alkylsulfonyl, where the eight last-mentioned radicals are optionally mono- or polysubstituted by identical or different halogen atoms.




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




Y is trifluoromethyl;




R


1


, R


2


, R


3


, R


4


and R


6


are each independently of one another halogen, C


1


-C


12


-alkyl, C


2


-C


12


-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A3 consisting of C


1


-C


4


-alkylcarbonyl, C


1


-C


4


-alkylaminocarbonyl, C


1


-C


4


-alkoxy, C


1


-C


4


-alkylthio, C


1


-C


4


-alkylamino, C


1


-C


4


-alkylcarbonylamino, C


1


-C


4


-alkylsulfonylamino, phenyl, furyl, pyrryl, thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the eleven first-mentioned radicals of group A3 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A3 are each optionally mono- or polysubstituted by identical or different radicals from the group B2, or are OR


10


, SR


10


or N(R


10


)


2


;




R


5


and R


7


are each independently of one another halogen, C


1


-C


12


-alkyl, C


2


-C


12


-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A4 consisting of C


1


-C


4


-alkylcarbonyl, C


1


-C


4


-alkylaminocarbonyl, C


1


-C


4


-alkoxy, C


1


-C


4


-alkylthio, C


1


-C


4


-alkylamino, C


1


-C


4


-alkylcarbonylamino, phenyl, furyl, pyrryl, thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the ten first-mentioned radicals of group A4 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A4 are each optionally mono- or polysubstituted by identical or different radicals from the group B2, or are OR


10


, SR


10


or N(R


10


)


2


;




R


10


is hydrogen, C


1


-C


6


-alkyl, C


2


-C


6


-alkenyl, C


2


-C


6


-alkynyl, phenyl, C


1


-C


4


-alkylcarbonyl or C


1


-C


4


-alkylsulfonyl, where the six last-mentioned radicals are optionally mono- or polysubstituted by identical or different halogen atoms.




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




R


1


, R


2


, R


3


, R


4


and R


6


are each independently of one another C


1


-C


10


-alkyl, C


2


-C


10


-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A5 consisting of C


1


-C


4


-alkylcarbonyl, C


1


-C


4


-alkylaminocarbonyl, C


1


-C


4


-alkoxy, C


1


-C


4


-alkylthio, C


1


-C


4


-alkylamino, C


1


-C


4


-alkylcarbonylamino, C


1


-C


4


-alkylsulfonylamino, phenyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the eight first-mentioned radicals of group A5 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A5 are each optionally mono- or polysubstituted by identical or different radicals from the group B2;




R


5


and R


7


are each independently of one another C


1


-C


10


-alkyl, C


2


-C


10


-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A6 consisting of C


1


-C


4


-alkylcarbonyl, C


1


-C


4


-alkylaminocarbonyl, C


1


-C


4


-alkoxy, C


1


-C


4


-alkylthio, C


1


-C


4


-alkylamino, C


1


-C


4


-alkylcarbonylamino, phenyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the seven first-mentioned radicals of group A6 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A6 are each optionally mono- or polysubstituted by identical or different radicals from the group B2.




Depending on the nature of the substituents defined above, the compounds of the formula (I) have acidic or basic properties and can form salts. If the compounds of the formula (I) carry, for example, groups such as hydroxyl, carboxyl and other groups inducing acidic properties, these compounds can be reacted with bases to give salts. Suitable bases are, for example, hydroxides, carbonates, bicarbonates of the alkali metals and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, further ammonia, primary, secondary and tertiary amines having (C


1


-C


4


)-alkyl radicals and also mono-, di- and trialkanolamines of (C


1


-C


4


)-alkanols. If the compounds of the formula (I) carry, for example, groups such as amino, alkylamino and other groups inducing basic properties, these compounds can be reacted with acids to give salts. Suitable acids are, for example, mineral acids, such as hydrochloric acid, sulfuric acid and phosphoric acid, organic acids, such as acetic acid, oxalic acid and acidic salts, such as NaHSO


4


and KHSO


4


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




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




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




To prepare compounds of the formula (I) in which




a) X


1


=W, X


2


=NR


a


, X


3


=CR


b


R


1






and R


a


, R


b


and R


1


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











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











in which the radical R


1


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




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











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




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




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




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











The compounds of the formula (VII) required as starting materials for this reaction can be prepared by reacting the thioamides of the formula (VII) with dialkylamide dialkyl acetals, of formula (IX), where R


1


is as defined above and R


12


and R


13


are each C


1


-C


4


-alkyl.











To prepare compounds of the formula (I) in which




b) X


1


=NR


a


, X


2


=CR


b


R


1


, X


3


=W




and R


a


, R


b


and R


1


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











To prepare compounds of the formula (I) in which




c) X


1


=V, X


2


=CR


a


R


1


, X


3


=NR


b






and R


a


, R


b


and R


1


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











In the abovementioned case b) where W is oxygen, the compounds of the formula (I) can be prepared by reaction of acids of the formula (II) with hydrazines of the formula (X), in which R


1


is as defined above, using an activating reagent, such as phosphorus oxychloride or phosphorus pentachloride.











It is also possible to react acid hydrazides of the formula (XI) with ortho esters of the formula (XII) where R


1


is as defined above, and R


12


is (C


1


-C


4


)-alkyl.











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




To prepare compounds of the formula (I) in which




d) X


1


=V, X


2


=CR


a


R


2


, X


3


=CR


b


R


3






and R


a


, R


b


and R


3


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











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




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











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











To prepare compounds of the formula (I) in which




e) X


1


=V, X


2


=CR


4


R


5


, X


3


=CR


6


R


7






and R


4


, R


5


, R


6


and R


7


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











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











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











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




For preparing compounds of the formula (I) in which




f) X


1


=NR


a


, X


2


=CR


b


R


1


, X


3


=NR


8






and R


a


, R


b


, R


1


and R


8


are as defined above, hydrazides of the formula (XX)











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











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




Once the group Q has been assembled, for example by condensation, cyclization or cycloaddition reactions, the radicals R


1


to R


9


may be derivatized further, if desired, employing the extensive arsenal of methods of organochemical synthesis.




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




The compounds of the formula (I) (also referred to as “active compounds” hereinbelow) have good plant tolerance, favorable homotherm toxicity and advantageous properties with respect to aquatic organisms and are suitable for controlling animal pests, in particular insects, arachnids (Acarina), helminths and 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.




From the order of the Isopoda, for example,


Oniscus asselus, Armadium vulgar


and


Porcellio scaber.


From the order of the Diplopoda, for example,


Blaniulus guttulatus.


From the order of the Chilopoda, for example,


Geophilus carpophagus


and Scutigera spp. From the order of the Symphyla, for example,


Scutigerella immaculata.


From the order of the Thysanura, for example,


Lepisma saccharina.


From the order of the Collembola, for example,


Onychiurus armatus.


From the order of the Orthoptera, for example,


Blatta orientalis, Periplaneta americana, Leucophaea madeirae, Blatella germanica, Acheta domesticus,


Gryllotalpa spp.,


Locusta migratoria migratorioides, Melanoplus differentialis


and


Schistocerca gregaria.






From the order of the isoptera, for example, Reticulitermes spp. From the order of the Anoplura, for example,


Phylloera vastatrix,


Pemphigus spp.,


Pediculus humanus corporis,


Haematopinus spp. and Linognathus spp.




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


Hercinothrips femoralis, Thrips tabaci


and Frankliniella spp.




From the order of the Heteroptera, for example, Eurygaster spp.,


Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus


and Triatoma spp.




From the order of the Homoptera, for example,


Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum,


Aphis spp.,


Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae,


Myzus spp.,


Phorodon humuli, Rhopalosiphum padi,


Empoasca spp.,


Euscelus bilobatus, Nephotettix cincticeps, Lecanium comi, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae,


Pseudococcus spp. and Psylla spp.




From the order of the Lepidoptera, for example,


Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea,


Lymantria spp.,


Bucculatrix thurberiella, Phyllocnistis citrella,


Agrotis spp., Euxoa spp., Feltia spp.,


Earias insulana,


Heliothis spp.,


Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura,


Spodoptera spp.,


Trichoplusia ni, Carpocapsa pomonella,


Pieris spp., Chilo spp.,


Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana,


Cuaphalocrocis spp. and Manduca spp.




From the order of the Coleoptera, for example,


Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae,


Diabrotica spp.,


Psylloides chrysocephala, Epilachna varivestis,


Atomaria spp.,


Oryzaephilus surinamensis,


Anthonumus spp., Sitophilus spp.,


Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrynchus assimilis, Hypera postica,


Dermestes spp., Trogoderma, Anthrenus spp., Attagenus spp., Lyctus spp.,


Meligethes aeneus,


Ptinus spp.,


Niptus hololeucus, Gibbium psylloides,


Tribolium spp.,


Tenebrio molitor,


Agriotes spp., Conoderus spp.,


Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica


and Lissorhoptus spp.




From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp.,


Monomorium pharaonis


and Vespa spp.




From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp.,


Drosophila melanogaster,


Musca spp., Fannia spp.,


Calliphora erythrocephala,


Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp.,


Bibio hortulanus, Oscinella frit,


Phorbia spp.,


Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae


and


Tipula paludosa.






From the order of the Siphonaptera, for example,


Xenopsylla cheopsis


and Ceratophyllus spp. From the order of the Arachnida, for example,


Scorpio maurus


and


Latrodectus mactans.


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




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




The phytoparasitic nematodes which can be controlled according to the invention include, for example, the root-parasitic soil nematodes, such as, for example, those of the genera Meloidogyne (root gall nematodes, such as


Meloidogyne incognita, Meloidogyne hapla


and


Meloidogyne javanica


), Heterodera and Globodera (cyst-forming nematodes, such as


Globodera rostochiensis, Globodera pallida


and


Heterodera trifolii


) and of the genera Radopholus (such as


Radopholus similis


), Pratylenchus (such as


Pratylenchus neglectus, Pratylenchus penetrans


and


Pratylenchus curvitatus


), Tylenchulus (such as


Tylenchulus semipenetrans


), Tylenchorhynchus (such as Tylenchorhynchus dubius and


Tylenchorhynchus claytoni


), Rotylenchus (such as


Rotylencus robustus


), Heliocotylenchus (such as


Heliocotylenchus multicinctus


), Belonoaimus (such as


Belonoaimus longicaudatus


), Longidorus (such as


Longidorus elongatus


), Trichodorus (such as


Trichodorus primitivus


) and Xiphinema (such as


Xiphinema index


).




The nematode genera Ditylenchus (stem parasites, such as


Ditylenchus dipsaci


and


Ditylenchus destructor


), Aphelenchoides (leaf nematodes, such as


Aphelenchoides ritzemabosi


) and Anguina (blossom nematodes, such as


Anguina tritici


) can furthermore be controlled with the compounds according to the invention.




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




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




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




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




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




Combinations with other substances having a pesticidal action, fertilizers and/or growth regulators can be prepared on the basis of these formulations, for example in the form of a ready-to-use formulation or as a tank mix. Wettable powders are preparations which are uniformly dispersible in water and which, alongside the active compound, and in addition to a diluent or inert substance, also comprise wetting agents, for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols or alkyl- or alkylphenol-sulfonates, and dispersing agents, for example sodium ligninsulfonate or sodium 2,2′-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.




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




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




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




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




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




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




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




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




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




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




4. from the group of amidines amitraz, chlordimeform;




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




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




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




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




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




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




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




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




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











The examples below serve to illustrate the invention.




A. FORMULATION EXAMPLES




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




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




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




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




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




B. CHEMICAL EXAMPLES




Example No. 1




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




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






1


H-NMR (CDCl


3


, 300 MHz): d=1.41 (d, J=6.9 Hz, 6H), 3.22 (m, 1H), 7.78 (d, J=5 Hz,


1


H), 9.02 (d, J=5 Hz, 1H), 9.34 (s, 1H) ppm.




Example No. 2




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




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






1


H-NMR (CDCl


3


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




Example No. 3




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




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






1


H-NMR (CDCl


3


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




Example No. 4




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




500 mg of 4-trifluoromethylpyridine-3-thiocarboxamide and 440 mg of ethyl 4-chloroacetate were dissolved in 5 ml of dimethylformamide and heated at 100° C. for 4 hours. After cooling, the reaction mixture was poured onto ice-water and extracted with diethyl ether. The diethyl ether phase was dried (MgSO


4


), filtered and concentrated and the residue was purified by chromatography. This gave the desired product in pure form as a colorless oil.






1


H-NMR (CDCl


3


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




Example No. 5




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




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






1


H-NMR (CDCl


3


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




Example No. 6




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




1 g of 4-trifluoromethylnicotinic acid was admixed with 8 ml of thionyl chloride and heated at reflux temperature for 1 hour. After cooling, excess thionyl chloride was distilled off and the acyl chloride which remained as a pale yellow oil was taken up in 10 ml of dichloromethane. This solution was subsequently added dropwise to a solution of 930 mg of 2-amino-1-butanol and 1.06 g of triethylamine in 10 ml of dichloromethane cooled in an ice bath. After the addition had ended, stirring was continued for approximately 2 hours at room temperature. The mixture was poured into an ammonium chloride solution and extracted with ethyl acetate. The crude N-(1-hydroxy-2-butyl)-4-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.






1


H-NMR (CDCl


3


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




Example No. 7




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




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


2


SO


4


), concentration and chromatographic purification gave 624 mg of the desired product as a slightly brown oil.






1


H-NMR (CDCl


3


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




Example No. 8




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




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






1


H-NMR (CDCl


3


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




Example 9




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




Step 1: Tert-butyl 3-amino-3-(4-trifluoromethyl-3-pyridinecarbonyloxyimino)propionate




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






1


H-NMR (CDCl


3


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




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




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






1


H-NMR (CDCl


3


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




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




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




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




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






1


H-NMR (CDCl


3


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




Example No. 10




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




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




17.3 g of 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 g of the product as a white solid of mp. 172-174° C.




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




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




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




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




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




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




In a similar manner, it is possible to prepare the compounds shown in Tables 1 to 6 below. The abbreviations used denote




Ph: phenyl




THP: 2-tetrahydropyranyl












TABLE 1











































No.




X




Y




m




W




R


1






m.p.[° C.]




















1




N




CCl


3






0




O




CH


3









2




N




CCl


3






0




O




CH


2


CH


3








3




N




CCl


3






0




O




COOCH


2


CH


3








4




CH




CCl


3






0




O




CH


3








5




CH




CCl


3






0




O




COOCH


2


CH


3








6




N




(CF


2


)


3


CHCF


2






0




O




CH


3








7




N




(CF


2


)


3


CHCF


2






0




O




COOCH


2


CH


3








8




CH




(CF


2


)


3


CHCF


2






0




O




CH


3








9




CH




(CF


2


)


3


CHCF


2






0




O




COOCH


2


CH


3








10




N




(CF


2


)


3


CHCF


2






0




S




CH


2


COOC(CH


3


)


3








11




N




(CF


2


)


3


CHCF


2






0




S




CH


2


CONHCH


3








12




CH




(CF


2


)


3


CHCF


2






0




S




(CH


2


)


2


CH


3








13




CH




(CF


2


)


3


CHCF


2






0




S




COOCH


2


CH


3








14




N




(CF


2


)


2


CHCF


2






0




O




CH


2


CH


3








15




N




(CF


2


)


2


CHCF


2






0




O




COOCH


2


CH


3








16




N




(CF


2


)


2


CHCF


2






0




O




OH






17




N




(CF


2


)


2


CHCF


2






0




O




OCH


3








18




CH




(CF


2


)


2


CHCF


2






0




O




CH


3








19




CH




(CF


2


)


2


CHCF


2






0




O




COOCH


2


CH


3








20




CH




(CF


2


)


2


CHCF


2






0




O




OH






21




CH




(CF


2


)


2


CHCF


2






0




O




NHCH


3








22




N




CF


2


CF


3






0




O




CH


3








23




N




CF


2


CF


3






0




O




CH


2


CH


3








24




N




CF


2


CF


3






0




O




(CH


2


)


2


H


3








25




N




CF


2


CF


3






0




O




CH(CH


3


)


2








26




N




CF


2


CF


3






0




O




Cyclo-C


8


H


11








27




N




CF


2


CF


3






0




O




CH


2


C═CH


2








28




N




CF


2


CF


3






0




O




CH


2


C≡CH






29




N




CF


2


CF


3






0




O




CH


2


CH


2


C═CH






30




N




CF


2


CF


3






0




O




CH


2


C≡CCH


2


CH


3








31




N




CF


2


CF


3






0




O




(CH


2


)


4


C≡CH






32




N




CF


2


CF


3






0




O




CHFCF


3








33




N




CF


2


CF


3






0




O




COOCH


2


CH


3








34




N




CF


2


CF


3






0




O




CH


2


COOC(CH


3


)


3








35




N




CF


2


CF


3






0




O




CH


2


CONHCH


3








36




N




CF


2


CF


3






0




O




NH


2








37




N




CF


2


CF


3






0




O




NHCH


2


CH


3








38




CH




CF


2


CF


3






0




0




CH


3








39




CH




CF


2


CF


3






0




O




CH


2


CH


3








40




CH




CF


2


CF


3






0




O




(CH


2


)


2


CH


3








41




CH




CF


2


CF


3






0




O




CH(CH


3


)


2








42




CH




CF


2


CF


3






0




O




Cyclo-C


6


H


11








43




CH




CF


2


CF


3






0




O




CH


2


C═CH


2








44




CH




CF


2


CF


3






0




O




CH


2


COOC(CH


3


)


3








45




CH




CF


2


CF


3






0




O




NH


2








46




CH




CF


2


CF


3






0




O




NHCOCH


3








47




CH




CF


2


CF


3






0




O




NHCOCH


2


CH


3








48




N




CF


2


CF


3






0




S




CH


3








49




N




CF


2


CF


3






0




S




CH


2


CH


3








50




N




CF


2


CF


3






0




S




(CH


2


)


2


H


3








51




N




CF


2


Cl




0




O




CH


3








52




N




CF


2


Cl




0




O




CH


2


CH


3








53




N




CF


2


Cl




0




O




(CH


2


)


2


CH


3








54




N




CF


2


Cl




0




O




CH(CH


3


)


2








55




N




CF


2


Cl




0




O




CH


2


COOC(CH


3


)


3








56




N




CF


2


Cl




0




O




CH


2


CONHCH


3








57




N




CF


2


Cl




0




O




OH






58




N




CF


2


Cl




0




O




OCH


3








59




N




CF


2


Cl




0




O




OCH


2


CH


3








60




N




CF


2


Cl




0




O




NHCH


3








61




CH




CF


2


Cl




0




O




CH


3








62




CH




CF


2


Cl




0




O




CH


2


CH


3








63




CH




CF


2


Cl




0




O




(CH


2


)


2


H


3








64




CH




CF


2


Cl




0




O




CH(CH


3


)


2








65




CH




CF


2


Cl




0




O




CH


2


COOC(CH


3


)


3








66




CH




CF


2


Cl




0




O




CH


2


CONHCH


3








67




CH




CF


2


Cl




0




O




OH






68




CH




CF


2


Cl




0




O




OCH


3








69




CH




CF


2


Cl




0




O




OCH


2


CH


3








70




CH




CF


2


Cl




0




O




NHCH


3








71




CH




CF


2


Cl




0




O




Cyclo-C


6


H


11








72




CH




CF


2


Cl




0




O




CH


2


C═CH


2








73




CH




CF


2


Cl




0




O




COOCH


2


CH


3








74




CH




CF


2


Cl




0




O




CH


2


COOC(CH


3


)


3








75




CH




CF


2


Cl




0




O




CH


2


CONHCH


3








76




CH




CF


2


Cl




0




O




OCH


3








77




CH




CF


2


Cl




0




O




NHCH


3








78




CH




CF


3






0




O




CH


3






oil






79




CH




CF


3






0




O




CH


2


CH


3






oil






80




CH




CF


3






0




O




(CH


2


)


2


CH


3






oil






81




CH




CF


3






0




O




CH(CH


3


)


2






oil






82




CH




CF


3






0




O




Cyclo-C


3


H


5






oil






83




CH




CF


3






0




O




(CH


2


)


3


CH


3






oil






84




CH




CF


3






0




O




CH(CH


3


)CH


2


CH


3






oil






85




CH




CF


3






0




O




CH


2


CH(CH


3


)


2






oil






86




CH




CF


3






0




O




C(CH


3


)


3






oil






87




CH




CF


3






0




O




Cyclo-C


4


H


7








88




CH




CF


3






0




O




(CH


2


)


4


CH


3






oil






89




CH




CF


3






0




O




CH(CH


3


)(CH


2


)


2


CH


3








90




CH




CF


3






0




O




(CH


2


)


2


H(CH


3


)


2








91




CH




CF


3






0




O




CH


2


C(CH


3


)


3








92




CH




CF


3






0




O




Cyclo-C


5


H


9






oil






93




CH




CF


3






0




O




(CH


2


)


5


CH


3








94




CH




CF


3






0




O




C(CH


2


CH


3


)


2


CH


3








95




CH




CF


3






0




O




Cyclo-C


6


H


11








96




CH




CF


3






0




O




(CH


2


)


6


CH


3








97




CH




CF


3






0




O




CH(CH


3


)(CH


2


)


4


CH


3








98




CH




CF


3






0




O




Cyclo-C


7


H


13








99




CH




CF


3






0




O




CH


2


-cyclo-C


6


H


11








100




CH




CF


3






0




O




2-Norbornyl






101




CH




CF


3






0




O




(CH


2


)


7


CH


3








102




CH




CF


3






0




O




CH(CH


2


CH


3


)(CH


2


)


5


CH


3








103




CH




CF


3






0




O




(CH


2


)


8


CH


3








104




CH




CF


3






0




O




(CH


2


)


3


-cyclo-C


6


H


11








105




CH




CF


3






0




O




(CH


2


)


9


CH


3








106




CH




CF


3






0




O




1-Adamantyl






107




CH




CF


3






0




O




(CH


2


)


10


CH


3








108




CH




CF


3






0




O




(CH


2


)


11


CH


3








109




CH




CF


3






0




O




CH(CH


3


)(CH


2


)


9


CH


3








110




CH




CF


3






0




O




(CH


2


)


12


CH


3








111




CH




CF


3






0




O




(CH


2


)


13


CH


3








112




CH




CF


3






0




O




(CH


2


)


14


CH


3








113




CH




CF


3






0




O




(CH


2


)


15


CH


3








114




CH




CF


3






0




O




(CH


2


)


17


CH


3








115




CH




CF


3






0




O




(CH


2


)


19


CH


3








116




CH




CF


3






0




O




CHO






117




CH




CF


3






0




O




CH═CH


2






oil






118




CH




CF


3






0




O




CH


2


C═C(CH


3


)


2








119




CH




CF


3






0




O




CH


2


CH


2


C═CH


2








120




CH




CF


3






0




O




CH


2


C═CH


2








121




CH




CF


3






0




O




C(CH


3


)═CH


2








122




CH




CF


3






0




O




(E)-CH


2


CH═CHCH


2


CH


3








123




CH




CF


3






0




O




(Z)-CH


2


CH═CHCH


2


CH


3








124




CH




CF


3






0




O




(CH


2


)


5


C═CH


2








125




CH




CF


3






0




O




C(═CHCH


3


)CH


3






62-64






126




CH




CF


3






0




O




Geranyl






127




CH




CF


3






0




O




3-Menthyl






128




CH




CF


3






0




O




C≡CH






129




CH




CF


3






0




O




CH


2


C≡CH






130




CH




CF


3






0




O




CH


2


CH


2


C≡CH






131




CH




CF


3






0




O




CH


2


CH


2


C≡CH






132




CH




CF


3






0




O




(CH


2


)


4


C≡CH






133




CH




CF


3






0




O




CHFCF


3






oil






134




CH




CF


3






0




O




COOCH


2


CH


3






oil






135




CH




CF


3






0




O




CH


2


CH


2


OH




oil






136




CH




CF


3






0




O




CH


2


CH


2


OCH


3






oil






137




CH




CF


3






0




O




CH


2


COOC(CH


3


)


3






oil






138




CH




CF


3






0




O




CH


2


SC


6


H


5






oil






139




CH




CF


3






0




O




CH


2


CONHCH


3






109-111






140




CH




CF


3






0




O




CH


2


CH(OH)CH


2


OH






141




CH




CF


3






0




O




CH


2


COCH


3








142




CH




CF


3






0




O




COCH


3








143




CH




CF


3






0




O




CH


2


OC


8


H


5








144




CH




CF


3






0




O




COC


6


H


5








145




CH




CF


3






0




O




CO(4-Cl)-C


6


H


4








146




CH




CF


3






0




O




CF


2


CH


3








147




CH




CF


3






0




O




CH


2


CN






148




CH




CF


3






0




O




CH


2


CH


2


CN






149




CH




CF


3






0




O




CH


2


CH(—O—)CH


2








150




CH




CF


3






0




O




CH


2


(4-OCH


3


)C


6


H


5








151




CH




CF


3






0




O




CH


2


-cyclo-(4-Oxo)-C


6


H


8








152




CH




CF


3






0




O




CH


2


CH(OH)CH


2


SC


6


H


5








153




CH




CF


3






0




O




CH


2


CH


2


Si(CH


3


)


3








154




CH




CF


3






0




O




CH═CF


2








155




CH




CF


3






0




O




CCl═CHCl






156




CH




CF


3






0




O




2-Pyridyl




 99-101






157




CH




CF


3






0




O




2-Furyl






158




CH




CF


3






0




O




2-Thienyl




106-108






159




CH




CF


3






0




O




CH


2


C≡CCH


2


CH


2


OTHP






160




CH




CF


3






0




O




CH


2


CH


2


Cl




oil






161




CH




CF


3






0




O




Si(CH


3


)


3








162




CH




CF


3






0




O




OC


6


H


5








163




CH




CF


3






0




O




OH






164




CH




CF


3






0




O




OCH


3








165




CH




CF


3






0




O




OCH


2


CH


3








166




CH




CF


3






0




O




OCHF


2








167




CH




CF


3






0




O




OCH


2


C


6


H


5








168




CH




CF


3






0




O




CH


2


SCH


3






48-49






169




CH




CF


3






0




O




SC


6


H


5








170




CH




CF


3






0




O




SeC


6


H


5








171




CH




CF


3






0




O




NH


2






116-118






172




CH




CF


3






0




O




NHCH


3








173




CH




CF


3






0




O




NHCH


2


CH


3








174




CH




CF


3






0




O




N(CH


2


CH


3


)


2








175




CH




CF


3






0




O




CONHCH


2


C═CH


2






105-107






176




CH




CF


3






0




O




Cl






177




CH




CF


3






0




O




Br






178




CH




CF


3






0




O




CONH


2






206-208






179




CH




CF


3






0




O




NHCOCH


3






129-131






180




CH




CF


3






0




O




NHCOCH


2


CH


3








181




CH




CF


3






0




O




OSO


2


CH


3








182




CH




CF


3






0




O




SOCH


2


(4-Br)-C


6


H


4








183




CH




CF


3






0




O




N(CH


3


)COOCH


2


C


6


H


5








184




CH




CF


3






0




O




NHNH


2








185




CH




CF


3






0




O




NHN(CH


3


)


2








186




N




CF


3






0




O




CH


3








187




N




CF


3






0




O




CH


2


CH


3






oil






188




N




CF


3






0




O




(CH


2


)


2


CH


3






oil






189




N




CF


3






0




O




CH(CH


3


)


2






oil






190




N




CF


3






0




O




(CH


2


)


3


CH


3






oil






191




N




CF


3






0




O




CH


2


CH(CH


3


)


2






oil






192




N




CF


3






0




O




C(CH


3


)


3








193




N




CF


3






0




O




(CH


2


)


4


CH


3






oil






194




N




CF


3






0




O




CH(CH


3


)(CH


2


)


2


CH


3








195




N




CF


3






0




O




CH


2


C(CH


3


)


3








196




N




CF


3






0




O




Cyclo-C


5


H


9








197




N




CF


3






0




O




(CH


2


)


5


CH


3








198




N




CF


3






0




O




Cyclo-C


6


H


11








199




N




CF


3






0




O




CH(CH


3


)(CH


2


)


4


CH


3








200




N




CF


3






0




O




CH


2


cyclo-C


6


H


11








201




N




CF


3






0




O




(CH


2


)


7


CH


3








202




N




CF


3






0




O




(CH


2


)


8


CH


3








203




N




CF


3






0




O




(CH


2


)


9


CH


3








204




N




CF


3






0




O




CH(CH


3


)(CH


2


)


9


CH


3








205




N




CF


3






0




O




(CH


2


)


15


CH


3








206




N




CF


3






0




O




(CH


2


)


17


CH


3








207




N




CF


3






0




O




(CH


2


)


19


CH


3








208




N




CF


3






0




O




CH


2


CH═C(CH


3


)


2








209




N




CF


3






0




O




CH


2


CH


2


CH═CH


2








210




N




CF


3






0




O




CH


2


CH═CH


2








211




N




CF


3






0




O




(Z)-CH


2


CH═CHCH


2


CH


3








212




N




CF


3






0




O




(CH


2


)


5


CH═CH


2








213




N




CF


3






0




O




CH


2


C≡CH






214




N




CF


3






0




O




CH


2


C≡CCH


2


CH


3








215




N




CF


3






0




O




CHFCF


3








216




N




CF


3






0




O




COOCH


2


CH


3








217




N




CF


3






0




O




CH


2


CH


2


OH






218




N




CF


3






0




O




CH


2


CH


2


OCH


3








219




N




CF


3






0




O




CH


2


COOC(CH


3


)


3








220




N




CF


3






0




O




CH


2


SC


6


H


5








221




N




CF


3






0




O




CH


2


CONHCH


3








222




N




CF


3






0




O




CH


2


CH(OH)CH


2


OH






223




N




CF


3






0




O




CHO






224




N




CF


3






0




O




COCH


3








225




N




CF


3






0




O




CH


2


OC


6


H


5








226




N




CF


3






0




O




COC


6


H


5








227




N




CF


3






0




O




CF


2


CH


3








228




N




CF


3






0




O




CH


2


CN






229




N




CF


3






0




O




CH


2


CH


2


CN






230




N




CF


3






0




O




CH═CF


2








231




N




CF


3






0




O




2-Furyl






232




N




CF


3






0




O




CH


2


C≡C—I






233




N




CF


3






0




O




OH






234




N




CF


3






0




O




OCH


3








235




N




CF


3






0




O




OCH


2


CH


3








236




N




CF


3






0




O




OCHF


2








237




N




CF


3






0




O




OCH


2


C


6


H


5








238




N




CF


3






0




O




SC


6


H


5








239




N




CF


3






0




O




NH


2








240




N




CF


3






0




O




NHCH


3








241




N




CF


3






0




O




NHCH


2


CH


3








242




N




CF


3






0




O




N(CH


2


CH


3


)


2








243




N




CF


3






0




O




N(CH


2


CN)


2








244




N




CF


3






0




O




N(CH


3


)


2








245




N




CF


3






0




O




NHCOCH


3








246




N




CF


3






0




O




NHCOCH


2


CH


3








247




N




CF


3






0




O




OSO


2


CH


3








248




N




CF


3






0




O




NHNH


2








249




CH




CF


3






0




S




CH


3








250




CH




CF


3






0




S




CH


2


CH


3








251




CH




CF


3






0




S




(CH


2


)


2


CH


3








252




CH




CF


3






0




S




CHO






253




CH




CF


3






0




S




CHFCF


3








254




CH




CF


3






0




S




CH


2


C≡CH






255




CH




CF


3






0




S




COOCH


2


CH


3








256




CH




CF


3






0




S




CH


2


COOC(CH


3


)


3








257




CH




CF


3






0




S




CH


2


CN






258




CH




CF


3






0




S




SeC


6


H


5








259




N




CF


3






0




S




CH


3








260




N




CF


3






0




S




CH


2


CH


3








261




N




CF


3






0




S




(CH


2


)


2


CH


3








262




N




CF


3






0




S




CHFCF


3








263




N




CF


3






0




S




CH


2


CH


2


OH






264




N




CF


3






0




S




CH


2


COOC(CH


3


)


3








265




CH




CH


2


CH


2


Cl




0




O




CH


3








266




CH




CH


2


CH


2


Cl




0




O




CH


2


CH


3








267




CH




CH


2


CH


2


Cl




0




O




(CH


2


)


2


CH


3








268




CH




CH


2


CH


2


Cl




0




O




CH(CH


3


)


2








269




CH




CH


2


CH


2


Cl




0




O




CH


2


SC


6


H


5








270




CH




CH


2


CH


2


Cl




0




O




CH


2


CONHCH


3








271




CH




CH


2


CH


2


Cl




0




O




NH


2








272




CH




CH


2


CH


2


Cl




0




O




NHCH


2


CH


3








273




N




CH


2


CH


2


Cl




0




O




CH


2


CH


3








274




N




CH


2


CH


2


Cl




0




O




NH


2








275




N




CH


2


Cl




0




O




CH


3








276




CH




CH


2


Cl




0




O




CH


3








277




CH




CHF


2






0




O




CH


3








278




CH




CHF


2






0




O




CH


2


CH


3








279




CH




CHF


2






0




O




(CH


2


)


2


CH


3








280




CH




CHF


2






0




O




CH


2


CH═CH


2








281




CH




CHF


2






0




O




C(CH


3


)═CH


2








282




CH




CHF


2






0




O




COOCH


2


CH


3








283




CH




CHF


2






0




O




CH


2


CONHCH


3








254




CH




CHF


2






0




O




CF


2


CH


3








285




CH




CHF


2






0




O




CHO






286




CH




CHF


2






0




O




NH


2








287




CH




CHF


2






0




O




Cl






288




CH




CHF


2






0




O




NHCOCH


3








289




CH




CHF


2






0




O




NHNH


2








290




N




CHF


2






0




O




CH


3








291




N




CHF


2






0




O




CH


2


CH


3








292




N




CHF


2






0




O




CH(CH


3


)(CH


2


)


4


CH


3








293




N




CHF


2






0




O




CH


2


CH═CH


2








294




N




CHF


2






0




O




COOCH


2


CH


3








295




N




CHF


2






0




O




NH


2








296




CH




CF


3






1




O




CH


3








297




CH




CF


3






1




O




COOCH


2


CH


3








298




CH




CF


3






1




O




CH


2


COOC(CH


3


)


3








299




CH




CF


3






1




O




CHFCF


3








300




N




CF


3






0




O




CH


2


NHSO


2


CH


3








301




N




CF


3






0




O




(CH


2


)


2


NHSO


2


CH


3








302




N




CF


3






0




O




CH


2


NHSO


2


CH


2


CH


3








303




N




CF


3






0




O




CH


2


NHSO


2


CH


2


C


6


H


5








304




CH




CF


3






0




O




(CH


2


)


4


NHSO


2


CF


3








305




CH




CF


3






0




O




(CH


2


)


2


S(CH


2


)


2


CH


3








306




CH




CF


3






0




O




(CH


2


)


4


S(CH


2


)


4


OCH


3








307




CH




CF


3






0




S




(CH


2


)


2


S(CH


2


)


2


CN






308




CH




CF


3






0




S




CH


2


NHSO


2


CH


2


CH


3








309




CH




CF


3






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S




CH


2


NHSO


2


CH


2


C


6


H


5








310




CH




CF


3






0




S




(CH


2


)


2


NHSO


2


CH


3








311




CH




CF


3






0




S




CH


2


NHSO


2


CH


3








312




CH




CF


3






0




S




CH(CH


3


)CH


2


NHC


6


H


5








313




CH




CF


3






0




S




(CH


2


)


2


8(2-F)-C


6


H


4








314




CH




CF


3






0




S




(CH


2


)


6


NHCH


2


)


6


OCH


3








315




CH




CF


3






0




S




(CH


2


)


2


NH-(2-F)-C


6


H


4








316




CH




CF


3






0




S




(CH


2


)


3


NHCH


2


CN






317




CH




CF


3






0




S




(CH


2


)


2


0(3-Cl)—C


6


H


4








318




CH




CF


3






0




S




(CH


2


)


6


NHCH


2


CF


3








319




CH




CF


3






0




S




(CH


2


)


2


0(3-CH


3


)—C


6


H


4








320




CH




CF


3






0




O




CH


2


NHC


6


H


5








321




CH




CF


3






0




O




(CH


2


)


4


S(2-Br)—C


6


H


4








322




CH




CF


3






0




O




(CH


2


)


6


NH(CH


2


)


2


OCH


3








323




CH




CF


3






0




O




(CH


2


)


2


NH(CH


2


)


4


OCH


3








324




CH




CF


3






0




O




(CH


2


)


3


NH-(4-CN)—C


8


H


4








325




CH




CF


3






0




O




(CH


2


)


2


O(3-CH


3


)—C


6


H


4








326




CH




CF


3






0




O




(CH


2


)


4


NHCH


2


CF


3








327




CH




CF


3






0




O




(CH


2


)


4


NHCH


2


CN






328




CH




CF


3






0




O




(CH


2


)


3


O(4-OCH


3


)—C


6


H


4








329




CH




CF


3






0




O




CH


2


SO


2


-tert-C


4


H


9






oil






330




CH




CF


3






0




O




CH


2


SO


2


-(4-F)—C


6


H


4






oil






331




CH




CF


3






0




O




CH


2


SO


2


-C


6


H


5






oil






332




CH




CF


3






0




O




CH


2


SOCH


3






63






333




CH




CF


3






0




O




CH


2


SO—C


6


H


5






oil






334




CH




CF


3






0




O




CH


2


CONH(CH


2


)


2


H


3






80-82






335




CH




CF


3






0




O




(4-OCF


3


)—C


6


H


4






57-59






336




CH




CF


3






0




O




CH


2


OCH


3






oil













337




CH




CF


3






0




O
















53-54













338




CH




CF


3






0




O
















oil













339




CH




CF


3






0




O




CH


2


CH


2


OCH


2


CH


3






oil






340




CH




CF


3






0




O




CH


2


CH


2


NC


6


H


5






80-83













341




CH




CF


3






0




O
















80-81













342




CH




CF


3






0




O
















110-111













343




CH




CF


3






0




O




CH


2


CH


2


O(CO)-(4-Cl)—C


6


H


4






80-82






344




CH




CF


3






0




O




CH


2


-(4-OCH


3


)—C


6


H


4






54-55






345




CH




CF


3






0




O




CH


2


-(3-Cl)—C


6


H


4






51-52






346




CH




CF


3






0




O




CH


2


-cyclo-C


3


H


5






oil






347




CH




CF


3






0




O




CH


2


-(4-C


6


H


5


)—C


6


H


4






oil













348




CH




CF


3






0




O
















143-144













349




CH




CF


3






0




O




CH


2


CH


2


O(CO)-(2,6-F2)-C


6


H


3






57-58






350




CH




CF


3






0




O




CH


2


CH


2


O(CO)-(4-NO


2


)—C


6


H


4






80-81






351




CH




CF


3






0




O




CH


2


-(2,6-Cl


2


)—C


6


H


3






91-92






352




CH




CF


3






0




O




CH


2


CH


2


OSO


2


CH


3






oil






353




CH




CF


3






0




O




CH


2


CH


2


O(CO)-tert-C


4


H


9






oil






354




CH




CF


3






0




O




CH


2


-(3-F)—C


6


H


4






50—51






355




CH




CF


3






0




O




CH


2


CONCH


2


C≡CH




129-131






356




CH




CF


3






0




O




CH


2


CH


2


O(CO)-cyclo-C


3


H


7






oil






357




CH




CF


3






0




O




CH


2


CH


2


O(CO)CH


3






oil






358




CH




CF


3






0




O




CH


2


-[2,4-(CH


3


)


2


]-C


6


H


3






85-86






359




CH




CF


3






0




O




CH


2


CONCH


2


CH═CH


2






210-212






360




CH




CF


3






0




O




CH


2


CON(CH


2


CH


3


)


2






oil






361




CH




CF


3






0




O




CH


2


CON(CH


2


)


3


CH


3






77-79






362




CH




CF


3






0




O




CH


2


CONCH


2


-(2-furyl)




139-141






363




CH




CF


3






0




O




CH


2


CONCH(CH


3


)


2






112-114






364




CH




CF


3






0




O




CH


2


CONCH(CH


3


)[(CH


2


)


4


CH


3


]




73-75






365




CH




CF


3






0




O




CH


2


CONCH


2


CH


2


C


6


H


5






120-122






366




CH




CF


3






0




O




CH


2


CONCH


2


CH


2


OCH


2


CH


3






78






367




CH




CF


3






0




O




CH


2


CONCH


2


CF


3






176-178






368




CH




CF


3






0




O




CH


2


CONCH(CH


3


)[(CH


2


)


5


CH


3


]




85-86













369




CH




CF


3






0




O
















oil













370




CH




CF


3






0




O
















oil













371




CH




CF


3






0




O




CH


2


CH


2


-(1-pyrryl)




oil






372




CH




CF


3






0




O




CH


2


CH


2


C


6


H


5






oil






373




CH




CF


3






0




O




CH


2


Cl




53-54






374




CH




CF


3






0




O




(CH


2


)


3


OH




38-39






375




CH




CF


3






0




O




CH


2


CONCH(CH


3


)[(CH


2


)


2


]CH


3






68-69






376




CH




CF


3






0




O




CH


2


CH(OCH


3


)


2






oil






377




CH




CF


3






0




O




CH


2


CONCH


2


C(CH


3


)


3






oil






378




CH




CF


3






0




O




CH


2


CONC(CH


3


)


2


(CH


2


CH


3


)




oil






379




CH




CF


3






0




O




CH


2


CONCH


2


CH


2


-cyclo-C


6


H


11






82-85






380




CH




CF


3






0




O




CH


2


CONCH(CH


3


)(1-naphthyl)




142-146






381




CH




CF


3






0




O




(CH


2


)


3


Cl




oil






382




CH




CF


3






0




O




CH


2


CON-tert-C


4


H


9






oil






383




CH




CF


3






0




O




CH


2


CON(iso-C


3


H


7


)


2






70-72






384




CH




CF


3






0




O




CH


2


CON(CH


2


)


7


CH


3






79-81






385




CH




CF


3






0




O




CH


2


CON-cyclo-C


6


H


11






119-121






386




CH




CF


3






0




O




CH


2


CONCH


2


CH


2


-(4-Cl)-C


6


H


4






120-121






387




CH




CF


3






0




O




CH


2


CONCH


2


-(2-thienyl)




137-139













388




CH




CF


3






0




O
















151-153













389




CH




CF


3






0




O




CH


2


CONHCH(CH


3


)(CH


2


CH


3


)




87-89






390




CH




CF


3






0




O




(CH


2


)


3


SCH


3






oil






391




CH




CF


3






0




O




(CH


2


)


3


SOCH


3






oil






392




CH




CF


3






0




O




CH


2


CONC(CH


3


)


2


(C≡CH)




111-113






393




CH




CF


3






0




O




CH


2


CONCH(CH


3


)CH


2


CH


2


CH




72-74













394




CH




CF


3






0




O
















oil













395




CH




CF


3






0




O




CH


2


CON-cyclo-C


5


H


9






110-112






396




CH




CF


3






0




O




CH


2


CON(CH


2


)


4


CH


3






75-77













397




CH




CF


3






0




O
















190-192













398




CH




CF


3






0




O




CH


2


CON(3-CF


3


)C


6


H


4






136-138






399




CH




CF


3






0




O




CH


2


CON-cyclo-C


8


H


17






115-117













400




CH




CF


3






0




O
















oil













401




CH




CF


3






0




O




CH


2


CON-Adamantyl




oil






402




CH




CF


3






0




O




CH


2


CON(CH


2


CH


2


CH


3


)


2






oil






403




CH




CF


3






0




O




CH


2


CONCH(CH


3


)](4-F)-C


6


H


4


]




111-113






404




CH




CF


3






0




O




CH


2


CONCH


2


CH(CH


3


)


2






91-93













405




CH




CF


3






0




O
















Oil













406




CH




CF


3






0




O




CH


2


CONCH


2


CH


2


OC


6


H


5






 99-101






407




CH




CF


3






0




O




CH


2


CH═NOCH


3






oil






408




CH




CF


3






0




O




CH


2


CONCH


2


CH


2


-[3,4-(OCH


3


)


2


]C


6


H


3






123-125






409




CH




CF


3






0




O




CH


2


CON-(2-Cl)C


6


H


4






138-140






410




CH




CF


3






0




O




CH


2


CON-(2-SCH


3


)C


6


H


4






136-138













411




CH




CF


3






0




O
















222-225













412




CH




CF


3






0




O
















207-209













413




CH




CF


3






0




O




CH


2


CON-(3-Br)C


6


H


4






129-131






414




CH




CF


3






0




O




CH


2


CON-N-(2,4,6-Cl


3


)C


6


H


2






153-155






415




CH




CF


3






0




O




CH


2


CON-(4-I)C


6


H


4






143-145






416




CH




CF


3






0




O




CH


2


CON-NCOCH


2


(3-Thienyl)




185-187






417




CH




CF


3






0




O




CH


2


CH


2


CHO




oil






418




CH




CF


3






0




O




CH


2


CON(CH


3


)[(CH


2


)


3


CH


3


]




oil






419




CH




CF


3






0




O




CH


2


CON-(3,5-Cl


2


-2,4-F


2


)C


6


H




166-167






420




CH




CF


3






0




O




CH


2


CON-C


6


H


5






215-217






421




CH




CF


3






0




O




CH


2


CON(CH


3


)(C


6


H


11


)




oil






422




CH




CF


3






0




O




CH


2


CON(CH


2


CH


3


)(CH


2


CH═CH


2


) oil






423




CH




CF


3






0




O




CH


2


CON(CH


2


CH


3


)[CH(CH


3


)


2


]




oil






424




CH




CF


3






0




O




CH


2


CONCH(CH


3


)[(CH


3


)


2


]




108-110






425




CH




CF


3






0




O




CH


2


CON(CH


2


CH


3


)[CH


2


C(═CH


2


)(CH


3


]




oil






426




CH




CF


3






0




O




CH


2


CONCH


2


(4-tert-C


4


H


9


)C


6


H


4






oil






427




CH




CF


3






0




O




CH


2


CONCH(CH


3


)(tert-C


4


H


9


)




oil






428




CH




CF


3






0




O




CH


2


CONCH(CH


3


)[CH


2


CH(CH


3


)(CH


2


CH


3


)]




oil






429




CH




CF


3






0




O




CH


2


CONCH


2


COOCH


2


CH


3






103-105






430




CH




CF


3






0




O




CH


2


CON[(CH


2


)


2


CH


3


](CH


2


-cyclo-C


3


H


7


)




oil






431




CH




CF


3






0




O




CH


2


CONCH(CH


3


)CH


2


CH


2


CH(CH


3


)


2






80-82






432




CH




CF


3






0




O




CH


2


CONCH(CH


2


CH


3


)[CH


2


CH(CH


3


)


2


]




oil






433




CH




CF


3






0




O




CH


2


C═O-(1-Piperidinyl)




oil













434




CH




CF


3






0




O
















180-182













435




CH




CF


3






0




O




CH


2


CONCH


2


C(═CH


2


)(CH


3


)




86-87






436




CH




CF


3






0




O




CH


2


CONCH[CH(CH


3


)


2


](COOCH


3


)




oil






437




CH




CF


3






0




O




CH


2


CONCH


2


-cyclo-C


3


H


7






oil






438




CH




CF


3






0




O




CH


2


CON(CH


2


)


5


OH




oil






439




CH




CF


3






0




O




CH


2


CON(CH


3


)(CH


2


CO


2


CH


3


)




oil






440




CH




CF


3






0




O




CH


2


CON(CH


3


)(CH


2


CN)




oil






441




CH




CF


3






0




O




CH


2


CONCH[CH


2


CH(CH


3


)


2


](CO


2


CH


3


)




oil






442




CH




CF


3






0




O




CH


2


CON-(1-Piperidinyl)




oil






443




CH




CF


3






0




O




CH


2


CONCH


2


CH


2


OCH


3






97-99






444




CH




CF


3






0




O




CH


2


CH


2


SC


6


H


5






oil






445




CH




CF


3






0




O




CH


2


CH


2


SCH


3






oil






446




CH




CF


3






0




O




CH


2


CH


2


SCH


2


C


6


H


5






oil













447




CH




CF


3






0




O
















oil













448




CH




CF


3






0




O




CH


2


CON-(2-OH)C


6


H


4






162-164






449




CH




CF


3






0




O




CH


2


CON-(3-OH)C


6


H


4






oil






450




CH




CF


3






0




O




CH


2


CON-(2-CH


3


)C


6


H


4






163-164






451




CH




CF


3






0




O




CH


2


CON-(3-NO


2


)C


6


H


4






176-178






452




CH




CF


3






0




O




CH


2


CON-(3-OCF


2


CHFCl)C


6


H


4






120-121






453




CH




CF


3






0




O




CH


2


CON-(3-CF


3


-4-F)C


6


H


3






168-170






454




CH




CF


3






0




O




CH


2


CON-(2,4-Cl


2


)C


6


H


3






120-122






455




CH




CF


3






0




O




CH


2


CON-(2-F-4.Cl)C


6


H


3






148-151






456




CH




CF


3






0




O




CH


2


CON-[2,4-(CH


3


)


2


]C


6


H


3






123-125






457




CH




CF


3






0




O




CH


2


CON-[2,3-(CH


3


)


2


]C


6


H


3






waxy













458




CH




CF


3






0




O
















waxy













459




CH




CF


3






0




O




CH


2


CON-(2-CH


3


-3-Cl)C


6


H


3






160-162






460




CH




CF


3






0




O




CH


2


CON(CH


2


CH


3


)(C


6


H


5


)




oil













461




CH




CF


3






0




O
















124-126













462




CH




CF


3






0




O




CH


2


CON(2-OCH


3


-5-Ph)C


6


H


3






167-169













463




CH




CF


3






0




O
















157-158













464




CH




CF


3






0




O




CH


2


CON-(3-NO


2


-4-Cl)C


6


H


3






oil






465




CH




CF


3






0




O




CH


2


CON-(2-Cl-4-CH


3


)C


6


H


3






106-108






466




CH




CF


3






0




O




CH


2


CON-(3-OCH


2


CH


3


)C


6


H


4






waxy













467




CH




CF


3






0




O
















169-171













468




CH




CF


3






0




O




CH


2


CON-(4-CH


3


)C


6


H


4






139-141






469




CH




CF


3






0




O




CH


2


CON-(1-Naphthyl)




155-157






470




CH




CF


3






0




O




CH


2


CON-(3-I)C


6


H


4






135-137






471




CH




CF


3






0




O




CH


2


CON-(2-OCH


2


CH


3


)C


6


H


4






138






472




CH




CF


3






0




O




CH


2


CON-(2-OCH


3


)C


6


H


4






130-132






473




CH




CF


3






0




O




CH


2


CON-[3,5-(OCH


3


)


2


]C


6


H


3






130-132






474




CH




CF


3






0




O




CH


2


CON-(4-Cl)C


6


H


4






139-141






475




CH




CF


3






0




O




CH


2


CON-(3-CH


3


)C


6


H


4






oil






476




CH




CF


3






0




O




CH


2


CON-(3-OCH


3


)C


6


H


4






oil






477




CH




CF


3






0




O




CH


2


CON-(4-CH


2


CH


3


)C


6


H


4






122-123






478




CH




CF


3






0




O




CH


2


CON-(4-CF


3


)C


6


H


4






151-152






479




CH




CF


3






0




O




CH


2


CON-(2-CH


3


-4-Cl)C


6


H


3






165-167






480




CH




CF


3






0




O




CH


2


CH


2


NCH


2


C


6


H


5






oil






481




CH




CF


3






0




O




CH


2


CH


2


NCH


2


-(3-Pyridyl)




oil






482




CH




CF


3






0




O




CH


2


CH═NOCH


2


CH


3






oil






483




CH




CF


3






0




O




CH


2


CH═NOC


6


H


5






oil






484




CH




CF


3






0




O




CH


2


CON-(4-NO


2


)C


6


H


4






181-183






485




CH




CF


3






0




O




CH


2


CON-(2-CH


3


-4-NO


2


)C


6


H


3






129-131






486




CH




CF


3






0




O




CH


2


CON-(2-Cl-3-CF


3


)C


6


H


3






136






487




CH




CF


3






0




O




CH


2


CON-(2-CN-4-Cl)C


6


H


3






157-159






488




CH




CF


3






0




O




CH


2


CON-(3,5-Cl


2


)C


6


H


3






167-169






489




CH




CF


3






0




O




CH


2


CON-(3,5-Cl


2


-4-OCF


2


CHF


2


)C


6


H


2






132-134






490




CH




CF


3






0




O




CH


2


CON-(2,4,5-Cl


3


)C


6


H


2






146






491




CH




CF


3






0




O




CH


2


CON-(3,5-Cl


2


-4-OCF


2


CHFCF


3


)C


6


H


2






124-126






492




CH




CF


3






0




O




CH


2


CON-(2-CF


3


-4-Cl)C


6


H


3






136













493




CH




CF


3






0




O
















oil













494




CH




CF


3






0




O
















91-93













495




CH




CF


3






0




O
















123-125













496




CH




CF


3






0




O
















81-83













497




CH




CF


3






0




O
















113-115













498




CH




CF


3






0




O




COOH




155-157






499




CH




CF


3






0




O




4-F-C


6


H


4






104-106






500




CH




CF


3






0




O




CON(C


2


H


5


)


2






oil






501




CH




CF


3






0




O




CONCH(CH


3


)


2






oil






502




CH




CF


3






0




O




CON(CH


3


)


2






52-54






503




CH




CF


3






0




O




CONHCH


2


CCH




105-107






504




CH




CF


3






0




O




CONH-cyclo-C


3


H


5






101-103






505




CH




CF


3






0




O




CONH


2






206-208













506




CH




CF


3






0




O
















72-74













507




CH




CF


3






0




O
















 98-100













508




CH




CF


3






0




O
















108-110













509




CH




CF


3






0




O
















140-142













510




CH




CF


3






0




O




CONHCH


3






127-129






511




CH




CF


3






0




O




CONHCH


2


CH═CH


2






oil






512




CH




CF


3






0




O




CON(CH


2


CN)


2






90-92






513




CH




CF


3






0




O




4-(t-C


4


H


9


)-C


6


H


4






64-66






514




CH




CF


3






0




O




4-CF


3


—C


6


H


4






89-91






515




CH




CF


3






0




O




4-CH


3


-3-F-C


6


H


3






104-106






516




CH




CF


3






0




O




2,4-di-Cl—C


6


H


3






70-72






517




CH




CF


3






0




O




4-(NHSO


2


CH


3


)—C


6


H


4






204-206






518




CH




CF


3






0




O




2,6-di-Cl-C


6


H


3






139-141






519




CH




CF


3






0




O




COOCH


2


C


6


H


5






83-85






520




CH




CF


3






0




O




CONHC


3


H


7






oil






521




CH




CF


3






0




O




3,5-di-Br-4-(OCH


3


)—C


6


H


2






132-134






522




CH




CF


3






0




O




CHCl


2






oil






523




CH




CF


3






0




0




CCl


3






oil






524




CH




CF


3






0




O




CH(OCH


3


)


2






oil






525




CH




CF


3






0




O




3-CF


3


—C


6


H


4






57-59






526




CH




CF


3






0




O




CON(CH


2


)


5






oil






527




CH




CF


3






0




O




CON(CH


3


)CH


2


C


6


H


5






oil






528




CH




CF


3






0




O




CONHCH


2


C


6


H


5






96-98













529




CH




CF


3






0




O
















oil













530




CH




CF


3






0




O




CONH-n-C


6


H


13






oil






531




CH




CF


3






0




O




CON(CH


2


CH


3


)CH


2


C


6


H


5






oil






532




CH




CF


3






0




O




CONH-c-C


6


H


11






115-117






533




CH




CF


3






0




O




CON(n-C


4


H


9


)


2






oil













534




CH




CF


3






0




O
















oil













535




CH




CF


3






0




O




CONH-i-C


4


H


9






oil













536




CH




CF


3






0




O
















oil













537




CH




CF


3






0




O




CON(CH


2


)


4






68-70






538




CH




CF


3






0




O




CON(CH


3


)-n-C


6


H


13






oil













539




CH




CF


3






0




O
















oil













540




CH




CF


3






0




O




CON(CH


3


)CH


2


CH


3






oil






541




CH




CF


3






0




O




CONHOCH


3






oil













542




CH




CF


3






0




O
















oil













543




CH




CF


3






0




O




CON(CH


3


)CH


2


CH


2


CH


3






oil






544




CH




CF


3






0




O




CONHCH


2


CH(OCH


3


)


2






oil






545




CH




CF


3






0




O




CONH-t-C


4


H


9






113-115






546




CH




CF


3






0




O




CONHCH


2


-4-Cl-C


6


H


4






oil






547




CH




CF


3






0




O




CONHCH(CH


3


)C


6


H


5






oil






548




CH




CF


3






0




O




CONHCH


2


CH


2


OCH


3






92-94













549




CH




CF


3






0




O
















190-192













550




CH




CF


3






0




O




CONHC(CH


3


)


2


CCH




90-92






551




CH




CF


3






0




O




CONHCH


2


-2-Furyl




93-95






552




CH




CF


3






0




O




CON(CH


2


)


3






91-93






553




CH




CF


3






0




O




CONHCH


2


-c-C


3


H


5






oil






554




CH




CF


3






0




O




CONHC(CH


3


)


2


CH


2


CH


3






oil






555




CH




CF


3






0




O




CONH(CH


2


)


3


C


6


H


5






oil






556




CH




CF


3






0




O




CONHCH


2


-3-Pyridyl




132-134






557




CH




CF


3






0




O




CON(CH


3


)-n-C


4


H


9






oil






558




CH




CF


3






0




O




CON(CH


2


CH


3


)-i-C


3


H


7






oil













559




CH




CF


3






0




O
















oil













560




CH




CF


3






0




O




CONHCH


2


CH


2


Cl




oil






561




CH




CF


3






0




O




CONHCH


2


CN




152-157






562




CH




CF


3






0




O




CON(CH


3


)OCH


3






oil






563




CH




CF


3






0




O




CON(CH


3


)CH


2


CH═CH


2






oil






564




CH




CF


3






0




O




CONHCH


2


COOCH


3






oil






565




CH




CF


3






0




O




CON(CH


3


)-i-C


3


H


7






oil






566




CH




CF


3






0




O




CON(CH


3


)CH


2


CH


2


CN




oil






567




CH




CF


3






0




O




CON(CH


3


)CH


2


CH(OCH


3


)


2






oil






568




CH




CF


3






0




O




CON(CH


3


)CH


2


CH(—CH


2


CH


2


O—)




oil






569




CH




CF


3






0




O




CONHCH


2


C(═CH


2


)CHH


3






oil






570




CH




CF


3






0




O




CON(CH


2


CH


3


)CH


2


CH═CH


2






oil






571




CH




CF


3






0




O




CONHC


6


H


5






83-85






572




CH




CF


3






0




O




CON(CH


3


)CH


2


CCH




oil






573




CH




CF


3






0




O




CON(CH


3


)CH


2


CN




oil






574




CH




CF


3






0




O




CON(CH


3


)CH


2


CH


2


N(CH


3


)


2






oil






575




CH




CF


3






0




O




CONHOCH


2


CH


3






114-116






576




CH




CF


3






0




O




CONHCH


2


CF


3






74-76






577




CH




CF


3






0




O




CON(CH


2


CH


2


Cl)


2






oil






578




CH




CF


3






0




O




CONH-c-C


4


H


7






oil






579




CH




CF


3






0




O




CON(CH


2


CH


2


CH


3


)CH


2


-c-C


3


H


5






oil






580




CH




CF


3






0




O




CON(CH


3


)-c-C


6


H


11






oil






581




CH




CF


3






0




O




CON(CH


2


CH


3


)CH


2


C(═CH


2


)CH


3






oil






582




CH




CF


3






0




O




CONHOCH


2


CH═CH


2






90-92






583




CH




CF


3






0




O




CONHOCH


2


C


6


H


5






126-128






584




CH




CF


3






0




O




CON(CH


3


)CH


2


COOCH


3






oil






585




CH




CF


3






0




O




COONHCH


3






230-232






586




CH




CF


3






0




O




CONHCH


2


CH


3






83-85






587




CH




CF


3






0




O




CONHCH(CH


3


)COOCH


3






104-106






588




CH




CF


3






0




O




CONHCH(i-C


3


H


7


)COOCH


3






oil






589




CH




CF


3






0




O




CON(CH


3


)CH


2


CON(CH


3


)


2






oil






590




CH




CF


3






0




O




CON(CH


3


)-t-C


4


H


9






oil






591




CH




CF


3






0




O




CONHO-t-C


4


H


9






103-105






592




CH




CF


3






0




O




CON(CH


3


)CH(i-C


3


H


7


)COOCH


3






oil






593




CH




CF


3






0




O




CH(OCH


2


CH


3


)


2






oil













594




CH




CF


3






0




O
















oil













595




CH




CF


3






0




O
















oil













596




CH




CF


3






0




O
















oil













597




CH




CF


3






0




O
















oil













598




CH




CF


3






0




O
















oil













599




CH




CF


3






0




O




CONHCH


2


CONHCH


3






101-103






600




CH




CF


3






0




O




CON(CH


2


)


7






oil






601




CH




CF


3






0




O




CON(CH


2


)


6






oil






602




CH




CF


3






0




O




CON(CH


2


CH


3


)CH


2


CH


2


OCH


3






oil













603




CH




CF


3






0




O
















oil













604




CH




CF


3






0




O
















oil













605




CH




CF


3






0




O
















oil













606




CH




CF


3






0




O




CON(CH


2


CH


3


)CH


2


CH


2


CN




oil













607




CH




CF


3






0




O
















oil













608




CH




CF


3






0




O




CON(CH


2


CH


3


)-n-C


4


H


9






oil













609




CH




CF


3






0




O
















179-181













610




CH




CF


3






0




O




CONHCH(CH


3


)CONHCH


3






136-138






611




CH




CF


3






0




O




COON(CH


2


)


4






64-66






612




CH




CF


3






0




O




CONHCH


2


CON(CH


3


)


2






107-109






613




CH




CF


3






0




O




CON(CH


2


COOCH


2


CH


3


)


2






oil













614




CH




CF


3






0




O
















180-182













615




CH




CF


3






0




O
















221-223













616




CH




CF


3






0




O
















234-236













617




CH




CF


3






0




O
















oil













618




CH




CF


3






0




O




CON(CH


3


)CH


2


-6-Cl-3-pyridyl




oil













619




CH




CF


3






0




O
















105-107













620




CH




CF


3






0




O




CONHCH(CH


3


)CH(OCH


3


)


2






oil






621




CH




CF


3






0




O




CONHCH


2


CH


2


SCH


3






oil






622




CH




CF


3






0




O




CONHCH(CH


3


)CH


2


OCH


3






70-72






623




CH




CF




0




O




CONHCH


2


CH


2


NHCOCH


3






124-126






624




CH




CF


3






0




O




CONH(CH


2


)


3


OCH


2


CH


3






oil






625




CH




CF


3






0




O




CON(CH


2


CH


3


)CH


2


CH


2


CH


3






oil






626




CH




CF


3






0




O




CON(CH


2


CH


3


)CH


2


OCH


3






oil






627




CH




CF


3






0




O




CONHCH


2


CH


2


SCH


2


CH


3






oil






628




CH




CF


3






0




O




CONHCH


2


CH


2


OCH


2


CH


3






59-61













629




CH




CF


3






0




O
















oil













630




CH




CF


3






0




O
















174-176













631




CH




CF


3






0




O




CONHCH(CH


3


)CH(OCH


3


)


2






oil






632




CH




CF


3






0




O




CONHCH


2


CH


2


SCH


3






oil






633




CH




CF


3






0




O




CONHCH(CH


3


)CH


2


OCH


3






70-72






634




CH




CF


3






0




O




CONHCH


2


CH


2


NHCOCH


3






124-126






635




CH




CF


3






0




O




CONH(CH


2


)


3


OCH


2


CH


3






oil






636




CH




CF


3






0




O




CON(CH


2


CH


3


)CH


2


CH


2


CH


3






oil






637




CH




CF


3






0




O




CON(CH


2


CH


3


)CH


2


OCH


3






oil






638




CH




CF


3






0




O




CONHCH


2


CH


2


SCH


2


CH


3






oil






639




CH




CF


3






0




O




CONHCH(CH


3


)CH


2


COOCH


2


CH


3






oil






640




CH




CF


3






0




O




CONH-4-COOCH


3


—C


6


H


4






189-191






641




CH




CF


3






0




O




CONH-4-CONH


2


—C


6


H


4






265-267






642




CH




CF


3






0




O




CONHCH


2


CH


2


Br




oil






643




CH




CF


3






0




O




CONHCH


2


CH═CHCH


2


Cl




oil






644




CH




CF


3






0




O




CONH-4-CONHCH


3


—C


6


H


4






219-221






645




CH




CF


3






0




O




CONHCH


2


CH


2


CH


2


Br




oil






646




CH




CF


3






0




O




CONHCH


2


CH


2


CH


2


OCH


3






oil






647




CH




CF


3






0




O




CONH-4-CH


2


CH


3


—C


6


H


4






97-99






648




CH




CF


3






0




O




CONHCH


2


CH


2


OCH(CH


3


)


2






oil






649




CH




CF


3






0




O




CONHCH


2


CH


2


CH


2


OCH


2


CH


3






oil













650




CH




CF


3






0




O
















oil













651




CH




CF


3






0




O
















64-66













652




CH




CF


3






0




O
















oil













653




CH




CF


3






0




O
















oil













654




CH




CF


3






0




O




CH


2


CON(CH


3


)CH


2


CH


3






oil






655




CH




CF


3






0




O




CH


2


CON(CH


3


)


2






58-60






656




CH




CF


3






0




O




CH


2


CON(CH


2


)


4






101-103













657




CH




CF


3






0




O
















oil













658




CH




CF


3






0




O
















90-92













659




CH




CF


3






0




O




CH


2


CONHCH


2


CH


3






104-106






660




CH




CF


3






0




O




CH


2


CON(CH


3


)CH


2


CH


2


OH




oil






661




CH




CF


3






0




O




CH


2


CON(CH


3


)CH


2


CH


2


CH


3






oil






662




CH




CF


3






0




O




CH


2


CON(CH


3


)CH


2


CH




oil











(—OCH


2


CH


2


O—)






663




CH




CF


3






0




O




CH


2


CONHCH


2


CH


3






104-106






664




CH




CF


3






0




O




CH


2


CON(CH


3


)CH


2


CH


2


OH




oil






665




CH




CF


3






0




O




CH


2


CON(CH


3


)CH


2


CH


2


CH


3






oil






667




CH




CF


3






0




O




CH


2


CON(CH


3


)CH


2


CH




oil











(—OCH


2


CH


2


O—)













668




CH




CF


3






0




O
















79-81













669




CH




CF


3






0




O




CH


2


CONHCH


2


CH


2


SCH


3






65-67






670




CH




CF


3






0




O




CH


2


CONHCH(CH


3


)CH


2


OCH


3






86-88






671




CH




CF


3






0




O




CON(CH


3


)CH


2


CH


2


OCO-c-C


4


H


7






oil






672




CH




CF


3






0




O




CH


2


CONHCH


2


CH


2


Br




87-89






673




CH




CF


3






0




O




CON(CH


3


)CH


2


CH


2


OCOC


6


H


5






oil






674




CH




CF


3






0




O




CON(CH


3


)CH


2


CH


2


OCO-c-C


3


H


5






oil






675




CH




CF


3






0




O




CONH-2-CH


3


—C


6


H


4






104-106






676




CH




CF


3






0




O




CH


2


CON(i-C


3


H


7


)-4-F—C


6


H


4






102-104













677




CH




CF


3






0




O
















oil













678




CH




CF


3






0




O
















oil













679




CH




CF


3






0




O




CON(CH


3


)CH


2


CH


2


OCONHC


6


H


5






100-102






680




CH




CF


3






0




O




CON(CH


3


)CH


2


CH


2


OCONHCH


2


CH


3






oil






681




CH




CF


3






0




O




CON(CH


3


)CH


2


CH


2


OSO


2


CH


3






oil






682




CH




CF


3






0




O




CH


2


CONH-c-C


4


H


7






133-135






683




CH




CF


3






0




O




CH


2


CONHCH


2


CN




158-160






















TABLE 2










































No.




X




Y




W




R


1






m.p.[° C.]









684




N




(CF


2


)


3


CHF


2






O




CH


3









685




N




(CF


2


)


2


CF


3






O




CH


2


CH


3








686




N




(CF


2


)


2


CF


3






O




COOCH


2


CH


3








687




N




(CF


2


)


2


CF


3






O




OH






688




N




(CF


2


)


2


CF


3






O




OCH


3








689




N




CF


2


CF


3






O




CH


3








690




N




CF


2


CF


3






O




CH


2


CH


3








691




N




CF


2


CF


3






S




CH


3








692




N




CF


2


CF


3






S




CH


2


CH


3








693




N




CF


2


CF


3






S




(CH


2


)


2


CH


3








694




CH




CF


3






O




CH


3






oil






695




CH




CF


3






O




CH


2


CH


3








696




CH




CF


3






O




(CH


2


)


2


CH


3








697




CH




CF


3






O




CH(CH


3


)


2








698




CH




CF


3






O




(CH


2


)


3


CH


3








699




CH




CF


3






O




CH(CH


3


)CH


2


CH


3








700




CH




CF


3






O




CH


2


CH(CH


3


)


2








701




CH




CF


3






O




C(CH


3


)


3






oil






702




CH




CF


3






O




(CH


2


)


4


CH


3








703




CH




CF


3






O




CH(CH


3


)(CH


2


)


2


CH


3








704




CH




CF


3






O




(CH


2


)


2


CH(CH


3


)


2








705




CH




CF


3






O




CH


2


C(CH


3


)


3








706




CH




CF


3






O




Cyclo-C


5


H


9








707




CH




CF


3






O




Cyclo-C


6


H


11








708




CH




CF


3






O




CHO






709




CH




CF


3






O




CH═CH


2








710




CH




CF


3






O




CH


2


CH═C(CH


3


)


2








711




CH




CF


3






O




CH


2


CH═CH


2








712




CH




CF


3






O




C(CH


3


)═CH


2








713




CH




CF


3






O




(CH


2


)


5


C═CH


2








714




CH




CF


3






O




C(═CHCH


3


)CH


3








715




CH




CF


3






O




CH


2


C≡CH






716




CH




CF


3






O




CH


2


CH


2


C≡CH






717




CH




CF


3






O




CH


2


C≡CCH


2


CH


3








718




CH




CF


3






O




(CH


2


)


4


C≡CH






719




CH




CF


3






O




CHFCF


3








720




CH




CF


3






O




COOCH


2


CH


3








721




CH




CF


3






O




CH


2


CH


2


OH






722




CH




CF


3






O




CH


2


CH


2


OCH


3








723




CH




CF


3






O




CH


2


COOC(CH


3


)


3








724




CH




CF


3






O




CH


2


SC


6


H


5








725




CH




CF


3






O




CH


2


CONHCH


3








726




CH




CF


3






O




CH


2


CH(OH)CH


2


OH






727




CH




CF


3






O




CH


2


COCH


3








728




CH




CF


3






O




COCH


3








729




CH




CF


3






O




CH


2


OC


6


H


5








730




CH




CF


3






O




COC


6


H


5








731




CH




CF


3






O




CF


2


CH


3








732




CH




CF


3






O




CH


2


CN






733




CH




CF


3






O




CH


2


CH(—O—)CH


2








734




CH




CF


3






O




CH


2


(4-OCH


3


)C


6


H


5








735




CH




CF


3






O




CH


2


CH(OH)CH


2


SC


6


H


5








736




CH




CF


3






O




CH═CF


2








737




CH




CF


3






O




CCl═CHCl






738




CH




CF


3






O




2-Pyridyl






739




CH




CF


3






O




OC


6


H


5








740




CH




CF


3






O




OH






741




CH




CF


3






O




OCH


3








742




CH




CF


3






O




OCH


2


CH


3








743




CH




CF


3






O




OCHF


2








744




CH




CF


3






O




OCH


2


C


6


H


5








745




CH




CF


3






O




SCH


3








746




CH




CF


3






O




SC


6


H


5








747




CH




CF


3






O




NH


2








748




CH




CF


3






O




NHCH


3








749




CH




CF


3






O




NHCH


2


CH


3








750




CH




CF


3






O




N(CH


2


CH


3


)


2








751




CH




CF


3






O




N(CH


2


CN)


2








752




CH




CF


3






O




N(CH


3


)


2








753




CH




CF


3






O




NHCOCH


3








754




CH




CF


3






O




NHCOCH


2


CH


3








755




CH




CF


3






O




OSO


2


CH


3








756




CH




CF


3






O




SOCH


2


(4-Br)-C


6


H


4








757




CH




CF


3






O




N(CH


3


)COOCH


2


C


6


H


5








758




N




CF


3






O




CH


3








759




N




CF


3






O




CH


2


CH


3








760




N




CF


3






O




(CH


2


)


2


CH


3








761




N




CF


3






O




CH(CH


3


)


2








762




N




CF


3






O




(CH


2


)


3


CH


3








763




N




CF


3






O




CH


2


CH(CH


3


)


2








764




N




CF


3






O




C(CH


3


)


3








765




N




CF


3






O




CH


2


C(CH


3


)


3








766




N




CF


3






O




Cyclo-C


5


H


9








767




N




CF


3






O




Cyclo-C


6


H


11








768




N




CF


3






O




CH


2


C═C(CH


3


)


2








769




N




CF


3






O




CH


2


CH


2


C═CH


2








770




N




CF


3






O




CH


2


CH═CH


2








771




N




CF


3






O




(CH


2


)


5


CH═CH


2








772




N




CF


3






O




CH


2


C≡CH






773




N




CF


3






O




CH


2


C≡CCH


2


CH


3








774




N




CF


3






O




CHFCF


3








775




N




CF


3






O




COOCH


2


CH


3








776




N




CF


3






O




CH


2


CH


2


OH






777




N




CF


3






O




CH


2


CH


2


OCH


3








778




N




CF


3






O




CH


2


COOC(CH


3


)


3








779




N




CF


3






O




CH


2


SC


6


H


5








780




N




CF


3






O




CH


2


CONHCH


3








781




N




CF


3






O




CH


2


CH(OH)CH


2


OH






782




N




CF


3






O




CHO






783




N




CF


3






O




COCH


3








784




N




CF


3






O




CH


2


OC


6


H


5








785




N




CF


3






O




COC


6


H


5








786




N




CF


3






O




CF


2


CH


3








787




N




CF


3






O




CH


2


CN






788




N




CF


3






O




CH


2


CH


2


CN






789




N




CF


3






O




CH═CF


2








790




N




CF


3






O




2-Furyl






791




N




CF


3






O




OH






792




N




CF


3






O




OCH


3








793




N




CF


3






O




OCH


2


CH


3








794




N




CF


3






O




OCHF


2








795




N




CF


3






O




OCH


2


C


6


H


5








796




N




CF


3






O




NH


2








797




N




CF


3






O




NHCH


3








798




N




CF


3






O




NHCH


2


CH


3








799




N




CF


3






O




N(CH


2


CH


3


)


2








800




N




CF


3






O




N(CH


2


CN)


2








801




N




CF


3






O




N(CH


3


)


2








802




N




CF


3






O




NHCOCH


3








803




N




CF


3






O




NHCOCH


2


CH


3








804




N




CF


3






O




OSO


2


CH


3








805




CH




CF


3






S




CH


3








806




CH




CF


3






S




CH


2


CH


3








807




CH




CF


3






S




(CH


2


)


2


CH


3








808




CH




CF


3






S




CHO






809




CH




CF


3






S




CHFCF


3








810




CH




CF


3






S




CH


2


C≡CH






811




CH




CF


3






S




COOCH


2


CH


3








812




CH




CF


3






S




CH


2


COOC(CH


3


)


3








813




CH




CF


3






S




CH


2


CN






814




N




CF


3






S




CH


3








815




N




CF


3






S




CH


2


CH


3








816




N




CF


3






S




(CH


2


)


2


CH


3








817




N




CF


3






S




CHFCF


3








818




N




CF


3






S




CH


2


CH


2


OH






819




N




CF


3






S




CH


2


COOC(CH


3


)


3








820




N




CH


2


CH


2


Cl




O




CH


2


CH


3








821




N




CH


2


CH


2


Cl




O




NH


2








822




N




CH


2


Cl




O




CH


3








823




CH




CHF


2






O




CH


3








824




CH




CHF


2






O




CH


2


CH


3








825




CH




CHF


2






O




(CH


2


)


2


CH


3








826




CH




CHF


2






O




CH


2


C═CH


2








827




CH




CHF


2






O




C(CH


3


)═CH


2








828




CH




CHF


2






O




COOCH


2


CH


3








829




CH




CHF


2






O




CH


2


CONHCH


3








830




CH




CHF


2






O




CF


2


CH


3








831




CH




CHF


2






O




CHO






832




CH




CHF


2






O




NH


2








833




CH




CHF


2






O




NHCOCH


3








834




N




CHF


2






O




CH


3








835




N




CHF


2






O




CH


2


CH


3








836




N




CHF


2






O




CH(CH


3


)(CH


2


)


4


CH


3








837




N




CHF


2






O




CH


2


CH═CH


2








838




N




CHF


2






O




COOCH


2


CH


3








839




N




CHF


2






O




NH


2
























TABLE 3











































No.




X




Y




m




V




R


1






m.p.[° C.]




















840




N




(CF


2


)


3


CHF


2






0




O




CH


3









841




N




(CF


2


)


2


CF


3






0




O




CH


2


CH


3








842




N




(CF


2)




2


CF


3






0




O




COOCH


2


CH


3








843




N




(CF


2)




2


CF


3






0




O




SH






844




N




(CF


2)




2


CF


3






0




O




SCH


3








845




N




(CF


2)




2


CF


3






0




O




SCH


2


C≡CH






846




N




CF


2CF




3






0




O




CH


3








847




N




CF


2CF




3






0




O




CH


2


CH


3








848




N




CF


3






0




O




CH


3








849




N




CF


3






0




O




CH


2


CH


3








850




N




CF


3






0




O




(CH


2


)


2


CH


3








851




N




CF


3






0




O




CH(CH


3


)


2








852




N




CF


3






0




O




(CH


2


)


3


CH


3








853




N




CF


3






0




O




CH


2


CH(CH


3


)


2








854




N




CF


3






0




O




C(CH


3


)


3








855




N




CF


3






0




O




CH


2


C(CH


3


)


3








856




N




CF


3






0




O




Cyclo-C


5


H


9








857




N




CF


3






0




O




Cyclo-C


6


H


11








858




N




CF


3






0




O




CH


2


CH═C(CH


3


)


2








859




N




CF


3






0




O




CH


2


CH


2


CH═CH


2








860




N




CF


3






0




O




CH


2


CH═CH


2








861




N




CF


3






0




O




(CH


2


)


5


CH═CH


2








862




N




CF


3






0




O




CH


2


C≡CH






863




N




CF


3






0




O




CH


2


C≡CCH


2


CH


3








864




N




CF


3






0




O




CHFCF


3








865




N




CF


3






0




O




COOCH


2


CH


3








866




N




CF


3






0




O




CH


2


CH


2


OH






867




N




CF


3






0




O




CH


2


CH


2


OCH


3








868




N




CF


3






0




O




CH


2


COOC(CH


3


)


3








869




N




CF


3






0




O




CH


2


SPh






870




N




CF


3






0




O




CH


2


CONHCH


3








871




N




CF


3






0




O




CH


2


CH(OH)CH


2


O






872




N




CF


3






0




O




CHO






873




N




CF


3






0




O




COCH


3








874




N




CF


3






0




O




CH


2


OC


6


H


5








875




N




CF


3






0




O




COPh






876




N




CF


3






0




O




CF


2


CH


3








877




N




CF


3






0




O




CH


2


CN






878




N




CF


3






0




O




CH


2


CH


2


CN






879




N




CF


3






0




O




CH═CF


2








880




N




CF


3






0




O




2-Furyl






881




N




CF


3






0




O




OH






882




N




CF


3






0




O




OCH


3








883




N




CF


3






0




O




OCH


2


CH


3








884




N




CF


3






0




O




OCHF


2








885




N




CF


3






0




O




OCH


2


Ph






886




N




CF


3






0




O




NH


2








887




N




CF


3






0




O




NHCH


3








888




N




CF


3






0




O




NHCH


2


CH


3








889




N




CF


3






0




O




N(CH


2


CH


3


)


2








890




N




CF


3






0




O




N(CH


2


CN)


2








891




N




CF


3






0




O




N(CH


3


)


2








892




N




CF


3






0




O




NHCOCH


3








893




N




CF


3






0




O




NHCOCH


2


CH


3








894




N




CF


3






0




O




OSO


2


CH


3








895




N




CH


2


CH


2


Cl




0




O




CH


2


CH


3








896




N




CH


2


CH


2


Cl




0




O




NH


2








897




N




CH


2


Cl




0




O




CH


3








898




N




CHF


2






0




O




CH


3








899




N




CHF


2






0




O




CH


2


CH


3








900




N




CHF


2






0




O




CH(CH


3


)(CH


2


)


4


CH


3








901




N




CHF


2






0




O




CH


2


CH═CH


2








902




N




CHF


2






0




O




COOCH


2


CH


3








903




N




CHF


2






0




O




NH


2








904




CH




CF


3






0




O




CH


3






60-61






905




CH




CF


3






1




O




CH


3








906




CH




CF


3






0




O




CH


2


CH


3






oil






907




CH




CF


3






1




O




CH


2


CH


3






oil






908




CH




CF


3






0




O




(CH


2


)


2


CH


3






oil






909




CH




CF


3






1




O




(CH


2


)


2


CH


3






oil






910




CH




CF


3






0




O




CH(CH


3


)


2








911




CH




CF


3






1




O




CH(CH


3


)


2








912




CH




CF


3






0




O




(CH


2


)


3


CH


3








913




CH




CF


3






1




O




(CH


2


)


3


CH


3








914




CH




CF


3






0




O




CH(CH


3


)CH


2


CH


3








915




CH




CF


3






1




O




CH(CH


3


)CH


2


CH


3








916




CH




CF


3






0




O




CH


2


CH(CH


3


)


2








917




CH




CF


3






1




O




CH


2


CH(CH


3


)


2








918




CH




CF


3






0




O




C(CH


3


)


3








919




CH




CF


3






1




O




C(CH


3


)


3








920




CH




CF


3






0




O




(CH


2


)


4


CH


3








921




CH




CF


3






1




O




(CH


2


)


4


CH


3








922




CH




CF


3






0




O




CH(CH


3


)(CH


2


)


2


CH


3








923




CH




CF


3






0




O




(CH


2


)


2


CH(CH


3


)


2








924




CH




CF


3






0




O




CH


2


C(CH


3


)


3








925




CH




CF


3






0




O




cyclo-C


5


H


9








926




CH




CF


3






0




O




cyclo-C


6


H


11








927




CH




CF


3






0




O




CH


2


(3-Thienyl)




oil






928




CH




CF


3






0




O




CHO






929




CH




CF


3






0




O




CH═CH


2








930




CH




CF


3






0




O




CH


2


Ph




61-63






931




CH




CF


3






0




O




CH


2


CH═C(CH


3


)


2








932




CH




CF


3






0




O




CH


2


CH═CH


2








933




CH




CF


3






0




O




C(CH


3


)═CH


2








934




CH




CF


3






0




O




(CH


2


)


5


C═CH


2








935




CH




CF


3






0




O




C(═CHCH


3


)CH


3








936




CH




CF


3






0




O




CH


2


C≡CH






937




CH




CF


3






0




O




CH


2


CH


2


C≡CH


2








938




CH




CF


3






0




O




CH


2


C≡CCH


2


CH


3








939




CH




CF


3






0




O




(CH


2


)


4


C≡CH






940




CH




CF


3






0




O




CHFCF


3








941




CH




CF


3






0




O




COOCH


2


CH


3








942




CH




CF


3






0




O




CH


2


CH


2


OH






943




CH




CF


3






0




O




CH


2


CH


2


OCH


3








944




CH




CF


3






0




O




CH


2


COOC(CH


3


)


3








945




CH




CF


3






0




O




CH


2


SPh






946




CH




CF


3






0




O




CH


2


CONHCH


3








947




CH




CF


3






0




O




CH


2


CH(OH)CH


2


OH






948




CH




CF


3






0




O




CH


2


COCH


3








949




CH




CF


3






0




O




COCH


3








950




CH




CF


3






0




O




CH


2


Oph






951




CH




CF


3






0




O




COPh






952




CH




CF


3






0




O




CF


2


CH


3








953




CH




CF


3






0




O




CH


2


CN




oil






954




CH




CF


3






0




O




CH


2


CH(—O—)CH


2








955




CH




CF


3






0




O




CH


2


(4-OCH


3


)Ph






956




CH




CF


3






0




O




CH


2


CH(OH)CH


2


SPh






957




CH




CF


3






0




O




CH═CF


2








958




CH




CF


3






0




O




CCl═CHCl






959




CH




CF


3






0




O




Ph




120-121






960




CH




CF


3






0




O




2-Thienyl




87-89






961




CH




CF


3






0




O




OPh






962




CH




CF


3






0




O




OH






963




CH




CF


3






0




O




OCH


3








964




CH




CF


3






0




O




OCH


2


CH


3








965




CH




CF


3






0




O




OCHF


2








966




CH




CF


3






0




O




OCH


2


Ph






967




CH




CF


3






0




O




SCH


3








968




CH




CF


3






0




O




SPh






969




CH




CF


3






0




O




NH


2






190-191






970




CH




CF


3






0




O




NHCH


3








971




CH




CF


3






0




O




NHCH


2


CH


3








972




CH




CF


3






0




O




N(CH


2


CH


3


)


2








973




CH




CF


3






0




O




N(CH


2


CN)


2








974




CH




CF


3






0




O




N(CH


3


)


2








975




CH




CF


3






0




O




NHCOCH


3








976




CH




CF


3






0




O




NHCOCH


2


CH


3








977




CH




CF


3






0




O




OSO


2


CH


3








978




CH




CF


3






0




O




SOCH


2


(4-Br)-C


6


H


4








979




CH




CF


3






0




O




N(CH


3


)COOCH


2


Ph






980




CH




CF


3






0




NCH


3






CH


3








981




CH




CF


3






0




NCH


2


CH


3






CH


3








982




CH




CF


3






0




NCH


2


CH


3






CH


2


CH


3








983




CH




CF


3






0




NCH


2


CN




CH


2


CH


3








984




CH




CF


3






0




NCH


2


OCH


3






NHCH


3








985




CH




CF


3






0




NCH


2


OCH


2


CH


3






CN






986




CH




CF


3






0




NCH


2


CH═CH


2






CH


3








9B7




CH




CF


3






0




NCH


2


CH═CF


2






SCH


3








988




CH




CF


3






0




NCH


2


OCH


3






SCH


2


CH


3








989




CH




CF


3






0




NCH


2


OCH


3






SCH


2


Ph






990




CH




CHF


2






0




O




CH


3








991




CH




CHF


2






0




O




CH


2


CH


3








992




CH




CHF


2






0




O




(CH


2


)


2


CH


3








993




CH




CHF


2






0




O




CH


2


CH═CH


2








994




CH




CHF


2






0




O




C(CH


3


)═CH


2








995




CH




CHF


2






0




O




COOCH


2


CH


3








996




CH




CHF


2






0




O




CH


2


CONHCH


3








997




CH




CHF


2






0




O




CF


2


CH


3








998




CH




CHF


2






0




O




CHO






999




CH




CHF


2






0




O




NH


2








1000




CH




CHF


2






0




O




NHCOCH


3








1001




N




CF2CF


3






0




S




CH


3








1002




N




CF2CF


3






0




S




CH


2


CH


3








1003




N




CF2CF


3






0




S




(CH


2


)


2


CH


3








1004




N




CF


3






0




S




CH


3








1005




N




CF


3






0




S




CH


2


CH


3








1006




N




CF


3






0




S




(CH


2


)


2


CH


3








1007




N




CF


3






0




S




CHFCF


3








1008




N




CF


3






0




S




CH


2


CH


2


OH






1009




N




CF


3






0




S




CH


2


COOC(CH


3


)


3








1010




CH




CF


3






0




S




CH


3








1011




CH




CF


3






0




S




CH


2


CH


3








1012




CH




CF


3






0




S




(CH


2


)


2


CH


3








1013




CH




CF


3






0




S




CHO






1014




CH




CF


3






0




S




CHFCF


3








1015




CH




CF


3






0




S




CH


2


C≡CH






1016




CH




CF


3






0




S




COOCH


2


CH


3








1017




CH




CF


3






0




S




CH


2


COOC(CH


3


)


3








1018




CH




CF


3






0




S




CH


2


CN






















TABLE 4












































No.




X




Y




m




V




R


2






R


3






m.p.









1019




N




(CF


2


)


3


CHF


2






0




S




H




CH


2


CH


3









1020




N




CF


2


CF


2


CF


3






0




S




H




CH


2


CH


3








1021




N




CF


2


CF


3






0




S




H




CH


2


CH


3








1022




N




CH


2


CH


2


Cl




0




S




H




CH


2


CH


3








1023




N




CH


2


Cl




0




S




H




CH


2


CH


3








1024




N




CF


3






0




S




CH


2


CH


3






CH


2


CH


3








1025




N




CF


3






0




S




(CH


2


)


2


CH


3






H






1026




N




CF


3






0




S




CH(CH


3


)


2






H






1027




N




CF


3






0




S




CH


2


CH(CH


3


)


2






H






1028




N




CF


3






0




S




C(CH


3


)


3






H






1029




CH




CF


3






0




S




H




CH


3






oil






1030




CH




CF


3






0




S




H




CH


2


CH


3






oil






1031




CH




CF


3






0




S




H




C(CH


3


)


3






oil






1032




CH




CF


3






0




S




CH


2


CH


3






COOCH


2


CH


3








1033




CH




CF


3






0




S




(CH


2


)


2


CH


3






COOCH


2


CH


3








1034




CH




CF


3






0




S




CH(CH


3


)


2






COOCH


2


CH


3








1035




CH




CF


3






0




S




CH(CH


3


)


2






CONHCH


2


CH


3








1036




CH




CF


3






0




S




CH(CH


3


)


2






CONHCH


2


CH


3








1037




CH




CF


3






0




S




CH(CH


3


)


2






CON(CH


2


CH


3


)


2








1038




CH




CF


3






0




S




CH(CH


3


)


2






CONH-cyclo-C


3


H


7








1039




CH




CF


3






0




S




C(CH


3


)


3






COOCH


2


CH


3








1040




CH




CF


3






0




S




H




CONHCH


2


CH


3








1041




CH




CF


3






0




S




H




CON(CH


2


CH


3


)


2








1042




CH




CF


3






0




S




H




COOCH


2


CH


3






oil






1043




CH




CF


3






0




S




H




CH


2


COOCH


2


CH


3






oil






1044




CH




CF


3






0




S




H




CH


2


CHO






1045




CH




CF


3






0




S




H




CH


2


OCH


3








1046




CH




CF


3






0




S




H




CH


2


OCH


2


Ph






1047




CH




CF


3






0




S




H




H






1048




CH




CF


3






0




S




Cyclo-C


5


H


9






H






1049




CH




CF


3






0




S




CON(CH


3


)


2






CH


3






oil






1050




CH




CF


3






0




S




CH


3






CH


2


CH


2


OH






1051




CH




CF


3






0




S




CH


3






CH


2


CH


2


OCH


3








1052




CH




CF


3






0




S




CH


3






CH


2


CH


2


OCH


2


Ph






1053




CH




CF


3






0




S




CH


3






CH


2


CH


2


SPh






1054




CH




CF


3






0




S




CH


3






CH


3






oil






1055




CH




CF


3






0




S




CH


3






CH


2


CH


2


CHO






1055




CH




CF


3






0




S




CH


3






CH


2


CH


2


CHNPh






1057




CH




CF


3






0




S




CH


3






CH


2


CH


2


CONH


2








1058




CH




CF


3






0




S




H




(4-CF


3


O)C


6


H


4






120-121






1059




CH




CF


3






0




S




CH


2


C≡CH




H






1060




CH




CF


3






0




S




CH


2


CH


2


C≡CH




H






1061




CH




CF


3






0




S




CH


2


C≡CCH


2


CH


3






H






1062




CH




CF


3






0




S




CH


2


CH═C(CH


3


)


2






H






1063




CH




CF


3






0




S




CH


2


CH


2


CH═CH


2






H






1064




CH




CF


3






0




S




CH


2


CH═CH


2






H






1065




CH




CF


3






0




S




C(CH


3


)═CH


2






H






1066




CH




CF


3






0




S




CHFCF


3






H






1067




CH




CF


3






0




S




COOCH


2


CH


3






H






1068




CH




CF


3






0




S




CH


2


CH


2


OH




H






1069




CH




CF


3






0




S




CH


2


CH


2


OCH


3






H






1070




CH




CF


3






0




S




CH


2


COOC(CH


3


)


3






H






1071




CH




CF


3






0




S




CH


2


COCH


3






H






1072




CH




CF


3






0




S




COCH


3






H






1073




CH




CF


3






0




S




CH


2


OPh




H






1074




CH




CF


3






0




S




COPh




H






1075




CH




CF


3






0




S




CO(4-Cl)-C


6


H


4






H






1076




CH




CF


3






0




S




CF


2


CH


3






H






1077




CH




CF


3






0




S




CH


2


CN




H






1078




CH




CF


3






0




S




CH


2


CH


2


CN




H






1079




N




CF


3






0




S




H




H






1080




N




CF


3






0




S




H




CH


2


CH


2


CN






1081




N




CF


3






0




S




H




CH


2


CO


2


C(CH


3


)


3








1082




N




CF


3






0




S




H




CH


2


CHO






1083




N




CF


3






0




S




H




CH


2


CH


2


OH






1084




N




CF


3






0




S




H




CH


2


CH


2


OCH


3








1085




N




CF


3






0




S




Cyclo-C


5


H


9






H






1086




N




CF


3






0




S




CH


3






COOCH


2


CH


3








1087




N




CF


3






0




S




CH


3






COOH






1088




N




CF


3






0




S




CH


3






CONH


2








1089




N




CF


3






0




S




CH


3






CONHCH


2


CH


3








1090




N




CF


3






0




S




CH


3






CON(CH


2


CH


3


)


2








1091




N




CF


3






0




S




CH


3






CONHCH


3








1092




N




CF


3






0




S




CH


3






CONHCH


2


CN






1093




N




CF


3






0




S




CH


3






CON(CH


2


CN)


2








1094




N




CF


3






0




S




CH


3






CON(CH


3


)


2








1095




N




CF


3






0




S




CH


2


C≡CH




OCH


2


CH


3








1096




N




CF


3






0




S




CH


2


CH


2


C≡CH




OCH


2


CH


3








1097




N




CF


3






0




S




CH


2


C≡CCH


2


CH


3






OCH


2


CH


3








1098




N




CF


3






0




S




CH


2


CH═C(CH


3


)


2






OCH


2


CH


3








1099




N




CF


3






0




S




CH


2


CH


2


CH═CH


2






OCH


2


CH


3








1100




N




CF


3






0




S




CH


2


CH═CH


2






OCH


2


CH


3








1101




N




CF


3






0




S




C(CH


3


)═CH


2






OCH


2


CH


3








1102




N




CF


3






0




S




CHFCF


3






OCH


2


CH


3








1103




N




CF


3






0




S




COOCH


2


CH


3






OCH


2


CH


3








1104




N




CF


3






0




S




CH


2


CH


2


OH




OCH


2


CH


3








1105




N




CF


3






0




S




CH


2


CH


2


OCH


3






OCH


2


CH


3








1106




N




CF


3






0




S




CH


2


COOC(CH


3


)


3






OCH


2


CH


3








1107




N




CF


3






0




S




CH


2


COCH


3






H






1108




N




CF


3






0




S




COCH


3






H






1109




N




CF


3






0




S




CH


2


OPh




H






1110




N




CF


3






0




S




COPh




H






1111




N




CF


3






0




S




CO(4-Cl)-C


6


H


4






H






1112




N




CF


3






0




S




CF


2


CH


3






H






1113




N




CF


3






0




S




CH


2


CN




H






1114




N




CF


3






0




S




CH


2


CH


2


CN




H






1115




CH




CF


3






0




O




CH


2


CH


3






CH


2


CH


3








1116




CH




CF


3






0




O




(CH


2


)


2


CH


3






H






1117




CH




CF


3






0




O




H




CH


2


CH


3






oiI






1118




CH




CF


3






0




O




CH(CH


3


)


2






COOCH


2


CH


3








1119




CH




CF


3






0




O




CH(CH


3


)


2






COOH






1120




CH




CF


3






0




O




CH(CH


3


)


2






CONH


2








1121




CH




CF


3






0




O




CH(CH


3


)


2






CH


3








1122




CH




CF


3






0




O




C(CH


3


)


3






H






1123




CH




CF


3






0




O




H




CH


3








1124




CH




CF


3






0




O




H




cyclo-C


5


H


9








1125




CH




CF


3






0




O




H




CH


2


CH


2


CH


3








1126




CH




CF


3






0




O




H




Ph




103-10 






1127




CH




CF


3






0




O




H




2-Pyridyl






1128




CH




CF


3






0




O




H




2-Furyl






1129




CH




CF


3






0




O




Cyclo-C


5


H


9






H






1130




CH




CF


3






0




O




CH


3






COOCH


2


CH


3








1131




CH




CF


3






0




O




CH


3






COOH






1132




CH




CF


3






0




O




CH


3






CONH


2








1133




CH




CF


3






0




O




CH


3






CONHCH


2


CH


3








1134




CH




CF


3






0




O




CH


3






CON(CH


2


CH


3


)


2








1135




CH




CF


3






0




O




CH


3






CONHCH


3








1136




CH




CF


3






0




O




CH


3






CONHCH


2


CN






1137




CH




CF


3






0




O




CH


3






CON(CH


2


CN)


2








1138




CH




CF


3






0




O




CH


3






CON(CH


3


)


2








1139




CH




CF


3






0




O




CH


2


C≡CH




H






1140




CH




CF


3






0




O




CH


2


CH


2


C≡CH




H






1141




CH




CF


3






0




O




CH


2


C≡CCH


2


CH


3






H






1142




CH




CF


3






0




O




CH


2


CH═C(CH


3


)


2








1143




CH




CF


3






0




O




CH


2


CH


2


C═CH




H






1144




CH




CF


3






0




O




CH


2


CH═CH


2






H






1145




CH




CF


3






0




O




C(CH


3


)═CH


2






H






1146




CH




CF


3






0




O




CHFCF


3






H






1147




CH




CF


3






0




O




COOCH


2


CH


3






H






1148




CH




CF


3






0




O




CH


2


CH


2


OH




H






1149




CH




CF


3






0




O




CH


2


CH


2


OCH


3






H






1150




CH




CF


3






0




O




CH


2


COOC(CH


3


)


3






H






1151




CH




CF


3






0




O




CH


2


COCH


3






H






1152




CH




CF


3






0




O




COCH


3






H






1153




CH




CF


3






0




O




CH


2


Oph




H






1154




CH




CF


3






0




O




COPh




H






1155




CH




CF


3






0




O




CO(4-Cl)-C


6


H


4






H






1156




CH




CF


3






0




O




CF


2


CH


3






H






1157




CH




CF


3






0




O




CH


2


CN




H






1158




CH




CF


3






0




O




CH


2


CH


2


CN




H






1159




N




CF


3






0




O




CH


2


CH


3






CH


2


CH


3








1160




N




CF


3






0




O




(CH


2


)


2


CH


3






H






1161




N




CF


3






0




O




CH(CH


3


)


2






CONH


2








1162




N




CF


3






0




O




CH(CH


3


)


2






CH


3








1163




N




CF


3






0




O




C(CH


3


)


3






H






1164




N




CF


3






0




O




H




CH


3








1165




N




CF


3






0




O




H




CH


2


CH


3








1166




N




CF


3






0




O




H




CH


2


CH


2


CH


3








1167




N




CF


3






0




O




H




Ph






1168




N




CF


3






0




O




H




2-Pyridyl






1169




N




CF


3






0




O




H




2-Furyl






1170




N




CF


3






0




O




Cyclo-C


5


H


9






H






1171




N




CF


3






0




O




CH


3






COOCH


2


CH


3








1172




N




CF


3






0




O




CH


3






COOH






1173




N




CF


3






0




O




CH


3






CONH


2








1174




N




CF


3






0




O




CH


3






CONHCH


2


CH


3








1175




N




CF


3






0




O




CH


3






CON(CH


2


CH


3


)


2








1176




N




CF


3






0




O




CH


3






CONHCH


3








1177




N




CF


3






0




O




CH


3






CONHCH


2


CN






1178




N




CF


3






0




O




CH


3






CON(CH


2


CN)


2








1179




N




CF


3






0




O




CH


3






CON(CH


3


)


2








1180




N




CF


3






0




O




CH


2


C≡CH




H






1181




N




CF


3






0




O




CH


2


CH


2


C≡CH




H






1182




N




CF


3






0




O




CH


2


C≡CCH


2


CH


3






H






1183




N




CF


3






0




O




CH


2


CH≡C(CH


3


)


2






H






1184




N




CF


3






0




O




CH


2


CH


2


CH═CH


2






H






1185




N




CF


3






0




O




CH


2


CH═CH


2






H






1186




N




CF


3






0




O




C(CH


3


)═CH


2






H






1187




N




CF


3






0




O




CHFCF


3






H






1188




N




CF


3






0




O




COOCH


2


CH


3






H






1189




N




CF


3






0




O




CH


2


CH


2


OH




H






1190




N




CF


3






0




O




CH


2


CH


2


OCH


3






H






1191




N




CF


3






0




O




CH


2


COOC(CH


3


)


3






H






1192




N




CF


3






0




O




CH


2


COCH


3






H






1193




N




CF


3






0




O




COCH3




H






1194




N




CF


3






0




O




CH


2


Oph




H






1195




N




CF


3






0




O




COPh




H






1196




N




CF


3






0




O




CO(4-Cl)-C


6


H


4






H






1197




N




CF


3






0




O




CF


2


CH


3






H






1198




N




CF


3






0




O




CH


2


CN




H






1199




N




CF


3






0




O




CH


2


CH


2


CN




H






1200




N




CF


3






0




O




CH


2


NHSO


2


CH


3






CH


3








1201




N




CF


3






0




O




(CH


2


)


2


NHSO


2


CH


3






CH


3








1202




N




CF


3






0




O




CH


2


NHSO


2


CH


2


CH


3






CH


3








1203




N




CF


3






0




O




H




CH


2


NHSO


2


CH


2


Ph






1204




CH




CF


3






0




O




(CH


2


)


4


NHSO


2


CF


3






CH


3








1205




CH




CF


3






0




O




(CH


2


)


2


S(CH


2


)


2


CH


3






CH


2


CH


2


CH


3








1206




CH




CF


3






0




O




(CH


2


)


4


S(CH


2


)


4


OCH


3






CH


3








1207




CH




CF


3






0




S




CH


3






(CH


2


)


2


S(CH


2


)


2


CN






1208




CH




CF


3






0




S




CH


2


NHSO


2


CH


2


CH


3






CH


3








1209




CH




CF


3






0




S




CH


2


NHSO


2


CH


2


Ph




CH


2


CH


2


CH


3








1210




CH




CF


3






0




S




(CH


2


)


2


NHSO


2


CH


3






CF


3








1211




CH




CF


3






0




S




H




CH


2


NHSO


2


CH


3








1212




CH




CF


3






0




S




CH(CH


3


)CH


2


NHPh




CF


3








1213




CH




CF


3






0




S




(CH


2


)


2


S(2-F)-C


6


H


4






CH


2


CH


2


CH


3








1214




CH




CF


3






0




S




(CH


2


)


6


NHCH


2


)


6


OCH


3






CF


3








1215




CH




CF


3






0




S




H




(CH


2


)


2


NH-(2-F)-C


6


H


4








1216




CH




CF


3






0




S




(CH


2


)


3


NHCH


2


CN




H






1217




CH




CF


3






0




S




(CH


2


)


2


O(3-Cl)-C


6


H


4






CH


3








1218




CH




CF


3






0




S




CF


3






(CH


2


)


6


NHCH


2


CF


3








1219




CH




CF


3






0




S




CH


3






(CH


2


)


2


O(3-CH


3


)-C


6


H


4








1220




CH




CF


3






0




O




H




CH


2


NHPh






1221




CH




CF


3






0




O




CH


3






(CH


2


)


4


S(2-Br)-C


6


H


4








1222




CH




CF


3






0




O




(CH


2


)


6


NH(CH


2


)


2


OCH


3






CH


3








1223




CH




CF


3






0




O




(CH


2


)


2


NH(CH


2


)


4


OCH


3






H






1224




CH




CF


3






0




O




CF


3






(CH


2


)


3


NH-(4-CN)-C


6


H


4








1225




CH




CF


3






0




O




(CH


2


)


4


NHCH


2


CF


3






CH


3








1226




CH




CF


3






0




O




C


2


F


5






(CH


2


)


2


O(3-CH


3


)-C


6


H


4








1227




CH




CF


3






0




O




(CH


2


)


4


NHCH


2


CN




H






1228




CH




CF


3






0




O




(CH


2


)


3


O(4-Cl)-C


6


H


4






C


2


F


5
























TABLE 5













































No.




X




Y




V




R


4






R


5






R


6






R


7






m.p. [° C.]









1229




CH




CF


3






O




H




H




H




H




oil






1230




CH




CF


3






O




H




H




CH


3






H




oil






1231




CH




CF


3






O




H




H




CH


2


CH


3






H




oil






1232




CH




CF


3






O




H




H




CH(CH


3


)


2






H






1233




CH




CF


3






O




H




H




CH


2


CH(CH


3


)


2






H






1234




CH




CF


3






O




H




H




CH(CH


3


)CH


2


CH


3






H






1235




CH




CF


3






O




H




H




CH


2


OH




H






1236




CH




CF


3






O




H




H




CH(OH)CH


3






H






1237




CH




CF


3






O




H




H




CH


2


SH




H






1238




CH




CF


3






O




H




H




CH


2


CH


2


SCH


3






H






1239




CH




CF


3






O




H




H




(CH


2


)


3


NH


2






H






1240




CH




CF


3






O




H




H




(CH


2


)


4


NH


2






H






1241




CH




CF


3






O




H




H




CH═CH


2






H






1242




CH




CF


3






O




H




H




(CH


2


)


2


COOCH


3






H






1243




CH




CF


3






O




H




H




(CH


2


)


2


COOH




H






1244




CH




CF


3






O




H




H




(CH


2


)


2


CONH


2






H






1245




CH




CF


3






S




CH


3






CH


3






H




H






1246




CH




CF


3






O




H




H




CH


3






CH


3






oil






1247




CH




CF


3






O




H




H




CH


2


COOCH


3






H






1248




CH




CF


3






O




H




H




CH


2


COOH




H






1249




CH




CF


3






O




H




H




CH


2


CONH


2






H






1250




CH




CF


3






O




H




H




CH


2


Ph




H






1251




CH




CF


3






O




H




H




CH


2


-(4-OH)-C


6


H


4






H






1252




CH




CF


3






O




H




H




CH


2


-(3-Indolyl)




H






1253




CH




CF


3






O




CH


3






CH


3






H




H




oil






1254




CH




CF


3






O




CH


3






H




H




H




oil






1255




CH




CF


3






O




CH


3






H




H




Ph






1256




CH




CF


3






O




H





(CH


2


)


4






H






1257




CH




CF


3






NH




H





(CH


2


)


4






H






1258




CH




CF


3






NCH


3






H





(CH


2


)


4






H






1259




CH




CF


3






NCH


2


C


6


H


4






H





(CH


2


)


4






H






1260




CH




CF


3






NCH(CH


3


)


2






H





(CH


2


)


4






H






1261




CH




CF


3






O




Ph




H




Ph




H






1262




CH




CF


3






NH




Ph




H




Ph




H






1263




CH




CF


3






NCH


3






Ph




H




Ph




H






1264




CH




CF


3






NCH


2


C


6


H


4






Ph




H




Ph




H






1265




N




CF


3






O




H




H




CH


2


CH


3






H




oil






1266




N




CF


3






O




H




H




CH(CH


3


)


2






H






1267




N




CF


3






O




H




H




CH


2


CH(CH


3


)


2






H






1268




N




CF


3






O




H




H




CH


2


COOH




H






1269




N




CF


3






O




H




H




CH


2


COOCH


3






H






1270




N




CF


3






O




H




H




CH


2


CONH


2






H






1271




N




CF


3






O




CH


3






CH


3






H




H






1272




N




CF


3






O




H




(CH





H






1273




N




CF


3






O




H




H




CH


2


CH


2


SCH


3






H






1274




CH




CF


3






S




H




H




H




H




oil






















TABLE 6















































m.p.






No.




X




Y




R


8






R


1






[° C.]









1275




CH




CF


3






CH


3






SH




209-210






1276




CH




CF


3






CH


3






SCH


3








1277




CH




CF


3






CH


3






SCH


2


CH


3








1278




CH




CF


3






CH


3






S(CH


2


)


2


CH


3








1279




CH




CF


3






CH


3






SCH(CH


3


)


2








1280




CH




CF


3






CH


3






SPh






1281




CH




CF


3






CH


3






S(CH


2


)


3


CH


3








1282




CH




CF


3






CH


3






SCH(CH


3


)CH


2


CH


3








1283




CH




CF


3






CH


3






SCH


2


CH(CH


3


)


2








1284




CH




CF


3






CH


3






OH




119-120






1285




CH




CF


3






CH


3






OCH


3








1286




CH




CF


3






CH


3






OCH


2


CH


3








1287




CH




CF


3






CH


3






OC HF


2








1288




CH




CF


3






CH


3






OCH


2


Ph






1289




CH




CF


3






CH


3






OCONHPh






1290




CH




CF


3






CH


3






OCONH-(4-F)-C


6


H


4








1291




CH




CF


3






CH


3






OCONH-(3,5-di-Cl)-C


6


H


3








1292




CH




CF


3






CH


2


CN




OCH


3








1293




CH




CF


3






CH


2


CN




OCH


2


CH


3








1294




CH




CF


3






CH


2


CN




OCHF


2








1295




CH




CF


3






CH


2


CN




OCH


2


Ph






1296




CH




CF


3






CH


2


CN




OCONHPh






1297




CH




CF


3






CH


2


CN




OCONH-(4-F)-C


8


H


4








1298




CH




CF


3






CH


2


OCH


2


CH


3






OCH


3








1299




CH




CF


3






CH


2


OCH


2


CH


3






OCH


2


CH


3








1300




CH




CF


3






CH


2


OCH


2


CH


3






OCHF


2








1301




CH




CF


3






CH


2


OCH


2


CH


3






OCH


2


Ph






1302




CH




CF


3






CH


2


OCH


2


CH


3






OCONHPh






1303




CH




CF


3






H




CH


3






203-204






1304




CH




CF


3






H




CH


2


CH


3






134-135






1305




CH




CF


3






H




(CH


2


)


2


CH


3








1306




CH




CF


3






H




CH(CH


3


)


2








1307




CH




CF


3






H




Cyclo-C


3


H


5








1308




CH




CF


3






H




(CH


2


)


3


CH


3








1309




CH




CF


3






H




CH(CH


3


)CH


2


CH


3








1310




CH




CF


3






H




CH


2


CH(CH


3


)


2








1311




CH




CF


3






H




CH═CH


2








1312




CH




CF


3






H




CH


2


CH═C(CH


3


)


2








1313




CH




CF


3






H




CH


2


CH


2


CH═CH


2








1314




CH




CF


3






H




CH


2


CH═CH


2








1315




CH




CF


3






H




C(CH


3


)═CH


2








1316




CH




CF


3






H




CHFCF


3








1317




CH




CF


3






H




COOCH


2


CH


3








1318




CH




CF


3






H




CH


2


CH


2


OH






1319




CH




CF


3






H




CH


2


CH


2


OCH


3








1320




CH




CF


3






H




CH


2


COOC(CH


3


)


3








1321




CH




CF


3






CH


3






CH


2


COOC(CH


3


)


3








1322




CH




CF


3






CH


2


CN




CH


2


COOC(CH


3


)


3








1323




CH




CF


3






CH


2


OCH


2


CH


3






CH


2


COOC(CH


3


)


3








1324




CH




CF


3






H




CH


2


SPh






1325




CH




CF


3






H




CH


2


CONHCH


3








1326




CH




CF


3






H




CH


2


COCH


3








1327




CH




CF


3






H




COCH3






1328




CH




CF


3






H




CH


2


Oph






1329




CH




CF


3






H




COPh






1330




CH




CF


3






H




CO(3-Cl)-C


6


H


4








1331




CH




CF


3






H




CF


2


CH


3








1332




CH




CF


3






H




CH


2


CN






1333




CH




CF


3






H




CH


2


CH


2


CN






1334




CH




CF


3






H




CH


2


CH(—O—)CH


2








1336




CH




CF


3






H




CH


2


(4-OCH


3


)Ph






1337




N




CF


3






CH


3






SH






1338




N




CF


3






CH


3






SCH


3








1339




N




CF


3






CH


3






SCH


2


CH


3








1340




N




CF


3






CH


3






SPh






1341




N




CF


3






CH


3






SCH


2


CH(CH


3


)


2








1342




N




CF


3






CH


3






OH






1343




N




CF


3






CH


3






OCH


3








1344




N




CF


3






CH


3






OCH


2


CH


3








1345




N




CF


3






CH


3






OCH


2


Ph






1346




N




CF


3






CH


3






OCONHPh






1347




N




CF


3






CH


2


CN




OCH


3








1348




N




CF


3






CH


2


CN




OCH


2


CH


3








1349




N




CF


3






CH


2


CN




OCH


2


Ph






1350




N




CF


3






CH


2


CN




OCONHPh






1351




N




CF


3






CH


2


OCH


2


CH


3






OCH


3








1352




N




CF


3






CH


2


OCH


2


CH


3






OCH


2


Ph






1353




N




CF


3






CH


2


OCH


2


CH


3






OCONHPh






1354




N




CF


3






H




CH


3








1355




N




CF


3






H




CH


2


CH


3








1356




N




CF


3






H




(CH


2


)


2


CH


3








1357




N




CF


3






H




CH(CH


3


)


2








1358




N




CF


3






H




(CH


2


)


3


CH


3








1359




N




CF


3






H




CH(CH


3


)CH


2


CH


3








1360




N




CF


3






H




CH


2


CH(CH


3


)


2








1361




N




CF


3






H




CH


2


C═C(CH


3


)


2








1362




N




CF


3






H




CH


2


CH═CH


2








1363




N




CF


3






H




C(CH


3


)H═CH


2








1364




N




CF


3






H




COOCH


2


CH


3








1365




N




CF


3






H




CH


2


CH


2


OH






1366




N




CF


3






H




CH


2


CH


2


OCH


3








1367




N




CF


3






H




CH


2


COOC(CH


3


)


3








1368




N




CF


3






H




CH


2


SPh






1369




N




CF


3






H




CH


2


CONHCH


3








1370




N




CF


3






H




CH


2


COCH


3








1371




N




CF


3






H




COCH3






1372




N




CF


3






H




CH


2


Oph






1373




N




CF


3






H




COPh






1374




N




CF


3






H




CH


2


CN






1375




N




CF


3






H




CH


2


CH


2


CN






1376




CH




CF


3






CH


3






CH


2


CH


3






oil














C. BIOLOGICAL EXAMPLES




Example 1




A Petri dish whose bottom is covered with filter paper and which contains about 5 ml of culture medium is prepared. Pieces of filter paper with about 30, 24-hour-old eggs of the American tobacco budworm (


Heliothis virescens


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




Example 2




Germinated broad bean seeds (


Vicia faba


) with radicles are transferred into brown glass bottles filled with tap water and subsequently populated with approximately 100 black bean aphids (


Aphis fabae


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




Example 3




The leaves of 12 rice plants having a stem length of 8 cm are dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has dripped off, the rice plants treated in this manner are placed in a Petri dish and populated with approximately 20 larvae (L3 stage) of the rice leaf hopper species


Nilaparvata lugens.


The Petri dish is closed and stored in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity). After 6 days' storage, the mortality among the leaf hopper larvae is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Example Nos. 88, 139 and 927 effect a mortality of 90-100%.




Example 4




Germinated broad bean seeds (


Vicia faba


) with radicles are transferred into brown glass bottles filled with tap water. Four milliliters of an aqueous solution of the formulated preparation to be examined are pipetted into the brown glass bottle. The broad bean is subsequently heavily populated with approximately 100 black bean aphids (


Aphis fabae


). Plant and animals are then stored in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity). After 3 and 6 days' storage, the root-systemic activity of the preparation on the aphids is determined. At a concentration of of 30 ppm (based on the content of active compound), the Preparations of Example Nos. 78, 79, 80, 81, 83, 84, 88, 133, 135, 136, 137, 138, 139, 187, 1117, 1229, 1230, 1231, 1246 and 1254 effect a mortality of 90-100% among the aphids by root-systemic action.



Claims
  • 1. A 4-haloalkyl-3-heterocyclylpyridine of the formula I if desired in the form of its salt wherein Y is halo-C1-C8-alkyl; X is CH; m is 0 or 1; Q is a 5-membered heterocyclic group in which a) X1=W, X2=NRa, X3=CRbR1 or b) X1=NRa, X2=CRbR1, X3=W or c) X1=O, X2=CRaR1, X3=NRb or d) X1=S, X2=CRaR1, X3=NRb or e) X1=V, X2=CRaR2, X3=CRbR3 or f) X1=V, X2=CR4R5, X3=CR6R7; Ra and Rb together are a bond V is oxygen, sulfur or NH9; W is oxygen or sulfur; R1 is hydrogen, (C1-C20)-alkyl, (C2-C20)-alkenyl, (C2-C20)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C6-C8)-cycloalkynyl, where the six last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, —C(═W)R10, —C(═NOR10)R10, —C(═NNR102)R10, —C(═W)OR10, —C(═W)NR102, —OC(═W)R10, —OC(═W)OR10, —NR10C(═W)R10, —N[C(═W)R10]2, —NR10C(═W)OR10, —C(═W)NR10—NR102, —C(═W)NR10—NR10[C(═W)R10], —NR10—C(═W)NR102, NR10—NR10C(═W)R10, —NR10—N[C(═W)R10]2, —N[(C═W)R10]—NR102, —NR10—NR10[(C═W)R10], —NR10—NR10[(C═W)WR10], —NR10—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 (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, 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, where these six abovementioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, —C(═W)R10, —C(═W)OR10, —C(═W)NR102, —OR10, —NR102, —SR10, —SOR10 and —SO2R10; 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, heterocyclyl, 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, where the six abovementioned radicals are optionally substituted by one or more radicals from the group cyano, nitro, halogen, —C(═W)R10, —C(═W)OR10, —C(═W)NR102, —NR10C(═W)R10, —N[C(═W)R10]2, —OC(═W)R10, —OC(═W)OR10, —OR10, —NR102, —SR10, —SOR10 and —SO2R10; 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; R2 and R3 independently of one another have the definitions given in R1; 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; 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; R5 and R7 independently of one another are hydrogen, (C1-C20)-alkyl, (C2-C20)-alkenyl, (C2-C20)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C6-8)-cycloalkynyl, where the six last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, —C(═W)R10, —C(═NOR10)R10, —C(═NNR102)R10, —C(═W)OR10, —C(═W)NR102, —OC(═W)R10, —OC(═W)OR10, —NR10C(═W)R10, —N[C(═W)R10]2, —NR10C(═W)OR10, —C(═W)NR10—NR102, —C(═W)NR10—NR10[C(═W)R10], —NR10—C(═W)NR102, —NR10—NR10C(═W)R10, —NR10—N[C(═W)R10]2, —N[(C═W)R10]—NR102, —NR10—NR10[(C═W)R10], —NR10—NR10[(C═W)WR10, —NR10—NR10[(C═W)NR102], —NR10(C═NR10)R10, —NR10(C═NR10)NR102, —O—NR102, —O—NR10(C═W)R10, —OR10, —NR102, —SR10, —SiR103, —SeR10, —PR102, —P(═W)R102, —SOR10, —SO2R10, —PW2R102, —PW3R102, aryl and heterocylyl, of which the two mentioned last are 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, (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, 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, where these six abovementioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, —C(═W)R10, —C(═W)OR10, —C(═W)NR102, —OR10, —NR102, —SR10, —SOR10 and —SO2R10, 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, which is optionally substituted by one or more radicals from the group (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycoalkyl, (C4-C8)-cycloalkenyl and (C6-C8)-cycloalkynyl, where the six abovementioned radicals are optionally substituted by one or more radicals from the group cyano, nitro, halogen, —C(═W)R10, —C(═W)OR10, —C(═W)NR102, —OR10, —NR102, —SR10, —SOR10 and —SO2R10, halogen, cyano, nitro, —C(═W)R10, —C(═W)OR10, —C(═W)NR102, —OC(═W)R10, —OR10, —NR102, —SR10, —SOR10 and —SO2R10, —C(═W)R10, —C(═NOR10)R10, —C(═NNR102)R10, —C(═W)OR10, —C(═W)NR102 or halogen; 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; R6 and R7 together form one of the groups ═O, ═S or ═N—R9; 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-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)-halocycloalkylthio, (C4-C8)-halocycloalkenylthio, (C3-C8)-cycloalkyl-(C1-C4)-alkylthio, (C4-C8)-cycloalkenyl-(C1-C4)-alkylthio, (C3-C8)-cycloalkyl-(C2-C4)-alkenylthio, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylthio, (C1-C6)-alkyl-(C3-C8)-cycloalkylthio, (C2-C6)-alkenyl-(C3-C8)-cycloalkylthio, (C2-C6)-alkynyl-(C3-C8)-cycloalkylthio, (C1-C6)-alkyl-(C4-C8)-cycloalkenylthio, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylthio, (C1-C6)-alkylsulfinyl, (C2-C6)-alkenylsulfinyl, (C2-C6)-alkynylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C2-C6)-haloalkenylsulfinyl, (C2-C6)-haloalkynylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C4-C8)-cycloalkenylsulfinyl, (C3-C8)-halocycloalksulfinyl, (C4-C8)-halocycloalkenylsulfinyl, (C3-C8)-cycloalkyl-(C1-C4)-alkylsufinyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkylsulfinyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenylsulfinyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylsulfinyl, (C1-C6)-alkyl-(C3-C8)-cycloalkylsulfinyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkylsulfinyl, (C2-C6)-alkynyl-(C3-C8)-cycloalkylsulfinyl, (C1-C6)-alkyl-(C4-C8)-cycloalkenylsulfinyl, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylsulfinyl, (C1-C6)-alkylsulfonyl, (C2-C6)-alkenylsulfonyl, (C2-C6)-alkynylsulfonyl, (C1-C6)-haloalkylsulfonyl, (C2-C6)-haloalkenylsulfonyl, (C2-C6)-haloalkynylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C4-C8)-cycloalkenylsulfonyl, (C3-8)-halocycloalkylsulfonyl, (C4-C8)-halocycloalkenylsulfonyl, (C3-C8)-cycloalkyl-(C1-C4)-alkylsulfonyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkylsulfonyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenylsulfonyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylsulfonyl, (C1-C6)-alkyl-(C3-C8)-cycloalkylsulfonyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkylsulfonyl, (C2-C6)-alkynyl-(C3-C8)-cycloalkylsulfonyl, (C1-C6)-alkyl-(C4-C8)-cycloalkenylsulfonyl, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylsulfonyl, (C1-C6)-alkylamino, (C2-C6)-alkenylamino, (C2-C6)-alkynylamino, (C1-C6)-haloalkylamino, (C2-C6)-haloalkenylamino, (C2-C6)-haloalkynylamino, (C3-C8)-cycloalkylamino, (C4-C8)-cycloalkenylamino, (C3-C8)-halocycloalkamino, (C4-C8)-halocycloalkenylamino, (C3-C8)-cycloalkyl-(C1-C4)-alkylamino, (C4-C8)-cycloalkenyl-(C1-C4)-alkylamino, (C3-C8)-cycloalkyl-(C2-C4)-alkenylamino, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylamino, (C1-C6)-alkyl-(C3-C8)-cycloalkylamino, (C2-C6)-alkenyl-(C3-C8)-cycloalkylamino, (C2-C6)-alkynyl-(C3-C8)-cycloalkylamino, (C1-C6)-alkyl-(C4-C8)-cycloalkenylamino, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylamino, (C1-C6)-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, arylcarbamoyl, aroyl, aroyloxy, aryloxycarbonyl, aryl-(C1-C4)-alkoxy, aryl-(C2-C4)-alkenyloxy, aryl-(C1-C4)-alkylthio, aryl-(C2-C4)-alkenylthio, aryl-(C1-C4)-alkylamino, aryl-(C2-C4)-alkenylamino, aryl-(C1-C6)-dialkylsilyl, diaryl-(C1-C6)-alkylsilyl, triarylsilyl and 5 or 6-membered heterocyclyl; 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, (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)-halocydoalkamino and (C4-C8)-halocycloalkenylamino; —C(═W)R11, OR11 or NR112; R9 is (C1-C8)-alkyl, (C2-C6)-alkenyl, (C2C6)-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; 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, (C38)-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)-cycloalkyl-(C2-C4)-alkenylsulfinyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkenylsulfinyl, (C1-C6)-alkyl-(C3-C8)-cycloalkylsulfinyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkylsulfinyl, (C2-C6)-alkynyl-(C3-C6)-cycloalkylsulfinyl, (C1-C8)-alkyl-(C4-C8)-cycloalkenyl-sulfinyl, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylsulfinyl, (C1-C6)-alkylsulfonyl, (C2-C6)-alkenylsulfonyl, (C2-C6)-alkynylsulfonyl, (C1-C6)-haloalkylsulfonyl, (C2-C6)-haloalkenylsulfonyl, (C2-C6)-haloalkynylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C4-C8)-cycloalkenylsulfonyl, (C3-C8)-halocycloalksulfonyl, (C4-C8)-halocycloalkenylsulfonyl, (C3-C8)-cycloalkyl-(C1-C4)-alkylsulfonyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkylsulfonyl, (C3-C8)-cycloalkyl-(C2-C4)-alkenylsulfonyl, (C4-C8)-cycloalkenyl(C1-C4)-alkenylsulfonyl, (C1-C6)-alkyl-(C3-C8)-cycloalkylsulfonyl, (C2-C6)-alkenyl-(C3-C8)-cycloalkylsulfonyl, (C2-C6)-alkynyl-(C3-C8)-cycloalkylsulfonyl, (C1-C6)-alkyl-(C4-C8)-cycloalkenylsulfonyl, (C2-C6)-alkenyl-(C4-C8)-cycloalkenylsulfonyl, (C1-C6)-alkylamino, (C2-C6)-alkenylamino, (C2-C6)-alkynylamino; (C1-C6)-haloalkylamino, (C2-C6)-haloalkenylamino, (C2-C6)-haloalkynylamino, (C3-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-C4)-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-(C2-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-C4)-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; 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)-akylthio, (C2-C6)-alkenylthio, (C2-C6)-alkynylthio, (C1-C6)-haloalkylthio, (C2-C6)-haloalkenylthio, (C2-C6)-haloalkynylthio, (C3-C8)-cyclalkylthio, (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)-halocycloalkylsulfonyl, (C4-C8)-halocycloalkenylsulfonyl, (C1-C6)-alkylamino, (C2-C6)-alkenylamino, (C2-C6)-alkynylamino, (C1-C6)-haloalkylamino, (C2-C6)-haloalkenylamino, (C2-C6)-haloalkynylamino, (C3-C8)-cycloalkylamino, (C4-C8)-cycloalkenylamino, (C3-C8)-halocycloalkamino and (C4-C8)-halocycloalkenylamino; 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 with the proviso that the compounds listed below are not included:3-(2-chlorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole 3-(2,6-difluorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole 3-(2-chloro-4-fluorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole 3-(3,5-dichlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(4-trifluoromethyl-3-pyridyl)-3-phenyl-1,2,4-oxadiazole 3-(4-trifluoromethyl-3-pyridyl)-5-phenyl-1,2,4-oxadiazole 5-(2-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(3-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(4-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(2-fluorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(4-fluorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(2,4-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(3,4-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(3,5-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(2,6-dichloro-4-pyridyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(3,5-bistrifluoromethylphenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 2-(2-chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole 2-(3-chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole 2-(4-chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole 2-(2-trifluoromethoxyphenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole 2-(4-trifluoromethoxyphenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole 2-(4-trifluoromethyl-3-pyridyl)-5-phenyl-1,3,4-oxadiazole 2-(4-trifluoromethyl-3-pyridyl)-4-methylthiazolecarbohydrazide ethyl 2-(4-trifluoromethyl-3-pyridyl)-4-methylthiazolecarboxylate N-(4-chlorophenyl)carbonyl-N′-[2-(4-trifluoromethyl-3-pyridyl)-4-methyl-5-thiazolyl]carbonylhydrazine 2-(4-trifluoromethyl-3-pyridyl)-4-thiazolecarbohydrazide 4-(4chlorophenyl)-2-(4-trifluoromethyl-3-pyridyl)thiazole 4-(4-cyanophenyl)-2-(4-trifluoromethyl-3-pyridyl)thiazole N-(4-trifluoromethylphenyl)carbonyl-N′-[2-(4-trifluoromethyl-3-pyridyl)-4-thiazolyl]carbonylhydrazine 2-(2-(4-trifluoromethyl-3-pyridyl)thiazolyl)-5-chloro-3-methylbenzo[b]thiophene.
  • 2. A 4-haloalkyl-3-heterocyclylpyrineor 4-haloalkyl-5-heterocyclylpyrimidine as claimed in claim 1, whereinY is C1-C6-alkyl which is mono- or polysubstituted by chlorine and/or fluorine; m is zero; Q is a 5-membered heterocyclic group in which a) X2=NRa and X3=CRbR1 or b) X2=CRaR2 and X3=CRbR3 or c) X2=CR4R5 and X3=CR6R7; Ra and Rb together are a bond; 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 A1consisting 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; 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, fluorine, chlorine, bromine, 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; 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.
  • 3. A 4-haloalkyl-3-heterocyclylpyridine or 4-haloalkyl-5-heterocyclylpyrimidine as claimed in claim 1, whereinY is trifluoromethyl; 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; 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; 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.
  • 4. A 4-haloalkyl-3-heterocyclylpyridine or 4-haloalkyl-5-heterocyclyl-pyrimidine as claimed in claim 1, whereinR1, R2, R3, R4 and R5 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; 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.
  • 5. A process for preparing compounds of the formula I as claimed in claim 1, which comprises reacting, ifA) X1=O, X2=NRa, X3=CRbR1 activated derivatives of the acid of the formula (II), where X and Y are as defined above, in the presence of a base with a compound of the formula (III), in which the radical R1 is as defined in formula (I), or, ifB) X1=S, X2=NRa, X3=CRbR1 compounds of the formula (VII) with an electrophilic amination agent or, ifC) X1=NRa, X2=CRbR1, X3=O amidoximes of the formula (V) with activated derivatives of acids of the formula (VI) or with the acids of the formula (VI) themselves or, ifD) X1=S, X2=CRaR1, X3=NRb N,N′-diacylhydrazines of the formula (XIII) with a thiolation agent, such as Lawessons reagent, in an inert solvent or, ifE) X1=O, X2=CRaR1, X3=NRb acids of the formula (i) with hydrazides of the formula (X), in which R1 is as defined above using an activating reagent, such as phosphorus oxychloride or phosphorus pentachloride, or acid hydrazides of the formula (XI) with orthoesters of the formula (XII), where R1 is as defined above, and R12 is (C1-C4)-alkyl or, ifF) X1=O, X2=CRaR2, X3=CRbR3 and Ra, Rb and R3 are as defined above, compounds of the formula (XIV) with a dehydrating reagent, such as inorganic acid chlorides, inorganic acids and anhydrides, or, ifG) X1=S, X2=CRaR2, X3=CRbR3 thioamides of the formula (XVII) with carbonyl derivatives of the formula (XVIII) where Z is halogen, in particular chlorine or bromine, acycloxy or sulfonyloxy, in particular methanesulfonyloxy or tolylsulfonyloxy or, ifH) X1=S, X2=CR4R5, X3=CR6R7 thioamides of the formula (XVII) with compounds of the formula (XIX) where the two substituents Z are as defined above and may either be identical or different or, ifI) X1=NRa, X2=CRbR1, X3=NR8 and Ra, Rb, R1 and R8 are as defined above, hydrazides of the formula (XX) with a compound of the formula (XXI) or with thioamides of the formula (XXII),
  • 6. A composition having insecticidal, acaricidal and/or nematicidal action, which comprises an effective amount at least one compound as claimed in claim 1.
  • 7. A composition having insecticidal, acaricidal and nematicidal action as claimed in claim 6 in a mixture with carriers and/or surfactants.
  • 8. A composition as claimed in claim 6, which contains an effective amount of a further active compound from the group acaricides, fungicides, herbicides, insecticides, nematicides or growth-regulating substances.
  • 9. The method of controlling endo- and ectoparasites which comprises applying an effective amount of the compound of claim 1.
  • 10. A method for controlling harmful insects, acarina and nematodes, which comprises applying an effective amount of a compound as claimed in claim 1 or of a composition as claimed in claim 6 to the area where the action is desired.
  • 11. A process for protecting useful plants against the undesired action of harmful insects, acarina and nematodes, which comprises using at least one of the compounds as claimed in claim 1 for treating the seed of the useful plants.
  • 12. The method of controlling end- and ectoparasites which comprises applying an effective amount of the composition as claimed in claim 6.
Priority Claims (1)
Number Date Country Kind
197 25 450 Jun 1997 DE
US Referenced Citations (4)
Number Name Date Kind
4788210 Luethy et al. Nov 1988
5571815 Schaper et al. Nov 1996
5633267 Heinemann et al. May 1997
5723450 Reuschling et al. Mar 1998
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Number Date Country
4239727 A1 Jun 1994 DE
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0371925 A2 Jun 1990 EP
WO 9319050 Sep 1993 WO
WO 9507891 Mar 1995 WO
9507891 Mar 1995 WO
Non-Patent Literature Citations (1)
Entry
Maybridge Catalog 1996/1997 (Maybridge Chemical Company, Ltd.).