Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-05-31
2004-01-06
Qazi, Sabiha (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S363000, C548S100000, C548S125000, C548S128000
Reexamination Certificate
active
06673820
ABSTRACT:
The present invention relates to novel substituted aminoheterocyclylamides of the formula
in which
R
1
is hydrogen, halogen, C
1
-C
6
alkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkyl or unsubstituted or mono- to pentasubstituted phenyl, where the substituents are selected from the group consisting of C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, aryloxy, halogen, cyano and nitro, where, if the number of substituents exceeds 1, the substituents can be identical or different;
R
2
is hydrogen, C
1
-C
6
alkyl, (C
1
-C
6
alkylene)phenyl, pyridyl, COOR
6
, CONR
7
R
8
, COR
6
, allyl or CH
2
—O—R
6
;
R
3
is unsubstituted or substituted heterocyclyl, where the substituents are in each case selected from the group consisting of unsubstituted or substituted phenyl, where the substituents are selected from the group consisting of C
1
-C
6
alkyl, C
1
-C
6
alkoxy, halogen, cyano and nitro, where, if the number of substituents exceeds 1, the substituents can be identical or different, benzyl, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, aryloxy, halogen, cyano, hydroxyl, amino and nitro, where, if the number of substituents exceeds 1, the substituents can be identical or different;
R
6
is C
1
-C
6
alkyl, phenyl or benzyl;
R
7
and R
8
independently of one another are hydrogen or C
1
-C
6
alkyl;
X
1
is N or C(CN);
X
2
is N, C(CN), C(COOR
6
), C(COR
6
), C(SOR
6
), C(CONR
7
R
8
) or C(NO
2
); and
X
3
is O or S;
to their preparation and to their use for controlling pests, and furthermore to pesticides comprising at least one of these compounds.
Substituted aminoheterocyclylamides having pesticidal action are described, for example, in DE 197 27 162. However, the active compounds actually disclosed in this publication cannot always meet the requirements with respect to activity efficacy and spectrum. Accordingly, there is a need for active compounds having improved pesticidal properties. It has now been found that the aminoheterocyclylamides of the formula I have excellent pesticidal properties, in particular against endoparasites.
The alkyl groups mentioned in the definitions of substituents can be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl and hexyl, and their branched isomers.
Corresponding alkylene groups can likewise be straight-chain or branched and are, for example, methylene, ethylene, n-propylene, isopropylene, n-butylene, sec-butylene, isobutylene, tert-butylene, pentylene and hexylene, and their branched isomers.
Halogen is generally fluorine, chlorine, bromine or iodine. This also applies to halogen in combination with other meanings, such as haloalkyl or halophenyl.
Haloalkyl groups preferably have a chain length of from 1 to 6 carbon atoms. Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl.
Alkoxy groups preferably have a chain length of from 1 to 6 carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy, and the isomers pentyloxy and hexyloxy; preferably methoxy and ethoxy.
Aryloxy is phenoxy or naphthyloxy, preferably phenoxy.
Heterocyclyl is an aromatic 5- or 6-membered cyclic group which may be benzo-fused and which contains at least one heteroatom selected from the group consisting of oxygen, nitrogen and sulfur. Typical representatives are, for example, pyridyl, pyrryl, furyl, thienyl, imidazolyl, pyrazolyl, benzofuryl, benzothienyl, isoxazolyl, oxazolyl, thiazolyl and indolyl.
Preferred compounds of the formula I are those in which
R
1
is halogen, C
1
-C
6
alkoxy, C
1
-C
6
haloalkyl or phenyl;
R
2
is hydrogen, C
1
-C
6
alkyl, (C
1
-C
6
alkylene)phenyl or pyridyl;
R
3
is unsubstituted or substituted heterocyclyl, where the substituents are in each case selected from the group consisting of unsubstituted or substituted phenyl, where the substituents are selected from the group consisting of C
1
-C
6
alkoxy, halogen, cyano and nitro, where, if the number of substituents exceeds 1, the substituents can be identical or different, benzyl, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, aryloxy, halogen, cyano, hydroxyl, amino and nitro, where, if the number of substituents exceeds 1, the substituents can be identical or different;
X
1
is N or C(CN);
X
2
is N or C(CN); and
X
3
is O or S.
Particularly preferred embodiments of the compounds of the formula I are:
(1) a compound of the formula I in which R
1
is halogen, C
1
-C
6
haloalkyl or phenyl; preferably fluorine, chlorine, C
1
-C
4
haloalkyl or phenyl; particularly preferably chlorine, C
1
-C
2
haloalkyl or phenyl; very particularly preferably chlorine, trichloromethyl or phenyl;
(2) a compound of the formula I in which R
2
is hydrogen, C
1
-C
4
alkyl or (C
1
-C
4
alkylene)phenyl; preferably hydrogen or (C
1
-C
2
alkylene)phenyl; particularly preferably hydrogen;
(3) a compound of the formula I in which R
3
is unsubstituted or substituted pyrazolyl or unsubstituted or substituted pyridyl, where the substituents are in each case selected from the group consisting of unsubstituted or substituted phenyl, where the substituents are selected from the group consisting of C
1
-C
6
alkoxy, halogen, cyano and nitro, where, if the number of substituents exceeds 1, the substituents can be identical or different, benzyl, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, aryloxy, halogen, cyano, hydroxyl, amino and nitro, where, if the number of substituents exceeds 1, the substituents can be identical or different;
preferably substituted pyrazolyl or substituted pyridyl, where the substituents are in each case selected from the group consisting of substituted phenyl, where the substituents are selected from the group consisting of C
1
-C
2
alkoxy, halogen and nitro, where, if the number of substituents exceeds 1, the substituents can be identical or different, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, halogen and nitro, where, if the number of substituents exceeds 1, the substituents can be identical or different; particularly preferably substituted pyrazolyl, where the substituents are selected from the group consisting of substituted phenyl, where the substituents are selected from the group consisting of methoxy, chlorine, fluorine and nitro, where, if the number of substituents exceeds 1, the substituents can be identical or different, C
1
-C
4
alkyl, C
1
-C
2
haloalkyl, chlorine and fluorine, where, if the number of substituents exceeds 1, the substituents can be identical or different; very particularly preferably substituted pyrazolyl, where the substituents are selected from the group consisting of substituted phenyl, where the substituents are selected from the group consisting of methoxy, chlorine and fluorine, where, if the number of substituents exceeds 1, the substituents can be identical or different, C
1
-C
2
alkyl and C
1
-C
2
haloalkyl, where, if the number of substituents exceeds 1, the substituents can be identical or different;
(4) a compound of the formula I in which X
1
and X
2
are N;
(5) a compound of the formula I in which X
3
is O;
(6) a compound of the formula I in which R
1
is halogen, C
1
-C
6
haloalkyl or phenyl; R
2
is hydrogen, C
1
-C
4
alkyl or (C
1
-C
4
alkylene)phenyl; R
3
is substituted pyrazolyl or substituted pyridyl, where the substituents are in each case selected from the group consisting of substituted phenyl, where the substituents are selected from the group consisting of C
1
-C
2
alkoxy, halogen and nitro, where, if the number of substituents exceeds 1, the substituents can be identical or different, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, halogen and nitro, where, if the number of substituents exceeds 1, the substituents can be identical or differ
Bouvier Jacques
Ducray Pierre
Schwarzenbach Maurizio
Kung John W.
Lee Michael U.
Novartis Animal Health US Inc.
Qazi Sabiha
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