Pesticidal aminoheterocyclamide compounds

Details Pesticidal aminoheterocyclamide compounds Pesticidal aminoheterocyclamide compounds

2002-05-16

2003-12-23

Pryor, Alton N. (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S345000, C514S349000, C514S351000, C514S352000, C544S242000, C544S298000, C544S322000, C546S001000, C546S250000, C546S252000, C546S268100, C546S268700, C546S269700, C546S271100, C546S272400

Reexamination Certificate

active

06667326

ABSTRACT:

The present invention relates to new substituted aminoheterocyclylamides of formula
wherein
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 penta-substituted phenyl, whereby the substituents are selected from the group comprising C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, aryloxy, halogen, cyano and nitro, whereby if the number of substituents is greater than 1, the substituents may 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
;
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
);
X
3
is O or S;
Q is CH or N;
R
3
and R
4
, independently of one another, are hydrogen, C
1
-C
6
-alkyl or together with the C-atom to which they are bonded, a C
3
-C
7
-cycloalkyl ring;
R
5
is a substituent from the group comprising C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6-
alkinyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, aryloxy, halogen, cyano, hydroxy, amino, nitro and mono- to penta-substituted phenyl, whereby the substituents are selected from the group comprising C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkinyl, C
1
-C
6
-haloalkyl, C
1
-C
6
alkoxy, aryloxy, halogen, cyano, hydroxy, amino and nitro, and if the number of phenyl substituents is greater than 1, they may be identical or different, whereby if m is greater than 1, the substituents R
5
may 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;
m is 1, 2 or 3; and
n is 0 or 1;
the preparation thereof and the use thereof in the control of pests, and also pesticides containing at least one of these compounds.
Substituted aminoheterocyclylamides having pesticidal activity are described for example in DE 197 27 162. However, the active ingredients specifically disclosed therein cannot always fulfil the requirements regarding potency and activity spectrum. There is therefore a need for active ingredients with improved pesticidal properties. It has now been found that the aminoheterocyclylamides of formula I have excellent pesticidal properties, especially against endoparasites.
The alkyl groups present in the definitions of the substituents may be straight-chained or branched and are for example methyl, ethyl, n-propyl, isopropyl, n-butyl, sec.-butyl, isobutyl, tert.-butyl, pentyl and hexyl, as well as the branched isomers thereof.
As a rule, halogen signifies fluorine, chlorine, bromine or iodine. The same applies to halogen in combination with other significances, such as halogenalkyl or halogenphenyl.
Halogenalkyl groups preferably have a chain length of 1 to 6 carbon atoms. Halogenalkyl 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 1 to 6 carbon atoms. Alkoxy is for example methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec.-butoxy and tert.-butoxy, as well as the isomers pentyloxy and hexyloxy; preferably methoxy and ethoxy.
Preference is given to compounds of formula I, wherein
R
1
is halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkyl or unsubstituted or mono- to penta-substituted phenyl, whereby the substituents are selected from the group comprising C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, aryloxy, halogen, cyano and nitro, whereby if the number of substituents is greater than 1, the substituents may be the same or different;
R
2
is hydrogen, C
1
-C
6
-alkyl, (C
1
-C
6
-alkylene)phenyl or pyridyl;
X
1
is N or C(CN);
X
2
is N or C(CN);
X
3
is O or S;
Q is CH or N;
R
3
and R
4
, independently of one another, are hydrogen, C
1
-C
6
-Alkyl or together with the C-atom to which they are bonded, a C
3
-C
7
-cycloalkyl ring;
R
5
is a substituent from the group comprising C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, aryloxy, halogen, cyano, hydroxy, amino and nitro, whereby if m is greater than 1, the substituents may be identical or different;
m is 1, 2 or 3; and
n is 0 or 1;
The especially preferred compounds in the context of formula I include substances of formula Ia
wherein the substituents are defined as under formula I.
Preferred embodiments in the context of the compounds of formulae I and Ia are:
(1) A compound of formula I, wherein X
3
is O;
(2) A compound of formula I, wherein R
1
is halogen or C
1
-C
6
-haloalkyl; preferably fluorine, chlorine or C
1
-C
4
-haloalkyl; more preferably chlorine or C
1
-C
2
-haloalkyl; most preferably chlorine or trifluoromethyl;
(3) A compound of formula I, wherein R
2
is hydrogen or C
1
-C
6
-alkyl; preferably hydrogen or C
1
-C
2
-alkyl; most preferably hydrogen;
(4) A compound of formula I, wherein R
3
and R
4
, independently of one another, are hydrogen, C
1
-C
2
-alkyl, or together with the C-atom to which they are bonded, a C
3
-C
6
-cyclo-alkyl ring; preferably hydrogen or together with the C-atom to which they are bonded, a C
3
-C
5
-cycloalkyl ring; most preferably hydrogen or together with the C-atom to which they are bonded, a cyclopropyl ring;
(5) A compound of formula I, wherein m is 1 or 2, preferably 2;
(6) A compound of formula I, wherein n is 0;
(7) A compound of formula I, wherein R
2
is halogen or C
1
-C
6
-haloalkyl; R
2
is hydrogen or C
1-C
6
-alkyl; R
3
and R
4
, independently of one another, are hydrogen, C
1
-C
2
-alkyl or together with the C-atom to which they are bonded, is a C
3
-C
6
-cycloalkyl ring; m is 1 or 2; and n is 0;
(8) A compound of formula I, wherein R
1
is fluorine, chlorine or C
1
-C
4
-haloalkyl; R
2
is hydrogen or C
1
-C
2
-alkyl; R
3
and R
4
are hydrogen or together with the C-atom to which they are bonded, a C
3
-C
5
-cycloalkyl ring; m is 2; and n is O;
(9) A compound of formula I, wherein R
1
is chlorine or C
1
-C
2
-haloalkyl; R
2
is hydrogen; R
3
and R
4
are hydrogen or together with the C-atom to which they are bonded, a cyclopropyl ring; m is 2; and n is O.
A further object of the invention is the process for the preparation of the compounds of formula I and optionally the enantiomers thereof, for example characterised in that a compound of formula
which is known or may be produced analogously to corresponding known compounds, and wherein R
1
, R
2
, X
1
and X
2
are defined as given for formula I, is reacted with a compound of formula
which is known or may be produced analogously to corresponding known compounds, in which X
3
, R
3
, R
4
, R
5
, m, n und Q are defined as for formula I, and Z is a leaving group, optionally in the presence of a basic catalyst, and if desired, a compound of formula I which is obtainable by this process or in another way, or an enantiomer thereof, may be converted into another compound of formula I or an enantiomer thereof, a mixture of enantiomers which is obtainable by this process is separated and the desired enantiomer isolated.
Suitable leaving groups are halogen, C
1
-C
6
-alkoxy or hydroxy, preferably chlorine.
Suitable bases for facilitating the reaction are e.g. trialkylamines, basic heterocycles or phosphines. Triethylamine, diisopropylethylamine, pyridine, 4-(N,N-dimethylamino)pyridine, quinuclidine, 1,5-diazabicyclo[5.4.0]undec-5-ene (DBU) and triphenylphosphine may be mentioned by way of example. Diisopropylethylamine is preferred.
The reagents may be reacted together as such, i.e. without adding a solvent or diluent, for example in the melt. However, for the most part, it is advantageous to add an inert solvent or diluent or a mixture thereof. Examples of such solvents or diluents that may be mentioned are: aromatic, aliphatic and alicyclic hydrocarbons and halogen-hydrocarbons, such as benzene, toluene, xylene, mesitylene,

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