Pesticidal n-heteroaryl alpha-alkoximino-carboxamides

Details Pesticidal n-heteroaryl alpha-alkoximino-carboxamides Pesticidal n-heteroaryl alpha-alkoximino-carboxamides

2002-05-28

2003-09-16

McKane, Joseph K. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C514S361000, C548S128000, C548S197000, C548S214000, C549S068000

Reexamination Certificate

active

06620767

ABSTRACT:

This application is a 371 of PCT/EP00/11840 filed on Nov. 27, 2000.
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
;
R
3
is C
1
-C
6
-alkyl;
R
4
is unsubstituted or substituted phenyl, unsubstituted or substituted benzyl or unsubstituted or substituted heterocyclyl, whereby each of the substituents, independently of each other, is selected 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 the number of substituents is greater than 1, the substituents 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;
Q is C
1
-C
6
-alkylene;
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
and X
4
, independently of each other, are O or S; 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.
Corresponding alkylene groups may likewise be straight-chained or branched and are for example methylene, ethylene, n-propylene, isopropylene, n-butylene, sec.-butylene, isobutylene, tert.-butylene, pentylene and hexylene, 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.
Heterocyclyl signifies an aliphatic or aromatic, optionally benzocondensed, threefold to eightfold, cyclic group which contains at least one hetero atom from the group comprising oxygen, nitrogen and sulphur, with five- and sixfold heterocycles being preferred. Typical representatives are, for example, dioxolanyl, pyrrolidinyl, piperidinyl, morpholinyl, pyridyl, pyrryl, furyl, thienyl, imidazolyl, tetrahydrofuryl, tetrahydropyrryl, tetrahydropyranyl, dihydrofuryl, dihydropyranyl, benzofuryl, benzothienyl, isoxazolyl, oxazolyl, thiazolyl, oxazolinyl, oxazolidinyl, indolyl, imidazolinyl, imidazolidinyl and dioxanyl.
Preferred compounds within the context of formula I are those in which
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;
R
3
is C
1
-C
6
-alkyl;
R
4
is unsubstituted or substituted phenyl, unsubstituted or substituted benzyl or unsubstituted or substituted heterocyclyl, whereby each of the substituents, independently of each other, is selected 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 the number of substituents is greater than 1, the substituents may be identical or different.
Q is C
1
-C
6
-alkylene;
X
1
is N or C(CN);
X
2
is N or C(CN);
X
3
and X
4
, independently of each other, are O or S; and
n is 0 or 1.
Especially preferred embodiments in the context of the compounds of formula I are:
(1) 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;
(2) 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;
(3) A compound of formula I, wherein R
3
is C
1
-C
4
-alkyl; preferably C
1
-C
2
-alkyl; most preferably methyl;
(4) A compound of formula I, wherein R
4
is unsubstituted or substituted heterocyclyl, whereby the substituents are selected from the group comprising C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, aryloxy, halogen, cyano, hydroxy, amino and nitro, whereby if the number of substituents is greater than 1, the substituents may be identical or different; preferably unsubstituted or substituted heterocyclyl, whereby the substituents are selected from the group comprising halogen, cyano and nitro, whereby if the number of substituents is greater than 1, the substituents may be identical or different; more preferably unsubstituted or substituted heterocyclyl, whereby the substituents are selected from the group comprising fluorine, chlorine or bromine, whereby if the number of substituents is greater than 1, the substituents may be identical or different; most preferably unsubstituted or chlorine-substituted heterocycly; especially pyrrolidinyl, piperidinyl, pyridyl, pyrryl, furyl, thienyl, tetrahydrofuryl, benzofuryl or benzothienyl;
(5) A compound of formula I, wherein Q is C
1
-C
2
-alkylene;
(6) A compound of formula I, wherein X
3
is O;
(7) A compound of formula I, wherein X
4
is O;
(8) A compound of formula I, wherein n is 1;
(9) A compound of formula I, wherein R
1
is halogen or C
1
-C
6
-haloalkyl; R
2
is hydrogen or C
1
-C
6
-alkyl; R
3
is C
1
-C
4
-alkyl; R
4
is unsubstituted or substituted heterocyclyl, whereby the substituents are selected from the group comprising C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, aryloxy, halogen, cyano, hydroxy, amino and nitro, whereby if the number of substituents is greater than 1, the substituents may be identical or different; Q is C
1
-C
2
-alkylene; X
3
and X
4
are O; and n is 1;
(10) 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
is C
1
-C
2
-alkyl; R
4
is unsubstituted or substituted heterocyclyl, whereby the substituents are selected from the group comprising halogen, cyano and nitro, whereby if the number of substituents is greater than 1, the substituents may be identical or different; Q is C
1
-C
2
-alkylene; X
3
and X
4
are O; and n is 1;
(11) A compound of formula I, wherein R
1
is chlorine or C
1
-C
2
-haloalkyl; R
2

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