Imidamide derivatives

Details Imidamide derivatives Imidamide derivatives

2001-02-05

2003-10-28

Raymond, Richard L. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Nitrogen containing other than solely as a nitrogen in an...

C514S610000, C564S103000, C564S105000, C564S106000, C564S108000

Reexamination Certificate

active

06638979

ABSTRACT:

This application is a 371 of PCT/EP99/04747, filed Jul. 7, 1999.
The present invention relates to novel imidamide derivatives, to a process for their preparation and to their use for controlling animal pests.
Certain imidamide derivatives are already known (cf. WO 91 04 965, WO 93 04 032, EP 0 403 159; J. Organomet. Chem. (1975), 97 (1), pp. 39-44; Bull. Soc. Chim. Belg. (1981), 90 (1), pp. 89-98). The insecticidal properties of some of these compounds have also been known.
This invention provides novel imidamide derivatives of the general formula (I)
in which
R represents cyano or nitro,
R
1
represents hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted phenyl,
R
2
represents hydrogen, optionally substituted alkyl or optionally substituted cycloalkyl and
R
3
represents the groupings
 where
R
4
and R
5
independently of one another each represent hydrogen, optionally substituted alkyl or optionally substituted cycloalkyl,
R
6
and R
7
independently of one another represent optionally substituted aryl, optionally substituted cycloalkyl or represent an optionally substituted mono- or bicyclic, nitrogen-free heterocycle.
R
8
represents alkyl or optionally substituted aryl,
X represents a single bond, represents in each case straight-chain or branched alkanediyl, alkenediyl, alkinediyl and also represents the groupings —A—O—, —A—S—, —A—O—A′-, —A—S—A′—, —A—N(Alk)- or —A—N(Alk)-A′—, where the moiety A is attached to the C atom of the grouping —C(R
4
R
5
)—X—R
6
;
Alk represents alkyl and
A and A′ independently of one another each represent straight-chain or branched alkanediyl and
Y represents a single bond and also the groupings —O—A—, —O—A″—O—, —O—A″—S—, —O—A″—SO—, —O—A″—SO
2
—, —O—A″—O—A′— or —O—A″—S—A′—, where the O atom of these groupings is always attached to the N atom of the skeleton of the formula (I):
A and A′ are each as defined above and
A″ represents straight-chain or branched alkanediyl having it least 2 carbon atoms between the heteroatoms.
with the proviso that for R=CN and R
2
=H the compounds in which
are excluded.
Depending, inter alia, on the substituents, the imidamide derivatives of the formula (I) may be present as optical and/or geometrical isomers. The present invention relates both to the various isomer mixtures and to the pure isomers.
The novel imidamide derivatives of the general formula (I) are obtained when ethaneimido esters of the formula (II)
in which
R and R
1
are each as defined above,
Q represents oxygen or sulphur and
Z represents alkyl
are reacted with amines of the formula (III)
in which
R
2
and R
3
are each as defined above
in the presence of a diluent.
The novel imidamide derivatives of the general formula (I) have pronounced biological properties and are suitable in particular for controlling animal pests, such as insects, arachnids and, in particular, nematodes encountered in agriculture, in forests, in the protection of stored products and materials and in the hygiene sector.
The formula (I) provides a general definition of the compounds according to the invention. Preferred substituents or ranges of the radicals listed in the formulae mentioned above and below are illustrated below.
R preferably represents cyano or nitro.
R
1
preferably represents hydrogen, represents optionally halogen-, cyano- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkyl, represents C
3
-C
6
-cycloalkyl which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen C
1
-C
4
-alkyl or represents phenol which is optionally mono- to trisubstitued by identical or different substituents, possible substituents being the phenyl substituents mentioned under R
6
.
R
2
preferably represents hydrogen, represents optionally halogen-, cyano- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkyl or represents C
3
-C
6
-cycloalkyl which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen or C
1
-C
4
-alkyl;
R
3
preferably represents the groupings
 where
R
4
and R
5
independently of one another each preferably represent hydrogen, represent optionally halogen-, cyano- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkyl or represent C
3
-C
6
-cycloalkyl which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen or C
1
-C
4
-alkyl.
R
6
and R
7
independently of one another each preferably represent phenyl, naphthyl, dihydronaphthyl and tetrahydronaphthyl, each of which is optionally mono- to pentasubstituted by identical or different substituents, possible substituents being those below:
hydroxyl, amino, cyano, nitro, halogen; in each case optionally hydroxyl-, cyano- or halogen-substituted C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylamino and di-(C
1
-C
4
-alkyl)amino; in each case optionally halogen-substituted C
1
-C
4
-alkyl-carbonyl, C
1
-C
4
-alkoxy-carbonyl, C
1
-C
4
-alkyl-carbonyl-amino, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulphinyl and C
1
-C
4
-alkylsulphonyl, aminocarbonyl, aminothiocarbonyl, C
1
-C
4
-alkylaminocarbonyl, di-(C
1
-C
4
-alkyl)amino-carbonyl, amino-sulphonyl, C
1
-C
4
-alkylaminosulphonyl and di-(C
1
-C
4
-alkyl)amino-sulphonyl; and also phenyl, phenoxy, phenylthio, phenylsulphinyl, phenylsulphonyl, benzyl and phenylamino, each of which is optionally substituted by hydroxyl, cyano, nitro, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulphinyl, C
1
-C
4
-alkylsulphonyl and C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy, C
1
-C
4
-halogenalkylthio, C
1
-C
4
-halogenalkylsulphinyl and C
1
-C
4
-halogenoalkylsulphonyl having in each case 1 to 5 identical or different halogen atoms from the series consisting of chlorine, fluorine and bromine;
furthermore represent C
3
-C
12
-cycloalkyl or C
5
-C
12
-cycloalkenyl, each of which is optionally mono- to pentasubstituted by identical or different substituents, possible substituents being:
Halogen, optionally substituted C
1
-C
4
-alkyl, preferred substituents being: halogen, such as fluorine, chlorine, bromine, optionally substituted C
2
-C
6
-cycloalkyl and optionally substituted phenyl;
furthermore C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy and also C
1
-C
4
-halogenoalkyl and C
1
-C
4
-halogenoalkoxy having in each case 1to 5 identical or different halogen atoms selected from the series consisting of fluorine, chlorine and bromine;
and also represent a saturated or partially unsaturated or unsaturated mono-, bi- or tricyclic nitrogen-free heterocycle having 4 to 10 C atoms and 1to 3 identical or different heteroatoms, such as O and S atoms, which is optionally mono- to pentasubstituted by identical or different substituents, possible substituents being the phenyl substituents mentioned under R
6
.
R
8
preferably represents C
1
-C
4
-alkyl or represents phenyl and naphthyl, each of which is optionally mono- to pentasubstituted by identical or different substituents, possible substituents being the phenyl substituents mentioned under R
6
.
X preferably represents a single bond, represents in each case straight-chain or branched C
1
-C
6
-alkanediyl, C
2
-C
6
-alkenediyl or C
2
-C
6
-alkinediyl and also represents the groupings —A—O—, —A—S—, —A—O—A′—, —A—S—A′—, —A—N(Alk)- or —A—N(Alk)-A′—,
where
Alk preferably represents C
1
-C
4
-alkyl and
A and A′ independently of one another each preferably represent straight-chain or branched C
1
-C
6
-alkanediyl.
Y preferably represents a single bond and also the groupings —O—A—, —O—A″—O—, —O—A″—S—, —O—A″—SO—, —O—A″—SO
2
—, —O—A″—O—A′— or —O—A″—S—A′—, where
A and A′ are each preferably as defined above.
A″ preferably represents straight-chain or branched C
2
-C
4
-alkanediyl having at least 2 carbon atoms between the heteroatoms.
The preferred definitions are given with the proviso that for R&e

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