Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Reexamination Certificate
2002-07-26
2004-10-19
O'Sullivan, Peter (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
C504S343000, C514S610000, C564S103000, C564S104000, C564S108000
Reexamination Certificate
active
06806292
ABSTRACT:
The present application relates to novel substituted imide derivatives, to a process for their preparation and to their use for controlling animal pests and as herbicides.
Certain imide derivatives are already known (cf. WO 91/04 965, WO 93/04 032, EP-A-403 159; J. Organomet. Chem. (1975), 97 (1), pp. 39-44; Bul. Soc. Chim. Belg. (1981), 90 (1), pp. 89-98). Insecticidal and/or herbicidal properties of some of these compounds have also been disclosed.
This invention, accordingly, provides novel substituted imide derivatives of the general formula (I)
in which
R
1
represents optionally substituted cycloalkyl,
R
2
represents optionally substituted alkyl or optionally substituted cycloalkyl,
R
3
represents alkyl, alkoxy, alkylthio, amino, alkylamino or dialkylamino and
R
4
represents cyano or nitro.
If appropriate, the imide derivatives of the formula (I) can also 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 substituted imide derivatives of the formula (I) are obtained when amines of the formula (II)
in which
R
1
and R
2
are as defined above are reacted with ethaneimidate of the formula (III)
in which
R
3
and R
4
are as defined above,
R
5
represents alkyl and X represents oxygen or sulphur in the presence of a diluent.
The novel imideamide derivatives of the general formula (I) have highly pronounced biological properties and are particularly suitable 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; for controlling animal pests, such as parasitic nematodes, in veterinary medicine; and also for use as herbicides.
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 above and below are illustrated below.
R
1
preferably represents C
3
-C
6
-cycloalkyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-alkylthio.
R
2
preferably represents C
1
-C
4
-alkyl which is optionally substituted by halogen, cyano or C
1
-C
4
-alkoxy or represents C
3
-C
6
-cycloalkyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-alkylthio.
R
3
preferably represents C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, amino, C
1
-C
4
-alkylamino or di-(C
1
-C
4
)-alkylamino.
R
1
particularly preferably represents cyclopentyl or cyclohexyl, each of which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, methylthio and ethylthio.
R
2
particularly preferably represents methyl, ethyl or n- or i-propyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy; or represents cyclopentyl or cyclohexyl, each of which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, methylthio and ethylthio.
R
3
particularly preferably represents methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; methoxy, ethoxy, n- or i-propoxy; methylthio, ethylthio, n- or i-propylthio; amino; methylamino, ethylamino, n- or i-propylamino; ethylmethyl-amino, dimethylamino, diethyl amino, methyl-n-propyl -amino, methyl-i-propylamino, ethyl-n-propyl-amino, ethyl-i-propyl-amino, i-propyl-n-propyl-amino or diisopropylamino.
R
1
very particularly preferably represents cyclopentyl or cyclohexyl, each of which is optionally mono- or disubstituted by identical or different substituents from the group consisting of chlorine, methyl and methoxy.
R
2
very particularly preferably represents methyl, ethyl or isopropyl.
R
3
very particularly preferably represents methyl, ethyl, isopropyl; methoxy, ethoxy, isopropoxy; methylthio, ethylthio, isopropylthio; amino; methylamino, ethylamino; dimethylamino, ethylmethylamino or diethylamino.
In the definitions, the hydrocarbon chains, such as, for example, alkyl, are in each case straight-chain or branched.
Preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being preferred.
Particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.
Very particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred.
Using, for example, R-(−)-cyclohexylamine and methylthio N-cyano-ethaneimidate as starting materials, the course of the reaction of the process according to the invention can be represented by the following equation:
The amines of the formula (II) required as starting materials for carrying out the process according to the invention are generally known compounds of organic chemistry and/or obtainable in a generally known manner. The cyclohexylamine derivatives of the formula (II) can be obtained particularly advantageously by hydrogenation of the corresponding phenylamine derivatives.
The formula (III) provides a general definition of the ethaneimidates further to be used as starting materials in the process according to the invention. In this formula, R
5
preferably represents C
1
-C
4
-alkyl, such as, in particular, methyl or ethyl.
Most of the N-cyano-ethaneimidates are known (cf., for example, J. Org. Chem. 28, 1816 (1963); Chem. Berichte 100, 2604 (1967); Tetrahedron Letters 1968, 5523; Synthesis 1975, 332; J. Org. Chem. 35, 2067 (1970); U.S. Pat. No. 3,910,928) and/or they can be obtained by customary processes.
Some of the N-nitro-ethaneimidates are also known (cf., for example, J. Org. Chem. USSR (English) 9 (1973), 1233-1236; JACS 76 (1954), 1877; Rec. Trav. Chim. Pay-Bas 81, 69 (1962); JP-A-0156947), and/or they can be obtained by customary processes, such as, in particular, by customary nitration of the corresponding NO
2
-free ethaneimidates of the formula (III).
The process according to the invention is preferably carried out in the presence of a diluent. Preference is given to using alcohols, such as methanol and ethanol; nitrites, such as acetonitrile, or esters, such as ethyl acetate. It is also possible to carry out the process in water or organic/aqueous mixtures.
When carrying out the process according to the invention, preference is given to using equimolar amounts; however, it is also possible to employ an excess of one or the other starting material.
When carrying out the process according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the process is carried out at temperatures between 0° C. and 100° C., preferably between 20° C. and 80° C.
Work-up and isolation of the end products are carried out in a generally known manner.
The active compounds are suitable for controlling animal pests, in particular insects, arachnids and nematodes, which are encountered in agriculture, in forests, in the protection of stored products and of materials, and in the hygiene sector, and have good plant tolerance and favourable toxicity to warm-blooded animals. The active compounds are particularly suitable for controlling nematodes. They may be preferably employed as crop protection agents. They are active against normally sensitive and resistant species and against all or some stages of development. The abovementioned pests include:
From the order of the Isopoda, for example,
Oniscus asellus, Armadillidium vulgare
and
Porcellho scaber.
From the order of the Diplopoda, for example,
Blaniulus guttulatus.
From the order of t
Andersch Wolfram
Drewes Mark Wilhelm
Feucht Dieter
Gesing Ernst-Rudolf
Harder Achim
Bayer Aktiengesellschaft
Harmuth Raymond J.
Henderson Richard E. L.
O'Sullivan Peter
LandOfFree
Substituted imide derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Substituted imide derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted imide derivatives will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3276320