Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-02-09
2002-03-05
Shah, Mukund J. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S345000, C514S183000, C546S243000, C546S246000
Reexamination Certificate
active
06353001
ABSTRACT:
The invention relates to compounds of formula:
wherein
A is an unsubstituted or substituted aromatic or non-aromatic, monocyclic or bicyclic heterocyclic radical wherein a ring nitrogen atom may have been replaced by a group
R
1
is hydrogen or C
1
-C
3
alkyl;
R
2
is hydrogen or C
1
-C
3
alkyl;
R
3
is hydrogen, an unsubstituted or substituted C
1
-C
6
alkyl, C
3
-C
6
cycloalkyl, C
2
-C
6
alkenyl or C
2
-C
6
alkynyl group, or C(═O)—R
5
,
R
5
is C
1
-C
4
alkyl, C
1
-C
4
alkoxy, an unsubstituted or substituted phenyl, phenoxy or benzyloxy group, or N(R
6
)
2
,
each R
6
, independently of the other, is hydrogen, C
1
-C
4
alkyl or unsubstituted or substituted phenyl,
X is CH—NO
2
, N—CN or N—NO
2
and
n is from 1 to 3,
in free form or in salt form, where appropriate to tautomers of those compounds and to the salts thereof, to processes for the preparation of those compounds and tautomers and to the use thereof, to pesticidal compositions comprising an active ingredient selected from those compounds and tautomers, to a process for the preparation of those compositions and to the use thereof, to plant propagation material treated with those compositions, to a method of controlling pests, to intermediates and, where appropriate, the tautomers thereof, in each case in free form or in salt form, to processes for the preparation of those active ingredients and to processes for the preparation of those intermediates and the tautomers thereof.
The invention relates especially to compounds c: formula I wherein
A is an unsubstituted or mono- to tetra-substituted aromatic or non-aromatic, mono-cyclic or bicyclic heterocyclic radical wherein a ring nitrogen atom may have been replaced by a group
and wherein one or two of the substituents of A may be selected from the group consisting of C
1
-C
3
alkyl, halo-C
1
-C
3
alkyl, cyclopropyl, halocyclopropyl, C
2
-C
3
alkenyl, C
2
-C
3
alkynyl, halo-C
2
-C
3
alkenyl, halo-C
2
-C
3
alkynyl, hydroxy, mercapto, halo-C
1
-C
3
alkoxy, C
1
-C
3
allylthio, halo-C
1
-C
3
alkylthio, allyloxy, propargyloxy, allylthio, propargylthio, haloallyloxy, haloallylthio, cyano and nitro, and from one to four of the substituents of A may be selected from the group consisting of C
1
-C
3
alkyl, C
1
-C
3
alkoxy and halogen;
R
1
is hydrogen or C
1
-C
3
alkyl;
R
2
is hydrogen or C
1
-C
3
alkyl;
R
3
is hydrogen, C
1
-C
6
alkyl, halo-C
1
-C
6
alkyl, C
1
-C
6
alkoxy-C
1
-C
6
alkyl, C
1
-C
6
alkylthio-C
1
-C
6
alkyl, phenoxy-C
1
-C
6
alkyl, phenylthio-C
1
-C
6
alkyl, C
3
-C
6
cycloalkyl-C
1
-C
6
alkyl, benzyloxy-C
1
-C
6
alkyl, di(C
1
-C
4
alkyl)amino-C
1
-C
6
alkyl, cyano-C
1
-C
6
alkyl, C
1
-C
4
alkylcarbonyl-C
1
-C
6
alkyl, C
1
-C
4
alkoxycarbonyl-C
1
-C
6
alkyl, C
3
-C
6
cycloalkyl, halo-C
3
-C
6
cycloalkyl, C
2
-C
6
alkenyl, halo-C
2
-C
6
alkenyl, C
2
-C
6
alkynyl, halo-C
2
-C
6
alkynyl or C(═O)—R
5
,
R
5
is C
1
-C
4
alkyl, C
1
-C
4
alkoxy, phenyl, phenoxy or benzyloxy, or phenyl, phenoxy or benzyloxy substituted by from one to three substituents selected from the group consisting of halogen, C
1
-C
4
alkyl, halo-C
1
-C
4
alkyl, C
1
-C
4
alkoxy, nitro and cyano, or is N(R
6
)
2
,
each R
6
, independently of the other, is hydrogen, C
1
-C
4
alkyl or phenyl, or phenyl substituted by from one to three substituents selected from the group consisting of halogen, C
1
-C
4
alkyl, halo-C
1
-C
4
alkyl, C
1
-C
4
alkoxy, nitro and cyano,
X is CH—NO
2
, N—CN or N—NO
2
and
n is from 1 to 3,
and the tautomers thereof, in each case in free form or in salt form.
Certain 3-substituted 2-nitromethylidene-piperidines and 2-nitromethylidene-pyrrolidines are proposed in the literature as arthropodicidal active ingredients in pesticides. The biological properties of those known compounds are not, however, fully satisfactory in the area of pest control and there is therefore a need to provide further compounds having pest-control properties, especially for controlling insects. That problem is solved according to the invention by the provision of the present compounds of formula I.
Some of the compounds of formula I can be in the form of tautomers. That relates, for example, to the heterocyclic radicals A that are substituted by a hydroxy group or by a mercapto group wherein, depending on the structure, the hydroxy or the oxo form, or the mercapto or the thioxo form, respectively, may be present, or the two tautomeric forms may be present alongside one another.
Compounds of formula I having at least one basic centre are capable of forming acid addition salts. Those salts are formed, for example, with strong inorganic acids, such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids, such as unsubstituted or substituted, for example halo-substituted, C
1
-C
4
alkanecarboxylic acids, for example acetic acid, or saturated or unsaturated dicarboxylic acids, for example oxalic, malonic, succinic, maleic, fumaric or phthalic acid, or hydroxycarboxylic acids, for example ascorbic, lactic, malic, tartaric or citric acid, or benzoic acid, or with organic sulfonic acids, such as unsubstituted or substituted, for example halo-substituted, C
1
-C
4
alkanesulfonic or arylsulfonic acids, for example methanesulfonic or p-toluenesulfonic acid. Furthermore, compounds of formula I having at least one acidic group are capable of forming salts with bases. Suitable salts with bases are, for example, metal salts, such as alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower alkylamine, for example ethylamine, diethylamine, triethylamine or dimethylpropylamine, or a mono-, di- or tri-hydroxy-lower alkylamine, for example mono-, di- or tri-ethanolamine. Where appropriate, corresponding internal salts may be formed. Preference is given within the scope of the invention to agrochemically acceptable salts, but salts that have disadvantages for agrochemical purposes are also included; they are used, for example, in the isolation or purification of free compounds of formula I or the agrochemically acceptable salts thereof. Hereinbefore and hereinafter, the expression “compound(s) of formula I” thus always also includes the salts of those compounds, their tautomers and the salts of the tautomers.
Suitable as heteroatoms in the basic ring structure of the heterocyclic radical A are any elements of the Periodic Table that are capable of forming at least two covalent bonds, but preference is given to oxygen, nitrogen and sulfur, especially nitrogen and sulfur, more especially nitrogen.
Halogen—per se and as a structural element of other groups and compounds, such as haloalkyl, haloalkylthio, haloalkoxy, halocyclopropyl, haloalkenyl, haloalkynyl, haloallyloxy and haloallylthio—is fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine, more especially fluorine or chlorine and most especially chlorine.
Unless otherwise defined, carbon-containing groups and compounds each contain from 1 up to and including 6, preferably from 1 up to and including 3, more especially 1 or 2, carbon atoms.
Cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, preferably cyclopropyl.
Alkyl—as a group per se and as a structural element of other groups and compounds, such as haloalkyl, alkoxy, haloalkoxy, alkylthio and haloalkylthio—in each case taking due account of the number of carbon atoms in the group or compound in question—is either straight-chained, i.e. methyl, ethyl, propyl, butyl, pentyl or hexyl, or branched, e.g. isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl or isohexyl.
Alkenyl, haloalkenyl, alkynyl and haloalkynyl are straight-chained or branched and each contain two or preferably one unsaturated carbon-carbon bond(s). The double or triple bonds of those substituents are separated from the remainder of the compound of formula I preferably by at least one saturated carbon atom. The following may be mentio
Gonda Jozef
Gsell Laurenz
Jacob Olivier
Maienfisch Peter
Patel Sudhaker B.
Shah Mukund J.
Syngenta Investment Corporation
Teoli, Jr. William A.
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