5,5-Disubstituted thiazolidine derivative pesticides

Details 5,5-Disubstituted thiazolidine derivative pesticides 5,5-Disubstituted thiazolidine derivative pesticides

2002-09-11

2004-03-30

McKane, Joseph K. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

06713629

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to novel 5,5-disubstituted thiazolidine derivatives, which have pesticidal activity. In particular, the novel 5,5-disubstituted thiazolidine derivatives of the present invention have fungicidal activity. The preparation and use, in agriculture and horticulture, of agrochemical compositions containing these novel fungicidal 5,5-disubstituted thiazolidine derivatives is also disclosed. In addition, novel methods of preparing the 5,5-disubstituted thiazolidine derivatives of the present invention are disclosed.
2. Description of the Related Art
It is known in the art that certain thiazolidine derivatives such as those disclosed in GB-013723 have insecticidal properties. Further, it is known in the art that compounds which do not have any substituents at the 5-position of the thiazolidine ring or those that are monosubstituted or lower dialkyl substituted can be prepared using substituted hydrazines derived from a dithiocarbazate salt, R
3
NHNHC(═S)S
−
M
+
, as a starting material according to Brown et al. “Structure and Antimicrobial Activity of the 3-Aminorhodanines.”
J. Org Chem. Vol.
24. (1959), pp. 1056-1060,
J. Org Chem. Vol.
26. (1961), p. 5103, JP-A-1986-200978, and Talukdar, P. B. “Studies on Dithiocarbamates, Part I. Some Derivatives of Rhodamime.”
Indian J. Appl. Chem. Vol.
28. (1965), pp. 197-202. In the case of 5,5-disubstituted thiazolidine derivatives, however, when their substituent is an aryl group, cyclization to a thiazolidine ring is very difficult to achieve by known methods and side reactions occur during the cyclization reaction.
In view of the prior art at the time the present invention was made, it was not obvious to those of ordinary skill in the pertinent art how the desired 5,5-disubstituted thiazolidine derivatives having fungicidal activity could be provided.
SUMMARY OF THE INVENTION
In accordance with the present invention, 5,5-disubstituted thiazolidine derivatives are provided having the formula:
wherein
R
1
is selected from the group consisting of C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
cycloalkyl, and optionally substituted phenyl;
R
2
is selected from the group consisting of C
2
-C
6
alkyl and phenyl substituted by A
n
;
A is each independently selected from the group consisting of H, halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
alkenyloxy, C
1
-C
6
alkynyloxy, nitro, optionally substituted amino, C
1
-C
6
alkylthio, C
1
-C
6
alkoxycarbonyl, phenoxy, phenyl, optionally substituted pyridyl, optionally substituted thienyl, and optionally substituted furyl;
n is 0-5;
X is selected from the group consisting of O, NH, N—OH, optionally substituted arylimino, optionally substituted alkylimino, optionally substituted carbamoyloxyimino, optionally substituted acyloxyimino, and optionally substituted aroyloxyimino;
Y is selected from the group consisting of O, S, N—OH, optionally substituted arylimino, optionally substituted alkylimino, optionally substituted carbamoyloxyimino, optionally substituted sulfamoyloxyimino, optionally substituted aroyloxyimino, optionally substituted alkoxycarbonyloxyimino, optionally substituted alkylhydrazono, optionally substituted phenylhydrazono, and alkylsulfenyl; and
Z is optionally substituted phenylamino.
The present invention also relates to the preparation of these compounds. Further, the present invention is directed to agrochemical compositions comprising as an active ingredient at least one of the novel 5,5-disubstituted thiazolidine derivatives of the present invention, as well as to the use of these active ingredients or compositions for pest control, and, in particular as fungicides useful in agriculture and horticulture.
For a better understanding of the present invention, reference is made to the following description and its scope will be pointed out in the appended claims.
DETAILED DESCRIPTION OF THE INVENTION
For purposes of the present invention the general terms used hereinabove and hereinbelow have the following meanings, unless otherwise defined:
Alkyl groups are, in accordance with the number of carbon atoms, straight-chain or branched and will typically be selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-amyl, tert-amyl, 1-hexyl, and 3-hexyl;
Cycloalkyl groups are generally selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
Halogen and halo substituents are selected from the group consisting of fluoro, chloro, bromo, and iodo, with fluoro, chloro, and bromo being the preferred substituents;
Haloalkyl may contain identical or different halogen atoms, typically selected from the group consisting of fluoromethyl, difluoromethyl, difluorochloromethyl, trifluoromethyl, chloromethyl, and trichloromethyl;
Alkoxy is typically selected from the group consisting of methoxy, ethoxy, propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy, and tert-butyloxy, while methoxy and ethoxy are preferred alkoxy substituents;
Aryl is typically selected from the group consisting of substituted phenyl, substituted naphthyl, furoyl, thienyl, a six-membered heteroaromatic ring system such as pyridyl and pyrimidyl, a five-membered heteroaromatic ring such as thiazoryl, oxazoryl, pyrazoryl, thiadiazoryl and oxadiazoryl; and
Aroyl is typically selected from the group consisting of substituted benzoyl, furancarbonyl, thiophenecarbonyl, and a six-membered heteroaromatic carboxylic acid residue such as nicotinyl and pyridyl.
The present invention is directed to 5,5-disubstituted thiazolidine derivatives having the following formula:
wherein
R
1
is selected from the group consisting of C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
cycloalkyl, and optionally substituted phenyl;
R
2
is selected from the group consisting of C
2
-C
6
alkyl and phenyl substituted by A
n
;
A is each independently selected from the group consisting of H, halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
alkenyloxy, C
1
-C
6
alkynyloxy, nitro, optionally substituted amino, C
1
-C
6
alkylthio, C
1
-C
6
alkoxycarbonyl, phenoxy, phenyl, optionally substituted pyridyl, optionally substituted thienyl, and optionally substituted furyl;
n is 0-5;
X is selected from the group consisting of O, NH, N—OH, optionally substituted arylimimo, optionally substituted alkylimino, optionally substituted carbamoyloxyimino, optionally substituted acyloxyimino, and optionally substituted aroyloxyimino;
Y is selected from the group consisting of O, S, N—OH, optionally substituted arylimino, optionally substituted alkylimino, optionally substituted carbamoyloxyimino, optionally substituted sulfamoyloxyimino, optionally substituted aroyloxyimino, optionally substituted alkoxycarbonyloxyimino, optionally substituted alkylhydrazono, optionally substituted phenylhydrazono, and alkylsulfenyl; and
Z is optionally substituted phenylamino.
The compounds of Formula 1, which are 5,5-disubstituted thiazolidine derivatives, one of substituents of which is an aryl, may be prepared as shown in Scheme 1 and Scheme 2 below.
wherein,
R
1
is selected from the group consisting of C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
cycloalkyl, and optionally substituted phenyl;
R
2
is selected from the group consisting of C
2
-C
6
alkyl and phenyl substituted by A
n
;
A is each independently selected from the group consisting of H, halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
alkenyloxy, C
1
-C
6
alkynyloxy, nitro, optionally substituted amino, C
1
-C
6
alkylthio, C
1
-C
6
alkoxycarbonyl, phenoxy, phenyl, optionally substituted pyridyl, optionally substituted thienyl, and optionally substituted furyl;
M
+
is an ion form of a metal or tertiary amine;
n is 0-5; and
R
3
is optionally substituted phenyl.
As shown in Scheme 1 the chloronitriles 4, which are prepared directly by the reaction of alkyl aryl ketones with trimethylsilyl cyanide in the presence of titanium

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