Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1999-10-14
2002-02-05
Higel, Floyd D. (Department: 1613)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C514S341000, C514S369000, C514S386000, C514S398000, C546S278700, C548S316700, C548S317100, C548S315100
Reexamination Certificate
active
06344564
ABSTRACT:
The present invention relates to novel fungicidal imidazolinone and imidazolinethione compounds for use in plant protection. It also relates to the processes for the preparation of said compounds and to the compounds which can optionally be used as intermediates in the preparation processes. It further relates to the use of these compounds as fungicides, to fungicidal compositions comprising these compounds and to methods for combating fungal diseases in crops using these compounds.
One object of the present invention is to provide compounds showing improved properties in the treatment of fungal diseases.
Another object of the present invention is to provide compounds showing a spectrum of use in the field of fungal diseases which is also improved.
In a first major aspect of the present invention, it has been found that these objects can be achieved by virtue of compounds of the invention which are 2-imidazolin-5-one and 2-imidazoline-5-thione derivatives of the general formula (I):
wherein:
W is a s or oxygen atom or an S═O group;
A represents O or S;
n=0 or 1;
B represents NR
5
or O or S or CR
5
R
6
or SO
2
or C═O;
R
1
and R
2
, which are identical or different represent:
H, provided that one of the two groups is different from H;
an alkyl or haloalkyl radical having 1 to 6 carbon atoms;
an alkoxyalkyl, alkylthioalkyl, alkylsulfonylalkyl, monoalkylaminoalkyl, alkenyl or alkynyl radical having 2 to 6 carbon atoms;
a dialkylaminoalkyl or cycloalkyl radical having 3 to 7 carbon atoms;
an aryl radical comprising phenyl, naphthyl, thienyl, furyl, pyridyl, benzothienyl, benzofuryl, quinolyl, isoquinolyl or methylenedioxyphenyl, optionally substituted by 1 to 3 groups chosen from R
7
; or
an arylalkyl, aryloxyalkyl, arylthioalkyl or arylsulfonylalkyl radical, the terms aryl and alkyl having the definitions given above;
or R
1
and R
2
can form, with the carbon to which they are bonded on the ring, a carbocycle or a heterocycle having from 5 to 7 atoms, it being possible for these rings to be fused to a phenyl, optionally substituted by 1 to 3 groups chosen from R
7
;
R
3
represents:
an alkyl group having 1 to 6 carbon atoms;
an alkoxyalkyl alkyl1thioalkyl, alkysulfonylalkyl, haloalkyl, cyanoalkyl, thiocyanatoalkyl, oxoalkyl, alkenyl or alkynyl group having 2 to 6 carbon atoms;
a dialkylaminoalkyl, alkoxycarbonylalkyl or N-alkylcarbamaoylalkyl group having 3 to 6 carbon atoms;
a N,N-dialkylcarbamoylalkyl group having 4 to 8 carbons atoms; or
an arylalkyl group, the alkyl part being a radical having 1 to 6 carbon atoms and the aryl part being phenyl, naphthyl, thienyl, furyl or pyridyl, optionally substituted by 1 to 3 groups chosen from R
7
;
R
4
represents:
a hydrogen atom (when n is equal to 1);
an alkyl group having 1 to 6 carbon atoms;
an alkoxyalkyl, alkylthioalkyl, haloalkyl, cyanoalkyl, thiocyanatoalkyl, alkenyl or alkynyl group having 2 to 6 carbon atoms;
a dialkylaminoalkyl, alkoxycarbonylalkyl or N-alkylcarbamoylalkyl group having 3 to 6 carbon atoms;
a N,N-dialkyl carbamoylalkyl group having 4 to 8 carbon atoms;
an aryl radical, comprising phenyl, naphthyl, thienyl, furyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, benzothienyl, benzofuryl, quinolyl, isoquinolyl or methylenedioxyphenyl, optionally substituted by 1 to 3 groups chosen from R
7
;
an arylalkyl, aryloxyalkyl, arylthioalkyl or arylsulfonylalkyl radical, the terms aryl and alkyl having the definitions given above;
an amino group disubstituted by two identical or different groups chosen from:
an alkyl radical having 1 to 6 carbon atoms;
an alkoxyalkyl, alkenyl or alkynyl radical having 3 to 6 carbon atoms;
a cycloalkyl radical having 3 to 7 carbon atoms;
an arylalkyl, such as defined above, phenyl or naphthyl radical, optionally substituted by 1 to 3 groups chosen from R
7
; and
a thienylmethyl or furfuryl radical; or
a pyrrolidino, piperidino, morpholino or piperazino group, optionally substituted by aryl having 1 to 3 carbon atoms;
R
5
represents:
H, except when R
4
is H;
an alkyl, haloalkyl, alkylsulfonyl or haloalkylsulfonyl radical having 1 to 6 carbon atoms;
an alkoxyalkyl, alkylthioalkyl, acyl, alkenyl, alkynyl, haloacyl, alkoxycarbonyl, haloalkoxycarbonyl, alkoxyalkylsulfonyl or cyanoalkylsulfonyl radical having 2 to 6 carbon atoms;
an alkoxyalkoxycarbonyl, alkylthioalkoxycarbonyl or cyanoalkoxycarbonyl radical having 3 to 6 carbon atoms;
a formyl radical;
a cycloalkyl, alkoxyacyl, alkylthioacyl, cyanoacyl, alkenylcarbonyl or alkynylcarbonyl radical having 3 to 6 carbon atoms;
a cycloalkylcarbonyl radical having 4 to 8 carbon atoms;
a phenyl; arylalkylcarbonyl, especially phenylacetyl or phenylpropionyl; arylcarbonyl, especially benzoyl, optionally substituted by 1 to 3 groups chosen from R
7
; thienylcarbonyl; furylcarbonyl; pyridylcarbonyl; benzyloxycarbonyl; furfuryloxycarbonyl; tetrahydrofurfuryloxycarbonyl; thienylmethoxycarbonyl; pyridylmethoxycarbonyl; phenoxycarbonyl or (phenylthio)carbonyl, the phenyl being itself optionally substituted by 1 to 3 groups chosen from R
7
; (alkylthio)carbonyl; (haloalkylthio)carbonyl; (alkoxyalkylthio)carbonyl; (cyanoalkylthio)carbonyl; (benzylthio)carbonyl; (furfurylthio)carbonyl; (tetrahydrofurfurylthio)carbonyl; (thienylmethylthio)carbonyl; (pyridylmethylthio)carbonyl; or arylsulfonyl radical;
a carbamoyl radical, optionally mono- or disubstituted by:
an alkyl or haloalkyl group having 1 to 6 carbon atoms;
a cycloalkyl, alkenyl or alkynyl group having 3 to 6 carbon atoms;
an alkoxyalkyl, alkylthioalkyl or cyanoalkyl group having 2 to 6 carbon atoms; or
a phenyl, optionally substituted by 1 to 3 R
7
groups;
a sulfamoyl group, optionally mono- or disubstituted by:
an alkyl or haloalkyl group having 1 to 6 carbon atoms;
a cycloalkyl, alkenyl or alkynyl group having 3 to 6 carbon atoms;
an alkoxyalkyl, alkylthioalkyl or cyanoalkyl group having 2 to 6 carbon atoms; or
a phenyl, optionally substituted by 1 to 3 R
7
groups; or
an alkylthioalkylsulfonyl group having 3 to 8 carbon atoms or a cycloalkylsulfonyl group having 3 to 7 carbon atoms;
R
6
represents:
a hydrogen atom;
a cyano group;
an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 7 carbon atoms;
an acyl or alkoxycarbonyl group having 2 to 6 carbon atoms; or
a benzoyl group, optionally substituted by 1 to 3 R
7
groups; and
R
7
represents:
a halogen atom;
an alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio or alkylsulfonyl radical having 1 to 6 carbon atoms;
a cycloalkyl, halocycloalkyl, alkenyloxy, alkynyloxy, alkenylthio or alkynylthio radical having 3 to 6 carbon atoms;
a nitro or cyano group;
an amino radical, optionally mono- or disubstituted by an alkyl or acyl radical having 1 to 6 carbon atoms or an alkoxycarbonyl radical having 2 to 6 carbon atoms; or
a phenyl, phenoxy or pyridyloxy radical, these radicals optionally being substituted;
and the corresponding agriculturally acceptable salts.
Certain specific compounds of the formula (I), having the formula (Ia):
wherein W, R
1
to R
6
and n have the same meaning as in formula (I), are known. Denoted S-alkylated derivatives of 5,5diphenyl-2-thiohydantoin and of 5,5-diphenyldithiohydrantoin, those particular compounds have been especially studied for their pharmacological properties, as described in:
(a) Zejc, A.,
Dissertations Pharmaceuricae er pharmacologicae, Warsaw,
20 (5), 507-524 and 525-537 (1968);
(b) Lucka-Sobstel, B. and Zejc, A.,
Dissertationes Pharmaceuticae er pharmacologicae,
22 (1), 13-19 (1970); and
(c) Fetter, J., Harsanyi, K, Nyitrai, J. and Lempert, K.,
Acta Chemica
(
Budapest
), 78 (3), 325-333 (1973).
No agricultural fungicidal activity has been previously described for these compounds.
Other specific compounds of formula (I) have been described by (d) Bohme, Martin and Strahl in
Archiv der Pharmazie,
313, 10-15 (1980). They are the three compounds of the formula:
wherein R is H, CH
3
or phenyl. These compounds are thus included in the compounds of formula (Ib), which form part of the invention:
wherein W and R
1
to R
5
have the same meaning as in fo
Bascou Jean-Philippe
Emeric Gilbert
Gadras Alain
Lacroix Guy
Peignier Raymond
Higel Floyd D.
Rhone-Poulenc Inc.
LandOfFree
Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2984769