Carbonate, carbamate, thiocarbonate dithiocarbonate and...

Details Carbonate, carbamate, thiocarbonate dithiocarbonate and... Carbonate, carbamate, thiocarbonate dithiocarbonate and...

1994-08-18

2002-10-15

Stockton, Laura L. (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C514S352000, C514S478000, C514S484000, C514S487000, C514S522000, C514S533000, C504S304000, C504S225000, C504S260000, C544S164000, C546S309000, C558S233000, C558S245000, C558S248000, C558S270000, C558S273000, C558S393000

Reexamination Certificate

active

06465457

ABSTRACT:

The present invention relates to carbonate, carbamate, thiocarbonate, dithiocarbonate and thiocarbamate derivatives that are useful as fungicides, to processes for preparing them, to compositions containing them and to methods of using them to combat fungi, especially fungal infections of plants.
According to the present invention there is provided a compound having the general formula (I), wherein W is CH
3
OCH═CCO
2
CH
3
, CH
3
ON═CCONR
3
R
4
or CH
3
ON═CCO
2
CH
3
and stereoisomers thereof; n is 0 or 1; X is oxygen or sulphur; Z is oxygen, sulphur or NR
1
; R
1
is hydrogen or alkyl optionally substituted with halogen, C
1-6
alkoxy, C
2-6
alkenyl, C
2-6
alkynyl, C
3-6
cycloalkyl or aryl; R
2
is alkyl, haloalkyl, alkenyl, alkynyl, alkoxycarbonyl(C
1-4
)alkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted aryl(C
1-4
)alkyl, optionally substituted heteroaryl(C
1-4
)alkyl, optionally substituted aryloxy(C
1-4
)alkyl, optionally substituted heteroaryloxy(C
1-4
)alkyl, optionally substituted aryloxy(C
2-4
)alkenyl, optionally substituted heteroaryloxy-(C
2-4
)alkenyl, optionally substituted aryl(C
2-4
)alkenyl, optionally substituted heteroaryl(C
2-4
)alkenyl, optionally substituted arylcarbonyl-(C
1-4
)alkyl, optionally substituted heteroarylcarbonyl(C
1-4
)alkyl, optionally substituted aryloxycarbonyl-(C
1-4
)alkyl, optionally substituted heteroaryloxycarbonyl(C
1-4
)alkyl or —COR
5
; or R
1
and R
2
together form an optionally substituted 4-, 5- or 6-membered heterocyclic ring system; R
3
and R
4
are independently hydrogen or methyl; and R
5
is optionally substituted heteroaryl or optionally substituted aryl; provided that when W is CH
3
O.CH═CCO
2
CH
3
, n is 1 and X and Z are both oxygen then R
2
is not optionally substituted aryl.
Because the double bond of the propenoate, oxyiminoacetamide or oxyiminoacetate group is unsymmetrically substituted, the compounds of the invention may be obtained in the form of mixtures of (E)- and (Z)-geometric isomers. However, these mixtures can be separated into individual isomers, and this invention embraces such isomers and mixtures thereof in all proportions including those which consist substantially of the (Z)-isomer and those which consist substantially of the (E)-isomer. The (E)-isomers are the more fungicidally active and form a preferred embodiment of the invention.
When W is CH
3
ON═CCONR
3
R
4
it is preferred that R
3
is hydrogen and that R
4
is methyl.
Aryl is preferably phenyl.
Heteroaryl includes 5- and 6-membered aromatic rings containing one or more heteroatoms selected from the list comprising oxygen, sulphur and nitrogen and can be fused to benzenoid ring systems. Examples of heteroaryl are pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, indolinyl, isoindolinyl, benzofuranyl, benzothiophenyl and benzimidazolinyl.
Examples of the heterocyclic ring system which can be formed by R
1
and R
2
are pyrrole, pyrrolidine, thiomorpholine, indoline, azetidine, indole, isoindole, imidazole, piperidine, morpholine, benzimidazole and pyrazole. These ring systems are unsubstituted, or substituted as for heteroaryl.
Substitutents which may be present in optionally substituted aryl and heteroaryl moieties include one or more of the following: halo, hydroxy, mercapto, C
1-4
alkyl (especially methyl and ethyl), C
2-4
alkenyl (especially allyl), C
2-4
alkynyl (especially propargyl), C
1-4
alkoxy (especially methoxy), C
2-4
alkenyloxy (especially allyloxy), C
2-4
alkynyloxy (especially propargyloxy), halo(C
1-4
)alkyl (especially trifluoromethyl), halo(C
1-4
)alkoxy (especially trifluoromethoxy), C
1-4
alkylthio (especially methylthio), hydroxy(C
1-4
)alkyl, C
1-4
alkoxy(C
1-4
)-alkyl, C
3-6
cycloalkyl, C
3-6
cycloalkyl(C
1-4
)alkyl, optionally substituted methylenedioxy (especially optionally substituted with fluorine or C
1-4
alkyl), optionally substituted aryl (especially optionally substituted phenyl), optionally substituted heteroaryl (especially optionally substituted pyridyl or pyrimidinyl), optionally substituted heterocyclyl (especially optionally substituted pyrrolidine), optionally substituted aryloxy (especially optionally substituted phenoxy), optionally substituted heteroaryloxy (especially optionally substituted pyridyloxy or pyrimidinyloxy), optionally substituted aryl(C
1-4
)alkyl (especially optionally substituted benzyl, optionally substituted phenethyl and optionally substituted phenyl n-propyl) in which the alkyl moiety is optionally substituted with hydroxy, optionally substituted heteroaryl-(C
1-4
)alkyl (especially optionally substituted pyridyl- or pyrimidinyl-(C
1-4
)alkyl), optionally substituted aryl(C
2-4
)alkenyl (especially optionally substituted phenylethenyl), optionally substituted heteroaryl-(C
2-4
)alkenyl (especially optionally substituted pyridylethenyl or pyrimidinylethenyl), optionally substituted aryl(C
1-4
)alkoxy (especially optionally substituted benzyloxy), optionally substituted heteroaryl(C
1-4
)-alkoxy (especially optionally substituted pyridyl- or pyrimidinyl(C
1-4
)-alkoxy), optionally substituted aryloxy(C
1-4
)alkyl (especially phenoxy-methyl), optionally substituted heteroaryloxy(C
1-4
)alkyl (especially optionally substituted pyridyloxy- or pyrimidinyloxy(C
1-4
)alkyl), acyloxy (including C
1-4
alkanoyloxy (especially acetyloxy) and benzoyloxy), cyano, thiocyanato, nitro, —NR′R″, —NHCOR′, —NHCONR′R″, —CONR′R″, —COOR′, —OSO
2
R′, —SO
2
R′, —COR′, —CR═NR″ or —N═CR′R″ in which R′ and R″ are independently hydrogen, C
1-4
alkyl, C
1-4
alkoxy, C
1-4
alkylthio, C
3-6
cycloalkyl, C
3-6
cycloalkyl(C
1-4
)alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C
1-4
alkyl or C
1-4
alkoxy; when R′ and R″ are in CONR′R″ they can together form a 5- or 6-membered heterocyclic ring (for example a pyrrole, imidazole, pyrrolidine, piperidine or morpholine ring); or two substituents, when they are in adjacent positions on the aryl or heteroaryl ring can join to form a fused alphatic ring (especially to form a fused 6-membered carbon aliphatic ring).
Substituents which may be present in the aryl or heteroaryl rings of any of the foregoing substituents include one or more of the following: halo, hydroxy, mercapto, C
1-4
alkyl, C
2-4
alkenyl, C
2-4
alkynyl, C
1-4
alkoxy, C
2-4
alkenyloxy, C
2-4
alkynyloxy, halo(C
1-4
)alkyl, halo(C
1-4
)alkoxy, C
1-4
alkylthio, hydroxy(C
1-4
)alkyl, C
1-4
alkoxy(C
1-4
)alkyl, C
3-6
cycloalkyl, C
3-6
cycloalkyl(C
1-4
)alkyl, alkanoyloxy, benzoyloxy, cyano, thiocyanato, nitro, —NR′R″, —NHCOR′, —NHCONR′R″, —CONR′R″, —COOR′, —SO
2
R′, —OSO
2
R′, —COR′, —CR═NR″ or —N═CR′R″ in which R′ and R″ have the meanings given above.
All alkyl moieties and the alkyl moiety of alkoxy preferably contain from 1 to 6, more preferably from 1 to 4, carbon atoms. They can be in the form of straight or branched chains, for example methyl, ethyl, n- or iso-propyl, or n-, sec-, iso- or tert-butyl.
Alkenyl and alkynyl moieties preferably contain from 2 to 6, more preferably from 2 to 4, carbon atoms. They can be in the form of straight or branched chains, and the alkenyl moieties, where appropriate, may have either the (E)- or (Z)-configuration. Examples are vinyl, allyl and propargyl.
Halogen is typically fluorine, chlorine or bromine.
In one aspect the present invention provides a compound of formula (I) wherein W is CH
3
O.CH═CCO
2
CH
3
.
In another aspect the present invention provides a compound of formula (I) wherein R
2
is optionally substituted phenyl (especially phenyl substituted by halogen, hydroxy, alkyl, haloalkyl, alkoxy,

Affiliated with

Also associated with

Rating

Carbonate, carbamate, thiocarbonate dithiocarbonate and... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Carbonate, carbamate, thiocarbonate dithiocarbonate and..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Carbonate, carbamate, thiocarbonate dithiocarbonate and... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3000509