Hetero-aryl compounds having herbicidal, fungicidal and...

Details Hetero-aryl compounds having herbicidal, fungicidal and... Hetero-aryl compounds having herbicidal, fungicidal and...

1995-03-27

2003-11-25

Rotman, Alan L. (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S244000, C504S314000, C544S298000, C544S303000, C544S305000, C544S315000, C544S318000, C546S296000, C546S297000, C546S301000, C560S060000, C560S043000, C514S256000, C514S277000, C514S570000

Reexamination Certificate

active

06653258

ABSTRACT:

This invention relates to derivatives of propenoic acid useful as fungicides, to processes for preparing them, to fungicidal compositions containing them, and to methods of using them to combat fungi, especially fungal infections in plants.
The invention provides a compound having the formula (I):
and stereoisomers thereof, wherein R
1
is optionally substituted aryl or optionally substituted heteroaryl; Y is oxygen, sulphur or NR
4
; R
2
, R
3
and R
4
, which may be the same or different, are hydrogen, C
1-4
alkyl or C
2-4
alkenyl; X is halogen (fluorine, chlorine, bromine or iodine), C
1-4
alkyl, C
2-4
alkenyl, C
1-4
alkoxy, nitro or cyano; and n is 0 or an integer of 1 to 4; provided that when Y is oxygen, n is 0 and R
1
is unsubstituted phenyl at least one of R
2
and R
3
is other than hydrogen or methyl.
In one aspect the invention provides compounds of the formula (I) as defined above in which Y is oxygen.
In another aspect the invention provides compounds of the formula (I) as defined above in which R
1
is optionally substituted hereroaryl.
In still another aspect the invention provides compounds of the formula (I) as defined above in which R
1
is optionally substituted aryl and Y is NR
4
.
In yet another aspect the invention provides compounds of the formula (I) as defined above in which R
1
is optionally substituted aryl, Y is oxygen or sulphur but R
2
and R
3
are not both hydrogen.
In yet another aspect the invention provides compounds of the formula (I) as defined above in which X is C
2-4
alkenyl.
The compounds of the invention contain at least one carbon-carbon double bond, and are sometimes obtained in the form of mixtures of 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 individual isomers which result from the unsymmetrically substituted double bond of the propenoate group are identified by the commonly used terms “(E)” and “(Z)”. These terms are defined according to the Cahn-Ingold-Prelog system which is fully described in the literature (see, for example, J March, “Advanced Organic Chemistry”, 3rd edition, Wiley-Interscience, page 109 et seq).
Usually one isomer is more active fungicidally than the other, the more active isomer usually being the one wherein the groups —CO
2
CH
3
and —OCH
3
are on opposite sides of the olefinic bond of the propenoate group (the (E)-isomer). These (E)-isomers form a preferred embodiment of the invention.
The substituent R
1
in compound (I) is optionally substituted aryl or optionally substituted heteroaryl. The term “aryl” includes phenyl in particular, and naphthyl. The term “heteroaryl” includes 5- and 6-membered heterocyclic groups containing one or more of each of the heteroatoms O, S and N (preferably S or N), and fused benzenoid and heteroaromatic ring systems. Examples of heteroaryl groups which R
1
may be are pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,2,3-, 1,2,4-, and 1,3,5-triazinyl, 1,2,4,5-tetrazinyl, thienyl, quinolinyl, isoquinolinyl, quinoxalinyl and benzothienyl.
Substituents which may be present in the optionally substituted aryl and heteroaryl moieties include one or more of the following; halogen, hydroxy, 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, trichloromethyl, and chloro- and bromomethyl), halo(C
1-4
)alkoxy (especially trifluoromethoxy), C
1-4
alkylthio (especially methylthio), hydroxy(C
1-4
)alkyl (especially hydroxymethyl), (C
1-4
)alkoxy(C
1-4
)alkyl, C
3-6
cycloalkyl, C
3-6
cycloalkyl(C
1-4
)alkyl, optionally substituted aryl (especially optionally substituted phenyl), optionally substituted heteroaryl (especially optionally substituted pyridinyl or pyrimidinyl), optionally substituted aryloxy (especially optionally substituted phenoxy), optionally substituted heteroaryloxy (especially optionally substituted pyridinyloxy 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 pyridinyl- 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 pyridinylethenyl or pyrimidinylethenyl), optionally substituted aryl(C
1-4
)alkoxy (especially optionally substituted benzyloxy), optionally substituted heteroaryl(C
1-4
)alkoxy (especially optionally substituted pyridinyl- or pyrimidinyl(C
1-4
)alkoxy), optionally substituted aryloxy (C
1-4
)alkyl (especially optionally substituted phenyloxymethyl), optionally substituted heteroaryloxy(C
1-4
)alkyl (especially optionally substituted pyridinyl- or pyrimidinyloxy(C
1-4
)-alkyl), acyloxy (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, optionally substituted aryl (especially optionally substituted phenyl) or optionally substituted aryl(C
1-4
)alkyl (especially optionally substituted benzyl). Substituents which may be present in the optionally substituted aryl and heteroaryl moieties include one or more of those aryl and heteroaryl substituents described immediately above.
Therefore, in yet another aspect, the invention provides compounds of the formula (I) as defined above in which R
1
is aryl optionally substituted with one or more of hydroxy, C
3-6
cycloalkyl(C
1-4
)alkyl, aryl(C
1-4
)alkoxy, aryloxy(C
1-4
)alkyl, acyloxy, CR′═NR″ or N═CR′R″ and R′ and R″ are independently hydrogen, 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.
In yet another aspect the invention provides compounds of the formula (I) as defined above in which R
1
is aryl optionally substituted with one or more of NR′R″, NHCOR′, NHCONR′R″, CONR′R″, CO
2
R′, OSO
2
R′, SO
2
R′ or COR′, R′ is C
3-6
cycloalkyl(C
1-4
)alkyl or benzyl and R″ is hydrogen, 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.
In yet another aspect the invention provides the (E)-isomers of the compounds of the formula (Ia):
in which A
b
is selected from the group comprising 2-bromo; 3-iodo; 2-ethyl; 3-iso-propyl; 3-t-butyl; 3-trifluoro-methoxy; 3-amino; 4-phenyl; 2-carboxy; 3-methoxycarbonyl; 2-hydroxy; 2,3-difluoro; 3,5-difluoro; 2,3-dimethoxy; 2-fluoro-4-chloro; 2-chloro-5-fluoro; 2-fluoro-6-methyl; 3-methyl-4-fluoro; 3-fluoro-5-methoxy; 2-methoxy-3-fluoro; 2-chloro-4-methyl; 2-methyl-5-chloro; 2-chloro-6-methoxy; 3-methoxy-4-chloro; 3-methyl-5-methoxy; 2,4,5-trifluoro; 2,4,6-trichloro; 2,4,6-trimethyl; 2,6-difluoro-4-chloro; 2,6-dimethyl-4-fluoro, 2,3,5,6-tetrachloro; pentafluoro; and pentachloro.
Where substituents in the aryl or heteroaryl moieties are in adjacent positions they may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more hetero atoms. Examples of R
1
where substituents join to

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