Fungicides

Details Fungicides Fungicides

2003-06-27

2004-08-17

Davis, Zinna Northington (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C514S252010, C514S252020, C514S252030, C514S252040, C514S252050, C544S182000, C544S239000, C544S240000, C544S238000

Reexamination Certificate

active

06777412

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 of plants.
A range of pesticidal alkyl 2-(substituted)pyridinyl- and pyrimidinyloxyphenyl-3-alkoxypropenoates is described in EP-A-0242081.
The present invention provides a compound having the formula (I), and stereoisomers thereof, in which any two of K, L and H are nitrogen and the other is CB; T is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heterocyclyl; X is O, S(O)
n
, NR
4
, N(CHO), CR
1
R
2
, CHR
5
, CO, CR
1
(OR
2
), C═CR
1
R
2
, CHR
1
CHR
2
, CR
1
═CR
2
, CHR
1
CR
2
═CH, C≡C, OCHR
1
, CHR
1
O, CH(CF
3
)O, CH(CN)O, OCHR
1
O, S(O)
n
CHR
1
, S(O)
n
CHR
1
O, CHR
1
S(O)
n
, CHR
1
OSO
2
, NR
4
CHR
1
, CHR
1
NR
4
, CO
2
, O
2
C, SO
2
O, OSO
2
, CO.CO, COCHR
1
, COCHR
1
O, CHR
1
CO, CHOH.CHR
1
, CHR
1
.CHOH, &PSgr;, Q (for the meaning of &PSgr; and Q, see under “Chemical Formulae” later), CONR
4
, OCONR
4
, NR
4
CO, CSNR
4
, OCS.NR
4
, SCO.NR
4
, NR
4
CO
2
, NR
4
CS, NR
4
CSO, NR
4
COS, NR
4
CONR
4
, S(O)
n
NR
4
, NR
4
S(O)
n
, CS
2
, S
2
C, CO.S, SCO, N═N, N═CR
1
, CR
1
═N, CHR
1
CHR
2
CH(OH), CHR
1
OCO, CHR
1
SCO, CHR
1
NR
4
CO, CHR
1
NR
4
CONR
4
, CHR
1
CHR
2
CO, CR
1
NO, C(NR
1
R
2
)═NO, ON═CR
1
, ON═C(NR
1
R
2
), CHR
1
ON═CR
2
, CO.OCR
1
R
2
, CHR
1
CHR
2
CHR
3
, OCHR
1
CHR
2
, (CH
2
)
m
O, CHR
1
OCHR
2
, CHR
1
CHR
2
O, OCHR
1
CHR
2
O, S(O)
n
CHR
1
CHR
2
, SCHR
1
CHR
2
O, CHR
1
S(O)
n
CHR
2
, CHR
1
CHR
2
S(O)
n
, CR
1
═NNR
4
, NR
4
N═CR
1
, CHR
1
CONR
2
, CHR
1
OCO.NR
2
, CH═CHCH
2
O, C≡CCH
2
O, COCHR
1
CHR
2
O, or (R
5
)
2
P
+
CHR
2
O
−
; A, B and E, which may be the same or different, are H, hydroxy, halo, C
1-4
alkyl, C
1-4
alkoxy, C
1-4
haloalkyl, C
1-4
haloalkoxy, C
1-4
alkylcarbonyl, C
1-4
alkoxycarbonyl, phenoxy, nitro or cyano; R
1
, R
2
and R
3
, which may be the same or different, are H, C
1-4
alkyl or phenyl; R
4
is H, C
1-4
alkyl or COR
1
; R
5
is optionally substituted phenyl; O
−
is a halide anion; n is 0, 1 or 2, m is 3, 4 or 5, and q is 0 or 1; provided that when q is 0 and Z is an optionally substituted 3- to 6-membered heterocyclic ring containing at least one trivalent nitrogen atom, Z is not attached to the central pyrimidine ring by said trivalent nitrogen atom, and that when q is 1 and X is 0, Z is not optionally substituted phenyl or optionally substituted pyridinyl.
Because the double bond of the propenoate group is unsymmetrically substituted, the compounds of the invention may be obtained in the form of mixtures of (E)- and (Z)-geometric is mers. 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)-isomer, in which the groups —CO
2
CH
3
and —OCH
3
are on opposite sides of the olefinic bond of the propenoate group, are the more fungicidally active and form a preferred embodiment of the invention.
The substituent Z in compound (I) is optionally substituted aryl or optionally substituted heterocyclyl. Where valency allows, each of the optionally substituted groups aryl or heterocyclyl can carry up to 5 substitutents. The term “aryl” includes phenyl in particular, and naphthyl. The term “heterocyclyl” includes 5- and 6-membered heterocyclic groups containing one or more of each of the heteroatoms O, S and N (preferably S or N), fused benzenoid and heteroaromatic ring systems, and, in each case, the corresponding N-oxides. Examples of heterocyclyl groups which Z may be, except where otherwise indicated, are pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,2,3-, 1,2,4-, and 1,3,5-triazinyl, 1,2,4,5-tetrazinyl, 1,2,3- and 1,2,4-triazolyl, imidazolyl, thienyl, furyl, pyrrolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, 1,2,4- and 1,3,5-thiadiazolyl, oxadiazolyl, purinyl, quinolinyl, isoquinolinyl, quinoxalinyl, benzothienyl, benzoxazolyl, benzthiazolyl, piperidinyl, morpholinyl, pyrrolidinyl and tetrahydrofuranyl, and, where appropriate, the corresponding N-oxides. Substituents which may be present in the optionally substituted aryl and heterocyclyl moieties include one or more of the following; halo, hydroxy, oxo, 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), C
2-4
alkenylthio, 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 aryl (especially optionally substituted phenyl), optionally substituted heterocyclyl (especially optionally substituted pyridinyl or pyrimidinyl), optionally substituted aryloxy (especially optionally substituted phenoxy), optionally substituted phenylthio, 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, pyrimidinylethenyl or 1-(imidazol-1-yl)vinyl), optionally substituted aryl(C
1-4
)alkoxy (especially optionally substitued 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 phenoxymethyl), optionally substituted heteroaryloxy(C
1-4
)alkyl (especially optionally substituted pyridinyloxy- or pyrimidinyloxy(C
1-4
)-alkyl), acyloxy, including C
1-4
alkanoyloxy (especially acetyloxy) and benzoyloxy, cyano, isocyano, thiocyanato, isothiocyanato, nitro, —NR′R″, —N
3
, —NHCONR′R″, —NR′COR″, —CONR′R″, CR′═NOR″, CHR′CO
2
R″, CSNR′R″, —CO
2
R′, —OSO
2
R′, —SO
2
R′, —SOR′, SO
2
OR′, SO
2
NR′R″, —COR′, —OCOR′, —CR′═NR″, N═CHNR′R″, NHSO
2
R′ or —N═CR′R″ in which R′ and R″ are independently hydrogen, hydroxy, C
1-4
alkyl, C
1-4
alkoxy, C
1-4
alkylthio, C
3-6
cycloalkyl, C
3-6
cycloalkyl(C
1-4
)alkyl, C
2-4
alkenyl, C
2-4
alkenyloxy, phenyl, phenoxy or benzyl, the phenyl, phenoxy and benzyl groups being optionally substituted with halogen, C
1-4
alkyl or C
1-4
alkoxy, or two substituents when ortho to one another join to form a 5- or 6-membered aliphatic or aromatic ring optionally containing one or more oxygen, sulphur or nitrogen atoms.
Substituents which may be present in the aryl or heterocyclyl rings of any of the foregoing substituents and in the phenyl ring of R
5
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, benzyloxy, cyano, thiocyanato, nitro, —NR′R″, —NHCOR′, —NHCONR′R″, —CONR′R″, —CO
2
R′, —OSO
2
R′, —SO
2
R′, —COR′, —CR′&

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