Benzazoles: benzoxazole, benzthiazole and benzimidazole...

Details Benzazoles: benzoxazole, benzthiazole and benzimidazole... Benzazoles: benzoxazole, benzthiazole and benzimidazole...

2001-01-23

2003-04-08

Shah, Mukund J. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C548S159000, C548S206000, C544S133000, C514S367000, C514S372000

Reexamination Certificate

active

06544989

ABSTRACT:

The present invention relates to isothiazole derivatives, to processes for preparing them, to fungicidal, insecticidal, acarcidal, molluscicidal and nematicidal compositions comprising them, to methods of using them to combat fungal diseases (especially fungal diseases of plants) and to methods of using them to combat and control insect, acarine, mollusc and nematode pests.
Isothiazole derivatives are disclosed in WO 95/31448, WO 97/18198, WO 98/02424 and WO 98/05670.
The present invention provides a compound of formula (I):
wherein X is O or S; n is 0 or 1; Y is O, S or NR
7
; R
1
is hydrogen, halogen, C
1-6
alkyl, C
1-6
haloalkyl, C
1-6
alkoxy, C
1-6
haloalkoxy, C
1-6
alkylthio, C
1-6
haloalkylthio, C
3-6
cycloalkyl, C
1-6
alkoxy(C
1-6
)alkyl or SF
5
; R
2
is hydrogen, halogen, C
1-6
alkyl, C
1-6
alkoxy, C
1-6
haloalkoxy, C
1-6
alkylthio, C
1-6
haloalkylthio, C
1-6
alkylsulfinyl, C
1-6
haloalkylsulfinyl, C
1-6
alkylsulfonyl, C
-6
haloalkylsulfonyl, C
1-6
haloalkyl, cyano, nitro, CHO, CH═NOR
5
, C
1-6
alkylcarbonyl, C
1-6
alkoxycarbonyl or SF
5
; or together R
1
and R
2
form a five or six merbered saturated or unsaturated carbocyclic ring, optionally substituted by one or two C
1-6
alkyl groups; R
3
is hydrogen, C
1-6
alkyl, CH
2
(C
1-4
haloalkyl), C
1-6
cyanoalkyl, C
3-6
alkenyl, C
3-6
alkynyl, C
1-6
alkoxy(C
1-6
)alkyl, C
1-6
alkylthio(C
1-6
)alkyl, C
1-6
alkoxy(C
1-6
)alkoxy(C
1-6
)alkyl, C
1-6
alkylcarbonyl, C
1-6
alkoxycarbonyl, formyl, C
1-6
alkylcarbonyl(C
1-6
)alkyl, C
1-6
alkoxycarbonyl(C
1-6
)alkyl, C
1-6
alkylaminocarbonyl, di(C
1-6
)alkylaminocarbonyl, optionally substituted phenoxycarbonyl, optionally substituted phenyl(C
1-4
)alkyl or S(O)
q
R
6
; R
4
is hydrogen, halogen, cyano, C
1-8
alkyl, C
1-6
haloalkyl, C
1-6
cyanoalkyl, C
2-6
alkenyl, C
2-6
alkynyl, C
3-7
cycloalkyl, C
3-7
halocycloalkyl, C
3-7
cyanocycloalkyl, C
1-3
alkyl(C
3-7
)cycloalkyl, C
1-3
alkyl(C
3-7
)halocycloalkyl, C
3-6
cycloalkyl(C
1-6
)alkyl, C
5-6
cycloalkenyl, C
5-6
cycloalkenyl(C
1-6
)alkyl, C
1-6
haloalkenyl, C
1-6
cyanoalkenyl, C
1-6
alkoxy(C
1-6
)alkyl, formyl, C
1-6
carboxyalkyl, C
1-6
akylcarbonyl(C
1-6
)alkyl, C
1-6
alkoxycarbonyl(C
1-6
)alkyl, C
1-6
alkylthio(C
1-6
)alkyl, C
1-6
alkylsulfinyl(C
1-6
)alkyl, C
1-6
alkylsulfonyl(C
1-6
)alkyl, aminocarbonyl(C
1-6
)alkyl, C
1-6
alkylaminocarbonyl(C
1-6
)alkyl, di(C
1-6
)alkylaminocarbonyl(C
1-6
)alkyl, C
1-6
alkoxycarbonyl, C
1-6
alkylcarbonyl, aminocarbonyl, C
1-6
alkylaminocarbonyl, di(C
1-6
)alkylaminocarbonyl, optionally substituted phenyl, optionally substituted phenyl(C
1-4
)alkyl, optionally substituted phenyl(C
2-4
)alkenyl, optionally substituted heteroaryl, optionally substituted heteroaryl(C
1-4
)alkyl, optionally substituted heterocyclyl, optionally substituted heterocyclyl(C
1-4
)alkyl, a group OR
8
, a group SH, a group S(O)
p
R
9
, a group NR
10
R
11
or a group C(R
12
)═NOR
13
; R
5
is hydrogen, C
1-6
alkyl, optionally substituted phenyl or optionally substituted phenyl(CC
1-4
)alkyl; R
6
is C
1-6
alkyl, C
1-6
haloalkyl or optionally substituted phenyl; R
7
is hydrogen, cyano, C
1-8
alkyl, C
1-6
haloalkyl, C
1-6
cyanoalkyl, C
2-6
alkenyl, C
2-6
alkynyl, C
3-7
cycloalkyl, C
2-6
haloalkenyl, C
3-6
cycloalkyl(C
1-6
)alkyl, C
1-6
alkoxy(C
1-6
)alkyl, C
1-6
alkoxycarbonyl, C
1-6
alkylcarbonyl, C
1-6
alkylaminocarbonyl, di(C
1-6
)alkylaminocarbonyl, optionally substituted phenyl or optionally substituted heteroaryl; R
8
is hydrogen, C
1-6
alkyl, C
1-6
haloalkyl, C
3-6
alkenyl, C
1-4
cyanoalkyl, C
1-6
alkoxycarbonyl(C
1-6
)alkyl, optionally substituted phenyl, optionally substituted phenyl(C
1-4
)alkyl, optionally substituted heteroaryl, N═C(CH
3
)
2
; R
9
is C
1-6
alkyl, C
1-6
haloalkyl, C
3-6
alkenyl, cyano, C
1-4
cyanoalkyl, C
1-6
alkoxycarbonyl(C
1-6
)alkyl, optionally substituted phenyl, optionally substituted phenyl(C
1-4
)alkyl or optionally substituted heteroaryl; R
10
and R
11
are, independently, hydrogen, C
1-8
alkyl, C
3-7
cycloalkyl, C
3-6
alkenyl, C
3-6
alkynyl, C
2-6
haloalkyl, C
1-6
alkoxy(C
1-6
)alkyl, C
1-6
alkoxycarbonyl, optionally substituted phenoxycarbonyl, formyl, C
1-6
alkylcarbonyl, C
1-6
alkylSO
2
, optionally substituted phenylSO
2
or optionally substituted phenyl(C
1-4
)alkyl; R
12
is C
1-3
alkyl; R
13
is C
1-6
alkyl, optionally substituted phenyl(C
1-2
); and p and q are, independently, 0, 1 or 2.
The compounds of formula (I) may exist in different isomeric or tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions.
In a further aspect the present invention provides a compound of formula (I) wherein X is O or S; n is 0 or 1; Y is O, S or NR
7
; R
1
is hydrogen, halogen, C
1-6
alkyl, C
1-6
haloalkyl C
1-6
alkoxy, C
1-6
haloalkoxy, C
1-6
alkylthio, C
3-6
cycloalkyl or C
1-6
alkoxy(C
1-6
)alkyl; R
2
is hydrogen, halogen, C
1-6
alkyl, C
1-6
haloalkyl, cyano, nitro, CHO, CH═NOR
5
, C
1-6
alkylcarbonyl, C
1-6
alkoxycarbonyl or C
1-6
alkylS(O)
x
; or together R
1
and R
2
form a five or six membered saturated or unsated carbocyclic ring, optionally substituted by one or two C
1-6
alkyl groups; R
3
is hydrogen, C
1-6
alkyl, CH
2
(C
1-4
haloalkyl), C
3-6
alkenyl, C
3-6
alkynyl, C
1-6
alkoxy(C
1-6
)alkyl, C
1-6
alkylcarbonyl, C
1-6
alkoxycarbonyl, formyl, optionally substituted phenoxycarbonyl, optionally substituted phenyl(C
1-4
)alkyl or S(O)
y
R
25
; R
4
is hydrogen, halogen, cyano, optionally substituted alkyl, C
1-8
alkoxy, C
1-8
haloalkoxy, C
1-8
alkylthio, C
2-6
alkenyl, C
2-6
alkynyl, C
3-7
cycloalkyl (optionally substituted with halogen or C
1-6
alkyl), C
5-6
cycloalkenyl (optionally substituted with halogen or C
1-6
alkyl), C
2-6
haloalkenyl, NHSO
2
R
24
, NHCOR
24
, CONR
20
R
21
, NR
20
R
21
, COR
24
, CO
2
R
20
, optionally substituted phenyl substituted heteroaryl or a group ZR
26
; R
5
is hydrogen, C
1-6
alkyl, optionally substituted phenyl or optionally substituted phenyl(C
1-4
)alkyl; R
5
is C
1-6
alkyl, C
1-6
haloalkyl or optionally substituted phenyl; Z is O, S, SO, SO
2
or NR
27
; R
7
is hydrogen, cyano, C
1-8
alkyl, C
1-6
haloalkyl, C
1-6
cyanoalkyl, C
2-6
alkenyl, C
2-6
alkynyl, C
3-7
cycloalkyl, C
2-6
haloalkenyl, C
3-6
cycloalkyl(C
1-6
)alkyl, C
1-6
alkoxy(C
1-6
)alkyl, C
1-6
alkoxycarbonyl, C
1-6
alkylcarbonyl, C
1-6
alkylaminocarbonyl, di(C
1-6
)alkylaminocarbonyl, optionally substituted phenyl or optionally substituted heteroaryl; R
26
and R
27
are, independently, hydrogen, C
1-8
alkyl, C
3-6
alkenyl, C
3-6
alkynyl, C
1-6
alkoxy(C
1-6
)alkyl, C
1-6
alkoxycarbonyl, optionally substituted phenoxycarbonyl, C
1-6
alkycarbonyl or optionally substituted phenyl(C
1-4
)alkyl, or R
26
and R
27
join to form a 5- or 6-membered saturated or unsaturated ring optionally containing another heteroatom selected from oxygen, sulfur and nitrogen; R
20
and R
21
are, independently, hydrogen or C
1-6
alkyl; R
24
is C
1-6
alkyl or phenyl; and x and y are, independently, 0, 1 or 2.
Alkyl is straight or branched chain and is, for example, methyl ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl or neo-pentyl.
Halogen is fluorine, chlorine, bromine or iodine.
Haloalkyl groups are alkyl groups which are optionally substituted with one or more of the same or different halogen atoms and are, for example, CF
3
, CH
2
CF
3
or CH
2
CHF
2
.
Phenyl(C
1-4
)alkyl is, for example, 1-phenyleth-1-yl, 2-phenyleth-1-yl, 2-phenylprop-2-yl, 3-phenylprop-1-yl, but is preferably benzyl.
The term heteroaryl refers to an aromatic ring containing one or more heteroatoms (preferably one or two heteroatoms) selected from O, S and N. Examples of such rings include pyridine, pyrimidine, furan, quinazoline, thiophene, thiazole, oxazole and isoxazole.
The term heterocyclyl refers to a non-aromatic ring containing one or more (preferably one or two) heteroatoms selected from O, S and N. Examples of such rings include 1,3-dioxolanyl, te

Affiliated with

Also associated with

Rating

Benzazoles: benzoxazole, benzthiazole and benzimidazole... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Benzazoles: benzoxazole, benzthiazole and benzimidazole..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Benzazoles: benzoxazole, benzthiazole and benzimidazole... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3037487