Organic compounds

Details Organic compounds Organic compounds

1998-05-27

2001-11-06

Barts, Samuel (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

C564S153000, C564S163000, C564S164000, C564S166000, C564S167000, C560S035000, C560S051000, C560S053000, C560S060000, C562S444000, C562S450000, C544S224000, C544S242000, C548S247000, C548S255000

Reexamination Certificate

active

06313344

ABSTRACT:

ORGANIC COMPOUNDS
The invention relates to compounds of formula
wherein either
X is CH or N, Y is OR, and Z is O, or
X is N, Y is NHR
8
and Z is O, S or S(═O);
R
1
is hydrogen or C
1
-C
4
alkyl;
R
8
is hydrogen or C
1
-C
4
alkyl;
R
2
is H, C
1
-C
4
alkyl, halo-C
1
-C
4
alkyl, C
3
-C
6
cycloalkyl, C
1
-C
4
alkoxymethyl, C
1
-C
4
alkoxy, halo-C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, halo-C
1
-C
4
alkylthio or CN;
R
3
and R
4
are each independently of the other H, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, OH, CN, NO
2
, a (C
1
-C
4
alkyl)
3
—Si group, the alkyl groups being the same or different, halogen, (C
1
-C
4
alkyl)S(═O)
m
, (halo-C
1
-C
4
alkyl)S(═O)
m
, halo-C
1
-C
4
alkyl or halo-C
1
-C
4
alkoxy;
m is 0, 1 or 2;
R
5
independently of any other is halogen, C
1
-C
6
alkyl, halo-C
1
-C
6
alkyl, C
3
-C
6
cycloalkyl, halo-C
3
-C
6
cycloalkyl, C
1
-C
6
alkoxy, halo-C
1
-C
6
alkoxy, C
1
-C
6
alkylthio, halo-C
1
-C
6
alkylthio, C
1
-C
6
alkylsulfinyl, halo-C
1
-C
6
alkylsulfinyl, C
1
-C
6
alkylsulfonyl, halo-C
1
-C
6
alkylsulfonyl, C
1
-C
6
alkylsulfonyloxy, halo-C
1
-C
6
alkylsulfonyloxy, C
1
-C
6
alkoxy-C
1
-C
6
alkyl, halo-C
1
-C
6
alkoxy-C
1
-C
6
alkyl, C
1
-C
6
alkylthio-C
1
-C
6
alkyl, halo-C
1
-C
6
alkylthio-C
1
-C
6
alkyl, C
1
-C
6
alkylsulfinyl-C
1
-C
6
alkyl, halo-C
1
-C
6
alkylsulfinyl-C
1
-C
6
alkyl, C
1
-C
6
alkylsulfonyl-C
1
-C
6
alkyl, halo-C
1
-C
6
alkylsulfonyl-C
1
-C
6
alkyl, C
1
-C
6
alkylcarbonyl, halo-C
1
-C
6
alkylcarbonyl, C
1
-C
6
-alkoxycarbonyl, halo-C
1
-C
6
alkoxycarbonyl, C
1
-C
6
alkylaminocarbonyl, C
1
-C
4
alkoxyiminomethyl, di(C
1
-C
6
alkyl)aminocarbonyl, the alkyl groups being the same or different; C
1
-C
6
alkylaminothiocarbonyl, di(C
1
-C
6
alyl)aminothiocarbonyl, the alkyl groups being the same or different; C
1
-C
6
alkylamino, di(C
1
-C
6
alkyl)amino, the alkyl groups being the same or different; NO
2
, CN, SF
5
, thioamido, thiocyanatomethyl, trimethylsilyl; C
1
-C
4
alkylenedioxy or —CH═CH—CH═CH— each of which is unsubstituted or, depending on its substitution possibilities, mono- to tetra-substituted, the substituents of the C
1
-C
4
alkylenedioxy or —CH═CH—CH═CH— group being selected from the group consisting of C
1
-C
4
alkyl and halogen; a heterocyclyl, aryl-Q-C
1
-C
6
alkyl, aryl-Q—C
2
-C
6
alkenyl, heterocyclyl-Q—C
1
-C
6
alkyl or heterocyclyl-Q—C
2
-C
6
-alkenyl, or aryl-Q—, heterocycylyl-Q—, aryl-Q—C
1
-C
6
alkyl, aryl-Q—C
2
-C
6
alkenyl, heterocyclyl-Q—C
1
-C
6
-alkyl or heterocyclyl-Q—C
2
-C
6
alkenyl each of which is, depending on its substitution possibilities, mono- to penta-substituted in the aryl or heterocyclyl ring, the substituents being selected independently of one another from the group consisting of halogen, C
1
-C
6
alkyl, halo-C
1
-C
6
alkyl, C
3
-C
6
cycloalkyl, halo-C
3
-C
6
cycloalkyl, C
1
-C
6
alkoxy, halo-C
1
-C
6
alkoxy, CN, nitro and C
1
-C
6
alkoxycarbonyl; and, when n is greater than 1, the radicals R
5
are the same or different;
n is 0, 1, 2, 3 or, if either a or b is 0, 4;
Q is a direct bond, —CH(OH)—, —C(═O), —S—, —S(═O) or —S(═O)
2
;
R
9
is methyl, fluoromethyl or difluoromethyl; either
A is a direct bond, C
1
-C
10
alkylene, —C(═O)—, —C(═S)— or halo-C
1
-C
10
alkylene and
R
7
is a radical R
10
; or
A is C
1
-C
10
alkylene, —C(═O)—, —C(═S) or halo-C
1
-C
10
alkylene and
R
7
is —CN, OR
10
, N(R
10
)
2
, the radicals R
10
being the same or different, —SR
10
, —S(═O)R
10
or —S(═O)
2
R
10
R
10
is H, C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl or C
3
-C
6
cycloalkyl, or C
1
-C
6
alkyl, C
2
-C
8
-alkenyl, C
2
-C
8
alkynyl or C
3
-C
6
cycloalkyl each mono- or poly-substituted by substituents from the group consisting of halogen; —Si(C
1
-C
4
alkyl)
3
, the alkyl groups being the same or different; C
1
-C
6
alkoxycarbonyl or an aryl or heterocyclyl group that is unsubstituted or mono- or poly-substituted by substituents selected from the group consisting of halogen, C
1
-C
4
alkyl and halo-C
1
-C
4
alkyl; and
D is O, S, —S(═O) or S(═O);
G is C
1
-C
8
alkylene;
T—R
6
is R
6
; —C(═N—O—A
1
—R
77
)—R
6
; —SiR
14
(R
15
)—R
6
; —C(═O)—R
6
; C(R
16
)═C(R
17
)—R
6
; —C≡C—R
6
or —D—R
6
;
R
6
is C
1
-C
4
alkyl, aryl or heteroaryl; or aryl or heteroaryl each of which—depending on the substitution possibilities on the ring structure—is mono- to penta-substituted by substituents selected independently of one another from the group consisting of (R
5
)
s
; is, depending on the substitution possibilities on the ring, 0, 1, 2, 3, 4 or 5, the substituents R
5
being independent of one another when s is greater than 1;
A
1
and R
77
are as defined above for A and R
7
;
a is 0 or 1;
L is U—R
18
, P(O)
v
R
11
R
12
, P(S)
w
R
11
R
12
or N(aryl)R
13
, the aryl radical being either unsubstituted or mono- to penta-substituted by substituents selected independently of one another from the group consisting of R
5
;
v and ware 0 or 1;
U—R
18
is —C(═O)—C(═O)—R
18
; —C(OH)—C(OH)—R
18
; —C(═N—O—A
1
—R
7
)—R
18
;
p is from 0 to4;
R
11
and R
12
are each independently of the other C
1
-C
6
alkyl, halo-C
1
-C
6
alkyl, C
3
-C
6
cycloalkyl, halo-C
3
-C
6
cycloalkyl, C
1
-C
6
alkoxy, halo
1
-C
6
alkoxy, C
1
-C
6
alkylthio, halo-C
1
-C
6
alkylthio, aryl, heteroaryl, aryloxy, arylthio, heteroaryloxy or heteroarylthio; or aryl, heteroaryl, aryloxy, arylthio, heteroaryloxy or heteroarylthio each mono- to penta-substituted by R
5
, the substituents R
5
being independent of one another;
b is 0 or 1, but a and b are not simultaneously 0;
R
13
is hydrogen, C
1
-C
6
alkyl, halo-C
1
-C
6
alkyl, C
3
-C
6
cycloalkyl, halo-C
3
—C
6
-cycloalkyl, C
1
-C
6
alkylsulfinyl, halo-C
1
-C
6
alkylsulfinyl, C
1
-C
6
alkylsulfonyl, halo-C
1
-C
6
alkylsulfonyl, C
1
-C
6
alkoxy-C
1
-C
6
alkyl, halo-C
1
-C
6
alkoxy-C
1
-C
6
alkyl, C
1
-C
6
alkylthio-C
1
-C
6
alkyl, halo-C
1
-C
6
alkylthio-C
1
-C
6
alky, C
1
-C
6
alkylsulfinyl-C
1
-C
6
alkyl, halo-C
1
-C
6
alkylsulfinyl-C
1
-C
6
alkyl, C
1
-C
6
alkylsulfonyl-C
1
-C
6
alkyl, halo-C
1
-C
6
alkylsulfonyl-C
1
-C
6
alkyl, formyl, C
1
-C
6
alkylcarbonyl, C
1
-C
6
alkyl-C(═S)—, C
1
-C
6
alkylthio-C(═S)—, halo-C
1
-C
6
alkylcarbonyl, C
1
-C
6
alkoxycarbonyl, halo-C
1
-C
6
alkoxycarbonyl, C
1
-C
6
alkylaminocarbonyl, C
1
-C
4
-alkoxyiminomethyl, di(C
1
-C
6
alkyl)aminocarbonyl, the alkyl groups being the same or different; C
1
-C
6
alkylaminothiocarbonyl, di(C
1
-C
6
alkyl)aminothiocarbonyl, the alkyl groups being the same or different; C
1
-C
6
alkyldicarbonyl, halo-C
1
-C
6
alkyldicarbonyl, C
1
-C
6
alkoxydicarbonyl, halo-C
1
-C
6
alkoxydicarbonyl, C
1
-C
6
alkylaminodicarbonyl, di(C
1
-C
6
alkyl)aminodicarbonyl, the alkyl groups being the same or different; C
1
-C
6
alkylaminodithiocarbonyl, di(C
1
-C
6
alkyl)aminodithiocarbonyl, the alkyl groups being the same or different; aryl, arylsulfinyl, aryl-C
1
-C
6
alkylsulfinyl, arylsulfonyl, aryl-C
1
-C
6
alkyl-sufonyl, aryloxy-C
1
-C
6
alkyl, arylthio-C
1
-C
6
alkyl, aryl-C
1
-C
6
alkylsulfinyl-C
1
-C
6
alkyl, aryl-C
1
-C
6
alkylsulfonyl-C
1
-C
6
alkyl, arylcarbonyl, arylalkylcarbonyl, aryloxycarbonyl, arylalkoxycarbonyl, arylaminocarbonyl, aryloxyiminomethyl, di(aryl)aminocarbonyl, the aryl groups being the same or different; arylaminothiocarbonyl, di(aryl)aminothiocarbonyl, the aryl groups being the same or different; aryldicarbonyl, aryl-C
1
-C
6
alkyldicarbonyl, aryloxydicarbonyl, aryl-C
1
-C
6
alkoxydicarbonyl, arylaminodicarbonyl, di(aryl)aminodicarbonyl, the aryl groups being the same or different; arylaminodithiocarbonyl, di(arylaminodithiocarbonyl, the aryl groups being the same or different; and the aryl groups in the afore-mentioned substituents being unsubstituted or mono- to penta-substituted by substituents R
5
, the substituents R
5
being independent of one another; unsubstituted or substituted heteroaryl, unsubstituted or substituted heteroarylcarbonyl, unsubstituted or substituted heteroarylsulfinyl, or unsubstituted or substituted heteroarylsulfonyl;
R
14
and R
15
are each independently of the other C
1
-C
4

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