Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-07-12
2001-08-28
Ford, John M. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S269000, C514S272000, C514S274000, C514S275000, C544S299000, C544S301000, C544S302000, C544S303000, C544S309000, C544S311000, C544S312000, C544S314000, C544S315000, C544S316000, C544S317000, C544S318000, C544S319000, C544S321000, C544S322000, C544S323000, C544S326000, C544S327000, C544S329000, C544S330000, C544S332000, C544S335000
Reexamination Certificate
active
06281219
ABSTRACT:
BACKGROUND OF THE INVENTION
A class of pesticidal diaryl pyrimidine compounds is disclosed in U.S. Pat. No. 5,707,995. These compounds all contain 4,6-bis-aryl-pyrimidines wherein the aromatic groups are attached via two linking groups which are identical to one another. The present invention relates to a class of 4,6-bis-aryl-pyrimidines linked by different functional groups which has surprisingly been found to have acaricidal and insecticidal activity.
SUMMARY OF THE INVENTION
The present invention provides compounds of Formula I
wherein
R
1
is hydrogen, (C
1-6
)alkylthio, halo(C
1-6
)alkylthio (C
1-6
)alkylsulphinyl, halo(C
1-6
)alkylsulphinyl, (C
1-6
)alkylsulphonyl, halo(C
1-6
)alkylsulphonyl or NR
12
R
13
;
R
12
and R
13
are each independently hydrogen,(C
1-6
)alkyl, or halo(C
1-6
)alkyl;
R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, R
9
and R
11
are each independently selected from hydrogen, halogen, cyano, nitro, (C
1-6
)alkyl, halo(C
1-6
)alkyl, (C
1-6
)alkoxy, halo (C
1-6
)alkoxy, (C
1-6
)alkoxy(C
1-6
)alkyl, halo(C
1-6
)alkoxy(C
1-6
)alkyl, (C
1-6
)alkylthio, halo(C
1-6
)alkylthio, (C
1-6
)alkyl sulphinyl, halo(C
1-6
)alkylsulphinyl, (C
1-6
)alkylsulphonyl, halo(C
1-6
)alkylsulphonyl, amino, (C
1-6
)alkylamino, di(C
1-6
)alkylamino, halo(C
1-6
)alkylamino, (C
1-6
)alkylhaloalkyl (C
1-6
) amino, dihalo(C
1-6
)alkylamino, (C
1-6
)alkyloxy-carbonyl, halo(C
1-
6
)alkyloxycarbonyl, (C
2-6
)alkenyl, halo(C
2-6
)alkenyl, (C
2-6
)alkynyl, halo(C
2-6
)alkynyl;
R
10
is halogen, halo(C
1-6
)alkyl, halo(C
2-6
)alkenyl or halo(C
2-6
)alkynyl;
and X
1
and X
2
are independently selected from the group consisting of NR
14
, NR
15
, O, CH
2
, CR
18
R
19
, CO, C═NOR
20
;
wherein R
14
is (C
1-6
)alkyl;
R
15
is H, (C
1-6
)alkyl or CH(OR
16
)(OR
17
);
R
16
and R
17
are each independently (C
1-6
)alkyl;
R
18
and R
19
each independently selected from H, (C
1-6
)alkyl, (C
2-6
)alkenyl and (C
2-6
)alkynyl which are all optionally substituted by one or more halogens which are the same or different, or R
18
and R
19
may together form a carbocyclic ring which is optionally substituted by one or more halogens which are the same or different; R
20
is (C
1-6
)alkyl;
with the proviso that X
1
cannot be the same as X
2
.
Also provided are a process for the preparation of the formula I compound and a method for the control of acarina and insects therewith.
DETAILED DESCRIPTION OF THE INVENTION
Preferred compounds of the present invention include compounds of Formula I
wherein
R
1
is hydrogen, (C
1-6
)alkylthio, halo(C
1-6
)alkylthio (C
1-6
)alkylsulphinyl, halo(C
1-6
)alkylsulphinyl, (C
1-6
)alkylsulphonyl, halo(C
1-6
)alkylsulphonyl or NR
12
R
13
;
R
12
and R
13
are each independently hydrogen, (C
1-6
)alkyl, or halo(C
1-6
)alkyl;
R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, R
9
and R
11
are each independently selected from hydrogen, halogen, cyano, nitro, (C
1-6
)alkyl, halo(C
1-6
)alkyl, (C
1-6
)alkoxy, halo (C
1-6
)alkoxy, (C
1-6
)alkoxy(C
1-6
)alkyl, halo(C
1-6
)alkoxy(C
1-6
)alkyl, (C
1-6
)alkylthio, halo(C
1-6
)alkylthio, (C
1-6
)alkyl sulphinyl, halo(C
1-6
)alkylsulphinyl, (C
1-6
)alkylsulphonyl, halo(C
1-6
)alkylsulphonyl, amino, (C
1-6
)alkylamino, di(C
1-6
)alkylamino, halo(C
1-
6
)alkylamino, (C
1-6
)alkylhalo(C
1-6
)alkylamino, dihalo(C
1-6
)alkylamino, (C
1-6
)alkyloxycarbonyl, halo(C
1-6
)alkyloxycarbonyl, (C
2-6
)alkenyl, halo(C
2-6
)alkenyl, (C
2-6
)alkynyl, halo(C
2-6
)alkynyl;
R
10
is halogen, halo(C
1-6
)alkyl, halo(C
2-6
)alkenyl or halo(C
2-6
)alkynyl;
and a) one of X
1
and X
2
is NR
14
and the other is O or S,
wherein R
14
is (C
1-6
)alkyl
or b) one of X
1
and X
2
is NR
15
and the other is CH
2
,
wherein R
15
is H, (C
1-6
)alkyl or CH(OR
16
)(OR
17
) and R
16
and R
17
are each independently (C
1-6
)alkyl;
or c) one of X
1
and X
2
is CR
18
R
19
or CO and the other is O,
wherein R
18
and R
19
each independently selected from H, (C
1-6
)alkyl, (C
2-6
)alkenyl and (C
2-6
)alkynyl which are all optionally substituted by one or more halogens which are the same or different, or R
18
and R
19
may together form a carbocyclic ring which is optionally substituted by one or more halogens which are the same or different or d) one of X
1
and X
2
is C═NOR
20
and the other is CH
2
,
wherein R
20
is (C
1-6
)alkyl
with the proviso that the formula I compound is not 4-[m-(trifluoromethyl)benzyl]-6-(&agr;,&agr;,&agr;-trifluoro-N-methyl-m-toluidino)pyrimidine.
When used herein as a definition or part of a definition the term halogen or halo refers to fluorine, chlorine, bromine and iodine; preferred halogens are fluorine and chlorine; more preferred is fluorine.
When used herein as a definition or part of a definition the term alkyl is a straight or branched chain group such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, n-pentyl, 2-pentyl, 3-pentyl and n-hexyl. Preferred alkyl groups are methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl and n-pentyl; more preferred alkyl groups are methyl and ethyl.
When used herein as a definition or part of a definition the term alkenyl is a straight or branched chain group such as vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, pentenyls and hexenyls.
When used herein as a definition or part of a definition the term alkynyl is a straight or branched chain group such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl and 3-butynyl.
R
10
is preferably chlorine, halo(C
1-4
)alkyl or halovinyl; more preferably chlorine or a (C
1-4
)alkyl or vinyl group substituted by one or more fluorine or chlorine atoms; most preferably CF
3
or CF
2
CF
3
.
R
3
is preferably halogen, halo(C
1-6
)alkyl, halo(C
2-6
)alkenyl or halo(C
2-6
)alkynyl; more preferably R
3
is halo, halo(C
1-4
)alkyl or halovinyl; most preferably chlorine or a (C
1-4
)alkyl or vinyl group substituted by one or more fluorine or chlorine atoms; particular examples of R
3
are chlorine, CF
3
or CF
2
CF
3
.
R
4
and R
9
are each preferably selected from hydrogen, halogen, cyano, nitro, (C
1-6
)alkyl, halo(C
1-6
)alkyl, (C
1-6
)alkoxy, halo (C
1-6
)alkoxy, (C
1-6
)alkoxy(C
1-6
)alkyl, halo(C
1-6
)alkoxy(C
1-6
)alkyl, (C
1-6
)alkylthio, (C
2-6
)alkenyl, halo(C
2-6
)alkenyl, (C
2-6
)alkynyl, halo(C
2-6
)alkynyl; more preferably hydrogen or a halogen, most preferably fluorine or chlorine.
R
2
, R
5
, R
6
, R
7
, R
8
and R
11
are each preferably selected from hydrogen, halogen, cyano, nitro, (C
1-6
)alkyl, halo(C
1-6
)alkyl, (C
1-6
)alkoxy, halo (C
1-6
)alkoxy, (C
1-6
)alkoxy(C
1-6
)alkyl, halo(C
1-6
)alkoxy(C
1-6
)alkyl, (C
1-6
)alkylthio, (C
2-6
)alkenyl, halo(C
2-6
)alkenyl, (C
2-6
)alkynyl, halo(C
2-6
)alkynyl; more preferably each is hydrogen or a halogen, most preferably hydrogen.
R
12
and R
13
are each preferably selected from methyl, ethyl, propyl or butyl, more preferably they are both methyl. R
14
, R
15
, R
16
and R
17
are each preferably methyl, ethyl, propyl or butyl, more preferably methyl or ethyl. Preferred compounds being those in which R
16
and R
17
are identical.
R
18
and R
19
are preferably methyl, ethyl, propyl, butyl or together form a cyclopropyl, cyclobutyl or cyclopentyl ring. More preferably both R
12
and R
13
are methyl or they together form a cyclopropyl ring.
A preferred group of compounds are those wherein X
1
is NR
14
and X
2
is O. Preferred embodiments within this group are those wherein R
3
, R
4
and R
9
are independently selected from hydrogen, halo, halo(C
1-6
)alkyl, halo(C
2-6
)alkenyl or halo(C
2-6
)alkynyl. Preferred compounds within this group are those wherein R
10
is halo(C
1-6
)alkyl and R
9
is hydrogen or a halogen, particularly compounds wherein R
10
is CF
3
and R
9
is hydrogen, chlorine or fluorine. More preferred compounds within this group are those wherein R
4
is hydrogen or a halogen and R
3
is halo(C
1-6
)alkyl, particularly where R
4
is hydrogen, chlorine or fluorine and R
3
is CF
3
. Most preferred compounds within this group are those wherein R
3
and R
10
are CF
3
and R
4
and R
9
are fluorine or chlorine, preferably
Buckwalter Brian Lee
Chiarello John Francis
Cuccia Salvatore John
Fleming Linda Barbara
Wood William Wakefield
American Cyanamid Co.
Ford John M.
Maurer Barbara V.
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