Pesticidal triazine-derivatives

Details Pesticidal triazine-derivatives Pesticidal triazine-derivatives

2001-11-05

2004-04-20

Ford, John M. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C544S182000

Reexamination Certificate

active

06723720

ABSTRACT:

The present invention relates to a compound of formula
wherein
R
1
is unsubstituted or mono- to penta-substituted aryl or heteroaryl, the substituents of the aryl and heteroaryl rings being selected from the group consisting of
OH, halogen, CN, NO
2
, C
1
-C
6
alkyl, C
3
-C
8
cycloalkyl, optionally substituted C
3
-C
8
cycloalkenyl, C
1
-C
6
alkyl-C
3
-C
8
cycloalkyl, C
3
-C
8
cycloalkyl-C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
8
halocycloalkyl, C
1
-C
6
alkoxy, C
3
-C
8
cycloalkoxy, C
1
-C
6
haloalkoxy, C
3
-C
8
halocycloalkoxy, C
1
-C
6
alkylthio, C
3
-C
8
cycloalkylthio, C
1
-C
6
haloalkylthio, C
3
-C
8
halocycloalkylthio, C
1
-C
6
alkylsulfinyl, C
3
-C
8
cycloalkylsulfinyl, C
1
-C
6
haloalkylsulfinyl, C
3
-C
8
halocycloalkylsulfinyl, C
1
-C
6
alkylsulfonyl, C
3
-C
8
cycloalkylsulfonyl, C
1
-C
6
haloalkylsulfonyl, C
3
-C
8
halocycloalkylsulfonyl, optionally substituted C
2
-C
8
alkenyl, optionally substituted C
2
-C
8
alkynyl, C
1
-C
6
alkylcarbonyl, C
1
-C
6
alkyl-C(═NOR
6
), —P(═O)(OC
1
-C
6
alkyl)
2
, R7,
unsubstituted or mono- to penta-substituted phenyl, unsubstituted or mono- to penta-substituted heteroaryl; wherein the substituents of the said phenyl and heteroaryl radicals are selected from the group consisting of OH, halogen, CN, NO
2
, C
1
-C
6
alkyl, optionally substituted C
2
-C
8
alkenyl, optionally substituted C
2
-C
8
alkynyl, C
3
-C
8
cycloalkyl, optionally substituted C
3
-C
8
cycloalkenyl, C
1
-C
6
haloalkyl, C
3
-C
8
halocycloalkyl, C
1
-C
6
alkoxy, C
3
-C
8
cycloalkoxy, C
1
-C
6
haloalkoxy, C
3
-C
8
halocycloalkoxy, C
1
-C
6
alkylthio, C
3
-C
8
cycloalkylthio, C
1
-C
6
haloalkylthio, C
3
-C
8
halocycloalkylthio, C
1
-C
6
alkylsulfinyl, C
3
-C
8
cycloalkylsulfinyl, C
1
-C
6
haloalkylsulfinyl, C
3
-C
8
halocycloalkylsulfinyl, C
1
-C
6
alkylsulfonyl, C
3
-C
8
cycloalkylsulfonyl, C
1
-C
6
haloalkylsulfonyl, C
3
-C
8
halocycloalkylsulfonyl, C
2
-C
8
alkenyl, which is unsubstituted or substituted, C
2
-C
8
alkynyl, which is unsubstituted or substituted, C
1
-C
6
alkylcarbonyl, —CH(═NOR
6
), —C(C
1
-C
6
alkyl)(═NOR
6
), C
1
-C
6
alkyl-C(═NOR
6
), —CHO, —C(═O)—C
1
-C
6
alkyl and R
7
;
unsubstituted or mono- to penta-substituted phenoxy;
unsubstituted or mono- to penta-substituted phenylthio;
unsubstituted or mono- to penta-substituted phenylamino; and
unsubstituted or mono- to penta-substituted phenyl-(C
1
-C
6
alkyl)-amino;
the substituents of the phenoxy, phenylthio, phenylamino and phenyl-(C
1
-C
6
alkyl)-amino groups being selected from the group consisting of halogen, CN, NO
2
, C
1
-C
6
alkyl, C
3
-C
8
-cycloalkyl, C
1
-C
6
haloalkyl, C
3
-C
8
halocycloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
3
-C
8
cycloalkoxy, C
1
-C
6
alkylthio, C
1
-C
6
alkylsulfinyl, C
1
-C
6
haloalkylsulfinyl, C
1
-C
6
alkylsulfonyl, C
1
-C
6
haloalkylsulfonyl, C
3
-C
8
cycloalkylthio, C
1
-C
6
haloalkylthio and C
3
-C
8
halocycloalkylthio;
R
2
is H, OH, halogen, CN, NO
2
, optionally substituted C
1
-C
6
alkyl, C
1
-C
6
alkoxy, C
1
-C
6
alkoxy-C
1
-C
6
alkyl, C
1
-C
6
alkylthio, C
1
-C
6
alkylthio-C
1
-C
6
alkyl, C
3
-C
8
cycloalkyl, C
1
-C
6
haloalkyl, C
3
-C
8
halocycloalkyl, —NH—C
1
-C
6
-alkyl, SH or CH
2
—NO
2
;
A is a single bond, C
1
-C
12
alkylene, O, O(C
1
-C
12
alkylene), S(O)
n
, S(O)
n
(C
1
-C
12
alkylene), C
2
-C
8
alkenylene, C
2
-C
8
alkynylene; NR
3
or NR
3
(C
1
-C
12
alkylene);
R
3
is H, C
1
-C
6
alkyl, C
3
-C
8
cycloalkyl, C
1
-C
6
haloalkyl, C
2
-C
8
alkenyl, C
2
-C
8
alkynyl, aryl-C
1
-C
6
alkyl, (CH
2
)
p
C(O)R
4
or C
1
-C
6
alkoxy-C
2
-C
6
alkyl;
R
4
is H, C
1
-C
6
alkyl, C
3
-C
8
cycloalkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, N(R
5
)
2
or C
1
-C
6
alkoxy-C
2
-C
6
alkyl;
R
5
is H, C
1
-C
6
alkyl, C
3
-C
8
cycloalkyl, C
1
-C
6
haloalkyl or aryl-C
1
-C
6
alkyl;
R
6
is H, C
1
-C
6
alkyl, C
3
-C
8
cycloalkyl or —C(═O)—R
5
;
R
7
is
R
8
and R
9
are each independently of the other H or C
1
-C
6
alkyl;
X
1
is R
10
;
X
2
and X
3
are each independently of the other H or R
10
;
R
10
is halogen, CN, NO
2
, C
1
-C
6
alkyl, C
3
-C
8
cycloalkyl, C
1
-C
6
haloalkyl, C
3
-C
8
halocycloalkyl, C
1
-C
6
alkoxy, C
3
-C
8
cycloalkoxy, C
1
-C
6
haloalkoxy, C
3
-C
8
halocycloalkoxy, C
1
-C
6
alkylthio, C
3
-C
8
cycloalkylthio, C
1
-C
6
haloalkylthio or C
3
-C
8
halocycloalkylthio;
m is 1, 2, 3 or 4;
n is 0, 1 or 2; and
W is O or S;
with the proviso that the radical A—R
1
and the phenyl group substituted by X
1
, X
2
and X
3
are not in the vicinal position relative to one another on the triazine ring,
with the further proviso, that X
1
is not CH
3
, Cl or F, when X
2
and X
3
are H, A is a single bond, R
1
is phenyl, 2-fluorophenyl, p-fluorophenyl or 3-chlorophenyl and R
2
is H, Cl or NHC
2
—H
5
;
and with the exception of 3,6-di-(2-chlorophenyl)-5-hydroxy-1,2,4-triazine and
with the exception of 3-(2-methylphenyl)-6-(4-methylphenyl)-5-trifluoromethyl-1,2,4-triazine;
and to the physiologically tolerable and agrochemically acceptable addition compounds thereof, and where appropriate to E/Z isomers, to mixtures of E/Z isomers and/or to tautomers, in each case in free form or in salt form;
to a process for the preparation of those compounds and to their use, to pesticidal compositions in which the active ingredient is selected from those compounds, in each case in free form or in agrochemically acceptable salt form, and to a process for the manufacture of those compositions and to their use.
Preferred are compounds of the formula (I), wherein
R
1
is unsubstituted or mono- to penta-substituted aryl or heteroaryl, wherein the substituents are selected from the group consisting of OH, Halogen, CN, NO
2
, C
1
-C
6
-Alkyl, C
3
-C
8
-Cycloalkyl, C
1
-C
6
-Alkyl-C
3
-C
8
-cycloalkyl, C
3
-C
8
-Cycloalkyl-C
1
-C
6
-alkyl, C
1
-C
6
-Haloalkyl, C
3
-C
8
-Halocycloalkyl, C
1
-C
6
-Alkoxy, C
3
-C
8
-Cycloalkoxy, C
1
-C
6
-Haloalkoxy, C
3
-C
8
-Halocycloalkoxy, C
1
-C
6
-Alkylthio, C
3
-C
8
-Cycloalkylthio, C
1
-C
6
-Haloalkylthio, C
3
-C
8
-Halocycloalkylthio, C
1
-C
6
-Alkylsulfinyl, C
3
-C
8
-Cycloalkylsulfinyl, C
1
-C
6
-Haloalkylsulfinyl, C
3
-C
8
-Halocycloalkylsulfinyl, C
1
-C
6
-Alkylsulfonyl, C
3
-C
8
-Cycloalkylsulfonyl, C
1
-C
6
-Haloalkylsulfonyl, C
3
-C
8
-Halocycloalkylsulfonyl, C
1
-C
8
-Alkenyl, C
2
-C
8
-Alkinyl, C
1
-C
6
-Alkylcarbonyl, C
1
-C
6
-Alkyl-C(═NOR
6
), R
7
, is unsubstituted or mono- to penta-substituted phenyl, wherein the substituents are selected from the group consisting of OH, Halogen, CN, NO
2
, C
1
-C
6
-Alkyl, C
3
-C
8
-Cycloalkyl, C
1
-C
6
-Haloalkyl, C
3
-C
8
-Halocycloalkyl, C
1
-C
6
-Alkoxy, C
3
-C
8
-Cycloalkoxy, C
1
-C
6
-Haloalkoxy, C
3
-C
8
-Halocycloalkoxy, C
1
-C
6
-Alkylthio, C
3
-C
8
-Cycloalkylthio, C
1
-C
6
-Haloalkylthio, C
3
-C
8
-Halocycloalkylthio, C
1
-C
6
-Alkylsulfinyl, C
3
-C
8
-Cycloalkylsulfinyl, C
1
-C
6
-Haloalkylsulfinyl, C
3
-C
8
-Halocycloalkylsulfinyl, C
1
-C
6
-Alkylsulfonyl, C
3
-C
8
-Cycloalkylsulfonyl, C
1
-C
6
-Haloalkylsulfonyl, C
3
-C
8
-Halocycloalkylsulfonyl, C
2
-C
8
-Alkenyl, C
2
-C
8
-Alkinyl, C
1
-C
6
-Alkylcarbonyl, C
1
-C
6
-Alkyl-C(═NOR
6
) and R
7
; is unsubstituted or mono- to penta-substituted phenoxy, is unsubstituted or mono- to penta-substituted phenylthio, is unsubstituted or mono- to penta-substituted phenylamino and is unsubstituted or mono- to penta-substituted phenyl-(C
1
-C
6
-alkyl)-amino, wherein the substituents are selected from the group consisting of Halogen, CN, NO
2
, C
1
-C
6
-Alkyl, C
3
-C
8
-Cycloalkyl, C
1
-C
6
-Haloalkyl, C
3
-C
8
-Halocycloalkyl, C
1
-C
6
-Alkoxy, C
3
-C
8
-Cycloalkoxy, C
1
-C
6
-Alkylthio, C
3
-C
8
-Cycloalkylthio, C
1
-C
6
-Haloalkylthio and C
3
-C
8
-Halocycloalkylthio;
R
2
is H, Halogen, CN, NO
2
, C
1
-C
6
-Alkyl, C
3
-C
8
-Cycloalkyl, C
1
-C
6
-Haloalkyl or C
3
-C
8
-Halocycloalkyl;
A is (CR
11
R
12
)
p
, O(CR
11
R
12
)
p
, S(O)
n
(CR
11
R
12
)
p
, unsubstituted or substituted C
2
-C
8
-Alkenylen, unsubstituted or substituted C
2
-C
8
-Alkinylen, wherein the substituents are selected from the group consisting of R
1
, and R
12
; or NR
3
(CH
2
)
p
;
R
3
is H, C
1
-C
6
-Alkyl, C
3
-C
8
-Cyc

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