Pesticidal pyrimidine-derivatives

Details Pesticidal pyrimidine-derivatives Pesticidal pyrimidine-derivatives

2001-11-05

2004-02-03

Ford, John M. (Department: 1624)

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

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

C544S334000, C544S335000, C544S242000, C544S326000, C544S327000

Reexamination Certificate

active

06686469

ABSTRACT:

The present invention relates to new pyrimidine derivatives of formula
wherein
R
1
is unsubstituted or mono- to penta-substituted aryl, whereby the substituents are selected from the group consisting of OH, Halogen, CN, C
1
-C
6
-alkyl, optionally substituted 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
-alkinyl, C
1
-C
6
-alkylcarbonyl, —C(═NOR
6
)—C
1
-C
6
-Alkyl; R
7
; unsubstituted or mono- to penta-substituted phenyl; unsubstituted or mono- to penta-substituted heteroaryl, whereby the substituents are respectively 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
3
-C
8
-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(═NOR
6
)—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 —N(phenyl)(C
1
-C
6
-alkyl), whereby the substituents are respectively 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
cycloalkythio, C
1
-C
6
-haloalkylthio and C
3
-C
8
-halocycloalkylthio;
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
-alkinylene; 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
-alkinyl, aryl-C
1
-C
6
-alkyl, (CH
2
)
p
C(O)R
4
or C
1
-C
6
-alkoxy-C
1
-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
1
-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 or C
3
-C
8
-cycloalkyl;
R
7
is
R
8
and R
9
independently of one another, are H or C
1
-C
6
-alkyl;
X
1
and X
2
, independently of one another, are R
10
;
X
3
is 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;
R
21
and R
22
, independently of one another, are H, halogen, CN, NO
2
, OH, SH, 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, haloC
3
-C
8
-cycloalkyl, C
1
-C
6
-alkoxy, C
3
-C
8
-cycloalkoxy, C
1
-C
6
-haloalkoxy, haloC
3
-C
8
-cycloalkylthio, C
1
-C
6
-alkylthio, C
3
-C
8
-cycloalkylthio, C
1
-C
6
-haloalkylthio, haloC
3
-C
8
-cycloalkylthio, C
1
-C
6
-alkylsulfinyl, C
3
-C
8
-cycloalkylsulfinyl, haloC
1
-C
6
-alkylsulfinyl, C
3
-C
8
-halocycloalkylsulfinyl, C
1
-C
6
-alkylsulfonyl, C
3
-C
8
-cycloalkylsulfonyl, C
1
-C
6
-haloalkylsulfonyl, haloC
3
-C
8
-cycloalkylsufonyl, N(R
23
)R
24
, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkoxy, C
1
-C
6
-alkoxy-C
1
-C
6
-alkylthio, C
1
-C
6
-alkoxy-C
1
-C
6
-alkylamino, C
2
-C
8
-alkenyloxy or C
2
-C
8
-alkinyloxy;
R
23
and R
24
, independently of one another, are H, 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 or C
3
-C
8
-halocycloalkyl;
m is 1, 2, 3 or 4;
n is 0, 1 or 2; and
Y is O or S;
as well as the physiologically acceptable addition compounds, and where appropriate to E/Z-isomers, to mixtures of E/Z isomers and/or to tautomers, in each case in the free form or in agrochemically employable salt form; a method of producing these compounds and the usage of these compounds, pesticide compositions whose active ingredient is chosen from these compounds, and a method of producing and using these compositions.
Preferred is a compound of the formula (I), wherein
R
1
is unsubstituted or mono- to penta-substituted aryl, wherein the substituents are selected from the group consisting of OH, Halogen, CN, 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
8
-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(═NOR
6
)—C
1
-C
6
-Alkyl, R
7
; 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
-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
2
-C
8
-Alkenyl, C
2
-C
8
-Alkinyl, C
1
-C
6
-Alkylcarbonyl, —C(═NOR
6
)—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 —N(phenyl)(C
1
-C
6
-alkyl), 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
21
and R
22
independently of one another 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
11
and R
12
; or NR
3
(CH
2
)
p
;
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
-Alkinyl, 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
-

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