Pesticides

Details Pesticides Pesticides

1999-06-29

2002-07-16

Lambkin, Deborah C. (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

C514S599000, C514S620000, C514S513000, C560S035000, C564S074000, C564S165000, C558S230000

Reexamination Certificate

active

06420423

ABSTRACT:

The invention relates to compounds of the formula:
in which
(A) either
X is CH or N,
Y is OR
1
and
Z is O; or
X is N;
Y is NHR
8
and
Z is O, S or S(═O);
R
1
is C
1
-C
4
alkyl;
R
2
is H, C
1
-C
4
alkyl, halogeno-C
1
-C
4
alkyl, C
3
-C
6
cycloalkyl, C
1
-C
4
alkoxymethyl, C
1
-C
4
alkoxy, halogeno-C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, halogeno-C
1
-C
4
alkylthio or CN;
R
3
and R
4
independently of one another are H, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, OH, CN, NO
2
, a (C
1
-C
4
alkyl)
3
—Si group, where the alkyl groups can be identical or different, halogen, (C
1
-C
4
alkyl)S(═O)
m
, (halogeno-C
1
-C
4
alkyl)S(═O)
m
, halogeno-C
1
-C
4
alkyl or halogeno-C
1
-C
4
alkoxy;
R
8
is H or C
1
-C
4
alkyl;
R
9
is methyl, fluoromethyl or difluoromethyl;
m is 0, 1 or 2;
G is O or S; and
A is a direct bond, C
1
-C
10
alkylene, —C(═O)—, —C(═S)— or halogeno-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 halogeno-C
1
-C
10
alkylene and
R
7
is —CN, OR
10
, N(R
10
)
2
, where the radicals R
10
can be identical or different, or —S(═O)
p
R
10
;
R is an unsubstituted or mono- or polysubstituted C
1
-C
4
alkyl-, C
2
-C
4
alkenyl-, C
2
-C
4
alkynyl-, C
3
-C
6
cycloalkyl-, benzyl-, aryl or heteroaryl-group, where the substituents of the groups independently of one another are chosen from the group consisting of halogen, C
1
-C
6
alkyl, halogeno-C
1
-C
6
alkyl, C
3
-C
6
cycloalkyl, halogeno-C
3
-C
6
cycloalkyl, C
1
-C
6
alkoxy, halogeno-C
1
-C
6
alkoxy, C
1
-C
6
alkylthio, halogeno-C
1
-C
6
alkylthio, phenoxy, CN and nitro, or a phenyl radical which is monosubstituted on two adjacent C atoms by an unsubstituted or mono- to tetrasubstituted C
1
-C
4
alkylenedioxy group, where the substituents are selected from the group consisting of C
1
-C
4
alkyl and halogen; or CH
2
Si(C
1
-C
4
alkyl)
3
, where the alkyl groups can be identical or different; and
R
5
is C
1
-C
6
alkyl, halogeno-C
1
-C
6
alkyl, C
3
-C
6
cycloalkyl, halogeno-C
3
-C
6
cycloalkyl, C
1
-C
6
alkoxy, halogeno-C
1
-C
6
alkoxy, C
1
-C
6
alkylthio, halogeno-C
1
-C
6
alkylthio, C
1
-C
6
alkylsulfinyl, halogeno-C
1
-C
6
alkylsulfinyl, C
1
-C
6
alkylsulfonyl, halogeno-C
1
-C
6
alkylsulfonyl, C
1
-C
6
alkylsulfonyloxy, halogeno-C
1
-C
6
alkylsulfonyloxy, C
1
-C
6
alkoxy-C
1
-C
6
alkyl, halogeno-C
1
-C
6
alkoxy-C
1
-C
6
alkyl, C
1
-C
6
alkylthio-C
1
-C
6
alkyl, halogeno-C
1
-C
6
alkylthio-C
1
-C
6
alkyl, C
1
-C
6
alkylsulfinyl-C
1
-C
6
alkyl, halogeno-C
1
-C
6
alkylsulfinyl-C
1
-C
6
alkyl, C
1
-C
6
alkylsulfonyl-C
1
-C
6
alkyl, halogeno-C
1
-C
6
alkylsulfonyl-C
1
-C
6
alkyl, C
1
-C
6
alkylcarbonyl, halogeno-C
1
-C
6
alkylcarbonyl, C
1
-C
6
alkoxycarbonyl, halogeno-C
1
-C
6
alkoxycarbonyl, C
1
-C
6
alkylaminocarbonyl, C
1
-C
4
alkoxyiminomethyl, di(C
1
-C
6
alkyl)aminocarbonyl, where the alkyl groups can be identical or different; C
1
-C
6
alkylaminothiocarbonyl, di(C
1
-C
6
alkyl)aminothiocarbonyl, where the alkyl groups can be identical or different; C
1
-C
6
alkylamino, di(C
1
-C
6
alkyl)amino, where the alkyl groups can be identical or different; halogen, NO
2
, CN, SF
5
, thioamido, thiocyanatomethyl, trimethylsilyl; an unsubstituted or mono- to tetrasubstituted C
1
-C
4
alkylenedioxy group, where the substituents are chosen from the group consisting of C
1
-C
4
alkyl and halogen; aryl-Q-C
1
-C
6
alkyl, aryl-Q-C
2
-C
6
alkenyl, heterocyclyl-Q-C
1
-C
6
alkyl, heterocyclyl-Q-C
2
-C
6
alkenyl, or 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 which are mono- to pentasubstituted in the aryl or heterocyclyl ring, depending on the possibility of substitution, where the substituents independently of one another are chosen from the group consisting of halogen, C
1
-C
6
alkyl, halogeno-C
1
-C
6
alkyl, C
3
-C
6
cycloalkyl, halogeno-C
3
-C
6
cycloalkyl, C
1
-C
6
alkoxy, halogeno-C
1
-C
6
alkoxy, CN, nitro, OC(═O)-C
1
-C
6
alkyl, OH, NH
2
and C
1
-C
6
alkoxycarbonyl;
where, if q is greater than 1, the radicals R
5
can be identical or different;
Q is a direct bond, —CH(OH)—, —C(═O)— or —S(═O)
v
—;
v is 0, 1 or 2;
R
10
is H, C
1
-C
6
alkyl, C
2
-C
8
alkenyl, C
2
-C
8
alkynyl, C
3
-C
6
cycloalkyl; or C
1
-C
6
alkenyl, C
2
-C
8
alkynyl or C
3
-C
6
cycloalkyl-, which are mono- or polysubstituted by substituents from the group consisting of halogen; —Si(C
1
-C
4
alkyl)
3
, where the alkyl groups can be identical or different; C
1
-C
6
alkoxycarbonyl, or an aryl or heterocyclyl group which are unsubstituted or mono- or polysubstituted by substituents from the group consisting of halogen, C
1
-C
4
alkyl and halogeno-C
1
-C
4
alkyl, and
p is 0, 1 or 2; and
(B) either
(I) n is 1 or 2 and q is 1, 2, 3 or, when n 1 is, 4; and A, G, X, Y, Z, R, R
2
, R
3
, R
4
, R
5
, R
7
and R
9
are as defined above under (A); or
(II) n is 0;
q is 2,3,4 or 5; and
A, X, Y, Z, R
2
, R
3
, R
4
, R
5
, R
7
and R
9
are as defined above under (A); and the radicals R
5
can be identical or different; with the proviso that if q is 2, (R
5
)
2
is not dichloro or dimethyl, and with the further proviso that R
2
is not CH
3
if AR
7
is CH
3
and (R
5
)
2
is 3-fluoro, 5-CF
3
or, together, 3,4-methylenedioxy and R
3
R
4
are H ; or
(III) n is 0;
q is 1;
A, X, Y, Z, R
2
, R
3
, R
4
, R
7
and R
9
are as defined above under (A); and
R
5
is tert-butyl, C
5
-C
6
alkyl, halogeno-C
1
-C
6
alkyl, with the exception of CF
3
; C
3
-C
6
cycloalkyl, halogeno-C
3
-C
6
cycloalkyl, C
5
-C
6
alkoxy, halogeno-C
3
-C
6
alkoxy, C
2
-C
6
alkylthio, halogeno-C
1
-C
6
alkylthio, C
1
-C
6
alkylsulfinyl, halogeno-C
1
-C
6
alkylsulfinyl, C
2
-C
6
alkylsulfonyl, halogeno-C
1
-C
6
alkylsulfonyl, C
1
-C
6
alkylsulfonyloxy, halogeno-C
1
-C
6
alkylsulfonyloxy, C
1
-C
6
alkoxy-C
1
-C
6
alkyl, halogeno-C
1
-C
6
alkoxy-C
1
-C
6
alkyl, C
1
-C
6
alkylthio-C
1
-C
6
alkyl, halogeno-C
1
-C
6
alkylthio-C
1
-C
6
alkyl, C
1
-C
6
alkylsulfinyl-C
1
-C
6
alkyl, halogeno-C
1
-C
6
alkylsulfinyl-C
1
-C
6
alkyl, C
1
-C
6
alkylsulfonyl-C
1
-C
6
alkyl, halogeno-C
1
-C
6
alkylsulfonyl-C
1
-C
6
alkyl, C
1
-C
6
alkylcarbonyl, halogeno-C
1
-C
6
alkylcarbonyl, C
2
-C
6
alkoxycarbonyl, halogeno-C
1
-C
6
alkoxycarbonyl, C
2
-C
6
alkylaminocarbonyl, C
1
-C
4
alkoxyiminomethyl, di(C
2
-C
6
alkyl)aminocarbonyl, where the alkyl groups can be identical or different; C
1
-C
6
alkylaminothio-carbonyl, di(C
1
-C
6
alkyl)aminothiocarbonyl, where the alkyl groups can be identical or different; C
2
-C
6
alkylamino, di(C
2
-C
6
alkyl)amino, where the alkyl groups can be identical or different; SF
5
, thiocyanatomethyl, trimethylsilyl, aryl-Q-C
1
-C
6
alkyl, aryl-Q-C
2
-C
6
alkenyl, heterocyclyl-Q-C
1
-C
6
alkyl, heterocyclyl-Q-C
2
-C
6
alkenyl; or 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 which are mono- to pentasubstituted in the aryl or heterocyclyl ring, depending on the possibility of substitution, where the substituents independently of one another are chosen from the group consisting of halogen, C
1
-C
6
alkyl, halogeno-C
1
-C
6
alkyl, C
3
-C
6
cycloalkyl, halogeno-C
3
-C
6
cycloalkyl, C
1
-C
6
alkoxy, halogeno-C
1
-C
6
alkoxy, CN, nitro and C
1
-C
6
alkoxycarbonyl;
Q is a direct bond, —CH(OH)—, —C(═O)— or —S(═O)
v
—;
v is 0, 1 or 2; or
(IV) n is 1 and
q is 0;
A, X, Y, Z, R
2
, R
3
, R
4
, R
7
and R
9
are as defined above under (A);
G is O; and
R is n-propyl, n-butyl, sec-butyl, isobutyl, C
3
-C
6
cycloalkyl, C
3
-C
6
cycloalkyl-C
1
-C
4
alkyl, halogeno-C
4
-C
6
cycloalkyl-C
1
-C
4
alkyl, C
1
-C
4
alkylenyl-C
3
-C
6
cycloalkyl, C
1
-C
4
alkylenyl-halogeno-C
3
-C
6
cycloalkyl, CH
2
Si(C
1
-C
4
alkyl)
3
, where the alkyl groups can be identical or different; a substituted aryl or benzyl, where the substituents of the aryl or benzyl independently of one another are chosen from the group consisting of C
1
-C
6
alkyl, halogeno-C
1
-C
6
alkyl, C
3
-C
6
cycloalkyl, halogeno-C
3
-C
6
-cycloalkyl, C
1
-C
6
alkoxy, halogeno-C
1
-C
6
alkoxy, C
1
-C
6
alkylthio, halogeno-C
1
-C
6
alkylthio, phenoxy,

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