Phthalic acid diamide, method for the production thereof and...

Details Phthalic acid diamide, method for the production thereof and... Phthalic acid diamide, method for the production thereof and...

2003-08-01

2004-12-28

Kumar, Shailendra (Department: 1621)

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

Organic compounds

Silicon containing

C514S063000, C514S770000

Reexamination Certificate

active

06835847

ABSTRACT:

The present invention relates to novel phthalamides, to a process for the preparation and to their use as pesticides.
It is already known that numerous phthalamides have insecticidal properties (cf. EP 0 919 542 A and EP 1 006 107 A). However, with respect to their compatibility with plants and efficacy, the known compounds are not always satisfactory. It has now been found that phthalamides which contain a silicon atom in the side chain have very good insecticidal and acaricidal properties and are tolerated well by plants.
This invention, accordingly, provides phthalamides of the formula (I)
in which
X and Y independently of one another represent hydrogen, halogen, cyano, nitro, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, cycloalkyl, halogenocycloalkyl, cycloalkyloxy, halogenocycloalkyloxy, —S(O)
d
-alkyl, —S(O)
d
-halogenoalkyl or represent in each case optionally substituted phenyl, phenoxy, heteroaryl or heteroaryloxy,
n represents 1, 2, 3 or 4,
m represents 1, 2, 3, 4 or 5,
R
1
, R
2
, R
3
and R
4
independently of one another represent hydrogen, alkyl, halogenoalkyl or cycloalkyl,
R
5
, R
6
and R
7
independently of one another represent alkyl or alkoxy,
A represents —S(O)
d
— or oxygen,
a represents 1, 2, 3 or 4, with the proviso that the repeat unit —CR
1
R
2
— may have identical or different meanings if a represents 2, 3 or 4,
b represents 0 or 1,
c represents 0, 1, 2, 3 or 4, with the proviso that the repeat unit —CR
3
R
4
— may have identical or different meanings if c represents 2, 3 or 4,
d represents 0, 1 or 2.
Depending on the nature and number of substituents, the compounds of the formula (I) may, if appropriate, be present as geometrical and/or optical isomers, regioisomers and/or configurational isomers or isomer mixtures thereof of varying compositions. What is claimed by the invention are both the pure isomers and the isomer mixtures.
Furthermore, it has been found that the novel compounds of the formula (I) obtained by reacting imides of the formula (II)
in which
X, Y, n and m have the meanings given above
with silylamines of the formula (III)
H
2
N—(CR
1
R
2
)
a
—A
b
—(CR
3
R
4
)
c
—Si(R
5
R
6
R
7
)  (III)
 in which
R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, A, a, b and c have the meanings given above,
if appropriate in the presence of a diluent.
Finally, it has been found that the compounds of the formula (I) according to the invention have very good insecticidal properties and can be used in both crop protection and in the protection of materials for controlling undesirable pests, such as insects and acarids. Surprisingly, the phthalamides according to the invention, which contain a silicon atom in the side chain, have very good insecticidal-and acaricidal activity and are at the same time tolerated well by plants.
The formula (I) provides a general definition of the phthalamides according to the invention.
X and Y independently of one another preferably represent hydrogen, halogen, cyano, nitro, C
1
-C
6
-alkyl, C
1
-C
6
-halogenoalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-halogenoalkoxy, C
3
-C
6
-cycloalkyl, C
3
-C
6
-halogenocycloalkyl, C
3
-C
6
-cycloalkyloxy, C
3
-C
6
-halogenocycloalkyloxy, —S(O)
d
—C
1
-C
6
-alkyl, —S(O)
d
—C
1
-C
6
-halogenoalkyl or represent phenyl, phenoxy, heteroaryl or heteroaryloxy, each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of halogen, C
1
-C
6
-alkyl and C
1
-C
6
-halogenoalkyl.
X and Y furthermore independently of one another preferably represent phenyl, phenoxy, heteroaryl or heteroaryloxy, each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of C
1
-C
6
-alkoxy, C
1
-C
6
-halogenoalkoxy, C
1
-C
6
-alkylthio and C
1
-C
6
-halogenoalkylthio.
n preferably represents 1, 2 or 3.
m preferably represents 1, 2, 3 or 4.
R
1
, R
2
, R
3
and R
4
independently of one another preferably represent hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-halogenoalkyl or C
3
-C
6
-cycloalkyl.
R
5
, R
6
and R
7
independently of one another preferably represent C
1
-C
6
-alkyl or C
1
-C
6
-alkoxy.
A preferably represents —S(O)
d
— or oxygen.
a preferably represents 1, 2, 3 or 4, with the proviso, that the repeat unit —CR
1
R
2
— may have identical or different meanings if a represents 2, 3 or 4.
b preferably represents 0 or 1.
c preferably represents 0, 1, 2, 3 or 4, with the proviso that the repeat unit —CR
3
R
4
— may have identical or different meanings if c represents 2, 3 or 4.
d preferably represents 0, 1 or 2.
X and Y independently of one another particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl having 1 to 9 fluorine, chlorine and/or bromine atoms, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenoalkoxy having 1 to 9 fluorine, chlorine and/or bromine atoms, C
3
-C
6
-cycloalkyl, —S(O)
d
—C
1
-C
4
-alkyl, —S(O)
d
—C
1
-C
4
-halogenoalkyl having 1 to 9 fluorine, chlorine and/or bromine atoms.
Y furthermore particularly preferably represents phenyl, phenoxy, 5- or 6-membered heteroaryl or heteroaryloxy having 1 to 4 heteroatoms including 0 to 4 nitrogen atoms, 0 to 2 nonadjacent oxygen atoms and/or 0 to 2 nonadjacent sulphur atoms (in particular furyl, furyloxy, thienyl, thienyloxy, pyrrolyl, pyrrolyloxy, tetrazolyl, pyridyl, pyridyloxy, pyrimidinyl, pyrimidinyloxy, pyridazinyl, pyridazinyloxy, pyrazinyl, pyrazinyloxy), each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, iodine, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl having 1 to 9 fluorine, chlorine and/or bromine atoms, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenoalkoxy having 1 to 9 fluorine, chlorine and/or bromine atoms, C
1
-C
4
-alkylthio, C
1
-C
4
-halogenoalkylthio having 1 to 9 fluorine, chlorine and/or bromine atoms.
n particularly preferably represents 1 or 2.
m particularly preferably represents 1, 2 or 3.
R
1
, R
2
, R
3
and R
4
independently of one another particularly preferably represents hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl having 1 to 9 fluorine, chlorine and/or bromine atoms or C
3
-C
6
-cycloalkyl.
R
5
, R
6
and R
7
independently of one another particularly preferably represents C
1
-C
3
-alkyl or C
1
-C
3
-alkoxy.
A particularly preferably represents —S(O)
d
— or oxygen.
a particularly preferably represents 1, 2 or 3, with the proviso that the repeat unit —CR
1
R
2
— may have identical or different meanings if a represents 2 or 3.
b particularly preferably represents 0 or 1.
c particularly preferably represents 0, 1, 2 or 3, with the proviso that the repeat unit —CR
3
R
4
— may have identical or different meanings if c represents 2 or 3.
d particularly preferably represents 0, 1 or 2.
X very particularly preferably represents chlorine, bromine, iodine.
Y very particularly preferably represents methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, pentafluoroethyl, n-heptafluoropropyl, isoheptafluoropropyl, trifluoromethoxy or —OCF
2
CF
2
H.
Y furthermore very particularly preferably represents phenoxy, pyridinyloxy or tetrazolyl, each of which is mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, —CF
3
, —CHF
2
, —CClF
2
, —CF
2
CHFCl, —CF
2
CH
2
F, —CF
2
CCl
3
, —CH
2
CF
3
, —CF
2
CHFCF
3
, —CH
2
CF
2
H, —CH
2
CF
2
CF
3
, —CF
2
CF
2
H, —CF
2
CHFCF
3
, —OCF
3
, —OCHF
2
, —OCF
2
CF
2
H, —SCF
3
, —SCHF
2
.
n very particularly preferably represents 1.
m very particularly preferably represents 2.
R
1
, R
2
, R
3
and R
4
independently of one another very particularly preferably represent hydrogen, methyl or ethyl.
R
5
, R
6
and R
7
independently of one another very particularly preferably represents methyl, ethyl, methoxy or ethoxy.
A very particularly preferably represents —S(O)
d
— or oxygen.
a very particularly preferably represents 1, 2 or 3, with the proviso that the repeat unit —CR
1
R

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