Phthalamide derivatives

1. A phthalamide derivative of formula (I)

wherein

R 1 represents alkyl that is optionally halogen-substituted,

R 2 represents alkyl that is optionally substituted or cycloalkyl that is optionally substituted,

R 3 represents hydrogen, halogen, or alkyl that is optionally halogen-substituted,

R 4 represents hydrogen, halogen-substituted alkyl, halogen-substituted alkoxy, halogen-substituted phenyl, or halogen-substituted phenoxy, and

R 5 represents hydrogen, halogen, or alkyl that is optionally halogen-substituted.

2. A compound according to claim 1 wherein

R 1 represents C 1-6 alkyl that is optionally fluoro-substituted, chloro-substituted, or bromo-substituted,

R 2 represents C 1-6 alkyl that is optionally fluoro-substituted, chloro-substituted, bromo-substituted, C 1-4 alkoxy-substituted, C 1-4 alkylthio-substituted, C 1-4 alkylsulfinyl-substituted, or C 1-4 alkylsulfonyl-substituted; or represents C 3-6 cycloalkyl that is optionally halogen-substituted or C 1-4 alkyl-substituted,

R 3 represents hydrogen or halogen; or represents C 1-6 alkyl that is optionally fluoro-substituted, chloro-substituted, or bromo-substituted,

R 4 represents hydrogen, halogen-substituted C 1-6 alkyl, halogen-substituted C 1-6 alkoxy, halogen-substituted phenyl, or halogen-substituted phenoxy, and

R 5 represents hydrogen or halogen; or represents C 1-6 alkyl that is optionally fluoro-substituted, chloro-substituted, or bromo-substituted.

3. A compound according to claim 1 wherein

R 1 represents methyl, ethyl, propyl, or trifluoromethyl,

R 2 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, sec-hexyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, methylthiopropyl, ethylthiopropyl, methylthiobutyl, ethylthiobutyl, methylthiopentyl, ethylthiopentyl, methylsulfinylmethyl, ethylsulfinylmethyl, methylsulfinylethyl, ethylsulfinylethyl, methylsulfinylpropyl, ethylsulfinylpropyl, methylsulfinylbutyl, ethylsulfinylbutyl, methylsulfinylpentyl, ethylsulfinylpentyl, methylsulfonylmethyl, ethylsulfonylmethyl, methylsulfonylethyl, ethylsulfonylethyl, methylsulfonylpropyl, ethylsulfonylpropyl, methylsulfonylbutyl, ethylsulfonylbutyl, methylsulfonylpentyl, or ethylsulfonylpentyl; or represents cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl, each of which is optionally substituted with fluoro, chloro, bromo, methyl, or ethyl,

R 3 represents hydrogen, fluoro, chloro, bromo, methyl, ethyl, or trifluoromethyl,

R 4 represents fluoro, chloro, or bromo; or represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, or isopropoxy, each of which is optionally substituted with one or more fluoro, perfluoro-substituted, or substituted with one or more fluoro and 1 or 2 chloro, and

R 5 represents hydrogen, fluoro, chloro, or bromo; or represents methyl or ethyl, each of which is optionally fluoro-substituted or chloro-substituted.

4. A compound according to claim 1 wherein

R 1 represents methyl or ethyl,

R2 represents isopropyl, tert-butyl, 1-methyl-2-(methylthio)ethyl, 1,1-dimethyl-2-(methylthio)ethyl, 1-methyl-2-(methylsulfinyl)ethyl, 1,1-d imethyl-2-(methylsulfinyl)ethyl, 1-methyl-2-(methylsulfonyl)ethyl, or 1,1-d imethyl-2-(methylsulfonyl)ethyl,

R 3 represents methyl,

R 4 represents perfluoroisopropyl, and

R 5 represents hydrogen.

5. A process for the preparation of a compounds of formula (I) according to claim 1 comprising

(a) reacting a compound of formula (II)

wherein R 1 , R 3 , R 4 , and R 5 have the same definitions as for formula (I) of claim 1 ,

with a compound of formula (III)

H 2 N—R 2   (III)

wherein R 2 has the same definition as for formula (I) in claim 1 , in the presence of inert solvents and optionally in the presence of a base,

or

(b) reacting a compound of formula (IV)

wherein R 1 and R 2 have the same definitions as for formula (I) in claim 1 ,

with a compound of formula (V)

wherein R 3 , R 4 , and R 5 have the same definitions as for formula (I) in claim 1 ,

in the presence of inert solvents and optionally in the presence of an acid catalyst,

or

(c) reacting a compound of formula (VI)

wherein R 1 , R 3 , R 4 , and R 5 have the same definitions as for formula (I) in claim 1 ,

with a compound of formula (III),

H 2 N—R 2   (III)

wherein R 2 has the same definition as for formula (I) in claim 1 , in the presence of inert solvents and optionally in the presence of a acid catalyst,

or

(d) for compounds of formula (I) in which R 2 represents alkylsulfinylalkyl or alkylsulfonylalkyl, reacting a compound of formula (Id)

wherein

R 2d represents alkyithioalkyl, and

R 1 , R 3 , R 4 , and R 5 have the same definitions as for formula (I) in claim 1 , with an oxidizing agent in the presence of inert solvents.

6. An insecticidal composition containing one or more phthalamide derivatives of formula (I) according to claim 1 .

7. A process for combating insects comprising allowing an effective amount of one or more phthalamide derivatives of formula (I) according to claim 1 to act on the insects and/or their habitat.

8. A process for the preparation of insecticidal compositions comprising mixing one or more phthalamide derivatives of formula (I) according to claim 1 with one or more extenders and/or surface active agents.