Insecticide and method of controlling insects

An insecticide comprising the compound of formula I

• 41
• R1 is selected from the group consisting of:
• the group OR5 wherein R5 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, cycloalkyl, substituted cycloalkyl, heterocyclic and substituted heterocyclic;
• the group —NR6OH wherein R6 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, carbocyclic and substituted carbocyclic;
• the group NR7R8 wherein R7 and R8 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl and carbocyclic;
• and
• the group wherein R1 is linked to R2 to form a diradical bridging group;
• R2 and R3 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, carbocyclic, substituted carbocyclic, aryl, substituted aryl, acyl and substituted acyl;
• and
• R10, X and Y are independently selected from the group consisting of hydrogen, alkyl, thiol, hydroxy, thioalkyl, alkoxy, substituted alkyl, carbocyclic, substituted carboxyclic, heterocyclic and substituted heterocyclic;
• P and q are selected from 0, 1, 2 and 3;
• and
• the agriculturally acceptable salts of compounds of formula I.

4 An insecticide according to claim 2 wherein

• R1 is selected from the group consisting of hydroxy, C1 to C6 alkyl, halogenated C1 to C4 alkyl;
• the group NR6OH wherein R6 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, carbocyclic and substituted carbocyclic;
• and
• the group NR7R8 wherein R7 and R8 are independently selected from hydrogen and C1 to C4 alkyl;
• R2 is selected from the group consisting of hydrogen C1 to C8 alkyl, halo —(C1 to C6) alkyl and C1 to C6 alkyl substituted by the group of formula
• 43
• wherein R14 and R15 are independently selected from the group consisting of hydrogen and C1 to C4 alkyl;
• and
• and the group wherein R2 is linked to R1 to provide the group —R1 —R2— of formula
• —(CR12R13)O—
• where R12 and R13 are independently selected from hydrogen, C1 to C4 alkyl and C1 to C4 haloalkyl;
• R3 is selected from the group consisting of hydrogen, C1 to C6 alkyl, C1 to C6 alkanoyl, C1 to C6 haloalkyl and C1 to C6 alkyl and C1 to C6 alkyl substituted by the group of formula
• 44
• wherein R14 and R15 are independently selected from the group consisting of hydrogen and C1 to C4 alkyl;
• p and q are zero;
• R10 is hydrogen and
• X and Y are independently selected from the group consisting of hydrogen, C1 to C4 alkyl thiol, aryl, hydroxyaryl, acyl, aryl substituted C1 to C4 alkyl, heterocyclic, thio- C1 to C4 alkyl, amino- C1 to C4 alkyl and hydroxyalkyl.

An insecticide comprising the compound of formula III

• 48
• wherein
• R1 is selected from the group consisting of hydroxy, C1 to C6 alkyl, halogenated C1 to C6 alkyl and the group NR7R8 wherein R7 and R8 are independently selected from hydrogen and C1 to C4 alkyl;
• the group NR6OH wherein R6 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, carbocyclic and substituted carbocyclic;
• and
• the group NR7R8 wherein R7 and R8 are independently selected from hydrogen and C1 to C4 alkyl;
• R2 is selected from the group consisting of hydrogen C1 to C8 alkyl, halo —(C1 to C6) alkyl and C1 to C6 alkyl substituted by the group of formula
• 49
• wherein R14 and R15 are independently selected from the group consisting of hydrogen and C1 to C4 alkyl;
• and
• and the group wherein R2 is linked to R1 to provide the group —R1—R2— of formula
• —(CR12R13)O—
• where R12 and R13 are independently selected from hydrogen, C1 to C4 alkyl and C1 to C4 haloalkyl;
• R3 is selected from the group consisting of hydrogen, C1 to C6 alkyl, C1 to C6 alkanoyl, C1 to C6 haloalkyl and C1 to C6 alkyl and C1 to C6 alkyl substituted by the group of formula
• 50
• wherein R14 and R15 are independently selected from the group consisting of hydrogen and C1 to C4 alkyl;
• X and Y are independently selected from the group consisting of hydrogen, C1 to C4 alkyl thiol, aryl, hydroxyaryl, acyl, aryl substituted C1 to C4 alkyl, heterocyclic, thio- C1 to C4 alkyl, amino- C1 to C4 alkyl and hydroxyalkyl.

An insecticide selected from the group consisting of 3-Methyl-2-(phosphonomethyl-amino)-butyric acid;

• [(1-Hydroxycarbamoyl-3-methyl-butylamino)-methyl]-phosphonic acid monomethyl ester;
• [(1-Hydroxycarbamoyl-2-phenyl-ethylamino)-methyl)-phosphonic acid monomethyl ester;
• 2-Methylamino-propionic acid;
• -Phenyl-2-(phosphonomethyl-amino)-propionic acid;
• N-Hydroxy-2-methylamino-propionamide;
• [(1-Hydroxycarbamoyl-ethylamino)-methyl]-phosphonic acid monomethyl ester;
• 4-(2-methylpropyl)-3-(dimethoxy-phosphonomethyl)-2,2-bis-trifluoromethyl-oxazolidin-5-one;
• 2-Acetylamino-N-hydroxy-3-phenyl-propionamide;
• 2-[(Dimethoxy-phosphorylmethyl)-amino]-3-hydroxy-butyric acid methyl ester;
• 4-Benzyl-3-bromomethyl-2,2-bis-trifluoromethyl-oxazolidin-5-one;
• 2-[Bis-(dimethoxy-phosphorylmethyl)-amino]-3-methyl-butyric acid methyl ester;
• 4-Benzyl-3-methyl-2,2-bis-trifluoromethyl-oxazolidin-5-one;
• [(1-Hydroxycarbamoyl-2-methyl-propylamino)-methyl]-phosphonic acid;
• 3-Methyl-2-methylamino-pentanoic acid;
• [(1-Hydroxycarbamoyl-3-methyl-butylamino)-methyl]-phosphonic acid;
• and 2-Amino-1-(2-benzyloxymethyl-pyrrolidin-1-yl)-3-methyl-butan-1-one;
• and the salts thereof.

A method for the preparation of an insecticide of formula III

• 54
• comprising reacting an amino acid or derivative thereof of formula (V)
• 55
• wherein Z is —CN or COOR5
• wherein R5 is selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, cycloalkyl, substituted cycloalkyl, heterocyclic and substituted heterocyclic;
• with a compound for formula
• 56
• wherein R12 and R13 are independently selected from hydrogen, halogen, alkyl and haloalkyl;
• reacting the intermediate with a phosphite of formula HPO(OR14)(OR15) wherein R14 and R15 are independently selected from the group consisting of alkyl, to provide the compound of formula III and optionally hydrolysing the ester groups to provide a compound of formula III wherein R14 and R15 are hydrogen and R1 is hydroxy.