Benzo-1,2,4-triazines

Claim 2

A compound of the formula: ##SPC34## wherein each of X and X', independently of the other, is hydrogen; halogeno, alkyl of 1 to 6 carbon atoms, unsubstituted or substituted by nitro, alkoxy of 1 to 5 carbon atoms, or up to 5 halogen atoms; or alkoxy of 1 to 6 carbon atoms, unsubstituted or substituted by halogen or nitro; and B is alkyl of 1 to 6 carbon atoms; alkenyl of 2 to 6 carbon atoms or benzyl.

Claim 3

A compound according to claim 1 wherein each of X and X', independently of the other, is hydrogen, chloro, bromo, fluoro, methyl, ethyl, methoxy, ethoxy or trifluoromethyl; and B is alkyl of 1 to 4 carbon atoms, allyl or benzyl.

Claim 4

The compound according to claim 1 which is: ##SPC35##

Claim 5

A compound of the formula: ##SPC36## wherein each of X and X', independently of the other, is hydrogen; halogeno, alkyl of 1 to 6 carbon atoms, unsubstituted or substituted by nitro, alkoxy of 1 to 5 carbon atoms, or up to 5 halogen atoms; or alkoxy of 1 to 6 carbon atoms, unsubstituted or substituted by halogeno or nitro; and R' is hydrogen; acetylmethyl; alkyl of 2 to 17 carbon atoms, substituted by nitro, alkoxy of 1 to 4 carbon atoms, or 1 to 5 halogen atoms; or phenyl, unsubstituted or substituted by up to two substituents selected from the group consisting of halogeno, nitro, alkyl of 1 to 4 carbon atoms and haloalkyl of 1 to 4 carbon atoms.

Claim 6

A compound of the formula: ##SPC36## wherein each of X and X', independently of the other, is hydrogen; halogeno, alkyl of 1 to 6 carbon atoms, unsubstituted or substituted by nitro, alkoxy of 1 to 5 carbon atoms, or up to 5 halogen atoms; or alkoxy of 1 to 6 carbon atoms, unsubstituted or substituted by halogeno or nitro; and R' is hydrogen; acetylmethyl; alkyl of 2 to 17 carbon atoms, substituted by nitro, alkoxy of 1 to 4 carbon atoms, or 1 to 5 halogen atoms; or phenyl, unsubstituted or substituted by up to two substituents selected from the group consisting of halogeno, nitro, alkyl of 1 to 4 carbon atoms and haloalkyl of 1 to 4 carbon atoms.

Claim 7

A compound according to claim 4 wherein each of X and X', independently of the other, is hydrogen, chloro, bromo, fluoro, methyl, ethyl, methoxy, ethoxy or trifluoromethyl; and R' is hydrogen, acetylmethyl, phenyl, nitrophenyl or dinitrophenyl.

Claim 8

The compound according to claim 4 which is: ##SPC37##

Claim 9

The compound according to claim 4 which is: ##SPC38##

Claim 10

The compound according to claim 4 which is: ##SPC39##

Claim 11

The compound according to claim 4 which is: ##SPC40##

Claim 12

The compound according to claim 4 which is: ##SPC41##

Claim 13

A compound of the formula: ##SPC42## wherein each of X and X', independently of the other, is hydrogen; halogeno, alkyl of 1 to 6 carbon atoms, unsubstituted or substituted by nitro, alkoxy of 1 to 5 carbon atoms, or up to 5 halogen atoms; or alkoxy of 1 to 6 carbon atoms, unsubstituted or substituted by halogeno or nitro; and each of R 3 and R 4 , when taken separately from and independently of the other, is hydrogen, alkyl of 1 to 6 carbon atoms, unsubstituted or substituted by methoxy, ethoxy, hydroxy, halogeno, cyano, methylamino, ethylamino, dimethylamino, diethylamino, carbomethoxy or carbethoxy; alkenyl of 2 to 4 carbon atoms, unsubstituted or substituted by methoxy, ethoxy, hydroxy or halogeno; R 3 is phenyl or cycloalkyl and R 4 is hydrogen; or R 3 and R 4 , when taken collectively, together with the nitrogen atom to which they are attached, are pyrrolidino, piperidino, piperazine, hexamethyleneimino, morpholino, or N-methylpiperazino.

Claim 14

A compound of the formula: ##SPC42## wherein each of X and X', independently of the other, is hydrogen; halogeno, alkyl of 1 to 6 carbon atoms, unsubstituted or substituted by nitro, alkoxy of 1 to 5 carbon atoms, or up to 5 halogen atoms; or alkoxy of 1 to 6 carbon atoms, unsubstituted or substituted by halogeno or nitro; and each of R 3 and R 4 , when taken separately from and independently of the other, is hydrogen, alkyl of 1 to 6 carbon atoms, unsubstituted or substituted by methoxy, ethoxy, hydroxy, halogeno, cyano, methylamino, ethylamino, dimethylamino, diethylamino, carbomethoxy or carbethoxy; alkenyl of 2 to 4 carbon atoms, unsubstituted or substituted by methoxy, ethoxy, hydroxy or halogeno; R 3 is phenyl or cycloalkyl and R 4 is hydrogen; or R 3 and R 4 , when taken collectively, together with the nitrogen atom to which they are attached, are pyrrolidino, piperidino, piperazine, hexamethyleneimino, morpholino, or N-methylpiperazino.

Claim 15

A compound according to claim 11 wherein each of X and X', independently of the other, is hydrogen, chloro, bromo, fluoro, methyl, ethyl, methoxy, ethoxy or trifluoromethyl; and both of R 3 and R 4 are hydrogen; R 3 is hydrogen and R 4 is alkyl of 1 to 4 carbon atoms, unsubstituted or substituted by hydroxy, methoxy or ethoxy; cyclohexyl or phenyl; each of R 3 and R 4 is alkyl of 1 to 4 carbon atoms; or R 3 and R 4 , taken collectively together with the nitrogen atom to which they are attached, are pyrrolidino, piperidino, piperazino, hexamethyleneimino, morpholino or N-methylpiperazino.

Claim 16

The compound according to claim 11 which is: ##SPC43##

Claim 17

The compound according to claim 11 which is: ##SPC44##

Claim 18

The compound according to claim 11 which is: ##SPC45##

Claim 19

The compound according to claim 11 which is: ##SPC46##

Claim 20

The compound according to claim 11 which is: ##SPC47##

Claim 21

The compound according to claim 11 which is: ##SPC48##

Claim 22

The compound according to claim 11 which is: ##SPC49##

Claim 23

The compound according to claim 11 which is: ##SPC50##

Claim 24

The compound according to claim 11 which is: ##SPC51##

Claim 25

The compound according to claim 11 which is: ##SPC52##

Claim 26

The compound according to claim 11 which is: ##SPC53##

Claim 27

Process for the preparation of a compound of the formula: ##SPC54## wherein each of X and X', independently of the other, is hydrogen; halogeno, alkyl of 1 to 6 carbon atoms, unsubstituted or substituted by nitro, alkoxy of 1 to 5 carbon atoms, or up to 5 halogen atoms; or alkoxy or 1 to 6 carbon atoms, unsubstituted or substituted by halogeno or nitro; and each of R 3 and R 4 , when taken separately from and independently of the other, is hydrogen, alkyl of 1 to 6 carbon atoms, unsubstituted or substituted by methoxy, ethoxy, hydroxy, halogeno, cyano, methylamino, ethylamino, dimethylamino, diethylamino, carbomethoxy or carbethoxy; alkenyl of 2 to 4 carbon atoms, unsubstituted or substituted by methoxy, ethoxy, hydroxy or halogeno; R 3 is phenyl or cycloalkyl and R 4 is hydrogen; or R 3 and R 4 , when taken collectively, together with the nitrogen atom to which they are attached, are pyrrolidino, piperidino, piperazino, hexamethyleneimino, morpholino, or N-methylpiperazino, which comprises reacting an N-oxide of the formula: ##SPC55## in which X and X' are as herein defined with an amine of the formula ##EQU3## in which R 3 and R 4 are as herein defined at temperatures of from 0°C to 150°C.

Claim 28

Process for the preparation of a compound of the formula: ##SPC54## wherein each of X and X', independently of the other, is hydrogen; halogeno, alkyl of 1 to 6 carbon atoms, unsubstituted or substituted by nitro, alkoxy of 1 to 5 carbon atoms, or up to 5 halogen atoms; or alkoxy or 1 to 6 carbon atoms, unsubstituted or substituted by halogeno or nitro; and each of R 3 and R 4 , when taken separately from and independently of the other, is hydrogen, alkyl of 1 to 6 carbon atoms, unsubstituted or substituted by methoxy, ethoxy, hydroxy, halogeno, cyano, methylamino, ethylamino, dimethylamino, diethylamino, carbomethoxy or carbethoxy; alkenyl of 2 to 4 carbon atoms, unsubstituted or substituted by methoxy, ethoxy, hydroxy or halogeno; R 3 is phenyl or cycloalkyl and R 4 is hydrogen; or R 3 and R 4 , when taken collectively, together with the nitrogen atom to which they are attached, are pyrrolidino, piperidino, piperazino, hexamethyleneimino, morpholino, or N-methylpiperazino, which comprises reacting an N-oxide of the formula: ##SPC55## in which X and X' are as herein defined with an amine of the formula ##EQU3## in which R 3 and R 4 are as herein defined at temperatures of from 0°C to 150°C.

Claim 29

A process according to claim 24 wherein an inert organic solvent or water is used as a diluent.

Claim 30

A process according to claim 25 wherein the diluent is a polar organic solvent, a nitrile, dimethylformamide, an ether, a heteroaromatic compound, nitrobenzene or a mixture thereof.

Claim 31

A process according to claim 25 wherein the diluent is an excess of amine.

Claim 32

A process as defined in claim 24 wherein the product is precipitated in the form of its ammonium salt and the ammonium salt is treated with a suitable organic or inorganic acid to produce the free base.

Claim 33

A process as defined in claim 24 wherein the temperature is between 20°C and 80°C.

Claim 34

A process as defined in claim 24 wherein the reaction is carried out at atmospheric pressure.

Claim 35

A process as defined in claim 24 wherein the reaction is carried out at elevated pressure.

Claim 36

A process as defined in claim 24 which comprises reacting at least 1 mol of amine per mol of N-oxide.

Claim 37

A process as defined in claim 32 wherein 1 to 20 mols of amino compound are used per mol of N-oxide.

Claim 38

A process as defined in claim 33 wherein 2 to 5 mols of amino compound are used per mol of N-oxide.