N-[(5-Halo-2,6-(substituted)pyrazinyl)methylene]amine antimicrobial compounds, compositions and use

Claim 1

A compound of the formula: ##STR4## wherein: Hal is bromine or chlorine; and R is halo; mono- or di-substituted mono- or diloweralkylamino wherein the loweralkyl substituents are hydroxy or loweralkanoyloxy; 4-morpholino; thiocyano; mercapto; straight or branched chain C 1-8 alkylthio; mono- or di-substituted loweralkylthio wherein the substituents are hydroxy, amino, loweralkylanoylamino, or loweralkoxycarbonyl; arylthio; loweralkylsulfoxy; or loweralkylsulfonyl; R 1 is hydrogen; or loweralkyl; R 2 is (CH 2 ) n COOR a , where R a is hydrogen, loweralkyl, or benzyl; and n is 1 to 3; R 1 and R 2 are taken together with an oxygen or nitrogen atom to form morpholino, piperazinyl, or piperazinyl which is N-loweralkyl substituted; R 3 is hydrogen; straight or branched C 1-8 alkyl; aryl; aryl substituted with up to two members selected from the group consisting of C 1-3 alkyl, C 1-3 alkoxy, halo, and mono- or di-C 1-3 alkyl substituted amino; heteroaryl; formylC 2-4 alkenyl; or C 2-4 alkenyl; and R 4 is straight or branched C 1-8 alkyl; loweralkoxy; hydroxy; loweralkoxycarbonylmethyl; benzyl; or benzyl substituted with up to two members selected from the group consisting of halo, loweralkyl, and loweralkoxy.

Claim 7

A method of inhibiting the growth of bacteria and fungi comprising contacting said bacteria and fungi with a bactericidally and fungicidally effective amount of a compound of the formula: ##STR6## wherein: Hal is bromine or chlorine; and R is halo; mono- or di-substituted mono- or diloweralkylthio wherein the loweralkyl substituents are hydroxy or loweralkanoyloxy; 4-morpholino; thiocyano; mercapto; straight or branched chain C 1-8 alkylthio; mono- or di-substituted loweralkylthio wherein the substituents are hydroxy, amino, loweralkanoylamino, or loweralkoxycarbonyl; arylthio; loweralkylsulfoxy; or loweralkylsulfonyl; R 1 is hydrogen; or loweralkyl; R 2 is (CH 2 ) n COOR a , where R a is hydrogen, loweralkyl, or benzyl; and n is 1 to 3; R 1 and R 2 are taken together with an oxygen or nitrogen atom to form morpholino, piperazinyl, or piperazinyl which is N-loweralkyl substituted; R 3 is hydrogen; straight or branched C 1-8 alkyl; aryl; aryl substituted with up to two members selected from the group consisting of C 1-3 alkyl, C 1-3 alkoxy, halo, and mono- or di-C 1-3 alkyl substituted amino; heteroaryl; formylC 2-4 alkenyl; or C 2-4 alkenyl; and R 4 is straight or branched C 1-8 alkyl; loweralkoxy; hydroxy; loweralkoxycarbonylmethyl; benzyl; or benzyl substituted with up to two members selected from the group consisting of halo, loweralkyl, and loweralkoxy.

Claim 8

A method of inhibiting the growth of bacteria and fungi comprising contacting said bacteria and fungi with a bactericidally and fungicidally effective amount of a compound of the formula: ##STR6## wherein: Hal is bromine or chlorine; and R is halo; mono- or di-substituted mono- or diloweralkylthio wherein the loweralkyl substituents are hydroxy or loweralkanoyloxy; 4-morpholino; thiocyano; mercapto; straight or branched chain C 1-8 alkylthio; mono- or di-substituted loweralkylthio wherein the substituents are hydroxy, amino, loweralkanoylamino, or loweralkoxycarbonyl; arylthio; loweralkylsulfoxy; or loweralkylsulfonyl; R 1 is hydrogen; or loweralkyl; R 2 is (CH 2 ) n COOR a , where R a is hydrogen, loweralkyl, or benzyl; and n is 1 to 3; R 1 and R 2 are taken together with an oxygen or nitrogen atom to form morpholino, piperazinyl, or piperazinyl which is N-loweralkyl substituted; R 3 is hydrogen; straight or branched C 1-8 alkyl; aryl; aryl substituted with up to two members selected from the group consisting of C 1-3 alkyl, C 1-3 alkoxy, halo, and mono- or di-C 1-3 alkyl substituted amino; heteroaryl; formylC 2-4 alkenyl; or C 2-4 alkenyl; and R 4 is straight or branched C 1-8 alkyl; loweralkoxy; hydroxy; loweralkoxycarbonylmethyl; benzyl; or benzyl substituted with up to two members selected from the group consisting of halo, loweralkyl, and loweralkoxy.

Claim 10

A method of inhibiting the growth of bacteria and fungi in aqueous slurries of clays or pigments comprising incorporating into said aqueous slurry so as to contact said bacteria and fungi, at least a bactericidally and fungicidally effective amount of a compound of the formula: ##STR7## wherein: Hal is bromine or chlorine; and R is halo; mono- or di-substituted mono- or diloweralkylamino wherein the loweralkyl substituents are hydroxyl or loweralkanoyloxy; 4-morpholino; thiocyano; mercapto; straight or branched chain C 1-8 alkylthio; mono- or di-substituted loweralkylthio wherein the substituents are hydroxy, amino, loweralkanoylamino, or loweralkoxycarbonyl; arylthio; loweralkylsulfoxy; or loweralkylsulfonyl; R 1 is hydrogen; or loweralkyl; R 2 is (CH 2 ) n COOR a , where R a is hydrogen, loweralkyl, or benzyl; and n is 1 to 3; R 1 and R 2 are taken together with an oxygen or nitrogen atom to form morpholino, piperazinyl, or piperazinyl which is N-loweralkyl substituted; R 3 is hydrogen; straight or branched C 1-8 alkyl; aryl; aryl substituted with up to two members selected from the group consisting of C 1-3 alkyl, C 1-3 alkoxy, halo, and mono- or di-C 1-3 alkyl substituted amino; heteroaryl; formylC 2-4 alkenyl; or C 2-4 alkenyl; and R 4 is straight or branched C 1-8 alkyl; loweralkoxy; hydroxy; loweralkoxycarbonylmethyl; benzyl; or benzyl substituted with up to two members selected from the group consisting of halo, loweralkyl, and loweralkoxy.

Claim 11

A method of inhibiting the growth of bacteria and fungi in aqueous slurries of clays or pigments comprising incorporating into said aqueous slurry so as to contact said bacteria and fungi, at least a bactericidally and fungicidally effective amount of a compound of the formula: ##STR7## wherein: Hal is bromine or chlorine; and R is halo; mono- or di-substituted mono- or diloweralkylamino wherein the loweralkyl substituents are hydroxyl or loweralkanoyloxy; 4-morpholino; thiocyano; mercapto; straight or branched chain C 1-8 alkylthio; mono- or di-substituted loweralkylthio wherein the substituents are hydroxy, amino, loweralkanoylamino, or loweralkoxycarbonyl; arylthio; loweralkylsulfoxy; or loweralkylsulfonyl; R 1 is hydrogen; or loweralkyl; R 2 is (CH 2 ) n COOR a , where R a is hydrogen, loweralkyl, or benzyl; and n is 1 to 3; R 1 and R 2 are taken together with an oxygen or nitrogen atom to form morpholino, piperazinyl, or piperazinyl which is N-loweralkyl substituted; R 3 is hydrogen; straight or branched C 1-8 alkyl; aryl; aryl substituted with up to two members selected from the group consisting of C 1-3 alkyl, C 1-3 alkoxy, halo, and mono- or di-C 1-3 alkyl substituted amino; heteroaryl; formylC 2-4 alkenyl; or C 2-4 alkenyl; and R 4 is straight or branched C 1-8 alkyl; loweralkoxy; hydroxy; loweralkoxycarbonylmethyl; benzyl; or benzyl substituted with up to two members selected from the group consisting of halo, loweralkyl, and loweralkoxy.

Claim 13

A method of inhibiting the growth of bacteria and fungi in latex paints and latex emulsions and adhesives comprising incorporating into said latex paints, emulsions, and adhesives so as to contact said bacteria and fungi, at least a bactericidally and fungicidally effective amount of a compound of the formula: ##STR8## wherein: Hal is bromine or chlorine; and R is halo; mono- or di-substituted mono- or diloweralkylamino wherein the loweralkyl substituents are hydroxy or loweralkanoyloxy; 4-morpholino; thiocyano; mercapto; straight or branched chain C 1-8 alkylthio; mono- or di-substituted loweralkylthio wherein the substituents are hydroxy, amino, loweralkanoylamino, or loweralkoxycarbonyl; arylthio; loweralkylsulfoxy; or loweralkylsulfonyl; R 1 is hydrogen; or loweralkyl; R 2 is (CH 2 ) n COOR a , where R a is hydrogen, loweralkyl, or benzyl; and n is 1 to 3; R 1 and R 2 are taken together with an oxygen or nitrogen atom to form morpholino, piperazinyl, or piperazinyl which is N-loweralkyl substituted; R 3 is hydrogen; straight or branched C 1-8 alkyl; aryl; aryl substituted with up to two members selected from the group consisting of C 1-3 alkyl, C 1-3 alkoxy, halo, and mono- or di-C 1-3 alkyl substituted amino; heteroaryl; formylC 2-4 alkenyl; or C 2-4 alkenyl; and R 4 is straight or branched C 1-8 alkyl; loweralkoxy; hydroxy; loweralkoxycarbonylmethyl; benzyl; or benzyl substituted with up to two members selected from the group consisting of halo, loweralkyl, and loweralkoxy.

Claim 14

A method of inhibiting the growth of bacteria and fungi in latex paints and latex emulsions and adhesives comprising incorporating into said latex paints, emulsions, and adhesives so as to contact said bacteria and fungi, at least a bactericidally and fungicidally effective amount of a compound of the formula: ##STR8## wherein: Hal is bromine or chlorine; and R is halo; mono- or di-substituted mono- or diloweralkylamino wherein the loweralkyl substituents are hydroxy or loweralkanoyloxy; 4-morpholino; thiocyano; mercapto; straight or branched chain C 1-8 alkylthio; mono- or di-substituted loweralkylthio wherein the substituents are hydroxy, amino, loweralkanoylamino, or loweralkoxycarbonyl; arylthio; loweralkylsulfoxy; or loweralkylsulfonyl; R 1 is hydrogen; or loweralkyl; R 2 is (CH 2 ) n COOR a , where R a is hydrogen, loweralkyl, or benzyl; and n is 1 to 3; R 1 and R 2 are taken together with an oxygen or nitrogen atom to form morpholino, piperazinyl, or piperazinyl which is N-loweralkyl substituted; R 3 is hydrogen; straight or branched C 1-8 alkyl; aryl; aryl substituted with up to two members selected from the group consisting of C 1-3 alkyl, C 1-3 alkoxy, halo, and mono- or di-C 1-3 alkyl substituted amino; heteroaryl; formylC 2-4 alkenyl; or C 2-4 alkenyl; and R 4 is straight or branched C 1-8 alkyl; loweralkoxy; hydroxy; loweralkoxycarbonylmethyl; benzyl; or benzyl substituted with up to two members selected from the group consisting of halo, loweralkyl, and loweralkoxy.

Claim 16

A method of inhibiting the growth of bacteria and fungi in metalworking fluids comprising incorporating into said fluids so as to contact said bacteria and fungi, at least a bactericidally and fungicidally effective amount of a compound of the formula: ##STR9## wherein: Hal is bromine or chlorine; and R is halo; mono- or di-substituted mono- or diloweralkylamino wherein the loweralkyl substituents are hydroxy or loweralkanoyloxy, 4-morpholino; thiocyano; mercapto; straight or branched chain C 1-8 alkylthio; mono- or di-substituted loweralkylthio wherein the substituents are hydroxy, amino, loweralkanoylamino, or loweralkoxycarbonyl, arylthio; loweralkylsulfoxy; or loweralkylsulfonyl; R 1 is hydrogen; or loweralkyl; R 2 is (CH 2 ) n COOR a , where R a is hydrogen, loweralkyl, or benzyl; and n is 1 to 3; R 1 and R 2 are taken together with an oxygen or nitrogen atom to form morpholino, piperazinyl, or piperazinyl which is N-loweralkyl substituted; R 3 is hydrogen; straight or branched C 1-8 alkyl; aryl; aryl substituted with up to two members selected from the group consisting of C 1-3 alkyl, C 1-3 alkoxy, halo, and mono- or di-C 1-3 alkyl substituted amino; heteroaryl; formylC 2-4 alkenyl; or C 2-4 alkenyl; and R 4 is straight or branched C 1-8 alkyl; loweralkoxy; hydroxy; loweralkoxycarbonylmethyl; benzyl; or benzyl substituted with up to two members selected from the group consisting of halo, loweralkyl, and loweralkoxy.

Claim 17

A method of inhibiting the growth of bacteria and fungi in metalworking fluids comprising incorporating into said fluids so as to contact said bacteria and fungi, at least a bactericidally and fungicidally effective amount of a compound of the formula: ##STR9## wherein: Hal is bromine or chlorine; and R is halo; mono- or di-substituted mono- or diloweralkylamino wherein the loweralkyl substituents are hydroxy or loweralkanoyloxy, 4-morpholino; thiocyano; mercapto; straight or branched chain C 1-8 alkylthio; mono- or di-substituted loweralkylthio wherein the substituents are hydroxy, amino, loweralkanoylamino, or loweralkoxycarbonyl, arylthio; loweralkylsulfoxy; or loweralkylsulfonyl; R 1 is hydrogen; or loweralkyl; R 2 is (CH 2 ) n COOR a , where R a is hydrogen, loweralkyl, or benzyl; and n is 1 to 3; R 1 and R 2 are taken together with an oxygen or nitrogen atom to form morpholino, piperazinyl, or piperazinyl which is N-loweralkyl substituted; R 3 is hydrogen; straight or branched C 1-8 alkyl; aryl; aryl substituted with up to two members selected from the group consisting of C 1-3 alkyl, C 1-3 alkoxy, halo, and mono- or di-C 1-3 alkyl substituted amino; heteroaryl; formylC 2-4 alkenyl; or C 2-4 alkenyl; and R 4 is straight or branched C 1-8 alkyl; loweralkoxy; hydroxy; loweralkoxycarbonylmethyl; benzyl; or benzyl substituted with up to two members selected from the group consisting of halo, loweralkyl, and loweralkoxy.

Claim 19

A method for protecting soil, seeds, plants and crops against destructive bacteria and fungi which comprises applying thereto a bactericidally and fungicidally effective amount of a compound of the formula: ##STR10## wherein: Hal is bromine or chlorine; and R is halo; mono- or di-substituted mono- or diloweralkylamino wherein the loweralkyl substituents are hydroxy or loweralkanoyloxy; 4-morpholino; thiocyano; mercapto; straight or branched chain C 1-8 alkylthio; mono- or di-substituted loweralkylthio wherein the substituents are hydroxy, amino, loweralkanoylamino, or loweralkoxycarbonyl; arylthio; loweralkylsulfoxy; or loweralkylsulfonyl; R 1 is hydrogen; or loweralkyl; R 2 is (CH 2 ) n COOR a , where R a is hydrogen, loweralkyl, or benzyl; and n is 1 to 3; R 1 and R 2 are taken together with an oxygen or nitrogen atom to form morpholino, piperazinyl, or piperazinyl which is N-loweralkyl substituted; R 3 is hydrogen; straight or branched C 1-8 alkyl; aryl; aryl substituted with up to two members selected from the group consisting of C 1-3 alkyl, C 1-3 alkoxy, halo, and mono- or di-C 1-3 alkyl substituted amino; heteroaryl; formylC 2-4 alkenyl; or C 2-4 alkenyl; and R 4 is straight or branched C 1-8 alkyl; loweralkoxy; hydroxy; loweralkoxycarbonylmethyl; benzyl; or benzyl substituted with up to two members selected from the group consisting of halo, loweralkyl, and loweralkoxy.

Claim 20

A method for protecting soil, seeds, plants and crops against destructive bacteria and fungi which comprises applying thereto a bactericidally and fungicidally effective amount of a compound of the formula: ##STR10## wherein: Hal is bromine or chlorine; and R is halo; mono- or di-substituted mono- or diloweralkylamino wherein the loweralkyl substituents are hydroxy or loweralkanoyloxy; 4-morpholino; thiocyano; mercapto; straight or branched chain C 1-8 alkylthio; mono- or di-substituted loweralkylthio wherein the substituents are hydroxy, amino, loweralkanoylamino, or loweralkoxycarbonyl; arylthio; loweralkylsulfoxy; or loweralkylsulfonyl; R 1 is hydrogen; or loweralkyl; R 2 is (CH 2 ) n COOR a , where R a is hydrogen, loweralkyl, or benzyl; and n is 1 to 3; R 1 and R 2 are taken together with an oxygen or nitrogen atom to form morpholino, piperazinyl, or piperazinyl which is N-loweralkyl substituted; R 3 is hydrogen; straight or branched C 1-8 alkyl; aryl; aryl substituted with up to two members selected from the group consisting of C 1-3 alkyl, C 1-3 alkoxy, halo, and mono- or di-C 1-3 alkyl substituted amino; heteroaryl; formylC 2-4 alkenyl; or C 2-4 alkenyl; and R 4 is straight or branched C 1-8 alkyl; loweralkoxy; hydroxy; loweralkoxycarbonylmethyl; benzyl; or benzyl substituted with up to two members selected from the group consisting of halo, loweralkyl, and loweralkoxy.