Novel sulfonamides derived from substituted 2-amino-1,2,4-triazolo(1,5-a)pyrimidines and compositions and methods of controlling undesired vegetation

Claim 2

A compound having the formula: wherein Ar represents a substituted or unsubstituted aromatic or heteroaromatic ring system, R represents hydrogen, alkyl, alkenyl, alkynyl, arylalkyl, substituted arylalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, dialkylaminocarbonyl, alkylsulfonyl, arylsulfonyl, alkylthiocarbonyl or arylthiocarbonyl and X, Y and Z independently represent hydrogen, alkyl, haloalkyl, hydroxy, alkoxy, haloalkoxy, aryl, substituted aryl, halogen, alkylthio, amino, carboxylic acids and esters or two adjacent substituents are joined together in a cyclic structure, or the pyrimidine ring may be reduced to form a 4,5,6,7-tetra hydro-1,2,4-triazolo[1,5-a]pyrimidine ring.

Claim 3

A compound as claimed in Claim 1 wherein Ar is wherein R 1 represents halo, -NO 2 , phenyl, -CF 3 , -OCF 3 , -OCF 2 CF 2 H, -OCF 2 CCl 2 H, -OCH 2 CF 3 , -SCF 3 , -SCF 2 C F 2 H, -SCF 2 CCl 2 H, -SOCF 3 , -SOCF 2 CF 2 H, -SOCF 2 CCl 2 H, -SO 2 CF 3 , -SOCF 2 CF 2 H, -SO 2 CF 2 CCl 2 H, -SR 6 , -SOR 6 . -SO 2 R 6 , - CN , -COOR 7 , -CONRB(R 9 ). -SO 2 NR 8 R 9 . -SO 3 R 8 and -SO 3 CH 2 CF 3 ; R 2 and R 4 represent H, halo, C l -C 4 alkyl and -OR ; R 3 is H ; and R 5 represents H, C 1 to C 4 alkyl, halo, N0 2 , CF 3 , -OCF 3 , -OCF 2 CF 2 H. -OCF 2 CCl 2 H, -OCH 2 CF 3 , -SCF 3 , -SCF 2 CF 2 H, -SCF 2 CCl 2 H, -SOCF 3 , -SOCF 2 CF 2 H, -SOCF 2 CCl 2 H, -SO 2 CF 3 , -SO 2 CF 2 CF 2 H, -SO 2 CF 2 CCl 2 H, -SR 6 , -SOR 6 . -SO 2 R 6 , -C N , -C OO R 7 , -CONR (R 9 ), -SO 3 R 8 , and -SO 3 CH 2 CF 3 wherein R 6 represents aryl or C 1 -C 4 alkyl, R 7 represents C 1 -C 6 alkyl, alkenyl or alkynyl and R 8 and R 9 individually represent C l -C 4 alkyl; and X, Y and Z represent H, C 1 -C 4 alkyl or C 1 -C 4 alkoxy groups, or X and Y or Y and Z can be joined to form a cyclo alkyl ring or X and Y or Y and Z can be joined to form a ring containing a heteroatom.

Claim 4

A compound as claimed in Claim 2 wherein X and Z independently represent hydrogen, C 1 to C 4 lower alkyl or alkoxy group and Y is hydrogen.

Claim 5

A compound as claimed in Claim 2 wherein X and Z are methyl and Y is hydrogen.

Claim 6

A compound as claimed in Claim 1 wherein Ar is wherein X represents 0 or S, and R 1 , R 2 and R 3 are each independently hydrogen, alkyl or halo.

Claim 7

A compound as claimed in Claim 1 wherein Ar is wherein X represents O or S, and R 1 , R 2 and R 3 are each independently hydrogen, alkyl, halo or -COOR 4 wherein R 4 represents C 1 -C 6 alkyl, alkenyl or alkynyl.

Claim 8

A herbicidal composition comprising an inert carrier in admixture with a herbicidally effective amount of at least one compound as claimed in any one of Claims 1 to 6.

Claim 9

A method of controlling undesired vegetation which comprises the application of a herbicidally effective amount of a compound as claimed in any one of Claims 1 to 6, or of a composition as claimed in Claim 7.

Claim 10

A method of preparing a compound as claimed in Claim 1 in which the group R is a hydrogen atom wherein a compound of the formula: wherein Ar represents a substituted or unsubstituted aromatic or heteroaromatic ring system is reacted under basic conditions with a compound of formula: wherein X, Y and Z are each independently hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, halogen, or two adjacent substituents are joined together in a cyclic structure.

Claim 11

A method as claimed in Claim 9 wherein the reaction is carried out in the presence of pyridine.

Claim 12

A method for the preparation of a compound as claimed in Claim 1 in which the group R is as defined in Claim 1 but is other than a hydrogen atom, which comprises reacting a compound of the formula: wherein X, Y, Z and Ar are as defined in Claim 1 with an electrophilic reagent of the formula RX, wherein R is as defined above.

Claim 13

A method as claimed in Claim 11 wherein the reaction is carried out in the presence of a base and a suitable solvent.

Claim 14

CLAIMS FOR AUSTRIA: 1. A herbicidal composition comprising an herbicidally effective compound of at least one compound having the formula: wherein Ar represents a substituted or unsubstituted aromatic or heteroaromatic ring system, R represents hydrogen, alkyl, alkenyl, alkynyl, arylalkyl, substituted arylalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, dialkylaminocarbonyl, alkylsulfonyl, arylsulfonyl, alkylthiocarbonyl or arylthiocarbonyl and X, Y and Z independently represent hydrogen, alkyl, haloalkyl, hydroxy, alkoxy, haloalkoxy, aryl, substituted aryl, halogen, alkylthio, amino, carboxylic acids and esters or two adjacent substituents are joined together in a cyclic structure, or the pyrimidine ring may be reduced to form a 4,5,6,7-tetra- hydro-1,2,4-triazolo[1,5-a]pyrimidine ring; in admixture with an inert carrier.

Claim 15

A composition as claimed in Claim 1 wherein Ar is wherein R 1 represents halo, -NO 2 , phenyl, -CF 3 , -OCF 3 , -OCF 2 CF 2 H, -OCF 2 CCl 2 H, -OCH 2 CF 3 , -SCF 3 , -SCF 2 CF 2 H, -SCF 2 CCl 2 H, -SOCF 3 , -SOCF 2 CF 2 H, -SOCF 2 CCl 2 H, -SO 2 CF 3 , -SO 2 CF Z CF 2 H, -SO 2 CF 2 CCl 2 H. -SR 6 . -SOR 6 , -SO 2 R 6 , - CN , -COOR 7 , -CONR 8 (R 9 ), -SO 2 NR 8 R g , -SO 3 R 8 and -SO 3 CH 2 CF 3 ; R 2 and R 4 represent H, halo, C l -C 4 alkyl and -OR 8 ; R 3 is H; and R 5 represents H, C 1 to C 4 alkyl, halo, NO 2 , CF 3 , -OCF 3 , -OCF 2 CF 2 H, -OCF 2 CCl 2 H, -OCH 2 CF 3 , -SCF 3 , -SCF 2 CF 2 H, -SCF 2 CCl 2 H, -SOCF 3 , -SOCF 2 CF 2 H, -SOCF 2 CCl 2 H, -SO 2 CF 3 , -SO 2 CF 2 CF H, -SO 2 CF 2 CCl 2 H, -SR 6 , -SOR 6 , -SO 2 R 6 , -SO 2 CF 3 , -SO 2 CF 2 CF 2 H, -SO 2 CF 2 CCl 2 H, -SR 6 , -SOR 6 , -SO 2 R 6 , -CN, -COOR 7 , -CONR 8 (R 9 ). -SO 3 R 8 , and -SO 3 CH 2 CF 3 wherein R 6 represents aryl or C l -C 4 alkyl, R 7 represents C 1 -C 6 alkyl, alkenyl or alkynyl and R 8 and R 9 individually represent C 1 -C 4 alkyl; and X, Y and Z represent H, C 1 -C 4 alkyl or C 1 -C 4 alkoxy groups, or X and Y or Y and Z can be joined to form a cyclo alkyl ring or X and Y or Y and Z can be joined to form a ring containing a heteroatom.

Claim 16

A composition as claimed in Clam 2 wherein X and Z independently represent hydrogen, C 1 to C 4 lower alkyl or alkoxy group and Y is hydrogen.

Claim 17

A composition as claimed in Claim 1 wherein X and Z are methyl and Y is hydrogen.

Claim 18

A composition as claimed in Claim 1 wherein Ar is wherein X represents O or S, and R 1 . R 2 and R 3 are each independently hydrogen, alkyl or halo.

Claim 19

A composition as claimed in Claim 1 wherein Ar is wherein X represents O or S , and R 1 , R 2 and R 3 are each independently hydrogen, alkyl, halo or - COO R 4 wherein R 4 represents C 1 -C 6 alkyl, alkenyl or alkynyl.

Claim 20

Method of controlling undesired vegetation which comprises the application of a herbicidally effective amount of a compound as defined in any one of Claims 1 to 6 or of a composition as claimed in any one of Claims 1 to 6.

Claim 21

A method of preparing a compound as defined in Claim 1 in which R is other than a hydrogen atom wherein a compound of the formula: wherein Ar represents a substituted or unsubstituted aromatic or heteroaromatic ring system is reacted under basic conditions with a compound of formula: wherein X, Y and Z are each independently hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, halogen, or two adjacent substituents are joined together in a cyclic structure.

Claim 22

A method as claimed in Claim 8 wherein the reaction is carried out in the presence of pyridine.

Claim 23

A method for the preparation of a compound as defined in Claim 1 in which the group R is as defined in Claim I but is other than a hydrogen atom, which comprises reacting a compound of the formula: wherein X , Y, Z and Ar are as defined in Claim 1 with an electrophilic reagent of the formula RX, wherein R is as defined above.

Claim 24

A method as claimed in Claim 10 wherein the reaction is carried out in the presence of a base and a suitable solvent.