Novel substituted 1,2,4-triazolo- [1,5-a] pyrimidine-2-sulfonamides and compositions and methods of controlling undesired vegetation and suppressing the nitrification of ammonium nitrogen in soil

Claim 2

A compound having the formula: wherein Ar represents a substituted or unsubstituted aromatic or heteroaromatic ring system; V is H or R; X, Y and Z independently represent hydroxy, carboxyl, hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, aryl, substituted aryl, alkylthio, halogen, or two adjacent substituents are joined together in a cyclic structure and R represents alkyl, alkenyl, alkynyl, arylalkyl, substituted arylalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, dialkylaminocarbonyl, alkylsulfonyl, arylsulfonyl, alkylthiocarbonyl or arylthiocarbonyl.

Claim 3

A compound of Claim 1 wherein Ar represents substituted or unsubstituted phenyl; 1- or 2-naphthyl; 2-, 3- or 4-pyridyl; 2- or 3-thienyl; 2- or 3-furyl; 2-, 4- or 5-thiazolyl; 2-, 4- or 5-imidazolyl; 2-, 4-or 5-oxazolyl; 3-, 4- or 5-isothiazolyl; 3-, 4- or 5--isoxazolyl; 3-, 4- or 5-pyrazolyl; 2-benzthiazolyl; 2-benzoxazolyl; 2-benzimidazolyl or 1-benztriazolyl.

Claim 4

A compound of Claim 1 wherein Ar represents substituted phenyl, substituted 1-naphthyl or substituted 4-pyrazolyl.

Claim 5

Compound of Claim 1 wherein Ar is wherein R 1 , R 2 , R 3 , R and R independently represent H, halo, haloalkyl, aryl, substituted aryl, hydroxy, alkoxy, haloalkoxy, aryloxy, substituted aryloxy, heteroaryloxy, substituted heteroaryloxy, amino, alkylamino, dialkylamino, nitro, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, substituted or unsubstituted arylthio, substituted or unsubstituted arylsulfinyl, substituted or unsubstituted arylsulfonyl, cyano, carboxylic acids (and derivatives of carboxylic acids such as esters derived from readily available alcohols and amides derived from ammonia or readily available primary or secondary amines), sulfonic acids (and derivatives of sulfonic acids such as sulfonates derived from readily available alcohols and sulfonamides derived from ammonia or readily available primary or secondary amines), formyl, alkylcarbonyl, haloalkylcarbonyl, arylcarbonyl, substituted arylcarbonyl, oximino, oxime ethers, carbinol (and carbinol derivatives such as ethers and esters derived from readily available alkylating agents and carboxylic acids respectively) and mercaptoalkyl (and derivatives of mercaptoalkyl groups such as thioethers and thioesters derived from readily available alkylating agents and carboxylic acids respectively).

Claim 6

A compound of Claim 1 wherein Ar is wherein R l is H, alkyl or aryl and R 2 and R independently represents H, halo, alkyl, haloalkyl, aryl, substituted aryl, hydroxy, alkoxy, haloalkyloxy, aryloxy, substituted aryloxy, heteroaryloxy, substituted heteroaryloxy, amino, alkylamino, dialkylamino, nitro, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, substituted or unsubstituted arylthio, substituted or unsubstituted arylsulfinyl, substituted or unsubstituted arylsulfonyl, cyano, carboxylic acids (and derivatives of carboxylic acids such as esters derived from readily available alcohols and amides derived from ammonia or readily available primary or secondary amines), sulfonic acids (and derivatives of sulfonic acids such as sulfonates derived from readily available alcohols and sulfonamides derived from ammonia or readily available primary or secondary amines), formyl, alkylcarbonyl, haloalkylcarbonyl, arylcarbonyl, substituted arylcarbonyl, oximino, oxime ethers, carbinols (and carbinol derivatives such as ethers and esters derived from readily available alkylating agents and carboxylic acids respectively) and mercaptoalkyl (and derivatives of mercaptoalkyl groups such as thioethers and thioesters derived from readily available alkylating agents and carboxylic acids respectively).

Claim 7

Compound of Claim 1 wherein Ar is wherein R 1 represents halo (F, Cl, Br, I), -NO 2 , phenyl, -OAr, -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 CC1 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 , -CN, -COOR 7 , -CONH 2 , -CONHR 8 , -CONR 8 (R 9 ), -SO 3 R 8 and -SO 3 CH 2 CF 3 ; R 2 and R 4 represent H, halo, (F, Cl, Br, I), C 1 -C 4 alkyl, COOR 7 and -OR 8 ; R 3 is H; and R 5 represents H, C 1 to C 4 alkyl, halo, (F, Cl, Br, I),NO 2 , CF 3 , -OCF 3 , -OCF 2 CF 2 H, -OCF 2 CCl 2 H, -OCH 2 CF 3 , -SCF3, -SCF2CF2H, -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 , -CN, -COOR 7 , -CONH 2 , -CONHR 8 , -CONR 8 (R 9 ), -SO 3 R 8 , -SO 3 CH 2 CF 3 , -CR 6 R 6 OR 6 and CR 6 R 6 SR 6 , wherein Ar represents substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, R 6 represents H, aryl or C 1 -C 4 alkyl, R represents C 1 -C 6 alkyl, alkenyl, alkynyl, aryl, substituted alkyl or substituted aryl and R 8 and R individually represent C 1 -C 4 alkyl.

Claim 8

A compound of Claim 1 wherein Ar is wherein R 1 represents C 1 -C 4 alkyl, halo (F, Cl, Br, I), -NO 2 , -SR 6 , -SOR 6 , -SO 2 R 6 , -COOR 7 or CF 3 ; R 2 represents H, halo (F, Cl, Br, I), C 1 -C 4 alkyl and COOR 7 and R 5 represents H C 1 -C 4 alkyl, halo (F, Cl, Br, I), -CH 2 -OR 6 , phenyl, NO 2 and COOR 7 wherein R 6 represents C 1 -C 4 alkyl and R 7 represents C 1 -C 4 alkyl, C 1 -C 4 alkenyl, C 1 -C 4 alkynyl, 2-ethoxyethyl and 2-pyridylmethyl.

Claim 9

Compound of Claim 7 wherein X, Y and Z independently represents H, halo (F, Cl, Br, I), C 1 -C 4 alkyl or C 1 -C 4 alkoxy.

Claim 10

Compound of Claim 7 wherein X and Z are methyl and Y is hydrogen.

Claim 11

Compound of Claim 7 wherein X is methyl and Y and Z are hydrogen.

Claim 12

Compound of Claim 7 wherein Y is methyl and X and Z are hydrogen.

Claim 13

Compound of Claim 7 wherein Z-is methyl and X and Y are hydrogen.

Claim 14

Compound of Claim 7 wherein Y-is chloro and X and Z are hydrogen.

Claim 15

The compound of Claim 1 which is 5,7-dimethyl-N-(2-trifluoromethylphenyl)-1,2,4-tria- zolo[1,5-a]pyrimidine-2-sulfonamide, 5,7dimethyl-N--(2,6-difluorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5,7dimethyl-N-(2,6-dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5,7-dimethyl-N-(2-chloro-6-fluorophenyl)-1,2,4-tria- zolo[1,5-a]pyrimidine-2-sulfonamide, 5,7-dimethyl-N--(2-bromo-6-chlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5,7-dimethyl-N-(2-chloro-6--iodophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5,7-dimethyl-N-(2-fluoro-6-methylphenyl)--1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5,7--dimethyl-N-(2-chloro-6-methylphenyl)-1,2,4-triazo- lo[1,5-a]pyrimidine-2-sulfonamide, 5,7-dimethyl-N--(2-bromo-6-methylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5,7-diemthyl-N-(2-methyl-6--nitrophenyl)-1,2,4,-triazolo[1,5-a]pyrimidine-2--sulfonamide, 5,7-dimethyl-N-(2-chloro-6-methoxy- methylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5,7-dimethyl-N-(2-fluoro-6-methoxymethyl- phenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5,7-dimethyl-N-(2-chloro-6-phenylphenyl)--1,2,4-triazolo[1,5-a]pyrimidine -2-sulfonamide, 5,7-dimethyl-N-(2-methyl-6-trifluoromethylphenyl)--1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5,7--dimethyl-N-(2-fluoro-6-trifluoromethylphenyl)-1,2,4--triazolo[1,5-a]pyrimidine-2-sulfonamide, 5,7-dimethyl-N-(2,6-dichloro-3-methylphenyl)-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonamide, 5,7-dimethyl-N-(2,6-di- fluoro-3-methylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5,7-dimethyl-N-(2,3-dimethyl-6--nitrophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5,7-dimethyl-N-(3,6-dimethyl-2-nitrophenyl)--1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5,7--dimethyl-N-(2,3-dichloro-6-methylphenyl)-1,2,4-tria- zolo[1,5-a]pyrimidine-2-sulfonamide, methyl 3-methyl--N-(5,7-dimethyl-l,2,4-triazolo[l,5-a]pyrimidine-2--sulfonyl)anthranilate, ethyl 3-methyl-N-(5,7-dimethyl-l,2,4-triazolo[l,5-a]-pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-methyl-N-(5,7-dimethyl-1,2,4--triazolo[1,5-a]-pyrimidine-2-sulfonyl)anthranilate, 2-ethoxyethyl 3-methyl-N-(5,7-dimethyl-1,2,4-tria- zolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, 2-propen-l-yl 3-methyl-N-(5,7-dimethyl-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonyl)anthranilate, 2-pyridylmethyl 3-methyl-N-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-fluoro-N-(5,7--dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)-anthranilate, ethyl 3-fluoro-N-(5,7-dimethyl-l,2,4--triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-fluor-N-(5,7-dimethyl-1,2,4-triazolo-[l,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-chloro-N-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-chloro-N--(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2--sulfonyl)anthranilate, isopropyl 3-chloro-N-( 5 , 7 --dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-trifluoromethyl-N-(5,7--dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-trifluoromethyl-N-(5,7--dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-trifluoromethyl-N--(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2--sulfonyl)anthranilate, methyl 3,4-dimethyl-N-(5,7--dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3,4-dimethyl-N-(5,7-dimethyl--l,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3,4-dimethyl-N-(5,7-dimethyl-1,2,4--triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3,6-dimethyl-N-(5,7-dimethyl-1,2,4-triazolo-[l,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3,6--dimethyl-N-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3,6-dimethyl--N-(5,7-dimethyl-1,2,4-triazolo[1,5-a]-pyrimidine-2--sulfonyl)anthranilate, methyl 4-chloro-3-methyl-N--(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 4-chloro-3-methyl-N-(5,7--dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)-anthranilate, isopropyl 4-chloro-3-methyl-N-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-amino-2,4-dichloro-N-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, ethyl 3-amino-2,4-dichloro-N-(5,7-dimethyl-1,2,4-tria- zolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, isopropyl 3-amino-2,4-dichloro-N-(5,7-dimethyl-1,2,4-trlazolo-[1,5-a]pyrimidine-2-sulfonyl)benzoate, methyl 3-amino--2-bromo-4-methyl-N-(5,7-dimethyl-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonyl)benzoate, ethyl 3-amino-2--bromo-4-methyl-N-(5,7-dimethyl-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonyl)benzoate, isopropyl 3-amino--2-bromo-4-methyl-N-(5,7-dimethyl-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonyl)benzoate, 5-methyl-N-(2-trifluoromethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine--2-sulfonamide, 5-methyl-N-(2,6-difluorophenyl)-l,2,4--triazolo[1,5-a]pyrimidine-2-sulfonamide, 5-methyl-N--(2,6-dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine--2-sulfonamide, 5-methyl-N-(2-chloro-6-fluorophenyl)--1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5-methyl-N-(2-bromo-6-chlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5-methyl-N-(2-chloro-6-iodophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5-methyl-N-(2-fluoro-6-methylpheny3)-1,2,4-triazolo-[l,5-a]pyrimidine-2-sulfonamide, 5-methyl-N-(2-chloro--6-methylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5-methyl-N-(2-bromo-6-methylphenyl)-l,2,4--triazolo[1,5-a]pyrimidine-2-sulfonamide, 5-methyl-N--(2-methyl-6-nitrophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5-methyl-N-(2-chloro-6-methoxy- methylphenyl)-1,2,4-triazolo[1,S-a]pyrimidine-2-sulfonamide, 5-methyl-N-(2-fluoro-6-methoxymethylphe- nyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5-methyl-N-(2-chloro-6-phenylphenyl)-1,2,4-triazolo-[l,5-a]pyrimidine-2-sulfonamide, 5-methyl-N-(2-methyl--6-trifluoromethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5-methyl-N-(2-fluoro-6-trifluoromethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5-methyl-N-(2,6-dichloro-3-methylphenyl)-1,2,4--triazolo[1,5-a]pyrimidine-2-sulfonamide, 5-methyl-N--(2,6-difluoro-3-methylphenyl)-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonamide, 5-methyl-N-(2,3-dimethyl-6--nitrophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5-methyl-N-(3,6-dimethyl-2-nitrophenyl)--1,2,4-triazolo[1,5-a]pyrimidien-2-sulfonamide, 5-methyl-N-(2,3-dichloro-6-methylphenyl)1,2,4-tria- zolo.[1,5-a]pyrimidine-2-sulfonamide, methyl 3-methyl-

Claim 16

- N -(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-methyl-N-(5-methyl-1,2,4-

Claim 17

- N -(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-methyl-N-(5-methyl-1,2,4-

Claim 18

-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-methyl-N-(5-methyl-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonyl)anthranilate, 2-ethoxyethyl 3-methyl-N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-

Claim 19

-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-methyl-N-(5-methyl-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonyl)anthranilate, 2-ethoxyethyl 3-methyl-N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-

Claim 20

-2-sulfonyl)anthranilate, 2-propen-l-yl 3-methyl-N-

Claim 21

-2-sulfonyl)anthranilate, 2-propen-l-yl 3-methyl-N-

Claim 22

-(5-methyl-1,2,4-triazolo[1,5,-a]pyrimidine-2-sulfonyl)anthranilate, 2-pyridylmethyl 3-methyl-N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-fluoro-N-(5-methyl-1,2,4-triazolo[1,5-

Claim 23

-(5-methyl-1,2,4-triazolo[1,5,-a]pyrimidine-2-sulfonyl)anthranilate, 2-pyridylmethyl 3-methyl-N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-fluoro-N-(5-methyl-1,2,4-triazolo[1,5-

Claim 24

-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-fluoro-

Claim 25

-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-fluoro-

Claim 26

-N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-fluoro-N-(5-methyl-1,2,4-

Claim 27

-N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-fluoro-N-(5-methyl-1,2,4-

Claim 28

-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-chloro-N-(5-methyl-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonyl)anthranilate, ethyl 3-chloro-

Claim 29

-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-chloro-N-(5-methyl-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonyl)anthranilate, ethyl 3-chloro-

Claim 30

-N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-chloro-N-(5-methyl-

Claim 31

-N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-chloro-N-(5-methyl-

Claim 32

-l,2,4-triazolo[l,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-trifluoromethyl-N-(5-methyl-1,2,4-

Claim 33

-l,2,4-triazolo[l,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-trifluoromethyl-N-(5-methyl-1,2,4-

Claim 34

-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-trifluoromethyl-N-(5-methyl-1,2,4-triazolo-[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-trifluoromethyl-N-(5-methyl-1,2,4-triazolo[1,5,-a]-pyrimidine-2-sulfonyl)anthranilate, methyl 3,4-dimethyl-N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-

Claim 35

-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-trifluoromethyl-N-(5-methyl-1,2,4-triazolo-[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-trifluoromethyl-N-(5-methyl-1,2,4-triazolo[1,5,-a]-pyrimidine-2-sulfonyl)anthranilate, methyl 3,4-dimethyl-N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-

Claim 36

-2-sulfonyl)anthranilate, ethyl 3,4-dimethyl-N-(5-

Claim 37

-2-sulfonyl)anthranilate, ethyl 3,4-dimethyl-N-(5-

Claim 38

-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)-anthranilate, isopropyl 3,4-dimethyl-N-(5-methyl--1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3,6-dimethyl-N-(5-methyl-1,2,4-triazo- lo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3,6-dimethyl-N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3,6-dimethyl-N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 4-chloro-3-methyl-N-(5--methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)-anthranilate, ethyl 4-chloro-3-methyl-N-(5-methyl--1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 4-chloro-3-methyl-N-(5-methyl-l,2,4--triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-amino-2,4-dichloro-N-(5-methyl-1,2,4-tria- zolo[l,5-a]pyrimidine-2-sulfonyl)benzoate, ethyl 3-amino-2,4-dichloro-N-(5-methyl-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonyl)benzoate, isopropyl 3-amino--2,4-dichloro-N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, methyl 3-amino-2-bromo-4--methyl-N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine--2-sulfonyl)benzoate, ethyl 3-amino-2-bromo-4-methyl--N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, isopropyl 3-amino-2-bromo-4-methyl-N--(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, 6-methyl-N-(2-trifluoromethylphenyl)--1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2,6-difluorophenyl)-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonamide, 6-methyl-N-(2,6-dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-chloro-6-fluorophenyl)-1,2,4--triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl--N-(2-bromo-6-chlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-chloro-6-iodophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-fluoro-6-methylphenyl)-1,2,4-triazolo-[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-chloro--6-methylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-bromo-6-methylphenyl)-1,2,4--triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N--(2-methyl-6-nitrophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-chloro-6-methoxy- methylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-fluoro-6-methoxymethylphe- nyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-chloro-6-phenylphenyl)-1,2,4-triazolo-[l,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-methyl--6-trifluoromethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-fluoro-6-trifluoromethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2,6-dichloro-3-methylphenyl)-1,2,4--triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N--(2,6-difluoro-3-methylphenyl)-1,2,4-triazolo[1,5,-a]-pyrimidine-2-sulfonamide, 6-methyl-N-(2,3-dimethyl-6--nitrophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(3,6-dimethyl-2-nitrophenyl)-1,2,4--triazolo[l,5-a]pyrimidine-2-sulfonamide, 6-methyl-N--(2,3-dichloro-6-methylphenyl)-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonamide, methyl 3-methyl-N-(6-methyl--1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonyl)anthranilate, ethyl 3-methyl-N-(6-methyl-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-methyl-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, 2-ethoxyethyl 3-meth-. yl-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2--sulfonyl)anthranilate, 2-propen-l-yl 3-methyl-N--(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, 2-pyridylmethyl 3-methyl-N-(6--methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)-anthranilate, methyl 3-fluoro-N-(6-methyl-1,2,4-tria- zolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-fluoro-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine--2-sulfonyl)anthranilate, isopropyl 3-fluoro-N-(6--methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)-anthranilate, methyl 3-chloro-N-(6-methyl-l,2,4-tria- zolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-chloro-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine--2-sulfonyl)anthranilate, isopropyl 3-chloro-N-(6--methyl-1,2,4-triazolo(1,5-a]pyrimidine-2-sulfonyl)-anthranilate, methyl 3-trifluoromethyl-N-(6-methyl--l,2,4-triazolo[l,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-trifluoromethyl-N-(6-methyl-l,2,4-tri- azolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-trifluoromethyl-N-(6-methyl-l,2,4-triazolo-[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3,4-dimethyl-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3,4-dimethyl--N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3,4-dimethyl-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3,6-dimethyl-N-(6-methyl_1,2,4-triazolo-[l,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3,6--dimethyl-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine--2-sulfonyl)anthranilate, isopropyl 3,6-dimethyl-N-(6--methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 4-chloro-3-methyl-N-(6-methyl-1,2,4--triazalo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 4-chloro-3-methyl-N-(6-methyl-1,2,4-triazolo-[l,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 4 -chloro-3-methyl-N-(6-methyl-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonyl)anthranilate, methyl 3-amino--2,4-dichloro-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, ethyl 3-amino-2,4-dichlo- ro-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, isopropyl 3-amino-2,4-dichloro-N-(6--methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)-benzoate, methyl 3-amino-2-bromo-4-methyl-N-(6-methyl--1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, ethyl 3-amino-2-bromo-4-methyl-N-(6-methyl-1,2,4-tri- azolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, isopropyl 3-amino-2-bromo-4-methyl-N-(6-methyl-1,2,4-triazolo-[l,5-a]pyrimidine-2-sulfonyl)benzoate, 7-methyl-N-(2--trifluoromethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2,6-difluorophenyl)--l,2,4-triazolo[l,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2,6-dichlorophenyl)-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonamide, 7-methyl-N-(2-chloro-6--fluorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2-bromo-6-chlorophenyl)-1,2,4--triazolo[1,5-a]-pyrimidine-2-sulfonamide, 7-methyl--N-(2-chloro-6-iodophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2-fluoro-6-methylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2-chloro-6-methylphenyl)-l,2,4-triazolo-[l,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2-bromo--6-methylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2-methyl-6-nitrophenyl)-1,2,4--triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N--(2-chloro-6-methoxymethylphenyl)-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonamide, 7-methyl-N-(2-fluoro-6--methoxymethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine--2-sulfonamide, 7-methyl-N-(2-chloro-6-phenylphenyl)--1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl- N -(2-methyl-6-trifluoromethylphenyl)-1,2,4-triazolo-[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2-fluoro-- 6 -trifluoromethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2,6-dichloro-3-methylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2,6-difluoro-3-methylphenyl)-1,2,4-tria- zolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2,3--dimethyl-6-nitrophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(3,6-dimethyl-2-nitrophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2,3-dichloro-6-methylphenyl)-1,2,4-tria- zolo[1,5-a]pyrimidine-2-sulfonamide, methyl 3-methyl--N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-methyl-N-(7-methyl-l,2,4--triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-methyl-N-(7-methyl-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonyl)anthranilate, 2-ethoxyethyl 3-methyl-N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine--2-sulfonyl)anthranilate, 2-propen-l-yl 3-methyl-N--(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, 2-pyridylmethyl 3-methyl-N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-fluoro-N-(7-methyl-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-fluoro--N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-fluoro-N-(7-methyl-l,2,4--triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-chloro-N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-chloro-N--(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-chloro-N-(7-methyl-- 1 ,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-trifluoromethyl-N-(7-methyl-l,2,4--triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-trifluoromethyl-N-(7-methyl-1,2,4-triazolo-[l,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-trifluoromethyl-N-(7-methyl-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonyl)anthranilate, methyl 3,4-dimethyl-N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine--2-sulfonyl)anthranilate, ethyl 3,4-dimethyl-N-(7--methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)-anthranilate, isopropyl 3,4-dimethyl-N-(7-methyl--1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3,6-dimethyl-N-(7-methyl-1,2,4-tria- zolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3,6-dimethyl-N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3,6-dimethyl--N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 4-chloro-3-methyl-N-(7-methyl--l,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 4-chloro-3-methyl-N-(7-methyl-1,2,4-tria- zolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 4-chloro-3-methyl-N-(7-methyl-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-amino--2,4-dichloro-N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, ethyl 3-amino-2,4-dichloro--N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, isopropyl 3-amino-2,4-dichloro-N-(7--methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)-benzoate, methyl 3-amino-2-bromo-4-methyl-N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, ethyl 3-amino-2-bromo-4-methyl-N-(7-methyl-1,2,4--triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, isopropyl 3-amino-2-bromo-4-methyl-N-(7-methyl-1,2,4-triazo- lo[l,5-a]pyrimidine-2-sulfonyl)benzoate, 6-chloro-N--(2,6-dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine--2-sulfonamide, 6-chloro-N-(2,6-difluorophenyl)-1,2,4--triazolo[l,5-a]pyrimidine-2-sulfonamide, 6-chloro-N--(2-chloro-6-methylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-chloro-N-(2-methyl-6-nitrophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6 -chloro-N-(2,6-dichloro-3-methylphenyl)-l,2,4-tria- zolo[1,5-a]pyrimidine-2-sulfonamide, 6-chloro-N-(2,3--dimethyl-6-nitrophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, methyl 3-methyl-N-(6-chloro-l,2,4--triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-fluoro-N-(6-chloro-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonyl)anthranilate, 5-methoxy-N-(2,6--dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2--sulfonamide, 5,7-dimethyl-N-(2-chloro-l-napthyl)--1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5-methyl-N-(2-chloro-1-napthyl)1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonamide, or 5-methyl-N-(1,3-dimethyl-5-trifluoromethyl-4-pyrazolyl)1,2,4-triazo- lo[1,5-a]pyrimidine-2-sulfonamide.

Claim 39

-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)-anthranilate, isopropyl 3,4-dimethyl-N-(5-methyl--1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3,6-dimethyl-N-(5-methyl-1,2,4-triazo- lo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3,6-dimethyl-N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3,6-dimethyl-N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 4-chloro-3-methyl-N-(5--methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)-anthranilate, ethyl 4-chloro-3-methyl-N-(5-methyl--1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 4-chloro-3-methyl-N-(5-methyl-l,2,4--triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-amino-2,4-dichloro-N-(5-methyl-1,2,4-tria- zolo[l,5-a]pyrimidine-2-sulfonyl)benzoate, ethyl 3-amino-2,4-dichloro-N-(5-methyl-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonyl)benzoate, isopropyl 3-amino--2,4-dichloro-N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, methyl 3-amino-2-bromo-4--methyl-N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine--2-sulfonyl)benzoate, ethyl 3-amino-2-bromo-4-methyl--N-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, isopropyl 3-amino-2-bromo-4-methyl-N--(5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, 6-methyl-N-(2-trifluoromethylphenyl)--1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2,6-difluorophenyl)-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonamide, 6-methyl-N-(2,6-dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-chloro-6-fluorophenyl)-1,2,4--triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl--N-(2-bromo-6-chlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-chloro-6-iodophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-fluoro-6-methylphenyl)-1,2,4-triazolo-[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-chloro--6-methylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-bromo-6-methylphenyl)-1,2,4--triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N--(2-methyl-6-nitrophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-chloro-6-methoxy- methylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-fluoro-6-methoxymethylphe- nyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-chloro-6-phenylphenyl)-1,2,4-triazolo-[l,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-methyl--6-trifluoromethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2-fluoro-6-trifluoromethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(2,6-dichloro-3-methylphenyl)-1,2,4--triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N--(2,6-difluoro-3-methylphenyl)-1,2,4-triazolo[1,5,-a]-pyrimidine-2-sulfonamide, 6-methyl-N-(2,3-dimethyl-6--nitrophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-methyl-N-(3,6-dimethyl-2-nitrophenyl)-1,2,4--triazolo[l,5-a]pyrimidine-2-sulfonamide, 6-methyl-N--(2,3-dichloro-6-methylphenyl)-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonamide, methyl 3-methyl-N-(6-methyl--1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonyl)anthranilate, ethyl 3-methyl-N-(6-methyl-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-methyl-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, 2-ethoxyethyl 3-meth-. yl-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2--sulfonyl)anthranilate, 2-propen-l-yl 3-methyl-N--(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, 2-pyridylmethyl 3-methyl-N-(6--methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)-anthranilate, methyl 3-fluoro-N-(6-methyl-1,2,4-tria- zolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-fluoro-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine--2-sulfonyl)anthranilate, isopropyl 3-fluoro-N-(6--methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)-anthranilate, methyl 3-chloro-N-(6-methyl-l,2,4-tria- zolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-chloro-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine--2-sulfonyl)anthranilate, isopropyl 3-chloro-N-(6--methyl-1,2,4-triazolo(1,5-a]pyrimidine-2-sulfonyl)-anthranilate, methyl 3-trifluoromethyl-N-(6-methyl--l,2,4-triazolo[l,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-trifluoromethyl-N-(6-methyl-l,2,4-tri- azolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-trifluoromethyl-N-(6-methyl-l,2,4-triazolo-[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3,4-dimethyl-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3,4-dimethyl--N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3,4-dimethyl-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3,6-dimethyl-N-(6-methyl_1,2,4-triazolo-[l,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3,6--dimethyl-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine--2-sulfonyl)anthranilate, isopropyl 3,6-dimethyl-N-(6--methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 4-chloro-3-methyl-N-(6-methyl-1,2,4--triazalo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 4-chloro-3-methyl-N-(6-methyl-1,2,4-triazolo-[l,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 4 -chloro-3-methyl-N-(6-methyl-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonyl)anthranilate, methyl 3-amino--2,4-dichloro-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, ethyl 3-amino-2,4-dichlo- ro-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, isopropyl 3-amino-2,4-dichloro-N-(6--methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)-benzoate, methyl 3-amino-2-bromo-4-methyl-N-(6-methyl--1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, ethyl 3-amino-2-bromo-4-methyl-N-(6-methyl-1,2,4-tri- azolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, isopropyl 3-amino-2-bromo-4-methyl-N-(6-methyl-1,2,4-triazolo-[l,5-a]pyrimidine-2-sulfonyl)benzoate, 7-methyl-N-(2--trifluoromethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2,6-difluorophenyl)--l,2,4-triazolo[l,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2,6-dichlorophenyl)-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonamide, 7-methyl-N-(2-chloro-6--fluorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2-bromo-6-chlorophenyl)-1,2,4--triazolo[1,5-a]-pyrimidine-2-sulfonamide, 7-methyl--N-(2-chloro-6-iodophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2-fluoro-6-methylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2-chloro-6-methylphenyl)-l,2,4-triazolo-[l,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2-bromo--6-methylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2-methyl-6-nitrophenyl)-1,2,4--triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N--(2-chloro-6-methoxymethylphenyl)-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonamide, 7-methyl-N-(2-fluoro-6--methoxymethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine--2-sulfonamide, 7-methyl-N-(2-chloro-6-phenylphenyl)--1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl- N -(2-methyl-6-trifluoromethylphenyl)-1,2,4-triazolo-[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2-fluoro-- 6 -trifluoromethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2,6-dichloro-3-methylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2,6-difluoro-3-methylphenyl)-1,2,4-tria- zolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2,3--dimethyl-6-nitrophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(3,6-dimethyl-2-nitrophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 7-methyl-N-(2,3-dichloro-6-methylphenyl)-1,2,4-tria- zolo[1,5-a]pyrimidine-2-sulfonamide, methyl 3-methyl--N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-methyl-N-(7-methyl-l,2,4--triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-methyl-N-(7-methyl-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonyl)anthranilate, 2-ethoxyethyl 3-methyl-N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine--2-sulfonyl)anthranilate, 2-propen-l-yl 3-methyl-N--(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, 2-pyridylmethyl 3-methyl-N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-fluoro-N-(7-methyl-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-fluoro--N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-fluoro-N-(7-methyl-l,2,4--triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-chloro-N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-chloro-N--(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-chloro-N-(7-methyl-- 1 ,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-trifluoromethyl-N-(7-methyl-l,2,4--triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3-trifluoromethyl-N-(7-methyl-1,2,4-triazolo-[l,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3-trifluoromethyl-N-(7-methyl-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonyl)anthranilate, methyl 3,4-dimethyl-N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine--2-sulfonyl)anthranilate, ethyl 3,4-dimethyl-N-(7--methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)-anthranilate, isopropyl 3,4-dimethyl-N-(7-methyl--1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3,6-dimethyl-N-(7-methyl-1,2,4-tria- zolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 3,6-dimethyl-N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 3,6-dimethyl--N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 4-chloro-3-methyl-N-(7-methyl--l,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, ethyl 4-chloro-3-methyl-N-(7-methyl-1,2,4-tria- zolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, isopropyl 4-chloro-3-methyl-N-(7-methyl-1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-amino--2,4-dichloro-N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, ethyl 3-amino-2,4-dichloro--N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, isopropyl 3-amino-2,4-dichloro-N-(7--methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)-benzoate, methyl 3-amino-2-bromo-4-methyl-N-(7-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, ethyl 3-amino-2-bromo-4-methyl-N-(7-methyl-1,2,4--triazolo[1,5-a]pyrimidine-2-sulfonyl)benzoate, isopropyl 3-amino-2-bromo-4-methyl-N-(7-methyl-1,2,4-triazo- lo[l,5-a]pyrimidine-2-sulfonyl)benzoate, 6-chloro-N--(2,6-dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine--2-sulfonamide, 6-chloro-N-(2,6-difluorophenyl)-1,2,4--triazolo[l,5-a]pyrimidine-2-sulfonamide, 6-chloro-N--(2-chloro-6-methylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6-chloro-N-(2-methyl-6-nitrophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 6 -chloro-N-(2,6-dichloro-3-methylphenyl)-l,2,4-tria- zolo[1,5-a]pyrimidine-2-sulfonamide, 6-chloro-N-(2,3--dimethyl-6-nitrophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, methyl 3-methyl-N-(6-chloro-l,2,4--triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate, methyl 3-fluoro-N-(6-chloro-1,2,4-triazolo[1,5-a]-pyrimidine-2-sulfonyl)anthranilate, 5-methoxy-N-(2,6--dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2--sulfonamide, 5,7-dimethyl-N-(2-chloro-l-napthyl)--1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5-methyl-N-(2-chloro-1-napthyl)1,2,4-triazolo[1,5--a]pyrimidine-2-sulfonamide, or 5-methyl-N-(1,3-dimethyl-5-trifluoromethyl-4-pyrazolyl)1,2,4-triazo- lo[1,5-a]pyrimidine-2-sulfonamide.

Claim 40

A compound of Claim 1 wherein V is R and R represents alkyl, alkenyl, alkynyl, arylalkyl, substituted arylalkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, dialkylaminocarbonyl, alkylsulfonyl, arylsulfonyl, alkylthiocarbonyl or arylthiocarbonyl.

Claim 41

A compound of Claim 15 wherein Ar is as defined in Claim 2.

Claim 42

A compound of Claim 15 wherein Ar is as defined in Claim 3.

Claim 43

A compound of Claim 15 wherein Ar is as defined in Claim 4.

Claim 44

A compound of Claim 15 wherein Ar is as defined in Claim 5.

Claim 45

A compound of Claim 15 wherein Ar is as defined in Claim 6.

Claim 46

A compound of Claim 15 wherein Ar is as defined in Claim 7.

Claim 47

A compound of 21 wherein X, Y and Z are as defined in Claim 8.

Claim 48

A compound of Claim 22 wherein R represents C 1 -C 4 alkyl, C 1 -C 4 alkenyl, C 1 -C 4 alkynyl, benzyl, substituted benzyl, -COR 1 , -COOR 1 , -CONR 1 R 2 , -SO 2 R 1 or -COSR 1 wherein R 1 and R 2 independently represent C 1 -C 4 alkyl, phenyl or substituted phenyl.

Claim 49

A compound of Claim 22 wherein R represents -COR 1 , -COOR 1 or -CONR 1 R 2 wherein R 1 and R 2 independently represent C 1 -C 4 alkyl or phenyl.

Claim 50

A compound of Claim 24 wherein X, Y and Z are as defined in Claim 9.

Claim 51

A compound of Claim 25 wherein X, Y and Z are as defined in Claim 10.

Claim 52

A compound of Claim 25 wherein X, Y and Z are as defined in Claim 11.

Claim 53

A compound of Claim 25 wherein X, Y and Z are as defined in Claim 12.

Claim 54

The compound of Claim 15 which is 5,7-dimethyl-N-acetyl-N-(2,6-dichlorphenyl)-1,2,4-tri- azolo[1,5-a]pyrimidine-2-sulfonamide, 5-methyl-N-acetyl-N-(2,6-dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5-methyl-N-isobutyryl-N-(2,6--dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2--sulfonamide or 5-methyl-N-ethoxycarbonyl-N-(2,6--dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine--2-sulfonamide.

Claim 55

A compound having the formula: wherein Ar, X, Y and Z are as defined in Claim 1.

Claim 56

A compound of Claim 30 wherein Ar is as defined in Claim 2.

Claim 57

A compound of Claim 30 wherein Ar is as defined in Claim 3.

Claim 58

A compound of Claim 30 wherein Ar is as defined in Claim 4.

Claim 59

A compound of Claim 30 wherein Ar is as defined in Claim 5.

Claim 60

A compound of Claim 30 wherein Ar is as defined in Claim 6.

Claim 61

A compound of Claim 30 wherein Ar is as defined in Claim 7.

Claim 62

A compound of Claim 36 wherein X, Y and Z independently represent H, C l -C 4 alkyl and C 1 -C 4 alkoxy.

Claim 63

A compound of Claim 36 wherein X and Z are methyl and Y is hydrogen.

Claim 64

A compound of Claim 36 wherein X is methyl and Y and Z are hydrogen.

Claim 65

A compound of Claim 36 wherein Y is methyl and X and Z are hydrogen.

Claim 66

A compound of Claim 36 wherein Z is methyl and X and Y are hydrogen.

Claim 67

The compound of Claim 30 which is 5,7-dimethyl-N-(2,6-dichlorophenyl)-4,5,6,7-tetrahy- dro-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide, 5-methyl-N-(2,6-dichlorophenyl)-4,5,6,7-tetrahydro--1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide or 5,7-dimethyl-N-(2-trifluoromethylphenyl)-4,5,6,7--tetrahydro-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide.

Claim 68

A composition comprising an inert carrier in admixture with a herbicidally effective amount of a compound or salt of a compound of Claims 1 through 42.

Claim 70

Method for suppressing the nitrification of ammonium nitrogen in growth media which comprises impregnating said growth media with an effective amount of a compound of Claims 1 through 42.

Claim 71

Method for inhibiting the bolting of sugarbeets which comprises the application of an effective amount of a compound of Claims 1 through 42.

Claim 72

A compound having the formula wherein X, Y and Z independently represent hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, halogen, aryl, substituted aryl or two substituents are joined together in a cyclic structure.

Claim 73

A compound having the formula wherein X, Y and Z independently represent hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, halogen, aryl, substituted aryl or two substituents are joined together in a cyclic structure.

Claim 74

A compound of Claim 47 wherein X, Y and Z independently represent hydrogen, halo, C 1 -C 4 alkyl or C l -C 4 alkoxy.

Claim 75

A compound of Claim 47 wherein X and Z are methyl and Y is hydrogen.

Claim 76

A compound of Claim 47 wherein X is methyl and Y and Z are hydrogen.

Claim 77

A compound of Claim 47 wherein Y is methyl and X and Z are hydrogen.

Claim 78

A compound of Claim 47 wherein Z is methyl and X and Y are hydrogen.

Claim 79

A compound of Claim 47 wherein Y is chloro and X and Z are hydrogen.

Claim 80

A compound having the formula wherein X, Y and Z independently represent hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, halogen, aryl, substituted aryl or two substituents are joined together in a cyclic structure; and R represents hydrogen, benzyl or substituted benzyl.

Claim 81

A compound having the formula wherein X, Y and Z independently represent hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, halogen, aryl, substituted aryl or two substituents are joined together in a cyclic structure; and R represents hydrogen, benzyl or substituted benzyl.

Claim 82

A compound of Claim 54 wherein X, Y and Z independently represent hydrogen, halo, C l -C 4 alkyl or C 1 -C 4 alkoxy, and R represents H or benzyl.

Claim 83

A compound of Claim 54 wherein X and Z are methyl, and Y and R are hydrogen.

Claim 84

A compound of Claim 54 wherein X and Z are methyl, Y is hydrogen and R is benzyl.

Claim 85

A compound of Claim 54 wherein X is methyl, and Y, Z and R are hydrogen.

Claim 86

A compound of Claim 54 wherein X is methyl, Y and Z are hydrogen, and R is benzyl.

Claim 87

A compound of Claim 54 wherein Y is methyl, and X, Z and R are hydrogen.

Claim 88

A compound of Claim 54 wherein Y is methyl, X and Z are hydrogen, and R is benzyl.

Claim 89

A compound of Claim 54 wherein Z is methyl, and X, Y and R are hydrogen.

Claim 90

A compound of Claim 54 wherein Z is methyl, X and Y are hydrogen, and R is benzyl.

Claim 91

A compound of Claim 54 wherein Y is chloro, and X, Z and R are hydrogen.

Claim 92

A compound of Claim 54 wherein Y is chloro, X and Z are hydrogen, and R is benzyl.

Claim 93

A method of preparing a compound of Claim 47 wherein a compound of Claim 54 is treated with chlorine in an aqueous acidic media.

Claim 94

Method of preparing a compound of Claim 1 wherein a compound of formula ArNH 2 wherein Ar represents a substituted or unsubstituted aromatic or heteroaromatic ring system is reacted with a compound of Claim 47.

Claim 95

A compound useful in the preparation of a compound Of Claim 4 which is methyl 3-amino-2,4-dichlorobenzoate, methyl 3-amino-2-bromo-4-methylbenzoate, methyl 4-chloro-3-methyl-I-anthranilate, 3-amino--2,4-dichlorobenzotrifluoride, 4-bromo-2,3-dichloro-6--methyl aniline, 2,3-dichloro-6-methyl aniline, 2-chloro-6-methoxymethyl aniline, 2-acetoxy-methyl-6-chloro aniline, 2-benzyloxymethyl-6-chloro aniline, 2-(2-chloro-4-trifluoromethylphenoxy)aniline, 2-(3-chloro-5-trifluoromethyl-2-pyridyloxy)aniline, 2-(2-chloro-4-tri- fluoromethylphenoxy)-6-fluoro aniline, 2-fluoro-6--methylaniline or 2-fluoro-6-methylthio aniline.