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US 5,494,887 AGranted
Ring annulated 5-alkoxy-n-aryl[1,2,4]triazolo[1,5-C]-pyrimidine-2-sulfonamide herbicides
AssigneeDowElanco
InventorsTimothy C. Johnson, Walter Reifschneider, John C. Van Heertum, Mark J. Costales, Kim E. Arndt
Life of this patent
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Abstract
Substituted ring annulated 5-alkoxy-N-aryl-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide compounds, such as N-(2,6-dichlorophenyl)-5-methoxycyclopenteno[d]-[1,2,4]triazolo[1,5-c]pyri midine-2-sulfonamide, were prepared by condensation of an appropriate 2-chloro-sulfonyl-5-alkoxy[1,2,4]triazolo[1,5-c]pyrimidine compound, such as 2-chlorosulfonyl-5-methoxycyclopenteno[d][1,2,4]triazolo[1,5-c]pyrimidine, with a substituted arylamine compound, such as 2,6-dichloroaniline, and found to possess herbicidal utility.
Claims22
A 5-alkoxy-N-aryl[1,2,4]triazolo[1,5-c]-pyrimidine-2-sulfonamide compound of the formula:
- ##STR12## wherein R represents CH.sub.2 CF.sub.3 or (C.sub.1 -C.sub.3)alkyl optionally monosubstituted with F, Cl, or OCH.sub.3 ;
- X and Y together represent a biradical fragment of the formula --Z--CH.dbd.CH--, --CH.dbd.CH--Z--, --Z--CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --Z--, --(CH.sub.2).sub.3 --, --CH.dbd.CH--CH.dbd.CH--, or --N.dbd.CH--CH.dbd.CH-- each optionally substituted with CH.sub.3 ;
- Z represents O, or S;
- V represents H, COR', CO.sub.2 R", or CONR"'2;
- Ar represents an aromatic moiety one of the formulas:
- ##STR13## A represents F, Cl, Br, CO.sub.2 R", CONR'".sub.2, (C.sub.1 -C.sub.2)haloalkyl, NO.sub.2, CN, SOR', or SO.sub.2 R';
- B represents H, CH.sub.3, C.sub.2 H.sub.5, F, Cl, Br, CN, OR', SR', NR"'.sub.2, phenyl, or phenoxy, each phenyl and phenoxy optionally possessing 1 to 3 substituents selected from the group consisting of F, Cl, Br, CN, CF.sub.3, NO.sub.2, and CH.sub.3 ;
- D and J each independently represents H or CH.sub.3 with the proviso that at least one of D and J represents H;
- A' and B' each independently represents H, R', OR', S(O).sub.n R', F, Cl, Br, I, CN, NO.sub.2, C.sub.6 H.sub.5, CO.sub.2 R", or CONR'".sub.2 with the proviso that not more than one of A' and B' represents H;
- D' represents H, F, Cl, Br, I, CF.sub.3, or CH.sub.3 ;
- A" represents F, Cl, Br, I, CF.sub.3, SCF.sub.3, CN, CO.sub.2 R", or CONR'".sub.2 and is located in the 4-position when the point of attachment is the 3- or 5-position and represents F, Cl, Br, I, CF.sub.3, or CH.sub.3 and is located in the 3- and/or 5-position when the point of attachment is the 4-position;
- T represents H or F;
- n represents 0, 1, or 2;
- R' represents (C.sub.1 -C.sub.4)alkyl optionally singly to completely substituted with fluorine;
- R" represents (C.sub.1 -C.sub.4)alkyl, (C.sub.3 -C.sub.4)alkenyl, or (C.sub.3 -C.sub.4)alkynyl;
- R"' represents H or (C.sub.1 -C.sub.4)alkyl;
- and
- when V represents H, the agriculturally acceptable salts thereof.
15 more elements
An herbicidal composition comprising an herbicidally effective amount of a 5-alkoxy-N-aryl[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide compound of the formula:
- ##STR17## wherein R represents CH.sub.2 CF.sub.3 or (C.sub.1 -C.sub.3) alkyl optionally monosubstituted with F, Cl, or OCH.sub.3 ;
- X and Y together represent a biradical fragment of the formula --Z--CH.dbd.CH--, --CH.dbd.CH--Z--, --Z--CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --Z--, --(CH.sub.2).sub.3 --, --CH.dbd.CH--CH.dbd.CH--, or --N.dbd.CH--CH.dbd.CH-- each optionally substituted with CH.sub.3 ;
- Z represents O, or S;
- V represents H, COR', CO.sub.2 R", or CONR"'.sub.2 ;
- Ar represents an aromatic moiety one of the formulas:
- ##STR18## A represents F, Cl, Br, CO.sub.2 R", CONR'".sub.2, (C.sub.1 -C.sub.2)haloalkyl, NO.sub.2, CN, SOR', or SO.sub.2 R';
- B represents H, CH.sub.3, C.sub.2 H.sub.5, F, Cl, Br, CN, OR', SR', NR"'.sub.2, phenyl, or phenoxy, each phenyl and phenoxy optionally possessing 1 to 3 substituents selected from the group consisting of F, Cl, Br, CN, CF.sub.3, NO.sub.2, and CH.sub.3 ;
- D and J each independently represents H or CH.sub.3 with the proviso that at least one of D and J represents H;
- A' and B' each independently represents H, R', OR', S(O).sub.n R', F, Cl, Br, I, CN, NO.sub.2, C.sub.6 H.sub.5, CO.sub.2 R", or CONR'".sub.2 with the proviso that not more than one of A' and B' represents H;
- D' represents H, F, Cl, Br, I, CF.sub.3, or CH.sub.3 ;
- A" represents F, Cl, Br, I, CF.sub.3, SCF.sub.3, CN, CO.sub.2 R", or CONR'".sub.2 and is located in the 4-position when the point of attachment is the 3- or 5-position and represents F, Cl, Br, I, CF.sub.3, or CH.sub.3 and is located in the 3- and/or 5-position when the point of attachment is the 4-position;
- T represents H or F;
- n represents 0, 1, or 2;
- R' represents (C.sub.1 -C.sub.4)alkyl optionally singly to completely substituted with fluorine;
- R" represents (C.sub.1 -C.sub.4)alkyl, (C.sub.3 -C.sub.4)alkenyl, or (C.sub.3 -C.sub.4)alkynyl;
- R"' represents H or (C.sub.1 -C.sub.4)alkyl;
- and
- when V represents H, the agriculturally acceptable salts thereof
- in admixture with an agriculturally acceptable adjuvant or carrier.
16 more elements
A method of controlling undesirable vegetation which comprises applying to said vegetation or to the locus thereof an herbicidally effective amount of a 5-alkoxy-N-aryl[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide compound of the formula:
- ##STR22## wherein R represents CH.sub.2 CF.sub.3 or (C.sub.1 -C.sub.3) alkyl optionally monosubstituted with F, Cl, or OCH.sub.3 ;
- X and Y together represent a biradical fragment of the formula --Z--CH.dbd.CH--, --CH.dbd.CH--Z--, --Z--CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --Z--, --(CH.sub.2).sub.3 --, --CH.dbd.CH--CH.dbd.CH--, or --N.dbd.CH--CH.dbd.CH-- each optionally substituted with CH.sub.3 ;
- Z represents O, or S;
- V represents H, COR', CO.sub.2 R", or CONR"'.sub.2 ;
- Ar represents an aromatic moiety one of the formulas:
- ##STR23## A represents F, Cl, Br, CO.sub.2 R", CONR'".sub.2, (C.sub.1 -C.sub.2)haloalkyl, NO.sub.2, CN, SOR', or SO.sub.2 R';
- B represents H, CH.sub.3, C.sub.2 H.sub.5, F, Cl, Br, CN, OR', SR', NR"'.sub.2, phenyl, or phenoxy, each phenyl and phenoxy optionally possessing 1 to 3 substituents selected from the group consisting of F, Cl, Br, CN, CF.sub.3, NO.sub.2, and CH.sub.3 ;
- D and J each independently represents H or CH.sub.3 with the proviso that at least one of D and J represents H;
- A' and B' each independently represents H, R', OR', S(O).sub.n R', F, Cl, Br, I, CN, NO.sub.2, C.sub.6 H.sub.5, CO.sub.2 R", or CONR'".sub.2 with the proviso that not more than one of A' and B' represents H;
- D' represents H, F, Cl, Br, I, CF.sub.3, or CH.sub.3 ;
- A" represents F, Cl, Br, I, CF.sub.3, SCF.sub.3, CN, CO.sub.2 R", or CONR'".sub.2 and is located in the 4-position when the point of attachment is the 3- or 5-position and represents F, Cl, Br, I, CF.sub.3, or CH.sub.3 and is located in the 3- and/or 5-position when the point of attachment is the 4-position;
- T represents H or F;
- n represents 0, 1, or 2;
- R' represents (C.sub.1 -C.sub.4)alkyl optionally singly to completely substituted with fluorine;
- R" represents (C.sub.1 -C.sub.4)alkyl, (C.sub.3 -C.sub.4) alkenyl, or (C.sub.3 -C.sub.4) alkynyl;
- R"' represents H or (C.sub.1 -C.sub.4)alkyl;
- and
- when V represents H, the agriculturally acceptable salts thereof.
15 more elements
A chlorosulfonyl compound of the formula:
- ##STR27## wherein R represents Cl, CH.sub.2 CF.sub.3 or (C.sub.1 -C.sub.3)alkyl optionally monosubstituted with F, Cl, or OCH.sub.3 ;
- and
- X and Y together represent the biradical --CH.dbd.CH--S-- or --(CH.sub.2).sub.3 --.
Dependencies are inferred from the claim text.