N-[1,2,4]triazoloazinyl) benzenesulfonamide and...

Details N-[1,2,4]triazoloazinyl) benzenesulfonamide and... N-[1,2,4]triazoloazinyl) benzenesulfonamide and...

2000-03-16

2001-10-16

Rotman, Alan L. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Sulfur halides

C562S825000, C562S826000, C562S827000

Reexamination Certificate

active

06303814

ABSTRACT:

BACKGROUND OF THE INVENTION
The present invention relates to substituted benzenesulfonamide and pyridinesulfonamide compounds, to herbicidal compositions containing the compounds, and to the utility of the compounds for the control of unwanted vegetation.
The control of unwanted vegetation by means of chemical agents, i.e., herbicides, is an important aspect of modern agriculture and land management. While many chemicals that are useful for the control of unwanted vegetation are known, new compounds that are more effective generally, are more effective for specific plant species, are less damaging to desirable vegetation, are safer to man or the environment, are less expensive to use, or have other advantageous attributes are desirable.
Many substituted benzenesulfonamide compounds are known and certain of them are known to possess herbicidal activity. For example, certain N-([1,2,4]triazolo[1,5-a]pyrimidin-2-yl)benzenesulfonamide compounds and their herbicidal utility were disclosed in U.S. Pat. No. 4,638,075 and certain N-([1,2,4]triazolo[1,3,5]triazin-2-yl)benzenesulfonamide compounds were disclosed in U.S. Pat. No. 4,685,958. Certain N-phenyl arylsulfonamide compounds are also known and are known to possess herbicidal activity. For example, certain N-(substituted phenyl)[1,2,4]triazolo[1,5-c]pyrimidin-2-sulfonamide compounds were disclosed in U.S. Pat. No. 5,163,995 and certain N-(substituted phenyl)[1,2,4]triazolo[1,5-a]pyridin-2-sulfonamide compounds were disclosed in U.S. Pat. No. 5,571,775, issued Nov. 5, 1996.
SUMMARY OF THE INVENTION
It has now been found that a class of novel N-(triazoloazinyl)arylsulfonamide compounds comprising N-([1,2,4]triazolo[1,5-c]pyrimidin-2-yl)benzenesulfonamide, N-([1,2,4]triazolo[1,5-c]pyrimidin-2-yl)pyridinesulfonamide, N-([1,2,4]triazolo[1,5-a]pyridin-2-yl) benzenesulfonamide, and N-([1,2,4)triazolo[1,5-a]pyridin-2-yl)pyridinesulfonamide compounds are potent herbicides for the control of unwanted vegetation by either preemergence or postemergence application. Many of the compounds have desirable selectivity to valuable crops and have favorable toxicological and environmental attributes.
The invention includes N-(triazoloazinyl)arylsulfonamide compounds of Formula I:
wherein
X represents N or C—Y;
W represents O(C
1
-C
3
alkyl), Cl, Br, F, or H;
Y represents H, OCH
3
, F, Cl, Br, I, or CH
3
optionally substituted with up to three fluorine atoms;
Z represents O(C
1
-C
3
alkyl), H, F, Cl, Br, I, S(C
1
-C
3
alkyl), or CH
3
optionally substituted with up to three fluorine atoms; with the proviso that at least one of W and Z represents O(C
1
-C
3
alkyl);
Q represents C—H or N;
A represents F, Cl, Br, or I, or CO
2
(C
1
-C
4
alkyl) or represents C
1
-C
3
alkyl, O(C
1
-C
4
alkyl), O(C
3
-C
4
alkenyl), O(C
3
-C
4
alkynyl), or S(C
1-C
3 alkyl) each optionally substituted with one O(C
1
-C
3
alkyl), S(C
1
-C
3
alkyl), chloro, bromo, or cyano substituent or with up to the maximum possible number of fluorine atoms, or represents a 2-methyl-1,3-dioxolan-2-yl moiety, and, when Q represents N, H;
B represents H, F, Cl, Br, I, NO
2
, CN, CO
2
(C
1
-C
4
alkyl), NH(C
1
-C
3
alkyl), or N(C
1
-C
3
alkyl)
2
or represents O(C
1
-C
4
alkyl), O(C
3
-C
4
alkenyl), O(C
3
-C
4
alkynyl), C
1
-C
3
alkyl, S(C
1
-C
3
alkyl), SO(C
1
-C
3
alkyl), SO
2
(C
1
-C
3
alkyl), S(C
3
-C
4
alkenyl), SO(C
3
-C
4
alkenyl), SO
2
(C
3
-C
4
alkenyl), S(C
3
-C
4
alkynyl), SO(C
3
-C
4
alkynyl), or SO
2
(C
3
-C
4
alkynyl) each optionally substituted with one O(C
2
-Calkyl), S(C
2
-Calkyl), chloro, bromo, or cyano substituent or with up to the maximum possible number of fluorine atoms; with the proviso that A and B do not simultaneously represent H;
D represents H, F, Cl, Br, I, C
1
-C
3
alkyl, OCH
3
, OC
2
H
5
, CH
2
F, CHF
2
, or CF
3
; or B and D together represent a fragment of the formula O—CH
2
—O, optionally substituted with one or two F or CH
3
;
T represents H, SO
2
R, C(O)R, C(O)OR, C(O)NR′
2
, or CH
2
CH
2
C(O)OR;
R represents C
1
-C
4
alkyl, C
3
-C
4
alkenyl, or C
3
-C
4
alkynyl each optionally possessing up to two chloro, bromo, O(C
1
-C
4
)alkyl, or phenyl substituents and up to the maximum possible number of fluoro substituents; and
R′ represents H, C
1
-C
4
alkyl, C
3
-C
4
alkenyl, or C
3
-C
4
alkynyl;
and, when T represents H, the agriculturally acceptable salts thereof.
Compounds wherein X represents each of N and C—H and compounds wherein Q represents each of N and C—H are among the preferred compounds of the invention. Many of the preferred compounds of the invention possess a methoxy substituent in the 5-position (W) and a methoxy or halogen substituent in the 8-position (Z) of the triazoloazine ring. Some of the preferred compounds further possess an ortho methoxy substituent (A or B) in combination with a variety of substituents in the other ortho postiton (A or B) and hydrogen in the meta position; an ortho methoxy substituent (A) in combination with hydrogen or a meta methyl or chloro substituent (D) and no substituent in the other ortho position (B); or an ortho trifluoromethyl substituent (B) in combination with a variety of substituents in the other ortho postiton (A) and hydrogen in the meta position.
The invention further includes compositions containing herbicidal amounts of compounds of Formula I in combination with one or more agriculturally acceptable adjuvants or carriers and the use of the compounds of Formula I as herbicides. The use of suitable compounds of the invention to achieve either total vegetation control or the selective control of weeds in wheat, rice and oil-seed rape crops is generally preferred. Both grassy and broadleaf weeds can be controlled. Post-emergence application of the compounds to undesirable vegetation is generally preferred.
DETAILED DESCRIPTION OF THE INVENTION
The N-(triazoloazinyl)arylsulfonamide compounds of the invention can generally be described as substituted N-([1,2,4]triazolo[1,5-c]pyrimidin-2-yl)benzenesulfonamide, N-([1,2,4]triazolo[1,5-c]pyrimidin-2-yl)pyridine-3-sulfonamide, N-([1,2,4]triazolo[1,5-a]pyridin-2-yl)benzenesulfonamide, and N-([1,2,4]triazolo[1,5-a]pyridin-2-yl)pyridine-3-sulfonamide compounds. They can be characterized as substituted benzenesulfonamide and pyridine-3-sulfonamide compounds possessing, on the amide nitrogen atom, a substituted [1,2,4]triazolo[1,5-c]pyrimidin-2-yl or substituted [1,2,4]triazolo[1,5-a]pyridin-2-yl moiety.
The herbicidal compounds of the invention are N-(triazoloazinyl)arylsulfonamide compounds of generic Formula I:
Such compounds in which X represents N contain a substituted N-([1,2,4]triazolo[1,5-c]pyrimidin-2-yl) moiety and those in which X represents C—Y contain a substituted N-([1,2,4]triazolo[1,5-a]pyridin-2-yl) moiety. Compounds in which Q represents N are pyridinesulfonamide compounds and compounds in which Q represents C—H are benzenesulfonamide compounds. The compounds are further characterized by possessing a C
1
-C
3
alkoxy substituent in one or both of the 5- and 8-positions (W and Z, respectively) of the triazoloazine ring and by possessing at least one ortho substituent (A) on the phenyl or pyridine ring.
The compounds of the invention include compounds of Formula I wherein X represents N or C—Y (wherein Y represents hydrogen, a halogen, methoxy, or methyl optionally substituted with up to three fluorine atoms). Compounds wherein X represents N are often preferred. Compounds wherein X represents C—H, however, are sometimes preferred. The compounds of the invention include compounds of Formula I wherein Q represents N or C—H. Each of these two options is sometimes preferred. Under many circumstances, compounds wherein X represents N and Q represents C—H are preferred but, under other circumstance

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