Triazole sulfones having herbicidal activity

Details Triazole sulfones having herbicidal activity Triazole sulfones having herbicidal activity

2000-01-13

2002-10-08

Morris, Patricia L. (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S264400

Reexamination Certificate

active

06461997

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to herbicidal compounds useful in agriculture and related industries. More specifically, the present invention relates to a new class of compounds effective as selective herbicides, to compositions comprising such compounds, and to methods of controlling weeds with such compounds and compositions thereof.
BACKGROUND OF THE INVENTION
Triazole derivatives have, for many years, been investigated for a wide range of utilities. For example, Potts, Chemical Reviews, 61, 87-127 (1961) is cited in U.S. Pat. No. 3,308,131 as showing that various 1,2,4-triazole compounds have found commercial application as herbicides, defoliants, photographic reagents, rubber chemicals and in polymers. U.S. Pat. No. 3,308,131 itself discloses 1,2,4-triazole compounds having a di-aliphatically substituted tertiary carbamoyl group attached to a nitrogen atom of the triazole nucleus, and in which the carbon atoms of the triazole nucleus are bonded to hydrogen, halogen, carbon or sulfur atoms. These triazoles are disclosed to be particularly useful as insecticides.
Other 1,2,4-triazoles have been disclosed as having utility as herbicides. For example, U.S. Pat. No. 5,211,739 discloses herbicidal 1-(disubstituted carbamoyl or thiocarbamoyl)-1,2,4-triazol-3-yl sulfonates and thiosulfonates. U.S. Pat. No. 3,952,001 discloses herbicidal 1-carbamoyl-1,2,4-triazoles having haloalkylsulfinyl or haloalkylsulfonyl substituents but teaches that the “haloalkyl radical” is preferably “attached to a carbon atom other than that which is attached to the . . . sulphur atom of the group” defined as the haloalkylsulfinyl or haloalkylsulfonyl moiety. U.S. Pat. No. 4,810,271 discloses herbicidal 1-(disubstituted carbamoyl or thiocarbamoyl)-1,2,4-triazol-3-yl cycloalkyl(lower)alkyl, oxacycloalkyl(lower)alkyl or dioxacycloalkyl(lower)alkyl sulfonates and thiosulfonates. U.S. Pat. No. 4,280,831 discloses one herbicidal compound which is 3-benzylsulfonyl-1-diethylcarbamoyl-1,2,4-triazole.
SUMMARY OF THE INVENTION
The present invention provides a compound of formula (I)
wherein R
3
is hydrogen, halogen or a group having a molecular weight of 15 to about 500, having up to 34 carbon atoms and comprising a hydrocarbyl moiety that is unsubstituted or substituted with one or more heteroatom-containing groups wherein heteroatoms are selected from oxygen, sulfur, nitrogen, halogen and silicon, and Z is a carbamoyl or thiocarbamoyl group having directly attached to the nitrogen atom thereof, each by a carbon-nitrogen bond, two substituent groups each independently comprising a C
1-14
hydrocarbyl moiety that is unsubstituted or substituted with one or more heteroatom-containing groups wherein heteroatoms are selected from oxygen, nitrogen and halogen, said substituent groups optionally being joined to form, with said nitrogen atom, a ring structure, Z having a molecular weight of 72 to about 500; or an agronomically acceptable acid addition salt or metal complex of a compound of formula (I).
More particularly, the present invention provides a compound of formula (II)
wherein:
Y is oxygen or sulfur;
R
1
and R
2
(a) are each independently a C
1-14
hydrocarbyl group, preferably a linear or branched aliphatic or alicyclic group that is saturated or has one or more olefinic and/or acetylenic bonds, and is unsubstituted or substituted with one or more halogen, haloalkyl, hydroxy, alkoxy, carboxy, amido, cyano or amino groups, wherein amido and amino groups are each unsubstituted or further substituted with one or two hydrocarbyl groups; or
(b) together with the carbamoyl nitrogen atom to which they are attached, form a nitrogen-containing five or six membered ring, the ring being optionally interrupted by an ethereal oxygen atom and unsubstituted or substituted with one or more hydroxy, amido, cyano, amino or C
1-8
alkyl, alkenyl, alkynyl, cycloalkyl, arylalkyl, alkoxy, aminoalkyl or haloalkyl groups, wherein amido and amino groups are each unsubstituted or further substituted with one or two hydrocarbyl groups;
R
1
and R
2
, together with the carbamoyl or thiocarbamoyl group to which they are attached, having a total molecular weight of 72 to about 500; and
R
3
is hydrogen, halogen, or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, cycloalkylalkenyl, aryl, arylalkyl, alkylthio or arylalkylthio group that is unsubstituted or substituted with one or more halo, hydroxy, alkoxy, acetyloxy, benzoyloxy, alkoxycarbonyl, silyl or alkylsilyl groups, wherein aryl rings are unsubstituted or substituted with one to three substituents independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, halo, haloalkyl, alkoxy, haloalkoxy, cyano, nitro, alkoxycarbonyl, alkylthio and haloalkylthio groups; R
3
having a molecular weight of 15 to about 500 and having 0-34 carbon atoms;
or an agronomically acceptable acid addition salt or metal complex of a compound of formula (II).
Illustratively, R
1
and R
2
can be alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkylcycloalkyl, alkenylcycloalkyl, alkynylcycloalkyl, cycloalkylalkyl, cycloalkenylalkyl, alkylcycloalkylalkyl, alkenylcycloalkylalkyl, alkynylcycloalkylalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkoxyalkyl, alkoxyalkenyl, alkoxyalkynyl, alkoxycycloalkyl, haloalkoxyalkyl, haloalkoxyalkenyl, haloalkoxyalkynyl, haloalkoxycycloalkyl, halocycloalkylalkyl or alkoxycycloalkylalkyl groups. Alternatively, R
1
and R
2
can illustratively together form a C
4-5
alkylene group that is unsubstituted or substituted with one or two substituents independently selected from halo, hydroxy and alkoxy, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl and cycloalkenylalkyl groups unsubstituted or further substituted with halo, hydroxy, alkoxy, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl or haloalkoxy groups.
Illustratively, R
3
can be hydrogen, halogen or an alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkenyl, cycloalkylalkenyl, alkoxyalkenyl, haloalkenyl, cycloalkenyl, halocycloalkenyl, alkylthio, hydroxyalkylthio, alkoxyalkylthio, haloalkylthio, acetyloxyalkylthio, benzoyloxyalkylthio, alkoxycarbonylalkylthio group or an aryl, arylalkyl or arylalkylthio group unsubstituted or substituted as indicated above.
The present invention also provides a composition for use as a herbicide comprising a herbicidally effective amount of a compound of formula (I) or (II) as defined above or an agronomically acceptable acid addition salt or metal complex thereof. Such a composition can be a concentrate, further comprising one or more agronomically acceptable inert formulation ingredients or excipient substances, or it can be ready-to-use, further comprising an agronomically acceptable carrier.
The present invention also provides a method of using a compound of formula (I) or (II) as a herbicidal agent, comprising applying a herbicidally effective amount of such a compound to soil or plants.
DETAILED DESCRIPTION OF THE INVENTION
Preferred Substituents of Compounds of Formula (II)
In compounds of the invention as defined in formula (II) above, the following are preferred substituents.
Preferably R
1
and R
2
are independently C
1-6
alkyl, C
2-4
alkenyl, C
2-4
alkynyl, C
3-6
cycloalkyl, C
5-6
cycloalkenyl, (C
1-3
)alkyl(C
3-6
)cycloalkyl, (C
2-3
)alkenyl(C
3-6
)cycloalkyl, (C
2-3
)alkynyl(C
3-6
)cycloalkyl, halo(C
1-6
)alkyl, halo(C
2-4
)alkenyl, halo(C
2-4
)alkynyl, halo(C
3-6
)cycloalkyl, (C
1-4
)alkoxy(C
1-6
)alkyl, (C
1-4
)alkoxy(C
2-4
)alkenyl, (C
1-4
)alkoxy(C
2-4
)alkynyl), (C
1-4
)alkoxy(C
3-6
)cycloalkyl halo(C
1-4
)alkoxy(C
1-6
)alkyl, halo(C
1-4
)alkoxy(C
2-4
)alkenyl, halo(C
1-4
)alkoxy(C
2-4
)alkynyl, halo(C
1-4
)alkoxy(C
3-6
)cycloalkyl, (C
3-6
)cycloalkyl(C
1-4
)alkyl, (C
5-6
)cycloalkenyl(C
1-4
)alkyl, (C
1-4
)alkyl(C
3-6
)cycloalkyl(C
1-4
)alkyl, (C
1-4
)alkyl(C
5-6
)cycloalkenyl(C
1-4
)alkyl, (C
2-4
)alkenyl(C
3-6
)cycloalkyl(C
1-4
)alkyl, (C
2-4
)alkynyl(C
5-6
)cycloalkyl(C
1-4
)alkyl, halo(C
3-6
)cycloalkyl(C
1-4
)alkyl or (C
1-4
)alkoxy(C
3-6
)cycloalkyl(C
1-4
)alkyl; or R
1
and R
2
together represent an unsubstituted

Affiliated with

Also associated with

Rating

Triazole sulfones having herbicidal activity does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Triazole sulfones having herbicidal activity, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Triazole sulfones having herbicidal activity will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2999380