Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-03-30
2001-08-21
Raymond, Richard L. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C546S141000, C546S120000, C514S309000, C514S274000, C514S414000, C514S254080, C514S303000, C514S406000, C514S266400, C514S403000, C514S392000, C514S384000, C514S242000, C544S310000, C544S236000, C544S223000, C544S235000, C544S282000, C544S182000, C548S455000, C548S364700, C548S360100, C548S312100, C548S263200
Reexamination Certificate
active
06277847
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to herbicidal compounds of formula (I), methods of making such herbicidal compounds and methods of using such herbicidal compounds. This invention also relates to intermediates used in the preparation of such herbicidal compounds.
BACKGROUND OF THE INVENTION
There is a continuing demand for new herbicides. Herbicides are useful for controlling unwanted vegetation, i.e., weeds, which may otherwise cause significant damage to crops such as wheat, corn, soybeans and cotton, to name a few. For crop protection, so-called “selective” herbicides are desired that control the weeds without damaging the crop to any significant degree. Such crops are said to exhibit tolerance to the herbicide. In certain other situations, it is desirable to use herbicides that provide complete vegetation control such as in areas around railroad tracks and other structures. While many commercial products are available that provide selective or complete vegetation control, demand exists for new herbicides that are more effective and less costly, and meet requisite safety characteristics. Additionally, as an aid to harvesting there is also a demand for new, safe, more effective, and less costly compounds that cause defoliation and/or desiccation of cultivated plant parts. Such compounds would be useful in the harvesting of, for example, cotton, potatoes, rape, sunflowers, soybeans and broadbeans.
OBJECTS AND SUMMARY OF THE INVENTION
It has now been found that certain novel isoindolinonyl- and 3,4-dihydroisoquinolonyl-substituted heterocycles are useful as pre-emergent and post-emergent herbicides. These herbicidally effective compounds are represented by formula (I):
X, Y and Z are as follows: (i) X is hydrogen, halogen, alkyl, haloalkyl, alkoxyl, haloalkoxyl, cyano, amido or nitro; Y is hydrogen, halogen, alkyl, or haloalkyl; and Z is hydrogen, alkyl, halogen, amino, nitro, alkoxyl, hydroxyl or haloalkoxyl with the proviso that when Z is alkyl, halogen, amino, nitro, alkoxyl, hydroxyl or haloalkoxyl, X is not a hydrogen and Y is not a hydrogen; or (ii) X and Z are connected to each other to form part of a 4, 5 or 6 membered ring and Y is as defined above, or Y and Z are connected to each other to form part of a 4, 5 or 6 membered ring and X is as defined above;
n is 1 or 2;
R is hydrogen, amino, alkyl, haloalkyl, cyanoalkyl, hydroxyl, alkoxyl, alkoxyalkyl, cycloalkylalkyl, alkenyl, alkenoxy, alkynyl, alkoxycarbonylalkyl, or phenylalkyl; and
R
1
is hydrogen, amino, alkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, arylalkyl, alkenyl, alkynyl, alkoxycarbonylalkyl, or salts thereof.
The present invention is also directed to compounds of formulas (II) and (III), which are used as intermediates in the preparation of formula (I). Formula (II) is as follows:
wherein:
X, Y and Z are as follows: (i) X is hydrogen, halogen, alkyl, haloalkyl, alkoxyl, haloalkoxyl, cyano, amido or nitro; Y is hydrogen, halogen, alkyl, or haloalkyl; and Z is hydrogen, alkyl, halogen, amino, nitro, alkoxyl, hydroxyl or haloalkoxyl with the proviso that when Z is alkyl, halogen, amino, nitro, alkoxyl, hydroxyl or haloalkoxyl, X is not a hydrogen and Y is not a hydrogen; or (ii) X and Z are connected to each other to form part of a 4, 5 or 6 membered ring and Y is as defined above, or Y and Z are connected to each other to form part of a 4, 5 or 6 membered ring and X is as defined above;
n is 1 or 2, and;
R is hydrogen, amino, alkyl, haloalkyl, cyanoalkyl, hydroxyl, alkoxyl, alkoxyalkyl, cycloalkylalkyl, alkenyl, alkenoxyl, alkynyl, alkoxycarbonylalkyl, or phenylalkyl.
Formula (III) is as follows:
wherein Q is:
X, Y and Z are as follows: (i) X is hydrogen, halogen, alkyl, haloalkyl, alkoxyl, haloalkoxyl, cyano, amido or nitro; Y is hydrogen, halogen, alkyl, or haloalkyl; and Z is hydrogen, alkyl, halogen, amino, nitro, alkoxyl, hydroxyl or haloalkoxyl with the proviso that when Z is alkyl, halogen, amino, nitro, alkoxyl, hydroxyl or haloalkoxyl, X is not a hydrogen and Y is not a hydrogen; or (ii) X and Z are connected to each other to form part of a 4, 5 or 6 membered ring and Y is as defined above, or Y and Z are connected to each other to form part of a 4, 5 or 6 membered ring and X is as defined above;
R
1
is hydrogen, amino, alkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, arylalkyl, alkenyl, alkynyl, alkoxycarbonylalkyl, or salts thereof;
R
2
is methyl or halomethyl, and;
R
3
is alkyl.
The present invention is further directed to methods of using and making compounds of formula (I), herbicidal compositions comprising at least one compound of formula (I) and pesticidal compositions comprising at least one compound of formula (I).
DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to certain new and useful agricultural compounds, namely, certain novel isoindolinonyl- and 3,4-dihydroisoquinolonyl-substituted heterocycles, that possess pre-emergent and post-emergent herbicidal activity. These compounds are represented by formula (I) as defined hereinabove.
The alkyl group which may represent X in formula (I) may be a substituted or unsubstituted, branched or straight chain, alkyl group containing C
1
-C
10
carbon atoms, preferably, C
1
-C
6
carbon atoms. The alkyl portion of the haloalkyl group, alkoxyl group and haloalkoxyl group which may represent X in formula (I) may be a substituted or unsubstituted, branched or straight chain, alkyl group containing C
1
-C
6
carbon atoms, preferably, C
1
-C
3
carbon atoms. The halogen atom which may represent X in formula (I) may be a chlorine atom, fluorine atom, bromine atom or iodine atom, preferably, a chlorine atom.
The alkyl group, as well as the alkyl portion of the haloalkyl group, which may represent Y in formula (I) may be a substituted or unsubstituted, branched or straight chain, alkyl group containing C
1
-C
6
carbon atoms, preferably, C
1
-C
3
carbon atoms. The halogen which may represent Y in formula (I) may be a chlorine atom, bromine atom or fluorine atom, preferably, a chlorine atom.
The alkyl group, as well as the alkyl portion of the haloalkyl group, which may represent R in formula (I) may be a substituted or unsubstituted, branched or straight chain, alkyl group containing C
1
-C
10
carbon atoms, preferably C
1
-C
6
. The alkyl portion of the alkoxyl group which may represent R in formula (I) may be a substituted or unsubstituted, branched or straight chain, alkyl group containing C
1
-C
6
carbon atoms, preferably, C
1
-C
3
carbon atoms. The phenylalkyl group representing R in formula (I) may be substituted with, for example, one or more of a halogen atom or alkoxyl group.
The alkyl group which may represent R
1
in formula (I) may be a substituted or unsubstituted, branched or straight chain, alkyl group containing C
1
-C
6
carbon atoms, preferably, C
1
-C
3
carbon atoms.
The structural moieties representing Q in formula (I) may also be identified by their chemical names as follows:
where “Q1” is 1-substituted-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl; “Q2” is 3,4,5,6-tetrahydrophthalimid-1-yl; “Q3” is 1,6,8-triazabicyclo[4.3.0]nonane-7,9-dion-8-yl; “Q4” is 5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-A]pyridin-3(2H)-on-2-yl; “Q5” is 1-methyl-6-trifluoromethyl-1,3,5-triazine-2,4-dione-3-yl; “Q6” is 4-chloro-5-difluoromethoxy-1-methylpyrazol-3-yl; “Q7” is 5,6,7,8-tetrahydro-1H,3H[1,3,4]thiadiazolo[3,4-a]pyridazineimin-1-yl; “Q8” is 1,2,3,6-tetrahydro-6-azaindolizin-5,7-dion-6-yl; “Q9” is 3-chloro-4,5,6,7-tetrahydroindazol-3-yl; “Q10” is 1-(1-methylethyl)imidazolidine-2,4-dion-3-yl; “Q11” is 4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl; and “Q12” is 4-methyl-1,2,4-triazine-3,5-dion-2-yl.
Where X and Z or Y and Z are connected to form part of a 4, 5 or 6 membered ring, X and Z or Y and Z, taken together, may be: —C
3
H
6
—, —C
4
H
8
—, —CH
2
CH
2
O—, —CH
2
CH
2
C(CH
3
)
2
O—, —OCH
2
O—, —OCH
2
CH
2
O—, —OCF
2
CF
2
—, —CF
2
CF
2
O—, —OCF
2
O—, —OCF
2
CF
2
O—, CH═CHCH═CH—, —CH═CHO—, —CH═CHN—, —CH═C(Br)N—, —CH═C(CF
3
)N—,
Crawford Scott D.
Theodoridis George
FMC Corporation
FMC Corporation
Liu Hong
Raymond Richard L.
LandOfFree
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