Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-08-08
2003-08-26
Rotman, Alan L. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C504S244000
Reexamination Certificate
active
06610853
ABSTRACT:
TECHNICAL FIELD
The present invention relates to N-(phenylsulfonyl)-picolinamide derivatives, a process for producing the same and a herbicide comprising said derivatives as an active ingredient.
TECHNICAL BACKGROUND
The following N-(phenylsulfonyl)picolinamide derivatives have been known heretofore.
N-[(4-Methylphenyl)sulfonyl]picolinamide (U.S. Pat. No. 5,294,610).
N-[(4-Aminophenyl)sulfonyl]picolinamide.
There is however no report that N-(phenylsulfonyl)-picolinamide derivatives can be used as an effective ingredient of herbicides.
By the way, there have conventionally been strong demands for herbicides capable of exhibiting excellent herbicidal activity even at such low application dosages as bringing about advantage of reducing the amount present in the environment, herbicides capable of exhibiting selectivity between crops and weeds irrespective of variations in environmental conditions, herbicides free from crop injury to the second crop in double-cropping, etc.
The present invention has been completed with a view toward meeting such demands as described above.
DISCLOSURE OF THE INVENTION
Accordingly, objects of the present invention are to provide novel compounds exhibiting excellent herbicidal effect, processes for producing the same, and novel herbicides comprising the same compound as the active ingredient.
As the result of various studies in order to find N-(phenylsulfonyl)picolinamide derivatives industrially effective, the present inventors have found that N-(phenylsulfonyl)-picolinamide derivatives have high herbicidal effect, and thus the present invention has been completed.
The present invention has the following constituent features.
The first invention relates to a herbicide comprising an N-(phenylsulfonyl)picolinamide derivative of the following formula (I) as the active ingredient:
wherein X represents halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, (C1-C4 alkoxy)carbonyl group, (di-C1-C4 alkylamino)sulfonyl group, [N—(C1-C4 alkyl)-N—(C1-C4 alkoxy)amino]sulfonyl group, (C1-C4 alkylamino)sulfonyl group, C1-C4 alkylthio group, C1-C4 alkylsulfinyl group, C1-C4 alkylsulfonyl group or nitro group,
n is an integer of 0-5. In case of n being 2 or more, each X may be identical or different,
Y represents halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C4 alkylthio group, C1-C4 haloalkylthio group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, (C1-C4 alkoxy) C1-C4 alkyl group, (C1-C4 alkylthio) C1-C4 alkyl group or nitro group,
m is an integer of 0-4, and each Y may be identical or different in case of m being 2 or more.
The second invention relates to a process for producing an N-(phenylsulfonyl)picolinamide derivative of the following formula (I) which comprises condensing a substituted picolinic acid of the formula (II) with a substituted benzenesulfonamide of the formula (III) under dehydration, which is shown in the following reaction formula (The first process for production):
wherein X, Y, n and m are each the same definition as described above.
The third invention relates to a process for producing an N-(phenylsulfonyl)picolinamide derivative of the formula (I) which comprises reacting a substituted picolinic phenyl ester of the formula (IV) with a substituted benzenesulfonamide of the formula (III) in the presence of a basic compound, which is shown in the following reaction formula (the second process for production).
wherein X, Y, n and m are each the same definition as described above,
Z represents halogen atom, C1-C4 alkyl group, C1-C4 alkoxy group or nitro group, s is an integer of 0-5, and each Z may be identical or different in case of s being 2 or more.
The fourth invention relates to an N-(phenylsulfonyl)-picolinamide derivative of the following formula (I):
wherein X, Y, n and m are each the same definition as described above, exclusive of N-[(4-methylphenyl)sulfonyl]picolinamide.
BEST MODE OF PRACTICING THE INVENTION
The present invention will be illustrated in detail in the following.
The groups X and Y of the N-(phenylsulfonyl)picolinamide derivatives of the above-described formula (I) according to the present invention include the following typical substituents, and n and m are preferred to be the following values.
Regarding X:
Fluorine atom, chlorine atom and bromine atom as the halogen atom.
Methyl group as the C1-C4 alkyl group.
Trifluoromethyl group as the C1-C4 haloalkyl group.
Methoxy group as the C1-C4 alkoxy group.
Trifluoromethoxy group as the C1-C4 haloalkoxy group.
Methoxycarbonyl group as the (C1-C4 alkoxy)carbonyl group.
(Dimethylamino)sulfonyl group, (diethylamino)sulfonyl group and (methylethylamino)sulfonyl group as the (di-C1-C4 alkylamino)sulfonyl group. In this case, each C1-C4 alkyl may be identical or different.
(N-Methyl-N-methoxyamino)sulfonyl group as the [N—(C1-C4 alkyl)-N—(C1-C4 alkoxy)amino]sulfonyl group.
Methylaminosulfonyl group as the (C1-C4 alkylamino)-sulfonyl group.
Methylthio group as the C1-C4 alkylthio group.
Methylsulfinyl group as the C1-C4 alkylsulfinyl group.
Methylsulfonyl group as the C1-C4 alkylsulfonyl group.
Preferred examples of these groups include fluorine atom, chlorine atom, methyl group, trifluoromethyl group, methoxy group, trifluoromethoxy group, methoxycarbonyl group, (dimethylamino)-sulfonyl group, (N-methyl-N-methoxyamino)sulfonyl group, methylthio group, methylsulfinyl group and methylsulfonyl group.
A preferred range of n is 0 to 3, more preferably 0 to 2.
Since the preferred positions of X attached to the benzene ring are ortho positions to the N-substituted sulfamoyl group, it is preferred that the X attaches to one or both of them.
Regarding Ym:
Fluorine atom, chlorine atom and bromine atom as the halogen atom.
Methyl group, ethyl group and 1-methylethyl group as the C1-C4 alkyl group.
Fluoromethyl group, difluroromethyl group and trifluoromethyl group as the C1-C4 haloalkyl group.
Methoxy group, ethoxy group and (1-methylethyl)oxy group as the C1-C4 alkoxy group.
Difluoromethoxy group, trifluoromethoxy group, (2-fluoroethyl)oxy group, (2,2-difluoroethyl)oxy group, (2,2,2-trifluoroethyl)oxy group, (1,1,2,2-tetrafuruoroethyl)oxy group, (2-chloro-1,1,2-trifluoroethyl)oxy group and (3,3,3-trifluroropropyl)oxy group as the C1-C4 haloalkoxy group.
Methylthio group as the C1-C4 alkylthio group.
Difluoromethylthio group as the C1-C4 haloalkylthio group.
Methylamino group as the C1-C4 alkylamino group.
Dimethylamino group and methyl ethyl amino group. In this case, each C1-C4 alkyl may be identical or different.
Methoxymethyl group as (C1-C4 alkoxy) C1-C4 alkyl group.
Methylthiomethyl group as the (C1-C4 alkylthio) C1-C4 alkyl group.
Preferred examples of these groups include fluorine atom, chlorine atom, bromine atom, methyl group, 1-methylethyl group, fluoromethyl group, trifluoromethyl group, methoxy group, ethoxy group, (1-methylethyl)oxy group, difluoromethoxy group, trifluoromethoxy group, methylthio group, difluoromethylthio group, methylamino group, dimethylamino group, etc.
A preferred range of m is 0 to 3, more preferably 0 to 2.
Since the preferred positions of Y attached to the pyridine ring are 4-, 5-and 6-positions when the nitrogen atom of the pyridine ring is 1-position and the N-substituted carbamoyl group is 2-position, Y is preferred to be attached to at least one of them.
Specific examples of the N-(phenylsulfonyl)picolinamide derivatives of the above described formula (I) according to the present invention include those as shown in Table 1.
The columns of substituent Xn and Ym in the Table 1 have the following common rule.
Xn: “position-substituent” is described as the case that the N-substituted sulfamoyl group on the benzene ring is I-position.
Accordingly, “2-CF
3
” means that the CF
3
is attached to 2-position.
Similarly, “2-COOCH
3
” means that the COOCH
3
is attached to 2-position, and “2-Cl” means that a chlorine atom is attached to 2-position. These cases correspond to n being 1.
“2
Kanda Yoichi
Sato Koki
Sato Tsutomu
Coppins Janet L
Kureha Kagaku Kogyo K.K.
McDermott & Will & Emery
Rotman Alan L.
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