Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
1998-06-15
2002-01-08
O'Sullivan, Peter (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C560S045000, C504S260000, C504S289000, C504S315000, C546S316000, C546S326000, C546S329000, C546S335000, C549S072000, C549S077000, C549S080000
Reexamination Certificate
active
06337417
ABSTRACT:
TECHNOLOGICAL FIELD
This invention relates to herbicides, and more particularly to N-phenyltetrahydrophthalamic acid derivatives which are novel compounds, to methods of producing the same, and to herbicides containing the same as the effective components, and to imidoylchloride derivatives as the intermediate products, and to methods of producing the same. N-phenyltetrahydrophthalamic acid derivatives of the present invention exhibit excellent herbicidal activity. The derivatives are useful as herbicides which can be widely applied to upland, paddy field, orchard, pasture, turf, forest, non-crop land, etc. The derivatives are not harmful to crops.
BACKGROUND TECHNOLOGY
Hitherto, herbicidal activity of tetrahydrophthalamic acid derivatives is well known. For example, N-(4′-chlorophenyl)-3, 4, 5, 6-tetrahydrophthalamic acid methyl ester is known, as is disclosed in JP-A-48-44425.
However, the conventional tetrahydrophthalamic acid derivatives are not necessarily sufficient in herbicidal activity or are substantially limited in herbicidal spectrum against weeds. Furthermore, these derivatives are insufficient in selectivity between crops and weeds, thereby inducing problems of safety for crops.
It is an object of the present invention to solve the aforementioned problems, and to provide novel compounds which are excellent in herbicidal activity but not harmful to crops, methods of producing the same and herbicides containing the same as the effective components, and the intermediate products and method of producing the same.
DISCLOSURE OF THE INVNTION
The inventors have found and already proposed that novel tetrahydrophthalamic acid derivatives each having a specific substituent acyl group bonded to an amide nitrogen atom are very excellent in herbicidal activity, selectivity and herbicidal spectrum (International Application PCT/JP91/01109). In view of this, the inventors have intensely studied and as a result have completed the present invention as follows.
That is, the present invention provides N-phenyltetrahydrophthalamic acid derivatives represented by the general formula [I], methods of producing the same, and herbicides containing the same as the effective components:
wherein X and Y each individually represent hydrogen atoms or halogen atoms, R
1
represents a lower alkoxycarbonylalkylthio group, R
2
represents a lower alkyl group, a halogenated lower alkyl group or a substituted or unsubstituted phenyl group, and R
3
represents a lower alkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, or a lower alkoxyalkoxy group.
Furthermore, the present invention provides N-phenyltetrahydrophthalamic acid derivatives represented by the general formula [II], methods of producing the same, and herbicides containing the same as the effective components:
wherein X′ and Y′ each individually represent hydrogen atoms or halogen atoms, R
4
represents a hydrogen atom, a lower alkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, cycloalkyloxy group, a lower alkoxycarbonyl group, a lower alkoxycarbonylalkoxy group or a lower alkoxycarbonylalkylthio group, R
5
represents:
wherein R
7
represents a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxycarbonyl group, and R
8
represents a hydrogen atom, a halogen atom or a lower alkyl group, and R
6
represents a lower alkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, a cycloalkyloxy group or a lower alkoxyalkoxy group.
Still furthermore, the present invention provides imidoylchloride derivatives represented by the general formula [III] and method of producing the same:
wherein X and Y each individually represent hydrogen atoms or halogen atoms, R
1
represents a lower alkoxycarbonylalkylthio group, and R
2
represents a lower alkyl group, a halogenated lower alkyl group or a substituted or unsubstituted phenyl group.
Furthermore, the present invention provides imidoylchloride derivatives represented by the general formula [IV] and method of producing the same:
wherein X′ and Y′ each individually represent hydrogen atoms or halogen atoms, R
4
represents a hydrogen atom, a lower alkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, cycloalkyloxy group, a lower alkoxycarbonyl group, a lower alkoxycarbonylalkoxy group or a lower alkoxycarbonylalkylthio group, R
5
represents:
wherein R
7
represents a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxycarbonyl group, and R
8
represents a hydrogen atom, a halogen atom or a lower alkyl group.
As concrete examples of N-phenyltetrahydrophthalamic acid derivatives [I] which are compounds of the present invention are, there can be cited, for example, N-acetyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrahydrophthalamic acid methyl ester, N-acetyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrahydrophthalamic acid ethyl ester, N-acetyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrahydrophthalamic acid-n-propyl ester, N-acetyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrahydrophthalamic acid-iso-propyl ester, N-acetyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrehydrophthalamic acid-n-butyl ester, N-acetyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrahydrophthalamic acid-n-pentyl ester, N-acetyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrahydrophthalamic acid allyl ester, N-acetyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrehydrophthalamic acid propargyl ester, N-acetyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrehydrophthalamic acid methoxymethyl ester, N-acetyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrahydrophthalamic acid ethoxymethyl ester, N-acetyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrehydrophthalamic acid-2-methoxyethyl ester, N-acetyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrahydrophthalamic acid-2-ethoxyethyl ester, N-propionyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrahydrophthalamic acid methyl ester, N-propionyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrahydrophthalamic acid ethyl ester, N-propionyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrahydrophthalamic acid-n-propyl ester, N-propionyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrehydrophthalamic acid-iso-propyl ester, N-propionyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrehydrophthalamic acid-n-butyl ester, N-propionyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrehydrophthalamic acid-n-pentyl ester, N-propionyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrehydrophthalamic acid allyl ester, N-propionyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrehydrophthalamic acid propargyl ester, N-propionyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrehydrophthalamic acid methoxymethyl ester, N-propionyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrahydrophthalamic acid ethoxymethyl ester, N-propionyl-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrahydrophthalamic acid-2-methoxyethyl ester, N-propionyl-N-(4-chloro-2-fluoro-5-methoxy-carbonylmethylthiophenyl)-3,4,5,6-tetrahydrophthalamic acid-2-ethoxyethyl ester, N-(2-chloroacetyl)-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrahydrophthalamic acid methyl ester, N-(2-chloroacetyl)-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrahydrophthalamic acid ethyl ester, N-(2-chloroacetyl)-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrehydrophthalamic acid-n-propyl ester, N-(2-chloroacetyl)-N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-3,4,5,6-tetrahydrophthalamic acid-iso-propyl ester, N-(2-chloroacetyl)-
Ikeda Yukio
Kawamura Matsue
Kohda Yumiko
Komata Takeo
Kume Takashi
Central Glass Co. Ltd.
Crowell & Moring LLP
O'Sullivan Peter
LandOfFree
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