Pyridine derivatives and their herbicidal compositions
First Claim
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1. A pyridine derivative having the formula:
- ##STR234## wherein one of A, B, D and E is an oxygen atom, a sulfur atom, --SO--, --SO2 -- or --NR3 --, with the rest being all carbon atoms, one double bond may or may not be present in the ring;
X is a halogen atom, a C1 -C4 alkyl group, a C1 -C4 alkoxy group, a C1 -C4 haloalkyl group, a C1 -C4 haloalkoxy group, a C1 -C4 alkylthio group, a C1 -C4 haloalkylthio group, a C1 -C4 alkoxycarbonyl group, a C1 -C4 alkylthioalkyl group, a tetrahydrothiopyranyl group, a hydroxyl group, a CF3 group or a phenyl or pyridyl group (which may be substituted by C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 alkylthio, CF3, nitro or halogen);
n is an integer of from 0 to 6, and when n is an integer of from 2 to 6, the plurality of X may be the same or different;
W is an oxygen atom or a sulfur atom;
R is a hydrogen atom, a di-lower alkylimino group, a C1 -C5 alkyl group (which may be substituted by C1 -C3 alkoxy, hydroxyl, C3 -C6 halocycloalkyl carboxyl, lower alkoxycarbonyl, cyano, dialkylphosphonyl, halogen, benzyloxy, tri-lower alkylammonium or phenyl which may be substituted by halogen, C1 -C4 alkyl, C1 -C4 alkoxy or nitro), a C2 -C5 alkenyl group (which may be substituted by C1 -C3 alkoxy, lower alkoxycarbonyl, two C1 -C3 alkoxy or phenyl), a C2 -C5 alkynyl group, a C4 or C5 oxacycloalkyl group, a C2 -C5 mono-, di- or tri-haloalkenyl group, a C2 -C5 haloalkynyl group, a glycidyl group, a furfuryl group, an alkylthioalkyl group, a C3 -C6 cycloalkyl group which may be substituted by C1 -C3 alkyl, or a cation selected from the group consisting of an alkali metal ion, an alkaline earth metal ion, an ammonium ion or a quaternary ammonium ion;
R1 is a C1 -C4 alkyl group, R2 is a C1 -C4 alkyl group or a C3 -C6 cycloalkyl group, or R1 and R2 together with the adjacent carbon atom, form a C3 -C6 cycloalkyl group which may be substituted by C1 -C3 alkyl; and
R3 is a hydrogen atom or a C1 -C3 alkyl group;
or an optical isomer of the derivative when R1 and R2 are different from each other.
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Abstract
A pyridine derivative having the formula: ##STR1## wherein one of A, B, D and E is oxygen, sulfur, --SO--, --SO2 --, --NR3 --, ##STR2## or ═CH-- with the rest being all carbon atoms; X is halogen, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 haloalkyl, C1 -C4 haloalkoxy, C1 -C4 alkylthio, C1 -C4 haloalkylthio, C1 -C4 alkoxycarbonyl, C1 -C4 alkylthioalkyl, tetrahydrothiopyranyl, hydroxyl, CF3, phenyl or pyridyl; n is an integer of from 0 to 6,; W is oxygen or sulfur; R is hydrogen, di-lower alkylimino, C1 -C5 alkyl, C2 -C5 alkenyl, C2 -C5 alkynyl, C4 or C5 oxacycloalkyl, C2 -C5 mono-, di- or tri-haloalkenyl, C2 -C5 haloalkynyl, glycidyl, furfuryl, alkylthioalkyl, C3 -C6 cycloalkyl or a cation R1 is C1 -C4 alkyl, R2 is C1 -C4 alkyl or C3 -C6 cycloalkyl, or R1 and R2 together with the ajacent carbon atom, form C3 -C6 cycloalkyl; and R3 is hydrogen or C1 -C3 alkyl. The compounds are used as herbicides.
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Citations
9 Claims
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1. A pyridine derivative having the formula:
- ##STR234## wherein one of A, B, D and E is an oxygen atom, a sulfur atom, --SO--, --SO2 -- or --NR3 --, with the rest being all carbon atoms, one double bond may or may not be present in the ring;
X is a halogen atom, a C1 -C4 alkyl group, a C1 -C4 alkoxy group, a C1 -C4 haloalkyl group, a C1 -C4 haloalkoxy group, a C1 -C4 alkylthio group, a C1 -C4 haloalkylthio group, a C1 -C4 alkoxycarbonyl group, a C1 -C4 alkylthioalkyl group, a tetrahydrothiopyranyl group, a hydroxyl group, a CF3 group or a phenyl or pyridyl group (which may be substituted by C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 alkylthio, CF3, nitro or halogen);
n is an integer of from 0 to 6, and when n is an integer of from 2 to 6, the plurality of X may be the same or different;
W is an oxygen atom or a sulfur atom;
R is a hydrogen atom, a di-lower alkylimino group, a C1 -C5 alkyl group (which may be substituted by C1 -C3 alkoxy, hydroxyl, C3 -C6 halocycloalkyl carboxyl, lower alkoxycarbonyl, cyano, dialkylphosphonyl, halogen, benzyloxy, tri-lower alkylammonium or phenyl which may be substituted by halogen, C1 -C4 alkyl, C1 -C4 alkoxy or nitro), a C2 -C5 alkenyl group (which may be substituted by C1 -C3 alkoxy, lower alkoxycarbonyl, two C1 -C3 alkoxy or phenyl), a C2 -C5 alkynyl group, a C4 or C5 oxacycloalkyl group, a C2 -C5 mono-, di- or tri-haloalkenyl group, a C2 -C5 haloalkynyl group, a glycidyl group, a furfuryl group, an alkylthioalkyl group, a C3 -C6 cycloalkyl group which may be substituted by C1 -C3 alkyl, or a cation selected from the group consisting of an alkali metal ion, an alkaline earth metal ion, an ammonium ion or a quaternary ammonium ion;
R1 is a C1 -C4 alkyl group, R2 is a C1 -C4 alkyl group or a C3 -C6 cycloalkyl group, or R1 and R2 together with the adjacent carbon atom, form a C3 -C6 cycloalkyl group which may be substituted by C1 -C3 alkyl; and
R3 is a hydrogen atom or a C1 -C3 alkyl group;
or an optical isomer of the derivative when R1 and R2 are different from each other. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9)
- ##STR234## wherein one of A, B, D and E is an oxygen atom, a sulfur atom, --SO--, --SO2 -- or --NR3 --, with the rest being all carbon atoms, one double bond may or may not be present in the ring;
Specification
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Current AssigneeNissan Chemical Industries Limited (Nissan Chemical Corporation)
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Original AssigneeNissan Chemical Industries Limited (Nissan Chemical Corporation)
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InventorsWatanabe, Junichi, Hattori, Kenji, Nawamaki, Tsutomu, Ikai, Takasi, Hatanaka, Masataka, Numata, Tatsuo
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Primary Examiner(s)Jiles, Henry R.
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Assistant Examiner(s)Dentz, Bernard I.
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Application NumberUS06/882,408Time in Patent Office449 DaysField of Search546/15, 546/114, 546/115, 546/116, 546/122, 546/123, 71/90, 71/91, 71/94US Class Current504/246CPC Class CodesA01N 43/50 1,3-Diazoles; Hydrogenated ...A01N 43/90 having two or more relevant...C07D 401/04 directly linked by a ring-m...C07D 471/04 Ortho-condensed systemsC07D 491/04 Ortho-condensed systemsC07D 495/04 Ortho-condensed systems
