Heterocyclic compounds
First Claim
1. A compound of the formula ##STR18## wherein R1 is hydrogen, C1 -C4 alkyl, C3 -C4 alkenyl, C3 -C4 alkynyl, C2 -C6 alkoxyalkyl or C1 -C4 haloalkyl,R2 is hydrogen, C1 -C6 alkyl, C2 -C6 alkoxyalkyl, C4 -C7 cycloalkenyl-C1 -C4 alkyl that is unsubstituted or ring-substituted by from 1 to 3 C1 -C3 alkyl groups, C3 -C4 alkenyl, C4 -C7 cycloalkenyl-C3 -C5 alkenyl that is unsubstituted or ring-substituted by from 1 to 3 C1 -C3 alkyl groups, phenyl-C3 -C5 alkenyl wherein the phenyl group is unsubstituted or substituted by from 1 to 3 halogen atoms, C1 -C3 alkyl, C1 -C3 haloalkyl, C1 -C3 alkoxy, C1 -C3 alkylthio, C2 -C4 alkanoyl, C2 -C4 alkoxycarbonyl, C1 -C3 alkylsulfonyl, nitro or cyano, C3 -C4 alkynyl, C4 -C7 cycloalkenyl-C3 -C5 alkynyl that is unsubstituted or ring-substituted by from 1 to 3 C1 -C3 alkyl groups, or phenyl-C3 - C5 alkynyl wherein the phenyl group is unsubstituted or substituted by from 1 to 3 halogen atoms, C1 -C3 alkyl, C1 -C3 haloalkyl, C1 -C3 -alkoxy, C1 -C3 alkylthio, C2 -C4 alkanoyl, C2 -C4 alkoxycarbonyl, C1 -C3 alkylsulfonyl, nitro or cyano,R3 is hydrogen or halogen,R4 is hydrogen, halogen or C1 -C4 alkyl andR5 is C1 -C4 alkyl or C1 -C4 haloalkyl, orR4 and R5 together are tri- or tetra-methylene, with the proviso that, when R5 is C1 -C4 haloalkyl, R1 is other than C1 -C4 haloalkyl and R2 is other than hydrogen, and when R1 is C1 -C4 haloalkyl, R2 is other than hydrogen, C1 -C4 -alkyl, C3 -C4 alkenyl, C3 -C4 alkynyl and C2 -C6 alkoxyalkyl, or the corresponding enol ether of such a compound of formula I wherein R1 is other than hydrogen, C1 -C4 alkyl, C3 -C4 alkynyl and C1 -C4 haloalkyl, or a salt of such a compound of formula I wherein R1, R2 or both are hydrogen.
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Accused Products
Abstract
The invention relates to novel compounds of the formula ##STR1## wherein R1, R2, R3, R4 and R5 have the meanings given in the description, to enol ethers and salts thereof and their preparation, to weed control compositions that comprise such compounds as active ingredients, and to the use of the compounds or compositions to control weeds. The invention relates also to certain novel starting materials and to the preparation thereof.
33 Citations
9 Claims
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1. A compound of the formula ##STR18## wherein R1 is hydrogen, C1 -C4 alkyl, C3 -C4 alkenyl, C3 -C4 alkynyl, C2 -C6 alkoxyalkyl or C1 -C4 haloalkyl,
R2 is hydrogen, C1 -C6 alkyl, C2 -C6 alkoxyalkyl, C4 -C7 cycloalkenyl-C1 -C4 alkyl that is unsubstituted or ring-substituted by from 1 to 3 C1 -C3 alkyl groups, C3 -C4 alkenyl, C4 -C7 cycloalkenyl-C3 -C5 alkenyl that is unsubstituted or ring-substituted by from 1 to 3 C1 -C3 alkyl groups, phenyl-C3 -C5 alkenyl wherein the phenyl group is unsubstituted or substituted by from 1 to 3 halogen atoms, C1 -C3 alkyl, C1 -C3 haloalkyl, C1 -C3 alkoxy, C1 -C3 alkylthio, C2 -C4 alkanoyl, C2 -C4 alkoxycarbonyl, C1 -C3 alkylsulfonyl, nitro or cyano, C3 -C4 alkynyl, C4 -C7 cycloalkenyl-C3 -C5 alkynyl that is unsubstituted or ring-substituted by from 1 to 3 C1 -C3 alkyl groups, or phenyl-C3 - C5 alkynyl wherein the phenyl group is unsubstituted or substituted by from 1 to 3 halogen atoms, C1 -C3 alkyl, C1 -C3 haloalkyl, C1 -C3 -alkoxy, C1 -C3 alkylthio, C2 -C4 alkanoyl, C2 -C4 alkoxycarbonyl, C1 -C3 alkylsulfonyl, nitro or cyano, R3 is hydrogen or halogen, R4 is hydrogen, halogen or C1 -C4 alkyl and R5 is C1 -C4 alkyl or C1 -C4 haloalkyl, or R4 and R5 together are tri- or tetra-methylene, with the proviso that, when R5 is C1 -C4 haloalkyl, R1 is other than C1 -C4 haloalkyl and R2 is other than hydrogen, and when R1 is C1 -C4 haloalkyl, R2 is other than hydrogen, C1 -C4 -alkyl, C3 -C4 alkenyl, C3 -C4 alkynyl and C2 -C6 alkoxyalkyl, or the corresponding enol ether of such a compound of formula I wherein R1 is other than hydrogen, C1 -C4 alkyl, C3 -C4 alkynyl and C1 -C4 haloalkyl, or a salt of such a compound of formula I wherein R1, R2 or both are hydrogen.
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7. A weed control composition which comprises an effective amount of at least one compound of the formula ##STR19## wherein R1 is hydrogen, C1 -C4 alkyl, C3 -C4 alkenyl, C3 -C4 alkynyl, C2 -C6 alkoxyalkyl or C1 -C4 haloalkyl,
R2 is hydrogen, C1 -C6 alkyl, C2 -C6 alkoxyalkyl, C4 -C7 cycloalkenyl-C1 -C4 alkyl that is unsubstituted or ring-substituted by from 1 to 3 C1 -C3 alkyl groups, C3 -C4 alkenyl, C4 -C7 cycloalkenyl-C3 -C5 alkenyl that is unsubstituted or ring-substituted by from 1 to 3 C1 -C3 alkyl groups, phenyl-C3 -C5 alkenyl wherein the phenyl group is unsubstituted or substituted by from 1 to 3 halogen atoms, C1 -C3 alkyl, C1 -C3 haloalkyl, C1 -C3 alkoxy, C1 -C3 alkylthio, C2 -C4 alkanoyl, C2 -C4 alkoxycarbonyl, C1 -C3 alkyl-sulfonyl, nitro or cyano, C3 -C4 alkynyl, C4 -C7 cycloalkenyl-C3 -C5 alkynyl that is unsubstituted or ring-substituted by from 1 to 3 C1 -C3 alkyl groups, or phenyl-C3 - C5 alkynyl wherein the phenyl group is unsubstituted or substituted by from 1 to 3 halogen atoms, C1 -C3 alkyl, C1 -C3 haloalkyl, C1 -C3 -alkoxy, C1 -C3 alkylthio, C2 -C4 alkanoyl, C2 -C4 alkoxycarbonyl, C1 -C3 alkylsulfonyl, nitro or cyano, R3 is hydrogen or halogen, R4 is hydrogen, halogen or C1 -C4 alkyl and R5 is C1 -C4 alkyl or C1 -C4 haloalkyl, or R4 and R5 together are tri- or tetra-methylene, with the proviso that, when R5 is C1 -C4 haloalkyl, R1 is other than C1 -C4 haloalkyl and R2 is other than hydrogen, and when R1 is C1 -C4 haloalkyl, R2 is other than hydrogen, C1 -C4 -alkyl, C3 -C4 alkenyl, C3 -C4 alkynyl and C2 -C6 alkoxyalkyl, or of the enol ether of such a compound I wherein R1 is other than hydrogen, C1 -C4 alkyl, C3 -C4 alkynyl and C1 -C4 haloalkyl, or of a salt of such a compound wherein R1, R2 or both are hydrogen, and a formulation adjuvant.
Specification
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- Resources
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Current AssigneeCiba-Geigy Corporation (Novartis Ag)
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Original AssigneeCiba-Geigy Corporation (Novartis Ag)
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InventorsWenger, Jean, Zeller, Martin, Winternitz, Paul, Suchy, Milos
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Primary Examiner(s)Ford, John M.
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Application NumberUS07/990,826Time in Patent Office351 DaysField of Search544/311, 544/312, 544/253, 504/243, 504/240US Class Current504/243CPC Class CodesA01N 43/54 1,3-Diazines; Hydrogenated ...C07D 239/54 as doubly bound oxygen atom...C07D 239/70 condensed with carbocyclic ...C07D 239/96 Two oxygen atoms
