Phthalimides useful as intermediate compounds

• US 5,508,412 A
• Filed: 07/27/1995
• Issued: 04/16/1996
• Est. Priority Date: 10/19/1990
• Status: Expired due to Fees

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: BASF AG (BASF SE)
• Inventors: Walter, Helmut, Westphalen, Karl-Otto, Misslitz, Ulf, Gerber, Matthias, Meyer, Norbert, Harreus, Albrecht, Rang, Harald, Kast, Juergen
• Primary Examiner(s): Haley, Jacqueline
• Application Number:
  US08/508,044
• Time in Patent Office: 264 Days
• Field of Search: 546/272, 548/475
• US Class Current: 546/277.1
• CPC Class Codes: A01N 35/10 containing a carbon-to-nitrogen double bond
• CPC Class Codes: A01N 43/14 six-membered rings
• CPC Class Codes: A01N 49/00 Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group , wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group , wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof containing hydrocarbons A01N27/00
• CPC Class Codes: C07C 239/20 having oxygen atoms of hydroxylamino groups etherified
• CPC Class Codes: C07C 251/42 with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a ring other than a six-membered aromatic ring
• CPC Class Codes: C07C 251/52 of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
• CPC Class Codes: C07C 2601/02 with a three-membered ring
• CPC Class Codes: C07C 2601/08 the ring being saturated
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 2601/16 the ring being unsaturated
• CPC Class Codes: C07C 317/28 with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
• CPC Class Codes: C07C 323/47 to oxygen atoms
• CPC Class Codes: C07D 213/30 Oxygen atoms
• CPC Class Codes: C07D 261/08 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 307/12 Radicals substituted by oxygen atoms
• CPC Class Codes: C07D 309/06 Radicals substituted by oxygen atoms
• CPC Class Codes: C07D 309/22 Radicals substituted by oxygen atoms
• CPC Class Codes: C07D 309/28 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 317/26 Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
• CPC Class Codes: C07D 333/22 Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
• CPC Class Codes: C07D 339/06 : having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
• CPC Class Codes: C07D 405/12 : linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 409/12 : linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 413/10 : linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 413/12 : linked by a chain containing hetero atoms as chain links

Abstract

Unsaturated cyclohexenone oxime ethers I ##STR1## (Q═H, alkylcarbonyl, benzoyl, alkali metal or alkaline earth metal ion, substituted or unsubstituted ammonium ion, phosphonium ion, sulfonium ion, sulfoxonium ion, an equivalent of a transition metal cation;

W=--C.tbd.C-- or --CH═CH--;

R¹ =substituted or unsubstituted cycloalkyl, cycloalkenyl or 6-membered heterocyclic group which has 1-2 oxygen and/or sulfur atoms and can be saturated or partially unsaturated; substituted or unsubstituted 5-membered saturated heterocycle with 1-2 oxygen and/or sulfur atoms; substituted or unsubstituted 5-membered heteroaromatic group with 1-2 nitrogen atoms and/or 1 oxygen or sulfur atom; substituted or unsubstituted phenyl, pyridyl or R⁹ -X-substituted alkyl with X=O, S, --SO--, --SO₂ -- and R⁹ =alkyl, phenyl, 5/6-membered hetaryl with 1-3 hetero atoms;

R² =alkyl;

R³ =H, alkyl;

R⁴ =H, halogen, alkyl;

R⁵ =H, alkyl;

or R³ +R⁴, R³ +R⁵ or R⁴ +R⁵ together form C₂ -C₄ -alkylene or C₂ -C₄ -alkenylene;

R⁶ =H, alkyl, unsubstituted or phenyl-substituted haloalkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, substituted or unsubstituted cycloalkyl or cycloalkenyl; substituted or unsubstituted phenyl or pyridyl) are suitable as herbicides.

Claims

1. A phthalimide of the formula IX ##STR206## where R³

is hydrogen or C₁ -C₆ -alkyl;

R⁴

is hydrogen, halogen or C₁ -C₆ -alkyl;

R⁵

is hydrogen or C₁ -C₆ -alkyl;

or R³ and R⁴, R³ and R⁵ or R⁴ and R⁵ together may form C₂ -C₄ -alkylene or C₂ -C₄ -alkenylene;

R⁶

is hydrogen, C₁ -C₆ -alkyl, partially or completely halogenated C₁ -C₄ -alkyl which may be optionally substituted by a phenyl radical, or C₂ -C₆ -alkenyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, C₃ -C₇ -cycloalkyl or C₅ -C₇ -cycloalkenyl, wherein the C₃ -C₇ -cycloalkyl and C₅ -C₇ -cycloalkenyl may be optionally substituted by one to three of the following;

hydroxyl, C₁ -C₄ -alkyl, partially or completely halogenated C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl or C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl;

phenyl or pyridyl, both of which may be optionally substituted by one to three of the-following;

nitro, cyano, hydroxyl, halogen, C₁ -C₄ -alkyl, partially or completely halogenated C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, partially or completely halogenated C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl or C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl.

2. A phthalimide of the formula IX as claimed in claim 1, where R³, R⁴ and R⁵ are hydrogen.