http://rdf.ncbi.nlm.nih.gov/pubchem/patent/AR-043518-A1

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filingDate 2004-03-09-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 2005-08-03-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber AR-043518-A1
titleOfInvention DERIVATIVES OF FTALIMIDA, PREPARATION OF THE SAME INSECTICIDES THAT UNDERSTAND THEM, THEIR MANUFACTURE AND METHODS TO COMBAT DANINE INSECTS
abstract New phthalamide derivatives insecticides of formula (1). Procedures for the preparation of such compounds, insecticidal compositions and their use for pest control. Claim 1: Phthalamide derivatives represented by the formula (1) wherein X represents H, halogen, C 1-6 alkyl, C 1-6 haloalkyl, nitro, cyano, C 1-6 alkyl sulfonyloxy, C 1-6 alkyl sulfonyloxy , phenylsulfonyloxy, (C1-6) alkyl thio-C1-6 alkyl, (C1-6) alkyl sulfinyl-C1-6 alkyl, (C1-6) alkyl sulfonyl-C1-6 alkyl, (C1-6) alkyl sulfonylamino, bis (C1-6) sulfonyl) amino or (C1-6) alkylcarbonyloxy; n represents 1, 2, 3, or 4; Y represents H, halogen, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, (C 1-6) alkyl thio, C 1-6 haloalkyl thio or cyano; m represents 1, 2, 3, or 4; R1 represents C1-8 alkyl, C1-8 alkyl which is mono- or poly-substituted with substituents selected from the group consisting of cyano, nitro, (C1-6) alkyl aminosulfonyl, N, N-di (C1-6 alkyl ) aminosulfonyl, (C1-6) alkyl sulfonylamino, N-(C1-6) sulfonyl-N-alkyl (C1-6) amino, (C1-6) alkylcarbonylamino, haloalkyl (C1-6), N-alkyl ( C1-6) carbonyl-N-alkyl (C1-6) amino, alkyl (C1-6) thiocarbonylamino, N-alkyl (C1-6) thiocarbonyl-N-alkyl (C1-6) amino, alkoxy (C1-6) imino-C1-6 alkyl, C1-6 alkyl aminocarbonyl, N, N-di (C1-6 alkyl) aminocarbonyl, C1-6 alkyl aminothiocarbonyl, N, N-di (C1-6 alkyl) aminothiocarbonyl , (C1-6) alkoxycarbonylamino, (C1-6) alkoxycarbonyl (C1-6) amino, (C1-6) alkyl aminocarbonyloxy, N, N-di (C1-6 alkyl) aminocarbonyloxy, alkoxy ( C1-6) thiocarbonylamino, (C1-6) alkoxy thiocarbonyl-(C1-6) alkyl, amino (C1-6) aminothiocarbonyloxy, N, N-di (C1-6 alkyl) aminothiocarbonyloxy, (C1-6) thiocarbonylamino , (C1-6) alkyl thiocarbonyl (C1-6) alkyl amino, (C1-6) aminocarbonylthio alkyl, N, N-di (C1-6 alkyl) aminocarbonylthio, (C1-6) alkyl thio-thiocarbonylamino, (C1-6) thio-thiocarbonyl-alkyl (C1-6) amino, (C1-6) alkylthiocarbonylthio, N , N-di (C1-6 alkyl) aminothiocarbonylthio, C3-6 cycloalkyl, C1-6 alkoxy-C1-6 alkyl, (C1-6) alkyl thio-C1-6 alkyl, (C1-6) alkyl sulfinyl- C1-6 alkyl and (C1-6) alkyl sulfonyl-C1-6 alkyl, or represents C3-8 cycloalkyl which may be substituted with substituents selected from the group consisting of C1-4 alkyl, (C1-4) alkyl thio or alkyl (C1-2) thio-C1-2 alkyl; R2 represents H or C1-6 alkyl; R3 represents H or C1-6 alkyl; A1 represents C1-8 alkylene, C1-8 haloalkylene, C2-8 alkenylene, C2-8 haloalkenylene, C2-8 alkynylene, C2-8 haloalkylene, alkylene (C1-8) amino, alkylene (C1-8) -alkyl (C1 -6) amino, (C1-8) oxy or (C1-8) thio, straight chain or branched chain alkylene; r represents 0 or 1; A2 represents C1-8 alkylene, C1-8 haloalkylene, C2-8 alkenylene, C2-8 haloalkenylene, C2-8 alkynylene or C2-8 haloalkylene, straight chain or branched chain; s represents 0 or 1; Q represents a 5- or 6-membered heterocyclic group containing from 1 to 4 heteroatoms selected from 0 to 4 atoms of N, 0 to 1 atom of O and 0 to 1 atom of S, but not containing at the same time an atom of O and an atom of S, and said heterocyclic group may have one to three> C = O, one to three> C = S, one> S = O or one> S (= O) 2 as constituents of the ring, and said heterocyclic group it may be optionally substituted with at least one or more substituents selected from the group of substituents W1 mentioned below, wherein said substituents may be identical or different, W1 represents halogen, C1-6 alkyl, C1-6 alkoxy, (C1-6 alkyl) ) thio, (C1-6) alkyl sulfinyl, alkyl (C1-6) sulfonyl, haloalkyl C1-6, haloalkoxy C1-6, haloalkyl (C1-6) thio, haloalkyl (C1-6) sulfinyl, haloalkyl (C1-6 ) sulfonyl, C3-6 cycloalkyl, (C1-6) alkyl thio-C1-6 alkyl, (C1-6) alkyl sulfinyl-C1-6 alkyl, (C1-6) alkyl sulfonyl-C1-6 alkyl; E represents phenyl, biphenyl, naphthyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, thienyl, furyl or pyrrolyl, wherein said group is optionally mono- or poly-substituted with substituents selected from group W2, wherein said substituents may be identical or different ; W2 represents halogen, nitro, C1-6 alkyl, C1-6 alkoxy, (C1-6) alkyl thio, (C1-6) alkyl sulfinyl, (C1-6) alkyl sulfonyl, C1-6 haloalkyl, C1-6 haloalkoxy, haloalkyl (C1-6) thio, haloalkyl (C1-6) sulfinyl, haloalkyl (C1-6) sulfonyl, cycloalkyl C3-6, alkyl (C1-6) thio-alkyl C1-6, alkyl (C1-6) sulfinyl- C1-6 alkyl or (C1-6) alkyl sulfonyl-C1-6 alkyl, or represents C3-5 alkylene, C3-5 haloalkylene, C2-4 oxy-alkylene, C2-4 oxy-haloalkylene, (C2-4) alkylene oxy, halo (C2-4) oxyalkyl, (C1-3) dioxy or halo (C1-3) dioxy, in case W2 is two adjacent substituents. Claim 3: Procedures for the preparation of the compounds of formula (1) according to claim 1, characterized in that (a) in the case where R2 in formula (1) represents H, compounds of formula (2) are reacted wherein R1, X and n are defined as in claim 1, with the compounds of formula (3) wherein R3, Y, m, A1, r, Q, A2, and E are defined as in claim 1, in the presence of solvents inert, or (b) in the case where R3 in formula (1) represents an atom of H, compounds of formula (4) are reacted where X, n, Y, m, A1, r, Q, A2, s and E are defined as in claim 1, with compounds of formula (5) wherein R1 and R2 are defined as in claim 1, in the presence of inert solvents and, if appropriate, in the presence of a base, or (c ) compounds of formula (6) are reacted wherein X, n, R1 and R2 are defined as in claim 1, with compounds of formula (3) wherein R3, Y, m , A1, r, Q, A2, and E are defined as in claim 1, in the presence of inert solvents, or (d) in the case where R3 in formula (1) represents an atom of H, they are reacted compounds of formula (7) wherein X, n, Y, m, A1, r, Q, A2, s and E are defined as in claim 1, with compounds of formula (5) wherein R1 and R2 are defined as in claim 1, in the presence of inert solvents, or (e) compounds of formula (8) are reacted wherein X, n, R3, Y, m, A1, r, Q, A2, s and E are defined as in the claim 1, with compounds of formula (5) wherein R1 and R2 are defined as in claim 1, in the presence of inert solvents, or (f) in the case where R1 in formula (1) represents alkyl (C1-) 6) sulfinyl-C1-6 alkyl or (C1-6) alkyl sulfonyl-C1-6 alkyl, compounds of formula (1f) are reacted wherein R1f represents (C1-6) alkyl thio-C1-6 alkyl and X, n, R2, R3, Y, m, A1, r, Q, A2, s and E are defined as in the claim tion 1, with an oxidizing agent in the presence of inert solvents.
priorityDate 2003-03-14-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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