Patent ES-8604728-A1 (ES)
Title: Quinolin-8-yloxy substd. alkanoic acid derivs.
IPC: A01N43/42
Filed: 1985-08-14
Abstract: EP--94349 A 8-Hydroxyquinoline ether derivs. of formula (I) and their acid addition salts and metal complexes are new: (R1, R2 and R3 are each H, halo, nitro, cyano, alkyl or alkoxy. R4, R5 and R6 are each H, halo or alkyl. X is an aliphatic, acyclic, satd. 1-3C hydrocarbyl. Y is carboxy (or salt); metcaptocarbonyl (or salt); carboxylic acid ester or thioester; opt. unsubstd. carboxamide; cyclised opt. substd. carboxamide deriv. or carboxylic hydrazide, or X and Y are together an opt. substd. tetrahydrofuran-2-one ring). - (I) are made e.g. by reacting a 8-hydroxyquinoline with Z.X.Y (Z is a displaceable gp.). - (I) are useful for protecting crop plants (esp. cereals) against damage caused by agricultural chemicals, particularly herbicides and specifically 2-propynyl 2-(4-(3,5-dichloropyridyl-2-oxy) phenoxy)propionate (II). They also have growth regulating activity, e.g. for increasing the yield of dicotyledons (esp. soya) and for stimulating growth of roots and germination. A typical cpd. is methyl 2-(quinolin-8-yloxy) propionate (Ia).  (/0) EPAB- EP--94349 B Use of a quinoline derivative of the formula (I), in which R1 is hydrogen, chlorine, iodine, or bromine, R2 is hydrogen, chlorine, iodine, bromine, nitro, methyl of ethyl and R3 is hydrogen or methyl, X is a methylene bridge which is unsubstituted or substituted by one or two methyl groups and Y is an oxazolin-2-yl radical, -COOR4, -COSR5, or -CONR6R7, in which R4 = hydrogen, an alkali metal cation or a quaternary ammonium cation selected from the group consisting of ammonium cation, trimethyl-, triethyl, and tri-(2-hydroxyethylene)-am monium cation; 1-18C alkyl; 1-10C alkyl, which is substituted by 1 or 2 hydroxy groups; 1-4C alkyl, which is substituted by 1 to 3 chlorine or bromine atoms, a nitro group, a cyano group, a 1-4C alkoxy group, a 2-8C alkoxy group which is interrupted by 1 or 2 oxygen atoms, a hydroxy-1-4C alkoxy group, a hydroxy 2-6C alkoxy group, which is interrupted by 1 or 2 oxygen atoms, a 1-4C alkoxycarbonyl group, a di-(1-4C alkyl)-amino group, a phenyl radical which is unsubstituted or substituted by chlorine, or methoxy, a cyclohexyl radical, a furan, tetrahydrofuran, tetrahydropyran, pyridino, piperidino or morpholino radical; 3-10C alkenyl; 3-4C alkynyl which is unsubstituted or substituted by a hydroxy group; cyclohexyl which is unsubstituted or substituted by 1 or 2 methyl groups; phenyl which is unsubstituted or substituted by 1 or 2 substituents from the group consisting of chlorine, nitro, 1-4C alkyl or methoxy; naphthyl; or pyridine; 1-12C alky; 1-4C alkyl which is substituted by a 1-4C alkoxycarbonyl group; phenyl which is unsubstituted y a chlorine atom; hydrogen; 1-18C alkyl; 2-8C alkyl, which is substituted by an amino group; 2-6C alkyl, which is substituted by a hydroxy group; 2-4C alkyl, which is substituted by a chlorine or bromine atom, a 1-4C alkylamino group, a di-(1-4C alkyl)-amino group, a 1-4C hydroxyalkylamino group, a di-(1-3C hydroxyalkyl)-amino group, a 1-4C alkoxy group, or a 1-4C alkoxycarbonyl group; 1-4C alkyl which is substituted by a cyano group or a phenyl radical which is unsubstituted or substituted by chlorine, a furanyl, tetrahydrofuranyl, piperidino or morpholino radical; 1-3C alkoxy; 3-4C alkenyl; cyclohexyl which is unsubstituted or substituted by a methyl group; phenyl which is unsubstituted or substituted by 1 or 2 substituents from the group consisting of chlorine, nitro, cyano, methyl, ethyl, methoxy and trifluoromethyl, and hydrogen; 1-6C alkyl; 1-4C alkyl which is substituted by a hydroxy group or a cyano group; 2-4C alkoxyalkyl; 3-4C alkenyl; cy  ((Dwg.0/0)) GBAB- GB2120661 B A method of protecting cultivated plants from the harmful effects of agrochemicals, which comprises treating the cultivated plants, parts of these plants or areas for growing the cultivated plants with a compound of the formula (I) in which R1, R2, and R3 independently of one another are hydrogen, halogen, nitro, cyano, alkyl or alkoxy; R4, R5 and R6 independently of one another are hydrogen, halogen or alkyl; X is an aliphatic, acyclic, saturated hydrocarbon radical having 1 to 3 carbon atoms and Y is a carboxyl group or a salt thereof, a mercaptocarbonyl group or a salt thereof, a carboxylic acid ester group, a carboxylic acid thiolester group, an unsubstituted or substituted carboxylic acid amide group, or a cyclised, unsubstituted or substituted derivative of a carboxylic acid amide group which is a substituted or unsubstituted oxazolin-2-yl radical; or X and Y together are an unsubstituted or substituted tetrahydrofuran-2-one ring, including acid addition salts and metal complexes thereof, or a composition containing one of these compounds.i USAB- US4902340 A Quinoline derivs of formula (I), their acid addn salts and metal complexes are new, where R3 is H or Cl; X is CH2 or CH(CH3); Y is C00R7 or C05R8 (where R7 is H, 1-18C alkyl, 1-10C alkyl substd by 1-3 halogens or 1 of: N02, CN, 0H, 1-8C alkoxy, 1-4C alkoxyethoxy, 2-6C hydroxyalkoxy, 2-6C hydroxyalkylthio 1-4C alkoxycarbonyl, 2-4C dialkylamino or 0Ph, or R7 is 1-6C alkyl substd by Ph, tetrahydrofuranyl, tetrahydropyranyl, furanyl, pyridinyl or phenyl substd by 1-3C alkoxy, or R7 is 3-10C alkenyl, or is 3-6C alkynyl opt substd by halogen or 0H, or is 3-8C cycloalkyl opt substd by 1-3C alkyl, or is phenyl opt substd by 1 or 2 halogen, N02, 1-4C alkyl or 1-4C alkoxy, or is naphthyl; R8 is 1-18C alkyl or is opt halo-substd phenyl. - Methallyl ester of 2-(5-chloroquinolin -8-yloxy)-acetic acid is typical. Cpds (I) are prepd eg by reaction of an 8-hydroxy-quinoline with a cpd of formula 2-x-y (where z is a leaving gp).