Oximethers and fungicides containing them

    公开(公告)号:GR3019748T3

    公开(公告)日:1996-07-31

    申请号:GR960401145

    申请日:1996-04-24

    Applicant: BASF AG

    Abstract: alpha -Imino oxime cpds, described as oxime ethers, of formula (I) are new: R = CR2R3R4 or opt. substd. 3-8C cycloalkyl, 2-8C alkenyl, 2-8C alkynyl, phenyl or heteroaryl; R1 = H or 1-8C alkyl; R2 = H, 1-8C alkyl, aralkyl, heteroarylalkyl, alkoxyalkyl, aryloxyalkyl, aryl or heteroaryl; R3 = H, Me, CN, COOH or 2-9C alkoxycarbonyl; R4 = a gp. as defined for R2; or CR2R3 is a 5- to 8-membered lactone ring or CR2R4 is a 3-8C cycloalkane ring; R5 = H, 1-8C alkyl, aralkyl, 3-6C cycloalkyl, OH, 1-4C alkoxy, NH2, 1-4C alkylamino or dialkylamino; Y = a gp. stated to be an opt. substd. 1-8C alkyl, opt. substd. 2-8C alkenyl, 2-8C alkynyl, O, S(O)m (m = 0-2), N substd. by opt. substd. 1-8C alkyl, oxycarbonyl, carbonyloxy, oxycarbonyl (1-8C) alkyl, carbonyloxy (1-8C) alkyl, 2-8C oxyalkyloxy, 2-8C oxyalkenyl, 1-8C alkoxy, 1-4C oxyalkyl, 1-8C thioalkyl, azo, opt. 1-8C alkyl-substd. -carbonylamino, -aminocarbonyl or -aminocarbonyloxy, oxyimino or opt. substd. imino oxyalkyl; Z = (a) 1-18C alkyl, 2-18C alkenyl, 3-18C alkynyl, aryl, aryl (1-10C) alkyl, aryl (2-10C) alkenyl, aryloxy (1-10C) alkyl, (1-4C) alkoxy (1-10C) alkyl, 1-10C haloalkyl, 2-5C alkoxycarbonyl or heteroaryl; (b) aryloxy, aryloxy (1-10C) alkoxy, aryl (1-10C) alkoxy, 1-10C alkoxy or heteroaryloxy when Y is not oxyalkyl, oxyalkyloxy, thialkyl (sic), -O-N=C- (sic), -N=N-, oxycarbonyl, oxycarbonyloxy, O or S; or (c) 1-18C alkylthio or arylthio when Y is not oxyalkyl, oxyalkyloxy, -O-N=C- (sic), -N=N-, oxycarbonyl, oxycarbonyloxy or O, and Z is opt. substd. by halogen, CN, NO2, 1-4C alkyl, 2-4C alkenyl, 1-4C alkoxy, 1-4C haloalkyl, (1-4C) alkoxy (1-4C) alkyl, di(1-4C) alkoxy (1-4C) alkyl, opt. substd. 1-10C alkoxyimino, opt. substd. 2-10C alkenyloxyimino, opt. substd. aralkoxyimino, opt. substd. 2-10C alkanoyl, opt. substd. formyl, 2-4C haloalkenyl, 2-5C alkoxycarbonyl, opt. substd. phenyl, or opt. substd. 5-membered heterocyclyl which contains 1-4 heteroatoms (N, O and/or S) and is opt. fused with an opt. substd. aromatic or heteroaromatic ring; X = H, halogen, NO2 and/or opt. substd. 1-4C alkyl, 1-4C alkoxy and/or 1-4C haloalkyl; m = 1-4.

    Prepn. of E-oxime ether(s) of phenyl-glyoxylic acid ester(s)

    公开(公告)号:DE4042272A1

    公开(公告)日:1992-07-02

    申请号:DE4042272

    申请日:1990-12-31

    Applicant: BASF AG

    Abstract: Prepn. of E-oxime-ethers of phenylglyoxylic acid esters of formula (I) comprises (a) reacting a phenol Xm-Ph-PH in a base in the presence of a solvent to give a phenolate; (b) mixing with a lactone of formula (III); (c) distilling off solvent and reacting the mixt. at 50-250 deg.C in the melt; (d) washing with water and acid to give a 2-phenoxymethylbenzoic acid of formula (IV); Q = OH); (e) treating with phosgene or SOCl2 to give the 2-phenoxymethylbenzoyl chloride (IV; Q = Cl); (f) reacting with alkali(ne earth)metal cyanide opt. in the presence of prussic acid; (g) treating the 2-phenoxymethylbenzoyl cyanide (IV; Q = CN) with MeOH in the presence of acid to give (VIIb); (h) opt. splitting under acidic conditions to give (IV; Q = C(O)NHR) or (i) treating (IV; Q=R) with dimethyl sulphoxide in the presence of a base to give a beta ketosulphoxide (IV; Q = CH2SOCH3) and treating with a halogenating agent, and MeOH in acid to give (IV; Q = C(O)OMe); (k) reacting (IV; Q = C(O)OMe) and/or (VIIb) with O-methylhydroxylamine or its acid addn. salt to give (I). Q = R1CH2SOMe, OH, Cl, CN or C(O)NNR; X, Y = halo, 1-4C alkyl, 1-4C alkoxy or CF3; m = 0-4; n = 0-3; R = 1-4C alkyl.

    Prepn. of E-oxime ether(s) of phenyl-glyoxylic acid ester(s)

    公开(公告)号:DE4042271A1

    公开(公告)日:1992-07-02

    申请号:DE4042271

    申请日:1990-12-31

    Applicant: BASF AG

    Abstract: Prepn. of E-oxime-ethers of phenylglyoxylic acid esters of formula (I) comprises (a) reacting a phenol Xm-Ph-PH in a base in the presence of a solvent to give a phenolate; (b) mixing with a lactone of formula (III); (c) distilling off solvent and reacting the mixt. at 50-250 deg.C in the melt; (d) washing with water and acid to give a 2-phenoxymethylbenzoic acid of formula (IV); Q = OH); (e) treating with phosgene or SOCl2 to give the 2-phenoxymethylbenzoyl chloride (IV; Q = Cl); (f) reacting with alkali(ne earth)metal cyanide opt. in the presence of prussic acid; (g) treating the 2-phenoxymethylbenzoyl cyanide (IV; Q = CN) with MeOH in the presence of acid to give (VIIb); (h) opt. splitting under acidic conditions to give (IV; Q = C(O)NHR) or (i) treating (IV; Q=R) with dimethyl sulphoxide in the presence of a base to give a beta ketosulphoxide (IV; Q = CH2SOCH3) and treating with a halogenating agent, and MeOH in acid to give (IV; Q = C(O)OMe); (k) reacting (IV; Q = C(O)OMe) and/or (VIIb) with O-methylhydroxylamine or its acid addn. salt to give (I). Q = R1CH2SOMe, OH, Cl, CN or C(O)NNR; X, Y = halo, 1-4C alkyl, 1-4C alkoxy or CF3; m = 0-4; n = 0-3; R = 1-4C alkyl.

    Process for preparing isomers of alpha-bis-oximes

    公开(公告)号:CZ288053B6

    公开(公告)日:2001-04-11

    申请号:CZ315597

    申请日:1996-03-25

    Applicant: BASF AG

    Abstract: In the present invention there is disclosed a process for preparing of alpha-bis-oxime isomers of the general formula Ia: Re1O-N=CRe2-CRe3=N-ORe4 (Ia), wherein the groups Re1O- and Re2 on the N=C bond are in mutual position cis and wherein Re1 represents alkyl containing 1 to 6 carbon atoms, alkenyl containing 3 to 6 carbon atoms and alkynyl having 3 to 6 carbon atoms, Re2 represents an optionally substituted phenyl or an optionally substituted hetaryl, Re3 represents a hydrogen atom, a cyano group, a halogen atom, alkyl containing 1 to 4 carbon atoms, haloalkyl containing 1 to 4 carbon atoms and cycloalkyl having 3 to 6 carbon atoms and Re4 represents hydrogen. The proposed preparation process is characterized in that {alpha}-bis-oxime isomer of the general formula Ib: Re1O-N=CRe2-CRe3=N-ORe4 (Ib), wherein the groups Re1O- and Re2 on the N=C bond are in mutual position trans and wherein Re1, Re2, Re3 and Re4 are as specified above, optionally in a mixture with the {alpha}-bis-oxime isomer of the general formula Ia: Re1O-N=CRe2-CRe3=N-ORe4 (Ia) is treated in an aromatic hydrocarbon with a Lewis acid.

    47.
    发明专利
    未知

    公开(公告)号:ES2104988T3

    公开(公告)日:1997-10-16

    申请号:ES93105432

    申请日:1993-04-01

    Applicant: BASF AG

    Abstract: Process for the preparation of an o-iminooxymethylbenzoic acid of the general formula I in which m denotes an integer from 0 to 3, X denotes alkyl, alkoxy, nitro, cyano, or halogen, R1 and R2 denote hydrogen, cyano, hydroxyl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, benzylthio, benzylamino, alkylcarbonyl, optionally substituted phenylcarbonyl, optionally substituted benzylcarbonyl, alkoxycarbonyl, optionally substituted phenoxycarbonyl, optionally substituted benzyloxycarbonyl, optionally substituted aryl, optionally substituted aryloxy, optionally substituted arylthio, optionally substituted arylalkyl, optionally substituted arylalkenyl, optionally substituted aryloxyalkyl, optionally substituted arylthioalkyl, optionally substituted hetaryl, optionally substituted hetaryloxy, optionally substituted hetarylthio, optionally substituted heteroarylalkyl, optionally substituted hetarylalkenyl, optionally substituted hetaryloxyalkyl, hetarylthioalkyl, optionally substituted heterocyclyl, optionally substituted heterocyclyloxy, or denote N(R )2, where R denotes H, alkyl or phenyl, or denote -CO-N(R )2, where R denotes H, alkyl or phenyl, or R and R together with the C atom which they substitute can form a carbo- or heterocyclic ring, or R or R denotes halogen or the group denotes the radical where n denotes the integers 1 to 4 and the radicals R denote H, halogen, cyano, nitro; alkyl, alkoxy, aryl, aryloxy, benzyloxy, hetaryl and hetaryloxy, by reacting an oxime of the general formula II in which R1 and R2 have the abovementioned meanings, with a lactone of the general formula III in which X and m have the abovementioned meaning, if appropriate in the presence of a base or of a diluent, and o-iminooxymethylbenzoic acids of the abovementioned formula.

    49.
    发明专利
    未知

    公开(公告)号:DK0564984T3

    公开(公告)日:1997-09-15

    申请号:DK93105432

    申请日:1993-04-01

    Applicant: BASF AG

    Abstract: Process for the preparation of an o-iminooxymethylbenzoic acid of the general formula I in which m denotes an integer from 0 to 3, X denotes alkyl, alkoxy, nitro, cyano, or halogen, R1 and R2 denote hydrogen, cyano, hydroxyl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, benzylthio, benzylamino, alkylcarbonyl, optionally substituted phenylcarbonyl, optionally substituted benzylcarbonyl, alkoxycarbonyl, optionally substituted phenoxycarbonyl, optionally substituted benzyloxycarbonyl, optionally substituted aryl, optionally substituted aryloxy, optionally substituted arylthio, optionally substituted arylalkyl, optionally substituted arylalkenyl, optionally substituted aryloxyalkyl, optionally substituted arylthioalkyl, optionally substituted hetaryl, optionally substituted hetaryloxy, optionally substituted hetarylthio, optionally substituted heteroarylalkyl, optionally substituted hetarylalkenyl, optionally substituted hetaryloxyalkyl, hetarylthioalkyl, optionally substituted heterocyclyl, optionally substituted heterocyclyloxy, or denote N(R )2, where R denotes H, alkyl or phenyl, or denote -CO-N(R )2, where R denotes H, alkyl or phenyl, or R and R together with the C atom which they substitute can form a carbo- or heterocyclic ring, or R or R denotes halogen or the group denotes the radical where n denotes the integers 1 to 4 and the radicals R denote H, halogen, cyano, nitro; alkyl, alkoxy, aryl, aryloxy, benzyloxy, hetaryl and hetaryloxy, by reacting an oxime of the general formula II in which R1 and R2 have the abovementioned meanings, with a lactone of the general formula III in which X and m have the abovementioned meaning, if appropriate in the presence of a base or of a diluent, and o-iminooxymethylbenzoic acids of the abovementioned formula.

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