# US 5,707,937 A · Substituted phthalimidocinnamic acid derivatives and intermediates for their preparation

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- Number: US 5,707,937 A
- Document ID: US5707937A
- Status: Granted
- Kind: A
- Application number: 08/817,326
- Filed: 1997-04-07
- Granted: 1998-01-13
- Earliest claimed: 1994-10-28
- Assignees: BASF SE
- Inventors: Elisabeth Heistracher; Peter Plath; Christoph-Sweder von dem Bussche-Hunnefeld; Gerhard Hamprecht; Ralf Klintz; Peter Schafer; Karl-Otto Westphalen; Helmut Walter; Matthias Gerber; Ulf Misslitz
- Web page: https://patentgrep.com/patent/US5707937A

## CPC

- C07D 209/48: with oxygen atoms in positions 1 and 3, e.g. phthalimide
- A01N 37/46: N-acyl derivatives
- C07C 205/56: having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
- C07C 229/44: with carboxyl groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by unsaturated carbon chains
- C07F 7/0812: {comprising a heterocyclic ring}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

Substituted phthalimidocinnamic acid derivatives I ##STR1## wherein the variables are as defined in the description are useful as herbicides and for the desication and/or defoliation of plants.

## Claims

### Claim 1

A substituted phthalimidocinnamic acid derivative of the formula I ##STR29## where R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl;
R.sup.2 is hydrogen or halogen;
R.sup.3 is cyano, nitro, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -haloalkoxy;
R.sup.4 is hydrogen, cyano, nitro, halogen or C.sub.1 -C.sub.6 -alkyl;
R.sup.5 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -cyanoalkyl, C.sub.1 -C.sub.6 -hydroxyalkyl, C.sub.1 -C.sub.1 -mercaptoalkyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkylthio-C.sub.1 -C.sub.6 -alkyl;
R.sup.6 is one of the radicals stated under R.sup.5 or cyano, nitro, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -haloalkylthio, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkyl-C.sub.1 -C.sub.6 -alkyl, (C.sub.1 -C.sub.6 -alkoxy)carbonyl-C.sub.1 -C.sub.6 -alkyl, hydroxycarbonyl-C.sub.1 -C.sub.6 -alkyl, (C.sub.1 -C.sub.6 -alkylamino)carbonyl-C.sub.1 -C.sub.6 -alkyl, di(C.sub.1 -C.sub.6 -alkyl)aminocarbonyl-C.sub.1 -C.sub.6 -alkyl, aminocarbonyl-C.sub.1 -C.sub.6 -alkyl, (C.sub.1 -C.sub.6 -alkyl)carbonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoximino-C.sub.1 -C.sub.6 -alkyl, hydroximino-C.sub.1 -C.sub.6 -alkyl, di(C.sub.1 -C.sub.6 -alkoxy)-C.sub.1 -C.sub.6 -alkyl, di(C.sub.1 -C.sub.6 -alkylthio)-C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -haloalkenyl, (C.sub.1 -C.sub.6 -alkoxy)carbonyl, hydroxycarbonyl, (C.sub.1 -C.sub.6 -alkylamino)carbonyl, di(C.sub.1 -C.sub.6 -alkyl)aminocarbonyl, aminocarbonyl(C.sub.1 -C.sub.6 -alkyl)carbonyl, (C.sub.1 -C.sub.6 -haloalkyl)carbonyl, aryl, hetaryl, aryl-C.sub.1 -C.sub.6 -alkyl or hetaryl-C.sub.1 -C.sub.6 -alkyl, where the aryl and hetaryl rings may, optionally, carry from one to three radicals selected from the group consisting of cyano, nitro, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -haloalkylthio, hydroxyl, mercapto and (C.sub.1 -C.sub.6 -alkoxy)carbonyl;
or
R.sup.5 and R.sup.6 together form a two-membered to six-membered alkylene chain in which a methylene unit may be replaced by oxygen or C.sub.1 -C.sub.4 -alkylimino;
R.sup.7 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.2 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -cyanoalkyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.2 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkylthio-C.sub.2 -C.sub.6 -alkyl, (C.sub.1 -C.sub.6 -alkoxy)carbonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkyl-C.sub.1 -C.sub.6 -alkyl,
phenyl or benzyl, where the phenyl rings may each carry from one to three radicals selected from the group consisting of cyano, nitro, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -haloalkylthio and (C.sub.1 -C.sub.6 -alkoxy)carbonyl;
and the agriculturally useful salts of I.

### Claim 2 (depends on 1)

A substituted phthalimidocinnamic acid derivative of the formula I as claimed in claim 1, where R.sup.3 is halogen or cyano.

### Claim 3 (depends on 1)

A substituted phthalimidocinnamic acid derivative of the formula I as claimed in claim 1, where R.sup.2 is hydrogen, fluorine or chlorine.

### Claim 4 (depends on 1)

An amino- or nitrocinnamic acid derivative of the formula IIa or IIb ##STR30## where R.sup.2 to R.sup.7 and X have the meanings stated in claim 1.

### Claim 5 (depends on 1)

A herbicide containing a herbicidal amount of at least one substituted phthalimidocinnamic acid derivative of the formula I or an agriculturally useful salt of I, as claimed in claim 1, and at least one inert liquid or solid carrier and, optionally, at least one surfactant.

### Claim 6 (depends on 1)

A plant desiccant or defoliant containing an amount, effective for desiccation or defoliation, of at least one substituted phthalimidocinnamic acid derivative of the formula I or an agriculturally useful salt of I, as claimed in claim 1, and at least one inert liquid or solid carrier and, optionally, at least one surfactant.

### Claim 7 (depends on 1)

A process for the preparation of a herbicide, wherein a herbicidal amount of at least one substituted phthalimidocinnamic acid derivative of the formula I or an agriculturally useful salt of I, as claimed in claim 1, and at least one inert liquid or solid carrier and, optionally, at least one surfactant are mixed.

### Claim 8 (depends on 1)

A process for the preparation of a desiccant or defoliant, wherein an amount, effective for desiccation or defoliation, of at least one substituted phthalimidocinnamic acid derivative of the formula I or an agriculturally useful salt of I, as claimed in claim 1, and at least one inert liquid or solid carrier and, optionally, at least one surfactant are mixed.

### Claim 9 (depends on 1)

A method for controlling undesirable plant growth, wherein a herbicidal amount of at least one substituted phthalimidocinnamic acid derivative of the formula I or one agriculturally useful salt of I, as claimed in claim 1, is allowed to act on plants or their habitat or on seed.

### Claim 10 (depends on 1)

A method for the desiccation or defoliation of plants, wherein an amount, effective for desiccation or defoliation, of at least one substituted phthalimidocinnamic acid derivative of the formula I or one agriculturally useful salt of I, as claimed in claim 1, is allowed to act on plants.

### Claim 11 (depends on 1)

A process for the preparation of a substituted phthalimidocinnamic acid derivative of the formula I as claimed in claim 1, where R.sup.4 is chlorine or bromine, wherein an aniline of the formula III ##STR31## and a propynoic acid derivative IV ##STR32## are subjected to a Meerwein alkylation reaction.

### Claim 12 (depends on 1)

A process for the preparation of a substituted phthalimidocinnamic acid derivative of the formula I as claimed in claim 1, wherein a benzaldehyde of the formula V ##STR33## is reacted with an ylide of the formula VI ##STR34## where Ar is an aromatic radical which, if desired, may be substituted.

### Claim 13 (depends on 1)

A process for the preparation of a substituted phthalimidocinnamic acid derivative of the formula I as claimed in claim 1, where R.sup.4 is nitro or cyano, wherein a benzaldehyde of the formula V ##STR35## is reacted with a CH-acidic compound of the formula VII ##STR36##

### Claim 14 (depends on 1)

A process for the preparation of a substituted phthalimidocinnamic acid derivative of the formula I as claimed in claim 1, wherein either an activated carboxylic acid of the formula VIII ##STR37## where L.sup.1 is a conventional leaving group, is reacted with a nucleophile of the formula IX ##STR38## or an activated carboxylic acid of the formula X ##STR39## is reacted with an alkohol HOR.sup.7.

### Claim 15 (depends on 1)

A process for the preparation of a substituted phthalimidocinnamic acid derivative of the formula I as claimed in claim 1, wherein either an acid derivative XII ##STR40## is reacted with an alkylating agent XIII ##STR41## where L.sup.2 is a conventional leaving group, or a compound I as claimed in claim 1, where R.sup.7 is hydrogen, is reacted with an alkylating agent L.sup.2 R.sup.7.

### Claim 16 (depends on 1)

A process for the preparation of a substituted phthalimidocinnamic acid derivative of the formula I as claimed in claim 1, wherein a tetrahydrophthalic anhydride of the formula XIV ##STR42## is reacted with an aminocinnamic acid derivative IIa ##STR43##

### Claim 17 (depends on 4)

A process for the preparation of a nitrocinnamic acid derivative of the formula IIb as claimed in claim 4, wherein a correspondingly substituted aminocinnamic acid derivative IIa is reduced.