CA1214780A

CA1214780A - N-acylanthranilic acid derivatives, a process for their manufacture, and their use for controlling undesirable plant growth

Info

Publication number: CA1214780A
Application number: CA000448940A
Authority: CA
Inventors: Gerhard Hamprecht; Wolfgang Rohr; Juergen Varwig; Bruno Wuerzer
Original assignee: BASF SE
Current assignee: BASF SE
Priority date: 1983-03-09
Filing date: 1984-03-06
Publication date: 1986-12-02
Also published as: BR8401051A; EP0120352A1; EP0120352B1; DE3308239A1; DE3482469D1; ZA841726B; HU190948B

Abstract

ABSTRACT OF THE DISCLOSURE:

This invention relates to novel N-acylanthranilic acid derivative of the formula

Description

121478~

The present invention relates to N-aclyanthranilic acid derivatives, a process for their manufacture, herbici-des with contain these derivatives as active ingredients, and a method of controlling undesirable plant growth using these compounds.
It has been disclosed that substituted N-acyl-anthranilic acid derivatives are intermediates for the synthesis of pharmacological and herbicidal compounds (French Patent 2,121,341 and German Laid-Open Applications DOS 2,914,915, DOS 3,000,309 and DOS 3,037,970), herbicidal active ingredients (Belgian Patent 648,259) or fungicidal active ingredients (DOS 2,759,121).
It has now been found that N-acylanthranilic acid derivatives of the formula I

Rl y ~ C-Y'-R (I) NH-~-R2 where R1 is halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy, C~-C4-haloalkyl, C1-C4-haloalkoxy or C1-C4-haloalkylmercapto, R is unsubstituted or C1-C4-alkyl-substituted thienyl or is phenyl which is m-substituted, p-substituted or m- and p-substituted by C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-haloalkylmercapto, C1-C4-haloalkylsulfinyl, C1-C4-halo-alkylsulfonyl or C1-C4-alkylsulfonyl, R is a straight-chain or branched alkyl, alkenyl, or alkynyl radical of not more than 12 carbon atoms which is unsubstituted or substi-tuted by halogen, cyano, thiocyano, nitro, C2-C4-alkyl-carbonyl C -C -alkoxy, C2-C4- -~*
,~ . ..

~2~7~

- 2 - ~.Z. 0050/36410 a~kenY~OXY~ C2-C4-a~kYnY~OXY, Cl-c4-a~kylmercapto~
Cz-C4-alkenylnercapto, C2-C4-alkynylmercapto, C2-C5-alkoxycarbonyl, C2-C5-a~kylmercaptocarbonyl or C3-C4-a~kenylcarbonyl, or is C3-C7-cyc~oa~ky~ wh;ch is unsub-stituted or substituted by C1-C4-alkyl, C1-C4-alkoxy, C1-C4-a~ky~mercapto, C1-C4-alkylsulfonyl, halogen, tr~fluoromethy~, n~tro or cyano, a 2-~2-alkoxyethoxy)-ethyl, 2-~2-a~kenoxyethoxy)-ethyl or 2-~2-alkynoxyethoxy)-ethyl radical of not more than 8 carbon atoms, a 3-(2-alkoxyethoxy)-n-propy~ radical of not more than 9 carbon atoms, phenyl ~hich is unsubstituted or substituted by halogen, C1-C4-a~kYl~ C1~C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylmercapto, C1-C4-halo-alkylmercapto, nitro or cyano, or ;s phenoxyalkyl of 7 to 12 carbon atoms, phenoxyalkenyl of 8 to 12 carbon atoms, phenoxyalkynyl of 8 to 12 carbon atoms or phenylalkyl of 7 to 12 carbon atoms, each of which is unsubstituted or substituted by halogen, C1-C4-alkyl, C1-C4-h~loalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylmercapto, C1-C4-haloalkylmercapto, nitro or cyano, and Y and Y' are each oxygen or sulfur, ~ith the prov;so that R2 may fur-thermore be unsubstituted or halogen-substitutet phenyl if R1 is fluorine, are very ~ell tolerated by crops and have a more powerful herb;c1dal action than conven-tional herbicidal N-acylanthrani~;c ac;d der;vat;ves.
In formula ~, R1 is, for example, halo-g n, n;tro, C1 C4 alkyl, C1-C4-alkoxy, C1-C4-halo-alkyl, Ct-C4-haloalkoxy or C1-C4-haloalkyLmercapto, eg. 'luorine, chlor;ne, brom;ne, iod;ne, nitro, methyl, ethyl, isopropyl, n-propyl, ;sobutyl, tert.-butyl, tr;-chloromethyl, difluorochloromethyl, trif~uoromethyl, di-fluoromethyl, Z,2,1,1-tetrafluoroethyl, methoxy, ethoxy, isopropoxy, n-butoxy, trifluoromethoxy, hexafluoroisoprop-oxy, difluoromethy~mercapto or trifluoromethylmercapto, or a radical of the formula Y"-Cf2CtZ~3, where Y" is oxy-gen or su~fur and the radicals Z independentl~ of one ano-ther are each hydrogen, fluorine, chlorine, bromine or ~, .

7~(i iodine, eg. 2,2,1,1-tetrafluoroethoxy, l,1-difluoroethoxy, 2,2,1,1-tetrafluoroethylmercapto or 1,1-difluoroethyl-mercapto.
In formula I, R is, for example, thien-3-yl or thien-2-yl which is unsubstituted or substituted by C1-C4-alkyl, preferably by methyl, or is aryl, eg. phenyl or naphthyl, in particular phenyl, which may carry the following substituents in the m-, p- or m- and p-position:
4 Y ~ 1 C4-haloalkoxy, Cl-C4-haloalkyl Cl-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, halogen or C1-C4-alkylsulfonyl, such as methylmercapto, ethyl-mercapto, isopropylmercapto, chloromethoxy, fluoromethoxy, difluoromethoxy, difluorochloromethoxy, trifluoromethoxy, trichloromethoxy, 1,1,2,2-tetrafluoroethoxy, 1,1,2,2-trifluoro-2-chloroethoxy, 1,1,1,-trifluoro-2-bromoethoxy, 1,1,2,3,3,3-hexafluoro-n-propyloxy, pentafluoroethoxy, hexafluoroisopropoxy, difluoromethylmercapto, trifluoro-methylmercapto, pentafluoroethylmercapto, 1,1,2,2-tetra-fluoroethylmercapto, trichloromethylmercapto, dichloro-fluoromethylmercapto, trifluoromethylmercapto, methyl-sulfonyl, ethylsulfonyl, isopropylsulfonyl, trifluoro-methylsulfonyl, pentafluoroethylsulfonyl, trifluoromethyl-sulfinyl, fluorine, chlorine, bromine, iodine, trifluoro-methyl, difluorochloromethyl, difluoromethyl, 1,1,2,2-tetrafluoroethyl or pentafluoroethyl.
In formula I, R is, for example, a straight-chain or branched alkyl, alkenyl or alkynyl radical of not more than 12, preferably not more than 4, carbon atoms, which is unsubstituted or substituted by halogen, cyano, thiocyano, nitro, C2-C4-alkylcarbonyl, Cl-C4-alkoxy, =

" r ~1 lzl~7sa - 4 - O.z. 0050/36410 C2-C4-alkenyloxy, C2-C4-alkynyLoxy, C1-C4-alkyl-mercapto, C2-C4-alkenylmercapto, C2-C4-alkynylmer-capto, C2-C5-alkoxycarbonyl, C2-Cs-alkylmercapto-carbonyl or C3- or C4-alkenylcarbonyl, e~ methyl, ethyl, n-propyl, ;sopropy~, n-butyl, ;sobutyl, sec.-butyl, tert.-butyl, n-pentyl, tert.-amyl, n-hexyl, pent-3-yl, 1,2-d;-methyl-n-propyl, 1,3-d;methyl-n-buty~, 1-ethyl-2-methyl-n-propyl, 1,2,2-trimethyl-n-propy~, 1,2-d;methyl-n-hex-4-yl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, allyl, methallyl, crotyl, 2-ethyl-hex-2-enyl, hex-5-enyl, Z-methyl-but-2-enyl, 2-methyl-but-3-enyl, but-1-en-3-yl, 2-methyl-but-1-en-4-yl, 2-methyl-but-Z-en-4-yl, 3-methyl-but-1-en-3-yl, propargyl, but-1-yn-3-yl, but-2-ynyl, 2-chloroethyl, 2-chloro-n-propyl, 3-chloro-n-propyl, 2-chloro-sec.-butyl, Z-chloro;sobutyl, 2-fluoro-sec.-butyl, 2-fluoro-;sobutyl, 2-fluoro;sopropyl, chloro-tert.-butyl, 2,2,2-trifluoroethyl, Z-cyanoethyl, 2-cyano-n-propyl, 3-cyano-n-propyl~ 4-cyano-n-butyl, 3-cyano-prop-2-enyl, 4-cyano-but-Z-ynyl, 2-nitroethyl, 2-n;tro-n-propyl, 3-nitro-n-propyl, 3-n;tro-prop-2-enyl, propan-2-onyl, butan-2-onyl, but-3-en-2-onyl, methoxyethyl, ethoxyethyl, 3-methoxy-propyl, methoxy;sopropyl, 3-methoxybutyl, 1-methoxybut-2-yl, ethoxy-tert.-butyl, methoxy-tert.-butyl, 2-methoxy-n-butyl, 4-methoxy-n-butyl, 2-allyloxyethyl, 2-propargyloxy-Z5 ethyl~ 2-a~lyloxy-n-propyl, 2-propargyloxy-n-propyl, 3-allyloxy-n-propyl, 4-allyloxy-but-2-ynyl, 2-methylmercapto-ethyl, 2-ethylmercaptoethyl, 3-methylmercapto-n-propyl, 2-allylmercaptoethyl, 2-propargylmercaptoethyl, 2-allyl-mercapto-n-propyl, vinylcarbonylethyl, 2-thiocyanoethyl, 2-th;ocyano-n-propyl, 3-th;ocyano-n-propyl, 4-th;ocyano-n-butyl, 3-methoxycarbonyl-prop-2-yl, 3-ethoxycarbonyl-prop-2-yl, 3-methylmercaptocarbonyl-prop-2-yl, 3-ethyl-mercaptocarbonyl-prop-2-yl, 3-methoxycarbonyl-prop-Z-enyl,

3-ethoxycarbonyl-prop-2-enyl, 3-ethoxycarbonyl-prop-2-ynyl or 3-n~butoxycarbonyl-prop-2-ynyl, or is C3-C7-cyclo-alkyl which is unsubstituted or substituted by C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylmercapto, C2-C4-121478~

- 5 - ~.z. 0050/36410 alkylsulfonyl, halogen, trifluoromethyl, nitro or cyano, eg. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 2- or 3-methylcyclopentyl, 2-, 3- or 4-methylo cyclohexyl, 2~, 3- or 4-methoxycyclohexyl, 2-~ 3- or 4-methylmercaptocyclohexyl, 2-, 3- or 4-methylsulfonylhexyl, 2-, 3- or 4-chlorocyclohexyl, 2-, 3- or 4-trifluoromethyl-cyclohexyl, 2-, 3- or 4-nitrocyclohexyl or 2-, 3- or 4-cyanocyclohexyl, or is a 2-~2-alkoxyethoxy)-ethyl, 2-t2-alkenoxyethoxy)-ethyl or 2-~2-alkynoxyethoxy)-ethyl radi-cal of not more than 8 carbon atoms, eg. 2-(2-methoxy-ethoxy)-ethyl, 2-~2-al~yloxyethoxy)-ethyl or 2-~2-propar-gyloxyetho%y~-ethyl, or a 3-~2-alkoxyethoxy)-n-propyl rad;cal of not more than 9 carbon atoms, eg. 3-(2-methoxy-ethoxy)-n-propyl or is phenyl ~hich is unsubstituted or subst;tuted by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylmer-cap~o, C1-C4-haloalkylmercapto, n;tro or cyano, or is phenoxyalkyl of 7 to 12 carbon atoms, phenoxyalkenyl of 8 to 12 carbon atoms, phenoxyalkynyl of 8 to 12 carbon atoms or phenylalkyl of 7 to 12 carbon atoms, each of which is unsubstituted or subst;tuted by halogen, C1-C4-alkyl, C1-C4-haloalky~, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylmercapto, C1-C4-haloalkylmercapto, n;tro or cyano, eg. phenyl, 2-, 3- or 4-chlorophenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,5- or 3,6-d;chlorophenyl, 2,4,5- or 2,4,6-tr;chlorophenyl, 2-, 3^ or 4-cresyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,5- or 3,6-dimethylphenyl, 2-chloro-4-trifluoromethyl-phenyl, 2-, 3- or 4-trifluoromethylphenyl, 2-, 3- or 4-n;trophenyl, 2,4-d;n;trophenyl, Z-chloro-4-nitrophenyl, 2-nitro-4-chlorophenyl, 2-, 3- or 4-cyanophenyl, 2-chloro-

4-cyanophenyl, 2-cyano-4-n;trophenyl, 2-, 3- or 4-methoxy-phenyl, 2-, 3- or 4-chlorodifluoromethoxyphenyl, 2-, 3-or 4-methylmercaptophenyl, 2-, 3- or 4-trifluoromethyl-mercaptophenyl, 2-~2'-, 3'- or 4C-chlorophenyl)-ethyl~
2-(2',4'-dichlorophenyl)-ethyl, 2-(2',4',6'-trichloro-phenyl)-ethyl, 2-(3',5'-dichlorophenyl)-ethyl, 2-(o-, m-or p-tolyl)-ethyl, 2-(3',4'-xylyl)-ethyl, 2-(2'-, 3'- or ~Z1478~

4'-trifluoromethylphenyl)-ethyl, 2-(o-, m- or p-anisyl)-ethyl, 2-(o-, m- or p-difluoromethoxyphenyl)-ethyl, 2-(o-, m- or p-chlorodifluoromethoxyphenyl)-ethyl, 2-(o-, m- or p-methylmercaptophenyl)-ethyl, 2-(o-, m- or p-trifluoro-methylmercaptophenyl)-ethyl, 2-(o-, m- or p-cyanophenyl)-ethyl, 2-(0-, m- or p-thiocyanatophenyl)-ethyl, 3-(o-, m-or p-chlorophenylO-n-propyl, 3-(o-, m- or p-trifluoro-methylphenyl)-n-propyl, 2-phenylethyl, 3-phenyl-n-propyl, 4-phenyl-n-butyl, 5-phenyl-n-pentyl, 2-(o-, m- or p-nitro-phenyl)-ethyl, 2-(3'-chloro-4'-methoxyphenyl)-ethyl, 2-(4'-chloro-3'-methocyphenyl)-ethyl, 2-(2'-chloro-4'-tri-fluoromethylphenyl)-ethyl, 2-phenoxy-ethyl, 3-phenoxy-n-propyl, 4-phenoxy-n-butyl, 2-(o-, m- or p-chlorophenoxy)-ethyl, 2-(2',4'-dichlorophenoxy)-ethyl, 2-(o-, m- or p-cresyloxy)-ethyl, 2-(o-, m- or p-trifluoromethylphenoxy)-ethyl, 2-(2'-chloro-4'-trifluoromethylphenoxy)-ethyl, 3-(o-, m- or p-chlorophenoxy)-n-propyl, 4-phenoxy-but-2-ynyl, 4-(p-chlorophenoxy)-butyn-2-yl, 4-phenoxy-but-2-enyl, 3-(2',4'-dichlorophenoxy)-n-propyl, 3-(3'-trifluoromethyl-phenoxy)-n-propyl or 4-(p-chlorophenoxy)-but-2-enyl.
R2 may furthermore be unsubstituted or halogen-substituted phenyl, if R1 is fluorine. Examples of appropriate radicals are phenyl, 3-fluorophenyl, 4-fluoro-phenyl, 3-chlorophenyl, 4-chlorophenyl, 3-bromophenyl and 4-iodophenyl.
Preferred compounds of the formula I are those in which Rl is halogen, R2 is a phenyl radical which is substituted by Cl-C4-haloalkyl, C1-C4-haloalkoxy or C1-C4-haloalkylmercapto, or is unsubstituted or halogen-substituted phenyl if R1 is fluorine, and R3 is a straight-chain or branched alkyl, alkenyl or alkynyl radical of not more than 6 carbon atoms which is unsubstituted or substituted by halogen, cyano, C2-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyloxy, C2-C4-alkynyloxy or C1-C4-alkylmercapto, or is C3-C7-CyClo~

~.

lZ~47~
- 7 - O.Z. 0050/36410 alkyl, alkyl of not morc than 3 carbon atoms wh;ch ;s sub-stituted by C2-C5-alkoxycarbonyl or C2-C5-alkylmer-captocarbonyl, a 2-t2-alkoxyethoxy)-ethyl, 2-~Z-alkenoxy-ethoxy)-ethyl or 2-(2-alkynoxyethoxy)-ethyl radical of not more than 8 carbon atoms, phenyl ~hich is unsubstituted or subst;tuted by a-kyl, haloalkyl, alkoxy or haloalkoxy, each of not morc than 2 carbon atoms, halogen, n;tro or cyano, or is phcnoxyalkyl of 7 to tO carbon atoms, phenoxy-alkenyl of 8 to 10 carbon atoms, phenoxyalkynyl of 8 to 10 1û carbon atoms or phenylalkyl of 7 to 1û carbon atoms, each of ~h;ch ;s unsubstituted or subst;tuted by alkyl, halo-alkyl, a~koxy or haloalkoxy, each of not more than 2 car-bon atoms, halogen, n;tro or cyano, and Y and Y' are each oxygen.
Hovel N-acylanthranil;c ac;d der;vat;ves are those of the formula C-Y -R~
b~ N~_C_F~2 o ~here R1 ;s halogen, n;tro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-ha~oalkyl~ C1-C4-haloalkoxy or C1-C4-haLoalkylmerCapto, R2 is phenyl which is substitutedmeta or para, or meta and para, by C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-halo-alkylmercapto, C1-C4-haloalkylsulf;nyl, C1-C4-halo-alkylsulfonyl or C1-C4-alkylsulfonyl, R3 is ammonium ~h;ch ;s unsubstituted or subst;tuted by C1-C4-alkyl C~-C4-hydroxyalkyl, C1-C4-haloalkyl or C2-C5-alkoxyalkyl, or is a straight-chain or branched alkyl, alkenyl or alkynyl radical of not more than 1Z carbon atoms ~h;ch is unsubstituted or subst;tuted by halogen, cyano, thiocyano, n;tro, C2-C4-alkylcarbonyl, C1-C4-a~koxy~ C2-C4-a~keny~oxy~ C2-C4-alkynyloxy~ C1-C4-alkylmercapto, C2-C4-alkenylmercapto, C2-C4-alkynyl-1:Z14780 - 8 - ~.Z. 0050/36410 mercapto, C2-C5-alkoxycarbony~, C2-C5-alky~mercapto-carbony~ or C3- or C4-a~keny~carbony~ or ;s a 2-~2-a~kox~ethoxy)-ethyl, 2-(2-a~kenoxyethoxy~-ethyl or 2-~2-alk~noxyethoxy)-ethyl radica~ of not ~ore than 8 carbon S atoms, a 3-~2-alkoxyethoxy)-n-propyl rad~cal of not more than 9 carbon atoms, or phenyl which 15 unsubst;tuted or substituted by halogen, C~-C4-a~ky~, C1-C4-haloalkyl, Cl-C4-a~koxy~ C1-C4-ha~Oa~koxy~ c1_c4_alkylmer-capto, C1-C4-haloalky~mercapto, nitro or cyano, or is phenoxyalkyl of 7 to 12 carbon atoms, phenoxyalkenyl of 8 to 12 carbon atoms, phenoxyalkynyl of 8 to 12 carbon atons or phenyLalkyl of 7 to 12 carbon atoms, each of wh;ch i5 unsubst;tuted or subst;tuted by ha~ogen, C1-C4-a~kyl, C1-C4-haloalk~l, C1-C4-alkoxy~ C1-C4-haloalkoxy, C1-C4-alkylmercapto, C1-C4-haloalkylmercapto, nitro or cyano, and Y and Y' are each oxygen or sulfur, w;th the proviso that R2 may furthermore be unsubstituted or halogen-subst;tuted aryl ~f R1 is fluorine.
The N-acylanthranilic acid der;vatives of the formula I are obta;ned by reacting a a~pound of the formula R~ Y
~ C-Y'-R3 : ~NH2 ~I2), where R1, Y~ Y' and R3 have the above mean;nss, with a compound of the formula . ~ O
" ~ I I I ), ~here R2 has the above mean;ngs and Hal ;s halogen, in the presence or absence of an ;nert organ;c solvent or ;n water and ;n the presence or absence of an ac;d acceptor, at from 0 to 80C (process A). The reaction can be ~4 ~2147~3V
- 9 - O.Z. 0050/36410 carried out under atmospheric or superatmospheric pressure, cont~nuously or batch~ise.
If methyl 6-chloroanthranilate and 3-trifluoro-methy~mercaptobenzoyl fluor;de are used as start~ng ~ate-r;aLs, the course of the react;on can be represented bythe follo~;ng equat;on: C1 2C~3 ~ F-C- ~ NH-C ~

The N-acylanthran;l;c ac;d derivat;ves of the for-mula I are also obta;ned by react~g a o~und of the formula ~1 Y tIV)~

~here R1, Y and R2 have the above mean;ngs, ~ith à compound of the formula R3-Y'-H ~V), ~here R3 and Y' have the above mean;ngs " n the presence or absence of an ;nert organ;c solvent or d;rectly in an excess of the compound of the formula V, ;n the presence or absence of an ;norgan;c or tert;ary organ;c base as a catalyst, at from 0 to 190C (process B). The react;on can be carr;ed out under atmospher;c or superatmospher;c pressure, cont;nuously or batch~ise.
If S-chloro-2-m-tr;fluoromethylmercaptophenyl-4~-3,1-benzoxazin-4-one and n-propyl alcohol are used as start;ng materials, the course of the react;on can be represented by the follo~ing equation:

~6 ~i ~21478~

_ 10 _ o.z. 0050/3641 ~C3H7~ c~e~

Advantageously, solvents or diluents wh;ch are ;nert under the part;cular reaction condit;ons are used for bo~h react;on A and reaction ~. Examples of su;table compounds are halohrdrocarbons, ;n part;cular chloro-hydrocarbons, eg. tetrach~oroethylene, 1,1,2,2- and 1,1,1,2-tetrachloroethane, d;chloropropane, methylene chlor;de, d;chlorobutane, chloroform, chloronaphthalene, dichloro-naphthaleneO carbon tetrachlor;de, 1,1,1- and 1,1,2-tr;-chloroethane, tr;chloroethylene, pentachloroethane, o-, m-and p-d;fluorobenzene, 1,1- and 1,2-d;chloroethane, 1 ,2-c Is-dichloroethylene, chlorobenzene, fluoro-benzene, bromobenzene, iodobenzene, o-, m- and p-dichloro-benzene, o-, p- and m-d~bromobenzene, o-, m- and p-chloro-toluene and 1,2,4-tr;chlorobenzene; ethers, eg. ethyl pro-pyl ether, methyl tert.-butyl ether, n-butyl ethyl ether, di-n-butyl ether, d;isobutyl ether, diisoamyl ether, diiso-propyl ether, anisole, phenetole, cyclohexyl methyl ether, diethyl ether, ethylene glycol dimethyl ether, tetrahydro-furan, dioxane, thloan;sole and ~ dichlorodiethylether; n;trohydrocarbons, eg. n;tromethane, n;troethane, n;trobenzene, o-, m- and p-chloron;trobenzene and o-nitro-toluene; n;tr;les, eg. acetonitr;le, butyron;tr;le, ;so~
butyronitr;le, benzon;tr;le and m-chlorobenzon;tr;le;
al;phat;c and cycloal;phat;c hydrocarbons, eg. heptane, pinane, nonane, o-, m- and p-cymene, gasol;ne ~ract;ons bo;l;ng with;n a range ~rom 70 to 19QC, cyclohexane, methylcyclohexane, decalin, petroleum ether, hexane, naphtha, 2,2,4-tr;methylpentane, 2,2,3-trimethylpentane, 2,3,3-tr;methylpentane and octane; esters, eg. ethyl ace-tate, ethyl acetoacetate and ;sobutyl acetate; am;des, eg.

78~

~ O.Z. 0050/36410 formam;de, methyl formamide and d;methylformamide, ketones, eg. acetone and methyl ethyl ketone, and, ;f appropr;ate, water and mixtures of these so~vents. Advantageously, the solvent is used in an amount of from 100 to 2000, prefe-rably from 200 to 700, X by weight, based on star~ing material II.
Any convent;onal acid acceptor can be used for react;on A. Preferred ac;d acceptors ;nclude tertiary am;nes, alkal;ne earth meta~ compounds, ammon;um compounts and alkali metal compounds, as we~l as mixtures of these.
Zinc compounds may also be used. Examp~es of bas;c com-pounds are potass;um hydroxide, sod;um hydroxide, potas-s;um carbonate, sodium carbonate, lith;um hydroxide, lith-;um carbonate, sod;um bicarbonate, potassium b;carbonate, ca~c;um hydrox;de, ca~c;um ox;de, bar;um oxide, magnes;um hydrox;de, magnes;um ox;de, barium hydrox;de, calc;um car-bonate, magnesium carbonate, magnesium bicarbonate, mag-nes;um acetate, z;nc hydroxide, z;nc oxide, zinc carbon-ate, z;nc blcarbonate, z;nc acetate, sodium formate, so-d;um acetate, trimethylamine, tr;ethylam;ne, tripropyl-am;ne, tri;sopropylam;ne, tr;butylam;ne, tr;;sobutylamine, tr;-sec.-butylam;ne, tr;-tert.-butylam;ne, tribenzylamine, tr;cyclohexylamine, triamylam;ne, trihexylamine, N,N-di-methylaniline, N,N-diethylaniline, N,N-dipropylaniline, N,N-dimethyltolu;d;ne, N,N-diethy~toluidine, N~N-dipropyl-tolu;d;ne, N,N-d;methyl-p-am;nopyridine, N,N-diethyl-p-aminopyr;dine, N,N-d;propyl-p-am;nopyridine, N-methylpyrrolidone, N-ethylpyrrol;done, N-methylp;peridine, N-ethylpiper;dine, N-methylpyrrolidine, N-ethylpyrrol;d;ne, N-methylimidazole, N-ethylimidazole, N-methylpyrrole, N-ethylpyrrole, N-methylmorpholine, N-ethylmorphol;ne, N-methylhexamethylene;mine, N-ethylhexamethylene;mine~
pyridine, quino~ine, a -picoline, ~ -picoline , ~ -picoline, isoquinoline, pyrimidine, acridine, N,N,N',N'-tetramethylethylenediamine, N,N,N',N'-tetraethyl-ethylenediamine, quinoxaline, quinazoline, N-propyl-diisopropylamine, N,N-dimethylcyclohexylamine, 2,6-luti-iZ1~8~

- 12 - O~Z. 005~/3~410 d;ne, 2,4-lut;dine, trifurfurylam;ne and triethylenedi-amine.
Advantageously, the acid acceptor ;s used ;n an amount of from 80 to 120X based on the start;ng mater;al

5 II. Suitable catalysts for react;on B are the above ;n-organic or tert;ary organic bases, but it is also possible to use an alka~; metal or alkaline earth metal hydride, such a lithium hydr;de, sod;um hydride or calcium hydride.
Advantageously, the catalyst ;s used ;n an amount of from 70 to 99.5Z, based on the start;ng materia~ IY.
The starting materials of the formula ~I and III
are used in about stoichiometric amounts, ie. the starting material of the formula III is advantageously used in an amount of from 90 to 110%, based on the starting mater;al of the formula II.
The starting materials of the formulae IV and V
can be used in stoichiometric amounts, but ;~ ;s advan-tageous to employ an excess of not more than 30%, based on starting material of the formula IV, of the starting mater;al of the formula V. However, it ;s also possible to use the start;ng mater;al of the formula V directly as the solvent.
Process A ;s advantageously carried out as fol-lows: the acyl hal;de of the formula III and an equ;va-lent amount of the ac;d acceptor are fed, via two feeds,;nto about an equivalent amount of the anthranilic acid compound of the formula II ;n an inert organic solvent or ;n water, at from 0 to 80C. Stirr;ng ;s then con-tinued for from 5 to 60 m;nutes at room temperature. To isolate the N acylanthran;l;c acid der;vative, the m;~ture is treated w;th water, w;th d;lute acid or, where the radi-cal R3 is covalently bonded, w;th d;lute alkali to sepa-rate off by-products, such as the unreacted anthranilic acid compound, the acyl chlor;de or the hydrochlor;de of the base, and can be dr;ed and then evaporated down. If necessary, the end product may be further purified by recrystallization or chromatography.

~1478~
- 13 - O.Z. OOS0l36410 Process ~ ;s advantageously carr~ed out as fol-~ows: the 4H-3,1-benzoxaz;n-4-one of the formula IV ;s ;ntroduced into a so~ution of not less than an equ;valent amount of the start;ng material of the formula V in an ;n-ert organic solvent, or directly into an excess of thestarting material cf the formula V, in the presence or ab-sence of an ;norgan;c or tert;ary organ;c base as a cata-~yst, at from 0 to 150C. Stirring ;s then cont;nued for from 10 to 240 m;nutes at from Z5 to 190C. How-ever, ;t ;s also poss;ble to ;ntroduce the starting mate-r;al of the formula V ;nto a solut;on of the 4H-3,1-benz-oxaz;n-4-one of the formula IY, 3nd to carry out the re-act;on ;n She manner descr;bed above. To lsolate the N-acy~anthran;l;c acid der;vat;ve, any excess starting mater;al of the formula V can be removed under reduced pressure, and the procedure described under process A
then followed.
The Examples which follow ;llustrate the prepara-tion of same N-acylanthranilic acid derivatives of the formula I.

358 parts of benzoyl chlor;de and 258 parts of tr;ethylam;ne wereintroduced, v;a t~o feeds, into a stir-red ~;xture of 350 parts of 6-fluoroanthranilic acid and 400C parts of methylene chloride at from 25 to 30C in the course of 20 minutes. The reaction m;xture was st;rred for 30 m;nutes at 25C, after wh;ch it was st;rred ;nto 4000 parts of d;lute hydrochlor;c ac;d. The prec;pitate wh;ch separated out was f;ltered off under suct;on, washed w;th water and taken up ;n d;lute sod;um hydrox;de solu-t;on, and the resulting solution was extracted three times ~ith ethyl acetate. The aqueous phasewas then stirred into dilute hydrochloric acid, the precipitate wh;ch separated out was filtered off under suction, ~ashed with water and dried, and 560 parts (96X of theory) of N-ben-zoyl-6-fluoroanthranil;c ac;d of melting point 169-171C
were obta;ned.

.~

~21478~

- 14 O.z. 0050/3~410 15 parts of N-benzoyl-6-fluoroanthranilic ac;d ;n a m;xture of 210 parts of methanol and 10.53 parts of 30X strength sod;um me~hylate were st;rred to g;ve a clear solut;on, wh;ch was then evaporated down under reduced pressure. 16.4 parts (100X of theory) of sod;um N-benzoyl-

6-fluoroanthranilate of melting po;nt 207C (decompo-s;t;on) were obtained.

9 9 of S~fluoro-2-phenyl-3,1-benzoxaz;n-4-one were mixed w;th 35.7 ~ of phenol at 45C ;n the presence of a pellet of sod;um hydrox;de as a catalyst, and stirr;ng was then continued for 3 hours at 185C. The excess phenol ~asd;stilled off under reduced pressure, and the res;due wh;ch rema;ned was first stirred w;th water and f;l-tered off unter suct;on, and then st;rred with a 2:1 mix-ture of petroleum ether and d;ethyl ether and once aga;n f;ltered off under suction. The product was dried to give 10 9 t78X of theory) of phenyl N-benzoy~-6-fluoroanthrani-late of melt;ng po;nt 130-132C.

0.2 part of tr;ethylaminewas added, as a catalyst, to a m;xture of 5 parts of 5-chloro-3-(3'-d;fluoromethoxy-phenyl)-3,1-benzoxazin-4-one and 14 parts of methanol, and the mixture wasstirred for 2 hours at 65C. Itwas then evaporated down under reduced pressure, the res;due was tr;turated w;th water, washed and dr;ed, and 5.3 parts t96X of theory) of methyl N-t3-tr;fluoromethoxybenzoyl)-6-chloroanthran;late of melting point 73-75nC were ob-ta;ned.

12147~
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~ 3 ~ O.Z. 0o~o~36410 The N-acylanthranilic acid derlvatives of the for-mula I may be applied for instance in the form of directly sprayable solutions, powders, suspensions (including high--percentage aqueous, oily or other suspensions), disper-05 sions, emulsions, oil dispersions, pastes, dusts, broad-casting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. m e forms of applica-tion depend entirely on the purpose for which the agents are being used, but they must ensure as fine a distribu-tion of the actlve ingredients according to the inventionas possible.
For the preparation of solutions, emulsions, pastes and oil dlspersions to be sprayed dlrect, mineral oil frac-tions of medlum to high boiling point, such as kerosene or diesel oil, ~urther coal-tar olls, and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydro-carbons such as benzene, toluene, xylene, paraffin, tetra-hydronaphthalene, alkylated naphthalenes and their derivatives such as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclo-hexanone, chlorobenzene, isophorone, etc., and strongly polar solvents such as dimethylformamide, dimethyl sulf-oxide5 N-methylpyrrolidone, water, etc. are suitable.
Aqueous formulations may be prepared from emulsion concentrates, pastes, oil dispersions or wettable powders by adding water. To prepare emulsions, pastes and oil dis-persions the ingredients as such or dissolved in an oil or solvent may be homogenized in water by means of wetting or dispersing agents, adherents or emulsifiers. Concentrates 3~ which are sultable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsify-ing or dispersing agent and possibly solvent or oil.
Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl sulfonates, alkali ~214~7g~

- 31 - O.Z. 0050/36~10 metal and alkallne earth metal salts of dibutylnaphthalene-sulfonic acid, lauryl ether sulfate, fatty alcohol sul-fates, alkali metal and alkaline earth metal salts of fatty acids, salts of sulfated hexadecanols, hepta-05 decanols, and octadecanols, salts of sulfated fatty alco-hol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derlvatives with formaldehyde, condensation products of naphthalene or naphthalenesul-fonlc acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, eth-oxylated octylphenol and ethoxylated nonylphenol, alkyl-phenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotrldecyl alcohol, ~atty alcohol ethylene oxlde condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated poly-oxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, llgnln, sulflte waste liquors and methyl cellulose.
Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.
Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingre-dients to solid carriers. Examples of solid carriers are mlneral earths such as slllcic acld, slllca gels, silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vege-table products such as grain flours, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.
The formulations contain from 0.1 to 95, and prefer-ably 0.5 to 90, % by weight of active ingredient.
Examples of formulations are given below.

l2l~7~a - 32 - O.Z. 0050/36410 I. 90 parts by weight of compound no. 1 is mixed with lO parts by weight of N-methyl-alpha-pyrrolidone. A
mlxture is obtained which is suitable for application in the form of very fine drops.
05 II. 20 parts by weight of compound no. 2 is dissolved in a mixture consisting of 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of olelc acid-N-monoethanol-amide, 2 parts by weight of the calcium salt of dodecyl-benzenesulfonic acid, and 2 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil.
III. 20 parts by weight of compound no. 5 is dlssolved in a mixture consisting o~ 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by welght of the adduct of 7 moles of ethylene oxide and 1 mole of isooctylphenol, and 5 parts by weight of the adduct of 40 moles of ethylene oxlde and 1 r.~ole of castor oil.
IV. 20 parts by weight of compound no. 21 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210 and 280C, and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.
V. 80 parts by weight of compound no. 5 is well mixed with 3 parts by weight of the sodium salt of diiso-butylnaphthalene-alpha-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel, and triturated in a hammer mill.
VI. 5 parts by weight of compound no. 1 is intimately mixed with 95 parts by weight of particulate kaolin. A dust is obtained containing 5% by weight of the active ingredient.

12147~3~

_ 33 - O.Z. 0050/36410 VII. 30 parts by weight of compound no. 21 is intimately mixed with a mixture consisting of 92 parts by weiæht of powdered sllica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of 05 this silica gel. A formulation of the active ingredient is obtained having good adherence.
VIII. 20 parts of compound no. 1 is intimately mixed with 2 parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of a fatty alcohol polyglycol ether, 2 parts of the sodlum salt of a phenolsulfonic acid-urea-form-aldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtalned.
The actlve lngredlents, or agents contalning them, may be applled pre- or postemergence. If certain crop plants tolerate the active ingredients less well when they are applied postemergence, application technlques may be used in which the herblcidal agents are sprayed from sultable equlpment ln such a manner that the leaves of sensitive crop plants are lf possible not touched, and the agents reach the soil or the unwanted plants growlng beneath the crop plants (post-directed, lay-by treatment).
m e amount of active ingredient applled depends on the time of the year, the plants to be combated and their growth stage, the type of soil and the application method -25 employed, and varies from 0.1 to 5 kg/ha and more, but is preferably from 0.25 to 2.0 kg/ha.
The herbicidal action of the N-acylanthranilic acid derivatives of the formula I is demonstrated in greenhouse experiments.
The vessels employed were plastic flowerpots having a volume of 300 cm3, and which were filled with a sandy loam containing about 1.5% humus.
For the postemergence treatment, the plants were first grown in the vessels to a height of from 3 to 15 cm, depending on growth form, before being treated. The rice plants were gro~n ln a peat-enriched substrate. For this ~Z~4~

- 34 - ~.Z. 0050/36410 treatment, elther plants which had been sown directly ln the pots and grown there were selected, or plants which had been grown from seedllngs and were transplanted to the pots a ~ew days before treatment. The application rates 05 were ~rom 0.5 to 3.0 kg of active ingredient per hectare.
The pots were set up in the greenhouse - species from warmer areas at from 20 to 35C, and species from moderate cllmates at 10 to 20C. The experiments were run for 2 to 4 weeks. During this period, the plants were tended and their reactions to the varlous treatments assessed. The scale used for assessment was O to 100, 0 denoting no damage or normal emergence, and 100 denoting nonemergence or complete destruction of at least the vlsible plant parts.
Ihe plants used in the experiments were Arachis hypogaea, Centaurea cyanus, Chenopodium album, Chrysan-themum segetum, Cyperus iria, Desmodium tortuosum, Hordeum vulgare, Mercurialis annua, Nicandra physaloldes, Oryza sativa, Sesbania exaltata, Urtica urens, Zea mays, Cyperus esculentus, Avena fatua, and Galium aparlne.
The experiments show that for instance compounds nos. 1, 5 and 21, applied postemergence at a rate of 0.5 kg/ha, have a selective herbicidal action, parti-cularly on certain unwanted plants from warmer climates.
Compounds nos. 2 and 243, applied postemergence at a rate of 1.0 kg/ha, are also selectively active. For example compounds nos. 3, 46 and 234, applied postemergence at a rate of 3.0 kg/ha, are well tolerated by crop plants and combat unwanted plants in grass crops.
In view of the good tolerance by numerous broadleaved and other crops and the numerous application methods possible, the herbicides according to the invention, or agents containing them, may be used in a ~urther large number of crops for removing unwanted plant growth.
m e following crops may be ment~oned by way of example:

121~7~30 - 35 - O.Z. 0050/36410 Botanical name Common name Allium cepa onions Ananas comosus pineapples 05 Arachis hypogaea peanuts (groundnuts) Asparagus officinal.is asparagus Avena satlva oats 8eta vulgaris spp. altissima sugarbeets Beta vulgaris spp. rapa fodder beets lO Beta vulgaris spp. esculenta table beets, red beets Camellia slnensls tea plants Carthamus tinctorius safflower Carya lllinolnensis pecan trees Cltrus limon lemons 15 Cltrus maxima grapefruits Cltrus retlculata mandarlns Cltrus slnensls orange trees Coffea arablca (Coffea canephora, Coffea liberlca) coffee plants 20 Cucumis melo melons Cucumls satlvus cucumbers Cynodon dactylon Bermudagrass in turf and lawns Elais gulneensls oll palms 25 Fragarla vesca strawberries Glycine max soybeans Gossypium hirsutum (Gossypium arboreum cotton Gossyplum herbaceum 30 GoSSypium vitifolium) Hellanthus annuus sunflowers Hellanthus tuberosus Hevea braslliensls rubber plants Hordeum vulgare barley 35 Humulus lupulus hops Ipomoea batatas sweet potatoes lZ1~78~
- 36 - O.Z. 0050~36410 Juglans regia walnut trees Lens culinaris lentlls Linum usitatissimum flax Lycopersicon lycopersicum tomatoes 05 Malus spp. apple trees Manlhot esculenta cassava Medicago sativa alfal~a (lucerne) Mentha piperita peppermint Musa spp. banana plants 10 Nicothiana tabacum tobacco (N. rustica) Olea europaea olive trees Oryza sativa rice Panlcum mlliaceum 15 Pha~eolus lunatus limabeans Phaseolus mungo mungbeans Phaseolus vulgaris snapbeans, green beansJ
dry beans Pennisetum glaucum 20 Petroselinum crispum parsley spp. tuberosum Picea abies Norway spruce Abies alba ~lr trees Pinus spp. pine trees 25 Pisum sativum English peas Prunus avium cherry trees Prunus domestica plum trees Prunus dulcis almond trees Prunus persica peach trees 30 Pyrus communis pear trees Ribes sylvestre redcurrants Ribes uva-crispa gooseberries Ricinus communis castor-oil plants Saccharum officinarum sugar cane 35 Secale cereale rye Sesamum lndicum sesame ~Z1478~
_ 37 _ O.Z. 0050/36410 Botanical name Common name _ Solanum tuberosum Irlsh potatoes Sorghum bicolor (s. vulgare) sorghum 05 Sorghum dochna Spinacia oleracea spinach Theobroma cacao cacao plants Trifolium pratense red clover Tritlcum aestivum wheat 10 Vaccinium corymbosum blueberries Vacclnium vitis-idaea cranberries Vicla faba tlck beans Vigna sinensis (V. unguiculata) cow peas Vitis vinifera grapes 15 Zea mays Indian corn, sweet corn, maize To lncrease the spectrum of action and to achieve synerglstic effect~ the N-acylanthranilic acid derivatives of the formula I, or agents containing them, may be mixed ; and applied together with numerous representatives of other herbicidal or growth-regulating active ingredient groups. Examples of suitable mixture components are di-azlnes, 4H-3,1-benzoxazine derivatives, benzothiadi-azinones, 2,6-dinitroanilines, N-phenylcarbamates, thiol-carbamates, halocarboxylic acids, trlazines, amldes, other ureas, trlazinones, uraclls, benzofuran derivatives, cyclo-hexane-1,3-dione derivatives, etc.
It may also be useful to apply the novel compounds, or herbicidal agents containing them, either alone or in combination with other herbicides, in admixture with other crop protection agents, e.g., agents for combating pests or phytopathogenic fungi or bacteria. The compounds may also be mixed with solutions of mineral salts used to remedy nutritional or trace element deficiencies. Non--phytotoxic olls and oil concentrates may also be added.

Claims

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. An N-acylanthranilic acid derivative of the formula (I) where R1 is halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl,C1-C4-haloalkoxy or C1-C4-haloalkylmercapto, R2 is unsubstituted or C1-C4-alkyl-substituted thienyl or is phenyl which is m-substituted, p-substituted or m- and p-substituted by C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-haloalkylmercapto, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl or C1-C4-alkylsulfonyl, R3 is a straight-chain or branched alkyl, alkenyl, or alkynyl radical of not more than 12 carbon atoms which is unsubstituted or substi-tuted by halogen, cyano, thiocyano, nitro, C2-C4-alkyl-carbonyl, C1-C4-alkoxy, C2-C4-alkenyloxy, C2-C4-alkynyloxy, C1-C4-alkylmercapto, C2-C4-alkenylmercapto, C2-C4-alkynyl-mercapto, C2-C5-alkoxycarbonyl, C2-C5-alkylmercaptocarbonyl or C3-C4-alkenylcarbonyl, or is C3-C7-cycloalkyl which is unsubstituted or substituted by C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylmercapto, C1-C4-alkylsulfonyl, halogen, trifluoro-methyl, nitro or cyano, a 2-(2-alkoxyethoxy)-ethyl, 2-(2-alkenoxyethoxy)-ethyl or 2-(2-alkynoxyethoxy)-ethyl radical of not more than 8 carbon atoms, a 3-(2-alkoxyethoxy)-n-propyl radical of not more than 9 carbon atoms, phenyl which is unsubstituted or substituted by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylmercapto, C1-C4-haloalkylmercapto, nitro or cyano, or is phenoxyalkyl of 7 to 12 carbon atoms, phenoxyalkenyl of 8 to 12 carbon atoms, phenoxyalkynyl of 8 to 12 carbon atoms or phenylalkyl or 7 to 12 carbon atoms, each of which is unsubstituted or substituted by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylmercapto, C1-C4-haloalkylmercapto, nitro or cyano, and Y and Y' are each oxygen or sulfur, with the proviso that R2 may furthermore be unsubstituted or halogen-substituted phenyl if R1 is fluorine.

2. A N-acylanthranilic acid derivative of the formula I as defined in claim 1, where R1 is halogen, R2 is phenyl which is m- or p-substituted by C1-C4-haloalkyl, C1-C4-haloalkoxy or C1-C4-haloalkylmercapto,R3 is a straight-chain or branched alkyl, alkenyl, or alkynyl radical of not more than 12 carbon atoms which is unsubstituted or substi-tuted by halogen, cyano, thiocyano, nitro, C2-C4-alkyl-carbonyl, C1-C4-alkoxy, C2-C4-alkenyloxy, C2-C4-alkynyloxy, C1-C4-alkylmercapto, C2-C4-alkenylmercapto, C2-C4-alkynyl-mercapto, C2-C5-alkoxycarbonyl, C2-C5-alkylmercaptocarbonyl or C3-C4-alkenylcarbonyl, or is C3-C7-cycloalkyl which is unsubstituted or substituted by C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylmercapto, C1-C4-alkylsulfonyl, halogen, trifluoro-methyl, nitro or cyano, a 2-(2-alkoxyethoxy)-ethyl, 2-(2-alkenoxyethoxy)-ethyl or 2-(2-alkynoxyethoxy)-ethyl radical of not more than 8 carbon atoms, a 3-(2-alkoxyethoxy)-n-propyl radical of not more than 9 carbon atoms, phenyl which is unsubstituted or substituted by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4--alkyl-mercapto, C1-C4-haloalkylmercapto, nitro or cyano, or is phenoxyalkyl of 7 to 12 carbon atoms, phenoxyalkenyl of 8 to 12 carbon atoms, phenoxyalkynyl of 8 to 12 carbon atoms or phenylalkyl or 7 to 12 carbon atoms, each of which is unsubstituted or substituted by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkyl-mercapto, C1-C4-haloalkylmercapto, nitro or cyano, and Y
and Y' are each oxygen, with the proviso that R2 may further-more be unsubstituted or halogen-substituted phenyl if R1 is fluorine.

3. A process for the manufacture of N-acyl-anthranilic acid derivatives of the formula I as defined in claim 1 or 2, wherein either a substituted or unsubstituted anthranilic acid derivative of the formula (II) where R1, Y, Y' and R3 have the meanings given in claim 1, is reacted with approximately stoichiometric amounts of a carboxylic acid halide of the formula (III) where R2 has the meanings given in claim 1 and Hal is halogen, in the presence of an inert organic solvent or in water and in the presence of absence of an acid acceptor, at from 0 to 80°C;
or a substituted or unsubstituted 4H-3,1-benzoxazine derivative of the formula (IV) where R1, Y and R2 have the above meanings, is reacted with a compound of the formula R3-Y'-H (V) where R3 and Y, have the above meanings, in the presence or absence of an inert organic solvent or directly in an excess of the compound of the formula V, in the presence or absence of an inorganic or tertiary organic base as a catalyst, at from 0 to 190°C.

4. A process for the manufacture of N-acly-anthranilic acid derivatives of the formula I as defined in claim 1 or 2, wherein a substituted or unsubstituted anthranilic acid derivative of the formula (II) where R1, Y, Y' and R3 have the meanings given in claim 1, is reacted with approximately stoichiometric amount of a carboxylic acid halide of the formula (III) where R2 has the meanings given in claim 1 and Hal is halogen, in the presence of an inert organic solvent or in water and in the presence of absence of an acid acceptor, at from 0 to 80°C.

5. A process for the manufacture of N-acyl-anthranilic acid derivatives of the formula I as defined in claim 1 or 2, wherein a substituted or unsubstituted 4H-3,1-benzoxazine derivative of the formula (IV) where R1, Y and R2 have the above meanings, is reacted with a compound of the formula R3-Y'-H (V) where R3 and Y, have the above meanings, in the presence or absence of an inert organic solvent or directly in an excess of the compound of the formula V, in the presence or absence of an inorganic or tertiary organic base as a catalyst, at from 0 to 190°C.

6. A process for combatting the growth of unwanted plants, wherein the plants and/or the soil to be kept free from unwanted plant growth are treated with a herbicidally effective amount of an N-acylanthranilic acid derivative of the formula I as defined in claim 1.

7. A process as claimed in claim 6, wherein the amount of N-acylanthranilic acid derivative which is applied is from 0.1 to 5 kg/ha.