Arylphenyl ethers having herbicidal activity

Claim 2

A diphenyl ether of the general formula wherein Ar is a phenyl or pyridyl group, which groups are substituted with 1,2 or 3 substituents, selected from the group consisting of a halogen atom, a cyano group, a nitro group, an optionally halogenated alkyl, alkoxy and alkylthio group having 1-6 carbon atoms, an alkylsulphonyl group having 1-4 carbon atoms, and an alkanoyl group having 1-4 carbon atoms; n is 1 or 2; R 1 and R 2 are equal or different and represent hydrogen atoms or alkyl groups having 1-4 carbon atoms; R 3 is a hydrogen atom, an alkyl or alkenyl group having 1-4 carbon atoms and optionally substituted with an alkoxycarbonyl group with 2-5 carbon atoms; or R 2 and R 3 together form an alkylene group with 2-5 carbon atoms; and R 4 and R 5 are equal or different and represent alkyl groups having 1-6 carbon atoms; or R 4 and R 5 together form an alkylene group having 2 or 3 carbon atoms.

Claim 3

A compound as claimed in Claim 1, of the general formula wherein Ar' is a phenyl group, substituted in the 2,4- or 2,4,6--positions with substituents selected from the group consisting of a halogen atom, a nitro group and a trifluoromethyl group, with the proviso that one of the substituents at most represents a nitro group or a trifluoromethyl group, R 3 ' is an alkyl or alkenyl group having 1 or 2 carbon atoms, and R 4 and R 5 have the meanings given in Claim 1.

Claim 4

A compound as claimed in Claim 2, selected from the group consisting of dimethyl and diethyl esters of 1-[N-{2-nitro-5-(2,4-dichlorophenoxy)phenyl}amino]ethane phosphonic acid and of 1-[N-{2-nitro-5-(2-chloro-4-trifluoromethyl- phenoxy)phenyl}amino]ethane phosphonic acid.

Claim 5

A method of preparing new diphenyl ethers, characterized in that compounds of the general formula wherein Ar, n, R 1 , R 21 R 3 , R 4 and R 5 have the meanings given in Claim 1, are prepared in a manner known per se for the preparation of related compounds.

Claim 6

A method as claimed in Claim 4, characterized in that compounds of the general formula wherein Ar, R 1 , R 2 , R 3 , R 4 and R 5 have the meanings given in Claim 1, are prepared by reacting a compound of the general formula wherein Ar and R 1 have the meanings given in Claim 1, with an aliphatic aldehyde or ketone of the general formula R3 is a hydrogen atom, an alkyl or alkenyl group having 1-4 carbon atoms and optionally sutstituted with an alkoxycarbonyl group with 2-5 carbon atoms; or R 2 and R 3 together form an alkylene group with 2-5 carbon atoms; and R 4 and R 5 are equal or different and represent alkyl groups having 1-6 carbon atoms; or R4 and R 5 together form an alkylene group having 2 or 3 carbon atoms.

Claim 7

Particularly suitable have proved new compounds of the general formula wherein Ar' is a phenyl group, substituted in the 2,4- or 2,4,6--positions with substituents selected from the group consisting of a halogen atom, a nitro group and a trifluoromethyl group, with the proviso that one of the substituents at most represents a nitro group or a trifluoromethyl group, R 3 ' is an alkyl or alkenyl group having 1 or 2 carbon atoms, and R 4 and R 5 have the above meanings.

Claim 8

Particularly suitable have proved new compounds of the general formula wherein Ar' is a phenyl group, substituted in the 2,4- or 2,4,6--positions with substituents selected from the group consisting of a halogen atom, a nitro group and a trifluoromethyl group, with the proviso that one of the substituents at most represents a nitro group or a trifluoromethyl group, R 3 ' is an alkyl or alkenyl group having 1 or 2 carbon atoms, and R 4 and R 5 have the above meanings.

Claim 9

Dimethyl and diethyl esters of 1-[N-{2-nitro-5-(2,4-dichlorophenoxy)phenyl}amino]ethane phosphonic acid and of 1-[N-{2-nitro-5-(2-chloro-4-triflueromethylphenoxy)phenyl}amino] ethane phosphonic acid have proved to be excellently suitable for use as active substances in compositions having selective herbicidal activity, such as dimethyl 1-[N-{2-nitro-5-(2,4-di- chlorophenoxy)phenyl}amino]esthane phosphcnate (1), diethyl 1-[N-{2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl}amino]-ethane phosphonate (2), dimethyl 1-[N-{2-nitro-6-(2-chloro-4-trifluoromethylphenoxy)phenyl}amino]ethane phosphenit '3), and

Claim 10

Dimethyl and diethyl esters of 1-[N-{2-nitro-5-(2,4-dichlorophenoxy)phenyl}amino]ethane phosphonic acid and of 1-[N-{2-nitro-5-(2-chloro-4-triflueromethylphenoxy)phenyl}amino] ethane phosphonic acid have proved to be excellently suitable for use as active substances in compositions having selective herbicidal activity, such as dimethyl 1-[N-{2-nitro-5-(2,4-di- chlorophenoxy)phenyl}amino]esthane phosphcnate (1), diethyl 1-[N-{2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl}amino]-ethane phosphonate (2), dimethyl 1-[N-{2-nitro-6-(2-chloro-4-trifluoromethylphenoxy)phenyl}amino]ethane phosphenit '3), and

Claim 11

Other examples cf new diphenyl ethers according to the invention which may be used as selective herbicides, are: (5) diethyl 1-[N-{2-nitro-5-(2,4,6-trichlorophenoxy)phenyl}amino, ethane phosphonate; (6) dibutyl 1-[N-{2-nitro-5-(2,4,6-trichlorophenoxy)phenyl}amino]-ethane phosphonate; (7) dimethyl 1-[N-{2-nitro-5-(4-methylphenoxy)phenyl}amino]ethane phosphonate; (8) dimethyl 1-[N-(2-nitro-5-(4-trifluoromethylphenoxy)phenyl}- amino]ethane phosphonate; (9) dimethyl 1-[N-{2-nitro-5-(4-cyanophenoxy)phenyl}amino]ethane phosphonate; (10) dimethyl 1-[N-{2-nitro-5-(4-n-propylphenoxy)phenyl}amino]-ethane phosphonate; (11) dimethyl 1-[N-{2-nitro-5-(4-tert.-butylphenoxy)phenyl}amino]-ethane phosphonate; (12) dimethyl 1-[N-{2-nitro-5-(2-methyl-4-chlorophenoxy)phenyl}- amino]ethane phosphonate; (13) diethyl 2-[N-{2-nitro-5-(2-chloro-4-trifluoromethylpheoxy)-phenyl}amino]ethane phosphonate; (14) dimethyl 1-[N-{2-nitro-5-(2,6-dichloro-4-trifluoromethylphe- noxy)phenyl}amino]ethane phosphonate; ( 15 ) dimethyl 1-[N-{2-nitro-5-(4-bromophenoxy)phenyl}amino]ethane phosphonate; (16) dimethyl 1-[N-{2-nitro-5-(2,4-dibromophenoxy)phenyl}amino]-ethane phosphonate; ( 17 ) diethyl 1-[N-{2-nitro-5-(2,4-dibromophenoxy)phenyl}amino]-ethane phosphonate; (18) dimethyl 1-[N-{2-nitro-5-(4-chlorophenoxy)phenyl}amino]-ethane phosphonate; (19) diethyl 1-methyl-1-[N-{2-nitro-5-(2,4-dichlorophenoxy)phenyl}- amino]ethane phosphonate; (20) diethyl 1-[N-{2-nitro-5-(2,4-dichlorophenoxy)phenyl}amino]- butene-2 phosphonate; (21) diethyl N-[2-nitro-5-(2,4-dichlorophenoxy)phenyl]aminomethane phosphonate; (22) dimethyl 1-methyl-1-[N-{2-nitro-5-(2,4-dichlorophenoxy)phenyl}- amino propane phosphonate; (23) dimethyl 1-ethoxycarbonylmethyl-1-[N-{2-nitro-5-(2,4-dichloro- phenoxy)phenyl}amino]ethane phostrhonate; a compound of the general formula wherein the symbols have the meanings given in Claim 1.

Claim 12

A composition as claimed in Claim 8 or 9, characterized in that the composition comprises as an active substance a compound of the general formula wherein Ar' and R 3 ' have the meanings given in Claim 2, and R 4 and R 5 have the meanings given in Claim 1.

Claim 13

A composition as claimed in Claims 8 or 9, characterized in that the composition comprises as an active substance a compound selected from the group consisting of dimethyl and diethyl esters of 1-[N-{2-nitro-5-(2,4-dichloro- phenoxy)phenyltaminojethane phosphonic acid and of 1-[N-{2--nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl}amino]ethane phosphonic acid.

Claim 14

A method of preparing a herbicidal composition or a composition for leaf-desiccation as claimed in any of claims 8-11, characterized in that, in addition to a solid or liquid inert carrier material, a compound of the general formula wherein the symbols have the meanings given in Claim 1, is incorporated in the composition, if desired while adding other herbicidal and/or pesticidal compounds, artificial manures and/or auxiliary substances such as surface-active substances and stabilizers.