Patent ES-8602643-A1 (ES)
Title: N-sulfonyl-imino-thiocarbonic-acid diesters as herbicide antagonists for the protection of rice cultures.
IPC: A01N25/32
Filed: 1983-12-02
Abstract: Compsns. for protecting rice crops from damage by herbicides comprise cpds. of formula (I). In (I), n=0-3; R is halogen, CN, NO2, YR1, COOR3, NR3R4, CONR3R4, NHCONR3R4 or SO2NR3R4, or two adjacent R gps. may form a 3- or 4-membered satd. or unsatd. hydrocarbon chain in which one C atom may be replaced by O or S and/or 1-3C atoms may be replaced by N. R1 is 1-4C alkyl, 3-6C alkenyl, 3-6C alkynyl, phenyl or aralkyl opt. substd. by halogen, CN, NO2, 1-4C alkoxy, 2-5C alkoxycarbonyl, CONH2, SO2NH2, 1-4C mono- or dialkylcarbamoyl or 1-4C mono- or dialkylsulphamoyl; R1 and R2 are H or 1-4C alkyl, 3-6C alkenyl, 3-6C alkynyl, phenyl or aralkyl opt. substd. by halogen, CN, NO2, 1-4C alkyl, 1-4C haloalkyl or 1-4C alkoxy, or R1 and R2 may form a 5- or 6-membered satd. or unsatd. C-bonded heterocyclic gp. which contains 1-3 heteroatoms, is opt. benzene-fused and is opt. substd. by halogen and/or Me; R3 is a 1-4C alkyl, 3-6C alkenyl, 3-6C alkynyl or 3-6C cycloalkyl gp. opt. substd. by halogen, CN, NO2 or 1-4C alkyl, and R4 is H, R3 or phenyl or aralkyl opt. substd. by halogen, CN, NO2, 1-4C alkyl, 1-4C haloalkyl or 1-4C alkoxy, or NR3R4 is a 5- or 6-membered satd. or unsatd. ring opt. contg. another O, S, N or NMe ring member; X is O or S; Y is a bond, O, S, SO, SO2, NH or NMe. - (I) are esp. useful as safeners for chloroacetanilide herbicides, e.g. metolachlor or pretilachlor, as well as thiocarbamage herbicides such as thiobencarb and ordram. EPAB- EP-112289 B A herbicidal composition for controlling weeds in rice crops which contains, in addition to a chloroacetanilide herbicide or another herbicide, a safener for protecting said rice crops from the phytotoxic action of the herbicide, which composition contains as safener an N-sulfonylimino-dithiocarbonate of formula I wherein n is0, 1 or 3. - R is halogen, cyano, nitro, a -Y-C1-C4 alkyl radical, -Y-C3-C6 alkenyl, -Y-C3-C6 alkynyl, -Y-phenyl or -Y-aralkyl, each unsubstituted or substituted by halogen, cyano, nitro, C1-C4 alkoxy, C1-C4-alkoxy-carbonyl, carbamoyl, sulfamoyl, C1-C4 mono- or dialkylcarbamoyl, C1-C4 mono- or dialkylsulfamoyl, or is a -COOR3, -NR3R4, -NHCONR3R or -SO2NR3R4 radical, or two adjacent R substituents together form a 3- or 4-membered, saturated or unsaturated hydrocarbon chain, the chain members of which can be replaced once by oxygen or sulfur and/or once to three times by nitrogen, R1 and R2 are each independently at the other a C1-C4 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, phenyl or aralkyl group which is unsubstituted or substituted by halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 alkoxy, or one of R1 and R2 may also be hydrogen or can form a 5- or 6-membered, saturated or unsaturated heterocycle which is bound through a carbon atom, contains 1-3 hetero atoms can can also be fused with benzene nuclei, and which may be substituted by halogen and/or methyl. - R3 is a C1-C4 alkyl, C3-C6 alkenyl, C3-C6 alkynyl or C3-C6 cycloalkyl group, each of which may be substituted by halogen, cyano, nitro or C1-C4 alkyl, R4 is hydrogen, has the same meaning as R3 or is a phenyl or aralkyl group which may be substituted by halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 alkoxy or R3 and R4 together with the nitrogen atom to which they are attached form a 5- or 6-membered, saturated or unsaturated heterocycle which may also contain oxygen, sulfur, nitrogen or a methylimino group as ring member, X is oxygen or sulfur, and Y is a direct bond - EP-112289 B Compsns. for protecting rice crops from damage by herbicides comprise cpds. of formula (I). In (I), n=0-3; R is halogen, CN, NO2, YR1, COOR3, NR3R4, CONR3R4, NHCONR3R4 or SO2NR3R4, or two adjacent R gps. may form a 3- or 4-membered satd. or unsatd. hydrocarbon chain in which one C atom may be replaced by O or S and/or 1-3C atoms may be replaced by N. R1 is 1-4C alkyl, 3-6C alkenyl, 3-6C alkynyl, phenyl or aralkyl opt. substd. by halogen, CN, NO2, 1-4C alkoxy, 2-5C alkoxycarbonyl, CONH2, SO2NH2, 1-4C mono- or dialkylcarbamoyl or 1-4C mono- or dialkylsulphamoyl; R1 and R2 are H or 1-4C alkyl, 3-6C alkenyl, 3-6C alkynyl, phenyl or aralkyl opt. substd. by halogen, CN, NO2, 1-4C alkyl, 1-4C haloalkyl or 1-4C alkoxy, or R1 and R2 may form a 5- or 6-membered satd. or unsatd. C-bonded heterocyclic gp. which contains 1-3 heteroatoms, is opt. benzene-fused and is opt. substd. by halogen and/or Me; R3 is a 1-4C alkyl, 3-6C alkenyl, 3-6C alkynyl or 3-6C cycloalkyl gp. opt. substd. by halogen, CN, NO2 or 1-4C alkyl, and R4 is H, R3 or phenyl or aralkyl opt. substd. by halogen, CN, NO2, 1-4C alkyl, 1-4C haloalkyl or 1-4C alkoxy, or NR3R4 is a 5- or 6-membered satd. or unsatd. ring opt. contg. another O, S, N or NMe ring member; X is O or S; Y is a bond, O, S, SO, SO2, NH or NMe. - (I) are esp. useful as safeners for chloroacetanilide herbicides, e.g. metolachlor or pretilachlor, as well as thiocarbamage herbicides such as thiobencarb and ordram. (Dwg.0/0) USAB- US4740236 A Compsn. for redn. of phytotoxic action of haloacetamide and thiocarbamate herbicides on rice crops comprises an inert carrier and an antidote which is an N-sulphonyliminithiocarbonic acid diester of formula (I) where n is 0-3; R is halogen, CN, (halo)-alkyl, (halo)alkoxy, alkylthio, alkylsulphonyl, sulphamoyl, dialkylsulphamoyl or is -COOR3 (in which R3 is alkyl, alkenyl, alkynyl or cycloalkenyl, each being opt. substd.); R1 and R2 are each (halo)alkyl, alkoxyalkyl, carbalkoxymethyl, carbamoylmethyl (halo)alkenyl, alkynyl, Ph, (halo)benzyl; X is O or S. - N-(4-Chlorobenzene sulphonyl)-imino- dithiocarbonic acid dimethyl ester is typical. - Cpds. (I) are prepd. by reaction of a benzenesulphonamide of formula (II) with CS2 and then reaction of the prod. with a halide or sulphate e.g. of formula R1-Hal and/or an alcohol R2OH.  (12pp)