Patent IE-36919-B1 (IE)
Title: Herbicidal allophanimidates
IPC: C07C239/00
Filed: 1972-08-30
Abstract: 1403226 Herbicidal application of Carbamoyl (thio) allophanimidates E I DU PONT DE NEMOURS & CO 15 Sept 1972 [16 Sept 1971 24 May 1972 3 July 1972] 42986/72 Heading A5E [Also in Division C2] The invention comprises herbicidal compounds of the formula wherein: R 1 , R 2 , R 4 and R 5 are each independently selected from hydrogen alkyl of 1 to 8 carbon atoms; alkenyl of 3 or 4 carbon atoms; cycloalkyl of 3 to 8 carbon atoms; cycloalkenyl of 5 to 8 carbon atoms; cycloalkylalkyl of 4 to 10 carbon atoms; bicycloalkyl of 7 to 10 carbon atoms; carbocyclic or heterocyclic arylalkyl of 5 to 9 carbon atoms; alkynyl of 3 to 4 carbon atoms; methoxy; phenyl; the above alkyl and alkenyl groups substituted with 1 to 3 chlorine atoms, bromine, iodine, 1 to 7 fluorine atoms, methoxy, ethoxy, methylthio, ethylthio, cyano, methoxycarbonyl, ethoxycarbonyl, or acetyl; the above cycloalkyl and bicycloalkyl groups substituted with 1 to 3 chlorine atoms, bromine, 1 or 2 methyl groups, or alkyl of 2 to 4 carbon atoms; phenyl substituted with 1 or 2 chlorine atoms, 1 or 2 bromine atoms, fluorine, nitro, cyano, alkyl of I to 4 carbon atoms, methoxy, or trifluoromethyl; and the above arylalkyl groups substituted with a chlorine atom or methyl group; or R 1 and R 2 when taken together and/or R 4 and R 5 when taken together are (CH 2 ) 2 -O-(CH 2 ) 2 - or -(CH 2 ) n - where n is 2 to 6; R 3 is hydrogen; alkyl of 1 to 4 carbon atoms; alkynyl of 3 to 4 carbon atoms; or alkenyl of 3 or 4 carbon atoms; R 6 is alkyl of 1 to 8 carbon atoms; cycloalkyl of 5 to 8 carbon atoms; alkenyl of 3 to 8 carbon atoms; phenyl; or benzyl; and X 1 , X 2 , and X 3 are each independently oxygen or sulfur; provided that: (a) at least one of R 1 , R 2 , R 4 and R 5 is other than hydrogen; (b) no more than one of R 1 , R 3 , R 4 and R 5 is phenyl, substituted phenyl, arylalkyl or substituted arylalkyl; (c) the total number of carbon atoms in R 1 and R 2 does not exceed 10; (d) the total number of carbon atoms in R, and R 5 does not exceed 10; (e) R 1 and R 2 are not both methoxy; (f) R 4 and R 5 are not both methoxy; (g) when one of R 1 , R 2 R, and R 5 , is methoxycarbonylmethyl or ethoxycarbonylmethyl and R 3 is hydrogen then only one of the other R 1 , R 2 , R 4 and R 5 can be other than hydrogen; (h) when R 6 is normal alkyl of 3 to 8 carbon atoms, cycloalkyl of 6 to 8 carbon atoms or benzyl, and R 3 is hydrogen, and one of R 1 , R 2 , R 4 and R 5 is phenyl, then only one of the other R 1 , R 2 , R 4 and R 5 can be other-than hydrogen; and (i) when one of R 1 , R 2 , R 4 and R 5 is 2, 5-dichlorophenyl and R 3 is hydrogen, then only one of the other R 1 , R 2 , R 4 and R 5 can be other than hydrogen; and salts of those compounds in which R 3 is hydrogen. Undesired vegetation is controlled by application of such a compound, e.g. as a composition also containing a surface-active agent and/or a solid or liquid diluent. The compounds of the invention may be combined with all other herbicides and are particularly useful in combination with bromacil (3-sec-butyl-5-bromo-6-methyluracil), diuron (3-/3, 4-dichlorophenyl/-1, 1-dimethylurea), paraquat (1, 1'-dimethyl-4, 4'-bipyridinium ion), 1, 1-dimethyl-3, 3-(N-tert-butylcarbamoyloxyphenyl)urea, 4-amino-6-tert-butyl-3-methyl-thioas-triazin-5(4H)-one, and the S-triazines such as 2-chloro-4-ethylamino-6-isopropylamino-S- triazine. The compounds can be formulated for herbicidal use in the various ways which are conventional for herbicides of similar physical properties. Useful formulations include wettable powders, oil suspensions and solutions, aqueous dispersions, dusts, granules, pellets, high strength compositions, and ultra-lowvolume or low-volume compositions, e.g. in suspensions in carriers such as petroleum oils, dialkylformamides, N-alkylpyrridones and dimethylsulphoxide.
[GB1403226A]