Reference

N-Phenylsulfonyl-N'-pyrimidinyl- and -triazinylureas

N-Phenylsulfonyl-N'-pyrimidinyl- and -triazinylureas. Schurter, Rolf; Foery, Werner; Meyer, Willy (Ciba-Geigy A.-G. , Switz.). 53730-99-7 and 89392-03-0 are also occured in this study. Eur. Pat. Appl. EP 96002 A2 7 Dec 1983, 51 pp. DESIGNATED STATES: R: AT, BE, CH, DE, FR, GB, IT, LI, NL. (German). (European Patent Organization). CODEN: EPXXDW. CLASS: IC: C07D239-52; C07D239-42; C07D239-46; C07D251-16; A01N047-36. ICA: C07C143-78. APPLICATION: EP 83-810212 20 May 1983. PRIORITY: CH 82-3232 26 May 1982. DOCUMENT TYPE: Patent CA Section: 28 (Heterocyclic Compounds (More Than One Hetero Atom)) Section cross-reference(s): 5 The title ureas I [R = H, C1-9 (un)substituted alkyl (un)substituted with (un)substituted Ph, (un)substituted C3-9 cycloalkyl, Ph, or 5-6 membered heterocycle; m = 1, 2; R1 = H, halo, C1-5 alkyl, C2-5 alkenyl, Z1R5; R2 = R1, C1-4 haloalkyl, NO2, carboxylate ester, (un)substituted CONH2; R3, R4 = H, C1-4 alkyl, alkoxy, alkylthio, haloalkyl, -alkoxy, or -alkylthio, halo, C2-5 alkoxyalkyl, (un)substituted-amino or -aminoethoxy, R5 = C1-6 aliph. group, C1-5 haloalkyl or -alkenyl, C2-6 alkoxyalkyl; X = CH, N; Z = O, S; Z1 = O, S, S(O), SO2], and their salts, useful as plant growth regulators (no data), and herbicides, were prepd. by 3 methods. Propyne (g) reacted with 2-IC6H4SO2NH2 in DMF previously treated with NEt3, PdCl2(PPh3)2, and CuI to give 80% 2-MeCYCC6H4SO2NH2 which reacted with 4,6-dimethoxy-2-phenoxycarbonylaminopyrimidine in dioxane contg. 1,8-diazabicyclo[5.4.0]undec-7-ene to give 74% urea II. At 70.8 ppm, II gave complete preemergence control of Nasturtium officinalis, Agrostis tenuis, Stellaria media, and Digitaria sanguinalis. .

N-benzenesulfonyl-N'-pyrimidin-2-ylurea derivative

N-benzenesulfonyl-N'-pyrimidin-2-ylurea derivative. (du Pont de Nemours, E. I., and Co., USA). Jpn. Kokai Tokkyo Koho JP 61263961 A2 21 Nov 1986 Showa, 15 pp. (Japan) CODEN: JKXXAF. CLASS: ICM: C07D239-54. ICS: A01N047-36. APPLICATION: JP 86-80276 9 Apr 1986. PRIORITY: US 85-720702 10 Apr 1985; US 86-826682 10 Feb 1986. DOCUMENT TYPE: Patent CA Section: 28 (Heterocyclic Compounds (More Than One Hetero Atom)) Section cross-reference(s): 5 The title compd. (I), useful as a herbicide, was prepd. Thus, reaction of dioxobenzisothiazolone deriv. II (R = Cl) with NaOMe in MeOH/DMF at 85° for 12 h and treatment of the resulting II (R = OMe) with MeCH2CH2SH in DMF contg. KOCMe3 at 110° for 3 h gave, after acidification, II (R = OH). Alkylation of this with CHClF2 in CH2Cl2 and aq. KOH soln. contg. 89392-03-0 and 62473-95-4 are also in the experiment. Bu4N+ Br- at b. temp. for 6 h followed by alcoholysis with EtOH contg. dry HCl gave Et 2-(aminosulfonyl)-4-(difluoromethoxy)benzoate, whose condensation with Ph (4,6-dimethoxy-2-pyrimidinyl)carbamate in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene at 25° for 1 h gave I. I was effective against common weeds, e.g. Echinochloa crusgalli. .