Patent ES-8601921-A1 (ES)
Title: 2-Aryl-4,6-dihalogen pyrimidines as antidotes for protecting cultivated plants before phytotoxic damage caused by a herbicide.
IPC: C07D239/34
Filed: 1983-11-14
Abstract: Cpds. of formula (I) are new: (E is (R)n-phenyl, (R)m-thienyl or (R)m-furyl Q1 and Q2 are halogen Y is NR1R2, OR3, SR3, SOR4, SO2R4, N=CR4R5, N=CHNR6R7, SCN or N(R4)CN R is halogen, NO2, CN, XR8, NR9R10, COR11, COOR11, CONR9R10, CSNR9R10, SO2NR9R10, C(OR'11)2R11, SO3H, N=CR4R5, OCON(R11)2 or OCON(R11)OR11, or is a 1-6C alkyl or 3-6C cycloalkyl gp. opt. substd. by halogen, XR8, NR9R10, COR11, COOR11, CONR9R10 or CN, or is a 2-6C alkenyl or alkynyl gp. opt. substd. by halogen or XR8 n = 0-5 and m = 0-4 R1-R3 are H, SO2, 1-6C alkyl, haloalkylsulphonyl, COR4, COOR4, CON(R4)2, CONHR12 etc. R6 and R7 are 1-6C alkyl opt. substd. by halogen X is O, S, SO or SO2 R8 is H, 2-7C alkanoyl etc. R9 and R10 are H, 3-6C alkenyl, alkynyl or cycloalkyl, etc. R11 is H or a 1-6C alkyl, etc. R'11 are as defined for R11 or together form a 1-6C alkylene gp. and R12 is (R)n-phenyl). - (I) are useful as safeners for protecting crop plants from the phytotoxic effects of herbicides, e.g. for pretilachlor and metolachlor on rice. (0/0) EPAB- EP-112280 B A 2-aryl-4,6-dihalopyrimidine of the general formula (I), in which E is a group (II)-(IV), Hal each independently of the other is halogen and Y is a group: -NR1R2, -OR3, -N=CR4R5, -N=CH-NR6R7, -SCN or -N(R4)-CN, in which R is halogen, nitro, cyano, -XR8, -NR9R10, -CO-R11, -COOR11, -CO-NR9R10, a C1-C6alkyl group which is unsubstituted or substituted by halogen or -XR8, or it is a C2-C6alkenyl or C2-C6alkynyl group each unsubstituted or substituted by halogen or -XR8, n is zero or a number from one to three, m and p are a number from zero to two, R1, R2 and R3 independently of one another are each hydrogen, -COR4, -COOR4, -CON(R4)2, -CONHR12, C3-C6alkynyl or C1-C6alkyl or C3-C6alkenyl each unsubstituted or substituted by halogen or C1-C4alkoxy, or R8 is hydrogen, C1-C6alkylcarbonyl, or an unsubstituted C1-C6alkyl group, R9 and R10 independently of one another are each hydrogen, or unsubstituted alkyl, and also one of the two radicals can be -OR11, -COOR11, -CO-N(R11)2 or -CO-N(R11)-OR11, R11 is hydrogen, or a C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl group each unsubstituted or substituted by halogen, R12 is a phenyl radical m (V), with the proviso that when E is an unsubstituted phenyl and Hal is chlorine, one of R1 and R2 in an amino radical Y cannot be hydrogen, -COOR4 or -CONHR12 if the other is hydrogen. - (26pp) USAB- US4648896 A New 2-aryl-4,6- dihalopyrimidines have formula (I) where E is a gp. of formula (II), (III) or (IV) where Y is NR1R2, OR3 (R1, R2 and R3 are H, SO2-alkyl, -SO2-haloalkyl, alkyl, alkenyl or -COR4, R3 may not be H), N=CR4R5 (R4 and R5 are H, alkynyl, or opt. substd. alkyl or alkenyl) or -N=CHR6R7 (R6 and R7 are opt. halo-substd. alkyl R is halogen, NO2, OR8 (R8 is H, alkyl carbonyl, alkenyl-carbonyl, alkynylcarbonyl or opt. substd. alkyl, alkenyl or alkynyl), -NR9R10 (R9 and R10 are H, alkenyl, alkynyl, cycloalkyl or alkyl), -COR11 (R11 is H, alkyl, alkynyl or halogen), -COOR11, -CONR9R10, -OCO-NR11OR, -OCON(R11) -OR11, opt. halo-substd. alkyl or cycloalkyl, or alkenyl or alkynyl m, n and p are 0, 1 or 2. - 5-Amino-4,6- dichloro-2-phenyl pyrimidine is a pref. cpd. (I) are prepd. by reacting an arylamidine of formula E-C(=NH)(NH2) with a malonic acid deriv. of formula A-COCHYCO-A (A is NH2 or 1-6C alkoxy) to yield a 4,6-dihydroxy pyrimidine of formula (V) which is halogenated.