Patent DE-4213715-A1 (DE)
Title: New cyclohexene-di:carboxylic acid di:amide derivs. - used as selective herbicides, plant growth regulators, desiccants and defoliants
Inventor: KLINTZ RALF DR
IPC: C07D307/12
Filed: 1992-04-25
Abstract: N-(Substd. phenyl)-cyclohexene -1,2-dicarboxylic acid diamide derivs. of formula (I) and their salts are new. In (I), R1, R2 = (i) H; (ii) alkyl, alkenyl or alkynyl all opt. substd. (iii) 3-8C cycloalkyl; or (iv) phenyl or heterocyclyl (contg. 1-4 heteroatoms selected from 1-4N, 1 or 2 O and 1 or 2 S), both opt. C-substd. by one or more of OH, halogen, CN, NO2, CF3, halogen and alkyl; if R1 = H or alkyl, then additionally: R2 = (v) OH, alkoxy, alkenyloxy, alkynyloxy, 3-7C cycloalkoxy, 5-7C cycloalkenyloxy, haloalkoxy, haloalkenyloxy, (3-7C) cycloalkyl-alkoxy, alkoxycarbonyl, cyanoalkoxy, hydroxyalkoxy, alkoxyalkoxy, alkoxycarbonylalkoxy, alkylthioalkoxy or mono- or dialkylamino-alkoxy; (vi) phenylalkoxy, phenylalkenyloxy or phenylalkynyloxy (in which 1 or 2 CH2 gps. of the aliphatic chain are opt. replaced by O, S and/or N (alkyl) and phenyl rings are opt. substd. by 1-3 of alkyl, 2-6C alkenyl, halogen, CN, NO2, haloalkyl alkoxy and alkoxycarbonyl), or (vii) NR7R8; or NR1R2 = non-aromatic heterocycle which can contain 1-3 N and/or one O or S and 1 or 2 CO gps. and is opt. mono-, di- or tri-alkyl substd.; R7, R8 = H, alkyl, alkenyl, alkynyl, 3-6C cycloalkyl, haloalkyl, alkylcarbonyl, alkoxycarbonyl, alkoxyalkyl or phenyl, opt. substd.; or NR7R8 = 4-7 membered heterocycle opt. contg. a further N, 0 or S heteroatom; R3 = H or alkyl; R4 = H or halogen; R5 = H, halogen, NO2, CN or CF3; R6 = e.g. heterocyclyl (contg. 1-4 heteroatoms selected from 1-4N, 1-2 O and 1-2 S, opt. with 1 or 2 CH2 gps. replaced by CO), opt. C-substd. etc. or R5 + R6 = satd. or partially or completely unsatd. 3-5 membered hydrocarbon chain (opt. contg. 1 or 2 O, S or N and/or one CO or alkoxyimino as chain member; and opt. substd. by 1 or 2 of CN, NO2, NH2, halogen, alkyl, haloalkyl, 2-6C alkenyl, 2-6C alkynyl, cyanoalkyl, alkoxycarbonylalkyl, phenylalkyl and heterocyclyl-alkyl (where heterocyclyl contains 1-4 heteroatoms selected from 1-4N, 1-2 O and 1-2 S)); unless otherwise specified, all alkyl moieties contain 1-6C, and alkenyl and alkynyl moieties 3-6C; and heterocycles are satd. or partially or completely unsatd. and have 3-8 members. Also claimed are certain new 3,4,5,6-tetrahydrophthalimide, 3,4,5,6-tetrahydro-phthalisoimide and tetrahydrophthalamic acid deriv. intermediates. USE/ADVANTAGE - (I) are herbicides (claimed), plant growth regulators, defoliants (claimed) and desiccants (claimed); the new intermediates have the same activities. As herbicides, the cpds. are esp. useful for combatting dicotyledonous weeds and are useful as selective herbicides in wheat, rice, maize, soya and cotton. (I) have good herbicidal activity and higher selectivity (better culture plant compatibility) than related known cpds. The cpds. are useful as desiccants/defoliant for defoliation of cotton or desiccating the ground parts of potatoes, sunflowers, soybeans and rape to facilitate mechanical harvesting. They also promote abscission of citrus fruits, olives and other fruits. The cpds. are applied pre- or post-emergence at 0.001-3 (pref. 0.01-1) kg/ha, or to seeds.