Process for the preparation of triazolinone herbicides

A process for the preparation of compounds of type (I), ##STR36## wherein X=O or S,

• R.sup.1 =(C.sub.2 -C.sub.8) alkoxyalkyl, (C.sub.2 -C.sub.8) haloalkoxyalkyl, (C.sub.1 -C.sub.8) alkyl, (C.sub.1 -C.sub.8) haloalkyl, (C.sub.1 -C.sub.8) cyanoalkyl, (C.sub.2 -C.sub.8) alkylthioalkyl, (C.sub.2 -C.sub.8) alkylsulfinylalkyl, (C.sub.2 -C.sub.8) alkylsulfonylalkyl, (C.sub.7 -C.sub.8) arylalkyl, (C.sub.2 -C.sub.8) alkenyl, (C.sub.2 -C.sub.8) haloalkenyl, (C.sub.2 -C.sub.8) alkinyl, (C.sub.2 -C.sub.8) haloalkinyl, aryl, that may be substituted one or more times with halogen, (C.sub.1 -C.sub.3) alkyl or (C.sub.1 -C.sub.3) alkoxy, heteroaryl, where heteroaryl may optionally be substituted by halogen,
• R.sup.2 and R.sup.3, independently of one another represent, H, (C.sub.2 -C.sub.6) alkoxyalkyl, (C.sub.2 -C.sub.6) haloalkoxyalkyl, (C.sub.1 -C.sub.6) alkyl, (C.sub.1 -C.sub.6) haloalkyl, (C.sub.1 -C.sub.6) cyanoalkyl, (C.sub.1 -C.sub.6) alkylthio, (C.sub.2 -C.sub.6) alkylthioalkyl, (C.sub.2 -C.sub.6) alkylsulfinylalkyl, (C.sub.2 -C.sub.6) alkylsulfonylalkyl, (C.sub.7 -C.sub.8) arylalkyl, (C.sub.2 -C.sub.6) alkenyl, (C.sub.2 -C.sub.6) haloalkenyl, (C.sub.2 -C.sub.6) alkinyl, (C.sub.2 -C.sub.6) haloalkinyl, aryl, that may be substituted one or more times with halogen, (C.sub.1 -C.sub.3) alkyl or (C.sub.1 -C.sub.3) alkoxy, heteroaryl, where
• R.sup.1 and R.sup.2 may also be associated to form a ring to produce structure (II), ##STR37## wherein n and m independently of one another are 0, 1, 2 or 3,
• Z=CR.sup.4 R.sup.5, O, S, S(O), S(O).sub.2, N((C.sub.1 -C.sub.4)alkyl), N((C.sub.1 -C.sub.4)haloalkyl), C.dbd.O, C.dbd.N--R.sup.4 or C.dbd.S,
• R.sup.4 =H, (C.sub.1 -C.sub.3) alkyl, halogen, (C.sub.1 -C.sub.6) alkoxy, (C.sub.1 -C.sub.6) haloalkyl, (C.sub.1 -C.sub.6) haloalkoxy, (C.sub.2 -C.sub.6) alkylcarbonyloxy or (C.sub.2 -C.sub.6) haloalkylcarbonyloxy,
• R.sup.5 =H, (C.sub.1 -C.sub.3) alkyl or halogen, where R.sup.4 and R.sup.5, independently of one another, can substitute the ring one or more times and occupy up to 12 (m=3, n=3) positions,
• Q stands for one of the radicals ##STR38## wherein W=O or S,
• R.sup.6 =H, halogen,
• R.sup.7 =H, (C.sub.1 -C.sub.8) alkyl, (C.sub.1 -C.sub.8) haloalkyl, halogen, OH, OR.sup.12, SH, S(O).sub.p R.sup.12, COR.sup.12, CO.sub.2 R.sup.12, C(O)SR.sup.12, C(O)NR.sup.14 R.sup.15, CHO, CR.sup.14 .dbd.NOR.sup.21, CHCR.sup.22 CO.sub.2 R.sup.12, CH.sub.2 CHR.sup.22 CO.sub.2 R.sup.12, CO.sub.2 N.dbd.CR.sup.16 R.sup.17, NO.sub.2, CN, NHSO.sub.2 R.sup.18, NHSO.sub.2 NHR.sup.18, NR.sup.12 R.sup.23, NH.sub.2 or phenyl, optionally substituted by R.sup.24,
• p=0,1 or 2,
• R.sup.8 =(C.sub.1 -C.sub.2) alkyl, (C.sub.1 -C.sub.2) haloalkyl, OCH.sub.3, SCH.sub.3, OCHF.sub.2, halogen, CN or NO.sub.2,
• R.sup.9 =H, (C.sub.1 -C.sub.3) alkyl or halogen,
• R.sup.10 =H, (C.sub.1 -C.sub.3) alkyl, halogen, (C.sub.1 -C.sub.3) haloalkyl, cyclopropyl, Vinyl, (C.sub.2 -C.sub.8) alkinyl, CN, C(O)R.sup.23,CO.sub.2 R.sup.23, C(O)NR.sup.23 R.sup.25, CR.sup.19 R.sup.20 CN, CR.sup.19 R.sup.20 C(O)R.sup.23, CR.sup.19 R.sup.20 CO.sub.2 R.sup.23, CR.sup.19 R.sup.20 C(O)NR.sup.23 R.sup.25, CHR.sup.19 OH, CHR.sup.19 OC(O)R.sup.23 or OCHR.sup.19 OC(O)NR.sup.23 R.sup.25, or, when Q equals Q-2, R.sup.9 and R.sup.10 can together with the carbon atom to which they are bound be C.dbd.O,
• R.sup.11 =H, (C.sub.1 -C.sub.6) alkyl, (C.sub.1 -C.sub.6) haloalkyl, (C.sub.3 -C.sub.6) haloalkenyl, (C.sub.2 -C.sub.6) alkoxyalkyl, (C.sub.3 -C.sub.6) alkenyl, (C.sub.3 -C.sub.6) alkinyl, (C.sub.3 -C.sub.6) haloalkinyl, (C.sub.4 -C.sub.7) cycloalkylalkyl, ##STR39## R.sup.12 =(C.sub.1 -C.sub.8) alkyl, (C.sub.3 -C.sub.8) cycloalkyl, (C.sub.3 -C.sub.8) alkenyl, (C.sub.3 -C.sub.8) alkinyl, (C.sub.1 -C.sub.8) haloalkyl, (C.sub.2 -C.sub.8) alkoxyalkyl, (C.sub.2 -C.sub.8) alkylthioalkyl, (C.sub.2 -C.sub.8) alkylsulfinylalkyl, (C.sub.2 -C.sub.8) alkylsulfonylalkyl, (C.sub.4 -C.sub.8) alkoxyalkoxyalkyl, (C.sub.4 -C.sub.8) cycloalkylalkyl, (C.sub.6 -C.sub.8) cycloalkoxyalkyl, (C.sub.4 -C.sub.8) alkenyloxyalkyl, (C.sub.4 -C.sub.8) alkinyloxyalkyl, (C.sub.3 -C.sub.8) haloalkoxyalkyl, (C.sub.4 -C.sub.8) haloalkenyloxyalkyl, (C.sub.4 -C.sub.8) haloalkinyloxyalkyl, (C.sub.6 -C.sub.8) cycloalkylthioalkyl, (C.sub.4 -C.sub.8) alkenylthioalkyl, (C.sub.4 -C.sub.8) alkinylthioalkyl, (C.sub.1 -C.sub.4) alkyl, substituted by phenoxy or benzyloxy, each ring optionally substituted by halogen, (C.sub.1 -C.sub.3) alkyl or (C.sub.1 -C.sub.3) haloalkyl, (C.sub.4 -C.sub.8) trialkylsilylalkyl, (C.sub.3 -C.sub.8) cyanoalkyl, (C.sub.3 -C.sub.8) halocycloalkyl, (C.sub.3 -C.sub.8) haloalkenyl, (C.sub.5 -C.sub.8) alkoxyalkenyl, (C.sub.5 -C.sub.8) haloalkoxyalkenyl, (C.sub.5 -C.sub.8) alkylthioalkenyl, (C.sub.3 -C.sub.8) haloalkinyl, (C.sub.5 -C.sub.8) alkoxyalkinyl, (C.sub.5 -C.sub.8) haloalkoxyalkinyl, (C.sub.5 -C.sub.8) alkylthioalkinyl, (C.sub.2 -C.sub.8) alkylcarbonyl, benzyl, optionally substituted by halogen, (C.sub.1 -C.sub.3) alkyl or (C.sub.1 -C.sub.3) haloalkyl, CHR.sup.19 COR.sup.13, CHR.sup.19 P(O)(OR.sup.13).sub.2, CHR.sup.19 P(S)(OR.sup.13).sub.2, P(O)(OR.sup.13).sub.2, P(S) (OR.sup.13).sub.2, CHR.sup.19 C(O)NR.sup.14 R.sup.15, CHR.sup.19 C(O)NH.sub.2, CHR.sup.19 CO.sub.2 R.sup.13, CO.sub.2 R.sup.13, SO.sub.2 R.sup.13, phenyl, optionally substituted by R.sup.24, ##STR40## R.sup.13 =(C.sub.1 -C.sub.6) alkyl, (C.sub.1 -C.sub.6) haloalkyl, (C.sub.3 -C.sub.6) alkenyl or (C.sub.3 -C.sub.6) alkinyl,
• R.sup.14 and R.sup.16 =independently of one another, H or (C.sub.1 -C.sub.4) alkyl,
• R.sup.15 and R.sup.17 =independently of one another, (C.sub.1 -C.sub.4) alkyl or phenyl, optionally substituted by halogen, (C.sub.1 -C.sub.3) alkyl or (C.sub.1 -C.sub.3) haloalkyl, or
• R.sup.14 and R.sup.15 can, together with the nitrogen atom that binds them, form a piperidinyl-, pyrrolidinyl- or morpholinyl-ring, each ring optionally substituted by (C.sub.1 -C.sub.3) alkyl, phenyl or benzyl, or
• R.sup.16 and R.sup.17 can, together with the carbon atom that binds them, be (C.sub.3 -C.sub.8) cycloalkyl, R.sup.18 =(C.sub.1 -C.sub.4) alkyl or (C.sub.1 -C.sub.4) haloalkyl,
• R.sup.19 and R.sup.20 =independently H or (C.sub.1 -C.sub.5) alkyl,
• R.sup.21 =H, (C.sub.1 -C.sub.6) alkyl, (C.sub.3 -C.sub.6) alkenyl or (C.sub.3 -C.sub.6) alkinyl,
• R.sup.22 and R.sup.27 =independently of one another, H, (C.sub.1 -C.sub.4) alkyl or halogen, or
• R.sup.12 and R.sup.22 can together form a (C.sub.2 -C.sub.3) alkylen,
• R.sup.23, R.sup.24 and R.sup.28 =independently of one another, H or (C.sub.1 -C.sub.4) alkyl,
• R.sup.25 =(C.sub.1 -C.sub.2) alkyl, (C.sub.1 -C.sub.2) haloalkyl, OCH.sub.3, SCH.sub.3, OCHF.sub.2, halogen, CN or NO.sub.2 and
• R.sup.26 =H, (C.sub.1 -C.sub.5) alkyl, (C.sub.1-C.sub.5) haloalkyl, (C.sub.3 -C.sub.6) cycloalkyl, (C.sub.3 -C.sub.6) halocycloalkyl, (C.sub.1 -C.sub.5) alkoxy, (C.sub.1-C.sub.5) haloalkoxy and phenyl, that may optionally be substituted up to three times optionally by halogen, NO.sub.2, cyano, (C.sub.1 -C.sub.2) alkyl, (C.sub.1 -C.sub.2) haloalkyl, (C.sub.1 -C.sub.2) alkoxy or (C.sub.1 -C.sub.2) haloalkoxy,
• R.sup.29 =H, halogen or (C.sub.1 -C.sub.6) alkyl,
• R.sup.30 =H, (C.sub.1 -C.sub.4) alkyl or halogen,
• wherein amides of formula (IV) ##STR41## wherein R.sup.1, R.sup.2 and R.sup.3 have the meaning given above are reacted with phosgen or thiophosgen or a phosgen substitute or thiophosgen substitute optionally in a solvent to a compound of formula (V) ##STR42## wherein R.sup.1, R.sup.2 and R.sup.3 and X have the meaning given above and these compounds of formula (V) are then reacted with a compound of formula (VI) or an acid addition salt thereof,
• Q--NH--NH--CO--R.sup.26 (VI)
• wherein Q and R.sup.2.sup.26 have the meaning given above optionally in the presence of a diluting agent and optionally initially in the presence of a base and then in the presence of an acid and optionally by increasing the temperature to a compound of formulae (I) or (II).