Oxa-and thia(di)azabicyclic compounds

Details Oxa-and thia(di)azabicyclic compounds Oxa-and thia(di)azabicyclic compounds

1996-02-28

1998-01-27

McKane, Joseph

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

504221, 504225, 504266, 504263, 504267, 544 52, 544 66, 544105, 544133, 548126, 548154, 548159, 548161, C07D49802, A01N 43824

Patent

active

057122253

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to novel oxa(di)azabicyclic and thia(di)azabicyclic compounds, a method for their preparation and their use as weedkillers.
As has already been reported, certain thiadiazabicyclic compounds (see EP 238 711, EP 304 920, U.S. Pat. Nos. 4,885,023, 4,684,397, US 4,801,408, WO 92/21684 and EP 600 833) can be used as weedkillers.
The present invention provides novel compounds of Formula I, ##STR1## wherein: X is selected from the group O, S, S(O), S(O).sub.2, CH.sub.2, CHF, CF.sub.2, CHCl, CHBr, CHOCH.sub.2 F, CHOCHF.sub.2, CHOCF.sub.3, CHOCH.sub.2 CF.sub.3 and NR.sup.4 ; alkyl, cyano, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 haloalkylthio, C.sub.2 -C.sub.4 alkylcarbonyl, OR.sup.3, C.sub.2 -C.sub.6 alkyloxycarbonyl, C.sub.2 -C.sub.6 haloalkoxycarbonyl, and C.sub.3 -C.sub.8 alkoxycarbonylalkyl; or, two R.sup.A groups on the same carbon atom, together with this carbon, are C.dbd.O; C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkylcarbonyl and C.sub.2 -C.sub.4 haloalkylcarbonyl; C.sub.1 -C.sub.3 haloalkyl, C.sub.2 -C.sub.4 alkylcarbonyl, C.sub.2 -C.sub.4 haloalkoxycarbonyl and C.sub.2 -C.sub.4 alkoxycarbonyl; is halogen; and CF.sub.3, m and n are 1, and U is N, then p is 1 to 5 and at least one R.sup.A is other than alkyl; ##STR2## Z is O or S; R.sup.5 is hydrogen or halogen; haloalkyl, OCH.sub.3, SCH.sub.3, OCHF.sub.2, halogen, CN and NO.sub.2 ; C.sub.1 -C.sub.8 haloalkyl, halogen, OR.sup.11, SR.sup.11, S(O).sub.q R.sup.11, COR.sup.11, CO.sub.2 R.sup.11, C(O)SR.sup.11, C(O)NR.sup.12 R.sup.13, CHO and NHSO.sub.2 NHR.sup.16 ; C.sub.1 -C.sub.3 haloalkyl and halogen; C.sub.1 -C.sub.3 haloalkyl and halogen; or, when Q is Q-2 or Q-6, R.sup.8 and R.sup.9 together with the carbon to which they are bonded is additionally selected from C.dbd.O; -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.3 -C.sub.6 alkenyl and C.sub.3 -C.sub.6 alkenyl; -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkenyl, 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 alkylsulphinylalkyl, C.sub.2 -C.sub.8 alkylsulphonylalkyl, C.sub.3 -C.sub.8 alkoxyalkoxyalkyl, C.sub.4 -C.sub.8 cycloalkylalkyl, C.sub.2 -C.sub.4 carboxyalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, C.sub.6 -C.sub.8 alkenyloxycarbonylalkyl, C.sub.6 -C.sub.8 alkenyloxycarbonylalkyl, C.sub.5 -C.sub.8 alkoxycarbonylalkenyl, C.sub.4 -C.sub.8 alkenyloxyalkyl, C.sub.6 -C.sub.8 cycloalkoxyalkyl, C.sub.4 -C.sub.8 alkynyloxyalkyl, C.sub.3 -C.sub.8 haloalkoxyalkyl, C.sub.4 -C.sub.8 haloalkenyloxyalkyl, C.sub.4 -C.sub.8 haloalkynyloxyalkyl, C.sub.4 -C.sub.8 alkenylthioalkyl, C.sub.4 -C.sub.8 alkynylthioalkyl; C.sub.1 -C.sub.4 alkyl substituted with phenoxy or benzyloxy, each of the phenoxy and benzyloxy optionally substituted with at least one member independently selected from the group halogen, C.sub.1 -C.sub.3 alkyl and 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 haloalkynyl, C.sub.5 -C.sub.8 alkoxyalkynyl, C.sub.5 -C.sub.8 haloalkoxyalkynyl, C.sub.5 -C.sub.8 alkylthioalkynyl, C.sub.2 -C.sub.8 alkylcarbonyl; benzyl optionally substituted with at least one member independently selected from the group halogen, C.sub.1 -C.sub.3 alkyl and C.sub.1 -C.sub.3 haloalkyl; CHR.sup.17 COR.sup.18, CHR.sup.7 P(O)(ORI.sup.18).sub.2, P(O)(OR.sup.18).sub.2, CHR.sup.17 P(S)(OR.sup.18).sub.2, CHR.sup.17 C(O)NR.sup.12 R.sup.13, CHR.sup.17 C(O)NH.sub.2, phenyl and pyridyl, each of the phenyl and pyridyl optionally substituted with at least one member independently selected from the group halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.4 alkoxy and CHR.sup.17 CH.dbd.NOR.sup.18 ; -C.sub.4 alkyl and phenyl optionally substituted with at least one member independently selected from the group h

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