Arthropodicidal fused tetrahydropyridazines

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...

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514 81, 514 85, 5142245, 5142302, 5142328, 5142332, 514247, 514248, 514252, 544 34, 544 95, 544101, 544115, 544229, 544232, 544233, 544234, 544238, 544239, 544240, 544241, 560 51, 562405, 562462, 568326, 568327, C07D23726, C07D491048, C07D48704, C07D49504

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053807189

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

1. Field of the Invention
Insecticidal tetrahydropyridazines, compositions containing them and methods for controlling arthropods employing them.
2. State of the Art
Vaughan, J. Org. Chem., 20 (1955), pages 1619 to 1626, discloses 1,5-diphenyl-2-pyrazoline-3-carboxamide.
U.S. Pat. No. 4,070,365 discloses insecticidal compounds of the formula: ##STR2## wherein X is halogen; and Y is halogen, NO.sub.2 or alkyl.
EP 153,127 discloses insecticidal compounds of the formula: ##STR3## wherein A is unsubstituted or substituted phenyl; B is unsubstituted or substituted phenyl; U is O, S or NR; and R, Y and Z are broadly defined.
Harhash et al., J. Heterocyclic Chem., 21 (1984), at page 1013, discloses the preparation of pyrazoline compounds: ##STR4## where R/Ar are C.sub.6 H.sub.5 /C.sub.6 H.sub.5 ; CO.sub.2 C.sub.2 H.sub.5 /C.sub.6 H.sub.5 ; C(O)NHC.sub.6 H.sub.5 /C.sub.6 H.sub.5 ; CH.dbd.CHC.sub.6 H.sub.5 /C.sub.6 H.sub.5 ; and CH.sub.3 /4-NO.sub.2 -C.sub.6 H.sub.4.
J. Org. Chem., 1987, 52, 2277 discloses pyrazolidines as does Chem. Soc. Jap., 55, 2450 (1982).
EPA 330,678 EPA 322,168, WO 88/07994, WO 88/05046, WO 89/00562 and WO 90/03378 disclose insecticidal pyrazolines.


SUMMARY OF THE INVENTION

The invention pertains to compounds of Formulae I and II, including all geometric and stereoisomers, agriculturally suitable salts thereof, agricultural compositions containing them and their use for the control of arthropods in both agronomic and nonagronomic uses. The compounds are: ##STR5## wherein:
Q is selected from the group ##STR6##
A is H; --S--, --SO--, --SO.sub.2 --, --NR.sup.11 --, --OCH.sub.2 --, --SCH.sub.2 --, --N(R.sup.11)CH.sub.2 --, substituted --CH.sub.2 --, and substituted --CH.sub.2 CH.sub.2 --, the substituents independently selected from 1-2 halogen and 1-2 methyl; provided that when V is --OCH.sub.2 --, --SCH.sub.2 -- or --N(R.sup.11)CH.sub.2 --, either atom can be attached to the aromatic moiety; ##STR7## X is selected from the group O, S and N-X.sup.2 ; X.sup.1 is selected from the group Cl, Br, OR.sup.12, SR.sup.12 and NR.sup.12 R.sup.13 ; R.sup.12, SO.sub.2 Ph, OC(O)NR.sup.13 R.sup.14, OC(O)OR.sup.12, NR.sup.13 R.sup.14 and phenyl optionally subtituted with R.sup.15 ; substituted by W, C.sub.2 -C.sub.6 alkoxyalkyl, CHO, C.sub.2 -C.sub.6 alkylcarbonyl, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.2 -C.sub.6 haloalkylcarbonyl, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 haloalkylthio, phenylthio, R.sup.16 OC(O)NR.sup.17 S- and R.sup.18 (R.sup.19)NS-; -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylthioalkyl, C.sub.1 -C.sub.6 nitroalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, phenyl optionally substituted with 1 to 3 substituents independently selected from W, benzyl optionally substituted with 1 to 3 substituents independently selected from W, halogen, CN, N.sub.3, SCN, NO.sub.2, OR.sup.21, SR.sup.21, S(O)R.sup.21, S(O).sub.2 R.sup.21, OC(O)R.sup.21, OS(O).sub.2 R.sup.21, CO.sub.2 R.sub.21, C(O)R.sup.21, C(O)NR.sup.21 R.sup.22, SO.sub.2 NR.sup.21 R.sup.22, NR.sup.21 R.sup.22, NR.sup.22 C(O)R.sup.21, OC(O)NHR.sup. 21, NR.sup.22 C(O)NHR.sup.21 and NR.sup.22 SO.sub.2 R.sup.21 ; or when m, n or p is 2, (R.sup.1).sub.2 when attached to adjacent atoms can be taken together, or (R.sup.2).sub.2 when attached to adjacent atoms can be taken together, or (R.sup.20).sub.2 when attached to adjacent atoms can be taken together as --OCH.sub.2 O--, --OCF.sub.2 O--, --OCH.sub.2 CH.sub.2 O--, --CH.sub.2 C(CH.sub.3).sub.2 O--, --CF.sub.2 CF.sub.2 O-- or --OCF.sub.2 CF.sub.2 O-- to form a cyclic bridge; provided that when R.sup.1, R.sup.2 or R.sup.20 is S(O)R.sup.21, S(O).sub.2 R.sup.21, OC(O)R.sup.21 or OS(O).sub.2 R.sup.21 then R.sup.21 is other than H; N(R.sup.26)R.sup.27, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 hal

REFERENCES:
patent: 4070365 (1978-01-01), van Daalen et al.
patent: 4602019 (1986-07-01), Sircar et al.
Hagiwara et al, Chemical Abstractsl , vol. 115, No. 208008 (1991) (Abstract of JP 03161478, Jul. 11, 1991).
W. R. Vaughan, J. Org. Chem. 20:1619-1626 (1955).
H. M. Hassaneen et al., J. Heterocyclic Chem. 21:1013-1016 (Jul.-Aug. 1984).
Shabarov et al Chem. Abstracts, 68(19):86912n (1968).
Levina et al Chem. Abstracts 54:19544f (1960).
Rudenro Chem. Abstrqacts, 55:25808g (1961).
Shabarov et al. Chem. Abstracts, 55:12418f (1961).
T. Shimizu, J. Org. Chem. 52:2277 (1987).
T. Shimizu, Chem. Soc. Jap., 55:2450 (1982).
Tomita et al, J. Het. Chem. 27, pp. 707-710 (1990).

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