Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-06-18
1995-10-31
Gupta, Yogendra N.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
5142302, 544 66, 544 67, 544 68, A61K 31535, C07D27304
Patent
active
054629381
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
Arthropodicidal carboxanilides, compositions containing them, and use of the carboxanilides to control arthropods. Relevant to this invention are WO 88/07,994 and EPA 330,678 which disclose insecticidal pyrazolines and WO 90/07495 which discloses insecticidal semicarbazone arthropodicides.
SUMMARY OF THE INVENTION
The invention pertains to compounds of Formula 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 non-agronomic uses. The term "compounds" will be understood to include all such isomers and salts thereof. The compounds are: ##STR3## wherein: Q is selected from the group ##STR4## A is H; E is selected from the group H and C.sub.1 -C.sub.3 alkyl; or --, --O--, --S--, --S(O)--, --S(O).sub.2 --, --NR.sup.7 --, --OCH.sub.2 --, --SCH.sub.2 --, --N(R.sup.7)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; ##STR5## 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.8, SR.sup.8 and NR.sup.8 R.sup.9 ; R.sup.8, SO.sub.2 Ph, OC(O)NR.sup.9 R.sup.10, OC(O)OR.sup.8, NR.sup.9 R.sup.10 and phenyl optionally substituted with R.sup.11 ; -C.sub.6 alkoxyalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.1 -C.sub.6 alkyl optionally substituted by halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, CN, NO.sub.2, S(O).sub.r R.sup.32, COR.sup.32, CO.sub.2 R.sup.32, phenyl optionally substituted by halogen, CN, C.sub.1 -C.sub.2 haloalkyl and C.sub.1 -C.sub.2 haloalkoxy; C.sub.3 -C.sub.6 cycloalkyl; C.sub.3 -C.sub.6 cyclohaloalkyl; C.sub.3 -C.sub.6 cycloalkylalkyl; CHO; C.sub.2 -C.sub.6 alkylcarbonyl; C.sub.2 -C.sub.6 alkoxycarbonyl; C.sub.2 -C.sub.6 haloalkylcarbonyl; COR.sup.36 ; CO.sub.2 R.sup.36 ; C.sub.1 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 haloalkylthio; phenylthio; R.sup.12 OC(O)N(R.sup.13)S-- and R.sup.14 (R.sup.15) 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, halogen, CN, N.sub.3, SCN, NO.sub.2, OR.sup.17, SR.sup.17, S(O)R.sup.17, S(O).sub.2 R.sup.17, OC(O)R.sup.17, OS(O).sub.2 R.sup.17, CO.sub.2 R.sup.17, C(O)R.sup.17, C(O)NR.sup.17 R.sup.18, SO.sub.2 NR.sup.17 R.sup.18, NR.sup.17 R.sup.18, NR.sup.18 C(O)R.sup.17, OC(O)NHR.sup.17, NR.sup.18 C(O)NHR.sup.17, NR.sup.18 SO.sub.2 R.sup.17, phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W; or when m or n is 2, (R.sup.1).sub.2 can be taken together, or (R.sup.2).sub.2 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 or R.sup.2 is S(O)R.sup.17, S(O).sub.2 R.sup.17, OC(O)R.sup.17 or OS(O).sub.2 R.sup.17 then R.sup.17 is other than H; N(R.sup.22)R.sup.23, C(R.sup.34).dbd.N--O--R.sup.35, C.sub.1 -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.2 -C.sub.6 alkoxylalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, CO.sub.2 R.sup.17, OR.sup.19, C(O)R.sup.17, C(O)NR.sup.17 R.sup.18, C(S)NR.sup.17 R.sup.18, C(S)R.sup.17, C(S)SR.sup.17, CN, Si(R.sup.28) (R.sup.29) R.sup.27, SR.sup.27, S(O)R.sup.27, SO.sub.2 R.sup.27, --P(O) (OR.sup.27).sub.2, phenyl, phenyl substituted with (R.sup.16).sub.p, benzyl and benzyl substituted with 1 to 3 substituents independently selected from W; or R.sup.3 is C.sub.2 -C.sub.6 epoxyalkyl optionally su
REFERENCES:
patent: 4070365 (1978-01-01), van Daalen
patent: 4863947 (1989-09-01), Jacobson
patent: 5091405 (1992-02-01), Stevenson
Annus Gary D.
Barnette William E.
McCann Stephen F.
Wing Keith D.
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