Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1990-05-21
1992-05-26
Fan, Jane T.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514247, 514403, 514255, 514256, 514365, 514374, 514397, 546279, 548379, 548236, 548204, 548336, 544238, 544333, 544405, A61K 3144, C07D40104
Patent
active
051168502
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
Compounds and compositions comprising heterocyclic pyrazoline carboxanilides having a >N--N.dbd.C--C(O or S)--N< backbone.
J. Org. Chem., 20, page 1619 (1955) discloses 1,5-diphenyl-2-pyrazoline-3-carboxamide. No utility is presented. Harhash et al., J. Heterocyclic Chem., 21, page 1013 (1984), disclose the preparation of these five pyrazolines for which no utility is presented: ##STR1## 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.
U.S. Pat. No. 4,070,365 discloses insecticidal compounds of the formula ##STR2## where R.sub.1 is optionally substituted phenyl; R.sub.2 and R.sub.3 are independently optionally substituted pyridyl, thienyl or phenyl groups and X is O or S.
EPA 0153127 discloses insecticidal compounds of the formula ##STR3## wherein A and B are unsubstituted or substituted aryl; U is O, S or NR; Y is alkyl, carbonyl or unsubstituted or substituted aryl, and Z is cycloalkyl or an unsubstituted or substituted aryl group.
PCT International Publication No. WO88/05046 discloses pyrazoline insecticides of the formula ##STR4## wherein: A is H, C.sub.1 to C.sub.6 alkyl, phenyl, phenyl substituted by (R.sub.5).sub.p, CN, CO.sub.2 R.sub.3, C(O)R.sub.3, C(O)NR.sub.3 R.sub.4, C(S)NR.sub.3 R.sub.4, C(S)R.sub.3 or C(S)SR.sub.3 ; C.sub.6 alkoxyalkyl, C.sub.2 to C.sub.6 cyanoalkyl, C.sub.3 to C.sub.8 alkoxycarbonylalkyl, C.sub.2 to C.sub.6 alkenyl, C.sub.2 to C.sub.6 alkynyl, C.sub.2 to C.sub.6 alkoxycarbonyl, phenyl, phenyl substituted with 1 to 3 substituents independently selected from W, benzyl or benzyl substituted with 1 to 3 substituents independently selected from W.
SUMMARY OF THE INVENTION
This invention pertains to compounds of Formula I, including all geometric and stereoisomers thereof, agriculturally suitable salts thereof, agricultural compositions containing said compounds and salts, and their use as insecticides: ##STR5## wherein: X is O or S; C.sub.4 alkoxyalkyl, C.sub.1 to C.sub.4 alkylthio, C.sub.1 to C.sub.4 haloalkylthio, SX', phenylthio, or phenylthio substituted with 1 to 3 substituents independently selected from W, C.sub.2 to C.sub.4 alkoxycarbonyl, C(O)H, C.sub.2 to C.sub.4 alkylcarbonyl and C.sub.2 to C.sub.4 haloalkylcarbonyl; substituted by (R.sub.5).sub.p, CN, CO.sub.2 R.sub.3, C(O)R.sub.3, C(O)NR.sub.3 R.sub.4, C(S)NR.sub.3 R.sub.4, C(S)R.sub.3, C(S)SR.sub.3 and J; C.sub.6 haloalkyl, C.sub.2 to C.sub.6 alkoxyalkyl, C.sub.2 to C.sub.6 cyanoalkyl, C.sub.3 to C.sub.8 alkoxycarbonylalkyl, C.sub.2 to C.sub.6 alkenyl, C.sub.2 to C.sub.6 alkynyl, C.sub.2 to C.sub.6 alkoxycarbonyl, phenyl, phenyl substituted with 1 to 3 substituents independently selected from W, benzyl and benzyl substituted with 1 to 3 substituents independently selected from W; alkyl, C.sub.1 to C.sub.2 haloalkyl, C.sub.1 to C.sub.2 alkoxy, C.sub.1 to C.sub.2 haloalkoxy, C.sub.1 to C.sub.2 alkylthio, C.sub.1 to C.sub.2 haloalkylthio, C.sub.1 to C.sub.2 alkylsulfonyl and C.sub.1 to C.sub.2 haloalkylsulfonyl; ##STR6## or K, being K when A is other than J; R.sub.1, R.sub.2 and R.sub.5 are independently selected from the group R.sub.3, halogen, CN, N.sub.3, SCN, NO.sub.2, OR.sub.3, SR.sub.3, S(O)R.sub.3, S(O).sub.2 R.sub.3, OC(O)R.sub.3, OS(O).sub.2 R.sub.3, CO.sub.2 R.sub.3, C(O)R.sub.3, C(O)NR.sub.3 R.sub.4, S(O).sub.2 NR.sub.3 R.sub.4, NR.sub.3 R.sub.4, NR.sub.4 C(O)R.sub.3, OC(O)NHR.sub.3, NR.sub.4 C(O)NHR.sub.3, NR.sub.4 S(O).sub.2 R.sub.3, and when m, n or p is 2, R.sub.1, R.sub.2 or R.sub.5 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--, --OCF.sub.2 CF.sub.2 O--, or --CF.sub.2 CF.sub.2 O-- to form a 5- or 6-membered ring; C.sub.4 haloalkyl, C.sub.2 to C.sub.4 alkenyl, C.sub.2 to C.sub.4 haloalkenyl, C.sub.2 to C.sub.4 alkynyl, C.sub.2 to C.sub.4 haloalkynyl, C.sub.2 to C.sub.4 alkoxyalkyl, C.sub.2 to C.sub.4 alkylthioalkyl, C.sub.1 to C.
REFERENCES:
patent: 4070365 (1978-01-01), Van Daalen et al.
patent: 4174393 (1979-11-01), Van Daalen et al.
patent: 4767779 (1988-08-01), Duggan
patent: 4837220 (1989-06-01), Neh et al.
patent: 4888340 (1989-12-01), Neh et al.
Vaughan Jan. Org. Chem. vol. 20, 1955, pp. 1619-1926.
Costello James A.
E. I. du Pont de Nemours and Co.
Fan Jane T.
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