Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1993-02-16
1995-12-12
Ford, John M.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5483117, 5483565, 5483581, 5483585, 546256, 546271, 544238, 544331, 544298, 544405, 5483591, 514269, 514256, 514333, 514338, 514397, 514406, 514407, C07D40104, C07D40304, A01N 4356, A01N 4356
Patent
active
054749980
DESCRIPTION:
BRIEF SUMMARY
1. Field of the Invention
This invention concerns arthropodicidal pyrazolines, pyrazolidines and hydrazines, compositions containing them, and a method for their use to control arthropods.
2. State of the Art
WO 88/07,994 and EPA 330,678 disclose insecticidal pyrazolines. U.S. Pat. No. 4,547,524 discloses benzoyl hydrazone derivatives as insecticides. WO 88/00197 discloses substituted semicarbazones derived from chromanones and thiochromanones as insecticide intermediates. EP-3,913, EP 26,040 and EP 254,461 disclose substituted hydrazone insecticides. J. Org. Chem., 1987, 52, 2277 discloses pyrazolines as does Chem Soc., Jap., 55, 2450 (1982).
J. Ind. Chem. Soc., 37, pages 443 to 450 (1960) discloses a compound of the formula: ##STR2## but no utility therefor.
Vaughn, J. Org. Chem., 20 (1955), pages 1619 to 1626, discloses 1,5-diphenyl-2-pyrazoline-3-carboxamide. No utility is given for the disclosed compound which, in any event, does not suggest a compound of the instant invention.
Harhash et al., J. Heterocyclic Chem., 21 (1984), at page 1013, discloses the preparation of five pyrazoline compounds, none of which is disclosed in the instant application. No utility is given for any of said compounds: ##STR3## 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 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 ##STR4## wherein X is halogen; and Y is halogen, NO.sub.2 or alkyl.
EP 153,127 discloses insecticidal compounds of the formula ##STR5## wherein A is unsubstituted or substituted phenyl; B is unsubstituted or substituted phenyl; U is O, S or NR; Y is alkyl, unsubstituted or substituted phenyl, or C(X)G; Z is H, cycloalkyl, unsubstituted or substituted phenyl R.sup.4 --Q; X is O or S; and G and R.sup.4 --Q are broadly defined.
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 compounds are: ##STR6## wherein: Q is selected from the group ##STR7## A is selected from the group CH.sub.2, CH.sub.2 CH.sub.2, O, S, S(O), S(O).sub.2, N(R.sup.5), OCH.sub.2, SCH.sub.2, N(R.sup.5)CH.sub.2, substituted CH.sub.2, and substituted CH.sub.2 CH.sub.2, the substituents independently selected from 1-2 halogen and methyl; ##STR8## 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.6, SR.sup.6 and N(R.sup.6)R.sup.7 ; R.sup.6, SO.sub.2 Ph, OC(O)N(R.sup.7)R.sup.8, OC(O)OC.sub.1 --C.sub.6 alkyl, N(R.sup.7)R.sup.8 and phenyl optionally substituted with R.sup.9 ; alkyl, benzyl, 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.10 OC(O)N(R.sup.11)S-- and R.sup.12 (R.sup.13)NS--; 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.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.15, SR.sup.15, S(O)R.sup.15, S(O).sub.2 R.sup.15, OC(O)R.sup.15, OS(O).sub.2 R.sub.15, CO.sub.2 R.sup.15, C(O)R.sup.15, C(O)N(R.sup.15)R.sup.16, SO.sub.2 N(R.sup.15)R.sup.16, N(R.sup.15)R.sup.16, N(R.sup.16)C(O)R.sup.15, OC(O)NHR.sup.15, N(R.sup.16)C(O)NHR.sup.15, N(R.sup.16)SO.sub.2 R.sup.15, 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, n or p is 2, (R.sup.1).s
Harrison Charles R.
Lett Renee M.
McCann Stephen F.
Shapiro Rafael
Stevenson Thomas M.
E. I. Du Pont de Nemours and Company
Ford John M.
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