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US 5,182,303 AGranted
Substituted semicarbazone arthropodicides
AssigneeE. I. Du Pont de Nemours and Company
InventorsJohn P. Daub, George P. Lahm, Bradford S. Marlin
Life of this patent
Estimating the term…
Abstract
Certain substituted semicarbazones, including all geometric and stereoisomers thereof, agricultural compositions containing them and their use as arthropodicides.
Claims13
A compound of the formula ##STR28## wherein:
- Q is ##STR29## A is (CH.sub.2).sub.t, wherein, each carbon individually can be substituted with 1 to 2 substituents selected from 1 to 2 halogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, C.sub.4 -C.sub.7 alkylcycloalkyl, C.sub.2 -C.sub.4 alkoxycarbonyl, or phenyl optionally substituted with 1 to 3 substituent independently selected from W;
- R.sub.1 and R.sub.2 are independently R.sub.8, halogen, CN, NO.sub.2, N.sub.3, SCN, OR.sub.8, SR.sub.8, SOR.sub.8, SO.sub.2 R.sub.8, NR.sub.8 R.sub.9, C(O)R.sub.8, CO.sub.2 R.sub.8, C(O)NR.sub.8 R.sub.9, OC(O)R.sub.8, OCO.sub.2 R.sub.8, OC(O)NR.sub.8 R.sub.9, NR.sub.9 C(O)R.sub.8, NR.sub.9 C(O)NR.sub.8 R.sub.9, OSO.sub.2 R.sub.8, NR.sub.9 SO.sub.2 R.sub.8 ;
- R.sub.2 being other than CH.sub.3 when R.sub.1, R.sub.3 and R.sub.4 are H and A is CH.sub.2 ;
- R.sub.3 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.4 -C.sub.6 alkylcycloalkyl, 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 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, OR.sub.8, S(O).sub.q R.sup.8, NR.sub.8 R.sup.9, CN, CO.sub.2 R.sub.8, C(O)R.sub.8, C(O)NR.sub.8 R.sub.9, C(S)NR.sub.9 R.sup.9, C(S)R.sub.8, C(S)SR.sub.8, phenyl optionally substituted with (R.sub.10).sub.p or benzyl optionally substituted with 1 to 3 substituents independently selected from W or R.sub.3 is C.sub.3 -C.sub.6 cycloalkyl optionally substituted with 1 to 2 halogens or 1 to 2 CH.sub.3 ;
- R.sub.4 is H, 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 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 cyanoalkyl, phenyl optionally substituted with (R.sub.10).sub.p or benzyl optionally substituted with 1 to 3 substituents independently selected from W;
- R.sub.5 and R.sub.6 are independently H, C.sub.1 -C.sub.22 alkyl, C.sub.2 -C.sub.22 alkoxyalkyl, C.sub.2 -C.sub.22 alkylcarbonyl, C.sub.2 -C.sub.22 alkoxycarbonyl, C.sub.2 -C.sub.22 haloalkyl carbonyl, C.sub.2 -C.sub.22 haloalkoxycarbonyl, SR.sub.11, CHO, C.sub.1 -C.sub.4 alkylsulfonyl, phenylsulfonyl optionally substituted with 1 to 3 substituents independently selected from W;
- C.sub.7 -C.sub.15 phenoxycarbonyl optionally substituted with 1 to 3 substituents selected from W;
- C.sub.7 -C.sub.15 phenylcarbonyl optionally substituted with 1 to 3 substituents independently selected from W;
- C(O)CO.sub.2 C.sub.1 to C.sub.4 alkyl, C.sub.8 -C.sub.12 benzyloxycarbonyl optionally substituted with 1 to 3 substituents independently selected from W;
- or R.sub.5 and R.sub.6 are independently phenyl optionally substituted with 1 to 3 substituents independently selected from W, or benzyl optionally substituted with 1 to 3 substituents independently selected from W;
- R.sub.8 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl, C.sub.4 -C.sub.7 halocycloalkylalkyl 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 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 or benzyl optionally substituted with 1 to 3 substituents independently selected from W;
- R.sub.9 is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkynyl;
- R.sub.10 is R.sub.8, halogen, CN, NO.sub.2, N.sub.3, SCN, OR.sub.8, SR.sub.8, SOR.sub.8, SO.sub.2 R.sub.8, NR.sub.8 R.sub.9, COR.sub.8, CO.sub.2 R.sub.8, CONR.sub.8 R.sub.9, SO.sub.2 NR.sub.8 R.sub.9, OC(O)R.sub.8, OCO.sub.2 R.sub.8, OC(O)NR.sub.8 R.sub.9, NR.sub.9 C(O)R.sub.8, NR.sub.9 C(O)NR.sub.8 R.sub.9, OSO.sub.2 R.sub.8 or NR.sub.9 SO.sub.2 R.sub.8 ;
- R.sub.11 is C.sub.1 -C.sub.22 alkyl, C.sub.1 -C.sub.22 haloalkyl, phenyl optionally substituted with 1 to 3 substituents independently selected from W;
- W is halogen, CN, NO.sub.2, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 haloalkylthio, C.sub.1 -C.sub.2 alkylsulfonyl or C.sub.1 -C.sub.2 haloalkylsulfonyl;
- m is 1 to 5;
- n is 1 to 4;
- t is 0 to 3;
- when t is 2 and R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each H, then R.sub.1 is other than H or NO.sub.2 ;
- q is 0 to 2;
- p is 1 to 3;
- and
- X is O or S;
- X being O when A is CH.sub.2 and R.sub.2, R.sub.3 and R.sub.4 are H, with the further proviso that when X is S and A is CH.sub.2, the 2,3-dihydro-indene moiety may not be substituted solely with a single methyl group.
21 more elements
Dependencies are inferred from the claim text.