Back to results
US 5,686,393 AGranted
Arthropodicidal oxazolines and thiazolines
AssigneeE. I. Du Pont de Nemours and Company
InventorsGeorge Philip Lahm, Thomas Martin Stevenson
Life of this patent
Estimating the term…
Abstract
Described herein are arthropodicidal compounds, compositions and use of compounds of Formula (I) wherein the substituents are defined in the disclosure ##STR1##
Claims11
A compound of the formula ##STR18## wherein:
- E is selected from the group C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 haloalkyl;
- Z is selected from the group O and S;
- R.sup.1 is selected from the group F and Cl;
- R.sup.2 is selected from the group H, F and Cl;
- R.sup.3 is selected from the group C.sub.2 -C.sub.10 alkynyl optionally substituted with at least one member independently selected from R.sup.9 ;
- OR.sup.12 ;
- phenyl substituted with at least one member independently selected from W.sup.1 ;
- and an 8- to 12-membered fused bicyclic ring system containing 0-4 heteroatoms independently selected from 0-4 nitrogen, 0-2 oxygen and 0-2 sulfur, the ring system optionally substituted with at least one member independently selected from W;
- R.sup.4 and R.sup.5 are independently selected from the group H, halogen, CN, NO.sub.2, C.sub.1 -C.sub.16 alkyl, C.sub.1 -C.sub.16 alkoxy, C.sub.1 -C.sub.16 haloalkyl, C.sub.1 -C.sub.16 haloalkoxy, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.16 cycloalkylalkyl, C.sub.2 -C.sub.16 alkenyl, C.sub.2 -C.sub.16 haloalkenyl, C.sub.2 -C.sub.16 alkynyl, C.sub.2 -C.sub.16 haloalkynyl, C.sub.2 -C.sub.16 alkoxyalkoxy, Si(R.sup.6)(R.sup.7)R.sup.8, and phenyl optionally substituted with at least one member independently selected from W;
- R.sup.6, R.sup.7 and R.sup.8 are independently selected from C.sub.1 -C.sub.6 alkyl;
- R.sup.9 is selected from the group phenyl and pyridyl, each optionally substituted with at least one member independently selected from W;
- R.sup.12 is selected from the group tetrahydropyranyl;
- C.sub.1 -C.sub.10 alkyl substituted with at least one member independently selected from the group CN, C.sub.2 -C.sub.6 alkylcarbonyl, C.sub.2 -C.sub.6 haloalkylcarbonyl, C.sub.2 -C.sub.6 haloalkoxycarbonyl, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.2 -C.sub.6 alkylcarbonyl, and Si(R.sup.6)(R.sup.7)R.sup.8 ;
- C.sub.3 -C.sub.7 cycloalkyl;
- C.sub.3 -C.sub.7 halocycloalkyl;
- C.sub.3 -C.sub.7 cyanocycloalkyl;
- C.sub.4 -C.sub.7 alkylcycloalkyl;
- C.sub.4 -C.sub.7 cycloalkylalkyl;
- C.sub.4 -C.sub.7 halocycloalkylalkyl;
- C.sub.3 -C.sub.10 haloalkynyl;
- C.sub.2 -C.sub.10 haloalkenyl optionally substituted with at least one member independently selected from the group CN and C.sub.2 -C.sub.6 alkoxycarbonyl;
- and an 8- to 12-membered fused bicyclic ring system containing 0-4 heteroatoms independently selected from 0-4 nitrogen, 0-2 oxygen and 0-2 sulfur, the ring system optionally substituted with at least one member independently selected from W;
- R.sup.13 is selected from the group C.sub.1 -C.sub.3 alkyl and C.sub.1 -C.sub.3 haloalkyl;
- W is selected from the group halogen, CN, CHO, NO.sub.2, SF.sub.5, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, C.sub.2 -C.sub.4 alkylcarbonyl and C.sub.2 -C.sub.4 alkoxycarbonyl;
- W.sup.1 is selected from the group CN, CHO, NO.sub.2, SF.sub.5, S(O).sub.n R.sup.13, C.sub.2 -C.sub.4 alkylcarbonyl, and C.sub.2 -C.sub.4 alkoxycarbonyl;
- n is 0, 1 or 2;
- and
- q is0, 1, 2or3.
25 more elements
An arthropodicidal composition comprising an arthropodicidally effective amount of a compound of the formula ##STR19## wherein:
- A is selected from the group a direct bond and C.sub.1 -C.sub.3 straight or branched chain alkylene;
- E is selected from the group C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 haloalkyl;
- Z is selected from the group O and S;
- R.sup.1 and R.sup.2 are independently selected from the group H, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 alkylthio, CN and NO.sub.2 ;
- R.sup.3 is selected from the group C.sub.3 -C.sub.7 halocycloalkyl;
- C.sub.2 -C.sub.10 haloalkenyl optionally substituted with a group selected from CN and C.sub.2 -C.sub.6 alkoxycarbonyl;
- C.sub.1 -C.sub.10 alkyl substituted with at least one member independently selected from the group Si(R.sup.6)(R.sup.7)R.sup.8, CN, C.sub.2 -C.sub.6 alkylcarbonyl, C.sub.2 -C.sub.6 haloalkylcarbonyl, C.sub.2 -C.sub.6 haloalkoxycarbonyl, and C.sub.2 -C.sub.6 alkoxycarbonyl;
- C.sub.2 -C.sub.6 alkylcarbonyl;
- C.sub.2 -C.sub.10 alkenyl optionally substituted with at least one member independently selected from R.sup.9 ;
- C.sub.2 -C.sub.10 alkynyl optionally substituted with at least one member independently selected from R.sup.9 ;
- C.sub.2 -C.sub.6 haloalkylcarbonyl;
- C.sub.2 -C.sub.6 alkoxycarbonyl;
- C.sub.2 -C.sub.6 haloalkoxycarbonyl;
- C(O)R.sup.9 ;
- C(O)OR.sup.9 ;
- C(O)N(R.sup.10)R.sup.11 ;
- OR.sup.12 ;
- tetrahydropyranyl;
- phenyl substituted with at least one member independently selected from W.sup.1 ;
- and an 8- to 12-membered fused bicyclic ring system containing 0-4 heteroatoms independently selected from 0-4 nitrogen, 0-2 oxygen and 0-2 sulfur, the ring system optionally substituted with at least one member independently selected from W;
- R.sup.4 and R.sup.5 are independently selected from the group H, halogen, CN, NO.sub.2, C.sub.1 -C.sub.16 alkyl, C.sub.1 -C.sub.16 alkoxy, C.sub.1 -C.sub.16 haloalkyl, C.sub.1 -C.sub.16 haloalkoxy, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.16 cycloalkylalkyl, C.sub.2 -C.sub.16 alkenyl, C.sub.2 -C.sub.16 haloalkenyl,
- C.sub.2 -C.sub.16 alkynyl, C.sub.2 -C.sub.16 haloalkynyl, C2-C16 alkoxyalkoxy, Si(R.sup.6)CR.sup.7)R.sup.8, and phenyl optionally substituted with at least one member independently selected from W;
- R.sup.6, R.sup.7 and R.sup.8 are independently selected from C.sub.1 -C.sub.6 alkyl;
- R.sup.9 is selected from the group phenyl and pyridyl, each optionally substituted with at least one member independently selected from W;
- R.sup.10 and R.sup.11 are independently selected from the group H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, and phenyl optionally substituted with at least one member independently selected from W;
- R.sup.12 is selected from the group tetrahydropyranyl;
- C.sub.1 -C.sub.10 alkyl substituted with at least one member independently selected from the group CN, C.sub.2 -C.sub.6 alkylcarbonyl, C.sub.2 -C.sub.6 haloalkylcarbonyl, C.sub.2 -C.sub.6 haloalkoxycarbonyl, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.2 -C.sub.6 alkylcarbonyl, and Si(R.sup.6)(R.sup.7)R.sup.8 ;
- C.sub.3 -C.sub.7 cycloalkyl;
- C.sub.3 -C.sub.7 halocycloalkyl;
- C.sub.3 -C.sub.7 cyanocycloalkyl;
- C.sub.4 -C.sub.7 alkylcycloalkyl;
- C.sub.4 -C.sub.7 cycloalkylalkyl;
- C.sub.4 -C.sub.7 halocycloalkylalkyl;
- C.sub.3 -C.sub.10 haloalkynyl;
- C.sub.2 -C.sub.10 haloalkenyl optionally substituted with at least one member independently selected from the group CN and C.sub.2 -C.sub.6 alkoxycarbonyl;
- and an 8- to 12-membered fused bicyclic ring system containing 0-4 heteroatoms independently selected from 0-4 nitrogen, 0-2 oxygen and 0-2 sulfur, the ring system optionally substituted with at least one member independently selected from W;
- R.sup.13 is selected from the group C.sub.1 -C.sub.3 alkyl and C.sub.1 -C.sub.3 haloalkyl;
- W is selected from the group halogen, CN, CHO, NO.sub.2, SF.sub.5, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, C.sub.2 -C.sub.4 alkylcarbonyl and C.sub.2 -C.sub.4 alkoxycarbonyl;
- W.sup.1 is selected from the group CN, CHO, NO.sub.2, SF.sub.5, S(O).sub.n R.sup.13, C.sub.2 -C.sub.4 alkylcarbonyl, and C.sub.2 -C.sub.4 alkoxycarbonyl;
- n is 0, 1 or 2;
- and
- q is 0, 1, 2 or 3;
- and a carrier therefor.
40 more elements
A method for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of a compound of the formula ##STR20## wherein:
- A is selected from the group a direct bond and C.sub.1 -C.sub.3 straight or branched chain alkylene;
- E is selected from the group C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 haloalkyl;
- Z is selected from the group O and S;
- R.sup.1 and R.sup.2 are independently selected from the group H, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 alkylthio, CN and NO.sub.2 ;
- R.sup.3 is selected from the group C.sub.3 -C.sub.7 halocycloalkyl;
- C.sub.2 -C.sub.10 haloalkenyl optionally substituted with a group selected from CN and C.sub.2 -C.sub.6 alkoxycarbonyl;
- C.sub.1 -C.sub.10 alkyl substituted with at least one member independently selected from the group Si(R.sup.6)(R.sup.7)R.sup.8, CN, C.sub.2 -C.sub.6 alkylcarbonyl, C.sub.2 -C.sub.6 haloalkylcarbonyl, C.sub.2 -C.sub.6 haloalkoxycarbonyl, and C.sub.2 -C.sub.6 alkoxycarbonyl;
- C.sub.2 -C.sub.6 alkyl carbonyl;
- C.sub.2 -C.sub.10 alkenyl optionally substituted with at least one member independently selected from R.sup.9 ;
- C.sub.2 -C.sub.10 alkynyl optionally substituted with at least one member independently selected from R.sup.9 ;
- C.sub.2 -C.sub.6 haloalkylcarbonyl;
- C.sub.2 -C.sub.6 alkoxycarbonyl;
- C.sub.2 -C.sub.6 haloalkoxycarbonyl;
- C(O)R.sup.9 ;
- C(O)OR.sup.9 ;
- C(O)N(R.sup.10)R.sup.11 ;
- OR.sup.12 ;
- tetrahydropyranyl;
- phenyl substituted with at least one member independently selected from W.sup.1 ;
- and an 8- to 12-membered fused bicyclic ring system containing 0-4 heteroatoms independently selected from 0-4 nitrogen, 0-2 oxygen and 0-2 sulfur, the ring system optionally substituted with at least one member independently selected from W;
- R.sup.4 and R.sup.5 are independently selected from the group H, halogen, CN, NO.sub.2, C.sub.1 -C.sub.16 alkyl, C.sub.1 -C.sub.16 alkoxy, C.sub.1 -C.sub.16 haloalkyl, C.sub.1 -C.sub.16 haloalkoxy, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.16 cycloalkylalkyl, C.sub.2 -C.sub.16 alkenyl, C.sub.2 -C.sub.16 haloalkenyl, C.sub.2 -C.sub.16 alkynyl, C.sub.2 -C.sub.16 haloalkynyl, C.sub.2 -C.sub.16 alkoxyalkoxy, Si(R.sup.6)(R.sup.7)R.sup.8, and phenyl optionally substituted with at least one member independently selected from W;
- R.sup.7 and R.sup.8 are independently selected from C.sub.1 -C.sub.6 alkyl;
- R.sup.9 is selected from the group phenyl and pyridyl, each optionally substituted with at least one member independently selected from W;
- R.sup.10 and R.sup.11 are independently selected from the group H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, and phenyl optionally substituted with at least one member independently selected from W;
- R.sup.12 is selected from the group tetrahydropyranyl;
- C.sub.1 -C.sub.10 alkyl substituted with at least one member independently selected from the group CN, C.sub.2 -C.sub.6 alkylcarbonyl, C.sub.2 -C.sub.6 haloalkylcarbonyl, C.sub.2 -C.sub.6 haloalkoxycarbonyl, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.2 -C.sub.6 alkylcarbonyl, and Si(R.sup.6)(R.sup.7)R.sup.8 ;
- C.sub.3 -C.sub.7 cycloalkyl;
- C.sub.3 -C.sub.7 halocycloalkyl;
- C.sub.3 -C.sub.7 cyanocycloalkyl;
- C.sub.4 -C.sub.7 alkylcycloalkyl;
- C.sub.4 -C.sub.7 cycloalkylalkyl;
- C.sub.4 -C.sub.7 halocycloalkylalkyl;
- C.sub.3 -C.sub.10 haloalkynyl;
- C.sub.2 -C.sub.10 haloalkenyl optionally substituted with at least one member independently selected from the group CN and C.sub.2 -C.sub.6 alkoxycarbonyl;
- and an 8- to 12-membered fused bicyclic ring system containing 0-4 heteroatoms independently selected from 0-4 nitrogen, 0-2 oxygen and 0-2 sulfur, the ring system optionally substituted with at least one member independently selected from W;
- R.sup.13 is selected from the group C.sub.1 -C.sub.3 alkyl and C.sub.1 -C.sub.3 haloalkyl;
- W is selected from the group halogen, CN, CHO, NO.sub.2, SF.sub.5, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, C.sub.2 -C.sub.4 alkylcarbonyl and C.sub.2 -C.sub.4 alkoxycarbonyl;
- W.sup.1 is selected from the group CN, CHO, NO.sub.2, SF.sub.5, S(O).sub.n R.sup.13, C.sub.2 -C.sub.4 alkylcarbonyl, and C.sub.2 -C.sub.4 alkoxycarbonyl;
- n is 0, 1 or 2;
- and
- q is0, 1, 2or3.
38 more elements
Dependencies are inferred from the claim text.