Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto
This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, compositions containing such molecules, and processes of using such molecules and compositions against such pests. These molecules and compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula (“Formula One”).
1. A molecule having the following formula
wherein:
(A) R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 9 , and R 10 are each independently selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , OH, (C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, and (C 3 -C 6 )cycloalkyl,
wherein each alkyl, alkenyl, haloalkyl, alkoxy, haloalkoxy, and cycloalkyl, are optionally substituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, CN, NO 2 , OH, (C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, and (C 3 -C 6 )cycloalkyl
(B) R 8 is H;
(C) L is selected from the group consisting of
(1) a bond connecting nitrogen to carbon in the ring, and
(2) a (C 1 -C 4 )alkyl wherein said alkyl is optionally substituted with one or more substituents independently selected from the group consisting of F, Cl, CN, OH, and oxo;
(D) R 11 and R 12 are each independently selected from the group consisting of H, (C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )alkenyloxy, (C 2 -C 4 )alkynyl, (C 2 -C 4 )alkynyloxy, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkoxy, (C 3 -C 6 )cycloalkenyl, (C 3 -C 6 )cycloalkenyloxy, ((C 1 -C 4 )alkyl)((C 3 -C 6 )cycloalkyl), C(O)((C 1 -C 4 )alkyl), ((C 1 -C 4 )alkyl)C(O)((C 1 -C 4 )alkyl), and ((C 1 -C 4 )alkyl)C(O)O((C 1 -C 4 )alkyl),
wherein each alkyl, alkenyl, alkenyloxy, alkynyl, alkynyloxy, haloalkyl, alkoxy, haloalkoxy, cycloalkyl, cycloalkoxy, cycloalkenyl, and cycloalkenyloxy, are optionally substituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, CN, NO 2 , OH, and oxo;
(E) R 13 is heterocyclyl, wherein said heterocyclyl is selected from the group consisting of dihydrofuranyl, furanyl, indazolyl, indolyl, imidazolyl, isoindolyl, isothiazolyl, isoxazolyl, oxadiazolyl, oxazolyl, pyrazolinyl, pyrazolyl, pyrrolyl, tetrazolyl, thiazolyl, thienyl, triazinyl, and triazolyl,
wherein each heterocyclyl is optionally substituted with one or more substituents independently selected from the group consisting of oxo, (C 1 -C 8 )alkyl, C(O)O(C 1 -C 4 )alkyl, phenyl, and pyridyl,
wherein each phenyl is optionally substituted with one or more substituents R, independently selected from the group consisting of F, Cl, Br, I, (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, and (C 1 -C 4 )haloalkoxy; and
(F) Q is selected from the group consisting of O and S; and
agriculturally acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, resolved stereoisomers, and tautomers, of the molecules of Formula One.
2. A molecule according to claim 1 wherein
(A) R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 9 , and R 10 are H;
(B) R 8 is H;
(C) L is selected from the group consisting of
(1) a bond connecting nitrogen to carbon in the ring, and
(2) a (C 1 -C 4 )alkyl;
(D) R 11 and R 12 are H;
(E) R 13 is heterocyclyl, wherein said heterocyclyl is selected from the group consisting of dihydrofuranyl, imidazolyl, isoxazolyl, oxadiazolyl, oxazolyl, pyrazolyl, thiazolyl, and thienyl,
wherein each heterocyclyl is optionally substituted with one or more substituents independently selected from the group consisting of oxo, (C 1 -C 8 )alkyl, C(O)O(C 1 -C 4 )alkyl, phenyl, and pyridyl,
wherein each phenyl is optionally substituted with one or more substituents R, independently selected from the group consisting of F, Cl, (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, and (C 1 -C 4 )haloalkoxy; and
(F) Q is selected from O and S.
3. A molecule according to claim 1 wherein said molecule is selected from the group consisting of
4. A molecule according to claim 1 wherein said molecule is selected from the group consisting of
5. A pesticidal composition comprising a molecule according to claim 1 , further comprising one or more active ingredients.
6. A pesticidal composition according to claim 5 wherein said active ingredient is selected from AIGA.
7. A pesticidal composition according to claim 5 wherein said active ingredient is selected from AI-1, 1,3-dichloropropene, chlorpyrifos, chlorpyrifos-methyl, hexaflumuron, methoxyfenozide, noviflumuron, spinetoram, spinosad, sulfoxaflor, and sulfuryl fluoride.
8. A pesticidal composition comprising a molecule according to claim 1 , further comprising a MoA Material.
9. A pesticidal composition according to claim 8 wherein said MoA Material is selected from MoAMGA.
10. A pesticidal composition according to claim 5 wherein the weight ratio of the molecule according to Formula One to said active ingredient is
(a) 100:1 to 1:100;
(b) 50:1 to 1:50;
(c) 20:1 to 1 to 20;
(d) 10:1 to 1:10;
(e) 5:1 to 1:5;
(f) 3:1 to 1:3;
(g) 2:1 to 1:2; or
(h) 1:1.
11. A process to control a pest said process comprising applying to a locus, a pesticidally effective amount of a molecule according to claim 1 .
12. A process to control a pest said process comprising applying to a locus, a pesticidally effective amount of a pesticidal composition according to claim 5 .
13. A molecule according to claim 1 wherein R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 are H, and R 5 is (C 1 -C 4 )haloalkoxy.
14. A molecule according to claim 13 wherein R 5 is OCF 3 or OCF 2 CF 3 .
15. A molecule according to claim 1 wherein L is a bond or L is —CH 2 CH 2 —.
16. A molecule according to claim 1 wherein R 13 is dihydrofuranyl, imidazolyl, isoxazolyl, oxadiazolyl, oxazolyl, pyrazolyl, thienyl, or thiazolyl that is substituted with one or more substituents selected from the group consisting of oxo, CH 3 , CH(CH 3 )CH 2 CH(CH 3 ) 2 , C(O)OCH 2 CH 3 , phenyl, and pyridyl that is further substituted with one or more substituents R, selected from F, Cl, CH 3 , CH 2 CH 3 , CH(CH 3 ) 2 , OCH 3 , and OCF 3 .