Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto

• US 10,251,394 B2
• Filed: 01/18/2017
• Issued: 04/09/2019
• Est. Priority Date: 01/25/2016
• Status: Active Grant

• Current Assignee: Corteva Agriscience LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Barton, Thomas, Gao, Xin, Hunter, Jim, LePlae, Jr., Paul R., Lo, William C., Boruwa, Joshodeep, Tangirala, Raghuram, Watson, Gerald B., Herbert, John
• Primary Examiner(s): Haghighatian, Mina
• Assistant Examiner(s): Hirt, Erin E
• Application Number:
  US15/408,604
• Publication Number:
  US 20170208803A1
• Time in Patent Office: 811 Days
• Field of Search: None
• CPC Class Codes: A01N 37/18 containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
• CPC Class Codes: A01N 37/34 Nitriles
• CPC Class Codes: A01N 43/36 five-membered rings
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/80 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• CPC Class Codes: A01N 47/24 containing the groups , or; Thio analogues thereof
• CPC Class Codes: A01N 53/00 Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
• CPC Class Codes: A61P 33/14 Ectoparasiticides, e.g. scabicides
• CPC Class Codes: C07C 233/65 having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
• CPC Class Codes: C07C 233/66 having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
• CPC Class Codes: C07C 233/76 having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
• CPC Class Codes: C07C 233/81 having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
• CPC Class Codes: C07C 233/83 of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 237/22 having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated peptides C07K
• CPC Class Codes: C07C 237/24 having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
• CPC Class Codes: C07C 243/34 to carbon atoms of a carbon skeleton further substituted by nitrogen atoms
• CPC Class Codes: C07C 255/57 containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
• CPC Class Codes: C07C 259/06 having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
• CPC Class Codes: C07C 2601/02 with a three-membered ring
• CPC Class Codes: C07C 2601/04 with a four-membered ring
• CPC Class Codes: C07C 271/08 : having oxygen atoms of carbamate groups bound to acyclic carbon atoms
• CPC Class Codes: C07C 281/02 : Compounds containing any of the groups , e.g. carbazates
• CPC Class Codes: C07C 327/42 : to hydrogen atoms or to carbon atoms of a saturated carbon skeleton
• CPC Class Codes: C07C 327/46 : having carbon atoms of thiocarboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
• CPC Class Codes: C07C 327/48 : having carbon atoms of thiocarboxamide groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07D 207/273 : with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
• CPC Class Codes: C07D 211/56 : Nitrogen atoms nitro radicals C07D211/38
• CPC Class Codes: C07D 261/04 : having one double bond between ring members or between a ring member and a non-ring member

Abstract

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”).

Claims

1. A molecule having the following formula

2. A molecule according to claim 1 wherein R¹, R³, R⁴, R⁵, R⁶, R⁹, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, and R¹⁷ are H.

3. A molecule according to claim 1 wherein R² is F, Cl, Br, or CH₃.

4. A molecule according to claim 1 wherein R³ is F, Cl, Br, or CH═

CH₂.

5. A molecule according to claim 1 wherein R⁴ is Cl, Br, or CH₃.

6. A molecule according to claim 1 wherein R², R³, and R⁴ are C₁.

7. A molecule according to claim 1 wherein R⁷ is (C₁-C₆)haloalkyl.

8. A molecule according to claim 1 wherein R⁷ is CF₃, CF₂CH₃, or CF₂CH₂CH₃.

9. A molecule according to claim 1 wherein R¹⁰ is Cl, Br, I, CH₃, or CF₃.

10. A molecule according to claim 1 wherein Q¹ and Q² are O.

11. A molecule according to claim 1 wherein R¹³, R¹⁴, and R¹⁵ are CH₃ or CH₂CH₃.

12. A molecule according to claim 1 wherein R¹⁴ and R¹⁵ together form a 2-membered saturated, hydrocarbyl link.

13. A molecule according to claim 1 wherein L is a bond connecting C(R¹⁴)(R¹⁵) to C(=Q²).

14. A molecule according to claim 1 wherein X is a bond connecting C(=Q²) to R¹⁷.

15. A molecule according to claim 1 wherein X is N connecting C(=Q²) to R¹⁷.

16. A molecule according to claim 1 wherein R¹⁶ is CH₃, CH₂CH₃, OCH₃, OCH₂CH═

CH₂, NH₂, or NHC(O)OC(CH₃)₃.

17. A molecule according to claim 1 wherein R¹⁴ and R¹⁶ together form a 2- to 4-membered saturated, hydrocarbyl link, which may contain one or more oxygen heteroatoms.

18. A molecule according to claim 1 wherein R¹⁷ is CH₂CH₃, CH₂CH₂CH₂CH₃, CH₂CH₂CH(CH₃)₂, CH₂CH═

CH₂, CH₂C≡

CH, CH₂CHF₂, CH₂CF₃, CH₂CH₂CF₃, CH₂CF₂CH₃, CH(CH₃)CF₃, CH₂CH₂CH₂CF₃, CH═

CHCH₂CF₃, 3,3-difluorocyclobutyl, CH₂CH₂cyclopropyl, and CH₂cyclobutyl.

19. A molecule according to claim 1 wherein

(A) R¹, R⁵, R⁶, R¹¹, and R¹² are H;

(B) R², R³, and R⁴ are each independently selected from the group consisting of H, F, Cl, Br, (C₁-C₆)alkyl, and (C₂-C₆)alkenyl;

(C) R⁷ is (C₁-C₆)haloalkyl;

(D) R⁹ is H;

(E) R¹⁰ is selected from the group consisting of Cl, Br, I, (C₁-C₆)alkyl, and (C₁-C₆)haloalkyl;

(G) Q¹ and Q² are O;

(H) R¹³ is selected from the group consisting of H and (C₁-C₆)alkyl;

(I) R¹⁴ is selected from the group consisting of (K), (O), H, and (C₁-C₄)alkyl;

(J) R¹⁵ is selected from the group consisting of (K), H, and (C₁-C₆)alkyl;

(K) R¹⁴ and R¹⁵ together can optionally form a 2- to 5-membered saturated, hydrocarbyl link;

(L) L is a bond connecting C(R¹⁴)(R¹⁵) to C=Q²;

(M) X is selected from the group consisting of

(1) a bond connecting C(=Q²) to R¹⁷, and

(2) a N, O, and S connecting C(=Q²) to R¹⁷;

(N) R¹⁶ is selected from the group consisting of (O), H, (C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₂-C₆)alkenyloxy, amino, and NHC(O)O(C₁-C₆)alkyl;

(O) R¹⁴ and R¹⁶ together can optionally form a 2- to 4-membered saturated, hydrocarbyl link, which may contain one or more oxygen heteroatoms;

(P) R¹⁷ is selected from the group consisting of H, (C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₁-C₆)haloalkyl, (C₁-C₆)haloalkenyl, (C₃-C₆)halocycloalkyl, and (C₁-C₆)alkyl(C₃-C₆)cycloalkyl.

20. A pesticidal composition comprising a molecule according to claim 1 further comprising one or more active ingredients.

21. A pesticidal composition according to claim 20 wherein said active ingredient is from AIGA.

22. A pesticidal composition comprising a molecule according to claim 1 further comprising one or more MoA Materials.

23. A pesticidal composition according to claim 22 wherein said MoA Material is from MoAMGA.

24. A pesticidal composition comprising a molecule according to claim 1 and a seed.

25. A process to control a pest said process comprising applying to a locus, a pesticidally effective amount of a pesticidal composition wherein said pesticidal composition comprises a molecule according to claim 1.

26. A molecule according to claim 1 wherein said molecule is selected from one of the following molecules

27. A molecule according to claim 1 wherein said molecule is selected from one of the following molecules

28. A pesticidal composition according to claim 20 wherein said active ingredient is selected from the group consisting of chlorpyrifos, chlorpyrifos-methyl, methoxyfenozide, spinetoram, spinosad, and sulfoxaflor.