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

• US 9,781,935 B2
• Filed: 04/07/2016
• Issued: 10/10/2017
• Est. Priority Date: 04/17/2015
• Status: Active Grant

• Current Assignee: Corteva Agriscience LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Heemstra, Ronald J., Ross, Jr., Ronald, DeKorver, Kyle, Gray, Kaitlyn, Knueppel, Daniel I., Vednor, Peter, Martin, Timothy P., Eckelbarger, Joseph D., Daeuble, Sr., John F., Hunter, Ricky, Demeter, David A., Trullinger, Tony K., Baum, Erich, Benko, Zoltan L., Choy, Nakyen, Crouse, Gary, Li, Fangzheng, Nissen, Jeff, Olson, Monica B., Riener, Michelle, Sparks, Thomas C., Wessels, Frank J., Yap, Maurice C.
• Primary Examiner(s): CHU, YONG LIANG
• Application Number:
  US15/092,650
• Publication Number:
  US 20160304522A1
• Time in Patent Office: 551 Days
• Field of Search: None
• CPC Class Codes: A01N 37/22 the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
• CPC Class Codes: A01N 37/34 Nitriles
• CPC Class Codes: A01N 41/10 Sulfones; Sulfoxides
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/60 1,4-Diazines; Hydrogenated 1,4-diazines
• CPC Class Codes: A01N 43/653 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• CPC Class Codes: A01N 43/707 1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
• CPC Class Codes: A01N 43/82 five-membered rings with three ring hetero atoms
• CPC Class Codes: A01N 43/90 having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• 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: C07C 233/63 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 233/65 having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
• CPC Class Codes: C07C 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 237/42 having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
• CPC Class Codes: C07C 255/29 containing cyano groups and acylated amino groups bound to the carbon skeleton
• CPC Class Codes: C07C 255/46 to carbon atoms of non-condensed rings
• 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 255/60 at least one of the singly-bound nitrogen atoms being acylated
• CPC Class Codes: C07C 259/10 having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
• 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 2601/08 : the ring being saturated
• CPC Class Codes: C07C 2601/14 : The ring being saturated
• CPC Class Codes: C07C 271/28 : to a carbon atom of a non-condensed six-membered aromatic ring
• CPC Class Codes: C07C 271/66 : Y being a hetero atom
• CPC Class Codes: C07C 311/08 : having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 311/46 : Y being a hydrogen or a carbon atom
• CPC Class Codes: C07C 317/14 : having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07C 317/28 : with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
• CPC Class Codes: C07C 317/40 : Y being a hydrogen or a carbon atom
• CPC Class Codes: C07C 317/50 : at least one of the nitrogen atoms being part of any of the groups , X being a hetero atom, Y being any atom
• CPC Class Codes: C07C 323/41 : Y being a hydrogen or an acyclic carbon atom
• CPC Class Codes: C07C 323/42 : Y being a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 323/59 : with acylated amino groups bound to the carbon skeleton
• CPC Class Codes: C07C 331/12 : having sulfur atoms of thiocyanate groups bound to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
• CPC Class Codes: C07C 381/10 : Compounds containing sulfur atoms doubly-bound to nitrogen atoms
• CPC Class Codes: C07D 205/04 : having no double bonds between ring members or between ring members and non-ring members
• CPC Class Codes: C07D 207/10 : 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 ring carbon atoms
• 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 207/452 : with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 209/49 : and having in the molecule an acyl radical containing a saturated three-membered ring, e.g. chrysanthemumic acid esters
• CPC Class Codes: C07D 213/56 : Amides
• CPC Class Codes: C07D 213/75 : Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
• CPC Class Codes: C07D 213/81 : Amides; Imides
• CPC Class Codes: C07D 213/84 : Nitriles
• CPC Class Codes: C07D 213/89 : with hetero atoms directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 215/227 : only one oxygen atom which is attached in position 2
• CPC Class Codes: C07D 215/38 : Nitrogen atoms nitro radicals C07D215/18
• CPC Class Codes: C07D 231/12 : with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 231/56 : Benzopyrazoles; Hydrogenated benzopyrazoles
• CPC Class Codes: C07D 233/36 : with hydrocarbon radicals, substituted by nitrogen atoms, attached to ring nitrogen atoms
• CPC Class Codes: C07D 233/80 : with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
• CPC Class Codes: C07D 235/30 : Nitrogen atoms not forming part of a nitro radical
• CPC Class Codes: C07D 241/20 : Nitrogen atoms nitro radicals C07D241/16
• CPC Class Codes: C07D 249/08 : 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• CPC Class Codes: C07D 253/07 : 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 ring carbon atoms
• CPC Class Codes: C07D 261/12 : Oxygen atoms
• CPC Class Codes: C07D 263/26 : with hetero atoms or acyl radicals directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 277/30 : Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• CPC Class Codes: C07D 277/36 : Sulfur atoms
• CPC Class Codes: C07D 285/06 : 1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
• CPC Class Codes: C07D 295/32 : acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues
• CPC Class Codes: C07D 305/08 : 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 ring atoms
• CPC Class Codes: C07D 307/33 : in position 2, the oxygen atom being in its keto or unsubstituted enol form
• CPC Class Codes: C07D 307/52 : Radicals substituted by nitrogen atoms not forming part of a nitro radical
• CPC Class Codes: C07D 309/14 : Nitrogen atoms not forming part of a nitro radical
• CPC Class Codes: C07D 331/04 : Four-membered rings
• CPC Class Codes: C07D 333/36 : Nitrogen atoms
• CPC Class Codes: C07D 333/48 : by oxygen atoms
• CPC Class Codes: C07D 333/60 : Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• CPC Class Codes: C07D 487/04 : Ortho-condensed systems
• CPC Class Codes: Y02A 50/30 : Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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, pesticidal compositions containing such molecules, and processes of using such pesticidal compositions against such pests. These pesticidal 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. The molecule according to claim 1 wherein the carboxamido, and the phenyl, which are bonded to the cyclopropane, are in the R,R configuration.

3. The molecule according to claim 1 wherein R¹ is selected from the group consisting of H, F, or Cl.

4. The molecule according to claim 1 wherein R² is selected from the group consisting of H, F, Cl, and Br.

5. The molecule according to claim 1 wherein R³ is selected from the group consisting of H, F, Cl, and Br.

6. The molecule according to claim 1 wherein R⁴ is selected from the group consisting of H, F, Cl, and Br.

7. The molecule according to claim 1 wherein R⁵ is selected from the group consisting of H, F, and Cl.

8. The molecule according to claim 1 wherein R⁶ is H.

9. The molecule according to claim 1 wherein R⁷ is selected from the group consisting of Cl and Br.

10. The molecule according to claim 1 wherein R⁸ is selected from the group consisting of Cl and Br.

11. The molecule according to claim 1 wherein R⁹ is H.

12. The molecule according to claim 1 wherein R¹⁰ is selected from the group consisting of H and CH₃.

13. The molecule according to claim 1 wherein R¹¹ is selected from the group consisting of H, F, and Cl.

14. The molecule according to claim 1 wherein R¹² is selected from the group consisting of H and Cl.

15. The molecule according to claim 1 wherein R¹³ is selected from the group consisting of CH₃.

16. The molecule according to claim 1 wherein R¹⁴ is H.

17. The molecule according to claim 1 wherein X³ is selected from the group consisting of

18. The molecule according to claim 1 wherein X³ is selected from the group consisting of

19. The molecule according to claim 1 wherein X³ is a substituted or unsubstituted heterocyclyl, wherein said heterocyclyl is selected from the group consisting of Indolyl, oxazolyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridyl, pyrimidinyl, tetrazolyl, thiadiazolyl, thiazolyl, thienyl, triazinyl, [1,2,4]triazolo[1,5-c]pyrimidinyl, triazolyl, 2,3-dihydrophthalazine-1,4-dionyl, Indolinyl, and pyrimidine-2,4(1H,3H)-dionyl,

wherein substituents are selected from the group consisting of F, Cl, Br, I, H, CN, NH₂, NO₂, (C₁-C₆)alkoxy, (C₁-C₆)alkyl, (C₁-C₆)haloalkoxy, (C₁-C₆)haloalkyl, (C₂-C₆)haloalkenyl, (C₃-C₆)halocycloalkenyl, and (C₃-C₆)halocycloalkyl.

20. The molecule according to claim 1 wherein X³ is a substituted or unsubstituted heterocyclyl wherein said heterocyclyl is selected from the group consisting of Indolinyl, oxazolyl, pyridyl, and thiadiazolyl, wherein said substituents are selected from the group consisting of F, Cl, Br, I, H, CN, NO₂, NH₂, (C₁-C₆)alkoxy, (C₁-C₆)alkyl, (C₁-C₆)haloalkoxy, (C₁-C₆)haloalkyl, (C₂-C₆)haloalkenyl, (C₃-C₆)halocycloalkenyl, and (C₃-C₆)halocycloalkyl.

21. The molecule according to claim 1, wherein X³ is N(R¹⁵) (substituted or unsubstituted phenyl),

(a) wherein said R¹⁵ is selected from the group consisting of H, and (C₁-C₆)alkyl,

(b) wherein said substituted phenyl has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO₂, NH₂, (C₁-C₆)alkoxy, (C₁-C₆)alkyl, (C₁-C₆)haloalkoxy, (C₁-C₆)haloalkyl, (C₂-C₆)haloalkenyl, (C₃-C₆)cycloalkenyl, (C₃-C₆)cycloalkyl, (C₃-C₆)halocycloalkenyl, and (C₃-C_e)halocycloalkyl.

22. The molecule according to claim 1 wherein R¹⁵ is selected from the group consisting of H, CH₃, CH₂CH₃, CH₂CH₂CH₃, CH₂CH═

CH₂, CH₂—

C≡

CH, and CH₂CF₃.

23. The molecule according to claim 17 wherein X⁴ is selected from the group consisting of N and CR¹⁶.

24. The molecule according to claim 17 wherein R¹⁶ is selected from the group consisting of H, F, Cl, CN, NH₂, CH₃, CH₂CH₃, and CH₂(CH₃)₂.

25. The molecule according to claim 17 wherein X⁵ is selected from the group consisting of N and CR¹⁷.

26. The molecule according to claim 17 wherein R¹⁷ is selected from the group consisting of H, F, Cl, CN, and NH₂.

27. The molecule according to claim 17 wherein X⁶ is selected from the group consisting of N and CR¹⁸.

28. The molecule according to claim 17 wherein R¹⁸ is selected from the group consisting of H, F, Cl, CN, NO₂, NH₂, CH₃, CF₃, OCH₃, OCHCF₂, OCF₃, SCH₃, S(O)CH₃, S(O)₂CH₃, C(O)NHCH₃, and NHC(O)CH₃.

29. The molecule according to claim 17 wherein X⁷ is CR¹⁹.

30. The molecule according to claim 17 wherein R¹⁹ is selected from the group consisting of H, F, and NH₂.

31. The molecule according to claim 17 wherein X⁸ is CR²⁰.

32. The molecule according to claim 17 wherein R²⁰ is selected from the group consisting of H, F, Cl, and CH₃.

33. The molecule according to claim 17 wherein R²¹ is H.

34. The molecule according to claim 17 wherein R²² is H.

35. The molecule according to claim 17 wherein R²³ is H.

36. The molecule according to claim 17 wherein R²⁴ is H.

37. The molecule according to claim 1 wherein

(A) R¹, R², R³, R⁴, R⁵, R¹¹, and R¹² are each independently selected from the group consisting of H, F, Cl, Br;

(B) R⁶ and R⁹ are H;

(C) R⁷ is selected from the group consisting of Cl and Br;

(D) R⁸ is selected from the group consisting of Cl and Br;

(E) Q¹ and Q² are O;

(F) R¹⁰ is H;

(G) X¹ is

wherein R¹³ is (C₁-C₆)alkyl;

(H) X² is CR¹⁴ selected from the group consisting of

wherein R¹⁴ is H;

(I) X³ is selected from the group consisting of

38. The molecule according to claim 1 wherein

(A) R¹ is H;

(B) R² is selected from the group consisting of H, Cl, and Br;

(C) R³ is selected from the group consisting of H, F, Cl, and Br;

(D) R⁴ is selected from the group consisting of H, Cl, and Br;

(E) R⁵ is selected from the group consisting of H and Cl;

(F) R⁶ is H;

(G) R⁷ is selected from the group consisting of Cl and Br;

(H) R⁸ is selected from the group consisting of Cl and Br;

(I) R⁹ is H;

(J) Q¹ is O;

(K) Q² is O;

(L) R¹⁰ is H;

(M) R¹¹ is selected from the group consisting of H, F, and Cl;

(N) R¹² is selected from the group consisting of H and Cl;

(O) X¹ is CR¹³,

wherein R¹³ is (C₁-C₆)alkyl;

(P) X² is CR¹⁴,

wherein R¹⁴ is H; and

(Q) X³ is selected from the group consisting of

39. The molecule according to claim 1 wherein:

(A) R¹ is selected from the group consisting of H, F, and Cl;

(B) R² is selected from the group consisting of H, F, Cl, and Br;

(C) R³ is selected from the group consisting of H, F, Cl, and Br;

(D) R⁴ is selected from the group consisting of H, F, Cl, and Br;

(E) R⁵ is selected from the group consisting of H, F, and Cl;

(F) R⁶ is H;

(G) R⁷ is selected from the group consisting of Cl and Br;

(H) R⁸ is selected from the group consisting of Cl and Br;

(I) R⁹ is H;

(J) Q¹ is O;

(K) Q² is O;

(L) R¹⁰ is H;

(M) R¹¹ is selected from the group consisting of H, F, and Cl;

(N) R¹² is selected from the group consisting of H and Cl;

(O) X¹ is CR¹³,

wherein R¹³ is (C₁-C₆)alkyl;

(P) X² is CR¹⁴,

wherein R¹⁴ is H; and

(Q) X³ is

40. A composition comprising a molecule according to claim 1 and a carrier.

41. A process to control a pest, said process comprising, applying to a locus, a pesticidally effective amount of a molecule according to claim 1.

42. The molecule according to 1 wherein said molecule is selected from one of the following molecules