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

• US 9,924,717 B2
• Filed: 01/18/2017
• Issued: 03/27/2018
• 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., Lawler, Lori K., Lo, William C., Petkus, Jeff, Boruwa, Joshodeep, Tangirala, Raghuram, Watson, Gerald B., Herbert, John
• Primary Examiner(s): Otton, Alicia L
• Assistant Examiner(s): Chen, Po-Chih
• Application Number:
  US15/408,634
• Publication Number:
  US 20170208805A1
• Time in Patent Office: 433 Days
• Field of Search: None
• CPC Class Codes: A01N 29/12 1,1-Di- or 1,1,1-trihalo-2-aryl-ethane or -ethene or derivatives thereof, e.g. DDT
• CPC Class Codes: A01N 31/04 Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
• CPC Class Codes: A01N 33/04 Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
• CPC Class Codes: A01N 35/04 containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
• CPC Class Codes: A01N 37/10 Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
• 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 37/20 containing the group , wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
• CPC Class Codes: A01N 37/26 containing the group; Thio analogues thereof
• CPC Class Codes: A01N 43/20 three- or four-membered rings
• CPC Class Codes: A01N 43/36 five-membered rings
• CPC Class Codes: A01N 43/40 six-membered rings
• 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 233/65 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 233/73 of a carbon skeleton containing six-membered aromatic rings
• CPC Class Codes: C07C 233/78 with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
• CPC Class Codes: C07C 251/28 having nitrogen atoms of imino groups acylated
• CPC Class Codes: C07C 251/38 to carbon atoms of a saturated carbon skeleton
• CPC Class Codes: C07C 255/46 to carbon atoms of non-condensed rings
• CPC Class Codes: C07C 257/20 having nitrogen atoms of amidino groups acylated
• CPC Class Codes: C07C 259/14 : having carbon atoms of hydroxamidine 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 2601/14 : The ring being saturated
• 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 207/06 : with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
• CPC Class Codes: C07D 213/61 : Halogen atoms or nitro radicals
• 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 331/04 : Four-membered rings

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, and R¹⁴ are H.

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

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

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 Cl.

7. A molecule according to claim 1 wherein R⁷ is CF₃.

8. A molecule according to claim 1 wherein R¹⁰ is Br, CH₃, or CF₃.

9. A molecule according to claim 1 wherein R¹³ and R¹⁴ are H, CHO, CH₃, CH₂CF₃, CH(CH₃)CF₃, cyclopropyl, cyclobutyl, cyclohexyl, CH(CH₃)phenyl, CH₂pyridyl, pyridyl, and CH═

NOCH₃, wherein said cyclohexyl and phenyl may optionally be substituted with one or more substituents Independently selected from the group consisting of F, Cl, CH₃, and OCH₃.

10. A molecule according to claim 1 wherein R¹³ or R¹⁴ are CHN(CH₃)₂ connected to the nitrogen by a double bond.

11. A molecule according to claim 1 wherein Q is O.

12. 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, and (C₁-C₄)alkyl;

(C) R⁷ is (C₁-C₆)haloalkyl;

(D) R⁹ is H;

(E) R¹⁰ is selected from the group consisting of Br, (C₁-C₄)alkyl, and (C₁-C₄)haloalkyl;

(G) R¹³ and R¹⁴ are each Independently selected from the group consisting of H, CHO, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₃-C₈)cycloalkyl, (C₁-C₄)alkyl phenyl, (C₁-C₄)alkyl pyridyl, pyridyl, and CH═

NO(C₁-C₄)alkyl,

wherein each alkyl, haloalkyl, cycloalkyl, phenyl, and pyridyl may optionally be substituted with one or more substituents Independently selected from the group consisting of F, Cl, (C₁-C₄)alkyl, and (C₁-C₄)alkoxy;

(H) R¹³ or R¹⁴ can optionally be CHN((C₁-C₄)alkyl)₂ connected the nitrogen by a double bond;

(I) R¹³ and R¹⁴ together can optionally form a 2- to 6-membered saturated, hydrocarbyl link,

wherein said hydrocarbyl link may optionally be substituted with one or more aid substituents Independently selected from the group consisting of F, Cl, Br, I, and CN; and

(J) Q Is selected from the group consisting of O and S.

13. A molecule according to claim 1 wherein said molecule Is selected from one of the following

14. A molecule according to claim 1 wherein said molecule Is selected from one of the following

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

16. A pesticidal composition according to claim 15 wherein said active Ingredient Is from AIGA.

17. A pesticidal composition according to claim 15 wherein said active Ingredient Is selected from the group consisting of 1,3-dichloropropene, chlorpyrifos, chlorpyrifos-methyl, hexaflumuron, methoxyfenozide, noviflumuron, spinetoram, spinosad, sulfoxaflor, and sulfuryl fluoride.

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

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