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

Patent metadata

Field	Value
Publication number	US-10251394-B2
Application number	US-201715408604-A
Country	US
Kind code	B2
Filing date	Jan 18, 2017
Priority date	Jan 25, 2016
Publication date	Apr 9, 2019
Grant date	Apr 9, 2019

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”).

First claim

The invention claimed is:

1. A molecule having the following formula

wherein:
(A) R 1 , R 5 , R 6 , R 11 , and R 12 are each independently selected from the group consisting of H, F, Cl, Br, I, CN, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 4 )haloalkoxy;
(B) R 2 , R 3 , and R 4 are each independently selected from the group consisting of H, F, Cl, Br, I, CN, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )haloalkoxy;
(C) R 7 is (C 1 -C 6 )haloalkyl;
(D) R 9 is selected from the group consisting of (F), H, F, Cl, Br, I, CN, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, and (C 1 -C 4 )haloalkoxy;
(E) R 10 is selected from the group consisting of (F), F, Cl, Br, I, CN, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )haloalkoxy;
(F) R 9 and R 10 together can optionally form a 3- to 5-membered saturated or unsaturated, hydrocarbyl link,
wherein said hydrocarbyl link may optionally be substituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, CN, OH, and oxo;
(G) Q 1 and Q 2 are each independently O or S;
(H) R 13 is selected from the group consisting of H, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )haloalkoxy;
(I) R 14 is selected from the group consisting of (K), (O), H, (C 1 -C 4 )alkyl, (C 2 -C 6 )alkenyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )haloalkoxy;
(J) R 15 is selected from the group consisting of (K), H, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )haloalkoxy;
(K) R 14 and R 15 together can optionally form a 2- to 5-membered saturated, hydrocarbyl link,
wherein said hydrocarbyl link may optionally be substituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, and CN;
(L) L is selected from the group consisting of
(1) a bond connecting C(R 14 )(R 15 ) to C(=Q 2 ), and
(2) a (C 1 -C 6 )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;

(M) X is selected from the group consisting of
(1) a bond connecting C(=Q 2 ) to R 17 , and
(2) a N, O, and S connecting C(=Q 2 ) to R 17 ;

(N) R 16 is selected from the group consisting of (O), H, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 2 -C 6 )alkenyloxy, (C 1 -C 6 )haloalkoxy, amino, and NHC(O)O(C 1 -C 6 )alkyl;
(O) R 14 and R 16 together can optionally form a 2- to 4-membered saturated, hydrocarbyl link, which may contain one or more heteroatoms selected from the group consisting of nitrogen, sulfur, and oxygen,
wherein said hydrocarbyl link may optionally be substituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, CN, OH, and oxo;

(P) R 17 is selected from the group consisting of H, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )haloalkyl, (C 2 -C 6 )haloalkenyl, (C 3 -C 6 )halocycloalkyl, (C 1 -C 6 )alkoxy, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyloxy, (C 1 -C 6 )haloalkoxy, and (C 1 -C 6 )alkyl(C 3 -C 6 )cycloalkyl;
(Q) R 16 and R 17 together can optionally form a 2- to 6-membered saturated, hydrocarbyl link, which may contain one or more heteroatoms selected from the group consisting of nitrogen, sulfur, and oxygen,
wherein said hydrocarbyl link may optionally be substituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, CN, OH, and oxo; 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 R 1 , R 3 , R 4 , R 5 , R 6 , R 9 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , and R 17 are H.

3. A molecule according to claim 1 wherein R 2 is F, Cl, Br, or CH 3 .

4. A molecule according to claim 1 wherein R 3 is F, Cl, Br, or CH═CH 2 .

5. A molecule according to claim 1 wherein R 4 is Cl, Br, or CH 3 .

6. A molecule according to claim 1 wherein R 2 , R 3 , and R 4 are C 1 .

7. A molecule according to claim 1 wherein R 7 is (C 1 -C 6 )haloalkyl.

8. A molecule according to claim 1 wherein R 7 is CF 3 , CF 2 CH 3 , or CF 2 CH 2 CH 3 .

9. A molecule according to claim 1 wherein R 10 is Cl, Br, I, CH 3 , or CF 3 .

10. A molecule according to claim 1 wherein Q 1 and Q 2 are O.

11. A molecule according to claim 1 wherein R 13 , R 14 , and R 15 are CH 3 or CH 2 CH 3 .

12. A molecule according to claim 1 wherein R 14 and R 15 together form a 2-membered saturated, hydrocarbyl link.

13. A molecule according to claim 1 wherein L is a bond connecting C(R 14 )(R 15 ) to C(=Q 2 ).

14. A molecule according to claim 1 wherein X is a bond connecting C(=Q 2 ) to R 17 .

15. A molecule according to claim 1 wherein X is N connecting C(=Q 2 ) to R 17 .

16. A molecule according to claim 1 wherein R 16 is CH 3 , CH 2 CH 3 , OCH 3 , OCH 2 CH═CH 2 , NH 2 , or NHC(O)OC(CH 3 ) 3 .

17. A molecule according to claim 1 wherein R 14 and R 16 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 R 17 is CH 2 CH 3 , CH 2 CH 2 CH 2 CH 3 , CH 2 CH 2 CH(CH 3 ) 2 , CH 2 CH═CH 2 , CH 2 C≡CH, CH 2 CHF 2 , CH 2 CF 3 , CH 2 CH 2 CF 3 , CH 2 CF 2 CH 3 , CH(CH 3 )CF 3 , CH 2 CH 2 CH 2 CF 3 , CH═CHCH 2 CF 3 , 3,3-difluorocyclobutyl, CH 2 CH 2 cyclopropyl, and CH 2 cyclobutyl.

19. A molecule according to claim 1 wherein
(A) R 1 , R 5 , R 6 , R 11 , and R 12 are H;
(B) R 2 , R 3 , and R 4 are each independently selected from the group consisting of H, F, Cl, Br, (C 1 -C 6 )alkyl, and (C 2 -C 6 )alkenyl;
(C) R 7 is (C 1 -C 6 )haloalkyl;
(D) R 9 is H;
(E) R 10 is selected from the group consisting of Cl, Br, I, (C 1 -C 6 )alkyl, and (C 1 -C 6 )haloalkyl;
(G) Q 1 and Q 2 are O;
(H) R 13 is selected from the group consisting of H and (C 1 -C 6 )alkyl;
(I) R 14 is selected from the group consisting of (K), (O), H, and (C 1 -C 4 )alkyl;
(J) R 15 is selected from the group consisting of (K), H, and (C 1 -C 6 )alkyl;
(K) R 14 and R 15 together can optionally form a 2- to 5-membered saturated, hydrocarbyl link;
(L) L is a bond connecting C(R 14 )(R 15 ) to C=Q 2 ;
(M) X is selected from the group consisting of
(1) a bond connecting C(=Q 2 ) to R 17 , and
(2) a N, O, and S connecting C(=Q 2 ) to R 17 ;

(N) R 16 is selected from the group consisting of (O), H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 2 -C 6 )alkenyloxy, amino, and NHC(O)O(C 1 -C 6 )alkyl;
(O) R 14 and R 16 together can optionally form a 2- to 4-membered saturated, hydrocarbyl link, which may contain one or more oxygen heteroatoms;
(P) R 17 is selected from the group consisting of H, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )haloalkenyl, (C 3 -C 6 )halocycloalkyl, and (C 1 -C 6 )alkyl(C 3 -C 6 )cycloalkyl.

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

21. A p

Assignees

• Dow Agrosciences Llc

Inventors

• Barton Thomas
• Gao Xin
• Hunter Jim
• Leplae Jr Paul R
• Lo William C
• Boruwa Joshodeep
• Tangirala Raghuram
• Watson Gerald B
• Herbert John

Classifications

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• C07C255/57

  containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton · CPC title

• C07C327/42

  to hydrogen atoms or to carbon atoms of a saturated carbon skeleton · CPC title

• A01N37/34

  Nitriles · CPC title

• C07C281/02

  Compounds containing any of the groups [IMAGE cpc-sch-C07C-0972.gif], e.g. carbazates · CPC title