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

Patent metadata

Field	Value
Publication number	US-9781935-B2
Application number	US-201615092650-A
Country	US
Kind code	B2
Filing date	Apr 7, 2016
Priority date	Apr 17, 2015
Publication date	Oct 10, 2017
Grant date	Oct 10, 2017

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”).

First claim

The invention claimed is:

1. A molecule having the following formula

wherein:
(A) R 1 is selected from the group consisting of H, F, Cl, Br, and I;
(B) R 2 is selected from the group consisting of H, F, Cl, Br, and I;
(C) R 3 is selected from the group consisting of H, F, Cl, Br, and I;
(D) R 4 is selected from the group consisting of H, F, Cl, Br, and I;
(E) R 5 is selected from the group consisting of H, F, Cl, Br, and I;
(F) R 6 is selected from the group consisting of H and (C 1 -C 6 )alkyl;
(G) R 7 is selected from the group consisting of H, F, Cl, Br, and I;
(H) R 8 is selected from the group consisting of F, Cl, Br, and I;
(I) R 9 is selected from the group consisting of H and (C 1 -C 6 )alkyl;
(J) Q 1 is O;
(K) Q 2 is O;
(L) R 10 is selected from the group consisting of H, and (C 1 -C 6 )alkyl;
(M) R 11 is selected from the group consisting of H, F, Cl, Br, and I;
(N) R 12 is selected from the group consisting of H, F, Cl, Br, and I;
(O) X 1 is CR 13 ,
wherein R 13 is (C 1 -C 6 )alkyl;

(P) X 2 is CR 14 ,
wherein R 14 is

(Q) X 3 is selected from the group consisting of N(R 15 ) (substituted or unsubstituted phenyl), N(R 15 ) (substituted or unsubstituted heterocyclyl), and substituted or unsubstituted heterocyclyl,
(a) wherein said R 15 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 )alkyl(C 1 -C 6 )alkoxy, C(═O)(C 1 -C 6 )alkyl, and (C 1 -C 6 )alkoxyC(═O)(C 1 -C 6 )alkyl,
(b) wherein said substituted phenyl and substituted heterocyclyl has one or more substituents selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO 2 , OH, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkylphenyl, (C 1 -C 6 )alkyl-S(O) 2 NH 2 , (C 1 -C 6 )haloalkoxy, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )haloalkyl-S(O) 2 NH 2 , (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 2 -C 6 )haloalkenyl, (C 3 -C 6 )cycloalkenyl, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )halocycloalkenyl, (C 3 -C 6 )halocycloalkyl, (C 1 -C 6 )alkyl((C 1 -C 6 )alkyl)(═NO(C 1 -C 6 )alkyl), C(═NO(C 1 -C 6 )alkyl)(C 1 -C 6 )alkyl, C(O)(C 1 -C 6 )alkyl, C(O)NH(C 1 -C 6 )alkyl, C(O)NHphenyl, C(O)O(C 1 -C 6 )alkyl, CH(═NO(C 1 -C 6 )alkyl), imidazolyl, N((C 1 -C 6 )alkyl)(C(O)(C 1 -C 6 )alkyl), N((C 1 -C 6 )alkyl)(C(O)(C 1 -C 6 )alkyl-O(C 1 -C 6 )alkyl), N((C 1 -C 6 )alkyl)(C(O)(C 1 -C 6 )haloalkyl), N((C 1 -C 6 )alkyl)(C(O)O(C 1 -C 6 )alkyl), N((C 1 -C 6 )alkyl) 2 , N(C(O)O(C 1 -C 6 )alkyl) 2 , N═CH-phenyl, NH((C 1 -C 6 )alkylC(O)(C 1 -C 6 )alkyl), NH(C(O)(C 1 -C 6 )alkyl), NH(C(O)(C 2 -C 6 )alkenyl), NH(C(O)(C 3 -C 6 )cycloalkyl), NH(C 1 -C 6 )alkyl, NH(C 1 -C 6 )alkenyl, NH(C 1 -C 6 )alkynyl, NH(C 1 -C 6 )alkylphenyl, NH(S(O) 2 (C 1 -C 6 )alkyl), NH 2 , NHC(O)(C 1 -C 6 )alkyl, NHC(O)(C 1 -C 6 )alkylphenyl, NHC(O)(C 1 -C 6 )alkylphenyl, NHC(O)(C 1 -C 6 )haloalkyl, NHC(O)(C 2 -C 6 )alkenyl, NH—C(O)O(C 1 -C 6 )alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C 1 -C 6 )alkyl), S(C 1 -C 6 )alkyl, S(C 1 -C 6 )haloalkyl, S(O)(═NCN)((C 1 -C 6 )alkyl), S(O)(C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )haloalkyl, S(O) 2 (C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C 1 -C 6 )alkyl, NH(C 3 -C 6 )cycloalkylCH 2 O(C 1 -C 6 )alkyl, NH(C 3 -C 6 )cycloalkylCH 2 O(C 1 -C 6 )haloalkyl, NHCH 2 (C 3 -C 6 )cycloalkyl, NH 2 , NO 2 , oxo, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, and C(O)O—(C 1 -C 6 )alkyl; and

N-oxides, agriculturally acceptable acid addition salts, solvates, isotopes, resolved stereoisomers, and tautomers, of the molecules of Formula One.

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 R 1 is selected from the group consisting of H, F, or Cl.

4. The molecule according to claim 1 wherein R 2 is selected from the group consisting of H, F, Cl, and Br.

5. The molecule according to claim 1 wherein R 3 is selected from the group consisting of H, F, Cl, and Br.

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

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

8. The molecule according to claim 1 wherein R 6 is H.

9. The molecule according to claim 1 wherein R 7 is selected from the group consisting of Cl and Br.

10. The molecule according to claim 1 wherein R 8 is selected from the group consisting of Cl and Br.

11. The molecule according to claim 1 wherein R 9 is H.

12. The molecule according to claim 1 wherein R 10 is selected from the group consisting of H and CH 3 .

13. The molecule according to claim 1 wherein R 11 is selected from the group consisting of H, F, and Cl.

14. The molecule according to claim 1 wherein R 12 is selected from the group consisting of H and Cl.

15. The molecule according to claim 1 wherein R 13 is selected from the group consisting of CH 3 .

16. The molecule according to claim 1 wherein R 14 is H.

17. The molecule according to claim 1 wherein X 3 is selected from the group consisting of

(a) R 15 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 )alkyl(C 1 -C 6 )alkoxy, C(═O)(C 1 -C 6 )alkyl, and (C 1 -C 6 )alkoxyC(═O)(C 1 -C 6 )alkyl;
(b) X 4 is selected from the group consisting of
(i) N,

(ii) NO, and
(iii) CR 16 ,
wherein R 16 is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , CHO, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 6 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 6 )haloalkoxy, S(C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )alkyl, S(C 1 -C 6 )haloalkyl, S(O)(C 1 -C 6 )haloalkyl, S(O) 2 (C 1 -C 6 )haloalkyl, CO(C 1 -C 6 )alkyl, CH(═NO(C 1 -C 6 )alkyl), C(═NO(C 1 -C 6 )alkyl)(C 1 -C 6 )alkyl, (C 1 -C 6 )alkyl-S(O) 2 NH 2 , and (C 1 -C 6 )haloalkyl-S(O) 2 NH 2 ,
wherein each alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, haloalkyl, halocycloalkyl, haloalkenyl, halocycloalkenyl, and haloalkoxy, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH 2 , NO 2 , oxo, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, and C(O)O—(C 1 -C 6 )alkyl;

(c) X 5 is selected from the group consisting of
(i) N,

(ii) NO, and
(iii) CR 17 ,
wherein R 7 is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 6 )haloalkenyl, (C 3 -C

Assignees

• Dow Agrosciences Llc

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

Classifications

• C07C311/08

  having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring · CPC title

• C07D207/273

  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 title

• C07D215/38

  Nitrogen atoms (nitro radicals C07D215/18) · CPC title

• C07C255/29

  containing cyano groups and acylated amino groups bound to the carbon skeleton · CPC title

• C07D233/36

  with hydrocarbon radicals, substituted by nitrogen atoms, attached to ring nitrogen atoms · CPC title