IP Library › Granted Patent US 9,781,935

Granted Patent B2

US 9,781,935 · App. 15/092,650 · Granted Oct 10, 2017

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

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Patent No.: US 9,781,935
App. No.: 15/092,650
Granted: Oct 10, 2017
Kind: B2

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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 (230)

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;

(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;

(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 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, C(O)O(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 ;

(d) X° is selected from the group consisting of

(i) N,

(ii) NO, and

(iii) and CR 18 ,

wherein R 18 is selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , OH, NH 2 , SCN, CHO, (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, (C 1 -C 6 )haloalkoxy, NH(C 1 -C 6 )alkyl, N((C 1 -C 6 )alkyl) 2 , 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, CONH(C 1 -C 6 )alkyl, NHCO(C 1 -C 6 )alkyl, N(C 1 -C 6 )alkyl-CO(C 1 -C 6 )alkyl, NHCO(C 2 -C 6 )alkenyl, NHCO(C 3 -C 6 )cycloalkyl, NHCO(C 1 -C 6 )haloalkyl, N(C 1 -C 6 )alkyl-CO(C 1 -C 6 )haloalkyl, NHCO(C 1 -C 6 )alkylphenyl, NH—C(O)O(C 1 -C 6 )alkyl, N(C 1 -C 6 )alkyl-C(O)O(C 1 -C 6 )alkyl, CH(═NO(C 1 -C 6 )alkyl), C(═NO(C 1 -C 6 )alkyl)(C 1 -C 6 )alkyl, phenyl, pyrazolyl, imidazolyl, and triazolyl,

wherein each alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, haloalkoxy, halocycloalkyl, cycloalkyl, phenyl, imidazolyl, and triazolyl, 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;

(e) X 7 is selected from the group consisting of

(i) N,

(ii) NO, and

(iii) CR 19 ,

wherein R 19 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 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, C(O)O(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 ;

(f) X 8 is selected from the group consisting of

(i) N,

(ii) NO, and

(iii) CR 20 ,

wherein R 20 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 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, C(O)O(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 ;

(g) R 21 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 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, (C 1 -C 6 )alkyl-S(O) 2 NH 2 , (C 1 -C 6 )haloalkyl-S(O) 2 NH 2 , phenyl, pyridinyl, and thienyl,

wherein each alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, haloalkoxy, phenyl, imidazolyl, and triazolyl, 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,

(h) R 2 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 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, (C 1 -C 6 )alkyl-S(O) 2 NH 2 , (C 1 -C 6 )haloalkyl-S(O) 2 NH 2 , phenyl, pyridinyl, and thienyl,

wherein each alkyl, alkenyl, alkynyl, haloalkyl, alkoxy,

haloalkoxy, phenyl, imidazolyl, and triazolyl, 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 2 -C 6 )alkyl,

(i) R 23 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 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, (C 1 -C 6 )alkyl-S(O) 2 NH 2 , (C 1 -C 6 )haloalkyl-S(O) 2 NH 2 , phenyl, pyridinyl, and thienyl,

(j) R 24 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 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, (C 1 -C 6 )alkyl-S(O) 2 NH 2 , (C 1 -C 6 )haloalkyl-S(O) 2 NH 2 , phenyl, pyridinyl, and thienyl,

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

19. The molecule according to claim 1 wherein X 3 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, NH 2 , NO 2 , (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkoxy, (C 1 -C 6 )haloalkyl, (C 2 -C 6 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, and (C 3 -C 6 )halocycloalkyl.

20. The molecule according to claim 1 wherein X 3 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, NO 2 , NH 2 , (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkoxy, (C 1 -C 6 )haloalkyl, (C 2 -C 6 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, and (C 3 -C 6 )halocycloalkyl.

21. The molecule according to claim 1 , wherein X 3 is N(R 15 ) (substituted or unsubstituted phenyl),

(a) wherein said R 15 is selected from the group consisting of H, and (C 1 -C 6 )alkyl,

(b) wherein said substituted phenyl has one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NO 2 , NH 2 , (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkoxy, (C 1 -C 6 )haloalkyl, (C 2 -C 6 )haloalkenyl, (C 3 -C 6 )cycloalkenyl, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )halocycloalkenyl, and (C 3 -C e )halocycloalkyl.

22. The molecule according to claim 1 wherein R 15 is selected from the group consisting of H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH 2 CH═CH 2 , CH 2 —C≡CH, and CH 2 CF 3 .

23. The molecule according to claim 17 wherein X 4 is selected from the group consisting of N and CR 16 .

24. The molecule according to claim 17 wherein R 16 is selected from the group consisting of H, F, Cl, CN, NH 2 , CH 3 , CH 2 CH 3 , and CH 2 (CH 3 ) 2 .

25. The molecule according to claim 17 wherein X 5 is selected from the group consisting of N and CR 17 .

26. The molecule according to claim 17 wherein R 17 is selected from the group consisting of H, F, Cl, CN, and NH 2 .

27. The molecule according to claim 17 wherein X 6 is selected from the group consisting of N and CR 18 .

28. The molecule according to claim 17 wherein R 18 is selected from the group consisting of H, F, Cl, CN, NO 2 , NH 2 , CH 3 , CF 3 , OCH 3 , OCHCF 2 , OCF 3 , SCH 3 , S(O)CH 3 , S(O) 2 CH 3 , C(O)NHCH 3 , and NHC(O)CH 3 .

29. The molecule according to claim 17 wherein X 7 is CR 19 .

30. The molecule according to claim 17 wherein R 19 is selected from the group consisting of H, F, and NH 2 .

31. The molecule according to claim 17 wherein X 8 is CR 20 .

32. The molecule according to claim 17 wherein R 20 is selected from the group consisting of H, F, Cl, and CH 3 .

33. The molecule according to claim 17 wherein R 21 is H.

34. The molecule according to claim 17 wherein R 22 is H.

35. The molecule according to claim 17 wherein R 23 is H.

36. The molecule according to claim 17 wherein R 24 is H.

37. The molecule according to claim 1 wherein

(A) R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , and R 12 are each independently selected from the group consisting of H, F, Cl, Br;

(B) R 6 and R 9 are H;

(D) R 8 is selected from the group consisting of Cl and Br;

(E) Q 1 and Q 2 are O;

(F) R 10 is H;

(G) X 1 is

wherein R 13 is (C 1 -C 6 )alkyl;

(H) X 2 is CR 14 selected from the group consisting of

wherein R 14 is H;

(I) X 3 is selected from the group consisting of

wherein:

(a) R 15 is selected from the group consisting of H, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, and (C 1 -C 6 )haloalkyl;

(b) X 4 is selected from the group consisting of

(i) N, and

(ii) CR 16 ,

wherein R 16 is selected from the group consisting of H, F, Cl, CN, NH 2 , and (C 1 -C 6 )alkyl;

(i) N,

(ii) NO, and

(iii) CR 17 ,

wherein R 17 is selected from the group consisting of H, F, Cl, NH 2 , and CN;

(d) X 6 is selected from the group consisting of

(i) N,

(ii) NO, and

(iii) and CR 18 ,

wherein R 18 is selected from the group consisting of H, F, Cl, CN, NO 2 , NH 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (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, CONH(C 1 -C 6 )alkyl, and NHCO(C 1 -C 6 )alkyl;

(e) X 7 is CR 19 ,

wherein R 19 is selected from the group consisting of H, NH 2 , and F;

(f) X 8 is CR 20 ,

wherein R 20 is selected from the group consisting of H, F, Cl, NH 2 , and (C 1 -C 6 )alkyl; and

(g) R 21 , R 22 , R 23 , and R 24 are H.

38. The molecule according to claim 1 wherein

(A) R 1 is H;

(B) R 2 is selected from the group consisting of H, Cl, and Br;

(D) R 4 is selected from the group consisting of H, Cl, and Br;

(E) R 5 is selected from the group consisting of H and Cl;

(F) R 6 is H;

(G) R 7 is selected from the group consisting of Cl and Br;

(H) R 8 is selected from the group consisting of Cl and Br;

(I) R 9 is H;

(J) Q 1 is O;

(K) Q 2 is O;

(L) R 10 is H;

(M) R 11 is selected from the group consisting of H, F, and Cl;

(N) R 12 is selected from the group consisting of H and Cl;

(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 H; and

(Q) X 3 is selected from the group consisting of

wherein:

(a) R 15 is selected from the group consisting of H, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, and (C 1 -C 6 )haloalkyl;

(b) X 4 is selected from the group consisting of

(i) N, and

(ii) CR 16 ,

wherein R 16 is selected from the group consisting of H, F, Cl, CN, NH 2 , and (C 1 -C 6 )alkyl;

(i) N,

(ii) NO, and

(iii) CR 17 ,

wherein R 17 is selected from the group consisting of H, F, Cl, NH 2 , and CN;

(d) X 6 is selected from the group consisting of

(i) N,

(ii) NO, and

(iii) and CR 18 ,

(e) X 7 is CR 19 ,

wherein R 19 is selected from the group consisting of H, NH 2 , and F;

(f) X 8 is CR 20 ,

wherein R 20 is selected from the group consisting of H, F, Cl, NH 2 , and (C 1 -C 6 )alkyl; and

(g) R 21 , R 22 , R 23 , and R 24 are H.

39. The molecule according to claim 1 wherein:

(A) R 1 is selected from the group consisting of H, F, and Cl;

(B) R 2 is selected from the group consisting of H, F, Cl, and Br;

(D) R 4 is selected from the group consisting of H, F, Cl, and Br;

(E) R 5 is selected from the group consisting of H, F, and Cl;

(F) R 6 is H;

(G) R 7 is selected from the group consisting of Cl and Br;

(H) R 8 is selected from the group consisting of Cl and Br;

(I) R 9 is H;

(J) Q 1 is O;

(K) Q 2 is O;

(L) R 10 is H;

(M) R 11 is selected from the group consisting of H, F, and Cl;

(N) R 12 is selected from the group consisting of H and Cl;

(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 H; and

(Q) X 3 is

wherein:

R 15 is selected from the group consisting of H, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, and (C 1 -C 6 )haloalkyl;

X 4 is CR 16 wherein R 16 is selected from the group consisting of H, F, Cl, NH 2 , CN, NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )haloalkoxy;

X 5 is CR 17 wherein R 7 is selected from the group consisting of H, F, Cl, NH 2 , CN, NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )haloalkoxy;

X 6 is CR 18 wherein R 18 is selected from the group consisting of H, F, Cl, NH 2 , CN, NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )haloalkoxy;

X 7 is CR 19 wherein R 19 is selected from the group consisting of H, F, Cl, NH 2 , CN, NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )haloalkoxy;

X 8 is CR 20 wherein R 20 is selected from the group consisting of H, F, Cl, CN, NH 2 , NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )haloalkoxy.

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

No.

Structure

F14

F18

F19

F22

F24

F25

F28

F31

F35

F37

F38

F39

F44

F51

F52

F53

F55

F77

F129

F279

PF5

PF35

PF38

Assignments (2)

CHANGE OF NAME Recorded Nov 8, 2021

From: DOW AGROSCIENCES LLC

To: CORTEVA AGRISCIENCE LLC

Reel/Frame 058044/0184 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 8, 2016

From: HEEMSTRA, RONALD J.; ROSS, RONALD, JR.; DEKORVER, KYLE; GRAY, KAITLYN; KNUEPPEL, DANIEL I.; VEDNOR, PETER; MARTIN, TIMOTHY P.; ECKELBARGER, JOSEPH D.; DAEUBLE, JOHN F., SR.; 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.

To: DOW AGROSCIENCES LLC

Reel/Frame 038389/0332 →