IP Library › Granted Patent US 9,795,139
Granted Patent B2
US 9,795,139 · App. 15/092,641 · Granted Oct 24, 2017

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

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Quick Facts
Patent No.
US 9,795,139
App. No.
15/092,641
Granted
Oct 24, 2017
Kind
B2
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 (198)

1. A molecule having the following formula

wherein:

(A) R 1 is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 4 )haloalkoxy, S(C 1 -C 4 )alkyl, S(O)(C 1 -C 4 )alkyl, S(O) 2 (C 1 -C 4 )alkyl, S(C 1 -C 4 )haloalkyl, S(O)(C 1 -C 4 )haloalkyl, S(O) 2 (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl-S(O) 2 NH 2 , and (C 1 -C 4 )haloalkyl-S(O) 2 NH 2 ;

(B) R 2 is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 4 )haloalkoxy, S(C 1 -C 4 )alkyl, S(O)(C 1 -C 4 )alkyl, S(O) 2 (C 1 -C 4 )alkyl, S(C 1 -C 4 )haloalkyl, S(O)(C 1 -C 4 )haloalkyl, S(O) 2 (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl-S(O) 2 NH 2 , and (C 1 -C 4 )haloalkyl-S(O) 2 NH 2 ;

(C) R 3 is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 4 )haloalkoxy, S(C 1 -C 4 )alkyl, S(O)(C 1 -C 4 )alkyl, S(O) 2 (C 1 -C 4 )alkyl, S(C 1 -C 4 )haloalkyl, S(O)(C 1 -C 4 )haloalkyl, S(O) 2 (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl-S(O) 2 NH 2 , and (C 1 -C 4 )haloalkyl-S(O) 2 NH 2 ;

(D) R 4 is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 4 )haloalkoxy, S(C 1 -C 4 )alkyl, S(O)(C 1 -C 4 )alkyl, S(O) 2 (C 1 -C 4 )alkyl, S(C 1 -C 4 )haloalkyl, S(O)(C 1 -C 4 )haloalkyl, S(O) 2 (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl-S(O) 2 NH 2 , and (C 1 -C 4 )haloalkyl-S(O) 2 NH 2 ;

(E) R 5 is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 4 )haloalkoxy, S(C 1 -C 4 )alkyl, S(O)(C 1 -C 4 )alkyl, S(O) 2 (C 1 -C 4 )alkyl, S(C 1 -C 4 )haloalkyl, S(O)(C 1 -C 4 )haloalkyl, S(O) 2 (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl-S(O) 2 NH 2 , and (C 1 -C 4 )haloalkyl-S(O) 2 NH 2 ;

(F) R 6 is selected from the group consisting of H and (C 1 -C 4 )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 4 )alkyl;

(J) R 10 is selected from the group consisting of H, (C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl(C 1 -C 4 )alkoxy, C(═O)(C 1 -C 4 )alkyl, and (C 1 -C 4 )alkoxyC(═O)(C 1 -C 4 )alkyl;

(K) R 11 is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 4 )haloalkoxy, S(C 1 -C 4 )alkyl, S(O)(C 1 -C 4 )alkyl, S(O) 2 (C 1 -C 4 )alkyl, S(C 1 -C 4 )haloalkyl, S(O)(C 1 -C 4 )haloalkyl, S(O) 2 (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl-S(O) 2 NH 2 , and (C 1 -C 4 )haloalkyl-S(O) 2 NH 2 ;

(L) R 12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 4 )haloalkoxy, S(C 1 -C 4 )alkyl, S(O)(C 1 -C 4 )alkyl, S(O) 2 (C 1 -C 4 )alkyl, S(C 1 -C 4 )haloalkyl, S(O)(C 1 -C 4 )haloalkyl, S(O) 2 (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl-S(O) 2 NH 2 , and (C 1 -C 4 )haloalkyl-S(O) 2 NH 2 ;

(M) R 13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 4 )haloalkoxy, S(C 1 -C 4 )alkyl, S(O)(C 1 -C 4 )alkyl, S(O) 2 (C 1 -C 4 )alkyl, S(C 1 -C 4 )haloalkyl, S(O)(C 1 -C 4 )haloalkyl, S(O) 2 (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl-S(O) 2 NH 2 , and (C 1 -C 4 )haloalkyl-S(O) 2 NH 2 ;

(N) R 14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 4 )haloalkoxy, S(C 1 -C 4 )alkyl, S(O)(C 1 -C 4 )alkyl, S(O) 2 (C 1 -C 4 )alkyl, S(C 1 -C 4 )haloalkyl, S(O)(C 1 -C 4 )haloalkyl, S(O) 2 (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl-S(O) 2 NH 2 , and (C 1 -C 4 )haloalkyl-S(O) 2 NH 2 ;

(O) R 15 is selected from the group consisting of H, (C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl(C 1 -C 4 )alkoxy, C(═O)(C 1 -C 4 )alkyl, and (C 1 -C 4 )alkoxyC(═O)(C 1 -C 4 )alkyl;

(P) R 16 is selected from the group consisting of (C 3 -C 8 )cycloalkyl, azetidinyl, 2,5-dioxoimidazolidinyl, 2,4-dioxo-1,3-diazaspiro[4.4]nonanylisoxazolidinonyl, imidazolidinonyl, isoxazolidinonyl, morpholinyl, oxazolidinonyl, oxetanyl, piperazinyl, piperidinyl, pyranyl, pyrrolidinyl, pyrrolidinonyl, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiophenyl, tetrahydrothiophenyl-oxide, tetrahydrothiophenyl-dioxide, thietanyl, thietanyl-oxide, thietanyl-dioxide, and thioxothiazolidinonyl, wherein each cycloalkyl, azetidinyl, 2,5-dioxoimidazolidinyl, 2,4-dioxo-1,3-diazaspiro[4.4]nonanylisoxazolidinonyl, imidazolidinonyl, isoxazolidinonyl, morpholinyl, oxazolidinonyl, oxetanyl, piperazinyl, piperidinyl, pyranyl, pyrrolidinyl, pyrrolidinonyl, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiophenyl, tetrahydrothiophenyl-oxide, tetrahydrothiophenyl-dioxide, thietanyl, thietanyl-oxide, thietanyl-dioxide, and thioxothiazolidinonyl may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , oxo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, C(═O)O(C 1 -C 4 )alkyl, (C═O)NH(C 1 -C 4 )alkyl, (C═O)NH(C 1 -C 4 )haloalkyl, C(═O)(C 3 -C 6 )cyclopropyl, C(═O)(C 1 -C 4 )haloalkyl, C(═O)(C 1 -C 4 )alkyl(C 1 -C 4 )alkoxy, and (C 1 -C 4 )alkyl-morpholinyl;

(Q) Q 1 and Q 2 are each independently selected from the group consisting of O and S; and

N-oxides, 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 is selected from the group consisting of H and Cl.

3. A molecule according to claim 1 , wherein R 2 is selected from the group consisting of H, Cl, Br, CH 3 , and CF 3 .

4. A molecule according to claim 1 , wherein R 3 is selected from the group consisting of H, F, Cl, CH 3 , CF 3 , and OCF 3 .

5. A molecule according to claim 1 , wherein R 4 is selected from the group consisting of H, F, Cl, Br, CH 3 , and CF 3 .

6. A molecule according to claim 1 , wherein R 5 , R 6 , R 9 , R 10 , R 11 , R 12 , and R 13 are H.

7. A molecule according to claim 1 , wherein R 7 is Cl.

8. A molecule according to claim 1 , wherein R 8 is Cl.

9. A molecule according to claim 1 , wherein R 13 is selected from the group consisting of H, CI, and CF 3 .

10. A molecule according to claim 1 , wherein R 15 is selected from the group consisting of H and CH 3 .

11. A molecule according to claim 1 , wherein R 16 is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, azetidinyl, morpholinyl, oxetanyl, pyranyl, tetrahydrothiophenyl, thietanyl, thietanyl-oxide, and thietanyl-dioxide,

wherein each cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, azetidinyl, morpholinyl, oxetanyl, pyranyl, tetrahydrothiophenyl, thietanyl, thietanyl-oxide, and thietanyl-dioxide, may be optionally substituted with one or more substituents selected from the group consisting of H, F, CN, C(═O)OC(CH 3 ) 3 , and C(═O)CF 3 .

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

13. A 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, Br, CH 3 , and CF 3 ;

(C) R 3 is selected from the group consisting of H, F, Cl, CH 3 , and CF 3 , OCF 3 ;

(D) R 4 is selected from the group consisting of H, F, Cl, Br, CH 3 , and CF 3 ;

(E) R 5 is H;

(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) R 10 is H;

(K) R 11 is H;

(L) R 12 is H;

(M) R 13 is selected from the group consisting of H, F, Cl, and CF 3 ;

(N) R 14 is H;

(O) R 15 is selected from the group consisting of H and CH 3 ;

(P) R 16 is selected from the group consisting of (C 3 -C 8 )cycloalkyl, azetidinyl, morpholinyl, oxetanyl, pyranyl, tetrahydrothiophenyl, thietanyl, thietanyl-oxide, and thietanyl-dioxide, wherein each cycloalkyl, azetidinyl, morpholinyl, oxetanyl, pyranyl, tetrahydrothiophenyl, thietanyl, thietanyl-oxide, and thietanyl-dioxide, may be optionally substituted with one or more substituents selected from the group consisting of H, F, CN, C(═O)O(C 1 -C 4 )alkyl, C(═O)(C 3 -C 6 )cyclopropyl, C(═O)(C 1 -C 4 )haloalkyl, and C(═O)(C 1 -C 4 )alkyl(C 1 -C 4 )alkoxy; and

(Q) Q 1 and Q 2 are O.

14. A composition comprising:

(a) a molecule according to claim 1 : and

(b) an active ingredient.

15. A composition comprising:

(a) a molecule according to claim 13 : and

(b) an active ingredient.

16. A molecule according to claim 1 wherein said molecule is one of the following molecules

No.

Structure

F4

F5

F9

F10

F11

F15

F16

F17

17. A process comprising applying to a locus a pesticidally effective amount of a molecule according to claim 1 .

18. A process according to claim 17 wherein said pest is a chewing pest.

19. A molecule according to claim 1 wherein said molecule is one of the following molecules

No.

Structure

F1

F2

F3

F4

F5

F6

F7

F8

F9

F10

F11

F12

F13

F14

F15

F16

F17

F18

F19

F20

F21

F22

F23

F24

F25

F26

F27

F28

F29

F30

F31

F32

F33

F34

F35

F36

F37

F38

F39

F40

F41

F42

F43

F44

F45

F46

F47

F48

F49

F50

F51

F52

F53

F54

F55

F56

F57

F58

F59

F60

F61

F62

F63

F64

F65

F66

F67

F68

F69

F70

F71

F72

F73

F74

F75

F76

F77

F78

F79

F80

F81

F82

F83

F84

F85

F86

F87

F88

F89

F90

F91

F92

PF1

PF2

PF3

PF4

PF5

PF6

PF7

PF8

PF9

PF12

PF14

PF18

PF19

PF20

PF21

PF22

PF23

PF28

PF29

PF30

PF31

PF32

PF33

PF34

PF36

PF37

PF41

PF42

PF43

PF44

PF45

20. A composition comprising:

(a) a molecule according to claim 16 : and

(b) an active ingredient.

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: ECKELBARGER, JOSEPH D.; KNUEPPEL, DANIEL I.; HEEMSTRA, RONALD J.; ROSS, RONALD; DEKORVER, KYLE; GRAY, KAITLYN; VEDNOR, PETER; MARTIN, TIMOTHY P.; HUNTER, RICKY; DEMETER, DAVID A.; TRULLINGER, TONY K.; BAUM, ERICH; BENKO, ZOLTAN; CHOY, NAKYEN; CROUSE, GARY; DAEUBLE, JOHN F., SR.; LI, FANGZHENG; NISSEN, JEFF; RIENER, MICHELLE; SPARKS, TOM; WESSELS, FRANK; YAP, MAURICE
To: DOW AGROSCIENCES LLC
Reel/Frame 038389/0295 →