IP Library › Granted Patent US 9,795,140

Granted Patent B2

US 9,795,140 · App. 15/092,646 · Granted Oct 24, 2017

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

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Patent No.: US 9,795,140
App. No.: 15/092,646
Granted: Oct 24, 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 (223)

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) 2 (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 (Q), 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 (Q), (C 1 -C 8 )alkyl, (C 1 -C 8 )alkyl-O-(C 1 -C 8 )alkyl, (C 1 -C 8 )alkyl(C 3 -C 8 )cycloalkyl, (C 1 -C 8 )alkylphenyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 1 -C 8 )haloalkyl, (C 1 -C 8 )alkyl-S-(C 1 -C 8 )alkyl, (C 1 -C 8 )alkyl-S(O)-(C 1 -C 8 )alkyl, (C 1 -C 8 )alkyl-S(O) 2 -(C 1 -C 8 )alkyl, O-phenyl, O-(C 2 -C 8 )alkenyl, O-(C 1 -C 8 )alkyl (C 3 -C 8 )cycloalkyl, O-(C 1 -C 8 )alkylphenyl, (C 1 -C 8 )alkyl-O-(C 1 -C 8 )alkyl(C 3 -C 8 )cycloalkyl, (C 1 -C 8 )alkyl-O-(C 1 -C 8 )haloalkyl, (C 1 -C 8 )alkyl-C(═O)NH-(C 1 -C 8 )haloalkyl, (C 1 -C 8 )alkyl-NHC(O)-(C 1 -C 8 )alkyl, (C 1 -C 8 )alkyl-S-(C 1 -C 8 )haloalkyl, (C 1 -C 8 )alkyl-S(O)-(C 1 -C 8 )haloalkyl, (C 1 -C 8 )alkyl-S(O) 2 -(C 1 -C 8 )haloalkyl, and (C 1 -C 8 )alkyl-S(O) 2 -NH 2 ,

wherein each alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, and phenyl, 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 , (C 1 -C 8 )alkyl, (C 1 -C 8 )alkoxy, (C 1 -C 8 )haloalkyl, N((C 1 C 8 )alkyl) 2 , C(O)O(C 1 -C 8 )alkyl, benzothioenyl, 2,3-dihydro-1H-imidazolonyl, furanyl, pyrazolyl, pyridinyl, thiazolyl, and triazolyl;

(Q) R 15 and R 16 together can optionally form a 2- to 5-membered saturated or unsaturated, hydrocarbyl link, which may contain one or more heteroatoms selected from the group consisting of nitrogen, sulfur, and oxygen,

wherein said hydrocarbyl link may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NH 2 , and NO 2;

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

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

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

5. A molecule according to claim 1 , wherein R 1 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 , and R 14 are each independently H.

6. A molecule according to claim 1 , wherein R 7 is selected from the group consisting of Cl and Br.

7. A molecule according to claim 1 , wherein R 8 is selected from the group consisting of Cl and Br.

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

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

10. A molecule according to claim 1 , wherein R 16 is selected from the group consisting of CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 OCH 2 CH 2 , CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 , CH 2 CH(CH 3 ) 2 , CH 2 cyclopropyl, CH 2 CH 2 cyclopropyl, CH 2 cyclobutyl, CH 2 phenyl, CH 2 CH 2 phenyl, CH 2 C═CH, CH 2 C═CH, CH 2 CF 3 , CH 2 CHF 2 , CH 2 CH 2 CF 3 , CH 2 CF 2 CF 3 , CH 2 CH 2 CH 2 CF 3 , CH 2 CH 2 CF 2 CF 3 , CH 2 CF 2 CF 2 CF 3 , CH 2 CH 2 CH 2 CH 2 F, CH 2 CH 2 SCH 3 , CH 2 CH 2 S(O)CH 3 , CH 2 CH 2 S(O) 2 CH 3 , C(CH 3 ) 2 CH 2 S(O) 2 CH 3 , Ophenyl, OCH 2 CH═CH 2 , OCH 2 cyclopropyl, OCH 2 phenyl, CH 2 CH 2 OCH 2 cyclopropyl, CH 2 CH 2 CH 2 OCH 2 CF 3 , CH 2 C(═O)NHCH 2 CF 3 , or CH 2 CH 2 NHC(═O)CH 3 ,

wherein each CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 , cyclopropyl, cyclobutyl, and phenyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, CN, C(CH 3 ) 3 , CF 3 , OCH 3 , OCH 2 CH 3 , N(CH 3 ) 2 , and pyridinyl.

11. A molecule according to claim 1 , wherein R 15 and R 16 together are —CH 2 CH 2 CF 2 CH 2 —.

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 H;

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

(D) R 4 is Cl;

(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, 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 CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 OCH 2 CH 2 , CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 , CH 2 CH(CH 3 ) 2 , CH 2 cyclopropyl, CH 2 CH 2 cyclopropyl, CH 2 cyclobutyl, CH 2 phenyl, CH 2 CH 2 phenyl, CH 2 C═CH, CH 2 C═CH, CH 2 CF 3 , CH 2 CHF 2 , CH 2 CH 2 CF 3 , CH 2 CF 2 CF 3 , CH 2 CH 2 CH 2 CF 3 , CH 2 CH 2 CF 2 CF 3 , CH 2 CF 2 CF 2 CF 3 , CH 2 CH 2 CH 2 CH 2 F, CH 2 CH 2 SCH 3 , CH 2 CH 2 S(O)CH 3 , CH 2 CH 2 S(O) 2 CH 3 , C(CH 3 ) 2 CH 2 S(O) 2 CH 3 , Ophenyl, OCH 2 CH═CH 2 , OCH 2 cyclopropyl, OCH 2 phenyl, CH 2 CH 2 OCH 2 cyclopropyl, CH 2 CH 2 CH 2 OCH 2 CF 3 , CH 2 C(═O)NHCH 2 CF 3 , and CH 2 CH 2 NHC(═O)CH 3 ,

(Q) R 15 and R 16 together are a 4 -membered saturated, hydrocarbyl link, wherein said hydrocarbyl link is substituted with one or more F; and

(R) Q l 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 process comprising applying to a locus a pesticidally effective amount of a molecule according to claim 1 .

17. A process according to claim 16 wherein said pest is a chewing pest.

18. A process according to claim 16 wherein said pest is a sap-feeding pest.

19. A molecule according to claim 1 wherein said molecule is selected from the following

No.

Structure

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

F78

F79

F84

F85

F86

F87

F88

F91

F92

F93

F94

F95

F96

F97

F98

F99

F100

F102

F103

F104

F105

F106

F107

F108

F109

F111

F112

F113

F114

F115

F116

F117

F118

F119

F120

F121

F122

F123

F124

F125

F126

F127

F128

F129

F130

F131

F132

F133

F134

F135

PF1

PF2

PF3

PF4

PF5

PF6

PF7

PF9

PF10

PF11

PF12

PF13

PF14

PF15

PF16

20. A molecule according to claim 1 wherein said molecule is selected from the following

No.

Structure

F15

F28

F30

F35

F38

F39

F40

F45

F46

F47

F49

PF16

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: MARTIN, TIMOTHY P.; ECKELBARGER, JOSEPH D.; ROSS, RONALD; DEKORVER, KYLE; HEEMSTRA, RONALD J.; KNUEPPEL, DANIEL I.; VEDNOR, PETER; 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 038389/0230 →