IP Library › Granted Patent US 10,638,756

Granted Patent B2

US 10,638,756 · App. 15/939,341 · Granted May 5, 2020

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

Inventors: Paul R. LePlae, Jr. (Brownsburg, IN); Thomas Barton (Indianapolis, IN); Xin Gao (Carmel, IN); James E. Hunter (Indianapolis, IN); William C. Lo (Fishers, IN); Joshodeep Boruwa (Guwahati, IN); Raghuram Tangirala (Bengaluru, IN); Gerald B. Watson (Zionsville, IN); John Herbert (Brownsburg, IN); David A. Demeter (Fishers, IN); Hemant Joshi (Navi Mumbai, IN)

Assignee: DOW AGROSCIENCES LLC

A01N37/46 A01N37/10 A01N37/28 A01N37/34 A01N43/10 A01N43/38 A01N43/40 A01N43/50 A01N43/54 A01N43/58 A01N43/60 A01N43/653 A01N43/66 A01N43/713 A01N43/78

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Quick Facts

Patent No.: US 10,638,756
App. No.: 15/939,341
Granted: May 5, 2020
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 (264)

1. A molecule having the following formula

wherein:

(A) R 1 is selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkenyl-O-(C 1 -C 6 )alkyl, (C 2 -C 6 )alkynyl, (C 3 -C 6 )cycloalkyl, C(═O)H, SR x , SOR x , SO 2 R x , wherein R x is selected from the group consisting of (C 1 -C 6 )alkyl and (C 1 -C 6 )haloalkyl;

(B) R 2 is selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkenyl-O-(C 1 -C 6 )alkyl, (C 2 -C 6 )alkynyl, (C 3 -C 6 )cycloalkyl, C(═O)H, SR x , SOR x , SO 2 R x , wherein R x is selected from the group consisting of (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, and (C 3 -C 6 )cycloalkyl;

(C) R 3 is selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkenyl-O-(C 1 -C 6 )alkyl, (C 2 -C 6 )alkynyl, (C 3 -C 6 )cycloalkyl, C(═O)H, SR x , SOR x , SO 2 R x , wherein R x is selected from the group consisting of (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, and (C 3 -C 6 )cycloalkyl;

(D) R 4 is selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkenyl-O-(C 1 -C 6 )alkyl, (C 2 -C 6 )alkynyl, (C 3 -C 6 )cycloalkyl, C(═O)H, SR x , SOR x , SO 2 R x , wherein R x is selected from the group consisting of (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, and (C 3 -C 6 )cycloalkyl;

(E) R 5 is selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkenyl-O-(C 1 -C 6 )alkyl, (C 2 -C 6 )alkynyl, (C 3 -C 6 )cycloalkyl, C(═O)H, SR x , SOR x , SO 2 R x , wherein R x is selected from the group consisting of (C 1 -C 6 )alkyl and (C 1 -C 6 )haloalkyl;

(F) R 6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy;

(G) R 7 is (C 1 -C 6 )haloalkyl;

(H) R 8 is F;

(I) R 9 is selected from the group consisting of (O), H, F, Cl, Br, I, CN, NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkenyl-O-(C 1 -C 6 )alkyl, (C 2 -C 6 )alkynyl, (C 3 -C 6 )cycloalkyl, C(═O)H, SR x , SOR x , SO 2 R x , wherein R x is selected from the group consisting of (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, and (C 3 -C 6 )cycloalkyl;

(J) R 10 is selected from the group consisting of (O), F, Cl, Br, I, CN, NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkenyl-O-(C 1 -C 6 )alkyl, (C 2 -C 6 )alkynyl, (C 3 -C 6 )cycloalkyl, C(═O)H, SR x , SOR x , SO 2 R x , wherein R x is selected from the group consisting of (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, and (C 3 -C 6 )cycloalkyl;

(K) R 11 is selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkenyl-O-(C 1 -C 6 )alkyl, (C 2 -C 6 )alkynyl, (C 3 -C 6 )cycloalkyl, C(═O)H, SR x , SOR x , SO 2 R x , wherein R x is selected from the group consisting of (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, and (C 3 -C 6 )cycloalkyl;

(L) R 12 is selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkenyl-O-(C 1 -C 6 )alkyl, (C 2 -C 6 )alkynyl, (C 3 -C 6 )cycloalkyl, C(═O)H, SR x , SOR x , SO 2 R x , wherein R x is selected from the group consisting of (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, and (C 3 -C 6 )cycloalkyl;

(M) Q 1 is selected from the group consisting of O and S;

(N) X 1 is selected from (1), (2), (3), and (4) wherein

(1) N(R 13 )N(R 14 )(R 15 ) wherein

(a) said R 13 is selected from the group consisting of H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkyl nitrile, (C 1 -C 6 )alkylC(═O)N(H)((C 1 -C 6 )alkyl), (C 1 -C 6 )alkylC(═O)N(H)((C 1 -C 6 )haloalkyl), (C 1 -C 6 )alkyl-O-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkyl(C 3 -C 6 )cycloalkyl, (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, (C 3 -C 6 )cycloalkyl, phenyl, heterocyclyl, substituted phenyl, and substituted heterocyclyl, wherein said substituted phenyl and substituted heterocyclyl are substituted with one or more substituents independently selected from the group consisting of F, Cl, Br, CN, NO 2 , NH 2 , OH, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 3 -C 6 )cycloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, C(═O)O(C 1 -C 6 )alkyl, oxo, C(═O)NH(C 1 -C 6 )alkyl, C(═O)NH(C 1 -C 6 )haloalkyl, S(C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, and N((C 1 -C 6 )alkyl) 2 ,

(b) said R 14 is selected from the group consisting of H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkyl nitrile, (C 1 -C 6 )alkylC(═O)N(H)((C 1 -C 6 )alkyl), (C 1 -C 6 )alkylC(═O)N(H)((C 1 -C 6 )haloalkyl), (C 1 -C 6 )alkyl-O-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkyl(C 3 -C 6 )cycloalkyl, (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, (C 3 -C 6 )cycloalkyl, phenyl, heterocyclyl, substituted phenyl, and substituted heterocyclyl, wherein said substituted phenyl and substituted heterocyclyl are substituted with one or more substituents independently selected from the group consisting of F, Cl, Br, CN, NO 2 , NH 2 , OH, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 3 -C 6 )cycloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, C(═O)O(C 1 -C 6 )alkyl, oxo, C(═O)NH(C 1 -C 6 )alkyl, C(═O)NH(C 1 -C 6 )haloalkyl, S(C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, and N((C 1 -C 6 )alkyl) 2 ,

(i) H, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkyl nitrile, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, wherein each of which may be substituted with, F, Cl, Br, I, CN, NO 2 , NH 2 , OH, (C 1 -C 6 )haloalkyl, (C 3 -C 6 )cycloalkyl, O(C 1 -C 6 )alkyl, O(C 1 -C 6 )haloalkyl, C(═O)O(C 1 -C 6 )alkyl, S(C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, and N((C 1 -C 6 )alkyl) 2 ,

(ii) (C 1 -C 6 )alkyl(C 3 -C 6 )cycloalkyl, (C 1 -C 6 )alkylphenyl, (C 3 -C 6 )cycloalkyl, phenyl, and heterocyclyl, wherein each of which may be substituted with, H to saturate an unsaturation, F, Cl, Br, I, CN, NO 2 , NH 2 , OH, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, O(C 1 -C 6 )alkyl, O(C 1 -C 6 )haloalkyl, C(═O)O(C 1 -C 6 )alkyl, oxo, S(C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, and N((C 1 -C 6 )alkyl) 2 ,

(2) N(R 16 )N═C(R 17 )(R 18 ) wherein R 16 and R 17 are H, and R 18 is selected from the group consisting of substituted or unsubstituted phenyl, and substituted or unsubstituted heterocyclyl, wherein said substituents on said substituted phenyl and substituted heterocyclyl are selected from the group consisting of wherein each of which may be substituted with, H to saturate an unsaturation, F, Cl, Br, I, CN, NO 2 , NH 2 , OH, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, O(C 1 -C 6 )alkyl, oxo, S(O) 2 (C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, and N((C 1 -C 6 )alkyl) 2 ,

(3) N═N(R 19 ) wherein said R 19 is selected from the group consisting of substituted or unsubstituted phenyl, and substituted or unsubstituted heterocyclyl, wherein said substituents on said substituted phenyl and substituted heterocyclyl are selected from the group consisting of wherein each of which may be substituted with, H to saturate an unsaturation, F, C 1 , Br, I, CN, NO 2 , NH 2 , OH, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, O(C 1 -C 6 )alkyl, oxo, S(O) 2 (C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, and N((C 1 -C 6 )alkyl) 2 ,

(4) N(H)—R 20 wherein R 20 is a heterocyclyl containing at least one nitrogen atom, wherein said nitrogen atom is bonded to N(H)-, wherein said heterocyclyl may be substituted with, H to saturate an unsaturation, F, Cl, Br, I, CN, NO 2 , NH 2 , OH, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, O(C 1 -C 6 )alkyl, oxo, S(O) 2 (C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, and N((C 1 -C 6 )alkyl) 2 ;

(O) 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;

and N-oxides, pro-insecticides, agriculturally acceptable acid addition salts, salt derivatives, solvates, ester derivatives, isotopes, resolved stereoisomers, and tautomers, of the molecules of Formula One

with the proviso that the following molecules are excluded

2. A molecule according to claim 1 wherein:

(F) R 6 is selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy;

(G) R 7 is (C 1 -C 6 )haloalkyl;

(H) R 8 is F;

(M) C 2 1 is selected from the group consisting of O and S;

(N) X 1 is selected from (1), (2), (3), and (4) wherein

(1) N(R 13 )N(R 14 )(R 15 ) wherein

3. A molecule according to claim 2 wherein:

(A) R 1 is H;

(B) R 2 is selected from the group consisting of H, F, Cl, Br, CF 3 , CHF 2 , OCF 3 , C(═O)H, C═CH 2 , and cyclopropyl;

(D) R 4 is selected from the group consisting of H, F, Cl, Br, CF 3 , CHF 2 , OCF 3 , C(═O)H, C═CH 2 , and cyclopropyl;

(E) R 5 is H;

(F) R 6 is H;

(G) R 7 is CF 3 ;

(H) R 8 is F;

(I) R 9 is H;

(J) R 10 is selected from the group consisting of CI, Br, CF 3 , and CH 3 ;

(K) R 11 is H;

(L) R 12 is H;

(M) Q 1 is O; and

(N) X 1 is selected from

(1) N(R 13 )N(R 14 )(R 15 ) wherein

(a) said R 13 is selected from the group consisting of H, CH 3 , CH 2 CH 3 , CH(CH 3 ) 2 , CH 2 CN, CH 2 C(═O)N(H)(CH 2 CF 3 ), CH 2 CH═CH 2 , CH 2 —O—CH 3 , CH 2 cyclopropyl, cyclopropyl, propargyl, dichloropyridazinyl, and methylthiazolyl,

(b) said R 14 is selected from the group consisting of H, CH 3 , CH 2 CH 3 , CH(CH 3 ) 2 , CH 2 CN, CH 2 C(═O)N(H)(CH 2 CF 3 ), CH 2 CH═CH 2 , CH 2 -O—CH 3 , CH 2 cyclopropyl, cyclopropyl, propargyl, dichloropyridazinyl, and methylthiazolyl,

(i) H, CH 3 , CH 2 CH 2 , C(CH 3 ) 3 , CH 2 C(CH 3 ) 3 , CH 2 CH 2 CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH 2 CF 3 , CH 2 CH 2 CH 2 CF 3 , CH 2 CH 2 CN, wherein each of which may be substituted with, F, Cl, Br, CN, NO 2 , NH 2 , OH, CF 3 , OCH 3 , C(═O)OCH 3 , SCH 3 , S(O) 2 CH 3 , S(O)CH 3 , and N(CH 3 ) 2 ,

(ii) CH 2 -cyclopropyl, CH 2 -phenyl, cyclohexyl, cyclopentyl, imidazolyl, phenyl, pyrazinyl, pyridazinyl, pyridinyl, pyrimidinyl, tetrahydrothiophenyl, tetrazolyl, thiazolyl, thienyl, and 1,3,5-triazinyl, wherein each of which may be substituted with, H to saturate an unsaturation, F, Cl, Br, CN, NO 2 , NH 2 , OH, CH 3 , CH 2 CH 3 , CF 3 , OCH 3 , C(═O)OCH 3 , oxo, SCH 3 , S(O) 2 CH 3 , S(O)CH 3 , and N(CH 3 ) 2 ;

(2) N(H)N═C(H)(R 18 ) wherein R 18 is phenyl or a heterocyclyl, wherein each of which may be substituted with, H to saturate an unsaturation, F, Cl, Br, CN, NO 2 , NH 2 , OH, CH 3 , CH 2 CH 3 , CF 3 , OCH 3 , oxo, S(O) 2 CH 3 , S(O)CH 3 , and N(CH 3 ) 2 ,

(3) N═N(R 19 ) wherein said R 19 is phenyl or a heterocyclyl, wherein each of which may be substituted with, H to saturate an unsaturation, F, Cl, Br, CN, NO 2 , NH 2 , OH, CH 3 , CH 2 CH 3 , CF 3 , OCH 3 , oxo, S(O) 2 CH 3 , S(O)CH 3 , and N(CH 3 ) 2 ,

(4) N(H)—R 20 wherein R 20 is selected from the group consisting of indolyl, imidazolyl, pyrrolyl, thiomorpholino, and triazolyl, wherein each of which may be substituted with, H to saturate an unsaturation, F, Cl, Br, CN, NO 2 , NH 2 , OH, CH 3 , CH 2 CH 3 , CF 3 , OCH 3 , oxo, S(O) 2 CH 3 , S(O)CH 3 , and N(CH 3 ) 2 .

4. A molecule according to claim 2 , wherein said molecule is selected from group consisting of the following molecules

No.

Structure

F10

F11

F12

F13

F14

F15

F16

F17

F18

F19

F20

F21

F26

F27

F28

F29

F30

F31

F32

F33

F34

F35

F37

F38

F39

F40

F41

F42

F43

F44

F45

F49

F50

F51

F52

F54

F55

F56

F57

F58

F59

F60

F61

F62

F63

F68

F70

F71

F73

F74

F75

F77

F78

F79

F82

F83

F84

F85

F86

F89

F90

F91

F92

F93

F94

F95

F96

F97

F98

F99

F100

F101

F102

F103

F104

F105

F106

F107

F109

F110

F111

F112

F113

F114

F116

F117

F118

F120

F121

F122

F123

F125

F126

F128

F129

F130

F132

F133

F134

F135

F136

F137

F138

F140

F141

F142

F143

F144

F145

F146

F147

F148

F149

F150

F151

F152

F155

F156

F157

F158

F159

F160

F162

F163

F164

F165

F166

F167

F168

F169

F170

F171

F172

F173

F174

F175

F176

F177

F178

F179

F180

F182

F183

F184

F185

F186

F187

F188

F189

F190

F191

F192

5. A composition comprising a molecule according to claim 2 and one or more active ingredients.

6. A composition comprising a molecule according to claim 2 and one or more active ingredients wherein at least one active ingredient is selected from AIGA.

7. A composition comprising a molecule according to claim 2 and one or more active ingredients wherein at least one active ingredient is selected from AIGA-2.

8. A composition comprising a molecule according to claim 2 and one or more active ingredients wherein at least one active ingredient is selected from AIGA-3.

9. A composition comprising a molecule according to claim 2 and one or more active ingredients wherein at least one active ingredient is selected from AIGA-4.

10. A composition according to claim 5 wherein the weight ratio of