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

• US 10,638,756 B2
• Filed: 03/29/2018
• Issued: 05/05/2020
• Est. Priority Date: 03/31/2017
• Status: Active Grant

• Current Assignee: Corteva Agriscience LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: LePlae, Jr., Paul R., Barton, Thomas, Gao, Xin, Hunter, James E., Lo, William C., Boruwa, Joshodeep, Tangirala, Raghuram, Watson, Gerald B., Herbert, John, Demeter, David A., Joshi, Hemant
• Primary Examiner(s): Muresan, Ana Z
• Application Number:
  US15/939,341
• Publication Number:
  US 20180279612A1
• Time in Patent Office: 768 Days
• Field of Search: 564149
• CPC Class Codes: A01N 37/10 Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
• CPC Class Codes: A01N 37/28 containing the group; Thio analogues thereof
• CPC Class Codes: A01N 37/34 Nitriles
• CPC Class Codes: A01N 37/46 N-acyl derivatives
• CPC Class Codes: A01N 43/10 with sulfur as the ring hetero atom
• CPC Class Codes: A01N 43/38 condensed with carbocyclic rings
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/50 1,3-Diazoles; Hydrogenated 1,3-diazoles
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 43/58 1,2-Diazines; Hydrogenated 1,2-diazines
• CPC Class Codes: A01N 43/60 1,4-Diazines; Hydrogenated 1,4-diazines
• CPC Class Codes: A01N 43/653 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• CPC Class Codes: A01N 43/66 1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
• CPC Class Codes: A01N 43/713 having rings with four or more nitrogen atoms as the only ring hetero atoms
• CPC Class Codes: A01N 43/78 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• CPC Class Codes: Y02A 50/30 Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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

1. A molecule having the following formula

2. A molecule according to claim 1 wherein:

(A) R¹ is selected from the group consisting of H, F, Cl, Br, I, CN, NO₂, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkenyl-O-(C₁-C₆)alkyl, (C₂-C₆)alkynyl, (C₃-C₆)cycloalkyl, C(═

O)H, SR^x, SOR^x, SO₂R^x, wherein R^x is selected from the group consisting of (C₁-C₆)alkyl and (C₁-C₆)haloalkyl;

(B) R² is selected from the group consisting of H, F, Cl, Br, I, CN, NO₂, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkenyl-O-(C₁-C₆)alkyl, (C₂-C₆)alkynyl, (C₃-C₆)cycloalkyl, C(═

O)H, SR^x, SOR^x, SO₂R^x, wherein R^x is selected from the group consisting of (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, and (C₃-C₆)cycloalkyl;

(C) R³ is selected from the group consisting of H, F, Cl, Br, I, CN, NO₂, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkenyl-O-(C₁-C₆)alkyl, (C₂-C₆)alkynyl, (C₃-C₆)cycloalkyl, C(═

O)H, SR^x, SOR^x, SO₂R^x, wherein R^x is selected from the group consisting of (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, and (C₃-C₆)cycloalkyl;

(D) R⁴ is selected from the group consisting of H, F, Cl, Br, I, CN, NO₂, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkenyl-O-(C₁-C₆)alkyl, (C₂-C₆)alkynyl, (C₃-C₆)cycloalkyl, C(═

O)H, SR^x, SOR^x, SO₂R^x, wherein R^x is selected from the group consisting of (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, and (C₃-C₆)cycloalkyl;

(E) R⁵ is selected from the group consisting of H, F, Cl, Br, I, CN, NO₂, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkenyl-O-(C₁-C₆)alkyl, (C₂-C₆)alkynyl, (C₃-C₆)cycloalkyl, C(═

O)H, SR^x, SOR^x, SO₂R^x, wherein R^x is selected from the group consisting of (C₁-C₆)alkyl and (C₁-C₆)haloalkyl;

(F) R⁶ is selected from the group consisting of H, F, Cl, Br, I, CN, NO₂, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy;

(G) R⁷ is (C₁-C₆)haloalkyl;

(H) R⁸ is F;

(I) R⁹ is selected from the group consisting of (O), H, F, Cl, Br, I, CN, NO₂, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkenyl-O-(C₁-C₆)alkyl, (C₂-C₆)alkynyl, (C₃-C₆)cycloalkyl, C(═

O)H, SR^x, SOR^x, SO₂R^x, wherein R^x is selected from the group consisting of (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, and (C₃-C₆)cycloalkyl;

(J) R¹⁰ is selected from the group consisting of (O), F, Cl, Br, I, CN, NO₂, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkenyl-O-(C₁-C₆)alkyl, (C₂-C₆)alkynyl, (C₃-C₆)cycloalkyl, C(═

O)H, SR^x, SOR^x, SO₂R^x, wherein R^x is selected from the group consisting of (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, and (C₃-C₆)cycloalkyl;

(K) R¹¹ is selected from the group consisting of H, F, Cl, Br, I, CN, NO₂, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkenyl-O-(C₁-C₆)alkyl, (C₂-C₆)alkynyl, (C₃-C₆)cycloalkyl, C(═

O)H, SR^x, SOR^x, SO₂R^x, wherein R^x is selected from the group consisting of (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, and (C₃-C₆)cycloalkyl;

(L) R¹² is selected from the group consisting of H, F, Cl, Br, I, CN, NO₂, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkenyl-O-(C₁-C₆)alkyl, (C₂-C₆)alkynyl, (C₃-C₆)cycloalkyl, C(═

O)H, SR^x, SOR^x, SO₂R^x, wherein R^x is selected from the group consisting of (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, and (C₃-C₆)cycloalkyl;

(M) C₂¹ is selected from the group consisting of O and S;

(N) X¹ is selected from (1), (2), (3), and (4) wherein

(1) N(R¹³)N(R¹⁴)(R¹⁵) wherein

(a) said R¹³ is selected from the group consisting of H, (C₁-C₆)alkyl, (C₁-C₆)alkyl nitrile, (C₁-C₆)alkylC(═

O)N(H)((C₁-C₆)alkyl), (C₁-C₆)alkylC(═

O)N(H)((C₁-C₆)haloalkyl), (C₁-C₆)alkyl-O-(C₁-C₆)alkyl, (C₁-C₆)alkyl(C₃-C₆)cycloalkyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₁-C₆)haloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₃-C₆)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, NO₂, NH₂, OH, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₃-C₆)cycloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, C(═

O)O(C₁-C₆)alkyl, oxo, C(═

O)NH(C₁-C₆)alkyl, C(═

O)NH(C₁-C₆)haloalkyl, S(C₁-C₆)alkyl, S(O)₂(C₁-C₆)alkyl, S(O)(C₁-C₆)alkyl, and N((C₁-C₆)alkyl)₂,

(b) said R¹⁴ is selected from the group consisting of H, (C₁-C₆)alkyl, (C₁-C₆)alkyl nitrile, (C₁-C₆)alkylC(═

O)N(H)((C₁-C₆)alkyl), (C₁-C₆)alkylC(═

O)N(H)((C₁-C₆)haloalkyl), (C₁-C₆)alkyl-O-(C₁-C₆)alkyl, (C₁-C₆)alkyl(C₃-C₆)cycloalkyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₁-C₆)haloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₃-C₆)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, NO₂, NH₂, OH, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₃-C₆)cycloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, C(═

O)O(C₁-C₆)alkyl, oxo, C(═

O)NH(C₁-C₆)alkyl, C(═

O)NH(C₁-C₆)haloalkyl, S(C₁-C₆)alkyl, S(O)₂(C₁-C₆)alkyl, S(O)(C₁-C₆)alkyl, and N((C₁-C₆)alkyl)₂,

(c) said R¹⁵ is selected from the group consisting of

(i) H, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)alkyl nitrile, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, wherein each of which may be substituted with, F, Cl, Br, I, CN, NO₂, NH₂, OH, (C₁-C₆)haloalkyl, (C₃-C₆)cycloalkyl, O(C₁-C₆)alkyl, O(C₁-C₆)haloalkyl, C(═

O)O(C₁-C₆)alkyl, S(C₁-C₆)alkyl, S(O)₂(C₁-C₆)alkyl, S(O)(C₁-C₆)alkyl, and N((C₁-C₆)alkyl)₂,

(ii) (C₁-C₆)alkyl(C₃-C₆)cycloalkyl, (C₁-C₆)alkylphenyl, (C₃-C₆)cycloalkyl, phenyl, and heterocyclyl, wherein each of which may be substituted with, H to saturate an unsaturation, F, Cl, Br, I, CN, NO₂, NH₂, OH, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, O(C₁-C₆)alkyl, O(C₁-C₆)haloalkyl, C(═

O)O(C₁-C₆)alkyl, oxo, S(C₁-C₆)alkyl, S(O)₂(C₁-C₆)alkyl, S(O)(C₁-C₆)alkyl, and N((C₁-C₆)alkyl)₂,

(2) N(R¹⁶)N═

C(R¹⁷)(R¹⁸) wherein R¹⁶ and R¹⁷ are H, and R¹⁸ 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, NO₂, NH₂, OH, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, O(C₁-C₆)alkyl, oxo, S(O)₂(C₁-C₆)alkyl, S(O)(C₁-C₆)alkyl, and N((C₁-C₆)alkyl)₂,

(3) N═

N(R¹⁹) wherein said R¹⁹ 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, C₁, Br, I, CN, NO₂, NH₂, OH, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, O(C₁-C₆)alkyl, oxo, S(O)₂(C₁-C₆)alkyl, S(O)(C₁-C₆)alkyl, and N((C₁-C₆)alkyl)₂,

(4) N(H)—

R²⁰ wherein R²⁰ 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, NO₂, NH₂, OH, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, O(C₁-C₆)alkyl, oxo, S(O)₂(C₁-C₆)alkyl, S(O)(C₁-C₆)alkyl, and N((C₁-C₆)alkyl)₂; and

(O) R⁹ and R¹⁰ 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.

3. A molecule according to claim 2 wherein:

(A) R¹ is H;

(B) R² is selected from the group consisting of H, F, Cl, Br, CF₃, CHF₂, OCF₃, C(═

O)H, C═

CH₂, and cyclopropyl;

(C) R³ is selected from the group consisting of H, F, Cl, Br, CF₃, OCF₃, and C(OCH₂CH₃)(=CH₂);

(D) R⁴ is selected from the group consisting of H, F, Cl, Br, CF₃, CHF₂, OCF₃, C(═

O)H, C═

CH₂, and cyclopropyl;

(E) R⁵ is H;

(F) R⁶ is H;

(G) R⁷ is CF₃;

(H) R⁸ is F;

(I) R⁹ is H;

(J) R¹⁰ is selected from the group consisting of CI, Br, CF₃, and CH₃;

(K) R¹¹ is H;

(L) R¹² is H;

(M) Q¹ is O; and

(N) X¹ is selected from

(1) N(R¹³)N(R¹⁴)(R¹⁵) wherein

(a) said R¹³ is selected from the group consisting of H, CH₃, CH₂CH₃, CH(CH₃)₂, CH₂CN, CH₂C(═

O)N(H)(CH₂CF₃), CH₂CH═

CH₂, CH₂—

O—

CH₃, CH₂cyclopropyl, cyclopropyl, propargyl, dichloropyridazinyl, and methylthiazolyl,

(b) said R¹⁴ is selected from the group consisting of H, CH₃, CH₂CH₃, CH(CH₃)₂, CH₂CN, CH₂C(═

O)N(H)(CH₂CF₃), CH₂CH═

CH₂, CH₂-O—

CH₃, CH₂cyclopropyl, cyclopropyl, propargyl, dichloropyridazinyl, and methylthiazolyl,

(c) said R¹⁵ is selected from the group consisting of

(i) H, CH₃, CH₂CH₂, C(CH₃)₃, CH₂C(CH₃)₃, CH₂CH₂CH(CH₃)₂, CH₂CH(CH₃)₂, CH₂CF₃, CH₂CH₂CH₂CF₃, CH₂CH₂CN, wherein each of which may be substituted with, F, Cl, Br, CN, NO₂, NH₂, OH, CF₃, OCH₃, C(═

O)OCH₃, SCH₃, S(O)₂CH₃, S(O)CH₃, and N(CH₃)₂,

(ii) CH₂-cyclopropyl, CH₂-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, NO₂, NH₂, OH, CH₃, CH₂CH₃, CF₃, OCH₃, C(═

O)OCH₃, oxo, SCH₃, S(O)₂CH₃, S(O)CH₃, and N(CH₃)₂;

(2) N(H)N═

C(H)(R¹⁸) wherein R¹⁸ is phenyl or a heterocyclyl, wherein each of which may be substituted with, H to saturate an unsaturation, F, Cl, Br, CN, NO₂, NH₂, OH, CH₃, CH₂CH₃, CF₃, OCH₃, oxo, S(O)₂CH₃, S(O)CH₃, and N(CH₃)₂,

(3) N═

N(R¹⁹) wherein said R¹⁹ is phenyl or a heterocyclyl, wherein each of which may be substituted with, H to saturate an unsaturation, F, Cl, Br, CN, NO₂, NH₂, OH, CH₃, CH₂CH₃, CF₃, OCH₃, oxo, S(O)₂CH₃, S(O)CH₃, and N(CH₃)₂,

(4) N(H)—

R²⁰ wherein R²⁰ 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, NO₂, NH₂, OH, CH₃, CH₂CH₃, CF₃, OCH₃, oxo, S(O)₂CH₃, S(O)CH₃, and N(CH₃)₂.

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

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

(a) a molecule according to claim 2, to

(b) at least one active ingredient,

is selected from Table C.

11. A composition according to claim 6 wherein the weight ratio of

(a) a molecule according to claim 2, to

(b) at least one active ingredient selected from AIGA,

is selected from Table C.

12. A composition according to claim 7 wherein the weight ratio of

(a) a molecule according to claim 2, to

(b) at least one active ingredient selected from AIGA-2,

is selected from Table C.

13. A composition according to claim 8 wherein the weight ratio of

(a) a molecule according to claim 2, to

(b) at least one active ingredient selected from AIGA-3, is selected from Table C.

14. A composition according to claim 9 wherein the weight ratio of

(a) a molecule according to claim 2, to

(b) at least one active ingredient selected from AIGA-4, is selected from Table C.