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US 12,685,312 B2Granted
Sulfonamide apyrase inhibitors
AssigneeTexas Crop Science, Inc.
InventorsJohn Clough, Tanya Sabharwal, Simon Hiebert, Jeffrey D. Fowler, Matthew Duncton
Life of this patent
Estimating the term…
Abstract
Disclosed herein are apyrase inhibitors of Formula (I): Also disclosed herein are methods for using the disclosed inhibitors, including in methods for protecting crops from pests. In one aspect the apyrase inhibitors are useful for enhancing the activity of pesticides for the protection of crops from pathogens and to support crop yield.
Claims41
A method for inhibiting apyrase, comprising contacting the apyrase with a compound of the formula
- wherein
- L1 is selected from —C(O)N(Ra)— and —N(Ra)C(O)—;
- L2 is selected from —S(O)2N(Ra)— and —N(Ra)S(O)2—;
- wherein R1 is selected from C1-6 alkyl optionally substituted with one or more Ra and Rb, aryl optionally substituted with one or more R3, aralkyl optionally substituted with one or more R3, heterocyclyl optionally substituted with one or more Rd and heteroaryl optionally substituted with one or more R3;
- R2 is selected from C1-6 alkyl aryl and heteroaryl, each optionally substituted with one or more Ra and Rb;
- R3 is independently selected from Ra, Rb, —ORa substituted with one or more of the same or different Ra or Rb, or —(CH2)m—Rb, —(CHRa)m—Rb, —O—(CH2)m—Rb, —S—(CH2)m—Rb, —O—CHRaRb, —O—CRa(Rb)2, —O—(CHRa)m—Rb, —O—(CH2)m—CH[(CH2)mRb]Rb, —S—(CHRa)m—Rb, —C(O)NH—(CH2)m—Rb, —C(O)NH—(CHRa)m—Rb, —O—(CH2)m—C(O)NH—(CH2)m—Rb;
- each Ra is independently selected from the group consisting of hydrogen, C1-6 alkyl, C1-6 haloalkyl, C3-8 cycloalkyl, C6-10 aryl, C5-10 heteroaryl, C6-16 arylalkyl, 2-6 membered heteroalkyl and 3-8 membered heterocyclylalkyl, or Ra together with the nitrogen and the R1 or R2 attached thereto forms a heterocyclyl optionally substituted with one or more Rd, or forms a heteroaryl optionally substituted with one or more R3
- Z is selected from halogen, C1-6 alkyl, —ORa, and C1-6 haloalkyl;
- Rb is independently selected from the group consisting of ═O, —ORd, halogen, C1-3 haloalkyloxy, —OCF3, ═S, —SRd, ═NRd, ═NORd, —NRcRc, —SF5, halogen, —CF3, —CN, —NO2, —S(O)Rd, —S(O)2Rd, —S(O)2ORd, —S(O)NRcRc, —S(O)2NRcRc, —OS(O)Rd, —OS(O)2Rd, —OS(O)2ORd, —OS(O)2NRcRc, —C(O)Rd, —C(O)ORd, —C(O)NRcRc, —C(NH)NRcRc, —C(NRa)NRcRc, —C(NOH)Ra, —C(NOH)NRcRc, —OC(O)Rd, —OC(O)ORd, —OC(O)NRcRc, —OC(NH)NRcRc, —OC(NRa)NRcRc, —[NHC(O)]nRd, —[NRaC(O)]nRd, —[NHC(O)]nORd, —[NRaC(O)]nORd, —[NHC(O)]nNRcRc, —[NRaC(O)]nNRcRc, —[NHC(NH)]nNRcRc and —[NRaC(NRa)]nNRcRc;
- each Rc is independently Ra, or, alternatively, two Rc are taken together with the nitrogen atom to which they are bonded to form a 5 to 10-membered heterocyclylalkyl or heteroaryl which may optionally include one or more of the same or different additional heteroatoms and which may optionally be substituted with one or more of the same or different Re groups;
- each Rd is independently hydrogen or C1-6 alkyl;
- each Re is independently halogen, C1-6 alkyl or —C(O)Rd;
- each m is independently an integer from 1 to 3;
- and
- each n is independently an integer from 0 to 3;
- provided that the compound does not have the formula
13 more elements
A composition, comprising
- a fungicide;
- a compound of the formula
- wherein
- L1 is selected from —C(O)N(Ra)— and —N(Ra)C(O)—;
- L2 is selected from —S(O)2N(Ra)— and —N(Ra)S(O)2—;
- wherein R1 is selected from C1-6 alkyl optionally substituted with one or more Ra and Rb, aryl optionally substituted with one or more R3, aralkyl optionally substituted with one or more R3, heterocyclyl optionally substituted with one or more Rd and heteroaryl optionally substituted with one or more R3;
- R2 is selected from C1-6 alkyl aryl and heteroaryl, each optionally substituted with one or more Ra and Rb;
- R3 is independently selected from Ra, Rb, —ORa substituted with one or more of the same or different Ra or Rb, or —(CH2)m—Rb, —(CHRa)m—Rb, —O—(CH2)m—Rb, —S—(CH2)m—Rb, —O—CHRaRb, —O—CRa(Rb)2, —O—(CHRa)m—Rb, —O—(CH2)m—CH[(CH2)mRb]Rb, —S—(CHRa)m—Rb, —C(O)NH—(CH2)m—Rb, —C(O)NH—(CHRa)m—Rb, —O—(CH2)m—C(O)NH—(CH2)m—Rb;
- each Ra is independently selected from the group consisting of hydrogen, C1-6 alkyl, C1-6 haloalkyl, C3-8 cycloalkyl, C6-10 aryl, C5-10 heteroaryl, C6-16 arylalkyl, 2-6 membered heteroalkyl and 3-8 membered heterocyclylalkyl or Ra together with the nitrogen and the R1 or R2 attached thereto forms a heterocyclyl optionally substituted with one or more Rd, or forms a heteroaryl optionally substituted with one or more R3;
- Z is selected from halogen, C1-6 alkyl, —ORa, and C1-6 haloalkyl;
- Rb is independently selected from the group consisting of ═O, —ORd, halogen, C1-3 haloalkyloxy, —OCF3, ═S, —SRd, —NRd, ═NORd, —NRcRc, —SF5, halogen, —CF3, —CN, —NO2, —S(O)Rd, —S(O)2Rd, —S(O)2ORd, —S(O)NRcRc, —S(O)2NRcRc, —OS(O)Rd, —OS(O)2Rd, —OS(O)2ORd, —OS(O)2NRcRc, —C(O)Rd, —C(O)ORd, —C(O)NRcRc, —C(NH)NRcRc, —C(NRa)NRcRc, —C(NOH)Ra, —C(NOH)NRcRc, —OC(O)Rd, —OC(O)ORd, —OC(O)NRcRc, —OC(NH)NRcRc, —OC(NRa)NRcRc, —[NHC(O)]nRd, —[NRaC(O)]nRd, —[NHC(O)]nORd, —[NRaC(O)]nORd, —[NHC(O)]nNRcRc, —[NRaC(O)]nNRcRc, —[NHC(NH)]nNRcRc and —[NRaC(NRa)]nNRcRc;
- each Rc is independently Ra, or, alternatively, two Rc are taken together with the nitrogen atom to which they are bonded to form a 5 to 10-membered heterocyclylalkyl or heteroaryl which may optionally include one or more of the same or different additional heteroatoms and which may optionally be substituted with one or more of the same or different Re groups;
- each Rd is independently hydrogen or C1-6 alkyl;
- each Re is independently halogen, C1-6 alkyl or —C(O)Rd;
- each m is independently an integer from 1 to 3;
- and
- each n is independently an integer from 0 to 3;
- provided that the compound does not have the formula
- and
- a phytologically acceptable carrier.
17 more elements
A pesticidal composition, comprising
- a pesticide;
- a compound of the formula
- wherein
- L1 is selected from —C(O)N(Ra)— and —N(Ra)C(O)—;
- L2 is selected from —S(O)2N(Ra)— and —N(Ra)S(O)2—;
- wherein R1 is selected from C1-6 alkyl optionally substituted with one or more Ra and Rb, aryl optionally substituted with one or more R3, aralkyl optionally substituted with one or more R3, heterocyclyl optionally substituted with one or more Rd and heteroaryl optionally substituted with one or more R3;
- R2 is selected from C1-6 alkyl aryl and heteroaryl, each optionally substituted with one or more Ra and Rb;
- R3 is independently selected from Ra, Rb, —ORa substituted with one or more of the same or different Ra or Rb, or —(CH2)m—Rb, —(CHRa)m—Rb, —O—(CH2)m—Rb, —S—(CH2)m—Rb, —O—CHRaRb, —O—CRa(Rb)2, —O—(CHRa)m—Rb, —O—(CH2)m—CH[(CH2)mRb]Rb, —S—(CHRa)m—Rb, —C(O)NH—(CH2)m—Rb, —C(O)NH—(CHRa)m—Rb, —O—(CH2)m—C(O)NH—(CH2)m—Rb;
- each Ra is independently selected from the group consisting of hydrogen, C1-6 alkyl, C1-6 haloalkyl, C3-8 cycloalkyl, C6-10 aryl, C5-10 heteroaryl, C6-16 arylalkyl, 2-6 membered heteroalkyl and 3-8 membered heterocyclylalkyl or Ra together with the nitrogen and the R1 or R2 attached thereto forms a heterocyclyl optionally substituted with one or more Rd, or forms a heteroaryl optionally substituted with one or more R3;
- Z is selected from halogen, C1-6 alkyl, —ORa, and C1-6 haloalkyl;
- Rb is independently selected from the group consisting of ═O, —ORd, halogen, C1-3 haloalkyloxy, —OCF3, ═S, —SRd, ═NRd, ═NORd, —NRcRc, —SF5, halogen, —CF3, —CN, —NO2, —S(O)Rd, —S(O)2Rd, —S(O)2ORd, —S(O)NRcRc, —S(O)2NRcRc, —OS(O)Rd, —OS(O)2Rd, —OS(O)2ORd, —OS(O)2NRcRc, —C(O)Rd, —C(O)ORd, —C(O)NRcRc, —C(NH)NRcRc, —C(NRa)NRcRc, —C(NOH)Ra, —C(NOH)NRcRc, —OC(O)Rd, —OC(O)ORd, —OC(O)NRcRc, —OC(NH)NRcRc, —OC(NRa)NRcRc, —[NHC(O)]nRd, —[NRaC(O)]nRd, —[NHC(O)]nORd, —[NRaC(O)]nORd, —[NHC(O)]nNRcRc, —[NRaC(O)]nNRcRc, —[NHC(NH)]nNRcRc and —[NRaC(NRa)]nNRcRc;
- each Rc is independently Ra, or, alternatively, two Rc are taken together with the nitrogen atom to which they are bonded to form a 5 to 10-membered heterocyclylalkyl or heteroaryl which may optionally include one or more of the same or different additional heteroatoms and which may optionally be substituted with one or more of the same or different Re groups;
- each Rd is independently hydrogen or C1-6 alkyl;
- each Re is independently halogen, C1-6 alkyl or —C(O)Rd,
- each m is independently an integer from 1 to 3;
- and
- each n is independently an integer from 0 to 3;
- provided that the compound does not have the formula
- and
- a phytologically acceptable carrier.
17 more elements
Dependencies are inferred from the claim text.