Apyrase inhibitors

A method for inhibiting apyrase, comprising contacting the apyrase with a compound of the formula

• or an agriculturally acceptable salt, solvate and/or N-oxide thereof, wherein R1 and R2 independently are selected from hydrogen, Ra, and Ra substituted with one or more Rb, Rd, or both;
• or R1 and R2 together form a 5- or 6-membered aliphatic, aromatic, heteroaliphatic or heteroaromatic ring optionally substituted with one or more R8;
• X is selected from O and —NR3—;
• R3 is hydrogen or C1-6 alkyl;
• Y is selected from —OR5, —NR4R5, —N(H)—O—R5, and —O—NR4R5;
• R4 is selected from hydrogen, Ra, and Ra substituted with one or more Rb, Rd, or both;
• R5 is selected from Ra optionally substituted with one or more R8, —(CH2)m—R8, —(CHRa)m—R8, —O—(CH2)m—R8, —CHRaR8, —O—CRa(R8)2, —O—(CHRa)m—R8;
• or R4 and R5 together with the nitrogen atom to which they are bonded, form a 5-10-membered heterocyclylalkyl, optionally containing 1, 2 or 3 additional heteroatoms selected from O, N and S, and optionally substituted by one or more Rb, Re, or both;
• each R8 is independently selected from Ra, Rb, Ra substituted with one or more Rb, and —ORa optionally substituted with one or more of the same or different Ra or Rb;
• each Ra is independently selected from the group consisting of C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, C3-8 cycloalkyl, C6-10 aryl, C5-10 heteroaryl, C6-16 arylalkyl, 2-6 membered heteroalkyl and 3-8 membered heterocyclylalkyl;
• Rb is independently selected from the group consisting of ═O, —ORa, halogen, C1-3 haloalkyloxy, —OCF3, —S, —SRd, =NRd, =NORd, —NRcRc, —SF5, halogen, —CF3, —CN, —NO2, —S(O)Rd, —S(O)2Rd, —S(O)2ORd, —N(H)S(O)2Rd, —S(O)NRcRc, —S(O)2NRcRe, —OS(O)Rd, —OS(O)2Rd, —OS(O)2ORd, —OS(O)2NRcRc, —C(O)Rd, —C(O)OR4, —C(O)NRcRc, —C(NH) NRcRc, —C(NRa) NRcRe, —C(NOH) Ra, —C(NOH) NRcRc, —OC(O)Rd, —OC(O)ORd, —OC(O)NRcRc, —OC(NH) NRcRc, —OC(NRa)NRcRc, —[NHC(O)]nRd, —[NRC(O)]nRd, [NHC(O)]nORd, —[NRaC(O)]nORd, —[NHC(O)]nNRcRc, —[NRC(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.