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EP-4739691-A1 - SUBSTITUTED PYRIDYL/PYRAZINYL DIHYDROPYRROLOTRIAZINE COMPOUNDS FOR COMBATTING PHYTOPATH-OGENIC FUNGI

EP4739691A1EP 4739691 A1EP4739691 A1EP 4739691A1EP-4739691-A1

Abstract

The present invention relates to the compounds of formula (I) wherein the variables are defined as given in the description and claims. The invention further relates to their use and composition.

Inventors

  • SEEBERGER, Philipp Georg Werner
  • LE VEZOUET, RONAN
  • ZIEGLER, Dorothee Sophia
  • GRAMMENOS, WASSILIOS
  • SELMANI, Aymane
  • MERGET, Benjamin Juergen
  • WINTER, CHRISTIAN
  • RIEDIGER, Nadine
  • KOCH, ANDREAS
  • LOHMANN, JAN KLAAS
  • DIETZ, JOCHEN

Assignees

  • BASF SE

Dates

Publication Date
20260513
Application Date
20240625

Claims (13)

  1. 1 . The compounds of formula I Z is N or CR 1 ; R 1 is hydrogen, halogen, CN, Ci-Ce-alkyl or Ci-Ce-halogenalkyl; R 2 is in each case independently selected from hydrogen, halogen, CN, Ci-Ce-alkyl, Ci-C6-halogenalkyl,C2-C6- alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Cs-Ce-cycloalkyl, O-Ci-Ce-alkyl, O-C 2 - Ce-alkenyl, O-C2-C6-alkynyl, Ci-Ce-halogenalkoxy, S-Ci-Ce-alkyl, S-C2-C6-alkenyl, S-C2-C6-alkynyl, N(H)-Ci- C 6 -alkyl, N(Ci-C 6 -alkyl) 2 , N(H)-C(=O)-Ci-C 6 -alkyl, N(Ci-C 6 -alkyl)-C(=O)-Ci-C 6 -alkyl, N(H)-C 2 -C 6 -alkenyl, N(C 2 -C6-alkenyl) 2 , N(H)-C 2 -C6-alkynyl, N(C 2 -Ce-alkynyl) 2 ; R 3 is in each case independently selected from hydrogen, halogen, CN, Ci-Ce-alkyl, Ci-Ce-halogenalkyl, C 2 -Ce- alkenyl, C 2 -C6-halogenalkenyl, C 2 -C6-alkynyl, C 2 -C6-halogenalkynyl, Cs-Ce-cycloalkyl, O-Ci-Ce-alkyl, O-C 2 - Ce-alkenyl, O-C 2 -C6-alkynyl, Ci-Ce-halogenalkoxy, S-Ci-Ce-alkyl, S-C 2 -C6-alkenyl, S-C 2 -C6-alkynyl, N(H)-Ci- C 6 -alkyl, N(Ci-C 6 -alkyl) 2 , N(H)-C(=O)-Ci-C 6 -alkyl, N(Ci-C 6 -alkyl)-C(=O)-Ci-C 6 -alkyl, N(H)-C 2 -C 6 -alkenyl, N(C 2 -C6-alkenyl) 2 , N(H)-C 2 -C6-alkynyl, N(C 2 -C6-alkynyl) 2 ; R 4 is hydrogen, halogen, CN, Ci-Ce-alkyl or Ci-Ce-halogenalkyl; R 5 is hydrogen, halogen, CN, Ci-Ce-alkyl, Ci-Ce-halogenalkyl, C 2 -C6-alkenyl, C 2 -C6-halogenalkenyl, C 2 -Ce- alkynyl, C 2 -C6-halogenalkynyl, Cs-Ce-cycloalkyl, phenyl or benzyl, heterocyclic aromatics and CH 2 - heterocyclic aromatics where the last-mentioned aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents R 5a ; where each R 5a is independently halogen, CN, Ci-Ce-alkyl, Ci-Ce-halogenalkyl or O-Ci-Ce-alkyl; R 6 is hydrogen, halogen, CN, Ci-Ce-alkyl, Ci-Ce-halogenalkyl, C 2 -Ce-alkenyl, C 2 -Ce-halogenalkenyl, C 2 -Ce- alkynyl, C 2 -Ce-halogenalkynyl, Cs-Ce-cycloalkyl, phenyl or benzyl, heterocyclic aromatics and CH 2 - heterocyclic aromatics where the last-mentioned aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents R 6a ; where each R 6a is independently halogen, CN, Ci-Ce-alkyl, Ci-Ce-halogenalkyl or O-Ci-Ce-alkyl; or R 5 and R 6 form together form together (=0) or (=S); or R 5 and R 6 , together with the carbon atom to which they are bound, form a 3-, 4-, 5- or 6-membered saturated carbocyclic ring or a 3-, 4-, 5- or 6-membered saturated heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from 0, N and S as ring members; where the carbocyclic or heterocyclic ring is unsubstituted or carries 1 , 2 or 3 substituents R 56 ; where each R 56 is independently halogen, Ci-Ce-alkyl or Ci-Ce-halogenalkyl; R 7 is hydrogen, CN, CH 2 CN, CH(CH 3 )CN, CH(=O), -C(=O)Ci-C 6 -alkyl, -C(=O)C 2 -C 6 -alkenyl, -C(=O)C 2 -C 6 - alkynyl, -C(=O)C 3 -C6-cycloalkyl, -C(=O)-N(H)Ci-C 6 -alkyl, -C(=O)-N(Ci-C 6 -alkyl) 2 , Ci-C 6 -alkyl, O-Ci-C 6 -alkyl, Ci-Ce-halogenalkyl, C 3 -C6-cycloalkyl, C 3 -C6-halogencycloalkyl, C 2 -C6-alkenyl, C 2 -C6-halogenalkenyl, C 2 -Ce- alkynyl, C 2 -C6-halogenalkynyl, -S(=O) 2 -R 7a , five- or six-membered heteroaryl, aryl, benzyl or CH 2 -heteroaryl; wherein heteroaryl contains 1 , 2 or 3 heteroatoms selected from N, 0 and S as ring members; wherein aryl and the phenyl ring in benzyl are unsubstituted or carry 1 , 2, 3, 4 or 5 substituents selected from the group consisting of CN, halogen, OH, Ci-Ce-alkyl, Ci-Ce-halogenalkyl, O-Ci-Ce-alkyl and O-Ci-Ce-halogenalkyl; wherein R 7a is Ci-Ce-alkyl, Ci-Ce-halogenalkyl, C 2 -C6-alkenyl, C 2 -C6-halogenalkenyl, C 2 -C6-alkynyl, C 2 -Ce- halogenalkynyl, phenyl or benzyl, where the phenyl ring in the two last-mentioned radicals is unsubstituted or carries 1 , 2 or 3 substituents each independently selected from the group consisting of halogen, Ci-Ce-alkyl, Ci-Ce-halogenalkyl, C 2 -C6-alkenyl, C 2 -C6-halogenalkenyl, C 2 - Ce-alkynyl and C 2 -C6-halogenalkynyl; X is in each case independently selected from halogen, CN, Ci-Ce-alkyl, Ci-Ce-halogenalkyl, C 2 -C6-alkenyl, C 2 - Ce-alkynyl, C 3 -C6-cycloalkyl, O-Ci-Ce-alkyl, Ci-Ce-halogenalkoxy, S(Ci-C6)alkyl, N(H)-Ci-C6-alkyl, N(Ci-Ce- alkyl) 2 , CH(=O), -C(=O)Ci-C 6 -alkyl, -C(=O)-O-Ci-C 6 -alkyl, -C(=O)-N(H)Ci-C 6 -alkyl, -C(=O)-N(Ci-C 6 -alkyl) 2 , 5- or 6-membered saturated carbocyclic ring, saturated heterocyclic ring, aromatic ring or heteroaromatic ring, wherein the heterocyclic ring and heteroaromatic ring contain 1, 2 or 3 heteroatoms selected from 0, N and S as ring members where the last-mentioned aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents X a ; where each X a is independently halogen, CN, Ci-Ce-alkyl, Ci-Ce-halogenalkyl, OH, O-Ci-Ce-alkyl, O-Ci-Ce- halogenalkyl, S-Ci-Ce-alkyl, N(H)-Ci-Ce-alkyl, N(Ci-C6-alkyl) 2 ; n is 0, 1 , 2 or 3; or the N-oxides, tautomers, stereoisomers or agriculturally acceptable salts thereof.
  2. 2. Compound of claim 1 , wherein Z is CR 1 and R 1 is hydrogen or CH 3 .
  3. 3. Compound of any one of claims 1 to 2, wherein R 2 is Br, C2-Ce-alky ny I or Ci-Ce-alkyl.
  4. 4. Compound of any one of claims 1 to 3, wherein R 3 is selected from CN, Ci-Ce-alkyl or Ci-Ce-halogenalkyl.
  5. 5. Compound of any one of claims 1 to 4, wherein R 4 is H.
  6. 6. Compound of any one of claims 1 to 5, wherein R 5 is Ci-Ce-alkyl.
  7. 7. Compound of any one of claims 1 to 6, wherein R 6 is Ci-Ce-alkyl.
  8. 8. Compound of any one of claims 1 to 7, wherein R 5 and R 6 form together with the C atoms to which they are bound a Ca-Ce-cycloalkyl.
  9. 9. Compound of any one of claims 1 to 8, wherein R 7 is selected from H, CN, CH2CN, Ci-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, benzyl.
  10. 10. Compound of any one of claims 1 to 9, wherein X is H.
  11. 11. A composition, comprising one compound of formula I, as defined in any of the claims 1 to 10, an N-oxide or an agriculturally acceptable salt thereof.
  12. 12. A method for combating phytopathogenic fungi, comprising treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack with an effective amount of at least one compound of formula I, as defined in any of the claims 1 to 10 or with a composition, as defined in any of the claim 11.
  13. 13. Seed, coated with at least one compound of the formula I, as defined in any of the claims 1 to 10 or an agriculturally acceptable salt thereof or with a composition, as defined in any of the claim 11, in an amount of from 0.1 to

Description

SUBSTITUTED PYRIDYL/PYRAZINYL DIHYDROPYRROLOTRIAZINE COMPOUNDS FOR COMBATTING PHYTOPATH-OGENIC FUNGI The present invention relates to new substituted pyridyl/pyrazinyl dihydropyrrolotriazine compounds and the N-oxides and the salts thereof as well as their use as fungicides. The invention also relates to the composition comprising at least one compound I, to the method for combating phytopathogenic fungi and to the seed coated with at least one compound of the formula I. It is well known, that in many cases, in particular at low application rates, the fungicidal activity of the products being on the market is unsatisfactory. Further, the ever-increasing risk of resistance occurring in market products is forcing researchers to search for new active compounds. Based on this, it was an objective of the present invention to provide compounds having improved activity and/or a broader activity spectrum against phytopathogenic fungi. Another object of the present invention is to provide fungicides with improved toxicological properties or with improved environmental fate properties. These and further objects are achieved by the substituted pyridyl/pyrazinyl dihydropyrrolotriazine compounds of formula (I), as defined below, and by their agriculturally suitable salts. Accordingly, the present invention relates to the compounds of formula I Z Is N or CR1; R1 is hydrogen, halogen, CN, Ci-Ce-alkyl or Ci-Ce-halogenalkyl; R2 is in each case independently selected from hydrogen, halogen, CN, Ci-Ce-alkyl, Ci-Ce-halogenalkyl,C2-Ce- alkenyl, C2-Ce-halogenalkenyl, C2-Ce-alkynyl, C2-Ce-halogenalkynyl, Cs-Ce-cycloalkyl, O-Ci-Ce-alkyl, O-C2-C6- alkenyl, O-C2-Ce-alkynyl, Ci-Ce-halogenalkoxy, S-Ci-Ce-alkyl, S-C2-Ce-alkenyl, S-C2-Ce-alkynyl, N(H)-Ci-Ce- alkyl, N(Ci-C6-alkyl)2. N(H)-C(=O)-Ci-C6-alkyl, N(Ci-C6-alkyl)-C(=O)-Ci-C6-alkyl N(H)-C2-C6-alkenyl, N(C2-C6- alkenyl)2, N(H)-C2-Ce-alkynyl, N(C2-Ce-alkynyl)2; R3 is in each case independently selected from hydrogen, halogen, CN, Ci-Ce-alkyl, Ci-Ce-halogenalkyl, C2-C6- alkenyl, C2-Ce-halogenalkenyl, C2-Ce-alkynyl, C2-Ce-halogenalkynyl, Cs-Ce-cycloalkyl, O-Ci-Ce-alkyl, O-C2-C6- alkenyl, O-C2-Ce-alkynyl, Ci-Ce-halogenalkoxy, S-Ci-Ce-alkyl, S-C2-Ce-alkenyl, S-C2-Ce-alkynyl, N(H)-Ci-Ce- alkyl, N(Ci-C6-alkyl)2. N(H)-C(=O)-Ci-C6-alkyl, N(Ci-Ce-alkyl)-C(=O)-Ci-C6-alkyl N(H)-C2-C6-alkenyl, N(C2-C6- alkenyl)2, N(H)-C2-Ce-alkynyl, N(C2-Ce-alkynyl)2; R4 is hydrogen, halogen, CN, Ci-Ce-alkyl or Ci-Ce-halogenalkyl; R5 is hydrogen, halogen, CN, Ci-Ce-alkyl, Ci-Ce-halogenalkyl, C2-Ce-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, Cs-Ce-cycloalkyl, phenyl or benzyl, heterocyclic aromatics and CH2- heterocyclic aromatics where the last-mentioned aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents R5a; where each R5a is independently halogen, CN, Ci-Ce-alkyl, Ci-Ce-halogenalkyl or O-Ci-Ce-alkyl; R6 is hydrogen, halogen, CN, Ci-Ce-alkyl, Ci-Ce-halogenalkyl, C2-Ce-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, Cs-Ce-cycloalkyl, phenyl or benzyl, heterocyclic aromatics and CH2- heterocyclic aromatics where the last-mentioned aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents R6a; where each R6a is independently halogen, CN, Ci-Ce-alkyl, Ci-Ce-halogenalkyl or O-Ci-Ce-alkyl; or R5 and R6 form together form together (=0) or (=S); or R5 and R6, together with the carbon atom to which they are bound, form a 3-, 4-, 5- or 6-membered saturated carbocyclic ring or a 3-, 4-, 5- or 6-membered saturated heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from 0, N and S as ring members; where the carbocyclic or heterocyclic ring is unsubstituted or carries 1 , 2 or 3 substituents R56; where each R56 is independently halogen, Ci-Ce-alkyl or Ci-Ce-halogenalkyl; R7 is hydrogen, CN, CH2CN, CH(CH3)CN, CH(=O), -C(=O)Ci-C6-alkyl, -C(=O)C2-C6-alkenyl, -C(=O)C2-C6- alkynyl, -C(=O)C3-C6-cycloalkyl, -C(=O)-N(H)Ci-C6-alkyl, -C(=O)-N(Ci-C6-alkyl)2, Ci-C6-alkyl, O-Ci-C6-alkyl, Ci-Ce-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, -S(=O)2-R7a, five- or six-membered heteroaryl, aryl, benzyl or CH2-heteroaryl; wherein heteroaryl contains 1 , 2 or 3 heteroatoms selected from N, 0 and S as ring members; wherein aryl and the phenyl ring in benzyl are unsubstituted or carry 1 , 2, 3, 4 or 5 substituents selected from the group consisting of CN, halogen, OH, Ci-Ce-alkyl, Ci-Ce-halogenalkyl, O-Ci-Ce-alkyl and O-Ci-Ce-halogenalkyl; wherein R7a is Ci-Ce-alkyl, Ci-Ce-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6- halogenalkynyl, phenyl or benzyl, where the phenyl ring in the two last-mentioned radicals is unsubstituted or carries 1 , 2 or 3 substituents each independently selected from the group consisting of halogen, Ci-Ce-alkyl, Ci-Ce-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2- Ce-alkynyl and C2-Ce-halogen