Benzoxaborole fungicides
AssigneeSyngenta Participations AG
InventorsRamya RAJAN, Daniel STIERLI, Atul MAHAJAN, Renaud BEAUDEGNIES, Peter RENOLD
Life of this patent
Estimating the term…
Abstract
Compounds of formula (I) are as defined in the claims, and their use in compositions and methods for the control and/or prevention of microbial infection, particularly fungal infection, in plants and to processes for the preparation of these compounds.
Claims12
A method for controlling or preventing infestation of plants or plant propagation material and/or harvested food crops susceptible to microbial attack by treating plants or plant propagation material and/or harvested food crops with an effective amount of an oxaborole of general formula (I)
- wherein
- R1 is H, fluorine, chlorine, bromine, cyano, nitro, unsubstituted or substituted C1-C4alkyl, unsubstituted or substituted C1-C4alkoxy, unsubstituted or substituted or C1-C4haloalkyl;
- R3 is selected from H, unsubstituted or substituted C1-C4alkyl, unsubstituted or substituted C1-C4haloalkyl, unsubstituted or substituted six- to ten-membered aryl, unsubstituted or substituted five- to six-membered heteroary, unsubstituted or substituted C3-C7 cycloalkyl, or unsubstituted or substituted C3-C7 heterocycloalkyl;
- R2 is ═O, ═N—O—R5, ═N—NR6R7, ═N—N(CO)R6, ═N—NH(CO)NR8R9 or ═N—NH(CS)NR8R9
- R5, R6, R7, R8 and R9 are independently of each other hydrogen, unsubstituted or substituted C1-C10alkyl, unsubstituted or substituted C1-C10 haloalkyl, unsubstituted or substituted C1-C10alkoxy(C1-C10)alkyl, unsubstituted or substituted C2-C10alkenyl, unsubstituted or substituted C2-C10haloalkenyl, unsubstituted or substituted C2-C10alkynyl, unsubstituted or substituted C3-C7cycloalkyl(alkylene)(0-2), unsubstituted or substituted six- to ten-membered-aryl(alkylene)(0-2), or unsubstituted or substituted five- to ten-membered heteroaryl(alkylene)(0-2);
- wherein the substituents for the substituted aryl, heteroaryl, cycloalkyl and heterocycloalkyl moieties can be independently mono- or polysubstituted by substituents selected from the group consisting of halogen, hydroxy, nitro, cyano, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkenyl, C1-C6haloalkenyl, C1-C6alkinyl, C1-C6haloalkinyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkenyloxy, C1-C6haloalkenyloxy, C1-C6alkinyloxy, C1-C6haloalkinyl, C1-C6alkoxy-C1-C6alkyl, C1-C6haloalkoxy, C1-C6alkoximino, C1-C6alkylendioxy, —C(O)(C1-4 alkyl), —(C1-4 alkyl)-C(O)(C1-4 alkyl), —C(O)OH, —(C1-4 alkyl)-C(O)OH, unsubstituted or substituted six- to ten-membered-aryl(alkylene)(0-1) and unsubstituted or substituted six- to ten-membered-aryl(alkylene)(0-1)oxy;
- and wherein the substituents for the substituted cycloalkyl, heterocycloalkyl and alkyl can be independently mono- or polysubstituted by substituents selected from oxo, —OH, CN, NO2, F, Cl, C1-4alkoxy, —C(O)(C1-4 alkoxy), —C(O)(C1-4 alkyl), —C(O)—NH—(C1-4 alkyl), —C(O)—N(C1-4 alkyl)2, C1-4alkylamino, unsubstituted or substituted five- to ten-membered aryl, unsubstituted or substituted five- to six-membered heteroary, unsubstituted or substituted C3-C7 cycloalkyl, and unsubstituted or substituted C3-C7 heterocycloalkyl;
- and wherein the heterocycloalkyl and the heteroaryl contain 1 to 3 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for the ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms;
- or an agronomically acceptable salt, stereoisomer,
- diastereoisomer, enantiomer, tautomer, atriopisomer or N-oxide thereof.
A compound of formula (I)
- wherein
- R1 is H, fluorine, chlorine, bromine, cyano, nitro, unsubstituted or substituted C1-C4alkyl, unsubstituted or substituted C1-C4alkoxy, unsubstituted or substituted or C1-C4haloalkyl;
- R3 is selected from H, unsubstituted or substituted C1-C4alkyl, unsubstituted or substituted C1-C4haloalkyl, unsubstituted or substituted six- to ten-membered aryl, unsubstituted or substituted five- to six-membered heteroary, unsubstituted or substituted C3-C7 cycloalkyl, or unsubstituted or substituted C3-C7 heterocycloalkyl;
- R2 is ═O, ═N—O—R5, ═N—NR6R7, ═N—N(CO)R6, ═N—NH(CO)NR8R9 or ═N—NH(CS)NR8R9
- R5, R6, R7, R8 and R9 are independently of each other hydrogen, unsubstituted or substituted C1-C10alkyl, unsubstituted or substituted C1-C10 haloalkyl, unsubstituted or substituted C1-C10alkoxy(C1-C10)alkyl, unsubstituted or substituted C2-C10alkenyl, unsubstituted or substituted C2-C10haloalkenyl, unsubstituted or substituted C2-C10alkynyl, unsubstituted or substituted C3-C7cycloalkyl(alkylene)(0-2), unsubstituted or substituted six- to ten-membered-aryl(alkylene)(0-2), or unsubstituted or substituted five- to ten-membered heteroaryl(alkylene)(0-2);
- wherein the substituents for the substituted aryl, heteroaryl, cycloalkyl and heterocycloalkyl moieties can be independently mono- or polysubstituted by substituents selected from the group consisting of halogen, hydroxy, nitro, cyano, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkenyl, C1-C6haloalkenyl, C1-C6alkinyl, C1-C6haloalkinyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkenyloxy, C1-C6haloalkenyloxy, C1-C6alkinyloxy, C1-C6haloalkinyl, C1-C6alkoxy-C1-C6alkyl, C1-C6haloalkoxy, C1-C6alkoximino, C1-C6alkylendioxy, —C(O)(C1-4 alkyl), —(C1-4 alkyl)-C(O)(C1-4 alkyl), —C(O)OH, —(C1-4 alkyl)-C(O)OH, unsubstituted or substituted six- to ten-membered-aryl(alkylene)(0-1) and unsubstituted or substituted six- to ten-membered-aryl(alkylene)(0-1)oxy;
- and wherein the substituents for the substituted cycloalkyl, heterocycloalkyl and alkyl can be independently mono- or polysubstituted by substituents selected from oxo, —OH, CN, NO2, F, Cl, C1-4alkoxy, —C(O)(C1-4 alkoxy), —C(O)(C1-4 alkyl), —C(O)—NH—(C1-4 alkyl), —C(O)—N(C1-4 alkyl)2, C1-4alkylamino, unsubstituted or substituted five- to ten-membered aryl, unsubstituted or substituted five- to six-membered heteroary, unsubstituted or substituted C3-C7 cycloalkyl, and unsubstituted or substituted C3-C7 heterocycloalkyl;
- and wherein the heterocycloalkyl and the heteroaryl contain 1 to 3 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for the ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms;
- or an agronomically acceptable salt, stereoisomer,
- diastereoisomer, enantiomer, tautomer, atriopisomer or N-oxide thereof
- provided that
- if R1 is H then R5 is not methyl
- if R1 is H then R5 is not benzyl
- R1 and R3 are defined under formula I, provided that
- If R1 is H then —C(O)—R3 is not 6-CHO
- If R1 is H then —C(O)—R3 is not 4-CHO
- If R1 is 4-F then —C(O)—R3 is not 7-CHO
- If R1 is 4-OCH3 then —C(O)—R3 is not 7-CHO
- If R1 is H then —C(O)—R3 is not 5-CHO
- If R1 is H then —C(O)—R3 is not 7-CHO
- and if R1 is H then R3 is not butyl or phenyl.
A compound of formula (II)
- wherein R1 and R3 are defined under formula (I), provided that
- if R1 is H then —C(O)—R3 is not 6-CHO,
- if R1 is H then —C(O)—R3 is not 4-CHO,
- if R1 is 4-F then —C(O)—R3 is not 7-CHO,
- if R1 is 4-OCH3 then —C(O)—R3 is not 7-CHO
- if R1 is H then —C(O)—R3 is not 5-CHO,
- if R1 is H then —C(O)—R3 is not 7-CHO,
- and if R1 is H then R3 is not butyl or phenyl.
Dependencies are inferred from the claim text.