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US 2017/0000133 A1Published application
Benzoxaborole fungicides
AssigneeSyngenta Participations AG
InventorsRamya RAJAN, Peter RENOLD, Atul MAHAJAN, Daniel STIERLI, Renaud BEAUDEGNIES
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.
Claims11
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)
- R1 is H, fluorine, chlorine, bromine, cyano, nitro, unsubstituted or substituted C1-C4alkyl or unsubstituted or substituted C1-C4haloalkyl, unsubstituted or substituted C1-C4alkoxy, haloalkoxy;
- G=OR2, NR3R4
- R2, R3 and R4 independently are H, unsubstituted or substituted C1-C6alkyl, haloalkyl, six to 10 membered aryl, 1,3-benzodioxole-(C0-C2)—, five to ten membered heteroaryl which may be mono or bicyclic containing 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, C3-C6cycloalkyl, unsubstituted or substituted heterocycloalkyl containing 3 to 10 ring members containing 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, unsubstituted or substituted C1-C6alkoxy, unsubstituted or substituted C1-C6haloalkoxy, unsubstituted or substituted C2-C6alkenyl, unsubstituted or substituted C2-C6alkynyl, or
- R3 and R4 form together with the nitrogen to which they are attached a 3 to 9 ring containing 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,
- and wherein the substituents for the substituted aryl, heteroaryl, cycloalkyl, heterocycloalkyl and alkyl can be independently mono- or polysubstituted by substituents selected from oxo, —OH, CN, NO2, F, Cl, —SH, —S—C1-4 alkyl, —S(O)2—N— heteroaryl, —S(O)2—N-aryl, —C1-4 alkyl 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 heteroaryl, unsubstituted or substituted C3-C7 cycloalkyl, and unsubstituted or substituted C3-C7 heterocycloalkyl, 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, —S—S(O)2—OH, —S(O)2—OH, indolin, unsubstituted or substituted six- to ten-membered-aryl(alkylene)(0-3) and unsubstituted or substituted six- to ten-membered-aryl(alkylene)(0-3)oxy;
- wherein the heterocycloalkyl and heteroaryl containing 3 to 10 ring members containing 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
- 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, and or N-oxide thereof.
6 more elements
A compound of formula (I)
- wherein
- R1 is H, fluorine, chlorine, bromine, cyano, nitro, unsubstituted or substituted C1-C4alkyl or unsubstituted or substituted C1-C4haloalkyl, unsubstituted or substituted C1-C4alkoxy, haloalkoxy;
- G=OR2, NR3R4
- R2, R3 and R4 independently are H, unsubstituted or substituted C1-C6alkyl, haloalkyl, six to 10 membered aryl, 1,3-benzodioxole-(C0-C2)-, five to ten membered heteroaryl which may be mono or bicyclic containing 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, C3-C6cycloalkyl, unsubstituted or substituted heterocycloalkyl containing 3 to 10 ring members containing 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, unsubstituted or substituted C1-C6alkoxy, unsubstituted or substituted C1-C6haloalkoxy, unsubstituted or substituted C2-C6alkenyl, unsubstituted or substituted C2-C6alkynyl, or
- R3 and R4 form together with the nitrogen to which they are attached a 3 to 9 ring containing 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,
- and wherein the substituents for the substituted aryl, heteroaryl, cycloalkyl, heterocycloalkyl and alkyl can be independently mono- or polysubstituted by substituents selected from oxo, —OH, CN, NO2, F, Cl, —SH, —S—C1-4 alkyl, —S(O)2—N— heteroaryl, —S(O)2—N-aryl, —C1-4 alkyl 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 heteroaryl, unsubstituted or substituted C3-C7 cycloalkyl, and unsubstituted or substituted C3-C7 heterocycloalkyl, 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, —S—S(O)2—OH, —S(O)2—OH, indolin, unsubstituted or substituted six- to ten-membered-aryl(alkylene)(0-3) and unsubstituted or substituted six- to ten-membered-aryl(alkylene)(0-3)oxy;
- wherein the heterocycloalkyl and heteroaryl containing 3 to 10 ring members containing 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
- 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 the compound of formula (I) is not 1,3-dihydro-1-hydroxy-2,1-Benzoxaborole-7-carboxylic acid methyl ester or 3-dihydro-1-hydroxy-2,1-Benzoxaborole-7-carboxylic acid or 1,3-dihydro-1-hydroxy-N-phenyl-2,1-Benzoxaborole-6-carboxamide or 4-[[(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)carbonyl]amino]-benzenesulfonic acid or 1,3-dihydro-1-hydroxy-2,1-Benzoxaborole-6-carboxylic acid.
8 more elements
Dependencies are inferred from the claim text.