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CN-122003403-A - Pyridazin-3-one-4-yl oxadiazines as novel bactericides

CN122003403ACN 122003403 ACN122003403 ACN 122003403ACN-122003403-A

Abstract

The present invention relates to pyridazin-3-one-4-yl-oxadiazines and their use for combating phytopathogenic microorganisms, such as phytopathogenic fungi. The invention also relates to processes and intermediates for preparing these compounds.

Inventors

  • L Nicholas
  • TSUCHIYA TOMOMI
  • V. THOMAS
  • M Gore Gus

Assignees

  • 拜耳公司

Dates

Publication Date
20260508
Application Date
20240919
Priority Date
20231011

Claims (13)

  1. 1. A compound of formula (I) and N-oxides, salts, hydrates, and hydrates of salts and N-oxides thereof: , Wherein the method comprises the steps of R 3 and R 4 are independently hydrogen, fluorine or C 1 -C 4 -alkyl, R 5 is hydrogen or C 1 -C 4 -alkyl, L is a direct bond or C 1 -C 4 -alkylene, Wherein the method comprises the steps of The C 1 -C 4 -alkylene group being optionally substituted by 1 or 2 substituents L SA , L SA is fluorine, and the fluorine is selected from the group consisting of fluorine, Or (b) Two substituents L SA bonded to the same carbon atom form a cyclopropyl ring or cyclobutyl ring together with the carbon atom to which they are attached, R 6 is C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3-to 14-membered heterocyclyl, 5-to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5-to 14-membered heteroaryloxy, 3-to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylthio, C 6 -C 14 -arylthio, 5-to 14-membered heteroarylthio, 3-to 14-membered heterocyclylthio, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, Wherein C 1 -C 3 -alkoxy and C 1 -C 3 -haloalkoxy are substituted with 1 substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3-to 14-membered heterocyclyl and 5-to 14-membered heteroaryl, Wherein the C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3-to 14-membered heterocyclyl and 5-to 14-membered heteroaryl are in turn optionally substituted with 1 to 3R 6S substituents, Wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3-to 14-membered heterocyclyl, 5-to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5-to 14-membered heteroaryloxy, 3-to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylthio, C 6 -C 14 -arylthio, 5-to 14-membered heteroarylthio and 3-to 14-membered heterocyclylthio are optionally substituted by 1 to 3 substituents R 6S , Wherein the method comprises the steps of R 6S is independently selected from halogen, cyano, nitro, hydroxy, mercapto, pentafluorothio, oxo, methylene, halomethylene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 6 -cycloalkylthio, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 6 -C 14 -aryl, 5-OR 6-membered heteroaryl, 3-to 7-membered heterocyclyl, -C (=O) (OR 17 ) and-C (=O) N (R 18 ) 2 , Wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylthio and C 1 -C 6 -haloalkylthio are in turn optionally substituted with 1 to 3 substituents independently selected from fluorine, chlorine, hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl, And Wherein C 3 -C 6 -cycloalkylthio, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 6 -C 14 -aryl, 5-or 6-membered heteroaryl and 3-to 7-membered heterocyclyl are in turn optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy, And wherein R 17 and R 18 are independently hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, Wherein said C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl is in turn optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro, hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl, R 7 is selected from the group consisting of C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -Cyclomethyl, methylformyl, tert-butylformyl, 2- (dimethylamino) -2-oxo-ethyl, 2- (methylamino) -2-oxo-ethyl, phenyl, thiazolyl, oxazolyl, pyrazolyl, triazolyl, imidazolyl, thienyl, isoxazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, pyridazinyl or triazinyl, wherein said phenyl, thiazolyl, oxazolyl, pyrazolyl, triazolyl, imidazolyl, thienyl, isoxazolyl, oxadiazolyl, thiadiazolyl, Any of pyridinyl, pyrimidinyl, pyridazinyl and triazinyl is unsubstituted or substituted with 1 or 2 substituents R 8 independently selected from halogen, mercapto, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, C 2 -C 4 -alkenyl, c 2 -C 4 -alkynyl or C 1 -C 3 -alkylsulfonyl, or R 7 is CR 12 R 13 R 14 , wherein R 12 and R 13 are independently selected from hydrogen or methyl, or R 12 and R 13 together with the carbon atom to which they are attached form cyclopropyl, and R 14 is selected from cyano, methylformyl, 2- (dimethylamino) -2-oxo-ethyl or 2- (methylamino) -2-oxo-ethyl, or R 14 is phenyl, heteroaryl selected from the group consisting of pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazolyl, thiazolyl, oxazolyl, imidazolyl, thienyl, furyl, isoxazolyl, oxadiazolyl and thiadiazolyl, or heterocyclyl selected from the group consisting of oxetanyl, azetidinyl, oxetanyl, aziridinyl, pyrrolidinyl, piperidinyl, piperazinyl, tetrahydrofuranyl, tetrahydropyranyl, morpholinyl and dioxane, wherein any of the phenyl, heteroaryl and heterocyclyl is unsubstituted or substituted with 1 or2 substituents R 9 independently selected from the group consisting of halogen, mercapto, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy, C 2 -C 4 -alkynyl or C 1 -C 4 -alkylsulfonyl; Q is phenyl, naphthyl, C 3 -C 10 -carbocyclyl, 5-to 10-membered heterocyclyl or 5-to 10-membered heteroaryl, Wherein phenyl, naphthyl, C 3 -C 10 -carbocyclyl, 5-to 10-membered heterocyclyl and 5-to 10-membered heteroaryl are optionally substituted by 1 to 3 substituents Q S , Wherein the method comprises the steps of Q S is independently selected from halogen, cyano, nitro, formyl, carboxyl, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, and, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, C 3 -C 6 -cycloalkyl, 3 to 7 membered heterocyclyl, phenyl, 5 or 6 membered heteroaryl, Wherein the method comprises the steps of The C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl are in turn optionally substituted with 1 to 3 substituents independently selected from cyano, cyano-group, or a salt thereof, Amino, nitro, hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl and 3-to 7-membered heterocyclyl, The C 3 -C 6 -cycloalkyl, 3-to 7-membered heterocyclyl, phenyl and 5-or 6-membered heteroaryl are in turn optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl and C 3 -C 6 -cycloalkyl.
  2. 2. The compound of formula (I) according to claim 1, and salts, hydrates and hydrates of salts thereof, wherein R 3 and R 4 are independently hydrogen, fluorine or methyl, R 5 is hydrogen, and the hydrogen atom, L is a direct bond, methylene, 1-ethylene or 1, 2-ethylene, Wherein the method comprises the steps of The methylene, 1-ethylene and 1, 2-ethylene groups being optionally substituted by 1 or 2 substituents L SA , L SA is fluorine, and the fluorine is selected from the group consisting of fluorine, Or (b) Two substituents L SA bonded to the same carbon atom form a cyclopropyl ring or cyclobutyl ring together with the carbon atom to which they are attached, R 6 is indanyl, 1,2,3, 4-tetrahydronaphthyl, phenyl, naphthyl, dihydrobenzofuranyl, dihydrobenzodioxanyl, furanyl, thienyl, indolyl or benzofuranyl, Wherein indanyl, 1,2,3, 4-tetrahydronaphthyl, phenyl, naphthyl, dihydrobenzofuranyl, dihydrobenzodioxanyl, furanyl, thienyl, indolyl and benzofuranyl are optionally substituted with 1 or 2R 6S substituents, Wherein, the R 6S is independently selected from the group consisting of fluoro, chloro, C 1 -C 4 -alkyl, difluoromethyl, trifluoromethyl, C 1 -C 4 -alkoxy, difluoromethoxy, trifluoromethoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, oxetanyl, tetrahydrofuranyl, pyrazolyl and pyridinyl, Wherein C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl are in turn optionally substituted with 1 or 2 substituents independently selected from hydroxy and C 1 -C 4 -alkoxy, And Wherein C 3 -C 6 -cycloalkyl, oxetanyl, tetrahydrofuranyl, pyrazolyl and pyridinyl are in turn optionally substituted with 1 or 2 substituents independently selected from fluoro, chloro and C 1 -C 4 -alkyl, R 7 is selected from C 1 -C 4 -alkyl or CR 12 R 13 R 14 , wherein R 12 and R 13 are independently selected from hydrogen or methyl, and R 14 is selected from cyano, methylformyl, 2- (methylamino) -2-oxo-ethyl, phenyl, heteroaryl selected from pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, thiazolyl, oxazolyl and imidazolyl, or heterocyclyl selected from pyrrolidinyl, piperidinyl and tetrahydropyranyl, wherein any of the phenyl, heteroaryl and heterocyclyl is unsubstituted or substituted with 1 or 2 substituents R 9 independently selected from fluoro, chloro, cyano, methyl, ethyl, methoxy or cyclopropyl; q is phenyl, thienyl or pyridyl, Wherein phenyl, thienyl and pyridyl are optionally substituted with 1 or 2 substituents Q S , Wherein the method comprises the steps of Q S is independently selected from halogen, C 1 -C 4 -alkyl, difluoromethyl, trifluoromethyl, C 1 -C 4 -alkoxy, difluoromethoxy, trifluoromethoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl and C 3 -C 6 -cycloalkyl, Wherein the method comprises the steps of The C 3 -C 6 -cycloalkyl is in turn optionally substituted with 1 or 2 substituents independently selected from fluoro, chloro and methyl.
  3. 3. The compound of formula (I) according to claim 1 or 2, and salts, hydrates and hydrates of salts thereof, wherein R 6 is a phenyl group, and the amino group, Wherein the phenyl is optionally substituted with 1 or 2R 6S substituents, Wherein the method comprises the steps of R 6S is independently selected from fluorine, chlorine, C 1 -C 4 -alkyl, difluoromethyl and trifluoromethyl.
  4. 4. A compound of formula (I) according to any one of claims 1-3 and salts, hydrates and hydrates of salts thereof, wherein R 3 and R 4 are hydrogen, R 5 is hydrogen, and the hydrogen atom, L is a methylene group, and the L is a methylene group, R 6 is a group of the formula: 、 、 Or (b) , Wherein the method comprises the steps of 1 Is the point of connection to L, R 6S1 is chlorine or methyl, and the alkyl is substituted by methyl, R 6S2 is chlorine or methyl, and the alkyl is substituted by methyl, R 7 is a methyl group, and the amino group is a methyl group, Q is a group of the formula: Wherein the method comprises the steps of 2 Is a point of attachment to an oxygen atom, Q S1 is hydrogen or fluorine, and, Q S2 is chloro, fluoro, methyl, trifluoromethyl or cyclopropyl.
  5. 5. A compound of formula (I) according to any one of claims 1-4, wherein the compound of formula (I) is selected from: -4- [ (5 RS) -5- (2-chloro-4-methylbenzyl) -5, 6-dihydro-4H-1, 2, 4-oxadiazin-3-yl ] -5- (3-chlorophenoxy) -2-methylpyridazin-3 (2H) -one, -5- (3-Cyclopropylphenoxy) -4- [ (5 RS) -5- (2, 4-dimethylbenzyl) -5, 6-dihydro-4H-1, 2, 4-oxadiazin-3-yl ] -2-methylpyridazin-3 (2H) -one, -5- (3-Chlorophenoxy) -4- [ (5 RS) -5- (3, 4-dimethylbenzyl) -5, 6-dihydro-4H-1, 2, 4-oxadiazin-3-yl ] -2-methylpyridazin-3 (2H) -one, -4- [ (5 RS) -5- (2-chloro-4-methylbenzyl) -5, 6-dihydro-4H-1, 2, 4-oxadiazin-3-yl ] -5- (3-cyclopropylphenoxy) -2-methylpyridazin-3 (2H) -one, -5- (3-Cyclopropylphenoxy) -4- [ (5 RS) -5- (3, 4-dimethylbenzyl) -5, 6-dihydro-4H-1, 2, 4-oxadiazin-3-yl ] -2-methylpyridazin-3 (2H) -one, -5- (3-Chloro-2-fluorophenoxy) -4- [ (5 RS) -5- (2-chloro-4-methylbenzyl) -5, 6-dihydro-4H-1, 2, 4-oxadiazin-3-yl ] -2-methylpyridazin-3 (2H) -one, -5- (3-Chloro-2-fluorophenoxy) -4- [ (5 RS) -5- (3, 4-dimethylbenzyl) -5, 6-dihydro-4H-1, 2, 4-oxadiazin-3-yl ] -2-methylpyridazin-3 (2H) -one.
  6. 6. A composition for controlling phytopathogenic harmful fungi, comprising at least one compound of formula (I) according to any of claims 1 to 5 and at least one carrier and/or surfactant.
  7. 7. Method for controlling harmful microorganisms in crop protection and in the protection of materials, characterized in that at least one compound of the formula (I) according to any one of claims 1 to 5 and/or a composition according to claim 6 is applied to the harmful microorganisms and/or their habitat.
  8. 8. The method of claim 7, wherein the harmful microorganism is a pathogenic oomycete or a phytopathogenic fungus selected from the group consisting of: the species of Leptosphaeria (Podosphaera), leptosphaeria (Sphaerotheca), leptosphaeria (Uncinula), leptosphaeria (Gymnosporangium), leptosphaeria (Hemileia), leptosphaeria (Phakopsora), puccinia (Puccinia), leptosphaeria (Uromyces), leptosphaeria (Albugo), The species of Peronospora (Bremia), peronospora (Peronospora), phytophthora (Phytophthora), axis Peronospora (Plasmopara), pseudoperonospora (Pseudomonas), pythum (Pythum), alternaria, cercospora (Cercospora), cladosporium (Cladiosporum), alternaria (Cochliobolus), cladosporium (Corynespora), cycloconium species, eimeria (Diaporthe) species, elsinoe (Elsinoe) species, pantoea (Gloeosporium) species, convolvulus (Glomerella) species, fabricius (Guignardia) species, leptosphaeria (Leptosphaeria) species, magnaporthe (Magnaporthe) species, microascum (Microdochium) species, mycosphaella (Phaeosphaeria) species, alternaria (Mycosphaella) species, alternaria (Mycosphaera) species, alternaria (Mynospora) species, The species of Nuclear, acremonium (Pyrenophora), acremonium (Ramularia), corallospora (Rhynchosporium), septoria (Septoria), phellinus (Stagonospora), ramaria (Typhula), ceriporia (Venturia), phanerochaete (Corticium), fusarium (Fusarium), acremonium (Gaeumannomyces), rhizopus (Plasmodiophora), rhizoctonia (Rhizoctonia), The species of Scopularium (Sarocladium), rhizoctonia (Sclerotium), tapesia, rhizopus (Thielaviopsis), aspergillus (Aspergillus), clavipita (CLAVICEPS), gibberella (Gibberella), monographella, fallospora (Stagospora), leptospira (Sphaceloteca), tilletia (Tilletia), henoniella (Urocystis), The species of the genus Bremia (Ustilago), the species of the genus Rhizoctonia (Monilinia), the species of the genus Penicillium (Penicillium), the species of the genus Rhizopus (Rhizopus), the species of the genus Sclerotinia (Sclerotinia), the species of the genus Verticillium (Verticilium), the species of the genus Rhapontium (Aphanomyces), the species of the genus Sclerotinia (Ascochyta), the species of the species Cladosporium (Cladosporium), the species of the genus Emerocallis (Macrophomina), the species of the species Phoma, the species of the species Phomopsis (Phomopsis), Pyricularia (Pycnaria) species, verticillium (Verticillium) species, saccharum (Nectria) species, exophiala (Exobasidium) species, exophiala (Taphrina) species, esca species, ganoderma (Ganoderma) species Helminthosporium (Helminthosporium) species, xanthomonas (Xanthomonas) species, pseudomonas (Pseudomonas) species, erwinia (Erwinia) species, pelargonium (Liberibacter) species, Xylem (Xyella) species, rhizoctonia (Ralstonia) species, dickeya (Dickeya) species, corynebacterium (Clavibacter) species, streptomyces (Streptomyces) species, colletotrichum gloeosporoides dematium var, truncatum, saccharomyces (Choanephora infundibulifera) trispora (synonym), dactuliophora glycines, The preparation method comprises the steps of performing navel vermicular spore (DRECHSLERA GLYCINI) in soybean, small pholiota nameko (Leptosphaerulina trifolii), pholiota nameko (Phyllosticta sojaecola), powdery mildew (Microsphaera diffusa), red leaf spot germ (Pyrenochaeta glycines), circular spore (Sphaceloma glycines), pholiota (Stemphylium botryosum), The composition comprises monocrotaline red shell (Calonectria crotalariae), mycoleptodiscus terrestris, tube-invasion new red shell (Neocosmospora vasinfecta) and brown rot germ (Phialophora gregata).
  9. 9. The method of claim 7 or 8, wherein the harmful microorganism is a phytopathogenic fungus selected from the group consisting of powdery mildew monocystis (Sphaerotheca fuliginea), alternaria alternata (ALTERNARIA ALTERNATA), pyricularia oryzae (Pyricularia oryzae), alternaria brassicae (ALTERNARIA BRASSICAE) and Fusarium yellow (Fusarium culmorum).
  10. 10. Use of one or more compounds of the formula (I) according to any one of claims 1 to 5 and/or of a composition according to claim 6 for controlling harmful microorganisms in crop protection and in the protection of materials.
  11. 11. Process for preparing compounds of formula (I-a) Wherein R 3 、R 4 、R 5 、R 6 、R 7 , L and Q are as defined in any one of claims 1 to 5, Characterized in that a compound of formula (1): Wherein R 7 and Q are as defined above, and U 1 is hydroxy, halogen or C 1 -C 6 -alkoxy, With an amine of formula (13) or one of its salts Wherein R 3 、R 4 、R 5 、R 6 and L are as defined above, and E 1 is a hydroxyl group or a halogen, W is hydrogen or an amino protecting group, such as t-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl) methyl, To obtain a compound of formula (14): , wherein R 3 、R 4 、R 5 、R 6 、R 7 、E 1 , L, W and Q are as defined above, The compound of formula (14) is then treated with a dehydrating agent, followed by treatment with hydroxylamine to form the compound of formula (15): , Wherein R 3 、R 4 、R 5 、R 6 、R 7 、E 1 , L, Q and W are as defined above, When E 1 is a hydroxyl group, it is, The compound of formula (15) is converted into a compound of formula (I-a) under the conditions of a photo-delay reaction, or When E 1 is a halogen atom, it is, The compound of formula (15) is converted to the compound of formula (I-a) in the presence of a base.
  12. 12. Compounds of formula (14) and formula (15): (14) A kind of electronic device (15) Wherein the method comprises the steps of R 3 、R 4 、R 5 、L、R 6 、R 7 and Q are as defined in any one of claims 1 to 5, E 1 is hydroxy or halogen, preferably hydroxy, chloro or bromo, E 2 is hydroxy, and W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl) methyl.
  13. 13. Compounds of formula (16) and formula (17): (16) A kind of electronic device (17) Wherein the method comprises the steps of R 3 、R 4 、R 5 、L、R 6 and R 7 are as defined in any one of claims 1 to 5, X is halogen, preferably chlorine or bromine, E 1 is hydroxy or halogen, preferably hydroxy, chloro or bromo, E 2 is hydroxy, and W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl) methyl.

Description

Pyridazin-3-one-4-yl oxadiazines as novel bactericides The present invention relates to pyridazin-3-one-4-yl-oxadiazines and their use for combating phytopathogenic microorganisms, such as phytopathogenic fungi. The invention also relates to processes and intermediates for preparing these compounds. Up to now, a number of crop protection agents have been developed which combat or prevent microbial infestation. However, there remains a need to develop new compounds in order to provide compounds which are effective against a broad spectrum of phytopathogenic microorganisms, such as fungi, which have low toxicity, high selectivity or can be used at low application rates, while still being effective against pests. It may also be desirable to have new compounds to prevent the emergence of resistance. The present invention provides novel compounds for controlling phytopathogenic microorganisms, such as fungi, which compounds have at least some of the above-mentioned advantages over known compounds and compositions. WO2020/127780、WO2021/245083、WO2021/249995、WO2021/245087、WO2021/255071、WO2023/213626、WO2023/099445、WO2024/089191、WO2024132895 And WO2024/132901 discloses oxadiazine compounds having different heterocyclic moieties as fungicides. Detailed Description A compound of formula (I) The present invention relates to compounds of formula (I) and N-oxides, salts, hydrates, and hydrates of salts and N-oxides thereof: , Wherein the method comprises the steps of R 3 and R 4 are independently hydrogen, fluorine or C 1-C4 -alkyl, R 5 is hydrogen or C 1-C4 -alkyl, L is a direct bond or C 1-C4 -alkylene, Wherein the method comprises the steps of The C 1-C4 -alkylene group being optionally substituted by 1 or 2 substituents L SA, L SA is fluorine, and the fluorine is selected from the group consisting of fluorine, Or (b) Two substituents L SA bonded to the same carbon atom form a cyclopropyl ring or cyclobutyl ring together with the carbon atom to which they are attached, R 6 is C 3-C12 -carbocyclyl, C 6-C14 -aryl, 3-to 14-membered heterocyclyl, 5-to 14-membered heteroaryl, C 3-C12 -carbocyclyloxy, C 6-C14 -aryloxy, 5-to 14-membered heteroaryloxy, 3-to 14-membered heterocyclyloxy, C 3-C12 -carbocyclylthio, C 6-C14 -arylthio, 5-to 14-membered heteroarylthio, 3-to 14-membered heterocyclylthio, C 1-C3 -alkoxy, C 1-C3 -haloalkoxy, Wherein C 1-C3 -alkoxy and C 1-C3 -haloalkoxy are substituted with 1 substituent selected from the group consisting of C 3-C12 -carbocyclyl, C 6-C14 -aryl, 3-to 14-membered heterocyclyl and 5-to 14-membered heteroaryl, Wherein the C 3-C12 -carbocyclyl, C 6-C14 -aryl, 3-to 14-membered heterocyclyl and 5-to 14-membered heteroaryl are in turn optionally substituted with 1 to 3R 6S substituents, Wherein C 3-C12 -carbocyclyl, C 6-C14 -aryl, 3-to 14-membered heterocyclyl, 5-to 14-membered heteroaryl, C 3-C12 -carbocyclyloxy, C 6-C14 -aryloxy, 5-to 14-membered heteroaryloxy, 3-to 14-membered heterocyclyloxy, C 3-C12 -carbocyclylthio, C 6-C14 -arylthio, 5-to 14-membered heteroarylthio and 3-to 14-membered heterocyclylthio are optionally substituted by 1 to 3 substituents R 6S, Wherein the method comprises the steps of R 6S is independently selected from halogen, cyano, nitro, hydroxy, mercapto, pentafluorothio, oxo, methylene, halomethylene, C 1-C6 -alkyl, C 1-C6 -haloalkyl, C 1-C6 -alkoxy, C 1-C6 -haloalkoxy, C 2-C6 -alkenyl, C 2-C6 -haloalkenyl, C 2-C6 -alkynyl, C 2-C6 -haloalkynyl, C 1-C6 -alkylthio, C 1-C6 -haloalkylthio, C 3-C6 -cycloalkylthio, C 3-C6 -cycloalkyl, C 3-C6 -cycloalkyloxy, C 6-C14 -aryl, 5-OR 6-membered heteroaryl, 3-to 7-membered heterocyclyl, -C (=O) (OR 17) and-C (=O) N (R 18)2, Wherein C 1-C6 -alkyl, C 1-C6 -haloalkyl, C 1-C6 -alkoxy, C 1-C6 -haloalkoxy, C 2-C6 -alkenyl, C 2-C6 -haloalkenyl, C 2-C6 -alkynyl, C 2-C6 -haloalkynyl, C 1-C6 -alkylthio and C 1-C6 -haloalkylthio are in turn optionally substituted with 1 to 3 substituents independently selected from fluorine, chlorine, hydroxy, C 1-C4 -alkoxy, C 1-C4 -haloalkoxy, C 3-C6 -cycloalkyl and C 3-C6 -halocycloalkyl, And Wherein C 3-C6 -cycloalkylthio, C 3-C6 -cycloalkyl, C 3-C6 -cycloalkyloxy, C 6-C14 -aryl, 5-or 6-membered heteroaryl and 3-to 7-membered heterocyclyl are in turn optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro, C 1-C4 -alkyl, C 1-C4 -haloalkyl, C 1-C4 -alkoxy and C 1-C4 -haloalkoxy, And wherein R 17 and R 18 are independently hydrogen, C 1-C4 -alkyl or C 1-C4 -haloalkyl, Wherein said C 1-C4 -alkyl or C 1-C4 -haloalkyl is in turn optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro, hydroxy, C 1-C4 -alkoxy, C 1-C4 -haloalkoxy, C 3-C6 -cycloalkyl and C 3-C6 -halocycloalkyl, R 7 is selected from the group consisting of C 1-C4 -alkyl, C 2-C4 -alkenyl, C 2-C4 -alkynyl, C 3-C6 -cycloalkyl, C 3-C6 -Cyclomethyl, methylformyl, tert-butylformyl, 2- (dimethylamino) -2-oxo-ethyl, 2- (methylamino) -2-oxo-ethyl, phenyl, thiazolyl, oxazolyl, pyraz