WO2020255946A1 - Composé 2,4-dioxo-1,4-dihydrothiénopyrimidine, bactéricide agricole et horticole - Google Patents

Composé 2,4-dioxo-1,4-dihydrothiénopyrimidine, bactéricide agricole et horticole Download PDF

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WO2020255946A1
WO2020255946A1 PCT/JP2020/023546 JP2020023546W WO2020255946A1 WO 2020255946 A1 WO2020255946 A1 WO 2020255946A1 JP 2020023546 W JP2020023546 W JP 2020023546W WO 2020255946 A1 WO2020255946 A1 WO 2020255946A1
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groups
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Inventor
陽平 宗井
頼人 ▲桑▼原
岩田　淳
貴昭 寺西
拓真 石原
千尋 西野
斎賀　睦幸
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Nippon Soda Co Ltd
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Nippon Soda Co Ltd
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Definitions

  • the present invention relates to 2,4-dioxo-1,4-dihydrothienopyrimidine compounds and fungicides for agriculture and horticulture. More specifically, the present invention contains a 2,4-dioxo-1,4-dihydrothienopyrimidine compound having excellent bactericidal activity, excellent safety, and industrially advantageous synthesis, and an active ingredient thereof. Regarding agricultural and horticultural fungicides.
  • the present application claims priority to Japanese Patent Application No. 2019-11199 filed on June 17, 2019, the contents of which are incorporated herein by reference.
  • Patent Document 1 discloses a compound represented by the formula (A) and the like.
  • Patent Document 2 discloses a compound represented by the formula (B) and the like.
  • Patent Document 3 discloses a compound represented by the formula (C) and the like.
  • Patent Document 4 discloses a compound represented by the formula (D) and the like.
  • Patent Document 5 discloses a compound represented by the formula (E) and the like.
  • Patent Document 6 discloses a compound represented by the formula (F) and the like. Further, Patent Document 7 discloses the use of a fungicide for agriculture and horticulture such as a compound represented by the formula (F).
  • Patent Document 8 discloses a compound represented by the formula (G) and the like.
  • Patent Document 9 discloses a compound represented by the formula (H) and the like.
  • An object of the present invention is that a 2,4-dioxo-1,4-dihydrothienopyrimidine compound (hereinafter, simply referred to as "thienopyrimidine compound”) has excellent bactericidal activity, is excellent in safety, and can be synthesized industrially advantageously. There is), as well as an agricultural and horticultural fungicide containing this as an active ingredient.
  • thienopyrimidine compound 2,4-dioxo-1,4-dihydrothienopyrimidine compound
  • R 1 is a substituted or unsubstituted C1-6 alkyl group.
  • R 3 , R 4 , R 5 and R 6 are independently hydrogen atoms or substituted or unsubstituted C1-6 alkyl groups.
  • R 3 and R 4 may be combined together to form a C2-6 alkylene group.
  • R 3 and R 5 may be combined together to form a C1-5 alkylene group.
  • R 5 and R 6 may be combined together to form a C2-6 alkylene group.
  • R 7 is a hydrogen atom, a hydroxyl group, a substituted or unsubstituted C1 to 6 alkoxy group, a substituted or unsubstituted C1 to 6 alkylcarbonyloxy group, or a substituted or unsubstituted C2 to 6 alkenyloxy group.
  • R 8 is a hydrogen atom.
  • R 7 and R 8 may be combined together to form a substituted or unsubstituted C1-6 alkoxyimino group.
  • X is a halogeno group or a substituted or unsubstituted C1-6 alkoxy group.
  • n is an integer of 0 to 5, and when n is 2 or more, X may be the same or different from each other.
  • Q is a group represented by the formula (Q-1), the formula (Q-2) or the formula (Q-3).
  • R g is a hydrogen atom and R h is a substituted or unsubstituted C1-6 alkyl group.
  • R e and R f are independently hydrogen atoms or substituted or unsubstituted C1 to 6 alkyl groups.
  • R i is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group.
  • the thienopyrimidine compound of the present invention has excellent bactericidal activity, reliable effect, excellent safety, and can be synthesized industrially advantageously.
  • the fungicide for agriculture and horticulture of the present invention has an excellent control effect, does not cause phytotoxicity to plants, and has little toxicity to humans, livestock and fish and has little influence on the environment.
  • the thienopyrimidine compound of the present invention is a compound represented by the formula (I) (hereinafter, may be referred to as compound (I)) or a salt of compound (I).
  • the term "unsubstituted” means that there are only parental groups. When only the name of the parent group is described, it means “unsubstituted” unless otherwise specified.
  • the term “substituted” means that any hydrogen atom of the parent group is substituted with a group having the same or different structure as the mother nucleus. Therefore, a "substituent” is another group attached to a parent group.
  • the number of substituents may be one or two or more. The two or more substituents may be the same or different.
  • the "substituent” is chemically acceptable and is not particularly limited as long as it has the effect of the present invention.
  • groups that can be “substituents” include the following groups. Halogeno groups such as fluoro group, chloro group, bromo group, iod group; C1-6 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc.
  • Alkyl group Vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group , 2-Pentenyl group, 3-Pentenyl group, 4-Pentenyl group, 1-methyl-2-butenyl group, 2-Methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4 -C2-6 alkenyl groups such as hexenyl group, 5-hexenyl group;
  • Ethynyl group 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group , 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group, etc.
  • C2-6 alkynyl groups C3-8 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cubicyl group; C3-8 cycloalkenyl groups such as 2-cyclopropenyl group, 2-cyclopentenyl group, 3-cyclohexenyl group, 4-cyclooctenyl group; C6-10 aryl groups such as phenyl group and naphthyl group; 5-membered heteroaryl groups such as pyrrolyl group, frill group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isooxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group; A 6-membered heteroaryl
  • Oxy group C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; C2-6 alkenyloxy groups such as vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group; C2-6 alkynyloxy groups such as ethynyloxy group and propargyloxy group; C6-10 aryloxy groups such as phenoxy group and naphthoxy group; 5- to 6-membered heteroaryloxy groups such as thiazolyloxy groups and pyridyloxy groups;
  • Carboxylic group comprising: Formylation group; C1-6 alkylcarbonyl groups such as acetyl group, propionyl group; Formyloxy group; C1-6 alkylcarbonyloxy groups such as acetyloxy group, propionyloxy group; C1-6 alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group;
  • C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group; C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group, 2-fluoro-1-butenyl group; C2-6 haloalkynyl groups such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group; C3-6 halocycloalkyl groups such as 3,3-difluorocyclobutyl group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group; C2-6 haloalken
  • Cyano group Nitro group; Amino group; C1-6 alkylamino groups such as methylamino group, dimethylamino group, diethylamino group; C6-10 arylamino groups such as anilino group and naphthylamino group; Formylamino group; C1-6 alkylcarbonylamino groups such as acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group; C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group; C1-6 alkyl sulfoxide imino groups such as S, S-dimethyl sulfoxide imino groups;
  • Aminocarbonyl group C1-6 alkylaminocarbonyl groups such as methylaminocarbonyl group, dimethylaminocarbonyl group, ethylaminocarbonyl group, i-propylaminocarbonyl group, etc.; Imino C1-6 alkyl groups such as iminomethyl group, 1-iminoethyl group, 1-imino-n-propyl group; Hydroxyimino C1-6 alkyl groups such as hydroxyiminomethyl group, 1- (hydroxyimino) ethyl group, 1- (hydroxyimino) -n-propyl group; C1-6 alkoxyimino C1-6 alkyl groups such as methoxyiminomethyl group, 1- (methoxyimino) ethyl group;
  • C1-6 alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group; C1-6 haloalkylthio groups such as trifluoromethylthio group, 2,2,2-trifluoroethylthio group; C2-6 alkenylthio groups such as vinylthio groups and allylthio groups; C2-6 alkynylthio groups such as ethynylthio group and propargylthio group; C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group; C1-6 haloalkylsulfinyl groups such as trifluoro
  • Tri-C1-6 alkylsilyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group; Tri-C6-10 arylsilyl groups such as triphenylsilyl groups
  • any hydrogen atom in the substituent may be substituted with a group having a different structure.
  • C1 to 6 indicate that the number of carbon atoms of the parent group is 1 to 6 or the like. This number of carbon atoms does not include the number of carbon atoms present in the substituent.
  • an ethoxybutyl group is classified as a C2 alkoxy C4 alkyl group because the parent group is a butyl group and the substituent is an ethoxy group.
  • R 1 is a substituted or unsubstituted C1-6 alkyl group.
  • the "C1 to 6 alkyl group" in R 1 may be a straight chain or a branched chain.
  • alkyl group a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, and a t-butyl group.
  • I-pentyl group neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.
  • a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo group; a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, C1-6 alkoxy groups such as n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group and the like.
  • Examples thereof include C1 to 6 alkoxy-substituted phenyl groups such as C1 to 6 haloalkoxy groups; cyano groups; methoxyphenyl groups and ethoxyphenyl groups.
  • Examples of the "C1 to 6 alkoxycarbonyl group" in R 2 include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, and a t-butoxycarbonyl group. it can.
  • a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group can be mentioned.
  • the "5- to 6-membered heteroaryl group" in R 2 includes a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group and a thiadiazolyl group.
  • a 5-membered heteroaryl group such as a tetrazolyl group
  • a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group and a triazinyl group can be mentioned.
  • a halogeno group such as a fluoro group, a chloro group, a bromo group and an iod group can be mentioned.
  • R 2 - R a in "formula”
  • CR a N-OR b
  • group represented by is hydrogen atom
  • R b is a substituted or unsubstituted C1 ⁇ 6 alkyl group.
  • Examples of the "substituted or unsubstituted C1 to 6 alkyl groups" in R b include the same ones specifically exemplified in R 1 .
  • R 3 , R 4 , R 5 , R 6 are independently hydrogen atoms or substituted or unsubstituted C1 to 6 alkyl groups.
  • R 3 , R 4 , R 5 and R 6 include the same ones specifically exemplified in R 1 .
  • R 3 and R 4 may be combined to form a C2-6 alkylene group.
  • Examples of the "C2 to 6 alkylene group" formed by R 3 and R 4 together include an ethylene group, a trimethylene group, a tetramethylene group, and a pentamethylene group.
  • R 3 and R 5 may be combined together to form a C1-5 alkylene group.
  • Examples of the "C1 to C5 alkylene group" formed by R 3 and R 5 together include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, and a pentamethylene group.
  • R 5 and R 6 may be combined to form a C2-6 alkylene group.
  • Examples of the "C2 to 6 alkylene group" formed by R 5 and R 6 together include those similar to those described above.
  • R 7 is a hydrogen atom, a hydroxyl group, a substituted or unsubstituted C1 to 6 alkoxy group, a substituted or unsubstituted C1 to 6 alkylcarbonyloxy group, or a substituted or unsubstituted C2 to 6 alkenyloxy group.
  • Examples of the "C1 to 6 alkoxy group" in R 7 include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, and a t-butoxy group. Can be mentioned.
  • Examples of the "C1 to 6 alkylcarbonyloxy group” in R 7 include an acetyloxy group and a propionyloxy group.
  • Examples of the “C2 to 6 alkenyloxy group” in R 7 include C2 to 6 alkenyloxy groups such as vinyloxy group, allyloxy group, propenyloxy group and butenyloxy group.
  • As the substituent on the "C1-6 alkoxy group”, “C1-6 alkylcarbonyloxy group” and “C2-6alkenyloxy group” in R 7 preferably a fluoro group, a chloro group, a bromo group, an iodo group and the like are used. Halogeno group; cyano group, C1-6 alkoxy group can be mentioned.
  • R 8 is a hydrogen atom.
  • R 7 and R 8 may be combined together to form a substituted or unsubstituted C1-6 alkoxyimino group.
  • Examples of the "C1 to 6 alkoxyimino group" formed by R 7 and R 8 together include a methoxyimino group and an ethoxyimino group.
  • a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group can be mentioned.
  • X is a halogeno group or a substituted or unsubstituted C1-6 alkoxy group.
  • halogeno group examples include a fluoro group, a chloro group, a bromo group, an iod group and the like.
  • substituted or unsubstituted C1 to 6 alkoxy groups examples include the same groups specifically exemplified in R 7 .
  • n is an integer of 0 to 5, and when n is 2 or more, X may be the same or different from each other.
  • Q is a group represented by formula (Q-1), formula (Q-2) or (Q-3).
  • R c and R d are independently hydrogen atoms, substituted or unsubstituted C1 to 6 alkyl groups, substituted or unsubstituted C1 to 6 alkoxy groups, substituted or unsubstituted.
  • a C3 to 8 cycloalkyl group, a substituted or unsubstituted 5-membered heterocyclyl group, or a group represented by the formula "-CR g N-OR h ".
  • R h is a substituted or unsubstituted C1 to 6 alkyl group.
  • R e and R f are independently hydrogen atoms or substituted or unsubstituted C1 to 6 alkyl groups.
  • R i is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group.
  • R c and R d examples include the same ones specifically exemplified in R 1 , and "substituted or unsubstituted C1 to 6 alkoxy groups". , The same as those specifically exemplified in R 7 can be mentioned.
  • Examples of the "C3-8 cycloalkyl group" in R c and R d include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cubicyl group and the like.
  • Preferred examples of the substituent on the "C3-8 cycloalkyl group" in R c and R d include a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; and a cyano group.
  • the "5-membered heterocyclyl group" in R c and R d includes 1 to 4 hetero atoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom as ring constituent atoms.
  • Examples of the "5-membered heterocyclyl group” include a 5-membered saturated heterocyclyl group, a 5-membered heteroaryl group, and a 5-membered partially unsaturated heterocyclyl group.
  • Examples of the 5-membered saturated heterocyclyl group include a pyrrolidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, an imidazolidinyl group, a pyrazolidinyl group, an oxazolidinyl group, an isooxazolidinyl group, a thiazolidinyl group and an isothiazolidinyl group. ..
  • Examples of the 5-membered heteroaryl group include a pyrrolyl group, a frill group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group. Can be done.
  • Examples of the 5-membered partially unsaturated heterocyclyl group include a pyrrolinyl group, a dihydrofuranyl group, a dihydrothiophenyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, an isooxazolinyl group, a thiazolinyl group and an isothiazolinyl group. ..
  • a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group
  • a methyl group, an ethyl group, an n-propyl group and an i- C1-6 alkyl groups such as propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group
  • difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group C1 to 6 haloalkyl groups such as; cyano group;
  • Examples of the "substituted or unsubstituted C1 to 6 alkyl groups" in R h include the same ones specifically exemplified in R 1 .
  • Examples of the "substituted or unsubstituted C1 to 6 alkyl groups" in R e and R f include the same ones specifically exemplified in R 1 .
  • the salt of compound (I) is not particularly limited as long as it is an horticulturally acceptable salt.
  • salts of inorganic acids such as hydrochloric acid and sulfuric acid
  • salts of organic acids such as acetic acid and lactic acid
  • salts of alkali metals such as lithium, sodium and potassium
  • salts of alkaline earth metals such as calcium and magnesium
  • iron, copper and the like Transition metal salts
  • salts of organic bases such as triethylamine, tributylamine, pyridine, hydrazine; ammonia and the like.
  • the method for producing the compound (I) or the salt of the compound (I) is not limited.
  • the compound (I) of the present invention or the salt of the compound (I) can be obtained by a known method as described in Examples and the like. Further, the salt of compound (I) can be obtained from compound (I) by a known method.
  • the agricultural and horticultural fungicide of the present invention contains at least one selected from the group consisting of compound (I) and a salt thereof as an active ingredient.
  • the amount of compound (I) or a salt thereof contained in the bactericidal agent for agriculture and horticulture of the present invention is not particularly limited as long as it exhibits a bactericidal effect.
  • the agricultural and horticultural fungi of the present invention include a wide variety of filamentous fungi, such as algae fungi (Oomycetes), ascomycetes (Ascomycetes), imperfect fungi (Deuteromycetes), basidiomycetes, and zygomycetes. It can be used to control plant diseases derived from fungi belonging to fungi (Zygomycetes).
  • Cercospora beticola black root disease (Aphanomyces cochlioides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris), rust (Uromyces betae), powdery mildew (Oidium sp.), Spots Diseases (Ramularia beticola), seedling blight (Aphanomyces cochlioides, Pythium ultimum), etc .
  • Peanuts brown spot (Mycosphaerella arachidis), plaque (Ascochyta sp.), Rust (Puccinia arachidis), blight (Pythium debaryanum), rust (Alternaria alternata), white silk (Sclerotium rolfsii) black Astringency (Mycosphaerella berkeleyi), etc .; Cucumber: Udonko disease (Sphaero
  • Tomatoes Botrytis cinerea, Cladosporium fulvum, Phytophthora infestans, Verticillium albo-atrum, Verticillium dahliae, powdery mildew (Oidium neolycopersici), powdery mildew (Alternaria) solani), powdery mildew (Pseudocercospora fuligena), etc .
  • Eggplant Botrytis cinerea, Corynespora melongenae, powdery mildew (Erysiphe cichoracearum), soot mold (Mycovellosiella nattrassii), sclerotinia sclerotiorum, Verticillium dah Brown spot disease (Phomopsis vexans), etc .
  • Strawberries Botrytis cinerea, powdery mildew (Sphaerotheca humuli), coll
  • Campestris black rot (Pseudomonas syringae pv. Maculicola, P. s. Pv. Alisalensis), downy mildew Diseases (Peronospora parasitica), sclerotinia sclerotiorum, black rot (Alternaria brassicicola), Botrytis cinerea, etc.; Green beans: Sclerotinia sclerotiorum, Botrytis cinerea, Colletotrichum lindemuthianum, Phaeoisariopsis griseola, etc.;
  • Apples Udonko disease (Podosphaera leucotricha), scab (Venturia inaequalis), Monilinia mali, black spot disease (Mycosphaerella pomi), rot disease (Valsa mali), spot deciduous disease (Alternaria mali), gymnosporangium yamadae), ring pattern disease (Botryosphaeria berengeriana), charcoal disease (Glomerella cingulata, Colletotrichum acutatum), brown spot disease (Diplocarpon mali), soot spot disease (Zygophiala jamaicensis), soot spot disease (Gloeodes pomigena), purple spot feather disease (Helicobasidium mompa), Botrytis cinerea, Erwinia amylovora, etc .; Plum: Cladosporium carpophilum, Botrytis cinerea, Monilinia mumecola, Peltaster sp., Etc.
  • Potatoes plague (Phytophthora infestans), summer plague (Alternaria solani), black blight (Thanatephorus cucumeris), half-body wilt (Verticillium albo-atrum, V. dahliae, V. nigrescens), black rot (Pectobacterium atrosepticum) Diseases (Pectobacterium carotovorum), etc .; Bananas: Panama disease (Fusarium oxysporum), black sigatoka disease (Mycosphaerella fijiensis, M.
  • the fungicide for agriculture and horticulture of the present invention is used for cereals; vegetables; root vegetables; potatoes; fruit trees, tea, coffee, cacao and other trees; pastures; turf; cotton and other plants. Is preferable.
  • the agricultural and horticultural fungicides of the present invention can be applied to various parts of plants, for example, leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, stems, roots, shoots, cuttings and the like. ..
  • improved varieties / varieties of these plants, cultivars, mutants, hybrids, and genetically modified organisms (GMOs) can also be targeted.
  • the fungicide for agricultural and horticultural use of the present invention is used for seed treatment, foliage spraying, soil application, water surface application, etc., which are performed to control various diseases occurring in agricultural and horticultural crops including flowers, turf, and grass. Can be done.
  • the agricultural and horticultural fungicide of the present invention may contain components other than the thienopyrimidine compound of the present invention.
  • other components include known carriers used for formulation.
  • conventionally known fungicides, insecticides / acaricides, nematode insecticides, soil pesticides, plant regulators, synergists, fertilizers, soil conditioners, animal feeds and the like can be mentioned. be able to. By containing such other components, a synergistic effect may be produced.
  • Nucleic acid biosynthesis inhibitor (A) RNA polymerase I inhibitor: Benalaxil, Benalaxil-M, Flaluxil, Metalaxil, Metalaxil-M; Oxadixil; Closilacon, Offrace; (B) Adenosine deaminase inhibitors: bupirimate, dimethilimol, etilimol; (C) DNA / RNA synthesis inhibitors: himexazole, octinenone; (D) DNA topoisomerase II inhibitor: oxolinic acid.
  • Mitotic and fission inhibitors (A) ⁇ -tubulin polymerization inhibitor: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate-methyl; dietofencarb; zoxamide; etaboxam; (B) Cell division inhibitor: pencyclon; (C) Inhibitor of spectrin-like protein delocalization: fluoricolide.
  • Respiratory inhibitor (A) Complex I-NADH Oxidoreductase Inhibitor: Diflumetrim; Torfenpyrad; (B) Complex II-succinate dehydrogenase inhibitors: benodanyl, flutranyl, mepronil; isofetamide; fluopirum; fenfurum, flumecyclox; carboxin, oxycarboxyne; tifluzamide; benzobindiflupill, bixaphen, fluxapiroki Sad, flametopil, isopyrazam, penflufen, penthiopyrado, sedaxan; boscalide, pidiflumethofen, isoflusifram, pyraziflumid, impylfurxam; (C) Complex III-ubiquinol oxidase Qo inhibitors: azoxystrobin, spumoxystrobin, kumethoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin,
  • Amino acid and protein synthesis inhibitors (A) Methionine biosynthesis inhibitors: andprim, cyprodinyl, mepanipyrim, pyrimethanyl; (B) Protein synthesis inhibitor: Blasticidin-S, casugamycin, casugamycin hydrochloride, streptomycin, oxytetracycline.
  • Signal transduction inhibitor (A) Signal transduction inhibitors: quinoxyphen, proquinazide; (B) MAP / histidine kinase inhibitors in osmotic signaling: fenpicronyl, fludioxonyl; clozolinate, iprodion, procymidone, vinclozoline.
  • Lipid and cell membrane synthesis inhibitor (A) Phospholipid biosynthesis, methyltransferase inhibitor: edifenephos, iprobenphos, pyrazophos; isoprothiolane; (B) Lipid oxidizers: biphenyl, chloroneb, dichloran, kinden, technazen, turquophosmethyl; etridiazole; (C) Agents acting on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb hosetylate, prothiocarb; (D) Pathogens Microorganisms that disrupt cell membranes: Bacillus subtilis, Bacillus subtilis QST713, Bacillus subtilis FZB24, Bacillus subtilis MBI600, Bacillus subtilis D747; (E) Agent that disturbs cell membranes: Extract of Gosei Kayupte (tea tree).
  • Cell membrane sterol biosynthesis inhibitor (A) Demethylation inhibitor at position C14 in sterol biosynthesis: trifoline; pyriphenox, pyrisoxazole; phenalimol, fluconazole, nuarimol; imazalyl, imazalyl sulfate, oxypoconazole, pefrazoate, prochloraz, fluconazole , Biniconazole; azaconazole, bitertanol, bromconazole, cyproconazole, diclobutrazole, diphenoconazole, diniconazole, diniconazole-M, epoxyconazole, etaconazole, fenbuconazole, fluconazole, fluconazole, fluconazole Fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole, fluconazole, flucon
  • Trehalase inhibitor validamycin
  • Chitin synthase inhibitors polyoxine, polyoxolim
  • C Cellulose Synthetic Enzyme Inhibitors: Dimethmorph, Fulmorph, Pyrimorph; Bench Avaricarb, Iprovaricarb, Variphenalate; Mandipropamide.
  • Melanin biosynthesis inhibitor (a) Melanin biosynthesis reductase inhibitor: fusalide; pyrokyron; tricyclazole; (B) Dehydrating enzyme inhibitor for melanin biosynthesis: calpropamide; diclosimet; phenoxanyl; (C) Inhibitor of melanin biosynthesis polyketide synthesis: toluprocarb.
  • Host plant resistance inducer (A) Agent acting on the salicylic acid synthesis pathway: acibenzolar-S-methyl; (B) Others: probenazole, thiazinyl, isothianil, diclobenazox, laminarin, Reynoutria sachalinensis extract.
  • Agents of unknown activity simoxanyl, Josetylaluminum, phosphate (phosphate), tecrophthalam, triazoxide, flusulfamide, dichromedin, metasulfocarb, ciflufenamide, metrafenone, pyriophenone, dodine, dodine free base, fluthianyl.
  • Agents having multiple points of action copper (copper salt), Bordeaux solution, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; ferbum, mancozeb, maneb, Mancopper, methylam, polycarbamate, propineb, tiram, dineb, dilam; captan, captahole, folpet; chlorotalonyl; diclofluanide, trillfluanide; guazatin, iminoctadine acetate, iminoctadine albesilate (iminoctadine) trialbesilate); anilazine; dithianone; quinomethionate; fluorimide.
  • insecticides / acaricides, nematodes, soil pesticides, anthelmintics, etc. that can be mixed or used in combination with the agricultural and horticultural fungicides of the present invention are shown below.
  • Acetylcholinesterase inhibitor (A) Carbamates: Aranicalb, Aldicarb, Bengiocarb, Benfracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiophenacarb, Phenoccarb, Formanate, Frathiocarb, Isoprocarb, Methiocarb, Methomyl, Oxamil, Pyrimicarb, Propoxyl, Thiodicarb, thiofanox, triazamate, trimetacarb, XMC, xylylcarb, phenothiocarb, MIMOC, MPMC, MTMC, aldicarb, alixicalve, aminocarb, butocarboxim, chlorocarb, metam sodium, promecarb;
  • GABA-operated chlorine ion channel antagonists acetoprol, chlordane, endosulfan, ethiprol, fipronil, pilafprowl, pyriprol, campechlor, heptachlor, dienochlor.
  • Nicotinic acetylcholine receptor agonists acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyradiflon.
  • Nicotinic acetylcholine receptor allosteric modulator spinetram, spinosad.
  • Chloride channel activator abamectin, emamectin benzoate, repimectin, milbemectin; ivermectin, selamectin, dramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime, nemadetin.
  • Juvenile hormone-like substances hydroprene, quinoprene, mesoprene, phenoxycarb, pyriproxyfen; diophenolan, epophenonan, triprene.
  • Other non-specific inhibitors methyl bromide, chloropicrin, sulfuryl fluoride, borax, liquor stone.
  • Diptera selective feeding inhibitors fronicamid, pimetrodin, pyrifluquinazone.
  • Tick growth inhibitors clofentezine, difluorovidazine, hexitiazox, etoxazole.
  • Microbial-derived insect mid-intestinal membrane-destroying agent Bacillus thuringiensis subspecies Isla Elenshi, Bacillus thuringiensis subspecies Isla Elenshi, Bacillus thuringensis subspecies Isawai, Bacillus thuringiensis subspecies Kurstaki, Bacillus thuringiensis subspecies Teneblionis, Bt Crop proteins (Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1).
  • Mitochondrial ATP biosynthetic enzyme inhibitor diafentiurone, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradiphon.
  • Oxidative phosphorylation decoupling agent chlorfenapyr, sulfamide, DNOC, binapacryl, dinobutone, dinocup.
  • Nicotinic Acetylcholine Receptor Channel Blocker Bensultap, Cartap Hydrochloride; Nelystoxin; Thiosultap Monosodium Salt, Thiocyclum.
  • Chitin synthesis inhibitors bistrifluron, chlorflubenzuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumron, lufenuron, novalron, nobiflumron, teflubenzuron, triflubenzuron, buprofezin, fluazuron.
  • Diptera molting disturber Cyromazine.
  • Moulting hormone receptor agonists chromaphenozide, halophenozide, methoxyphenozide, tebufenozide.
  • Octopamine receptor agonists Amitraz, Demiditraz, Chlordimeform.
  • Mitochondrial electron transport chain complex III inhibitor acequinosyl, fluacripirim, hydramethylnon.
  • Mitochondrial electron transport chain complex I inhibitor phenazakin, phenpyroximate, pyrimidiphen, pyridaben, tebufenpyrado, tolfenpyrad, rotenone.
  • Voltage-gated sodium channel blockers indoxacarb, metaflumisone.
  • Acetyl-CoA carboxylase inhibitor spirodiclophen, spiromesiphen, spirotetramato.
  • Mitochondrial electron transport chain complex IV inhibitor aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide.
  • Mitochondrial electron transport chain complex II inhibitor sienopyraphen, siflumethofen, pifrubmid.
  • Ryanodine receptor modulators chloranthraniliprole, cyantraniliprole, flubendiamide, cyclaniliprole, tetraniliprole.
  • Anthelmintic (A) Benzimidazole system: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, flubendazole; fevantel, netobimin, thiophanate; thiabendazole, cambendazole; (B) Salicylanilide system: closantel, oxyclozanide, lafoxanide, niclosamide; (C) Substituted phenolic system: nitroxynyl, nitroscanate; (D) Pyrimidines: Pyrantel, Morantel; (E) Imidazothiazole type: levamisole, tetramisole; (F) Tetrahydropyrimidines: Praziquantel, Epsiprantel; (G) Other anthelmintics: cyclodiene, liania, chlorthrone, metronidazole,
  • the agricultural and horticultural fungicide of the present invention is not particularly limited depending on the dosage form.
  • dosage forms such as wettable powders, emulsions, powders, granules, aqueous solvents, suspensions, granule wettable powders, and tablets can be mentioned.
  • the preparation method for the preparation is not particularly limited, and a known preparation method can be adopted depending on the dosage form.
  • (Formulation Example 6: Granule wettable powder) 40 parts of thienopyrimidine compound of the present invention, 36 parts of clay, 10 parts of potassium chloride, 1 part of sodium alkylbenzene sulfonic acid salt, 8 parts of sodium lignin sulfonic acid salt and 5 parts of formaldehyde condensate of sodium alkylbenzene sulfonic acid salt are uniformly mixed. After finely crushing, add an appropriate amount of water and knead to make it clay-like. The clay-like material is granulated and then dried to obtain a granule wettable powder containing 40% of the active ingredient.
  • the solvent was distilled off under reduced pressure, the obtained residue was dissolved in t-butyl alcohol (180 ml), cesium carbonate (39 g) was added, and the mixture was stirred at 80 ° C. for 5 hours.
  • the reaction mixture was concentrated, saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate.
  • the organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate.
  • the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: chloroform / ethyl acetate) to obtain 11.5 g of the target compound.
  • Step 2 Ethyl 1-(2- (5-fluoro-2-methoxyphenyl) -2-oxoethyl) -3- (3- (isopropylamino) -2,2-dimethyl-3-oxopropyl) -5-methyl-2,4-dioxo Synthesis of -1,2,3,4-tetrahydrothieno [2,3-d] pyrimidine-6-carboxylate
  • the obtained solid was dissolved in methylene chloride (250 ml), trifluoroacetic acid (25 ml) was added, and the mixture was stirred overnight at room temperature.
  • the reaction mixture was concentrated under reduced pressure, methylene chloride (230 ml), isopropylamine (12 g), triethylamine (11 g), 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinan.
  • 40 ml of -2,4,6-trioxide (50% ethyl acetate solution, about 1.7 mol / L) was added, and the mixture was stirred overnight at room temperature.
  • the reaction mixture was concentrated, a 2N HCl aqueous solution (50 ml) was added, the mixture was extracted with ethyl acetate, the organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate.
  • the solvent was evaporated under reduced pressure, the obtained residue was dissolved in tetrahydrofuran (250 ml), carbonyldiimidazole (6 g) was added, and the mixture was stirred at room temperature for 1 hour.
  • the reaction solution was added to water (250 ml) in which sodium borohydride (2.2 g) was dissolved, and the mixture was stirred overnight at room temperature.
  • the reaction mixture was filtered, the mother liquor was concentrated, the obtained residue was dissolved in ethanol (35 ml), pyridine (0.6 g) and methoxyamine hydrochloride (0.6 g) were added at 70 ° C., and the mixture was stirred for 10 minutes.
  • the 1 H-NMR of the obtained target product is shown below.
  • Ethyl 2-amino-4-methyl-5- (2H-1,2,3-triazol-2-yl) thiophene-3-carboxylate (4.64 g) was dissolved in dichloromethane (90 ml), and at room temperature, triphosgene (triphosgene) 1.86 g) was added. Triethylamine (5.59 g) was added dropwise to this solution under ice-cooling, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was ice-cooled again, tert-butyl 3-amino-2,2-dimethylpropanoate (3.20 g) was added, and the mixture was stirred overnight at room temperature.
  • the reaction mixture was poured into ice water, extracted with ethyl acetate, the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate.
  • the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 5.88 g of the target compound. Yield 58%
  • the 1 H-NMR of the obtained target product is shown below.
  • Step 4 3- (1- (2- (5-fluoro-2-methoxyphenyl) -2-oxoethyl) -5-methyl-2,4-dioxo-6- (2H-1,2,3-triazol-2-yl) Synthesis of -1,4-dihydrothieno [2,3-d] pyrimidin-3 (2H) -yl) -N-isopropyl-2,2-dimethylpropanamide
  • the reaction mixture was concentrated under reduced pressure, and the obtained residue was suspended in dichloromethane (30 ml), isopropylamine (1.22 g), N, N-diisopropylethylamine (2.66 g), O- (7-azabenzotriazole-).
  • 1-Il) -N, N, N', N'-tetramethyluronium hexafluorophosphate (3.92 g) was added, and the mixture was stirred overnight at room temperature.
  • the reaction mixture was concentrated under reduced pressure, poured into ice water, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous magnesium sulfate.
  • Step 5 3- (1- (2- (5-fluoro-2-methoxyphenyl) -2-hydroxyethyl) -5-methyl-2,4-dioxo-6- (2H-1,2,3-triazol-2-yl) Synthesis of -1,4-dihydrothieno [2,3-d] pyrimidin-3 (2H) -yl) -N-isopropyl-2,2-dimethylpropanamide
  • the reaction mixture was concentrated under reduced pressure, poured into ice water, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous magnesium sulfate.
  • the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 3.10 g of the target compound. Yield 89%
  • the 1 H-NMR of the obtained target product is shown below.
  • Step 6 3- (1- (2- (2-cyanoethoxy) -2- (5-fluoro-2-methoxyphenyl) ethyl) -5-methyl-2,4-dioxo-6- (2H-1,2,3-triazol) -2-yl) -1,4-dihydrothieno [2,3-d] pyrimidin-3 (2H) -yl) -Synthesis of N-isopropyl-2,2-dimethylpropanamide
  • the reaction mixture was poured into ice water, extracted with ethyl acetate, the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate.
  • the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.24 g of the target compound. Yield 91%
  • the 1 H-NMR of the obtained target product is shown below.
  • Tables 1 and 2 show some of the compounds of the present invention produced by the same method as in the above Examples. In the table, the physical properties, melting point (mp) or refractive index (n D ) of each compound are also shown.
  • the configuration E or Z in Table 1 indicates the geometric isomer of the oxime group in R 2 .
  • “E” indicates an E configuration
  • “Z” indicates a Z configuration
  • “E / Z” indicates that the compound is a mixture of compounds in both configurations.
  • Me indicates a methyl group
  • Et indicates an ethyl group
  • an arrow indicates a binding site.
  • the configuration E or Z in Table 2 indicates the geometric isomer of the oxime group.
  • E indicates an E configuration
  • Z indicates a Z configuration
  • E / Z indicates that the compound is a mixture of compounds in both configurations.
  • the control price was calculated by the following formula.
  • Control value (%) 100- ⁇ Ratio of lesion area in treated plot / Ratio of lesion area in untreated plot ⁇ ⁇ 100
  • the thienopyrimidine compounds of the present invention have a bactericidal effect, including compounds that could not be exemplified. It is a compound that does not cause phytotoxicity to plants and has little toxicity to humans, livestock and fish and has little impact on the environment, and is useful as a pesticide.

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Abstract

La présente invention concerne un composé 2,4-dioxo-1,4-dihydrothiénopyrimidine présentant une excellente activité bactéricide et une excellente innocuité, et pouvant être avantageusement synthétisé industriellement ; et un bactéricide agricole et horticole contenant ce dernier en tant que principe actif.　L'invention concerne un composé 2,4-dioxo-1,4-dihydrothiénopyrimidine représenté par la formule (I) ou un sel de celui-ci.　Dans la formule (I), R1 représente un groupe alkyle en C1-C6 substitué ou non substitué, et R2 représente un groupe alcoxycarbonyle en C1-C6 substitué ou non substitué, ou similaire. R3, R4, R5, et R6 représentent chacun indépendamment un atome d'hydrogène, ou un groupe alkyle en C1-C6 substitué ou non substitué, ou similaire. R7 représente un atome d'hydrogène ou un groupe hydroxyle, ou similaire, et R8 représente un atome d'hydrogène. X est un groupe halogéno, ou similaire. Q est un groupe représenté par la formule (Q-1), ou la formule (Q-2), ou similaire.
PCT/JP2020/023546 2019-06-17 2020-06-16 Composé 2,4-dioxo-1,4-dihydrothiénopyrimidine, bactéricide agricole et horticole Ceased WO2020255946A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013071169A1 (fr) * 2011-11-11 2013-05-16 Nimbus Apollo, Inc. Inhibiteurs de l'acc et utilisations associées
WO2015007451A1 (fr) * 2013-07-15 2015-01-22 Syngenta Participations Ag Dérivés hétérobicycliques microbiocides
WO2017091627A1 (fr) * 2015-11-25 2017-06-01 Gilead Apollo, Llc Compositions fongicides contenant des dérivés de 2,4-dioxo-1,4-dihydrothiéno[2,3-d] pyrimidine
WO2019031384A1 (fr) * 2017-08-07 2019-02-14 日本曹達株式会社 Composé de thiéno[2,3-d]pyrimidine-2,4-(1h,3h)dione tétrasubstitué en position 1, 3, 5 et 6, et bactéricide agricole ou horticole
WO2019065483A1 (fr) * 2017-09-26 2019-04-04 日本曹達株式会社 Composé de thiéno[2, 3-d]pyrimidine-2, 4(1h, 3h)dione tétrasubstitué en position 1, 3, 5 et 6, et bactéricide à usage agricole et horticole
WO2019107393A1 (fr) * 2017-11-30 2019-06-06 日本曹達株式会社 Composé de thiéno[2,3-d]pyrimidine-2,4(1h,3h)dione tétrasubstitué en position 1, 3, 5 et 6, et fongicide agricole et horticole

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013071169A1 (fr) * 2011-11-11 2013-05-16 Nimbus Apollo, Inc. Inhibiteurs de l'acc et utilisations associées
WO2015007451A1 (fr) * 2013-07-15 2015-01-22 Syngenta Participations Ag Dérivés hétérobicycliques microbiocides
WO2017091627A1 (fr) * 2015-11-25 2017-06-01 Gilead Apollo, Llc Compositions fongicides contenant des dérivés de 2,4-dioxo-1,4-dihydrothiéno[2,3-d] pyrimidine
WO2019031384A1 (fr) * 2017-08-07 2019-02-14 日本曹達株式会社 Composé de thiéno[2,3-d]pyrimidine-2,4-(1h,3h)dione tétrasubstitué en position 1, 3, 5 et 6, et bactéricide agricole ou horticole
WO2019065483A1 (fr) * 2017-09-26 2019-04-04 日本曹達株式会社 Composé de thiéno[2, 3-d]pyrimidine-2, 4(1h, 3h)dione tétrasubstitué en position 1, 3, 5 et 6, et bactéricide à usage agricole et horticole
WO2019107393A1 (fr) * 2017-11-30 2019-06-06 日本曹達株式会社 Composé de thiéno[2,3-d]pyrimidine-2,4(1h,3h)dione tétrasubstitué en position 1, 3, 5 et 6, et fongicide agricole et horticole

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