WO2019107393A1 - 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 - Google Patents

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 Download PDF

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WO2019107393A1
WO2019107393A1 PCT/JP2018/043724 JP2018043724W WO2019107393A1 WO 2019107393 A1 WO2019107393 A1 WO 2019107393A1 JP 2018043724 W JP2018043724 W JP 2018043724W WO 2019107393 A1 WO2019107393 A1 WO 2019107393A1
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group
substituted
unsubstituted
compound
formula
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PCT/JP2018/043724
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岩田　淳
頼人 ▲桑▼原
千尋 西野
博 佐野
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日本曹達株式会社
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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 1,3,5,6-tetrasubstituted thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione compounds and fungicides for agriculture and horticulture. More specifically, the present invention provides 1,3,5,6-tetra-substituted thieno [2,3-d] pyrimidine-2,4 (which has excellent bactericidal activity, safety, and industrially advantageous synthesis). The present invention relates to a 1H, 3H) dione compound and an agricultural and horticultural fungicide containing the same as an active ingredient.
  • Priority is claimed on Japanese Patent Application No. 2017-230445, filed Nov. 30, 2017, the content of which is incorporated herein by reference.
  • Patent Document 2 discloses a compound represented by Formula (B) and the like.
  • Patent Document 3 discloses a compound represented by Formula (C) and the like.
  • Patent Document 4 discloses a compound represented by Formula (D) and the like.
  • Patent Document 5 discloses a compound represented by Formula (E) and the like.
  • Patent Document 6 discloses a compound represented by Formula (F) and the like.
  • Patent Document 7 discloses agricultural and horticultural fungicide applications such as compounds represented by formula (F).
  • Patent Document 8 discloses a compound represented by Formula (G), and the like.
  • Patent Document 9 discloses a compound represented by Formula (H) and the like.
  • the object of the present invention is to provide 1,3,5,6-tetra-substituted thieno [2,3-d] pyrimidine-2,4 (1H, 1 (H), which is excellent in bactericidal activity, safety and industrially advantageous synthesis.
  • 3H A dione compound (hereinafter, sometimes referred to simply as a "thienopyrimidine compound”), and an agricultural and horticultural fungicide containing the same as an active ingredient.
  • R 1 is a substituted or unsubstituted C1-6 alkyl group
  • R 2 is a C1-6 alkoxycarbonyl group or a 5- to 6-membered heteroaryl group
  • R 3 is a substituted or unsubstituted C1-6 alkoxycarbonyl group, or a substituted or unsubstituted C1-6 alkylaminocarbonyl group
  • R 4 and R 4 ′ are each independently a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group
  • R 6 ' is a hydrogen atom
  • X is a halogeno group or a substituted or unsubstituted C1-6 alkoxy group
  • n represents the number of chemically acceptable X, and is an integer of 0 to 5, and when n is 2 or more, X may be the same or different from each other
  • R 6 represents It is a group represented by Q-1) or (1,
  • R a is a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group
  • R b is a hydrogen atom or a C 1-6 alkyl group
  • R a and R b are combined to form a substituted or unsubstituted 5- or 6-membered ring together with the carbon atom to which they are attached It is also good.
  • the thienopyrimidine compound of the present invention is excellent in bactericidal activity, has a certain effect, is excellent in safety, and can be advantageously synthesized industrially.
  • the fungicide for agricultural and horticultural use of the present invention has an excellent control effect, does not cause phytotoxicity on plants, and has less adverse effects on human beings and fishes and environment.
  • the thienopyrimidine compound of the present invention is a compound represented by the formula (I) (hereinafter sometimes referred to as compound (I)), or a salt of the compound (I).
  • the term “unsubstituted” means that it is only the parent group. When it is described only by the name of a mother core, it means “unsubstituted” unless otherwise noted.
  • the term “substituted” means that any hydrogen atom of the mother core group is substituted with a group having the same or a different structure as the mother nucleus.
  • the “substituent” is another group bonded to the mother core.
  • 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 the effects of the present invention are obtained.
  • the following groups can be mentioned as specific examples of the group that can be a "substituent”.
  • Halogeno groups such as fluoro, chloro, bromo and iodo; 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.
  • An 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 and the like;
  • Ethynyl group 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-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.
  • a C2-6 alkynyl group of A C 3-8 cycloalkyl group such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cubanyl group and the like; C 3-8 cycloalkenyl groups such as 2-cyclopropenyl group, 2-cyclopentenyl group, 3-cyclohexenyl group, 4-cyclooctenyl group;
  • a C 6-10 aryl group such as phenyl group and naphthyl group; 5-membered heteroaryl group such as pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group
  • Hydroxyl group An oxo 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 and the like; A C 2-6 alkenyloxy group such as a vinyloxy group, an allyloxy group, a propenyloxy group, a butenyloxy group; A C2-6 alkynyloxy group such as ethynyloxy group, propargyloxy group; A C 6-10 aryloxy group such as phenoxy group and naphthoxy group; 5- to 6-membered heteroaryloxy group such as thiazolyloxy group and pyridyloxy group;
  • a C 1-6 haloalkyl group such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group and the like; 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; A C3-6 halocycloalkyl group such as a 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; C
  • Aminocarbonyl group C1-6 alkylaminocarbonyl groups such as methylaminocarbonyl group, dimethylaminocarbonyl group, ethylaminocarbonyl group, i-propylaminocarbonyl group and the like; Imino C1-6 alkyl groups such as iminomethyl group, (1-imino) ethyl group, (1-imino) -n-propyl group; Hydroxyimino C1-6 alkyl groups such as hydroxyiminomethyl group, (1-hydroxyimino) ethyl group, (1-hydroxyimino) propyl group; C1-6 alkoxyimino C1-6 alkyl groups such as methoxyiminomethyl group, (1-methoxyimino) ethyl group, etc.
  • a C1-6 alkylthio group such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group and the like;
  • a C 1-6 haloalkylthio group such as trifluoromethylthio group, 2,2,2-trifluoroethylthio group;
  • a C2-6 alkenylthio group such as a vinylthio group and an allylthio group;
  • a C 2-6 alkynylthio group such as ethynylthio group, propargylthio group;
  • C1-6 alkylsulfinyl groups such as methylsulfinyl, ethylsulfinyl and t-butylsulfinyl;
  • Tri C 1-6 alkylsilyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group; TriC6-10 arylsilyl groups such as triphenylsilyl group; and the like can be mentioned.
  • any hydrogen atom in the substituent may be substituted with a group having a different structure.
  • C1-6 indicate that the number of carbon atoms of the group to be a mother nucleus is 1 to 6, and the like. The number of carbon atoms does not include the number of carbon atoms present in the substituent.
  • the ethoxybutyl group is classified into a C2 alkoxy C4 alkyl group because the group to be a mother nucleus is a butyl group and the substituent is an ethoxy group.
  • R 1 is a substituted or unsubstituted C1-6 alkyl group.
  • the “C1-6 alkyl group” in R 1 may be linear or branched.
  • the alkyl group methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group, t-butyl group And i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.
  • C1-6 alkyl group having a substituent” in R 1 include Fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 1-chloroethyl group, 2,2,2-trifluoro Ethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2,2,2-trifluoro-1 -Trifluoromethylethyl group, 1,1,1,3,3,3-hexafluoropropan-2-yl group, perfluoropropan-2-yl group, perfluorohexyl group, perchlorohexyl group, 2,4 , C 1-6 haloalkyl groups such as 6-trichlorohe
  • Hydroxy C 1-6 alkyl groups such as hydroxymethyl group, hydroxyethyl group; C1 to C4 such as methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, n-propoxymethyl group, i-propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group and the like 6 alkoxy C1-6 alkyl groups; C6-10 aryl C1-6 alkyl groups such as benzyl group, phenethyl group and the like; And C3-8 cycloalkyl C1-6 alkyl groups such as cyclopropylmethyl group, 2-cyclopropylethyl group, cyclopentylmethyl group, 2-cyclohexylethyl group, 2-cyclooctylethyl group and the like.
  • a halogeno group such as fluoro, chloro, bromo or iodo is preferably 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 and the like; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group and the like And C1-6 haloalkoxy groups; cyano groups;
  • R 1 is preferably a C1-6 alkyl group, more preferably a methyl group.
  • R 2 is a C1-6 alkoxycarbonyl group or a 5- to 6-membered heteroaryl group.
  • Examples of the "C1-6 alkoxycarbonyl group" in R 2 include methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group and the like. it can.
  • the “5 to 6-membered heteroaryl group” for R 2 is a pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group And 5-membered heteroaryl groups such as tetrazolyl group; and 6-membered heteroaryl groups such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group and triazinyl group.
  • R 2 is preferably a 5-membered heteroaryl group, more preferably a pyrazolyl group or a triazolyl group.
  • R 3 is a substituted or unsubstituted C1-6 alkoxycarbonyl group or a substituted or unsubstituted C1-6 alkylaminocarbonyl group.
  • Examples of the “C1-6 alkoxycarbonyl group” for R 3 include the same as those specifically exemplified for R 2 .
  • C1-6 alkylaminocarbonyl group examples include mono C1-6 alkylaminocarbonyl groups such as methylaminocarbonyl group, ethylaminocarbonyl group and i-propylaminocarbonyl group; dimethylaminocarbonyl group, diethylaminocarbonyl group And di C1-6 alkylamino carbonyl group such as;
  • substituent on the "C1-6 alkoxycarbonyl group” and “C1-6 alkylamino carbonyl group” in R 3 include halogeno groups such as fluoro, chloro, bromo and iodo groups. .
  • R 3 is preferably a C1-6 alkylaminocarbonyl group, more preferably a mono C1-6 alkylaminocarbonyl group, and particularly preferably an i-propylaminocarbonyl group.
  • R 4 and R 4 ′ are each independently a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
  • R 4 and R 4 ′ can be the same as those specifically exemplified for R 1 .
  • R 4 and R 4 ′ are preferably a hydrogen atom or a C1-6 alkyl group, and more preferably a hydrogen atom or a methyl group.
  • R 6 is a group represented by formula (Q-1) or (1,3-dioxoisoindolin-2-yl) oxy group.
  • R a is a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group
  • R b is hydrogen It is an atom, or a C1-6 alkyl group.
  • R a and R b may be combined to form a substituted or unsubstituted 5- or 6-membered ring together with the carbon atom to which they are attached.
  • the wavy line indicating the bond (NO undefined stero bond) between N (nitrogen atom) and O (oxygen atom) in formula (Q-1) is an E form or Z form or a group thereof by nitrogen carbon double bond Indicates that it is a mixture.
  • R a substituted or unsubstituted C1 ⁇ 6 alkyl group in R a may be cited the same as those as specifically illustrated in R 1.
  • substituent on the "C1-6 alkyl group" for R a preferably a halogeno group such as fluoro, chloro, bromo or iodo; methoxy, ethoxy, n-propoxy, i-propoxy, and C1-6 alkoxy groups such as n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and the like.
  • Examples of the “C3-6 cycloalkyl group” for R a include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, and cuvanyl group.
  • Preferred examples of the substituent on the "C3-6 cycloalkyl group" for R a include halogeno groups such as fluoro, chloro, bromo and iodo.
  • Examples of the "C1-6 alkyl group" for R b can be the same as those specifically exemplified for R 1 .
  • a 5- to 6-membered ring (hereinafter sometimes referred to as Y) formed by bonding of R a and R b together with the carbon atom to which they are bonded, a cyclopentane ring, a cyclohexane ring, a tetrahydrofuran ring Tetrahydropyran ring, dioxolane ring, dioxane ring and the like can be mentioned.
  • This 5- to 6-membered ring may have a substituent. Examples of the substituent on Y include a hydroxyl group and an alkoxy group.
  • any two substituents on Y may be formed together: methylenedioxy (-OCH 2 O-), ethylenedioxy (-OCH 2 CH 2 O-), tri It may be a C1-6 alkylenedioxy group such as a methylenedioxy group.
  • the group represented by formula (Q-1) is preferably any one of groups represented by formulas (Q-1-1) to (Q-1-9).
  • N nitrogen atom
  • O in the formulas (Q-1-1), (Q-1-3), (Q-1-4), and (Q-1-7) to (Q-1-9)
  • a wavy line indicating a bond (NO undefined stero bond) with an oxygen atom) indicates that it is an E form or a Z form or a mixture thereof by a nitrogen carbon double bond.
  • R 6 is preferably a group represented by formula (Q-1), and more preferably any one of groups represented by formulas (Q-1-1) to (Q-1-9). preferable.
  • R 6 ′ is a hydrogen atom.
  • X is a halogeno group or a substituted or unsubstituted C1-6 alkoxy group.
  • halogeno group examples include fluoro, chloro, bromo and iodo groups.
  • C1-6 alkoxy group methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group, Examples thereof include s-butoxy group, t-butoxy group, and i-hexyloxy group.
  • Preferred examples of the substituent on the "C1-6 alkoxy group" for X include halogeno groups such as fluoro, chloro, bromo and iodo.
  • X is preferably a halogeno group or a C1-6 alkoxy group, more preferably a fluoro group or a methoxy group.
  • n represents the number of chemically acceptable X, and is an integer of 0 to 5. When n is 2 or more, X may be the same or different.
  • N is preferably 0 to 2.
  • the salt of compound (I) is not particularly limited as long as it is an agronomically 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
  • salts of transition metals such as ammonia, triethylamine, tributylamine, pyridine, and salts of organic bases such as hydrazine.
  • the salt of compound (I) or compound (I) is not particularly limited depending on the method for producing it.
  • the salt of compound (I) can be obtained from compound (I) by a known method.
  • Compound (I) or a salt of Compound (I) of the present invention can be obtained by a known production method described in the Examples and the like.
  • R 2 , R 4 , R 4 ′ and R 6 have the same meaning as those in formula (I).
  • the fungicide for agriculture and horticulture of the present invention contains at least one selected from compound (I) and a salt thereof as an active ingredient.
  • the amount of compound (I) or a salt thereof contained in the agricultural and horticultural fungicide of the present invention is not particularly limited as long as it exhibits a bactericidal effect.
  • the agricultural and horticultural fungicides of the present invention may be conjugated to a wide variety of filamentous fungi such as, for example, Oomycetes, Ascomycetes, Deuteromycetes, Basidiomycetes, It can be used to control plant diseases derived from fungi belonging to the fungus (Zygomycetes).
  • Examples of plant diseases (pathogenic bacteria) to be controlled are shown below.
  • Sugar beet Brown spot disease (Cercospora beticola), black root disease (Aphanomyces cochlioides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris), rust (Uromyces betae), powdery mildew (Oidium sp.), Spots Disease (Ramularia beticola), seedling blight (Aphanomyces cochlioides, Pythium ultimum), etc.
  • Peaches brown spot (Mycosphaerella arachidis), stain (Ascochyta sp.), Rust (Puccinia arachis), rot (Pythium debaryanum), rust (Alternaria alternata), scab (Sclerotium rolfsii) black Astringent disease (Mycosphaerella berkeleyi) etc.
  • Cucumber powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), vine disease (Mycosphaerella melonis), scab disease (Fusarium oxysporum), sclerotis disease (Sclerotinia sclerotiorum), gray mold disease (Botrytis cinerea) Anthracnose (Colletotrichum orbiculare), scab (Cladosporium cucumerinum), brown spot (Corynespora cassiicola), seedling blight (Pythium debaryanum, Rhizoctonia solaniKuhn), homoposis root rot (Phomopsis sp.) Lechrymans) etc.
  • Tomato gray mold (Botrytis cinerea), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans), half-body wilt (Verticillium albo-atrum, Verticillium dahliae), powdery mildew (Oidium neolycopersici), ringworm (Alternaria) solani), mildew (Pseudocercospora fuligena) and so on.
  • Strawberry Botrytis cinerea, powdery mildew (Sphaerotheca humuli), anthracnose (Colletotrichum acutatum, Colletotrichum fragariae), plague (Phytophthoracactorum), soft rot (Rhizopus stolonifer), yellow rot (Fusarium oxysporum) Diseases (Verticillium dahliae) etc.
  • Cabbage clubroot (Plasmodiophora brassicae), soft rot (Erwinia carotovora), black rot (Xanthomonas campes rtis pv. Campestris), black spot blight (Pseudomonas syringaepv. Maculicola, P. s. Pv. Alisalensis), downy mildew (Peronospora parasitica), sclerotis disease (Sclerotinia sclerotiorum), black scab (Alternaria brassicicola), gray mold (Botrytis cinerea) and the like. Bean: Sclerotinia sclerotiorum, Botrytis cinerea, Colletotrichum lindemuthianum, Phaeoisariopsis griseola etc.
  • Ume scab (Cladosporium carpophilum), Botrytis cinerea (Botrytis cinerea), Heil's disease (Monilinia mumecola), sour spot disease (Pelaster sp.), Etc.
  • Oysters powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), scaly leaf disease (Cercospora kaki), round star disease (Mycosphaerella nawae), etc.
  • Hypton disease (Monilinia fructicola), scab (Cladosporium carpophilum), homoposis rot (Phomopsis sp.), Perforated bacterial disease (Xanthomonas campestris pv. Pruni), leaf rot (Taphrinadeformans), anthracnose (Colletotrichum gloeosporioides) )Such.
  • scab (Monilinia laxa), plague (Stigmina carpophila), scab (Cladosporium carpophilum), leaf blight (Polystigma rubrum), spotted leaf blight (Alternaria alternata), anthracnose (Colletotrichum gloeospoides) and the like.
  • Sweet cherry Aspergillus niger (Monilinia fructicola), anthracnose (Colletotrichum acutatum), black spot (Alternaria sp.), Juvenile mildew (Monilinia kusanoi), brown canker (Mycosphaerella cerasella) and the like.
  • Grapes gray mold (Botrytis cinerea), powdery mildew (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum acutatum), downy mildew (Plasmopara viticola), mildew (Elsinoe ampelina), brown spot (Pseudocercospora) vitis), black rot (Guignardia bidwellii), white rot (Coniella castaneicola), rust (Phakopsora ampelopsidis), white cotton swab (pathogenic bacteria unidentified) and the like.
  • Pear scab disease (Venturia nashicola), red star disease (Gymnosporangium asiaticum), black spot disease (Alternaria kikuchiana), ring blight disease (Botryosphaeria berengeriana), powdery mildew (Phyllactinia mali), blight blight (Phomopsis fukushii), brown spots Disease (Stemphylium vesicarium), anthracnose (Glomerella cingulata) and so on. Tea: Botrytis disease (Pestalotiopsis longiseta, P.
  • Anthracnose Colletotrichum theae-sinensis
  • Blight disease Exobasidium reticulatum
  • Citrus scab (Elsinoe fawcettii), blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), black spot (Diaporthe citri), scab (Xanthomonas campestris pv. Citri) Powdery mildew (Oidium sp.), Plague (Phytophthora citrophthora), anthracnose (Colletotrichum fioriniae) and the like.
  • Blast Pyricularia oryzae
  • sheath blight Rhizoctonia solani
  • idiot Gibberella fujikuroi
  • sesame leaf blight Cochliobolus miyabeanus
  • seedling blight Pythium graminicola
  • leaf blight Xanthomonas oryzae
  • Seedling blight Burkholderia plantarii
  • brown streak Acidovorax avenae
  • bactericidal Backholderia glumae
  • leaf blight Cercospora oryzae
  • rice scab Ustilaginoidea virens
  • brown rice Alternaria alternata
  • Curvularia intermedia Curvularia intermedia
  • belly black rice Alternaria padwickii
  • reddish rice Epicoccum purpurascens
  • Tobacco sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum), plague (Phytophthora nicotianae), etc.
  • Tulip Gray mold (Botrytis cinerea) etc.
  • Sunflower downy mildew (Plasmopara halstedii), sclerotiosis (Sclerotinia sclerotiorum), Botrytis cinerea (Botrytis cinerea) and the like.
  • Bentgrass snow blight (Sclerotinia borealis), large patch (Rhizoctonia solani), brown patch (Rhizoctonia solani), duller spot (Sclerotinia homoeocarpa), blast (Pyricularia sp.), Fire blight (Pythium aphanidermatum), Anthracnose (Colletotrichum graminicola) etc.
  • Orchardgrass powdery mildew (Erysiphe graminis) etc.
  • Soybean purpura (Cercospora kikuchii), downy mildew (Peronospora manshurica), stem blight (Phytophthora sojae), rust (Phakopsora pachyrhizi), sclerotis disease (Sclerotinia sclerotiorum), anthracnose (Colletotrichum truncatum), scab disease (Botrytis cinerea), black rot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. Sojae) and the like.
  • Potato plague (Phytophthora infestans), summer plague (Alternaria solani), black scab (Thanatephorus cucumeris), half body wilt (Verticillium albo-atrum, V. dahliae, V. nigrescens), black scab (Pectobacterium atrosepticum) Disease (Pectobacterium carotovorum) etc.
  • Banana Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, M. musicola) and the like.
  • Mango Anthracnose (Colletotrichum aenigma) etc.
  • Seed rape sclerotinia sclerotiorum, root blight (Phoma lingam), black spot (Alternaria brassicae), etc.
  • Coffee rust (Hemileia vastatrix), anthracnose (Colletotrichum coffeanum), brown eye disease (Cercospora coffeicola) and the like.
  • Sugar cane brown rust (Puccinia melanocephala) etc.
  • Corn scab (Gloeocercospora sorghi), rust (Puccinia sorghi), southern leaf rust (Puccinia polysora), panicle sickness (ustilago maydis), sesame leaf blight (Cochliobolus heterostrophus), sous disease (Setosphaeria turcica) and the like.
  • Cotton Seedling blight (Pythium sp.), Rust (Phakopsora gossypii), mildew (Mycosphaerella areola), anthracnose (Glomerella gossypii) and the like.
  • the fungicides for agricultural and horticultural use of the present invention are used on cereals, vegetables, root vegetables, potatoes, fruit trees, trees such as fruits, tea, coffee, cacao, grasses, grasses, grasses, cotton etc. Is preferred.
  • the fungicides for agricultural and horticultural use of the present invention can be applied to each part of plants, for example, leaves, stems, handles, flowers, buds, fruits, seeds, sprouts, roots, tubers, tubers, shoots, cuttings, etc. .
  • improved varieties and varieties, cultivars, mutants, hybrids and genetically modified organisms (GMOs) of these plants can also be targeted.
  • the fungicide for agricultural and horticultural use of the present invention is used for seed treatment, foliage application, soil application, water surface application, etc. which are carried out to control various diseases occurring in agricultural and horticultural crops including florets, turf and grass. Can.
  • the agricultural and horticultural fungicide of the present invention may contain components other than the thienopyrimidine compound of the present invention.
  • Other components may include known carriers used for formulation and the like.
  • conventionally known fungicides, insecticides / acaricides, nematocides, soil insecticides, plant regulators, synergists, fertilizers, soil conditioners, animal feed and the like can be mentioned. be able to. By including such other components, a synergistic effect may be exhibited.
  • Nucleic acid biosynthesis inhibitors (a) RNA polymerase I inhibitors: benalaxyl (benalaxyl), benalaxyl-M (benalaxyl-M), fulalaxyl (furalaxyl), metalaxyl (metalaxyl), metalaxyl-M (metalaxyl-M), oxadixyl (oxadixyl), clozilacon ), Off-race (ofurace); (b) Adenosine deaminase inhibitors: bupirimate, dimethirimol, ethyrimol (ethirimol); (c) DNA / RNA synthesis inhibitors: hymexazol, octilinone; (d) DNA topoisomerase II inhibitor: o
  • Mitotic proliferation inhibitors and cytostatics (a) ⁇ -tubulin polymerization inhibitor: benomyl (benomyl), carbendazim (carbendazim), chlorphenazole (chlorfenazole), fuberidazole (fuberidazole), thiabendazole (thiabendazole), thiophanate (thiophanate), thiophanate methyl (thiophanate-methyl) , Dietophencarb (diethofencarb), zoxamide (zoxamide), etaboxam (ethaboxam); (b) cell division inhibitors: penccuron; (c) Delocalized inhibitors of spectrin-like protein: fluopicolide.
  • Respiratory inhibitor (a) Complex I NADH oxidoreductase inhibitors: diflumetrim, tolfenpyrad; (b) Complex II succinate dehydrogenase inhibitors: benodanyl (benodanil), flutolanil (flutolanil), mepronil (mepronil), isofetamide (isofemid), fluopyram (fluopyram), fenfuram (fenfuram), flumecyclox (furmecyclox) Carboxin, Oxycarboxin, Thifluzamide, Benzovindiflupyr, Bixafen, Fluxapiroxad, Flamethopyr, Isopyrazam, Penflufen (penflufen), penthiopyrade (penthiopyrad), sedaxane (sedaxane), boscalid (boscalid), pyradiflumid (pyraziflumid), pydiflumethofen (pydiflu
  • Signal transduction inhibitors (a) Signal transduction inhibitors: quinoxyfen (quinoxyfen), proquinazid (proquinazid); (b) MAP and histidine kinase inhibitors in osmotic signaling: fenpiclonil, fludioxonil, chlozolinate, iprodione, procymidone, vinclozolin.
  • Lipid and cell membrane synthesis inhibitors (a) Phospholipid biosynthesis, methyl transferase inhibitor: Edifenphos (edifenphos), iprobenphos (iprobenfos), pyrazophos (pyrazophos), isoprothiolane (isoprothiolane); (b) Lipid peroxides: biphenyl (biphenyl), chloroneb (chloroneb), dichloran (dichloran), quintozene (quintozene), tecnazen (tecnazene), tolclofos methyl (tolclofos-methyl), etridiazole (etridiazole); (c) Agents that act on cell membranes: iodocarb (iodocarb), propamocarb (propamocarb), propamocarb hydrochloride (propamocarb-hydrochloride), propamocarb busetylate (propamocarb-
  • Sterol biosynthesis inhibitor of cell membrane (a) Demethylation inhibitors at position C14 in sterol biosynthesis: Triforine, pyrifenox, pyrisoxazole, phenarimol, fenarimol, flurprimidol, fluarimidol, nuarimol, Imazalil (imazalil), Imazalil sulfate (imazalil-sulphate), Oxpoconazole fumarate (oxpoconazole fumarate), Pefrazoate (pefurazoate), Prochloraz (prochloraz), Triflumizole (triflumizole), Viniconazole (viniconazole), Azaconazole azaconazole), bitertanol, bromuconazole (bromuconazole), cyproconazole (cyproconazole), diclobutrazol (diclobutrazol), difenoconazole (difenoconazole), diniconazole (dini)
  • Trehalase inhibitor validamycin
  • Chitin synthetase inhibitors polyoxins (polyoxins), polyoxorim (polyoxorim);
  • Cellulose synthetase inhibitors dimethomorph, flumorph, pyrimorph, benthiavalicarab-isopropyl, iprovaricarb, valifenalate, mandipropamide (mandipropamid ).
  • Host plant resistance inducer (a) Agents acting on the salicylic acid synthesis pathway: Acibenzolar-S-methyl (acibenzolar-S-methyl); (b) Others: probenazole (probenazole), thiazinyl (tiadinil), isotianil (isotianil), dichlobenizox (dichlobentiazox), laminarin (laminarin), extract of reedoutria sachalinensis.
  • shimoxanil (cymoxanil), fosetyl-aluminium, phosphoric acid (phosphate) (phosphoric acid (phosphate)), teclophthalam (teclofalam), triazoloxide (triazole), flusulfamide flusulfamide), diclomezine, methasulfocarb, cyflufenamide, metrafenone, pyriofenone, dodine, dodine free base, flutianil.
  • Agents having multiple action points copper (copper salt) (copper (copper salt)), Bordeaux solution (bordeaux mixture), copper hydroxide (copper hydroxide), copper naphthalate (copper naphthalate), copper oxide (copper oxide) , Copper oxychloride (copper oxychloride), copper sulfate (copper sulfate), sulfur (sulfur), sulfur product (sulfur product), calcium polysulfide (calcium polysulfide), ferbam (ferbam), mancozeb (mancozeb), maneb (maneb) , Mankapper (mancopper), methylam (metiram), polycarbamate (polycarbamate), propineb (propineb), thiram (thiram), zineb (zineb), ziram (ziram), captan (captan), captafol, phorpet (Folpet), chlorothalonil, dichlofluanid, tolylfluanid
  • DBEDC fluorophorpet (fluorofolpet), guazatine acetate, bis (8-quinolinolato) copper (II) (bis (8-quinolinolato) copper (II)), propamidine ( propamidine), chloropicrin (chloropicrin), cyprofuram, agrobacterium (agrobacterium), bethoxazine, diphenylamine, diphenylamine, methyl isothiocyanate (MITC) (methylisothiocyanate), mildeomycin, capsaicin (Capsaicin), cuflaneb (cufraneb), cyprosulfamide (cyprosulfamide), dazomet (dazomet), debacarb (debacarb), dichlorophen (dichlorophen), flumethover (flumetover), fosetyl calcium (fosetyl-calcium), fosetyl sodium (fosetyl sodium) -sodium
  • an insecticide / acaricide, a nematocide, a soil insecticide, a pesticide and the like which can be used in combination or in combination with the agricultural and horticultural fungicides of the present invention are shown below.
  • Acetylcholinesterase inhibitors (a) Carbamate system: alanical (alanycarb), aldicarb (aldicarb), bendiocarb (bendiocarb), benfuracarb (benfuracarb), butocarboxim (butocarboxim), butoxycarboxim (butoxycarboxim), carbaryl (carbaryl), carbofuran (carbofuran), Carbosulfan (carbosulfan), ethiophenecarb (ethiofencarb), fenobucarb (fenobucarb), formetanate (formetanate), furathiocarb (furathiocarb), isoprobu (isoprocarb), methiocarb (methiocarb), metho (methhomyl), oxamil (oximyl) ), Propoxur, thiodicarb, thiophanox, triazamate, triazamate, trimetha
  • GABA-agonizing chloride channel antagonist acetoprole, acetoprole, chlordane, endosulfan (endosulfan), ethyprole (ethiprole), fipronil (fipronil), pyrafluprole (pyrafluprole), pyriprole (pyriprole), Camphechlor, heptachlor, dienochlor.
  • Sodium channel modulators acrolinathrin (acrinathrin), d-cis-trans allethrin (d-cis-transallethrin), d-trans allethrin (d-trans allethrin), bifenthrin (bifenthrin), bioallethrin (bioallethrin), bioarethrin s-Cyclopentyl isomers (bioallethrin s-cyclopentyl isomer), bioresmethrin (bioresmethrin), cycloprothrin (cycloprothrin), cyfluthrin (cyfluthrin), beta-cyfluthrin ( ⁇ -cyfluthrin), cyhalothrin (cyhalothrin), lambda-cyhalothrin ( ⁇ -cyhalothrin) cyhalothrin), gamma-cyhalothrin ( ⁇ -cyl
  • Nicotinic acetylcholine receptor agonists acetamiprid (acetamiprid), clothianidin (clothianidin), dinotefuran (dinotefuran), imidacloprid (imidacloprid), nitenpyram (nitenpyram), nithiazine (nithiazine), tiacloprid, thiamethoxam thaam Sulfoxaflor (sulfoxaflor), nicotine (nicotine), flupyradifurone (flupyradifurone), flupyrimine (flupyrimine).
  • Nicotinic acetylcholine receptor allosteric modulators spinetoram, spinosad.
  • Chloride channel activators Abamectin (abamectin), emamectin benzoate (emamectin-benzoate), lepimectin (lepimectin), milbemectin, milvermectin, ivermectin, selamectin, doramectin, emurinomectin (Eprinomectin), moxidectin (moxidectin), milbemycin (milbemycin), milbemycin oxime (milbemycin oxime), nemadectin (nemadectin).
  • Juvenile hormone-like substances hydroprene (hydroprene), kinoprene (methoprene), methoprene (phenopycarb), pyriproxyfen (pyriproxyfen), diophenolan (diofenolan), epofenonane (epofenonane), triprene (triprene) ).
  • Other nonspecific inhibitors methyl bromide, chloropicrin, sulfuryl fluoride, borax, tartar emetic.
  • Homoptera order selective antifeedants flonicamid (flonicamid), pimetrozin (pymetrozine), pyrifluquinazon (pyrifluquinazon).
  • Acaride growth inhibitor clofenthezin (clofentezine), diflovidazine (diflovidazin), hexythiazox (hexythiazox), etoxazole (etoxazole).
  • Microorganisms-derived insect midgut inner membrane disrupting agents Bacillus thuringiensis subsp. Islaerensis (bacillus thuringiensis subsp. Israelensis), Bacillus sphaericus (bacillus sphaericus), Bacillus thuringiensis subsp. Eiswai (bacillus thuringiensis subsp. Aizawai) , Bacillus thuringiensis subsp.
  • Kurstaki Bacillus thuringiensis subsp. Kurstaki
  • Teneburionis Bacillus thuringiensis subsp. Tenebrionis
  • Bt crop proteins Cry1Ab, Cry1Ac, Cry1Fa, Cry1A. 105, Cry2Ab, Ab2 , Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1.
  • Mitochondrial ATP biosynthesis enzyme inhibitor diafenthiuron (diafenthiuron), azocyclotin (azocyclotin), cyhexatin (cyhexatin), fenbutatin oxide oxidized, propargite (propargite), tetradiphone (tetradifon).
  • Oxidative phosphorylation and uncoupling agent chlorfenapyr (chlorfenapyr), sulfluramide (sulfluramid), DNOC, binapacryl (binacapacryl), dinobuton (dinobuton), dinocap (dinocap).
  • Nicotinic acetylcholine receptor channel blocker bensultap, cartap hydrochloride, nereistoxin, thiosultap-sodium salt, thiocyclam.
  • Chitin synthesis inhibitors bistrifluron (bistrifluron), chlorfluazuron (chlorfluazuron), diflubenzuron (diflubenzuron), flucycloxuron (flucycloxuron), flufenoxuron (flufenoxuron), hexaflumuron (hexaflumuron), Rufenuron (lufenuron), novaluron (novaluron), noviflumuron (noviflumuron), teflubenzuron (teflubenzuron), triflumuron (triflumuron), buprofezin (buprofezin), fluazuron (fluazuron).
  • molt-disrupting agents cyromazine.
  • Molting hormone receptor agonist Chromafenozide (halofenozide), halofenozide (halofenozide), methoxyfenozide (methoxyfenozide), tebufenozide (tebufenozide).
  • Octopamine receptor agonists amitraz (amitraz), demiditraz (demiditraz), chlordimeform (chlordimeform).
  • Mitochondrial electron transport complex III inhibitor acequinocyl, fluacrypyrim, hydramethylnon.
  • Mitochondrial electron transport complex I inhibitor phenazaquin (fenazaquin), fenpyroximate, fenimidoxime, pyridadifen, pyridaben (pyridaben), tebufenpyrad (tebufenpyrad), tolfenpyrad (tolfenpyrad), rotenone (rotenone).
  • Voltage-gated sodium channel blockers indoxacarb, metaflumizone (metaflumizone).
  • Acetyl CoA carboxylase inhibitor spirodiclofen (spirodiclofen), spiromesifen (spiromesifen), spirotetramat.
  • Mitochondrial electron transport complex IV inhibitor aluminum phosphide, calcium phosphide, phosphine, phosphine, zinc phosphide, cyanide.
  • Mitochondrial electron transport complex II inhibitor sienopyraphen (cyenopyrafen), ciflumethophene (cyflumetofen), pyflubumide (pyflubumide).
  • Ryanodine receptor modulators chlorantraniliprole (chloroantraniliprole), cyanantraniliprole (cyantraniliprole), flubendiamide (flubendiamide), cyclaniliprol (cycliliprole), tetraniliprol (tetraniliprole).
  • Mixed Function Oxidase Inhibitor Compound Piperonyl butoxide.
  • Latrophin receptor agonist depsipeptide (depsipeptide), cyclic depsipeptide (cyclodepsipeptide), 24-membered cyclic depsipeptide (24 membered cyclodepsipeptide), emodepside (emodepside).
  • Antiparasitic agent (a) Benzimidazole: fenbendazole (fenbendazole), albendazole (albendazole), triclabendazole (triclabendazole), oxybendazole (oxibendazole), mebendazole (mebendazole), oxfendazole (oxfendazole), perbendazole ( parbendazole), flubendazole (flubendazole), febantel (febantel), netobimin (netobimin), thiophanate (thiophanate), thiabendazole (thiabendazole), cambendazole (cambendazole); (b) Salicylanilides: closantel, oxyclozanide, rafoxanide (rafoxanide), niclosamide (niclosamide); (c) Substituted phenolics: nitroxinil, nitroscanate; (d) Pyrimidines: pyrantel,
  • the agricultural and horticultural fungicides of the present invention are not particularly limited by the dosage form.
  • dosage forms such as wettable powders, emulsions, powders, granules, aqueous solutions, suspensions, water dispersible granules, tablets and the like can be mentioned.
  • the preparation method for the preparation is not particularly limited, and known preparation methods can be adopted depending on the dosage form.
  • Formulation Example 1 Wettable powder 40 parts of the thienopyrimidine compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfuric acid ester, and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and finely ground to obtain a wettable powder of 40% active ingredient .
  • Formulation Example 3 Granule 5 parts of the thienopyrimidine compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite and 7 parts of sodium alkyl sulfate are uniformly mixed and finely ground, and then the particle diameter is made 0.5 to 1.0 mm. Granulate to obtain granules of 5% active ingredient.
  • Formulation Example 4 Granules 5 parts of the thienopyrimidine compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctyl sulfosuccinate sodium salt and 1 part of potassium phosphate were uniformly mixed and pulverized. Water is added thereto and thoroughly mixed, and then granulated and dried to obtain granules of 5% active ingredient.
  • Step 1 2- (1- (2- (5-fluoro-2-methoxyphenyl) -2-oxoethyl) -5-methyl-2,4-dioxo-6- (2H-1,2,3-triazole) Synthesis of -2-yl) -1,4-dihydrothieno [2,3-d] pyrimidin-3 (2H) -yl) -N-isopropyl-2-methylpropanamide
  • N-isopropyl-2-methyl-2- (5-methyl-2,4-dioxo-6- (2H-1,2,3-triazol-2-yl) -1,4-dihydrothieno [2,3-d 0.56 g of pyrimidine-3 (2H) -yl) propanamide was dissolved in 10 ml of N, N-dimethylformamide. To this, under ice cooling, 0.62 g of potassium carbonate and 0.44 g of 2-bromo-5'-fluoro-2'-methoxyacetophenone were added, and the mixture was stirred overnight at room temperature. The resulting solution was poured into ice water and extracted with ethyl acetate. The organic phase was washed with water and then with brine.
  • Step 2 2- (1- (2- (5-fluoro-2-methoxyphenyl) -2-hydroxyethyl) -5-methyl-2,4-dioxo-6- (2H-1,2,3-) Synthesis of triazol-2-yl) -1,4-dihydrothieno [2,3-d] pyrimidin-3 (2H) -yl) -N-isopropyl-2-methylpropanamide
  • Step 3 2- (1- (2-((1,3-dioxoisoindoline-2-yl) oxy) -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) -N-isopropyl-2 Of 2-Methylpropanamide (Compound No. 1)
  • Step 4 2- (1- (2-((ethylideneamino) oxy) -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) -N-isopropyl-2-methylpropanamide (Compound No. 2) Synthesis
  • Table 1 shows some of the compounds of the present invention prepared in the same manner as in the above examples.
  • properties, melting point (mp) or refractive index (n D ) are shown together as physical properties of each compound.
  • the configuration E or Z in the table indicates a geometric isomer of the (alkylideneamino) oxy group. "E” indicates that it is in the E configuration, “Z” indicates that it is in the Z configuration, and “E / Z" indicates that the compound is a mixture of compounds in both configurations.
  • Control value (%) 100- ⁇ Lesion area rate in treated area / Lesion area rate in untreated area ⁇ ⁇ 100
  • Test Example 1 Apple Scab Control Test Water was added to emulsion (I) such that the concentration of the thienopyrimidine compound was 125 ppm, and dissolved to obtain a drug solution. Subsequently, the above drug solution was sprayed onto apple seedlings (variety "Obayashi", 3 to 4 leaf stage) grown in a pot for raising seedlings, and then air dried. This was inoculated with conidia of apple scab (Venturia inaequalis) (treatment section). As a control, apple seedlings which were not sprayed with the drug solution were inoculated in the same manner as described above (untreated zone). They were placed in a 20 ° C. wet room with 12 hours of light and dark repeated. Two weeks after inoculation, the leaves of the apple seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.
  • Example 2 Cucumber gray mold emulsion Emulsion (I) was added with water so that the concentration of the thienopyrimidine compound was 125 ppm, and dissolved to obtain a drug solution. Subsequently, the above drug solution was applied to cucumber seedlings (cultivar "ground” system, cotyledon stage) grown in a pot for raising seedlings, and then air dried. To this, a conidia suspension of Botrytis cinerea (Botrytis cinerea) was dropped and inoculated (treatment section). As a control, cucumber seedlings which were not sprayed with the drug solution were inoculated in the same manner as described above (untreated zone). They were placed in a 20 ° C. wet room. Four days after the inoculation, the leaves of the cucumber seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.
  • Botrytis cinerea Botrytis cinerea
  • a cucumber gray mildew control test was conducted on thienopyrimidine compounds having the compound numbers 2, 4, 7, 8 and 11. All compounds showed a control value of 75% or more.
  • Test Example 3 Wheat Powdery Mildew Control Test Water was added to Emulsion (I) such that the concentration of the thienopyrimidine compound was 125 ppm, and dissolved to obtain a drug solution. Subsequently, the above drug solution was applied to wheat seedlings (cultivar "Chihoku", 1 to 2 leaf stage) grown in a pot for raising seedlings, and then air dried. To this, conidia of wheat powdery mildew (Erysiphe graminis f. Sp. Tritici) were sprinkled and inoculated (treatment section). As a control, wheat seedlings which were not sprayed with the drug solution were inoculated in the same manner as described above (untreated zone). They were placed in a 20 ° C. greenhouse. The leaves of the wheat seedlings were visually observed on the day 6 days after the inoculation to determine the lesion area ratio, and the control value was calculated.
  • Emulsion (I) Emulsion (I) such that the concentration of the thien
  • the wheat powdery mildew control test was conducted on the thienopyrimidine compounds having the compound numbers 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and 12. All compounds showed a control value of 75% or more.
  • Test Example 4 Wheat Leaf Rust Control Test Water was added to the emulsion (I) so that the concentration of the thienopyrimidine compound was 125 ppm, and dissolved to obtain a drug solution. Subsequently, the above drug solution was applied to wheat seedlings (variety "Agriculture No. 61", 1-2 leaf stage) grown in a pot for raising seedlings, and then air-dried. To this, the summer spore of wheat rust fungus (Puccinia recondita) was sprinkled and inoculated (treatment section). As a control, wheat seedlings which were not sprayed with the drug solution were inoculated in the same manner as described above (untreated zone). They were placed in a 20 ° C. greenhouse. The leaves of the wheat seedlings were visually observed on the day after 12 days from the inoculation to determine the lesion area rate, and the control value was calculated.
  • a wheat leaf rust control test was conducted on thienopyrimidine compounds having the compound numbers 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and 12. All compounds showed a control value of 75% or more.
  • Test Example 5 Acute Toxicity Test of Daphnia magna 1,3,5,6-Tetrasubstituted Thieno [2,3-d] pyrimidine-2,4 (1H, 3H) dione Compound as N, N-Dimethyl Compound It was dissolved in formamide. This was added to water and mixed to obtain a harmful composition for controlling harmful organisms on water of a final concentration of 0.001 ⁇ g / L, 0.01 ⁇ g / L, 0.1 ⁇ g / L, and 1 ⁇ g / L. Ten Daphnia magna were exposed to the above-mentioned aquatic aquatic harmful biocidal control composition at about 20 ° C. for 48 hours. Next, the swimming inhibition rate of 10 Daphnia magna was measured. The half-effect concentration (EC 50 value) was calculated from the measured values by the drawing method.
  • the thienopyrimidine compounds of the present invention have bactericidal effects, including compounds that could not be exemplified, because those selected at random among the thienopyrimidine compounds of the present invention exert the effects as described above, It can be understood that the compound is a compound which does not cause any adverse effects on plants, and which is less harmful to humans and animals and affecting the environment.
  • the thienopyrimidine compound of the present invention is excellent in bactericidal activity, has a certain effect, is excellent in safety, and can be advantageously synthesized industrially.
  • An agricultural and horticultural fungicide containing the thienopyrimidine compound of the present invention as an active ingredient has an excellent control effect against plant diseases, does not cause phytotoxicity in plants, and is toxic to humans and animals and to the environment. Little impact.

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Abstract

L'invention concerne : des composés représentés par la formule (I) ou des sels de ceux-ci ; et un fongicide agricole et horticole contenant au moins un composé choisi parmi lesdits composés et leurs sels. Dans la formule (I), R1 représente un groupe alkyle en C1-6 ou similaire, R2 représente un groupe alcoxycarbonyle en C1-6 ou similaire, R3 représente un groupe alcoxycarbonyle en C1-6 ou similaire, R4 et R4' représentent chacun indépendamment un atome d'hydrogène, un groupe alkyle en C1-6, ou similaire, R6' représente un atome d'hydrogène, X représente un groupe halogène, un groupe alcoxy en C1-6, ou similaire, n représente le nombre de X chimiquement acceptables et est un nombre entier de 0 à 5, les X peuvent être identiques ou différents lorsque n est égal à 2 ou plus, et R6 représente un groupe représenté par la formule (Q-1) ou similaire. Dans la formule (Q-1), * est une position de liaison, Ra est un groupe alkyle en C1-6 ou similaire, Rb est un atome d'hydrogène, un groupe alkyle en C1-6, ou similaire, et Ra et Rb peuvent se lier pour former un cycle de 5 à 6 chaînons substitué ou non substitué par des atomes de carbone auxquels Ra et Rb sont liés.
PCT/JP2018/043724 2017-11-30 2018-11-28 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 WO2019107393A1 (fr)

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WO2022230804A1 (fr) * 2021-04-28 2022-11-03 日本曹達株式会社 Composition fongicide agricole et horticole

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