CN115088722B - Application, method and composition of diphenyl ether compound containing triazole structure in preventing and controlling plant diseases - Google Patents

Application, method and composition of diphenyl ether compound containing triazole structure in preventing and controlling plant diseases Download PDF

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CN115088722B
CN115088722B CN202210960968.3A CN202210960968A CN115088722B CN 115088722 B CN115088722 B CN 115088722B CN 202210960968 A CN202210960968 A CN 202210960968A CN 115088722 B CN115088722 B CN 115088722B
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compound
plant diseases
rot
reaction
formula
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CN115088722A (en
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葛家成
胡堂路
李丽
邱佳鹏
邢阳阳
孙鹏
张亚弢
吕心童
杨志鹏
王玉
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Hailir Pesticides and Chemicals Group 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G13/00—Protecting plants
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Toxicology (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention belongs to the field of pesticides, and in particular relates to application, a using method and a composition of a diphenyl ether compound containing a triazole structure, wherein the compound has a structure shown in a formula (I):

Description

Application, method and composition of diphenyl ether compound containing triazole structure in preventing and controlling plant diseases
Technical Field
The invention belongs to the technical field of pesticides, and particularly relates to application, a method and a composition of a diphenyl ether compound containing a triazole structure in preventing and controlling plant diseases.
Background
Triazole bactericides have been developed in the last 60 th century and have been the only important place in the field of agricultural bactericides. With the 21 st century, the pesticide industry has been greatly changed, and the pesticide composition is efficient, low in toxicity and environment-friendly. And people pay more attention to environmental protection. Scientists are continually required to create new pesticides to replace the old pesticides that develop resistance. The 1- [ 2-chloro-4- (4-chlorophenoxy) phenyl ] -2- (1H- [1,2,4] triazole) -1-methyl ketone compound (I-1) referred to in the present invention is reported in both CN103648281B, CN103717578B, CN103732581B, CN103748082B and J.Agric.food chem (2009) 57, and the 1- [ 2-trifluoromethyl-4- (4-chlorophenoxy) phenyl ] -2- (1H- [1,2,4] triazole) -1-methyl ketone compound (I-2) is also referred to in CN103639057B, CN105152899B but is used as an intermediate only in the synthesis.
Disclosure of Invention
In order to solve the above problems in the prior art, the present invention provides an application of 2- (1H- [1,2,4] triazole) -1-methyl ketone compound, and the applicant surprisingly found that the 2- (1H- [1,2,4] triazole) -1-methyl ketone compound has higher bactericidal activity and broad spectrum than the known compounds as a pesticide acceptable salt, has outstanding biological activity on rust, powdery mildew, ring rot and brown rot, and has relatively better selectivity and crop safety.
The technical scheme adopted by the invention for achieving the purpose is as follows: the utility of diphenyl ether compound containing triazole structure for preventing and controlling plant diseases has the structural formula shown in formula (I):
In formula (I), R 1 is selected from H, CN, halogen, C 1-C6 alkyl, halogenated C 1-C6 alkyl, C 1-C6 alkoxy, halogenated C 1-C6 alkoxy, or C 3-C6 cycloalkyl.
Further, in formula (I), R 1 is selected from CN、F、Cl、Br、Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、CF3、CBr3、CCl3、CH2F、CH2Cl、CH2Br、CHF2、CHCl2、CHBr2、CH2CF3、CH2CBr3、CH2CCl3、CH2CH2F、CH2CH2Cl、CH2CH2Br、CH2CHF2、CH2CHCl2、CH2CHBr2、 methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, cyclopropane, cyclopentane or cyclohexane.
Further, in formula (I), R 1 is selected from CN、F、Cl、Br、Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、CF3、CBr3、CCl3、CH2F、CH2Cl、CH2Br、CHF2、CHCl2、CHBr2、CH2CF3、CH2CBr3、CH2CCl3、CH2CH2F、CH2CH2Cl、CH2CH2Br、CH2CHF2、CH2CHCl2、CH2CHBr2、 methoxy or ethoxy;
Still further, R 1 is selected from Cl or CF 3.
Further, the plant diseases include plant diseases caused by pathogenic bacteria of ascomycota, basidiomycota or deuteromycota.
Further, the pathogenic bacteria of ascomycota, basidiomycota or phylum half-known bacteria include Alternaria alternata, cellosporium, cercospora, brevibacterium, cephalosporium spinosum, tribulus terrestris, leptosporum, verticillium, cephalosporium, alternaria, cercospora, alternaria, leptosporum.
Further, the plant diseases include rust disease, powdery mildew, ring rot, brown rot;
further, the plant diseases include corn rust, soybean rust, wheat powdery mildew, apple ring rot, and peach brown rot.
The invention also discloses a bactericidal composition for preventing or controlling plant diseases, which comprises a biological effective amount of at least one of the compounds of the formula (I);
Further, a formulation carrier or formulation aid is included.
Also disclosed is a method of controlling or managing plant diseases comprising applying a biologically effective amount of at least one of the compounds of formula (I) as described above or a fungicidal composition as described above to a plant, plant propagation material or plant organ and cultivation medium, cultivation material or cultivation space which subsequently grows.
Further, the plant comprises a food crop or a commercial crop.
Further, the food crop comprises soybean, corn or wheat; the commercial crops comprise apple trees or peach trees.
In the definition of the structural formula of the above compounds, the terms used have the following meanings:
halogen or halogen: refers to fluorine, chlorine, bromine and iodine.
C 1-C6 alkyl: straight or branched alkyl groups having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl or n-butyl, isobutyl, sec-butyl, tert-butyl and the like.
Halogenated C 1-C6 alkyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, and hydrogen atoms on these alkyl groups may be partially or entirely substituted with halogen, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl and the like.
C 1-C6 alkoxy: a straight or branched alkyl group having 1 to 6 carbon atoms is bonded to the structure through an oxygen atom bond.
Halogenated C 1-C6 alkoxy: straight-chain or branched alkoxy groups having 1 to 6 carbon atoms, and hydrogen atoms on these alkoxy groups may be partially or entirely substituted with halogen, for example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy and the like.
The synthesis method of the compound shown in the formula I comprises the steps of reacting a compound shown in the formula IV with parachlorophenol (in the chemical formulas listed below, substituents and symbols have the same meaning as those defined in the formula I unless otherwise defined), obtaining a compound shown in the formula III, preparing a compound shown in the formula II from the compound shown in the formula III, and reacting the compound shown in the formula II with triazole to obtain the compound shown in the formula I.
Further, the reaction may be carried out at normal pressure or high pressure, preferably at atmospheric pressure, and the post-treatment may be carried out according to a conventional method.
Further, the solvent is selected from one or more of dichloromethane, toluene, DMF, DMSO, xylene, 1, 2-dichloroethane, tetrahydrofuran, methanol, ethanol, isopropanol.
Further, the reaction temperature is-50 to 150 ℃, preferably-10 to 100 ℃.
Further, the alkali is selected from one or more of potassium tert-butoxide, sodium tert-butoxide, potassium carbonate, sodium hydroxide, potassium hydroxide, N-dimethylformamide, pyridine, triethylamine, DMAP, DIPEA or sodium hydride.
The compounds of formula (I) and their fungicidal compositions of the present invention are suitable as plant fungicides, having biological activity against a wide range of phytopathogenic fungi, including, but not limited to, phylum plasmodiophora (Plasmodiophoromycota), oomyceta (oomyceta), phylum chytrium (Chytridiomycota), phylum zygomycota (Zygomycota), phylum ascomycota (Ascomycota), phylum basidiomycetes (Basidiomycota) and phylum half-known (Deuteromycota); the compound shown in the formula (I) and the bactericidal composition thereof can be used as foliar fungicides, seed dressing fungicides and soil fungicides for plant protection and can also be used for preventing or controlling harmful fungi of wood or plant roots.
The compound shown in the formula (I) and the bactericidal composition thereof can be used for preventing or controlling plant diseases including but not limited to the following diseases:
white rust (Albugo) on ornamental plants, vegetables (e.g., white rust (a. Candida)) and sunflowers (e.g., salomum senkyani white rust (a. Tragosporins)); vegetables, rape (brassica Alternaria (a. Brassicla) or brassica Alternaria (a. Brassicae)), sugar beet (a. Tenuis), fruit, rice, soybean, potato (e.g. Alternaria alternifolia (a. Solani) or Alternaria (a. Alternata)), tomato (e.g. Alternaria or Alternaria) and Alternaria (Alternaria leaf spot) on wheat; Sericin on sugar beet and vegetables (Aphanomyces); aschersonia (Ascochyta) on cereals and vegetables, such as a. Tritici (anthracnose) on wheat and aschersonia (a. Hordei) on barley; the genera Helminthosporium (Bipolaris) and Helminthosporium (Drechslera) (sexual: leptosporium (Cochliobolus)), such as leaf spot on corn (corn Helminthosporium (D. Maydis) or corn isolated Helminthosporium (B. Zeicola)), such as spot blight on cereals (Rhizoctonia cerealis (B. Sorokiniana), such as rice and grass (B. Oryzae); Powdery mildew (powdery mildew) of wheat (Blumeria (old name: erysiphe) on cereals (e.g., wheat or barley); fruit and berries (e.g., strawberries), vegetables (e.g., lettuce, carrots, root celery and cabbage), oilseed rape, flowers, vines, botrytis cinerea (sexual: botrytis cinerea (Botryotinia fuckeliana): botrytis cinerea) on forest plants and wheat; bremia lactucae (downy mildew) on lettuce; Long coracoid genus (Ceratocystis) (synonymous line mouth genus (Ophiostoma)) on broad-leaved and evergreen trees (rot or wilt), e.g., elm wilt (c ulmi) on elm (elm in the netherlands); corn (e.g., gray leaf spot: zebra corn (c.zeae-maydis)), rice, sugar beet (e.g., beet cercospora (c.beticola)), sugar cane, vegetables, coffee, soybeans (e.g., soybean gray leaf spot (c.sojina) or soybean purple leaf spot (c.kikuchi)), and cercospora (Cercospora) on rice (cercospora leaf spot); Tomato (e.g., tomato leaf mold (C.fulvum)) and cladosporium (Cladosporium) on cereals (e.g., cladosporium cucumerinum (C.herbarum) on wheat); ergot (CLAVICEPS PURPUREA) on cereals (ergot disease); corn (Gray Helminthosporium (C. Carbonum)), cereals (e.g., helminthosporium gramineum (C. Sativus)), asexual: helminthosporium gramineum) and rice (e.g., helminthosporium palustris (C. Miyabeam), asexual: helminthosporium (H. Oryzae)), helminthosporium (Helminthosporium) or Helminthosporium (leaf spot); Colletotrichum (Colletotrichum) (sexual: periclase (Glomerella)) (anthracnose) on cotton (e.g., colletotrichum gossypii), corn (e.g., colletotrichum graminearum (c. Graminicola))), berries, potatoes (e.g., colletotrichum citrulli (c. Coccodes))), beans (e.g., colletotrichum phaseoli (c. Lindemuthinum)) and soybeans (e.g., colletotrichum soja (c. Trunk) or Colletotrichum falcatum (c. Gloeosporides)); the genus Phanerochaete (Corticium), such as the genus Phanerochaete (C.sasakii) on rice (sheath blight); cucumber brown spot bacteria (Corynespora cassiicola) (leaf spot) on soybean and ornamental plants; leptospira (Cycloconium), such as C.oleaginum on olive trees; fruit trees, grape vine (e.g., C.liriodendri, sexual form: neonectria liriodendri: ustilago) and ginseng septoria (Cylindrocarpon) on ornamental trees (e.g., fruit rot or grape vine Ustilago, sexual form: conyza (Nectria) or aryporopsis (Neonectria)); Alternaria alternata (Dematophora (sexual: rosellinia) necatrix) (root rot/stem rot) on soybeans; north stem ulcer bacteria (Diaporthe) such as North stem ulcer bacteria (D.phaseolorum) on soybean (Rhizoctonia solani); corn, cereals such as barley (e.g., barley Leptosporum (D. Teres), leptosporum (R. Ternum)), and wheat (e.g., D. Tritici-repentis: brown spot), rice, and the genus Leptosporum on lawns (synonymous Helminthosporum, sexual: nuclear bacteria (Pyrenophora)); Escat (Esca) on grape vine (grape vine blight, dry rot) caused by Phaeopodium maculatum (Formitiporia (synonym Phellinus) pubstata), F.mediaterranea, phaeomoniella chlamydospora (old name Phaeoacremoniumchlamydosporum), phaeoacremonium aleophilum and/or Pubescentis (Botryosphaeriaobtusa); Elsinoe (E.pyri), berries (raspberry Elsinoe ampelina (E.veneta): anthracnose) and grapevine (grape Elsinoe (E.ampelina): anthracnose), elsinoe (Elsinoe); black powder (Entyloma oryzae) of rice leaf on rice (leaf smut); fucus (Epicoccum) on wheat (smut); sugar beet (beet powdery mildew (e.betae)), vegetables (e.g. pea powdery mildew (e.pisi)) such as powdery mildew (Erysiphe (e.g. Erysiphe necator), cabbage, and rape (e.g. e.cruciferae) on cucurbitaceae plants (Erysiphe); Side-bending spore bacteria (Eutypa lata) on fruit trees, grape vines and ornamental trees (Eutypa canker or wilt, asexual: cytosporina lata, synonym Libertellablepharis); the genus Helminthosporium (Exserohilum) (synonymous Helminthosporium) on corn (e.g., helminthosporium (E. Turcicum)); Fusarium (Fusarium) (sexual: gibberella (Gibberella)) (Fusarium, root rot, or stem rot) on various plants, such as Fusarium graminearum (F. Graminearum) or Fusarium culmorum (F. Culmorum), fusarium oxysporum (F. Oxysporum) on tomatoes, fusarium solani (F. Solani) on soybeans (f. Sp. Glycines), the current synonyms being North America soybean sudden death syndrome (F. Virgine) and Fusarium verticillium (F. Verisimilides) on corn, each causing sudden death syndrome; Top hulls (Gaeumannomyces graminis) on cereals (e.g., wheat or barley) and corn (take-all); gibberella on cereals (e.g. gibberella zeae (g. Zeae)) and rice (e.g. gibberella vinifera (g. Fujikuroi): bakanae); apple anthracnose (Glomerella cingulata) on grape vine, pome fruit and other plants, cotton anthracnose (g gossypii) on cotton; GRAINSTAINING COMPLEX on rice; black rot of grape (Guignardia bidwellii) on grape vine; Rust genus (Gymnosporangium) on rosaceous plants and juniper, such as g.sabinae (rust disease) on pear; the genus Helminthosporium (synonymous Neurospora, sexual: leptosporium) on corn, cereals and rice; camellias (heileia), such as camellias (h.castatrix) on coffee (brown leaf rust); isaria brown spot on grape vine (Isariopsis clavispora) (synonym Cladosporium vitis); aschersonia phaseoloides (Macrophomina phaseolina (synonym phaseoli)) on soybeans and cotton (root rot/stem rot); The plant species are selected from the group consisting of snow mold leaf mold (Microdochium (synonymous Fusarium) nivale (snow mold) on cereals such as wheat or barley, diffuse cross-hair shells (Microsphaera diffusa) on soybeans (powdery mildew), conidia (Monilinia), such as sclerotium rolfsii (m.laxa) on stone fruits and other rosaceous plants, peach brown rot (m.fructiola) and m.fructigena (flower rot and branch rot, brown rot), spherical cavity bacteria (mycosphaela) on cereals, bananas, berries and peanuts, such as m.graminicola (asexual: septoria (Septoria tritica), septoria (Sigatoka) on cereals, bananas; Cabbage (e.g. brassica napus (p. Brassicae)), rape (e.g. downy mildew (p. Paramedica)), onion (e.g. downy mildew (p. Destruxer)), tobacco (p. Tabacina)), and downy mildew (Peronospora) (downy mildew) on soybeans (e.g. downy mildew (p. Manshurica)). Pachyrhizus (Phakopsorapachyrhizi) and mountain Ma Huang (p.meibomiae) on soybeans (soybean rust); For example, genus Phycomycetes (Phialophora) on grape vine (e.g., P.trachila and P.tetraspora) and soybean (e.g., brown rot of soybean stem (P.gregata): stem disease); phoma tibioflavus (Phoma lingam) on rape and cabbage (root rot and stem rot) and phoma betatobrazil (P.betae) on sugar beet (root rot, leaf spot and pyocutaneous disease); phomopsis (Phomopsis) on sunflower, grape vine (e.g., black rot (p. Vintics) vines and leaf spot) and soybean (e.g., stem rot: p. Phaseoli, sexual: phomopsis sojae (Diaporthe phaseolorum)); Brown spot germ (Physoderma maydis) on corn (brown spot); various plants such as bell peppers and cucurbitaceae (e.g., phytophthora capsici (p.capsici)), soybean (e.g., phytophthora sojae), synonyms p.sojae, potatoes and tomatoes (e.g., phytophthora infestans (p.infestans): late blight) and Phytophthora (fusarium, root rot, leaf rot, stem rot and fruit tree rot) on broad-leaved trees (e.g., oak sudden death bacteria (p.ramorum): oak sudden death disease); Brassica cluba (Plasmodiophora brassicae) (clubroot) on cabbages, oilseed rape, radishes and other plants; peronospora (Plasmopara), such as Plasmodium viticola (P.viticola) on grape vine and Holstedii (P.halsetedii) on sunflower; the genus Desmodium (Podosphaera) (powdery mildew) on plants of the Rosaceae family, hops, pomegranates and berries, such as Malus pumila powdery mildew (P.leucotrichia) on apples; for example, polymyxa (Polymyxa) on cereals such as barley and wheat (p. Graminas) and sugar beet (p. Betae) and viral diseases transmitted thereby; wheat basal rot (Pseudocercosporella herpotrichoides) on cereals such as wheat or barley (eye spot, sexual form: tapesia yallundae); pseudoperonospora (downy mildew) on various plants, such as Pseudoperonospora cubensis (p. Cube) on cucurbitaceae or humulus scandens (p. Humili) on hops; pseudopeziculatracheiphila on grape vine (grape angular leaf spot pathogen or 'rotbrenner', asexual: phycomyces (Phialophora)); Puccinia (rust) on various plants, such as Puccinia (p.triccina) (brown rust or leaf rust) on cereals such as wheat, barley or rye, puccinia (p.striiformis) (stripe or yellow rust), puccinia (p.hordei) (barley yellow dwarf leaf rust), puccinia (p.graminis) (stem rot or black rust) or Puccinia (p.recondita) (brown rust or leaf rust), p.kuehnii (orange rust) on sugarcane and Puccinia (p.asparagi) on asparagus; Wheat yellow spot virus (Pyrenophora (asexual: drechslera) tritici-repentis) on wheat (maculopathy) or barley yellow spot internal navel vermicularia (P.teres) on barley (yellow spot); pyricularia species (Pyricularia), such as Pyricularia oryzae (P.oryzae) on rice (idiotype: magnaporthe grisea, pyricularia oryzae) and Pyricularia oryzae (P.grisea) on lawns and cereals; pythium (damping off) on lawns, rice, maize, wheat, cotton, rape, sunflower, soybean, sugar beet, vegetables and various other plants, such as Pythium terminalis (p. Ultamum) or Pythium aphanidermatum (p. Aphanidermatum); Genus post-partum (Ramularia), such as r.collo-cygni (post-partum leaf spot, physiological leaf spot) on barley and beet leaf spot bacteria (r.betiola) on sugar beet; rhizoctonia (Rhizoctonia) on cotton, rice, potato, turf, corn, canola, potato, sugar beet, vegetables, and various other plants, such as Rhizoctonia solani (r.solani) on soybean (root rot/stem rot), r.solani (sheath blight) on rice or Rhizoctonia cerealis (r.cerealis) on wheat or barley (wheat sheath blight); Rhizopus (Rhizopus stolonifer) on strawberries, carrots, cabbages, vines and tomatoes (black mold, soft rot); ryegrass (Rhynchosporium secalis) (leaf spot) on barley, rye, and triticale; branch (Sarocladium oryzae) and S.attenuum (leaf sheath rot) on rice; sclerotinia (sclerotiorum) on vegetables and field crops such as rape, sunflower (e.g. Sclerotinia (s. Sclerotiorum)) and soybean (e.g. s. Rolfsii or Sclerotinia (s. Sclerotiorum)); septoria (Septoria) on various plants, such as Septoria sojae (s.glycons) on soybean (brown spot), septoria tritici (s.tritici) on wheat (Septoria leaf spot) and Septoria nodorum (s. (synonym stagospora) nodorum) on cereals (spot blight); grape hook silk shell (Uncinula (synonym Erysiphe) necator) on grape vine (powdery mildew, asexual: oidium tuckeri); corn (e.g., alternaria corn (s. Turcicum), synonymous with alternaria alternata (Helminthosporium turcicum)) and alternaria species (Setospaeria) on turf (leaf blight); Maize (e.g., head smut), millet and cane of the genus nigella (Sphacelotheca) (smut); powdery mildew (Sphaerotheca fuliginea) of the species Sphaerotheca fuliginea (powdery mildew) on cucurbitaceae; eschar (Spongosporasubterranea) on potatoes (eschar disease) and viral diseases transmitted thereby; the genus Phyllospora (Staganospora) on cereals, such as the species Phyllospora (S.nodorum) on wheat (Spot blight, sexual: leptosphaeria (synonym Phaeosphaeria) nodorum); Potato canceration germ (Synchytrium endobioticum) on potatoes (potato canceration disease); exocyst genus (Taphrina), such as exocyst malformation (t.de) on peach (mosaic disease) and exocyst prune (t.prune) of Li Shang; rhizopus (Thielaviopsis) on tobacco, pome fruits, vegetables, soybeans and cotton (black root rot), for example, black root rot fungus (t. Basicola) (synonym CHALARAELEGANS); tilletia (Tilletia) on cereals, such as T.tritici (synonyms T.caries, wheat stinking smut) and T.controller; The sarcoidosis (Typhula incarnata) on barley or wheat (gray snow rot); melanogaster (Urocystis), such as cryptomelane (U.oculta) on rye; monospora (Uromyces) on vegetables such as beans (e.g., alteromonas wart (u. Appendiculatus), synonyms u. Phaseoli) and sugar beets (e.g., betana (u. Betae)) (rust); cereal (e.g., wheat middlex (U.nuda) and U.avena enae), maize (e.g., maize smut) (U.maydis) and cane blackfungus genus (Ustilago) (smut); Apples (e.g. apple scab (v. Inaequallis)) and black fungus (venturi) on pears; and Verticillium (wilt) on various plants such as fruit trees and ornamental trees, vines, berries, vegetables and field crops, for example Verticillium (v.dahlia) on strawberries, oilseed rape, potatoes and tomatoes.
Advantageous effects
Due to the adoption of the technical scheme, the invention has the beneficial effects that:
The technical scheme of the invention has higher efficiency, better selectivity and safety for preventing and controlling plant diseases, can be used for agricultural or forestry sterilization, has excellent biological activity especially for common plant diseases generated by basidiomycota, ascomycota and fungi imperfecti pathogens, has excellent activity and selectivity especially for apple ring rot, peach brown rot, white powdery disease, wheat sheath blight, rice sheath blight, soybean rust, corn rust and the like, and has outstanding crop safety for crops.
Embodiments of the invention
The technical solutions in the embodiments of the present invention will be clearly and completely described below in connection with the embodiments of the present invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
By comprehensively considering the economy, diversity and bioactivity of the synthesized compounds, it is preferred that some of the compounds are listed in the following table. Specific compound structures are shown in table 1, and specific compound physical property data are shown in table 2. The compounds of tables 1-2 are only for better illustration of the present invention and are not meant to limit the present invention, and those skilled in the art should not understand that the scope of the above subject matter of the present invention is limited to the following compounds.
TABLE 1 Structure of Compounds of formula I
Sequence number R1 Sequence number R1
1 CN 16 CCl3
2 F 17 CHCl2
3 Cl 18 CHF2
4 Br 19 CH2CCl3
5 I 20 CH2CHF2
6 Me 21 Methoxy group
7 Et 22 Ethoxy group
8 n-Pr 23 Propoxy group
9 i-Pr 24 Isopropoxy group
10 n-Bu 25 N-butoxy
11 i-Bu 26 Sec-butoxy radical
12 s-Bu 27 Isobutoxy groups
13 t-Bu 28 Tert-butoxy radical
14 CF3 29 Cyclopropane base
15 CBr3 30 Cyclohexane radical
TABLE 2 1 H NMR data
The process for preparing the compounds of the present invention is illustrated in the following schemes and examples. The starting materials are commercially available or can be prepared by methods known in the literature or as shown in detail. Those skilled in the art will appreciate that other synthetic routes may also be used to synthesize the compounds of the present invention. Although specific starting materials and conditions in the synthetic routes have been described below, they may be readily replaced with other similar starting materials and conditions, and variations or modifications to the preparation methods of the present invention, such as various isomers of the compounds, are included within the scope of the present invention. In addition, the preparation methods described below may be further modified in accordance with the present disclosure using conventional chemical methods well known to those skilled in the art. For example, protection of the appropriate groups during the reaction, and the like.
Example 1
The preparation method of the compound I-1 comprises the following steps:
(1) Preparation of 2-cyano-4- (4-chlorophenoxy) acetophenone:
in a dry 500mL single-neck flask, parachlorophenol (12.86 g,0.1 mol) was dissolved in 200mL DMF, 2-cyano-4-fluoroacetophenone (16.30 g,0.1 mol) was added with stirring at room temperature, potassium carbonate (27.64 g,0.2 mol), and the reaction mixture was heated to 90℃for 2h. The LC-MS monitors the reaction, and after the reaction is finished, the solution is filtered while the solution is hot, and the solution is left to cool to room temperature. 400mL of ice water is prepared, the liquid phase is slowly dripped into the ice water which is continuously stirred, the stirring is carried out for 10 to 20 minutes, the separated product is filtered, and the target product (22.66 g, the yield is 83.6%) is obtained by drying.
(2) Preparation of 2- (2-bromoacetyl) -5- (4-chlorophenoxy) benzonitrile:
The product of the first step was placed in a dry 500mL single-neck flask, dissolved in 200mL of HF and a catalytic amount of aluminum trichloride (0.13 g,0.001 mol) was added. Bromine (13.36 g,0.084 mol) is weighed by a differential method, 2 drops of bromine are slowly added dropwise into the reaction system to initiate reaction under stirring at room temperature, the reaction system is transferred into an ice water bath after initiation, and the rest bromine is slowly added dropwise. The reaction was monitored by LC-MS and after completion of the reaction, the desired product (25.44 g, 87.2% yield) was obtained by concentration under reduced pressure.
(3) Preparation of Compound I-1:
The product of the previous step was dissolved in dry tetrahydrofuran for use, 200mL of dry THF was added to a dry 500mL single-neck flask, triazole (6.56 g,0.095 mol) was added under stirring at room temperature, sodium hydride (content 60%,3.80g,0.095 mol) was added in portions, and after stirring at room temperature for 20min, the tetrahydrofuran solution of the product of the previous step was added dropwise to the reaction system, and the mixture was transferred into an oil bath at 50℃for 2 hours of reaction. LC-MS monitors the reaction, after the reaction is finished, the reaction mixture is concentrated under reduced pressure, and the product is separated by column chromatography (eluent is petroleum ether: ethyl acetate=4:1) to obtain a target product I-1 (21.12 g, 85.7%).
Example 2
The preparation method of the compound I-3 comprises the following steps:
(1) Preparation of 2-chloro-4- (4-chlorophenoxy) acetophenone:
In a dry 500mL single-neck flask, parachlorophenol (12.86 g,0.1 mol) was dissolved in 200mL DMF, 2-chloro-4-fluoroacetophenone (17.20 g,0.1 mol) was added with stirring at room temperature, potassium carbonate (27.64 g,0.2 mol), and the reaction mixture was heated to 90℃for 2h. The LC-MS monitors the reaction, and after the reaction is finished, the solution is filtered while the solution is hot, and the solution is left to cool to room temperature. 400mL of ice water is prepared, the liquid phase is slowly dripped into the ice water which is continuously stirred, the stirring is carried out for 10 to 20 minutes, the separated product is filtered, and the target product (24.61 g, yield is 87.9%) is obtained by drying.
(2) Preparation of 2-bromo-1- (2-chloro-4- (4-chlorophenoxy) phenyl) ethan-1-one:
The product of the first step was placed in a dry 500mL single-neck flask, dissolved in 200mL of HF and a catalytic amount of aluminum trichloride (0.13 g,0.001 mol) was added. Bromine (14.06 g,0.088 mol) is weighed by a differential method, 2 drops of bromine are slowly added dropwise into the reaction system to initiate reaction under stirring at room temperature, the reaction system is shifted into an ice water bath after initiation of the reaction, and the residual bromine is slowly added dropwise. The reaction was monitored by LC-MS, and after the reaction was completed, the reaction was concentrated under reduced pressure to give the desired product (25.58 g, yield 81.3%).
(3) Preparation of Compound I-3:
The product of the previous step was dissolved in dry tetrahydrofuran for use, 200mL of dry THF was added to a dry 500mL single-neck flask, triazole (6.42 g,0.093 mol) was added under stirring at room temperature, sodium hydride (content 60%,3.72g,0.093 mol) was added in portions, and after stirring at room temperature for 20 minutes, the tetrahydrofuran solution of the product of the previous step was added dropwise to the reaction system, and the mixture was transferred into an oil bath at 50℃for 2 hours of reaction. LC-MS monitors the reaction, after the reaction is finished, the reaction mixture is concentrated under reduced pressure, and the product is separated by column chromatography (eluent is petroleum ether: ethyl acetate=4:1) to obtain a target product I-3 (21.60 g, 87.1%).
Example 3
The preparation method of the compound I-13 comprises the following steps:
(1) Preparation of 2-tert-butyl-4- (4-chlorophenoxy) acetophenone:
In a dry 500mL single-neck flask, parachlorophenol (12.86 g,0.1 mol) was dissolved in 200mL DMF, 4-fluoro-2-tert-butylacetophenone (19.41 g,0.1 mol) was added with stirring at room temperature, potassium carbonate (27.64 g,0.2 mol), and the reaction mixture was heated to 90℃for 2h. The LC-MS monitors the reaction, and after the reaction is finished, the solution is filtered while the solution is hot, and the solution is left to cool to room temperature. 400mL of ice water is prepared, the liquid phase is slowly dripped into the ice water which is continuously stirred, the stirring is carried out for 10 to 20 minutes, the separated product is filtered, and the target product (26.04 g, the yield is 86.2%) is obtained by drying.
(2) Preparation of 2-bromo-1- (2- (tert-butyl) -4- (4-chlorophenoxy) phenyl) ethan-1-one:
The product of the first step was placed in a dry 500mL single-neck flask, dissolved in 200mL of HF and a catalytic amount of aluminum trichloride (0.13 g,0.001 mol) was added. Bromine (13.77 g,0.0862 mol) is weighed by a differential method, 2 drops of bromine are slowly added dropwise into the reaction system to initiate reaction under stirring at room temperature, the reaction system is transferred into an ice water bath after initiation of the reaction, and the residual bromine is slowly added dropwise. The reaction was monitored by LC-MS, and after the reaction was completed, the reaction was concentrated under reduced pressure to give the desired product (26.80 g, yield 81.8%).
(3) Preparation of Compound I-13:
The product of the previous step was dissolved in dry tetrahydrofuran for use, 200mL of dry THF was added to a dry 500mL single-neck flask, triazole (6.35 g,0.092 mol) was added under stirring at room temperature, sodium hydride (content 60%,3.68g,0.092 mol) was added in portions, and after stirring at room temperature for 20min, the tetrahydrofuran solution of the product of the previous step was added dropwise to the reaction system, and the mixture was transferred into an oil bath at 50℃for 2 hours of reaction. LC-MS monitors the reaction, after the reaction is finished, the reaction mixture is concentrated under reduced pressure, and the product is separated by column chromatography (eluent is petroleum ether: ethyl acetate=4:1) to obtain a target product I-13 (22.28 g, 89.3%).
Example 4
The preparation method of the compound I-14 comprises the following steps:
(1) Preparation of 2-trifluoromethyl-4- (4-chlorophenoxy) acetophenone:
In a dry 500mL single-neck flask, parachlorophenol (12.86 g,0.1 mol) was dissolved in 200mL DMF, and 4-fluoro-2-trifluoromethyl acetophenone (20.60 g,0.1 mol), potassium carbonate (27.64 g,0.2 mol) was added with stirring at room temperature, and the reaction mixture was heated to 90℃for 2h. The LC-MS monitors the reaction, and after the reaction is finished, the solution is filtered while the solution is hot, and the solution is left to cool to room temperature. 400mL of ice water is prepared, the liquid phase is slowly dripped into the ice water which is continuously stirred, the stirring is carried out for 10 to 20 minutes, the separated product is filtered, and the target product (26.44 g, the yield is 84.2%) is obtained by drying.
(2) Preparation of 2-bromo-1- (4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl) ethan-1-one:
The product of the first step was placed in a dry 500mL single-neck flask, dissolved in 200mL of HF and a catalytic amount of aluminum trichloride (0.13 g,0.001 mol) was added. Bromine (13.46 g,0.084 mol) is weighed by a differential method, 2 drops of bromine are slowly added dropwise into the reaction system to initiate reaction under stirring at room temperature, the reaction system is transferred into an ice water bath after initiation of the reaction, and the residual bromine is slowly added dropwise. The reaction was monitored by LC-MS, and after the reaction was completed, the desired product (28.41 g, 86.1% yield) was obtained by concentration under reduced pressure.
(3) Preparation of Compound I-14:
The product of the previous step is dissolved in dry tetrahydrofuran for standby, 200mL of dry THF is added into a dry 500mL single-neck flask, triazole (6.49 g,0.094 mol) is added under stirring at room temperature, sodium hydride (content 60%,3.76g,0.094 mol) is added in batches, after stirring at room temperature for 20min, the tetrahydrofuran solution of the product of the previous step is added into the reaction system dropwise, and the reaction system is shifted into an oil bath at 50 ℃ for 2h. LC-MS monitors the reaction, after the reaction is finished, the reaction mixture is concentrated under reduced pressure, and the product is separated by column chromatography (eluent is petroleum ether: ethyl acetate=4:1) to obtain a target product I-14 (24.42 g, 88.4%).
Example 5
The preparation method of the compound I-21 comprises the following steps:
(1) Preparation of 2-methoxy-4- (4-chlorophenoxy) acetophenone:
In a dry 500mL single-neck flask, parachlorophenol (12.86 g,0.1 mol) was dissolved in 200mL DMF, 2-methoxy-4-fluoroacetophenone (16.81 g,0.1 mol) was added with stirring at room temperature, potassium carbonate (27.64 g,0.2 mol), and the reaction mixture was heated to 90℃for 2h. The LC-MS monitors the reaction, and after the reaction is finished, the solution is filtered while the solution is hot, and the solution is left to cool to room temperature. 400mL of ice water is prepared, the liquid phase is slowly dripped into the ice water which is continuously stirred, the stirring is carried out for 10 to 20 minutes, the separated product is filtered, and the target product (23.82 g, the yield is 86.3%) is obtained by drying.
(2) Preparation of 2-bromo-1- (4- (4-chlorophenoxy) -2-methoxyphenyl) ethan-1-one:
The product of the first step was placed in a dry 500mL single-neck flask, dissolved in 200mL of HF and a catalytic amount of aluminum trichloride (0.13 g,0.001 mol) was added. Bromine (13.79 g,0.086 mol) is weighed by a differential method, 2 drops of bromine are slowly added dropwise into the reaction system to initiate reaction under stirring at room temperature, the reaction system is shifted into an ice water bath after initiation of the reaction, and the residual bromine is slowly added dropwise. LC-MS monitoring reaction, after the reaction, concentrating under reduced pressure to obtain the target product (25.81 g, yield 84.5%).
(3) Preparation of Compound I-21:
The product of the previous step was dissolved in dry tetrahydrofuran for use, 200mL of dry THF was added to a dry 500mL single-neck flask, triazole (6.56 g,0.095 mol) was added under stirring at room temperature, sodium hydride (content 60%,3.80g,0.095 mol) was added in portions, and after stirring at room temperature for 20min, the tetrahydrofuran solution of the product of the previous step was added dropwise to the reaction system, and the mixture was transferred into an oil bath at 50℃for 2 hours of reaction. LC-MS monitors the reaction, after the reaction is finished, the reaction mixture is concentrated under reduced pressure, and the product is separated by column chromatography (eluent is petroleum ether: ethyl acetate=4:1) to obtain a target product I-21 (20.21 g, 80.8%).
Example 6
Preparation of the preparation:
1. Soluble liquid: 10-50% of the compound of formula (I) and 5-20% of a wetting agent are dissolved in water and/or a water-soluble solvent added to 100% to give the product.
2. Dispersible agent: 5-30% of the compound of formula (I) and 1-10% of a dispersant are dissolved in an organic solvent added to 100% to give the product.
3. Emulsifiable concentrate: 15-70% of the compound of formula (I) and 5-10% of an emulsifier are dissolved in a water-insoluble organic solvent added to 100% to give the product.
4. Aqueous emulsion: 5-40% of a compound of formula (I) and 1-10% of an emulsifier are dissolved in 20-40% of a water-insoluble organic solvent. The mixture was introduced into 100% water by means of an emulsifying machine and made into a homogeneous emulsion to obtain the product.
5. Suspending agent: crushing 20-60% of the compound of formula (I) in a stirred ball mill under water with the addition of 2-10% of dispersant and wetting agent, 0.1-2% of thickener and 100% of water to give a finely divided active substance suspension.
6. Water dispersible granule: grinding 50-80% of the compound of formula (I) with the addition of dispersant and wetting agent to 100% and preparing it into water dispersible granule by means of industrial production equipment.
All the above are weight percentages.
Example 7
Biological Activity evaluation (maize rust Puccinia sorghi):
Weighing a compound sample with a certain mass and a control compound, dissolving the compound sample and the control compound in acetone, and preparing a mother solution for standby. In the test, compound samples and control compounds were formulated into serial concentration gradient solutions with 0.05% tween 80 in water.
And when the second true leaves of the corn are fully unfolded, selecting corn seedlings with consistent growth vigor as test host plants.
The sprayer is a spray tower for measuring, spraying 30ml of liquid medicine every 2 basins, and naturally airing. After 24h, the pathogenic bacteria were inoculated and a blank control was set.
Preparing 0.05% Tween-80 water, placing the disease leaves with more spores into a wide-mouth bottle, adding a proper amount of warm water, shaking the wide-mouth bottle to shake the spores into Tween water, filtering the spores into a conical flask by using gauze to obtain spore suspension (200 spores can be observed under a microscope with a 10-time mirror), uniformly spraying the spore suspension onto corn seedling leaves by using a spray gun, placing the inoculated corn seedlings into an artificial climate chamber for 12 hours, transferring the corn seedlings into a greenhouse for culture, and investigating the disease condition according to a blank control after 7-10 days.
The results survey was made with reference to "A Manual of ASSESSMENT KEYS for PLANT DISEASES", written by the American society of plant diseases, and was expressed as 100 to 0, with a "100" scale representing no disease and a "0" scale representing the most severe degree of disease.
A portion of the compounds of the present invention were selected for biological activity testing with control compounds CK1-16, and control compounds CK1-14 had the following structure:
The test results were as follows:
when the concentration of the liquid medicine is 0.78ppm,
The compounds with the control effect above 90 levels are as follows: CK13 and CK14 in compounds 1-13, 15-22, 31-32, 39-40 and control compounds.
According to the method, partial compounds and control compounds CK13 and CK14 are selected for carrying out parallel measurement on the activity of preventing and treating corn rust, and experimental results are shown in the following table:
Control test for corn rust control:
Example 8
Biological Activity evaluation (wheat powdery mildew ERYSIPHE GRAMINIS):
weighing a compound sample with a certain mass and a control compound, dissolving the compound sample and the control compound in acetone, and preparing a mother solution for standby. In the test, compound samples and control compounds were formulated into serial concentration gradient solutions with 0.1% tween 80 in water for in vivo screening.
When the first leaf of wheat is fully unfolded, wheat seedlings with consistent growth vigor are selected as test host plants of wheat powdery mildew.
The sprayer is a spray tower for testing, spraying 30ml of liquid medicine for each treatment, and naturally airing. After 24h, the pathogenic bacteria were inoculated and a blank control was set.
The mature wheat powdery mildew spores are gently shaken off, evenly inoculated on wheat seedlings, cultivated in a greenhouse, and investigated according to the disease condition of a blank control after 7-10 d.
The results survey was made with reference to "A Manual of ASSESSMENT KEYS for PLANT DISEASES", written by the American society of plant diseases, and was expressed as 100 to 0, with a "100" scale representing no disease and a "0" scale representing the most severe degree of disease.
Part of the control test for wheat powdery mildew control activity of the compound of the invention and the control compound:
Example 9
Biological Activity evaluation (apple ring rot Botryosphaeria berengeriana f.sp.piricola):
Weighing a compound sample with a certain mass and a control compound, dissolving the compound sample and the control compound in acetone, and preparing a mother solution for standby. In the test, compound samples and control compounds were formulated into a series of concentration gradient solutions with 0.1% tween 80 in water for use in growth rate assay to determine apple ring rot activity.
Adding the diluted liquid medicine into a quantitative culture medium to prepare a PDA culture medium with medicine, inoculating a bacterial cake with apple ring rot germ with the diameter of 0.7cm, taking the culture medium with sterilized water as a blank control, repeating for 3 times for each treatment, and placing the culture medium into a constant temperature incubator at 25 ℃ for culturing. When the control colony grows up to the plane, the diameter of each treated colony is measured by a crisscross method, and the data are recorded and calculated to obtain the bacteriostasis rate.
Part of the control test for apple ring rot control activity of the compounds according to the invention and control compounds:
Numbering of compounds Concentration (ppm) Antibacterial rate
1 6.25 100
2 6.25 95
3 6.25 100
5 6.25 90
7 6.25 70
11 6.25 80
12 6.25 90
13 6.25 100
16 6.25 95
17 6.25 90
19 6.25 95
20 6.25 90
22 6.25 100
25 6.25 85
CK13 6.25 45
CK14 6.25 75
Example 10
Biological Activity evaluation (Monilia cinerea):
weighing a compound sample with a certain mass and a control compound, dissolving the compound sample and the control compound in acetone, and preparing a mother solution for standby. In the test, compound samples and control compounds are prepared into a series of concentration gradient liquid medicines by using water with 0.1% of Tween 80, and the liquid medicines are used for measuring the activity on brown rot of peach by a growth rate method.
Adding the diluted medicinal liquid into quantitative culture medium to obtain PDA culture medium with medicine, inoculating bacterial cake of brown rot of peach with diameter of 0.5cm, taking culture medium with sterilized water as blank control, repeating for 3 times, and culturing in constant temperature incubator at 25deg.C. When the control colony grows up to the plane, the diameter of each treated colony is measured by a crisscross method, and the data are recorded and calculated to obtain the bacteriostasis rate.
Partial compounds of the invention and control compounds control activity control tests for preventing and treating brown rot of peach:
Numbering of compounds Concentration (ppm) Antibacterial rate
1 6.25 95
2 6.25 90
3 6.25 100
5 6.25 95
7 6.25 90
11 6.25 85
12 6.25 90
13 6.25 100
16 6.25 95
17 6.25 95
19 6.25 90
20 6.25 90
22 6.25 100
25 6.25 90
CK13 6.25 90
CK14 6.25 90
The above embodiments are only for illustrating the technical concept and features of the present invention, and are intended to enable those skilled in the art to understand the content of the present invention and implement the same, and are not intended to limit the scope of the present invention. All equivalent changes or modifications made in accordance with the spirit of the present invention are intended to be included within the scope of the present invention.

Claims (3)

1. The application of the diphenyl ether compound containing the triazole structure in preventing and controlling plant diseases is characterized in that the plant diseases are plant diseases caused by pathogenic bacteria of ascomycota, basidiomycota or semi-known mycota, and the structural formula of the diphenyl ether compound is shown as the formula (I): in the formula (I), R 1 is Cl; the plant diseases caused by pathogenic bacteria of ascomycota, basidiomycota or Deuteromycota are corn rust, soybean rust, apple ring rot and peach brown rot.
2. A fungicidal composition for controlling or managing plant diseases, comprising a biologically effective amount of a compound of formula (I) as defined in claim 1 and a formulation carrier or formulation aid.
3. A method for controlling or controlling plant diseases, characterized in that a biologically effective amount of a compound of formula (I) according to claim 1 or a fungicidal composition according to claim 2 is applied to plants, plant propagation material or plant organs and cultivation media, cultivation material or cultivation spaces which grow subsequently; the plant diseases are corn rust, soybean rust, apple ring rot and peach brown rot.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0084597A1 (en) * 1981-10-10 1983-08-03 Bayer Ag Triazole and imidazole derivatives and pharmaceutical preparations containing them
CA1187084A (en) * 1981-10-10 1985-05-14 Hans-Ludwig Elbe Phenoxyphenyl azolylmethyl ketones and carbinols, processes for their preparation, and their use as fungicides and as intermediate products

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0084597A1 (en) * 1981-10-10 1983-08-03 Bayer Ag Triazole and imidazole derivatives and pharmaceutical preparations containing them
CA1187084A (en) * 1981-10-10 1985-05-14 Hans-Ludwig Elbe Phenoxyphenyl azolylmethyl ketones and carbinols, processes for their preparation, and their use as fungicides and as intermediate products

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