WO1999015491A1 - Composes ester et agents de lutte contre les parasites contenant lesdits composes comme principe actif - Google Patents

Composes ester et agents de lutte contre les parasites contenant lesdits composes comme principe actif Download PDF

Info

Publication number
WO1999015491A1
WO1999015491A1 PCT/JP1997/003400 JP9703400W WO9915491A1 WO 1999015491 A1 WO1999015491 A1 WO 1999015491A1 JP 9703400 W JP9703400 W JP 9703400W WO 9915491 A1 WO9915491 A1 WO 9915491A1
Authority
WO
WIPO (PCT)
Prior art keywords
parts
cis
compound
dimethyl
pest
Prior art date
Application number
PCT/JP1997/003400
Other languages
English (en)
Japanese (ja)
Inventor
Tomonori Iwasaki
Kazunori Tsushima
Mikako Nakamachi
Original Assignee
Sumitomo Chemical Company, Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to JP07371497A priority Critical patent/JP3826480B2/ja
Application filed by Sumitomo Chemical Company, Limited filed Critical Sumitomo Chemical Company, Limited
Priority to AU43203/97A priority patent/AU4320397A/en
Priority to PCT/JP1997/003400 priority patent/WO1999015491A1/fr
Priority to TW086114817A priority patent/TW340787B/zh
Priority to ZA979098A priority patent/ZA979098B/xx
Publication of WO1999015491A1 publication Critical patent/WO1999015491A1/fr

Links

Classifications

    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/743—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a three-membered ring and with unsaturation outside the ring

Definitions

  • the present invention relates to an ester compound and a pesticidal composition containing the same as an active ingredient.
  • Japanese Patent Publication No. 55-425-45 discloses that certain ester compounds are used as active ingredients such as insecticides. However, these compounds are not always always sufficient as active ingredients such as insecticides in terms of insecticidal efficacy.
  • the present inventors have conducted intensive studies to find a compound having an excellent pest control effect, and as a result, the ester compound represented by the following general formula 1 has an excellent pest control effect.
  • the present invention has been completed.
  • the present invention provides a compound represented by the following general formula 1:
  • R represents a C i Cs alkyl group (eg, a methyl group, an ethyl group, an isopropyl group, etc.), a C 2 -C 5 alkenyl group (eg, an aryl group, 3-butenyl) A C 2 -C 5 alkynyl group (eg, propargyl group, 3-butynyl group, etc.).
  • C i Cs alkyl group eg, a methyl group, an ethyl group, an isopropyl group, etc.
  • a C 2 -C 5 alkenyl group eg, an aryl group, 3-butenyl
  • a C 2 -C 5 alkynyl group eg, propargyl group, 3-butynyl group, etc.
  • a pesticidal composition comprising the same as an active ingredient.
  • the compounds of the present invention include stereoisomers (R / S) and geometric isomers (E / Z), but the present invention includes all stereoisomers having pest control activity, And mixtures thereof.
  • HC of the compound of the present invention represented by the general formula 1 a compound in which R is an ethyl group, an aryl group or a propyl group is particularly preferable.
  • Equation 2 The compound of the present invention can be produced, for example, by the following method. Equation 2:
  • Method c for reacting with an alcohol compound represented by Examples of the reactive derivative of the carboxylic acid compound of the formula 2 include an acid halide, and preferably an acid chloride.
  • the amount ratio of the raw materials used is usually 0.5 to 2 mol of the alcohol compound represented by the general formula 3 with respect to 1 mol of the sulfonic acid compound represented by the formula 2 or its reactive derivative.
  • the reaction is usually carried out by dicyclohexylcarbodiimide (DCC), 1-ethyl-3- (3-dimethyl).
  • a dehydrating agent such as (aminopropyl) carbodiimide hydrochloride (WSC)
  • the reaction is usually carried out in an organic solvent such as chloroform, dichloromethane, tetrahydrofuran (THF), benzene or toluene.
  • the amount of the dehydrating agent to be used is generally 1 to 5 mol per 1 mol of the carboxylic acid compound represented by the formula 2 or a reactive derivative thereof.
  • the reaction may be carried out in the presence of an organic base such as pyridine, triethylamine, 4-dimethylaminopyridine or diisopropylethylamine.
  • the reaction temperature is usually in the range of from 10 DC to + 100 ° C or the boiling point of the organic solvent used, preferably in the range of from 0 ° C to 30 ° C.
  • the reaction of the carboxylic acid compound represented by the formula 2 or its reactive derivative with the alcohol compound represented by the general formula 3 is usually carried out in an organic solvent such as dichloromethane, tetrahydrofuran (THF), benzene, and toluene.
  • the reaction is performed in the presence of a base such as gin, triethylamine and 4-dimethylaminopyridine.
  • the amount of the base to be used is generally 1 to 5 mol, per 1 mol of the carboxylic acid compound represented by the formula 2 or the reactive derivative thereof.
  • the reaction temperature is usually in the range of from 10 ° C to + 100 ° C or the boiling point of the organic solvent used, preferably from 0 ° C to + 30 ° C.
  • the reaction solution is subjected to ordinary post-treatments such as extraction with an organic solvent, washing, and concentration to isolate the target compound of the present invention. If necessary, it may be further purified by a usual operation such as chromatography.
  • the sulfonic acid compound represented by the formula 2 which is one of the intermediates for producing the compound of the present invention can be prepared, for example, according to the method described in Bull. Chem. Soc. Jpn, 4385-4394 (1987). Can be manufactured.
  • the alcohol compound represented by the general formula 3, which is another intermediate in producing the compound of the present invention can be produced, for example, according to the description in U.S. Pat.No. 4,263,463. .
  • Examples of pests against which the compound of the present invention exerts control effects include the following harmful insects and mites.
  • Black-billed beetle power brown beetle power
  • mosquitoes such as staghorn planthoppers, Tsumaguroyo-ki, Inazuma-kobayashi, Japanese white-headed tuna, etc., aphids, stink bugs, whiteflies, scale insects, hornworms, etc.
  • Ponds such as Nikameiga (Polygonidae), Kobunomeiga and Noshimekokuga, Spodoptera such as Spodoptera litura, Acapoto, Spodoptera, etc .; Agrotis spp., Heliothis spp., Konaga, Iga, Koiga etc.
  • House powers such as acaie power, kogatakae power, netaishima power, and hitos Butterflies such as Zishima, etc.
  • Anopheles such as Shinahamadara, Usurika, Houseflies such as house fly, oye fly, Himee fly, etc. Drosophila, tabby, bu, flies, etc.
  • Corn roots such as estancon worms, Southern corn worms, etc., Scarabaeidae such as Kunebuoyi, Himekogane etc. , Beetles such as leaf beetles, beetles, beetles, Epilachna spp, such as tentacled beetles, beetles beetles, beetles beetles, beetles beetles, beetles beetle, etc.
  • Hymenoptera pests are:
  • Harmful insects such as
  • Nisenamihadani Namihadani, Kanzahadani, Citrus spider mite, Apple Hadani etc.
  • the compound of the present invention When the compound of the present invention is used as an active ingredient of a pesticidal agent, it is usually necessary to mix it with a solid carrier, liquid carrier, gaseous carrier, or bait, or impregnate it into a base material such as mosquito coil or mat. If necessary, add surfactants and other pharmaceutical auxiliaries to add oils, emulsions, wettable powders, suspensions in water, emulsions in water, etc., granules, powders, aerosols, etc.
  • Mosquito coils electric mosquito coils, no mats (liquid electric mosquito coils: liquid-absorbent wicking device for insecticide), etc., self-burning type smokers, chemical reaction type smokers, porous ceramics It is formulated into non-heated fumigants, such as heated fumigation agents such as plate fumigation agents, resin evaporants and impregnated paper evaporants, fogging agents such as fogging, ULV agents, and poison baits.
  • heated fumigation agents such as plate fumigation agents, resin evaporants and impregnated paper evaporants
  • fogging agents such as fogging, ULV agents, and poison baits.
  • These preparations usually contain the compound of the present invention as an active ingredient in an amount of 0.001 to 95% by weight.
  • solid carriers used in the formulation include clays (kaolin clay, diatomaceous earth, synthetic hydrous silicon oxide, bentonite, fubasami clay, acid clay, etc.), talcs, ceramics, and other inorganic minerals (cericite).
  • the stone Fine powders or granular materials such as British, sulfur, activated carbon, calcium carbonate, hydrated silica, etc., and chemical fertilizers (ammonium sulfate, phosphorous ammonium, ammonium nitrate, urea, salt ammonium, etc.).
  • the liquid carrier include water, alcohols (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons
  • the gaseous carrier that is, propellant, include chlorofluorocarbon gas, butane gas, LPG (
  • surfactant examples include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and their polyoxyethylenates, polyethylene glycol ethers, and polyhydric alcohol esters. And sugar alcohol derivatives.
  • Examples of pharmaceutical adjuvants such as fixatives and dispersants include casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginate sugar), lignin derivatives, bentonite, sugars, and synthetic water-soluble polymers.
  • Examples of stabilizers include PAP (isopropyl acid phosphate) and BHT (2,6-di-tert-butyl-14-methylphenol). ), BHA (2-tert-butyl-4-methoxyphenol and 3-tert-butyl-14-methacrylate)
  • a mixture with xyphenol vegetable oils, mineral oils, surfactants, fatty acids or esters thereof, and the like.
  • the base material of the mosquito coil includes, for example, a mixture of a raw plant powder such as wood flour and cake flour with a binder such as tub flour, starch, glutin and the like.
  • Examples of the base material of the electric mosquito collection include a plate-like solidified fibril of a cotton linter or a mixture of a cotton linter and pulp.
  • the base components of the self-burning type smoke agent include, for example, combustion heating agents such as nitrates, nitrites, guanidine salts, potassium chlorate, nitrocellulose, ethylcellulose, and wood flour; alkali metal salts; alkaline earths Thermal decomposition stimulants such as metal salts, dichromates and chromates; oxygen supply agents such as potassium nitrate; flame retardants such as melamine and wheat starch; extenders such as diatomaceous earth; binders such as synthetic paste Are listed.
  • the base components of the chemical reaction type smoke agent include, for example, exothermic agents such as sulfides of alkali metals, polysulfides, hydrosulfides, hydrated salts, calcium oxide, carbonaceous materials, iron carbide, activated clay, etc.
  • exothermic agents such as sulfides of alkali metals, polysulfides, hydrosulfides, hydrated salts, calcium oxide, carbonaceous materials, iron carbide, activated clay, etc.
  • examples include catalyst agents, organic blowing agents such as azodicarbonamide, benzenesulfonylhydrazide, dinitrosopentamethylenetetramine, polystyrene, and polyurethane, and fillers such as natural fiber fragments and synthetic fiber fragments.
  • Examples of the base material of the non-heated evaporant include thermoplastic resin, filter paper, Japanese paper, and the like.
  • the base components of poison bait include, for example, bait components such as cereal flour, vegetable oil, sugar, and crystalline cellulose; antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid; preservatives such as dehydroacetic acid; and pepper. Powders, etc., and preventive agents such as cheese flavor, onion flavor, peanut oil, etc. Can be
  • Formulations of flowables generally contain 1 to 75% of the compound in 0.5 to 15% of a dispersant, 0.1 to 10% of a suspension aid (eg, protected colloids).
  • a suspension aid eg, protected colloids
  • suitable auxiliary agents for example, antifoaming agent, antibacterial agent, stabilizer, spreading agent, penetration aid, antifreezing agent, antibacterial agent, antibacterial agent
  • It can be obtained by finely dispersing in water containing a fungicide. Instead of water, it is also possible to use an oil in which the compound hardly dissolves as an oil suspension.
  • the protective colloid for example, gelatin, casein, gums, cellulose ester, polyvinyl alcohol and the like are used.
  • the compound imparting thixotropic properties include bentonite, aluminum magnesium silicate, xanthan gum, polyacrylic acid, and the like.
  • the preparation thus obtained is used as it is or diluted with water or the like. Also mixed with or without other pesticides, acaricides, nematicides, soil pesticides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners Can be used simultaneously.
  • insecticides and acaricides used include, for example, Huunitrothion
  • Ditromidazolidine such as imidacloprid [1- (6-chloro-3-pyridylmethyl) -N-nitroimidazolidin-1-2-iridenamine] Derivative, chlorfluazurone [1- (3,5-dichloro-1-4- (3-chloro-1-5-trifluoromethylpyridine-12-yloxy) phenyl) -13- (2,6-difluor Lobenzoyl) ⁇ rea], tefluvenzuron [1- (3,5-dichloro-1,2,4-difluorophenyl) 13- (2,6-difluorobenzoyl) ⁇ rea], flufenoxuron 1— (4— (2-chloro-1-4-trifluoromethylphenoxy) -1-fluorophenyl] —3 -— (2,6-difluorobenzoyl) ⁇ rea], difluvenzuron [1— ( Benzoyl pheny
  • the application concentration is 0.1 to 1 000 ppm, and the granules, dusts, etc. are applied as is, without any dilution.
  • Emulsions, wettable powders, flowables, etc. are diluted with water to 0.1-10000 ppm when used as an active ingredient for oils, aerosols, fumigants, smokers, transpirants, aerosols, ULV, etc. Etc. are applied as they are.
  • reaction solution was poured into ice-cooled 5% citric acid, extracted three times with ethyl ether, the ether layers were combined, washed successively with saturated saline, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. Distilled off.
  • reaction solution was poured into ice-cooled 5% aqueous citric acid, Extracted three times with ethyl ether. The ether layers were combined, washed sequentially with saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • reaction solution was poured into ice-cooled 5% aqueous solution of citric acid and extracted three times with getyl ether.
  • the ether layers were combined, washed sequentially with saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • Xanthan gum 0.2 part of Xanthan gum and 1.0 part of Vegum R (aluminum magnesium silicate manufactured by Sanyo Chemical) are dispersed in 58.8 parts of ion-exchanged water to obtain a thickener solution.
  • Vegum R aluminum magnesium silicate manufactured by Sanyo Chemical
  • each of the compounds (1) to (14) is dissolved in 5 parts of dichloromethane, and this is mixed with 94.9 parts of deodorized kerosene to obtain each 0.1% oil solution.
  • each of the compounds (1) to (14) was dissolved in 20 ml of acetone, and a carrier for mosquito coils (tab powder: kashiwa powder: wood powder mixed in a ratio of 4: 3: 3) was mixed with 99.7 g. After uniformly stirring and mixing, 12 Om 1 of water is added, and the well-kneaded one is molded and dried to obtain each mosquito coil.
  • Formulation example 11 Electric mosquito collection mat
  • Acetone is added to 0.8 g of each of compounds (1) to (14) and 0.4 g of piperonyl butoxide, and dissolved to make a total of 1 Om1.
  • 0.5 ml of this solution was uniformly impregnated into a 2.5 cm x 1.5 cm, 0.3 cm thick electric mat substrate (solidified fibril of a mixture of cotton linter and pulp in a plate shape), and each electric Obtain mosquito repellent.
  • each of compounds (1) to (14) 3 parts are dissolved in 97 parts of deodorized kerosene, put in a vinyl chloride container, and the upper part is made of a liquid-absorbing wick that can be heated with a heater. Sinter) to obtain each liquid electric mosquito.
  • Test Examples show that the compound of the present invention is useful as an active ingredient of a pesticidal agent.
  • the compounds of the present invention have the above compound numbers, and the compounds used as comparative controls are shown by the compound symbols in Table 1.
  • Test Example 1 Insecticidal test of house flies by volatilization at room temperature

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des composés ester de la formule générale (I), qui présentent une excellente activité antiparasitaire et s'utilisent de ce fait comme principe actif dans des agents de lutte contre les parasites. Dans cette formule, R désigne alkyle C1-C5, alkényle C2-C5 ou alkinyle C2-C5.
PCT/JP1997/003400 1996-03-28 1997-09-25 Composes ester et agents de lutte contre les parasites contenant lesdits composes comme principe actif WO1999015491A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP07371497A JP3826480B2 (ja) 1996-03-28 1997-03-26 エステル化合物およびそれを有効成分とする有害生物防除剤
AU43203/97A AU4320397A (en) 1997-09-25 1997-09-25 Ester compounds and pest-controlling agents containing the same as the active ingredient
PCT/JP1997/003400 WO1999015491A1 (fr) 1996-03-28 1997-09-25 Composes ester et agents de lutte contre les parasites contenant lesdits composes comme principe actif
TW086114817A TW340787B (en) 1996-03-28 1997-10-09 Ester compounds and harmful organism-controlling agents containing them as active ingredients
ZA979098A ZA979098B (en) 1996-03-28 1997-10-10 Ester compounds and harmful organism-controlling agents containing them as active ingredients

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP7447396 1996-03-28
JP07371497A JP3826480B2 (ja) 1996-03-28 1997-03-26 エステル化合物およびそれを有効成分とする有害生物防除剤
PCT/JP1997/003400 WO1999015491A1 (fr) 1996-03-28 1997-09-25 Composes ester et agents de lutte contre les parasites contenant lesdits composes comme principe actif
ZA979098A ZA979098B (en) 1996-03-28 1997-10-10 Ester compounds and harmful organism-controlling agents containing them as active ingredients

Publications (1)

Publication Number Publication Date
WO1999015491A1 true WO1999015491A1 (fr) 1999-04-01

Family

ID=27465613

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1997/003400 WO1999015491A1 (fr) 1996-03-28 1997-09-25 Composes ester et agents de lutte contre les parasites contenant lesdits composes comme principe actif

Country Status (3)

Country Link
JP (1) JP3826480B2 (fr)
WO (1) WO1999015491A1 (fr)
ZA (1) ZA979098B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101575291B (zh) * 2009-06-25 2012-10-03 江苏扬农化工股份有限公司 一种拟除虫菊酯化合物及其制备方法和应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63280044A (ja) * 1987-05-12 1988-11-17 Sumitomo Chem Co Ltd エステル化合物およびそれを有効成分とする殺虫剤
JPH0222248A (ja) * 1988-06-03 1990-01-25 Sumitomo Chem Co Ltd エステル化合物およびその殺虫、殺ダニ剤としての用途
JPH02282309A (ja) * 1988-11-22 1990-11-19 Sumitomo Chem Co Ltd 殺虫、殺ダニ方法
JPH05163205A (ja) * 1991-12-13 1993-06-29 Dainippon Jochugiku Co Ltd 新規シクロプロパンカルボン酸エステル誘導体、及び これを含有する殺虫、殺ダニ剤ならびに忌避剤

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63280044A (ja) * 1987-05-12 1988-11-17 Sumitomo Chem Co Ltd エステル化合物およびそれを有効成分とする殺虫剤
JPH0222248A (ja) * 1988-06-03 1990-01-25 Sumitomo Chem Co Ltd エステル化合物およびその殺虫、殺ダニ剤としての用途
JPH02282309A (ja) * 1988-11-22 1990-11-19 Sumitomo Chem Co Ltd 殺虫、殺ダニ方法
JPH05163205A (ja) * 1991-12-13 1993-06-29 Dainippon Jochugiku Co Ltd 新規シクロプロパンカルボン酸エステル誘導体、及び これを含有する殺虫、殺ダニ剤ならびに忌避剤

Also Published As

Publication number Publication date
JP3826480B2 (ja) 2006-09-27
ZA979098B (en) 1998-10-28
JPH09316035A (ja) 1997-12-09

Similar Documents

Publication Publication Date Title
JP4285045B2 (ja) エステル化合物およびその用途
JP3991812B2 (ja) エステル化合物およびその用途
JP3690215B2 (ja) ピレスロイド化合物およびそれを有効成分として含有する有害生物防除剤
JP5526472B2 (ja) エステル化合物及びその用途
JP2008201731A (ja) 有害生物防除剤組成物及び有害生物の防除方法
JP5012095B2 (ja) エステル化合物およびその用途
JP4552456B2 (ja) エステル化合物およびその用途
JP2010173951A (ja) シクロプロパンカルボン酸エステル及びその用途
JPH11335331A (ja) ピレスロイド化合物および該化合物を含有する害虫防除剤
JP2010047561A (ja) エステル化合物及びその用途
JP2018048095A (ja) エステル化合物及びその用途
JP5066843B2 (ja) エステル化合物及びその有害生物防除用途
JP4029486B2 (ja) エステル化合物
WO1999015491A1 (fr) Composes ester et agents de lutte contre les parasites contenant lesdits composes comme principe actif
JP3882209B2 (ja) エステル化合物およびそれを有効成分とする有害生物防除剤
JP5076623B2 (ja) エステル化合物及びその有害生物防除用途
JP5070843B2 (ja) エステル化合物及びその用途
JP3694915B2 (ja) エステル化合物およびそれを有効成分とする有害生物防除剤
JP5141148B2 (ja) エステル化合物及びその用途
JP2009149570A (ja) シクロプロパンカルボン酸エステル及びその用途
JP4003336B2 (ja) エステル化合物
JP2002249464A (ja) エステル化合物およびそれを有効成分として含有する有害生物防除剤
JP2008208105A (ja) エステル化合物及びその用途
JP2000026210A (ja) スパチュレノールを有効成分とする殺虫剤
JP4269410B2 (ja) ピレスロイド化合物及びそれを有効成分とする害虫防除剤

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU BR CN HU ID KR MX RU TR UA US VN

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE

121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase