RU2017104513A - Производные бис(арил)катехина в качестве гербицидов - Google Patents

Производные бис(арил)катехина в качестве гербицидов Download PDF

Info

Publication number
RU2017104513A
RU2017104513A RU2017104513A RU2017104513A RU2017104513A RU 2017104513 A RU2017104513 A RU 2017104513A RU 2017104513 A RU2017104513 A RU 2017104513A RU 2017104513 A RU2017104513 A RU 2017104513A RU 2017104513 A RU2017104513 A RU 2017104513A
Authority
RU
Russia
Prior art keywords
compound according
methyl
represents halogen
chloropyridin
yloxy
Prior art date
Application number
RU2017104513A
Other languages
English (en)
Russian (ru)
Other versions
RU2017104513A3 (enExample
Inventor
Рависекхара Почимиредди РЕДДИ
Лакшми БАЛАГОПАЛ
Паула Луиз Шарп
Original Assignee
Е.И.Дюпон Де Немур Энд Компани
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
Application filed by Е.И.Дюпон Де Немур Энд Компани filed Critical Е.И.Дюпон Де Немур Энд Компани
Publication of RU2017104513A publication Critical patent/RU2017104513A/ru
Publication of RU2017104513A3 publication Critical patent/RU2017104513A3/ru

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32One oxygen, sulfur or nitrogen atom
    • C07D239/34One oxygen atom
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/541,3-Diazines; Hydrogenated 1,3-diazines
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/581,2-Diazines; Hydrogenated 1,2-diazines
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/7071,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/761,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/781,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fertilizers (AREA)
RU2017104513A 2014-07-14 2015-07-01 Производные бис(арил)катехина в качестве гербицидов RU2017104513A (ru)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201462024414P 2014-07-14 2014-07-14
US62/024,414 2014-07-14
US201562166759P 2015-05-27 2015-05-27
US62/166,759 2015-05-27
PCT/US2015/038778 WO2016010731A1 (en) 2014-07-14 2015-07-01 Bis(aryl)catechol derivatives as herbicides

Publications (2)

Publication Number Publication Date
RU2017104513A true RU2017104513A (ru) 2018-08-15
RU2017104513A3 RU2017104513A3 (enExample) 2019-01-29

Family

ID=53682826

Family Applications (1)

Application Number Title Priority Date Filing Date
RU2017104513A RU2017104513A (ru) 2014-07-14 2015-07-01 Производные бис(арил)катехина в качестве гербицидов

Country Status (19)

Country Link
US (1) US20170190671A1 (enExample)
EP (1) EP3169676A1 (enExample)
JP (1) JP2017522317A (enExample)
KR (1) KR20170032355A (enExample)
CN (1) CN106488913A (enExample)
AU (1) AU2015290153A1 (enExample)
BR (1) BR112017000745A2 (enExample)
CA (1) CA2954627A1 (enExample)
CL (1) CL2017000103A1 (enExample)
CO (1) CO2017000337A2 (enExample)
IL (1) IL249841A0 (enExample)
MX (1) MX2017000594A (enExample)
PE (1) PE20170439A1 (enExample)
RU (1) RU2017104513A (enExample)
SG (1) SG11201700033YA (enExample)
TW (1) TW201625554A (enExample)
UY (1) UY36210A (enExample)
WO (1) WO2016010731A1 (enExample)
ZA (1) ZA201700119B (enExample)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PE20161143A1 (es) 2014-01-16 2016-11-18 Du Pont Derivados de pirimidiniloxi benceno como herbicidas
RU2735278C2 (ru) 2015-03-18 2020-10-29 ЭфЭмСи Корпорейшн Замещенные производные пиримидинилокси-пиридина в качестве гербицидов
TWI713530B (zh) 2015-06-05 2020-12-21 美商艾佛艾姆希公司 作為除草劑之嘧啶氧基苯衍生物
BR112018000687B1 (pt) 2015-07-13 2021-05-04 Fmc Corporation composto, composições herbicidas, misturas herbicidas e métodos para o controle do crescimento de vegetação indesejada
TW201904947A (zh) 2017-05-02 2019-02-01 美商富曼西公司 作為除草劑的嘧啶氧基苯稠合化合物
WO2020002089A1 (de) 2018-06-25 2020-01-02 Bayer Aktiengesellschaft Substituierte 2-heteroaryloxypyridine sowie deren salze und ihre verwendung als herbizide wirkstoffe
UA129288C2 (uk) * 2018-09-27 2025-03-12 ЕфЕмСі КОРПОРЕЙШН Піридазинонові гербіциди і піридазинонові проміжні продукти, які використовуються для отримання гербіциду
EP3670505A1 (de) 2018-12-18 2020-06-24 Bayer AG Substituierte pyridinyloxybenzole sowie deren salze und ihre verwendung als herbizide wirkstoffe
EP3947350A1 (de) * 2019-03-27 2022-02-09 Bayer Aktiengesellschaft Substituierte 2-heteroarylaminobenzole sowie deren salze und ihre verwendung als herbizide wirkstoffe
GB202005175D0 (en) * 2020-04-08 2020-05-20 Syngenta Crop Protection Ag Improvements in or relating to organic compounds
US20240174618A1 (en) 2021-02-04 2024-05-30 Bayer Aktiengesellschaft Substituted (2-heteroaryloxyphenyl)sulfonates, salts thereof and their use as herbicidal agents
JP2025512828A (ja) * 2022-03-28 2025-04-22 バイエル・アクチエンゲゼルシヤフト 置換2-アミノアジンおよびその塩、ならびにその除草性活性物質としての使用
CN118974024A (zh) 2022-03-28 2024-11-15 拜耳公司 取代的2-c-吖嗪及其盐以及作为除草活性物质的用途

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2891855A (en) 1954-08-16 1959-06-23 Geigy Ag J R Compositions and methods for influencing the growth of plants
US3235361A (en) 1962-10-29 1966-02-15 Du Pont Method for the control of undesirable vegetation
US3060084A (en) 1961-06-09 1962-10-23 Du Pont Improved homogeneous, readily dispersed, pesticidal concentrate
US3299566A (en) 1964-06-01 1967-01-24 Olin Mathieson Water soluble film containing agricultural chemicals
US3309192A (en) 1964-12-02 1967-03-14 Du Pont Method of controlling seedling weed grasses
US4144050A (en) 1969-02-05 1979-03-13 Hoechst Aktiengesellschaft Micro granules for pesticides and process for their manufacture
US3920442A (en) 1972-09-18 1975-11-18 Du Pont Water-dispersible pesticide aggregates
US4172714A (en) 1976-12-20 1979-10-30 E. I. Du Pont De Nemours And Company Dry compactible, swellable herbicidal compositions and pellets produced therefrom
NZ188244A (en) * 1977-09-13 1981-04-24 Ici Australia Ltd 2-substituted pyrimidines compositions growth regulating processes
DE2847662A1 (de) * 1977-11-04 1979-05-10 Ciba Geigy Ag Verfahren zur herstellung von hydroxydiarylaethern
JPS5524195A (en) * 1978-08-08 1980-02-21 Ici Australia Ltd Herbicide compound and composition*their manufacture and their use
NZ191078A (en) * 1978-08-08 1982-05-31 Ici Australia Ltd Bis(pyrimidyloxy) benzenes bis(pyrimidylthio)benzenes and prymidyloxy-pyrimidyl thiobenzens and herbicidal compositions
US4371736A (en) * 1981-03-27 1983-02-01 E. I. Du Pont De Nemours And Company Herbicidal pyridinyloxy(pyrimidinyloxy)benzenes
GB2095558B (en) 1981-03-30 1984-10-24 Avon Packers Ltd Formulation of agricultural chemicals
DE3246493A1 (de) 1982-12-16 1984-06-20 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von wasserdispergierbaren granulaten
EP0346789B1 (de) * 1988-06-16 1994-04-20 BASF Aktiengesellschaft Salicylsäurederivate und deren Schwefelanaloge
US5180587A (en) 1988-06-28 1993-01-19 E. I. Du Pont De Nemours And Company Tablet formulations of pesticides
EP0777964B1 (en) 1989-08-30 2001-11-14 Kynoch Agrochemicals (Proprietary) Limited Preparation of a dosage device
BR9106147A (pt) 1990-03-12 1993-03-09 Du Pont Granulos de pesticidas dispersaveis em agua ou soluveis em agua feitos a partir de ligantes termo-ativados
ES2091878T3 (es) 1990-10-11 1996-11-16 Sumitomo Chemical Co Composicion plaguicida.
TWI283164B (en) 2001-09-21 2007-07-01 Du Pont Anthranilamide arthropodicide treatment

Also Published As

Publication number Publication date
PE20170439A1 (es) 2017-05-09
IL249841A0 (en) 2017-03-30
ZA201700119B (en) 2018-08-29
JP2017522317A (ja) 2017-08-10
EP3169676A1 (en) 2017-05-24
WO2016010731A1 (en) 2016-01-21
CL2017000103A1 (es) 2017-08-18
US20170190671A1 (en) 2017-07-06
UY36210A (es) 2016-02-29
CO2017000337A2 (es) 2017-06-20
RU2017104513A3 (enExample) 2019-01-29
CA2954627A1 (en) 2016-01-21
CN106488913A (zh) 2017-03-08
KR20170032355A (ko) 2017-03-22
TW201625554A (zh) 2016-07-16
MX2017000594A (es) 2017-04-27
BR112017000745A2 (pt) 2017-11-14
SG11201700033YA (en) 2017-02-27
AU2015290153A1 (en) 2017-01-19

Similar Documents

Publication Publication Date Title
RU2017104513A (ru) Производные бис(арил)катехина в качестве гербицидов
RU2018104971A (ru) Арилоксипиримидиниловые эфиры в качестве гербицидов
JP2017522317A5 (enExample)
JP2018520122A5 (enExample)
JP2017504624A5 (enExample)
RU2017105221A (ru) Пиридоны в качестве гербицидов
JP6814846B2 (ja) ピリダジノン除草剤
DK1684583T3 (en) EMULSABLE CONCENTRATES CONTAINING ADJUVANCES
CN105916849B (zh) 作为除草剂的嘧啶氧基苯衍生物
RU2005115121A (ru) Комбинации арилоксифеноксипропионатов и средств защиты культур и их применение для повышения подавления сорной растительности
CN107531658B (zh) 作为除草剂的丁内酯
JP2009533448A5 (enExample)
CA2435761A1 (en) Herbicide-safener combination based on isoxazoline carboxylate safeners
EA201001177A1 (ru) Гербицидные комбинации, содержащие гербицид из класса диамино-s-триазинов
RU2018146743A (ru) Замещенные оксадиазолы для борьбы с фитопатогенными грибами
CA2717022A1 (en) Herbicidal compositions comprising pyroxasulfone v
JP4227418B2 (ja) イネ農作物に使用するためのベンゾイルシクロヘキサンジオン群からの除草剤を含む相乗作用除草剤
EA202191563A1 (ru) Гербицидные композиции
JP2004517154A5 (enExample)
JP2016512820A5 (enExample)
EA202191568A1 (ru) Гербицидные композиции
RU2015144280A (ru) Синергетическая борьба с сорняками путем нанесения фенокссулама и бензобициклона или кломазона и бензобициклона
RU2018136239A (ru) Гербициды
CN111315725B (zh) 作为除草剂的4-(3,4-二氢萘-1-基或2h-色烯-4-基)-5-羟基-2h-哒嗪-3-酮
RU2019138586A (ru) Пиримидинилоксибензо-конденсированные соединения в качестве гербицидов

Legal Events

Date Code Title Description
HZ9A Changing address for correspondence with an applicant
FA92 Acknowledgement of application withdrawn (lack of supplementary materials submitted)

Effective date: 20190514