DE57473T1 - Verfahren zur herstellung von trifluoromethylpyridil(oxy/thio)phenoxypropion-verbindungen, insbesonders wirksam wie herbizide. - Google Patents
Verfahren zur herstellung von trifluoromethylpyridil(oxy/thio)phenoxypropion-verbindungen, insbesonders wirksam wie herbizide.Info
- Publication number
- DE57473T1 DE57473T1 DE198278100291T DE82101502T DE57473T1 DE 57473 T1 DE57473 T1 DE 57473T1 DE 198278100291 T DE198278100291 T DE 198278100291T DE 82101502 T DE82101502 T DE 82101502T DE 57473 T1 DE57473 T1 DE 57473T1
- Authority
- DE
- Germany
- Prior art keywords
- phenol
- trifluoromethyl
- thio
- oxy
- alkyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
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)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (4)
1. Verfahren zu Herstellung von Trifluormethylpyridyl~
(Oxy/Thio)-Phenoxypropion-Verbindungen, insbesondere
wirksam als Herbicide zur Kontrolle von grasartigen oder getreideartigen Unkräutern mit der all-.
gemeinen Formel I
(D
worin T Sauerstoff oder Schwefel ist;
X Cl, Br oder CF ist;
YH, Cl, Br oder CF ist, vorausgesetzt, daß
mindestens ein X oder Y CF ist; Z -C-OR, -CNR1R2, -C-ODM®, -CN, -CH
-CH2OCR4, oder -CSR5 ist;
M^NHR1R1R1, Na, K, Mg oder Ca ist;
R H, eine C.g-Alkyl-, Benzyl-, Chlorbenzyl-,
oder C,_fi-Alkoxyalkylgruppe ist; R1 H, C, ^-Alkyl,- oder C3-3 Hydroxyalkylgruppe
ist;
R2 R1 oder -OCH3 ist;
R_ H oder C1-.-Alkyl ist;
R. eine C1_7~Alkylgruppe ist und
Rc eine C. _.-Alkylgruppe ist, wie in der veröffentlichten
europäischen Patentanmeldung Nr. 0 000 beschrieben,
dadurch gekennzeichnet , daß man als Zwischenprodukt ein Trifluormethylpyridyl-(Oxy/Thio)-Phenol
mit der allgemeinen Formel II verwendet, ·■■:.·
worin T Sauerstoff oder Schwefel ist; und
worin T Sauerstoff oder Schwefel ist; und
Y H oder Cl ist und M Wasserstoff oder das Kation einer Lauge ist.
(ID
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet , daß man als Zwischenprodukt
4-(5-Trifluormethyl-2-Pyridyloxy)Phenol,
4- (5-Trifluormethyl-2-Pyridylthio)Phenol, 4-(3-Chlor-5-Trifluormethyl-2-Pyridylthio)Phenol oder
4-(3-Chlor-5-Trifluormethyl-2-Pyridyloxy)Phenol verwendet.
3. Verfahren nach einem der Ansprüche 1 oder 2, dadurch gekennzeichnet,
daß das Zwischenprodukt mit einem Propansäureester reagiert und daß man ggf. das erhaltene Produkt in
das gewünschte Derivat mit der Formel (I) umwandelt.
4. Verfahren nach Anspruch 3, dadurch gekennzeichnet , daß man das Zwischenprodukt in einem Lösungsmittel
auflöst, wasserfreies, pulverförmiges Natriumhydroxid
dazugibt und damit reagieren läßt, daß man Propansäureester zu der Reaktionsmischung zugibt, daß man einige
Zeit bei etwa 1000C rührt und das erhaltene Produkt
isoliert.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US81794377A | 1977-07-22 | 1977-07-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE57473T1 true DE57473T1 (de) | 1983-08-04 |
Family
ID=25224264
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE7878100291T Expired DE2861155D1 (en) | 1977-07-22 | 1978-06-30 | Trifluoromethyl pyridinyl(oxy/thio)phenoxy propanoic acids and propanols and derivatives thereof |
DE198278100291T Pending DE57473T1 (de) | 1977-07-22 | 1978-06-30 | Verfahren zur herstellung von trifluoromethylpyridil(oxy/thio)phenoxypropion-verbindungen, insbesonders wirksam wie herbizide. |
DE8080101361T Expired DE2862194D1 (de) | 1977-07-22 | 1978-06-30 | Trifluoromethyl pyridinyl(oxy/thio)phenols |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE7878100291T Expired DE2861155D1 (en) | 1977-07-22 | 1978-06-30 | Trifluoromethyl pyridinyl(oxy/thio)phenoxy propanoic acids and propanols and derivatives thereof |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE8080101361T Expired DE2862194D1 (de) | 1977-07-22 | 1978-06-30 | Trifluoromethyl pyridinyl(oxy/thio)phenols |
Country Status (13)
Country | Link |
---|---|
US (1) | US4551170A (de) |
EP (3) | EP0017767B1 (de) |
JP (14) | JPS5424879A (de) |
AR (1) | AR227618A1 (de) |
AU (2) | AU519094B2 (de) |
BR (2) | BR7804724A (de) |
CA (2) | CA1247625A (de) |
DE (3) | DE2861155D1 (de) |
DK (1) | DK156830C (de) |
HK (1) | HK12182A (de) |
MY (1) | MY8500039A (de) |
NL (1) | NL971019I1 (de) |
NZ (1) | NZ187756A (de) |
Families Citing this family (55)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
UA6300A1 (uk) * | 1977-07-21 | 1994-12-29 | Ісіхара Сангіо Кайся Лтд | Гербіцидний склад |
TR19824A (tr) * | 1977-07-21 | 1980-01-24 | Ishihara Sangyo Kaisha | Trilorometilpiridoksifenoksipropionik as tuerevleri ve bunlari ihtiva eden herbisidler |
JPS54119476A (en) * | 1978-03-10 | 1979-09-17 | Ishihara Sangyo Kaisha Ltd | 4-(5-fluoromethyl-2-pyridyloxy)phenoxyalkanecarbocyic acid derivatives and their preparation |
CA1247625A (en) | 1977-07-22 | 1988-12-28 | Howard Johnston | Trifluoromethyl pyridinyloxyphenoxy propanoic acids and propanols and derivatives thereof and methods of herbicidal use |
DE2862490D1 (en) * | 1977-08-12 | 1988-04-21 | Ici Plc | Phenoxypyridine compound |
ZA784334B (en) * | 1977-08-12 | 1979-07-25 | Ici Ltd | Herbicidal pyridine compounds |
JPS5461182A (en) * | 1977-10-20 | 1979-05-17 | Ishihara Sangyo Kaisha Ltd | 2-phenoxy-5-trifluoromethylpyridine compounds |
JPS5461183A (en) * | 1977-10-21 | 1979-05-17 | Ishihara Sangyo Kaisha Ltd | 2-substituted-5-trifluoromethyl pyridine compounds |
DE2755536A1 (de) * | 1977-12-13 | 1979-06-21 | Ciba Geigy Ag | Neue herbizid und pflanzenregulatorisch wirksame pyridyloxy-phenoxy-propionsaeurederivate |
CH650493A5 (en) * | 1977-12-24 | 1985-07-31 | Hoechst Ag | D-(+)-alpha-phenoxypropionic acid derivatives |
JPS5492970A (en) * | 1977-12-29 | 1979-07-23 | Ciba Geigy Ag | Pyridyloxyyphenoxyypropionic acid derivative* its manufacture and herbicide or plant growth regulating composition |
EP0003877B1 (de) * | 1978-02-15 | 1988-02-03 | Imperial Chemical Industries Plc | Herbizide 2-(4(2-Pyridyloxy)Phenoxy)Propanderivate, Verfahren zu deren Herstellung, und diese enthaltende herbizide Zusammensetzungen |
EP0003890B2 (de) * | 1978-03-01 | 1990-04-04 | Imperial Chemical Industries Plc | Herbizide Pyridinverbindungen und sie enthaltende herbizide Zusammensetzungen |
DE2967486D1 (en) * | 1978-03-01 | 1985-08-29 | Ici Plc | Mixtures of herbicidal pyridyloxyphenoxypropanoic acid derivatives with other herbicides, and processes of killing unwanted plants therewith |
JPS54132433U (de) * | 1978-03-03 | 1979-09-13 | ||
EP0004433B1 (de) * | 1978-03-17 | 1983-05-18 | Imperial Chemical Industries Plc | Herbizid wirksame 2-(p-substituierte-Phenoxy)-pyridine und Verfahren zu deren Herstellung |
JPS54144375A (en) * | 1978-04-27 | 1979-11-10 | Ishihara Sangyo Kaisha Ltd | 4-(5-trifluoromethyl-2-pyridyloxy)phenoxyalkane derivative and herbicide containing the same |
EP0006608B1 (de) * | 1978-06-29 | 1982-06-30 | Ciba-Geigy Ag | Herbizid wirksame, optisch aktive R(+)-Dichlorpyridyloxy-alpha-phenoxy-propionsäure-propargylester, Verfahren zu ihrer Herstellung und deren Verwendung in Mitteln zur Unkrautbekämpfung |
DD151037A5 (de) * | 1978-07-03 | 1981-09-30 | Ciba Geigy Ag | Herbizides und das pflanzenwachstum regulierendes mittel |
US4309210A (en) * | 1978-12-01 | 1982-01-05 | Ciba-Geigy Corporation | Preemergence method of selectively controlling weeds in crops of cereals and composition therefor |
JPS55116060U (de) * | 1979-02-08 | 1980-08-15 | ||
NZ192948A (en) * | 1979-03-09 | 1982-02-23 | Ishihara Sangyo Kaisha | Preparation of beta-trifuloromethyl-pyridine derivatives directly from beta-picoline |
US4266064A (en) * | 1979-03-19 | 1981-05-05 | Ishihara Sangyo Kaisha Ltd. | Process for producing chloro β-trifluoromethylpyridines |
JPS55149114U (de) * | 1979-04-13 | 1980-10-27 | ||
EP0021613B1 (de) * | 1979-06-20 | 1983-04-06 | Imperial Chemical Industries Plc | Pyridin-Derivate, Verfahren zu ihrer Herstellung, herbizide Zusammensetzungen, die sie enthalten, und Verfahren zur Pflanzenvertilgung mit Hilfe dieser Derivate |
NZ194612A (en) * | 1979-08-31 | 1982-12-21 | Ici Australia Ltd | Benzotriazine derivatives intermediates and herbicidal compositions |
AU535258B2 (en) * | 1979-08-31 | 1984-03-08 | Ici Australia Limited | Benzotriazines |
AU541697B2 (en) * | 1979-11-19 | 1985-01-17 | Ici Australia Limited | Quinoline derivatives |
CA1317299C (en) * | 1980-06-23 | 1993-05-04 | Maged Mohamed Fawzi | Quinoxalinyloxy ethers as selective weed control agents |
JPS57501028A (de) * | 1980-07-30 | 1982-06-10 | ||
JPH0234932B2 (ja) * | 1980-08-26 | 1990-08-07 | Ici Australia Ltd | Ariiruokishudotainogoseihoho |
ZA828142B (en) * | 1981-11-16 | 1984-06-27 | Dow Chemical Co | Inhibiting the antagonism between pyridyloxy-phenoxyalkanoate herbicides and benzothiadiazinone herbicides in post-emergent applications |
DE3151589A1 (de) * | 1981-12-28 | 1983-07-07 | Basf Ag, 6700 Ludwigshafen | Diether von m- oder p-hydroxyphenolen und verfahren zur herstellung der diether oder monoether von m- oder p-hydroxyphenolen |
US4505743A (en) * | 1981-12-31 | 1985-03-19 | Ciba-Geigy Corporation | α-[4-(3-Fluoro-5'-halopyridyl-2'-oxy)-phenoxy]-propionic acid derivatives having herbicidal activity |
IL68822A (en) * | 1982-06-18 | 1990-07-12 | Dow Chemical Co | Pyridyl(oxy/thio)phenoxy compounds,herbicidal compositions and methods of using them |
DE3242487A1 (de) * | 1982-11-18 | 1984-05-24 | Hoechst Ag, 6230 Frankfurt | Herbizide mittel |
HU188235B (en) * | 1982-12-11 | 1986-03-28 | Alkaloida Vegyeszeti Gyar,Hu | Process for producing fluoro-methyl-quinoline derivatives |
ZA848416B (en) * | 1983-11-10 | 1986-06-25 | Dow Chemical Co | Fluorophenoxy compounds,herbicidal compositions and methods |
EP0200677B1 (de) * | 1985-04-01 | 1991-04-03 | Ciba-Geigy Ag | 3-Fluorpyridyl-2-oxy-phenoxy-Derivate mit herbizider Wirkung |
JPS62267275A (ja) * | 1986-05-16 | 1987-11-19 | Aguro Kanesho Kk | プロピオン酸チオ−ルエステル誘導体 |
JPS61280476A (ja) * | 1986-06-06 | 1986-12-11 | Ishihara Sangyo Kaisha Ltd | 2−フエノキシ−5−トリフルオロメチルピリジン系化合物 |
JPS61280477A (ja) * | 1986-06-06 | 1986-12-11 | Ishihara Sangyo Kaisha Ltd | 4−(5−フルオロメチル−2−ピリジルオキシ)フエノキシアルカンカルボン酸およびその誘導体 |
JPS6263573A (ja) * | 1986-08-15 | 1987-03-20 | Ishihara Sangyo Kaisha Ltd | トリフルオロメチルピリドキシフエノキシプロピオン酸またはその誘導体 |
JPS6370851U (de) * | 1986-10-28 | 1988-05-12 | ||
JPH0321878Y2 (de) * | 1986-10-28 | 1991-05-13 | ||
JPH0321883Y2 (de) * | 1986-10-31 | 1991-05-13 | ||
US5205855A (en) * | 1987-08-11 | 1993-04-27 | Suntory Limited | Herbicidally active phenoxyalkanecarboxylic acid derivatives |
US5068336A (en) * | 1989-02-27 | 1991-11-26 | Tosoh Corporation | Process for producing 2-(4'-hydroxphenoxy)-3-chloro-5-trifluoromethylpyridine |
HU208311B (en) * | 1989-11-02 | 1993-09-28 | Alkaloida Vegyeszeti Gyar | Resolving process for producing enantiomers of 2-/4-(5-trifluoromethyl-2-pyridyloxy)-phenoxy/-propanoic acid |
DE4234637A1 (de) * | 1992-10-14 | 1994-04-21 | Bayer Ag | Verfahren zur Herstellung von 2-substituierten 5-Alkyl-pyridinen |
US5475131A (en) * | 1993-01-19 | 1995-12-12 | Bayer Aktiengesellschaft | Process for the preparation of a mixture of aminomethylenated glutaconic acid dinitriles |
WO2003068744A1 (fr) * | 2002-02-18 | 2003-08-21 | Ishihara Sangyo Kaisha, Ltd. | Derives de la pyridine ou leurs sels, et inhibiteurs de production de citokine renfermant ces derives |
CN106397309A (zh) * | 2016-08-31 | 2017-02-15 | 南京红太阳生物化学有限责任公司 | 一种2,3‑二氯‑5‑三氟甲基吡啶的合成方法 |
CN112236654A (zh) | 2018-05-03 | 2021-01-15 | 耐普罗公司 | 用于提供内容物量监视器的装置、系统和方法 |
US20210072067A1 (en) | 2018-05-03 | 2021-03-11 | Nypro Inc. | Apparatus, system, and method of providing a solids level monitor |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3711486A (en) * | 1969-03-17 | 1973-01-16 | Dow Chemical Co | Substituted(trifluoromethyl)pyridines |
US3832383A (en) * | 1971-06-01 | 1974-08-27 | Monsanto Co | Herbicidal acyloxyalkyl anilides |
US3928416A (en) * | 1972-03-14 | 1975-12-23 | Rohm & Haas | Herbicidal 4-trifluoromethyl-4{40 nitrodiphenyl ethers |
US3967949A (en) * | 1973-06-18 | 1976-07-06 | Eli Lilly And Company | Fluoroalkoxyphenyl-substituted nitrogen heterocycles as plant stunting agents |
US3931201A (en) * | 1974-01-22 | 1976-01-06 | The Dow Chemical Company | Substituted pyridinyloxy(thio)phenyl -acetamides, -ureas and urea derivatives |
CS185694B2 (en) * | 1974-07-17 | 1978-10-31 | Ishihara Sangyo Kaisha | Herbicidal agent |
DK154074C (da) * | 1974-10-17 | 1989-02-27 | Ishihara Sangyo Kaisha | Alfa-(4-(5 eller 3,5 substitueret pyridyl-2-oxy)-phenoxy)-alkan-carboxylsyrer eller derivater deraf til anvendelse som herbicider, herbicidt middel samt fremgangsmaader til bekaempelse af ukrudt |
JPS51142537A (en) * | 1975-05-30 | 1976-12-08 | Ishihara Sangyo Kaisha Ltd | A herbicide |
JPS6025401B2 (ja) * | 1975-10-29 | 1985-06-18 | 石原産業株式会社 | 除草剤 |
GB1512189A (en) * | 1975-10-29 | 1978-05-24 | Ishihara Mining & Chemical Co | Herbicidal composition and method of use thereof |
NL7612668A (nl) * | 1976-01-06 | 1977-07-08 | Dow Chemical Co | Werkwijze voor het bereiden van nieuwe organo- fosforusverbindingen. |
JPS52131540A (en) * | 1976-04-14 | 1977-11-04 | Ishihara Sangyo Kaisha Ltd | Phenoxyvaleric acid derivatives and herbicides therefrom |
US4133675A (en) * | 1976-07-23 | 1979-01-09 | Ciba-Geigy Corporation | Pyridyloxy-phenoxy-alkanecarboxylic acid derivatives which are effective as herbicides and as agents regulating plant growth |
JPS54119476A (en) * | 1978-03-10 | 1979-09-17 | Ishihara Sangyo Kaisha Ltd | 4-(5-fluoromethyl-2-pyridyloxy)phenoxyalkanecarbocyic acid derivatives and their preparation |
TR19824A (tr) * | 1977-07-21 | 1980-01-24 | Ishihara Sangyo Kaisha | Trilorometilpiridoksifenoksipropionik as tuerevleri ve bunlari ihtiva eden herbisidler |
CA1247625A (en) * | 1977-07-22 | 1988-12-28 | Howard Johnston | Trifluoromethyl pyridinyloxyphenoxy propanoic acids and propanols and derivatives thereof and methods of herbicidal use |
DE2862490D1 (en) * | 1977-08-12 | 1988-04-21 | Ici Plc | Phenoxypyridine compound |
JPS5461182A (en) * | 1977-10-20 | 1979-05-17 | Ishihara Sangyo Kaisha Ltd | 2-phenoxy-5-trifluoromethylpyridine compounds |
EP0003877B1 (de) * | 1978-02-15 | 1988-02-03 | Imperial Chemical Industries Plc | Herbizide 2-(4(2-Pyridyloxy)Phenoxy)Propanderivate, Verfahren zu deren Herstellung, und diese enthaltende herbizide Zusammensetzungen |
EP0003648A3 (de) * | 1978-02-15 | 1979-09-05 | Imperial Chemical Industries Plc | Herbizide 4-Aryloxy-phenoxypropionamidderivate, diese Derivate enthaltende Zusammensetzungen und Verfahren zu ihrer Herstellung |
EP0003890B2 (de) * | 1978-03-01 | 1990-04-04 | Imperial Chemical Industries Plc | Herbizide Pyridinverbindungen und sie enthaltende herbizide Zusammensetzungen |
DE2967486D1 (en) * | 1978-03-01 | 1985-08-29 | Ici Plc | Mixtures of herbicidal pyridyloxyphenoxypropanoic acid derivatives with other herbicides, and processes of killing unwanted plants therewith |
EP0004433B1 (de) * | 1978-03-17 | 1983-05-18 | Imperial Chemical Industries Plc | Herbizid wirksame 2-(p-substituierte-Phenoxy)-pyridine und Verfahren zu deren Herstellung |
JPS54144375A (en) * | 1978-04-27 | 1979-11-10 | Ishihara Sangyo Kaisha Ltd | 4-(5-trifluoromethyl-2-pyridyloxy)phenoxyalkane derivative and herbicide containing the same |
-
1978
- 1978-06-21 CA CA000305900A patent/CA1247625A/en not_active Expired
- 1978-06-30 EP EP80101361A patent/EP0017767B1/de not_active Expired
- 1978-06-30 EP EP82101502A patent/EP0057473A3/de not_active Ceased
- 1978-06-30 DE DE7878100291T patent/DE2861155D1/de not_active Expired
- 1978-06-30 EP EP78100291A patent/EP0000483B1/de not_active Expired
- 1978-06-30 DE DE198278100291T patent/DE57473T1/de active Pending
- 1978-06-30 DE DE8080101361T patent/DE2862194D1/de not_active Expired
- 1978-07-03 NZ NZ187756A patent/NZ187756A/xx unknown
- 1978-07-03 AU AU37703/78A patent/AU519094B2/en not_active Expired
- 1978-07-20 AR AR273020A patent/AR227618A1/es active
- 1978-07-21 DK DK326078A patent/DK156830C/da not_active IP Right Cessation
- 1978-07-21 JP JP8928778A patent/JPS5424879A/ja active Granted
- 1978-07-21 BR BR7804724A patent/BR7804724A/pt unknown
- 1978-07-21 BR BR7804725A patent/BR7804725A/pt unknown
-
1980
- 1980-10-08 JP JP14111180A patent/JPS56123971A/ja active Granted
-
1981
- 1981-10-23 CA CA000388668A patent/CA1321590C/en not_active Expired - Lifetime
-
1982
- 1982-03-18 HK HK121/82A patent/HK12182A/xx not_active IP Right Cessation
- 1982-10-01 JP JP57173144A patent/JPS5883675A/ja active Pending
- 1982-10-01 JP JP57173142A patent/JPS5899464A/ja active Pending
- 1982-10-01 JP JP57173143A patent/JPS5890553A/ja active Granted
-
1983
- 1983-04-15 JP JP58066813A patent/JPS58201766A/ja active Pending
- 1983-07-15 JP JP58129296A patent/JPS5962568A/ja active Pending
- 1983-07-15 JP JP58129293A patent/JPS5962567A/ja active Pending
- 1983-07-15 JP JP58129292A patent/JPS5967202A/ja active Granted
- 1983-07-15 JP JP58129294A patent/JPS5967267A/ja active Granted
- 1983-07-15 JP JP58129295A patent/JPS5967268A/ja active Granted
- 1983-08-12 JP JP58147929A patent/JPS59130271A/ja active Pending
- 1983-08-12 AU AU17941/83A patent/AU568503B2/en not_active Expired
-
1984
- 1984-12-10 US US06/679,976 patent/US4551170A/en not_active Expired - Fee Related
-
1985
- 1985-09-19 JP JP60207714A patent/JPS61106503A/ja active Granted
- 1985-12-30 MY MY39/85A patent/MY8500039A/xx unknown
-
1987
- 1987-08-19 JP JP62206201A patent/JPS63152302A/ja active Granted
-
1997
- 1997-07-23 NL NL971019C patent/NL971019I1/nl unknown
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