DD156563A5 - Verfahren zur herstellung von pyridyliminomethylbenzolderivaten - Google Patents

Verfahren zur herstellung von pyridyliminomethylbenzolderivaten Download PDF

Info

Publication number: DD156563A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; hydrogen; alkoxy; formula; optionally
Prior art date: 1979-03-13

Application number

DD80227941A

Other languages

German (de)

English (en)

Inventor

Haken Pieter Ten

Shirley B Webb

Original Assignee

Shell Int Research

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.)

1979-03-13

Filing date

1980-03-11

Publication date

1982-09-08

1980-03-11 Application filed by Shell Int Research filed Critical Shell Int Research

1982-09-08 Publication of DD156563A5 publication Critical patent/DD156563A5/de

Links

238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 23
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
239000001257 hydrogen Substances 0.000 claims abstract description 17
238000000034 method Methods 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
-1 cyano, ethynyl Chemical group 0.000 claims abstract description 13
125000005843 halogen group Chemical group 0.000 claims abstract description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 10
125000004414 alkyl thio group Chemical class 0.000 claims abstract description 8
125000004104 aryloxy group Chemical group 0.000 claims abstract description 8
125000006413 ring segment Chemical group 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
125000004996 haloaryloxy group Chemical group 0.000 claims abstract description 6
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
125000005110 aryl thio group Chemical class 0.000 claims abstract description 4
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 3
125000005108 alkenylthio group Chemical class 0.000 claims abstract description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
125000005109 alkynylthio group Chemical class 0.000 claims abstract description 3
125000004659 aryl alkyl thio group Chemical group 0.000 claims abstract description 3
125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
125000005366 cycloalkylthio group Chemical class 0.000 claims abstract description 3
125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 3
125000005842 heteroatom Chemical group 0.000 claims abstract description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
239000001301 oxygen Chemical group 0.000 claims abstract description 3
125000005133 alkynyloxy group Chemical group 0.000 claims abstract 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 9
125000000547 substituted alkyl group Chemical group 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 7
CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000003282 alkyl amino group Chemical group 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000005415 substituted alkoxy group Chemical group 0.000 claims description 3
229910052783 alkali metal Chemical group 0.000 claims description 2
150000001340 alkali metals Chemical group 0.000 claims description 2
125000005122 aminoalkylamino group Chemical group 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
239000011593 sulfur Chemical group 0.000 claims description 2
229910052717 sulfur Chemical group 0.000 claims description 2
239000000203 mixture Substances 0.000 abstract description 8
125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
125000001188 haloalkyl group Chemical group 0.000 abstract description 2
239000000543 intermediate Substances 0.000 abstract description 2
230000000855 fungicidal effect Effects 0.000 abstract 2
239000005864 Sulphur Chemical group 0.000 abstract 1
150000002431 hydrogen Chemical group 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000012258 stirred mixture Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
150000002367 halogens Chemical group 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
TXPVUYLRHHHRLY-UHFFFAOYSA-N benzenecarboximidoyl chloride;hydrochloride Chemical compound Cl.ClC(=N)C1=CC=CC=C1 TXPVUYLRHHHRLY-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
ZHJOQLHRCOXPLV-UHFFFAOYSA-N 1-chloro-2-methylbenzene;hydrochloride Chemical compound Cl.CC1=CC=CC=C1Cl ZHJOQLHRCOXPLV-UHFFFAOYSA-N 0.000 description 1
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000004171 alkoxy aryl group Chemical group 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
ASCHNMXUWBEZDM-UHFFFAOYSA-N chloridodioxygen(.) Chemical compound [O]OCl ASCHNMXUWBEZDM-UHFFFAOYSA-N 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
239000000463 material Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
AFDMODCXODAXLC-UHFFFAOYSA-N phenylmethanimine Chemical compound N=CC1=CC=CC=C1 AFDMODCXODAXLC-UHFFFAOYSA-N 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
235000015096 spirit Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
238000001665 trituration Methods 0.000 description 1

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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- 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

Landscapes

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

DD80227941A 1979-03-13 1980-03-11 Verfahren zur herstellung von pyridyliminomethylbenzolderivaten DD156563A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7908822		1979-03-13

Publications (1)

Publication Number	Publication Date
DD156563A5 true DD156563A5 (de)	1982-09-08

Family

ID=10503839

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DD80219586A DD149452A5 (de)	1979-03-13	1980-03-11	Fungizide zusammensetzung
DD80227941A DD156563A5 (de)	1979-03-13	1980-03-11	Verfahren zur herstellung von pyridyliminomethylbenzolderivaten

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
DD80219586A DD149452A5 (de)	1979-03-13	1980-03-11	Fungizide zusammensetzung

Country Status (24)

Country	Link
EP (1)	EP0015628B1 (fr)
JP (1)	JPS55124764A (fr)
AT (1)	ATE11483T1 (fr)
AU (1)	AU533020B2 (fr)
BG (2)	BG31498A3 (fr)
BR (1)	BR8001433A (fr)
CA (1)	CA1160229A (fr)
DD (2)	DD149452A5 (fr)
DE (1)	DE3070045D1 (fr)
DK (1)	DK159423C (fr)
EG (1)	EG14257A (fr)
ES (1)	ES8104231A1 (fr)
HU (1)	HU185878B (fr)
IE (1)	IE49554B1 (fr)
IL (1)	IL59586A (fr)
IN (1)	IN153816B (fr)
MX (1)	MX5868E (fr)
NZ (1)	NZ193094A (fr)
OA (1)	OA06485A (fr)
PH (1)	PH17400A (fr)
PL (1)	PL121497B1 (fr)
SU (1)	SU1281153A3 (fr)
TR (1)	TR21441A (fr)
ZA (1)	ZA801413B (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4831044A (en) *	1987-10-29	1989-05-16	Ici Americas Inc.	Fungicidal pyridyl cyclopropane carboxamidines
US4994473A (en) *	1987-11-17	1991-02-19	Ici Americas Inc.	Pyridyl containing insecticides
GB8922691D0 (en) *	1989-10-09	1989-11-22	Ici Plc	Fungicides
EP0422848A1 (fr) *	1989-10-09	1991-04-17	Imperial Chemical Industries Plc	Fongicides
US5364943A (en) *	1991-11-27	1994-11-15	Pfizer Inc.	Preparation of substituted piperidines
JPH0794439B2 (ja) *	1990-05-31	1995-10-11	フアイザー・インコーポレイテツド	置換ピペリジンの製造法
GB9024873D0 (en) *	1990-11-15	1991-01-02	Ici Plc	Fungicidal compounds
ATE209186T1 (de) *	1992-05-18	2001-12-15	Pfizer	Überbrückte azabicyclische derivate als substanz p antagonisten
CA2141051A1 (fr) *	1992-08-04	1994-02-17	Terry J. Rosen	Derives de substitution d'heterocycles azotes
US8513286B2 (en) *	2007-02-22	2013-08-20	Syngenta Crop Protection Llc	Iminipyridine derivatives and their uses as microbiocides
EP2264012A1 (fr) *	2009-06-03	2010-12-22	Bayer CropScience AG	Hétéroarylamidine et son utilisation en tant que fongicide
EP2264011A1 (fr) *	2009-06-03	2010-12-22	Bayer CropScience AG	Hétéroarylamidine et son utilisation en tant que fongicide

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2472292A (en) *	1945-07-27	1949-06-07	Pyridium Corp	Benzylideneamino compounds of pyridine
NL100994C (fr) *	1956-07-04
FR1437425A (fr) *	1964-12-29	1966-05-06	Pechiney Progil Sa	Nouveaux produits fongicides à usage agricole dérivés de l'aldéhyde salicylique
US3472743A (en) *	1966-12-19	1969-10-14	Du Pont	Zinc plating baths and additives therefor
ZA775350B (en) *	1976-12-23	1978-07-26	Ciba Geigy Ag	Substituted 5-amino-2-pyridinecarboxylic acids
EP0000816A1 (fr) *	1977-08-06	1979-02-21	Beecham Group Plc	Dérivés substitués d'aminopyridines, leurs procédés de préparation et compositions pharmaceutiques les contenant

1980
- 1980-02-08 CA CA000345301A patent/CA1160229A/fr not_active Expired
- 1980-02-26 PH PH23692A patent/PH17400A/en unknown
- 1980-03-06 EP EP80200212A patent/EP0015628B1/fr not_active Expired
- 1980-03-06 DE DE8080200212T patent/DE3070045D1/de not_active Expired
- 1980-03-06 AT AT80200212T patent/ATE11483T1/de not_active IP Right Cessation
- 1980-03-11 TR TR21441A patent/TR21441A/xx unknown
- 1980-03-11 PL PL1980222598A patent/PL121497B1/pl unknown
- 1980-03-11 NZ NZ193094A patent/NZ193094A/xx unknown
- 1980-03-11 EG EG142/80A patent/EG14257A/xx active
- 1980-03-11 DD DD80219586A patent/DD149452A5/de not_active IP Right Cessation
- 1980-03-11 JP JP2985580A patent/JPS55124764A/ja active Granted
- 1980-03-11 AU AU56347/80A patent/AU533020B2/en not_active Ceased
- 1980-03-11 ZA ZA00801413A patent/ZA801413B/xx unknown
- 1980-03-11 BG BG049336A patent/BG31498A3/xx unknown
- 1980-03-11 BG BG046940A patent/BG31473A3/xx unknown
- 1980-03-11 HU HU80570A patent/HU185878B/hu not_active IP Right Cessation
- 1980-03-11 IL IL59586A patent/IL59586A/xx not_active IP Right Cessation
- 1980-03-11 BR BR8001433A patent/BR8001433A/pt not_active IP Right Cessation
- 1980-03-11 DK DK104980A patent/DK159423C/da not_active IP Right Cessation
- 1980-03-11 OA OA57050A patent/OA06485A/fr unknown
- 1980-03-11 DD DD80227941A patent/DD156563A5/de unknown
- 1980-03-11 MX MX808703U patent/MX5868E/es unknown
- 1980-03-11 SU SU802891905A patent/SU1281153A3/ru active
- 1980-03-11 IN IN176/DEL/80A patent/IN153816B/en unknown
- 1980-03-11 IE IE496/80A patent/IE49554B1/en not_active IP Right Cessation
- 1980-03-11 ES ES489421A patent/ES8104231A1/es not_active Expired

Also Published As

Publication number	Publication date
SU1281153A3 (ru)	1986-12-30
EP0015628A1 (fr)	1980-09-17
IL59586A0 (en)	1980-06-30
ES489421A0 (es)	1981-04-01
DK104980A (da)	1980-09-14
BR8001433A (pt)	1980-11-11
IE800496L (en)	1980-09-13
IL59586A (en)	1984-05-31
HU185878B (en)	1985-04-28
BG31473A3 (en)	1982-01-15
AU533020B2 (en)	1983-10-27
AU5634780A (en)	1980-09-18
OA06485A (fr)	1981-07-31
ATE11483T1 (de)	1985-02-15
DD149452A5 (de)	1981-07-15
DK159423C (da)	1991-03-18
MX5868E (es)	1984-08-15
ZA801413B (en)	1981-03-25
EG14257A (en)	1983-09-30
PH17400A (en)	1984-08-08
IN153816B (fr)	1984-08-18
NZ193094A (en)	1982-08-17
DK159423B (da)	1990-10-15
EP0015628B1 (fr)	1985-01-30
PL222598A1 (fr)	1980-12-15
CA1160229A (fr)	1984-01-10
IE49554B1 (en)	1985-10-30
ES8104231A1 (es)	1981-04-01
JPS6348866B2 (fr)	1988-09-30
PL121497B1 (en)	1982-05-31
TR21441A (tr)	1984-06-04
BG31498A3 (en)	1982-01-15
DE3070045D1 (en)	1985-03-14
JPS55124764A (en)	1980-09-26

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DD213348A5 (de)	1984-09-12	Fungizide zusammensetzung
DE2423536A1 (de)	1975-11-27	3-amino-phenylessigsaeure-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide
CH642352A5 (de)	1984-04-13	Maleinimid- und sukzinimid-derivate, verfahren zur herstellung derselben sowie herbizide enthaltend diese derivate.
DE2537571A1 (de)	1977-03-03	1,2-dialkyl-3,4,5-trisubstituierte- pyrazoliumsalze und verfahren zu ihrer herstellung
DD149452A5 (de)	1981-07-15	Fungizide zusammensetzung
DE2213958A1 (de)	1972-09-28	Substituierte 3-Benzylpyridine, ihre Herstellung und ihre Verwendung
DE3852506T2 (de)	1995-05-04	Verfahren zur Herstellung von Halogensulfonyl-substituierten Pyridinen.
CH632491A5 (de)	1982-10-15	Verfahren zur herstellung von mikrobiziden wirkstoffen und ihre verwendung.
CH620219A5 (fr)	1980-11-14
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