DD144914A5 - Verfahren zur herstellung von dicyanovinylhydrazonomalonitrilen - Google Patents

Verfahren zur herstellung von dicyanovinylhydrazonomalonitrilen Download PDF

Info

Publication number: DD144914A5
Authority: DD; German Democratic Republic
Prior art keywords: sydnone; tetracyanoethylene; reaction; melting point; malonitrile
Prior art date: 1977-02-14

Application number

DD78214507A

Other languages

German (de)

English (en)

Inventor

John E Franz

Original Assignee

Monsanto Co

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.)

1977-02-14

Filing date

1978-02-13

Publication date

1980-11-12

1978-02-13 Application filed by Monsanto Co filed Critical Monsanto Co

1980-11-12 Publication of DD144914A5 publication Critical patent/DD144914A5/de

Links

238000004519 manufacturing process Methods 0.000 title 1
NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 claims description 41
-1 o-Äthylphenyl-sydnon Chemical compound 0.000 claims description 35
238000006243 chemical reaction Methods 0.000 claims description 32
238000000034 method Methods 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 23
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical group ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 15
239000011541 reaction mixture Substances 0.000 claims description 9
NVRSPIKUPKOSIY-UHFFFAOYSA-N chembl1743348 Chemical compound CC=1N=NOC=1O NVRSPIKUPKOSIY-UHFFFAOYSA-N 0.000 claims description 8
AZUOSQWUWJITPO-UHFFFAOYSA-N 2-cyano-N-(2,2-dicyanoethenylamino)-2-hydroxyethanimidoyl cyanide Chemical compound C(#N)C(=CNN=C(C(C#N)O)C#N)C#N AZUOSQWUWJITPO-UHFFFAOYSA-N 0.000 claims description 4
VIOGMBRTOBOJKQ-UHFFFAOYSA-N 3-(4-fluorophenyl)oxadiazol-3-ium-5-olate Chemical compound O1C([O-])=C[N+](C=2C=CC(F)=CC=2)=N1 VIOGMBRTOBOJKQ-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 4
VUXSBVYENPHXGE-UHFFFAOYSA-N 3-(4-chlorophenyl)oxadiazol-3-ium-5-olate Chemical compound O1C([O-])=C[N+](C=2C=CC(Cl)=CC=2)=N1 VUXSBVYENPHXGE-UHFFFAOYSA-N 0.000 claims description 3
QTUKYTZKRWLELY-UHFFFAOYSA-N 3-(4-cyanophenyl)oxadiazol-3-ium-5-olate Chemical compound C(#N)C1=CC=C(C=C1)[N+]=1[N-]OC(C1)=O QTUKYTZKRWLELY-UHFFFAOYSA-N 0.000 claims description 3
KQEVEDHJIGSXDK-UHFFFAOYSA-N 3-phenyloxadiazol-3-ium-5-olate Chemical compound O1C([O-])=C[N+](C=2C=CC=CC=2)=N1 KQEVEDHJIGSXDK-UHFFFAOYSA-N 0.000 claims description 3
PTUVBAQXJHQVNN-UHFFFAOYSA-N C1=CC=C(C(=C1)C(F)(F)F)[N+]2=NOC(=C2)[O-] Chemical compound C1=CC=C(C(=C1)C(F)(F)F)[N+]2=NOC(=C2)[O-] PTUVBAQXJHQVNN-UHFFFAOYSA-N 0.000 claims description 3
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125000004093 cyano group Chemical group *C#N 0.000 claims description 3
RKAKVBXADCSTLE-UHFFFAOYSA-N 3-(4-nitrophenyl)oxadiazol-3-ium-5-olate Chemical compound O1C([O-])=C[N+](C=2C=CC(=CC=2)[N+]([O-])=O)=N1 RKAKVBXADCSTLE-UHFFFAOYSA-N 0.000 claims description 2
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XIIZHMNSBLVHKS-UHFFFAOYSA-N 3-(4-methylphenyl)oxadiazol-3-ium-5-olate Chemical compound C1=CC(C)=CC=C1[N+]1=NOC([O-])=C1 XIIZHMNSBLVHKS-UHFFFAOYSA-N 0.000 description 2
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238000003973 irrigation Methods 0.000 description 1
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
230000009935 nitrosation Effects 0.000 description 1
238000007034 nitrosation reaction Methods 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000003090 pesticide formulation Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229940072033 potash Drugs 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000000523 sample Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000002426 superphosphate Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
229940104261 taurate Drugs 0.000 description 1
150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000009105 vegetative growth Effects 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles

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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

DD78214507A 1977-02-14 1978-02-13 Verfahren zur herstellung von dicyanovinylhydrazonomalonitrilen DD144914A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/768,137 US4115104A (en)	1977-02-14	1977-02-14	Dicyanovinylhydrazonomalononitriles and the herbicidal use thereof

Publications (1)

Publication Number	Publication Date
DD144914A5 true DD144914A5 (de)	1980-11-12

Family

ID=25081645

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DD78214507A DD144914A5 (de)	1977-02-14	1978-02-13	Verfahren zur herstellung von dicyanovinylhydrazonomalonitrilen
DD78203679A DD136691A5 (de)	1977-02-14	1978-02-13	Phytotoxische zubereitung

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DD78203679A DD136691A5 (de)	1977-02-14	1978-02-13	Phytotoxische zubereitung

Country Status (23)

Country	Link
US (1)	US4115104A (cs)
JP (1)	JPS53121726A (cs)
AR (1)	AR221837A1 (cs)
AT (1)	AT352103B (cs)
AU (1)	AU3325178A (cs)
BE (1)	BE863901A (cs)
BG (2)	BG28985A3 (cs)
BR (1)	BR7800846A (cs)
CA (1)	CA1100997A (cs)
CS (1)	CS204018B2 (cs)
DD (2)	DD144914A5 (cs)
DE (1)	DE2805929A1 (cs)
DK (1)	DK63778A (cs)
FR (1)	FR2380255A1 (cs)
GB (1)	GB1575179A (cs)
IL (1)	IL54042A (cs)
IT (1)	IT1095406B (cs)
MY (1)	MY8400363A (cs)
NL (1)	NL7801544A (cs)
PL (2)	PL111777B1 (cs)
RO (1)	RO75613A (cs)
SU (2)	SU713524A3 (cs)
ZA (1)	ZA78834B (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2020169046A1 (zh) *	2019-02-22	2020-08-27	沈阳化工大学	一种1,1-二氰基腙类化合物作为农用杀细菌剂的应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3062635A (en) *	1958-07-18	1962-11-06	Du Pont	Method for inhibiting plant and fungal growth
US3138630A (en) *	1960-11-29	1964-06-23	American Cyanamid Co	Synthesis of beta-cyanovinyl hydrazines
US3755600A (en) *	1969-12-09	1973-08-28	Bayer Ag	N acyl dicyanocarbonyl phenyl hydrazones as arthropodicides and fungicides
US3914279A (en) *	1972-02-25	1975-10-21	Du Pont	Aminomethyleneaminomaleonitriles
GB1441589A (en) *	1972-10-06	1976-07-07	Fisons Ltd	Aminomethylenemalonitriles and their use as fungicides

1977
- 1977-02-14 US US05/768,137 patent/US4115104A/en not_active Expired - Lifetime
1978
- 1978-02-10 NL NL7801544A patent/NL7801544A/xx not_active Application Discontinuation
- 1978-02-13 DK DK63778A patent/DK63778A/da not_active Application Discontinuation
- 1978-02-13 BG BG038666A patent/BG28985A3/xx unknown
- 1978-02-13 AT AT99178A patent/AT352103B/de not_active IP Right Cessation
- 1978-02-13 AR AR271080A patent/AR221837A1/es active
- 1978-02-13 DE DE19782805929 patent/DE2805929A1/de not_active Withdrawn
- 1978-02-13 IT IT20235/78A patent/IT1095406B/it active
- 1978-02-13 CA CA297,073A patent/CA1100997A/en not_active Expired
- 1978-02-13 SU SU782578337A patent/SU713524A3/ru active
- 1978-02-13 AU AU33251/78A patent/AU3325178A/en active Pending
- 1978-02-13 DD DD78214507A patent/DD144914A5/de unknown
- 1978-02-13 FR FR7804006A patent/FR2380255A1/fr active Granted
- 1978-02-13 BR BR7800846A patent/BR7800846A/pt unknown
- 1978-02-13 GB GB5652/78A patent/GB1575179A/en not_active Expired
- 1978-02-13 PL PL1978204593A patent/PL111777B1/pl unknown
- 1978-02-13 CS CS78900A patent/CS204018B2/cs unknown
- 1978-02-13 ZA ZA00780834A patent/ZA78834B/xx unknown
- 1978-02-13 RO RO7893193A patent/RO75613A/ro unknown
- 1978-02-13 BG BG040117A patent/BG28976A4/xx unknown
- 1978-02-13 JP JP1420078A patent/JPS53121726A/ja active Pending
- 1978-02-13 PL PL1978215719A patent/PL110773B1/pl unknown
- 1978-02-13 BE BE185115A patent/BE863901A/xx unknown
- 1978-02-13 DD DD78203679A patent/DD136691A5/xx unknown
- 1978-02-13 IL IL54042A patent/IL54042A/xx unknown
- 1978-06-28 SU SU782630806A patent/SU799654A3/ru active
1984
- 1984-12-30 MY MY363/84A patent/MY8400363A/xx unknown

Also Published As

Publication number	Publication date
SU713524A3 (ru)	1980-01-30
PL110773B1 (en)	1980-07-31
ATA99178A (de)	1979-02-15
BG28976A4 (en)	1980-08-15
AU3325178A (en)	1979-08-23
BE863901A (fr)	1978-08-14
SU799654A3 (ru)	1981-01-23
IT1095406B (it)	1985-08-10
AT352103B (de)	1979-09-10
CA1100997A (en)	1981-05-12
DE2805929A1 (de)	1978-08-17
PL111777B1 (en)	1980-09-30
IL54042A0 (en)	1978-04-30
JPS53121726A (en)	1978-10-24
DK63778A (da)	1978-08-15
IT7820235A0 (it)	1978-02-13
MY8400363A (en)	1984-12-31
US4115104A (en)	1978-09-19
ZA78834B (en)	1979-01-31
AR221837A1 (es)	1981-03-31
RO75613A (ro)	1980-11-30
CS204018B2 (en)	1981-03-31
BR7800846A (pt)	1979-01-02
FR2380255A1 (fr)	1978-09-08
GB1575179A (en)	1980-09-17
IL54042A (en)	1981-10-30
NL7801544A (nl)	1978-08-16
PL204593A1 (pl)	1979-04-09
FR2380255B1 (cs)	1981-07-31
BG28985A3 (en)	1980-08-15
DD136691A5 (de)	1979-07-25

Publication	Publication Date	Title
DE2040579A1 (de)	1971-02-25	Neue Thiophenderivate
DD152712A5 (de)	1981-12-09	Herbizides mittel
DD202375A5 (de)	1983-09-14	Herbizide mittel
DE2735841A1 (de)	1978-02-16	3,4-dimethyl-2-hydroxy-5-oxo-2,5- dihydro-pyrrol-verbindungen, verfahren zu deren herstellung und schaedlingsbekaempfungsmittel
CH617833A5 (cs)	1980-06-30
DE1542943A1 (de)	1972-04-06	Herbizide
DE2118935A1 (de)	1971-11-04	Neue substituierte Isoxazolpyrimidine und diese Verbindungen enthaltende herbicide Zusammensetzungen
DE2720792A1 (de)	1977-11-24	Triazolotriazinderivate, verfahren zur herstellung derselben und diese enthaltende herbizide mittel sowie unkrautbekaempfungsverfahren
DE2040580A1 (de)	1971-04-22	Thiazolderivate
DE1922837A1 (de)	1969-11-20	Neue Pyrido[1,2-a]-s-triazin-dione
DE1914012C3 (de)	1982-04-22	2-Amino-4-azido-6-cyclopropylamino-s-triazin-Derivate
DD218828A5 (de)	1985-02-20	Herbizide zusammensetzung
DD144914A5 (de)	1980-11-12	Verfahren zur herstellung von dicyanovinylhydrazonomalonitrilen
EP0153601B1 (de)	1987-04-01	2-Alkoxyaminosulfonylbenzolsulfonyl-harnstoff-Derivate
DE2536149C3 (de)	1979-07-12	N-Phosphonomethylglycinphenyl- ' hydrazide und Verfahren zu ihrer Herstellung
AT358324B (de)	1980-09-10	Phytotoxische zubereitung
EP0108908A2 (de)	1984-05-23	Neue Benzotriazole, ihre Herstellung und ihre Verwendung als biozide Wirkstoffe
DE1567016A1 (de)	1970-04-16	Heterocyclische Verbindungen und ihre Anwendung
DE69002260T2 (de)	1994-02-17	4-Ethyl-3-(substituiertes-phenyl)-1-(3-trifluormethyl-phenyl)-2-pyrrolidinon-Derivate, Herstellungsverfahren und Anwendung sowie diese Verbindungen enthaltende herbizide Mittel.
DE1567150A1 (de)	1970-08-27	Selektives Herbizid
DE2226593B2 (de)	1977-09-01	Halogenacetanilid-derivate und diese enthaltende herbicide zubereitungen
DD151867A5 (de)	1981-11-11	Formulierung fuer landwirtschaftliche zwecke
DD250452A5 (de)	1987-10-14	Unkrautbekaempfungsmittel
EP0097614A2 (de)	1984-01-04	Schädlingsbekämpfungsmittel
DE2160912C3 (de)	1977-03-03	3-Phenylhydantoine, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide