FR2323683A1 - Phytohormonal and herbicidal amidoxime derivs. - prepd. by treatment of an imino ether with an O-amino oxy-acetate - Google Patents
Phytohormonal and herbicidal amidoxime derivs. - prepd. by treatment of an imino ether with an O-amino oxy-acetateInfo
- Publication number
- FR2323683A1 FR2323683A1 FR7527884A FR7527884A FR2323683A1 FR 2323683 A1 FR2323683 A1 FR 2323683A1 FR 7527884 A FR7527884 A FR 7527884A FR 7527884 A FR7527884 A FR 7527884A FR 2323683 A1 FR2323683 A1 FR 2323683A1
- Authority
- FR
- France
- Prior art keywords
- alkyl
- phenyl
- alkoxy
- substd
- ethyl
- 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.)
- Granted
Links
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 title abstract 2
- 230000002363 herbicidal effect Effects 0.000 title 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 abstract 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- IJMOMMSECUQUFV-UHFFFAOYSA-N ethyl thiophene-2-carboximidate Chemical compound CCOC(=N)C1=CC=CS1 IJMOMMSECUQUFV-UHFFFAOYSA-N 0.000 abstract 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 abstract 1
- 241001233957 eudicotyledons Species 0.000 abstract 1
- 230000005089 fruit drop Effects 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 239000002184 metal Chemical group 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- -1 sulphamoyl Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/18—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Amidoxime derivs. of formula Ar-C(NH2)NOCHRCOOR1 (I) are new (where R = H, 1-4C alkyl or phenyl; R1 = H, 1-4C alkyl, or a metal atom; Ar = phenyl substd. by 1-3 of halogens, alkyl, OH, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, CF3 CF3O,CF3S, carboxy, alkoxycarbonyl, NO2 NH2, alkylamino, dialkylamino, acylamino, alkoxycarbonylamino, azido, alkanoyl, sulphamoyl which may be substd. on the N by 1 or 2 alkyl groups or phenyl, or Ar = 5 membered aromatic heterocycle contg. O,N or S opt. substd. by halogen, alkyl, alkoxy, alkylthio or phenyl alkyl; the alkyl, alkoxy, and acyl groups contain up to 4C atoms). At concn. of 1-100g (I)/hl of water, the cpds. have phytohormonal activity and aid fruiting of certain plants, prevent leaf and fruit drop, and increase root formation, At application rates of 0.5-10 kg/ha. the cpds. are pre- and post emergence herbicides esp. useful against dicotyledons. A typical cpd. is (I; Ar = 2-thienyl, R1 = ethyl; R = H). This was prepd. from ethyl 2-thiophene carboximidate HCl and ethyl amino oxyacetate HCl in pyridine.
Priority Applications (29)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7527884A FR2323683A1 (en) | 1975-09-11 | 1975-09-11 | Phytohormonal and herbicidal amidoxime derivs. - prepd. by treatment of an imino ether with an O-amino oxy-acetate |
| CA260,741A CA1080234A (en) | 1975-09-11 | 1976-09-08 | Derivatives of amidoximes |
| DE19762640484 DE2640484A1 (en) | 1975-09-11 | 1976-09-08 | AMIDOXIM DERIVATIVES, THEIR PRODUCTION AND USE |
| DD7600194681A DD128918A5 (en) | 1975-09-11 | 1976-09-08 | PHYTHOHORMONAL AND HERBICIDAL COMPOSITIONS |
| IE2008/76A IE43624B1 (en) | 1975-09-11 | 1976-09-08 | New derivatives of amidoximes |
| GB37229/76A GB1501529A (en) | 1975-09-11 | 1976-09-08 | Derivatives of amidoximes |
| BR7605959A BR7605959A (en) | 1975-09-11 | 1976-09-10 | PROCESS OF PREPARATION OF NEW AMIDOXIM DERIVATIVES AND THEIR APPLICATIONS |
| HU76PI539A HU176860B (en) | 1975-09-11 | 1976-09-10 | Preparation containing amide-oxime derivative with plant hormone and herbicide activity and process for preparing the active materials |
| US05/722,215 US4116974A (en) | 1975-09-11 | 1976-09-10 | Herbicidal and phytohormonal amidoximes |
| PT65573A PT65573B (en) | 1975-09-11 | 1976-09-10 | NOVEL DERIVATIVES OF AMIDOXIMES PREPARATION THEREOF AND COMPOSITIONS CONTAINING SAME |
| IL50463A IL50463A (en) | 1975-09-11 | 1976-09-10 | Benzene-,furan-,thiophene-and pyrrole-carboxamidoxime derivatives,their preparation and phytohormonal and herbicidal compositions containing them |
| RO7687499A RO70581A (en) | 1975-09-11 | 1976-09-10 | PROCESS FOR THE PREPARATION OF AMIDOXYMES |
| BE170532A BE846081A (en) | 1975-09-11 | 1976-09-10 | NEW DERIVATIVES OF AMIDOXIMES, THEIR PREPARATION AND COMPOSITIONS CONTAINING |
| LU75766A LU75766A1 (en) | 1975-09-11 | 1976-09-10 | |
| PL1976192321A PL110263B1 (en) | 1975-09-11 | 1976-09-10 | Phytohormonal agent and a herbicide |
| AR264650A AR216448A1 (en) | 1975-09-11 | 1976-09-10 | NEW DERIVATIVES OF THIOFEN, FURAN, PIRROL OR PHENYL AMIDOXIMA CARBOXYLATE, PARTICULARLY USEFUL AS PHYTOHORMONAL AGENTS AND HERBICIDES, PROCEDURES FOR THE PREPARATION OF THESE NEW COMPOUNDS, AND PHYTOHORMONAL AND / OR HERBAL COMPOSITIONS THAT |
| CH1156076A CH603043A5 (en) | 1975-09-11 | 1976-09-10 | |
| DK410676A DK410676A (en) | 1975-09-11 | 1976-09-10 | AMIDOXINS WITH PHYTOHORMONAL AND / OR HERBICID EFFECT AND PROCEDURE FOR THE PRODUCTION OF SUCH AMIDOXINS |
| AT670076A AT355059B (en) | 1975-09-11 | 1976-09-10 | PHYTOHORMONAL AND HERBICIDAL COMPOSITIONS |
| JP51109352A JPS5236640A (en) | 1975-09-11 | 1976-09-10 | Production of novel amidoxime * composition containing same and treating method |
| SU762396746A SU862812A3 (en) | 1975-09-11 | 1976-09-10 | Phytohormonal composition |
| IT27129/76A IT1070587B (en) | 1975-09-11 | 1976-09-10 | DERIVATIVES OF AMOXIDE THEIR PREPARATION AND COMPOSITIONS CONTAINING THEM |
| SE7610050A SE7610050L (en) | 1975-09-11 | 1976-09-10 | AMIDOXIM DERIVATIVE |
| NL7610066A NL7610066A (en) | 1975-09-11 | 1976-09-10 | PROCESS FOR THE PREPARATION OF AMIDOXIM DERIBASES. |
| ES451407A ES451407A1 (en) | 1975-09-11 | 1976-09-10 | Herbicidal and phytohormonal amidoximes |
| US05/906,863 US4216006A (en) | 1975-09-11 | 1978-05-17 | Herbicidal and phytohormonal amidoximes |
| US05/928,371 US4188203A (en) | 1975-09-11 | 1978-07-27 | Herbicidal and phytohormonal amidoximes |
| SU792790407A SU886740A3 (en) | 1975-09-11 | 1979-07-26 | Method of preparing amidoxime derivatives |
| US06/116,452 US4324579A (en) | 1975-09-11 | 1980-01-29 | Herbicidal and phytohormonal amidoximes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7527884A FR2323683A1 (en) | 1975-09-11 | 1975-09-11 | Phytohormonal and herbicidal amidoxime derivs. - prepd. by treatment of an imino ether with an O-amino oxy-acetate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2323683A1 true FR2323683A1 (en) | 1977-04-08 |
| FR2323683B1 FR2323683B1 (en) | 1979-07-13 |
Family
ID=9159862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7527884A Granted FR2323683A1 (en) | 1975-09-11 | 1975-09-11 | Phytohormonal and herbicidal amidoxime derivs. - prepd. by treatment of an imino ether with an O-amino oxy-acetate |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR2323683A1 (en) |
| SU (2) | SU862812A3 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2103166B1 (en) * | 1992-08-26 | 1998-04-01 | Ciba Geigy Ag | PROCEDURE FOR OBTAINING BICYCLE AMIDINOHYDRAZONES. |
| ME02461B (en) | 2005-05-10 | 2017-02-20 | Incyte Holdings Corp | INDOLEAMINE 2,3-DIOXYGENASE MODULATORS AND METHODS FOR THE USE OF THE SAME |
| EP1971583B1 (en) | 2005-12-20 | 2015-03-25 | Incyte Corporation | N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase |
| CL2007002650A1 (en) | 2006-09-19 | 2008-02-08 | Incyte Corp | COMPOUNDS DERIVED FROM HETEROCICLO N-HIDROXIAMINO; PHARMACEUTICAL COMPOSITION, USEFUL TO TREAT CANCER, VIRAL INFECTIONS AND NEURODEGENERATIVE DISORDERS BETWEEN OTHERS. |
| US20080125470A1 (en) | 2006-09-19 | 2008-05-29 | Incyte Corporation | N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase |
| SG10201805844QA (en) | 2008-07-08 | 2018-08-30 | Incyte Holdings Corp | 1,2,5-oxadiazoles as inhibitors of indoleamine 2,3-dioxygenase |
| CA2929552C (en) | 2013-11-08 | 2022-05-17 | Incyte Holdings Corporation | Process for the synthesis of an indoleamine 2,3-dioxygenase inhibitor |
-
1975
- 1975-09-11 FR FR7527884A patent/FR2323683A1/en active Granted
-
1976
- 1976-09-10 SU SU762396746A patent/SU862812A3/en active
-
1979
- 1979-07-26 SU SU792790407A patent/SU886740A3/en active
Non-Patent Citations (1)
| Title |
|---|
| NEANT * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2323683B1 (en) | 1979-07-13 |
| SU886740A3 (en) | 1981-11-30 |
| SU862812A3 (en) | 1981-09-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |