PL430867A1 - Imine derivatives of salicylic aldehydes and acid hydrazides, their preparation method and their application - Google Patents

Imine derivatives of salicylic aldehydes and acid hydrazides, their preparation method and their application

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Publication number
PL430867A1
PL430867A1 PL430867A PL43086719A PL430867A1 PL 430867 A1 PL430867 A1 PL 430867A1 PL 430867 A PL430867 A PL 430867A PL 43086719 A PL43086719 A PL 43086719A PL 430867 A1 PL430867 A1 PL 430867A1
Authority
PL
Poland
Prior art keywords
hoc6h4
ch3oc6h4
formula
salicylaldehydes
acid hydrazides
Prior art date
Application number
PL430867A
Other languages
Polish (pl)
Other versions
PL241843B1 (en
Inventor
Mirosław Giurg
Halina Maniak
Original Assignee
Politechnika Wrocławska
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 Politechnika Wrocławska filed Critical Politechnika Wrocławska
Priority to PL430867A priority Critical patent/PL241843B1/en
Publication of PL430867A1 publication Critical patent/PL430867A1/en
Publication of PL241843B1 publication Critical patent/PL241843B1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • A01N37/18—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 containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/28—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 containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/16—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of hydrazones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones
    • C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Environmental Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)

Abstract

Przedmiotem wynalazku są iminowe pochodne aldehydów salicylowych i hydrazydów kwasowych o wzorze 6 lub o wzorze ogólnym 1, w którym R1 oznacza H, t-Bu, Ph, R2 oznacza H, CH3, t-Bu, R3 oznacza H, OCH3, R4 oznacza Ph, 2-HOC6H4, 3-HOC6H4, 4-HOC6H4, 3-CH3OC6H4, 4-CH3OC6H4, 3,5-(HO)2C6H3, 3-pirydyl, 2-(1-HO-naftyl) a n stanowi liczbę 0 lub 1. Wynalazek dotyczy również sposobu wytwarzania iminowych pochodnych aldehydów salicylowych i hydrazydów kwasowych przedstawionych wzorem 6 lub wzorem ogólnym 1, w którym R1 oznacza H, t-Bu, Ph, R2 oznacza H, CH3, t-Bu, R3 oznacza H, OCH3, R4 oznacza Ph, 2-HOC6H4, 3-HOC6H4, 4-HOC6H4, 3-CH3OC6H4, 4-CH3OC6H4, 3,5-(HO)2C6H3, 3-pirydyl, 2-(1-HO-nafty1) a n stanowi liczbę 0 lub 1, polegający na tym, że równomolową mieszaninę aldehydu salicylowego o wzorze 4 lub aldehydów salicylowych o wzorze ogólnym 2, w którym R1 oznacza H, t-Bu, Ph, R2 oznacza H, CH3, t-Bu, R3 oznacza H, OCH3, oraz hydrazydu kwasu octowego 5 lub hydrazydów kwasowych o wzorze ogólnym 3, w których R4 oznacza Ph, 2-HOC6H4, 3-HOC6H4, 4-HOC6H4, 3-CH3OC6H4, 4-CH3OC6H4, 3,5-(HO)2C6H3, 3-pirydyl, 2-(1-HO-naftyl) a n stanowi liczbę 0 lub 1 w rozpuszczalniku traktuje się kwasem octowym i reakcję prowadzi się we wrzącym rozpuszczalniku w temperaturze 338 K do praktycznego przereagowania substratów a następnie z mieszaniny poreakcyjnej wydziela się produkty. Przedmiot wynalazku ujawnia zastosowanie hydrazydo-hydrazonów pochodnych hydrazydów kwasowych i aldehydów salicylowych jako środków ochrony roślin, zwłaszcza środków przeciwgrzybicznych.The subject of the invention is imine derivatives of salicylaldehydes and acid hydrazides of formula 6 or formula 1, in which R1 is H, t-Bu, Ph, R2 is H, CH3, t-Bu, R3 is H, OCH3, R4 is Ph , 2-HOC6H4, 3-HOC6H4, 4-HOC6H4, 3-CH3OC6H4, 4-CH3OC6H4, 3,5- (HO) 2C6H3, 3-pyridyl, 2- (1-HO-naphthyl) and n is 0 or 1. The invention also relates to a process for the preparation of imine derivatives of salicylaldehydes and acid hydrazides represented by the formula 6 or the general formula 1, wherein R1 is H, t-Bu, Ph, R2 is H, CH3, t-Bu, R3 is H, OCH3, R4 is Ph, 2-HOC6H4, 3-HOC6H4, 4-HOC6H4, 3-CH3OC6H4, 4-CH3OC6H4, 3,5- (HO) 2C6H3, 3-pyridyl, 2- (1-HO-naphth1) an is 0 or 1 wherein an equimolar mixture of salicylaldehyde of formula 4 or salicylaldehydes of general formula 2, wherein R1 is H, t-Bu, Ph, R2 is H, CH3, t-Bu, R3 is H, OCH3, and acetic acid hydrazide 5 or acid hydrazides of general formula 3, k of which R4 is Ph, 2-HOC6H4, 3-HOC6H4, 4-HOC6H4, 3-CH3OC6H4, 4-CH3OC6H4, 3,5- (HO) 2C6H3, 3-pyridyl, 2- (1-HO-naphthyl) and the number 0 or 1 in the solvent is mixed with acetic acid and the reaction is carried out in the boiling solvent at 338 K until the reactants are practically converted, and then the products are separated from the reaction mixture. The subject of the invention relates to the use of hydrazide-hydrazones, derivatives of acidic hydrazides and salicylaldehydes, as plant protection agents, especially as antifungal agents.

PL430867A 2019-08-13 2019-08-13 Imine derivatives of salicylic aldehydes and acid hydrazides, their preparation method and their application PL241843B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PL430867A PL241843B1 (en) 2019-08-13 2019-08-13 Imine derivatives of salicylic aldehydes and acid hydrazides, their preparation method and their application

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PL430867A PL241843B1 (en) 2019-08-13 2019-08-13 Imine derivatives of salicylic aldehydes and acid hydrazides, their preparation method and their application

Publications (2)

Publication Number Publication Date
PL430867A1 true PL430867A1 (en) 2021-02-22
PL241843B1 PL241843B1 (en) 2022-12-12

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN118164872A (en) * 2024-03-12 2024-06-11 贵州大学 Eugenol compound containing Schiff base core skeleton, and preparation method and application thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN118164872A (en) * 2024-03-12 2024-06-11 贵州大学 Eugenol compound containing Schiff base core skeleton, and preparation method and application thereof

Also Published As

Publication number Publication date
PL241843B1 (en) 2022-12-12

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