DESC:FORM 2
THE PATENTS ACT, 1970
[39 of 1970]
&
THE PATENTS RULES, 2003
COMPLETE SPECIFICATION
(Section 10; Rule 13)
DESIGN AND SYNTHESIS OF A NEW SALICYLY-FORMAZONE OF POTENT BIOACTIVITY
PHYTOTRON AGRO PRODUCTS (INDIA) PVT. LTD.
Thirumenahalli, Yelahanka, Bangalore - 560064,
Karnataka, India
[An Indian Company]
The following Specification particularly describes the invention and the manner in which it is to be performed
FIELD OF INVENTION
[001] The present invention relates to design and synthesis of synthetic process of a potent Anti-Viral formazan. More specifically, it relates to a Schiff base conjugate of bioactive PAS and a Hydrazone, to form a formazan of formula (I) that has the chemical name 1- (3-hydroxy, 4-carboxylic) -3- (4-acetoxy -3-methoxy phenyl) -5- phenyl formazone.
BACKGROUND OF THE PRESENT INVENTION
[002] Wherefore, Salicylate molecules have been associated with the Induced Anti-Viral Resistance in plants, a synthetic process which could prepare 1- (3-hydroxy, 4-carboxylic) -3- (4-acetoxy -3-methoxy phenyl) -5- phenyl formazone of a well know anti-bacterial like PAS was achieved with high efficiently at a higher yield and in a form that has been shown to exhibit Anti-Viral potency.
SUMMARY OF THE PRESENT INVENTION
[003] The present invention provides a synthetic process for preparation of formazone of formula (I) that has the chemical name 1- (3-hydroxy, 4-carboxylic) -3- (4-acetoxy -3-methoxy phenyl) -5- phenyl formazone in an overall yield of 91%. The process includes coupling reaction of a 4-acetoxy-3-meythoxy benzaldehyde phenyl hydrazine compound (IV) with a Diazonium salt of 4-amino salicylic acid compound (V). The coupling reaction may be accomplished by mild basic
condition, preferably together with a tertiary amine (e.g. Pyridine) in an inert solvent (e.g. aqueous pyridine).The ratio of the 4-acetoxy-3-meythoxy benzaldehyde phenyl hydrazine compound (IV) with the Diazonium salt of 4-amino salicylic acid compound (V) in the aqueous pyridine is 2:8. Further stirring the mixture of the 4 acetoxy-3-meythoxy benzaldehyde phenyl hydrazine compound (IV), the Diazonium salt of 4-amino salicylic acid compound (V) and the aqueous pyridine with in temperature range of -10°c to 50°c thereby yielding the 1-(3-hydroxy-4-carboxylic)-3-(4-acetoxy-3-methoxy-phenyl)-5- phenyl formazone of formula (I) . The coupling reaction is performed at near room temperature.
[004] In another embodiment of the present invention, the end product of the aforementioned process is a novel salicyly-formazone having chemical formula 1- (3-hydroxy, 4-carboxylic) -3- (4-acetoxy -3-methoxy phenyl) -5- phenyl formazone.
[005] The new hybrid molecule has shown potential bioactivity, as tested against Yellow Mosaic Virus Disease of Soybean.
OBJECTIVES OF THE PRESENT INVENTION
[006] The main objective of the present invention is to design a conjugate of two known bio-active molecules, in the form of a well-defined compound of the type of a formazan, formula (I) and establishing the bio-efficacy of the final product as Anti-Viral.
[007] Another objective of the present invention by conjugating known bio-active Hydrazone and amino salicylic acid [3-4] thus yielding the hybrid molecule of formula (I) that has a potential to exhibit a higher biological potency.
DETAILED DESCRIPTION OF THE PRESENT INVENTION
[008] The present invention provides for a process for the preparation of 1-(3-hydroxy-4-carboxylic)-3-(4- acetoxy – 3 - methoxy phenyl) – 5 - phenyl formazone of formula (I) from 4-acetoxy -3- methoxy benzaldehyde - phenylhydrazone of formula (IV), a facilitator for synthesizing the desired conjugate of p-amino-salicylic acid in the synthetic process, thus yielding the desired novel formazan.
[009] In the following detailed description of the embodiments of the invention, the embodiments are described in sufficient detail to enable those skilled in the art to practice the invention, and it
is to be understood that other embodiments may be utilized and that changes may be made without departing from the scope of the present invention. The following detailed description is, therefore, not to be taken in a limiting sense, and the scope of the present invention is defined only by the appended claims.
[010] The specification may refer to “an”, “one” or “some” embodiment(s) in several locations. This does not necessarily imply that each such reference is to the same embodiment(s), or that the feature only applies to a single embodiment. Single features of different embodiments may also be combined to provide other embodiments.
[011] As used herein, the singular forms “a”, “an” and “the” are intended to include the plural forms as well, unless expressly stated otherwise. It will be further understood that the terms “includes”, “comprises”, “including” and/or “comprising” when used in this specification, specify the presence of stated features, and steps, but do not preclude the presence or addition of one or more other features and steps and/or groups thereof. As used herein, the term “and/or” includes any and all combinations and arrangements of one or more of the associated listed items.
[012] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.
[013] The present embodiments have been described with reference to specific example embodiments; it will be evident that various modifications and changes may be made to these embodiments without departing from the broader spirit and scope of the various embodiments.
[014] Although the embodiments herein are described with various specific embodiments, it will be obvious for a person skilled in the art to practice the invention with modifications. However, all such modifications are deemed to be within the scope of the claims. It is also to be understood that the following claims are intended to cover all of the generic and specific features of the embodiments described herein and all the statements of the scope of the embodiments which as a matter of language might be said to fall there between.
[015] In one embodiment of the present invention, a synthetic process for synthesis of compound of formazan formula (I).
[016] The process includes coupling reaction of 4-acetoxy-3-methoxy benzaldehyde phenyl hydrazone compound (IV) with diazonium salt of 4-amino salicylic acid compound (V) in aqueous pyridine (2:8). The said mixture being stirred while maintaining the temperature at -10°C to 50°C, preferably near room temperature. Workup and crystallization yields the desired formazan of formula (I) as brown solid. The yield of the present process is considerably high about 91%.
[017] The novel hybrid molecule of formula (I) so prepared by conjugating the bio-active hydrazone and amino salicylic acid has a potential to exhibit a higher biological potency.
[018] In one embodiment of the present invention, a synthetic process for preparation of 1-(3-hydroxy-4-carboxylic)-3-(4-acetoxy-3-methoxy-phenyl)-5- phenyl formazone of formula (I), wherein the process comprising:
reacting 4-acetoxy-3-meythoxy benzaldehyde phenyl hydrazine compound (IV) with Diazonium salt of 4-amino salicylic acid compound (V) in aqueous pyridine, wherein ratio of the 4-acetoxy-3-meythoxy benzaldehyde phenyl hydrazine compound (IV) with Diazonium salt of 4-amino salicylic acid compound (V) in aqueous pyridine is 8:2.
stirring the mixture of 4 acetoxy-3-meythoxy benzaldehyde phenyl hydrazine compound (IV), Diazonium salt of 4-amino salicylic acid compound (V) and aqueous pyridine with in temperature range of -10°c to 50°c to prepare 1-(3-hydroxy-4-carboxylic)-3-(4-acetoxy-3-methoxy-phenyl)-5- phenyl formazone of formula (I) .
[019] In one embodiment of the present invention, A compound: 1-(3-hydroxy-4-carboxylic)-3-(4-acetoxy-3-methoxy-phenyl)-5- phenyl formazone of formula (I):
wherein a hydrazone and amino salicylic acid reacted with each other to produce the 1-(3-hydroxy-4-carboxylic)-3-(4-acetoxy-3-methoxy-phenyl)-5- phenyl formazone formula (I). The compound 1-(3-hydroxy-4-carboxylic)-3-(4-acetoxy-3-methoxy-phenyl)-5- phenyl formazone formula (I) is conjugate of 4-acetoxy-3-meythoxy benzaldehyde phenyl hydrazine compound (IV) and Diazonium salt of 4-amino salicylic acid compound (V).
[020] The hybrid molecule of formula (I) has been found effective as an Anti-Viral compound, as in cases of Yellow Mosaic Virus Disease of Soybeans, a disease which at times can cause up to 80% crop-loss in Soybean, an important source of Protein, edible Oil and Animal feed.
Hydrazone of compound formula (IV)
[021] 1H NMR (400 MHz, DMSO) = d 2.26 (3H, s, OAc CH3), 3.83 (3H, s, CH3), 3.97 (1H, NH), 6.73-7.39 (8H, m, Ar), 8.04 (1H, CH): 13C NMR (CDCl3): 26.6, 55.8, 113.2, 113.9, 121.4, 122.4, 129.5, 129.8, 129.9, 142.7, 143.0, 143.3, 160.1, 198
IR (KBr Pellet, cm-1): 3310.2, 1744.3, 1603.5, 1577.5, 1221.7, 1194.7.
Formazan of compound formula (I)
[022] 1H NMR (400 MHz, DMSO) = d 2.29 (3H, s, OAc CH3), 3.83 (3H, s, OCH3), 4.02 (1H, NH), 7.06-8.12 (11H, m, Ar), 12.95 (1H, COOH): 13C NMR (CDCl3): 26.6, 55.8, 113.2, 113.9, 116.3, 118.2, 121.3, 121.4, 122.4, 129.5, 129.8, 129.9, 131.7, 135.3, 140.1, 143.0, 155.0, 160.1, 162.2, 171.8, 198.0
IR (KBr Pellet, cm-1): 2957.3, 2927.4, 2872.5, 2853.2, 1729.8, 1657.5, 1619.9, 1456.0, 1284.4, 1256.4, 1142.6, 1118.5.
EXAMPLE
[023] The present invention is explained further in the following specific example which are only by way of illustration and are not to be construed as limiting the scope of the invention.
Example 1: preparation of 1-(3-hydroxy-4-carboxylic)-3-(4- acetoxy -3- methoxy phenyl) -5- phenyl formazone of formula (I)
Biological Evaluation
[024] Bio-efficacy of the thus prepared and formulated Formazan was conducted under the auspices of ICAR-All India Coordinated Research Program on Soybean, in different agro-ecological zones of India and within the Viral-hots-pots identified by ICARP-ICAR, during Year 2017-2018 & 2018-2019.
[025] The Data on Disease prevalence and the various treatments applied at 15th, 30th, and 45th day from planting as tried at doses of 4 ml / Lit and 6 ml / Lit. of 0.5% active compound were carried out. The application of the Bio-active compound (1) in the form of a spray solution, on crop-foliage and tender branches, well demonstrated the usefulness of the new innovation in with-holding the viral infestation levels with the Soybean crop and thus improving the crop-viability and crop Yields. ,CLAIMS:I/ We Claim:
1. A synthetic process for preparation of a 1-(3-hydroxy-4-carboxylic)-3-(4-acetoxy-3-methoxy-phenyl)-5- phenyl formazone of formula (I), wherein the process comprising:
reacting a 4-acetoxy-3-meythoxy benzaldehyde phenyl hydrazine compound (IV) with a Diazonium salt of 4-amino salicylic acid compound (V) in an aqueous pyridine,
wherein ratio of the 4-acetoxy-3-meythoxy benzaldehyde phenyl hydrazine compound (IV) with the Diazonium salt of 4-amino salicylic acid compound (V) in the aqueous pyridine is 2:8
stirring the mixture of the 4 acetoxy-3-meythoxy benzaldehyde phenyl hydrazine compound (IV), the Diazonium salt of 4-amino salicylic acid compound (V) and the aqueous pyridine with in temperature range of -10°c to 50°c thereby yielding the 1-(3-hydroxy-4-carboxylic)-3-(4-acetoxy-3-methoxy-phenyl)-5- phenyl formazone of formula (I) .

2. The synthetic process as claimed in claim 1, wherein the yield of the 1-(3-hydroxy-4-carboxylic)-3-(4-acetoxy-3-methoxy-phenyl)-5- phenyl formazone of formula (I) through the present process is 91%.
3. The synthetic process as claimed in claim 1, wherein the 1-(3-hydroxy-4-carboxylic)-3-(4-acetoxy-3-methoxy-phenyl)-5- phenyl formazone of formula (I) is an effective anti-viral compound.

4. A compound: 1-(3-hydroxy-4-carboxylic)-3-(4-acetoxy-3-methoxy-phenyl)-5- phenyl formazone of formula (I):

5. The compound as claimed in claim 4, wherein a hydrazone and an amino salicylic acid reacted with each other in an aqueous pyridine to produce the 1-(3-hydroxy-4-carboxylic)-3-(4-acetoxy-3-methoxy-phenyl)-5- phenyl formazone formula (I).
6. The compound as claimed in claim 4, wherein the hydrazone is a 4-acetoxy-3-meythoxy benzaldehyde phenyl hydrazine compound (IV).
7. The compound as claimed in claim 4, wherein the amino salicylic acid is a Diazonium salt of 4-amino salicylic acid compound (V).
8. The compound as claimed in claim 4, wherein the ratio of the 4-acetoxy-3-meythoxy benzaldehyde phenyl hydrazine compound (IV) and the Diazonium salt of 4-amino salicylic acid compound (V) in the aqueous pyridine is 2:8.

Dated this 6th Day of August 2019
Signature

Birendra Kumar
IN PA: 1102
Agent For the Applicant