CN105646348B - A kind of aphthalimide base α-naphthoacetyl isothiocyanate class compound and application thereof - Google Patents
A kind of aphthalimide base α-naphthoacetyl isothiocyanate class compound and application thereof Download PDFInfo
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- CN105646348B CN105646348B CN201610102618.8A CN201610102618A CN105646348B CN 105646348 B CN105646348 B CN 105646348B CN 201610102618 A CN201610102618 A CN 201610102618A CN 105646348 B CN105646348 B CN 105646348B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
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- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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Abstract
The invention discloses a kind of aphthalimide base naphthalene acetyl class thiourea compound of structure shown in formula I and its purposes as plant growth regulator.
Description
The invention belongs to plant growth regulator field in pesticide for technical field, and in particular to a kind of aphthalimide base
α-naphthoacetyl isothiocyanate class compound and its application.
Background technology
The basic element of cell division is a kind of important kind of plant growth regulator, is promoting crop cell division, increasing yield and improving quality
And enhancing crop anti-adversity etc. has played positive effect.Plant growth regulator main at present has：Gibberellin, DA-
6th, ethephon (CEPHA),2-(chloroethyl) phosphonic acid, methyl α-naphthyl acetate etc..These are all the conditioning agent species for having been used to commercialization, but new high-quality few in recent years
Noval chemical compound or for conditioning agent.Naphthalene diformylhydrazine (Formula II compound) has on agricultural production promotes plant life well
Long effect, in order to further improve its increasing yield and improving quality effect, and common plant growth regulator-methyl α-naphthyl acetate (formula III chemical combination
Thing) carry out group combination, enable to show both effects.Compound of formula I as described in the present invention and its apply
It is not disclosed both at home and abroad.
The content of the invention
The object of the present invention is to provide one kind to prepare easy, easy to use, efficient aphthalimide base naphthalene acetyl sulphur
Carbamide compounds, it is mainly used as the basic element of cell division, promotes crop yield.
Naphthalene acetyl isothiocyanates has an excellent cell division activity, and activity is better than comparison medicament naphthalene second under comparable sodium
Acid.The present invention on the basis of compound II by introducing thiourea group, there is provided the common increasing of naphthalene diformylhydrazine and methyl α-naphthyl acetate
Production acts on, and improves its application value, it can be used for the agriculturally volume increase of crop or survival rate to improve.
Technical scheme is as follows：
The present invention provides a kind of aphthalimide base acyl thiourea compound, structure is shown in formula I：
Compound of formula I can be made by following reaction：
Formula III compound generates compound IV (naphthalene acetyl with thionyl chloride in toluene under conditions of being heated to reflux
Chlorine), solvent toluene and excessive thionyl chloride are then rotated out, obtains yellow oil.Then in ethyl acetate solvent, add
Enter KSCN, stir lower dropwise addition naphthalene chloroacetic chloride, drop finishes.The reaction was continued 4h, adds naphthalene diformylhydrazine (less than 10 degree of control), room temperature is anti-
2h is answered, is filtered, removes KCl, washing, is drained, and is dried.
The advantages and positive effects of the present invention：
The basic element of cell division and Formula II, III compound phases ratio with commercialization, the aphthalimide base α-naphthoacetyl isothiocyanate class
Compound I has the cell division activity of higher, and its simple synthetic method, production cost are low；Compound I is existed by the present invention
Thiourea group is introduced on the basis of compound II, there is provided the common production-increasing function of naphthalene diformylhydrazine and methyl α-naphthyl acetate, improving it should
With value, it can be used for the agriculturally volume increase of crop or survival rate to improve.And have with other pesticides, fertilizer and cooperate with compatibility well
Performance.
The compounds of this invention and its salt as plant growth regulator in use, can be used alone, also can be with other work
Property material is applied in combination, to improve the comprehensive performance of product.
Plant growth regulator composition present invention additionally comprises compound of formula I and its as active component, said composition
Include compound of formula I as active component and agriculturally acceptable carrier.
The composition of the present invention can be used in the form of preparation：Compound of formula I and its salt be dissolved in as active component or
Be scattered in carrier or solvent, add suitable surfactant be made aqua, soluble concentrate, missible oil, microemulsion, aqueous emulsion,
Suspending agent etc..
It should be appreciated that in scope defined by the claims of the present invention, various conversion and change can be carried out.
Embodiment
Following synthesis example, formulation examples and raw test result can be used to further illustrate the present invention, but not mean that
The limitation present invention.
Synthesize example
The synthesis of example 1, aphthalimide base α-naphthoacetyl isothiocyanate class compound (Formulas I)
(1) naphthalene chloroacetic chloride is synthetically prepared
Take 20.8g (0.1mol) Nafusaku to be dissolved by heating with water, add hydrochloric acid and be adjusted to acidity, cooling separates out solid, dries
White methyl α-naphthyl acetate solid powder 18.2g, yield 97.8% are obtained after dry.
18.6g (0.1mol) compound III methyl α-naphthyl acetates are weighed, are added in 250mL three-necked flasks, using toluene as solvent, then
Add 14.3g (0.12mol) SOCl2, lower dropwise addition 0.2mL n,N-Dimethylformamide, temperature rising reflux 2h is stirred at room temperature.TLC is supervised
Survey reaction to complete, rotate out unnecessary toluene and thionyl chloride, obtain 19.6g claret oily naphthalene chloroacetic chlorides (formula IV compound) receipts
Rate is 95.6%.
(2) Formula II compound is synthetically prepared
19.8g (0.10ml) 1,8- naphthalic anhydrides and 50mL hydrazine hydrates are separately added into 250mL there-necked flasks, is flowed back
3h.Naturally room temperature is down to, filters, dries to obtain 20.6g crystal, yield 97.2%.
(3) compound of formula I is synthetically prepared
Take 10.7g (0.11mol) KSCN and 0.5gPEG 400 to be added in the three-necked flask of 250mL, be stirred at room temperature down,
20.5g (0.1mol) naphthalene chloroacetic chloride is slowly added dropwise, the reaction was continued 4h obtains product V.Add two formyl of 21.2g (0.1mol) naphthalene
Hydrazine (less than 10 degree of control), reacts at room temperature 2h, filters, remove KCl, filtrate plus water are rotated, white solid is obtained, claims after drying
Weight 38.2g, yield 87.0%.Fusing point：188.5 DEG C~190.8 DEG C.
Formulation examples
The preparation of example 2,10% compound of formula I suspending agent
10g compound of formula I, 2g sodium lignin sulfonates, 5 (Malaysias of 3g poly-hydroxy acid salt dispersant Sokalan CP are weighed respectively
Acid-acrylic acid sodium salt), 2.5g n-butanols, 3g ethylene glycol, 2g aluminium-magnesium silicates, 1g organosilicon breast defoamers in 250mL beakers,
76.5g water is added, is stirred evenly, grinds 2h with sand mill, rotating speed is 3000 revs/min, detects 3~4um of granularity, obtains white flowing
Property suspending agent.
It is raw to survey example
Example 3, wheat seed germinating experiment
Compound of formula I, Formula II compound, formula III compound are prepared into suspending agent by 2 method of example respectively, then with DA-
6 (Henan Zheng Shi Chemical Co., Ltd.s product) aquas and clear water compare.Be diluted with distilled water into respectively concentration for 10 μ g/mL,
The plant growth regulator solution of 20 μ g/mL, 40 μ g/mL and 80 μ g/mL.By wheat seed with above-mentioned dilution culture 8h, often
100 seeds are handled, seed, is placed in the culture dish of double-layer filter paper by 3 repetitions after processing every time, and 25 DEG C of insulations are urged
Bud, and keep filter paper to moisten, the germination of each processing is observed in vernalization, radicel length is standard about with the 1/2 of seed length, in
Wheat germination rate in each ware is counted after 24h, while is compared with the DA-6 of same concentrations and clear water (CK), while calculates each dilution
Liquid germination promotion rate, as a result such as table 1 below.
1 wheat seed germinating test data of table
As can be seen from Table 1, the germination percentage that compound of formula I of the invention is respectively handled is better than Formula II chemical combination on the whole
Thing, formula III compound, DA-6 comparison medicaments, are more significantly better than the situation of clear water processing (CK).
Embodiment 4, the root experiment of seed soaking growth-promoting
Compound of formula I, Formula II compound, 10% suspending agent of formula III compound and DA-6 aquas are used respectively respectively
It is molten for the plant growth regulator of 10 μ g/mL, 20 μ g/mL, 30 μ g/mL, 60 μ g/mL and 120 μ g/mL that distilled water is diluted to concentration
Liquid.The wheat seed that Seed size is uniform, full is selected, after being sterilized with hypochlorite solution to seed, puts it into gauze
In, 10h is soaked with above-mentioned dilution in beaker, then by wheat seed uniform discharge on the paper bed of moistening, embryo when putting bed
Portion will have a certain distance upward towards the same side between seed, and to ensure that seed fully absorbs moisture, each processing puts 20
Grain wheat, is well placed seed and puts it into progress germination treatment 24h in complete intelligent weather vegetation box afterwards, during which periodically to add
Distilled water makes paper bed keep moistening.Treat that wheat main root exposes 2mm or so, by its kind in the solid medium solidified, respectively
Processing is repeated 3 times, and is then placed in complete intelligent weather vegetation box and is cultivated.It is high with kind of calliper main root, stem after 40h, and
Make detailed record.Compared at the same time with the DA-6 of same concentrations and clear water (CK), as a result such as table 2 below.
The seed soaking Rooting data of table 2
The compounds of this invention reaches wheat seed soaking rush rooting efficiency in 60 μ g/mL concentration it can be seen from the result of table 2
To optimal.
Example 5, field experiment
3 processing are set altogether to apple experiment, the suitable bough of new upper 3 growth potentials of Gala apple tree of each processing selection into
OK, experiment takes strain at random, and tree-plot, 3 repetitions, respectively spray one in red fuji apple young fruit period and fruit expanding period respectively
Secondary, foliage-spray clear water and DA-6 after harvest, measure the index of quality of apple respectively as compareing, wherein, VC contents use 2,
6- dichloropheno-lindophenols method measures, and soluble sugar content is measured using anthrone colorimetry, as a result such as table 3 below.
3 apple quality test data of table
To sum up data, it can be seen that compound of formula I of the invention has remarkable result at germination, aspect of taking root, excellent
In contrast agents (DA-6), methyl α-naphthyl acetate and naphthalene diformylhydrazine；After carrying out foliage-spray to apple, while apple production is improved
Improve the appearance and interior quality of apple, it can be seen that compound of the invention is a kind of plant growth of excellent combination property
Conditioning agent.
Claims (4)
1. a kind of aphthalimide base α-naphthoacetyl isothiocyanate class compound of structure shown in formula I,
2. the purposes of aphthalimide base α-naphthoacetyl isothiocyanate class compound according to claim 1, it is characterised in that Formulas I
Compound is used as plant growth regulator.
3. plant growth of the aphthalimide base α-naphthoacetyl isothiocyanate class compound according to claim 1 as crops
The application method of conditioning agent：According to plant growth needs, using foliar spray, seed treatment, root processing, agent, soil treatment method
Implemented, concentration is 0.1~1000 μ g/mL effective dosies.
4. a kind of plant growth regulator composition, contains the compound of formula I described in claim 1 as plant growth regulator
Acceptable carrier in active component and agricultural or forestry.
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| CN201610102618.8A CN105646348B (en) | 2016-02-25 | 2016-02-25 | A kind of aphthalimide base α-naphthoacetyl isothiocyanate class compound and application thereof |
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| CN201610102618.8A CN105646348B (en) | 2016-02-25 | 2016-02-25 | A kind of aphthalimide base α-naphthoacetyl isothiocyanate class compound and application thereof |
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| CN105646348B true CN105646348B (en) | 2018-04-20 |
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| FR2970965A1 (en) * | 2011-01-31 | 2012-08-03 | Centre Nat Rech Scient | ANTI-ANGIOGENIC COMPOUNDS, PHARMACEUTICAL COMPOSITIONS COMPRISING SAME, AND USE THEREOF |
| US10596164B2 (en) * | 2014-04-15 | 2020-03-24 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Anti-clostridium compounds |
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Non-Patent Citations (2)
| Title |
|---|
| Preparation of some alkenoic acid derivatives as new plant growth regulators;Kayed A. Abu Safieh等;《Res Chem Intermed》;20130625;第41卷;1863-1872 * |
| 水果中常用植物生长调节剂的研究进展;史晓梅等;《食品工业科技》;20121231;第33卷(第4期);第417-422、426页 * |
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Inventor after: Wang Yang Inventor after: Wang Minghui Inventor after: Ju Guangxiu Inventor after: Xu Shanshan Inventor after: Chen Gexin Inventor after: Xu Liangzhong Inventor after: Niu Shuyan Inventor before: Wang Minghui Inventor before: Ju Guangxiu Inventor before: Xu Panpan Inventor before: Chen Gexin Inventor before: Xu Liangzhong Inventor before: Niu Shuyan |
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