CN111109261A - Application of a kind of 3-hydroxy-3-methylglutamic acid in the preparation of pesticides - Google Patents
Application of a kind of 3-hydroxy-3-methylglutamic acid in the preparation of pesticides Download PDFInfo
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- CN111109261A CN111109261A CN201911300258.2A CN201911300258A CN111109261A CN 111109261 A CN111109261 A CN 111109261A CN 201911300258 A CN201911300258 A CN 201911300258A CN 111109261 A CN111109261 A CN 111109261A
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- glutamic acid
- pesticides
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- HZFTUXIGLROGFG-NJXYFUOMSA-N (2s)-2-amino-3-hydroxy-3-methylpentanedioic acid Chemical compound OC(=O)CC(O)(C)[C@H](N)C(O)=O HZFTUXIGLROGFG-NJXYFUOMSA-N 0.000 title claims abstract description 43
- 239000000575 pesticide Substances 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims description 17
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 20
- 239000002917 insecticide Substances 0.000 claims abstract description 14
- 241000255967 Helicoverpa zea Species 0.000 claims abstract description 10
- 241000255908 Manduca sexta Species 0.000 claims abstract description 10
- 241000256247 Spodoptera exigua Species 0.000 claims abstract description 10
- 241000985245 Spodoptera litura Species 0.000 claims abstract description 10
- 241001674044 Blattodea Species 0.000 claims abstract description 8
- 241000500437 Plutella xylostella Species 0.000 claims abstract description 8
- 230000000694 effects Effects 0.000 abstract description 9
- 241000500441 Plutellidae Species 0.000 abstract description 2
- 230000002265 prevention Effects 0.000 abstract 1
- NPOAOTPXWNWTSH-UHFFFAOYSA-N 3-hydroxy-3-methylglutaric acid Chemical compound OC(=O)CC(O)(C)CC(O)=O NPOAOTPXWNWTSH-UHFFFAOYSA-N 0.000 description 14
- 229930014550 juvenile hormone Natural products 0.000 description 14
- 239000002949 juvenile hormone Substances 0.000 description 14
- 150000003633 juvenile hormone derivatives Chemical class 0.000 description 14
- 241000238631 Hexapoda Species 0.000 description 9
- 230000001276 controlling effect Effects 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000001988 toxicity Effects 0.000 description 6
- 231100000419 toxicity Toxicity 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 210000002784 stomach Anatomy 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 4
- 239000005898 Fenoxycarb Substances 0.000 description 3
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000653072 Euthyrrhapha pacifica Species 0.000 description 2
- 206010033799 Paralysis Diseases 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 210000005036 nerve Anatomy 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- LFXSHFHOJMKZDE-UHFFFAOYSA-N 2-formamidobenzamide Chemical compound NC(=O)C1=CC=CC=C1NC=O LFXSHFHOJMKZDE-UHFFFAOYSA-N 0.000 description 1
- MICKYFKVFXSLJI-UHFFFAOYSA-N 2-hydroxy-3-methylpentanedioic acid Chemical compound OC(=O)CC(C)C(O)C(O)=O MICKYFKVFXSLJI-UHFFFAOYSA-N 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 102000004286 Hydroxymethylglutaryl CoA Reductases Human genes 0.000 description 1
- 108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 description 1
- 102000007330 LDL Lipoproteins Human genes 0.000 description 1
- 108010007622 LDL Lipoproteins Proteins 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 description 1
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 description 1
- 241000238675 Periplaneta americana Species 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 229930191400 juvenile hormones Natural products 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 230000029052 metamorphosis Effects 0.000 description 1
- 238000001531 micro-dissection Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 239000000447 pesticide residue Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000019617 pupation Effects 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000033458 reproduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 102000042094 ryanodine receptor (TC 1.A.3.1) family Human genes 0.000 description 1
- 108091052345 ryanodine receptor (TC 1.A.3.1) family Proteins 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000002948 striated muscle cell Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
Classifications
-
- 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
- A01N37/36—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
-
- 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
- A01N37/44—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
Landscapes
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention relates to an application of 3-hydroxy-3-methyl glutamic acid in preparing insecticide, wherein the structural formula of the 3-hydroxy-3-methyl glutamic acid is shown as follows:
Description
Technical Field
The invention belongs to the technical field of pesticides, and relates to application of 3-hydroxy-3-methyl glutamic acid in preparation of an insecticide.
Background
As an important component of the comprehensive treatment of pests, the pesticide makes outstanding contribution to the health of people and the stable and high yield of agriculture. With the widespread use of pesticides, a series of problems such as drug resistance, environmental pollution, non-target biotoxicity, pesticide residue and accumulation also ensue. Therefore, new ideas, methods and technologies are needed to find new pesticide varieties with novel structures, unique action mechanisms and eco-friendly environment.
Juvenile Hormone (JH) is an important Hormone secreted by the insect pharyngeal sideroplasma, and its main functions include keeping the characteristics of larvae, maintaining the prothymus gland and promoting the maturation of ovaries, and regulating the development, metamorphosis and reproduction processes of insects. JH has been a hotspot in entomology and agro-pharmacology research. In recent years, many scientists have focused on the creation of inhibitors of JH biosynthesis.
In medicine, 3-hydroxy-3-methylglutaric acid (meglutong) is an anti-lipid agent, lowers cholesterol, triglycerides and serum β -lipoproteins and phospholipids, and inhibits hydroxymethylglutaryl-coa reductase activity, but its use in pesticides has not been reported.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide an application of 3-hydroxy-3-methyl glutamic acid in preparing pesticides.
The purpose of the invention can be realized by the following technical scheme:
the application of 3-hydroxy-3-methyl glutamic acid in preparing pesticide is disclosed, the structural formula of the 3-hydroxy-3-methyl glutamic acid is shown as follows:
further, the 3-hydroxy-3-methyl glutamic acid is used for preparing pesticides and application in agricultural and sanitary pest control.
Furthermore, the 3-hydroxy-3-methyl glutamic acid is used for preparing the insecticide for preventing and controlling the cotton bollworm.
Furthermore, the 3-hydroxy-3-methyl glutamic acid is used for preparing a pesticide for preventing and controlling diamondback moth.
Further, the 3-hydroxy-3-methyl glutamic acid is used for preparing a pesticide for preventing and controlling tobacco hornworm.
Furthermore, the 3-hydroxy-3-methyl glutamic acid is used for preparing an insecticide for preventing and controlling beet armyworm.
Further, the 3-hydroxy-3-methyl glutamic acid is used for preparing a pesticide for preventing and controlling prodenia litura.
Further, the 3-hydroxy-3-methyl glutamic acid is used for preparing an insecticide for preventing and controlling cockroaches.
Most of the existing pesticides belong to nerve toxicants. For example, neonicotinoid insecticides, which are currently in widespread use, act on the central nervous system of insects as agonists at the postsynaptic nicotinic acetylcholine receptors (nachrs). Pyrethroid insecticides kill insects by disturbing the normal physiology of the insect nerve from excitation, spasm to paralysis. The o-formylaminobenzamide insecticide mainly activates a ryanodine receptor, releases calcium ions stored in smooth muscle cells and striated muscle cells, and causes weak muscle regulation and paralysis until pests die finally. The structure of the 3-hydroxy-3-methyl glutamic acid is different from that of the commercial pesticide, and the compound does not act on the nervous system of pests, but plays a role in preventing and controlling the pests by inhibiting the synthesis of juvenile hormone of the pests, is completely different from the insecticidal mechanism of the existing commercial pesticide, and has great application potential in the aspect of controlling resistant pests.
Compared with the prior art, the invention has the following characteristics:
1) the invention widens the application field of the 3-hydroxy-3-methyl glutamic acid, and applies the 3-hydroxy-3-methyl glutamic acid to the pesticide for the first time;
2) the compound provided by the invention can control various agricultural and sanitary pests, and has an obvious effect on cotton bollworms, diamond back moths, tobacco hornworms, beet armyworms, prodenia lituras and cockroaches.
Detailed Description
The present invention will be described in detail with reference to specific examples. The present embodiment is implemented on the premise of the technical solution of the present invention, and a detailed implementation manner and a specific operation process are given, but the scope of the present invention is not limited to the following embodiments.
The 3-hydroxy-3-methylglutaric acid in the following examples is available from MedChemexpress; the insects are purchased from biological pesticide Limited company of Keyun, Henan province, and then are bred in a laboratory;
the raising conditions of the test insects are as follows: the feed is purchased from biological pesticide Limited company of Keyun, Henan province, with tap water as water source, feeding temperature of 28 + -1 deg.C, relative humidity of 50-70%, and photoperiod of L14: D10.
Example 1:
3-hydroxy-3-methyl glutamic acid for the pest juvenile hormone biosynthesis inhibitory activity.
1. The test method comprises the following steps:
in the present example, the juvenile hormone GC-MS/MS assay method (Journal of Chromatography a,2018,1538:67-74) is used to determine the inhibitory effect of compound 3-hydroxy-3-methylglutaric acid on the biosynthesis of juvenile hormones of cotton bollworm, diamond back moth, tobacco hornworm, beet armyworm, prodenia litura and pacific cockroaches, and the specific operations are as follows:
after anesthetizing the test insects with ice, they were placed on wax trays, the pharyngeal sideroplasms (CA) were removed by microdissection, and the surrounding connective tissue was removed in M199 for bioassay. Respectively placing CA in 100 μ L M199 containing 20nM internal standard substance citronellol and different concentrations of inhibitor (3-hydroxy-3-methyl glutamic acid), culturing at room temperature under slight shaking and dark for 3 hr; then 200 mu L of n-hexane is used for extraction, 150 mu L of upper organic phase is taken, and the JH content is determined by GC-MS/MS. The concentrations of the prepared inhibitors are 0.001 mu M, 0.01 mu M, 0.1 mu M, 1 mu M, 10 mu M and 100 mu M respectively, the JH content corresponding to the inhibitors with different concentrations is determined according to the method, and an inhibition curve is drawn by GraphPad 5.0, so that the concentration in inhibition is obtained. The experimental procedure of the control experiment was identical to that described above, except that no inhibitor was added.
2. Analysis and discussion of results:
the compound 3-hydroxy-3-methyl glutamic acid is used for killing bollworm, diamondback moth,IC for biosynthesis of juvenile hormone from tobacco hornworm, beet armyworm, prodenia litura and Pacific leafflower cockroach50The values are shown in Table 1.
TABLE 13 inhibitory Activity of hydroxy-3-methylglutaric acid on biosynthesis of juvenile hormone of pests (IC)50Unit μ M)
| Bollworm | Diamondback moth | Tobacco hornworm | Beet armyworm | Prodenia litura | Pacific folding wing cockroach |
| 1.62 | 0.55 | 2.07 | 3.74 | 7.64 | 23.81 |
As can be seen from the results in Table 1, 3-hydroxy-3-methylglutaric acid is effective in inhibiting juvenile hormone biosynthesis of cotton bollworm, diamond back moth, tobacco hornworm, beet armyworm, prodenia litura and Pacific cockroach.
Example 2:
and (3) measuring the stomach toxicity activity of the 3-hydroxy-3-methyl glutamic acid to pests.
1. The test method comprises the following steps:
(1) stomach toxicity activity of lepidoptera pest (Cotton bollworm, diamondback moth, tobacco hornworm, beet armyworm and prodenia litura)
The larvae of the lepidopteran pests which have just hatched are placed on the feed added with the 3-hydroxy-3-methyl glutamic acid with different concentrations. The feed was changed once a day. The control group was supplemented with the corresponding weight of solvent (pure water) and the remaining conditions were identical to the experimental groups, each containing 10 replicates, with 10 larvae per experiment. From the application, dead worm numbers were recorded daily until the larvae stopped feeding into pupation, and mortality was finally recorded.
(2) Stomach toxicity activity of Blattales pest (Pacific folded cockroaches, Periplaneta americana and German cockroach)
20 cockroaches are placed into a square glass jar of 20cm multiplied by 20cm, unhealthy individuals are removed after normal rearing for 24h, and after corresponding supplementation, feed added with 3-hydroxy-3-methyl glutamic acid with different concentrations is placed, water is supplied normally, and the number of dead insects before the adult is developed is recorded. Control experiments the mortality of the worms was calculated using conventional feeding conditions, setting 5 replicates per concentration.
2. Analysis and discussion of results:
the results of the stomach-toxic activity of 3-hydroxy-3-methylglutaric acid against pests are shown in table 2.
TABLE 2 Compound 3-hydroxy-3-methylglutaric acid stomach toxicity Activity (mortality) against pests
From the test for determining the stomach toxicity activity, it can be seen that: the 3-hydroxy-3-methyl glutamic acid has practical application value for preventing and controlling pests, and provides a new choice for the development of pesticides. Under the same experimental conditions, toxicity of the commercial juvenile hormone analogue fenoxycarb against the above 8 pests was determined. At the two concentrations, the insecticidal effect of the 3-hydroxy-3-methyl glutamic acid and the fenoxycarb is equivalent. Compared with the fenoxycarb, the 3-hydroxy-3-methylglutaric acid has simpler structure, simpler synthetic process, lower cost and higher market competitiveness.
The embodiments described above are described to facilitate an understanding and use of the invention by those skilled in the art. It will be readily apparent to those skilled in the art that various modifications to these embodiments may be made, and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above embodiments, and those skilled in the art should make improvements and modifications within the scope of the present invention based on the disclosure of the present invention.
Claims (8)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911300258.2A CN111109261A (en) | 2019-12-16 | 2019-12-16 | Application of a kind of 3-hydroxy-3-methylglutamic acid in the preparation of pesticides |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911300258.2A CN111109261A (en) | 2019-12-16 | 2019-12-16 | Application of a kind of 3-hydroxy-3-methylglutamic acid in the preparation of pesticides |
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| CN111109261A true CN111109261A (en) | 2020-05-08 |
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| CN201911300258.2A Pending CN111109261A (en) | 2019-12-16 | 2019-12-16 | Application of a kind of 3-hydroxy-3-methylglutamic acid in the preparation of pesticides |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113767913A (en) * | 2021-08-13 | 2021-12-10 | 上海应用技术大学 | Application of a kind of 2-[(4-chloro-3-nitrophenyl) sulfonamido] benzoic acid in preparing insect growth regulator |
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| GB955685A (en) * | 1960-03-04 | 1964-04-15 | Jeremiah Forster Twomey | Enzyme forming plant stimulating composition |
| US3707491A (en) * | 1969-04-09 | 1972-12-26 | Ceskoslovenska Akademie Ved | Insecticide with juvenile hormone activity and a process of its preparation |
| US4208204A (en) * | 1977-10-07 | 1980-06-17 | Calbiochem-Behring Corp. | 3-Hydroxy-3-methylglutaric acid monoamide and derivatives thereof |
| JPH07308136A (en) * | 1994-05-17 | 1995-11-28 | Daiichi Seimo Kk | Agent for controlling disease injury of cultured laver |
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2019
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113767913A (en) * | 2021-08-13 | 2021-12-10 | 上海应用技术大学 | Application of a kind of 2-[(4-chloro-3-nitrophenyl) sulfonamido] benzoic acid in preparing insect growth regulator |
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