CN108605932A - Application of two kinds of compounds in preparing nematicidal drug - Google Patents
Application of two kinds of compounds in preparing nematicidal drug Download PDFInfo
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- CN108605932A CN108605932A CN201810359220.1A CN201810359220A CN108605932A CN 108605932 A CN108605932 A CN 108605932A CN 201810359220 A CN201810359220 A CN 201810359220A CN 108605932 A CN108605932 A CN 108605932A
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- drug
- nematicidal
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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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
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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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/075—Ethers or acetals
- A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
- A61K31/09—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon having two or more such linkages
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
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- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Epidemiology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention relates to pesticide and pharmaceutical technology field, more particularly to application of the two kinds of compounds in preparing nematicidal drug.Two kinds of compounds of the invention are safe and reliable, it effectively agriculturally can prevent nematodiasis, medical to drive away nematosis worm, and have no toxic and side effect to human body and pharmacological dependence type, better than existing pesticide and medicine, can be widely applied in nematicide medicine preparation.
Description
Technical field
The present invention relates to pesticide and pharmaceutical technology field, more particularly to two kinds of compounds answering in preparing nematicidal drug
With.
Background technology
Nematode refers to the general designation for belonging to Nemathelminthes, and record type is various, and the whole world is seen everywhere, and wherein many kinds are to post
Natural disposition, up to 25 kinds of the parasitic nematode type that wherein China records, popular such as roundworm, pinworm and hookworm.With
The improvement such as medical and health conditions, monitoring pathogenic Soil transmitted helminths infection rate in the China 2005-2013 is reduced to from 20.88%
3.12%, but still largely endanger the health of the people.And agricultural and forestry eelworm harm are also very big, cause the agriculture underproduction
Total crop failure (such as root-knot nematode, estimation cause global crop loss to reach 100,000,000 dollars), large area tree death (such as pine tree black line
Worm) etc., threaten the grain and ecological safety in China.
Research drug endangers nematode to resist parasitic nematode and agricultural, has been a concern, and with agricultural well
With medical applications potentiality.Existing agricultural nematicidal mainly has the organophosphorus pesticides such as dichlofenthion, has toxicity big, and high residue lacks
Point；Medical anthelmintic has albendazole, similarly has certain side effect.
China's Chinese traditional herbs play unquestionable effect in people prevent and cure diseases, and excavate and live from Chinese traditional herbs
Property ingredient be independent intellectual property right new drug development important means and Environment Science, meet International Pharmaceutical Development Trend, have wide
Wealthy application prospect.
Existing research data shows that some phenolic constituents of some Chinese medicines have significant eelworm-killing activity, prompts agricultural
With medical nematicidal drug.It should consider that screening finds eelworm-killing activity phenolic constituent in traditional Chinese medicine, and pass through chemistry side
Method is synthesized.Therefore, exploitation is with hypotoxicity and nematicidal agricultural significant in efficacy is used and medical, to mankind society
There can be significant social and economic benefit foreground.
Invention content
In view of this, the application the present invention provides two kinds of compounds in preparing nematicidal drug.Two kinds of compounds pair
Agriculture nematodiasis and human body parasitic nematode have significant curative effect, and safe, have no toxic side effect.
In order to achieve the above-mentioned object of the invention, the present invention provides following technical scheme：
The present invention provides application of the compound as shown in Formulas I or Formula II in preparing nematicidal drug,
Said medicine chemical name is：Chrysotobibenzyl (chrysotobibenzyl) is colourless acicular crystal, ESI-MS
m/z：[M+Na]+332, molecular formula C19H24O5.Compound source is to pass through the magnificent stem of noble dendrobium (scientific name：Dendrobium sinense
T.Tang et F.T.Wang) extraction separation.
2 ', 4 '-dihydroxy chalcones (2 ', 4 '-dihydroxy chalcone), white amorphous powder, ESI-MS m/
z：[M+Na]+240, molecular formula C15H12O3.Have no that related activity is reported.
The stem of noble dendrobium is first of " Chinese nine big celestial grass ", lightly seasoned micro- salty, and there is invigorating the spleen to promote the production of body fluid, tonifying-Yin and nourishing-stomach, moisten the lung and relieve the cough
Function is important medicine-food two-purpose medicinal material, friendly to human body and Environmental security.
Phytochemistry preparation method：The magnificent stem of noble dendrobium (scientific name：Dendrobium sinense T.Tang et F.T.Wang) it plants
After object dried and crushed, the NaOH solution of pH 9.0-10.0 filters after impregnating 5-10 days, and pH is slowly modulated with HCl solution after filtrate
2.0-6.0, ethyl acetate extraction, ethyl acetate portion living, the materials such as purification on normal-phase silica gel and SephadexLH-20 repeatedly divide by chromatography
It is crystallized from rear precipitation, recrystallization-acquisition monomeric compound after filtering.Detailed process is shown in Fig. 1.
Preferably, nematode is agriculture pathogenic nematode and/or human body parasitic nematode.
Preferably, nematicidal drug further includes pharmaceutically acceptable auxiliary material.
Preferably, pharmaceutically acceptable auxiliary material is one kind or several in disintegrant, lubricant, binder or dispersant
Kind.
Preferably, the dosage form of nematicidal drug is aqua or solid pharmaceutical preparation.
Preferably, solid pharmaceutical preparation is tablet, granule, capsule, powder or pill.
Preferably, compound shown in the Formulas I or Formula II is isolated by being extracted from plant, or pass through chemistry
Synthesis obtains.
Preferably, compound shown in the Formulas I or Formula II is isolated by being extracted from the plant China stem of noble dendrobium.
Preferably, the weight percent that compound shown in Formulas I or Formula II accounts for the nematicidal drug is 1%~99%.
Preferably, the weight percent that compound shown in Formulas I or Formula II accounts for the nematicidal drug is 10%~90%.
Preferably, nematicidal drug further includes other drugs with eelworm-killing activity.
The present invention provides application of two kinds of compounds in preparing nematicidal drug.Two kinds of compounds are Formulas I or Formula II
Shown compound.The technique effect that the present invention has is：
In compound of the present invention and organophosphorus pesticide dichlofenthion and anthelmintic albendazole contrast test, institute of the present invention
It states pharmaceutical activity and is better than dichlofenthion and albendazole, toxicity and residues are less than dichlofenthion and albendazole.
Meanwhile two kinds of compounds to agricultural crops without acute toxicity and long term toxicity poisoning, plant growth is good, no drug
Accumulation.Chemical combination of the present invention is not found in the research to the animal acute toxicity of compound of the present invention and long term toxicity
Object has any adverse reaction, not damaged to each organ.In clinical test, compound of the present invention has parasite patient bright
Aobvious curative effect, and have no toxic side effect and drug dependence.
It is found that the present invention is safe and reliable, can nematodiasis be agriculturally effectively being prevented, it is medical to drive away nematode
Parasite, and have no toxic and side effect to human body and can be widely applied to kill better than existing pesticide and medicine with pharmacological dependence type
In the medicine preparation of nematode.
Description of the drawings
Fig. 1 shows that compound shown in Formulas I and Formula II extracts separation process from the magnificent stem of noble dendrobium.
Specific implementation mode
The invention discloses application of two kinds of compounds in preparing nematicidal drug, those skilled in the art can use for reference
Present disclosure is suitably modified technological parameter realization.In particular, it should be pointed out that all similar substitutions and modifications are to this field skill
It is it will be apparent that they are considered as being included in the present invention for art personnel.The present invention method and application by compared with
Good embodiment is described, related personnel obviously can not depart from the content of present invention, in spirit and scope to as described herein
Methods and applications are modified or suitably change and combine, to realize and apply the technology of the present invention.
In the application for preparing nematicide drug, compound of the present invention can be prepared by this field conventional formulation method
At various agricultural or clinically conventional formulation, for example, can be pharmaceutically acceptable auxiliary to being added under a effective amount of dosage of the present invention
Expect (such as disintegrant, lubricant, binder, dispersant etc.), be prepared into various medicinal preparation for oral administration, the present invention be preferably made tablet,
Granule, capsule, powder, pill or oral solution.
It to those skilled in the art, can be according to conventional formulation method, gently in the case where knowing active constituent
Easy is made various pharmaceutical products, while the auxiliary material employed in preparation is also well known in the art, such as carboxyrnethyl starch sodium, sugarcane
Icing Sugar, honey, sesame oil etc..
The present invention utilizes the Chrysotobibenzyl and 2 ' that plant extract separation method obtains, 4 '-dihydroxy chalcones that can have
Kill agriculture pathogenic nematode and human body parasitic nematode on effect ground, and to the side effect of human body low toxicity and pharmacological dependence type, nematicidal is real
It tests drug effect and is better than existing common pesticides and Western medicine, can be widely applied to agriculture control of nematode and human body parasitic nematode medicine
It is prepared by object.
Two kinds of compounds provided by the invention raw materials used medicine or auxiliary material in the application in preparing nematicidal drug
It is bought by market.
With reference to embodiment, the present invention is further explained：
Embodiment 1：Prepare the agricultural water solvent of compound of the present invention
Raw material (unit is weighed according to weight：g)：Chrysotobibenzyl and 2 ', 4 '-dihydroxy chalcone each 12g, Tween-60 4g
Two parts, two parts of water 100mL.
Two parts of Tween-60s are separately added into 100mL and are heated to 50-60 degrees Celsius, are respectively added slowly to Chrysotobibenzyl and 3 '-
(4- hydroxy phenyls)-propyl alcohol-benzoate, filtering obtain aqueous solution.
The aqueous solution 100mL of preparation can be diluted with water to 4000mL by agricultural for nematicidal, for spraying or rhizosphere note
Enter.
Embodiment 2：Prepare the capsule of compound of the present invention
Each raw material (unit is weighed by following weight：g)：Chrysotobibenzyl and 2 ', 4 '-each 50g of dihydroxy chalcone.
By Chrysotobibenzyl and 2 ', 4 '-dihydroxy chalcones are separately added into ethyl alcohol 100mL, and carboxyrnethyl starch sodium is added in filtering
1.8g is mixed well, and particle is made in spray drying, is packed into No. 1 capsule to get capsule.
Embodiment 3：Prepare the tablet of compound of the present invention
Each raw material (unit is weighed by following weight：g)：Chrysotobibenzyl and 2 ', 4 '-each 50g of dihydroxy chalcone.
By Chrysotobibenzyl and 2 ', 4 '-dihydroxy chalcones are separately added into ethyl alcohol 100mL, and carboxyrnethyl starch sodium is added in filtering
1.8g is mixed well, and particle is made in spray drying, send to tabletting machine to obtain the final product.
Embodiment 4：Prepare the pill of compound of the present invention
Each raw material (unit is weighed by following weight：g)：Chrysotobibenzyl and 2 ', 4 '-each 50g of dihydroxy chalcone.
By Chrysotobibenzyl and 2 ', 4 '-dihydroxy chalcones are separately added into ethyl alcohol 100mL, and carboxyrnethyl starch sodium is added in filtering
1.8g is mixed well, and particle is made in spray drying, is subsequently added into pure sesame oil or honey 20g mixings, send to centrifugation and make ball machine
Pill is made.
Embodiment 5：The eelworm-killing activity of compound of the present invention
Eelworm-killing activity is by the killing activity to Panagrellus redivivus, and safety is evaluated with cytotoxic activity.
All compounds or sample to be measured are dissolved in 10 μ L dimethyl sulfoxides, then use water (Tween- containing 0.3%v/v
20) a concentration of 25mg/mL storage solutions are diluted to.Nematode is in oat medium (oatmeal 20g, water 20mL, in 200mL tapers
In bottle, 121 DEG C of steam sterilizings 30 minutes) in 28 DEG C of hatching cultures 5-6 days.Then it is filled and is prepared with the culture dish of a 6cm diameter
300 μ L nematodes suspension (about 200 half adult nematodes).Storing solution to be measured is added and gently mixes thoroughly and make to be measured
Compound is that 25 μ g/mL (survey median effective dose IC50With a concentration of 0.2,1,5,25, and 125 μ g/mL).With dimethyl Asia
Sulfone (10 μ L) is dissolved in water (Tween-20 containing 0.3%v/v) and is used as blank control.Each test, survey repeat three times.
The opposite nematode lethality (NA) of eelworm-killing activity counts dead under the microscope after being cultivated 24 hours for 28 DEG C
Nematode number (n>100) it obtains.NA passes through formula NA=DN/SN × 100% (the nematode number of DN death；The institute that SN is counted is wired
Borer population mesh, SN>100) it calculates.Absolute nematode lethality RDR passes through formula RDR=NAn-NA0(NAnThe opposite nematode of compound causes
Dead rate, NA0It is the relative lethality of blank control).If the absolute nematode lethality of any compound is more than 40%, it is necessary to
Test concentrations gradient (IC50With a concentration of 0.2,1,5,25, and 125 μ g/mL) absolute lethal rate and with Reed and Muench
Method calculates the median effective dose IC of this compound50。
The anti-eelworm-killing activity of 1. Compound ira vitro of table
By table 1 the results show that Chrysotobibenzyl and 2 ', 4 '-dihydroxy chalcones show very strong nematicide work
Property, than existing organophosphorus insecticidal nematode pesticide dichlofenthion and people with anthelmintic albendazole also than get well, EC50Value respectively reaches 6.58
And 3.33mM, toxicity is again than the minimum positive, CC low to albendazole50It is better to make compound have more than 50mM
Safety.This illustrates that compound has external eelworm-killing activity and good safety well.
Embodiment 6：The field experiment of compound formulation of the present invention
The cucumber for suffering from nematodiasis, tomato, eggplant and each 50 plants of agalloch eaglewood seedling are taken, plant strain growth is thin and weak, and blade-section falls off,
Partial blade turns to be yellow.
1, implementation：Giving invention drug by strain 20mL, (compound stock solutions prepared by embodiment 1, are diluted to
2000mL)
2, effect assessment standard：Plant strain growth situation is seen after 5 days, and Rhizosphere sampling is taken to detect rhizosphere nematode number, it is positive right
According to for dichlofenthion.
Effectively：Plant strain growth restores, blade greening, and rhizosphere nematode disappears.
Part is effectively：Plant strain growth fails to restore or death, rhizosphere nematode disappear.
In vain：Plant strain growth fails to restore or death, rhizosphere nematode do not disappear.
Residual：Take Rhizosphere sampling 5g after 10 days, after water muddiness, ethyl acetate extraction uses gas chromatography-mass spectrometry after concentration
Residual is quantitatively detected with (Gas chromatography-mass spectrum, GC-MS) technology.
3, result：The prepared medicament of compound can effectively kill rhizosphere in most cases and endanger nematode, make plant
Strain restoration ecosystem, a small number of plant may be deeper due to eelworm harm, fails recovery or dead, shows as part effectively, Shao Liangzhi
Strain is dead before medicament action, and it is invalid to show as.Compound prepares medicament and residual is not detected.
The anti-eelworm-killing activity experiment in 2. compound crop field of table
Embodiment 7：Toxicity of compound research of the present invention
1, studies on acute toxicity
Kunming mouse is taken, drug of the present invention (the compound capsule inner powder prepared by embodiment 2 is given by 1g/kg gavages
End), then 1 day successive administration 4 times gives normal diet per minor tick 6h, carry out pathologic inspection to each organ, do not send out
Existing organ disease.
2, long term toxicity is studied
Kunming mouse is taken, in pressing, large dosage of group (1g/kg, 2g/kg) gavage gives drug of the present invention (embodiment 2 is made
Powder in standby compound capsule), 1 time a day, successive administration measures mouse weight, heart function, liver function, kidney function after 14 days
The indexs such as energy, electrocardiogram, administration group compared with the control group, are shown no obvious abnormalities respectively.The pathological examination heart, liver,kidney,spleen, lung,
The internal organs such as Stomach duodenum, large intestine, small intestine, adrenal gland and genitals, administration group compared with the control group, are showed no apparent respectively
Poisoning sexually revises.The above result shows that compound of the present invention is safe and non-toxic, it can be used for clinic.
Embodiment 8：Two kinds of compound formulations of the present invention have carried out clinical test respectively
1, subjects data
Chrysotobibenzyl is 40 patients：Age 5-33 Sui；Male 22, women 18；2 ', 4 '-dihydroxy chalcones：For
40 patients, age 5-33 Sui, male 20, women 20；The course of disease -2 years 2 weeks；Main performance is that appetite is bad, abdominal pain, or
Diarrhea, constipation, and the diseases such as there is uneasiness, irritability, easily shy, grind one's teeth in sleep, all to have the above symptom, excrement detects visible roundworm egg, i.e.,
Meet the clinical diagnosis of roundworm.
2, therapy and the standard of curative effect evaluation：Compound capsule (embodiment 2) of the present invention takes orally, and dosage is
300mg/ days, child halved within 12 years old or less, was once taken before sleeping every night, totally two courses for the treatment of.
3, criterion of therapeutical effect：The roundworm corpse of expeling can be seen after an action of the bowels greatly, and detect treatment after patient stool in roundworm
Whether ovum, ill symptoms disappear.
Effectively：Second day and third day stool roundworm as it can be seen that treatment after patient stool in roundworm egg it is invisible, bad disease
Whether shape disappears.
Part is effectively：Second day with third day stool roundworm as it can be seen that the roundworm egg after treatment in patient stool is still visible.
In vain：Roundworm is had no with third day stool within second day, the roundworm egg after treatment in patient stool is still visible.
4, clinical effectiveness
One, clinical cardinal symptom sign improves in 40 patients of situation, is not hospitalized.
Two, various inspection results
Chrysotobibenzyl：In 40 patients, fail to detect roundworm egg in stool after 40 medications, wherein 37 visible
Roundworm corpse, 38 ill symptoms disappear, 2 improvements.
2 ', 4 '-dihydroxy chalcones：In 40 patients, fail to detect roundworm egg in stool after 40 medications,
In 39 visible roundworm corpse, 38 ill symptoms disappear, 1 improvement.
Three, clinical effectiveness summarizes 40 through clinical definite roundworm infection patient, through selecting two kinds of compound capsule treatments.
1, two kinds of compound capsules are respectively to 40 roundworm infection clinical treatment comprehensive observings, the results showed that, this medicine is to ascarid
Insect infection treatment has clear curative effect.
2, toxic side effect observes result：There is any adverse reaction without an example patient in two groups of 40 patients treated,
Illustrate that drug of the present invention is safe to human body.
Above-mentioned clinical observation result shows that the compounds of this invention is significant in efficacy for treating roundworm infection, has no toxic side effect,
Without drug dependence.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, various improvements and modifications may be made without departing from the principle of the present invention, these improvements and modifications are also answered
It is considered as protection scope of the present invention.
Claims (10)
1. application of the compound as shown in Formulas I or Formula II in preparing nematicidal drug,
2. application according to claim 1, which is characterized in that the nematode is that agriculture pathogenic nematode and/or human body are parasitic
Nematode.
3. application according to claim 1, which is characterized in that the nematicidal drug further includes pharmaceutically acceptable auxiliary
Material.
4. application according to claim 1, which is characterized in that the pharmaceutically acceptable auxiliary material is disintegrant, lubrication
One or more of agent, binder or dispersant.
5. application according to claim 1, which is characterized in that the dosage form of the nematicidal drug is aqua or solid system
Agent.
6. application according to claim 5, which is characterized in that the solid pharmaceutical preparation is tablet, granule, capsule, dissipates
Agent or pill.
7. application according to claim 1, which is characterized in that compound passes through from plant shown in the Formulas I or Formula II
It extracts isolated, or is obtained by chemical synthesis.
8. application according to claim 1, which is characterized in that compound shown in the Formulas I or Formula II accounts for the nematicidal
The weight percent of drug is 1%~99%.
9. application according to claim 1, which is characterized in that compound shown in the Formulas I or Formula II accounts for the nematicidal
The weight percent of drug is 10%~90%.
10. application according to claim 1, which is characterized in that the nematicidal drug further includes other with nematicidal
Active drug.
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| US20160174554A1 (en) * | 2014-12-18 | 2016-06-23 | Derivados Biotecnologicos Sac Derbiotec | Compostion and method for the control of phyto-parasitic nematodes |
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| US20160174554A1 (en) * | 2014-12-18 | 2016-06-23 | Derivados Biotecnologicos Sac Derbiotec | Compostion and method for the control of phyto-parasitic nematodes |
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