WO1992019616A1 - Improvements of a pesticidal/insect repellent comprising synthesis of a new pesticidal insect repellent - Google Patents

Improvements of a pesticidal/insect repellent comprising synthesis of a new pesticidal insect repellent Download PDF

Info

Publication number
WO1992019616A1
WO1992019616A1 PCT/AU1992/000200 AU9200200W WO9219616A1 WO 1992019616 A1 WO1992019616 A1 WO 1992019616A1 AU 9200200 W AU9200200 W AU 9200200W WO 9219616 A1 WO9219616 A1 WO 9219616A1
Authority
WO
WIPO (PCT)
Prior art keywords
pesticidal
extracts
insect repellent
derivatives
neem
Prior art date
Application number
PCT/AU1992/000200
Other languages
French (fr)
Inventor
Vincent Henry Guerrini
Original Assignee
Vincent Henry Guerrini
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 Vincent Henry Guerrini filed Critical Vincent Henry Guerrini
Publication of WO1992019616A1 publication Critical patent/WO1992019616A1/en

Links

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
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08—Magnoliopsida [dicotyledons]
    • A01N65/26—Meliaceae [Chinaberry or Mahogany family], e.g. mahogany, langsat or neem
    • 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
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • 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
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/40—Liliopsida [monocotyledons]
    • A01N65/44—Poaceae or Gramineae [Grass family], e.g. bamboo, lemon grass or citronella grass
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J15/00—Stereochemically pure steroids containing carbon, hydrogen, halogen or oxygen having a partially or totally inverted skeleton, e.g. retrosteroids, L-isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C07J71/001—Oxiranes
    • C07J71/0021—Oxiranes at position 14(15)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings

Definitions

  • the present invention relates to improvements of pesticidal compositions comprising methods to synthesize or produce a new pesticidal/insect repelling substance.
  • Patent application 26320/88 the present applicant describes the use of azadirachtin rich extracts of neem seeds and other meliaceous plants to inhibit pests such as blowfly larvae, lice and fleas.
  • Azadirachin rich extracts from neem seeds have been used in Indian folk medicine for thousands of years and this, together with recent laboratory tests has shown neem seed extracts or meliaceous extracts with azadirachtin to be of very low toxicity to vertebrates.
  • the present invention thus provides a new pesticidal/ insect repellent substance and an improved pesticidal/insect repellent mixture by mixing 1 to 35% by volume of oil of citronella, from 2 to 30g per litre azadirachtin, from 30 to 200g per litre neem seed extract or extract of meliaceous plants containing 5% azadirachtin, from 30 to 200g per litre diethyl toluamide (DEET), from 6 to 46g per litre di-n-propyl isochinchomerate.
  • DEET diethyl toluamide
  • the invention also relates to a method of killing or repelling pests comprising applying the mixture and new molecule to the pests or their surroundings.
  • the substances may be applied together or sequentially.
  • the invention also relates to a method of synthesizing Azadirachtins, nimbidens, protoliminoids, liminoids, or tetratriterpenoids, pentanortriterpernoids, including meliantrol, nimbocinone, azadirachtol and azadirachnol or changing the structure of the compounds shown on Drawing 1, page 1/3, present in extracts of meliaceous trees including neem tree extracts (Azadirachta Indica A.Juss.) or which have been synthesized artificially.
  • the invention also relates to a method or a process to increase the concentrations of the aforementioned substances present in meliaceous tree extracts including neem tree and seed extracts namely the tetratriterpenoids, pentanortriterpenoids, hexatriterpenoids, azadirachtins, salanninns, azadiradiones. nimidens and vilanisin and derivatives. These substances are illustrated on Drawing 1. page 1/3.
  • the invention also relates to a method or process to unbind or release the aforementioned substances illustrated on Drawing 1, page 1/3 from proteins, fats, oils or any other substances to which the substances illustrated on Drawing 1, page 1/3 bind in the extracts of meliaceous trees including neem seeds and extracts.
  • the invention also relates to a process or method to improve the pesticidal and insect repellent properties of the substances illustrated on Drawing l, page 1/3.
  • the invention also relates to a method to change the structure of the substances shown on Drawing 1, page 1/3, wherein the extracts of meliaceous trees including neem seed extracts are heated in absence or presence of air to between 30oC and 200oC for periods ranging between 1 second and 1000 hours.
  • the invention relates to a process or method to increase the concentrations, to unbind and improve the pesticidal and insect inhibiting properties of the substances shown on Drawing l page 1/3 wherein the extracts of meliaceous trees including neem tree and seeds extracts are heated in the presence or absence of air to between 30oC and 200oC for periods ranging between 1 second and 1000 hours.
  • composition may be made by mixing the following:-
  • Alcohol e.g. Ethanol
  • Samples 1 or Samples 2 were blended with 10 grams of food containing 50 first stage larvae of the insect Lucilia cuprina. Each drop contained 5 microlitres (ul) of liquid.
  • azadirachtins nimbins, triterpernoids, pentatriterpernoids, salannins vilasinins, liminoids in neem seed extracts heated between 30oC and 70oC for 1 second to 1000hours.
  • Drawing 2 on page 2/3 shows the tracings representing the concentration of azadirachtin and other substances in meliaceous extracts in samples 1 kept at 4oC for 14 days .
  • Drawing 3 on page 3/3 shows the tracings representing the concentration of azadirachtin and other substances in meliaceous extracts in this case neem seed extract in Samples 2 kept at 54oC for 14 days

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Mycology (AREA)
  • Microbiology (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Biotechnology (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

There is provided a novel method to improve the pesticidal and repellent properties of neem extracts or azadirachtin containing compositions comprising the synthesis of a new pesticide repellent. Neem extracts containing azadirachtins or compositions containing neem extracts or neem extracts with azadirachtins, dialkyltoluamides and volatile oils are heated between 30 and 200 degrees centigrade from 1 second to 1000 hours to improve the pesticidal and repellent properties of the compositions or synthesize new pesticides or insect repellents.

Description

IMPROVEMENTS OF A PESTICIDAL/INSECT REPELLENT COMPRISING SYNTHESIS OF A NEW PESTICIDAL INSECT REPELLENT.
The present invention relates to improvements of pesticidal compositions comprising methods to synthesize or produce a new pesticidal/insect repelling substance.
In Australian Patents 608281, 608564, 607922, and
Patent application 26320/88, the present applicant describes the use of azadirachtin rich extracts of neem seeds and other meliaceous plants to inhibit pests such as blowfly larvae, lice and fleas.
Azadirachin rich extracts from neem seeds have been used in Indian folk medicine for thousands of years and this, together with recent laboratory tests has shown neem seed extracts or meliaceous extracts with azadirachtin to be of very low toxicity to vertebrates.
It is an object of this invention to provide a new hereto unknown pesticidal/insect repelling substance and to provide a method to synthesize or produce the new insect or pest inhibiting substance. It is a further object of this invention to provide a method to improve the insecticidal/insect repelling properties of the pesticidal composition described in Patent PCT/AU90/00586.
The present invention thus provides a new pesticidal/ insect repellent substance and an improved pesticidal/insect repellent mixture by mixing 1 to 35% by volume of oil of citronella, from 2 to 30g per litre azadirachtin, from 30 to 200g per litre neem seed extract or extract of meliaceous plants containing 5% azadirachtin, from 30 to 200g per litre diethyl toluamide (DEET), from 6 to 46g per litre di-n-propyl isochinchomerate. from 1.5 to 10.5g per litre N-Octyl bicycloheptene dicarboximide, from 0.17 to 1.16 g per litre Triclosan and alcohol and lemon grass oil the remainder, and heating the mixture to between 30 and 200 ºC from 1 second to 1000 hours.
The invention also relates to a method of killing or repelling pests comprising applying the mixture and new molecule to the pests or their surroundings. The substances may be applied together or sequentially.
The invention also relates to a method of synthesizing Azadirachtins, nimbidens, protoliminoids, liminoids, or tetratriterpenoids, pentanortriterpernoids, including meliantrol, nimbocinone, azadirachtol and azadirachnol or changing the structure of the compounds shown on Drawing 1, page 1/3, present in extracts of meliaceous trees including neem tree extracts (Azadirachta Indica A.Juss.) or which have been synthesized artificially.
The invention also relates to a method or a process to increase the concentrations of the aforementioned substances present in meliaceous tree extracts including neem tree and seed extracts namely the tetratriterpenoids, pentanortriterpenoids, hexatriterpenoids, azadirachtins, salanninns, azadiradiones. nimidens and vilanisin and derivatives. These substances are illustrated on Drawing 1. page 1/3.
The invention also relates to a method or process to unbind or release the aforementioned substances illustrated on Drawing 1, page 1/3 from proteins, fats, oils or any other substances to which the substances illustrated on Drawing 1, page 1/3 bind in the extracts of meliaceous trees including neem seeds and extracts.
The invention also relates to a process or method to improve the pesticidal and insect repellent properties of the substances illustrated on Drawing l, page 1/3.
The invention also relates to a method to change the structure of the substances shown on Drawing 1, page 1/3, wherein the extracts of meliaceous trees including neem seed extracts are heated in absence or presence of air to between 30ºC and 200ºC for periods ranging between 1 second and 1000 hours.
The invention relates to a process or method to increase the concentrations, to unbind and improve the pesticidal and insect inhibiting properties of the substances shown on Drawing l page 1/3 wherein the extracts of meliaceous trees including neem tree and seeds extracts are heated in the presence or absence of air to between 30ºC and 200ºC for periods ranging between 1 second and 1000 hours.
Further embodiments of the invention shall become apparent from reference to the examples.
Example A
one litre of a liquid pesticidal/insect repelling
composition may be made by mixing the following:-
Oil of citronella 10 to 350ml
Meliaceous extracts
containing 5% azadirachtin 40 to 600ml or pure azadirachtin 2 to 30g
Triclosan 0.17 to 1.16g
N,N,Diethyl-M-Toluamide 30 to 200g
Di-N-propyl Isochinchomerate 6 to 46g
Alcohol (e.g. Ethanol) Remainder
Lemon Grass oil Traces
Comparitive Example 1a
Four samples of the mixture were kept at 4ºC for 14 days {Samples 1) and four samples were kept at 54ºC for 14 days (Samples 2).
0, 5, 20, 60, and 100 drops respectively, of Samples 1 or Samples 2 were blended with 10 grams of food containing 50 first stage larvae of the insect Lucilia cuprina. Each drop contained 5 microlitres (ul) of liquid.
Larval length or growth and larval survival in food blended with Samples 1 or Samples 2 are set out in Table la on the next page of this description.
Table 1a
Drops (number) 0 5 20 60 100
Dose (ul) 0 25 100 300 500
Samples 1$
Mixture stored at
4ºC for 14 days
Larvae Length(mm) 8.0+0.3 6.8+0.5 3.3+0.3 1.2+0.8 0 Survival (%) 96 86 43 12 0
Samples 2$
Mixture stored at
54ºC for 14 days
Larvae Length(mm) 8.0+0.3 3.2+0.2* 0* 0* 0* Survival (%) 96 11 0 0 0
$ = All tests duplicated (ie:Four samples for each concentration n=4) * = P< 0.05 larval length and survival was
significantly less in samples 2 compared to samples 1 (Two -way analysis of variance).
From a comparison of results in Table la it is apparent that heating at 54ºC for 14 days increased the pesticidal/insect inhibiting properties of the mixture. In fact, heating increased efficiency 53 to 100% over the range of concentrations tested.
Table 1b
Concentration of Active constituents including
azadirachtins, nimbins, triterpernoids, pentatriterpernoids, salannins vilasinins, liminoids in neem seed extracts heated between 30ºC and 70ºC for 1 second to 1000hours.
0 seconds 1000 hours
Concentration (5.) 1 5
A comparison of results in the table 1b shows that the concentration of the actives in neem seeds extracts increased five fold when exposed to heating.
Comparative example 1b
Drawing 2 on page 2/3 (drawings) shows the tracings representing the concentration of azadirachtin and other substances in meliaceous extracts in samples 1 kept at 4ºC for 14 days .
Drawing 3 on page 3/3 (drawings) shows the tracings representing the concentration of azadirachtin and other substances in meliaceous extracts in this case neem seed extract in Samples 2 kept at 54ºC for 14 days
From a comparison of Drawing 2 and Drawing 3 it is apparent that heating the pesticidal/insect repellent mixture created a new unknown substance.

Claims

THE CLAIMS DEFINING THE INVENTION ARE AS FOLLOWS:
1. Derivatives of nimbin, nimbinin, meliantrol, azadirachtol, azadirone, azadirachtins A to G, salannins, salannolides, desacetyl-nimbilonides, nimolicilinoic acids, protoliminoids, liminoids, tetratriterpenoids, pentanortriterpenoids and hexatriterpenoids present in extracts obtained from meliaceous trees including neem tree and seed extracts
2. Derivatives of oil of citronella
3. Derivatives of diethyl methyl toluamides.
4. A process or method to synthesize derivatives of nimbin, meliantrol, azadirachtois, azadirachtins A to G, salannins, salannilides, desacetylnimbilonides, nimolicilinoic acids, protoiminoids, liminoids, tetratriterpenoids, pentanortriterpenoids, or oil of citronella or diethyl-methyl -toluamides.
5. A process or method to release from binding the substances mentioned in Claims 1 to 4.
6. A process or method to change the structure of the substances mentioned in Claims 1 to 4
7. A method or process to increase the concentration of the substances present in neem seed extracts mentioned in Claims 1 to 4.
8. A method or process to synthesize a new pesticidal/insect inhibiting substance.
PCT/AU1992/000200 1991-05-06 1992-05-01 Improvements of a pesticidal/insect repellent comprising synthesis of a new pesticidal insect repellent WO1992019616A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AUPK597091 1991-05-06
AUPK5970 1991-05-06

Publications (1)

Publication Number Publication Date
WO1992019616A1 true WO1992019616A1 (en) 1992-11-12

Family

ID=3775384

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/AU1992/000200 WO1992019616A1 (en) 1991-05-06 1992-05-01 Improvements of a pesticidal/insect repellent comprising synthesis of a new pesticidal insect repellent

Country Status (1)

Country Link
WO (1) WO1992019616A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0695746A2 (en) * 1994-08-01 1996-02-07 Pharma Mar, S.A. Antiviral compounds and pharmaceutical compositions
US6733802B1 (en) 1997-12-17 2004-05-11 Fortune Bio-Tech Limited Natural azadirachtin composition

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0308044A2 (en) * 1987-07-14 1989-03-22 Native Plants Incorporated Azadirachtin derivative insecticides
AU2344588A (en) * 1987-10-06 1989-04-06 Dow Agrosciences Llc Insecticidal hydrogenated neem extracts
US4902713A (en) * 1987-01-26 1990-02-20 Max-Planck-Gesellschaft Zur Foederung Der Wissenschaften E.V. Azadirachtin-like compounds and insect-destroying agents containing them

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4902713A (en) * 1987-01-26 1990-02-20 Max-Planck-Gesellschaft Zur Foederung Der Wissenschaften E.V. Azadirachtin-like compounds and insect-destroying agents containing them
EP0308044A2 (en) * 1987-07-14 1989-03-22 Native Plants Incorporated Azadirachtin derivative insecticides
AU2344588A (en) * 1987-10-06 1989-04-06 Dow Agrosciences Llc Insecticidal hydrogenated neem extracts

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
HETEROCYCLES, Vol. 28, No. 1, 1989, INADA et al., "Phytochemical studies on melicaceous plants, structure of a new apotircuallane - type triterpene, 21-0-methyl toosendanpentol from fruits of melia-toosendan sieb". *
HETEROCYCLES, Vol. 29, No. 1, 1989, pp. 87-96, SIDDIQUI et al., "Tetranortriterpenoids from Azadriachta Indica A. Juss (Meliaceae)". *
JOURNAL OF NATURAL PRODUCTS, Vol. 51, No. 1, pp. 30-43, 1988, SIDDIQUI et al., "Tetracyclic triterpenoids and their derivatives from azadirachta indica". *
JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANS, Vol. 1, pp. 1429-32, 1987, SIDDIQUI et al.: "Studies in the chemical constituents of azadirachta indica A. Juss (Meliaceae). Part 10, Isolation and structure elucidation of isonimolicinolide, the first 17-acetoxy tetranorter-penoid and nimolicinoil acid, the first hexanortriterpenoid with an apoeuphane (Apotirucallane) skeleton". *
PHYTOCHEMISTRY, Vol. 27, No. 12, pp. 3903-3907, 1988, SIDDIQUI et al., "Phenolic Tricyclic Diterpenoids from the Bark of Azadirachta Indica". *
PHYTOCHEMISTRY, Vol. 29, No. 12, pp. 3963-3965, 1990, GAIKWAD et al.: "Nimbocinol and 17-Epinimbocinol from the Nimbidin Fraction of Neem Oil". *
TETRAHEDRON, Vol. 43, No. 12, pp. 2805-2815, 1987, BILTON et al., "An x-ray crystallographic, mass spectrocopic, and NMR study of the liminoid insect antifeedant azadirachtin and related derivatives". *
TETRAHEDRON, Vol. 43, No. 12, pp. 2817 to 2830, 1987, KRAUS et al., "Structure determination by NMR of Azadirachta indica A. Juss (Meliaceae)". *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0695746A2 (en) * 1994-08-01 1996-02-07 Pharma Mar, S.A. Antiviral compounds and pharmaceutical compositions
EP0695746A3 (en) * 1994-08-01 1996-08-21 Pharma Mar Sa Antiviral compounds and pharmaceutical compositions
US6733802B1 (en) 1997-12-17 2004-05-11 Fortune Bio-Tech Limited Natural azadirachtin composition

Similar Documents

Publication Publication Date Title
Thorsell et al. Repelling properties of some plant materials on the tick Ixodes ricinus L.
Patil et al. Bioefficacy of Plumbago zeylanica (Plumbaginaceae) and Cestrum nocturnum (Solanaceae) plant extracts against Aedes aegypti (Diptera: Culicide) and nontarget fish Poecilia reticulata
Pavela et al. Mosquitocidal activities of thyme oils (Thymus vulgaris L.) against Culex quinquefasciatus (Diptera: Culicidae)
Omar et al. Antifeedant activities of terpenoids isolated from tropical Rutales
Komansilan et al. Isolation and identification of biolarvicide from soursop (Annona muricata Linn) seeds to mosquito (Aedes aegypti) larvae
Elango et al. Efficacy of medicinal plant extracts against Formosan subterranean termite, Coptotermes formosanus
Ghabbari et al. Behavior-modifying and insecticidal effects of plant extracts on adults of Ceratitis capitata (Wiedemann)(Diptera Tephritidae)
MX2011010032A (en) Pesticide made of isoquinoline alkaloids, flavonoids and vegetable and/or essential oils.
de Santana Campos et al. Acaricidal properties of vetiver essential oil from Chrysopogon zizanioides (Poaceae) against the tick species Amblyomma cajennense and Rhipicephalus (Boophilus) microplus (Acari: Ixodidae)
Nicoletti et al. Neem-borne molecules as eco-friendly control tools against mosquito vectors of economic importance
Ali et al. Chemical composition and biological activity of essential oils from four Nepeta species and hybrids against Aedes aegypti (L.)(Diptera: Culicidae).
Hannour et al. Chemical composition and toxicity of Moroccan Rosmarinus officinalis (Lamiaceae) essential oils against the potato tuber moth, Phthorimaea operculella (Zeller, 1873) Zeller (Lepidoptera, Gelechiidae)
KR101174042B1 (en) Mixture extract having insecticidal and repellent effects and products using the same
Okonkwo et al. Insecticidal potentials and chemical composition of essential oils from the leaves of Phyllanthus amarus and Stachytarpheta cayennensis in Nigeria
Hashemi et al. Insecticidal Activity of Essential Oil from Juniperus communis L. subsp. hemisphaerica (Presl) Nyman against Two Stored Product Beetles.
KR100868314B1 (en) Natural insecticide composition containing bisabolangelone and derivative thereof
Majumder et al. GC-MS analysis reveals Dendrobium candidum is a mosquito-attractant orchid with mosquitocidal compounds
WO1992019616A1 (en) Improvements of a pesticidal/insect repellent comprising synthesis of a new pesticidal insect repellent
Tabanca et al. Chemical composition, biting deterrent, antimalarial and antimicrobial activity of essential oil from Hypericum scabrum L.
Ghosh et al. Leaves and barks of Albizia shade trees in tea plantation shows both insect attractant and pesticidal properties: a GC-MS based investigation
Aboelhadid et al. Synergistic larvicidal and repellent effects of essential oils of three Origanum species on Rhipicephalus annulatus tick
Kouninki et al. Biological activities of Cassia mimosoides, Eucalyptus camaldulensis, Vepris heterophylla plant extract toward old larvae and adults of Tribolium castaneum (Coleoptera: tenebrionidae)
KR100484887B1 (en) Natural composition of repelling mosquitoes
vama Etienne et al. Repellent effect of some essential oil from Ivorian ethnomedicinal plant against malaria vector, Anopheles gambiae (Giles, 1902)
MEKONNEN et al. Adaptation of citronella grass oil (Cymbopogon Winterianus Jowitt) Tecnologies as an alternative method for cockroaches (Blattella Germanica L.) repellant

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AT AU BB BG BR CA CH CS DE DK ES FI GB HU JP KP KR LK LU MG MN MW NL NO PL RO RU SD SE US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE BF BJ CF CG CH CI CM DE DK ES FR GA GB GN GR IT LU MC ML MR NL SE SN TD TG

NENP Non-entry into the national phase

Ref country code: CA

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642