WO1997016975A1 - Herbicidal composition and method - Google Patents

Herbicidal composition and method Download PDF

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Publication number
WO1997016975A1
WO1997016975A1 PCT/AU1995/000739 AU9500739W WO9716975A1 WO 1997016975 A1 WO1997016975 A1 WO 1997016975A1 AU 9500739 W AU9500739 W AU 9500739W WO 9716975 A1 WO9716975 A1 WO 9716975A1
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WO
WIPO (PCT)
Prior art keywords
oil
terpene
derivative
terpene compound
limonene
Prior art date
Application number
PCT/AU1995/000739
Other languages
French (fr)
Inventor
John Selga
Wayne Andrew Kiely
Original Assignee
John Selga
Wayne Andrew Kiely
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
Priority to AUPM5529A priority Critical patent/AUPM552994A0/en
Priority claimed from AUPM5529A external-priority patent/AUPM552994A0/en
Priority to AU17959/95A priority patent/AU699468B2/en
Application filed by John Selga, Wayne Andrew Kiely filed Critical John Selga
Priority to PCT/AU1995/000739 priority patent/WO1997016975A1/en
Priority claimed from US09/068,355 external-priority patent/US5998335A/en
Publication of WO1997016975A1 publication Critical patent/WO1997016975A1/en

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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08Magnoliopsida [dicotyledons]
    • A01N65/36Rutaceae [Rue family], e.g. lime, orange, lemon, corktree or pricklyash
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N27/00Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/04Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/06Oxygen or sulfur directly attached to a cycloaliphatic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/06Coniferophyta [gymnosperms], e.g. cypress
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08Magnoliopsida [dicotyledons]
    • A01N65/28Myrtaceae [Myrtle family], e.g. teatree or clove

Abstract

The present invention relates to a herbicidal composition having, as an active ingredient, a terpene compound, a terpene derivative, or an essential oil comprising a terpene compound or derivative. In particular, the herbicidal composition will comprise a pine oil, a citrus oil or a terpene compound or derivative derived from pine oil or citrus oil. In a further aspect, the invention provides a method for controlling unwanted plant growth, wherein a terpene compound or derivative, an essential oil comprising a terpene compound or derivative, or a herbicidal composition having, as an active ingredient, a terpene compound or derivative or an essential oil comprising a terpene compound or derivative is applied to the unwanted plant or plants.

Description

HERBICIDAL COMPOSITION AND METHOD

BACKGROUND TO THE INVENTION

The present invention relates to a herbicidal composition having, as an active ingredient, a terpene compound, a terpene derivative, or an essential oil comprising a terpene compound or derivative. In particular, the herbicidal composition will comprise a pine oil, dipentene, pinene, a pine alcohol or a terpene compound or derivative derived from pine oil. A citrus oil or a terpene compound derived from citrus oil, e.g. limonene ( l-methyl-4-( 1-methylethenyl)- cyclohexene) , may also be used.

Many herbicidal compositions presently on the market are highly toxic to humans and domestic animals. A herbicide having lower toxicity is desirable, particularly for use by the home gardener.

The active ingredient of the present herbicidal compositions has the advantage of being an environmentally friendly, natural product, which is unlikely to cause environmental pollution or create toxicity problems for humans or domestic animals .

SUMMARY OF THE INVENTION

The present invention provides a herbicidal composition, having as an active ingredient a terpene compound or derivative, which may be either naturally occurring or synthetic. (Natural pine oil, for example, is virtually unobtainable. )

Although the terpene compounds or derivatives are believed to be the active ingredients of the herbicidal compositions, the same herbicidal effect is found using "whole" essential oils, such as pine oils and citrus oils, comprising such terpene compounds or derivatives. The addition of other essential or natural oils can enhance the activity of the preparation.

In a further aspect, the invention provides a method for controlling unwanted plant growth, wherein a terpene compound or derivative, an essential oil comprising a terpene compound or derivative, or a herbicidal composition having, as an active ingredient, a terpene compound or derivative or an essential oil comprising a terpene compound or derivative is applied to the unwanted plant or plants.

DETAILED DESCRIPTION OF THE INVENTION

The active ingredient of the present herbicidal compositions is a naturally occurring or synthetic terpene (e.g. dipentene, limonene or pinene) or terpene derivative (e.g. terpineol or a pine alcohol), or an essential oil (e.g. a pine or citrus oil), in either pure or diluted form. Examples of suitable citrus oils are orange, lemon, grapefruit, mandarin, tangerine or tangelo oil, and in particular orange oil.

Although the preferred active ingredient is a pine oil or a terpene compound or derivative derived from pine oil, other essential oils, terpenes and terpene derivatives may also be effective, e.g. citrus oils, citrus oil derivatives, terpenes or terpene derivatives derived from citrus oils, tea tree oil (Oil of Melaleuca) and eucalyptus oil. The major terpene derivative present in pine oil is terpineol. As with pine oil, the major terpene derivatives present in tea tree oil and eucalyptus oil are alcohol compounds, being terpinen-4-ol and cineole (eucalyptol) respectively.

In particular, dipentene, which is a synthetic derivative of pine oil predominantly comprising d,1-limonene, has been found to be effective. In a preferred embodiment, the major active component of the herbicidal compositions is pine oil, a pine alcohol, pinene, dipentene or d-limonene. The last-mentioned compound is found in many essential oils and is the major active component of citrus oils .

1-Limonene has also been trialled, and appears to be as herbicidally-effective as d-limonene.

Tea tree and eucalyptus oils display very high herbicidal activity, but are currently high cost materials available in limited volumes. Therefore, until prices drop with increased world production, it is preferred that these oils be incorporated in the herbicidal compositions of the present invention as minor additives . Both tea tree oil and eucalyptus oil were found to enhance the herbicidal activity of an emulsion of pine oil when added at concentrations as low as 1.5% by volume. If appears that they have a synergistic effect when added to pine oil.

The herbicidal compositions of the present invention are non- selective, non-systemic herbicides, which are effective against almost any vegetation, and specifically against common crop and garden weeds, both annual and perennial . They are "knock-down" herbicides, which must be sprayed over a substantial portion of the above-ground part of the plant, in order to have effect. Conveniently, the herbicides are applied as a fine droplet spray. The non-systemic nature of the present herbicidal compositions is a considerable advantage to the home gardener, as spray drift is unlikely to cause problems. If a small amount of the herbicidal composition lands on a wanted plant, that plant is unlikely to be killed or badly damaged. A further consequence of the non-systemic nature of the herbicide is that the weed does not have to be in an active growth stage, in order for the herbicide to be effective. The herbicide will even work on dormant plants. Furthermore, the herbicidal effect is not dependent on weather conditions, or adversely affected by moisture. Rain or irrigation after application of the herbicidal composition to unwanted plant growth does not destroy the herbicidal effect.

Most terpene compounds, terpene derivatives and essential oils have the advantage of being considerably safer than common agricultural chemicals, such as conventional herbicides. Terpene compounds and derivatives have been widely used, for some years, in medicines, cosmetics and foodstuffs, and thus their safety has been established. Accordingly, the terpene compounds, terpene derivatives and essential oils will also be non-environmentally-polluting and non-toxic to domestic animals. In particular, the herbicides of the present invention are non-residual, when purified pine oil or citrus terpenes are used as the active ingredient.

In use, the terpene, terpene derivative or essential oil may be applied to unwanted plant growth either by itself, or in the form of a conventional herbicidal composition. For example, the active ingredient of the present invention may be mixed with a carrier or diluent to form an easily applied formulation, which may be diluted according to the particular application.

Examples of herbicidal formulations include sprays, liquids, wettable powders, oily solutions, emulsions, dusts, granules, fumigants etc. Application may be by spraying or by means of a "touch" applicator, using a wick assembly.

In particular, emulsions comprising water, an essential oil and a commercial food grade emulsifying agent have been trialled. Whilst the amount of active ingredient is lower in such systems, trials conducted with limonene suggest that volatility is lowered, thereby prolonging contact between the weed and the herbicide. This effect offsets the reduction in active ingredient content.

Alternatively, terpenes, terpene derivatives or essential oils may be blended with other, cheaper, and somewhat less volatile oils to form effective herbicides. For example, various natural oils (such as cottonseed oil, soybean oil, rapeseed oil, sunflower oil, safflower oil, olive oil, coconut oil, coconut milk, corn oil, grape seed oil and peanut oil) have been tested, and found to lack significant herbicidal activity. Nevertheless, they can be blended with the herbicidally-effective essential oils of the present invention to form effective herbicidal compositions.

Because of their environmentally friendly nature and low toxicity, the herbicidal compositions of the present invention will be of particular benefit to the home gardener. However, they may also be used in large-scale agriculture.

In a preferred embodiment, the active ingredient is d-limonene derived from a citrus oil, e.g. orange oil. The fraction comprising d-limonene is separated off by vacuum distillation, or any other conventional separation process. d-Limonene is volatile, and is separated off in the distillate. The distillate is a highly concentrated composition of the terpene compound, comprising about 95-96% by weight of d-limonene and about 4-5% by weight of other components . This distillate may be utilised directly as the herbicidal composition of the present invention.

It should be noted that, although d-limonene is believed to be the active ingredient of this herbicidal composition, other components present in the distillate may also have a herbicidal effect. Furthermore, it may be possible to use unrefined citrus oil, instead of the vacuum distillate. However, vacuum distillation (or other separation process, such as steam distillation (azeotroping), solvent extraction, supercritical extraction etc.) has the advantage of separating the herbicidally active ingredient from flavour components of the citrus oil. The flavour components then form a valuable by-product, which can be utilised in e.g. foodstuffs or pharmaceutical compositions.

The invention will now be further described with respect to the following Examples, which are illustrative but not restrictive of the present invention.

EXAMPLE 1

d-Limonene, which can occur at levels of up to 95% in citrus oils, was distilled from Australian orange oil by vacuum distillation.

The d-limonene used in this trial was approximately 96% pure but, as with all commercially prepared citrus terpenes, contained various other natural compounds distilled in the "cut". The main ones were:

Ethanol alpha-Pinene

Sabinene

Myrcene

Octanal gamma-Terpinene

Linalool

Citronellal alpha-Terpinene

Decanal

Nerol

Neral

Geraniol

Geranial

Dodecanol

Dodecanal.

The d-limonene fraction was applied to vegetation as a fine droplet spray. Knockdown trials were carried out on vegetation growing in heavier (more clay) soils and lighter (more sand) soils. No significant differences in timing or effect were noted.

Knockdown trials were also carried out during different seasons and at different growth stages of the vegetation. Again, no significant differences in timing or effect were noted.

The d-limonene fraction was found to be non-selective and effective against most common vegetation types, including annual and perennial weeds (see Table 1 below). Most vegetation showed visible signs of stress (e.g. wilting or browning) within 2 to 24 hours of application of the herbicide.

Further trials were carried out, as described in Examples 2 to 4 below. The results of these trials are shown in Table 1.

EXAMPLE 2

d-Limonene, which was prepared by the distillation process of Example 1, was formulated as an emulsified mixture of 60% d- limonene with water and commercial emulsifier. Its herbicidal efficacy was tested, using the procedures described in Example 1.

EXAMPLE 3

Similar tests were carried out with dipentene (d,1-limonene) derived from pine oil (a commercial sample, used "neat") .

EXAMPLE 4

A commercial sample of pine oil, used "neat", was tested. TABLE 1

HERBICIDE KNOCKDOWN TRIALS

VEGETATION 96% d-LIMONENE 60% d-LIMONENE DIPENTENE PINE OIL EMULSION (d.l-UMQNENE)

Λ B C -B_ _B.

Soursob

(Oxalis pes-caprae) 12 NO lθ NO 1 12 NO 1 12 NO

Caltrop

(Tribulua terrestris) 12 NO 18 NO 2 12 NO 2 12 NO

Ryegrass (Lolium rigidum) 12 NO 18 NO 2 12 NO 1 6 NO

C

Saffron Thistle (Carthamus lanatυs) 24 24 48 NO 18 48 NO

Wild Turnip - Young Plant 12 12 24 NO 12 18 NO (Braβsica tournefortii)

- Mature Plant 18 18 36 OCCAS 12 36 OCCAS

Couch Grass (Cyno'don dactylon)

Figure imgf000010_0001
6 48 OCCAS 6 36 OCCAS

NOTES : A = Time to first visible streββ (Hrs)

B » Plant knockdown (Hrs) C = Regrowth (after 2 weeks) OCCAS. = Occasional Household style trigger βpray (Calmar Model TS-ΘOO-1) with 500ml reservoir - spray nozzle setting (mist), liuL&J. Aim to achieve 60-00% coverage of vegetation. Solli. Sandy Loam .

EXAMPLE 5

A pine-based emulsion (approx. 30% v/v pine oil in water, with a commercial emulsifying agent) was trialled for herbicidal activity.

The pine-based emulsion was shaken well and test sprayed on 19/07/95 between 9-10am with the temperature below 12°C. The viscosity of this formulation did not allow it to spray well, resulting in only partial coverage. Spray drift was low. Within 8 hours most sprayed plants showed contact necrosis. Where reasonable coverage had been achieved, good kill rates followed. For wild oats and milk thistle, partial coverage allowed recovery by tillering or tip growth respectively. Woody Eucalyptus stem tissue also resprouted.

Results after 10 days were as follows:

Grass, wild oats - rapid dessication of fine leaves but larger leaves more resilient. Growth continued from protected apex.

Gazania - reasonable kill rate with long- lasting effect.

Sour sob - rapid above ground foliar kill, effect on bulb unknown.

Blackwood Wattle - rapid necrosis and permanent kill of foliage and stem to 5mm diameter.

Casuarina - no initial effect; surface dull at 10 days; dead in contact area after 1 month. Saltbush, Rhagodia - rapid necrosis of foliage and stem tissue with permanent kill.

Melaleuca stypheloides - rapid necrosis and permanent kill of foliage and stems <5mm diameter.

Wireweed - rapid necrosis of foliage and stem tissue with permanent kill.

River red gum- rapid necrosis of mature and young foliage, but stems later resprouted. Eucalyptus stem tissue of 5mm diameter and larger resprouted after 2 months.

Other test plants which showed a rapid spray contact kill rate were: Nigella, Plantago, Senecio, Salvation Jane, Medic and Osteospermum. Young Valerian plants died, but older plants with succulent roots only suffered contact damage to foliage. Thistles showed contact damage, but growing tips were not damaged enough to kill the plants. Their growing tips continued to shoot and flower.

Accordingly, the pine-based emulsion was herbicidally effective against numerous species of weeds, some with known glyphosate resistance and some being of a "woody" nature.

While the present invention has been described in terms of preferred embodiments in order to facilitate better understanding of the invention, it should be appreciated that various modifications can be made without departing from the principles of the invention. Therefore, the invention should be understood to include all such modifications within its scope.

Claims

The claims defining the invention are as follows:
1. A herbicidal composition having, as an active
ingredient, a terpene compound, a terpene derivative, or an essential oil comprising a terpene compound or terpene derivative.
2. A herbicidal composition according to claim 1, wherein the active ingredient is a pine oil, a pine alcohol or a terpene compound or derivative derived from pine oil.
3. A herbicidal composition according to claim 1, wherein the active ingredient is a citrus oil, a terpene compound or derivative derived from a citrus oil, tea tree oil (Oil of Melaleuca) or eucalyptus oil.
4. A herbicidal composition according to claim 3, wherein the citrus oil is orange oil, lemon oil, grapefruit oil, mandarin oil, tangerine oil or tangelo oil.
5. A herbicidal composition according to claim 1, wherein the active ingredient is limonene, d-limonene, 1-limonene, d,l-limonene, dipentene, pinene, terpineol, terpinen-4-ol or cineole (eucalyptol).
6. A method for controlling unwanted plant growth, wherein a terpene compound, a terpene derivative, an essential oil comprising a terpene compound or terpene derivative, or a herbicidal composition having, as an active ingredient, a terpene compound, a terpene derivative or an essential oil comprising a terpene compound or terpene derivative is applied to the unwanted plant or plants.
7. A method according to claim 6, wherein the terpene compound, terpene derivative or essential oil is a pine oil, a pine alcohol or a terpene compound or derivative derived from pine oil.
8. A method according to claim 6, wherein the terpene compound, terpene derivative or essential oil is a citrus oil, a terpene compound or derivative derived from a citrus oil, tea tree oil (Oil of Melaleuca) or eucalyptus oil.
9. A method according to claim 8, wherein the citrus oil is orange oil, lemon oil, grapefruit oil, mandarin oil,
tangerine oil or tangelo oil.
10. A method according to claim 6, wherein the terpene compound or terpene derivative is limonene, d-limonene, l-limonene, d,l-limonene, dipentene, pinene, terpineol, terpinen-4-ol or cineole (eucalyptol).
PCT/AU1995/000739 1994-05-11 1995-11-06 Herbicidal composition and method WO1997016975A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AUPM5529A AUPM552994A0 (en) 1994-05-11 1994-05-11 Herbicidal composition
AU17959/95A AU699468B2 (en) 1994-05-11 1995-05-10 Herbicidal composition and method
PCT/AU1995/000739 WO1997016975A1 (en) 1994-05-11 1995-11-06 Herbicidal composition and method

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
AUPM5529A AUPM552994A0 (en) 1994-05-11 1994-05-11 Herbicidal composition
US09/068,355 US5998335A (en) 1995-11-06 1995-11-06 Herbicidal composition and method
AU37680/95A AU3768095A (en) 1995-11-06 1995-11-06 Herbicidal composition and method
PCT/AU1995/000739 WO1997016975A1 (en) 1994-05-11 1995-11-06 Herbicidal composition and method

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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999046994A1 (en) * 1998-03-17 1999-09-23 Barrier Biotech Limited A herbicide
WO1999053764A2 (en) * 1998-04-21 1999-10-28 Organic Interceptor Products Limited Improvements in herbicides
WO2000051436A1 (en) * 1999-03-05 2000-09-08 Ecosmart Technologies, Inc. Herbicidal compositions containing plant essential oils and mixtures or blends thereof
FR2802056A1 (en) * 1999-12-13 2001-06-15 Calliope Sa A herbicidal composition comprising an allelopathic substance and method of use
WO2006052228A1 (en) 2004-11-08 2006-05-18 Oro-Agri, Inc. An adjuvant composition for use with herbicides, pesticides, insecticides, ovicides and fungicides and method of application
WO2006094126A2 (en) 2005-03-02 2006-09-08 Cutting Edge Formulations, Inc. Limonene-containing herbicide compositions, herbicide concentrate formulations and methods for making and using same
US8092817B2 (en) 2001-08-20 2012-01-10 Oro Agri, Inc. Biorational insecticide and fungicide and method of application
US8236336B2 (en) 2001-12-31 2012-08-07 Oro Agri, Inc. Adjuvant composition for use with herbicides, pesticides, insecticides, ovicides and fungicides and method of application
JP5086425B2 (en) * 2008-03-25 2012-11-28 株式会社エス・ディー・エス バイオテック Herbicidal composition and herbicidal method
WO2013124583A1 (en) * 2012-02-23 2013-08-29 Osmobio Total weed control of non-agricultural areas
FR2987231A1 (en) * 2012-02-23 2013-08-30 Osmobio Concentrated emulsion, useful for the eradication of mosses and lichens in cementing surface, comprises aqueous infusion of natural henna plant, nonionic surfactant, and terpenic oxide, monoterpene and sesquiterpene
US8629086B2 (en) 2007-02-06 2014-01-14 Oro Agri, Inc. Compositions and methods for the control of nematodes and soil borne diseases
US9585383B2 (en) 2010-08-20 2017-03-07 Oro Agri, Inc. Methods of reducing phytotoxicity of a pesticide
WO2018055423A1 (en) * 2016-09-21 2018-03-29 Gyógynövénykutató Kft Plant-based plant conditioner and protection product, method of producting such product and use of such product
US10045542B2 (en) 2007-02-06 2018-08-14 Oro Agri, Inc. Citrus oil compositions and methods of use

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE504333C (en) * 1925-06-04 1930-08-02 Schering Kahlbaum Ag Means of combating animal plants Saddle Edlingen
US2512044A (en) * 1947-08-02 1950-06-20 Standard Oil Dev Co Method of selectively eradicating weeds from carrot plots
US3592910A (en) * 1968-10-30 1971-07-13 Arthur R Clark Compositions and method for controlling release of pesticides using terpene polymers
US4587123A (en) * 1984-06-28 1986-05-06 Price Jacqueline S Compositions and methods for reducing pest infestation
GB2188931A (en) * 1986-04-14 1987-10-14 Shell Int Research Halogenated heterocyclic ether herbicides
WO1988002598A1 (en) * 1986-10-10 1988-04-21 E.I. Du Pont De Nemours And Company Herbicidal mixtures
AU1951788A (en) * 1988-03-17 1989-10-05 Institut Fiziko-Organicheskoi Khimii Akademii Nauk Belorusskoi SSR Method of sterilizing plant anthers utilizing derivatives of terpenoid
EP0388164A1 (en) * 1989-03-14 1990-09-19 E.I. Du Pont De Nemours And Company Selective oxabicycloalkanes
WO1993019598A1 (en) * 1992-04-06 1993-10-14 Robert Vincent Thompson Improvements in the herbicidal treatment of plants
US5407899A (en) * 1992-10-09 1995-04-18 Applied Biochemists Inc. Algaecidal and herbicidal compositions comprising terpene wetting agents
AU1388295A (en) * 1993-12-24 1995-07-17 Action Pin Use of at least one terpenic carbide and/or a derivative thereof as an additive to a herbicide slurry or coformulant of a herbicide composition
AU1795995A (en) * 1994-05-11 1995-11-16 Certified Organics Limited Herbicidal composition and method

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE504333C (en) * 1925-06-04 1930-08-02 Schering Kahlbaum Ag Means of combating animal plants Saddle Edlingen
US2512044A (en) * 1947-08-02 1950-06-20 Standard Oil Dev Co Method of selectively eradicating weeds from carrot plots
US3592910A (en) * 1968-10-30 1971-07-13 Arthur R Clark Compositions and method for controlling release of pesticides using terpene polymers
US4587123A (en) * 1984-06-28 1986-05-06 Price Jacqueline S Compositions and methods for reducing pest infestation
GB2188931A (en) * 1986-04-14 1987-10-14 Shell Int Research Halogenated heterocyclic ether herbicides
WO1988002598A1 (en) * 1986-10-10 1988-04-21 E.I. Du Pont De Nemours And Company Herbicidal mixtures
AU1951788A (en) * 1988-03-17 1989-10-05 Institut Fiziko-Organicheskoi Khimii Akademii Nauk Belorusskoi SSR Method of sterilizing plant anthers utilizing derivatives of terpenoid
EP0388164A1 (en) * 1989-03-14 1990-09-19 E.I. Du Pont De Nemours And Company Selective oxabicycloalkanes
WO1993019598A1 (en) * 1992-04-06 1993-10-14 Robert Vincent Thompson Improvements in the herbicidal treatment of plants
US5407899A (en) * 1992-10-09 1995-04-18 Applied Biochemists Inc. Algaecidal and herbicidal compositions comprising terpene wetting agents
AU1388295A (en) * 1993-12-24 1995-07-17 Action Pin Use of at least one terpenic carbide and/or a derivative thereof as an additive to a herbicide slurry or coformulant of a herbicide composition
AU1795995A (en) * 1994-05-11 1995-11-16 Certified Organics Limited Herbicidal composition and method

Non-Patent Citations (21)

* Cited by examiner, † Cited by third party
Title
BIOLOGICALLY ACTIVE NATURAL PRODUCTS: POTENTIAL USE IN ARGRICULTURE, AMERICAL CHEMICAL SOCIETY SYMPOSIUM SERIES (1988), H.G. CURLER Editor, Washington, D.C., Chapter 16, "Terpenoids as Models for New Agrochemicals", by S.D. ELAKOVICH, pages 250-261. *
BULLETIN OF THE TORREY BOTANICAL CLUB, 1964, 91(4), pages 237-330, W.H. MULLER and C.H. MULLER, "Volatile Growth Inhibitors Produced by Salvia Species". *
CHEMICAL AND ENGINEERING NEWS, (1983), 61(14), April 4, A.R. PUTNAM, "Allelopathic Chemicals, Nature's Herbicides in Action", pages 34-45. *
DERWENT ABSTRACT, Accession No. 87-286557; & GB,A,2 188 931 (SHELL INT. RES. MIY BV), Class C02, 14 October 1987. *
DERWENT ABSTRACT, Accession No. 88-119336, Class C02; & WO,A,88 02598 (DU PONT DE NEMOURS CO.) 21 April 1988. *
DERWENT ABSTRACT, Accession No. 88-216573, Class C02 (C03); & JP,A,63 152 303, (MITSUBISHI PETROCH KK), 24 June 1988. *
DERWENT ABSTRACT, Accession No. 88-231637, Class C02 (C03); & JP,A,63 165 301, (SHELL KAGAKU KK), 8 July 1988. *
DERWENT ABSTRACT, Accession No. 90-284353, Class C02; & EP,A,388 164, (DU PONT DE NEMOURS CO.), 19 September 1990. *
DERWENT ABSTRACT, Accession No. 91-152274, Class C03; & JP,A,03 086 802 (SANYO CHEM. IND. LTD.), 11 April 1991. *
DERWENT ABSTRACT, Accession No. 93-299519, Class C03; & JP,A,05 213 711 (SOLAR JAPAN KK), 24 August 1993. *
ENVIRON. ENTOMOL., (1986), 15(6), pages 1192-1198, K.H. HAAG, "Effects of Herbicide Application on Mortality and Dispersive Behaviour of the Water Hyacinth Weevils, Neochetina Eichlorniae and Neochetina Bruchi (Coleoptera: Curculionidae)", page 1194. *
JOURNAL OF CHEMICAL ECOLOGY, (1989), 15(5), G.B. WILLIAMSON et al., "Chemical Inhibition of Fire - Prone Grasses by Fire - Sensitive Shrub. Conradina Canescens", pages 1567-1577. *
JOURNAL OF CHEMICAL ECOLOGY, 1985, 11(11), pages 1527-1534, I.S. ALSAADAWI et al., "Allelopathatic Effects of Citrus Aurantium L.II. Isolation, Characterisation, an Biological Activities of Phytotoxins". *
KIRK-OTHMER, ENCYCLOPEDIA OF CHEMICAL TECHNOLOGY, Third Edition, Volume 22, JOHN WILEY AND SONS, NEW YORK, pages 709-712. *
PROC. BR. CROP. CONF., 1985, Vol. 12, pages 265-270, J.W. MAY et al., "SD 95481 a Versatile New Herbicide with Wide Spectrum Crop Use". *
PROC. MONTANA ACAD. SCI., (1982), 41, T. WEAVER and L. KISH, "Allelopathic Potential of Terpene Secreting (Aromatic) Plants", pages 51-56. *
THE AMER. MIDLAND NATURALIST, 1970, Vol. 83, R. DEL MORAL and C.H. MULLER, "The Allelopathic Effects of Eucalyptus Camaldulensis", pages 262-266. *
THE MERK INDEX, Tenth Edition, MERCK AND CO., INC. RAHWAY, N.J. USA, Monographs 3840, 5321, 6658, 6668, 6692, 7319, 7320, 7321. *
THE SCIENCE OF ALLELOPATHY, JOHN WILEY AND SONS, NEW YORK, (1986), Chapter 12, (pages 203-218), N.H. FISCHER, "The Function of Mono and Sesquiterpenes as Plant Germination and Growth Regulators". *
WEED CONTROL AS A SCIENCE, G.C. KLINGMAN, JOHN WILEY AND SONS, INC., USA, September 1963, Chapter 14, "Other Organic Herbicides", pages 208-225. *
WEED SCIENCE, (1993), 41(1), S.F. VAUGHN and G.F. SPENCER, "Volatile Monoterpenes as Potential Parent Structures for New Herbicides", pages 114-119. *

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