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WO2025172301A1 - Method of crop enhancement - Google Patents

Method of crop enhancement

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Publication number
WO2025172301A1
WO2025172301A1 PCT/EP2025/053602 EP2025053602W WO2025172301A1 WO 2025172301 A1 WO2025172301 A1 WO 2025172301A1 EP 2025053602 W EP2025053602 W EP 2025053602W WO 2025172301 A1 WO2025172301 A1 WO 2025172301A1
Authority
WO
WIPO (PCT)
Prior art keywords
spiropidion
plant
active ingredient
pistachio
budding
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
PCT/EP2025/053602
Other languages
French (fr)
Inventor
Robert Senn
Mehdi MOHSENNASAB
Babak KESHAVARZ
Zaid NABAS
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Syngenta Crop Protection AG Switzerland
Original Assignee
Syngenta Crop Protection AG Switzerland
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 Syngenta Crop Protection AG Switzerland filed Critical Syngenta Crop Protection AG Switzerland
Publication of WO2025172301A1 publication Critical patent/WO2025172301A1/en
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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 OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof

Definitions

  • the present invention relates to the use of the ketoenol insecticide spiriopidion for crop enhancement effects in pistachio (Pistacia vera) plants.
  • pistachio Plantacia vera
  • Pistachio (Pistacia vera), native to regions of central Asia, belongs to the Anacardiaceae family of flowering plants and is now important as an agricultural crop cultivated throughout the world for its seeds that are widely consumed as food for humans, for example, as pistachio nuts or for the pistachio flavouring of cakes, pastries, ice cream, etc.
  • Spiropidion (CAS no.: 1229023-00-0. 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2- oxo-1 ,8-diazaspiro[4.5]dec-3-en-4-yl ethyl carbonate) is known from, eg, WO 2010/066780, WO 2018/114648, WO 2018/114649 and WO 2022/194582, and is effective in the control of pests, including sucking insects such as aphids, white flies, scales and mites.
  • Spiropidion may be used as part of a pesticidal treatment program for controlling the various insect pests which may be problematic for the production of pistachio nuts.
  • pistachio psyllid Algonoscena pistaciae
  • pistachio leaf hopper Idiocerus stali
  • pistachio twig and fruit scale Pistaciaspis pistaciae
  • pistachio trunk and branch scale Melanaspis inopinata
  • pistachio mealybug Ferrisia gilli
  • pistachio eriophyid mites Aceria pistaciae and Aceria stephanii
  • pistachio common mite Triggerpus granati
  • a method of increasing budding in a pistachio plant comprising applying spiropidion to the plant, plant part or to the locus thereof.
  • spiropidion for increasing budding in a pistachio plant.
  • Budding may be defined as a compact growth on a plant (eg, a stem, branch or a trunk) that develops into a leaf, flower, or shoot.
  • a plant eg, a stem, branch or a trunk
  • the terms “tree” and “plant” should be considered as interchangeable.
  • the application of spiropidion described in accordance with the present invention relates to the enhancement of the overall health, strength and viability of the plant buds to improve their capacity to survive winter conditions and emerge as viable in the spring (ie, the “vitality” of the buds). This may lead to better overall plant health, increased flowering and potentially higher nut yields in the subsequent growing season.
  • a spiropidion-containing composition used in accordance with the present invention may be applied containing the various adjuvants and carriers known to or used in the industry.
  • Preferred as formulation types for dilution of the pesticidal active ingredient (ai) in a spray tank include a suspension concentrate (SC) or a wettable granule (WG).
  • SC suspension concentrate
  • WG wettable granule
  • the dilutions can be made, for example, with water, liquid fertilisers, micronutrients, biological organisms, oil or solvents.
  • Spiropidion-containing compositions used according to the present invention may be prepared according to known formulation methods, eg, as a suspension concentrate formulation.
  • the concentration of spiropidion in a composition for the use or method according to the invention may be from 3 to 8 grams of spiropidion per 100 L, preferably 4 to 8 grams of spiropidion per 100 L, and more preferably 5 to 8 grams of spiropidion per 100 L.
  • Typical treatment rates of application per plant may be 1 to 6 mg of spiropidion, and preferably 1 to 4 mg of spiropidion per plant. The rates of application may vary and depend on the method of application, the plant, the pest to be controlled, the prevailing climatic conditions, other factors governed by the method of application, and the time of application.
  • Single doses may be in the range of 100 to 300 g ai (spiropidion)Zha, 100 to 240 g ai/ha, or 100 to 225 g ai/ha, which may be applied as a single or multiple applications at an appropriate interval.
  • Spiropidion may be applied as the sole insecticidal active ingredient, or else the application may further comprise treatment with an additional pesticidal active ingredient selected from: chlorpyrifos, acetamiprid, diazinon, phosmet, abamectin, bifenthrin, permethrin, imidacloprid, thiamethoxam, lamda-cyhalothrin, spinetoram, fenpropathrin, fenoxycarb, fenthion, fenitrothion, ethion, thiacloprid, sulfur, isocycloseram.
  • an additional pesticidal active ingredient selected from: chlorpyrifos, acetamiprid, diazinon, phosmet, abamectin, bifenthrin, permethrin, imidacloprid, thiamethoxam, lamda-cyhalothrin, spinetoram,
  • the ratio (by weight) of spiropidion to the additional pesticidal active ingredient may be from 50:1 to 1 :50, 20:1 to 1 :20, 10:1 to 1 :10, 5:1 to 1 :5, 2:1 to 1 :2, or indeed in a ratio of 1 :1 .
  • the active ingredients may be applied in the same treatment or as separate treatments.
  • the adjuvant is selected from a mineral oil, a vegetable oil, an esterified vegetable oil, a methylated vegetable oil or an alkyl ester phosphate-based adjuvant.
  • a pesticide adjuvant may be defined as a substance present in a pesticidal composition (eg, a concentrated active ingredient formulation diluted in water in a tank for a foliar spray application on a crop), which improves pesticidal active ingredient performance, for example by facilitating the spreading of the active ingredient on a leaf surface or penetration into the leaf of the crop plant.
  • adjuvant classes which may be used in accordance with the present invention include a mineral oil, a vegetable oil, an esterified vegetable oil, a methylated vegetable oil or an alkyl ester phosphate-based adjuvant.
  • Commercially-available adjuvant products which may be tank-mixed to yield a spray fomulation with the composition of the present invention include HASTENTM (Victorian Chemical Co. Pty. Ltd.
  • the alkyl ester phosphate of the adjuvant is preferably tris- (2-ethylhexyl) phosphate, preferably in combination with ethoxylated sorbitol, hexaoleate, eg, OCHIMA® - EC, Syngenta.
  • Table 2 relates to the number of live buds taken from trees with spiropidion treatment, spirotetramat treatment and the standard farmer’s practice (FP) treatment (without spiropidion and spirotetramat treatment) comprising an application of chlorpyrifos (from 40.8% EC formulation) at 100 mL of active ingredient per hectolitre.
  • FP standard farmer’s practice
  • Active ingredients applied as tank-mix dilutions as follows (g ai/ha grams of active ingredient/hectare): - Spiropidion from ELESTAL® 300 SC (Syngenta Crop Protection AG) at a rate of 150 g ai/ha.
  • Spiropidion and spirotetramat spray treatments comprised mineral oil (80% paraffin) as the adjuvant.
  • the adjuvant itself does not confer effects on budding, but rather acts as a facilitator for penetration into plant tissues.

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

A method of increasing budding in a pistachio plant (Pistacia vera), the method comprising applying spiropidion active ingredient to the plant, plant part, or to the locus thereof.

Description

METHOD OF CROP ENHANCEMENT
The present invention relates to the use of the ketoenol insecticide spiriopidion for crop enhancement effects in pistachio (Pistacia vera) plants. In particular, to a method of increasing budding in a pistachio plant using spiropidion.
Pistachio (Pistacia vera), native to regions of central Asia, belongs to the Anacardiaceae family of flowering plants and is now important as an agricultural crop cultivated throughout the world for its seeds that are widely consumed as food for humans, for example, as pistachio nuts or for the pistachio flavouring of cakes, pastries, ice cream, etc.
Spiropidion (CAS no.: 1229023-00-0. 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2- oxo-1 ,8-diazaspiro[4.5]dec-3-en-4-yl ethyl carbonate) is known from, eg, WO 2010/066780, WO 2018/114648, WO 2018/114649 and WO 2022/194582, and is effective in the control of pests, including sucking insects such as aphids, white flies, scales and mites.
Spiropidion may be used as part of a pesticidal treatment program for controlling the various insect pests which may be problematic for the production of pistachio nuts. These include, but are not limited to, pistachio psyllid (Agonoscena pistaciae), pistachio leaf hopper (Idiocerus stali), pistachio twig and fruit scale (Pistaciaspis pistaciae), pistachio trunk and branch scale (Melanaspis inopinata), pistachio mealybug (Ferrisia gilli), pistachio eriophyid mites (Aceria pistaciae and Aceria stephanii) and pistachio common mite (Tenuipalpus granati).
It has been unexpectedly found that the application of spiropidion to pistachio plants may, as well as provide insecticidal activity, significantly increase budding on the stems and branches of the plant, thereby leading to greater flowering and seed production, and thus yield of commercially valuable pistachio nuts.
According to the present invention, there is provided a method of increasing budding in a pistachio plant (Pistacia vera), the method comprising applying spiropidion to the plant, plant part or to the locus thereof.
Further according to the present invention, there is provided the use of spiropidion for increasing budding in a pistachio plant.
Budding may be defined as a compact growth on a plant (eg, a stem, branch or a trunk) that develops into a leaf, flower, or shoot. In the context of the present invention, the terms “tree” and “plant” should be considered as interchangeable.
In the context of increasing the budding on a pistachio plant, the application of spiropidion described in accordance with the present invention relates to the enhancement of the overall health, strength and viability of the plant buds to improve their capacity to survive winter conditions and emerge as viable in the spring (ie, the “vitality” of the buds). This may lead to better overall plant health, increased flowering and potentially higher nut yields in the subsequent growing season.
In practice, a spiropidion-containing composition used in accordance with the present invention may be applied containing the various adjuvants and carriers known to or used in the industry. Preferred as formulation types for dilution of the pesticidal active ingredient (ai) in a spray tank include a suspension concentrate (SC) or a wettable granule (WG). The dilutions can be made, for example, with water, liquid fertilisers, micronutrients, biological organisms, oil or solvents. Spiropidion-containing compositions used according to the present invention may be prepared according to known formulation methods, eg, as a suspension concentrate formulation.
The concentration of spiropidion in a composition for the use or method according to the invention may be from 3 to 8 grams of spiropidion per 100 L, preferably 4 to 8 grams of spiropidion per 100 L, and more preferably 5 to 8 grams of spiropidion per 100 L. Typical treatment rates of application per plant may be 1 to 6 mg of spiropidion, and preferably 1 to 4 mg of spiropidion per plant. The rates of application may vary and depend on the method of application, the plant, the pest to be controlled, the prevailing climatic conditions, other factors governed by the method of application, and the time of application. Single doses may be in the range of 100 to 300 g ai (spiropidion)Zha, 100 to 240 g ai/ha, or 100 to 225 g ai/ha, which may be applied as a single or multiple applications at an appropriate interval.
Spiropidion may be applied as the sole insecticidal active ingredient, or else the application may further comprise treatment with an additional pesticidal active ingredient selected from: chlorpyrifos, acetamiprid, diazinon, phosmet, abamectin, bifenthrin, permethrin, imidacloprid, thiamethoxam, lamda-cyhalothrin, spinetoram, fenpropathrin, fenoxycarb, fenthion, fenitrothion, ethion, thiacloprid, sulfur, isocycloseram.
The ratio (by weight) of spiropidion to the additional pesticidal active ingredient may be from 50:1 to 1 :50, 20:1 to 1 :20, 10:1 to 1 :10, 5:1 to 1 :5, 2:1 to 1 :2, or indeed in a ratio of 1 :1 . The active ingredients may be applied in the same treatment or as separate treatments.
Preferably, in an aqueous composition according to the invention (eg, a tank mix preparation for applying to a crop), the adjuvant is selected from a mineral oil, a vegetable oil, an esterified vegetable oil, a methylated vegetable oil or an alkyl ester phosphate-based adjuvant. A pesticide adjuvant may be defined as a substance present in a pesticidal composition (eg, a concentrated active ingredient formulation diluted in water in a tank for a foliar spray application on a crop), which improves pesticidal active ingredient performance, for example by facilitating the spreading of the active ingredient on a leaf surface or penetration into the leaf of the crop plant.
Examples of adjuvant classes, which may be used in accordance with the present invention include a mineral oil, a vegetable oil, an esterified vegetable oil, a methylated vegetable oil or an alkyl ester phosphate-based adjuvant. Commercially-available adjuvant products which may be tank-mixed to yield a spray fomulation with the composition of the present invention include HASTEN™ (Victorian Chemical Co. Pty. Ltd. - blend of an esterified vegetable oil and non-ionic surfactants), OCHIMA® (Syngenta - alkyl ester of phosphoric acid (EC formulation)), LEDNA™ (Polaquimia - EC formulation comprising a methyl ester of soybean oil), Atplus® 463 (CRODA Europe Limited - 60% parafin oil with surfactant blend), Actirob® B (Bayer AG - rapeseed oil methyl ester (esterified vegetable oil)), Destiny® HC (Winfield Solutions LLC - methylated soybean oil), DYNE-AMIC® (HELENA - blend of (methylated) vegetable oil and organosilicon-based nonionic surfactants), and FS Optique™ (GROWMARK, Inc - methyl ester of canola oil).
If an alkyl ester phosphate-based adjuvant is used in conjunction with the pesticidal composition according to the invention (ie, in a tank mix), the alkyl ester phosphate of the adjuvant is preferably tris- (2-ethylhexyl) phosphate, preferably in combination with ethoxylated sorbitol, hexaoleate, eg, OCHIMA® - EC, Syngenta.
EXAMPLES:
Methods
Mature pistachio trees at eight different growing locations in Iran (Locations 1 to 8) were given an initial spray treatment with spiropidion or spirotetramat active ingredients according to the details given below in Table 1. The initial spray treatments took place in June at BBCH 69 to BBCH 79. With the exception of Location 8, a subsequent treatment was applied at 14 to 41 days after the initial treatment with agricultural soap (Location 1), chlorpyrifos (Locations 2 and 4 to 7) or abamectin (Location 3).
The number of live buds were counted on 30 randomly selected branch shoots taken from the mid-height of the trees 9 months (in March the subsequent year) after initial treatment. Table 2 relates to the number of live buds taken from trees with spiropidion treatment, spirotetramat treatment and the standard farmer’s practice (FP) treatment (without spiropidion and spirotetramat treatment) comprising an application of chlorpyrifos (from 40.8% EC formulation) at 100 mL of active ingredient per hectolitre.
Table 1 :
Active ingredients applied as tank-mix dilutions as follows (g ai/ha = grams of active ingredient/hectare): - Spiropidion from ELESTAL® 300 SC (Syngenta Crop Protection AG) at a rate of 150 g ai/ha.
- Spirotetramat from Navigator 10% SC (Agrobest®) at a rate of 150 - 200 g ai/ha.
- Agricultural soap (100 - 200 mL/hL) from Jonobgan® (35% di-octyl sodium sulfosuccinate) at a rate of 350 to 700 g ai/ha.
- Abamectin (100 mL/hL) from Aria 1.8% EC (Ariashimi) at a rate of 36 g ai/ha. - Chlorpyrifos (150 mL/hL) from Samsachior EC 40.8% (Samsazan) at a rate of 1224 g ai/ha.
Spiropidion and spirotetramat spray treatments comprised mineral oil (80% paraffin) as the adjuvant. The adjuvant itself does not confer effects on budding, but rather acts as a facilitator for penetration into plant tissues.
Table 2:
As can be seen from Table 2, treatments with spiropidion provided a significant increase in the number of live buds observed compared to a standard farmer’s insecticidal treatment (63% more buds) and spirotetramat (48% more buds).
This crop enhancement effect of budding was observed for spirotetramat, but was significantly improved with the use of spiropidion.
In general terms, 30% of buds on pistachio plants are utilized by the plant for shooting in the subsequent season, whereas the remaining 70% of buds will develop into flowering clusters during the present season, which subsequently bear nuts for harvest. The data in Table 2 show on average an approximately 40% greater fruit (nut) yield with the spiropidion treatment expected against the spirotetramat treatment, when the farming practice continued in an optimum condition during the subsequent growing season.

Claims

Claims:
1. A method of increasing budding in a pistachio plant (Pistacia vera), the method comprising applying spiropidion active ingredient to the plant, a plant part or to the locus thereof.
2. The method according to claim 1 , wherein the spiropidion is applied as an aqueous dilution of a suspension concentrate (SC) formulation.
3. The method according to claim 2, wherein the formulation comprises spiropidion as the sole pesticidal active ingredient.
4. The method according to any one of claims 1 to 3, wherein the application further comprises treatment with an additional pesticidal active ingredient selected from: chlorpyrifos, acetamiprid, diazinon, phosmet, abamectin, bifenthrin, permethrin, imidacloprid, thiamethoxam, lamda-cyhalothrin, spinetoram, fenpropathrin, fenoxycarb, fenthion, fenitrothion, ethion, thiacloprid, sulfur, isocycloseram.
5. The method according to any one of claims 1 to 4, wherein the application is as one or more spray treatments.
6. The method according to claim 5, wherein the application of spiropidion is as a single spray treatment.
7. The method according to any one of claims 1 to 6, wherein the spiropidion active ingredient is applied at a rate of 100 to 300 g/ha per treatment.
8. The method according to any one of claims 1 to 7, wherein the spiropidion active ingredient is applied at a rate of 150 to 225 g/ha per treatment.
9. The method according to any one of claims 1 to 8, wherein spiropidion is applied as a composition in the presence of an adjuvant selected from a mineral oil, a vegetable oil, an esterified vegetable oil, a methylated vegetable oil or an alkyl ester phosphate-based adjuvant.
10. The method according to claim 9, wherein the adjuvant is a mineral oil.
11 . The method according to any one of claims 1 to 10, wherein the plant part is a leaf.
12. The method according to any one of claims 1 to 11 , wherein increasing budding comprises enhancing the winter survival capability of the buds to preserve bud viability.
13. The method according to claim 12, wherein bud viability provides increased flowering and higher nut yields in a subsequent growing season
14. Use of spiropidion for increasing budding in a pistachio plant.
PCT/EP2025/053602 2024-02-12 2025-02-11 Method of crop enhancement Pending WO2025172301A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP24157056.3 2024-02-12
EP24157056 2024-02-12

Publications (1)

Publication Number Publication Date
WO2025172301A1 true WO2025172301A1 (en) 2025-08-21

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
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Country Status (1)

Country Link
WO (1) WO2025172301A1 (en)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010066780A1 (en) 2008-12-12 2010-06-17 Syngenta Participations Ag Spiroheterocyclic n-oxypiperidines as pesticides
WO2018114649A1 (en) 2016-12-22 2018-06-28 Syngenta Participations Ag Polymorphs
WO2018114648A1 (en) 2016-12-22 2018-06-28 Syngenta Participations Ag Polymorphs
WO2022194582A1 (en) 2021-03-16 2022-09-22 HELLA GmbH & Co. KGaA Light body for a lighting unit of a vehicle, lighting unit of a vehicle, and method for setting the electric current of a light source of a light body

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010066780A1 (en) 2008-12-12 2010-06-17 Syngenta Participations Ag Spiroheterocyclic n-oxypiperidines as pesticides
WO2018114649A1 (en) 2016-12-22 2018-06-28 Syngenta Participations Ag Polymorphs
WO2018114648A1 (en) 2016-12-22 2018-06-28 Syngenta Participations Ag Polymorphs
WO2022194582A1 (en) 2021-03-16 2022-09-22 HELLA GmbH & Co. KGaA Light body for a lighting unit of a vehicle, lighting unit of a vehicle, and method for setting the electric current of a light source of a light body

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
KAMIAB FERESHTEH ET AL: "Application of some bloom thinning techniques to overcome alternate bearing in pistachio (L.)", HORTICULTURE, ENVIRONMENT AND BIOTECHNOLOGY, KOREAN SOCIETY FOR HORTICULTURAL SCIENCE, KOREA, vol. 61, no. 1, 3 December 2019 (2019-12-03), pages 31 - 39, XP037018906, ISSN: 2211-3452, [retrieved on 20191203], DOI: 10.1007/S13580-019-00187-9 *
MAHDAVI VAHIDEH ET AL: "Human health risk assessment of spiropidion and the main metabolites SYN547305 (spiropidion-enol), SYN 547435, and SYN 548430 in pistachio with UHPLC-MS/MS", vol. 121, 1 August 2023 (2023-08-01), AMSTERDAM, NL, pages 105353, XP093180872, ISSN: 0889-1575, Retrieved from the Internet <URL:https://pdf.sciencedirectassets.com/272389/1-s2.0-S0889157523X00052/1-s2.0-S0889157523002272/main.pdf?X-Amz-Security-Token=IQoJb3JpZ2luX2VjELj%2F%2F%2F%2F%2F%2F%2F%2F%2F%2FwEaCXVzLWVhc3QtMSJHMEUCIA9znKpH4H3IKCFATYaeaelJNpVF%2FTE983%2BVycXuC11DAiEA4CAJiKJvYEcZ73I59eYrqH4MDUnGr6KDpZYQNJBIiXoqsgUIcRAFG> DOI: 10.1016/j.jfca.2023.105353 *
RAHEMI ET AL: "Potential of ethephon, NAA, NAD and urea for thinning pistachio fruitlets", SCIENTIA HORTICULTURAE, ELSEVIER, AMSTERDAM, NL, vol. 111, no. 2, 5 December 2006 (2006-12-05), pages 160 - 163, XP005793677, ISSN: 0304-4238, DOI: 10.1016/J.SCIENTA.2006.10.002 *

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