WO2016092467A1 - Nouvelle composition granulaire encapsulée synergique - Google Patents

Nouvelle composition granulaire encapsulée synergique Download PDF

Info

Publication number
WO2016092467A1
WO2016092467A1 PCT/IB2015/059438 IB2015059438W WO2016092467A1 WO 2016092467 A1 WO2016092467 A1 WO 2016092467A1 IB 2015059438 W IB2015059438 W IB 2015059438W WO 2016092467 A1 WO2016092467 A1 WO 2016092467A1
Authority
WO
WIPO (PCT)
Prior art keywords
fipronil
composition
cartap hydrochloride
synergistic
insecticidal
Prior art date
Application number
PCT/IB2015/059438
Other languages
English (en)
Inventor
Parikshit MUNDHRA
Jitendra Mohan
Original Assignee
Willowood Chemicals Private Limited
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 Willowood Chemicals Private Limited filed Critical Willowood Chemicals Private Limited
Publication of WO2016092467A1 publication Critical patent/WO2016092467A1/fr

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
    • A01N47/00—Biocides, 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
    • A01N47/08—Biocides, 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 one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • 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
    • A01N47/00—Biocides, 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
    • A01N47/02—Biocides, 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

Definitions

  • the present invention relates to insecticidal encapsulated granular composition comprising fipronil and cartap hydrochloride, and a method for preparing such composition.
  • Crop protection technology which includes all pesticides, herbicides, insecticides, fungicide, as well as biotechnological products helps control the thousands of weed species, harmful insects and numerous plant diseases that afflict crops.
  • food production would decline, many fruits and vegetables would be in short supply and the price of food would rise.
  • the production of important fibres for clothing such as cotton would decrease as farmers would lose their harvest and livelihoods to crop pests and diseases.
  • crop protection is very important to increase the production of agricultural products and at the same time reduce their cost.
  • insecticidal agents and compositions have been developed to control insect pests such as agro-horticultural pests or hygienic pests and in practice have been used as a single or a mixed agent but economically efficient and ecologically safe insect control compositions are still being sought.
  • Insecticidal compositions which allow for reduced effective dosage rates, increased environmental safety and lower the incidence of insect resistance are highly desirable.
  • the rotational application of insect control agents having different modes of action may be adopted for good pest management practice. However, this does not necessarily give satisfactory insect control.
  • insecticidal combinations offer significant advantages over individual applications including improved and extended insect control, reduced insecticide rates and application costs, shorter contact times for improved results, less stringent use restrictions, improved selectivity, improved spectrum of insect-pest controlled, reduced cost and reduced residue problems.
  • identifying appropriate insecticidal application rates and combinations is essential to achieve synergistic insect control.
  • obtaining an insecticidal combination which demonstrates no cross-resistance to the existing insecticidal agents, no toxicity problems and little negative impact on the environment is extremely difficult.
  • Insecticides with a pyrazole, pyrrole or phenylimidazole group include those described in the applications for European Patents EP 0295117, EP 0460940 or EP 0484165, respectively. Among them is phenyl pyrazole, whose common name is fipronil, and IUPAC name is ( ⁇ )-5-amino-l-(2,6-dichloro-a,a,a-trifluoro-p- tolyl)-4-trifluoromethylsulfinylpyrazole-3-carbonitrile.
  • fipronil Apart from its disclosure in the application EP 0295117, the properties of the compound fipronil have been published in the report of the 1992 Brighton Crop Protection Conference (Pests and Diseases, pages 29-34). The structure of fipronil is as follows:
  • Fipronil is a broad-spectrum phenylpyrazole insecticide used to control ants, beetles, cockroaches, fleas, ticks, termites, mole crickets, thrips, rootworms, weevils and other insects. Fipronil blocks GABAA-gated chloride channels in the central nervous system. Disruption of the GABAA receptors by fipronil prevents the uptake of chloride ions resulting in excess neuronal stimulation and death of the target insect. Insects resistant to pyrethroid, cyclodiene, organophosphorous and/or carbamate insecticides are susceptible to fipronil. Fipronil is broad spectrum insecticide toxic by contact and ingestion.
  • Cartap hydrochloride (IUPAC S,S'-(2-dimethylaminotrimethylene) bis(thiocarbamate) hydrochloride), a derivative of nereistoxin, a naturally occurring insecticidal substance isolated from the marine segmented worms Lumbrinereis heteropoda and Lumbrinereis brevicirra.
  • Cartrap hydrochloride is a highly effective, broad-spectrum, low toxic and low residual insecticide, causing paralysis by cholinergic blocking action on the central nervous system of insect. It is a systemic insecticide with stomach and contact action. Insects discontinue feeding, and die of starvation.
  • the structure of cartap hydrochloride is as follows:
  • Cartap hydrochloride is used against a relatively broad spectrum of insects, e.g., Lepidoptera, Coleoptera, Diptera and Hemiptera. It is especially effective against Lepidoptera such as the rice stem borer, diamond-back moth and common cabbage worm, and Coleoptera such as the Colorado potato beetle, Mexican bean beetle etc. Approximately 70% of the world production of cartap hydrochloride is applied to rice and 30% to other crops, vegetables, potatoes, fruit, tea, etc. Cartap hydrochloride is also used for controlling the rice white-tip nematode by soaking rice seed in an aqueous solution of the insecticide.
  • Cartap hydrochloride is used against a relatively broad spectrum of insects, e.g., Lepidoptera, Coleoptera, Diptera and Hemiptera. It is especially effective against Lepidoptera such as the rice stem borer, diamond-back moth and common cabbage worm, and Coleoptera such as the Colorado potato beetle, Mexican bean beetle etc.
  • the standard composition of cartap hydrochloride available in the art is 50 percent soluble powder and 4 percent granules.
  • disadvantages associated with the use of these For example, disadvantages associated with powder composition and immediate release of active in case of granules resulting in reduced control period.
  • JP 2001081003 discloses a microbial insecticidal composition containing Cartap hydrochloride (as an active ingredient) along with at least one kind of phenyl alkanic acid amide derivative for paddy field.
  • JP 09124406 discloses a granulated water dispersible powder containing cartap hydrochloride, alongwith Acephate, Nitenpyram, Bensultap in combination with zinc oxide, MgO, T1O 2 , AI 2 O 3 .
  • JP 08225404 discloses a stabilized agrochemical preparation of cartap hydrochloride and cyclodextrins.
  • JP 02174702 discloses an active agrochemical composition of cartap hydrochloride mixed with octyldiphenyl phosphate.
  • WO 2012101659 Al discloses an active agrochemical composition of fipronil mixed with sulphur.
  • U.S. Pat. No. 5747519 (A) teaches a termite control composition for soil treatment containing bifenthrin and fipronil, and a method of controlling termites using said composition.
  • the publication does not disclose whether a mixture of bifenthrin and fipronil will be suitable in agricultural pest control.
  • US 2011/0039907 teaches a method of ant control using mixtures of fipronil and a pyrethroid insecticide such as bifenthrin particularly in yards, gardens, parks, lawns and golf courses.
  • compositions that offer a broad spectrum of protection, addresses the concerns of resistance, improves foliage, improves handling, improves rainfastedness and in various instances, improves crop yield and grain quality.
  • the compositions can be applied as a foliar spray or to the soil, through broadcasting or through drip or trickle irrigation. The latter case of drip or trickle irrigation further optimizes farming practices, which are greatly challenged by an ever-increasing labour and water shortage.
  • drip or trickle irrigation further optimizes farming practices, which are greatly challenged by an ever-increasing labour and water shortage.
  • the compositions at very low concentrations of the active ingredients can be effectively applied, thereby reducing the burden on the environment.
  • the compositions at lower rates of the active ingredients in combination together provided a longer duration of control of the pest and avoided pest outbreak and resurgence.
  • CG encapsulated granular
  • an insecticidal composition comprising fipronil and cartap hydrochloride in a synergistic ratio of 1 : 15-1 :8 for efficacious insect control.
  • fipronil may be present in an amount in the range from 0.1 to 10% w/w.
  • cartap hydrochloride may be present in the range from 1.0 to 25% w/w.
  • the synergistic insecticidal combination may be formulated as dust, powder, granules, encapsulated granules, pellets, tablets, dry flowable, wettable powder and water dispersible granules.
  • preferred formulation for the synergistic insecticidal combination is encapsulated granules (CG).
  • the synergistic insecticidal composition further comprises a plurality of different ingredients, such as surfactants, binders, stabilizers and carriers to form an encapsulated granular formulation.
  • a process for the preparation of a synergistic insecticidal composition comprising the steps of: (a) admixing Fipronil, Cartap Hydrochloride, surfactants, and stabilizers in a mixing vessel to form a first mixture; (b) homogenizing the first mixture to form a powder; (c) Admixing the powder, a carrier and a binder to form encapsulated granules.
  • a method for controlling insects at a locus comprising treating the locus with synergistic insecticidal composition comprising fipronil and cartap hydrochloride.
  • the synergistic insecticidal combination of the present invention is found to be useful in protecting a wide range of crops like fruits, vegetables, cereals etc. against major tissue-chewing, cutting, boring insects of plants from the insect Orders Orthoptera, Isoptera, Lepidoptera, Coleoptera, Hymenoptera, and Diptera etc.
  • CG formulation WDG formulation, WP formulation, SC formulation are the international denominations adopted by the FAO (Food and Agriculture Organization of the United Nations) to designate encapsulated granules, water dispersible granules, wettable powder and suspension concentrate, respectively.
  • FAO Food and Agriculture Organization of the United Nations
  • a novel synergistic insecticidal composition comprising fipronil, and cartap hydrochloride in a synergistic composition for the treatment of wide range of crops like fruited, vegetables, cereals etc. against major tissue-chewing, cutting, boring insects of plants from the insect Orders Orthoptera, Isoptera, Lepidoptera, Coleoptera, Hymenoptera, and Diptera etc.
  • synergistic composition wherein fipronil may be present in an amount of 0.1-10% w/w and more preferably in an amount of 0.5% w/w.
  • synergistic insecticide composition wherein cartap hydrochloride may be present in an amount of 1.0-25% w/w and preferably in an amount of 4.0% w/w.
  • the proportion of fipronil to cartap hydrochloride in the synergistic insecticidal composition in terms of mass is 1 : 15 to 1:8.
  • the synergistic insecticidal composition of present invention further comprises surfactants, stabilizers, binders and carriers.
  • the surfactant is Isopropyl acid phosphate and may be present preferably in an amount of 0.5-1.2% w/w and more preferably in an amount of 0.8% w/w.
  • the synergistic insecticidal composition of the present invention contains a stabilizer in order to protect the active compounds from thermal degradation and oxidation on storage.
  • Alkylphenol ethylene oxide is selected for use as stabilizer in the synergistic insecticidal combination and may be present preferably in an amount of 1.5-1.7% w/w and more preferable 1.7% w/w.
  • the synergistic insecticidal composition of the present invention also contains china clay as binder to bind the active ingredients to the carrier.
  • the carrier contemplated for the present investigation is preferably river sand.
  • the synergistic insecticidal composition comprising fipronil and cartap hydrochloride was formulated as encapsulated granules (CG). All the raw materials were verified for conformance to the laid out individual specification. The required quantities of raw materials were weighed, transferred through auto batching system into an agitating vessel and mixed for one hour. The quality of in-process sample was checked for conformance to the specification. The quality approved in-process sample was transferred to the holding vessel for packaging as per requirement.
  • compositions tabulated in each of the example 1 - 2 that are tabulated in Table 1 are formulated as encapsulated granule (CG).
  • Fipronil and Cartap Hydrochloride (Table 2) are blended with isopropyl acid phosphate and alkylphenol ethylene oxide (NP 85), and blended for one hour.
  • the mixture is homogenized using colloid mill and sieved to remove course particles.
  • the river sand (carrier) is added to the mixture and further blended for one hour.
  • China clay is further added to the mixture as binder and further blended for another half hour. Subsequently, the encapsulated granules are tested for quality control.
  • E Expected percentage of insecticidal control for the combination for the combination of the two insecticides at defined doses (for example equal to x and y respectively),
  • X X is the percentage of insecticidal control observed by the compound (I) at a defined dose (equal to x),
  • Y Y is the percentage of insecticidal control observed by the compound (II) at a defined dose (equal to y),
  • Fipronil 50 E a 40.31 - -
  • Cartap Hydrochloride 750 E b 50.09 - -
  • Fipronil 60 E a 42.80 - -
  • Cartap Hydrochloride 900 E b 67.71 - -
  • Fipronil 75 E a 46.93 - -
  • Fipronil 100 E a 54.65 - -
  • Cartap Hydrochloride 800 E b 58.28 - -
  • the paddy crop was transplanted in and harvested after 116 days. Application was made using broadcasting method. Experimental design was in randomized blocks with four replications and each plot measured an area of 100 sq. m. (10 x 10 m). The formulations tested were weighed according to doses and mixed in sand and applied using broadcasting method and evaluated for leaf folder and stem borer control in paddy. The reported results were mean of four replications of each evaluation designed in randomized complete blocks. The number of freshly folded leaves (caused by leaf folder) and dead hearts/white ear heads (caused by stem borer) was assessed at 5 DAA (days after application), 10 DAA and 15 DAA. Dead Heart (DH) and White Ear Head (WEH) as used to measure the effects of stem borer. Since the insect bores into the stem and cannot be counted therefore its effect is measured with dead heart/white ear heads.
  • Dead Heart DH
  • WEH White Ear Head
  • Leaf folder (Cnaphalocrosis medinalis) and Stem borer (Scirpophaga incertulas)
  • Table 4 Treatment details for evaluation of Bio-efficacy of new insecticide against leaf folder (Cnaphalocrosis medinalis) and stem borer (Scirpophaga incertulas) in Paddy
  • Table 5 The bio-efficacy effect of different treatment schedules against leaf folder and stem borer on paddy crop.
  • the sun dried grains obtained after threshing and cleaning from the harvested area of each plot were weighed for recording grain yield in each plot.
  • the grain yield thus obtained was then converted into kg hectare "1 for each plot.
  • the straw obtained after recovering grains from the harvested area of each plot was weighed for recording straw yield in each plot.
  • the straw yield thus obtained was then converted into kg hectare "1 for each plot.

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

L'invention concerne une nouvelle composition granulaire encapsulée synergique (GC) comprenant du pyrazole, du pyrrole ou du phénylimidazole à titre d'insecticide et du chlorhydrate de cartap, et un procédé de préparation associé.
PCT/IB2015/059438 2014-12-08 2015-12-08 Nouvelle composition granulaire encapsulée synergique WO2016092467A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN3589DE2014 2014-12-08
IN3589/DEL/2014 2014-12-08

Publications (1)

Publication Number Publication Date
WO2016092467A1 true WO2016092467A1 (fr) 2016-06-16

Family

ID=56106808

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2015/059438 WO2016092467A1 (fr) 2014-12-08 2015-12-08 Nouvelle composition granulaire encapsulée synergique

Country Status (1)

Country Link
WO (1) WO2016092467A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IN2006MU02156A (fr) * 2006-12-28 2007-12-24
WO2010095151A2 (fr) * 2009-02-20 2010-08-26 Deepak Pranjivandas Shah Composition granulaire hydro-dispersible
WO2012101659A1 (fr) * 2011-01-28 2012-08-02 Deepak Pranjivandas Shah Composition pesticide comprenant du soufre, un insecticide et un véhicule agrochimique

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IN2006MU02156A (fr) * 2006-12-28 2007-12-24
WO2010095151A2 (fr) * 2009-02-20 2010-08-26 Deepak Pranjivandas Shah Composition granulaire hydro-dispersible
WO2012101659A1 (fr) * 2011-01-28 2012-08-02 Deepak Pranjivandas Shah Composition pesticide comprenant du soufre, un insecticide et un véhicule agrochimique

Similar Documents

Publication Publication Date Title
CA2573806C (fr) Composition insecticide synergique contenant des composes chloronicotynyle et pyrethroide
EP2667719B1 (fr) Composition pesticide comprenant du soufre, un insecticide et un véhicule agrochimique
CN1317245B (zh) 处理和控制危害庄稼的节肢动物的方法以及适用于该方法的组合物
PT2319313T (pt) Combinações de substâncias ativas fungicidas contendo fluoxastrobina e fenamidona
JP5539899B2 (ja) アリ防除法
US7445791B2 (en) Synergistic insecticidal composition containing Chloronicotynyle and Organosphosphorus compounds
US20210145003A1 (en) Mixtures comprising a herbicide and a nitrification inhibitor such as 2-(3,4-dimethyl-1h-pyrazol-1-yl)succinic acid (dmpsa) or 3,4-dimethyl pyrazolium glocolate (dmpg)
KR101208335B1 (ko) 메타미포프(Metamifop)를 유효성분으로 함유하는 상승적 작용성을 지닌 제초제 조성물
US8142802B2 (en) Insecticidal composition with enhanced synergistic activity
WO2016092467A1 (fr) Nouvelle composition granulaire encapsulée synergique
JPS6368505A (ja) 農業用殺虫殺菌組成物
KR101214412B1 (ko) 서방화 농약 제제 및 이것을 사용한 수도병해충 방제 방법
Sulagitti et al. Management of Rice Leaffolder, Cnaphalocrocis medinalis (Guenee)(Pyralidae: Lepidoptera) with Phenyl Pyrazole and Neonicotinoids.
CN108157371B (zh) 一种用于种子包衣剂的农药组合物
JPS5942308A (ja) 農園芸用殺菌組成物
JP4602491B2 (ja) 害虫駆除剤
CN111789127A (zh) 一种含有茚虫威和环溴虫酰胺的杀虫组合物及其用途
WO2019030650A1 (fr) Composition pesticide et son procédé de préparation
JPS5829762B2 (ja) 農園芸用殺菌性組成物
JPH10507775A (ja) 有害生物駆除性オキサジアジン類
JPS5916805A (ja) 水稲用除草剤組成物
CN107258807A (zh) 一种含吡虫啉和高效氯氟氰菊酯的杀虫组合物
JPS5982308A (ja) 殺虫剤組成物
JPH03157302A (ja) 殺虫及び殺ダニ用組成物
JPS604162B2 (ja) 農園芸用除草組成物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 15867187

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 15867187

Country of ref document: EP

Kind code of ref document: A1