WO2019179309A1

WO2019179309A1 - Pesticidal compositions having emamectin benzoate and indoxacarb and methods for using such compositions

Info

Publication number: WO2019179309A1
Application number: PCT/CN2019/077085
Authority: WO
Inventors: James Timothy Bristow
Original assignee: Jiangsu Rotam Chemistry Co., Ltd
Priority date: 2018-03-22
Filing date: 2019-03-06
Publication date: 2019-09-26
Also published as: CN111836544A

Abstract

A pesticide composition comprising a diol compound, xanthan gum, emamectin benzoate and indoxacarb is provided. A method for protecting a plant from insect infestation or for treating a plant already infested with insects comprising applying the pesticide composition to such plants, plant parts and their surroundings is also provided.

Description

PESTICIDAL COMPOSITIONS HAVING EMAMECTIN BENZOATE AND INDOXACARB AND METHODS FOR USING SUCH COMPOSITIONS

CROSS REFERENCE TO RELATED APPLICATIONS

This application claims the priority of IN Patent Application No. 201821010554, filed on March 22, 2018 and titled with “PESTICIDAL COMPOSITIONS HAVING EMAMECTIN BENZOATE AND INDOXACARB AND METHODS FOR USING SUCH COMPOSITIONS” , and the disclosures of which are hereby incorporated by reference.

FIELD

This invention relates to a pesticidal composition having emamectin benzoate and indoxacarb, and methods for using such compositions.

BACKGROUND

Many agricultural pesticides, including insecticides, fungicides, herbicides, miticides and plant growth regulators, are formulated as suspension concentrates. The liquid compositions typically comprises one or more adjuvants intended to improve one or more properties of the composition, such as storage stability, ease of handling, pesticide efficacy against target organisms.

Chemical control is an important way for preventing and controlling pests in agriculture. However, current chemicals show unsatisfactory effects to certain kinds of pests. Furthermore, many pests have developed resistance to commonly used pesticides due to a long term use of the pesticides. Therefore, there is an urgent need to develop new methods and pesticide composition containing them to control these pests.

Emamectin benzoate, having CAS number: 155569-91-8, is a potent insecticide which controls many pests such as thrips, leafminers, and worms including alfalfa caterpillar, beet armyworm, cabbage looper, corn earworm, cutworms, diamondback moth, tobacco budworm, tomato fruitworm and tomato pinworm. Emamectin benzoate is described in U.S. Pat. No. 5,288,710.

Indoxacarb (methyl (4aS) -7-chloro-2, 5-dihydro-2- [ [ (methoxycarbonyl) [4- (trifluoromethoxy) phenyl] amino] carbonyl] indeno [1, 2-e] [1, 3, 4] oxadiazine-4a (3H) -carboxylate) is a potent insecticide. Indoxacarb was first launched by DuPont in Spain in 1998 as Avaunt ^TM for use on cotton, and as Steward ^TM for use on vines, apples and pears. It has a novel mode of action, now known to be through blocking of sodium channels in the nerve cells, leading to paralysis and death of the target insect. Indoxacarb is a semicarbazone compound developed for use against Lepidopteran species. It demonstrates effective control of lepidopteran insects including Cydia, Helicoverpa, Heliothis, Lobesia, Plutella and Spodoptera spp. Safety and environmental profiles lend the product to use in IPM programmes. In the United States, indoxacarb was approved as a reduced risk pesticide in 2000 as Steward ^TM for cotton and as Avaunt ^TM for fruit and vegetables.

The combination of the two pesticides are used in the prior art. However, there is still a risk of development of resistant insect subpopulations and the efficacy is still not so satisfied.

Therefore, there is a continuing interest in seeking a pesticide composition that exhibits improved properties.

SUMMARY

The inventor found surprisingly that the adjuvant combination of a diol compound and xanthan gum can increase greatly and significantly the efficacy of the active ingredient combination of emamectin benzoate and indoxacarb.

In a first aspect, the present invention is directed to an adjuvant composition comprising,

(a) one or more diol compounds of formula (I)

wherein R1 and R2 are independently selected from the group consisting of H and a (C1-C20) alkyl, and

(b) xanthan gum.

In a second aspect, the present invention is directed to a pesticide composition, comprising:

(a) one or more diol compounds of formula (I)

wherein R1 and R2 are independently selected from the group consisting of H and a (C1-C20) alkyl,

(b) xanthan gum,

(c) an effective amount of emamectin benzoate, and

(d) an effective amount of indoxacarb.

In a third aspect, the present invention is directed to a method for protecting a plant from insect infestation or for treating a plant already infested with insects, comprising applying the above described pesticide composition to such plants, plant parts and/or their surroundings. In some preferred embodiments, the plant is a crop.

"Plant" as used herein, refers to all plant and plant populations such as desired and undesired wild plants or crop plants.

"Plant parts" as used herein, refers to all parts and organs of plants, such as shoot, leaves, needles, stalks, stems, fruit bodies, fruits, seeds, roots, tubers and rhizomes. Harvested materials, and vegetative and generative propagation materials, for example, cutting, tubers, meristem tissue, rhizomes, offsets, seeds, single and multiple plant cells and any other plant tissues, are also included.

The word “surroundings” refers to the place on which the plants are growing, the place on which the plant propagation materials of the plants are sown or the place on which the plant propagation materials of the plants will be sown.

DETAILED DESCRIPTION

As used herein, the terminology "alkyl" is to be understood as a straight-chain or branched hydrocarbon radical which is substituted or unsubstituted, preferably having 1, 2, 3…, 19, and 20 carbon atoms, for example methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl and tert-butyl radicals. Correspondingly, alkyl radicals having a greater range of carbon atoms are to be understood as straight-chain or branched saturated hydrocarbon radicals which contain a number of carbon atoms which corresponds to this range.

Diol compounds are generally known compounds. In one embodiment, the diol compounds having a formula (I) :

in which R1 and R2 are independently selected from the group consisting of H and a (C1-C20) alkyl, wherein the C1-C20 alkyl may be unsubstituted or substituted.

In some preferred embodiments, R1, R2 are independently H or (C1-C10) alkyl, each of which is unsubstituted. More preferably, R1 and R2 are H or (C1-C5) alkyl, each of which is unsubstituted. Most preferably, R1 is H and R2 is H. Compounds with unsubstituted R1 and R2 are preferred.

Preferably, the number of carbon in R1 and R2 is not the same. The total number of carbon in R1 and R2 is ranged from 0 to 20, preferably ranged from 0 to 10, more preferably ranged from 0 to 5, still more preferably less than 3, most preferably the total number of carbon in R1 and R2 is equal to 0.

Preferably, the formula (I) is

Xanthan gum is generally known compounds having CAS number of 11138-66-2. Xanthan gum is a polysaccharide with a wide variety of uses, including as a common food additive. In the agrochemical industry, it is known as thickening agent.

The adjuvant composition comprises a non-zero amount of the one or more diol compounds and a non-zero amount of xanthan gum. As used herein, “non-zero amount” means an amount greater than 0.

In one embodiment, the adjuvant composition comprises, based on gram per liter (g/L) of the adjuvant composition:

(a) greater than or equal to about 1 g/L, more preferably from about 1 g/L to about 150 g/L, even more preferably from about 1 g/L to about 100 g/L, still more preferably from about 10 g/L to about 75 g/L or from about 15 g/L to about 50 g/L, most preferably from about 30 g/L to about 50 g/L, of one or more diol compounds; and

(b) greater than or equal to about 0.1 g/L, more preferably from about 0.1 g/L to about 20 g/L, even more typically from about 1 g/L to about 15 g/L, and still more typically from about 1 g/L to about 10 g/L or from about 1 g/L to about 5 g/L, most preferably from about 1.2 g/L to about 3 g/L, of xanthan gum.

In some embodiments, the adjuvant composition comprises:

about 30 g/L to about 50 g/L of one or more diol compounds and about 1.2 g/L to about 3 g/L of xanthan gum; preferably,

about 40 g/L of one or more diol compounds and about 2.5 g/L of xanthan gum.

The pesticide compositions according to the present invention are suitable for following plants of the crops: cereals (wheat, barley, rye, oats, corn, rice, sorghum, triticale and related crops) ; fruit, such as pomes, stone fruit and soft fruit, such as apples, grapes, pears, plums, peaches, papayas, almonds, pistachio, cherries, and berries, for example strawberries, raspberries and blackberries, bell pepper, red pepper; leguminous plants (beans, lentils, peas, soybeans, dry beans) ; oil plants (rape, mustard, sunflowers) ; cucurbitaceae (marrows, cucumbers, melons) ; sugarcane; fibre plants (cotton, flax, hemp, jute) ; citrus, such as calamondin, citrus citron, citrus hybrids (includes chironja, tangelo, tangor) , grapefruit, kumquat, lemon, lime, mandarin (tangerine) , sour orange, sweet orange, pummelo, and satsuma mandarin; vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika) ; coffee; as well as ornamentals (flowers, such as rose, shrubs, broad-leaved trees and evergreens, such as conifers) . Preferably, the crops are cereals, cucurbitaceae, fibre plants, fruits, oil plants, soybean and vegetables. Most preferred crops are cereals and vegetables.

The pesticide compositions of the present invention can be used to control a very wide variety of insects, for examples,

Alabama spp., Cnaphalocrosis spp., Cryptoblades spp., Diaphania spp., Dione spp., Dysdercus spp., Helicoverpa spp., Heliothis spp., Hellula spp., Mamestra spp., Neoleucinodes spp., Ostrinia spp., Paramadarus spp., Pectinophora spp., Phthorimaea spp., Pieris spp., Pleuroprucha spp., Plutella spp., Pseudoplusia spp., Spodoptera spp., Trichoplusia spp., Alabama argillacea, Cnaphalocrosis medinalis, Cryptoblades gnidiella, Diaphania nitidalis, Dione juno juno, Dysdercus spp., Helicoverpa armigera, Helicoverpa zea, Heliothis armigera, Heliothis virescens, Hellula phidilealis, Mamestra brassicae, Neoleucinodes elegantalis, Ostrinia nubilalis, Paramadarus complexus, Pectinophora gossypiella, Phthorimaea operculella, Pieris brassicae, Pieris rapae, Pleuroprucha asthenaria, Plutella xylostella, Pseudoplusia includens, Spodoptera exigua, Spodoptera frugiperda, Spodoptera littoralis, Trichoplusia ni, Tuta absoluta and Tuta spp.

As used herein, the terminology “effective amount” in reference to the relative amount of emamectin benzoate and indoxacarb in a pesticide composition means the relative amount of emamectin benzoate and indoxacarb that is effective to prevent and/or control insect, when the pesticide composition is applied to the insect at a given application rate.

The pesticides are emamectin benzoate and indoxacarb insecticides and the pesticide composition is an insecticidal composition that comprises an insecticidally effective amount of emamectin benzoate and indoxacarb.

In one embodiment, the pesticide composition comprises, based on gram per liter (g/L) of the pesticide composition:

(a) greater than or equal to about 1 g/L, more preferably from about 1 g/L to about 150 g/L, even more preferably from about 1 g/L to about 100 g/L, still more preferably from about 10 g/L to about 75 g/L or from about 15 g/L to about 50 g/L, most preferably from about 30 g/L to about 50 g/L, of one or more diol compounds,

(b) greater than or equal to about 0.1 g/L, more preferably from about 0.1 g/L to about 20 g/L, even more typically from about 1 g/L to about 15 g/L, and still more typically from about 1 g/L to about 10 g/L or from about 1 g/L to about 5 g/L, most preferably from about 1.2 g/L to about 3 g/L, of xanthan gum;

(c) an effective amount of emamectin benzoate; and

(d) an effective amount of indoxacarb.

The effective amount of emamectin benzoate means an amount greater than or equal to about 5 g/L, more preferably from about 5 g/L to about 800 g/L, even more typically from about 10 g/L to about 400 g/L, and still more typically from about 15 g/L to about 200 g/L or from about 20 g/L to about 100 g/L, most preferably from about 25 g/L to about 40 g/L, of emamectin benzoate.

The effective amount of indoxacarb means an amount greater than or equal to about 5 g/L, more preferably from about 5 g/L to about 800 g/L, even more typically from about 10 g/L to about 500 g/L, and still more typically from about 50 g/L to about 250 g/L or from about 50 g/L to about 200 g/L, most preferably from about 75 g/L to about 150 g/L, of indoxacarb.

The weight ratio of the diol compound of formula (I) to xanthan gum in the adjuvant composition or the pesticide composition is ranged from about 50: 1 to about 1: 1, preferably from about 25: 1 to 1: 1, more preferably from about 20: 1 to about 10: 1, most preferably about 16: 1.

The weight ratio of the diol compounds to indoxacarb is ranged from about 1: 1 to about 1: 10, preferably from about 1: 2 to about 1: 5, more preferably from about 1: 2 to about 1: 4, most preferably about 1: 3.

The weight ratio of the diol compounds to emamectin benzoate is ranged from about 1: 1 to about 10: 1, preferably from about 1: 1 to about 5: 1, more preferably from about 1: 1 to about 2: 1, most preferably about 1.33: 1.

The ratio in weight of the diol compound: xanthan gum: indoxacarb plus emamectin benzoate is about 16: 1: 60.

In one embodiment, the pesticide composition is spray applied to target plants, plant parts and/or their surroundings at a rate of from about 1 gram/hectare (g/ha) to about 500 g/ha of emamectin benzoate, preferably from about 1 gram/hectare (g/ha) to about 400 g/ha of emamectin benzoate, more preferably from about 10 gram/hectare (g/ha) to about 300 g/ha of emamectin benzoate.

In one embodiment, the pesticide composition is spray applied to target plants, plant parts and/or their surroundings at a rate of from about 1 gram/hectare (g/ha) to about 300 g/ha of indoxacarb, preferably from about 1 gram/hectare (g/ha) to about 150 g/ha of indoxacarb, more preferably from about 1 gram/hectare (g/ha) to about 100 g/ha of indoxacarb.

The adjuvant and pesticide compositions of the present invention may each, optionally, further comprise one or more agronomically acceptable adjuvant, for examples, a dispersing agent, an emulsifier, an pH regulator, and/or a filler.

In one embodiment, the pesticide composition further comprises a fertilizer, a fungicide, a herbicide, and/or a nematicide.

The adjuvant composition of the present invention can be made by combining and mixing the components of such composition.

The pesticide composition of the present invention can be made by mixing the ingredients together. In one embodiment, the pesticide composition is made by combining and mixing the adjuvant composition of the present invention, pesticide compounds, and water. Alternatively, the pesticide composition is made by combining and mixing the separate components of the adjuvant composition, pesticides, and water.

The pesticide composition of the present invention can be formulated in liquid or solid form, preferably as water-dispersible granule formulation, suspension concentrate, emulsifiable concentrate or wettable powder.

The composition according to the invention is especially advantageous for protecting crops from infestation or for treating crops already infested with insects.

EXAMPLES

EXAMPLE 1

Suspension concentrates (SC) formulations were prepared by mixing finely ground active ingredient with auxiliaries according to Table 1.

Larvae of beet armyworm (Spodoptera exigua) was reared in the laboratory. The insect were counted, collected and then put on healthy young lettuce plants. Formulations were diluted and then sprayed on the plants. After staying in a greenhouse at 21-25 ℃ and 80 %relative atmospheric humidity for 10 days, the remaining population was examined. The results are shown in Table 1.

Table 1.

EXAMPLE 2

Suspension concentrates (SC) formulations were prepared by mixing finely ground active ingredient with auxiliaries according to Table 2.

Larvae of diamondback moth (Plutella xylostella) was reared in the laboratory. The insects were counted, collected and then put on healthy young cabbage plants. Formulations were diluted and then sprayed on the plants. After staying in a greenhouse at 21-25 ℃ and 80 %relative atmospheric humidity for 10 days, the remaining population was examined. (Table 2)

Table 2.

EXAMPLE 3

Suspension concentrates (SC) formulations were prepared by mixing finely ground active ingredient with auxiliaries according to Table 3.

Pickleworm (Diaphania nitidalis) was reared in the laboratory. The number of insect were counted, collected and then put on healthy young cucumber plants. Formulations were diluted and then sprayed on the plants. After staying in a greenhouse at 21-25 ℃ and 80 %relative atmospheric humidity for 10 days, the remaining population was examined. (Table 3)

Table 3.

All publications, patents and patent applications cited in this specification are herein incorporated by reference as if each individual publication or patent application were specifically and individually indicated to be incorporated by reference. Although the foregoing invention has been described in some detail by way of illustration and example for purposes of clarity of understanding, it will be readily apparent to those of ordinary skill in the art in light of the teachings of this invention that certain changes and modifications may be made thereto without departing from the spirit or scope of the appended claims.

Claims

A pesticide composition, comprising:

(a) one or more diol compounds of formula (I)

wherein R1 and R2 are independently selected from the group consisting of H and a (C1-C20) alkyl,

(b) xanthan gum,

(c) emamectin benzoate, and

(d) indoxacarb.
The pesticide composition according to claim 1, wherein the weight ratio of the diol compound of formula (I) to xanthan gum is ranged from about 50: 1 to about 1: 1, preferably from about 20: 1 to about 10: 1.
The pesticide composition according to claim 1, which is in form of liquid and comprises about 30 g/L to about 50 g/L of diol compounds and about 1.2 g/L to about 3 g/L of xanthan gum; preferably, comprising about 40 g/L of diol compounds and about 2.5 g/L of xanthan gum.
The pesticide composition according to any one of claims 1 to 3, wherein the diol compound of formula (I) is
The pesticide composition according to any one of claims 1 to 4, further comprising one or more agriculturally acceptable adjuvant.
The pesticide composition according to claim 5, wherein the one or more agriculturally acceptable adjuvant is one or more of a dispersing agent, an emulsifier, an pH regulator, a filler, or combinations thereof.
The pesticide composition according to any of claims 1 to 6, further comprising one or more of fertilizer, fungicide, herbicide, and nematicide.
The pesticide composition according to any of claims 1 to 7, formulated in liquid or solid form, preferably as water-dispersible granule formulation, suspension concentrate, emulsifiable concentrate or wettable powder.
An adjuvant composition, comprising:

(a) one or more diol compounds of formula (I)

wherein R1 and R2 are independently selected from the group consisting of H and a (C1-C20) alkyl, and

(b) xanthan gum.
A method for protecting a plant from insect infestation or for treating a plant already infested with insects, comprising applying the pesticide composition according to any one of claims 1 to 8 to such plants, plant parts and/or their surroundings.
The method according to claim 10, wherein the plant is selected from the group consisting of cereals, citrus, coffee, cucurbitaceae plants, fibre plants, fruits, leguminous plants, sugarcane and vegetables.