CN1273018C - Insecticide composition - Google Patents

Insecticide composition Download PDF

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Publication number
CN1273018C
CN1273018C CNB028185838A CN02818583A CN1273018C CN 1273018 C CN1273018 C CN 1273018C CN B028185838 A CNB028185838 A CN B028185838A CN 02818583 A CN02818583 A CN 02818583A CN 1273018 C CN1273018 C CN 1273018C
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oil
insecticides
compound
composition
general formula
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CNB028185838A
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CN1556671A (en
Inventor
F·达奇
E·拉姆普
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Bayer LLC
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Bayer CropScience SA
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    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

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  • 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

The subject of the present invention is an insecticidal composition useful for controlling ravaging or pest arthropods, in particular insects, and more especially those which attack crops, the said composition combining at least one insecticidal compound of general formula (I) as in the description with an oil of plant origin possessing high drying power.

Description

Insecticides
The present invention relates to be used to control the insecticides of the disaster of arthropod, particularly a kind of insecticides, described composition contains phenyl pyrazole compounds as active substance, and unites with the oils adjuvant.
Insecticides contains known phenyl pyrazole compounds; especially disclosed a kind of compound 5-amino-3-cyano group-1-(2 that contains among the EP 029511; 6-dichlor-4-trifluoromethyl phenyl)-and the insecticides of 4-trifluoromethyl sulfinyl pyrazole, said composition is commonly called sharp strength spy (fipronil).A kind of phenyl pyrazole compounds that also can be used as active component in insecticides of just knowing recently is 5-amino-3-cyano group-1-(2,6-dichlor-4-trifluoromethyl phenyl)-4-ethyl sulfinyl pyrazoles.This compound is commonly called ethiprole, and discloses in United States Patent (USP) 5814652.
For control crops disaster, need to reduce the dosage that is sprayed at the chemical products in the environment, especially reduce using dosage.For accomplishing this point, some can be called the adjuvant of bio-stimulant, as mineral oil, wetting agent, bleeding agent, mix with commercial product, can accomplish this point now, for example, the adjuvant of mineral oil type is mixed with Pesticidal compound, so just can reduce the dosage of compound used therefor.This has also enlarged peasant's range of choice, so that they find the most suitable their solution of particular problem.On the other hand, when on some crops, finding phytotoxicity, just can limit the use that some have the product of these characteristics.
We find even the gained insecticides is also selective to so-called selectivity crops, thereby can keep the biologically active identical to the target disease when specific adjuvant is mixed with phenyl pyrazole compounds.
Therefore, the invention provides a kind of insecticides, described composition contains compound and a kind of oil of general formula (I), and described oil is from plant and have high drying capacity.
Wherein, R 1Represent halogen atom ,-CN or methyl or-C (S) NH 2,-C (=N-Y) Z or C (O) CH 3
R 2Representative-S (O) nR 3Or 4,5-dicyano imidazole-2-base or haloalkyl;
R 3Represent alkyl or haloalkyl;
R 4Be selected from hydrogen atom, halogen atom, hydroxyl or alkoxyl, and can be-NR 5R 6, C (O) R 7-C (O) OR 7,-S (O) mR 7, alkyl, haloalkyl ,-OR 8Or-N=C (R 9) (R 10);
R 5And R 6Independently be selected from hydrogen atom, alkyl, haloalkyl ,-C (O) alkyl, alkoxy carbonyl group, alkoxyalkyl-C (O)-or-S (O) rCF 3Or R 5And R 6Form a bilvalent radical together, this bilvalent radical can be disconnected as oxygen or sulphur by one or more hetero atoms.
R 7Be selected from alkyl and haloalkyl;
R 8Be selected from alkyl, haloalkyl and hydrogen atom;
R 9Be selected from hydrogen atom and alkyl;
R 10Be selected from phenyl and by one or more hydroxyls, halogen atom ,-the O-alkyl ,-S-alkyl, cyano group or alkyl or the optional heteroaryl that replaces of its combination;
X is selected from nitrogen-atoms and C-R 12
Y is selected from hydroxyl, amino, amino carbonyl, alkoxyl, aryl carbonyl, alkyl-carbonyl, alkoxy carbonyl group, carbamoyl, aryl-amino-carbonyl, alkyl-carbamoyl and pyrazolyl, and it can be substituted or not be substituted;
Z is selected from hydroxyl, amino, amino carbonyl, alkoxyl, aryl carbonyl, alkyl-carbonyl, alkoxy carbonyl group, carbamoyl, aryl-amino-carbonyl and alkyl-carbamoyl;
R 11And R 12Independently be selected from halogen atom or hydrogen atom or-CN or-NO 2
R 13Be selected from halogen atom, haloalkyl, halogenated alkoxy ,-S (O) qCF 3With-SF 5
M, n, q, r independently are selected from 0,1 and 2; Condition is to work as R 1When being methyl, R 3Be haloalkyl, R 4Be-NH 2, R 11Be Cl, R 13Be-CF 3, X is N;
The present invention is the insecticides of a kind of effective protection crops, and said composition is based on phenyl pyrazole compounds and a kind of adjuvant that derives from the vegetable oil type with high drying capacity.Known many agricultural chemical compounds that is used for, the especially vegetable oil of Pesticidal compound preparation are for example from United States Patent (USP) 6149913.Yet, be not reported in and used vegetable oil in the insecticides with high drying capacity.Therefore, making us very surprised is that this application in insecticides of the present invention may obtain very favorable result.
In addition, the composition of this preparation can make this plant protection mixture that extraordinary quality is arranged and it be can be used in various other commercial compositions and not have the inconsistent risk of physico chemistry.The stability of this plant protection mixture also makes it possible to prepare some active component when using insecticides of the present invention, these active components otherwise be difficult to use or even can't use.
Insecticide of the present invention contains the compound of general formula I and the oil of plant origin.With regard to the compound of general formula I, the alkyl of formula (I) and preferred low alkyl group of alkoxyl and alkoxyl promptly contain the base of 1-4 carbon atom; Haloalkyl and halogenated alkoxy equally preferably contain 1-4 carbon atom; Haloalkyl and halogenated alkoxy can have one or more halogen atoms; Preferred such base comprises-CF 3With-OCF 3
The compound of preferred general formula I is to work as R 1Be-during CN; R 2Be-S (O) nR 3R 3Be alkyl or haloalkyl; R 4Be-NR 5R 6R 5With regard to R 6Independently be selected from hydrogen atom, alkyl, haloalkyl ,-C (O) alkyl and C (O) OR 7R 7Be alkyl or haloalkyl; X representative-C-R 12R 13It is haloalkyl; R 11And R 12Independently be selected from halogen atom or hydrogen atom or-CN or-NO 2
The compound of first kind of particularly preferred general formula I is (1), works as R 1Be-during CN; R 2Be-S (O) 2CF 3R 4Be-NH 2X is-C-Cl; R 11Be chlorine, R 13It is methyl chloride.The chemical name of this compound is 5-amino-3-cyano group-1-(2,6-dichlor-4-trifluoromethyl phenyl)-4-trifluoromethyl sulfinyl pyrazole, and is called sharp strength spy.
The compound of second kind of particularly preferred general formula I is to work as R 1Be-during CN; R 2Be-S (O) 2C 2H 5R 4Be-NH 2X is-C-Cl; R 11Be chlorine, R 13It is methyl chloride.The chemical name of this compound is 5-amino-3-cyano group-1-(2,6-dichlor-4-trifluoromethyl phenyl)-4-ethyl sulfinyl pyrazoles, and is called ethiprole.
Second kind of oil that component is a plant origin of described composition.According to the present invention, use the advantage of vegetable oil to be, compare their avirulences or be hypotoxic at least, and low phytotoxicity and higher biodegradability is arranged with mineral oil.Described oil can be the mixing of undersaturated vegetable oil, isomerized oil, vegetable oil esters, vegetable polymer or these different organic faciess.
Described oil can have various sources, but is preferred from the oil of linseed, sunflower, soybean, corn, cottonseed, safflower and rape seed.
These oil can be various grades, are called rough, refining or isomerized.Preferably, described oil is the natural polyunsaturated vegetable oil that contains a large amount of unsaturated bonds.The statement polyunsaturated oil is meant a kind of triglycerides, and wherein most of linear aliphatic chains have two or three two keys in every chain, be expressed as C18:2 or C18:3, and this represents that this chain contains 18 carbon atoms and 2 or 3 two keys are arranged.The example of polyunsaturated oil class has the triglycerides that mainly contains so-called linoleic acid type fatty acid chain (C18:3), as linseed oil.As guide, this oil composition of representing the fatty acid feature by weight is in following scope: 50 to 60%C18:3-10 to 17%C18:2-15 to 25%C18:1-2 to 4%C18:0-5 to 8%C16:0.The example of polyunsaturated oil class has the triglycerides that mainly contains so-called linoleic acid type fatty acid chain (C18:2), as sunflower oil, corn oil, soybean oil, safflower oil, cottonseed oil and rapeseed oil.As guide, oil compositions of these expression fatty acid features are in following scope: 45 to 70%C18:2-0.1 to 10%C18:3-10 to 40%C18:1-0.1 to 10%C18:0-1 to 26%C16:0.In other words, the oil in the above-mentioned scope of the present invention is called as drying oil.
Drying capacity is natural (drying oil or a semi-drying oil) or little or do not have the oil (so-called semi-drying oil or nondrying oil) of drying capacity to obtain by the chemical treatment drying capacity; Then with this oily isomerization.Isomerization reaction comprises the two key-C=CH-CH that make fatty acid chain 2-CH=CH-conjugation is to obtain the diene-CH=CH-CH=CH-CH of following conjugation 2-, can improve its drying capacity (with the reactivity of air) like this.What deserves to be mentioned is that as isomerized oil, isomerized sunflower oil has the conjugated diene of 16-18%, and isomerized linseed oil contains the conjugated diene of 11-13%.
As for composition of the present invention, preferably use the vegetable oil of iodine number (relevant) greater than 70 with its drying capacity, more preferably greater than 90, be preferably more than 130 again, most preferably be greater than 150.
The preferably refining and/or isomerized sunflower oil of described oil.
In the composition of the present invention, oil is that 0.15-1.6 is suitable with the ratio of the compound of general formula I, preferably from 0.2 to 1.35, more preferably from 0.25 to 1.
Composition of the present invention is liquid, and can be the form of concentrate composition, promptly is mixed with the commercial product of the two material.It also can be the diluted composition that is easy to be sprayed on the plant to be processed.In the later case, the concentrate composition that contains these two kinds of materials that dilutable water is commercially available (this mixture is called as blending preparation (ready mix)), or dilution contains a kind of bucket mix formulation (tankmix) of commercially available concentrate composition of material respectively.
Fluid composition of the present invention can be the form of solution, suspension or emulsion or emulsible concentrate.Owing to be easy to use and make, oil-water fluid composition is preferred.Preferably adopt the aqueous suspensions concentrate of the O/w emulsion form of vegetable oil.
Composition of the present invention also can contain the solid or the liquid additive of prior art in the plant protection products prescription.Described composition can contain all to plant protection composition common additive or adjuvant, especially carrier, surfactant, adhesion promotor and incremental dose, antifreezing agent.
Said composition also can contain other composition, as protective colloid, adhesive, thickener, thixotropic agent, penetration enhancers, stabilizing agent, chelating agent, pigment, colouring agent, polymer, antifoaming agent.Term " carrier " is meant natural or synthetic organic or inorganic material in the present invention, and described active component combines with it and is beneficial to active component is used for plant.Therefore, carrier normally inertia and to be that agricultural goes up acceptable, especially on processed plant.Carrier can be solid (clay, natural or synthetic silicate, silica, resin, wax, solid fertilizer etc.) or liquid (water, alcohols, ketone, petroleum distillate, aromatic hydrocarbons or alkane, chlorinated hydrocabon, liquefied gas etc.).
Described surfactant can be emulsifier, dispersant or the wetting agent of ion or nonionic type.For example; can mention polyacrylate; ligninsulfonate; phenolsulfonate or naphthalene sulfonate; the condensation polymer of oxirane and fatty alcohol or fatty acid or fatty amine, the phenol of replacement (especially alkyl phenol or aryl phenol), the salt of esters of sulfosuccinic acids; the derivative of taurine (especially alkyl taurine ester), the alcohol of polyoxyethyleneization or the phosphide of phenol.Exist at least a surfactant well to be used for plant to promote active component to be dispersed in the water and with them.Term oil-aqueous suspensions composition is meant a kind of aqueous suspensions, and wherein solid active agent is suspended in water and the oil-containing organic facies with crystal form, is that vegetable oil adds emulsible material here, is the form of O/w emulsion.
Prepared the suspending concentrate that can use by spraying obtaining stable liquid form product, this product can thickening or is formed precipitation or be separated after storage, they contain the active component of 10-75%, the surfactant of 0.5-15%, the thixotropic agent of 0.1-10%, the additive that 0-10% is suitable, as pigment, colouring agent, antifoaming agent, corrosion inhibitor, stabilizing agent, penetration enhancers, adhesive and as the water or the organic liquid of carrier, described active component is almost insoluble or insoluble in this liquid.Some organic solid materials or inorganic salts can be dissolved or be dispersed in the carrier to prevent to precipitate or as the antifreezing agent of water.
Insecticides of the present invention can various known treatment methods be used for crops, as the liquid spray of composition as described in will the containing gas first portion to crops to be processed, sprays, and is expelled in the tree or smears.Is preferred processing method with liquid spray to the gas first portions of crops to be processed.
According to a further aspect of the invention, the arthropodan processing method that also provides a kind of control to harm the crops, described method are characterised in that the above-mentioned insecticides with effective and plant-less toxicity dosage is used for the gas first portion of plant.
Statement " effective and plant-less toxicity amount " is meant that the arthropods that the amount of the present composition can be enough to appearance maybe may be appeared on the crops is controlled or is killed, and described crops are not caused the phytotoxicity sign.According to contained compound in kind, weather conditions and the present composition of insect to be processed, crops, described dosage can change in the broader context; For example, described amount can be determined by the site test of system by the technical staff who is proficient in this field.
The dosage of the Pesticidal compound of used general formula I is 5-1000g/ha in the insecticides of the present invention, and it is favourable being preferably 10-250g/ha.The amount of suitable oil component be general formula I compound problem 0.25-0.45 doubly.Actual dose will be decided according to various factors, as plant to be processed, gradient of infection, weather conditions etc.
The crops that are fit to handle with the inventive method comprise cereal, especially barley, high protein and heavy oil plant, as pea, rape seed, sunflower, corn, grape, tomato, potato, vegetable crop (lettuce, cucurbitaceous plant etc.), paddy rice, arboriculture (apple tree, pear tree, cherry tree etc.), citrus fruit, turf (turf).
In processing method of the present invention, two kinds of insecticide ingredients of the present invention are to use simultaneously with the form of the present composition, and described composition is with being in harmonious proportion the preparation of concentrate or pot type mixture.
The present invention relates to the compound of the general formula I of using insecticides of the present invention for simultaneously, continuously or alternately and the product of oil on the other hand.
Below unrestricted embodiment disclosed the advantageous feature of the present composition.
Embodiment 1: the preparation of insecticides
Insecticides of the present invention contains following composition:
The pesticide active ingredient 375 of-general formula (I)
The poly-aryl phenol potassium phosphate 60 of-ethoxyquin
-dioctyl sodium sulphosuccinate salt 10
-ethoxyquin oleic acid 8.5
-polyunsaturated vegetable oil 170
-single propane diols 50
-polysaccharide 1.4
-1,2-benzisothiazole-3 ketone 0.7
-different three decyl alcohol 10
-citric acid monohydrate compound 1
-water (1 liter)
With the known method preparation, method is as follows:
The limit is stirred the poly-aryl phenol potassium phosphate, dioctyl sodium sulphosuccinate salt and the citric acid monohydrate compound that become single propane diols, different three decyl alcohol, ethoxyquin and is added in the water simultaneously.Continue to stir so that these compositions disperse and dissolving.Add active component then while stirring.With colloid mill suspension is ground in advance, wear into final size with ball mill then.In the suspension that grinds, add while stirring and contain 2% polysaccharide and 1%1, the solution of 2-benzisothiazole-3 ketone.Add oil phase that the uniform homogeneous blend by the oleic acid of vegetable oil and ethoxyquin constitutes while stirring to form O/w emulsion.
Embodiment 2
Two kinds of compositions of the present invention that contain rapeseed oil and soybean oil with the method preparation of embodiment 1.Following table 1 is described the composition of various prescriptions in detail.
Table 1
Composition 1 Composition 2
g/kg g/kg
5-amino-3-cyano group-1-(2,6-dichlor-4-trifluoromethyl phenyl)-4-ethyl sulfinyl pyrazoles Pesticidal compound 105.26 103.63
Through the rapeseed oil of selecting Vegetable oil with high drying capacity 200
Through the soybean oil of selecting Vegetable oil with high drying capacity 100
Soprophor FLK Dispersant 50 50
Geropon SDS Wetting agent 10 10
Alkamul A Emulsifier 15 15
Propane diols Antifreezing agent 55 20
Rhodorsil 454 Antifoaming agent 5.0 5.0
Rhodopol G Thickener 2.0 1.2
Proxel GXL Biocide 1.0 0.2
Water 586.74 586.74
Embodiment 3: the processing of rice crop
By application concentration on leaf is that the composition of the present invention 1 and 2 of 50g/ha is handled and is subjected to the high rice plant of about 16-17cm that little brown planthopper (Laodelphax striatellus) infects.Described insecticides is used with spray gun.
Observe insect mortality in 2 days.The results are shown in the following table 2.
Table 2
Insecticides Insecticide effect (6 hours) Insecticide effect (24 hours) Insecticide effect (48 hours)
Composition 1 31 100 100
Composition 2 27.6 100 100
The processing of embodiment 4 rice crops
By on leaf, use 25 and the composition of the present invention 1 and 2 of two kinds of concentration of 50g/ha handle and be subjected to the high rice plant of about 16-17cm that brown planthopper (Nilaparvata lugens) infects.Described insecticides is used with spray gun.
Experiment is as a comparison used rice crop and to be contained identical active component but the similar suspension composition of oily ingredient not.
Observe the insect number of every square metre of plant in 14 days.The results are shown in the following table 3.
Table 3
Insecticides
3 hours 1 day 3 days 7 days 10 days 14 days
Composition 1 (25g/ha) 1166 495 204 319 259 154
Composition 1 (50g/ha) 1194 495 165 358 215 110
Composition 2 (25g/ha) 1249 363 182 281 297 77
Composition 2 (50g/ha) 1089 336 160 176 110 55
Comparative composition (25g/ha) 1056 605 248 462 325 172
Comparative composition (50g/ha) 930 517 154 341 204 121
From The above results as seen, compare with the correspondent composition of oil-containing not, oil compositions of the present invention can provide and knock down activity preferably.

Claims (8)

1. insecticides; it is characterized in that; described composition contains Pesticidal compound and a kind of plant-derived oil with high drying capacity of the ethiprole of chemistry 5-amino by name-3-cyano group-1-(2,6-dichlor-4-trifluoromethyl phenyl)-4-ethyl sulfinyl pyrazoles as general formula (I).
2. insecticides as claimed in claim 1 is characterized in that the iodine number of described vegetable oil is greater than 70.
3. insecticides as claimed in claim 1 is characterized in that the iodine number of described vegetable oil is greater than 150.
4. as each described insecticides in the above-mentioned claim, it is characterized in that described vegetable oil is selected from linseed oil, sunflower oil, soya-bean oil, corn oil, cottonseed oil, safflower oil and rapeseed oil.
5. as each described insecticides in the above-mentioned claim, it is characterized in that the weight ratio of the compound of oil/general formula I is 0.15-1.6.
6. the arthropodan processing method that harms the crops of control is characterized in that, effectively and non-plant toxicity dosage be used to the gas first portion of plant as each described insecticides in the above-mentioned claim.
7. method as claimed in claim 6 is characterized in that, the dosage of the Pesticidal compound that is applied is, the compound of general formula I is 5-1000g/ha, and the dosage of oil be general formula I compound 0.25-0.45 doubly.
8. the compound and the oily product of the general formula I of insecticides of the present invention used in confession simultaneously, continuously or alternately.
CNB028185838A 2001-09-24 2002-09-23 Insecticide composition Expired - Fee Related CN1273018C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR01/12273 2001-09-24
FR0112273 2001-09-24

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CN1273018C true CN1273018C (en) 2006-09-06

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EP (1) EP1435783A1 (en)
JP (1) JP2005504107A (en)
KR (1) KR100952092B1 (en)
CN (1) CN1273018C (en)
CO (1) CO5570636A2 (en)
TW (1) TWI335208B (en)
WO (1) WO2003028465A1 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI484910B (en) 2006-12-01 2015-05-21 Du Pont Liquid formulations of carboxamide arthropodicides
CN102669190B (en) * 2012-05-11 2013-10-02 浙江农林大学 Botanical pesticide special for landscape plants and preparation method and use thereof

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6117854A (en) * 1997-08-20 2000-09-12 The Clorox Company Enhanced performance insecticide compositions containing plant derived oil carriers and methods of using the same
US6149913A (en) * 1998-11-16 2000-11-21 Rhone-Poulenc Ag Company, Inc. Compositions and methods for controlling insects

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JP2005504107A (en) 2005-02-10
TWI335208B (en) 2011-01-01
WO2003028465A1 (en) 2003-04-10
CN1556671A (en) 2004-12-22
KR20040033318A (en) 2004-04-21
EP1435783A1 (en) 2004-07-14
CO5570636A2 (en) 2005-10-31
KR100952092B1 (en) 2010-04-13

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