GB2220856A - Novel synergistic agricultural insecticidal and acaricidal combinations containing avermectin derivatives - Google Patents
Novel synergistic agricultural insecticidal and acaricidal combinations containing avermectin derivatives Download PDFInfo
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- GB2220856A GB2220856A GB8915734A GB8915734A GB2220856A GB 2220856 A GB2220856 A GB 2220856A GB 8915734 A GB8915734 A GB 8915734A GB 8915734 A GB8915734 A GB 8915734A GB 2220856 A GB2220856 A GB 2220856A
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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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
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- A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
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- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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- 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
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- A01N47/22—O-Aryl or S-Aryl esters thereof
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- 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
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- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
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- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
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Abstract
Novel combinations of agricultural insecticides, acaricides and pesticides have a synergistic effect against such agricultural insect and mite pests. Avermectin amino and alkylated amino derivates thereof, which are known to be highly effective, broad-spectrum agricultural pesticidal agents, are combined with compounds which are known to be active as agricultural insecticidal and acaricidal agents such as organotin, pyrethroid, organocarbamate, organophosphorous, insect growth regulator, formamidine and chlorinated hydrocarbon compounds. Such avermectin derivatives may also be combined which chitin synthesis inhibitors, ovicides, metabolic inhibitors, feeding stimulants and natural insecticidal agents. In combination, effects are observed which are greater than what could be expected from the individual compounds. Compositions containing such a synergistic combination of compounds as active ingredients are also disclosed.
Description
TITLE OF THE INVENTION
NOVEL SYNERGISTIC AGRICULTURAL INSECTICIDAL AND
ARCARICIDAL COMBINATIONS
BACKGROUND OF THE INVENTION
Avermectin compounds are a series of natural products isolated from the fermentation broth of a strain of Streptomyces avermitilis. The series consists of eight compounds, four major and four minor. The compounds are disclosed in U.S. Patent 4,310,519. Certain derivatives of such compounds are also disclosed, such as the 22,23-dihydro derivatives described in U.S. Patent 4,199,569. The 13-deoxy derivatives of avermectin compounds are disclosed in
U.S. Patents 4,171,314 and 4,173,571. The 4"-phosphate derivatives of the avermectin compounds with a 13-0-disaccharide group present, are disclosed in US Patent 4,469,682.In addition, the 4"-amino compounds and the 4"-alkylated amino compounds, the avermectin compounds of the instant combination, are disclosed in US patent 4,427,663.
The synergistic combinations also include organotin compounds such as Plictran (cyhexatin) and
Vendex (fenbutatin oxide) disclosed in The 1981 Farm
Chemicals Handbook, pages 268 and 359, respectively; synthetic pyrethroids, such as Ambush or Pounce (permethrin), Ammo or Cymbush (cypermethrin) and
Pydrin or Belmark (fenvalerate), disclosed in The 1981 Farm Chemicals Handbook, pages C256, C95 and
C148, respectively; chitin synthesis inhibitors such as Dimilin (diflubenzuron) disclosed in US patents; 3,748,356, 3,933,908, 3,989,842, and The 1981 Farm
Chemicals Handbook, page C115, and Nomolt (teflubenzuron) disclosed in Technical Information
Sheet of CME134 Celamerck, Inqelheim/Rhein, Germany; ovicides such as Savey (hexythiazox) disclosed in The 1987 Farm Chemicals Handbook, page C137, and Apollo (clofentezine) disclosed in The 1987 Farm Chemicals
Handbook, page C64; metabolic inhibitors such as
Butacide (piperonyl butoxide) disclosed in
The 1987 Farm Chemicals Handbook, pages E20 and E78, triphenyl phosphate disclosed in US patent 2,805,240; feeding stimulants such as Coax disclosed in The 1987
Farm Chemicals Handbook, page C65; and natural insecticides such as Dipel (Bacillus thurinqiensis) as disclosed in J. Agr. Food Chem 7, 687 (1959); organocarbamate compounds, such as Lannate (methomyl) disclosed in The 1981 Farm Chemicals Handbook, page
C215, Larvin (thiodicarb) disclosed in The 1987 Farm
Chemicals Handbook, pages C250 and E72, and Furadan (carbofuran) disclosed in The Pesticide Manual,
Worthing (Ed.) (1979) page 82; organophosphorous compounds, such as Orthene (acephate), Lorsban (chlorpyrifos), Thimet (phorate), Basudin (diazinon) and methylparathion disclosed in The 1981 Farm
Chemicals Handbook, pages C246, C77, C262, C107 and
C218, respectively; malathion, disclosed in The 1987
Farm Chemicals Handbook, pages C155 and E66, dimethoate disclosed in The 1987 Farm Chemicals
Handbook, pages C91 and E23, and Padan (cartap) disclosed in The Pesticide Manual, Worthing (Ed.) (1979) page 86; insect growth regulators, such as
Dimilin (diflubenzuron), also useful as an chitin synthesis inhibitor and discussed above; formamidine compounds, such as Mitac (amitraz) and Fundal (chlordimeform) disclosed in The 1981 Farm Chemicals
Handbook, pages C17 an C70, respectively, and chlorinated hydrocarbon compounds such as Kelthane (dicofol) and Acarol (bromopropylate) disclosed in
The 1981 Farm Chemicals Handbook pages C110 and C115, respectively, and Thiodan (endosulfan) disclosed in
US patent 2,983,732.
SUMMARY OF THE INVENTION
The instant disclosure describes certain synergistic combinations of avermectin compounds and organotin, pyrethroid, chitin synthesis inhibitor, ovicide, metabolic inhibitor, feeding stimulant, organocarbamate, organo-phosphorous, insect growth regulator, formamidine, tertiary amine and chlorinated hydrocarbon compounds and natural insecticidal agents which are referred to hereinafter as "combining compounds". Thus, it is an object of this invention to describe such synergistic combinations. It is a further object to describe the individual components of such synergistic combinations and the relative proportion of each component in the combination. A still further object of this invention is to describe the agricultural, insecticidal, acaricidal and pesticidal effects of such combinations.Further objects will become apparent from a reading of the following description.
DESCRIPTION OF THE INVENTION
The instant invention consists of a combination of avermectin compounds and combining compounds which have a synergistic effect when used in the control or elimination of infestations in domestic and agricultural environments. The avermectin compounds of this invention have the following formula:
wherein n is 0 or 1;
R1 is
R2 is hydrogen; the broken line indicates a single or a double bond; however, R2 is present only when the broken line indicates a single bond; and
R3 and R4 are independently hydrogen or loweralkyl.
The preferred avermectin compound is the 4"-epimethyl amino derivative of avermectin Bla/Blb.
That is the compound wherein R3 is hydrogen, R4 is methyl; the 4"-amino stereochemistry is ss, above the plane of the ring (the natural stereochemistry for the avermectin is a, below the plane of the ring); and n is both 0 and 1, that is the compound which is a mixture of the sec. butyl compound (n = 1) and the isopropyl compound (n = 0), in approximately an 80:20 ratio of sec-butyl to isopropyl compounds.
The combining compounds that constitute the second part of the instant synergistic combinations are exemplified by the representative compounds disclosed above in the Background of the Invention.
When used as agricultural insecticide or miticides the avermectin compounds are administered at dosage rates of from 1.0 to 50 g of the active compound per hectare. When used as agricultural insecticide agents the combining compounds are administered at dosage rates of from 10 to 2500 g of the active compound per hectare.
The synergistic effects of the combination of the avermectin compounds with the combining compounds are observed in providing for a reduced dosage of one or both of the components. Thus, a lessened quantity of the agricultural insecticide or acaricide is administered than normally would be required which results in a lessening of possible side effects and a lessening in the development of resistance. In addition, there is observed the synergistic expansion of the spectrum of activity on agricultural insect or mite pests which may be successfully combatted than would be expected from a consideration of the spectra of activity of the individual components. Thus, the possibility of eliminating agricultural insect and mite infestations against which the individual components are ineffective or only partially effective is realized in the instant synergistic combination.
The agricultural arthropod infestations against which the instant synergistic combination is particularly effective are Acarina such as
Tetranychus urticae, Panonychus ulmi, Panonychus citri, Phyllocoptruta oleivora and PoloPhaqotarsonemus latus; and the like; Coleoptera such as Leptinotarsa decemlineata, Phyllotrecta striolate; Lepidoptera such as podoptera exiqua, Plutella xvlostella, Pieris rapae, Heliothis virescens and H. zea; Diptera such as Liriomyza trifolii; Homoptera such as Psylla pyricola, Myzus pescicae, Brericoryne brassicae, Bemisia tabaci and Aphis gossypii, and the like;
Orthoptera such as Blattella germanica.
The instant synergistic combination is useful for controlling the above mite pests, and others, on economically useful crops such as maize, vegetables, cotton, deciduous fruit, citrus, tree nuts and vines.
In using the instant synergistic combination, the individual components are used in proportions which may extend to from 1 part of the avermectin compound to 2500 parts of combining compound to from 100 parts of the avermectin compound to 1 part of combining compound.
The synergistic composition is useful against insect and mite pests of stored grain and agricultural plants and immature stages of mites or insects living in or on plant tissue. When the synergistic composition is used to combat agricultural pests that inflict damage upon crops while they are growing or in storage, it is applied using known techniques such as sprays, granules, dusts, emulsions, and the like, to the growing plant or the soil in which it is planted, or to the stored crops to effect protection from such agricultural pests.
Specific formulations containing avermectin compounds and combining compounds which have synergistic agricultural, insecticidal, arcaricidal, pesticidal and miticidal effects are as follows:
Formulation 1 Weight 4"-epimethylamino-4"-deoxy 2.00
Avermectin Bla/Blb Dicofol 20.00
Xylenes 60.00
Emulsifier 18.00
Total 100.00
Formulation 2 Weight % 4"-epimethylamino-4"-deoxy 2.00
Avermectin Bla/Blb
Acarol 24.00
Xylenes 56.00
Emulsifier 18.00
Total 100.00
Formulation 3 Weight 4"-epimethylamino-4"-deoxy 2.00
Avermectin Bla/Blb
Chlorbenzilate 15.50
Xylenes 65.50
Emulsifier 17.00
Total 100.00
Formulation 4 Weight Chlordimeform 24.0 4 "-epimethylamino-4 "-deoxy 2.2
Avermectin Bla/Blb (91%)
Xylenes 61.8
Emulsifiers 12.0
Total 100.0
Formulation 5 Weight %
Amitraz 20.0 4"-epimethylamino-4"-deoxy 2.2
Avermectin Bla/Blb (91%)
Xylenes 65.8
Emulsifiers 12.0
Total 100.0
Formulation 6 Weight Malathion 20.0 4"-epimethylamino-4"-deoxy 2.2
Avermectin Bla/Blb (91%)
Xylenes 65.8
Emulsifiers 12.0
Total 100.0
Formulation 7 Weight %
Dimethoate 20.0 4"-epimethylamino-4"-deoxy 2.2
Avermectin Bla/Blb (91%) Xylenes 65.8
Emulsifiers 12.0
Total 100.0
Formulation 8 Weight %
Dimilin (98%) 25.5 4"-epimethylamino-4"-deoxy 2.0
Avermectin Bla/Blb (91%)
Attaclay 25.0
Diethylene glycol 4.0
Talc 28.0
Wetting agent 12.0
Dispersing agent 3.0
Oleic acid 0.5
Total 100.0
Formulation 9 Weight Dimilin (98%) 4.08 4"-epimethylamino-4"-deoxy 0.44
Avermectin Bla/Blb (91%)
Granular Montmorilionite Clay 89.48
Diethylene glycol 6.00
Total 100.00
Formulation 10 Weight Diazinon (87%) 54.0 4"-epimethylamino-4"-deoxy 2.2
Avermectin Bla/Blb (91%)
Xylenes 29.8
Emulsifier 14.0
Total 100.0
Formulation 11 Weight Methyl Parathion (80%) 25.0 4"-epimethylamino-4"-deoxy 2.2
Avermectin Bla/Blb (91%)
Xylenes 60.8
Emulsifier 12.0
Total 100.0
Formulation 12 Weight Chlorpyrifos 24.0 4"-epimethylamino-4"-deoxy 2.2
Avermectin Bla/Blb (91%)
Xylenes 61.8
Emulsifier 12.0
Total 100.0
Formulation 13 Weight Diazinon (87%) 5.75 4"-epimethylamino-4"-deoxy 0.33
Avermectin Bla/Blb (91%)
Montmorillonite granule 87.92
Diethylene glycol 6.00
Total 100.00
Formulation 14 Weight
Methomyl 24.0 4"-epimethylamino-4"-deoxy 2.2
Avermectin Bla/Blb (91%)
Attaclay 36.3
Kaolin 16.0
Wetting agent 12.0
Dispersing agent 3.0
Oleic acid 0.5
Diethylene glycol 6.0
Total 100.0
Formulation 15 Weight % Carbofuran 50.0 4"-epimethylamino-4"-deoxy 2.2
Avermectin Bla/Blb (91%)
Attaclay 19.8
Kaolin 6.5
Wetting agent 12.0
Dispersing agent 3.0
Oleic acid 0.5
Diethylene glycol 6.0
Total 100.0
Formulation 16 Weight % Weight % 4"-epimethylamino-4"-deoxy 2.2 2.2
Avermectin Bla/Blb Pl ictran 50.0
Vendex - 50.0
Attaclay 25.0 25.0
Kaolin 3.8 3.8
Diethylene glycol 4.0 4.0
Wetting agent 12.0 12.0
Dispersing agent 3.0 3.0
Total 100.0 100.0
Formulation 17-Liquid Weight % Weight % Weight % 4"-epimethylamino-4"- 2.2 2.2 2.2
deoxy Avermectin
Bla/Blb (91%)
Cypermethrin 20.0
Fenvalerate - 20.0
Deltamethrin - - 20.0
Xylenes 70.0 70.0 70.0
Emulsifier 8.0 8.0 8.0
Total 100.0 100.0 100.0
Formulation 18-Granular Weight % Weight % Weight % 4"-epimethylamino-4"- 0.33 0.33 0.33
deoxy Avermectin
Bla/Blb (91%)
Avermectin Bla/Blb (91%) 0.33 0.33 0.33 Cypermethrin 3.00
Fenvalerate - 3.00
Deltamethrin - - 3.00
Montmorillonite granule 90.67 90.67 90.67
Diethylene glycol 6.00 6.00 6.00
Total 100.00 100.00 100.00
Claims (3)
1. A synergistic agricultural, insecticidal, arcaricidal and pesticidal combination of ar avermectin compound having the formula:
wherein n is 0 or 1;
R1 is
R2 is hydrogen; the broken line indicates a single or a double bond; however, R2 is present only when the broken line .indicates a single bond; and R3 and R4 are independently hydrogen or lower alkyl; and a combining compound selected from the group consisting of organotin, pyrethroid, chitin synthesis inhibitor, ovicide, metabolic inhibitor, feeding stimulant, organocarbamate, organophosphorous, insect growth regulator, formamidine, chlorinated hydrocarbon, and natural insecticidal agents.
2. The synergistic combination of Claim 1 wherein the organotin compound is cyhexatin or fenbutatin oxide; the pyrethroid compound is permethrin, cypermethrin, fenvalerate or deltamethrin; the chitin synthesis inhibitor is diflubenzuron or teflubenzuron; the ovicide is hexythiazox or clofentezine; the metabolic inhibitor is piperonyl butoxide or triphenyl phosphate; the feeding stimulant is coax; the natural insecticide is
Bacillus thuringiensis; the organocarbamate compound is methomyl, dithiocarb or carbofuran; the organophosphorous compound is acephate, chlorpyrifos, phorate, diazinon, methylparathion, malathion, dimethoate; the tertiary amino is cartap; the insect growth regulator compound is diflubenzuron; the formamidine compound is amitraz or chlordimeform, and the chlorinated compound is dicofol, bromopropylate, or endosulfan wherein the compounds are present at a proportion of from 1 part of the avermectin compound to 2,500 parts of combining compound, to from 100 parts avermectin compound to 1 part of combining compound.
3. A method for the treatment of agricultural insect and mite infestations which comprises applying to an agricultural crop or commodity infected with insects or mites, the synergistic combination of Claim 1.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US22027588A | 1988-07-18 | 1988-07-18 |
Publications (2)
Publication Number | Publication Date |
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GB8915734D0 GB8915734D0 (en) | 1989-08-31 |
GB2220856A true GB2220856A (en) | 1990-01-24 |
Family
ID=22822875
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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GB8915734A Withdrawn GB2220856A (en) | 1988-07-18 | 1989-07-10 | Novel synergistic agricultural insecticidal and acaricidal combinations containing avermectin derivatives |
Country Status (2)
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JP (1) | JPH0288509A (en) |
GB (1) | GB2220856A (en) |
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GB0302309D0 (en) * | 2003-01-31 | 2003-03-05 | Syngenta Participations Ag | Avermectin monosaccharide derivatives substituted in the 4 -position having pesticidal properties |
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JPS60214715A (en) * | 1984-04-05 | 1985-10-28 | Sumitomo Chem Co Ltd | Insecticidal and acaricidal composition |
DE3602276A1 (en) * | 1986-01-25 | 1987-08-06 | Hoechst Ag | Pesticides |
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EP0089202A1 (en) * | 1982-03-16 | 1983-09-21 | Merck & Co. Inc. | 4"-Keto and-4"-amino-4"-deoxy avermectin compounds and substituted amino derivatives thereof |
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Also Published As
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GB8915734D0 (en) | 1989-08-31 |
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