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
  • 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
  • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles

Definitions

• This invention relates to a method of use against arthropod, plant nematode, helminth and protozoan pests implementing 2-imidazolinone derivatives.
• Fungicidal 2-imidazolinones are described in the litterature, for example in European applications EP 0511048, EP 0599749, EP 0629616, in the international application WO 94/01410. Also WO 93/24467 discloses fungicidal imidazolinones. No insecticidal properties of such compounds are disclosed in any of these publications. It is, therefore, clear that insecticidal activity is not readily apparent from the prior art.
• the present invention relates to a method for the control of pests at a locus which comprises treatment of the locus (e.g., by application or administration) with an effective amount of a compound of formula I :
• - n and p are equal to 0 or 1 ;
• - B represents N(R_t) or CH 2 ;
• - W represents O, S, SO or NR 37 wherein R 37 is here-after defined ;
• - Ri represents a hydrogen atom, or a vinyl or allyl group , or a alkyl or haloalkyl radical, with from 1 to 3 carbon atoms ;
• Rj and R 2 ⁇ being additionally able to form, with the carbon to which they are bonded to the ring, a carbocycle or a heterocycle having from 5 to 7 atoms, it being possible for these rings to be fused with a phenyl, each of these radicals being optionally substituted by 1 to 3 groups chosen from amongst the meanings of R 5 ;
• - R 3 represents an aryl or heteroaryl radical including phenyl, thienyl, naphtyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, thiazolyl, benzothienyl, benzofuryl, quinolinyl, isoquinolinyl, benzothiazolyl ou methylene dioxyphenyl, each of these radicals being optionally substituted by 1 to 7 groups, preferably 1 to 3 groups, selected among the meanings of R5 here-after defined ; - R_ ⁇ represents a hydrogen atom , a formyl or aroyl radical , an acyl radical containing 2 to 6 carbon atoms , an alkoxycarbonyl radical containing 2 to 6 carbon atoms , an aryloxycarbonyl or
• alkyl haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, cyanoalkoxy, alkylthio, haloalkylthio, cyanoalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfmyl or haloalkylsulfonyl, each containing 1 to 6 de carbon atoms ; or
• cycloalkyl halocycloalkyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio radical , each containing 3 to 6 carbon atoms ;
• -an amino radical optionally mono- or disubstimted by an alkyl or acyl radical containing 1 to 6 carbon atoms or an alkoxycarbonyl radical containing 2 to 6 carbon atoms ;
• aryl radical including phenyl, naphtyl, thienyl, furyl, pyridyl, benzothienyl, benzofuryl, quinolinyl, isoquinolyl, or methylene dioxyphenyl, optionally substituted by 1 to 3 groups selected among the meanings of R 5 or
• - Ar j represents a divalent radical derived from phenyl, thienyl, pyridyl, optionally substituted by 1 to 3 groups selected among the meanings of R 5 ;
• - Ar 2 represents a phenyl, naphtyl, pyridyl, or benzothiazolyl radical optionally substituted by 1 to 3 groups selected among the meanings of R5 ;
• R and R' represent a hydrocarbon with 1 to 3 carbon atoms , preferably a methylene group, wherein a carbon atom is optionally substituted by O or NH, and which is optionally substituted by 1 to 3 groups selected among a halogen atom , a hydroxy, oxo group or a C C 3 alkyl or C 1 -C 3 alkoxy radical ;
• RJO and R' ⁇ ⁇ are a hydrogen or halogen atom, a hydroxyl, C1-C 3 alkyl or C J -C 3 alkoxy radical :
• R11 and R' 11 are a hydrogen or chlorine atom ;
• R 37 represents R 38 , OR 39 , N(R 38 )R 40 or SO 2 R_-. ⁇ wherein :
• R 38 represents : - the hydrogen atom or the cyano group ;
• an aralkyl group optionally substituted on the aromatic portions by 1 to 3 groups selected among the meanings of R5 or optionally substituted on the aliphatic portions by R 5 ;
• N(R38)R40 can also represent a morpholino, piperidino, or piperazino group optionally substituted by an alkyl ;
• the compounds of formula (I) can be prepared according to known processes. Other ones can be prepared according to the preparation methods which are given here-after. In the general description of preparative processes the conditions given are those which will generally be used : it is to be understood that conditions other than those specified may be used, depending on, for example, the particular reactants used.
• the compounds of formula (I), wherein (Y)n represents a sufur atom and R 2 ⁇ is different from the group Ar 2 -X-Ar j and W is other than NR 37 can be prepared according to a process described in the European application EP 0551048.
• the compounds of formula (I), wherein n equals 0 and R 2 - is different from the group Ar 2 -X-Ar ⁇ and W is other than NR 37 , can be prepared according to a process described in the international application WO 94/01410.
• the 2 enantiomers of the compounds of formula (I) which correspond to the asymmetric carbon of the imidazolinone ring linked to Ri can be prepared according to one of the processes described in the European application EP 0629616.
• R 4 represents a formyl radical, an acyl group containing
• - L' represents: a halogen atom, preferably chlorine, bromine or iodine, a sulphate group, an optionally substituted aryloxy or arylthio radical, preferably phenoxy, an alkoxy or dialkylamino radical, a group R,O when R ⁇ , is an acyl or arylsulphonyl or alkylsulphonyl group.
• a strong base such as an alkali metal or alkaline-earth metal hydride or hydroxide, an alkoxide or tertiary amine.
• the reaction is carried out at a temperature of between -30°C and +50°C.
• the solvent is chosen from cyclic or non-cyclic ethers, dimethylformamide, dimethyl sulphoxide, acetonitrile or an aromatic solvent.
• L represents a group chosen from a halogen atom (preferably chlorine, bromine or iodine) or an alkyl sulphate, alkylsulphonyloxy or arylsulphonyloxy group.
• a strong base such as an alkali metal or alkaline-earth metal alkoxide (preferably potassium tert-butoxide), an alkali metal or alkaline-earth metal hydroxide, an alkali metal or alkaline-earth metal carbonate or a tertiary arnine.
• Use is made, as solvent, of a cyclic or non- cyclic ether, an alkyl ester, acetonitrile, an alcohol containing 1 to 4 carbon atoms, a chlorinated solvent or an aromatic solvent.
• Use is preferably made, as solvent, of tetrahydrofuran (THF). The reaction is carried out at a temperature of between -5°C and +80°C.
• dithiohydantoins of formula (Dla) are obtained from a compound of formula (TV) according to a process analogous to that described by T. Yamamoto et al. in J. Chem. Soc. Perkin Trans. I (1990), page 3003 to 3009, that is to sa accordin to the reaction :
• the thiazolidine-2,5-dithiones of formula (TV) are obtained from an isothiocyanate of formula (V) according to a process analogous to that described by T. Yamamoto et al. in J. Chem. Soc. Perkin Trans. I (1990), page 2459 to 2463, according to the reaction :
• the isothiocyanate of formula (V) is prepared from an amine of formula (VI), in which the substituents have the same meaning as in (V), according to one of the processes cited in Sulfur Reports (1989), Volume 8 (5), pages 327-375, i.e. according to the reaction:
• the 2-thiohydantoins of formula QHb which are compounds of formula (IH) in which W is an oxygen atom, are obtained according to the process described in European Patent Application EP 0551048 by a cyclization reaction of the isothiocyanates of formula (VII) with the hydrazines of formula
• R E represents a C,-C 3 alkyl radical.
• the cyclization can be carried out according to 2 embodiments. According to the first, the mixture of the reactants is heated at a temperature of between 110°C and 180°C in an aromatic solvent such as toluene, xylene, chlorobenzenes or nitrobenzene.
• the reaction is carried out in the presence of a strong base such as an alkali metal or alkaline- earth metal alkoxide, an alkali metal or alkaline-earth metal hydroxide or a tertiary amine at a temperature of between -10 and +80°C and in a solvent chosen especially from an ether, a cyclic ether, an alcohol, an ester, DMF or DMSO.
• a strong base such as an alkali metal or alkaline- earth metal alkoxide, an alkali metal or alkaline-earth metal hydroxide or a tertiary amine at a temperature of between -10 and +80°C and in a solvent chosen especially from an ether, a cyclic ether, an alcohol, an ester, DMF or DMSO.
• the ⁇ -isothiocyanato esters of formula (VE) are prepared from the ⁇ - amino acid esters of formula (VHI), in which the groups indicated have the same meaning as in the formula (VII), according to one of the processes cited in Sulfur Reports (1989), Volume 8 (5), pages 327-375, i.e. according to the reaction :
• the ⁇ -amino esters of formula (VIII) are obtained by esterifying the ⁇ - amino acids of formula (TX), in which the groups indicated have the same meaning as in the formula (V ⁇ l), with an alcohol of formula R E OH in the presence of thionyl chloride, which process is described in the literature by: M. Brenner and W. Huber: Helv. (1953), Volume 36, page 1109, according to the scheme :
• the ⁇ -amino esters of formula (VTUb) are obtained by oxidation of the ⁇ -amino esters of formula (Villa) according to processes described in Advanced Organic Chemistry, J. March (1985), page 1089 and 1090, 3rd Edition and according to the scheme :
• n is equal to 1 or 2 and R E has the meaning indicated in me definition of the formula (VII).
• ⁇ -amino acids of formula (IX) are obtained by hydrolysis of the corresponding hydantoins (X) in acidic or basic medium according to a process analogous to that described in Dutch Patent NE 69 00349 or in J. Org. Chem. (1985), Volume 50, pages 1876 to 1878, i.e. according to the scheme :
• hydantoins of formula (XL) are obtained by a B ⁇ cherer-Berg reaction on the co ⁇ esponding acetophenones, which process is described in the literature: Chem. Rev. (1950), Volume 46, pages 422-425 or Chem. Pharm.
• Process B The compounds of formula (II) in which W represents an oxygen, in other words the compounds of formula (Ha), can also be prepared by successively reacting the compound of formula (VE) with a hydrazine of formula R 3 -NH-NH 2 , then with a base of formula B " M + and finally with an alkylating agent of formula R 2 L, in which L is defined as above.
• the base is chosen from an alkali metal or alkaline-earth metal alkoxide, an alkali metal or alkaline-earth metal hydroxide or a tertiary amine.
• the reaction is carried out at a temperature of between -10 and +80°C and in a solvent chosen especially from a cyclic or non-cyclic ether, an alcohol, an ester, DMF, DMSO, acetonitrile or from an aromatic.
• the scheme of the reaction is the following :
• Process C These compounds are obtained by reacting the 2-alkylthio-2-imidazolin-
• R' 2 represents an alkyl group comprising from 1 to 3 carbon atoms.
• R' 2 represents an alkyl group comprising from 1 to 3 carbon atoms.
• R' 2 represents an alkyl group comprising from 1 to 3 carbon atoms.
• R' 2 represents an alkyl group comprising from 1 to 3 carbon atoms.
• R' 2 represents an alkyl group comprising from 1 to 3 carbon atoms.
• R 2 O " M + an alkali metal alkoxide
• R 2 O " Na + alkali metal hydroxide
• the reaction is preferably carried out in the alcohol R 2 OH, as solvent, and by using the corresponding sodium alkoxide R 2 O " Na + as base.
• the reaction is carried out at a temperature of between 20 and 80°C.
• the reaction is carried out in the presence of an oxidizing agent.
• the reaction is carried out by heating the mixture of the reactants in acetic acid at reflux, optionally in the presence of sodium acetate as catalyst.
• the azalactones of formula (XIII) are obtained by reacting the ⁇ -amino acids of formula (DC) with a carboxylic acid anhydride according to a process described in the literamre: R. Cotton et al., Int. J. Peptide Protein Res. (1986), Volume 28, pages 230 to 244 and according to the scheme:
• Process E The compounds of formula (lb) can be prepared by S-alkylation of the
• the compound of formula (XTV) can be prepared from a compound of formula (XV) using a process analog to the one described by H. CARRINGTON, J. Chem. Soc, 1947, p. 684, according to the scheme :
• L" represents a halogen atom (such as CI or Br), or a R 37 C(O)O group.
• L represents a halogen atom (such as CI or Br), or a R 37 C(O)O group.
• Use is made, as base, of a strong base such as an alkali metal or alkaline- earth metal alkoxide (preferably potassium tert-butoxide), an alkali metal or alkaline-earth metal hydroxide, an alkali metal or alkaline-earth metal carbonate or a tertiary amine.
• Use is made, as solvent, of a cyclic or non-cyclic ether, an alkyl ester, acetonitrile, an alcohol containing 1 to 4 carbon atoms, a chlorinated solvent or an aromatic solvent.
• Use is preferably made, as solvent, of toluen. The reaction is carried out at a temperature of between -5°C and +80°C.
• - W represents O, S or NR 37 ;
• - Ri represents a hydrogen atom or a alkyl radical, with from 1 to 3 carbon atoms ;
• R 3 represents an aryl or heteroaryl radical including phenyl, or pyridyl, each of these radicals being optionally substituted by 1 to 7 groups, preferably 1 to 3 groups, selected among the meanings of R 5 ;
• R 4 represents a hydrogen atom or a formyl group:
• halogen atom nitro, SF 5 , cyano or azido group ; or -an alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkylthio, cyanoalkylthio, alkylsulfinyl, alkylsulfonyl. each containing 1 to 6 carbon atoms ; or - R 2 ⁇ represents :
• Arj represents a divalent radical derived from phenyl, thienyl, pyridyl, optionally substituted by 1 to 3 groups selected among the meanings of R 5 ;
• Ar 2 represents a phenyl or pyridyl, optionally substituted by 1 to 3 groups selected among the meanings of R5;
• R and R' represent a hydrocarbon with 1 to 3 carbon atoms , preferably a methylene group
• - A is O, S, SO, SO 2 , CO;
• R 38 represents :
• - W represents O, S;
• - Ri represents a hydrogen atom, or a alkyl radical, with from 1 to 3 carbon atoms ;
• R 3 represents an aryl or heteroaryl radical including phenyl or pyridyl, each of these radicals being optionally substituted by 1 to 7 groups, preferably 1 to 3 groups, selected among the meanings of R 5 here-after defined;
• - R represents a hydrogen atom or a formyl group
• - R 5 represents:
• - Ri represents a methyl group
• - R 3 represents a phenyl group, optionally substituted by 1 to 7 groups, preferably 1 to 3 groups, selected among the meanings of R 5 ;
• - R 4 represents a hydrogen atom or a formyl group ;
• halogen atom or -a haloalkyl or alkoxy, each containing 1 to 6 carbon atoms;
• R 21 represents 2,4- or 2,5-difluorophenyl.
• - W represents O or S
• - Ri represents a methyl group
• - R represents a methyl group
• - R 3 represents a phenyl group, optionally substituted by 1 to 3 groups selected among the meanings of R 5 here-after defined at the 3, 4, or 5 positon of the phenyl ring;
• R 4 represents a hydrogen atom or a formyl group
• R 5 represents a halogen atom; or an alkoxy group containing 1 to 6 carbon atoms;
• R 2 ⁇ is 2-fluorophenyl or 2,5-difluoro-4-chlorophenyl.
• a feature of the present invention therefore provides a method of control of pests at a locus which comprises the treatment of the locus (e.g., by application or administration) with an effective amount of a compound of formula I, wherein the substituent groups are as hereinbefore defined.
• the locus includes, for example, the pest itself or the place (plant, animal, person, field, structure, premises, forest, orchard, waterway, soil, plant or animal product, or the like) where the pest resides or feeds.
• the compounds of this invention are useful in the control via foliar application or systemic action of some arthropods, especially some insects, which feed on the above ground portions of plants.
• Control of foliar pests may additionally be provided by application to the plant roots or plant seeds with subsequent systemic translocation to the above ground portions of the plants.
• the compounds of this invention may be useful to control soil insects, such as corn rootworm, termites (especially for protection of strucmres), root maggots, wireworms, root weevils, stalkborers, cutworms, root aphids, or grubs.
• the compounds may also be used to provide activity against plant pathogenic nematodes, such as root-knot, cyst, dagger, lesion, or stem or bulb nematodes, or against mites.
• plant pathogenic nematodes such as root-knot, cyst, dagger, lesion, or stem or bulb nematodes, or against mites.
• the compounds are advantageously applied to or incorporated at an effective rate into the soil in which crops are planted or to be planted or to the seeds or growing plant roots.
• the compounds are especially useful in the control of many insects, especially filth flies or other Dipteran pests, such as houseflies, stableflies, soldierflies, hornflies, deerflies, horseflies, midges, punkies, blackflies, or mosquitoes.
• Compounds of the invention may be used in the following applications and on the following pests including arthropods, especially insects or mites, nematodes, or helminth or protozoan pests:
• the invention provides methods of control of pests via application or administration of an effective amount of compounds of formula I at a locus which comprises treatment of the locus.
• a method for example, comprises applying to the plants or to the medium in which they grow an effective amount of a compound of the invention.
• the active compound is generally applied to the locus in which the arthropod or nematode infestation is to be controlled at an effective rate in the range of about 0.005 kg to about 15 kg of the active compound per hectare of locus treated. Under ideal conditions, depending on the pest to be controlled, a lower rate may offer adequate protection.
• an effective rate range of the active compound is from about 0.01 kg/ha to about 2 kg/ha.
• the active compound When a pest is soil-borne, the active compound generally in a formulated composition, is distributed evenly over the area to be treated (i.e., for example broadcast or band treatment) in any convenient manner. Application may be made, if desired, to the field or crop-growing area generally or in close proximity to the seed or plant to be protected from attack.
• the active component can be washed into the soil by spraying with water over the area or can be left to the natural action of rainfall.
• the formulated compound can, if desired, be distributed mechanically in the soil, for example by ploughing, disking, or use of drag chains. Application can be prior to planting, at planting, after planting but before sprouting has taken place, or after sprouting.
• a method of control may also comprise treatment of the seed prior to planting with subsequent control effected after planting the seed.
• Methods of control of pests also consist of application to or treatment of the foliage of plants to control arthropods, especially insects or mites, or nematodes attacking the aerial parts of the plants.
• methods of control of pests by the invention compounds are provided to control pests which feed on parts of the plant remote from the point of application, e.g., leaf feeding insects which are controlled via systemic action of the active compound when applied for example to the roots of a plant or to the plant seed prior to planting.
• the compounds of the invention may reduce attacks on a plant by means of antifeeding or repellent effects.
• the compounds of the invention and methods of control of pests therewith are of particular value in the protection of field, forage, plantation, glasshouse, orchard or vineyard crops, of ornamentals, or of plantation or forest trees, for example: cereals (such as maize, wheat, rice, or sorghum), cotton, tobacco, vegetables (such as beans, cole crops, curcurbits, lettuce, onions, tomatoes or peppers), field crops (such as potatoes, sugar beets, ground nuts, soybeans, or oil seed rape), sugar cane, grassland or forage crops (such as maize, sorghum, or lucerne), plantations (such as tea, coffee, cocoa, banana, palm oil, coconut, rubber, or spices), orchards or groves (such as of stone or pit fruit, citrus, kiwifruit, avocado, mango, olives or walnuts), vineyards, ornamental plants, flowers or vegetables or shrubs under glass or in gardens or parks, or forest trees (both deciduous and evergreen) in forests, plantations or nurseries
• stored products such as grains, fruits, nuts, spices or tobacco, whether whole, milled or compounded into products, from moth, beetle, mite or grain weevil attack.
• stored animal products such as skins, hair, wool or feathers in natural or converted form (e.g. as carpets or textiles) from moth or beetle attack as well as stored meat, fish or grains from beetle, mite or fly attack.
• the compounds of the invention and methods of use thereof are of particular value in the control of arthropods, helminths or protozoa which are injurious to, or spread or act as vectors of diseases in man and domestic animals, for example those hereinbefore mentioned, and more especially in the control of ticks, mites, lice, fleas, midges, or biting, nuisance or myiasis flies.
• the compounds of the invention are particularly useful in controlling arthropods, helminths or protozoa which are present inside domestic host animals or which feed in or on the skin or suck the blood of die animal, for which purpose they may be administered orally, parenterally, percutaneously or topically.
• Heliot is virescens tobacco budworm Musca domestica house fly Epilac na varivestis Mexican bean beetle Periplaneta americana American cockroach Diahrotica undecimpunctata southern com rootworm Agrotis ipsilon black cutworm Meloidogyne incognita southern root-knot nematode
• test compounds were formulated for use according to the following methods.
• a solution or suspension was prepared by adding the test compound to a solution of dimethylformamide, acetone, emulsifiers which are alkylaryl polyether alcohols organic sulfonates, and water. The result was a 500 ppm concentration of the test compound.
• the water-acetone-DMF-emulsifier solution was adjusted with a 20% by weight aqueous solution of sucrose to provide a 250 or 500 ppm concentration of the test compound.
• the water-acetone-DMF-emulsifier solution was adjusted for a treatment rate of 10.0 ppm soil concentration.
• the water- acetone-DMF-emulsifier solution was adjusted for a treatment rate of 6.75 ppm.
• the water-acetone-DMF- emulsifier solution was adjusted for a treatment rate of 21 or 23 kg/ha soil concentration.
• test compounds were then evaluated for their pesticidal activity at specified concentrations, in ppm (parts per million) by weight or in kg/ha (kilograms per hectare). The following procedures were used to evaluate a number of compounds within the scope of the invention.
• Twospotted spider mite A sufficient number of two-spotted spider mites (150-200) for testing were transferred to the fresh bean leaves within a period of twenty-four hours. The infested leaves were wet to runoff with the 500 ppm test compound formulation. As an untreated control, the water- acetone-DMF-emulsifier solution containing no test compound was also applied wet to runoff to infested leaves. The treated leaves were held for three or six days, after which a mortality count of motile forms was made.
• Twospotted spider mite Females were allowed to oviposit on bean plants for a period of about 24 hours, after which the leaves of the plant were dipped into a solution of TEPP (tetraethyl pyrophosphate) in order to kill the motile forms and prevent additional egg laying. This dipping procedure did not affect the viability of the eggs.
• the infested leaves were wet to runoff with the 500 ppm test compound formulation.
• a water-acetone-DMF-emulsifier solution containing no test compound was also wet to runoff on infested leaves. The treated leaves were held for seven days, after which a mortality count of egg forms was made along with notations on residual activity on hatched larvae.
• Buckthorn or cotton aphid Adult and nymphal stages of buckthorn or cotton aphid were reared on potted dwarf nasturtium or cotton plants, respectively. Plants infested with 100-150 aphids were wet to runoff with the 500 ppm test compound formulation. As an untreated control, a water-acetone- DMF-emulsifier solution containing no test compound was also applied wet to runoff to infested plants. The treated plants were stored for one day for buckthorn aphid and three days for cotton aphid, after which the dead aphids were counted.
• Cotton aphid - systemic test Cotton seeds were placed on top of the soil surface in pots containing moist soil. The test compound solution was applied as a drench to the top of the soil and seeds for a treatment rate equilvalent to 10.0 ppm soil concentration. As an untreated control, an aliquot of a water-acetone-DMF-emulsifier solution containing no test compound was applied in a similar manner. The soil surface and seeds were covered with moist soil. The pots were held in the greenhouse for the duration of the bioassay. When the cotyledons of the cotton were expanded (approximately 7 days after planting), the cotton was infested with approximately 25 cotton aphids (mixed population). The plants were rated for aphid control three and six days after infestation.
• Southern armyworm Mexican bean beetle : Bean leaves were wet to runoff with the 500 ppm test compound formulation. As an untreated control, a water-acetone-DMF-emulsifier solution containing no test compound was also applied wet to runoff to bean leaves. Five or six randomly selected second instar southern armyworm larvae or Mexican bean beetle larvae were introduced into each plastic container with the dry treated leaves. The container was closed and held for five days. Larvae which were unable to move the length of the body, even upon stimulation by prodding, were considered dead.
• Tobacco budworm Cotton leaves were wet to runoff with the 100 ppm test compound formulation. As an untreated control, a water-acetone-DMF- emulsifier solution containing no test compound was also applied wet to runoff to cotton leaves. Ten randomly selected second instar tobacco budworm larvae were introduced into plastic containers in which moist dental wicks and the dry treated leaves had been placed. The cups were closed and held for five days. Larvae which were unable to move the length of the body, even upon stimulation by prodding, were considered dead.
• House fly Four to six day old adult house flies were used. The flies were immobilized by anesthetizing with carbon dioxide. A bait cup was prepared which contained the 250 or 500 ppm test compound formulation / sucrose solution and one or two absorbent cotton pad(s). As an untreated control, a water-acetone-DMF-emulsifier-sucrose solution containing no test compound was applied in a similar manner. The bait cup was introduced inside the cage prior to admitting 12 - 25 anesthetized flies. Mortality was assessed after 24 hours.
• Southern root-knot nematode Eggs and second stage juveniles (J2s) of southern root-knot nematodes were obtained from infected roots of reared tomato plants. Pots containing moist soil were treated with the test compound solution for a treatment rate of 21 or 23 kg/ha. As an untreated control, an aliquot of a water-acetone-DMF-emulsifier solution containing no test compound was applied in a similar manner. Immediately after treatment, eggs or J2s of southern root-knot nematode were added to the treated soil. For tests with cotton, the seeds were placed on top of the seed the day of treatment and inoculation. For the tests with tomato, the seedling(s) were transplanted in the pot three days after treatment.
• the pots were kept in the greenhouse for 2-3 weeks.
• roots of the tomato or cotton seedling were evaluated for galling on a rating scale from 1 to 5 with one equal to severe galling, relative to untreated control, and five to no galling, i.e., complete control.
• Southern com rootworm Black cutworm : Com seeds were placed in a glass jar and covered with dry sandy loam soil. The 500 ppm test compound was applied for a soil concentration of 6.75 ppm. As an untreated control, an aliquot of a water-acetone-DMF-emulsifier solution containing no test compound was applied in a similar manner. After incubating covered for 24 hours, the soil was mixed and inoculated with approximately 25 southern com rootworm eggs. Following an additional 48 hours, two late second to early third instar black cutworms were placed in the jar with a portion of insect diet. Eight days after infestation, mortality was assessed visually for cutworm and by
• Black cutworm - systemic test Com seeds were placed on top of the soil surface in pots containing moist soil. The test compound solution was applied as a drench to the top of the soil and seeds for a treatment rate equilvalent to 10.0 ppm soil concentration. As an untreated control, an aliquot of a water-acetone-DMF-emulsifier solution containing no test compound was applied in a similar manner. The soil surface and seeds were covered with moist soil. The pots were held in the greenhouse for the duration of the bioassay. Ten days after treatment, the com seedling was clipped and placed in a plastic cup with 2 late second to early third instar black cutworm larvae. Mortality was assessed visually 4 days after infestation.
• - (B)p represents the N(R4) group in which 1 ⁇ is a hydrogen, a formyl or an aetyl group ;
• R j and R 2 represent a methyl
• R 2j represents a phenyl substituted on the 2-; 2,4-; or 2,5 positions by one or two halogen atoms which may be identical or different ;
• R3 represents a phenyl substituted on the 2-; 2,4-; or 2,5 positions by one or two halogen atoms which may be identical or different ;
• a methylenedioxyphenyl compound (B) selected from the group consisting of : alpha- (2-2(2-butoxyethoxy) ethoxy- 4,5- methylenedioxy-2-propyltoluene (common name : piperonyl butoxide) ; piperonal bis- (2-(2-butoxyethoxy) ethyl) acetal (common name : piprotal) ; 2-(2- ethoxyethoxy) ethyl- 3,4- (methylenedioxy)phenyl acetal of acetaldehyde (common name : sesamex) ; and 1.2- methylenedioxy-4-(2- (octylsulfmyl) propyl) benzene (common name : sulfoxide).
• the synergistic insecticidal composition according to the instant invention is particularly valuable because of its good efficiency.
• the weight ratio of A/B in the synergistic insecticidal composition according to the invention is generally between 1 : 0.05 to 1 : 3000 parts by weight, respectively, preferably between 1 :1 to 1 : 1000.
• the synergistic insecticidal composition according to the invention is effective against a wide variety of pests. It is understood that the insects evaluated in the working examples herein are representative of a wider variety of insects which can be controlled by the synergistic insecticidal composition of this invention. This composition is particularly useful in controlling insects of agricultural crops, e.g., potatoes, maize, cotton, rice, tobacco, wheat, soybeans, deciduous and citrus fruits.
• agricultural crops e.g., potatoes, maize, cotton, rice, tobacco, wheat, soybeans, deciduous and citrus fruits.
• EXAMPLE 2 effect of piperonyl butoxide on the insecticidal activity of 4-(2,4- Difluoropheny l)-4-methyl-2-methoxy- 1 -N-(Phenyl-amino)-2-imidazolin-5-one to four insects :
• a further embodiment of the present invention includes a composition comprising as active ingredient anyone of the compounds wich have been previously defined in the method according to the invention, when these compounds are used for insecticidal purpose.

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• Environmental Sciences (AREA)
• Plural Heterocyclic Compounds (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

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• 1995
  • 1995-03-03 AU AU18924/95A patent/AU1892495A/en not_active Abandoned
  • 1995-03-03 WO PCT/EP1995/000782 patent/WO1995024125A1/en active Application Filing
  • 1995-03-07 IL IL11290495A patent/IL112904A0/xx unknown
  • 1995-03-08 ZA ZA951922A patent/ZA951922B/xx unknown
  • 1995-03-09 CO CO95009161A patent/CO4410280A1/es unknown
  • 1995-03-09 TR TR00251/95A patent/TR28660A/xx unknown

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