Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
  • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
  • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
  • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
  • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
  • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
  • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
  • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
  • C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms

Definitions

• This invention relates to organic compounds useful as pesticides and more particularly to carbamate derivatives of ketoximes having insecticidal, mi'ticidal, and, in some cases, nematocidal activity comparable or superior to the most closely related commercial products while having significantly lower toxicity toward mam mals than these commercial products.
• Ketoxime compounds of Formulas (l) and (II) below were virtually inactive when compared with the aldoxime derivative Ketoxime compounds of Formulas (l) and (II) below are reported in the reference as being essentially inactive compared to the aldoxime compound of Formula (Ill) below which is known commercially as aldicarb (Temik).
• the compound of Formula (II) differs from the compound of Formula (Ill) only in that a methyl group has been substituted for the aldehydric hydrogen of Formula (Ill).
• R -R hydrogen, lower alkyl, lower alkenyl. lower alkynyl, substituted lower alkyl, alkenyl, or alkynyl with the proviso that R and R may be connected to form a cycloaliphatic ring;
• R R -R or X with the proviso that when R, and X are OR SR S(O)R,,, SO. ,R,,, or NR,,R,,, R and X may be connected to form a heterocyclic ring;
• R -R hydrogen, lower alkyl, lower alkenyl, or
• R hydrogen, lower alkyl, lower alkenyl, lower alkynyl, aryl, substituted aryl, carbamyl, substituted carbamyl, acyl, or substituted acyl with the proviso that the lower alkyl or alkenyyl groups may be further substituted with X;
• R hydrogen or lower alkyl with the proviso that R R and N in the NR R group may form a heterocyclic ring.
• lower alkyl radical means a radical having from one to about seven carbon atoms.
• This invention specifically includes those carbamates of Formula (IV) where R and R are lower alkyl radicals such as methyl; R is either R or X; R and R are hydrogen; X is s( )nRg Where n O, 1, or 2; R is a lower alkyyl radical such as methyl; and R and R are individually hydrogen, a lower alkyl radical such as methyl or a lower alkenyl radical.
• the oral toxicity of the compound of Formula (V), measured on albino rats and expressed as the LD was found to be 8.5 mgm/kg of body weight; the dermal toxicity, measured on albino rabbits, again expressed as the LD was 38.9 mgm/kg of body weight.
• LD is a standard means of expressing toxicity and indicates the concentration required to kill 509'! of the test animals. In each case, the LD value is approximately eight times greater than the reported value for the carbamate derivative of the aldoxime compound of Formula (III).
• a further object is to provide a method for producing these carbamates.
• Another object is to provide pesticidal compositions containing these carbamates.
• Still another object is to provide methods for combatting pests such as insects, mites, and nematodes using these carbamates. It is intended. however, that the detailed description and specific examples given herein do not limit this invention but merely indicate preferred embodiments thereof since various changes and modifications within the scope of this invention will become apparent to those skilled in the art.
• Preferred compounds of Formula (IV) include carbamate derivatives of l-hydrocarbylthio(or l-azido)-2- alkanone oximes wherein the carbamate nitrogen can be substituted with zero, one, or two lower alkyl groups; the carbon atom (C substituted by the hydrocarbylthio(or azido) group is not further substituted; and the carbon atom (C not substituted by the hydrocarbylthio-(or azido) groups is preferably substituted with an alkyl group and is optimally completely alkylated to provide a maximum degree of branching on this carbon atom.
• a second preferred group of Formula (IV) compounds include carbamate derivatives of lhydrocarbylthio(or l-azido)-2-alkanone oximes wherein the carbamate nitrogen can be substituted with zero, one, or two lower alkyl groups; the carbon atom (C substituted by the hydrocarbylthio(or azido) group is not further substituted; and the carbon atom (C is preferably substituted with a substituent of group X and is optimally further completely alkylated to provide a maximum degree of branching on this carbon atom.
• these compounds include those wherein the sulfide linkage of the above compounds is replaced by an oxide linkage, a sulfinyl linkage or a sulfonyl linkage as, for example: l-methoxy-3,3-dimethyl-2-methylcarbamyloximinobutane; l-ethoxy-3,3-dimethyl-2-methylcarbamyloximinobutane; l-(2-propenyloxy)-3,3-dimethyl-2-methylcarbamyloximinobutane; l-methoxy-3-methyl-2-methylcarbamyloximinobutane; l-ethoxy-3-methyl-2-methylcarbamyloximinobutane; l-(2-propenyloxy)-3-methyl-2-methylcarbamyloximinobutane; l-methoxy-Z-methylcarbamyloximinobutane; l-ethoxy-2-methylcarbamyloximinobutane
• X is N;;. l-azido-2-methylcarbamyloximinopropane; 1-azido-2-methylcarbamyloximinobutane; l-azido-2-methylcarbamyloximinopentane; l-azido-3-methyl-Z-methylcarbamyloximinobutane; l-azido-3-methyl-2-methylcarbamyloximinopentane; l-azido-4-methyl-2-methylcarbamyloximinopentane; l-azido-3,3-dimethyl-2-methylcarbamyloximinobutane; 1-azido-3,3-dimethyl-2-methylcarbamyloximinopentane; l-azido-3,3-dimethyl-2-methylcarbamyloximinohexane; l-azido-4,4'dimethyl-2-methylcarbamyloxi
• R is X as, for example:
• R is X as, for example:
• the carbamate nitrogen of these compounds can be unsubstituted, as in the simple carbamates, or can be substituted with a single alkyl.
• alkenyl or alkynyl substituent such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, allyl, propargyl, or the like, or can be substituted with two alkyl, alkenyl, or alkynyl groups, with the groups being the same or different, to give, for example, N,N-dimethylcarbamyloximes; N,N-diethylcarbamyloximes; N- methyl-N-ethylcarbamyloximes; N,N-di-npropylcarbamyloximes; N-methyl-N- propylcarbamyloximes; N,N-diallylcarbamyloximes; N,N,N-dimethylcarbamyloximes; N,
• ketoxime derivatives of this invention may exist in two geometric forms, the syn and the anti, representing the cis and trans isomers around the oxime double 9 10 bond. Both isomers and their mixtures are intended to dimethylaniline. Reaction is carried out from about be included in the scope of this invention. -30 C to about 100 C, preferably at from about C These compounds can be prepared by one of several to about 50 C. The resulting reaction mixture, a solumethods.
• One method involves reaction of an isocyation of the chloroformate in an inert organic solvent, nate with an oxime, as shown, for example, in the equacan be filtered or washed with water to remove amine tion: I hydrochloride before it is used in the reaction shown in RNOHR R noisyi a I t a I1 S I R I-C--( 1-X R NC0 R -C-C C-X R I R5 R3 R5 wherein R through R,; and X are as defined above.
• the Equation (2) The Equation (2).
• an amine is solvent from about 0 C to about 150 C, preferably added to the chloroformate solution in the presence of from about 20C to about 80C, and at a pressure from i an amine solvent such as water, at temperatures beabout 1 to about atmospheres, preferably from tween about 40 C and about 80 C, preferably at about 1 to about 3 atmospheres.
• Reaction pressure is about 0 C to about 40 C. A larger than molar excess determined by reaction temperature, concentration of amine can be used so that the amine acts both as reand vapor pressure of the isocyanate.
• Liquid or solid carbamates produced by the above include aliphatic and aromatic hydrocarbons, such as methods can be recovered from reaction mixtures by hexane, heptane, octane, benzene, toluene, xylene; conventional means.
• they can be recovethers such as diethyl ether, dipropyl ether, ethyl proered by removal of solvent and excess amine or isocyapyl ethere; esters such as ethyl acetate, ethyl propionate by vacuum distillation.
• esters such as ethyl acetate, ethyl propionate by vacuum distillation.
• ketones such as acetone, methyl ethyl ketone
• they can be further puchlorinated hydrocarbons such as methylene chloride, rified, if desired, by recrystallization, distillation, abperchloroethylene, and the like. sorption chromatography, or other known procedures.
• Ketoxime intermediate useful in this invention can be from about 0.1 to about 1.0% by weight, based on the prepared by well known procedures such as reaction of weight of reactants, of a tertiary amine catalyst such as the ketone with hydroxylamine in aqueous ethanol.
• a tertiary amine catalyst such as the ketone with hydroxylamine in aqueous ethanol.
• drocarbyloxy or thio ketones can be prepared by reac-
• the molar ratio of isocyanate to oxime can vary from tion of the haloketones with mercaptans or alcohols in about 0.111 to about 10:1.
• reaction times can vary pared by oxidizing the appropriate sulfide linked comfrom a few minutes to several days.
• reaction pound with sodium metaperiodate or acidic hydrogen times of from about one-half to about six hours are sufperoxide, respectively. ficient.
• the compounds of this invention can be ap- A second method for preparing these compounds inplied in undiluted form to the plant or other material volves reaction of an oxime with phosgene to obtain an being treated, it is usually desirable to apply these comoxime chloroformate which is then reacted with an pounds in admixture with either solid or liquid inert, amine.
• This method is illustrated in Equations (1) and pesticidal adjuvants.
• the compounds can (2) below: be applied to plants for pesticidal purposes by spraying 9 1 1 I YOH 13 I'M l lOCC1 R (1) R ICC !--X coc1 R2--e--c :--x
• ceptor such as a tertiary amine, e.g., N,N- toluene,xylene, kerosene,diesel oil, fuel oil, hydrocarbons, and naphthas; ketones such as acetone, methyl ethyl ketone and cyclohexanone; chlorinated hydrocarbons such as trichlorethylene, perchloroethylene; esters such as ethyl acetate, amyl acetate and butyl acetate; ethers of ethylene glycol such as the monomethyl and monoalkyl ethers of diethylene glycol, the monoethyl ether of propylene glycol; alcohols such as ethanol, isopropanol, pentanols, and the like.
• a tertiary amine e.g., N,N- toluene,xylene, kerosene,diesel oil, fuel oil, hydrocarbons, and naphth
• These compounds can also be applied to plants and other materials in conjunction with inert solid adjuvants or carriers such as talc, pyrophyllite, attapulgite, chalk, diatomaceous earth, koalinite, montmorillonite, other silicates, silica, lime, calcium carbonate, certain organic carriers such as walnut shell flour, wood flour, ground corn cobs, and the like.
• inert solid adjuvants or carriers such as talc, pyrophyllite, attapulgite, chalk, diatomaceous earth, koalinite, montmorillonite, other silicates, silica, lime, calcium carbonate, certain organic carriers such as walnut shell flour, wood flour, ground corn cobs, and the like.
• a surfactant a surface active agent
• An anionic, nonionic or cationic surfactant can be used in the formulation of either solid or liquid compositions.
• Typical surfactants include alkyl sulfonates, alkylaryl sulfonates.
• Solid and liquid formulations can be prepared by any suitable method. Solid active ingredients, in finely divided form, can be tumbled together with a finely divided solid carrier. Alternatively, the active ingredient in liquid forms such as solutions, dispersions, emulsions or suspensions, can be admixed with the solid carrier in finely divided form in amounts small enough to preserve the free-flowing property of the final dust compositions.
• the formulation be in the form of a finely divided powder or dust sufficiently fine that substantially all of the solids will pass through a Tyler sieve having a mesh size between about 20 and about 200.
• the active ingredient can be present in an amount of 5 to 50% of the total weight. However, concentrations outside this range are operative and compositions containing from 1 to 99% of active ingredient by weight are contemplated wherein the remainder is carrier and/or any other desired additive or adjuvant. It may be advantageous to add a small amount of surfactant, e.g., 0.5 to 1% by weight based on the total weight of the dust formulation.
• the active ingredient may be dissolved or dispersed in a liquid carrier, such as water or other suitable liquid.
• a liquid carrier such as water or other suitable liquid.
• the active ingredient can be added in the form of a solution, suspension, dispersion or cmulsion in aqueous or nonaqueous medium. Desirably, 0.5 to 1.0% by weight of surfactant is present in the liquid composition.
• any desired quantity of surfactant may be employed, such as up to 250% by weight of the active ingredient. If the surfactant is used only to impart wetting qualities to a spray solution, as little as 0.05% or less, by weight of the surfactant need be used. Larger quantities of surfactant are used because of biological behavior of the surfactant rather than its wetting properties. These considerations are particularly important in the treatment of plants.
• active ingredient in liquid formulations often may not be more than 30% by weight of the total and may be 10% by weight of even as low as 0.01% by weight.
• pesticidal granules include elimination of water during application, reduction of drift, penetration through vegetative coverage, easy handling, storage, and increased safety to handlers of the pesticides.
• Useful granule base materials include attapulgite, montmorillonite, corn cobs, walnut shells, and expanded vermiculites. Depending on their physical properties, the pesticides are either directly sprayed on the preformed granular base or are dissolved in a suitable solvent and then sprayed onto the granular base after which the solvent is removed by evaporation.
• Granule base materials are usually 60 to 14 US. sieve size particles, although other size particles may also be used.
• pesticide and pesticidal as used herein are intended to refer to the killing and/or control of insects, mites, nematodes, or the like. It will be appreciated that applications commonly referred to as insecticidal, miticidal, nematocidal, or the like are contemplated in the employment of these terms.
• EXAMPLE 6 1-Bromo-3,3-dimethyl-2-butanone oxime (Compound A solution of 69.5 g 1.0 m) of hydroxylamine hydrochloride in 100 ml of water is chilled in an ice bath as 90 g (0.5 m) of l-bromo-3,3-dimethyl-2-butanone is added. After addition of 100 ml of 95% ethanol, the mixture is stirred for 16 hours and allowed to warm to room temperature. The resulting white slurry is filtered, and the solid is washed with water and dried to give 55 g of the desired compound, in. 1 1 1-1 12 C.
• EXAMPLE 8 3,3-Dimethyl-2-methylcarbamyloximinol -methylsulfinylbutane (Compound 7804)
• a stirred mixture of 9.0 g (0.042 m) of sodium metaperiodate in 60 ml of water and 25 ml of methanol is cooled to 0 C as 8.7 g (0.04 m) of 3,3-dimethyl-2- methylcarbamyloximino-l-methylthiobutane is added in portions.
• the mixture is allowed to warm to room temperature and stripped of volatiles on a rotary evaporator to give a residue which is extracted with ethyl acetate. The dried extrace is stripped to leave 9 g (96%) of viscous yellow oil, the desired compound.
• This compound (7 g, 0.044 m) and 18 g (0.26 m) of hydroxylamine hydrochloride in ml of absolute ethanol containing 30 ml of pyridine are heated under reflux for 120 hours. Pouring the clear solution into ice water gives a solid which is collected and dried. This white solid, m. 128-129 C, is the desired compound, 2,Z-dimethyl-4-methylthio-3-pentanone oxime.
• EXAMPLE 1 4,4-Dimethyl-3-methylcarbamyloximino-l-methylthiopentane (Compound 81 l l)
• a solution of sodium thiomethoxide prepared from 5.8 g (0.25 gram atom) of sodium, 135 g (0.28 m) of methanethiol, and 170 ml of absolute ethanol, is treated with 36.6 g (0.25 m) of l-chloro-4,4-dimethyl- 3-pentanone at 3 to 8 C over 30 minutes. After being heated at 4045 C for 45 minutes, the mixture is filtered and distilled to give 12 g of colorless liquid, b. 73 C/2 mm, n 1.4623.
• Methylcarbamyloximinol-( l-methylcyclohexyl)-2- methylthioethane (Compound 8179) 1 Methylthioacetyl 1 -methylcyclohexane is prepared by treating a solution of sodium thiomethoxide [from 3 g (013 gram atom) of sodium, 6.7 g (0.14 m) of methanethiol, and ml of absolute ethanol] with 22.5 g (0.13 m) of l-chloroacetyl-lmethylcyclohexane over 20 minutes at 4-9 C. After being heated at 4045" C for 1 hour, the reaction mixture is filtered and distilled to give 7 g of colorless liquid, b. 8687 C/0.8 mm, n 1.4954.
• This ketone is converted to the oxime by heating a solution of5 g (0.027 m) of ketone, 3.8 g (0.054 m) of hydroxylamine hydrochloride, and 3 g (0.027 m) of anhydrous sodium carbonate in 30 ml of 95% ethanol and 26 ml of water for 95 hours. The resulting solution is stripped of volatiles, to give a two-layer liquid residue, which is extracted with ethyl acetate. The organic layer is dried, filtered, and stripped to give 3.4 g of amber liquid, n 1.5164.
• EXAMPLE l3 1-( l-Adamantyl)- 1 -methylcarbamyloximino-2- methylthioethane (Compound 8191 A solution of 4 g (0.018 m) of l-methylthioacetyladamantane, 2.5 g (0.036 m) of hydroxylamine hydrochloride, and 1.9 g (0.018 m) of anhydrous sodium carbonate in 20 m1 of 95% ethanol and 18 ml of water is heated under reflux for 29 hours. Stripping of volatiles gives a slurry which is filtered to obtain 4.2 g of white solid oxime, m. l00-l03 C.
• EXAMPLE 14 l-Chloro-4,4-dimethyl-2-methylcarbamyloximinopentane (Compound 8108) To a chilled, stirred mixture of 20.2 g (0.29 m) of hydroxylamine hydrochloride in 30 ml of water is added 21.5 g (0.145 m) of l-chloro-4,4-dimethyl-2- pentanone followed by 30 ml of 95% ethanol. The cooled mixture is stirred for six hours, allowed to stand overnight, and stripped of volatiles to obtain a residue which extracted with ethyl acetate. This extract is dried, stripped, and distilled to yield a colorless liquid, b. 76-77 C/l.3 mm, 11, 1.4672. which is the desired oxime.
• thio 2 bumnone is dried over magnesium sulfate, filtered, and stripped 7860 1-ethy1thi0-3.3-dimethyl-2-butanone c 7900 l-methylthio-Z-butanone of YOldIllfiSjO give 6.7 g (63 /c) of amber. viscous liquid 7909 lldimethYlLmethyhhioamemnone resldue, "n 7965 4,4-dimethyl-l methylthio-3-pentanone Calcd.
• the compounds are evaluated for biological activity against the following representative pests: Mexican bean bettle (Epilaclina varivestis), Southern army worm (Prodenia eridania), housefly (Musca domestica), bean aphid (Aphisfabue). and red spider mite (Terranyclms s1). The last two pests are treated both by contact and systemic application.
• Example 2 Contact Activity Systemic Activity
• the spray and systemic application methods described in Example are used to apply the test formulations to the infested plants and soil. After three days, two of the four leaves treated are examined and mortal- Bean Aphid Spray and Systemic Test This test determines the insecticidal activity of the compound being tested against the bean aphid Aphisfabae.
• Stock formulations containing 500 ppm of each test chemical are prepared using 0.05 g of the test chemical (or 0.05 ml if a liquid), 4.0 ml acetone containing 0.25% (V/V) Triton X-l55, and 96.0 ml deionized water and are used in both soil drench and spray treatments.
• the stock formulations are diluted to obtain the appropriate lower concentrations maintaining the concentration level of all adjuvants.
• the bean aphid is cultured on nasturtium plants (var. Tall Single), no attempt being made to select insects of a given age in these tests.
• Single nasturtium test plants growing in soil in individual 2% inch fiber pots are then infested with populations of 100 to 200 aphids.
• EXAMPLE 16 Red Spider Mite Sptay and Systemic Test ity is determined. Should a compound be an effective miticide, the other two leaves are available to obtain information on the residual activity of the formulation. Results of this test are shown in Table 7 as M (mite contact spray test) and MS (mite systemic soil drench test).
• EXAMPLE l7 Housefly Spray Test This test determines the insecticidal activity of the compound being tested against adult houseflies, Musca domestica. Stock formulations containing 500 ppm of each test chemical are prepared using the procedure described in Example 15 and are diluted to obtain the appropriate lower concentrations.
• Ten adult flies are placed in a cylindrical screen cage 1%. by 4 inches fabricated from 20-mesh stainless steel screening and are sprayed with 50 ml of the stock or diluted formulation.
• the flies are suplied food and drink from a dextrose solution by draping a paper wick over the outside of the screen cylinder and are able to feed and drink ad libitum.
• Percent mortality obtained is determined three days after treatment. Results of this test are shown in Table 7 as HF (housefly spray test).
• EXAMPLE is Southern Army Worm Spray Test Paired fully expanded primary leaves excited from I Scarlet runner bean plants are maintained in plastic tubes containing water and sprayed with the test formulation prepared as described in ExamplelS. After the spray deposit on the leaves is dry, the paired leaves are separated. One leaf is placed onto 1.5 percent water agar and infested with 10 newly hatched Southern army worm larvae. The covered test receptacle is held at 72.
• EXAMPLE 19 e Mexican Bean Beetle Leaf Spray'Test This test determines the insecticidal activity of the compound being tested against the Mexican bean beetle (Epilaclzna rarirestis). The test procedure is the same as that described for the Southern army worm in Example 18 with the exception that one-day old larvae of the Mexican bean beetle instead of newly hatched Southern army worm larvae are used.
• EXAMPLE 20 Systemic Test of Compound 7268 against Lygus Bug and Spotted Cucumber Beetle The techniques used are essentiallythesame for the systemic tests described above in Example-l 5.
• the test compound is Compound 7268.
• One plant is used for each test species. The checks showed no mortality during the tests.
• test organism is a strain of Southern corn rootworm (Diabrotica undecimpunctala howardi) resistant to chlorinated hydrocarbon insecticides and the test compound is Compound 7268.
• Duplicate samples of sand-soil mixtures are treated with appropriate volumes of test formulation to give the desired dosages.
• the sand-soil samples are in covered paper cups, and several hours after drenching, all cups are given a thorough shaking to-provide complete and uniform mixing of the chemical throughout the soil.
• One day after treatment two corn seedlings and five rootworms are placed into each cup and the lids replaced. Five days later, mortality is determined. The results are given below:
• test plants are cucumber seedlings; the test compound is Compound 7268; and the pest is the melon aphid (Aplzis gosyppi).
• Root-knot Nematocide Test This test is an evaluation of the effectiveness of the compound being tested against infection by root-knot nematodes (Meloidogyne spp.
• Composted greenhouse soil diluted by one-third with clean washed sand. is infested with about two grams of knotted or galled tomato roots per pot. Treatment is accomplished by applying 25 ml of the formulated compound onto the infested soil.
• the test formulation contains 0.056 g of Compound 7960, 1.0 ml stock emulsifier solution (0.25% Triton X-l55 in acetone by volume), and 24.0 ml deionized water, giving a concentration of 2240 ppm. Lower concentrations are achieved by dilution.
• R is hydrogen or lower alkyl
• b. R; R is lower alkyl with the proviso that R and R may be connected to form a cycloalkyl ring of 90 not more than 6 carbon atoms;
• R R is hydrogen, lower alkyl or lower alkenyl
• X is SR S(O)R or 50 R and,
• R is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, or aryl
• composition of matter of claim 1 selected from the group consisting of:
• composition of matter of claim 1 wherein the composition is 3,3-dimethyl-2- methylcarbamyloximino-l-methylthiobutane.
• composition of matter of claim 1 wherein the composition is 3,3-dimethyl-2- methylcarbamyloximinol-methylsulfinylbutane.
• composition of matter of claim 1 wherein the composition is 3,3-dimethyl-2- methylcarbamyloximinol -methylthiopentane.
• composition of matter of claim 1 wherein the composition is 3,3-dimethyl-2- methylcarbamyloximinol -methylsulfonylbutane.

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• 1972
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  • 1972-04-07 CH CH436875A patent/CH585194A5/xx not_active IP Right Cessation
  • 1972-04-07 DE DE2216838A patent/DE2216838C2/de not_active Expired
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• 1975
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