Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
  • C07C333/14—Dithiocarbamic acids; Derivatives thereof
  • C07C333/18—Esters of dithiocarbamic acids
  • C07C333/20—Esters of dithiocarbamic acids having nitrogen atoms of dithiocarbamate groups bound to hydrogen atoms or to acyclic carbon atoms

Definitions

• ABSTRACT Compounds having the formula in which R is alkyl having 1 to 8 carbon atoms, R is hydrogen or alkyl having 1 to 4 carbon atoms, R is hydrogen or alkyl having 1 to 4 carbon atoms, R is alkyl having I to 8 carbon atoms, X is oxygen or sulfur and X is oxygen or sulfur.
• the compounds of the present invention are believed to have the further advantages that they are non-toxic to warm blooded animals and are highly effective in controlling insects at low dosages.
• One embodiment of the present invention is concerned with novel pesticidal compositions.
• the invention is concerned with the active pesticidal component of such compositions.
• the invention is concerned with a process for controlling insects by hindering or impeding the metamorphosis and reproduction of the insects.
• the compounds of the present invention that are useful in controlling insects are those having the formula in which R is alkyl having 1 to 8 carbon atoms, preferably 2 to 6 carbon atoms; R is hydrogen or alkyl having I to 4 carbon atoms, preferably hydrogen; R is hydrogen or, preferably, alkyl having 1 to 4 carbon atoms, preferably 1 to 3 carbon atoms; R is alkyl having 1 to 8 carbon atoms, preferably 2 to 6 carbon atoms; X is' oxygen or sulfur and X is oxygen or sulfur.
• the above compounds are useful in impeding the metamorphosis and/or the reproduction of-insects.
• the activity of the compounds is such that insects at any stage of their development can be effectively treated therewith.
• the compounds of this invention can be prepared by the following reaction:
• the reaction is carried out in a solvent such as water, with stirring by slowing adding the alkyl chloro(thio)formate or mixture of alkyl chloro(thio)- formates to the diamine in the presence of an acid acceptor, such as a solution of NaOH, at a temperature around 0C. followed by stirring at room temperature to complete the exothermic reaction.
• an acid acceptor such as a solution of NaOH
• the reaction product is recovered by conventional techniques such as extracting with methylene chloride, washing the solvent phase with water, followed by drying with anhydrous MgSO Finally, the solvent is filtered and removed by vacuum stripping.
• the reaction is carried out using equal mole amounts of the reactants, although a slight excess of a reactant can be used.
• Example I v N,N-diethyl-l ,2-bis(n-propylthiocarbamoyl) ethane C2115 C2H5 2.9 grams (0.025 mole), N,N-diethyl ethylene diamine, 25 milliliters water, 4.0 grams (50 percent) NaOH solution (0.05 mole) are mixed in a 3-neck flask equipped with a dropping funnel and a mechanical stirrer and stirring in an ice bath. 6.9 grams (0.05 mole) n-propylchlorothiolformate are slowly dropped into the mixture causing a exothermic reaction. The ice bath is removed and the reaction mixture is stirred at room temperature for A hour.
• reaction product is recovered by extracting with 100 milliliters c1-nc1, and then washing it with milliliters water, followed by drying with MgSO The organic phase is filtered and stripped by yield 6.9 grams of the desired product.
• N P-1.5022. LR. and n.m.r. analysis confirm the structure.
• the degree of activity of a candidate compound to hinder or impede the metamorphosis of insects is measured by treating the penultimate larval stage of a representative insect with the compound and examining it after its last molt toward the adult form for retention of immature features.
• the compounds of this invention are generally embodied-into a form suitable for convenient application.
• the compounds can be embodied into pesticidal composition which are provided in the form of emulsions, suspensions, solutions, dusts, and aerosol sprays.
• such compositions will contain, in addition to the active compound, the adjuvants which are found normally in pesticide preparations.
• the active compounds of this invention can be employed as the sole pesticide component or they can be used in admixture with other compounds having similar utility.
• the pesticide compositions of this invention can contain, as adjuvants, organic solvents, such as sesame oil, xylene range solvents, heavy petroleum, etc., water; emulsifying agents; surface active agents; talc; pyrophyllite; diatomite; gypsum; clays; propellants, such as dichlorodifluoromethane, etc.
• organic solvents such as sesame oil, xylene range solvents, heavy petroleum, etc.
• emulsifying agents such as sesame oil, xylene range solvents, heavy petroleum, etc.
• surface active agents such as sesame oil, xylene range solvents, heavy petroleum, etc.
• talc emulsifying agents
• pyrophyllite pyrophyllite
• diatomite gypsum
• clays gypsum
• propellants such as dichlorodifluoromethane
• Thecompounds can also be combined with baits in a conventional manner.
• the active pesticide compound will be embodied in the form of a liquid composition, for example, an emulsion, suspension, or aerosol spray. While the concentration of the active pesticide in the present compositions can vary within rather wide limits, ordinarily the pesticide compound will comprise not more than about 50 percent by weight of the composition. Preferably, however, the pesticide compositions of this invention will be in the form of solutions or suspensions containing about 0.1 to 1.0 percent by weight of the active pesticide compound.
• R is alkyl having 2 to 6 carbon atoms;
• R is hydrogen or alkyl having 1 to 4 carbon atoms;
• R is alkyl having 1 to 4 carbon atoms;
• R is alkyl having 2 to 6 carbon atoms;
• X is sulfur and X is sulfur.
• R is alkyl having 2 to 6 carbon atoms
• R is hydrogen
• R is alkyl having 1 to 3 carbon atoms
• R is alkyl having 2 to 6 carbon atoms
• X is sulfur and X is sulfur.
• R is alkyl having 2 to 6 carbon atoms
• R is alkyl having 1 to 3 carbon atoms
• R is alkyl having 1 to 3 carbon atoms
• R is alkyl having 2 to 6 carbon atoms
• X is sulfur and X is sulfur.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Citations (6)

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• 1972
  • 1972-05-26 US US00257092A patent/US3846466A/en not_active Expired - Lifetime
• 1973
  • 1973-01-01 AR AR248182A patent/AR204508A1/es active
  • 1973-05-03 GB GB2097473A patent/GB1385602A/en not_active Expired
  • 1973-05-12 DE DE2324020A patent/DE2324020A1/de active Pending
  • 1973-05-22 CA CA171,963A patent/CA1010052A/en not_active Expired
  • 1973-05-22 CS CS3675A patent/CS178426B2/cs unknown
  • 1973-05-22 ZA ZA733452A patent/ZA733452B/xx unknown
  • 1973-05-22 JP JP48056430A patent/JPS4941529A/ja active Pending
  • 1973-05-23 CH CH736573A patent/CH574209A5/xx not_active IP Right Cessation
  • 1973-05-23 AU AU56042/73A patent/AU469589B2/en not_active Expired
  • 1973-05-24 FR FR7318977A patent/FR2189386B1/fr not_active Expired
  • 1973-05-24 GT GT197328916A patent/GT197328916A/es unknown
  • 1973-05-24 IT IT50192/73A patent/IT985198B/it active
  • 1973-05-25 BR BR3867/73A patent/BR7303867D0/pt unknown
  • 1973-05-25 DD DD171091A patent/DD104695A5/xx unknown
  • 1973-05-25 BE BE131536A patent/BE800053A/xx unknown
  • 1973-05-25 IL IL42356A patent/IL42356A0/xx unknown
  • 1973-05-25 NL NL7307336A patent/NL7307336A/xx unknown
  • 1973-05-26 RO RO7374927A patent/RO71925A/ro unknown

Patent Citations (6)

Non-Patent Citations (3)

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