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United States Patent (19) 11 3,976,769 Hennart (45) Aug

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United States Patent (19) 11 3,976,769 Hennart (45) Aug United States Patent (19) 11 3,976,769 Hennart (45) Aug. 24, 1976 54). PESTICIDAL COMPOSITIONS CONTAINING PHOSPHORCESTERS AND Primary Examiner-V. D. Turner DVALENT SULPHUR COMPOUNDS Attorney, Agent, or Firm-Wenderoth, Lind & Ponack 75 Inventor: Claude Hennart, Aubervilliers, France (57) ABSTRACT Pesticidal composition comprising: a pesticidal, phos 73) Assignee: Airwick Industries, Inc., Carlstadt, phoric ester the molecule of which has at least one N.J. alkyl group of 1 to 3 carbon atoms, 0.05 to 10% of an 22 Filed: Mar. 14, 1974 agent stabilizing the said ester against decomposition by protonisation, together with adjuvants character (21) Appl. No.: 451,381 ized in that the stabilizing agent comprises at least one Related U.S. Application Data sulphur compound containing per molecule at least one divalent sulphur atom of which one valence is (62) Division of Ser. No. 180,137, Sept. 13, 1971, Pat. bonded to an atom chosen from sulphur, carbon, ni No. 3,836,643. trogen, hydrogen, and metals capable of giving a salt, (30) Foreign Application Priority Data the other valence being bonded to an atom chosen from hydrogen, the carbon atom already noted, a sec Sept. 1 i, 1970 France .............................. 70.3304 ond carbon atom, the nitrogen atom already noted, a second nitrogen atom, the metal atom already noted 52) U.S. Cl................................... 424/175; 424/19; in the case of a metal of valence greater than one, a 424/32; 424/219 second atom of metal and oxygen when the first va I51l Int. Cl'............................................ A01N 9/36 lence is not attached to an atom of hydrogen, the pro 58) Field of Search............... 424/19, 27, 219, 175 portion of sulphur calculated with reference to the weight of the sulphur compound being between 5 and (56) References Cited 99%. Process for stabilizing a phosphoric ester of UNITED STATES PATENTS which the molecule possesses at least one alkyl group 3,093,536 6/1963 Loeffler.............................. 424/219 containing 1 to 3 carbon atoms characterized in that 3,097,128 7/1963 Sprinkle et al ... 424/219 there is added to the phosphoric ester or to a mixture 3, l l 6,201 12/1963 Whetstone.......................... 424/219 which contains it, 0.05 to 10% calculated on the FOREIGN PATENTS OR APPLICATIONS weight of the phosphoric acid ester of an agent capa ble of stabilizing the said phosphoric ester against 261,923 5/1974 United Kingdom protonisation and comprising at least one sulphur OTHER PUBLICATIONS compound such as that defined thereupon. Chemical Abstracts, vol. 56, (1962), p. 10635(b). Chemical Abstracts, vol. 53, (1959), p. 11743c. 7 Claims, No Drawings 3,976,769 2 C. 0 to 90%, calculated on the weight of the composi tion, one of more solvents for the phosphoric ester, PESTICIDAL COMPOSITIONS CONTAINING liquid or solid under pressure or otherwise, and PHOSPHORCESTERS AND DIVALENT SULPHUR D.. O to 50%, calculated on the weight of the composi COMPOUNDS tion of one or more inert adjuvants chosen from mineral adjuvants and organic adjuvants compati This is a division of application Ser. No. 180,137, ble with the phosphoric ester, filed Sept. 13, 1971, now U.S. Pat. No. 3,836,643. said composition being characterised in that the stabi This invention concerns a process for stabilising pes lising agent comprises at least one sulphur compound ticidal phosphoric esters, and compositions based on O containing per molecule at least one divalant Sulphur phosphoric esters so stabilised. atom of which one valence is bonded to an atom Phosphoric esters are nowadays very widespread for chosen from sulphur, carbon, nitrogen, hydrogen, and pesticidal use, particularly for insecticides. Their value a metal capable of giving a salt, the other valence being is due principally to speed of action and the absence of bonded to an atom chosen from hydrogen, the carbon accumulation of these compounds in living tissue as a 15 atom already noted, a second carbon atom, the nitro result of their rapid hydrolysis in situ. gen atom already noted, a second nitrogen atom, the This latter characteristic which gives them a net ad metal atom already noted in the case of a metal of vantage over the so called chlorinated pesticides, pre valence greater than one, a second atom of metal and sents however a very grave inconvenience; the sensitiv oxygen when the first valence is not attached to an ity of certain phosphoric esters to humidity, even sim 20 atom of hydrogen, the proportion of sulphur of sulphur ply that of the atmosphere, is such that their decompo calculated with reference to the weight of the sulphur sition takes place without their being able to act on the compound being between 5 and 99%. pest organisms: the phosphoric esters which are sensi The present invention also includes a process for tive are more particularly those which contain one or stabilising a phosphoric ester of which the molecule more low alkyl groups, such as methyl, ethyl, propyl or 25 possesses at least one alkyl group containing 1-3 car isopropyl groups attached to the phosphoric anion; this bon atoms in admixture with 0.05 to 10% calculated on produces, on contact with molecules of water, an at the weight of the phosphoric ester, of an agent stabilis least partial decomposition of these esters by protonisa ing the said ester against decomposition by protonisa tion, i.e. by displacement of one low alkyl group in tion, 0 to 90%, calculated on the weight of the compo favour of a hydrogen atom. 30 sition, of one or more solvents for the phosphoric ester Among the sensitive phosphoric esters special men which are solid or liquid under pressure or otherwise tion should be made of O-2,2-dichlorovinyl-O,O-dime and 0 to 50%, calculated on the weight of the composi thylphosphate, better known under the common name tion, of one or more inert adjuvants selected from min DICHLORVOS and the abbreviation DDVP, the use of eral adjuvants and organic adjuvants compatible with which in permanent insecticidal devices knon as evapo 35 the phosphoric ester, the said process being character rators has undergone a tremendous increase in recent ised in that there is added to the phosphoric ester or to years. a mixture which contains it, 0.05 to 10% calculated on Various means of stabilisation have already been the weight of the phosphoric acid ester of an agent suggested for limiting the decomposition of these phos capable of stabilising said phosphoric ester against phoric esters but they are generally toxic, for example 40 protonisation and comprising at least one sulphur com phenols, amines and low nitrogen heterocycles, an pound such as that defined above. The quantities of stabilising agent used according to other useful class of stabiliser comprises azoic and the present invention are preferably between 0.05 and hydrozonic compounds but these have a strong colou 4% based on the weight of the phosphoric ester. ration power so that they cannot always be used. The 45 In the sulphur compounds such as those defined ac use of anhydrides or epoxides has also been used but it cording to the invention the valences of the atom of is known that these compounds act by fixation, either sulphur which are bonded to another atom or to other of a molecule of water or a molecule of free acid; it can atoms in a molecule of the sulphur compound accord be seen that this process is limited stoichiometrically ing to the invention can be constituted by a homopolar and that the stabilisation ceases when all the stabiliser 50 bond resulting from the displacement from a telectron has entered into reaction; this leads to the necessity of doublet, by one or two heteropolar bonds resulting using substantial proportions of these stabilisers which from an exchange of electrons between the sulphur and is not economic. the atom to which it is bonded or by one or two elec The present invention has as its object the stabilisa trovalences resulting from electrostatic attraction be tion of pesticidal phosphoric esters by using substances 55 tween two ions of apposite polarity. more efficacious than those noted above and which do The sulphur compounds preferred for use in the pre not possess the inconveniences: these substances are sulphur compounds; they are suitable in particular at sent invention are as follows: relatively low concentrations for preserving phosphoric 1. Sulfanes defined by formula I esters against protonisation. Thus the invention com 60 H - (S) - H (I) prises pesticidal compositions comprising: A. 5 to 99.95%, calculated on the weight of the com in which n is a whole number between 1 and 6; such position, of a pesticidal, phosphoric ester the mole compounds are for example: cule of which has at least one alkyl group of 1-3 hydrogen monosulfide carbon atoms, 65 hydrogen bisulfide B. 0.05 to 10%, calculated on the weight of the phos hydrogen trisulfide phoric ester, of an agent stabilising said ester hydrogen tetrasulfide against decomposition by protonisation, hydrogen pentasulfide 3,976,769 3 hydrogen hexasulfide (sulphur content 98.9% by butanethiol weight) dodecanethiol 2. Mercaptans defined by formula II 1,10-decanedithiol 1,12-dodecanedithiol H - S - R (I) 5 benzylmercaptan 1,2-butanedithiol in which R is chosen from 1,4-butanedithiol i. a group Rachosen from: 4-tertiobutylbenzenethiol a. a phenyl group, 1,3-benzenedithiol b. a benzyl group, 10 4-chlorobenzenethiol c. a phenyl group and a benzyl group bearing 1-3 3,4-toluenedithiol substituents chosen from alkyl residues containing 4,5-diphenyl-2-imidazolethiol 1-6 atoms of carbon, ethyl-2-mercapto acetate d. an alkyl group containing 1-18 carbon atoms, methyl-3-mercapto propionate e, a heterocyclic group chosen from monocyclic and 15 2-mercapto benzoic acid bicyclic heterocyclic groups comprising 5 to 10 3-amino-5-mercapto-1,2,4-triazole ring atoms in one or two fused rings, the first ring 2-amino benzenethiol containing 1-3 ring members chosen from nitro 2-N-decylamino ethanethiol gen, the group 2-quinoleinethiol 20 2-mercapto benzoxazole ..
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