US3855362A - Phosphoric acid phenylsulphonamide esters - Google Patents

Phosphoric acid phenylsulphonamide esters Download PDF

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Publication number
US3855362A
US3855362A US00310507A US31050772A US3855362A US 3855362 A US3855362 A US 3855362A US 00310507 A US00310507 A US 00310507A US 31050772 A US31050772 A US 31050772A US 3855362 A US3855362 A US 3855362A
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United States
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carbon atoms
formula
parts
alkyl
methyl
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Expired - Lifetime
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US00310507A
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English (en)
Inventor
J Drabek
D Varsanyi
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Novartis Corp
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Ciba Geigy Corp
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Publication date
Priority claimed from CH1761971A external-priority patent/CH564908A5/de
Priority claimed from CH1386972A external-priority patent/CH575211A5/de
Application filed by Ciba Geigy Corp filed Critical Ciba Geigy Corp
Priority to US05/508,592 priority Critical patent/US3934010A/en
Application granted granted Critical
Publication of US3855362A publication Critical patent/US3855362A/en
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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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds

Definitions

  • the present invention relates to phosphoric acid phenylsulphonamide esters, a process for their manufacture and their use in pest control.
  • R represents oxygen or sulphur
  • R represents 7 alkyl with l to 5 carbon atoms
  • R represents alkyl with l to 5 carbon atoms
  • alkenyl and alkinyl each with 3 to 5 carbon atoms
  • alkoxyalkyl with 1 to 5 carbon atoms in each of the moieties alkylthioalkyl with l to 5 carbon atoms in each of the moieties, or haloalkyl with l to 5 carbon atoms
  • R represents hydrogen, alkyl with l to 5 carbon atoms or alkenyl with 3 to 5 carbon atoms
  • R represents hydrogen and X and X, each represents halogen or alkyl with l to 5 carbon atoms
  • R represents alkyl with l to 5 carbon atoms and X and Y R u j 1) P-Cl v H .R s j I (II) (III) Y R u P-Cl (II) (IV)
  • Halogen is to be understood as meaning fluorine
  • haloalkyl groups with l to 5 carbon atoms
  • the groups cited hereinabove which are possible for .R to R X and X, may be straight-chain or branched.
  • Examples of such groups include: methyl, methoxy, methoxymethyl, ethyl, ethoxyethyl, ethylthioethyl, propyl, isopropyl, n-, i-, sec. and tert.butyl, n-pentyl and the isomers thereof, allyl, methallyl, n-penten-S-yl, propargyl, isobutinyl.
  • Preferred compounds on account of their action are those of the formula l, wherein R represents methyl or ethyl, R, represents propyl, n-butyl, n-pentyl or C H OCH CH R represents hydrogen, methyl or ethyl, R represents methyl or ethyl, X and X, each represents hydrogen or chlorine, and Y represents oxygen or sulphur.
  • R and R each represents methylor ethyl
  • X and X represent hydrogen or chlorine and Y represents oxygen.
  • the compounds of the formula I can be manufactured according to methods'which are known per se:
  • reaction temperature 0-12O C MeSH reaction temperature 0-100C essary to use catalysts in the reactions, e.g. copper or copper chloride.
  • Processes l, 2, 3a and 3b may be carried out at normal pressure (3a at up to atmospheres absolute pressure) and in solvents or diluents.
  • Suitable solvents or diluents are e.g., ethers and ethereal compounds, such as diethyl ether, dipropyl ether, dioxan, dimethoxyethane, tetrahydrofu'ran; amides, such as N,N-
  • dialkylated carboxylic amides dialkylated carboxylic amides; aliphatic, aromatic and halogenated hydrocarbons, in particular benzene, toluene, xylenes, chloroform, chlorobenzene; nitriles, such as acetonitrile; dimethyl sulphoxide, ketones such as acetone, methyl ethyl ketone.
  • the compounds of the formula I display a broad biocidal activity and are therefore suitable for combating various plant and animal pests and as plant growth regulators.
  • the compounds of the formula possess insecticidal and acaricidalt properties which are superior to those of know, analogous compounds, and they may be used against all development stages, e.g., eggs, larvae, pupae, nymphs and addults, of insects and representatives of the order Acarina, for example against insects of the families:
  • the active substances of the formula I are also suitable for combating representatives of the division Thallophyta, e.g., viruses, bacteria and fungi. They thus possess fungicidal properties against phytophathogenic fungi on various cultivated plants, such as cereals, maize, rice, vegetables, ornamental plants, fruit trees, vines, farms products, etc.
  • the active sub stances of theformula I are active in particular against phytopahtogenic fungi belonging to the following classes: Oomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Denteromycetes.
  • the new active substance can also be used for treating seeds, fruits, tubers etc., and the protecting them from fungus infections, for example from smut fungi of all kinds, such as Ustilaginales, e.g. Ustilago, Tilletia, Urocystis, Turbicinia and Phoma types.
  • fungus infections for example from smut fungi of all kinds, such as Ustilaginales, e.g. Ustilago, Tilletia, Urocystis, Turbicinia and Phoma types.
  • the compounds of the formula I are suitable for combating plant pathogenic nematodes.
  • the compounds of the formula I may be used as pure active substance or together with suitable carriers and- /or additives.
  • suitable carriers and additives can be solid or liquid and correspond to the substances conventionally used in formulation technique such, for example, as solvents dispersants, wetting agents, adhesives, thickeners, binders and/or fertilisers.
  • the compounds of the formula I may be processed to dusts, emulsion concentrates, granules, dispersions, sprays, to solutions, or suspensions in the conventional formulation which is commonly employed in application technology. Mention may also be made of cattle clips and spray races," in which aqueous preparations are used.
  • the agents according'to the invention are manufactured in known manner by intimately mixing and/or grinding active substances of the formula I with the suitable carriers, optionally with the addition of dispersants or solvents which are inert towards the active substances.
  • the active substances may take and be used in the following forms:
  • Dusts, tracking agents, granules, coated granules, impregnated granules and homogeneous granules are particularly preferred.
  • the active substances are mixed with solid carriers.
  • suitable carriers are, for example, kaolin, talcum, bo- Ius, loess, chalk, limestone, ground limestone, attaclay, dolomite, diatomaceous earth, precipitated silica, alkaline earth silicates, sodium and potassium aluminium silicates (feldspar and mica), calcium and magnesium sulphates, magnesium oxide, ground synthetic materials, fertilisers, for example ammonium sulphate, ammonium phosphate, ammonium nitrate, urea, ground vegetable products, such as corn meal, bark dust, sawdust, nutshell meal, cellulose powder, residues of plant extractions, activated charcoal etc.
  • These substances can either be used alone or in admixture with one another.
  • Granules can be very easily manufactured by dissolving an active substance of the formula I in an organic solvent and applying the resulting solution to a granulated material, for example attapulgite, S10 granicalci um, bentonite etc. and then evaporatingthe solvent.
  • a granulated material for example attapulgite, S10 granicalci um, bentonite etc. and then evaporatingthe solvent.
  • Polymer granules can also be manufactured by mixing the active substances of the formula I with polymerisable compounds (urea/formaldehyde; dicyandiamide/formaldehyde; melamine/formaldehyde or others), whereupon a mild polymerisation is carried out that does not affect the active substances and in the process of which the granulation is carried out during the gel formation.
  • polymerisable compounds urea/formaldehyde; dicyandiamide/formaldehyde; melamine/formaldehyde or others
  • porous polymer granules urea/formaldehyde, polyacrylonitrile, polyester or others
  • the active substances for example in the form of their solutions (in a low boiling solvent) and to remove the solvent.
  • Polymer granules of this kind in the form of microgranules having a bulk density of 300 g/litre to 600 g/litre can also be manufactured with the aid of atomisers. The dusting can be carried out from aircraft over extensive areas of cultures of useful plants.
  • additives which stabilize the active substance and/or non-ionic, anionic and cationic surface active substances, which, for example, improve the adhesion of the active ingredients on plants or parts of plants (adhesives and agglutinants) and/or ensure a better wettability (wetting agents) and a dispersibility (dispersing agents).
  • Suitable adhesives are the following: olein/chalk mixture, cellulose derivates (methyl cellulose, carboxy methyl cellulose), hydroxyethyl glycol ethers of monoalkyl and dialkyl phenols having 5 to 15 ethylene oxide radicals per molecule and 8 to 9 carbon atoms in the alkyl radical, lignin sulphonic acids, their alkali metal and alkaline earth metal salts, polyethylene glycol ethers (carbowaxes), fatty alcohol polyethylene glycol ethers having 5 to 20 ethylene oxide radicals per molecule and 8 to 18 carbon atoms in the fatty alcohol moi ety, condensation products of ethylene oxide/propylene oxide, polyvinyl pyrrolidones, polyvinyl alcohols, condensation products of urea and formaldehyde, and also latex products.
  • olein/chalk mixture cellulose derivates (methyl cellulose, carboxy methyl cellulose), hydroxyethyl glycol ethers of monoalky
  • the water-dispersible concentrates of the active substance are agents which can be diluted with water to any concentration desired. They consist of active substance, carrier, optionally additives which stabilize the active substance, surface-active substanceand anti-foam agents and, optionally, solvents.
  • W'ettable powders and pastes are obtained by mixing and grinding the active substances with dispersing agents and pulverulentcarriers in suitable apparatusuntil homogeneity is attained.
  • Suitable carriers are, for example, those mentioned for the solid forms of application. In some cases it is advantageous to use mixtures of different carriers.
  • dispersing agents there can be used, for example, condensation products of sulfonated naphthalene and sulfonated naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde, as well as alkali, ammonium and alkaline earth metal salts of lignin sulfonic acid, in addition, a]-
  • kylaryl sulfonates alkali and alkaline-earth metal salts of dibutyl naphthalene sulfonic acid, fatty alcohol sulfates such as salts 'of sulfated hexadecanols, hep- 'tadecanols, octadecanols, and salts of sulfated fatty alcohol glycol ethers, the sodium salt of oleoyl ethionate, the sodium salt of oleoyl methyl tauride, ditertiary acetylene glycols, dialkyl fatty acid alkali and alkaline earth metal salts.
  • Suitable anti-foam agents are silicones.
  • the active substances are mixed, ground, sieved and strained with the additives cited hereinabove in such a. manner that, in wettable powders, the solid particle size of from 0.02 to 0.04 and in pastes, of 0.03 is notexdilauryl ammonium chloride and ceeded.
  • dispersing agents such as those cited above,-organic solvents and water are used.
  • suitable solvents are: alcohols, benzene, xylene, toluene dimethyl sulfoxide, and mineral oil fractions boiling between 120 and 350C.
  • the solvents must be practically odourless, not phytotoxic, inert to the active substances.
  • the agents according to the invention can be applied in the form of solutions.
  • the active substance or several active substances of the general formula I are dissolved in suitableorganic solvents, mixtures of solvents or in water.
  • suitableorganic solvents such as benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ethersulfate, benzyl ether, and benzyl ethersulfate, benzyl ether, and benzyl ethersulfate, benzylene glycol dimethoxysulfate, stearic acid, sulfate, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether ether sulfonyl sulfonyl sulfonyl
  • the content of active substance in the above described agents is between 0.1 to 95 percent, in which connection it should be mentioned that, in the case of application from aircraft or some other suitable means of application, it is possible to use concentrations of up to 99.5 percent or even pure active substance.
  • the active substances of the formula I can, for example, be formulated as follows: Dusts The following substances are used to manufacture (a) a 5 percent and (b) a 2 percent dust: v
  • the activesubstance ismixed with epichlorohydrin and dissolved with 6 parts ofacetone; the polyethylene glycol and cetyl polyglycol ether are then added. The thus obtained solution is sprayed on to kaolin, and the acetone subsequently evaporated in vacuo.
  • Wettable powder The following constituents are used for. the preparation of (a) a 40 percent, (b) and (d) a 10 percent wettable powder:
  • EXAMPLE 1 play ingest poison action against Spodoplera litoratis and Leptinotarsa decemlineala.
  • Systemic insecticidal action To determine the systemic action, rooted bean plants (Viciafabae) are put into a 0.01 percent aqueous active substance solution (obtained from a 10 percent emulsifiable concentrate). After 24 hours, aphids (Aphis fabae) are placed on the parts of the plant above the soil. The aphids are protected from contact and gas action by means ofa special device. The test is carried out at 24C and 70 percent relative humidity. In the above tests the compounds according to Example I displayed good insecticidal ingest poison action and systemic insecticidal action.
  • Example 1 act in the above test against adults and larvae of Rhicephalus bursa.
  • B. Boophilus microplus (larvae) Tests are carried out in each case with 20 OP- sensitive larvae using analogous dilution series as in the case of test A. (The resistance relates to the tolerability of Diazinon).
  • the compounds according to Example 1 act in these tests against sensitive and OR resistant larvae of Boophilus microplus.
  • Phaseolus vulgaris (dwarf beans) have an infested piece of leaf from a mass culture of Tetranychus urticae placed on them 12 hours before the test for the propyl, n-butyl, n-pentyl or C H OCH CH R reprelarvae, adults and eggs are evaluated after 7 days under a stereoscopic microscope and the result expressed in percentages. During the interim, the treated plants are kept in greenhouse compartments at 25C.
  • the compounds according to Example 1 are active in the above test against eggs, larvae and adults of Terranchus urticae.
  • the compounds according-to Example display good action against Meloidgyne Avenaria.
  • R represents ethyl
  • R represents propyl, n-butyl, C 'H OCH CH or n-amyl
  • R and R each represents methyl or ethyl
  • X and X represent hydrogen or chlo- .rine and Y represents oxygen.
  • a compound according to claim 2 of the formula 4.
  • a compound according to claim 2 of the formula C H O 5.
  • a compound according to claim 2 of the formula 19 I 20 8.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US00310507A 1971-12-03 1972-11-29 Phosphoric acid phenylsulphonamide esters Expired - Lifetime US3855362A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US05/508,592 US3934010A (en) 1971-12-03 1974-09-23 Insecticidal composition and method utilizing phosphoric acid phenylsulphonamide esters

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1761971A CH564908A5 (en) 1971-12-03 1971-12-03 (di)thiophosphoric acid esters - with biocidal activity
CH1386972A CH575211A5 (en) 1972-09-22 1972-09-22 (di)thiophosphoric acid esters - with biocidal activity

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US05/508,592 Division US3934010A (en) 1971-12-03 1974-09-23 Insecticidal composition and method utilizing phosphoric acid phenylsulphonamide esters

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US3855362A true US3855362A (en) 1974-12-17

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US00310507A Expired - Lifetime US3855362A (en) 1971-12-03 1972-11-29 Phosphoric acid phenylsulphonamide esters

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US (1) US3855362A (de)
JP (1) JPS4862940A (de)
BE (1) BE792185A (de)
CA (1) CA1050563A (de)
DD (1) DD108449A5 (de)
DE (1) DE2258751A1 (de)
EG (1) EG10757A (de)
ES (1) ES409218A1 (de)
FR (1) FR2162161B1 (de)
GB (1) GB1398584A (de)
HU (1) HU166825B (de)
IL (1) IL40681A (de)
IT (1) IT983177B (de)
NL (1) NL7215273A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4147781A (en) * 1977-11-25 1979-04-03 Rohm And Haas Company O,s-dialkyl o-benzamidophenyl phosphorothiolates and phosphorodithioates and pesticidal methods

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3309371A (en) * 1963-10-16 1967-03-14 American Cyanamid Co Organophosphorothioate compounds and method of preparing same

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1284753A (fr) * 1960-02-29 1962-02-16 American Cyanamid Co Thiophosphates organiques et procédé pour leur préparation

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3309371A (en) * 1963-10-16 1967-03-14 American Cyanamid Co Organophosphorothioate compounds and method of preparing same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Wagner et al., J. Med. Chem., 8(3), 1965, pages 377 to 383. *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4147781A (en) * 1977-11-25 1979-04-03 Rohm And Haas Company O,s-dialkyl o-benzamidophenyl phosphorothiolates and phosphorodithioates and pesticidal methods

Also Published As

Publication number Publication date
FR2162161A1 (de) 1973-07-13
BE792185A (fr) 1973-06-01
EG10757A (en) 1976-05-31
NL7215273A (de) 1973-06-05
FR2162161B1 (de) 1976-01-30
HU166825B (de) 1975-06-28
DE2258751A1 (de) 1973-06-07
ES409218A1 (es) 1975-12-16
JPS4862940A (de) 1973-09-01
GB1398584A (en) 1975-06-25
IT983177B (it) 1974-10-31
DD108449A5 (de) 1974-09-20
IL40681A (en) 1975-12-31
IL40681A0 (en) 1972-12-29
CA1050563A (en) 1979-03-13

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