US3929883A - Phenylformamidine derivatives - Google Patents

Phenylformamidine derivatives Download PDF

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Publication number
US3929883A
US3929883A US344461A US34446173A US3929883A US 3929883 A US3929883 A US 3929883A US 344461 A US344461 A US 344461A US 34446173 A US34446173 A US 34446173A US 3929883 A US3929883 A US 3929883A
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United States
Prior art keywords
carbon atoms
compounds
parts
alkyl
active substances
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US344461A
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English (en)
Inventor
Dieter Durr
Georg Pissiotas
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis Corp
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Ciba Geigy Corp
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Filing date
Publication date
Priority claimed from CH473072A external-priority patent/CH564304A5/xx
Priority claimed from CH473172A external-priority patent/CH564305A5/de
Application filed by Ciba Geigy Corp filed Critical Ciba Geigy Corp
Application granted granted Critical
Publication of US3929883A publication Critical patent/US3929883A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds

Definitions

  • ABSTRACT Compounds of the formula wherein R represents alkyl having 1 to 4 carbon atoms, alkenyl having 3 to 5 carbon atoms, or alkynyl having 3 to 6 carbon atoms,
  • R represents hydrogen, alkyl having 1 to 4 carbon atoms, alkenyl having 3 to 5 carbon atoms, or alkynyl having 3 to 6 carbon atoms,
  • R represents alkyl having 1 to 4 carbon atoms
  • R represents alkyl having 1 to 4 carbon atoms
  • R represents hydrogen, or alkyl having 1 to 4 carbon atoms
  • X represents an inorganic or organic acid radical and their acid addition salts, process for the manufacture of these compounds, compositions containing these compounds as active ingredients and use of these compounds for the control of parasitic pests on domestic and productive animals.
  • R represents hydrogen, alkyl having 1 to 4 carbon atoms, alkenyl having 3 to 5 carbon atoms, or alkynyl having 3 to 6 carbon atoms,
  • R represents alkyl having 1 to 4 carbon atoms
  • R represents alkyl having 1 to 4 carbon atoms
  • R represents hydrogen, or alkyl having 1 to 4 carbon atoms
  • X represents an inorganic or organic acid radical.
  • alkyl, alkenyl, alkynyl or alkoxy groups applicable for formula I can be straight-chain or branched, interrupted with hetero atoms, unsubstituted, or substituted, e.g. with halogen.
  • Halogen is fluorine, chlorine, bromine and/or iodine.
  • Examples of such groups are inter alia: methyl, methoxy, trifluoromethyl, ethyl, ethoxy, 2-chloroethyl, propyl, propoxy, isopropyl, isopropoxy, n-butyl, nbutoxy, i, sec.- or tert.-butyl, allyl, methallyl, lchloroallyl, 2-chloroallyl, l-butenyl, 2-butenyl, 3-butenyl, propargyl or isobutynyl.
  • R represents hydrogen, methyl, ethyl, propyl, isopropyl or n-butyl
  • R represents methyl, ethyl or isopropyl
  • R represents methyl, ethyl, propyl, isopropyl, sec.-
  • X represents an inorganic or organic acid radical.
  • the compounds of formula I and la can be produced I by methods known per se; for example, by the following method:
  • the compounds of formula I have a broad biocidal action, and can be used for the control of parastic pests on domestic and productive animals.
  • the compounds of formula I possess, in particular, acaricidal properties.
  • the compounds according to the invention are appreciably more stable than analogous compounds disclosed in the literature, and have therefore a clearly more persistent action against all development stages, such as eggs, larvae and adults of members of the order acarina, particularly of mites, red spider mites and ticks, such as, e.g. of the families lxodidae, Argasidae, Tetranychidae and Dermanyssidae.
  • Suitable additives include the following active substances:
  • HEPTACHLOR methylene indane
  • ADRlN 1 ,2,3,4, 1 0,1 O-hexachloro-6,7-epoxy-1 ,4,4oz,5 ,6,7,8 ,8aoctahydro-exo-1,4-endo-5 ,8-dimethanonaphthalene
  • DIELDRIN 1,2,3 ,4, l 0, l O-hexachloro-S ,7-epoxy-1,4,4oz,5,6,7,8,8a-
  • Suitable carriers and additives may be solid or liquid, and correspond to the substances common in formulation practice, such as, eg natural and regenerated substances, solvents, dispersing agents, wetting agents, adhesives, thickeners, binders and/or fertilisers.
  • the compounds of formulae 1 and la can be processed into the form of dusts, emulsion concentrates, granulates, dispersions, sprays, or solutions, the formulation of these preparations being effected in a manner commonly known in practice. Also to be mentioned are cattle dips and spray races, in which aqueous preparations are used.
  • the agents according to the invention are produced in a manner known per se by the intimate mixing and- /or grinding of active substances of formulae l and la with the suitable carriers, optionally with the addition of dispersing agents or solvents which are inert to the active substances.
  • the active substances can be obtained and used in the following preparation forms:
  • solid preparations dusts, scattering agents, granulates
  • coated granulates impregnated granulates and homogeneous granulates
  • the solid preparations are produced by the mixing of the active substances with solid carriers.
  • Suitable carriers are, e.g. kaolin, talcum, bole, locss, chalk, limestone, ground limestone, attapulgite, dolomite, diatomaceous earth, precipitated silicic acid, alkaline-earth silicates, sodium and potassium aluminium silicates (feldspar and mica), calcium and magnesium sulphates, magnesium oxide, ground synthetic materials, fertilisers such as ammonium sulphate, ammonium phosphate, ammonium nitrate, urea, ground vegetable products such as bran, bark dust, sawdust, ground nutshells, cellulose powder, residues of plant extractions, active charcoal, etc., alone or in admixture with each other. 1
  • Granulates can be very easily prepared by a process in which an active substance of formula I or la is dissolved in an organic solvent, the thus obtained solution applied to a granulated mineral, e.g. attapulgite, SiO granicalcium, bentonite, etc., and the organic solvent then evaporated off.
  • a granulated mineral e.g. attapulgite, SiO granicalcium, bentonite, etc.
  • polymer granulates in this case the active substances of formula I or la are mixed with polymerisable compounds (urea/formaldehyde; dicyandiamide/formaldehyde; melamine/formaldehyde, or others); polymerisation is then carefully carried out in a manner which leaves the active substances unaffected, and granulation performed actually during the gel forming process.
  • polymerisable compounds urea/formaldehyde; dicyandiamide/formaldehyde; melamine/formaldehyde, or others.
  • Polymer granulates of this kind can be also sprayed in the form of microgranulates, having bulk weights of preferably 300 g/liter to 600 g/liter, with the aid of spray apparatus. Spraying can be carried out over extensive areas of useful plant crops by the use of aeroplanes.
  • Granulates can also be obtained by the compacting of the carrier material with the active substances and additives, and a subsequent reducing operation.
  • additives stabilising the active substance and/or nonionic, anion-active and cation-active substances which improve, e.g. the adhesiveness of the active substances on plants and parts of plants (adhesives and agglutinants), and/or ensure a better wettability (wetting agents) as well as dispersibility (dispersing agents).
  • the following substances are, for example, suitable: olein/lime mixture, cellulose derivatives (methyl cellulose, carboxymethyl cellulose), hydroxyethylene 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, ligninsulphonic acid, the alkali metal and alkaline-earth metal salts thereof, polyethylene glycol ethers (carbowaxes), fatty alcohol polyglycol ethers having 5 to 20 ethylene oxide radicals per molecule and 8 to 18 carbon atoms in the fatty alcohol moiety, condensation products of ethylene oxide, propylene oxide, polyvinylpyrrolidones, polyvinyl alcohols, condensation products of urea and formaldehyde, as well as latex products.
  • olein/lime mixture cellulose derivatives (methyl cellulose, carboxymethyl cellulose), hydroxyethylene glycol ethers of monoalkyl and dialkyl phenols having 5
  • Water-dispersible concentrates of active substances are agents which can be diluted with water to obtain any desired concentration. They consist of active substance, carrier, optionally additives which stabilise the active substance, surface-active substances, and anti-foam agents and, optionally, solvents.
  • the wettable powders and pastes are obtained by the mixing and grinding of the active substances with dispersing agents and pulverulent carriers, in suitable devices, until homogeneity is obtained.
  • Suitable carriers are, c.g. those previously mentioned in the case of 3,929,883 1 1 1 2 solid preparations. It is advantageous in some cases to
  • the active substance is mixed with epichlorohydrin use mixtures of different carriers.
  • the sulphonated naphthalene and sulphonated naphthalene thus obtained solution is sprayed on to kaolin, and the derivatives with formaldehyde, condensation products 5 t n subsequently evaporated in vacuoof naphthalene or of naphthalenesulphonic acids with w l powder;
  • Phenol l formaldehyde as as alkali, ammonium
  • the following constituents are used for the preparaand alkaline-earth metal salts of ligninsulphonic acid, tion f (a) a (b) and (C) a 2 and (d) a 0% also alkylarylsulphonates, alkali metal salts and alkawettable powderZ line-earth metal salts of dibutyl naphthalenesulphonic l0 acid, fatty alcohol sulphates such as salts of sulphated a 40 art: )f active substance.
  • dialkyl dilauryl ammonium chloride dialkyl dilauryl ammonium chloride, and fatty acid alkali-metal and alkaline-earth metal salts.
  • Suitable anti-foam agents are, e.g. silicones.
  • able solvents are, e.g. alcohols, benzene, xylene, tolu- 3 P L a -71 Sal's saturate at y a c0 0 su p ates.
  • dlmethylsulphoxldei and mmeral fractlons boll 5 parts of naphthalencsulphonic acid/formaldehyde ing 11'! the range of 120 to 350C.
  • the solvents must be condensate. practically odourless, non-phytotoxic, and inert to the 82 pans of active substances.
  • the agents according to the invention can be used in the form of solutions.
  • the active substance, or several active substances, of the general formula 1 and/or la is dissolved in suitable organic solvents, solvent mixtures, or water.
  • organic solvents it is possible to use aliphatic and aromatic hydrocarbons, their chlorinated derivatives, alkylnaphthalenes, mineral oils on their own or in admixture with each other.
  • the content of active substance in the above de- 40 scribed agents is between 0.1 and 95%; it is to be men-
  • the active substances are intimately mixed, in suitable mixers, with the additives, the mixture being then ground in the appropriate mills and rollers.
  • wettable powders are obtained which can be diluted with water to give suspensions of any desired concentration.
  • Emulsifiable concentrates are:
  • the active substances of formulae I and la are pre 25 parts of epoxidised Vegetable 0" p -gas follows: l0 parts of an alkylarylsulphonate/fatty alcoholpolyglycol ether mixture 5 parts of dimethylformamide, Dusts' 57.5 parts of xylene.
  • the active substances are mixed and ground with the carriers. 5 parts of active substance,
  • EXAMPLE 1 5 parts of active substance, 81%; zgfi'gg y 'g ether Production of N,N-dimethyl-N-(2,6-diethylphenyl)- 3.50 parts of polyethylene glycol, formamidine. Parts knoll (Pamclc Production of the compound of the formula 01-1 N cu N 40 ml of dimethylformamide and 40 ml of thionyl chloride are stirred for 2 hours in 200 ml of absolute toluene at 40C; an addition is then made dropwise at 40-50C of 59.8 g of 2,6-diethylaniline diluted with 200 ml of anhydrous toluene.
  • reaction mixture is heated slowly for 4 hours to the boiling point, and refluxed for a further 5 hours.
  • the reaction mixture is cooled; ice water is added, the whole rendered alkaline with sodium hydroxide solution, and the organic phase separated and dried over sodium sulphate. Distillation yields the product in ca. 85% yield; B.P.: 7779C/0.03 Torr.
  • test tubes 186 187C into a small glass test tube, and the test tubes them immersed for 1 to 2 minutes in 2 ml of an aqueous emulsion from a dilution series of 100, 10, 1 and 0.1 ppm of test substance.
  • the tubes were then sealed with a standardised cotton plug, and inverted so that the active substance emulsion could be absorbed by the cotton wool.
  • the compounds according to Example 1 were effective, in the above test, against adults and larvae of Rhipicephalus bursa.
  • the compounds according to Example 1 were effective in the above test against sensitive larvae of Boophilus microplus.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US344461A 1972-03-29 1973-03-23 Phenylformamidine derivatives Expired - Lifetime US3929883A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH473072A CH564304A5 (en) 1972-03-29 1972-03-29 Substd phenylformamidines
CH473172A CH564305A5 (en) 1972-03-29 1972-03-29 Substd phenylformamidines - acaricides

Publications (1)

Publication Number Publication Date
US3929883A true US3929883A (en) 1975-12-30

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ID=25696154

Family Applications (1)

Application Number Title Priority Date Filing Date
US344461A Expired - Lifetime US3929883A (en) 1972-03-29 1973-03-23 Phenylformamidine derivatives

Country Status (19)

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US (1) US3929883A (enrdf_load_stackoverflow)
JP (1) JPS496124A (enrdf_load_stackoverflow)
AR (1) AR217029A1 (enrdf_load_stackoverflow)
AT (1) AT320611B (enrdf_load_stackoverflow)
BE (1) BE797442A (enrdf_load_stackoverflow)
BR (1) BR7302283D0 (enrdf_load_stackoverflow)
CA (1) CA1051027A (enrdf_load_stackoverflow)
CS (1) CS189605B2 (enrdf_load_stackoverflow)
DD (1) DD107907A5 (enrdf_load_stackoverflow)
DE (1) DE2315041A1 (enrdf_load_stackoverflow)
FR (1) FR2178117A1 (enrdf_load_stackoverflow)
GB (1) GB1422216A (enrdf_load_stackoverflow)
IL (1) IL41823A (enrdf_load_stackoverflow)
IT (1) IT988616B (enrdf_load_stackoverflow)
KE (1) KE2917A (enrdf_load_stackoverflow)
NL (1) NL7304037A (enrdf_load_stackoverflow)
SU (1) SU651643A3 (enrdf_load_stackoverflow)
YU (1) YU36156B (enrdf_load_stackoverflow)
ZA (1) ZA732129B (enrdf_load_stackoverflow)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111925303A (zh) * 2020-08-12 2020-11-13 广东嘉博制药有限公司 一种盐酸罗哌卡因杂质的制备方法

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4071556A (en) * 1974-03-11 1978-01-31 Stauffer Chemical Company Formamidine insecticidal compounds
FI760163A7 (enrdf_load_stackoverflow) * 1975-02-05 1976-08-06 Huyck Corp
JPS5516913A (en) * 1978-07-18 1980-02-06 Imaizumi Shigiyou Kk Paper making blanket in paper making machine and production
EP0015440A1 (de) * 1979-02-23 1980-09-17 Hoechst Aktiengesellschaft Substituierte N1-Vinyl-N1-methyl-N2-aryl-formamidine, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Schädlingsbekämpfungsmittel
GB9902592D0 (en) * 1999-02-06 1999-03-24 Hoechst Schering Agrevo Gmbh Fungicides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3119831A (en) * 1959-07-10 1964-01-28 Ici Ltd N-2-pyridyl-n'-(n-octyl or n-dodecyl)-formamidine
US3284289A (en) * 1962-03-08 1966-11-08 Duerr Dieter Method for protecting plants from fungi
US3557128A (en) * 1967-03-04 1971-01-19 Egyt Gyogyszervegyeszeti Gyar Certain pyridyl formamidine derivatives

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3119831A (en) * 1959-07-10 1964-01-28 Ici Ltd N-2-pyridyl-n'-(n-octyl or n-dodecyl)-formamidine
US3284289A (en) * 1962-03-08 1966-11-08 Duerr Dieter Method for protecting plants from fungi
US3557128A (en) * 1967-03-04 1971-01-19 Egyt Gyogyszervegyeszeti Gyar Certain pyridyl formamidine derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111925303A (zh) * 2020-08-12 2020-11-13 广东嘉博制药有限公司 一种盐酸罗哌卡因杂质的制备方法

Also Published As

Publication number Publication date
JPS496124A (enrdf_load_stackoverflow) 1974-01-19
FR2178117A1 (enrdf_load_stackoverflow) 1973-11-09
YU36156B (en) 1982-02-25
AT320611B (de) 1975-02-25
BE797442A (fr) 1973-09-28
GB1422216A (en) 1976-01-21
AR217029A1 (es) 1980-02-29
NL7304037A (enrdf_load_stackoverflow) 1973-10-02
SU651643A3 (ru) 1979-03-05
CA1051027A (en) 1979-03-20
DD107907A5 (enrdf_load_stackoverflow) 1974-08-20
IT988616B (it) 1975-04-30
KE2917A (en) 1979-03-09
CS189605B2 (en) 1979-04-30
IL41823A0 (en) 1973-05-31
YU82473A (en) 1981-06-30
BR7302283D0 (pt) 1974-06-27
AU5368873A (en) 1974-09-26
IL41823A (en) 1977-12-30
DE2315041A1 (de) 1973-10-11
ZA732129B (en) 1974-01-30

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