US3513182A - Bicyclic-substituted sulfamides - Google Patents

Bicyclic-substituted sulfamides Download PDF

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Publication number
US3513182A
US3513182A US565673A US3513182DA US3513182A US 3513182 A US3513182 A US 3513182A US 565673 A US565673 A US 565673A US 3513182D A US3513182D A US 3513182DA US 3513182 A US3513182 A US 3513182A
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Prior art keywords
methyl
repellent
sulfamide
bicyclo
alkyl
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US565673A
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Hartmund Wollweber
Rudolf Hiltmann
Wolfgang Behrenz
Gerhard Muller
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Bayer AG
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Bayer AG
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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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C307/04—Diamides of sulfuric acids
    • C07C307/06—Diamides of sulfuric acids having nitrogen atoms of the sulfamide groups bound to acyclic carbon atoms

Definitions

  • the present invention relates to particular new bicyclic-substituted sulfamides, which surprisingly possess strong pest-repellent, especially insectand mite-repellent, properties, to their compositions with dispersible carrier vehicles, and to methods for the production and use thereof.
  • dimethyl phthalate (A) can be used as an insect repellent. This compound has already attained a substantial significance in practice although it possesses a repellent activity which only lasts for several hours.
  • R is selected from the group consisting of hydrogen and alkyl having 1 to 4 carbon atoms
  • R is selected from the group consisting of hydrogen, alkyl having 1 to 4 carbon atoms, and alkoxy having 1 to 3 carbon atoms
  • R' is alkyl having 1 to 4 carbon atoms, possess strong pest-repellent, and especially insectand mite-repellent, properties.
  • the particular new active compounds usable according to the present invention have a substantially higher repellent action against pests, such as insects and mites, than previously known insect-repellent compounds such as dimethyl phthalate (A).
  • the particular active compounds usable according to the present invention thus represent a valuable addition to the art.
  • the particular new active compounds according to the present invention can be prepared by numerous known processes.
  • the instant new compounds can be prepared by the process which comprises reacting bicyclically-substituted amines of the general formula:
  • bicyclically-substituted amines of general Formula Ila which can be used for the reaction and which are readily obtainable, for example, from diene addition products, and some also from natural substances, include the following: 2-bicyclo-[2,2,1J-heptylamine, Z-bicyclo-[2,2,l]-heptyl-methylamine, land 2-(2- bicyclo-[2,2,l]-heptyl-ethylamine, fenchylamine, bornylamine, isobornylamine, Z-amino-isocamphane, N-methylbornylamine, and (2-methyl-bicyclo-[2,2,1]-heptyl-2)- methylamine.
  • the amines of general Formula IId are known. The following may be mentioned, by way of example: methylamine, dimethylamine, methyl-ethylamine, diethylamine, isopropylamine, n-butylamine, isobutylamine, tert.-butylamine, di-n-butylamine, methyl-butylamine, di-n-propylamine, methyl-butylamine, di-isobutylamine, N,O-dimethyl-hydroxylamine and N,O-diethyl-hydroxylamine.
  • the sulfamic acid chlorides of general Formula IIc usable for the reaction with the amines of general Formula IId are derived from the above amines of general Formula 11a and can be prepared from the latter in known manner, for example, by reaction with sulfuryl chloride.
  • the sulfamic acid chlorides of general Formula IIb are known.
  • solvents such as aromatic hydrocarbons, ethers, ketones and esters
  • acid-binding agents such as triethylamine, pyridine, sodium carbonate or sodium hydroxide.
  • reaction t mperatures used are preferably between about 0 and C.
  • the reactions are expediently carried out with approxi mately equirnolar amounts of the reaction components, in the presence of at least the equivalent amount of an acidbinding agent and in the simultaneous presence of a solvent.
  • the acid-binding agents may also be replaced by an excess of the corresponding amine component.
  • Working up is carried out in conventional manner.
  • the particular new compounds according to the present inv ntion advantageously exhibit a strong repellent action against arthropods, and a low toxicity toward warmblooded animals. The effect lasts a long time.
  • the instant compounds can, therefore, be used, with good results, for repelling obnoxious sucking and biting insects and mites.
  • the sucking insects contemplated herein essentially include mosquitoes, such as the species Aedes, Culex and Anopheles; sand flies such as Phlebotomes; biting flies, such as Culicoides species; buffalo gnats, such as the Simulium types; stinging flies, such as the stable fly (Stomoxys calcitrans), the tsetse flies (Glossina species), horse flies, such as the Tabanus, Haemotopota and Chrysops species; the housefly (Musca domestica); the lesser housefly (Fannia canicularis); the meat flies, such as Sarcophaga carnaria; flies causing myiasis such as Lucilia cu'prina, Chrysomyia chloropyga, Hypoderma bovis, Hypoderma lineala, Dermato bia hominis, Oeslrus ovis, Gasterophilus intestinalis and coclzli
  • the biting insects contemplated herein essentially include cockroaches, such as the German cockroach (BIattelIa germanica), the oriental beetle (Blatta orientalis); beetles, such as the grain weevil (Sitophilus granarius), the stag beetle (Hylotrupes bajulus), the death watch beetle (Anobium punctatum), the leather beetl (Dermestes lardarium), the mealworm beetle (Tenebrio molitor) and termites, such as Reticulitermes lucifugus; and ants, such as Lasius niger; and the like.
  • cockroaches such as the German cockroach (BIattelIa germanica), the oriental beetle (Blatta orientalis); beetles, such as the grain weevil (Sitophilus granarius), the stag beetle (Hylotrupes bajulus), the
  • the mites contemplated herein include ticks, such as Ornithodoros moubata, Boophilus microplus and Amblyomma h braeum, and mites in the stricter sense, such as Dermanyssus gallinae and Sarcoptes scabiei; and the like.
  • the active compounds of the instant invention can be used as pest-repellents either alone or in admixture with solid or liquid carriers or diluents.
  • the active compounds according to the instant invention can be utilized, if desired, in the form of the usual formulations or compositions with dispersible carrier vehicles, such as solutions, emulsions, suspenion, emulifiable concentrates, spray powders, pastes, soluble powders, dusting agents, granulates, ointments, oils, lacquers, sprays, etc.
  • dispersible carrier vehicles such as solutions, emulsions, suspenion, emulifiable concentrates, spray powders, pastes, soluble powders, dusting agents, granulates, ointments, oils, lacquers, sprays, etc.
  • carrier vehicle assistants e.g., surface-active agents, including emulsifying agents and/or dispersing agents, whereby, for example, in the case where water is used as diluent, organic solvents may be added as auxiliary solvents (cf. Agricultural Chemicals, March 1960, pages 35-38).
  • dispersible liquid diluent carriers such as aromatic hydrocarbons (for instance, benzene, toluene, xylene, etc.), halogenated, especially chlorinated, aromatic hydrocarbons (for instance, chlorobenzenes), parafiins (for instance, petroleum fractions), chlorinated aliphatic hydrocarbons (for instance, methylene chloride, etc.), alcohols (for instance, methanol, ethanol, propanol, butanol, etc.), animal and vegetable fats (for instance, lanolin, olive oil, nut oils, etc.), amines (for instance, ethanolamine, etc.),
  • aromatic hydrocarbons for instance, benzene, toluene, xylene, etc.
  • halogenated especially chlorinated, aromatic hydrocarbons (for instance, chlorobenzenes), parafiins (for instance, petroleum fractions), chlorinated aliphatic hydrocarbons (for instance, methylene chloride, etc.), alcohols
  • amides for instance, dimethyl formamide, etc.
  • sulfoxides for instance, dimethyl sulfoxide, etc.
  • ketones for instance, acetone, etc.
  • water as well as dispersible finely divided solid carriers, such as ground natural minerals (for instance, kaolins, alumina, silica, chalk i.e., calcium carbonate, talc, kieselguhr, etc.) and ground synthetic minerals (for instance, highly dispersed silic acid, silicates, e.g., alkali silicates, etc.), whereas the following may be chiefly considered for use as carrier vehicle assistants, e.g., surface-active agents, for this purpose: emulsifying agents, such as non-ionic and anionic emulsifying agents (for instance, polyethylene oxide esters or fatty acids, polyethylene oxide ethers of fatty alcohols, alkyl sulfonates, aryl sulfonates, etc., and especially alkyl ary
  • the active compounds according to the instant invention may be present in such formulations or compositions in the form of mixtures with one another and with other known active substances, if desired.
  • substances according to the invention may be employed by themselves as the artisan will appreciate, in the form of their compositions with solid or liquid dispersible carrier vehicles or other known compatible active agents, or in the form of particular dosage preparations for specific application made therefrom, such as solutions, emulsions, suspensions, powders, pastes, ointm nts, oils, lacquers, sprays, and granulate which are thus ready for use.
  • carrier composition mixtures in which the active compound is present in an amount substantially between about 0.1-95% by weight, and preferably 0.5-% by weight of the mixture
  • carrier composition mixtures suitable for direct application or field application generally contemplate those in which the active compound is present in an amount substantially between about 0.01 and preferably 0.1 and 80%, by weight of the mixture.
  • compositions which comprise mixtures of a dispersible carrier vehicle, such as 1) a dispersible carrier solid, or (2) a dispersible carrier liquid preferably including a carrier vehicle assistant, e.g., surfaceactive agent, such as an emulsifying agent and/or a dispersing agent, and an amount of the active compound whic his effective for the purpose in question and which is generally between about 0.01 and 95% by weight of the mixture.
  • a dispersible carrier vehicle such as 1) a dispersible carrier solid, or (2) a dispersible carrier liquid preferably including a carrier vehicle assistant, e.g., surfaceactive agent, such as an emulsifying agent and/or a dispersing agent, and an amount of the active compound whic his effective for the purpose in question and which is generally between about 0.01 and 95% by weight of the mixture.
  • the present invention contemplates methods of repelling pests, especially insects and acarids, such as mites, which comprise applying to at least one of (a) such pests and (b) their habitat, a pest-repellent, especially insect-repellent and/or acarid-repellent, such as mite-repellent, effective amount of the particular active compound of the invention alone or together with a carrier vehicle, as noted above.
  • a pest-repellent especially insect-repellent and/or acarid-repellent, such as mite-repellent
  • effective amount of the particular active compound of the invention alone or together with a carrier vehicle, as noted above.
  • the instant formulations or compositions are applied in the usual manner, for example, by spraying, atomizing, vaporizing, scattering dusting, watering, sprinkling, pouring, rubbing, and the like.
  • the instant compounds may be used effectively not only in plant protection but also generally against insects and acarids, specifically for protection against insects and mites.
  • the active compounds are applied to human or animal skin, or clothes or other articles are impregnated with them.
  • the substances to be protected are either treated directly with the instant active agents or the latter are applied to an area around the substances to be protected, thus creating inhibition zones against the penetration of the pests.
  • EXAMPLE 1 Repellent test/mosquitoes Test insect: Aedes aegypti Solvent: alcohol To produce a suitable preparation of the particular active compound, 5 parts by weight of such active compound are mixed with 100 parts by volume of the stated solvent.
  • a patch of hair is shaven off from the backs of guinea pigs to the extent of 50 cm. 0.4 cc. of the resulting preparation of the given active compound are uniformly distributed over this shaven area.
  • the animals are then placed in narrow cages of fine wire mesh which leaves free the shaven area of the back of the respective animal.
  • the cages containing the guinea pigs are placed for minutes in larger cages containing several thousand hungry mosquitoes flying about.
  • the mesh of the narrow cages containing the guinea pigs is such that the mosquitoes may pass therethrough,.the mesh of the larger cages is fine enough to keep the mosquitoes therewithin.
  • the guinea pigs are observed to see whether the mosquitoes bite them on the treated area.
  • the placing of the guinea pig cages into the larger cages is repeated once every hour for a 10 minute period.
  • the repellent action is regarded as terminated when the guinea pig is bitten by more than one mosquito during the given 10 minute period of observation.
  • N- (Z-methyl-bicyclo- [2,2, l -hept-2-yl -methyl] N-methyl-amine (B.P. 84 C./l5 mm. Hg.) used as starting material is obtained by monomethylation of N- (2-methyl-bicyclo-[2,2,1]-hept2-yl)-methyl-amine which, in turn, is formed by hydrogenation of the Diels-Adler addition product of methacrylonitrile with cyclopentadiene.
  • n a number from 0 to 2
  • R is selected from the group consisting of hydrogen and alkyl having 1 to 4 carbon atoms
  • R" is selected from the group consisting of hydrogen, alkyl having 1 to 4 carbon atoms, and alkoxy having 1 to 3 carbon atoms
  • R is alkyl having 1 to 4 carbon atoms
  • p is a number from 1 to 2 with the proviso that where p is 1 then the remaining 9 symbols X and the 2 symbols Y each, respectively, represents a number selected from the group consisting of hydrogen and methyl, with at least 8 and at most 11 of said remaining 9 symbols X and 2 symbols Y being hydrogen, and that where p is 2, then the remaining 9 symbols X and the 4 symbols Y each, respectively, represents a member selected from the group consisting of hydrogen and methyl, with at least 11 and at most 13 of said remaining 9 symbols X and the 4 symbols Y being hydrogen; and
  • R represents hydrogen, or alkyl having 1-4 carbon atoms, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec.-butyl, tert.-butyl, especially methyl;
  • R" represents hydrogen; or alkyl having 1-4 carbon atoms, such as methyl to tert.-butyl inclusive as noted above; or alkoxy having 1-3 carbon atoms, such as methoxy, ethoxy, n-pro'poxy and iso-propoxy;
  • n is a number from 0 to 3 inclusive
  • n is a number from 0 to 2 inclusive
  • p is a number from 1 to 2.
  • the same preferably contemplatess monomethyl or trimethyl, or of course, otherwise hydrogen; and that with respect to the designation C H the same may represent a bond between the ring carbon atom and the adjacent N atom of the adjacent N atom of the sulfamide group where n is 0, or the methylene group where n is 1, or 1,2-ethylene (i.e., dimethylene-CH CH or 1,1-ethylene (i.e., methyl-methylene where n is 2.
  • arthropod and arthropod-repellent may be defined as encompassing specifically both insects and acarids within the contemplation of their meaning, for convenience in determining the collective aspects of utility herein.
  • the insects and acarids may be considered herein collectviely as arthropods to be combated collectively in accordance with the invention, and hence the insect-repellent and/ or acarid-repellent activity may be termed arthroped-repellent activity, and the concomitant combative or eifective amount used in accordance with the invention will be an arthropod-repellent effective amount which in essence means an insect-repellent or acarid-repellent effective amount of the active compound for the desired purpose.
  • n is a number from 0 to 2
  • R is selected from the group consisting of hydrogen and alkyl having 1 to 4 carbon atoms
  • R is selected from the group consisting of hydrogen, alkyl having 1 to 4 carbon atoms, and alkoxy having 1 to 3 carbon atoms
  • R' is alkyl having 1 to 4 carbon atoms
  • p is a number from 1 to 2 with the proviso that where p is 1 then the remaining 9 symbols X and the 2 symbols Y each, respectively, represents a member selected from the group consisting of hydrogen and methyl, with at least 8 and at most 11 of said remaining 9 symbols X and 2 symbols Y being hydrogen, and that where p is 2, then the remaining 9 symbols X and the 4 symbols Y each, respectively, represents a member selected from the group consisting of hydrogen and methyl, with at least 11 and at most 13 of said remaining 9 symbols X and the 4 symbols Y being hydrogen.
  • R' is selected from the group consisting of hydrogen and alkyl having 1 to 4 carbon atoms
  • R is selected from the group consisting of hydrogen, alkyl having 1 to 4 carbon atoms, and alkoxy having 1 to 3 carbon atoms
  • R' is alkyl having 1 to 4 carbon atoms.
  • Fatben 1249 y (22:5 UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3 a 513 182 D t d May 19 1970 fl Hartmund Wollweber Rudolf Hiltmann, Wolfgang Behrenz,

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US565673A 1965-07-24 1966-07-18 Bicyclic-substituted sulfamides Expired - Lifetime US3513182A (en)

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BE (1) BE684461A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CH (1) CH480010A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DE (1) DE1542785A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
ES (1) ES329428A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
GB (1) GB1111706A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
IL (1) IL26080A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
NL (1) NL6610372A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
SE (1) SE335252B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MY147767A (en) 2004-06-16 2013-01-31 Janssen Pharmaceutica Nv Novel sulfamate and sulfamide derivatives useful for the treatment of epilepsy and related disorders
US8283478B2 (en) * 2005-05-20 2012-10-09 Janssen Pharmaceutica Nv Process for preparation of sulfamide derivatives
US8492431B2 (en) 2005-12-19 2013-07-23 Janssen Pharmaceutica, N.V. Use of benzo-fused heterocycle sulfamide derivatives for the treatment of obesity
US8497298B2 (en) 2005-12-19 2013-07-30 Janssen Pharmaceutica Nv Use of benzo-fused heterocycle sulfamide derivatives for lowering lipids and lowering blood glucose levels
US8716231B2 (en) 2005-12-19 2014-05-06 Janssen Pharmaceutica Nv Use of benzo-fused heterocycle sulfamide derivatives for the treatment of pain
US8691867B2 (en) 2005-12-19 2014-04-08 Janssen Pharmaceutica Nv Use of benzo-fused heterocycle sulfamide derivatives for the treatment of substance abuse and addiction
US8937096B2 (en) 2005-12-19 2015-01-20 Janssen Pharmaceutica Nv Use of benzo-fused heterocyle sulfamide derivatives for the treatment of mania and bipolar disorder
AU2007253814A1 (en) 2006-05-19 2007-11-29 Janssen Pharmaceutica N.V. Co-therapy for the treatment of epilepsy
EA018567B1 (ru) 2008-06-23 2013-08-30 Янссен Фармацевтика Нв Кристаллическая форма (2s)-(-)-n-(6-хлор-2,3-дигидробензо[1,4]диоксин-2-илметил)сульфамида
US8815939B2 (en) 2008-07-22 2014-08-26 Janssen Pharmaceutica Nv Substituted sulfamide derivatives

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2768971A (en) * 1954-05-26 1956-10-30 Ici Ltd Preparation of alkyl-aryl-ureas
US2829038A (en) * 1954-05-14 1958-04-01 Union Chimique Belge Sa Method of controlling plant growth
US3288851A (en) * 1961-05-06 1966-11-29 Ciba Ltd Process for the bromination of phenylureas
US3304167A (en) * 1960-12-15 1967-02-14 Hercules Inc Norbornyl and substituted norbornyl ureas and thioureas, weed control compositions and methods

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2829038A (en) * 1954-05-14 1958-04-01 Union Chimique Belge Sa Method of controlling plant growth
US2768971A (en) * 1954-05-26 1956-10-30 Ici Ltd Preparation of alkyl-aryl-ureas
US3304167A (en) * 1960-12-15 1967-02-14 Hercules Inc Norbornyl and substituted norbornyl ureas and thioureas, weed control compositions and methods
US3288851A (en) * 1961-05-06 1966-11-29 Ciba Ltd Process for the bromination of phenylureas

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CH480010A (de) 1969-10-31
ES329428A1 (es) 1967-05-16
GB1111706A (en) 1968-05-01
IL26080A (en) 1970-01-29
DE1542785A1 (de) 1970-05-06
NL6610372A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1967-01-25
BE684461A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1967-01-23
SE335252B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1971-05-17

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