GB912895A - New substituted carbamates - Google Patents

New substituted carbamates

Info

Publication number
GB912895A
GB912895A GB4185160A GB4185160A GB912895A GB 912895 A GB912895 A GB 912895A GB 4185160 A GB4185160 A GB 4185160A GB 4185160 A GB4185160 A GB 4185160A GB 912895 A GB912895 A GB 912895A
Authority
GB
United Kingdom
Prior art keywords
methyl
carbamate
phenyl
dimethyl
compounds
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
Application number
GB4185160A
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.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of GB912895A publication Critical patent/GB912895A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • 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
    • C07C333/02—Monothiocarbamic acids; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof

Landscapes

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

Abstract

The invention comprises aryl carbamates of the formula <FORM:0912895/IV (b)/1> in which R and R1 are hydrogen atoms or alkyl radicals of 1-4 carbon atoms, R2 is alkyl, alkenyl, or alkynyl of 1-4 carbon atoms optionally containing a halogen atom, Y is CH2 or a direct bond, X is S, SO or SO2, Z is oxygen or sulphur, and 'aryl' is a benzene, diphenyl, or naphthalene nucleus optionally substituted by straight or branched chain alkyl radicals. These compounds may be obtained by reacting appropriate phenols with phosgene or thiophosgene so as to form chloroformic esters or chlorothioformic esters and these are reacted with ammonia or appropriate primary or secondary amines. They may also be obtained in some cases by reacting appropriate phenols with appropriate dialkyl-carbamic or thiocarbamic acid chlorides. If monoalkylamides are to be produced, appropriate phenols may be reacted with appropriate isocyanates or thioisocyanates. Phenols which may be used as starting materials include p-methylmercapto-phenol, p-methyl sulphinyl phenol, 3-methyl-4-methylsulphonyl phenol, and 2-hydroxy-5-methylsulphonyl diphenyl. The preparation of many compounds of the stated general formula is described including that of p-methylmercapto-phenyl carbamate and the corresponding N-methyl and N.N1-dimethyl compounds; p - methylsulphinyl-phenyl-N.N1-dimethyl-carbamate; p - methyl-mercapto-phenyl thiocarbamate and the corresponding N-methyl and N.N1-dimethyl compounds; 4 - methylsulphonyl-3-methyl-phenylN.N1-dimethyl-carbamate, 1-methylmercapto-2-naphthylN.N1-dimethyl-carbamate, p - ethyl mercapto-methyl-phenyl-N.N1-dimethyl carbamate; o-allylmercapto-phenyl-N-methyl-carbamate and the corresponding o-propargyl mercapto and o-(2-chloro-allylmercapto) compounds. The compounds are used in insecticidal and acaricidal preparations (see Group VI).ALSO:Pesticidal compositions comprise as active ingredient a carbamate of the general formula <FORM:0912895/VI/1> in which R and R1 represent hydrogen atoms or alkyl radicals of 1-4 carbon atoms, R2 is an alkyl, alkenyl, or alkynyl radical of 1-4 carbon atoms optionally containing a halogen atom, Y is -CH2- or a direct linkage, X is S, SO, or SO2, Z is O or S, and "aryl" is a benzene, diphenyl, or naphthalene nucleus which may be substituted by straight or branched alkyl radicals. Solid or liquid carriers may be present e.g. talc, chalk, bentonite, clay, water, alcohols, ketones, or liquid hydrocarbons. Emulsifiers, fertilizers, and other insecticides may be included. The compositions are effective against flies, mosquito larvae, mites, aphids, and caterpillars and may be used in concentrations of 0.00001 to 1.0%. They have a low toxic action on warm-blooded animals. Many compounds of the stated formula are mentioned including 4-methylmercapto-3-methyl - phenyl - N - methyl - carbamate, p-methylsulphonyl - phenyl - N.N - dimethyl thiocarbamate, 1 - methyl - mercapto - 2 - naphthyl-N.N - dimethyl - carbamate, and o - (2 - chloroallyl - mercapto) - phenyl - N - methyl - carbamate.
GB4185160A 1959-12-05 1960-12-05 New substituted carbamates Expired GB912895A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF30015A DE1162352B (en) 1959-12-05 1959-12-05 Process for the production of carbamic acid esters

Publications (1)

Publication Number Publication Date
GB912895A true GB912895A (en) 1962-12-12

Family

ID=7093564

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4185160A Expired GB912895A (en) 1959-12-05 1960-12-05 New substituted carbamates

Country Status (6)

Country Link
BE (1) BE597806A (en)
BR (1) BR6024675D0 (en)
CH (1) CH389314A (en)
DE (1) DE1162352B (en)
GB (1) GB912895A (en)
NL (2) NL131470C (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3313684A (en) * 1959-12-05 1967-04-11 Bayer Ag 3, 5-dimethyl-4-methylmercaptophenyl n-methyl carbamate and methods for combating insects
US3331894A (en) * 1963-03-04 1967-07-18 Hooker Chemical Corp o-(diloweralkoxythiophosphinylthioalkyl)phenyl n-loweralkyl carbamates
US3349115A (en) * 1963-02-19 1967-10-24 Hooker Chemical Corp Sulfur-containing carbamate insecticides
US3349116A (en) * 1963-02-20 1967-10-24 Hooker Chemical Corp Ortho hydrocarbyloxy alkenylenephenyl nu-lower alkylcarbamates
US3419663A (en) * 1963-03-04 1968-12-31 Hooker Chemical Corp Method for the control of insects using thioalkylphenyl carbamates
US3437684A (en) * 1964-07-04 1969-04-08 Bayer Ag 3,5-dimethyl-4-alpha-allyl mercaptophenyl-n-methyl carbamic acid ester
US3470236A (en) * 1964-06-27 1969-09-30 Bayer Ag Phenyl-n-methyl carbamic acid esters
FR2208890A1 (en) * 1972-12-01 1974-06-28 Bayer Ag
WO2002053529A1 (en) * 2000-12-29 2002-07-11 3M Innovative Properties Company High-boiling electrolyte solvent
US8846567B2 (en) 2009-03-25 2014-09-30 Bayer Cropscience Ag Active compound combinations having insecticidal and acaricidal properties

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19953775A1 (en) 1999-11-09 2001-05-10 Bayer Ag Active ingredient combinations with insecticidal and acaricidal properties
DE10015310A1 (en) 2000-03-28 2001-10-04 Bayer Ag Active ingredient combinations with insecticidal and acaricidal properties
DE102007045955A1 (en) 2007-09-26 2009-04-09 Bayer Cropscience Ag Active agent combination, useful e.g. for combating animal pests and treating seeds of transgenic plants, comprises substituted amino-furan-2-one compound and at least one compound e.g. diazinon, isoxathion, carbofuran or aldicarb
EP2127522A1 (en) 2008-05-29 2009-12-02 Bayer CropScience AG Active-agent combinations with insecticidal and acaricidal properties
EP2227951A1 (en) 2009-01-23 2010-09-15 Bayer CropScience AG Application of enaminocarbonyl compounds for combating viruses transmitted by insects
CN102421290B (en) 2009-03-25 2014-12-31 拜尔农作物科学股份公司 Nematicidal, insecticidal, and acaricidal combination of active substances, comprising pyridylethyl benzamide and insecticide

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL178971B (en) * 1953-06-09 Merck & Co Inc PROCESS FOR PREPARING ANTIBIOTICALLY ACTIVE PHARMACEUTICAL PREPARATIONS, AND PROCESS FOR PREPARING CEPHALOSPORIN DERIVATIVES SUITABLE FOR USE THEREIN.

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3313684A (en) * 1959-12-05 1967-04-11 Bayer Ag 3, 5-dimethyl-4-methylmercaptophenyl n-methyl carbamate and methods for combating insects
US3349115A (en) * 1963-02-19 1967-10-24 Hooker Chemical Corp Sulfur-containing carbamate insecticides
US3349116A (en) * 1963-02-20 1967-10-24 Hooker Chemical Corp Ortho hydrocarbyloxy alkenylenephenyl nu-lower alkylcarbamates
US3331894A (en) * 1963-03-04 1967-07-18 Hooker Chemical Corp o-(diloweralkoxythiophosphinylthioalkyl)phenyl n-loweralkyl carbamates
US3419663A (en) * 1963-03-04 1968-12-31 Hooker Chemical Corp Method for the control of insects using thioalkylphenyl carbamates
US3470236A (en) * 1964-06-27 1969-09-30 Bayer Ag Phenyl-n-methyl carbamic acid esters
US3437684A (en) * 1964-07-04 1969-04-08 Bayer Ag 3,5-dimethyl-4-alpha-allyl mercaptophenyl-n-methyl carbamic acid ester
FR2208890A1 (en) * 1972-12-01 1974-06-28 Bayer Ag
WO2002053529A1 (en) * 2000-12-29 2002-07-11 3M Innovative Properties Company High-boiling electrolyte solvent
US6534220B2 (en) 2000-12-29 2003-03-18 3M Innovative Properties Company High-boiling electrolyte solvent
US8846567B2 (en) 2009-03-25 2014-09-30 Bayer Cropscience Ag Active compound combinations having insecticidal and acaricidal properties

Also Published As

Publication number Publication date
NL131470C (en)
BE597806A (en)
CH389314A (en) 1965-03-15
DE1162352B (en) 1964-02-06
BR6024675D0 (en) 1973-06-12
NL258661A (en)

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