IL23732A - Alkoxy-phenyl-n-methyl carbamic acid esters and a process for their production - Google Patents

Alkoxy-phenyl-n-methyl carbamic acid esters and a process for their production

Info

Publication number: IL23732A
Authority: IL; Israel
Prior art keywords: reaction; process according; general formula; carried out; phosgene
Prior art date: 1964-07-04

Application number

IL23732A

Other languages

English (en)

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.)

1964-07-04

Filing date

1965-06-15

Publication date

1968-11-27

1965-06-15 Application filed by Bayer Ag filed Critical Bayer Ag

1968-11-27 Publication of IL23732A publication Critical patent/IL23732A/en

Links

238000000034 method Methods 0.000 title claims description 23
238000004519 manufacturing process Methods 0.000 title claims description 8
150000001875 compounds Chemical class 0.000 claims description 28
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 12
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 11
-1 chloroformic acid ester Chemical class 0.000 claims description 10
239000012442 inert solvent Substances 0.000 claims description 8
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
241000607479 Yersinia pestis Species 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims description 3
239000000203 mixture Substances 0.000 claims description 3
239000007787 solid Substances 0.000 claims description 3
150000003512 tertiary amines Chemical class 0.000 claims description 2
239000007788 liquid Substances 0.000 claims 2
230000000361 pesticidal effect Effects 0.000 claims 1
239000012429 reaction media Substances 0.000 claims 1
241001465754 Metazoa Species 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
230000000749 insecticidal effect Effects 0.000 description 7
239000000243 solution Substances 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000758 substrate Substances 0.000 description 6
241000255925 Diptera Species 0.000 description 5
150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
230000000694 effects Effects 0.000 description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 4
241000238631 Hexapoda Species 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
239000004927 clay Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000254179 Sitophilus granarius Species 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
238000003197 gene knockdown Methods 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
241000257303 Hymenoptera Species 0.000 description 2
241000257159 Musca domestica Species 0.000 description 2
241000238814 Orthoptera Species 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000000969 carrier Substances 0.000 description 2
229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000008187 granular material Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical class CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000006072 paste Substances 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
238000005507 spraying Methods 0.000 description 2
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
NNZRVXTXKISCGS-UHFFFAOYSA-N 1-methoxy-2-propan-2-ylbenzene Chemical compound COC1=CC=CC=C1C(C)C NNZRVXTXKISCGS-UHFFFAOYSA-N 0.000 description 1
CNTLRGJEUYZYKC-UHFFFAOYSA-N 4-methoxy-3-propan-2-ylphenol Chemical compound COC1=CC=C(O)C=C1C(C)C CNTLRGJEUYZYKC-UHFFFAOYSA-N 0.000 description 1
KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
241000238818 Acheta domesticus Species 0.000 description 1
241000256111 Aedes <genus> Species 0.000 description 1
241000256118 Aedes aegypti Species 0.000 description 1
241001136265 Agriotes Species 0.000 description 1
241001136249 Agriotes lineatus Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
241001124076 Aphididae Species 0.000 description 1
241000238657 Blattella germanica Species 0.000 description 1
241001674044 Blattodea Species 0.000 description 1
241000256593 Brachycaudus schwartzi Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241001465977 Coccoidea Species 0.000 description 1
241000254173 Coleoptera Species 0.000 description 1
241000255601 Drosophila melanogaster Species 0.000 description 1
241000258937 Hemiptera Species 0.000 description 1
241001659689 Hercinothrips Species 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
241000256602 Isoptera Species 0.000 description 1
241000721621 Myzus persicae Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
231100000674 Phytotoxicity Toxicity 0.000 description 1
241000690748 Piesma Species 0.000 description 1
241000500437 Plutella xylostella Species 0.000 description 1
235000005805 Prunus cerasus Nutrition 0.000 description 1
241001509970 Reticulitermes <genus> Species 0.000 description 1
ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 1
241000255588 Tephritidae Species 0.000 description 1
241001414989 Thysanoptera Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000001473 noxious effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
241000894007 species Species 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
- 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

Landscapes

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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

IL23732A 1964-07-04 1965-06-15 Alkoxy-phenyl-n-methyl carbamic acid esters and a process for their production IL23732A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0043354		1964-07-04

Publications (1)

Publication Number	Publication Date
IL23732A true IL23732A (en)	1968-11-27

Family

ID=7099520

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL23732A IL23732A (en)	1964-07-04	1965-06-15	Alkoxy-phenyl-n-methyl carbamic acid esters and a process for their production

Country Status (8)

Country	Link
US (1)	US3433826A (de)
BE (1)	BE666301A (de)
CH (1)	CH462533A (de)
DE (1)	DE1248636B (de)
ES (1)	ES314915A1 (de)
GB (1)	GB1035470A (de)
IL (1)	IL23732A (de)
NL (1)	NL145220B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4303793A (en) *	1979-03-12	1981-12-01	Ppg Industries, Inc.	Aqueous carbamate dispersions

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL254339A (de) *	1959-07-31
DE1143670B (de) *	1961-05-09	1963-02-14	Bayer Ag	Mittel zum Schutz von Materialien gegen Termitenfrass
US3140167A (en) *	1962-06-07	1964-07-07	Hercules Powder Co Ltd	2, 6-di-t-butyl-4-substituted phenyl nu-methyl carbamate and use thereof as selective herbicides

0
- DE DENDAT1248636D patent/DE1248636B/de active Pending
1965
- 1965-06-14 CH CH820765A patent/CH462533A/de unknown
- 1965-06-15 GB GB25234/65A patent/GB1035470A/en not_active Expired
- 1965-06-15 IL IL23732A patent/IL23732A/en unknown
- 1965-06-17 US US464864A patent/US3433826A/en not_active Expired - Lifetime
- 1965-07-02 NL NL656508562A patent/NL145220B/xx unknown
- 1965-07-02 BE BE666301D patent/BE666301A/xx unknown
- 1965-07-03 ES ES0314915A patent/ES314915A1/es not_active Expired

Also Published As

Publication number	Publication date
ES314915A1 (es)	1967-02-01
US3433826A (en)	1969-03-18
BE666301A (de)	1966-01-03
NL145220B (nl)	1975-03-17
DE1248636B (de)	1967-08-31
GB1035470A (en)	1966-07-06
NL6508562A (de)	1966-01-05
CH462533A (de)	1968-09-15

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JPH0629256B2 (ja)	1994-04-20	ニトロメチレン−テトラヒドロピリミジン誘導体，その製法及び殺虫，殺ダニ，殺センチユウ剤
US3674874A (en)	1972-07-04	Insecticidal and acaricidal compositions
US2553777A (en)	1951-05-22	Parasiticidal compositions containing substituted dithiotrichloro methanes
IL30093A (en)	1971-08-25	Phosphoric acid esters,manufacture thereof and their use as insecticides
CA1129856A (en)	1982-08-17	Arthropod repellents
US3470299A (en)	1969-09-30	2-methyl-coumaran-7yl-n-methyl-carbamate
US3950534A (en)	1976-04-13	Fungicidal composition containing 2-(N-n-butylcarbamoylthio) ethyl N1 -n-butyl-thiocarbamate
US3818102A (en)	1974-06-18	Insecticidal sulfonates
KR840001888B1 (ko)	1984-10-24	N-포스포닐카보닐-카바메이트의 제조방법
US3825579A (en)	1974-07-23	N-phenylthiocarbamoylthio-hydroximate pesticides
IL23732A (en)	1968-11-27	Alkoxy-phenyl-n-methyl carbamic acid esters and a process for their production
US3470236A (en)	1969-09-30	Phenyl-n-methyl carbamic acid esters
US3660465A (en)	1972-05-02	Ethynylene containing n-phenyl carbamates
US4038403A (en)	1977-07-26	Benzotriazole ovicides and larvicides
US3437684A (en)	1969-04-08	3,5-dimethyl-4-alpha-allyl mercaptophenyl-n-methyl carbamic acid ester
US4246283A (en)	1981-01-20	Pesticidally active 1-phenyl-1,3,5-triaza-4-sulfa-5-alkylsulfonyl and -phenylsulfonyl-pent-1-en derivatives
US3476490A (en)	1969-11-04	Methods of using particular carbamic acid esters for insecticidal and acaricidal purposes
US3709960A (en)	1973-01-09	O-loweralkyl-o-(2-alkoxylcarbonylmethyl)vinyl-monoalkylamido phosphates
GB1594261A (en)	1981-07-30	Benzyloxime ethers
US3372183A (en)	1968-03-05	Meta-acylphenyl carbamates
US3715436A (en)	1973-02-06	Formimido-esters and pesticidal preparations containing them
US3781331A (en)	1973-12-25	N-trihalomethanesulfenyl-n-methyl-carbamates
US4284626A (en)	1981-08-18	O-aryl S-branched alkyl alkylphosphonodithioate insecticides and nematocides
DE2249939A1 (de)	1974-04-18	Phosphorsaeureester