GB1138347A - Carbamyl hydroxamate pesticides - Google Patents
Carbamyl hydroxamate pesticidesInfo
- Publication number
- GB1138347A GB1138347A GB5414865A GB5414865A GB1138347A GB 1138347 A GB1138347 A GB 1138347A GB 5414865 A GB5414865 A GB 5414865A GB 5414865 A GB5414865 A GB 5414865A GB 1138347 A GB1138347 A GB 1138347A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- methylcarbamyl
- methyl
- hydroxamate
- prepared
- 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
Links
- VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 title 1
- 239000000575 pesticide Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 13
- -1 methylthio, dimethyl amino Chemical group 0.000 abstract 8
- 150000002148 esters Chemical class 0.000 abstract 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 3
- 125000004414 alkyl thio group Chemical group 0.000 abstract 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 3
- 229910052794 bromium Inorganic materials 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 239000000460 chlorine Chemical group 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 159000000000 sodium salts Chemical class 0.000 abstract 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 abstract 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 abstract 1
- 125000004803 chlorobenzyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 abstract 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 150000003573 thiols Chemical class 0.000 abstract 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
1,138,347. Carbamyl hydroxamates. E. I. DU PONT DE NEMOURS & CO. 21 Dec., 1965, No. 54148/65. Heading C2C. [Also in Divisions A5 and C3] The invention relates to O-carbamyl hydroxamates of the general formula in which R 1 is alkyl of 1 to 12 carbon atoms, haloalkyl of 1 to 12 carbon atoms and 1 to 10 halogen atoms, cycloalkyl of 3 to 10 carbon atoms, benzyl, chlorobenzyl, 1-naphthyl, 2- naphthyl, phenyl, where X is fluorine, chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, cyclohexyl, alkoxy of 1 to 4 carbon atoms, methylthio, dimethyl amino, nitro, cyano, nitroso or trifluoromethyl; Y is H, fluorine, chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or nitro; Z is chlorine, bromine or alkyl of 1 to 4 carbon atoms; and n is 0, 1 or 2; R 2 and R 3 , which can be the same or different, are hydrogen or methyl; and Q is alkylthio of 1 to 12 carbon atoms, phenylthio, p-chlorophenylthio, benzylthio or p-chlorobenzylthio, with the proviso that Q is alkylthio of 1 to 3 carbon atoms when R 1 contains more than 5 carbon atoms. Compounds claimed per se are methyl O - (methylcarbamyl) - p - chloro - thiobenzohydroxamate, methyl O - (dimethylcarbamyl)- thiolacetohydroxamate, sec. - butyl O - (methylcarbamyl) - thiolacetohydroxamate, methyl O- (methylcarbamyl) - p - fluorothiolbenzohydroxamate, methyl-O- (methylcarbamyl)-p-bromothiolbenzohydroxamate, methyl O - (methylcarbamyl) - thiolbutyrohydroxamate, isopropyl O - (methylcarbamyl) - thiodiisobutyrohydroxamate. The O-carbamyl-hydroxamate esters may be prepared by treating a hydroxamate or thiolhydroxamate ester with sodium hydride in tetrahydrofuran, adding the resulting sodium salt to a solution of phosgene, and then treating the chloroformate intermediate with two equivalents of ammonia. The O-methylcarbamyl hydroxamate esters may be prepared by treating a hydroxamate or thiolhydroxamate ester with methyl isocyanate with a small amount of 1,4 - diazabicyclo - [2,2,2] - octane present as a catalyst. The dimethyl compound is prepared by reacting the sodium salt of a thiol hydroxamate ester with dimethylcarbamyl chloride. The thiolhydroxamate ester starting material may be obtained by reacting an imino ether (which may be prepared by reacting a nitrile of formula R 1 CN with a mercaptan of formula QH) with hydroxylamine. They may also be prepared by reacting a hydroxamyl chloride of formula R 1 C(Q)NOH with an alkali metal salt of an alkyl mercaptan of formula QH where Q is alkylthio of 1-12 carbon atoms.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6600273A NL6600273A (en) | 1966-01-10 | 1966-01-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1138347A true GB1138347A (en) | 1969-01-01 |
Family
ID=19795429
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3298968A Expired GB1138348A (en) | 1966-01-10 | 1965-12-21 | Carbamyl hydroxamate pesticides |
| GB5414865A Expired GB1138347A (en) | 1966-01-10 | 1965-12-21 | Carbamyl hydroxamate pesticides |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3298968A Expired GB1138348A (en) | 1966-01-10 | 1965-12-21 | Carbamyl hydroxamate pesticides |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE674792A (en) |
| GB (2) | GB1138348A (en) |
| MY (2) | MY6900404A (en) |
| NL (1) | NL6600273A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4333882A (en) * | 1980-02-18 | 1982-06-08 | Montedison S.P.A. | Process for preparing N-methylcarbamate of methylthioacetaldoxime |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2434184A1 (en) | 1974-07-16 | 1976-02-05 | Bayer Ag | N-SULFENYLATED CARBAMATES, METHOD FOR THEIR PRODUCTION AND USE AS PESTICIDES |
| DE2621102A1 (en) | 1976-05-10 | 1977-11-24 | Schering Ag | PROPANE-1,2-DIONE DIOXIME, SCHAEDLING KINKKKANKAGEN CONTAINING THESE COMPOUNDS AND THE PROCESS FOR THEIR PRODUCTION |
| US4454134A (en) * | 1976-06-14 | 1984-06-12 | Union Carbide Corporation | Amide carbamates and amide oxime compounds |
-
1965
- 1965-12-21 GB GB3298968A patent/GB1138348A/en not_active Expired
- 1965-12-21 GB GB5414865A patent/GB1138347A/en not_active Expired
-
1966
- 1966-01-06 BE BE674792A patent/BE674792A/xx unknown
- 1966-01-10 NL NL6600273A patent/NL6600273A/xx unknown
-
1969
- 1969-12-31 MY MY6900404A patent/MY6900404A/en unknown
- 1969-12-31 MY MY6900409A patent/MY6900409A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4333882A (en) * | 1980-02-18 | 1982-06-08 | Montedison S.P.A. | Process for preparing N-methylcarbamate of methylthioacetaldoxime |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1138348A (en) | 1969-01-01 |
| NL6600273A (en) | 1967-07-11 |
| MY6900409A (en) | 1969-12-31 |
| MY6900404A (en) | 1969-12-31 |
| BE674792A (en) | 1966-05-03 |
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