IL28893A - N-carbamoyloxy-iminocyanoacetic acid derivatives,their manufacture and pesticidal compositions containing them - Google Patents
N-carbamoyloxy-iminocyanoacetic acid derivatives,their manufacture and pesticidal compositions containing themInfo
- Publication number
- IL28893A IL28893A IL28893A IL2889367A IL28893A IL 28893 A IL28893 A IL 28893A IL 28893 A IL28893 A IL 28893A IL 2889367 A IL2889367 A IL 2889367A IL 28893 A IL28893 A IL 28893A
- Authority
- IL
- Israel
- Prior art keywords
- carbamate
- preparation
- formula
- active ingredient
- pesticidal
- Prior art date
Links
- 230000000361 pesticidal effect Effects 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000000203 mixture Substances 0.000 title description 7
- 239000002253 acid Substances 0.000 title description 3
- 238000002360 preparation method Methods 0.000 claims description 19
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- -1 N-phenylamino Chemical group 0.000 claims description 6
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims 4
- 244000052616 bacterial pathogen Species 0.000 claims 3
- 244000053095 fungal pathogen Species 0.000 claims 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 101100497505 Mus musculus Ctnnd1 gene Proteins 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 239000007767 bonding agent Substances 0.000 claims 1
- 150000001714 carbamic acid halides Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000002562 thickening agent Substances 0.000 claims 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000155 melt Substances 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 4
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000003032 phytopathogenic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 241001533598 Septoria Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 1
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000749 insecticidal effect Effects 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1625966A CH484604A (de) | 1966-11-10 | 1966-11-10 | Schädlingsbekämpfungsmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL28893A true IL28893A (en) | 1971-12-29 |
Family
ID=4415767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL28893A IL28893A (en) | 1966-11-10 | 1967-11-06 | N-carbamoyloxy-iminocyanoacetic acid derivatives,their manufacture and pesticidal compositions containing them |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US3625987A (de) |
| AT (1) | AT283048B (de) |
| BE (1) | BE706291A (de) |
| BG (1) | BG16725A3 (de) |
| CA (1) | CA931148A (de) |
| CH (1) | CH484604A (de) |
| CS (1) | CS164248B2 (de) |
| DE (1) | DE1693052A1 (de) |
| GB (1) | GB1191468A (de) |
| IL (1) | IL28893A (de) |
| IT (1) | IT954017B (de) |
| SE (1) | SE339462B (de) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH496395A (de) * | 1968-07-24 | 1970-09-30 | Agripat Sa | Schädlingsbekämpfungsmittel |
| ZA731111B (en) * | 1972-03-15 | 1974-03-27 | Du Pont | 2-cyano-2-hydroxyiminoacetamides and acetates as plant disease control agents |
| JPS5541227B2 (de) * | 1972-10-24 | 1980-10-22 | ||
| US3984568A (en) * | 1975-09-11 | 1976-10-05 | E. I. Du Pont De Nemours And Company | Fungicidal cyclopropyl substituted 2-cyanoacetamide derivatives |
| US3979518A (en) * | 1975-09-11 | 1976-09-07 | E. I. Du Pont De Nemours And Company | Fungicidal alkoxy substituted 2-cyanoacetamide derivatives |
| US3954992A (en) * | 1973-07-02 | 1976-05-04 | E. I. Du Pont De Nemours And Company | 2-Cyano-2-hydroxyiminoacetamides as plant disease control agents |
| ZA751269B (en) * | 1974-03-21 | 1976-01-28 | Du Pont | N-carbamoyl-2-cyano-2-oxyiminoacetamines as plant disease control agents |
| US4063921A (en) * | 1973-10-09 | 1977-12-20 | Ciba-Geigy Corporation | Method for the cultivation of plants employing α-cyano-α-hydroxyimino-acetamide derivatives |
| US3957847A (en) * | 1974-03-21 | 1976-05-18 | E. I. Du Pont De Nemours And Company | 2-cyano-2-hydroxyiminoacetamides as plant disease control agents |
| US3919284A (en) * | 1974-06-13 | 1975-11-11 | Du Pont | Process for making 2-cyano-2-hydroxyiminoacetamide salts |
| US4029688A (en) * | 1974-06-27 | 1977-06-14 | Union Carbide Corporation | Carbamic pesticidal compositions |
| DE2626828A1 (de) * | 1976-06-15 | 1977-12-22 | Bayer Ag | Neue carbamidsaeureoximester, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| US4188401A (en) | 1977-06-04 | 1980-02-12 | Bayer Aktiengesellschaft | Combating fungi with 1-(ω-substituted pentyl)-3-(2-cyano-acetyl)-ureas |
| US5192638A (en) * | 1984-12-10 | 1993-03-09 | Spectrum Sciences B.V. | Toner for use in compositions for developing latent electrostatic images, method of making the same, and liquid composition using the improved toner |
| IL99078A0 (en) * | 1990-08-06 | 1992-07-15 | Du Pont | Bis-(hydroximidoyl chloride)derivatives,fungicidal compositions containing them and their use as fungicides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2925434A (en) * | 1956-03-06 | 1960-02-16 | Charles O Parker | Dinitrocyanoacetates |
| US3256330A (en) * | 1961-09-22 | 1966-06-14 | Union Carbide Corp | Cyclohexenone n-alkylcarbamyloximes |
| US3466316A (en) * | 1964-09-23 | 1969-09-09 | Union Carbide Corp | Alpha-cyano carbamoyloxime compounds |
| US3328457A (en) * | 1964-12-14 | 1967-06-27 | Union Carbide Corp | Carbamoyloxime |
-
1966
- 1966-11-10 CH CH1625966A patent/CH484604A/de not_active IP Right Cessation
-
1967
- 1967-11-02 DE DE19671693052 patent/DE1693052A1/de active Pending
- 1967-11-02 BG BG8831A patent/BG16725A3/xx unknown
- 1967-11-06 IL IL28893A patent/IL28893A/en unknown
- 1967-11-07 CA CA004440A patent/CA931148A/en not_active Expired
- 1967-11-07 US US681101A patent/US3625987A/en not_active Expired - Lifetime
- 1967-11-08 GB GB50869/67A patent/GB1191468A/en not_active Expired
- 1967-11-08 IT IT40557/67A patent/IT954017B/it active
- 1967-11-08 CS CS7920A patent/CS164248B2/cs unknown
- 1967-11-09 AT AT1008967A patent/AT283048B/de not_active IP Right Cessation
- 1967-11-09 SE SE15373/67A patent/SE339462B/xx unknown
- 1967-11-09 BE BE706291D patent/BE706291A/xx unknown
-
1971
- 1971-05-26 US US00147192A patent/US3769423A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US3625987A (en) | 1971-12-07 |
| DE1693052A1 (de) | 1971-05-13 |
| CA931148A (en) | 1973-07-31 |
| SE339462B (de) | 1971-10-11 |
| CH484604A (de) | 1970-01-31 |
| IT954017B (it) | 1973-08-30 |
| BG16725A3 (de) | 1973-02-15 |
| BE706291A (de) | 1968-05-09 |
| GB1191468A (en) | 1970-05-13 |
| US3769423A (en) | 1973-10-30 |
| CS164248B2 (de) | 1975-11-07 |
| AT283048B (de) | 1970-07-27 |
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