CA1078870A - N-trichloroacetyl-n'-chlorobenzoylhydrazine derivatives - Google Patents
N-trichloroacetyl-n'-chlorobenzoylhydrazine derivativesInfo
- Publication number
- CA1078870A CA1078870A CA272,953A CA272953A CA1078870A CA 1078870 A CA1078870 A CA 1078870A CA 272953 A CA272953 A CA 272953A CA 1078870 A CA1078870 A CA 1078870A
- Authority
- CA
- Canada
- Prior art keywords
- trichloroacetyl
- chlorobenzoylhydrazine
- following formula
- plants
- fungi
- 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
- 238000000034 method Methods 0.000 claims abstract description 7
- WOVZSCZDJHFSCX-UHFFFAOYSA-N n'-chloro-n-(2,2,2-trichloroacetyl)benzohydrazide Chemical compound ClC(Cl)(Cl)C(=O)N(NCl)C(=O)C1=CC=CC=C1 WOVZSCZDJHFSCX-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 241000233866 Fungi Species 0.000 claims description 9
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 5
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 claims description 5
- -1 benzoic ester Chemical class 0.000 claims description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 2
- SGFCGHYVLVJVMW-UHFFFAOYSA-N 2-chloro-n'-(2,2,2-trichloroacetyl)benzohydrazide Chemical compound ClC1=CC=CC=C1C(=O)NNC(=O)C(Cl)(Cl)Cl SGFCGHYVLVJVMW-UHFFFAOYSA-N 0.000 claims description 2
- ITPFVELWAZEINR-UHFFFAOYSA-N 3-chloro-n'-(2,2,2-trichloroacetyl)benzohydrazide Chemical compound ClC1=CC=CC(C(=O)NNC(=O)C(Cl)(Cl)Cl)=C1 ITPFVELWAZEINR-UHFFFAOYSA-N 0.000 claims description 2
- JQIUHCMAAQLMOY-UHFFFAOYSA-N 4-chloro-n'-(2,2,2-trichloroacetyl)benzohydrazide Chemical compound ClC1=CC=C(C(=O)NNC(=O)C(Cl)(Cl)Cl)C=C1 JQIUHCMAAQLMOY-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000000417 fungicide Substances 0.000 abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 208000015181 infectious disease Diseases 0.000 description 12
- 230000000855 fungicidal effect Effects 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 241000227653 Lycopersicon Species 0.000 description 5
- 241000209094 Oryza Species 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 241000233679 Peronosporaceae Species 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000013505 freshwater Substances 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- VEDIADQJSGNNQE-UHFFFAOYSA-N 3,4-dichlorobenzohydrazide Chemical compound NNC(=O)C1=CC=C(Cl)C(Cl)=C1 VEDIADQJSGNNQE-UHFFFAOYSA-N 0.000 description 1
- PHRDZSRVSVNQRN-UHFFFAOYSA-N 3-chlorobenzohydrazide Chemical compound NNC(=O)C1=CC=CC(Cl)=C1 PHRDZSRVSVNQRN-UHFFFAOYSA-N 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241001281805 Pseudoperonospora cubensis Species 0.000 description 1
- 244000184734 Pyrus japonica Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 101150027734 cript gene Proteins 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- YONQPSPHUKKUEJ-UHFFFAOYSA-N ethyl 3,4-dichlorobenzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C(Cl)=C1 YONQPSPHUKKUEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- OTVVEGIFVPQBPZ-UHFFFAOYSA-N n-acetyl-n'-chlorobenzohydrazide Chemical class CC(=O)N(NCl)C(=O)C1=CC=CC=C1 OTVVEGIFVPQBPZ-UHFFFAOYSA-N 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2281176A JPS52106836A (en) | 1976-03-02 | 1976-03-02 | N-trichloroacetyl-n#-chlorobenzoylhydrazine derivatives and germicide s for agriculture and horticulture containing thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1078870A true CA1078870A (en) | 1980-06-03 |
Family
ID=12093065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA272,953A Expired CA1078870A (en) | 1976-03-02 | 1977-03-01 | N-trichloroacetyl-n'-chlorobenzoylhydrazine derivatives |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4071633A (enExample) |
| JP (1) | JPS52106836A (enExample) |
| CA (1) | CA1078870A (enExample) |
| DE (1) | DE2708886A1 (enExample) |
| ES (1) | ES456359A1 (enExample) |
| FR (1) | FR2342959A1 (enExample) |
| GB (1) | GB1573668A (enExample) |
| NL (1) | NL7702037A (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7711636A (nl) * | 1976-10-28 | 1978-05-03 | Kureha Chemical Ind Co Ltd | Werkwijze voor de bereiding van nieuwe n-gesub- stitueerde en ongesubstitueerd benzoyl-n'-tri- chloorethylideen hydrazine. |
| JPS54141746A (en) * | 1978-04-24 | 1979-11-05 | Kureha Chem Ind Co Ltd | N-benzoyl-n'-halogenoalkylidene hydrazine derivative, its preparation, and agricultural and horticultural fungicide containing the same |
| US4282169A (en) * | 1980-02-19 | 1981-08-04 | Olin Corporation | Selected 2-acyl- or 2-thioacyl-1-trichloroacetimidoylhydrazines and their use as fungicides |
| US5354762A (en) * | 1986-07-14 | 1994-10-11 | Rohm And Haas Company | Six-membered heterocyclic derivatives of N'-substituted N,N'-diacylhydrazines |
| DK483586A (da) * | 1985-10-21 | 1987-04-22 | Rohm & Haas | Insecticide n'-substituerede-n,n'-diacylhydraziner |
| US4985461A (en) * | 1985-10-21 | 1991-01-15 | Rohm And Haas Company | Insecticidal N'-substituted-N,N'-diacylhydrazines |
| US5117057A (en) * | 1985-10-21 | 1992-05-26 | Rohm And Haas Company | Insecticidal N' substituted-N-N'-disubstituted-hydrazines |
| CA1338289C (en) * | 1986-01-22 | 1996-04-30 | Raymond August Murphy | Insecticidal n'-substituted-n-alkylcarbonyl- n'-acylhydrazines |
| TR23119A (tr) * | 1986-01-22 | 1989-04-03 | Rohm & Haas | Ensektisid n-suelostituee n-alkilharbonil-n 1-asil hidrazinler |
| CA1295618C (en) * | 1986-02-28 | 1992-02-11 | Adam Chi-Tung Hsu | Insecticidal n'-substituted-n-acyl -n'-alkylcarbonylhydrazines |
| US5225443A (en) * | 1986-05-01 | 1993-07-06 | Rohm And Haas Company | Insecticidal N'-substituted-N'-substituted N,N'-diacylhydrazines |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE756062A (fr) * | 1969-09-11 | 1971-03-11 | Boehringer Sohn Ingelheim | Derives de 1,1,1-trichlorethane leurs procedes de fabrication et leur utilisation en tant que substances biocides |
| US3660485A (en) * | 1970-10-05 | 1972-05-02 | Searle & Co | Fluorene-9-carboxylic acid hydrazides |
| CH552643A (de) * | 1971-11-26 | 1974-08-15 | Ciba Geigy Ag | Verwendung von diacyl-hydrazine zum stabilisieren von polyolefinen. |
| CH567459A5 (enExample) * | 1972-05-31 | 1975-10-15 | Ciba Geigy Ag |
-
1976
- 1976-03-02 JP JP2281176A patent/JPS52106836A/ja active Pending
-
1977
- 1977-02-25 US US05/772,131 patent/US4071633A/en not_active Expired - Lifetime
- 1977-02-25 NL NL7702037A patent/NL7702037A/xx unknown
- 1977-02-25 DE DE19772708886 patent/DE2708886A1/de not_active Ceased
- 1977-02-28 ES ES456359A patent/ES456359A1/es not_active Expired
- 1977-03-01 FR FR7705942A patent/FR2342959A1/fr active Granted
- 1977-03-01 GB GB8562/77A patent/GB1573668A/en not_active Expired
- 1977-03-01 CA CA272,953A patent/CA1078870A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2342959B1 (enExample) | 1980-10-17 |
| JPS52106836A (en) | 1977-09-07 |
| FR2342959A1 (fr) | 1977-09-30 |
| ES456359A1 (es) | 1978-02-01 |
| NL7702037A (nl) | 1977-09-06 |
| GB1573668A (en) | 1980-08-28 |
| DE2708886A1 (de) | 1977-09-08 |
| US4071633A (en) | 1978-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |