CA1047497A - Heterocyclic derivative - Google Patents
Heterocyclic derivativeInfo
- Publication number
- CA1047497A CA1047497A CA200,703A CA200703A CA1047497A CA 1047497 A CA1047497 A CA 1047497A CA 200703 A CA200703 A CA 200703A CA 1047497 A CA1047497 A CA 1047497A
- Authority
- CA
- Canada
- Prior art keywords
- phosphorothionate
- diethylaminopyrimidin
- pests
- compound
- dimethyl
- 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
- 125000000623 heterocyclic group Chemical group 0.000 title 1
- 241000607479 Yersinia pestis Species 0.000 claims description 20
- 241000238631 Hexapoda Species 0.000 claims description 5
- 239000000203 mixture Substances 0.000 abstract description 17
- 230000000361 pesticidal effect Effects 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 description 19
- 239000004480 active ingredient Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241001608567 Phaedon cochleariae Species 0.000 description 6
- 241000255969 Pieris brassicae Species 0.000 description 6
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- -1 2-diethylaminopyrimidin-4-yl Chemical group 0.000 description 4
- 241000219198 Brassica Species 0.000 description 4
- 235000003351 Brassica cretica Nutrition 0.000 description 4
- 235000003343 Brassica rupestris Nutrition 0.000 description 4
- 241000500437 Plutella xylostella Species 0.000 description 4
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 235000010460 mustard Nutrition 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 241000256118 Aedes aegypti Species 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 239000008262 pumice Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- ZRVKDGHDCOMYDX-UHFFFAOYSA-N 2-(diethylamino)-1h-pyrimidin-6-one Chemical compound CCN(CC)C1=NC=CC(=O)N1 ZRVKDGHDCOMYDX-UHFFFAOYSA-N 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000171274 Megoura Species 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- 241000257226 Muscidae Species 0.000 description 2
- 241000131102 Oryzaephilus Species 0.000 description 2
- 241000254179 Sitophilus granarius Species 0.000 description 2
- 241000344246 Tetranychus cinnabarinus Species 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- XFBJRFNXPUCPKU-UHFFFAOYSA-N chloro-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound COP(Cl)(=S)OC XFBJRFNXPUCPKU-UHFFFAOYSA-N 0.000 description 2
- 229910003460 diamond Inorganic materials 0.000 description 2
- 239000010432 diamond Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000011120 plywood Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- HAEVLZUBSLBWIX-UHFFFAOYSA-N 2-octylphenol;oxirane Chemical compound C1CO1.CCCCCCCCC1=CC=CC=C1O HAEVLZUBSLBWIX-UHFFFAOYSA-N 0.000 description 1
- 241000256111 Aedes <genus> Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241000256113 Culicidae Species 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241001127120 Dysdercus fasciatus Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000243786 Meloidogyne incognita Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241000257229 Musca <genus> Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241000254112 Tribolium confusum Species 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- 210000000234 capsid Anatomy 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 238000009736 wetting Methods 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2655573A GB1434764A (en) | 1973-06-04 | 1973-06-04 | Pesticidal phosphorus-containing pyrimidine derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1047497A true CA1047497A (en) | 1979-01-30 |
Family
ID=10245485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA200,703A Expired CA1047497A (en) | 1973-06-04 | 1974-05-23 | Heterocyclic derivative |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5031049A (enrdf_load_stackoverflow) |
| CA (1) | CA1047497A (enrdf_load_stackoverflow) |
| CH (1) | CH585017A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2426609A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2231680B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1434764A (enrdf_load_stackoverflow) |
| IL (1) | IL44847A (enrdf_load_stackoverflow) |
| IT (1) | IT1046645B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5832226B2 (ja) * | 1977-01-18 | 1983-07-12 | 三菱マテリアル株式会社 | ビット用炭化タングステン基超硬合金 |
| JPH116025A (ja) * | 1997-04-25 | 1999-01-12 | Sumitomo Electric Ind Ltd | 超硬合金と、この超硬合金を母材とする被覆合金および被覆硬質工具 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL129225C (enrdf_load_stackoverflow) * | 1963-03-28 | 1900-01-01 |
-
1973
- 1973-06-04 GB GB2655573A patent/GB1434764A/en not_active Expired
-
1974
- 1974-05-16 IL IL44847A patent/IL44847A/en unknown
- 1974-05-23 CA CA200,703A patent/CA1047497A/en not_active Expired
- 1974-05-28 IT IT23279/74A patent/IT1046645B/it active
- 1974-05-31 FR FR7418925A patent/FR2231680B1/fr not_active Expired
- 1974-05-31 DE DE19742426609 patent/DE2426609A1/de not_active Withdrawn
- 1974-06-03 JP JP49061958A patent/JPS5031049A/ja active Pending
- 1974-06-04 CH CH758274A patent/CH585017A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL44847A (en) | 1976-10-31 |
| DE2426609A1 (de) | 1975-01-02 |
| FR2231680A1 (enrdf_load_stackoverflow) | 1974-12-27 |
| IL44847A0 (en) | 1974-07-31 |
| FR2231680B1 (enrdf_load_stackoverflow) | 1978-01-20 |
| AU6889874A (en) | 1975-11-20 |
| IT1046645B (it) | 1980-07-31 |
| JPS5031049A (enrdf_load_stackoverflow) | 1975-03-27 |
| CH585017A5 (enrdf_load_stackoverflow) | 1977-02-28 |
| GB1434764A (en) | 1976-05-05 |
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