IL27678A - Pyrimidine containing phosphorus compounds and insecticidal and fungicidal compositions containing them - Google Patents

Pyrimidine containing phosphorus compounds and insecticidal and fungicidal compositions containing them

Info

Publication number: IL27678A
Authority: IL; Israel
Prior art keywords: lower alkyl; hydrogen; compound; pyrimidine; atom
Prior art date: 1966-03-31

Application number

IL27678A

Other languages

English (en)

Original Assignee

Ici Ltd

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.)

1966-03-31

Filing date

1967-03-23

Publication date

1972-07-26

1967-03-23 Application filed by Ici Ltd filed Critical Ici Ltd

1972-07-26 Publication of IL27678A publication Critical patent/IL27678A/en

Links

239000000203 mixture Substances 0.000 title claims description 68
230000000855 fungicidal effect Effects 0.000 title claims description 14
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title claims description 5
230000000749 insecticidal effect Effects 0.000 title claims description 4
150000003018 phosphorus compounds Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 56
125000000217 alkyl group Chemical group 0.000 claims description 34
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 32
239000001257 hydrogen Substances 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 22
150000003230 pyrimidines Chemical class 0.000 claims description 21
-1 alkaline earth metal salt Chemical class 0.000 claims description 20
238000000034 method Methods 0.000 claims description 20
241000238631 Hexapoda Species 0.000 claims description 18
239000004480 active ingredient Substances 0.000 claims description 18
125000004429 atom Chemical group 0.000 claims description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
239000003085 diluting agent Substances 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
206010061217 Infestation Diseases 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 7
241001465754 Metazoa Species 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
239000007788 liquid Substances 0.000 claims description 7
239000000843 powder Substances 0.000 claims description 7
239000000080 wetting agent Substances 0.000 claims description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
239000005864 Sulphur Chemical group 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
239000003337 fertilizer Substances 0.000 claims description 6
239000002689 soil Substances 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
239000007787 solid Substances 0.000 claims description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
239000011230 binding agent Substances 0.000 claims description 4
125000001589 carboacyl group Chemical group 0.000 claims description 4
230000002538 fungal effect Effects 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
239000000463 material Substances 0.000 claims description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
150000007530 organic bases Chemical group 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000005270 trialkylamine group Chemical group 0.000 claims description 2
239000002917 insecticide Substances 0.000 claims 4
239000012429 reaction media Substances 0.000 claims 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 1
125000005265 dialkylamine group Chemical group 0.000 claims 1
229940093499 ethyl acetate Drugs 0.000 claims 1
235000019439 ethyl acetate Nutrition 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
241000196324 Embryophyta Species 0.000 description 14
239000000243 solution Substances 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
239000000725 suspension Substances 0.000 description 8
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239000012141 concentrate Substances 0.000 description 7
239000000839 emulsion Substances 0.000 description 7
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 6
239000003795 chemical substances by application Substances 0.000 description 6
201000010099 disease Diseases 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
230000008341 ER-associated protein catabolic process Effects 0.000 description 5
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235000021307 Triticum Nutrition 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
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 5
239000000047 product Substances 0.000 description 5
239000007921 spray Substances 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000005406 washing Methods 0.000 description 4
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
240000008067 Cucumis sativus Species 0.000 description 3
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
208000031888 Mycoses Diseases 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
241000233626 Plasmopara Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
238000010533 azeotropic distillation Methods 0.000 description 3
239000011575 calcium Substances 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 3
238000010410 dusting Methods 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
RLFMJKKLVIXEAV-UHFFFAOYSA-N methoxysulfinylphosphonic acid Chemical compound COS(=O)P(O)(O)=O RLFMJKKLVIXEAV-UHFFFAOYSA-N 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
238000005507 spraying Methods 0.000 description 3
FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
241000256111 Aedes <genus> Species 0.000 description 2
241001124076 Aphididae Species 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
241000255925 Diptera Species 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
240000005979 Hordeum vulgare Species 0.000 description 2
235000007340 Hordeum vulgare Nutrition 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
241000721715 Macrosiphum Species 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
241000498271 Necator Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
240000003768 Solanum lycopersicum Species 0.000 description 2
229920001938 Vegetable gum Polymers 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
239000000440 bentonite Substances 0.000 description 2
229910000278 bentonite Inorganic materials 0.000 description 2
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
210000000234 capsid Anatomy 0.000 description 2
239000000969 carrier Substances 0.000 description 2
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238000010790 dilution Methods 0.000 description 2
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239000002270 dispersing agent Substances 0.000 description 2
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150000002148 esters Chemical class 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
150000002466 imines Chemical class 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
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229910000027 potassium carbonate Inorganic materials 0.000 description 2
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UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
CBQDTCDOVVBGMN-UHFFFAOYSA-N 2-methyl-3-octylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1C CBQDTCDOVVBGMN-UHFFFAOYSA-N 0.000 description 1
AWTRFGBAOOYGSF-UHFFFAOYSA-N 2-morpholin-4-yl-6-phenyl-1h-pyrimidin-4-one Chemical compound N=1C(=O)C=C(C=2C=CC=CC=2)NC=1N1CCOCC1 AWTRFGBAOOYGSF-UHFFFAOYSA-N 0.000 description 1
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235000019198 oils Nutrition 0.000 description 1
239000002674 ointment Substances 0.000 description 1
125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000003380 propellant Substances 0.000 description 1
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical class NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
229910052911 sodium silicate Inorganic materials 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
238000010998 test method Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
150000003738 xylenes Chemical class 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
- 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
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon 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)
Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agronomy & Crop Science (AREA)
Organic Chemistry (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

IL27678A 1966-03-31 1967-03-23 Pyrimidine containing phosphorus compounds and insecticidal and fungicidal compositions containing them IL27678A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB1426966		1966-03-31
GB1426766		1966-03-31
GB14268/66A GB1129563A (en)	1966-03-31	1966-03-31	Phosphorus-containing pyrimidine derivatives and biologically active compositions containing them
GB14266/66A GB1129797A (en)	1966-03-31	1966-03-31	Phosphorus-containing pyrimidine derivatives and biologically active compositions containing them

Publications (1)

Publication Number	Publication Date
IL27678A true IL27678A (en)	1972-07-26

Family

ID=35530797

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL27678A IL27678A (en)	1966-03-31	1967-03-23	Pyrimidine containing phosphorus compounds and insecticidal and fungicidal compositions containing them

Country Status (7)

Country	Link
US (1)	US4041157A (xx)
BE (2)	BE696468A (xx)
DE (2)	DE1695271B2 (xx)
FR (2)	FR1548279A (xx)
GB (2)	GB1129563A (xx)
IL (1)	IL27678A (xx)
NL (2)	NL6704603A (xx)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1388401A (en) *	1971-05-06	1975-03-26	Ici Ltd	Pesticidal pyrimidinyl esters of phosphorus acids
GB1390282A (en) *	1972-12-18	1975-04-09	Ici Ltd	Phosphorus-containing pyrimidine derivatives
GB1441206A (en) *	1974-05-20	1976-06-30	Ici Ltd	Process for preparing 2-amino-4-hydroxypyrimidine derivatives
DE2619450A1 (de) *	1976-05-03	1977-11-24	Bayer Ag	Diphosphorylierte pyrimidine, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
DE2620089A1 (de) *	1976-05-06	1977-11-24	Bayer Ag	Substituierte pyrimidin-bis- eckige klammer auf (thiono)(thiol)-phosphor(phosphon)-saeureester eckige klammer zu, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide
US4892732A (en) *	1987-11-27	1990-01-09	The Dow Chemical Company	Method and composition for enhancing the insecticidal activity of certain organophosphorus compounds
WO2003000186A2 (en)	2001-06-21	2003-01-03	Ariad Pharmaceuticals, Inc.	Novel phenylamino-pyrimidines and uses thereof
ES2645689T3 (es)	2008-05-21	2017-12-07	Ariad Pharmaceuticals, Inc.	Derivados de fósforo como inhibidores de quinasas
US9273077B2 (en)	2008-05-21	2016-03-01	Ariad Pharmaceuticals, Inc.	Phosphorus derivatives as kinase inhibitors
EA201391626A1 (ru)	2011-05-04	2014-03-31	Ариад Фармасьютикалз, Инк.	Соединения для ингибирования клеточной пролиферации в egfr-стимулированных типах рака
AU2013204563B2 (en)	2012-05-05	2016-05-19	Takeda Pharmaceutical Company Limited	Compounds for inhibiting cell proliferation in EGFR-driven cancers
US9611283B1 (en)	2013-04-10	2017-04-04	Ariad Pharmaceuticals, Inc.	Methods for inhibiting cell proliferation in ALK-driven cancers

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL129225C (xx) *	1963-03-28	1900-01-01
US3906094A (en) *	1966-03-31	1975-09-16	Ici Ltd	Method and composition for combatting fungus with fungicidally-active pyrimidine derivatives
US3651224A (en) *	1967-09-21	1972-03-21	Ici Ltd	Pesticidal pyrimidine derivative
GB1257634A (xx) *	1968-08-07	1971-12-22

1966
- 1966-03-31 GB GB14268/66A patent/GB1129563A/en not_active Expired
- 1966-03-31 GB GB14266/66A patent/GB1129797A/en not_active Expired
1967
- 1967-03-23 IL IL27678A patent/IL27678A/en unknown
- 1967-03-28 DE DE1967J0033313 patent/DE1695271B2/de active Granted
- 1967-03-29 DE DE1695273A patent/DE1695273C3/de not_active Expired
- 1967-03-31 BE BE696468D patent/BE696468A/xx unknown
- 1967-03-31 FR FR1548279D patent/FR1548279A/fr not_active Expired
- 1967-03-31 NL NL6704603A patent/NL6704603A/xx not_active Application Discontinuation
- 1967-03-31 BE BE696467D patent/BE696467A/xx unknown
- 1967-03-31 FR FR1548278D patent/FR1548278A/fr not_active Expired
- 1967-03-31 NL NL6704665A patent/NL6704665A/xx not_active Application Discontinuation
1975
- 1975-08-27 US US05/608,331 patent/US4041157A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DE1695271B2 (de)	1976-12-09
FR1548279A (xx)	1968-12-06
DE1695273A1 (de)	1971-06-03
GB1129563A (en)	1968-10-09
FR1548278A (xx)	1968-12-06
NL6704665A (xx)	1967-10-02
NL6704603A (xx)	1967-10-02
DE1695271A1 (de)	1971-06-03
BE696467A (xx)	1967-10-02
GB1129797A (en)	1968-10-09
US4041157A (en)	1977-08-09
BE696468A (xx)	1967-10-02
DE1695273B2 (de)	1977-10-27
DE1695273C3 (de)	1978-06-29

Publication	Publication Date	Title
US3577543A (en)	1971-05-04	Insecticidal and fungicidal 2-aminopyrimidinyl-6-carbamate compositions
IL27678A (en)	1972-07-26	Pyrimidine containing phosphorus compounds and insecticidal and fungicidal compositions containing them
EP0335519A1 (en)	1989-10-04	Insecticides
EP0194311A1 (en)	1986-09-17	1-IODOPROPARGYL-3,4-DISUBSTITUTED-$g(D)?2 -1,2,4-TRIAZOLIDIN-5-ONE FUNGICIDES
US3657247A (en)	1972-04-18	Pesticidal halogen-substituted pyrimidinyl phosphorus esters
US3930835A (en)	1976-01-06	Pesticidal compositions and methods employing substituted oxirane compounds
US3828043A (en)	1974-08-06	5-acyl barbituric acid derivatives
US4444764A (en)	1984-04-24	Phosphorus esters of alkylcycloalkyl-5-pyrimidinols and control of corn rootworm and western spotted cucumber beetle with them
US3906094A (en)	1975-09-16	Method and composition for combatting fungus with fungicidally-active pyrimidine derivatives
US4172080A (en)	1979-10-23	Phosphorus esters of 1-cyanoethyl-1,2,4-triazol-3-ols
US5089510A (en)	1992-02-18	Insecticides
EP0023841B1 (en)	1984-03-21	5 pyrimidinol phosphorus esters, and methods for their manufacture, compositions containing those esters and their use as pesticides
US3932631A (en)	1976-01-13	Certain organophosphorus compounds used to control insects
US3674877A (en)	1972-07-04	Pesticidally active compounds and compositions containing them
US3784546A (en)	1974-01-08	O(2-diethylamino-4-methyl-6-primidinyl)o,o-dimethyl phosphorothioate and its salts
US3622578A (en)	1971-11-23	Substituted s-((4-oxo-1,2,3-benzotriazin-3(4h)-yl)methyl) phosphorothioates and phosphorodithioates
US4302240A (en)	1981-11-24	Alkyl (mono-, di, tri- and tetra-thio)phosphorylated isothiazolidin-3-one 1-oxides and 1,1-dioxides
EP0081945B1 (en)	1986-09-03	Substituted pyrimidinyl organophosphorus compounds, compositions thereof and methods of controlling pests
EP0065287A2 (en)	1982-11-24	N-containing heterocyclic ring-substituted O-arylphosphate derivatives, preparation thereof, and insecticides containing said derivatives
US3502670A (en)	1970-03-24	S-((4-oxo - 1,2,3-benzotriazin-3(4h)-yl)-methyl) phosphorothioates and phosphorodithioates
US3551562A (en)	1970-12-29	Insecticidal use of s-((4-oxo-1,2,3-benzotriazin - 3(4h)-yl) - methyl) phosphorothioates and phosphorodithioates
GB2039487A (en)	1980-08-13	New fungicidal derivatives of N- phenyl-N-(alkoxycarbonylalkyl) -acetamide phosphorodithioates
IL27679A (en)	1972-05-30	Pyrimidine containing phosphates and thiophosphates and insecticidal and fungicidal compositions containing them
US4472389A (en)	1984-09-18	Substituted pyrimidinyl organophosphorus insecticides
US4439430A (en)	1984-03-27	O,O-Diethyl O-[(p-tertiarybutylthio)phenyl]phosphorothioates and its insecticidal use