IL43034A - Phosphorus-containing esters of condensed ring pyrimidine derivatives,process for their preparation and compositions containing them - Google Patents

Phosphorus-containing esters of condensed ring pyrimidine derivatives,process for their preparation and compositions containing them

Info

Publication number: IL43034A
Authority: IL; Israel
Prior art keywords: carbon atoms; formula; radical; compound; kyl
Prior art date: 1972-09-11

Application number

IL43034A

Other languages

English (en)

Other versions

IL43034A0 (en

Original Assignee

Roussel Uclaf

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.)

1972-09-11

Filing date

1973-08-21

Publication date

1976-05-31

1973-08-21 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1973-11-28 Publication of IL43034A0 publication Critical patent/IL43034A0/xx

1976-05-31 Publication of IL43034A publication Critical patent/IL43034A/en

Links

239000000203 mixture Substances 0.000 title claims description 24
238000000034 method Methods 0.000 title description 4
150000002148 esters Chemical class 0.000 title description 3
238000002360 preparation method Methods 0.000 title description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title 1
229910052698 phosphorus Inorganic materials 0.000 title 1
239000011574 phosphorus Substances 0.000 title 1
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
150000003230 pyrimidines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 30
LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 claims description 21
230000000749 insecticidal effect Effects 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 11
230000001069 nematicidal effect Effects 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
239000011149 active material Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
230000000361 pesticidal effect Effects 0.000 claims description 4
SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims description 3
239000000463 material Substances 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
238000004519 manufacturing process Methods 0.000 claims 2
229910052757 nitrogen Inorganic materials 0.000 claims 2
125000004433 nitrogen atom Chemical group N* 0.000 claims 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 31
239000000047 product Substances 0.000 description 15
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
239000013078 crystal Substances 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
238000011282 treatment Methods 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
-1 halogeno phosphate Chemical compound 0.000 description 10
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 9
238000001704 evaporation Methods 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
241000238631 Hexapoda Species 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
VFMCUTPRJLZEEW-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrimidine Chemical compound C1=CC=CN2CC=CN=C21 VFMCUTPRJLZEEW-UHFFFAOYSA-N 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
230000000895 acaricidal effect Effects 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
229910052500 inorganic mineral Inorganic materials 0.000 description 5
239000011707 mineral Substances 0.000 description 5
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 5
239000002689 soil Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 4
229940126062 Compound A Drugs 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 0.000 description 4
235000013601 eggs Nutrition 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
241001425390 Aphis fabae Species 0.000 description 3
241001635274 Cydia pomonella Species 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
244000141359 Malus pumila Species 0.000 description 3
244000046052 Phaseolus vulgaris Species 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000005507 spraying Methods 0.000 description 3
241001674044 Blattodea Species 0.000 description 2
NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 2
241000255601 Drosophila melanogaster Species 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000257159 Musca domestica Species 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
241000786363 Rhampholeon spectrum Species 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
241000985245 Spodoptera litura Species 0.000 description 2
241000254112 Tribolium confusum Species 0.000 description 2
239000002253 acid Substances 0.000 description 2
235000021016 apples Nutrition 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000037406 food intake Effects 0.000 description 2
239000003292 glue Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
XGGMTLLYGOPCKR-UHFFFAOYSA-N 3-oxo-3-(2,3,4-trichlorophenoxy)propanoic acid Chemical compound OC(=O)CC(=O)OC1=CC=C(Cl)C(Cl)=C1Cl XGGMTLLYGOPCKR-UHFFFAOYSA-N 0.000 description 1
YSYSCJKUUFTREM-UHFFFAOYSA-N 6h-pyrimido[1,2-a]pyrimidine Chemical compound N1=CC=CN2CC=CN=C21 YSYSCJKUUFTREM-UHFFFAOYSA-N 0.000 description 1
VFTOHJFKIJLYKN-UHFFFAOYSA-N 7-nitro-9h-fluoren-2-ol Chemical group [O-][N+](=O)C1=CC=C2C3=CC=C(O)C=C3CC2=C1 VFTOHJFKIJLYKN-UHFFFAOYSA-N 0.000 description 1
JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
241000238876 Acari Species 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241000255579 Ceratitis capitata Species 0.000 description 1
241000255581 Drosophila <fruit fly, genus> Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
240000008415 Lactuca sativa Species 0.000 description 1
235000003228 Lactuca sativa Nutrition 0.000 description 1
241001608711 Melo Species 0.000 description 1
241001143352 Meloidogyne Species 0.000 description 1
241001585712 Noctua Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
241000254179 Sitophilus granarius Species 0.000 description 1
240000003768 Solanum lycopersicum Species 0.000 description 1
241001454293 Tetranychus urticae Species 0.000 description 1
240000006677 Vicia faba Species 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000005005 aminopyrimidines Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
AMZONRRFUQKTSZ-UHFFFAOYSA-N benzene;2-propan-2-yloxypropane Chemical compound C1=CC=CC=C1.CC(C)OC(C)C AMZONRRFUQKTSZ-UHFFFAOYSA-N 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
210000000038 chest Anatomy 0.000 description 1
ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
229910052919 magnesium silicate Inorganic materials 0.000 description 1
235000019792 magnesium silicate Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
231100000194 ovacidal Toxicity 0.000 description 1
230000003151 ovacidal effect Effects 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
AGZPNUZBDCYTBB-UHFFFAOYSA-N triethyl methanetricarboxylate Chemical compound CCOC(=O)C(C(=O)OCC)C(=O)OCC AGZPNUZBDCYTBB-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

IL43034A 1972-09-11 1973-08-21 Phosphorus-containing esters of condensed ring pyrimidine derivatives,process for their preparation and compositions containing them IL43034A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7232088A FR2198697B1 (xx)	1972-09-11	1972-09-11

Publications (2)

Publication Number	Publication Date
IL43034A0 IL43034A0 (en)	1973-11-28
IL43034A true IL43034A (en)	1976-05-31

Family

ID=9104093

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL43034A IL43034A (en)	1972-09-11	1973-08-21	Phosphorus-containing esters of condensed ring pyrimidine derivatives,process for their preparation and compositions containing them

Country Status (20)

Country	Link
US (1)	US3904624A (xx)
JP (1)	JPS5648481B2 (xx)
BE (1)	BE804654A (xx)
BR (1)	BR7306999D0 (xx)
CH (1)	CH575430A5 (xx)
DD (1)	DD109316A5 (xx)
DK (1)	DK138899B (xx)
ES (1)	ES418627A1 (xx)
FR (1)	FR2198697B1 (xx)
GB (1)	GB1408718A (xx)
GT (1)	GT198065690A (xx)
HU (1)	HU168852B (xx)
IL (1)	IL43034A (xx)
IT (1)	IT1047946B (xx)
NL (1)	NL7312432A (xx)
OA (1)	OA04553A (xx)
SU (2)	SU507246A3 (xx)
TR (1)	TR18108A (xx)
YU (1)	YU36304B (xx)
ZA (1)	ZA735709B (xx)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2703712A1 (de) *	1977-01-29	1978-08-03	Bayer Ag	Substituierte pyrimidinon eckige klammer auf (di)-thio eckige klammer zu -phosphor-(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide
US4472389A (en) *	1981-12-10	1984-09-18	Uniroyal, Inc.	Substituted pyrimidinyl organophosphorus insecticides
US4395551A (en) *	1981-12-10	1983-07-26	Uniroyal, Inc.	Pyridopyrimidinone compounds
US4634690A (en) *	1981-12-10	1987-01-06	Uniroyal Chemical Company, Inc.	Substituted pyrimidinyl organophosphorus insecticides
JPS60125077U (ja) *	1984-01-30	1985-08-23	織田　義男	釘打用支持具
JP2532677Y2 (ja) *	1991-03-13	1997-04-16	株式会社日本バノック	固縛具
US5508281A (en) *	1991-04-08	1996-04-16	Duquesne University Of The Holy Ghost	Derivatives of pyrido [2,3-d] and [3,2-d] pyrimidine and methods of using these derivatives
US5939420A (en) *	1991-04-08	1999-08-17	Duquesne University Of The Holy Ghost	Pyrrolo 2,3d!derivatives
US5877178A (en)	1991-04-08	1999-03-02	Duquesne University Of The Holy Ghost	Pyrimidine derivatives and methods of making and using these derivatives
WO1992017478A1 (en) *	1991-04-08	1992-10-15	Duquesne University Of The Holy Ghost	5-ALKYL-6-[[AMINO]METHYL]PYRIDO[2,3-d]PYRIMIDINE DERIVATIVES AND METHODS OF PREPARING AND USING THESE DERIVATIVES
US5346900A (en) *	1991-04-08	1994-09-13	Duquesne University Of The Holy Ghost	5-alkyl-6-[[amino]methyl]pyrido[2,3-D]pyrimidine derivatives and methods of using these derivatives
US6962920B2 (en)	1992-09-23	2005-11-08	Duquesne University Of The Holy Ghost	Pyrimidine derivatives and methods of making and using these derivatives
US6537999B2 (en)	1996-06-06	2003-03-25	Duquesne University Of The Holy Ghost	Pyrimidine derivatives and methods of making and using these derivatives
US6106033A (en) *	1997-08-26	2000-08-22	Ewald Witte Gmbh & Co. Kg	Catch-hook arrangement for a front hood or the like on motor vehicles
JP6250656B2 (ja) *	2012-06-19	2017-12-20	ダウグローバルテクノロジーズエルエルシー	水含有システムにおける抗微生物用複素環式化合物の使用

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1239695B (de) *	1964-12-24	1967-05-03	Bayer Ag	Verfahren zur Herstellung von Phosphor-, Phosphon-, Thionophosphor- oder Thiono-phosphonsaeureestern
BE788828A (fr) *	1971-09-16	1973-03-14	Roussel Uclaf	Nouveaux derives organophosphores heterocycliques et procede depreparation

1972
- 1972-09-11 FR FR7232088A patent/FR2198697B1/fr not_active Expired
1973
- 1973-08-15 DD DD172908A patent/DD109316A5/xx unknown
- 1973-08-21 IL IL43034A patent/IL43034A/en unknown
- 1973-08-21 ZA ZA735709A patent/ZA735709B/xx unknown
- 1973-09-04 US US394078A patent/US3904624A/en not_active Expired - Lifetime
- 1973-09-10 YU YU2404/73A patent/YU36304B/xx unknown
- 1973-09-10 BE BE135484A patent/BE804654A/xx not_active IP Right Cessation
- 1973-09-10 BR BR6999/73A patent/BR7306999D0/pt unknown
- 1973-09-10 NL NL7312432A patent/NL7312432A/xx active Search and Examination
- 1973-09-10 ES ES418627A patent/ES418627A1/es not_active Expired
- 1973-09-10 IT IT52424/73A patent/IT1047946B/it active
- 1973-09-10 SU SU1956353A patent/SU507246A3/ru active
- 1973-09-10 CH CH1293873A patent/CH575430A5/xx not_active IP Right Cessation
- 1973-09-11 TR TR18108A patent/TR18108A/xx unknown
- 1973-09-11 HU HURO749A patent/HU168852B/hu unknown
- 1973-09-11 GB GB4259273A patent/GB1408718A/en not_active Expired
- 1973-09-11 JP JP10175773A patent/JPS5648481B2/ja not_active Expired
- 1973-09-11 DK DK497773AA patent/DK138899B/da unknown
- 1973-09-11 OA OA55010A patent/OA04553A/xx unknown
1976
- 1976-03-04 SU SU762329602A patent/SU733504A3/ru active
1980
- 1980-10-03 GT GT198065690A patent/GT198065690A/es unknown

Also Published As

Publication number	Publication date
DE2345762B2 (de)	1977-04-21
ZA735709B (en)	1974-10-30
JPS4992096A (xx)	1974-09-03
NL7312432A (xx)	1974-03-13
GB1408718A (en)	1975-10-01
GT198065690A (es)	1982-03-27
HU168852B (xx)	1976-07-28
JPS5648481B2 (xx)	1981-11-16
YU240473A (en)	1981-08-31
DK138899B (da)	1978-11-13
SU507246A3 (ru)	1976-03-15
FR2198697A1 (xx)	1974-04-05
IL43034A0 (en)	1973-11-28
DK138899C (xx)	1979-04-23
YU36304B (en)	1982-06-18
DE2345762A1 (de)	1974-03-21
BE804654A (fr)	1974-03-11
DD109316A5 (xx)	1974-11-05
BR7306999D0 (pt)	1974-06-27
ES418627A1 (es)	1976-02-16
TR18108A (tr)	1976-09-30
US3904624A (en)	1975-09-09
FR2198697B1 (xx)	1975-09-12
IT1047946B (it)	1980-10-20
CH575430A5 (xx)	1976-05-14
OA04553A (fr)	1980-04-30
SU733504A3 (ru)	1980-05-05

Publication	Publication Date	Title
IL43034A (en)	1976-05-31	Phosphorus-containing esters of condensed ring pyrimidine derivatives,process for their preparation and compositions containing them
US3309266A (en)	1967-03-14	Insecticidal compositions containing oalkyl-s-alkyl phosphoroamidothioates and methods for killing insects therewith
US2908605A (en)	1959-10-13	New organic phosphorus compounds and process for their manufacture
US3857838A (en)	1974-12-31	Organophosphate ester derivatives of heterocyclic compounds and process
HU186981B (en)	1985-10-28	Pesticide compositions containing alkyl-thio-phosphate with alpha-branching as active substance and process for preparing the active substances thereof
KR870000643B1 (ko)	1987-04-03	옥심포스페이트 화합물의 제조방법
US3248412A (en)	1966-04-26	Thiophosphonic acid esters
US3733376A (en)	1973-05-15	Phosphoric acid esters
US3562288A (en)	1971-02-09	Heterocyclic phosphoric acid esters,their manufacture and use as pesticides
US4000267A (en)	1976-12-28	Insecticidal and acaricidal compositions employing pyrido[1,2a]pyrimidinone thiophosphates
US4020076A (en)	1977-04-26	Novel phosphoryloxy-thiazoles
US3301749A (en)	1967-01-31	Pesticidal omicron, omicron-dimethyl-omicron-(2-[or 3-] methoxy-4-cyanophenyl) phosphorothioate
US3265773A (en)	1966-08-09	Alkoxymethylenamides of omicron, omicron-dialkylthio-or omicron, omicron-dialkyl-dithiophosphorylacetic acids
US3801577A (en)	1974-04-02	Phosphoric and thiophosphoric acid derivatives of quinoxaline
US4128562A (en)	1978-12-05	Novel 3-(phosphoryloxy) and (phosphonyloxy)-thiophenes
US3886274A (en)	1975-05-27	Control of animal pests with 3H-oxazol-{8 4,5-6{9 pyridine-2-one esters of 3-(-o-)or (-s-)-0,0{40 di(lower alkyl) phosphates and thiophosphates
US3808218A (en)	1974-04-30	3h-oxazolo(4,5-b)pyridine-2-one,esters with 3-(-o-)or(-s-)-o,o'-diloweralkyl phosphates or thiophosphates
HU176606B (en)	1981-03-28	Insecticide,acaricide and nematocide preparations containing new thiophene-phosphor derivatives and process for preparing the nctive substance thereof
US3929809A (en)	1975-12-30	Oxazolo-{8 4,5-b{9 -pyridine-2-ones and -2-thiones as intermediates
EP0224217B1 (de)	1989-06-21	Phosphorsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schädlingen
US3445484A (en)	1969-05-20	Organic phosphorus compounds
US2943015A (en)	1960-06-28	Omicron:omicron'-diethyl s-(beta-dimethyl amino-beta-methyl)-propyl phosphorothiolates and pesticidal compositions containing same
US3390209A (en)	1968-06-25	Sulfur containing diphenylene diphosphates
US3284546A (en)	1966-11-08	Thiophosphoric esters
US3830884A (en)	1974-08-20	Dialkylsulfoximinocarbonylmethyl thiophosphates and process for preparation thereof