IL33697A - 3-(tetrahydropyran-2-yl)1,2,3,4,6,7-hexahydro-5h-cyclopentapyrimidine-2,4-dione and process for preparing same - Google Patents
3-(tetrahydropyran-2-yl)1,2,3,4,6,7-hexahydro-5h-cyclopentapyrimidine-2,4-dione and process for preparing sameInfo
- Publication number
- IL33697A IL33697A IL33697A IL3369770A IL33697A IL 33697 A IL33697 A IL 33697A IL 33697 A IL33697 A IL 33697A IL 3369770 A IL3369770 A IL 3369770A IL 33697 A IL33697 A IL 33697A
- Authority
- IL
- Israel
- Prior art keywords
- chosen
- urea
- group
- control
- hexahydro
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- JTZXTHKQUJKKEN-UHFFFAOYSA-N 3-(oxan-2-yl)-1,5,6,7-tetrahydrocyclopenta[d]pyrimidine-2,4-dione Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCO1 JTZXTHKQUJKKEN-UHFFFAOYSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 230000000361 pesticidal effect Effects 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 235000013877 carbamide Nutrition 0.000 claims 4
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 238000005342 ion exchange Methods 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 230000002363 herbicidal effect Effects 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 240000001592 Amaranthus caudatus Species 0.000 description 3
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241000219793 Trifolium Species 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- FANBESOFXBDQSH-UHFFFAOYSA-N Ethyladipic acid Chemical compound CCC(C(O)=O)CCCC(O)=O FANBESOFXBDQSH-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
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- -1 ammonium salt salt Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- JHZPNBKZPAWCJD-UHFFFAOYSA-N ethyl 2-oxocyclopentane-1-carboxylate Chemical compound CCOC(=O)C1CCCC1=O JHZPNBKZPAWCJD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- URXNVXOMQQCBHS-UHFFFAOYSA-N naphthalene;sodium Chemical compound [Na].C1=CC=CC2=CC=CC=C21 URXNVXOMQQCBHS-UHFFFAOYSA-N 0.000 description 1
- OGDOBXMNVNGETJ-UHFFFAOYSA-N oxan-2-ylurea Chemical compound NC(=O)NC1CCCCO1 OGDOBXMNVNGETJ-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 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
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/14—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR6901011A FR2029250A5 (de) | 1969-01-21 | 1969-01-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL33697A0 IL33697A0 (en) | 1970-03-22 |
| IL33697A true IL33697A (en) | 1973-04-30 |
Family
ID=9028038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL33697A IL33697A (en) | 1969-01-21 | 1970-01-13 | 3-(tetrahydropyran-2-yl)1,2,3,4,6,7-hexahydro-5h-cyclopentapyrimidine-2,4-dione and process for preparing same |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US3658819A (de) |
| AT (2) | AT297702B (de) |
| BE (1) | BE744602A (de) |
| CA (1) | CA966129A (de) |
| CH (1) | CH522674A (de) |
| DE (1) | DE2002586A1 (de) |
| ES (1) | ES375689A1 (de) |
| FR (1) | FR2029250A5 (de) |
| GB (2) | GB1255892A (de) |
| IL (1) | IL33697A (de) |
| LU (1) | LU60208A1 (de) |
| NL (1) | NL7000628A (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4337261A (en) * | 1980-07-28 | 1982-06-29 | Hoechst-Roussel Pharmaceuticals Inc. | (1,2-Benzisoxazol)phenoxyacetic acids as diuretics |
| FR2590767A1 (fr) * | 1985-12-02 | 1987-06-05 | Soyez Jean Louis | Nouvelle utilisation d'un uracile substitue et de ses associations comme herbicide selectif sur culture de mais |
| MY152292A (en) * | 2008-05-13 | 2014-09-15 | Boehringer Ingelheim Int | Synthesis of dihydrothieno[3,2-d]pyrimidine diols and similar pyrimidine diols |
-
1969
- 1969-01-21 FR FR6901011A patent/FR2029250A5/fr not_active Expired
-
1970
- 1970-01-13 IL IL33697A patent/IL33697A/en unknown
- 1970-01-16 US US3499A patent/US3658819A/en not_active Expired - Lifetime
- 1970-01-16 NL NL7000628A patent/NL7000628A/xx not_active Application Discontinuation
- 1970-01-16 CH CH63570A patent/CH522674A/fr not_active IP Right Cessation
- 1970-01-19 BE BE744602D patent/BE744602A/xx unknown
- 1970-01-20 CA CA072,659A patent/CA966129A/en not_active Expired
- 1970-01-20 LU LU60208D patent/LU60208A1/xx unknown
- 1970-01-20 ES ES375689A patent/ES375689A1/es not_active Expired
- 1970-01-21 DE DE19702002586 patent/DE2002586A1/de active Pending
- 1970-01-21 AT AT56370A patent/AT297702B/de not_active IP Right Cessation
- 1970-01-21 GB GB8998/71A patent/GB1255892A/en not_active Expired
- 1970-01-21 AT AT399771A patent/AT307142B/de not_active IP Right Cessation
- 1970-01-21 GB GB3021/70A patent/GB1255891A/en not_active Expired
-
1971
- 1971-10-08 US US00187914A patent/US3785800A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES375689A1 (es) | 1972-05-16 |
| GB1255891A (en) | 1971-12-01 |
| FR2029250A5 (de) | 1970-10-16 |
| IL33697A0 (en) | 1970-03-22 |
| CA966129A (en) | 1975-04-15 |
| US3785800A (en) | 1974-01-15 |
| NL7000628A (de) | 1970-07-23 |
| GB1255892A (en) | 1971-12-01 |
| LU60208A1 (de) | 1970-03-20 |
| AT297702B (de) | 1972-04-10 |
| BE744602A (fr) | 1970-07-20 |
| AT307142B (de) | 1973-05-10 |
| US3658819A (en) | 1972-04-25 |
| DE2002586A1 (de) | 1970-08-27 |
| CH522674A (fr) | 1972-06-30 |
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