DE889297C - Verfahren zur Herstellung von substituierten Tetrahydropyrimidin-Derivaten - Google Patents
Verfahren zur Herstellung von substituierten Tetrahydropyrimidin-DerivatenInfo
- Publication number
- DE889297C DE889297C DEN3973A DEN0003973A DE889297C DE 889297 C DE889297 C DE 889297C DE N3973 A DEN3973 A DE N3973A DE N0003973 A DEN0003973 A DE N0003973A DE 889297 C DE889297 C DE 889297C
- Authority
- DE
- Germany
- Prior art keywords
- tetrahydropyrimidine
- preparation
- trimethyl
- tert
- acid
- 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 title claims description 8
- 150000005326 tetrahydropyrimidines Chemical class 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- 229940058307 antinematodal tetrahydropyrimidine derivative Drugs 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- -1 B. with z Chemical class 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001559 benzoic acids Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- YZTDHNFXEQKPGK-UHFFFAOYSA-N 1,6-diaminohexane-2,5-dione Chemical compound C(CCC(=O)CN)(=O)CN YZTDHNFXEQKPGK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 230000000855 fungicidal effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- VBXZSFNZVNDOPB-UHFFFAOYSA-N 1,4,5,6-tetrahydropyrimidine Chemical compound C1CNC=NC1 VBXZSFNZVNDOPB-UHFFFAOYSA-N 0.000 description 2
- PCXAQLMRLMZKRL-UHFFFAOYSA-N 2-methylpentane-2,4-diamine Chemical compound CC(N)CC(C)(C)N PCXAQLMRLMZKRL-UHFFFAOYSA-N 0.000 description 2
- SYAXQMHGHKBJHC-UHFFFAOYSA-N C1(=CC=C(C=C1)C1=NC(CC(N1)(C)C)C)C Chemical compound C1(=CC=C(C=C1)C1=NC(CC(N1)(C)C)C)C SYAXQMHGHKBJHC-UHFFFAOYSA-N 0.000 description 2
- 241000227653 Lycopersicon Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 description 1
- 150000005327 1,4,5,6-tetrahydropyrimidines Chemical class 0.000 description 1
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
- XPOBCKRZDTXQBO-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-1,4,5,6-tetrahydropyrimidine Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C1=NCCCN1 XPOBCKRZDTXQBO-UHFFFAOYSA-N 0.000 description 1
- JVXRNEHSONZKJO-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4,6,6-trimethyl-4,5-dihydro-1h-pyrimidine Chemical compound CC1CC(C)(C)NC(C=2C=CC(=CC=2)C(C)(C)C)=N1 JVXRNEHSONZKJO-UHFFFAOYSA-N 0.000 description 1
- NCTSLPBQVXUAHR-UHFFFAOYSA-N 3,5-ditert-butylbenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(C)(C)C)=C1 NCTSLPBQVXUAHR-UHFFFAOYSA-N 0.000 description 1
- ZQLDNJKHLQOJGE-UHFFFAOYSA-N 4-octylbenzoic acid Chemical compound CCCCCCCCC1=CC=C(C(O)=O)C=C1 ZQLDNJKHLQOJGE-UHFFFAOYSA-N 0.000 description 1
- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- QYORQJIYUBOJMY-UHFFFAOYSA-N C(CCCCCCC)C1=CC=C(C=C1)C1=NC(CC(N1)(C)C)C Chemical compound C(CCCCCCC)C1=CC=C(C=C1)C1=NC(CC(N1)(C)C)C QYORQJIYUBOJMY-UHFFFAOYSA-N 0.000 description 1
- LEJMGJONKOTTTC-UHFFFAOYSA-N C1(=C(C=CC=C1)C1=NC(CC(N1)(C)C)C)C Chemical compound C1(=C(C=CC=C1)C1=NC(CC(N1)(C)C)C)C LEJMGJONKOTTTC-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- LPNBBFKOUUSUDB-UHFFFAOYSA-M p-toluate Chemical compound CC1=CC=C(C([O-])=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-M 0.000 description 1
- 125000005489 p-toluenesulfonic acid group Chemical class 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- GNCGTEQGBYYYBX-UHFFFAOYSA-M sodium;4-methylbenzoate Chemical compound [Na+].CC1=CC=C(C([O-])=O)C=C1 GNCGTEQGBYYYBX-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 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
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US298428XA | 1950-05-31 | 1950-05-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE889297C true DE889297C (de) | 1953-09-10 |
Family
ID=26705401
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEN3973A Expired DE889297C (de) | 1950-05-31 | 1951-05-31 | Verfahren zur Herstellung von substituierten Tetrahydropyrimidin-Derivaten |
| DEN3974A Expired DE880523C (de) | 1950-05-31 | 1951-06-01 | Verfahren zur Bekaempfung von Pilzen |
| DEN7596A Expired DE940740C (de) | 1950-05-31 | 1953-08-15 | Verfahren zur Bekaempfung von Pilzen |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEN3974A Expired DE880523C (de) | 1950-05-31 | 1951-06-01 | Verfahren zur Bekaempfung von Pilzen |
| DEN7596A Expired DE940740C (de) | 1950-05-31 | 1953-08-15 | Verfahren zur Bekaempfung von Pilzen |
Country Status (7)
| Country | Link |
|---|---|
| BE (2) | BE503641A (en:Method) |
| CH (2) | CH298428A (en:Method) |
| DE (3) | DE889297C (en:Method) |
| ES (1) | ES198115A1 (en:Method) |
| FR (2) | FR1043036A (en:Method) |
| GB (2) | GB685103A (en:Method) |
| NL (1) | NL78483C (en:Method) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3169848A (en) * | 1955-12-21 | 1965-02-16 | Geigy Ag J R | Composition and method for inhibiting the growth of plants |
| GB869977A (en) * | 1957-12-26 | 1961-06-07 | Pfizer & Co C | Diazacycloalkenes and the preparation thereof |
| US3227612A (en) * | 1962-07-23 | 1966-01-04 | Pfister Chemical Works Inc | Process of combatting fungal infestations with ring chlorinated pyrimidines |
| US5162526A (en) * | 1976-09-24 | 1992-11-10 | Exxon Chemical Patents Inc. | Macrocyclic polyamine and polycyclic polyamine multifunctional lubricating oil |
| US4539140A (en) * | 1980-10-27 | 1985-09-03 | Petrolite Corporation | Mixtures of non-halogen salts of nitrogen heterocyclics and nitrogen-sulfur heterocyclics |
| US4525296A (en) * | 1980-10-27 | 1985-06-25 | Petrolite Corporation | Halide free corrosion inhibitors |
| US4559163A (en) * | 1980-10-27 | 1985-12-17 | Petrolite Corporation | Halide free octahydrophenanthridine corrosion inhibitors |
| US4514320A (en) * | 1980-10-27 | 1985-04-30 | Petrolite Corporation | Halide free corrosion inhibitors |
| GB9016800D0 (en) * | 1990-07-31 | 1990-09-12 | Shell Int Research | Tetrahydropyrimidine derivatives |
-
0
- BE BE522124D patent/BE522124A/xx unknown
- BE BE503641D patent/BE503641A/xx unknown
-
1931
- 1931-05-31 NL NL161635A patent/NL78483C/xx active
-
1951
- 1951-05-29 FR FR1043036D patent/FR1043036A/fr not_active Expired
- 1951-05-30 CH CH298428D patent/CH298428A/de unknown
- 1951-05-31 DE DEN3973A patent/DE889297C/de not_active Expired
- 1951-05-31 GB GB12921/51A patent/GB685103A/en not_active Expired
- 1951-05-31 ES ES0198115A patent/ES198115A1/es not_active Expired
- 1951-06-01 DE DEN3974A patent/DE880523C/de not_active Expired
-
1953
- 1953-08-13 FR FR64543D patent/FR64543E/fr not_active Expired
- 1953-08-14 GB GB22412/53A patent/GB740936A/en not_active Expired
- 1953-08-15 DE DEN7596A patent/DE940740C/de not_active Expired
- 1953-08-15 CH CH318353D patent/CH318353A/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE503641A (en:Method) | |
| DE880523C (de) | 1953-06-22 |
| DE940740C (de) | 1956-03-22 |
| CH318353A (de) | 1956-12-31 |
| GB740936A (en) | 1955-11-23 |
| ES198115A1 (es) | 1951-07-01 |
| FR1043036A (fr) | 1953-11-05 |
| NL78483C (en:Method) | 1955-02-15 |
| GB685103A (en) | 1952-12-31 |
| FR64543E (fr) | 1955-11-14 |
| CH298428A (de) | 1954-05-15 |
| BE522124A (en:Method) |
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