CS209945B2 - Herbicide means and method of making the active substance - Google Patents
Herbicide means and method of making the active substance Download PDFInfo
- Publication number
- CS209945B2 CS209945B2 CS80369A CS36980A CS209945B2 CS 209945 B2 CS209945 B2 CS 209945B2 CS 80369 A CS80369 A CS 80369A CS 36980 A CS36980 A CS 36980A CS 209945 B2 CS209945 B2 CS 209945B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- chlorine
- formula
- hydrogen
- water
- dichloro
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 8
- 239000013543 active substance Substances 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000004009 herbicide Substances 0.000 title description 3
- 239000000460 chlorine Substances 0.000 claims abstract description 63
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 39
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
- 239000001257 hydrogen Substances 0.000 claims abstract description 35
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 22
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 4
- 238000000034 method Methods 0.000 claims description 122
- 238000006243 chemical reaction Methods 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 239000004480 active ingredient Substances 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- YQHHCMVUMULAPZ-UHFFFAOYSA-N C[CH2+] Chemical compound C[CH2+] YQHHCMVUMULAPZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- QAJJXHRQPLATMK-UHFFFAOYSA-N 4,5-dichloro-1h-imidazole Chemical class ClC=1N=CNC=1Cl QAJJXHRQPLATMK-UHFFFAOYSA-N 0.000 abstract description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 239000005864 Sulphur Substances 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 77
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 57
- 150000001875 compounds Chemical class 0.000 description 56
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 50
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 47
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 35
- 241000196324 Embryophyta Species 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- -1 aliphatic nitrile Chemical class 0.000 description 32
- 239000003795 chemical substances by application Substances 0.000 description 32
- 239000007795 chemical reaction product Substances 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 26
- 239000007858 starting material Substances 0.000 description 25
- 238000001816 cooling Methods 0.000 description 21
- 239000003085 diluting agent Substances 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 238000007796 conventional method Methods 0.000 description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000002329 infrared spectrum Methods 0.000 description 12
- 235000009518 sodium iodide Nutrition 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 11
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- 239000000047 product Substances 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 9
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- 238000010992 reflux Methods 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 229910021538 borax Inorganic materials 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
- 239000011630 iodine Substances 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 235000010339 sodium tetraborate Nutrition 0.000 description 7
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000003638 chemical reducing agent Substances 0.000 description 6
- 238000003776 cleavage reaction Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 230000007017 scission Effects 0.000 description 6
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- YZXNUSFREIVOLU-UHFFFAOYSA-N 1-(4,5-dichloro-1h-imidazol-2-yl)ethanone Chemical compound CC(=O)C1=NC(Cl)=C(Cl)N1 YZXNUSFREIVOLU-UHFFFAOYSA-N 0.000 description 5
- OHWPJJSEYPMDRU-UHFFFAOYSA-N 2,4,5-trichloro-2-(1,1-dichloroethyl)imidazole Chemical compound CC(Cl)(Cl)C1(Cl)N=C(Cl)C(Cl)=N1 OHWPJJSEYPMDRU-UHFFFAOYSA-N 0.000 description 5
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 5
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- 238000005984 hydrogenation reaction Methods 0.000 description 5
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- SOSFZRABIFHKBM-UHFFFAOYSA-N 4,5-dichloro-2-(1,1,2,2,2-pentachloroethyl)-1h-imidazole Chemical compound ClC=1N=C(C(Cl)(Cl)C(Cl)(Cl)Cl)NC=1Cl SOSFZRABIFHKBM-UHFFFAOYSA-N 0.000 description 4
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- 235000011684 Sorghum saccharatum Nutrition 0.000 description 4
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- 229910000510 noble metal Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- MZQCFPABNHFYAT-UHFFFAOYSA-M sodium;propan-2-one;iodide Chemical compound [Na+].[I-].CC(C)=O MZQCFPABNHFYAT-UHFFFAOYSA-M 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- ZBOGUDPFEVIZIQ-UHFFFAOYSA-N toluene;dihydrochloride Chemical compound Cl.Cl.CC1=CC=CC=C1 ZBOGUDPFEVIZIQ-UHFFFAOYSA-N 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/68—Halogen atoms
-
- 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
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792901862 DE2901862A1 (de) | 1979-01-18 | 1979-01-18 | 4,5-dichlorimidazol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS209945B2 true CS209945B2 (en) | 1981-12-31 |
Family
ID=6060864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS80369A CS209945B2 (en) | 1979-01-18 | 1980-01-18 | Herbicide means and method of making the active substance |
Country Status (15)
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1567084A1 (de) * | 1963-07-01 | 1970-10-15 | Shell Int Research | Mittel zur Bekaempfung unerwuenschten Pflanzenwuchses |
| DE1926206A1 (de) * | 1969-05-22 | 1970-11-26 | Bayer Ag | Verfahren zur Herstellung von Acylimidazolen |
| DE2610527A1 (de) * | 1976-03-12 | 1977-09-29 | Bayer Ag | 4,5-dichlorimidazol-2-carbonsaeurederivate, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide, fungizide und wachstumsregulatoren |
-
1979
- 1979-01-18 DE DE19792901862 patent/DE2901862A1/de not_active Withdrawn
-
1980
- 1980-01-10 EP EP80100105A patent/EP0013905B1/de not_active Expired
- 1980-01-10 AT AT80100105T patent/ATE966T1/de not_active IP Right Cessation
- 1980-01-10 PT PT70683A patent/PT70683A/pt unknown
- 1980-01-10 DE DE8080100105T patent/DE3060344D1/de not_active Expired
- 1980-01-15 IL IL59129A patent/IL59129A0/xx unknown
- 1980-01-16 DD DD80218486A patent/DD148582A5/de unknown
- 1980-01-17 BR BR8000295A patent/BR8000295A/pt unknown
- 1980-01-17 ZA ZA00800292A patent/ZA80292B/xx unknown
- 1980-01-17 PL PL22145380A patent/PL221453A1/xx unknown
- 1980-01-17 DK DK21080A patent/DK21080A/da unknown
- 1980-01-17 CA CA000343849A patent/CA1135703A/en not_active Expired
- 1980-01-17 ES ES487791A patent/ES487791A1/es not_active Expired
- 1980-01-17 AU AU54677/80A patent/AU5467780A/en not_active Abandoned
- 1980-01-18 CS CS80369A patent/CS209945B2/cs unknown
- 1980-01-18 JP JP372580A patent/JPS55100370A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0013905B1 (de) | 1982-05-05 |
| IL59129A0 (en) | 1980-05-30 |
| PL221453A1 (enrdf_load_stackoverflow) | 1980-12-15 |
| JPS55100370A (en) | 1980-07-31 |
| DD148582A5 (de) | 1981-06-03 |
| ATE966T1 (de) | 1982-05-15 |
| EP0013905A1 (de) | 1980-08-06 |
| AU5467780A (en) | 1980-07-24 |
| ZA80292B (en) | 1981-01-28 |
| DK21080A (da) | 1980-07-19 |
| DE2901862A1 (de) | 1980-07-31 |
| ES487791A1 (es) | 1980-06-16 |
| CA1135703A (en) | 1982-11-16 |
| BR8000295A (pt) | 1980-10-21 |
| DE3060344D1 (en) | 1982-06-24 |
| PT70683A (en) | 1980-02-01 |
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