DE2528604A1 - Pyrazoliniumsalze und verfahren zu ihrer herstellung - Google Patents
Pyrazoliniumsalze und verfahren zu ihrer herstellungInfo
- Publication number
- DE2528604A1 DE2528604A1 DE19752528604 DE2528604A DE2528604A1 DE 2528604 A1 DE2528604 A1 DE 2528604A1 DE 19752528604 DE19752528604 DE 19752528604 DE 2528604 A DE2528604 A DE 2528604A DE 2528604 A1 DE2528604 A1 DE 2528604A1
- Authority
- DE
- Germany
- Prior art keywords
- pyrazolinium
- hydrogen
- dimethyl
- phenyl
- methyl
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 41
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000003219 pyrazolines Chemical class 0.000 title 1
- 241000196324 Embryophyta Species 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- -1 methoxy, methylthio, methylsulfinyl Chemical group 0.000 claims description 25
- KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical class C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 150000001450 anions Chemical class 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 240000007594 Oryza sativa Species 0.000 claims description 14
- 235000007164 Oryza sativa Nutrition 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 235000009566 rice Nutrition 0.000 claims description 12
- 240000005979 Hordeum vulgare Species 0.000 claims description 11
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- 241000209140 Triticum Species 0.000 claims description 11
- 235000021307 Triticum Nutrition 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 235000007320 Avena fatua Nutrition 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 8
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- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000012279 sodium borohydride Substances 0.000 claims description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 244000045561 useful plants Species 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 230000003032 phytopathogenic effect Effects 0.000 claims 6
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- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 1
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- 150000003254 radicals Chemical class 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
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- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
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- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 3
- 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 2
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- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 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 1
- 230000001795 light effect Effects 0.000 description 1
- 230000036244 malformation Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical class COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US484515A US3925408A (en) | 1974-07-01 | 1974-07-01 | Pyrazolinium compounds as herbicides |
| US05/540,736 US3947583A (en) | 1975-01-13 | 1975-01-13 | Method for controlling fungi utilizing pyrazolinium compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2528604A1 true DE2528604A1 (de) | 1976-01-22 |
Family
ID=27048024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752528604 Pending DE2528604A1 (de) | 1974-07-01 | 1975-06-26 | Pyrazoliniumsalze und verfahren zu ihrer herstellung |
Country Status (12)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1151890A (en) * | 1980-02-19 | 1983-08-16 | American Cyanamid Company | Method for dwarfing the stem of sunflowers and cotton |
-
1975
- 1975-06-12 GB GB2522775A patent/GB1468136A/en not_active Expired
- 1975-06-12 IN IN1160/CAL/1975A patent/IN141872B/en unknown
- 1975-06-16 IL IL47484A patent/IL47484A0/xx unknown
- 1975-06-23 AR AR259304A patent/AR215118A1/es active
- 1975-06-26 DE DE19752528604 patent/DE2528604A1/de active Pending
- 1975-06-27 DK DK294075AA patent/DK137822B/da unknown
- 1975-06-30 SE SE7507477A patent/SE7507477L/xx unknown
- 1975-07-01 JP JP50081390A patent/JPS5134157A/ja active Pending
- 1975-07-01 NL NL7507819A patent/NL7507819A/xx not_active Application Discontinuation
- 1975-07-01 ES ES439028A patent/ES439028A1/es not_active Expired
- 1975-07-01 FR FR7520665A patent/FR2277086A1/fr active Granted
- 1975-07-01 DD DD186998A patent/DD121108A5/xx unknown
-
1977
- 1977-01-03 ES ES454759A patent/ES454759A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IN141872B (enrdf_load_stackoverflow) | 1977-04-30 |
| JPS5134157A (en) | 1976-03-23 |
| DK294075A (enrdf_load_stackoverflow) | 1976-01-02 |
| DK137822C (enrdf_load_stackoverflow) | 1978-10-23 |
| FR2277086B1 (enrdf_load_stackoverflow) | 1978-09-22 |
| IL47484A0 (en) | 1975-08-31 |
| ES439028A1 (es) | 1977-06-16 |
| AU8207875A (en) | 1976-12-16 |
| SE7507477L (sv) | 1976-01-02 |
| ES454759A1 (es) | 1978-01-01 |
| FR2277086A1 (fr) | 1976-01-30 |
| GB1468136A (en) | 1977-03-23 |
| DD121108A5 (enrdf_load_stackoverflow) | 1976-07-12 |
| NL7507819A (nl) | 1976-01-05 |
| AR215118A1 (es) | 1979-09-14 |
| DK137822B (da) | 1978-05-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |