HU199431B - Process for producing carbendazim salts, and fungicide comprising such carbendazim salt as active ingredient - Google Patents
Process for producing carbendazim salts, and fungicide comprising such carbendazim salt as active ingredient Download PDFInfo
- Publication number
- HU199431B HU199431B HU85411A HU41185A HU199431B HU 199431 B HU199431 B HU 199431B HU 85411 A HU85411 A HU 85411A HU 41185 A HU41185 A HU 41185A HU 199431 B HU199431 B HU 199431B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- acid
- salts
- carbendazim
- aminobenzimidazolylmethylcarbamate
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 4
- 239000004480 active ingredient Substances 0.000 title claims description 3
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical class C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 title 2
- 239000000417 fungicide Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000000440 bentonite Substances 0.000 claims description 2
- 229910000278 bentonite Inorganic materials 0.000 claims description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical group O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000002480 mineral oil Substances 0.000 claims description 2
- 235000010446 mineral oil Nutrition 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000005909 Kieselgur Substances 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 229910052902 vermiculite Inorganic materials 0.000 claims 1
- 239000010455 vermiculite Substances 0.000 claims 1
- 235000019354 vermiculite Nutrition 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- -1 dusts Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 8
- 239000007921 spray Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- JLSKLHBINCXCMI-UHFFFAOYSA-N (2-amino-1H-benzimidazol-4-yl)methylcarbamic acid Chemical compound C1=CC(=C2C(=C1)NC(=N2)N)CNC(=O)O JLSKLHBINCXCMI-UHFFFAOYSA-N 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- REFGVLUGGLUATM-UHFFFAOYSA-N (2-amino-4-methyl-1H-benzimidazol-5-yl)methylcarbamic acid Chemical class CC1=C(C=CC2=C1N=C(N2)N)CNC(=O)O REFGVLUGGLUATM-UHFFFAOYSA-N 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical class C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 240000004731 Acer pseudoplatanus Species 0.000 description 2
- 235000002754 Acer pseudoplatanus Nutrition 0.000 description 2
- 241000221785 Erysiphales Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 235000006485 Platanus occidentalis Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 0 CC*N(*C(C)=*C(CC1)C(*)CCC1(*(C)C)O)O Chemical compound CC*N(*C(C)=*C(CC1)C(*)CCC1(*(C)C)O)O 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 239000006013 carbendazim Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000007882 cirrhosis Effects 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- CRVVHBFLWWQMPT-UHFFFAOYSA-N naphthalene-1-sulfonic acid;sodium Chemical compound [Na].C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 CRVVHBFLWWQMPT-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003090 pesticide formulation Substances 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 230000008659 phytopathology Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000008653 root damage Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU85411A HU199431B (en) | 1985-02-04 | 1985-02-04 | Process for producing carbendazim salts, and fungicide comprising such carbendazim salt as active ingredient |
| DE19863602881 DE3602881A1 (de) | 1985-02-04 | 1986-01-31 | Neue fungizid wirkende salze, verfahren zu deren herstellung und diese verbindungen enthaltende agrochemische praeparate |
| CN198686100998A CN86100998A (zh) | 1985-02-04 | 1986-02-03 | 新的杀菌剂 |
| IT19279/86A IT1204776B (it) | 1985-02-04 | 1986-02-03 | Fungicidi a base di carbendazim |
| ES551978A ES8705866A1 (es) | 1985-02-04 | 1986-02-04 | Procedimiento de preparar sales fungicidas |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU85411A HU199431B (en) | 1985-02-04 | 1985-02-04 | Process for producing carbendazim salts, and fungicide comprising such carbendazim salt as active ingredient |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT39729A HUT39729A (en) | 1986-10-29 |
| HU199431B true HU199431B (en) | 1990-02-28 |
Family
ID=10949495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU85411A HU199431B (en) | 1985-02-04 | 1985-02-04 | Process for producing carbendazim salts, and fungicide comprising such carbendazim salt as active ingredient |
Country Status (5)
| Country | Link |
|---|---|
| CN (1) | CN86100998A (es) |
| DE (1) | DE3602881A1 (es) |
| ES (1) | ES8705866A1 (es) |
| HU (1) | HU199431B (es) |
| IT (1) | IT1204776B (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006519852A (ja) * | 2003-03-12 | 2006-08-31 | アリゾナ ボード オブ リージェンツ オン ビハーフ オブ ザ ユニバーシティー オブ アリゾナ | 弱塩基の塩 |
| CN104945330B (zh) * | 2015-07-14 | 2017-06-16 | 江苏泰仓农化有限公司 | 一种苯菌灵生产设备 |
| CN108383797B (zh) * | 2018-03-09 | 2020-07-21 | 浙江农林大学 | 一种防腐化合物及其制备方法与应用 |
-
1985
- 1985-02-04 HU HU85411A patent/HU199431B/hu not_active IP Right Cessation
-
1986
- 1986-01-31 DE DE19863602881 patent/DE3602881A1/de not_active Withdrawn
- 1986-02-03 CN CN198686100998A patent/CN86100998A/zh active Pending
- 1986-02-03 IT IT19279/86A patent/IT1204776B/it active
- 1986-02-04 ES ES551978A patent/ES8705866A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT8619279A0 (it) | 1986-02-03 |
| ES8705866A1 (es) | 1987-06-01 |
| CN86100998A (zh) | 1986-11-12 |
| ES551978A0 (es) | 1987-06-01 |
| DE3602881A1 (de) | 1986-08-07 |
| IT1204776B (it) | 1989-03-10 |
| HUT39729A (en) | 1986-10-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0113091B1 (de) | Mikrobizide Mittel auf Chinoloncarbonsäure-Basis | |
| PL156233B1 (en) | Agent for fighting against harmflul insects or microorganisms or preventing an injurious attack by them | |
| EP0071568B1 (de) | Mandelsäure-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Mikroorganismen | |
| KR20070050449A (ko) | 메소트리온 다형체의 제조방법 | |
| EP0304282A1 (en) | Process for preparing sulfonylurea salts | |
| JPS5823671A (ja) | イミダゾリル−ｏ，ｎ−アセタ−ルおよびその塩の製法 | |
| US3773960A (en) | Acaracidal compositions and methods comprising aliphatically substituted thiosulfinyl-and sulfonyl-alkyl-2,4,5-trihalogeno imidazoles | |
| JPS5912669B2 (ja) | １−プロピル−１，２，４−トリアゾリル誘導体およびそれらの塩の製造法 | |
| EP0193875A2 (de) | Fungizide Mittel auf der Basis von 3-(Hetero)-Arylpropylaminen sowie neue (Hetero)-Arylpropylamine und Verfahren zu ihrer Herstellung | |
| WO2012084857A2 (de) | Verfahren zur herstellung von 2-(triazinylcarbonyl)sulfonaniliden | |
| JPH049788B2 (es) | ||
| EP1384714A1 (en) | Pyrazolecarboxamide derivative, intermediate therefor, and pest control agent containing the same as active ingredient | |
| EP0163606B1 (de) | Mikrobizide 1-Fluor-1-azolyl-2,2-diarylethanderivate | |
| HU199431B (en) | Process for producing carbendazim salts, and fungicide comprising such carbendazim salt as active ingredient | |
| DE2527677A1 (de) | Verfahren zur herstellung von 2,4- dioxo-1,2,3,4-tetrahydro-s-triazino- eckige klammer auf 1,2-a eckige klammer zu -benzimidazolen | |
| KR900002708B1 (ko) | 트리스(β,β-디메틸펜에틸)주석 화합물의 제조방법 | |
| DE2744385C2 (de) | Biocide Mittel und Verfahren zur Herstellung der darin enthaltenen Wirkstoffe | |
| US4579853A (en) | 2-Cyano-imidazopyridine derivatives and their use as fungicides | |
| DE69111674T2 (de) | Fungizide Verbindungen und Zusammensetzungen, die Tris(aryl)-phosphonium Salze enthalten. | |
| DE3601688A1 (de) | Naphthyridin-derivate, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider wirkung | |
| DE4142128C2 (de) | Verfahren zur Herstellung von Verbindungen mit einer oder mehreren Thiocyanatomethylthio-Gruppierungen | |
| KR790001342B1 (ko) | 트리아졸릴-0, n-아세탈류의 제법 | |
| US2980580A (en) | Cycloheximide acetate horticultural fungicidal composition and method of use | |
| FR2607811A1 (fr) | Derives de sulfonyl benzimidazole, leur preparation ainsi que leur utilisation a titre de fongicides | |
| US3247217A (en) | Certain benzimidazole derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |