DE2521384C2 - Flüssigformulierungen mit fungitoxischer und akarizider Wirkung - Google Patents
Flüssigformulierungen mit fungitoxischer und akarizider WirkungInfo
- Publication number
- DE2521384C2 DE2521384C2 DE2521384A DE2521384A DE2521384C2 DE 2521384 C2 DE2521384 C2 DE 2521384C2 DE 2521384 A DE2521384 A DE 2521384A DE 2521384 A DE2521384 A DE 2521384A DE 2521384 C2 DE2521384 C2 DE 2521384C2
- Authority
- DE
- Germany
- Prior art keywords
- ion
- liquid formulations
- emulsifier
- dbs
- salt
- 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
- 239000012669 liquid formulation Substances 0.000 title claims description 13
- 230000000895 acaricidal effect Effects 0.000 title description 2
- 230000002464 fungitoxic effect Effects 0.000 title description 2
- 231100000162 fungitoxic Toxicity 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 20
- 239000003995 emulsifying agent Substances 0.000 claims description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 16
- 238000009472 formulation Methods 0.000 claims description 14
- -1 Amine salt Chemical class 0.000 claims description 10
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 claims description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 2
- 239000012875 nonionic emulsifier Substances 0.000 claims description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
- 229940062233 di-isopropylammonium Drugs 0.000 claims 1
- DHAFIDRKDGCXLV-UHFFFAOYSA-N n,n-dimethylformamide;1-methylpyrrolidin-2-one Chemical compound CN(C)C=O.CN1CCCC1=O DHAFIDRKDGCXLV-UHFFFAOYSA-N 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- FODHIQQNHOPUKH-UHFFFAOYSA-N tetrapropylene-benzenesulfonic acid Chemical compound CC1CC11C2=C3S(=O)(=O)OC(C)CC3=C3C(C)CC3=C2C1C FODHIQQNHOPUKH-UHFFFAOYSA-N 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 72
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 21
- 239000012141 concentrate Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 12
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 4
- 101100074988 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) nmp-1 gene Proteins 0.000 description 3
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- UYLNXHPPEWDOLL-UHFFFAOYSA-N 2-dodecylbenzenesulfonate;propan-2-ylazanium Chemical compound CC(C)N.CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O UYLNXHPPEWDOLL-UHFFFAOYSA-N 0.000 description 1
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- CFSSWEQYBLCBLH-UHFFFAOYSA-N iso-hexadecyl alcohol Natural products CC(C)CCCCCCCCCCCCCO CFSSWEQYBLCBLH-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (28)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2521384A DE2521384C2 (de) | 1975-05-14 | 1975-05-14 | Flüssigformulierungen mit fungitoxischer und akarizider Wirkung |
AT301676A AT350840B (de) | 1975-05-14 | 1976-04-26 | Fluessigformulierungen mit fungitoxischer und akarizider wirkung |
CH571576A CH616053A5 (en) | 1975-05-14 | 1976-05-06 | Liquid formulation of N,N'-bis-(1-formamido-2,2,2-trichloroethyl)piperazine. |
TR18806A TR18806A (tr) | 1975-05-14 | 1976-05-07 | Fungitoksik ve akarisit etkiyi haiz olan sivi formuelasyonlar |
EG282/76D EG12223A (en) | 1975-05-14 | 1976-05-11 | N,n-bis(1-formamido-2,2,2-thichloroethyl)piperazine use as fungicide and acaricide |
GR50685A GR60312B (en) | 1975-05-14 | 1976-05-11 | Fluid compositions with fungicide and fleacide activity |
IL49564A IL49564A (en) | 1975-05-14 | 1976-05-12 | Liquid fungicidal and acaricidal compositions containing triforine |
DD192808A DD127521A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-05-14 | 1976-05-12 | |
LU74929A LU74929A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-05-14 | 1976-05-12 | |
CS763177A CS188137B2 (en) | 1975-05-14 | 1976-05-12 | Liquid preparations with the fungitoxic and acaricide effect |
IT49436/76A IT1061275B (it) | 1975-05-14 | 1976-05-12 | Composizioni liquide dotate di attivita fungitossica e acaricida |
BE167009A BE841804A (fr) | 1975-05-14 | 1976-05-13 | Formulations liquides presentant une activite fongitoxique et acaricide |
AU13908/76A AU506400B2 (en) | 1975-05-14 | 1976-05-13 | Triforine composition |
ES447867A ES447867A1 (es) | 1975-05-14 | 1976-05-13 | Procedimiento para la preparacion de formulaciones liquidas de la n, n'-bis-(1-formamido-2, 28 2-tricloroetil) piperazi-na. |
GB19822/76A GB1518562A (en) | 1975-05-14 | 1976-05-13 | Pesticidal compositions |
ZA00762872A ZA762872B (en) | 1975-05-14 | 1976-05-13 | Fluid formulations having fungitoxic and acaricidal activity |
AR263278A AR217054A1 (es) | 1975-05-14 | 1976-05-13 | Formulaciones liquidas de la n,n'-bis(1-formamido-2,2,2'-tricloroetil)piperacina,de accion fungitoxica y acaricida,utilizables como agentes protectores de las plantas |
CA252,511A CA1070239A (en) | 1975-05-14 | 1976-05-13 | Fluid formulations having fungitoxic and acaricidal activity |
JP51054803A JPS6030282B2 (ja) | 1975-05-14 | 1976-05-13 | 殺カビおよび殺ダニ調合物 |
NLAANVRAGE7605105,A NL185320C (nl) | 1975-05-14 | 1976-05-13 | Werkwijze ter bereiding van vloeibare, fungicide triforine-preparaten. |
DK215376A DK215376A (da) | 1975-05-14 | 1976-05-13 | Flydende middel med fungitoksisk og akaricid virkning |
SE7605473A SE436679B (sv) | 1975-05-14 | 1976-05-13 | Flytande beredning av n,n-bis-(1-formamido-2,2,2-trikloretyl)-piperazin med en halt av vissa angivna salter av en alkylbensensulfonsyra som emulgator |
NZ180854A NZ180854A (en) | 1975-05-14 | 1976-05-13 | Fungicidal and acaricidal compositions containing n,n'-bis-((1-formamido-2,2,2-trichloro)-ethyl)-piperazine and astabilising emulsifier |
IE1033/76A IE43688B1 (en) | 1975-05-14 | 1976-05-14 | Pesticidal compositions |
MX76237U MX4390E (es) | 1975-05-14 | 1976-05-14 | Procedimiento para preparar una composicion fungicida y acariciada |
FR7614627A FR2310701A1 (fr) | 1975-05-14 | 1976-05-14 | Formulations liquides a base de triforine presentant une activite fongitoxique et acaricide |
BR7603059A BR7603059A (pt) | 1975-05-14 | 1976-05-14 | Composicoes liquidas de n-n'-bis(1-formamido-2,2,2-tricloro-etil)piperazina |
US05/903,576 US4198410A (en) | 1975-05-14 | 1978-05-08 | Liquid fungitoxic and acaricidal compositions containing triforine |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2521384A DE2521384C2 (de) | 1975-05-14 | 1975-05-14 | Flüssigformulierungen mit fungitoxischer und akarizider Wirkung |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2521384A1 DE2521384A1 (de) | 1976-11-25 |
DE2521384C2 true DE2521384C2 (de) | 1986-11-06 |
Family
ID=5946500
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2521384A Expired DE2521384C2 (de) | 1975-05-14 | 1975-05-14 | Flüssigformulierungen mit fungitoxischer und akarizider Wirkung |
Country Status (27)
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2952239A1 (de) | 1979-12-22 | 1981-07-02 | Celamerck Gmbh & Co Kg, 6507 Ingelheim | Fungizide mischungen |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AT304164B (de) * | 1970-07-03 | 1972-12-27 | Boehringer Sohn Ingelheim | Bekämpfung von tierischen Schädlingen |
DE2306623A1 (de) * | 1973-02-10 | 1974-08-15 | Celamerck Gmbh & Co Kg | Biologisch wirksame substanzen, ihre herstellung und verwendung |
-
1975
- 1975-05-14 DE DE2521384A patent/DE2521384C2/de not_active Expired
-
1976
- 1976-04-26 AT AT301676A patent/AT350840B/de not_active IP Right Cessation
- 1976-05-06 CH CH571576A patent/CH616053A5/de not_active IP Right Cessation
- 1976-05-07 TR TR18806A patent/TR18806A/xx unknown
- 1976-05-11 GR GR50685A patent/GR60312B/el unknown
- 1976-05-11 EG EG282/76D patent/EG12223A/xx active
- 1976-05-12 CS CS763177A patent/CS188137B2/cs unknown
- 1976-05-12 DD DD192808A patent/DD127521A5/xx unknown
- 1976-05-12 IT IT49436/76A patent/IT1061275B/it active
- 1976-05-12 LU LU74929A patent/LU74929A1/xx unknown
- 1976-05-12 IL IL49564A patent/IL49564A/xx unknown
- 1976-05-13 NZ NZ180854A patent/NZ180854A/xx unknown
- 1976-05-13 ES ES447867A patent/ES447867A1/es not_active Expired
- 1976-05-13 JP JP51054803A patent/JPS6030282B2/ja not_active Expired
- 1976-05-13 BE BE167009A patent/BE841804A/xx not_active IP Right Cessation
- 1976-05-13 AR AR263278A patent/AR217054A1/es active
- 1976-05-13 CA CA252,511A patent/CA1070239A/en not_active Expired
- 1976-05-13 GB GB19822/76A patent/GB1518562A/en not_active Expired
- 1976-05-13 SE SE7605473A patent/SE436679B/xx unknown
- 1976-05-13 ZA ZA00762872A patent/ZA762872B/xx unknown
- 1976-05-13 DK DK215376A patent/DK215376A/da unknown
- 1976-05-13 NL NLAANVRAGE7605105,A patent/NL185320C/xx not_active IP Right Cessation
- 1976-05-13 AU AU13908/76A patent/AU506400B2/en not_active Expired
- 1976-05-14 BR BR7603059A patent/BR7603059A/pt unknown
- 1976-05-14 FR FR7614627A patent/FR2310701A1/fr active Granted
- 1976-05-14 MX MX76237U patent/MX4390E/es unknown
- 1976-05-14 IE IE1033/76A patent/IE43688B1/en unknown
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
8110 | Request for examination paragraph 44 | ||
8126 | Change of the secondary classification |
Ipc: A01N 43/48 |
|
8125 | Change of the main classification |
Ipc: A01N 43/60 |
|
D2 | Grant after examination | ||
8364 | No opposition during term of opposition | ||
8327 | Change in the person/name/address of the patent owner |
Owner name: SHELL AGRAR GMBH & CO KG, 6507 INGELHEIM, DE |
|
8327 | Change in the person/name/address of the patent owner |
Owner name: SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V., D |
|
8328 | Change in the person/name/address of the agent |
Free format text: JUNG, E., DIPL.-CHEM. DR.PHIL. SCHIRDEWAHN, J., DIPL.-PHYS. DR.RER.NAT. GERNHARDT, C., DIPL.-ING., PAT.-ANWAELTE, 8000 MUENCHEN |