DE1915327A1 - AEthinylenhaltige N-Phenylcarbamate und ihre Verwendung als Acarizide und Insektizide - Google Patents
AEthinylenhaltige N-Phenylcarbamate und ihre Verwendung als Acarizide und InsektizideInfo
- Publication number
- DE1915327A1 DE1915327A1 DE19691915327 DE1915327A DE1915327A1 DE 1915327 A1 DE1915327 A1 DE 1915327A1 DE 19691915327 DE19691915327 DE 19691915327 DE 1915327 A DE1915327 A DE 1915327A DE 1915327 A1 DE1915327 A1 DE 1915327A1
- Authority
- DE
- Germany
- Prior art keywords
- butyne
- group
- radical
- acaricides
- hydrogen atom
- 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
- 230000000895 acaricidal effect Effects 0.000 title claims description 10
- 239000000642 acaricide Substances 0.000 title claims description 9
- 239000002917 insecticide Substances 0.000 title claims description 5
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 title description 3
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 title description 2
- -1 alkyl radical Chemical class 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 241000238876 Acari Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 230000012447 hatching Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
- 241000239290 Araneae Species 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
- 241000254173 Coleoptera Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000021501 Rumex crispus Nutrition 0.000 description 1
- 244000207667 Rumex vesicarius Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- NEEDEQSZOUAJMU-UHFFFAOYSA-N but-2-yn-1-ol Chemical compound CC#CCO NEEDEQSZOUAJMU-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 231100000194 ovacidal Toxicity 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 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
- 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
- A01N47/20—N-Aryl derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71797068A | 1968-04-01 | 1968-04-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1915327A1 true DE1915327A1 (de) | 1969-10-23 |
Family
ID=24884268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691915327 Pending DE1915327A1 (de) | 1968-04-01 | 1969-03-26 | AEthinylenhaltige N-Phenylcarbamate und ihre Verwendung als Acarizide und Insektizide |
Country Status (9)
| Country | Link |
|---|---|
| AT (2) | AT299617B (fr) |
| BE (1) | BE726244A (fr) |
| CH (1) | CH475708A (fr) |
| DE (1) | DE1915327A1 (fr) |
| ES (1) | ES362623A1 (fr) |
| FR (1) | FR2005230A1 (fr) |
| GB (1) | GB1246722A (fr) |
| IL (1) | IL31392A0 (fr) |
| NL (1) | NL6900428A (fr) |
-
1968
- 1968-12-30 BE BE726244D patent/BE726244A/xx unknown
-
1969
- 1969-01-09 IL IL31392A patent/IL31392A0/xx unknown
- 1969-01-10 NL NL6900428A patent/NL6900428A/xx unknown
- 1969-01-14 AT AT376470A patent/AT299617B/de not_active IP Right Cessation
- 1969-01-14 AT AT36169A patent/AT292011B/de not_active IP Right Cessation
- 1969-01-17 ES ES362623A patent/ES362623A1/es not_active Expired
- 1969-01-23 GB GB3770/69A patent/GB1246722A/en not_active Expired
- 1969-01-31 FR FR6902193A patent/FR2005230A1/fr not_active Withdrawn
- 1969-03-26 DE DE19691915327 patent/DE1915327A1/de active Pending
- 1969-04-01 CH CH501569A patent/CH475708A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL6900428A (fr) | 1969-10-03 |
| CH475708A (de) | 1969-07-31 |
| AT292011B (de) | 1971-08-10 |
| GB1246722A (en) | 1971-09-15 |
| FR2005230A1 (fr) | 1969-12-12 |
| AT299617B (de) | 1972-06-26 |
| ES362623A1 (es) | 1970-11-16 |
| BE726244A (fr) | 1969-06-30 |
| IL31392A0 (en) | 1969-03-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2111414A1 (de) | Insektizide Mittel | |
| DE1803084A1 (de) | Schaedlingsbekaempfungsmittel | |
| DE2654331C2 (fr) | ||
| DE2654314C2 (fr) | ||
| DE2206011A1 (de) | 1-acyl-3-aminosulfonyl-2-imino-benzimidazoline, verfahren zu ihrer herstellung und ihre fungizide verwendung | |
| DE2743633A1 (de) | Neue bicarbamoylsulfide, ihre herstellung und die sie enthaltenden mittel | |
| DE2462422A1 (de) | 2-carbamoyloximino-1,4-oxathiacyclohexane sowie deren 4-oxide und 4,4-dioxide und verfahren zu deren herstellung | |
| DE2813281C2 (de) | N-substituierte Bis-Carbamoyloximinodisulfidverbindungen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Pestizide | |
| EP0109600B1 (fr) | Ester d'acide chloro-3-phényl-3-propène-2-énylthiophosphorique, son procédé de préparation et son utilisation comme pesticide | |
| DE2630912C2 (fr) | ||
| DE1915327A1 (de) | AEthinylenhaltige N-Phenylcarbamate und ihre Verwendung als Acarizide und Insektizide | |
| DE2061133A1 (de) | Pestizide Verbindung,Verfahren zu ihrer Herstellung und Verwendung | |
| DE2813374C2 (de) | Carbamat-thiosulfenylcarbamoylfluoridverbindungen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Pestizide | |
| EP0114625B1 (fr) | Esters 0,S-dialcoyl-S-(carbamoyloxyméthyliques)-d'acide dithiophosphorique, leur procédé de préparation ainsi que leur utilisation comme pesticides | |
| DE2249939A1 (de) | Phosphorsaeureester | |
| US3792168A (en) | Ethynylene containing n-phenyl carbamates and their use as acaricides and insecticides | |
| AT365412B (de) | Insektizid, nematizid und akarizid wirksames mittel | |
| AT362197B (de) | Verfahren zur bekaempfung von insekten, milben und nematoden | |
| DE2111589A1 (de) | Insektizide Mittel | |
| AT240870B (de) | Verfahren zur Herstellung von neuen, beispielsweise zur Schädlingsbekämpfung verwendbaren α-Oxy-β,β,β-trichloräthylphosphonsäureestern | |
| DE1768041C3 (de) | ß-Alkoxyacrylsaureamide und deren Verwendung zur Bekämpfung von Insekten und Akariden | |
| AT339662B (de) | Insektizide, akarizide und nematizide mittel | |
| DE2016678A1 (de) | Carbo-beta-Fluoräthoxyverbindungen, ihre Herstellung und ihre Verwendung in Schädlingsbekämpfungsmitteln | |
| DE2316733A1 (de) | Dithio- und trithiophosphonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematozide | |
| DE2243612A1 (de) | Thiophen-glyoxylonitril-oxim-phosphorsaeurederivate und ihre verwendung |