DE1768815B1 - Verwendung von alkylsubstituierten 2-(2-Chlor-2-cyanaethyl)-benzolen als Mittel zur Regelung des Pflanzenwachstums - Google Patents
Verwendung von alkylsubstituierten 2-(2-Chlor-2-cyanaethyl)-benzolen als Mittel zur Regelung des PflanzenwachstumsInfo
- Publication number
- DE1768815B1 DE1768815B1 DE19681768815 DE1768815A DE1768815B1 DE 1768815 B1 DE1768815 B1 DE 1768815B1 DE 19681768815 DE19681768815 DE 19681768815 DE 1768815 A DE1768815 A DE 1768815A DE 1768815 B1 DE1768815 B1 DE 1768815B1
- Authority
- DE
- Germany
- Prior art keywords
- chloro
- cyanoethyl
- benzenes
- chlorotoluene
- substituted
- 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.)
- Withdrawn
Links
- 230000008635 plant growth Effects 0.000 title claims description 7
- 230000001105 regulatory effect Effects 0.000 title claims description 6
- ZUPBNBYEVVGQKK-UHFFFAOYSA-N 2-chloro-3-phenylpropanenitrile Chemical class N#CC(Cl)CC1=CC=CC=C1 ZUPBNBYEVVGQKK-UHFFFAOYSA-N 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 description 17
- -1 2- (2-chloro-2-cyanoethyl) -4-chlorotoluene Chemical compound 0.000 description 16
- YYJUXSGXHHPBTK-UHFFFAOYSA-N 2-chloro-3-(3-chloro-2-methylphenyl)propanenitrile Chemical compound CC1=C(Cl)C=CC=C1CC(Cl)C#N YYJUXSGXHHPBTK-UHFFFAOYSA-N 0.000 description 14
- 239000000839 emulsion Substances 0.000 description 14
- 239000013543 active substance Substances 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 7
- 240000003768 Solanum lycopersicum Species 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- OPHVSASGPNDWOP-UHFFFAOYSA-N 4-amino-2-(dimethylamino)-4-oxobutanoic acid Chemical compound CN(C)C(C(O)=O)CC(N)=O OPHVSASGPNDWOP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 235000016068 Berberis vulgaris Nutrition 0.000 description 4
- 241000335053 Beta vulgaris Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 240000007087 Apium graveolens Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 238000007192 Meerwein reaction reaction Methods 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000208181 Pelargonium Species 0.000 description 2
- 235000002560 Solanum lycopersicum Nutrition 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 230000005071 geotropism Effects 0.000 description 2
- 238000003306 harvesting Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 1
- WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical compound CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 description 1
- 235000002764 Apium graveolens Nutrition 0.000 description 1
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 1
- 235000010591 Appio Nutrition 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- 241000208150 Geraniaceae Species 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 235000017276 Salvia Nutrition 0.000 description 1
- 240000007164 Salvia officinalis Species 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000002942 anti-growth Effects 0.000 description 1
- 239000001387 apium graveolens Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001609 comparable effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000459 effect on growth Effects 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 239000004563 wettable powder 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE701102 | 1967-07-07 | ||
| BE45980 | 1967-07-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1768815B1 true DE1768815B1 (de) | 1971-08-12 |
Family
ID=25647297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681768815 Withdrawn DE1768815B1 (de) | 1967-07-07 | 1968-07-03 | Verwendung von alkylsubstituierten 2-(2-Chlor-2-cyanaethyl)-benzolen als Mittel zur Regelung des Pflanzenwachstums |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3671217A (enExample) |
| BE (1) | BE701102A (enExample) |
| CH (1) | CH515676A (enExample) |
| DE (1) | DE1768815B1 (enExample) |
| FR (1) | FR1573444A (enExample) |
| GB (1) | GB1223894A (enExample) |
| NL (1) | NL6809094A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001655A3 (en) * | 1977-10-17 | 1979-05-16 | Shell Internationale Researchmaatschappij B.V. | Compositions comprising as active ingredients cyanobenzyl(idene)-aniline derivatives, the use of the compositions as plant growth regulants and a method for the preparation of the active ingredients |
-
1967
- 1967-07-07 BE BE701102D patent/BE701102A/xx not_active IP Right Cessation
-
1968
- 1968-06-27 NL NL6809094A patent/NL6809094A/xx unknown
- 1968-07-03 CH CH1001768A patent/CH515676A/fr not_active IP Right Cessation
- 1968-07-03 GB GB31804/68A patent/GB1223894A/en not_active Expired
- 1968-07-03 FR FR1573444D patent/FR1573444A/fr not_active Expired
- 1968-07-03 DE DE19681768815 patent/DE1768815B1/de not_active Withdrawn
- 1968-07-05 US US742512A patent/US3671217A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1573444A (enExample) | 1969-07-04 |
| GB1223894A (en) | 1971-03-03 |
| BE701102A (enExample) | 1968-01-08 |
| CH515676A (fr) | 1971-11-30 |
| US3671217A (en) | 1972-06-20 |
| NL6809094A (enExample) | 1969-01-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |