CS199724B2 - Growth plants regulator and process for preparing effective compounds - Google Patents
Growth plants regulator and process for preparing effective compounds Download PDFInfo
- Publication number
- CS199724B2 CS199724B2 CS222178A CS222178A CS199724B2 CS 199724 B2 CS199724 B2 CS 199724B2 CS 222178 A CS222178 A CS 222178A CS 222178 A CS222178 A CS 222178A CS 199724 B2 CS199724 B2 CS 199724B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- methyl
- dimethylphenyl
- active ingredient
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 48
- 230000012010 growth Effects 0.000 title description 9
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 15
- 150000001450 anions Chemical class 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 230000008635 plant growth Effects 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims description 25
- -1 p-toluenesulfonate ion Chemical group 0.000 claims description 24
- CAHSMZHNMDHDTB-UHFFFAOYSA-N dimethylsulfanium methyl sulfate Chemical compound C[SH+]C.COS([O-])(=O)=O CAHSMZHNMDHDTB-UHFFFAOYSA-N 0.000 claims description 22
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 14
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- BPPUNZFQQROEGL-UHFFFAOYSA-N dimethylsulfanium;4-methylbenzenesulfonate Chemical compound C[SH+]C.CC1=CC=C(S([O-])(=O)=O)C=C1 BPPUNZFQQROEGL-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005527 methyl sulfate group Chemical group 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 abstract description 3
- 230000001105 regulatory effect Effects 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 241000196324 Embryophyta Species 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 244000068988 Glycine max Species 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 7
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- 238000002360 preparation method Methods 0.000 description 6
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- 235000003222 Helianthus annuus Nutrition 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 244000299507 Gossypium hirsutum Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 244000038559 crop plants Species 0.000 description 4
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 4
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 230000033228 biological regulation Effects 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000000197 pyrolysis Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
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- 238000005507 spraying Methods 0.000 description 3
- 230000009105 vegetative growth Effects 0.000 description 3
- JSYBJWAZPHAASJ-UHFFFAOYSA-N 2,4,5-trimethylbenzenethiol Chemical compound CC1=CC(C)=C(S)C=C1C JSYBJWAZPHAASJ-UHFFFAOYSA-N 0.000 description 2
- BSYMCBXJESUTTH-UHFFFAOYSA-N 2,5-dimethyl-4-methylsulfanylphenol Chemical compound CSC1=CC(C)=C(O)C=C1C BSYMCBXJESUTTH-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- 101100203496 Arabidopsis thaliana SMO2-1 gene Proteins 0.000 description 2
- 101100312823 Arabidopsis thaliana TRM112A gene Proteins 0.000 description 2
- 241000208818 Helianthus Species 0.000 description 2
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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- 229910021183 SMO2 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 102100029540 Structural maintenance of chromosomes protein 2 Human genes 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 150000002367 halogens Chemical group 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
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- 239000007788 liquid Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 229960000790 thymol Drugs 0.000 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 description 2
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- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
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- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- SOOARYARZPXNAL-UHFFFAOYSA-N methyl-thiophenol Natural products CSC1=CC=CC=C1O SOOARYARZPXNAL-UHFFFAOYSA-N 0.000 description 1
- XMWFMEYDRNJSOO-UHFFFAOYSA-N morpholine-4-carbonyl chloride Chemical compound ClC(=O)N1CCOCC1 XMWFMEYDRNJSOO-UHFFFAOYSA-N 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- CTYRPMDGLDAWRQ-UHFFFAOYSA-N phenyl hydrogen sulfate Chemical compound OS(=O)(=O)OC1=CC=CC=C1 CTYRPMDGLDAWRQ-UHFFFAOYSA-N 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000021251 pulses Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000026267 regulation of growth Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical group CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- XDLNRRRJZOJTRW-UHFFFAOYSA-N thiohypochlorous acid Chemical compound ClS XDLNRRRJZOJTRW-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
-
- 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
- A01N47/22—O-Aryl or S-Aryl esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
- C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB14243/77A GB1593541A (en) | 1977-04-05 | 1977-04-05 | Carbamate esters of hydroxyaryl sulphonium salts and methods of regulating plant growth employing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS199724B2 true CS199724B2 (en) | 1980-07-31 |
Family
ID=10037633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS222178A CS199724B2 (en) | 1977-04-05 | 1979-10-31 | Growth plants regulator and process for preparing effective compounds |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4221582A (de) |
| JP (1) | JPS53124236A (de) |
| AR (1) | AR223144A1 (de) |
| AT (1) | AT358607B (de) |
| AU (1) | AU519274B2 (de) |
| BR (1) | BR7802073A (de) |
| CS (1) | CS199724B2 (de) |
| DE (1) | DE2814453A1 (de) |
| ES (1) | ES468532A1 (de) |
| FR (1) | FR2386522A1 (de) |
| GB (1) | GB1593541A (de) |
| IT (1) | IT1102571B (de) |
| NL (1) | NL7803617A (de) |
| TR (1) | TR19956A (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT7949744A0 (it) * | 1978-07-31 | 1979-07-13 | Sandoz Ag | Sali di solfonio loro preparazione e loro applicazione come medicamenti(caso 600-6791/x) |
| JPH01226868A (ja) * | 1988-03-08 | 1989-09-11 | Sanshin Kagaku Kogyo Kk | スルホニウム化合物及びアシル化剤 |
| JP2809883B2 (ja) * | 1994-09-22 | 1998-10-15 | ユコン リミテッド | 新規のカルバメート化合物及びその製造方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3133947A (en) * | 1959-09-16 | 1964-05-19 | Stanffer Chemical Company | Preparation of esters of thiolcarbamic acids |
| NL279203A (de) * | 1961-06-02 | |||
| US3235356A (en) * | 1962-06-29 | 1966-02-15 | Crown Zellerbach Corp | Method of controlling growth of plants |
| US3282979A (en) * | 1963-06-17 | 1966-11-01 | Dow Chemical Co | Phenolic thioethers |
| US3784563A (en) * | 1968-09-04 | 1974-01-08 | Baychem Corp | Carbamic acid esters of polyhalo disulfide alcohols |
| US3652255A (en) * | 1969-09-03 | 1972-03-28 | Basf Ag | Agents for retarding the growth of plants and changing their habit |
| US3834888A (en) * | 1970-06-16 | 1974-09-10 | Ici Ltd | Plant growth regulating compositions comprising 2-(s,s-dihydrocarbyl)sulphonium ethane phosphonic acid compounds as active component |
| IL41839A (en) * | 1972-04-13 | 1975-04-25 | Basf Ag | The use of cyclic sulfonium salts for regulating plant growth |
| JPS5063135A (de) * | 1974-03-27 | 1975-05-29 | ||
| IT1054168B (it) * | 1974-06-07 | 1981-11-10 | Montedison Spa | Addotti cristallini a rapporto molare 1.3 fra carbamoil solfossidi e urea |
| JPS5115627A (ja) * | 1974-07-26 | 1976-02-07 | Nissan Chemical Ind Ltd | Shokubutsuseiikuyokuseizai |
-
1977
- 1977-04-05 GB GB14243/77A patent/GB1593541A/en not_active Expired
-
1978
- 1978-04-03 US US05/892,558 patent/US4221582A/en not_active Expired - Lifetime
- 1978-04-04 IT IT48729/78A patent/IT1102571B/it active
- 1978-04-04 DE DE19782814453 patent/DE2814453A1/de not_active Withdrawn
- 1978-04-04 BR BR7802073A patent/BR7802073A/pt unknown
- 1978-04-04 AU AU34769/78A patent/AU519274B2/en not_active Expired
- 1978-04-04 ES ES468532A patent/ES468532A1/es not_active Expired
- 1978-04-05 AR AR271692A patent/AR223144A1/es active
- 1978-04-05 AT AT239678A patent/AT358607B/de not_active IP Right Cessation
- 1978-04-05 JP JP4015278A patent/JPS53124236A/ja active Pending
- 1978-04-05 FR FR7810127A patent/FR2386522A1/fr active Granted
- 1978-04-05 NL NL7803617A patent/NL7803617A/xx not_active Application Discontinuation
-
1979
- 1979-04-05 TR TR19956A patent/TR19956A/xx unknown
- 1979-10-31 CS CS222178A patent/CS199724B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2386522B1 (de) | 1982-04-16 |
| TR19956A (tr) | 1980-05-15 |
| AU3476978A (en) | 1979-10-11 |
| AU519274B2 (en) | 1981-11-19 |
| DE2814453A1 (de) | 1978-10-19 |
| IT7848729A0 (it) | 1978-04-04 |
| ES468532A1 (es) | 1979-09-16 |
| GB1593541A (en) | 1981-07-15 |
| FR2386522A1 (fr) | 1978-11-03 |
| AT358607B (de) | 1980-09-25 |
| IT1102571B (it) | 1985-10-07 |
| US4221582A (en) | 1980-09-09 |
| BR7802073A (pt) | 1978-12-19 |
| JPS53124236A (en) | 1978-10-30 |
| ATA239678A (de) | 1980-02-15 |
| AR223144A1 (es) | 1981-07-31 |
| NL7803617A (nl) | 1978-10-09 |
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