GB772731A - New pesticidal compositions containing phosphorus esters - Google Patents
New pesticidal compositions containing phosphorus estersInfo
- Publication number
- GB772731A GB772731A GB80954A GB80954A GB772731A GB 772731 A GB772731 A GB 772731A GB 80954 A GB80954 A GB 80954A GB 80954 A GB80954 A GB 80954A GB 772731 A GB772731 A GB 772731A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphorothiolate
- diethyl
- aqueous solution
- solution
- 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
- 239000000203 mixture Substances 0.000 title abstract 12
- 230000000361 pesticidal effect Effects 0.000 title abstract 4
- 150000003017 phosphorus Chemical class 0.000 title 1
- -1 alkyl radicals Chemical class 0.000 abstract 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 11
- 239000007864 aqueous solution Substances 0.000 abstract 11
- 239000000243 solution Substances 0.000 abstract 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 abstract 8
- 150000003839 salts Chemical class 0.000 abstract 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 abstract 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- 150000002148 esters Chemical class 0.000 abstract 6
- 235000015097 nutrients Nutrition 0.000 abstract 6
- 125000001931 aliphatic group Chemical group 0.000 abstract 5
- 238000002360 preparation method Methods 0.000 abstract 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 abstract 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 4
- 239000004202 carbamide Substances 0.000 abstract 4
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 abstract 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-M 3-carboxy-2-(carboxymethyl)-2-hydroxypropanoate Chemical compound OC(=O)CC(O)(C(O)=O)CC([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-M 0.000 abstract 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 150000003254 radicals Chemical class 0.000 abstract 3
- 229920006395 saturated elastomer Polymers 0.000 abstract 3
- 239000007787 solid Substances 0.000 abstract 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 2
- 239000012752 auxiliary agent Substances 0.000 abstract 2
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 abstract 2
- 239000000969 carrier Substances 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 abstract 2
- PHHWLDOIMGFHOZ-UHFFFAOYSA-L disodium;dinaphthalen-1-ylmethanedisulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)(S(=O)(=O)[O-])S([O-])(=O)=O)=CC=CC2=C1 PHHWLDOIMGFHOZ-UHFFFAOYSA-L 0.000 abstract 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 abstract 2
- 235000019341 magnesium sulphate Nutrition 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 abstract 1
- 239000004141 Sodium laurylsulphate Substances 0.000 abstract 1
- 230000000895 acaricidal effect Effects 0.000 abstract 1
- 239000000440 bentonite Substances 0.000 abstract 1
- 229910000278 bentonite Inorganic materials 0.000 abstract 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 abstract 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 abstract 1
- 229910000397 disodium phosphate Inorganic materials 0.000 abstract 1
- 235000019800 disodium phosphate Nutrition 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 238000010410 dusting Methods 0.000 abstract 1
- 239000003292 glue Substances 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 150000002484 inorganic compounds Chemical class 0.000 abstract 1
- 229910010272 inorganic material Inorganic materials 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 238000004806 packaging method and process Methods 0.000 abstract 1
- 230000001931 phytocidal effect Effects 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 238000009738 saturating Methods 0.000 abstract 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 abstract 1
- 239000001488 sodium phosphate Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007921 spray Substances 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- 231100000331 toxic Toxicity 0.000 abstract 1
- 230000002588 toxic effect Effects 0.000 abstract 1
- 238000009736 wetting Methods 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F04—POSITIVE - DISPLACEMENT MACHINES FOR LIQUIDS; PUMPS FOR LIQUIDS OR ELASTIC FLUIDS
- F04C—ROTARY-PISTON, OR OSCILLATING-PISTON, POSITIVE-DISPLACEMENT MACHINES FOR LIQUIDS; ROTARY-PISTON, OR OSCILLATING-PISTON, POSITIVE-DISPLACEMENT PUMPS
- F04C2210/00—Fluid
- F04C2210/26—Refrigerants with particular properties, e.g. HFC-134a
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Examples are given for the preparation of certain salts of phosphorothiolic acid esters of the general formula O = P(OR1)(OR2)-S-LX in which R1 and R2 are like or unlike alkyl radicals, L is a saturated straight or branched chain aliphatic hydrocarbon radical or such a radical in which the carbon atoms are interrupted by an oxygen or sulphur atom or by a nitrogen atom carrying an alkyl substituent and X is a secondary aliphatic or heterocyclic amine attached to L through the amino nitrogen atom, said salts being used in pesticidal compositions (see Groups I and VI). In the examples: (1) the p-toluene sulphonate of O,O1-diethyl S-b -diethylaminoethyl phosphorothiolate is obtained by adding a mixture of the phosphorothiolate and diethyl ether to a solution of p-toluenesulphonic acid in ether, the salt being precipitated; (2) and (3) the hydrogen oxalate salt and the dihydrogen citrate salt respectively of the same phosphorothiolate are obtained by adding a mixture of the phosphorothiolate and methanol to oxalic acid dihydrate (or citric acid) in methanol and concentrating the resulting solution; (4) the hydrogen oxalate of O,O1-diethyl-S-1-diethyl-amino-prop-2-yl phosphorothiolate is obtained by treating the phosphorothiolate with a solution of oxalic acid dihydrate in acetone and allowing the salt to precipitate; (5) O,O1-diethyl-S-b -piperidinoethyl phosphorothiolate hydrogen oxalate is obtained by adding a solution of the phosphorothiolate in acetone to a solution of oxalic acid dihydrate in acetone, the salt being precipitated; (6) O,O1 - diethyl S - b - morpholinoethyl phosphorothiolate p-toluene-sulphonate is obtained by adding a solution of the phosphorothiolate in ether to a solution of p-toluene sulphonic acid in ether; (7) O,O1-diethyl S-b -di-n-propylaminoethyl phosphorothiolate hydrogen oxalate is obtained by treating the ester with a solution of oxalic acid dihydrate in acetone; (8) O,O1-diethyl - S - b - diethylaminoethyl phosphorothiolate hydrochloride is obtained by saturating a solution of the ester in ether with dry hydrogen chloride and removing the solvent and excess hydrogen chloride under reduced pressure. Specification 738,839 is referred to.ALSO:A pesticidal plant nutrient composition comprises a phosphorothiolic acid ester of the general formula: O = P(OR1)(OR2)-S-LX in which R1 and R2 are like or unlike alkyl radicals, L is a saturated straight or branched chain aliphatic hydrocarbon radical or such a radical in which the carbon atoms are interrupted by an oxygen or sulphur atom or by a nitrogen atom carrying an alkyl substituent and X is a secondary aliphatic or heterocyclic amine attached to L through the amino nitrogen atom or a salt of such aliphatic or heterocyclic amine, and a plant nutrient (see also Group VI). Specified plant nutrients are urea and magnesium sulphate. In an example a mixture of urea with a small amount of O,O1-diethyl S-b -diethylamino ethyl phosphorothiolate dihydrogen citrate (see Group IV(b), is dissolved in water to give a combined acaricidal and nutrient spray. Alternatively the mixture can be compressed into granules, tablets or briquettes for convenience in handling, packaging, storing and measuring. Specification 738,839 [Group IV(b)] is referred to.ALSO:Pesticidal compositions comprise a phosphorothiolic acid ester of the general formula:-O=P(OR1)(OR2)-S-LX in which R1 and R2 are like or unlike alkyl radicals, L is a saturated straight or branched chain aliphatic hydrocarbon radical or such a radical in which the carbon atoms are interrupted by an oxygen or sulphur atom or by a nitrogen atom carrying an alkyl substituent and X is a secondary aliphatic or heterocyclic amine or a salt of such aliphatic or heterocyclic amine and a carrier and if desired an auxiliary agent and/or a plant nutrient. As carriers there may be used liquids e.g. water or non-phytocidal organic solvents or solids e.g. talc, keiselguhr, bentonite and other colloidal clays and powdered chalk. For concentrated solid preparations there may be used other solid carriers particularly water-soluble organic and inorganic compounds and the toxic ingredient may be incorporated with these to give a shaped tablet or block or a non-hygroscopic free-flowing granular preparation. Specified auxiliary agents are dustbinding agents such as spindle oil, glycerol, and wool fat. Wetting, spreading and dispersing agents such as sodium dinaphthylmethane disulphonate and sodium lauryl sulphate and sticking agents such as glue and resin may also be used especially in liquid preparations. Specified plant nutrients are urea and magnesium sulphate. Examples are given of the following compositions: (1) one part of O : O1 - diethyl - S - b - diethylamino - ethyl phosphorothiolate dissolved in 2000 parts of water also 1 part of O - ethyl O1 - methyl S - b - diethylaminoethyl phosphorothiolate dissolved in 50,000 parts of water, (2) a 0.002 per cent aqueous solution of the p.toluene sulphonate salt of O, O1-diethyl S-b -diethylaminoethyl phosphorothiolate; (3) an aqueous solution of the hydrogen oxalate of O, O1-diethyl S-b -diethylaminoethyl phosphorothiolate (4) an aqueous solution of O, O1-diethyl S-b -diethylamino ethyl phosphorothiolate dihydrogen citrate; (5) an aqueous solution of the hydrogen oxalate of O, O1-diethyl S-1-diethylamino prop-2-yl phosphorothiolate; (6) an aqueous solution of O, O1 - diethyl - S - b - piperidinoethyl phosphorothiolate hydrogen oxalate; (7) an aqueous solution of O : O1 - diethyl - S-b -morpholinoethyl phosphorothiolate p-toluene sulphonate; (8) an aqueous solution of O : O1-diethyl S-b -di-n-propylamino phosphorothiolate hydrogen oxalate; (9) an aqueous solution of a mixture of urea and a small amount of O : O1-diethyl S-b -diethylaminoethyl phosphorothiolate dihydrogen citrate; (10) an aqueous solution formed by dissolving O : O1-diethyl S-b -di-ethyl-amino-ethyl phosphorothiolate, citric acid and disodium phosphate in a large excess of water; (11) O : O1-diethyl-S-b -diethyl-aminoethyl phosphorothiolate dissolved in diacetone alcohol; (12) a non-dusting pulverulent composition formed by mixing O : O1-diethyl S-b -diethylaminoethyl phosphorothiolate with kieselguhr and spindle oil; (13) an aqueous solution of a mixture of sodium dinaphthylmethane disulphonate and a small amount of O : O1-diethyl S-b -piperidinoethyl phosphorothiolate or its hydrogen oxalate; (14) an aqueous solution of O : O1-diethyl S - b - diethyl-aminoethyl phosphorothiolate hydrochloride. The preparation of the specified salts of the phosphorothiolate esters is described (see Group IV(b)). Specification 738,839 [Group IV(b)] is referred to.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE534788D BE534788A (en) | 1954-01-11 | ||
| GB80954A GB772731A (en) | 1954-01-11 | 1954-01-11 | New pesticidal compositions containing phosphorus esters |
| ES0219377A ES219377A1 (en) | 1954-01-11 | 1955-01-05 | New pesticidal compositions containing phosphorus esters |
| US481032A US2841517A (en) | 1954-01-11 | 1955-01-10 | Phosphorothiolic acid ester compositions and methods of destroying insects |
| FR1119292D FR1119292A (en) | 1954-01-11 | 1955-01-11 | Insecticides containing phosphorus esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB80954A GB772731A (en) | 1954-01-11 | 1954-01-11 | New pesticidal compositions containing phosphorus esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB772731A true GB772731A (en) | 1957-04-17 |
Family
ID=9710879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB80954A Expired GB772731A (en) | 1954-01-11 | 1954-01-11 | New pesticidal compositions containing phosphorus esters |
Country Status (2)
| Country | Link |
|---|---|
| ES (1) | ES219377A1 (en) |
| GB (1) | GB772731A (en) |
-
1954
- 1954-01-11 GB GB80954A patent/GB772731A/en not_active Expired
-
1955
- 1955-01-05 ES ES0219377A patent/ES219377A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES219377A1 (en) | 1955-03-01 |
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