RU2619948C1 - N1,n1,n4,n4-tetramethyl-2-butyne-1,4-diamine salt with n-phosphonomethylglycine, showing herbicid activity and the method of its production - Google Patents
N1,n1,n4,n4-tetramethyl-2-butyne-1,4-diamine salt with n-phosphonomethylglycine, showing herbicid activity and the method of its production Download PDFInfo
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- RU2619948C1 RU2619948C1 RU2016120787A RU2016120787A RU2619948C1 RU 2619948 C1 RU2619948 C1 RU 2619948C1 RU 2016120787 A RU2016120787 A RU 2016120787A RU 2016120787 A RU2016120787 A RU 2016120787A RU 2619948 C1 RU2619948 C1 RU 2619948C1
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- phosphonomethylglycine
- tetramethyl
- butyne
- diamine
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- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 4
- FFDFQBBNDKGBGI-UHFFFAOYSA-N n,n,n',n'-tetramethylbut-2-yne-1,4-diamine Chemical class CN(C)CC#CCN(C)C FFDFQBBNDKGBGI-UHFFFAOYSA-N 0.000 title abstract description 4
- 230000000694 effects Effects 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 8
- 241000196324 Embryophyta Species 0.000 claims abstract description 6
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- JKFHONMXWKNXAL-UHFFFAOYSA-N 1-n,1-n,4-n-trimethylpent-2-yne-1,4-diamine Chemical compound CNC(C)C#CCN(C)C JKFHONMXWKNXAL-UHFFFAOYSA-N 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 description 7
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 240000000073 Achillea millefolium Species 0.000 description 1
- 235000007754 Achillea millefolium Nutrition 0.000 description 1
- 235000005637 Brassica campestris Nutrition 0.000 description 1
- 235000014750 Brassica kaber Nutrition 0.000 description 1
- 240000008100 Brassica rapa Species 0.000 description 1
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 1
- 235000010570 Brassica rapa var. rapa Nutrition 0.000 description 1
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 1
- 240000001579 Cirsium arvense Species 0.000 description 1
- 235000005918 Cirsium arvense Nutrition 0.000 description 1
- 241000207894 Convolvulus arvensis Species 0.000 description 1
- 241000508725 Elymus repens Species 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 235000001018 Hibiscus sabdariffa Nutrition 0.000 description 1
- 244000042664 Matricaria chamomilla Species 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- 244000292693 Poa annua Species 0.000 description 1
- 235000005291 Rumex acetosa Nutrition 0.000 description 1
- 240000007001 Rumex acetosella Species 0.000 description 1
- 244000111146 Sonchus arvensis Species 0.000 description 1
- 235000008132 Sonchus arvensis ssp. uliginosus Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000003513 sheep sorrel Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000003595 spectral effect Effects 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/20—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
- C07C211/23—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton the carbon skeleton containing carbon-to-carbon triple bonds
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3813—N-Phosphonomethylglycine; Salts or complexes thereof
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- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Предлагаемая группа изобретений относится к новым химическим соединениям с биологической активностью, конкретно к соли N1,N1,N4,N4-тетраметил-2-бутин-1,4-диамина с N-фосфонометилглицином формулы (1) в качестве гербицида для борьбы с однолетними и многолетними однодольными и двудольными сорняками в сельском хозяйстве и способу ее получения.The proposed group of inventions relates to new chemical compounds with biological activity, specifically to a salt of N 1 , N 1 , N 4 , N 4- tetramethyl-2-butyn-1,4-diamine with N-phosphonomethylglycine of the formula (1) as a herbicide for control of annual and perennial monocotyledonous and dicotyledonous weeds in agriculture and the method of its production.
Известна изопропиламиновая соль N-фосфонометилглицина (2), проявляющая гербицидную активность (Мельников Н.Н., Новожилов К.В., Белан С.Р. Справочник пестициды и регуляторы роста растений. М.: Химия, 1995, С. 56).Known isopropylamine salt of N-phosphonomethylglycine (2), exhibiting herbicidal activity (Melnikov N.N., Novozhilov K.V., Belan S.R. Handbook of pesticides and plant growth regulators. M: Chemistry, 1995, S. 56).
Задачей предлагаемого изобретения является создание в ряду производных N-фосфонометилглицина новой алкинаминной соли, обладающей улучшенными гербицидными свойствами по отношению к однолетним и многолетним двудольным сорнякам, что может быть использовано в сельском хозяйстве.The objective of the invention is the creation of a series of N-phosphonomethylglycine derivatives of a new alkynamine salt having improved herbicidal properties with respect to annual and perennial dicotyledonous weeds, which can be used in agriculture.
Результат достигается тем, что в качестве водорастворимого фосфорорганического соединения, обладающего гербицидной активностью, создана соль N1,N1,N4,N4-тетраметил-1,4-диаминобутина с N-фосфонометилглицином формулы (1).The result is achieved in that a salt of N 1 , N 1 , N 4 , N 4- tetramethyl-1,4-diaminobutin with N-phosphonomethylglycine of the formula (1) is created as a water-soluble organophosphorus compound having herbicidal activity.
Способ получения соли N1,N1,N4,N4-тетраметил-2-бутин-1,4-диамина с N-фосфонометилглицином основан на перемешивании N1,N1,N4,N4-тетраметил-2-бутин-1,4-диамина (Джемилев У.М., Шайбакова М.Г., Махмудияров Г.А., Ибрагимов А.Г., Титова И.Г. Способ получения N1,N1,N4,N4-тетраметил-2-бутин-1,4-диамина. Патент РФ №2408572, опубл. 10.01.2011, бюл. №1) с эквимольным количеством водного раствора N-фосфонометилглицина при атмосферном давлении и предпочтительно при температуре 20-25°С в течение 2,5-3,0 часов. Выделяют водорастворимую соль N,N,N',N'-тетраметил-2-бутин-1,4-диамина с N-фосфонометилглицином формулы (1) с выходом 88-99%. Реакция протекает по схемеThe method for producing the salt of N 1 , N 1 , N 4 , N 4- tetramethyl-2-butyn-1,4-diamine with N-phosphonomethylglycine is based on the mixing of N 1 , N 1 , N 4 , N 4- tetramethyl-2-butine -1,4-diamine (Dzhemilev U.M., Shaybakova M.G., Makhmudiyarov G.A., Ibragimov A.G., Titova I.G. Method for producing N 1 , N 1 , N 4 , N 4 - tetramethyl-2-butyn-1,4-diamine. RF Patent No. 2408572, publ. 10.01.2011, bull. No. 1) with an equimolar amount of an aqueous solution of N-phosphonomethylglycine at atmospheric pressure and preferably at a temperature of 20-25 ° C for 2.5-3.0 hours. A water-soluble salt of N, N, N ', N'-tetramethyl-2-butyn-1,4-diamine with N-phosphonomethylglycine of the formula (1) is isolated in 88-99% yield. The reaction proceeds according to the scheme.
Спектральные характеристики соли N1,N1,N4,N4-тетраметил-2-бутин-1,4-диамина с N-фосфонометилглицином формулы (1):The spectral characteristics of the salts of N 1 , N 1 , N 4 , N 4- tetramethyl-2-butyn-1,4-diamine with N-phosphonomethylglycine of the formula (1):
Т.пл. 91-92°С. Спектр ЯМР 1Н (D2O, м.д.): 2.71 с ((А), 12Н, N(CH3)3); 2.96 д ((Б), 4Н, PCH2N JPH 12.8 Гц); 3.48 с ((А), 4Н, NCH2); 3.92 с ((Б), 4Н, NCH2); 4.72 уш. с ((Б), 8Н, ОН и NH).Mp 91-92 ° C. 1 H NMR Spectrum (D 2 O, ppm): 2.71 s ((A), 12H, N (CH 3 ) 3 ); 2.96 d ((B), 4H, PCH 2 NJ PH 12.8 Hz); 3.48 s ((A), 4H, NCH 2 ); 3.92 s ((B), 4H, NCH 2 ); 4.72 ears s ((B), 8H, OH and NH).
Спектр ЯМР 13С (D2O, м.д.): 41.97 ((А), С1,8,9,10); 43.06 и 44.42 ((Б), С2, JPC 136 Гц); 46.41 ((А), С3,6); 50.15 и 50.22 ((Б), С4, JPC 7 Гц); 78.64 ((А), С4,5); 170.75 ((Б), С5). ИК, см-1: 915 (О-Н); 1077 (C-N); 1171 (Р=O); 1324 (C-N); 1398 (C-N); 1633 (С=O); 2600-2645 (Р-ОН); 2933 (С-Н); 3418 (О-Н). Вычислено, %: С 35.15, Н 6.74, N 11.71, О 33.45, Р 12.95. Найдено, %: С 25.21, Н 6.37, N 7.74. C14H32N4O10P2. 13 C NMR Spectrum (D 2 O, ppm): 41.97 ((A), C 1,8,9,10 ); 43.06 and 44.42 ((B), C 2 , J PC 136 Hz); 46.41 ((A), C 3.6 ); 50.15 and 50.22 ((B), C 4 , J PC 7 Hz); 78.64 ((A), C 4.5 ); 170.75 ((B), C 5 ). IR, cm -1 : 915 (OH); 1077 (CN); 1171 (P = O); 1324 (CN); 1398 (CN); 1633 (C = O); 2600-2645 (P-OH); 2933 (C-H); 3418 (OH). Calculated,%: С 35.15, Н 6.74, N 11.71, О 33.45, Р 12.95. Found,%: C 25.21, H 6.37, N 7.74. C 14 H 32 N 4 O 10 P 2 .
Пример 1. В колбу с водным раствором, содержащим 169 г N-фосфонометилглицина, добавляют 116 г порошка N1,N1,N4,N4-тетраметил-2-бутин-1,4-диамина. Смесь перемешивают стеклянной мешалкой при атмосферном давлении и температуре 20°С в течение 2,5 часа, после чего определяют выход целевого продукта. Он составил 88%.Example 1. In a flask with an aqueous solution containing 169 g of N-phosphonomethylglycine, add 116 g of powder of N 1 , N 1 , N 4 , N 4- tetramethyl-2-butyn-1,4-diamine. The mixture is stirred with a glass stirrer at atmospheric pressure and a temperature of 20 ° C for 2.5 hours, after which the yield of the target product is determined. It amounted to 88%.
Пример 2. Аналогичным образом по примеру 1 при тех же условиях и аналогичной загрузке при перемешивании в течение 3 часов определяют выход целевого продукта. Он составил 93%.Example 2. In the same way as in example 1 under the same conditions and the same load with stirring for 3 hours determine the yield of the target product. It amounted to 93%.
Пример 3. Аналогичным образом по примеру 1 при той же загрузке компонентов проводят реакцию в течение 3 часов при температуре 22°С. Выход целевого продукта составляет 97%.Example 3. In the same way as in example 1, at the same load of components, the reaction is carried out for 3 hours at a temperature of 22 ° C. The yield of the target product is 97%.
Пример 4. В аналогичных условиях при той же загрузке компонентов примера 1 проводят реакцию в течение 3 часов при температуре 25°С. Выход целевого продукта составляет 99%.Example 4. Under similar conditions, with the same load of the components of example 1, the reaction is carried out for 3 hours at a temperature of 25 ° C. The yield of the target product is 99%.
Пример 5. Испытания на гербицидную активность водорастворимой соли N1,N1,N4,N4-тетраметил-2-бутин-1,4-диамина с N-фосфонометилглицином (1) и изопропиламиновой соли N-фосфонометилглицина (2) в качестве прототипа проводили на паровом поле по схеме «пробит-анализа». Используют серию из не менее 6-8 доз соединений при норме расхода воды 600 л/га. Результаты через 2 недели после обработки показаны в табл. 1.Example 5. Tests for the herbicidal activity of the water-soluble salt of N 1 , N 1 , N 4 , N 4- tetramethyl-2-butyn-1,4-diamine with N-phosphonomethylglycine (1) and the isopropylamine salt of N-phosphonomethylglycine (2) as the prototype was carried out on a steam field according to the "probit analysis" scheme. Use a series of at least 6-8 doses of compounds with a water flow rate of 600 l / ha. The results 2 weeks after treatment are shown in table. one.
Участок парового поля, засоренный преимущественно однолетними сорняками (горчица полевая, ярутка полевая, марь белая, щирица, горец шероховатый, гречишка вьюнковая, ромашка непахучая, мятлик однолетний, щетинник зеленый) высотой 15-20 см, обрабатывают соединением (1) в дозах 0,7 и 1,4 кг ДВ/га. Результаты сравнивают с результатами аналогичной обработки изопропиламиновой солью N-фосфонометилглицина в качестве известного соединения (2). Норма расхода воды 600 л/га, продолжительность опыта 1 месяц (табл. 2).A section of the steam field, predominantly littered with annual weeds (field mustard, field yarrow, white gauze, shiritsa, rugged mountaineer, buckwheat buckwheat, odorless chamomile, annual bluegrass, green bristle) 15-20 cm high, is treated with compound (1) in doses of 0, 7 and 1.4 kg of Far East / ha. The results are compared with the results of a similar treatment with the isopropylamine salt of N-phosphonomethylglycine as the known compound (2). The rate of water consumption is 600 l / ha, the duration of the experiment is 1 month (table. 2).
Участок залежи, заросший преимущественно многолетними сорняками (вьюнок полевой, бодяк полевой, щавель курчавый, осот желтый, пырей ползучий) высотой 20-25 см, опрыскивают растворами тех же самых гербицидов (1) и (2) при нормах расхода 1,4 и 2,8 кг ДВ/га. Продолжительность опыта - 5 недель после обработки. Результаты показаны в табл. 3.The site of the deposit, overgrown mainly by perennial weeds (field bindweed, field thistle, curly sorrel, yellow sow thistle, creeping wheatgrass) with a height of 20-25 cm, is sprayed with solutions of the same herbicides (1) and (2) at flow rates of 1.4 and 2 , 8 kg DV / ha. The duration of the experiment is 5 weeks after treatment. The results are shown in table. 3.
Claims (6)
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| RU2016120787A RU2619948C1 (en) | 2016-05-26 | 2016-05-26 | N1,n1,n4,n4-tetramethyl-2-butyne-1,4-diamine salt with n-phosphonomethylglycine, showing herbicid activity and the method of its production |
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| RU2016120787A RU2619948C1 (en) | 2016-05-26 | 2016-05-26 | N1,n1,n4,n4-tetramethyl-2-butyne-1,4-diamine salt with n-phosphonomethylglycine, showing herbicid activity and the method of its production |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| RU2408572C2 (en) * | 2008-08-05 | 2011-01-10 | Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран | Method of producing n1,n1,n4,n4-tetramethyl-2-butyne-1,4-diamine |
| WO2014095785A1 (en) * | 2012-12-19 | 2014-06-26 | Akzo Nobel Chemicals International B.V. | Compositions and methods for improving the compatibility of water soluble herbicides salts and concentrated fertilizer |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2408572C2 (en) * | 2008-08-05 | 2011-01-10 | Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран | Method of producing n1,n1,n4,n4-tetramethyl-2-butyne-1,4-diamine |
| WO2014095785A1 (en) * | 2012-12-19 | 2014-06-26 | Akzo Nobel Chemicals International B.V. | Compositions and methods for improving the compatibility of water soluble herbicides salts and concentrated fertilizer |
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