RU2626648C1 - Salt n1, n1, n4, n4-tetramethyl-2-butyne-1,4-diamine with n-phosphonomethyl glycin, through herbicid activity and method of its production - Google Patents

Salt n1, n1, n4, n4-tetramethyl-2-butyne-1,4-diamine with n-phosphonomethyl glycin, through herbicid activity and method of its production Download PDF

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RU2626648C1
RU2626648C1 RU2016120778A RU2016120778A RU2626648C1 RU 2626648 C1 RU2626648 C1 RU 2626648C1 RU 2016120778 A RU2016120778 A RU 2016120778A RU 2016120778 A RU2016120778 A RU 2016120778A RU 2626648 C1 RU2626648 C1 RU 2626648C1
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diamine
tetramethyl
salt
methoxy
butyn
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Владимир Михайлович Крутьков
Борис Иванович Вороненко
Равил Исмагилович Хуснутдинов
Асхат Габдрахманович Ибрагимов
Наталия Наильевна Махмудиярова
Ильмира Мухаррамовна Ганиева
Александр Михайлович Колбин
Усеин Меметович Джемилев
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Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук
Государственное бюджетное учреждение Республики Башкортостан "Научно-исследовательский технологический институт гербицидов и регуляторов роста растений с опытно-экспериментальным производством Академии наук Республики Башкортостан"
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    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
    • 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
    • A01N37/36—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 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—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 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—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 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/62—Quaternary ammonium compounds
    • C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups

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Abstract

FIELD: chemistry.
SUBSTANCE: invention relates to a novel salt of N1,N1,N4,N4-tetramethyl-2-butyn-1,4-diamine with 2-methoxy-3,6-dichlorobenzoate of the corresponding structural formula (1). The compound shows high herbicidal activity, especially when combating annual and perennial dicotyledonous weeds, and can find application in agriculture. The salt corresponds to the structural formula
Figure 00000011
. The invention also relates to a process of preparation of a salt of a compound (1). The method is that the N1,N1,N4,N4-tetramethyl-2-butyn-1,4-diamine with an equimolar amount of an aqueous solution of 2-methoxy-3,6-dichlorobenzoic acid at atmospheric pressure, preferably at a temperature of 20-25°C with stirring for 2.5-3.0 hours. The yield of the product is 85-99%.
EFFECT: new compound is superior in functional activity to a known compound with high selectivity and is effective in controlling weeds in wheat crops.
4 cl, 2 tbl 5 ex

Description

Предлагаемая группа изобретений относится к новым химическим соединениям с биологической активностью, конкретно к соли 2-метокси-3,6-дихлоробензоата N1,N1,N4,N4-тетраметил-2-бутин-1,4-диамина формулы (1) в качестве гербицида для борьбы с однолетними и многолетними двудольными сорняками в сельском хозяйстве, и способу ее получения.The proposed group of inventions relates to new chemical compounds with biological activity, in particular to the salt of 2-methoxy-3,6-dichlorobenzoate N 1 , N 1 , N 4 , N 4 -tetramethyl-2-butyn-1,4-diamine of the formula (1 ) as a herbicide for the control of annual and perennial dicotyledonous weeds in agriculture, and the method for its production.

Figure 00000001
Figure 00000001

Известна соль 2-метокси-3,6-дихлоробензоата диметиламина (2), проявляющая гербицидную активность (Мельников Н.Н., Новожилов К.В., Белан С.Р. Справочник. Пестициды и регуляторы роста растений, М.: Химия, 1995, с. 66).Known salt of 2-methoxy-3,6-dichlorobenzoate dimethylamine (2), showing herbicidal activity (Melnikov N.N., Novozhilov K.V., Belan S.R. Directory. Pesticides and plant growth regulators, M .: Chemistry, 1995, p. 66).

Задачей предлагаемого изобретения является создание в ряду производных 2-метокси-3,6-дихлоробензойной кислоты 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 in a series of derivatives of 2-methoxy-3,6-dichlorobenzoic acid of a new alkynamine salt having improved herbicidal properties in relation to annual and perennial dicotyledonous weeds, which can be used in agriculture.

Результат достигается тем, что в качестве водорастворимого соединения, обладающего гербицидной активностью, создана соль 2-метокси-3,6-дихлоробензоата N1,N1,N4,N4-тетраметил-2-бутин-1,4-диамина формулы (1).The result is achieved in that as a water-soluble compound having herbicidal activity, a salt of 2-methoxy-3,6-dichlorobenzoate N 1 , N 1 , N 4 , N 4 -tetramethyl-2-butyn-1,4-diamine of the formula ( one).

Способ получения соли 2-метокси-3,6-дихлоробензоата N1,N1,N4,N4-тетраметил-2-бутин-1,4-диамина 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. 10.01.11. Бюл. №1) с эквимольным количеством водного раствора 2-метокси-3,6-дихлоробензойной кислоты при атмосферном давлении и предпочтительно при температуре 20-25°С в течение 2,5-3,0 часов. Выделяют водорастворимую соль 2-метокси-3,6-дихлоробензоата N1,N1,N4,N4-тетраметил-2-бутин-1,4-диамина формулы (1) с выходом 85-99%. Реакция протекает по схеме:The method for producing the salt of 2-methoxy-3,6-dichlorobenzoate N 1 , N 1 , N 4 , N 4- tetramethyl-2-butyn-1,4-diamine is based on the mixing of N 1 , N 1 , N 4 , N 4 - tetramethyl-2-butyn-1,4-diamine (Dzhemilev U.M., Shaybakova M.G., Makhmudiyarov G.A., Ibragimov A.G., Titova I.G. Method for the preparation of N 1 , N 1 , N 4 , N 4- tetramethyl-2-butyn-1,4-diamine. Patent of the Russian Federation No. 2408572, publ. 10.01.11. Bull. No. 1) with an equimolar amount of an aqueous solution of 2-methoxy-3,6-dichlorobenzoic acid at atmospheric pressure and preferably at a temperature of 20-25 ° C for 2.5-3.0 hours. The water-soluble salt of 2-methoxy-3,6-dichlorobenzoate N 1 , N 1 , N 4 , N 4- tetramethyl-2-butyn-1,4-diamine of the formula (1) is isolated in 85-99% yield. The reaction proceeds according to the scheme:

Figure 00000002
Figure 00000002

Figure 00000003
Figure 00000003

Спектральные характеристики соли 2-метокси-3,6-дихлоробензоата N1,N1,N4,N4-тетраметил-2-бутин-1,4-диамина формулы (1):The spectral characteristics of the salt of 2-methoxy-3,6-dichlorobenzoate N 1 , N 1 , N 4 , N 4- tetramethyl-2-butyn-1,4-diamine of the formula (1) :

Figure 00000004
Figure 00000004

Спектр ЯМР 13С (D2O, м.д.): 42.68 ((А), С1,8,9,10); 46.98 ((А), С3,6); 61.86 ((Б), С7); 79.50 ((А), С4,5); 125.58 ((Б), С5); 126.34 ((Б), С1); 128.19 ((Б), С3); 129.09 ((Б), С6); 136.27 ((Б), С4); 152.34 ((Б), С2); 169.68 ((Б), С8). ИК, см-1: 643 (С-Н); 719 (С-Cl); 814 (С-Н); 1007 (С-ОН); 1039 (O-СН3); 1163 (C-N); 1235 (O-СН3); 1455 (C-N); 1580 (Ar); 1613 (С=O); 2823-2939 (С-Н); 3418 (О-Н). 13 C NMR spectrum (D 2 O, ppm): 42.68 ((A), C 1,8,9,10 ); 46.98 ((A), C 3.6 ); 61.86 ((B), C 7 ); 79.50 ((A), C 4.5 ); 125.58 ((B), C 5 ); 126.34 ((B), C 1 ); 128.19 ((B), C 3 ); 129.09 ((B), C 6 ); 136.27 ((B), C 4 ); 152.34 ((B), C 2 ); 169.68 ((B), C 8 ). IR, cm -1 : 643 (C-H); 719 (C-Cl); 814 (C-H); 1007 (C-OH); 1039 (O-CH 3 ); 1163 (CN); 1235 (O-CH 3 ); 1455 (CN); 1580 (Ar); 1613 (C = O); 2823-2939 (C-H); 3418 (OH).

Вычислено, %: С 53.19, Н 6.14, N 7.75, О 13.29, Сl 19.63. Найдено, %: С 52.95, Н 5.54, N 6.10. C16H22N2Cl2O3.Calculated,%: С 53.19, Н 6.14, N 7.75, О 13.29, Сl 19.63. Found,%: C 52.95, H 5.54, N 6.10. C 16 H 22 N 2 Cl 2 O 3 .

Спектральные характеристики 2-метокси-3,6-дихлоробензоата:Spectral characteristics of 2-methoxy-3,6-dichlorobenzoate:

Figure 00000005
Figure 00000005

Спектр ЯМР 13С (DMSO, м.д.): 62.41 ((Б), С7); 126.57 ((Б), С5); 128.49 ((Б), С1); 131.92 ((Б), С3); 132.01 ((Б), С6); 133.04 ((Б), С4); 152.97 ((Б), С2); 165.59 ((Б), С8). 13 C NMR spectrum (DMSO, ppm): 62.41 ((B), C 7 ); 126.57 ((B), C 5 ); 128.49 ((B), C 1 ); 131.92 ((B), C 3 ); 132.01 ((B), C 6 ); 133.04 ((B), C 4 ); 152.97 ((B), C 2 ); 165.59 ((B), C 8 ).

Спектральные характеристики N1,N1,N4,N4-тетраметил-2-бутин-1,4-диамина формулы (1):Spectral characteristics of N 1 , N 1 , N 4 , N 4- tetramethyl-2-butyn-1,4-diamine of the formula (1) :

Figure 00000006
Figure 00000006

Пример 1. В колбу с водным раствором, содержащим 221 г 3,6-дихлор-2-пиридинкарбоновой кислоты, загружают 116 г порошка N1N1N1N4-тетра-метил-2-бутин-1,4-диамина. Смесь перемешивают в течение 2,5 часов при атмосферном давлении и температуре 23,5°С, после чего определяют выход целевого продукта. Он составляет 85%. Затем осуществляют выпаривание водного раствора при температуре 35°С до получения постоянного веса.Example 1. Into a flask with an aqueous solution containing 221 g of 3,6-dichloro-2-pyridinecarboxylic acid, 116 g of N 1 N 1 N 1 N 4- tetra-methyl-2-butyn-1,4-diamine powder were charged. The mixture is stirred for 2.5 hours at atmospheric pressure and a temperature of 23.5 ° C, after which the yield of the target product is determined. It is 85%. Then carry out the evaporation of an aqueous solution at a temperature of 35 ° C to obtain a constant weight.

Пример 2. Аналогичным образом по примеру 1, при тех же условиях смесь перемешивают в течение 3 часов, после чего определяют выход целевого продукта. Он составляет 97%. Затем осуществляют выпаривание водного раствора при температуре 30°С до получения постоянного веса.Example 2. In the same manner as in example 1, under the same conditions, the mixture is stirred for 3 hours, after which the yield of the target product is determined. He is 97%. Then carry out the evaporation of the aqueous solution at a temperature of 30 ° C to obtain a constant weight.

Пример 3. Аналогичным образом по примеру 1, при той же загрузке компонентов проводят реакцию в течение 3 часов при температуре 20°С. Выход целевого продукта составляет 92%. Затем осуществляют выпаривание водного раствора при температуре 33°С до получения постоянного веса.Example 3. In the same way as in example 1, at the same loading of the components, the reaction is carried out for 3 hours at a temperature of 20 ° C. The yield of the target product is 92%. Then carry out the evaporation of the aqueous solution at a temperature of 33 ° C to obtain a constant weight.

Пример 4. При аналогичных условиях примера 3 проводят реакцию при температуре 25°С. Определяют выход целевого продукта. Он составляет 99%. Затем осуществляют выпаривание водного раствора при температуре 30°С до получения постоянного веса.Example 4. Under similar conditions of example 3, the reaction is carried out at a temperature of 25 ° C. The yield of the target product is determined. He is 99%. Then carry out the evaporation of the aqueous solution at a temperature of 30 ° C to obtain a constant weight.

Пример 5. Испытания соли 2-метокси-3,6-дихлоробензоата N1,N1,N4,N4-тетраметил-2-бутин-1,4-диамина (1) проводили в полевом эксперименте на посевах пшеницы по схеме «пробит-анализа», используя 7 доз действующего вещества. Площадь делянки 10 м2, повторность по каждой дозе 4-кратная. Расход воды при опрыскивании 600 л/га, продолжительность опытов после обработки 2 недели. Эталоном служила соль 2-метокси-3,6-дихлоробензоата диметиламина (2). Эффективность соединений оценивали по ингибированию роста растений, выраженному в процентах от необработанного контроля. Все численные процедуры выполнялись в расчете на одно растение, а по совокупности данных определяли показатель ЕД50. Результаты приведены в табл. 1.Example 5. Tests of the salt of 2-methoxy-3,6-dichlorobenzoate N 1 , N 1 , N 4 , N 4- tetramethyl-2-butyn-1,4-diamine (1) were carried out in a field experiment on wheat crops according to the scheme " probit analysis "using 7 doses of the active substance. The plot area is 10 m 2 , the repetition for each dose is 4-fold. The consumption of water during spraying is 600 l / ha, the duration of the experiments after treatment is 2 weeks. The dimethylamine salt of 2-methoxy-3,6-dichlorobenzoate (2) served as a reference. The effectiveness of the compounds was evaluated by inhibition of plant growth, expressed as a percentage of the untreated control. All numerical procedures were performed per one plant, and the ED 50 indicator was determined from the totality of the data. The results are shown in table. one.

Figure 00000007
Figure 00000007

Избирательность действия 2-метокси-3,6-дихлоробензоата N1,N1,N4,N4-тетраметил-2-бутин-1,4-диамина определяют в опыте с обработкой посевов пшеницы сорта «Экадо» гербицидом при норме расхода 0,4 кг/га. Урожайные данные опытов приведены в табл. 2.The selectivity of the action of 2-methoxy-3,6-dichlorobenzoate N 1 , N 1 , N 4 , N 4- tetramethyl-2-butyn-1,4-diamine is determined in an experiment with the processing of crops of wheat variety "Ekado" herbicide at a flow rate of 0 4 kg / ha. Yield data of the experiments are given in table. 2.

Figure 00000008
Figure 00000008

НСР0.95=13,1%NDS 0.95 = 13.1%

Claims (5)

1. Соль N1,N1,N4,N4-тетраметил-2-бутин-1,4-диамина с 2-метокси-3,6-дихлоробензоатом структурной формулы1. Salt N 1 , N 1 , N 4 , N 4- tetramethyl-2-butyn-1,4-diamine with 2-methoxy-3,6-dichlorobenzoate of the structural formula
Figure 00000009
Figure 00000009
 2. Соль по п. 1, которая проявляет гербицидную активность.2. The salt according to claim 1, which exhibits herbicidal activity. 3. Соль по п. 1, которая проявляет гербицидную активность в отношении однолетних и многолетних двудольных сорняков.3. Salt according to claim 1, which exhibits herbicidal activity against annual and perennial dicotyledonous weeds. 4. Способ получения соли N1,N1,N4,N4-тетраметил-2-бутин-1,4-диамина с 2-метокси-3,6-дихлоробензоатом структурной формулы по п. 1, включающий взаимодействие N1,N1,N4,N4-тетраметил-2-бутин-1,4-диамина с эквимольным количеством водного раствора 2-метокси-3,6-дихлоробензойной кислоты при атмосферном давлении и предпочтительно при температуре 20-25°С и перемешивании в течение 2,5-3,0 часов.4. The method of producing salts of N 1 , N 1 , N 4 , N 4- tetramethyl-2-butyn-1,4-diamine with 2-methoxy-3,6-dichlorobenzoate of the structural formula according to claim 1, comprising the interaction of N 1 , N 1 , N 4 , N 4- tetramethyl-2-butyn-1,4-diamine with an equimolar amount of an aqueous solution of 2-methoxy-3,6-dichlorobenzoic acid at atmospheric pressure and preferably at a temperature of 20-25 ° C with stirring within 2.5-3.0 hours.
RU2016120778A 2016-05-26 2016-05-26 Salt n1, n1, n4, n4-tetramethyl-2-butyne-1,4-diamine with n-phosphonomethyl glycin, through herbicid activity and method of its production RU2626648C1 (en)

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Citations (4)

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SU1681808A1 (en) * 1989-03-13 1991-10-07 Всесоюзный научно-исследовательский технологический институт гербицидов и регуляторов роста растений Herbicidal composition
RU2461194C1 (en) * 2011-06-16 2012-09-20 Государственное бюджетное учреждение Республики Башкортостан "Научно-исследовательский технологический институт гербицидов и регуляторов роста растений с опытно-экспериментальным производством Академии наук Республики Башкортостан" Herbicidal water-soluble concentrate
RU2482676C1 (en) * 2011-11-21 2013-05-27 Раиль Бакирович Валитов Biologically active compounds having surface-active properties
EA021405B1 (en) * 2009-09-30 2015-06-30 Басф Се Low volatile amine salts of anionic pesticides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1681808A1 (en) * 1989-03-13 1991-10-07 Всесоюзный научно-исследовательский технологический институт гербицидов и регуляторов роста растений Herbicidal composition
EA021405B1 (en) * 2009-09-30 2015-06-30 Басф Се Low volatile amine salts of anionic pesticides
RU2461194C1 (en) * 2011-06-16 2012-09-20 Государственное бюджетное учреждение Республики Башкортостан "Научно-исследовательский технологический институт гербицидов и регуляторов роста растений с опытно-экспериментальным производством Академии наук Республики Башкортостан" Herbicidal water-soluble concentrate
RU2482676C1 (en) * 2011-11-21 2013-05-27 Раиль Бакирович Валитов Biologically active compounds having surface-active properties

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