SU1042611A3 - Process for preparing derivatives of thiocarbamoyl guanidine - Google Patents

Process for preparing derivatives of thiocarbamoyl guanidine Download PDF

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Publication number
SU1042611A3
SU1042611A3 SU813289248A SU3289248A SU1042611A3 SU 1042611 A3 SU1042611 A3 SU 1042611A3 SU 813289248 A SU813289248 A SU 813289248A SU 3289248 A SU3289248 A SU 3289248A SU 1042611 A3 SU1042611 A3 SU 1042611A3
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Prior art keywords
carbon atoms
general formula
compounds
group
thiocarbamoyl
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SU813289248A
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Russian (ru)
Inventor
Вартон Дерек
Барретт Энтони
Колле Роберто
Гоццо Франко
Прециузо Циро
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Монтэдисон С.П.А. (Фирма)
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Priority claimed from IT23622/79A external-priority patent/IT1162545B/en
Priority claimed from IT23621/79A external-priority patent/IT1121579B/en
Application filed by Монтэдисон С.П.А. (Фирма) filed Critical Монтэдисон С.П.А. (Фирма)
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    • 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
    • C07D295/215—Radicals derived from nitrogen analogues of 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
    • A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/24—Derivatives of thiourea containing any of the groups, X being a hetero atom, Y being any atom
    • C07C335/28—Y being a hetero atom, e.g. thiobiuret
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/30—Isothioureas
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/30—Isothioureas
    • C07C335/32—Isothioureas having sulfur atoms of isothiourea groups bound to acyclic carbon atoms

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  • 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)

Abstract

A method of combatting weeds comprising applying to the soil pre- emergence and/or post-emergence of said weeds at a dosage rate of from 1 to 6 kg/ha one or more herbicide compounds having the general formula <IMAGE> in which: each R represents a phenyl group which may be substituted by one or more substituents selected from halogen atoms, an alkyl group having one to three carbon atoms and a haloalkyl group having 1 to 3 carbon atoms, R<1> and R<2> independently represent an alkyl group having 1 to 3 carbon atoms, and alkoxyl group having 1 to 3 carbon atoms or R<1> and R<2> together form an alkylidenic chain of 4 or 5 carbon atoms which may be interrupted by a heteroatom, and n is 1 or 2. Many of the compounds of formulae (I) and (II) are new. The compounds may be prepared by the following reactions: <IMAGE>

Description

«. Изобретение относитс  к способу полумени  новых производных тиокар бамоилгуанй-цина общей формулы 11-С-Ж-Ж, I t и U.Ь где R - фенил, ч-метилфенил, j-трифторметилфенил , -хлорфенил или З. -Дихлорфенил; R и R метил или вместе образуют алкилиреновую цеп содержащую k-S атомов углерода, и котора  мо жет быть прервана атомом кислорода, которые обладают гербицидиой активностью и могут поэтому найти приме нение в сельском хоз йстве. Известно окисление S-функций в с русодержащих соединени х йодом до получени  соответствующих дисульфидов lj , а также расщепление последних нуклеофильными реагентами 2 Целью изобретени  йвл етс  полумение новых производных тмокарбамоилгуанидина . Поставленна  цель достигаетс  способом получени  производных тио кёрбамоилгуанидина общей формулы t заключающимс  в том, что соединени общей формулы tl S и 3. t где R, R и R.2 - имеют указанные значени , подвергают окислению йодом в среде хлороформа в присутствии триэтиламина с последующей обработкой пол чанного при этом соединени  общей (формулы Ш @« где R, R и R2 имеют указанные зн мени  , трифторуксусной кислотой в среде лороформа и выделением целевого продукта. Выход целевого продукта 33-71 ;. . Процесс провод т при комнатной температуре. Пример 1.А Получение дисульфида N, диМетил- фенилформамидина , 5j2 г йода в 100 мл хлороформа добавл ют по капл м при перемешивании к раствору 5 г. М,М-диметил-М-фенил-тиомочевины и 7,5 мл триэтиламина в 50 мл хлороформа. Добавление продолжают до тех пор, пока окраска йода не остаетс  посто нной в реакционной смеси. Через . 15 мин перемешивание прекращают, реакционную смесь промывают 750 мл воды и сушат безводным сульфатом натри . После удалени  растворител  получают желтое масло, которое кристаллизуют из н-гексана. Получают г ( указанного продукта с т.пл. Зб-бО С. НайденоД: С 60, Н 6,2;N 15,65. C gH2zN4S2; 357,7 ВымисленоД: С 60,3; Н 6,2; , 3 Б. Получение N , N -димети -N ,N -дифенил-N -/(N ,N-димeтил) тиокарбамоилгуанидина . мл трифторуксусной кислоты добавл ют к раствору 2 г дисульфида N, N -диметил-N -фенил-формамидина в 200 мл хлороформа. Реакционную смесь оставл ют сто ть в течение 15 мин при комнатной температуре, после чего ее промывают насыщенным раствором бикарбоната натри  и сушат безводным сульфатом натри . После удалени  растворител  смесь выпаривают в вакууме, остаток кристаллизуют из смеси н-гексана и бензола (70:30).Получают 1,3 г (7U) целевого продукта с т.пл.119-120 0 Найдено,I: С 66,5; Н 6,85; N 17,2; 326, Вычислено,: С 66,2; Н 6,8; N 17,2 Аналогично получают соединени  общей формулы 1, которые сведены в табл.1. Новые соединени  формулы 1 обладают гербицидной активностью. Известны соединени , близкие по структуре к описываемым, например N -(3,-дихлорфенил)-Н,М-диметилмочевина , обладаща  гербицидной активностью .". The invention relates to a method of half-novels of the thiocar bamoylguan-cyn derivatives of the general formula 11-CF · W, I t and U.L where R is phenyl, h-methylphenyl, j-trifluoromethylphenyl, -chlorophenyl or Z.-Dichlorophenyl; R and R methyl or together form an alkyrene chain containing k-S carbon atoms, and which can be interrupted by an oxygen atom, which have herbicidal activity and can therefore be used in agriculture. It is known to oxidize S-functions in compounds containing iodine to obtain the corresponding disulfides lj, as well as cleavage of the latter with nucleophilic reagents 2 The aim of the invention is to complete new derivatives of tmocarbamoylguanidine. The goal is achieved by the method of obtaining the derivatives of thio kerbamoylguanidine of the general formula t consisting in that the compounds of the general formula tl S and 3. t where R, R and R.2 - have the indicated values, are subjected to oxidation with iodine in chloroform medium in the presence of triethylamine followed by treatment The compound obtained in this case (Formula III @ where R, R and R2 have the indicated meanings, with trifluoroacetic acid in the medium of loroform and isolation of the target product. The yield of the desired product is 33-71; .. The process is carried out at room temperature. Example 1 .A Preparation of N disulfide, dimethylphenylformamidine, 5j2 g of iodine in 100 ml of chloroform is added dropwise with stirring to a solution of 5 g of M, M-dimethyl-M-phenyl-thiourea and 7.5 ml of triethylamine in 50 ml of chloroform The addition is continued until the iodine color remains constant in the reaction mixture. After 15 min, stirring is stopped, the reaction mixture is washed with 750 ml of water and dried with anhydrous sodium sulfate. After removing the solvent, a yellow oil is obtained which is crystallized from n-hexane . Get g (of the specified product with so pl. Zb-BO C. Found: C 60, H 6.2; N 15.65. C gH2zN4S2; 357.7 He out of D: C 60.3; H 6.2;, 3 B. Preparation of N, N-dimethyl-N, N-diphenyl-N - / (N, N-dimethyl) thiocarbamoylguanidine. Ml of trifluoroacetic acid is added to a solution of 2 g of N, N-dimethyl-N-phenyl-formamidine disulfide in 200 ml of chloroform. The reaction mixture is left to stand for 15 minutes at room temperature, after which it is washed with a saturated solution of sodium bicarbonate and dried with anhydrous sodium sulfate. After removing the solvent, the mixture is evaporated in a vacuum, the residue they are promoted from a mixture of n-hexane and benzene (70:30). 1.3 g (7U) of the desired product are obtained with mp 119-120 0 Found, I: C, 66.5; H, 6.85; N 17, 2; 326, Calculated: C 66.2; H 6.8; N 17.2 Compounds of general formula 1 are obtained in a similar manner, which are summarized in Table 1. New compounds of formula 1 possess herbicidal activity. described, for example, N- (3, -dichlorophenyl) -H, M-dimethylurea, having herbicidal activity.

Однако гербицидна  активность сопровождаетс  фитотоксичностью.However, herbicidal activity is accompanied by phytotoxicity.

Новые соединени  формулы 1, полученные описанным способом, про вл   гербицидную активность , не обладают фитотоксично ью.The new compounds of formula 1, obtained in the manner described, have shown herbicidal activity, do not possess phytotoxicity.

Пример 2 иллюстрирует биологическую активность новых соединений. Example 2 illustrates the biological activity of new compounds.

.Примё р 2, В горшки высотой 10 см и диаметром 10 см, содержащи песчаную почву, засеивают семена указанных в табл,2 растений и затем добавл ют воду в количестве, необходиMOM дл  хорошего прорастани  и всхода. Example 2, In the pots with a height of 10 cm and a diameter of 10 cm, containing sandy soil, sow the seeds indicated in the table, 2 plants and then add water in an amount necessary for good germination and germination.

,сем н. Горшки дел т на две группы.this family The pots are divided into two groups.

.Первую группу не обрабатывают гербицидом и используют в качестве контрол . Вторую группу обрабатывают через один день после посева водноацетоновой дисперсией (20 об.) гербицида, примен емого в количестве 6 кг/га. Все горшки содержат под наблюдением в теп ице при 15-2 с, относительной влажности 70, световбм периоде 12 ч, интенсивности освеще ни  2500 лк.The first group is not treated with a herbicide and is used as a control. The second group is treated one day after sowing with a water-acetone dispersion (20 vol.) Of the herbicide used in an amount of 6 kg / ha. All pots are kept under observation at a temperature of 15–2 s, relative humidity 70, light of 12 h, intensity of illumination is not 2500 lux.

Каждый второй день все горшки равномерно поливают дл  того,чтобы обеспечить степень влажности, достаточную дл  хорошего роста растений. ЧерезEvery second day, all pots are watered evenly in order to ensure a sufficient degree of moisture for good plant growth. Through

28 дней после обработки осуществл ют контроль дл  оценки вегетативной ctaдии растений. Результаты проверки выражают в соответствии со шкалой от О (рост равен росту контрол )/ до k (полна  остановка роста или полное уничтожение растений).28 days after treatment, controls are performed to evaluate the vegetative stage of the plants. The test results are expressed in accordance with the scale of O (growth equals growth of control) / to k (full stop of growth or complete destruction of plants).

В опытах примен ютс  следующие сорн ки: Однодольные: А Echinochloa crusgal15;The following weeds are used in the experiments: Monocotyledons: And Echinochloa crusgal15;

Б Avena fatua;B Avena fatua;

В « Lol ium J taklcum; Двудольные: Г Stellaria media;In "Lol ium J taklcum; Dicots: G Stellaria media;

Д Ipomea purpurea и следующие полезные растени :D Ipomea purpurea and the following beneficial plants:

Е кукуруза;E corn;

Ж фасоль;F bean;

3 горох;3 peas;

И пшеница;And wheat;

К хлопок;To cotton;

Л со L with

Гербициды, растени  и результаты опытов сведены в табл.2.Herbicides, plants and the results of the experiments are summarized in Table 2.

Как видно из табл.2 новые производные тиокарбамоилгуанидина формулы 1 про вл ют гербицидную активность в отношении многих растений. При этом указанна  активность не сопровождаетс  фитотоксичностью.As can be seen in Table 2, new thiocarbamoylguanidine derivatives of formula 1 exhibit herbicidal activity against many plants. However, this activity is not accompanied by phytotoxicity.

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А N -(3 .-дихлорфенил)-N ,М-диметилмочевина.And N - (3.-Dichlorophenyl) -N, M-dimethylurea.

10 Таблица 210 Table 2

Claims (1)

СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ ТИОКАРБАМОИЛГУАНИДИНА общей формулы 1 где R - фенил, 4-метилфенил,3-трифторметилфенил, 4-хлорфенил или 3,4-дихлорфенил;METHOD FOR PRODUCING THIOCARBAMOYLGUANIDINE DERIVATIVES of the general formula 1 where R is phenyl, 4-methylphenyl, 3 - trifluoromethylphenyl, 4-chlorophenyl or 3,4-dichlorophenyl; R^ и R^ · метил или вместе образуют алкилиденовую цепь, содержащую 4-5 атомов углерода, и которая может быть прервана атомом кислорода, отличающийся тем, что соединение общей формулы ИR ^ and R ^ · methyl or together form an alkylidene chain containing 4-5 carbon atoms, and which can be interrupted by an oxygen atom, characterized in that the compound of General formula And S Ό' и ΛS Ό 'and Λ X где R , R и R2 - имеют указанные значения, . подвергают окислению йодом в среде хлороформа в присутствии триэтиламина с последующей обработкой полученного при этом соединения общей формулы 1« R -η /X where R, R and R 2 - have the indicated meanings,. subjected to oxidation with iodine in chloroform in the presence of triethylamine, followed by treatment of the resulting compound of General formula 1 "R -η / ИNIN Н||H || Сс . ''s-sf У-к, 1ISS '' s-sf Uk, 1 I Λв, где R, R и R - имеют указанные значения, трифторуксусной кислотой в среде хлороформа и выделением целевого продукта.Λв, where R, R and R - have the indicated meanings, with trifluoroacetic acid in chloroform medium and isolation of the target product. SU <и) 1042611 >SU < and) 1042611> 10426 1110426 11
SU813289248A 1979-06-15 1981-05-29 Process for preparing derivatives of thiocarbamoyl guanidine SU1042611A3 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT23622/79A IT1162545B (en) 1979-06-15 1979-06-15 HERBICIDES
IT23621/79A IT1121579B (en) 1979-06-15 1979-06-15 NEW HERBICIDES

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SU1042611A3 true SU1042611A3 (en) 1983-09-15

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SU802934906A SU1005648A3 (en) 1979-06-15 1980-06-16 Method for controlling weed plants
SU813289248A SU1042611A3 (en) 1979-06-15 1981-05-29 Process for preparing derivatives of thiocarbamoyl guanidine

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BR (1) BR8003690A (en)
CA (1) CA1147729A (en)
CH (1) CH652889A5 (en)
DE (1) DE3022057A1 (en)
FR (2) FR2459230B1 (en)
GB (1) GB2057426B (en)
IL (1) IL60315A (en)
SU (2) SU1005648A3 (en)

Families Citing this family (1)

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Publication number Priority date Publication date Assignee Title
DE3101121A1 (en) * 1981-01-15 1982-09-02 Wacker-Chemie GmbH, 8000 München "AROMATICALLY SUBSTITUTED FORMAMIDINO-THIOURANE AS AN HERBICIDE AGENT"

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH340370A (en) * 1955-06-17 1959-08-15 Ciba Geigy Use of salts of formamidine monosulfide and derivatives of formamidine monosulfide or disulfide as pesticides
US3759991A (en) * 1970-05-04 1973-09-18 Exxon Research Engineering Co Thiocarbamylated guanidines - growth regulant

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
1. Вейганд-Хильгетаг. Методы эксперимента в органической химии. М., Хими , 1968, с.609. 2. Сигэру Оаэ. Хими органических соединений, М., Хими , 1975, с.172. *

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IL60315A (en) 1984-12-31
DE3022057A1 (en) 1980-12-18
FR2459230B1 (en) 1986-04-18
FR2459230A1 (en) 1981-01-09
CA1147729A (en) 1983-06-07
GB2057426B (en) 1983-08-10
CH652889A5 (en) 1985-12-13
BR8003690A (en) 1981-01-13
SU1005648A3 (en) 1983-03-15
IL60315A0 (en) 1980-09-16
FR2464946B1 (en) 1983-03-18
FR2464946A1 (en) 1981-03-20
GB2057426A (en) 1981-04-01

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