前苏联专利SU1105115A3 Method of obtaining diphenyl ether derivatives

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专利摘要:
THE WAY OF OBTAINING DERIVATIVE DIPHENYL ETHER ETHER OF A GENERAL FORMULA where A and B are halogen, halogen-substituted lower, al kil, type-0 - 3, with m + n 0-3; is hydrogen, lower C -C alkyl, cyclohexyl or phenyl, characterized in that the compounds of general formula II JL are reacted with alkyl hydrazine of general formula 111 G-d. (L RiNHNC Кз where X is a halogen atom, a nitro group or a phenoxy group of the formula (A) t.: L (B) l. Where A, B, t, n, K, -Ks have the specified values.
公开号:SU1105115A3
申请号:SU813344197
申请日:1981-10-08
公开日:1984-07-23
发明作者:Есимото Такео；Хосоно Акира；Мики Ех；Ода Кенго；Ура Масааки；Сато Ноаки；Тояма Терухико；Татибана Хадзиме；Еномото Юдзи；Фунакоси Ясунобу；Фудзита Такаси；Ходзо Есиката
申请人:Мицуи Тоацу Кемикалз Инкорпорейтед (Фирма)；
IPC主号:

专利说明:

The invention relates to r, uOf: oCv for preparing FioBbix derivatives lif (:; ethol; 1g total ether - l; yl1
, .Nг; I-n
(A); u, f, ..
J xy-o-f VNO, (B) ,, - - / where A and B are halogen, halogen Metz P; 1 nm 511) 1-g m and n are integers 0-1; by lyric
w + n 0-3;
R.-I, is hydrogen, lower Ci-alkyl-5 cyclohexyl-phenyl-lu, which can be used as selective herbicides, cloudy Pbicoic herbicidal activity) ocTii-specific efficacy, It is known that some compounds: with the diphenyl ether, possess the highest germ, their secondary germicinogram, it is known, that its compound contains: For example, e 3 ,, 1 rb-trichloro-4-nitrodiphenyl ether and 2, A-dichloro-3-methoxy-4-nitrodiphenyl ether, are widely used as herbicides for the treatment of rice fields in the period Mj
However, since these connectors have insufficient efficiencies and are inconvenient in that, they cannot completely crush gossorns if time is n; lsgolzopani vnyyueHC; then it is desirable 1: a5p should be treated with herbicides for gagoli naddr- (possessing more viable ones) bicycles). activity and more safety; s.;: LS
FROM more than BeC Fib ;;; r-ne,: And; (
diphenylose ether to i-ihieuschie such gsrbitsidnuyu AKZMvpostt; that could be; settling and dying in many years of weeds in paddy fields.
There is a known method for producing hydrazine by inter, her, and halide corresponding to
Derived BENZO1 OH .- .; with
hydrazine derivatives of the formula:
.tXp 1-de Rj - alkyl i.ggy aralkyl n
radical;
Rn is alkyl; ari: imly; aralkyl radical: i-: Share with the invention} {and - development on (HMione iznastiolS method method
HOJ ;; - PHYSICAL INFORMATION IiOJJblX H 13CM 3 IN ONE DIFFERENTIAL SPACE: (1 oipHt- a,
By placing the fir, the spruce is achieved by the corjiacjio method, in which the compounds of the formula
X (Aim. ((N)
f: voh / VHC
(AT).,./
Y
(BUT)
im.
(AT)
,but
R ,. (iTi) kz
11pre, (we put 1; e compounds of diffg.nilovo) 41 Hpocioio ether vl.chuts; g, Ch111imi for fight against weeds on reed prawns}; ol x. They can be used to; to: for treatment for water nonay, add11, for weed nt-ing, and for treating all: time of the growth period of Ge; J7araem-le co: el. Im pro are erbitsil {th activity on from: io leHiiio -: gel-backlight umbrella, 1G1 (ki m J SciLipHR j w G: O id S and eoccharis kuroguwai, belonging to Petushi millet, which came with a very bad weed on rice 1 mole. with respect to common and to uzkolistvenpoy sgreloiiiicTy trehlistomu belonging h isniaLaeeae L1 family with respect to k: oocnria vaginal is ,, RoLala indica, Inid / igia prostrata and Eciipta prosi: rat: a, which are annuals (iirokolistvenn; 1 and weeds. Kami, etc .. 5 In addition, it is one of the tennines, 1, they have a high selectivity in that their (very toxic to peg) water that is not watery rice is very small.
. a le e. s oe d i n e: o b p i e and forms m L1,} 1 have nai-iHoro the best characteristics in that they show the best herbicidal activity and residual efficacy in tillage before the appearance of weeds , as well as in the processing of stems and leaves, in the fight against weeds, which are difficult to destroy on baseless floors, such as rosychka shelter, foxtail, millet chicken, wheat grass, canary herb Karolinsky, sorghum alepskoe bermudsk grass, pig, Ivan -chay marry bela, pepper mountaineer, limnoharis, ipome, duroshnik, rumeks, mustard field, pass mascara bag etc and do not have phytotoxicity with respect to soybeans and peanuts and cotton, wheat, and, in addition, they have only minor phytotoxicity even when used in high concentrations. Example 1. Preparation of 2-chloro-4-trifluoromethyl-3-hydrazino-4-nitrodiphenyl ether (Compound No. 19, Table 1). 2-Chloro-4-trifluoromethyl-3,4-dinitrodiphenyl ether (7.2 g) and dioxane (50 ml) are placed in a 100 ml four-necked flask, and after dissolution is added dropwise at 5-10 ° G hydrazine hydrate (2 g), then the mixture is stirred at 25–30 ° C for 2 hours. After the reaction has ended, the reaction liquid is poured into 200 ml of water and the resulting precipitated crystals are collected by filtration, washed with water and dried. The crystals thus obtained are recrystallized from ethanol to obtain 5 g of the expected product, having a melting point of 131.5-132 ° C. Example 2. Preparation of 2,4-dichloro-3-hydrazin-4-nitrodiphenyl ether (Compound No. 7, Table 1). 2,4-Bis- (2,4-dichlorophenoxy) nitrobenzene (44.5 g) and dioxane (100 ml) are placed in a 200 ml four-neck flask and, after dissolving, 15 ml of hydrazine hydrate are added, after which the mixture is stirred at 60-80 ° C in for 8 hours. After the completion of the reaction, the obtained liquid is poured into water, and the resulting precipitated crystals are collected by filtration, washed with thermode and dried. The crystals obtained by such a Right are recrystallized from ethanol; 26 g of the expected product is obtained, having a melting point of 124-125 ° C. Example 3. Preparation of 2-chloro-4-trifluoromethyl-3 - (2-H-butylhydrazine) -4-nitrodiphenyl ether (compound No. 21, Table 1) and 2-chloro-4-trifluoromethyl-3 - (1- N-butyl hydrazine) -4-nitrodiphenyl ether (Compound No. 98, Table 1), 2-Chloro-4-trifluoromethyl-3,4-dinitrodiphenyl ether (3.6 g) and dioxane (30 ml) are placed in A 50 ml four-necked flask and, after dissolving, H-butylhydrazine (2 g) is added dropwise, after which the mixture is stirred at room temperature for 2 hours while the resulting reaction liquid is added with 200 ml of benzene, and then the mixture washed with water and dried over anhydrous sodium sulfate. After distilling off the benzene under reduced pressure, the silica gel is purified and separated using a silica gel column using benzene as a developing solvent. 2-chloro-4-trifluoromethyl-3- (2-H-butylhydrazine) is obtained in the form of liquids. -4-nitrodiphenyl ether (1.2 g) and 2-chloro-4-trifluoromethyl-2 - (1-H-butylhydrazine) -4-nitrodiphenyl ether (1.3 g). Example 4. Preparation of 2-chloro-4-trifluoromvtil-3- (2,2-dimesh1Hydrazin) -4-nitrodiphenyl ether (compound No. 23, Table 1). 2-chloro-4-trifluoromethyl-3,4-dinitrodiphenyl ether (7.2 g) and dioxane (100 ml) were placed in a 200 ml four-neck flask and, after dissolving, 1,1-dimethyl hydrazine (2.7 g) was added at room temperature, after which the mixture is moved at 5060 ° C for 5 hours. The resulting reaction liquid is cooled and then poured into water, after which it is extracted with benzene and dried with anhydrous sodium sulfate. After the benzene is removed under reduced pressure, it is cleaned with a silica gel column using benzene as a developing solvent, and 7.7 g of the expected product are obtained in the form of a liquid. Example 5. Preparation of 2-chloro-4-trifluoromethyl-3- (1-methylhydroain 4-nitrodiphenyl ether (compound No. 76, Table 1).
2-Chloro-4-trifluoromethyl-3, 4-dinite rhodi (}) e. Ether (36 g) and dioxane (320 ml) are placed in a 500 ml four-necked flask and dropwise at or at a lower temperature methyl hydrazine (9 g), after which the mixture is stirred at room temperature for 2 hours. The resulting reaction liquid was poured into water and extracted with benzene, then washed with water and dried with anhydrous sodium sulfate. The benzene is distilled off under reduced pressure and recrystallized from ethanol, 24 g of the expected product, having a melting point of 9697 ° C.
Other compounds of the present invention, indicated by the general formula I, and their physical properties are given in Table 1,
Test Example 1.
Testing the ability to suppress weeds on non-soil fields during tillage before germination.
The air-dried soil (10k non-bulk floor (passed through a 14-mesh sieve) is placed in a pot made of resin (a / 1000) and fertilizer compounds are applied to the entire soil layer (N, 2 each 1 g after which the water content in The soil is brought up to 60% of the maximum water retention capacity. The soil is sown with a certain number of seeds of the studied plants or weeds and covered with soil. The liquid is obtained by diluting with water a certain amount of the emulsion obtained from the test compound according to the example preyarata 3, and prykivayut soil with low head via spraying in amounts sootvetstvunltsem flow rate of 10 liters per are.
The treated pot is placed in a greenhouse and provides a supply of water for growing the plant. Thirty days after spraying with the substance, the germination or growth condition of the weeds and cultivated plants is examined to obtain the results given in Table. 2
In tab. Grade 2 phytotoxicity for cultivated plants and herbicidal effects on weeds are expressed according to standard estimates below when comparing the germination or growth condition of weeds or cultivated plants by the dry weight of weeds or cultivated plants in the untreated part.
The compounds tested are characterized by the compound number in Table. 1 (this applies to the following test examples). Among the compounds tested table. 2, compounds 177, 186 can completely suppress the following) weeds with the amount of substance used (10 g of the substance, and the rest can suppress with the amount of the substance used 5 g / ap: foxtail, wheatgrass, canary Caroline, sorghum alepskoe, Bermuda grass, porpoise, pepper mountaineer, limnoharis, ipome, cocklebur, rumex, field mustard, shepherd's purse, etc. Standard estimates. The percentage of weeds or crops that survived, determined by the dry weight of weeds or crops in untreated parts,%:
076-100
151-75
236-50
311-35
46-10
50-5
Test Example 2.
Herbicidal trials in the treatment of stems and leaves of non-prime crops.
The air-dried soil (450 g of a non-filled floor (passed through a 14 mesh sieve) is placed in a pot made of resin (a / 10,000), and a fertilizer compound (N, 2 each 100 mg) is applied to the entire soil layer, after which The soil water content is adjusted to 60% of the maximum water retention capacity. The soil is sown with a certain amount of seeds of the studied plants and evenly covered with soil. The prepared pot is placed in a glass-covered greenhouse and when the plant under study is in a 2-3 leaf growth period, the wire t handled stems and leaves, using a wettable powder prepared according to the above specified example of preparation 3 so that cf. contains the reagent under study and an amount of 1000, 2000 or 5000 ppm. Thirty days after treatment, the growth state of the studied plants is studied so that to obtain the results listed in Table 3. Compound 179 indicated in Table 3 can completely suppress the following weeds with the amount of 5 g / ap used, and other compounds can suppress the weeds with the amount of 2 g / ap used: foxtail , Caroline canary grass, sorghum johnsongrass, Bermuda grass, Bermuda grass, knotweed pepper, Lim noharis, morningglory, cocklebur, Rumex, wild mustard, shepherd's purse, etc. Test example 3. Herbicidal tests for rice fields in the initial period. The soil of a rice field (3.3 kg), in which the seeds of ordinary rice weeds are present (passed through a 14 mesh sieve) is placed in a Wagner pot (a / 5000) and a fertilizer compound (N, P, K20, each 0, 8 g) is applied to the entire soil layer, after which the required amount of water is added and mixed to obtain a state filled with water. The seeds are sown with rice weed seeds and arrowheads of three leaves and Eleocharis Kuroguwai, and two planted seedlings are planted, each of which consists of two young water rice plants (the age of a young plant leaf is 3.0 and then the pot is placed for greenhouse. In the initial period of sprouting of the nods, two days after transplanting the sprouts of water rice, they are treated in a filled state using granules obtained from a specific amount of the test compound according to the example of arata 5. One month after the treatment, the weed germination state and the degree of phytotoxicity for water rice plants are examined, obtaining the results given in Table 4. In Table 4, the assessments showing the weed germination state are divided into 6 stages , as in Test Example 1, and the estimates showing the degree of Litotoxicity for water rice plants are divided into 6 stages of serious harm, great harm, moderate harm, minor harm, minor harm, and harmless. In addition, during the test period, the depth of the water filled pot is maintained at 3 cm using a water leakage system of 1 cm / day. The compounds listed in Table. 4 can suppress Eleocharis Kuroguwai and three-leafed arrowhead when the amount of reagent used is 15 g / ap or can control them when the amount of reagent used is 7 g / ar. Standard phytotoxicity ratings. The percentage of surviving cultivated plants, determined in relation to the dry weight of cultivated plants in the untreated part,%: Serious harm. 0-10 Great harm 11-20 Medium harm 21-50 Minor harm51-90 Minor harm 81-95 Harmless96-100 Example test 4. Initial herbicide test for flood floor (2). The soil (3.3 kg) of the flood ggol, in which the usual seeds of rice weed are usually present (sifted through a 14-mesh sieve) is placed in a Wagner pot (a / 5000) and a udbring compound (N, and KgO, each 0). , 8 g) is applied to the entire soil layer, after which water is added and mixed until a water-saturated state is obtained. The soil is sown with rice weed seeds and three-leaved arrowheads and Eleocharis Kuroguwai and planted two pre-grown seedlings, each of which consists of two young water rice plants (young plant leaf age 3.0) and placed in a greenhouse. In the initial period of weed sprouting, seven days after transplanting water rice plants, they are treated in a water filled state, using granules obtained from a certain amount of the test compounds according to the example of preparation 1. After a month after treatment, the weed sprouting condition and degree phytotoxicity on water rice plants, having obtained the results indicated in Table. 5. In table. 5 assessments, meaning weed germination condition, are divided into 6 stages, as in Test Example 1, and assessments meaning phytotoxicity for water rice plants, are divided into 6 stages, serious harm, great harm, moderate harm, little damage, minor harm and harmless. The evaluation standards are the same as in example 3. In addition, during the test period, the water depth of the pot is maintained at 3 cm using a 1 cm / day water leak system. The compounds tested are listed in table. 5 can suppress arrowhead trefost and Eleocharis Kuroguwai with a quantity of reagent of 15 g / ap.
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98 Commercial product UnprocessedNumber p; 1sn part of Teny Dry veg 22.5 31.8 pncTPinrii
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1105115
26 Continued table. ft 38
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权利要求:
Claims (1)
[1]
METHOD OF PRODUCING DERIVATIVES diphenyl ether of the general formula wherein A and B are - halogen, halogenated lower alkyl, ^- m and η - 0 - 3, and m + η = 0-3;
R ₄ -Rj is hydrogen, LOWEST C4C4-alkyl, cyclohexyl or phenyl, characterized in that the compounds of general formula II are reacted with alkylhydrazine of the general formula III
R, NHN ^
C3 where X is a halogen atom, a nitro group or a phenoxy group of the formula where A, B, tn, n, R ₍ ^_f 3 have the indicated meanings.

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同族专利:

公开号 | 公开日

AU525427B2|1982-11-04|

FR2440943A1|1980-06-06|

DE2944783A1|1980-05-22|

ES485821A1|1980-09-01|

BR7907251A|1980-08-05|

RO84318B|1984-07-30|

US4515628A|1985-05-07|

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AU5259279A|1980-05-15|

RO84391A|1984-08-17|

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FR2440943B1|1981-11-27|

IN151843B|1983-08-13|

MX7633E|1990-04-23|

GB2038319A|1980-07-23|

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GB2038319B|1983-05-05|

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引用文献:

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JP5069023B2|2002-06-18|2012-11-07|旭化成ファーマ株式会社|Calibration material for glycated protein measurement and standard measurement method|JPS5564557A|1978-11-08|1980-05-15|Mitsui Toatsu Chem Inc|Diphenyl ether compound and herbicide containing the same|

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GB8520774D0|1985-08-20|1985-09-25|Shell Int Research|Diphenyl ether herbicides|

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EP0641316B1|1991-11-22|1997-01-22|UNIROYAL CHEMICAL COMPANY, Inc.|Insecticidal phenylhydrazine derivatives|

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US5543404A|1995-07-05|1996-08-06|Uniroyal Chemical Company, Inc|Pesticidal phenylhydrazinephosphates|

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法律状态:

优先权:

申请号 | 申请日 | 专利标题

JP13676978A|JPS5564557A|1978-11-08|1978-11-08|Diphenyl ether compound and herbicide containing the same|

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