Method of preparing amidoxime derivatives

专利摘要:
Amidoxime derivs. of formula Ar-C(NH2)NOCHRCOOR1 (I) are new (where R = H, 1-4C alkyl or phenyl; R1 = H, 1-4C alkyl, or a metal atom; Ar = phenyl substd. by 1-3 of halogens, alkyl, OH, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, CF3 CF3O,CF3S, carboxy, alkoxycarbonyl, NO2 NH2, alkylamino, dialkylamino, acylamino, alkoxycarbonylamino, azido, alkanoyl, sulphamoyl which may be substd. on the N by 1 or 2 alkyl groups or phenyl, or Ar = 5 membered aromatic heterocycle contg. O,N or S opt. substd. by halogen, alkyl, alkoxy, alkylthio or phenyl alkyl; the alkyl, alkoxy, and acyl groups contain up to 4C atoms). At concn. of 1-100g (I)/hl of water, the cpds. have phytohormonal activity and aid fruiting of certain plants, prevent leaf and fruit drop, and increase root formation, At application rates of 0.5-10 kg/ha. the cpds. are pre- and post emergence herbicides esp. useful against dicotyledons. A typical cpd. is (I; Ar = 2-thienyl, R1 = ethyl; R = H). This was prepd. from ethyl 2-thiophene carboximidate HCl and ethyl amino oxyacetate HCl in pyridine.
公开号:SU886740A3
申请号:SU792790407
申请日:1979-07-26
公开日:1981-11-30
发明作者:Фарж Даниель；Лебуль Жан；Ле Гофф Ив；Пуаже Жильбер
申请人:Рон-Пуленк Агрошими (Фирма)；
IPC主号:

专利说明:

(54) METHODS TO OBTAIN AMIDOXYM DERIVATIVES The invention relates to a process for the preparation of new compounds, namely, amido oxime derivatives of the general foriT-o-dn-Cooi i Lc where R is hydrogen or methyl; R, is hydrogen or alkyl radical containing 1-4 carbon atoms, or alkali metal; Ar is a phenyl radical, substituted by 1–3 substituents, identical or different, selected from halogen atoms and radicals: an alkyl, diy contains 1–4 carbon atoms, hydroxy, alkyloxy, the alkyl part of which contains 1–4 carbon atoms, methylsulfinyl, Methylsulfo1 "1l, trifluoromethyl thio, carboxy, alkyclocarbonyl, the alkyl part of which contains 1-4 carbon atoms, nitro, amino, dialkylamino, each alkyl part of which contains 1-4 carbon atoms, the alkyloxycarbonylamino, the alkyl part of which contains 1-4 atoms carbon; sulfamoyl, optionally substituted by nitrogen with one or two alkyl groups, each alkyl portion of which contains 1-4 carbon atoms, or a 5-chain heterocyclic aromatic radical containing one oxygen, sulfur or nitrogen atom as a hetero atom, and possibly substituted with an од halogen atom, alkyl containing 1-4 carbon atoms, an alkyloxy radical, the alkyl part of which contains 1-4 carbon atoms, an alkylthio radical, the alkyl part of which contains 1-4 carbon atoms, a phenylalkyl radical, and an alkyl part It contains 1–4 carbon atoms, which can be used in agriculture as they possess phytohormone properties. A known method for producing derivatives of amidoxime of the general formula NOH (cng), ing where ft are the substituted benzimidazoline indolyl residues and others ;. Z is methylene unsubstituted or substituted by phenyl; p 0-2, which consists in the interaction of a compound of the general formula R - Z - (CH 2) and-X, where R and Z, n have the indicated times; X is a nitrile, imino ether group, etc., with a compound of the general formula H2N – W, where W is an hydroxy group. The purpose of the invention is the development, on the basis of a known method, of a method for the preparation of new compounds possessing phytohormonal properties. The goal is achieved by the fact that the compounds of the general formula H, 2.N-0-CH-COOR, where R and R yj have the above values, are introduced, in interaction with salts of the imino ether, of the formula Ar-with OCiM, where Ar is defined above, in an organic way such as a basic solvent. Ar-CJ reediv, at a temperature close to .20 ° C. These substances have properties that make them useful in agriculture. they are applied in doses of 1-100 g / hl of water, then they are revealed. interesting phytohormonal properties. Example 1. Getting 0-ethoxycarbonylmethylthiophene carboxamidoxime-2. At a temperature of about 20 ° C, a mixture of 140. g of ethyl .thiophene-2-carboxyimidate ethyl and 104 g of hydrochloride amino ethyl acetate ethyl in 2350 cm of pyridine is stirred for 1 hour. Pyridine is evaporated under reduced pressure (2 mm Hg) at a temperature of about 30 ° C, then the precipitate is mixed In 1 liter of ethylodetate, the formed pyridine hydrochloride is filtered and washed twice with 500 cm of ethyl. acetate. The filtrate is washed with 500 cm of water, decanted, dried over sodium sulfate and decolorized with coal. After filtration and evaporation of the solvent at 30 ° C under reduced pressure (20 mm Hg), a clear oil is obtained which crystallizes in 100 cm and of the propyl ketone. After separation by filtration and drying, 150.7 g of O-ethoxycarbonylmethylthiophene carboxamidoxime-2, melting at 58 ° C, are obtained. After recrystallization in 3.3 parts of isopropyl oxide, the pure product melts at 62c. Examples 2-47. The compounds shown in the table are prepared similarly. (iH-CiOO i
he N
Cjl n
131
73
59
100
(iH: iH.
Ij- -n-a 2.ff
Nz
H
5xlJ
-u
0NS, Nu92130
Tgl
6
bnz
Table continuation
CH 91112
7570
0 (iH.5 NS H 5967-68
.",13
Ns Hg.9249
s1nz
.
ID
NA Nu7339,5
Vg
97
-Yoh
P
V-C1 "C And 0009
".
13
NS Hr89
CF.
14
HC-N 9687
75
, T.kip. 175 C / / 0.2 mm Hg
17
.
V /
H a, n -100 66
IB
 /
2 uh
H
nineteen
H
7590
bp 155 C /
100 / 0.5 mm Hg
97163
21
H
22
H
Sl "f
23
H
l
 / -en
fe 24 j
H
Sl "" r
H
25
26 - / VdOOdzHs "W N 9282
91
8774
80100
99
Bp 142-148 C / / 0.4 mm Hg
9580
27 ff VuHCJOOCieHs, 71141
886740
10 Continuation of the table
146

.. 91124
CHjiCieHj
t
H
five
63
Oil chromate graphed And 1,5655
9198
Oil tras.nosfor82rovanny in oxalate, t.kip.149
T. Kip.
94
10 C / 0.2 mmHg
eleven
jT J
-15
H Na
 ON
 j
-, H Na
-Cl
40 L /
C., H
H
(ii
42
Cl
43
H 75 56

权利要求:
Claims (1)
[1]
The invention of the method of obtaining derivatives of a formula Sd-formula
N-o- H-dopB
Ar-d
Ing
R - hydrogen is methyl;
 hydrogen or an alkyl radical containing 1-4 carbon atoms, or an alkali metal atom;
12
886740 Continuation of the table
186
214
58
100
T.KIP. 178C /
49 / 0.4 MMHg Oil
62
94
; a phenyl radical substituted by 1-3 substituents which may be the same or different and selected from halogen atoms and alkyl radicals with 1-4 carbon atoms, hydroxy, alkyloxy (, alkylthio (.Cf-C4 methylsulfopyl, methylsulfinyl, trifluoromethyl, trifluoromethylthio, yarboxy, alkyloxycarbonyl, the alkyl part of which is (c, -Q, nitro, amino, dimethylamino, alkoxycarbonylamino (; sulfamoyl, ft 1388 & 7A dimethylsulfamoyl-aromatic heterocyclic aromatic hetero-cyclic radical with a set of contents of the package). of nitrogen, and optionally substituted by a halogen atom, 5 alkyl radical (, alkoxy radical (), alkylthio radical (} shsh phenylalkyl, the alkyl part of which contains 1-4 carbon atoms, characterized in that the compound of the general formula AND NO-CH-COOR 1 t R О.14 vvr t in the reaction of interaction with the iminoether salts of the formula C h, in which Ar, R, R | and the indicated values, in an organic solvent, are at ambient temperature. Wednesday.

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同族专利:

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公开号 | 公开日

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SU862812A3|1981-09-07|

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FR2323683B1|1979-07-13|

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FR2323683A1|1977-04-08|

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US8088803B2|2008-07-08|2012-01-03|Incyte Corporation|1,2,5-oxadiazoles as inhibitors of indoleamine 2,3-dioxygenase|

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US8377976B2|2006-09-19|2013-02-19|Incyte Corporation|N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase|

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US8450351B2|2005-12-20|2013-05-28|Incyte Corporation|N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase|

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US8507541B2|2006-09-19|2013-08-13|Incyte Corporation|N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase|

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US9321755B2|2013-11-08|2016-04-26|Incyte Corporation|Process for the synthesis of an indoleamine 2,3-dioxygenase inhibitor|

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法律状态:

优先权:

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申请号 | 申请日 | 专利标题

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FR7527884A|FR2323683B1|1975-09-11|1975-09-11|

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