Herbicide agent

专利摘要:
Novel 7-(Aryloxy)-2-naphthoxyalkanecarboxylic acid derivatives of the formula I in racemic or separated isomeric form, have herbicidal activity.
公开号:SU1445550A3
申请号:SU853952650
申请日:1985-09-16
公开日:1988-12-15
发明作者:Харре Михаэль；Крюгер Ханс-Рудольф；Арндт Фридрих；Руш Райнхарт
申请人:Шеринг Аг (Фирма)；
IPC主号:

专利说明:

The invention relates to x; 1 micron; - ka means of controlling weed and undesirable vegetation).
The purpose of the invention is to increase the germicidal activity of the agent based on aryloxyalkanoiccarboxylic acid derivatives.
Below are the active substances of the herbicidal agent, the method of their preparation and examples illustrating the effectiveness of this agent.
Example 1, Production of (2-chloro-4-trifluoromethyl-Noxoyl) ethyl ester -2-naphthyloxy propanoic acid (compound No. 1).
6.14 g (18.12 mmol) of 7- (2-chloro-4-- trifluoromethylphenoxy) -2-o1 synaphthalene 2.51 g (18.12 mmol) of potassium carbonate, 2.6 ml (19.9 mmol 2-brampropiopaic acid ethyl ester and 150 ml of 2-buta gon are suspended and heated for a period of 5 hours at the boiling point of the mixture under reflux. After that, the solution is stilled in a hot state, evaporated and chromatographed on silica gel (hexane-ethyl acetate 9: 1). 6.1 g (77%) of the desired substance are obtained in the second ratdemic mixture.
Similarly, they synthesize druh or compounds (see,),
EXAMPLE 2 Preparation of 2- (R) (2-chloro-4-trifluoromethylphenoxy) -2-naphtshuxy-propionic acid ethyl ester (compound No. 32),
5 g of potassium carbonate and 10 g of silicone are suspended in 200 ml of dimethyl sulfoxide, unmixed in Te-jei-n-ie overnight under anhydrous conditions, and 6.02 g of 1- (2-chloro-4- rifluoromethylphenoxy) -7-hydroxynaphthaliE1a. Then stirred for 1 h; at room temperature, a solution of 5 g of ethyl EFI is added slowly;), M
2- (S) - (p-tolylsulfonyloxy) propionic acid in dimethyl sulfoxide and stirred for 2 hours. Immediately thereafter, the reaction mixture is hydrated through celite, and the extract is extracted, the sodium chloride is washed with a solution of sodium chloride. , dried over magnesium sulphate and evaporated. After chromatography on a column of silica gel {hexane-ethyl acetate 9: 1), the target substance is obtained in an amount of 7 g (89%)
Under similar conditions, other compounds are prepared (see Table 2),


PRI me R 3 Determination of herbicidal activity during post-emergence application,
Experimental plants grown under greenhouse conditions up to a certain growth stage are treated with a herbicidal agent containing, in wt.%: Active substance 25, cyclohexanone 13, xylene 55, nonylphenol polyoxyethylene 2, calcium dodecylbenzenesulfonate 3, emulsified in 500 l of water at a rate of 3 kg active substance per hectare. Evaluation of the herbicidal action was carried out 3 weeks after treatment on a scale from 0 to 4 | O - no effect; 4 - full of death of plants.
The results of the experiments are presented in table. 3
PRI me R 4. Determination of Herbicidal Activity.
Experiments were performed under the conditions of Example 3 with the only difference that the dose of the active substance was. 0.3 kg / ha. The results of the experiments are presented in Table 4.
EXAMPLE 5. Comparative experience, fishing practices are similar to the irimer 3, Rating scale: O - no damage to plants; 1 - 10-20% lesion; 2 - 30-70% lesion; 3 - 80-90% lesion; 4 is full of plants.
In this experiment, compound K 34 and the known compound — analogue (A): ethyl, 2- (K) ester (3 chloro 5-trifluoromethylpyridyl-2-oxi) -1-naphthyloxy propionic acid were used. The results of the experiment are presented in gab, g. five.
The results of the experiments indicate a high efficacy of the herbicidal agent. It has a selectivity of action for crops.
V
about rmu l and
goiter
A herbicidal agent containing an active substance, an aryloxyalkanecarboxylic acid derivative, a solvent, and a surfactant, is THEREFT, characterized in that, in order to increase the herbicidal activity, it contains, as an active substance, an aryloxyapanecarboxylic acid derivative of the general formula

four
CF ,, RrC-Y, X ..
de W is hydrogen or chlorine;
X is CH or N; R, is methyl ethyl, isopropyl; Rz. - hydrogen or methyl; Y - ORj, SR, amino, ethylamino, i
butylamino, phenylamino, di-I-ethylamino or dibutylamino group; tj is hydrogen, sodium, C, Cd-alknl,
2-methoxyethyl, 2-ethoxyethyl, 15 allyl, propargyl, cyclohex-. Se, 3-bromopropyl, 2-cyanoethyl, phenyl, 2-methylphenyl, (1, 2, 3, 4-bis-o-isopropylidene) R,
xylityl;
R is ethyl, benzyl, provided that when I, means ethyl or isopropyl, then R is hydrogen, R, is ethyl, X is CH, W is chlorine,
20
17.09.84 - racemic mixtures of the active substance;
15.07.85 with R - isomers of the active substance.
Table 1 Active substances of general formula
 i
1440550
as a solvent. shchloheksanonon and xylene, and as a surface-active substance - nonylphenylpolyoxyethylene and dodets1-shbenzg1L- calcium sulfonate with the following content of components, wt.%:
Specified active substance
Cyclohexanone
Xy-floor
Nonylphenylpolyoxyethylene Calcium Dodeshch-Shbenzenesulfonate
Priority featured
17.09.84 - racemic mixtures of the active substance;
Active substances in general: formulas
Table
cr3- 0 0 3ToT ° C "iPrC-Y
-X Q
SI
sn
N CH
sn th with and
sn
with and
SI
sn
Chlorine Methyl Zyloxy Hydrogen
2-Ethoxythyloxy
   Etipoxy
2 Mstoxy ethylokea
   Metsyuksi - - Hydroxy PropargylOKCV
n-butyl hydroxy
Ln jiuksi
Isopropyl-Osk
n-propyl oxy
Table 3
Herbicidal activity in post-emergence application (dose of active substance 3 kg / ha)
Active substance, K
T
Experienced plants, tivnost in points
I
Cabbage
.one.
Chamomile
2
3
4 4
(R-isomers)
456.1 (0.5U)
-f-51,4 (0,5)
-61.9 (0.5)
+50.4 (0.505)
+57.7 (0, 540)
+37 (0.5)
+67.3 (0.52)
+62.5 (0.52)
1.5633 +53.9 (0.515), 5493 + 3S, 2 (0.510)


1.5562 155 (0.5)
45
Continuation of table 3
91445550
Continuation of table 3
ten
Continuation of table 3
------ -i I I 1 I f I I t
oooooooooooooooo
oooooooooooooooo
oooooooooooooooo
n HO fn GL fo m rO43- t- f t- t - t r- r
oommforororo r j t J 5: f- -
 } - J-4f t-r t f J l t l fO
 .) t- t J I f -J
).
f-d-} - fvt- r4t f l -4 t- 3 l f t f
t4} - 3 4} - t t f J l 4} - J -S - J
l- 3-- f-tf- - x 3- f- t- r- -3 -J
CNIvOr OTNOCOCNrn- tLO Dr COCT O OrOfOrOrOrOnn-
to fa a s c;
Yu cti H
-4-.f fGOCN
r nroCVi 1СЛrO Nf-О П
-d- r 1-COCs CN
f fC rOi N
O-} - 3O- j-SLGCHO
st in rOr iГЧC i
i- E- J-COr) O
- r -fOr JGch |
about about cxi
m - with s
oh oh oh
 - ABOUT
ABOUT
ABOUT
about (
(N

权利要求:
Claims (2)
[1]
Claim
A herbicidal agent containing an active substance, an aryloxyalkanecarboxylic acid derivative, a solvent and a surfactant, characterized in that, in order to increase the herbicidal activity, it contains as an active substance an aryloxy alkanecarboxylic acid derivative of the general formula
1 445 550
W c ^ - <i! ^o -ic ^ ^OCTW V ^{Y. x} 0 where W is hydrogen or chlorine;
X is CH or Ν;
R ₍ is methyl ethyl, isopropyl; R1 is hydrogen or methyl;
Y is ORj, SR ₄ , amino, ethylamino, 1 butylamino, phenylamino, diI ethylamino or dibutylamino;
R - hydrogen, sodium, C ₄ -C ₅ ~ alkyl, 2-methoxyethyl, 2-ethoxyethyl, 15 allyl, propargyl, cyclohex-. sil, 3-bromopropyl, 2-cyanethyl, phenyl, 2-methylphenyl, (1, 2,3,4-bis-o-isopropipidene) · xylityl; 20
R4 is ethyl, benzyl, provided that when R ₍ means ethyl or isopropyl, then is hydrogen, R Is ethyl, X is CH, W is chlorine, the solvent is cyclohexone and xylene, and as a surface - the active substance is nonylphenylpolyoxyethylene and calcium dodecylbenzeplsulfonate with the following content of components, max.
Specified Active Substance25
Cyclohexanone15
Xylene55
Nonylphenylpolyoxyethylene2
Dodecip calcium benzenesulfonate 3
Featured Priority
09/17/84 - racemic mixtures of the active substance;
07.15.85 at R - isomers of the active substance.
Active substances of the general formula
Table 1
OCPtRf CY ¹ 2 _(i O (racemic mixtures)
Compound No. X WR _zY Mp S ha OR Pr 1 • 2 2> 4 5 6 7 1 CH Chlorine Me type Hydrogen Ethyloxy 1 .5630 2 CH ——— _ ^and _ - ^{, 1} _. 2-ethoxyethyloxy 1.5540 ABOUT N- ⁿ -Ethyloxy 1 .5640 4 CHIsopropyl_ ^tg _ 1.5521 5 N Hydrogen Methyl _P__ - ^and - 61-63 6 CH Chlorine _eleven_2-methoxyethyloxy 1.5586 7 CH _eleven_ Methyloxy 1.5696 8 CH Hydrogen Mr. idroxy 150 9 CH -. ^tt - !1_Propargyloxy 1.5705 10 CH _H_ _P - _eleven _ o-pa 150 eleven CH__eleven_n-butyloxy 1.5542 12 CH- ⁿ - _yy_ Allyloxy 1.5641
Continuation of the table. 1
1 2 3 4 thirteen cn14 cn - about fifteen cn- ”- 16 cn - - ⁿ - 17 CH_J r _ 18 CH -. ^gg - 19 CH__ f f _ 20 pH21. cn eleven _ 22 CH __eleven _ 23 CH_! 1 _ 24 sn."and_ 25 cnί1 ~ 26 cn -1'_ 28 cn"F f" 29th cn Chlorine Methyl thirty cn ._ ^P - 27about cn _P_ _ and 28. CHEthyl 29th CH - ⁿ - Methyl thirty cn Hydrogen 31 cn Chlorine
i 5- 6 7 Phenyloxy 90-93 Benzylthio 1.6052 -J ¹ - Ethylthio 1.5871 Cyclohexyl-oxy 1.5582 2-Methyl (Enyl-oxy 1.5823 Ji _ 2-methylbutyl-oxy 1.5484 Ji _ Z-Bropropi 1.5671 J1_ Amino 115 Ethylamino 112 _J1 _ Diethyl amino; '' LOO _f1 _ Phenylamino 146 Butylamino 83 _eleven _ Dibutylamino 1.5590 and _ 2-cyanoethyloxy 1.5656 __ ^rl - Ethoxycarboneil amino 112 Hydrogen 1- (methoxycarbonyl) ethylamino 1.5600 _JI_ Ethoxycarbonyl methyl thio 1.5698 __ eleven _ 1,2: 3,4-bis0-iso-propylidenexylythyloxy 1.5439 _Jf - Ethyloxy 1.5586 Ethyloxymethylⁿ - 1.5572 Hydrogen - 1 .5551 _Jt_ n-propyloxy 1.5590
I 445550
Active substances of the general formula
-ochjvc-y
1 L _(| o (R-isomers) n
+ 51.4
AND
Sat (0.5)
Ϊ!
[2]
2-Ethoxy3TIloxy
EthylocSI
61.9 (0.5)
HE
It
2-Methoxy + 50.4 ethyloxy
CH
Methyloxy, 5 548
1·
Hydroxy
CH
Propargyloxy .5606 +67.3 (0.52)
CH ft
T!
n — Butyl — hydroxy +62.5 (0.52)
CH
I!
(1
Allipoxy +53.9 '(0.515)
CH f g '
Isopropyl- 1.5493 oxy + 39.2 n-Propyloxy
155 (0.5)
1!
CH
1.5562
Table 3 45 Continuation of table.Z Herbicidal activity in after-Active ve- Experienced plants, effec germination application (dose assets-society, No. TIB NOSE TH in points new substances 3 kg / ha) G “' Cabbage Chamomile Active ve- Experimental plants, effective fifty society, no. j activity in points 4 D 4 1Cabbage Chamomile5 4 4 1 / 455 6 4 4 2 4 4 7 4 4 3 4 4 . 8 4 4
9 1445550
Continuation of table.Z, Continuation of table.Z
Active substance, ₽ Experienced plants, efficiency in points 5 · Active substance, ₽ Experienced plants, efficiency and points Cabbage Chamomile Cabbage 9 4 4 10 26 4 4 10 4 427 4 4 eleven 4 428 4 4 12 4 4 fifteen 29th 4 4 thirteen 4 4thirty 4 4 14 4 4 20 31 4 4 fifteen 4 432 4 4 16 ' 4 433 4 4 · 17 4 4 25 34 4 4 18 4 435 4 4 19 4 4 thirty 36 4 4 20 4 437 4 4 21 4 438 4 4 22 4 4 35 39 4 Δ 23 4 440 4 4 24 4 4 40 41 4 4 25 4 442 4 4
eleven
1 2 nJ
I
To i
Post-emergence herbicidal activity (active substance dose 0.3 kg / ha)
Soybean 1111 - - - 11 liter11 1 x1 1 f1 1 g1 P *! about about about about I cft11 ί 11 x11 1 x1 ! Iΐ ° about about about ! I 1 L 11 o11 1 x1 rh1! °1 about about about elevenf tt ha 11 1 s Jx- I 1 f h 1 co CO with 1 x F 1 1 joint venture ir: 1 ! x! 1 i1 1 x1 t ha 1 1 1 o1 No.! with With with i s1 11 11 1 I1 1 f1 1 x1 ί o1 to 1 ! <r <G ’ <r ! TO1 eleven1 ha £ ! 1 o X 1 1 o well 1 i X 1 1 o1 to1 φ i ! <r1 <r <r <t I 1 1 x 1 haί 1 CO1 1 g I 1 1 P <ί x1 φ h !1 <r <r 1 "1 1 i1 1 x1 1 liter1 £1 <r<r ί o1 1 aί ΐ ha1 1 and1 ί ha1 1 "s1 I! <r <r t ΘI ! ha 1 b1
I
I
I
I
I
I I
I <g
I I o
I
I
I
I I O I
I
I I
I
I
About i
I
I
I
I <7 I
I
I
I
I <7 /
<r
I <7 I
I
I
I I
I <7 I
I
I
I
I
I <7 I
I
I
I
I
I <7 <7 <7
I I <7 I
I
I
I ha1 x 1 o- <r <r <r ί ha 1 1 x 1 1 Θ 1 1 I 1 1 g1 o 1 <r<r 1 rh1 11 t * I 1 f 1 1 x 1 1 i 1 ί f 1 1 x 1 1 x 1 1 i 1 1 f 1 1 o1 o & 11 mid KO about*
I
I
I <7 I
I
I
I
I
I
I
I <7 |
I
I I
I
I
I <7
I
I
I
I
I
I
I
I
With
I I O I <7 I
thirteen
1 S3 LT | 1 <u 1 ft in i F ¹ X 1 C. K ! OK s t t to
R 1i 1 tt eleven Ό I co K 1 1 F t- 1 F I U "eleven IH i m !i
about 1 x 1 to K!w To I With With e-j v- about With h ABOUT about about
X t a: F 1 l) K 1 with X f ¹S S X 1 η f K 1 . X b R. 1-
To I With X! q About 1 I X 1 S About 1 θ IN (- About 1 f > h 1 and 1 a X Ϊ ω ω ί X IN 1 about ABOUT ( R. P 1
S f £ M i about not> m And 1 and X " 1 ti £ With ¹ ! 1 about f ° L to to }1 ~~ ~ and ⁱⁿi f
c0 M 1 t— with h— With with ς— with ABOUT'with t— about about about in ig $ 4 • h A(TO L gh hech W i h- about ABOUT about about - ABOUT * about about about
| -------------------------------1 f --1from 1 ! ° and I 1 to E- 1 1 No. υ 1 1 to F 1 <{ 1 n S 1 With 1 " F 1 1 < And 1

类似技术:

---

公开号 | 公开日 | 专利标题

---

JP2811121B2|1998-10-15|Heterocyclic compounds

---

JP2828186B2|1998-11-25|Acrylate-based compounds, their preparation and fungicides

---

JP2632863B2|1997-07-23|Aryloxycarboxylic acid derivatives and their production

---

JP2725274B2|1998-03-11|Pyrazole derivatives and selective herbicides

---

EP0083055B1|1986-09-17|Tetrahydrophthalimide compounds, and their production and use

---

RU1792280C|1993-01-30|Method of struggle against weeds

---

CH631711A5|1982-08-31|COMPOUNDS AND COMPOSITIONS WITH HERBICIDE PROPERTIES AND THEIR PREPARATION METHOD.

---

CA1101435A|1981-05-19|Herbicide

---

HUE027872T2|2016-11-28|Novel process for statins and its pharmaceutically acceptable salts thereof

---

JPH0725753B2|1995-03-22|Quinoxalinyloxyphenoxy compound and herbicide composition

---

SU1445550A3|1988-12-15|Herbicide agent

---

EP0481512A1|1992-04-22|3-Alkoxyalkanoic acid derivative, process for preparing the same and herbicide using the same

---

JPH0753719B2|1995-06-07|Triazine derivative, production method thereof and herbicide containing the same as active ingredient

---

EP0094102A2|1983-11-16|1-| pyrrolidine derivatives, and process for their preparation

---

DE69628750T2|2004-04-29|NEW ANTIVIRAL, HOMOCARBOZCLIC NUCLEOSIDE DERIVATIVES OF SUBSTITUTED PYRIMIDINE DIONES, METHODS FOR THEIR PRODUCTION AND COMPOSITIONS THAT CONTAIN THEM AS AN ACTIVE COMPONENT

---

CN111825585B|2021-12-14|Aryl sulfide containing benzylamine structure and synthesis method and application thereof

---

KR20010100825A|2001-11-14|Herbicidal benzoyloxy carboxylates and carboxamides

---

EP0265305B1|1991-06-12|5-pyrazolone derivatives, process for their preparation, their use as herbicides and compositions containing them

---

SU1584737A3|1990-08-07|Method of fighting weeds

---

EP0298752A2|1989-01-11|Mercapto-substituted pyridine compounds and process for preparing the same

---

US4582526A|1986-04-15|Carbamic acid ester herbicides

---

JP2734692B2|1998-04-02|A cyanoacetamide derivative and a plant disease controlling agent containing the same as an active ingredient.

---

KR790001258B1|1979-09-18|Process for preparing 2-4-5-halogen substiuted pyridyl-2-oxy alkanecarboxylic acids and derivatives there of

---

US5114466A|1992-05-19|1-|-3-halogeno-4-|-2-pyrrolidinone derivatives and herbicides containing them

---

EP0040478A1|1981-11-25|Process for preparing pyridine derivatives and intermediates useful in the process

同族专利:

---

公开号 | 公开日

---

BR8504493A|1986-07-15|

---

HUT41372A|1987-04-28|

---

IL76399D0|1986-01-31|

---

DE3562138D1|1988-05-19|

---

DK421085D0|1985-09-17|

---

EP0179015A1|1986-04-23|

---

HU200739B|1990-08-28|

---

ES8700650A1|1986-11-16|

---

FI853561L|1986-03-18|

---

IL76399A|1990-01-18|

---

EP0179015B1|1988-04-13|

---

ES546992A0|1986-11-16|

---

AR240042A1|1990-01-31|

---

KR860002447A|1986-04-26|

---

DK421085A|1986-03-18|

---

PH24350A|1990-06-13|

---

US4709077A|1987-11-24|

---

FI853561A0|1985-09-17|

引用文献:

---

公开号 | 申请日 | 公开日 | 申请人 | 专利标题

---

---

US3979437A|1973-09-19|1976-09-07|Mobil Oil Corporation|Substituted phenoxybenzoic acids and derivatives thereof|

---

FR2388789B1|1977-04-27|1980-04-18|Seuref Ag|

---

EP0003114B1|1978-01-18|1982-01-27|Ciba-Geigy Ag|Herbicidal active unsaturated esters of 4- -oxy)-alpha-phenoxy propionic acids, process for their preparation, herbicidal compositions containing them and their use|

---

DE2805981A1|1978-02-13|1979-08-16|Bayer Ag|PHENOXYPROPIONIC ACID DERIVATIVES, PROCESS FOR THEIR PRODUCTION AND USE AS HERBICIDES|DE3731801A1|1987-09-22|1989-03-30|Bayer Ag| ARYLOXY-NAPHTHALIN-2-YL-OXY) -ALKANCARBONIC ACID DERIVATIVES|

---

DE3733067A1|1987-09-30|1989-04-13|Bayer Ag| --PROPIONIC ACID DERIVATIVES|

---

DE3823318A1|1988-07-09|1990-02-22|Bayer Ag| ARYLOXYNAPHTHALINE WITH SUBSTITUTES TIED ABOVE SULFUR|

---

DE3829586A1|1988-09-01|1990-03-22|Bayer Ag|DISUBSTITUTED NAPHTHALINE, METHOD FOR THE PRODUCTION AND THEIR USE OF HERBICIDES|

---

DE3928988A1|1989-09-01|1991-03-07|Bayer Ag|ARYLOXYNAPHTHALINE DERIVATIVES|

---

DE4111619A1|1991-04-10|1992-10-15|Bayer Ag| -CARBONIC ACID DERIVATIVES|

---

DE4202053A1|1992-01-25|1993-07-29|Bayer Ag|PYRIDYLOXY NAPHTHALINE|

法律状态:

优先权:

---

申请号 | 申请日 | 专利标题

---

DE19843434447|DE3434447A1|1984-09-17|1984-09-17|7-Aryloxy-2-naphthyloxyalkane carboxcylic acid derivatives, process for the preparation of these compounds and compositions having herbicidal action containing them|

---

DE19853525562|DE3525562A1|1985-07-15|1985-07-15|Optically active 2--[7--2-naphthyloxy]propanoic acid derivatives, their preparation, and herbicides comprising them|

---