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CA1110651A - Phenoxy-phenoxy-alkane-carboxylic acid derivatives - Google Patents

Phenoxy-phenoxy-alkane-carboxylic acid derivatives

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Publication number
CA1110651A
CA1110651A CA273,307A CA273307A CA1110651A CA 1110651 A CA1110651 A CA 1110651A CA 273307 A CA273307 A CA 273307A CA 1110651 A CA1110651 A CA 1110651A
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Canada
Prior art keywords
formula
alkoxy
compound
phenoxy
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
CA273,307A
Other languages
French (fr)
Inventor
Gerhard Horlein
Hubert Schonowsky
Peter Langeluddeke
Hermann Bieringer
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Hoechst AG
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Hoechst AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C07C69/736—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

PHENOXYPHENOXY-ALKANECARBOXYLIC ACID DERIVATIVES
Abstract of the disclosure:
Substituted trifluoromethyl-phenoxyphenoxyalkane-carboxylic acids of the formula I

and their functional derivatives have an outstanding effect as selective herbicides in crop plants.

Description

:

65~

German Offenlegungsschrift DOS 2,433,Q67 discloses 4-phenoxy-phenoxy-alkane-carboxylic acids and their derivatives carrying a trif].uoromethyl group in the terminal phenyl ring.
Compounds of this type are characterized by a selectlve herbicidal activity against grass-like weeds.
It has now been found that trifluoromethyl-phenoxyphenoxy-alkanecarboxylic acids having additional substitutents and their functional derivatives have an outstanding effect as selective herbicides in crop plants.
The present invention therefore provides compounds of the formula I
.
, CH

0 - ~ O-C~-COR4 (1) ~R2)n ". ~ in which R2 represents identical or different substituents selected from the group consisting of chlorine or bromine, n is 1 or 2, and R4 is hydroxy, Cl-C8-alkoxy, Cl-C8-hydroxyalkoxy, C2-C10-alkoxy-alkoxy, phenoxy-Cl-C4-alkoxy, chlorophenoxy-Cl-C4-alkoxy, halogeno-`';' Cl-C4-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, C5-C8-cycloalkyloxy, . ~ C5-C8-cycloalkenyloxy, hydrazino, amino, Cl-C4-alkylamino, di~Cl-C4)-alkylamino, phenylamino, phenyloxy, phenylthio (the phenyl group being optionally substituted by halogen, trifluoromethyl, me~hyl, hydroxy, :~ ;

~ ~ ... ~ . . . . .. -.
. .
,,. , ~ . ~ - . ~ .

and/or carbo-(Cl-C2)-alkoxy)- or -Ocat, cat being the cation of an inorganic or organic base.
In the compounds of formula I the CF3 group in the terminal benzene nucleus is preferably in 4-position. Preferably R2 is in the 2-position i.e. adjacent to the -0-alkanecarboxylic acid group; and R4 is preferably (Cl-C8)-alkoxy, especially (Cl-C4)-alkoxy or allyloxy.
The compounds of formula I are prepared by reacting phenoxy-phenols of the formula II

Cl O ~ OH II
3 (R2)n or corresponding phenolates, optionally in the presence of an acid-binding agent, with carboxylic acid derivatives of the formula III

X-CH-COR'4 III

in which X is halogen and R'4 is hydroxy or Cl-C8-alkoxy and, if desired, transforming the compounds of formula I obtained into other functional derivatives of formula I by esterification, saponification, salt-formation, transesterification, or amidation.

In formula III X preferably represents chlorine or bromine;

preferred halogeno-propionic acids are therefore 2-bromo- or 2-chloropropionic acid.
~ 20 The reaction is preferably carried out in organic solvents, :

~2 - 3 -.- ~

~ 5~ HOE 76/F 044 for example ketones such as acetone or diethyl-ketone, carboxylic acid amides such as dimethyl formamide; sulfoxides such asdimethyl sulfoxide; or aromatic hydrocarbons, for example benzene or toluene. When free phenols of formula II
are used, the reaction is preferably carried out in the presence of an alkaline compound to bind the hydrogen halide set free, for example potassium carbonate or a tertiary organic base such as triethylamine.
As soon as the reaction is terminated, the formed hydro~
halic salt is separated by filtration or by addition of water and, after removal of the organic solvent (if any), the ester or other derivative of the carboxylic acid obtained is isolated in known manner.
The derivatives obtained can be purified in usual manner, for example by distillation or recrystallization from an organic solvent or from a mixture of an organic solvent and water.
The different functional derivatives of formula I can be transformed in to one another in known manner. Carboxylic acid esters for example can be saponified by heating with alkaline ` 20 agents, preferably aqueous bases, in the presence of lower alcohols. The alkaline solution is then acidified whereby the free acid separates in the form of crystals or as an oil.
The free acids of formula I, obtained by saponification or by reaction with free halopropionic acids (R4 = OH) can be esterified in usual manner, preferably in the presence of a ;~ catalytic amount of acid catalyst such as sulfuric acid, toluenesulfonic acid, hydrochloric acid, a Lewis acid, for example boron trifluoride, or an acid ion exhanger.
Suitable alcohols for the esterification are, for example, :: . . , . , : , ' .

.
, , :
- : ~ ~ . . - , . , ,-',,: ' '- ~ ~ ' ' ' ' ' ' 65~ -linear or branched aliphatic alcohols having from 1 to 8 carbon atoms, or cyclohexanol.
For the esterification the acid chlorides, which are readily accessible, for example by xeaction of the carboxylic acids of formula I with thionyl chloride, can be used. Reaction of these with the aforesaid alcohols yields the corresponding esters.
Other derivatives of formula I are obtained by reacting the acid chlorides or esters with amines or anilines.
The starting compounds of formula II can be obtained for example, by first preparing trifluoromethyl-phenoxyphenols according to the process described in DT-OS 2j433,066, which are then optionally chlorinated or brominated in known manner.
It is another object of the present invention to provide herbicidal compositions containing the phenoxy-phenoxy-carboxylic acid derivatives of formula I.
The herbicidal compositions according to the invention contain 2 to 95 % of an active compound of formula I. They can be used in the form of emulsifiable concentrates, wettable powders, sprayable solutions, dusts, or granules, in admixture with the usual formulation auxiliaries.
Wet~able powders are preparations that can be uniformly dispersed in water and contain, besides the active ingredient, a diluent or an inert substance, a wetting agent,for example polyoxethylated alkylphenols, or polyoxethylated oleyl- or ` stearyl-amines, alkyl- or alkyl-phenyl-sulfonates, and disper-sing agents, for example the sodium salt of lignin-sulfonic acid, of 2,2'-dinaphthylmethane-6,6'-disulfonic acid, or sodium . . .
~ oleylmethyl-tauride.
." "' ~..................................... _ 5 _ .;' '`,'"''~''~"' , . , .

. :
'';'. ' :

~ 651 HOE 76/F 044 Emulsifiable concentrates are obtained by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethyIformamide, xylene, or aromatic hydro-carbons having a higher boiling point, and adding a non-ionic wetting agent (emulsifier), for example a polyoxethylated alkyl-phenol or a polyoxethylated oleyl- or stearyl-amine.
Dusting powders are obtained by grinding the active ingredient with finely divided, solid substances, for example talc, natural clays such as kaolin, bentonite, pyrophillite, or diatomaceous earths.
Spraying solutions, commercially available as aerosol sprays, contain the active ingredient dissolved in an organic solvent, and in addition thereto a propellant, for example a mixture of fluorochlorohydrocarbons.
Granules can be produced by atomizing the active ing~re-dient on to an adsorptive, granulated inert material , or by applying concentrates of the active ingredient to the surface of a support, for example sand, kaolinite or a granulated inert material, with the aid of an adhesive, for example polyvinyl 20 alcohol, the sodium salt of polyacrylic acid, or mineral oils.
Alternatively, suitable active ingredients may be made into granules, if desired in admixture with fertilizers, in the ; manner commonly used for the manufacture of granulated ferti-; lizers.
` 25 The commercial herbicidal preparations ~ontain varying concentrations of the active ingredients. In wettable powders the concentration of active ingredient varies, for example, ~ from about 10 to 95 %, the remainder being the above formulation ; additives. Emulsion concentrates contain about 10 to 80 ~ of ,: `

.'.'~ ' .

,: . -:, ... . . . .
,'' . ' ', ~ , , ' ~ ;. . ' ' ~
: .
, ~ 51 HOE 76/F 044 active ingredient, while dusting powders mostly contain 5 to 20 ~ of active ingredient and sprayable solutions about
2 to 20 %. In the case of granules, the content of active ingredient partially depends on whether the active ingredient is liquid or solid and on the type of granulation auxiliary or filler used.
For application the commercial concentrates are optionally diluted in usual manner, the wettable powder or emulsifiable concentrate, for example with water. Dusts and granulated formulations as well as sprayable solutions are not diluted further with an inert substance before their application.
The amount applied varies with the external conditions, such -~ as temperature, humidity and the like. The applied amounts , can vary within wide limits, for example in the range of from 0.1 to 10.0 kg per hectare, preferably from 0.3 to 5 kg per hectare.
The active compounds of the invention can be mixed with other herbicides and soil insecticides.
-~ Alternatively, the active compounds of the invention can be mixed with fertilizers whereby a fertilizing and simultane-ously a herbicidal effect is obtained.
The following examples illustrate the invention.
.~
` E X A M P L E S O F P R E P A R A T I O N
..~
General methods .
(A) 0.1 Mol of phenol (II) are dissolved in 50 ml of methylethyl ketone, 0.11 mol of anhydrous potassium carbonate are added and 0.11 mol of halogeno-carboxylic acid ester (III) `~ are added dropwise. The mixture is refluxed for about 16 hours, ice^water is added, the reaction mixture is taken up in , A
,'''";. , ~
,.~. . :

~ 6Sl HOE 76/F 044 methylene chloride, dried over Na2S04, the solvent is distilled off and the crude compound of formula I is crystalli-zed or distilled under reduced pressure.
(B) 0.1 Mol of the ester of Example 1 are dissolved in 270 ml of methanol, 24 ml of 45 % sodium hydroxide solution are added dropwise and the whole is refluxed for 2 hours. The solvent is then distilled off yielding the acid in the form of the sodium salt. The free acid is obtained by adding dilute hydrochloric acid.
(C) 80 ml of thionyl chloride are added to 0.1 mol of the acid of Example 2 and the mixture is refluxed for 6 hours.
The excess thionyl chloride is distilled off and the acid ' ;~ chloride is taken up in toluene.
(D) 0.1 Mol of sodium hydroxide dissolved in 50 ml of water are added to 0.1 mol of an alcohol, phenol, mercaptan, or thiophenol dissolved in 50 ml of toluene. At about 25 to ~ 40C, 0.1 mol of the acid chloride of Example 3, dissolved in ; toluene, are added dropwise. After approximately 1 hour , the organic solution is separated, washed with water and dried over potassium carbonate. After distillation of the solvent, the crude compound of formula I is crystallized or purified by distillation.
(E) 0.1 Mol of triethylamine are added to 0.1 mol of acid chloride (prepared according to Example 3) dissolved in 50 ml of toluene. At 25 to 40C, 0.1 mol of an aliphatic amine or aniline are then added dropwise. The mixture is allowed to react for a further hour and then water is added. The toluene phase is separated, washed with water and dried over sodium sulfate. After distillation of the toluene, the amide or ,'' ' .

''" ' . -:, . ~ '.

~.
. - , .

:
65~

anilide is isolated.
In the following table there are summarized the compounds of formula I which were prepared as described above.

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N N N N

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''', . ~ . - " -, ~ ': ' ' , : . ~ . - ' :
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6Sl ~ o ~a o~ U. _1 o .. .. ..
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~ 651 HOE 76/F 044 FORMULATION EXAMPLES
E X A M P L E A: `
A wettable powder which is readily dispersible in water is obtained by mixing ~5 parts by weight of 2-/4-(4'-trifluoromethylphenoxy)-2-chloro-phenoxy_7-propionic acid isobutyl ester (compound 5 as active ingredient, 64 parts by weight of kaolin-containing quartz as inert sub-stance~
10 parts by weight of the potassium salt of lignin-sulfonic acid 1 part by weight of sodium oleylmethyl tauride as wetting'and dispersing agent, ; and grinding the mixture obtained in a disk attrition mill.
E X A M P L E B:
A dusting powder having good herbicidal properties is obtained by mixing .i 10 parts by weight of 2-/4-(4'-trifluoromethylphenoxy)-2-chloro-phenoxy7- propionic acid isobutyl ester (compound 5) ~` 20 as active ingredient and ,~i, .
90 parts by weight of talcum as inert substanae and grinding the mixture obtained in a cross-beater mill.
,...
E X A M P L E C:
;. . ~ .
~- An emulsifiable concentrate consists of 15 parts by weight of 2-/4-(4'-trifluoromethylphenoxy)-2-. chloro-phenoxy7-propionic acid isobutyl ester (compound 5) ~`~ as active ingredient, 75 parts by weight of cyclohexanone as solvent and . 10 parts by weight of oxethylated nonylphenol (lOAeO) as .~; ~ , .
: - 16 -,.................................... . . ~ , :.
;., . . , - :
,: - . , : . . .. .
.

~65~ HOE 76/F 044 emulsifier.
_ X A M P ~ E D:
A granulate consists, for example, of approximately 2-15 parts by weight of 2-/4-(4l-trifluoromethylphenoxy)-2-chlorophenox~7-propionic acid isobutyl ester (compound 5) as active ingredient and inert granulate carrier materials, for example, attapulgite, pumice granulate and quartz sand.

E X A M P L E S O F A P P L I C A T I O N
Example I
Seeds of various weeds and crop plants were sown in pots.
The pots were treated either immediately or about 3 weeks later when the plants had germinated and developed 3 to 4 leaves, with wettable powder formulations suspended in water.
4 Weeks after the treatment the results were evaluated visually according to the scheme of Bolle tcf. Nachrichtenblatt des Deutschen Pflanzenschutzdienstes 16, 1964, pages 92 to 94):
degree of damage in %
number weeds crop plants ` 1 100 O
2 97.5 to ~100 O to 2.5
3 95.0 to < 97.5 ~2.5 to 5.0
4 90.0 to < 95.0 ~5.0 to 10.0 85.0 to ~ 9o.0 ~10.0 to 15.0 ,~ 6 75.0 to < 85.0 ~15.0 to 25.0 . 7 65.0 to ~ 75.0~25.0 to 35.0 8 32.5 to < 65.0>35.0 to 67.5 ; 9 O to ~32.5 >67.5 to 100 ... .

- .: , . , , . . - ., . . .
., , ~ . ,. , ~ . ,: ,., .. . , :
,. . ~ . .

The result indicated in the following Table I shows that at concentrations of 2.5 kg/ha and in part below compounds 1 and 2 control important annual weeds both in pre-emergence and post-emergence application. The listed weeds all belong to the botanic family of graminaceae (grasses).
Important crop plants remained undamaged.Compounds 3, 5, and 4 had a similar effect.

.
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6Sl ~ a ~ 1 e Effect on weeds and crop plants in pre-emergence and post-emergence tri~ls (preem. and postem.), dosage in kg per hectare .
types of I Compound no. 1 ¦ Compound no. 2 plants preem. I pos~em. I preem. poste~
. 2,5 0,6 ~ 2,5 0,6 12,5 0,6 2.5 0.

~reeds r ; i , _ Ave~a ~atua 4 6 1 7 4 7 1 8 Alopecurus myosuroides 3 5 3 6 3 4 1 5 Setaria lutescens 1 4 4 8 1 4 4 8 Poa tri~ialis 1 3 4 7 1 2 2 6 mul~iflorwm 1 3 3 7 2 3 1 6 Echinochlo~
crus-galli 2 4 1 6 1 3 1 6 ~rop plants~~ .

sugar beet 1 1 1 1 1 1 1 1 rape 1 1 1 1 1 1 1 1 . SOybean 1 1 1 1 1 1 1 1 . pea 1 1 . 1 1 1 1 1 1 dwarf bean- 1 1 2 1 1 1 3 1 horse bean 1 1 1 1 .. 1 1 1 1 cotton 1 1 3 1 1 1 ~ 1 tomatoe 1 1 1 1 1 1 1 1 tobacco 1 1 1 1 1 1 1 1 carrot 1 1 1 1 1 1 1 : cabbage 1 1 1 1 i 1 1 1 salad 1 1 1 1 1 1 1 ... . . -.: . . , :
. .: -~ : :

.. , : ' . . - ~ ', . ~ :
~ '': .' '' " ', ' ' ' :

1116~65:~

E X A M P L E II
Seeds of Echinochloa crus-galli (barnyard grass) were sown in pots sealed at the bottom. At the same time, 14 day old rice seedlings were planted in pots of the same type.
One week later, when the barnyard grass started to germinate, the pots were filled with water so that the water stood 1 cm above the soil surface. Suspensions of the invention compounds were then sprayed on the standing water. The results evaluated 4 weeks after the treatment are indicated in Table II. It can be seen that compounds 2 and 4 kept the barnyard grass under control without doing any noticeable harm to the rice.
Similar results were obtained with compounds 1, 3 and 5.
The following compound A (from DT-OS 24 33 067) CF3- ~ -O- ~ -O-CH-COOCH3 A
,,' .
which was used for comparison, controlled Echinochloa almost completely when applied in a concentration of 0.62 kg per hectare, but it did considerable damage to rice T a b l e II
Effect on Echinochloa and transplanted rice ,i ~
Compound , ha~~ Echinochloa . rice -~ 2~5 , l 3 ,; 2 1,25 l 2 0 62 ~ 4 . 4 1.25 2 2 . 0 62 ~ l .

~,; A l,25 l 9 0.62 2 8 ,' .
_ ~o--. :
, ,. ' . . ' : ' :'. , , 6~

E X A M P L E III
In a pre-emergence trial using some of the compounds of the invention against Setaria, Echinochloa and/or Lolium the following results were obtained:
T a b l e III
.
Effect of the compounds of the invention in pre-emergence application.
effect on Compound dose active Setaria Echinochloa Lolium No. c~und.
ka/ha _ _ ; 1 2.5 1 1 -0,6 2 4 -2 2.5 2 0.6 4 3 3 2.5 2 3 0.6 5 4 ~ 4 2.5 1 2 ;~ 0~6 3 4 ,~ 5 2.5 ~. 0,6 2 . 4 ".' 15 2.5 7 - . -~, 26 1.25 4 28 2.5 6
5.0 - - 6 29 5.0 - _ 7 ': 30 5~.0 - - 7 .' ' .
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Claims (9)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. Compounds of the formula I

I

in which R2 represents identical or different substituents selected from the group consisting of chlorine or bromine, n is 1 or 2, and R4 is hydroxy, C1-C8-alkoxy, C1-C8-hydroxyalkoxy, C2-C10-alkoxy-alkoxy, phenoxy-C1-C4-alkoxy, chlorophenoxy-C1-C4-alkoxy, halogeno-C1-C4-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, C5-C8-cycloalkyloxy, C5-C8-cycloalkenyloxy, hydrazino, amino, C1-C4-alkylamino, di(C1-C4)-alkylamino, phenylamino, phenyloxy, phenylthio, (the phenyl group being optionally substituted by halogen, trifluoromethyl, methyl, hydroxy, and/or carbo(C1-C2)-alkoxy), or -Ocat, cat being the cation of an inorganic or organic base.
2. A compound as claimed in claim 1, wherein R4 is alkoxy having 1 to 8 carbon atoms or allyloxy.
3. A compound as claimed in claim 1 having the formula
4. A compound as claimed in claim 1 having the formula
5. A compound as claimed in claim 1 having the formula
6. A compound as claimed in claim 1 having the formula
7. A compound as claimed in claim 1 having the formula
8. A process for preparing a compound of formula I as claimed in claim 1, which comprises reacting a phenoxy-phenol of the formula II

II

with a carboxylic acid derivative of the formula III

III

in which X is halogen and R'4 is hydroxy or C1-C8-alkoxy and, if desired, transforming the compounds of formula I obtained into other functional derivatives of formula I by esterification, saponification, salt-formation, transesterification or amidation.
9. A method of combating weeds, which comprises applying to the infested area an efficient amount of a herbicide containing as active ingredient a compound of formula I as claimed in claim 1.
CA273,307A 1976-03-08 1977-03-07 Phenoxy-phenoxy-alkane-carboxylic acid derivatives Expired CA1110651A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2609461A DE2609461C2 (en) 1976-03-08 1976-03-08 α-4- (trifluoromethylphenoxy) phenoxy propionic acids and their derivatives, processes for their preparation and herbicidal compositions containing them
DEP2609461.1 1976-03-08

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AT (1) AT350839B (en)
AU (1) AU504699B2 (en)
BE (1) BE852210A (en)
BR (1) BR7701376A (en)
CA (1) CA1110651A (en)
CH (1) CH626227A5 (en)
DD (1) DD128710A5 (en)
DE (1) DE2609461C2 (en)
DK (1) DK99077A (en)
ES (1) ES456459A1 (en)
FR (1) FR2343715A1 (en)
GB (1) GB1563850A (en)
GR (1) GR71188B (en)
HU (1) HU179718B (en)
IE (1) IE44423B1 (en)
IL (1) IL51605A (en)
IT (1) IT1078686B (en)
NL (1) NL7702305A (en)
OA (1) OA05588A (en)
PH (1) PH12591A (en)
SU (1) SU673136A3 (en)
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ZA (1) ZA771297B (en)

Families Citing this family (5)

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DE2961917D1 (en) 1978-01-18 1982-03-11 Ciba Geigy Ag Herbicidal active unsaturated esters of 4- (3',5'-dihalogenpyridyl-(2')-oxy)-alpha-phenoxy propionic acids, process for their preparation, herbicidal compositions containing them and their use
JPS6033389B2 (en) 1979-02-22 1985-08-02 日産化学工業株式会社 Heterocyclic ether phenoxy fatty acid derivative, its production method, and herbicide containing the derivative
US4391628A (en) * 1981-02-16 1983-07-05 Ciba-Geigy Corporation 2-[4-(6-Haloquinoxalinyl-2-oxy)phenoxy]propionic acid esters
DE3219789A1 (en) * 1982-05-26 1983-12-01 Bayer Ag, 5090 Leverkusen PHENOXYPROPIONIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES
DE3318354A1 (en) * 1983-05-20 1984-11-22 Bayer Ag, 5090 Leverkusen OPTICALLY ACTIVE PROPIONIC ACID DERIVATIVES

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DE2433067B2 (en) * 1974-07-10 1977-11-24 a- [4-(4" Trifluormethylphenoxy)-phenoxy] -propionsäuren und deren Derivate, Verfahren zu ihrer Herstellung und diese enthaltende herbizide Mittel Hoechst AG, 6000 Frankfurt ALPHA SQUARE BRACKETS ON 4- (4 'TRIFLUORMETHYLPHENOXY) -PHENOXY SQUARE BRACKETS ON PROPIONIC ACIDS AND THEIR DERIVATIVES, METHOD FOR THEIR PRODUCTION AND HERBICIDAL AGENTS CONTAINING THESE
CS185694B2 (en) * 1974-07-17 1978-10-31 Ishihara Sangyo Kaisha Herbicidal agent

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JPS52108939A (en) 1977-09-12
IE44423B1 (en) 1981-11-18
IL51605A0 (en) 1977-05-31
BR7701376A (en) 1978-05-02
DE2609461A1 (en) 1977-09-22
HU179718B (en) 1982-11-29
DK99077A (en) 1977-09-09
FR2343715A1 (en) 1977-10-07
FR2343715B1 (en) 1981-12-11
IT1078686B (en) 1985-05-08
AU504699B2 (en) 1979-10-25
ES456459A1 (en) 1978-02-16
ZA771297B (en) 1978-01-25
ATA147477A (en) 1978-11-15
AU2301677A (en) 1978-09-14
SU673136A3 (en) 1979-07-05
IL51605A (en) 1980-10-26
DE2609461C2 (en) 1984-11-22
GR71188B (en) 1983-04-11
PH12591A (en) 1979-06-27
IE44423L (en) 1977-09-08
CH626227A5 (en) 1981-11-13
OA05588A (en) 1981-04-30
GB1563850A (en) 1980-04-02
AT350839B (en) 1979-06-25
NL7702305A (en) 1977-09-12
BE852210A (en) 1977-09-08
TR19297A (en) 1978-11-01
DD128710A5 (en) 1977-12-07

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