FR2535719A1 - PHENOXY-5 BENZOYL DERIVATIVES OF PENTITOLS, METHODS FOR PREPARING THE SAME, AND HERBICIDAL ACTION PRODUCTS CONTAINING SUCH COMPOUNDS - Google Patents

Abstract

5-PHENOXY BENZOYL DERIVATIVES OF PENTITOLS. THEY MEET THE FORMULA: (CF DRAWING IN BOPI) IN WHICH ONE OF THEY REPRESENTS A RADICAL (TRIFLUORO-METHYL-4 PHENOXY) -5 BENZOYL CARRYING A HALOGEN OR A RADICAL -CN OR -NO IN POSITION 2 ON BENZOYL , AND THE COUPLES THAT WE CAN FORM WITH

Description

The present invention relates to new 5-phenoxy benzoyl derivatives

  pentitols, processes for their preparation, and products with herbicidal actions containing

such compounds.

  So far we did not know any ben derivatives

  zoylics of pentitols having a biological action.

  The technical problem faced by the present inventors was to develop new chemical compounds which had an advantageous herbicidal action. This technical problem is solved, according to the invention, by means of a product which contains, as new active ingredients, at least a 2-phenoxy-benzoyl derivative of pentito corresponding to the general formula I CH oy

CH O Y

i

CH O Y 3 (I)

CH O Y 4

CH 2 O Y 5

  in which one of the substituents Y represents a radical: U Co

Ul CO -

I i

F 3 C O

I (II)

  W and the pairs that can be formed each time with the other substituents Y each represent a radical

R

  R 1 and R 2 represent, independently of one another, hydrogen, a C 1 -C 10 alkyl radical optionally carrying one or more substituents taken from the group consisting of halogens, C 1 -C 6 alkoxy, phenoxy radical and radicals

  halo-phenoxy, an aryl- (C 1 -C 3) alkyl radical

  kyle optionally bearing one or more substituents taken from the group consisting of C 1 -C 6 alkyls, halogens, C 1 -C 6 alkoxy, nitro radical and radical

  trifluoromethyl, a hydrocarbon radical cy-

  cloaliphatic C 3 -C 8, or an aromatic hydrocarbon radical optionally carrying

  of one or more substituents taken in

  appears to be C 1 -C 6 alkyl, halogen, C 1 -C 6 alkoxy, radical

  nitro and the trifluoromethyl radical, or

  together and with the carbon atom that

  carries a cycloaliphatic hydrocarbon radical

  C 3 -C 8, Z represents a nitro or cyano radical or a halogen atom, U represents a hydrogen or halogen atom and W represents a hydrogen or halogen atom, a cyano radical or trifluoromethyl or

C 1 -C 4 alkyl radical.

  The products according to the invention can be used, it was impossible to predict, for the control of weeds, even when we must spare cultivated plants, and they enrich

  so much the state of the art in this area.

  The products conform to the invention

  come, for example, to fight selectively

  rebellious weeds, such as Viola, Galium, Centaurea,

  Amaranthus, Ipomea, Fagopyrum, Sesbania, Datura, Chrysanthemus

  mum, Polygonume Matricaria, in crops including soybean, wheat, rice, barley, peanut and

potato.

  The products in accordance with the invention may be applied pre-emergence, but they are better applied post-emergence. They have the advantage of being very effective already at a low dose, for example at doses of 0.05 to 5. 0 kg of

active ingredient per hectare.

  Among the compounds according to the invention, there are some which are indicated by an optimal action of the type of which we have just mentioned. These are in particular those in the formula I of which R 1 and R 2 each represent, independently of one another on the other hand, a hydrogen atom or a methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, 2,2-dimethylpropyl, n-pentyl, n-octyl, n- decyl, chloromethyl, bromomethyl,

  fluoromethyl, dichloromethyl, trifluoromethyl, trichlo-

  romethyl, methoxymethyl, ethoxymethyl, phenoxymethyl, 4-chlorophenoxymethyl, chloroethyl, bromethyl, ethoxy-2

  ethyl, 2-phenoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl

  hexyl, benzyl, 2-phenylethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl,

  4-methoxyphenyl, 4-nitro-phenyl or 2,4-dichlorophenyl.

  Among the compounds according to the invention whose action is particularly remarkable, those in formula I of which: 1) Y 1 represents a radical:

U CO-

l

CF 3 O G (II '

3 ITI

  W and each of the pairs (Y 2, Y 3) and (Y 4, Y 5) represents an optionally substituted methylene radical: R c R 2 or 2) Y 3 represents a radical of general formula II and each of the pairs (Y 1 , Y 2) and (Y 4, Y 5) represents an optionally substituted methylene radical, or 3) Y 5 represents a radical of formula II and each of the pairs (Y 1, Y 2) and (Y 3, Y 4) represents a radical

  optionally substituted methylene.

  The compounds according to the invention exist in the form of optical isomers and optionally also in the form of geometric isomers. The various isomers,

  as well as their mixtures, are also part of the

  this invention. The compounds according to the invention can be applied alone, mixed with one another or mixed with other active substances. It is optionally possible to add thereto, depending on the purpose that is in view, defoliants and products for protection. plants or agents

  When it is desired to extend their field of

  addition to other biocides, including

  Herbicides chosen among the active ingredients which are cited in Weed Abstracts, Volume 31, N 7, 1982, under the title "List of common names and abbreviations employed for currently used herbicides and plant growth regulators".

Weed Abstracts ".

  It is good to apply the active ingredients according to the invention, or mixtures thereof, in the form

  compositions, such as powders, spreading agents,

  Nules, solutions, emulsions or suspensions, containing

  liquid and / or solid carriers or diluents and

  wetting agents, adhesives, emulsifiers and / or dispersants, preferably in the form of concentrates:

emulsifiable -

  Suitable liquid carriers include

  for example, water, aliphatic or aromatic hydrocarbons

  such as benzene, toluene and xylenes,

  cyclohexanone, isophorone, dimethylsulfoxide, dimethyl

  thylformamide, as well as mineral oil fractions.

  The solid supports will for example be mineral soils, such as Tonsil, silica gel, talc, kaolin, Attaclay, limestone and silica,

  or plant products, such as flours.

  As surfactants, for example, the

  Calcium lignin sulphonate, polyethoxy

  alkyl phenols, naphthalene sulfonic acids and salts thereof, phenol sulfonic acids and salts thereof, formaldehyde condensation products, fatty alcohol sulfates and substituted benzenesulphonic acids and salts thereof. The proportion of the active ingredient (s)

  in the various formulations may vary

  In this way, products will be able to

  for example, from about 5 to 95% by weight of active materials, from about 95 to 5% by weight of liquid or solid carriers and, optionally, up to 20% by weight of surfactants. The spreading of the products can be done in the usual way, for example with water as a carrier in the form of slurries that are sprayed at doses of about 100 to 1000 liters per hectare. It is also possible to apply the products by the so-called "low volume" process and the so-called "very low volume" process, as well as

  only in the form of microgranules.

  To prepare the formulations we will use

example the following constituents.

A Wettable powders.

  a) 40% by weight of active ingredient,% by weight of clay minerals, 20% by weight of colloidal silica,% by weight of pitch from the treatment of cellulose and% by weight of surfactants based on a mixture of salt calcium from lignin-sulfonic acid and polyethoxylation products from alkylphenols; b) 25% by weight of active ingredient,% by weight of kaolin,% by weight of colloidal silica and 5% by weight of surfactants based on the sodium salt of N-methyl-N-oleyl-taurine and the calcium salt of lignin-sulfonic acid; c) 10% by weight of active ingredient,% by weight of clay minerals,% by weight of colloidal silica,% by weight of cellulosic pitch and 5% by weight of surfactants based on the sodium salt of N-methyl-N -oleyl-taurine and calcium salt

lignin-sulfonic acid.

B Paste.

  45% by weight of active material,% by weight of a sodium alumino-silicate,% by weight of a cetylpolyglycolic ether with 8 moles of ethylene oxide, 2% by weight of a pin oil, 10% by weight of a polyethylene glycol and

23% by weight of water -

C Emulsifiable concentrates.

  a) 25% by weight of active ingredient,% by weight of cyclohexanone, 55% by weight of xylene and% by weight of a mixture of a product of poly-

  ethoxylation of nonylphenol and dodecylbenzene

calcium sulfonate.

  b) 10% by weight of active material, 6% by weight of cyclohexanone, 36% by weight of xylene,

  12% by weight of a mixture of a polyethoxylated product

  tion of nonylphenol and dodecylbenzene

  calcium sulphonate and 36% by weight of a paraffin-rich mineral oil.

  To prepare the compounds according to the invention

  For example, it is possible to: a) react compounds of the general formula II

CH 2 O Y '

i 2

CH O Y'2

CH O Y 3

CH O Y'4

CH 2

CH Y Y, 5

  in which one of the symbols Y 'represents hydrogen and each of the couples that can be formed with the other symbols Y' represents a radical R 1 c / R with compounds of general formula III

U C 0-X

2 o

CF 3 _ X _ O Z (III)

  optionally in the presence of acid acceptors and / or a catalyst, or b) reacting compounds of the general formula IV

CH O ''

H - O Y '' -

 H 2

CH-O, O Y '3 (IV)

CH Y ''

  In which one of the substituents Y "represents a radical Co -

HO OD Z

  and each of the pairs which can be formed with the other substituents Y "represents a radical a radical: ## STR2 ## with compounds of the general formula V u CF 3 y

0 3O (V)

W

  in the presence of acid acceptors and / or a catalyst, formulas in which R 1, R 2, Z, U and W have the meanings previously given, and X represents a halogen atom, preferably chlorine or bromine

  The reaction is carried out at a temperature

  ture between -10 and 1500 C, but generally between room temperature and the reflux temperature of the reaction mixture The reaction time can range from 1 to 72 hours is usually under normal pressure or under a slight overpressure The reaction partners The reaction media which are suitable are, in particular, solvents which are inert with respect to the reactants which are part of the reaction.

  suspension are chosen according to the halides of

  corresponding kyles or acyls and according to the accept-

  The solvents or mediums of sus-

  for example, aliphatic or aromatic hydrocarbons, such as petroleum ether, cyclohexane, hexane, heptane, benzene, toluene and xylenes; halogenated hydrocarbons such as methylene chloride, ethylene chloride, chlorobenzene, chloroform, carbon tetrachloride and tetrachlorethylene; of the

  ethers, such as diethyl ether, diisopropyl ether,

  pyle, anisole, dioxane and tetrahydrofuran; carbonitriles, such as acetonitrile and propionitrile;

  carboxamides, such as dimethylformamide; the dim

  sulfoxide; ketones, such as acetone, di-

  ethyl ketone and methyl ethyl ketone; alcohols, such as methanol, ethanol, propanol and butanol,

  as well as mixtures of these solvents with each other

  in some cases a reaction partner can itself serve as a solvent. Acid acceptors may be

  organic bases, such as triethylamine, trimethyl-

  amine, N, N-dimethylaniline, pyridine and bases

  pyridines (4-dimethylaminopyridine), or inorganic bases

  such as oxides, hydroxides, carbonates,

  alkali metal hydrogencarbonates and alkoxides

  alkaline earth metals, as well as alkali metal salts of carboxylic acids (KOH, NaOH, Na 2 C O 3,

CH 2 COO Na).

  Bases that are liquid, such as

  pyridine can be used as solvents at the same time.

  Hydrogen genide that forms can also, in many cases, be removed from the reaction mixture by passage of an inert gas, such as nitrogen, or be absorbed by

a molecular sieve.

  It may be advantageous to operate in the presence of a catalyst. Suitable catalysts include, for example, potassium iodide and onium compounds, such as ammonium compounds, phosphonium compounds, and the like.

  and quaternary arsoniums as well as sulpho

  Also suitable are polyglycol ethers, more particularly cyclic ethers, for example

2535719

  18-crown-6 ether, and tertiary amines, such as

  latributylamine Ammonium compounds are preferred.

  quaternary compounds, such as benzyl triethyl

  ammonium and tetrabutyl ammonium bromide.

  The compounds according to the invention which have been prepared as indicated above can also be

  isolated from the reaction mixture by the usual methods

  tual; for example, the solvent used will be removed by distillation under normal pressure or under reduced pressure, or precipitation by water or extraction will be used.

  to achieve a high degree of purity by performing a chroma-

  columnography or fractional distillation.

  The compounds according to the invention

  usually in the form of almost

  odorless, sometimes in the form of

  tallies, which dissolve poorly in water, which dissolves

  under certain conditions in aliphatic hydrocarbons

  ticks, such as petroleum ether, hexane, pentane

  and cyclohexane, and dissolve well in hydrocarbons.

  halogenated bures, such as chloroform,

  methylene and carbon tetrachloride in hydro-

  aromatic carbides, such as benzene, toluene and

  xylenes, in ethers, such as diethyloxide, tetra-

  Ydrofuran and dioxane, in carbonitriles, such as acetonitrile, in ketones, such as acetone, in

  alcohols, such as methanol and ethanol, in

  boxamides, such as dimethylformamide, and in sulfox-

such as dimethylsulfoxide.

  The starting corps necessary for the pre-

  paration of the compounds according to the invention are known

  or can be prepared by known methods.

  The following examples illustrate the preparation

  tion of the pentitol esters according to the invention.

EXAMPLE:

  O-L (2-chloro-4-trifluoromethylphenoxy) -5

  2-nitro benzoyl / -5 bis-O- (isopropylidene) -

1,2: 3,4 xylitol.

  We first introduce into the container

  reaction, 40.0 g (0.172 mol) of bis-O- (isopropylidene) -

  1,2,4,4-xylitol and 250 ml of methylene chloride, then 17.3 g (0.172 mol) of triethylamine are added at 20 ° C. to this mixture. The mixture is then added dropwise to this mixture at 20.degree. cooling with ice, a solution of 65.3 g (0.172 mol) of chloride (2-chloro-trifluoromethyl-4-phenoxy) -5-nitrobenzoyl in 100 ml of methylene chloride This is stirred for a further 1 hour to the ambient temperature, and then the reaction mixture is washed

  three times each time with 250 ml of water after

  the phase of methylene chloride on

  Gnesium is filtered and the solvent is removed.

  the remaining oil with 500 ml of hot hexane, then

  Once again the hexane phase is again obtained an oil, which is dried at 50 C under 0.1 mbar This oil then crystallizes little by little 61.2 g of the product is collected,

  62.4% of the theoretical quantity.

Melting point: 100.degree.

  TLC (thin layer chromatography) with a mixture of toluene and acetate as eluent

ethyl (1: 1): Rf = 0.61.

  Analysis: Calculated C 52.13% H 4.37% N 2.43% CI 6.15%

  Found C 52.28% H 4.27% N 2.66% CI 6.49%.

  The other compounds in accordance with the invention which are mentioned in

following table.

  Constant Name of the physical compound OL 2-chloro-4-trifluoromethylphenoxy) 5-nitro-2-benzoyl-1-bis-0-isopropylidene-2,3,4,5-terbitol D 0-L 4-chloro-4-trifluoromethyl-phenoxy-5-nitro- 2 benzoyl / -3 bis-O-isopropylidene-1,2,4,5 adonitol O-L (2-chloro-4-trifluoromethylphenoxy) -5-nitro-benzoyl / 5

bis-O (chloro-4-phenyl) -methyl

1,2-lene: 3,4 xylitol

  0-L Tchloro 2-trifluoromethyl-4-phenoxy) -5-nitro-2-benzoyl / -5

bis-O (chloromethyl-methyl) -

  1,2: 3,4 xylitol O-L (2-chloro-4-trifluoroxiethylphenoxy) -5-nitrobenzoyl 11 / -5

bis-O-methyl-octyl-methylene)

  1,2: 3,4 xylitol O-L 2-chloro-4-trifluoromethylphenoxy) -5-nitro-benzoyl / -5

  bis-O (ethyl-methyl-methylene)

  1,2: 3,4 xylitol O-L Chlo-ro 2 trifluoromethyl-4-phenoxy) -5-nitro-benzoyl / -5

bis-O (diethyl methylene)

  1,2: 3,4 xylitol O-L 2-chloro-4-trifluoromethylphenoxy) -5-nitro-benzoyl / -5

bis-O (methyl-methylene) -

  1,2: 3,4 xylitol n D 20 = 1,5067 n D 20 = 1.5040

F: 1730C

  n D 20 = 1.5309 D 2 n D 2 = 1.4998 n D O = 1.5191 n '20 D

1.5123

Mp 66-67 ° C

  The following examples illustrate the possibilities of application of the compounds according to the invention, which are used in the form of compositions such as

  those which have been described above.

No of -

for example

ple

6

EXAMPLE 10

  In the greenhouse, the compounds according to the invention, which are mentioned in the table, are sprayed on the test plants, in this case Viola and Matricaria, in pre-emergence and post-emergence, at the dose of 3.0 kg of active ingredient per hectare in emulsion in 500 liters of water per hectare Three weeks after treatment, the results of

  using the following rating scale:

vante: 0 = no action and

4 = destruction of plants.

  As can be seen on the table, the destruction of plants subjected to

test.

  Compound according to Pre-emergence Post-levee

  the invention Viola Matri Viola Matri

  Caria caria OL (2-chloro-4-trifluoromethylphenoxy) -5-nitro-2-benzoyl-5-bis-O- (isopropylidene) -1,2: 3,4-xylitol OL (2-chloro-4-trifluoromethylphenoxy) -5-nitro 2-benzoyl / -1 bis-O-isopropylidene-2,3,4,5-dibenzol-1-bis (2-chloro-4-trifluoromethylphenoxy) -benzoyl-1,3-isopropylidene-1,2,4,4-dibenzothiazide; 5 adonitol O - / (2-chloro-4-trifluoromethylphenoxy) 5-nitro-2-benzoyl / -5

bis-O- (4-chlorophenyl) -methyl

1,2-lene: 3,4 xylitol

4 4 4

4 4 4 4

4 4 4 4

4 4 4

14 -2535719

  Compound according to Pre-emergence Post-emergence the invention

  the invention Viola Matri Viola Matri

  Carla caria OL (2-chloro-4-trifluoromethyl-phenoxy) -5-nitro-2-benzoyl / -5-bis-O- (chloromethyl-methylene) 4 4 4 4 1,2,4,4-xylitol 4 4 4 O - / ( chloro2-trifluoromethyl-4-phenoxy-5-nitro-benzoyl / -5

bis-O- (methyl-octyl-methylene) -

  1,2: 3,4 xylitol 4,4-O 4-chloro-2-trifluoromethyl-4-phenoxy-5-nitro-benzoyl / -5

bis-O- (ethyl-methyl-methylene) -

  1,2: 3,4 xylitol 4,4-O 4-chloro-2-trifluoromethyl-4-phenoxy-5-nitro-benzoyl / -5

* Bis-O- (diethyl-methylene) -

  1,2: 3,4 xylitol 4,4-O 4-chloro-2-trifluoromethyl-4-phenoxy-5-nitro-benzoyl / -5

bis-O- (methyl-methylene) -

1,2: 3,4 xylitol 4 4 4 4

EXAMPLE 11

  In the greenhouse, the indicated plants are treated, after emergence, with the compounds mentioned, at a dose of 0.1 kg of active ingredient per hectare.

  is in the form of an emulsion which is sprayed regularly

  on plants with 500 liters of water per hectare.

  Three weeks after treatment, we find that

  posed according to the invention have not only a great

  selectivity but still an excellent activity against

weeds.

  Compound according to P 0) -P the invention P 4 O-4 H 0 ee fz O 4, -JN% a) tn cd 0 -H a) nd O Cd Q -, i1-4 4O 4> Pl MO 04 4

0 - / (2-chloro trifluoro-

4-methylphenoxy) -5-nitro-

  2 benzoyl / 5 bis-O (iso propyl) diene -1,2: 3,4 O O O O O O O O O 10 10 10 10 10 10 xylitol

0-ú- (2-chloro trifluoro-

4-methylphenoxy) -5-nitro-

2 benzoyl / -5 bis-O- (methyl-.

  O Ct Y 17 Methylene) -1,2: 3,4 O O O O O O O O O O O O O O O 10 10 10 10 10 xylitol ui Ln LM 1 t A 4,% O

Claims (11)

25357 19   1. 5-Phenoxy benzoyl derivatives of pentitols corresponding to the general formula I CH -0-Y 1 CH -O-Y 2 Cl H -0-Y 2 I% lu (-y 3 CH -0-Y 3 CH -O-Y% H 2-0 -Y   In which one of the substituents radical: -   ICO W (I) Y represents a z (II) and the couples that can be formed each time with the other substituents Y each represent a radical \ C / R 1   R 2 o: R 1 and R 2 each represent, independently of one another, hydrogen, a C 1 -C 10 alkyl radical optionally carrying one or more substituents taken from the group consisting of halogen, C 1 -C 6 alkoxy, phenoxy and radicals   halo-phenoxy, an aryl- (C 1 -C 3) alkyl radical   optionally substituted with one or more substituents taken from the group consisting of C 1 -C 6 alkyls, halogens,   C 1 -C 6 alkoxy, nitro nitric acid and radi-   trifluoromethyl cal, a hydrocarbon radical   cycloaliphatic C 3 -C 8, or a hydrophilic radical   aromatic carbonaceous material optionally bearing one or more substituents taken from the group consisting of C 1 -C 6 alkyls, halogens, C 1 -C 6 alkoxy, nitro radical and trifluoromethyl radical, or together with the carbon atom carrying them a C 3 -C 8 cycloaliphatic hydrocarbon radical, Z represents a nitro or cyano radical or a halogen atom, U represents a hydrogen or halogen atom and W represents a hydrogen or halogen atom, a cyano or trifluoromethyl radical or a C 1 -C 4 alkyl radical. 2. 5-Phenoxy benzoyl derivatives of pentitols according to claim 1, in which R 1 and R 2 each independently represent from one another, a hydrogen atom or a methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, 2,2-dimethyl radical   propyl, n-pentyl, n-heptyl, n-octyl, n-decyl, chloro   methyl, bromomethyl, fluoromethyl, dichloromethyl,   trifluoromethyl, trichloromethyl, methoxymethyl, ethoxy-   methyl, phenoxymethyl, 4-chlorophenoxymethyl, chlorinated   thyl, bromethyl, 2-ethoxyethyl, 2-phenoxyethyl, cyclohexyl,   propyl, cyclopentyl, cyclohexyl, benzyl, phenyl-2   ethyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl   Nyl, 3,4-dichlorophenyl, 4-methoxyphenyl, 4-nitro phenyl or 2,4-dichlorophenyl.   3 Phenoxy-5 benzoyl derivative of   pentitol according to one of claims 1 and 2, taken in   the group consisting of: O-L (2-chloro-4-trifluoromethyl)   phenoxy) -5-nitro-benzoyl / -5 bis-O- (isopropylidene) -1,2: 3,4 xylitol 18 2535719   2-chloro-2-trifluoromethyl-4-phenoxy-5-nitro-2-benzoyl-1,3-bis-isopropylidene-2,3,4,5-tert-arbitol O-, CT 2-chloro-4-trifluoromethyl-phenoxy) -5 2-nitro-benzoyl-3-bis-O-1,2-isopropylidene: 4,5 adonitol 1-O- (2-chloro-4-trifluoromethyl-phenoxy) -5-nitro-benzoyl 11 / -5 bis-O (4-chlorophenyl) -methyl   1,2-lettone: 3,4 xylitol 1 '- (2-chloro-4-trifluoromethylphenoxy) -5-nitro-2-benzoyl-5 bis-O (chloromethyl-methylene) -   1,2: 3,4 xylitol 1 'O - / (2-chloro-4-trifluoroethyl-phenoxy) -5-nitro-2-benzoyl 11 / -5 bis-O (methyl-octyl-methylene) -   1,2: 3,4 xylitol 11'-L (2-chloro-4-trifluoromethylphenoxy) -5-nitro-benzoyl / -5   bis-O (ethyl-methyl-methylene) - 1,2: 3,4 xylitol 1 '- / <chloro-2 trifluoromethyl Xl- phenoxy) -5-nitro-2 benzoyl / -5 bis-O (diethyl methylene)   1.2: -3.4 X Ylitol and O-L <2-chloro-4-trifluoromethyl-phenoxy) -5-nitro-2-benzoyl 17 bis-O (methyl-methylene) - 1,2: 3,4 xylitol.   4. Process for preparing 5-phenoxy derivatives   benzoyl pentitols according to any one of the   1 to 3, characterized in that it is   compounds of general formula II CH,) O Y eyelash O * Y, 2 I Y, 2 Y Y 5   in which one of the symbols Y 'represents hydrogen   and the couples that can be formed with the other symbols   the Y 'each represent a radical: X / R 1   R 1 with compounds of general formula III: U CO X I 3 I (III)   formulas in which R 1, R 2, Z, U and W have the meanings   cations which have been given in claim 1 and X represents   a halogen atom, preferably chlorine or bromine, optionally in the presence of acid acceptors and / or a catalyst.   5. Process for the preparation of 5-phenoxy benzpoyl derivatives of pentitols according to any one of   Claims 1 to 3, characterized in that   reacting compounds of the general formula IV: CH O Y 1 ' 12 I CH O Y '' 1 1 '2 CH o Y '' CH O Y '' 1 I U 2V 4 CH O Y 4 C 2 O -Y''5   (IV) in which one of the substituents Co-Ho, O z and the pairs which can be formed as stituents Y "each represent a XC R 1 1 c 1 R 2 Y "represents a radical with the other sub-   radical: with compounds corresponding to the general formula V: U CF 3O X (V) j w   formulas in which Z, R 1, R 2, U and W have the significances   tions which have been given in claim 1 and X represents   a halogen atom, preferably chlorine or bromine,   in the presence of acid acceptors and / or a catalyst.   6. Product with herbicidal action, characterized   in that it contains at least one compound according to any one conque of claims 1 to 3.   7 Product with herbicidal action according to the   6, characterized in that it also contains supports and / or adjuvants.   8. Product with herbicidal action according to the   6, characterized in that it contains a compound   which has been prepared according to one of claims 4 and 5.