CA1202032A - Phenoxypropionylphosphonic acid esters - Google Patents

Phenoxypropionylphosphonic acid esters

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Publication number
CA1202032A
CA1202032A CA000465249A CA465249A CA1202032A CA 1202032 A CA1202032 A CA 1202032A CA 000465249 A CA000465249 A CA 000465249A CA 465249 A CA465249 A CA 465249A CA 1202032 A CA1202032 A CA 1202032A
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Prior art keywords
phenoxy
compound
formula
phosphonate
propionyl
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CA000465249A
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French (fr)
Inventor
Theodor Pfister
Ludwig Eue
Robert R. Schmidt
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Bayer AG
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Bayer AG
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4062—Esters of acids containing the structure -C(=X)-P(=X)(XR)2 or NC-P(=X)(XR)2, (X = O, S, Se)
    • C07F9/4065—Esters of acids containing the structure -C(=X)-P(=X)(XR)2, (X = O, S, Se)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/58—Pyridine rings

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Biochemistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

ABSTRACT OF THE DISCLOSURE

There are disclosed and claimed new phenoxypropionyl-phosphonic acid esters, a process for the preparation thereof and the use of such esters as herbicides.

Description

~Z~3203Z

231 89- 583r) The invention relates to new phenoxypropionyl-phosphonic ac;d esters, a process for their preparat;on and the;r use as herbicides.
It has been disclosed that a large number of phenoxypropion;c ac;d der;vatives possess herb;c1dal pro-pert;es (see, for example, DE-OS (6ernan Published Speci-fication) 2,223,894). Thus, for example, methyl 2-C4-(~,4-dichlorophenoxy)-phenoxy~ propionate can be employed for combat;ng weeds~ However, the action of th;s sub-stance ;s not al~ays adequate, part;cularly where small amounts are used.
New phenoxyprop;onylphosphonic ac;d esters of the formula (I) x2 ~ ~)- O - C H - C - P ( O R ) 2 ( I ) ;n ~hich x1 represents halogen or ~rifluoromethyl, x2 represents hydrogen, halogen or tr;fluoro-methyl, Z represents nitrogen or a -CH or CCl-grouping and R represents alkyl or halogenoalkyl, have no~ been found.
~he new phenoxyprop;onylphosphonic ac;d esters of the for~ula (I) exist ;n tautomer;c equ;librium ~;th compounds of the formula (la):
x2 O - C H - e - ~ ( o R ) 2 ~ ~ ) Le A 22 409 3~

O~H O

Furthermore, ;t has been found that the new phe-noxyprop;onylphosphon;c ac;d esters of the formuLa tI~
are obta;ned ;f phenoxyprop;onyl chlor;des of the formula t I I ) x2 CH3 x1 ~_o~3-0-l~H-COC ~ (II ) ;n ~h;ch X1~ x2 and Z have the meanings g;ven above, are reacted ~;th phosphorous ac;d esters of the formula ~III) P(OR)3 tIII) ;n ~hich R has the meaning g;ven above, if appropr;ate ;n the presence of d;luents.
F;nally, it has been found that the new phenoxy-propiony~phosphon;c ac;d esters of the formula tI) ared;stingu;shed by outstand;ng herb;c;dal act;v;ty.
Surpr;s;ngly~ the phenoxyprop;onylphosphon;c ac;d esters accord;ng to the ;nvention, of the formula (I), possess substant;ally better herb;c;dal propert;es than methyl 2-t4-(2,4-d;chlorophenoxy)-phenoxy~=prop;onateD
~h;ch ;s kno~n from the pr;or art and ;s a h;ghly effec-tive act;ve compound hav;ng the same mode of act;on.
Formula tI) g;ves ;n an unamb;guous def;n;t;on of the phenoxyprop;onylphosphonic ac;d esters accord;ng to the ;nvent;on. In th;s formula, X1 preferably repre-sents chlorine or tr;fluoromethyl. x2 preferably repre-sents hydrogen, chlorine or trifluoromethyl. Z prefer-ably represents n;trogen or a -CH or ~CCl grouping, and R preferably represents alkyl having 1 to 4 car~on atoms Le A Z2 409 or halogenoalkyl hav;ng 1 to 4 carbon atoms and 1 to 5 halogen atomsO ;n particular chlorine atoms.
If 2-C4-~3,5-d;chloro-pyr;d;n-2-yLoxy)-phenoxy~-prop;onyl chlor;de and tr;ethyl phosphite are used as start;ng materials, the course of the process according to the ;nvention can be represented by the follo~ing equat;on:
/Cl CH3 Cl ~ -O ~ o-CH-COCl ~ P(OC2H5~3 Cl CH3 O
Cl ~ O ~ O-CH-cO-P(oc2H5)2 Formula (Il) g;ves a def;n;t;on of the phenoxy-prop;onyl chlor;des required as start;ng materials in the process accord;ng to the ;nvent;on. In th;s formula~ X', x2 and Z preferably have those mean;ngs wh;ch have al-ready been ment;oned ;n connect;on ~;th the descr;ption of the substances accord;ng to the ;nvent;on, of the for-mula (I), as being preferred for these radicals.
The follo~;ng may be mentioned ;nd;v;dually as examples of compounds of the formula (II):
2-C4-~4-trifluoromethyl-phenoxy)-phenoxy~-, 2-C4-(2,4-d;-chlorophenoxy)-phenoxy~-, 2-C4-~4-chloro-2 trifluoro-methyL-phenoxy)-phenoxy~-, 2-C4-t2,6-d;chloro-4-tr;fluoro-2û me~hyl-phenoxy)-phenoxy~-, 2-~4-(2-chloro-4-tr;fluoro-methyl-phenoxy)-phenoxy~-, 2-C4-(3,5-d;chloro-pyr;d-2-yloxy)-phenoxy~-, 2-C4-~3-chloro-5-trifluoromethyl-pyrid-2-yloxy)-phenoxy~- and 2-C4-~S-tr;fluoromethyl-pyrid-2-yloxy)-phenoxy]-propionyl chloride.
The compounds of the formula (II) are knoun, or can be obta;ned ;n a knoun manner by react;ng the corre-spond;ng ph~noxypropion;c ac;ds of the ~ormula (IV) x1 ~ 2 O-CH-COOH (IY) Le A 22 409
3~

in ~hich X1, XZ and Z have the meanings given above, ~;th chlor;nat;ng agents, such as, for example, th;onyl chloride, ;f appropr;ate ;n the presence of ;nert diluents, such as, for example, tetrachloromethane, and, if appropriate, us;ng catalysts, such as, for example, dimethylformamide, at temperatures between 20~ and 80C
(see German Offenlegungsschriften (German Published Spec;-fications) 2,223,894, 2,433,067, 2,546,251, 2,646,124, 2,~28,384 and 2,802,818 and Ewropean Offenlegungsschrif-ten (European Publ;shed Spec;ficat;ons) 483 and 1,473~.
The phenoxyprop;on;c ac;ds of the formula (IV) uhich are required as starting mater;als for the prepara-t;on of the phenoxypropionyl chlor;des of the formula (II) are knoun.
Formula (III) gives a def;nition of the phospho-rous ac;d esters furthermore required as starting mate-rials in the process according to the invention. In this ~ormula, R preferably has those meanings uhich have al-ready been mentioned in connection hith the descriptionof the substances according to the inventior,, o~ the for mula (I), as be;ng preferred.
The following may be mentioned ;ndividually as examples of the compounds of the formula (III): tri-methyl, triethyl, tri-n-propyl, tr;-;so-propyl, tri-n-butyl, tri-i-butyl, tr;-(Z-chloroethyl)~ tri-(1-chloro-n-propyl), tr;-(2-chloro-n-propyl), tr;-(3-chloro-n-pro-pyl), tr;-(2-chloro-n-butyl), tri-(3-chloro-n~butyl) and tr;~(4-chloro-n-butyl) phosph;te.
The phosphoro~ acid esters of the formula ~III) are known ~see Houben-Weyl "Methoden der organischen Chemie" ~Methods of organic chem;stry), volume 12/2, pages ~3-78, Th;eme-Verlag Stuttgart, 196~).
The process~ accord;ng to the ;nvent;onO ~or the preparat;on of the new phenoxyprop;onylphosphon;c ac;d esters of the formula ~I) ;s preferably carr;ed out using Le A 22 409 3~

d;luents. Su;table d;luents are v;rtualLy all inert or-gan;c solvents~ These pre~erably include aromatis hydro-carbons, such as, for example, benzene, toluene and xy-lene, and ethers, such as, for example, d;ethyl ether and d;;sopropyl ether, tetrahydrofuran, d;oxane and 1,2-d;-methoxyethane.
In the process accord;ng to the invent;on, for the preparation of the new compounds of the formula tl), the reaction temperature can he var;ed ~;th;n a rela-t;vely wide range. In general, the reaction ;s carriedout ;n each case at temperatures bet~een -20C and +150C, preferably bet~een ~C and ~100C. The process accor-ding to the invent;on ;s carried out ;n general under at-mospher;c pressure.
To carry out the process accord;ng to the ;nven-t;on, ;n general between 0.5 and 2.0 mol~ preferably bet-~een 0.9 and 1.5 mol, of the phosphorous ac;d ester of the formula (III3 are employed per mol of the compound o~ the formula (II). The components are usually combined Z0 with slight external cooling, and the reaction mixture is st;rred unt;l the react;on ;s complete. Thereafter, volat;le components are dist;lled off under reduced pres-sure, the products of the formula (I) rema;ning beh;nd as a res;due. Purif;cat;on can be ach;eved by heating for a short time under reduced pressure (";ncip1ent dis-t;llat;on").
The active compounds according to the invention can be used as defoLiants, des;ccants and agents for des-troy;ng broad-leaved plants, and especiaLLy as weed-kiLlers. ~y ueeds, in the broadest sense, there are to be under~tood all plants ~hich gro~ in locat;ons ~here they are undes;red. ~hether the substances accord;ng to the ;nvent;on act as totaL or seLect;ve herb;c;des de-pends essentially on the amount used.
The active compounds according to the invention can be used, for example, ;n connection with the foLLowing Le A 22 409 ~ 6 --plants:
D;cotyledon ~eeds of the genera: S;nap;s, Lep;d;um, Ga-lium, Stellaria, Matricaria, Anthemis, GaLinsoga, Cheno-podium, Urtica, Senec;o, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesban;a, Ambrosia, Cir-sium, Carduus, Sonchus, Solanum, Rorippa, Rotala, linder-nia, Lamium, Veronica, Abutilon, Emex, Datura, ~iola, Galeopsis, Papaver and Centaurea.
Dicotyledon cultures of the genera: Gossyp;um, Glyc;ne, ~eta, Daucus, PhaseoLus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana~ Lycopersicon, Arachis, Brass;ca, Lac-tuca, Cucum;s and Cucurb;ta.
Monocotyledon weeds of the genera: Ech;nochloa, Setar;a,Pan;cum, D;g;tar;a, Phleum, Poa, Festuca, Eleus;ne, Bra-ch;ar;a, Lol;um, Bromus, Avena, Cyperus, Sorghum, Agropy-ron, Cynodon, Monochor;a, F;mbr;styl;s, Sag;ttar;a, Eleo-char;s, Sc;rpus, Paspalum, Ischaemum, Sphenoclea, Dac~yl-octen;um, Agrost;s, Alopecurus and Apera.
Monocotyledon cultures of the genera: Oryza, Zea, Triti-cum~ Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.
Ho~ever, the use of the active compounds accor~
d;ng to the ;nvent;on ;s ;n no ~ay restr;cted to these genera, but also extends in the same manner to other plants.
The compounds are su;table, depend;ng on the con-centrat;on, for the total combat;ng of weeds~ for example on ;ndustrial terrain and ra;l tracks, and on paths and squares ~ith or ~ithout tree plant;ngs~ Equally, the compounds can be employed for combating ~eeds in perenn;al cultures, for example afforestat;ons, decorat;ve tree plant;ngs~ orchards, v;neyards, c;trus groves, nut or-chards, banana plantations~ coffe plantations, tea plan-tations, rubber plantations, oil palm plantations, cocoa plantat;ons, soft fru;t plant;ngs and hopfields, and for the select;ve combating of weeds ;n annual cultures~
Le A 22 409 The active compounds accord;ng to the invent;on can be employed, by the pre-emergence and post-emergence methods, for select;vely combat;n0 grasses ;n crops such as, for example, beet, cotton, soya beans, potatoes and cereals~
The act;ve compounds can be converted to the cus-tomary formulat;ons, such as solut;ons, emuls;ons, wet-table powders, suspens;ons, po~ders, dust;ng agents, pastes, soluble powders~ granules, suspens;on-emuls;on concentrates, natural and synthet;c mater;als impregnated ~ith act;ve compound, and very f;ne capsules ;n polymer;c substances~
These formulations are produced in known manner~
for examp~e by mixing the active compounds ~;th extenders, that ;s~ l;quid solvents and/or solid carriers, opt;on-ally ~;th the use of surface-active agents, that is, emulsifying agents and/or dispersing agents, and~or foam-form;ng agents.
In the case of the use of ~ater as an extender, organic solvents can, for example, also be used as auxiliary solventsD As liquid solvents, there are suit-able in the main: aromatics, such as xylene, toluene or alkyl naphthalenes, chlorinated aromat;cs or chlor;nated aliphatic hydrocarbons, such as chlorobenzenes, chloro-ethylenes or methylene chloride, aliphatic hydrocarbons,such as cyclohexane or paraffins, for example m;neral oil fractions~ mineral and vegetable oils~ alcohols, such as butanol or glycol as ~ell as their ethers and esters, ke-tones, such as acetone, methyl ethyl ketone, methyl iso-butyl ketone or cyclohexanone, strongly polar solvents~such as dimethylformam;de and d;methylsulphox;de~ as well as ~ater.
As solid carr;ers there are su;table: for example ammon;um salts and ground natural ~inerals, such as ~aolins, clays, talc, chalk, quartz, attapulgite, montnorillonite or d;atomaceous earth, and 0round Le A 22 409 synthetic m;nerals, such as hi0hly-dispersed silicic acid, alumina and silicates as sol;d carr;ers for ara-nules there are su;table: for example crushed and frac-tionated natural rocks such as calc;te, marble, pum;ce, sepiolite and dolomite~ as uell as synthetic granules of ;norganic and organ;c mea~s, and granules of organic ma-ter;al such as sawdust, coconut shells, ma;ze cobs and tobacco stalks; as emuls;fy;ng and/or foam-form;ng agents there are suitable: for example non-;on;c and anionic emulsifiers, such as polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, for example alkyl-aryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates as ~ell as albumin hydrolysation pro-ducts; as d;spersing agents there are su;table: for example l;gn;nsulphite waste liquors and methylcellulose.
Adhesives such as carboxymethycellulose and natu-ral and synthet;c polymers ;n the form of powders, gra-nules or lat;ces, such as gum arab;c~ polyv;nyl alcohol and polyv;nyl acetate, as ~ell as natural phosphol;p;ds, 2û such as cephal;ns and lec;th;ns, and synthetic phospholi-p;ds, can be used ;n the formulat;ons. Further add;t;ves can be mineral and vegetable o;ls.
It ;s poss;ble to use colorants such as inorganic pigments, for example iron ox;de, t;tanium oxide and Pruss;an Blue, and organ;c dyestuffs, such as al;zar;n dyestuffs, azo dyestuffs and metal phthalocyan;ne dye-stuffs, and trace nutrients such as salts of ;ron, manga nese, boron, copper, cobalt, molybdenum and zinc.
The formulat;ons ;n general contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90X.
The active compounds according to the ;nvention, as such or in the form of their formulations, can also be used, for combating u~eds, as mixtures w;th known her-b;c;des, fin;shed formulat;ons or tank m;xing be;ng pos-s;ble.
Le ~ 22 409 3~2 Su;table herb;cides for ~he m;xtures are known herb;c;des such as, for example, 1-am;no-6-ethylth;o-3-t2,2 dimethylpropyl~-1,2,5-tria2ine-2,4-~1H, 3H)-dione or N-t2-benzoth;azolyl)-~,N'-d;methyl-urea for combat;ng ~eeds ;n cereals, 4-amino 3 methyl-6-phenyl~1,2,4~triaz;n-5-(4H)-one for combat;ng ~eeds in sugar beet, and 4-amino-6-(1,1-di~ethyl3-3-methylth;o-1~2,4-tr;azine-5-(4H)-one for combat;ng weeds ;n soya beans. Sur-pr;s;ngly, some of the m;xtures also exh;b;t a synerg;s-t;c effect.
M;xtures ~;th other known act;ve compounds, such as fun~icides, insectic;des, acar;cides, nematic;des, b;rd repellants, plant nutrients and agents ~h;ch improve soil structure, are also poss;ble.
The active compounds can be used as such, in the form of their formulations or ;n the use forms prepared therefrom by further d;lution, such as ready-to-use solu-t;ons, suspens;ons, emuls;ons, powders and granules.
They are used ;n the customary manner, for example by ~ater;ng, spraying, atomising or scatter;ng.
The act;ve compounds accord;ng to the ;nvent;on can be applied e;ther before or after emergence of the plants.
They can aLso be ;ncorporated into the soil be-fore sow;ng.
The amount of active compound used can vary~;th;n a substant;al range. It depends essent;ally on the nature of the des;red effect. In general, the amounts used are between 0.05 and 10 kg of act;~e com-pound per ha, preferably between 0.1 and S kg/ha.
The preparat;on and the use of the substance ac-cord;ng to the ;nvent;on can be seen from the examples ~hich follow:

Le A 22 409 - 10 ~
Example 1 Cl ~ Cl 0 IH~ tOC H ~

A solution of 1~3 9 tO.0~ ~o~ of 2-~4-~3,5-d;-chloropyr;d-2-yloxy)-phenoxy~-prop;onyl chlor;de in 60 ml of diethyl ether uas added dropw;se, wh~le cool;ng ~ith ice, to a solution of 6~7 9 (0.04 ~ol) of triethyl phos-ph;te ;n ~0 ml of d;ethyl ether. The react;on mixture ~as stirred for 72 hours at 20C and then heated under reflux for 9 hours. After the mixture had been evapo-rated do~n under vacuum from a water jet, the res;dual volatile components ~ere removed at 60C/1 mm Hg.
In this manner~ 14.1 9 ~79X of theory) of d;ethyl 2-~4-~3,5-d;chloro pyrid-2~yLoxy)-phenoxy]-prop;onyl phosphonate of refractive index n2:1.5429 ~ere obtained.
The follo~;ng compounds of the formula ~I) were obta;ned analogously to Example 1:
x2 ~ ~ 0-CH-C-F'(OR)2 ~I) Example X1 X2 Z R Refract;ve ;ndex nD
No.
2 CF3 H CH CH3 1.5032 3 CF3 H CH C2H5 1.4905
4 Cl Cl N CH3 Cl Cl 3 7 6 Cl Cl 2CH2Cl 7 CF3 H N CH3 1.5043 8 CF3 Cl N CH3 9 CF3 H N C2H5 1.4909 CF3 Cl 2 5 Le A 22 409 ~2~2 PrPparation of start;ng mater;als of the formula (lI):
Çxample tII-1~

Cl~-o~ 1`
N

A ~;xture of 25.6 9 (0.07 mol) o~ 2-C4-(3,5-d;-chloropyr;d-2-yloxy)-phenoxy]-propionic acid, 26 g (0.22 mol) of thionyl chloride and one drop of dimethylformam;de ~as heated under reflux for 15 hours.
The volatile components were then removed at 60C/1 mm Hg.
In this manner, 14.3 9 (59X of theory) of 2~C4-lD (3,5-d;chloro-pyr;d-~-yloxy)-phenoxy~-prop;onyl chloride ~ere obtained.
The following compound of the formula (II) was obtained analogously to Example (II-1) Example (II-2) F3C ~ O ~ O-CH-COCl b.p. = 182~ to 185C/2 mm Hg Use example:
In the biological test descr;bed below, the fol-low;ng compound was employed as a comparative substance:

tA ) C l ~0~ C~ H 3 methyl 2-~4-(2,4-d;chLorophenoxy)-phenoxy~-prop;onate tdisclosed in DE-OS tGerman Published Specificat;on) 2,~23,894).

Le A 22 409 3~

Example A
Post-emergence ~est Solvent: 5 parts by ueight of acetone Emulsifier: 1 part by ~eight of alkylaryl polyglycol ether To produce a suitable preparat;on of act;ve com-pound, 1 part by ~eight o~ active compound is mixed uith the stated amount o~ solvent, the stated amount of emulsi-fier is added and the concentrate is diluted with uater to the des;red concentrat;on.
Test plants wh;ch have a height of 5 - 15 cm are sprayed uith the preparation of the active compound in such a vay as to apply the part;cular amounts of active compound des;red per unit area. The concentration of the spray liquor ;s so chosen that the particular amounts of active compound desired are applied ;n 2,000 l of water/ha. After three ueeks~ the degree of damage to the plants is rated ;n X damage in compar;son to the development of the untreated control~ The figures denote:
OX = no action tlike untreated control) 100X = total destruction In th;s test, active compound (1) according to the invention exhibits a better selective herbicidal act;v;ty than the comparison substance ~A) in combating A~opecurus, Digitar;a, Echinocloa9 Setaria and Sorghum ;n beet.

Le A 22 409

Claims (28)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A phenoxypropionylphosphonic acid ester of the formula (I) in which X1 represents halogen or trifluoromethyl, X2 represents hydrogen, halogen or trifluoromethyl, Z represents nitrogen or a -CH or -CC1 grouping, and R represents alkyl or halogenoalkyl.
2. A phenoxypropionylphosphonic acid ester according to claim 1 in which X1 represents chlorine or trifluoromethyl, X2 represents hydrogen, chlorine or trifluoromethyl, Z represents nitrogen or a -CH or -CC1 grouping, and R represents alkyl having 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms.
3. A phenoxypropionylphosphonic acid ester according to claim 2 wherein X1 is chlorine.
4. An ester according to claim 3 wherein X1 is CF3.
5. An ester according to claim 3 wherein Z is nitrogen.
6. An ester according to claim 4 wherein Z is nitrogen.
7. An ester according to claim 4 wherein Z is -CH.
8. An ester according to claim 3 wherein x2 is chlorine.
9. An ester according to claim 4 wherein X is chlorine.
10. Diethyl 2-[4-(3,5-dichloropyrid-2-yloxy)-phenoxy]-propionyyl-phosphonate of the formula
11. Dimethyl 2-[4-(4-trifluoromethylphenoxy)-phenoxy]-propionyl-phosphonate of the formula
12. Diethyl 2-[4-(4-trifluoromethylphenoxy)-phenoxy]-propionyl-phosphonate of the formula
13. Dimethyl 2-[4-(5-trifluoromethylpyrid-2-yloxy)-phenoxy]-propionyl-phosphonate of the formula
14. Diethyl 2-[4-(5-trifluoromethylpyrid-2-yloxy)-phenoxy]-propionyl-phosphonate of the formula
15. Di-n-propyl 2-[4-(3,5-dichloropyrid-2-yloxy)-phenoxy]-propionyl phosphonate of the formula
16. A method of combating weeds which comprises applying to the weeds or to their habitat a herbicidally effective amount of a compound according to claim 1.
17. A method according to claim 16 wherein the compound is applied in the form of a composition containing said compound as active ingredient in admixture with a suitable carrier or diluent.
18. A method according to claim 16 or 17 wherein the compound is applied as a pre-emergence herbicide.
19. A method according to claim 16 or 17 wherein the compound is applied as a post-emergence herbicide.
20. A method according to claim 16 or 17 wherein the compound is applied to an area of cultivation at a rate of between 0.05 and 10 kg/ha.
21. A method according to claim 16 or 17 wherein the compound is applied to an area of cultivation at a rate of between 0.1 and 5 kg/ha.
22. A method according to claim 16 or 17 wherein such compound is diethyl 2-[4-(3,5-dichloropyrid-2-yloxy)-phenoxy]-propionyl-phosphonate.
23. A method according to claim 16 or 17 wherein such compound is dimethyl 2- [4-(4-trifluoromethylphenoxy)-phenoxy]-propionyl-phosphonate.
24. A method according to claim 16 or 17 wherein such compound is diethyl 2- [4-(4-trifluoromethylphenoxy)-phenoxy]-propionyl-phosphonate.
25. A method according to claim 16 or 17 wherein such compound is dimethyl 2- [4-(5-trifluoromethylpyrid-2-yloxy)-phenoxy]-propionyl-phosphonate.
26. A method according to claim 16 or 17 wherein such compound is diethyl 2- [4-(5-trifluoromethylpyrid-2-yloxy)-phenoxyl-propionyl-phosphonate.
27. A method according to claim 16 or 17 wherein such compound is di-n-propyl 2-[4-(3,5-dichloropyrid-2-yloxy)-phenoxy]-propionyl-phosphonate.
28. Process for the preparation of a phenoxypropionylphosphonic acid ester of the formula (I) defined in claim 1 characterised in that a phenoxy-propionyl chloride of the formula (II) in which X1, x2 and Z have the meanings given in claim 1, is reacted with a phosphorous acid ester of the formula (III) P(OR)3 (III) in which R has the meaning given in claim 1.
CA000465249A 1983-10-15 1984-10-12 Phenoxypropionylphosphonic acid esters Expired CA1202032A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP3337540.2 1983-10-15
DE19833337540 DE3337540A1 (en) 1983-10-15 1983-10-15 PHENOXYPROPIONYLPHOSPHONIC ACID ESTER

Publications (1)

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CA1202032A true CA1202032A (en) 1986-03-18

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JP (1) JPS6097988A (en)
CA (1) CA1202032A (en)
DE (1) DE3337540A1 (en)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3664822A (en) * 1970-02-24 1972-05-23 Baychem Corp Dialkenyl esters of aryloxyacetyl phosphonic acids as herbicides
AU6651581A (en) * 1980-02-01 1981-08-06 Rhone-Poulenc, Inc. 2-nitro-(substituted phenoxy) benzoyl derivatives as herbicides
JPS5832890A (en) * 1981-08-21 1983-02-25 Sumitomo Chem Co Ltd Phosphonic ester derivative, its preparation, hebicide containing the same as active ingredient

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JPS6097988A (en) 1985-05-31
DE3337540A1 (en) 1985-04-25

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