CA1108168A - Herbicides - Google Patents

Herbicides

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Publication number
CA1108168A
CA1108168A CA285,393A CA285393A CA1108168A CA 1108168 A CA1108168 A CA 1108168A CA 285393 A CA285393 A CA 285393A CA 1108168 A CA1108168 A CA 1108168A
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Prior art keywords
formula
compound
halogen
optionally substituted
alkyl
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CA285,393A
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French (fr)
Inventor
Manfred Koch
Hermann Bieringer
Peter Langeluddeke
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Hoechst AG
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Hoechst AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/12—Radicals substituted by oxygen atoms
    • 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
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • 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
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/20—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom three- or four-membered rings
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • 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
    • 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
    • C07C69/62—Halogen-containing esters
    • C07C69/63—Halogen-containing esters of saturated acids
    • 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

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Furan Compounds (AREA)

Abstract

Abstract of the disclosure:
Compounds of the formula I

have a good herbicidal action in pre-emergence and post-emer-gence application against important weed grasses and are well tolerated by dicotyledoneous crop plants and various cereals so that the compounds are suitable for the selective control of weed grasses in agricultural crops.

Description

~ 8168 ~OE 76/F ?

This inv~ntion relates to compounds of the formula in which R1 is halogen, CF3 or C1-C4 alkyl, Z is -CN, -CS-NH2,~CO-R2 or -CH2-O-R3, R2 is hydroxy, -O-cat; C1-C~2alkoxy (optionally substituted by OH, halogen, CF3, C1-C6alkoxy, C1~C4alkylthio, phenyl, phencx~.
or halophenoxy), a radical of one of the formulae ~o7 ~ , -oc~2~
2 ~1)2-~ CmH2m~ oc2il4-N
(c~-c4)alk 2 4 __ in which -N A stands for the pyrrolidinyl, piperidinyl., mor-pholinyl~or N-methyl-piperazi.nyl radical; C5-C6cycloalkoxy (op-tionally substituted by C1-C4al]cyl, and/or haloyen), C3-C4alke-~ r,yloxy; cyclohex~-nyloxy; C3-C~alkin~loxY.. (Qptionall;v sl~bstitut~d in 1-posi.ti~ by .. ~ C1-C4alkyl and/or phenyl), phenoxy ~cptionally substituted by halogen, NO2 and/or C1-C4alkyl), C1-C6alkylth.io, allylthio, pher thi.o, halophenylthio, amino, C1-C4alkylamino, hydroxyethylamino, di-C1-C4al~sylamino, pyrrolidino, piperidino, morpholino; anilir.o (optionally substituted by halogen, C~3 and/or C1-C4alkyl~; or hydrazino, R3 is hydrogen, C1-C4alkyl~ C1-C4alkylcarbonyl, ha~o~C1-C4alkyl-' carhonyl, benzoyl (optlonal1y substituted hy halogen, NO2 an~ o^

.
' ' , -'' . ~ , 16¢~3 Cl-C4alkyl), Cl-C4alkylcarbamoyl, di-Cl-C4alkylcarbamoyl, phenylcarbamoyl ~optionally substituted by halogen and/or Cl-C3alkyl), Cl-C4alkylsulfonyl, phenylsulfonyl, -S03H or -S03cat, cat is the cation equivalent of an inorganic or organic base, n is an integer of from 1 to 3 and m is an integer of from 1 to 6, on the proviso that when Rl is 4-CF3 n being 1~ or Rl is 4-CF3 and 2-halogen, n being 2, then R2 is not hydroxy, an -O-cation group, lower alkoxy, Cl-C4 alkylthio, amino, Cl-C4 alkylamino or di-Cl-C4 alkylamino.
"cat" preferably is the cation equivalent of an inorganic base such as Na , K , 1/2 Ca and 1/2 Mg , or NH4 and cations of organic amines such as the various aliphatic mono-, di- and tri-alkylamines, the corresponding ; triethanolamines, aniline, methylaniline, benzylamine and diphenylamine.
Preferred halogens are chlorine and bromine.
If the radicals R2 or R3 contain substituted phenyl groups these may ; contain up to three and preferably one substituent; in the case of alkyl groups as substituen*s methyl or ethyl are preferred.
Preferred compounds of formula I are those in which (Rl)n represents 4-chloro, 4-trifluoromethyl or 2,4-dichloro and Z is a radical of the formula -CH2-0-R3 in which R3 has the indicated meaning.
Further preferred compounds of formula I are those in which ~Rl)n represents 4-chloro or 2,4-dichloro and Z s~ands for a radical of the formula -CO-R2 in which R2 has the indicated meaning.
Especially preferred compounds are those in which (Rl)n is 4-chloro or 2,4-dichloro, Z a radical of the formula -CO-R2 and R2 is hydroxy, -Ocat, Cl-C12alkoxy ~optionally substituted by -OH, halogen, -CF3, Cl-C6alkoxy, Cl-C4 alkylthio, phenyl,
- 3 -''~' i~

.
, 110 8~6 8 H0~ 76/E1 ~00 phenoxy, or halophenoxy), radicals of the formula -OCH2 ~ , -OCH2 ~ , -OCH2 ~ ~ -or~ -(oc2H4)2_3 - C~.H2m-1;

C5-C6cycloalkoxy (optionally substituted by C1-C4alkyl and/or halogen), C3-C4alkenyloxy, cyclohexenyloxy, C3-C~alkinyloxy (optionally substituted in 1-position by C1-C~alkyl and/or phenyl), phenoxy (optionally substituted by halogen, N02 and/or C1-C4alkyl), C1-C6alkylthio, allyl.thio, phenylthio or halophenyl-thio and m i.s an integer from 1 to 6.
The compounds of formula I can be prepared by a variety of methods.
a) The compounds I are obtained, ~or example, by reacting com ~. pounds of the formula III with compounds of the formula II, .~ according to the followin~ reactjon scheme (R)n ~ ~~ ~ C CH2CH2Z ~-~

II ~II

(R)n ~ ~ ~ -O-C~-CH2c~i2ZiHy -. I

In th~ a~oresaid ~ormulae Y is halogen, preferably bromine ,- ,1 or chlorine, or the mesylate or the tosyl.ate radical. The .. reaction is pre~erably carried out under basic conditions at a temperature in the ran~e of from 20 C to the ~oiling point of the mixture, in an inert solvent such as toluene, xylene, di-. .
methylformamide or dimethylsulfoxide. Suitable bases are al-kali met~ll or alkaline earth metal carhona-tes or hydroxides or . _ 4 ', , .
-- . - - .~ , :
:-~ , . : .
~ ':

11081~8 terti.ary organic amines such as pyridine or triethylamine.
The starting compounds of formulae II and III are known from literature and are prepared. by known methods.
b, The compounds of formula I can also be prepared by reacting compounds of formula II with an equivalent or excess amount of y-valero-lactone of formula IV under basic conditions at temperatures of from 100 C to 240 C. The reaction proceeds according to the following scheme:
( 1)n ~ -O- ~ ~ O~I + CH3 ~ base II IV

:~ (R1)n ~ --o_ ~ -ocH-c~2-c~2-cooKat ~he compounds of formula II are preferably used in the form of their alkali metal phenolates. The reactioll can be carried out in the presence or absence of a solvent.
c) The compounds oE formula I thus obtained if desired, can be transformec1 into other compounds of formula I by generally known reacti.ons, or example by saponification, e~terifica tion, salt formation, transesterification, amidation, dehy--dration, hydration, reduction, or oxidation. Thus, for in--stance, compounds containing the functional group Z = COOH
. may be transformed into acid halides by means of halogenati.ng : agents, for example SOC].2, into aMides by means of amines, into carboxylic acid salts by means of bases and into esters by means of alcohols Es.ters can also be obtained by reac-ting the corresponding acid halide with an alcohol or by alkylation of a sal.~ of the ~ 5 -:~ ' ' .
~ . .

1~0~ 8 acid, for example ~ith a halogen compound or a dialkyl sulfate.
Compounds containi.ng the functional group Z = CN can be obtained, for example, by dehydration of a primary amide (Z =
CONH2) ~ h phosphorus pentoxide, the functional group ,~S
Z = C may be obtained by the addition of hydrogen su].fide NE~2 to the nitrile group (~ = CN). Likewise the functional group Z = CONEI2 can be obtained by adding water to the nitrile group while the functional group Z = -CH2OH can be obtained, for ex-ample, by reducing an ester function by means of li.thi.um alumi-10 num hydride. All these methods are generally known and familiar to the expert.
The c~ounds cf fon~ula I of the invention exhibit a good her~icidal action m pre-emergeLlce and post-en~rgence application against numerous ~
po.rtant w2ed grasses, such as A~7ena spp. (wild oats) ~lopecurus (annual bl.ac.'~-grass), Setaria spp., Echinochloa spp., Digitaria spp., Lolium spp. and Poa sp?.; 15 On the other hand, even high doses are well tol~rated b~ dioctyledoncus crop plants and various cereals so that the co~pounds are suitable for the selective con~rol of weed grasses in agricultural crops.
The compositions of the invention contain preferahly 2 -95 % of the active compounds of the formula I. They are custo-mar1ly formulated as wettable powder~, emulsifiable concentrates, dusting agents, granules, etc.
Wettable powders are formulations which are uniformly dispersible in ~ater and wlllch, in addition to th~ active com-pound, also contai.n diluents or inert materials, wetting agents, ~5 for example, polyoxyethylated alkylphenols, polyoxyethylated -~ oleylamines or stearylamines, alky].sulfonates or alkylphenyl-sulfonates and dispersing agents, for example sodium lignin-sul-- 6 ~

i~OE -/6/F 2C0 ~0~

fonates, so~i.um 2,2'-dinaph.hyLrethane-6,6'-disulfonate or the sodium ~salt of oleyl-methyl-taurine.
Emulsifiable concentrates are obtained by dissolving the active compound in an organic solvent, for example, butanol, cyclohexane, dimethylformamide, xylene or even higher-boiling aromatics, and adding a non-ionic wetting agent, for example, a polyoxyethylated alkylphenol or a polyoxyethylated oleylamine or stearylamine.
Dusting agents are obtained by g.rinding the active com 1G pound with finely solids, for example talc, natural clays, such as kaolin, bentonite, pyrophi.llite or diatomaceous earth.
Granules can be manufactured either by spraying the ac~ive compound onto ahsorbent, granular inert material or by appylin~
active compound concentrates by means of adhesives, for examp3.e polyvinyl alcohol, sodium polyacrylate or even mineral oils, onto the surfaces of carriers, such as sand, kaolinites or gra nular inert ma~erial. Suitable formulatiorls can alsc be manu-factured by the customary methods of manufacture of fertilizer granules, if desired in admixture with fertilizexs.
In the case o~ herbicidal. a~ents, the concentrations of the acti.ve compounds in the commercial ~ormulations can vary.
In wettable po~1ders, the active compound concentration varies, for example, b~tween about ~0 % and 95 %, the remainder con-sisti.ng of one or more of the abovementioned formulation addi-^
tives. In the case of emulsifiable concentrates, the active com-pound concentration is about 10.% to 80 %. Dust formulations : usually contain 5 - 20 % of active compound, and sprayable sol.u-tions about 2 - 20 ~. In the case of granules, the actlve cor,-29 pound content in part depends on ~hether the active compound is : - 7 -' ~IOE 7~)/F 2C0 ~0~1~8 in a liquid or solid form and what granulating auxiliaries, fillers and tlle like are used.
If necessary or desired the commercial concen~rates may be diluted prior to application in the usual manner, for example by means of water in the case o~ wettable powders and emulsi-fiable concentrates. Dusts and granules are generally ready for use without further dilution. The amoun~ of active ingre-dient necessary for obtaining the desired result depends on external conditions such as temperature, humidity, type of soil, stage of p3ant development etc. It can vary within wide limits for example between 0.1 and 10.0 kg/ha of active substance but is preferably between 0.1 and 5 kg/ha.
The following examples illustrate the invention.
..
FO~1ULATION EXAMPLES

~5 E X A M P L E A:

An emulsifiable concentrate is obtained from ~- 15 parts by weiqht of active substance 75 parts by weight o~ cyclohexanone as solvent and .: .
10 parts by weight of oxethylated nonyl phel1ol (10 EO) as emulsifier.

E X A M P L E B
. _ _. . .
A wettable powder which is easily dispersible in water is ~ obtained by mixing ;~ 25 parts by weight of active substance 64 parts by weight of quartz containing kaolin as inert material ; 10 parts by weight of potassium lignosulfonate and 1 part b~ weight o~ sodium oleyl-met1lyl-taurine as wetting and dispersing agent and grinding the mixture in a pin 29 mill.

110~168 HOE 76/E 2~0 E X A M P L E C:
______ A dustlng powder is obtained by mixing 10 parts by weight of active substance and 90 parts by ~eight of talc as inert material and comminuting the mlxture in a hanmer mill.
E X _ 2~ P L E D:
A granular formul3tion consists, for example o~ about 2 to 15 parts by weight of active su~stance and 98 to 85 parts by weight of inert granular materials such as attapulgite, ~urniceand quartz sand.
EXAMPIE5 _E PREPARATION
E X A M P L E 1:
__ __
4-[4l-(2 ,4 dichloropheno~ phen~y~~_alerianic acid 20.3 g of 4-(2',4'-dichlorophenoxy~-phenol were dissclved in 25 ml of absolute ethanol. 2.1? g of meta]lic sodium ~ere added and after dissolution of the sodium the ethanol was dist~l-led off. Nextl 10 g of y-valerolactone were added to the solid 4-(2',4'-clichlorophenoxy)-phenol sodium and the whole was heated for 24 hours at 210 C. The reaction mixture was then acidified with concentrated hydrochloric acid and the residue dissolved in toluene The toluene phase was repeatedly extracted with saturated a~ueous-methanolic bicarbonate solution (50 ~ strengt.rl~.
The combined extracts were acidified with concentxated hydro-chloric acid and extracted with toluene. After xemoval of the solvent under ~educed pressure and recrystallization Lrom cyc1o-hexane~23.9 g = 80 ~ of the theory of 4-[4'-(2",4 ~dichloro-phenoxy~-pllenox~-valeric acid melting at 88 C were obtained C 1~ o ~ c~ c r~ _ C 7 ' C ~ } '~ O C ' i _ g _ , ~'' ~' ' , , ~L~081Çi8 The following com;~und~ were pr~pared in analogous manr.er:
2) ~-[4'-(4"-chloro2heno~y)-phenoxyl-valeric acid melting at 65 - 66 C.

E_A A M P L E 3:
4-[~ 4'l-dichloro~henoxy)-phenoxy]--Jaleric acid butyl ester 25.9 g of 4-(2',4'-dichlorophenoxy~-phenol and 1'l.5 g of potassium carbonate iII 150 ml of dimethyl for~amide were rerlui:-ed for 1.5 hours. 20 g of 4-chlorovaleric acid butyl ester wer2 then added dro~wise at 80 C and the mixture ~7as he~ted for 12 hours to 120 C. A~ter filtering off the precipit~ted salt, the soivent was distilled off under reduced pressure. The oily xesi-due w~s talsen up in toluene, washPd wi~h dilute sodium hydro~
~olu~ion nd water and dried~ A~ter removal of the toluene unde~-r:educPd pressure the residue was distilled in hlgh vacuum. 32.1 ~ = 78 % of the theory of 4-[4'-(2",4"-dichloropAenoxy)-phenoxy~-- valeric aci~ butylester boiling at 206 C/0.02 bar were obtained.

:,.'.'~
C~l C.~ ^-O--C'~ C~:2(~Zl2--c~
Cl \ C~2C~I2C~ CH3 Using 4-chlorovaler~nitrile t:he ~llowin~ c~.p~uncl was pre-pared in analogous manner:
4) 4-~4~-(4"-trifluoromethylpherlo~y)-phello~y] valeronitrile~
E X A M P L ~_ 5:
4 [~ (?.",4"-d~chloroph noxy)-phenox~r]-v ler~c acid n-proay-i es.e~

29 g of 4-[4~-(2",4"-dichlorophenox~y)-pheno~y]-valeric acid (o. E~ample 1j were ~leated to 60 C together with 30 ml of toluer.e . and 12 g OL thionyl chloriAe until the developmen~ o~ gai was ter i~
., _ 1 ' ~, , , ~. . .

1108~68 nated. Toluene and thionyl chloride in excess were then distil-led o~f under reduc~d pressure. The remaining oil was take;l up in toluene and added dropwise to a solution of 6 y of n-pro-panol and 8.5 g o~ triethylamine in 50 ml of toluene. After the addition, stirring was continued ~or 1 hour at 50 C, the triethylamino-hydrochloride was filtered off and washed with water. After removal of the solvent, the reaction product w~.s distilled in a high vacuum. 27.5 g of ~-[~'-(2",4"-dichloro-phenoxy)-phenoxy]-valeric acid n-propyl ester boiling at 20C C/
0.01 bar were obtainedO

Cl ~ -0- ~ --0-~Ei-CH~CH2-C~
~ Cl \ C~2C~2'~

1~

1108iÇi8 _X A M P L E 6:
~-[~ trifluoromethy~er.o~:~)- heno~y]-?en,a ol-1 20.4 g of 4-[4'-(4'`-trifluorome~hylphenoxy)-pheno~]-va-leric acid isobutyl ester (0c Example 7) were added dro~wise t~
a suspension of 1.25 g of lithium-aluminum hvdride in 50 ml 0c ether. When the addition was terminat2d, the mixture was rerl-~
ed for 1 hour ~lhile stirring. 10 ml of ethyl acetate and then 40 ml of water were added slowly. Fina].ly, 2N a2so4 was adde~
while vi.gorously stirring until the aluminum hydroxide preci~i-tate had dissolved. The ether phase was washed neutral with sodium bicarbonate solution and ~he solvent distilled off unde-reduced pressure. After di.stillation in a high vacuum 15.4 g = 90.5 % of the theory of 4-[4'-(4"-trifluoromethylpnenoxy~-phenoxy~-pentanol 1 boiling at 174 C~0.07 i~ar were o~tain~d.

CF~- ~ -0~ ~ -0--CH-C~I~Cll2CI-T70-~

. :
E X A M P _ E 7:
1-chloroacetYloxy-4-[4~-(4~-trl.f]~ ~ x~)-phc_o~
pentane 6.45 g of chloroacetyl chloride. were added dropwise at ~ocm temperature to a solution of 17.0 g of 4-[4'-~4"--trifluoro~ethy~-phenoxy)-phenoxy]-~entanol-1 and 5.55 g of tri.ethylamine in ~O ~l of ab.solute toluene. After the addition, sti.rril1g of the mixtu~e was continued or 1 hour at 50 C, the precipitate was filtered off, the toluene solution washed with dilute hydrochloric aci.d and watex and dried. After remo-~al of the solve~t, 18.5 g =
83 % of the theory of 1-chloroac2tylo~y -[4'-(4"-triIluorome~hyl-~`` ~o~

phenoxv)-phenoxy]-pentc.ne were obtained.

C~ Cr'" ct.'2 -C~ 2 -C-C-CU~

The following compounds were prepared in analogous manner:
8) 1-benzoylo~ 4-[4'-(4"-trifluoromethylphenoxy)-phenoxy]~
pentane. :
9) 1 methylsulfonyloxy-4-[4'-(4"-trifluorometllylphenoY~y)-phenoxy]-pentane.
10) 1-N,N-dimethylcarbamoyloxy-4-~4~-(4"-trifluoromethylpheno~y)-phenoxy]-pentane.
For the prepa;-ation of the latter compound stirri.ng of the reaction mixture was continued for about 10 hours at 60 C.
: Further compounds of formula I obtainable accGrding to .h_ . . .
precodil1g ~xamples are listed in the followiny takl~..

, r .

, . "

. . . . .

-- .

A B L E: Cll~
O - Cll -C112 -C112- Z

Example I I
No (R)n Z physical prepared accord-data in~ to Example 11 2,4-Cl2 -COOCH3 4 12 4~Cl -COOCH3 4 13 2,4-C12 -COOC2H5 6 14 2,4-C12 -COOC3H7(i) 6 4-Cl -COOC3H7(n) 7 16 4-C~3 -COOC8Hl7(n) 7 17 4-CF3 -CcH2cH2cl 6 18 4-Cl -COOCH2CH20CH3 7 2,4-Cl2 -COOCH2CH20CH3 6 21 4-CF3 -COOCH~CH2Cl)2 6 22 4-CF3 -Coo-(cH2cH2o)2c2H5 7 23 4-CF3 -Coo(cH2)2ocH2(cH2)2 3 7 24 4-CF3 -COO-CH2 - ~) 6 4-CF3 -Cc~l2cH2~l 26 4-CF3 ¦ -CcH2cH2scll3 6 27 4-CF3 -COO ~ Cl 6 28 ~ 4-CF3 ~ -COO-CHz CH=CH2 ~ ~ 6 ~f~
~ .
.. . .

. ~:

.
-~i¢1`8~6~

T A B L E ~cont.) .

Example (R) _ physical prepared accord-No. n data ing to Example 29 4-CF3 -C-cH2-c - Cl-l 6 302,4-CI~ -C~ 1~ ~ Cl ~ 6 332,4-C12 -COOMg 1/2 344-Br-2-Cl -COOCH3 4 354-Br-2-Cl -COOCH2-CH(CH3)2 7 r-. -A

' ~

.
, , .
. .

J 11~81~ii8 HO~ 76/F 200 ~IOLOGICAL EXAMPLES
E X A ~1 P L E I:
Seeds Of grasses were sown in pots and the surface of the soil was sprayed with compoc;itions according to the invention in the form of wettable powders in different concentrations.
The pots were placed for 4 weeks in a greenhouse. The result of the treatment was evaluated according to the scheme of Bolle (Nachrichtenblatt des Deutschen Pflanzenschutzdienstes, 16, 1964, 92 - 94) /
Evaluation Damaging action in % on n~r ~eeds Crops 2 97.5 to ~100~ 0 to 2.5 3 95 to ~ 97.5 ~ 2.5 to 5 `. 4 90 to < 95 ~ 5 to 10 85 to ~ 90 ~ 10to 15 . 6 75 to < 85 ~15 to 25 7 65 to < 75 ~25 to 35 8 32.5 to < 65 ~ ~35 to 67.5 9 0 to <32.5 >67.5 to 100 :
The test resulLs in the following table show that the com--pounds of the invention exhibit an excellent herbicidal action even in a very low concentrat:ion in pre-emergel1ce as well as ~: irl pos~-emeIgellce pr~cesses.

- 16 ~

` 1~0~168 HGE_7j/F 2~0 T A B L E 1: ~
_ E~ ple dose - EC SA DI AL
(Xg ~S ~ ) 17 2.5 pre 0.6 1 1 1 2 2.5 post 3 2.5 pre 1 1 - 2 0~6 1 1 - 3 - 2.5 post 1 1 - 1 0.6 1 1 - 1 2.8 2l5 pre 0~6 2,5 post 1 1 _ 0-6 1 1 ~ 3 16 2.S pre 2?5 post 1 1 .
- 0~6 1 1 - 1 8 2-5 pre Ot6 1 1 - 2 2~5 p~st 1 - 1 - 1 0~6 1 1 - 1 13 2.5 p~e 1 1 - 1 0,6 2.5 post 0~6 ~ 2.6 ~5 pre 1 1 - 2 ;; 0.6 1 1 - 2 2~5 pc~st Oq6 1 1 - 1 legends: AS -- active substance .~ . pre = pre-emergence . post = post-emergence EC = Echinochloa (barnyard grass) S~ - Setaria (brlstl.e grass) DI = Digitaxia (crabgrass~ :

Al. -- Alopecurus (annual blackgrass~

.
.

Claims (11)

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

in which R1 is halogen, CF3 or C1-C4 alkyl, Z is -CN, -CS-NH2, CO-R2 or -CH2-O-R3, R2 is hydroxy, -0-cat; C1-C12-alkoxy (optionally substituted by OH, halogen, CF3, C1-C6 alkoxy, C1-C4alkylthio, phenyl, phenoxy or halophenoxy), a radical of one of the formulae , , in which stands for the pyrrolidinyl, piperidinyl, morpholinyl or N-methyl-piperazinyl radical; C5-C6 cycloalkoxy (optionally substituted by C1-C4 alkyl, and/or halogen), C3-C4 alkenyloxy; cyclohexenyloxy; C3-C4 alkinyloxy (optionally substituted in l-position by C1-C4 alkyl and/or phenyl), phenoxy (optionally substituted by halogen, NO2 and/or C1-C4 alkyl), C1-C6 alkylthio, allylthio, phenylthio, halophenylthio, amino, C1-C4 alkylamino, hydroxyethylamino, di-C1-C4 alkylamino, pyrrolidino, piperidino, morpholino; anilino (optionally substituted by halogen, CF3 and/or C1-C4 alkyl); or hydrazino, R3 is hydrogen, C1-C4 alkyl, C1-C4 alkylcarbonyl, halo-C1-C4 alkylcarbonyl, benzoyl (optionally substituted by halogen, NO2 and/or C1-C4 alkyl), C1-C4 alkylcarbamoyl, di-cl-c4alkylcarbamoyl, phenylcarbamoyl (optionally sub-stituted by halogen and/or C1-C3alkyl), C1-C4alkylsulfonyl, phenylsulfonyl, -SO3H or -SO3cat, cat is the cation equivalent of an inorganic or organic base, n is an integer of from 1 to 3 and m is an integer of from 1 to 6, on the proviso that when R1 is 4-CF3 n being 1, or R1 is 4-CF3 and 2-halogen, n being 2, then R2 is not hydroxy, an -0-cation group, lower alkoxy, C1-C4 alkylthio, amino, C1-C4 alkylamino or di-C1-C4 alkylamino.
2. A compound as claimed in claim 1, in which (R1)n represents 4-chloro, 4-trifluoromethyl or 2,4-dichloro and Z stands for a radical of the formula -CH2-0-R3 in which R3 has the indicated meaning.
3. A compound as claimed in claim 1, in which (R1)n represents 4-chloro or 2,4-dichloro and Z stands for a radical of the formula -CO-R2 in which R2 has the indicated meaning.
4. A compound as claimed in claim 3, in which (R1)n and Z have the indicated meaning and R2 represents hydroxy, -Ocat, C1-C12alkoxy optionally substituted by -OH, halogen, -CF3, C1-C6alkoxy, C1-C4alkylthio, phenyl, phenoxy, or halophenoxy; radicals of the formula or -(OC2H4)2-3 - OCmH2m-l ;
C5-C6cycloalkoxy optionally substituted by Cl-C4 alkyl and/or halogen;
C3-C4alkenyloxy, cyclohexenyloxy, C3-C4alkinyloxy optionally substituted in 1-position by C1-C4alkyl and/or phenyl; phenoxy optionally substituted by halogen, NO2 and/or C1-C4 alkyl; C1-C6alkylthio, allylthio, phenylthio halophenylthio and m stands for an integer from 1 to 6.
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 compound as claimed in claim 1, having the formula
9. A compound as claimed in claim 1, having the formula
10. A process for preparing a compound of formula I as claimed in claim 1, which comprises a) reacting a compound of formula II

with a compound of formula III
in which Z .is a halogen atom or the mesylate or tosylate radical, in the presence of a base, or b) reacting a compound of formula II with .gamma.-valerolaction of formula (IV) in the presence of a base, and optionally transforming the compound of formula I into another compound of formula I by saponification, esterification, salt formation, transesteri-fication, amidation, dehydration, hydration, reduction, or oxidation.
11. Method for controlling the growth of undesired weed grasses which comprises treating the infested area with an effective amount of a compound as claimed in claim 1.
CA285,393A 1976-08-25 1977-08-24 Herbicides Expired CA1108168A (en)

Applications Claiming Priority (2)

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CH1079576A CH624087A5 (en) 1976-08-25 1976-08-25 Process for the preparation of phenoxyphenoxypropionic acid derivatives
CH10795/76 1976-08-25

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DE2223894C3 (en) * 1972-05-17 1981-07-23 Hoechst Ag, 6000 Frankfurt Herbicidal agents based on phenoxycarboxylic acid derivatives
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
GB1519147A (en) * 1974-09-30 1978-07-26 Lafon Labor Sulphur and oxygen-containing diaryl compounds
GB1560416A (en) * 1975-09-03 1980-02-06 Rohm & Haas Trifluoromethylphenyl derivatives
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OA05754A (en) 1981-05-31
SU727106A3 (en) 1980-04-05
ATA609777A (en) 1979-08-15
GB1583509A (en) 1981-01-28
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FR2362816B1 (en) 1984-02-10
BE858104A (en) 1978-02-27
AT355863B (en) 1980-03-25
PL109937B1 (en) 1980-06-30
EG13015A (en) 1980-07-31
PT66952A (en) 1977-09-01
IL52810A (en) 1982-03-31
DE2733179C2 (en) 1986-11-13
DE2733179A1 (en) 1978-05-18
FR2362816A1 (en) 1978-03-24
IL52810A0 (en) 1977-10-31
AU509671B2 (en) 1980-05-22
PL200438A1 (en) 1978-04-24
HU179199B (en) 1982-09-28
IT1085267B (en) 1985-05-28
BR7705631A (en) 1978-05-30
CH624087A5 (en) 1981-07-15

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