GB2266305A - Herbicidal pyridine derivatives - Google Patents
Herbicidal pyridine derivatives Download PDFInfo
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- GB2266305A GB2266305A GB9208088A GB9208088A GB2266305A GB 2266305 A GB2266305 A GB 2266305A GB 9208088 A GB9208088 A GB 9208088A GB 9208088 A GB9208088 A GB 9208088A GB 2266305 A GB2266305 A GB 2266305A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon 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
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Novel herbicidal compounds have the general formula: <IMAGE> wherein R is a group of the formula: <IMAGE> and X is oxygen or sulphur; R<1>, R<2>, R<3>, R<5>, R<6>, R<7>, R<8>, and R<12> are each independently OMe, OAc, OCH2Ph or H, R<4> is H, CH2OMe, CH2OAc, or CH2OCH2Ph, and R<9> is H, or wherein R<9> and R<5> taken together or R<5> and R<6> taken together or R<6> and R<7> taken together are a group of the formula: <IMAGE> or R<6> and R<12> taken together are a group of the formula (F) or of the formula: <IMAGE> and the remaining substituents are as previously defined and wherein R<10> and R<11> are each independently H, C1-4 alkyl or aryl.
Description
HERBICIDALLY ACTIVE ESTERS OF TRICLOPYR
The present invention relates to carbohydrate derivative esters of 3,5,6-trichloro-2-pyridyloxyacetic acid (having the common name triclopyr) to processes for their preparation, herbicidal compositions containing them, and to methods for their use.
Triclopyr is a known broad-leaved herbicide having the formula
Although safe to whea.t, triclopyr is phytotoxic. tn various other commercially important crops (e.g., b2rley, cotton, rape, soya and sugar beet) at doses normally required to control broad-leaved weeds. The free form of triclopyr is therefore unsuited to use with these crops.
EP-A-0247721 (The Dow Chemical Compally) discloses various polyol esters of triclopyr which display reduced phytotoxicity to triclopyr-sensitive crops compared to triclopyr itself.
It has now surprisingly been found that esterification of triclopyr with alkyl, benzyl, acetyl and iso-alkylidene substituted pentoses or hexoses can also reduce phytotoxicity across a broad spectrum of triclopyrsensitive crops. Moreover, the activity of many of these esters against broad-leaved weeds is actually enhanced over the corresponding activity of free triclopyr.
Accordingly, the present invention provides a compound of the general formula:
wherein R is a group of the formula:
X is oxygen or sulphur;
R1, R2, R3, R5, R6, R7, R8, and R12 are each independently
OMe, OAc, OCH2Ph or H; R4is H, CH2OMe, CH2OAc, or CH2OCH2Ph, and R9 is H,
or wherein
R9 and R5 taken together or R5 and R6 taken together or R6 and R7 taken together are a group of the formula:
or R6 and R12 taken together are a group of the formula (F) or of the formula:
and the remaining substituents are as previously defined and wherein R10 and R11 are each independently H, C14 alkyl or aryl.
Preferably in the present invention, X is oxygen.
Suitably, R1, R2, R3,, 25, R6, R7, R8 and R12 are each either
OAc or OMe and R4 is suitably either CH2OAc or CH2OMe.
Preferred compounds cf the present invention are:
(3,5,6-trichloro-2-pyridyloxyacetyl) 2,3,4,6-tetra-O- methyl-D-glucopyranose;
(3,5,6-trichloro-2-pyridyloxyacetyl) 2,3,4, 6-tetra-O- acetyl-D-mannopyranose;
(3,5,6-trichloro-2-pyridyloxyacetyl) 2,3,4-tri-O-acetyl
D-ribose; (3,5, 6-trichloro-2-pyridyloxyacetyl) 1,2,3, 4-tetra-O- acetyl-D-glucopyranose;
(3,5,6-trichloro-2-pyridyloxyacetyl) 2,3:4, 5-di-O- (isopropylidene)-B-D-fructopyranose;
(3,5,6-trichloro-2-pyridyloxyacetyl) 2,3:4, 6-di-O- (isobutylidene)-a-L-sorbofuranose; or
(3,5,6-trichloro-2-pyridyloxyacetyl) methyl 2,3-0 (isopropylidene)-D-ribofuranoside.
The present invention also provides a process for the preparation of the foregoing compounds which process comprises reacting 3,5,6-trichloro-2-pyridyloxyacetic acid or a derivative thereof with an alcohol of the formula R-OH or a derivative thereof wherein R is a group of the formula
B, C, D or E as defined above.
Also provided is a herbicidal composition comprising a compound of the present invention with an agricultural adjuvant or carrier or an additional active ingredient.
Advantageously, the active substances according to the invention or mixtures thereof are used in the form of preparations, for example, powders, sprayable agents, granulates, solutions, emulsions or suspensions, with the addition of liquid and/or solid carriers or diluents and, if desired, wetting agents, adhesion-promoting agents, emulsifiers and/or dispersing agents, but preferably in the form of emulsions and emulsifiable concentrates.
Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarbons, such as, for example, benzene, toluene and xylene, cyclohexanone, isophorone, dimethyl sulphoxide, dimethylformamide, and also mineral oil fractions.
Suitable solid carriers are, for example, mineral earths, for example, tonsil, silica gel, talcum, kaolin, attaclay, limestone, silica acid and vegetable products, for example, meals.
The preparation advantageously includes a surface-active substance(s). Suitable surface-active substances are, for example, calcium ligninsulphonate, polyoxyethylene alkylphenol ethers, naphthalenesulphonic acids and salts thereof, phenolsulphonic acids and salts thereof, formaldehyde condensates, fatty alcohol sulphates and substituted benzenesulphonic acids and salts thereof.
The proportion of the active substance(s) in the various preparations may vary within wide limits. For example, the preparations may contain from 5 to 95 percent by weight of active substances, from 95 to 5 percent by weight of liquid or solid carriers and, if desired, up to 20 percent by weight of surface-active substances.
The present invention further provides a method for controlling or preventing growth of weeds, which method comprises applying to the weeds or to a locus in which it is desired to prevent weed growth a compound or compos tion of the present invention.
Preferably in the latter method the weeds are broadleaved weeds such as Coffee weed, Cocklebur, Jimson weed,
Lambsquarters, Morning Glory, Pigweed, Velvet-leaf or Wild
Buckwheat.
Suitably in said method the compound is applied in a total amount of from 0.2 to 2 kg/ha, preferably from 0.5 to 1.2 kg/ha.
In the method of the present invention the said compound may be applied to a crop area or an area adjacent to a crop area. The crop area may for example be a cotton, oilseed rape, sugar beet or soya bean area.
The compounds or preparations may be applied in customary manner, for example, using water as carrier in quantities of spraying liquor of from 100 to 1000 litres/ha. It is possible to use the agents in the socalled low volume and ultra low volume processes, and also to apply them in the form of so-called micro-granules.
The particular nature of the present invention will readily be understood from the following non-limiting
Examples, in which "m.p." denotes "melting point".
Example 1
A. 2,3,4,6-tetra-O-methyl-D-qlucopvranose (I)
D-glucose was exhaustively methylated and then
hydrolysed as described by West and Holden
(Organic Syntheses, Collective Volume III
(Horning E.C., Ed.). John Wiley and Sons Inc..
New York 1955, pp 800-802) to provide the title
compound (I; see below)
B. (3,5, 6-trichloro-2-vridv1oxvacetv1) 2,3,4, 6-tetra-O-methvl-D-alucovranose (II)
A 0.25M solution of 3,5,6-trichloro-2
pyridyloxyacetic acid in dry THF was stirred at
ambient temperature with an equivalent of 1,1
carbonyldiimidazole for 1 hour, after which time
all gaseous evolution had ceased and a clear
solution was obtained.
A 0.5M solution of derivatised carbohydrate
compound I in dry THF was added and the mixture
stirred for several hours and then allowed to
stand overnight. The solvent was removed under
reduced pressure and the residue partitioned
between equal amounts of methylene chloride and
water. The organic phase was washed with two
further quantities of water and then dried over
anhydrous magnesium sulphate. Removal of the
solvent gave the title ester (compound IIj in
good yield.
Compound II was purified by distillation to
provide a pale yellow syrup (boiling point 2350C at 0.05mm Hg).
The proton NMR spectrum for compound II was recorded in CDC13 on a Varian (Trade Mark) EM390 spectrometer and confirmed the structure proposed above.
Elemental Analysis
C H N
Calculated 43.01 4.67 2.95
Observed 42.98 4.57 2.85
Example 2
A. 1,2,3. 4-tetra-O-acetvl-D-glucovranose (III)
D-glucose was tritylated, exhaustively acetylated
and then de-tritylated as described by Reynolds
and Evans (Organic Svntheses, Collective Volume
III (Horning E.C., Ed.) John Wiley and Sons
Inc., New York 1955, pp 432-434) to provide 1,2,3,4-tetra-O-acetyl-D-glucopyranose (Compound
III; see below) m.p. 1270C (cf literature value
m.p. 1290C; Reynolds and Evans suPra).
B. (3,5.6-trichloro-2-pvridvloxvacetvl) 1,2,3 4-tetra-O-acetvl-D-glucoovranose (IV)
The procedure of Example 1-B was repeated except
that Compound III from step A above was used in
place of Compound I to provide the title ester
(Compound IV) in good yield.
The Compound IV preparation was purified by flash
chromatography to provide a colourless solid with
a melting point of 62-640C.
The proton NMR spectrum for purified compound IV was recorded as described in Example 1 and confirmed the structure proposed above.
Elemental Analvsis C H N
Calculated 42.99 3.78 2.39
Observed 42.07 3.63 2.33
Example 3
A. 2.3,4. 6-tetra-O-acetYl-D-mannoDoranose (V)
D-mannose was condensed with 4-nitroaniline as
described by Weygand et al (Chem. Ber. 1951, 84
pp 594-602) to give a mannosylamine. Acetylation
of the mannosylamine followed by hydrolysis as
described by Douglas and Honeyrnan (J. Chem. Soc.
1955, pp 3674-3681) gave the title compound (V;
see below) m.p. 920C (cf literature value m.p.
1270C; Weygand et al suPra)
B. (3,5,6-trichloro-2pvridyloxvacetyl) 2,3,4, 6-tetra-O-acetvl-D-mannovranose (VI)
The procedure of Example 1-B was repeated except
that Compound V from Step A above was used in
place of Compound I to provide the title ester
(Compound VI) in good yield.
The Compound VI preparation was purified by flash
chromatography. Melting point was 52-55 C.
The proton NMR spectrum for purified Compound VI was recorded as described in Example 1 and confirmed the structure proposed above.
Elemental Analysis
C H N
Calculated 42.99 3.78 2.39
Observed 42.17 3.66 2.18
Example 4
A. 2,3:4, 5-di-O-(isoropryliene)-ss-D-fructopyranose
(VII)
D-fructose was condensed with acetone as
described by Brady (Carbohydrate Res. 1970, 15, pp 35-40) in the presence of sulphuric acid to
provide the title compound (VII; see below) in
good yield (m.p. 960C; (cf literature value L 970C (Brady supra))
B. (3.5,6-trichloro-2-pvridyloxyacetvl) 2,3:4,5-di- O-(isopropvlidene)-B-D-fructopyranose (VIII)
The procedure of Example 1-B was repeated except
that Compund VII from step A above was used in
place of Compound I to provide the title ester
(Compound VIII) in good yield.
Compound VIII was purified by distillation to
provide a colourless solid with a melting point
of 52-550C at 0.25 mmHg.
The proton NMR spectrum for purified Compound VIII was recorded as described in Example 1 and confirmed the structure proposed above.
Elemental Analysis
C H N
Calculated 45.76 4.45 2.81
Observed 45.95 4.45 2 73
ExamPle 5
A. 2,3:4, 6-di-O-( isobutylidene)-a-L-sorbofuranose (IX)
Ethylmethyl ketone was condensed with l-sorbose
in the presence of concentrated sulphuric acid as
described by Glass et al (Carbohydrate Res., 1973 26 181-189) to provide the title compound
(IX; see below) m.p. 93-990C (cf literature value
m.p. 96-990C; Glass et al suPra).
B. (3,5, 6-trichloro-2-oyridyloxyacetyl) 2,3:4, 6-di O-(isobutolidene)-a-L-sorbofuranose (X)
The procedure of Example 1-B was repeated except
that Compound IX from Step A above was used in
place of Compound I to provide the title ester
(Compound X) in good yield.
Compound X was purified by distillation to
provide a colourless solid with a melting point 40-42 C. Boiling point was 1500C at 0.2mm Hg.
The proton NMR spectrum for purified Compound X was recorded as described in Example 1 and confirmed the structure proposed above.
Elemental Analysis
C H N
Calculated 47.88 4.97 2.66
Observed 48.39 5.00 2.52
Example 6
A. (3,5, 6-trichloro-2-ovridvloxyacetyl) methyl 2,3-O-isopropvlidene-D-ribofuranoside (XII)
The procedure of Example 1-B was repeated except
that methyl 2, 3-O-isopropylidene-D
ribofuranoside (XI) purchased from Pfanstiehl
Laboratories Inc. was used in place of Compound I
to provide the title ester (XII) in good yield.
Compound XII was purified by recrystallisation
from benzene/hexane 1:1 to provide colourless
needless with a melting point of 71 - 72.50C.
The proton NMR spectrum for the purified Compound XII was recorded as described in Example 1 and confirmed the structure proposed above.
Elemental Analysis
C H N
Calculated 43.41 4.10 3.16
Observed 43.48 4.13 3.09
Example 7
A. 2,3, 4-tri-O-acetyl-D-ribose (XIII)
D-ribose was condensed with 4-nitroaniline as
described by Douglas and Honeyman (J. Chem. Soc.
1955, pp 3674-3681) and Honeyman (Methods in
Carbohydrate Chemistry Volume II (Whistler, R.L;,
Wolfrom, M.L., Eds.) Academic Press, New York, 1963, pp 95-99) to provide intermediate "i" (m.p 169-1750C; cf literature value m.p 1780C).
Intermediate "i" was acetylated as described by
Douglas and Honeyman suPra and by Honeyman suPra to provide intermediate "ii" (m.p. 45-9O0C).
Intermediate "ii" was then hydrolysed with dilute formic acid as described by Douglas and Honeyman suPra and by Honeyman suPra to provide the title compound (XIII; see below) in the form of a colourless syrup.
B. (3,5, 6-trichloro-2-ovridvloxyacetvl) 2,3, 4-tri-O-acetyl-D-ribose (XIV) The procedure of Example 1-B was repeated except
that ccmpound XIII from step A above was used in
place of Compound I to provide the title ester
(XIV) in good yield.
Compound XIV was purified by flash chromatography to provide a colourless solid with a melting
point of 580C.
The proton NMR spectrum for purified Compound XIV was recorded as described in Example 1 and confirmed the structure proposed above.
Elemental Analysis
C H N
Calculated 42.0 3.5 2.7
Observed 41 3.1 1.9
Example 8
Tests were carried out to compare the herbicidal efficiency of the esters of triclopyr prepared in Examples 1 to 7 against the herbicidal efficiency of triclopyr itself.
Method
Seeds were sown in rows in trays and allowed to germinate and grow untreated to a height of about 10 cm.
Plants were then sprayed with an aqueous solution or suspension of the respective esters or triclopyr at an initial concentration of 4000 mg litre'l followed by a sequence of 2-fold serial dilutions as necessary.
Phytotoxicity was evaluated at 14 days after treatment by visual assessment of treated plants compared to untreated plants grown under identical conditions. A scale of 0-100 was used with 0 representing no visible difference from the untreated plants and 100 indicating death of all plants.
By using a series of concentrations a growth reduction factor GR50 was calculated for each weed and crop type, indicative of the concentration of chemical achieving 50% of growth regulator.
Application was made to the following plants postemergently:
WEEDS:
Coffee weed Daubentonia texana
Cocklebur Xanthium sPinosum Jimson weed Datura stramonium
Lambs quarters Chenopodium album
Morning Glory Inomea sp.
Pigweed Amaranthus sp.
Velvet-leaf Abutilon theophrasti Wild Buckwheat Polyqonum convolvulus
CROPS:
Cotton GosoPium hirsutum
Oil seed rape Brassica naous Sugar beet Beta vulparis Soya bean Glycine max
In Table 1 the index BWT/BWE denotes the GR=o ratio for triclopyr to triclopyr ester with Broad-leaved weeds.
The index BCE/BCT denotes the GRjo ratio for triclopyr ester to triclopyr with Broad-leaved crops.
The indices SBE/SBT, ORE/ORT and SE/cT denote the GR50 ratios for triclopyr ester to triclopyr with Sugar Beet,
Oilseed Rape and Soya respectively.
The high values of each of these indices shows that the present compounds have enhanced activity against broadleaved weeds and enhanced crop safety to broad-leaved crops compared to free triclopyr itself.
Formulation Examples
The following Examples A to C are illustrations of typical formulations in which the compounds of the invention may be utilised.
A. Wettable Powder
a) 40 percent by weight of active substance
25 percent by weight of clay minerals
20 percent by weight of colloidal silica
10 percent by weight of cellulose pitch
5 percent by weight of surfactant based on a mixture of the calcium salt of lignin-sulphonic acid and alkylphenol polyglycol ethers.
b) 25 percent by weight of active substance
60 percent by weight of kaolin
10 percent by weight of colloidal silica
5 percent by weight of surfactant based on the sodium salt of N-methyl-N-oleyltaurine and the calcium salt of lignin-sulphonic acid.
c) 10 percent by weight of active substance
60 percent by weight of clay minerals
15 percent by weight of cellulose pitch
10 percent by weight of surfactants based on the sodium salt of N-methyl-N-oleyltaurine and the calcium salt of lignin-sulphonic acid.
B. Paste
45 percent by weight of active substance
5 percent by weight of sodium aluminium silicate
15 percent by weight of cetyl polyglycol ether with 8 moles of ethylene oxide
2 percent by weight of spindle oil
10 percent by weight of polyethylene glycol
23 percent by weight of water.
C. Emulsion Concentrate
a) 20 percent by weight of active substance
15 percent by weight of cyclohexanone
55 percent by weight of xylene
5 percent by weight of a mixture of nonylphenyl polyoxyethylenes and calcium dodecylbenzenesulphonate.
b) 10 percent by weight of active substance
6 percent by weight of cyclohexanone
36 percent by weight of xylene
12 percent by weight of a mixture of nonylphenyl polyoxyethylenes and calcium dodecylbenzenesulphonate
36 percent by weight of mineral oil having a high paraffin content.
Table 1
Postemergent herbicidal activities of esters of 3,5,6trichloro-2-pyridyloxyacetic acid
GR50 (pgml 1) Compound No. BWT/BWE BCE/BCT ssE/sBT ORE/ORT SE/ST II 1.06 1.66 2 > 1 2
IV 0.57 1.7 4 2 > 2
VI 0.45 3.29 4 > 2 > 2
VIII 0.74 1.88 1 1 8
X 1.25 1.08 1 0.25 4
XII 1.08 1.48 1 2 2
XIV 0.56 1.66 4 1 1
T = triclopyr E = triclopyr ester.
BW = Broad-leaved weeds: coffeeweed, cocklebur,
jimson weed, lambsquarters,
morning glory, pigweed,
velvet leaf, wild buckwheat.
BC = Broad-leaved crops: cotton, rape, soya, sugar
beet
SB = Sugar beet OR = Oilseed rape
S = Soya.
Claims (20)
1. A compound of the general formula:
wherein R is a group of the formula:
and X is oxygen or sulphur; R1, RZ, R3, R5, R6, R7, R8, and
R12 are each independently OMe, OAc, OCH2Pn or H, R4is H, CH2OMe, CH2OAc, or CH2OCH2Ph, and R9 i5 H, or wherein
R9 and R5 taken together or R5 and R6 taken together or R6 and R7 taken together are a group of the formula:
or R6 and R12 taken together are a group of the formula (F) or of the formula:
and the remaining substituents are as previously defied and wherein R10 and R11 are each independently H, C14 alkyl or aryl.
2. A compound as claimed in Claim 1 wherein X is oxygen.
3. A compound as claimed in Claim 1 or Claim 2 wherein R1 R2, R3,, R5, R6 R7, R8 and R12 are each OAc.
4. A compound as claimed in Claim 1 or Claim 2 wherein
R1, R2 R3 R5 R6 R7, R8 and R12 are each OMe.
5. A compound as claimed in any one of the preceding
Claims wherein R4 is CH2OAc.
6. A compound as claimed in any one of Claims 1 to 4 wherein R4 is CH2OMe.
7. A compound as claimed in any one of the preceding
Claims wherein R is a group of the general formula B as defined in Claim 1.
8. A compound as claimed in any one of Claims 1 to 6 wherein R is a group of the general formula C as defined in
Claim 1.
9. A compound as claimed in any one of Claims 1 to 6 wherein R is a group of the general formula D as defined in
Claim 1.
10. A compound as claimed in any one of Claims 1 to 6 wherein R is a group of the general formula E as defined in
Claim 1.
11. (3,5,6-trichloro-2-pyridyloxyacetyl) 2,3,4,6-tetra
O-methyl-D-glucopyranose; (3,5,6-trichloro-2-pyridyloxyacetyl) 2,3,4, 6-tetra-O- acetyl-D-mannopyranose;
(3,5,6-trichloro-2-pyridyloxyacetyl) 2,3 ,4-tri-O- acetyl
D-ribose; (3,5, 6-trichloro-2-pyridyloxyacetyl) 1,2,3, 4-tetra-0- acetyl-D-glucopyranose;
(3,5,6-trichloro-2-pyridyloxyacetyl) 2,3 :4,3-di-O- (isopropylidene)-D-D-fructopyranose; (3,5,6-trichloro-2-pyridyloxyacetyl) 2,3:4, 6-di-O- (isobutylidene)-a-L-sorbofuraose; or (3,5,6-trichloro-2-pyridyloxyacetyl) methyl 2,3-0 (isopropylidenej -D-ribofuranoside.
12. An ester substantially as hereinbefore described with reference to any one of Examples 1 to 7.
13. A process for the preparation of a compound as claimed in any one of the preceding Claims which process comprises reacting 3,5,6-trichloro-2-pyridyloxyacetic acid or a derivative thereof with an alcohol of the formula R-OH or a derivative thereof wherein R is a group of the formula
B, C, D or E as defined in Claim 1.
14. A process for preparing an ester of triclopyr as claimed in any one of Claims 1 to 12, said process being substantially as hereinbefore described with reference to any one of Examples 1 to 7.
15. A herbicidal composition which comprises a compound as claimed in any one of Claims 1 to 12 or a compound prepared by a process as claimed in Claim 13 or Claim 14 with an agricultural adjuvant or carrier or an additional active ingredient.
16. A method for controlling or preventing growth of weeds which method comprises applying to the weeds or to a locus in which it is desired to prevent weed growth a compound as claimed in any one of Claims 1 to 12 or a compound prepared by a process as claimed in Claim 13 or
Claim 14 or a composition as claimed in Claim 15.
17. A method as claimed in Claim 16 wherein the weeds are Coffee weed, Cocklebur, Jimson weed, Lambsquarters,
Morning Glory, Pigweed, Velvet-leaf or Wild Buckwheat.
18. A method as claimed in Claim 16 or Claim 17 wherein the said compound is applied in a total amount of from 0.2 to 2 kg/ha.
19. A method as claimed in any one of Claims 16 to 18 wherein the said compound is applied to a crop area or an area adjacent to a crop area.
20. A method as claimed in Claim 19 wherein the crop area treated is a cotton, oilseed rape, sugar beet or soya bean area.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9208088A GB2266305A (en) | 1992-04-13 | 1992-04-13 | Herbicidal pyridine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9208088A GB2266305A (en) | 1992-04-13 | 1992-04-13 | Herbicidal pyridine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB9208088D0 GB9208088D0 (en) | 1992-05-27 |
| GB2266305A true GB2266305A (en) | 1993-10-27 |
Family
ID=10713940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9208088A Withdrawn GB2266305A (en) | 1992-04-13 | 1992-04-13 | Herbicidal pyridine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2266305A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0247721A1 (en) * | 1986-05-28 | 1987-12-02 | The Dow Chemical Company | Alditol derivative esters of triclopyr , processes for their preparation and herbicidal compositions containing them |
-
1992
- 1992-04-13 GB GB9208088A patent/GB2266305A/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0247721A1 (en) * | 1986-05-28 | 1987-12-02 | The Dow Chemical Company | Alditol derivative esters of triclopyr , processes for their preparation and herbicidal compositions containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9208088D0 (en) | 1992-05-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |