GB2482299A - Use of a dialkylamide to reduce the phytotoxicity of an agrochemical - Google Patents

Use of a dialkylamide to reduce the phytotoxicity of an agrochemical Download PDF

Info

Publication number
GB2482299A
GB2482299A GB1012584.7A GB201012584A GB2482299A GB 2482299 A GB2482299 A GB 2482299A GB 201012584 A GB201012584 A GB 201012584A GB 2482299 A GB2482299 A GB 2482299A
Authority
GB
United Kingdom
Prior art keywords
butyl
iso
phenyl
dialkylamide
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
GB1012584.7A
Other versions
GB201012584D0 (en
Inventor
Gordon Alastair Bell
Anne Waller
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Syngenta Ltd
Original Assignee
Syngenta Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Syngenta Ltd filed Critical Syngenta Ltd
Priority to GB1012584.7A priority Critical patent/GB2482299A/en
Publication of GB201012584D0 publication Critical patent/GB201012584D0/en
Publication of GB2482299A publication Critical patent/GB2482299A/en
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Abstract

This invention relates to a method of reducing phytotoxicity of an agrochemical comprising mixing the agrochemical with a dialkylamide. Further embodiments of the present invention also include uses of a dialkylamide to reduce the phytotoxicity of an agrochemical. The specified agrochemicals are azoxystrobin, difenoconazole and isopyrazam. Preferably, the dialylamide is dimethyl lactamide, diethyl lactamide, dipropyl lactamide, dibutyl lactamide, dipentyl lactamide or dihexyl lactamide. Further actives may be included in the compositions.

Description

PHYTOTOXICITY REDUCTION METHODS
This invention relates to a method of reducing phytotoxicity of an agrochemical comprising mixing the agrochemical with a dialkylamide. Further embodiments of the present invention also include uses of a dialkylamide to reduce the phytotoxicity of an agrochemical.
Fledgling agrochemicals at various stages of development, which would otherwise hold out such promise in helping to feed the burgeoning global population, have their development dropped during research stages due to problems with phytotoxicity. In the process, millions of dollars of research is wasted and precious crop yield is lost.
Herbicide safeners are agents applied alongside herbicides to make them "safer" -i.e. to reduce the phytotoxic effect of the herbicide on crop plants, and to improve selectivity between crop plants and weed species which are ideally targeted by the herbicide. Herbicide safeners can be used to pretreat crop seeds before they are planted, or they can be sprayed on plants as a mixture with the herbicide.
However, safeners presently available are expensive to produce, and require sophisticated selection based upon the agrochemical they are to be combined with, and potentially may contribute to cases of crop tolerance.
Surprisingly, it has been found that by mixing the agrochemical with a dialkylamide, the phytotoxic effects of the agrochemical can be reduced.
Preferably, the dialkylamide is of formula (I) CH3CH(OH)C(=O)NR1R2 (I) where R' and R2 are each independently hydrogen; or C1-C6 alkyl, C2-C6 alkenyl or C3-C6 cycloalkyl, each of which is optionally substituted by up to three substituents independently selected from phenyl, hyciroxy, C-C5 alkoxy, morpholinyl and NR3R4 where R3 and R4 are each independently C1-C3 alkyl; or phenyl optionally substituted by up to three substituents independently selected from C 1-C3 alkyl; or R' and R2 together with the nitrogen atom to which they are attached form a morpholinyl, pyrrolidinyl, piperidinyl or azepanyl ring, each of which is optionally substituted by up to three substituents independently selected from C1-C3 alky!.
Even more preferably, the compound of formula (I) R' is not hydrogen, methyl, ethyl, propyl, n-butyl, sec-butyl, iso-butyl, n amyl, iso amyl, iso-butylenyl, n-hexyl, 1 -3-dimethylbutyl, allyl, CH2CH2OH, 2 hydroxypropyl, 2-hydroxy-isobutyl, 1,3-dihydroxy-2-rnethyl-2-propyl, tris-hydroxy-methyl-methyl, CH2CH2OCH3, cyclohexyl, phenyl, benzyl, ct-methylbenzyl, 3-phenylethyl, 3-hydroxypropyl or 1-hydroxy-2-butyl when R2 is hydrogen; R1 is not methyl, ally! or phenyl when R2 is methyl; R1 is not ethyl when R2 is ethyl; R1 is not n-butyl when R2 is n-butyl; R' is not iso-butyl when R2 is iso-butyl; R' is not n-amy! when R2 is n-amyl; R1 is not iso-amy! when R2 is iso-amy!; R1 is not n-hexy! when R2 is n-hexy!; R1 is not ally! when R2 is al!yl; R1 is not butyl or pheny! when R2 is phenyl; R1 is not benzy! when R2 is benzyl; R1 is not CH2CH2OH or ethyl when R2 is CH2CH2OH; R' is not 2-hydroxypropyl when R2 is 2-hydroxypropyl; and R' and R2 together with the nitrogen atom to which they are attached do not form a morpholinyl, pyrrolidiny! or piperidiny! unsubstituted ring.
More preferably the dialkylamide is dimethy! !actamide, diethy! !actamide, dipropyl lactamide, dibutyl lactamide, dipentyl lactamide or dihexy! lactamide.
Most preferably the dia!kylamide is dimethyl lactamide.
In one embodiment of the invention, the method includes the mixing of a dialkylamide and an agrochemical in the form of an emulsion concentrate (EC) or dispersion concentrate (DC).
EC formulations conventionally contain an active ingredient, one or more surfactants which act as emulsifiers upon dilution of the EC with water and a water immiscible solvent. Typical solvents for conventional EC formulations are aromatic hydrocarbons. These solvents have very low solubilities in water and a high capability of dissolving a wide range of active ingredients.
In a further embodiment, the method of the present invention may further comprise the addition of one or more active ingredients (AIs) to the dialkylarnide. Suitable AIs include, but are not limited to, herbicides, insecticides, growth regulators, fungicides, miticides and acaricides. The dialkylamide may also be combined with fertilizers, plant nutritionals, micronutrients, agrochemicals, paraffinic mineral oil, methylated seed oils (i.e. methylsoyate or methylcanolate), vegetable oils (such as soybean oil and canola oil), water conditioning agents such as Choice® (Loveland Industries, Greeley, CO) and Quest (Helena Chemical, Collierville, TN), modified clays such as Surround® (Englehard Corp.,), foam control agents, adjuvants, surfactants, wetting agents, dispersants, emulsifiers, deposition aids, antidrift components, and water.

Claims (13)

  1. Claims 1. A method of reducing phytotoxicity of an agrochemical comprising mixing the agrochemical with a dialkylamide.
  2. 2. A method according to claim 1, wherein the dialkylamide is of formula (I) CH3CH(OR)C(=O)NR1R2 (I) where R1 and R2 are each independently hydrogen; or C1-C6 aikyl, C2-C6 alkenyl or C3-C6 cycloalkyl, each of which is optionally substituted by up to three substituents independently selected from phenyl, hydroxy, C 1-C5 alkoxy, morpholinyl and NR3R4 where R3 and R4 are each independently C1-C3 alkyl; or phenyl optionally substituted by up to three substituents independently selected from C1-C3 alkyl; or R' and R2 together with the nitrogen atom to which they are attached form a morpholinyl, pyrrolidinyl, piperidinyl or azepanyl ring, each of which is optionally substituted by up to three substituents independently selected from C1-C3 alkyl.
  3. 3. A method according to claim 2, wherein in the compound of formula (I) R' is not hydrogen, methyl, ethyl, propyl, n-butyl, sec-buty!, iso-butyl, n amyl, iso amy!, iso- butylenyl, n-hexyl, 1 -3-dimethylbutyl, ally!, CH2CH2OH, 2 hydroxypropyl, 2-hydroxy-isobutyl, 1,3-dihydroxy-2-methyl-2-propyl, tris-hydroxy-methy!-methy!, CH2CH2OCH3, cyclohexyl, phenyl, benzyl, a-methylbenzyl, 3-pheny1ethyl, 3-hydroxypropyl or 1 -hydroxy-2-butyl when R2 is hydrogen; R1 is not methyl, ally! or phenyl when R2 is methyl; R' is not ethyl when R2 is ethyl; R' is not n-butyl when R2 is n-butyl; R' is not iso-butyl when R2 is iso-butyl; R1 is not n-amyl when R2 is n-amyl; R' is not iso-amyl when R2 is iso-amyl; R' is not n-hexyl when R2 is n-hexyl; R1 is not ally! when R2 is ally!; R' is not butyl or phenyl when R2 is phenyl; R' is not benzyl when R2 is benzyl; R' is not CH2CH2OH or ethyl when R2 is CH2CH2OH; R' is not 2-hydroxypropyl when R2 is 2-hydroxypropyl; and R' and R2 together with the nitrogen atom to which they are attached do not form a morpholinyl, pyrrolidinyl or piperidinyl unsubstituted ring.
  4. 4. A method according to any preceding claim, in which the dialkylamide is selected from the group consisting of dimethyl lactamide, diethyl lactamide, dipropyl lactamide, dibutyl lactamide, dipentyl lactamide or dihexyl lactamide.
  5. 5. A method according to any preceding claim, wherein the agrochemical is selected from the group consisting of strobilurins, succinate dehydrogenase inhibitors, and triazoles.
  6. 6. A method according to any preceding claim, wherein the agrochemical is azoxystrobin.
  7. 7. A method according to any preceding claim, wherein the dialkylamide and agrochemical are formulated as a dispersion concentrate (DC) or emulsion concentrate (EC).
  8. 8. Use of a dialkylamide to reduce the phytotoxicity of an agrochemical.
  9. 9. Use of a dialkylamide according to claim 8, wherein the dialkylamide is of formula (I) CH3CH(OH)C(=O)NR'R2 (I) where R' and R2 are each independently hydrogen; or C 1-C6 alkyl, C2-C6 alkenyl or C3-C6 cycloalkyl, each of which is optionally substituted by up to three substituents independently selected from phenyl, hydroxy, C1-C5 alkoxy, morpholinyl and NR3R4 where R3 and R4 are each independently C 1-C3 alkyl; or phenyl optionally substituted by up to three substituents independently selected from C1-C3 alkyl; or R1 and R2 together with the nitrogen atom to which they are attached form a morpholinyl, pyrrolidinyl, pipendinyl or azepanyl ring, each of which is optionally substituted by up to three substituents independently selected from C1-C3 alkyl.
  10. 10. Use of a dialkylamide according to claim 9, wherein in the compound of formula (I) R1 is not hydrogen, methyl, ethyl, propyl, n-butyl, sec-butyl, iso-butyl, n amy!, iso amyl, iso-butylenyl, n-hexyl, 1 -3-dimethylbutyl, allyl, CH2CH2OH, 2 hydroxypropyl, 2-hydroxy-isobutyl, 1,3-dihydroxy-2-methyl-2-propyl, tris-hydroxy-methyl-methyl, CH2CH2OCH3, cyclohexyl, phenyl, benzyl, a-methylbenzyl, 3-phenylethy1, 3-hydroxypropyl or 1-bydroxy-2-butyl when R2 is hydrogen; R' is not methyl, ally! or phenyl when R2 is methyl; R1 is not ethyl when R2 is ethyl; R1 is not n-butyl when R2 is n-butyl; R1 is not iso-butyl when R2 is iso-butyl; R1 is not n-amy! when R2 is n-amyl; R1 is not iso-amy! when R2 is iso-amy!; R' is not n-hexyl when R2 is n-hexyl; R1 is not ally! when R2 is ally!; R1 is not butyl or phenyl when R2 is phenyl; R' is not benzyl when R2 is benzyl; R1 is not CH2CH2OH or ethyl when R2 is CH2CH2OH; R' is not 2-hydroxypropyl when R2 is 2-hydroxypropyl; and R' and R2 together with the nitrogen atom to which they are attached do not form a morpholinyl, pyrrolidinyl or piperidinyl unsubstituted ring.
  11. I!. A method of controlling an agricultural pest comprising application to the pest, to a locus comprising it or to a surface on which it is capable of being present, of a pesticidally effective amount of a composition according to any one of claims 1 to 10.
  12. 12. A method of controlling an agricultural pest according to claim 11, wherein the pest is a fungus, the locus is vine or pomaceous fruit, and the composition comprises an agrochernical selected from the group consisting of azoxystrobin, difenoconazole or isopyrazam.
  13. 13. A dialkylamide or agrochemical, as defined in any preceding claim, when present in a method according to claim 1.
GB1012584.7A 2010-07-27 2010-07-27 Use of a dialkylamide to reduce the phytotoxicity of an agrochemical Withdrawn GB2482299A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1012584.7A GB2482299A (en) 2010-07-27 2010-07-27 Use of a dialkylamide to reduce the phytotoxicity of an agrochemical

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1012584.7A GB2482299A (en) 2010-07-27 2010-07-27 Use of a dialkylamide to reduce the phytotoxicity of an agrochemical

Publications (2)

Publication Number Publication Date
GB201012584D0 GB201012584D0 (en) 2010-09-08
GB2482299A true GB2482299A (en) 2012-02-01

Family

ID=42752853

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1012584.7A Withdrawn GB2482299A (en) 2010-07-27 2010-07-27 Use of a dialkylamide to reduce the phytotoxicity of an agrochemical

Country Status (1)

Country Link
GB (1) GB2482299A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013149993A1 (en) * 2012-04-04 2013-10-10 Syngenta Participations Ag Pesticidal composition
CN106795097A (en) * 2014-10-03 2017-05-31 普拉克生化公司 The production method of N, N dialkyl group lactamide
US20220369631A1 (en) * 2021-05-06 2022-11-24 Stoller Enterprises, Inc. Stable S-(+)-Abscisic Acid Nonaqueous Liquid Solutions

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007107745A2 (en) * 2006-03-22 2007-09-27 Syngenta Limited Process for producing lactamide compounds, new lactamide compounds and formulations containing lactamide compounds
EP1961302A1 (en) * 2007-02-23 2008-08-27 Cognis IP Management GmbH Biocide compositions comprising at least one dialkylamide based on oleic or linoleic acid
EP1961301A1 (en) * 2007-02-22 2008-08-27 Cognis IP Management GmbH Biocide compositions comprising a dialkylamide of a hydroxycarboxylic acid
WO2008145063A1 (en) * 2007-05-28 2008-12-04 Jiangsu Rotam Chemistry Co., Ltd. Agrochemical composition and method for preparing and using the same
WO2009027626A2 (en) * 2007-08-24 2009-03-05 Syngenta Limited Improvements in or relating to organic compounds

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007107745A2 (en) * 2006-03-22 2007-09-27 Syngenta Limited Process for producing lactamide compounds, new lactamide compounds and formulations containing lactamide compounds
EP1961301A1 (en) * 2007-02-22 2008-08-27 Cognis IP Management GmbH Biocide compositions comprising a dialkylamide of a hydroxycarboxylic acid
EP1961302A1 (en) * 2007-02-23 2008-08-27 Cognis IP Management GmbH Biocide compositions comprising at least one dialkylamide based on oleic or linoleic acid
WO2008145063A1 (en) * 2007-05-28 2008-12-04 Jiangsu Rotam Chemistry Co., Ltd. Agrochemical composition and method for preparing and using the same
WO2009027626A2 (en) * 2007-08-24 2009-03-05 Syngenta Limited Improvements in or relating to organic compounds

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013149993A1 (en) * 2012-04-04 2013-10-10 Syngenta Participations Ag Pesticidal composition
US11871748B2 (en) 2012-04-04 2024-01-16 Syngenta Participations Ag Pesticidal composition
CN106795097A (en) * 2014-10-03 2017-05-31 普拉克生化公司 The production method of N, N dialkyl group lactamide
US10144702B2 (en) * 2014-10-03 2018-12-04 Purac Biochem B.V. Method for the manufacture of N,N-dialkyllactamide
US20220369631A1 (en) * 2021-05-06 2022-11-24 Stoller Enterprises, Inc. Stable S-(+)-Abscisic Acid Nonaqueous Liquid Solutions
US11589582B2 (en) * 2021-05-06 2023-02-28 Stoller Enterprises, Inc Stable S-(+)-abscisic acid nonaqueous liquid solutions
US11606954B2 (en) 2021-05-06 2023-03-21 Stoller Enterprises, Inc. Stable S-(+)-abscisic acid nonaqueous liquid solutions
US11617368B2 (en) 2021-05-06 2023-04-04 Stoller Enterprises, Inc. Stable S-(+)-abscisic acid nonaqueous liquid solutions

Also Published As

Publication number Publication date
GB201012584D0 (en) 2010-09-08

Similar Documents

Publication Publication Date Title
WO2004080180A1 (en) Acaricide
AU2014310573A1 (en) Growth regulator concentrate and use thereof
JP6856662B2 (en) Dendrimer and its preparations
CA2449834C (en) Herbicidal compositions comprising benzoylpyrazoles and safener
GB2482299A (en) Use of a dialkylamide to reduce the phytotoxicity of an agrochemical
US6852674B2 (en) Herbicidal mixture comprising a benzoyl derivative, a fertilizer containing nitrogen and an adjuvant
KR101819051B1 (en) Formulations
WO2012057610A2 (en) A potentiator for soluble liquid herbicide
JP2016502548A (en) How to control resistant harmful plants
EP3593637B1 (en) Plant growth regulator concentrate and use thereof
US20060058191A1 (en) Pesticide solvent system for reducing phytotoxicity
WO2019034934A1 (en) Oil dispersable formulation
JP3590148B2 (en) Paddy field herbicide composition
AU2018283436B2 (en) Plant growth regulator and fungicide
JP3347778B2 (en) Herbicide composition
US20230109247A1 (en) Plant growth regulator and fungicide
JP3687928B2 (en) Herbicide composition for paddy field
EP3723486A1 (en) Compositions for the protection of agrarian crops and use thereof
NO861338L (en) SYNERGISTIC HERBICIDE MIXTURES.
JPH06107508A (en) Herbicidal composition
JPH05229908A (en) Herbicide composition for paddy field

Legal Events

Date Code Title Description
WAP Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1)