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`Application number: 1816459.0
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`

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`
` we
`
`ellectual
`Int
`Property
`Office
`
`Patents Form 1
`Patents Act 1977 (Rule 72)
`
`Request for grant of a patent
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`1200303573
`1018026659 D02093
`09/10/2018 210.00 DepositAccount
`
`Concept House
`Cardiff Road
`Newport
`South Wales
`NP10 8QQ
`
`Application number
`1. Your reference
`
`GB 1816459.0
`
`2.
`
`Full name, address and postcode of the applicant or of
`each applicant
`
`81698-GB-REG-ORG-NAT-1
`
`SYNGENTA PARTICIPATIONS AG
`Schwarzwaldallee 215
`Basel 4058
`08290835001
`Switzerland
`
`Patents ADP number (if you know it)
`IMPROVEMENTSIN OR RELATING TO ORGANIC
`3. Title of the invention
`COMPOUNDS
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`4. Nameof your agent(if you have one)
`“Address for service" to which all correspondence should
`be sent. This may be in the European Economic area or
`Channel Islands (see warning note below)
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`5. Priority declaration: Are you claiming priority from one or
`more earlier-filed patent applications? If so, please give
`details of the application(s)
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`SYNGENTALIMITED
`Jealott's Hill International Research Centre
`Bracknell RG42 6EY
`Berkshire
`United Kingdom
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`11797537001
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`Patents Form 1
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`pages of each item accompanying this form.
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`Continuation sheets of this form
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`Description:
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`36
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`Clainys):
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`Abstract:
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`4
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`1
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`11. IAWe request the grant of a patent on the basis of this application.
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`Signature: Subject: Christopher Andrews 27278;
`Issuer: European Patent Office, European
`Patent Office CA G2
`
`Date:
`
`09 Oct 2018
`
`12. Name, e-mail address, telephone, fax and/or mobile
`number, if any, of a contact point for the applicant
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`Andrews, MR Christopher John
`Email: global.patents@syngenta.com
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`Warning
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`invention should be prohibited or restricted under section 22 of the Patents Act 1977. You will be informed if it is necessary to
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`

`

`IMPROVEMENTS IN OR RELATING TO ORGANIC COMPOUNDS
`
`The present
`
`invention
`
`relates
`
`to
`
`novel
`
`herbicidal
`
`cyclohexanedione
`
`compounds,
`
`to processes for their preparation,
`
`to herbicidal compositions which
`
`comprise the novel compounds, and to their use for controlling weeds.
`
`Herbicidal cyclic dione compounds substituted by a phenyl which has an
`
`alkynyl-containing substituent are disclosed in, for example, WO2014/096289 and
`
`W0O2015/197468. The present invention relates to novel herbicidal cyclohexanedione
`
`10
`
`derivatives with improved properties.
`
`Thus, according to the present invention there is provided a compound of
`
`Formula (I)
`
`OR,
`
`XL
`0 R
`(I)
`
`G
`
`wherein
`
`R' is methyl;
`
`R? is methyl or methoxy;
`
`R* is methyl or methoxy;
`
`15
`
`20
`
`25
`
`R* is selected from the group consisting of C1-C4alkyl, C1-Csalkoxy-, C:-
`
`
`C,haloalkyl, -S(Q)nCi-Cealkyl,=--C(Q)Ci-Caalkyl, -C(O)Ci-Cahaloalkyl,
`
`
`S(O)nC1-Cehaloalkyl,
`-S(O)n-(CH2)n-Cs-Cecycloalkyl,
`-S(O),C(R™)R'R"°,
`C(O)H, -C(O)-(CH2)n-C3-Cecycloalkyl, -C(O)C(R"")R'2R18, -C(O)C2-Caalkenyl, -
`
`C(O)(CR®R"°)CN,
`
`-C(O)OC1-Cealkyl,
`
`-C(O)OC;-Cehaloalkyl,
`
`-
`
`30
`
`C(O)(CH2)nS(O)nC1-Cealkyl, -C(O)C1-CsalkoxyC1-Cealkyl, -C(O)NR®°R®, -C(O)-
`(CH2)n-NR’C(O)R8, -CN, -(CH2)n-phenyl, -C(O)-(CHz)n-phenyl, -S(O)n-(CH2)n-
`
`phenyl,
`
`-heterocyclyl,
`
`-C(O)-(CHz2)n-heterocyclyl,
`
`-S(O)n-(CHz2)n-heterocyclyl,
`
`

`

`wherein each heterocyclyl is a 5- or 6- membered heterocyclyl which may be
`
`aromatic, saturated or partially saturated and can contain from 1
`
`to 4
`
`heteroatoms each independently selected from the group consisting of
`
`oxygen, nitrogen and sulphur, and wherein said heterocyclyl or phenyl groups
`
`are optionally substituted by one,
`
`two or three substituents independently
`
`selected from the group consisting of C:-Csalkyl, C:1-Cshaloalkyl, C;-Csalkoxy,
`
`C2-Caalkenyl, C2-Csalkynyl, halogen, cyano andnitro;
`
`R® is selected from the group consisting of hydrogen and C,-Ce alkyl;
`
`10
`
`R® is selected from the group consisting of hydrogen, C:-Ce alkyl, C1-Ce
`
`alkoxy, C3-Cez cycloalkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are
`
`optionally substituted by one,
`
`two or
`
`three substituents
`
`independently
`
`selected from the group consisting of C:-C3 alkyl, C1-C3 haloalkyl, Ci-Cs
`
`15
`
`alkoxy, C2-Cs alkenyl, C2-Cs alkynyl, halogen, cyano and nitro; or
`
`R° and R® together form —CH2CH20CH2CH>2-; and
`
`R’is selected from the group consisting of hydrogen and C.-Ce alkyl:
`
`20
`
`R® is selected from the group consisting of hydrogen, C1-Ce alkyl, Ci-Ce
`
`alkoxy, C3-Cez cycloalkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are
`
`optionally substituted by one,
`
`two or
`
`three substituents
`
`independently
`
`selected from the group consisting of Ci-C3 alkyl, C1-C3 haloalkyl, Ci-Cs
`
`25
`
`alkoxy, C2-Cs3 alkenyl, C2-Cs alkynyl, halogen, cyano and nitro;
`
`R® is hydrogen or methyl;
`
`R'° is hydrogen or methyl; or
`
`30
`
`R® and R"° together form —CH2CH2-; and
`
`R"'' is hydrogen or methy!:
`
`35
`
`R'? and R'* together form —CH2-X-CH>2-;
`
`X is selected from the group consisting of O, S and N-R";
`
`

`

`wo
`
`R"* is selected from the group consisting of hydrogen, C1-Csalkyl and C1-Cs
`
`alkoxy-;
`
`G is selected from the group consisting of hydrogen, -(CHz)n-R*, -C(O)-R?, -
`
`C(O)-(CRfER4),-O-R®, -C(O)NR®R2, -S(O)2-R? and C1-Cgalkoxy-C;-Csalkyl-;
`
`R* is independently selected from the group consisting of hydrogen, Ci-
`
`Cealkyl,
`
`C1-C3haloalkyl,
`
`C2Csalkenyl,
`
`C2-Cealkynyl,
`
`Cs3-Cecycloalkyl,
`
`10
`
`heterocyclyl and phenyl wherein said heterocyclyl and phenyl groups are
`
`optionally substituted by one,
`
`two or
`
`three substituents
`
`independently
`
`selected from the group consisting of C1-Caalkyl, C1-Cshaloalkyl, C1-Csalkoxy,
`
`C2-C3alkenyl, C2-Csalkynyl, halogen, cyano and nitro;
`
`15
`
`R® is selected from the group consisting of C:-Csalkyl, C:-Cshaloalkyl, C2-
`
`Cealkenyl, C2-Cgalkynyl, Cs-Ce cycloalkyl, heterocyclyl and phenyl wherein
`
`said heterocyclyl and phenyl groups are optionally substituted by one, two or
`
`three substituents independently selected from the group consisting of C:-
`
`Caalkyl, Ci-Cshaloalkyl, Ci-C3alkoxy, C2-Csalkenyl, C2-Csalkynyl, halogen,
`
`20
`
`cyano and nitro;
`
`R° is hydrogen or C1-C3alkyl;
`
`R¢ is hydrogen or C,-C3 alkyl; and
`
`nis independently 0, 1 or 2;
`
`or an agriculturally acceptable salt thereof.
`
`Alkyl groups (e.g C:-Cealkyl) include, for example, methyl (Me, CHs), ethyl (Et,
`
`C2Hs), n-propyl (n-Pr), isopropyl (/-Pr), n-butyl (7-Bu), isobutyl (Bu), sec-butyl (s-Bu)
`
`and tert-butyl (¢-Bu).
`
`Alkenyl and alkynyl moieties can be in the form of straight or branched
`
`chains, and the alkenyl moieties, where appropriate, can be of either the (&)- or
`
`25
`
`30
`
`35
`
`

`

`(Z)-configuration.
`
`Examples are vinyl, allyl and propargyl. Alkenyl and alkynyl
`
`moieties can contain one or more double and/ortriple bonds in any combination.
`
`Halogen (or halo) encompasses fluorine, chlorine, bromine or iodine. The
`
`same correspondingly applies to halogen in the context of other definitions, such as
`
`haloalkyl.
`
`Haloalkyl groups
`
`(e.g Ci-C4haloalkyl)
`
`are,
`
`for example,
`
`fluoromethyl,
`
`difluoromethyl,
`
`trifluoromethyl, chloromethyl, dichloromethyl,
`
`trichloromethyl, 2,2,2-
`
`10
`
`trifluoroethyl,
`
`2-fluoroethyl,
`
`2-chloroethyl,
`
`pentafluoroethyl,
`
` 1,1-difluoro-2,2,2-
`
`trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl.
`
`Alkoxy groups (e.g C:-C4alkoxy-) are, for example, methoxy, ethoxy, propoxy,
`
`isopropoxy, n-butoxy,
`
`isobutoxy, sec-butoxy or tert-butoxy, preferably methoxy and
`
`15
`
`ethoxy.
`
`Alkoxyalkyl groups
`
`(e.g Ci-Cealkoxy-C:-Csalkyl-)
`
`includes,
`
`for example,
`
`methoxymethyl, methoxyethyl,
`
`ethoxymethyl,
`
`ethoxyethyl,
`
`n-propoxymethyl,
`
`n-
`
`propoxyethyl, isopropoxymethyl or isopropoxyethyl.
`
`Cycloalkyl groups (e.g C3-Cecycloalkyl-) include, for example cyclopropyl (c-
`
`propyl, c-Pr), cyclobutyl
`
`(c-butyl, c-Bu), cyclopentyl
`
`(c-pentyl) and cyclohexyl
`
`(c-
`
`hexyl) and may be substituted or unsubstituted as indicated.
`
`C,-Cealkyl-S-
`
`(alkylthio)
`
`is,
`
`for example, methylthio, ethylthio, propylthio,
`
`isopropylthio, n-butylthio,
`
`isobutylthio,
`
`sec-butylthio or
`
`tert-butylthio, preferably
`
`methylthio or ethylthio.
`
`20
`
`25
`
`C:-Cealkyl-S(O)-
`
`(alkylsulfinyl)
`
`is,
`
`for example, methylsulfinyl, ethylsulfinyl,
`
`30
`
`propylsulfinyl,
`
`isopropylsulfinyl, n-butylsulfinyl,
`
`isobutylsulfinyl,
`
`sec-butylsulfinyl or
`
`tert-butylsulfinyl, preferably methylsulfinyl or ethylsulfinyl.
`
`C,-Cealkyl-S(O)2- (alkylsulfonyl) is, for example, methylsulfonyl, ethylsulfonyl,
`
`propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl or
`
`35
`
`tert-butylsulfonyl, preferably methylsulfonyl or ethylsulfonyl.
`
`

`

`Heterocyclyl
`
`is a 5- or 6- membered heterocyclyl which may be aromatic,
`
`saturated or partially saturated and can contain from 1
`
`to 4 heteroatoms each
`
`independently selected from the group consisting of oxygen, nitrogen and sulphur.
`
`The invention also relates agriculturally acceptable salts of the compounds of
`
`Formula (I). Such salts include those which are able to form with amines, alkali metal
`
`and alkaline earth metal bases or quaternary ammonium bases. Among the alkali
`
`metal and alkaline earth metal hydroxides as salt formers, special mention should be
`
`made of the hydroxides of lithium, sodium, potassium, magnesium and calcium, but
`
`10
`
`especially the hydroxides of sodium and potassium. The compounds of Formula (I)
`
`according to the invention also include hydrates which may be formed during the salt
`
`formation.
`
`Examples of amines suitable for ammonium salt formation include ammonia
`
`15
`
`
`
`
`
`
`as secondary§andwell as primary, tertiary Cui-Cisalkylamines, Cu:-
`
`
`
`
`
`
`
`
`
`Cahydroxyalkylamines
`
`and Cz2-Cyalkoxyalkylamines,
`
`for example methylamine,
`
`ethylamine,
`
`n-propylamine,
`
`isopropylamine,
`
`the four butylamine
`
`isomers,
`
`n-
`
`amylamine,
`
`isoamylamine,
`
`hexylamine,
`
`heptylamine,
`
`octylamine,
`
`nonylamine,
`
`decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine,
`
`20
`
`methylethylamine, methylisopropylamine, methylhexylamine, methylnonylamine,
`
`methylpentadecylamine, methyloctadecylamine, ethyloutylamine, ethylheptylamine,
`
`ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-
`
`n-propylamine, diisopropylamine, di-n-butylamine, di-n-amylamine, diisoamylamine,
`
`dihexylamine,
`
`diheptylamine,
`
`dioctylamine,
`
`ethanolamine,
`
`n-propanolamine,
`
`25
`
`isopropanolamine, NV,N-diethanolamine, N-ethylpropanclamine, A/-butylethanolamine,
`
`allylamine,
`
`n-but-2-enylamine,
`
`n-pent-2-enylamine,
`
`2,3-dimethylbut-2-enylamine,
`
`dibut-2-enylamine,
`
`n-hex-2-enylamine,
`
`propylenediamine,
`
`trimethylamine,
`
`triethylamine,
`
`tri-n-propylamine,
`
`triisopropylamine, tri-n-butylamine,
`
`triisobutylamine,
`
`
`
`tri-sec-butylamine, and_ethoxyethylamine; tri-n-amylamine, methoxyethylamine
`
`
`
`30
`
`heterocyclic amines,
`
`for example pyridine, quinoline,
`
`isoquinoline, morpholine,
`
`piperidine, pyrrolidine,
`
`indoline, quinuclidine and azepine; primary arylamines, for
`
`example
`
`anilines, methoxyanilines,
`
`ethoxyanilines,
`
`o-, m-
`
`and_ p-toluidines,
`
`phenylenediamines, benzidines, naphthylamines and o-, m- and p-chloroanilines; but
`
`especially triethylamine, isopropylamine and diisopropylamine.
`
`35
`
`In one embodimentof the present invention R? is methyl.
`
`

`

`In one embodiment of the present invention R° is methyl.
`
`In another embodiment of the present invention R° is methoxy.
`
`In one embodiment of the present invention R? is methyl and R* is methyl.
`
`In one embodimentof the present invention R? is methyl and R* is methoxy.
`
`In one embodimentof the present invention R? is methoxy and R* is methoxy.
`
`10
`
`In one embodiment of the present invention, R* is C:-Czalkoxy- (e.g methoxy
`
`or ethoxy).
`
`In another embodiment of the present invention R* is -C(O)C1-Caalkyl (e.g —
`
`15
`
`C(O)methyl, —C(O)ethyl, —C(O)/-propyl) or —-C(O)tbutyl).
`
`In another embodiment of the present invention, R* is -C(O)C1-Cshaloalkyl,
`
`more preferably -C(O)C.-C2fluoroalkyl e.g -C(O)CHeaF, -C(O)CHFa2, -C(O)CFs).
`
`20
`
`In one embodiment of the present invention, R*is -S(O)nC1-Cealkyl especially
`
`—S(O)2methyl or —S(O)zethy!
`
`In
`
`another
`
`embodiment
`
`R*
`
`is
`
`-S(O)nCi-Cehaloalkyl,
`
`for
`
`example
`
`-
`
`S(O)echloromethyl.
`
`25
`
`In another embodiment R* is -S(O)n-(CHz)n-C3-Cecycloalkyl,
`
`for example -
`
`S(O)2-(CHz2)-c-propyl or, where n is O, -C3-Cecycloalkyl (for example cyclopropyl).
`
`In another embodiment of the present
`
`invention, R* is -C(O)OC:-Cealkyl,
`
`30
`
`especially -C(O)-O-methyl.
`
`In another embodimentof the present invention, R* is -S(O)nC(R™)R'2R"® or -
`
`C(O)C(R"")R'"R'? wherein R"' is hydrogen or methyl and R'*R‘* taken together are —
`
`CH20CH>2- (oxetan-3-yl).
`
`35
`
`In another embodiment of the present
`
`invention, R* is
`
`-C(O)-(CH2)n-Cs-
`
`Cecycloalkyl, for example -C(O)-c-propyl or -C(O)-(CHz2)-c-propyl.
`
`

`

`In another embodiment of the present invention, R* is -C(O)(CR°R")CN, for
`
`example -C(O)CH2CN, -C(O)CH(CHs)CN or -C(O)C(CHs3)20N.
`
`In another embodiment of the present invention, R* is -C(O)(CH2)nS(O)nCi-
`
`Cealkyl, for example -C(O)CH2S(O)amethyl.
`
`In another embodiment of the present invention, R* is -C(O)Ci-CsalkoxyC.-
`
`Cealkyl, for example -C(O)CH2-O-CHs, -C(O)CH2CH2-O-CHs3 or -C(O)CH(CHs3)-O-CHs3.
`
`10
`
`In another embodiment of the present invention, R* is -C(O)NR°R®, especially
`
`wherein R® is hydrogen and R® is C1-Ce¢ alkyl e.g t-butyl.
`
`-C(O)-(CH2)n-
`invention, R* is
`the present
`In another embodiment of
`NR’C(O)R?®, for example -C(O)-(CH2)-NR’C(O)R® or -C(O)NR’C(O)R®, for example -
`
`15
`
`C(O)NHC(0)-ébutyl or -C(O)NHC(O)pyrid-2-yl.
`
`In another embodiment of the present invention, R* is selected from the group
`
`consisting of —phenyl, -C(©)-phenyl, -S(O)nphenyl wherein each phenyl is optionally
`
`20
`
`substituted as defined previously.
`
`In another embodiment of the present invention R* is heterocyclyl, -C(O)-
`
`heterocyclyl or -S(O),-heterocyclyl.
`
`In another embodiment, each aforementioned
`
`heterocyclyl
`
`is an aromatic heterocyclyl
`
`(i.e heteroaryl), more preferably selected
`
`25
`
`from the group consisting of furanyl, pyrrolyl,
`
`thiophenyl,
`
`imidazolyl, pyrazolyl,
`
`oxazolyl, isoxazolyl, thiazolyl, pyranyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and
`
`triazolyl more preferably selected from the group consisting of pyridyl, pyridazinyl,
`
`pyrimidinyl and pyrazinyl each of which is optionally substituted as defined
`
`previously.
`
`In another embodiment, each aforementioned heterocyclyl is a partially
`
`30
`
`saturated heterocyclyl, more preferably selected from the group consisting of
`
`imidazolinyl,
`
`isoxazolinyl and thiazolinyl each of which is optionally substituted as
`
`defined previously.
`
`In another embodiment, each aforementioned heterocyclyl is a
`
`saturated heterocyclyl more preferably selected from the group consisting of
`
`morpholinyl,
`
`tetrahydrofuryl and tetrahydropyranyl each of which is optionally
`
`35
`
`substituted as defined previously.
`
`

`

`In one embodiment of the present invention, G is selected from the group
`
`consisting of hydrogen, C:-Cealkyl (e.g methyl, ethyl, n-propyl, Hpropyl, n-butyl, t
`
`butyl, -C2-Cgalkenyl (e.g vinyl), C2-Cgalkynyl (€.g
`
`propargyl), -C(O)C.-Cgalkyl (more
`
`preferably -C(O)Ci-Cealkyl e.g -C(O)/-propyl and -C(O)butyl) and -C(O)-O-C:-
`
`Csalkyl
`
`(more preferably -C(O)-O-C:-Cealkyl e.g -C(O)-O-methyl).
`
`In a preferred
`
`embodiment, G is hydrogen.
`
`Depending on the nature of the substituents, compounds of Formula (I) may
`
`exist in different isomeric forms. When G is hydrogen, for example, compounds of
`
`10
`
`Formula (l) may exist in different tautomeric forms.
`
`This invention covers all such isomers and tautomers and mixtures thereof in
`
`all proportions. Also, when substituents contain double bonds, cis- and trans-isomers
`
`can exist. These isomers, too, are within the scope of the claimed compounds of the
`
`15
`
`Formula (lI). Compounds of Formula (I) may contain asymmetric centres and may be
`
`present as a single enantiomer, pairs of enantiomers in any proportion or, where
`
`more than one asymmetric centre are present, contain diastereoisomers in all
`
`possible ratios. Typically one of the enantiomers has enhanced biological activity
`
`comparedto the other possibilities.
`
`20
`
`The compounds of Formula (I) according to the invention can be used as
`
`herbicides by themselves, but
`
`they are generally formulated into herbicidal
`
`compositions using formulation adjuvants, such as carriers, solvents and surface-
`
`active agents (SFAs). Thus,
`
`the present
`
`invention further provides a herbicidal
`
`25
`
`composition comprising a herbicidal compound according to any one of the previous
`
`claims and an agriculturally acceptable formulation adjuvant. The composition can be
`
`in the form of concentrates which are diluted prior to use, although ready-to-use
`
`compositions can also be made. Thefinal dilution is usually made with water, but can
`
`be made instead of, or in addition to, water, with, for example,
`
`liquid fertilisers,
`
`30
`
`micronutrients, biological organisms, oil or solvents.
`
`The herbicidal compositions generally comprise from 0.1 to 99 % by weight,
`
`especially from 0.1 to 95 % by weight, compounds of Formula (Il) and from 1
`
`to
`
`99.9 % by weight of a formulation adjuvant which preferably includes from 0 to 25 %
`
`35
`
`by weight of a surface-active substance.
`
`

`

`The compositions can be chosen from a numberof formulation types, many
`
`of which are known from the Manual on Development and Use of FAO Specifications
`
`for Plant Protection Products, 5th Edition, 1999. These include dustable powders
`
`(DP), soluble powders (SP), water soluble granules (SG), water dispersible granules
`
`(WG), wettable powders
`
`(WP), granules (GR)
`
`(slow or fast
`
`release),
`
`soluble
`
`concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (UL), emulsifiable
`
`concentrates (EC), dispersible concentrates (DC), emulsions (both oil
`
`in water (EVV)
`
`and water in oil
`
`(EO)), micro-emulsions (ME), suspension concentrates (SC),
`
`aerosols, capsule suspensions
`
`(CS) and seed treatment
`
`formulations.
`
`The
`
`10
`
`formulation type chosen in any instance will depend upon the particular purpose
`
`envisaged and the physical, chemical and biological properties of the compound of
`
`Formula (I).
`
`Dustable powders (DP) may be prepared by mixing a compound of Formula
`
`(1) with one or more solid diluents (for example natural clays, kaolin, pyrophyllite,
`
`15
`
`bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium
`
`phosphates, calcium and magnesium carbonates, sulphur, lime, flours, talc and other
`
`organic and inorganic solid carriers) and mechanically grinding the mixture to a fine
`
`powder.
`
`Soluble powders (SP) may be prepared by mixing a compound of Formula (I)
`
`20
`
`with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium
`
`carbonate or magnesium sulphate) or one or more water-soluble organic solids (such
`
`as a polysaccharide) and, optionally, one or more wetting agents, one or more
`
`dispersing agents or a mixture of said agents to improve water dispersibility/solubility.
`
`The mixture is then ground to a fine powder. Similar compositions may also be
`
`25
`
`granulated to form water soluble granules (SG).
`
`Wettable powders (WP) may be prepared by mixing a compound of Formula
`
`(l} with one or more solid diluents or carriers, one or more wetting agents and,
`
`preferably, one or more dispersing agents and, optionally, one or more suspending
`
`agents to facilitate the dispersion in liquids. The mixture is then ground to a fine
`
`30
`
`powder.
`
`Similar compositions may also be granulated to form water dispersible
`
`granules (WG).
`
`Granules (GR) may be formed either by granulating a mixture of a compound
`
`of Formula (I) and one or more powdered solid diluents or carriers, or from pre-
`
`formed blank granules by absorbing a compound of Formula (I) (or a solution thereof,
`
`35
`
`in a suitable agent) in a porous granular material (such as pumice, attapulgite clays,
`
`

`

`10
`
`fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing
`
`a compound of Formula (I) (or a solution thereof,
`
`in a suitable agent) on to a hard
`
`core material (such as sands, silicates, mineral carbonates, sulphates or phosphates)
`
`and drying if necessary. Agents which are commonly used to aid absorption or
`
`adsorption include solvents (such as aliphatic and aromatic petroleum solvents,
`
`alcohols, ethers, ketones and esters) and sticking agents (such as polyvinyl acetates,
`
`polyvinyl alcohols, dextrins, sugars and vegetable oils). One or more other additives
`
`may also be included in granules (for example an emulsifying agent, wetting agent or
`
`dispersing agent).
`
`10
`
`Dispersible Concentrates (DC) may be prepared by dissolving a compound of
`
`Formula (I) in water or an organic solvent, such as a ketone, alcohol or glycol ether.
`
`These solutions may contain a surface active agent (for example to improve water
`
`dilution or prevent crystallisation in a spray tank).
`
`Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) may be
`
`15
`
`prepared by dissolving a compound of Formula (I) in an organic solvent (optionally
`
`containing one or more wetting agents, one or more emulsifying agents or a mixture
`
`of said agents).
`
`Suitable organic solvents for use in ECs
`
`include aromatic
`
`hydrocarbons
`
`(such as
`
`alkylbenzenes or alkylnaphthalenes,
`
`exemplified
`
`by
`
`SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a
`
`20
`
`Registered Trade Mark), ketones (Such as cyclohexanone or methylcyclohexanone)
`
`and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N-alkylpyrrolidones
`
`(such as N-methylpyrrolidone or N-octylpyrrolidone), dimethyl amides of fatty acids
`
`(such as Cgs-Cio fatty acid dimethylamide) and chlorinated hydrocarbons. An EC
`
`product may spontaneously emulsify on addition to water, to produce an emulsion
`
`25
`
`with sufficient stability to allow spray application through appropriate equipment.
`
`Preparation of an EW involves obtaining a compound of Formula (I) either as
`
`a liquid (if it is not a liquid at room temperature,
`
`it may be melted at a reasonable
`
`temperature,
`
`typically below 70°C) or in solution (by dissolving it
`
`in an appropriate
`
`solvent) and then emulsifying the resultant liquid or solution into water containing one
`
`30
`
`or more SFAs, under high shear, to produce an emulsion. Suitable solvents for use
`
`in EWsinclude vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes),
`
`
`
`aromatic solvents and_other(such as alkylbenzenes or alkylnaphthalenes)
`
`
`
`
`
`appropriate organic solvents which have a low solubility in water.
`
`Microemulsions (ME) may be prepared by mixing water with a blend of one or
`
`35
`
`more
`
`solvents with
`
`one
`
`or more
`
`SFAs,
`
`to
`
`produce
`
`spontaneously
`
`a
`
`

`

`11
`
`thermodynamically stable isotropic liquid formulation. A compound of Formula (I) is
`
`presentinitially in either the water or the solvent/SFA blend. Suitable solvents for
`
`use in MEs include those hereinbefore described for use in in ECs or in EWs. An ME
`
`may be either an oil-in-water or a water-in-oil system (which system is present may
`
`be determined by conductivity measurements) and may be suitable for mixing water-
`
`soluble and oil-soluble pesticides in the same formulation. An ME is suitable for
`
`dilution into water, either remaining as a microemulsion or forming a conventional oil-
`
`in-water emulsion.
`
`Suspension concentrates (SC) may comprise aqueous or non-aqueous
`
`10
`
`suspensions of finely divided insoluble solid particles of a compound of Formula (I).
`
`SCs may be prepared by ball or bead milling the solid compound of Formula (I) in a
`
`suitable medium, optionally with one or more dispersing agents, to produce a fine
`
`particle suspension of the compound. One or more wetting agents may be included
`
`in the composition and a suspending agent may be included to reduce the rate at
`
`15
`
`which the particles settle. Alternatively, a compound of Formula (Il) may be dry milled
`
`and added to water, containing agents hereinbefore described,
`
`to produce the
`
`desired end product.
`
`Aerosol formulations comprise a compound of Formula (I) and a suitable
`
`propellant (for example n-butane). A compound of Formula (I) may also be dissolved
`
`20
`
`or dispersed in a suitable medium (for example water or a water miscible liquid, such
`
`as n-propanol) to provide compositions for use in non-pressurised, hand-actuated
`
`spray pumps.
`
`Capsule suspensions (CS) may be prepared in a manner similar to the
`
`preparation of EW formulations but with an additional polymerisation stage such that
`
`25
`
`an aqueous dispersion of oil droplets is obtained,
`
`in which each oil droplet
`
`is
`
`encapsulated by a polymeric shell and contains a compound of Formula (I) and,
`
`optionally, a carrier or diluent therefor. The polymeric shell may be produced by
`
`either an interfacial polycondensation reaction or by a coacervation procedure. The
`
`compositions may provide for controlled release of the compound of Formula (I) and
`
`30
`
`they may be used for seed treatment. A compound of Formula (Il) may also be
`
`formulated in a biodegradable polymeric matrix to provide a slow, controlled release
`
`of the compound.
`
`The composition may include one or more additives to improve the biological
`
`performance of the composition,
`
`for example by improving wetting,
`
`retention or
`
`35
`
`distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility
`
`

`

`12
`
`of a compound of Formula (I). Such additives include surface active agents (SFAs),
`
`spray additives based on oils, for example certain mineral oils or natural plant oils
`
`(such as soy bean and rape seed oil), and blends of these with other bio-enhancing
`
`adjuvants (ingredients which may aid or modify the action of a compound of Formula
`
`(I).
`
`Wetting agents, dispersing agents and emulsifying agents may be SFAs of
`
`the cationic, anionic, amphoteric or non-ionic type.
`
`Suitable SFAs of the cationic type include quaternary ammonium compounds
`
`(for example cetyltrimethyl ammonium bromide), imidazolines and amine salts.
`
`10
`
`Suitable anionic SFAs_
`
`include alkali metals salts of fatty acids, salts of
`
`aliphatic monoesters of sulphuric acid (for example sodium lauryl sulphate), salts of
`
`sulphonated aromatic compounds (for example sodium dodecylbenzenesulphonate,
`
`calcium dodecylbenzenesulphonate, butylnaphthalene sulphonate and mixtures of
`
`sodium di-/sopropyl- and tri-isopropyl-naphthalene sulphonates), ether sulphates,
`
`15
`
`alcohol ether sulphates (for example sodium laureth-3-sulphate), ether carboxylates
`
`(for example sodium laureth-3-carboxylate), phosphate esters (products from the
`
`reaction between one or more fatty alcohols and phosphoric acid (predominately
`
`mono-esters) or phosphorus pentoxide (predominately di-esters), for example the
`
`reaction between lauryl alcohol and tetraphosphoric acid; additionally these products
`
`20
`
`may be ethoxylated), sulphosuccinamates, paraffin or olefine sulphonates, taurates
`
`and lignosulphonates.
`
`Suitable SFAs of the amphoteric type include betaines, propionates and
`
`glycinates.
`
`Suitable SFAs of the non-ionic type include condensation products of alkylene
`
`oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof,
`
`with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such
`
`as octylphenol, nonylphenol or octylcresol); partial esters derived from long chain
`
`fatty acids or hexitol anhydrides; condensation products of said partial esters with
`
`ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide);
`
`alkanolamides; simple esters (for example fatty acid polyethylene glycol esters);
`
`amine oxides (for example lauryl dimethyl amine oxide); and lecithins.
`
`Suitable
`
`suspending
`
`agents
`
`include
`
`hydrophilic
`
`colloids
`
`(such
`
`as
`
`polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose) and swelling
`
`clays