Title of Invention

BIPHENYL DERIVATIVES,

Abstract "Biphenyl derivatives, a composition comprising them and its application as a fungicide" A fungicidally active compound of formula (I): where Het is a substituted 5- or 6-membered heterocyclic ring; R1 is hydrogen, formyl, CO-C1-4 alkyl, COO C1-4 alkyl, C1-4alkoxy(C1-4)alkylene, CO-C1-4 alkylenoxy(C1-4kyl, propargyl or allcuyl; R2 R3R4and R5are each, independently, hydrogen, halogen, methyl or CF3; each R6, independently, halogen, methyl or CF3; R7is (Z),C=(Y1 (Z)m(y1-C(Y2(Y3 or lri(C].4)alkylsilyl; X is O or S; Y1,Y2 And Y3e each, independently, hydrogen, halogen, C1-6 alyl [optionally substituted by one or more substituents each independently selected from halogen, hydroxy, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 alkylthio, C1-4 haloalkylthio, C1-4 alkylamino, di(C1-4)alkylamino, C1-4alkoxycarbonyl, Ci.4alkylcarbonyloxy and tri(C1- 4)alkylsily]], C2-4 alkenyl [optionally substituted by one or more substituents each intlepcndently selected from halogen], C2-4 alkynyl [optionally substituted by one or more substituents each independently selected from halogen], C3-7 cycloalkyl [optionally substituted by one or more substituents each independently selected from halogen, C1-4 alkyl and C1-4 haloalkyl] or tri(C1-4)alkylsilyl; Z is C1-4 alkylene [optionally substituted by one or more substituents each independently selected from hydroxy, cyano, C1-4 alkoxy, halogen, C1-4 haloalkyl, C1-4 haloalkoxy, C1-4 alkylthio, COOH and COO-C1-4 alkyl]; m is 0 or 1; and n is 0, 1 or 2; the invention also relates to novel intermediates used in the preparation of these compounds, to agrochemical compositions which comprise at least one of the novel compounds as active ingredient and to the use of the active ingredients or compositions in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.
Full Text

The present invention relates to biphenyl derivatives, a composition comprising them and its application as a fungicide.
The present invention relates to novel carboxamide derivatives as active ingredients which have microbicidal activity, in particular fungicidal acitivity. The invention also relates to preparation of these active ingredients, to novel diphenyl derivatives used as intermediates in the preparation of these active ingredients, to preparation of these novel intermediates, to agrochemcial compositions which comprise at least one of the novel active ingredients, to preparation of these compositions and to use of the active ingredients or compositions in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.
Fungicidally active carboxamide derivatives are disclosed in JP2001072510, JP2001072508, JP2001072507 and JP2001302605.
Certain amino- or halo-substituted diphenyl derivatives are disclosed in DE2205732 andJP2001302605.
The present invention provides a compound of formula (I):


substituted by one or more substituents each independently selected from halogen, hydroxy, C]-4 alkoxy. CM haloalkoxy, CM alkylthio, CM haloalkylthio, CM alkylamino, di(CM)alkylamino, CM alkoxycarbonyl, CM alkylcarbonyloxy and tri(CM)alkylsilyl], C2-4 alkenyl [optionally substituted by one or more substituents each independently selected from halogen], C2-4 alkynyl [optionally substituted by one or more substituents each independently selected from halogen], Cs.y cycloalkyl [optionally substituted by one or more substituents each independently selected from halogen. CM alkyl and CM haloalkyl] or tri(CM)alkylsilyl; Z is CM alkylene [optionally substituted by one or more substituents each independently selected from hydroxy, cyano. CM alkoxy, halogen, CM haloalkyl. CM haloalkoxy. CM alkylthio, COOH and COO-CM alkyl]; m is 0 or 1; and n is 0, 1 or 2.
In one particular aspect, the present invention provides a compound of formula (I) as defined above where Y1 Y2 and Y3 are each, independently, hydrogen, halogen. CM alkyl [optionally substituted by one or more substituents each independently selected from halogen, hydroxy, CM alkoxy, C1-4 haloalkoxy, C1-4 alkylthio, CM haloalkylthio, C1-4 alkylamino, di(C]-4)alkylamino, C 1-4 alkoxycarbonyl and tri(Ci.4)alkylsilyl], C2-4 alkenyl [optionally substituted by one or more substituents each independently selected from halogen], C2-4 alkynyl [optionally substituted by one or more substituents each independently selected from halogen], C3.7 cycloalkyl [optionally substituted by one or more substituents each independently selected from halogen. CM alkyl and CM haloalkyl] or tri(C]-4)alkylsilyl.
In one aspect, the present invention provides a compound of formula (I) as defined above where Z is CM alkylene [optionally substituted by one or more substituents each independently selected from hydroxy, cyano, C1-4 alkoxy, CM haloalkoxy, C1-4 alkylthio, COOH and COO-CM alkyl].


1
Each alkyl moiety is a straight or branched chain and is, for example, methyl, ethyl, n-propyl, n-butyl, iso-propyl, n-butyl, sec-butyl, iso-butyl or tert-butyl. Likewise, each alkylene moiety is a straight or branched chain.

Haloalkyl moieties are alkyl moieties which are substituted by one or more of the same or different halogen atoms and are, for example, CF3, CF2CI, CHF2, CH2F, CCI3, CF3CH2, CHF2CH2, CH2FCH2, CH3CHF or CH3CF2.
Alkenyl and alkynyl moieties can be in the form of straight or branched chains. The alkenyl moieties, where appropriate, can be of either the (E)- or (Z)-conf]guration. Examples are vinyl, allyl, ethynyl and propargyl.
Cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.
In tri(CM)a]kylsilyl and in di(CM)alkylamino, each alkyl moiety is selected independently.
Throughout this description, Me stands for methyl and Et stands for ethyl.
It is preferred that Het is pyrazole, pyrrole, thiophene, furan, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, 5.6-dihydropyran or 5.6-dihydro-L4-oxathiine [more preferably pyrazole, pyrrole, thiophene, furan, thiazole, oxazole, pyridine, pyrimidine, pyridazine or 5.6-dihydropyran; yet more preferably pyrazole, pyrrole, pyridine or thiazole; and even more preferably pyrazole, pyrrole or thiazole].
In one aspect it is preferred that Het is pyrazole, pyrrole, thiophene, furan, thiazole, isothiazole, oxazole, isoxazole, pyrazine, pyrimidine, pyridazine, 5.6-dihydropyran or 5.6-dihydro-1.4-oxathiine [more preferably pyrazole, pyrrole, thiophene, furan, thiazole, oxazole, pyrimidine, pyridazine or 5.6-dihydropyran and even more preferably pyrazole, pyrrole or thiazole].


C2-4 haloalkenyl or C3-6 cycloalkyl (optionally substituted by one or more substituents each independently selected from halogen and C1-2 alkyl).
Preferably Z is C1-2 alkylene [which may be optionally substituted by one or more substituents each independently selected from halogen. CM haloalkyl and CM haloalkoxy].
Preferably R is in the 4' position.
Preferably R^ is vinyl [optionally substituted by one to three substituents each independently selected from halogen, CM alkyl, C1-3 haloalkyl, C3-6 cycloalkyl (optionally substituted by one to five substituents each independently selected from halogen, CH3 and C1-2 haloalkyl) andtrimethylsilyl], ethynyl [optionally substituted by one substituent selected from cyclopropyl, cyclopentyl and cyclohexyl (each optionally substituted by one to five substituents each independently selected from halogen, CH3 and C]-2 haloalkyl), halogen, C1-6 alkyl, C1-4haloalkyl, C2-4 alkenyl, C2-4 haloalkenyl and tri(CM)alkylsilyl], allyl [optionally substituted by one to three substituents each independently selected from halogen, CH3, C1_2 haloalkyl andtrimethylsilyl], propargyl [optionally substituted by one to three substituents each independently selected from halogen. CM alkyl, C1-2 haloalkyl andtrimethylsilyl] or tri(Ci^)alkylsilyl.
In one particular aspect R is preferably vinyl [optionally substituted by one to three substituents each independently selected from halogen. CM alkyl, C1-3 haloalkyl, C3-6 cycloalkyl andtrimethylsilyl], ethynyl [optionally substituted by one substituent selected from halogen. CM alkyl, C1-2 haloalkyl, cyclopropyl (optionally substituted by one to five substituents each independently selected from halogen, CH3, C1-2 haloalkyl and trimethylsilyl) and trimethylsilyl], allyl [optionally substituted by one to three substituents each independently selected from halogen, CH3, C]-2 haloalkyl andtrimethylsilyl], propargyl [optionally substituted by one to three substituents each independently selected from halogen,
CH3, C]-2 haloalkyl andtrimethylsilyl] or tri(CM)alkylsilyl.

In another particular aspect R is preferably vmyl [optionally substituted by one to three
substituents each independently selected from halogen, CM alkyl, C1-3 haloalkyl, C3-6
cycloalkyl andtrimethylsilyl], ethynyl [optionally substituted by one substituent selected from
halogen. CM alkyl, C1-2 haloalkyl andtrimethylsilyl], allyl [optionally substituted by one to
three substituents each independently selected from halogen, CH3, C1-2 haloalkyl and
trimethylsilyl], propargyl [optionally substituted by one to three substituents each

independently selected from halogen, CH3, C1-2 haloalkyl and trimethylsilyl] or tri(C1-4)alkylsilyl.



preferably methyl or methoxymethylene; and most preferably methyl.
Preferably carbon atoms in the Het ring which are not bonded to the atom substituted by CXNR1 are, independently, either unsubstituted or substituted by Ry.

When Ry is a substituent on a carbon atom which is not bonded to the atom substituted by CXNR1 it is preferably halogen, C1-3 alkyl, C1-3 haloalkyl or methoxymethylene; more preferably chloro, methoxymethylene, CH3, CHF2 or CF3; yet more preferably chloro, CH3, CHF2 or CF3; and even more preferably CH3 or CF3.There may be one or two carbon atoms in the Het ring bonded to the atom substituted by CXNR1; preferably such carbon atoms are, independently, either unsubstituted or substituted by R^.
When R^ is a substituent on a carbon atom bonded to the atom substituted by CXNR^ it is preferably halogen, C1-3 alkyl or C1-3 haloalkyl; more preferably chloro, fluoro, bromo, C]_2 alkyl, CF3, CF2CI, CHF2, CH2F; and even more preferably chloro, fluoro, bromo, methyl, CF3, CHF2 or CH2F.
More preferably, when there is only one carbon atom in the Het ring bonded to the atom substituted by CXNR1 that carbon atom is substituted by Ry.
More preferably, when there are two carbon atoms in the Het ring bonded to the atom substituted by CXNR1 one such carbon atom is substituted by Ry and the other carbon atom is either unsubstituted or is substituted by fluoro, chloro or methyl.



are as defined above for a compound of formula (I). Many compounds of formula (in):
il
is bromo, chloro or iodo, are also novel and are useful as intermediates in the preparation of compounds of formula (I).
Certain compounds of formula (HI) are already known; Table 0 shows known



Preferably Hal is bromo or chloro.
More preferably Hal is bromo.
The compoimds of formulae (I), (II) and (UI) may exist as different geometric or optical isomers or in diflferent tautomeric forms. For each formula, this invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compotmds.
TTie compounds in Tables 1 to 13 below illustrate compounds of the invention.























Table 1 provides 287 compounds of formula (laD) wherein R\ R\ R^ R^, R^^ and X are as defined in Table 1.



Table 1 provides 287 compounds of formula (laE) wherein R1 , R7 , R8 , R9 , R10 and X are as defined in Table 1.
Table 1 provides 287 compounds of formula (laF) wherein R1R7, R8, R9, R10 and X are as defined in Table 1.
Table 1 provides 287 compounds of formula (laG) wherein R1 , R7 , R8 , R9 , R10 and X are as defined in Table 1.


Table 1 provides 287 compounds of formula (laH) wherein R\ R\ R^ R^ R'^ and X are as defined in Table 1.
Table 1 provides 287 compounds of formula (lal) wherein R1 R7 R8 R9 R10 and X are as defined in Table 1.
Table 1 provides 287 compounds of formula (laJ) wherein R1 R7, R8, R9, R10 and X are as defined in Table I.








































Table 3 provides 276 compounds of formula (IcD) wherein R1 R7, R9, R10 and X are as
tlcfined in Table 3 .


Table 3 provides 276 compounds of formula (IcE) wherein R1 R7, R9, R10 and X are as
(icfincd in Table 3 .
Fable 3 provides 276 compounds of formula (IcF) wherein R1 R7, R9, R10 and X are as
(defined in Table 3 .

Table 3 provides 276 compounds of formula (IcG) wherein R1 R7, R9, R10 and X are as
defined in Table 3 .


























Table 9 provides 212 compounds of formula (liB) wherein R1 R7 and R8 are as defined in Table 9.
1
Table 9 provides 212 compounds of formula (liC) wherein R , R7 and R8 are as defined in Table 9.
1 "7 R
Table 9 provides also 212 compounds of formula (liD) wherein R , R and R are as defined in Table 9.

Table 10 provides 14 compounds of formula (Ij):













Throughout this description, temperatures are given in degrees Celsius; "NMR" mcajis nuclear magnetic resonance spectrum; MS stands for mass spectrom; M*-l or M^-*-l are signals in the mass spectrum respectively corresponding to the molecular weight minus 1 or the molecular weight plus 1; and **%" is pncent by weight, tmless corresponding concentrations are indicated in other units.
The following abbreviations are used throughout this description:
m.p. = melting point b.p.« boiling point.
s = singlet br = broad
d *= doublet dd = doublet of doublets
t = triplet q « quartet
m = multiplei ppm - parts per million
Table 14 shows selected melting point, selected molecular ion and selected NMR ^y^rn, all with CDCI3 as the solvent (unless otherwise stated; if a mixture of solvents is present, this is indicated as, for example, (CDCh / d^-DMSO)), (no attempt is made to list all characterising data in dl cases) for compounds of Tables 1 to L3. Unless otherwise staled, the data relate to a cis/trans mixture of each compound.






















The compounds according to the present invention maybe prepared according to the following reaction schemes, in which, unless otherwise stated, the definition of each variable is as defined above for a compound of formula (I).
There are a number of alternative methods for preparing a compound of formula (I).


amine, an inorganic carbonate or a hydrogen carbonate]. Alternatively, if R" is a leaving group, the reaction is carried out in the presence of at least one equivalent of base [such as pyridine, a tertiary amine, an inorganic carbonate or a hydrogen carbonate].
Method C
A compound of formula (I) [where R1 is as defined above but is not hydrogen] may be prepared by reacting a compound of formula (I) [where R1 is hydrogen] with a compound of formula R1-L1 [where R1 is as defined above but is not hydrogen; and LMS a leaving group such as CI, Br, I, a sulfonate (for example a mesylate or a tosylate) or OC(0)CM alkyl] in a solvent [such as a halogenated solvent (for example dichloromethane), an ether, ethylacetate, DMF or even water (as a biphasic mixture, optionally in the presence of a phase transfer catalyst such as tetrabutylammonium hydrogensulfate)] and in the presence of a base [such as a tertiary amine, an alkali carbonate, an alkali bicarbonate, an alkali hydroxide or NaH; though if L1 is O(CO) C1-4 alkyl then simply heating without base is possible].
Method D
A compound of formula (I) maybe prepared by reacting a compound of formula (HI) [where Hal is preferably bromo or iodo] with a compound of formula Het-C(=0)NH2 in the presence of a Cu(I) compound and an aprotic solvent [such as a cyclic ether, for example dioxane] at an elevated temperature and preferably at reflux . The preferred conditions are Cul used at 2% to 100%mole/mole, relative to the compound of formula (HI), in the presence of a 1,2-diamine as a hgand-forming substance (such as 1,2-diamino cyclohexane or ethylene diamine) and at least 1 equivalent of a base (such as an alkali carbonate or an alkali phosphate. The article by A.Klapars et al. J.Am.Chem.Soc. 123,7727 (2001) provides details of analogous preparations.
Method E
A compound of formula (I) may be prepared by conversion of a compound of formula (IV)


[where FG is a functional group which is convertible to R7 in one or more synthetic steps]. Functional group ixiterconversions are standard procedures for a person skilled in the art. There arc many methods described in the literature, which can be used as such or with modifications according to the functionalities present; Table A gives h'terature references (some of which also cite further sppropriate references) which are specifically relevant to the preparation of a compound of formula (I) by the interconversion of FG to R7. It is apparent to the person skilled in the art that the literature samples given m Table A are not necessarily limited to the preparation of the specifically mentioned R7 but can be also applied by analogy to the preparation of other structurally related R7







A compound of formula (II), (HI) or (VI) may be prepared, by functional group interconversion, from a compound of formula (V) [where FG is as defined above for a compound of formula (IV) and T is either halogen, amino, NHR\ a protected amino group T' (for example a carbamate, an amide, a cyclic imide, an N-alkyl-, N-alkenyl-, N-benzyl-, N-diphenylmethyl- or N-trityl-derivative, an imine derivative or an N-silyl- or N-disilyl-derivative) or a group T" (that is, a group which may be converted to NH2 or NHR' by applying synthetic methodology described in the literature; T" being preferably azido, nitro, halogen, triflate, CONH2, COOH, COCl or NCO)]. Starting from a compound of formula (V) the functional group FG may be converted to R7 by applying a method analogous to method E above. This conversion leads directly to a compound of formula (E) [when T is NHRi], to a compound of formula (HI) [when T is halogen (preferably chloro, bromo or iodo)] or to a compoimd of formula (VI) [when T is T' or T"].
In a second step a compound of formula (VI) or (II) [when R1 is other than H] can be converted to a compound of formula (H) [where R1 is H] by either applying the methods [that is, deprotection or conversion of T" to NH2] as generically described above.

Examples of versatile values for T' plus methods for deprotection are given in T.W.Green and P.Wuts, Protective Groups in Organic Synthesis, 3rd edition (John Wiley & Sons 1999), Chapter 7.
Compilations of useful values for T" plus literature to convert T" into NH2, T' or NHR1 can be found in M.B. Smith, Compendium of Organic Synthetic Methods, Vols. 1-10, Chapter 7 (Wiley, Vol .10: 2002).

A compound of formula (11), (HI) or (VI) may be prepared by a coupling reaction between a compound of formula (VII) and a compound of formula (VHI) [where Ra and Ra' are each, independently, halogen (preferably CI, Br or I), triflate or a metal-containing functionality containing, for example, B, Sn, Mg, Zn or Cu as the metal; examples are B(0H)2, esters of boronic acid (preferably esters derived from 1,2- or 1,3-diols), trialkyltin (preferably Sn(CH3)3 or Sn(nBu)3), a halogen salt of Mg , a halogen salt of Zn or Cu. If either Ra or Ra' is a metal containing functionality, the other substituent must be halogen or triflate.
Such coupling reactions are widely known in the literature. Especially suitable are the Pd(0) ,Ni(0), or copper catalysed couplings which are well known to the person skilled in the art as Stille coupling, Suzuki coupling, Negishi coupling or UUmann reaction. A comprehensive review of these reactions can be found in Metal-Catalysed Cross-Coupling Reactions; F.Diederich and P.Stang (eds.); Wiley-VCH; Weinheim 1998.

I
In a second step a compound of fonnula (VI) or (H) [when R' is other than H] can be converted to a compound of formula (II) [where R' is H] by either applying the methods [that is, deprotection or conversion of T" to NH2] as generically described above.
Surprisingly, it has now been found that the novel compounds of formula (I) have, for practical purposes, a very advantageous spectrum of activities for protecting plants against diseases that are caused by fungi as well as by bacteria and viruses.
The compounds of formula (I) can be used in the agricultural sector and related fields of use as active ingredients for controlling plant pests. The novel compounds are distinguished by excellent activity at low rates of application, by being well tolerated by plants and by being environmentally safe. They have very useful curative, preventive and systemic properties and are used for protecting numerous cultivated plants. The compounds of formula I can be used to inhibit or destroy the pests that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time protecting also those parts of the plants that grow later e.g. from phytopathogenic microorganisms.
It is also possible to use compounds of formula (I) as dressing agents for the treatment of plant propagation material, in particular of seeds (fruit, tubers, grains) and plant cuttings (e.g. rice), for the protection against fungal infections as well as against phytopathogenic fungi occurring in the soil.
Furthermore the compounds according to present invention may be used for controlling fungi in related areas, for example in the protection of technical materials, including wood and wood related technical products, in food storage, in hygiene management, etc.
The compounds of formula (I) are, for example, effective against the phytopathogenic fungi of the following classes: Fungi imperfecti (e.g. Botrytis, Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora and Altemaria) and Basidiomycetes (e.g. Rhizoctonia, Hemileia, Puccinia). Additionally, they are also effective against the Ascomycetes classes (e.g. Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula) and of the Oomycetes classes (e.g. Phytophthora, Pythium, Plasmopara). Outstanding activity has been observed against powdery mildew (Erysiphe spp.) and rust (Puccinia spp.). Furthermore, the novel compounds of formula I are effective against phytopathogenic bacteria and viruses (e.g. against

Xanthomonas spp, Pseudomonas spp, Erwinia amylovora as well as against the tobacco mosaic virus).
Within the scope of present invention, target crops to be protected typically comprise the following species of plants: cereal (wheat, barley, rye, oat, rice, maize, sorghum and related species); beet (sugar beet and fodder beet); pomes, drupes and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, groundnuts); cucumber plants (pumpkins, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); citrus fruit (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); lauraceae (avocado, cinnamomum, camphor) or plants such as tobacco, nuts, coffee, eggplants, sugar cane, tea, pepper, vines, hops, bananas and natural rubber plants, as well as ornamentals.
The compounds of formula (I) are used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end they are conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances. As with the type of the compositions, the methods of application, such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances. The compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.
Suitable carriers and adjuvants can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are for example described in WO 97/33890.
The compounds of formula (I) are normally used in the form of compositions and can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds. These further compounds can be e.g. fertilizers or micronutrient donors or other preparations which influence the growth of plants. They can also be selective herbicides as

well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.
The compounds of formula (I) can be mixed with other fungicides, resulting in some cases in unexpected synergistic activities. Mixing components which are particularly preferred are azoles, such as azaconazole, BAY 14120, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, pefurazoate, penconazole, pyrifenox, prochloraz, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole; pyrimidinyl carbinole, such as ancymidol, fenarimol, nuarimol; 2-amino-pyrimidines, such as bupirimate, dimethirimol, ethirimol; morpholines, such as dodemorph, fenpropidine, fenpropimorph, spiroxamine, tridemorph; anilinopyrimidines, such as cyprodinil, mepanipyrim, pyrimethanil; pyrroles, such as fenpiclonil, fludioxonil; phenylamides, such as benalaxyl, furalaxyl, meta-laxyl, R-metalaxyl, ofurace, oxadixyl; benzimidazoles, such as benomyl, carbendazim, debacarb, fuberidazole, thiabendazole; dicarboximides, such as chlozolinate, dichlozoline, iprodione, myclozoline, procymidone, vinclozoline; carboxamides, such as carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, thifluzamide; guanidines, such as guazatine, dodine, iminoctadine; strobilurines, such as azoxystrobin, kresoxim-methyl, metominostrobin, SSF-129, trifloxystrobin, picoxystrobin, BAS 500F (proposed name pyraclostrobin), BAS 520; dithiocarbamates, such as ferbam, mancozeb, maneb, metiram, propineb, thiram, zineb, ziram; N-halomethylthiotetrahydrophthalimides, such as captafol, captan, dichlofluanid, fluoromides, folpet, tolyfluanid; Cu-compounds, such as Bordeaux mixture, copper hydroxide, copper oxychloride, copper sulfate, cuprous oxide, mancopper, oxine-copper; nitrophenol-derivatives, such as dinocap, nitrothal-isopropyl; organo-p-derivatives, such as edifenphos, iprobenphos, isoprothiolane, phosdiphen, pyrazophos, tolclofos-methyl; various others, such as acibenzolar-S-methyl, anilazine, benthiavalicarb, blasticidin-S, chinomethio-nate, chloroneb, chlorothalonil, cyflufenamid, cymoxanil, dichlone, diclomezine, dicloran, diethofencarb, dimethomorph, SYP-LI90 (proposed name: flumorph), dithianon, ethaboxam, etridiazole, famoxadone, fenamidone, fenoxanil, fentin, ferimzone, fluazinam, flusulfamide, fenhexamid, fosetyl-aluminium, hymexazol, iprovahcarb, IKF-916 (cyazofamid).

kasugamycin, methasulfocarb, metrafenone, nicobifen, pencycuron, phthalide, polyoxins, probenazole, propamocarb, pyroquilon, quinoxyfen, quintozene, sulfur, triazoxide, tricyclazole, triforine, validamycin, zoxamide (RH7281).
A preferred method of applying a compound of formula (I), or an agrochemical composition which contains at least one of said compounds, is foliar application. The frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen. However, the compounds of formula I can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying the compounds in soHd form to the soil, e.g. in granular form (soil application), hi crops of water rice such granulates can be applied to the flooded rice field. The compounds of formula I may also be appHed to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.
A formulation [that is, a composition containing the compound of formula (I)] and, if desired, a solid or liquid adjuvant, is prepared in a known manner, typically by intimately mixing and/or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface active compounds (surfactants).
The agrochemical formulations will usually contain from 0.1 to 99% by weight, preferably from 0.1 to 95% by weight, of the compound of formula I, 99.9 to 1% by weight, preferably 99.8 to 5% by weight, of a solid or liquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25% by weight, of a surfactant.
Advantageous rates of application are normally from 5g to 2kg of active ingredient (a.i.) per hectare (ha), preferably from lOg to 1kg a.i./ha, most preferably from 20g to 600g a.i./ha. When used as seed drenching agent, convenient dosages are from 10mg to 1g of active substance per kg of seeds.
Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations.
The following non-limiting Examples illustrate the above-described invention in more detail.
EXAMPLE 1
This Example illustrates the preparation of Compound No. 1.01.

2-Amino-4'-ethinyl-biphenyl (0.30g) and l-methyl-3-trifluoromethyl-4-chlorocarbonyl-pyrazol (0.33g) were combined in THF under cooling with ice and then pyridine (0.12ml) was added. After warming to ambient temperature the suspension was stirred for 3.5hours, poured into water and extracted twice with ethylacetate. Separation of the organic phase, drying with sodium sulfate and evaporation of the solvent and chromatographic purification on silica gel (solvent: hexaneiethylacetate 2:1) yielded 0.4g (70.2%) of Compound No. 1.01.
EXAMPLE 2
This Example illustrates the preparation of Compound No. 2.01.
To l-methyl-3-trifluoromethyl-4-pyrrol carboxylic acid (0.22g) dissolved in 10ml dichloromethane were added triethylamine (0.32ml) and 2-amino-4'-trimethylsilylethinyl-biphenyl (0.3g) and finally, under cooling with ice, bis(2-oxo-3-oxazolidinyl) chlorophosphinic acid (0.29g). After stirring for 18hours the solvents were removed under reduced pressure and the residue was taken up with ethylacetate. Washing with water and brine, drying with sodiumsulfate and evaporation of the solvent yielded 0.45g of a yellow oil which was chromatographed on silica gel (eluent: hexane:ethylacetate 2:1) to yield 0.13g (26%) of Compound No. 2.01.
EXAMPLE 3
This Example illustrates the preparation of Compound No. 1.72.
To NaH (46mg) in 5ml dry THF at 0-5C was added 2-N-formylamino-4'-(propin-l-yl)-biphenyl (0.3g) in 10ml dry THF. The reaction was kept at this temperature for 1hour and afterwards l-methyl-3-trifluoromethyl-4-chlorocarbonyl-pyrazol (0.372g) was added. The resultant suspension was stirred at room temperature ovemight, poured into brine and extracted with ethylacetate. The solvent was evaporated and the the residue was taken into methanol and sodiummethylate (10mg) was added. After 30minutes the mixture was neutralised with diluted HCl, extracted with ethylacetate and washed until neutral. Chromatographic purification on silica gel (eluent: ethylacetate:hexane 1:2) and recrystallisation fi-om toluene:hexane (4:1) yielded 0.169g of Compound No. 1.72.
EXAMPLE 4
This Example illustrates the preparation of 2- amino-4'-(trimethylsilyl)ethinyl-biphenyl (Compound No. 12.02) and 2-amino-4'-ethinyl-biphenyl (Compound No. 12.01) using a preparation according to Method F above.

To 2.5g 2-amino-4'-bromo-biphenyl (WO0264562) in piperidine (25ml) under nitrogen were added in sequence Cul (O.lg), bis(triphenylphosphino)palladium dichloride (0.35g) and trimethylsilylacetylene (2.8ml). The mixture was stirred for 22hours at room temperature and for a further 26hours at 60°C. After cooling the reaction mixture was diluted with water and extracted with ethylacetate. Then the organic phase was washed with water and dried over sodium sulfate. After evaporation of the solvents in vacuum the mixture was chromatographed on silica gel (hexane:ethylacetate 9:1) to yield 2- amino-4'-(trimethylsilyl)ethinyl-biphenyl (2g) (Compound No.12.02).
1.4g of this compound was dissolved in methanol (40ml) and potassium carbonate (0.9g) was added with cooling. The resultant suspension was stirred for 2hours, poured on ice-water and the precipitate formed was filtered off, washed thoroughly with water and dried to obtain 2-amino-4'-ethinyl-biphenyl (0.9g) (Compound No.12.01) as light tan crystals.
EXAMPLES This Example illustrates the preparation of 2-N-formylamino-4'-(propin-l-yl)-biphenyl (Compound No.12.16)
N-formylamino-4'bromo-biphenyl (3.5g) (J.Chem.Soc. 1957, 4), tributyltin(propinyl-l) (5g) (commercial from Aldrich), tetrakis(triphenylphosphine)palladium (0.37g) were combined in toluene (200ml) under nitrogen and heated to reflux for 16hours. The resultant dark mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water, dried over sodium sulfate and the solvents were evaporated at reduced pressure. The residue was taken into acetonitrile and washed repeatedly with hexane. After removal of the acetonitrile at reduced pressure and chromatography of the residue with silicagel (eluent:hexane ethylacetate 2:1) 2-N-formylamino-4'-(propin-l-yl)-biphenyl (Compound No. 12.16) (1.57g) was obtained as a Hght yellow powder.
EXAMPLE 6
This Example illustrates the preparation of 2-amino-4'(2,2-dichloro)ethylene-biphenyl (Compound No.12.07) and 2-amino-4'(chloroethinyl)-biphenyl (Compound No 12.04.
a) Preparation of 2-nitro-4'(2,2-dichloro)ethylene-biphenyl.
To 2-nitro-4'formyl-biphenyl (2g) (WO 95 03290) (prepared by Pd-catalysed coupling of ' 2-bromonnitrobenzene with 4-formyl-phenyl-boronic acid) in ethanol (70ml) was added hydrazine hydrate (95%) (1.32g) and the resultant mixture was then refluxed for 5hours. The

solvent was evaporated to dryness under reduced pressure, the residue was suspended in DMSO (30ml) and then ammonia (25%) (3ml) and freshly prepared CuCl (80mg) were sequentially added and finally tetrachlorometane (3.8g) was dropped in under coohng with water. The mixture was stirred at room temperature for 24hours and the resultant green suspension was poured into water, extracted with dichloromethane, washed with water and dried over sodium sulfate. Evaporation of the solvent and chromatography of the residue over silicagel (eluent:hexane:ethylacetate4:l) yielded 2-nitro-4'(2,2-dichloro)ethylene-biphenyl (0.8g),m.p. 58-59°C.
b) Preparation of 2-amino-4'(2,2-dichloro)ethylene-biphenyl.
2-Nitro-4'(2,2-dichloro)ethylene-biphenyl (0.76g) from step (a) was dissolved in 50%
ethanol (30ml) and heated to reflux. Then 2N HCl (0.3ml) in 50% ethanol (10ml) was added dropwise. The reaction mixture was held at reflux for 4hours, cooled to room temperature and filtered. The filtrate was neutralised with sodium bicarbonate, extracted twice with ethyl acetate and the organic phase was dried over sodium sulfate. Evaporation of the solvent under reduced pressure yielded 2-amino-4'(2,2-dichloro)ethylene-biphenyl (0.62g) (Compound No. 12.07).
c) 2-Amino-4'(2,2-dichloro)ethyIene-biphenyl (3g) was dissolved in 150ml dimethyl
sulfoxide in which 0.9g KOH (85%, powder) has been suspended. The mixture was stirred
over night at room temperature, diluted with excess of water and extracted twice with ethyl
acetate and the organic phase was dried over sodium sulfate. Evaporation of the solvent under
reduced pressure and chromatography of the residue over silicagel (eluent:hexane:ethylacetate
4:1) yielded 2.5 g 2-amino-4'(2,2-dichloro)ethylene-biphenyl as a tan coloured solid.
EXAMPLE 7 This Example illustrates the preparation of Compound Number 12.18. Step A: 2-Nitro-(4'-trimethYlsilvl)-biphenvl
2-Bromo-nitrobenzene (0.86g), 4-(trimethylsilyl)phenylboronic acid (Ig) and bis-(triphenylphosphine)-palladiumdichloride (0.3g) were dissolved in dimethoxyetane (35ml) and then a solution of sodium bicarbonate (1.3g) dissoved in water (5ml) was added dropwise. The mixture was heated for 3 hours (80°C bath temperature), cooled to room temperature, poured on to ethyl acetate:water:: 1:1 (300ml) and suction filtered. The organic phase was separated, dried over sodium sulfate and the solvent was removed. The resultant residue

(1.58g of a dark oil) was chromatographed on silica gel (eluent:hexane:ethyl acetate::4:l) to yield a yellow oil (1.12g). This compound was used in Step B. Step B: 2-Amino-(4'-trimethvlsilvl)-biphenvl [Compound 12.181
The compound obtainedfrom step A above (0.955g) and ammonium fomiiate (1.86g) were dissolved in methanol (30ml) and purged with nitrogen. To this solution, Pd (lOOmg; 10% on carbon) was added, in 2 portions. After stirring at room temperature for 15 hours, the reaction mixture was filtered and the solvent was evaporated.
FORMULATION EXAMPLES FOR COMPOUNDS OF FORMULA (1)
Working procedures for preparing formulations of the compounds of formula I such as Emulsifiable Concentrates, Solutions, Granules, Dusts and Wettable Powders are described in
WO97/33890.
BIOLOGICAL EXAMPLES: FUNGICIDAL ACTIONS
Example B-1: Action against Puccinia recondita / wheat (Brownrust on wheat)
1 week old wheat plants cv. Arina are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. One day after application, the wheat plants are inoculated by spraying a spore suspension (IxlO^uredospores/ml) on the test plants. After an incubation period of 2 days at 20°C and 95%r.h. the plants are kept in a greenhouse for 8days at 20°C and 60%r.h. The disease incidence is assessed lOdays after inoculation.
Infestation is prevented virtually completely (0-5% infestation) with each of compounds 1.01, 1.03, 1.08, 1.10, 1.12,1.13,1.15,1.16, 1.18, 1.19, 1.22, 1.24, 1.33, 1.56, 1.57, 1.60, 1.66, 1.67, 1.69, 1.70, 1.77,1.78,1.81, 1.106, 1.107, 1.138, 1.139, 1.151, 1.152, 1.154, 1.155, 1.182, 1.185, 1.251, 1.252,2.01,2.08,2.66,3.01,3.08,3.12,3.18,3.32,3.56,3.66,3.69, 3.250, 9.01, 9.06,9.15, 9.21, 9.41, 9.50, 9.53, 9.59, 15.25, 15.26 and 15.28.
Example B-2: Action against Podosphaera leucotricha / apple (Powdery mildew on apple)
5 week old apple seedlings cv. Mcintosh are treated with the formulated test compound (0.02%) active ingredient) in a spray chamber. One day after, the application apple plants are inoculated by shaking plants infected with apple powdery mildew above the test plants. After

an incubation period of 12 days at 22°C and 60%r.h. under a light regime of 14/lOhours (light/dark) the disease incidence is assessed.
hifestation is prevented virtually completely (0-5% infestation) with each of compounds. 1.01, 1.03, 1.08, 1.10, 1.12, 1.13, 1.15, 1.16, 1.18, 1.19, 1.24, 1.33, 1.35, 1.36, 1.56, 1.57, 1.66, 1.67, 1.70, 1.77, 1.78, 1.81, 1.106,1.107, 1.139, 1.151, 1.152, 1.154, 1.155, 1.182, 1.185, 1.251, 1. 252, 2.01, 2.08, 2.66, 3.01, 3.08, 3.12, 3.18, 3.32, 3.35, 3.56, 3.66, 3.69, 3.250, 9.01, 9.06,9.15, 9.21, 9.41, 9.50, 9.53, 9.59, 9.62,15.25, 15.26 and 15.28.
Example B-3: Action against Venturia inaequalis / apple (Scab on apple) 4 week old apple seedlings cv. Mcintosh are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. One day after application, the apple plants are inoculated by spraying a spore suspension (4xl0°Conidia/ml) on the test plants. After an incubation period of 4 days at 21°C and 95%r.h. the plants are placed for 4 days at 21°C and 60%r.h. in a greenhouse. After another 4 day incubation period at 21 °C and 95%r.h. the disease incidence is assessed.
Infestation is prevented virtually completely (0-5% infestation) with each of compounds. 1.01, 1.03, 1.08, 1.10,1.12, 1.13, 1.18, 1.19, 1.24, 1.33, 1.56, 1.57, 1.66, 1.67, 1.69, 1.70, 1.77, 1.78, 1.81, 1.106,1.107, 1.138, 1.152, 1.154, 1.155, 1.251, 1. 252,2.01, 2.08, 2.66, 3.01, 3.08, 3.12, 3.18, 3.32, 3.56, 3.66, 3.69, 9.01, 9.06,9.15, 9.21, 9.50 and 9.59.
Example B-4: Action against Ervsiphe graminis / barley (Powdery mildew on barley)
1 week old barley plants cv. Regina are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. One day after apphcation, the barley plants are inoculated by shaking powdery mildew infected plants above the test plants. After an incubation period of 6 days at 20°C / 18°C (day/night) and 60%r.h. in a greenhouse the disease incidence is assessed.
Infestation is prevented virtually completely (0-5% infestation) with each of compounds 1.01, 1.03, 1.08, 1.10, 1.12, 1.13, 1.15, 1.16, 1.18, 1.19, 1.24, 1.33, 1.35, 1.36, 1.56, 1.57, 1.66, 1.67, 1.70, 1.77, 1.78, 1.106, 1.107, 1.152, 1.155, 1.251,1.252,2.01,2.08,2.66,3.01, 3.08, 3.12, 3.18, 3.32, 3.35, 3.56, 3.66, 3.69, 3.250, 9.01, 9.06,9.15, 9.21, 9.41, 9.50 and 9.59.

Example B-5: Action against Botrvtis cinerea / grape (Botrytis on grapes)
5 week old grape seedlings cv. Gutedel are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. Two days after application, the grape plants are inoculated by spraying a spore suspension (IxlO°Conidia/ml) on the test plants. After an incubation period of 4 days at 21°C and 95%r.h. in a greenhouse the disease incidence is assessed.
hifestation is prevented virtually completely (0-5% infestation) with each of compounds 1.01, 1.03, 1.08 and 1.10.
Example B-6: Action against Botrvtis cinerea / tomato (Botrvtis on tomatoes)
4 week old tomato plants cv. Roter Gnom are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. Two days after application, the tomato plants are inoculated by spraying a spore suspension (IxlO°Conidia/ml) on the test plants. After an incubation period of 4 days at 20°C and 95%r.h. in a growth chamber the disease incidence is assessed.
Infestation is prevented virtually completely (0-5% infestation) with each of compounds 1.01, 1.03, 1.08, 1.10, 1.12,1.13,1.15, 1.16, 1.18, 1.19, 1.24, 1.33, 1.36, 1.56, 1.57, 1.66, 1.67, 1.69, 1-70, 1.77, 1.78, 1.106, 1.107,1.138, 1.139, 1.152, 1.155, 1.251, 1. 252, 2.01, 2.66, 3.01, 3.08, 3.12, 3.66, 3.69, 3.250, 9.06,9.15, 9.21, 9.41, 9.50 and 9.59.
Example B-7: Action against Septoria nodorum / wheat fSeptoria leaf spot on wheat) 1 week old wheat plants cv. Arina are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. One day after application, the wheat plants are inoculated by spraying a spore suspension (5xl0°Conidia/ml) on the test plants. After an incubation period of 1 day at 20T and 95%r.h. the plants are kept for 10 days at 20°C and 60%r.h. in a greenhouse. The disease incidence is assessed 11 days after inoculation.
Infestation is prevented virtually completely (0-5% infestation) with each of compounds 1.01, 1.03, 1.08 and 1.10.
Example B-8: Action against Helminthosporium teres / barley (Net blotch on barley)

1 week old barley plants cv. Regina are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. Two days after application, the barley plants are inoculated by spraying a spore suspension (3xl04conidia/ml) on the test plants. After an incubation period of 4 days at 20°C and 95%r.h. in a greenhouse the disease incidence is assessed.
Infestation is prevented virtually completely (0-5% infestation) with each of compounds 1.01, 1.03, 1.08, 1.10, 1.12, 1.13, 1.15, 1.16, 1.18, 1.19, 1.22, 1.24, 1.33, 1.36, 1.35, 1.56, 1.57, 1.60, 1.66, 1.67, 1.69, 1.70, 1.77, 1.78, 1.81, 1.106, 1.107, 1.138, 1.139, 1.151, 1.152, 1.154, 1.155, 1.182,1.185,1.251,1.252,2.01,2.08,2.66,3.01,3.08,3.12,3.18,3.32,3.35, 3.56, 3.66, 3.69, 9.01, 9.06,9.15, 9.21, 9.41, 9.50, 9.53, 9.59, 9.62, 15.25, 15.26 and 15.28.
Example B-9: Action against Altemaria solani / tomato (Early blight on tomatoes) 4 week old tomato plants cv. Roter Gnom are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. Two days after application, the tomato plants are inoculated by spraying a spore suspension (2xl0°Conidia/ml) on the test plants. After an incubation period of 3 days at 20*°C and 95%>r.h. in a growth chamber the disease incidence is assessed.
Infestation is prevented virtually completely (0-5% infestation) with each of compounds LOl, 1.03, 1.08, 1.10, 1.13, 1.15, 1.16, 1.19, 1.22, 1.24, 1.33, 1.35, 1.36, 1.56, 1.57, 1.67, 1.69, 1.70, 1.77, 1.78, 1.81, 1.107, 1.151, 1.152, 1.154, 1.155, 1.182,1.185, 1.251, 1. 252, 2.01, 3.01, 3.08, 3.12, 3.32, 3.35, 3.56, 3.69, 9.01, 9.06,9.15, 9.41, 9.50, 9.62 and 15.26.
Example B-10: Action against Uncinula necator / grape (Powdery mildew on grapes)
5 week old grape seedlings cv. Gutedel are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. One day after apphcation, the grape plants are inoculated by shaking plants infected with grape powdery mildew above the test plants. After an incubation period of 7 days at 26°C and 60%or.h. under a light regime of 14/lOhours (light/dark) the disease incidence is assessed.
Infestation is prevented virtually completely (0-5% infestation) with each of compounds 1.01, 1.03, 1.08, 1.10, 1.12, 1.13, 1.18, 1.19,1.24, 1.33, 1.56, 1.57, 1.60, 1.66, 1.67, 1.70, 1.77, 1.78, 1.81, 1.106, 1.107, 1.138, 1.139, 1.151, 1.152, 1.154, 1.155, 1.182, 1.185, 1.251, 1.

252, 2.01, 2.08, 2.66, 3.01, 3.08, 3.12, 3.32, 3.56, 3.66, 3.69, 3.250, 9.01, 9.06,9.15, 9.41, 9.50, 9.53 and 9.59.
Example B-11: Action against Septoria tritici / wheat (Septoria leaf spot on wheat)
2 week old wheat plants cv. Riband are treated with the formulated test compound (0.2% active ingredient) in a spray chamber. One day after application, wheat plants are inoculated by spraying a spore suspension (lOxlO°Conidia/ml) on the test plants. After an incubation period of 1 day at 23°C and 95% r.h., the plants are kept for 16 days at 23°C and 60% r.h. in a greenhouse. The disease incidence is assessed 18 days after inoculation.
Compounds 1.10, 1.03, 1.09, 1.70, 1.69,3.01, 1.67, 1.66,3.66,9.59,3.69, 1.33,2.66, 9.06, 3.08, 1.77, 1.78, 1.56, 1.57, 1.138,1.139, 1.12, 1.18, 1.106,1.107, 9.53, 3.32, 1.151, 1.152, 1.252, 1.155, 9.41, 3.56, 1.13, 3.12, 9.21, 1.250, 1.19 and 3.18. each show good activity in this test (







WE CLAIM:
A compound of formula (II):

where R2, R3 R4, R5, R6, R7 and n are as defined in claim 1 and Hal is bromo, chloro or iodo; provided that the compound is not a compound of formula (IIIa) according to
Tabic 0.


Documents:

4482-chenp-2007 amended pages of specification 09-06-2011.pdf

4482-chenp-2007 amended claims 09-06-2011.pdf

4482-chenp-2007 other patent document 09-06-2011.pdf

4482-chenp-2007 power of attorney 09-06-2011.pdf

4482-CHENP-2007 CORRESPONDENCE OTHERS 06-01-2011.pdf

4482-chenp-2007 examination report reply recieved 09-06-2011.pdf

4482-chenp-2007 form-1 09-06-2011.pdf

4482-chenp-2007 form-3 09-06-2011.pdf

4482-chenp-2007-abstract.pdf

4482-chenp-2007-claims.pdf

4482-chenp-2007-correspondnece-others.pdf

4482-chenp-2007-description(complete).pdf

4482-chenp-2007-form 1.pdf

4482-chenp-2007-form 26.pdf

4482-chenp-2007-form 3.pdf

4482-chenp-2007-form 5.pdf

4482-chenp-2007-pct.pdf

abs-4482-chenp-2007.jpg


Patent Number 248972
Indian Patent Application Number 4482/CHENP/2007
PG Journal Number 38/2011
Publication Date 23-Sep-2011
Grant Date 16-Sep-2011
Date of Filing 09-Oct-2007
Name of Patentee SYNGENTA PARTICIPATIONS AG
Applicant Address SCHWARZWALDALLEE 215, CH-4058 BASEL, SWITZERLAND.
Inventors:
# Inventor's Name Inventor's Address
1 LAMBERTH, CLEMENS SYNGENTA CROP PROTECTION AG, SCHWARZWALDALLE 215, CH-4058 BASEL, SWITZERLAND.
2 EHRENFREUND, JOSEF SYNGENTA CROP PROTECTION AG, SCHWARZWALDALLEE 215, CH-4058 BASEL, SWITZERLAND.
3 WALTER, HARALD SYNGENTA CROP PROTECTION AG, SCHWARZWALDALLEE 215, CH-4058 BASEL, SWITZERLAND.
PCT International Classification Number A01N 43/06
PCT International Application Number PCT/EP03/14248
PCT International Filing date 2003-12-15
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 0230155.4 2002-12-24 Germany