Formulation component

Patent metadata

Field	Value
Publication number	US-2018242574-A1
Application number	US-201815970512-A
Country	US
Kind code	A1
Filing date	May 3, 2018
Priority date	Jan 24, 2011
Publication date	Aug 30, 2018
Grant date	—

Abstract

The present invention relates to agrochemical compositions comprising certain benzamide compounds and to the use of those benzamide compounds as adjuvants, especially in formulations, in particular in agrochemical formulations and in environmentally friendly formulations. The invention further extends to certain novel benzamide compounds and a process to prepare such novel compounds.

First claim

1 . A method of increasing the efficacy of an herbicide when applied to unwanted plants or the locus thereof, said method comprising combining a compound of formula (I)

wherein,
m is 1;
n is an integer of 0, 1, 2, or 3;
R 1 is C(O)NR 3 R 4 ;
each is independently methyl or C 6-12 alkyl;
each R 3 is selected from the group consisting of H, methyl, ethyl, propyl or butyl;
R 4 is the group -[AO] X —R 5 , -[OA] x —R 5 , or combinations thereof, wherein A is ethyl or propyl, x is an integer of 7-18;
and each R 5 is independently H, C 1-4 alkyl, or NH 2 ,
with said herbicide, such that when said combination is applied to said unwanted plants or the locus thereof the concentration of the compound of formula (I) is in the range of 0.05% to 1% w/v or v/v of the total combination, and the efficacy of the combination in controlling unwanted plant growth is greater than that observed when the herbicide is applied in the absence of the compound of formula (I).

2 . The method of claim 1 , wherein at least one R 2 is at the para position.

3 . The method of claim 1 , wherein R 3 is H and R 4 is the group

wherein ‘b’ has the value of 9 and the sum of ‘a’ and ‘c’ is 3 or 4.

4 . The method of claim 1 , wherein n is 1.

5 . The method of claim 1 , wherein n is 0.

6 . An agrochemical composition comprising
(i) a compound of formula (I)

wherein
m is 1;
n is an integer of 0, 1, 2, or 3;
R 1 is C(O)NR 3 R 4 ;
each R 2 is independently methyl or C 6-12 alkyl;
R 3 is selected from the group consisting of H, methyl, ethyl, propyl or butyl,
R 4 is the group -[AO] x —R 5 , -[OA] x —R 5 , or combinations thereof, wherein A is ethyl or propyl, and x is an integer of 7-18; and
R 5 is H, C 1-4 alkyl, or NH 2 ,
and (ii) an agrochemical active ingredient.

7 . An agrochemical composition according to claim 6 , wherein the agrochemical composition is a herbicidal composition and the agrochemical active ingredient is an herbicide.

8 . An agrochemical composition according to claim 6 , wherein the compound of formula (I) comprises from about 0.0005% to about 90% w/v of the total composition.

9 . An agrochemical composition according to claim 6 , wherein the agrochemical is selected from the group consisting of: bicyclopyrone, mesotrione, fomesafen, tralkoxydim, napropamide, propanil, pyrimethanil, dicloran, tecnazene, toclofos methyl, flamprop M, 2,4-D, MCPA, mecoprop, clodinafop-propargyl, cyhalofop-butyl, diclofop methyl, haloxyfop, quizalofop-P, indol-3-ylacetic acid, 1-naphthylacetic acid, isoxaben, tebutam, chlorthal dimethyl, benomyl, benfuresate, dicamba, dichlobenil, benazolin, triazoxide, fluazuron, teflubenzuron, phenmedipham, acetochlor, alachlor, metolachlor, pretilachlor, thenylchlor, alloxydim, butroxydim, clethodim, cyclodim, sethoxydim, tepraloxydim, pendimethalin, dinoterb, bifenox, oxyfluorfen, acifluorfen, fluoroglycofen-ethyl, bromoxynil, ioxynil, imazamethabenz-methyl, imazapyr, imazaquin, imazethapyr, imazapic, imazamox, flumioxazin, flumiclorac-pentyl, picloram, amodosulfuron, chlorsulfuron, nicosulfuron, rimsulfuron, triasulfuron, triallate, pebulate, prosulfocarb, molinate, atrazine, simazine, cyanazine, ametryn, prometryn, terbuthylazine, terbutryn, sulcotrione, isoproturon, linuron, fenuron, chlorotoluron, metoxuron, isopyrazam, mandipropamid, azoxystrobin, trifloxystrobin, kresoxim methyl, famoxadone, metominostrobin and picoxystrobin, cyprodanil, carbendazim, thiabendazole, dimethomorph, vinclozolin, iprodione, dithiocarbamate, imazalil, prochloraz, fluquinconazole, epoxiconazole, flutriafol, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, hexaconazole, paclobutrazole, propiconazole, tebuconazole, triadimefon, trtiticonazole, fenpropimorph, tridemorph, fenpropidin, mancozeb, metiram, chlorothalonil, thiram, ziram, captafol, captan, folpet, fluazinam, flutolanil, carboxin, metalaxyl, bupirimate, ethirimol, dimoxystrobin, fluoxastrobin, orysastrobin, metominostrobin, prothioconazole, thiamethoxam, imidacloprid, acetamiprid, clothianidin, dinotefuran, nitenpyram, fipronil, abamectin, emamectin, bendiocarb, carbaryl, fenoxycarb, isoprocarb, pirimicarb, propoxur, xylylcarb, asulam, chlorpropham, endosulfan, heptachlor, tebufenozide, bensultap, diethofencarb, pirimiphos methyl, aldicarb, methomyl, cyprmethrin, bioallethrin, deltamethrin, lambda cyhalothrin, cyhalothrin, cyfluthrin, fenvalerate, imiprothrin, permethrin, halfenprox, paclobutrazole, 1-methylcyclopropene, benoxacor, cloquintocet-mexyl, cyometrinil, dichlormid, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, mefenpyr-diethyl, MG-191, naphthalic anhydride, and oxabetrinil.

10 . An agrochemical composition according to claim 6 , wherein the composition is formulated as, or comprised by a microcapsule.

11 . An agrochemical composition according to claim 6 , wherein the composition is an emulsion concentrate (EC) or dispersion concentrate (DC).

12 . An agrochemical composition according to claim 6 , comprising at least one additional component selected from the group consisting of an agrochemical, an adjuvant, a surfactant, an emulsifier, and a solvent.

13 . An agrochemical composition, comprising:
(i) an agrochemically active adjuvant having formula (I)

wherein
m is 1;
n is an integer of 0, 1, 2, or 3;
R 1 is C(O)NR 3 R 4 ;
each R 2 is independently methyl or C 6-12 alkyl;
R 3 is selected from the group consisting of H, methyl, ethyl, propyl or butyl, and
R 4 is an alkoxylated chain ending with H, C 1-4 alkyl, or NH 2 ; and
and (ii) an agrochemical active ingredient.

14 . A method of making a benzoic acid derivative, comprising:
reacting a compound of formula (II)

wherein R 2 is C 1-15 alkyl, and
n is an integer of 0, 1, 2, or 3,

with NR 3 R 4 , wherein
R 3 is selected from the group consisting of H, methyl, ethyl, propyl or butyl, and
R 4 is an alkoxylated chain ending with H, C 1-4 alkyl, or NH 2 .

15 . The method of claim 14 , wherein the reacting comprises using SOCl 2 or N,N′-Dicyclohexylcarbodiimide.

Assignees

• Syngenta Ltd

Inventors

• Bell Gordon
• Perry Richard Brian
• Ramsay Julia Lynne
• Stock David
• Taylor Philip

Classifications

• A01N41/10

  Sulfones; Sulfoxides · CPC title

• A01N43/54

  1,3-Diazines; Hydrogenated 1,3-diazines · CPC title

• C07C233/65 Primary

  having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals · CPC title

• A01N25/00 Primary

  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 · CPC title

• A01N37/20

  containing the group [IMAGE cpc-sch-A01N-0935.gif], wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof · CPC title