Herbicidal mixtures

• US 20020055435A1
• Filed: 08/24/2001
• Published: 05/09/2002
• Est. Priority Date: 08/25/2000
• Status: Active Grant

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: Intellectual Property Department
• Inventors: Baltruschat, Helmut Siegfried, Brandt, Astrid
• Granted Patent: US 6,683,027 B2
• Time in Patent Office: Days
• US Class Current: 504/103
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 25/32 Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
• CPC Class Codes: A01N 33/18 Nitro compounds
• CPC Class Codes: A01N 37/34 Nitriles
• CPC Class Codes: A01N 37/46 N-acyl derivatives
• CPC Class Codes: A01N 39/04 Aryloxy-acetic acids; Derivatives thereof
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: A01N 43/653 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• CPC Class Codes: A01N 43/76 1,3-Oxazoles; Hydrogenated 1,3-oxazoles
• CPC Class Codes: A01N 43/82 five-membered rings with three ring hetero atoms
• CPC Class Codes: A01N 43/90 having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• CPC Class Codes: A01N 47/30 Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
• CPC Class Codes: A01N 47/36 containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Abstract

The invention relates to a herbicidal composition comprising a herbicidally acceptable carrier and/or surface active agent and, as active ingredient, a synergistically effective amount of

(1) at least one compound of formula I

 in which R¹, R², A, m and n are as defined in claim 1; and

(2) at least one additional herbicidal compound, which is active against broad-leaved weeds and/or annual grasses; which provides a synergistic effect against a broad spectrum of weed species, e.g., in cereal crops. The invention also provides a method for controlling weeds by applying a synergistically effective amount of a compound (1) and a compound (2) to a locus.

Claims

1. A herbicidal composition comprising a herbicidally acceptable carrier and/or surface active agent and, as active ingredient, a synergistically effective amount of

(1) at least one 2-phenyl-4-(hetero-)aryloxypyrimidine of formula I

 

wherein

A represents an optionally substituted phenyl group or an optionally substituted 5- or 6-membered nitrogen-containing heteroaromatic group or a difluorobenzodioxolyl group;

m represents an integer from 0 to 2;

n represents an integer from 0 to 5;

R¹ (or each R¹) independently represents a halogen atom, an optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkoxyalkyl, dialkoxyalkyl, alkoxyalkoxy, alkylthio, amino, alkylamino, dialkylamino, alkoxyamino or formamidino group;

R² (or each R²) independently represents a halogen atom, an optionally substituted alkyl, alkenyl, alkinyl, haloalkyl, haloalkoxy, alkoxy, alkoxyalkyl, alkoxyalkoxy, alkylthio, haloalkylthio group or a nitro, cyano, SF₅ or a alkylsulphonyl or alkylsulfinyl group;

or ist environmentally compatible salts; and

(2) at least one additional herbicidal compound, which is active against broad-leaved weeds and/or annual grasses;

 

and/or

(3) at least one additional safening compound.

2. A herbicidal composition according to claim 1 comprising a 2-phenyl-4-(hetero-)aryloxypyrimidine of formula I, wherein

A represents a phenyl group being substituted by one chlorine or fluorine atom, or one methyl, trifluoromethyl, trifluoromethoxy or difluoromethoxy group;

m is 0; and

n is 1 or 2.

3. A herbicidal composition according to claim 2 wherein the 2-phenyl-4-(hetero-)aryloxypyrimidine of formula I is 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)-pyrimidine.

4. A herbicidal composition according to claims 1 to 3, wherein said additional herbicidal compound (2) is selected from

a) lipid biosynthesis inhibitors;

b) acetolactate synthase inhibitors (ALS);

c) photosynthesis inhibitors;

d) protoporphyrinogen-IX-oxidase inhibitors;

e) bleacher herbicides;

f) enolpyruvylshikimate 3-phosphate synthase inhibitors (EPSP);

g) glutamine synthetase inhibitors;

h) dihydropteroate synthase inhibitors (DHP);

i) mitosis inhibitors;

j) cell division inhibitors;

k) cellulose biosynthesis inhibitors;

l) uncoupling herbicides;

m) auxin herbicides;

n) auxin transport inhibitors;

or

o) various other herbicides;

5. A herbicidal composition according to claims 1 to 4, wherein said additional herbicidal compound (2) is selected from

a) a lipid biosnthesis inhibitor:

chlorazifop, clodinafop, clofop, cyhalofop, diclofop, fenoxaprop, fenoxaprop-P, fenthiaprop, fluazifop, fluazifop-P, haloxyfop, haloxyfop-P, isoxapyrifop, propaquizafop, quizalofop, quizalofop-P, trifop, alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim, butylate, cycloate, di-allate, dimepiperate, EPTC, esprocarb, ethiolate, isopolinate, methiobencarb, molinate, orbencarb, pebulate, prosulfocarb, sulfallate, thiobencarb, tiocarbazil, tri-allate, vemolate, bensulide, benfuserate or ethofumesate;

b) an acetolactate synthase inhibitor;

a sulfonyl urea type herbicide;

amidosulfuron, azimsulfuron, bensulfuron, chlorimuron, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethoxysulfuron, flazasulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, mesosulfuron, metsulfuron, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, propoxycarbazon or flucarbazon;

a sulfonamide type herbicide;

chloransulam, diclosulam, florasulam, flumetsulain, metosulam or penoxsulam;

an imidazolinone type herbicide;

imazamethabenz, imazamox, imazapic, imazapyr, imazaquin or imazethapyr;

a pyrimidyl ether;

bispyribac, pyribenzoxim, pyriftalid, pyrithiobac or pyriminobac;

c) a photosynthesis inhibitor;

a photosynthetic electron transport inhibitor;

a triazine type herbicide;

ametryn, atraton, atrazine, aziprotryne, chlorazine,cyanatryn, cyanazine, cyprazine, desmetryne, dimethamethryn, dipropetryn, egliazine, ipazine, mesoprazine, methometon, methoprotryn, procyazine, proglinazine, prometon, prometryn, propazine, sebuthylazine, secbumeton, simazine, simeton, simetryn, terbumeton, terbutylazine, terbutryn or trietazine;

or

a urea type herbicide;

anisuron, benzthiazuron, buthiuron, buturon, chlorbromuron, chloreturon, chlorotoluron, chloroxuron, difenoxuron, dimefuron, diuron, ethidimuron, fenuron, fluometuron, fluothiuron, isoproturon, isouron, linuron, methabenzthiazuron, methiuron, metobenzuron, metobromuron, metoxuron, monoisouron, monolinuron, monuron, neburon, parafluron, phenobenzuron, siduron, tebuthiuron, tetrafluron, thiadiazuron or thiazafluron;

another photosynthesis inhibitor;

a nitrile type herbicide;

bromobonil, bromoxynil, chloroxynil, iodobonil or ioxynil;

a triazinone type herbicide;

ametridione, amibuzin, hexazinone, isomethiozin, metamitron or metribuzin;

a uracil type herbicide;

bromacil, isocil, lenacil or terbacil;

a pyridazinone type herbicide;

brompyrazon, chloridazon or dimidazon;

a phenyl carbamate type herbicide;

desmedipham, phenisopham or phenmedipham;

an amide type herbicide;

propanil;

a benzothiadiazole type herbicide;

bentazone;

a phenyl pyridazine type hericide;

pyridate or pyridafol;

such as a bipyridylium type herbicide;

cyperquat, diethamquat, difenzoquat, diquat, morfainquat or paraquat;

amicarbazone, bromofenoxim, flumezin, methazole or pentanochlor;

d) a protoporphyrinogen IX oxidase inhibitor;

a diphenyl ether type herbicide;

acifluorfen, bifenox, chlomethoxyfen, chlornitrofen, ethoxyfen, fluorodifen, fluoroglycofen, fluoronitrofen, fomesafen, furyloxyfen, halosafen, lactofen, nitrofen, nitrofluorfen or oxyfluorfen;

a N-phenylphthalimide type herbicide;

cinidon-ethyl, flumiclorac, flumioxazin or flumipropyn;

a thiadiazole type herbicide;

fluthiacet or thidiazimin;

an oxadiazole type herbicide;

oxadiazon or oxadiargyl;

azafenidin, carfentrazone, sulfentrazone, pentoxazone, benzfendizone, butafenacil, pyraclonil, profluazol, flufenpyr, flupropacil, nipyraclofen, etnipromid, fluazolate (JV

     485) or pyraflufen;

e) a bleacher herbicide;

metflurazon, norflurazon, diflufenican, flufenican, picolinafen, beflubutamid, fluridone, flurochloridone, flurtamone, isoxachlortole, isoxaflutole, mesotrione, sulcotrione, benzofenap, pyrazolynate, pyrazoxyfen, benzobicyclon, amitrol, clomazone, aclonifen, ketospiradox or a 3-heterocyclyl substituted benzoyl derivative of formula II

 

in which the variables have the following meanings;

R^a, R^c are hydrogen, halogen, C_1-6-alkyl, C_1-6-haloalkyl, C_1-6-alkoxy, C_1-6-haloalkoxy, C_1-6-alkylthio, C_1-6-alkylsulfinyl or C_1-6-alkylsulfonyl;

R^b is a heterocyclic radical selected from the group;

thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl and 4,5-dihydroisoxazol-5-yl, it being possible for the nine radicals mentioned to be unsubstituted or mono- or polysubstituted by halogen, C_1-4-alkyl, C_1-4-alkoxy, C_1-4-haloalkyl, C_1-4haloalkoxy or C_1-4-alkylthio;

R^d is hydrogen, halogen or C_1-6-alkyl;

R^e is C_1-6-alkyl;

R^f is hydrogen or C_1-6-alkyl;

f) an enolpyruvylshikimate 3-phosphate synthase inhibitor (EPSP);

glyphosate;

g) a glutamine synthetase inhibitor;

bilanaphos or glufosinate;

h) a dihydropteroate synthase inhibitor (DHP);

asulam;

i) a mitosis inhibitor;

a dinitroaniline type herbicide;

benfluralin, butralin, dinitramin, ethalfluralin, fluchloralin, isopropalin, methapropalin, nitralin, oryzalin, pendimethalin, prodiamine, profluralin or trifluralin;

a phosphoramidate type herbicide;

amiprofos-methyl or butamifos;

a pyridazine type herbicide;

dithiopyr or thiazopyr;

propyzamid, tebutam, chlorthal, carbetamide, chlorbufam, chlorpropham or propham;

j) a cell division inhibitor;

a chloroacetamide type herbicide;

acetochlor, alachlor, allidochlor, butachlor, butenachlor, CDEA, delachlor, diethatyl, dimethachlor, dimethenamid, dimethenarnid-P, epronaz, metazachlor, metolachlor, S-metolachlor, pethoxamid, pretilachlor, propachlor, propisochlor, prynachlor, terbuchlor, thenylchlor or xylachlor;

an acetamide type herbicide;

diphenamid, napropamide or naproanilide;

an oxacetamide type herbicide;

flufenacet or mefenacet;

fentrazamide, anilophos, piperophos, cafenstrole, indanofan or tridiphane;

k) a cellulose biosynthesis inhibitor;

dichlobenil, chlorthiamid, isoxaben or flupoxam;

l) an uncoupling herbicide;

dinofenate, dinoprop, dinosam, dinoseb, dinoterb, DNOC, etinofen or medinoterb;

m) an auxin herbicide;

clomeprop, 2,4-D, 2,4-DB, dichlorprop, dichlorprop-P, MCPA, MCPA thioethyl, MCPB, mecoprop, mecoprop-P, 2,4,5-T, chloramben, dicamba, 2,3,6-TBA, tricamba, quinchlorac, quinmerac, clopyralid, fluroxypyr, picloram, trichlopyr or benazolin;

n) an auxin transport inhibitor;

naptalame or diflufenzopyr;

o) various other herbicide;

a flurene carboxylic acid;

chlorflurenol or flurenol;

benzoylprop, flamprop, flamprop-M, bromobutide, cimnethylin, cumyluron, daimuron, methyldymron, etobenzanid, fosamin, metam, pyributicarb, oxaziclomefone, dazomet, triaziflam or methylbromid;

or their environmentally compatible salts, esters, thioesters and amides.

6. A herbicidal composition according to claims 1 to 5, wherein said additional herbicidal compound (2) is selected from

a) a lipid biosynthesis inhibitor;

b) an acetolactate synthase inhibitor;

c) a photosynthesis inhibitors;

d) a protoporphyrinogen IX oxidase inhibitor;

i) a mitosis inhibitor;

j) a cell division inhibitor;

m) an auxine herbicide;

o) a flurene carboxylic acid herbicide.

7. A herbicidal composition according to claim 6, wherein said additional herbicidal compound (2) is selected from

b) a sulfonyl urea type herbicide or a sulfonamide type herbicide;

c) an urea-type herbicide, a triazine type herbicide, a nitrile type herbicide or a phenyl pyrazine type herbicide;

i) a dinitroaniline type herbicide,

j) an oxyacetamide herbicide herbicide.

8. A herbicidal composition according to claim 6, wherein said additional herbicidal compound (2) is selected from

a) fenoxaprop, and clodinafop

b) amidosulfuron, flupyrsulfuron, sulfosulfuron, florasulam and metosulam;

c) atrazine, cyanazine, simazine, chlorotoluron, isoproturon, linuron, neburon, bromoxynil, ioxynil and pyridate;

d) cinidon-ethyl, carfentrazone and JV 485;

i) pendimethalin;

j) flufenacet;

m) dichlorprop, MCPA, mecoprop and fluroxypyr;

o) flurenol;

9. A herbicidal composition according to claims 1 to 8, wherein said safening compound (3) is selected from benoxacor, cloquintocet, cyometrinil, dichlormid, dicyclon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxdifen, mefenpyr, mephenate, naphthalic anhydride, oxabenil and R 29148.

10. A herbicidal composition according to claim 9, wherein said safening compound (3) is selected from benoxacor, cloquintocet, dichlormid, fenchlorazole, fenclorim, fluxofenim, furilazole, isoxdifen, mefenpyr and oxabenil.

11. A herbicidal composition according to claims 1 to 8 wherein the active ingredients are selected from said 2-phenyl-4-(hetero-)aryloxypyrimidines of formula I (1) and said herbicidal compounds (2).

12. A herbicidal composition according to claims 1 or 9 to 10 wherein the active ingredients are selected from said 2-phenyl-4-(hetero-)aryloxypyrimidines of formula I (1) and said safening compounds (3).

13. A herbicidal composition according to claims 1 to 10, wherein the active ingredients are selected from said 2-phenyl-4-(hetero-)aryloxypyrimidines of formula I (1), said herbicidal compounds (2) and said safening compounds (3).

14. A herbicidal composition according to claims 1 to 11 or 13, wherein the ratio (by weight) of the 2-phenyl-4-(hetero-)aryloxypyrimidine of formula I to the additional herbicidal compound (2) is from 1:

0.002 to 1;

800.

15. A herbicidal composition as claimed in claim 14, wherein the ratio (by weight) of the 2-phenyl-4-(hetero-)aryloxypyrimidine of formula I to the additional herbicidal compound (2) is from 1:

0.05 to 1;

500.

16. A herbicidal composition as claimed in claim 15, wherein the ratio (by weight) of the 2-phenyl-4-(hetero-)aryloxypyrimidine of formula I to the additional herbicidal compound (2) is from 1:

1 to 1;

100.

17. A herbicidal composition as claimed in claims 1 to 10 or 12 to 13, wherein the ratio (by weight) of the 2-phenyl-4-(hetero-)aryloxypyrimidine of formula I to the additional safening compound (3) is from 1:

0.002 to 1;

800.

18. A herbicidal mixture comprising a herbicidally effective amount of a herbicidal composition as claimed in claims 1 to 17 and one or more carriers.

19. A method of controlling the growth of weeds at a locus which comprises applying to the locus a herbicidal composition as claimed in claims 1 to 17 or a herbicidal mixture as claimed in claim 18 before, during and/or after the emergence of undesired plants, it being possible for the active components to be applied simultaneously or in succession.

20. A method according to claim 18, wherein said compounds are applied together in a single formulation.

21. A method according to claim 18, wherein said compounds are applied in separate formulations.

22. A method for controlling the growth of weeds in cereal crops which comprises applying thereto an effective amount of a composition according to claims 1 to 17.

23. A method of combating Alopecurus myosuroides, Apera spica-venti, Lolium perenne, Setaria viridis, Galium aparine, Lamium purpureum, Matricaria inodora, Papaver rhoeas, Stellaria media and/or Veronica persica at a locus which comprises applying to the locus a herbicidally effective amount of a composition described in claims 1 to 17.