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WO2018108612A1 - Herbicidal compositions comprising isoxazolo[5,4-b]pyridines - Google Patents

Herbicidal compositions comprising isoxazolo[5,4-b]pyridines Download PDF

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Publication number
WO2018108612A1
WO2018108612A1 PCT/EP2017/081426 EP2017081426W WO2018108612A1 WO 2018108612 A1 WO2018108612 A1 WO 2018108612A1 EP 2017081426 W EP2017081426 W EP 2017081426W WO 2018108612 A1 WO2018108612 A1 WO 2018108612A1
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compositions
component
formula
methyl
composition according
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PCT/EP2017/081426
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French (fr)
Inventor
Thomas Zierke
Markus Kordes
Ryan Louis NIELSON
Thomas Seitz
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Basf Se
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • compositions comprising isoxazolo[5,4-b]pyridines
  • the present invention relates to herbicidal compositions comprising at least one isoxazolo[5,4- b]pyridine herbicide I .A, I.B or I.C, or an N-oxide, or an agriculturally useful salt thereof, and at least one further compound selected from herbicidally active compounds of the formula 11.1 and II.2, or an N-oxide, or an agriculturally useful salt thereof, and, if desired, a safener C or at least one further herbicide D.
  • the present invention also relates to the use of such a composition for controlling unwanted vegetation and to a method for controlling unwanted vegetation, which comprises allowing a composition to act on plants, their seeds and/or their habitat.
  • crop protection compositions it is desirable to increase the specific activity of an active compound and the reliability of the effect. It is particularly desirable for the crop protection composition to control the harmful plants effectively, but at the same time to be compatible with the useful plants in question. It is also desirable to provide a broad spectrum of activity allowing the simultaneous control of a variety of harmful plants. Frequently this cannot be achieved using a single herbicidally active compound. With many highly effective herbicides, there is the problem that their compatibility with useful plants, in particular dicotyledonous crop plants, such as cotton, oilseed rape and graminaceous plants, such as barley, millet, corn, rice, wheat and sugar cane, is not always satisfactory, i.e.
  • Herbicidal isoxazolo[5,4-b]pyridines of formulae I .A, I.B and I.C and their synthesis are known from WO 2012/010633 A1. Routes for the synthesis of isoxazolo[5,4-b]pyridine compounds are known from Elbannany et al, Pharmazie (1988), 43(2), 128-129 and Volochnyuk et al, Journal of Combinatorial Chemistry (2010), 12(4), 510-517. The isoxazolo[5,4-b]pyridine of formula I .A was described in herbicidal compositions with other herbicides and/or safeners in WO
  • compositions which are highly active against unwanted harmful plants, showing enhanced activity in the sense of a synergistic effect.
  • the compositions should have good compatibility with useful plants.
  • the compositions according to the invention should have a broad spectrum of activity.
  • the present invention relates to herbicidal compositions comprising as component A) at least nsisting of
  • R 1 is methyl or methoxy
  • R 2 is hydrogen, methyl or ethoxy
  • A is a heteroaryl group, which is unsubstituted or substituted with 1 , 2 or 3 radicals selected from the group consisiting of Ci-C6-alkyl or Ci-C6-haloalkyl;
  • R 1 is chlorine, methyl or methoxy
  • R 2 is hydrogen, chlorine, methyl or ethoxy
  • A is a heteroaryl group, which is unsubstituted or substituted with 1 , 2 or 3 radicals selected from the group consisiting of Ci-C6-alkyl or Ci-C6-haloalkyl; and, if desired, as component C) safeners.
  • C n -C m indicates the number of carbon atoms possible in each case in the substituent or substituent moiety in question.
  • Ci-C6-alkyl refers to a straight-chained or branched saturated hydrocarbon group having 1 to 6 carbon atoms, for example methyl, ethyl, propyl, 1 -methylethyl, butyl,
  • Ci-C6-haloalkyl refers to a straight-chained or branched alkyl group having 1 to 6 carbon atoms (as defined above), wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example chloromethyl,
  • heteroaryl refers to 5- or 6-membered aromatic ring systems incuding besides carbon atoms, 1 , 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S; for example, a 5-membered heteroaryl such as pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-3-yl,
  • a 6-membered heteroaryl such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
  • the isoxazolo[5,4-b]pyridine compounds of formula I. A, I.B and I.C and the herbicides of the formula 11.1 and II.2 have ionizable functional groups. They can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.
  • Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, C1-C4- alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium, tetradecylammonium,
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide,
  • the invention relates in particular to compositions in the form of herbicidally active agrochemical compositions comprising a herbicidally effective amount of an active compound combination comprising at least one isoxazolo[5,4-b]pyridine compound of formula I .A, I.B or I.C, or an N- oxide, or an agriculturally useful salt thereof, and at least one further herbicide selected from a herbicide of the formula 11.1 or II.2, or an N-oxide, or an agriculturally useful salt thereof, and, if desired, safeners C or at least one further herbicide D, and at least one liquid and/or solid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for agrochemical compositions.
  • An agrochemical composition comprises a pesticidally effective amount of at least one composition according to the invention.
  • the term "effective amount” denotes an amount of the active ingredients, which is sufficient for controlling unwanted plants, especially for controlling unwanted plants in cultivated plants and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the plants to be controlled, the treated cultivated plant or material, the climatic conditions and the specific composition according to the invention used.
  • the invention furthermore relates to a method for controlling unwanted vegetation, in particular in fields where crop plants are cultivated.
  • the invention also relates to a method for the desiccation or defoliation of plants.
  • the time frame within which the desired herbicidal action can be achieved, may be expanded by the compositions according to the invention. This allows a more flexibly timed application of the compositons according to the present invention in comparison with the single compounds.
  • compositions according to the invention have better herbicidal activity, i.e. better activity against harmful plants, than would have been expected based on the herbicidal activity observed for the individual components A or B, or a broader activity spectrum.
  • the herbicidal activity to be expected for compositions based on the individual compound can be calculated using the method of S. R. Colby (1967) "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, p. 22 ff..
  • the value E which represents the expected additive activity of the individual active compounds, was calculated using the formula
  • X percent activity using active component A at an application rate a
  • E expected activity (in %) by A + B at application rates a + b.
  • compositions comprise as component A isoxazolo[5,4- b]pyridine of formula I .A or an agriculturally acceptable salt thereof.
  • the isoxazolo[5,4-b]pyridine compounds of formula I .A. I.B or I.C or the herbicides of the formula 11.1 or II.2, the safeners C or the further herbicides D as described herein, are capable of forming geometrical isomers, it is possible to use both, the pure isomers and mixtures thereof, in the compositions according to the invention.
  • compositions comprising as component B a herbicide selected from the group consisting of
  • compositions wherein component A is the compound of the formula I.A and component B is selected from the group consisting of compounds of the formulae II.A, 5S-II.A, N-C, II. D, II. F, II.G, II.H and II.J; in particular component B is 5S-II.A or II. D.
  • component A is the compound of the formula I.A and component B is selected from the group consisting of compounds of the formulae 4R,5S-II.A, 4S,5S-II.A, II. Ca, II. Cb, II.Fa and II.Fb, or component B is selected from mixtures of these stereoisomers.
  • Compound ll.Ca is herein referred to as ⁇ 4S, 5R)-5-ethoxy-4-hydroxy-1 -methyl-3-[4- (trifluoromethyl)-2-pyridyl]imidazolidin-2-one.
  • Compound ll.Cb is herein referred to as (4R, 5R)-5-ethoxy-4-hydroxy-1 -methyl-3-[4- (trifluoromethyl)-2-pyridyl]imidazolidin-2-one.
  • Compound 11. Fa is herein referred to as (4R, 5S)-1 -(5-tert-butylisoxazol-3-yl)-4-ethoxy-5- hydroxy-3-methyl-imidazolidin-2-one.
  • Compound II.Fb is herein referred to as (4R, 5R)-1 -(5-tert-butylisoxazol-3-yl)-4-ethoxy-5- hydroxy-3-methyl-imidazolidin-2-one.
  • Compound 4R,5S-II.A is herein referred to as (4R,5SJ-4-hydroxy-1 -methoxy-5-methyl-3-[4- trifluoromethyl)-2-pyridyl]imidazolidin-2-one.
  • 4S,5S-II.A is herein referred to as (4S,5SJ-4-hydroxy-1 -methoxy-5-methyl-3-[4- (trifluoromethyl)-2-pyridyl]imidazolidin-2-one.
  • component A is the compound of the formula I.A and component B is selected from the stereoisomers of the compound of the formula II.C, ⁇ 4R, 5R)-5-ethoxy-4-hydroxy-1 - methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one and (4S, 5R)-5-ethoxy-4-hydroxy-1 - methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, or mixtures of these stereoisomers.
  • component A is the compound of the formula I.A and component B is selected from the stereoisomers of the compound of the formula II.
  • F (4R, 5R)-1 -(5-tert- butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one and (4R, 5S)-1 -(5-tert- butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one, or mixtures of these stereoisomers.
  • component A is the compound of the formula I.A and component B is selected from the stereoisomers of the compound of the formula 11.
  • A (4R,5S,)-4-hydroxy-1 - methoxy-5-methyl-3-[4-trifluoromethyl)-2-pyridyl]imidazolidin-2-one and (4S,5S J-4-hydroxy-l - methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, or mixtures of these stereoisomers.
  • ternary compositions which correspond to the binary compositions mentioned above and additionally comprise a safener C.
  • Particularly preferred safeners C namely C.1 to C.17, are listed below in table C.
  • Safeners C are known from, for example, The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Science Society of America, 1998.
  • compositions according to the invention may comprise further herbicides D selected from the group consisiting of pinoxaden, clethodim, clodinafop-propargyl, chlorsulfuron, florasulam, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, mesosulfuron-methyl, metazosulfuron, metsulfuron-methyl, nicosulfuron, penoxsulam, pyroxsulam,thiencarbazone-methyl,
  • compositions may comprise further herbicides D selected from the group consisting of atrazine, terbutylazine, mesotrione, bicyclopyron, S-metolachlor,
  • topramezone dicamba, bentazone, DMTA-p, pyroxasulfone, pendimethylin, atrazine, mesotrione and bicyclopyrone.
  • herbicides D and safeners C having a carboxyl group can be employed in the form of the acid or in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative in the compositions according to the invention.
  • suitable salts include those, where the counterion is an agriculturally acceptable cation.
  • suitable salts of dicamba are dicamba-sodium, dicamba- potassium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba- isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicamba- trolamine, dicamba-N,N-bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine.
  • a suitable ester are dicamba-methyl and dicamba-butotyl.
  • Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D- diethylammonium, 2,4-D-diethanolammonium (2,4-D-diolamine), 2,4-D-triethanolammonium, 2,4-D-isopropylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D- dodecylammonium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2- hydroxypropyl)ammonium, 2,4-D-tris(isopropyl)ammonium, 2,4-D-trolamine, 2,4-D-lithium, 2,4- D-sodium.
  • esters of 2,4-D are 2,4-D-butotyl, 2,4-D-2-butoxypropyl, 2,4-D- 3-butoxypropyl, 2,4-D-butyl, 2,4-D-ethyl, 2,4-D-ethylhexyl, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D- isopropyl, 2,4-D-meptyl, 2,4-D-methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl and clacyfos.
  • Suitable salts of 2,4-DB are for example 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB- dimethylammonium.
  • Suitable esters of 2,4-DB are for example 2,4-DB-butyl and 2,4-DB-isoctyl.
  • Suitable salts of dichlorprop are for example dichlorprop-sodium, dichlorprop-potassium and dichlorprop-dimethylammonium. Examples of suitable esters of dichlorprop are dichlorprop- butotyl and dichlorprop-isoctyl.
  • Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl, MCPA-dimethyl- ammonium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA- isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA- olamine, MCPA-potassium, MCPA-sodium and MCPA-trolamine.
  • a suitable salt of MCPB is MCPB sodium.
  • a suitable ester of MCPB is MCPB-ethyl.
  • Suitable salts of clopyralid are clopyralid-potassium, clopyralid-olamine and clopyralid-tris-(2- hydroxypropyl)ammonium.
  • Example of suitable esters of clopyralid is clopyralid-methyl.
  • Examples of a suitable ester of fluroxypyr are fluroxypyr-meptyl and fluroxypyr-2-butoxy-1 - methylethyl, wherein fluroxypyr-meptyl is preferred.
  • Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram- triisopropanolammonium, picloram-triisopropylammonium and picloram-trolamine.
  • a suitable ester of picloram is picloram-isoctyl.
  • a suitable salt of triclopyr is triclopyr-triethylammonium.
  • Suitable esters of triclopyr are for example triclopyr-ethyl and triclopyr-butotyl.
  • Suitable salts and esters of chloramben include chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium and chloramben-sodium.
  • Suitable salts and esters of 2,3,6-TBA include 2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA- potassium and 2,3,6-TBA-sodium.
  • Suitable salts and esters of aminopyralid include aminopyralid-potassium, aminopyralid- dimethylammonium, and aminopyralid-tris(2-hydroxypropyl)ammonium.
  • Suitable salts of glyphosate are for example glyphosate-ammonium, glyphosate-diammonium, glyphoste-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-trimesium as well as the ethanolamine and diethanolamine salts, preferably glyphosate-diammonium, glyphosate-isopropylammonium and glyphosate- trimesium (sulfosate).
  • a suitable salt of glufosinate is for example glufosinate-ammonium.
  • a suitable salt of glufosinate-P is for example glufosinate-P-ammonium.
  • Suitable salts and esters of bromoxynil are for example bromoxynil-butyrate, bromoxynil- heptanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.
  • Suitable salts and esters of ioxonil are for example ioxonil-octanoate, ioxonil-potassium and ioxonil-sodium.
  • Suitable salts and esters of mecoprop include mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop- methyl, mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.
  • Suitable salts of mecoprop-P are for example mecoprop-P-butotyl, mecoprop-P- dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P-sodium.
  • a suitable salt of diflufenzopyr is for example diflufenzopyr-sodium.
  • a suitable salt of naptalam is for example naptalam-sodium.
  • Suitable salts and esters of aminocyclopyrachlor are for example aminocyclopyrachlor- dimethylammonium, aminocyclopyrachlor-methyl, aminocyclopyrachlor- triisopropanolammonium, aminocyclopyrachlor-sodium and aminocyclopyrachlor-potassium.
  • a suitable salt of quinclorac is for example quinclorac-dimethylammonium.
  • a suitable salt of quinmerac is for example quinmerac-dimethylammonium.
  • a suitable salt of imazamox is for example imazamox-ammonium.
  • Suitable salts of imazapic are for example imazapic-ammonium and imazapic- isopropylammonium.
  • Suitable salts of imazapyr are for example imazapyr-ammonium and imazapyr- isopropylammonium.
  • a suitable salt of imazaquin is for example imazaquin-ammonium.
  • Suitable salts of imazethapyr are for example imazethapyr-ammonium and imazethapyr- isopropylammonium.
  • a suitable salt of topramezone is for example topramezone-sodium.
  • binary compositions refers to compositions comprising one or more isoxazolo[5,4- b]pyridines of the formula I .A, I.B or I.C (component A), and one or more herbicides of the formula 11.1 or II.2 or subformulae thereof as defined herein (component B).
  • ternary compositions refers to compositions comprising one or more isoxazolo[5,4- b]pyridines of the formula I.A, I.B or I.C (component A), and one or more, herbicides of the formula 11.1 or II.2 or subformulae thereof as defined herein (component B), and a third component, which may be a further herbicide D as defined herein or one or more safeners C as defined herein.
  • the weight ratio of the active components A:B is generally in the range of from 1 :500 to 500:1 , or in the range of from 1 :250 to 250:1 , or in the range of from 1 :125 to 125:1 , or in the range of from 1 :50 to 50: 1 , or in the range of from 1 :20 to 20: 1 , or in the range of from 1 :5 to 5:1 .
  • the weight ratio of the active components I.A:B is in the range of from 1 :10 to 10:1 or more preferably from 1 :5 to 5:1 , in a specially preferred embodiment 1 :3 to 3:1 , for example 1 :1 , 1 .5:1 , 2:1 , 1 :1.5 or 1 :2.
  • the relative proportions by weight of the components A:B are generally in the range of from 1 :500 to 500:1 , or in the range of from 1 :250 to 250:1 , or in the range of from 1 :125 to 125:1 , or the range of from 1 :50 to 50:1 , or in the range of from 1 :20 to 20:1 , or in the range of from 1 :5 to 5:1 ; and wherein the weight ratio of the components A:C or A:D is generally in the range of from 1 :500 to 500:1 , or in the range of from 1 :250 to 250:1 , or in the range of from 1 :125 to 125:1 , or the range of from 1 :50 to 50:1 , or in the range of from 1 :20 to 20:1 , or in the range of from 1 :5 to 5:1 ; and the weight ratio of the components B:C is generally in the range of from 1 :500 to 500:1 ,
  • compositions mentioned below in table 1 wherein each
  • composition comprises isoxazolo[5,4-b]pyridine of formula I.A, a component B and, if desired, the safener C as defined for each individual composition in one row of table 1 below
  • compositions no. M1.1 to M1.270 are compositions no. M1.1 to M1.270.
  • compositions M2.1 to M2.270 which differ from the corresponding
  • compositions M1.1 to M1.270 in table 1 only in that they comprise as the active component A, instead of the isoxazolo[5,4-b]pyridine of formula I.A, the isoxazolo[5,4-b]pyridine of formula I.B. Also preferred are compositions M3.1 to M3.270, which differ from the corresponding
  • compositions M1.1 to M1.270 in table 1 only in that they comprise as the active component A, instead of the isoxazolo[5,4-b]pyridine of formula I.A, the isoxazolo[5,4-b]pyridine of formula I.C.
  • the specific number for each single composition is deductible as follows: for example, composition M1.18 comprises the compound of the formula I.A, the compound of the formula 4S,5S-II.A and the safener C.1 (benoxacor, as defined in table C).
  • M1.12 I.A+II.H; M1.13: I.A+II.J; M1.14: I.A+II.K; M1.15: I.A+II.L; M1.16: I.A+II.A+C.1; M1.17: I.A+4R,5S-II.A+C1; M1.18: I.A+4S,5S-II.A+C1; M1.19: I.A+II.B+C.1; M1.20: I.A+II.Ca+C.1; M1.21: I.A+II.Cb+C.1; M1.22: I.A+II.D+C.1; M1.23: I.A+II.E+C.1; M1.24: I.A+II.Fa+C.1; M1.25: I.A+II.Fb+C.1; M1.26: I.A+II.G+C.1; M1.2
  • M1.159 I.A+II.Fa+C.10
  • M1.160 I.A+II.Fb+C.10
  • M1.161 I.A+II.G+C.10
  • M1.162 I.A+II.G+C.10
  • M1.173 I.A+II.E+C.11 ; M1.174: I.A+II.Fa+C.11 ; M1.175: I.A+II.Fb+C.11 ; M1.176:
  • M1.191 I.A+II.G+C.12; M1.192: I.A+II.H+C.12; M1.193: I.A+II.J+C.12; M1.194: I.A+II.K+C.12; M1.195: I.A+II.L+C.12; M1.196: I.A+II.A+C.13; M1.197: I.A+4R,5S-II.A+C13; M1.198:
  • M1.220 I.A+II.Fb+C.14; M1.221: I.A+II.G+C.14; M1.222: I.A+II.H+C.14; M1.223: I.A+II.J+C.14; M1.224: I.A+II.K+C.14; M1.225: I.A+II.L+C.14; M1.226: I.A+II.A+C.15; M1.227: I.A+4R,5S- II.A+C.15; M1.228: I.A+4S,5S-II.A+C15; M1.229: I.A+II.B+C.15; M1.230: I.A+II.Ca+C.15; M1.231: I.A+II.Cb+C.15; M1.232: I.A+II.D+C.15; M1.233: I.A+II.E+C.15; M1.234:
  • M1.238 I.A+II.J+C.15; M1.239: I.A+II.K+C.15; M1.240: I.A+II.L+C.15; M1.241: I.A+II.A+C.16; M1.242: I.A+4R,5S-II.A+C16; M1.243: I.A+4S,5S-II.A+C16; M1.244: I.A+II.B+C.16; M1.245: I.A+II.Ca+C.16; M1.246: I.A+II.Cb+C.16; M1.247: I.A+II.D+C.16; M1.248: I.A+II.E+C.16;
  • M1.249 I .A+l I .Fa+C.16; M1.250: I.A+II.Fb+C.16; M1.251: I.A+II.G+C.16; M1.252:
  • M1 .263 I.A+II.E+C.17
  • M1.264 I.A+II.Fa+C.17
  • M1.265 I.A+II.Fb+C.17
  • M1.266
  • compositions M4.1 to M4.270 which differ from the corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise pinoxaden as further herbicide D.
  • compositions M5.1 to M5.270 which differ from the corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise clethodim as further herbicide D.
  • compositions M6.1 to M6.270 which differ from the corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise clodinafop-propargyl as further herbicide D.
  • compositions M7.1 to M7.270 which differ from the corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise chlorsulfuron as further herbicide D.
  • compositions M8.1 to M8.270 which differ from the corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise florasulam as further herbicide D.
  • compositions M9.1 to M9.270 which differ from the corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise imazamox as further herbicide D.
  • compositions M10.1 to M10.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise imazapic as further herbicide D.
  • compositions M1 1.1 to M1 1 .270 which differ from the
  • compositions M1.1 to M1 .270 only in that they additionally comprise imazapyr as further herbicide D.
  • compositions M12.1 to M12.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise imazaquin as further herbicide D.
  • compositions M13.1 to M13.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise imazethapyr as further herbicide D.
  • compositions M14.1 to M14.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise
  • compositions M15.1 to M15.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise
  • metazosulfuron as further herbicide D.
  • compositions M16.1 to M16.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise metsulfuron- methyl as further herbicide D.
  • compositions M17.1 to M17.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise nicosulfuron as further herbicide D.
  • compositions M18.1 to M18.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise penoxsulam as further herbicide D.
  • compositions M19.1 to M19.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise pyroxsulam as further herbicide D.
  • compositions M20.1 to M20.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise
  • compositions M21.1 to M21 .270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise
  • compositions M22.1 to M22.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise tribenuron- methyl as further herbicide D.
  • compositions M23.1 to M23.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise atrazine as further herbicide D.
  • compositions M5.1 to M5.270 which differ from the corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise bentazon as further herbicide D.
  • compositions M24.1 to M24.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise bromoxynil as further herbicide D.
  • compositions M25.1 to M25.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise metribuzin as further herbicide D.
  • compositions M26.1 to M26.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise paraquat- dichloride as further herbicide D.
  • compositions M27.1 to M27.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise acifluorfen as further herbicide D.
  • compositions M28.1 to M28.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise
  • compositions M29.1 to M29.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise flumioxazin as further herbicide D.
  • compositions M30.1 to M30.270 which differ from the corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise fomesafen as further herbicide D.
  • compositions M31.1 to M31 .270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise oxadiargyl as further herbicide D.
  • compositions M32.1 to M32.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise oxyfluorfen as further herbicide D.
  • compositions M33.1 to M33.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise saflufenacil as further herbicide D.
  • compositions M34.1 to M34.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise
  • compositions M35.1 to M35.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise isoxaflutole as further herbicide D.
  • compositions M36.1 to M36.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise mesotrione as further herbicide D.
  • compositions M37.1 to M37.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise tembotrione as further herbicide D.
  • compositions M38.1 to M38.270 which differ from the
  • compositions M1.1 to M1 .270 only in that they additionally comprise
  • topramezone as further herbicide D.
  • compositions M39.1 to M39.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise
  • compositions M40.1 to M40.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise
  • compositions M41.1 to M41 .270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise
  • compositions M42.1 to M42.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise glyphosate as further herbicide D.
  • compositions M43.1 to M43.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise glufosinate as further herbicide D.
  • compositions M44.1 to M44.270 which differ from the corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise acetochlor as further herbicide D.
  • compositions M45.1 to M45.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise
  • compositions M46.1 to M46.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise metolachlor as further herbicide D.
  • compositions M47.1 to M47.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise S- metolachlor as further herbicide D.
  • compositions M48.1 to M48.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise
  • compositions M49.1 to M49.270 which differ from the
  • compositions M1.1 to M1 .270 only in that they additionally comprise
  • compositions M50.1 to M50.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise dicamba as further herbicide D.
  • compositions M51.1 to M51 .270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise fluroxypyr as further herbicide D.
  • compositions M52.1 to M52.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise 2,4-D as further herbicide D.
  • compositions M53.1 to M53.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise MCPA as further herbicide D.
  • compositions M54.1 to M54.270 which differ from the
  • compositions M1.1 to M1 .270 only in that they additionally comprise quinclorac as further herbicide D.
  • compositions M55.1 to M55.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise
  • compositions M56.1 to M56.270 which differ from the
  • compositions M1.1 to M1 . 34 only in that they additionally comprise pyridate as further herbicide D.
  • compositions M57.1 to M57.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise halauxifen as further herbicide D.
  • compositions M58.1 to M58.270 which differ from the
  • compositions M1 .1 to M1 .270 only in that they additionally comprise trifludimoxazin as further herbicide D.
  • agrochemical compositions e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • agrochemical composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g.
  • WP WP
  • SP WS
  • DP DS
  • pressings e.g. BR, TB, DT
  • granules e.g. WG, SG, GR, FG, GG, MG
  • insecticidal articles e.g. LN
  • gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF).
  • agrochemical compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants,
  • compatibilizers for bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,
  • tetrahydronaphthalene alkylated naphthalenes
  • alcohols e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol
  • glycols DMSO
  • ketones e.g. cyclohexanone
  • esters e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone
  • fatty acids phosphonates
  • amines amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
  • Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharides e.g. cellulose, starch
  • fertilizers
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates.
  • Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • Examples of phosphates are phosphate esters.
  • Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-substituted fatty acid amides are fatty acid glucamides or fatty acid
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target.
  • examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water- soluble dyes.
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron
  • tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • Water-soluble concentrates (SL, LS) 10-60 wt% of a compostion according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) ad 100 wt%.
  • the active substance dissolves upon dilution with water.
  • composition according to the invention 5-25 wt% of a composition according to the invention and 1 -10 wt% dispersant (e. g.
  • polyvinylpyrrolidone are dissolved in organic solvent (e.g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion.
  • organic solvent e.g. cyclohexanone
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e.g. aromatic hydrocarbon
  • Emulsions (EW, EO, ES)
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e.g. aromatic hydrocarbon
  • a composition according to the invention In an agitated ball mill, 20-60 wt% of a composition according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1 -2 wt% thickener (e.g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • 0,1 -2 wt% thickener e.g. xanthan gum
  • compositions according to the invention are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • wt% of a composition according to the invention are ground in a rotor-stator mill with addition of 1 -5 wt% dispersants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g. alcohol ethoxylate) and solid carrier (e.g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • wetting agents e.g. alcohol ethoxylate
  • solid carrier e.g. silica gel
  • a composition according to the invention In an agitated ball mill, 5-25 wt% of a composition according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1 -5 wt% thickener (e.g. carboxymethylcellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • 1 -5 wt% thickener e.g. carboxymethylcellulose
  • wt% of a composition according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
  • organic solvent blend e.g. fatty acid dimethylamide and cyclohexanone
  • surfactant blend e.g. alcohol ethoxylate and arylphenol ethoxylate
  • An oil phase comprising 5-50 wt% of a composition according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g.
  • methylmethacrylate, methacrylic acid and a di- or triacrylate are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules.
  • a protective colloid e.g. polyvinyl alcohol.
  • Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g.
  • diphenylmethene-4,4'-diisocyanate are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol).
  • a protective colloid e.g. polyvinyl alcohol.
  • the addition of a polyamine results in the formation of polyurea microcapsules.
  • the monomers amount to 1 -10 wt%.
  • the wt% relate to the total CS composition.
  • Dustable powders (DP, DS)
  • compositions according to the invention are ground finely and mixed intimately with solid carrier (e.g. finely divided kaolin) ad 100 wt%.
  • solid carrier e.g. finely divided kaolin
  • a composition according to the invention is ground finely and associated with solid carrier (e.g. silicate) ad 100 wt%.
  • Granulation is achieved by extrusion, spray-drying or the fluidized bed.
  • compositions according to the invention are dissolved in organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%.
  • organic solvent e.g. aromatic hydrocarbon
  • the agrochemical composition types i) to xiii) may optionally comprise further auxiliaries, such as 0,1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1 -1 wt% anti-foaming agents, and 0,1 -1 wt% colorants.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • Solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds.
  • the compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before or during sowing.
  • compositions according to the invention onto plant propagation material especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material.
  • they are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix).
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
  • the user applies the agrochemical composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • either individual components of the agrochemical composition according to the invention or partially premixed components may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
  • individual components of the agrochemical composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
  • the isoxazolo[5,4-b]pyridines of the formulae I. A, I.B or I.C (component A) and the at least one further herbicide of the formulae 11.1 or II.2 (component B) can be formulated and applied jointly or separately, simultaneously or in succession, before, during or after the emergence of the plants. In case of separate application, the order of the application of the components A and B is of minor importance. It is important that the at least one isoxazolo[5,4-b]pyridine of the formula I.A, I.B or I.C and the at least one further herbicide of the formulae 11.1 or II.2 are present simultaneously at the site of action, i.e. are at the same time in contact with or taken up by the plant to be controlled.
  • compositions according to the invention are suitable as herbicides. They are suitable as such or as an appropriately formulated composition (agrochemical composition).
  • compositions control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leafed weeds and grass weeds in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
  • the compositions according to the invention are applied to the plants mainly by spraying the leaves.
  • the application can be carried out using, for example, water as carrier by customary spraying techniques using spray liquor amounts of from about 100 to 1000 l/ha (for example from 300 to 400 l/ha).
  • the herbicidal compositions may also be applied by the low-volume or the ultra-low-volume method, or in the form of microgranules.
  • herbicidal compositions according to the present invention can be done before, during and/or after, preferably during and/or after, the emergence of the undesirable plants.
  • the herbicidal compositions according to the present invention can be applied pre- or post-emergence. If the active components A and B, and, if appropriate, C and/or D, are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).
  • compositions of the present invention on their own or jointly in combination with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria or with groups of active compounds which regulate growth.
  • other crop protection agents for example with agents for controlling pests or phytopathogenic fungi or bacteria or with groups of active compounds which regulate growth.
  • miscibility with mineral salt solutions which are employed for treating nutritional and trace element deficiencies.
  • Non-phytotoxic oils and oil concentrates can also be added.
  • the amounts of active substances applied i.e. components A and B, and, if appropriate, safeners C and/or further herbicides D, without formulation auxiliaries, are, depending on the kind of effect desired, from 0.001 to 3 kg/ha, preferably from 0.005 to 2.5 kg/ha and in particular from 0.01 to 2 kg/ha of active substance (a.s.).
  • the application rates of the isoxazolo[5,4- b]pyridine of formula I .A, I.B or I.C are in the range from 0.1 g/ha to 5000 g/ha and preferably in the range from 1 g/ha to 2500 g/ha, from 5 g/ha to 2000 g/ha, from 10 to 750 g/ha, more preferably from 50 to 500 g/ha.
  • the required application rates of herbicides B are generally in the range of from 0.5 to 2500 g/ha and preferably in the range of from 5 to 2000 g/ha, from 100 to 1500 g/h, most preferably from 100 to 500 g/ha of a.s..
  • the required application rates of safeners C are generally in the range of from 0.5 to 2500 g/ha and preferably in the range of from 5 to 2000 g/ha or 10 to 1000 g/ha of a.s..
  • compositions can be employed in a number of crop plants for eliminating undesirable plants.
  • suitable crops are the following: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec, altissima, Beta vulgaris spec, rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var.
  • silvestris Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum,
  • Hevea brasiliensis Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Musa spec, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, S
  • Preferred crops are Arachis hypogaea, Beta vulgaris spec, altissima, Brassica napus var.
  • Especially preferred crops are crops of cereals, corn, soybeans, rice, millets, oilseed rape, cotton, sugarcane, potatoes, legumes, turf or permanent crops.
  • compositions according to the invention can also be used in genetically modified plants.
  • genetically modified plants is to be understood as plants whose genetic material has been modified by the use of recombinant DNA techniques to include an inserted sequence of DNA that is not native to that plant species' genome or to exhibit a deletion of DNA that was native to that species' genome, wherein the modification(s) cannot readily be obtained by cross breeding, mutagenesis or natural recombination alone.
  • a particular genetically modified plant will be one that has obtained its genetic modification(s) by inheritance through a natural breeding or propagation process from an ancestral plant whose genome was the one directly treated by use of a recombinant DNA technique.
  • one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
  • Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides, e. g., by inclusion therein of amino acid mutation(s) that permit, decrease, or promote glycosylation or polymer additions such as prenylation, acetylation farnesylation, or PEG moiety attachment.
  • auxinic herbicides such as
  • herbicides as a result of conventional methods of breeding or genetic engineering; furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxinic herbicides, or ACCase inhibitors.
  • RoundupReady® (glyphosate tolerant, Monsanto, USA), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate tolerant, Bayer CropScience, Germany).
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as delta-endotoxins, e.
  • VIP vegetative insecticidal proteins
  • VIP1 e.g., VIP1 , VIP2, VIP3 or VIP3A
  • insecticidal proteins of bacteria colonizing nematodes e. g., Photorhabdus spp.
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins produced by fungi such as Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors
  • ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3- hydroxy-steroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase
  • ion channel blockers such as blockers of sodium
  • these insecticidal proteins or toxins are to be understood expressly also as including pre-toxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a new combination of protein domains, (see, e. g., WO 02/015701 ).
  • Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073.
  • Plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the CrylAb toxin), YieldGard® Plus (corn cultivars producing CrylAb and Cry3Bb1 toxins),
  • Starlink® corn cultivars producing the Cry9c toxin
  • Herculex® RW corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]
  • NuCOTN® 33B cotton cultivars producing the CrylAc toxin
  • Bollgard® I cotton cultivars producing the CrylAc toxin
  • Bollgard® II cotton cultivars producing CrylAc and Cry2Ab2 toxins
  • VIPCOT® cotton cultivars producing a VIP-toxin
  • NewLeaf® potato cultivars producing the Cry3A toxin
  • Bt-Xtra® NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt1 1 (e.
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called
  • pathogenesis-related proteins PR proteins, see, e.g., EP-A 392 225
  • plant disease resistance genes e. g., potato culti-vars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato, Solanum bulbocastanum
  • T4-lyso-zym e.g., potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylovora.
  • the methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e.g., in the publications mentioned above.
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g., bio-mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • productivity e.g., bio-mass production, grain yield, starch content, oil content or protein content
  • tolerance to drought e.g., salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve human or animal nutrition, e. g., oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g., Nexera® rape, Dow AgroSciences, Canada).
  • a modified amount of ingredients or new ingredients specifically to improve human or animal nutrition, e. g., oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g., Nexera® rape, Dow AgroSciences, Canada).
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
  • a modified amount of ingredients or new ingredients specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
  • compositions according to the invention are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable.
  • crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton
  • compositions have been found for the desiccation and/or defoliation of plants, processes for preparing these compositions, and methods for desiccating and/or defoliating plants using the compositions according to the invention.
  • compositions according to the invention are suitable in particular for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.

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Abstract

The present invention relates to herbicidal compositions comprising at least one isoxazolo[5,4-b]pyridine herbicide I.A, I.B or I.C, or an N-oxide, or an agriculturally useful salt thereof, and at least one further compound selected from herbicidally active compounds of the formula II.1 and II.2, or an N-oxide, or an agriculturally useful salt thereof, and, if desired, a safener C or at least one further herbicide D. The present invention also relates to the use of such a composition for controlling unwanted vegetation and to a method for controlling unwanted vegetation, which comprises allowing a composition to act on plants, their seeds and/or their habitat.

Description

Herbicidal compositions comprising isoxazolo[5,4-b]pyridines
The present invention relates to herbicidal compositions comprising at least one isoxazolo[5,4- b]pyridine herbicide I .A, I.B or I.C, or an N-oxide, or an agriculturally useful salt thereof, and at least one further compound selected from herbicidally active compounds of the formula 11.1 and II.2, or an N-oxide, or an agriculturally useful salt thereof, and, if desired, a safener C or at least one further herbicide D. The present invention also relates to the use of such a composition for controlling unwanted vegetation and to a method for controlling unwanted vegetation, which comprises allowing a composition to act on plants, their seeds and/or their habitat.
In crop protection compositions it is desirable to increase the specific activity of an active compound and the reliability of the effect. It is particularly desirable for the crop protection composition to control the harmful plants effectively, but at the same time to be compatible with the useful plants in question. It is also desirable to provide a broad spectrum of activity allowing the simultaneous control of a variety of harmful plants. Frequently this cannot be achieved using a single herbicidally active compound. With many highly effective herbicides, there is the problem that their compatibility with useful plants, in particular dicotyledonous crop plants, such as cotton, oilseed rape and graminaceous plants, such as barley, millet, corn, rice, wheat and sugar cane, is not always satisfactory, i.e. in addition to the harmful plants, the crop plants, too, are damaged on a scale which cannot be tolerated. By reducing the application rates, the useful plants are spared; however, naturally, the extent of the control of harmful plants decreases too. Frequently, it is a problem that herbicides can only be applied within a narrow time frame in order to achieve the desired herbicidal action, which time frame may be unpredictably influenced by weather conditions. It is known that special combinations of different specifically active herbicides may result in enhanced activity of an herbicide component in the sense of a synergistic effect. In this manner, it may be feasible to reduce the application rates of herbicidally active compounds required for controlling the harmful plants. Furthermore, it is known that in some cases joint application of specifically acting herbicides with organic active compounds, some of which may also have herbicidal activity, provides better crop plant compatibility. In these cases, the active compounds act as antidotes or antagonists and are also referred to as safeners, since they reduce or even prevent damage of herbicides to the crop plants.
Herbicidal isoxazolo[5,4-b]pyridines of formulae I .A, I.B and I.C and their synthesis are known from WO 2012/010633 A1. Routes for the synthesis of isoxazolo[5,4-b]pyridine compounds are known from Elbannany et al, Pharmazie (1988), 43(2), 128-129 and Volochnyuk et al, Journal of Combinatorial Chemistry (2010), 12(4), 510-517. The isoxazolo[5,4-b]pyridine of formula I .A was described in herbicidal compositions with other herbicides and/or safeners in WO
2015/155236. The compounds of the formula 11.1 , their synthesis and mixtures with other herbicides and/or safeners are known from WO 2016/162265 A1 and references cited therein. Compounds of the formula II.2, their synthesis and mixtures with other herbicides and/or safeners are known from WO 2016/156241 A1 and references cited therein.
It is an object of the present invention to provide herbicidal compositions, which are highly active against unwanted harmful plants, showing enhanced activity in the sense of a synergistic effect. At the same time of application the compositions should have good compatibility with useful plants. In addition, the compositions according to the invention should have a broad spectrum of activity. These and further objects are achieved by the herbicidal compositions below.
Accordingly, the present invention relates to herbicidal compositions comprising as component A) at least nsisting of
Figure imgf000003_0001
I.C
or an N-oxide, or an agriculturally useful salt thereof; and as component
B) at least one herbicide of the formula 11.1 , or an N-oxide, or an agriculturally useful salt thereof
Figure imgf000003_0002
wherein R1 is methyl or methoxy; R2 is hydrogen, methyl or ethoxy; and A is a heteroaryl group, which is unsubstituted or substituted with 1 , 2 or 3 radicals selected from the group consisiting of Ci-C6-alkyl or Ci-C6-haloalkyl;
or a herbicide of the formula 11.2, or an N-oxide, or an agriculturally useful salt thereof
Figure imgf000003_0003
wherein R1 is chlorine, methyl or methoxy; R2 is hydrogen, chlorine, methyl or ethoxy; and A is a heteroaryl group, which is unsubstituted or substituted with 1 , 2 or 3 radicals selected from the group consisiting of Ci-C6-alkyl or Ci-C6-haloalkyl; and, if desired, as component C) safeners.
In the definitions of the variables given above, collective terms are used which are generally representative for the substituents in question. The term "Cn-Cm" indicates the number of carbon atoms possible in each case in the substituent or substituent moiety in question.
As used herein, the terms "controlling" and "combating" are synonyms. As used herein, the terms "undesirable vegetation" and "harmful plants" are synonyms. The term "Ci-C6-alkyl" refers to a straight-chained or branched saturated hydrocarbon group having 1 to 6 carbon atoms, for example methyl, ethyl, propyl, 1 -methylethyl, butyl,
1 -methylpropyl, 2-methylpropyl and 1 ,1 -dimethylethyl.
The term "Ci-C6-haloalkyl" refers to a straight-chained or branched alkyl group having 1 to 6 carbon atoms (as defined above), wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example chloromethyl,
bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl,
1 - fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro- 2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl, 2- fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3- chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3- trichloropropyl, CH2-C2F5, CF2-C2F5, CF(CF3)2, 1 -(fluoromethyl)-2-fluoroethyl, l -(chloromethyl)-
2- chloroethyl, 1 -(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl.
The term "heteroaryl" refers to 5- or 6-membered aromatic ring systems incuding besides carbon atoms, 1 , 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S; for example, a 5-membered heteroaryl such as pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4- oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thiadiazol-5-yl;
or a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
The isoxazolo[5,4-b]pyridine compounds of formula I. A, I.B and I.C and the herbicides of the formula 11.1 and II.2 have ionizable functional groups. They can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.
Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, C1-C4- alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium, tetradecylammonium,
tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2-hydroxyeth-1 -oxy)eth-1 -ylammonium (diglycolamine salt), di(2-hydroxyeth-1 - yl)ammonium (diolamine salt), tris(2-hydroxyethyl)ammonium (trolamine salt), tris(2- hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, Ν,Ν,Ν- trimethylethanolammonium (choline salt), furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium, and finally the salts of polybasic amines such as N,N-bis- (3-aminopropyl)methylamine and diethylenetriamine.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide,
hydrogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
The invention relates in particular to compositions in the form of herbicidally active agrochemical compositions comprising a herbicidally effective amount of an active compound combination comprising at least one isoxazolo[5,4-b]pyridine compound of formula I .A, I.B or I.C, or an N- oxide, or an agriculturally useful salt thereof, and at least one further herbicide selected from a herbicide of the formula 11.1 or II.2, or an N-oxide, or an agriculturally useful salt thereof, and, if desired, safeners C or at least one further herbicide D, and at least one liquid and/or solid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for agrochemical compositions. An agrochemical composition comprises a pesticidally effective amount of at least one composition according to the invention. The term "effective amount" denotes an amount of the active ingredients, which is sufficient for controlling unwanted plants, especially for controlling unwanted plants in cultivated plants and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the plants to be controlled, the treated cultivated plant or material, the climatic conditions and the specific composition according to the invention used. The invention furthermore relates to a method for controlling unwanted vegetation, in particular in fields where crop plants are cultivated. The invention also relates to a method for the desiccation or defoliation of plants.
Surprisingly, the time frame, within which the desired herbicidal action can be achieved, may be expanded by the compositions according to the invention. This allows a more flexibly timed application of the compositons according to the present invention in comparison with the single compounds.
Moreover, the compositions according to the invention have better herbicidal activity, i.e. better activity against harmful plants, than would have been expected based on the herbicidal activity observed for the individual components A or B, or a broader activity spectrum.
The herbicidal activity to be expected for compositions based on the individual compound can be calculated using the method of S. R. Colby (1967) "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, p. 22 ff.. The value E, which represents the expected additive activity of the individual active compounds, was calculated using the formula
E = X + Y - (X Y/100),
wherein
X = percent activity using active component A at an application rate a;
Y = percent activity using active component B at an application rate b;
E = expected activity (in %) by A + B at application rates a + b.
If the value observed experimentally is higher than the value E calculated according to Colby, a synergistic effect is present.
In one embodiment of the invention the compositions comprise as component A isoxazolo[5,4- b]pyridine of formula I .A or an agriculturally acceptable salt thereof.
If the isoxazolo[5,4-b]pyridine compounds of formula I .A. I.B or I.C or the herbicides of the formula 11.1 or II.2, the safeners C or the further herbicides D as described herein, are capable of forming geometrical isomers, it is possible to use both, the pure isomers and mixtures thereof, in the compositions according to the invention.
With regard to the herbicides of component B, preference is given to a specific epimeric form of the formula 11.1 , which is represented by formula II.1 a, wherein the 5-position has an R- configuration and wherein the radicals R1, R2 and A are as defined for compounds of the formula 11.1 .
Figure imgf000006_0001
II.1a
Preference is given to compositions comprising as component B a herbicide selected from the group consisting of
Figure imgf000006_0002
II.A II.C
Figure imgf000006_0003
II.D II.E II.F
Figure imgf000007_0001
or an N-oxide, or an agriculturally useful salt thereof.
Particular preference is given to compositions wherein component A is the compound of the formula I.A and component B is selected from the group consisting of compounds of the formulae II.A, 5S-II.A, N-C, II. D, II. F, II.G, II.H and II.J; in particular component B is 5S-II.A or II. D.
In one aspect of the invention component A is the compound of the formula I.A and component B is selected from the group consisting of compounds of the formulae 4R,5S-II.A, 4S,5S-II.A, II. Ca, II. Cb, II.Fa and II.Fb, or component B is selected from mixtures of these stereoisomers.
Figure imgf000007_0002
ll.Ca ll.Cb II.Fa II.Fb
Figure imgf000008_0001
4R,5S-II.A 4S,5S-II.A
Compound ll.Ca is herein referred to as {4S, 5R)-5-ethoxy-4-hydroxy-1 -methyl-3-[4- (trifluoromethyl)-2-pyridyl]imidazolidin-2-one.
Compound ll.Cb is herein referred to as (4R, 5R)-5-ethoxy-4-hydroxy-1 -methyl-3-[4- (trifluoromethyl)-2-pyridyl]imidazolidin-2-one.
Compound 11. Fa is herein referred to as (4R, 5S)-1 -(5-tert-butylisoxazol-3-yl)-4-ethoxy-5- hydroxy-3-methyl-imidazolidin-2-one.
Compound II.Fb is herein referred to as (4R, 5R)-1 -(5-tert-butylisoxazol-3-yl)-4-ethoxy-5- hydroxy-3-methyl-imidazolidin-2-one.
Compound 4R,5S-II.A is herein referred to as (4R,5SJ-4-hydroxy-1 -methoxy-5-methyl-3-[4- trifluoromethyl)-2-pyridyl]imidazolidin-2-one.
Compunds 4S,5S-II.A is herein referred to as (4S,5SJ-4-hydroxy-1 -methoxy-5-methyl-3-[4- (trifluoromethyl)-2-pyridyl]imidazolidin-2-one.
In one aspect component A is the compound of the formula I.A and component B is selected from the stereoisomers of the compound of the formula II.C, {4R, 5R)-5-ethoxy-4-hydroxy-1 - methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one and (4S, 5R)-5-ethoxy-4-hydroxy-1 - methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, or mixtures of these stereoisomers.
In a further aspect component A is the compound of the formula I.A and component B is selected from the stereoisomers of the compound of the formula II. F, (4R, 5R)-1 -(5-tert- butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one and (4R, 5S)-1 -(5-tert- butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one, or mixtures of these stereoisomers.
In another aspect component A is the compound of the formula I.A and component B is selected from the stereoisomers of the compound of the formula 11. A, (4R,5S,)-4-hydroxy-1 - methoxy-5-methyl-3-[4-trifluoromethyl)-2-pyridyl]imidazolidin-2-one and (4S,5S J-4-hydroxy-l - methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, or mixtures of these stereoisomers.
Further embodiments relate to ternary compositions which correspond to the binary compositions mentioned above and additionally comprise a safener C. Particularly preferred safeners C, namely C.1 to C.17, are listed below in table C.
Table C
Safener C C.4 cyprosulfamide
C.1 benoxacor C.5 dichlormid
C.2 cloquintocet C.6 fenchlorazole
C.3 cloquintocet-mexyl C.7 fenchlorazole-ethyl C.8 fenclorim C.13 mefenpyr-diethyl
C.9 furilazole C.14 naphtalic acid anhydride
C.10 isoxadifen C.15 4-(dichloroacetyl)-1 -oxa-4-
C.1 1 isoxadifen-ethyl C.16 2,2,5-trimethyl-3-(dichloro-
C.12 mefenpyr C.17 N-(2-Methoxybenzoyl)-4-
Safeners C are known from, for example, The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Science Society of America, 1998.
The compositions according to the invention may comprise further herbicides D selected from the group consisiting of pinoxaden, clethodim, clodinafop-propargyl, chlorsulfuron, florasulam, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, mesosulfuron-methyl, metazosulfuron, metsulfuron-methyl, nicosulfuron, penoxsulam, pyroxsulam,thiencarbazone-methyl,
thifensulfuron-methyl, tribenuron-methyl, atrazine, bentazon, bromoxynil, metribuzin, paraquat-, ichloride, acifluorfen, carfentrazone-ethyl, flumioxazin, fomesafen, oxadiargyl, oxyfluorfen, saflufenacil , sulfentrazone, trifludimoxazin, isoxaflutole, mesotrione, tembotrione, topramezone, topramezone-sodium, bicyclopyrone, fenquinotrione, glyphosate, glufosinate, acetochlor, pendimethalin, metolachlor, S-metolachlor, pyroxasulfone, dimethanamid, dicamba, fluroxypyr, 2,4-D, MCPA, quinclorac, diflufenzopyr, pyridate, halauxifen and their agriculturally acceptable salts and derivatives.
In a preferred aspect the compositions may comprise further herbicides D selected from the group consisting of atrazine, terbutylazine, mesotrione, bicyclopyron, S-metolachlor,
topramezone, dicamba, bentazone, DMTA-p, pyroxasulfone, pendimethylin, atrazine, mesotrione and bicyclopyrone.
Further herbicides D and safeners C having a carboxyl group can be employed in the form of the acid or in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative in the compositions according to the invention.
In the case of dicamba, suitable salts include those, where the counterion is an agriculturally acceptable cation. For example, suitable salts of dicamba are dicamba-sodium, dicamba- potassium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba- isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicamba- trolamine, dicamba-N,N-bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine. Examples of a suitable ester are dicamba-methyl and dicamba-butotyl.
Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D- diethylammonium, 2,4-D-diethanolammonium (2,4-D-diolamine), 2,4-D-triethanolammonium, 2,4-D-isopropylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D- dodecylammonium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2- hydroxypropyl)ammonium, 2,4-D-tris(isopropyl)ammonium, 2,4-D-trolamine, 2,4-D-lithium, 2,4- D-sodium. Examples of suitable esters of 2,4-D are 2,4-D-butotyl, 2,4-D-2-butoxypropyl, 2,4-D- 3-butoxypropyl, 2,4-D-butyl, 2,4-D-ethyl, 2,4-D-ethylhexyl, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D- isopropyl, 2,4-D-meptyl, 2,4-D-methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl and clacyfos.
Suitable salts of 2,4-DB are for example 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB- dimethylammonium. Suitable esters of 2,4-DB are for example 2,4-DB-butyl and 2,4-DB-isoctyl. Suitable salts of dichlorprop are for example dichlorprop-sodium, dichlorprop-potassium and dichlorprop-dimethylammonium. Examples of suitable esters of dichlorprop are dichlorprop- butotyl and dichlorprop-isoctyl.
Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl, MCPA-dimethyl- ammonium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA- isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA- olamine, MCPA-potassium, MCPA-sodium and MCPA-trolamine.
A suitable salt of MCPB is MCPB sodium. A suitable ester of MCPB is MCPB-ethyl.
Suitable salts of clopyralid are clopyralid-potassium, clopyralid-olamine and clopyralid-tris-(2- hydroxypropyl)ammonium. Example of suitable esters of clopyralid is clopyralid-methyl.
Examples of a suitable ester of fluroxypyr are fluroxypyr-meptyl and fluroxypyr-2-butoxy-1 - methylethyl, wherein fluroxypyr-meptyl is preferred.
Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram- triisopropanolammonium, picloram-triisopropylammonium and picloram-trolamine. A suitable ester of picloram is picloram-isoctyl.
A suitable salt of triclopyr is triclopyr-triethylammonium. Suitable esters of triclopyr are for example triclopyr-ethyl and triclopyr-butotyl.
Suitable salts and esters of chloramben include chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium and chloramben-sodium. Suitable salts and esters of 2,3,6-TBA include 2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA- potassium and 2,3,6-TBA-sodium.
Suitable salts and esters of aminopyralid include aminopyralid-potassium, aminopyralid- dimethylammonium, and aminopyralid-tris(2-hydroxypropyl)ammonium.
Suitable salts of glyphosate are for example glyphosate-ammonium, glyphosate-diammonium, glyphoste-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-trimesium as well as the ethanolamine and diethanolamine salts, preferably glyphosate-diammonium, glyphosate-isopropylammonium and glyphosate- trimesium (sulfosate).
A suitable salt of glufosinate is for example glufosinate-ammonium.
A suitable salt of glufosinate-P is for example glufosinate-P-ammonium.
Suitable salts and esters of bromoxynil are for example bromoxynil-butyrate, bromoxynil- heptanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.
Suitable salts and esters of ioxonil are for example ioxonil-octanoate, ioxonil-potassium and ioxonil-sodium.
Suitable salts and esters of mecoprop include mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop- methyl, mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.
Suitable salts of mecoprop-P are for example mecoprop-P-butotyl, mecoprop-P- dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P-sodium.
A suitable salt of diflufenzopyr is for example diflufenzopyr-sodium.
A suitable salt of naptalam is for example naptalam-sodium.
Suitable salts and esters of aminocyclopyrachlor are for example aminocyclopyrachlor- dimethylammonium, aminocyclopyrachlor-methyl, aminocyclopyrachlor- triisopropanolammonium, aminocyclopyrachlor-sodium and aminocyclopyrachlor-potassium. A suitable salt of quinclorac is for example quinclorac-dimethylammonium.
A suitable salt of quinmerac is for example quinmerac-dimethylammonium.
A suitable salt of imazamox is for example imazamox-ammonium.
Suitable salts of imazapic are for example imazapic-ammonium and imazapic- isopropylammonium.
Suitable salts of imazapyr are for example imazapyr-ammonium and imazapyr- isopropylammonium.
A suitable salt of imazaquin is for example imazaquin-ammonium.
Suitable salts of imazethapyr are for example imazethapyr-ammonium and imazethapyr- isopropylammonium.
A suitable salt of topramezone is for example topramezone-sodium.
The term "binary compositions" refers to compositions comprising one or more isoxazolo[5,4- b]pyridines of the formula I .A, I.B or I.C (component A), and one or more herbicides of the formula 11.1 or II.2 or subformulae thereof as defined herein (component B).
The term "ternary compositions" refers to compositions comprising one or more isoxazolo[5,4- b]pyridines of the formula I.A, I.B or I.C (component A), and one or more, herbicides of the formula 11.1 or II.2 or subformulae thereof as defined herein (component B), and a third component, which may be a further herbicide D as defined herein or one or more safeners C as defined herein.
In binary compositions the weight ratio of the active components A:B is generally in the range of from 1 :500 to 500:1 , or in the range of from 1 :250 to 250:1 , or in the range of from 1 :125 to 125:1 , or in the range of from 1 :50 to 50: 1 , or in the range of from 1 :20 to 20: 1 , or in the range of from 1 :5 to 5:1 .
In one preferred embodiment the weight ratio of the active components I.A:B is in the range of from 1 :10 to 10:1 or more preferably from 1 :5 to 5:1 , in a specially preferred embodiment 1 :3 to 3:1 , for example 1 :1 , 1 .5:1 , 2:1 , 1 :1.5 or 1 :2.
In ternary compositions the relative proportions by weight of the components A:B are generally in the range of from 1 :500 to 500:1 , or in the range of from 1 :250 to 250:1 , or in the range of from 1 :125 to 125:1 , or the range of from 1 :50 to 50:1 , or in the range of from 1 :20 to 20:1 , or in the range of from 1 :5 to 5:1 ; and wherein the weight ratio of the components A:C or A:D is generally in the range of from 1 :500 to 500:1 , or in the range of from 1 :250 to 250:1 , or in the range of from 1 :125 to 125:1 , or the range of from 1 :50 to 50:1 , or in the range of from 1 :20 to 20:1 , or in the range of from 1 :5 to 5:1 ; and the weight ratio of the components B:C is generally in the range of from 1 :500 to 500:1 , or in the range of from 1 :250 to 250:1 , or in the range of from 1 : 125 to 125: 1 , or the range of from 1 :50 to 50: 1 , or in the range of from 1 :20 to 20: 1 , or in the range of from 1 :5 to 5:1 . The weight ratio of components A + B to component C or D is preferably in in the range of from 1:250 to 250:1, in particular in the range of from 1:50 to 50:1 and particularly preferably in the range of from 1:10 to 10:1.
The weight ratios of the individual components in the preferred compositions mentioned below are within the limits given above, in particular within the preferred limits.
Particularly preferred are the compositions mentioned below in table 1 , wherein each
composition comprises isoxazolo[5,4-b]pyridine of formula I.A, a component B and, if desired, the safener C as defined for each individual composition in one row of table 1 below
(compositions no. M1.1 to M1.270).
Also preferred are compositions M2.1 to M2.270, which differ from the corresponding
compositions M1.1 to M1.270 in table 1 only in that they comprise as the active component A, instead of the isoxazolo[5,4-b]pyridine of formula I.A, the isoxazolo[5,4-b]pyridine of formula I.B. Also preferred are compositions M3.1 to M3.270, which differ from the corresponding
compositions M1.1 to M1.270 in table 1 only in that they comprise as the active component A, instead of the isoxazolo[5,4-b]pyridine of formula I.A, the isoxazolo[5,4-b]pyridine of formula I.C. The specific number for each single composition is deductible as follows: for example, composition M1.18 comprises the compound of the formula I.A, the compound of the formula 4S,5S-II.A and the safener C.1 (benoxacor, as defined in table C).
Table 1:
M1.1: I.A+II.A; M1.2: I.A+4R.5S-II.A; M1.3: I.A+4S.5S-II.A; M1.4: I.A+II.B; M1.5: I.A+II.Ca; M1.6: I.A+II.Cb; M1.7: I.A+II.D; M1.8: I.A+II.E; M1.9: I.A+II.Fa; M1.10: I.A+II.Fb; M1.11: I.A+II.G;
M1.12: I.A+II.H; M1.13: I.A+II.J; M1.14: I.A+II.K; M1.15: I.A+II.L; M1.16: I.A+II.A+C.1; M1.17: I.A+4R,5S-II.A+C1; M1.18: I.A+4S,5S-II.A+C1; M1.19: I.A+II.B+C.1; M1.20: I.A+II.Ca+C.1; M1.21: I.A+II.Cb+C.1; M1.22: I.A+II.D+C.1; M1.23: I.A+II.E+C.1; M1.24: I.A+II.Fa+C.1; M1.25: I.A+II.Fb+C.1; M1.26: I.A+II.G+C.1; M1.27: I.A+II.H+C.1; M1.28: I.A+II.J+C.1; M1.29:
I.A+II.K+C.1; M1.30: I.A+II.L+C.1; M1.31: I.A+II.A+C.2; M1.32: I.A+4R,5S-II.A+C.2; M1.33: I.A+4S,5S-II.A+C2; M1.34: I.A+II.B+C.2; M1.35: I.A+II.Ca+C.2; M1.36: I.A+II.Cb+C.2; M1.37: I.A+II.D+C.2; M1.38: I.A+II.E+C.2; M1.39: I.A+II.Fa+C.2; M1.40: I.A+II.Fb+C.2; M1.41:
I.A+II.G+C.2; M1.42: I.A+II.H+C.2; M1.43: I.A+II.J+C.2; M1.44: I.A+II.K+C.2; M1.45:
I.A+II.L+C.2; M1.46: I.A+II.A+C.3; M1.47: I.A+4R,5S-II.A+C3; M1.48: I.A+4S,5S-II.A+C3;
M1.49: I.A+II.B+C.3; M1.50: I.A+II.Ca+C.3; M1.51: I.A+II.Cb+C.3; M1.52: I.A+II.D+C.3; M1.53: I.A+II.E+C.3; M1.54: I.A+II.Fa+C.3; M1.55: I.A+II.Fb+C.3; M1.56: I.A+II.G+C.3; M1.57:
I.A+II.H+C.3; M1.58: I.A+II.J+C.3; M1.59: I.A+II.K+C.3; M1.60: I.A+II.L+C.3; M1.61:
I.A+II.A+C.4; M1.62: I.A+4R,5S-II.A+C4; M1.63: I.A+4S,5S-II.A+C4; M1.64: I.A+II.B+C.4; M1.65: I.A+II.Ca+C.4; M1.66: I.A+II.Cb+C.4; M1.67: I.A+II.D+C.4; M1.68: I.A+II.E+C.4; M1.69: I.A+II.Fa+C.4; M1.70: I.A+II.Fb+C.4; M1.71: I.A+II.G+C.4; M1.72: I.A+II.H+C.4; M1.73:
I. A+II.J+C.4; M1.74: I.A+II.K+C.4; M1.75: I.A+II.L+C.4; M1.76: I.A+II.A+C.5; M1.77: I.A+4R.5S-
II. A+C.5; M1.78: I.A+4S,5S-II.A+C.5; M1.79: I.A+II.B+C.5; M1.80: I.A+II.Ca+C.5; M1.81:
I.A+II.Cb+C.5; M1.82: I.A+II.D+C.5; M1.83: I.A+II.E+C.5; M1.84: I.A+II.Fa+C.5; M1.85:
I.A+II.Fb+C.5; M1.86: I.A+II.G+C.5; M1.87: I.A+II.H+C.5; M1.88: I.A+II.J+C.5; M1.89:
I.A+II.K+C.5; M1.90: I.A+II.L+C.5; M1.91 : I.A+II.A+C.6; M1.92: I.A+4R,5S-II.A+C6; M1.93: I.A+4S,5S-II.A+C6; M1.94: I.A+II.B+C.6; M1.95: I.A+II.Ca+C.6; M1.96: I.A+II.Cb+C.6; M1.97: I.A+II.D+C.6; M1.98: I.A+II.E+C.6; M1.99: I.A+II.Fa+C.6; M1.100: I.A+II.Fb+C.6; M1.101: I.A+II.G+C.6; M1.102: I.A+II.H+C.6; M1.103: I.A+II.J+C.6; M1.104: I.A+II.K+C.6; M1.105:
I.A+II.L+C.6; M1.106: I.A+II.A+C.7; M1.107: I.A+4R.5S-II.A+C.7; M1.108: I.A+4S,5S-II.A+C7; M1.109: I.A+II.B+C.7; M1.110: I.A+II.Ca+C.7; M1.111: I.A+II.Cb+C.7; M1.112: I.A+II.D+C.7; M1.113: I.A+II.E+C.7; M1.114: I.A+II.Fa+C.7; M1.115: I.A+II.Fb+C.7; M1.116: I.A+II.G+C.7; M1.117: I.A+II.H+C.7; M1.118: I.A+II.J+C.7; M1.119: I.A+II.K+C.7; M1.120: I.A+II.L+C.7;
M1.121: I.A+II.A+C.8; M1.122: I.A+4R.5S-II.A+C.8; M1.123: I.A+4S,5S-II.A+C8; M1.124: I.A+II.B+C.8; M1.125: I.A+II.Ca+C.8; M1.126: I.A+II.Cb+C.8; M1.127: I.A+II.D+C.8; M1.128: I.A+II.E+C.8; M1.129: I.A+II.Fa+C.8; M1.130: I.A+II.Fb+C.8; M1.131: I.A+II.G+C.8; M1.132: I.A+II.H+C.8; M1.133: I.A+II.J+C.8; M1.134: I.A+II.K+C.8; M1.135: I.A+II.L+C.8; M1.136:
I.A+II.A+C.9; M1.137: I.A+4R,5S-II.A+C9; M1.138: I.A+4S,5S-II.A+C.9; M1.139: I.A+II.B+C.9; M1.140: I.A+II.Ca+C.9; M1.141: I.A+II.Cb+C.9; M1.142: I.A+II.D+C.9; M1.143: I.A+II.E+C.9; M1.144: I.A+II.Fa+C.9; M1.145: I.A+II.Fb+C.9; M1.146: I.A+II.G+C.9; M1.147: I.A+II.H+C.9; M1.148: I.A+II.J+C.9; M1.149: I.A+II.K+C.9; M1.150: I.A+II.L+C.9; M1.151: I.A+II.A+C.10; M1.152: I.A+4R,5S-II.A+C10; M1.153: I.A+4S,5S-II.A+C.10; M1.154: I.A+II.B+C.10; M1.155: I.A+II.Ca+C.10; M1.156: I.A+II.Cb+C.10; M1.157: I.A+II.D+C.10; M1.158: I.A+II.E+C.10;
M1.159: I.A+II.Fa+C.10; M1.160: I.A+II.Fb+C.10; M1.161: I.A+II.G+C.10; M1.162:
I.A+II.H+C.10; M1.163: I.A+II.J+C.10; M1.164: I.A+II.K+C.10; M1.165: I.A+II.L+C.10; M1.166: I.A+II.A+C.11; M1.167: I.A+4R,5S-II.A+C11 ; M1.168: I.A+4S,5S-II.A+C11 ; M1.169:
I.A+II.B+C.11; M1.170: I.A+II.Ca+C.11 ; M1.171: I.A+II.Cb+C.11 ; M1.172: I.A+II.D+C.11;
M1.173: I.A+II.E+C.11 ; M1.174: I.A+II.Fa+C.11 ; M1.175: I.A+II.Fb+C.11 ; M1.176:
I.A+II.G+C.11; M1.177: I.A+II.H+C.11 ; M1.178: I.A+II.J+C.11; M1.179: I.A+II.K+C.11 ; M1.180:
I. A+II.L+C.11; M1.181: I.A+II.A+C.12; M1.182: I.A+4R,5S-II.A+C12; M1.183: I.A+4S,5S-
II. A+C.12; M1.184: I.A+II.B+C.12; M1.185: I.A+II.Ca+C.12; M1.186: I.A+II.Cb+C.12; M1.187: I.A+II.D+C.12; M1.188: I.A+II.E+C.12; M1.189: I.A+II.Fa+C.12; M1.190: I.A+II.Fb+C.12;
M1.191: I.A+II.G+C.12; M1.192: I.A+II.H+C.12; M1.193: I.A+II.J+C.12; M1.194: I.A+II.K+C.12; M1.195: I.A+II.L+C.12; M1.196: I.A+II.A+C.13; M1.197: I.A+4R,5S-II.A+C13; M1.198:
I.A+4S,5S-II.A+C13; M1.199: I.A+II.B+C.13; M1.200: I.A+II.Ca+C.13; M1.201: I.A+II.Cb+C.13; M1.202: I.A+II.D+C.13; M1.203: I.A+II.E+C.13; M1.204: I.A+II.Fa+C.13; M1.205:
I.A+II.Fb+C.13; M1.206: I.A+II.G+C.13; M1.207: I.A+II.H+C.13; M1.208: I.A+II.J+C.13; M1.209: I.A+II.K+C.13; M1.210: I.A+II.L+C.13; M1.211: I.A+II.A+C.14; M1.212: I.A+4R,5S-II.A+C14; M1.213: I.A+4S,5S-II.A+C14; M1.214: I.A+II.B+C.14; M1.215: I.A+II.Ca+C.14; M1.216:
I.A+II.Cb+C.14; M1.217: I.A+II.D+C.14; M1.218: I.A+II.E+C.14; M1.219: I.A+II.Fa+C.14;
M1.220: I.A+II.Fb+C.14; M1.221: I.A+II.G+C.14; M1.222: I.A+II.H+C.14; M1.223: I.A+II.J+C.14; M1.224: I.A+II.K+C.14; M1.225: I.A+II.L+C.14; M1.226: I.A+II.A+C.15; M1.227: I.A+4R,5S- II.A+C.15; M1.228: I.A+4S,5S-II.A+C15; M1.229: I.A+II.B+C.15; M1.230: I.A+II.Ca+C.15; M1.231: I.A+II.Cb+C.15; M1.232: I.A+II.D+C.15; M1.233: I.A+II.E+C.15; M1.234:
I.A+II.Fa+C.15; M1.235: I.A+II.Fb+C.15; M1.236: I.A+II.G+C.15; M1.237: I.A+II.H+C.15;
M1.238: I.A+II.J+C.15; M1.239: I.A+II.K+C.15; M1.240: I.A+II.L+C.15; M1.241: I.A+II.A+C.16; M1.242: I.A+4R,5S-II.A+C16; M1.243: I.A+4S,5S-II.A+C16; M1.244: I.A+II.B+C.16; M1.245: I.A+II.Ca+C.16; M1.246: I.A+II.Cb+C.16; M1.247: I.A+II.D+C.16; M1.248: I.A+II.E+C.16;
M1.249: I .A+l I .Fa+C.16; M1.250: I.A+II.Fb+C.16; M1.251: I.A+II.G+C.16; M1.252:
I.A+II.H+C.16; M1.253: I.A+II.J+C.16; M1.254: I.A+II.K+C.16; M1.255: I.A+II.L+C.16; M1.256: I.A+II.A+C.17; M1.257: I.A+4R,5S-II.A+C17; M1.258: I.A+4S,5S-II.A+C17; M1.259: I.A+II.B+C.17; M1.260: I.A+II.Ca+C.17; M1 .261 : I.A+II.Cb+C.17; M1 .262: I.A+II.D+C.17;
M1 .263: I.A+II.E+C.17; M1.264: I.A+II.Fa+C.17; M1.265: I.A+II.Fb+C.17; M1.266:
I.A+II.G+C.17; M1.267: I.A+II.H+C.17; M1 .268: I.A+II.J+C.17; M1.269: I.A+II.K+C.17; M1.270: I.A+II.L+C.17.
Also especially preferred are compositions M4.1 to M4.270, which differ from the corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise pinoxaden as further herbicide D.
Also especially preferred are compositions M5.1 to M5.270, which differ from the corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise clethodim as further herbicide D.
Also especially preferred are compositions M6.1 to M6.270, which differ from the corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise clodinafop-propargyl as further herbicide D.
Also especially preferred are compositions M7.1 to M7.270, which differ from the corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise chlorsulfuron as further herbicide D.
Also especially preferred are compositions M8.1 to M8.270, which differ from the corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise florasulam as further herbicide D.
Also especially preferred are compositions M9.1 to M9.270, which differ from the corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise imazamox as further herbicide D.
Also especially preferred are compositions M10.1 to M10.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise imazapic as further herbicide D.
Also especially preferred are compositions M1 1.1 to M1 1 .270, which differ from the
corresponding compositions M1.1 to M1 .270 only in that they additionally comprise imazapyr as further herbicide D.
Also especially preferred are compositions M12.1 to M12.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise imazaquin as further herbicide D.
Also especially preferred are compositions M13.1 to M13.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise imazethapyr as further herbicide D.
Also especially preferred are compositions M14.1 to M14.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise
mesosulfuron-methyl as further herbicide D.
Also especially preferred are compositions M15.1 to M15.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise
metazosulfuron as further herbicide D.
Also especially preferred are compositions M16.1 to M16.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise metsulfuron- methyl as further herbicide D.
Also especially preferred are compositions M17.1 to M17.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise nicosulfuron as further herbicide D.
Also especially preferred are compositions M18.1 to M18.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise penoxsulam as further herbicide D.
Also especially preferred are compositions M19.1 to M19.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise pyroxsulam as further herbicide D.
Also especially preferred are compositions M20.1 to M20.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise
thiencarbazone-methyl as further herbicide D.
Also especially preferred are compositions M21.1 to M21 .270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise
thifensulfuron-methyl as further herbicide D.
Also especially preferred are compositions M22.1 to M22.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise tribenuron- methyl as further herbicide D.
Also especially preferred are compositions M23.1 to M23.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise atrazine as further herbicide D.
Also especially preferred are compositions M5.1 to M5.270, which differ from the corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise bentazon as further herbicide D.
Also especially preferred are compositions M24.1 to M24.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise bromoxynil as further herbicide D.
Also especially preferred are compositions M25.1 to M25.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise metribuzin as further herbicide D.
Also especially preferred are compositions M26.1 to M26.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise paraquat- dichloride as further herbicide D.
Also especially preferred are compositions M27.1 to M27.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise acifluorfen as further herbicide D.
Also especially preferred are compositions M28.1 to M28.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise
carfentrazone-ethyl as further herbicide D.
Also especially preferred are compositions M29.1 to M29.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise flumioxazin as further herbicide D. Also especially preferred are compositions M30.1 to M30.270, which differ from the corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise fomesafen as further herbicide D.
Also especially preferred are compositions M31.1 to M31 .270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise oxadiargyl as further herbicide D.
Also especially preferred are compositions M32.1 to M32.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise oxyfluorfen as further herbicide D.
Also especially preferred are compositions M33.1 to M33.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise saflufenacil as further herbicide D.
Also especially preferred are compositions M34.1 to M34.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise
sulfentrazone as further herbicide D.
Also especially preferred are compositions M35.1 to M35.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise isoxaflutole as further herbicide D.
Also especially preferred are compositions M36.1 to M36.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise mesotrione as further herbicide D.
Also especially preferred are compositions M37.1 to M37.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise tembotrione as further herbicide D.
Also especially preferred are compositions M38.1 to M38.270, which differ from the
corresponding compositions M1.1 to M1 .270 only in that they additionally comprise
topramezone as further herbicide D.
Also especially preferred are compositions M39.1 to M39.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise
topramezone-sodium as further herbicide D.
Also especially preferred are compositions M40.1 to M40.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise
bicyclopyrone as further herbicide D.
Also especially preferred are compositions M41.1 to M41 .270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise
fenquinotrione as further herbicide D.
Also especially preferred are compositions M42.1 to M42.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise glyphosate as further herbicide D.
Also especially preferred are compositions M43.1 to M43.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise glufosinate as further herbicide D.
Also especially preferred are compositions M44.1 to M44.270, which differ from the corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise acetochlor as further herbicide D.
Also especially preferred are compositions M45.1 to M45.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise
pendimethalin as further herbicide D.
Also especially preferred are compositions M46.1 to M46.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise metolachlor as further herbicide D.
Also especially preferred are compositions M47.1 to M47.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise S- metolachlor as further herbicide D.
Also especially preferred are compositions M48.1 to M48.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise
pyroxasulfone as further herbicide D.
Also especially preferred are compositions M49.1 to M49.270, which differ from the
corresponding compositions M1.1 to M1 .270 only in that they additionally comprise
dimethanamid as further herbicide D.
Also especially preferred are compositions M50.1 to M50.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise dicamba as further herbicide D.
Also especially preferred are compositions M51.1 to M51 .270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise fluroxypyr as further herbicide D.
Also especially preferred are compositions M52.1 to M52.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise 2,4-D as further herbicide D.
Also especially preferred are compositions M53.1 to M53.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise MCPA as further herbicide D.
Also especially preferred are compositions M54.1 to M54.270, which differ from the
corresponding compositions M1.1 to M1 .270 only in that they additionally comprise quinclorac as further herbicide D.
Also especially preferred are compositions M55.1 to M55.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise
diflufenzopyr as further herbicide D.
Also especially preferred are compositions M56.1 to M56.270, which differ from the
corresponding compositions M1.1 to M1 . 34 only in that they additionally comprise pyridate as further herbicide D.
Also especially preferred are compositions M57.1 to M57.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise halauxifen as further herbicide D.
Also especially preferred are compositions M58.1 to M58.270, which differ from the
corresponding compositions M1 .1 to M1 .270 only in that they additionally comprise trifludimoxazin as further herbicide D.
The components A and B, and, optionally, a safener or a further herbicide D, their N-oxides, salts or derivatives can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for agrochemical composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further agrochemical compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.
The agrochemical compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants,
compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,
tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid
alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.
Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water- soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron
hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants). Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
Examples for agrochemical composition types and their preparation are:
i) Water-soluble concentrates (SL, LS) 10-60 wt% of a compostion according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) ad 100 wt%. The active substance dissolves upon dilution with water.
ii) Dispersible concentrates (DC)
5-25 wt% of a composition according to the invention and 1 -10 wt% dispersant (e. g.
polyvinylpyrrolidone) are dissolved in organic solvent (e.g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion.
iii) Emulsifiable concentrates (EC)
15-70 wt% of a composition according to the invention and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion.
iv) Emulsions (EW, EO, ES)
5-40 wt% of a composition according to the invention and 1 -10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
v) Suspensions (SC, OD, FS)
In an agitated ball mill, 20-60 wt% of a composition according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1 -2 wt% thickener (e.g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.
vi) Water-dispersible granules and water-soluble granules (WG, SG)
50-80 wt% of a composition according to the invention are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)
50-80 wt% of a composition according to the invention are ground in a rotor-stator mill with addition of 1 -5 wt% dispersants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g. alcohol ethoxylate) and solid carrier (e.g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.
viii) Gel (GW, GF)
In an agitated ball mill, 5-25 wt% of a composition according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1 -5 wt% thickener (e.g. carboxymethylcellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance. ix) Microemulsion (ME)
5-20 wt% of a composition according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
x) Microcapsules (CS)
An oil phase comprising 5-50 wt% of a composition according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g.
methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g.
diphenylmethene-4,4'-diisocyanate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1 -10 wt%. The wt% relate to the total CS composition.
xi) Dustable powders (DP, DS)
1 -10 wt% of a composition according to the invention are ground finely and mixed intimately with solid carrier (e.g. finely divided kaolin) ad 100 wt%.
xii) Granules (GR, FG)
0.5-30 wt% of a composition according to the invention is ground finely and associated with solid carrier (e.g. silicate) ad 100 wt%. Granulation is achieved by extrusion, spray-drying or the fluidized bed.
xiii) Ultra-low volume liquids (UL)
1 -50 wt% of a composition according to the invention are dissolved in organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%.
The agrochemical composition types i) to xiii) may optionally comprise further auxiliaries, such as 0,1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1 -1 wt% anti-foaming agents, and 0,1 -1 wt% colorants.
The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
Solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before or during sowing.
Methods for applying compositions according to the invention onto plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material. Preferably they are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
Various types of oils, wetters, adjuvants, fertilizer, or micronutrients may be added to the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
The user applies the agrochemical composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area. According to one embodiment, either individual components of the agrochemical composition according to the invention or partially premixed components may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
In a further embodiment, individual components of the agrochemical composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
The isoxazolo[5,4-b]pyridines of the formulae I. A, I.B or I.C (component A) and the at least one further herbicide of the formulae 11.1 or II.2 (component B) can be formulated and applied jointly or separately, simultaneously or in succession, before, during or after the emergence of the plants. In case of separate application, the order of the application of the components A and B is of minor importance. It is important that the at least one isoxazolo[5,4-b]pyridine of the formula I.A, I.B or I.C and the at least one further herbicide of the formulae 11.1 or II.2 are present simultaneously at the site of action, i.e. are at the same time in contact with or taken up by the plant to be controlled.
The compositions according to the invention are suitable as herbicides. They are suitable as such or as an appropriately formulated composition (agrochemical composition). The
compositions control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leafed weeds and grass weeds in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application. The compositions according to the invention are applied to the plants mainly by spraying the leaves. Here, the application can be carried out using, for example, water as carrier by customary spraying techniques using spray liquor amounts of from about 100 to 1000 l/ha (for example from 300 to 400 l/ha). The herbicidal compositions may also be applied by the low-volume or the ultra-low-volume method, or in the form of microgranules. Application of the herbicidal compositions according to the present invention can be done before, during and/or after, preferably during and/or after, the emergence of the undesirable plants. The herbicidal compositions according to the present invention can be applied pre- or post-emergence. If the active components A and B, and, if appropriate, C and/or D, are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by). Moreover, it may be advantageous to apply the compositions of the present invention on their own or jointly in combination with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria or with groups of active compounds which regulate growth. Also of interest is the miscibility with mineral salt solutions which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added.
When employed in plant protection, the amounts of active substances applied, i.e. components A and B, and, if appropriate, safeners C and/or further herbicides D, without formulation auxiliaries, are, depending on the kind of effect desired, from 0.001 to 3 kg/ha, preferably from 0.005 to 2.5 kg/ha and in particular from 0.01 to 2 kg/ha of active substance (a.s.).
In another preferred embodiment of the invention, the application rates of the isoxazolo[5,4- b]pyridine of formula I .A, I.B or I.C are in the range from 0.1 g/ha to 5000 g/ha and preferably in the range from 1 g/ha to 2500 g/ha, from 5 g/ha to 2000 g/ha, from 10 to 750 g/ha, more preferably from 50 to 500 g/ha.
The required application rates of herbicides B are generally in the range of from 0.5 to 2500 g/ha and preferably in the range of from 5 to 2000 g/ha, from 100 to 1500 g/h, most preferably from 100 to 500 g/ha of a.s..
The required application rates of safeners C are generally in the range of from 0.5 to 2500 g/ha and preferably in the range of from 5 to 2000 g/ha or 10 to 1000 g/ha of a.s..
Depending on the application method in question, the compositions can be employed in a number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec, altissima, Beta vulgaris spec, rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum,
(Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus,
Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Musa spec, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.
Preferred crops are Arachis hypogaea, Beta vulgaris spec, altissima, Brassica napus var.
napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Medicago sativa, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.
Especially preferred crops are crops of cereals, corn, soybeans, rice, millets, oilseed rape, cotton, sugarcane, potatoes, legumes, turf or permanent crops.
The compositions according to the invention can also be used in genetically modified plants. The term "genetically modified plants" is to be understood as plants whose genetic material has been modified by the use of recombinant DNA techniques to include an inserted sequence of DNA that is not native to that plant species' genome or to exhibit a deletion of DNA that was native to that species' genome, wherein the modification(s) cannot readily be obtained by cross breeding, mutagenesis or natural recombination alone. Often, a particular genetically modified plant will be one that has obtained its genetic modification(s) by inheritance through a natural breeding or propagation process from an ancestral plant whose genome was the one directly treated by use of a recombinant DNA technique. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides, e. g., by inclusion therein of amino acid mutation(s) that permit, decrease, or promote glycosylation or polymer additions such as prenylation, acetylation farnesylation, or PEG moiety attachment.
Plants that have been modified by breeding, mutagenesis or genetic engineering, e.g. have been rendered tolerant to applications of specific classes of herbicides, such as auxinic herbicides such as dicamba or 2,4-D; bleacher herbicides such as 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonylureas or imidazolinones; enolpyruvyl shikimate 3-phosphate synthase (EPSP) inhibitors such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors (PPO); lipid biosynthesis inhibitors such as acetylCoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering; furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxinic herbicides, or ACCase inhibitors. These herbicide resistance technologies are, for example, described in Pest
Management Science 61 , 2005, 246; 61 , 2005, 258; 61 , 2005, 277; 61 , 2005, 269; 61 , 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Science 57, 2009, 108; Australian Journal of
Agricultural Research 58, 2007, 708; Science 316, 2007, 1 185; and references quoted therein. Several cultivated plants have been rendered tolerant to herbicides by mutagenesis and conventional methods of breeding, e. g., Clearfield® summer rape (Canola, BASF SE,
Germany) being tolerant to imidazolinones, e. g., imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g., tribenuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate, imidazolinones and glufosinate, some of which are under development or commercially available under the brands or trade names
RoundupReady® (glyphosate tolerant, Monsanto, USA), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate tolerant, Bayer CropScience, Germany). Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as delta-endotoxins, e. g., CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g., VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g., Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3- hydroxy-steroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors);
stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as including pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g., WO 02/015701 ). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g., in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles (Coleoptera), two-winged insects (Diptera), and moths
(Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the CrylAb toxin), YieldGard® Plus (corn cultivars producing CrylAb and Cry3Bb1 toxins),
Starlink® (corn cultivars producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars producing the CrylAc toxin), Bollgard® I (cotton cultivars producing the CrylAc toxin), Bollgard® II (cotton cultivars producing CrylAc and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt1 1 (e. g., Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the CrylAb toxin and PAT enzyme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the Cry1 Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme). Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called
"pathogenesis-related proteins" (PR proteins, see, e.g., EP-A 392 225), plant disease resistance genes (e. g., potato culti-vars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato, Solanum bulbocastanum) or T4-lyso-zym (e.g., potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylovora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e.g., in the publications mentioned above.
Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g., bio-mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve human or animal nutrition, e. g., oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g., Nexera® rape, Dow AgroSciences, Canada).
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
Furthermore, it has been found that the the compositions according to the invention are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable. In this regard compositions have been found for the desiccation and/or defoliation of plants, processes for preparing these compositions, and methods for desiccating and/or defoliating plants using the compositions according to the invention.
As desiccants, the compositions according to the invention are suitable in particular for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.
Also of economic interest is the facilitation of harvesting, which is made possible by
concentrating within a certain period of time the dehiscence, or reduction of adhesion to the tree, in citrus fruit, olives and other species and varieties of pomaceous fruit, stone fruit and nuts. The same mechanism, i.e. the promotion of the development of abscission tissue between fruit part or leaf part and shoot part of the plants is also essential for the controlled defoliation of useful plants, in particular cotton.
Moreover, a shortening of the time interval in which the individual cotton plants mature leads to an increased fiber quality after harvesting.

Claims

Claims:
A herbicidal composition comprising as component
A) at l p consisting of
Figure imgf000028_0001
I.C
or an N-oxide, or an agriculturally useful salt thereof; and as component
B) at least one herbicide of the formula 11.1 , or an N-oxide, or an agriculturally useful salt thereof
Figure imgf000028_0002
wherein R1 is methyl or methoxy; R2 is hydrogen, methyl or ethoxy; and A is a heteroaryl group, which is unsubstituted or substituted with 1 , 2 or 3 radicals selected from the group consisiting of Ci-C6-alkyl or Ci-C6-haloalkyl; or a herbicide of the formula 11.2, or an N-oxide or an agriculturally useful salt thereof
Figure imgf000028_0003
wherein R1 is chlorine, methyl or methoxy; R2 is hydrogen, chlorine, methyl or ethoxy; and A is a heteroaryl group, which is unsubstituted or substituted with 1 , 2 or 3 radicals selected from the group consisiting of Ci-C6-alkyl or Ci-C6-haloalkyl.
Figure imgf000029_0001
ILK ILL
or an N-oxide, or an agriculturally useful salt thereof. The composition according to claim 1 or 2, wherein the component A is the compound of the formula I .A , or an N-oxide, or an agriculturally useful salt thereof.
The composition according to any one of claims 1 to 3, wherein the component B is the compound of the formula or 4R,5S-II.A, 4S,5S-II.A, or mixtures of these stereoisomers,
Figure imgf000030_0001
4R,5S-II.A 4S,5S-II.A
or compound II. D as defined in claim 2.
5. The composition according to claim 1 , wherein component A is the compound of the
formula I. A and the component B is selected from the stereoisomers of the compound of the formula II. C, {4R, 5R)-5-ethoxy-4-hydroxy-1 -methyl-3-[4-(trifluoromethyl)-2- pyridyl]imidazolidin-2-one and (4S, 5R)-5-ethoxy-4-hydroxy-1 -methyl-3-[4-(trifluoromethyl)- 2-pyridyl]imidazolidin-2-one, or mixtures of these stereoisomers.
6. The composition according to claim 1 , wherein component A is the compound of the
formula I. A and the component B is selected from the stereoisomers of the compound of the formula II. F, (4R, 5R)-1 -(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl- imidazolidin-2-one and (4R, 5S)-1 -(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl- imidazolidin-2-one, or mixtures of these stereoisomers.
7. The composition according to any one of claims 1 to 5, wherein the relative amount of the component A to the component B is from 20:1 to 1 :20.
8. The composition according to any one of claims 1 to 5, wherein the relative amount of the component A to the component B is from 5:1 to 1 :5.
9. The composition according to any one of claims 1 to 8 further comprising at least one
further herbicide D selected from the group consisting of atrazine, terbutylazine, mesotrione, bicyclopyron, S-metolachlor, topramezone, dicamba, bentazone, DMTA-p, pyroxasulfone, pendimethylin, atrazine, mesotrione and bicyclopyrone.
10. The composition according to any one of claims 1 to 9 further comprising as component C a safener.
1 1 . An agrochemical composition comprising a herbicidal composition as claimed in any one of claims 1 to 10, at least one inert liquid and/or solid carrier and, if desired, at least one further additive.
12. The use of a composition according to any one of claims 1 to 10 for controlling unwanted vegetation.
13. The use according to claim 12 in a crop field wherein the crop plants are selected from cereals, corn, soybean, rice, millet, oilseed rape, cotton, sugarcane, potatoes, legumes, turf and permanent crops.
14. A method for controlling unwanted vegetation, which comprises allowing a composition according to any one of claims 1 to 10 to act on plants, their seeds and/or their habitat.
PCT/EP2017/081426 2016-12-14 2017-12-05 Herbicidal compositions comprising isoxazolo[5,4-b]pyridines WO2018108612A1 (en)

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